Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 207 loop_ _publ_author_name 'Fenton Heirtzler' 'Klaus Kulicke' 'Markus Neuburger' _publ_requested_journal 'Perkin Transactions 1' _publ_contact_author_name 'Dr Fenton Heirtzler' _publ_contact_author_address ; School of Physical Sciences University of Kent Chemical Laboratory Canterbury Kent CT2 7NH UNITED KINGDOM ; _publ_contact_author_email 'FRH@UKC.AC.UK' _publ_section_title ; Insights on the Synthesis and Organisational Phenomena of Twisted Pyrazine - Pyridine Hybrids ; data_FH710A _database_code_CSD 170985 _audit_creation_date 97-11-17 _audit_creation_method CRYSTALS #========================================================================== _chemical_name_systematic ; # IUPAC name, in full ? ; _cell_length_a 33.8039(31) _cell_angle_alpha 90 _cell_length_b 7.8999(9) _cell_angle_beta 97.615(7) _cell_length_c 11.7328(9) _cell_angle_gamma 90 _cell_volume 3105.6(5) _symmetry_cell_setting 'monoclinic ' _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,-y,-z' 'x+1/2,y+1/2,z' '-x+1/2,-y+1/2,-z' '-x,y,-z+1/2' 'x,-y,z+1/2' '-x+1/2,y+1/2,-z+1/2' 'x+1/2,-y+1/2,z+1/2' loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0170 0.0090 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International_Tables_Vol_IV_Table_2.2B' 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 'International_Tables_Vol_IV_Table_2.2B' 'N ' 0.0290 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International_Tables_Vol_IV_Table_2.2B' _chemical_formula_sum ' C19 H13 N5 ' _chemical_formula_moiety ' C19 H13 N5 ' _chemical_compound_source ; ? ; _chemical_formula_weight 311.35 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 18 _cell_measurement_theta_max 42 _cell_measurement_temperature 293 _cell_formula_units_Z 8 _exptl_crystal_description ' prism ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_max 0.55 _exptl_crystal_density_diffrn 1.33 _exptl_crystal_density_meas ? _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.63 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '\y scan' _exptl_absorpt_correction_T_min 0.93 _exptl_absorpt_correction_T_max 1.00 _diffrn_standards_interval_time 120 _diffrn_standards_interval_count ? _diffrn_standards_number 3 _diffrn_standards_decay_% 3.59 _diffrn_ambient_temperature 293 _diffrn_reflns_number 3121 _reflns_number_total 2866 _diffrn_reflns_av_R_equivalents 0.02 _reflns_number_observed 2469 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 74.33 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -41 _reflns_limit_h_max 41 _reflns_limit_k_min 0 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _reflns_observed_criterion >3.00\s(I) _refine_diff_density_min -0.12 _refine_diff_density_max 0.20 _refine_ls_number_reflns 2469 _refine_ls_number_parameters 218 _refine_ls_R_factor_obs 0.0382 _refine_ls_wR_factor_obs 0.0419 _refine_ls_goodness_of_fit_obs 1.0995 _refine_ls_shift/esd_max 0.000375 _refine_ls_structure_factor_coef F _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_measurement_method 2\q/\w # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type N1 0.10570(3) -0.0105(1) -0.00782(9) 0.0465 1.0000 Uani C2 0.08905(4) 0.0514(2) 0.0814(1) 0.0412 1.0000 Uani C3 0.10344(4) 0.0132(2) 0.1950(1) 0.0505 1.0000 Uani C4 0.13614(5) -0.0902(2) 0.2174(1) 0.0582 1.0000 Uani C5 0.15354(5) -0.1540(2) 0.1275(1) 0.0604 1.0000 Uani C6 0.13744(4) -0.1107(2) 0.0170(1) 0.0538 1.0000 Uani N7 0.00719(3) 0.3262(2) -0.0694(1) 0.0512 1.0000 Uani C8 0.04444(4) 0.2707(2) -0.0357(1) 0.0416 1.0000 Uani C9 0.05186(4) 0.1524(2) 0.0541(1) 0.0416 1.0000 Uani N10 0.02352(3) 0.1165(2) 0.1205(1) 0.0511 1.0000 Uani C11 -0.01254(4) 0.1829(2) 0.0902(1) 0.0555 1.0000 Uani C12 -0.02114(4) 0.2772(2) -0.0079(1) 0.0556 1.0000 Uani N13 0.11225(3) 0.3599(1) -0.02957(9) 0.0405 1.0000 Uani C14 0.07629(4) 0.3525(2) -0.0922(1) 0.0418 1.0000 Uani C15 0.06819(4) 0.4252(2) -0.2011(1) 0.0532 1.0000 Uani C16 0.09877(5) 0.5078(2) -0.2447(1) 0.0601 1.0000 Uani C17 0.13605(5) 0.5146(2) -0.1813(1) 0.0554 1.0000 Uani C18 0.14190(4) 0.4381(2) -0.0743(1) 0.0437 1.0000 Uani N19 0.20969(4) 0.5372(2) -0.0342(2) 0.0750 1.0000 Uani C20 0.18171(4) 0.4332(2) -0.0034(1) 0.0485 1.0000 Uani C21 0.18923(5) 0.3238(2) 0.0886(1) 0.0604 1.0000 Uani C22 0.22653(5) 0.3215(3) 0.1517(2) 0.0830 1.0000 Uani C23 0.25529(5) 0.4268(3) 0.1207(2) 0.0927 1.0000 Uani C24 0.24580(5) 0.5302(3) 0.0293(2) 0.0935 1.0000 Uani H31 0.0907 0.0584 0.2568 0.0498 1.0000 Uiso H41 0.1467 -0.1176 0.2952 0.0571 1.0000 Uiso H51 0.1764 -0.2270 0.1409 0.0599 1.0000 Uiso H61 0.1498 -0.1554 -0.0457 0.0543 1.0000 Uiso H111 -0.0330 0.1643 0.1383 0.0552 1.0000 Uiso H121 -0.0483 0.3087 -0.0330 0.0541 1.0000 Uiso H151 0.0421 0.4179 -0.2443 0.0518 1.0000 Uiso H161 0.0941 0.5605 -0.3190 0.0587 1.0000 Uiso H171 0.1576 0.5715 -0.2108 0.0561 1.0000 Uiso H211 0.1686 0.2500 0.1084 0.0592 1.0000 Uiso H221 0.2322 0.2472 0.2165 0.0791 1.0000 Uiso H231 0.2816 0.4274 0.1629 0.0847 1.0000 Uiso H241 0.2663 0.6036 0.0083 0.0835 1.0000 Uiso 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 0.0497(6) 0.0506(7) 0.0398(6) -0.0036(5) 0.0083(5) -0.0026(5) C2 0.0424(6) 0.0448(7) 0.0365(6) 0.0001(5) 0.0056(5) -0.0075(5) C3 0.0523(8) 0.0604(9) 0.0391(7) 0.0032(6) 0.0076(6) -0.0021(7) C4 0.0597(9) 0.066(1) 0.0472(8) 0.0125(7) 0.0013(6) 0.0026(7) C5 0.0563(9) 0.0566(9) 0.068(1) 0.0075(8) 0.0057(7) 0.0085(7) C6 0.0549(8) 0.0531(8) 0.0550(8) -0.0063(7) 0.0133(7) 0.0024(7) N7 0.0430(6) 0.0550(7) 0.0546(7) -0.0016(6) 0.0024(5) -0.0011(5) C8 0.0398(6) 0.0473(7) 0.0370(6) -0.0049(5) 0.0022(5) -0.0034(5) C9 0.0393(6) 0.0501(7) 0.0354(6) -0.0053(5) 0.0054(5) -0.0062(5) N10 0.0456(6) 0.0654(8) 0.0436(6) -0.0030(5) 0.0111(5) -0.0082(6) C11 0.0422(7) 0.069(1) 0.0577(8) -0.0092(8) 0.0157(6) -0.0067(7) C12 0.0394(7) 0.0603(9) 0.0667(9) -0.0075(8) 0.0058(6) -0.0013(6) N13 0.0418(5) 0.0436(6) 0.0365(5) -0.0010(4) 0.0071(4) -0.0043(5) C14 0.0442(7) 0.0452(7) 0.0358(6) -0.0015(5) 0.0048(5) -0.0006(5) C15 0.0561(8) 0.0622(9) 0.0398(7) 0.0057(6) 0.0009(6) 0.0047(7) C16 0.077(1) 0.0620(9) 0.0425(7) 0.0129(7) 0.0114(7) 0.0019(8) C17 0.0650(9) 0.0549(8) 0.0496(8) 0.0072(7) 0.0194(7) -0.0076(7) C18 0.0484(7) 0.0402(7) 0.0442(7) -0.0034(6) 0.0128(5) -0.0050(6) N19 0.0498(7) 0.0690(9) 0.108(1) 0.0096(8) 0.0190(7) -0.0119(7) C20 0.0429(7) 0.0483(7) 0.0563(8) -0.0094(6) 0.0142(6) -0.0052(6) C21 0.0520(8) 0.075(1) 0.0532(8) -0.0000(8) 0.0042(6) -0.0063(8) C22 0.060(1) 0.110(2) 0.075(1) 0.005(1) -0.0071(9) 0.001(1) C23 0.048(1) 0.111(2) 0.114(2) -0.010(1) -0.008(1) -0.001(1) C24 0.0443(9) 0.088(1) 0.150(2) -0.000(1) 0.017(1) -0.016(1) _refine_ls_extinction_coef 59.6(47) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C2 . 1.345(2) yes N1 . C6 . 1.334(2) yes C2 . C3 . 1.390(2) yes C2 . C9 . 1.488(2) yes C3 . C4 . 1.372(2) yes C3 . H31 . 0.960(1) no C4 . C5 . 1.370(2) yes C4 . H41 . 0.960(1) no C5 . C6 . 1.380(2) yes C5 . H51 . 0.960(2) no C6 . H61 . 0.960(1) no N7 . C8 . 1.343(2) yes N7 . C12 . 1.330(2) yes C8 . C9 . 1.406(2) yes C8 . C14 . 1.486(2) yes C9 . N10 . 1.342(2) yes N10 . C11 . 1.331(2) yes C11 . C12 . 1.370(2) yes C11 . H111 . 0.960(1) no C12 . H121 . 0.960(1) no N13 . C14 . 1.336(2) yes N13 . C18 . 1.342(2) yes C14 . C15 . 1.394(2) yes C15 . C16 . 1.377(2) yes C15 . H151 . 0.960(1) no C16 . C17 . 1.377(2) yes C16 . H161 . 0.960(1) no C17 . C18 . 1.383(2) yes C17 . H171 . 0.960(1) no C18 . C20 . 1.486(2) yes N19 . C20 . 1.338(2) yes N19 . C24 . 1.344(3) yes C20 . C21 . 1.380(2) yes C21 . C22 . 1.375(2) yes C21 . H211 . 0.960(2) no C22 . C23 . 1.365(3) yes C22 . H221 . 0.960(2) no C23 . C24 . 1.353(3) yes C23 . H231 . 0.960(2) no C24 . H241 . 0.960(2) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . N1 . C6 . 117.0(1) no N1 . C2 . C3 . 122.5(1) no N1 . C2 . C9 . 117.2(1) no C3 . C2 . C9 . 120.1(1) no C2 . C3 . C4 . 119.0(1) no C2 . C3 . H31 . 120.5(1) no C4 . C3 . H31 . 120.5(1) no C3 . C4 . C5 . 119.2(1) no C3 . C4 . H41 . 120.4(2) no C5 . C4 . H41 . 120.4(2) no C4 . C5 . C6 . 118.4(1) no C4 . C5 . H51 . 120.8(2) no C6 . C5 . H51 . 120.8(2) no N1 . C6 . C5 . 123.9(1) no N1 . C6 . H61 . 118.1(1) no C5 . C6 . H61 . 118.1(2) no C8 . N7 . C12 . 117.3(1) no N7 . C8 . C9 . 120.3(1) no N7 . C8 . C14 . 115.7(1) no C9 . C8 . C14 . 123.8(1) no C2 . C9 . C8 . 125.4(1) no C2 . C9 . N10 . 114.2(1) no C8 . C9 . N10 . 120.3(1) no C9 . N10 . C11 . 117.4(1) no N10 . C11 . C12 . 121.5(1) no N10 . C11 . H111 . 119.2(2) no C12 . C11 . H111 . 119.2(1) no N7 . C12 . C11 . 121.8(1) no N7 . C12 . H121 . 119.1(2) no C11 . C12 . H121 . 119.1(1) no C14 . N13 . C18 . 118.5(1) no C8 . C14 . N13 . 115.7(1) no C8 . C14 . C15 . 121.5(1) no N13 . C14 . C15 . 122.7(1) no C14 . C15 . C16 . 118.0(1) no C14 . C15 . H151 . 121.0(1) no C16 . C15 . H151 . 121.0(1) no C15 . C16 . C17 . 119.7(1) no C15 . C16 . H161 . 120.1(2) no C17 . C16 . H161 . 120.1(2) no C16 . C17 . C18 . 118.9(1) no C16 . C17 . H171 . 120.5(1) no C18 . C17 . H171 . 120.5(2) no N13 . C18 . C17 . 122.1(1) no N13 . C18 . C20 . 115.9(1) no C17 . C18 . C20 . 122.0(1) no C20 . N19 . C24 . 116.6(2) no C18 . C20 . N19 . 116.9(1) no C18 . C20 . C21 . 120.9(1) no N19 . C20 . C21 . 122.2(1) no C20 . C21 . C22 . 119.4(2) no C20 . C21 . H211 . 120.3(1) no C22 . C21 . H211 . 120.3(2) no C21 . C22 . C23 . 118.9(2) no C21 . C22 . H221 . 120.6(2) no C23 . C22 . H221 . 120.6(2) no C22 . C23 . C24 . 118.5(2) no C22 . C23 . H231 . 120.8(3) no C24 . C23 . H231 . 120.8(2) no N19 . C24 . C23 . 124.5(2) no N19 . C24 . H241 . 117.7(3) no C23 . C24 . H241 . 117.7(2) no data_FH797A _database_code_CSD 170986 _audit_creation_date 98-12-08 _audit_creation_method CRYSTALS _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435 Carruthers, J.R. and Watkin, D.J. (1979), (Chebychev Weighting) Acta Cryst, A35, 698-699 Davies, K., Braid, P., Foxman, B., Powell, H., SNOOPI, Oxford University, 1989. Enraf Nonius, Delft, NL, CAD4-Express diffractometer control software. North, A. C. T., Phillips, D. C. & Mathews, F. S., absorption correction with \y scans, A24, 351-359 Watkin, D.J., Carruthers, R.J. & Betteridge, P. (1985) CRYSTALS. Chemical Crystallography Laboratory, OXFORD, UK. ; #========================================================================== _chemical_name_systematic ; # IUPAC name, in full ? ; _cell_length_a 7.6365(5) _cell_angle_alpha 90 _cell_length_b 15.3853(12) _cell_angle_beta 94.771(5) _cell_length_c 9.7993(6) _cell_angle_gamma 90 _cell_volume 1147.3(1) _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,-y,-z' '-x,y+1/2,-z+1/2' 'x,-y+1/2,z+1/2' loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International_Tables_Vol_IV_Table_2.2B' 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 'International_Tables_Vol_IV_Table_2.2B' 'N ' 0.0040 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International_Tables_Vol_IV_Table_2.2B' _chemical_formula_sum ' C28 H18 N8 ' _chemical_formula_moiety ' C28 H18 N8 ' _chemical_compound_source 'synthetic' _chemical_formula_weight 466.508 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 18 _cell_measurement_temperature 293 _cell_formula_units_Z 2 _exptl_crystal_description ' nothing special ' _exptl_crystal_colour ' yellow ' _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.35 _exptl_crystal_density_meas ' not measured ' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 0.08 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '\y scan' _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 1.00 _diffrn_standards_interval_time 120 _diffrn_standards_interval_count . _diffrn_standards_number 3 _diffrn_standards_decay_% 2.07 _diffrn_ambient_temperature 293 _diffrn_reflns_number 1866 _reflns_number_total 1750 _diffrn_reflns_av_R_equivalents 0.02 _reflns_number_observed 1077 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 26.32 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min 0 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 12 _reflns_observed_criterion >3.00\s(I) _refine_diff_density_min -0.13 _refine_diff_density_max 0.14 _refine_ls_number_reflns 1077 _refine_ls_number_parameters 164 _refine_ls_R_factor_obs 0.0386 _refine_ls_wR_factor_obs 0.0401 _refine_ls_goodness_of_fit_obs 1.1861 _refine_ls_shift/esd_max 0.000139 _refine_ls_structure_factor_coef F _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_measurement_method 2\q/\w # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type N1 0.0883(3) 0.0128(1) -0.1632(2) 0.0383 1.0000 Uani C1 0.0274(3) 0.0362(2) -0.0439(2) 0.0379 1.0000 Uani C2 0.0162(4) 0.1226(2) -0.0049(3) 0.0458 1.0000 Uani C3 0.0732(4) 0.1864(2) -0.0897(3) 0.0522 1.0000 Uani C4 0.1378(4) 0.1626(2) -0.2121(3) 0.0477 1.0000 Uani C5 0.1437(3) 0.0750(2) -0.2445(2) 0.0389 1.0000 Uani C6 0.2075(3) 0.0452(2) -0.3767(2) 0.0393 1.0000 Uani N2 0.1770(3) 0.0996(1) -0.4824(2) 0.0522 1.0000 Uani C7 0.2153(4) 0.0710(2) -0.6049(3) 0.0555 1.0000 Uani C8 0.2766(4) -0.0119(2) -0.6229(3) 0.0515 1.0000 Uani N3 0.3142(3) -0.0657(1) -0.5192(2) 0.0467 1.0000 Uani C9 0.2849(3) -0.0365(2) -0.3933(2) 0.0393 1.0000 Uani C10 0.3483(3) -0.0952(2) -0.2799(3) 0.0411 1.0000 Uani C11 0.3207(4) -0.1844(2) -0.2899(3) 0.0604 1.0000 Uani C12 0.3875(5) -0.2370(2) -0.1852(4) 0.0780 1.0000 Uani C13 0.4809(5) -0.2004(2) -0.0744(4) 0.0752 1.0000 Uani C14 0.5015(4) -0.1121(2) -0.0710(3) 0.0596 1.0000 Uani N4 0.4386(3) -0.0588(1) -0.1719(2) 0.0469 1.0000 Uani H21 -0.0305 0.1377 0.0800 0.0460 1.0000 Uiso H31 0.0680 0.2465 -0.0642 0.0516 1.0000 Uiso H41 0.1777 0.2058 -0.2731 0.0476 1.0000 Uiso H71 0.1997 0.1092 -0.6824 0.0535 1.0000 Uiso H81 0.2927 -0.0314 -0.7141 0.0499 1.0000 Uiso H111 0.2560 -0.2088 -0.3690 0.0593 1.0000 Uiso H121 0.3689 -0.2987 -0.1895 0.0727 1.0000 Uiso H131 0.5309 -0.2360 -0.0007 0.0751 1.0000 Uiso H141 0.5646 -0.0868 0.0081 0.0583 1.0000 Uiso 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 0.043(1) 0.041(1) 0.032(1) 0.0003(9) 0.0083(9) 0.0025(9) C1 0.036(1) 0.042(2) 0.036(1) -0.002(1) 0.007(1) 0.003(1) C2 0.054(2) 0.044(2) 0.041(1) -0.005(1) 0.014(1) 0.003(1) C3 0.064(2) 0.039(2) 0.054(2) -0.007(1) 0.013(1) 0.004(1) C4 0.056(2) 0.040(2) 0.048(2) 0.005(1) 0.011(1) 0.002(1) C5 0.042(1) 0.040(1) 0.035(1) 0.002(1) 0.005(1) 0.000(1) C6 0.043(1) 0.039(2) 0.036(1) 0.001(1) 0.007(1) -0.005(1) N2 0.067(2) 0.051(1) 0.040(1) 0.011(1) 0.009(1) 0.005(1) C7 0.070(2) 0.062(2) 0.035(1) 0.010(1) 0.008(1) 0.002(2) C8 0.054(2) 0.067(2) 0.034(1) -0.006(1) 0.009(1) -0.004(1) N3 0.053(1) 0.051(1) 0.037(1) -0.004(1) 0.010(1) -0.003(1) C9 0.043(2) 0.042(1) 0.034(1) -0.001(1) 0.010(1) -0.006(1) C10 0.042(2) 0.041(2) 0.042(1) -0.001(1) 0.016(1) 0.001(1) C11 0.080(2) 0.047(2) 0.056(2) -0.000(2) 0.013(2) -0.011(2) C12 0.104(3) 0.040(2) 0.092(3) 0.019(2) 0.020(2) 0.003(2) C13 0.087(3) 0.073(3) 0.067(2) 0.030(2) 0.012(2) 0.014(2) C14 0.059(2) 0.074(2) 0.045(2) 0.008(2) 0.002(1) 0.011(2) N4 0.050(1) 0.052(1) 0.040(1) 0.002(1) 0.007(1) 0.002(1) _refine_ls_extinction_coef 81.4(188) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C1 . 1.343(3) yes N1 . C5 . 1.337(3) yes C1 . C1 2_555 1.488(5) yes C1 . C2 . 1.388(3) yes C2 . C3 . 1.380(4) yes C2 . H21 . 0.960(2) no C3 . C4 . 1.383(4) yes C3 . H31 . 0.960(3) no C4 . C5 . 1.386(3) yes C4 . H41 . 0.960(2) no C5 . C6 . 1.493(3) yes C6 . N2 . 1.337(3) yes C6 . C9 . 1.404(3) yes N2 . C7 . 1.333(3) yes C7 . C8 . 1.374(4) yes C7 . H71 . 0.960(3) no C8 . N3 . 1.324(3) yes C8 . H81 . 0.960(2) no N3 . C9 . 1.349(3) yes C9 . C10 . 1.482(3) yes C10 . C11 . 1.390(4) yes C10 . N4 . 1.338(3) yes C11 . C12 . 1.372(4) yes C11 . H111 . 0.960(3) no C12 . C13 . 1.369(5) yes C12 . H121 . 0.960(3) no C13 . C14 . 1.368(4) yes C13 . H131 . 0.960(3) no C14 . N4 . 1.343(3) yes C14 . H141 . 0.960(3) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . N1 . C5 . 118.5(2) no N1 . C1 . C1 2_555 115.9(3) no N1 . C1 . C2 . 122.0(2) no C1 2_555 C1 . C2 . 122.0(3) no C1 . C2 . C3 . 119.0(2) no C1 . C2 . H21 . 120.5(3) no C3 . C2 . H21 . 120.5(3) no C2 . C3 . C4 . 119.2(2) no C2 . C3 . H31 . 120.4(3) no C4 . C3 . H31 . 120.4(3) no C3 . C4 . C5 . 118.5(2) no C3 . C4 . H41 . 120.8(3) no C5 . C4 . H41 . 120.8(2) no N1 . C5 . C4 . 122.8(2) no N1 . C5 . C6 . 116.1(2) no C4 . C5 . C6 . 121.1(2) no C5 . C6 . N2 . 115.6(2) no C5 . C6 . C9 . 123.1(2) no N2 . C6 . C9 . 121.2(2) no C6 . N2 . C7 . 117.0(2) no N2 . C7 . C8 . 121.7(2) no N2 . C7 . H71 . 119.2(3) no C8 . C7 . H71 . 119.2(3) no C7 . C8 . N3 . 122.4(2) no C7 . C8 . H81 . 118.8(3) no N3 . C8 . H81 . 118.8(3) no C8 . N3 . C9 . 116.9(2) no C6 . C9 . N3 . 120.5(2) no C6 . C9 . C10 . 125.0(2) no N3 . C9 . C10 . 114.5(2) no C9 . C10 . C11 . 120.7(2) no C9 . C10 . N4 . 116.9(2) no C11 . C10 . N4 . 122.3(2) no C10 . C11 . C12 . 119.0(3) no C10 . C11 . H111 . 120.5(3) no C12 . C11 . H111 . 120.5(3) no C11 . C12 . C13 . 119.2(3) no C11 . C12 . H121 . 120.4(4) no C13 . C12 . H121 . 120.4(4) no C12 . C13 . C14 . 118.6(3) no C12 . C13 . H131 . 120.7(4) no C14 . C13 . H131 . 120.7(4) no C13 . C14 . N4 . 123.8(3) no C13 . C14 . H141 . 118.1(3) no N4 . C14 . H141 . 118.1(3) no C10 . N4 . C14 . 117.1(2) no data_fh820a _database_code_CSD 170987 _audit_creation_date 00-01-19 _audit_creation_method CRYSTALS # fh820a #========================================================================== _chemical_name_systematic ; # IUPAC name, in full ? ; _cell_length_a 9.4955(1) _cell_angle_alpha 90 _cell_length_b 27.5691(3) _cell_angle_beta 92.8582(8) _cell_length_c 17.9795(2) _cell_angle_gamma 90 _cell_volume 4700.86 _symmetry_cell_setting 'Monoclinic ' _symmetry_space_group_name_H-M 'P 21/a' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,-y,-z' '-x+1/2,y+1/2,-z' 'x+1/2,-y+1/2,z' loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International_Tables_Vol_IV_Table_2.2B' 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 'International_Tables_Vol_IV_Table_2.2B' 'N ' 0.0040 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International_Tables_Vol_IV_Table_2.2B' _chemical_formula_sum ' 2(C29 H19 N7) ' _chemical_formula_moiety ' 2(C29 H19 N7) ' _chemical_compound_source ; ? ; _chemical_formula_weight 465.52 _cell_measurement_reflns_used 51112 _cell_measurement_theta_min 1 _cell_measurement_theta_max 25 _cell_measurement_temperature 293 _cell_formula_units_Z 8 _exptl_crystal_description ' needle ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.22 _exptl_crystal_density_diffrn 1.32 _exptl_crystal_density_meas ? _exptl_crystal_F_000 1936 _exptl_absorpt_coefficient_mu 0.08 _exptl_absorpt_correction_type none _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 293 _diffrn_reflns_number 51112 _reflns_number_total 16190 _diffrn_reflns_av_R_equivalents 0.00 _reflns_number_observed 10909 _diffrn_reflns_theta_min 1.00 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min -32 _reflns_limit_k_max 32 _reflns_limit_l_min 0 _reflns_limit_l_max 21 _reflns_observed_criterion >2.00\s(I) _refine_diff_density_min -0.58 _refine_diff_density_max 0.53 _refine_ls_number_reflns 10909 _refine_ls_number_parameters 991 _refine_ls_R_factor_obs 0.0522 _refine_ls_wR_factor_obs 0.0805 _refine_ls_goodness_of_fit_obs 0.8836 _refine_ls_shift/esd_max 0.000756 _refine_ls_structure_factor_coef F _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device 'KappaCCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _diffrn_measurement_method 'CCD' # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type N1 -0.2965(1) 0.05193(5) 0.85247(9) 0.0636 1.0000 Uani C1 -0.1747(1) 0.07643(6) 0.85285(9) 0.0483 1.0000 Uani C2 -0.1724(1) 0.12755(5) 0.85814(8) 0.0448 1.0000 Uani N2 -0.2921(1) 0.15310(5) 0.85198(7) 0.0542 1.0000 Uani C3 -0.4120(2) 0.12816(7) 0.8466(1) 0.0612 1.0000 Uani C4 -0.4144(2) 0.07846(8) 0.8510(1) 0.0664 1.0000 Uani N11 0.0437(1) 0.06540(4) 0.79539(7) 0.0485 1.0000 Uani C11 -0.0451(2) 0.04712(5) 0.8431(1) 0.0522 1.0000 Uani C12 -0.0208(2) 0.00389(6) 0.8809(1) 0.0712 1.0000 Uani C13 0.1033(2) -0.02045(6) 0.8692(1) 0.0808 1.0000 Uani C14 0.1965(2) -0.00175(6) 0.8210(1) 0.0693 1.0000 Uani C15 0.1636(2) 0.04124(5) 0.7847(1) 0.0546 1.0000 Uani N12 0.3653(2) 0.03628(6) 0.7087(1) 0.0815 1.0000 Uani C16 0.2606(2) 0.06427(6) 0.73222(9) 0.0578 1.0000 Uani C17 0.2440(2) 0.11210(8) 0.7103(1) 0.0706 1.0000 Uani C18 0.3367(2) 0.1321(1) 0.6620(1) 0.0891 1.0000 Uani C19 0.4429(2) 0.1036(1) 0.6374(1) 0.0907 1.0000 Uani C20 0.4522(2) 0.0568(1) 0.6610(2) 0.0960 1.0000 Uani N21 0.0596(1) 0.13384(4) 0.91571(7) 0.0447 1.0000 Uani C21 -0.0397(1) 0.15537(5) 0.87171(8) 0.0456 1.0000 Uani C22 -0.0210(2) 0.20111(5) 0.8409(1) 0.0569 1.0000 Uani C23 0.1063(2) 0.22402(5) 0.8538(1) 0.0638 1.0000 Uani C24 0.2111(2) 0.20158(5) 0.8969(1) 0.0551 1.0000 Uani C25 0.1838(1) 0.15625(5) 0.92734(8) 0.0448 1.0000 Uani N22 0.4137(1) 0.15223(4) 0.99089(7) 0.0445 1.0000 Uani C26 0.2932(2) 0.12878(5) 0.97278(8) 0.0450 1.0000 Uani C27 0.2719(2) 0.08035(6) 0.9918(1) 0.0571 1.0000 Uani C28 0.3780(2) 0.05590(6) 1.0301(1) 0.0655 1.0000 Uani C29 0.5032(2) 0.07901(6) 1.04789(9) 0.0562 1.0000 Uani C30 0.5182(2) 0.12761(5) 1.02734(8) 0.0450 1.0000 Uani N23 0.7624(2) 0.12722(5) 1.0680(1) 0.0679 1.0000 Uani C31 0.6523(2) 0.15414(5) 1.04362(8) 0.0468 1.0000 Uani C32 0.6645(2) 0.20355(6) 1.0329(1) 0.0563 1.0000 Uani C33 0.7911(2) 0.22609(6) 1.0496(1) 0.0637 1.0000 Uani C34 0.9037(2) 0.19895(7) 1.0753(1) 0.0712 1.0000 Uani C35 0.8842(2) 0.15027(8) 1.0821(1) 0.0828 1.0000 Uani N51 -0.4991(1) -0.13833(5) 0.55306(8) 0.0574 1.0000 Uani C51 -0.3619(2) -0.12719(6) 0.55993(9) 0.0503 1.0000 Uani C52 -0.3183(2) -0.07893(5) 0.57209(9) 0.0499 1.0000 Uani N52 -0.4116(1) -0.04252(5) 0.56757(8) 0.0591 1.0000 Uani C53 -0.5464(2) -0.05420(6) 0.5563(1) 0.0608 1.0000 Uani C54 -0.5904(2) -0.10147(6) 0.5527(1) 0.0584 1.0000 Uani N61 -0.1652(1) -0.16050(4) 0.49956(7) 0.0499 1.0000 Uani C61 -0.2644(2) -0.16855(6) 0.54837(9) 0.0502 1.0000 Uani C62 -0.2835(2) -0.21303(6) 0.5823(1) 0.0576 1.0000 Uani C63 -0.1983(2) -0.25101(6) 0.5645(1) 0.0636 1.0000 Uani C64 -0.0971(2) -0.24397(6) 0.5130(1) 0.0600 1.0000 Uani C65 -0.0827(2) -0.19813(6) 0.48269(9) 0.0526 1.0000 Uani N62 0.0944(2) -0.22601(7) 0.4011(1) 0.0796 1.0000 Uani C66 0.0284(2) -0.18786(7) 0.42921(9) 0.0582 1.0000 Uani C67 0.0624(2) -0.14089(9) 0.4109(1) 0.0834 1.0000 Uani C68 0.1686(3) -0.1323(1) 0.3621(2) 0.1018 1.0000 Uani C69 0.2378(2) -0.1718(1) 0.3353(1) 0.0950 1.0000 Uani C70 0.1984(3) -0.2168(1) 0.3560(1) 0.0945 1.0000 Uani N71 -0.0916(1) -0.09889(4) 0.62954(7) 0.0479 1.0000 Uani C71 -0.1704(2) -0.06475(5) 0.59415(9) 0.0495 1.0000 Uani C72 -0.1207(2) -0.01844(6) 0.5813(1) 0.0651 1.0000 Uani C73 0.0159(2) -0.00711(6) 0.6048(1) 0.0684 1.0000 Uani C74 0.0985(2) -0.04179(6) 0.6402(1) 0.0572 1.0000 Uani C75 0.0410(2) -0.08748(5) 0.65186(8) 0.0469 1.0000 Uani N72 0.2590(1) -0.11507(5) 0.71007(7) 0.0476 1.0000 Uani C76 0.1253(2) -0.12677(5) 0.68992(8) 0.0460 1.0000 Uani C77 0.0699(2) -0.17253(6) 0.70151(9) 0.0539 1.0000 Uani C78 0.1552(2) -0.20718(6) 0.7359(1) 0.0601 1.0000 Uani C79 0.2930(2) -0.19585(6) 0.75625(9) 0.0567 1.0000 Uani C80 0.3423(2) -0.14929(6) 0.74228(8) 0.0482 1.0000 Uani N73 0.5786(2) -0.16924(6) 0.7869(1) 0.0701 1.0000 Uani C81 0.4901(2) -0.13415(6) 0.76162(8) 0.0495 1.0000 Uani C82 0.5331(2) -0.08636(6) 0.75428(9) 0.0571 1.0000 Uani C83 0.6709(2) -0.07368(7) 0.7727(1) 0.0678 1.0000 Uani C84 0.7620(2) -0.10971(9) 0.7977(1) 0.0766 1.0000 Uani C85 0.7117(2) -0.15589(8) 0.8040(1) 0.0821 1.0000 Uani H31 -0.4995 0.1454 0.8395 0.0583 1.0000 Uiso H41 -0.5036 0.0622 0.8531 0.0619 1.0000 Uiso H121 -0.0879 -0.0087 0.9142 0.0658 1.0000 Uiso H131 0.1242 -0.0504 0.8948 0.0708 1.0000 Uiso H141 0.2832 -0.0183 0.8126 0.0643 1.0000 Uiso H171 0.1687 0.1313 0.7285 0.0697 1.0000 Uiso H181 0.3269 0.1652 0.6460 0.0875 1.0000 Uiso H191 0.5095 0.1164 0.6040 0.0850 1.0000 Uiso H201 0.5259 0.0370 0.6423 0.0905 1.0000 Uiso H221 -0.0954 0.2163 0.8112 0.0548 1.0000 Uiso H231 0.1221 0.2555 0.8330 0.0591 1.0000 Uiso H241 0.3012 0.2169 0.9058 0.0533 1.0000 Uiso H271 0.1843 0.0645 0.9784 0.0564 1.0000 Uiso H281 0.3650 0.0227 1.0444 0.0630 1.0000 Uiso H291 0.5791 0.0621 1.0740 0.0558 1.0000 Uiso H321 0.5850 0.2220 1.0138 0.0554 1.0000 Uiso H331 0.8004 0.2605 1.0433 0.0627 1.0000 Uiso H341 0.9933 0.2137 1.0881 0.0697 1.0000 Uiso H351 0.9642 0.1311 1.0983 0.0771 1.0000 Uiso H531 -0.6151 -0.0288 0.5505 0.0590 1.0000 Uiso H541 -0.6896 -0.1083 0.5498 0.0561 1.0000 Uiso H621 -0.3552 -0.2172 0.6176 0.0567 1.0000 Uiso H631 -0.2088 -0.2821 0.5876 0.0622 1.0000 Uiso H641 -0.0381 -0.2702 0.4986 0.0592 1.0000 Uiso H671 0.0130 -0.1142 0.4318 0.0818 1.0000 Uiso H681 0.1926 -0.1000 0.3476 0.1009 1.0000 Uiso H691 0.3133 -0.1676 0.3023 0.0875 1.0000 Uiso H701 0.2487 -0.2440 0.3368 0.0927 1.0000 Uiso H721 -0.1802 0.0053 0.5566 0.0624 1.0000 Uiso H731 0.0529 0.0247 0.5964 0.0645 1.0000 Uiso H741 0.1940 -0.0347 0.6566 0.0554 1.0000 Uiso H771 -0.0259 -0.1799 0.6859 0.0533 1.0000 Uiso H781 0.1189 -0.2389 0.7456 0.0595 1.0000 Uiso H791 0.3541 -0.2197 0.7797 0.0564 1.0000 Uiso H821 0.4670 -0.0622 0.7364 0.0563 1.0000 Uiso H831 0.7024 -0.0408 0.7682 0.0668 1.0000 Uiso H841 0.8591 -0.1025 0.8106 0.0723 1.0000 Uiso H851 0.7765 -0.1805 0.8219 0.0788 1.0000 Uiso 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 0.0472(8) 0.0646(9) 0.078(1) 0.0036(7) -0.0017(7) -0.0136(6) C1 0.0389(8) 0.0504(8) 0.0553(9) 0.0036(6) -0.0023(6) -0.0030(6) C2 0.0389(8) 0.0497(8) 0.0455(8) 0.0003(6) -0.0001(6) 0.0029(6) N2 0.0436(8) 0.0642(8) 0.0547(8) -0.0022(6) 0.0016(6) 0.0105(6) C3 0.0399(9) 0.086(1) 0.0573(9) 0.0005(8) 0.0032(7) 0.0131(8) C4 0.0370(9) 0.094(1) 0.068(1) 0.0000(9) 0.0022(7) -0.0104(8) N11 0.0406(7) 0.0420(6) 0.0622(8) -0.0077(5) -0.0040(6) 0.0033(5) C11 0.0430(8) 0.0397(7) 0.073(1) -0.0020(7) -0.0108(7) -0.0033(6) C12 0.062(1) 0.0426(9) 0.108(1) 0.0165(9) -0.006(1) -0.0075(8) C13 0.075(1) 0.0370(9) 0.128(2) 0.0114(9) -0.020(1) 0.0060(8) C14 0.057(1) 0.0445(9) 0.105(1) -0.0123(9) -0.010(1) 0.0141(8) C15 0.0457(9) 0.0460(8) 0.071(1) -0.0197(7) -0.0093(7) 0.0046(7) N12 0.0494(8) 0.081(1) 0.115(1) -0.044(1) 0.0076(9) 0.0023(8) C16 0.0389(8) 0.068(1) 0.065(1) -0.0241(8) -0.0065(7) 0.0029(7) C17 0.056(1) 0.085(1) 0.070(1) 0.0069(9) 0.0038(9) 0.0134(9) C18 0.078(1) 0.114(2) 0.076(1) 0.021(1) 0.005(1) -0.001(1) C19 0.065(1) 0.140(2) 0.067(1) -0.020(1) 0.008(1) -0.013(1) C20 0.053(1) 0.126(2) 0.110(2) -0.060(2) 0.021(1) -0.009(1) N21 0.0425(7) 0.0424(6) 0.0490(7) -0.0047(5) -0.0014(5) -0.0015(5) C21 0.0432(8) 0.0434(7) 0.0497(8) -0.0056(6) -0.0023(6) 0.0055(6) C22 0.057(1) 0.0402(8) 0.072(1) 0.0028(7) -0.0135(8) 0.0056(7) C23 0.067(1) 0.0355(8) 0.087(1) 0.0074(8) -0.0160(9) -0.0059(7) C24 0.0524(9) 0.0413(8) 0.070(1) -0.0003(7) -0.0114(8) -0.0067(6) C25 0.0443(8) 0.0428(7) 0.0469(8) -0.0061(6) -0.0028(6) 0.0006(6) N22 0.0419(7) 0.0435(6) 0.0473(6) -0.0014(5) -0.0035(5) 0.0000(5) C26 0.0441(8) 0.0459(8) 0.0448(8) 0.0001(6) -0.0001(6) -0.0000(6) C27 0.0527(9) 0.0511(9) 0.067(1) 0.0098(7) -0.0058(7) -0.0090(7) C28 0.064(1) 0.0460(9) 0.085(1) 0.0205(8) -0.0099(9) -0.0098(8) C29 0.0548(9) 0.0533(9) 0.0595(9) 0.0134(7) -0.0072(7) 0.0023(7) C30 0.0465(8) 0.0449(8) 0.0431(7) -0.0002(6) -0.0011(6) 0.0001(6) N23 0.0520(9) 0.0526(8) 0.097(1) 0.0123(7) -0.0176(7) 0.0015(6) C31 0.0462(8) 0.0488(8) 0.0448(7) 0.0011(6) -0.0035(6) 0.0034(6) C32 0.0524(9) 0.0489(8) 0.066(1) 0.0055(7) -0.0096(7) 0.0005(7) C33 0.064(1) 0.0520(9) 0.074(1) 0.0094(8) -0.0093(8) -0.0111(8) C34 0.057(1) 0.071(1) 0.084(1) 0.0128(9) -0.0155(9) -0.0168(9) C35 0.052(1) 0.074(1) 0.120(2) 0.024(1) -0.026(1) 0.0016(9) N51 0.0435(7) 0.0629(8) 0.0653(8) -0.0017(6) -0.0010(6) -0.0016(6) C51 0.0443(8) 0.0549(9) 0.0512(8) 0.0050(6) -0.0032(6) 0.0019(7) C52 0.0453(8) 0.0517(8) 0.0524(9) 0.0045(6) -0.0003(6) 0.0039(7) N52 0.0501(8) 0.0554(8) 0.0712(9) 0.0039(6) -0.0044(6) 0.0102(6) C53 0.0422(9) 0.068(1) 0.071(1) 0.0067(8) -0.0026(7) 0.0140(8) C54 0.0376(8) 0.075(1) 0.063(1) 0.0022(8) 0.0018(7) 0.0031(7) N61 0.0425(7) 0.0518(7) 0.0549(7) 0.0020(5) -0.0038(6) 0.0017(6) C61 0.0401(8) 0.0519(8) 0.0573(9) -0.0018(6) -0.0092(7) 0.0012(6) C62 0.0478(9) 0.0545(9) 0.070(1) 0.0080(8) -0.0002(7) -0.0040(7) C63 0.063(1) 0.0485(9) 0.079(1) 0.0111(8) -0.0026(9) 0.0019(7) C64 0.057(1) 0.0511(9) 0.072(1) 0.0022(7) -0.0047(8) 0.0100(7) C65 0.0427(9) 0.0595(9) 0.0544(9) 0.0005(7) -0.0090(7) 0.0052(7) N62 0.078(1) 0.088(1) 0.074(1) -0.0040(8) 0.0167(9) 0.0167(9) C66 0.0462(9) 0.072(1) 0.0556(9) 0.0074(8) -0.0070(7) 0.0070(8) C67 0.061(1) 0.088(1) 0.103(2) 0.014(1) 0.017(1) 0.004(1) C68 0.080(2) 0.111(2) 0.116(2) 0.031(2) 0.019(1) -0.008(1) C69 0.067(1) 0.154(3) 0.065(1) 0.008(1) 0.013(1) -0.002(1) C70 0.089(2) 0.124(2) 0.072(1) -0.004(1) 0.020(1) 0.014(1) N71 0.0422(7) 0.0490(7) 0.0520(7) -0.0007(5) -0.0034(5) 0.0024(5) C71 0.0447(8) 0.0467(8) 0.0563(8) -0.0012(6) -0.0040(6) 0.0029(6) C72 0.059(1) 0.0478(9) 0.087(1) 0.0070(8) -0.0176(9) 0.0027(7) C73 0.061(1) 0.0456(9) 0.097(1) 0.0092(8) -0.0173(9) -0.0071(8) C74 0.0455(9) 0.0498(9) 0.075(1) -0.0029(7) -0.0090(7) -0.0044(7) C75 0.0432(8) 0.0488(8) 0.0484(8) -0.0043(6) -0.0015(6) 0.0028(6) N72 0.0401(7) 0.0518(7) 0.0502(7) -0.0028(5) -0.0028(5) 0.0028(5) C76 0.0439(8) 0.0509(8) 0.0428(8) -0.0040(6) -0.0013(6) 0.0034(6) C77 0.0457(8) 0.0545(9) 0.0609(9) 0.0016(7) -0.0020(7) -0.0026(7) C78 0.060(1) 0.0501(9) 0.070(1) 0.0069(7) 0.0005(8) -0.0042(7) C79 0.056(1) 0.0523(9) 0.0609(9) 0.0055(7) -0.0015(8) 0.0078(7) C80 0.0477(8) 0.0539(8) 0.0428(8) -0.0034(6) -0.0011(6) 0.0072(7) N73 0.0534(9) 0.0666(9) 0.089(1) 0.0003(8) -0.0126(7) 0.0115(7) C81 0.0432(8) 0.0590(9) 0.0458(8) -0.0049(6) -0.0039(6) 0.0096(7) C82 0.0471(9) 0.063(1) 0.060(1) -0.0034(7) -0.0071(7) 0.0064(8) C83 0.055(1) 0.072(1) 0.075(1) -0.0086(9) -0.0060(9) -0.0062(8) C84 0.046(1) 0.098(2) 0.085(1) -0.007(1) -0.0124(9) 0.0022(9) C85 0.056(1) 0.087(1) 0.101(2) 0.002(1) -0.021(1) 0.018(1) _refine_ls_extinction_coef 433.7(1668) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C1 . 1.339(2) yes N1 . C4 . 1.336(2) yes C1 . C2 . 1.413(2) yes C1 . C11 . 1.490(2) yes C2 . N2 . 1.337(2) yes C2 . C21 . 1.485(2) yes N2 . C3 . 1.329(2) yes C3 . C4 . 1.373(3) yes C3 . H31 . 0.960(2) no C4 . H41 . 0.960(2) no N11 . C11 . 1.332(2) yes N11 . C15 . 1.342(2) yes C11 . C12 . 1.386(2) yes C12 . C13 . 1.381(3) yes C12 . H121 . 0.960(2) no C13 . C14 . 1.370(3) yes C13 . H131 . 0.960(2) no C14 . C15 . 1.381(3) yes C14 . H141 . 0.960(2) no C15 . C16 . 1.493(3) yes N12 . C16 . 1.343(2) yes N12 . C20 . 1.344(3) yes C16 . C17 . 1.383(3) yes C17 . C18 . 1.382(3) yes C17 . H171 . 0.960(2) no C18 . C19 . 1.369(3) yes C18 . H181 . 0.960(2) no C19 . C20 . 1.359(4) yes C19 . H191 . 0.960(2) no C20 . H201 . 0.960(2) no N21 . C21 . 1.339(2) yes N21 . C25 . 1.339(2) yes C21 . C22 . 1.393(2) yes C22 . C23 . 1.373(2) yes C22 . H221 . 0.960(2) no C23 . C24 . 1.377(2) yes C23 . H231 . 0.960(2) no C24 . C25 . 1.394(2) yes C24 . H241 . 0.960(2) no C25 . C26 . 1.495(2) yes N22 . C26 . 1.340(2) yes N22 . C30 . 1.346(2) yes C26 . C27 . 1.396(2) yes C27 . C28 . 1.369(2) yes C27 . H271 . 0.960(2) no C28 . C29 . 1.373(2) yes C28 . H281 . 0.960(2) no C29 . C30 . 1.399(2) yes C29 . H291 . 0.960(2) no C30 . C31 . 1.485(2) yes N23 . C31 . 1.338(2) yes N23 . C35 . 1.333(2) yes C31 . C32 . 1.381(2) yes C32 . C33 . 1.373(2) yes C32 . H321 . 0.960(2) no C33 . C34 . 1.367(3) yes C33 . H331 . 0.960(2) no C34 . C35 . 1.361(3) yes C34 . H341 . 0.960(2) no C35 . H351 . 0.960(2) no N51 . C51 . 1.339(2) yes N51 . C54 . 1.335(2) yes C51 . C52 . 1.407(2) yes C51 . C61 . 1.489(2) yes C52 . N52 . 1.339(2) yes C52 . C71 . 1.492(2) yes N52 . C53 . 1.325(2) yes C53 . C54 . 1.369(3) yes C53 . H531 . 0.960(2) no C54 . H541 . 0.960(2) no N61 . C61 . 1.338(2) yes N61 . C65 . 1.344(2) yes C61 . C62 . 1.385(2) yes C62 . C63 . 1.371(2) yes C62 . H621 . 0.960(2) no C63 . C64 . 1.380(3) yes C63 . H631 . 0.960(2) no C64 . C65 . 1.386(2) yes C64 . H641 . 0.960(2) no C65 . C66 . 1.489(2) yes N62 . C66 . 1.337(2) yes N62 . C70 . 1.333(3) yes C66 . C67 . 1.379(3) yes C67 . C68 . 1.389(3) yes C67 . H671 . 0.960(2) no C68 . C69 . 1.372(4) yes C68 . H681 . 0.960(3) no C69 . C70 . 1.353(4) yes C69 . H691 . 0.960(2) no C70 . H701 . 0.960(3) no N71 . C71 . 1.343(2) yes N71 . C75 . 1.340(2) yes C71 . C72 . 1.384(2) yes C72 . C73 . 1.379(3) yes C72 . H721 . 0.960(2) no C73 . C74 . 1.373(2) yes C73 . H731 . 0.960(2) no C74 . C75 . 1.393(2) yes C74 . H741 . 0.960(2) no C75 . C76 . 1.493(2) yes N72 . C76 . 1.342(2) yes N72 . C80 . 1.344(2) yes C76 . C77 . 1.387(2) yes C77 . C78 . 1.379(2) yes C77 . H771 . 0.960(2) no C78 . C79 . 1.376(3) yes C78 . H781 . 0.960(2) no C79 . C80 . 1.393(2) yes C79 . H791 . 0.960(2) no C80 . C81 . 1.488(2) yes N73 . C81 . 1.346(2) yes N73 . C85 . 1.338(3) yes C81 . C82 . 1.388(2) yes C82 . C83 . 1.378(2) yes C82 . H821 . 0.960(2) no C83 . C84 . 1.378(3) yes C83 . H831 . 0.960(2) no C84 . C85 . 1.366(3) yes C84 . H841 . 0.960(2) no C85 . H851 . 0.960(2) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . N1 . C4 . 116.5(1) no N1 . C1 . C2 . 120.9(1) no N1 . C1 . C11 . 116.4(1) no C2 . C1 . C11 . 122.6(1) no C1 . C2 . N2 . 120.7(1) no C1 . C2 . C21 . 122.5(1) no N2 . C2 . C21 . 116.9(1) no C2 . N2 . C3 . 117.1(1) no N2 . C3 . C4 . 121.9(1) no N2 . C3 . H31 . 119.0(2) no C4 . C3 . H31 . 119.0(2) no N1 . C4 . C3 . 122.1(1) no N1 . C4 . H41 . 118.9(2) no C3 . C4 . H41 . 118.9(2) no C11 . N11 . C15 . 118.3(1) no C1 . C11 . N11 . 115.1(1) no C1 . C11 . C12 . 121.8(2) no N11 . C11 . C12 . 123.1(2) no C11 . C12 . C13 . 117.7(2) no C11 . C12 . H121 . 121.1(2) no C13 . C12 . H121 . 121.1(2) no C12 . C13 . C14 . 119.8(2) no C12 . C13 . H131 . 120.1(2) no C14 . C13 . H131 . 120.1(2) no C13 . C14 . C15 . 119.0(2) no C13 . C14 . H141 . 120.5(2) no C15 . C14 . H141 . 120.5(2) no N11 . C15 . C14 . 122.1(2) no N11 . C15 . C16 . 115.7(1) no C14 . C15 . C16 . 122.1(2) no C16 . N12 . C20 . 116.6(2) no C15 . C16 . N12 . 116.4(2) no C15 . C16 . C17 . 121.4(1) no N12 . C16 . C17 . 122.2(2) no C16 . C17 . C18 . 119.4(2) no C16 . C17 . H171 . 120.3(2) no C18 . C17 . H171 . 120.3(2) no C17 . C18 . C19 . 118.5(2) no C17 . C18 . H181 . 120.7(2) no C19 . C18 . H181 . 120.7(2) no C18 . C19 . C20 . 118.8(2) no C18 . C19 . H191 . 120.6(3) no C20 . C19 . H191 . 120.6(3) no N12 . C20 . C19 . 124.4(2) no N12 . C20 . H201 . 117.8(3) no C19 . C20 . H201 . 117.8(3) no C21 . N21 . C25 . 118.5(1) no C2 . C21 . N21 . 115.8(1) no C2 . C21 . C22 . 121.8(1) no N21 . C21 . C22 . 122.4(1) no C21 . C22 . C23 . 118.5(1) no C21 . C22 . H221 . 120.7(2) no C23 . C22 . H221 . 120.7(1) no C22 . C23 . C24 . 119.6(1) no C22 . C23 . H231 . 120.2(2) no C24 . C23 . H231 . 120.2(2) no C23 . C24 . C25 . 118.7(1) no C23 . C24 . H241 . 120.6(2) no C25 . C24 . H241 . 120.6(2) no N21 . C25 . C24 . 122.1(1) no N21 . C25 . C26 . 115.7(1) no C24 . C25 . C26 . 122.1(1) no C26 . N22 . C30 . 118.4(1) no C25 . C26 . N22 . 116.7(1) no C25 . C26 . C27 . 120.9(1) no N22 . C26 . C27 . 122.3(1) no C26 . C27 . C28 . 118.8(1) no C26 . C27 . H271 . 120.6(2) no C28 . C27 . H271 . 120.6(2) no C27 . C28 . C29 . 119.8(1) no C27 . C28 . H281 . 120.1(2) no C29 . C28 . H281 . 120.1(2) no C28 . C29 . C30 . 118.8(1) no C28 . C29 . H291 . 120.6(2) no C30 . C29 . H291 . 120.6(2) no N22 . C30 . C29 . 122.0(1) no N22 . C30 . C31 . 116.9(1) no C29 . C30 . C31 . 121.2(1) no C31 . N23 . C35 . 117.0(1) no C30 . C31 . N23 . 116.1(1) no C30 . C31 . C32 . 122.4(1) no N23 . C31 . C32 . 121.5(1) no C31 . C32 . C33 . 119.6(1) no C31 . C32 . H321 . 120.2(2) no C33 . C32 . H321 . 120.2(2) no C32 . C33 . C34 . 119.2(2) no C32 . C33 . H331 . 120.4(2) no C34 . C33 . H331 . 120.4(2) no C33 . C34 . C35 . 117.5(2) no C33 . C34 . H341 . 121.2(2) no C35 . C34 . H341 . 121.2(2) no N23 . C35 . C34 . 125.0(2) no N23 . C35 . H351 . 117.5(2) no C34 . C35 . H351 . 117.5(2) no C51 . N51 . C54 . 117.0(1) no N51 . C51 . C52 . 120.6(1) no N51 . C51 . C61 . 114.8(1) no C52 . C51 . C61 . 124.4(1) no C51 . C52 . N52 . 120.7(1) no C51 . C52 . C71 . 123.7(1) no N52 . C52 . C71 . 115.6(1) no C52 . N52 . C53 . 117.3(1) no N52 . C53 . C54 . 121.9(1) no N52 . C53 . H531 . 119.0(2) no C54 . C53 . H531 . 119.0(2) no N51 . C54 . C53 . 121.9(1) no N51 . C54 . H541 . 119.1(2) no C53 . C54 . H541 . 119.1(2) no C61 . N61 . C65 . 117.2(1) no C51 . C61 . N61 . 115.3(1) no C51 . C61 . C62 . 121.4(1) no N61 . C61 . C62 . 123.2(1) no C61 . C62 . C63 . 118.8(2) no C61 . C62 . H621 . 120.6(2) no C63 . C62 . H621 . 120.6(2) no C62 . C63 . C64 . 119.2(1) no C62 . C63 . H631 . 120.4(2) no C64 . C63 . H631 . 120.4(2) no C63 . C64 . C65 . 118.6(1) no C63 . C64 . H641 . 120.7(2) no C65 . C64 . H641 . 120.7(2) no N61 . C65 . C64 . 123.0(2) no N61 . C65 . C66 . 116.0(1) no C64 . C65 . C66 . 121.0(1) no C66 . N62 . C70 . 117.2(2) no C65 . C66 . N62 . 117.1(2) no C65 . C66 . C67 . 121.0(2) no N62 . C66 . C67 . 121.9(2) no C66 . C67 . C68 . 119.8(2) no C66 . C67 . H671 . 120.1(2) no C68 . C67 . H671 . 120.1(2) no C67 . C68 . C69 . 117.6(2) no C67 . C68 . H681 . 121.2(3) no C69 . C68 . H681 . 121.2(3) no C68 . C69 . C70 . 119.2(2) no C68 . C69 . H691 . 120.4(3) no C70 . C69 . H691 . 120.4(3) no N62 . C70 . C69 . 124.4(2) no N62 . C70 . H701 . 117.8(3) no C69 . C70 . H701 . 117.8(2) no C71 . N71 . C75 . 118.1(1) no C52 . C71 . N71 . 115.9(1) no C52 . C71 . C72 . 121.4(1) no N71 . C71 . C72 . 122.6(1) no C71 . C72 . C73 . 118.8(1) no C71 . C72 . H721 . 120.6(2) no C73 . C72 . H721 . 120.6(2) no C72 . C73 . C74 . 119.4(1) no C72 . C73 . H731 . 120.3(2) no C74 . C73 . H731 . 120.3(2) no C73 . C74 . C75 . 118.7(1) no C73 . C74 . H741 . 120.6(2) no C75 . C74 . H741 . 120.6(2) no N71 . C75 . C74 . 122.5(1) no N71 . C75 . C76 . 116.2(1) no C74 . C75 . C76 . 121.3(1) no C76 . N72 . C80 . 118.4(1) no C75 . C76 . N72 . 115.3(1) no C75 . C76 . C77 . 122.0(1) no N72 . C76 . C77 . 122.6(1) no C76 . C77 . C78 . 118.6(1) no C76 . C77 . H771 . 120.7(2) no C78 . C77 . H771 . 120.7(2) no C77 . C78 . C79 . 119.4(1) no C77 . C78 . H781 . 120.3(2) no C79 . C78 . H781 . 120.3(2) no C78 . C79 . C80 . 119.0(1) no C78 . C79 . H791 . 120.5(2) no C80 . C79 . H791 . 120.5(2) no N72 . C80 . C79 . 121.9(1) no N72 . C80 . C81 . 115.6(1) no C79 . C80 . C81 . 122.5(1) no C81 . N73 . C85 . 116.6(2) no C80 . C81 . N73 . 116.3(1) no C80 . C81 . C82 . 121.5(1) no N73 . C81 . C82 . 122.2(1) no C81 . C82 . C83 . 119.9(2) no C81 . C82 . H821 . 120.1(2) no C83 . C82 . H821 . 120.1(2) no C82 . C83 . C84 . 117.9(2) no C82 . C83 . H831 . 121.0(2) no C84 . C83 . H831 . 121.0(2) no C83 . C84 . C85 . 118.8(2) no C83 . C84 . H841 . 120.6(2) no C85 . C84 . H841 . 120.6(2) no N73 . C85 . C84 . 124.6(2) no N73 . C85 . H851 . 117.7(2) no C84 . C85 . H851 . 117.7(2) no