#------------------------------------------------------------------------------ #$Date: 2020-02-04 22:05:45 +0200 (Tue, 04 Feb 2020) $ #$Revision: 247599 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125649.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_7125649 loop_ _publ_author_name 'Bousfiha, Asmae' 'Dim\'e, Abdou K D' 'Mankou-Makaya, Amelle' 'Echaubard, Julie' 'Berthelot, Mathieu' 'Cattey, H\'el\`ene' 'Romieu, Anthony' 'Roger, Julien' 'Devillers, Charles H.' _publ_section_title ; Regioselective C-H amination of free base porphyrins via electrogenerated pyridinium-porphyrins and stabilization of easily oxidized amino-porphyrins by protonation. ; _journal_issue 6 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 884 _journal_page_last 887 _journal_paper_doi 10.1039/c9cc07351e _journal_volume 56 _journal_year 2020 _chemical_formula_moiety 'C44 H31 N5' _chemical_formula_sum 'C44 H31 N5' _chemical_formula_weight 629.74 _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' _symmetry_space_group_name_Hall '-P 2ybc' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2019-06-07 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-09-09 deposited with the CCDC. 2019-12-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 114.209(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 14.7683(9) _cell_length_b 9.6009(5) _cell_length_c 12.4544(7) _cell_measurement_reflns_used 9858 _cell_measurement_temperature 100.01 _cell_measurement_theta_max 27.44 _cell_measurement_theta_min 3.02 _cell_volume 1610.60(16) _computing_cell_refinement 'SAINT V8.38A (Bruker, 2016)' _computing_data_collection 'APEX3 (Bruker, 2015)' _computing_data_reduction 'SAINT V8.38A (Bruker, 2016)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 100.01 _diffrn_detector CMOS _diffrn_detector_area_resol_mean '1024 x 1024' _diffrn_detector_type 'Photon 100' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device '\k-geometry diffractometer triump Mo' _diffrn_measurement_device_type 'Bruker D8 Venture triumph Mo' _diffrn_measurement_method '\f and \w scans'' _diffrn_radiation_collimation '0.6 mm' _diffrn_radiation_monochromator 'TRIUMPH curved crystal' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0520 _diffrn_reflns_av_unetI/netI 0.0261 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 39621 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.603 _diffrn_reflns_theta_min 3.025 _diffrn_source 'X-ray tube' _diffrn_source_target Mo _diffrn_source_type 'Siemens KFF Mo 2K-90C' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6253 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0756 before and 0.0645 after correction. The Ratio of minimum to maximum transmission is 0.8387.' _exptl_crystal_colour 'clear light violet' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary violet _exptl_crystal_density_diffrn 1.299 _exptl_crystal_description prism _exptl_crystal_F_000 660 _exptl_crystal_recrystallization_method 'The material was recrystallised from a mixture of DCM and ether by slow evaporation' _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.19 _refine_diff_density_max 0.641 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.057 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 226 _refine_ls_number_reflns 3712 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.060 _refine_ls_R_factor_all 0.0753 _refine_ls_R_factor_gt 0.0517 _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^)+(0.0560P)^2^+1.4297P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1215 _refine_ls_wR_factor_ref 0.1423 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2840 _reflns_number_total 3712 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc07351e2.cif _cod_data_source_block H2TPP-NH2 _cod_depositor_comments 'Adding full bibliography for 7125649--7125650.cif.' _cod_database_code 7125649 _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 0.985 _shelx_estimated_absorpt_t_min 0.974 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups, All N(H,H) groups 2. Others Fixed Sof: H2(0.5) N3(0.5) H3A(0.5) H3B(0.5) 3.a Aromatic/amide H refined with riding coordinates: N1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22) 3.b X=CH2 refined with riding coordinates: N3(H3A,H3B) ; _shelx_res_file ; TITL 1905cd86_0ma_a.res in P2(1)/c 1905cd86_0ma_a.res created by SHELXL-2018/3 at 14:52:05 on 07-Jun-2019 REM Old TITL 1905cd86_0ma in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.138, Rweak 0.003, Alpha 0.023, Orientation as input CELL 0.71073 14.7683 9.6009 12.4544 90 114.209 90 ZERR 2 0.0009 0.0005 0.0007 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N UNIT 88 62 10 L.S. 10 PLAN 20 SIZE 0.34 0.3 0.19 TEMP -173.14 BOND $H LIST 4 CONF fmap 2 acta REM REM REM WGHT 0.056000 1.429700 FVAR 0.58839 C1 1 0.481005 0.385153 0.723415 11.00000 0.02444 0.02215 = 0.02057 -0.00019 0.01270 0.00077 N1 3 0.544265 0.414664 0.670312 11.00000 0.02118 0.02672 = 0.01999 0.00502 0.00999 0.00318 AFIX 43 H1 2 0.526996 0.457788 0.602429 11.00000 -1.20000 AFIX 0 C2 1 0.539285 0.313131 0.831335 11.00000 0.02486 0.02328 = 0.02158 0.00108 0.01103 -0.00034 PART 2 AFIX 43 H2 2 0.515941 0.278772 0.886913 10.50000 -1.20000 AFIX 0 PART 0 N2 3 0.640694 0.485260 0.514992 11.00000 0.02203 0.02267 = 0.02001 0.00058 0.00977 0.00090 C3 1 0.634105 0.303140 0.839364 11.00000 0.02193 0.02378 = 0.02292 0.00223 0.00880 0.00106 AFIX 43 H3 2 0.688286 0.260566 0.901870 11.00000 -1.20000 AFIX 0 PART 1 N3 3 0.509154 0.262475 0.913971 10.50000 0.02717 0.03954 = 0.02843 0.00821 0.01494 0.00543 AFIX 93 H3A 2 0.551975 0.220341 0.977134 10.50000 -1.20000 H3B 2 0.446939 0.272005 0.903995 10.50000 -1.20000 AFIX 0 PART 0 C4 1 0.638103 0.367167 0.738452 11.00000 0.02310 0.02194 = 0.02288 0.00078 0.01012 0.00155 C5 1 0.721220 0.375301 0.711212 11.00000 0.02229 0.02311 = 0.02203 0.00080 0.01046 0.00190 C6 1 0.721070 0.430145 0.606917 11.00000 0.02114 0.02120 = 0.02236 -0.00081 0.00928 -0.00120 C7 1 0.808959 0.434607 0.581751 11.00000 0.02067 0.02429 = 0.02449 -0.00116 0.00959 0.00019 AFIX 43 H7 2 0.873672 0.403142 0.631434 11.00000 -1.20000 AFIX 0 C8 1 0.780637 0.491887 0.474604 11.00000 0.02135 0.02338 = 0.02351 -0.00144 0.01130 -0.00156 AFIX 43 H8 2 0.821479 0.508200 0.433560 11.00000 -1.20000 AFIX 0 C9 1 0.675731 0.524198 0.433308 11.00000 0.02310 0.02084 = 0.01959 -0.00261 0.01007 -0.00262 C10 1 0.620105 0.584197 0.322488 11.00000 0.02330 0.02130 = 0.02028 -0.00231 0.01148 -0.00136 C11 1 0.816873 0.321469 0.802486 11.00000 0.02138 0.02835 = 0.02549 0.00743 0.01202 0.00151 C12 1 0.864153 0.206789 0.779409 11.00000 0.02777 0.03298 = 0.03410 0.00813 0.01640 0.00572 AFIX 43 H12 2 0.835571 0.162212 0.704832 11.00000 -1.20000 AFIX 0 C13 1 0.953238 0.157257 0.865372 11.00000 0.02968 0.04002 = 0.05106 0.01485 0.02221 0.01012 AFIX 43 H13 2 0.985484 0.079888 0.848726 11.00000 -1.20000 AFIX 0 C14 1 0.994580 0.220167 0.974287 11.00000 0.02012 0.05067 = 0.04038 0.02037 0.00853 0.00331 AFIX 43 H14 2 1.054896 0.185638 1.032852 11.00000 -1.20000 AFIX 0 C15 1 0.948244 0.333531 0.998275 11.00000 0.02620 0.04640 = 0.03007 0.00802 0.00641 -0.00593 AFIX 43 H15 2 0.976584 0.376736 1.073453 11.00000 -1.20000 AFIX 0 C16 1 0.860270 0.384306 0.912521 11.00000 0.02493 0.03230 = 0.02812 0.00405 0.01048 0.00021 AFIX 43 H16 2 0.829318 0.463062 0.929281 11.00000 -1.20000 AFIX 0 C17 1 0.674164 0.615490 0.246774 11.00000 0.02183 0.02568 = 0.02051 0.00083 0.00996 0.00208 C18 1 0.655748 0.538862 0.145573 11.00000 0.04060 0.04167 = 0.03281 -0.01203 0.02231 -0.01352 AFIX 43 H18 2 0.607725 0.466411 0.123502 11.00000 -1.20000 AFIX 0 C19 1 0.706979 0.567251 0.076271 11.00000 0.05276 0.05377 = 0.03562 -0.01356 0.03027 -0.01070 AFIX 43 H19 2 0.692494 0.515947 0.005913 11.00000 -1.20000 AFIX 0 C20 1 0.779043 0.669928 0.109202 11.00000 0.03533 0.04645 = 0.03035 0.00663 0.02116 0.00199 AFIX 43 H20 2 0.815382 0.687323 0.062887 11.00000 -1.20000 AFIX 0 C21 1 0.797808 0.746755 0.209448 11.00000 0.02505 0.03614 = 0.02751 0.00620 0.00956 -0.00475 AFIX 43 H21 2 0.847099 0.817513 0.232310 11.00000 -1.20000 AFIX 0 C22 1 0.745017 0.721048 0.276848 11.00000 0.02813 0.02746 = 0.02054 0.00151 0.00922 -0.00044 AFIX 43 H22 2 0.757233 0.776203 0.344724 11.00000 -1.20000 AFIX 0 HKLF 4 REM 1905cd86_0ma_a.res in P2(1)/c REM wR2 = 0.142319, GooF = S = 1.05969, Restrained GooF = 1.05969 for all data REM R1 = 0.051741 for 2840 Fo > 4sig(Fo) and 0.075319 for all 3712 data REM 226 parameters refined using 0 restraints END WGHT 0.0560 1.4296 REM Highest difference peak 0.641, deepest hole -0.279, 1-sigma level 0.057 Q1 1 0.5000 0.5000 0.5000 10.50000 0.05 0.64 Q2 1 0.8348 0.4602 0.4070 11.00000 0.05 0.23 Q3 1 0.5092 0.3454 0.5480 11.00000 0.05 0.21 Q4 1 0.9256 0.5060 0.6909 11.00000 0.05 0.21 Q5 1 0.6771 0.3368 0.7009 11.00000 0.05 0.21 Q6 1 0.7385 0.2883 1.0317 11.00000 0.05 0.20 Q7 1 0.7207 0.6439 0.2804 11.00000 0.05 0.20 Q8 1 0.6294 0.5182 0.3623 11.00000 0.05 0.19 Q9 1 0.7022 0.3122 0.9569 11.00000 0.05 0.19 Q10 1 0.7712 0.5868 0.1216 11.00000 0.05 0.19 Q11 1 0.5937 0.5665 0.5271 11.00000 0.05 0.19 Q12 1 0.6847 0.7066 0.2427 11.00000 0.05 0.18 Q13 1 0.4423 0.4519 0.7216 11.00000 0.05 0.18 Q14 1 0.8276 0.2538 0.5582 11.00000 0.05 0.18 Q15 1 0.8992 0.5644 0.1147 11.00000 0.05 0.18 Q16 1 0.7197 0.2489 0.9502 11.00000 0.05 0.18 Q17 1 0.6403 0.6241 0.2711 11.00000 0.05 0.18 Q18 1 0.7223 0.6540 0.0719 11.00000 0.05 0.18 Q19 1 0.6777 0.5546 0.2222 11.00000 0.05 0.18 Q20 1 0.7709 0.4188 0.6077 11.00000 0.05 0.17 ; _shelx_res_checksum 58881 _olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems' _olex2_exptl_crystal_mounting_method 'The crystal was mounted on a mylar loop with oil' _olex2_submission_special_instructions 'No special instructions were received' 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_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.48101(13) 0.38515(18) 0.72342(15) 0.0212(4) Uani 1 1 d . . . . N1 N 0.54426(10) 0.41466(15) 0.67031(13) 0.0221(3) Uani 1 1 d . . . . H1 H 0.526996 0.457788 0.602429 0.027 Uiso 1 1 calc R . . . C2 C 0.53928(13) 0.31313(18) 0.83134(15) 0.0227(4) Uani 1 1 d . . . . H2 H 0.515941 0.278772 0.886913 0.027 Uiso 0.5 1 calc R P A 2 N2 N 0.64069(11) 0.48526(15) 0.51499(12) 0.0212(3) Uani 1 1 d . . . . C3 C 0.63410(13) 0.30314(18) 0.83936(15) 0.0230(4) Uani 1 1 d . . . . H3 H 0.688286 0.260566 0.901870 0.028 Uiso 1 1 calc R . . . N3 N 0.5092(2) 0.2625(4) 0.9140(3) 0.0306(7) Uani 0.5 1 d . P B 1 H3A H 0.551975 0.220341 0.977134 0.037 Uiso 0.5 1 calc R P B 1 H3B H 0.446939 0.272005 0.903995 0.037 Uiso 0.5 1 calc R P B 1 C4 C 0.63810(13) 0.36717(18) 0.73845(15) 0.0224(4) Uani 1 1 d . . . . C5 C 0.72122(13) 0.37530(18) 0.71121(15) 0.0220(4) Uani 1 1 d . . . . C6 C 0.72107(13) 0.43014(18) 0.60692(15) 0.0214(4) Uani 1 1 d . . . . C7 C 0.80896(13) 0.43461(18) 0.58175(15) 0.0230(4) Uani 1 1 d . . . . H7 H 0.873672 0.403142 0.631434 0.028 Uiso 1 1 calc R . . . C8 C 0.78064(13) 0.49189(18) 0.47460(15) 0.0221(4) Uani 1 1 d . . . . H8 H 0.821479 0.508200 0.433560 0.026 Uiso 1 1 calc R . . . C9 C 0.67573(13) 0.52420(17) 0.43331(15) 0.0207(4) Uani 1 1 d . . . . C10 C 0.62011(13) 0.58420(17) 0.32249(15) 0.0208(4) Uani 1 1 d . . . . C11 C 0.81687(13) 0.32147(19) 0.80249(16) 0.0243(4) Uani 1 1 d . . . . C12 C 0.86415(14) 0.2068(2) 0.77941(18) 0.0304(4) Uani 1 1 d . . . . H12 H 0.835571 0.162212 0.704832 0.036 Uiso 1 1 calc R . . . C13 C 0.95324(15) 0.1573(2) 0.8654(2) 0.0384(5) Uani 1 1 d . . . . H13 H 0.985484 0.079888 0.848726 0.046 Uiso 1 1 calc R . . . C14 C 0.99458(15) 0.2202(2) 0.97429(19) 0.0383(5) Uani 1 1 d . . . . H14 H 1.054896 0.185638 1.032852 0.046 Uiso 1 1 calc R . . . C15 C 0.94824(14) 0.3335(2) 0.99827(18) 0.0359(5) Uani 1 1 d . . . . H15 H 0.976584 0.376736 1.073453 0.043 Uiso 1 1 calc R . . . C16 C 0.86027(14) 0.3843(2) 0.91252(17) 0.0286(4) Uani 1 1 d . . . . H16 H 0.829318 0.463062 0.929281 0.034 Uiso 1 1 calc R . . . C17 C 0.67416(13) 0.61549(18) 0.24677(15) 0.0223(4) Uani 1 1 d . . . . C18 C 0.65575(16) 0.5389(2) 0.14557(18) 0.0360(5) Uani 1 1 d . . . . H18 H 0.607725 0.466411 0.123502 0.043 Uiso 1 1 calc R . . . C19 C 0.70698(18) 0.5673(3) 0.0763(2) 0.0434(6) Uani 1 1 d . . . . H19 H 0.692494 0.515947 0.005913 0.052 Uiso 1 1 calc R . . . C20 C 0.77904(15) 0.6699(2) 0.10920(18) 0.0348(5) Uani 1 1 d . . . . H20 H 0.815382 0.687323 0.062887 0.042 Uiso 1 1 calc R . . . C21 C 0.79781(14) 0.7468(2) 0.20945(17) 0.0300(4) Uani 1 1 d . . . . H21 H 0.847099 0.817513 0.232310 0.036 Uiso 1 1 calc R . . . C22 C 0.74502(13) 0.72105(19) 0.27685(16) 0.0256(4) Uani 1 1 d . . . . H22 H 0.757233 0.776203 0.344724 0.031 Uiso 1 1 calc R . . . 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 C1 0.0244(9) 0.0221(8) 0.0206(8) -0.0002(6) 0.0127(7) 0.0008(7) N1 0.0212(7) 0.0267(8) 0.0200(7) 0.0050(6) 0.0100(6) 0.0032(6) C2 0.0249(9) 0.0233(8) 0.0216(8) 0.0011(7) 0.0110(7) -0.0003(7) N2 0.0220(7) 0.0227(7) 0.0200(7) 0.0006(6) 0.0098(6) 0.0009(5) C3 0.0219(8) 0.0238(8) 0.0229(8) 0.0022(7) 0.0088(7) 0.0011(7) N3 0.0272(16) 0.0395(18) 0.0284(16) 0.0082(14) 0.0149(14) 0.0054(13) C4 0.0231(9) 0.0219(8) 0.0229(8) 0.0008(7) 0.0101(7) 0.0016(7) C5 0.0223(9) 0.0231(8) 0.0220(8) 0.0008(7) 0.0105(7) 0.0019(7) C6 0.0211(8) 0.0212(8) 0.0224(8) -0.0008(7) 0.0093(7) -0.0012(6) C7 0.0207(8) 0.0243(9) 0.0245(9) -0.0012(7) 0.0096(7) 0.0002(7) C8 0.0213(8) 0.0234(8) 0.0235(8) -0.0014(7) 0.0113(7) -0.0016(6) C9 0.0231(8) 0.0208(8) 0.0196(8) -0.0026(6) 0.0101(7) -0.0026(6) C10 0.0233(8) 0.0213(8) 0.0203(8) -0.0023(6) 0.0115(7) -0.0014(6) C11 0.0214(8) 0.0284(9) 0.0255(9) 0.0074(7) 0.0120(7) 0.0015(7) C12 0.0278(9) 0.0330(10) 0.0341(10) 0.0081(8) 0.0164(8) 0.0057(8) C13 0.0297(10) 0.0400(11) 0.0511(13) 0.0149(10) 0.0222(10) 0.0101(9) C14 0.0201(9) 0.0507(13) 0.0404(12) 0.0204(10) 0.0085(8) 0.0033(9) C15 0.0262(10) 0.0464(12) 0.0301(10) 0.0080(9) 0.0064(8) -0.0059(9) C16 0.0249(9) 0.0323(10) 0.0281(9) 0.0040(8) 0.0105(8) 0.0002(7) C17 0.0218(8) 0.0257(9) 0.0205(8) 0.0008(7) 0.0100(7) 0.0021(7) C18 0.0406(11) 0.0417(12) 0.0328(10) -0.0120(9) 0.0223(9) -0.0135(9) C19 0.0528(14) 0.0538(14) 0.0356(11) -0.0136(10) 0.0303(11) -0.0107(11) C20 0.0353(11) 0.0465(12) 0.0304(10) 0.0066(9) 0.0212(9) 0.0020(9) C21 0.0250(9) 0.0361(10) 0.0275(9) 0.0062(8) 0.0096(8) -0.0048(8) C22 0.0281(9) 0.0275(9) 0.0205(8) 0.0015(7) 0.0092(7) -0.0004(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 '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 N1 C1 C2 106.45(14) . . N1 C1 C10 125.67(15) . 3_666 C10 C1 C2 127.84(16) 3_666 . C1 N1 H1 124.9 . . C4 N1 C1 110.27(14) . . C4 N1 H1 124.9 . . C1 C2 H2 126.1 . . C3 C2 C1 107.72(15) . . C3 C2 H2 126.1 . . C3 C2 N3 124.1(2) . . N3 C2 C1 128.2(2) . . C9 N2 C6 105.30(14) . . C2 C3 H3 125.7 . . C2 C3 C4 108.53(15) . . C4 C3 H3 125.7 . . C2 N3 H3A 120.0 . . C2 N3 H3B 120.0 . . H3A N3 H3B 120.0 . . N1 C4 C3 107.02(15) . . N1 C4 C5 126.40(16) . . C5 C4 C3 126.53(16) . . C4 C5 C11 116.37(15) . . C6 C5 C4 125.18(16) . . C6 C5 C11 118.45(15) . . N2 C6 C5 126.17(16) . . N2 C6 C7 110.58(15) . . C5 C6 C7 123.25(16) . . C6 C7 H7 126.7 . . C8 C7 C6 106.52(15) . . C8 C7 H7 126.7 . . C7 C8 H8 126.5 . . C7 C8 C9 106.98(15) . . C9 C8 H8 126.5 . . N2 C9 C8 110.61(15) . . N2 C9 C10 126.43(16) . . C10 C9 C8 122.94(15) . . C1 C10 C9 125.79(16) 3_666 . C1 C10 C17 117.28(15) 3_666 . C9 C10 C17 116.93(15) . . C12 C11 C5 120.83(17) . . C16 C11 C5 120.61(16) . . C16 C11 C12 118.56(17) . . C11 C12 H12 119.8 . . C11 C12 C13 120.3(2) . . C13 C12 H12 119.8 . . C12 C13 H13 119.9 . . C14 C13 C12 120.2(2) . . C14 C13 H13 119.9 . . C13 C14 H14 120.0 . . C13 C14 C15 119.95(19) . . C15 C14 H14 120.0 . . C14 C15 H15 120.0 . . C14 C15 C16 120.0(2) . . C16 C15 H15 120.0 . . C11 C16 H16 119.5 . . C15 C16 C11 120.90(19) . . C15 C16 H16 119.5 . . C18 C17 C10 120.69(16) . . C18 C17 C22 118.43(17) . . C22 C17 C10 120.88(15) . . C17 C18 H18 119.8 . . C17 C18 C19 120.48(19) . . C19 C18 H18 119.8 . . C18 C19 H19 119.8 . . C20 C19 C18 120.31(19) . . C20 C19 H19 119.8 . . C19 C20 H20 120.2 . . C21 C20 C19 119.65(18) . . C21 C20 H20 120.2 . . C20 C21 H21 120.0 . . C20 C21 C22 120.08(18) . . C22 C21 H21 120.0 . . C17 C22 H22 119.5 . . C21 C22 C17 121.01(17) . . C21 C22 H22 119.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 N1 1.377(2) . C1 C2 1.441(2) . C1 C10 1.394(2) 3_666 N1 H1 0.8800 . N1 C4 1.373(2) . C2 H2 0.9500 . C2 C3 1.366(2) . C2 N3 1.367(3) . N2 C6 1.373(2) . N2 C9 1.369(2) . C3 H3 0.9500 . C3 C4 1.422(2) . N3 H3A 0.8800 . N3 H3B 0.8800 . C4 C5 1.403(2) . C5 C6 1.401(2) . C5 C11 1.496(2) . C6 C7 1.455(2) . C7 H7 0.9500 . C7 C8 1.342(2) . C8 H8 0.9500 . C8 C9 1.452(2) . C9 C10 1.408(2) . C10 C17 1.495(2) . C11 C12 1.395(3) . C11 C16 1.390(3) . C12 H12 0.9500 . C12 C13 1.396(3) . C13 H13 0.9500 . C13 C14 1.378(3) . C14 H14 0.9500 . C14 C15 1.382(3) . C15 H15 0.9500 . C15 C16 1.389(3) . C16 H16 0.9500 . C17 C18 1.387(3) . C17 C22 1.393(2) . C18 H18 0.9500 . C18 C19 1.388(3) . C19 H19 0.9500 . C19 C20 1.384(3) . C20 H20 0.9500 . C20 C21 1.377(3) . C21 H21 0.9500 . C21 C22 1.382(3) . C22 H22 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_4 C1 N1 C4 C3 0.6(2) . . C1 N1 C4 C5 178.19(17) . . C1 C2 C3 C4 -0.1(2) . . C1 C10 C17 C18 -69.1(2) 3_666 . C1 C10 C17 C22 111.67(19) 3_666 . N1 C1 C2 C3 0.44(19) . . N1 C1 C2 N3 -179.9(2) . . N1 C4 C5 C6 -2.1(3) . . N1 C4 C5 C11 177.41(17) . . C2 C1 N1 C4 -0.62(19) . . C2 C3 C4 N1 -0.3(2) . . C2 C3 C4 C5 -177.90(17) . . N2 C6 C7 C8 -0.2(2) . . N2 C9 C10 C1 0.2(3) . 3_666 N2 C9 C10 C17 -178.76(16) . . C3 C4 C5 C6 175.08(17) . . C3 C4 C5 C11 -5.4(3) . . N3 C2 C3 C4 -179.8(2) . . C4 C5 C6 N2 0.4(3) . . C4 C5 C6 C7 -179.09(16) . . C4 C5 C11 C12 116.18(19) . . C4 C5 C11 C16 -63.4(2) . . C5 C6 C7 C8 179.28(17) . . C5 C11 C12 C13 -179.82(17) . . C5 C11 C16 C15 178.99(17) . . C6 N2 C9 C8 0.39(18) . . C6 N2 C9 C10 178.88(16) . . C6 C5 C11 C12 -64.3(2) . . C6 C5 C11 C16 116.1(2) . . C6 C7 C8 C9 0.47(19) . . C7 C8 C9 N2 -0.6(2) . . C7 C8 C9 C10 -179.11(16) . . C8 C9 C10 C1 178.48(16) . 3_666 C8 C9 C10 C17 -0.4(2) . . C9 N2 C6 C5 -179.61(17) . . C9 N2 C6 C7 -0.10(19) . . C9 C10 C17 C18 109.9(2) . . C9 C10 C17 C22 -69.3(2) . . C10 C1 N1 C4 -178.54(17) 3_666 . C10 C1 C2 C3 178.30(17) 3_666 . C10 C1 C2 N3 -2.0(3) 3_666 . C10 C17 C18 C19 -179.2(2) . . C10 C17 C22 C21 177.53(17) . . C11 C5 C6 N2 -179.16(16) . . C11 C5 C6 C7 1.4(3) . . C11 C12 C13 C14 0.8(3) . . C12 C11 C16 C15 -0.6(3) . . C12 C13 C14 C15 -0.6(3) . . C13 C14 C15 C16 -0.2(3) . . C14 C15 C16 C11 0.9(3) . . C16 C11 C12 C13 -0.2(3) . . C17 C18 C19 C20 1.8(4) . . C18 C17 C22 C21 -1.7(3) . . C18 C19 C20 C21 -1.9(4) . . C19 C20 C21 C22 0.2(3) . . C20 C21 C22 C17 1.7(3) . . C22 C17 C18 C19 0.0(3) . .