#------------------------------------------------------------------------------ #$Date: 2021-03-05 04:30:27 +0200 (Fri, 05 Mar 2021) $ #$Revision: 262731 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/08/1560815.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_1560815 loop_ _publ_author_name 'MARFO-OWUSU, Emmanuel' 'THOMPSON, Amber L.' _publ_section_title ; The Crystal Structure of a Benzyltriethylammonium Bromide Complex with <i>rac</i>-1,1′-Binaphthalene-2,2′-diol: The Inclusion of an Arylammonium Salt by an Assembly of Binaphthol Groups ; _journal_issue 0 _journal_name_full 'X-ray Structure Analysis Online' _journal_page_first 7 _journal_page_last 8 _journal_paper_doi 10.2116/xraystruct.37.7 _journal_volume 37 _journal_year 2021 _chemical_formula_moiety 'C33 H36 Br1 N1 O2' _chemical_formula_sum 'C33 H36 Br N O2' _chemical_formula_weight 558.56 _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary other _audit_creation_date 2016-07-14 _audit_creation_method CRYSTALS_ver_14.43 _cell_angle_alpha 90 _cell_angle_beta 98.2242(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.81090(10) _cell_length_b 10.30810(10) _cell_length_c 25.2697(3) _cell_measurement_reflns_used 6656 _cell_measurement_temperature 0 _cell_measurement_theta_max 27 _cell_measurement_theta_min 5 _cell_volume 2787.09(5) _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _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 'Superflip (Palatinus & Chapuis, 2007)' _diffrn_ambient_temperature 150 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device Area _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.016 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 12248 _diffrn_reflns_theta_full 26.931 _diffrn_reflns_theta_max 27.481 _diffrn_reflns_theta_min 5.126 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.505 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_correction_T_min 0.57 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_crystal_colour colorlss _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_description rodlike _exptl_crystal_F_000 1168 _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.25 _refine_diff_density_max 0.44 _refine_diff_density_min -0.39 _refine_ls_extinction_coef 56(16) _refine_ls_extinction_method 'Larson (1970), Equation 22' _refine_ls_goodness_of_fit_ref 0.9840 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 335 _refine_ls_number_reflns 6333 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0326 _refine_ls_R_factor_gt 0.0283 _refine_ls_shift/su_max 0.0017436 _refine_ls_shift/su_mean 0.0000518 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.02P)^2^ + 2.11P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0656 _refine_ls_wR_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.0656 _reflns_limit_h_max 13 _reflns_limit_h_min -14 _reflns_limit_k_max 13 _reflns_limit_k_min 0 _reflns_limit_l_max 32 _reflns_limit_l_min 0 _reflns_number_gt 5729 _reflns_number_total 6333 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _oxford_refine_ls_r_factor_ref 0.0326 _oxford_refine_ls_scale 0.4706(5) _oxford_reflns_number_all 6333 _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _oxford_structure_analysis_title BTEAB/BNP _cod_data_source_file 37_7_1.txt _cod_data_source_block BTEAB/BNP _cod_depositor_comments ; The following automatic conversions were performed: data item '_atom_sites_solution_primary' value 'Other' was changed to 'other' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/current/J-STAGE/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_original_sg_symbol_H-M 'P 21/n ' _cod_original_formula_sum 'C33 H36 Br1 N1 O2' _cod_database_code 1560815 _iucr_refine_instructions_details_constraints ; # # Punched on 14/07/16 at 07:57:11 # #LIST 12 BLOCK SCALE X'S, U'S CONT EXTPARAM RIDE O ( 3,X'S) H ( 31,X'S) RIDE C ( 5,X'S) H ( 51,X'S) RIDE C ( 6,X'S) H ( 61,X'S) RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 10,X'S) H ( 101,X'S) RIDE C ( 11,X'S) H ( 111,X'S) RIDE O ( 16,X'S) H ( 161,X'S) RIDE C ( 17,X'S) H ( 171,X'S) RIDE C ( 18,X'S) H ( 181,X'S) RIDE C ( 21,X'S) H ( 211,X'S) RIDE C ( 22,X'S) H ( 221,X'S) RIDE C ( 23,X'S) H ( 231,X'S) RIDE C ( 24,X'S) H ( 241,X'S) RIDE C ( 26,X'S) H ( 261,X'S) H ( 262,X'S) RIDE C ( 27,X'S) H ( 271,X'S) H ( 272,X'S) H ( 273,X'S) RIDE C ( 28,X'S) H ( 281,X'S) H ( 282,X'S) RIDE C ( 29,X'S) H ( 291,X'S) H ( 292,X'S) H ( 293,X'S) RIDE C ( 30,X'S) H ( 301,X'S) H ( 302,X'S) RIDE C ( 31,X'S) H ( 311,X'S) H ( 313,X'S) H ( 312,X'S) RIDE C ( 32,X'S) H ( 321,X'S) H ( 322,X'S) RIDE C ( 34,X'S) H ( 341,X'S) RIDE C ( 35,X'S) H ( 351,X'S) RIDE C ( 36,X'S) H ( 361,X'S) RIDE C ( 37,X'S) H ( 371,X'S) RIDE C ( 38,X'S) H ( 381,X'S) END ; loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,-y+1/2,z+1/2 -x+1/2,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 _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Br1 Br 0.253083(13) 0.234050(14) 0.481587(6) 0.0229 1.0000 Uani . . . . . . O3 O 0.12652(11) 0.18864(11) 0.58878(5) 0.0312 1.0000 Uani . . . . . . C4 C 0.03518(14) 0.27039(14) 0.60043(6) 0.0213 1.0000 Uani . . . . . . C5 C 0.01752(14) 0.39332(15) 0.57551(6) 0.0250 1.0000 Uani . . . . . . C6 C -0.07322(14) 0.47539(15) 0.58811(6) 0.0251 1.0000 Uani . . . . . . C7 C -0.15167(14) 0.43851(15) 0.62597(6) 0.0232 1.0000 Uani . . . . . . C8 C -0.24862(15) 0.52089(17) 0.63899(7) 0.0299 1.0000 Uani . . . . . . C9 C -0.32549(16) 0.48156(18) 0.67432(7) 0.0342 1.0000 Uani . . . . . . C10 C -0.30969(16) 0.35826(18) 0.69825(7) 0.0327 1.0000 Uani . . . . . . C11 C -0.21638(15) 0.27675(16) 0.68718(6) 0.0261 1.0000 Uani . . . . . . C12 C -0.13460(13) 0.31414(15) 0.65065(6) 0.0206 1.0000 Uani . . . . . . C13 C -0.03843(13) 0.22992(14) 0.63763(6) 0.0194 1.0000 Uani . . . . . . C14 C -0.01846(13) 0.09821(14) 0.66229(6) 0.0203 1.0000 Uani . . . . . . C15 C -0.07161(14) -0.00931(15) 0.63586(6) 0.0222 1.0000 Uani . . . . . . O16 O -0.14618(10) 0.00952(11) 0.58822(4) 0.0280 1.0000 Uani . . . . . . C17 C -0.04990(15) -0.13590(15) 0.65701(6) 0.0254 1.0000 Uani . . . . . . C18 C 0.02523(15) -0.15343(16) 0.70457(6) 0.0270 1.0000 Uani . . . . . . C19 C 0.08097(14) -0.04634(16) 0.73408(6) 0.0245 1.0000 Uani . . . . . . C20 C 0.05810(13) 0.08094(15) 0.71274(6) 0.0212 1.0000 Uani . . . . . . C21 C 0.11322(14) 0.18749(16) 0.74283(6) 0.0254 1.0000 Uani . . . . . . C22 C 0.18807(16) 0.16873(18) 0.79073(6) 0.0315 1.0000 Uani . . . . . . C23 C 0.21200(17) 0.04272(19) 0.81123(7) 0.0352 1.0000 Uani . . . . . . C24 C 0.15905(16) -0.06229(18) 0.78390(6) 0.0311 1.0000 Uani . . . . . . N25 N 0.32919(11) -0.22008(12) 0.53741(5) 0.0201 1.0000 Uani . . . . . . C26 C 0.20550(14) -0.22591(16) 0.55949(6) 0.0266 1.0000 Uani . . . . . . C27 C 0.10737(15) -0.12943(19) 0.53590(7) 0.0346 1.0000 Uani . . . . . . C28 C 0.30251(15) -0.23841(16) 0.47702(6) 0.0250 1.0000 Uani . . . . . . C29 C 0.41606(16) -0.24226(18) 0.44850(7) 0.0307 1.0000 Uani . . . . . . C30 C 0.41492(15) -0.32491(15) 0.56407(6) 0.0252 1.0000 Uani . . . . . . C31 C 0.37447(19) -0.46289(17) 0.55000(8) 0.0382 1.0000 Uani . . . . . . C32 C 0.39350(15) -0.08851(15) 0.54935(6) 0.0241 1.0000 Uani . . . . . . C33 C 0.43572(14) -0.06014(14) 0.60768(6) 0.0230 1.0000 Uani . . . . . . C34 C 0.35717(15) -0.00229(15) 0.63977(7) 0.0279 1.0000 Uani . . . . . . C35 C 0.40096(17) 0.02649(17) 0.69297(7) 0.0319 1.0000 Uani . . . . . . C36 C 0.52338(17) -0.00100(17) 0.71432(7) 0.0326 1.0000 Uani . . . . . . C37 C 0.60256(16) -0.05607(19) 0.68233(7) 0.0347 1.0000 Uani . . . . . . C38 C 0.55931(15) -0.08556(17) 0.62938(7) 0.0295 1.0000 Uani . . . . . . H51 H 0.0697 0.4183 0.5491 0.0323 1.0000 Uiso R . . . . . H61 H -0.0838 0.5598 0.5713 0.0309 1.0000 Uiso R . . . . . H81 H -0.2591 0.6061 0.6217 0.0362 1.0000 Uiso R . . . . . H91 H -0.3922 0.5384 0.6824 0.0410 1.0000 Uiso R . . . . . H101 H -0.3638 0.3306 0.7232 0.0396 1.0000 Uiso R . . . . . H111 H -0.2069 0.1918 0.7036 0.0322 1.0000 Uiso R . . . . . H171 H -0.0896 -0.2083 0.6372 0.0312 1.0000 Uiso R . . . . . H181 H 0.0403 -0.2389 0.7192 0.0329 1.0000 Uiso R . . . . . H211 H 0.0972 0.2743 0.7301 0.0312 1.0000 Uiso R . . . . . H221 H 0.2239 0.2428 0.8108 0.0386 1.0000 Uiso R . . . . . H231 H 0.2661 0.0314 0.8451 0.0418 1.0000 Uiso R . . . . . H241 H 0.1741 -0.1484 0.7973 0.0368 1.0000 Uiso R . . . . . H261 H 0.2272 -0.2121 0.5989 0.0329 1.0000 Uiso R . . . . . H262 H 0.1746 -0.3159 0.5521 0.0345 1.0000 Uiso R . . . . . H271 H 0.0340 -0.1421 0.5529 0.0540 1.0000 Uiso R . . . . . H272 H 0.1353 -0.0407 0.5408 0.0539 1.0000 Uiso R . . . . . H273 H 0.0848 -0.1440 0.4977 0.0525 1.0000 Uiso R . . . . . H281 H 0.2569 -0.3216 0.4729 0.0316 1.0000 Uiso R . . . . . H282 H 0.2496 -0.1647 0.4636 0.0319 1.0000 Uiso R . . . . . H291 H 0.3911 -0.2715 0.4114 0.0474 1.0000 Uiso R . . . . . H292 H 0.4785 -0.3017 0.4689 0.0484 1.0000 Uiso R . . . . . H293 H 0.4515 -0.1559 0.4486 0.0498 1.0000 Uiso R . . . . . H301 H 0.4176 -0.3118 0.6033 0.0304 1.0000 Uiso R . . . . . H302 H 0.4978 -0.3088 0.5533 0.0315 1.0000 Uiso R . . . . . H311 H 0.4323 -0.5199 0.5731 0.0595 1.0000 Uiso R . . . . . H313 H 0.2905 -0.4767 0.5590 0.0598 1.0000 Uiso R . . . . . H312 H 0.3760 -0.4814 0.5114 0.0585 1.0000 Uiso R . . . . . H321 H 0.4670 -0.0929 0.5295 0.0293 1.0000 Uiso R . . . . . H322 H 0.3342 -0.0212 0.5321 0.0295 1.0000 Uiso R . . . . . H341 H 0.2718 0.0192 0.6249 0.0334 1.0000 Uiso R . . . . . H351 H 0.3460 0.0662 0.7157 0.0378 1.0000 Uiso R . . . . . H361 H 0.5529 0.0189 0.7516 0.0402 1.0000 Uiso R . . . . . H371 H 0.6887 -0.0751 0.6965 0.0417 1.0000 Uiso R . . . . . H381 H 0.6145 -0.1239 0.6072 0.0365 1.0000 Uiso R . . . . . H31 H 0.1616 0.2152 0.5646 0.0489 1.0000 Uiso R . . . . . H161 H -0.1723 -0.0648 0.5743 0.0439 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 Br1 0.02232(9) 0.02349(9) 0.02309(9) -0.00122(6) 0.00355(6) -0.00124(6) O3 0.0309(6) 0.0306(6) 0.0357(6) 0.0096(5) 0.0169(5) 0.0108(5) C4 0.0193(7) 0.0229(7) 0.0219(7) -0.0004(6) 0.0032(6) 0.0014(6) C5 0.0234(7) 0.0250(8) 0.0269(8) 0.0045(6) 0.0043(6) -0.0020(6) C6 0.0268(8) 0.0205(7) 0.0270(8) 0.0030(6) 0.0006(6) 0.0000(6) C7 0.0232(7) 0.0228(7) 0.0226(7) -0.0027(6) -0.0004(6) 0.0011(6) C8 0.0308(8) 0.0274(8) 0.0307(8) -0.0023(7) 0.0016(7) 0.0061(7) C9 0.0296(9) 0.0384(10) 0.0348(9) -0.0057(7) 0.0051(7) 0.0108(7) C10 0.0285(8) 0.0434(10) 0.0276(8) -0.0015(7) 0.0091(7) 0.0033(7) C11 0.0262(8) 0.0292(8) 0.0233(7) -0.0004(6) 0.0050(6) 0.0011(6) C12 0.0206(7) 0.0224(7) 0.0182(7) -0.0026(6) 0.0006(5) -0.0006(6) C13 0.0199(7) 0.0201(7) 0.0175(7) -0.0016(5) 0.0007(5) -0.0013(5) C14 0.0205(7) 0.0208(7) 0.0204(7) 0.0016(6) 0.0058(5) 0.0009(6) C15 0.0203(7) 0.0244(8) 0.0224(7) 0.0004(6) 0.0044(6) 0.0007(6) O16 0.0312(6) 0.0237(6) 0.0267(6) -0.0024(4) -0.0046(5) -0.0017(5) C17 0.0275(8) 0.0211(7) 0.0285(8) -0.0012(6) 0.0073(6) -0.0023(6) C18 0.0299(8) 0.0226(8) 0.0302(8) 0.0054(6) 0.0103(7) 0.0031(6) C19 0.0243(7) 0.0284(8) 0.0221(7) 0.0042(6) 0.0076(6) 0.0041(6) C20 0.0203(7) 0.0243(7) 0.0202(7) 0.0001(6) 0.0069(6) 0.0007(6) C21 0.0268(8) 0.0278(8) 0.0221(7) -0.0019(6) 0.0055(6) -0.0001(6) C22 0.0324(9) 0.0393(10) 0.0223(8) -0.0064(7) 0.0022(6) 0.0002(7) C23 0.0353(9) 0.0496(11) 0.0197(8) 0.0016(7) 0.0003(7) 0.0079(8) C24 0.0338(9) 0.0353(9) 0.0248(8) 0.0069(7) 0.0064(7) 0.0086(7) N25 0.0190(6) 0.0219(6) 0.0188(6) 0.0002(5) 0.0011(5) 0.0006(5) C26 0.0215(7) 0.0343(9) 0.0248(8) -0.0009(6) 0.0061(6) -0.0010(6) C27 0.0233(8) 0.0487(11) 0.0320(9) -0.0056(8) 0.0043(7) 0.0073(7) C28 0.0217(7) 0.0348(9) 0.0175(7) -0.0021(6) -0.0006(6) 0.0012(6) C29 0.0255(8) 0.0439(10) 0.0227(8) -0.0059(7) 0.0034(6) 0.0019(7) C30 0.0268(8) 0.0206(8) 0.0271(8) 0.0024(6) -0.0002(6) 0.0039(6) C31 0.0478(11) 0.0229(9) 0.0441(10) -0.0029(8) 0.0069(8) 0.0024(8) C32 0.0294(8) 0.0206(7) 0.0220(7) 0.0017(6) 0.0024(6) -0.0021(6) C33 0.0276(8) 0.0187(7) 0.0228(7) -0.0008(6) 0.0038(6) -0.0027(6) C34 0.0288(8) 0.0229(8) 0.0312(8) -0.0031(6) 0.0019(7) 0.0044(6) C35 0.0371(9) 0.0303(9) 0.0293(8) -0.0080(7) 0.0083(7) 0.0002(7) C36 0.0391(9) 0.0349(9) 0.0230(8) -0.0055(7) 0.0019(7) -0.0057(7) C37 0.0266(8) 0.0434(10) 0.0326(9) -0.0063(8) -0.0013(7) -0.0018(7) C38 0.0244(8) 0.0360(9) 0.0286(8) -0.0065(7) 0.0052(6) -0.0023(7) 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' 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' Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328 2.9557 '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' 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 C4 . O3 . H31 . 112.7 no O3 . C4 . C5 . 120.89(13) yes O3 . C4 . C13 . 117.83(13) yes C5 . C4 . C13 . 121.28(14) yes C4 . C5 . C6 . 120.40(14) yes C4 . C5 . H51 . 119.3 no C6 . C5 . H51 . 120.3 no C5 . C6 . C7 . 120.63(14) yes C5 . C6 . H61 . 119.9 no C7 . C6 . H61 . 119.5 no C6 . C7 . C8 . 121.81(15) yes C6 . C7 . C12 . 118.93(14) yes C8 . C7 . C12 . 119.25(14) yes C7 . C8 . C9 . 120.74(16) yes C7 . C8 . H81 . 118.2 no C9 . C8 . H81 . 121.0 no C8 . C9 . C10 . 120.08(16) yes C8 . C9 . H91 . 119.8 no C10 . C9 . H91 . 120.1 no C9 . C10 . C11 . 120.86(16) yes C9 . C10 . H101 . 120.1 no C11 . C10 . H101 . 119.1 no C10 . C11 . C12 . 120.72(15) yes C10 . C11 . H111 . 120.2 no C12 . C11 . H111 . 119.1 no C7 . C12 . C11 . 118.35(14) yes C7 . C12 . C13 . 119.89(13) yes C11 . C12 . C13 . 121.75(14) yes C12 . C13 . C4 . 118.87(13) yes C12 . C13 . C14 . 121.45(13) yes C4 . C13 . C14 . 119.67(13) yes C13 . C14 . C15 . 120.19(13) yes C13 . C14 . C20 . 121.03(13) yes C15 . C14 . C20 . 118.76(13) yes C14 . C15 . O16 . 117.83(13) yes C14 . C15 . C17 . 121.55(14) yes O16 . C15 . C17 . 120.62(14) yes C15 . O16 . H161 . 110.3 no C15 . C17 . C18 . 120.03(15) yes C15 . C17 . H171 . 118.7 no C18 . C17 . H171 . 121.3 no C17 . C18 . C19 . 121.03(14) yes C17 . C18 . H181 . 120.5 no C19 . C18 . H181 . 118.4 no C18 . C19 . C20 . 118.67(14) yes C18 . C19 . C24 . 121.99(15) yes C20 . C19 . C24 . 119.34(15) yes C14 . C20 . C19 . 119.93(14) yes C14 . C20 . C21 . 121.85(14) yes C19 . C20 . C21 . 118.22(14) yes C20 . C21 . C22 . 120.95(15) yes C20 . C21 . H211 . 120.1 no C22 . C21 . H211 . 118.9 no C21 . C22 . C23 . 120.61(16) yes C21 . C22 . H221 . 119.5 no C23 . C22 . H221 . 119.8 no C22 . C23 . C24 . 120.24(15) yes C22 . C23 . H231 . 119.4 no C24 . C23 . H231 . 120.4 no C19 . C24 . C23 . 120.61(16) yes C19 . C24 . H241 . 118.0 no C23 . C24 . H241 . 121.4 no C26 . N25 . C28 . 108.18(11) yes C26 . N25 . C30 . 108.78(12) yes C28 . N25 . C30 . 111.88(12) yes C26 . N25 . C32 . 111.10(12) yes C28 . N25 . C32 . 108.79(11) yes C30 . N25 . C32 . 108.14(11) yes N25 . C26 . C27 . 115.65(13) yes N25 . C26 . H261 . 105.5 no C27 . C26 . H261 . 110.5 no N25 . C26 . H262 . 104.9 no C27 . C26 . H262 . 110.0 no H261 . C26 . H262 . 110.1 no C26 . C27 . H271 . 108.1 no C26 . C27 . H272 . 112.6 no H271 . C27 . H272 . 109.5 no C26 . C27 . H273 . 110.6 no H271 . C27 . H273 . 108.4 no H272 . C27 . H273 . 107.6 no N25 . C28 . C29 . 115.52(13) yes N25 . C28 . H281 . 103.6 no C29 . C28 . H281 . 110.7 no N25 . C28 . H282 . 105.5 no C29 . C28 . H282 . 109.2 no H281 . C28 . H282 . 112.2 no C28 . C29 . H291 . 109.4 no C28 . C29 . H292 . 107.8 no H291 . C29 . H292 . 112.0 no C28 . C29 . H293 . 108.8 no H291 . C29 . H293 . 109.8 no H292 . C29 . H293 . 108.9 no N25 . C30 . C31 . 115.27(13) yes N25 . C30 . H301 . 105.9 no C31 . C30 . H301 . 109.1 no N25 . C30 . H302 . 106.2 no C31 . C30 . H302 . 109.7 no H301 . C30 . H302 . 110.7 no C30 . C31 . H311 . 106.5 no C30 . C31 . H313 . 109.2 no H311 . C31 . H313 . 107.8 no C30 . C31 . H312 . 111.4 no H311 . C31 . H312 . 111.6 no H313 . C31 . H312 . 110.3 no N25 . C32 . C33 . 115.40(12) yes N25 . C32 . H321 . 103.4 no C33 . C32 . H321 . 110.3 no N25 . C32 . H322 . 106.4 no C33 . C32 . H322 . 112.1 no H321 . C32 . H322 . 108.6 no C32 . C33 . C34 . 121.92(14) yes C32 . C33 . C38 . 119.13(14) yes C34 . C33 . C38 . 118.84(14) yes C33 . C34 . C35 . 120.21(15) yes C33 . C34 . H341 . 119.8 no C35 . C34 . H341 . 119.9 no C34 . C35 . C36 . 120.43(16) yes C34 . C35 . H351 . 120.5 no C36 . C35 . H351 . 119.1 no C35 . C36 . C37 . 119.60(15) yes C35 . C36 . H361 . 119.8 no C37 . C36 . H361 . 120.6 no C36 . C37 . C38 . 120.23(16) yes C36 . C37 . H371 . 120.7 no C38 . C37 . H371 . 119.0 no C33 . C38 . C37 . 120.67(15) yes C33 . C38 . H381 . 119.2 no C37 . C38 . H381 . 120.1 no 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 O3 . C4 . 1.3620(18) yes O3 . H31 . 0.811 no C4 . C5 . 1.416(2) yes C4 . C13 . 1.380(2) yes C5 . C6 . 1.367(2) yes C5 . H51 . 0.969 no C6 . C7 . 1.418(2) yes C6 . H61 . 0.968 no C7 . C8 . 1.424(2) yes C7 . C12 . 1.426(2) yes C8 . C9 . 1.366(3) yes C8 . H81 . 0.981 no C9 . C10 . 1.407(3) yes C9 . H91 . 0.974 no C10 . C11 . 1.372(2) yes C10 . H101 . 0.963 no C11 . C12 . 1.420(2) yes C11 . H111 . 0.968 no C12 . C13 . 1.429(2) yes C13 . C14 . 1.497(2) yes C14 . C15 . 1.377(2) yes C14 . C20 . 1.428(2) yes C15 . O16 . 1.3634(18) yes C15 . C17 . 1.417(2) yes O16 . H161 . 0.873 no C17 . C18 . 1.363(2) yes C17 . H171 . 0.964 no C18 . C19 . 1.417(2) yes C18 . H181 . 0.960 no C19 . C20 . 1.427(2) yes C19 . C24 . 1.422(2) yes C20 . C21 . 1.418(2) yes C21 . C22 . 1.370(2) yes C21 . H211 . 0.958 no C22 . C23 . 1.409(3) yes C22 . H221 . 0.966 no C23 . C24 . 1.365(3) yes C23 . H231 . 0.973 no C24 . H241 . 0.955 no N25 . C26 . 1.5221(19) yes N25 . C28 . 1.5238(19) yes N25 . C30 . 1.5172(19) yes N25 . C32 . 1.5342(19) yes C26 . C27 . 1.513(2) yes C26 . H261 . 1.001 no C26 . H262 . 0.995 no C27 . H271 . 0.964 no C27 . H272 . 0.966 no C27 . H273 . 0.974 no C28 . C29 . 1.510(2) yes C28 . H281 . 0.987 no C28 . H282 . 0.982 no C29 . H291 . 0.986 no C29 . H292 . 0.999 no C29 . H293 . 0.969 no C30 . C31 . 1.515(2) yes C30 . H301 . 0.997 no C30 . H302 . 0.987 no C31 . H311 . 0.986 no C31 . H313 . 0.978 no C31 . H312 . 0.997 no C32 . C33 . 1.508(2) yes C32 . H321 . 0.999 no C32 . H322 . 1.001 no C33 . C34 . 1.390(2) yes C33 . C38 . 1.395(2) yes C34 . C35 . 1.392(2) yes C34 . H341 . 0.971 no C35 . C36 . 1.385(2) yes C35 . H351 . 0.974 no C36 . C37 . 1.381(2) yes C36 . H361 . 0.971 no C37 . C38 . 1.386(2) yes C37 . H371 . 0.968 no C38 . H381 . 0.961 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C28 . H282 . O16 2_556 164.51(5) 0.982 2.259 3.216(2) yes C34 . H341 . O3 . 146.53(5) 0.971 2.438 3.291(2) yes