# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Russell Johnstone' _publ_contact_author_email R.D.L.JOHNSTONE@SMS.ED.AC.UK _publ_section_title ; Use of the Allen Key in Crystal Engineering: Pressure-Induced Polymorphism in a High Z' Structure ; loop_ _publ_author_name 'Russell Johnstone' 'Alistair Lennie' 'Maria Leva' 'H McNab' 'Simon Parsons' 'Elna Pidcock' ; J.E.Warren ; # Attachment 'all.cif' data_ambient_150K.cif _database_code_depnum_ccdc_archive 'CCDC 745425' #_oxford_structure_analysis_title 'sp9016_150K in Pn' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 7.6168(2) _cell_length_b 15.2552(5) _cell_length_c 52.3376(16) _cell_angle_alpha 90 _cell_angle_beta 89.976(2) _cell_angle_gamma 90 _cell_volume 6081.4(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 n 1 ' _symmetry_space_group_name_Hall 'P -2yac' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y,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 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 16 # Given Formula = C20 H15 N1 O2 # Dc = 1.32 Fooo = 2528.00 Mu = 0.85 M = 2410.76 # Found Formula = C20 H15 N1 O2 # Dc = 1.32 FOOO = 2528.00 Mu = 0.85 M = 2410.76 _chemical_formula_sum 'C20 H15 N1 O2' _chemical_formula_moiety 'C20 H15 N1 O2' _chemical_compound_source ? _chemical_formula_weight 301.34 _cell_measurement_reflns_used 9868 _cell_measurement_theta_min 3 _cell_measurement_theta_max 23 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.52 _exptl_crystal_size_mid 0.53 _exptl_crystal_size_max 0.67 _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 2528 _exptl_absorpt_coefficient_mu 0.085 # Sheldrick geometric approximatio 0.96 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.83 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device 'Bruker SMART' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 39621 _reflns_number_total 8753 _diffrn_reflns_av_R_equivalents 0.0497 # Number of reflections with Friedels Law is 8753 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 8771 _diffrn_reflns_reduction_process ; Merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 ; _diffrn_reflns_theta_min 1.335 _diffrn_reflns_theta_max 23.283 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 23.283 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 58 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 58 #_oxford_diffrn_Wilson_B_factor 0.00 #_oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.14 _refine_diff_density_max 0.13 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement #_oxford_reflns_threshold_expression_ref I>2.0\s(I) _refine_ls_number_reflns 8633 _refine_ls_number_restraints 3082 _refine_ls_number_parameters 1658 #_oxford_refine_ls_R_factor_ref 0.0365 _refine_ls_wR_factor_ref 0.0241 _refine_ls_goodness_of_fit_ref 1.0526 _refine_ls_shift/su_max 0.008442 # The values computed from all data #_oxford_reflns_number_all 8685 _refine_ls_R_factor_all 0.0369 _refine_ls_wR_factor_all 0.0242 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 8633 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_gt 0.0241 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 2.11 -1.90 1.23 ; 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens N11 N -0.0759(5) 0.71651(19) -0.14403(6) 0.0255 1.0000 Uani D U . . . . . O11 O 0.0994(4) 0.6812(2) -0.09667(6) 0.0367 1.0000 Uani D U . . . . . O21 O -0.0907(4) 0.7150(2) -0.06526(5) 0.0344 1.0000 Uani D U . . . . . C121 C -0.0055(4) 0.8004(2) -0.14139(6) 0.0233 1.0000 Uani D U . . . . . C111 C -0.0570(4) 0.8691(2) -0.12562(6) 0.0286 1.0000 Uani D U . . . . . C101 C 0.0330(5) 0.94725(19) -0.12751(6) 0.0285 1.0000 Uani D U . . . . . C91 C 0.1707(5) 0.95776(19) -0.14459(7) 0.0281 1.0000 Uani D U . . . . . C81 C 0.2218(5) 0.8899(2) -0.16016(7) 0.0260 1.0000 Uani D U . . . . . C71 C 0.1353(5) 0.8101(2) -0.15872(6) 0.0225 1.0000 Uani D U . . . . . C61 C 0.1527(5) 0.7274(3) -0.17237(7) 0.0225 1.0000 Uani D U . . . . . C51 C 0.2659(6) 0.6968(3) -0.19130(8) 0.0324 1.0000 Uani D U . . . . . C41 C 0.2476(7) 0.6121(3) -0.19976(8) 0.0352 1.0000 Uani D U . . . . . C31 C 0.1189(6) 0.5570(3) -0.18953(8) 0.0301 1.0000 Uani D U . . . . . C21 C 0.0045(6) 0.5862(3) -0.17099(7) 0.0286 1.0000 Uani D U . . . . . C11 C 0.0243(6) 0.6719(2) -0.16269(7) 0.0224 1.0000 Uani D U . . . . . C131 C -0.2186(6) 0.6805(2) -0.13043(8) 0.0225 1.0000 Uani D U . . . . . C141 C -0.2119(6) 0.6677(2) -0.10384(8) 0.0205 1.0000 Uani D U . . . . . C151 C -0.3571(6) 0.6331(2) -0.09153(8) 0.0271 1.0000 Uani D U . . . . . C161 C -0.5054(6) 0.6112(2) -0.10495(9) 0.0313 1.0000 Uani D U . . . . . C171 C -0.5149(6) 0.6249(2) -0.13114(8) 0.0321 1.0000 Uani D U . . . . . C181 C -0.3702(6) 0.6601(2) -0.14365(8) 0.0283 1.0000 Uani D U . . . . . C191 C -0.0490(6) 0.6876(2) -0.08919(7) 0.0237 1.0000 Uani D U . . . . . C201 C 0.0610(7) 0.7382(3) -0.04960(8) 0.0411 1.0000 Uani D U . . . . . N12 N 0.0477(5) 0.2720(2) 0.00845(6) 0.0257 1.0000 Uani D U . . . . . O12 O -0.1352(5) 0.2149(2) -0.03443(6) 0.0403 1.0000 Uani D U . . . . . O22 O 0.0336(4) 0.19547(19) -0.06927(5) 0.0332 1.0000 Uani D U . . . . . C12 C -0.0221(4) 0.3546(2) 0.00404(6) 0.0247 1.0000 Uani D U . . . . . C22 C 0.0296(4) 0.4189(2) -0.01299(6) 0.0293 1.0000 Uani D U . . . . . C32 C -0.0591(5) 0.4972(2) -0.01263(6) 0.0352 1.0000 Uani D U . . . . . C42 C -0.1975(5) 0.51208(19) 0.00434(7) 0.0367 1.0000 Uani D U . . . . . C52 C -0.2500(5) 0.4476(2) 0.02124(7) 0.0344 1.0000 Uani D U . . . . . C62 C -0.1619(6) 0.3681(2) 0.02142(7) 0.0265 1.0000 Uani D U . . . . . C72 C -0.1820(5) 0.2883(3) 0.03566(7) 0.0254 1.0000 Uani D U . . . . . C82 C -0.2969(6) 0.2591(3) 0.05517(8) 0.0288 1.0000 Uani D U . . . . . C92 C -0.2808(6) 0.1750(3) 0.06426(8) 0.0320 1.0000 Uani D U . . . . . C102 C -0.1499(6) 0.1178(3) 0.05463(7) 0.0299 1.0000 Uani D U . . . . . C112 C -0.0362(6) 0.1448(3) 0.03574(7) 0.0258 1.0000 Uani D U . . . . . C122 C -0.0496(6) 0.2298(3) 0.02690(7) 0.0250 1.0000 Uani D U . . . . . C132 C 0.1928(6) 0.2328(2) -0.00519(8) 0.0233 1.0000 Uani D U . . . . . C142 C 0.1745(6) 0.1977(2) -0.02947(8) 0.0206 1.0000 Uani D U . . . . . C152 C 0.3206(6) 0.1578(2) -0.04053(8) 0.0242 1.0000 Uani D U . . . . . C162 C 0.4796(6) 0.1510(2) -0.02754(8) 0.0278 1.0000 Uani D U . . . . . C172 C 0.4953(6) 0.1870(2) -0.00332(8) 0.0309 1.0000 Uani D U . . . . . C182 C 0.3517(6) 0.2277(3) 0.00766(8) 0.0282 1.0000 Uani D U . . . . . C192 C 0.0082(6) 0.2044(3) -0.04409(7) 0.0243 1.0000 Uani D U . . . . . C202 C -0.1226(7) 0.2002(3) -0.08483(9) 0.0394 1.0000 Uani D U . . . . . N13 N 0.5379(5) 0.3737(2) 0.11258(6) 0.0247 1.0000 Uani D U . . . . . O13 O 0.3747(4) 0.4006(2) 0.16252(6) 0.0327 1.0000 Uani D U . . . . . O23 O 0.5680(4) 0.34523(17) 0.19011(5) 0.0276 1.0000 Uani D U . . . . . C13 C 0.4675(4) 0.28987(19) 0.11466(6) 0.0175 1.0000 Uani D U . . . . . C23 C 0.5188(4) 0.2205(2) 0.12977(6) 0.0230 1.0000 Uani D U . . . . . C33 C 0.4328(5) 0.14214(18) 0.12692(6) 0.0219 1.0000 Uani D U . . . . . C43 C 0.2973(5) 0.13191(19) 0.10919(7) 0.0269 1.0000 Uani D U . . . . . C53 C 0.2451(5) 0.2006(2) 0.09424(7) 0.0258 1.0000 Uani D U . . . . . C63 C 0.3299(5) 0.2818(2) 0.09695(6) 0.0204 1.0000 Uani D U . . . . . C73 C 0.3132(5) 0.3653(3) 0.08388(7) 0.0223 1.0000 Uani D U . . . . . C83 C 0.2027(6) 0.3969(3) 0.06463(8) 0.0270 1.0000 Uani D U . . . . . C93 C 0.2266(6) 0.4798(3) 0.05569(8) 0.0346 1.0000 Uani D U . . . . . C103 C 0.3607(6) 0.5334(3) 0.06580(8) 0.0330 1.0000 Uani D U . . . . . C113 C 0.4693(6) 0.5043(3) 0.08463(8) 0.0297 1.0000 Uani D U . . . . . C123 C 0.4467(6) 0.4207(2) 0.09367(7) 0.0209 1.0000 Uani D U . . . . . C133 C 0.6834(6) 0.4081(2) 0.12661(8) 0.0227 1.0000 Uani D U . . . . . C143 C 0.6801(5) 0.4113(2) 0.15315(8) 0.0213 1.0000 Uani D U . . . . . C153 C 0.8287(6) 0.4437(2) 0.16574(8) 0.0243 1.0000 Uani D U . . . . . C163 C 0.9738(6) 0.4723(2) 0.15243(9) 0.0271 1.0000 Uani D U . . . . . C173 C 0.9751(6) 0.4678(2) 0.12569(9) 0.0295 1.0000 Uani D U . . . . . C183 C 0.8304(6) 0.4353(3) 0.11335(9) 0.0271 1.0000 Uani D U . . . . . C193 C 0.5237(6) 0.3867(2) 0.16835(8) 0.0214 1.0000 Uani D U . . . . . C203 C 0.4276(7) 0.3146(3) 0.20599(8) 0.0323 1.0000 Uani D U . . . . . N14 N -0.0694(4) 0.18337(19) 0.25132(6) 0.0206 1.0000 Uani D U . . . . . O14 O 0.0941(4) 0.1568(2) 0.20098(6) 0.0333 1.0000 Uani D U . . . . . O24 O -0.1030(4) 0.21084(19) 0.17360(5) 0.0305 1.0000 Uani D U . . . . . C124 C -0.0006(4) 0.2676(2) 0.24949(6) 0.0237 1.0000 Uani D U . . . . . C114 C -0.0523(4) 0.3375(2) 0.23430(6) 0.0229 1.0000 Uani D U . . . . . C104 C 0.0346(5) 0.41605(19) 0.23720(6) 0.0264 1.0000 Uani D U . . . . . C94 C 0.1700(5) 0.42570(19) 0.25480(7) 0.0280 1.0000 Uani D U . . . . . C84 C 0.2235(5) 0.3562(2) 0.26945(7) 0.0270 1.0000 Uani D U . . . . . C74 C 0.1380(5) 0.2760(2) 0.26717(7) 0.0245 1.0000 Uani D U . . . . . C64 C 0.1540(5) 0.1936(3) 0.27999(7) 0.0228 1.0000 Uani D U . . . . . C54 C 0.2635(6) 0.1611(3) 0.29905(8) 0.0312 1.0000 Uani D U . . . . . C44 C 0.2386(6) 0.0774(3) 0.30780(8) 0.0341 1.0000 Uani D U . . . . . C34 C 0.1108(6) 0.0223(3) 0.29794(8) 0.0337 1.0000 Uani D U . . . . . C24 C 0.0005(6) 0.0528(2) 0.27854(7) 0.0229 1.0000 Uani D U . . . . . C14 C 0.0220(6) 0.1373(2) 0.27001(7) 0.0221 1.0000 Uani D U . . . . . C134 C -0.2140(5) 0.1495(2) 0.23695(8) 0.0216 1.0000 Uani D U . . . . . C144 C -0.2140(6) 0.1452(2) 0.21047(8) 0.0208 1.0000 Uani D U . . . . . C154 C -0.3612(6) 0.1135(2) 0.19788(8) 0.0254 1.0000 Uani D U . . . . . C164 C -0.5056(6) 0.0851(2) 0.21156(9) 0.0291 1.0000 Uani D U . . . . . C174 C -0.5052(6) 0.0895(2) 0.23749(9) 0.0299 1.0000 Uani D U . . . . . C184 C -0.3627(6) 0.1215(2) 0.25048(8) 0.0288 1.0000 Uani D U . . . . . C194 C -0.0553(6) 0.1710(3) 0.19533(8) 0.0229 1.0000 Uani D U . . . . . C204 C 0.0379(7) 0.2421(3) 0.15770(8) 0.0313 1.0000 Uani D U . . . . . N15 N 0.0502(5) 0.1357(2) 0.49599(6) 0.0257 1.0000 Uani D U . . . . . O15 O -0.1198(4) 0.0904(2) 0.44761(6) 0.0360 1.0000 Uani D U . . . . . O25 O 0.0757(4) 0.13480(17) 0.41818(5) 0.0254 1.0000 Uani D U . . . . . C15 C -0.0138(4) 0.2196(2) 0.49167(7) 0.0296 1.0000 Uani D U . . . . . C25 C 0.0451(4) 0.2840(2) 0.47504(6) 0.0285 1.0000 Uani D U . . . . . C35 C -0.0314(5) 0.3651(2) 0.47639(6) 0.0318 1.0000 Uani D U . . . . . C45 C -0.1662(5) 0.38278(19) 0.49365(7) 0.0310 1.0000 Uani D U . . . . . C55 C -0.2267(5) 0.3191(2) 0.50969(7) 0.0289 1.0000 Uani D U . . . . . C65 C -0.1503(6) 0.2362(2) 0.50909(6) 0.0269 1.0000 Uani D U . . . . . C75 C -0.1721(6) 0.1572(3) 0.52421(8) 0.0280 1.0000 Uani D U . . . . . C85 C -0.2842(6) 0.1334(3) 0.54413(8) 0.0352 1.0000 Uani D U . . . . . C95 C -0.2668(7) 0.0532(3) 0.55566(8) 0.0394 1.0000 Uani D U . . . . . C105 C -0.1398(6) -0.0057(3) 0.54706(8) 0.0365 1.0000 Uani D U . . . . . C115 C -0.0268(6) 0.0145(3) 0.52711(8) 0.0311 1.0000 Uani D U . . . . . C125 C -0.0487(6) 0.0980(3) 0.51569(7) 0.0272 1.0000 Uani D U . . . . . C135 C 0.1948(6) 0.0952(2) 0.48281(8) 0.0268 1.0000 Uani D U . . . . . C145 C 0.1899(6) 0.0825(2) 0.45667(8) 0.0209 1.0000 Uani D U . . . . . C155 C 0.3377(6) 0.0473(2) 0.44457(8) 0.0254 1.0000 Uani D U . . . . . C165 C 0.4853(6) 0.0239(2) 0.45878(8) 0.0307 1.0000 Uani D U . . . . . C175 C 0.4854(7) 0.0379(2) 0.48440(9) 0.0333 1.0000 Uani D U . . . . . C185 C 0.3425(6) 0.0733(2) 0.49689(9) 0.0307 1.0000 Uani D U . . . . . C195 C 0.0306(6) 0.1028(2) 0.44121(7) 0.0214 1.0000 Uani D U . . . . . C205 C -0.0732(6) 0.1591(3) 0.40166(8) 0.0323 1.0000 Uani D U . . . . . N16 N 0.5660(4) 0.21072(19) 0.61092(6) 0.0200 1.0000 Uani D U . . . . . O16 O 0.3752(4) 0.2885(2) 0.65002(6) 0.0371 1.0000 Uani D U . . . . . O26 O 0.5375(4) 0.32486(18) 0.68380(5) 0.0279 1.0000 Uani D U . . . . . C16 C 0.5102(4) 0.12896(19) 0.61889(6) 0.0217 1.0000 Uani D U . . . . . C26 C 0.5752(4) 0.0756(2) 0.63801(6) 0.0260 1.0000 Uani D U . . . . . C36 C 0.4971(5) -0.0036(2) 0.64179(6) 0.0322 1.0000 Uani D U . . . . . C46 C 0.3546(5) -0.03093(17) 0.62696(7) 0.0289 1.0000 Uani D U . . . . . C56 C 0.2876(5) 0.0220(2) 0.60829(7) 0.0287 1.0000 Uani D U . . . . . C66 C 0.3637(5) 0.1034(2) 0.60400(6) 0.0193 1.0000 Uani D U . . . . . C76 C 0.3310(5) 0.1756(3) 0.58631(7) 0.0240 1.0000 Uani D U . . . . . C86 C 0.2088(6) 0.1900(3) 0.56666(8) 0.0330 1.0000 Uani D U . . . . . C96 C 0.2137(6) 0.2673(3) 0.55403(8) 0.0344 1.0000 Uani D U . . . . . C106 C 0.3365(6) 0.3328(3) 0.55981(8) 0.0348 1.0000 Uani D U . . . . . C116 C 0.4603(7) 0.3200(3) 0.57896(8) 0.0335 1.0000 Uani D U . . . . . C126 C 0.4546(5) 0.2410(3) 0.59174(7) 0.0206 1.0000 Uani D U . . . . . C136 C 0.7067(6) 0.2596(2) 0.62187(8) 0.0199 1.0000 Uani D U . . . . . C146 C 0.6853(6) 0.3049(2) 0.64492(7) 0.0191 1.0000 Uani D U . . . . . C156 C 0.8284(6) 0.3515(2) 0.65441(8) 0.0257 1.0000 Uani D U . . . . . C166 C 0.9871(6) 0.3520(2) 0.64168(8) 0.0275 1.0000 Uani D U . . . . . C176 C 1.0053(6) 0.3052(2) 0.61965(8) 0.0264 1.0000 Uani D U . . . . . C186 C 0.8678(6) 0.2592(2) 0.60963(8) 0.0234 1.0000 Uani D U . . . . . C196 C 0.5163(6) 0.3044(2) 0.65892(8) 0.0207 1.0000 Uani D U . . . . . C206 C 0.3809(6) 0.3271(3) 0.69919(8) 0.0343 1.0000 Uani D U . . . . . N17 N -0.1068(4) 0.23247(18) 0.75067(6) 0.0205 1.0000 Uani D U . . . . . O17 O 0.0824(4) 0.1549(2) 0.71167(5) 0.0353 1.0000 Uani D U . . . . . O27 O -0.0793(4) 0.11719(18) 0.67800(5) 0.0295 1.0000 Uani D U . . . . . C17 C -0.0005(4) 0.20210(18) 0.77018(6) 0.0187 1.0000 Uani D U . . . . . C27 C -0.0011(4) 0.12202(19) 0.78257(6) 0.0247 1.0000 Uani D U . . . . . C37 C 0.1209(5) 0.10831(19) 0.80138(7) 0.0325 1.0000 Uani D U . . . . . C47 C 0.2447(5) 0.1723(2) 0.80771(6) 0.0374 1.0000 Uani D U . . . . . C57 C 0.2485(5) 0.2512(2) 0.79497(6) 0.0276 1.0000 Uani D U . . . . . C67 C 0.1289(5) 0.26687(19) 0.77579(6) 0.0235 1.0000 Uani D U . . . . . C77 C 0.0958(5) 0.3387(3) 0.75841(7) 0.0225 1.0000 Uani D U . . . . . C87 C 0.1749(5) 0.4205(3) 0.75416(8) 0.0276 1.0000 Uani D U . . . . . C97 C 0.1069(6) 0.4733(3) 0.73516(8) 0.0324 1.0000 Uani D U . . . . . C107 C -0.0346(6) 0.4479(2) 0.72017(8) 0.0287 1.0000 Uani D U . . . . . C117 C -0.1160(5) 0.3677(2) 0.72401(7) 0.0224 1.0000 Uani D U . . . . . C127 C -0.0508(5) 0.3142(2) 0.74318(7) 0.0188 1.0000 Uani D U . . . . . C137 C -0.2482(5) 0.1831(2) 0.73960(7) 0.0189 1.0000 Uani D U . . . . . C147 C -0.2262(5) 0.1374(2) 0.71698(7) 0.0205 1.0000 Uani D U . . . . . C157 C -0.3692(6) 0.0902(2) 0.70743(7) 0.0239 1.0000 Uani D U . . . . . C167 C -0.5281(6) 0.0898(2) 0.72010(8) 0.0268 1.0000 Uani D U . . . . . C177 C -0.5484(6) 0.1371(2) 0.74246(8) 0.0265 1.0000 Uani D U . . . . . C187 C -0.4063(5) 0.1840(2) 0.75213(8) 0.0237 1.0000 Uani D U . . . . . C197 C -0.0570(6) 0.1372(3) 0.70256(7) 0.0222 1.0000 Uani D U . . . . . C207 C 0.0790(7) 0.1167(3) 0.66260(9) 0.0373 1.0000 Uani D U . . . . . N18 N 0.3963(4) 0.30681(19) 0.86536(6) 0.0249 1.0000 Uani D U . . . . . O18 O 0.5757(4) 0.3695(2) 0.90768(5) 0.0370 1.0000 Uani D U . . . . . O28 O 0.4028(4) 0.39267(19) 0.94148(5) 0.0326 1.0000 Uani D U . . . . . C18 C 0.5003(4) 0.33935(19) 0.84587(6) 0.0227 1.0000 Uani D U . . . . . C28 C 0.4931(4) 0.41921(19) 0.83347(6) 0.0251 1.0000 Uani D U . . . . . C38 C 0.6119(5) 0.43472(19) 0.81408(7) 0.0322 1.0000 Uani D U . . . . . C48 C 0.7381(5) 0.3727(2) 0.80733(6) 0.0343 1.0000 Uani D U . . . . . C58 C 0.7456(5) 0.2926(2) 0.81965(7) 0.0288 1.0000 Uani D U . . . . . C68 C 0.6253(5) 0.27544(19) 0.83949(7) 0.0247 1.0000 Uani D U . . . . . C78 C 0.5949(6) 0.2008(3) 0.85571(7) 0.0241 1.0000 Uani D U . . . . . C88 C 0.6724(6) 0.1170(3) 0.85823(8) 0.0283 1.0000 Uani D U . . . . . C98 C 0.6025(6) 0.0615(3) 0.87645(8) 0.0286 1.0000 Uani D U . . . . . C108 C 0.4638(6) 0.0855(3) 0.89193(7) 0.0286 1.0000 Uani D U . . . . . C118 C 0.3870(6) 0.1672(2) 0.88973(7) 0.0245 1.0000 Uani D U . . . . . C128 C 0.4545(5) 0.2241(2) 0.87144(7) 0.0214 1.0000 Uani D U . . . . . C138 C 0.2523(6) 0.3533(2) 0.87686(7) 0.0217 1.0000 Uani D U . . . . . C148 C 0.2655(5) 0.3876(2) 0.90147(7) 0.0205 1.0000 Uani D U . . . . . C158 C 0.1194(6) 0.4303(2) 0.91202(8) 0.0274 1.0000 Uani D U . . . . . C168 C -0.0348(6) 0.4375(2) 0.89775(8) 0.0319 1.0000 Uani D U . . . . . C178 C -0.0477(6) 0.4035(2) 0.87374(8) 0.0302 1.0000 Uani D U . . . . . C188 C 0.0973(6) 0.3608(3) 0.86331(8) 0.0286 1.0000 Uani D U . . . . . C198 C 0.4307(6) 0.3818(2) 0.91669(7) 0.0239 1.0000 Uani D U . . . . . C208 C 0.5587(7) 0.3890(3) 0.95710(9) 0.0478 1.0000 Uani D U . . . . . H1111 H -0.1511 0.8623 -0.1139 0.0338 1.0000 Uiso R . . . . . . H1011 H -0.0002 0.9950 -0.1169 0.0340 1.0000 Uiso R . . . . . . H911 H 0.2303 1.0124 -0.1455 0.0340 1.0000 Uiso R . . . . . . H811 H 0.3159 0.8975 -0.1719 0.0315 1.0000 Uiso R . . . . . . H511 H 0.3541 0.7340 -0.1982 0.0390 1.0000 Uiso R . . . . . . H411 H 0.3235 0.5908 -0.2128 0.0425 1.0000 Uiso R . . . . . . H311 H 0.1104 0.4983 -0.1954 0.0367 1.0000 Uiso R . . . . . . H211 H -0.0843 0.5492 -0.1642 0.0344 1.0000 Uiso R . . . . . . H1511 H -0.3538 0.6242 -0.0736 0.0325 1.0000 Uiso R . . . . . . H1611 H -0.6029 0.5866 -0.0962 0.0378 1.0000 Uiso R . . . . . . H1711 H -0.6184 0.6103 -0.1403 0.0387 1.0000 Uiso R . . . . . . H1811 H -0.3756 0.6704 -0.1615 0.0339 1.0000 Uiso R . . . . . . H2011 H 0.0209 0.7573 -0.0327 0.0495 1.0000 Uiso R . . . . . . H2012 H 0.1261 0.7859 -0.0578 0.0495 1.0000 Uiso R . . . . . . H2013 H 0.1377 0.6870 -0.0478 0.0495 1.0000 Uiso R . . . . . . H221 H 0.1238 0.4091 -0.0246 0.0352 1.0000 Uiso R . . . . . . H321 H -0.0258 0.5422 -0.0242 0.0420 1.0000 Uiso R . . . . . . H421 H -0.2561 0.5671 0.0043 0.0442 1.0000 Uiso R . . . . . . H521 H -0.3453 0.4575 0.0326 0.0411 1.0000 Uiso R . . . . . . H821 H -0.3838 0.2973 0.0619 0.0345 1.0000 Uiso R . . . . . . H921 H -0.3586 0.1548 0.0772 0.0380 1.0000 Uiso R . . . . . . H1021 H -0.1404 0.0600 0.0613 0.0360 1.0000 Uiso R . . . . . . H1121 H 0.0494 0.1059 0.0290 0.0311 1.0000 Uiso R . . . . . . H1521 H 0.3116 0.1346 -0.0573 0.0289 1.0000 Uiso R . . . . . . H1621 H 0.5765 0.1220 -0.0352 0.0331 1.0000 Uiso R . . . . . . H1721 H 0.6037 0.1838 0.0056 0.0368 1.0000 Uiso R . . . . . . H1821 H 0.3619 0.2526 0.0242 0.0336 1.0000 Uiso R . . . . . . H2021 H -0.0907 0.1930 -0.1028 0.0477 1.0000 Uiso R . . . . . . H2022 H -0.1795 0.2572 -0.0824 0.0477 1.0000 Uiso R . . . . . . H2023 H -0.2036 0.1534 -0.0798 0.0477 1.0000 Uiso R . . . . . . H231 H 0.6115 0.2267 0.1418 0.0279 1.0000 Uiso R . . . . . . H331 H 0.4660 0.0937 0.1372 0.0259 1.0000 Uiso R . . . . . . H431 H 0.2407 0.0767 0.1075 0.0324 1.0000 Uiso R . . . . . . H531 H 0.1528 0.1935 0.0822 0.0308 1.0000 Uiso R . . . . . . H831 H 0.1125 0.3608 0.0578 0.0320 1.0000 Uiso R . . . . . . H931 H 0.1525 0.5018 0.0426 0.0416 1.0000 Uiso R . . . . . . H1031 H 0.3755 0.5910 0.0593 0.0390 1.0000 Uiso R . . . . . . H1131 H 0.5585 0.5411 0.0914 0.0351 1.0000 Uiso R . . . . . . H1531 H 0.8296 0.4460 0.1839 0.0291 1.0000 Uiso R . . . . . . H1631 H 1.0725 0.4951 0.1613 0.0328 1.0000 Uiso R . . . . . . H1731 H 1.0746 0.4868 0.1163 0.0354 1.0000 Uiso R . . . . . . H1831 H 0.8314 0.4313 0.0952 0.0326 1.0000 Uiso R . . . . . . H2031 H 0.4759 0.2857 0.2212 0.0388 1.0000 Uiso R . . . . . . H2032 H 0.3550 0.3644 0.2113 0.0388 1.0000 Uiso R . . . . . . H2033 H 0.3556 0.2728 0.1964 0.0388 1.0000 Uiso R . . . . . . H1141 H -0.1451 0.3314 0.2223 0.0273 1.0000 Uiso R . . . . . . H1041 H 0.0015 0.4646 0.2269 0.0318 1.0000 Uiso R . . . . . . H941 H 0.2259 0.4810 0.2567 0.0334 1.0000 Uiso R . . . . . . H841 H 0.3184 0.3626 0.2811 0.0326 1.0000 Uiso R . . . . . . H541 H 0.3546 0.1965 0.3059 0.0379 1.0000 Uiso R . . . . . . H441 H 0.3113 0.0562 0.3212 0.0415 1.0000 Uiso R . . . . . . H341 H 0.0982 -0.0357 0.3043 0.0411 1.0000 Uiso R . . . . . . H241 H -0.0873 0.0160 0.2714 0.0277 1.0000 Uiso R . . . . . . H1541 H -0.3625 0.1111 0.1797 0.0304 1.0000 Uiso R . . . . . . H1641 H -0.6053 0.0626 0.2028 0.0346 1.0000 Uiso R . . . . . . H1741 H -0.6050 0.0700 0.2468 0.0362 1.0000 Uiso R . . . . . . H1841 H -0.3645 0.1248 0.2686 0.0338 1.0000 Uiso R . . . . . . H2041 H -0.0111 0.2699 0.1424 0.0377 1.0000 Uiso R . . . . . . H2042 H 0.1079 0.2850 0.1672 0.0377 1.0000 Uiso R . . . . . . H2043 H 0.1126 0.1927 0.1527 0.0377 1.0000 Uiso R . . . . . . H251 H 0.1359 0.2721 0.4631 0.0343 1.0000 Uiso R . . . . . . H351 H 0.0081 0.4102 0.4653 0.0378 1.0000 Uiso R . . . . . . H451 H -0.2162 0.4398 0.4943 0.0372 1.0000 Uiso R . . . . . . H551 H -0.3202 0.3312 0.5212 0.0348 1.0000 Uiso R . . . . . . H851 H -0.3731 0.1728 0.5497 0.0417 1.0000 Uiso R . . . . . . H951 H -0.3407 0.0378 0.5696 0.0469 1.0000 Uiso R . . . . . . H1051 H -0.1306 -0.0615 0.5550 0.0440 1.0000 Uiso R . . . . . . H1151 H 0.0606 -0.0254 0.5214 0.0375 1.0000 Uiso R . . . . . . H1551 H 0.3377 0.0393 0.4266 0.0306 1.0000 Uiso R . . . . . . H1651 H 0.5846 -0.0014 0.4506 0.0364 1.0000 Uiso R . . . . . . H1751 H 0.5868 0.0227 0.4940 0.0397 1.0000 Uiso R . . . . . . H1851 H 0.3452 0.0826 0.5148 0.0365 1.0000 Uiso R . . . . . . H2051 H -0.0283 0.1817 0.3854 0.0377 1.0000 Uiso R . . . . . . H2052 H -0.1436 0.2045 0.4101 0.0377 1.0000 Uiso R . . . . . . H2053 H -0.1463 0.1074 0.3985 0.0377 1.0000 Uiso R . . . . . . H261 H 0.6715 0.0938 0.6482 0.0309 1.0000 Uiso R . . . . . . H361 H 0.5405 -0.0411 0.6548 0.0384 1.0000 Uiso R . . . . . . H461 H 0.3039 -0.0869 0.6299 0.0350 1.0000 Uiso R . . . . . . H561 H 0.1901 0.0034 0.5984 0.0344 1.0000 Uiso R . . . . . . H861 H 0.1246 0.1465 0.5624 0.0393 1.0000 Uiso R . . . . . . H961 H 0.1313 0.2776 0.5407 0.0418 1.0000 Uiso R . . . . . . H1061 H 0.3351 0.3865 0.5506 0.0419 1.0000 Uiso R . . . . . . H1161 H 0.5448 0.3636 0.5830 0.0399 1.0000 Uiso R . . . . . . H1561 H 0.8166 0.3835 0.6699 0.0309 1.0000 Uiso R . . . . . . H1661 H 1.0831 0.3847 0.6482 0.0328 1.0000 Uiso R . . . . . . H1761 H 1.1155 0.3046 0.6111 0.0317 1.0000 Uiso R . . . . . . H1861 H 0.8828 0.2269 0.5943 0.0280 1.0000 Uiso R . . . . . . H2061 H 0.4119 0.3427 0.7168 0.0407 1.0000 Uiso R . . . . . . H2062 H 0.3253 0.2692 0.6990 0.0407 1.0000 Uiso R . . . . . . H2063 H 0.2992 0.3707 0.6923 0.0407 1.0000 Uiso R . . . . . . H271 H -0.0839 0.0779 0.7782 0.0295 1.0000 Uiso R . . . . . . H371 H 0.1215 0.0540 0.8103 0.0388 1.0000 Uiso R . . . . . . H471 H 0.3270 0.1612 0.8210 0.0451 1.0000 Uiso R . . . . . . H571 H 0.3331 0.2944 0.7994 0.0334 1.0000 Uiso R . . . . . . H871 H 0.2726 0.4389 0.7641 0.0328 1.0000 Uiso R . . . . . . H971 H 0.1590 0.5290 0.7323 0.0385 1.0000 Uiso R . . . . . . H1071 H -0.0761 0.4859 0.7071 0.0347 1.0000 Uiso R . . . . . . H1171 H -0.2132 0.3501 0.7139 0.0271 1.0000 Uiso R . . . . . . H1571 H -0.3567 0.0581 0.6920 0.0288 1.0000 Uiso R . . . . . . H1671 H -0.6238 0.0570 0.7134 0.0321 1.0000 Uiso R . . . . . . H1771 H -0.6580 0.1375 0.7511 0.0318 1.0000 Uiso R . . . . . . H1871 H -0.4191 0.2167 0.7675 0.0285 1.0000 Uiso R . . . . . . H2071 H 0.0495 0.1014 0.6449 0.0447 1.0000 Uiso R . . . . . . H2072 H 0.1613 0.0733 0.6695 0.0447 1.0000 Uiso R . . . . . . H2073 H 0.1332 0.1749 0.6630 0.0447 1.0000 Uiso R . . . . . . H281 H 0.4089 0.4623 0.8382 0.0303 1.0000 Uiso R . . . . . . H381 H 0.6076 0.4888 0.8051 0.0386 1.0000 Uiso R . . . . . . H481 H 0.8200 0.3856 0.7942 0.0412 1.0000 Uiso R . . . . . . H581 H 0.8302 0.2499 0.8148 0.0343 1.0000 Uiso R . . . . . . H881 H 0.7686 0.0997 0.8479 0.0338 1.0000 Uiso R . . . . . . H981 H 0.6518 0.0047 0.8784 0.0341 1.0000 Uiso R . . . . . . H1081 H 0.4203 0.0453 0.9043 0.0344 1.0000 Uiso R . . . . . . H1181 H 0.2914 0.1838 0.9003 0.0293 1.0000 Uiso R . . . . . . H1581 H 0.1253 0.4541 0.9288 0.0323 1.0000 Uiso R . . . . . . H1681 H -0.1330 0.4669 0.9049 0.0379 1.0000 Uiso R . . . . . . H1781 H -0.1537 0.4087 0.8643 0.0362 1.0000 Uiso R . . . . . . H1881 H 0.0894 0.3365 0.8466 0.0346 1.0000 Uiso R . . . . . . H2081 H 0.5268 0.3975 0.9751 0.0567 1.0000 Uiso R . . . . . . H2083 H 0.6402 0.4352 0.9518 0.0567 1.0000 Uiso R . . . . . . H2082 H 0.6151 0.3317 0.9550 0.0567 1.0000 Uiso 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 0.0282(18) 0.0259(15) 0.0224(16) 0.0002(13) 0.0013(13) -0.0013(13) O11 0.0250(14) 0.055(2) 0.0301(16) -0.0089(14) 0.0036(13) 0.0054(15) O21 0.0258(17) 0.0549(19) 0.0225(14) -0.0018(13) -0.0056(12) -0.0002(15) C121 0.023(2) 0.0199(15) 0.027(2) 0.0080(14) -0.0006(15) 0.0049(15) C111 0.022(2) 0.0306(18) 0.033(2) -0.0047(16) -0.0038(18) 0.0023(17) C101 0.028(2) 0.0278(17) 0.030(2) -0.0009(18) -0.0070(16) 0.0048(17) C91 0.030(2) 0.032(2) 0.023(2) 0.0040(16) -0.0100(15) -0.0048(18) C81 0.019(2) 0.0348(18) 0.025(2) 0.0061(16) -0.0032(17) -0.0009(16) C71 0.016(2) 0.0320(16) 0.0196(19) 0.0061(15) -0.0079(14) 0.0017(15) C61 0.024(2) 0.0333(17) 0.0099(18) 0.0067(14) -0.0042(14) 0.0015(15) C51 0.034(3) 0.0405(19) 0.023(2) 0.0054(18) 0.0052(17) 0.006(2) C41 0.039(3) 0.043(2) 0.024(2) -0.0005(17) 0.0062(19) 0.010(2) C31 0.032(2) 0.034(2) 0.024(2) -0.0060(17) -0.0060(16) 0.0070(17) C21 0.031(2) 0.0303(16) 0.024(2) 0.0009(16) -0.0016(17) 0.0016(18) C11 0.021(2) 0.0283(16) 0.018(2) 0.0028(14) -0.0050(15) 0.0043(15) C131 0.0327(19) 0.0114(17) 0.0234(15) -0.0039(16) -0.0003(13) -0.0027(16) C141 0.0211(17) 0.0166(19) 0.0239(14) -0.0055(15) 0.0026(13) 0.0026(15) C151 0.0232(19) 0.024(2) 0.034(2) -0.0003(18) 0.0041(14) 0.0031(17) C161 0.025(2) 0.024(2) 0.0456(18) 0.0011(18) 0.0029(17) -0.0059(18) C171 0.021(2) 0.031(2) 0.0444(18) -0.0046(19) -0.0020(17) 0.0067(17) C181 0.0284(19) 0.029(2) 0.027(2) -0.0078(17) -0.0018(14) 0.0049(17) C191 0.0235(14) 0.022(2) 0.0258(16) 0.0049(16) -0.0043(13) 0.0100(17) C201 0.029(3) 0.066(3) 0.028(2) -0.003(2) -0.0080(18) 0.000(2) N12 0.0227(18) 0.0272(15) 0.0273(18) -0.0041(13) 0.0044(13) 0.0008(13) O12 0.0221(15) 0.064(2) 0.0347(17) -0.0077(16) 0.0047(13) 0.0000(15) O22 0.0238(17) 0.0521(18) 0.0237(12) -0.0041(13) -0.0045(12) -0.0008(15) C12 0.014(2) 0.0304(17) 0.030(2) -0.0001(15) -0.0059(15) 0.0000(15) C22 0.026(2) 0.0375(19) 0.024(2) 0.0010(15) 0.0004(18) 0.0036(17) C32 0.031(2) 0.0324(19) 0.042(2) 0.0036(18) -0.0187(17) 0.0001(18) C42 0.043(3) 0.029(2) 0.038(2) -0.0096(16) -0.0187(18) 0.010(2) C52 0.032(2) 0.036(2) 0.035(2) -0.0128(16) -0.0058(19) 0.0095(17) C62 0.020(2) 0.0278(17) 0.032(2) -0.0086(16) -0.0033(16) -0.0021(16) C72 0.021(2) 0.0304(17) 0.025(2) -0.0078(15) -0.0020(15) -0.0035(15) C82 0.023(2) 0.0405(19) 0.023(2) -0.0101(17) 0.0001(16) -0.0010(18) C92 0.031(2) 0.045(2) 0.020(2) -0.0018(17) 0.0050(18) -0.0086(18) C102 0.031(2) 0.035(2) 0.024(2) -0.0008(17) -0.0033(16) -0.0058(17) C112 0.021(2) 0.0348(17) 0.021(2) -0.0048(16) -0.0062(15) -0.0018(18) C122 0.018(2) 0.0344(17) 0.023(2) -0.0037(15) -0.0009(15) -0.0040(16) C132 0.0149(16) 0.028(2) 0.0267(17) -0.0040(16) 0.0060(12) -0.0050(16) C142 0.0206(16) 0.021(2) 0.0202(16) 0.0056(14) -0.0024(13) -0.0004(15) C152 0.0272(19) 0.024(2) 0.0212(19) -0.0037(16) 0.0007(14) -0.0007(17) C162 0.0166(19) 0.029(2) 0.037(2) 0.0012(17) 0.0064(16) 0.0020(18) C172 0.023(2) 0.031(2) 0.038(2) 0.0013(17) -0.0099(18) 0.0026(18) C182 0.0279(18) 0.033(2) 0.023(2) -0.0055(17) -0.0053(15) -0.0043(18) C192 0.0196(15) 0.029(2) 0.0241(14) 0.0011(17) -0.0034(12) -0.0018(18) C202 0.038(2) 0.049(3) 0.032(2) -0.006(2) -0.0152(18) 0.005(2) N13 0.0201(18) 0.0248(14) 0.0292(18) 0.0002(13) -0.0071(13) -0.0016(13) O13 0.0224(14) 0.0453(19) 0.0305(16) 0.0004(14) 0.0009(14) 0.0059(15) O23 0.0255(17) 0.0289(16) 0.0285(14) 0.0056(12) 0.0049(12) -0.0018(13) C13 0.0107(19) 0.0219(15) 0.0198(19) -0.0060(13) 0.0096(14) 0.0009(14) C23 0.022(2) 0.0296(17) 0.0178(19) -0.0023(15) 0.0044(17) 0.0008(16) C33 0.019(2) 0.0216(16) 0.026(2) -0.0012(16) 0.0061(15) 0.0085(16) C43 0.029(2) 0.0302(19) 0.022(2) 0.0014(16) 0.0041(16) -0.0080(18) C53 0.023(2) 0.0325(18) 0.022(2) -0.0039(16) -0.0080(18) -0.0058(17) C63 0.014(2) 0.0260(15) 0.022(2) -0.0052(14) 0.0053(14) -0.0005(15) C73 0.014(2) 0.0270(17) 0.026(2) -0.0036(15) -0.0002(15) 0.0029(15) C83 0.020(2) 0.0396(19) 0.022(2) -0.0043(17) -0.0001(16) 0.0074(18) C93 0.033(3) 0.046(2) 0.025(2) 0.0076(18) -0.0083(19) 0.0102(19) C103 0.041(3) 0.031(2) 0.027(2) 0.0035(17) -0.0019(18) 0.0066(17) C113 0.030(3) 0.0277(17) 0.031(2) 0.0007(16) -0.0054(18) -0.0025(18) C123 0.018(2) 0.0219(15) 0.022(2) -0.0043(14) -0.0008(15) 0.0036(15) C133 0.0164(18) 0.024(2) 0.0284(15) -0.0033(17) -0.0023(13) -0.0016(15) C143 0.0158(17) 0.020(2) 0.0282(15) -0.0026(17) -0.0034(13) 0.0028(16) C153 0.030(2) 0.021(2) 0.0216(19) -0.0008(17) -0.0102(14) -0.0012(17) C163 0.019(2) 0.0219(19) 0.0409(17) -0.0043(18) -0.0128(17) -0.0056(17) C173 0.015(2) 0.035(2) 0.0386(17) 0.0059(19) 0.0011(17) -0.0042(18) C183 0.0213(19) 0.034(2) 0.026(2) -0.0010(19) -0.0005(14) 0.0003(17) C193 0.0246(15) 0.019(2) 0.0203(17) -0.0083(14) -0.0001(14) 0.0015(17) C203 0.031(2) 0.036(2) 0.030(2) 0.0057(19) 0.0092(18) 0.002(2) N14 0.0179(17) 0.0252(14) 0.0187(16) -0.0005(13) -0.0040(12) 0.0000(13) O14 0.0193(13) 0.0472(19) 0.0334(17) -0.0013(14) -0.0069(14) -0.0009(14) O24 0.0315(18) 0.0396(17) 0.0204(14) 0.0033(12) 0.0012(12) 0.0047(14) C124 0.024(2) 0.0238(15) 0.024(2) -0.0016(15) -0.0012(15) -0.0011(15) C114 0.020(2) 0.0244(16) 0.024(2) -0.0048(14) -0.0024(17) 0.0046(16) C104 0.028(2) 0.0249(17) 0.026(2) 0.0027(17) 0.0076(16) 0.0006(17) C94 0.026(2) 0.032(2) 0.026(2) -0.0086(16) 0.0097(15) -0.0063(18) C84 0.021(2) 0.0402(18) 0.020(2) -0.0085(16) 0.0039(17) -0.0061(17) C74 0.019(2) 0.0304(16) 0.024(2) -0.0075(15) 0.0000(15) 0.0044(15) C64 0.016(2) 0.0343(17) 0.018(2) -0.0054(15) -0.0010(14) 0.0010(16) C54 0.025(2) 0.045(2) 0.023(2) -0.0036(17) -0.0084(17) 0.000(2) C44 0.034(3) 0.040(2) 0.028(2) -0.0032(18) -0.011(2) 0.0115(19) C34 0.037(3) 0.039(2) 0.025(2) 0.0035(18) -0.0078(18) 0.0053(18) C24 0.029(2) 0.0258(16) 0.0137(19) -0.0044(15) -0.0014(16) 0.0041(18) C14 0.017(2) 0.0285(16) 0.020(2) 0.0007(14) -0.0041(14) 0.0024(16) C134 0.0170(17) 0.021(2) 0.0271(15) -0.0023(17) -0.0036(12) 0.0002(15) C144 0.0238(17) 0.0112(19) 0.0273(15) -0.0060(16) 0.0008(13) -0.0010(16) C154 0.028(2) 0.021(2) 0.0273(19) 0.0009(17) -0.0074(14) -0.0003(17) C164 0.023(2) 0.0212(19) 0.0429(17) -0.0021(19) -0.0051(16) -0.0014(18) C174 0.019(2) 0.028(2) 0.0425(17) 0.0073(19) 0.0025(17) -0.0030(17) C184 0.025(2) 0.031(2) 0.030(2) 0.0029(19) 0.0019(14) -0.0023(18) C194 0.0219(14) 0.027(2) 0.0203(17) -0.0033(15) -0.0065(14) -0.0028(17) C204 0.032(2) 0.039(2) 0.024(2) -0.0042(18) 0.0004(17) 0.000(2) N15 0.0285(18) 0.0246(14) 0.0239(17) -0.0043(13) 0.0002(13) -0.0024(13) O15 0.0225(14) 0.055(2) 0.0303(16) 0.0087(14) 0.0014(13) -0.0050(15) O25 0.0255(16) 0.0293(15) 0.0213(13) 0.0021(11) -0.0044(11) 0.0009(12) C15 0.029(3) 0.0296(17) 0.030(2) -0.0039(15) 0.0018(16) 0.0061(16) C25 0.022(2) 0.0297(17) 0.034(2) -0.0015(15) -0.0079(17) 0.0007(16) C35 0.033(3) 0.0310(18) 0.032(2) -0.0056(18) 0.0005(17) 0.0036(18) C45 0.026(2) 0.031(2) 0.036(2) -0.0129(16) -0.0042(16) 0.0051(18) C55 0.022(2) 0.0396(18) 0.025(2) -0.0144(16) -0.0025(17) 0.0043(17) C65 0.025(2) 0.0332(16) 0.023(2) -0.0130(15) -0.0042(15) 0.0003(16) C75 0.026(2) 0.0353(18) 0.023(2) -0.0116(14) -0.0030(15) -0.0071(16) C85 0.036(3) 0.045(2) 0.024(2) -0.0124(17) 0.0041(17) -0.001(2) C95 0.036(3) 0.055(2) 0.027(2) 0.0004(17) 0.005(2) -0.009(2) C105 0.047(3) 0.033(2) 0.029(2) -0.0005(18) -0.0010(18) -0.0086(18) C115 0.034(3) 0.0311(18) 0.028(2) -0.0015(16) -0.0051(17) -0.0053(19) C125 0.033(2) 0.0301(17) 0.019(2) -0.0054(14) -0.0018(15) -0.0042(16) C135 0.029(2) 0.026(2) 0.0259(16) -0.0002(17) 0.0005(13) 0.0002(16) C145 0.0221(17) 0.0147(19) 0.0259(15) 0.0001(15) 0.0007(13) 0.0004(15) C155 0.0243(19) 0.022(2) 0.030(2) 0.0037(17) 0.0037(14) 0.0014(17) C165 0.021(2) 0.029(2) 0.0420(18) -0.0022(18) 0.0034(17) 0.0081(18) C175 0.028(2) 0.033(2) 0.0393(18) 0.0049(19) -0.0032(18) 0.0004(18) C185 0.035(2) 0.032(2) 0.025(2) 0.0021(18) -0.0027(15) 0.0006(19) C195 0.0231(14) 0.0202(19) 0.0210(15) -0.0037(15) 0.0005(13) -0.0018(17) C205 0.028(2) 0.035(2) 0.034(2) 0.0095(18) -0.0111(18) -0.009(2) N16 0.0163(17) 0.0262(15) 0.0173(16) -0.0054(12) 0.0016(12) -0.0034(13) O16 0.0189(15) 0.060(2) 0.0328(16) -0.0156(15) 0.0034(13) -0.0086(16) O26 0.0220(16) 0.0411(17) 0.0207(12) -0.0049(13) 0.0013(11) -0.0006(14) C16 0.023(2) 0.0205(16) 0.0214(19) -0.0090(13) -0.0032(15) -0.0019(15) C26 0.023(2) 0.032(2) 0.024(2) 0.0007(15) 0.0013(17) -0.0050(16) C36 0.038(2) 0.0265(18) 0.032(2) 0.0024(17) 0.0019(17) -0.0033(17) C46 0.025(2) 0.024(2) 0.038(2) -0.0108(15) 0.0132(16) -0.0015(17) C56 0.026(2) 0.0321(19) 0.028(2) -0.0160(15) 0.0040(17) -0.0074(17) C66 0.0090(18) 0.0286(17) 0.0202(19) -0.0117(14) 0.0052(14) 0.0010(14) C76 0.013(2) 0.0378(19) 0.021(2) -0.0066(15) 0.0025(14) 0.0027(15) C86 0.022(2) 0.049(2) 0.028(2) -0.0023(17) -0.0054(16) -0.003(2) C96 0.029(3) 0.045(2) 0.030(2) -0.0060(17) -0.004(2) 0.0084(18) C106 0.037(3) 0.040(2) 0.028(2) 0.0073(19) -0.0017(18) 0.0028(18) C116 0.039(3) 0.0315(19) 0.030(2) -0.0011(16) -0.0074(18) -0.006(2) C126 0.0098(19) 0.0383(18) 0.0136(18) 0.0010(14) 0.0091(13) -0.0007(15) C136 0.0173(16) 0.0166(19) 0.0257(18) -0.0018(15) -0.0019(13) -0.0025(15) C146 0.0169(16) 0.0166(19) 0.0238(18) -0.0002(14) -0.0051(13) 0.0052(15) C156 0.0244(18) 0.021(2) 0.032(2) -0.0099(17) -0.0060(15) 0.0038(16) C166 0.0185(19) 0.025(2) 0.039(2) -0.0031(16) -0.0080(17) 0.0015(17) C176 0.0102(19) 0.038(2) 0.031(2) 0.0011(16) -0.0023(16) 0.0049(16) C186 0.0202(17) 0.026(2) 0.024(2) -0.0017(16) 0.0023(14) -0.0005(16) C196 0.0226(15) 0.0174(18) 0.0221(15) -0.0019(16) -0.0018(13) 0.0015(17) C206 0.022(2) 0.049(3) 0.032(2) -0.010(2) 0.0047(17) 0.002(2) N17 0.0170(17) 0.0244(15) 0.0199(16) -0.0005(12) -0.0022(12) 0.0001(12) O17 0.0174(14) 0.057(2) 0.0310(17) -0.0099(15) -0.0016(13) -0.0005(15) O27 0.0242(16) 0.0461(17) 0.0182(12) -0.0008(13) 0.0023(12) -0.0081(15) C17 0.0084(18) 0.0266(16) 0.0210(18) -0.0063(13) -0.0008(13) 0.0031(14) C27 0.024(2) 0.0291(17) 0.021(2) -0.0035(15) 0.0038(15) 0.0048(18) C37 0.036(3) 0.036(2) 0.025(2) 0.0022(18) -0.0014(17) 0.0084(17) C47 0.034(3) 0.051(2) 0.027(2) -0.0006(18) -0.005(2) 0.0043(19) C57 0.026(2) 0.040(2) 0.0173(19) -0.0135(15) -0.0050(15) -0.0033(19) C67 0.018(2) 0.0310(19) 0.022(2) -0.0058(15) -0.0011(15) -0.0039(15) C77 0.018(2) 0.0308(18) 0.0185(19) -0.0069(14) 0.0040(15) -0.0035(15) C87 0.014(2) 0.033(2) 0.037(2) -0.0119(16) 0.0076(17) -0.0054(16) C97 0.034(2) 0.031(2) 0.032(2) -0.0053(16) 0.0121(17) -0.0121(19) C107 0.027(2) 0.0280(18) 0.032(2) 0.0018(17) 0.0084(17) -0.0004(17) C117 0.018(2) 0.0239(19) 0.025(2) 0.0011(15) 0.0054(16) 0.0036(15) C127 0.0134(19) 0.0276(17) 0.0155(18) -0.0026(13) 0.0065(14) -0.0021(15) C137 0.0204(16) 0.0179(19) 0.0184(17) 0.0042(14) -0.0045(13) 0.0012(15) C147 0.0174(16) 0.025(2) 0.0190(17) 0.0012(14) -0.0015(13) 0.0005(16) C157 0.0227(18) 0.029(2) 0.020(2) 0.0015(16) -0.0085(14) 0.0000(17) C167 0.021(2) 0.027(2) 0.032(2) 0.0002(16) -0.0037(17) -0.0077(18) C177 0.0213(19) 0.022(2) 0.036(2) 0.0013(15) 0.0014(18) -0.0022(17) C187 0.0218(16) 0.020(2) 0.029(2) 0.0001(16) 0.0008(15) -0.0013(16) C197 0.0155(14) 0.029(2) 0.0223(15) -0.0020(17) -0.0025(12) 0.0109(18) C207 0.034(3) 0.046(3) 0.031(2) 0.003(2) 0.0141(19) 0.002(2) N18 0.0240(18) 0.0291(16) 0.0216(17) 0.0013(13) -0.0018(12) 0.0085(13) O18 0.0265(15) 0.059(2) 0.0253(15) -0.0060(15) -0.0047(12) 0.0027(15) O28 0.0313(17) 0.0454(17) 0.0212(12) -0.0094(13) -0.0021(11) 0.0044(15) C18 0.023(2) 0.0298(17) 0.0155(18) -0.0026(13) -0.0061(14) 0.0028(15) C28 0.024(2) 0.0297(18) 0.022(2) -0.0001(15) -0.0027(15) 0.0014(17) C38 0.035(2) 0.037(2) 0.025(2) 0.0062(18) 0.0021(16) -0.0018(17) C48 0.028(2) 0.045(2) 0.030(2) -0.0038(17) 0.0093(19) -0.0067(18) C58 0.022(2) 0.039(2) 0.025(2) -0.0100(16) -0.0027(15) -0.0032(19) C68 0.019(2) 0.0328(18) 0.0221(19) -0.0026(15) -0.0057(14) 0.0035(15) C78 0.021(2) 0.0287(17) 0.022(2) -0.0056(14) -0.0080(15) 0.0040(15) C88 0.028(2) 0.0342(19) 0.022(2) -0.0087(16) -0.0032(16) 0.0105(17) C98 0.030(2) 0.028(2) 0.029(2) -0.0033(15) -0.0075(16) 0.0141(17) C108 0.032(2) 0.0268(17) 0.027(2) -0.0002(16) -0.0015(17) 0.0048(17) C118 0.034(2) 0.0235(17) 0.0155(19) -0.0079(14) -0.0014(16) 0.0048(16) C128 0.0155(19) 0.0270(16) 0.0217(19) -0.0019(14) -0.0094(14) 0.0006(14) C138 0.0203(17) 0.0206(19) 0.0241(16) 0.0064(15) 0.0036(13) 0.0015(15) C148 0.0237(17) 0.0120(18) 0.0258(16) 0.0049(14) 0.0026(13) 0.0001(15) C158 0.0283(19) 0.025(2) 0.029(2) 0.0007(17) 0.0040(14) 0.0029(17) C168 0.020(2) 0.034(2) 0.041(2) -0.0027(17) 0.0063(16) 0.0047(19) C178 0.0165(19) 0.036(2) 0.0380(19) 0.0037(17) -0.0060(17) -0.0003(17) C188 0.0258(19) 0.030(2) 0.030(2) -0.0023(17) -0.0037(15) -0.0013(18) C198 0.0316(16) 0.0203(19) 0.0200(14) 0.0006(17) -0.0008(12) 0.0008(18) C208 0.045(3) 0.068(3) 0.030(2) -0.012(2) -0.015(2) 0.007(3) _refine_ls_extinction_method None #_oxford_refine_ls_scale 0.9170(4) #loop_ # _oxford_twin_element_scale_factors # 0.4611(6) # 0.5389(6) 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 N11 . C121 . 1.395(4) yes N11 . C11 . 1.414(5) yes N11 . C131 . 1.410(5) yes O11 . C191 . 1.200(5) yes O21 . C191 . 1.358(5) yes O21 . C201 . 1.460(6) yes C121 . C111 . 1.390(4) yes C121 . C71 . 1.412(5) yes C111 . C101 . 1.379(4) yes C111 . H1111 . 0.950 no C101 . C91 . 1.387(4) yes C101 . H1011 . 0.950 no C91 . C81 . 1.374(4) yes C91 . H911 . 0.950 no C81 . C71 . 1.386(5) yes C81 . H811 . 0.950 no C71 . C61 . 1.456(5) yes C61 . C51 . 1.393(6) yes C61 . C11 . 1.389(6) yes C51 . C41 . 1.373(6) yes C51 . H511 . 0.950 no C41 . C31 . 1.398(7) yes C41 . H411 . 0.950 no C31 . C21 . 1.378(6) yes C31 . H311 . 0.950 no C21 . C11 . 1.385(5) yes C21 . H211 . 0.950 no C131 . C141 . 1.406(6) yes C131 . C181 . 1.382(6) yes C141 . C151 . 1.385(6) yes C141 . C191 . 1.490(6) yes C151 . C161 . 1.372(6) yes C151 . H1511 . 0.950 no C161 . C171 . 1.388(6) yes C161 . H1611 . 0.950 no C171 . C181 . 1.390(6) yes C171 . H1711 . 0.950 no C181 . H1811 . 0.950 no C201 . H2011 . 0.980 no C201 . H2012 . 0.980 no C201 . H2013 . 0.980 no N12 . C12 . 1.387(4) yes N12 . C122 . 1.377(5) yes N12 . C132 . 1.445(5) yes O12 . C192 . 1.213(5) yes O22 . C192 . 1.339(5) yes O22 . C202 . 1.443(5) yes C12 . C22 . 1.382(4) yes C12 . C62 . 1.415(5) yes C22 . C32 . 1.373(4) yes C22 . H221 . 0.950 no C32 . C42 . 1.397(4) yes C32 . H321 . 0.950 no C42 . C52 . 1.382(5) yes C42 . H421 . 0.950 no C52 . C62 . 1.385(5) yes C52 . H521 . 0.950 no C62 . C72 . 1.436(5) yes C72 . C82 . 1.416(6) yes C72 . C122 . 1.422(6) yes C82 . C92 . 1.375(6) yes C82 . H821 . 0.950 no C92 . C102 . 1.418(6) yes C92 . H921 . 0.950 no C102 . C112 . 1.377(6) yes C102 . H1021 . 0.950 no C112 . C122 . 1.381(5) yes C112 . H1121 . 0.950 no C132 . C142 . 1.387(6) yes C132 . C182 . 1.387(6) yes C142 . C152 . 1.394(6) yes C142 . C192 . 1.484(6) yes C152 . C162 . 1.393(6) yes C152 . H1521 . 0.950 no C162 . C172 . 1.387(6) yes C162 . H1621 . 0.950 no C172 . C182 . 1.383(6) yes C172 . H1721 . 0.950 no C182 . H1821 . 0.950 no C202 . H2021 . 0.980 no C202 . H2022 . 0.980 no C202 . H2023 . 0.980 no N13 . C13 . 1.390(4) yes N13 . C123 . 1.406(5) yes N13 . C133 . 1.430(5) yes O13 . C193 . 1.194(5) yes O23 . C193 . 1.346(5) yes O23 . C203 . 1.433(5) yes C13 . C23 . 1.378(4) yes C13 . C63 . 1.405(4) yes C23 . C33 . 1.372(4) yes C23 . H231 . 0.950 no C33 . C43 . 1.397(4) yes C33 . H331 . 0.950 no C43 . C53 . 1.367(4) yes C43 . H431 . 0.950 no C53 . C63 . 1.404(5) yes C53 . H531 . 0.950 no C63 . C73 . 1.453(5) yes C73 . C83 . 1.398(6) yes C73 . C123 . 1.417(6) yes C83 . C93 . 1.361(6) yes C83 . H831 . 0.950 no C93 . C103 . 1.411(7) yes C93 . H931 . 0.950 no C103 . C113 . 1.362(6) yes C103 . H1031 . 0.950 no C113 . C123 . 1.371(5) yes C113 . H1131 . 0.950 no C133 . C143 . 1.390(6) yes C133 . C183 . 1.381(6) yes C143 . C153 . 1.400(6) yes C143 . C193 . 1.481(6) yes C153 . C163 . 1.376(6) yes C153 . H1531 . 0.950 no C163 . C173 . 1.401(6) yes C163 . H1631 . 0.950 no C173 . C183 . 1.370(6) yes C173 . H1731 . 0.950 no C183 . H1831 . 0.950 no C203 . H2031 . 0.980 no C203 . H2032 . 0.980 no C203 . H2033 . 0.980 no N14 . C124 . 1.391(4) yes N14 . C14 . 1.391(5) yes N14 . C134 . 1.431(5) yes O14 . C194 . 1.196(5) yes O24 . C194 . 1.339(5) yes O24 . C204 . 1.439(6) yes C124 . C114 . 1.388(4) yes C124 . C74 . 1.410(5) yes C114 . C104 . 1.378(4) yes C114 . H1141 . 0.950 no C104 . C94 . 1.391(4) yes C104 . H1041 . 0.950 no C94 . C84 . 1.371(4) yes C94 . H941 . 0.950 no C84 . C74 . 1.390(5) yes C84 . H841 . 0.950 no C74 . C64 . 1.430(5) yes C64 . C54 . 1.392(6) yes C64 . C14 . 1.422(6) yes C54 . C44 . 1.369(6) yes C54 . H541 . 0.950 no C44 . C34 . 1.385(7) yes C44 . H441 . 0.950 no C34 . C24 . 1.398(6) yes C34 . H341 . 0.950 no C24 . C14 . 1.374(5) yes C24 . H241 . 0.950 no C134 . C144 . 1.387(6) yes C134 . C184 . 1.402(6) yes C144 . C154 . 1.388(6) yes C144 . C194 . 1.498(6) yes C154 . C164 . 1.381(6) yes C154 . H1541 . 0.950 no C164 . C174 . 1.359(6) yes C164 . H1641 . 0.950 no C174 . C184 . 1.371(6) yes C174 . H1741 . 0.950 no C184 . H1841 . 0.950 no C204 . H2041 . 0.980 no C204 . H2042 . 0.980 no C204 . H2043 . 0.980 no N15 . C15 . 1.388(4) yes N15 . C125 . 1.400(5) yes N15 . C135 . 1.439(6) yes O15 . C195 . 1.209(5) yes O25 . C195 . 1.345(5) yes O25 . C205 . 1.474(5) yes C15 . C25 . 1.387(4) yes C15 . C65 . 1.405(5) yes C25 . C35 . 1.369(4) yes C25 . H251 . 0.950 no C35 . C45 . 1.393(4) yes C35 . H351 . 0.950 no C45 . C55 . 1.364(5) yes C45 . H451 . 0.950 no C55 . C65 . 1.392(5) yes C55 . H551 . 0.950 no C65 . C75 . 1.451(5) yes C75 . C85 . 1.396(6) yes C75 . C125 . 1.378(6) yes C85 . C95 . 1.371(6) yes C85 . H851 . 0.950 no C95 . C105 . 1.395(7) yes C95 . H951 . 0.950 no C105 . C115 . 1.388(6) yes C105 . H1051 . 0.950 no C115 . C125 . 1.416(6) yes C115 . H1151 . 0.950 no C135 . C145 . 1.382(6) yes C135 . C185 . 1.386(6) yes C145 . C155 . 1.399(6) yes C145 . C195 . 1.491(6) yes C155 . C165 . 1.394(6) yes C155 . H1551 . 0.950 no C165 . C175 . 1.358(6) yes C165 . H1651 . 0.950 no C175 . C185 . 1.379(7) yes C175 . H1751 . 0.950 no C185 . H1851 . 0.950 no C205 . H2051 . 0.980 no C205 . H2052 . 0.980 no C205 . H2053 . 0.980 no N16 . C16 . 1.382(4) yes N16 . C126 . 1.394(5) yes N16 . C136 . 1.426(5) yes O16 . C196 . 1.197(5) yes O26 . C196 . 1.348(5) yes O26 . C206 . 1.439(5) yes C16 . C26 . 1.382(4) yes C16 . C66 . 1.416(4) yes C26 . C36 . 1.361(4) yes C26 . H261 . 0.950 no C36 . C46 . 1.398(4) yes C36 . H361 . 0.950 no C46 . C56 . 1.367(4) yes C46 . H461 . 0.950 no C56 . C66 . 1.388(5) yes C56 . H561 . 0.950 no C66 . C76 . 1.462(5) yes C76 . C86 . 1.405(6) yes C76 . C126 . 1.401(6) yes C86 . C96 . 1.351(6) yes C86 . H861 . 0.950 no C96 . C106 . 1.402(6) yes C96 . H961 . 0.950 no C106 . C116 . 1.390(6) yes C106 . H1061 . 0.950 no C116 . C126 . 1.378(5) yes C116 . H1161 . 0.950 no C136 . C146 . 1.400(6) yes C136 . C186 . 1.384(6) yes C146 . C156 . 1.393(6) yes C146 . C196 . 1.481(6) yes C156 . C166 . 1.379(6) yes C156 . H1561 . 0.950 no C166 . C176 . 1.363(6) yes C166 . H1661 . 0.950 no C176 . C186 . 1.366(6) yes C176 . H1761 . 0.950 no C186 . H1861 . 0.950 no C206 . H2061 . 0.980 no C206 . H2062 . 0.980 no C206 . H2063 . 0.980 no N17 . C17 . 1.383(4) yes N17 . C127 . 1.374(5) yes N17 . C137 . 1.437(5) yes O17 . C197 . 1.195(5) yes O27 . C197 . 1.332(5) yes O27 . C207 . 1.450(5) yes C17 . C27 . 1.383(4) yes C17 . C67 . 1.426(4) yes C27 . C37 . 1.370(4) yes C27 . H271 . 0.950 no C37 . C47 . 1.397(4) yes C37 . H371 . 0.950 no C47 . C57 . 1.377(4) yes C47 . H471 . 0.950 no C57 . C67 . 1.377(5) yes C57 . H571 . 0.950 no C67 . C77 . 1.446(5) yes C77 . C87 . 1.403(6) yes C77 . C127 . 1.423(6) yes C87 . C97 . 1.380(6) yes C87 . H871 . 0.950 no C97 . C107 . 1.389(6) yes C97 . H971 . 0.950 no C107 . C117 . 1.386(5) yes C107 . H1071 . 0.950 no C117 . C127 . 1.386(5) yes C117 . H1171 . 0.950 no C137 . C147 . 1.384(5) yes C137 . C187 . 1.371(6) yes C147 . C157 . 1.398(6) yes C147 . C197 . 1.493(6) yes C157 . C167 . 1.380(6) yes C157 . H1571 . 0.950 no C167 . C177 . 1.383(6) yes C167 . H1671 . 0.950 no C177 . C187 . 1.393(6) yes C177 . H1771 . 0.950 no C187 . H1871 . 0.950 no C207 . H2071 . 0.980 no C207 . H2072 . 0.980 no C207 . H2073 . 0.980 no N18 . C18 . 1.384(4) yes N18 . C128 . 1.375(5) yes N18 . C138 . 1.438(5) yes O18 . C198 . 1.215(5) yes O28 . C198 . 1.325(4) yes O28 . C208 . 1.443(6) yes C18 . C28 . 1.381(4) yes C18 . C68 . 1.403(4) yes C28 . C38 . 1.380(4) yes C28 . H281 . 0.950 no C38 . C48 . 1.394(4) yes C38 . H381 . 0.950 no C48 . C58 . 1.383(4) yes C48 . H481 . 0.950 no C58 . C68 . 1.409(5) yes C58 . H581 . 0.950 no C68 . C78 . 1.439(5) yes C78 . C88 . 1.414(6) yes C78 . C128 . 1.395(6) yes C88 . C98 . 1.382(6) yes C88 . H881 . 0.950 no C98 . C108 . 1.380(6) yes C98 . H981 . 0.950 no C108 . C118 . 1.382(5) yes C108 . H1081 . 0.950 no C118 . C128 . 1.390(6) yes C118 . H1181 . 0.950 no C138 . C148 . 1.394(5) yes C138 . C188 . 1.382(6) yes C148 . C158 . 1.402(6) yes C148 . C198 . 1.492(6) yes C158 . C168 . 1.396(6) yes C158 . H1581 . 0.950 no C168 . C178 . 1.363(6) yes C168 . H1681 . 0.950 no C178 . C188 . 1.393(6) yes C178 . H1781 . 0.950 no C188 . H1881 . 0.950 no C208 . H2081 . 0.980 no C208 . H2083 . 0.980 no C208 . H2082 . 0.980 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 C121 . N11 . C11 . 107.6(3) yes C121 . N11 . C131 . 127.1(2) yes C11 . N11 . C131 . 125.2(3) yes C191 . O21 . C201 . 114.1(4) yes N11 . C121 . C111 . 129.96(8) yes N11 . C121 . C71 . 108.89(19) yes C111 . C121 . C71 . 121.13(19) yes C121 . C111 . C101 . 117.95(8) yes C121 . C111 . H1111 . 121.0 no C101 . C111 . H1111 . 121.1 no C111 . C101 . C91 . 121.47(8) yes C111 . C101 . H1011 . 119.2 no C91 . C101 . H1011 . 119.3 no C101 . C91 . C81 . 120.60(8) yes C101 . C91 . H911 . 119.7 no C81 . C91 . H911 . 119.7 no C91 . C81 . C71 . 119.7(2) yes C91 . C81 . H811 . 120.2 no C71 . C81 . H811 . 120.1 no C121 . C71 . C81 . 119.16(8) yes C121 . C71 . C61 . 107.1(3) yes C81 . C71 . C61 . 133.7(3) yes C71 . C61 . C51 . 134.0(4) yes C71 . C61 . C11 . 106.6(4) yes C51 . C61 . C11 . 119.4(4) yes C61 . C51 . C41 . 118.8(4) yes C61 . C51 . H511 . 120.5 no C41 . C51 . H511 . 120.7 no C51 . C41 . C31 . 120.9(4) yes C51 . C41 . H411 . 119.4 no C31 . C41 . H411 . 119.6 no C41 . C31 . C21 . 121.2(4) yes C41 . C31 . H311 . 119.4 no C21 . C31 . H311 . 119.5 no C31 . C21 . C11 . 117.2(4) yes C31 . C21 . H211 . 121.3 no C11 . C21 . H211 . 121.4 no N11 . C11 . C61 . 109.8(3) yes N11 . C11 . C21 . 127.7(4) yes C61 . C11 . C21 . 122.5(4) yes N11 . C131 . C141 . 121.7(4) yes N11 . C131 . C181 . 118.6(4) yes C141 . C131 . C181 . 119.7(4) yes C131 . C141 . C151 . 119.0(4) yes C131 . C141 . C191 . 120.8(4) yes C151 . C141 . C191 . 120.2(4) yes C141 . C151 . C161 . 120.8(4) yes C141 . C151 . H1511 . 119.6 no C161 . C151 . H1511 . 119.6 no C151 . C161 . C171 . 120.8(4) yes C151 . C161 . H1611 . 119.5 no C171 . C161 . H1611 . 119.6 no C161 . C171 . C181 . 118.8(4) yes C161 . C171 . H1711 . 120.6 no C181 . C171 . H1711 . 120.7 no C171 . C181 . C131 . 120.9(4) yes C171 . C181 . H1811 . 119.5 no C131 . C181 . H1811 . 119.5 no C141 . C191 . O21 . 110.1(4) yes C141 . C191 . O11 . 126.9(4) yes O21 . C191 . O11 . 123.1(4) yes O21 . C201 . H2011 . 109.4 no O21 . C201 . H2012 . 109.5 no H2011 . C201 . H2012 . 109.5 no O21 . C201 . H2013 . 109.5 no H2011 . C201 . H2013 . 109.5 no H2012 . C201 . H2013 . 109.5 no C12 . N12 . C122 . 109.6(3) yes C12 . N12 . C132 . 126.0(2) yes C122 . N12 . C132 . 124.3(3) yes C192 . O22 . C202 . 115.6(4) yes N12 . C12 . C22 . 129.97(8) yes N12 . C12 . C62 . 108.3(2) yes C22 . C12 . C62 . 121.69(19) yes C12 . C22 . C32 . 117.92(8) yes C12 . C22 . H221 . 121.0 no C32 . C22 . H221 . 121.1 no C22 . C32 . C42 . 121.43(8) yes C22 . C32 . H321 . 119.3 no C42 . C32 . H321 . 119.3 no C32 . C42 . C52 . 120.61(8) yes C32 . C42 . H421 . 119.7 no C52 . C42 . H421 . 119.7 no C42 . C52 . C62 . 119.2(2) yes C42 . C52 . H521 . 120.5 no C62 . C52 . H521 . 120.4 no C12 . C62 . C52 . 119.17(8) yes C12 . C62 . C72 . 106.9(3) yes C52 . C62 . C72 . 134.0(3) yes C62 . C72 . C82 . 134.9(4) yes C62 . C72 . C122 . 106.8(4) yes C82 . C72 . C122 . 118.3(4) yes C72 . C82 . C92 . 119.2(4) yes C72 . C82 . H821 . 120.4 no C92 . C82 . H821 . 120.4 no C82 . C92 . C102 . 121.0(4) yes C82 . C92 . H921 . 119.6 no C102 . C92 . H921 . 119.5 no C92 . C102 . C112 . 120.9(4) yes C92 . C102 . H1021 . 119.6 no C112 . C102 . H1021 . 119.5 no C102 . C112 . C122 . 118.4(4) yes C102 . C112 . H1121 . 120.8 no C122 . C112 . H1121 . 120.8 no C72 . C122 . C112 . 122.2(4) yes C72 . C122 . N12 . 108.3(3) yes C112 . C122 . N12 . 129.4(4) yes N12 . C132 . C142 . 122.4(4) yes N12 . C132 . C182 . 116.8(4) yes C142 . C132 . C182 . 120.7(4) yes C132 . C142 . C152 . 118.0(4) yes C132 . C142 . C192 . 122.1(4) yes C152 . C142 . C192 . 119.9(4) yes C142 . C152 . C162 . 121.6(4) yes C142 . C152 . H1521 . 119.2 no C162 . C152 . H1521 . 119.2 no C152 . C162 . C172 . 119.5(4) yes C152 . C162 . H1621 . 120.3 no C172 . C162 . H1621 . 120.2 no C162 . C172 . C182 . 119.3(4) yes C162 . C172 . H1721 . 120.3 no C182 . C172 . H1721 . 120.4 no C132 . C182 . C172 . 120.9(4) yes C132 . C182 . H1821 . 119.5 no C172 . C182 . H1821 . 119.6 no C142 . C192 . O22 . 112.2(4) yes C142 . C192 . O12 . 124.2(4) yes O22 . C192 . O12 . 123.6(4) yes O22 . C202 . H2021 . 109.5 no O22 . C202 . H2022 . 109.6 no H2021 . C202 . H2022 . 109.5 no O22 . C202 . H2023 . 109.3 no H2021 . C202 . H2023 . 109.5 no H2022 . C202 . H2023 . 109.5 no C13 . N13 . C123 . 109.5(2) yes C13 . N13 . C133 . 126.7(2) yes C123 . N13 . C133 . 123.9(3) yes C193 . O23 . C203 . 117.2(4) yes N13 . C13 . C23 . 129.87(8) yes N13 . C13 . C63 . 108.49(19) yes C23 . C13 . C63 . 121.56(18) yes C13 . C23 . C33 . 118.09(8) yes C13 . C23 . H231 . 121.0 no C33 . C23 . H231 . 120.9 no C23 . C33 . C43 . 121.53(8) yes C23 . C33 . H331 . 119.2 no C43 . C33 . H331 . 119.2 no C33 . C43 . C53 . 120.65(8) yes C33 . C43 . H431 . 119.7 no C53 . C43 . H431 . 119.6 no C43 . C53 . C63 . 118.96(19) yes C43 . C53 . H531 . 120.5 no C63 . C53 . H531 . 120.5 no C13 . C63 . C53 . 119.20(8) yes C13 . C63 . C73 . 107.4(3) yes C53 . C63 . C73 . 133.3(3) yes C63 . C73 . C83 . 133.9(4) yes C63 . C73 . C123 . 106.8(4) yes C83 . C73 . C123 . 119.2(4) yes C73 . C83 . C93 . 119.1(4) yes C73 . C83 . H831 . 120.5 no C93 . C83 . H831 . 120.4 no C83 . C93 . C103 . 120.4(4) yes C83 . C93 . H931 . 119.8 no C103 . C93 . H931 . 119.8 no C93 . C103 . C113 . 121.5(4) yes C93 . C103 . H1031 . 119.2 no C113 . C103 . H1031 . 119.3 no C103 . C113 . C123 . 118.5(4) yes C103 . C113 . H1131 . 120.8 no C123 . C113 . H1131 . 120.7 no C73 . C123 . N13 . 107.8(3) yes C73 . C123 . C113 . 121.3(4) yes N13 . C123 . C113 . 130.9(4) yes N13 . C133 . C143 . 120.8(4) yes N13 . C133 . C183 . 118.8(4) yes C143 . C133 . C183 . 120.4(4) yes C133 . C143 . C153 . 117.9(4) yes C133 . C143 . C193 . 122.8(4) yes C153 . C143 . C193 . 119.2(4) yes C143 . C153 . C163 . 121.5(4) yes C143 . C153 . H1531 . 119.3 no C163 . C153 . H1531 . 119.2 no C153 . C163 . C173 . 119.7(4) yes C153 . C163 . H1631 . 120.2 no C173 . C163 . H1631 . 120.1 no C163 . C173 . C183 . 118.9(4) yes C163 . C173 . H1731 . 120.6 no C183 . C173 . H1731 . 120.5 no C133 . C183 . C173 . 121.6(4) yes C133 . C183 . H1831 . 119.2 no C173 . C183 . H1831 . 119.2 no C143 . C193 . O23 . 111.8(4) yes C143 . C193 . O13 . 125.6(4) yes O23 . C193 . O13 . 122.6(4) yes O23 . C203 . H2031 . 109.7 no O23 . C203 . H2032 . 109.4 no H2031 . C203 . H2032 . 109.5 no O23 . C203 . H2033 . 109.4 no H2031 . C203 . H2033 . 109.5 no H2032 . C203 . H2033 . 109.5 no C124 . N14 . C14 . 109.0(2) yes C124 . N14 . C134 . 126.0(2) yes C14 . N14 . C134 . 125.0(3) yes C194 . O24 . C204 . 116.1(4) yes N14 . C124 . C114 . 129.96(8) yes N14 . C124 . C74 . 108.78(19) yes C114 . C124 . C74 . 121.22(18) yes C124 . C114 . C104 . 117.96(8) yes C124 . C114 . H1141 . 121.0 no C104 . C114 . H1141 . 121.1 no C114 . C104 . C94 . 121.45(8) yes C114 . C104 . H1041 . 119.2 no C94 . C104 . H1041 . 119.3 no C104 . C94 . C84 . 120.60(8) yes C104 . C94 . H941 . 119.7 no C84 . C94 . H941 . 119.7 no C94 . C84 . C74 . 119.5(2) yes C94 . C84 . H841 . 120.3 no C74 . C84 . H841 . 120.2 no C124 . C74 . C84 . 119.21(8) yes C124 . C74 . C64 . 107.0(3) yes C84 . C74 . C64 . 133.8(3) yes C74 . C64 . C54 . 134.5(4) yes C74 . C64 . C14 . 107.3(4) yes C54 . C64 . C14 . 118.1(4) yes C64 . C54 . C44 . 119.3(4) yes C64 . C54 . H541 . 120.3 no C44 . C54 . H541 . 120.4 no C54 . C44 . C34 . 122.5(4) yes C54 . C44 . H441 . 118.8 no C34 . C44 . H441 . 118.6 no C44 . C34 . C24 . 119.4(4) yes C44 . C34 . H341 . 120.4 no C24 . C34 . H341 . 120.2 no C34 . C24 . C14 . 118.5(4) yes C34 . C24 . H241 . 120.7 no C14 . C24 . H241 . 120.8 no C64 . C14 . N14 . 107.9(3) yes C64 . C14 . C24 . 122.1(4) yes N14 . C14 . C24 . 130.0(4) yes N14 . C134 . C144 . 122.9(4) yes N14 . C134 . C184 . 117.8(4) yes C144 . C134 . C184 . 119.3(4) yes C134 . C144 . C154 . 119.4(4) yes C134 . C144 . C194 . 121.0(4) yes C154 . C144 . C194 . 119.5(4) yes C144 . C154 . C164 . 120.4(4) yes C144 . C154 . H1541 . 119.8 no C164 . C154 . H1541 . 119.8 no C154 . C164 . C174 . 120.0(4) yes C154 . C164 . H1641 . 120.1 no C174 . C164 . H1641 . 119.9 no C164 . C174 . C184 . 121.0(4) yes C164 . C174 . H1741 . 119.6 no C184 . C174 . H1741 . 119.4 no C134 . C184 . C174 . 119.8(4) yes C134 . C184 . H1841 . 120.0 no C174 . C184 . H1841 . 120.1 no C144 . C194 . O24 . 110.5(4) yes C144 . C194 . O14 . 126.1(4) yes O24 . C194 . O14 . 123.4(4) yes O24 . C204 . H2041 . 109.4 no O24 . C204 . H2042 . 109.5 no H2041 . C204 . H2042 . 109.5 no O24 . C204 . H2043 . 109.5 no H2041 . C204 . H2043 . 109.5 no H2042 . C204 . H2043 . 109.5 no C15 . N15 . C125 . 108.1(3) yes C15 . N15 . C135 . 125.9(2) yes C125 . N15 . C135 . 126.0(3) yes C195 . O25 . C205 . 114.9(3) yes N15 . C15 . C25 . 129.91(8) yes N15 . C15 . C65 . 108.7(2) yes C25 . C15 . C65 . 121.24(19) yes C15 . C25 . C35 . 118.00(8) yes C15 . C25 . H251 . 120.9 no C35 . C25 . H251 . 121.1 no C25 . C35 . C45 . 121.49(8) yes C25 . C35 . H351 . 119.2 no C45 . C35 . H351 . 119.3 no C35 . C45 . C55 . 120.63(8) yes C35 . C45 . H451 . 119.7 no C55 . C45 . H451 . 119.7 no C45 . C55 . C65 . 119.4(2) yes C45 . C55 . H551 . 120.3 no C65 . C55 . H551 . 120.3 no C15 . C65 . C55 . 119.19(8) yes C15 . C65 . C75 . 106.8(3) yes C55 . C65 . C75 . 133.9(3) yes C65 . C75 . C85 . 133.9(4) yes C65 . C75 . C125 . 106.9(4) yes C85 . C75 . C125 . 119.2(4) yes C75 . C85 . C95 . 120.1(5) yes C75 . C85 . H851 . 120.0 no C95 . C85 . H851 . 119.9 no C85 . C95 . C105 . 120.0(4) yes C85 . C95 . H951 . 120.1 no C105 . C95 . H951 . 119.9 no C95 . C105 . C115 . 121.9(4) yes C95 . C105 . H1051 . 119.1 no C115 . C105 . H1051 . 119.0 no C105 . C115 . C125 . 116.4(4) yes C105 . C115 . H1151 . 121.8 no C125 . C115 . H1151 . 121.8 no C115 . C125 . N15 . 128.1(4) yes C115 . C125 . C75 . 122.2(4) yes N15 . C125 . C75 . 109.6(3) yes N15 . C135 . C145 . 120.9(4) yes N15 . C135 . C185 . 118.0(4) yes C145 . C135 . C185 . 121.0(4) yes C135 . C145 . C155 . 118.7(4) yes C135 . C145 . C195 . 122.0(4) yes C155 . C145 . C195 . 119.3(4) yes C145 . C155 . C165 . 120.4(4) yes C145 . C155 . H1551 . 119.8 no C165 . C155 . H1551 . 119.8 no C155 . C165 . C175 . 119.2(4) yes C155 . C165 . H1651 . 120.4 no C175 . C165 . H1651 . 120.4 no C165 . C175 . C185 . 121.9(5) yes C165 . C175 . H1751 . 119.0 no C185 . C175 . H1751 . 119.1 no C135 . C185 . C175 . 118.9(4) yes C135 . C185 . H1851 . 120.5 no C175 . C185 . H1851 . 120.6 no C145 . C195 . O25 . 110.8(4) yes C145 . C195 . O15 . 126.0(4) yes O25 . C195 . O15 . 123.2(4) yes O25 . C205 . H2051 . 109.3 no O25 . C205 . H2052 . 109.6 no H2051 . C205 . H2052 . 109.5 no O25 . C205 . H2053 . 109.6 no H2051 . C205 . H2053 . 109.5 no H2052 . C205 . H2053 . 109.5 no C16 . N16 . C126 . 109.2(2) yes C16 . N16 . C136 . 125.6(2) yes C126 . N16 . C136 . 125.0(3) yes C196 . O26 . C206 . 116.5(4) yes N16 . C16 . C26 . 129.77(8) yes N16 . C16 . C66 . 108.99(19) yes C26 . C16 . C66 . 121.24(18) yes C16 . C26 . C36 . 118.12(8) yes C16 . C26 . H261 . 120.9 no C36 . C26 . H261 . 121.0 no C26 . C36 . C46 . 121.57(8) yes C26 . C36 . H361 . 119.2 no C46 . C36 . H361 . 119.3 no C36 . C46 . C56 . 120.71(8) yes C36 . C46 . H461 . 119.6 no C56 . C46 . H461 . 119.6 no C46 . C56 . C66 . 119.18(19) yes C46 . C56 . H561 . 120.4 no C66 . C56 . H561 . 120.4 no C16 . C66 . C56 . 119.14(8) yes C16 . C66 . C76 . 106.0(3) yes C56 . C66 . C76 . 134.9(3) yes C66 . C76 . C86 . 134.0(4) yes C66 . C76 . C126 . 107.1(3) yes C86 . C76 . C126 . 118.9(4) yes C76 . C86 . C96 . 118.4(4) yes C76 . C86 . H861 . 120.8 no C96 . C86 . H861 . 120.8 no C86 . C96 . C106 . 122.3(4) yes C86 . C96 . H961 . 119.0 no C106 . C96 . H961 . 118.7 no C96 . C106 . C116 . 120.5(4) yes C96 . C106 . H1061 . 119.8 no C116 . C106 . H1061 . 119.7 no C106 . C116 . C126 . 116.9(4) yes C106 . C116 . H1161 . 121.5 no C126 . C116 . H1161 . 121.7 no C76 . C126 . N16 . 108.6(3) yes C76 . C126 . C116 . 123.0(4) yes N16 . C126 . C116 . 128.3(4) yes N16 . C136 . C146 . 121.1(4) yes N16 . C136 . C186 . 118.6(4) yes C146 . C136 . C186 . 120.3(4) yes C136 . C146 . C156 . 117.9(4) yes C136 . C146 . C196 . 121.7(4) yes C156 . C146 . C196 . 120.4(4) yes C146 . C156 . C166 . 121.1(4) yes C146 . C156 . H1561 . 119.5 no C166 . C156 . H1561 . 119.5 no C156 . C166 . C176 . 119.6(4) yes C156 . C166 . H1661 . 120.2 no C176 . C166 . H1661 . 120.1 no C166 . C176 . C186 . 121.0(4) yes C166 . C176 . H1761 . 119.4 no C186 . C176 . H1761 . 119.5 no C136 . C186 . C176 . 120.0(4) yes C136 . C186 . H1861 . 120.1 no C176 . C186 . H1861 . 119.9 no C146 . C196 . O26 . 111.9(4) yes C146 . C196 . O16 . 126.1(4) yes O26 . C196 . O16 . 122.0(4) yes O26 . C206 . H2061 . 109.4 no O26 . C206 . H2062 . 109.3 no H2061 . C206 . H2062 . 109.5 no O26 . C206 . H2063 . 109.7 no H2061 . C206 . H2063 . 109.5 no H2062 . C206 . H2063 . 109.5 no C17 . N17 . C127 . 109.5(2) yes C17 . N17 . C137 . 124.1(2) yes C127 . N17 . C137 . 126.4(3) yes C197 . O27 . C207 . 115.6(3) yes N17 . C17 . C27 . 129.81(8) yes N17 . C17 . C67 . 108.94(19) yes C27 . C17 . C67 . 121.17(18) yes C17 . C27 . C37 . 118.00(8) yes C17 . C27 . H271 . 121.0 no C37 . C27 . H271 . 121.0 no C27 . C37 . C47 . 121.48(8) yes C27 . C37 . H371 . 119.2 no C47 . C37 . H371 . 119.3 no C37 . C47 . C57 . 120.66(8) yes C37 . C47 . H471 . 119.7 no C57 . C47 . H471 . 119.7 no C47 . C57 . C67 . 119.4(2) yes C47 . C57 . H571 . 120.3 no C67 . C57 . H571 . 120.3 no C17 . C67 . C57 . 119.16(8) yes C17 . C67 . C77 . 105.9(3) yes C57 . C67 . C77 . 134.9(3) yes C67 . C77 . C87 . 134.3(4) yes C67 . C77 . C127 . 106.9(3) yes C87 . C77 . C127 . 118.8(4) yes C77 . C87 . C97 . 118.2(4) yes C77 . C87 . H871 . 120.8 no C97 . C87 . H871 . 121.0 no C87 . C97 . C107 . 122.4(4) yes C87 . C97 . H971 . 118.7 no C107 . C97 . H971 . 118.9 no C97 . C107 . C117 . 120.7(4) yes C97 . C107 . H1071 . 119.6 no C117 . C107 . H1071 . 119.7 no C107 . C117 . C127 . 117.7(4) yes C107 . C117 . H1171 . 121.1 no C127 . C117 . H1171 . 121.2 no C77 . C127 . C117 . 122.2(4) yes C77 . C127 . N17 . 108.8(3) yes C117 . C127 . N17 . 129.1(4) yes N17 . C137 . C147 . 121.2(4) yes N17 . C137 . C187 . 117.4(3) yes C147 . C137 . C187 . 121.4(4) yes C137 . C147 . C157 . 118.1(4) yes C137 . C147 . C197 . 122.5(4) yes C157 . C147 . C197 . 119.4(4) yes C147 . C157 . C167 . 120.9(4) yes C147 . C157 . H1571 . 119.5 no C167 . C157 . H1571 . 119.6 no C157 . C167 . C177 . 120.1(4) yes C157 . C167 . H1671 . 119.9 no C177 . C167 . H1671 . 120.0 no C167 . C177 . C187 . 119.3(4) yes C167 . C177 . H1771 . 120.3 no C187 . C177 . H1771 . 120.4 no C177 . C187 . C137 . 120.2(4) yes C177 . C187 . H1871 . 119.9 no C137 . C187 . H1871 . 119.9 no C147 . C197 . O27 . 112.2(4) yes C147 . C197 . O17 . 124.4(4) yes O27 . C197 . O17 . 123.4(4) yes O27 . C207 . H2071 . 109.6 no O27 . C207 . H2072 . 109.4 no H2071 . C207 . H2072 . 109.5 no O27 . C207 . H2073 . 109.4 no H2071 . C207 . H2073 . 109.5 no H2072 . C207 . H2073 . 109.5 no C18 . N18 . C128 . 108.4(3) yes C18 . N18 . C138 . 124.6(2) yes C128 . N18 . C138 . 127.0(3) yes C198 . O28 . C208 . 114.7(4) yes N18 . C18 . C28 . 129.79(8) yes N18 . C18 . C68 . 108.31(19) yes C28 . C18 . C68 . 121.90(19) yes C18 . C28 . C38 . 118.06(8) yes C18 . C28 . H281 . 121.0 no C38 . C28 . H281 . 120.9 no C28 . C38 . C48 . 121.47(8) yes C28 . C38 . H381 . 119.3 no C48 . C38 . H381 . 119.2 no C38 . C48 . C58 . 120.67(8) yes C38 . C48 . H481 . 119.8 no C58 . C48 . H481 . 119.5 no C48 . C58 . C68 . 118.7(2) yes C48 . C58 . H581 . 120.7 no C68 . C58 . H581 . 120.6 no C58 . C68 . C18 . 119.16(8) yes C58 . C68 . C78 . 133.3(3) yes C18 . C68 . C78 . 107.5(3) yes C68 . C78 . C88 . 134.7(4) yes C68 . C78 . C128 . 105.6(3) yes C88 . C78 . C128 . 119.7(4) yes C78 . C88 . C98 . 117.2(4) yes C78 . C88 . H881 . 121.4 no C98 . C88 . H881 . 121.4 no C88 . C98 . C108 . 122.5(4) yes C88 . C98 . H981 . 118.8 no C108 . C98 . H981 . 118.7 no C98 . C108 . C118 . 120.9(4) yes C98 . C108 . H1081 . 119.6 no C118 . C108 . H1081 . 119.5 no C108 . C118 . C128 . 117.6(4) yes C108 . C118 . H1181 . 121.1 no C128 . C118 . H1181 . 121.3 no C78 . C128 . C118 . 122.0(4) yes C78 . C128 . N18 . 110.1(3) yes C118 . C128 . N18 . 127.8(4) yes N18 . C138 . C148 . 121.1(4) yes N18 . C138 . C188 . 118.6(4) yes C148 . C138 . C188 . 120.3(4) yes C138 . C148 . C158 . 118.7(4) yes C138 . C148 . C198 . 122.2(4) yes C158 . C148 . C198 . 119.1(3) yes C148 . C158 . C168 . 119.6(4) yes C148 . C158 . H1581 . 120.2 no C168 . C158 . H1581 . 120.2 no C158 . C168 . C178 . 121.6(4) yes C158 . C168 . H1681 . 119.2 no C178 . C168 . H1681 . 119.2 no C168 . C178 . C188 . 118.8(4) yes C168 . C178 . H1781 . 120.6 no C188 . C178 . H1781 . 120.6 no C178 . C188 . C138 . 121.0(4) yes C178 . C188 . H1881 . 119.5 no C138 . C188 . H1881 . 119.5 no C148 . C198 . O28 . 112.4(4) yes C148 . C198 . O18 . 124.6(3) yes O28 . C198 . O18 . 123.0(4) yes O28 . C208 . H2081 . 109.5 no O28 . C208 . H2083 . 109.4 no H2081 . C208 . H2083 . 109.5 no O28 . C208 . H2082 . 109.5 no H2081 . C208 . H2082 . 109.5 no H2083 . C208 . H2082 . 109.5 no _chemical_name_common 'Methyl 2-(9H-carbazol-9-yl)benzoate' _exptl_crystal_recrystallization_method ; A mixture of carbazole, methyl 2-iodobenzoate, copper powder, potassium carbonate and nitrobenzene were heated at 175 degrees C for 48 h. After cooling, the resultant mixture was a red solid. A mixture of water/chloroform (1:1) was added to the solid, and the two layers separated. The aqueous layer was then extracted twice with chloroform, and the organic layers were combined and dried over MgSO4. The solvent was removed under reduced pressure, and the residue oil was purified by flash dry chromatography on silica using hexane/ethyl acetate (85:15) as the eluant. This resulted in the formation of colourless crystals. (5.30 g, 88%) ; #edit data_ambient_293K_I.cif _database_code_depnum_ccdc_archive 'CCDC 745426' #_oxford_structure_analysis_title 'sp9016_293K in Pn' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 7.6837(2) _cell_length_b 15.5843(6) _cell_length_c 52.1546(16) _cell_angle_alpha 90 _cell_angle_beta 89.933(2) _cell_angle_gamma 90 _cell_volume 6245.3(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 n 1 ' _symmetry_space_group_name_Hall 'P -2yac' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y,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 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 16 # Given Formula = C20 H15 N1 O2 # Dc = 1.28 Fooo = 2528.00 Mu = 0.83 M = 2410.76 # Found Formula = C20 H15 N1 O2 # Dc = 1.28 FOOO = 2528.00 Mu = 0.83 M = 2410.76 _chemical_formula_sum 'C20 H15 N1 O2' _chemical_formula_moiety 'C20 H15 N1 O2' _chemical_compound_source ? _chemical_formula_weight 301.34 _cell_measurement_reflns_used 9965 _cell_measurement_theta_min 3 _cell_measurement_theta_max 23 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.52 _exptl_crystal_size_mid 0.53 _exptl_crystal_size_max 0.67 _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 2528 _exptl_absorpt_coefficient_mu 0.083 # Sheldrick geometric approximatio 0.96 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.79 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device 'Bruker SMART' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 293 _diffrn_reflns_number 40977 _reflns_number_total 8994 _diffrn_reflns_av_R_equivalents 0.0553 # Number of reflections with Friedels Law is 8994 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 8997 _diffrn_reflns_reduction_process ; Merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 ; _diffrn_reflns_theta_min 1.307 _diffrn_reflns_theta_max 23.273 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 23.273 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 57 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 17 _reflns_limit_l_min 0 _reflns_limit_l_max 57 #_oxford_diffrn_Wilson_B_factor 0.00 #_oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.11 _refine_diff_density_max 0.12 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement #_oxford_reflns_threshold_expression_ref I>2.0\s(I) _refine_ls_number_reflns 8409 _refine_ls_number_restraints 3082 _refine_ls_number_parameters 1658 #_oxford_refine_ls_R_factor_ref 0.0455 _refine_ls_wR_factor_ref 0.0399 _refine_ls_goodness_of_fit_ref 1.1069 _refine_ls_shift/su_max 0.005562 # The values computed from all data #_oxford_reflns_number_all 8948 _refine_ls_R_factor_all 0.0501 _refine_ls_wR_factor_all 0.0417 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 8409 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_gt 0.0399 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 2.65 -0.114 2.12 ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens N11 N -0.0850(9) 0.7002(4) -0.14035(12) 0.0488 1.0000 Uani D U . . . . . O11 O 0.0890(9) 0.6730(5) -0.09261(14) 0.0756 1.0000 Uani D U . . . . . O21 O -0.0986(9) 0.7133(4) -0.06332(11) 0.0658 1.0000 Uani D U . . . . . C121 C -0.0113(6) 0.7815(3) -0.13797(9) 0.0440 1.0000 Uani D U . . . . . C111 C -0.0632(7) 0.8500(4) -0.12283(9) 0.0514 1.0000 Uani D U . . . . . C101 C 0.0243(9) 0.9267(3) -0.12585(11) 0.0644 1.0000 Uani D U . . . . . C91 C 0.1588(8) 0.9348(3) -0.14339(10) 0.0603 1.0000 Uani D U . . . . . C81 C 0.2119(8) 0.8672(4) -0.15792(11) 0.0544 1.0000 Uani D U . . . . . C71 C 0.1291(10) 0.7898(4) -0.15574(11) 0.0446 1.0000 Uani D U . . . . . C61 C 0.1431(9) 0.7055(5) -0.16792(13) 0.0478 1.0000 Uani D U . . . . . C51 C 0.2629(10) 0.6753(7) -0.18876(14) 0.0625 1.0000 Uani D U . . . . . C41 C 0.2254(11) 0.5944(7) -0.19597(14) 0.0735 1.0000 Uani D U . . . . . C31 C 0.0995(12) 0.5460(7) -0.18578(16) 0.0731 1.0000 Uani D U . . . . . C21 C -0.0064(11) 0.5712(5) -0.16747(14) 0.0580 1.0000 Uani D U . . . . . C11 C 0.0229(10) 0.6527(5) -0.15933(12) 0.0448 1.0000 Uani D U . . . . . C131 C -0.2178(10) 0.6673(4) -0.12594(16) 0.0429 1.0000 Uani D U . . . . . C141 C -0.2148(10) 0.6550(4) -0.09902(15) 0.0462 1.0000 Uani D U . . . . . C151 C -0.3641(11) 0.6215(4) -0.08755(18) 0.0520 1.0000 Uani D U . . . . . C161 C -0.5064(12) 0.5978(4) -0.0996(2) 0.0653 1.0000 Uani D U . . . . . C171 C -0.5131(13) 0.6088(5) -0.1259(2) 0.0788 1.0000 Uani D U . . . . . C181 C -0.3736(12) 0.6429(5) -0.13999(19) 0.0704 1.0000 Uani D U . . . . . C191 C -0.0502(11) 0.6773(5) -0.08674(15) 0.0464 1.0000 Uani D U . . . . . C201 C 0.0492(17) 0.7389(7) -0.04709(19) 0.0812 1.0000 Uani D U . . . . . N12 N 0.0622(9) 0.2826(4) 0.00352(11) 0.0516 1.0000 Uani D U . . . . . O12 O -0.1273(8) 0.2063(5) -0.03580(14) 0.0784 1.0000 Uani D U . . . . . O22 O 0.0369(8) 0.1888(4) -0.07034(11) 0.0614 1.0000 Uani D U . . . . . C12 C -0.0006(7) 0.3657(3) 0.00037(10) 0.0583 1.0000 Uani D U . . . . . C22 C 0.0478(8) 0.4272(4) -0.01712(11) 0.0722 1.0000 Uani D U . . . . . C32 C -0.0450(10) 0.5026(4) -0.01737(13) 0.0945 1.0000 Uani D U . . . . . C42 C -0.1814(9) 0.5161(4) -0.00052(14) 0.0974 1.0000 Uani D U . . . . . C52 C -0.2323(9) 0.4539(5) 0.01666(14) 0.0919 1.0000 Uani D U . . . . . C62 C -0.1434(10) 0.3778(4) 0.01728(11) 0.0635 1.0000 Uani D U . . . . . C72 C -0.1674(10) 0.3047(6) 0.03106(16) 0.0582 1.0000 Uani D U . . . . . C82 C -0.2823(10) 0.2758(7) 0.05183(15) 0.0723 1.0000 Uani D U . . . . . C92 C -0.2626(11) 0.1936(7) 0.06117(15) 0.0825 1.0000 Uani D U . . . . . C102 C -0.1458(11) 0.1357(6) 0.05320(15) 0.0707 1.0000 Uani D U . . . . . C112 C -0.0340(10) 0.1602(5) 0.03365(13) 0.0537 1.0000 Uani D U . . . . . C122 C -0.0437(10) 0.2418(5) 0.02332(15) 0.0536 1.0000 Uani D U . . . . . C132 C 0.1928(10) 0.2403(4) -0.00836(13) 0.0398 1.0000 Uani D U . . . . . C142 C 0.1879(9) 0.1979(4) -0.03167(14) 0.0396 1.0000 Uani D U . . . . . C152 C 0.3287(10) 0.1568(5) -0.04170(17) 0.0613 1.0000 Uani D U . . . . . C162 C 0.4783(11) 0.1563(5) -0.03065(17) 0.0605 1.0000 Uani D U . . . . . C172 C 0.5015(11) 0.1981(4) -0.00768(16) 0.0570 1.0000 Uani D U . . . . . C182 C 0.3604(11) 0.2410(4) 0.00421(16) 0.0471 1.0000 Uani D U . . . . . C192 C 0.0165(10) 0.2003(5) -0.04636(15) 0.0397 1.0000 Uani D U . . . . . C202 C -0.1209(13) 0.1863(8) -0.08547(18) 0.0705 1.0000 Uani D U . . . . . N13 N 0.5453(8) 0.3769(3) 0.11416(11) 0.0430 1.0000 Uani D U . . . . . O13 O 0.3818(9) 0.4115(6) 0.16301(13) 0.0761 1.0000 Uani D U . . . . . O23 O 0.5653(9) 0.3622(4) 0.19150(10) 0.0600 1.0000 Uani D U . . . . . C13 C 0.4797(6) 0.2940(3) 0.11645(9) 0.0402 1.0000 Uani D U . . . . . C23 C 0.5346(7) 0.2276(3) 0.13206(10) 0.0498 1.0000 Uani D U . . . . . C33 C 0.4533(7) 0.1496(3) 0.12943(9) 0.0465 1.0000 Uani D U . . . . . C43 C 0.3183(8) 0.1382(3) 0.11196(11) 0.0562 1.0000 Uani D U . . . . . C53 C 0.2633(8) 0.2036(4) 0.09656(10) 0.0540 1.0000 Uani D U . . . . . C63 C 0.3403(9) 0.2828(4) 0.09866(10) 0.0437 1.0000 Uani D U . . . . . C73 C 0.3254(9) 0.3606(5) 0.08521(12) 0.0403 1.0000 Uani D U . . . . . C83 C 0.2198(11) 0.3931(7) 0.06561(13) 0.0582 1.0000 Uani D U . . . . . C93 C 0.2485(11) 0.4756(6) 0.05656(14) 0.0672 1.0000 Uani D U . . . . . C103 C 0.3725(11) 0.5265(6) 0.06579(15) 0.0586 1.0000 Uani D U . . . . . C113 C 0.4872(10) 0.4988(5) 0.08578(12) 0.0475 1.0000 Uani D U . . . . . C123 C 0.4563(9) 0.4168(5) 0.09444(11) 0.0365 1.0000 Uani D U . . . . . C133 C 0.6920(10) 0.4094(3) 0.12833(14) 0.0345 1.0000 Uani D U . . . . . C143 C 0.6863(10) 0.4176(3) 0.15395(15) 0.0358 1.0000 Uani D U . . . . . C153 C 0.8368(12) 0.4509(4) 0.16706(18) 0.0609 1.0000 Uani D U . . . . . C163 C 0.9751(12) 0.4768(4) 0.15453(18) 0.0649 1.0000 Uani D U . . . . . C173 C 0.9768(12) 0.4692(4) 0.1272(2) 0.0644 1.0000 Uani D U . . . . . C183 C 0.8418(11) 0.4368(4) 0.11356(18) 0.0537 1.0000 Uani D U . . . . . C193 C 0.5300(13) 0.3981(6) 0.16934(16) 0.0527 1.0000 Uani D U . . . . . C203 C 0.4265(14) 0.3322(7) 0.20809(17) 0.0749 1.0000 Uani D U . . . . . N14 N -0.0725(9) 0.1999(4) 0.25361(13) 0.0503 1.0000 Uani D U . . . . . O14 O 0.0913(9) 0.1604(5) 0.20334(15) 0.0848 1.0000 Uani D U . . . . . O24 O -0.0925(8) 0.2149(5) 0.17423(12) 0.0677 1.0000 Uani D U . . . . . C124 C -0.0092(7) 0.2832(3) 0.25230(9) 0.0467 1.0000 Uani D U . . . . . C114 C -0.0588(7) 0.3499(4) 0.23632(10) 0.0588 1.0000 Uani D U . . . . . C104 C 0.0290(7) 0.4272(3) 0.23873(11) 0.0566 1.0000 Uani D U . . . . . C94 C 0.1661(7) 0.4366(4) 0.25600(12) 0.0639 1.0000 Uani D U . . . . . C84 C 0.2159(7) 0.3707(5) 0.27171(12) 0.0596 1.0000 Uani D U . . . . . C74 C 0.1247(10) 0.2903(4) 0.26959(11) 0.0514 1.0000 Uani D U . . . . . C64 C 0.1431(10) 0.2125(6) 0.28323(13) 0.0479 1.0000 Uani D U . . . . . C54 C 0.2398(11) 0.1804(7) 0.30147(13) 0.0610 1.0000 Uani D U . . . . . C44 C 0.2363(12) 0.0972(7) 0.31091(17) 0.0721 1.0000 Uani D U . . . . . C34 C 0.1051(12) 0.0410(7) 0.29999(15) 0.0613 1.0000 Uani D U . . . . . C24 C -0.0066(12) 0.0712(6) 0.28035(14) 0.0558 1.0000 Uani D U . . . . . C14 C 0.0062(10) 0.1564(5) 0.27175(14) 0.0510 1.0000 Uani D U . . . . . C134 C -0.2232(11) 0.1658(4) 0.23953(17) 0.0492 1.0000 Uani D U . . . . . C144 C -0.2160(10) 0.1609(4) 0.21367(15) 0.0396 1.0000 Uani D U . . . . . C154 C -0.3563(11) 0.1309(4) 0.19946(19) 0.0559 1.0000 Uani D U . . . . . C164 C -0.5083(13) 0.1063(4) 0.2141(2) 0.0628 1.0000 Uani D U . . . . . C174 C -0.5126(12) 0.1121(4) 0.24014(19) 0.0546 1.0000 Uani D U . . . . . C184 C -0.3690(11) 0.1442(4) 0.25213(18) 0.0514 1.0000 Uani D U . . . . . C194 C -0.0591(11) 0.1808(6) 0.19632(16) 0.0535 1.0000 Uani D U . . . . . C204 C 0.0475(14) 0.2398(8) 0.1581(2) 0.0819 1.0000 Uani D U . . . . . N15 N 0.0491(9) 0.1248(4) 0.49919(13) 0.0533 1.0000 Uani D U . . . . . O15 O -0.1189(9) 0.0866(5) 0.44963(14) 0.0765 1.0000 Uani D U . . . . . O25 O 0.0731(8) 0.1421(4) 0.42127(12) 0.0593 1.0000 Uani D U . . . . . C15 C -0.0190(6) 0.2070(3) 0.49664(11) 0.0556 1.0000 Uani D U . . . . . C25 C 0.0343(7) 0.2730(4) 0.48094(11) 0.0593 1.0000 Uani D U . . . . . C35 C -0.0502(9) 0.3509(4) 0.48328(13) 0.0785 1.0000 Uani D U . . . . . C45 C -0.1833(9) 0.3625(4) 0.50096(14) 0.0752 1.0000 Uani D U . . . . . C55 C -0.2386(8) 0.2967(5) 0.51635(13) 0.0741 1.0000 Uani D U . . . . . C65 C -0.1526(9) 0.2161(4) 0.51422(13) 0.0577 1.0000 Uani D U . . . . . C75 C -0.1740(10) 0.1352(6) 0.52770(15) 0.0606 1.0000 Uani D U . . . . . C85 C -0.2854(12) 0.1105(8) 0.54726(17) 0.0763 1.0000 Uani D U . . . . . C95 C -0.2747(11) 0.0331(7) 0.55708(16) 0.0838 1.0000 Uani D U . . . . . C105 C -0.1383(13) -0.0265(8) 0.54714(17) 0.0833 1.0000 Uani D U . . . . . C115 C -0.0331(11) -0.0007(6) 0.52836(15) 0.0691 1.0000 Uani D U . . . . . C125 C -0.0469(10) 0.0796(6) 0.51792(15) 0.0590 1.0000 Uani D U . . . . . C135 C 0.1899(11) 0.0889(4) 0.48600(16) 0.0514 1.0000 Uani D U . . . . . C145 C 0.1855(10) 0.0795(4) 0.45831(17) 0.0459 1.0000 Uani D U . . . . . C155 C 0.3276(10) 0.0518(4) 0.44628(17) 0.0497 1.0000 Uani D U . . . . . C165 C 0.4801(10) 0.0306(4) 0.46057(17) 0.0563 1.0000 Uani D U . . . . . C175 C 0.4853(11) 0.0383(4) 0.48609(19) 0.0650 1.0000 Uani D U . . . . . C185 C 0.3342(11) 0.0702(5) 0.49775(17) 0.0597 1.0000 Uani D U . . . . . C195 C 0.0243(10) 0.1042(5) 0.44328(16) 0.0415 1.0000 Uani D U . . . . . C205 C -0.0738(15) 0.1662(6) 0.4051(2) 0.0734 1.0000 Uani D U . . . . . N16 N 0.5562(8) 0.2189(4) 0.60731(12) 0.0489 1.0000 Uani D U . . . . . O16 O 0.3756(9) 0.2773(5) 0.64938(15) 0.0815 1.0000 Uani D U . . . . . O26 O 0.5312(9) 0.3183(4) 0.68298(11) 0.0649 1.0000 Uani D U . . . . . C16 C 0.4977(6) 0.1382(3) 0.61479(10) 0.0509 1.0000 Uani D U . . . . . C26 C 0.5671(7) 0.0821(4) 0.63285(11) 0.0591 1.0000 Uani D U . . . . . C36 C 0.4907(8) 0.0017(3) 0.63523(10) 0.0660 1.0000 Uani D U . . . . . C46 C 0.3533(8) -0.0224(3) 0.61994(13) 0.0823 1.0000 Uani D U . . . . . C56 C 0.2862(7) 0.0314(4) 0.60222(12) 0.0710 1.0000 Uani D U . . . . . C66 C 0.3593(9) 0.1142(4) 0.59926(11) 0.0609 1.0000 Uani D U . . . . . C76 C 0.3287(10) 0.1904(7) 0.58172(17) 0.0643 1.0000 Uani D U . . . . . C86 C 0.2122(11) 0.2085(8) 0.56298(17) 0.0842 1.0000 Uani D U . . . . . C96 C 0.2134(11) 0.2861(8) 0.55122(19) 0.0925 1.0000 Uani D U . . . . . C106 C 0.3417(12) 0.3444(7) 0.55954(16) 0.0833 1.0000 Uani D U . . . . . C116 C 0.4631(11) 0.3274(6) 0.57840(15) 0.0669 1.0000 Uani D U . . . . . C126 C 0.4552(9) 0.2492(6) 0.58910(14) 0.0491 1.0000 Uani D U . . . . . C136 C 0.7071(10) 0.2618(4) 0.61957(14) 0.0397 1.0000 Uani D U . . . . . C146 C 0.6735(9) 0.2985(4) 0.64442(13) 0.0415 1.0000 Uani D U . . . . . C156 C 0.8200(10) 0.3422(4) 0.65463(14) 0.0397 1.0000 Uani D U . . . . . C166 C 0.9831(10) 0.3452(4) 0.64068(15) 0.0511 1.0000 Uani D U . . . . . C176 C 0.9957(12) 0.3049(5) 0.61731(16) 0.0622 1.0000 Uani D U . . . . . C186 C 0.8586(12) 0.2652(5) 0.60786(17) 0.0645 1.0000 Uani D U . . . . . C196 C 0.5088(12) 0.2962(6) 0.65763(17) 0.0584 1.0000 Uani D U . . . . . C206 C 0.3767(16) 0.3154(9) 0.6991(2) 0.0902 1.0000 Uani D U . . . . . N17 N -0.1020(9) 0.2075(4) 0.74888(12) 0.0555 1.0000 Uani D U . . . . . O17 O 0.0711(9) 0.1504(5) 0.70774(12) 0.0817 1.0000 Uani D U . . . . . O27 O -0.0848(10) 0.1072(5) 0.67479(13) 0.0771 1.0000 Uani D U . . . . . C17 C 0.0018(6) 0.1728(3) 0.76798(10) 0.0497 1.0000 Uani D U . . . . . C27 C -0.0086(7) 0.0936(3) 0.77966(11) 0.0584 1.0000 Uani D U . . . . . C37 C 0.1052(9) 0.0769(4) 0.79942(12) 0.0775 1.0000 Uani D U . . . . . C47 C 0.2281(8) 0.1369(5) 0.80692(11) 0.0778 1.0000 Uani D U . . . . . C57 C 0.2413(8) 0.2145(5) 0.79500(13) 0.0645 1.0000 Uani D U . . . . . C67 C 0.1336(9) 0.2342(4) 0.77557(13) 0.0543 1.0000 Uani D U . . . . . C77 C 0.1016(10) 0.3098(6) 0.75883(15) 0.0536 1.0000 Uani D U . . . . . C87 C 0.1742(11) 0.3880(6) 0.75687(18) 0.0660 1.0000 Uani D U . . . . . C97 C 0.1125(12) 0.4449(6) 0.73988(19) 0.0775 1.0000 Uani D U . . . . . C107 C -0.0334(14) 0.4245(6) 0.72308(19) 0.0779 1.0000 Uani D U . . . . . C117 C -0.1135(12) 0.3480(6) 0.72415(15) 0.0614 1.0000 Uani D U . . . . . C127 C -0.0373(11) 0.2875(5) 0.74315(14) 0.0528 1.0000 Uani D U . . . . . C137 C -0.2421(11) 0.1605(4) 0.73707(14) 0.0424 1.0000 Uani D U . . . . . C147 C -0.2262(10) 0.1212(3) 0.71320(13) 0.0375 1.0000 Uani D U . . . . . C157 C -0.3684(12) 0.0802(4) 0.70380(17) 0.0524 1.0000 Uani D U . . . . . C167 C -0.5239(11) 0.0782(4) 0.71786(16) 0.0526 1.0000 Uani D U . . . . . C177 C -0.5469(12) 0.1147(4) 0.74091(17) 0.0549 1.0000 Uani D U . . . . . C187 C -0.4070(10) 0.1568(4) 0.75104(15) 0.0497 1.0000 Uani D U . . . . . C197 C -0.0584(13) 0.1250(5) 0.70056(17) 0.0582 1.0000 Uani D U . . . . . C207 C 0.0788(16) 0.1041(8) 0.6596(2) 0.0926 1.0000 Uani D U . . . . . N18 N 0.3941(7) 0.2906(3) 0.86201(10) 0.0348 1.0000 Uani D U . . . . . O18 O 0.5847(8) 0.3702(5) 0.90232(13) 0.0749 1.0000 Uani D U . . . . . O28 O 0.4222(8) 0.3944(5) 0.93656(11) 0.0587 1.0000 Uani D U . . . . . C18 C 0.4987(6) 0.3210(3) 0.84262(9) 0.0382 1.0000 Uani D U . . . . . C28 C 0.4963(7) 0.3998(3) 0.83055(11) 0.0515 1.0000 Uani D U . . . . . C38 C 0.6187(9) 0.4147(3) 0.81190(10) 0.0625 1.0000 Uani D U . . . . . C48 C 0.7401(8) 0.3522(4) 0.80525(11) 0.0751 1.0000 Uani D U . . . . . C58 C 0.7431(8) 0.2741(4) 0.81722(11) 0.0598 1.0000 Uani D U . . . . . C68 C 0.6157(9) 0.2586(3) 0.83693(10) 0.0393 1.0000 Uani D U . . . . . C78 C 0.5854(9) 0.1875(5) 0.85299(14) 0.0422 1.0000 Uani D U . . . . . C88 C 0.6638(11) 0.1042(5) 0.85587(15) 0.0567 1.0000 Uani D U . . . . . C98 C 0.5946(11) 0.0494(5) 0.87483(15) 0.0598 1.0000 Uani D U . . . . . C108 C 0.4612(11) 0.0752(5) 0.88920(16) 0.0546 1.0000 Uani D U . . . . . C118 C 0.3837(10) 0.1556(5) 0.88611(14) 0.0476 1.0000 Uani D U . . . . . C128 C 0.4456(8) 0.2072(4) 0.86849(13) 0.0352 1.0000 Uani D U . . . . . C138 C 0.2498(9) 0.3342(4) 0.87401(13) 0.0369 1.0000 Uani D U . . . . . C148 C 0.2733(10) 0.3761(4) 0.89712(13) 0.0451 1.0000 Uani D U . . . . . C158 C 0.1276(11) 0.4232(5) 0.90757(16) 0.0550 1.0000 Uani D U . . . . . C168 C -0.0271(11) 0.4258(5) 0.89563(16) 0.0583 1.0000 Uani D U . . . . . C178 C -0.0375(11) 0.3795(5) 0.87239(17) 0.0590 1.0000 Uani D U . . . . . C188 C 0.1045(10) 0.3350(4) 0.86213(16) 0.0541 1.0000 Uani D U . . . . . C198 C 0.4398(10) 0.3756(5) 0.91286(15) 0.0463 1.0000 Uani D U . . . . . C208 C 0.5692(14) 0.3933(7) 0.95232(18) 0.0745 1.0000 Uani D U . . . . . H1111 H -0.1559 0.8442 -0.1109 0.0645 1.0000 Uiso R . . . . . . H1011 H -0.0083 0.9746 -0.1156 0.0812 1.0000 Uiso R . . . . . . H911 H 0.2142 0.9889 -0.1454 0.0771 1.0000 Uiso R . . . . . . H811 H 0.3065 0.8737 -0.1695 0.0692 1.0000 Uiso R . . . . . . H511 H 0.3537 0.7091 -0.1959 0.0746 1.0000 Uiso R . . . . . . H411 H 0.2938 0.5705 -0.2094 0.0842 1.0000 Uiso R . . . . . . H311 H 0.0860 0.4893 -0.1922 0.0876 1.0000 Uiso R . . . . . . H211 H -0.0959 0.5359 -0.1606 0.0687 1.0000 Uiso R . . . . . . H1511 H -0.3631 0.6150 -0.0694 0.0614 1.0000 Uiso R . . . . . . H1611 H -0.6023 0.5737 -0.0906 0.0777 1.0000 Uiso R . . . . . . H1711 H -0.6152 0.5924 -0.1349 0.0928 1.0000 Uiso R . . . . . . H1811 H -0.3791 0.6504 -0.1581 0.0823 1.0000 Uiso R . . . . . . H2011 H 0.0085 0.7417 -0.0293 0.0893 1.0000 Uiso R . . . . . . H2012 H 0.0928 0.7946 -0.0531 0.0897 1.0000 Uiso R . . . . . . H2013 H 0.1418 0.6957 -0.0487 0.0899 1.0000 Uiso R . . . . . . H221 H 0.1417 0.4181 -0.0287 0.0866 1.0000 Uiso R . . . . . . H321 H -0.0150 0.5463 -0.0293 0.1138 1.0000 Uiso R . . . . . . H421 H -0.2414 0.5694 -0.0007 0.1174 1.0000 Uiso R . . . . . . H521 H -0.3269 0.4637 0.0280 0.1110 1.0000 Uiso R . . . . . . H821 H -0.3688 0.3128 0.0587 0.0835 1.0000 Uiso R . . . . . . H921 H -0.3393 0.1767 0.0745 0.0955 1.0000 Uiso R . . . . . . H1021 H -0.1409 0.0800 0.0606 0.0851 1.0000 Uiso R . . . . . . H1121 H 0.0498 0.1206 0.0274 0.0631 1.0000 Uiso R . . . . . . H1521 H 0.3165 0.1274 -0.0575 0.0720 1.0000 Uiso R . . . . . . H1621 H 0.5733 0.1268 -0.0383 0.0724 1.0000 Uiso R . . . . . . H1721 H 0.6129 0.1976 0.0002 0.0686 1.0000 Uiso R . . . . . . H1821 H 0.3763 0.2698 0.0201 0.0562 1.0000 Uiso R . . . . . . H2021 H -0.0885 0.1916 -0.1036 0.0900 1.0000 Uiso R . . . . . . H2022 H -0.1967 0.2340 -0.0803 0.0897 1.0000 Uiso R . . . . . . H2023 H -0.1784 0.1310 -0.0824 0.0892 1.0000 Uiso R . . . . . . H231 H 0.6260 0.2353 0.1441 0.0606 1.0000 Uiso R . . . . . . H331 H 0.4902 0.1024 0.1396 0.0557 1.0000 Uiso R . . . . . . H431 H 0.2620 0.0840 0.1108 0.0688 1.0000 Uiso R . . . . . . H531 H 0.1722 0.1947 0.0846 0.0649 1.0000 Uiso R . . . . . . H831 H 0.1296 0.3590 0.0585 0.0687 1.0000 Uiso R . . . . . . H931 H 0.1764 0.4966 0.0432 0.0790 1.0000 Uiso R . . . . . . H1031 H 0.3849 0.5826 0.0589 0.0683 1.0000 Uiso R . . . . . . H1131 H 0.5767 0.5341 0.0926 0.0551 1.0000 Uiso R . . . . . . H1531 H 0.8358 0.4539 0.1853 0.0724 1.0000 Uiso R . . . . . . H1631 H 1.0713 0.5005 0.1635 0.0760 1.0000 Uiso R . . . . . . H1731 H 1.0780 0.4876 0.1183 0.0780 1.0000 Uiso R . . . . . . H1831 H 0.8459 0.4322 0.0954 0.0642 1.0000 Uiso R . . . . . . H2031 H 0.4593 0.3447 0.2259 0.0892 1.0000 Uiso R . . . . . . H2032 H 0.3196 0.3640 0.2039 0.0904 1.0000 Uiso R . . . . . . H2033 H 0.4090 0.2705 0.2057 0.0911 1.0000 Uiso R . . . . . . H1141 H -0.1496 0.3431 0.2242 0.0685 1.0000 Uiso R . . . . . . H1041 H -0.0046 0.4748 0.2285 0.0669 1.0000 Uiso R . . . . . . H941 H 0.2269 0.4896 0.2569 0.0759 1.0000 Uiso R . . . . . . H841 H 0.3080 0.3779 0.2837 0.0697 1.0000 Uiso R . . . . . . H541 H 0.3216 0.2181 0.3092 0.0780 1.0000 Uiso R . . . . . . H441 H 0.3150 0.0776 0.3237 0.0947 1.0000 Uiso R . . . . . . H341 H 0.0938 -0.0163 0.3060 0.0799 1.0000 Uiso R . . . . . . H241 H -0.0902 0.0336 0.2730 0.0690 1.0000 Uiso R . . . . . . H1541 H -0.3519 0.1271 0.1813 0.0680 1.0000 Uiso R . . . . . . H1641 H -0.6075 0.0858 0.2051 0.0759 1.0000 Uiso R . . . . . . H1741 H -0.6121 0.0941 0.2495 0.0669 1.0000 Uiso R . . . . . . H1841 H -0.3741 0.1517 0.2702 0.0630 1.0000 Uiso R . . . . . . H2041 H 0.0024 0.2767 0.1444 0.0899 1.0000 Uiso R . . . . . . H2042 H 0.1365 0.2706 0.1680 0.0889 1.0000 Uiso R . . . . . . H2043 H 0.1006 0.1886 0.1505 0.0905 1.0000 Uiso R . . . . . . H251 H 0.1253 0.2649 0.4688 0.0703 1.0000 Uiso R . . . . . . H351 H -0.0177 0.3970 0.4724 0.0941 1.0000 Uiso R . . . . . . H451 H -0.2351 0.4175 0.5026 0.0894 1.0000 Uiso R . . . . . . H551 H -0.3315 0.3049 0.5281 0.0860 1.0000 Uiso R . . . . . . H851 H -0.3704 0.1496 0.5535 0.0920 1.0000 Uiso R . . . . . . H951 H -0.3519 0.0154 0.5703 0.1003 1.0000 Uiso R . . . . . . H1051 H -0.1271 -0.0825 0.5541 0.0998 1.0000 Uiso R . . . . . . H1151 H 0.0538 -0.0390 0.5223 0.0838 1.0000 Uiso R . . . . . . H1551 H 0.3277 0.0457 0.4282 0.0586 1.0000 Uiso R . . . . . . H1651 H 0.5810 0.0105 0.4519 0.0674 1.0000 Uiso R . . . . . . H1751 H 0.5853 0.0234 0.4958 0.0750 1.0000 Uiso R . . . . . . H1851 H 0.3370 0.0786 0.5158 0.0743 1.0000 Uiso R . . . . . . H2051 H -0.0306 0.1965 0.3898 0.0899 1.0000 Uiso R . . . . . . H2052 H -0.1526 0.2033 0.4150 0.0906 1.0000 Uiso R . . . . . . H2053 H -0.1363 0.1142 0.3997 0.0890 1.0000 Uiso R . . . . . . H261 H 0.6634 0.0984 0.6432 0.0700 1.0000 Uiso R . . . . . . H361 H 0.5345 -0.0373 0.6476 0.0787 1.0000 Uiso R . . . . . . H461 H 0.3043 -0.0779 0.6220 0.0989 1.0000 Uiso R . . . . . . H561 H 0.1909 0.0138 0.5919 0.0852 1.0000 Uiso R . . . . . . H861 H 0.1290 0.1664 0.5582 0.1014 1.0000 Uiso R . . . . . . H961 H 0.1327 0.3003 0.5381 0.1127 1.0000 Uiso R . . . . . . H1061 H 0.3457 0.3991 0.5515 0.0981 1.0000 Uiso R . . . . . . H1161 H 0.5470 0.3686 0.5836 0.0803 1.0000 Uiso R . . . . . . H1561 H 0.8102 0.3700 0.6708 0.0483 1.0000 Uiso R . . . . . . H1661 H 1.0802 0.3746 0.6477 0.0617 1.0000 Uiso R . . . . . . H1761 H 1.1021 0.3052 0.6080 0.0744 1.0000 Uiso R . . . . . . H1861 H 0.8693 0.2376 0.5917 0.0774 1.0000 Uiso R . . . . . . H2061 H 0.3540 0.2551 0.7034 0.0895 1.0000 Uiso R . . . . . . H2062 H 0.2760 0.3387 0.6900 0.0903 1.0000 Uiso R . . . . . . H2063 H 0.4007 0.3488 0.7146 0.0893 1.0000 Uiso R . . . . . . H271 H -0.0913 0.0522 0.7742 0.0703 1.0000 Uiso R . . . . . . H371 H 0.0996 0.0232 0.8080 0.0927 1.0000 Uiso R . . . . . . H471 H 0.3041 0.1237 0.8207 0.0927 1.0000 Uiso R . . . . . . H571 H 0.3272 0.2545 0.8004 0.0780 1.0000 Uiso R . . . . . . H871 H 0.2698 0.4032 0.7675 0.0802 1.0000 Uiso R . . . . . . H971 H 0.1652 0.4998 0.7386 0.0929 1.0000 Uiso R . . . . . . H1071 H -0.0735 0.4659 0.7111 0.0952 1.0000 Uiso R . . . . . . H1171 H -0.2108 0.3337 0.7138 0.0742 1.0000 Uiso R . . . . . . H1571 H -0.3630 0.0527 0.6876 0.0638 1.0000 Uiso R . . . . . . H1671 H -0.6197 0.0485 0.7105 0.0634 1.0000 Uiso R . . . . . . H1771 H -0.6550 0.1112 0.7497 0.0655 1.0000 Uiso R . . . . . . H1871 H -0.4170 0.1845 0.7672 0.0608 1.0000 Uiso R . . . . . . H2071 H 0.0567 0.0664 0.6449 0.0902 1.0000 Uiso R . . . . . . H2072 H 0.1745 0.0815 0.6700 0.0906 1.0000 Uiso R . . . . . . H2073 H 0.1063 0.1624 0.6537 0.0902 1.0000 Uiso R . . . . . . H281 H 0.4132 0.4424 0.8350 0.0617 1.0000 Uiso R . . . . . . H381 H 0.6202 0.4683 0.8033 0.0749 1.0000 Uiso R . . . . . . H481 H 0.8227 0.3640 0.7922 0.0904 1.0000 Uiso R . . . . . . H581 H 0.8263 0.2316 0.8127 0.0707 1.0000 Uiso R . . . . . . H881 H 0.7584 0.0870 0.8453 0.0663 1.0000 Uiso R . . . . . . H981 H 0.6434 -0.0060 0.8772 0.0710 1.0000 Uiso R . . . . . . H1081 H 0.4180 0.0373 0.9020 0.0637 1.0000 Uiso R . . . . . . H1181 H 0.2888 0.1727 0.8966 0.0551 1.0000 Uiso R . . . . . . H1581 H 0.1417 0.4527 0.9234 0.0658 1.0000 Uiso R . . . . . . H1681 H -0.1234 0.4568 0.9023 0.0704 1.0000 Uiso R . . . . . . H1781 H -0.1451 0.3782 0.8634 0.0706 1.0000 Uiso R . . . . . . H1881 H 0.0927 0.3060 0.8462 0.0637 1.0000 Uiso R . . . . . . H2081 H 0.6383 0.3426 0.9477 0.0888 1.0000 Uiso R . . . . . . H2082 H 0.5301 0.3900 0.9702 0.0896 1.0000 Uiso R . . . . . . H2083 H 0.6359 0.4460 0.9492 0.0898 1.0000 Uiso 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 0.049(3) 0.050(3) 0.047(3) -0.007(2) 0.007(2) -0.010(2) O11 0.043(2) 0.103(4) 0.081(3) -0.003(3) -0.007(3) -0.008(3) O21 0.083(4) 0.074(3) 0.041(2) -0.002(2) -0.014(2) 0.006(3) C121 0.044(4) 0.057(3) 0.032(3) -0.006(2) -0.007(2) -0.015(3) C111 0.056(5) 0.065(3) 0.033(3) -0.011(3) -0.003(3) -0.014(3) C101 0.088(5) 0.052(3) 0.054(4) -0.011(3) 0.004(3) -0.009(3) C91 0.088(5) 0.059(3) 0.034(3) 0.009(3) -0.010(3) -0.024(4) C81 0.061(5) 0.066(3) 0.036(3) 0.019(3) 0.000(3) -0.008(3) C71 0.042(4) 0.066(3) 0.025(3) 0.001(2) -0.011(2) -0.009(3) C61 0.036(3) 0.070(3) 0.038(3) -0.005(3) -0.007(2) -0.004(2) C51 0.047(3) 0.084(4) 0.056(4) 0.000(3) 0.007(3) 0.008(3) C41 0.093(5) 0.084(4) 0.044(4) -0.007(3) 0.026(3) 0.010(4) C31 0.096(5) 0.071(4) 0.053(4) -0.012(3) 0.016(3) 0.002(3) C21 0.070(4) 0.059(3) 0.045(4) -0.011(3) 0.006(3) -0.007(3) C11 0.041(3) 0.061(3) 0.032(3) -0.010(2) -0.009(2) -0.004(2) C131 0.038(3) 0.039(3) 0.052(2) 0.002(3) -0.0011(19) 0.000(3) C141 0.042(3) 0.045(4) 0.051(2) 0.007(3) -0.001(2) -0.003(3) C151 0.051(3) 0.042(3) 0.063(3) 0.004(3) 0.013(2) 0.001(3) C161 0.035(3) 0.068(4) 0.093(3) 0.003(4) 0.018(3) -0.002(3) C171 0.043(4) 0.103(5) 0.090(3) -0.011(5) -0.005(3) -0.016(4) C181 0.052(3) 0.099(5) 0.060(3) -0.019(4) -0.005(3) -0.016(4) C191 0.047(2) 0.040(3) 0.053(3) 0.001(3) -0.006(2) 0.005(3) C201 0.105(5) 0.079(5) 0.060(4) -0.003(4) -0.028(4) -0.011(5) N12 0.044(3) 0.069(3) 0.042(3) -0.003(2) 0.003(2) 0.011(2) O12 0.034(2) 0.134(4) 0.066(3) -0.027(3) 0.003(2) 0.001(3) O22 0.045(3) 0.099(4) 0.041(2) 0.005(3) -0.0019(19) 0.004(3) C12 0.049(4) 0.055(3) 0.070(4) -0.018(2) -0.015(3) -0.001(3) C22 0.073(4) 0.063(4) 0.081(4) -0.003(3) -0.025(3) 0.001(3) C32 0.107(5) 0.066(4) 0.111(5) -0.003(4) -0.040(4) 0.013(4) C42 0.097(5) 0.064(4) 0.131(5) -0.031(3) -0.047(4) 0.026(4) C52 0.079(5) 0.089(4) 0.108(5) -0.035(3) -0.026(4) 0.032(3) C62 0.051(4) 0.066(3) 0.074(4) -0.039(3) -0.018(3) 0.006(3) C72 0.042(4) 0.080(3) 0.052(4) -0.037(3) -0.004(3) 0.004(3) C82 0.051(4) 0.112(4) 0.054(4) -0.052(3) 0.011(3) 0.004(3) C92 0.065(4) 0.130(4) 0.052(4) -0.023(3) 0.021(3) -0.008(4) C102 0.064(4) 0.096(4) 0.052(4) -0.001(3) 0.010(3) -0.011(3) C112 0.046(4) 0.076(3) 0.039(3) -0.007(3) 0.001(2) 0.003(3) C122 0.043(4) 0.064(3) 0.054(4) -0.018(2) 0.011(3) -0.003(3) C132 0.034(2) 0.051(3) 0.034(3) 0.008(2) -0.0002(19) 0.004(3) C142 0.035(2) 0.028(3) 0.055(3) -0.006(3) -0.004(2) -0.002(2) C152 0.030(2) 0.085(5) 0.069(4) -0.023(4) 0.006(3) -0.004(3) C162 0.026(3) 0.085(5) 0.071(4) -0.014(3) 0.011(3) -0.006(3) C172 0.029(3) 0.072(4) 0.070(4) -0.006(3) 0.002(3) -0.012(3) C182 0.036(3) 0.055(4) 0.050(3) -0.005(3) -0.006(2) -0.009(3) C192 0.034(2) 0.039(3) 0.045(2) 0.000(3) 0.0010(18) -0.005(3) C202 0.053(4) 0.103(5) 0.055(4) -0.005(4) -0.012(3) -0.009(4) N13 0.049(3) 0.048(2) 0.031(2) -0.007(2) -0.0016(19) -0.017(2) O13 0.052(3) 0.118(5) 0.058(3) 0.014(3) 0.008(3) 0.008(4) O23 0.057(3) 0.082(4) 0.040(2) -0.002(2) 0.006(2) -0.009(3) C13 0.049(4) 0.043(2) 0.029(3) -0.013(2) 0.012(2) -0.012(2) C23 0.048(4) 0.048(3) 0.053(4) -0.003(3) 0.006(3) -0.013(3) C33 0.064(4) 0.046(3) 0.030(3) -0.011(3) 0.026(2) -0.014(3) C43 0.069(4) 0.057(3) 0.042(4) -0.014(3) 0.022(3) -0.025(3) C53 0.071(4) 0.065(3) 0.026(3) -0.017(2) 0.011(3) -0.030(3) C63 0.053(3) 0.056(2) 0.022(3) -0.016(2) 0.013(2) -0.018(3) C73 0.044(3) 0.051(3) 0.026(3) -0.021(2) 0.006(2) -0.006(2) C83 0.055(4) 0.090(4) 0.029(3) -0.011(3) -0.004(2) -0.015(3) C93 0.060(4) 0.099(4) 0.043(3) 0.009(3) -0.009(3) -0.002(3) C103 0.058(4) 0.064(4) 0.054(4) 0.008(3) 0.004(3) 0.004(3) C113 0.054(4) 0.044(2) 0.044(3) -0.012(2) -0.001(2) -0.002(3) C123 0.043(3) 0.042(2) 0.024(3) -0.0182(19) 0.006(2) -0.003(2) C133 0.035(2) 0.027(3) 0.041(2) -0.006(3) -0.0019(18) -0.003(2) C143 0.050(3) 0.016(3) 0.0411(19) -0.011(2) -0.004(2) -0.007(3) C153 0.064(4) 0.065(4) 0.054(3) 0.015(3) -0.025(2) -0.025(3) C163 0.063(4) 0.048(4) 0.084(3) -0.005(4) -0.012(3) -0.026(3) C173 0.051(4) 0.060(4) 0.082(3) 0.007(4) 0.004(3) -0.024(3) C183 0.060(3) 0.045(3) 0.057(3) 0.004(3) 0.009(2) -0.020(3) C193 0.053(2) 0.067(4) 0.039(3) -0.011(3) -0.002(2) -0.009(3) C203 0.066(4) 0.109(6) 0.050(4) -0.003(4) 0.027(3) 0.009(4) N14 0.039(3) 0.057(3) 0.055(3) 0.000(2) -0.016(2) -0.004(2) O14 0.040(2) 0.126(5) 0.088(4) 0.016(4) -0.009(3) 0.029(3) O24 0.032(2) 0.108(4) 0.063(3) 0.012(3) -0.005(2) 0.005(3) C124 0.041(3) 0.048(2) 0.051(3) -0.016(2) -0.008(2) 0.008(2) C114 0.051(4) 0.056(3) 0.069(4) -0.004(3) -0.007(3) 0.013(3) C104 0.042(3) 0.067(3) 0.061(4) 0.005(3) 0.024(2) 0.003(3) C94 0.038(3) 0.078(4) 0.075(4) -0.001(3) 0.025(3) -0.015(3) C84 0.040(4) 0.085(3) 0.053(4) -0.013(3) 0.004(3) -0.014(3) C74 0.043(4) 0.062(3) 0.050(4) -0.018(3) -0.007(3) 0.006(3) C64 0.044(4) 0.070(3) 0.029(3) -0.018(2) -0.007(2) 0.009(2) C54 0.055(4) 0.086(3) 0.042(3) -0.013(3) -0.015(3) 0.015(3) C44 0.057(5) 0.090(4) 0.069(5) -0.001(3) -0.018(4) 0.028(4) C34 0.055(5) 0.072(4) 0.057(4) -0.002(3) 0.001(3) 0.027(3) C24 0.050(4) 0.054(3) 0.064(4) -0.005(3) -0.007(3) 0.016(3) C14 0.043(4) 0.049(2) 0.061(4) -0.012(2) -0.016(3) 0.018(2) C134 0.039(3) 0.054(4) 0.055(2) 0.005(3) -0.012(2) -0.007(3) C144 0.039(2) 0.026(3) 0.054(2) 0.001(3) -0.0121(19) 0.008(2) C154 0.045(3) 0.059(4) 0.064(3) 0.009(3) -0.024(2) 0.002(3) C164 0.049(3) 0.052(4) 0.087(3) -0.002(4) -0.017(3) -0.009(3) C174 0.038(3) 0.041(3) 0.086(3) 0.016(3) -0.005(3) 0.000(3) C184 0.044(3) 0.044(4) 0.066(3) -0.011(3) 0.004(2) 0.003(3) C194 0.035(2) 0.075(4) 0.051(3) -0.011(3) -0.010(2) 0.011(3) C204 0.056(4) 0.117(6) 0.072(5) -0.004(4) 0.019(4) 0.004(5) N15 0.043(3) 0.061(3) 0.056(3) -0.006(2) 0.014(2) -0.013(2) O15 0.034(2) 0.105(4) 0.090(4) 0.009(4) 0.007(3) -0.023(3) O25 0.056(3) 0.051(3) 0.071(3) 0.016(2) -0.005(2) -0.016(3) C15 0.032(3) 0.060(3) 0.075(4) -0.010(3) 0.004(3) -0.015(2) C25 0.046(4) 0.060(3) 0.072(4) -0.006(3) 0.003(3) -0.009(3) C35 0.068(5) 0.063(3) 0.104(5) -0.007(4) -0.003(4) 0.000(4) C45 0.064(5) 0.074(4) 0.088(5) -0.024(3) -0.020(3) 0.015(4) C55 0.036(4) 0.091(3) 0.096(5) -0.022(4) -0.010(3) 0.005(3) C65 0.025(3) 0.075(3) 0.073(4) -0.014(3) -0.001(3) -0.012(3) C75 0.035(4) 0.086(3) 0.060(4) -0.008(3) 0.008(3) -0.017(3) C85 0.052(4) 0.105(4) 0.072(5) -0.015(4) 0.024(3) -0.017(4) C95 0.065(4) 0.109(4) 0.077(5) -0.006(3) 0.038(4) -0.041(4) C105 0.086(5) 0.086(4) 0.078(5) 0.013(4) 0.029(4) -0.025(4) C115 0.057(4) 0.085(3) 0.066(4) 0.010(3) 0.018(3) -0.009(3) C125 0.037(4) 0.079(3) 0.061(4) 0.004(3) 0.011(3) -0.014(3) C135 0.037(3) 0.067(4) 0.050(2) 0.006(3) 0.0080(19) -0.004(3) C145 0.026(2) 0.060(4) 0.051(2) -0.003(3) 0.004(2) -0.012(3) C155 0.032(2) 0.057(4) 0.059(3) -0.019(3) 0.005(2) -0.014(3) C165 0.021(3) 0.074(4) 0.074(3) -0.004(3) 0.019(2) -0.002(3) C175 0.031(3) 0.089(5) 0.075(3) -0.003(4) -0.005(3) -0.010(3) C185 0.046(3) 0.093(5) 0.040(3) 0.003(4) 0.001(2) -0.006(3) C195 0.031(2) 0.032(3) 0.062(3) -0.002(3) 0.001(2) -0.011(2) C205 0.082(5) 0.056(4) 0.082(5) 0.020(4) -0.017(4) 0.001(4) N16 0.031(3) 0.056(3) 0.059(3) -0.019(2) -0.006(2) 0.003(2) O16 0.037(2) 0.129(5) 0.079(3) -0.026(3) 0.006(2) -0.009(3) O26 0.055(3) 0.086(4) 0.053(2) -0.024(3) 0.016(2) 0.000(3) C16 0.032(3) 0.065(3) 0.056(3) -0.027(2) 0.013(2) -0.009(2) C26 0.052(4) 0.053(3) 0.072(4) -0.020(2) 0.012(3) -0.009(2) C36 0.054(3) 0.052(3) 0.092(4) -0.030(3) 0.024(3) -0.007(3) C46 0.060(4) 0.068(4) 0.118(5) -0.043(3) 0.019(3) -0.021(3) C56 0.040(3) 0.078(3) 0.095(4) -0.061(3) 0.017(3) -0.011(3) C66 0.032(3) 0.082(3) 0.069(3) -0.044(3) 0.013(2) -0.010(3) C76 0.027(3) 0.098(4) 0.068(4) -0.042(3) -0.002(3) 0.006(3) C86 0.033(4) 0.139(4) 0.080(5) -0.040(4) -0.012(3) 0.009(4) C96 0.053(4) 0.150(5) 0.075(5) -0.031(4) -0.016(3) 0.030(4) C106 0.073(5) 0.124(5) 0.053(4) -0.009(4) -0.014(3) 0.023(4) C116 0.059(4) 0.083(3) 0.058(4) -0.016(3) -0.012(3) 0.019(3) C126 0.027(3) 0.078(3) 0.043(3) -0.027(2) 0.003(2) 0.012(2) C136 0.029(2) 0.043(3) 0.047(3) -0.006(3) -0.0045(19) 0.003(2) C146 0.029(2) 0.064(4) 0.032(3) 0.005(3) -0.0108(19) 0.003(3) C156 0.048(3) 0.036(3) 0.036(3) 0.004(2) -0.003(2) -0.009(3) C166 0.038(3) 0.057(4) 0.058(3) 0.005(3) -0.006(3) -0.020(3) C176 0.039(3) 0.089(5) 0.059(3) -0.002(3) 0.009(3) -0.014(3) C186 0.039(3) 0.100(5) 0.054(4) -0.021(4) 0.007(3) -0.007(4) C196 0.040(2) 0.082(5) 0.053(3) -0.016(4) 0.003(2) -0.003(4) C206 0.077(5) 0.121(6) 0.073(4) -0.023(5) 0.037(4) -0.009(5) N17 0.052(3) 0.070(3) 0.045(3) 0.004(2) -0.001(2) -0.018(2) O17 0.053(3) 0.123(4) 0.069(3) -0.025(3) 0.017(3) -0.020(3) O27 0.067(3) 0.102(4) 0.063(3) -0.023(3) 0.017(2) -0.013(4) C17 0.035(3) 0.076(3) 0.039(3) -0.007(2) 0.011(2) -0.001(3) C27 0.051(4) 0.077(3) 0.047(4) -0.003(3) 0.001(3) 0.005(3) C37 0.072(5) 0.086(4) 0.075(5) -0.004(4) -0.021(3) 0.016(3) C47 0.065(4) 0.097(4) 0.071(4) -0.025(3) -0.019(4) 0.021(3) C57 0.044(4) 0.092(4) 0.057(4) -0.035(3) -0.001(3) 0.015(3) C67 0.016(3) 0.080(3) 0.066(4) -0.016(3) 0.010(2) 0.008(2) C77 0.035(3) 0.073(3) 0.053(3) -0.020(3) 0.016(2) -0.007(3) C87 0.042(4) 0.077(3) 0.079(4) -0.031(3) 0.023(3) -0.015(3) C97 0.072(5) 0.071(4) 0.089(5) -0.012(3) 0.030(3) -0.033(4) C107 0.094(5) 0.067(4) 0.073(5) 0.002(4) 0.014(4) -0.020(4) C117 0.070(4) 0.065(3) 0.050(4) -0.005(3) 0.008(3) -0.013(3) C127 0.059(4) 0.060(3) 0.039(3) -0.013(2) 0.008(2) -0.015(3) C137 0.045(3) 0.043(3) 0.039(3) 0.008(2) -0.002(2) -0.004(2) C147 0.044(2) 0.015(3) 0.054(3) 0.000(2) 0.001(2) 0.005(2) C157 0.055(3) 0.052(4) 0.051(3) 0.000(3) -0.008(3) -0.008(3) C167 0.049(3) 0.033(3) 0.076(4) -0.006(3) -0.004(3) -0.013(3) C177 0.044(3) 0.049(4) 0.072(4) -0.001(3) 0.002(3) -0.007(3) C187 0.044(3) 0.059(4) 0.046(3) -0.004(3) 0.000(2) -0.001(3) C197 0.064(3) 0.049(4) 0.062(3) -0.011(3) 0.019(2) -0.026(3) C207 0.089(5) 0.119(6) 0.070(4) -0.006(5) 0.039(4) -0.012(5) N18 0.033(2) 0.037(2) 0.035(3) -0.0087(18) 0.0091(19) -0.0039(18) O18 0.024(2) 0.123(4) 0.077(3) -0.019(3) 0.016(2) -0.016(3) O28 0.044(3) 0.092(4) 0.041(2) -0.012(3) -0.0047(18) -0.003(3) C18 0.033(3) 0.042(2) 0.039(3) -0.015(2) 0.013(2) -0.010(2) C28 0.057(4) 0.049(3) 0.048(3) -0.005(2) 0.010(3) -0.004(3) C38 0.073(4) 0.075(4) 0.040(3) 0.012(3) 0.010(3) -0.001(3) C48 0.067(4) 0.103(4) 0.055(4) 0.004(3) 0.033(4) 0.001(3) C58 0.047(4) 0.089(4) 0.043(4) -0.013(3) 0.018(3) 0.014(3) C68 0.040(3) 0.054(3) 0.024(3) -0.025(2) 0.003(2) 0.000(2) C78 0.032(3) 0.046(2) 0.048(3) -0.020(2) -0.005(2) -0.004(2) C88 0.061(4) 0.051(3) 0.058(4) -0.023(3) 0.002(3) 0.009(3) C98 0.069(4) 0.037(3) 0.074(4) -0.017(3) -0.006(3) 0.003(3) C108 0.058(4) 0.036(3) 0.070(4) -0.006(3) -0.008(3) -0.005(3) C118 0.045(4) 0.043(3) 0.055(3) -0.001(2) -0.004(3) -0.002(2) C128 0.018(2) 0.040(2) 0.048(3) -0.007(2) -0.0111(19) -0.0054(19) C138 0.025(2) 0.043(3) 0.043(3) -0.006(2) 0.0048(18) -0.001(2) C148 0.029(2) 0.074(4) 0.032(3) -0.007(3) 0.008(2) 0.004(3) C158 0.035(3) 0.072(5) 0.058(4) -0.023(3) 0.010(3) 0.003(3) C168 0.023(2) 0.085(5) 0.066(4) -0.008(3) 0.019(3) 0.003(3) C178 0.028(3) 0.082(5) 0.066(4) -0.003(3) -0.014(3) 0.008(3) C188 0.040(3) 0.061(4) 0.061(4) -0.015(3) -0.014(3) 0.005(3) C198 0.0238(19) 0.070(4) 0.045(2) -0.011(3) 0.0081(17) -0.018(3) C208 0.061(4) 0.101(5) 0.062(4) -0.024(4) -0.025(3) -0.014(4) _refine_ls_extinction_method None #_oxford_refine_ls_scale 0.9045(10) #loop_ # _oxford_twin_element_scale_factors # 0.4992(17) # 0.5008(17) 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 N11 . C121 . 1.392(6) yes N11 . C11 . 1.488(10) yes N11 . C131 . 1.367(10) yes O11 . C191 . 1.115(10) yes O21 . C191 . 1.394(10) yes O21 . C201 . 1.472(12) yes C121 . C111 . 1.387(6) yes C121 . C71 . 1.427(9) yes C111 . C101 . 1.380(6) yes C111 . H1111 . 0.950 no C101 . C91 . 1.385(6) yes C101 . H1011 . 0.950 no C91 . C81 . 1.361(6) yes C91 . H911 . 0.950 no C81 . C71 . 1.368(10) yes C81 . H811 . 0.950 no C71 . C61 . 1.463(10) yes C61 . C51 . 1.499(12) yes C61 . C11 . 1.316(12) yes C51 . C41 . 1.347(15) yes C51 . H511 . 0.950 no C41 . C31 . 1.336(15) yes C41 . H411 . 0.950 no C31 . C21 . 1.314(13) yes C31 . H311 . 0.950 no C21 . C11 . 1.358(12) yes C21 . H211 . 0.950 no C131 . C141 . 1.417(11) yes C131 . C181 . 1.455(13) yes C141 . C151 . 1.394(12) yes C141 . C191 . 1.460(12) yes C151 . C161 . 1.313(13) yes C151 . H1511 . 0.950 no C161 . C171 . 1.387(15) yes C161 . H1611 . 0.950 no C171 . C181 . 1.403(15) yes C171 . H1711 . 0.950 no C181 . H1811 . 0.950 no C201 . H2011 . 0.981 no C201 . H2012 . 0.982 no C201 . H2013 . 0.983 no N12 . C12 . 1.391(6) yes N12 . C122 . 1.460(11) yes N12 . C132 . 1.351(10) yes O12 . C192 . 1.238(10) yes O22 . C192 . 1.273(10) yes O22 . C202 . 1.448(11) yes C12 . C22 . 1.375(7) yes C12 . C62 . 1.420(9) yes C22 . C32 . 1.374(6) yes C22 . H221 . 0.950 no C32 . C42 . 1.383(7) yes C32 . H321 . 0.950 no C42 . C52 . 1.377(7) yes C42 . H421 . 0.950 no C52 . C62 . 1.369(10) yes C52 . H521 . 0.950 no C62 . C72 . 1.359(12) yes C72 . C82 . 1.468(14) yes C72 . C122 . 1.423(12) yes C82 . C92 . 1.378(14) yes C82 . H821 . 0.950 no C92 . C102 . 1.338(12) yes C92 . H921 . 0.950 no C102 . C112 . 1.386(12) yes C102 . H1021 . 0.950 no C112 . C122 . 1.382(12) yes C112 . H1121 . 0.950 no C132 . C142 . 1.384(11) yes C132 . C182 . 1.446(11) yes C142 . C152 . 1.361(11) yes C142 . C192 . 1.525(11) yes C152 . C162 . 1.286(12) yes C152 . H1521 . 0.950 no C162 . C172 . 1.376(12) yes C162 . H1621 . 0.950 no C172 . C182 . 1.416(13) yes C172 . H1721 . 0.950 no C182 . H1821 . 0.950 no C202 . H2021 . 0.980 no C202 . H2022 . 0.982 no C202 . H2023 . 0.982 no N13 . C13 . 1.392(6) yes N13 . C123 . 1.383(10) yes N13 . C133 . 1.441(9) yes O13 . C193 . 1.204(11) yes O23 . C193 . 1.313(10) yes O23 . C203 . 1.449(11) yes C13 . C23 . 1.383(6) yes C13 . C63 . 1.428(8) yes C23 . C33 . 1.373(5) yes C23 . H231 . 0.950 no C33 . C43 . 1.393(6) yes C33 . H331 . 0.950 no C43 . C53 . 1.365(6) yes C43 . H431 . 0.950 no C53 . C63 . 1.373(9) yes C53 . H531 . 0.950 no C63 . C73 . 1.406(9) yes C73 . C83 . 1.401(12) yes C73 . C123 . 1.418(11) yes C83 . C93 . 1.387(14) yes C83 . H831 . 0.950 no C93 . C103 . 1.330(13) yes C93 . H931 . 0.950 no C103 . C113 . 1.432(12) yes C103 . H1031 . 0.950 no C113 . C123 . 1.377(11) yes C113 . H1131 . 0.950 no C133 . C143 . 1.343(11) yes C133 . C183 . 1.449(11) yes C143 . C153 . 1.441(11) yes C143 . C193 . 1.475(12) yes C153 . C163 . 1.311(14) yes C153 . H1531 . 0.950 no C163 . C173 . 1.429(14) yes C163 . H1631 . 0.950 no C173 . C183 . 1.357(13) yes C173 . H1731 . 0.950 no C183 . H1831 . 0.950 no C203 . H2031 . 0.984 no C203 . H2032 . 0.984 no C203 . H2033 . 0.979 no N14 . C124 . 1.389(6) yes N14 . C14 . 1.312(10) yes N14 . C134 . 1.471(10) yes O14 . C194 . 1.254(10) yes O24 . C194 . 1.295(10) yes O24 . C204 . 1.419(12) yes C124 . C114 . 1.385(6) yes C124 . C74 . 1.373(9) yes C114 . C104 . 1.387(6) yes C114 . H1141 . 0.950 no C104 . C94 . 1.394(6) yes C104 . H1041 . 0.950 no C94 . C84 . 1.368(7) yes C94 . H941 . 0.950 no C84 . C74 . 1.440(10) yes C84 . H841 . 0.950 no C74 . C64 . 1.413(10) yes C64 . C54 . 1.307(12) yes C64 . C14 . 1.494(12) yes C54 . C44 . 1.387(16) yes C54 . H541 . 0.950 no C44 . C34 . 1.453(16) yes C44 . H441 . 0.950 no C34 . C24 . 1.418(13) yes C34 . H341 . 0.950 no C24 . C14 . 1.404(12) yes C24 . H241 . 0.950 no C134 . C144 . 1.352(12) yes C134 . C184 . 1.341(13) yes C144 . C154 . 1.390(11) yes C144 . C194 . 1.538(12) yes C154 . C164 . 1.446(14) yes C154 . H1541 . 0.950 no C164 . C174 . 1.362(14) yes C164 . H1641 . 0.950 no C174 . C184 . 1.364(13) yes C174 . H1741 . 0.950 no C184 . H1841 . 0.950 no C204 . H2041 . 0.981 no C204 . H2042 . 0.983 no C204 . H2043 . 0.980 no N15 . C15 . 1.391(6) yes N15 . C125 . 1.412(11) yes N15 . C135 . 1.398(11) yes O15 . C195 . 1.181(10) yes O25 . C195 . 1.343(10) yes O25 . C205 . 1.459(12) yes C15 . C25 . 1.377(6) yes C15 . C65 . 1.383(9) yes C25 . C35 . 1.382(6) yes C25 . H251 . 0.950 no C35 . C45 . 1.388(6) yes C35 . H351 . 0.950 no C45 . C55 . 1.369(7) yes C45 . H451 . 0.950 no C55 . C65 . 1.424(10) yes C55 . H551 . 0.950 no C65 . C75 . 1.453(11) yes C75 . C85 . 1.385(13) yes C75 . C125 . 1.401(13) yes C85 . C95 . 1.314(16) yes C85 . H851 . 0.950 no C95 . C105 . 1.492(16) yes C95 . H951 . 0.950 no C105 . C115 . 1.331(13) yes C105 . H1051 . 0.950 no C115 . C125 . 1.369(14) yes C115 . H1151 . 0.950 no C135 . C145 . 1.452(12) yes C135 . C185 . 1.301(13) yes C145 . C155 . 1.330(12) yes C145 . C195 . 1.517(12) yes C155 . C165 . 1.429(13) yes C155 . H1551 . 0.950 no C165 . C175 . 1.337(13) yes C165 . H1651 . 0.950 no C175 . C185 . 1.401(13) yes C175 . H1751 . 0.950 no C185 . H1851 . 0.950 no C205 . H2051 . 0.985 no C205 . H2052 . 0.982 no C205 . H2053 . 0.983 no N16 . C16 . 1.392(6) yes N16 . C126 . 1.315(10) yes N16 . C136 . 1.484(10) yes O16 . C196 . 1.149(11) yes O26 . C196 . 1.378(11) yes O26 . C206 . 1.454(12) yes C16 . C26 . 1.392(6) yes C16 . C66 . 1.389(8) yes C26 . C36 . 1.389(6) yes C26 . H261 . 0.950 no C36 . C46 . 1.376(6) yes C36 . H361 . 0.950 no C46 . C56 . 1.351(7) yes C46 . H461 . 0.950 no C56 . C66 . 1.416(9) yes C56 . H561 . 0.950 no C66 . C76 . 1.517(13) yes C76 . C86 . 1.356(14) yes C76 . C126 . 1.391(13) yes C86 . C96 . 1.356(16) yes C86 . H861 . 0.950 no C96 . C106 . 1.410(14) yes C96 . H961 . 0.950 no C106 . C116 . 1.382(14) yes C106 . H1061 . 0.950 no C116 . C126 . 1.342(13) yes C116 . H1161 . 0.950 no C136 . C146 . 1.439(11) yes C136 . C186 . 1.316(12) yes C146 . C156 . 1.421(10) yes C146 . C196 . 1.441(12) yes C156 . C166 . 1.448(11) yes C156 . H1561 . 0.950 no C166 . C176 . 1.375(12) yes C166 . H1661 . 0.950 no C176 . C186 . 1.318(14) yes C176 . H1761 . 0.950 no C186 . H1861 . 0.950 no C206 . H2061 . 0.983 no C206 . H2062 . 0.979 no C206 . H2063 . 0.979 no N17 . C17 . 1.387(6) yes N17 . C127 . 1.376(10) yes N17 . C137 . 1.440(10) yes O17 . C197 . 1.135(11) yes O27 . C197 . 1.387(11) yes O27 . C207 . 1.486(13) yes C17 . C27 . 1.378(6) yes C17 . C67 . 1.449(9) yes C27 . C37 . 1.377(6) yes C27 . H271 . 0.950 no C37 . C47 . 1.385(6) yes C37 . H371 . 0.950 no C47 . C57 . 1.364(7) yes C47 . H471 . 0.950 no C57 . C67 . 1.345(9) yes C57 . H571 . 0.950 no C67 . C77 . 1.487(11) yes C77 . C87 . 1.345(13) yes C77 . C127 . 1.389(12) yes C87 . C97 . 1.340(15) yes C87 . H871 . 0.950 no C97 . C107 . 1.459(16) yes C97 . H971 . 0.950 no C107 . C117 . 1.343(14) yes C107 . H1071 . 0.950 no C117 . C127 . 1.488(13) yes C117 . H1171 . 0.950 no C137 . C147 . 1.393(10) yes C137 . C187 . 1.462(12) yes C147 . C157 . 1.358(12) yes C147 . C197 . 1.449(12) yes C157 . C167 . 1.401(13) yes C157 . H1571 . 0.950 no C167 . C177 . 1.341(13) yes C167 . H1671 . 0.950 no C177 . C187 . 1.366(12) yes C177 . H1771 . 0.950 no C187 . H1871 . 0.950 no C207 . H2071 . 0.980 no C207 . H2072 . 0.980 no C207 . H2073 . 0.981 no N18 . C18 . 1.376(5) yes N18 . C128 . 1.400(9) yes N18 . C138 . 1.443(9) yes O18 . C198 . 1.244(10) yes O28 . C198 . 1.278(10) yes O28 . C208 . 1.398(11) yes C18 . C28 . 1.381(6) yes C18 . C68 . 1.357(8) yes C28 . C38 . 1.372(6) yes C28 . H281 . 0.950 no C38 . C48 . 1.391(6) yes C38 . H381 . 0.950 no C48 . C58 . 1.369(7) yes C48 . H481 . 0.950 no C58 . C68 . 1.439(8) yes C58 . H581 . 0.950 no C68 . C78 . 1.407(10) yes C78 . C88 . 1.439(12) yes C78 . C128 . 1.378(11) yes C88 . C98 . 1.410(12) yes C88 . H881 . 0.950 no C98 . C108 . 1.331(13) yes C98 . H981 . 0.950 no C108 . C118 . 1.397(12) yes C108 . H1081 . 0.950 no C118 . C128 . 1.310(11) yes C118 . H1181 . 0.950 no C138 . C148 . 1.382(10) yes C138 . C188 . 1.277(11) yes C148 . C158 . 1.445(11) yes C148 . C198 . 1.520(11) yes C158 . C168 . 1.343(13) yes C158 . H1581 . 0.950 no C168 . C178 . 1.413(13) yes C168 . H1681 . 0.950 no C178 . C188 . 1.398(12) yes C178 . H1781 . 0.950 no C188 . H1881 . 0.950 no C208 . H2081 . 0.981 no C208 . H2082 . 0.981 no C208 . H2083 . 0.982 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 C121 . N11 . C11 . 106.6(4) yes C121 . N11 . C131 . 126.6(4) yes C11 . N11 . C131 . 126.4(6) yes C191 . O21 . C201 . 114.0(8) yes N11 . C121 . C111 . 129.37(9) yes N11 . C121 . C71 . 109.4(3) yes C111 . C121 . C71 . 121.1(3) yes C121 . C111 . C101 . 117.56(9) yes C121 . C111 . H1111 . 121.0 no C101 . C111 . H1111 . 121.5 no C111 . C101 . C91 . 121.14(9) yes C111 . C101 . H1011 . 119.2 no C91 . C101 . H1011 . 119.7 no C101 . C91 . C81 . 121.34(9) yes C101 . C91 . H911 . 119.1 no C81 . C91 . H911 . 119.6 no C91 . C81 . C71 . 119.8(3) yes C91 . C81 . H811 . 120.0 no C71 . C81 . H811 . 120.2 no C121 . C71 . C81 . 119.06(9) yes C121 . C71 . C61 . 104.8(6) yes C81 . C71 . C61 . 136.1(6) yes C71 . C61 . C51 . 130.0(8) yes C71 . C61 . C11 . 111.3(7) yes C51 . C61 . C11 . 118.7(8) yes C61 . C51 . C41 . 111.5(8) yes C61 . C51 . H511 . 123.9 no C41 . C51 . H511 . 124.6 no C51 . C41 . C31 . 124.9(9) yes C51 . C41 . H411 . 117.0 no C31 . C41 . H411 . 118.1 no C41 . C31 . C21 . 124.6(10) yes C41 . C31 . H311 . 117.7 no C21 . C31 . H311 . 117.7 no C31 . C21 . C11 . 113.8(9) yes C31 . C21 . H211 . 123.2 no C11 . C21 . H211 . 123.0 no N11 . C11 . C21 . 125.5(7) yes N11 . C11 . C61 . 107.8(6) yes C21 . C11 . C61 . 126.6(8) yes N11 . C131 . C141 . 125.6(8) yes N11 . C131 . C181 . 115.8(7) yes C141 . C131 . C181 . 118.5(8) yes C131 . C141 . C151 . 117.5(8) yes C131 . C141 . C191 . 114.7(7) yes C151 . C141 . C191 . 127.8(7) yes C141 . C151 . C161 . 125.8(9) yes C141 . C151 . H1511 . 117.3 no C161 . C151 . H1511 . 116.8 no C151 . C161 . C171 . 118.0(9) yes C151 . C161 . H1611 . 121.4 no C171 . C161 . H1611 . 120.5 no C161 . C171 . C181 . 122.4(9) yes C161 . C171 . H1711 . 119.3 no C181 . C171 . H1711 . 118.3 no C131 . C181 . C171 . 117.7(9) yes C131 . C181 . H1811 . 120.3 no C171 . C181 . H1811 . 122.0 no C141 . C191 . O21 . 104.5(7) yes C141 . C191 . O11 . 134.2(8) yes O21 . C191 . O11 . 121.3(8) yes O21 . C201 . H2011 . 108.1 no O21 . C201 . H2012 . 108.6 no H2011 . C201 . H2012 . 111.8 no O21 . C201 . H2013 . 108.9 no H2011 . C201 . H2013 . 110.0 no H2012 . C201 . H2013 . 109.4 no C12 . N12 . C122 . 107.2(5) yes C12 . N12 . C132 . 131.2(4) yes C122 . N12 . C132 . 121.6(6) yes C192 . O22 . C202 . 115.9(7) yes N12 . C12 . C22 . 129.34(9) yes N12 . C12 . C62 . 108.5(3) yes C22 . C12 . C62 . 121.9(3) yes C12 . C22 . C32 . 117.56(9) yes C12 . C22 . H221 . 121.4 no C32 . C22 . H221 . 121.1 no C22 . C32 . C42 . 121.15(9) yes C22 . C32 . H321 . 119.6 no C42 . C32 . H321 . 119.3 no C32 . C42 . C52 . 121.36(9) yes C32 . C42 . H421 . 119.5 no C52 . C42 . H421 . 119.1 no C42 . C52 . C62 . 119.0(3) yes C42 . C52 . H521 . 120.6 no C62 . C52 . H521 . 120.3 no C12 . C62 . C52 . 119.02(9) yes C12 . C62 . C72 . 108.7(7) yes C52 . C62 . C72 . 132.2(7) yes C62 . C72 . C82 . 136.7(8) yes C62 . C72 . C122 . 109.7(8) yes C82 . C72 . C122 . 113.5(9) yes C72 . C82 . C92 . 118.7(8) yes C72 . C82 . H821 . 120.8 no C92 . C82 . H821 . 120.5 no C82 . C92 . C102 . 126.2(9) yes C82 . C92 . H921 . 116.7 no C102 . C92 . H921 . 117.1 no C92 . C102 . C112 . 117.2(9) yes C92 . C102 . H1021 . 121.1 no C112 . C102 . H1021 . 121.6 no C102 . C112 . C122 . 120.4(8) yes C102 . C112 . H1121 . 119.5 no C122 . C112 . H1121 . 120.1 no N12 . C122 . C72 . 105.8(8) yes N12 . C122 . C112 . 130.3(7) yes C72 . C122 . C112 . 124.0(9) yes N12 . C132 . C142 . 128.0(7) yes N12 . C132 . C182 . 116.7(7) yes C142 . C132 . C182 . 115.3(7) yes C132 . C142 . C152 . 122.7(7) yes C132 . C142 . C192 . 117.0(6) yes C152 . C142 . C192 . 120.3(7) yes C142 . C152 . C162 . 122.8(8) yes C142 . C152 . H1521 . 118.8 no C162 . C152 . H1521 . 118.4 no C152 . C162 . C172 . 120.2(9) yes C152 . C162 . H1621 . 120.1 no C172 . C162 . H1621 . 119.7 no C162 . C172 . C182 . 120.3(8) yes C162 . C172 . H1721 . 119.4 no C182 . C172 . H1721 . 120.3 no C132 . C182 . C172 . 118.7(8) yes C132 . C182 . H1821 . 120.9 no C172 . C182 . H1821 . 120.4 no C142 . C192 . O22 . 112.7(7) yes C142 . C192 . O12 . 123.3(7) yes O22 . C192 . O12 . 123.8(8) yes O22 . C202 . H2021 . 108.1 no O22 . C202 . H2022 . 109.1 no H2021 . C202 . H2022 . 110.5 no O22 . C202 . H2023 . 108.1 no H2021 . C202 . H2023 . 110.3 no H2022 . C202 . H2023 . 110.6 no C13 . N13 . C123 . 107.5(4) yes C13 . N13 . C133 . 124.5(4) yes C123 . N13 . C133 . 127.7(5) yes C193 . O23 . C203 . 120.7(8) yes N13 . C13 . C23 . 129.34(9) yes N13 . C13 . C63 . 109.3(3) yes C23 . C13 . C63 . 121.3(3) yes C13 . C23 . C33 . 117.63(9) yes C13 . C23 . H231 . 121.4 no C33 . C23 . H231 . 121.0 no C23 . C33 . C43 . 121.22(9) yes C23 . C33 . H331 . 119.6 no C43 . C33 . H331 . 119.2 no C33 . C43 . C53 . 121.34(9) yes C33 . C43 . H431 . 119.5 no C53 . C43 . H431 . 119.1 no C43 . C53 . C63 . 119.4(3) yes C43 . C53 . H531 . 120.5 no C63 . C53 . H531 . 120.1 no C13 . C63 . C53 . 119.05(9) yes C13 . C63 . C73 . 106.2(6) yes C53 . C63 . C73 . 134.4(6) yes C63 . C73 . C83 . 136.4(8) yes C63 . C73 . C123 . 107.8(7) yes C83 . C73 . C123 . 115.8(8) yes C73 . C83 . C93 . 119.5(8) yes C73 . C83 . H831 . 120.4 no C93 . C83 . H831 . 120.1 no C83 . C93 . C103 . 122.9(8) yes C83 . C93 . H931 . 118.5 no C103 . C93 . H931 . 118.7 no C93 . C103 . C113 . 121.7(9) yes C93 . C103 . H1031 . 118.9 no C113 . C103 . H1031 . 119.4 no C103 . C113 . C123 . 114.4(7) yes C103 . C113 . H1131 . 122.9 no C123 . C113 . H1131 . 122.7 no C73 . C123 . N13 . 109.1(6) yes C73 . C123 . C113 . 125.7(7) yes N13 . C123 . C113 . 125.2(7) yes N13 . C133 . C143 . 121.3(7) yes N13 . C133 . C183 . 116.9(7) yes C143 . C133 . C183 . 121.8(7) yes C133 . C143 . C153 . 118.7(7) yes C133 . C143 . C193 . 123.2(7) yes C153 . C143 . C193 . 118.0(7) yes C143 . C153 . C163 . 121.7(8) yes C143 . C153 . H1531 . 119.1 no C163 . C153 . H1531 . 119.3 no C153 . C163 . C173 . 118.5(9) yes C153 . C163 . H1631 . 120.2 no C173 . C163 . H1631 . 121.2 no C163 . C173 . C183 . 123.3(9) yes C163 . C173 . H1731 . 118.0 no C183 . C173 . H1731 . 118.7 no C133 . C183 . C173 . 116.0(8) yes C133 . C183 . H1831 . 122.2 no C173 . C183 . H1831 . 121.8 no C143 . C193 . O23 . 113.5(8) yes C143 . C193 . O13 . 125.8(8) yes O23 . C193 . O13 . 120.8(9) yes O23 . C203 . H2031 . 108.2 no O23 . C203 . H2032 . 108.6 no H2031 . C203 . H2032 . 108.9 no O23 . C203 . H2033 . 110.0 no H2031 . C203 . H2033 . 110.4 no H2032 . C203 . H2033 . 110.7 no C124 . N14 . C14 . 110.9(5) yes C124 . N14 . C134 . 126.1(4) yes C14 . N14 . C134 . 122.5(6) yes C194 . O24 . C204 . 119.3(7) yes N14 . C124 . C114 . 129.37(9) yes N14 . C124 . C74 . 107.8(3) yes C114 . C124 . C74 . 122.8(3) yes C124 . C114 . C104 . 117.56(9) yes C124 . C114 . H1141 . 121.4 no C104 . C114 . H1141 . 121.0 no C114 . C104 . C94 . 121.17(9) yes C114 . C104 . H1041 . 119.6 no C94 . C104 . H1041 . 119.2 no C104 . C94 . C84 . 121.35(9) yes C104 . C94 . H941 . 119.6 no C84 . C94 . H941 . 119.1 no C94 . C84 . C74 . 118.0(3) yes C94 . C84 . H841 . 120.9 no C74 . C84 . H841 . 121.0 no C84 . C74 . C124 . 119.05(9) yes C84 . C74 . C64 . 131.2(6) yes C124 . C74 . C64 . 109.7(6) yes C74 . C64 . C54 . 138.8(9) yes C74 . C64 . C14 . 103.3(7) yes C54 . C64 . C14 . 117.9(9) yes C64 . C54 . C44 . 127.3(10) yes C64 . C54 . H541 . 116.5 no C44 . C54 . H541 . 116.2 no C54 . C44 . C34 . 115.9(9) yes C54 . C44 . H441 . 122.5 no C34 . C44 . H441 . 121.5 no C44 . C34 . C24 . 120.3(9) yes C44 . C34 . H341 . 120.1 no C24 . C34 . H341 . 119.7 no C34 . C24 . C14 . 120.2(9) yes C34 . C24 . H241 . 119.7 no C14 . C24 . H241 . 120.1 no C64 . C14 . C24 . 118.3(7) yes C64 . C14 . N14 . 108.2(7) yes C24 . C14 . N14 . 133.4(8) yes N14 . C134 . C144 . 119.1(8) yes N14 . C134 . C184 . 120.2(8) yes C144 . C134 . C184 . 120.5(8) yes C134 . C144 . C154 . 121.3(8) yes C134 . C144 . C194 . 127.3(7) yes C154 . C144 . C194 . 111.2(7) yes C144 . C154 . C164 . 115.7(8) yes C144 . C154 . H1541 . 121.7 no C164 . C154 . H1541 . 122.5 no C154 . C164 . C174 . 121.8(9) yes C154 . C164 . H1641 . 118.6 no C174 . C164 . H1641 . 119.6 no C164 . C174 . C184 . 117.6(9) yes C164 . C174 . H1741 . 120.9 no C184 . C174 . H1741 . 121.5 no C174 . C184 . C134 . 122.9(9) yes C174 . C184 . H1841 . 117.9 no C134 . C184 . H1841 . 119.2 no C144 . C194 . O24 . 116.8(7) yes C144 . C194 . O14 . 120.0(7) yes O24 . C194 . O14 . 123.2(8) yes O24 . C204 . H2041 . 108.9 no O24 . C204 . H2042 . 110.3 no H2041 . C204 . H2042 . 110.1 no O24 . C204 . H2043 . 109.5 no H2041 . C204 . H2043 . 109.1 no H2042 . C204 . H2043 . 108.8 no C15 . N15 . C125 . 109.3(5) yes C15 . N15 . C135 . 127.8(4) yes C125 . N15 . C135 . 123.0(6) yes C195 . O25 . C205 . 113.1(7) yes N15 . C15 . C25 . 129.33(9) yes N15 . C15 . C65 . 108.0(3) yes C25 . C15 . C65 . 122.6(3) yes C15 . C25 . C35 . 117.65(9) yes C15 . C25 . H251 . 120.9 no C35 . C25 . H251 . 121.4 no C25 . C35 . C45 . 121.22(9) yes C25 . C35 . H351 . 119.2 no C45 . C35 . H351 . 119.6 no C35 . C45 . C55 . 121.36(9) yes C35 . C45 . H451 . 119.1 no C55 . C45 . H451 . 119.5 no C45 . C55 . C65 . 118.1(3) yes C45 . C55 . H551 . 120.7 no C65 . C55 . H551 . 121.2 no C55 . C65 . C15 . 119.02(9) yes C55 . C65 . C75 . 132.6(7) yes C15 . C65 . C75 . 108.4(7) yes C65 . C75 . C85 . 131.8(10) yes C65 . C75 . C125 . 106.4(7) yes C85 . C75 . C125 . 121.8(10) yes C75 . C85 . C95 . 120.2(10) yes C75 . C85 . H851 . 119.9 no C95 . C85 . H851 . 120.0 no C85 . C95 . C105 . 118.7(9) yes C85 . C95 . H951 . 120.6 no C105 . C95 . H951 . 120.7 no C95 . C105 . C115 . 119.6(11) yes C95 . C105 . H1051 . 120.3 no C115 . C105 . H1051 . 120.1 no C105 . C115 . C125 . 121.4(10) yes C105 . C115 . H1151 . 118.9 no C125 . C115 . H1151 . 119.7 no N15 . C125 . C75 . 107.9(8) yes N15 . C125 . C115 . 133.7(8) yes C75 . C125 . C115 . 118.3(8) yes N15 . C135 . C145 . 120.8(8) yes N15 . C135 . C185 . 121.2(8) yes C145 . C135 . C185 . 117.8(8) yes C135 . C145 . C155 . 118.9(8) yes C135 . C145 . C195 . 120.5(7) yes C155 . C145 . C195 . 120.6(8) yes C145 . C155 . C165 . 120.1(8) yes C145 . C155 . H1551 . 120.1 no C165 . C155 . H1551 . 119.7 no C155 . C165 . C175 . 121.6(8) yes C155 . C165 . H1651 . 119.7 no C175 . C165 . H1651 . 118.7 no C165 . C175 . C185 . 116.0(8) yes C165 . C175 . H1751 . 122.2 no C185 . C175 . H1751 . 121.8 no C175 . C185 . C135 . 125.6(9) yes C175 . C185 . H1851 . 117.3 no C135 . C185 . H1851 . 117.1 no C145 . C195 . O25 . 109.0(6) yes C145 . C195 . O15 . 123.9(8) yes O25 . C195 . O15 . 126.9(8) yes O25 . C205 . H2051 . 109.4 no O25 . C205 . H2052 . 109.0 no H2051 . C205 . H2052 . 110.5 no O25 . C205 . H2053 . 109.3 no H2051 . C205 . H2053 . 109.1 no H2052 . C205 . H2053 . 109.5 no C16 . N16 . C126 . 109.7(5) yes C16 . N16 . C136 . 122.6(4) yes C126 . N16 . C136 . 127.7(6) yes C196 . O26 . C206 . 116.3(8) yes N16 . C16 . C26 . 129.31(9) yes N16 . C16 . C66 . 109.1(3) yes C26 . C16 . C66 . 121.4(3) yes C16 . C26 . C36 . 117.67(9) yes C16 . C26 . H261 . 121.1 no C36 . C26 . H261 . 121.3 no C26 . C36 . C46 . 121.27(9) yes C26 . C36 . H361 . 119.3 no C46 . C36 . H361 . 119.5 no C36 . C46 . C56 . 121.40(9) yes C36 . C46 . H461 . 119.3 no C56 . C46 . H461 . 119.3 no C46 . C56 . C66 . 119.3(3) yes C46 . C56 . H561 . 120.2 no C66 . C56 . H561 . 120.5 no C56 . C66 . C16 . 119.03(9) yes C56 . C66 . C76 . 135.8(6) yes C16 . C66 . C76 . 105.1(6) yes C66 . C76 . C86 . 134.5(9) yes C66 . C76 . C126 . 103.9(8) yes C86 . C76 . C126 . 121.6(11) yes C76 . C86 . C96 . 120.5(10) yes C76 . C86 . H861 . 119.4 no C96 . C86 . H861 . 120.0 no C86 . C96 . C106 . 116.1(10) yes C86 . C96 . H961 . 122.0 no C106 . C96 . H961 . 121.9 no C96 . C106 . C116 . 124.6(11) yes C96 . C106 . H1061 . 117.8 no C116 . C106 . H1061 . 117.6 no C106 . C116 . C126 . 116.1(9) yes C106 . C116 . H1161 . 122.3 no C126 . C116 . H1161 . 121.6 no C76 . C126 . C116 . 121.0(9) yes C76 . C126 . N16 . 112.1(9) yes C116 . C126 . N16 . 126.9(8) yes N16 . C136 . C146 . 115.3(6) yes N16 . C136 . C186 . 120.6(7) yes C146 . C136 . C186 . 124.1(8) yes C136 . C146 . C156 . 112.7(7) yes C136 . C146 . C196 . 125.3(7) yes C156 . C146 . C196 . 121.9(7) yes C146 . C156 . C166 . 120.8(7) yes C146 . C156 . H1561 . 119.3 no C166 . C156 . H1561 . 119.9 no C156 . C166 . C176 . 119.4(7) yes C156 . C166 . H1661 . 120.0 no C176 . C166 . H1661 . 120.6 no C166 . C176 . C186 . 119.4(8) yes C166 . C176 . H1761 . 120.6 no C186 . C176 . H1761 . 120.0 no C176 . C186 . C136 . 123.5(9) yes C176 . C186 . H1861 . 118.4 no C136 . C186 . H1861 . 118.0 no C146 . C196 . O26 . 110.0(8) yes C146 . C196 . O16 . 127.5(8) yes O26 . C196 . O16 . 122.4(9) yes O26 . C206 . H2061 . 107.9 no O26 . C206 . H2062 . 110.7 no H2061 . C206 . H2062 . 109.0 no O26 . C206 . H2063 . 107.8 no H2061 . C206 . H2063 . 110.5 no H2062 . C206 . H2063 . 110.8 no C17 . N17 . C127 . 107.5(5) yes C17 . N17 . C137 . 122.7(4) yes C127 . N17 . C137 . 129.6(6) yes C197 . O27 . C207 . 113.5(8) yes N17 . C17 . C27 . 129.31(9) yes N17 . C17 . C67 . 110.0(3) yes C27 . C17 . C67 . 120.7(3) yes C17 . C27 . C37 . 117.61(9) yes C17 . C27 . H271 . 121.0 no C37 . C27 . H271 . 121.4 no C27 . C37 . C47 . 121.17(9) yes C27 . C37 . H371 . 119.2 no C47 . C37 . H371 . 119.6 no C37 . C47 . C57 . 121.35(9) yes C37 . C47 . H471 . 119.2 no C57 . C47 . H471 . 119.4 no C47 . C57 . C67 . 120.0(3) yes C47 . C57 . H571 . 119.9 no C67 . C57 . H571 . 120.0 no C17 . C67 . C57 . 119.05(9) yes C17 . C67 . C77 . 104.3(6) yes C57 . C67 . C77 . 136.6(6) yes C67 . C77 . C87 . 133.9(9) yes C67 . C77 . C127 . 106.0(8) yes C87 . C77 . C127 . 120.1(9) yes C77 . C87 . C97 . 120.1(10) yes C77 . C87 . H871 . 120.2 no C97 . C87 . H871 . 119.7 no C87 . C97 . C107 . 121.8(9) yes C87 . C97 . H971 . 119.5 no C107 . C97 . H971 . 118.8 no C97 . C107 . C117 . 121.3(11) yes C97 . C107 . H1071 . 119.9 no C117 . C107 . H1071 . 118.8 no C107 . C117 . C127 . 114.2(10) yes C107 . C117 . H1171 . 123.1 no C127 . C117 . H1171 . 122.7 no C117 . C127 . C77 . 122.5(8) yes C117 . C127 . N17 . 125.2(8) yes C77 . C127 . N17 . 112.1(8) yes N17 . C137 . C147 . 122.8(7) yes N17 . C137 . C187 . 117.0(7) yes C147 . C137 . C187 . 120.2(7) yes C137 . C147 . C157 . 117.4(8) yes C137 . C147 . C197 . 117.8(7) yes C157 . C147 . C197 . 124.8(7) yes C147 . C157 . C167 . 120.5(8) yes C147 . C157 . H1571 . 120.0 no C167 . C157 . H1571 . 119.6 no C157 . C167 . C177 . 124.8(8) yes C157 . C167 . H1671 . 117.4 no C177 . C167 . H1671 . 117.8 no C167 . C177 . C187 . 116.6(9) yes C167 . C177 . H1771 . 121.5 no C187 . C177 . H1771 . 121.9 no C137 . C187 . C177 . 120.5(8) yes C137 . C187 . H1871 . 119.5 no C177 . C187 . H1871 . 119.9 no C147 . C197 . O27 . 107.6(8) yes C147 . C197 . O17 . 130.1(8) yes O27 . C197 . O17 . 121.2(8) yes O27 . C207 . H2071 . 106.7 no O27 . C207 . H2072 . 110.5 no H2071 . C207 . H2072 . 110.4 no O27 . C207 . H2073 . 108.6 no H2071 . C207 . H2073 . 110.5 no H2072 . C207 . H2073 . 110.1 no C18 . N18 . C128 . 109.4(4) yes C18 . N18 . C138 . 127.2(4) yes C128 . N18 . C138 . 123.4(5) yes C198 . O28 . C208 . 118.8(7) yes N18 . C18 . C28 . 129.31(9) yes N18 . C18 . C68 . 107.5(3) yes C28 . C18 . C68 . 123.2(3) yes C18 . C28 . C38 . 117.60(9) yes C18 . C28 . H281 . 121.3 no C38 . C28 . H281 . 121.1 no C28 . C38 . C48 . 121.18(9) yes C28 . C38 . H381 . 119.5 no C48 . C38 . H381 . 119.3 no C38 . C48 . C58 . 121.37(9) yes C38 . C48 . H481 . 119.4 no C58 . C48 . H481 . 119.2 no C48 . C58 . C68 . 117.6(3) yes C48 . C58 . H581 . 121.3 no C68 . C58 . H581 . 121.2 no C58 . C68 . C18 . 119.04(9) yes C58 . C68 . C78 . 132.0(5) yes C18 . C68 . C78 . 109.0(5) yes C68 . C78 . C88 . 134.7(7) yes C68 . C78 . C128 . 107.6(7) yes C88 . C78 . C128 . 117.7(8) yes C78 . C88 . C98 . 117.5(8) yes C78 . C88 . H881 . 120.9 no C98 . C88 . H881 . 121.5 no C88 . C98 . C108 . 120.1(8) yes C88 . C98 . H981 . 119.7 no C108 . C98 . H981 . 120.2 no C98 . C108 . C118 . 122.3(9) yes C98 . C108 . H1081 . 118.4 no C118 . C108 . H1081 . 119.3 no C108 . C118 . C128 . 118.5(8) yes C108 . C118 . H1181 . 120.8 no C128 . C118 . H1181 . 120.7 no N18 . C128 . C78 . 106.6(6) yes N18 . C128 . C118 . 129.5(7) yes C78 . C128 . C118 . 123.9(8) yes N18 . C138 . C148 . 120.0(7) yes N18 . C138 . C188 . 117.7(7) yes C148 . C138 . C188 . 122.3(7) yes C138 . C148 . C158 . 117.8(7) yes C138 . C148 . C198 . 125.4(7) yes C158 . C148 . C198 . 116.8(6) yes C148 . C158 . C168 . 121.8(8) yes C148 . C158 . H1581 . 119.0 no C168 . C158 . H1581 . 119.3 no C158 . C168 . C178 . 115.7(8) yes C158 . C168 . H1681 . 122.3 no C178 . C168 . H1681 . 122.0 no C168 . C178 . C188 . 122.4(8) yes C168 . C178 . H1781 . 118.9 no C188 . C178 . H1781 . 118.7 no C178 . C188 . C138 . 120.1(8) yes C178 . C188 . H1881 . 119.6 no C138 . C188 . H1881 . 120.3 no C148 . C198 . O28 . 115.7(7) yes C148 . C198 . O18 . 121.0(7) yes O28 . C198 . O18 . 122.4(7) yes O28 . C208 . H2081 . 107.6 no O28 . C208 . H2082 . 108.2 no H2081 . C208 . H2082 . 111.0 no O28 . C208 . H2083 . 108.4 no H2081 . C208 . H2083 . 110.6 no H2082 . C208 . H2083 . 111.0 no _chemical_name_common 'Methyl 2-(9H-carbazol-9-yl)benzoate' _exptl_crystal_recrystallization_method ; A mixture of carbazole, methyl 2-iodobenzoate, copper powder, potassium carbonate and nitrobenzene were heated at 175 degrees C for 48 h. After cooling, the resultant mixture was a red solid. A mixture of water/chloroform (1:1) was added to the solid, and the two layers separated. The aqueous layer was then extracted twice with chloroform, and the organic layers were combined and dried over MgSO4. The solvent was removed under reduced pressure, and the residue oil was purified by flash dry chromatography on silica using hexane/ethyl acetate (85:15) as the eluant. This resulted in the formation of colourless crystals. (5.30 g, 88%) ; #edit data_1_5GPa_I.cif _database_code_depnum_ccdc_archive 'CCDC 752556' #_oxford_structure_analysis_title 'mben05 in Pn' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 7.3592(7) _cell_length_b 14.601(2) _cell_length_c 51.188(9) _cell_angle_alpha 90 _cell_angle_beta 89.989(10) _cell_angle_gamma 90 _cell_volume 5500.2(14) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 n 1 ' _symmetry_space_group_name_Hall 'P -2yac' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y,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 0.0000 0.0010 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0010 0.0010 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0030 0.0030 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 16 # Given Formula = C20 H15 N1 O2 # Dc = 1.46 Fooo = 2528.00 Mu = 0.94 M = 2410.76 # Found Formula = C20 H15 N1 O2 # Dc = 1.46 FOOO = 2528.00 Mu = 0.94 M = 2410.76 _chemical_formula_sum 'C20 H15 N1 O2' _chemical_formula_moiety 'C20 H15 N1 O2' _chemical_compound_source ? _chemical_formula_weight 301.34 _cell_measurement_reflns_used 1559 _cell_measurement_theta_min 2 _cell_measurement_theta_max 13 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 2528 _exptl_absorpt_coefficient_mu 0.094 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.82 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device APEX-II _diffrn_measurement_device_type Area _diffrn_radiation_monochromator silicon _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.47620 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 293 _diffrn_ambient_pressure 1500000 _diffrn_reflns_number 17318 _reflns_number_total 4178 _diffrn_reflns_av_R_equivalents 0.1432 # Number of reflections with Friedels Law is 4178 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5657 _diffrn_reflns_reduction_process ; Merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 ; _diffrn_reflns_theta_min 1.076 _diffrn_reflns_theta_max 13.705 _diffrn_measured_fraction_theta_max 0.733 _diffrn_reflns_theta_full 10.279 _diffrn_measured_fraction_theta_full 0.782 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 43 _reflns_limit_h_min -7 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 43 #_oxford_diffrn_Wilson_B_factor 0.73 #_oxford_diffrn_Wilson_scale 1.11 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.34 _refine_diff_density_max 0.36 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement #_oxford_reflns_threshold_expression_ref I>2.0\s(I) _refine_ls_number_reflns 3239 _refine_ls_number_restraints 1154 _refine_ls_number_parameters 738 #_oxford_refine_ls_R_factor_ref 0.0858 _refine_ls_wR_factor_ref 0.0899 _refine_ls_goodness_of_fit_ref 1.0111 _refine_ls_shift/su_max 0.028935 # The values computed from all data #_oxford_reflns_number_all 4138 _refine_ls_R_factor_all 0.1132 _refine_ls_wR_factor_all 0.1309 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3239 _refine_ls_R_factor_gt 0.0858 _refine_ls_wR_factor_gt 0.0899 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 8.66 -4.45 4.72 ; 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens N11 N -0.073(2) 0.6820(8) -0.1387(3) 0.036(2) 1.0000 Uiso D U . . . . . O11 O 0.0945(19) 0.6573(13) -0.0860(4) 0.036(3) 1.0000 Uiso D U . . . . . O21 O -0.1061(18) 0.7156(13) -0.0606(3) 0.037(3) 1.0000 Uiso D U . . . . . C121 C 0.0092(16) 0.7735(8) -0.1354(2) 0.036(2) 1.0000 Uiso D U . . . . . C111 C -0.0372(18) 0.8410(10) -0.1210(3) 0.036(3) 1.0000 Uiso D U . . . . . C101 C 0.051(2) 0.9178(10) -0.1242(3) 0.036(3) 1.0000 Uiso D U . . . . . C91 C 0.187(2) 0.9305(10) -0.1418(3) 0.036(3) 1.0000 Uiso D U . . . . . C81 C 0.2431(18) 0.8640(10) -0.1576(3) 0.036(3) 1.0000 Uiso D U . . . . . C71 C 0.1478(16) 0.7779(8) -0.1541(2) 0.036(3) 1.0000 Uiso D U . . . . . C61 C 0.1624(17) 0.6917(8) -0.1690(2) 0.037(3) 1.0000 Uiso D U . . . . . C51 C 0.2646(19) 0.6593(11) -0.1885(3) 0.038(3) 1.0000 Uiso D U . . . . . C41 C 0.235(2) 0.5735(12) -0.1981(3) 0.038(3) 1.0000 Uiso D U . . . . . C31 C 0.100(2) 0.5183(10) -0.1880(3) 0.038(3) 1.0000 Uiso D U . . . . . C21 C -0.0079(19) 0.5473(10) -0.1680(3) 0.037(3) 1.0000 Uiso D U . . . . . C11 C 0.0209(17) 0.6344(8) -0.1583(2) 0.037(2) 1.0000 Uiso D U . . . . . C131 C -0.2143(15) 0.6497(8) -0.1239(3) 0.035(2) 1.0000 Uiso D U . . . . . C141 C -0.2246(16) 0.6465(9) -0.0966(3) 0.035(2) 1.0000 Uiso D U . . . . . C151 C -0.377(2) 0.6121(9) -0.0848(3) 0.035(3) 1.0000 Uiso D U . . . . . C161 C -0.5219(19) 0.5803(9) -0.0975(4) 0.035(3) 1.0000 Uiso D U . . . . . C171 C -0.5194(19) 0.5824(9) -0.1247(4) 0.035(3) 1.0000 Uiso D U . . . . . C181 C -0.372(2) 0.6161(9) -0.1383(3) 0.035(3) 1.0000 Uiso D U . . . . . C191 C -0.0580(16) 0.6718(15) -0.0828(3) 0.036(3) 1.0000 Uiso D U . . . . . C201 C 0.038(3) 0.747(2) -0.0430(5) 0.038(4) 1.0000 Uiso D U . . . . . N12 N 0.0812(17) 0.2930(8) 0.0023(3) 0.029(2) 1.0000 Uiso D U . . . . . O12 O -0.1189(19) 0.2214(13) -0.0379(3) 0.034(3) 1.0000 Uiso D U . . . . . O22 O 0.0483(17) 0.1792(13) -0.0717(3) 0.032(3) 1.0000 Uiso D U . . . . . C12 C 0.0120(16) 0.3757(8) -0.0059(2) 0.030(2) 1.0000 Uiso D U . . . . . C22 C 0.0727(18) 0.4324(10) -0.0255(3) 0.030(3) 1.0000 Uiso D U . . . . . C32 C -0.019(2) 0.5128(10) -0.0296(3) 0.031(3) 1.0000 Uiso D U . . . . . C42 C -0.167(2) 0.5365(9) -0.0144(3) 0.031(3) 1.0000 Uiso D U . . . . . C52 C -0.2296(17) 0.4799(10) 0.0051(3) 0.031(3) 1.0000 Uiso D U . . . . . C62 C -0.1409(16) 0.3990(8) 0.0098(2) 0.030(2) 1.0000 Uiso D U . . . . . C72 C -0.1680(16) 0.3293(8) 0.0265(2) 0.030(2) 1.0000 Uiso D U . . . . . C82 C -0.2943(18) 0.3086(10) 0.0476(3) 0.031(3) 1.0000 Uiso D U . . . . . C92 C -0.2767(19) 0.2255(11) 0.0606(3) 0.031(3) 1.0000 Uiso D U . . . . . C102 C -0.153(2) 0.1614(10) 0.0555(3) 0.031(3) 1.0000 Uiso D U . . . . . C112 C -0.0290(18) 0.1797(9) 0.0355(3) 0.030(3) 1.0000 Uiso D U . . . . . C122 C -0.0384(15) 0.2594(8) 0.0223(2) 0.029(2) 1.0000 Uiso D U . . . . . C132 C 0.2135(15) 0.2398(8) -0.0091(2) 0.029(2) 1.0000 Uiso D U . . . . . C142 C 0.2060(15) 0.1946(9) -0.0320(2) 0.030(2) 1.0000 Uiso D U . . . . . C152 C 0.351(2) 0.1484(9) -0.0421(3) 0.030(3) 1.0000 Uiso D U . . . . . C162 C 0.5097(19) 0.1449(9) -0.0300(3) 0.029(3) 1.0000 Uiso D U . . . . . C172 C 0.5346(18) 0.1902(10) -0.0065(3) 0.029(3) 1.0000 Uiso D U . . . . . C182 C 0.3839(19) 0.2371(9) 0.0037(3) 0.029(3) 1.0000 Uiso D U . . . . . C192 C 0.0290(16) 0.1987(18) -0.0480(3) 0.031(3) 1.0000 Uiso D U . . . . . C202 C -0.116(3) 0.177(2) -0.0878(4) 0.033(4) 1.0000 Uiso D U . . . . . N13 N 0.555(2) 0.3676(8) 0.1168(3) 0.033(2) 1.0000 Uiso D U . . . . . O13 O 0.3804(19) 0.4120(13) 0.1670(4) 0.037(3) 1.0000 Uiso D U . . . . . O23 O 0.5805(18) 0.3590(12) 0.1954(3) 0.035(3) 1.0000 Uiso D U . . . . . C13 C 0.4879(16) 0.2799(8) 0.1217(2) 0.034(2) 1.0000 Uiso D U . . . . . C23 C 0.5471(18) 0.2148(10) 0.1390(3) 0.034(3) 1.0000 Uiso D U . . . . . C33 C 0.463(2) 0.1311(10) 0.1386(3) 0.035(3) 1.0000 Uiso D U . . . . . C43 C 0.323(2) 0.1127(10) 0.1213(3) 0.035(3) 1.0000 Uiso D U . . . . . C53 C 0.2636(18) 0.1769(10) 0.1041(3) 0.035(3) 1.0000 Uiso D U . . . . . C63 C 0.3418(16) 0.2608(8) 0.1039(2) 0.034(2) 1.0000 Uiso D U . . . . . C73 C 0.3172(16) 0.3405(8) 0.0888(2) 0.034(2) 1.0000 Uiso D U . . . . . C83 C 0.2070(18) 0.3671(10) 0.0682(3) 0.034(3) 1.0000 Uiso D U . . . . . C93 C 0.236(2) 0.4525(11) 0.0561(3) 0.035(3) 1.0000 Uiso D U . . . . . C103 C 0.369(2) 0.5098(10) 0.0640(3) 0.034(3) 1.0000 Uiso D U . . . . . C113 C 0.4869(18) 0.4877(9) 0.0845(3) 0.034(3) 1.0000 Uiso D U . . . . . C123 C 0.4594(16) 0.4041(8) 0.0967(2) 0.033(2) 1.0000 Uiso D U . . . . . C133 C 0.7050(15) 0.4069(8) 0.1302(3) 0.033(2) 1.0000 Uiso D U . . . . . C143 C 0.6965(15) 0.4195(9) 0.1566(3) 0.033(2) 1.0000 Uiso D U . . . . . C153 C 0.852(2) 0.4594(9) 0.1687(3) 0.032(3) 1.0000 Uiso D U . . . . . C163 C 0.9994(19) 0.4848(9) 0.1565(4) 0.032(3) 1.0000 Uiso D U . . . . . C173 C 1.0041(18) 0.4714(9) 0.1283(4) 0.032(3) 1.0000 Uiso D U . . . . . C183 C 0.864(2) 0.4335(9) 0.1152(3) 0.032(3) 1.0000 Uiso D U . . . . . C193 C 0.5411(15) 0.3966(14) 0.1718(3) 0.035(3) 1.0000 Uiso D U . . . . . C203 C 0.433(3) 0.333(2) 0.2122(4) 0.037(4) 1.0000 Uiso D U . . . . . N14 N -0.0696(19) 0.2084(8) 0.2570(3) 0.032(2) 1.0000 Uiso D U . . . . . O14 O 0.1056(19) 0.1727(13) 0.2086(4) 0.038(3) 1.0000 Uiso D U . . . . . O24 O -0.0921(18) 0.2155(13) 0.1765(3) 0.039(3) 1.0000 Uiso D U . . . . . C124 C 0.0050(16) 0.2919(8) 0.2541(2) 0.033(2) 1.0000 Uiso D U . . . . . C114 C -0.0489(18) 0.3657(10) 0.2361(3) 0.033(3) 1.0000 Uiso D U . . . . . C104 C 0.050(2) 0.4498(10) 0.2380(3) 0.034(3) 1.0000 Uiso D U . . . . . C94 C 0.191(2) 0.4596(9) 0.2563(3) 0.033(3) 1.0000 Uiso D U . . . . . C84 C 0.2325(18) 0.3848(10) 0.2725(3) 0.033(3) 1.0000 Uiso D U . . . . . C74 C 0.1493(16) 0.3046(8) 0.2721(2) 0.032(2) 1.0000 Uiso D U . . . . . C64 C 0.1544(16) 0.2203(8) 0.2854(2) 0.032(2) 1.0000 Uiso D U . . . . . C54 C 0.2746(18) 0.1883(10) 0.3060(3) 0.032(3) 1.0000 Uiso D U . . . . . C44 C 0.250(2) 0.1015(11) 0.3152(3) 0.032(3) 1.0000 Uiso D U . . . . . C34 C 0.114(2) 0.0452(10) 0.3054(3) 0.032(3) 1.0000 Uiso D U . . . . . C24 C -0.0024(18) 0.0755(9) 0.2860(3) 0.032(3) 1.0000 Uiso D U . . . . . C14 C 0.0230(16) 0.1632(8) 0.2766(2) 0.032(2) 1.0000 Uiso D U . . . . . C134 C -0.2303(15) 0.1725(8) 0.2426(3) 0.033(2) 1.0000 Uiso D U . . . . . C144 C -0.2116(15) 0.1578(9) 0.2165(3) 0.034(2) 1.0000 Uiso D U . . . . . C154 C -0.359(2) 0.1208(9) 0.2026(3) 0.034(3) 1.0000 Uiso D U . . . . . C164 C -0.5169(19) 0.0986(9) 0.2171(4) 0.034(3) 1.0000 Uiso D U . . . . . C174 C -0.5289(18) 0.1132(9) 0.2431(4) 0.034(3) 1.0000 Uiso D U . . . . . C184 C -0.382(2) 0.1498(9) 0.2558(3) 0.034(3) 1.0000 Uiso D U . . . . . C194 C -0.0486(15) 0.1828(16) 0.1998(3) 0.037(3) 1.0000 Uiso D U . . . . . C204 C 0.057(3) 0.242(2) 0.1609(4) 0.040(4) 1.0000 Uiso D U . . . . . N15 N 0.0419(19) 0.1217(8) 0.5010(3) 0.030(2) 1.0000 Uiso D U . . . . . O15 O -0.1276(19) 0.0958(12) 0.4508(4) 0.032(3) 1.0000 Uiso D U . . . . . O25 O 0.0754(18) 0.1553(13) 0.4226(3) 0.033(3) 1.0000 Uiso D U . . . . . C15 C -0.0412(15) 0.2066(8) 0.4978(2) 0.030(2) 1.0000 Uiso D U . . . . . C25 C 0.0103(17) 0.2795(10) 0.4823(3) 0.030(3) 1.0000 Uiso D U . . . . . C35 C -0.080(2) 0.3607(10) 0.4854(3) 0.031(3) 1.0000 Uiso D U . . . . . C45 C -0.219(2) 0.3694(10) 0.5036(3) 0.031(3) 1.0000 Uiso D U . . . . . C55 C -0.2712(17) 0.2975(10) 0.5188(3) 0.031(3) 1.0000 Uiso D U . . . . . C65 C -0.1784(16) 0.2120(8) 0.5155(2) 0.030(2) 1.0000 Uiso D U . . . . . C75 C -0.1851(16) 0.1259(8) 0.5301(2) 0.030(2) 1.0000 Uiso D U . . . . . C85 C -0.3012(18) 0.0962(10) 0.5499(3) 0.031(3) 1.0000 Uiso D U . . . . . C95 C -0.280(2) 0.0163(11) 0.5599(3) 0.031(3) 1.0000 Uiso D U . . . . . C105 C -0.135(2) -0.0429(9) 0.5503(3) 0.031(3) 1.0000 Uiso D U . . . . . C115 C -0.0227(18) -0.0122(9) 0.5309(3) 0.030(3) 1.0000 Uiso D U . . . . . C125 C -0.0506(16) 0.0724(8) 0.5210(2) 0.030(2) 1.0000 Uiso D U . . . . . C135 C 0.1903(15) 0.0843(8) 0.4865(3) 0.029(2) 1.0000 Uiso D U . . . . . C145 C 0.1909(15) 0.0811(8) 0.4589(3) 0.030(2) 1.0000 Uiso D U . . . . . C155 C 0.336(2) 0.0501(9) 0.4459(3) 0.030(3) 1.0000 Uiso D U . . . . . C165 C 0.4890(18) 0.0204(9) 0.4608(4) 0.030(3) 1.0000 Uiso D U . . . . . C175 C 0.4903(18) 0.0230(9) 0.4862(4) 0.030(3) 1.0000 Uiso D U . . . . . C185 C 0.3352(19) 0.0566(9) 0.4989(3) 0.030(3) 1.0000 Uiso D U . . . . . C195 C 0.0203(15) 0.1115(15) 0.4429(3) 0.031(3) 1.0000 Uiso D U . . . . . C205 C -0.069(3) 0.1896(19) 0.4060(5) 0.034(4) 1.0000 Uiso D U . . . . . N16 N 0.5473(18) 0.2283(8) 0.6043(3) 0.032(2) 1.0000 Uiso D U . . . . . O16 O 0.3714(19) 0.2797(13) 0.6492(3) 0.037(3) 1.0000 Uiso D U . . . . . O26 O 0.5417(18) 0.3068(13) 0.6838(3) 0.036(3) 1.0000 Uiso D U . . . . . C16 C 0.4739(16) 0.1414(8) 0.6090(2) 0.032(2) 1.0000 Uiso D U . . . . . C26 C 0.5232(18) 0.0764(10) 0.6271(3) 0.033(3) 1.0000 Uiso D U . . . . . C36 C 0.428(2) -0.0051(10) 0.6271(3) 0.034(3) 1.0000 Uiso D U . . . . . C46 C 0.2890(19) -0.0212(9) 0.6097(3) 0.033(3) 1.0000 Uiso D U . . . . . C56 C 0.2390(18) 0.0423(10) 0.5920(3) 0.033(3) 1.0000 Uiso D U . . . . . C66 C 0.3319(16) 0.1264(8) 0.5914(2) 0.032(2) 1.0000 Uiso D U . . . . . C76 C 0.3170(16) 0.2135(8) 0.5752(2) 0.032(2) 1.0000 Uiso D U . . . . . C86 C 0.2043(18) 0.2442(10) 0.5560(3) 0.033(3) 1.0000 Uiso D U . . . . . C96 C 0.218(2) 0.3290(12) 0.5465(3) 0.033(3) 1.0000 Uiso D U . . . . . C106 C 0.354(2) 0.3854(10) 0.5577(3) 0.033(3) 1.0000 Uiso D U . . . . . C116 C 0.4724(18) 0.3591(10) 0.5769(3) 0.033(3) 1.0000 Uiso D U . . . . . C126 C 0.4516(16) 0.2702(8) 0.5859(2) 0.032(2) 1.0000 Uiso D U . . . . . C136 C 0.7118(15) 0.2637(8) 0.6174(2) 0.032(2) 1.0000 Uiso D U . . . . . C146 C 0.6820(15) 0.3000(9) 0.6437(2) 0.033(2) 1.0000 Uiso D U . . . . . C156 C 0.8366(19) 0.3443(9) 0.6538(3) 0.032(3) 1.0000 Uiso D U . . . . . C166 C 0.9991(19) 0.3531(9) 0.6390(4) 0.031(3) 1.0000 Uiso D U . . . . . C176 C 1.0062(18) 0.3155(10) 0.6146(3) 0.032(3) 1.0000 Uiso D U . . . . . C186 C 0.8662(19) 0.2719(9) 0.6039(3) 0.032(3) 1.0000 Uiso D U . . . . . C196 C 0.5126(16) 0.2932(18) 0.6570(3) 0.035(3) 1.0000 Uiso D U . . . . . C206 C 0.380(3) 0.301(2) 0.6996(4) 0.037(4) 1.0000 Uiso D U . . . . . N17 N -0.1160(18) 0.1977(8) 0.7479(3) 0.032(2) 1.0000 Uiso D U . . . . . O17 O 0.0635(19) 0.1414(13) 0.7044(3) 0.037(3) 1.0000 Uiso D U . . . . . O27 O -0.1079(18) 0.1044(13) 0.6705(3) 0.037(3) 1.0000 Uiso D U . . . . . C17 C -0.0064(16) 0.1617(8) 0.7676(2) 0.032(2) 1.0000 Uiso D U . . . . . C27 C -0.0215(18) 0.0805(9) 0.7809(3) 0.032(3) 1.0000 Uiso D U . . . . . C37 C 0.101(2) 0.0640(10) 0.8006(3) 0.033(3) 1.0000 Uiso D U . . . . . C47 C 0.2328(19) 0.1271(11) 0.8070(3) 0.033(3) 1.0000 Uiso D U . . . . . C57 C 0.2476(18) 0.2080(10) 0.7940(3) 0.033(3) 1.0000 Uiso D U . . . . . C67 C 0.1324(16) 0.2277(8) 0.7745(2) 0.032(2) 1.0000 Uiso D U . . . . . C77 C 0.1030(16) 0.3047(8) 0.7574(2) 0.032(2) 1.0000 Uiso D U . . . . . C87 C 0.1772(18) 0.3892(10) 0.7542(3) 0.033(3) 1.0000 Uiso D U . . . . . C97 C 0.117(2) 0.4491(9) 0.7366(3) 0.033(3) 1.0000 Uiso D U . . . . . C107 C -0.032(2) 0.4271(10) 0.7197(3) 0.034(3) 1.0000 Uiso D U . . . . . C117 C -0.1186(18) 0.3423(10) 0.7213(3) 0.033(3) 1.0000 Uiso D U . . . . . C127 C -0.0439(16) 0.2831(8) 0.7409(2) 0.032(2) 1.0000 Uiso D U . . . . . C137 C -0.2581(15) 0.1454(8) 0.7352(3) 0.032(2) 1.0000 Uiso D U . . . . . C147 C -0.2486(15) 0.1148(9) 0.7102(3) 0.033(2) 1.0000 Uiso D U . . . . . C157 C -0.4028(19) 0.0727(9) 0.7001(3) 0.032(3) 1.0000 Uiso D U . . . . . C167 C -0.5536(19) 0.0653(9) 0.7146(4) 0.032(3) 1.0000 Uiso D U . . . . . C177 C -0.5673(18) 0.0938(9) 0.7390(4) 0.031(3) 1.0000 Uiso D U . . . . . C187 C -0.4192(19) 0.1365(9) 0.7499(3) 0.031(3) 1.0000 Uiso D U . . . . . C197 C -0.0719(17) 0.1233(19) 0.6959(3) 0.035(3) 1.0000 Uiso D U . . . . . C207 C 0.055(3) 0.115(2) 0.6538(4) 0.039(4) 1.0000 Uiso D U . . . . . N18 N 0.3816(18) 0.2694(8) 0.8610(3) 0.031(2) 1.0000 Uiso D U . . . . . O18 O 0.5748(19) 0.3370(13) 0.9029(3) 0.038(3) 1.0000 Uiso D U . . . . . O28 O 0.4150(18) 0.3863(14) 0.9360(3) 0.038(3) 1.0000 Uiso D U . . . . . C18 C 0.4929(16) 0.3035(8) 0.8417(2) 0.031(2) 1.0000 Uiso D U . . . . . C28 C 0.4811(18) 0.3847(9) 0.8283(3) 0.032(3) 1.0000 Uiso D U . . . . . C38 C 0.606(2) 0.4008(10) 0.8092(3) 0.033(3) 1.0000 Uiso D U . . . . . C48 C 0.7385(19) 0.3362(11) 0.8031(3) 0.033(3) 1.0000 Uiso D U . . . . . C58 C 0.7517(18) 0.2558(10) 0.8164(3) 0.032(3) 1.0000 Uiso D U . . . . . C68 C 0.6214(16) 0.2389(8) 0.8367(2) 0.032(2) 1.0000 Uiso D U . . . . . C78 C 0.5958(16) 0.1641(8) 0.8546(2) 0.031(2) 1.0000 Uiso D U . . . . . C88 C 0.6891(18) 0.0797(10) 0.8589(3) 0.032(3) 1.0000 Uiso D U . . . . . C98 C 0.618(2) 0.0241(9) 0.8788(3) 0.032(3) 1.0000 Uiso D U . . . . . C108 C 0.473(2) 0.0508(10) 0.8929(3) 0.033(3) 1.0000 Uiso D U . . . . . C118 C 0.3868(18) 0.1315(10) 0.8883(3) 0.032(3) 1.0000 Uiso D U . . . . . C128 C 0.4471(16) 0.1871(8) 0.8696(2) 0.031(2) 1.0000 Uiso D U . . . . . C138 C 0.2299(15) 0.3160(8) 0.8727(2) 0.032(2) 1.0000 Uiso D U . . . . . C148 C 0.2558(15) 0.3632(9) 0.8961(3) 0.033(2) 1.0000 Uiso D U . . . . . C158 C 0.112(2) 0.4152(9) 0.9064(3) 0.034(3) 1.0000 Uiso D U . . . . . C168 C -0.0560(19) 0.4203(9) 0.8936(3) 0.034(3) 1.0000 Uiso D U . . . . . C178 C -0.0712(18) 0.3704(10) 0.8698(3) 0.033(3) 1.0000 Uiso D U . . . . . C188 C 0.072(2) 0.3192(9) 0.8601(3) 0.033(3) 1.0000 Uiso D U . . . . . C198 C 0.4256(16) 0.3620(19) 0.9114(3) 0.036(3) 1.0000 Uiso D U . . . . . C208 C 0.571(3) 0.387(2) 0.9516(4) 0.039(4) 1.0000 Uiso D U . . . . . H1111 H -0.1312 0.8352 -0.1083 0.0427 1.0000 Uiso R . . . . . . H1011 H 0.0194 0.9691 -0.1137 0.0426 1.0000 Uiso R . . . . . . H911 H 0.2484 0.9874 -0.1436 0.0430 1.0000 Uiso R . . . . . . H811 H 0.3369 0.8715 -0.1702 0.0430 1.0000 Uiso R . . . . . . H511 H 0.3580 0.6960 -0.1959 0.0446 1.0000 Uiso R . . . . . . H411 H 0.3052 0.5483 -0.2120 0.0451 1.0000 Uiso R . . . . . . H311 H 0.0808 0.4587 -0.1949 0.0445 1.0000 Uiso R . . . . . . H211 H -0.0997 0.5086 -0.1610 0.0432 1.0000 Uiso R . . . . . . H1511 H -0.3800 0.6107 -0.0663 0.0412 1.0000 Uiso R . . . . . . H1611 H -0.6239 0.5566 -0.0884 0.0415 1.0000 Uiso R . . . . . . H1711 H -0.6215 0.5604 -0.1341 0.0415 1.0000 Uiso R . . . . . . H1811 H -0.3729 0.6173 -0.1569 0.0416 1.0000 Uiso R . . . . . . H2011 H -0.0169 0.7773 -0.0278 0.0453 1.0000 Uiso R . . . . . . H2012 H 0.1169 0.7899 -0.0522 0.0453 1.0000 Uiso R . . . . . . H2013 H 0.1094 0.6942 -0.0370 0.0453 1.0000 Uiso R . . . . . . H221 H 0.1747 0.4162 -0.0359 0.0359 1.0000 Uiso R . . . . . . H321 H 0.0195 0.5529 -0.0431 0.0368 1.0000 Uiso R . . . . . . H421 H -0.2273 0.5931 -0.0175 0.0372 1.0000 Uiso R . . . . . . H521 H -0.3326 0.4966 0.0152 0.0368 1.0000 Uiso R . . . . . . H821 H -0.3868 0.3509 0.0524 0.0367 1.0000 Uiso R . . . . . . H921 H -0.3603 0.2134 0.0743 0.0375 1.0000 Uiso R . . . . . . H1021 H -0.1496 0.1057 0.0651 0.0367 1.0000 Uiso R . . . . . . H1121 H 0.0618 0.1359 0.0312 0.0355 1.0000 Uiso R . . . . . . H1521 H 0.3381 0.1177 -0.0583 0.0351 1.0000 Uiso R . . . . . . H1621 H 0.6071 0.1112 -0.0375 0.0347 1.0000 Uiso R . . . . . . H1721 H 0.6483 0.1894 0.0023 0.0348 1.0000 Uiso R . . . . . . H1821 H 0.3971 0.2684 0.0199 0.0347 1.0000 Uiso R . . . . . . H2021 H -0.0835 0.1609 -0.1058 0.0395 1.0000 Uiso R . . . . . . H2022 H -0.1743 0.2374 -0.0876 0.0395 1.0000 Uiso R . . . . . . H2023 H -0.2003 0.1312 -0.0808 0.0395 1.0000 Uiso R . . . . . . H231 H 0.6433 0.2273 0.1509 0.0408 1.0000 Uiso R . . . . . . H331 H 0.5010 0.0849 0.1505 0.0411 1.0000 Uiso R . . . . . . H431 H 0.2682 0.0539 0.1214 0.0414 1.0000 Uiso R . . . . . . H531 H 0.1678 0.1629 0.0924 0.0414 1.0000 Uiso R . . . . . . H831 H 0.1121 0.3282 0.0623 0.0410 1.0000 Uiso R . . . . . . H931 H 0.1605 0.4702 0.0420 0.0416 1.0000 Uiso R . . . . . . H1031 H 0.3834 0.5669 0.0553 0.0409 1.0000 Uiso R . . . . . . H1131 H 0.5809 0.5281 0.0899 0.0400 1.0000 Uiso R . . . . . . H1531 H 0.8487 0.4683 0.1871 0.0386 1.0000 Uiso R . . . . . . H1631 H 1.0994 0.5108 0.1656 0.0382 1.0000 Uiso R . . . . . . H1731 H 1.1090 0.4899 0.1189 0.0382 1.0000 Uiso R . . . . . . H1831 H 0.8684 0.4245 0.0969 0.0383 1.0000 Uiso R . . . . . . H2031 H 0.4818 0.3071 0.2284 0.0441 1.0000 Uiso R . . . . . . H2032 H 0.3579 0.3864 0.2163 0.0441 1.0000 Uiso R . . . . . . H2033 H 0.3588 0.2866 0.2033 0.0441 1.0000 Uiso R . . . . . . H1141 H -0.1446 0.3582 0.2238 0.0396 1.0000 Uiso R . . . . . . H1041 H 0.0192 0.4992 0.2267 0.0402 1.0000 Uiso R . . . . . . H941 H 0.2535 0.5165 0.2572 0.0398 1.0000 Uiso R . . . . . . H841 H 0.3283 0.3925 0.2847 0.0396 1.0000 Uiso R . . . . . . H541 H 0.3679 0.2269 0.3126 0.0387 1.0000 Uiso R . . . . . . H441 H 0.3300 0.0820 0.3286 0.0391 1.0000 Uiso R . . . . . . H341 H 0.1016 -0.0148 0.3124 0.0397 1.0000 Uiso R . . . . . . H241 H -0.0962 0.0373 0.2794 0.0393 1.0000 Uiso R . . . . . . H1541 H -0.3537 0.1110 0.1842 0.0407 1.0000 Uiso R . . . . . . H1641 H -0.6179 0.0725 0.2083 0.0406 1.0000 Uiso R . . . . . . H1741 H -0.6369 0.0985 0.2523 0.0404 1.0000 Uiso R . . . . . . H1841 H -0.3876 0.1601 0.2741 0.0404 1.0000 Uiso R . . . . . . H2041 H 0.0124 0.2648 0.1441 0.0479 1.0000 Uiso R . . . . . . H2042 H 0.1250 0.2905 0.1698 0.0479 1.0000 Uiso R . . . . . . H2043 H 0.1364 0.1892 0.1580 0.0479 1.0000 Uiso R . . . . . . H251 H 0.1049 0.2734 0.4698 0.0354 1.0000 Uiso R . . . . . . H351 H -0.0474 0.4119 0.4750 0.0363 1.0000 Uiso R . . . . . . H451 H -0.2782 0.4268 0.5054 0.0371 1.0000 Uiso R . . . . . . H551 H -0.3664 0.3039 0.5312 0.0368 1.0000 Uiso R . . . . . . H851 H -0.3957 0.1350 0.5560 0.0356 1.0000 Uiso R . . . . . . H951 H -0.3578 -0.0040 0.5735 0.0355 1.0000 Uiso R . . . . . . H1051 H -0.1197 -0.1025 0.5574 0.0355 1.0000 Uiso R . . . . . . H1151 H 0.0731 -0.0496 0.5245 0.0351 1.0000 Uiso R . . . . . . H1551 H 0.3369 0.0477 0.4273 0.0353 1.0000 Uiso R . . . . . . H1651 H 0.5932 -0.0020 0.4519 0.0357 1.0000 Uiso R . . . . . . H1751 H 0.5932 0.0029 0.4958 0.0357 1.0000 Uiso R . . . . . . H1851 H 0.3355 0.0593 0.5174 0.0356 1.0000 Uiso R . . . . . . H2051 H -0.0166 0.2220 0.3911 0.0410 1.0000 Uiso R . . . . . . H2052 H -0.1462 0.2316 0.4160 0.0410 1.0000 Uiso R . . . . . . H2053 H -0.1425 0.1380 0.3998 0.0410 1.0000 Uiso R . . . . . . H261 H 0.6191 0.0872 0.6391 0.0389 1.0000 Uiso R . . . . . . H361 H 0.4594 -0.0512 0.6394 0.0403 1.0000 Uiso R . . . . . . H461 H 0.2270 -0.0782 0.6102 0.0395 1.0000 Uiso R . . . . . . H561 H 0.1426 0.0304 0.5802 0.0395 1.0000 Uiso R . . . . . . H861 H 0.1143 0.2042 0.5491 0.0388 1.0000 Uiso R . . . . . . H961 H 0.1397 0.3507 0.5331 0.0392 1.0000 Uiso R . . . . . . H1061 H 0.3646 0.4462 0.5513 0.0393 1.0000 Uiso R . . . . . . H1161 H 0.5626 0.3992 0.5836 0.0387 1.0000 Uiso R . . . . . . H1561 H 0.8324 0.3692 0.6709 0.0382 1.0000 Uiso R . . . . . . H1661 H 1.1012 0.3845 0.6460 0.0375 1.0000 Uiso R . . . . . . H1761 H 1.1157 0.3206 0.6049 0.0379 1.0000 Uiso R . . . . . . H1861 H 0.8759 0.2469 0.5868 0.0377 1.0000 Uiso R . . . . . . H2061 H 0.4121 0.3114 0.7180 0.0445 1.0000 Uiso R . . . . . . H2062 H 0.3250 0.2406 0.6977 0.0445 1.0000 Uiso R . . . . . . H2063 H 0.2933 0.3482 0.6940 0.0445 1.0000 Uiso R . . . . . . H271 H -0.1132 0.0372 0.7766 0.0385 1.0000 Uiso R . . . . . . H371 H 0.0941 0.0080 0.8100 0.0393 1.0000 Uiso R . . . . . . H471 H 0.3151 0.1137 0.8208 0.0395 1.0000 Uiso R . . . . . . H571 H 0.3396 0.2505 0.7988 0.0390 1.0000 Uiso R . . . . . . H871 H 0.2763 0.4062 0.7651 0.0394 1.0000 Uiso R . . . . . . H971 H 0.1744 0.5073 0.7352 0.0396 1.0000 Uiso R . . . . . . H1071 H -0.0719 0.4708 0.7073 0.0403 1.0000 Uiso R . . . . . . H1171 H -0.2178 0.3255 0.7105 0.0399 1.0000 Uiso R . . . . . . H1571 H -0.4011 0.0491 0.6828 0.0387 1.0000 Uiso R . . . . . . H1671 H -0.6573 0.0377 0.7068 0.0380 1.0000 Uiso R . . . . . . H1771 H -0.6762 0.0851 0.7486 0.0372 1.0000 Uiso R . . . . . . H1871 H -0.4254 0.1596 0.7673 0.0370 1.0000 Uiso R . . . . . . H2071 H 0.0233 0.1007 0.6357 0.0458 1.0000 Uiso R . . . . . . H2072 H 0.1497 0.0728 0.6598 0.0458 1.0000 Uiso R . . . . . . H2073 H 0.0995 0.1780 0.6549 0.0458 1.0000 Uiso R . . . . . . H281 H 0.3891 0.4283 0.8323 0.0385 1.0000 Uiso R . . . . . . H381 H 0.6027 0.4571 0.7999 0.0400 1.0000 Uiso R . . . . . . H481 H 0.8214 0.3485 0.7893 0.0404 1.0000 Uiso R . . . . . . H581 H 0.8437 0.2124 0.8123 0.0394 1.0000 Uiso R . . . . . . H881 H 0.7924 0.0624 0.8490 0.0393 1.0000 Uiso R . . . . . . H981 H 0.6737 -0.0332 0.8824 0.0394 1.0000 Uiso R . . . . . . H1081 H 0.4289 0.0120 0.9063 0.0399 1.0000 Uiso R . . . . . . H1181 H 0.2841 0.1484 0.8985 0.0390 1.0000 Uiso R . . . . . . H1581 H 0.1287 0.4472 0.9224 0.0402 1.0000 Uiso R . . . . . . H1681 H -0.1541 0.4553 0.9004 0.0400 1.0000 Uiso R . . . . . . H1781 H -0.1825 0.3722 0.8604 0.0397 1.0000 Uiso R . . . . . . H1881 H 0.0577 0.2861 0.8443 0.0390 1.0000 Uiso R . . . . . . H2081 H 0.5397 0.4060 0.9693 0.0463 1.0000 Uiso R . . . . . . H2082 H 0.6230 0.3247 0.9521 0.0463 1.0000 Uiso R . . . . . . H2083 H 0.6606 0.4291 0.9442 0.0463 1.0000 Uiso R . . . . . . _refine_ls_extinction_method None #_oxford_refine_ls_scale 1.219(6) #loop_ # _oxford_twin_element_scale_factors # 0.814(5) # 0.186(5) 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 N11 . C121 . 1.475(11) yes N11 . C11 . 1.403(11) yes N11 . C131 . 1.370(12) yes O11 . C191 . 1.154(12) yes O21 . C191 . 1.350(13) yes O21 . C201 . 1.465(13) yes C121 . C111 . 1.279(12) yes C121 . C71 . 1.399(11) yes C111 . C101 . 1.305(12) yes C111 . H1111 . 0.950 no C101 . C91 . 1.363(13) yes C101 . H1011 . 0.950 no C91 . C81 . 1.328(13) yes C91 . H911 . 0.950 no C81 . C71 . 1.452(12) yes C81 . H811 . 0.950 no C71 . C61 . 1.477(11) yes C61 . C51 . 1.338(12) yes C61 . C11 . 1.443(11) yes C51 . C41 . 1.362(13) yes C51 . H511 . 0.950 no C41 . C31 . 1.379(13) yes C41 . H411 . 0.950 no C31 . C21 . 1.367(13) yes C31 . H311 . 0.950 no C21 . C11 . 1.380(12) yes C21 . H211 . 0.950 no C131 . C141 . 1.402(12) yes C131 . C181 . 1.461(12) yes C141 . C151 . 1.369(12) yes C141 . C191 . 1.463(12) yes C151 . C161 . 1.333(13) yes C151 . H1511 . 0.950 no C161 . C171 . 1.389(13) yes C161 . H1611 . 0.950 no C171 . C181 . 1.379(13) yes C171 . H1711 . 0.950 no C181 . H1811 . 0.950 no C201 . H2011 . 0.980 no C201 . H2012 . 0.980 no C201 . H2013 . 0.980 no N12 . C12 . 1.376(11) yes N12 . C122 . 1.437(11) yes N12 . C132 . 1.374(11) yes O12 . C192 . 1.249(12) yes O22 . C192 . 1.255(12) yes O22 . C202 . 1.466(13) yes C12 . C22 . 1.377(12) yes C12 . C62 . 1.422(11) yes C22 . C32 . 1.371(12) yes C22 . H221 . 0.950 no C32 . C42 . 1.383(12) yes C32 . H321 . 0.950 no C42 . C52 . 1.374(13) yes C42 . H421 . 0.950 no C52 . C62 . 1.370(12) yes C52 . H521 . 0.950 no C62 . C72 . 1.346(11) yes C72 . C82 . 1.456(12) yes C72 . C122 . 1.414(11) yes C82 . C92 . 1.389(13) yes C82 . H821 . 0.950 no C92 . C102 . 1.330(13) yes C92 . H921 . 0.950 no C102 . C112 . 1.399(12) yes C102 . H1021 . 0.950 no C112 . C122 . 1.347(12) yes C112 . H1121 . 0.950 no C132 . C142 . 1.348(12) yes C132 . C182 . 1.416(12) yes C142 . C152 . 1.366(12) yes C142 . C192 . 1.538(12) yes C152 . C162 . 1.320(12) yes C152 . H1521 . 0.950 no C162 . C172 . 1.384(13) yes C162 . H1621 . 0.950 no C172 . C182 . 1.406(12) yes C172 . H1721 . 0.950 no C182 . H1821 . 0.950 no C202 . H2021 . 0.980 no C202 . H2022 . 0.980 no C202 . H2023 . 0.980 no N13 . C13 . 1.395(11) yes N13 . C123 . 1.358(11) yes N13 . C133 . 1.419(11) yes O13 . C193 . 1.229(12) yes O23 . C193 . 1.356(12) yes O23 . C203 . 1.437(13) yes C13 . C23 . 1.371(12) yes C13 . C63 . 1.438(11) yes C23 . C33 . 1.370(12) yes C23 . H231 . 0.950 no C33 . C43 . 1.383(13) yes C33 . H331 . 0.950 no C43 . C53 . 1.358(13) yes C43 . H431 . 0.950 no C53 . C63 . 1.353(12) yes C53 . H531 . 0.950 no C63 . C73 . 1.410(11) yes C73 . C83 . 1.384(12) yes C73 . C123 . 1.456(11) yes C83 . C93 . 1.408(13) yes C83 . H831 . 0.950 no C93 . C103 . 1.348(12) yes C93 . H931 . 0.950 no C103 . C113 . 1.398(13) yes C103 . H1031 . 0.950 no C113 . C123 . 1.385(12) yes C113 . H1131 . 0.950 no C133 . C143 . 1.367(12) yes C133 . C183 . 1.449(12) yes C143 . C153 . 1.429(12) yes C143 . C193 . 1.423(12) yes C153 . C163 . 1.304(13) yes C153 . H1531 . 0.950 no C163 . C173 . 1.454(13) yes C163 . H1631 . 0.950 no C173 . C183 . 1.352(12) yes C173 . H1731 . 0.950 no C183 . H1831 . 0.950 no C203 . H2031 . 0.980 no C203 . H2032 . 0.980 no C203 . H2033 . 0.980 no N14 . C124 . 1.346(11) yes N14 . C14 . 1.380(11) yes N14 . C134 . 1.489(11) yes O14 . C194 . 1.229(12) yes O24 . C194 . 1.325(12) yes O24 . C204 . 1.409(13) yes C124 . C114 . 1.473(12) yes C124 . C74 . 1.418(11) yes C114 . C104 . 1.431(12) yes C114 . H1141 . 0.950 no C104 . C94 . 1.408(13) yes C104 . H1041 . 0.950 no C94 . C84 . 1.404(13) yes C94 . H941 . 0.950 no C84 . C74 . 1.321(12) yes C84 . H841 . 0.950 no C74 . C64 . 1.408(11) yes C64 . C54 . 1.453(12) yes C64 . C14 . 1.354(11) yes C54 . C44 . 1.363(12) yes C54 . H541 . 0.950 no C44 . C34 . 1.388(13) yes C44 . H441 . 0.950 no C34 . C24 . 1.384(12) yes C34 . H341 . 0.950 no C24 . C14 . 1.380(12) yes C24 . H241 . 0.950 no C134 . C144 . 1.361(12) yes C134 . C184 . 1.344(12) yes C144 . C154 . 1.409(12) yes C144 . C194 . 1.516(12) yes C154 . C164 . 1.415(13) yes C154 . H1541 . 0.950 no C164 . C174 . 1.348(13) yes C164 . H1641 . 0.950 no C174 . C184 . 1.373(12) yes C174 . H1741 . 0.950 no C184 . H1841 . 0.950 no C204 . H2041 . 0.980 no C204 . H2042 . 0.980 no C204 . H2043 . 0.980 no N15 . C15 . 1.392(11) yes N15 . C125 . 1.424(11) yes N15 . C135 . 1.429(12) yes O15 . C195 . 1.183(12) yes O25 . C195 . 1.287(12) yes O25 . C205 . 1.451(13) yes C15 . C25 . 1.382(12) yes C15 . C65 . 1.357(11) yes C25 . C35 . 1.370(12) yes C25 . H251 . 0.950 no C35 . C45 . 1.383(13) yes C35 . H351 . 0.950 no C45 . C55 . 1.364(13) yes C45 . H451 . 0.950 no C55 . C65 . 1.433(12) yes C55 . H551 . 0.950 no C65 . C75 . 1.463(11) yes C75 . C85 . 1.395(12) yes C75 . C125 . 1.344(11) yes C85 . C95 . 1.283(12) yes C85 . H851 . 0.950 no C95 . C105 . 1.457(12) yes C95 . H951 . 0.950 no C105 . C115 . 1.370(12) yes C105 . H1051 . 0.950 no C115 . C125 . 1.350(12) yes C115 . H1151 . 0.950 no C135 . C145 . 1.412(12) yes C135 . C185 . 1.305(12) yes C145 . C155 . 1.337(12) yes C145 . C195 . 1.564(12) yes C155 . C165 . 1.430(12) yes C155 . H1551 . 0.950 no C165 . C175 . 1.298(13) yes C165 . H1651 . 0.950 no C175 . C185 . 1.402(12) yes C175 . H1751 . 0.950 no C185 . H1851 . 0.950 no C205 . H2051 . 0.980 no C205 . H2052 . 0.980 no C205 . H2053 . 0.980 no N16 . C16 . 1.399(11) yes N16 . C126 . 1.327(11) yes N16 . C136 . 1.477(11) yes O16 . C196 . 1.130(12) yes O26 . C196 . 1.401(12) yes O26 . C206 . 1.443(13) yes C16 . C26 . 1.375(12) yes C16 . C66 . 1.396(11) yes C26 . C36 . 1.380(12) yes C26 . H261 . 0.950 no C36 . C46 . 1.377(13) yes C36 . H361 . 0.950 no C46 . C56 . 1.348(13) yes C46 . H461 . 0.950 no C56 . C66 . 1.406(12) yes C56 . H561 . 0.950 no C66 . C76 . 1.525(11) yes C76 . C86 . 1.362(12) yes C76 . C126 . 1.402(11) yes C86 . C96 . 1.333(12) yes C86 . H861 . 0.950 no C96 . C106 . 1.420(13) yes C96 . H961 . 0.950 no C106 . C116 . 1.369(12) yes C106 . H1061 . 0.950 no C116 . C126 . 1.385(12) yes C116 . H1161 . 0.950 no C136 . C146 . 1.467(12) yes C136 . C186 . 1.335(12) yes C146 . C156 . 1.406(12) yes C146 . C196 . 1.423(12) yes C156 . C166 . 1.420(12) yes C156 . H1561 . 0.950 no C166 . C176 . 1.364(13) yes C166 . H1661 . 0.950 no C176 . C186 . 1.330(12) yes C176 . H1761 . 0.950 no C186 . H1861 . 0.950 no C206 . H2061 . 0.980 no C206 . H2062 . 0.980 no C206 . H2063 . 0.980 no N17 . C17 . 1.393(11) yes N17 . C127 . 1.402(11) yes N17 . C137 . 1.450(11) yes O17 . C197 . 1.120(12) yes O27 . C197 . 1.353(13) yes O27 . C207 . 1.479(13) yes C17 . C27 . 1.373(12) yes C17 . C67 . 1.448(11) yes C27 . C37 . 1.372(12) yes C27 . H271 . 0.950 no C37 . C47 . 1.379(12) yes C37 . H371 . 0.950 no C47 . C57 . 1.360(13) yes C47 . H471 . 0.950 no C57 . C67 . 1.342(12) yes C57 . H571 . 0.950 no C67 . C77 . 1.443(11) yes C77 . C87 . 1.359(12) yes C77 . C127 . 1.406(11) yes C87 . C97 . 1.331(13) yes C87 . H871 . 0.950 no C97 . C107 . 1.433(13) yes C97 . H971 . 0.950 no C107 . C117 . 1.396(12) yes C107 . H1071 . 0.950 no C117 . C127 . 1.432(12) yes C117 . H1171 . 0.950 no C137 . C147 . 1.359(12) yes C137 . C187 . 1.410(12) yes C147 . C157 . 1.390(12) yes C147 . C197 . 1.498(12) yes C157 . C167 . 1.341(13) yes C157 . H1571 . 0.950 no C167 . C177 . 1.319(13) yes C167 . H1671 . 0.950 no C177 . C187 . 1.375(12) yes C177 . H1771 . 0.950 no C187 . H1871 . 0.950 no C207 . H2071 . 0.980 no C207 . H2072 . 0.980 no C207 . H2073 . 0.980 no N18 . C18 . 1.374(11) yes N18 . C128 . 1.368(11) yes N18 . C138 . 1.439(11) yes O18 . C198 . 1.235(12) yes O28 . C198 . 1.312(12) yes O28 . C208 . 1.398(13) yes C18 . C28 . 1.373(12) yes C18 . C68 . 1.359(11) yes C28 . C38 . 1.364(12) yes C28 . H281 . 0.950 no C38 . C48 . 1.393(13) yes C38 . H381 . 0.950 no C48 . C58 . 1.361(13) yes C48 . H481 . 0.950 no C58 . C68 . 1.436(12) yes C58 . H581 . 0.950 no C68 . C78 . 1.438(11) yes C78 . C88 . 1.427(12) yes C78 . C128 . 1.378(11) yes C88 . C98 . 1.401(13) yes C88 . H881 . 0.950 no C98 . C108 . 1.349(13) yes C98 . H981 . 0.950 no C108 . C118 . 1.357(12) yes C108 . H1081 . 0.950 no C118 . C128 . 1.333(12) yes C118 . H1181 . 0.950 no C138 . C148 . 1.393(12) yes C138 . C188 . 1.327(12) yes C148 . C158 . 1.408(12) yes C148 . C198 . 1.476(12) yes C158 . C168 . 1.401(12) yes C158 . H1581 . 0.950 no C168 . C178 . 1.422(13) yes C168 . H1681 . 0.950 no C178 . C188 . 1.387(12) yes C178 . H1781 . 0.950 no C188 . H1881 . 0.950 no C208 . H2081 . 0.980 no C208 . H2082 . 0.980 no C208 . H2083 . 0.980 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 C121 . N11 . C11 . 109.3(4) yes C121 . N11 . C131 . 124.0(5) yes C11 . N11 . C131 . 126.7(5) yes C191 . O21 . C201 . 118.5(7) yes N11 . C121 . C111 . 130.9(5) yes N11 . C121 . C71 . 105.2(4) yes C111 . C121 . C71 . 123.6(5) yes C121 . C111 . C101 . 117.2(6) yes C121 . C111 . H1111 . 121.3 no C101 . C111 . H1111 . 121.6 no C111 . C101 . C91 . 124.5(6) yes C111 . C101 . H1011 . 119.0 no C91 . C101 . H1011 . 116.6 no C101 . C91 . C81 . 122.2(6) yes C101 . C91 . H911 . 122.1 no C81 . C91 . H911 . 115.7 no C91 . C81 . C71 . 114.0(5) yes C91 . C81 . H811 . 123.6 no C71 . C81 . H811 . 122.4 no C81 . C71 . C121 . 118.6(5) yes C81 . C71 . C61 . 129.7(5) yes C121 . C71 . C61 . 111.5(5) yes C71 . C61 . C51 . 136.8(5) yes C71 . C61 . C11 . 104.2(4) yes C51 . C61 . C11 . 118.9(5) yes C61 . C51 . C41 . 120.3(6) yes C61 . C51 . H511 . 120.3 no C41 . C51 . H511 . 119.4 no C51 . C41 . C31 . 121.1(6) yes C51 . C41 . H411 . 122.5 no C31 . C41 . H411 . 116.3 no C41 . C31 . C21 . 121.3(6) yes C41 . C31 . H311 . 120.4 no C21 . C31 . H311 . 118.2 no C31 . C21 . C11 . 117.6(5) yes C31 . C21 . H211 . 120.9 no C11 . C21 . H211 . 121.4 no C61 . C11 . N11 . 109.8(4) yes C61 . C11 . C21 . 120.7(4) yes N11 . C11 . C21 . 129.6(5) yes N11 . C131 . C141 . 127.1(5) yes N11 . C131 . C181 . 116.3(5) yes C141 . C131 . C181 . 116.7(5) yes C131 . C141 . C151 . 119.8(5) yes C131 . C141 . C191 . 115.4(5) yes C151 . C141 . C191 . 124.5(6) yes C141 . C151 . C161 . 124.6(6) yes C141 . C151 . H1511 . 117.9 no C161 . C151 . H1511 . 117.5 no C151 . C161 . C171 . 118.0(6) yes C151 . C161 . H1611 . 121.2 no C171 . C161 . H1611 . 120.8 no C161 . C171 . C181 . 121.7(6) yes C161 . C171 . H1711 . 119.4 no C181 . C171 . H1711 . 119.0 no C131 . C181 . C171 . 119.3(5) yes C131 . C181 . H1811 . 120.1 no C171 . C181 . H1811 . 120.6 no C141 . C191 . O21 . 107.8(5) yes C141 . C191 . O11 . 134.4(6) yes O21 . C191 . O11 . 117.5(6) yes O21 . C201 . H2011 . 109.4 no O21 . C201 . H2012 . 109.3 no H2011 . C201 . H2012 . 109.5 no O21 . C201 . H2013 . 109.7 no H2011 . C201 . H2013 . 109.5 no H2012 . C201 . H2013 . 109.5 no C12 . N12 . C122 . 106.8(4) yes C12 . N12 . C132 . 129.0(5) yes C122 . N12 . C132 . 122.9(5) yes C192 . O22 . C202 . 117.2(7) yes N12 . C12 . C22 . 129.0(5) yes N12 . C12 . C62 . 109.5(4) yes C22 . C12 . C62 . 121.6(5) yes C12 . C22 . C32 . 117.8(5) yes C12 . C22 . H221 . 121.1 no C32 . C22 . H221 . 121.1 no C22 . C32 . C42 . 121.1(6) yes C22 . C32 . H321 . 119.4 no C42 . C32 . H321 . 119.4 no C32 . C42 . C52 . 121.3(6) yes C32 . C42 . H421 . 119.3 no C52 . C42 . H421 . 119.3 no C42 . C52 . C62 . 119.1(5) yes C42 . C52 . H521 . 120.4 no C62 . C52 . H521 . 120.4 no C12 . C62 . C52 . 119.0(5) yes C12 . C62 . C72 . 107.1(4) yes C52 . C62 . C72 . 133.9(5) yes C62 . C72 . C82 . 136.4(5) yes C62 . C72 . C122 . 110.4(4) yes C82 . C72 . C122 . 113.2(5) yes C72 . C82 . C92 . 118.4(5) yes C72 . C82 . H821 . 120.8 no C92 . C82 . H821 . 120.8 no C82 . C92 . C102 . 125.9(6) yes C82 . C92 . H921 . 117.0 no C102 . C92 . H921 . 117.1 no C92 . C102 . C112 . 117.0(6) yes C92 . C102 . H1021 . 121.5 no C112 . C102 . H1021 . 121.5 no C102 . C112 . C122 . 119.9(5) yes C102 . C112 . H1121 . 120.0 no C122 . C112 . H1121 . 120.1 no N12 . C122 . C72 . 106.0(4) yes N12 . C122 . C112 . 128.4(5) yes C72 . C122 . C112 . 125.5(5) yes N12 . C132 . C142 . 128.1(5) yes N12 . C132 . C182 . 116.5(5) yes C142 . C132 . C182 . 115.2(5) yes C132 . C142 . C152 . 122.6(5) yes C132 . C142 . C192 . 118.5(5) yes C152 . C142 . C192 . 118.8(5) yes C142 . C152 . C162 . 122.3(6) yes C142 . C152 . H1521 . 118.8 no C162 . C152 . H1521 . 118.9 no C152 . C162 . C172 . 120.3(6) yes C152 . C162 . H1621 . 119.8 no C172 . C162 . H1621 . 119.9 no C162 . C172 . C182 . 116.9(6) yes C162 . C172 . H1721 . 121.5 no C182 . C172 . H1721 . 121.6 no C132 . C182 . C172 . 122.6(6) yes C132 . C182 . H1821 . 118.7 no C172 . C182 . H1821 . 118.7 no C142 . C192 . O22 . 114.1(5) yes C142 . C192 . O12 . 122.1(5) yes O22 . C192 . O12 . 123.8(6) yes O22 . C202 . H2021 . 109.5 no O22 . C202 . H2022 . 109.6 no H2021 . C202 . H2022 . 109.5 no O22 . C202 . H2023 . 109.3 no H2021 . C202 . H2023 . 109.5 no H2022 . C202 . H2023 . 109.5 no C13 . N13 . C123 . 108.1(4) yes C13 . N13 . C133 . 124.1(5) yes C123 . N13 . C133 . 127.7(5) yes C193 . O23 . C203 . 118.6(7) yes N13 . C13 . C23 . 129.7(5) yes N13 . C13 . C63 . 109.3(4) yes C23 . C13 . C63 . 120.9(5) yes C13 . C23 . C33 . 117.7(5) yes C13 . C23 . H231 . 121.1 no C33 . C23 . H231 . 121.2 no C23 . C33 . C43 . 121.3(6) yes C23 . C33 . H331 . 119.3 no C43 . C33 . H331 . 119.4 no C33 . C43 . C53 . 121.4(6) yes C33 . C43 . H431 . 119.3 no C53 . C43 . H431 . 119.3 no C43 . C53 . C63 . 119.6(5) yes C43 . C53 . H531 . 120.2 no C63 . C53 . H531 . 120.2 no C13 . C63 . C53 . 119.1(5) yes C13 . C63 . C73 . 106.5(4) yes C53 . C63 . C73 . 134.3(5) yes C63 . C73 . C83 . 136.4(5) yes C63 . C73 . C123 . 106.3(4) yes C83 . C73 . C123 . 117.0(5) yes C73 . C83 . C93 . 119.5(5) yes C73 . C83 . H831 . 120.2 no C93 . C83 . H831 . 120.3 no C83 . C93 . C103 . 122.0(6) yes C83 . C93 . H931 . 118.9 no C103 . C93 . H931 . 119.0 no C93 . C103 . C113 . 122.0(6) yes C93 . C103 . H1031 . 118.9 no C113 . C103 . H1031 . 119.1 no C103 . C113 . C123 . 116.8(5) yes C103 . C113 . H1131 . 121.5 no C123 . C113 . H1131 . 121.7 no C73 . C123 . C113 . 122.8(5) yes C73 . C123 . N13 . 109.6(4) yes C113 . C123 . N13 . 127.7(5) yes N13 . C133 . C143 . 119.8(5) yes N13 . C133 . C183 . 118.6(5) yes C143 . C133 . C183 . 121.6(5) yes C133 . C143 . C153 . 116.6(5) yes C133 . C143 . C193 . 123.1(5) yes C153 . C143 . C193 . 120.3(5) yes C143 . C153 . C163 . 125.0(6) yes C143 . C153 . H1531 . 117.5 no C163 . C153 . H1531 . 117.5 no C153 . C163 . C173 . 117.3(6) yes C153 . C163 . H1631 . 121.4 no C173 . C163 . H1631 . 121.4 no C163 . C173 . C183 . 121.9(6) yes C163 . C173 . H1731 . 119.1 no C183 . C173 . H1731 . 119.0 no C133 . C183 . C173 . 117.6(5) yes C133 . C183 . H1831 . 121.1 no C173 . C183 . H1831 . 121.2 no C143 . C193 . O23 . 114.2(5) yes C143 . C193 . O13 . 128.4(6) yes O23 . C193 . O13 . 117.2(6) yes O23 . C203 . H2031 . 109.5 no O23 . C203 . H2032 . 109.9 no H2031 . C203 . H2032 . 109.5 no O23 . C203 . H2033 . 109.0 no H2031 . C203 . H2033 . 109.5 no H2032 . C203 . H2033 . 109.5 no C124 . N14 . C14 . 108.2(4) yes C124 . N14 . C134 . 126.0(5) yes C14 . N14 . C134 . 125.7(5) yes C194 . O24 . C204 . 114.9(7) yes N14 . C124 . C114 . 128.5(5) yes N14 . C124 . C74 . 110.6(4) yes C114 . C124 . C74 . 120.9(4) yes C124 . C114 . C104 . 116.7(5) yes C124 . C114 . H1141 . 122.0 no C104 . C114 . H1141 . 121.4 no C114 . C104 . C94 . 120.5(5) yes C114 . C104 . H1041 . 119.4 no C94 . C104 . H1041 . 120.2 no C104 . C94 . C84 . 118.3(5) yes C104 . C94 . H941 . 118.4 no C84 . C94 . H941 . 123.2 no C94 . C84 . C74 . 125.5(6) yes C94 . C84 . H841 . 117.1 no C74 . C84 . H841 . 117.4 no C124 . C74 . C84 . 118.2(5) yes C124 . C74 . C64 . 102.7(4) yes C84 . C74 . C64 . 139.1(5) yes C74 . C64 . C54 . 130.5(5) yes C74 . C64 . C14 . 111.0(5) yes C54 . C64 . C14 . 118.6(4) yes C64 . C54 . C44 . 117.9(5) yes C64 . C54 . H541 . 120.4 no C44 . C54 . H541 . 121.7 no C54 . C44 . C34 . 121.5(6) yes C54 . C44 . H441 . 116.5 no C34 . C44 . H441 . 122.0 no C44 . C34 . C24 . 121.0(6) yes C44 . C34 . H341 . 118.7 no C24 . C34 . H341 . 120.2 no C34 . C24 . C14 . 117.5(6) yes C34 . C24 . H241 . 121.2 no C14 . C24 . H241 . 121.2 no C24 . C14 . N14 . 129.0(5) yes C24 . C14 . C64 . 123.5(5) yes N14 . C14 . C64 . 107.5(4) yes N14 . C134 . C144 . 117.5(5) yes N14 . C134 . C184 . 119.7(5) yes C144 . C134 . C184 . 122.6(5) yes C134 . C144 . C154 . 118.6(5) yes C134 . C144 . C194 . 126.5(5) yes C154 . C144 . C194 . 114.7(5) yes C144 . C154 . C164 . 117.0(5) yes C144 . C154 . H1541 . 121.5 no C164 . C154 . H1541 . 121.5 no C154 . C164 . C174 . 122.4(6) yes C154 . C164 . H1641 . 118.8 no C174 . C164 . H1641 . 118.7 no C164 . C174 . C184 . 118.5(6) yes C164 . C174 . H1741 . 120.7 no C184 . C174 . H1741 . 120.8 no C174 . C184 . C134 . 120.8(6) yes C174 . C184 . H1841 . 119.6 no C134 . C184 . H1841 . 119.6 no C144 . C194 . O24 . 113.8(5) yes C144 . C194 . O14 . 119.8(6) yes O24 . C194 . O14 . 126.5(6) yes O24 . C204 . H2041 . 109.3 no O24 . C204 . H2042 . 109.6 no H2041 . C204 . H2042 . 109.5 no O24 . C204 . H2043 . 109.5 no H2041 . C204 . H2043 . 109.5 no H2042 . C204 . H2043 . 109.5 no C15 . N15 . C125 . 108.9(4) yes C15 . N15 . C135 . 128.0(5) yes C125 . N15 . C135 . 123.0(5) yes C195 . O25 . C205 . 114.4(7) yes N15 . C15 . C25 . 129.3(5) yes N15 . C15 . C65 . 107.5(4) yes C25 . C15 . C65 . 122.9(5) yes C15 . C25 . C35 . 117.7(5) yes C15 . C25 . H251 . 121.2 no C35 . C25 . H251 . 121.1 no C25 . C35 . C45 . 121.2(6) yes C25 . C35 . H351 . 119.4 no C45 . C35 . H351 . 119.4 no C35 . C45 . C55 . 121.4(6) yes C35 . C45 . H451 . 119.2 no C55 . C45 . H451 . 119.4 no C45 . C55 . C65 . 117.9(5) yes C45 . C55 . H551 . 121.0 no C65 . C55 . H551 . 121.0 no C55 . C65 . C15 . 118.9(5) yes C55 . C65 . C75 . 132.2(5) yes C15 . C65 . C75 . 108.4(4) yes C65 . C75 . C85 . 131.3(5) yes C65 . C75 . C125 . 107.3(4) yes C85 . C75 . C125 . 121.4(5) yes C75 . C85 . C95 . 119.9(5) yes C75 . C85 . H851 . 120.1 no C95 . C85 . H851 . 120.0 no C85 . C95 . C105 . 119.6(6) yes C85 . C95 . H951 . 120.2 no C105 . C95 . H951 . 120.2 no C95 . C105 . C115 . 119.5(6) yes C95 . C105 . H1051 . 120.2 no C115 . C105 . H1051 . 120.2 no C105 . C115 . C125 . 118.6(5) yes C105 . C115 . H1151 . 120.8 no C125 . C115 . H1151 . 120.7 no N15 . C125 . C115 . 131.2(5) yes N15 . C125 . C75 . 107.8(4) yes C115 . C125 . C75 . 121.0(5) yes N15 . C135 . C145 . 122.3(5) yes N15 . C135 . C185 . 119.3(5) yes C145 . C135 . C185 . 118.3(5) yes C135 . C145 . C155 . 120.8(5) yes C135 . C145 . C195 . 120.8(5) yes C155 . C145 . C195 . 118.4(5) yes C145 . C155 . C165 . 117.7(5) yes C145 . C155 . H1551 . 121.2 no C165 . C155 . H1551 . 121.1 no C155 . C165 . C175 . 122.2(6) yes C155 . C165 . H1651 . 119.0 no C175 . C165 . H1651 . 118.9 no C165 . C175 . C185 . 117.9(6) yes C165 . C175 . H1751 . 121.1 no C185 . C175 . H1751 . 121.0 no C175 . C185 . C135 . 123.2(6) yes C175 . C185 . H1851 . 118.4 no C135 . C185 . H1851 . 118.4 no C145 . C195 . O25 . 108.1(5) yes C145 . C195 . O15 . 120.4(5) yes O25 . C195 . O15 . 131.4(6) yes O25 . C205 . H2051 . 109.5 no O25 . C205 . H2052 . 109.6 no H2051 . C205 . H2052 . 109.5 no O25 . C205 . H2053 . 109.3 no H2051 . C205 . H2053 . 109.5 no H2052 . C205 . H2053 . 109.5 no C16 . N16 . C126 . 109.7(4) yes C16 . N16 . C136 . 123.7(5) yes C126 . N16 . C136 . 126.5(5) yes C196 . O26 . C206 . 114.6(7) yes N16 . C16 . C26 . 129.9(5) yes N16 . C16 . C66 . 108.6(4) yes C26 . C16 . C66 . 121.6(5) yes C16 . C26 . C36 . 117.5(5) yes C16 . C26 . H261 . 121.2 no C36 . C26 . H261 . 121.3 no C26 . C36 . C46 . 121.6(6) yes C26 . C36 . H361 . 119.2 no C46 . C36 . H361 . 119.2 no C36 . C46 . C56 . 121.3(6) yes C36 . C46 . H461 . 119.3 no C56 . C46 . H461 . 119.3 no C46 . C56 . C66 . 118.9(5) yes C46 . C56 . H561 . 120.5 no C66 . C56 . H561 . 120.6 no C56 . C66 . C16 . 119.1(5) yes C56 . C66 . C76 . 134.8(5) yes C16 . C66 . C76 . 106.0(4) yes C66 . C76 . C86 . 135.5(5) yes C66 . C76 . C126 . 103.1(4) yes C86 . C76 . C126 . 121.2(5) yes C76 . C86 . C96 . 121.5(5) yes C76 . C86 . H861 . 119.2 no C96 . C86 . H861 . 119.3 no C86 . C96 . C106 . 116.4(6) yes C86 . C96 . H961 . 121.9 no C106 . C96 . H961 . 121.7 no C96 . C106 . C116 . 125.2(6) yes C96 . C106 . H1061 . 117.4 no C116 . C106 . H1061 . 117.3 no C106 . C116 . C126 . 115.5(5) yes C106 . C116 . H1161 . 122.2 no C126 . C116 . H1161 . 122.3 no C76 . C126 . C116 . 120.1(5) yes C76 . C126 . N16 . 112.4(4) yes C116 . C126 . N16 . 127.6(5) yes N16 . C136 . C146 . 114.9(5) yes N16 . C136 . C186 . 119.7(5) yes C146 . C136 . C186 . 124.8(5) yes C136 . C146 . C156 . 112.4(5) yes C136 . C146 . C196 . 123.0(5) yes C156 . C146 . C196 . 124.6(5) yes C146 . C156 . C166 . 121.9(5) yes C146 . C156 . H1561 . 119.1 no C166 . C156 . H1561 . 119.0 no C156 . C166 . C176 . 118.8(6) yes C156 . C166 . H1661 . 120.6 no C176 . C166 . H1661 . 120.6 no C166 . C176 . C186 . 122.8(6) yes C166 . C176 . H1761 . 118.6 no C186 . C176 . H1761 . 118.6 no C136 . C186 . C176 . 119.2(6) yes C136 . C186 . H1861 . 120.4 no C176 . C186 . H1861 . 120.4 no C146 . C196 . O26 . 108.8(5) yes C146 . C196 . O16 . 130.5(6) yes O26 . C196 . O16 . 120.7(6) yes O26 . C206 . H2061 . 109.4 no O26 . C206 . H2062 . 109.5 no H2061 . C206 . H2062 . 109.5 no O26 . C206 . H2063 . 109.4 no H2061 . C206 . H2063 . 109.5 no H2062 . C206 . H2063 . 109.5 no C17 . N17 . C127 . 107.6(4) yes C17 . N17 . C137 . 122.9(5) yes C127 . N17 . C137 . 128.8(5) yes C197 . O27 . C207 . 112.0(7) yes N17 . C17 . C27 . 129.7(5) yes N17 . C17 . C67 . 109.5(4) yes C27 . C17 . C67 . 120.7(5) yes C17 . C27 . C37 . 117.6(5) yes C17 . C27 . H271 . 121.2 no C37 . C27 . H271 . 121.2 no C27 . C37 . C47 . 121.3(6) yes C27 . C37 . H371 . 119.3 no C47 . C37 . H371 . 119.3 no C37 . C47 . C57 . 121.3(6) yes C37 . C47 . H471 . 119.3 no C57 . C47 . H471 . 119.4 no C47 . C57 . C67 . 120.0(5) yes C47 . C57 . H571 . 120.0 no C67 . C57 . H571 . 120.0 no C17 . C67 . C57 . 119.0(5) yes C17 . C67 . C77 . 105.3(4) yes C57 . C67 . C77 . 135.7(5) yes C67 . C77 . C87 . 136.0(5) yes C67 . C77 . C127 . 107.8(4) yes C87 . C77 . C127 . 116.2(5) yes C77 . C87 . C97 . 123.0(5) yes C77 . C87 . H871 . 118.5 no C97 . C87 . H871 . 118.5 no C87 . C97 . C107 . 120.9(6) yes C87 . C97 . H971 . 119.5 no C107 . C97 . H971 . 119.6 no C97 . C107 . C117 . 121.0(6) yes C97 . C107 . H1071 . 119.5 no C117 . C107 . H1071 . 119.5 no C107 . C117 . C127 . 113.6(5) yes C107 . C117 . H1171 . 123.2 no C127 . C117 . H1171 . 123.2 no C117 . C127 . C77 . 125.4(5) yes C117 . C127 . N17 . 124.8(5) yes C77 . C127 . N17 . 109.7(4) yes N17 . C137 . C147 . 124.0(5) yes N17 . C137 . C187 . 114.5(5) yes C147 . C137 . C187 . 121.1(5) yes C137 . C147 . C157 . 117.0(5) yes C137 . C147 . C197 . 118.6(5) yes C157 . C147 . C197 . 124.3(5) yes C147 . C157 . C167 . 120.3(5) yes C147 . C157 . H1571 . 119.8 no C167 . C157 . H1571 . 119.9 no C157 . C167 . C177 . 124.3(6) yes C157 . C167 . H1671 . 117.8 no C177 . C167 . H1671 . 118.0 no C167 . C177 . C187 . 117.9(6) yes C167 . C177 . H1771 . 121.0 no C187 . C177 . H1771 . 121.2 no C137 . C187 . C177 . 119.4(6) yes C137 . C187 . H1871 . 120.4 no C177 . C187 . H1871 . 120.2 no C147 . C197 . O27 . 106.4(5) yes C147 . C197 . O17 . 126.9(6) yes O27 . C197 . O17 . 126.7(6) yes O27 . C207 . H2071 . 109.5 no O27 . C207 . H2072 . 109.3 no H2071 . C207 . H2072 . 109.5 no O27 . C207 . H2073 . 109.6 no H2071 . C207 . H2073 . 109.5 no H2072 . C207 . H2073 . 109.5 no C18 . N18 . C128 . 109.8(4) yes C18 . N18 . C138 . 126.2(5) yes C128 . N18 . C138 . 123.6(5) yes C198 . O28 . C208 . 119.9(7) yes N18 . C18 . C28 . 129.2(5) yes N18 . C18 . C68 . 107.4(4) yes C28 . C18 . C68 . 123.3(5) yes C18 . C28 . C38 . 117.7(5) yes C18 . C28 . H281 . 121.2 no C38 . C28 . H281 . 121.2 no C28 . C38 . C48 . 121.2(6) yes C28 . C38 . H381 . 119.4 no C48 . C38 . H381 . 119.4 no C38 . C48 . C58 . 121.4(6) yes C38 . C48 . H481 . 119.2 no C58 . C48 . H481 . 119.3 no C48 . C58 . C68 . 117.6(5) yes C48 . C58 . H581 . 121.2 no C68 . C58 . H581 . 121.2 no C58 . C68 . C18 . 118.9(5) yes C58 . C68 . C78 . 132.8(5) yes C18 . C68 . C78 . 108.3(4) yes C68 . C78 . C88 . 133.7(5) yes C68 . C78 . C128 . 105.9(4) yes C88 . C78 . C128 . 120.4(5) yes C78 . C88 . C98 . 115.7(5) yes C78 . C88 . H881 . 122.2 no C98 . C88 . H881 . 122.2 no C88 . C98 . C108 . 121.1(6) yes C88 . C98 . H981 . 119.4 no C108 . C98 . H981 . 119.5 no C98 . C108 . C118 . 122.0(6) yes C98 . C108 . H1081 . 119.0 no C118 . C108 . H1081 . 119.0 no C108 . C118 . C128 . 119.8(5) yes C108 . C118 . H1181 . 120.1 no C128 . C118 . H1181 . 120.1 no C78 . C128 . N18 . 108.3(4) yes C78 . C128 . C118 . 121.1(5) yes N18 . C128 . C118 . 130.5(5) yes N18 . C138 . C148 . 119.1(5) yes N18 . C138 . C188 . 119.4(5) yes C148 . C138 . C188 . 121.3(5) yes C138 . C148 . C158 . 119.1(5) yes C138 . C148 . C198 . 124.5(5) yes C158 . C148 . C198 . 116.3(5) yes C148 . C158 . C168 . 121.1(5) yes C148 . C158 . H1581 . 119.4 no C168 . C158 . H1581 . 119.5 no C158 . C168 . C178 . 116.3(6) yes C158 . C168 . H1681 . 121.8 no C178 . C168 . H1681 . 121.9 no C168 . C178 . C188 . 121.5(6) yes C168 . C178 . H1781 . 119.2 no C188 . C178 . H1781 . 119.3 no C178 . C188 . C138 . 120.7(5) yes C178 . C188 . H1881 . 119.6 no C138 . C188 . H1881 . 119.7 no C148 . C198 . O28 . 117.2(5) yes C148 . C198 . O18 . 124.7(5) yes O28 . C198 . O18 . 118.0(6) yes O28 . C208 . H2081 . 109.5 no O28 . C208 . H2082 . 109.4 no H2081 . C208 . H2082 . 109.5 no O28 . C208 . H2083 . 109.5 no H2081 . C208 . H2083 . 109.5 no H2082 . C208 . H2083 . 109.5 no _chemical_name_common 'Methyl 2-(9H-carbazol-9-yl)benzoate' _exptl_crystal_recrystallization_method ; A mixture of carbazole, methyl 2-iodobenzoate, copper powder, potassium carbonate and nitrobenzene were heated at 175 degrees C for 48 h. After cooling, the resultant mixture was a red solid. A mixture of water/chloroform (1:1) was added to the solid, and the two layers separated. The aqueous layer was then extracted twice with chloroform, and the organic layers were combined and dried over MgSO4. The solvent was removed under reduced pressure, and the residue oil was purified by flash dry chromatography on silica using hexane/ethyl acetate (85:15) as the eluant. This resulted in the formation of colourless crystals. (5.30 g, 88%) ; #edit data_2_2GPa_I.cif _database_code_depnum_ccdc_archive 'CCDC 752557' #_oxford_structure_analysis_title 'mben06 in Pn' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 7.2634(3) _cell_length_b 14.4120(11) _cell_length_c 50.836(4) _cell_angle_alpha 90 _cell_angle_beta 89.966(5) _cell_angle_gamma 90 _cell_volume 5321.6(7) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 n 1 ' _symmetry_space_group_name_Hall 'P -2yac' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y,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 0.0000 0.0010 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0010 0.0010 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0030 0.0030 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 16 # Given Formula = C15 H11.25 N0.75 O1.50 # Dc = 1.13 Fooo = 2528.00 Mu = 0.73 M = 1808.07 # Found Formula = C20 H15 N1 O2 # Dc = 1.50 FOOO = 2528.00 Mu = 0.97 M = 2410.76 _chemical_formula_sum 'C20 H15 N1 O2' _chemical_formula_moiety 'C20 H15 N1 O2' _chemical_compound_source ? _chemical_formula_weight 301.34 _cell_measurement_reflns_used 1076 _cell_measurement_theta_min 2 _cell_measurement_theta_max 12 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.504 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 2528 _exptl_absorpt_coefficient_mu 0.097 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.80 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device APEX-II _diffrn_measurement_device_type Area _diffrn_radiation_monochromator silicon _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.47620 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 293 _diffrn_ambient_pressure 2200000 _diffrn_reflns_number 18915 _reflns_number_total 4090 _diffrn_reflns_av_R_equivalents 0.1504 # Number of reflections with Friedels Law is 4090 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5403 _diffrn_reflns_reduction_process ; Merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 ; _diffrn_reflns_theta_min 0.984 _diffrn_reflns_theta_max 13.654 _diffrn_measured_fraction_theta_max 0.753 _diffrn_reflns_theta_full 10.240 _diffrn_measured_fraction_theta_full 0.800 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 43 _reflns_limit_h_min -7 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 43 #_oxford_diffrn_Wilson_B_factor 0.00 #_oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.40 _refine_diff_density_max 0.39 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement #_oxford_reflns_threshold_expression_ref I>2.0\s(I) _refine_ls_number_reflns 3247 _refine_ls_number_restraints 1154 _refine_ls_number_parameters 738 #_oxford_refine_ls_R_factor_ref 0.0839 _refine_ls_wR_factor_ref 0.0918 _refine_ls_goodness_of_fit_ref 1.0620 _refine_ls_shift/su_max 0.003161 # The values computed from all data #_oxford_reflns_number_all 4051 _refine_ls_R_factor_all 0.1072 _refine_ls_wR_factor_all 0.1341 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3247 _refine_ls_R_factor_gt 0.0839 _refine_ls_wR_factor_gt 0.0918 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 8.17 -3.11 5.16 ; 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens N11 N -0.0722(19) 0.6827(8) -0.1387(3) 0.028(2) 1.0000 Uiso D U . . . . . O11 O 0.0953(19) 0.6591(13) -0.0860(4) 0.030(3) 1.0000 Uiso D U . . . . . O21 O -0.1081(18) 0.7189(13) -0.0602(3) 0.029(3) 1.0000 Uiso D U . . . . . C121 C 0.0136(15) 0.7748(8) -0.1352(2) 0.028(2) 1.0000 Uiso D U . . . . . C111 C -0.0329(18) 0.8437(10) -0.1207(3) 0.028(3) 1.0000 Uiso D U . . . . . C101 C 0.056(2) 0.9218(10) -0.1242(3) 0.028(3) 1.0000 Uiso D U . . . . . C91 C 0.193(2) 0.9342(10) -0.1420(3) 0.028(3) 1.0000 Uiso D U . . . . . C81 C 0.2511(18) 0.8662(10) -0.1577(3) 0.028(3) 1.0000 Uiso D U . . . . . C71 C 0.1541(16) 0.7789(8) -0.1539(2) 0.028(2) 1.0000 Uiso D U . . . . . C61 C 0.1686(16) 0.6915(8) -0.1689(2) 0.028(2) 1.0000 Uiso D U . . . . . C51 C 0.2715(18) 0.6586(10) -0.1886(3) 0.029(3) 1.0000 Uiso D U . . . . . C41 C 0.239(2) 0.5723(11) -0.1986(3) 0.029(3) 1.0000 Uiso D U . . . . . C31 C 0.099(2) 0.5171(10) -0.1886(3) 0.029(3) 1.0000 Uiso D U . . . . . C21 C -0.0101(18) 0.5469(10) -0.1684(3) 0.029(3) 1.0000 Uiso D U . . . . . C11 C 0.0227(16) 0.6340(8) -0.1584(2) 0.028(2) 1.0000 Uiso D U . . . . . C131 C -0.2161(15) 0.6510(8) -0.1240(2) 0.028(2) 1.0000 Uiso D U . . . . . C141 C -0.2283(15) 0.6489(9) -0.0965(3) 0.028(2) 1.0000 Uiso D U . . . . . C151 C -0.382(2) 0.6125(9) -0.0847(3) 0.029(3) 1.0000 Uiso D U . . . . . C161 C -0.5258(19) 0.5780(9) -0.0976(4) 0.029(3) 1.0000 Uiso D U . . . . . C171 C -0.5218(19) 0.5796(9) -0.1248(4) 0.029(3) 1.0000 Uiso D U . . . . . C181 C -0.3731(19) 0.6151(9) -0.1385(3) 0.029(3) 1.0000 Uiso D U . . . . . C191 C -0.0597(16) 0.6736(15) -0.0825(3) 0.029(3) 1.0000 Uiso D U . . . . . C201 C 0.037(3) 0.749(2) -0.0422(5) 0.030(3) 1.0000 Uiso D U . . . . . N12 N 0.0862(17) 0.2957(8) 0.0026(3) 0.027(2) 1.0000 Uiso D U . . . . . O12 O -0.1154(19) 0.2267(13) -0.0384(3) 0.032(3) 1.0000 Uiso D U . . . . . O22 O 0.0509(18) 0.1797(13) -0.0719(3) 0.030(3) 1.0000 Uiso D U . . . . . C12 C 0.0118(16) 0.3777(8) -0.0061(2) 0.027(2) 1.0000 Uiso D U . . . . . C22 C 0.0732(18) 0.4352(10) -0.0258(3) 0.028(3) 1.0000 Uiso D U . . . . . C32 C -0.019(2) 0.5168(10) -0.0298(3) 0.028(3) 1.0000 Uiso D U . . . . . C42 C -0.169(2) 0.5409(9) -0.0144(3) 0.028(3) 1.0000 Uiso D U . . . . . C52 C -0.2319(18) 0.4835(10) 0.0052(3) 0.028(3) 1.0000 Uiso D U . . . . . C62 C -0.1430(16) 0.4012(8) 0.0097(2) 0.027(2) 1.0000 Uiso D U . . . . . C72 C -0.1664(16) 0.3317(8) 0.0271(2) 0.027(2) 1.0000 Uiso D U . . . . . C82 C -0.2957(18) 0.3096(10) 0.0482(3) 0.028(3) 1.0000 Uiso D U . . . . . C92 C -0.2785(19) 0.2248(12) 0.0608(3) 0.029(3) 1.0000 Uiso D U . . . . . C102 C -0.153(2) 0.1604(10) 0.0555(3) 0.029(3) 1.0000 Uiso D U . . . . . C112 C -0.0262(18) 0.1803(10) 0.0356(3) 0.028(3) 1.0000 Uiso D U . . . . . C122 C -0.0349(16) 0.2612(8) 0.0227(2) 0.027(2) 1.0000 Uiso D U . . . . . C132 C 0.2193(15) 0.2419(8) -0.0090(2) 0.027(2) 1.0000 Uiso D U . . . . . C142 C 0.2110(15) 0.1966(9) -0.0323(2) 0.027(2) 1.0000 Uiso D U . . . . . C152 C 0.357(2) 0.1493(9) -0.0424(3) 0.027(3) 1.0000 Uiso D U . . . . . C162 C 0.5172(19) 0.1450(9) -0.0303(3) 0.027(3) 1.0000 Uiso D U . . . . . C172 C 0.5432(18) 0.1894(10) -0.0065(3) 0.027(3) 1.0000 Uiso D U . . . . . C182 C 0.3918(19) 0.2377(9) 0.0039(3) 0.027(3) 1.0000 Uiso D U . . . . . C192 C 0.0323(17) 0.2011(19) -0.0482(3) 0.030(3) 1.0000 Uiso D U . . . . . C202 C -0.115(3) 0.181(2) -0.0884(4) 0.031(4) 1.0000 Uiso D U . . . . . N13 N 0.5551(19) 0.3690(8) 0.1170(3) 0.029(2) 1.0000 Uiso D U . . . . . O13 O 0.3806(19) 0.4108(13) 0.1669(4) 0.033(3) 1.0000 Uiso D U . . . . . O23 O 0.5826(18) 0.3573(13) 0.1955(3) 0.031(3) 1.0000 Uiso D U . . . . . C13 C 0.4835(16) 0.2812(8) 0.1223(2) 0.030(2) 1.0000 Uiso D U . . . . . C23 C 0.5450(18) 0.2146(10) 0.1395(3) 0.030(3) 1.0000 Uiso D U . . . . . C33 C 0.460(2) 0.1297(10) 0.1389(3) 0.031(3) 1.0000 Uiso D U . . . . . C43 C 0.318(2) 0.1115(10) 0.1217(3) 0.031(3) 1.0000 Uiso D U . . . . . C53 C 0.2553(18) 0.1774(10) 0.1048(3) 0.030(3) 1.0000 Uiso D U . . . . . C63 C 0.3344(16) 0.2625(8) 0.1046(2) 0.030(2) 1.0000 Uiso D U . . . . . C73 C 0.3138(16) 0.3422(8) 0.0888(2) 0.030(2) 1.0000 Uiso D U . . . . . C83 C 0.2046(18) 0.3685(10) 0.0679(3) 0.031(3) 1.0000 Uiso D U . . . . . C93 C 0.237(2) 0.4538(11) 0.0554(3) 0.031(3) 1.0000 Uiso D U . . . . . C103 C 0.372(2) 0.5114(10) 0.0632(3) 0.031(3) 1.0000 Uiso D U . . . . . C113 C 0.4887(18) 0.4897(9) 0.0842(3) 0.030(3) 1.0000 Uiso D U . . . . . C123 C 0.4585(16) 0.4060(8) 0.0967(2) 0.030(2) 1.0000 Uiso D U . . . . . C133 C 0.7080(15) 0.4081(8) 0.1303(2) 0.029(2) 1.0000 Uiso D U . . . . . C143 C 0.7003(15) 0.4211(9) 0.1568(2) 0.029(2) 1.0000 Uiso D U . . . . . C153 C 0.857(2) 0.4631(9) 0.1688(3) 0.029(3) 1.0000 Uiso D U . . . . . C163 C 1.0045(19) 0.4891(9) 0.1564(4) 0.028(3) 1.0000 Uiso D U . . . . . C173 C 1.0092(18) 0.4742(9) 0.1281(4) 0.028(3) 1.0000 Uiso D U . . . . . C183 C 0.867(2) 0.4351(9) 0.1151(3) 0.028(3) 1.0000 Uiso D U . . . . . C193 C 0.5433(15) 0.3983(15) 0.1722(3) 0.031(3) 1.0000 Uiso D U . . . . . C203 C 0.432(3) 0.329(2) 0.2122(5) 0.033(4) 1.0000 Uiso D U . . . . . N14 N -0.0694(19) 0.2073(8) 0.2574(3) 0.028(2) 1.0000 Uiso D U . . . . . O14 O 0.1097(19) 0.1704(13) 0.2082(3) 0.031(3) 1.0000 Uiso D U . . . . . O24 O -0.0925(17) 0.2171(13) 0.1766(3) 0.031(3) 1.0000 Uiso D U . . . . . C124 C 0.0101(16) 0.2910(8) 0.2537(2) 0.028(2) 1.0000 Uiso D U . . . . . C114 C -0.0454(18) 0.3659(10) 0.2356(3) 0.028(3) 1.0000 Uiso D U . . . . . C104 C 0.052(2) 0.4519(10) 0.2379(3) 0.029(3) 1.0000 Uiso D U . . . . . C94 C 0.193(2) 0.4622(10) 0.2566(3) 0.029(3) 1.0000 Uiso D U . . . . . C84 C 0.2369(18) 0.3860(10) 0.2727(3) 0.029(3) 1.0000 Uiso D U . . . . . C74 C 0.1545(16) 0.3046(8) 0.2721(2) 0.028(2) 1.0000 Uiso D U . . . . . C64 C 0.1568(16) 0.2201(8) 0.2860(2) 0.028(2) 1.0000 Uiso D U . . . . . C54 C 0.2775(18) 0.1883(10) 0.3069(3) 0.028(3) 1.0000 Uiso D U . . . . . C44 C 0.2521(19) 0.1003(11) 0.3162(3) 0.028(3) 1.0000 Uiso D U . . . . . C34 C 0.116(2) 0.0429(10) 0.3063(3) 0.028(3) 1.0000 Uiso D U . . . . . C24 C -0.0005(18) 0.0730(9) 0.2865(3) 0.028(3) 1.0000 Uiso D U . . . . . C14 C 0.0247(16) 0.1618(8) 0.2770(2) 0.028(2) 1.0000 Uiso D U . . . . . C134 C -0.2310(15) 0.1704(8) 0.2428(2) 0.028(2) 1.0000 Uiso D U . . . . . C144 C -0.2108(15) 0.1550(9) 0.2166(3) 0.029(2) 1.0000 Uiso D U . . . . . C154 C -0.360(2) 0.1173(9) 0.2025(3) 0.029(3) 1.0000 Uiso D U . . . . . C164 C -0.5210(19) 0.0957(9) 0.2170(4) 0.029(3) 1.0000 Uiso D U . . . . . C174 C -0.5343(18) 0.1105(9) 0.2430(4) 0.029(3) 1.0000 Uiso D U . . . . . C184 C -0.3855(19) 0.1477(9) 0.2560(3) 0.028(3) 1.0000 Uiso D U . . . . . C194 C -0.0468(15) 0.1821(15) 0.1998(3) 0.030(3) 1.0000 Uiso D U . . . . . C204 C 0.056(3) 0.250(2) 0.1614(4) 0.032(4) 1.0000 Uiso D U . . . . . N15 N 0.0412(19) 0.1189(8) 0.5011(3) 0.027(2) 1.0000 Uiso D U . . . . . O15 O -0.1292(19) 0.0954(13) 0.4504(4) 0.029(3) 1.0000 Uiso D U . . . . . O25 O 0.0796(18) 0.1552(13) 0.4221(3) 0.030(3) 1.0000 Uiso D U . . . . . C15 C -0.0442(15) 0.2043(8) 0.4978(2) 0.027(2) 1.0000 Uiso D U . . . . . C25 C 0.0067(18) 0.2779(10) 0.4819(3) 0.027(3) 1.0000 Uiso D U . . . . . C35 C -0.086(2) 0.3602(10) 0.4850(3) 0.028(3) 1.0000 Uiso D U . . . . . C45 C -0.224(2) 0.3695(10) 0.5035(3) 0.028(3) 1.0000 Uiso D U . . . . . C55 C -0.2764(17) 0.2967(10) 0.5189(3) 0.028(3) 1.0000 Uiso D U . . . . . C65 C -0.1816(16) 0.2101(8) 0.5157(2) 0.027(2) 1.0000 Uiso D U . . . . . C75 C -0.1890(16) 0.1231(8) 0.5303(2) 0.027(2) 1.0000 Uiso D U . . . . . C85 C -0.3050(18) 0.0936(10) 0.5504(3) 0.028(3) 1.0000 Uiso D U . . . . . C95 C -0.281(2) 0.0138(12) 0.5609(3) 0.029(3) 1.0000 Uiso D U . . . . . C105 C -0.134(2) -0.0464(10) 0.5513(3) 0.028(3) 1.0000 Uiso D U . . . . . C115 C -0.0219(18) -0.0162(10) 0.5315(3) 0.028(3) 1.0000 Uiso D U . . . . . C125 C -0.0526(16) 0.0687(8) 0.5212(2) 0.027(2) 1.0000 Uiso D U . . . . . C135 C 0.1909(15) 0.0811(8) 0.4866(2) 0.027(2) 1.0000 Uiso D U . . . . . C145 C 0.1933(15) 0.0793(9) 0.4588(2) 0.027(2) 1.0000 Uiso D U . . . . . C155 C 0.340(2) 0.0485(9) 0.4457(3) 0.028(3) 1.0000 Uiso D U . . . . . C165 C 0.4938(18) 0.0174(9) 0.4608(4) 0.028(3) 1.0000 Uiso D U . . . . . C175 C 0.4947(18) 0.0189(9) 0.4862(4) 0.028(3) 1.0000 Uiso D U . . . . . C185 C 0.337(2) 0.0520(9) 0.4991(3) 0.028(3) 1.0000 Uiso D U . . . . . C195 C 0.0215(15) 0.1101(15) 0.4424(3) 0.028(3) 1.0000 Uiso D U . . . . . C205 C -0.065(3) 0.190(2) 0.4051(5) 0.031(3) 1.0000 Uiso D U . . . . . N16 N 0.5465(18) 0.2279(8) 0.6041(3) 0.027(2) 1.0000 Uiso D U . . . . . O16 O 0.3727(19) 0.2755(13) 0.6495(3) 0.033(3) 1.0000 Uiso D U . . . . . O26 O 0.5449(18) 0.3071(14) 0.6841(3) 0.032(3) 1.0000 Uiso D U . . . . . C16 C 0.4699(15) 0.1407(8) 0.6092(2) 0.028(2) 1.0000 Uiso D U . . . . . C26 C 0.5194(18) 0.0748(10) 0.6275(3) 0.029(3) 1.0000 Uiso D U . . . . . C36 C 0.423(2) -0.0076(10) 0.6275(3) 0.030(3) 1.0000 Uiso D U . . . . . C46 C 0.282(2) -0.0237(10) 0.6100(3) 0.030(3) 1.0000 Uiso D U . . . . . C56 C 0.2318(18) 0.0405(10) 0.5921(3) 0.029(3) 1.0000 Uiso D U . . . . . C66 C 0.3265(16) 0.1256(8) 0.5915(2) 0.028(2) 1.0000 Uiso D U . . . . . C76 C 0.3131(16) 0.2135(8) 0.5749(2) 0.028(2) 1.0000 Uiso D U . . . . . C86 C 0.2010(18) 0.2439(10) 0.5554(3) 0.029(3) 1.0000 Uiso D U . . . . . C96 C 0.217(2) 0.3295(12) 0.5456(3) 0.030(3) 1.0000 Uiso D U . . . . . C106 C 0.355(2) 0.3865(10) 0.5568(3) 0.030(3) 1.0000 Uiso D U . . . . . C116 C 0.4717(18) 0.3605(10) 0.5766(3) 0.029(3) 1.0000 Uiso D U . . . . . C126 C 0.4490(16) 0.2708(8) 0.5858(2) 0.028(2) 1.0000 Uiso D U . . . . . C136 C 0.7139(15) 0.2633(8) 0.6171(2) 0.027(2) 1.0000 Uiso D U . . . . . C146 C 0.6863(15) 0.2972(9) 0.6440(2) 0.028(2) 1.0000 Uiso D U . . . . . C156 C 0.8429(19) 0.3424(9) 0.6541(3) 0.027(3) 1.0000 Uiso D U . . . . . C166 C 1.0051(19) 0.3539(9) 0.6389(3) 0.027(3) 1.0000 Uiso D U . . . . . C176 C 1.0107(18) 0.3177(10) 0.6142(3) 0.026(3) 1.0000 Uiso D U . . . . . C186 C 0.8686(19) 0.2738(9) 0.6033(3) 0.026(3) 1.0000 Uiso D U . . . . . C196 C 0.5152(16) 0.2913(19) 0.6573(3) 0.030(3) 1.0000 Uiso D U . . . . . C206 C 0.382(3) 0.302(2) 0.7002(4) 0.032(4) 1.0000 Uiso D U . . . . . N17 N -0.1180(18) 0.1990(8) 0.7477(3) 0.027(2) 1.0000 Uiso D U . . . . . O17 O 0.0607(19) 0.1433(13) 0.7038(3) 0.033(3) 1.0000 Uiso D U . . . . . O27 O -0.1124(18) 0.1026(14) 0.6699(3) 0.033(3) 1.0000 Uiso D U . . . . . C17 C -0.0091(16) 0.1635(8) 0.7678(2) 0.027(2) 1.0000 Uiso D U . . . . . C27 C -0.0238(18) 0.0808(9) 0.7811(3) 0.026(3) 1.0000 Uiso D U . . . . . C37 C 0.100(2) 0.0636(10) 0.8008(3) 0.027(3) 1.0000 Uiso D U . . . . . C47 C 0.2344(19) 0.1277(11) 0.8073(3) 0.027(3) 1.0000 Uiso D U . . . . . C57 C 0.2493(17) 0.2100(10) 0.7942(3) 0.027(3) 1.0000 Uiso D U . . . . . C67 C 0.1318(16) 0.2303(8) 0.7747(2) 0.027(2) 1.0000 Uiso D U . . . . . C77 C 0.1032(16) 0.3078(8) 0.7571(2) 0.028(2) 1.0000 Uiso D U . . . . . C87 C 0.1805(18) 0.3929(10) 0.7536(3) 0.029(3) 1.0000 Uiso D U . . . . . C97 C 0.121(2) 0.4532(9) 0.7356(3) 0.029(3) 1.0000 Uiso D U . . . . . C107 C -0.030(2) 0.4302(10) 0.7187(3) 0.030(3) 1.0000 Uiso D U . . . . . C117 C -0.1206(18) 0.3448(10) 0.7208(3) 0.029(3) 1.0000 Uiso D U . . . . . C127 C -0.0460(16) 0.2858(8) 0.7407(2) 0.028(2) 1.0000 Uiso D U . . . . . C137 C -0.2630(15) 0.1457(8) 0.7352(2) 0.028(2) 1.0000 Uiso D U . . . . . C147 C -0.2551(15) 0.1149(9) 0.7099(2) 0.029(2) 1.0000 Uiso D U . . . . . C157 C -0.4122(19) 0.0729(9) 0.6999(3) 0.029(3) 1.0000 Uiso D U . . . . . C167 C -0.5639(19) 0.0649(9) 0.7149(4) 0.029(3) 1.0000 Uiso D U . . . . . C177 C -0.5762(18) 0.0937(10) 0.7395(4) 0.029(3) 1.0000 Uiso D U . . . . . C187 C -0.4246(19) 0.1360(9) 0.7503(3) 0.028(3) 1.0000 Uiso D U . . . . . C197 C -0.0761(17) 0.1230(19) 0.6954(3) 0.031(3) 1.0000 Uiso D U . . . . . C207 C 0.051(3) 0.116(2) 0.6530(4) 0.034(4) 1.0000 Uiso D U . . . . . N18 N 0.3799(17) 0.2702(8) 0.8607(3) 0.025(2) 1.0000 Uiso D U . . . . . O18 O 0.5716(19) 0.3332(13) 0.9036(3) 0.029(3) 1.0000 Uiso D U . . . . . O28 O 0.4109(18) 0.3871(13) 0.9363(3) 0.029(3) 1.0000 Uiso D U . . . . . C18 C 0.4920(16) 0.3051(8) 0.8414(2) 0.025(2) 1.0000 Uiso D U . . . . . C28 C 0.4790(18) 0.3872(9) 0.8280(3) 0.026(3) 1.0000 Uiso D U . . . . . C38 C 0.604(2) 0.4036(10) 0.8086(3) 0.027(3) 1.0000 Uiso D U . . . . . C48 C 0.7395(19) 0.3388(11) 0.8025(3) 0.027(3) 1.0000 Uiso D U . . . . . C58 C 0.7532(18) 0.2571(10) 0.8157(3) 0.026(3) 1.0000 Uiso D U . . . . . C68 C 0.6226(16) 0.2401(8) 0.8363(2) 0.025(2) 1.0000 Uiso D U . . . . . C78 C 0.6008(16) 0.1656(8) 0.8548(2) 0.025(2) 1.0000 Uiso D U . . . . . C88 C 0.6966(18) 0.0804(10) 0.8590(3) 0.025(3) 1.0000 Uiso D U . . . . . C98 C 0.626(2) 0.0233(9) 0.8790(3) 0.025(3) 1.0000 Uiso D U . . . . . C108 C 0.476(2) 0.0492(10) 0.8930(3) 0.026(3) 1.0000 Uiso D U . . . . . C118 C 0.3874(17) 0.1307(10) 0.8884(3) 0.025(3) 1.0000 Uiso D U . . . . . C128 C 0.4483(15) 0.1875(8) 0.8696(2) 0.025(2) 1.0000 Uiso D U . . . . . C138 C 0.2259(15) 0.3168(8) 0.8726(2) 0.025(2) 1.0000 Uiso D U . . . . . C148 C 0.2511(15) 0.3641(9) 0.8960(2) 0.025(2) 1.0000 Uiso D U . . . . . C158 C 0.1050(19) 0.4166(9) 0.9064(3) 0.025(3) 1.0000 Uiso D U . . . . . C168 C -0.0644(19) 0.4221(9) 0.8934(3) 0.025(3) 1.0000 Uiso D U . . . . . C178 C -0.0792(18) 0.3719(10) 0.8695(3) 0.026(3) 1.0000 Uiso D U . . . . . C188 C 0.0675(19) 0.3209(9) 0.8597(3) 0.025(3) 1.0000 Uiso D U . . . . . C198 C 0.4229(16) 0.3636(17) 0.9115(3) 0.027(2) 1.0000 Uiso D U . . . . . C208 C 0.569(3) 0.390(2) 0.9519(4) 0.030(3) 1.0000 Uiso D U . . . . . H1111 H -0.1273 0.8379 -0.1079 0.0320 1.0000 Uiso R . . . . . . H1011 H 0.0236 0.9739 -0.1137 0.0392 1.0000 Uiso R . . . . . . H911 H 0.2540 0.9922 -0.1441 0.0342 1.0000 Uiso R . . . . . . H811 H 0.3468 0.8734 -0.1703 0.0259 1.0000 Uiso R . . . . . . H511 H 0.3677 0.6952 -0.1959 0.0418 1.0000 Uiso R . . . . . . H411 H 0.3085 0.5466 -0.2126 0.0463 1.0000 Uiso R . . . . . . H311 H 0.0777 0.4569 -0.1956 0.0457 1.0000 Uiso R . . . . . . H211 H -0.1061 0.5089 -0.1617 0.0310 1.0000 Uiso R . . . . . . H1511 H -0.3853 0.6110 -0.0660 0.0302 1.0000 Uiso R . . . . . . H1611 H -0.6290 0.5535 -0.0884 0.0276 1.0000 Uiso R . . . . . . H1711 H -0.6245 0.5568 -0.1344 0.0250 1.0000 Uiso R . . . . . . H1811 H -0.3730 0.6162 -0.1572 0.0319 1.0000 Uiso R . . . . . . H2011 H -0.0188 0.7799 -0.0271 0.0537 1.0000 Uiso R . . . . . . H2012 H 0.1171 0.7925 -0.0516 0.0537 1.0000 Uiso R . . . . . . H2013 H 0.1101 0.6958 -0.0362 0.0537 1.0000 Uiso R . . . . . . H221 H 0.1761 0.4186 -0.0364 0.0414 1.0000 Uiso R . . . . . . H321 H 0.0203 0.5574 -0.0434 0.0468 1.0000 Uiso R . . . . . . H421 H -0.2304 0.5980 -0.0177 0.0477 1.0000 Uiso R . . . . . . H521 H -0.3354 0.5009 0.0155 0.0389 1.0000 Uiso R . . . . . . H821 H -0.3895 0.3522 0.0530 0.0253 1.0000 Uiso R . . . . . . H921 H -0.3635 0.2119 0.0745 0.0292 1.0000 Uiso R . . . . . . H1021 H -0.1486 0.1038 0.0651 0.0360 1.0000 Uiso R . . . . . . H1121 H 0.0663 0.1362 0.0313 0.0320 1.0000 Uiso R . . . . . . H1521 H 0.3431 0.1184 -0.0588 0.0343 1.0000 Uiso R . . . . . . H1621 H 0.6158 0.1112 -0.0380 0.0295 1.0000 Uiso R . . . . . . H1721 H 0.6578 0.1873 0.0024 0.0269 1.0000 Uiso R . . . . . . H1821 H 0.4051 0.2687 0.0203 0.0308 1.0000 Uiso R . . . . . . H2021 H -0.0820 0.1628 -0.1064 0.0452 1.0000 Uiso R . . . . . . H2022 H -0.1684 0.2436 -0.0886 0.0452 1.0000 Uiso R . . . . . . H2023 H -0.2041 0.1373 -0.0812 0.0452 1.0000 Uiso R . . . . . . H231 H 0.6427 0.2270 0.1514 0.0405 1.0000 Uiso R . . . . . . H331 H 0.4991 0.0826 0.1507 0.0446 1.0000 Uiso R . . . . . . H431 H 0.2631 0.0516 0.1215 0.0482 1.0000 Uiso R . . . . . . H531 H 0.1569 0.1637 0.0931 0.0359 1.0000 Uiso R . . . . . . H831 H 0.1077 0.3295 0.0620 0.0343 1.0000 Uiso R . . . . . . H931 H 0.1615 0.4717 0.0411 0.0439 1.0000 Uiso R . . . . . . H1031 H 0.3890 0.5686 0.0543 0.0379 1.0000 Uiso R . . . . . . H1131 H 0.5842 0.5304 0.0896 0.0365 1.0000 Uiso R . . . . . . H1531 H 0.8528 0.4728 0.1873 0.0377 1.0000 Uiso R . . . . . . H1631 H 1.1051 0.5166 0.1654 0.0290 1.0000 Uiso R . . . . . . H1731 H 1.1152 0.4927 0.1185 0.0260 1.0000 Uiso R . . . . . . H1831 H 0.8716 0.4258 0.0966 0.0321 1.0000 Uiso R . . . . . . H2031 H 0.4805 0.3004 0.2283 0.0537 1.0000 Uiso R . . . . . . H2032 H 0.3558 0.3825 0.2168 0.0537 1.0000 Uiso R . . . . . . H2033 H 0.3580 0.2835 0.2026 0.0537 1.0000 Uiso R . . . . . . H1141 H -0.1413 0.3578 0.2231 0.0308 1.0000 Uiso R . . . . . . H1041 H 0.0196 0.5019 0.2267 0.0402 1.0000 Uiso R . . . . . . H941 H 0.2545 0.5204 0.2577 0.0383 1.0000 Uiso R . . . . . . H841 H 0.3336 0.3943 0.2851 0.0380 1.0000 Uiso R . . . . . . H541 H 0.3714 0.2275 0.3136 0.0340 1.0000 Uiso R . . . . . . H441 H 0.3325 0.0807 0.3299 0.0398 1.0000 Uiso R . . . . . . H341 H 0.1031 -0.0179 0.3133 0.0416 1.0000 Uiso R . . . . . . H241 H -0.0943 0.0339 0.2796 0.0365 1.0000 Uiso R . . . . . . H1541 H -0.3533 0.1071 0.1840 0.0407 1.0000 Uiso R . . . . . . H1641 H -0.6234 0.0698 0.2080 0.0347 1.0000 Uiso R . . . . . . H1741 H -0.6438 0.0953 0.2523 0.0311 1.0000 Uiso R . . . . . . H1841 H -0.3920 0.1581 0.2744 0.0351 1.0000 Uiso R . . . . . . H2041 H 0.0096 0.2737 0.1446 0.0489 1.0000 Uiso R . . . . . . H2042 H 0.1183 0.2995 0.1710 0.0489 1.0000 Uiso R . . . . . . H2043 H 0.1433 0.1992 0.1580 0.0489 1.0000 Uiso R . . . . . . H251 H 0.1027 0.2718 0.4693 0.0360 1.0000 Uiso R . . . . . . H351 H -0.0530 0.4119 0.4744 0.0523 1.0000 Uiso R . . . . . . H451 H -0.2849 0.4275 0.5054 0.0459 1.0000 Uiso R . . . . . . H551 H -0.3735 0.3029 0.5314 0.0319 1.0000 Uiso R . . . . . . H851 H -0.4010 0.1331 0.5564 0.0361 1.0000 Uiso R . . . . . . H951 H -0.3594 -0.0060 0.5748 0.0447 1.0000 Uiso R . . . . . . H1051 H -0.1163 -0.1059 0.5589 0.0530 1.0000 Uiso R . . . . . . H1151 H 0.0750 -0.0543 0.5251 0.0448 1.0000 Uiso R . . . . . . H1551 H 0.3428 0.0473 0.4271 0.0385 1.0000 Uiso R . . . . . . H1651 H 0.5995 -0.0053 0.4519 0.0378 1.0000 Uiso R . . . . . . H1751 H 0.5985 -0.0017 0.4960 0.0314 1.0000 Uiso R . . . . . . H1851 H 0.3355 0.0531 0.5178 0.0395 1.0000 Uiso R . . . . . . H2051 H -0.0097 0.2243 0.3904 0.0485 1.0000 Uiso R . . . . . . H2052 H -0.1479 0.2313 0.4148 0.0485 1.0000 Uiso R . . . . . . H2053 H -0.1347 0.1371 0.3983 0.0485 1.0000 Uiso R . . . . . . H261 H 0.6167 0.0856 0.6396 0.0394 1.0000 Uiso R . . . . . . H361 H 0.4548 -0.0543 0.6399 0.0473 1.0000 Uiso R . . . . . . H461 H 0.2187 -0.0814 0.6105 0.0521 1.0000 Uiso R . . . . . . H561 H 0.1339 0.0286 0.5802 0.0418 1.0000 Uiso R . . . . . . H861 H 0.1091 0.2036 0.5487 0.0318 1.0000 Uiso R . . . . . . H961 H 0.1401 0.3509 0.5318 0.0445 1.0000 Uiso R . . . . . . H1061 H 0.3679 0.4476 0.5501 0.0439 1.0000 Uiso R . . . . . . H1161 H 0.5623 0.4013 0.5835 0.0336 1.0000 Uiso R . . . . . . H1561 H 0.8391 0.3668 0.6714 0.0267 1.0000 Uiso R . . . . . . H1661 H 1.1086 0.3856 0.6459 0.0286 1.0000 Uiso R . . . . . . H1761 H 1.1211 0.3239 0.6043 0.0263 1.0000 Uiso R . . . . . . H1861 H 0.8774 0.2501 0.5859 0.0271 1.0000 Uiso R . . . . . . H2061 H 0.4147 0.3145 0.7185 0.0366 1.0000 Uiso R . . . . . . H2062 H 0.3269 0.2397 0.6989 0.0366 1.0000 Uiso R . . . . . . H2063 H 0.2925 0.3481 0.6941 0.0366 1.0000 Uiso R . . . . . . H271 H -0.1162 0.0368 0.7767 0.0393 1.0000 Uiso R . . . . . . H371 H 0.0937 0.0068 0.8102 0.0383 1.0000 Uiso R . . . . . . H471 H 0.3178 0.1141 0.8211 0.0435 1.0000 Uiso R . . . . . . H571 H 0.3429 0.2529 0.7990 0.0381 1.0000 Uiso R . . . . . . H871 H 0.2829 0.4096 0.7642 0.0430 1.0000 Uiso R . . . . . . H971 H 0.1794 0.5119 0.7340 0.0456 1.0000 Uiso R . . . . . . H1071 H -0.0696 0.4740 0.7059 0.0529 1.0000 Uiso R . . . . . . H1171 H -0.2223 0.3281 0.7100 0.0448 1.0000 Uiso R . . . . . . H1571 H -0.4126 0.0502 0.6824 0.0326 1.0000 Uiso R . . . . . . H1671 H -0.6687 0.0359 0.7073 0.0301 1.0000 Uiso R . . . . . . H1771 H -0.6866 0.0859 0.7492 0.0305 1.0000 Uiso R . . . . . . H1871 H -0.4287 0.1581 0.7679 0.0345 1.0000 Uiso R . . . . . . H2071 H 0.0179 0.1011 0.6348 0.0535 1.0000 Uiso R . . . . . . H2072 H 0.1475 0.0736 0.6590 0.0535 1.0000 Uiso R . . . . . . H2073 H 0.0956 0.1800 0.6539 0.0535 1.0000 Uiso R . . . . . . H281 H 0.3863 0.4313 0.8322 0.0390 1.0000 Uiso R . . . . . . H381 H 0.5987 0.4604 0.7992 0.0561 1.0000 Uiso R . . . . . . H481 H 0.8242 0.3520 0.7887 0.0492 1.0000 Uiso R . . . . . . H581 H 0.8460 0.2131 0.8115 0.0412 1.0000 Uiso R . . . . . . H881 H 0.8017 0.0634 0.8490 0.0366 1.0000 Uiso R . . . . . . H981 H 0.6838 -0.0343 0.8827 0.0475 1.0000 Uiso R . . . . . . H1081 H 0.4319 0.0094 0.9065 0.0512 1.0000 Uiso R . . . . . . H1181 H 0.2828 0.1472 0.8986 0.0412 1.0000 Uiso R . . . . . . H1581 H 0.1217 0.4487 0.9225 0.0305 1.0000 Uiso R . . . . . . H1681 H -0.1637 0.4576 0.9002 0.0311 1.0000 Uiso R . . . . . . H1781 H -0.1918 0.3736 0.8600 0.0281 1.0000 Uiso R . . . . . . H1881 H 0.0541 0.2887 0.8435 0.0327 1.0000 Uiso R . . . . . . H2081 H 0.5362 0.4085 0.9698 0.0583 1.0000 Uiso R . . . . . . H2082 H 0.6239 0.3274 0.9523 0.0583 1.0000 Uiso R . . . . . . H2083 H 0.6575 0.4337 0.9445 0.0583 1.0000 Uiso R . . . . . . _refine_ls_extinction_method None #_oxford_refine_ls_scale 1.037(5) #loop_ # _oxford_twin_element_scale_factors # 0.810(5) # 0.190(5) 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 N11 . C121 . 1.477(11) yes N11 . C11 . 1.400(11) yes N11 . C131 . 1.365(11) yes O11 . C191 . 1.158(12) yes O21 . C191 . 1.356(12) yes O21 . C201 . 1.461(13) yes C121 . C111 . 1.282(12) yes C121 . C71 . 1.396(11) yes C111 . C101 . 1.308(12) yes C111 . H1111 . 0.950 no C101 . C91 . 1.360(13) yes C101 . H1011 . 0.950 no C91 . C81 . 1.332(13) yes C91 . H911 . 0.950 no C81 . C71 . 1.455(12) yes C81 . H811 . 0.950 no C71 . C61 . 1.474(11) yes C61 . C51 . 1.338(12) yes C61 . C11 . 1.448(11) yes C51 . C41 . 1.363(12) yes C51 . H511 . 0.950 no C41 . C31 . 1.384(13) yes C41 . H411 . 0.950 no C31 . C21 . 1.365(12) yes C31 . H311 . 0.950 no C21 . C11 . 1.376(12) yes C21 . H211 . 0.950 no C131 . C141 . 1.402(12) yes C131 . C181 . 1.454(12) yes C141 . C151 . 1.369(12) yes C141 . C191 . 1.460(12) yes C151 . C161 . 1.330(12) yes C151 . H1511 . 0.950 no C161 . C171 . 1.387(13) yes C161 . H1611 . 0.950 no C171 . C181 . 1.382(13) yes C171 . H1711 . 0.950 no C181 . H1811 . 0.950 no C201 . H2011 . 0.980 no C201 . H2012 . 0.980 no C201 . H2013 . 0.980 no N12 . C12 . 1.373(11) yes N12 . C122 . 1.439(11) yes N12 . C132 . 1.371(11) yes O12 . C192 . 1.240(12) yes O22 . C192 . 1.251(12) yes O22 . C202 . 1.464(13) yes C12 . C22 . 1.374(12) yes C12 . C62 . 1.425(11) yes C22 . C32 . 1.368(12) yes C22 . H221 . 0.950 no C32 . C42 . 1.385(12) yes C32 . H321 . 0.950 no C42 . C52 . 1.373(13) yes C42 . H421 . 0.950 no C52 . C62 . 1.370(12) yes C52 . H521 . 0.950 no C62 . C72 . 1.346(11) yes C72 . C82 . 1.459(12) yes C72 . C122 . 1.412(11) yes C82 . C92 . 1.386(13) yes C82 . H821 . 0.950 no C92 . C102 . 1.328(13) yes C92 . H921 . 0.950 no C102 . C112 . 1.395(12) yes C102 . H1021 . 0.950 no C112 . C122 . 1.340(12) yes C112 . H1121 . 0.950 no C132 . C142 . 1.352(12) yes C132 . C182 . 1.416(12) yes C142 . C152 . 1.360(12) yes C142 . C192 . 1.533(12) yes C152 . C162 . 1.318(12) yes C152 . H1521 . 0.950 no C162 . C172 . 1.380(13) yes C162 . H1621 . 0.950 no C172 . C182 . 1.406(12) yes C172 . H1721 . 0.950 no C182 . H1821 . 0.950 no C202 . H2021 . 0.980 no C202 . H2022 . 0.980 no C202 . H2023 . 0.980 no N13 . C13 . 1.395(11) yes N13 . C123 . 1.356(11) yes N13 . C133 . 1.418(11) yes O13 . C193 . 1.225(12) yes O23 . C193 . 1.354(12) yes O23 . C203 . 1.442(13) yes C13 . C23 . 1.371(12) yes C13 . C63 . 1.435(11) yes C23 . C33 . 1.371(12) yes C23 . H231 . 0.950 no C33 . C43 . 1.381(13) yes C33 . H331 . 0.950 no C43 . C53 . 1.358(13) yes C43 . H431 . 0.950 no C53 . C63 . 1.354(12) yes C53 . H531 . 0.950 no C63 . C73 . 1.409(11) yes C73 . C83 . 1.380(12) yes C73 . C123 . 1.453(11) yes C83 . C93 . 1.404(13) yes C83 . H831 . 0.950 no C93 . C103 . 1.344(12) yes C93 . H931 . 0.950 no C103 . C113 . 1.396(12) yes C103 . H1031 . 0.950 no C113 . C123 . 1.381(12) yes C113 . H1131 . 0.950 no C133 . C143 . 1.365(12) yes C133 . C183 . 1.443(12) yes C143 . C153 . 1.424(12) yes C143 . C193 . 1.420(12) yes C153 . C163 . 1.301(12) yes C153 . H1531 . 0.950 no C163 . C173 . 1.456(13) yes C163 . H1631 . 0.950 no C173 . C183 . 1.348(12) yes C173 . H1731 . 0.950 no C183 . H1831 . 0.950 no C203 . H2031 . 0.980 no C203 . H2032 . 0.980 no C203 . H2033 . 0.980 no N14 . C124 . 1.350(11) yes N14 . C14 . 1.377(11) yes N14 . C134 . 1.486(11) yes O14 . C194 . 1.226(12) yes O24 . C194 . 1.322(12) yes O24 . C204 . 1.409(13) yes C124 . C114 . 1.475(12) yes C124 . C74 . 1.419(11) yes C114 . C104 . 1.432(12) yes C114 . H1141 . 0.950 no C104 . C94 . 1.407(13) yes C104 . H1041 . 0.950 no C94 . C84 . 1.405(13) yes C94 . H941 . 0.950 no C84 . C74 . 1.317(12) yes C84 . H841 . 0.950 no C74 . C64 . 1.407(11) yes C64 . C54 . 1.454(12) yes C64 . C14 . 1.355(11) yes C54 . C44 . 1.366(12) yes C54 . H541 . 0.950 no C44 . C34 . 1.387(13) yes C44 . H441 . 0.950 no C34 . C24 . 1.383(12) yes C34 . H341 . 0.950 no C24 . C14 . 1.380(12) yes C24 . H241 . 0.950 no C134 . C144 . 1.359(12) yes C134 . C184 . 1.347(12) yes C144 . C154 . 1.409(12) yes C144 . C194 . 1.517(12) yes C154 . C164 . 1.416(13) yes C154 . H1541 . 0.950 no C164 . C174 . 1.345(13) yes C164 . H1641 . 0.950 no C174 . C184 . 1.375(12) yes C174 . H1741 . 0.950 no C184 . H1841 . 0.950 no C204 . H2041 . 0.980 no C204 . H2042 . 0.980 no C204 . H2043 . 0.980 no N15 . C15 . 1.389(11) yes N15 . C125 . 1.422(11) yes N15 . C135 . 1.423(11) yes O15 . C195 . 1.186(12) yes O25 . C195 . 1.293(12) yes O25 . C205 . 1.451(13) yes C15 . C25 . 1.382(12) yes C15 . C65 . 1.353(11) yes C25 . C35 . 1.372(12) yes C25 . H251 . 0.950 no C35 . C45 . 1.384(13) yes C35 . H351 . 0.950 no C45 . C55 . 1.363(13) yes C45 . H451 . 0.950 no C55 . C65 . 1.436(12) yes C55 . H551 . 0.950 no C65 . C75 . 1.459(11) yes C75 . C85 . 1.391(12) yes C75 . C125 . 1.346(11) yes C85 . C95 . 1.279(12) yes C85 . H851 . 0.950 no C95 . C105 . 1.460(12) yes C95 . H951 . 0.950 no C105 . C115 . 1.367(12) yes C105 . H1051 . 0.950 no C115 . C125 . 1.350(12) yes C115 . H1151 . 0.950 no C135 . C145 . 1.415(12) yes C135 . C185 . 1.306(12) yes C145 . C155 . 1.331(12) yes C145 . C195 . 1.563(12) yes C155 . C165 . 1.425(12) yes C155 . H1551 . 0.950 no C165 . C175 . 1.295(13) yes C165 . H1651 . 0.950 no C175 . C185 . 1.402(12) yes C175 . H1751 . 0.950 no C185 . H1851 . 0.950 no C205 . H2051 . 0.980 no C205 . H2052 . 0.980 no C205 . H2053 . 0.980 no N16 . C16 . 1.399(11) yes N16 . C126 . 1.325(11) yes N16 . C136 . 1.475(11) yes O16 . C196 . 1.131(12) yes O26 . C196 . 1.400(12) yes O26 . C206 . 1.442(13) yes C16 . C26 . 1.377(12) yes C16 . C66 . 1.394(11) yes C26 . C36 . 1.377(12) yes C26 . H261 . 0.950 no C36 . C46 . 1.377(13) yes C36 . H361 . 0.950 no C46 . C56 . 1.347(13) yes C46 . H461 . 0.950 no C56 . C66 . 1.406(12) yes C56 . H561 . 0.950 no C66 . C76 . 1.524(11) yes C76 . C86 . 1.356(12) yes C76 . C126 . 1.401(11) yes C86 . C96 . 1.335(12) yes C86 . H861 . 0.950 no C96 . C106 . 1.417(13) yes C96 . H961 . 0.950 no C106 . C116 . 1.366(12) yes C106 . H1061 . 0.950 no C116 . C126 . 1.384(12) yes C116 . H1161 . 0.950 no C136 . C146 . 1.466(12) yes C136 . C186 . 1.334(12) yes C146 . C156 . 1.406(12) yes C146 . C196 . 1.416(12) yes C156 . C166 . 1.418(12) yes C156 . H1561 . 0.950 no C166 . C176 . 1.360(13) yes C166 . H1661 . 0.950 no C176 . C186 . 1.332(12) yes C176 . H1761 . 0.950 no C186 . H1861 . 0.950 no C206 . H2061 . 0.980 no C206 . H2062 . 0.980 no C206 . H2063 . 0.980 no N17 . C17 . 1.388(11) yes N17 . C127 . 1.403(11) yes N17 . C137 . 1.452(11) yes O17 . C197 . 1.121(12) yes O27 . C197 . 1.353(12) yes O27 . C207 . 1.477(13) yes C17 . C27 . 1.375(12) yes C17 . C67 . 1.448(11) yes C27 . C37 . 1.370(12) yes C27 . H271 . 0.950 no C37 . C47 . 1.382(12) yes C37 . H371 . 0.950 no C47 . C57 . 1.364(12) yes C47 . H471 . 0.950 no C57 . C67 . 1.342(12) yes C57 . H571 . 0.950 no C67 . C77 . 1.445(11) yes C77 . C87 . 1.361(12) yes C77 . C127 . 1.406(11) yes C87 . C97 . 1.333(13) yes C87 . H871 . 0.950 no C97 . C107 . 1.434(13) yes C97 . H971 . 0.950 no C107 . C117 . 1.398(12) yes C107 . H1071 . 0.950 no C117 . C127 . 1.428(12) yes C117 . H1171 . 0.950 no C137 . C147 . 1.361(12) yes C137 . C187 . 1.410(12) yes C147 . C157 . 1.388(12) yes C147 . C197 . 1.500(12) yes C157 . C167 . 1.343(12) yes C157 . H1571 . 0.950 no C167 . C177 . 1.322(13) yes C167 . H1671 . 0.950 no C177 . C187 . 1.375(12) yes C177 . H1771 . 0.950 no C187 . H1871 . 0.950 no C207 . H2071 . 0.980 no C207 . H2072 . 0.980 no C207 . H2073 . 0.980 no N18 . C18 . 1.371(11) yes N18 . C128 . 1.368(11) yes N18 . C138 . 1.436(11) yes O18 . C198 . 1.233(12) yes O28 . C198 . 1.310(12) yes O28 . C208 . 1.394(13) yes C18 . C28 . 1.368(12) yes C18 . C68 . 1.357(11) yes C28 . C38 . 1.361(12) yes C28 . H281 . 0.950 no C38 . C48 . 1.393(12) yes C38 . H381 . 0.950 no C48 . C58 . 1.360(13) yes C48 . H481 . 0.950 no C58 . C68 . 1.433(12) yes C58 . H581 . 0.950 no C68 . C78 . 1.434(11) yes C78 . C88 . 1.428(12) yes C78 . C128 . 1.376(11) yes C88 . C98 . 1.404(13) yes C88 . H881 . 0.950 no C98 . C108 . 1.352(12) yes C98 . H981 . 0.950 no C108 . C118 . 1.359(12) yes C108 . H1081 . 0.950 no C118 . C128 . 1.336(12) yes C118 . H1181 . 0.950 no C138 . C148 . 1.387(12) yes C138 . C188 . 1.325(12) yes C148 . C158 . 1.405(12) yes C148 . C198 . 1.475(11) yes C158 . C168 . 1.399(12) yes C158 . H1581 . 0.950 no C168 . C178 . 1.417(13) yes C168 . H1681 . 0.950 no C178 . C188 . 1.388(12) yes C178 . H1781 . 0.950 no C188 . H1881 . 0.950 no C208 . H2081 . 0.980 no C208 . H2082 . 0.980 no C208 . H2083 . 0.980 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 C121 . N11 . C11 . 109.3(4) yes C121 . N11 . C131 . 123.8(5) yes C11 . N11 . C131 . 126.8(5) yes C191 . O21 . C201 . 118.6(7) yes N11 . C121 . C111 . 130.9(5) yes N11 . C121 . C71 . 105.2(4) yes C111 . C121 . C71 . 123.5(5) yes C121 . C111 . C101 . 117.3(6) yes C121 . C111 . H1111 . 121.1 no C101 . C111 . H1111 . 121.6 no C111 . C101 . C91 . 124.4(6) yes C111 . C101 . H1011 . 118.9 no C91 . C101 . H1011 . 116.7 no C101 . C91 . C81 . 122.1(6) yes C101 . C91 . H911 . 122.1 no C81 . C91 . H911 . 115.8 no C91 . C81 . C71 . 114.0(5) yes C91 . C81 . H811 . 123.5 no C71 . C81 . H811 . 122.5 no C81 . C71 . C121 . 118.6(5) yes C81 . C71 . C61 . 129.6(5) yes C121 . C71 . C61 . 111.5(5) yes C71 . C61 . C51 . 136.8(5) yes C71 . C61 . C11 . 104.3(4) yes C51 . C61 . C11 . 118.9(5) yes C61 . C51 . C41 . 120.1(6) yes C61 . C51 . H511 . 120.5 no C41 . C51 . H511 . 119.4 no C51 . C41 . C31 . 121.2(6) yes C51 . C41 . H411 . 122.6 no C31 . C41 . H411 . 116.2 no C41 . C31 . C21 . 121.2(5) yes C41 . C31 . H311 . 120.5 no C21 . C31 . H311 . 118.2 no C31 . C21 . C11 . 117.8(5) yes C31 . C21 . H211 . 120.9 no C11 . C21 . H211 . 121.3 no C61 . C11 . N11 . 109.6(4) yes C61 . C11 . C21 . 120.8(4) yes N11 . C11 . C21 . 129.6(5) yes N11 . C131 . C141 . 127.1(5) yes N11 . C131 . C181 . 116.2(5) yes C141 . C131 . C181 . 116.7(5) yes C131 . C141 . C151 . 119.8(5) yes C131 . C141 . C191 . 115.2(5) yes C151 . C141 . C191 . 124.3(6) yes C141 . C151 . C161 . 124.6(6) yes C141 . C151 . H1511 . 117.9 no C161 . C151 . H1511 . 117.5 no C151 . C161 . C171 . 118.0(6) yes C151 . C161 . H1611 . 121.2 no C171 . C161 . H1611 . 120.8 no C161 . C171 . C181 . 121.7(6) yes C161 . C171 . H1711 . 119.4 no C181 . C171 . H1711 . 118.9 no C131 . C181 . C171 . 119.3(5) yes C131 . C181 . H1811 . 120.0 no C171 . C181 . H1811 . 120.6 no C141 . C191 . O21 . 107.9(5) yes C141 . C191 . O11 . 134.3(6) yes O21 . C191 . O11 . 117.7(6) yes O21 . C201 . H2011 . 109.1 no O21 . C201 . H2012 . 108.3 no H2011 . C201 . H2012 . 109.5 no O21 . C201 . H2013 . 111.0 no H2011 . C201 . H2013 . 109.5 no H2012 . C201 . H2013 . 109.5 no C12 . N12 . C122 . 106.7(4) yes C12 . N12 . C132 . 128.8(5) yes C122 . N12 . C132 . 122.7(5) yes C192 . O22 . C202 . 117.3(7) yes N12 . C12 . C22 . 128.8(5) yes N12 . C12 . C62 . 109.4(4) yes C22 . C12 . C62 . 121.7(5) yes C12 . C22 . C32 . 117.8(5) yes C12 . C22 . H221 . 120.9 no C32 . C22 . H221 . 121.3 no C22 . C32 . C42 . 121.2(6) yes C22 . C32 . H321 . 119.2 no C42 . C32 . H321 . 119.5 no C32 . C42 . C52 . 121.3(6) yes C32 . C42 . H421 . 119.2 no C52 . C42 . H421 . 119.5 no C42 . C52 . C62 . 119.2(5) yes C42 . C52 . H521 . 120.3 no C62 . C52 . H521 . 120.6 no C12 . C62 . C52 . 118.9(5) yes C12 . C62 . C72 . 107.1(4) yes C52 . C62 . C72 . 134.0(5) yes C62 . C72 . C82 . 136.5(5) yes C62 . C72 . C122 . 110.3(4) yes C82 . C72 . C122 . 113.2(5) yes C72 . C82 . C92 . 118.3(5) yes C72 . C82 . H821 . 120.7 no C92 . C82 . H821 . 121.0 no C82 . C92 . C102 . 125.8(6) yes C82 . C92 . H921 . 117.0 no C102 . C92 . H921 . 117.3 no C92 . C102 . C112 . 117.1(6) yes C92 . C102 . H1021 . 121.3 no C112 . C102 . H1021 . 121.6 no C102 . C112 . C122 . 120.1(5) yes C102 . C112 . H1121 . 119.8 no C122 . C112 . H1121 . 120.1 no N12 . C122 . C72 . 106.1(4) yes N12 . C122 . C112 . 128.4(5) yes C72 . C122 . C112 . 125.5(5) yes N12 . C132 . C142 . 128.1(5) yes N12 . C132 . C182 . 116.7(5) yes C142 . C132 . C182 . 115.1(5) yes C132 . C142 . C152 . 122.6(5) yes C132 . C142 . C192 . 118.7(5) yes C152 . C142 . C192 . 118.7(5) yes C142 . C152 . C162 . 122.4(6) yes C142 . C152 . H1521 . 119.0 no C162 . C152 . H1521 . 118.7 no C152 . C162 . C172 . 120.5(6) yes C152 . C162 . H1621 . 119.9 no C172 . C162 . H1621 . 119.6 no C162 . C172 . C182 . 116.9(6) yes C162 . C172 . H1721 . 121.7 no C182 . C172 . H1721 . 121.3 no C132 . C182 . C172 . 122.6(5) yes C132 . C182 . H1821 . 118.5 no C172 . C182 . H1821 . 119.0 no C142 . C192 . O22 . 114.2(5) yes C142 . C192 . O12 . 122.1(5) yes O22 . C192 . O12 . 123.7(6) yes O22 . C202 . H2021 . 109.3 no O22 . C202 . H2022 . 110.4 no H2021 . C202 . H2022 . 109.5 no O22 . C202 . H2023 . 108.7 no H2021 . C202 . H2023 . 109.5 no H2022 . C202 . H2023 . 109.5 no C13 . N13 . C123 . 108.2(4) yes C13 . N13 . C133 . 124.1(5) yes C123 . N13 . C133 . 127.7(5) yes C193 . O23 . C203 . 118.6(7) yes N13 . C13 . C23 . 129.6(5) yes N13 . C13 . C63 . 109.2(4) yes C23 . C13 . C63 . 120.9(5) yes C13 . C23 . C33 . 117.7(5) yes C13 . C23 . H231 . 121.1 no C33 . C23 . H231 . 121.2 no C23 . C33 . C43 . 121.4(6) yes C23 . C33 . H331 . 119.3 no C43 . C33 . H331 . 119.3 no C33 . C43 . C53 . 121.2(6) yes C33 . C43 . H431 . 119.3 no C53 . C43 . H431 . 119.4 no C43 . C53 . C63 . 119.7(5) yes C43 . C53 . H531 . 120.1 no C63 . C53 . H531 . 120.2 no C13 . C63 . C53 . 119.1(5) yes C13 . C63 . C73 . 106.6(4) yes C53 . C63 . C73 . 134.2(5) yes C63 . C73 . C83 . 136.4(5) yes C63 . C73 . C123 . 106.4(4) yes C83 . C73 . C123 . 117.0(5) yes C73 . C83 . C93 . 119.5(5) yes C73 . C83 . H831 . 120.4 no C93 . C83 . H831 . 120.1 no C83 . C93 . C103 . 122.0(6) yes C83 . C93 . H931 . 119.2 no C103 . C93 . H931 . 118.8 no C93 . C103 . C113 . 122.0(6) yes C93 . C103 . H1031 . 119.2 no C113 . C103 . H1031 . 118.9 no C103 . C113 . C123 . 116.8(5) yes C103 . C113 . H1131 . 121.7 no C123 . C113 . H1131 . 121.4 no C73 . C123 . C113 . 122.7(5) yes C73 . C123 . N13 . 109.5(4) yes C113 . C123 . N13 . 127.7(5) yes N13 . C133 . C143 . 119.7(5) yes N13 . C133 . C183 . 118.7(5) yes C143 . C133 . C183 . 121.6(5) yes C133 . C143 . C153 . 116.7(5) yes C133 . C143 . C193 . 123.0(5) yes C153 . C143 . C193 . 120.3(5) yes C143 . C153 . C163 . 124.9(6) yes C143 . C153 . H1531 . 117.6 no C163 . C153 . H1531 . 117.5 no C153 . C163 . C173 . 117.2(6) yes C153 . C163 . H1631 . 121.4 no C173 . C163 . H1631 . 121.4 no C163 . C173 . C183 . 121.9(6) yes C163 . C173 . H1731 . 119.0 no C183 . C173 . H1731 . 119.0 no C133 . C183 . C173 . 117.6(5) yes C133 . C183 . H1831 . 121.2 no C173 . C183 . H1831 . 121.2 no C143 . C193 . O23 . 114.3(5) yes C143 . C193 . O13 . 128.4(6) yes O23 . C193 . O13 . 117.3(6) yes O23 . C203 . H2031 . 109.9 no O23 . C203 . H2032 . 110.3 no H2031 . C203 . H2032 . 109.5 no O23 . C203 . H2033 . 108.2 no H2031 . C203 . H2033 . 109.5 no H2032 . C203 . H2033 . 109.5 no C124 . N14 . C14 . 108.2(4) yes C124 . N14 . C134 . 126.1(5) yes C14 . N14 . C134 . 125.7(5) yes C194 . O24 . C204 . 115.1(7) yes N14 . C124 . C114 . 128.5(5) yes N14 . C124 . C74 . 110.5(4) yes C114 . C124 . C74 . 120.8(4) yes C124 . C114 . C104 . 116.6(5) yes C124 . C114 . H1141 . 121.8 no C104 . C114 . H1141 . 121.6 no C114 . C104 . C94 . 120.5(5) yes C114 . C104 . H1041 . 119.0 no C94 . C104 . H1041 . 120.5 no C104 . C94 . C84 . 118.3(5) yes C104 . C94 . H941 . 118.2 no C84 . C94 . H941 . 123.5 no C94 . C84 . C74 . 125.5(6) yes C94 . C84 . H841 . 117.0 no C74 . C84 . H841 . 117.6 no C124 . C74 . C84 . 118.3(5) yes C124 . C74 . C64 . 102.7(4) yes C84 . C74 . C64 . 138.9(5) yes C74 . C64 . C54 . 130.4(5) yes C74 . C64 . C14 . 111.1(5) yes C54 . C64 . C14 . 118.6(4) yes C64 . C54 . C44 . 117.8(5) yes C64 . C54 . H541 . 120.5 no C44 . C54 . H541 . 121.7 no C54 . C44 . C34 . 121.6(6) yes C54 . C44 . H441 . 116.5 no C34 . C44 . H441 . 122.0 no C44 . C34 . C24 . 121.0(6) yes C44 . C34 . H341 . 118.7 no C24 . C34 . H341 . 120.3 no C34 . C24 . C14 . 117.7(6) yes C34 . C24 . H241 . 121.2 no C14 . C24 . H241 . 121.1 no C24 . C14 . N14 . 129.0(5) yes C24 . C14 . C64 . 123.5(5) yes N14 . C14 . C64 . 107.5(4) yes N14 . C134 . C144 . 117.5(5) yes N14 . C134 . C184 . 119.8(5) yes C144 . C134 . C184 . 122.5(5) yes C134 . C144 . C154 . 118.7(5) yes C134 . C144 . C194 . 126.5(5) yes C154 . C144 . C194 . 114.6(5) yes C144 . C154 . C164 . 117.0(5) yes C144 . C154 . H1541 . 121.5 no C164 . C154 . H1541 . 121.5 no C154 . C164 . C174 . 122.5(6) yes C154 . C164 . H1641 . 118.8 no C174 . C164 . H1641 . 118.7 no C164 . C174 . C184 . 118.5(6) yes C164 . C174 . H1741 . 120.8 no C184 . C174 . H1741 . 120.7 no C174 . C184 . C134 . 120.8(6) yes C174 . C184 . H1841 . 119.6 no C134 . C184 . H1841 . 119.6 no C144 . C194 . O24 . 113.7(5) yes C144 . C194 . O14 . 119.8(6) yes O24 . C194 . O14 . 126.6(6) yes O24 . C204 . H2041 . 109.4 no O24 . C204 . H2042 . 108.8 no H2041 . C204 . H2042 . 109.5 no O24 . C204 . H2043 . 110.1 no H2041 . C204 . H2043 . 109.5 no H2042 . C204 . H2043 . 109.5 no C15 . N15 . C125 . 108.9(4) yes C15 . N15 . C135 . 128.0(5) yes C125 . N15 . C135 . 122.9(5) yes C195 . O25 . C205 . 114.5(7) yes N15 . C15 . C25 . 129.2(5) yes N15 . C15 . C65 . 107.5(4) yes C25 . C15 . C65 . 122.8(5) yes C15 . C25 . C35 . 117.8(5) yes C15 . C25 . H251 . 121.2 no C35 . C25 . H251 . 121.1 no C25 . C35 . C45 . 121.1(6) yes C25 . C35 . H351 . 119.5 no C45 . C35 . H351 . 119.4 no C35 . C45 . C55 . 121.2(6) yes C35 . C45 . H451 . 119.4 no C55 . C45 . H451 . 119.4 no C45 . C55 . C65 . 118.0(5) yes C45 . C55 . H551 . 121.1 no C65 . C55 . H551 . 121.0 no C55 . C65 . C15 . 119.0(5) yes C55 . C65 . C75 . 132.1(5) yes C15 . C65 . C75 . 108.5(4) yes C65 . C75 . C85 . 131.3(5) yes C65 . C75 . C125 . 107.3(4) yes C85 . C75 . C125 . 121.5(5) yes C75 . C85 . C95 . 119.9(5) yes C75 . C85 . H851 . 119.9 no C95 . C85 . H851 . 120.2 no C85 . C95 . C105 . 119.6(6) yes C85 . C95 . H951 . 119.9 no C105 . C95 . H951 . 120.4 no C95 . C105 . C115 . 119.5(6) yes C95 . C105 . H1051 . 120.1 no C115 . C105 . H1051 . 120.4 no C105 . C115 . C125 . 118.5(5) yes C105 . C115 . H1151 . 120.6 no C125 . C115 . H1151 . 120.9 no N15 . C125 . C115 . 131.3(5) yes N15 . C125 . C75 . 107.7(4) yes C115 . C125 . C75 . 121.0(5) yes N15 . C135 . C145 . 122.4(5) yes N15 . C135 . C185 . 119.3(5) yes C145 . C135 . C185 . 118.2(5) yes C135 . C145 . C155 . 120.8(5) yes C135 . C145 . C195 . 121.1(5) yes C155 . C145 . C195 . 118.1(5) yes C145 . C155 . C165 . 117.8(5) yes C145 . C155 . H1551 . 121.2 no C165 . C155 . H1551 . 121.0 no C155 . C165 . C175 . 122.3(6) yes C155 . C165 . H1651 . 119.0 no C175 . C165 . H1651 . 118.6 no C165 . C175 . C185 . 117.9(6) yes C165 . C175 . H1751 . 121.3 no C185 . C175 . H1751 . 120.8 no C175 . C185 . C135 . 123.1(6) yes C175 . C185 . H1851 . 118.7 no C135 . C185 . H1851 . 118.3 no C145 . C195 . O25 . 107.9(5) yes C145 . C195 . O15 . 120.4(5) yes O25 . C195 . O15 . 131.6(6) yes O25 . C205 . H2051 . 109.4 no O25 . C205 . H2052 . 110.7 no H2051 . C205 . H2052 . 109.5 no O25 . C205 . H2053 . 108.3 no H2051 . C205 . H2053 . 109.5 no H2052 . C205 . H2053 . 109.5 no C16 . N16 . C126 . 109.7(4) yes C16 . N16 . C136 . 123.8(5) yes C126 . N16 . C136 . 126.5(5) yes C196 . O26 . C206 . 114.6(7) yes N16 . C16 . C26 . 129.8(5) yes N16 . C16 . C66 . 108.6(4) yes C26 . C16 . C66 . 121.6(5) yes C16 . C26 . C36 . 117.5(5) yes C16 . C26 . H261 . 121.2 no C36 . C26 . H261 . 121.3 no C26 . C36 . C46 . 121.6(6) yes C26 . C36 . H361 . 119.2 no C46 . C36 . H361 . 119.2 no C36 . C46 . C56 . 121.4(6) yes C36 . C46 . H461 . 119.3 no C56 . C46 . H461 . 119.2 no C46 . C56 . C66 . 118.8(5) yes C46 . C56 . H561 . 120.6 no C66 . C56 . H561 . 120.6 no C56 . C66 . C16 . 119.1(5) yes C56 . C66 . C76 . 134.9(5) yes C16 . C66 . C76 . 106.0(4) yes C66 . C76 . C86 . 135.4(5) yes C66 . C76 . C126 . 103.2(4) yes C86 . C76 . C126 . 121.3(5) yes C76 . C86 . C96 . 121.4(5) yes C76 . C86 . H861 . 119.2 no C96 . C86 . H861 . 119.4 no C86 . C96 . C106 . 116.5(6) yes C86 . C96 . H961 . 121.8 no C106 . C96 . H961 . 121.8 no C96 . C106 . C116 . 125.3(6) yes C96 . C106 . H1061 . 117.4 no C116 . C106 . H1061 . 117.3 no C106 . C116 . C126 . 115.4(5) yes C106 . C116 . H1161 . 122.2 no C126 . C116 . H1161 . 122.3 no C76 . C126 . C116 . 120.1(5) yes C76 . C126 . N16 . 112.2(4) yes C116 . C126 . N16 . 127.6(5) yes N16 . C136 . C146 . 115.0(5) yes N16 . C136 . C186 . 119.8(5) yes C146 . C136 . C186 . 124.6(5) yes C136 . C146 . C156 . 112.5(5) yes C136 . C146 . C196 . 122.9(5) yes C156 . C146 . C196 . 124.4(5) yes C146 . C156 . C166 . 121.9(5) yes C146 . C156 . H1561 . 119.0 no C166 . C156 . H1561 . 119.1 no C156 . C166 . C176 . 118.8(6) yes C156 . C166 . H1661 . 120.6 no C176 . C166 . H1661 . 120.6 no C166 . C176 . C186 . 122.9(6) yes C166 . C176 . H1761 . 118.5 no C186 . C176 . H1761 . 118.6 no C136 . C186 . C176 . 119.2(6) yes C136 . C186 . H1861 . 120.4 no C176 . C186 . H1861 . 120.4 no C146 . C196 . O26 . 108.6(5) yes C146 . C196 . O16 . 130.5(6) yes O26 . C196 . O16 . 120.9(6) yes O26 . C206 . H2061 . 109.0 no O26 . C206 . H2062 . 110.2 no H2061 . C206 . H2062 . 109.5 no O26 . C206 . H2063 . 109.1 no H2061 . C206 . H2063 . 109.5 no H2062 . C206 . H2063 . 109.5 no C17 . N17 . C127 . 107.7(4) yes C17 . N17 . C137 . 122.8(5) yes C127 . N17 . C137 . 129.0(5) yes C197 . O27 . C207 . 111.9(7) yes N17 . C17 . C27 . 129.6(5) yes N17 . C17 . C67 . 109.6(4) yes C27 . C17 . C67 . 120.8(5) yes C17 . C27 . C37 . 117.7(5) yes C17 . C27 . H271 . 121.2 no C37 . C27 . H271 . 121.1 no C27 . C37 . C47 . 121.2(6) yes C27 . C37 . H371 . 119.4 no C47 . C37 . H371 . 119.4 no C37 . C47 . C57 . 121.4(6) yes C37 . C47 . H471 . 119.3 no C57 . C47 . H471 . 119.3 no C47 . C57 . C67 . 120.0(5) yes C47 . C57 . H571 . 120.0 no C67 . C57 . H571 . 120.1 no C17 . C67 . C57 . 118.9(5) yes C17 . C67 . C77 . 105.3(4) yes C57 . C67 . C77 . 135.8(5) yes C67 . C77 . C87 . 136.0(5) yes C67 . C77 . C127 . 107.7(4) yes C87 . C77 . C127 . 116.2(5) yes C77 . C87 . C97 . 122.9(5) yes C77 . C87 . H871 . 118.3 no C97 . C87 . H871 . 118.7 no C87 . C97 . C107 . 120.7(6) yes C87 . C97 . H971 . 119.4 no C107 . C97 . H971 . 119.9 no C97 . C107 . C117 . 121.1(6) yes C97 . C107 . H1071 . 119.1 no C117 . C107 . H1071 . 119.8 no C107 . C117 . C127 . 113.6(5) yes C107 . C117 . H1171 . 122.9 no C127 . C117 . H1171 . 123.5 no C117 . C127 . C77 . 125.5(5) yes C117 . C127 . N17 . 124.8(5) yes C77 . C127 . N17 . 109.6(4) yes N17 . C137 . C147 . 123.9(5) yes N17 . C137 . C187 . 114.6(5) yes C147 . C137 . C187 . 121.2(5) yes C137 . C147 . C157 . 117.0(5) yes C137 . C147 . C197 . 118.4(5) yes C157 . C147 . C197 . 124.5(5) yes C147 . C157 . C167 . 120.3(5) yes C147 . C157 . H1571 . 119.8 no C167 . C157 . H1571 . 119.9 no C157 . C167 . C177 . 124.3(6) yes C157 . C167 . H1671 . 117.8 no C177 . C167 . H1671 . 117.9 no C167 . C177 . C187 . 117.8(6) yes C167 . C177 . H1771 . 121.0 no C187 . C177 . H1771 . 121.2 no C137 . C187 . C177 . 119.4(5) yes C137 . C187 . H1871 . 120.4 no C177 . C187 . H1871 . 120.1 no C147 . C197 . O27 . 106.5(5) yes C147 . C197 . O17 . 126.9(5) yes O27 . C197 . O17 . 126.6(6) yes O27 . C207 . H2071 . 109.1 no O27 . C207 . H2072 . 108.2 no H2071 . C207 . H2072 . 109.5 no O27 . C207 . H2073 . 111.1 no H2071 . C207 . H2073 . 109.5 no H2072 . C207 . H2073 . 109.5 no C18 . N18 . C128 . 109.8(4) yes C18 . N18 . C138 . 126.2(5) yes C128 . N18 . C138 . 123.6(5) yes C198 . O28 . C208 . 119.9(7) yes N18 . C18 . C28 . 129.2(5) yes N18 . C18 . C68 . 107.4(4) yes C28 . C18 . C68 . 123.4(5) yes C18 . C28 . C38 . 117.7(5) yes C18 . C28 . H281 . 121.1 no C38 . C28 . H281 . 121.2 no C28 . C38 . C48 . 121.1(6) yes C28 . C38 . H381 . 119.3 no C48 . C38 . H381 . 119.5 no C38 . C48 . C58 . 121.4(6) yes C38 . C48 . H481 . 119.2 no C58 . C48 . H481 . 119.4 no C48 . C58 . C68 . 117.5(5) yes C48 . C58 . H581 . 121.2 no C68 . C58 . H581 . 121.4 no C58 . C68 . C18 . 118.9(5) yes C58 . C68 . C78 . 132.7(5) yes C18 . C68 . C78 . 108.4(4) yes C68 . C78 . C88 . 133.6(5) yes C68 . C78 . C128 . 105.9(4) yes C88 . C78 . C128 . 120.5(5) yes C78 . C88 . C98 . 115.8(5) yes C78 . C88 . H881 . 122.2 no C98 . C88 . H881 . 122.1 no C88 . C98 . C108 . 120.9(6) yes C88 . C98 . H981 . 119.6 no C108 . C98 . H981 . 119.5 no C98 . C108 . C118 . 122.0(6) yes C98 . C108 . H1081 . 119.0 no C118 . C108 . H1081 . 119.0 no C108 . C118 . C128 . 119.7(5) yes C108 . C118 . H1181 . 120.2 no C128 . C118 . H1181 . 120.1 no C78 . C128 . N18 . 108.2(4) yes C78 . C128 . C118 . 121.2(5) yes N18 . C128 . C118 . 130.5(5) yes N18 . C138 . C148 . 119.1(5) yes N18 . C138 . C188 . 119.4(5) yes C148 . C138 . C188 . 121.2(5) yes C138 . C148 . C158 . 119.1(5) yes C138 . C148 . C198 . 124.7(5) yes C158 . C148 . C198 . 116.2(5) yes C148 . C158 . C168 . 121.2(5) yes C148 . C158 . H1581 . 119.2 no C168 . C158 . H1581 . 119.5 no C158 . C168 . C178 . 116.3(6) yes C158 . C168 . H1681 . 121.7 no C178 . C168 . H1681 . 122.0 no C168 . C178 . C188 . 121.4(6) yes C168 . C178 . H1781 . 119.2 no C188 . C178 . H1781 . 119.4 no C178 . C188 . C138 . 120.8(5) yes C178 . C188 . H1881 . 119.5 no C138 . C188 . H1881 . 119.7 no C148 . C198 . O28 . 117.2(6) yes C148 . C198 . O18 . 124.7(6) yes O28 . C198 . O18 . 117.7(6) yes O28 . C208 . H2081 . 109.5 no O28 . C208 . H2082 . 109.0 no H2081 . C208 . H2082 . 109.5 no O28 . C208 . H2083 . 109.9 no H2081 . C208 . H2083 . 109.5 no H2082 . C208 . H2083 . 109.5 no _chemical_name_common 'Methyl 2-(9H-carbazol-9-yl)benzoate' _exptl_crystal_recrystallization_method ; A mixture of carbazole, methyl 2-iodobenzoate, copper powder, potassium carbonate and nitrobenzene were heated at 175 degrees C for 48 h. After cooling, the resultant mixture was a red solid. A mixture of water/chloroform (1:1) was added to the solid, and the two layers separated. The aqueous layer was then extracted twice with chloroform, and the organic layers were combined and dried over MgSO4. The solvent was removed under reduced pressure, and the residue oil was purified by flash dry chromatography on silica using hexane/ethyl acetate (85:15) as the eluant. This resulted in the formation of colourless crystals. (5.30 g, 88%) ; #edit data_3_7GPa_I.cif _database_code_depnum_ccdc_archive 'CCDC 752558' #_oxford_structure_analysis_title 'mben07 in Pn' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 7.1346(6) _cell_length_b 14.165(2) _cell_length_c 50.433(8) _cell_angle_alpha 90 _cell_angle_beta 89.880(9) _cell_angle_gamma 90 _cell_volume 5096.7(11) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 n 1 ' _symmetry_space_group_name_Hall 'P -2yac' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y,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 0.0000 0.0010 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0010 0.0010 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0030 0.0030 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 16 # Given Formula = C15 H11.25 N0.75 O1.50 # Dc = 1.18 Fooo = 2528.00 Mu = 0.76 M = 1808.07 # Found Formula = C20 H15 N1 O2 # Dc = 1.57 FOOO = 2528.00 Mu = 1.02 M = 2410.76 _chemical_formula_sum 'C20 H15 N1 O2' _chemical_formula_moiety 'C20 H15 N1 O2' _chemical_compound_source ? _chemical_formula_weight 301.34 _cell_measurement_reflns_used 983 _cell_measurement_theta_min 2 _cell_measurement_theta_max 13 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.571 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 2528 _exptl_absorpt_coefficient_mu 0.102 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.86 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device APEX-II _diffrn_measurement_device_type Area _diffrn_radiation_monochromator silicon _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.47620 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 293 _diffrn_ambient_pressure 3700000 _diffrn_reflns_number 15739 _reflns_number_total 3890 _diffrn_reflns_av_R_equivalents 0.1512 # Number of reflections with Friedels Law is 3890 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5196 _diffrn_reflns_reduction_process ; Merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 ; _diffrn_reflns_theta_min 1.105 _diffrn_reflns_theta_max 13.642 _diffrn_measured_fraction_theta_max 0.753 _diffrn_reflns_theta_full 10.232 _diffrn_measured_fraction_theta_full 0.804 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 44 _reflns_limit_h_min -7 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 44 #_oxford_diffrn_Wilson_B_factor 0.63 #_oxford_diffrn_Wilson_scale 0.75 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.38 _refine_diff_density_max 0.36 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement #_oxford_reflns_threshold_expression_ref I>2.0\s(I) _refine_ls_number_reflns 2773 _refine_ls_number_restraints 1154 _refine_ls_number_parameters 738 #_oxford_refine_ls_R_factor_ref 0.0839 _refine_ls_wR_factor_ref 0.0890 _refine_ls_goodness_of_fit_ref 1.0078 _refine_ls_shift/su_max 0.006125 # The values computed from all data #_oxford_reflns_number_all 3858 _refine_ls_R_factor_all 0.1203 _refine_ls_wR_factor_all 0.1336 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2773 _refine_ls_R_factor_gt 0.0839 _refine_ls_wR_factor_gt 0.0890 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 13.6 -10.2 8.48 ; 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens N11 N -0.071(2) 0.6820(9) -0.1387(3) 0.028(2) 1.0000 Uiso D U . . . . . O11 O 0.099(2) 0.6634(16) -0.0857(4) 0.027(3) 1.0000 Uiso D U . . . . . O21 O -0.110(2) 0.7227(16) -0.0601(4) 0.026(3) 1.0000 Uiso D U . . . . . C121 C 0.0179(17) 0.7753(9) -0.1349(3) 0.028(3) 1.0000 Uiso D U . . . . . C111 C -0.028(2) 0.8445(12) -0.1199(3) 0.028(3) 1.0000 Uiso D U . . . . . C101 C 0.062(2) 0.9238(11) -0.1232(3) 0.028(3) 1.0000 Uiso D U . . . . . C91 C 0.201(2) 0.9374(11) -0.1414(3) 0.028(3) 1.0000 Uiso D U . . . . . C81 C 0.259(2) 0.8688(12) -0.1575(3) 0.029(3) 1.0000 Uiso D U . . . . . C71 C 0.1585(18) 0.7802(9) -0.1541(3) 0.028(3) 1.0000 Uiso D U . . . . . C61 C 0.1734(18) 0.6916(10) -0.1693(3) 0.028(3) 1.0000 Uiso D U . . . . . C51 C 0.277(2) 0.6591(12) -0.1894(3) 0.029(3) 1.0000 Uiso D U . . . . . C41 C 0.241(2) 0.5724(13) -0.2000(3) 0.029(3) 1.0000 Uiso D U . . . . . C31 C 0.098(2) 0.5164(11) -0.1904(3) 0.029(3) 1.0000 Uiso D U . . . . . C21 C -0.014(2) 0.5459(11) -0.1698(3) 0.029(3) 1.0000 Uiso D U . . . . . C11 C 0.0226(18) 0.6337(9) -0.1591(3) 0.028(3) 1.0000 Uiso D U . . . . . C131 C -0.2164(17) 0.6493(9) -0.1238(3) 0.027(3) 1.0000 Uiso D U . . . . . C141 C -0.2286(18) 0.6471(9) -0.0961(3) 0.026(3) 1.0000 Uiso D U . . . . . C151 C -0.386(2) 0.6116(10) -0.0841(3) 0.026(3) 1.0000 Uiso D U . . . . . C161 C -0.535(2) 0.5786(10) -0.0970(4) 0.026(3) 1.0000 Uiso D U . . . . . C171 C -0.531(2) 0.5806(10) -0.1245(4) 0.026(3) 1.0000 Uiso D U . . . . . C181 C -0.378(2) 0.6147(10) -0.1383(3) 0.027(3) 1.0000 Uiso D U . . . . . C191 C -0.0585(17) 0.6748(18) -0.0821(4) 0.026(3) 1.0000 Uiso D U . . . . . C201 C 0.036(3) 0.756(2) -0.0422(5) 0.028(4) 1.0000 Uiso D U . . . . . N12 N 0.090(2) 0.2995(9) 0.0027(3) 0.025(2) 1.0000 Uiso D U . . . . . O12 O -0.112(2) 0.2362(16) -0.0390(4) 0.029(3) 1.0000 Uiso D U . . . . . O22 O 0.058(2) 0.1842(17) -0.0725(3) 0.027(3) 1.0000 Uiso D U . . . . . C12 C 0.0142(17) 0.3835(9) -0.0059(3) 0.026(3) 1.0000 Uiso D U . . . . . C22 C 0.077(2) 0.4424(11) -0.0257(3) 0.026(3) 1.0000 Uiso D U . . . . . C32 C -0.020(2) 0.5240(11) -0.0302(3) 0.026(3) 1.0000 Uiso D U . . . . . C42 C -0.177(2) 0.5467(11) -0.0153(3) 0.026(3) 1.0000 Uiso D U . . . . . C52 C -0.241(2) 0.4877(11) 0.0045(3) 0.026(3) 1.0000 Uiso D U . . . . . C62 C -0.1469(18) 0.4055(9) 0.0095(3) 0.026(3) 1.0000 Uiso D U . . . . . C72 C -0.1676(17) 0.3357(10) 0.0274(3) 0.025(3) 1.0000 Uiso D U . . . . . C82 C -0.299(2) 0.3129(12) 0.0487(3) 0.025(3) 1.0000 Uiso D U . . . . . C92 C -0.278(2) 0.2269(13) 0.0617(3) 0.026(3) 1.0000 Uiso D U . . . . . C102 C -0.148(2) 0.1621(11) 0.0566(3) 0.026(3) 1.0000 Uiso D U . . . . . C112 C -0.020(2) 0.1823(11) 0.0365(3) 0.026(3) 1.0000 Uiso D U . . . . . C122 C -0.0321(17) 0.2645(9) 0.0231(3) 0.025(3) 1.0000 Uiso D U . . . . . C132 C 0.2256(17) 0.2454(9) -0.0088(3) 0.026(2) 1.0000 Uiso D U . . . . . C142 C 0.2196(17) 0.2008(10) -0.0323(3) 0.026(3) 1.0000 Uiso D U . . . . . C152 C 0.370(2) 0.1530(10) -0.0426(3) 0.026(3) 1.0000 Uiso D U . . . . . C162 C 0.531(2) 0.1477(10) -0.0301(4) 0.026(3) 1.0000 Uiso D U . . . . . C172 C 0.555(2) 0.1918(11) -0.0059(4) 0.026(3) 1.0000 Uiso D U . . . . . C182 C 0.399(2) 0.2402(10) 0.0046(3) 0.026(3) 1.0000 Uiso D U . . . . . C192 C 0.039(2) 0.208(2) -0.0487(3) 0.027(3) 1.0000 Uiso D U . . . . . C202 C -0.110(3) 0.184(3) -0.0891(5) 0.029(4) 1.0000 Uiso D U . . . . . N13 N 0.559(2) 0.3706(9) 0.1168(3) 0.027(2) 1.0000 Uiso D U . . . . . O13 O 0.380(2) 0.4129(16) 0.1681(4) 0.030(3) 1.0000 Uiso D U . . . . . O23 O 0.587(2) 0.3544(16) 0.1959(3) 0.029(3) 1.0000 Uiso D U . . . . . C13 C 0.4837(17) 0.2824(9) 0.1229(3) 0.027(3) 1.0000 Uiso D U . . . . . C23 C 0.543(2) 0.2163(11) 0.1408(3) 0.027(3) 1.0000 Uiso D U . . . . . C33 C 0.454(2) 0.1304(11) 0.1409(3) 0.027(3) 1.0000 Uiso D U . . . . . C43 C 0.309(2) 0.1112(11) 0.1237(3) 0.027(3) 1.0000 Uiso D U . . . . . C53 C 0.249(2) 0.1768(11) 0.1060(3) 0.027(3) 1.0000 Uiso D U . . . . . C63 C 0.3321(18) 0.2626(9) 0.1051(3) 0.027(3) 1.0000 Uiso D U . . . . . C73 C 0.3088(18) 0.3436(9) 0.0893(3) 0.027(3) 1.0000 Uiso D U . . . . . C83 C 0.198(2) 0.3694(12) 0.0682(3) 0.027(3) 1.0000 Uiso D U . . . . . C93 C 0.234(2) 0.4549(13) 0.0549(3) 0.028(3) 1.0000 Uiso D U . . . . . C103 C 0.373(2) 0.5131(11) 0.0622(3) 0.028(3) 1.0000 Uiso D U . . . . . C113 C 0.492(2) 0.4919(11) 0.0832(3) 0.027(3) 1.0000 Uiso D U . . . . . C123 C 0.4584(18) 0.4083(9) 0.0966(3) 0.027(3) 1.0000 Uiso D U . . . . . C133 C 0.7127(17) 0.4115(9) 0.1303(3) 0.027(3) 1.0000 Uiso D U . . . . . C143 C 0.7053(17) 0.4219(10) 0.1572(3) 0.028(3) 1.0000 Uiso D U . . . . . C153 C 0.863(2) 0.4649(10) 0.1695(3) 0.027(3) 1.0000 Uiso D U . . . . . C163 C 1.013(2) 0.4940(10) 0.1571(4) 0.028(3) 1.0000 Uiso D U . . . . . C173 C 1.017(2) 0.4822(10) 0.1284(4) 0.027(3) 1.0000 Uiso D U . . . . . C183 C 0.873(2) 0.4421(10) 0.1150(3) 0.027(3) 1.0000 Uiso D U . . . . . C193 C 0.5456(17) 0.3964(17) 0.1726(3) 0.029(3) 1.0000 Uiso D U . . . . . C203 C 0.434(3) 0.324(2) 0.2126(5) 0.031(4) 1.0000 Uiso D U . . . . . N14 N -0.067(2) 0.2024(9) 0.2569(4) 0.029(3) 1.0000 Uiso D U . . . . . O14 O 0.114(2) 0.1675(17) 0.2077(4) 0.034(3) 1.0000 Uiso D U . . . . . O24 O -0.091(2) 0.2198(16) 0.1761(4) 0.033(3) 1.0000 Uiso D U . . . . . C124 C 0.0138(18) 0.2874(9) 0.2532(3) 0.029(3) 1.0000 Uiso D U . . . . . C114 C -0.044(2) 0.3638(12) 0.2352(3) 0.029(3) 1.0000 Uiso D U . . . . . C104 C 0.055(2) 0.4514(12) 0.2374(3) 0.030(3) 1.0000 Uiso D U . . . . . C94 C 0.200(2) 0.4618(11) 0.2560(4) 0.030(3) 1.0000 Uiso D U . . . . . C84 C 0.246(2) 0.3838(12) 0.2720(3) 0.030(3) 1.0000 Uiso D U . . . . . C74 C 0.1618(18) 0.3009(9) 0.2715(3) 0.029(3) 1.0000 Uiso D U . . . . . C64 C 0.1621(18) 0.2158(10) 0.2858(3) 0.029(3) 1.0000 Uiso D U . . . . . C54 C 0.280(2) 0.1851(12) 0.3075(3) 0.029(3) 1.0000 Uiso D U . . . . . C44 C 0.251(2) 0.0969(14) 0.3176(3) 0.029(3) 1.0000 Uiso D U . . . . . C34 C 0.113(2) 0.0379(11) 0.3075(3) 0.029(3) 1.0000 Uiso D U . . . . . C24 C -0.001(2) 0.0671(11) 0.2869(3) 0.029(3) 1.0000 Uiso D U . . . . . C14 C 0.0286(18) 0.1560(9) 0.2767(3) 0.029(3) 1.0000 Uiso D U . . . . . C134 C -0.2318(17) 0.1655(9) 0.2422(3) 0.029(3) 1.0000 Uiso D U . . . . . C144 C -0.2117(17) 0.1521(10) 0.2158(3) 0.030(3) 1.0000 Uiso D U . . . . . C154 C -0.362(2) 0.1134(10) 0.2015(3) 0.030(3) 1.0000 Uiso D U . . . . . C164 C -0.524(2) 0.0882(10) 0.2160(4) 0.030(3) 1.0000 Uiso D U . . . . . C174 C -0.538(2) 0.1015(10) 0.2424(4) 0.030(3) 1.0000 Uiso D U . . . . . C184 C -0.387(2) 0.1399(10) 0.2555(3) 0.030(3) 1.0000 Uiso D U . . . . . C194 C -0.0449(17) 0.1802(19) 0.1991(3) 0.032(3) 1.0000 Uiso D U . . . . . C204 C 0.061(3) 0.255(3) 0.1612(5) 0.034(4) 1.0000 Uiso D U . . . . . N15 N 0.041(2) 0.1151(9) 0.5009(3) 0.023(2) 1.0000 Uiso D U . . . . . O15 O -0.128(2) 0.0920(16) 0.4500(4) 0.025(3) 1.0000 Uiso D U . . . . . O25 O 0.083(2) 0.1520(15) 0.4213(4) 0.026(3) 1.0000 Uiso D U . . . . . C15 C -0.0489(17) 0.2014(9) 0.4973(3) 0.023(3) 1.0000 Uiso D U . . . . . C25 C 0.0012(19) 0.2764(11) 0.4812(3) 0.023(3) 1.0000 Uiso D U . . . . . C35 C -0.091(2) 0.3607(11) 0.4849(3) 0.023(3) 1.0000 Uiso D U . . . . . C45 C -0.230(2) 0.3702(11) 0.5039(3) 0.024(3) 1.0000 Uiso D U . . . . . C55 C -0.2819(19) 0.2962(12) 0.5195(3) 0.023(3) 1.0000 Uiso D U . . . . . C65 C -0.1860(17) 0.2076(9) 0.5159(3) 0.023(3) 1.0000 Uiso D U . . . . . C75 C -0.1930(18) 0.1189(9) 0.5306(3) 0.023(3) 1.0000 Uiso D U . . . . . C85 C -0.308(2) 0.0899(12) 0.5514(3) 0.024(3) 1.0000 Uiso D U . . . . . C95 C -0.282(2) 0.0096(13) 0.5623(3) 0.024(3) 1.0000 Uiso D U . . . . . C105 C -0.132(2) -0.0518(11) 0.5527(3) 0.024(3) 1.0000 Uiso D U . . . . . C115 C -0.019(2) -0.0218(11) 0.5323(3) 0.024(3) 1.0000 Uiso D U . . . . . C125 C -0.0531(18) 0.0641(9) 0.5215(3) 0.023(3) 1.0000 Uiso D U . . . . . C135 C 0.1948(17) 0.0777(9) 0.4864(3) 0.023(3) 1.0000 Uiso D U . . . . . C145 C 0.1993(17) 0.0762(9) 0.4583(3) 0.023(3) 1.0000 Uiso D U . . . . . C155 C 0.349(2) 0.0431(10) 0.4453(3) 0.023(3) 1.0000 Uiso D U . . . . . C165 C 0.502(2) 0.0097(10) 0.4608(4) 0.023(3) 1.0000 Uiso D U . . . . . C175 C 0.500(2) 0.0107(10) 0.4865(4) 0.023(3) 1.0000 Uiso D U . . . . . C185 C 0.340(2) 0.0462(10) 0.4991(3) 0.023(3) 1.0000 Uiso D U . . . . . C195 C 0.0249(17) 0.1067(18) 0.4419(4) 0.025(3) 1.0000 Uiso D U . . . . . C205 C -0.064(3) 0.190(2) 0.4047(5) 0.027(4) 1.0000 Uiso D U . . . . . N16 N 0.545(2) 0.2249(9) 0.6041(3) 0.027(2) 1.0000 Uiso D U . . . . . O16 O 0.372(2) 0.2667(16) 0.6501(4) 0.029(3) 1.0000 Uiso D U . . . . . O26 O 0.546(2) 0.3082(16) 0.6846(3) 0.028(3) 1.0000 Uiso D U . . . . . C16 C 0.4642(17) 0.1369(9) 0.6096(3) 0.027(3) 1.0000 Uiso D U . . . . . C26 C 0.513(2) 0.0704(11) 0.6282(3) 0.027(3) 1.0000 Uiso D U . . . . . C36 C 0.416(2) -0.0139(11) 0.6281(3) 0.028(3) 1.0000 Uiso D U . . . . . C46 C 0.275(2) -0.0311(11) 0.6101(4) 0.028(3) 1.0000 Uiso D U . . . . . C56 C 0.225(2) 0.0339(12) 0.5920(3) 0.028(3) 1.0000 Uiso D U . . . . . C66 C 0.3201(18) 0.1210(9) 0.5915(3) 0.027(3) 1.0000 Uiso D U . . . . . C76 C 0.3119(18) 0.2087(10) 0.5741(3) 0.027(3) 1.0000 Uiso D U . . . . . C86 C 0.199(2) 0.2391(12) 0.5543(3) 0.028(3) 1.0000 Uiso D U . . . . . C96 C 0.213(2) 0.3261(14) 0.5445(3) 0.028(3) 1.0000 Uiso D U . . . . . C106 C 0.350(2) 0.3854(11) 0.5562(3) 0.029(3) 1.0000 Uiso D U . . . . . C116 C 0.470(2) 0.3591(11) 0.5761(3) 0.028(3) 1.0000 Uiso D U . . . . . C126 C 0.4482(18) 0.2679(9) 0.5853(3) 0.027(3) 1.0000 Uiso D U . . . . . C136 C 0.7164(17) 0.2596(9) 0.6171(3) 0.027(3) 1.0000 Uiso D U . . . . . C146 C 0.6893(17) 0.2942(10) 0.6441(3) 0.027(3) 1.0000 Uiso D U . . . . . C156 C 0.848(2) 0.3410(10) 0.6539(3) 0.027(3) 1.0000 Uiso D U . . . . . C166 C 1.012(2) 0.3533(10) 0.6384(4) 0.027(3) 1.0000 Uiso D U . . . . . C176 C 1.016(2) 0.3165(11) 0.6134(4) 0.027(3) 1.0000 Uiso D U . . . . . C186 C 0.872(2) 0.2711(10) 0.6028(3) 0.027(3) 1.0000 Uiso D U . . . . . C196 C 0.5159(19) 0.287(2) 0.6576(3) 0.027(3) 1.0000 Uiso D U . . . . . C206 C 0.381(3) 0.303(3) 0.7011(4) 0.029(4) 1.0000 Uiso D U . . . . . N17 N -0.119(2) 0.2003(9) 0.7474(3) 0.026(2) 1.0000 Uiso D U . . . . . O17 O 0.055(2) 0.1518(16) 0.7020(4) 0.030(3) 1.0000 Uiso D U . . . . . O27 O -0.122(2) 0.1014(16) 0.6688(3) 0.030(3) 1.0000 Uiso D U . . . . . C17 C -0.0088(18) 0.1637(9) 0.7675(3) 0.026(3) 1.0000 Uiso D U . . . . . C27 C -0.028(2) 0.0812(11) 0.7815(3) 0.026(3) 1.0000 Uiso D U . . . . . C37 C 0.095(2) 0.0648(11) 0.8017(3) 0.026(3) 1.0000 Uiso D U . . . . . C47 C 0.233(2) 0.1294(13) 0.8080(3) 0.026(3) 1.0000 Uiso D U . . . . . C57 C 0.253(2) 0.2112(12) 0.7942(3) 0.026(3) 1.0000 Uiso D U . . . . . C67 C 0.1361(18) 0.2310(9) 0.7743(3) 0.025(3) 1.0000 Uiso D U . . . . . C77 C 0.1060(18) 0.3104(9) 0.7569(3) 0.025(3) 1.0000 Uiso D U . . . . . C87 C 0.185(2) 0.3966(11) 0.7534(3) 0.026(3) 1.0000 Uiso D U . . . . . C97 C 0.125(2) 0.4582(11) 0.7354(4) 0.026(3) 1.0000 Uiso D U . . . . . C107 C -0.028(2) 0.4357(11) 0.7182(3) 0.026(3) 1.0000 Uiso D U . . . . . C117 C -0.120(2) 0.3488(11) 0.7201(3) 0.026(3) 1.0000 Uiso D U . . . . . C127 C -0.0450(18) 0.2884(9) 0.7402(3) 0.026(3) 1.0000 Uiso D U . . . . . C137 C -0.2675(17) 0.1471(9) 0.7349(3) 0.026(3) 1.0000 Uiso D U . . . . . C147 C -0.2624(17) 0.1166(10) 0.7093(3) 0.026(3) 1.0000 Uiso D U . . . . . C157 C -0.424(2) 0.0748(10) 0.6995(3) 0.026(3) 1.0000 Uiso D U . . . . . C167 C -0.577(2) 0.0664(10) 0.7149(4) 0.026(3) 1.0000 Uiso D U . . . . . C177 C -0.587(2) 0.0952(11) 0.7398(4) 0.025(3) 1.0000 Uiso D U . . . . . C187 C -0.430(2) 0.1365(10) 0.7506(3) 0.025(3) 1.0000 Uiso D U . . . . . C197 C -0.084(2) 0.129(2) 0.6939(3) 0.029(3) 1.0000 Uiso D U . . . . . C207 C 0.041(3) 0.113(3) 0.6512(4) 0.031(4) 1.0000 Uiso D U . . . . . N18 N 0.3737(19) 0.2714(9) 0.8605(3) 0.023(2) 1.0000 Uiso D U . . . . . O18 O 0.570(2) 0.3331(16) 0.9036(4) 0.028(3) 1.0000 Uiso D U . . . . . O28 O 0.409(2) 0.3898(17) 0.9369(3) 0.026(3) 1.0000 Uiso D U . . . . . C18 C 0.4910(17) 0.3086(9) 0.8416(3) 0.023(3) 1.0000 Uiso D U . . . . . C28 C 0.476(2) 0.3920(11) 0.8278(3) 0.024(3) 1.0000 Uiso D U . . . . . C38 C 0.603(2) 0.4084(11) 0.8079(3) 0.025(3) 1.0000 Uiso D U . . . . . C48 C 0.741(2) 0.3425(13) 0.8017(3) 0.025(3) 1.0000 Uiso D U . . . . . C58 C 0.7566(19) 0.2599(12) 0.8154(3) 0.024(3) 1.0000 Uiso D U . . . . . C68 C 0.6241(17) 0.2428(9) 0.8363(3) 0.023(3) 1.0000 Uiso D U . . . . . C78 C 0.6024(17) 0.1669(9) 0.8549(3) 0.023(3) 1.0000 Uiso D U . . . . . C88 C 0.702(2) 0.0816(11) 0.8594(3) 0.023(3) 1.0000 Uiso D U . . . . . C98 C 0.630(2) 0.0235(10) 0.8796(3) 0.023(3) 1.0000 Uiso D U . . . . . C108 C 0.476(2) 0.0491(11) 0.8935(3) 0.024(3) 1.0000 Uiso D U . . . . . C118 C 0.3846(19) 0.1307(11) 0.8886(3) 0.024(3) 1.0000 Uiso D U . . . . . C128 C 0.4460(17) 0.1884(9) 0.8697(3) 0.023(3) 1.0000 Uiso D U . . . . . C138 C 0.2178(17) 0.3186(9) 0.8727(3) 0.024(2) 1.0000 Uiso D U . . . . . C148 C 0.2445(17) 0.3659(10) 0.8966(3) 0.025(3) 1.0000 Uiso D U . . . . . C158 C 0.097(2) 0.4201(10) 0.9072(3) 0.025(3) 1.0000 Uiso D U . . . . . C168 C -0.076(2) 0.4273(10) 0.8940(4) 0.025(3) 1.0000 Uiso D U . . . . . C178 C -0.091(2) 0.3766(11) 0.8698(4) 0.025(3) 1.0000 Uiso D U . . . . . C188 C 0.057(2) 0.3238(10) 0.8598(3) 0.024(3) 1.0000 Uiso D U . . . . . C198 C 0.4201(19) 0.365(2) 0.9118(3) 0.026(3) 1.0000 Uiso D U . . . . . C208 C 0.570(3) 0.392(3) 0.9525(5) 0.026(4) 1.0000 Uiso D U . . . . . H1111 H -0.1227 0.8381 -0.1068 0.0321 1.0000 Uiso R . . . . . . H1011 H 0.0292 0.9767 -0.1126 0.0319 1.0000 Uiso R . . . . . . H911 H 0.2639 0.9962 -0.1433 0.0323 1.0000 Uiso R . . . . . . H811 H 0.3555 0.8765 -0.1703 0.0327 1.0000 Uiso R . . . . . . H511 H 0.3756 0.6962 -0.1966 0.0336 1.0000 Uiso R . . . . . . H411 H 0.3111 0.5472 -0.2144 0.0336 1.0000 Uiso R . . . . . . H311 H 0.0743 0.4559 -0.1978 0.0330 1.0000 Uiso R . . . . . . H211 H -0.1119 0.5072 -0.1632 0.0330 1.0000 Uiso R . . . . . . H1511 H -0.3891 0.6105 -0.0653 0.0324 1.0000 Uiso R . . . . . . H1611 H -0.6397 0.5540 -0.0877 0.0326 1.0000 Uiso R . . . . . . H1711 H -0.6361 0.5580 -0.1342 0.0333 1.0000 Uiso R . . . . . . H1811 H -0.3778 0.6156 -0.1572 0.0335 1.0000 Uiso R . . . . . . H2011 H -0.0221 0.7881 -0.0271 0.0324 1.0000 Uiso R . . . . . . H2012 H 0.1155 0.8007 -0.0519 0.0324 1.0000 Uiso R . . . . . . H2013 H 0.1123 0.7032 -0.0359 0.0324 1.0000 Uiso R . . . . . . H221 H 0.1840 0.4269 -0.0361 0.0344 1.0000 Uiso R . . . . . . H321 H 0.0196 0.5657 -0.0438 0.0348 1.0000 Uiso R . . . . . . H421 H -0.2410 0.6041 -0.0187 0.0349 1.0000 Uiso R . . . . . . H521 H -0.3492 0.5040 0.0145 0.0343 1.0000 Uiso R . . . . . . H821 H -0.3952 0.3557 0.0535 0.0331 1.0000 Uiso R . . . . . . H921 H -0.3644 0.2137 0.0756 0.0332 1.0000 Uiso R . . . . . . H1021 H -0.1436 0.1045 0.0662 0.0332 1.0000 Uiso R . . . . . . H1121 H 0.0753 0.1380 0.0323 0.0329 1.0000 Uiso R . . . . . . H1521 H 0.3573 0.1232 -0.0594 0.0320 1.0000 Uiso R . . . . . . H1621 H 0.6321 0.1134 -0.0378 0.0320 1.0000 Uiso R . . . . . . H1721 H 0.6706 0.1890 0.0034 0.0322 1.0000 Uiso R . . . . . . H1821 H 0.4114 0.2706 0.0213 0.0327 1.0000 Uiso R . . . . . . H2021 H -0.0774 0.1641 -0.1071 0.0328 1.0000 Uiso R . . . . . . H2022 H -0.1596 0.2489 -0.0896 0.0328 1.0000 Uiso R . . . . . . H2023 H -0.2054 0.1418 -0.0818 0.0328 1.0000 Uiso R . . . . . . H231 H 0.6425 0.2294 0.1528 0.0363 1.0000 Uiso R . . . . . . H331 H 0.4930 0.0832 0.1531 0.0368 1.0000 Uiso R . . . . . . H431 H 0.2505 0.0510 0.1242 0.0373 1.0000 Uiso R . . . . . . H531 H 0.1489 0.1623 0.0942 0.0369 1.0000 Uiso R . . . . . . H831 H 0.0977 0.3298 0.0626 0.0375 1.0000 Uiso R . . . . . . H931 H 0.1568 0.4721 0.0403 0.0382 1.0000 Uiso R . . . . . . H1031 H 0.3908 0.5705 0.0527 0.0379 1.0000 Uiso R . . . . . . H1131 H 0.5911 0.5329 0.0882 0.0370 1.0000 Uiso R . . . . . . H1531 H 0.8604 0.4725 0.1882 0.0344 1.0000 Uiso R . . . . . . H1631 H 1.1151 0.5218 0.1663 0.0343 1.0000 Uiso R . . . . . . H1731 H 1.1243 0.5026 0.1188 0.0337 1.0000 Uiso R . . . . . . H1831 H 0.8772 0.4344 0.0963 0.0343 1.0000 Uiso R . . . . . . H2031 H 0.4849 0.2946 0.2286 0.0366 1.0000 Uiso R . . . . . . H2032 H 0.3561 0.3783 0.2176 0.0366 1.0000 Uiso R . . . . . . H2033 H 0.3581 0.2781 0.2029 0.0366 1.0000 Uiso R . . . . . . H1141 H -0.1426 0.3560 0.2227 0.0362 1.0000 Uiso R . . . . . . H1041 H 0.0226 0.5024 0.2260 0.0363 1.0000 Uiso R . . . . . . H941 H 0.2623 0.5210 0.2571 0.0368 1.0000 Uiso R . . . . . . H841 H 0.3445 0.3918 0.2844 0.0367 1.0000 Uiso R . . . . . . H541 H 0.3758 0.2252 0.3143 0.0365 1.0000 Uiso R . . . . . . H441 H 0.3290 0.0783 0.3319 0.0363 1.0000 Uiso R . . . . . . H341 H 0.0980 -0.0232 0.3150 0.0363 1.0000 Uiso R . . . . . . H241 H -0.0969 0.0274 0.2801 0.0366 1.0000 Uiso R . . . . . . H1541 H -0.3555 0.1044 0.1828 0.0377 1.0000 Uiso R . . . . . . H1641 H -0.6275 0.0615 0.2069 0.0376 1.0000 Uiso R . . . . . . H1741 H -0.6485 0.0852 0.2518 0.0375 1.0000 Uiso R . . . . . . H1841 H -0.3929 0.1488 0.2742 0.0373 1.0000 Uiso R . . . . . . H2041 H 0.0134 0.2826 0.1447 0.0421 1.0000 Uiso R . . . . . . H2042 H 0.1277 0.3030 0.1714 0.0421 1.0000 Uiso R . . . . . . H2043 H 0.1470 0.2030 0.1569 0.0421 1.0000 Uiso R . . . . . . H251 H 0.0959 0.2697 0.4681 0.0296 1.0000 Uiso R . . . . . . H351 H -0.0583 0.4133 0.4742 0.0298 1.0000 Uiso R . . . . . . H451 H -0.2911 0.4294 0.5059 0.0303 1.0000 Uiso R . . . . . . H551 H -0.3782 0.3030 0.5324 0.0302 1.0000 Uiso R . . . . . . H851 H -0.4068 0.1296 0.5573 0.0300 1.0000 Uiso R . . . . . . H951 H -0.3592 -0.0100 0.5766 0.0303 1.0000 Uiso R . . . . . . H1051 H -0.1122 -0.1119 0.5606 0.0300 1.0000 Uiso R . . . . . . H1151 H 0.0793 -0.0605 0.5259 0.0297 1.0000 Uiso R . . . . . . H1551 H 0.3531 0.0420 0.4265 0.0291 1.0000 Uiso R . . . . . . H1651 H 0.6101 -0.0146 0.4520 0.0291 1.0000 Uiso R . . . . . . H1751 H 0.6037 -0.0114 0.4965 0.0294 1.0000 Uiso R . . . . . . H1851 H 0.3367 0.0476 0.5180 0.0295 1.0000 Uiso R . . . . . . H2051 H -0.0089 0.2248 0.3897 0.0322 1.0000 Uiso R . . . . . . H2052 H -0.1457 0.2328 0.4148 0.0322 1.0000 Uiso R . . . . . . H2053 H -0.1383 0.1372 0.3979 0.0322 1.0000 Uiso R . . . . . . H261 H 0.6112 0.0816 0.6405 0.0357 1.0000 Uiso R . . . . . . H361 H 0.4462 -0.0611 0.6408 0.0367 1.0000 Uiso R . . . . . . H461 H 0.2105 -0.0899 0.6106 0.0364 1.0000 Uiso R . . . . . . H561 H 0.1264 0.0216 0.5798 0.0361 1.0000 Uiso R . . . . . . H861 H 0.1074 0.1974 0.5471 0.0354 1.0000 Uiso R . . . . . . H961 H 0.1347 0.3479 0.5306 0.0357 1.0000 Uiso R . . . . . . H1061 H 0.3610 0.4481 0.5498 0.0359 1.0000 Uiso R . . . . . . H1161 H 0.5617 0.4008 0.5832 0.0354 1.0000 Uiso R . . . . . . H1561 H 0.8451 0.3660 0.6714 0.0325 1.0000 Uiso R . . . . . . H1661 H 1.1172 0.3861 0.6453 0.0326 1.0000 Uiso R . . . . . . H1761 H 1.1267 0.3242 0.6031 0.0327 1.0000 Uiso R . . . . . . H1861 H 0.8801 0.2468 0.5853 0.0335 1.0000 Uiso R . . . . . . H2061 H 0.4141 0.3186 0.7194 0.0343 1.0000 Uiso R . . . . . . H2062 H 0.3279 0.2390 0.7005 0.0343 1.0000 Uiso R . . . . . . H2063 H 0.2884 0.3482 0.6945 0.0343 1.0000 Uiso R . . . . . . H271 H -0.1244 0.0371 0.7774 0.0313 1.0000 Uiso R . . . . . . H371 H 0.0856 0.0080 0.8117 0.0321 1.0000 Uiso R . . . . . . H471 H 0.3159 0.1165 0.8223 0.0318 1.0000 Uiso R . . . . . . H571 H 0.3490 0.2545 0.7988 0.0318 1.0000 Uiso R . . . . . . H871 H 0.2875 0.4139 0.7644 0.0325 1.0000 Uiso R . . . . . . H971 H 0.1855 0.5177 0.7338 0.0327 1.0000 Uiso R . . . . . . H1071 H -0.0674 0.4804 0.7054 0.0327 1.0000 Uiso R . . . . . . H1171 H -0.2220 0.3316 0.7091 0.0324 1.0000 Uiso R . . . . . . H1571 H -0.4259 0.0521 0.6818 0.0345 1.0000 Uiso R . . . . . . H1671 H -0.6844 0.0371 0.7075 0.0343 1.0000 Uiso R . . . . . . H1771 H -0.6984 0.0875 0.7498 0.0341 1.0000 Uiso R . . . . . . H1871 H -0.4321 0.1576 0.7685 0.0339 1.0000 Uiso R . . . . . . H2071 H 0.0084 0.0931 0.6332 0.0379 1.0000 Uiso R . . . . . . H2072 H 0.1442 0.0744 0.6578 0.0379 1.0000 Uiso R . . . . . . H2073 H 0.0801 0.1797 0.6508 0.0379 1.0000 Uiso R . . . . . . H281 H 0.3811 0.4366 0.8320 0.0320 1.0000 Uiso R . . . . . . H381 H 0.5959 0.4655 0.7981 0.0330 1.0000 Uiso R . . . . . . H481 H 0.8259 0.3555 0.7877 0.0326 1.0000 Uiso R . . . . . . H581 H 0.8515 0.2153 0.8112 0.0326 1.0000 Uiso R . . . . . . H881 H 0.8109 0.0653 0.8495 0.0311 1.0000 Uiso R . . . . . . H981 H 0.6908 -0.0346 0.8834 0.0314 1.0000 Uiso R . . . . . . H1081 H 0.4320 0.0084 0.9071 0.0315 1.0000 Uiso R . . . . . . H1181 H 0.2760 0.1464 0.8986 0.0313 1.0000 Uiso R . . . . . . H1581 H 0.1137 0.4523 0.9235 0.0325 1.0000 Uiso R . . . . . . H1681 H -0.1766 0.4635 0.9009 0.0323 1.0000 Uiso R . . . . . . H1781 H -0.2054 0.3789 0.8602 0.0320 1.0000 Uiso R . . . . . . H1881 H 0.0429 0.2913 0.8435 0.0323 1.0000 Uiso R . . . . . . H2081 H 0.5369 0.4109 0.9706 0.0335 1.0000 Uiso R . . . . . . H2082 H 0.6247 0.3282 0.9529 0.0335 1.0000 Uiso R . . . . . . H2083 H 0.6611 0.4362 0.9451 0.0335 1.0000 Uiso R . . . . . . _refine_ls_extinction_method None #_oxford_refine_ls_scale 1.230(7) #loop_ # _oxford_twin_element_scale_factors # 0.842(6) # 0.158(6) 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 N11 . C121 . 1.478(12) yes N11 . C11 . 1.402(12) yes N11 . C131 . 1.362(12) yes O11 . C191 . 1.152(13) yes O21 . C191 . 1.352(13) yes O21 . C201 . 1.457(14) yes C121 . C111 . 1.279(13) yes C121 . C71 . 1.395(11) yes C111 . C101 . 1.305(13) yes C111 . H1111 . 0.950 no C101 . C91 . 1.361(13) yes C101 . H1011 . 0.950 no C91 . C81 . 1.332(13) yes C91 . H911 . 0.950 no C81 . C71 . 1.454(13) yes C81 . H811 . 0.950 no C71 . C61 . 1.474(12) yes C61 . C51 . 1.337(13) yes C61 . C11 . 1.446(11) yes C51 . C41 . 1.363(13) yes C51 . H511 . 0.950 no C41 . C31 . 1.382(13) yes C41 . H411 . 0.950 no C31 . C21 . 1.369(13) yes C31 . H311 . 0.950 no C21 . C11 . 1.381(13) yes C21 . H211 . 0.950 no C131 . C141 . 1.400(12) yes C131 . C181 . 1.453(13) yes C141 . C151 . 1.369(13) yes C141 . C191 . 1.460(12) yes C151 . C161 . 1.331(13) yes C151 . H1511 . 0.950 no C161 . C171 . 1.388(13) yes C161 . H1611 . 0.950 no C171 . C181 . 1.381(13) yes C171 . H1711 . 0.950 no C181 . H1811 . 0.950 no C201 . H2011 . 0.980 no C201 . H2012 . 0.980 no C201 . H2013 . 0.980 no N12 . C12 . 1.377(11) yes N12 . C122 . 1.433(11) yes N12 . C132 . 1.366(12) yes O12 . C192 . 1.250(13) yes O22 . C192 . 1.254(13) yes O22 . C202 . 1.463(14) yes C12 . C22 . 1.377(13) yes C12 . C62 . 1.421(11) yes C22 . C32 . 1.366(13) yes C22 . H221 . 0.950 no C32 . C42 . 1.382(13) yes C32 . H321 . 0.950 no C42 . C52 . 1.380(13) yes C42 . H421 . 0.950 no C52 . C62 . 1.368(13) yes C52 . H521 . 0.950 no C62 . C72 . 1.347(12) yes C72 . C82 . 1.456(13) yes C72 . C122 . 1.414(11) yes C82 . C92 . 1.392(13) yes C82 . H821 . 0.950 no C92 . C102 . 1.328(13) yes C92 . H921 . 0.950 no C102 . C112 . 1.392(13) yes C102 . H1021 . 0.950 no C112 . C122 . 1.349(13) yes C112 . H1121 . 0.950 no C132 . C142 . 1.345(12) yes C132 . C182 . 1.411(13) yes C142 . C152 . 1.370(13) yes C142 . C192 . 1.537(12) yes C152 . C162 . 1.317(13) yes C152 . H1521 . 0.950 no C162 . C172 . 1.382(13) yes C162 . H1621 . 0.950 no C172 . C182 . 1.407(13) yes C172 . H1721 . 0.950 no C182 . H1821 . 0.950 no C202 . H2021 . 0.980 no C202 . H2022 . 0.980 no C202 . H2023 . 0.980 no N13 . C13 . 1.395(11) yes N13 . C123 . 1.357(11) yes N13 . C133 . 1.414(12) yes O13 . C193 . 1.223(13) yes O23 . C193 . 1.350(13) yes O23 . C203 . 1.440(14) yes C13 . C23 . 1.370(13) yes C13 . C63 . 1.434(11) yes C23 . C33 . 1.372(13) yes C23 . H231 . 0.950 no C33 . C43 . 1.379(13) yes C33 . H331 . 0.950 no C43 . C53 . 1.360(13) yes C43 . H431 . 0.950 no C53 . C63 . 1.354(13) yes C53 . H531 . 0.950 no C63 . C73 . 1.408(12) yes C73 . C83 . 1.380(13) yes C73 . C123 . 1.455(11) yes C83 . C93 . 1.407(13) yes C83 . H831 . 0.950 no C93 . C103 . 1.343(13) yes C93 . H931 . 0.950 no C103 . C113 . 1.395(13) yes C103 . H1031 . 0.950 no C113 . C123 . 1.383(13) yes C113 . H1131 . 0.950 no C133 . C143 . 1.367(12) yes C133 . C183 . 1.444(13) yes C143 . C153 . 1.425(13) yes C143 . C193 . 1.423(12) yes C153 . C163 . 1.304(13) yes C153 . H1531 . 0.950 no C163 . C173 . 1.457(13) yes C163 . H1631 . 0.950 no C173 . C183 . 1.354(13) yes C173 . H1731 . 0.950 no C183 . H1831 . 0.950 no C203 . H2031 . 0.980 no C203 . H2032 . 0.980 no C203 . H2033 . 0.980 no N14 . C124 . 1.349(11) yes N14 . C14 . 1.378(12) yes N14 . C134 . 1.483(12) yes O14 . C194 . 1.225(13) yes O24 . C194 . 1.332(13) yes O24 . C204 . 1.408(14) yes C124 . C114 . 1.474(13) yes C124 . C74 . 1.415(11) yes C114 . C104 . 1.432(13) yes C114 . H1141 . 0.950 no C104 . C94 . 1.408(13) yes C104 . H1041 . 0.950 no C94 . C84 . 1.408(13) yes C94 . H941 . 0.950 no C84 . C74 . 1.318(13) yes C84 . H841 . 0.950 no C74 . C64 . 1.405(12) yes C64 . C54 . 1.452(13) yes C64 . C14 . 1.356(11) yes C54 . C44 . 1.365(13) yes C54 . H541 . 0.950 no C44 . C34 . 1.388(13) yes C44 . H441 . 0.950 no C34 . C24 . 1.386(13) yes C34 . H341 . 0.950 no C24 . C14 . 1.377(13) yes C24 . H241 . 0.950 no C134 . C144 . 1.354(12) yes C134 . C184 . 1.345(13) yes C144 . C154 . 1.406(13) yes C144 . C194 . 1.509(12) yes C154 . C164 . 1.413(13) yes C154 . H1541 . 0.950 no C164 . C174 . 1.347(13) yes C164 . H1641 . 0.950 no C174 . C184 . 1.373(13) yes C174 . H1741 . 0.950 no C184 . H1841 . 0.950 no C204 . H2041 . 0.980 no C204 . H2042 . 0.980 no C204 . H2043 . 0.980 no N15 . C15 . 1.391(11) yes N15 . C125 . 1.430(11) yes N15 . C135 . 1.422(12) yes O15 . C195 . 1.180(13) yes O25 . C195 . 1.290(13) yes O25 . C205 . 1.454(14) yes C15 . C25 . 1.383(13) yes C15 . C65 . 1.355(11) yes C25 . C35 . 1.376(13) yes C25 . H251 . 0.950 no C35 . C45 . 1.384(13) yes C35 . H351 . 0.950 no C45 . C55 . 1.362(13) yes C45 . H451 . 0.950 no C55 . C65 . 1.440(13) yes C55 . H551 . 0.950 no C65 . C75 . 1.460(12) yes C75 . C85 . 1.391(13) yes C75 . C125 . 1.345(11) yes C85 . C95 . 1.280(13) yes C85 . H851 . 0.950 no C95 . C105 . 1.460(13) yes C95 . H951 . 0.950 no C105 . C115 . 1.370(13) yes C105 . H1051 . 0.950 no C115 . C125 . 1.356(13) yes C115 . H1151 . 0.950 no C135 . C145 . 1.415(12) yes C135 . C185 . 1.299(13) yes C145 . C155 . 1.335(13) yes C145 . C195 . 1.557(12) yes C155 . C165 . 1.428(13) yes C155 . H1551 . 0.950 no C165 . C175 . 1.295(13) yes C165 . H1651 . 0.950 no C175 . C185 . 1.402(13) yes C175 . H1751 . 0.950 no C185 . H1851 . 0.950 no C205 . H2051 . 0.980 no C205 . H2052 . 0.980 no C205 . H2053 . 0.980 no N16 . C16 . 1.399(11) yes N16 . C126 . 1.324(11) yes N16 . C136 . 1.473(12) yes O16 . C196 . 1.131(13) yes O26 . C196 . 1.409(13) yes O26 . C206 . 1.441(14) yes C16 . C26 . 1.376(13) yes C16 . C66 . 1.393(11) yes C26 . C36 . 1.381(13) yes C26 . H261 . 0.950 no C36 . C46 . 1.379(13) yes C36 . H361 . 0.950 no C46 . C56 . 1.348(13) yes C46 . H461 . 0.950 no C56 . C66 . 1.409(13) yes C56 . H561 . 0.950 no C66 . C76 . 1.522(12) yes C76 . C86 . 1.357(13) yes C76 . C126 . 1.404(11) yes C86 . C96 . 1.331(13) yes C86 . H861 . 0.950 no C96 . C106 . 1.421(13) yes C96 . H961 . 0.950 no C106 . C116 . 1.371(13) yes C106 . H1061 . 0.950 no C116 . C126 . 1.382(13) yes C116 . H1161 . 0.950 no C136 . C146 . 1.462(12) yes C136 . C186 . 1.332(13) yes C146 . C156 . 1.404(13) yes C146 . C196 . 1.415(12) yes C156 . C166 . 1.417(13) yes C156 . H1561 . 0.950 no C166 . C176 . 1.361(13) yes C166 . H1661 . 0.950 no C176 . C186 . 1.326(13) yes C176 . H1761 . 0.950 no C186 . H1861 . 0.950 no C206 . H2061 . 0.980 no C206 . H2062 . 0.980 no C206 . H2063 . 0.980 no N17 . C17 . 1.388(11) yes N17 . C127 . 1.403(11) yes N17 . C137 . 1.442(12) yes O17 . C197 . 1.123(13) yes O27 . C197 . 1.353(13) yes O27 . C207 . 1.475(14) yes C17 . C27 . 1.372(13) yes C17 . C67 . 1.447(11) yes C27 . C37 . 1.369(13) yes C27 . H271 . 0.950 no C37 . C47 . 1.382(13) yes C37 . H371 . 0.950 no C47 . C57 . 1.359(13) yes C47 . H471 . 0.950 no C57 . C67 . 1.337(13) yes C57 . H571 . 0.950 no C67 . C77 . 1.442(12) yes C77 . C87 . 1.356(13) yes C77 . C127 . 1.403(11) yes C87 . C97 . 1.331(13) yes C87 . H871 . 0.950 no C97 . C107 . 1.429(13) yes C97 . H971 . 0.950 no C107 . C117 . 1.397(13) yes C107 . H1071 . 0.950 no C117 . C127 . 1.433(13) yes C117 . H1171 . 0.950 no C137 . C147 . 1.361(12) yes C137 . C187 . 1.410(13) yes C147 . C157 . 1.388(13) yes C147 . C197 . 1.498(12) yes C157 . C167 . 1.345(13) yes C157 . H1571 . 0.950 no C167 . C177 . 1.319(13) yes C167 . H1671 . 0.950 no C177 . C187 . 1.374(13) yes C177 . H1771 . 0.950 no C187 . H1871 . 0.950 no C207 . H2071 . 0.980 no C207 . H2072 . 0.980 no C207 . H2073 . 0.980 no N18 . C18 . 1.375(11) yes N18 . C128 . 1.365(11) yes N18 . C138 . 1.434(12) yes O18 . C198 . 1.237(13) yes O28 . C198 . 1.316(13) yes O28 . C208 . 1.392(14) yes C18 . C28 . 1.374(13) yes C18 . C68 . 1.357(11) yes C28 . C38 . 1.370(13) yes C28 . H281 . 0.950 no C38 . C48 . 1.390(13) yes C38 . H381 . 0.950 no C48 . C58 . 1.364(13) yes C48 . H481 . 0.950 no C58 . C68 . 1.437(13) yes C58 . H581 . 0.950 no C68 . C78 . 1.432(12) yes C78 . C88 . 1.423(13) yes C78 . C128 . 1.375(11) yes C88 . C98 . 1.403(13) yes C88 . H881 . 0.950 no C98 . C108 . 1.351(13) yes C98 . H981 . 0.950 no C108 . C118 . 1.351(13) yes C108 . H1081 . 0.950 no C118 . C128 . 1.331(13) yes C118 . H1181 . 0.950 no C138 . C148 . 1.391(12) yes C138 . C188 . 1.323(13) yes C148 . C158 . 1.409(13) yes C148 . C198 . 1.471(12) yes C158 . C168 . 1.401(13) yes C158 . H1581 . 0.950 no C168 . C178 . 1.421(13) yes C168 . H1681 . 0.950 no C178 . C188 . 1.388(13) yes C178 . H1781 . 0.950 no C188 . H1881 . 0.950 no C208 . H2081 . 0.980 no C208 . H2082 . 0.980 no C208 . H2083 . 0.980 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 C121 . N11 . C11 . 109.2(4) yes C121 . N11 . C131 . 124.0(5) yes C11 . N11 . C131 . 126.8(5) yes C191 . O21 . C201 . 118.4(7) yes N11 . C121 . C111 . 130.8(5) yes N11 . C121 . C71 . 105.2(5) yes C111 . C121 . C71 . 123.6(5) yes C121 . C111 . C101 . 117.4(6) yes C121 . C111 . H1111 . 121.2 no C101 . C111 . H1111 . 121.5 no C111 . C101 . C91 . 124.4(6) yes C111 . C101 . H1011 . 119.0 no C91 . C101 . H1011 . 116.6 no C101 . C91 . C81 . 122.1(6) yes C101 . C91 . H911 . 122.2 no C81 . C91 . H911 . 115.7 no C91 . C81 . C71 . 113.9(6) yes C91 . C81 . H811 . 123.7 no C71 . C81 . H811 . 122.4 no C81 . C71 . C121 . 118.6(5) yes C81 . C71 . C61 . 129.7(5) yes C121 . C71 . C61 . 111.6(5) yes C71 . C61 . C51 . 136.6(5) yes C71 . C61 . C11 . 104.2(4) yes C51 . C61 . C11 . 119.0(5) yes C61 . C51 . C41 . 120.3(6) yes C61 . C51 . H511 . 120.4 no C41 . C51 . H511 . 119.3 no C51 . C41 . C31 . 121.2(6) yes C51 . C41 . H411 . 122.6 no C31 . C41 . H411 . 116.2 no C41 . C31 . C21 . 121.3(6) yes C41 . C31 . H311 . 120.5 no C21 . C31 . H311 . 118.2 no C31 . C21 . C11 . 117.6(5) yes C31 . C21 . H211 . 121.0 no C11 . C21 . H211 . 121.4 no C61 . C11 . N11 . 109.6(5) yes C61 . C11 . C21 . 120.7(5) yes N11 . C11 . C21 . 129.6(5) yes N11 . C131 . C141 . 127.2(5) yes N11 . C131 . C181 . 116.1(6) yes C141 . C131 . C181 . 116.7(5) yes C131 . C141 . C151 . 119.9(5) yes C131 . C141 . C191 . 115.3(5) yes C151 . C141 . C191 . 124.5(6) yes C141 . C151 . C161 . 124.5(6) yes C141 . C151 . H1511 . 117.8 no C161 . C151 . H1511 . 117.7 no C151 . C161 . C171 . 118.0(6) yes C151 . C161 . H1611 . 121.1 no C171 . C161 . H1611 . 120.9 no C161 . C171 . C181 . 121.6(6) yes C161 . C171 . H1711 . 119.4 no C181 . C171 . H1711 . 119.0 no C131 . C181 . C171 . 119.4(6) yes C131 . C181 . H1811 . 120.1 no C171 . C181 . H1811 . 120.5 no C141 . C191 . O21 . 107.9(6) yes C141 . C191 . O11 . 134.4(6) yes O21 . C191 . O11 . 117.8(6) yes O21 . C201 . H2011 . 109.3 no O21 . C201 . H2012 . 108.4 no H2011 . C201 . H2012 . 109.5 no O21 . C201 . H2013 . 110.7 no H2011 . C201 . H2013 . 109.5 no H2012 . C201 . H2013 . 109.5 no C12 . N12 . C122 . 106.8(5) yes C12 . N12 . C132 . 128.9(5) yes C122 . N12 . C132 . 122.7(6) yes C192 . O22 . C202 . 117.2(7) yes N12 . C12 . C22 . 128.8(5) yes N12 . C12 . C62 . 109.4(5) yes C22 . C12 . C62 . 121.7(5) yes C12 . C22 . C32 . 117.9(6) yes C12 . C22 . H221 . 121.3 no C32 . C22 . H221 . 120.9 no C22 . C32 . C42 . 121.1(6) yes C22 . C32 . H321 . 119.6 no C42 . C32 . H321 . 119.2 no C32 . C42 . C52 . 121.3(6) yes C32 . C42 . H421 . 119.5 no C52 . C42 . H421 . 119.2 no C42 . C52 . C62 . 119.1(6) yes C42 . C52 . H521 . 120.5 no C62 . C52 . H521 . 120.4 no C12 . C62 . C52 . 118.8(5) yes C12 . C62 . C72 . 107.1(5) yes C52 . C62 . C72 . 134.1(5) yes C62 . C72 . C82 . 136.5(5) yes C62 . C72 . C122 . 110.3(5) yes C82 . C72 . C122 . 113.1(5) yes C72 . C82 . C92 . 118.3(6) yes C72 . C82 . H821 . 120.7 no C92 . C82 . H821 . 121.0 no C82 . C92 . C102 . 126.0(6) yes C82 . C92 . H921 . 116.8 no C102 . C92 . H921 . 117.3 no C92 . C102 . C112 . 117.0(6) yes C92 . C102 . H1021 . 121.3 no C112 . C102 . H1021 . 121.7 no C102 . C112 . C122 . 120.0(6) yes C102 . C112 . H1121 . 119.8 no C122 . C112 . H1121 . 120.2 no N12 . C122 . C72 . 106.0(5) yes N12 . C122 . C112 . 128.3(5) yes C72 . C122 . C112 . 125.6(5) yes N12 . C132 . C142 . 128.0(5) yes N12 . C132 . C182 . 116.6(6) yes C142 . C132 . C182 . 115.3(5) yes C132 . C142 . C152 . 122.6(5) yes C132 . C142 . C192 . 118.3(5) yes C152 . C142 . C192 . 119.0(5) yes C142 . C152 . C162 . 122.2(6) yes C142 . C152 . H1521 . 118.7 no C162 . C152 . H1521 . 119.1 no C152 . C162 . C172 . 120.3(6) yes C152 . C162 . H1621 . 119.6 no C172 . C162 . H1621 . 120.1 no C162 . C172 . C182 . 117.0(6) yes C162 . C172 . H1721 . 121.3 no C182 . C172 . H1721 . 121.7 no C132 . C182 . C172 . 122.6(6) yes C132 . C182 . H1821 . 118.9 no C172 . C182 . H1821 . 118.5 no C142 . C192 . O22 . 114.1(6) yes C142 . C192 . O12 . 122.1(6) yes O22 . C192 . O12 . 123.8(6) yes O22 . C202 . H2021 . 109.5 no O22 . C202 . H2022 . 108.2 no H2021 . C202 . H2022 . 109.5 no O22 . C202 . H2023 . 110.7 no H2021 . C202 . H2023 . 109.5 no H2022 . C202 . H2023 . 109.5 no C13 . N13 . C123 . 108.2(5) yes C13 . N13 . C133 . 124.1(5) yes C123 . N13 . C133 . 127.8(5) yes C193 . O23 . C203 . 118.5(7) yes N13 . C13 . C23 . 129.6(5) yes N13 . C13 . C63 . 109.2(5) yes C23 . C13 . C63 . 120.9(5) yes C13 . C23 . C33 . 117.7(6) yes C13 . C23 . H231 . 121.2 no C33 . C23 . H231 . 121.1 no C23 . C33 . C43 . 121.4(6) yes C23 . C33 . H331 . 119.4 no C43 . C33 . H331 . 119.3 no C33 . C43 . C53 . 121.2(6) yes C33 . C43 . H431 . 119.5 no C53 . C43 . H431 . 119.3 no C43 . C53 . C63 . 119.6(6) yes C43 . C53 . H531 . 120.1 no C63 . C53 . H531 . 120.2 no C13 . C63 . C53 . 119.2(5) yes C13 . C63 . C73 . 106.5(5) yes C53 . C63 . C73 . 134.2(5) yes C63 . C73 . C83 . 136.3(5) yes C63 . C73 . C123 . 106.4(5) yes C83 . C73 . C123 . 116.9(5) yes C73 . C83 . C93 . 119.4(6) yes C73 . C83 . H831 . 120.3 no C93 . C83 . H831 . 120.3 no C83 . C93 . C103 . 122.1(6) yes C83 . C93 . H931 . 119.0 no C103 . C93 . H931 . 118.9 no C93 . C103 . C113 . 121.9(6) yes C93 . C103 . H1031 . 119.1 no C113 . C103 . H1031 . 119.0 no C103 . C113 . C123 . 116.8(6) yes C103 . C113 . H1131 . 121.7 no C123 . C113 . H1131 . 121.5 no C73 . C123 . C113 . 122.8(5) yes C73 . C123 . N13 . 109.5(5) yes C113 . C123 . N13 . 127.6(5) yes N13 . C133 . C143 . 119.6(5) yes N13 . C133 . C183 . 118.7(6) yes C143 . C133 . C183 . 121.7(5) yes C133 . C143 . C153 . 116.7(5) yes C133 . C143 . C193 . 122.9(5) yes C153 . C143 . C193 . 120.3(6) yes C143 . C153 . C163 . 125.0(6) yes C143 . C153 . H1531 . 117.6 no C163 . C153 . H1531 . 117.3 no C153 . C163 . C173 . 117.2(6) yes C153 . C163 . H1631 . 121.6 no C173 . C163 . H1631 . 121.3 no C163 . C173 . C183 . 121.9(6) yes C163 . C173 . H1731 . 119.2 no C183 . C173 . H1731 . 119.0 no C133 . C183 . C173 . 117.5(6) yes C133 . C183 . H1831 . 121.1 no C173 . C183 . H1831 . 121.4 no C143 . C193 . O23 . 114.3(6) yes C143 . C193 . O13 . 128.4(6) yes O23 . C193 . O13 . 117.1(6) yes O23 . C203 . H2031 . 109.3 no O23 . C203 . H2032 . 110.2 no H2031 . C203 . H2032 . 109.5 no O23 . C203 . H2033 . 108.9 no H2031 . C203 . H2033 . 109.5 no H2032 . C203 . H2033 . 109.5 no C124 . N14 . C14 . 108.1(5) yes C124 . N14 . C134 . 125.9(5) yes C14 . N14 . C134 . 126.0(5) yes C194 . O24 . C204 . 115.0(7) yes N14 . C124 . C114 . 128.3(5) yes N14 . C124 . C74 . 110.6(5) yes C114 . C124 . C74 . 120.9(5) yes C124 . C114 . C104 . 116.7(5) yes C124 . C114 . H1141 . 122.1 no C104 . C114 . H1141 . 121.2 no C114 . C104 . C94 . 120.4(6) yes C114 . C104 . H1041 . 119.4 no C94 . C104 . H1041 . 120.2 no C104 . C94 . C84 . 118.2(6) yes C104 . C94 . H941 . 118.4 no C84 . C94 . H941 . 123.4 no C94 . C84 . C74 . 125.6(6) yes C94 . C84 . H841 . 117.1 no C74 . C84 . H841 . 117.3 no C124 . C74 . C84 . 118.2(5) yes C124 . C74 . C64 . 102.7(4) yes C84 . C74 . C64 . 138.8(6) yes C74 . C64 . C54 . 130.3(5) yes C74 . C64 . C14 . 111.1(5) yes C54 . C64 . C14 . 118.7(5) yes C64 . C54 . C44 . 117.8(6) yes C64 . C54 . H541 . 120.6 no C44 . C54 . H541 . 121.7 no C54 . C44 . C34 . 121.5(6) yes C54 . C44 . H441 . 116.5 no C34 . C44 . H441 . 121.9 no C44 . C34 . C24 . 121.0(6) yes C44 . C34 . H341 . 118.9 no C24 . C34 . H341 . 120.2 no C34 . C24 . C14 . 117.6(6) yes C34 . C24 . H241 . 121.3 no C14 . C24 . H241 . 121.1 no N14 . C14 . C24 . 129.2(5) yes N14 . C14 . C64 . 107.3(5) yes C24 . C14 . C64 . 123.5(5) yes N14 . C134 . C144 . 117.3(6) yes N14 . C134 . C184 . 119.9(6) yes C144 . C134 . C184 . 122.6(5) yes C134 . C144 . C154 . 118.8(5) yes C134 . C144 . C194 . 126.4(6) yes C154 . C144 . C194 . 114.7(6) yes C144 . C154 . C164 . 117.0(6) yes C144 . C154 . H1541 . 121.7 no C164 . C154 . H1541 . 121.3 no C154 . C164 . C174 . 122.4(6) yes C154 . C164 . H1641 . 119.0 no C174 . C164 . H1641 . 118.6 no C164 . C174 . C184 . 118.4(6) yes C164 . C174 . H1741 . 121.0 no C184 . C174 . H1741 . 120.6 no C174 . C184 . C134 . 120.7(6) yes C174 . C184 . H1841 . 119.9 no C134 . C184 . H1841 . 119.4 no C144 . C194 . O24 . 113.6(6) yes C144 . C194 . O14 . 119.6(6) yes O24 . C194 . O14 . 126.8(6) yes O24 . C204 . H2041 . 109.0 no O24 . C204 . H2042 . 109.8 no H2041 . C204 . H2042 . 109.5 no O24 . C204 . H2043 . 109.6 no H2041 . C204 . H2043 . 109.5 no H2042 . C204 . H2043 . 109.5 no C15 . N15 . C125 . 108.9(4) yes C15 . N15 . C135 . 128.0(5) yes C125 . N15 . C135 . 123.1(5) yes C195 . O25 . C205 . 114.6(7) yes N15 . C15 . C25 . 129.2(5) yes N15 . C15 . C65 . 107.4(5) yes C25 . C15 . C65 . 122.7(5) yes C15 . C25 . C35 . 117.7(6) yes C15 . C25 . H251 . 121.0 no C35 . C25 . H251 . 121.3 no C25 . C35 . C45 . 121.3(6) yes C25 . C35 . H351 . 119.2 no C45 . C35 . H351 . 119.5 no C35 . C45 . C55 . 121.2(6) yes C35 . C45 . H451 . 119.2 no C55 . C45 . H451 . 119.6 no C45 . C55 . C65 . 118.0(6) yes C45 . C55 . H551 . 120.8 no C65 . C55 . H551 . 121.2 no C55 . C65 . C15 . 119.1(5) yes C55 . C65 . C75 . 132.0(5) yes C15 . C65 . C75 . 108.6(5) yes C65 . C75 . C85 . 131.0(5) yes C65 . C75 . C125 . 107.4(5) yes C85 . C75 . C125 . 121.5(5) yes C75 . C85 . C95 . 120.1(6) yes C75 . C85 . H851 . 119.9 no C95 . C85 . H851 . 120.0 no C85 . C95 . C105 . 119.6(6) yes C85 . C95 . H951 . 120.2 no C105 . C95 . H951 . 120.3 no C95 . C105 . C115 . 119.5(6) yes C95 . C105 . H1051 . 120.2 no C115 . C105 . H1051 . 120.3 no C105 . C115 . C125 . 118.5(6) yes C105 . C115 . H1151 . 120.7 no C125 . C115 . H1151 . 120.8 no N15 . C125 . C115 . 131.6(5) yes N15 . C125 . C75 . 107.6(5) yes C115 . C125 . C75 . 120.8(5) yes N15 . C135 . C145 . 122.5(5) yes N15 . C135 . C185 . 119.2(6) yes C145 . C135 . C185 . 118.3(5) yes C135 . C145 . C155 . 120.8(5) yes C135 . C145 . C195 . 120.7(5) yes C155 . C145 . C195 . 118.3(6) yes C145 . C155 . C165 . 117.5(6) yes C145 . C155 . H1551 . 121.4 no C165 . C155 . H1551 . 121.1 no C155 . C165 . C175 . 122.2(6) yes C155 . C165 . H1651 . 119.1 no C175 . C165 . H1651 . 118.7 no C165 . C175 . C185 . 118.0(6) yes C165 . C175 . H1751 . 121.3 no C185 . C175 . H1751 . 120.7 no C175 . C185 . C135 . 123.2(6) yes C175 . C185 . H1851 . 118.7 no C135 . C185 . H1851 . 118.1 no C145 . C195 . O25 . 108.0(6) yes C145 . C195 . O15 . 120.3(6) yes O25 . C195 . O15 . 131.6(6) yes O25 . C205 . H2051 . 109.7 no O25 . C205 . H2052 . 110.9 no H2051 . C205 . H2052 . 109.5 no O25 . C205 . H2053 . 107.8 no H2051 . C205 . H2053 . 109.5 no H2052 . C205 . H2053 . 109.5 no C16 . N16 . C126 . 109.6(5) yes C16 . N16 . C136 . 123.5(5) yes C126 . N16 . C136 . 126.8(5) yes C196 . O26 . C206 . 114.9(7) yes N16 . C16 . C26 . 129.7(5) yes N16 . C16 . C66 . 108.6(5) yes C26 . C16 . C66 . 121.6(5) yes C16 . C26 . C36 . 117.5(6) yes C16 . C26 . H261 . 121.3 no C36 . C26 . H261 . 121.2 no C26 . C36 . C46 . 121.5(6) yes C26 . C36 . H361 . 119.4 no C46 . C36 . H361 . 119.1 no C36 . C46 . C56 . 121.3(6) yes C36 . C46 . H461 . 119.5 no C56 . C46 . H461 . 119.2 no C46 . C56 . C66 . 118.8(6) yes C46 . C56 . H561 . 120.7 no C66 . C56 . H561 . 120.6 no C56 . C66 . C16 . 119.2(5) yes C56 . C66 . C76 . 134.8(5) yes C16 . C66 . C76 . 106.0(5) yes C66 . C76 . C86 . 135.1(5) yes C66 . C76 . C126 . 103.2(5) yes C86 . C76 . C126 . 121.4(5) yes C76 . C86 . C96 . 121.5(6) yes C76 . C86 . H861 . 119.4 no C96 . C86 . H861 . 119.1 no C86 . C96 . C106 . 116.4(6) yes C86 . C96 . H961 . 122.1 no C106 . C96 . H961 . 121.5 no C96 . C106 . C116 . 125.2(6) yes C96 . C106 . H1061 . 117.7 no C116 . C106 . H1061 . 117.1 no C106 . C116 . C126 . 115.4(6) yes C106 . C116 . H1161 . 122.5 no C126 . C116 . H1161 . 122.2 no C76 . C126 . C116 . 120.2(5) yes C76 . C126 . N16 . 112.1(5) yes C116 . C126 . N16 . 127.7(5) yes N16 . C136 . C146 . 114.6(6) yes N16 . C136 . C186 . 119.7(6) yes C146 . C136 . C186 . 124.8(5) yes C136 . C146 . C156 . 112.4(5) yes C136 . C146 . C196 . 122.7(5) yes C156 . C146 . C196 . 124.6(5) yes C146 . C156 . C166 . 121.9(6) yes C146 . C156 . H1561 . 119.1 no C166 . C156 . H1561 . 119.0 no C156 . C166 . C176 . 118.8(6) yes C156 . C166 . H1661 . 120.6 no C176 . C166 . H1661 . 120.6 no C166 . C176 . C186 . 122.9(6) yes C166 . C176 . H1761 . 118.6 no C186 . C176 . H1761 . 118.5 no C136 . C186 . C176 . 119.2(6) yes C136 . C186 . H1861 . 120.4 no C176 . C186 . H1861 . 120.4 no C146 . C196 . O26 . 108.5(6) yes C146 . C196 . O16 . 130.3(6) yes O26 . C196 . O16 . 121.1(6) yes O26 . C206 . H2061 . 109.5 no O26 . C206 . H2062 . 110.2 no H2061 . C206 . H2062 . 109.5 no O26 . C206 . H2063 . 108.6 no H2061 . C206 . H2063 . 109.5 no H2062 . C206 . H2063 . 109.5 no C17 . N17 . C127 . 107.7(5) yes C17 . N17 . C137 . 122.8(5) yes C127 . N17 . C137 . 129.1(5) yes C197 . O27 . C207 . 111.9(7) yes N17 . C17 . C27 . 129.6(5) yes N17 . C17 . C67 . 109.5(5) yes C27 . C17 . C67 . 120.8(5) yes C17 . C27 . C37 . 117.6(6) yes C17 . C27 . H271 . 121.3 no C37 . C27 . H271 . 121.1 no C27 . C37 . C47 . 121.3(6) yes C27 . C37 . H371 . 119.5 no C47 . C37 . H371 . 119.3 no C37 . C47 . C57 . 121.3(6) yes C37 . C47 . H471 . 119.4 no C57 . C47 . H471 . 119.3 no C47 . C57 . C67 . 120.1(6) yes C47 . C57 . H571 . 120.0 no C67 . C57 . H571 . 119.9 no C17 . C67 . C57 . 119.0(5) yes C17 . C67 . C77 . 105.3(5) yes C57 . C67 . C77 . 135.6(5) yes C67 . C77 . C87 . 136.0(5) yes C67 . C77 . C127 . 107.8(5) yes C87 . C77 . C127 . 116.2(5) yes C77 . C87 . C97 . 123.1(6) yes C77 . C87 . H871 . 118.5 no C97 . C87 . H871 . 118.4 no C87 . C97 . C107 . 120.9(6) yes C87 . C97 . H971 . 119.6 no C107 . C97 . H971 . 119.5 no C97 . C107 . C117 . 121.0(6) yes C97 . C107 . H1071 . 119.6 no C117 . C107 . H1071 . 119.5 no C107 . C117 . C127 . 113.5(6) yes C107 . C117 . H1171 . 123.3 no C127 . C117 . H1171 . 123.2 no C117 . C127 . N17 . 124.9(5) yes C117 . C127 . C77 . 125.4(5) yes N17 . C127 . C77 . 109.5(5) yes N17 . C137 . C147 . 124.0(5) yes N17 . C137 . C187 . 114.6(6) yes C147 . C137 . C187 . 121.2(5) yes C137 . C147 . C157 . 117.0(5) yes C137 . C147 . C197 . 118.4(5) yes C157 . C147 . C197 . 124.6(5) yes C147 . C157 . C167 . 120.3(6) yes C147 . C157 . H1571 . 119.7 no C167 . C157 . H1571 . 120.0 no C157 . C167 . C177 . 124.2(6) yes C157 . C167 . H1671 . 117.7 no C177 . C167 . H1671 . 118.1 no C167 . C177 . C187 . 117.9(6) yes C167 . C177 . H1771 . 120.8 no C187 . C177 . H1771 . 121.2 no C137 . C187 . C177 . 119.4(6) yes C137 . C187 . H1871 . 120.5 no C177 . C187 . H1871 . 120.1 no C147 . C197 . O27 . 106.3(5) yes C147 . C197 . O17 . 126.7(6) yes O27 . C197 . O17 . 126.8(6) yes O27 . C207 . H2071 . 109.6 no O27 . C207 . H2072 . 108.6 no H2071 . C207 . H2072 . 109.5 no O27 . C207 . H2073 . 110.2 no H2071 . C207 . H2073 . 109.5 no H2072 . C207 . H2073 . 109.5 no C18 . N18 . C128 . 109.6(5) yes C18 . N18 . C138 . 126.1(5) yes C128 . N18 . C138 . 123.4(5) yes C198 . O28 . C208 . 120.0(7) yes N18 . C18 . C28 . 129.3(5) yes N18 . C18 . C68 . 107.2(5) yes C28 . C18 . C68 . 123.2(5) yes C18 . C28 . C38 . 117.6(6) yes C18 . C28 . H281 . 121.1 no C38 . C28 . H281 . 121.3 no C28 . C38 . C48 . 121.1(6) yes C28 . C38 . H381 . 119.3 no C48 . C38 . H381 . 119.6 no C38 . C48 . C58 . 121.4(6) yes C38 . C48 . H481 . 119.2 no C58 . C48 . H481 . 119.4 no C48 . C58 . C68 . 117.5(6) yes C48 . C58 . H581 . 121.1 no C68 . C58 . H581 . 121.4 no C58 . C68 . C18 . 119.1(5) yes C58 . C68 . C78 . 132.6(5) yes C18 . C68 . C78 . 108.4(5) yes C68 . C78 . C88 . 133.6(5) yes C68 . C78 . C128 . 105.9(5) yes C88 . C78 . C128 . 120.5(5) yes C78 . C88 . C98 . 115.6(6) yes C78 . C88 . H881 . 122.0 no C98 . C88 . H881 . 122.5 no C88 . C98 . C108 . 121.0(6) yes C88 . C98 . H981 . 119.2 no C108 . C98 . H981 . 119.8 no C98 . C108 . C118 . 122.0(6) yes C98 . C108 . H1081 . 118.7 no C118 . C108 . H1081 . 119.3 no C108 . C118 . C128 . 119.7(6) yes C108 . C118 . H1181 . 119.9 no C128 . C118 . H1181 . 120.4 no C78 . C128 . N18 . 108.3(5) yes C78 . C128 . C118 . 121.3(5) yes N18 . C128 . C118 . 130.3(5) yes N18 . C138 . C148 . 119.2(6) yes N18 . C138 . C188 . 119.3(6) yes C148 . C138 . C188 . 121.2(5) yes C138 . C148 . C158 . 119.1(5) yes C138 . C148 . C198 . 124.6(5) yes C158 . C148 . C198 . 116.2(5) yes C148 . C158 . C168 . 121.1(6) yes C148 . C158 . H1581 . 119.6 no C168 . C158 . H1581 . 119.3 no C158 . C168 . C178 . 116.2(6) yes C158 . C168 . H1681 . 122.1 no C178 . C168 . H1681 . 121.7 no C168 . C178 . C188 . 121.5(6) yes C168 . C178 . H1781 . 119.4 no C188 . C178 . H1781 . 119.0 no C178 . C188 . C138 . 120.9(6) yes C178 . C188 . H1881 . 119.7 no C138 . C188 . H1881 . 119.4 no C148 . C198 . O28 . 116.9(6) yes C148 . C198 . O18 . 124.5(6) yes O28 . C198 . O18 . 117.9(6) yes O28 . C208 . H2081 . 109.4 no O28 . C208 . H2082 . 108.8 no H2081 . C208 . H2082 . 109.5 no O28 . C208 . H2083 . 110.1 no H2081 . C208 . H2083 . 109.5 no H2082 . C208 . H2083 . 109.5 no _chemical_name_common 'Methyl 2-(9H-carbazol-9-yl)benzoate' _exptl_crystal_recrystallization_method ; A mixture of carbazole, methyl 2-iodobenzoate, copper powder, potassium carbonate and nitrobenzene were heated at 175 degrees C for 48 h. After cooling, the resultant mixture was a red solid. A mixture of water/chloroform (1:1) was added to the solid, and the two layers separated. The aqueous layer was then extracted twice with chloroform, and the organic layers were combined and dried over MgSO4. The solvent was removed under reduced pressure, and the residue oil was purified by flash dry chromatography on silica using hexane/ethyl acetate (85:15) as the eluant. This resulted in the formation of colourless crystals. (5.30 g, 88%) ; #edit data_4_9GPa_I.cif _database_code_depnum_ccdc_archive 'CCDC 752559' #_oxford_structure_analysis_title 'mben08 in Pn' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 7.0316(6) _cell_length_b 14.0254(19) _cell_length_c 50.157(8) _cell_angle_alpha 90 _cell_angle_beta 89.796(9) _cell_angle_gamma 90 _cell_volume 4946.5(11) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 n 1 ' _symmetry_space_group_name_Hall 'P -2yac' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y,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 0.0000 0.0010 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0010 0.0010 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0030 0.0030 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 16 # Given Formula = C20 H15 N1 O2 # Dc = 1.62 Fooo = 2528.00 Mu = 1.05 M = 2410.76 # Found Formula = C20 H15 N1 O2 # Dc = 1.62 FOOO = 2528.00 Mu = 1.05 M = 2410.76 _chemical_formula_sum 'C20 H15 N1 O2' _chemical_formula_moiety 'C20 H15 N1 O2' _chemical_compound_source ? _chemical_formula_weight 301.34 _cell_measurement_reflns_used 3130 _cell_measurement_theta_min 2 _cell_measurement_theta_max 13 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.618 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 2528 _exptl_absorpt_coefficient_mu 0.105 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device APEX-II _diffrn_measurement_device_type Area _diffrn_radiation_monochromator silicon _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.47620 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 293 _diffrn_ambient_pressure 4900000 _diffrn_reflns_number 15990 _reflns_number_total 3698 _diffrn_reflns_av_R_equivalents 0.1028 # Number of reflections with Friedels Law is 3698 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5082 _diffrn_reflns_reduction_process ; Merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 ; _diffrn_reflns_theta_min 1.010 _diffrn_reflns_theta_max 13.649 _diffrn_measured_fraction_theta_max 0.734 _diffrn_reflns_theta_full 10.373 _diffrn_measured_fraction_theta_full 0.774 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 44 _reflns_limit_h_min -6 _reflns_limit_h_max 6 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 44 #_oxford_diffrn_Wilson_B_factor 0.00 #_oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.17 _refine_diff_density_max 0.15 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement #_oxford_reflns_threshold_expression_ref I>2.0\s(I) _refine_ls_number_reflns 3201 _refine_ls_number_restraints 1154 _refine_ls_number_parameters 738 #_oxford_refine_ls_R_factor_ref 0.0767 _refine_ls_wR_factor_ref 0.0762 _refine_ls_goodness_of_fit_ref 0.9230 _refine_ls_shift/su_max 0.004643 # The values computed from all data #_oxford_reflns_number_all 3673 _refine_ls_R_factor_all 0.0906 _refine_ls_wR_factor_all 0.0901 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3201 _refine_ls_R_factor_gt 0.0767 _refine_ls_wR_factor_gt 0.0762 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 11.3 -8.50 5.81 ; 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens N11 N -0.0719(18) 0.6832(8) -0.1388(3) 0.0264(19) 1.0000 Uiso D U . . . . . O11 O 0.0995(17) 0.6668(11) -0.0857(3) 0.026(3) 1.0000 Uiso D U . . . . . O21 O -0.1131(15) 0.7251(11) -0.0591(3) 0.027(2) 1.0000 Uiso D U . . . . . C121 C 0.0209(15) 0.7763(7) -0.1347(2) 0.027(2) 1.0000 Uiso D U . . . . . C111 C -0.0259(17) 0.8473(9) -0.1198(2) 0.027(2) 1.0000 Uiso D U . . . . . C101 C 0.0660(19) 0.9276(9) -0.1234(3) 0.027(3) 1.0000 Uiso D U . . . . . C91 C 0.2077(18) 0.9399(9) -0.1418(3) 0.027(3) 1.0000 Uiso D U . . . . . C81 C 0.2654(17) 0.8694(10) -0.1578(2) 0.028(2) 1.0000 Uiso D U . . . . . C71 C 0.1647(16) 0.7804(8) -0.1540(2) 0.027(2) 1.0000 Uiso D U . . . . . C61 C 0.1744(16) 0.6924(8) -0.1698(2) 0.027(2) 1.0000 Uiso D U . . . . . C51 C 0.2787(17) 0.6598(10) -0.1903(3) 0.028(2) 1.0000 Uiso D U . . . . . C41 C 0.2413(18) 0.5730(10) -0.2010(3) 0.028(3) 1.0000 Uiso D U . . . . . C31 C 0.0979(19) 0.5161(9) -0.1908(3) 0.028(3) 1.0000 Uiso D U . . . . . C21 C -0.0136(17) 0.5455(9) -0.1700(3) 0.028(2) 1.0000 Uiso D U . . . . . C11 C 0.0238(15) 0.6335(7) -0.1592(2) 0.027(2) 1.0000 Uiso D U . . . . . C131 C -0.2202(14) 0.6511(8) -0.1239(2) 0.026(2) 1.0000 Uiso D U . . . . . C141 C -0.2331(14) 0.6503(8) -0.0960(2) 0.025(2) 1.0000 Uiso D U . . . . . C151 C -0.3908(18) 0.6129(9) -0.0838(3) 0.025(2) 1.0000 Uiso D U . . . . . C161 C -0.5396(17) 0.5774(9) -0.0968(3) 0.025(3) 1.0000 Uiso D U . . . . . C171 C -0.5357(17) 0.5783(9) -0.1245(3) 0.026(3) 1.0000 Uiso D U . . . . . C181 C -0.3820(18) 0.6139(9) -0.1384(3) 0.026(2) 1.0000 Uiso D U . . . . . C191 C -0.0609(14) 0.6793(13) -0.0820(3) 0.026(2) 1.0000 Uiso D U . . . . . C201 C 0.036(2) 0.7617(16) -0.0419(4) 0.028(3) 1.0000 Uiso D U . . . . . N12 N 0.0947(15) 0.3036(7) 0.0027(2) 0.0244(19) 1.0000 Uiso D U . . . . . O12 O -0.1071(17) 0.2449(11) -0.0393(3) 0.030(3) 1.0000 Uiso D U . . . . . O22 O 0.0580(15) 0.1849(11) -0.0727(3) 0.028(2) 1.0000 Uiso D U . . . . . C12 C 0.0166(15) 0.3880(7) -0.0061(2) 0.025(2) 1.0000 Uiso D U . . . . . C22 C 0.0804(16) 0.4479(9) -0.0257(3) 0.026(2) 1.0000 Uiso D U . . . . . C32 C -0.0193(19) 0.5298(9) -0.0302(3) 0.026(3) 1.0000 Uiso D U . . . . . C42 C -0.1781(18) 0.5525(9) -0.0152(3) 0.026(3) 1.0000 Uiso D U . . . . . C52 C -0.2432(16) 0.4926(9) 0.0045(3) 0.026(2) 1.0000 Uiso D U . . . . . C62 C -0.1466(15) 0.4099(8) 0.0095(2) 0.025(2) 1.0000 Uiso D U . . . . . C72 C -0.1682(15) 0.3381(8) 0.0274(2) 0.025(2) 1.0000 Uiso D U . . . . . C82 C -0.2978(17) 0.3153(9) 0.0493(3) 0.026(2) 1.0000 Uiso D U . . . . . C92 C -0.2743(18) 0.2293(10) 0.0624(2) 0.027(3) 1.0000 Uiso D U . . . . . C102 C -0.1430(19) 0.1634(9) 0.0568(3) 0.027(3) 1.0000 Uiso D U . . . . . C112 C -0.0160(17) 0.1834(9) 0.0362(3) 0.026(2) 1.0000 Uiso D U . . . . . C122 C -0.0296(15) 0.2667(7) 0.0228(2) 0.025(2) 1.0000 Uiso D U . . . . . C132 C 0.2329(14) 0.2498(8) -0.0091(2) 0.025(2) 1.0000 Uiso D U . . . . . C142 C 0.2261(14) 0.2058(8) -0.0329(2) 0.025(2) 1.0000 Uiso D U . . . . . C152 C 0.3768(18) 0.1566(9) -0.0431(2) 0.024(2) 1.0000 Uiso D U . . . . . C162 C 0.5394(18) 0.1498(9) -0.0305(3) 0.024(3) 1.0000 Uiso D U . . . . . C172 C 0.5630(17) 0.1925(9) -0.0059(3) 0.024(3) 1.0000 Uiso D U . . . . . C182 C 0.4074(18) 0.2426(9) 0.0045(2) 0.025(2) 1.0000 Uiso D U . . . . . C192 C 0.0425(16) 0.2131(16) -0.0491(3) 0.027(2) 1.0000 Uiso D U . . . . . C202 C -0.115(2) 0.1841(17) -0.0888(4) 0.028(3) 1.0000 Uiso D U . . . . . N13 N 0.5631(17) 0.3725(7) 0.1169(2) 0.0245(19) 1.0000 Uiso D U . . . . . O13 O 0.3789(16) 0.4107(10) 0.1682(3) 0.026(3) 1.0000 Uiso D U . . . . . O23 O 0.5906(15) 0.3529(10) 0.1961(3) 0.024(2) 1.0000 Uiso D U . . . . . C13 C 0.4829(15) 0.2841(7) 0.1235(2) 0.025(2) 1.0000 Uiso D U . . . . . C23 C 0.5429(17) 0.2163(9) 0.1414(2) 0.025(2) 1.0000 Uiso D U . . . . . C33 C 0.4512(19) 0.1296(9) 0.1412(3) 0.026(3) 1.0000 Uiso D U . . . . . C43 C 0.3052(19) 0.1112(9) 0.1236(3) 0.026(3) 1.0000 Uiso D U . . . . . C53 C 0.2440(17) 0.1784(9) 0.1063(3) 0.026(2) 1.0000 Uiso D U . . . . . C63 C 0.3293(15) 0.2648(7) 0.1057(2) 0.025(2) 1.0000 Uiso D U . . . . . C73 C 0.3092(15) 0.3456(7) 0.0895(2) 0.026(2) 1.0000 Uiso D U . . . . . C83 C 0.1941(17) 0.3717(9) 0.0687(3) 0.027(3) 1.0000 Uiso D U . . . . . C93 C 0.2294(19) 0.4571(10) 0.0551(3) 0.027(3) 1.0000 Uiso D U . . . . . C103 C 0.373(2) 0.5153(9) 0.0619(3) 0.026(3) 1.0000 Uiso D U . . . . . C113 C 0.4956(17) 0.4941(9) 0.0829(3) 0.025(2) 1.0000 Uiso D U . . . . . C123 C 0.4616(15) 0.4100(7) 0.0965(2) 0.025(2) 1.0000 Uiso D U . . . . . C133 C 0.7175(14) 0.4144(8) 0.1305(2) 0.024(2) 1.0000 Uiso D U . . . . . C143 C 0.7088(14) 0.4254(8) 0.1576(2) 0.023(2) 1.0000 Uiso D U . . . . . C153 C 0.8685(18) 0.4681(9) 0.1700(2) 0.023(2) 1.0000 Uiso D U . . . . . C163 C 1.0198(17) 0.4980(9) 0.1575(3) 0.024(3) 1.0000 Uiso D U . . . . . C173 C 1.0250(17) 0.4861(9) 0.1288(3) 0.024(3) 1.0000 Uiso D U . . . . . C183 C 0.8799(18) 0.4457(9) 0.1153(2) 0.024(2) 1.0000 Uiso D U . . . . . C193 C 0.5474(13) 0.3980(13) 0.1731(3) 0.025(2) 1.0000 Uiso D U . . . . . C203 C 0.437(2) 0.3182(16) 0.2124(4) 0.026(3) 1.0000 Uiso D U . . . . . N14 N -0.0673(17) 0.2006(7) 0.2569(3) 0.027(2) 1.0000 Uiso D U . . . . . O14 O 0.1187(17) 0.1634(12) 0.2068(3) 0.036(3) 1.0000 Uiso D U . . . . . O24 O -0.0904(16) 0.2225(11) 0.1765(3) 0.034(3) 1.0000 Uiso D U . . . . . C124 C 0.0192(15) 0.2857(7) 0.2526(2) 0.028(2) 1.0000 Uiso D U . . . . . C114 C -0.0391(17) 0.3628(10) 0.2347(2) 0.027(2) 1.0000 Uiso D U . . . . . C104 C 0.0605(19) 0.4514(9) 0.2373(3) 0.028(3) 1.0000 Uiso D U . . . . . C94 C 0.2069(19) 0.4615(9) 0.2561(3) 0.028(3) 1.0000 Uiso D U . . . . . C84 C 0.2533(17) 0.3829(10) 0.2719(3) 0.028(2) 1.0000 Uiso D U . . . . . C74 C 0.1685(16) 0.2993(8) 0.2711(2) 0.028(2) 1.0000 Uiso D U . . . . . C64 C 0.1665(16) 0.2137(8) 0.2857(2) 0.027(2) 1.0000 Uiso D U . . . . . C54 C 0.2838(17) 0.1834(9) 0.3078(3) 0.027(3) 1.0000 Uiso D U . . . . . C44 C 0.2527(19) 0.0949(10) 0.3181(3) 0.028(3) 1.0000 Uiso D U . . . . . C34 C 0.113(2) 0.0351(9) 0.3080(3) 0.027(3) 1.0000 Uiso D U . . . . . C24 C -0.0015(18) 0.0640(9) 0.2872(3) 0.028(2) 1.0000 Uiso D U . . . . . C14 C 0.0309(15) 0.1535(7) 0.2766(2) 0.027(2) 1.0000 Uiso D U . . . . . C134 C -0.2322(14) 0.1621(8) 0.2420(2) 0.028(2) 1.0000 Uiso D U . . . . . C144 C -0.2117(14) 0.1503(8) 0.2154(2) 0.030(2) 1.0000 Uiso D U . . . . . C154 C -0.3630(18) 0.1112(9) 0.2008(3) 0.030(2) 1.0000 Uiso D U . . . . . C164 C -0.5266(18) 0.0839(9) 0.2153(3) 0.029(3) 1.0000 Uiso D U . . . . . C174 C -0.5409(17) 0.0955(9) 0.2419(3) 0.029(3) 1.0000 Uiso D U . . . . . C184 C -0.3898(18) 0.1348(9) 0.2553(3) 0.029(2) 1.0000 Uiso D U . . . . . C194 C -0.0431(14) 0.1802(14) 0.1989(3) 0.033(2) 1.0000 Uiso D U . . . . . C204 C 0.063(2) 0.2585(17) 0.1615(4) 0.034(3) 1.0000 Uiso D U . . . . . N15 N 0.0392(17) 0.1096(8) 0.5010(3) 0.0246(19) 1.0000 Uiso D U . . . . . O15 O -0.1298(17) 0.0895(11) 0.4495(3) 0.027(3) 1.0000 Uiso D U . . . . . O25 O 0.0882(15) 0.1511(11) 0.4210(3) 0.025(2) 1.0000 Uiso D U . . . . . C15 C -0.0514(15) 0.1968(7) 0.4974(2) 0.025(2) 1.0000 Uiso D U . . . . . C25 C -0.0014(16) 0.2722(9) 0.4811(2) 0.025(2) 1.0000 Uiso D U . . . . . C35 C -0.0959(18) 0.3569(9) 0.4846(3) 0.025(3) 1.0000 Uiso D U . . . . . C45 C -0.2371(18) 0.3666(9) 0.5038(3) 0.026(3) 1.0000 Uiso D U . . . . . C55 C -0.2899(17) 0.2918(9) 0.5195(2) 0.026(2) 1.0000 Uiso D U . . . . . C65 C -0.1925(15) 0.2028(7) 0.5160(2) 0.025(2) 1.0000 Uiso D U . . . . . C75 C -0.1976(15) 0.1137(7) 0.5310(2) 0.025(2) 1.0000 Uiso D U . . . . . C85 C -0.3142(17) 0.0836(9) 0.5519(3) 0.026(2) 1.0000 Uiso D U . . . . . C95 C -0.2848(18) 0.0021(10) 0.5630(2) 0.026(3) 1.0000 Uiso D U . . . . . C105 C -0.1314(19) -0.0584(9) 0.5534(3) 0.026(3) 1.0000 Uiso D U . . . . . C115 C -0.0184(17) -0.0276(9) 0.5327(3) 0.025(2) 1.0000 Uiso D U . . . . . C125 C -0.0543(15) 0.0586(7) 0.5218(2) 0.025(2) 1.0000 Uiso D U . . . . . C135 C 0.1966(14) 0.0720(8) 0.4863(2) 0.024(2) 1.0000 Uiso D U . . . . . C145 C 0.2027(14) 0.0727(8) 0.4583(2) 0.024(2) 1.0000 Uiso D U . . . . . C155 C 0.3543(18) 0.0393(9) 0.4451(3) 0.024(2) 1.0000 Uiso D U . . . . . C165 C 0.5091(17) 0.0038(9) 0.4605(3) 0.024(3) 1.0000 Uiso D U . . . . . C175 C 0.5063(17) 0.0032(9) 0.4863(3) 0.024(3) 1.0000 Uiso D U . . . . . C185 C 0.3438(18) 0.0386(9) 0.4992(2) 0.024(2) 1.0000 Uiso D U . . . . . C195 C 0.0270(14) 0.1053(13) 0.4417(3) 0.025(2) 1.0000 Uiso D U . . . . . C205 C -0.060(2) 0.1872(16) 0.4037(4) 0.028(3) 1.0000 Uiso D U . . . . . N16 N 0.5415(16) 0.2232(7) 0.6042(3) 0.0275(19) 1.0000 Uiso D U . . . . . O16 O 0.3722(18) 0.2592(12) 0.6515(3) 0.033(3) 1.0000 Uiso D U . . . . . O26 O 0.5495(16) 0.3081(11) 0.6850(2) 0.030(2) 1.0000 Uiso D U . . . . . C16 C 0.4607(15) 0.1336(7) 0.6093(2) 0.028(2) 1.0000 Uiso D U . . . . . C26 C 0.5065(17) 0.0666(9) 0.6282(3) 0.029(2) 1.0000 Uiso D U . . . . . C36 C 0.405(2) -0.0178(9) 0.6280(3) 0.031(3) 1.0000 Uiso D U . . . . . C46 C 0.2640(19) -0.0341(9) 0.6097(3) 0.032(3) 1.0000 Uiso D U . . . . . C56 C 0.2167(17) 0.0314(10) 0.5915(3) 0.031(2) 1.0000 Uiso D U . . . . . C66 C 0.3153(16) 0.1184(8) 0.5911(2) 0.029(2) 1.0000 Uiso D U . . . . . C76 C 0.3061(16) 0.2076(8) 0.5740(2) 0.028(2) 1.0000 Uiso D U . . . . . C86 C 0.1945(17) 0.2382(10) 0.5538(3) 0.028(3) 1.0000 Uiso D U . . . . . C96 C 0.2125(19) 0.3257(11) 0.5438(3) 0.028(3) 1.0000 Uiso D U . . . . . C106 C 0.350(2) 0.3853(9) 0.5559(3) 0.028(3) 1.0000 Uiso D U . . . . . C116 C 0.4693(17) 0.3588(9) 0.5760(3) 0.028(2) 1.0000 Uiso D U . . . . . C126 C 0.4449(15) 0.2666(7) 0.5853(2) 0.027(2) 1.0000 Uiso D U . . . . . C136 C 0.7161(14) 0.2580(8) 0.6169(2) 0.028(2) 1.0000 Uiso D U . . . . . C146 C 0.6916(14) 0.2922(9) 0.6442(2) 0.028(2) 1.0000 Uiso D U . . . . . C156 C 0.8542(18) 0.3393(9) 0.6538(2) 0.027(2) 1.0000 Uiso D U . . . . . C166 C 1.0192(17) 0.3516(9) 0.6380(3) 0.028(3) 1.0000 Uiso D U . . . . . C176 C 1.0211(17) 0.3157(9) 0.6128(3) 0.028(3) 1.0000 Uiso D U . . . . . C186 C 0.8732(18) 0.2707(9) 0.6022(2) 0.027(2) 1.0000 Uiso D U . . . . . C196 C 0.5185(16) 0.2822(16) 0.6585(2) 0.030(2) 1.0000 Uiso D U . . . . . C206 C 0.384(2) 0.3021(18) 0.7019(4) 0.031(3) 1.0000 Uiso D U . . . . . N17 N -0.1205(16) 0.2011(7) 0.7475(2) 0.0260(19) 1.0000 Uiso D U . . . . . O17 O 0.0500(18) 0.1584(11) 0.7003(3) 0.031(3) 1.0000 Uiso D U . . . . . O27 O -0.1298(16) 0.0988(11) 0.6683(3) 0.031(3) 1.0000 Uiso D U . . . . . C17 C -0.0096(15) 0.1642(7) 0.7679(2) 0.026(2) 1.0000 Uiso D U . . . . . C27 C -0.0298(17) 0.0810(9) 0.7821(3) 0.026(2) 1.0000 Uiso D U . . . . . C37 C 0.0933(19) 0.0656(9) 0.8028(3) 0.026(3) 1.0000 Uiso D U . . . . . C47 C 0.2328(18) 0.1311(10) 0.8092(3) 0.027(3) 1.0000 Uiso D U . . . . . C57 C 0.2535(17) 0.2132(9) 0.7951(3) 0.027(2) 1.0000 Uiso D U . . . . . C67 C 0.1364(15) 0.2324(7) 0.7748(2) 0.026(2) 1.0000 Uiso D U . . . . . C77 C 0.1099(15) 0.3113(7) 0.7568(2) 0.025(2) 1.0000 Uiso D U . . . . . C87 C 0.1896(17) 0.3986(9) 0.7533(3) 0.026(2) 1.0000 Uiso D U . . . . . C97 C 0.1277(19) 0.4610(9) 0.7353(3) 0.027(3) 1.0000 Uiso D U . . . . . C107 C -0.0265(19) 0.4379(9) 0.7181(3) 0.027(3) 1.0000 Uiso D U . . . . . C117 C -0.1200(17) 0.3508(9) 0.7202(3) 0.026(2) 1.0000 Uiso D U . . . . . C127 C -0.0435(15) 0.2895(7) 0.7402(2) 0.026(2) 1.0000 Uiso D U . . . . . C137 C -0.2719(14) 0.1486(8) 0.7351(2) 0.026(2) 1.0000 Uiso D U . . . . . C147 C -0.2700(14) 0.1192(9) 0.7091(2) 0.027(2) 1.0000 Uiso D U . . . . . C157 C -0.4337(18) 0.0761(9) 0.6996(2) 0.027(2) 1.0000 Uiso D U . . . . . C167 C -0.5863(17) 0.0665(9) 0.7156(3) 0.026(3) 1.0000 Uiso D U . . . . . C177 C -0.5927(17) 0.0946(9) 0.7408(3) 0.026(3) 1.0000 Uiso D U . . . . . C187 C -0.4341(18) 0.1372(9) 0.7513(2) 0.026(2) 1.0000 Uiso D U . . . . . C197 C -0.0896(17) 0.1298(16) 0.6931(2) 0.030(2) 1.0000 Uiso D U . . . . . C207 C 0.033(3) 0.1098(18) 0.6501(4) 0.033(3) 1.0000 Uiso D U . . . . . N18 N 0.3703(16) 0.2732(7) 0.8604(2) 0.0226(19) 1.0000 Uiso D U . . . . . O18 O 0.5680(17) 0.3309(11) 0.9038(3) 0.030(3) 1.0000 Uiso D U . . . . . O28 O 0.4080(15) 0.3920(11) 0.9373(3) 0.029(3) 1.0000 Uiso D U . . . . . C18 C 0.4873(14) 0.3106(7) 0.8413(2) 0.022(2) 1.0000 Uiso D U . . . . . C28 C 0.4707(16) 0.3951(9) 0.8277(3) 0.022(2) 1.0000 Uiso D U . . . . . C38 C 0.5978(19) 0.4126(9) 0.8078(3) 0.023(3) 1.0000 Uiso D U . . . . . C48 C 0.7391(17) 0.3464(10) 0.8012(2) 0.024(3) 1.0000 Uiso D U . . . . . C58 C 0.7576(17) 0.2627(9) 0.8148(3) 0.023(2) 1.0000 Uiso D U . . . . . C68 C 0.6242(15) 0.2446(7) 0.8359(2) 0.022(2) 1.0000 Uiso D U . . . . . C78 C 0.6050(15) 0.1683(7) 0.8549(2) 0.022(2) 1.0000 Uiso D U . . . . . C88 C 0.7078(16) 0.0829(9) 0.8597(3) 0.023(2) 1.0000 Uiso D U . . . . . C98 C 0.6352(18) 0.0238(8) 0.8799(3) 0.024(3) 1.0000 Uiso D U . . . . . C108 C 0.4777(18) 0.0487(9) 0.8938(3) 0.024(3) 1.0000 Uiso D U . . . . . C118 C 0.3829(16) 0.1308(9) 0.8888(3) 0.023(2) 1.0000 Uiso D U . . . . . C128 C 0.4449(14) 0.1893(7) 0.8697(2) 0.023(2) 1.0000 Uiso D U . . . . . C138 C 0.2125(14) 0.3210(8) 0.8726(2) 0.024(2) 1.0000 Uiso D U . . . . . C148 C 0.2393(14) 0.3668(8) 0.8968(2) 0.025(2) 1.0000 Uiso D U . . . . . C158 C 0.0893(18) 0.4213(9) 0.9076(2) 0.025(2) 1.0000 Uiso D U . . . . . C168 C -0.0848(18) 0.4294(9) 0.8943(3) 0.024(3) 1.0000 Uiso D U . . . . . C178 C -0.0993(17) 0.3810(9) 0.8695(3) 0.024(3) 1.0000 Uiso D U . . . . . C188 C 0.0503(18) 0.3280(9) 0.8594(2) 0.024(2) 1.0000 Uiso D U . . . . . C198 C 0.4164(15) 0.3638(15) 0.9122(3) 0.027(2) 1.0000 Uiso D U . . . . . C208 C 0.572(2) 0.3910(17) 0.9529(4) 0.029(3) 1.0000 Uiso D U . . . . . H1111 H -0.1199 0.8408 -0.1062 0.0298 1.0000 Uiso R . . . . . . H1011 H 0.0333 0.9812 -0.1128 0.0299 1.0000 Uiso R . . . . . . H911 H 0.2684 0.9998 -0.1442 0.0300 1.0000 Uiso R . . . . . . H811 H 0.3614 0.8772 -0.1710 0.0302 1.0000 Uiso R . . . . . . H511 H 0.3808 0.6967 -0.1972 0.0313 1.0000 Uiso R . . . . . . H411 H 0.3119 0.5478 -0.2155 0.0316 1.0000 Uiso R . . . . . . H311 H 0.0719 0.4558 -0.1987 0.0316 1.0000 Uiso R . . . . . . H211 H -0.1154 0.5071 -0.1636 0.0311 1.0000 Uiso R . . . . . . H1511 H -0.3954 0.6126 -0.0649 0.0294 1.0000 Uiso R . . . . . . H1611 H -0.6464 0.5527 -0.0874 0.0298 1.0000 Uiso R . . . . . . H1711 H -0.6414 0.5542 -0.1341 0.0303 1.0000 Uiso R . . . . . . H1811 H -0.3806 0.6134 -0.1574 0.0300 1.0000 Uiso R . . . . . . H2011 H -0.0220 0.7940 -0.0266 0.0309 1.0000 Uiso R . . . . . . H2012 H 0.1170 0.8068 -0.0517 0.0309 1.0000 Uiso R . . . . . . H2013 H 0.1142 0.7083 -0.0356 0.0309 1.0000 Uiso R . . . . . . H221 H 0.1892 0.4326 -0.0362 0.0326 1.0000 Uiso R . . . . . . H321 H 0.0207 0.5722 -0.0439 0.0330 1.0000 Uiso R . . . . . . H421 H -0.2432 0.6107 -0.0184 0.0332 1.0000 Uiso R . . . . . . H521 H -0.3524 0.5088 0.0148 0.0330 1.0000 Uiso R . . . . . . H821 H -0.3934 0.3591 0.0547 0.0337 1.0000 Uiso R . . . . . . H921 H -0.3598 0.2156 0.0766 0.0354 1.0000 Uiso R . . . . . . H1021 H -0.1405 0.1039 0.0659 0.0350 1.0000 Uiso R . . . . . . H1121 H 0.0774 0.1378 0.0312 0.0339 1.0000 Uiso R . . . . . . H1521 H 0.3635 0.1264 -0.0600 0.0313 1.0000 Uiso R . . . . . . H1621 H 0.6410 0.1146 -0.0382 0.0306 1.0000 Uiso R . . . . . . H1721 H 0.6796 0.1879 0.0035 0.0311 1.0000 Uiso R . . . . . . H1821 H 0.4202 0.2730 0.0213 0.0314 1.0000 Uiso R . . . . . . H2021 H -0.0846 0.1608 -0.1067 0.0352 1.0000 Uiso R . . . . . . H2022 H -0.1642 0.2494 -0.0899 0.0352 1.0000 Uiso R . . . . . . H2023 H -0.2117 0.1428 -0.0806 0.0352 1.0000 Uiso R . . . . . . H231 H 0.6417 0.2294 0.1537 0.0310 1.0000 Uiso R . . . . . . H331 H 0.4912 0.0812 0.1532 0.0319 1.0000 Uiso R . . . . . . H431 H 0.2490 0.0496 0.1234 0.0324 1.0000 Uiso R . . . . . . H531 H 0.1435 0.1643 0.0943 0.0322 1.0000 Uiso R . . . . . . H831 H 0.0916 0.3321 0.0633 0.0332 1.0000 Uiso R . . . . . . H931 H 0.1459 0.4766 0.0413 0.0343 1.0000 Uiso R . . . . . . H1031 H 0.3902 0.5737 0.0525 0.0336 1.0000 Uiso R . . . . . . H1131 H 0.5977 0.5350 0.0876 0.0322 1.0000 Uiso R . . . . . . H1531 H 0.8670 0.4739 0.1889 0.0282 1.0000 Uiso R . . . . . . H1631 H 1.1234 0.5258 0.1668 0.0285 1.0000 Uiso R . . . . . . H1731 H 1.1320 0.5088 0.1190 0.0288 1.0000 Uiso R . . . . . . H1831 H 0.8819 0.4404 0.0964 0.0294 1.0000 Uiso R . . . . . . H2031 H 0.4885 0.2863 0.2282 0.0298 1.0000 Uiso R . . . . . . H2032 H 0.3582 0.3722 0.2179 0.0298 1.0000 Uiso R . . . . . . H2033 H 0.3602 0.2730 0.2022 0.0298 1.0000 Uiso R . . . . . . H1141 H -0.1379 0.3544 0.2220 0.0312 1.0000 Uiso R . . . . . . H1041 H 0.0263 0.5030 0.2260 0.0320 1.0000 Uiso R . . . . . . H941 H 0.2693 0.5215 0.2572 0.0323 1.0000 Uiso R . . . . . . H841 H 0.3532 0.3915 0.2844 0.0320 1.0000 Uiso R . . . . . . H541 H 0.3782 0.2248 0.3148 0.0313 1.0000 Uiso R . . . . . . H441 H 0.3307 0.0770 0.3327 0.0319 1.0000 Uiso R . . . . . . H341 H 0.0983 -0.0264 0.3157 0.0316 1.0000 Uiso R . . . . . . H241 H -0.0958 0.0228 0.2801 0.0321 1.0000 Uiso R . . . . . . H1541 H -0.3558 0.1046 0.1820 0.0343 1.0000 Uiso R . . . . . . H1641 H -0.6301 0.0566 0.2059 0.0337 1.0000 Uiso R . . . . . . H1741 H -0.6521 0.0756 0.2512 0.0336 1.0000 Uiso R . . . . . . H1841 H -0.3967 0.1421 0.2741 0.0330 1.0000 Uiso R . . . . . . H2041 H 0.0160 0.2885 0.1451 0.0386 1.0000 Uiso R . . . . . . H2042 H 0.1329 0.3056 0.1720 0.0386 1.0000 Uiso R . . . . . . H2043 H 0.1485 0.2057 0.1568 0.0386 1.0000 Uiso R . . . . . . H251 H 0.0967 0.2658 0.4682 0.0301 1.0000 Uiso R . . . . . . H351 H -0.0669 0.4091 0.4732 0.0304 1.0000 Uiso R . . . . . . H451 H -0.3016 0.4258 0.5055 0.0306 1.0000 Uiso R . . . . . . H551 H -0.3896 0.2981 0.5322 0.0307 1.0000 Uiso R . . . . . . H851 H -0.4133 0.1239 0.5582 0.0307 1.0000 Uiso R . . . . . . H951 H -0.3621 -0.0178 0.5775 0.0308 1.0000 Uiso R . . . . . . H1051 H -0.1095 -0.1188 0.5614 0.0308 1.0000 Uiso R . . . . . . H1151 H 0.0821 -0.0663 0.5261 0.0303 1.0000 Uiso R . . . . . . H1551 H 0.3566 0.0371 0.4262 0.0309 1.0000 Uiso R . . . . . . H1651 H 0.6179 -0.0205 0.4515 0.0310 1.0000 Uiso R . . . . . . H1751 H 0.6127 -0.0186 0.4962 0.0312 1.0000 Uiso R . . . . . . H1851 H 0.3425 0.0407 0.5181 0.0316 1.0000 Uiso R . . . . . . H2051 H -0.0021 0.2190 0.3883 0.0334 1.0000 Uiso R . . . . . . H2052 H -0.1379 0.2331 0.4137 0.0334 1.0000 Uiso R . . . . . . H2053 H -0.1412 0.1348 0.3975 0.0334 1.0000 Uiso R . . . . . . H261 H 0.6063 0.0772 0.6405 0.0345 1.0000 Uiso R . . . . . . H361 H 0.4341 -0.0655 0.6408 0.0364 1.0000 Uiso R . . . . . . H461 H 0.1960 -0.0926 0.6104 0.0366 1.0000 Uiso R . . . . . . H561 H 0.1165 0.0196 0.5793 0.0357 1.0000 Uiso R . . . . . . H861 H 0.1004 0.1968 0.5467 0.0341 1.0000 Uiso R . . . . . . H961 H 0.1368 0.3474 0.5294 0.0341 1.0000 Uiso R . . . . . . H1061 H 0.3648 0.4481 0.5491 0.0341 1.0000 Uiso R . . . . . . H1161 H 0.5630 0.4003 0.5831 0.0332 1.0000 Uiso R . . . . . . H1561 H 0.8517 0.3649 0.6714 0.0326 1.0000 Uiso R . . . . . . H1661 H 1.1268 0.3843 0.6449 0.0326 1.0000 Uiso R . . . . . . H1761 H 1.1337 0.3224 0.6024 0.0326 1.0000 Uiso R . . . . . . H1861 H 0.8803 0.2462 0.5846 0.0326 1.0000 Uiso R . . . . . . H2061 H 0.4173 0.3220 0.7201 0.0376 1.0000 Uiso R . . . . . . H2062 H 0.3386 0.2360 0.7022 0.0376 1.0000 Uiso R . . . . . . H2063 H 0.2834 0.3436 0.6950 0.0376 1.0000 Uiso R . . . . . . H271 H -0.1252 0.0357 0.7777 0.0296 1.0000 Uiso R . . . . . . H371 H 0.0818 0.0090 0.8131 0.0295 1.0000 Uiso R . . . . . . H471 H 0.3159 0.1184 0.8237 0.0299 1.0000 Uiso R . . . . . . H571 H 0.3505 0.2572 0.7998 0.0302 1.0000 Uiso R . . . . . . H871 H 0.2968 0.4150 0.7638 0.0312 1.0000 Uiso R . . . . . . H971 H 0.1917 0.5203 0.7332 0.0317 1.0000 Uiso R . . . . . . H1071 H -0.0642 0.4821 0.7047 0.0318 1.0000 Uiso R . . . . . . H1171 H -0.2277 0.3346 0.7097 0.0312 1.0000 Uiso R . . . . . . H1571 H -0.4371 0.0523 0.6819 0.0311 1.0000 Uiso R . . . . . . H1671 H -0.6968 0.0377 0.7083 0.0310 1.0000 Uiso R . . . . . . H1771 H -0.7052 0.0871 0.7512 0.0310 1.0000 Uiso R . . . . . . H1871 H -0.4353 0.1603 0.7691 0.0305 1.0000 Uiso R . . . . . . H2071 H -0.0012 0.0867 0.6323 0.0373 1.0000 Uiso R . . . . . . H2072 H 0.1407 0.0726 0.6568 0.0373 1.0000 Uiso R . . . . . . H2073 H 0.0694 0.1772 0.6490 0.0373 1.0000 Uiso R . . . . . . H281 H 0.3727 0.4395 0.8318 0.0258 1.0000 Uiso R . . . . . . H381 H 0.5878 0.4698 0.7977 0.0258 1.0000 Uiso R . . . . . . H481 H 0.8240 0.3597 0.7869 0.0264 1.0000 Uiso R . . . . . . H581 H 0.8559 0.2186 0.8107 0.0259 1.0000 Uiso R . . . . . . H881 H 0.8170 0.0659 0.8495 0.0264 1.0000 Uiso R . . . . . . H981 H 0.6969 -0.0347 0.8839 0.0277 1.0000 Uiso R . . . . . . H1081 H 0.4321 0.0076 0.9075 0.0279 1.0000 Uiso R . . . . . . H1181 H 0.2739 0.1473 0.8991 0.0271 1.0000 Uiso R . . . . . . H1581 H 0.1054 0.4520 0.9243 0.0289 1.0000 Uiso R . . . . . . H1681 H -0.1870 0.4660 0.9013 0.0279 1.0000 Uiso R . . . . . . H1781 H -0.2133 0.3860 0.8595 0.0278 1.0000 Uiso R . . . . . . H1881 H 0.0373 0.2968 0.8427 0.0278 1.0000 Uiso R . . . . . . H2081 H 0.5405 0.4141 0.9708 0.0330 1.0000 Uiso R . . . . . . H2082 H 0.6223 0.3260 0.9541 0.0330 1.0000 Uiso R . . . . . . H2083 H 0.6674 0.4328 0.9448 0.0330 1.0000 Uiso R . . . . . . _refine_ls_extinction_method None #_oxford_refine_ls_scale 1.469(7) #loop_ # _oxford_twin_element_scale_factors # 0.891(5) # 0.109(5) 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 N11 . C121 . 1.474(10) yes N11 . C11 . 1.404(10) yes N11 . C131 . 1.359(11) yes O11 . C191 . 1.156(11) yes O21 . C191 . 1.365(12) yes O21 . C201 . 1.457(13) yes C121 . C111 . 1.289(12) yes C121 . C71 . 1.400(10) yes C111 . C101 . 1.311(12) yes C111 . H1111 . 0.950 no C101 . C91 . 1.365(12) yes C101 . H1011 . 0.950 no C91 . C81 . 1.337(12) yes C91 . H911 . 0.950 no C81 . C71 . 1.447(12) yes C81 . H811 . 0.950 no C71 . C61 . 1.467(11) yes C61 . C51 . 1.341(12) yes C61 . C11 . 1.442(10) yes C51 . C41 . 1.356(12) yes C51 . H511 . 0.950 no C41 . C31 . 1.382(12) yes C41 . H411 . 0.950 no C31 . C21 . 1.368(12) yes C31 . H311 . 0.950 no C21 . C11 . 1.375(12) yes C21 . H211 . 0.950 no C131 . C141 . 1.402(11) yes C131 . C181 . 1.452(12) yes C141 . C151 . 1.368(12) yes C141 . C191 . 1.458(11) yes C151 . C161 . 1.329(12) yes C151 . H1511 . 0.950 no C161 . C171 . 1.390(12) yes C161 . H1611 . 0.950 no C171 . C181 . 1.380(12) yes C171 . H1711 . 0.950 no C181 . H1811 . 0.950 no C201 . H2011 . 0.980 no C201 . H2012 . 0.980 no C201 . H2013 . 0.980 no N12 . C12 . 1.377(10) yes N12 . C122 . 1.432(10) yes N12 . C132 . 1.363(11) yes O12 . C192 . 1.243(11) yes O22 . C192 . 1.255(12) yes O22 . C202 . 1.462(13) yes C12 . C22 . 1.370(12) yes C12 . C62 . 1.420(10) yes C22 . C32 . 1.365(12) yes C22 . H221 . 0.950 no C32 . C42 . 1.383(12) yes C32 . H321 . 0.950 no C42 . C52 . 1.373(12) yes C42 . H421 . 0.950 no C52 . C62 . 1.368(12) yes C52 . H521 . 0.950 no C62 . C72 . 1.354(11) yes C72 . C82 . 1.460(12) yes C72 . C122 . 1.415(10) yes C82 . C92 . 1.386(12) yes C82 . H821 . 0.950 no C92 . C102 . 1.336(12) yes C92 . H921 . 0.950 no C102 . C112 . 1.391(12) yes C102 . H1021 . 0.950 no C112 . C122 . 1.352(12) yes C112 . H1121 . 0.950 no C132 . C142 . 1.342(11) yes C132 . C182 . 1.410(12) yes C142 . C152 . 1.364(12) yes C142 . C192 . 1.531(11) yes C152 . C162 . 1.314(12) yes C152 . H1521 . 0.950 no C162 . C172 . 1.380(12) yes C162 . H1621 . 0.950 no C172 . C182 . 1.400(12) yes C172 . H1721 . 0.950 no C182 . H1821 . 0.950 no C202 . H2021 . 0.980 no C202 . H2022 . 0.980 no C202 . H2023 . 0.980 no N13 . C13 . 1.401(10) yes N13 . C123 . 1.355(11) yes N13 . C133 . 1.414(11) yes O13 . C193 . 1.223(11) yes O23 . C193 . 1.352(12) yes O23 . C203 . 1.437(13) yes C13 . C23 . 1.376(12) yes C13 . C63 . 1.429(10) yes C23 . C33 . 1.376(12) yes C23 . H231 . 0.950 no C33 . C43 . 1.380(12) yes C33 . H331 . 0.950 no C43 . C53 . 1.353(12) yes C43 . H431 . 0.950 no C53 . C63 . 1.352(12) yes C53 . H531 . 0.950 no C63 . C73 . 1.402(11) yes C73 . C83 . 1.373(12) yes C73 . C123 . 1.447(10) yes C83 . C93 . 1.399(12) yes C83 . H831 . 0.950 no C93 . C103 . 1.344(12) yes C93 . H931 . 0.950 no C103 . C113 . 1.394(12) yes C103 . H1031 . 0.950 no C113 . C123 . 1.383(12) yes C113 . H1131 . 0.950 no C133 . C143 . 1.367(11) yes C133 . C183 . 1.440(12) yes C143 . C153 . 1.419(12) yes C143 . C193 . 1.426(11) yes C153 . C163 . 1.300(12) yes C153 . H1531 . 0.950 no C163 . C173 . 1.453(12) yes C163 . H1631 . 0.950 no C173 . C183 . 1.351(12) yes C173 . H1731 . 0.950 no C183 . H1831 . 0.950 no C203 . H2031 . 0.980 no C203 . H2032 . 0.980 no C203 . H2033 . 0.980 no N14 . C124 . 1.357(10) yes N14 . C14 . 1.375(11) yes N14 . C134 . 1.483(11) yes O14 . C194 . 1.229(12) yes O24 . C194 . 1.317(12) yes O24 . C204 . 1.408(13) yes C124 . C114 . 1.465(12) yes C124 . C74 . 1.416(11) yes C114 . C104 . 1.432(12) yes C114 . H1141 . 0.950 no C104 . C94 . 1.404(12) yes C104 . H1041 . 0.950 no C94 . C84 . 1.398(12) yes C94 . H941 . 0.950 no C84 . C74 . 1.317(12) yes C84 . H841 . 0.950 no C74 . C64 . 1.407(11) yes C64 . C54 . 1.448(12) yes C64 . C14 . 1.355(10) yes C54 . C44 . 1.362(12) yes C54 . H541 . 0.950 no C44 . C34 . 1.388(12) yes C44 . H441 . 0.950 no C34 . C24 . 1.383(12) yes C34 . H341 . 0.950 no C24 . C14 . 1.382(12) yes C24 . H241 . 0.950 no C134 . C144 . 1.350(11) yes C134 . C184 . 1.346(12) yes C144 . C154 . 1.405(12) yes C144 . C194 . 1.503(11) yes C154 . C164 . 1.411(12) yes C154 . H1541 . 0.950 no C164 . C174 . 1.348(12) yes C164 . H1641 . 0.950 no C174 . C184 . 1.373(12) yes C174 . H1741 . 0.950 no C184 . H1841 . 0.950 no C204 . H2041 . 0.980 no C204 . H2042 . 0.980 no C204 . H2043 . 0.980 no N15 . C15 . 1.391(10) yes N15 . C125 . 1.425(10) yes N15 . C135 . 1.426(11) yes O15 . C195 . 1.189(11) yes O25 . C195 . 1.293(12) yes O25 . C205 . 1.453(13) yes C15 . C25 . 1.382(12) yes C15 . C65 . 1.360(10) yes C25 . C35 . 1.373(12) yes C25 . H251 . 0.950 no C35 . C45 . 1.389(12) yes C35 . H351 . 0.950 no C45 . C55 . 1.362(12) yes C45 . H451 . 0.950 no C55 . C65 . 1.434(12) yes C55 . H551 . 0.950 no C65 . C75 . 1.460(11) yes C75 . C85 . 1.393(12) yes C75 . C125 . 1.351(10) yes C85 . C95 . 1.289(12) yes C85 . H851 . 0.950 no C95 . C105 . 1.453(12) yes C95 . H951 . 0.950 no C105 . C115 . 1.375(12) yes C105 . H1051 . 0.950 no C115 . C125 . 1.350(12) yes C115 . H1151 . 0.950 no C135 . C145 . 1.409(11) yes C135 . C185 . 1.308(12) yes C145 . C155 . 1.336(12) yes C145 . C195 . 1.558(11) yes C155 . C165 . 1.427(12) yes C155 . H1551 . 0.950 no C165 . C175 . 1.293(12) yes C165 . H1651 . 0.950 no C175 . C185 . 1.402(12) yes C175 . H1751 . 0.950 no C185 . H1851 . 0.950 no C205 . H2051 . 0.980 no C205 . H2052 . 0.980 no C205 . H2053 . 0.980 no N16 . C16 . 1.402(10) yes N16 . C126 . 1.318(11) yes N16 . C136 . 1.469(11) yes O16 . C196 . 1.134(12) yes O26 . C196 . 1.397(12) yes O26 . C206 . 1.441(13) yes C16 . C26 . 1.374(12) yes C16 . C66 . 1.388(11) yes C26 . C36 . 1.381(12) yes C26 . H261 . 0.950 no C36 . C46 . 1.371(12) yes C36 . H361 . 0.950 no C46 . C56 . 1.340(12) yes C46 . H461 . 0.950 no C56 . C66 . 1.404(12) yes C56 . H561 . 0.950 no C66 . C76 . 1.516(11) yes C76 . C86 . 1.355(12) yes C76 . C126 . 1.399(10) yes C86 . C96 . 1.331(12) yes C86 . H861 . 0.950 no C96 . C106 . 1.418(12) yes C96 . H961 . 0.950 no C106 . C116 . 1.364(12) yes C106 . H1061 . 0.950 no C116 . C126 . 1.384(12) yes C116 . H1161 . 0.950 no C136 . C146 . 1.458(11) yes C136 . C186 . 1.338(12) yes C146 . C156 . 1.408(12) yes C146 . C196 . 1.418(11) yes C156 . C166 . 1.414(12) yes C156 . H1561 . 0.950 no C166 . C176 . 1.361(12) yes C166 . H1661 . 0.950 no C176 . C186 . 1.330(12) yes C176 . H1761 . 0.950 no C186 . H1861 . 0.950 no C206 . H2061 . 0.980 no C206 . H2062 . 0.980 no C206 . H2063 . 0.980 no N17 . C17 . 1.387(11) yes N17 . C127 . 1.401(10) yes N17 . C137 . 1.437(11) yes O17 . C197 . 1.121(12) yes O27 . C197 . 1.350(12) yes O27 . C207 . 1.472(13) yes C17 . C27 . 1.375(12) yes C17 . C67 . 1.446(10) yes C27 . C37 . 1.372(12) yes C27 . H271 . 0.950 no C37 . C47 . 1.382(12) yes C37 . H371 . 0.950 no C47 . C57 . 1.358(12) yes C47 . H471 . 0.950 no C57 . C67 . 1.341(12) yes C57 . H571 . 0.950 no C67 . C77 . 1.441(11) yes C77 . C87 . 1.358(12) yes C77 . C127 . 1.397(11) yes C87 . C97 . 1.334(12) yes C87 . H871 . 0.950 no C97 . C107 . 1.425(12) yes C97 . H971 . 0.950 no C107 . C117 . 1.392(12) yes C107 . H1071 . 0.950 no C117 . C127 . 1.429(12) yes C117 . H1171 . 0.950 no C137 . C147 . 1.372(11) yes C137 . C187 . 1.405(12) yes C147 . C157 . 1.385(12) yes C147 . C197 . 1.504(11) yes C157 . C167 . 1.344(12) yes C157 . H1571 . 0.950 no C167 . C177 . 1.326(12) yes C167 . H1671 . 0.950 no C177 . C187 . 1.372(12) yes C177 . H1771 . 0.950 no C187 . H1871 . 0.950 no C207 . H2071 . 0.980 no C207 . H2072 . 0.980 no C207 . H2073 . 0.980 no N18 . C18 . 1.368(10) yes N18 . C128 . 1.371(10) yes N18 . C138 . 1.432(11) yes O18 . C198 . 1.233(11) yes O28 . C198 . 1.321(12) yes O28 . C208 . 1.395(13) yes C18 . C28 . 1.372(12) yes C18 . C68 . 1.361(10) yes C28 . C38 . 1.362(12) yes C28 . H281 . 0.950 no C38 . C48 . 1.399(12) yes C38 . H381 . 0.950 no C48 . C58 . 1.365(12) yes C48 . H481 . 0.950 no C58 . C68 . 1.437(12) yes C58 . H581 . 0.950 no C68 . C78 . 1.438(11) yes C78 . C88 . 1.419(12) yes C78 . C128 . 1.377(10) yes C88 . C98 . 1.405(12) yes C88 . H881 . 0.950 no C98 . C108 . 1.351(12) yes C98 . H981 . 0.950 no C108 . C118 . 1.354(12) yes C108 . H1081 . 0.950 no C118 . C128 . 1.334(12) yes C118 . H1181 . 0.950 no C138 . C148 . 1.384(11) yes C138 . C188 . 1.324(12) yes C148 . C158 . 1.409(12) yes C148 . C198 . 1.469(11) yes C158 . C168 . 1.402(12) yes C158 . H1581 . 0.950 no C168 . C178 . 1.418(12) yes C168 . H1681 . 0.950 no C178 . C188 . 1.382(12) yes C178 . H1781 . 0.950 no C188 . H1881 . 0.950 no C208 . H2081 . 0.980 no C208 . H2082 . 0.980 no C208 . H2083 . 0.980 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 C121 . N11 . C11 . 109.2(4) yes C121 . N11 . C131 . 123.7(5) yes C11 . N11 . C131 . 127.0(5) yes C191 . O21 . C201 . 118.2(6) yes N11 . C121 . C111 . 130.8(5) yes N11 . C121 . C71 . 105.0(4) yes C111 . C121 . C71 . 123.6(5) yes C121 . C111 . C101 . 117.3(6) yes C121 . C111 . H1111 . 121.1 no C101 . C111 . H1111 . 121.6 no C111 . C101 . C91 . 124.1(6) yes C111 . C101 . H1011 . 118.9 no C91 . C101 . H1011 . 117.0 no C101 . C91 . C81 . 122.2(6) yes C101 . C91 . H911 . 121.7 no C81 . C91 . H911 . 116.1 no C91 . C81 . C71 . 114.3(5) yes C91 . C81 . H811 . 123.2 no C71 . C81 . H811 . 122.5 no C81 . C71 . C121 . 118.6(5) yes C81 . C71 . C61 . 129.3(5) yes C121 . C71 . C61 . 111.7(4) yes C71 . C61 . C51 . 136.3(5) yes C71 . C61 . C11 . 104.5(4) yes C51 . C61 . C11 . 119.1(5) yes C61 . C51 . C41 . 120.1(6) yes C61 . C51 . H511 . 120.4 no C41 . C51 . H511 . 119.4 no C51 . C41 . C31 . 121.1(6) yes C51 . C41 . H411 . 122.4 no C31 . C41 . H411 . 116.5 no C41 . C31 . C21 . 121.5(5) yes C41 . C31 . H311 . 120.3 no C21 . C31 . H311 . 118.3 no C31 . C21 . C11 . 117.6(5) yes C31 . C21 . H211 . 121.0 no C11 . C21 . H211 . 121.4 no C61 . C11 . N11 . 109.5(4) yes C61 . C11 . C21 . 120.6(4) yes N11 . C11 . C21 . 129.8(5) yes N11 . C131 . C141 . 126.9(5) yes N11 . C131 . C181 . 116.2(5) yes C141 . C131 . C181 . 116.9(5) yes C131 . C141 . C151 . 119.8(5) yes C131 . C141 . C191 . 115.2(5) yes C151 . C141 . C191 . 124.6(5) yes C141 . C151 . C161 . 124.4(6) yes C141 . C151 . H1511 . 118.1 no C161 . C151 . H1511 . 117.5 no C151 . C161 . C171 . 118.1(6) yes C151 . C161 . H1611 . 121.2 no C171 . C161 . H1611 . 120.6 no C161 . C171 . C181 . 121.6(6) yes C161 . C171 . H1711 . 119.5 no C181 . C171 . H1711 . 118.9 no C131 . C181 . C171 . 119.2(5) yes C131 . C181 . H1811 . 120.1 no C171 . C181 . H1811 . 120.7 no C141 . C191 . O21 . 108.3(5) yes C141 . C191 . O11 . 133.8(6) yes O21 . C191 . O11 . 117.7(6) yes O21 . C201 . H2011 . 109.0 no O21 . C201 . H2012 . 110.3 no H2011 . C201 . H2012 . 109.5 no O21 . C201 . H2013 . 109.1 no H2011 . C201 . H2013 . 109.5 no H2012 . C201 . H2013 . 109.5 no C12 . N12 . C122 . 107.0(4) yes C12 . N12 . C132 . 128.5(5) yes C122 . N12 . C132 . 122.6(5) yes C192 . O22 . C202 . 116.9(6) yes N12 . C12 . C22 . 128.7(5) yes N12 . C12 . C62 . 109.5(4) yes C22 . C12 . C62 . 121.8(5) yes C12 . C22 . C32 . 117.9(5) yes C12 . C22 . H221 . 121.3 no C32 . C22 . H221 . 120.8 no C22 . C32 . C42 . 121.1(6) yes C22 . C32 . H321 . 119.7 no C42 . C32 . H321 . 119.2 no C32 . C42 . C52 . 121.3(6) yes C32 . C42 . H421 . 119.6 no C52 . C42 . H421 . 119.2 no C42 . C52 . C62 . 119.1(5) yes C42 . C52 . H521 . 120.6 no C62 . C52 . H521 . 120.2 no C12 . C62 . C52 . 118.8(5) yes C12 . C62 . C72 . 107.0(4) yes C52 . C62 . C72 . 134.2(5) yes C62 . C72 . C82 . 136.7(5) yes C62 . C72 . C122 . 110.1(4) yes C82 . C72 . C122 . 113.2(5) yes C72 . C82 . C92 . 118.3(5) yes C72 . C82 . H821 . 121.0 no C92 . C82 . H821 . 120.7 no C82 . C92 . C102 . 125.8(6) yes C82 . C92 . H921 . 117.2 no C102 . C92 . H921 . 117.0 no C92 . C102 . C112 . 117.3(6) yes C92 . C102 . H1021 . 121.4 no C112 . C102 . H1021 . 121.2 no C102 . C112 . C122 . 119.8(5) yes C102 . C112 . H1121 . 120.2 no C122 . C112 . H1121 . 119.9 no N12 . C122 . C72 . 106.0(4) yes N12 . C122 . C112 . 128.4(5) yes C72 . C122 . C112 . 125.5(5) yes N12 . C132 . C142 . 127.7(5) yes N12 . C132 . C182 . 116.7(5) yes C142 . C132 . C182 . 115.5(5) yes C132 . C142 . C152 . 122.6(5) yes C132 . C142 . C192 . 118.2(5) yes C152 . C142 . C192 . 119.2(5) yes C142 . C152 . C162 . 122.0(5) yes C142 . C152 . H1521 . 118.9 no C162 . C152 . H1521 . 119.1 no C152 . C162 . C172 . 120.5(6) yes C152 . C162 . H1621 . 119.6 no C172 . C162 . H1621 . 119.9 no C162 . C172 . C182 . 117.0(6) yes C162 . C172 . H1721 . 121.4 no C182 . C172 . H1721 . 121.6 no C132 . C182 . C172 . 122.4(5) yes C132 . C182 . H1821 . 118.9 no C172 . C182 . H1821 . 118.7 no C142 . C192 . O22 . 114.2(5) yes C142 . C192 . O12 . 121.9(5) yes O22 . C192 . O12 . 123.9(5) yes O22 . C202 . H2021 . 109.1 no O22 . C202 . H2022 . 108.6 no H2021 . C202 . H2022 . 109.5 no O22 . C202 . H2023 . 110.7 no H2021 . C202 . H2023 . 109.5 no H2022 . C202 . H2023 . 109.5 no C13 . N13 . C123 . 108.1(4) yes C13 . N13 . C133 . 124.3(5) yes C123 . N13 . C133 . 127.6(5) yes C193 . O23 . C203 . 118.3(6) yes N13 . C13 . C23 . 129.9(5) yes N13 . C13 . C63 . 108.9(4) yes C23 . C13 . C63 . 120.7(5) yes C13 . C23 . C33 . 117.4(5) yes C13 . C23 . H231 . 121.2 no C33 . C23 . H231 . 121.3 no C23 . C33 . C43 . 121.3(6) yes C23 . C33 . H331 . 119.2 no C43 . C33 . H331 . 119.5 no C33 . C43 . C53 . 121.2(6) yes C33 . C43 . H431 . 119.2 no C53 . C43 . H431 . 119.5 no C43 . C53 . C63 . 119.8(5) yes C43 . C53 . H531 . 120.0 no C63 . C53 . H531 . 120.2 no C13 . C63 . C53 . 119.4(5) yes C13 . C63 . C73 . 106.7(4) yes C53 . C63 . C73 . 133.7(5) yes C63 . C73 . C83 . 135.9(5) yes C63 . C73 . C123 . 106.7(4) yes C83 . C73 . C123 . 117.2(5) yes C73 . C83 . C93 . 119.6(5) yes C73 . C83 . H831 . 120.7 no C93 . C83 . H831 . 119.7 no C83 . C93 . C103 . 122.0(6) yes C83 . C93 . H931 . 119.4 no C103 . C93 . H931 . 118.5 no C93 . C103 . C113 . 121.9(6) yes C93 . C103 . H1031 . 119.5 no C113 . C103 . H1031 . 118.6 no C103 . C113 . C123 . 116.7(5) yes C103 . C113 . H1131 . 122.0 no C123 . C113 . H1131 . 121.3 no C73 . C123 . C113 . 122.7(5) yes C73 . C123 . N13 . 109.4(4) yes C113 . C123 . N13 . 127.9(5) yes N13 . C133 . C143 . 119.7(5) yes N13 . C133 . C183 . 118.6(5) yes C143 . C133 . C183 . 121.7(5) yes C133 . C143 . C153 . 116.8(5) yes C133 . C143 . C193 . 122.9(5) yes C153 . C143 . C193 . 120.2(5) yes C143 . C153 . C163 . 124.9(6) yes C143 . C153 . H1531 . 117.9 no C163 . C153 . H1531 . 117.2 no C153 . C163 . C173 . 117.3(6) yes C153 . C163 . H1631 . 121.6 no C173 . C163 . H1631 . 121.1 no C163 . C173 . C183 . 121.9(6) yes C163 . C173 . H1731 . 119.2 no C183 . C173 . H1731 . 118.8 no C133 . C183 . C173 . 117.4(5) yes C133 . C183 . H1831 . 121.0 no C173 . C183 . H1831 . 121.6 no C143 . C193 . O23 . 114.2(5) yes C143 . C193 . O13 . 128.5(5) yes O23 . C193 . O13 . 117.3(5) yes O23 . C203 . H2031 . 109.8 no O23 . C203 . H2032 . 108.8 no H2031 . C203 . H2032 . 109.5 no O23 . C203 . H2033 . 109.7 no H2031 . C203 . H2033 . 109.5 no H2032 . C203 . H2033 . 109.5 no C124 . N14 . C14 . 108.1(4) yes C124 . N14 . C134 . 126.2(5) yes C14 . N14 . C134 . 125.6(5) yes C194 . O24 . C204 . 115.0(7) yes N14 . C124 . C114 . 128.4(5) yes N14 . C124 . C74 . 110.3(4) yes C114 . C124 . C74 . 120.8(4) yes C124 . C114 . C104 . 116.5(5) yes C124 . C114 . H1141 . 121.6 no C104 . C114 . H1141 . 121.9 no C114 . C104 . C94 . 120.6(5) yes C114 . C104 . H1041 . 118.8 no C94 . C104 . H1041 . 120.6 no C104 . C94 . C84 . 118.3(5) yes C104 . C94 . H941 . 117.9 no C84 . C94 . H941 . 123.8 no C94 . C84 . C74 . 125.4(6) yes C94 . C84 . H841 . 116.7 no C74 . C84 . H841 . 117.9 no C124 . C74 . C84 . 118.4(5) yes C124 . C74 . C64 . 102.7(4) yes C84 . C74 . C64 . 138.5(5) yes C74 . C64 . C54 . 130.2(5) yes C74 . C64 . C14 . 111.2(5) yes C54 . C64 . C14 . 118.7(4) yes C64 . C54 . C44 . 117.9(5) yes C64 . C54 . H541 . 120.2 no C44 . C54 . H541 . 121.9 no C54 . C44 . C34 . 121.6(6) yes C54 . C44 . H441 . 116.2 no C34 . C44 . H441 . 122.1 no C44 . C34 . C24 . 120.9(6) yes C44 . C34 . H341 . 118.6 no C24 . C34 . H341 . 120.6 no C34 . C24 . C14 . 117.5(6) yes C34 . C24 . H241 . 121.0 no C14 . C24 . H241 . 121.5 no C24 . C14 . N14 . 129.1(5) yes C24 . C14 . C64 . 123.4(5) yes N14 . C14 . C64 . 107.4(4) yes N14 . C134 . C144 . 117.4(5) yes N14 . C134 . C184 . 119.9(5) yes C144 . C134 . C184 . 122.5(5) yes C134 . C144 . C154 . 119.0(5) yes C134 . C144 . C194 . 126.2(5) yes C154 . C144 . C194 . 114.7(5) yes C144 . C154 . C164 . 117.0(5) yes C144 . C154 . H1541 . 121.3 no C164 . C154 . H1541 . 121.7 no C154 . C164 . C174 . 122.3(6) yes C154 . C164 . H1641 . 118.6 no C174 . C164 . H1641 . 119.1 no C164 . C174 . C184 . 118.4(6) yes C164 . C174 . H1741 . 120.4 no C184 . C174 . H1741 . 121.1 no C174 . C184 . C134 . 120.7(5) yes C174 . C184 . H1841 . 119.4 no C134 . C184 . H1841 . 119.9 no C144 . C194 . O24 . 113.3(5) yes C144 . C194 . O14 . 119.9(5) yes O24 . C194 . O14 . 126.8(6) yes O24 . C204 . H2041 . 109.8 no O24 . C204 . H2042 . 109.7 no H2041 . C204 . H2042 . 109.5 no O24 . C204 . H2043 . 108.9 no H2041 . C204 . H2043 . 109.5 no H2042 . C204 . H2043 . 109.5 no C15 . N15 . C125 . 109.0(4) yes C15 . N15 . C135 . 127.9(5) yes C125 . N15 . C135 . 123.1(5) yes C195 . O25 . C205 . 114.6(6) yes N15 . C15 . C25 . 129.2(5) yes N15 . C15 . C65 . 107.5(4) yes C25 . C15 . C65 . 122.7(5) yes C15 . C25 . C35 . 117.7(5) yes C15 . C25 . H251 . 121.0 no C35 . C25 . H251 . 121.2 no C25 . C35 . C45 . 121.1(6) yes C25 . C35 . H351 . 119.2 no C45 . C35 . H351 . 119.6 no C35 . C45 . C55 . 121.3(6) yes C35 . C45 . H451 . 119.2 no C55 . C45 . H451 . 119.5 no C45 . C55 . C65 . 118.0(5) yes C45 . C55 . H551 . 121.0 no C65 . C55 . H551 . 121.0 no C55 . C65 . C15 . 119.1(5) yes C55 . C65 . C75 . 132.1(5) yes C15 . C65 . C75 . 108.4(4) yes C65 . C75 . C85 . 131.3(5) yes C65 . C75 . C125 . 107.3(4) yes C85 . C75 . C125 . 121.4(5) yes C75 . C85 . C95 . 119.9(5) yes C75 . C85 . H851 . 119.9 no C95 . C85 . H851 . 120.2 no C85 . C95 . C105 . 119.7(6) yes C85 . C95 . H951 . 120.0 no C105 . C95 . H951 . 120.3 no C95 . C105 . C115 . 119.5(6) yes C95 . C105 . H1051 . 120.1 no C115 . C105 . H1051 . 120.4 no C105 . C115 . C125 . 118.6(5) yes C105 . C115 . H1151 . 120.7 no C125 . C115 . H1151 . 120.7 no N15 . C125 . C75 . 107.8(4) yes N15 . C125 . C115 . 131.3(5) yes C75 . C125 . C115 . 120.9(5) yes N15 . C135 . C145 . 122.1(5) yes N15 . C135 . C185 . 119.5(5) yes C145 . C135 . C185 . 118.3(5) yes C135 . C145 . C155 . 120.8(5) yes C135 . C145 . C195 . 120.8(5) yes C155 . C145 . C195 . 118.2(5) yes C145 . C155 . C165 . 117.7(5) yes C145 . C155 . H1551 . 121.0 no C165 . C155 . H1551 . 121.2 no C155 . C165 . C175 . 122.3(6) yes C155 . C165 . H1651 . 118.8 no C175 . C165 . H1651 . 118.9 no C165 . C175 . C185 . 118.0(6) yes C165 . C175 . H1751 . 121.0 no C185 . C175 . H1751 . 121.0 no C175 . C185 . C135 . 123.0(6) yes C175 . C185 . H1851 . 118.5 no C135 . C185 . H1851 . 118.4 no C145 . C195 . O25 . 108.1(5) yes C145 . C195 . O15 . 120.4(5) yes O25 . C195 . O15 . 131.4(5) yes O25 . C205 . H2051 . 109.3 no O25 . C205 . H2052 . 108.8 no H2051 . C205 . H2052 . 109.5 no O25 . C205 . H2053 . 110.3 no H2051 . C205 . H2053 . 109.5 no H2052 . C205 . H2053 . 109.5 no C16 . N16 . C126 . 109.6(4) yes C16 . N16 . C136 . 123.9(5) yes C126 . N16 . C136 . 126.3(5) yes C196 . O26 . C206 . 114.7(7) yes N16 . C16 . C26 . 130.0(5) yes N16 . C16 . C66 . 108.5(4) yes C26 . C16 . C66 . 121.5(5) yes C16 . C26 . C36 . 117.3(5) yes C16 . C26 . H261 . 121.2 no C36 . C26 . H261 . 121.4 no C26 . C36 . C46 . 121.5(6) yes C26 . C36 . H361 . 119.1 no C46 . C36 . H361 . 119.4 no C36 . C46 . C56 . 121.5(6) yes C36 . C46 . H461 . 119.1 no C56 . C46 . H461 . 119.3 no C46 . C56 . C66 . 118.9(5) yes C46 . C56 . H561 . 120.5 no C66 . C56 . H561 . 120.7 no C56 . C66 . C16 . 119.2(5) yes C56 . C66 . C76 . 134.7(5) yes C16 . C66 . C76 . 106.1(4) yes C66 . C76 . C86 . 135.2(5) yes C66 . C76 . C126 . 103.3(4) yes C86 . C76 . C126 . 121.3(5) yes C76 . C86 . C96 . 121.4(5) yes C76 . C86 . H861 . 119.5 no C96 . C86 . H861 . 119.2 no C86 . C96 . C106 . 116.5(6) yes C86 . C96 . H961 . 122.0 no C106 . C96 . H961 . 121.4 no C96 . C106 . C116 . 125.2(6) yes C96 . C106 . H1061 . 117.8 no C116 . C106 . H1061 . 117.0 no C106 . C116 . C126 . 115.3(5) yes C106 . C116 . H1161 . 122.6 no C126 . C116 . H1161 . 122.1 no C76 . C126 . C116 . 120.2(5) yes C76 . C126 . N16 . 112.2(4) yes C116 . C126 . N16 . 127.6(5) yes N16 . C136 . C146 . 114.9(5) yes N16 . C136 . C186 . 119.6(5) yes C146 . C136 . C186 . 124.6(5) yes C136 . C146 . C156 . 112.6(5) yes C136 . C146 . C196 . 122.7(5) yes C156 . C146 . C196 . 124.6(5) yes C146 . C156 . C166 . 122.0(5) yes C146 . C156 . H1561 . 118.9 no C166 . C156 . H1561 . 119.1 no C156 . C166 . C176 . 118.8(6) yes C156 . C166 . H1661 . 120.6 no C176 . C166 . H1661 . 120.6 no C166 . C176 . C186 . 122.8(6) yes C166 . C176 . H1761 . 118.5 no C186 . C176 . H1761 . 118.6 no C136 . C186 . C176 . 119.2(5) yes C136 . C186 . H1861 . 120.4 no C176 . C186 . H1861 . 120.4 no C146 . C196 . O26 . 108.7(5) yes C146 . C196 . O16 . 130.5(5) yes O26 . C196 . O16 . 120.8(5) yes O26 . C206 . H2061 . 109.5 no O26 . C206 . H2062 . 109.1 no H2061 . C206 . H2062 . 109.5 no O26 . C206 . H2063 . 109.8 no H2061 . C206 . H2063 . 109.5 no H2062 . C206 . H2063 . 109.5 no C17 . N17 . C127 . 107.8(4) yes C17 . N17 . C137 . 123.1(5) yes C127 . N17 . C137 . 128.8(5) yes C197 . O27 . C207 . 112.0(7) yes N17 . C17 . C27 . 129.9(5) yes N17 . C17 . C67 . 109.3(4) yes C27 . C17 . C67 . 120.6(5) yes C17 . C27 . C37 . 117.5(5) yes C17 . C27 . H271 . 121.3 no C37 . C27 . H271 . 121.2 no C27 . C37 . C47 . 121.4(6) yes C27 . C37 . H371 . 119.4 no C47 . C37 . H371 . 119.2 no C37 . C47 . C57 . 121.2(6) yes C37 . C47 . H471 . 119.5 no C57 . C47 . H471 . 119.4 no C47 . C57 . C67 . 120.0(5) yes C47 . C57 . H571 . 120.0 no C67 . C57 . H571 . 120.0 no C17 . C67 . C57 . 119.2(5) yes C17 . C67 . C77 . 105.3(4) yes C57 . C67 . C77 . 135.4(5) yes C67 . C77 . C87 . 135.9(5) yes C67 . C77 . C127 . 107.8(4) yes C87 . C77 . C127 . 116.1(5) yes C77 . C87 . C97 . 122.9(5) yes C77 . C87 . H871 . 118.4 no C97 . C87 . H871 . 118.6 no C87 . C97 . C107 . 120.8(6) yes C87 . C97 . H971 . 119.4 no C107 . C97 . H971 . 119.7 no C97 . C107 . C117 . 120.9(6) yes C97 . C107 . H1071 . 119.5 no C117 . C107 . H1071 . 119.6 no C107 . C117 . C127 . 113.8(5) yes C107 . C117 . H1171 . 123.0 no C127 . C117 . H1171 . 123.2 no C117 . C127 . N17 . 124.8(5) yes C117 . C127 . C77 . 125.4(5) yes N17 . C127 . C77 . 109.7(4) yes N17 . C137 . C147 . 124.1(5) yes N17 . C137 . C187 . 114.3(5) yes C147 . C137 . C187 . 121.3(5) yes C137 . C147 . C157 . 116.9(5) yes C137 . C147 . C197 . 118.9(5) yes C157 . C147 . C197 . 124.2(5) yes C147 . C157 . C167 . 120.2(5) yes C147 . C157 . H1571 . 119.8 no C167 . C157 . H1571 . 120.0 no C157 . C167 . C177 . 124.3(6) yes C157 . C167 . H1671 . 117.7 no C177 . C167 . H1671 . 117.9 no C167 . C177 . C187 . 118.0(6) yes C167 . C177 . H1771 . 120.9 no C187 . C177 . H1771 . 121.1 no C137 . C187 . C177 . 119.3(5) yes C137 . C187 . H1871 . 120.5 no C177 . C187 . H1871 . 120.2 no C147 . C197 . O27 . 106.2(5) yes C147 . C197 . O17 . 127.1(5) yes O27 . C197 . O17 . 126.6(6) yes O27 . C207 . H2071 . 109.6 no O27 . C207 . H2072 . 109.2 no H2071 . C207 . H2072 . 109.5 no O27 . C207 . H2073 . 109.6 no H2071 . C207 . H2073 . 109.5 no H2072 . C207 . H2073 . 109.5 no C18 . N18 . C128 . 109.7(4) yes C18 . N18 . C138 . 125.8(5) yes C128 . N18 . C138 . 123.6(5) yes C198 . O28 . C208 . 119.9(6) yes N18 . C18 . C28 . 128.9(5) yes N18 . C18 . C68 . 107.5(4) yes C28 . C18 . C68 . 123.5(5) yes C18 . C28 . C38 . 117.6(5) yes C18 . C28 . H281 . 121.4 no C38 . C28 . H281 . 121.0 no C28 . C38 . C48 . 121.2(6) yes C28 . C38 . H381 . 119.6 no C48 . C38 . H381 . 119.2 no C38 . C48 . C58 . 121.4(6) yes C38 . C48 . H481 . 119.5 no C58 . C48 . H481 . 119.1 no C48 . C58 . C68 . 117.3(5) yes C48 . C58 . H581 . 121.5 no C68 . C58 . H581 . 121.2 no C58 . C68 . C18 . 118.9(5) yes C58 . C68 . C78 . 132.9(5) yes C18 . C68 . C78 . 108.1(4) yes C68 . C78 . C88 . 133.8(5) yes C68 . C78 . C128 . 105.8(4) yes C88 . C78 . C128 . 120.4(5) yes C78 . C88 . C98 . 115.8(5) yes C78 . C88 . H881 . 122.2 no C98 . C88 . H881 . 122.0 no C88 . C98 . C108 . 121.0(6) yes C88 . C98 . H981 . 119.7 no C108 . C98 . H981 . 119.3 no C98 . C108 . C118 . 121.9(6) yes C98 . C108 . H1081 . 119.2 no C118 . C108 . H1081 . 118.9 no C108 . C118 . C128 . 119.7(5) yes C108 . C118 . H1181 . 120.2 no C128 . C118 . H1181 . 120.1 no C78 . C128 . N18 . 108.3(4) yes C78 . C128 . C118 . 121.3(5) yes N18 . C128 . C118 . 130.4(5) yes N18 . C138 . C148 . 118.9(5) yes N18 . C138 . C188 . 119.3(5) yes C148 . C138 . C188 . 121.5(5) yes C138 . C148 . C158 . 119.0(5) yes C138 . C148 . C198 . 124.4(5) yes C158 . C148 . C198 . 116.6(5) yes C148 . C158 . C168 . 120.9(5) yes C148 . C158 . H1581 . 119.6 no C168 . C158 . H1581 . 119.5 no C158 . C168 . C178 . 116.4(6) yes C158 . C168 . H1681 . 121.9 no C178 . C168 . H1681 . 121.8 no C168 . C178 . C188 . 121.4(6) yes C168 . C178 . H1781 . 119.4 no C188 . C178 . H1781 . 119.2 no C178 . C188 . C138 . 120.8(5) yes C178 . C188 . H1881 . 119.6 no C138 . C188 . H1881 . 119.5 no C148 . C198 . O28 . 117.2(5) yes C148 . C198 . O18 . 124.4(5) yes O28 . C198 . O18 . 118.2(6) yes O28 . C208 . H2081 . 109.2 no O28 . C208 . H2082 . 110.1 no H2081 . C208 . H2082 . 109.5 no O28 . C208 . H2083 . 109.1 no H2081 . C208 . H2083 . 109.5 no H2082 . C208 . H2083 . 109.5 no _chemical_name_common 'Methyl 2-(9H-carbazol-9-yl)benzoate' _exptl_crystal_recrystallization_method ; A mixture of carbazole, methyl 2-iodobenzoate, copper powder, potassium carbonate and nitrobenzene were heated at 175 degrees C for 48 h. After cooling, the resultant mixture was a red solid. A mixture of water/chloroform (1:1) was added to the solid, and the two layers separated. The aqueous layer was then extracted twice with chloroform, and the organic layers were combined and dried over MgSO4. The solvent was removed under reduced pressure, and the residue oil was purified by flash dry chromatography on silica using hexane/ethyl acetate (85:15) as the eluant. This resulted in the formation of colourless crystals. (5.30 g, 88%) ; #edit data_5_3GPa_II.cif _database_code_depnum_ccdc_archive 'CCDC 752560' #_oxford_structure_analysis_title 'mben09 in P2(1)2(1)2(1)' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 7.701(2) _cell_length_b 12.569(6) _cell_length_c 24.786(13) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2399.2(18) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,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 0.0000 0.0010 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0010 0.0010 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0030 0.0030 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C20 H15 N1 O2 # Dc = 1.67 Fooo = 1264.00 Mu = 1.08 M = 602.69 # Found Formula = C20 H15 N1 O2 # Dc = 1.67 FOOO = 1264.00 Mu = 1.08 M = 602.69 _chemical_formula_sum 'C20 H15 N1 O2' _chemical_formula_moiety 'C20 H15 N1 O2' _chemical_compound_source ? _chemical_formula_weight 301.34 _cell_measurement_reflns_used 1139 _cell_measurement_theta_min 2 _cell_measurement_theta_max 14 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.668 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.108 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.79 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device APEX-II _diffrn_measurement_device_type Area _diffrn_radiation_monochromator silicon _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.47620 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 293 _diffrn_ambient_pressure 5300000 _diffrn_reflns_number 9206 _reflns_number_total 1574 _diffrn_reflns_av_R_equivalents 0.145 # Number of reflections with Friedels Law is 1574 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1716 _diffrn_reflns_reduction_process ; Merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 ; _diffrn_reflns_theta_min 1.217 _diffrn_reflns_theta_max 15.328 _diffrn_measured_fraction_theta_max 0.790 _diffrn_reflns_theta_full 11.956 _diffrn_measured_fraction_theta_full 0.835 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 24 _reflns_limit_h_min 0 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 24 #_oxford_diffrn_Wilson_B_factor 1.31 #_oxford_diffrn_Wilson_scale 0.15 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.25 _refine_diff_density_max 0.29 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement #_oxford_reflns_threshold_expression_ref I>2.0\s(I) _refine_ls_number_reflns 1222 _refine_ls_number_restraints 462 _refine_ls_number_parameters 439 #_oxford_refine_ls_R_factor_ref 0.0510 _refine_ls_wR_factor_ref 0.0570 _refine_ls_goodness_of_fit_ref 1.0302 _refine_ls_shift/su_max 0.000158 # The values computed from all data #_oxford_reflns_number_all 1535 _refine_ls_R_factor_all 0.0735 _refine_ls_wR_factor_all 0.1079 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1222 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_gt 0.0570 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 12.9 -10.2 8.53 ; 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens N11 N 0.5617(6) 0.1817(4) 0.5902(2) 0.0265 1.0000 Uani . U . . . . . O11 O 0.5968(5) 0.1084(4) 0.75775(19) 0.0343 1.0000 Uani . U . . . . . O21 O 0.4263(5) 0.1539(4) 0.68850(18) 0.0349 1.0000 Uani D U . . . . . C11 C 0.4812(7) 0.1227(5) 0.5494(3) 0.0252 1.0000 Uani . U . . . . . C21 C 0.5279(8) 0.0282(5) 0.5267(3) 0.0258 1.0000 Uani . U . . . . . C31 C 0.4303(8) -0.0076(6) 0.4832(3) 0.0300 1.0000 Uani . U . . . . . C41 C 0.2924(8) 0.0525(5) 0.4619(3) 0.0300 1.0000 Uani . U . . . . . C51 C 0.2400(8) 0.1433(6) 0.4884(3) 0.0276 1.0000 Uani . U . . . . . C61 C 0.3349(7) 0.1795(5) 0.5320(3) 0.0240 1.0000 Uani . U . . . . . C71 C 0.3185(7) 0.2740(5) 0.5659(3) 0.0213 1.0000 Uani . U . . . . . C81 C 0.1969(8) 0.3534(5) 0.5689(3) 0.0280 1.0000 Uani . U . . . . . C91 C 0.2260(7) 0.4352(6) 0.6050(3) 0.0279 1.0000 Uani . U . . . . . C101 C 0.3755(7) 0.4376(5) 0.6360(3) 0.0235 1.0000 Uani . U . . . . . C111 C 0.4985(7) 0.3575(5) 0.6343(3) 0.0222 1.0000 Uani . U . . . . . C121 C 0.4657(7) 0.2734(5) 0.6001(3) 0.0226 1.0000 Uani . U . . . . . C131 C 0.7138(7) 0.1432(5) 0.6157(3) 0.0241 1.0000 Uani . U . . . . . C141 C 0.7170(7) 0.1089(5) 0.6700(3) 0.0218 1.0000 Uani . U . . . . . C151 C 0.8701(7) 0.0637(5) 0.6898(3) 0.0268 1.0000 Uani . U . . . . . C161 C 1.0169(8) 0.0534(5) 0.6577(3) 0.0289 1.0000 Uani . U . . . . . C171 C 1.0127(7) 0.0902(5) 0.6055(3) 0.0305 1.0000 Uani . U . . . . . C181 C 0.8626(7) 0.1330(6) 0.5840(3) 0.0300 1.0000 Uani . U . . . . . C191 C 0.5777(7) 0.1222(5) 0.7101(3) 0.0224 1.0000 Uani . U . . . . . C201 C 0.3026(8) 0.2077(6) 0.7243(3) 0.0354 1.0000 Uani D U . . . . . N12 N 0.0984(6) -0.2187(5) 0.6175(2) 0.0261 1.0000 Uani . . . . . . . O12 O -0.0365(5) -0.1537(3) 0.72355(17) 0.0278 1.0000 Uani . U . . . . . O22 O 0.1685(5) -0.1838(4) 0.78628(18) 0.0286 1.0000 Uani D U . . . . . C12 C -0.0059(7) -0.2991(5) 0.6399(3) 0.0234 1.0000 Uani . U . . . . . C22 C 0.0312(7) -0.3681(5) 0.6806(3) 0.0271 1.0000 Uani . U . . . . . C32 C -0.0986(8) -0.4363(5) 0.6965(3) 0.0279 1.0000 Uani . U . . . . . C42 C -0.2618(8) -0.4369(5) 0.6716(3) 0.0266 1.0000 Uani . U . . . . . C52 C -0.2931(7) -0.3713(5) 0.6280(3) 0.0258 1.0000 Uani . U . . . . . C62 C -0.1623(7) -0.3059(5) 0.6101(3) 0.0255 1.0000 Uani . U . . . . . C72 C -0.1460(7) -0.2316(5) 0.5660(3) 0.0220 1.0000 Uani . U . . . . . C82 C -0.2499(7) -0.2105(5) 0.5206(3) 0.0242 1.0000 Uani . U . . . . . C92 C -0.1954(8) -0.1369(5) 0.4845(3) 0.0311 1.0000 Uani . U . . . . . C102 C -0.0441(8) -0.0776(6) 0.4920(3) 0.0298 1.0000 Uani . U . . . . . C112 C 0.0619(7) -0.0985(5) 0.5370(3) 0.0248 1.0000 Uani . U . . . . . C122 C 0.0124(7) -0.1780(5) 0.5727(3) 0.0239 1.0000 Uani . U . . . . . C132 C 0.2527(7) -0.1794(5) 0.6418(3) 0.0229 1.0000 Uani . U . . . . . C142 C 0.2649(7) -0.1632(5) 0.6976(3) 0.0237 1.0000 Uani . U . . . . . C152 C 0.4245(7) -0.1339(5) 0.7199(3) 0.0243 1.0000 Uani . U . . . . . C162 C 0.5671(7) -0.1151(5) 0.6876(3) 0.0289 1.0000 Uani . U . . . . . C172 C 0.5500(7) -0.1244(5) 0.6326(3) 0.0295 1.0000 Uani . U . . . . . C182 C 0.3972(7) -0.1594(6) 0.6099(3) 0.0306 1.0000 Uani . U . . . . . C192 C 0.1141(7) -0.1669(5) 0.7352(3) 0.0246 1.0000 Uani . U . . . . . C202 C 0.0396(8) -0.1712(5) 0.8283(3) 0.0273 1.0000 Uani D U . . . . . H211 H 0.6234 -0.0116 0.5401 0.0310 1.0000 Uiso R . . . . . . H311 H 0.4575 -0.0745 0.4675 0.0359 1.0000 Uiso R . . . . . . H411 H 0.2362 0.0307 0.4296 0.0358 1.0000 Uiso R . . . . . . H511 H 0.1393 0.1806 0.4768 0.0331 1.0000 Uiso R . . . . . . H811 H 0.0961 0.3523 0.5468 0.0335 1.0000 Uiso R . . . . . . H911 H 0.1425 0.4904 0.6087 0.0334 1.0000 Uiso R . . . . . . H1011 H 0.3944 0.4966 0.6592 0.0281 1.0000 Uiso R . . . . . . H1111 H 0.6007 0.3602 0.6558 0.0268 1.0000 Uiso R . . . . . . H1511 H 0.8738 0.0394 0.7260 0.0321 1.0000 Uiso R . . . . . . H1611 H 1.1191 0.0213 0.6716 0.0348 1.0000 Uiso R . . . . . . H1711 H 1.1144 0.0862 0.5840 0.0370 1.0000 Uiso R . . . . . . H1811 H 0.8607 0.1556 0.5474 0.0358 1.0000 Uiso R . . . . . . H2011 H 0.189(2) 0.174(3) 0.7211(15) 0.0499(16) 1.0000 Uiso D . . . . . . H2012 H 0.343(4) 0.203(3) 0.7617(5) 0.0499(16) 1.0000 Uiso D . . . . . . H2013 H 0.292(5) 0.2824(12) 0.7133(14) 0.0502(16) 1.0000 Uiso D . . . . . . H221 H 0.1422 -0.3691 0.6974 0.0324 1.0000 Uiso R . . . . . . H321 H -0.0768 -0.4845 0.7253 0.0336 1.0000 Uiso R . . . . . . H421 H -0.3509 -0.4823 0.6847 0.0319 1.0000 Uiso R . . . . . . H521 H -0.4032 -0.3713 0.6108 0.0310 1.0000 Uiso R . . . . . . H821 H -0.3564 -0.2472 0.5152 0.0289 1.0000 Uiso R . . . . . . H921 H -0.2629 -0.1250 0.4530 0.0374 1.0000 Uiso R . . . . . . H1021 H -0.0130 -0.0238 0.4669 0.0356 1.0000 Uiso R . . . . . . H1121 H 0.1655 -0.0590 0.5428 0.0295 1.0000 Uiso R . . . . . . H1521 H 0.4350 -0.1269 0.7580 0.0288 1.0000 Uiso R . . . . . . H1621 H 0.6754 -0.0959 0.7031 0.0348 1.0000 Uiso R . . . . . . H1721 H 0.6451 -0.1065 0.6099 0.0357 1.0000 Uiso R . . . . . . H1821 H 0.3905 -0.1699 0.5720 0.0369 1.0000 Uiso R . . . . . . H2021 H 0.093(3) -0.140(3) 0.8605(8) 0.0500(16) 1.0000 Uiso D . . . . . . H2022 H -0.010(4) -0.2408(13) 0.8372(15) 0.0499(16) 1.0000 Uiso D . . . . . . H2023 H -0.053(3) -0.124(3) 0.8159(11) 0.0499(16) 1.0000 Uiso D . . . . . . 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 0.0238(19) 0.029(2) 0.027(3) -0.0019(15) -0.0028(17) 0.0006(12) O11 0.037(2) 0.044(3) 0.022(2) 0.001(2) -0.0010(18) 0.002(2) O21 0.0325(19) 0.048(3) 0.024(3) 0.0045(19) 0.0023(16) 0.017(2) C11 0.024(3) 0.024(3) 0.027(4) 0.0005(19) 0.001(2) -0.0055(19) C21 0.025(3) 0.026(3) 0.026(4) 0.001(2) 0.011(2) -0.006(2) C31 0.034(3) 0.023(4) 0.032(4) -0.003(2) 0.007(2) -0.011(2) C41 0.041(3) 0.028(4) 0.021(4) 0.001(2) 0.003(2) -0.012(3) C51 0.030(3) 0.034(4) 0.019(4) -0.001(2) 0.001(2) -0.009(2) C61 0.024(3) 0.023(3) 0.024(4) 0.0013(19) -0.002(2) -0.008(2) C71 0.031(2) 0.021(3) 0.012(4) 0.0074(19) -0.001(2) -0.004(2) C81 0.032(3) 0.035(4) 0.017(4) 0.009(2) -0.004(2) 0.005(2) C91 0.026(3) 0.037(4) 0.022(5) 0.003(2) 0.009(2) 0.006(3) C101 0.028(3) 0.020(3) 0.022(4) 0.002(2) 0.007(2) 0.000(2) C111 0.027(3) 0.025(3) 0.014(4) 0.004(2) -0.001(2) 0.002(2) C121 0.025(2) 0.024(3) 0.019(4) 0.0037(19) 0.000(2) -0.002(2) C131 0.026(2) 0.022(4) 0.024(2) 0.000(2) -0.0030(16) 0.001(2) C141 0.024(2) 0.019(4) 0.022(2) -0.004(2) -0.0067(17) -0.003(2) C151 0.028(2) 0.019(4) 0.033(4) 0.002(3) -0.0064(19) 0.002(2) C161 0.028(3) 0.018(4) 0.040(4) -0.001(3) -0.003(2) -0.005(3) C171 0.034(3) 0.017(4) 0.040(4) -0.001(3) 0.004(2) 0.012(3) C181 0.030(2) 0.030(4) 0.030(4) 0.000(3) 0.0017(19) 0.004(3) C191 0.026(2) 0.017(4) 0.024(2) 0.001(2) -0.0039(16) -0.005(2) C201 0.035(3) 0.044(5) 0.027(5) 0.003(3) 0.011(3) 0.008(3) N12 0.026(2) 0.031(4) 0.022(4) 0.003(2) 0.003(2) -0.005(3) O12 0.0225(15) 0.030(3) 0.031(3) -0.0011(18) -0.0008(15) 0.0022(19) O22 0.028(2) 0.035(3) 0.023(2) 0.0043(19) 0.0047(13) 0.004(2) C12 0.021(2) 0.026(3) 0.023(4) -0.001(2) 0.003(2) 0.0032(19) C22 0.022(2) 0.029(4) 0.031(4) 0.002(2) -0.002(2) 0.009(2) C32 0.041(3) 0.018(4) 0.025(4) 0.003(2) -0.002(2) 0.003(2) C42 0.033(2) 0.012(4) 0.034(5) -0.001(2) 0.003(2) -0.001(2) C52 0.021(2) 0.027(4) 0.030(4) -0.001(2) -0.001(2) 0.002(2) C62 0.023(2) 0.025(4) 0.029(4) 0.001(2) -0.0008(19) 0.003(2) C72 0.024(2) 0.023(4) 0.020(3) -0.0048(19) 0.0008(19) 0.0030(19) C82 0.030(3) 0.021(4) 0.021(4) -0.008(2) -0.004(2) 0.004(2) C92 0.029(3) 0.033(5) 0.031(4) 0.008(2) -0.004(2) 0.014(2) C102 0.035(3) 0.026(4) 0.028(4) 0.005(2) 0.003(2) 0.010(2) C112 0.025(3) 0.026(4) 0.023(4) -0.002(2) 0.0068(19) 0.003(2) C122 0.027(2) 0.032(3) 0.013(3) -0.003(2) 0.000(2) -0.002(2) C132 0.019(2) 0.024(3) 0.026(2) -0.005(2) -0.0027(17) 0.005(2) C142 0.0205(17) 0.028(4) 0.023(2) 0.002(2) -0.0043(16) 0.002(2) C152 0.024(2) 0.023(4) 0.026(3) -0.001(2) -0.0060(17) 0.001(2) C162 0.025(2) 0.025(4) 0.037(3) -0.004(3) 0.000(2) 0.000(3) C172 0.018(2) 0.037(4) 0.034(3) 0.007(3) 0.002(2) 0.008(3) C182 0.027(2) 0.034(3) 0.031(3) -0.005(3) 0.0042(19) 0.000(3) C192 0.0239(16) 0.024(4) 0.026(2) 0.003(3) -0.0015(16) 0.002(3) C202 0.034(3) 0.021(4) 0.027(3) -0.007(3) 0.006(2) 0.010(3) _refine_ls_extinction_method None #_oxford_refine_ls_scale 3.042(11) 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 N11 . C11 . 1.399(8) yes N11 . C121 . 1.392(8) yes N11 . C131 . 1.416(7) yes O11 . C191 . 1.203(7) yes O21 . C191 . 1.344(7) yes O21 . C201 . 1.467(8) yes C11 . C21 . 1.362(9) yes C11 . C61 . 1.402(8) yes C21 . C31 . 1.389(9) yes C21 . H211 . 0.950 no C31 . C41 . 1.407(10) yes C31 . H311 . 0.950 no C41 . C51 . 1.377(10) yes C41 . H411 . 0.950 no C51 . C61 . 1.382(9) yes C51 . H511 . 0.950 no C61 . C71 . 1.461(9) yes C71 . C81 . 1.371(8) yes C71 . C121 . 1.415(8) yes C81 . C91 . 1.382(10) yes C81 . H811 . 0.950 no C91 . C101 . 1.384(8) yes C91 . H911 . 0.950 no C101 . C111 . 1.384(8) yes C101 . H1011 . 0.950 no C111 . C121 . 1.378(9) yes C111 . H1111 . 0.950 no C131 . C141 . 1.413(9) yes C131 . C181 . 1.395(9) yes C141 . C151 . 1.398(8) yes C141 . C191 . 1.473(9) yes C151 . C161 . 1.388(9) yes C151 . H1511 . 0.950 no C161 . C171 . 1.373(10) yes C161 . H1611 . 0.950 no C171 . C181 . 1.383(9) yes C171 . H1711 . 0.950 no C181 . H1811 . 0.950 no C201 . H2011 . 0.980(8) no C201 . H2012 . 0.980(8) no C201 . H2013 . 0.980(8) no N12 . C12 . 1.405(8) yes N12 . C122 . 1.390(8) yes N12 . C132 . 1.421(8) yes O12 . C192 . 1.207(7) yes O22 . C192 . 1.351(7) yes O22 . C202 . 1.448(7) yes C12 . C22 . 1.361(9) yes C12 . C62 . 1.415(8) yes C22 . C32 . 1.374(9) yes C22 . H221 . 0.950 no C32 . C42 . 1.401(9) yes C32 . H321 . 0.950 no C42 . C52 . 1.380(9) yes C42 . H421 . 0.950 no C52 . C62 . 1.374(8) yes C52 . H521 . 0.950 no C62 . C72 . 1.444(9) yes C72 . C82 . 1.408(9) yes C72 . C122 . 1.403(8) yes C82 . C92 . 1.352(10) yes C82 . H821 . 0.950 no C92 . C102 . 1.395(10) yes C92 . H921 . 0.950 no C102 . C112 . 1.407(9) yes C102 . H1021 . 0.950 no C112 . C122 . 1.389(9) yes C112 . H1121 . 0.950 no C132 . C142 . 1.400(9) yes C132 . C182 . 1.388(9) yes C142 . C152 . 1.398(8) yes C142 . C192 . 1.490(8) yes C152 . C162 . 1.379(8) yes C152 . H1521 . 0.950 no C162 . C172 . 1.375(9) yes C162 . H1621 . 0.950 no C172 . C182 . 1.376(9) yes C172 . H1721 . 0.950 no C182 . H1821 . 0.950 no C202 . H2021 . 0.980(8) no C202 . H2022 . 0.981(8) no C202 . H2023 . 0.980(8) 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 C11 . N11 . C121 . 109.3(5) yes C11 . N11 . C131 . 120.5(6) yes C121 . N11 . C131 . 130.1(5) yes C191 . O21 . C201 . 117.3(5) yes N11 . C11 . C21 . 130.0(6) yes N11 . C11 . C61 . 108.0(6) yes C21 . C11 . C61 . 121.9(6) yes C11 . C21 . C31 . 117.4(6) yes C11 . C21 . H211 . 121.3 no C31 . C21 . H211 . 121.3 no C21 . C31 . C41 . 121.8(6) yes C21 . C31 . H311 . 119.1 no C41 . C31 . H311 . 119.1 no C31 . C41 . C51 . 119.1(7) yes C31 . C41 . H411 . 120.4 no C51 . C41 . H411 . 120.4 no C41 . C51 . C61 . 119.4(6) yes C41 . C51 . H511 . 120.3 no C61 . C51 . H511 . 120.3 no C11 . C61 . C51 . 119.9(7) yes C11 . C61 . C71 . 107.8(6) yes C51 . C61 . C71 . 132.3(6) yes C61 . C71 . C81 . 132.9(6) yes C61 . C71 . C121 . 105.8(5) yes C81 . C71 . C121 . 121.3(6) yes C71 . C81 . C91 . 117.7(5) yes C71 . C81 . H811 . 121.2 no C91 . C81 . H811 . 121.1 no C81 . C91 . C101 . 120.7(6) yes C81 . C91 . H911 . 119.7 no C101 . C91 . H911 . 119.6 no C91 . C101 . C111 . 122.5(6) yes C91 . C101 . H1011 . 118.7 no C111 . C101 . H1011 . 118.8 no C101 . C111 . C121 . 116.8(5) yes C101 . C111 . H1111 . 121.6 no C121 . C111 . H1111 . 121.6 no C71 . C121 . N11 . 108.9(5) yes C71 . C121 . C111 . 120.8(5) yes N11 . C121 . C111 . 130.3(5) yes N11 . C131 . C141 . 122.9(5) yes N11 . C131 . C181 . 117.3(6) yes C141 . C131 . C181 . 119.6(5) yes C131 . C141 . C151 . 118.3(5) yes C131 . C141 . C191 . 126.6(5) yes C151 . C141 . C191 . 115.0(6) yes C141 . C151 . C161 . 121.5(7) yes C141 . C151 . H1511 . 119.2 no C161 . C151 . H1511 . 119.2 no C151 . C161 . C171 . 119.3(6) yes C151 . C161 . H1611 . 120.4 no C171 . C161 . H1611 . 120.3 no C161 . C171 . C181 . 121.0(6) yes C161 . C171 . H1711 . 119.5 no C181 . C171 . H1711 . 119.5 no C131 . C181 . C171 . 120.3(6) yes C131 . C181 . H1811 . 119.9 no C171 . C181 . H1811 . 119.9 no C141 . C191 . O21 . 113.4(5) yes C141 . C191 . O11 . 123.9(6) yes O21 . C191 . O11 . 122.7(6) yes O21 . C201 . H2011 . 109.3(14) no O21 . C201 . H2012 . 109.6(14) no H2011 . C201 . H2012 . 109.7(14) no O21 . C201 . H2013 . 109.0(14) no H2011 . C201 . H2013 . 109.0(14) no H2012 . C201 . H2013 . 110.1(14) no C12 . N12 . C122 . 107.9(5) yes C12 . N12 . C132 . 124.1(6) yes C122 . N12 . C132 . 127.5(6) yes C192 . O22 . C202 . 116.4(4) yes N12 . C12 . C22 . 129.1(5) yes N12 . C12 . C62 . 108.9(6) yes C22 . C12 . C62 . 121.8(6) yes C12 . C22 . C32 . 117.2(5) yes C12 . C22 . H221 . 121.4 no C32 . C22 . H221 . 121.4 no C22 . C32 . C42 . 122.0(6) yes C22 . C32 . H321 . 119.0 no C42 . C32 . H321 . 119.0 no C32 . C42 . C52 . 119.9(6) yes C32 . C42 . H421 . 120.1 no C52 . C42 . H421 . 120.0 no C42 . C52 . C62 . 118.8(5) yes C42 . C52 . H521 . 120.6 no C62 . C52 . H521 . 120.6 no C12 . C62 . C52 . 119.5(6) yes C12 . C62 . C72 . 106.3(5) yes C52 . C62 . C72 . 134.1(5) yes C62 . C72 . C82 . 132.7(5) yes C62 . C72 . C122 . 107.3(5) yes C82 . C72 . C122 . 119.9(6) yes C72 . C82 . C92 . 118.8(6) yes C72 . C82 . H821 . 120.7 no C92 . C82 . H821 . 120.6 no C82 . C92 . C102 . 122.5(6) yes C82 . C92 . H921 . 118.7 no C102 . C92 . H921 . 118.8 no C92 . C102 . C112 . 119.4(6) yes C92 . C102 . H1021 . 120.3 no C112 . C102 . H1021 . 120.3 no C102 . C112 . C122 . 118.7(6) yes C102 . C112 . H1121 . 120.6 no C122 . C112 . H1121 . 120.7 no C72 . C122 . N12 . 109.4(6) yes C72 . C122 . C112 . 120.6(6) yes N12 . C122 . C112 . 130.0(5) yes N12 . C132 . C142 . 121.7(5) yes N12 . C132 . C182 . 119.5(6) yes C142 . C132 . C182 . 118.8(5) yes C132 . C142 . C152 . 119.3(5) yes C132 . C142 . C192 . 124.1(5) yes C152 . C142 . C192 . 116.4(6) yes C142 . C152 . C162 . 121.0(6) yes C142 . C152 . H1521 . 119.5 no C162 . C152 . H1521 . 119.5 no C152 . C162 . C172 . 119.0(6) yes C152 . C162 . H1621 . 120.5 no C172 . C162 . H1621 . 120.5 no C162 . C172 . C182 . 120.9(6) yes C162 . C172 . H1721 . 119.5 no C182 . C172 . H1721 . 119.6 no C132 . C182 . C172 . 120.7(7) yes C132 . C182 . H1821 . 119.6 no C172 . C182 . H1821 . 119.7 no C142 . C192 . O22 . 110.5(5) yes C142 . C192 . O12 . 126.5(6) yes O22 . C192 . O12 . 122.9(5) yes O22 . C202 . H2021 . 109.9(14) no O22 . C202 . H2022 . 109.5(14) no H2021 . C202 . H2022 . 109.5(14) no O22 . C202 . H2023 . 110.0(14) no H2021 . C202 . H2023 . 108.8(14) no H2022 . C202 . H2023 . 109.1(14) no _chemical_name_common 'Methyl 2-(9H-carbazol-9-yl)benzoate' _exptl_crystal_recrystallization_method ; A mixture of carbazole, methyl 2-iodobenzoate, copper powder, potassium carbonate and nitrobenzene were heated at 175 degrees C for 48 h. After cooling, the resultant mixture was a red solid. A mixture of water/chloroform (1:1) was added to the solid, and the two layers separated. The aqueous layer was then extracted twice with chloroform, and the organic layers were combined and dried over MgSO4. The solvent was removed under reduced pressure, and the residue oil was purified by flash dry chromatography on silica using hexane/ethyl acetate (85:15) as the eluant. This resulted in the formation of colourless crystals. (5.30 g, 88%) ; #edit data_6_0GPa_II.cif _database_code_depnum_ccdc_archive 'CCDC 752561' #_oxford_structure_analysis_title 'benm06 in P2(1)2(1)2(1)' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 7.6475(7) _cell_length_b 12.451(3) _cell_length_c 24.651(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2347.3(6) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,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 0.0010 0.0010 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0020 0.0010 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0030 0.0030 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C20 H15 N1 O2 # Dc = 1.71 Fooo = 1264.00 Mu = 1.10 M = 602.69 # Found Formula = C20 H15 N1 O2 # Dc = 1.71 FOOO = 1264.00 Mu = 1.10 M = 602.69 _chemical_formula_sum 'C20 H15 N1 O2' _chemical_formula_moiety 'C20 H15 N1 O2' _chemical_compound_source ? _chemical_formula_weight 301.34 _cell_measurement_reflns_used 3040 _cell_measurement_theta_min 2 _cell_measurement_theta_max 16 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.705 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.110 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.80 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device APEX-II _diffrn_measurement_device_type Area _diffrn_radiation_monochromator silicon _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.47920 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 293 _diffrn_ambient_pressure 6000000 _diffrn_reflns_number 10237 _reflns_number_total 1216 _diffrn_reflns_av_R_equivalents 0.0779 # Number of reflections with Friedels Law is 1216 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1695 _diffrn_reflns_reduction_process ; Merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 ; _diffrn_reflns_theta_min 1.114 _diffrn_reflns_theta_max 15.519 _diffrn_measured_fraction_theta_max 0.614 _diffrn_reflns_theta_full 12.105 _diffrn_measured_fraction_theta_full 0.639 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 27 _reflns_limit_h_min 0 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 27 #_oxford_diffrn_Wilson_B_factor 0.00 #_oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.12 _refine_diff_density_max 0.11 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement #_oxford_reflns_threshold_expression_ref I>2.0\s(I) _refine_ls_number_reflns 1071 _refine_ls_number_restraints 462 _refine_ls_number_parameters 439 #_oxford_refine_ls_R_factor_ref 0.0277 _refine_ls_wR_factor_ref 0.0233 _refine_ls_goodness_of_fit_ref 1.0753 _refine_ls_shift/su_max 0.000297 # The values computed from all data #_oxford_reflns_number_all 1179 _refine_ls_R_factor_all 0.0359 _refine_ls_wR_factor_all 0.0277 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1071 _refine_ls_R_factor_gt 0.0277 _refine_ls_wR_factor_gt 0.0233 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 6.79 -7.24 3.33 ; 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens N11 N 0.5635(3) 0.1822(4) 0.58986(8) 0.0221 1.0000 Uani . U . . . . . O11 O 0.5988(2) 0.1107(3) 0.75757(7) 0.0316 1.0000 Uani . U . . . . . O21 O 0.4254(2) 0.1533(3) 0.68786(7) 0.0291 1.0000 Uani D U . . . . . C11 C 0.4828(4) 0.1231(5) 0.54891(10) 0.0223 1.0000 Uani . U . . . . . C21 C 0.5313(4) 0.0269(5) 0.52623(10) 0.0229 1.0000 Uani . U . . . . . C31 C 0.4338(4) -0.0100(4) 0.48248(10) 0.0262 1.0000 Uani . U . . . . . C41 C 0.2955(4) 0.0491(5) 0.46183(11) 0.0249 1.0000 Uani . U . . . . . C51 C 0.2413(4) 0.1408(5) 0.48716(10) 0.0227 1.0000 Uani . U . . . . . C61 C 0.3358(4) 0.1792(5) 0.53163(11) 0.0228 1.0000 Uani . U . . . . . C71 C 0.3194(4) 0.2729(5) 0.56561(10) 0.0214 1.0000 Uani . U . . . . . C81 C 0.1965(4) 0.3510(5) 0.57004(11) 0.0216 1.0000 Uani . U . . . . . C91 C 0.2250(4) 0.4364(5) 0.60426(10) 0.0226 1.0000 Uani . U . . . . . C101 C 0.3759(4) 0.4411(4) 0.63600(10) 0.0244 1.0000 Uani . U . . . . . C111 C 0.4996(4) 0.3616(5) 0.63375(11) 0.0250 1.0000 Uani . U . . . . . C121 C 0.4673(4) 0.2741(4) 0.59971(10) 0.0198 1.0000 Uani . U . . . . . C131 C 0.7176(4) 0.1434(4) 0.61566(10) 0.0183 1.0000 Uani . U . . . . . C141 C 0.7203(4) 0.1109(4) 0.66954(11) 0.0163 1.0000 Uani . U . . . . . C151 C 0.8716(4) 0.0620(5) 0.68943(11) 0.0232 1.0000 Uani . U . . . . . C161 C 1.0191(4) 0.0517(5) 0.65799(12) 0.0257 1.0000 Uani . U . . . . . C171 C 1.0172(4) 0.0904(5) 0.60544(11) 0.0233 1.0000 Uani . U . . . . . C181 C 0.8661(4) 0.1317(5) 0.58364(12) 0.0240 1.0000 Uani . U . . . . . C191 C 0.5760(4) 0.1236(4) 0.70945(10) 0.0172 1.0000 Uani . U . . . . . C201 C 0.3022(4) 0.2090(5) 0.72197(12) 0.0252 1.0000 Uani D U . . . . . N12 N 0.0977(3) -0.2185(4) 0.61755(9) 0.0237 1.0000 Uani . . . . . . . O12 O -0.0367(2) -0.1546(3) 0.72421(7) 0.0234 1.0000 Uani . U . . . . . O22 O 0.1700(2) -0.1833(3) 0.78687(7) 0.0264 1.0000 Uani D U . . . . . C12 C -0.0052(4) -0.2990(5) 0.63921(10) 0.0216 1.0000 Uani . U . . . . . C22 C 0.0312(4) -0.3687(4) 0.68146(10) 0.0220 1.0000 Uani . U . . . . . C32 C -0.1019(4) -0.4338(4) 0.69764(11) 0.0212 1.0000 Uani . U . . . . . C42 C -0.2653(4) -0.4354(4) 0.67290(11) 0.0223 1.0000 Uani . U . . . . . C52 C -0.2963(4) -0.3694(4) 0.62890(10) 0.0231 1.0000 Uani . U . . . . . C62 C -0.1647(4) -0.3049(5) 0.61061(11) 0.0193 1.0000 Uani . U . . . . . C72 C -0.1462(3) -0.2299(5) 0.56603(11) 0.0204 1.0000 Uani . U . . . . . C82 C -0.2505(4) -0.2092(5) 0.52061(10) 0.0264 1.0000 Uani . U . . . . . C92 C -0.1930(4) -0.1372(5) 0.48297(10) 0.0249 1.0000 Uani . U . . . . . C102 C -0.0419(4) -0.0781(4) 0.49165(11) 0.0222 1.0000 Uani . U . . . . . C112 C 0.0643(4) -0.0985(5) 0.53637(10) 0.0220 1.0000 Uani . U . . . . . C122 C 0.0127(3) -0.1761(4) 0.57199(10) 0.0190 1.0000 Uani . U . . . . . C132 C 0.2542(3) -0.1801(5) 0.64157(10) 0.0206 1.0000 Uani . U . . . . . C142 C 0.2663(3) -0.1644(4) 0.69820(10) 0.0192 1.0000 Uani . U . . . . . C152 C 0.4260(3) -0.1357(5) 0.72048(11) 0.0173 1.0000 Uani . U . . . . . C162 C 0.5688(4) -0.1164(5) 0.68788(11) 0.0258 1.0000 Uani . U . . . . . C172 C 0.5504(4) -0.1232(5) 0.63276(11) 0.0274 1.0000 Uani . U . . . . . C182 C 0.3975(4) -0.1562(5) 0.60950(11) 0.0245 1.0000 Uani . U . . . . . C192 C 0.1144(3) -0.1678(4) 0.73597(10) 0.0204 1.0000 Uani . U . . . . . C202 C 0.0396(4) -0.1709(4) 0.82922(10) 0.0250 1.0000 Uani D U . . . . . H211 H 0.6276 -0.0129 0.5399 0.0275 1.0000 Uiso R . . . . . . H311 H 0.4625 -0.0771 0.4664 0.0315 1.0000 Uiso R . . . . . . H411 H 0.2380 0.0257 0.4298 0.0300 1.0000 Uiso R . . . . . . H511 H 0.1406 0.1781 0.4747 0.0272 1.0000 Uiso R . . . . . . H811 H 0.0914 0.3466 0.5497 0.0259 1.0000 Uiso R . . . . . . H911 H 0.1414 0.4927 0.6063 0.0271 1.0000 Uiso R . . . . . . H1011 H 0.3932 0.5005 0.6596 0.0293 1.0000 Uiso R . . . . . . H1111 H 0.6038 0.3658 0.6546 0.0301 1.0000 Uiso R . . . . . . H1511 H 0.8727 0.0353 0.7255 0.0278 1.0000 Uiso R . . . . . . H1611 H 1.1210 0.0184 0.6722 0.0309 1.0000 Uiso R . . . . . . H1711 H 1.1210 0.0885 0.5843 0.0278 1.0000 Uiso R . . . . . . H1811 H 0.8631 0.1522 0.5465 0.0289 1.0000 Uiso R . . . . . . H2011 H 0.1890(19) 0.1728(19) 0.7184(10) 0.0500(15) 1.0000 Uiso D . . . . . . H2012 H 0.345(3) 0.206(3) 0.7595(4) 0.0497(15) 1.0000 Uiso D . . . . . . H2013 H 0.290(3) 0.2836(10) 0.7097(10) 0.0499(16) 1.0000 Uiso D . . . . . . H221 H 0.1430 -0.3709 0.6982 0.0265 1.0000 Uiso R . . . . . . H321 H -0.0821 -0.4807 0.7274 0.0254 1.0000 Uiso R . . . . . . H421 H -0.3547 -0.4814 0.6861 0.0267 1.0000 Uiso R . . . . . . H521 H -0.4074 -0.3690 0.6117 0.0278 1.0000 Uiso R . . . . . . H821 H -0.3594 -0.2447 0.5161 0.0317 1.0000 Uiso R . . . . . . H921 H -0.2573 -0.1275 0.4504 0.0298 1.0000 Uiso R . . . . . . H1021 H -0.0105 -0.0230 0.4668 0.0266 1.0000 Uiso R . . . . . . H1121 H 0.1696 -0.0595 0.5419 0.0264 1.0000 Uiso R . . . . . . H1521 H 0.4370 -0.1292 0.7587 0.0208 1.0000 Uiso R . . . . . . H1621 H 0.6786 -0.0986 0.7035 0.0309 1.0000 Uiso R . . . . . . H1721 H 0.6463 -0.1045 0.6101 0.0331 1.0000 Uiso R . . . . . . H1821 H 0.3895 -0.1627 0.5712 0.0294 1.0000 Uiso R . . . . . . H2021 H 0.095(2) -0.141(3) 0.8619(6) 0.0498(15) 1.0000 Uiso D . . . . . . H2022 H -0.010(3) -0.2419(10) 0.8373(10) 0.0498(16) 1.0000 Uiso D . . . . . . H2023 H -0.055(3) -0.123(2) 0.8169(8) 0.0498(16) 1.0000 Uiso D . . . . . . 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 0.0217(11) 0.0258(19) 0.0188(10) -0.0010(12) -0.0018(9) 0.0015(11) O11 0.0263(10) 0.048(4) 0.0210(9) 0.0091(13) 0.0005(8) 0.0014(14) O21 0.0228(10) 0.041(4) 0.0235(11) 0.0047(12) 0.0005(7) 0.0105(14) C11 0.0233(13) 0.031(3) 0.0122(13) -0.0004(15) 0.0023(10) 0.0021(17) C21 0.0248(14) 0.027(3) 0.0167(13) 0.0035(16) 0.0050(11) -0.0011(19) C31 0.0295(15) 0.030(4) 0.0195(14) -0.0038(15) 0.0067(11) -0.0008(18) C41 0.0279(15) 0.034(4) 0.0127(14) 0.0004(16) 0.0018(11) -0.0077(19) C51 0.0244(14) 0.028(4) 0.0153(13) 0.0070(16) -0.0019(11) -0.003(2) C61 0.0207(13) 0.032(3) 0.0162(13) 0.0008(15) 0.0007(10) -0.0006(17) C71 0.0212(12) 0.033(3) 0.0098(11) 0.0028(15) 0.0031(10) 0.0036(17) C81 0.0219(14) 0.025(4) 0.0176(13) 0.0023(17) 0.0029(11) -0.0007(16) C91 0.0225(13) 0.027(4) 0.0184(14) 0.0005(16) 0.0054(10) -0.0006(18) C101 0.0245(14) 0.033(4) 0.0160(12) -0.0027(17) 0.0046(11) -0.0022(17) C111 0.0233(14) 0.037(4) 0.0152(13) -0.0062(17) 0.0012(11) -0.0003(16) C121 0.0171(12) 0.026(3) 0.0162(13) 0.0005(15) 0.0023(10) 0.0002(16) C131 0.0190(12) 0.016(5) 0.0203(12) -0.0039(15) -0.0033(9) -0.0020(16) C141 0.0205(13) 0.008(5) 0.0204(12) -0.0032(14) -0.0035(10) -0.0052(16) C151 0.0243(14) 0.025(6) 0.0207(14) 0.0039(16) -0.0041(10) 0.0000(17) C161 0.0224(14) 0.018(6) 0.0365(16) -0.0021(16) -0.0019(12) 0.003(2) C171 0.0232(14) 0.017(6) 0.0300(14) -0.0102(16) 0.0064(11) 0.0041(18) C181 0.0271(13) 0.020(6) 0.0253(15) -0.0007(17) 0.0034(10) 0.0012(18) C191 0.0198(12) 0.010(5) 0.0218(11) -0.0014(15) -0.0033(9) -0.0051(17) C201 0.0182(15) 0.024(6) 0.0333(17) 0.0001(17) 0.0025(12) 0.0018(18) N12 0.0214(12) 0.033(5) 0.0163(12) -0.0003(14) 0.0002(10) -0.0060(18) O12 0.0184(8) 0.028(4) 0.0242(10) -0.0037(11) 0.0000(8) -0.0027(14) O22 0.0219(10) 0.043(4) 0.0140(8) 0.0014(12) 0.0031(7) 0.0034(14) C12 0.0225(13) 0.030(3) 0.0118(12) -0.0028(15) 0.0021(10) -0.0019(16) C22 0.0244(14) 0.021(4) 0.0201(14) -0.0038(15) 0.0008(11) 0.0026(17) C32 0.0305(14) 0.016(5) 0.0172(13) -0.0024(15) 0.0001(11) 0.0029(18) C42 0.0289(14) 0.016(5) 0.0220(15) -0.0035(15) 0.0015(11) -0.0062(19) C52 0.0240(14) 0.027(5) 0.0177(14) -0.0035(15) -0.0020(11) -0.0028(17) C62 0.0229(13) 0.017(4) 0.0182(13) -0.0062(14) 0.0003(10) 0.0021(16) C72 0.0224(13) 0.020(4) 0.0189(13) -0.0034(14) -0.0003(10) 0.0028(16) C82 0.0253(14) 0.034(5) 0.0205(14) -0.0024(15) -0.0040(11) -0.0013(19) C92 0.0317(15) 0.026(5) 0.0166(14) -0.0046(14) -0.0021(11) 0.0053(19) C102 0.0273(15) 0.017(5) 0.0221(14) -0.0006(15) 0.0039(11) 0.0094(18) C112 0.0222(14) 0.022(4) 0.0223(14) -0.0036(15) 0.0032(10) 0.0022(17) C122 0.0210(13) 0.024(4) 0.0120(12) -0.0047(14) -0.0001(10) 0.0028(16) C132 0.0165(12) 0.024(3) 0.0208(11) -0.0008(15) -0.0014(10) 0.0042(17) C142 0.0204(11) 0.019(4) 0.0187(11) 0.0019(16) 0.0007(9) 0.0021(18) C152 0.0232(13) 0.006(6) 0.0229(14) 0.0022(14) -0.0009(9) -0.0003(19) C162 0.0196(14) 0.029(6) 0.0289(12) -0.0044(17) -0.0014(10) -0.006(2) C172 0.0194(13) 0.036(6) 0.0263(12) 0.0038(17) 0.0059(11) -0.0002(19) C182 0.0276(13) 0.029(4) 0.0167(12) -0.0015(17) 0.0027(9) -0.002(2) C192 0.0211(10) 0.024(5) 0.0156(11) 0.0023(17) -0.0007(9) -0.003(2) C202 0.0226(14) 0.038(5) 0.0140(13) -0.0073(17) 0.0043(10) 0.001(2) _refine_ls_extinction_method None #_oxford_refine_ls_scale 3.351(6) 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 N11 . C11 . 1.393(5) yes N11 . C121 . 1.382(6) yes N11 . C131 . 1.424(4) yes O11 . C191 . 1.210(3) yes O21 . C191 . 1.321(4) yes O21 . C201 . 1.441(5) yes C11 . C21 . 1.373(8) yes C11 . C61 . 1.390(6) yes C21 . C31 . 1.389(5) yes C21 . H211 . 0.950 no C31 . C41 . 1.385(6) yes C31 . H311 . 0.950 no C41 . C51 . 1.366(8) yes C41 . H411 . 0.950 no C51 . C61 . 1.397(5) yes C51 . H511 . 0.950 no C61 . C71 . 1.442(8) yes C71 . C81 . 1.356(6) yes C71 . C121 . 1.409(4) yes C81 . C91 . 1.376(7) yes C81 . H811 . 0.950 no C91 . C101 . 1.395(4) yes C91 . H911 . 0.950 no C101 . C111 . 1.371(6) yes C101 . H1011 . 0.950 no C111 . C121 . 1.397(7) yes C111 . H1111 . 0.950 no C131 . C141 . 1.389(4) yes C131 . C181 . 1.391(4) yes C141 . C151 . 1.397(5) yes C141 . C191 . 1.487(4) yes C151 . C161 . 1.375(4) yes C151 . H1511 . 0.950 no C161 . C171 . 1.382(5) yes C161 . H1611 . 0.950 no C171 . C181 . 1.374(5) yes C171 . H1711 . 0.950 no C181 . H1811 . 0.950 no C201 . H2011 . 0.980(8) no C201 . H2012 . 0.981(8) no C201 . H2013 . 0.981(8) no N12 . C12 . 1.382(6) yes N12 . C122 . 1.401(4) yes N12 . C132 . 1.418(4) yes O12 . C192 . 1.203(3) yes O22 . C192 . 1.339(3) yes O22 . C202 . 1.452(3) yes C12 . C22 . 1.384(6) yes C12 . C62 . 1.411(4) yes C22 . C32 . 1.361(6) yes C22 . H221 . 0.950 no C32 . C42 . 1.391(4) yes C32 . H321 . 0.950 no C42 . C52 . 1.381(6) yes C42 . H421 . 0.950 no C52 . C62 . 1.365(6) yes C52 . H521 . 0.950 no C62 . C72 . 1.449(6) yes C72 . C82 . 1.398(4) yes C72 . C122 . 1.396(5) yes C82 . C92 . 1.363(7) yes C82 . H821 . 0.950 no C92 . C102 . 1.387(6) yes C92 . H921 . 0.950 no C102 . C112 . 1.393(4) yes C102 . H1021 . 0.950 no C112 . C122 . 1.364(6) yes C112 . H1121 . 0.950 no C132 . C142 . 1.413(4) yes C132 . C182 . 1.384(4) yes C142 . C152 . 1.386(4) yes C142 . C192 . 1.489(4) yes C152 . C162 . 1.377(4) yes C152 . H1521 . 0.950 no C162 . C172 . 1.369(4) yes C162 . H1621 . 0.950 no C172 . C182 . 1.365(4) yes C172 . H1721 . 0.950 no C182 . H1821 . 0.950 no C202 . H2021 . 0.982(8) no C202 . H2022 . 0.983(8) no C202 . H2023 . 0.983(8) 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 C11 . N11 . C121 . 109.2(3) yes C11 . N11 . C131 . 120.8(4) yes C121 . N11 . C131 . 130.0(3) yes C191 . O21 . C201 . 118.0(2) yes N11 . C11 . C21 . 129.5(3) yes N11 . C11 . C61 . 108.4(4) yes C21 . C11 . C61 . 122.1(3) yes C11 . C21 . C31 . 117.3(4) yes C11 . C21 . H211 . 121.3 no C31 . C21 . H211 . 121.3 no C21 . C31 . C41 . 121.3(5) yes C21 . C31 . H311 . 119.3 no C41 . C31 . H311 . 119.3 no C31 . C41 . C51 . 120.5(3) yes C31 . C41 . H411 . 119.7 no C51 . C41 . H411 . 119.7 no C41 . C51 . C61 . 119.2(4) yes C41 . C51 . H511 . 120.4 no C61 . C51 . H511 . 120.4 no C51 . C61 . C11 . 119.1(5) yes C51 . C61 . C71 . 133.4(4) yes C11 . C61 . C71 . 107.4(3) yes C61 . C71 . C81 . 133.4(3) yes C61 . C71 . C121 . 106.6(4) yes C81 . C71 . C121 . 120.0(4) yes C71 . C81 . C91 . 119.6(3) yes C71 . C81 . H811 . 120.2 no C91 . C81 . H811 . 120.2 no C81 . C91 . C101 . 120.5(4) yes C81 . C91 . H911 . 119.8 no C101 . C91 . H911 . 119.8 no C91 . C101 . C111 . 121.2(4) yes C91 . C101 . H1011 . 119.4 no C111 . C101 . H1011 . 119.4 no C101 . C111 . C121 . 117.7(3) yes C101 . C111 . H1111 . 121.1 no C121 . C111 . H1111 . 121.1 no C71 . C121 . C111 . 120.6(4) yes C71 . C121 . N11 . 108.3(4) yes C111 . C121 . N11 . 131.1(3) yes N11 . C131 . C141 . 122.6(3) yes N11 . C131 . C181 . 117.3(2) yes C141 . C131 . C181 . 120.0(3) yes C131 . C141 . C151 . 118.4(3) yes C131 . C141 . C191 . 126.2(3) yes C151 . C141 . C191 . 115.4(3) yes C141 . C151 . C161 . 121.5(3) yes C141 . C151 . H1511 . 119.2 no C161 . C151 . H1511 . 119.2 no C151 . C161 . C171 . 119.2(3) yes C151 . C161 . H1611 . 120.4 no C171 . C161 . H1611 . 120.4 no C161 . C171 . C181 . 120.4(3) yes C161 . C171 . H1711 . 119.8 no C181 . C171 . H1711 . 119.8 no C131 . C181 . C171 . 120.3(3) yes C131 . C181 . H1811 . 119.9 no C171 . C181 . H1811 . 119.9 no C141 . C191 . O21 . 114.2(2) yes C141 . C191 . O11 . 121.8(3) yes O21 . C191 . O11 . 123.9(3) yes O21 . C201 . H2011 . 107.7(12) no O21 . C201 . H2012 . 108.4(12) no H2011 . C201 . H2012 . 111.4(13) no O21 . C201 . H2013 . 109.8(12) no H2011 . C201 . H2013 . 108.8(13) no H2012 . C201 . H2013 . 110.8(13) no C12 . N12 . C122 . 108.6(2) yes C12 . N12 . C132 . 124.3(3) yes C122 . N12 . C132 . 126.8(4) yes C192 . O22 . C202 . 116.1(2) yes N12 . C12 . C22 . 129.1(3) yes N12 . C12 . C62 . 109.6(3) yes C22 . C12 . C62 . 121.2(4) yes C12 . C22 . C32 . 116.3(3) yes C12 . C22 . H221 . 121.8 no C32 . C22 . H221 . 121.8 no C22 . C32 . C42 . 123.5(4) yes C22 . C32 . H321 . 118.3 no C42 . C32 . H321 . 118.3 no C32 . C42 . C52 . 119.4(4) yes C32 . C42 . H421 . 120.3 no C52 . C42 . H421 . 120.3 no C42 . C52 . C62 . 118.9(3) yes C42 . C52 . H521 . 120.6 no C62 . C52 . H521 . 120.6 no C12 . C62 . C52 . 120.2(3) yes C12 . C62 . C72 . 105.2(3) yes C52 . C62 . C72 . 134.6(3) yes C62 . C72 . C82 . 132.1(4) yes C62 . C72 . C122 . 108.3(3) yes C82 . C72 . C122 . 119.5(4) yes C72 . C82 . C92 . 118.8(4) yes C72 . C82 . H821 . 120.6 no C92 . C82 . H821 . 120.6 no C82 . C92 . C102 . 120.9(3) yes C82 . C92 . H921 . 119.6 no C102 . C92 . H921 . 119.6 no C92 . C102 . C112 . 120.7(4) yes C92 . C102 . H1021 . 119.6 no C112 . C102 . H1021 . 119.6 no C102 . C112 . C122 . 118.0(4) yes C102 . C112 . H1121 . 121.0 no C122 . C112 . H1121 . 121.0 no N12 . C122 . C72 . 107.9(4) yes N12 . C122 . C112 . 130.5(3) yes C72 . C122 . C112 . 121.6(3) yes N12 . C132 . C142 . 121.0(2) yes N12 . C132 . C182 . 120.2(2) yes C142 . C132 . C182 . 118.9(3) yes C132 . C142 . C152 . 119.0(2) yes C132 . C142 . C192 . 124.2(2) yes C152 . C142 . C192 . 116.5(2) yes C142 . C152 . C162 . 120.8(2) yes C142 . C152 . H1521 . 119.6 no C162 . C152 . H1521 . 119.6 no C152 . C162 . C172 . 119.2(3) yes C152 . C162 . H1621 . 120.4 no C172 . C162 . H1621 . 120.4 no C162 . C172 . C182 . 121.6(3) yes C162 . C172 . H1721 . 119.2 no C182 . C172 . H1721 . 119.2 no C132 . C182 . C172 . 120.2(3) yes C132 . C182 . H1821 . 119.9 no C172 . C182 . H1821 . 119.9 no C142 . C192 . O22 . 110.0(2) yes C142 . C192 . O12 . 126.5(3) yes O22 . C192 . O12 . 123.4(2) yes O22 . C202 . H2021 . 109.4(11) no O22 . C202 . H2022 . 108.5(12) no H2021 . C202 . H2022 . 109.9(13) no O22 . C202 . H2023 . 110.4(12) no H2021 . C202 . H2023 . 110.2(13) no H2022 . C202 . H2023 . 108.4(13) no _chemical_name_common 'Methyl 2-(9H-carbazol-9-yl)benzoate' _exptl_crystal_recrystallization_method ; A mixture of carbazole, methyl 2-iodobenzoate, copper powder, potassium carbonate and nitrobenzene were heated at 175 degrees C for 48 h. After cooling, the resultant mixture was a red solid. A mixture of water/chloroform (1:1) was added to the solid, and the two layers separated. The aqueous layer was then extracted twice with chloroform, and the organic layers were combined and dried over MgSO4. The solvent was removed under reduced pressure, and the residue oil was purified by flash dry chromatography on silica using hexane/ethyl acetate (85:15) as the eluant. This resulted in the formation of colourless crystals. (5.30 g, 88%) ; #edit data_6_8GPa_II.cif _database_code_depnum_ccdc_archive 'CCDC 752562' #_oxford_structure_analysis_title 'benm07 in P2(1)2(1)2(1)' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 7.6285(8) _cell_length_b 12.299(3) _cell_length_c 24.555(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2303.9(7) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,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 0.0010 0.0010 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0020 0.0020 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0020 0.0010 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C20 H15 N1 O2 # Dc = 1.74 Fooo = 1264.00 Mu = 1.12 M = 602.69 # Found Formula = C20 H15 N1 O2 # Dc = 1.74 FOOO = 1264.00 Mu = 1.12 M = 602.69 _chemical_formula_sum 'C20 H15 N1 O2' _chemical_formula_moiety 'C20 H15 N1 O2' _chemical_compound_source ? _chemical_formula_weight 301.34 _cell_measurement_reflns_used 2637 _cell_measurement_theta_min 2 _cell_measurement_theta_max 15 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.737 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.112 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device APEX-II _diffrn_measurement_device_type Area _diffrn_radiation_monochromator silicon _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.47920 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 293 _diffrn_ambient_pressure 6800000 _diffrn_reflns_number 11286 _reflns_number_total 1167 _diffrn_reflns_av_R_equivalents 0.0962 # Number of reflections with Friedels Law is 1167 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1659 _diffrn_reflns_reduction_process ; Merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 ; _diffrn_reflns_theta_min 1.118 _diffrn_reflns_theta_max 15.467 _diffrn_measured_fraction_theta_max 0.602 _diffrn_reflns_theta_full 11.755 _diffrn_measured_fraction_theta_full 0.632 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 27 _reflns_limit_h_min 0 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 27 #_oxford_diffrn_Wilson_B_factor 0.00 #_oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.15 _refine_diff_density_max 0.14 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement #_oxford_reflns_threshold_expression_ref I>2.0\s(I) _refine_ls_number_reflns 1026 _refine_ls_number_restraints 462 _refine_ls_number_parameters 439 #_oxford_refine_ls_R_factor_ref 0.0316 _refine_ls_wR_factor_ref 0.0276 _refine_ls_goodness_of_fit_ref 1.0841 _refine_ls_shift/su_max 0.000351 # The values computed from all data #_oxford_reflns_number_all 1140 _refine_ls_R_factor_all 0.0408 _refine_ls_wR_factor_all 0.0355 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1026 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_gt 0.0276 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 5.62 -5.04 1.90 ; 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens N11 N 0.5657(4) 0.1817(5) 0.58931(11) 0.0227 1.0000 Uani . U . . . . . O11 O 0.5993(3) 0.1130(4) 0.75761(9) 0.0281 1.0000 Uani . U . . . . . O21 O 0.4251(3) 0.1519(4) 0.68687(8) 0.0294 1.0000 Uani D U . . . . . C11 C 0.4859(4) 0.1232(6) 0.54798(13) 0.0200 1.0000 Uani . U . . . . . C21 C 0.5350(5) 0.0252(6) 0.52548(13) 0.0216 1.0000 Uani . U . . . . . C31 C 0.4381(5) -0.0118(6) 0.48179(13) 0.0221 1.0000 Uani . U . . . . . C41 C 0.2980(5) 0.0486(6) 0.46157(13) 0.0246 1.0000 Uani . U . . . . . C51 C 0.2413(5) 0.1392(6) 0.48647(13) 0.0228 1.0000 Uani . U . . . . . C61 C 0.3370(4) 0.1778(6) 0.53134(13) 0.0194 1.0000 Uani . U . . . . . C71 C 0.3195(4) 0.2732(6) 0.56538(13) 0.0191 1.0000 Uani . U . . . . . C81 C 0.1948(4) 0.3525(6) 0.57027(13) 0.0173 1.0000 Uani . U . . . . . C91 C 0.2228(5) 0.4385(6) 0.60498(12) 0.0185 1.0000 Uani . U . . . . . C101 C 0.3764(4) 0.4440(6) 0.63598(13) 0.0216 1.0000 Uani . U . . . . . C111 C 0.5008(5) 0.3632(6) 0.63316(13) 0.0209 1.0000 Uani . U . . . . . C121 C 0.4691(4) 0.2753(6) 0.59935(13) 0.0212 1.0000 Uani . U . . . . . C131 C 0.7209(4) 0.1415(5) 0.61491(13) 0.0194 1.0000 Uani . U . . . . . C141 C 0.7216(5) 0.1113(6) 0.66934(14) 0.0192 1.0000 Uani . U . . . . . C151 C 0.8732(5) 0.0631(6) 0.68986(14) 0.0242 1.0000 Uani . U . . . . . C161 C 1.0200(5) 0.0528(6) 0.65854(13) 0.0236 1.0000 Uani . U . . . . . C171 C 1.0201(5) 0.0892(6) 0.60563(13) 0.0227 1.0000 Uani . U . . . . . C181 C 0.8689(4) 0.1320(6) 0.58358(14) 0.0231 1.0000 Uani . U . . . . . C191 C 0.5769(4) 0.1245(6) 0.70911(13) 0.0185 1.0000 Uani . U . . . . . C201 C 0.3015(5) 0.2104(6) 0.72110(14) 0.0225 1.0000 Uani D U . . . . . N12 N 0.0974(4) -0.2194(5) 0.61733(11) 0.0241 1.0000 Uani . . . . . . . O12 O -0.0364(3) -0.1561(4) 0.72437(8) 0.0211 1.0000 Uani . U . . . . . O22 O 0.1712(3) -0.1838(4) 0.78750(8) 0.0226 1.0000 Uani D U . . . . . C12 C -0.0057(5) -0.2980(6) 0.63961(13) 0.0221 1.0000 Uani . U . . . . . C22 C 0.0294(5) -0.3688(6) 0.68211(13) 0.0257 1.0000 Uani . U . . . . . C32 C -0.1046(5) -0.4332(6) 0.69832(14) 0.0220 1.0000 Uani . U . . . . . C42 C -0.2697(5) -0.4344(6) 0.67385(14) 0.0228 1.0000 Uani . U . . . . . C52 C -0.3001(5) -0.3699(6) 0.62988(12) 0.0243 1.0000 Uani . U . . . . . C62 C -0.1661(4) -0.3047(6) 0.61092(13) 0.0191 1.0000 Uani . U . . . . . C72 C -0.1483(4) -0.2291(6) 0.56604(14) 0.0190 1.0000 Uani . U . . . . . C82 C -0.2520(5) -0.2075(6) 0.52037(12) 0.0256 1.0000 Uani . U . . . . . C92 C -0.1924(5) -0.1364(6) 0.48197(13) 0.0237 1.0000 Uani . U . . . . . C102 C -0.0399(5) -0.0781(6) 0.49054(14) 0.0251 1.0000 Uani . U . . . . . C112 C 0.0650(5) -0.0967(6) 0.53532(13) 0.0213 1.0000 Uani . U . . . . . C122 C 0.0115(4) -0.1758(6) 0.57162(12) 0.0205 1.0000 Uani . U . . . . . C132 C 0.2551(4) -0.1789(6) 0.64180(12) 0.0223 1.0000 Uani . U . . . . . C142 C 0.2661(4) -0.1642(6) 0.69884(13) 0.0225 1.0000 Uani . U . . . . . C152 C 0.4279(4) -0.1354(6) 0.72046(13) 0.0259 1.0000 Uani . U . . . . . C162 C 0.5702(4) -0.1156(6) 0.68836(14) 0.0183 1.0000 Uani . U . . . . . C172 C 0.5505(5) -0.1220(6) 0.63264(14) 0.0269 1.0000 Uani . U . . . . . C182 C 0.3979(4) -0.1541(6) 0.60950(14) 0.0254 1.0000 Uani . U . . . . . C192 C 0.1147(4) -0.1685(6) 0.73628(12) 0.0236 1.0000 Uani . U . . . . . C202 C 0.0406(5) -0.1696(6) 0.82936(13) 0.0315 1.0000 Uani D U . . . . . H211 H 0.6314 -0.0150 0.5394 0.0261 1.0000 Uiso R . . . . . . H311 H 0.4673 -0.0793 0.4653 0.0264 1.0000 Uiso R . . . . . . H411 H 0.2409 0.0251 0.4293 0.0294 1.0000 Uiso R . . . . . . H511 H 0.1396 0.1763 0.4741 0.0275 1.0000 Uiso R . . . . . . H811 H 0.0894 0.3481 0.5498 0.0210 1.0000 Uiso R . . . . . . H911 H 0.1376 0.4945 0.6079 0.0219 1.0000 Uiso R . . . . . . H1011 H 0.3951 0.5044 0.6594 0.0258 1.0000 Uiso R . . . . . . H1111 H 0.6057 0.3676 0.6539 0.0250 1.0000 Uiso R . . . . . . H1511 H 0.8743 0.0372 0.7263 0.0288 1.0000 Uiso R . . . . . . H1611 H 1.1222 0.0200 0.6733 0.0282 1.0000 Uiso R . . . . . . H1711 H 1.1239 0.0852 0.5844 0.0276 1.0000 Uiso R . . . . . . H1811 H 0.8672 0.1549 0.5466 0.0278 1.0000 Uiso R . . . . . . H2011 H 0.1868(19) 0.175(2) 0.7177(12) 0.0500(15) 1.0000 Uiso D . . . . . . H2012 H 0.343(3) 0.209(3) 0.7589(4) 0.0499(15) 1.0000 Uiso D . . . . . . H2013 H 0.294(4) 0.2856(11) 0.7078(12) 0.0498(15) 1.0000 Uiso D . . . . . . H221 H 0.1415 -0.3720 0.6989 0.0307 1.0000 Uiso R . . . . . . H321 H -0.0849 -0.4806 0.7282 0.0260 1.0000 Uiso R . . . . . . H421 H -0.3599 -0.4798 0.6878 0.0277 1.0000 Uiso R . . . . . . H521 H -0.4114 -0.3697 0.6126 0.0288 1.0000 Uiso R . . . . . . H821 H -0.3628 -0.2418 0.5162 0.0311 1.0000 Uiso R . . . . . . H921 H -0.2562 -0.1269 0.4491 0.0292 1.0000 Uiso R . . . . . . H1021 H -0.0065 -0.0239 0.4650 0.0302 1.0000 Uiso R . . . . . . H1121 H 0.1699 -0.0567 0.5410 0.0257 1.0000 Uiso R . . . . . . H1521 H 0.4397 -0.1293 0.7589 0.0316 1.0000 Uiso R . . . . . . H1621 H 0.6804 -0.0978 0.7040 0.0221 1.0000 Uiso R . . . . . . H1721 H 0.6465 -0.1032 0.6099 0.0313 1.0000 Uiso R . . . . . . H1821 H 0.3891 -0.1599 0.5710 0.0305 1.0000 Uiso R . . . . . . H2021 H 0.097(3) -0.138(3) 0.8615(8) 0.0497(15) 1.0000 Uiso D . . . . . . H2022 H -0.009(4) -0.2407(12) 0.8386(12) 0.0498(15) 1.0000 Uiso D . . . . . . H2023 H -0.052(3) -0.121(3) 0.8159(9) 0.0498(15) 1.0000 Uiso D . . . . . . 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 0.0212(13) 0.028(2) 0.0188(12) -0.0052(15) -0.0021(11) 0.0022(13) O11 0.0244(13) 0.041(5) 0.0194(10) 0.0032(16) -0.0004(10) -0.0022(18) O21 0.0211(12) 0.047(6) 0.0205(12) 0.0049(16) 0.0009(9) 0.0093(17) C11 0.0223(16) 0.024(4) 0.0139(15) -0.001(2) 0.0015(12) -0.001(2) C21 0.0203(17) 0.024(4) 0.0210(17) -0.001(2) 0.0026(13) 0.000(2) C31 0.0278(18) 0.018(5) 0.0207(17) -0.0035(19) 0.0070(13) -0.010(2) C41 0.0285(19) 0.032(6) 0.0130(17) -0.004(2) -0.0014(14) -0.012(2) C51 0.0224(18) 0.027(5) 0.0186(16) 0.003(2) -0.0027(13) -0.006(2) C61 0.0205(16) 0.025(4) 0.0132(15) 0.0004(19) 0.0019(12) -0.002(2) C71 0.0175(15) 0.023(4) 0.0165(16) 0.001(2) 0.0019(12) -0.0019(19) C81 0.0167(16) 0.017(4) 0.0179(16) 0.006(2) 0.0007(13) -0.0045(18) C91 0.0197(15) 0.019(4) 0.0167(16) 0.004(2) 0.0039(12) -0.002(2) C101 0.0203(17) 0.025(5) 0.0198(16) -0.002(2) 0.0036(13) -0.003(2) C111 0.0198(17) 0.026(4) 0.0168(16) -0.001(2) 0.0004(13) -0.0026(19) C121 0.0172(15) 0.031(4) 0.0159(16) -0.005(2) 0.0018(12) 0.003(2) C131 0.0204(14) 0.020(6) 0.0180(13) -0.0039(19) -0.0024(10) 0.000(2) C141 0.0192(15) 0.019(7) 0.0196(14) -0.0014(19) 0.0000(11) -0.006(2) C151 0.0209(17) 0.032(7) 0.0200(17) 0.002(2) -0.0043(12) -0.005(2) C161 0.0218(17) 0.021(8) 0.0279(17) -0.004(2) -0.0041(13) 0.008(2) C171 0.0235(17) 0.017(8) 0.0277(17) -0.003(2) 0.0056(14) 0.006(2) C181 0.0262(16) 0.022(7) 0.0210(17) 0.005(2) 0.0029(12) 0.003(2) C191 0.0198(15) 0.015(7) 0.0206(12) 0.000(2) -0.0012(11) -0.001(2) C201 0.0188(19) 0.017(8) 0.032(2) 0.006(2) 0.0019(15) 0.002(2) N12 0.0184(15) 0.037(7) 0.0171(14) 0.004(2) -0.0021(12) -0.010(2) O12 0.0174(10) 0.024(5) 0.0219(12) -0.0020(15) 0.0011(9) -0.0021(17) O22 0.0193(12) 0.034(5) 0.0147(10) -0.0007(16) 0.0025(8) -0.0006(16) C12 0.0205(15) 0.032(4) 0.0140(15) -0.004(2) 0.0003(13) 0.0007(19) C22 0.0236(17) 0.035(5) 0.0183(17) 0.001(2) 0.0018(14) 0.000(2) C32 0.0248(16) 0.024(6) 0.0172(17) -0.007(2) 0.0000(13) 0.000(2) C42 0.0193(15) 0.027(6) 0.0221(18) 0.002(2) 0.0029(13) 0.000(2) C52 0.0239(18) 0.033(6) 0.0158(17) -0.0004(19) -0.0004(14) -0.003(2) C62 0.0186(15) 0.020(5) 0.0184(16) -0.0036(19) 0.0018(12) 0.0059(19) C72 0.0231(16) 0.014(5) 0.0201(15) -0.0040(18) -0.0005(12) 0.0045(19) C82 0.0253(18) 0.032(6) 0.0198(17) -0.0044(19) -0.0024(13) 0.001(2) C92 0.0259(18) 0.030(6) 0.0156(17) -0.0039(19) -0.0027(14) 0.008(2) C102 0.0250(18) 0.028(6) 0.0218(16) 0.000(2) 0.0033(13) 0.006(2) C112 0.0223(17) 0.020(5) 0.0218(16) -0.0052(19) 0.0021(12) 0.001(2) C122 0.0221(16) 0.027(5) 0.0122(14) -0.0036(17) -0.0003(12) 0.002(2) C132 0.0155(14) 0.033(4) 0.0180(12) 0.000(2) -0.0009(11) 0.001(2) C142 0.0191(13) 0.031(5) 0.0175(12) -0.002(2) -0.0009(11) 0.001(2) C152 0.0217(16) 0.035(8) 0.0209(17) -0.003(2) -0.0021(11) 0.000(3) C162 0.0189(16) 0.005(8) 0.0308(14) 0.003(2) -0.0026(12) 0.002(2) C172 0.0188(16) 0.033(8) 0.0291(14) 0.002(2) 0.0059(14) 0.002(2) C182 0.0233(15) 0.034(4) 0.0194(15) -0.002(2) 0.0055(11) 0.001(2) C192 0.0199(12) 0.035(7) 0.0161(12) -0.002(2) -0.0019(10) -0.006(2) C202 0.0208(18) 0.060(8) 0.0139(15) 0.000(2) 0.0036(13) -0.004(3) _refine_ls_extinction_method None #_oxford_refine_ls_scale 3.567(7) 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 N11 . C11 . 1.385(6) yes N11 . C121 . 1.389(9) yes N11 . C131 . 1.428(5) yes O11 . C191 . 1.211(4) yes O21 . C191 . 1.324(4) yes O21 . C201 . 1.453(6) yes C11 . C21 . 1.378(10) yes C11 . C61 . 1.381(7) yes C21 . C31 . 1.380(6) yes C21 . H211 . 0.950 no C31 . C41 . 1.393(8) yes C31 . H311 . 0.950 no C41 . C51 . 1.343(10) yes C41 . H411 . 0.950 no C51 . C61 . 1.404(6) yes C51 . H511 . 0.950 no C61 . C71 . 1.448(10) yes C71 . C81 . 1.367(9) yes C71 . C121 . 1.413(5) yes C81 . C91 . 1.375(9) yes C81 . H811 . 0.950 no C91 . C101 . 1.399(5) yes C91 . H911 . 0.950 no C101 . C111 . 1.376(9) yes C101 . H1011 . 0.950 no C111 . C121 . 1.384(9) yes C111 . H1111 . 0.950 no C131 . C141 . 1.387(5) yes C131 . C181 . 1.371(5) yes C141 . C151 . 1.394(6) yes C141 . C191 . 1.483(5) yes C151 . C161 . 1.365(5) yes C151 . H1511 . 0.950 no C161 . C171 . 1.374(6) yes C161 . H1611 . 0.950 no C171 . C181 . 1.378(6) yes C171 . H1711 . 0.950 no C181 . H1811 . 0.950 no C201 . H2011 . 0.979(8) no C201 . H2012 . 0.982(8) no C201 . H2013 . 0.983(8) no N12 . C12 . 1.362(7) yes N12 . C122 . 1.406(5) yes N12 . C132 . 1.434(5) yes O12 . C192 . 1.199(4) yes O22 . C192 . 1.343(4) yes O22 . C202 . 1.442(4) yes C12 . C22 . 1.386(8) yes C12 . C62 . 1.414(5) yes C22 . C32 . 1.353(7) yes C22 . H221 . 0.950 no C32 . C42 . 1.395(5) yes C32 . H321 . 0.950 no C42 . C52 . 1.360(7) yes C42 . H421 . 0.950 no C52 . C62 . 1.380(7) yes C52 . H521 . 0.950 no C62 . C72 . 1.448(8) yes C72 . C82 . 1.398(5) yes C72 . C122 . 1.391(7) yes C82 . C92 . 1.364(8) yes C82 . H821 . 0.950 no C92 . C102 . 1.383(7) yes C92 . H921 . 0.950 no C102 . C112 . 1.379(5) yes C102 . H1021 . 0.950 no C112 . C122 . 1.381(8) yes C112 . H1121 . 0.950 no C132 . C142 . 1.415(5) yes C132 . C182 . 1.381(5) yes C142 . C152 . 1.390(5) yes C142 . C192 . 1.477(5) yes C152 . C162 . 1.363(5) yes C152 . H1521 . 0.950 no C162 . C172 . 1.379(5) yes C162 . H1621 . 0.950 no C172 . C182 . 1.355(6) yes C172 . H1721 . 0.950 no C182 . H1821 . 0.950 no C202 . H2021 . 0.980(8) no C202 . H2022 . 0.981(8) no C202 . H2023 . 0.981(8) 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 C11 . N11 . C121 . 109.1(3) yes C11 . N11 . C131 . 120.5(5) yes C121 . N11 . C131 . 130.4(4) yes C191 . O21 . C201 . 117.0(3) yes N11 . C11 . C21 . 128.9(4) yes N11 . C11 . C61 . 109.0(5) yes C21 . C11 . C61 . 122.0(4) yes C11 . C21 . C31 . 117.1(4) yes C11 . C21 . H211 . 121.4 no C31 . C21 . H211 . 121.5 no C21 . C31 . C41 . 120.8(6) yes C21 . C31 . H311 . 119.6 no C41 . C31 . H311 . 119.6 no C31 . C41 . C51 . 121.8(4) yes C31 . C41 . H411 . 119.1 no C51 . C41 . H411 . 119.0 no C41 . C51 . C61 . 118.0(5) yes C41 . C51 . H511 . 121.0 no C61 . C51 . H511 . 120.9 no C51 . C61 . C11 . 119.7(6) yes C51 . C61 . C71 . 132.8(5) yes C11 . C61 . C71 . 107.4(4) yes C61 . C71 . C81 . 133.9(3) yes C61 . C71 . C121 . 106.3(5) yes C81 . C71 . C121 . 119.8(5) yes C71 . C81 . C91 . 119.6(4) yes C71 . C81 . H811 . 120.1 no C91 . C81 . H811 . 120.2 no C81 . C91 . C101 . 120.3(6) yes C81 . C91 . H911 . 119.9 no C101 . C91 . H911 . 119.8 no C91 . C101 . C111 . 121.0(5) yes C91 . C101 . H1011 . 119.5 no C111 . C101 . H1011 . 119.5 no C101 . C111 . C121 . 118.3(4) yes C101 . C111 . H1111 . 120.9 no C121 . C111 . H1111 . 120.9 no C71 . C121 . N11 . 108.0(5) yes C71 . C121 . C111 . 120.6(6) yes N11 . C121 . C111 . 131.4(3) yes N11 . C131 . C141 . 121.3(3) yes N11 . C131 . C181 . 117.7(3) yes C141 . C131 . C181 . 120.9(4) yes C131 . C141 . C151 . 117.8(3) yes C131 . C141 . C191 . 127.0(4) yes C151 . C141 . C191 . 115.2(3) yes C141 . C151 . C161 . 121.1(4) yes C141 . C151 . H1511 . 119.4 no C161 . C151 . H1511 . 119.5 no C151 . C161 . C171 . 120.2(4) yes C151 . C161 . H1611 . 119.9 no C171 . C161 . H1611 . 119.9 no C161 . C171 . C181 . 119.7(3) yes C161 . C171 . H1711 . 120.2 no C181 . C171 . H1711 . 120.1 no C171 . C181 . C131 . 120.1(3) yes C171 . C181 . H1811 . 120.0 no C131 . C181 . H1811 . 120.0 no C141 . C191 . O21 . 114.0(3) yes C141 . C191 . O11 . 122.0(3) yes O21 . C191 . O11 . 124.0(3) yes O21 . C201 . H2011 . 108.3(13) no O21 . C201 . H2012 . 109.0(12) no H2011 . C201 . H2012 . 111.1(13) no O21 . C201 . H2013 . 108.1(13) no H2011 . C201 . H2013 . 109.5(13) no H2012 . C201 . H2013 . 110.8(13) no C12 . N12 . C122 . 108.8(3) yes C12 . N12 . C132 . 124.3(3) yes C122 . N12 . C132 . 126.4(5) yes C192 . O22 . C202 . 115.4(3) yes N12 . C12 . C22 . 129.6(3) yes N12 . C12 . C62 . 109.9(4) yes C22 . C12 . C62 . 120.4(5) yes C12 . C22 . C32 . 116.3(4) yes C12 . C22 . H221 . 121.8 no C32 . C22 . H221 . 121.9 no C22 . C32 . C42 . 124.2(5) yes C22 . C32 . H321 . 117.9 no C42 . C32 . H321 . 117.9 no C32 . C42 . C52 . 119.3(5) yes C32 . C42 . H421 . 120.4 no C52 . C42 . H421 . 120.3 no C42 . C52 . C62 . 118.7(3) yes C42 . C52 . H521 . 120.6 no C62 . C52 . H521 . 120.6 no C12 . C62 . C52 . 120.4(4) yes C12 . C62 . C72 . 105.1(4) yes C52 . C62 . C72 . 134.4(3) yes C62 . C72 . C82 . 132.8(5) yes C62 . C72 . C122 . 108.0(3) yes C82 . C72 . C122 . 119.1(5) yes C72 . C82 . C92 . 119.2(4) yes C72 . C82 . H821 . 120.4 no C92 . C82 . H821 . 120.4 no C82 . C92 . C102 . 120.5(3) yes C82 . C92 . H921 . 119.7 no C102 . C92 . H921 . 119.8 no C92 . C102 . C112 . 121.5(5) yes C92 . C102 . H1021 . 119.2 no C112 . C102 . H1021 . 119.3 no C102 . C112 . C122 . 117.4(4) yes C102 . C112 . H1121 . 121.3 no C122 . C112 . H1121 . 121.3 no N12 . C122 . C72 . 107.9(5) yes N12 . C122 . C112 . 130.3(4) yes C72 . C122 . C112 . 121.8(4) yes N12 . C132 . C142 . 120.6(3) yes N12 . C132 . C182 . 119.8(3) yes C142 . C132 . C182 . 119.6(4) yes C132 . C142 . C152 . 117.6(3) yes C132 . C142 . C192 . 124.4(3) yes C152 . C142 . C192 . 117.8(3) yes C142 . C152 . C162 . 122.1(3) yes C142 . C152 . H1521 . 118.9 no C162 . C152 . H1521 . 119.0 no C152 . C162 . C172 . 118.5(4) yes C152 . C162 . H1621 . 120.8 no C172 . C162 . H1621 . 120.7 no C162 . C172 . C182 . 121.8(4) yes C162 . C172 . H1721 . 119.1 no C182 . C172 . H1721 . 119.1 no C132 . C182 . C172 . 120.1(3) yes C132 . C182 . H1821 . 120.0 no C172 . C182 . H1821 . 119.9 no C142 . C192 . O22 . 109.7(3) yes C142 . C192 . O12 . 126.5(3) yes O22 . C192 . O12 . 123.7(3) yes O22 . C202 . H2021 . 108.7(12) no O22 . C202 . H2022 . 108.9(13) no H2021 . C202 . H2022 . 109.9(13) no O22 . C202 . H2023 . 109.4(12) no H2021 . C202 . H2023 . 110.0(13) no H2022 . C202 . H2023 . 109.8(13) no _chemical_name_common 'Methyl 2-(9H-carbazol-9-yl)benzoate' _exptl_crystal_recrystallization_method ; A mixture of carbazole, methyl 2-iodobenzoate, copper powder, potassium carbonate and nitrobenzene were heated at 175 degrees C for 48 h. After cooling, the resultant mixture was a red solid. A mixture of water/chloroform (1:1) was added to the solid, and the two layers separated. The aqueous layer was then extracted twice with chloroform, and the organic layers were combined and dried over MgSO4. The solvent was removed under reduced pressure, and the residue oil was purified by flash dry chromatography on silica using hexane/ethyl acetate (85:15) as the eluant. This resulted in the formation of colourless crystals. (5.30 g, 88%) ;