# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1786 data_disb _manuscript_number B006935N _manuscript_title ; Conformationally stressed phthalocyanines ; _publ_contact_author ;Prof MJ Cook School of Chemical Sciences University of East Anglia Norwich NR4 7TJ UK ; _publ_contact_author_e-mail m.cook@uea.ac.uk _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C72 H98 N8' _chemical_formula_weight 1075.58 _chemical_melting_point ? _chemical_compound_source ? 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' _symmetry_cell_setting C2/c _symmetry_space_group_name_H-M monoclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.433(5) _cell_length_b 33.873(4) _cell_length_c 10.025(4) _cell_angle_alpha 90.00 _cell_angle_beta 110.12(2) _cell_angle_gamma 90.00 _cell_volume 6515.1(31) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour green _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.097 _exptl_crystal_density_method ? _exptl_crystal_F_000 2344 _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'area detector' _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10287 _diffrn_reflns_av_R_equivalents 0.0584 _diffrn_reflns_av_sigmaI/netI 0.0920 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -40 _diffrn_reflns_limit_k_max 40 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 25.51 _reflns_number_total 5349 _reflns_number_observed 2129 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction 'Denzo (Otwinowski and Minor, 1985-97)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 4 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses of fit S are based on F^2^, conventional R- factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.2522P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 'riding model' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0119(36) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5345 _refine_ls_number_parameters 384 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.2028 _refine_ls_R_factor_obs 0.1073 _refine_ls_wR_factor_all 0.3911 _refine_ls_wR_factor_obs 0.2959 _refine_ls_goodness_of_fit_all 0.939 _refine_ls_goodness_of_fit_obs 1.175 _refine_ls_restrained_S_all 0.960 _refine_ls_restrained_S_obs 1.174 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N 0.5000 -0.1813(2) 0.2500 0.088(2) Uani 1 d S . N2 N 0.4372(2) -0.12357(12) 0.2737(4) 0.0847(11) Uani 1 d . . H1 H 0.4696(2) -0.10639(12) 0.2835(4) 0.060(22) Uiso 0.50 calc PR . N3 N 0.3506(2) -0.08150(13) 0.3143(4) 0.0873(11) Uani 1 d . . N4 N 0.4416(2) -0.04056(12) 0.2882(4) 0.0865(11) Uani 1 d . . H2 H 0.4656(2) -0.05805(12) 0.2631(4) 0.066(23) Uiso 0.50 calc PR . N5 N 0.5000 0.0181(2) 0.2500 0.088(2) Uani 1 d S . C1 C 0.4431(3) -0.16262(15) 0.2513(5) 0.0872(13) Uani 1 d . . C2 C 0.3761(3) -0.18147(15) 0.2345(5) 0.0881(14) Uani 1 d . . C3 C 0.3539(3) -0.2210(2) 0.2072(6) 0.102(2) Uani 1 d . . C4 C 0.2846(3) -0.2277(2) 0.1867(6) 0.116(2) Uani 1 d . . H4 H 0.2671(3) -0.2532(2) 0.1665(6) 0.139 Uiso 1 calc R . C5 C 0.2404(3) -0.1977(2) 0.1953(7) 0.124(2) Uani 1 d . . H5 H 0.1938(3) -0.2038(2) 0.1779(7) 0.148 Uiso 1 calc R . C6 C 0.2617(3) -0.1592(2) 0.2283(6) 0.102(2) Uani 1 d . . C7 C 0.3317(3) -0.15172(15) 0.2469(5) 0.0882(14) Uani 1 d . . C8 C 0.3727(2) -0.1154(2) 0.2784(5) 0.0860(13) Uani 1 d . . C9 C 0.3999(3) -0.2545(2) 0.2089(7) 0.116(2) Uani 1 d . . H9A H 0.3796(3) -0.2695(2) 0.1219(7) 0.139 Uiso 1 calc R . H9B H 0.4444(3) -0.2444(2) 0.2097(7) 0.139 Uiso 1 calc R . C10 C 0.4121(8) -0.2813(4) 0.3297(13) 0.284(9) Uani 1 d . . H10A H 0.3878(8) -0.3052(4) 0.2873(13) 0.341 Uiso 1 calc R . H10B H 0.4613(8) -0.2876(4) 0.3575(13) 0.341 Uiso 1 calc R . C11 C 0.4010(7) -0.2784(4) 0.4523(13) 0.208(5) Uani 1 d . . H11 H 0.3632(7) -0.2599(4) 0.4452(13) 0.250 Uiso 1 calc R . C12 C 0.4798(10) -0.2565(6) 0.5232(21) 0.317(8) Uani 1 d . . H12A H 0.4819 -0.2338 0.4674 0.476 Uiso 1 calc . . H12B H 0.5157 -0.2748 0.5237 0.476 Uiso 1 calc . . H12C H 0.4865 -0.2484 0.6188 0.476 Uiso 1 calc . . C13 C 0.3980(11) -0.3092(7) 0.5278(29) 0.446(17) Uani 1 d . . H13A H 0.3896 -0.3009 0.6120 0.669 Uiso 1 calc . . H13B H 0.4414 -0.3233 0.5541 0.669 Uiso 1 calc . . H13C H 0.3609 -0.3262 0.4731 0.669 Uiso 1 calc . . C14 C 0.2112(3) -0.1277(2) 0.2371(8) 0.129(2) Uani 1 d . . H14A H 0.1748(3) -0.1401(2) 0.2640(8) 0.154 Uiso 1 calc R . H14B H 0.2357(3) -0.1095(2) 0.3122(8) 0.154 Uiso 1 calc R . C15 C 0.1778(6) -0.1047(4) 0.1042(16) 0.220(6) Uani 1 d . . H15A H 0.1557(6) -0.0819(4) 0.1291(16) 0.264 Uiso 0.65(3) calc PR 1 H15B H 0.2149(6) -0.0948(4) 0.0735(16) 0.264 Uiso 0.65(3) calc PR 1 H15D H 0.1913(6) -0.1185(4) 0.0327(16) 0.264 Uiso 0.35(3) calc PR 2 H15E H 0.2030(6) -0.0799(4) 0.1202(16) 0.264 Uiso 0.35(3) calc PR 2 C16A C 0.1304(12) -0.1219(7) -0.0089(19) 0.196(10) Uani 0.65(3) d PU 1 H16A H 0.1498(12) -0.1453(7) -0.0391(19) 0.236 Uiso 0.65(3) calc PR 1 C17A C 0.0593(10) -0.1316(8) 0.0107(31) 0.256(14) Uani 0.65(3) d PU 1 H17A H 0.0284 -0.1437 -0.0742 0.385 Uiso 0.65 calc P 1 H17B H 0.0387 -0.1077 0.0290 0.385 Uiso 0.65 calc P 1 H17C H 0.0672 -0.1494 0.0893 0.385 Uiso 0.65 calc P 1 C16B C 0.1024(16) -0.0933(13) 0.0287(36) 0.179(13) Uani 0.35(3) d PU 2 H16D H 0.1065(16) -0.0651(13) 0.0513(36) 0.214 Uiso 0.35(3) calc PR 2 C17B C 0.0530(21) -0.1049(21) 0.1105(56) 0.306(24) Uani 0.35(3) d PU 2 H17D H 0.0063 -0.0969 0.0567 0.459 Uiso 0.35 calc P 2 H17E H 0.0679 -0.0920 0.2013 0.459 Uiso 0.35 calc P 2 H17F H 0.0543 -0.1330 0.1239 0.459 Uiso 0.35 calc P 2 C18 C 0.1048(12) -0.0905(6) -0.1328(17) 0.404(14) Uani 1 d . . H18A H 0.0709 -0.1024 -0.2143 0.606 Uiso 0.65 calc P 1 H18B H 0.1438 -0.0816 -0.1575 0.606 Uiso 0.65 calc P 1 H18C H 0.0843 -0.0684 -0.1019 0.606 Uiso 0.65 calc P 1 H18A H 0.0596 -0.0833 -0.1975 0.606 Uiso 0.35 calc P 2 H18B H 0.1180 -0.1157 -0.1598 0.606 Uiso 0.35 calc P 2 H18C H 0.1383 -0.0709 -0.1357 0.606 Uiso 0.35 calc P 2 C21 C 0.3854(2) -0.0482(2) 0.3273(5) 0.0835(13) Uani 1 d . . C22 C 0.3633(2) -0.01098(15) 0.3766(5) 0.0875(14) Uani 1 d . . C23 C 0.3131(3) -0.0029(2) 0.4363(6) 0.0980(15) Uani 1 d . . C24 C 0.3089(3) 0.0362(2) 0.4716(6) 0.110(2) Uani 1 d . . H24 H 0.2767(3) 0.0429(2) 0.5145(6) 0.132 Uiso 1 calc R . C25 C 0.3505(3) 0.0664(2) 0.4466(6) 0.109(2) Uani 1 d . . H25 H 0.3441(3) 0.0922(2) 0.4714(6) 0.131 Uiso 1 calc R . C26 C 0.4006(3) 0.0589(2) 0.3864(5) 0.0963(15) Uani 1 d . . C27 C 0.4069(2) 0.01859(15) 0.3535(5) 0.0864(13) Uani 1 d . . C28 C 0.4540(2) -0.0011(2) 0.2948(5) 0.0849(13) Uani 1 d . . C29 C 0.2676(3) -0.0332(2) 0.4644(8) 0.130(2) Uani 1 d . . H29A H 0.2530(3) -0.0513(2) 0.3846(8) 0.156 Uiso 1 calc R . H29B H 0.2947(3) -0.0482(2) 0.5475(8) 0.156 Uiso 1 calc R . C30 C 0.2058(4) -0.0182(3) 0.4876(12) 0.198(4) Uani 1 d . . H30A H 0.1830(4) 0.0002(3) 0.4117(12) 0.237 Uiso 1 calc R . H30B H 0.2207(4) -0.0033(3) 0.5757(12) 0.237 Uiso 1 calc R . C31 C 0.1513(6) -0.0486(4) 0.4951(16) 0.235(6) Uani 1 d . . H31 H 0.1271(6) -0.0599(4) 0.4011(16) 0.282 Uiso 1 calc R . C32 C 0.1821(9) -0.0794(6) 0.5972(21) 0.313(9) Uani 1 d . . H32A H 0.2142 -0.0944 0.5666 0.470 Uiso 1 calc . . H32B H 0.1460 -0.0965 0.6047 0.470 Uiso 1 calc . . H32C H 0.2063 -0.0678 0.6882 0.470 Uiso 1 calc . . C33 C 0.1015(8) -0.0258(6) 0.5461(25) 0.349(11) Uani 1 d . . H33A H 0.0804 -0.0052 0.4797 0.523 Uiso 1 calc . . H33B H 0.1262 -0.0145 0.6374 0.523 Uiso 1 calc . . H33C H 0.0659 -0.0433 0.5540 0.523 Uiso 1 calc . . C34 C 0.4454(3) 0.0911(2) 0.3619(6) 0.110(2) Uani 1 d . . H34A H 0.4923(3) 0.0869(2) 0.4282(6) 0.132 Uiso 1 calc R . H34B H 0.4473(3) 0.0873(2) 0.2673(6) 0.132 Uiso 1 calc R . C35 C 0.4275(4) 0.1331(2) 0.3737(8) 0.147(2) Uani 1 d . . H35A H 0.4672(4) 0.1490(2) 0.3749(8) 0.177 Uiso 1 calc R . H35B H 0.4217(4) 0.1366(2) 0.4650(8) 0.177 Uiso 1 calc R . C36 C 0.3645(4) 0.1496(2) 0.2625(7) 0.140(2) Uani 1 d . . H36 H 0.3260(4) 0.1312(2) 0.2517(7) 0.168 Uiso 1 calc R . C37 C 0.3456(7) 0.1879(3) 0.3146(11) 0.237(5) Uani 1 d . . H37A H 0.3427 0.1842 0.4073 0.355 Uiso 1 calc . . H37B H 0.3014 0.1968 0.2503 0.355 Uiso 1 calc . . H37C H 0.3806 0.2073 0.3195 0.355 Uiso 1 calc . . C38 C 0.3687(7) 0.1558(3) 0.1224(9) 0.236(5) Uani 1 d . . H38A H 0.3253 0.1664 0.0603 0.354 Uiso 1 calc . . H38B H 0.3777 0.1310 0.0853 0.354 Uiso 1 calc . . H38C H 0.4057 0.1740 0.1290 0.354 Uiso 1 calc . . 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 0.093(4) 0.087(4) 0.085(3) 0.000 0.032(3) 0.000 N2 0.081(3) 0.082(3) 0.090(3) -0.001(2) 0.027(2) -0.001(2) N3 0.075(2) 0.086(3) 0.095(3) 0.000(2) 0.022(2) 0.000(2) N4 0.076(2) 0.079(3) 0.102(3) -0.001(2) 0.028(2) 0.001(2) N5 0.086(4) 0.080(4) 0.088(4) 0.000 0.019(3) 0.000 C1 0.092(3) 0.083(3) 0.087(3) 0.004(2) 0.030(3) 0.001(3) C2 0.092(3) 0.086(4) 0.085(3) 0.003(2) 0.029(3) -0.008(3) C3 0.110(4) 0.096(4) 0.098(4) -0.004(3) 0.034(3) -0.011(3) C4 0.111(5) 0.102(5) 0.129(5) -0.001(3) 0.034(4) -0.029(4) C5 0.089(4) 0.116(5) 0.153(5) 0.002(4) 0.026(4) -0.023(4) C6 0.090(4) 0.101(4) 0.108(4) 0.011(3) 0.025(3) -0.011(3) C7 0.083(3) 0.089(4) 0.088(3) 0.004(2) 0.024(3) -0.013(3) C8 0.078(3) 0.089(4) 0.084(3) 0.010(2) 0.020(3) 0.001(3) C9 0.135(5) 0.091(4) 0.127(5) -0.007(3) 0.050(4) -0.014(4) C10 0.390(20) 0.302(16) 0.226(12) 0.121(12) 0.190(15) 0.219(15) C11 0.233(12) 0.215(11) 0.217(10) 0.095(8) 0.128(10) 0.072(9) C12 0.309(19) 0.340(21) 0.320(23) -0.020(16) 0.130(16) -0.031(17) C13 0.461(25) 0.381(24) 0.639(37) 0.361(28) 0.372(27) 0.180(21) C14 0.082(4) 0.126(5) 0.170(6) 0.006(4) 0.032(4) -0.002(3) C15 0.155(8) 0.235(12) 0.297(15) 0.144(12) 0.111(10) 0.060(9) C16A 0.190(17) 0.150(15) 0.173(14) 0.001(11) -0.035(12) -0.019(13) C17A 0.134(13) 0.296(27) 0.299(29) 0.025(20) 0.023(15) -0.097(15) C16B 0.171(24) 0.142(24) 0.188(25) 0.033(19) 0.018(19) 0.029(18) C17B 0.205(30) 0.494(66) 0.291(42) -0.125(41) 0.177(32) -0.127(35) C18 0.506(31) 0.381(23) 0.179(13) 0.082(13) -0.072(16) -0.174(20) C21 0.068(3) 0.092(4) 0.083(3) -0.001(2) 0.017(2) 0.002(2) C22 0.072(3) 0.096(4) 0.089(3) -0.006(2) 0.021(3) 0.005(2) C23 0.086(3) 0.104(4) 0.100(4) -0.013(3) 0.027(3) 0.004(3) C24 0.100(4) 0.127(5) 0.102(4) -0.016(3) 0.035(3) 0.017(4) C25 0.106(4) 0.112(4) 0.104(4) -0.019(3) 0.029(3) 0.011(3) C26 0.096(4) 0.093(4) 0.088(3) -0.006(3) 0.015(3) 0.013(3) C27 0.081(3) 0.091(4) 0.079(3) -0.002(2) 0.017(3) 0.010(3) C28 0.078(3) 0.085(3) 0.086(3) -0.005(2) 0.021(3) 0.000(2) C29 0.105(4) 0.151(6) 0.147(5) -0.030(4) 0.061(4) -0.009(4) C30 0.136(7) 0.206(9) 0.282(12) 0.019(8) 0.113(8) -0.006(6) C31 0.148(8) 0.297(16) 0.310(16) 0.046(12) 0.144(10) 0.018(9) C32 0.281(17) 0.331(22) 0.337(22) 0.104(16) 0.119(16) -0.040(15) C33 0.252(15) 0.339(20) 0.552(32) 0.040(18) 0.262(20) -0.007(13) C34 0.122(4) 0.084(4) 0.120(4) -0.015(3) 0.038(4) 0.003(3) C35 0.162(6) 0.127(6) 0.152(6) -0.011(5) 0.053(5) 0.003(5) C36 0.155(6) 0.138(6) 0.113(5) 0.009(4) 0.028(4) 0.054(5) C37 0.326(14) 0.198(10) 0.193(9) -0.036(7) 0.099(10) 0.075(10) C38 0.367(15) 0.223(11) 0.113(6) -0.013(6) 0.077(8) 0.025(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 1.329(5) 2_655 ? N1 C1 1.329(5) . ? N2 C1 1.354(6) . ? N2 C8 1.364(6) . ? N3 C21 1.315(6) . ? N3 C8 1.327(6) . ? N4 C28 1.360(6) . ? N4 C21 1.360(6) . ? N5 C28 1.339(5) . ? N5 C28 1.339(5) 2_655 ? C1 C2 1.466(6) . ? C2 C7 1.391(7) . ? C2 C3 1.409(7) . ? C3 C4 1.378(8) . ? C3 C9 1.471(8) . ? C4 C5 1.381(8) . ? C5 C6 1.380(8) . ? C6 C7 1.400(7) . ? C6 C14 1.507(8) . ? C7 C8 1.462(7) . ? C9 C10 1.463(12) . ? C10 C11 1.328(12) . ? C11 C13 1.302(13) . ? C11 C12 1.69(2) . ? C14 C15 1.490(11) . ? C15 C16A 1.34(2) . ? C15 C16B 1.51(3) . ? C16A C17A 1.57(3) . ? C16A C18 1.58(2) . ? C16B C17B 1.55(5) . ? C16B C18 1.64(4) . ? C21 C22 1.480(7) . ? C22 C23 1.381(7) . ? C22 C27 1.411(7) . ? C23 C24 1.380(7) . ? C23 C29 1.477(8) . ? C24 C25 1.408(8) . ? C25 C26 1.379(7) . ? C26 C27 1.420(7) . ? C26 C34 1.498(8) . ? C27 C28 1.451(6) . ? C29 C30 1.454(9) . ? C30 C31 1.537(13) . ? C31 C32 1.45(2) . ? C31 C33 1.50(2) . ? C34 C35 1.486(8) . ? C35 C36 1.492(9) . ? C36 C38 1.451(10) . ? C36 C37 1.498(10) . ? 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 C1 123.0(6) 2_655 . ? C1 N2 C8 110.2(4) . . ? C21 N3 C8 123.1(4) . . ? C28 N4 C21 109.7(4) . . ? C28 N5 C28 122.1(6) . 2_655 ? N1 C1 N2 126.5(5) . . ? N1 C1 C2 125.2(5) . . ? N2 C1 C2 108.2(4) . . ? C7 C2 C3 121.9(5) . . ? C7 C2 C1 106.7(4) . . ? C3 C2 C1 131.4(5) . . ? C4 C3 C2 115.6(5) . . ? C4 C3 C9 119.5(5) . . ? C2 C3 C9 124.8(5) . . ? C3 C4 C5 122.0(6) . . ? C6 C5 C4 123.4(6) . . ? C5 C6 C7 115.2(5) . . ? C5 C6 C14 121.2(5) . . ? C7 C6 C14 123.5(5) . . ? C2 C7 C6 121.7(5) . . ? C2 C7 C8 106.6(4) . . ? C6 C7 C8 131.7(5) . . ? N3 C8 N2 127.4(4) . . ? N3 C8 C7 124.3(4) . . ? N2 C8 C7 108.1(4) . . ? C10 C9 C3 114.5(6) . . ? C11 C10 C9 133.3(9) . . ? C13 C11 C10 122.5(18) . . ? C13 C11 C12 109.6(16) . . ? C10 C11 C12 88.8(11) . . ? C15 C14 C6 115.5(7) . . ? C16A C15 C14 120.2(14) . . ? C14 C15 C16B 130.9(13) . . ? C15 C16A C17A 114.6(19) . . ? C15 C16A C18 108.6(15) . . ? C17A C16A C18 99.8(19) . . ? C15 C16B C17B 114.0(28) . . ? C15 C16B C18 97.9(24) . . ? C17B C16B C18 141.4(29) . . ? N3 C21 N4 128.0(4) . . ? N3 C21 C22 123.2(4) . . ? N4 C21 C22 108.6(4) . . ? C23 C22 C27 122.4(5) . . ? C23 C22 C21 132.1(5) . . ? C27 C22 C21 105.5(4) . . ? C24 C23 C22 115.0(5) . . ? C24 C23 C29 121.3(5) . . ? C22 C23 C29 123.7(5) . . ? C23 C24 C25 123.8(5) . . ? C26 C25 C24 121.9(6) . . ? C25 C26 C27 114.8(5) . . ? C25 C26 C34 121.7(5) . . ? C27 C26 C34 123.5(5) . . ? C22 C27 C26 122.1(5) . . ? C22 C27 C28 106.6(4) . . ? C26 C27 C28 131.3(5) . . ? N5 C28 N4 127.0(4) . . ? N5 C28 C27 123.6(5) . . ? N4 C28 C27 109.4(4) . . ? C30 C29 C23 115.1(6) . . ? C29 C30 C31 117.1(8) . . ? C32 C31 C33 108.0(14) . . ? C32 C31 C30 111.9(12) . . ? C33 C31 C30 105.1(11) . . ? C35 C34 C26 120.3(5) . . ? C34 C35 C36 118.1(6) . . ? C38 C36 C35 117.0(8) . . ? C38 C36 C37 108.7(7) . . ? C35 C36 C37 108.8(7) . . ? _refine_diff_density_max 0.449 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.052