#------------------------------------------------------------------------------ #$Date: 2012-03-13 09:32:17 +0200 (Tue, 13 Mar 2012) $ #$Revision: 42312 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/47/1504718.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1504718 loop_ _publ_author_name 'Rudkin, Mairi E.' 'Joensuu, Pekka M.' 'MacLachlan, William S.' 'Lam, Hon Wai' _publ_section_title ; Diastereoselective cobalt-catalyzed alkylative aldol cyclizations using trialkylaluminum reagents. ; _journal_issue 14 _journal_name_full 'Organic letters' _journal_page_first 2939 _journal_page_last 2942 _journal_volume 10 _journal_year 2008 _chemical_compound_source ' MRA177A ' _chemical_formula_moiety 'C23 H29 N1 O2' _chemical_formula_sum 'C23 H29 N O2' _chemical_formula_weight 351.49 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 07-06-25 _audit_creation_method CRYSTALS_ver_12.84 _cell_angle_alpha 90 _cell_angle_beta 93.330(12) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 12.039(2) _cell_length_b 22.635(4) _cell_length_c 14.321(3) _cell_measurement_reflns_used 1924 _cell_measurement_temperature 150 _cell_measurement_theta_max 18 _cell_measurement_theta_min 2 _cell_volume 3895.9(12) _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_collection 'SMART (Siemens, 1993)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 150 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Bruker SMART' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.162 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 63706 _diffrn_reflns_theta_full 25.959 _diffrn_reflns_theta_max 26.489 _diffrn_reflns_theta_min 0.900 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_T_max 0.95 _exptl_absorpt_correction_T_min 0.72 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.198 _exptl_crystal_description plate _exptl_crystal_F_000 1520 _exptl_crystal_recrystallization_method ; Crystals dissolved in DCM in a small vial containing petroleum ether, sealed and left for a week. ; _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.34 _refine_diff_density_max 0.15 _refine_diff_density_min -0.14 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 1.0522 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 470 _refine_ls_number_reflns 4006 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1829 _refine_ls_R_factor_gt 0.0634 _refine_ls_shift/su_max 0.000155 _refine_ls_structure_factor_coef F _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 0.03P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1138 _refine_ls_wR_factor_gt 0.0671 _refine_ls_wR_factor_ref 0.0671 _reflns_limit_h_max 15 _reflns_limit_h_min -15 _reflns_limit_k_max 28 _reflns_limit_k_min 0 _reflns_limit_l_max 17 _reflns_limit_l_min 0 _reflns_number_gt 4006 _reflns_number_total 14735 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 1.87 _oxford_diffrn_Wilson_scale 186.98 _oxford_refine_ls_scale 0.3712(9) _oxford_structure_analysis_title 'hl7007 in P2(1)/c' _[local]_cod_data_source_file ol800883b-file005.cif _[local]_cod_data_source_block HL7007_cif _[local]_cod_cif_authors_sg_H-M 'P 1 21/c 1 ' _[local]_cod_chemical_formula_sum_orig 'C23 H29 N1 O2' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 1504718 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_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 C11 C -0.5450(4) 0.0732(2) 0.4417(3) 0.0396 1.0000 Uani C21 C -0.5081(4) 0.1327(2) 0.4058(3) 0.0331 1.0000 Uani C31 C -0.4056(4) 0.15704(19) 0.4634(3) 0.0263 1.0000 Uani C41 C -0.3056(4) 0.11764(19) 0.4536(3) 0.0288 1.0000 Uani C51 C -0.2691(4) 0.0795(2) 0.5246(3) 0.0354 1.0000 Uani C61 C -0.1798(4) 0.0422(2) 0.5135(4) 0.0440 1.0000 Uani C71 C -0.1252(4) 0.0426(2) 0.4316(4) 0.0464 1.0000 Uani C81 C -0.1595(4) 0.0812(2) 0.3604(4) 0.0402 1.0000 Uani C91 C -0.2493(4) 0.1175(2) 0.3714(3) 0.0330 1.0000 Uani C101 C -0.3782(3) 0.22381(19) 0.4426(3) 0.0243 1.0000 Uani C111 C -0.3944(4) 0.26487(19) 0.5263(3) 0.0263 1.0000 Uani O111 O -0.3429(2) 0.23637(13) 0.60615(18) 0.0323 1.0000 Uani C121 C -0.3364(4) 0.32357(19) 0.5112(3) 0.0287 1.0000 Uani C131 C -0.3428(4) 0.3677(2) 0.5903(3) 0.0434 1.0000 Uani C141 C -0.5183(4) 0.27171(18) 0.5354(3) 0.0279 1.0000 Uani C151 C -0.5749(4) 0.2987(2) 0.4487(3) 0.0306 1.0000 Uani N151 N -0.5370(3) 0.27385(16) 0.3615(2) 0.0268 1.0000 Uani C161 C -0.4411(4) 0.2439(2) 0.3544(3) 0.0270 1.0000 Uani O161 O -0.4066(3) 0.22990(13) 0.2776(2) 0.0351 1.0000 Uani C171 C -0.6074(4) 0.2865(2) 0.2775(3) 0.0338 1.0000 Uani C181 C -0.6124(4) 0.3517(2) 0.2550(3) 0.0304 1.0000 Uani C191 C -0.5177(4) 0.3820(2) 0.2317(3) 0.0422 1.0000 Uani C201 C -0.5227(5) 0.4420(2) 0.2126(4) 0.0500 1.0000 Uani C211 C -0.6213(5) 0.4716(2) 0.2151(4) 0.0505 1.0000 Uani C221 C -0.7142(5) 0.4423(3) 0.2376(4) 0.0615 1.0000 Uani C231 C -0.7100(4) 0.3825(2) 0.2586(3) 0.0475 1.0000 Uani C12 C -0.0430(4) 0.4284(2) 0.5641(4) 0.0437 1.0000 Uani C22 C 0.0020(4) 0.37069(19) 0.6061(3) 0.0317 1.0000 Uani C32 C 0.0972(4) 0.34529(19) 0.5516(3) 0.0268 1.0000 Uani C42 C 0.1980(4) 0.38473(19) 0.5613(3) 0.0283 1.0000 Uani C52 C 0.2247(4) 0.4227(2) 0.4900(3) 0.0378 1.0000 Uani C62 C 0.3162(4) 0.4590(2) 0.4980(4) 0.0433 1.0000 Uani C72 C 0.3827(4) 0.4593(2) 0.5799(4) 0.0445 1.0000 Uani C82 C 0.3577(4) 0.4222(2) 0.6522(4) 0.0392 1.0000 Uani C92 C 0.2665(4) 0.38563(19) 0.6429(3) 0.0312 1.0000 Uani C102 C 0.1275(4) 0.2797(2) 0.5751(3) 0.0269 1.0000 Uani C112 C 0.1059(3) 0.23738(18) 0.4908(3) 0.0243 1.0000 Uani O112 O 0.1516(2) 0.26624(13) 0.41340(19) 0.0333 1.0000 Uani C122 C 0.1670(4) 0.1791(2) 0.5110(3) 0.0310 1.0000 Uani C132 C 0.1531(4) 0.1329(2) 0.4339(3) 0.0437 1.0000 Uani C142 C -0.0192(4) 0.23032(18) 0.4759(3) 0.0279 1.0000 Uani C152 C -0.0693(4) 0.20275(19) 0.5605(3) 0.0291 1.0000 Uani N152 N -0.0225(3) 0.22708(16) 0.6492(2) 0.0287 1.0000 Uani C162 C 0.0707(4) 0.2588(2) 0.6606(3) 0.0296 1.0000 Uani O162 O 0.1099(2) 0.27571(13) 0.7385(2) 0.0346 1.0000 Uani C172 C -0.0901(4) 0.2165(2) 0.7293(3) 0.0341 1.0000 Uani C182 C -0.1075(4) 0.1522(2) 0.7512(3) 0.0284 1.0000 Uani C192 C -0.2069(4) 0.1356(2) 0.7854(3) 0.0396 1.0000 Uani C202 C -0.2250(4) 0.0765(2) 0.8087(4) 0.0519 1.0000 Uani C212 C -0.1448(5) 0.0353(2) 0.7981(4) 0.0499 1.0000 Uani C222 C -0.0457(4) 0.0514(2) 0.7638(4) 0.0483 1.0000 Uani C232 C -0.0266(4) 0.1098(2) 0.7414(3) 0.0397 1.0000 Uani H1011 H -0.2974 0.2253 0.4300 0.0295 1.0000 Uiso H1411 H -0.5311 0.2970 0.5897 0.0335 1.0000 Uiso H1412 H -0.5509 0.2321 0.5447 0.0335 1.0000 Uiso H1511 H -0.6561 0.2926 0.4508 0.0353 1.0000 Uiso H1512 H -0.5590 0.3420 0.4496 0.0353 1.0000 Uiso H1711 H -0.6843 0.2726 0.2881 0.0404 1.0000 Uiso H1712 H -0.5785 0.2650 0.2246 0.0404 1.0000 Uiso H1911 H -0.4492 0.3616 0.2283 0.0496 1.0000 Uiso H2011 H -0.4572 0.4624 0.1963 0.0601 1.0000 Uiso H2111 H -0.6248 0.5130 0.2020 0.0634 1.0000 Uiso H2211 H -0.7825 0.4628 0.2395 0.0750 1.0000 Uiso H2311 H -0.7757 0.3625 0.2748 0.0578 1.0000 Uiso H1211 H -0.3711 0.3416 0.4534 0.0346 1.0000 Uiso H1212 H -0.2568 0.3154 0.5018 0.0346 1.0000 Uiso H1311 H -0.3036 0.4039 0.5740 0.0518 1.0000 Uiso H1312 H -0.4207 0.3767 0.5996 0.0518 1.0000 Uiso H1313 H -0.3075 0.3508 0.6474 0.0518 1.0000 Uiso H311 H -0.4233 0.1551 0.5308 0.0319 1.0000 Uiso H511 H -0.3063 0.0787 0.5808 0.0446 1.0000 Uiso H611 H -0.1565 0.0161 0.5625 0.0521 1.0000 Uiso H711 H -0.0646 0.0165 0.4235 0.0561 1.0000 Uiso H811 H -0.1209 0.0827 0.3045 0.0480 1.0000 Uiso H911 H -0.2735 0.1431 0.3212 0.0398 1.0000 Uiso H211 H -0.5697 0.1611 0.4093 0.0387 1.0000 Uiso H212 H -0.4884 0.1281 0.3401 0.0387 1.0000 Uiso H111 H -0.6101 0.0595 0.4034 0.0497 1.0000 Uiso H112 H -0.5651 0.0772 0.5070 0.0497 1.0000 Uiso H113 H -0.4846 0.0445 0.4384 0.0497 1.0000 Uiso H1021 H 0.2096 0.2789 0.5919 0.0303 1.0000 Uiso H1421 H -0.0535 0.2695 0.4644 0.0334 1.0000 Uiso H1422 H -0.0361 0.2044 0.4210 0.0334 1.0000 Uiso H1521 H -0.1503 0.2100 0.5558 0.0353 1.0000 Uiso H1522 H -0.0547 0.1598 0.5594 0.0353 1.0000 Uiso H1721 H -0.0523 0.2352 0.7849 0.0402 1.0000 Uiso H1722 H -0.1635 0.2351 0.7160 0.0402 1.0000 Uiso H2321 H 0.0431 0.1207 0.7181 0.0479 1.0000 Uiso H2221 H 0.0098 0.0225 0.7553 0.0585 1.0000 Uiso H2121 H -0.1570 -0.0050 0.8147 0.0603 1.0000 Uiso H2021 H -0.2945 0.0651 0.8327 0.0597 1.0000 Uiso H1921 H -0.2635 0.1640 0.7941 0.0485 1.0000 Uiso H1221 H 0.1380 0.1620 0.5687 0.0371 1.0000 Uiso H1222 H 0.2471 0.1876 0.5218 0.0371 1.0000 Uiso H1321 H 0.1942 0.0972 0.4526 0.0504 1.0000 Uiso H1322 H 0.0739 0.1234 0.4227 0.0504 1.0000 Uiso H1323 H 0.1819 0.1487 0.3763 0.0504 1.0000 Uiso H321 H 0.0706 0.3461 0.4844 0.0332 1.0000 Uiso H921 H 0.2498 0.3607 0.6941 0.0351 1.0000 Uiso H821 H 0.4042 0.4219 0.7080 0.0474 1.0000 Uiso H721 H 0.4460 0.4845 0.5866 0.0529 1.0000 Uiso H621 H 0.3328 0.4842 0.4472 0.0533 1.0000 Uiso H521 H 0.1783 0.4231 0.4338 0.0471 1.0000 Uiso H221 H 0.0296 0.3780 0.6716 0.0382 1.0000 Uiso H222 H -0.0594 0.3415 0.6054 0.0382 1.0000 Uiso H121 H -0.1031 0.4431 0.6007 0.0504 1.0000 Uiso H122 H 0.0174 0.4577 0.5649 0.0504 1.0000 Uiso H123 H -0.0708 0.4216 0.4994 0.0504 1.0000 Uiso H1111 H -0.3627 0.2470 0.6602 0.0485 1.0000 Uiso H1121 H 0.1385 0.2530 0.3577 0.0499 1.0000 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C11 0.040(3) 0.037(3) 0.042(3) -0.003(2) 0.005(3) -0.003(3) C21 0.031(3) 0.031(3) 0.036(3) 0.003(2) 0.001(2) 0.000(2) C31 0.036(3) 0.024(3) 0.020(3) 0.001(2) 0.007(2) 0.005(2) C41 0.037(3) 0.021(3) 0.028(3) -0.006(2) 0.001(2) -0.006(2) C51 0.045(3) 0.028(3) 0.032(3) 0.002(2) -0.001(3) 0.000(3) C61 0.047(4) 0.032(3) 0.051(4) 0.006(3) -0.015(3) 0.004(3) C71 0.034(3) 0.039(3) 0.065(4) -0.016(3) -0.006(3) 0.005(3) C81 0.040(3) 0.036(3) 0.044(4) -0.009(3) 0.004(3) 0.001(3) C91 0.041(3) 0.030(3) 0.028(3) -0.004(2) -0.002(3) 0.004(3) C101 0.025(3) 0.025(3) 0.023(3) 0.000(2) 0.005(2) 0.000(2) C111 0.030(3) 0.031(3) 0.017(3) 0.006(2) -0.001(2) -0.004(2) O111 0.0409(19) 0.041(2) 0.0148(17) -0.0002(15) 0.0013(15) 0.0089(17) C121 0.027(3) 0.032(3) 0.027(3) -0.004(2) -0.001(2) 0.004(2) C131 0.044(3) 0.043(3) 0.043(3) -0.012(3) 0.005(3) -0.004(3) C141 0.035(3) 0.028(3) 0.022(3) 0.002(2) 0.006(2) -0.005(2) C151 0.033(3) 0.040(3) 0.019(3) 0.000(2) 0.004(2) 0.003(2) N151 0.029(2) 0.031(2) 0.020(2) 0.0024(18) -0.0023(18) 0.003(2) C161 0.033(3) 0.025(3) 0.022(3) 0.003(2) 0.000(2) -0.008(2) O161 0.049(2) 0.039(2) 0.0175(18) -0.0003(16) 0.0104(16) 0.0061(17) C171 0.038(3) 0.036(3) 0.027(3) 0.005(2) -0.003(2) -0.003(2) C181 0.032(3) 0.043(3) 0.016(3) 0.005(2) -0.001(2) 0.008(3) C191 0.031(3) 0.049(4) 0.047(4) 0.002(3) 0.006(3) 0.007(3) C201 0.052(4) 0.040(4) 0.059(4) 0.013(3) 0.009(3) 0.000(3) C211 0.062(4) 0.045(4) 0.046(4) 0.015(3) 0.013(3) 0.016(3) C221 0.052(4) 0.065(4) 0.069(5) 0.028(4) 0.016(3) 0.024(3) C231 0.031(3) 0.066(4) 0.046(4) 0.016(3) 0.002(3) 0.005(3) C12 0.045(3) 0.033(3) 0.053(4) 0.003(3) -0.002(3) -0.001(3) C22 0.028(3) 0.027(3) 0.040(3) 0.003(2) -0.002(2) -0.005(2) C32 0.031(3) 0.028(3) 0.020(3) 0.003(2) -0.005(2) -0.004(2) C42 0.031(3) 0.027(3) 0.027(3) -0.002(2) 0.003(2) 0.002(2) C52 0.047(3) 0.036(3) 0.030(3) 0.006(3) 0.006(3) -0.002(3) C62 0.047(4) 0.030(3) 0.054(4) 0.011(3) 0.012(3) -0.006(3) C72 0.036(3) 0.031(3) 0.067(4) -0.011(3) 0.009(3) 0.001(3) C82 0.037(3) 0.038(3) 0.042(4) -0.004(3) -0.003(3) 0.003(3) C92 0.035(3) 0.027(3) 0.032(3) 0.000(2) 0.006(3) -0.001(3) C102 0.027(3) 0.032(3) 0.021(3) 0.002(2) -0.005(2) -0.004(2) C112 0.027(3) 0.026(3) 0.019(3) 0.003(2) -0.002(2) -0.003(2) O112 0.043(2) 0.040(2) 0.0174(19) -0.0003(15) 0.0043(15) -0.0097(17) C122 0.026(3) 0.037(3) 0.030(3) -0.005(2) 0.001(2) 0.001(2) C132 0.048(3) 0.035(3) 0.049(4) -0.006(3) 0.006(3) 0.002(3) C142 0.033(3) 0.030(3) 0.021(3) -0.005(2) 0.001(2) -0.002(2) C152 0.029(3) 0.032(3) 0.026(3) -0.002(2) 0.002(2) -0.001(2) N152 0.033(3) 0.031(2) 0.022(2) -0.0006(19) -0.0001(19) -0.003(2) C162 0.030(3) 0.026(3) 0.033(3) 0.003(2) -0.001(2) 0.004(2) O162 0.041(2) 0.044(2) 0.0177(19) -0.0020(16) -0.0048(16) -0.0051(16) C172 0.034(3) 0.044(3) 0.025(3) -0.002(2) 0.001(2) -0.004(3) C182 0.027(3) 0.042(3) 0.016(3) 0.001(2) -0.004(2) -0.002(3) C192 0.040(3) 0.045(3) 0.033(3) 0.006(3) 0.004(3) 0.002(3) C202 0.040(4) 0.059(4) 0.057(4) 0.020(3) 0.004(3) -0.007(3) C212 0.053(4) 0.044(4) 0.053(4) 0.019(3) 0.001(3) -0.004(3) C222 0.042(4) 0.044(4) 0.059(4) 0.016(3) 0.003(3) 0.004(3) C232 0.029(3) 0.052(4) 0.038(3) 0.008(3) 0.003(3) 0.000(3) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C21 C11 H111 109.4 no C21 C11 H112 109.5 no H111 C11 H112 109.2 no C21 C11 H113 109.9 no H111 C11 H113 109.5 no H112 C11 H113 109.3 no C11 C21 C31 112.1(4) yes C11 C21 H211 109.0 no C31 C21 H211 108.6 no C11 C21 H212 108.6 no C31 C21 H212 108.5 no H211 C21 H212 110.0 no C21 C31 C41 110.8(3) yes C21 C31 C101 114.2(3) yes C41 C31 C101 111.8(4) yes C21 C31 H311 106.9 no C41 C31 H311 106.2 no C101 C31 H311 106.5 no C31 C41 C51 121.3(4) yes C31 C41 C91 120.6(4) yes C51 C41 C91 118.1(4) yes C41 C51 C61 120.7(4) yes C41 C51 H511 119.5 no C61 C51 H511 119.7 no C51 C61 C71 120.4(5) yes C51 C61 H611 119.6 no C71 C61 H611 120.1 no C61 C71 C81 119.7(5) yes C61 C71 H711 120.4 no C81 C71 H711 120.0 no C71 C81 C91 119.6(5) yes C71 C81 H811 120.2 no C91 C81 H811 120.2 no C41 C91 C81 121.5(5) yes C41 C91 H911 119.6 no C81 C91 H911 118.8 no C31 C101 C111 113.2(3) yes C31 C101 C161 110.4(3) yes C111 C101 C161 113.1(4) yes C31 C101 H1011 106.4 no C111 C101 H1011 106.7 no C161 C101 H1011 106.6 no C101 C111 O111 106.5(3) yes C101 C111 C121 109.6(3) yes O111 C111 C121 109.1(3) yes C101 C111 C141 107.4(3) yes O111 C111 C141 111.3(3) yes C121 C111 C141 112.7(4) yes C111 O111 H1111 117.8 no C111 C121 C131 115.1(4) yes C111 C121 H1211 107.6 no C131 C121 H1211 108.4 no C111 C121 H1212 108.2 no C131 C121 H1212 108.4 no H1211 C121 H1212 109.1 no C121 C131 H1311 109.1 no C121 C131 H1312 109.3 no H1311 C131 H1312 109.7 no C121 C131 H1313 109.2 no H1311 C131 H1313 109.5 no H1312 C131 H1313 110.0 no C111 C141 C151 111.8(3) yes C111 C141 H1411 109.1 no C151 C141 H1411 109.3 no C111 C141 H1412 108.6 no C151 C141 H1412 108.3 no H1411 C141 H1412 109.8 no C141 C151 N151 113.4(4) yes C141 C151 H1511 108.5 no N151 C151 H1511 109.3 no C141 C151 H1512 107.9 no N151 C151 H1512 108.6 no H1511 C151 H1512 109.0 no C151 N151 C161 124.6(4) yes C151 N151 C171 115.6(3) yes C161 N151 C171 119.8(4) yes C101 C161 N151 118.7(4) yes C101 C161 O161 119.3(4) yes N151 C161 O161 121.9(4) yes N151 C171 C181 112.5(4) yes N151 C171 H1711 108.2 no C181 C171 H1711 108.5 no N151 C171 H1712 108.8 no C181 C171 H1712 109.4 no H1711 C171 H1712 109.4 no C171 C181 C191 120.8(4) yes C171 C181 C231 120.7(4) yes C191 C181 C231 118.5(5) yes C181 C191 C201 120.4(5) yes C181 C191 H1911 120.0 no C201 C191 H1911 119.6 no C191 C201 C211 120.2(5) yes C191 C201 H2011 119.8 no C211 C201 H2011 120.0 no C201 C211 C221 119.7(5) yes C201 C211 H2111 120.3 no C221 C211 H2111 120.0 no C211 C221 C231 120.7(5) yes C211 C221 H2211 119.8 no C231 C221 H2211 119.6 no C221 C231 C181 120.5(5) yes C221 C231 H2311 119.9 no C181 C231 H2311 119.6 no C22 C12 H121 109.7 no C22 C12 H122 109.1 no H121 C12 H122 109.6 no C22 C12 H123 109.4 no H121 C12 H123 109.9 no H122 C12 H123 109.2 no C12 C22 C32 112.3(4) yes C12 C22 H221 108.8 no C32 C22 H221 108.9 no C12 C22 H222 108.7 no C32 C22 H222 108.8 no H221 C22 H222 109.3 no C22 C32 C42 110.6(4) yes C22 C32 C102 114.7(4) yes C42 C32 C102 111.5(4) yes C22 C32 H321 106.1 no C42 C32 H321 106.9 no C102 C32 H321 106.5 no C32 C42 C52 121.2(4) yes C32 C42 C92 121.5(4) yes C52 C42 C92 117.3(4) yes C42 C52 C62 121.8(4) yes C42 C52 H521 118.6 no C62 C52 H521 119.5 no C52 C62 C72 119.8(5) yes C52 C62 H621 119.8 no C72 C62 H621 120.5 no C62 C72 C82 119.6(5) yes C62 C72 H721 120.6 no C82 C72 H721 119.8 no C72 C82 C92 120.0(5) yes C72 C82 H821 119.6 no C92 C82 H821 120.4 no C42 C92 C82 121.4(4) yes C42 C92 H921 119.6 no C82 C92 H921 118.9 no C32 C102 C112 113.1(3) yes C32 C102 C162 111.2(4) yes C112 C102 C162 111.9(4) yes C32 C102 H1021 106.5 no C112 C102 H1021 107.1 no C162 C102 H1021 106.6 no C102 C112 O112 105.5(3) yes C102 C112 C122 109.1(3) yes O112 C112 C122 109.9(3) yes C102 C112 C142 107.1(3) yes O112 C112 C142 111.4(3) yes C122 C112 C142 113.5(3) yes C112 O112 H1121 120.3 no C112 C122 C132 115.1(4) yes C112 C122 H1221 107.8 no C132 C122 H1221 107.7 no C112 C122 H1222 108.5 no C132 C122 H1222 108.1 no H1221 C122 H1222 109.4 no C122 C132 H1321 109.8 no C122 C132 H1322 109.5 no H1321 C132 H1322 109.6 no C122 C132 H1323 109.2 no H1321 C132 H1323 109.6 no H1322 C132 H1323 109.2 no C112 C142 C152 111.6(4) yes C112 C142 H1421 109.4 no C152 C142 H1421 108.7 no C112 C142 H1422 109.2 no C152 C142 H1422 108.4 no H1421 C142 H1422 109.4 no C142 C152 N152 112.7(4) yes C142 C152 H1521 108.3 no N152 C152 H1521 108.9 no C142 C152 H1522 108.2 no N152 C152 H1522 108.9 no H1521 C152 H1522 109.8 no C152 N152 C162 125.9(4) yes C152 N152 C172 114.5(4) yes C162 N152 C172 119.6(4) yes C102 C162 N152 119.1(4) yes C102 C162 O162 117.6(4) yes N152 C162 O162 123.2(4) yes N152 C172 C182 114.3(4) yes N152 C172 H1721 108.0 no C182 C172 H1721 108.0 no N152 C172 H1722 108.2 no C182 C172 H1722 108.6 no H1721 C172 H1722 109.7 no C172 C182 C192 118.3(4) yes C172 C182 C232 122.9(4) yes C192 C182 C232 118.8(4) yes C182 C192 C202 120.0(5) yes C182 C192 H1921 120.5 no C202 C192 H1921 119.5 no C192 C202 C212 120.6(5) yes C192 C202 H2021 119.7 no C212 C202 H2021 119.7 no C202 C212 C222 119.9(5) yes C202 C212 H2121 120.5 no C222 C212 H2121 119.6 no C212 C222 C232 120.0(5) yes C212 C222 H2221 120.0 no C232 C222 H2221 120.0 no C222 C232 C182 120.8(5) yes C222 C232 H2321 119.3 no C182 C232 H2321 119.8 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C11 C21 1.516(6) yes C11 H111 0.980 no C11 H112 0.983 no C11 H113 0.979 no C21 C31 1.545(6) yes C21 H211 0.986 no C21 H212 0.988 no C31 C41 1.512(6) yes C31 C101 1.579(6) yes C31 H311 1.001 no C41 C51 1.386(6) yes C41 C91 1.391(6) yes C51 C61 1.384(7) yes C51 H511 0.943 no C61 C71 1.378(7) yes C61 H611 0.947 no C71 C81 1.386(7) yes C71 H711 0.952 no C81 C91 1.376(6) yes C81 H811 0.950 no C91 H911 0.954 no C101 C111 1.539(6) yes C101 C161 1.505(6) yes C101 H1011 1.000 no C111 O111 1.423(5) yes C111 C121 1.523(6) yes C111 C141 1.512(6) yes O111 H1111 0.858 no C121 C131 1.515(6) yes C121 H1211 0.992 no C121 H1212 0.993 no C131 H1311 0.982 no C131 H1312 0.976 no C131 H1313 0.978 no C141 C151 1.511(6) yes C141 H1411 0.985 no C141 H1412 0.992 no C151 N151 1.466(5) yes C151 H1511 0.989 no C151 H1512 0.998 no N151 C161 1.348(5) yes N151 C171 1.459(5) yes C161 O161 1.238(5) yes C171 C181 1.511(6) yes C171 H1711 0.998 no C171 H1712 0.983 no C181 C191 1.387(6) yes C181 C231 1.370(6) yes C191 C201 1.385(7) yes C191 H1911 0.950 no C201 C211 1.367(7) yes C201 H2011 0.954 no C211 C221 1.355(7) yes C211 H2111 0.955 no C221 C231 1.387(7) yes C221 H2211 0.946 no C231 H2311 0.951 no C12 C22 1.525(6) yes C12 H121 0.976 no C12 H122 0.983 no C12 H123 0.980 no C22 C32 1.536(6) yes C22 H221 0.991 no C22 H222 0.991 no C32 C42 1.507(6) yes C32 C102 1.561(6) yes C32 H321 0.996 no C42 C52 1.387(6) yes C42 C92 1.390(6) yes C52 C62 1.374(6) yes C52 H521 0.952 no C62 C72 1.381(7) yes C62 H621 0.955 no C72 C82 1.379(7) yes C72 H721 0.953 no C82 C92 1.376(6) yes C82 H821 0.948 no C92 H921 0.956 no C102 C112 1.552(6) yes C102 C162 1.513(6) yes C102 H1021 1.004 no C112 O112 1.424(5) yes C112 C122 1.530(6) yes C112 C142 1.517(6) yes O112 H1121 0.858 no C122 C132 1.523(6) yes C122 H1221 0.994 no C122 H1222 0.987 no C132 H1321 0.976 no C132 H1322 0.982 no C132 H1323 0.982 no C142 C152 1.518(6) yes C142 H1421 0.988 no C142 H1422 0.993 no C152 N152 1.466(5) yes C152 H1521 0.988 no C152 H1522 0.988 no N152 C162 1.334(5) yes N152 C172 1.464(5) yes C162 O162 1.246(5) yes C172 C182 1.506(6) yes C172 H1721 0.989 no C172 H1722 0.988 no C182 C192 1.372(6) yes C182 C232 1.380(6) yes C192 C202 1.397(7) yes C192 H1921 0.951 no C202 C212 1.358(7) yes C202 H2021 0.958 no C212 C222 1.365(7) yes C212 H2121 0.955 no C222 C232 1.385(7) yes C222 H2221 0.947 no C232 H2321 0.952 no loop_ _oxford_twin_element_scale_factors 0.531(2) 0.469(2)