#------------------------------------------------------------------------------ #$Date: 2026-06-17 23:23:47 +0100 (Wed, 17 Jun 2026) $ #$Revision: 306587 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/74/1577408.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1577408 loop_ _publ_author_name 'Wang, Haiwen' 'Bhaduri, Nilanjan' 'Greaney, Michael F.' _publ_section_title ; Trifluoromethylation of pyridines through skeletal rearrangement ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D6SC04438G _journal_year 2026 _chemical_formula_moiety 'C13 H9 N O3' _chemical_formula_sum 'C13 H9 N O3' _chemical_formula_weight 227.21 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2025-09-01 _audit_creation_method ; Olex2 1.5 (compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314) ; _audit_update_record ; 2025-09-11 deposited with the CCDC. 2026-06-08 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 111.530(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.07570(10) _cell_length_b 24.4204(5) _cell_length_c 7.3631(2) _cell_measurement_reflns_used 3778 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 75.3850 _cell_measurement_theta_min 7.2040 _cell_volume 1016.24(4) _computing_cell_refinement 'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)' _computing_data_collection 'CrysAlisPro system (CCD 44.117a 64-bit (release 07-07-2025))' _computing_data_reduction 'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2019/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.00(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.951 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -6.00 70.00 0.50 0.17 -- 43.52 10.00-150.00 152 2 \w 79.00 128.00 0.50 0.17 -- 43.52 10.00-150.00 98 3 \w -37.00 3.00 0.50 0.17 -- 46.08 10.00 0.00 80 4 \w 83.00 135.00 0.50 0.17 -- 46.08 10.00 0.00 104 5 \w 47.00 73.00 0.50 0.17 -- 46.08 10.00 0.00 52 6 \w 19.00 45.00 0.50 0.17 -- 108.20 50.00 0.00 52 7 \w 117.00 143.00 0.50 0.17 -- 108.20 0.00 -90.00 52 8 \w 20.00 91.00 0.50 0.17 -- 108.20 60.00 60.00 142 9 \w 24.00 113.00 0.50 0.17 -- 108.20 0.00 -90.00 178 10 \w 83.00 198.00 0.50 0.17 -- 108.20 50.00 0.00 230 11 \w 55.00 81.00 0.50 0.17 -- 108.20 40.00-150.00 52 12 \w 95.00 123.00 0.50 0.17 -- 108.20 40.00-150.00 56 13 \w 143.00 197.00 0.50 0.17 -- 108.20 40.00-150.00 108 14 \w 173.00 198.00 0.50 0.17 -- 108.20 0.00 0.00 50 15 \w 141.00 198.00 0.50 0.17 -- 108.20 60.00 60.00 114 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB AFC11 (RINC): quarter-chi single' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.2296020000 _diffrn_orient_matrix_UB_12 0.0335219000 _diffrn_orient_matrix_UB_13 0.0882329000 _diffrn_orient_matrix_UB_21 -0.0922210000 _diffrn_orient_matrix_UB_22 0.0248123000 _diffrn_orient_matrix_UB_23 0.1509618000 _diffrn_orient_matrix_UB_31 0.1143118000 _diffrn_orient_matrix_UB_32 -0.0473347000 _diffrn_orient_matrix_UB_33 0.1415284000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_unetI/netI 0.0331 _diffrn_reflns_Laue_measured_fraction_full 0.992 _diffrn_reflns_Laue_measured_fraction_max 0.951 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 5061 _diffrn_reflns_point_group_measured_fraction_full 0.788 _diffrn_reflns_point_group_measured_fraction_max 0.742 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.177 _diffrn_reflns_theta_min 6.463 _diffrn_source 'Rotating-anode X-ray tube (dual wavelength)' _diffrn_source_type 'Rigaku (Cu) X-ray DW Source' _exptl_absorpt_coefficient_mu 0.889 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.655 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.43.112a (Rigaku Oxford Diffraction, 2024) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.485 _exptl_crystal_description block _exptl_crystal_F_000 472 _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.196 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.038 _refine_ls_abs_structure_details ; Flack x determined using 1020 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.00(12) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 315 _refine_ls_number_reflns 3162 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.063 _refine_ls_R_factor_all 0.0296 _refine_ls_R_factor_gt 0.0288 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0456P)^2^+0.1339P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0788 _refine_ls_wR_factor_ref 0.0794 _reflns_Friedel_coverage 0.522 _reflns_Friedel_fraction_full 0.572 _reflns_Friedel_fraction_max 0.522 _reflns_number_gt 3073 _reflns_number_total 3162 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc04438g2.cif _cod_data_source_block s6747l _cod_database_code 1577408 _shelx_shelxl_version_number 2019/3 _chemical_oxdiff_formula C13H9NO3 _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_max 0.940 _shelx_estimated_absorpt_t_min 0.871 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C9A(H9A), C4H(H4H), C11H(H11H), C3H(H3H), C10A(H10A), C5H(H5H), C5A(H5A), C11A(H11A), C10H(H10H), C1H(H1HA), C1A(H1A), C2A(H2A), C2H(H2H), C9H(H9H), C3A(H3AA), C4A(H4A) ; _shelx_res_file ; TITL s6747l_a.res in P2(1) s6747l.res created by SHELXL-2019/3 at 11:12:41 on 01-Sep-2025 REM Old TITL s6747l in P21/m #11 REM SHELXT solution in P2(1): R1 0.071, Rweak 0.013, Alpha 0.011 REM 0.761 for 14 systematic absences, Orientation as input REM Flack x = 0.147 ( 0.101 ) from 1028 Parsons' quotients REM Formula found by SHELXT: C27 N O6 CELL 1.54184 6.0757 24.4204 7.3631 90 111.53 90 ZERR 4 0.0001 0.0005 0.0002 0 0.003 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N O UNIT 52 36 4 12 EQIV $1 +X,+Y,-1+Z L.S. 14 PLAN 25 SIZE 0.07 0.14 0.16 TEMP -173 CONF FREE O3H H3A_$1 BOND list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.045600 0.133900 FVAR 1.51379 O2A 4 0.507128 0.400181 0.611188 11.00000 0.02891 0.01968 = 0.01747 0.00302 0.00895 0.00388 O1H 4 0.099461 0.586325 0.089686 11.00000 0.01949 0.02230 = 0.02403 -0.00136 0.00470 -0.00338 O3H 4 0.583322 0.508110 -0.077674 11.00000 0.02033 0.02069 = 0.01862 -0.00407 0.00488 0.00296 O3A 4 0.405969 0.489309 0.563493 11.00000 0.02194 0.01524 = 0.02007 -0.00353 0.00568 0.00107 O2H 4 0.437978 0.593979 -0.124696 11.00000 0.03914 0.02322 = 0.01906 0.00320 0.01001 0.01097 O1A 4 0.870285 0.412792 0.425414 11.00000 0.01764 0.01910 = 0.02104 -0.00198 0.00490 -0.00143 N1H 3 0.822425 0.535425 0.306261 11.00000 0.01803 0.01392 = 0.02033 -0.00176 0.00803 -0.00017 C12H 1 0.621890 0.560995 0.196519 11.00000 0.01540 0.01129 = 0.02088 0.00093 0.00525 -0.00130 N1A 3 0.138668 0.458348 0.179447 11.00000 0.01706 0.01652 = 0.01772 0.00154 0.00612 0.00102 C9A 1 0.389029 0.394353 0.005793 11.00000 0.02114 0.01681 = 0.01711 -0.00258 0.00775 -0.00115 AFIX 43 H9A 2 0.474371 0.372826 -0.053557 11.00000 -1.20000 AFIX 0 C7H 1 0.262418 0.617037 0.174338 11.00000 0.01710 0.01957 = 0.01338 -0.00034 0.00644 -0.00041 C13A 1 0.427241 0.439607 0.505787 11.00000 0.01344 0.01563 = 0.01957 -0.00006 0.00703 0.00031 C8H 1 0.504440 0.593329 0.287290 11.00000 0.01678 0.01425 = 0.01898 -0.00031 0.00709 -0.00077 C6A 1 0.764513 0.321799 0.315604 11.00000 0.01853 0.01782 = 0.01450 0.00038 0.00741 0.00162 C4H 1 0.387616 0.768639 0.247863 11.00000 0.02485 0.01953 = 0.02184 0.00028 0.00807 -0.00004 AFIX 43 H4H 2 0.518600 0.792988 0.283498 11.00000 -1.20000 AFIX 0 C8A 1 0.476332 0.402134 0.207022 11.00000 0.01753 0.01349 = 0.01653 0.00104 0.00536 -0.00149 C6H 1 0.230320 0.676930 0.185298 11.00000 0.01831 0.01805 = 0.01519 0.00105 0.00646 0.00143 C11H 1 0.921152 0.541151 0.501213 11.00000 0.01786 0.01925 = 0.01886 0.00413 0.00408 0.00187 AFIX 43 H11H 2 1.065154 0.522912 0.572564 11.00000 -1.20000 AFIX 0 C13H 1 0.537344 0.554541 -0.024659 11.00000 0.01732 0.01924 = 0.01662 -0.00149 0.00694 0.00031 C3H 1 0.160899 0.788943 0.202141 11.00000 0.03091 0.01727 = 0.02107 0.00175 0.00850 0.00655 AFIX 43 H3H 2 0.136986 0.827228 0.208578 11.00000 -1.20000 AFIX 0 C10A 1 0.176755 0.418319 -0.106575 11.00000 0.02028 0.01917 = 0.01613 -0.00019 0.00540 -0.00202 AFIX 43 H10A 2 0.112738 0.413293 -0.244089 11.00000 -1.20000 AFIX 0 C5H 1 0.423258 0.712566 0.241539 11.00000 0.01786 0.02011 = 0.01887 0.00154 0.00683 0.00269 AFIX 43 H5H 2 0.579026 0.698499 0.275517 11.00000 -1.20000 AFIX 0 C5A 1 0.580073 0.284071 0.259927 11.00000 0.01777 0.02107 = 0.02071 0.00032 0.00670 0.00142 AFIX 43 H5A 2 0.421817 0.296319 0.227504 11.00000 -1.20000 AFIX 0 C11A 1 0.059026 0.449892 -0.014286 11.00000 0.01622 0.02043 = 0.01835 0.00042 0.00348 0.00066 AFIX 43 H11A 2 -0.086279 0.466489 -0.092591 11.00000 -1.20000 AFIX 0 C10H 1 0.812864 0.573573 0.597396 11.00000 0.02037 0.01945 = 0.01649 0.00017 0.00502 -0.00191 AFIX 43 H10H 2 0.882083 0.578288 0.734887 11.00000 -1.20000 AFIX 0 C1H 1 0.002366 0.697637 0.136662 11.00000 0.01776 0.02210 = 0.02161 0.00110 0.00686 0.00051 AFIX 43 H1HA 2 -0.129559 0.673530 0.096553 11.00000 -1.20000 AFIX 0 C1A 1 0.998612 0.303602 0.364687 11.00000 0.01698 0.02190 = 0.02053 0.00076 0.00673 0.00089 AFIX 43 H1A 2 1.125930 0.328998 0.404414 11.00000 -1.20000 AFIX 0 C2A 1 1.041620 0.248224 0.354491 11.00000 0.01899 0.02420 = 0.02419 0.00449 0.00776 0.00685 AFIX 43 H2A 2 1.199469 0.235748 0.386348 11.00000 -1.20000 AFIX 0 C7A 1 0.717393 0.381146 0.328484 11.00000 0.01597 0.01861 = 0.01530 0.00077 0.00760 0.00020 C2H 1 -0.031785 0.753670 0.146919 11.00000 0.02070 0.02585 = 0.02448 0.00063 0.00894 0.00784 AFIX 43 H2H 2 -0.186915 0.767828 0.116154 11.00000 -1.20000 AFIX 0 C12A 1 0.342248 0.433989 0.287103 11.00000 0.01738 0.01259 = 0.01696 0.00006 0.00693 -0.00141 C9H 1 0.600750 0.599223 0.489685 11.00000 0.01767 0.01741 = 0.02016 0.00068 0.00830 -0.00070 AFIX 43 H9H 2 0.521328 0.620789 0.554032 11.00000 -1.20000 AFIX 0 C3A 1 0.857600 0.210785 0.298475 11.00000 0.02726 0.01772 = 0.02208 0.00091 0.00951 0.00424 AFIX 43 H3AA 2 0.889844 0.172912 0.292208 11.00000 -1.20000 AFIX 0 C4A 1 0.626054 0.228475 0.251446 11.00000 0.02379 0.01896 = 0.02339 0.00028 0.00684 -0.00282 AFIX 43 H4A 2 0.499789 0.202796 0.213714 11.00000 -1.20000 AFIX 0 H3A 2 0.486512 0.491557 0.718688 11.00000 0.07223 H1H 2 0.901629 0.513315 0.252619 11.00000 0.03979 HKLF 4 REM s6747l_a.res in P2(1) REM wR2 = 0.0794, GooF = S = 1.063, Restrained GooF = 1.063 for all data REM R1 = 0.0288 for 3073 Fo > 4sig(Fo) and 0.0296 for all 3162 data REM 315 parameters refined using 1 restraints END WGHT 0.0456 0.1338 REM Highest difference peak 0.196, deepest hole -0.202, 1-sigma level 0.038 Q1 1 0.5821 0.5587 0.0965 11.00000 0.05 0.20 Q2 1 0.3933 0.4407 0.3837 11.00000 0.05 0.19 Q3 1 0.7473 0.2222 0.2765 11.00000 0.05 0.18 Q4 1 0.3948 0.6059 0.2445 11.00000 0.05 0.18 Q5 1 0.4093 0.4171 0.2608 11.00000 0.05 0.17 Q6 1 0.8625 0.3195 0.3219 11.00000 0.05 0.17 Q7 1 0.4306 0.4010 0.1203 11.00000 0.05 0.16 Q8 1 0.5967 0.3923 0.2511 11.00000 0.05 0.16 Q9 1 0.1370 0.6807 0.1806 11.00000 0.05 0.16 Q10 1 0.6768 0.5821 0.5472 11.00000 0.05 0.15 Q11 1 0.5709 0.5832 0.2395 11.00000 0.05 0.15 Q12 1 0.2578 0.7767 0.2183 11.00000 0.05 0.15 Q13 1 0.5624 0.5961 0.3750 11.00000 0.05 0.14 Q14 1 0.6769 0.3024 0.2689 11.00000 0.05 0.14 Q15 1 0.3187 0.4169 -0.0474 11.00000 0.05 0.14 Q16 1 0.2689 0.6494 0.1748 11.00000 0.05 0.14 Q17 1 0.7223 0.5340 -0.0214 11.00000 0.05 0.13 Q18 1 0.7440 0.3464 0.3067 11.00000 0.05 0.13 Q19 1 0.9369 0.2261 0.3878 11.00000 0.05 0.13 Q20 1 0.1534 0.5399 0.1978 11.00000 0.05 0.13 Q21 1 0.2652 0.4667 0.5250 11.00000 0.05 0.13 Q22 1 0.5985 0.4796 0.0431 11.00000 0.05 0.12 Q23 1 0.8558 0.4600 0.3162 11.00000 0.05 0.12 Q24 1 0.6195 0.4992 0.4327 11.00000 0.05 0.12 Q25 1 0.3148 0.6976 0.2260 11.00000 0.05 0.12 ; _shelx_res_checksum 83618 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.406 _oxdiff_exptl_absorpt_empirical_full_min 0.815 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O2A O 0.5071(3) 0.40018(7) 0.6112(2) 0.0219(4) Uani 1 1 d . . . . . O1H O 0.0995(3) 0.58633(8) 0.0897(2) 0.0229(4) Uani 1 1 d . . . . . O3H O 0.5833(3) 0.50811(7) -0.0777(2) 0.0205(4) Uani 1 1 d . . . . . O3A O 0.4060(3) 0.48931(7) 0.5635(2) 0.0197(4) Uani 1 1 d . . . . . O2H O 0.4380(3) 0.59398(8) -0.1247(2) 0.0273(4) Uani 1 1 d . . . . . O1A O 0.8703(3) 0.41279(7) 0.4254(2) 0.0199(4) Uani 1 1 d . . . . . N1H N 0.8224(3) 0.53542(8) 0.3063(3) 0.0171(4) Uani 1 1 d . . . . . C12H C 0.6219(4) 0.56099(10) 0.1965(3) 0.0163(4) Uani 1 1 d . . . . . N1A N 0.1387(3) 0.45835(9) 0.1794(3) 0.0172(4) Uani 1 1 d . . . . . C9A C 0.3890(4) 0.39435(10) 0.0058(3) 0.0181(5) Uani 1 1 d . . . . . H9A H 0.474371 0.372826 -0.053557 0.022 Uiso 1 1 calc R U . . . C7H C 0.2624(4) 0.61704(10) 0.1743(3) 0.0164(5) Uani 1 1 d . . . . . C13A C 0.4272(4) 0.43961(10) 0.5058(3) 0.0159(4) Uani 1 1 d . . . . . C8H C 0.5044(4) 0.59333(10) 0.2873(3) 0.0165(4) Uani 1 1 d . . . . . C6A C 0.7645(4) 0.32180(10) 0.3156(3) 0.0166(5) Uani 1 1 d . . . . . C4H C 0.3876(4) 0.76864(10) 0.2479(3) 0.0222(5) Uani 1 1 d . . . . . H4H H 0.518600 0.792988 0.283498 0.027 Uiso 1 1 calc R U . . . C8A C 0.4763(4) 0.40213(9) 0.2070(3) 0.0161(5) Uani 1 1 d . . . . . C6H C 0.2303(4) 0.67693(10) 0.1853(3) 0.0171(5) Uani 1 1 d . . . . . C11H C 0.9212(4) 0.54115(11) 0.5012(3) 0.0194(5) Uani 1 1 d . . . . . H11H H 1.065154 0.522912 0.572564 0.023 Uiso 1 1 calc R U . . . C13H C 0.5373(4) 0.55454(10) -0.0247(3) 0.0175(5) Uani 1 1 d . . . . . C3H C 0.1609(4) 0.78894(11) 0.2021(3) 0.0234(5) Uani 1 1 d . . . . . H3H H 0.136986 0.827228 0.208578 0.028 Uiso 1 1 calc R U . . . C10A C 0.1768(4) 0.41832(10) -0.1066(3) 0.0189(5) Uani 1 1 d . . . . . H10A H 0.112738 0.413293 -0.244089 0.023 Uiso 1 1 calc R U . . . C5H C 0.4233(4) 0.71257(10) 0.2415(3) 0.0189(5) Uani 1 1 d . . . . . H5H H 0.579026 0.698499 0.275517 0.023 Uiso 1 1 calc R U . . . C5A C 0.5801(4) 0.28407(11) 0.2599(3) 0.0200(5) Uani 1 1 d . . . . . H5A H 0.421817 0.296319 0.227504 0.024 Uiso 1 1 calc R U . . . C11A C 0.0590(4) 0.44989(10) -0.0143(3) 0.0191(5) Uani 1 1 d . . . . . H11A H -0.086279 0.466489 -0.092591 0.023 Uiso 1 1 calc R U . . . C10H C 0.8129(4) 0.57357(10) 0.5974(4) 0.0193(5) Uani 1 1 d . . . . . H10H H 0.882083 0.578288 0.734887 0.023 Uiso 1 1 calc R U . . . C1H C 0.0024(4) 0.69764(11) 0.1367(4) 0.0206(5) Uani 1 1 d . . . . . H1HA H -0.129559 0.673530 0.096553 0.025 Uiso 1 1 calc R U . . . C1A C 0.9986(4) 0.30360(11) 0.3647(3) 0.0198(5) Uani 1 1 d . . . . . H1A H 1.125930 0.328998 0.404414 0.024 Uiso 1 1 calc R U . . . C2A C 1.0416(4) 0.24822(12) 0.3545(4) 0.0225(5) Uani 1 1 d . . . . . H2A H 1.199469 0.235748 0.386348 0.027 Uiso 1 1 calc R U . . . C7A C 0.7174(4) 0.38115(10) 0.3285(3) 0.0161(5) Uani 1 1 d . . . . . C2H C -0.0318(4) 0.75367(12) 0.1469(4) 0.0235(5) Uani 1 1 d . . . . . H2H H -0.186915 0.767828 0.116154 0.028 Uiso 1 1 calc R U . . . C12A C 0.3422(4) 0.43399(10) 0.2871(3) 0.0155(4) Uani 1 1 d . . . . . C9H C 0.6008(4) 0.59922(10) 0.4897(3) 0.0180(5) Uani 1 1 d . . . . . H9H H 0.521328 0.620789 0.554032 0.022 Uiso 1 1 calc R U . . . C3A C 0.8576(4) 0.21078(11) 0.2985(4) 0.0222(5) Uani 1 1 d . . . . . H3AA H 0.889844 0.172912 0.292208 0.027 Uiso 1 1 calc R U . . . C4A C 0.6261(4) 0.22847(10) 0.2514(4) 0.0226(5) Uani 1 1 d . . . . . H4A H 0.499789 0.202796 0.213714 0.027 Uiso 1 1 calc R U . . . H3A H 0.487(8) 0.4916(19) 0.719(7) 0.072(12) Uiso 1 1 d . . . . . H1H H 0.902(6) 0.5133(14) 0.253(5) 0.040(8) Uiso 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2A 0.0289(9) 0.0197(9) 0.0175(8) 0.0030(6) 0.0090(6) 0.0039(7) O1H 0.0195(8) 0.0223(10) 0.0240(8) -0.0014(7) 0.0047(6) -0.0034(7) O3H 0.0203(7) 0.0207(9) 0.0186(8) -0.0041(6) 0.0049(6) 0.0030(7) O3A 0.0219(8) 0.0152(9) 0.0201(8) -0.0035(6) 0.0057(6) 0.0011(6) O2H 0.0391(10) 0.0232(10) 0.0191(8) 0.0032(7) 0.0100(7) 0.0110(8) O1A 0.0176(7) 0.0191(9) 0.0210(8) -0.0020(7) 0.0049(6) -0.0014(6) N1H 0.0180(9) 0.0139(10) 0.0203(10) -0.0018(8) 0.0080(7) -0.0002(8) C12H 0.0154(9) 0.0113(11) 0.0209(11) 0.0009(8) 0.0052(8) -0.0013(8) N1A 0.0171(8) 0.0165(10) 0.0177(10) 0.0015(7) 0.0061(7) 0.0010(7) C9A 0.0211(11) 0.0168(12) 0.0171(11) -0.0026(9) 0.0078(8) -0.0012(9) C7H 0.0171(10) 0.0196(11) 0.0134(11) -0.0003(8) 0.0064(8) -0.0004(9) C13A 0.0134(9) 0.0156(11) 0.0196(11) -0.0001(9) 0.0070(8) 0.0003(8) C8H 0.0168(10) 0.0142(11) 0.0190(10) -0.0003(10) 0.0071(8) -0.0008(9) C6A 0.0185(10) 0.0178(12) 0.0145(11) 0.0004(8) 0.0074(8) 0.0016(9) C4H 0.0248(12) 0.0195(13) 0.0218(13) 0.0003(10) 0.0081(10) 0.0000(10) C8A 0.0175(10) 0.0135(11) 0.0165(11) 0.0010(9) 0.0054(8) -0.0015(9) C6H 0.0183(10) 0.0181(12) 0.0152(11) 0.0011(9) 0.0065(8) 0.0014(9) C11H 0.0179(10) 0.0193(13) 0.0189(12) 0.0041(9) 0.0041(9) 0.0019(9) C13H 0.0173(10) 0.0192(12) 0.0166(11) -0.0015(9) 0.0069(8) 0.0003(9) C3H 0.0309(13) 0.0173(12) 0.0211(12) 0.0017(10) 0.0085(10) 0.0066(10) C10A 0.0203(10) 0.0192(13) 0.0161(10) -0.0002(9) 0.0054(8) -0.0020(9) C5H 0.0179(10) 0.0201(13) 0.0189(12) 0.0015(9) 0.0068(9) 0.0027(9) C5A 0.0178(10) 0.0211(13) 0.0207(12) 0.0003(10) 0.0067(9) 0.0014(9) C11A 0.0162(10) 0.0204(13) 0.0183(11) 0.0004(9) 0.0035(9) 0.0007(9) C10H 0.0204(11) 0.0194(13) 0.0165(10) 0.0002(8) 0.0050(9) -0.0019(9) C1H 0.0178(11) 0.0221(13) 0.0216(11) 0.0011(9) 0.0069(9) 0.0005(9) C1A 0.0170(10) 0.0219(13) 0.0205(11) 0.0008(9) 0.0067(9) 0.0009(9) C2A 0.0190(10) 0.0242(13) 0.0242(12) 0.0045(10) 0.0078(9) 0.0069(9) C7A 0.0160(10) 0.0186(11) 0.0153(11) 0.0008(9) 0.0076(8) 0.0002(9) C2H 0.0207(10) 0.0259(14) 0.0245(12) 0.0006(10) 0.0089(9) 0.0078(10) C12A 0.0174(10) 0.0126(11) 0.0170(11) 0.0001(9) 0.0069(8) -0.0014(8) C9H 0.0177(10) 0.0174(12) 0.0202(11) 0.0007(9) 0.0083(8) -0.0007(9) C3A 0.0273(12) 0.0177(12) 0.0221(12) 0.0009(9) 0.0095(10) 0.0042(10) C4A 0.0238(11) 0.0190(13) 0.0234(12) 0.0003(10) 0.0068(9) -0.0028(10) 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' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 2 -4 0.0719 0 -1 4 0.0438 -1 15 0 0.0596 1 -15 -1 0.0797 1 -11 -3 0.0843 1 -10 3 0.0777 4 6 -3 0.0150 -3 -7 3 0.0426 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13H O3H H3A 121.1(19) . 1_554 ? C13A O3A H3A 110(2) . . ? C12H N1H C11H 123.0(2) . . ? C12H N1H H1H 122(2) . . ? C11H N1H H1H 115(2) . . ? N1H C12H C8H 119.2(2) . . ? N1H C12H C13H 118.0(2) . . ? C8H C12H C13H 122.8(2) . . ? C12A N1A C11A 117.05(19) . . ? C8A C9A H9A 120.4 . . ? C10A C9A H9A 120.4 . . ? C10A C9A C8A 119.2(2) . . ? O1H C7H C8H 119.3(2) . . ? O1H C7H C6H 122.6(2) . . ? C6H C7H C8H 117.9(2) . . ? O2A C13A O3A 126.1(2) . . ? O2A C13A C12A 120.6(2) . . ? O3A C13A C12A 113.32(19) . . ? C12H C8H C7H 121.3(2) . . ? C12H C8H C9H 119.0(2) . . ? C9H C8H C7H 119.33(19) . . ? C5A C6A C1A 119.8(2) . . ? C5A C6A C7A 120.7(2) . . ? C1A C6A C7A 119.5(2) . . ? C3H C4H H4H 120.1 . . ? C3H C4H C5H 119.9(2) . . ? C5H C4H H4H 120.1 . . ? C9A C8A C7A 119.7(2) . . ? C9A C8A C12A 118.0(2) . . ? C12A C8A C7A 122.0(2) . . ? C5H C6H C7H 121.3(2) . . ? C1H C6H C7H 118.9(2) . . ? C1H C6H C5H 119.9(2) . . ? N1H C11H H11H 120.1 . . ? N1H C11H C10H 119.9(2) . . ? C10H C11H H11H 120.1 . . ? O3H C13H C12H 113.4(2) . . ? O2H C13H O3H 129.4(2) . . ? O2H C13H C12H 117.3(2) . . ? C4H C3H H3H 119.8 . . ? C4H C3H C2H 120.4(3) . . ? C2H C3H H3H 119.8 . . ? C9A C10A H10A 120.7 . . ? C9A C10A C11A 118.6(2) . . ? C11A C10A H10A 120.7 . . ? C4H C5H C6H 120.0(2) . . ? C4H C5H H5H 120.0 . . ? C6H C5H H5H 120.0 . . ? C6A C5A H5A 119.8 . . ? C6A C5A C4A 120.4(2) . . ? C4A C5A H5A 119.8 . . ? N1A C11A C10A 123.8(2) . . ? N1A C11A H11A 118.1 . . ? C10A C11A H11A 118.1 . . ? C11H C10H H10H 120.6 . . ? C11H C10H C9H 118.9(2) . . ? C9H C10H H10H 120.6 . . ? C6H C1H H1HA 120.1 . . ? C2H C1H C6H 119.9(2) . . ? C2H C1H H1HA 120.1 . . ? C6A C1A H1A 120.4 . . ? C2A C1A C6A 119.2(2) . . ? C2A C1A H1A 120.4 . . ? C1A C2A H2A 119.6 . . ? C1A C2A C3A 120.9(2) . . ? C3A C2A H2A 119.6 . . ? O1A C7A C6A 122.2(2) . . ? O1A C7A C8A 120.1(2) . . ? C6A C7A C8A 117.7(2) . . ? C3H C2H C1H 120.0(2) . . ? C3H C2H H2H 120.0 . . ? C1H C2H H2H 120.0 . . ? N1A C12A C13A 118.19(19) . . ? N1A C12A C8A 123.4(2) . . ? C8A C12A C13A 118.4(2) . . ? C8H C9H H9H 120.0 . . ? C10H C9H C8H 120.1(2) . . ? C10H C9H H9H 120.0 . . ? C2A C3A H3AA 119.9 . . ? C2A C3A C4A 120.1(3) . . ? C4A C3A H3AA 119.9 . . ? C5A C4A H4A 120.2 . . ? C3A C4A C5A 119.6(2) . . ? C3A C4A H4A 120.2 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2A C13A 1.220(3) . ? O1H C7H 1.216(3) . ? O3H C13H 1.263(3) . ? O3H H3A 1.45(4) 1_554 ? O3A C13A 1.308(3) . ? O3A H3A 1.07(4) . ? O2H C13H 1.228(3) . ? O1A C7A 1.218(3) . ? N1H C12H 1.343(3) . ? N1H C11H 1.345(3) . ? N1H H1H 0.90(3) . ? C12H C8H 1.389(3) . ? C12H C13H 1.525(3) . ? N1A C11A 1.344(3) . ? N1A C12A 1.339(3) . ? C9A H9A 0.9500 . ? C9A C8A 1.391(3) . ? C9A C10A 1.381(3) . ? C7H C8H 1.514(3) . ? C7H C6H 1.482(3) . ? C13A C12A 1.506(3) . ? C8H C9H 1.394(3) . ? C6A C5A 1.391(3) . ? C6A C1A 1.405(3) . ? C6A C7A 1.487(3) . ? C4H H4H 0.9500 . ? C4H C3H 1.384(4) . ? C4H C5H 1.390(4) . ? C8A C7A 1.499(3) . ? C8A C12A 1.403(3) . ? C6H C5H 1.395(3) . ? C6H C1H 1.392(3) . ? C11H H11H 0.9500 . ? C11H C10H 1.380(3) . ? C3H H3H 0.9500 . ? C3H C2H 1.389(4) . ? C10A H10A 0.9500 . ? C10A C11A 1.387(3) . ? C5H H5H 0.9500 . ? C5A H5A 0.9500 . ? C5A C4A 1.392(4) . ? C11A H11A 0.9500 . ? C10H H10H 0.9500 . ? C10H C9H 1.390(3) . ? C1H H1HA 0.9500 . ? C1H C2H 1.390(4) . ? C1A H1A 0.9500 . ? C1A C2A 1.385(4) . ? C2A H2A 0.9500 . ? C2A C3A 1.385(4) . ? C2H H2H 0.9500 . ? C9H H9H 0.9500 . ? C3A H3AA 0.9500 . ? C3A C4A 1.389(4) . ? C4A H4A 0.9500 . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2A C13A C12A N1A 136.7(2) . . . . ? O2A C13A C12A C8A -41.3(3) . . . . ? O1H C7H C8H C12H 58.7(3) . . . . ? O1H C7H C8H C9H -114.5(3) . . . . ? O1H C7H C6H C5H -164.7(2) . . . . ? O1H C7H C6H C1H 14.7(3) . . . . ? O3A C13A C12A N1A -43.5(3) . . . . ? O3A C13A C12A C8A 138.4(2) . . . . ? N1H C12H C8H C7H -172.0(2) . . . . ? N1H C12H C8H C9H 1.3(3) . . . . ? N1H C12H C13H O3H 33.9(3) . . . . ? N1H C12H C13H O2H -145.6(2) . . . . ? N1H C11H C10H C9H 0.8(4) . . . . ? C12H N1H C11H C10H 1.4(4) . . . . ? C12H C8H C9H C10H 0.9(4) . . . . ? C9A C8A C7A O1A 119.8(3) . . . . ? C9A C8A C7A C6A -56.5(3) . . . . ? C9A C8A C12A N1A -1.8(3) . . . . ? C9A C8A C12A C13A 176.1(2) . . . . ? C9A C10A C11A N1A -0.5(4) . . . . ? C7H C8H C9H C10H 174.3(2) . . . . ? C7H C6H C5H C4H 179.1(2) . . . . ? C7H C6H C1H C2H 179.7(2) . . . . ? C8H C12H C13H O3H -148.1(2) . . . . ? C8H C12H C13H O2H 32.3(3) . . . . ? C8H C7H C6H C5H 20.3(3) . . . . ? C8H C7H C6H C1H -160.2(2) . . . . ? C6A C5A C4A C3A -0.2(4) . . . . ? C6A C1A C2A C3A -0.6(4) . . . . ? C4H C3H C2H C1H -0.2(4) . . . . ? C8A C9A C10A C11A 0.6(4) . . . . ? C6H C7H C8H C12H -126.1(2) . . . . ? C6H C7H C8H C9H 60.7(3) . . . . ? C6H C1H C2H C3H 1.2(4) . . . . ? C11H N1H C12H C8H -2.5(3) . . . . ? C11H N1H C12H C13H 175.6(2) . . . . ? C11H C10H C9H C8H -1.9(4) . . . . ? C13H C12H C8H C7H 10.1(4) . . . . ? C13H C12H C8H C9H -176.7(2) . . . . ? C3H C4H C5H C6H 1.3(4) . . . . ? C10A C9A C8A C7A -173.9(2) . . . . ? C10A C9A C8A C12A 0.4(3) . . . . ? C5H C4H C3H C2H -1.0(4) . . . . ? C5H C6H C1H C2H -0.9(4) . . . . ? C5A C6A C1A C2A 0.8(4) . . . . ? C5A C6A C7A O1A 159.1(2) . . . . ? C5A C6A C7A C8A -24.7(3) . . . . ? C11A N1A C12A C13A -175.9(2) . . . . ? C11A N1A C12A C8A 2.0(3) . . . . ? C1H C6H C5H C4H -0.4(4) . . . . ? C1A C6A C5A C4A -0.4(4) . . . . ? C1A C6A C7A O1A -19.4(3) . . . . ? C1A C6A C7A C8A 156.8(2) . . . . ? C1A C2A C3A C4A 0.0(4) . . . . ? C2A C3A C4A C5A 0.4(4) . . . . ? C7A C6A C5A C4A -178.9(2) . . . . ? C7A C6A C1A C2A 179.3(2) . . . . ? C7A C8A C12A N1A 172.4(2) . . . . ? C7A C8A C12A C13A -9.7(3) . . . . ? C12A N1A C11A C10A -0.8(4) . . . . ? C12A C8A C7A O1A -54.4(3) . . . . ? C12A C8A C7A C6A 129.3(2) . . . . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -0.1275 1.5680 -4.3646 -0.3618 -0.6082 -0.7065 0.0684 -0.6703 4.4103 0.3824 0.6429 0.6637 -1.0110 15.3152 0.3347 0.3108 0.5238 -0.7931 1.0065 -15.2830 -0.7656 -0.3488 -0.5876 0.7301 0.7172 -11.1239 -3.3799 -0.5064 -0.8524 0.1302 0.6694 -9.8664 3.0993 0.0964 0.1613 0.9822 3.5464 5.8332 -2.6341 0.7774 -0.5800 -0.2435 -3.3112 -7.1057 2.8410 -0.7478 0.5579 0.3599