#------------------------------------------------------------------------------ #$Date: 2026-06-19 00:15:13 +0100 (Fri, 19 Jun 2026) $ #$Revision: 306597 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/74/1577420.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_1577420 loop_ _publ_author_name 'Gong, Yanxiang' 'Jia, Yiran' 'Yang, Jie' 'Zhang, Jun' 'Xia, Meng' 'Wang, Xi-Yang' 'Wang, Yunsheng' 'Tao, Ying' 'Fang, Manman' 'Yang, Quan-Hong' 'Zhong Tang, Ben' 'Li, Zhen' _publ_section_title ; Inhibition of shuttle effect in organic cathode and in situ mechanistic exploration ; _journal_name_full 'Energy & Environmental Science' _journal_paper_doi 10.1039/D6EE00605A _journal_year 2026 _chemical_formula_moiety 'C43 H36 N2 O' _chemical_formula_sum 'C43 H36 N2 O' _chemical_formula_weight 596.74 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _audit_block_doi 10.5517/ccdc.csd.cc2np7cz _audit_creation_date 2023-10-07 _audit_creation_method ; Olex2 1.5 (compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817) ; _audit_update_record ; 2025-06-10 deposited with the CCDC. 2026-06-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.784(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.9752(6) _cell_length_b 12.2740(6) _cell_length_c 17.4233(9) _cell_measurement_reflns_used 3368 _cell_measurement_temperature 273 _cell_measurement_theta_max 64.0650 _cell_measurement_theta_min 4.6430 _cell_volume 3200.9(3) _computing_cell_refinement 'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)' _computing_data_collection 'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)' _computing_data_reduction 'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'olex2.solve 1.5 (Bourhis et al., 2015)' _diffrn_ambient_temperature 273 _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.984 _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 43.00 69.00 0.50 0.50 -- 42.30 -82.00 120.00 52 2 \w 83.00 122.00 0.50 0.50 -- 42.30 43.00-180.00 78 3 \w 17.00 64.00 0.50 0.50 -- 42.30 -82.00-180.00 94 4 \w 18.00 102.00 0.50 0.50 -- 42.30 65.00 -30.00 168 5 \w -47.00 65.00 0.50 0.50 -- 42.30 -32.00-180.00 224 6 \w 27.00 76.00 0.50 0.50 -- 42.30 43.00-180.00 98 7 \w -45.00 50.00 0.50 0.50 -- 42.30 -65.00 -30.00 190 8 \w 18.00 70.00 0.50 0.50 -- 42.30 -82.00 -90.00 104 9 \w -20.00 65.00 0.50 0.50 -- 42.30 -82.00 90.00 170 10 \w -39.00 7.00 0.50 0.50 -- 42.30 -82.00 120.00 92 11 \w -15.00 35.00 0.50 0.50 -- 42.30 -65.00 30.00 100 12 \w -43.00 -18.00 0.50 0.50 -- 42.30 -65.00 30.00 50 13 \w -44.00 -16.00 0.50 0.50 -- 42.30 -82.00 -90.00 56 14 \w 21.00 61.00 0.50 0.50 -- 42.30 -77.00-150.00 80 15 \w 31.00 66.00 0.50 0.50 -- 42.30 -82.00 60.00 70 16 \w 98.00 148.00 0.50 0.80 -- 93.70 82.00 -90.00 100 17 \w 50.00 101.00 0.50 0.80 -- 93.70 -82.00 -30.00 102 18 \w 70.00 96.00 0.50 0.80 -- 93.70 82.00 -90.00 52 19 \w 6.00 121.00 0.50 0.80 -- 93.70 -82.00 30.00 230 20 \w 12.00 99.00 0.50 0.80 -- 93.70 -82.00-180.00 174 21 \w 86.00 118.00 0.50 0.80 -- 93.70 -82.00-150.00 64 22 \w 68.00 183.00 0.50 0.80 -- 93.70 59.00 30.00 230 23 \w 68.00 94.00 0.50 0.80 -- 93.70 -82.00 -60.00 52 24 \w 45.00 121.00 0.50 0.80 -- 93.70 -82.00-120.00 152 25 \w 7.00 52.00 0.50 0.80 -- 93.70 -82.00 -60.00 90 26 \w 69.00 178.00 0.50 0.80 -- 93.70 68.00 0.00 218 27 \w 14.00 76.00 0.50 0.80 -- 93.70 -82.00-150.00 124 28 \w 24.00 102.00 0.50 0.80 -- 93.70 -82.00 90.00 156 29 \w 22.00 62.00 0.50 0.80 -- 93.70 -82.00 120.00 80 30 \w 76.00 102.00 0.50 0.80 -- 93.70 -82.00 120.00 52 31 \w 15.00 40.00 0.50 0.80 -- 93.70 -82.00 60.00 50 32 \w 81.00 106.00 0.50 0.80 -- 93.70 -82.00 -90.00 50 33 \w 18.00 44.00 0.50 0.80 -- 93.70 -82.00 -90.00 52 34 \w 23.00 71.00 0.50 0.80 -- 93.70 -82.00 150.00 96 35 \w 65.00 90.00 0.50 0.80 -- 93.70 -82.00 0.00 50 36 \w 69.00 151.00 0.50 0.80 -- 93.70 68.00 -30.00 164 37 \w 80.00 143.00 0.50 0.80 -- 93.70 68.00 60.00 126 38 \w 50.00 96.00 0.50 0.80 -- 93.70 -82.00 60.00 92 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Pro II AFC12 (RINC): Kappa single' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0520706000 _diffrn_orient_matrix_UB_12 0.0498894000 _diffrn_orient_matrix_UB_13 0.0691365000 _diffrn_orient_matrix_UB_21 0.0417268000 _diffrn_orient_matrix_UB_22 0.0847179000 _diffrn_orient_matrix_UB_23 -0.0533166000 _diffrn_orient_matrix_UB_31 -0.0783439000 _diffrn_orient_matrix_UB_32 0.0781629000 _diffrn_orient_matrix_UB_33 0.0139472000 _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 0.1406 _diffrn_reflns_av_unetI/netI 0.1096 _diffrn_reflns_Laue_measured_fraction_full 0.989 _diffrn_reflns_Laue_measured_fraction_max 0.984 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 13265 _diffrn_reflns_point_group_measured_fraction_full 0.989 _diffrn_reflns_point_group_measured_fraction_max 0.984 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 68.218 _diffrn_reflns_theta_min 4.659 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.567 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.14595 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020) 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 1.238 _exptl_crystal_description block _exptl_crystal_F_000 1264 _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.230 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.054 _refine_ls_extinction_coef 0.0008(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 212 _refine_ls_number_reflns 2887 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.078 _refine_ls_R_factor_all 0.0996 _refine_ls_R_factor_gt 0.0761 _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^)+(0.1284P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2163 _refine_ls_wR_factor_ref 0.2492 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1928 _reflns_number_total 2887 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6ee00605a7.cif _cod_data_source_block wls_auto _cod_database_code 1577420 _shelx_shelxl_version_number 2018/3 _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 0.935 _shelx_estimated_absorpt_t_min 0.753 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: C18(H18), C1(H1), C17(H17), C20(H20), C21(H21), C4(H4), C8(H8), C2(H2), C3(H3), C11(H11), C9(H9), C10(H10) 2.b Idealised Me refined as rotating group: C14(H14A,H14B,H14C), C15(H15A,H15B,H15C) ; _shelx_res_file ; TITL wls_auto_a.res in C2/c wls_auto.res created by SHELXL-2018/3 at 18:07:58 on 07-Oct-2023 REM Old TITL wls_auto_a.res in C2/c REM SHELXT solution in C2/c REM R1 0.197, Rweak 0.009, Alpha 0.021, Orientation as input REM Formula found by SHELXT: C43 N2 O CELL 1.54184 14.9752 12.274 17.4233 90 91.784 90 ZERR 4 0.0006 0.0006 0.0009 0 0.004 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H N O UNIT 172 144 8 4 L.S. 4 0 0 PLAN 1 SIZE 0.22 0.12 0.53 TEMP -0.15 CONF BOND $H list 4 MORE -1 fmap 2 53 acta REM REM REM WGHT 0.128400 EXTI 0.000836 FVAR 0.31883 O1 4 0.500000 0.847782 0.750000 10.50000 0.09966 0.06301 = 0.07400 0.00000 0.00691 0.00000 N1 3 0.303539 0.545236 0.503769 11.00000 0.05486 0.08197 = 0.05174 0.00394 -0.00371 0.00435 C5 1 0.284164 0.516918 0.366227 11.00000 0.06051 0.05658 = 0.05383 -0.00004 -0.00171 0.01361 C6 1 0.325978 0.572260 0.428192 11.00000 0.05258 0.06043 = 0.05429 0.00520 0.00088 0.01371 C22 1 0.500000 0.750086 0.750000 10.50000 0.06730 0.06494 = 0.05648 0.00000 0.01021 0.00000 C7 1 0.220311 0.494057 0.516316 11.00000 0.05730 0.06502 = 0.05638 0.00867 0.00078 0.00989 C19 1 0.447341 0.690183 0.688656 11.00000 0.05800 0.06393 = 0.05598 0.00481 0.00377 0.00625 C16 1 0.351245 0.595527 0.566905 11.00000 0.05873 0.07234 = 0.05328 0.00069 -0.00190 0.00925 C18 1 0.472664 0.589998 0.659822 11.00000 0.05798 0.07259 = 0.06012 0.00040 -0.00410 0.01384 AFIX 43 H18 2 0.521687 0.553792 0.681747 11.00000 -1.20000 AFIX 0 C1 1 0.388038 0.654639 0.414705 11.00000 0.05860 0.07281 = 0.06882 -0.00152 0.00003 0.00224 AFIX 43 H1 2 0.415996 0.690457 0.455895 11.00000 -1.20000 AFIX 0 C13 1 0.223822 0.420476 0.380626 11.00000 0.07194 0.05886 = 0.07030 0.00080 0.00277 0.00531 C17 1 0.425610 0.543550 0.598760 11.00000 0.06209 0.07055 = 0.06104 -0.00384 -0.00497 0.01642 AFIX 43 H17 2 0.443937 0.477124 0.578964 11.00000 -1.20000 AFIX 0 C12 1 0.177471 0.436206 0.456650 11.00000 0.06218 0.06080 = 0.06862 0.00881 0.00232 0.00787 C20 1 0.372760 0.741474 0.655990 11.00000 0.07419 0.06706 = 0.07514 -0.00612 0.00004 0.02130 AFIX 43 H20 2 0.354697 0.808426 0.675097 11.00000 -1.20000 AFIX 0 C21 1 0.325331 0.694725 0.595893 11.00000 0.06731 0.08419 = 0.07155 -0.00025 -0.00992 0.02955 AFIX 43 H21 2 0.275519 0.730108 0.574645 11.00000 -1.20000 AFIX 0 C4 1 0.306327 0.549000 0.293084 11.00000 0.07924 0.07346 = 0.05588 -0.00005 -0.00095 0.00820 AFIX 43 H4 2 0.279075 0.514000 0.251208 11.00000 -1.20000 AFIX 0 C8 1 0.181552 0.500189 0.587798 11.00000 0.07315 0.09442 = 0.06626 0.01064 0.00625 0.00791 AFIX 43 H8 2 0.210510 0.538483 0.627335 11.00000 -1.20000 AFIX 0 C2 1 0.408024 0.683088 0.340403 11.00000 0.06977 0.07756 = 0.07994 0.01012 0.00881 0.00142 AFIX 43 H2 2 0.449356 0.737951 0.331785 11.00000 -1.20000 AFIX 0 C3 1 0.367263 0.630877 0.279663 11.00000 0.08432 0.08009 = 0.06583 0.01261 0.01229 0.00891 AFIX 43 H3 2 0.380383 0.650233 0.229654 11.00000 -1.20000 AFIX 0 C11 1 0.096080 0.387419 0.472044 11.00000 0.07307 0.08650 = 0.09895 0.00196 0.00544 -0.01035 AFIX 43 H11 2 0.065867 0.349034 0.433233 11.00000 -1.20000 AFIX 0 C9 1 0.101364 0.450659 0.600818 11.00000 0.07860 0.10758 = 0.07816 0.01371 0.02041 0.00734 AFIX 43 H9 2 0.076146 0.455561 0.648804 11.00000 -1.20000 AFIX 0 C10 1 0.059022 0.394525 0.543441 11.00000 0.07233 0.10133 = 0.11454 0.02045 0.01986 -0.00869 AFIX 43 H10 2 0.004741 0.360629 0.552205 11.00000 -1.20000 AFIX 0 C14 1 0.282726 0.318031 0.389207 11.00000 0.12409 0.06313 = 0.12610 0.00640 0.04377 0.02300 AFIX 137 H14A 2 0.310525 0.303172 0.341413 11.00000 -1.50000 H14B 2 0.246406 0.257066 0.402994 11.00000 -1.50000 H14C 2 0.327953 0.330017 0.428561 11.00000 -1.50000 AFIX 0 C15 1 0.154810 0.405056 0.314214 11.00000 0.11084 0.10444 = 0.08810 -0.01256 -0.00721 -0.03153 AFIX 137 H15A 2 0.120902 0.470865 0.307129 11.00000 -1.50000 H15B 2 0.115310 0.346264 0.326158 11.00000 -1.50000 H15C 2 0.185166 0.388421 0.267926 11.00000 -1.50000 AFIX 0 HKLF 4 REM wls_auto_a.res in C2/c REM wR2 = 0.2492, GooF = S = 1.078, Restrained GooF = 1.078 for all data REM R1 = 0.0761 for 1928 Fo > 4sig(Fo) and 0.0996 for all 2887 data REM 212 parameters refined using 0 restraints END WGHT 0.1284 0.0000 REM Highest difference peak 0.230, deepest hole -0.223, 1-sigma level 0.054 Q1 1 0.4038 0.7120 0.4639 11.00000 0.05 0.21 ; _shelx_res_checksum 16643 _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 6.899 _oxdiff_exptl_absorpt_empirical_full_min 0.202 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' 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 O1 O 0.500000 0.8478(2) 0.750000 0.0788(8) Uani 1 2 d S T P . . N1 N 0.30354(13) 0.54524(18) 0.50377(12) 0.0630(6) Uani 1 1 d . . . . . C5 C 0.28416(16) 0.51692(19) 0.36623(14) 0.0570(6) Uani 1 1 d . . . . . C6 C 0.32598(15) 0.57226(19) 0.42819(14) 0.0558(6) Uani 1 1 d . . . . . C22 C 0.500000 0.7501(3) 0.750000 0.0627(9) Uani 1 2 d S T P . . C7 C 0.22031(15) 0.4941(2) 0.51632(14) 0.0596(7) Uani 1 1 d . . . . . C19 C 0.44734(16) 0.6902(2) 0.68866(14) 0.0593(7) Uani 1 1 d . . . . . C16 C 0.35125(16) 0.5955(2) 0.56691(15) 0.0615(7) Uani 1 1 d . . . . . C18 C 0.47266(16) 0.5900(2) 0.65982(15) 0.0637(7) Uani 1 1 d . . . . . H18 H 0.521687 0.553792 0.681747 0.076 Uiso 1 1 calc R U . . . C1 C 0.38804(16) 0.6546(2) 0.41470(16) 0.0668(7) Uani 1 1 d . . . . . H1 H 0.415996 0.690457 0.455895 0.080 Uiso 1 1 calc R U . . . C13 C 0.22382(18) 0.4205(2) 0.38063(17) 0.0670(7) Uani 1 1 d . . . . . C17 C 0.42561(16) 0.5435(2) 0.59876(15) 0.0647(7) Uani 1 1 d . . . . . H17 H 0.443937 0.477124 0.578964 0.078 Uiso 1 1 calc R U . . . C12 C 0.17747(17) 0.4362(2) 0.45665(16) 0.0639(7) Uani 1 1 d . . . . . C20 C 0.37276(18) 0.7415(2) 0.65599(16) 0.0722(8) Uani 1 1 d . . . . . H20 H 0.354697 0.808426 0.675097 0.087 Uiso 1 1 calc R U . . . C21 C 0.32533(18) 0.6947(2) 0.59589(16) 0.0746(8) Uani 1 1 d . . . . . H21 H 0.275519 0.730108 0.574645 0.090 Uiso 1 1 calc R U . . . C4 C 0.30633(19) 0.5490(2) 0.29308(16) 0.0696(8) Uani 1 1 d . . . . . H4 H 0.279075 0.514000 0.251208 0.084 Uiso 1 1 calc R U . . . C8 C 0.18155(19) 0.5002(3) 0.58780(17) 0.0779(8) Uani 1 1 d . . . . . H8 H 0.210510 0.538483 0.627335 0.093 Uiso 1 1 calc R U . . . C2 C 0.40802(19) 0.6831(3) 0.34040(18) 0.0756(8) Uani 1 1 d . . . . . H2 H 0.449356 0.737951 0.331785 0.091 Uiso 1 1 calc R U . . . C3 C 0.3673(2) 0.6309(2) 0.27966(18) 0.0765(9) Uani 1 1 d . . . . . H3 H 0.380383 0.650233 0.229654 0.092 Uiso 1 1 calc R U . . . C11 C 0.0961(2) 0.3874(3) 0.4720(2) 0.0861(9) Uani 1 1 d . . . . . H11 H 0.065867 0.349034 0.433233 0.103 Uiso 1 1 calc R U . . . C9 C 0.1014(2) 0.4507(3) 0.6008(2) 0.0877(10) Uani 1 1 d . . . . . H9 H 0.076146 0.455561 0.648804 0.105 Uiso 1 1 calc R U . . . C10 C 0.0590(2) 0.3945(3) 0.5434(2) 0.0957(11) Uani 1 1 d . . . . . H10 H 0.004741 0.360629 0.552205 0.115 Uiso 1 1 calc R U . . . C14 C 0.2827(3) 0.3180(2) 0.3892(2) 0.1036(12) Uani 1 1 d . . . . . H14A H 0.310525 0.303172 0.341413 0.155 Uiso 1 1 calc R U . . . H14B H 0.246406 0.257066 0.402994 0.155 Uiso 1 1 calc R U . . . H14C H 0.327953 0.330017 0.428561 0.155 Uiso 1 1 calc R U . . . C15 C 0.1548(3) 0.4051(3) 0.3142(2) 0.1013(11) Uani 1 1 d . . . . . H15A H 0.120902 0.470865 0.307129 0.152 Uiso 1 1 calc R U . . . H15B H 0.115310 0.346264 0.326158 0.152 Uiso 1 1 calc R U . . . H15C H 0.185166 0.388421 0.267926 0.152 Uiso 1 1 calc R U . . . 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 O1 0.100(2) 0.0630(17) 0.0740(19) 0.000 0.0069(14) 0.000 N1 0.0549(11) 0.0820(15) 0.0517(13) 0.0039(10) -0.0037(9) 0.0043(10) C5 0.0605(13) 0.0566(14) 0.0538(15) 0.0000(11) -0.0017(10) 0.0136(11) C6 0.0526(13) 0.0604(14) 0.0543(15) 0.0052(10) 0.0009(10) 0.0137(11) C22 0.067(2) 0.065(2) 0.056(2) 0.000 0.0102(16) 0.000 C7 0.0573(14) 0.0650(15) 0.0564(16) 0.0087(11) 0.0008(10) 0.0099(12) C19 0.0580(13) 0.0639(15) 0.0560(15) 0.0048(11) 0.0038(10) 0.0062(12) C16 0.0587(14) 0.0723(16) 0.0533(15) 0.0007(12) -0.0019(11) 0.0093(12) C18 0.0580(14) 0.0726(17) 0.0601(16) 0.0004(12) -0.0041(11) 0.0138(13) C1 0.0586(14) 0.0728(16) 0.0688(18) -0.0015(13) 0.0000(11) 0.0022(13) C13 0.0719(15) 0.0589(15) 0.0703(18) 0.0008(12) 0.0028(12) 0.0053(13) C17 0.0621(14) 0.0705(16) 0.0610(17) -0.0038(12) -0.0050(11) 0.0164(13) C12 0.0622(15) 0.0608(15) 0.0686(18) 0.0088(12) 0.0023(12) 0.0079(12) C20 0.0742(16) 0.0671(16) 0.075(2) -0.0061(13) 0.0000(13) 0.0213(14) C21 0.0673(16) 0.0842(19) 0.0716(19) -0.0002(15) -0.0099(13) 0.0296(14) C4 0.0792(17) 0.0735(17) 0.0559(17) 0.0000(12) -0.0009(12) 0.0082(15) C8 0.0731(17) 0.094(2) 0.0663(19) 0.0106(15) 0.0062(13) 0.0079(16) C2 0.0698(16) 0.0776(19) 0.080(2) 0.0101(15) 0.0088(14) 0.0014(14) C3 0.0843(19) 0.0801(19) 0.0658(19) 0.0126(14) 0.0123(14) 0.0089(16) C11 0.0731(18) 0.086(2) 0.099(3) 0.0020(17) 0.0054(16) -0.0104(16) C9 0.079(2) 0.108(2) 0.078(2) 0.0137(18) 0.0204(16) 0.0073(19) C10 0.0723(19) 0.101(2) 0.115(3) 0.020(2) 0.0199(19) -0.0087(18) C14 0.124(3) 0.0631(18) 0.126(3) 0.0064(18) 0.044(2) 0.0230(19) C15 0.111(2) 0.104(3) 0.088(3) -0.0126(19) -0.0072(19) -0.032(2) 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_ _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 C6 N1 C7 119.0(2) . . ? C6 N1 C16 119.2(2) . . ? C7 N1 C16 119.5(2) . . ? C6 C5 C13 120.3(2) . . ? C4 C5 C6 117.1(2) . . ? C4 C5 C13 122.4(2) . . ? C5 C6 N1 119.4(2) . . ? C1 C6 N1 120.4(2) . . ? C1 C6 C5 120.2(2) . . ? O1 C22 C19 119.34(16) . 2_656 ? O1 C22 C19 119.33(16) . . ? C19 C22 C19 121.3(3) . 2_656 ? C12 C7 N1 119.7(2) . . ? C8 C7 N1 120.4(2) . . ? C8 C7 C12 119.9(2) . . ? C18 C19 C22 123.3(2) . . ? C18 C19 C20 118.6(2) . . ? C20 C19 C22 117.9(2) . . ? C17 C16 N1 119.0(2) . . ? C21 C16 N1 121.5(2) . . ? C21 C16 C17 119.5(2) . . ? C19 C18 H18 119.8 . . ? C17 C18 C19 120.5(2) . . ? C17 C18 H18 119.8 . . ? C6 C1 H1 119.9 . . ? C2 C1 C6 120.3(3) . . ? C2 C1 H1 119.9 . . ? C5 C13 C12 109.5(2) . . ? C5 C13 C14 108.1(2) . . ? C5 C13 C15 111.2(2) . . ? C12 C13 C14 107.1(2) . . ? C12 C13 C15 110.8(2) . . ? C15 C13 C14 110.0(3) . . ? C16 C17 H17 119.9 . . ? C18 C17 C16 120.2(2) . . ? C18 C17 H17 119.9 . . ? C7 C12 C13 119.9(2) . . ? C11 C12 C7 117.4(3) . . ? C11 C12 C13 122.5(3) . . ? C19 C20 H20 119.5 . . ? C21 C20 C19 120.9(2) . . ? C21 C20 H20 119.5 . . ? C16 C21 H21 119.9 . . ? C20 C21 C16 120.3(2) . . ? C20 C21 H21 119.9 . . ? C5 C4 H4 118.6 . . ? C3 C4 C5 122.8(3) . . ? C3 C4 H4 118.6 . . ? C7 C8 H8 119.5 . . ? C9 C8 C7 121.0(3) . . ? C9 C8 H8 119.5 . . ? C1 C2 H2 119.9 . . ? C3 C2 C1 120.2(3) . . ? C3 C2 H2 119.9 . . ? C4 C3 H3 120.3 . . ? C2 C3 C4 119.5(3) . . ? C2 C3 H3 120.3 . . ? C12 C11 H11 119.1 . . ? C10 C11 C12 121.7(3) . . ? C10 C11 H11 119.1 . . ? C8 C9 H9 120.2 . . ? C10 C9 C8 119.7(3) . . ? C10 C9 H9 120.2 . . ? C11 C10 H10 119.8 . . ? C9 C10 C11 120.3(3) . . ? C9 C10 H10 119.8 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? 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 O1 C22 1.199(4) . ? N1 C6 1.409(3) . ? N1 C7 1.419(3) . ? N1 C16 1.433(3) . ? C5 C6 1.406(4) . ? C5 C13 1.515(4) . ? C5 C4 1.384(4) . ? C6 C1 1.398(4) . ? C22 C19 1.501(3) . ? C22 C19 1.501(3) 2_656 ? C7 C12 1.398(4) . ? C7 C8 1.392(4) . ? C19 C18 1.386(3) . ? C19 C20 1.389(3) . ? C16 C17 1.384(3) . ? C16 C21 1.379(4) . ? C18 H18 0.9300 . ? C18 C17 1.381(4) . ? C1 H1 0.9300 . ? C1 C2 1.383(4) . ? C13 C12 1.527(4) . ? C13 C14 1.541(4) . ? C13 C15 1.539(5) . ? C17 H17 0.9300 . ? C12 C11 1.392(4) . ? C20 H20 0.9300 . ? C20 C21 1.373(4) . ? C21 H21 0.9300 . ? C4 H4 0.9300 . ? C4 C3 1.382(4) . ? C8 H8 0.9300 . ? C8 C9 1.371(4) . ? C2 H2 0.9300 . ? C2 C3 1.365(4) . ? C3 H3 0.9300 . ? C11 H11 0.9300 . ? C11 C10 1.381(5) . ? C9 H9 0.9300 . ? C9 C10 1.355(5) . ? C10 H10 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? 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 O1 C22 C19 C18 148.08(19) . . . . ? O1 C22 C19 C20 -27.6(2) . . . . ? N1 C6 C1 C2 -178.2(2) . . . . ? N1 C7 C12 C13 5.0(3) . . . . ? N1 C7 C12 C11 179.9(2) . . . . ? N1 C7 C8 C9 -179.7(3) . . . . ? N1 C16 C17 C18 -179.8(2) . . . . ? N1 C16 C21 C20 -179.4(2) . . . . ? C5 C6 C1 C2 0.7(3) . . . . ? C5 C13 C12 C7 -30.6(3) . . . . ? C5 C13 C12 C11 154.8(3) . . . . ? C5 C4 C3 C2 0.1(4) . . . . ? C6 N1 C7 C12 23.3(3) . . . . ? C6 N1 C7 C8 -157.4(2) . . . . ? C6 N1 C16 C17 -92.6(3) . . . . ? C6 N1 C16 C21 86.7(3) . . . . ? C6 C5 C13 C12 31.7(3) . . . . ? C6 C5 C13 C14 -84.6(3) . . . . ? C6 C5 C13 C15 154.5(2) . . . . ? C6 C5 C4 C3 0.6(4) . . . . ? C6 C1 C2 C3 0.0(4) . . . . ? C22 C19 C18 C17 -174.3(2) . . . . ? C22 C19 C20 C21 175.3(2) . . . . ? C7 N1 C6 C5 -22.2(3) . . . . ? C7 N1 C6 C1 156.6(2) . . . . ? C7 N1 C16 C17 104.9(3) . . . . ? C7 N1 C16 C21 -75.9(3) . . . . ? C7 C12 C11 C10 -0.6(4) . . . . ? C7 C8 C9 C10 0.2(5) . . . . ? C19 C22 C19 C18 -31.92(19) 2_656 . . . ? C19 C22 C19 C20 152.4(2) 2_656 . . . ? C19 C18 C17 C16 -1.6(4) . . . . ? C19 C20 C21 C16 0.0(5) . . . . ? C16 N1 C6 C5 175.10(19) . . . . ? C16 N1 C6 C1 -6.0(3) . . . . ? C16 N1 C7 C12 -174.1(2) . . . . ? C16 N1 C7 C8 5.3(3) . . . . ? C18 C19 C20 C21 -0.6(4) . . . . ? C1 C2 C3 C4 -0.4(4) . . . . ? C13 C5 C6 N1 -7.1(3) . . . . ? C13 C5 C6 C1 174.0(2) . . . . ? C13 C5 C4 C3 -174.3(2) . . . . ? C13 C12 C11 C10 174.1(3) . . . . ? C17 C16 C21 C20 -0.2(4) . . . . ? C12 C7 C8 C9 -0.3(4) . . . . ? C12 C11 C10 C9 0.5(5) . . . . ? C20 C19 C18 C17 1.4(4) . . . . ? C21 C16 C17 C18 0.9(4) . . . . ? C4 C5 C6 N1 177.9(2) . . . . ? C4 C5 C6 C1 -1.0(3) . . . . ? C4 C5 C13 C12 -153.5(2) . . . . ? C4 C5 C13 C14 90.1(3) . . . . ? C4 C5 C13 C15 -30.7(3) . . . . ? C8 C7 C12 C13 -174.3(2) . . . . ? C8 C7 C12 C11 0.5(4) . . . . ? C8 C9 C10 C11 -0.3(5) . . . . ? C14 C13 C12 C7 86.4(3) . . . . ? C14 C13 C12 C11 -88.2(3) . . . . ? C15 C13 C12 C7 -153.7(2) . . . . ? C15 C13 C12 C11 31.7(4) . . . . ?