#------------------------------------------------------------------------------ #$Date: 2023-05-06 11:49:18 +0100 (Sat, 06 May 2023) $ #$Revision: 283597 $ #$URL: svn://www.crystallography.net/cod/cif/2/24/42/2244243.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2244243 loop_ _publ_author_name 'Hebishy, Ali M. S.' 'Elgemeie, Galal H.' 'Gouda, Lobna M.' 'Jones, Peter G.' _publ_section_title ; Crystal structures of three homologues with increasing ring size: 2-meth-oxy-4-(thio-phen-2-yl)-5,6,7,8-tetra-hydro-quinoline-3-carbo-nitrile, 2-meth-oxy-4-(thio-phen-2-yl)-6,7,8,9-tetra-hydro-5H-cyclo-hepta-[b]pyridine-3-carbo-nitrile and 2-meth-oxy-4-(thio-phen-2-yl)-5,6,7,8,9,10-hexa-hydrocyclo-octa[b]pyridine-3-carbo-nitrile. ; _journal_coeditor_code YZ2030 _journal_issue 'Pt 4' _journal_name_full 'Acta crystallographica. Section E, Crystallographic communications' _journal_page_first 335 _journal_page_last 340 _journal_paper_doi 10.1107/S2056989023001883 _journal_volume 79 _journal_year 2023 _chemical_formula_iupac 'C16 H16 N2 O S' _chemical_formula_moiety 'C16 H16 N2 O S' _chemical_formula_sum 'C16 H16 N2 O S' _chemical_formula_weight 284.37 _chemical_name_systematic 2-Methoxy-4-(thiophen-2-yl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_method SHELXL-2018/3 _cell_angle_alpha 90 _cell_angle_beta 99.9254(18) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.68561(17) _cell_length_b 13.7435(2) _cell_length_c 12.0379(2) _cell_measurement_reflns_used 45134 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 76.6650 _cell_measurement_theta_min 4.9170 _cell_volume 1415.47(4) _computing_cell_refinement ; CrysAlisPro 1.171.42.57a (Rigaku OD, 2022) ; _computing_data_collection ; CrysAlisPro 1.171.42.57a (Rigaku OD, 2022) ; _computing_data_reduction ; CrysAlisPro 1.171.42.57a (Rigaku OD, 2022) ; _computing_molecular_graphics ; XP (Siemens, 1994) ; _computing_publication_material ; SHELXL2018/3 (Sheldrick, 2015b) ; _computing_structure_refinement ; SHELXL2018/3 (Sheldrick, 2015b) ; _computing_structure_solution ; SHELXT (Sheldrick, 2015a) ; _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 10.0000 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_unetI/netI 0.0058 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 5190 _diffrn_reflns_theta_full 77.000 _diffrn_reflns_theta_max 77.865 _diffrn_reflns_theta_min 4.926 _diffrn_source 'micro-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 1.998 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.83536 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlisPro; Rigaku OD, 2022) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.334 _exptl_crystal_description plate _exptl_crystal_F_000 600 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.202 _refine_diff_density_min -0.326 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 204 _refine_ls_number_reflns 5190 _refine_ls_number_restraints 51 _refine_ls_restrained_S_all 1.075 _refine_ls_R_factor_all 0.0294 _refine_ls_R_factor_gt 0.0285 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0429P)^2^+0.2180P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0758 _refine_ls_wR_factor_ref 0.0765 _reflns_number_gt 4977 _reflns_number_total 5190 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file yz2030sup1.cif _cod_data_source_block 1b _cod_depositor_comments 'Adding full bibliography for 2244242--2244244.cif.' _cod_original_cell_volume 1415.47(5) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2244243 _cod_database_fobs_code 2244243 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.754 _shelx_estimated_absorpt_t_max 0.943 _shelx_hkl_file ; 0 0 -2 123933. 352.586 1 0 0 4 24758.9 137.569 1 0 0 -6 2580.34 67.2702 1 5 0 3 52072.8 162.959 -2 0 0 8 52072.8 162.959 1 0 0 10 19562.6 78.3996 1 0 0 -12 1933.77 27.3864 1 0 0 14 1810.26 27.9302 1 0 1 1 13274.4 78.9612 1 0 -1 2 22838.6 95.4771 1 0 1 3 2971.59 38.8950 1 0 1 -4 7915.39 63.8970 1 0 1 -5 41254.8 164.280 1 0 1 6 5999.35 56.7951 1 0 -1 -7 15578.9 104.443 1 -5 1 -3 5522.09 33.7942 -2 0 -1 -8 5522.09 33.7942 1 0 -1 9 8361.98 31.9051 1 0 1 10 2936.01 23.8000 1 7 -1 4 4884.17 83.6899 -2 0 1 11 4884.17 83.6899 1 0 -1 12 1972.11 18.9629 1 -8 -1 -5 8610.81 61.6027 -2 0 1 -13 8610.81 61.6027 1 0 -1 14 202.594 9.12183 1 0 2 0 3540.99 33.5860 -2 0 -2 0 3540.99 33.5860 1 0 -2 -1 58785.4 168.997 1 0 2 -2 1493.62 56.0753 1 0 -2 3 13793.7 110.669 1 0 -2 4 28119.7 151.461 1 0 2 -6 223.464 17.7355 1 0 2 -7 1332.16 30.1844 1 -5 -2 -3 28776.3 83.0728 -2 0 2 -8 28776.3 83.0728 1 0 -2 -9 157.206 8.04512 1 0 -2 -10 322.467 10.2351 1 7 -2 4 9306.98 90.0626 -2 0 2 11 9306.98 90.0626 1 0 -2 12-0.11385 7.37545 1 8 -2 5 8151.59 75.6502 -2 0 2 13 8151.59 75.6502 1 0 2 14 393.872 11.8944 1 0 -3 -1 51941.2 186.684 1 0 -3 2 611.131 21.5618 1 0 3 3 872.905 23.4406 1 0 3 4 36825.7 138.009 1 0 -3 6 529.744 17.7392 1 0 3 7 6059.67 33.7722 1 5 -3 3 15775.2 63.2277 -2 0 3 8 15775.2 63.2277 1 0 3 9 6936.24 32.2875 1 0 -3 -10 450.968 10.9025 1 7 3 4 1575.09 53.9400 -2 0 -3 11 1575.09 53.9400 1 0 3 -12 3391.77 22.3124 1 -8 -3 -5 1017.75 22.0450 -2 0 3 -13 1017.75 22.0450 1 0 -3 14 809.502 17.0587 1 0 -4 0 1630.06 52.8269 -2 0 4 0 1630.06 52.8269 1 0 -4 -1 2699.54 33.4368 1 0 -4 2 14018.5 75.5897 1 0 4 -3 53252.6 184.242 1 0 4 4 865.640 16.7522 1 0 4 6 5386.76 52.0021 1 0 4 7 1931.28 15.7765 1 5 4 3 11007.9 52.9304 -2 0 -4 8 11007.9 52.9304 1 0 -4 9 4910.10 25.4220 1 0 4 10 2321.57 19.4446 1 7 4 4 11497.4 126.904 -2 0 -4 11 11497.4 126.904 1 0 -4 12 1664.30 16.3213 1 8 4 5 4810.73 38.8075 -2 0 -4 13 4810.73 38.8075 1 0 -4 14 2217.11 23.2348 1 0 -5 1 69564.4 252.486 1 0 -5 -2 451.249 13.8469 1 0 -5 3 281.332 11.1923 1 0 5 -4 8396.57 48.9651 1 3 5 2 6490.68 149.282 -2 0 -5 5 6490.68 149.282 1 0 5 6 8107.39 41.1435 1 0 5 7 133.129 6.15090 1 -5 5 -3 2159.53 22.1482 -2 0 -5 -8 2159.53 22.1482 1 0 5 9 19102.9 65.5876 1 0 5 10 13893.9 44.6956 1 7 5 4 6108.61 108.305 -2 0 -5 11 6108.61 108.305 1 0 5 -12 1773.19 18.8429 1 -8 -5 -5 1414.38 26.6818 -2 0 5 -13 1414.38 26.6818 1 0 5 -14 688.394 13.3214 1 0 -6 0 1182.09 42.6852 -2 0 6 0 1182.09 42.6852 1 0 -6 1 176.627 18.7828 1 0 -6 -2 2887.89 28.3948 1 0 -6 4 53086.5 125.193 1 -3 -6 -2 1990.02 39.6412 -2 0 6 -5 1990.02 39.6412 1 0 -6 6 8947.29 28.8156 1 0 6 -7 591.643 8.50132 1 5 -6 3 2416.25 21.9702 -2 0 6 8 2416.25 21.9702 1 0 6 9 32.8460 7.38751 1 0 6 -10 5627.09 29.6609 1 7 -6 4 1393.25 38.6769 -2 0 6 11 1393.25 38.6769 1 0 6 12 966.946 16.3308 1 -8 -6 -5 216.515 18.2886 -2 0 6 -13 216.515 18.2886 1 0 6 -14 2834.01 37.7545 1 0 -7 1 36.4495 14.1197 1 0 -7 -2 10986.1 67.7461 1 -2 -7 -1 4329.92 58.4409 -2 0 7 -3 4329.92 58.4409 1 0 -7 4 11058.3 44.6223 1 -3 -7 -2 2708.69 29.2173 -2 0 7 -5 2708.69 29.2173 1 0 -7 6 5673.35 20.6689 1 0 7 7 194.602 6.65894 1 5 7 3 2656.48 23.0730 -2 0 -7 8 2656.48 23.0730 1 0 7 -9 2217.32 17.8865 1 0 7 10 1219.82 14.7453 1 7 -7 4 1447.62 41.5060 -2 0 7 11 1447.62 41.5060 1 0 7 -12 61.5572 7.95126 1 8 -7 5 395.952 26.5600 -2 0 7 13 395.952 26.5600 1 0 8 0 602.315 29.3931 -2 0 -8 0 602.315 29.3931 1 0 -8 1 3376.39 34.4731 1 0 8 -2 9.01011 10.0763 1 -2 -8 -1 4123.22 56.9214 -2 0 8 -3 4123.22 56.9214 1 0 -8 4 6527.64 27.1135 1 3 -8 2 2800.64 24.5277 -2 0 8 5 2800.64 24.5277 1 0 8 6 6388.68 27.7921 1 0 8 -7 5166.29 27.6034 1 5 -8 3 5345.44 41.4285 -2 0 8 8 5345.44 41.4285 1 0 8 9 36.2355 7.56886 1 0 8 10 5870.94 31.6916 1 -7 -8 -4 1367.37 55.5647 -2 0 8 -11 1367.37 55.5647 1 0 -8 12 10.5097 7.62230 1 -8 -8 -5 6778.74 64.9049 -2 0 8 -13 6778.74 64.9049 1 0 -9 1 707.959 11.4334 1 0 -9 -2 24715.3 66.1741 1 -2 -9 -1 7329.42 68.5824 -2 0 9 -3 7329.42 68.5824 1 0 9 -4 865.939 11.5376 1 3 -9 2 2463.40 24.5610 -2 0 9 5 2463.40 24.5610 1 0 9 -6 2326.78 16.8352 1 0 9 -7 3868.65 22.9505 1 -5 -9 -3 13049.4 63.6406 -2 0 9 -8 13049.4 63.6406 1 0 -9 -9 3546.58 28.5460 1 0 -9 10 1463.52 19.3578 1 7 -9 4 64.2043 49.9757 -2 0 9 11 64.2043 49.9757 1 0 9 12 3142.64 27.7242 1 0 10 0 10749.0 63.4978 -2 0 -10 0 10749.0 63.4978 1 0 -10 1 13618.4 50.8465 1 0 -10 -2 1700.49 16.1880 1 -2 -10 -1 15347.3 136.518 -2 0 10 -3 15347.3 136.518 1 0 10 4 119.193 7.38813 1 3 10 2 2518.73 24.4322 -2 0 -10 5 2518.73 24.4322 1 0 10 -6 5465.00 27.0114 1 0 10 -7 33916.1 88.0177 1 -5 -10 -3 5685.83 49.1144 -2 0 10 -8 5685.83 49.1144 1 0 10 -9 2544.52 31.1673 1 0 10 10 747.134 17.3639 1 7 -10 4 1829.90 69.3919 -2 0 10 11 1829.90 69.3919 1 0 10 12 19.7684 8.11696 1 0 -11 1 59.1679 8.57422 1 0 11 2 6874.69 33.5899 1 2 -11 1 10581.1 110.202 -2 0 11 3 10581.1 110.202 1 0 11 4 88.2395 8.43016 1 -3 -11 -2 2591.71 26.5943 -2 0 11 -5 2591.71 26.5943 1 0 11 -6 23.8807 7.45608 1 0 -11 7 2718.19 24.3113 1 -5 -11 -3 5854.15 47.5305 -2 0 11 -8 5854.15 47.5305 1 0 11 -9 104.856 11.4650 1 0 11 10 1057.52 19.8642 1 0 11 -11 1446.12 21.6690 1 0 -12 0 38343.5 149.463 -2 0 12 0 38343.5 149.463 1 0 -12 -1 20.6541 8.45367 1 0 12 2 1339.79 16.2868 1 2 12 1 660.257 32.1955 -2 0 -12 3 660.257 32.1955 1 0 12 -4 2731.68 21.2737 1 3 12 2 267.418 17.7531 -2 0 -12 5 267.418 17.7531 1 0 12 -6 73.0325 8.03076 1 0 -12 -7 646.362 13.8199 1 5 -12 3 1598.11 26.2561 -2 0 12 8 1598.11 26.2561 1 0 12 -9 89.7956 9.00921 1 0 -12 10 2453.08 26.5844 1 0 13 1 2399.06 24.6442 1 0 -13 2 3735.35 24.7472 1 2 13 1 1658.85 31.9635 -2 0 -13 3 1658.85 31.9635 1 0 13 -4 417.032 10.7534 1 -3 -13 -2 16403.6 62.0961 -2 0 13 -5 16403.6 62.0961 1 0 13 6 1273.14 21.0436 1 0 -13 7 145.382 10.6695 1 5 13 3 1542.73 25.5122 -2 0 -13 8 1542.73 25.5122 1 0 13 -9 2463.62 34.3198 1 0 -14 0 98.2004 15.0265 -2 0 14 0 98.2004 15.0265 1 0 -14 1 1307.99 15.9897 1 0 14 2 534.681 12.0353 1 2 -14 1 2506.87 35.4926 -2 0 14 3 2506.87 35.4926 1 0 14 4 4142.08 26.8956 1 3 -14 2 121.773 13.7886 -2 0 14 5 121.773 13.7886 1 0 -14 6 583.386 13.4851 1 0 14 -7 3269.91 30.8165 1 5 14 3 1027.39 28.5153 -2 0 -14 8 1027.39 28.5153 1 0 -15 -1 37.8519 8.37529 1 0 -15 2 1099.49 13.9334 1 -2 -15 -1 1919.65 27.0039 -2 0 15 -3 1919.65 27.0039 1 0 15 -4 2082.90 21.3958 1 3 -15 2 7386.75 48.2118 -2 0 15 5 7386.75 48.2118 1 0 -15 6 2006.54 21.9845 1 0 15 7 50.6703 7.35685 1 0 -16 0 1005.92 24.1350 -2 0 16 0 1005.92 24.1350 1 0 -16 -1 4264.98 26.0103 1 0 -16 2 11.9540 7.65906 1 -2 -16 -1 1637.89 31.0641 -2 0 16 -3 1637.89 31.0641 1 0 16 4 1626.85 22.8458 1 3 -16 2 554.212 13.5551 -2 0 16 5 554.212 13.5551 1 0 17 -1 36.0133 6.52508 1 0 17 2 798.771 14.7722 1 2 -17 1 264.444 27.7709 -2 0 17 3 264.444 27.7709 1 -1 0 15 1307.47 20.1992 1 1 0 -13 90.2478 11.1213 1 -1 0 11 29.9427 11.2432 1 -6 0 -2 5744.38 52.6094 -2 1 0 -9 5744.38 52.6094 1 -1 0 7 10338.0 69.0211 1 1 0 -5 28683.6 168.229 1 1 0 -3 85710.7 286.575 1 -1 0 1 32695.7 193.505 -2 1 0 -1 32695.7 193.505 1 1 0 1 21731.6 98.1805 1 -1 0 -3 91945.5 334.031 1 1 0 5 56.7017 15.6616 1 -4 0 -4 21101.3 125.191 -2 -1 0 -7 21101.3 125.191 1 -1 0 -9 243.025 13.3939 1 -1 0 -11 1444.50 21.2123 1 1 0 13 617.647 16.3248 1 -1 -1 15 195.804 8.90880 1 9 1 4 3231.62 64.7290 -2 -1 -1 14 3231.62 64.7290 1 -1 1 13 1119.63 13.7432 1 -1 -1 12 1578.38 17.1166 1 -1 -1 11 17.7474 8.82975 1 -1 -1 10 6529.63 35.2261 1 -6 -1 -2 6336.32 34.7861 -2 1 1 -9 6336.32 34.7861 1 -1 1 8 4742.74 23.3986 1 1 -1 -7 282.713 13.4002 1 1 -1 -6 4314.19 35.5261 1 -1 1 5 60.9707 11.3949 1 1 1 -4 70.9967 11.9278 1 1 -1 -3 12617.8 69.5379 1 -1 1 2 526.515 13.5332 1 1 1 -1 85951.8 279.271 -2 -1 -1 1 85951.8 279.271 1 1 1 0 59850.9 199.006 1 1 -1 1 60634.6 188.246 1 1 1 2 12986.7 61.1634 1 1 -1 3 4293.82 42.0314 1 1 -1 4 8318.32 70.4257 1 -1 1 -5 22503.4 123.019 1 -1 -1 -6 14955.1 121.216 1 -4 -1 -4 1084.27 19.7350 -2 -1 1 -7 1084.27 19.7350 1 1 1 8 6301.70 37.5054 1 1 1 9 1119.42 14.7135 1 6 -1 5 3374.85 40.1845 -2 1 1 10 3374.85 40.1845 1 1 -1 11 239.751 10.6405 1 7 1 6 9249.32 77.1767 -2 1 -1 12 9249.32 77.1767 1 -1 -1 -13 37.6766 7.49828 1 1 1 14 986.771 19.3361 1 -1 -2 15 9.10808 7.20252 1 9 2 4 1122.66 44.8020 -2 -1 -2 14 1122.66 44.8020 1 1 2 -13 6296.86 31.4994 1 1 -2 -12 3997.41 26.3255 1 1 2 -11 2853.22 21.1309 1 1 2 -10 8413.07 38.3310 1 6 2 2 17883.1 60.8725 -2 -1 -2 9 17883.1 60.8725 1 -1 2 8 1075.33 13.6504 1 1 2 -7 151.097 13.2992 1 1 2 -6 1934.68 23.7410 1 1 -2 -5 25590.8 105.323 1 -1 -2 4 7405.92 39.7482 1 1 2 -3 62251.6 156.557 1 -1 2 2 67.8261 10.6028 1 1 2 -1 102391. 196.925 -2 -1 -2 1 102391. 196.925 1 1 2 0 6001.45 54.4634 1 -1 2 -1 460.288 19.6323 1 1 2 2 35811.4 155.665 1 -1 2 -3 1601.09 30.0239 1 1 -2 4 14191.1 117.337 1 -1 -2 -5 75687.6 273.082 1 -1 -2 -6 1810.24 31.7026 1 -4 2 -4 24175.0 98.3926 -2 -1 -2 -7 24175.0 98.3926 1 1 -2 8 20010.6 53.0468 1 1 -2 9 9034.66 37.4986 1 6 2 5 4415.22 54.9299 -2 1 -2 10 4415.22 54.9299 1 -1 2 -11 2938.63 25.4686 1 7 2 6 9379.88 55.5796 -2 1 -2 12 9379.88 55.5796 1 1 -2 13 173.446 9.03030 1 1 2 14 37.0343 7.12318 1 9 3 4 244.364 31.4036 -2 -1 -3 14 244.364 31.4036 1 1 3 -13 2428.53 26.1927 1 -1 3 12 1087.34 14.7072 1 -1 -3 11 2539.29 20.1528 1 -1 -3 10 786.331 13.8500 1 6 3 2 5991.83 34.8086 -2 -1 -3 9 5991.83 34.8086 1 1 3 -8 157.271 7.13270 1 1 3 -7 37018.9 103.200 1 1 -3 -6 19332.5 76.5839 1 1 -3 -5 28980.5 93.1090 1 -1 3 4 13731.2 69.4104 1 -1 -3 3 7936.46 43.2723 1 1 -3 -2 172.088 13.2526 1 -1 3 1 116905. 451.047 -2 1 -3 -1 116905. 451.047 1 -1 -3 0 62054.4 191.267 1 -1 -3 -1 8541.66 58.6681 1 1 -3 2 7566.42 52.6348 1 -1 3 -3 30747.0 149.095 1 2 3 3 9532.06 97.9007 -2 1 -3 4 9532.06 97.9007 1 1 3 5 201.303 18.9918 1 -1 3 -6 1192.77 27.1428 1 -4 -3 -4 19912.1 63.4183 -2 -1 3 -7 19912.1 63.4183 1 1 -3 8 1.01794 6.26026 1 1 3 9 17249.4 60.1418 1 6 3 5 2053.83 37.6437 -2 1 -3 10 2053.83 37.6437 1 -1 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8 6 -1 1.65002 7.28076 2 8 -6 1 1327.24 14.1348 2 8 -6 2 3236.63 24.4670 2 8 6 3 488.811 10.9130 2 8 6 4 29.2473 7.10948 2 8 6 6 6074.90 39.9157 2 8 7 -10 1721.46 23.0423 2 -8 7 9 15.1832 6.17804 2 8 7 -7 1908.46 15.4008 2 8 7 -6 558.370 9.99899 2 8 7 -5 257.184 8.55875 2 8 -7 -4 163.811 9.02416 2 8 7 -3 3780.78 28.2574 2 8 7 -2 2392.86 20.3527 2 8 7 -1 196.023 9.74592 2 8 -7 1 6737.97 37.9460 2 8 -7 2 541.656 11.3616 2 8 -7 3 1090.59 14.1762 2 8 7 4 384.133 11.8205 2 8 -7 6 3116.40 29.5130 2 -8 8 9 36.8585 5.85365 2 8 8 -7 758.954 11.5202 2 8 8 -6 915.943 12.1711 2 8 -8 -5 2162.55 19.7667 2 8 8 -4 4125.18 26.0397 2 8 8 -3 3151.08 23.0597 2 8 8 -2 45.8200 9.43555 2 8 8 -1 2202.94 19.9034 2 8 -8 1 222.485 9.94541 2 8 8 2 1304.75 18.5654 2 8 -8 3 1080.78 17.4191 2 8 -8 4 141.470 8.48791 2 8 9 -7 752.564 14.2962 2 8 9 -6 3449.39 30.6978 2 8 -9 -5 686.357 10.8417 2 8 9 -4 380.535 11.4892 2 8 9 -3 1126.03 15.9703 2 8 9 -2 866.325 14.6531 2 8 -9 -1-0.49205 7.37645 2 8 -9 1 547.437 12.5841 2 8 -9 2 48.0221 8.33077 2 8 -9 3 121.098 8.37962 2 -8 -9 -4 363.547 13.4098 2 -8 10 7 482.199 12.2088 2 8 10 -6 114.408 7.45345 2 -8 10 5 1533.11 20.2872 2 8 10 -4 562.558 11.3786 2 8 10 -3-7.53063 6.79667 2 8 10 -2 2166.78 23.0023 2 8 -10 -1 1526.16 17.4764 2 -8 -10 -1 426.850 12.3234 2 8 -10 2 6.45942 7.03420 2 -8 -10 -3 2618.81 28.6460 2 8 11 -5 104.086 7.50304 2 8 11 -4 1293.80 21.1026 2 -8 11 3 29.8071 6.40420 2 -8 11 2 57.5643 8.68649 2 -8 11 1 4296.33 58.0851 2 8 -11 1 0.00180 9.87711 2 9 0 -7 561.415 17.7959 2 9 0 -5 8992.35 58.2055 2 9 0 -3 136.728 11.0190 2 9 0 1 238.142 14.9225 2 9 0 3 4854.68 42.3166 2 9 0 5 846.973 27.3215 2 -9 1 10 1664.24 18.8494 2 9 1 -8 2096.96 21.5113 2 9 1 -7 1058.84 15.7331 2 -9 -1 6 224.077 8.37767 2 9 1 -5 1424.57 14.5312 2 9 -1 -4 4411.13 24.6563 2 9 -1 -3 171.878 8.71663 2 9 -1 -2 3137.26 23.2890 2 9 -1 0 79.7427 7.89975 2 9 -1 1 2320.61 24.2730 2 9 1 2 2868.50 23.4482 2 9 -1 3 846.335 14.3594 2 9 -1 5 3671.56 32.2706 2 9 -1 6 546.341 13.7674 2 -9 2 10 525.485 11.3402 2 9 2 -8 1816.68 19.9093 2 9 2 -7 19.2087 7.44179 2 9 2 -6 1170.02 13.8504 2 -9 -2 5 586.219 10.4332 2 9 -2 -4 2442.73 17.4300 2 9 -2 -3 11557.0 45.7265 2 9 -2 -2 16.1599 7.01443 2 9 -2 0 12278.4 52.3840 2 9 -2 1 598.541 12.4987 2 9 -2 2 4759.10 29.8227 2 9 2 3 503.814 10.4771 2 9 -2 5 21.7464 8.81151 2 9 -2 6 194.671 11.0717 2 -9 -3 10 312.891 8.54866 2 9 3 -8 294.410 10.1173 2 9 3 -7 359.518 9.85901 2 9 3 -6 1417.09 16.0415 2 9 3 -5 2476.98 19.4771 2 9 -3 -4 8692.05 39.2883 2 9 -3 -3 774.737 12.4865 2 9 -3 -2 243.364 8.51841 2 9 -3 0 287.075 9.23055 2 9 -3 1 2659.28 23.1517 2 9 -3 2 225.872 9.74345 2 9 -3 3 14.0047 7.43465 2 9 -3 5 701.002 14.9798 2 9 -3 6 304.964 13.0196 2 9 4 -10 15.4669 12.2170 2 -9 -4 8 10.7071 7.21889 2 -9 4 7 1945.45 19.2439 2 9 4 -6 1292.85 14.3731 2 9 4 -5 1477.63 15.3654 2 9 4 -4 5287.27 29.9916 2 9 -4 -3 88.6512 7.62639 2 9 -4 -2 224.872 9.06424 2 9 -4 0 2115.64 18.9943 2 9 -4 1 2291.88 19.2195 2 9 -4 2 83.5192 7.54433 2 9 -4 3 480.682 11.2593 2 9 -4 5 2325.65 28.0256 2 -9 5 8 13.9756 5.81532 2 -9 -5 7 25.6666 6.44113 2 9 5 -6 75.6433 7.69898 2 9 5 -5 42.4367 8.42065 2 9 -5 -4 255.586 9.63158 2 9 -5 -3 142.130 9.48694 2 9 -5 -2 1182.41 17.4633 2 9 -5 0 5.37861 7.22161 2 9 -5 1 493.239 10.0865 2 9 -5 2 130.219 7.14985 2 9 -5 3 1315.96 14.7463 2 9 -5 5 25.3869 10.6453 2 -9 6 8 168.660 7.41387 2 -9 6 7 1002.28 14.7881 2 -9 6 6 659.707 12.6776 2 9 -6 -5 2685.56 24.1353 2 9 -6 -4-4.87186 7.95920 2 9 -6 -3 51.0594 7.96300 2 9 -6 -2 104.301 8.51460 2 9 -6 0 848.419 15.6817 2 9 6 1 1034.90 14.7081 2 9 -6 2 1465.19 15.8302 2 9 -6 3 5340.87 34.5748 2 9 6 4 18.0855 7.96693 2 9 -7 -8 2426.12 26.1878 2 -9 7 7 93.0837 7.75563 2 -9 7 6 162.030 9.00496 2 9 -7 -5 1206.48 14.5816 2 9 -7 -4 84.7346 7.59903 2 9 -7 -3 278.950 8.93360 2 9 -7 -2 4059.35 32.0195 2 9 -7 0 1038.40 17.2750 2 9 7 1 1173.07 15.4929 2 9 7 2 1451.40 17.5074 2 9 7 3 580.413 12.5231 2 -9 8 7 7971.12 41.0198 2 9 8 -6 750.542 14.4179 2 9 -8 -5 645.311 10.9528 2 9 -8 -4 2514.73 22.5021 2 9 -8 -3 1545.92 17.2128 2 9 -8 -2 739.592 12.0067 2 9 8 0 729.211 15.9529 2 9 8 1 5.65739 7.23086 2 9 -8 2 23.9443 9.09551 2 -9 9 5 159.804 11.1695 2 -9 9 4 399.060 9.66819 2 9 -9 -3 222.097 7.87857 2 9 -9 -2 721.398 12.9780 2 9 -9 0-3.83114 7.53991 2 9 -9 1 219.128 11.8150 2 -9 -10 2 659.811 29.6363 2 -10 0 8 89.7748 8.77414 2 -10 0 6 142.608 14.8812 2 10 0 -4 19437.9 81.8818 2 10 0 0 1397.19 20.4365 2 -10 0 -2 14.6620 8.30209 2 -10 1 8 311.014 8.54711 2 10 1 -7 1912.12 26.9245 2 10 1 -6 1019.42 14.4643 2 10 1 -5 9341.25 48.8986 2 10 1 -4 9.96134 6.15504 2 10 -1 -3 2971.71 21.1332 2 10 -1 -1 1334.14 14.2787 2 10 -1 0 783.296 12.5278 2 10 -1 1 23.1427 7.45530 2 10 1 2 860.076 13.5971 2 10 1 3 4773.13 32.5635 2 -10 2 8 548.580 10.4998 2 10 -2 -7 433.090 10.9917 2 10 -2 -6 2715.73 22.8857 2 10 -2 -5 1162.30 18.2584 2 10 -2 -4 1632.81 16.1489 2 10 2 -3 64.4814 6.65067 2 10 -2 -1 437.512 10.2233 2 10 -2 0 1154.86 13.6912 2 10 -2 1 99.1763 6.48125 2 10 -2 2 137.859 7.85466 2 10 2 3 12.4804 7.99858 2 -10 -3 7-4.82331 6.56513 2 10 -3 -6 58.3054 7.94581 2 10 -3 -5 719.334 14.5847 2 10 -3 -4 806.079 12.4875 2 10 -3 -3 142.569 7.96101 2 10 -3 -1 31.3045 6.76800 2 10 -3 0 1248.76 15.7589 2 10 -3 1 1442.08 18.7764 2 10 -3 2 937.477 16.2654 2 10 -3 3 818.935 22.9467 2 10 -4 -7 64.6587 6.84964 2 10 -4 -6 612.925 11.3554 2 10 -4 -5 1221.23 17.9915 2 10 -4 -4 6.71925 7.71134 2 10 -4 -3 2327.94 18.6416 2 10 4 -1 1344.62 16.2521 2 10 4 0 133.914 8.37282 2 10 -4 1 559.161 13.6412 2 10 -4 2 158.179 7.97550 2 10 -5 -6 370.718 10.6104 2 -10 5 5 842.130 13.5353 2 10 5 -4 2680.46 27.8663 2 10 -5 -3 1513.82 19.0089 2 10 5 -1 1347.72 16.0304 2 10 5 0 2872.39 23.6396 2 10 5 1 45.7472 6.90451 2 10 5 2-2.17565 10.5658 2 10 -6 -5 10.3840 7.09347 2 10 -6 -4 5070.58 40.1912 2 10 -6 -3 1.30607 7.54771 2 10 6 -1 1956.57 21.2342 2 10 6 0 205.435 11.6151 2 10 -6 1 1063.23 24.4473 2 -10 7 3 191.048 8.66803 2 10 -7 -1 281.129 16.3968 2 0 0 0 0.00000 0.00000 0 TITL quik_m7_twin1_hklf4 in P2(1)/n REM P2(1)/n (#14 in standard setting) CELL 1.54184 8.685609 13.743509 12.037945 90.0000 99.9254 90.0000 ZERR 4.00 0.000083 0.000120 0.000116 0.0000 0.0009 0.0000 LATT 1 SYMM -x+1/2, y+1/2,-z+1/2 SFAC C H N O S UNIT 64.00 64.00 8.00 4.00 4.00 REM CrysAlisPro recorded range (K): Min=99.9; max=100.1; aver:100.0 TEMP -173 TREF HKLF 5 BASF 0.51206 END ; _shelx_hkl_checksum 2463 _shelx_res_file ; TITL quik_m7_5 in P2(1)/n shelx.res created by SHELXL-2018/3 at 09:32:45 on 19-Jan-2023 CELL 1.54184 8.685609 13.743509 12.037945 90 99.9254 90 ZERR 4 0.00017 0.00024 0.00023 0 0.0018 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O S UNIT 64 64 8 4 4 L.S. 10 PLAN 10 SIZE 0.15 0.08 0.03 TEMP -173 FMAP 2 ACTA 154 BOND $H PLAN 10 CONF REM Instructions for potential hydrogen bonds EQIV $1 -x+3/2, y-1/2, -z+1/2 HTAB C13 N2_$1 EQIV $2 -x+1, -y+1, -z HTAB C15 N2_$2 WGHT 0.042900 0.218000 BASF 0.49823 FVAR 5.39101 0.91652 N1 3 0.623909 0.400932 0.555821 11.00000 0.02338 0.02470 = 0.01966 0.00085 0.00470 0.00422 C2 1 0.687551 0.448407 0.479705 11.00000 0.02060 0.01949 = 0.02242 -0.00093 0.00371 0.00345 C3 1 0.646215 0.432572 0.363194 11.00000 0.01960 0.01829 = 0.02077 0.00145 0.00491 0.00246 C4A 1 0.461751 0.312523 0.404943 11.00000 0.01994 0.01939 = 0.02195 0.00341 0.00537 0.00355 C5 1 0.331889 0.239669 0.371292 11.00000 0.02364 0.02463 = 0.02264 0.00422 0.00631 -0.00177 AFIX 23 H5A 2 0.299458 0.241721 0.288350 11.00000 -1.20000 H5B 2 0.240830 0.259286 0.405503 11.00000 -1.20000 AFIX 0 C6 1 0.376340 0.134618 0.406725 11.00000 0.03393 0.02239 = 0.03151 0.00260 0.01417 -0.00152 AFIX 23 H6A 2 0.306161 0.089483 0.357744 11.00000 -1.20000 H6B 2 0.484451 0.121942 0.394673 11.00000 -1.20000 AFIX 0 C7 1 0.366009 0.113318 0.529559 11.00000 0.03376 0.02371 = 0.03262 0.00936 0.01314 0.00411 AFIX 23 H7A 2 0.391137 0.043785 0.544622 11.00000 -1.20000 H7B 2 0.256606 0.123530 0.540072 11.00000 -1.20000 AFIX 0 C8 1 0.472425 0.174196 0.616977 11.00000 0.03220 0.03223 = 0.02876 0.01270 0.00824 0.00513 AFIX 23 H8A 2 0.582141 0.161925 0.608561 11.00000 -1.20000 H8B 2 0.460131 0.151458 0.692992 11.00000 -1.20000 AFIX 0 C9 1 0.443301 0.284690 0.610469 11.00000 0.02920 0.03076 = 0.02112 0.00369 0.00848 0.00194 AFIX 23 H9A 2 0.329164 0.296497 0.597463 11.00000 -1.20000 H9B 2 0.488083 0.314069 0.684049 11.00000 -1.20000 AFIX 0 C9A 1 0.511989 0.335084 0.519223 11.00000 0.02214 0.02107 = 0.02221 0.00282 0.00647 0.00505 O1 4 0.799883 0.515048 0.512574 11.00000 0.02627 0.02676 = 0.02149 -0.00295 0.00175 -0.00317 C10 1 0.854615 0.523472 0.631981 11.00000 0.02958 0.02914 = 0.02138 -0.00357 -0.00158 0.00196 AFIX 137 H10A 2 0.939489 0.571270 0.645841 11.00000 -1.50000 H10B 2 0.893140 0.460149 0.662292 11.00000 -1.50000 H10C 2 0.768497 0.544735 0.669146 11.00000 -1.50000 AFIX 0 C11 1 0.721025 0.490021 0.288375 11.00000 0.02042 0.01988 = 0.02130 -0.00310 0.00277 0.00055 N2 3 0.782439 0.538791 0.231939 11.00000 0.02681 0.02548 = 0.02517 -0.00122 0.00623 -0.00486 SAME C4 C12' S1' C13' C14' C15' SIMU C4 > C15' 0.02 0.04 0.9 C4 1 0.533786 0.361418 0.325159 11.00000 0.01921 0.01838 = 0.01993 0.00200 0.00410 0.00364 PART 1 21 C12 1 0.495550 0.337234 0.203506 21.00000 0.01888 0.01940 = 0.01978 0.00311 0.00470 -0.00130 S1 5 0.413978 0.421396 0.104273 21.00000 0.02551 0.02386 = 0.02084 0.00618 0.00265 0.00268 C13 1 0.512186 0.247790 0.156113 21.00000 0.02993 0.02497 = 0.01795 0.00208 0.00576 -0.00210 AFIX 43 H13 2 0.554088 0.192012 0.197180 21.00000 -1.20000 AFIX 0 C14 1 0.458075 0.249439 0.036467 21.00000 0.03022 0.02755 = 0.02299 -0.00496 0.00822 -0.00859 AFIX 43 H14 2 0.461758 0.194492 -0.010884 21.00000 -1.20000 AFIX 0 C15 1 0.400772 0.337952 -0.002424 21.00000 0.02696 0.03791 = 0.01764 0.00142 0.00320 -0.00524 AFIX 43 H15 2 0.358864 0.351468 -0.079069 21.00000 -1.20000 AFIX 0 PART 2 -21 FLAT S1' > C15' S1' 5 0.497321 0.243843 0.135351 -21.00000 0.03439 C12' 1 0.482286 0.348714 0.203476 -21.00000 0.02104 C13' 1 0.415650 0.412999 0.128163 -21.00000 0.07921 AFIX 43 H13' 2 0.391857 0.477403 0.148342 -21.00000 -1.20000 AFIX 0 C14' 1 0.383095 0.379725 0.017920 -21.00000 0.03664 AFIX 43 H14' 2 0.339750 0.418697 -0.044909 -21.00000 -1.20000 AFIX 0 C15' 1 0.420700 0.285207 0.011227 -21.00000 0.02622 AFIX 43 H15' 2 0.404855 0.247901 -0.056219 -21.00000 -1.20000 AFIX 0 HKLF 5 REM quik_m7_5 in P2(1)/n REM wR2 = 0.0765, GooF = S = 1.071, Restrained GooF = 1.075 for all data REM R1 = 0.0285 for 4977 Fo > 4sig(Fo) and 0.0294 for all 5190 data REM 204 parameters refined using 51 restraints END WGHT 0.0429 0.2181 REM Highest difference peak 0.202, deepest hole -0.326, 1-sigma level 0.040 Q1 1 0.4945 0.3363 0.3632 11.00000 0.05 0.20 Q2 1 0.5094 0.3475 0.2581 11.00000 0.05 0.20 Q3 1 0.6825 0.4283 0.4125 11.00000 0.05 0.18 Q4 1 0.4067 0.2748 0.3829 11.00000 0.05 0.15 Q5 1 0.6725 0.4576 0.3369 11.00000 0.05 0.15 Q6 1 0.4892 0.3180 0.4613 11.00000 0.05 0.15 Q7 1 0.5872 0.3993 0.3396 11.00000 0.05 0.14 Q8 1 0.4846 0.3057 0.5594 11.00000 0.05 0.14 Q9 1 0.2341 0.1390 0.5729 11.00000 0.05 0.12 Q10 1 0.4554 0.2316 0.6032 11.00000 0.05 0.12 ; _shelx_res_checksum 61417 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N N1 0.62391(11) 0.40093(7) 0.55582(8) 0.0225(2) Uani d 1 . . C C2 0.68755(12) 0.44841(8) 0.47970(9) 0.0208(2) Uani d 1 . . C C3 0.64622(12) 0.43257(7) 0.36319(9) 0.0194(2) Uani d 1 . . C C4A 0.46175(12) 0.31252(8) 0.40494(9) 0.0202(2) Uani d 1 . . C C5 0.33189(13) 0.23967(8) 0.37129(9) 0.0234(2) Uani d 1 . . H H5A 0.299458 0.241721 0.288350 0.028 Uiso calc 1 . . H H5B 0.240830 0.259286 0.405503 0.028 Uiso calc 1 . . C C6 0.37634(15) 0.13462(9) 0.40673(11) 0.0283(3) Uani d 1 . . H H6A 0.306161 0.089483 0.357744 0.034 Uiso calc 1 . . H H6B 0.484451 0.121942 0.394673 0.034 Uiso calc 1 . . C C7 0.36601(15) 0.11332(9) 0.52956(11) 0.0292(3) Uani d 1 . . H H7A 0.391137 0.043785 0.544622 0.035 Uiso calc 1 . . H H7B 0.256606 0.123530 0.540072 0.035 Uiso calc 1 . . C C8 0.47243(15) 0.17420(9) 0.61698(11) 0.0307(3) Uani d 1 . . H H8A 0.582141 0.161925 0.608561 0.037 Uiso calc 1 . . H H8B 0.460131 0.151458 0.692992 0.037 Uiso calc 1 . . C C9 0.44330(14) 0.28469(9) 0.61047(9) 0.0265(2) Uani d 1 . . H H9A 0.329164 0.296497 0.597463 0.032 Uiso calc 1 . . H H9B 0.488083 0.314069 0.684049 0.032 Uiso calc 1 . . C C9A 0.51199(12) 0.33508(8) 0.51922(9) 0.0215(2) Uani d 1 . . O O1 0.79988(9) 0.51505(6) 0.51257(6) 0.02512(18) Uani d 1 . . C C10 0.85462(14) 0.52347(9) 0.63198(9) 0.0274(2) Uani d 1 . . H H10A 0.939489 0.571270 0.645841 0.041 Uiso calc 1 . . H H10B 0.893140 0.460149 0.662292 0.041 Uiso calc 1 . . H H10C 0.768497 0.544735 0.669146 0.041 Uiso calc 1 . . C C11 0.72102(12) 0.49002(8) 0.28838(9) 0.0206(2) Uani d 1 . . N N2 0.78244(11) 0.53879(7) 0.23194(8) 0.0256(2) Uani d 1 . . C C4 0.53379(12) 0.36142(8) 0.32516(9) 0.0191(2) Uani d 1 . . C C12 0.4956(4) 0.3372(2) 0.20351(15) 0.0192(6) Uani d 0.9165(18) A 1 S S1 0.41398(4) 0.42140(3) 0.10427(4) 0.02356(11) Uani d 0.9165(18) A 1 C C13 0.5122(4) 0.2478(2) 0.1561(3) 0.0241(6) Uani d 0.9165(18) A 1 H H13 0.554088 0.192012 0.197180 0.029 Uiso calc 0.9165(18) A 1 C C14 0.45807(17) 0.24944(12) 0.03647(12) 0.0265(3) Uani d 0.9165(18) A 1 H H14 0.461758 0.194492 -0.010884 0.032 Uiso calc 0.9165(18) A 1 C C15 0.40077(16) 0.33795(15) -0.00242(11) 0.0276(3) Uani d 0.9165(18) A 1 H H15 0.358864 0.351468 -0.079069 0.033 Uiso calc 0.9165(18) A 1 S S1' 0.4973(14) 0.2438(9) 0.1354(9) 0.034(3) Uiso d 0.0835(18) A 2 C C12' 0.482(5) 0.349(2) 0.2035(17) 0.021(8) Uiso d 0.0835(18) A 2 C C13' 0.416(4) 0.413(2) 0.128(2) 0.079(13) Uiso d 0.0835(18) A 2 H H13' 0.391857 0.477403 0.148342 0.095 Uiso calc 0.0835(18) A 2 C C14' 0.383(2) 0.3797(15) 0.0179(16) 0.037(5) Uiso d 0.0835(18) A 2 H H14' 0.339750 0.418697 -0.044909 0.044 Uiso calc 0.0835(18) A 2 C C15' 0.421(2) 0.2852(15) 0.0112(14) 0.026(4) Uiso d 0.0835(18) A 2 H H15' 0.404855 0.247901 -0.056219 0.031 Uiso calc 0.0835(18) A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N1 0.0234(4) 0.0247(4) 0.0197(4) 0.0042(4) 0.0047(3) 0.0008(4) C2 0.0206(5) 0.0195(5) 0.0224(5) 0.0034(4) 0.0037(4) -0.0009(4) C3 0.0196(5) 0.0183(5) 0.0208(5) 0.0025(4) 0.0049(4) 0.0014(4) C4A 0.0199(5) 0.0194(5) 0.0219(5) 0.0035(4) 0.0054(4) 0.0034(4) C5 0.0236(5) 0.0246(5) 0.0226(5) -0.0018(4) 0.0063(4) 0.0042(4) C6 0.0339(6) 0.0224(5) 0.0315(6) -0.0015(5) 0.0142(5) 0.0026(5) C7 0.0338(6) 0.0237(5) 0.0326(6) 0.0041(5) 0.0131(5) 0.0094(5) C8 0.0322(6) 0.0322(7) 0.0288(6) 0.0051(5) 0.0082(5) 0.0127(5) C9 0.0292(6) 0.0308(6) 0.0211(5) 0.0019(5) 0.0085(4) 0.0037(4) C9A 0.0221(5) 0.0211(5) 0.0222(5) 0.0051(4) 0.0065(4) 0.0028(4) O1 0.0263(4) 0.0268(4) 0.0215(4) -0.0032(3) 0.0018(3) -0.0030(3) C10 0.0296(6) 0.0291(6) 0.0214(5) 0.0020(5) -0.0016(4) -0.0036(4) C11 0.0204(5) 0.0199(5) 0.0213(5) 0.0005(4) 0.0028(4) -0.0031(4) N2 0.0268(5) 0.0255(5) 0.0252(5) -0.0049(4) 0.0062(4) -0.0012(4) C4 0.0192(5) 0.0184(5) 0.0199(5) 0.0036(4) 0.0041(4) 0.0020(4) C12 0.0189(9) 0.0194(9) 0.0198(9) -0.0013(7) 0.0047(5) 0.0031(5) S1 0.02551(18) 0.02386(17) 0.02084(18) 0.00268(11) 0.00265(12) 0.00618(12) C13 0.0299(11) 0.0250(10) 0.0180(12) -0.0021(6) 0.0058(9) 0.0021(8) C14 0.0302(7) 0.0276(7) 0.0230(7) -0.0086(6) 0.0082(5) -0.0050(6) C15 0.0270(6) 0.0379(10) 0.0176(6) -0.0052(6) 0.0032(5) 0.0014(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 N1 C9A . . 118.04(10) ? N1 C2 O1 . . 120.04(10) ? N1 C2 C3 . . 123.43(10) ? O1 C2 C3 . . 116.52(9) ? C4 C3 C2 . . 118.58(10) ? C4 C3 C11 . . 122.97(10) ? C2 C3 C11 . . 118.46(10) ? C9A C4A C4 . . 117.67(10) ? C9A C4A C5 . . 120.04(9) ? C4 C4A C5 . . 122.27(10) ? C4A C5 C6 . . 114.10(9) ? C4A C5 H5A . . 108.7 ? C6 C5 H5A . . 108.7 ? C4A C5 H5B . . 108.7 ? C6 C5 H5B . . 108.7 ? H5A C5 H5B . . 107.6 ? C7 C6 C5 . . 113.31(10) y C7 C6 H6A . . 108.9 ? C5 C6 H6A . . 108.9 ? C7 C6 H6B . . 108.9 ? C5 C6 H6B . . 108.9 ? H6A C6 H6B . . 107.7 ? C6 C7 C8 . . 115.70(10) y C6 C7 H7A . . 108.4 ? C8 C7 H7A . . 108.4 ? C6 C7 H7B . . 108.4 ? C8 C7 H7B . . 108.4 ? H7A C7 H7B . . 107.4 ? C7 C8 C9 . . 115.55(10) y C7 C8 H8A . . 108.4 ? C9 C8 H8A . . 108.4 ? C7 C8 H8B . . 108.4 ? C9 C8 H8B . . 108.4 ? H8A C8 H8B . . 107.5 ? C9A C9 C8 . . 114.11(9) ? C9A C9 H9A . . 108.7 ? C8 C9 H9A . . 108.7 ? C9A C9 H9B . . 108.7 ? C8 C9 H9B . . 108.7 ? H9A C9 H9B . . 107.6 ? N1 C9A C4A . . 123.66(10) ? N1 C9A C9 . . 115.16(10) y C4A C9A C9 . . 121.18(10) ? C2 O1 C10 . . 116.49(9) ? O1 C10 H10A . . 109.5 ? O1 C10 H10B . . 109.5 ? H10A C10 H10B . . 109.5 ? O1 C10 H10C . . 109.5 ? H10A C10 H10C . . 109.5 ? H10B C10 H10C . . 109.5 ? N2 C11 C3 . . 177.19(12) ? C3 C4 C4A . . 118.54(10) ? C3 C4 C12' . . 119.0(16) ? C4A C4 C12' . . 122.1(16) ? C3 C4 C12 . . 120.25(15) ? C4A C4 C12 . . 121.19(15) ? C13 C12 C4 . . 126.1(2) ? C13 C12 S1 . . 111.88(18) ? C4 C12 S1 . . 121.9(2) ? C15 S1 C12 . . 92.11(10) ? C12 C13 C14 . . 111.3(2) ? C12 C13 H13 . . 124.4 ? C14 C13 H13 . . 124.4 ? C15 C14 C13 . . 113.24(17) ? C15 C14 H14 . . 123.4 ? C13 C14 H14 . . 123.4 ? C14 C15 S1 . . 111.49(10) ? C14 C15 H15 . . 124.3 ? S1 C15 H15 . . 124.3 ? C15' S1' C12' . . 95.4(12) ? C13' C12' C4 . . 129(2) ? C13' C12' S1' . . 107.5(16) ? C4 C12' S1' . . 123.8(18) ? C12' C13' C14' . . 115(2) ? C12' C13' H13' . . 122.3 ? C14' C13' H13' . . 122.3 ? C15' C14' C13' . . 111.4(18) ? C15' C14' H14' . . 124.3 ? C13' C14' H14' . . 124.3 ? C14' C15' S1' . . 110.3(13) ? C14' C15' H15' . . 124.9 ? S1' C15' H15' . . 124.9 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C2 . 1.3212(14) ? N1 C9A . 1.3455(15) ? C2 O1 . 1.3470(13) ? C2 C3 . 1.4035(15) ? C3 C4 . 1.4019(15) ? C3 C11 . 1.4348(14) ? C4A C9A . 1.4043(15) ? C4A C4 . 1.4045(14) ? C4A C5 . 1.5104(15) ? C5 C6 . 1.5358(16) ? C5 H5A . 0.9900 ? C5 H5B . 0.9900 ? C6 C7 . 1.5251(16) ? C6 H6A . 0.9900 ? C6 H6B . 0.9900 ? C7 C8 . 1.5253(19) ? C7 H7A . 0.9900 ? C7 H7B . 0.9900 ? C8 C9 . 1.5393(17) ? C8 H8A . 0.9900 ? C8 H8B . 0.9900 ? C9 C9A . 1.5060(14) ? C9 H9A . 0.9900 ? C9 H9B . 0.9900 ? O1 C10 . 1.4387(13) ? C10 H10A . 0.9800 ? C10 H10B . 0.9800 ? C10 H10C . 0.9800 ? C11 N2 . 1.1490(14) ? C4 C12' . 1.466(19) ? C4 C12 . 1.482(2) ? C12 C13 . 1.373(4) ? C12 S1 . 1.725(3) ? S1 C15 . 1.7109(18) ? C13 C14 . 1.436(3) ? C13 H13 . 0.9500 ? C14 C15 . 1.366(2) ? C14 H14 . 0.9500 ? C15 H15 . 0.9500 ? S1' C15' . 1.630(17) ? S1' C12' . 1.67(2) ? C12' C13' . 1.33(2) ? C13' C14' . 1.39(2) ? C13' H13' . 0.9500 ? C14' C15' . 1.345(19) ? C14' H14' . 0.9500 ? C15' H15' . 0.9500 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C13 H13 N2 2_645 0.95 2.60 3.524(3) 164.3 yes C15 H15 N2 3_665 0.95 2.53 3.3941(19) 151.7 yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C9A N1 C2 O1 . . . . 179.93(9) ? C9A N1 C2 C3 . . . . -1.04(16) ? N1 C2 C3 C4 . . . . -1.29(16) ? O1 C2 C3 C4 . . . . 177.77(9) ? N1 C2 C3 C11 . . . . 178.70(10) ? O1 C2 C3 C11 . . . . -2.24(14) ? C9A C4A C5 C6 . . . . -68.49(13) y C4 C4A C5 C6 . . . . 112.99(11) ? C4A C5 C6 C7 . . . . 81.19(12) y C5 C6 C7 C8 . . . . -60.92(14) y C6 C7 C8 C9 . . . . 61.40(14) y C7 C8 C9 C9A . . . . -78.94(13) y C2 N1 C9A C4A . . . . 1.50(16) ? C2 N1 C9A C9 . . . . -179.26(9) ? C4 C4A C9A N1 . . . . 0.40(15) ? C5 C4A C9A N1 . . . . -178.19(10) ? C4 C4A C9A C9 . . . . -178.79(10) ? C5 C4A C9A C9 . . . . 2.62(15) y C8 C9 C9A N1 . . . . -116.61(11) ? C8 C9 C9A C4A . . . . 62.64(14) y N1 C2 O1 C10 . . . . 5.86(14) ? C3 C2 O1 C10 . . . . -173.24(9) ? C2 C3 C4 C4A . . . . 3.15(15) ? C11 C3 C4 C4A . . . . -176.84(9) ? C2 C3 C4 C12' . . . . 176.0(15) ? C11 C3 C4 C12' . . . . -4.0(15) ? C2 C3 C4 C12 . . . . -175.38(17) ? C11 C3 C4 C12 . . . . 4.6(2) ? C9A C4A C4 C3 . . . . -2.71(14) ? C5 C4A C4 C3 . . . . 175.84(9) ? C9A C4A C4 C12' . . . . -175.4(14) ? C5 C4A C4 C12' . . . . 3.2(14) ? C9A C4A C4 C12 . . . . 175.80(17) ? C5 C4A C4 C12 . . . . -5.6(2) ? C3 C4 C12 C13 . . . . 119.7(3) ? C4A C4 C12 C13 . . . . -58.8(4) ? C3 C4 C12 S1 . . . . -63.4(3) ? C4A C4 C12 S1 . . . . 118.13(19) ? C13 C12 S1 C15 . . . . 0.0(2) ? C4 C12 S1 C15 . . . . -177.3(2) ? C4 C12 C13 C14 . . . . 177.7(3) ? S1 C12 C13 C14 . . . . 0.5(3) ? C12 C13 C14 C15 . . . . -1.0(3) ? C13 C14 C15 S1 . . . . 1.0(2) ? C12 S1 C15 C14 . . . . -0.58(14) ? C3 C4 C12' C13' . . . . -59(3) ? C4A C4 C12' C13' . . . . 113(2) ? C3 C4 C12' S1' . . . . 122(2) ? C4A C4 C12' S1' . . . . -66(3) ? C15' S1' C12' C13' . . . . 1.0(16) ? C15' S1' C12' C4 . . . . -180(3) ? C4 C12' C13' C14' . . . . 179(4) ? S1' C12' C13' C14' . . . . -2(2) ? C12' C13' C14' C15' . . . . 3(3) ? C13' C14' C15' S1' . . . . -2(3) ? C12' S1' C15' C14' . . . . 1(2) ?