#------------------------------------------------------------------------------ #$Date: 2023-11-02 01:35:29 +0200 (Thu, 02 Nov 2023) $ #$Revision: 287226 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247616.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_7247616 loop_ _publ_author_name 'Baig, K. Mohamed Yusuf' 'Kole, Goutam Kumar' _publ_section_title ; Silver(i) coordination polymers of trans-5-styrylpyrimidine -- from structural diversity to solid-state reactivity under sunlight ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D3CE00756A _journal_year 2023 _chemical_formula_sum 'C12 H10 N2' _chemical_formula_weight 182.18 _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 difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2023-06-23 deposited with the CCDC. 2023-10-09 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.989(2) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 22.3235(11) _cell_length_b 11.7383(5) _cell_length_c 7.5580(4) _cell_measurement_reflns_used 9914 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 27.11 _cell_measurement_theta_min 2.74 _cell_volume 1977.80(17) _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_unetI/netI 0.0284 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 24051 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.371 _diffrn_reflns_theta_min 1.961 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_T_max 0.7455 _exptl_absorpt_correction_T_min 0.6082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SadAbs 2016/2 (Bruker AXS)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.224 _exptl_crystal_description block _exptl_crystal_F_000 768 _exptl_crystal_size_max 0.330 _exptl_crystal_size_mid 0.270 _exptl_crystal_size_min 0.240 _refine_diff_density_max 0.143 _refine_diff_density_min -0.129 _refine_diff_density_rms 0.025 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 254 _refine_ls_number_reflns 4041 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.064 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0433 _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^)+(0.0553P)^2^+0.2817P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1181 _refine_ls_wR_factor_ref 0.1273 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3298 _reflns_number_total 4041 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00756a2.cif _cod_data_source_block YB-79 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7247616 _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_min 0.976 _shelx_estimated_absorpt_t_max 0.982 _shelx_res_file ; TITL YB-79_a.res in P2(1)/c YB-79.res created by SHELXL-2018/3 at 10:27:17 on 15-Feb-2023 CELL 0.71073 22.3235 11.7383 7.5580 90.000 92.989 90.000 ZERR 8.00 0.0011 0.0005 0.0004 0.000 0.002 0.000 LATT 1 SYMM -x, y+1/2, -z+1/2 SFAC C H N UNIT 95.9824 79.9868 15.9912 LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!! TEMP 22.0 SIZE 0.240 0.270 0.330 ACTA SHEL 999. 0.8 L.S. 4 FMAP 2 PLAN -5 0 0.00 HTAB BOND $H CONF WGHT 0.055300 0.281700 FVAR 0.79907 0.00066 N1 3 0.549760 0.475345 0.696915 11.00000 0.05273 0.05574 = 0.08507 -0.00294 0.01435 0.00427 C1 1 0.563735 0.583634 0.673393 11.00000 0.05357 0.06038 = 0.08600 -0.00881 0.01494 -0.00724 AFIX 43 H1 2 0.602017 0.598240 0.635973 11.00000 -1.20000 AFIX 0 C2 1 0.495092 0.456871 0.751389 11.00000 0.05741 0.04202 = 0.07161 0.00079 0.01035 0.00174 AFIX 43 H2 2 0.483577 0.381861 0.770006 11.00000 -1.20000 AFIX 0 N2 3 0.529465 0.672898 0.697088 11.00000 0.06580 0.04824 = 0.11615 -0.00649 0.02598 -0.01088 C3 1 0.454203 0.541784 0.782220 11.00000 0.04976 0.04127 = 0.05216 -0.00239 0.00325 -0.00032 C5 1 0.393657 0.521557 0.839402 11.00000 0.04946 0.04165 = 0.06042 -0.00125 0.00607 0.00481 AFIX 43 H5 2 0.367701 0.583574 0.836800 11.00000 -1.20000 AFIX 0 C4 1 0.474823 0.650335 0.751430 11.00000 0.06170 0.04092 = 0.10163 -0.00425 0.02039 0.00096 AFIX 43 H4 2 0.449203 0.711224 0.769564 11.00000 -1.20000 AFIX 0 C9 1 0.240951 0.282240 1.094733 11.00000 0.07100 0.05447 = 0.05939 0.00838 0.00699 -0.01347 AFIX 43 H9 2 0.233296 0.216239 1.157770 11.00000 -1.20000 AFIX 0 C8 1 0.298072 0.303894 1.042412 11.00000 0.06139 0.04407 = 0.05736 0.00615 0.00156 0.00000 AFIX 43 H8 2 0.328522 0.251794 1.070046 11.00000 -1.20000 AFIX 0 C7 1 0.311075 0.402554 0.948725 11.00000 0.05092 0.04124 = 0.04426 -0.00167 0.00233 -0.00169 C6 1 0.372072 0.423096 0.894794 11.00000 0.05011 0.04423 = 0.05363 0.00202 0.00246 0.00477 AFIX 43 H6 2 0.398242 0.361399 0.899728 11.00000 -1.20000 AFIX 0 C12 1 0.263958 0.477821 0.907529 11.00000 0.05314 0.04165 = 0.05343 0.00206 0.00475 -0.00005 AFIX 43 H12 2 0.271203 0.543880 0.844160 11.00000 -1.20000 AFIX 0 C11 1 0.206942 0.455580 0.959423 11.00000 0.05125 0.05575 = 0.06333 -0.00311 0.00385 0.00265 AFIX 43 H11 2 0.176076 0.506587 0.930665 11.00000 -1.20000 AFIX 0 C10 1 0.195197 0.357911 1.054054 11.00000 0.05542 0.06842 = 0.06182 -0.00159 0.01104 -0.01363 AFIX 43 H10 2 0.156695 0.343511 1.089883 11.00000 -1.20000 AFIX 0 C17 1 0.104323 0.764653 0.632211 11.00000 0.04888 0.04671 = 0.05933 0.00417 0.00608 -0.00085 AFIX 43 H17 2 0.129028 0.828436 0.631774 11.00000 -1.20000 AFIX 0 C24 1 0.207583 0.548284 0.462139 11.00000 0.06448 0.04979 = 0.05943 -0.00459 0.00071 0.00674 AFIX 43 H24 2 0.178784 0.492423 0.437743 11.00000 -1.20000 AFIX 0 C23 1 0.265676 0.530598 0.414708 11.00000 0.07430 0.06037 = 0.06255 -0.00701 0.00648 0.02267 AFIX 43 H23 2 0.275573 0.463432 0.357862 11.00000 -1.20000 AFIX 0 C22 1 0.309109 0.611778 0.451007 11.00000 0.05727 0.07592 = 0.06113 0.00797 0.01291 0.02053 AFIX 43 H22 2 0.348199 0.600037 0.418117 11.00000 -1.20000 AFIX 0 C21 1 0.294018 0.710989 0.536898 11.00000 0.05266 0.06000 = 0.06393 0.00824 0.00601 0.00280 AFIX 43 H21 2 0.323250 0.765744 0.563190 11.00000 -1.20000 AFIX 0 C20 1 0.235962 0.729211 0.583747 11.00000 0.05331 0.04661 = 0.05412 0.00054 0.00552 0.00610 AFIX 43 H20 2 0.226459 0.796331 0.641347 11.00000 -1.20000 AFIX 0 C19 1 0.191319 0.648696 0.546181 11.00000 0.05301 0.04630 = 0.04342 0.00278 0.00240 0.00666 C18 1 0.129081 0.666114 0.591813 11.00000 0.05128 0.04846 = 0.05289 -0.00067 0.00188 -0.00160 AFIX 43 H18 2 0.104622 0.601998 0.592515 11.00000 -1.20000 AFIX 0 C13 1 -0.070061 0.824860 0.762271 -21.00000 0.04622 0.06830 = 0.10038 0.00753 0.01022 0.00668 AFIX 43 H13 2 -0.109311 0.839311 0.791351 -21.00000 -1.20000 AFIX 0 C14 1 0.020199 0.891949 0.697793 -21.00000 0.05500 0.04789 = 0.11094 0.00257 0.01510 -0.00005 AFIX 43 H14 2 0.045770 0.953095 0.680905 -21.00000 -1.20000 AFIX 0 C15 1 0.042368 0.783626 0.677318 -21.00000 0.04835 0.04754 = 0.05272 0.00417 0.00226 0.00208 C16 1 0.001520 0.698341 0.705106 -21.00000 0.05648 0.04783 = 0.08673 0.00588 0.01339 0.00179 AFIX 43 H16 2 0.014060 0.623274 0.693606 -21.00000 -1.20000 AFIX 0 N3 3 -0.054822 0.716817 0.747428 -21.00000 0.05191 0.06271 = 0.10200 0.00852 0.01569 -0.00217 N4 3 -0.035768 0.914353 0.740406 -21.00000 0.05762 0.05585 = 0.13569 0.00260 0.02068 0.01052 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM YB-79_a.res in P2(1)/c REM wR2 = 0.127295, GooF = S = 1.06368, Restrained GooF = 1.06368 for all data REM R1 = 0.043286 for 3298 Fo > 4sig(Fo) and 0.054143 for all 4041 data REM 254 parameters refined using 0 restraints END WGHT 0.0553 0.2816 REM Instructions for potential hydrogen bonds EQIV $1 -x+1, y-1/2, -z+3/2 HTAB C2 N2_$1 EQIV $2 -x, y-1/2, -z+3/2 HTAB C16 N4_$2 REM Highest difference peak 0.143, deepest hole -0.129, 1-sigma level 0.025 Q1 1 0.4682 0.5853 0.8214 11.00000 0.05 0.14 Q2 1 0.2933 0.4521 0.9754 11.00000 0.05 0.14 Q3 1 0.2116 0.2873 1.0107 11.00000 0.05 0.12 Q4 1 0.0706 0.7726 0.6836 11.00000 0.05 0.12 Q5 1 0.2013 0.5996 0.5189 11.00000 0.05 0.12 ; _shelx_res_checksum 28116 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 N1 N 0.54976(5) 0.47534(10) 0.69691(17) 0.0641(3) Uani 1 1 d . . . . . C1 C 0.56373(6) 0.58363(12) 0.6734(2) 0.0663(4) Uani 1 1 d . . . . . H1 H 0.602017 0.598240 0.635973 0.080 Uiso 1 1 calc R U . . . C2 C 0.49509(6) 0.45687(10) 0.75139(18) 0.0568(3) Uani 1 1 d . . . . . H2 H 0.483577 0.381861 0.770006 0.068 Uiso 1 1 calc R U . . . N2 N 0.52946(5) 0.67290(10) 0.6971(2) 0.0760(4) Uani 1 1 d . . . . . C3 C 0.45420(5) 0.54178(9) 0.78222(16) 0.0477(3) Uani 1 1 d . . . . . C5 C 0.39366(5) 0.52156(10) 0.83940(16) 0.0504(3) Uani 1 1 d . . . . . H5 H 0.367701 0.583574 0.836800 0.060 Uiso 1 1 calc R U . . . C4 C 0.47482(6) 0.65034(11) 0.7514(2) 0.0675(4) Uani 1 1 d . . . . . H4 H 0.449203 0.711224 0.769564 0.081 Uiso 1 1 calc R U . . . C9 C 0.24095(6) 0.28224(11) 1.09473(18) 0.0615(4) Uani 1 1 d . . . . . H9 H 0.233296 0.216239 1.157770 0.074 Uiso 1 1 calc R U . . . C8 C 0.29807(6) 0.30389(10) 1.04241(17) 0.0543(3) Uani 1 1 d . . . . . H8 H 0.328522 0.251794 1.070046 0.065 Uiso 1 1 calc R U . . . C7 C 0.31108(5) 0.40255(9) 0.94873(15) 0.0455(3) Uani 1 1 d . . . . . C6 C 0.37207(5) 0.42310(10) 0.89479(16) 0.0493(3) Uani 1 1 d . . . . . H6 H 0.398242 0.361399 0.899728 0.059 Uiso 1 1 calc R U . . . C12 C 0.26396(5) 0.47782(10) 0.90753(16) 0.0493(3) Uani 1 1 d . . . . . H12 H 0.271203 0.543880 0.844160 0.059 Uiso 1 1 calc R U . . . C11 C 0.20694(6) 0.45558(11) 0.95942(18) 0.0567(3) Uani 1 1 d . . . . . H11 H 0.176076 0.506587 0.930665 0.068 Uiso 1 1 calc R U . . . C10 C 0.19520(6) 0.35791(12) 1.05405(18) 0.0616(4) Uani 1 1 d . . . . . H10 H 0.156695 0.343511 1.089883 0.074 Uiso 1 1 calc R U . . . C17 C 0.10432(5) 0.76465(10) 0.63221(17) 0.0515(3) Uani 1 1 d . . . . . H17 H 0.129028 0.828436 0.631774 0.062 Uiso 1 1 calc R U . . . C24 C 0.20758(6) 0.54828(11) 0.46214(18) 0.0580(3) Uani 1 1 d . . . . . H24 H 0.178784 0.492423 0.437743 0.070 Uiso 1 1 calc R U . . . C23 C 0.26568(7) 0.53060(12) 0.41471(19) 0.0656(4) Uani 1 1 d . . . . . H23 H 0.275573 0.463432 0.357862 0.079 Uiso 1 1 calc R U . . . C22 C 0.30911(6) 0.61178(13) 0.45101(18) 0.0644(4) Uani 1 1 d . . . . . H22 H 0.348199 0.600037 0.418117 0.077 Uiso 1 1 calc R U . . . C21 C 0.29402(6) 0.71099(12) 0.53690(18) 0.0588(3) Uani 1 1 d . . . . . H21 H 0.323250 0.765744 0.563190 0.071 Uiso 1 1 calc R U . . . C20 C 0.23596(5) 0.72921(10) 0.58375(16) 0.0512(3) Uani 1 1 d . . . . . H20 H 0.226459 0.796331 0.641347 0.061 Uiso 1 1 calc R U . . . C19 C 0.19132(5) 0.64870(10) 0.54618(15) 0.0476(3) Uani 1 1 d . . . . . C18 C 0.12908(5) 0.66611(10) 0.59181(16) 0.0509(3) Uani 1 1 d . . . . . H18 H 0.104622 0.601998 0.592515 0.061 Uiso 1 1 calc R U . . . C13 C -0.07006(6) 0.82486(13) 0.7623(2) 0.0714(4) Uani 1.0000(16) 1 d . . P . . H13 H -0.109311 0.839311 0.791351 0.086 Uiso 1.0000(16) 1 calc R U P . . C14 C 0.02020(6) 0.89195(12) 0.6978(2) 0.0709(4) Uani 1.0000(16) 1 d . . P . . H14 H 0.045770 0.953095 0.680905 0.085 Uiso 1.0000(16) 1 calc R U P . . C15 C 0.04237(5) 0.78363(10) 0.67732(16) 0.0495(3) Uani 1.0000(16) 1 d . . P . . C16 C 0.00152(6) 0.69834(11) 0.7051(2) 0.0633(4) Uani 1.0000(16) 1 d . . P . . H16 H 0.014060 0.623274 0.693606 0.076 Uiso 1.0000(16) 1 calc R U P . . N3 N -0.05482(5) 0.71682(10) 0.74743(19) 0.0718(4) Uani 1.0000(16) 1 d . . P . . N4 N -0.03577(6) 0.91435(11) 0.7404(2) 0.0825(4) Uani 1.0000(16) 1 d . . P . . 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 N1 0.0527(6) 0.0557(7) 0.0851(8) -0.0029(6) 0.0144(6) 0.0043(5) C1 0.0536(8) 0.0604(8) 0.0860(10) -0.0088(7) 0.0149(7) -0.0072(6) C2 0.0574(7) 0.0420(6) 0.0716(9) 0.0008(5) 0.0104(6) 0.0017(5) N2 0.0658(8) 0.0482(6) 0.1161(11) -0.0065(6) 0.0260(7) -0.0109(5) C3 0.0498(6) 0.0413(6) 0.0522(7) -0.0024(5) 0.0033(5) -0.0003(5) C5 0.0495(6) 0.0416(6) 0.0604(7) -0.0013(5) 0.0061(5) 0.0048(5) C4 0.0617(8) 0.0409(7) 0.1016(11) -0.0043(7) 0.0204(8) 0.0010(6) C9 0.0710(9) 0.0545(7) 0.0594(8) 0.0084(6) 0.0070(6) -0.0135(6) C8 0.0614(8) 0.0441(6) 0.0574(7) 0.0061(5) 0.0016(6) 0.0000(5) C7 0.0509(6) 0.0412(6) 0.0443(6) -0.0017(5) 0.0023(5) -0.0017(5) C6 0.0501(7) 0.0442(6) 0.0536(7) 0.0020(5) 0.0025(5) 0.0048(5) C12 0.0531(7) 0.0416(6) 0.0534(7) 0.0021(5) 0.0048(5) 0.0000(5) C11 0.0513(7) 0.0557(7) 0.0633(8) -0.0031(6) 0.0039(6) 0.0027(6) C10 0.0554(7) 0.0684(9) 0.0618(8) -0.0016(6) 0.0110(6) -0.0136(6) C17 0.0489(7) 0.0467(6) 0.0593(8) 0.0042(5) 0.0061(5) -0.0009(5) C24 0.0645(8) 0.0498(7) 0.0594(8) -0.0046(6) 0.0007(6) 0.0067(6) C23 0.0743(9) 0.0604(8) 0.0626(8) -0.0070(6) 0.0065(7) 0.0227(7) C22 0.0573(8) 0.0759(9) 0.0611(8) 0.0080(7) 0.0129(6) 0.0205(7) C21 0.0527(7) 0.0600(8) 0.0639(8) 0.0082(6) 0.0060(6) 0.0028(6) C20 0.0533(7) 0.0466(6) 0.0541(7) 0.0005(5) 0.0055(5) 0.0061(5) C19 0.0530(7) 0.0463(6) 0.0434(6) 0.0028(5) 0.0024(5) 0.0067(5) C18 0.0513(7) 0.0485(6) 0.0529(7) -0.0007(5) 0.0019(5) -0.0016(5) C13 0.0462(7) 0.0683(9) 0.1004(12) 0.0075(8) 0.0102(7) 0.0067(6) C14 0.0550(8) 0.0479(7) 0.1109(12) 0.0026(7) 0.0151(8) -0.0001(6) C15 0.0483(7) 0.0475(6) 0.0527(7) 0.0042(5) 0.0023(5) 0.0021(5) C16 0.0565(8) 0.0478(7) 0.0867(10) 0.0059(6) 0.0134(7) 0.0018(6) N3 0.0519(7) 0.0627(7) 0.1020(10) 0.0085(6) 0.0157(6) -0.0022(5) N4 0.0576(7) 0.0558(7) 0.1357(13) 0.0026(7) 0.0207(7) 0.0105(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 _geom_angle_publ_flag C1 N1 C2 115.22(11) . . ? N2 C1 N1 127.18(13) . . ? N2 C1 H1 116.4 . . ? N1 C1 H1 116.4 . . ? N1 C2 C3 124.20(12) . . ? N1 C2 H2 117.9 . . ? C3 C2 H2 117.9 . . ? C1 N2 C4 115.57(12) . . ? C4 C3 C2 114.18(11) . . ? C4 C3 C5 121.52(11) . . ? C2 C3 C5 124.30(11) . . ? C6 C5 C3 126.27(11) . . ? C6 C5 H5 116.9 . . ? C3 C5 H5 116.9 . . ? N2 C4 C3 123.66(12) . . ? N2 C4 H4 118.2 . . ? C3 C4 H4 118.2 . . ? C10 C9 C8 120.26(12) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C8 C7 121.24(12) . . ? C9 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? C8 C7 C12 117.64(11) . . ? C8 C7 C6 119.98(11) . . ? C12 C7 C6 122.37(10) . . ? C5 C6 C7 126.16(11) . . ? C5 C6 H6 116.9 . . ? C7 C6 H6 116.9 . . ? C11 C12 C7 120.90(11) . . ? C11 C12 H12 119.6 . . ? C7 C12 H12 119.6 . . ? C12 C11 C10 120.50(12) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C9 C10 C11 119.46(12) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C18 C17 C15 126.82(11) . . ? C18 C17 H17 116.6 . . ? C15 C17 H17 116.6 . . ? C23 C24 C19 121.05(13) . . ? C23 C24 H24 119.5 . . ? C19 C24 H24 119.5 . . ? C22 C23 C24 120.40(13) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C23 C22 C21 119.34(13) . . ? C23 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? C20 C21 C22 120.43(13) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C21 C20 C19 121.01(12) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C20 C19 C24 117.76(11) . . ? C20 C19 C18 122.38(11) . . ? C24 C19 C18 119.86(11) . . ? C17 C18 C19 126.10(11) . . ? C17 C18 H18 117.0 . . ? C19 C18 H18 117.0 . . ? N4 C13 N3 127.06(13) . . ? N4 C13 H13 116.5 . . ? N3 C13 H13 116.5 . . ? N4 C14 C15 123.83(13) . . ? N4 C14 H14 118.1 . . ? C15 C14 H14 118.1 . . ? C14 C15 C16 114.18(12) . . ? C14 C15 C17 121.22(11) . . ? C16 C15 C17 124.60(11) . . ? N3 C16 C15 124.01(12) . . ? N3 C16 H16 118.0 . . ? C15 C16 H16 118.0 . . ? C13 N3 C16 115.34(12) . . ? C13 N4 C14 115.59(12) . . ? 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 N1 C1 1.3231(18) . ? N1 C2 1.3260(16) . ? C1 N2 1.3151(18) . ? C1 H1 0.9300 . ? C2 C3 1.3796(16) . ? C2 H2 0.9300 . ? N2 C4 1.3338(17) . ? C3 C4 1.3787(17) . ? C3 C5 1.4597(16) . ? C5 C6 1.3283(16) . ? C5 H5 0.9300 . ? C4 H4 0.9300 . ? C9 C10 1.376(2) . ? C9 C8 1.3783(18) . ? C9 H9 0.9300 . ? C8 C7 1.3958(16) . ? C8 H8 0.9300 . ? C7 C12 1.3963(16) . ? C7 C6 1.4616(16) . ? C6 H6 0.9300 . ? C12 C11 1.3762(17) . ? C12 H12 0.9300 . ? C11 C10 1.3836(19) . ? C11 H11 0.9300 . ? C10 H10 0.9300 . ? C17 C18 1.3245(16) . ? C17 C15 1.4587(16) . ? C17 H17 0.9300 . ? C24 C23 1.3791(19) . ? C24 C19 1.3959(17) . ? C24 H24 0.9300 . ? C23 C22 1.377(2) . ? C23 H23 0.9300 . ? C22 C21 1.3834(19) . ? C22 H22 0.9300 . ? C21 C20 1.3779(17) . ? C21 H21 0.9300 . ? C20 C19 1.3919(17) . ? C20 H20 0.9300 . ? C19 C18 1.4632(16) . ? C18 H18 0.9300 . ? C13 N4 1.3153(19) . ? C13 N3 1.3194(18) . ? C13 H13 0.9300 . ? C14 N4 1.3326(17) . ? C14 C15 1.3761(18) . ? C14 H14 0.9300 . ? C15 C16 1.3776(17) . ? C16 N3 1.3316(17) . ? C16 H16 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 C2 N1 C1 N2 -0.4(2) . . . . ? C1 N1 C2 C3 0.3(2) . . . . ? N1 C1 N2 C4 0.3(3) . . . . ? N1 C2 C3 C4 0.0(2) . . . . ? N1 C2 C3 C5 178.95(13) . . . . ? C4 C3 C5 C6 -170.52(14) . . . . ? C2 C3 C5 C6 10.6(2) . . . . ? C1 N2 C4 C3 0.1(2) . . . . ? C2 C3 C4 N2 -0.2(2) . . . . ? C5 C3 C4 N2 -179.17(14) . . . . ? C10 C9 C8 C7 0.4(2) . . . . ? C9 C8 C7 C12 -0.93(18) . . . . ? C9 C8 C7 C6 -179.91(11) . . . . ? C3 C5 C6 C7 -178.73(11) . . . . ? C8 C7 C6 C5 -164.98(12) . . . . ? C12 C7 C6 C5 16.09(19) . . . . ? C8 C7 C12 C11 0.65(18) . . . . ? C6 C7 C12 C11 179.60(11) . . . . ? C7 C12 C11 C10 0.11(19) . . . . ? C8 C9 C10 C11 0.3(2) . . . . ? C12 C11 C10 C9 -0.6(2) . . . . ? C19 C24 C23 C22 0.6(2) . . . . ? C24 C23 C22 C21 0.5(2) . . . . ? C23 C22 C21 C20 -0.8(2) . . . . ? C22 C21 C20 C19 0.1(2) . . . . ? C21 C20 C19 C24 1.00(18) . . . . ? C21 C20 C19 C18 -179.10(11) . . . . ? C23 C24 C19 C20 -1.32(19) . . . . ? C23 C24 C19 C18 178.78(12) . . . . ? C15 C17 C18 C19 179.75(11) . . . . ? C20 C19 C18 C17 17.0(2) . . . . ? C24 C19 C18 C17 -163.11(12) . . . . ? N4 C14 C15 C16 -0.1(2) . . . . ? N4 C14 C15 C17 -179.38(14) . . . . ? C18 C17 C15 C14 -172.74(14) . . . . ? C18 C17 C15 C16 8.1(2) . . . . ? C14 C15 C16 N3 0.3(2) . . . . ? C17 C15 C16 N3 179.52(13) . . . . ? N4 C13 N3 C16 -0.2(3) . . . . ? C15 C16 N3 C13 -0.1(2) . . . . ? N3 C13 N4 C14 0.4(3) . . . . ? C15 C14 N4 C13 -0.2(3) . . . . ?