#------------------------------------------------------------------------------ #$Date: 2021-12-07 05:53:38 +0200 (Tue, 07 Dec 2021) $ #$Revision: 271222 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158384.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_7158384 loop_ _publ_author_name 'Fuller, Rebecca O.' 'Taylor, Madeleine R.' 'Duggin, Margot' 'Bissember, Alex C.' 'Canty, Allan J.' 'Judd, Martyna M.' 'Cox, Nicholas' 'Moggach, Stephen A.' 'Turner, Gemma F.' _publ_section_title ; Enhanced synthesis of oxo-verdazyl radicals bearing sterically-and electronically-diverse C3-substituents. ; _journal_issue 46 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 10120 _journal_page_last 10138 _journal_paper_doi 10.1039/d1ob01946e _journal_volume 19 _journal_year 2021 _chemical_formula_moiety 'C15 H16 N6 O' _chemical_formula_sum 'C15 H16 N6 O' _chemical_formula_weight 296.34 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2021-09-17 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) ; _audit_update_record ; 2021-09-30 deposited with the CCDC. 2021-11-01 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 98.940(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.4529(3) _cell_length_b 10.4903(3) _cell_length_c 12.3136(4) _cell_measurement_reflns_used 12819 _cell_measurement_temperature 99.9(4) _cell_measurement_theta_max 74.6590 _cell_measurement_theta_min 3.8730 _cell_volume 1461.44(7) _computing_cell_refinement 'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)' _computing_data_collection 'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)' _computing_data_reduction 'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 99.9(4) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.964 _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 -28.00 26.00 0.50 0.05 -- 46.20 -19.00 0.00 108 2 \w 30.00 105.00 0.50 0.15 -- 102.41 -77.00 -30.00 150 3 \w 37.00 70.00 0.50 0.15 -- 102.41 -61.00-180.00 66 4 \w -28.00 26.00 0.50 0.05 -- 46.20 -19.00 90.00 108 5 \w 86.00 175.00 0.50 0.15 -- 102.41 61.00 0.00 178 6 \w 49.00 118.00 0.50 0.05 -- 46.20 162.00-172.00 138 7 \w 30.00 109.00 0.50 0.15 -- 102.41-117.00 -50.00 158 8 \w 30.00 111.00 0.50 0.15 -- 102.41-125.00 -90.00 162 9 \w 36.00 75.00 0.50 0.15 -- 102.41-125.00 0.00 78 10 \w 81.00 111.00 0.50 0.15 -- 102.41-125.00 0.00 60 11 \w 32.00 118.00 0.50 0.05 -- 46.20-162.00 159.00 172 12 \w 32.00 136.00 0.50 0.15 -- 102.41-162.00 159.00 208 13 \w 36.00 105.00 0.50 0.15 -- 102.41-125.00 150.00 138 14 \w 7.00 90.00 0.50 0.05 -- 46.20-117.00 -50.00 166 15 \w -109.00 -30.00 0.50 0.15 -- -102.41 117.00 37.00 158 16 \w -111.00 -30.00 0.50 0.15 -- -102.41 125.00 150.00 162 17 \w -123.00 -30.00 0.50 0.15 -- -102.41 141.00 41.65 186 18 \w -90.00 -7.00 0.50 0.05 -- -46.20 117.00 37.00 166 19 \w -117.00 -31.00 0.50 0.05 -- -46.20 162.00-172.00 172 20 \w -136.00 -31.00 0.50 0.15 -- -102.41 162.00-172.00 210 21 \w -71.00 -30.00 0.50 0.15 -- -102.41 61.00 0.00 82 22 \w -71.00 -30.00 0.50 0.15 -- -102.41 61.00 60.00 82 23 \w -105.00 -30.00 0.50 0.15 -- -102.41 77.00 60.00 150 24 \w -71.00 -30.00 0.50 0.15 -- -102.41 61.00-150.00 82 25 \w -71.00 -30.00 0.50 0.15 -- -102.41 61.00-120.00 82 26 \w -175.00 -90.00 0.50 0.15 -- -102.41 -46.00 39.76 170 27 \w -175.00 -84.00 0.50 0.15 -- -102.41 -65.00 176.91 182 28 \w -175.00 -89.00 0.50 0.15 -- -102.41 -52.00 101.86 172 29 \w -118.00 -23.00 0.50 0.05 -- -46.20 -77.00-120.00 190 30 \w -175.00 -80.00 0.50 0.15 -- -102.41 -77.00-112.23 190 31 \w -175.00 -88.00 0.50 0.15 -- -102.41 -54.00-139.96 174 32 \w -118.00 -73.00 0.50 0.05 -- -46.20-125.00 0.00 90 33 \w -118.00 -73.00 0.50 0.05 -- -46.20-125.00 60.00 90 34 \w -118.00 -49.00 0.50 0.05 -- -46.20-162.00 159.00 138 35 \w -156.00 -49.00 0.50 0.15 -- -102.41-162.00 159.00 214 36 \w -175.00 -73.00 0.50 0.15 -- -102.41-125.00 90.00 204 37 \w -175.00 -78.00 0.50 0.15 -- -102.41-117.00 -50.00 194 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Single source at home/near, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0164323000 _diffrn_orient_matrix_UB_12 0.1444264000 _diffrn_orient_matrix_UB_13 -0.0196920000 _diffrn_orient_matrix_UB_21 0.0280673000 _diffrn_orient_matrix_UB_22 -0.0166655000 _diffrn_orient_matrix_UB_23 -0.1175695000 _diffrn_orient_matrix_UB_31 -0.1324994000 _diffrn_orient_matrix_UB_32 -0.0212982000 _diffrn_orient_matrix_UB_33 -0.0419917000 _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 0.1014 _diffrn_reflns_av_unetI/netI 0.0572 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.964 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 25448 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.964 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.079 _diffrn_reflns_theta_min 3.907 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.739 _exptl_absorpt_correction_T_max 0.6814 _exptl_absorpt_correction_T_min 0.5382 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1440 before and 0.1138 after correction. The Ratio of minimum to maximum transmission is 0.7898. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_density_diffrn 1.347 _exptl_crystal_description block _exptl_crystal_F_000 624 _exptl_crystal_size_max 0.214 _exptl_crystal_size_mid 0.188 _exptl_crystal_size_min 0.084 _refine_diff_density_max 0.409 _refine_diff_density_min -0.425 _refine_diff_density_rms 0.086 _refine_ls_extinction_coef 0.0039(13) _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 1.116 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 202 _refine_ls_number_reflns 2957 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.116 _refine_ls_R_factor_all 0.0700 _refine_ls_R_factor_gt 0.0646 _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^)+(0.1461P)^2^+0.2626P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1917 _refine_ls_wR_factor_ref 0.2096 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2593 _reflns_number_total 2957 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01946e2.cif _cod_data_source_block 9b _cod_depositor_comments 'Adding full bibliography for 7158376--7158384.cif.' _cod_database_code 7158384 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'N4 C20 H20 O1' _chemical_oxdiff_usercomment 'UTas sample' _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. ; _reflns_odcompleteness_completeness 100.00 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.49 _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: C009(H009), C00A(H00A), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00K(H00K), C00M(H00O) 2.b Idealised Me refined as rotating group: C00J(H00B,H00C,H00J), C00L(H00L,H00M,H00N) ; _shelx_res_file ; TITL bof7_a.res in P2(1)/c bof7.res created by SHELXL-2018/3 at 16:32:40 on 17-Sep-2021 REM Old TITL BOF7 in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.206, Rweak 0.024, Alpha 0.012 REM 0.322 for 178 systematic absences, Orientation as input REM Formula found by SHELXT: C18 N3 O CELL 1.54184 11.4529 10.4903 12.3136 90 98.94 90 ZERR 4 0.0003 0.0003 0.0004 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 60 64 24 4 L.S. 4 0 0 PLAN 5 CONF list 4 MORE -1 BOND $H fmap 2 53 acta OMIT -2 0 2 OMIT 6 6 11 REM REM REM WGHT 0.146100 0.262600 EXTI 0.003893 FVAR 0.69384 O001 4 1.011136 0.386035 0.119034 11.00000 0.02238 0.02928 = 0.03014 0.00055 0.00246 -0.00189 N002 3 0.727031 0.363954 0.175117 11.00000 0.02006 0.01850 = 0.02658 -0.00078 0.00086 -0.00110 N003 3 0.883401 0.395989 0.355845 11.00000 0.02101 0.01997 = 0.02571 -0.00171 -0.00035 -0.00106 N004 3 0.817297 0.421502 0.132756 11.00000 0.01959 0.02349 = 0.02547 0.00332 -0.00109 -0.00175 N005 3 0.954510 0.349987 0.285522 11.00000 0.02021 0.02460 = 0.02170 -0.00051 -0.00116 0.00204 N006 3 0.420440 0.308493 0.103241 11.00000 0.02222 0.02269 = 0.03002 -0.00071 -0.00276 -0.00024 N007 3 0.873451 0.392632 0.641625 11.00000 0.02666 0.02310 = 0.02670 0.00186 0.00152 -0.00022 C008 1 0.525199 0.311194 0.169842 11.00000 0.02111 0.01802 = 0.02664 -0.00177 -0.00035 0.00177 C009 1 0.907895 0.366437 0.458262 11.00000 0.02032 0.02158 = 0.02716 0.00141 -0.00088 -0.00071 AFIX 43 H009 2 0.973536 0.316372 0.483487 11.00000 -1.20000 AFIX 0 C00A 1 0.621253 0.374856 0.123569 11.00000 0.02268 0.02088 = 0.02454 0.00169 -0.00198 0.00068 AFIX 43 H00A 2 0.605536 0.421623 0.058781 11.00000 -1.20000 AFIX 0 C00B 1 0.932441 0.385124 0.176609 11.00000 0.01931 0.01965 = 0.02841 -0.00119 -0.00020 -0.00290 C00C 1 0.831371 0.412438 0.534653 11.00000 0.02375 0.01848 = 0.02826 -0.00030 -0.00234 -0.00336 C00D 1 0.450021 0.193260 0.309991 11.00000 0.02920 0.02277 = 0.03252 0.00508 0.00193 0.00209 AFIX 43 H00D 2 0.459459 0.156231 0.379428 11.00000 -1.20000 AFIX 0 C00E 1 0.542590 0.257145 0.274595 11.00000 0.02159 0.02418 = 0.02777 -0.00026 -0.00005 0.00080 AFIX 43 H00E 2 0.615302 0.264014 0.319841 11.00000 -1.20000 AFIX 0 C00F 1 0.343051 0.185184 0.240596 11.00000 0.02304 0.02255 = 0.03920 0.00128 0.00466 -0.00060 AFIX 43 H00F 2 0.280172 0.139917 0.261159 11.00000 -1.20000 AFIX 0 C00G 1 0.697668 0.490811 0.687623 11.00000 0.03190 0.02227 = 0.03641 -0.00509 0.00645 -0.00245 AFIX 43 H00G 2 0.654480 0.516581 0.741777 11.00000 -1.20000 AFIX 0 C00H 1 0.806181 0.431133 0.714704 11.00000 0.03345 0.02431 = 0.02657 0.00044 0.00445 -0.00226 AFIX 43 H00H 2 0.834031 0.416940 0.788753 11.00000 -1.20000 AFIX 0 C00I 1 0.331878 0.245955 0.140053 11.00000 0.01946 0.02521 = 0.03738 -0.00059 -0.00229 0.00019 AFIX 43 H00I 2 0.258718 0.243480 0.095107 11.00000 -1.20000 AFIX 0 C00J 1 0.797568 0.479758 0.024462 11.00000 0.02583 0.03006 = 0.02672 0.00512 -0.00046 -0.00204 AFIX 137 H00B 2 0.765639 0.417465 -0.029156 11.00000 -1.50000 H00C 2 0.871168 0.511152 0.006996 11.00000 -1.50000 H00J 2 0.742856 0.549164 0.023959 11.00000 -1.50000 AFIX 0 C00K 1 0.722118 0.470466 0.499444 11.00000 0.02830 0.02442 = 0.03044 -0.00205 -0.00337 0.00044 AFIX 43 H00K 2 0.694836 0.481607 0.424891 11.00000 -1.20000 AFIX 0 C00L 1 1.057813 0.271219 0.322676 11.00000 0.02198 0.03044 = 0.03183 -0.00004 -0.00316 0.00382 AFIX 137 H00L 2 1.114912 0.320050 0.370870 11.00000 -1.50000 H00M 2 1.091999 0.243408 0.260311 11.00000 -1.50000 H00N 2 1.034581 0.198310 0.361324 11.00000 -1.50000 AFIX 0 C00M 1 0.655447 0.510923 0.577057 11.00000 0.02475 0.02703 = 0.04049 -0.00437 0.00058 0.00162 AFIX 43 H00O 2 0.583177 0.551136 0.555593 11.00000 -1.20000 AFIX 0 HKLF 4 REM bof7_a.res in P2(1)/c REM wR2 = 0.209555, GooF = S = 1.11590, Restrained GooF = 1.11590 for all data REM R1 = 0.064563 for 2593 Fo > 4sig(Fo) and 0.070034 for all 2957 data REM 202 parameters refined using 0 restraints END WGHT 0.1460 0.2639 REM Highest difference peak 0.409, deepest hole -0.425, 1-sigma level 0.086 Q1 1 0.8057 0.4038 0.2944 11.00000 0.05 0.41 Q2 1 0.7565 0.3963 0.4841 11.00000 0.05 0.37 Q3 1 0.3984 0.2038 0.2800 11.00000 0.05 0.36 Q4 1 0.7214 0.3837 0.2830 11.00000 0.05 0.34 Q5 1 0.8465 0.4078 0.1337 11.00000 0.05 0.32 ; _shelx_res_checksum 20773 _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 1.766 _oxdiff_exptl_absorpt_empirical_full_min 0.655 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 O001 O 1.01114(10) 0.38603(12) 0.11903(10) 0.0274(4) Uani 1 1 d . . . . . N002 N 0.72703(12) 0.36395(13) 0.17512(12) 0.0220(4) Uani 1 1 d . . . . . N003 N 0.88340(12) 0.39599(13) 0.35584(12) 0.0227(4) Uani 1 1 d . . . . . N004 N 0.81730(12) 0.42150(14) 0.13276(12) 0.0233(4) Uani 1 1 d . . . . . N005 N 0.95451(12) 0.34999(14) 0.28552(12) 0.0226(4) Uani 1 1 d . . . . . N006 N 0.42044(13) 0.30849(14) 0.10324(13) 0.0257(4) Uani 1 1 d . . . . . N007 N 0.87345(13) 0.39263(14) 0.64163(12) 0.0258(4) Uani 1 1 d . . . . . C008 C 0.52520(14) 0.31119(15) 0.16984(14) 0.0224(4) Uani 1 1 d . . . . . C009 C 0.90790(15) 0.36644(16) 0.45826(14) 0.0235(4) Uani 1 1 d . . . . . H009 H 0.973536 0.316372 0.483487 0.028 Uiso 1 1 calc R U . . . C00A C 0.62125(15) 0.37486(16) 0.12357(14) 0.0233(4) Uani 1 1 d . . . . . H00A H 0.605536 0.421623 0.058781 0.028 Uiso 1 1 calc R U . . . C00B C 0.93244(15) 0.38512(16) 0.17661(15) 0.0229(4) Uani 1 1 d . . . . . C00C C 0.83137(15) 0.41244(16) 0.53465(15) 0.0242(4) Uani 1 1 d . . . . . C00D C 0.45002(16) 0.19326(17) 0.30999(16) 0.0285(4) Uani 1 1 d . . . . . H00D H 0.459459 0.156231 0.379428 0.034 Uiso 1 1 calc R U . . . C00E C 0.54259(15) 0.25715(16) 0.27459(15) 0.0249(4) Uani 1 1 d . . . . . H00E H 0.615302 0.264014 0.319841 0.030 Uiso 1 1 calc R U . . . C00F C 0.34305(16) 0.18518(17) 0.24060(17) 0.0283(4) Uani 1 1 d . . . . . H00F H 0.280172 0.139917 0.261159 0.034 Uiso 1 1 calc R U . . . C00G C 0.69767(17) 0.49081(17) 0.68762(17) 0.0301(5) Uani 1 1 d . . . . . H00G H 0.654480 0.516581 0.741777 0.036 Uiso 1 1 calc R U . . . C00H C 0.80618(17) 0.43113(17) 0.71470(15) 0.0281(4) Uani 1 1 d . . . . . H00H H 0.834031 0.416940 0.788753 0.034 Uiso 1 1 calc R U . . . C00I C 0.33188(15) 0.24595(17) 0.14005(16) 0.0281(4) Uani 1 1 d . . . . . H00I H 0.258718 0.243480 0.095107 0.034 Uiso 1 1 calc R U . . . C00J C 0.79757(16) 0.47976(18) 0.02446(14) 0.0280(4) Uani 1 1 d . . . . . H00B H 0.765639 0.417465 -0.029156 0.042 Uiso 1 1 calc R U . . . H00C H 0.871168 0.511152 0.006996 0.042 Uiso 1 1 calc R U . . . H00J H 0.742856 0.549164 0.023959 0.042 Uiso 1 1 calc R U . . . C00K C 0.72212(16) 0.47047(17) 0.49944(16) 0.0286(4) Uani 1 1 d . . . . . H00K H 0.694836 0.481607 0.424891 0.034 Uiso 1 1 calc R U . . . C00L C 1.05781(15) 0.27122(18) 0.32268(16) 0.0289(5) Uani 1 1 d . . . . . H00L H 1.114912 0.320050 0.370870 0.043 Uiso 1 1 calc R U . . . H00M H 1.091999 0.243408 0.260311 0.043 Uiso 1 1 calc R U . . . H00N H 1.034581 0.198310 0.361324 0.043 Uiso 1 1 calc R U . . . C00M C 0.65545(16) 0.51092(18) 0.57706(17) 0.0312(5) Uani 1 1 d . . . . . H00O H 0.583177 0.551136 0.555593 0.037 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 O001 0.0224(7) 0.0293(7) 0.0301(7) 0.0005(5) 0.0025(5) -0.0019(5) N002 0.0201(7) 0.0185(7) 0.0266(7) -0.0008(5) 0.0009(6) -0.0011(5) N003 0.0210(7) 0.0200(7) 0.0257(8) -0.0017(5) -0.0004(6) -0.0011(5) N004 0.0196(7) 0.0235(8) 0.0255(8) 0.0033(5) -0.0011(6) -0.0017(5) N005 0.0202(7) 0.0246(8) 0.0217(7) -0.0005(5) -0.0012(6) 0.0020(5) N006 0.0222(8) 0.0227(8) 0.0300(8) -0.0007(6) -0.0028(6) -0.0002(5) N007 0.0267(8) 0.0231(8) 0.0267(8) 0.0019(6) 0.0015(6) -0.0002(5) C008 0.0211(9) 0.0180(8) 0.0266(9) -0.0018(6) -0.0003(7) 0.0018(6) C009 0.0203(8) 0.0216(8) 0.0272(9) 0.0014(6) -0.0009(7) -0.0007(6) C00A 0.0227(9) 0.0209(8) 0.0245(8) 0.0017(6) -0.0020(7) 0.0007(6) C00B 0.0193(8) 0.0196(8) 0.0284(9) -0.0012(6) -0.0002(7) -0.0029(6) C00C 0.0238(9) 0.0185(8) 0.0283(9) -0.0003(6) -0.0023(7) -0.0034(6) C00D 0.0292(9) 0.0228(9) 0.0325(9) 0.0051(7) 0.0019(8) 0.0021(7) C00E 0.0216(8) 0.0242(9) 0.0278(9) -0.0003(7) 0.0000(7) 0.0008(6) C00F 0.0230(9) 0.0226(9) 0.0392(10) 0.0013(7) 0.0047(7) -0.0006(6) C00G 0.0319(10) 0.0223(9) 0.0364(10) -0.0051(7) 0.0065(8) -0.0025(7) C00H 0.0334(10) 0.0243(9) 0.0266(9) 0.0004(7) 0.0044(7) -0.0023(7) C00I 0.0195(8) 0.0252(9) 0.0374(10) -0.0006(7) -0.0023(7) 0.0002(6) C00J 0.0258(9) 0.0301(9) 0.0267(9) 0.0051(7) -0.0005(7) -0.0020(7) C00K 0.0283(9) 0.0244(9) 0.0304(9) -0.0020(7) -0.0034(7) 0.0004(7) C00L 0.0220(9) 0.0304(10) 0.0318(9) 0.0000(7) -0.0032(7) 0.0038(7) C00M 0.0248(9) 0.0270(10) 0.0405(11) -0.0044(8) 0.0006(8) 0.0016(7) 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 5 -3 -5 0.0903 -2 4 6 0.0953 -6 3 4 0.1049 -7 0 0 0.1163 0 -4 -6 0.0836 7 1 1 0.0857 0 5 -5 0.0418 -7 -1 -1 0.1125 -1 -5 5 0.0343 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 C00A N002 N004 118.91(14) . . ? C009 N003 N005 118.40(14) . . ? N002 N004 C00B 117.09(14) . . ? N002 N004 C00J 121.11(13) . . ? C00B N004 C00J 118.18(15) . . ? N003 N005 C00B 119.08(13) . . ? N003 N005 C00L 122.44(14) . . ? C00B N005 C00L 118.37(15) . . ? C008 N006 C00I 116.95(16) . . ? C00H N007 C00C 117.16(15) . . ? N006 C008 C00A 114.99(15) . . ? N006 C008 C00E 122.77(16) . . ? C00E C008 C00A 122.24(15) . . ? N003 C009 H009 120.3 . . ? N003 C009 C00C 119.30(15) . . ? C00C C009 H009 120.3 . . ? N002 C00A C008 118.18(15) . . ? N002 C00A H00A 120.9 . . ? C008 C00A H00A 120.9 . . ? O001 C00B N004 120.45(16) . . ? O001 C00B N005 121.58(15) . . ? N005 C00B N004 117.97(15) . . ? N007 C00C C009 114.76(15) . . ? N007 C00C C00K 122.51(17) . . ? C00K C00C C009 122.72(16) . . ? C00E C00D H00D 120.5 . . ? C00E C00D C00F 118.98(17) . . ? C00F C00D H00D 120.5 . . ? C008 C00E H00E 120.6 . . ? C00D C00E C008 118.88(15) . . ? C00D C00E H00E 120.6 . . ? C00D C00F H00F 120.8 . . ? C00I C00F C00D 118.39(17) . . ? C00I C00F H00F 120.8 . . ? C00H C00G H00G 121.1 . . ? C00H C00G C00M 117.87(18) . . ? C00M C00G H00G 121.1 . . ? N007 C00H C00G 124.38(17) . . ? N007 C00H H00H 117.8 . . ? C00G C00H H00H 117.8 . . ? N006 C00I C00F 123.92(16) . . ? N006 C00I H00I 118.0 . . ? C00F C00I H00I 118.0 . . ? N004 C00J H00B 109.5 . . ? N004 C00J H00C 109.5 . . ? N004 C00J H00J 109.5 . . ? H00B C00J H00C 109.5 . . ? H00B C00J H00J 109.5 . . ? H00C C00J H00J 109.5 . . ? C00C C00K H00K 120.5 . . ? C00M C00K C00C 118.95(18) . . ? C00M C00K H00K 120.5 . . ? N005 C00L H00L 109.5 . . ? N005 C00L H00M 109.5 . . ? N005 C00L H00N 109.5 . . ? H00L C00L H00M 109.5 . . ? H00L C00L H00N 109.5 . . ? H00M C00L H00N 109.5 . . ? C00G C00M H00O 120.4 . . ? C00K C00M C00G 119.12(18) . . ? C00K C00M H00O 120.4 . . ? 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 O001 C00B 1.230(2) . ? N002 N004 1.369(2) . ? N002 C00A 1.282(2) . ? N003 N005 1.366(2) . ? N003 C009 1.287(2) . ? N004 C00B 1.398(2) . ? N004 C00J 1.452(2) . ? N005 C00B 1.376(2) . ? N005 C00L 1.457(2) . ? N006 C008 1.344(2) . ? N006 C00I 1.344(2) . ? N007 C00C 1.347(2) . ? N007 C00H 1.335(2) . ? C008 C00A 1.475(2) . ? C008 C00E 1.395(2) . ? C009 H009 0.9300 . ? C009 C00C 1.464(3) . ? C00A H00A 0.9300 . ? C00C C00K 1.398(3) . ? C00D H00D 0.9300 . ? C00D C00E 1.381(3) . ? C00D C00F 1.383(3) . ? C00E H00E 0.9300 . ? C00F H00F 0.9300 . ? C00F C00I 1.381(3) . ? C00G H00G 0.9300 . ? C00G C00H 1.385(3) . ? C00G C00M 1.388(3) . ? C00H H00H 0.9300 . ? C00I H00I 0.9300 . ? C00J H00B 0.9600 . ? C00J H00C 0.9600 . ? C00J H00J 0.9600 . ? C00K H00K 0.9300 . ? C00K C00M 1.380(3) . ? C00L H00L 0.9600 . ? C00L H00M 0.9600 . ? C00L H00N 0.9600 . ? C00M H00O 0.9300 . ? 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 N002 N004 C00B O001 148.83(16) . . . . ? N002 N004 C00B N005 -31.8(2) . . . . ? N003 N005 C00B O001 154.24(16) . . . . ? N003 N005 C00B N004 -25.1(2) . . . . ? N003 C009 C00C N007 -170.69(15) . . . . ? N003 C009 C00C C00K 10.4(3) . . . . ? N004 N002 C00A C008 179.43(14) . . . . ? N005 N003 C009 C00C -178.69(13) . . . . ? N006 C008 C00A N002 -169.48(16) . . . . ? N006 C008 C00E C00D 2.9(3) . . . . ? N007 C00C C00K C00M 1.0(3) . . . . ? C008 N006 C00I C00F -0.3(3) . . . . ? C009 N003 N005 C00B -177.28(15) . . . . ? C009 N003 N005 C00L -1.2(2) . . . . ? C009 C00C C00K C00M 179.91(16) . . . . ? C00A N002 N004 C00B -166.27(16) . . . . ? C00A N002 N004 C00J -8.1(2) . . . . ? C00A C008 C00E C00D -176.60(16) . . . . ? C00C N007 C00H C00G -0.8(3) . . . . ? C00C C00K C00M C00G -1.2(3) . . . . ? C00D C00F C00I N006 2.9(3) . . . . ? C00E C008 C00A N002 10.0(2) . . . . ? C00E C00D C00F C00I -2.5(3) . . . . ? C00F C00D C00E C008 -0.1(3) . . . . ? C00H N007 C00C C009 -179.03(15) . . . . ? C00H N007 C00C C00K -0.1(3) . . . . ? C00H C00G C00M C00K 0.4(3) . . . . ? C00I N006 C008 C00A 176.86(15) . . . . ? C00I N006 C008 C00E -2.7(2) . . . . ? C00J N004 C00B O001 -10.0(2) . . . . ? C00J N004 C00B N005 169.34(15) . . . . ? C00L N005 C00B O001 -22.0(2) . . . . ? C00L N005 C00B N004 158.72(15) . . . . ? C00M C00G C00H N007 0.6(3) . . . . ? 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 4.9586 -3.4823 -5.0628 -0.4847 0.7924 -0.3702 -1.9602 4.2178 6.1596 0.5201 -0.8495 -0.0888 -6.0726 2.8303 4.1010 0.4278 -0.6998 0.5721 -7.2930 -0.1252 -0.2328 0.1063 -0.1752 0.9788 -0.1719 -4.2188 -6.1756 -0.4849 0.7915 0.3720 6.9426 1.2919 1.2131 0.0486 0.0307 -0.9983 0.4853 5.2658 -5.0680 0.8523 0.5217 0.0364 -6.9476 -1.3858 -1.1214 -0.0639 -0.0401 0.9972 -1.1814 -5.3580 4.9092 -0.8511 -0.5210 0.0645