#------------------------------------------------------------------------------ #$Date: 2014-07-07 11:39:25 +0300 (Mon, 07 Jul 2014) $ #$Revision: 119492 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/21/66/7216643.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_7216643 loop_ _publ_author_name 'Yasmin, Lyzu' 'Eggers, Paul K.' 'Skelton, Brian W.' 'Stubbs, Keith A.' 'Raston, Colin L.' _publ_section_title ; Thin film microfluidic synthesis of fluorescent highly substituted pyridines ; _journal_issue 7 _journal_name_full 'Green Chemistry' _journal_page_first 3450 _journal_paper_doi 10.1039/c4gc00881b _journal_volume 16 _journal_year 2014 _chemical_formula_moiety 'C27 H26 N2' _chemical_formula_sum 'C27 H26 N2' _chemical_formula_weight 378.5 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2013-10-10T21:17:50-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 99.776(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.4217(3) _cell_length_b 23.8402(8) _cell_length_c 11.7942(4) _cell_measurement_reflns_used 3895 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.993 _cell_measurement_theta_min 2.907 _cell_volume 2056.50(13) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_molecular_graphics 'OrtepII (Johnson, C. K. (1976)' _computing_publication_material 'WinGX Farrugia, L. J. (1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 16.0009 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur diffractometer' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0690379 _diffrn_orient_matrix_UB_12 0.0193523 _diffrn_orient_matrix_UB_13 -0.0086095 _diffrn_orient_matrix_UB_21 0.0338878 _diffrn_orient_matrix_UB_22 -0.0195151 _diffrn_orient_matrix_UB_23 -0.0366302 _diffrn_orient_matrix_UB_31 -0.0590977 _diffrn_orient_matrix_UB_32 0.011423 _diffrn_orient_matrix_UB_33 -0.0479997 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_av_unetI/netI 0.0325 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 13457 _diffrn_reflns_theta_full 26 _diffrn_reflns_theta_max 26 _diffrn_reflns_theta_min 2.78 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.76426 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_method 'not measured' _exptl_crystal_description slab _exptl_crystal_F_000 808 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.383 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.052 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.143 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 266 _refine_ls_number_reflns 4047 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.143 _refine_ls_R_factor_all 0.1015 _refine_ls_R_factor_gt 0.0824 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0739P)^2^+1.5065P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1897 _refine_ls_wR_factor_ref 0.2007 _reflns_number_gt 3289 _reflns_number_total 4047 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL ly02 in P21/c CELL 0.71073 7.4217 23.8402 11.7942 90.000 99.776 90.000 ZERR 4.00 0.0003 0.0008 0.0004 0.000 0.004 0.000 LATT 1 SYMM X, 1/2 - Y, 1/2 + Z SFAC C H N UNIT 108 104 8 MERG 2 OMIT 0.00 52.00 FMAP 2 PLAN 25 ACTA BOND $H WGHT 0.07310 1.49340 L.S. 4 TEMP -173.00 FVAR 1.97761 N11 3 0.513711 0.375292 0.288457 11.00000 0.02833 0.02867 = 0.03088 -0.00030 0.00457 -0.00169 C12 1 0.416225 0.373839 0.182198 11.00000 0.02516 0.02900 = 0.03040 -0.00036 0.00969 0.00079 C13 1 0.361520 0.421870 0.119327 11.00000 0.02992 0.03082 = 0.02863 -0.00037 0.00574 -0.00006 AFIX 43 H13 2 0.294690 0.418731 0.043410 11.00000 -1.20000 AFIX 0 C14 1 0.404297 0.474969 0.167189 11.00000 0.02720 0.02902 = 0.03026 -0.00014 0.00939 0.00185 C15 1 0.502733 0.475840 0.277959 11.00000 0.04046 0.02486 = 0.03457 -0.00319 0.00438 -0.00366 AFIX 43 H15 2 0.532987 0.510765 0.315135 11.00000 -1.20000 AFIX 0 C16 1 0.558027 0.426015 0.335634 11.00000 0.03072 0.02890 = 0.03174 -0.00039 0.00759 -0.00310 C121 1 0.367637 0.316370 0.133646 11.00000 0.02453 0.02789 = 0.03203 0.00049 0.00801 0.00170 C122 1 0.405493 0.268829 0.202217 11.00000 0.04032 0.03256 = 0.03072 -0.00184 0.00158 0.00041 AFIX 43 H122 2 0.465420 0.272795 0.279632 11.00000 -1.20000 AFIX 0 C123 1 0.356993 0.215755 0.159159 11.00000 0.04231 0.02860 = 0.03804 0.00398 0.00641 0.00177 AFIX 43 H123 2 0.383529 0.184156 0.208229 11.00000 -1.20000 AFIX 0 C124 1 0.271500 0.207613 0.047324 11.00000 0.03168 0.03186 = 0.03870 -0.00368 0.00901 -0.00195 C125 1 0.235445 0.254693 -0.021566 11.00000 0.03279 0.03405 = 0.03254 -0.00349 0.00065 -0.00158 AFIX 43 H125 2 0.177878 0.250424 -0.099404 11.00000 -1.20000 AFIX 0 C126 1 0.282072 0.308277 0.021189 11.00000 0.03542 0.02972 = 0.03407 0.00089 0.00216 -0.00050 AFIX 43 H126 2 0.254514 0.339827 -0.027897 11.00000 -1.20000 AFIX 0 C127 1 0.218491 0.149796 -0.000245 11.00000 0.04461 0.03529 = 0.04721 -0.00516 0.00829 -0.00468 AFIX 137 H12A 2 0.268510 0.121325 0.056384 11.00000 -1.50000 H12B 2 0.267729 0.144041 -0.071382 11.00000 -1.50000 H12C 2 0.084940 0.146616 -0.016512 11.00000 -1.50000 AFIX 0 C141 1 0.347541 0.526955 0.102046 11.00000 0.02946 0.02718 = 0.03013 -0.00163 0.00746 0.00153 C142 1 0.231957 0.526340 -0.003185 11.00000 0.04736 0.02576 = 0.03740 -0.00322 0.00481 -0.00168 AFIX 43 H142 2 0.189347 0.491167 -0.034845 11.00000 -1.20000 AFIX 0 C143 1 0.175824 0.574226 -0.064125 11.00000 0.04057 0.03485 = 0.03361 -0.00031 0.00072 0.00095 AFIX 43 H143 2 0.098874 0.571219 -0.136954 11.00000 -1.20000 AFIX 0 C144 1 0.230465 0.627498 -0.020390 11.00000 0.02937 0.03179 = 0.04063 0.00271 0.00921 0.00406 C145 1 0.348627 0.628544 0.085441 11.00000 0.03857 0.02389 = 0.04646 -0.00227 0.00430 -0.00075 AFIX 43 H145 2 0.391114 0.663656 0.117486 11.00000 -1.20000 AFIX 0 C146 1 0.405131 0.580037 0.144526 11.00000 0.03403 0.02957 = 0.03687 0.00118 -0.00022 -0.00078 AFIX 43 H146 2 0.485497 0.582676 0.216167 11.00000 -1.20000 AFIX 0 N144 3 0.170371 0.675656 -0.078125 11.00000 0.04445 0.02994 = 0.05109 0.00596 -0.00189 0.00410 C147 1 0.083890 0.673952 -0.196910 11.00000 0.03893 0.03973 = 0.05371 0.01339 0.00547 0.00636 AFIX 137 H14A 2 0.165787 0.655788 -0.242720 11.00000 -1.50000 H14B 2 0.057377 0.712264 -0.224978 11.00000 -1.50000 H14C 2 -0.030389 0.652645 -0.203923 11.00000 -1.50000 AFIX 0 C148 1 0.219155 0.729904 -0.025995 11.00000 0.04268 0.02828 = 0.07181 0.00784 0.01021 0.00577 AFIX 137 H14D 2 0.201143 0.729377 0.054411 11.00000 -1.50000 H14E 2 0.141602 0.758981 -0.067999 11.00000 -1.50000 H14F 2 0.347662 0.737987 -0.029195 11.00000 -1.50000 AFIX 0 C161 1 0.669680 0.425705 0.452368 11.00000 0.03136 0.03252 = 0.03289 0.00013 0.00921 -0.00080 C162 1 0.759642 0.473119 0.502031 11.00000 0.05946 0.03297 = 0.04036 0.00114 -0.00398 -0.00786 AFIX 43 H162 2 0.742573 0.507928 0.462458 11.00000 -1.20000 AFIX 0 C163 1 0.872745 0.470757 0.607121 11.00000 0.05877 0.04681 = 0.04296 -0.00897 -0.00066 -0.01464 AFIX 43 H163 2 0.931322 0.504086 0.638476 11.00000 -1.20000 AFIX 0 C164 1 0.903383 0.421733 0.667899 11.00000 0.03427 0.04718 = 0.03175 -0.00714 0.00439 0.00431 C165 1 0.805052 0.375054 0.623171 11.00000 0.05708 0.03685 = 0.03671 0.00055 -0.00208 0.00659 AFIX 43 H165 2 0.815159 0.341221 0.666340 11.00000 -1.20000 AFIX 0 C166 1 0.692650 0.376663 0.517162 11.00000 0.04855 0.03147 = 0.03931 -0.00205 -0.00188 -0.00082 AFIX 43 H166 2 0.629754 0.343632 0.487886 11.00000 -1.20000 AFIX 0 C167 1 1.037940 0.418195 0.778612 11.00000 0.04419 0.06182 = 0.04064 -0.00982 -0.00190 0.00242 AFIX 137 H16A 2 0.973016 0.422357 0.843873 11.00000 -1.50000 H16B 2 1.128709 0.448202 0.780758 11.00000 -1.50000 H16C 2 1.099684 0.381725 0.783273 11.00000 -1.50000 AFIX 0 HKLF 4 END ; _[local]_cod_data_source_file c4gc00881b2.cif _[local]_cod_data_source_block ly02 _cod_depositor_comments 'Adding full bibliography for 7216643.cif.' _cod_database_code 7216643 loop_ _symmetry_equiv_pos_as_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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags N11 N 0.5137(3) 0.37529(8) 0.28846(17) 0.0293(5) Uani 1 1 d . C12 C 0.4162(3) 0.37384(10) 0.1822(2) 0.0276(5) Uani 1 1 d . C13 C 0.3615(3) 0.42187(10) 0.1193(2) 0.0297(6) Uani 1 1 d . H13 H 0.2947 0.4187 0.0434 0.036 Uiso 1 1 calc R C14 C 0.4043(3) 0.47497(10) 0.1672(2) 0.0283(5) Uani 1 1 d . C15 C 0.5027(4) 0.47584(10) 0.2780(2) 0.0335(6) Uani 1 1 d . H15 H 0.533 0.5108 0.3151 0.04 Uiso 1 1 calc R C16 C 0.5580(3) 0.42602(10) 0.3356(2) 0.0302(6) Uani 1 1 d . C121 C 0.3676(3) 0.31637(10) 0.1336(2) 0.0278(5) Uani 1 1 d . C122 C 0.4055(4) 0.26883(11) 0.2022(2) 0.0351(6) Uani 1 1 d . H122 H 0.4654 0.2728 0.2796 0.042 Uiso 1 1 calc R C123 C 0.3570(4) 0.21575(11) 0.1592(2) 0.0364(6) Uani 1 1 d . H123 H 0.3835 0.1842 0.2082 0.044 Uiso 1 1 calc R C124 C 0.2715(3) 0.20761(11) 0.0473(2) 0.0337(6) Uani 1 1 d . C125 C 0.2354(3) 0.25469(11) -0.0216(2) 0.0337(6) Uani 1 1 d . H125 H 0.1779 0.2504 -0.0994 0.04 Uiso 1 1 calc R C126 C 0.2821(4) 0.30828(11) 0.0212(2) 0.0335(6) Uani 1 1 d . H126 H 0.2545 0.3398 -0.0279 0.04 Uiso 1 1 calc R C127 C 0.2185(4) 0.14980(11) -0.0002(3) 0.0423(7) Uani 1 1 d . H12A H 0.2685 0.1213 0.0564 0.063 Uiso 1 1 calc R H12B H 0.2677 0.144 -0.0714 0.063 Uiso 1 1 calc R H12C H 0.0849 0.1466 -0.0165 0.063 Uiso 1 1 calc R C141 C 0.3475(3) 0.52695(10) 0.1020(2) 0.0286(6) Uani 1 1 d . C142 C 0.2320(4) 0.52634(11) -0.0032(2) 0.0371(6) Uani 1 1 d . H142 H 0.1893 0.4912 -0.0348 0.045 Uiso 1 1 calc R C143 C 0.1758(4) 0.57423(11) -0.0641(2) 0.0370(6) Uani 1 1 d . H143 H 0.0989 0.5712 -0.137 0.044 Uiso 1 1 calc R C144 C 0.2305(3) 0.62750(11) -0.0204(2) 0.0335(6) Uani 1 1 d . C145 C 0.3486(4) 0.62854(11) 0.0854(2) 0.0367(6) Uani 1 1 d . H145 H 0.3911 0.6637 0.1175 0.044 Uiso 1 1 calc R C146 C 0.4051(4) 0.58004(10) 0.1445(2) 0.0342(6) Uani 1 1 d . H146 H 0.4855 0.5827 0.2162 0.041 Uiso 1 1 calc R N144 N 0.1704(3) 0.67566(9) -0.0781(2) 0.0430(6) Uani 1 1 d . C147 C 0.0839(4) 0.67395(12) -0.1969(3) 0.0444(7) Uani 1 1 d . H14A H 0.1658 0.6558 -0.2427 0.067 Uiso 1 1 calc R H14B H 0.0574 0.7123 -0.225 0.067 Uiso 1 1 calc R H14C H -0.0304 0.6526 -0.2039 0.067 Uiso 1 1 calc R C148 C 0.2192(4) 0.72990(11) -0.0260(3) 0.0475(8) Uani 1 1 d . H14D H 0.2011 0.7294 0.0544 0.071 Uiso 1 1 calc R H14E H 0.1416 0.759 -0.068 0.071 Uiso 1 1 calc R H14F H 0.3477 0.738 -0.0292 0.071 Uiso 1 1 calc R C161 C 0.6697(3) 0.42571(11) 0.4524(2) 0.0318(6) Uani 1 1 d . C162 C 0.7596(4) 0.47312(12) 0.5020(3) 0.0457(8) Uani 1 1 d . H162 H 0.7426 0.5079 0.4625 0.055 Uiso 1 1 calc R C163 C 0.8727(4) 0.47076(13) 0.6071(3) 0.0506(8) Uani 1 1 d . H163 H 0.9313 0.5041 0.6385 0.061 Uiso 1 1 calc R C164 C 0.9034(4) 0.42173(12) 0.6679(2) 0.0379(7) Uani 1 1 d . C165 C 0.8051(4) 0.37505(12) 0.6232(2) 0.0447(7) Uani 1 1 d . H165 H 0.8152 0.3412 0.6663 0.054 Uiso 1 1 calc R C166 C 0.6926(4) 0.37666(11) 0.5172(2) 0.0409(7) Uani 1 1 d . H166 H 0.6298 0.3436 0.4879 0.049 Uiso 1 1 calc R C167 C 1.0379(4) 0.41820(14) 0.7786(3) 0.0499(8) Uani 1 1 d . H16A H 0.973 0.4224 0.8439 0.075 Uiso 1 1 calc R H16B H 1.1287 0.4482 0.7808 0.075 Uiso 1 1 calc R H16C H 1.0997 0.3817 0.7833 0.075 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 N11 0.0283(11) 0.0287(11) 0.0309(12) -0.0003(9) 0.0046(9) -0.0017(8) C12 0.0252(12) 0.0290(13) 0.0304(13) -0.0004(10) 0.0097(10) 0.0008(10) C13 0.0299(13) 0.0308(14) 0.0286(13) -0.0004(10) 0.0057(10) -0.0001(10) C14 0.0272(12) 0.0290(13) 0.0303(13) -0.0001(10) 0.0094(10) 0.0018(10) C15 0.0405(15) 0.0249(13) 0.0346(15) -0.0032(10) 0.0044(12) -0.0037(11) C16 0.0307(13) 0.0289(13) 0.0317(14) -0.0004(10) 0.0076(10) -0.0031(10) C121 0.0245(12) 0.0279(13) 0.0320(13) 0.0005(10) 0.0080(10) 0.0017(10) C122 0.0403(15) 0.0326(14) 0.0307(14) -0.0018(11) 0.0016(11) 0.0004(11) C123 0.0423(15) 0.0286(14) 0.0380(15) 0.0040(11) 0.0064(12) 0.0018(11) C124 0.0317(13) 0.0319(14) 0.0387(15) -0.0037(11) 0.0090(11) -0.0019(11) C125 0.0328(14) 0.0341(14) 0.0325(14) -0.0035(11) 0.0006(11) -0.0016(11) C126 0.0354(14) 0.0297(14) 0.0341(14) 0.0009(11) 0.0022(11) -0.0005(11) C127 0.0446(16) 0.0353(15) 0.0472(17) -0.0052(13) 0.0083(13) -0.0047(12) C141 0.0295(13) 0.0272(13) 0.0301(13) -0.0016(10) 0.0075(10) 0.0015(10) C142 0.0474(16) 0.0258(13) 0.0374(15) -0.0032(11) 0.0048(12) -0.0017(11) C143 0.0406(15) 0.0349(15) 0.0336(15) -0.0003(11) 0.0007(12) 0.0010(12) C144 0.0294(13) 0.0318(14) 0.0406(15) 0.0027(11) 0.0092(11) 0.0041(10) C145 0.0386(15) 0.0239(13) 0.0465(17) -0.0023(11) 0.0043(13) -0.0008(11) C146 0.0340(14) 0.0296(14) 0.0369(15) 0.0012(11) -0.0002(11) -0.0008(11) N144 0.0444(14) 0.0299(12) 0.0511(15) 0.0060(10) -0.0019(11) 0.0041(10) C147 0.0389(15) 0.0397(16) 0.0537(19) 0.0134(14) 0.0055(14) 0.0064(12) C148 0.0427(16) 0.0283(15) 0.072(2) 0.0078(14) 0.0102(15) 0.0058(12) C161 0.0314(13) 0.0325(14) 0.0329(14) 0.0001(11) 0.0092(11) -0.0008(11) C162 0.0595(19) 0.0330(15) 0.0404(17) 0.0011(12) -0.0040(14) -0.0079(13) C163 0.059(2) 0.0468(18) 0.0430(18) -0.0090(14) -0.0007(15) -0.0146(15) C164 0.0343(14) 0.0472(17) 0.0318(14) -0.0071(12) 0.0044(11) 0.0043(12) C165 0.0571(18) 0.0368(16) 0.0367(16) 0.0006(12) -0.0021(14) 0.0066(13) C166 0.0486(17) 0.0315(14) 0.0393(16) -0.0020(12) -0.0019(13) -0.0008(12) C167 0.0442(17) 0.062(2) 0.0406(17) -0.0098(14) -0.0019(13) 0.0024(15) 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 0 '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 C12 N11 C16 117.7(2) N11 C12 C13 122.9(2) N11 C12 C121 115.9(2) C13 C12 C121 121.2(2) C12 C13 C14 120.3(2) C12 C13 H13 119.8 C14 C13 H13 119.8 C15 C14 C13 116.2(2) C15 C14 C141 122.3(2) C13 C14 C141 121.5(2) C14 C15 C16 120.8(2) C14 C15 H15 119.6 C16 C15 H15 119.6 N11 C16 C15 122.1(2) N11 C16 C161 116.0(2) C15 C16 C161 121.9(2) C126 C121 C122 117.2(2) C126 C121 C12 122.2(2) C122 C121 C12 120.5(2) C123 C122 C121 121.0(2) C123 C122 H122 119.5 C121 C122 H122 119.5 C124 C123 C122 121.9(2) C124 C123 H123 119.1 C122 C123 H123 119.1 C123 C124 C125 117.4(2) C123 C124 C127 122.1(2) C125 C124 C127 120.5(2) C124 C125 C126 121.2(2) C124 C125 H125 119.4 C126 C125 H125 119.4 C121 C126 C125 121.3(2) C121 C126 H126 119.3 C125 C126 H126 119.3 C124 C127 H12A 109.5 C124 C127 H12B 109.5 H12A C127 H12B 109.5 C124 C127 H12C 109.5 H12A C127 H12C 109.5 H12B C127 H12C 109.5 C142 C141 C146 115.8(2) C142 C141 C14 122.3(2) C146 C141 C14 121.9(2) C143 C142 C141 123.1(2) C143 C142 H142 118.4 C141 C142 H142 118.4 C142 C143 C144 121.0(2) C142 C143 H143 119.5 C144 C143 H143 119.5 N144 C144 C145 122.0(2) N144 C144 C143 121.7(2) C145 C144 C143 116.2(2) C146 C145 C144 121.8(2) C146 C145 H145 119.1 C144 C145 H145 119.1 C145 C146 C141 121.9(2) C145 C146 H146 119 C141 C146 H146 119 C144 N144 C147 120.9(2) C144 N144 C148 120.0(2) C147 N144 C148 118.4(2) N144 C147 H14A 109.5 N144 C147 H14B 109.5 H14A C147 H14B 109.5 N144 C147 H14C 109.5 H14A C147 H14C 109.5 H14B C147 H14C 109.5 N144 C148 H14D 109.5 N144 C148 H14E 109.5 H14D C148 H14E 109.5 N144 C148 H14F 109.5 H14D C148 H14F 109.5 H14E C148 H14F 109.5 C162 C161 C166 116.5(2) C162 C161 C16 122.7(2) C166 C161 C16 120.8(2) C163 C162 C161 121.5(3) C163 C162 H162 119.3 C161 C162 H162 119.3 C164 C163 C162 121.9(3) C164 C163 H163 119.1 C162 C163 H163 119.1 C163 C164 C165 117.1(3) C163 C164 C167 121.9(3) C165 C164 C167 121.0(3) C166 C165 C164 121.4(3) C166 C165 H165 119.3 C164 C165 H165 119.3 C165 C166 C161 121.3(3) C165 C166 H166 119.3 C161 C166 H166 119.3 C164 C167 H16A 109.5 C164 C167 H16B 109.5 H16A C167 H16B 109.5 C164 C167 H16C 109.5 H16A C167 H16C 109.5 H16B C167 H16C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N11 C12 1.337(3) N11 C16 1.348(3) C12 C13 1.387(3) C12 C121 1.505(3) C13 C14 1.400(3) C13 H13 0.95 C14 C15 1.384(3) C14 C141 1.481(3) C15 C16 1.395(3) C15 H15 0.95 C16 C161 1.481(3) C121 C126 1.383(3) C121 C122 1.393(3) C122 C123 1.388(4) C122 H122 0.95 C123 C124 1.377(4) C123 H123 0.95 C124 C125 1.385(4) C124 C127 1.515(4) C125 C126 1.395(3) C125 H125 0.95 C126 H126 0.95 C127 H12A 0.98 C127 H12B 0.98 C127 H12C 0.98 C141 C142 1.384(3) C141 C146 1.401(3) C142 C143 1.375(4) C142 H142 0.95 C143 C144 1.404(4) C143 H143 0.95 C144 N144 1.370(3) C144 C145 1.399(4) C145 C146 1.378(3) C145 H145 0.95 C146 H146 0.95 N144 C147 1.439(4) N144 C148 1.451(4) C147 H14A 0.98 C147 H14B 0.98 C147 H14C 0.98 C148 H14D 0.98 C148 H14E 0.98 C148 H14F 0.98 C161 C162 1.391(4) C161 C166 1.391(4) C162 C163 1.375(4) C162 H162 0.95 C163 C164 1.370(4) C163 H163 0.95 C164 C165 1.385(4) C164 C167 1.506(4) C165 C166 1.381(4) C165 H165 0.95 C166 H166 0.95 C167 H16A 0.98 C167 H16B 0.98 C167 H16C 0.98