# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 886458' #TrackingRef 'REVISED_CIF_DATA_OCT_2012.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; propylammonium deoxycholate acetone clathrate ; _chemical_formula_moiety ? _chemical_formula_sum 'C30 H55 N O5' _chemical_formula_weight 509.75 _chemical_absolute_configuration rm loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.0361(11) _cell_length_b 7.7101(7) _cell_length_c 17.9654(18) _cell_angle_alpha 90.00 _cell_angle_beta 105.750(2) _cell_angle_gamma 90.00 _cell_volume 1471.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 13768 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 28.31 _exptl_crystal_description rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.151 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_special_details ; none ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Duo Apex II diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_reflns_number 13768 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 28.31 _reflns_number_total 3922 _reflns_number_gt 3229 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0568P)^2^+0.0966P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3922 _refine_ls_number_parameters 353 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0554 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1023 _refine_ls_wR_factor_gt 0.0950 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7167(2) 0.1166(3) 0.70238(12) 0.0259(4) Uani 1 1 d . . . H14A H 0.6731 0.1244 0.7437 0.031 Uiso 1 1 calc R . . H14B H 0.6786 0.0193 0.6680 0.031 Uiso 1 1 calc R . . C2 C 0.8551(2) 0.0766(3) 0.73907(12) 0.0250(4) Uani 1 1 d . . . H12A H 0.8988 0.0619 0.6981 0.030 Uiso 1 1 calc R . . H12B H 0.8629 -0.0331 0.7686 0.030 Uiso 1 1 calc R . . O3 O 1.04916(14) 0.1975(2) 0.82366(9) 0.0313(4) Uani 1 1 d . . . H6 H 1.0623 0.1012 0.8463 0.038 Uiso 1 1 calc R . . C3 C 0.91647(19) 0.2233(3) 0.79297(11) 0.0242(4) Uani 1 1 d . . . H17 H 0.8769 0.2298 0.8368 0.029 Uiso 1 1 calc R . . C4 C 0.8985(2) 0.3956(3) 0.75086(12) 0.0253(4) Uani 1 1 d . . . H9A H 0.9484 0.3955 0.7127 0.030 Uiso 1 1 calc R . . H9B H 0.9316 0.4892 0.7886 0.030 Uiso 1 1 calc R . . C5 C 0.7604(2) 0.4356(3) 0.70879(12) 0.0242(4) Uani 1 1 d . . . H3 H 0.7147 0.4506 0.7494 0.029 Uiso 1 1 calc R . . C6 C 0.7517(2) 0.6095(3) 0.66535(12) 0.0273(4) Uani 1 1 d . . . H16A H 0.6627 0.6475 0.6491 0.033 Uiso 1 1 calc R . . H16B H 0.8004 0.6984 0.7009 0.033 Uiso 1 1 calc R . . C7 C 0.8017(2) 0.5969(3) 0.59424(12) 0.0261(4) Uani 1 1 d . . . H13A H 0.8936 0.5759 0.6111 0.031 Uiso 1 1 calc R . . H13B H 0.7873 0.7086 0.5660 0.031 Uiso 1 1 calc R . . C8 C 0.73794(19) 0.4506(3) 0.53938(11) 0.0208(4) Uani 1 1 d . . . H8 H 0.6469 0.4797 0.5177 0.025 Uiso 1 1 calc R . . C9 C 0.74833(19) 0.2766(3) 0.58376(11) 0.0207(4) Uani 1 1 d . . . H11 H 0.8403 0.2517 0.6044 0.025 Uiso 1 1 calc R . . C10 C 0.69411(19) 0.2870(3) 0.65506(11) 0.0226(4) Uani 1 1 d . . . C11 C 0.6927(2) 0.1268(3) 0.52809(11) 0.0249(4) Uani 1 1 d . . . H6A H 0.7068 0.0164 0.5573 0.030 Uiso 1 1 calc R . . H6B H 0.6007 0.1440 0.5082 0.030 Uiso 1 1 calc R . . O12 O 0.87854(15) 0.0624(2) 0.48885(9) 0.0338(4) Uani 1 1 d . . . H12 H 0.9075 0.0341 0.4519 0.041 Uiso 1 1 calc R . . C12 C 0.74908(19) 0.1116(3) 0.45950(12) 0.0236(4) Uani 1 1 d . . . H1 H 0.7034 0.0189 0.4239 0.028 Uiso 1 1 calc R . . C13 C 0.73719(18) 0.2850(3) 0.41444(11) 0.0206(4) Uani 1 1 d . . . C14 C 0.79736(18) 0.4291(2) 0.47277(11) 0.0203(4) Uani 1 1 d . . . H4 H 0.8865 0.3929 0.4965 0.024 Uiso 1 1 calc R . . C15 C 0.8030(2) 0.5862(3) 0.42173(12) 0.0259(4) Uani 1 1 d . . . H19A H 0.8735 0.6640 0.4471 0.031 Uiso 1 1 calc R . . H19B H 0.7233 0.6527 0.4101 0.031 Uiso 1 1 calc R . . C16 C 0.8240(2) 0.5060(3) 0.34735(13) 0.0289(5) Uani 1 1 d . . . H24A H 0.9080 0.5385 0.3420 0.035 Uiso 1 1 calc R . . H24B H 0.7593 0.5485 0.3013 0.035 Uiso 1 1 calc R . . C17 C 0.81431(19) 0.3055(3) 0.35440(11) 0.0234(4) Uani 1 1 d . . . H23 H 0.9011 0.2616 0.3793 0.028 Uiso 1 1 calc R . . C18 C 0.59643(19) 0.3191(3) 0.37489(12) 0.0254(4) Uani 1 1 d . . . H10A H 0.5511 0.3336 0.4144 0.038 Uiso 1 1 calc R . . H10B H 0.5610 0.2205 0.3416 0.038 Uiso 1 1 calc R . . H10C H 0.5879 0.4247 0.3435 0.038 Uiso 1 1 calc R . . C19 C 0.5507(2) 0.3175(3) 0.63039(13) 0.0317(5) Uani 1 1 d . . . H22A H 0.5206 0.3337 0.6765 0.048 Uiso 1 1 calc R . . H22B H 0.5086 0.2168 0.6012 0.048 Uiso 1 1 calc R . . H22C H 0.5316 0.4212 0.5978 0.048 Uiso 1 1 calc R . . C20 C 0.7683(2) 0.2143(3) 0.27496(12) 0.0283(5) Uani 1 1 d . . . H26 H 0.6819 0.2580 0.2490 0.034 Uiso 1 1 calc R . . C21 C 0.7609(3) 0.0160(3) 0.28301(16) 0.0463(7) Uani 1 1 d . . . H29A H 0.7416 -0.0375 0.2317 0.069 Uiso 1 1 calc R . . H29B H 0.6945 -0.0128 0.3077 0.069 Uiso 1 1 calc R . . H29C H 0.8418 -0.0278 0.3148 0.069 Uiso 1 1 calc R . . C22 C 0.8551(2) 0.2633(3) 0.22421(11) 0.0284(5) Uani 1 1 d . . . H25A H 0.8556 0.3911 0.2191 0.034 Uiso 1 1 calc R . . H25B H 0.9420 0.2265 0.2510 0.034 Uiso 1 1 calc R . . C23 C 0.8183(2) 0.1834(3) 0.14308(12) 0.0332(5) Uani 1 1 d . . . H28A H 0.8340 0.0569 0.1476 0.040 Uiso 1 1 calc R . . H28B H 0.7270 0.2009 0.1199 0.040 Uiso 1 1 calc R . . C24 C 0.8900(2) 0.2596(3) 0.08883(12) 0.0310(5) Uani 1 1 d . . . O24A O 0.91482(18) 0.4159(2) 0.09080(10) 0.0443(5) Uani 1 1 d . . . O24B O 0.91847(19) 0.1584(2) 0.04109(11) 0.0482(5) Uani 1 1 d . . . O1G O 0.4636(2) 0.5570(4) 0.00634(15) 0.0820(8) Uani 1 1 d . . . N1G N 1.0995(5) 0.3079(7) -0.0179(3) 0.0241(10) Uani 0.809(7) 1 d P A 1 H1G1 H 1.0397 0.2698 0.0046 0.036 Uiso 0.809(7) 1 calc PR A 1 H1G2 H 1.0844 0.2625 -0.0663 0.036 Uiso 0.809(7) 1 calc PR A 1 H1G3 H 1.0969 0.4257 -0.0209 0.036 Uiso 0.809(7) 1 calc PR A 1 C1G C 1.2260(3) 0.2518(4) 0.02936(16) 0.0329(8) Uani 0.809(7) 1 d P A 1 H31A H 1.2916 0.3027 0.0078 0.040 Uiso 0.809(7) 1 calc PR A 1 H31B H 1.2325 0.1240 0.0272 0.040 Uiso 0.809(7) 1 calc PR A 1 C2G C 1.2478(3) 0.3088(5) 0.11257(16) 0.0388(9) Uani 0.809(7) 1 d P A 1 H33A H 1.2397 0.4365 0.1144 0.047 Uiso 0.809(7) 1 calc PR A 1 H33B H 1.1826 0.2568 0.1341 0.047 Uiso 0.809(7) 1 calc PR A 1 C3G C 1.3764(7) 0.2558(10) 0.1617(3) 0.0473(13) Uani 0.809(7) 1 d P A 1 H30A H 1.3835 0.1291 0.1618 0.071 Uiso 0.809(7) 1 calc PR A 1 H30B H 1.3879 0.2972 0.2147 0.071 Uiso 0.809(7) 1 calc PR A 1 H30C H 1.4412 0.3066 0.1404 0.071 Uiso 0.809(7) 1 calc PR A 1 C4G C 0.4000(3) 0.7639(5) 0.0835(2) 0.0663(9) Uani 1 1 d . . . H36A H 0.4222 0.8837 0.0746 0.099 Uiso 1 1 calc R . . H36B H 0.4017 0.7494 0.1380 0.099 Uiso 1 1 calc R . . H36C H 0.3154 0.7379 0.0507 0.099 Uiso 1 1 calc R . . C5G C 0.4922(3) 0.6434(4) 0.06422(16) 0.0475(6) Uani 1 1 d . . . C6G C 0.6199(3) 0.6365(7) 0.1188(2) 0.0831(12) Uani 1 1 d . . . H35A H 0.6727 0.5566 0.0989 0.125 Uiso 1 1 calc R . . H35B H 0.6139 0.5958 0.1694 0.125 Uiso 1 1 calc R . . H35C H 0.6574 0.7526 0.1242 0.125 Uiso 1 1 calc R . . C1F C 1.2088(13) 0.337(2) 0.0527(8) 0.038(4) Uiso 0.191(7) 1 d P A 2 H1F1 H 1.2780 0.3904 0.0353 0.046 Uiso 0.191(7) 1 calc PR A 2 H1F2 H 1.1831 0.4220 0.0869 0.046 Uiso 0.191(7) 1 calc PR A 2 C2F C 1.2579(16) 0.187(3) 0.0980(10) 0.058(5) Uiso 0.191(7) 1 d P A 2 H2F1 H 1.2697 0.0897 0.0649 0.070 Uiso 0.191(7) 1 calc PR A 2 H2F2 H 1.2020 0.1500 0.1298 0.070 Uiso 0.191(7) 1 calc PR A 2 N1F N 1.098(4) 0.310(6) -0.018(2) 0.080(12) Uiso 0.191(7) 1 d P A 2 H1F3 H 1.1266 0.2703 -0.0578 0.120 Uiso 0.191(7) 1 calc PR A 2 H1F4 H 1.0572 0.4124 -0.0314 0.120 Uiso 0.191(7) 1 calc PR A 2 H1F5 H 1.0444 0.2310 -0.0067 0.120 Uiso 0.191(7) 1 calc PR A 2 C3F C 1.402(4) 0.263(8) 0.156(3) 0.096(16) Uiso 0.191(7) 1 d P A 2 H3F1 H 1.4677 0.2447 0.1291 0.144 Uiso 0.191(7) 1 calc PR A 2 H3F2 H 1.4245 0.1997 0.2050 0.144 Uiso 0.191(7) 1 calc PR A 2 H3F3 H 1.3957 0.3871 0.1660 0.144 Uiso 0.191(7) 1 calc PR A 2 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 C1 0.0294(11) 0.0234(10) 0.0268(10) -0.0013(9) 0.0109(8) -0.0047(9) C2 0.0312(11) 0.0193(9) 0.0247(10) 0.0010(8) 0.0080(8) -0.0004(9) O3 0.0312(9) 0.0288(8) 0.0308(8) 0.0006(7) 0.0033(6) 0.0024(7) C3 0.0242(11) 0.0251(10) 0.0235(9) -0.0006(8) 0.0065(8) 0.0004(8) C4 0.0288(11) 0.0213(10) 0.0251(10) -0.0036(8) 0.0060(8) -0.0024(9) C5 0.0288(11) 0.0189(9) 0.0269(10) -0.0029(8) 0.0108(9) 0.0008(8) C6 0.0307(11) 0.0180(9) 0.0332(11) -0.0032(8) 0.0084(9) 0.0032(9) C7 0.0326(11) 0.0146(9) 0.0304(10) -0.0012(8) 0.0077(9) -0.0001(8) C8 0.0189(10) 0.0162(9) 0.0267(10) 0.0002(7) 0.0051(8) 0.0015(7) C9 0.0197(10) 0.0166(9) 0.0252(9) 0.0006(7) 0.0053(7) 0.0004(7) C10 0.0210(10) 0.0213(9) 0.0264(9) -0.0013(8) 0.0082(8) 0.0004(8) C11 0.0275(11) 0.0188(10) 0.0277(10) -0.0016(8) 0.0062(8) -0.0046(8) O12 0.0312(9) 0.0286(8) 0.0409(9) -0.0011(7) 0.0085(7) 0.0113(7) C12 0.0245(11) 0.0177(9) 0.0284(10) -0.0018(8) 0.0067(8) -0.0022(8) C13 0.0172(9) 0.0182(9) 0.0259(9) -0.0020(8) 0.0051(7) -0.0001(8) C14 0.0164(10) 0.0168(9) 0.0274(10) -0.0002(8) 0.0055(8) -0.0005(8) C15 0.0291(11) 0.0188(10) 0.0304(10) 0.0020(8) 0.0091(8) -0.0013(9) C16 0.0363(13) 0.0226(10) 0.0301(11) -0.0003(9) 0.0129(9) -0.0050(9) C17 0.0219(10) 0.0210(9) 0.0282(10) -0.0025(8) 0.0083(8) -0.0030(8) C18 0.0189(10) 0.0274(11) 0.0282(10) -0.0013(8) 0.0034(8) -0.0011(8) C19 0.0230(11) 0.0352(12) 0.0389(12) -0.0018(10) 0.0117(9) 0.0012(9) C20 0.0287(12) 0.0308(11) 0.0276(10) -0.0053(9) 0.0115(9) -0.0072(9) C21 0.0707(19) 0.0331(13) 0.0455(14) -0.0139(11) 0.0336(14) -0.0212(13) C22 0.0301(11) 0.0286(11) 0.0284(10) -0.0034(9) 0.0111(9) -0.0049(9) C23 0.0336(12) 0.0361(12) 0.0329(11) -0.0098(10) 0.0142(9) -0.0109(10) C24 0.0323(12) 0.0350(12) 0.0270(10) -0.0067(9) 0.0099(9) -0.0078(10) O24A 0.0656(13) 0.0346(9) 0.0396(9) -0.0100(8) 0.0261(9) -0.0156(9) O24B 0.0669(13) 0.0374(10) 0.0541(11) -0.0157(9) 0.0402(10) -0.0135(9) O1G 0.0748(18) 0.094(2) 0.0715(14) -0.0314(16) 0.0107(13) -0.0001(15) N1G 0.0278(16) 0.0244(13) 0.0194(13) -0.0040(8) 0.0054(9) -0.0004(9) C1G 0.0360(16) 0.0328(16) 0.0289(15) -0.0035(13) 0.0070(12) 0.0039(13) C2G 0.0440(19) 0.0443(19) 0.0265(15) -0.0027(13) 0.0069(13) 0.0024(15) C3G 0.041(3) 0.063(3) 0.0314(19) 0.0078(17) -0.0015(18) -0.008(2) C4G 0.072(2) 0.065(2) 0.069(2) 0.0077(18) 0.0318(18) 0.0081(18) C5G 0.0479(16) 0.0491(16) 0.0437(14) 0.0042(13) 0.0096(12) -0.0045(13) C6G 0.051(2) 0.117(4) 0.070(2) -0.004(2) -0.0026(16) 0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.523(3) . ? C1 C10 1.548(3) . ? C1 H14A 0.9900 . ? C1 H14B 0.9900 . ? C2 C3 1.523(3) . ? C2 H12A 0.9900 . ? C2 H12B 0.9900 . ? O3 C3 1.432(3) . ? O3 H6 0.8400 . ? C3 C4 1.515(3) . ? C3 H17 1.0000 . ? C4 C5 1.537(3) . ? C4 H9A 0.9900 . ? C4 H9B 0.9900 . ? C5 C6 1.541(3) . ? C5 C10 1.548(3) . ? C5 H3 1.0000 . ? C6 C7 1.526(3) . ? C6 H16A 0.9900 . ? C6 H16B 0.9900 . ? C7 C8 1.537(3) . ? C7 H13A 0.9900 . ? C7 H13B 0.9900 . ? C8 C14 1.522(3) . ? C8 C9 1.549(3) . ? C8 H8 1.0000 . ? C9 C11 1.542(3) . ? C9 C10 1.556(3) . ? C9 H11 1.0000 . ? C10 C19 1.542(3) . ? C11 C12 1.528(3) . ? C11 H6A 0.9900 . ? C11 H6B 0.9900 . ? O12 C12 1.433(2) . ? O12 H12 0.8400 . ? C12 C13 1.550(3) . ? C12 H1 1.0000 . ? C13 C18 1.545(3) . ? C13 C14 1.547(3) . ? C13 C17 1.553(3) . ? C14 C15 1.531(3) . ? C14 H4 1.0000 . ? C15 C16 1.546(3) . ? C15 H19A 0.9900 . ? C15 H19B 0.9900 . ? C16 C17 1.557(3) . ? C16 H24A 0.9900 . ? C16 H24B 0.9900 . ? C17 C20 1.548(3) . ? C17 H23 1.0000 . ? C18 H10A 0.9800 . ? C18 H10B 0.9800 . ? C18 H10C 0.9800 . ? C19 H22A 0.9800 . ? C19 H22B 0.9800 . ? C19 H22C 0.9800 . ? C20 C22 1.538(3) . ? C20 C21 1.540(3) . ? C20 H26 1.0000 . ? C21 H29A 0.9800 . ? C21 H29B 0.9800 . ? C21 H29C 0.9800 . ? C22 C23 1.532(3) . ? C22 H25A 0.9900 . ? C22 H25B 0.9900 . ? C23 C24 1.529(3) . ? C23 H28A 0.9900 . ? C23 H28B 0.9900 . ? C24 O24A 1.234(3) . ? C24 O24B 1.261(3) . ? O1G C5G 1.203(4) . ? N1G C1G 1.488(6) . ? N1G H1G1 0.9100 . ? N1G H1G2 0.9100 . ? N1G H1G3 0.9100 . ? C1G C2G 1.513(4) . ? C1G H31A 0.9900 . ? C1G H31B 0.9900 . ? C2G C3G 1.510(7) . ? C2G H33A 0.9900 . ? C2G H33B 0.9900 . ? C3G H30A 0.9800 . ? C3G H30B 0.9800 . ? C3G H30C 0.9800 . ? C4G C5G 1.486(5) . ? C4G H36A 0.9800 . ? C4G H36B 0.9800 . ? C4G H36C 0.9800 . ? C5G C6G 1.484(4) . ? C6G H35A 0.9800 . ? C6G H35B 0.9800 . ? C6G H35C 0.9800 . ? C1F C2F 1.43(2) . ? C1F N1F 1.52(4) . ? C1F H1F1 0.9900 . ? C1F H1F2 0.9900 . ? C2F C3F 1.75(5) . ? C2F H2F1 0.9900 . ? C2F H2F2 0.9900 . ? N1F H1F3 0.9100 . ? N1F H1F4 0.9100 . ? N1F H1F5 0.9100 . ? C3F H3F1 0.9800 . ? C3F H3F2 0.9800 . ? C3F H3F3 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C10 113.74(16) . . ? C2 C1 H14A 108.8 . . ? C10 C1 H14A 108.8 . . ? C2 C1 H14B 108.8 . . ? C10 C1 H14B 108.8 . . ? H14A C1 H14B 107.7 . . ? C1 C2 C3 110.21(17) . . ? C1 C2 H12A 109.6 . . ? C3 C2 H12A 109.6 . . ? C1 C2 H12B 109.6 . . ? C3 C2 H12B 109.6 . . ? H12A C2 H12B 108.1 . . ? C3 O3 H6 109.5 . . ? O3 C3 C4 107.23(16) . . ? O3 C3 C2 111.90(17) . . ? C4 C3 C2 111.00(16) . . ? O3 C3 H17 108.9 . . ? C4 C3 H17 108.9 . . ? C2 C3 H17 108.9 . . ? C3 C4 C5 113.54(17) . . ? C3 C4 H9A 108.9 . . ? C5 C4 H9A 108.9 . . ? C3 C4 H9B 108.9 . . ? C5 C4 H9B 108.9 . . ? H9A C4 H9B 107.7 . . ? C4 C5 C6 109.93(17) . . ? C4 C5 C10 113.32(16) . . ? C6 C5 C10 111.97(16) . . ? C4 C5 H3 107.1 . . ? C6 C5 H3 107.1 . . ? C10 C5 H3 107.1 . . ? C7 C6 C5 112.41(16) . . ? C7 C6 H16A 109.1 . . ? C5 C6 H16A 109.1 . . ? C7 C6 H16B 109.1 . . ? C5 C6 H16B 109.1 . . ? H16A C6 H16B 107.9 . . ? C6 C7 C8 112.14(17) . . ? C6 C7 H13A 109.2 . . ? C8 C7 H13A 109.2 . . ? C6 C7 H13B 109.2 . . ? C8 C7 H13B 109.2 . . ? H13A C7 H13B 107.9 . . ? C14 C8 C7 111.36(17) . . ? C14 C8 C9 108.84(15) . . ? C7 C8 C9 110.40(15) . . ? C14 C8 H8 108.7 . . ? C7 C8 H8 108.7 . . ? C9 C8 H8 108.7 . . ? C11 C9 C8 110.73(15) . . ? C11 C9 C10 113.48(16) . . ? C8 C9 C10 112.80(15) . . ? C11 C9 H11 106.4 . . ? C8 C9 H11 106.4 . . ? C10 C9 H11 106.4 . . ? C19 C10 C1 106.66(17) . . ? C19 C10 C5 109.95(17) . . ? C1 C10 C5 107.90(15) . . ? C19 C10 C9 111.43(16) . . ? C1 C10 C9 111.58(16) . . ? C5 C10 C9 109.23(16) . . ? C12 C11 C9 113.75(17) . . ? C12 C11 H6A 108.8 . . ? C9 C11 H6A 108.8 . . ? C12 C11 H6B 108.8 . . ? C9 C11 H6B 108.8 . . ? H6A C11 H6B 107.7 . . ? C12 O12 H12 109.5 . . ? O12 C12 C11 107.87(16) . . ? O12 C12 C13 110.82(16) . . ? C11 C12 C13 111.10(16) . . ? O12 C12 H1 109.0 . . ? C11 C12 H1 109.0 . . ? C13 C12 H1 109.0 . . ? C18 C13 C14 112.49(16) . . ? C18 C13 C12 108.59(16) . . ? C14 C13 C12 107.78(15) . . ? C18 C13 C17 109.60(16) . . ? C14 C13 C17 100.48(15) . . ? C12 C13 C17 117.77(16) . . ? C8 C14 C15 118.75(16) . . ? C8 C14 C13 114.42(16) . . ? C15 C14 C13 104.02(15) . . ? C8 C14 H4 106.3 . . ? C15 C14 H4 106.3 . . ? C13 C14 H4 106.3 . . ? C14 C15 C16 103.96(16) . . ? C14 C15 H19A 111.0 . . ? C16 C15 H19A 111.0 . . ? C14 C15 H19B 111.0 . . ? C16 C15 H19B 111.0 . . ? H19A C15 H19B 109.0 . . ? C15 C16 C17 107.28(17) . . ? C15 C16 H24A 110.3 . . ? C17 C16 H24A 110.3 . . ? C15 C16 H24B 110.3 . . ? C17 C16 H24B 110.3 . . ? H24A C16 H24B 108.5 . . ? C20 C17 C13 119.34(16) . . ? C20 C17 C16 112.86(17) . . ? C13 C17 C16 102.73(16) . . ? C20 C17 H23 107.1 . . ? C13 C17 H23 107.1 . . ? C16 C17 H23 107.1 . . ? C13 C18 H10A 109.5 . . ? C13 C18 H10B 109.5 . . ? H10A C18 H10B 109.5 . . ? C13 C18 H10C 109.5 . . ? H10A C18 H10C 109.5 . . ? H10B C18 H10C 109.5 . . ? C10 C19 H22A 109.5 . . ? C10 C19 H22B 109.5 . . ? H22A C19 H22B 109.5 . . ? C10 C19 H22C 109.5 . . ? H22A C19 H22C 109.5 . . ? H22B C19 H22C 109.5 . . ? C22 C20 C21 110.9(2) . . ? C22 C20 C17 109.52(17) . . ? C21 C20 C17 112.1(2) . . ? C22 C20 H26 108.0 . . ? C21 C20 H26 108.0 . . ? C17 C20 H26 108.0 . . ? C20 C21 H29A 109.5 . . ? C20 C21 H29B 109.5 . . ? H29A C21 H29B 109.5 . . ? C20 C21 H29C 109.5 . . ? H29A C21 H29C 109.5 . . ? H29B C21 H29C 109.5 . . ? C23 C22 C20 114.75(18) . . ? C23 C22 H25A 108.6 . . ? C20 C22 H25A 108.6 . . ? C23 C22 H25B 108.6 . . ? C20 C22 H25B 108.6 . . ? H25A C22 H25B 107.6 . . ? C24 C23 C22 113.74(18) . . ? C24 C23 H28A 108.8 . . ? C22 C23 H28A 108.8 . . ? C24 C23 H28B 108.8 . . ? C22 C23 H28B 108.8 . . ? H28A C23 H28B 107.7 . . ? O24A C24 O24B 122.0(2) . . ? O24A C24 C23 120.4(2) . . ? O24B C24 C23 117.6(2) . . ? N1G C1G C2G 110.6(3) . . ? N1G C1G H31A 109.5 . . ? C2G C1G H31A 109.5 . . ? N1G C1G H31B 109.5 . . ? C2G C1G H31B 109.5 . . ? H31A C1G H31B 108.1 . . ? C3G C2G C1G 111.8(4) . . ? C3G C2G H33A 109.3 . . ? C1G C2G H33A 109.3 . . ? C3G C2G H33B 109.3 . . ? C1G C2G H33B 109.3 . . ? H33A C2G H33B 107.9 . . ? C5G C4G H36A 109.5 . . ? C5G C4G H36B 109.5 . . ? H36A C4G H36B 109.5 . . ? C5G C4G H36C 109.5 . . ? H36A C4G H36C 109.5 . . ? H36B C4G H36C 109.5 . . ? O1G C5G C6G 122.1(3) . . ? O1G C5G C4G 120.8(3) . . ? C6G C5G C4G 117.1(3) . . ? C5G C6G H35A 109.5 . . ? C5G C6G H35B 109.5 . . ? H35A C6G H35B 109.5 . . ? C5G C6G H35C 109.5 . . ? H35A C6G H35C 109.5 . . ? H35B C6G H35C 109.5 . . ? C2F C1F N1F 117(2) . . ? C2F C1F H1F1 108.0 . . ? N1F C1F H1F1 108.0 . . ? C2F C1F H1F2 108.0 . . ? N1F C1F H1F2 108.0 . . ? H1F1 C1F H1F2 107.2 . . ? C1F C2F C3F 102(2) . . ? C1F C2F H2F1 111.3 . . ? C3F C2F H2F1 111.3 . . ? C1F C2F H2F2 111.3 . . ? C3F C2F H2F2 111.3 . . ? H2F1 C2F H2F2 109.2 . . ? C1F N1F H1F3 109.5 . . ? C1F N1F H1F4 109.5 . . ? H1F3 N1F H1F4 109.5 . . ? C1F N1F H1F5 109.5 . . ? H1F3 N1F H1F5 109.5 . . ? H1F4 N1F H1F5 109.5 . . ? C2F C3F H3F1 109.5 . . ? C2F C3F H3F2 109.5 . . ? H3F1 C3F H3F2 109.5 . . ? C2F C3F H3F3 109.5 . . ? H3F1 C3F H3F3 109.5 . . ? H3F2 C3F H3F3 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C1 C2 C3 59.0(2) . . . . ? C1 C2 C3 O3 -175.14(16) . . . . ? C1 C2 C3 C4 -55.4(2) . . . . ? O3 C3 C4 C5 175.34(16) . . . . ? C2 C3 C4 C5 52.8(2) . . . . ? C3 C4 C5 C6 -177.99(16) . . . . ? C3 C4 C5 C10 -51.8(2) . . . . ? C4 C5 C6 C7 72.1(2) . . . . ? C10 C5 C6 C7 -54.8(2) . . . . ? C5 C6 C7 C8 54.1(2) . . . . ? C6 C7 C8 C14 -174.72(16) . . . . ? C6 C7 C8 C9 -53.7(2) . . . . ? C14 C8 C9 C11 -53.6(2) . . . . ? C7 C8 C9 C11 -176.11(17) . . . . ? C14 C8 C9 C10 178.00(16) . . . . ? C7 C8 C9 C10 55.5(2) . . . . ? C2 C1 C10 C19 -173.65(17) . . . . ? C2 C1 C10 C5 -55.5(2) . . . . ? C2 C1 C10 C9 64.4(2) . . . . ? C4 C5 C10 C19 166.78(17) . . . . ? C6 C5 C10 C19 -68.2(2) . . . . ? C4 C5 C10 C1 50.8(2) . . . . ? C6 C5 C10 C1 175.86(17) . . . . ? C4 C5 C10 C9 -70.6(2) . . . . ? C6 C5 C10 C9 54.4(2) . . . . ? C11 C9 C10 C19 -60.9(2) . . . . ? C8 C9 C10 C19 66.1(2) . . . . ? C11 C9 C10 C1 58.2(2) . . . . ? C8 C9 C10 C1 -174.84(16) . . . . ? C11 C9 C10 C5 177.40(16) . . . . ? C8 C9 C10 C5 -55.6(2) . . . . ? C8 C9 C11 C12 54.1(2) . . . . ? C10 C9 C11 C12 -177.86(16) . . . . ? C9 C11 C12 O12 66.6(2) . . . . ? C9 C11 C12 C13 -55.0(2) . . . . ? O12 C12 C13 C18 172.39(16) . . . . ? C11 C12 C13 C18 -67.7(2) . . . . ? O12 C12 C13 C14 -65.49(19) . . . . ? C11 C12 C13 C14 54.4(2) . . . . ? O12 C12 C13 C17 47.1(2) . . . . ? C11 C12 C13 C17 167.04(16) . . . . ? C7 C8 C14 C15 -55.9(2) . . . . ? C9 C8 C14 C15 -177.81(17) . . . . ? C7 C8 C14 C13 -179.42(16) . . . . ? C9 C8 C14 C13 58.6(2) . . . . ? C18 C13 C14 C8 60.9(2) . . . . ? C12 C13 C14 C8 -58.8(2) . . . . ? C17 C13 C14 C8 177.38(16) . . . . ? C18 C13 C14 C15 -70.2(2) . . . . ? C12 C13 C14 C15 170.09(15) . . . . ? C17 C13 C14 C15 46.25(18) . . . . ? C8 C14 C15 C16 -161.12(18) . . . . ? C13 C14 C15 C16 -32.6(2) . . . . ? C14 C15 C16 C17 6.4(2) . . . . ? C18 C13 C17 C20 -48.1(2) . . . . ? C14 C13 C17 C20 -166.73(18) . . . . ? C12 C13 C17 C20 76.6(2) . . . . ? C18 C13 C17 C16 77.60(19) . . . . ? C14 C13 C17 C16 -41.01(19) . . . . ? C12 C13 C17 C16 -157.65(18) . . . . ? C15 C16 C17 C20 151.72(18) . . . . ? C15 C16 C17 C13 21.9(2) . . . . ? C13 C17 C20 C22 176.47(18) . . . . ? C16 C17 C20 C22 55.7(2) . . . . ? C13 C17 C20 C21 -60.0(3) . . . . ? C16 C17 C20 C21 179.3(2) . . . . ? C21 C20 C22 C23 56.7(3) . . . . ? C17 C20 C22 C23 -179.03(19) . . . . ? C20 C22 C23 C24 169.2(2) . . . . ? C22 C23 C24 O24A -37.9(3) . . . . ? C22 C23 C24 O24B 144.3(2) . . . . ? N1G C1G C2G C3G -179.2(4) . . . . ? N1F C1F C2F C3F 166(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.274 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.036 _chemical_name_common 'propylammonium deoxycholate acetone clathrate' data_c:\ _database_code_depnum_ccdc_archive 'CCDC 886459' #TrackingRef 'H_PPA_4.3WATER.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; di-(propylammonium deoxycholate) hydrate ; _chemical_formula_moiety ? _chemical_formula_sum 'C54 H106.26 N2 O12.30' _chemical_formula_weight 980.47 _chemical_absolute_configuration rm loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 7.7287(6) _cell_length_b 11.5210(9) _cell_length_c 16.5589(13) _cell_angle_alpha 81.143(2) _cell_angle_beta 79.051(2) _cell_angle_gamma 89.485(2) _cell_volume 1430.03(19) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 11575 _cell_measurement_theta_min 0.17 _cell_measurement_theta_max 28.38 _exptl_crystal_description rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.138 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 542.7 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_special_details ; none ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Duo Apex II diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_reflns_number 11575 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0467 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 28.38 _reflns_number_total 7136 _reflns_number_gt 6048 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0648P)^2^+0.0250P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 7136 _refine_ls_number_parameters 749 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1134 _refine_ls_wR_factor_gt 0.1070 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O12B O 0.7634(2) 0.20488(15) 0.79047(10) 0.0274(4) Uani 1 1 d . . . O24B O 0.8472(3) -0.30162(16) 0.64235(11) 0.0321(4) Uani 1 1 d . . . C9B C 0.5378(3) 0.3049(2) 0.93659(14) 0.0215(4) Uani 1 1 d . . . H7 H 0.5003 0.3242 0.8816 0.026 Uiso 1 1 calc R . . C13B C 0.7153(3) 0.07561(19) 0.92224(14) 0.0203(4) Uani 1 1 d . . . C17B C 0.7415(3) -0.03546(19) 0.87864(14) 0.0219(4) Uani 1 1 d . . . H9 H 0.7278 -0.0112 0.8196 0.026 Uiso 1 1 calc R . . C11B C 0.7381(3) 0.2948(2) 0.91689(15) 0.0245(5) Uani 1 1 d . . . H10A H 0.7829 0.2871 0.9696 0.029 Uiso 1 1 calc R . . H10B H 0.7890 0.3684 0.8817 0.029 Uiso 1 1 calc R . . O13 O 1.0883(3) -0.36082(17) 0.50893(13) 0.0385(5) Uani 1 1 d . . . O24A O 0.9744(3) -0.39425(16) 0.74251(13) 0.0376(5) Uani 1 1 d . . . C7B C 0.2429(3) 0.2012(2) 0.98431(16) 0.0280(5) Uani 1 1 d . . . H16A H 0.1815 0.1278 1.0148 0.034 Uiso 1 1 calc R . . H16B H 0.2175 0.2134 0.9273 0.034 Uiso 1 1 calc R . . C12B C 0.8032(3) 0.1905(2) 0.87203(14) 0.0222(4) Uani 1 1 d . . . H17 H 0.9338 0.1850 0.8676 0.027 Uiso 1 1 calc R . . C4B C 0.2253(4) 0.4669(2) 0.90378(17) 0.0318(5) Uani 1 1 d . . . H19A H 0.2511 0.4057 0.8675 0.038 Uiso 1 1 calc R . . H19B H 0.0973 0.4819 0.9112 0.038 Uiso 1 1 calc R . . O3B O 0.3006(3) 0.61064(18) 0.77703(13) 0.0412(5) Uani 1 1 d D . . C14B C 0.5133(3) 0.08883(19) 0.93242(14) 0.0210(4) Uani 1 1 d . . . H21 H 0.4867 0.1082 0.8751 0.025 Uiso 1 1 calc R . . C10B C 0.4730(3) 0.4073(2) 0.98530(16) 0.0266(5) Uani 1 1 d . . . C24B C 0.9023(3) -0.3069(2) 0.71017(15) 0.0258(5) Uani 1 1 d . . . C5B C 0.2715(3) 0.4203(2) 0.98936(17) 0.0301(5) Uani 1 1 d . . . H27 H 0.2304 0.4793 1.0268 0.036 Uiso 1 1 calc R . . C6B C 0.1714(3) 0.3042(2) 1.02811(17) 0.0311(5) Uani 1 1 d . . . H28A H 0.1802 0.2862 1.0876 0.037 Uiso 1 1 calc R . . H28B H 0.0452 0.3136 1.0251 0.037 Uiso 1 1 calc R . . C8B C 0.4412(3) 0.1878(2) 0.97946(14) 0.0222(4) Uani 1 1 d . . . H29 H 0.4645 0.1698 1.0374 0.027 Uiso 1 1 calc R . . C1B C 0.5634(3) 0.5254(2) 0.94279(18) 0.0309(5) Uani 1 1 d . . . H33A H 0.5249 0.5860 0.9784 0.037 Uiso 1 1 calc R . . H33B H 0.6925 0.5178 0.9380 0.037 Uiso 1 1 calc R . . C23B C 0.8721(4) -0.1990(2) 0.75373(15) 0.0269(5) Uani 1 1 d . . . H40A H 0.9452 -0.1329 0.7189 0.032 Uiso 1 1 calc R . . H40B H 0.7471 -0.1768 0.7574 0.032 Uiso 1 1 calc R . . C16B C 0.5789(3) -0.1152(2) 0.92388(15) 0.0282(5) Uani 1 1 d . . . H41A H 0.5290 -0.1526 0.8832 0.034 Uiso 1 1 calc R . . H41B H 0.6140 -0.1777 0.9654 0.034 Uiso 1 1 calc R . . C2B C 0.5233(4) 0.5662(2) 0.85692(18) 0.0321(6) Uani 1 1 d . . . H42A H 0.5684 0.5085 0.8199 0.039 Uiso 1 1 calc R . . H42B H 0.5843 0.6425 0.8332 0.039 Uiso 1 1 calc R . . C3B C 0.3267(4) 0.5795(2) 0.86063(18) 0.0334(6) Uani 1 1 d . . . H44 H 0.2850 0.6449 0.8924 0.040 Uiso 1 1 calc R . . C18B C 0.7751(3) 0.0514(2) 1.00622(15) 0.0271(5) Uani 1 1 d . . . H45A H 0.7353 -0.0277 1.0343 0.041 Uiso 1 1 calc R . . H45B H 0.7242 0.1094 1.0410 0.041 Uiso 1 1 calc R . . H45C H 0.9040 0.0569 0.9971 0.041 Uiso 1 1 calc R . . C15B C 0.4417(3) -0.0360(2) 0.96726(16) 0.0273(5) Uani 1 1 d . . . H46A H 0.3244 -0.0478 0.9537 0.033 Uiso 1 1 calc R . . H46B H 0.4319 -0.0523 1.0284 0.033 Uiso 1 1 calc R . . C20B C 0.9168(3) -0.0995(2) 0.87707(16) 0.0271(5) Uani 1 1 d . . . H47 H 0.9323 -0.1209 0.9361 0.033 Uiso 1 1 calc R . . C19B C 0.5114(4) 0.3858(3) 1.07464(17) 0.0364(6) Uani 1 1 d . . . H48A H 0.4601 0.4487 1.1047 0.055 Uiso 1 1 calc R . . H48B H 0.6392 0.3852 1.0721 0.055 Uiso 1 1 calc R . . H48C H 0.4594 0.3100 1.1038 0.055 Uiso 1 1 calc R . . C22B C 0.9146(4) -0.2150(2) 0.84069(16) 0.0289(5) Uani 1 1 d . . . H54A H 1.0314 -0.2516 0.8390 0.035 Uiso 1 1 calc R . . H54B H 0.8262 -0.2699 0.8784 0.035 Uiso 1 1 calc R . . C21B C 1.0763(4) -0.0229(2) 0.83024(19) 0.0346(6) Uani 1 1 d . . . H56A H 1.0975 0.0377 0.8630 0.052 Uiso 1 1 calc R . . H56B H 1.0531 0.0145 0.7762 0.052 Uiso 1 1 calc R . . H56C H 1.1804 -0.0720 0.8216 0.052 Uiso 1 1 calc R . . O12A O 1.0082(2) 0.83435(14) 0.40761(10) 0.0262(4) Uani 1 1 d D . . O24D O 1.1386(3) 1.43348(15) 0.45391(12) 0.0337(4) Uani 1 1 d . . . C13A C 1.0661(3) 0.96141(19) 0.27440(13) 0.0206(4) Uani 1 1 d . . . C9A C 0.8956(3) 0.7337(2) 0.26260(15) 0.0224(4) Uani 1 1 d . . . H6 H 0.8120 0.7185 0.3173 0.027 Uiso 1 1 calc R . . C11A C 1.0802(3) 0.7405(2) 0.28277(15) 0.0234(5) Uani 1 1 d . . . H12A H 1.1681 0.7441 0.2304 0.028 Uiso 1 1 calc R . . H12B H 1.1000 0.6675 0.3197 0.028 Uiso 1 1 calc R . . C12A C 1.1127(3) 0.84610(19) 0.32484(14) 0.0217(4) Uani 1 1 d . . . H15 H 1.2401 0.8494 0.3285 0.026 Uiso 1 1 calc R . . O24C O 0.9417(3) 1.32789(18) 0.55194(13) 0.0447(5) Uani 1 1 d . . . C24A C 1.0577(4) 1.3394(2) 0.48697(16) 0.0294(5) Uani 1 1 d . . . C17A C 1.0578(3) 1.07321(19) 0.31640(14) 0.0222(5) Uani 1 1 d . . . H17A H 0.9954 1.0503 0.3754 0.027 Uiso 1 1 calc R . . C14A C 0.8738(3) 0.9510(2) 0.26294(14) 0.0217(4) Uani 1 1 d . . . H26 H 0.7994 0.9330 0.3199 0.026 Uiso 1 1 calc R . . C5A C 0.6731(4) 0.6237(2) 0.20585(17) 0.0316(5) Uani 1 1 d . . . H30 H 0.6640 0.5639 0.1689 0.038 Uiso 1 1 calc R . . C18A C 1.1956(3) 0.9834(2) 0.19048(15) 0.0264(5) Uani 1 1 d . . . H31A H 1.1757 1.0612 0.1607 0.040 Uiso 1 1 calc R . . H31B H 1.1769 0.9232 0.1570 0.040 Uiso 1 1 calc R . . H31C H 1.3168 0.9799 0.2003 0.040 Uiso 1 1 calc R . . C8A C 0.8405(3) 0.8513(2) 0.21634(14) 0.0230(5) Uani 1 1 d . . . H32 H 0.9156 0.8662 0.1594 0.028 Uiso 1 1 calc R . . C4A C 0.5471(3) 0.5839(2) 0.28932(18) 0.0327(6) Uani 1 1 d . . . H34A H 0.5424 0.6467 0.3242 0.039 Uiso 1 1 calc R . . H34B H 0.4271 0.5731 0.2785 0.039 Uiso 1 1 calc R . . C10A C 0.8688(3) 0.6296(2) 0.21604(17) 0.0289(5) Uani 1 1 d . . . C7A C 0.6479(3) 0.8433(2) 0.20746(16) 0.0277(5) Uani 1 1 d . . . H36A H 0.5716 0.8331 0.2634 0.033 Uiso 1 1 calc R . . H36B H 0.6160 0.9177 0.1756 0.033 Uiso 1 1 calc R . . C20A C 1.2305(3) 1.1365(2) 0.31882(15) 0.0270(5) Uani 1 1 d . . . H38 H 1.2928 1.1599 0.2599 0.032 Uiso 1 1 calc R . . C6A C 0.6145(4) 0.7414(3) 0.16331(17) 0.0349(6) Uani 1 1 d . . . H39A H 0.6790 0.7570 0.1049 0.042 Uiso 1 1 calc R . . H39B H 0.4871 0.7362 0.1624 0.042 Uiso 1 1 calc R . . C16A C 0.9321(4) 1.1544(2) 0.27070(16) 0.0294(5) Uani 1 1 d . . . H50A H 0.8487 1.1926 0.3112 0.035 Uiso 1 1 calc R . . H50B H 1.0010 1.2165 0.2294 0.035 Uiso 1 1 calc R . . C23A C 1.0988(4) 1.2298(2) 0.44711(16) 0.0368(6) Uani 1 1 d . . . H51A H 0.9864 1.1874 0.4499 0.044 Uiso 1 1 calc R . . H51B H 1.1703 1.1780 0.4807 0.044 Uiso 1 1 calc R . . C22A C 1.1959(4) 1.2496(2) 0.35722(16) 0.0295(5) Uani 1 1 d . . . H52A H 1.3102 1.2897 0.3542 0.035 Uiso 1 1 calc R . . H52B H 1.1262 1.3026 0.3235 0.035 Uiso 1 1 calc R . . C19A C 0.9900(4) 0.6432(3) 0.12957(19) 0.0406(7) Uani 1 1 d . . . H53A H 0.9614 0.5813 0.0995 0.061 Uiso 1 1 calc R . . H53B H 1.1132 0.6368 0.1362 0.061 Uiso 1 1 calc R . . H53C H 0.9725 0.7202 0.0980 0.061 Uiso 1 1 calc R . . C2A C 0.7897(4) 0.4768(2) 0.3479(2) 0.0357(6) Uani 1 1 d . . . H55A H 0.8233 0.3994 0.3750 0.043 Uiso 1 1 calc R . . H55B H 0.8024 0.5355 0.3843 0.043 Uiso 1 1 calc R . . C1A C 0.9111(4) 0.5105(2) 0.26413(19) 0.0349(6) Uani 1 1 d . . . H58A H 0.9032 0.4485 0.2296 0.042 Uiso 1 1 calc R . . H58B H 1.0341 0.5137 0.2729 0.042 Uiso 1 1 calc R . . C3A C 0.6003(4) 0.4709(2) 0.33722(18) 0.0342(6) Uani 1 1 d . . . H60B H 0.585(4) 0.404(3) 0.306(2) 0.041 Uiso 1 1 d . . . C15A C 0.8311(4) 1.0765(2) 0.22690(16) 0.0288(5) Uani 1 1 d . . . H61A H 0.7028 1.0900 0.2397 0.035 Uiso 1 1 calc R . . H61B H 0.8725 1.0919 0.1658 0.035 Uiso 1 1 calc R . . C21A C 1.3552(4) 1.0578(3) 0.3640(2) 0.0374(6) Uani 1 1 d . . . H62A H 1.2884 1.0153 0.4163 0.056 Uiso 1 1 calc R . . H62B H 1.4476 1.1066 0.3760 0.056 Uiso 1 1 calc R . . H62C H 1.4091 1.0014 0.3286 0.056 Uiso 1 1 calc R . . N1G N 0.8060(3) 0.9122(2) 0.54997(15) 0.0300(5) Uani 1 1 d D . . C1G C 0.6230(4) 0.9163(3) 0.53442(18) 0.0374(6) Uani 1 1 d . . . H59A H 0.6056 0.8555 0.5003 0.045 Uiso 1 1 calc R . . H59B H 0.6028 0.9940 0.5031 0.045 Uiso 1 1 calc R . . C2G C 0.4925(5) 0.8953(4) 0.6160(2) 0.0513(8) Uani 1 1 d . . . H64A H 0.5117 0.9556 0.6503 0.062 Uiso 1 1 calc R . . H64B H 0.5129 0.8174 0.6470 0.062 Uiso 1 1 calc R . . C3G C 0.3030(5) 0.9002(5) 0.6026(3) 0.0760(13) Uani 1 1 d . . . H65A H 0.2879 0.8486 0.5625 0.114 Uiso 1 1 calc R . . H65B H 0.2761 0.9810 0.5811 0.114 Uiso 1 1 calc R . . H65C H 0.2230 0.8741 0.6557 0.114 Uiso 1 1 calc R . . O43 O 0.8481(5) 0.4174(2) 0.69234(16) 0.0426(11) Uani 0.828(9) 1 d P A 3 O49 O 0.8409(4) 0.10535(19) 0.63364(14) 0.0510(6) Uani 1 1 d D . . O57 O 0.4574(4) 0.6464(2) 0.49932(16) 0.0542(6) Uani 1 1 d D . . N1GB N 0.512(5) 0.520(2) 0.648(2) 0.058(9) Uani 0.357(12) 1 d P B 1 C32A C 0.5091(10) 0.3993(6) 0.6543(5) 0.063(2) Uani 0.643(12) 1 d P B 2 H2A1 H 0.5430 0.3597 0.7063 0.076 Uiso 0.643(12) 1 calc PR B 2 H2A2 H 0.5862 0.3705 0.6068 0.076 Uiso 0.643(12) 1 calc PR B 2 C32B C 0.3231(11) 0.3692(6) 0.6548(5) 0.062(2) Uani 0.643(12) 1 d P B 2 H2B1 H 0.2913 0.4057 0.6015 0.075 Uiso 0.643(12) 1 calc PR B 2 H2B2 H 0.2459 0.4017 0.7004 0.075 Uiso 0.643(12) 1 calc PR B 2 C1C C 0.345(3) 0.1961(14) 0.6664(17) 0.075(5) Uani 0.357(12) 1 d P B 1 H1C1 H 0.4152 0.1897 0.6114 0.112 Uiso 0.357(12) 1 calc PR B 1 H1C2 H 0.2199 0.1990 0.6633 0.112 Uiso 0.357(12) 1 calc PR B 1 H1C3 H 0.3656 0.1277 0.7064 0.112 Uiso 0.357(12) 1 calc PR B 1 C31B C 0.3993(15) 0.3070(9) 0.6946(7) 0.054(3) Uani 0.357(12) 1 d P B 1 H1B1 H 0.3053 0.3285 0.7390 0.065 Uiso 0.357(12) 1 calc PR B 1 H1B2 H 0.5082 0.2932 0.7176 0.065 Uiso 0.357(12) 1 calc PR B 1 C31A C 0.4311(17) 0.4056(10) 0.6223(7) 0.051(3) Uani 0.357(12) 1 d P B 1 H1A1 H 0.3186 0.4257 0.6038 0.061 Uiso 0.357(12) 1 calc PR B 1 H1A2 H 0.5138 0.3800 0.5753 0.061 Uiso 0.357(12) 1 calc PR B 1 C2C C 0.292(2) 0.2364(11) 0.6664(12) 0.111(5) Uani 0.643(12) 1 d P B 2 H2C1 H 0.3118 0.2008 0.7214 0.166 Uiso 0.643(12) 1 calc PR B 2 H2C2 H 0.3728 0.2032 0.6232 0.166 Uiso 0.643(12) 1 calc PR B 2 H2C3 H 0.1698 0.2199 0.6620 0.166 Uiso 0.643(12) 1 calc PR B 2 N1GA N 0.534(3) 0.5223(14) 0.6476(11) 0.048(4) Uani 0.643(12) 1 d P B 2 H5D H 0.875(5) 0.914(3) 0.506(2) 0.036(9) Uiso 1 1 d . . . H9D H 0.827(4) 0.970(3) 0.575(2) 0.033(8) Uiso 1 1 d . . . H12 H 0.787(5) 0.273(4) 0.763(2) 0.049(10) Uiso 1 1 d . . . O3A O 0.4941(3) 0.44690(18) 0.41897(13) 0.0401(5) Uani 1 1 d . . . H18 H 0.869(5) 0.169(2) 0.605(2) 0.046(10) Uiso 1 1 d D . . H23 H 0.825(7) 0.111(4) 0.6831(14) 0.084(15) Uiso 1 1 d D . . H2D H 0.822(4) 0.8419(14) 0.5791(18) 0.038(8) Uiso 1 1 d D . . H8 H 0.465(9) 0.582(4) 0.474(4) 0.11(2) Uiso 1 1 d D . . H13 H 0.342(3) 0.665(5) 0.503(4) 0.11(2) Uiso 1 1 d D . . H6A H 0.376(6) 0.448(4) 0.422(3) 0.059(11) Uiso 1 1 d . . . H5G H 0.452(6) 0.553(4) 0.691(3) 0.058(9) Uiso 1 1 d . . . H2G H 0.511(6) 0.568(4) 0.603(3) 0.058(9) Uiso 1 1 d . . . H19 H 1.013(8) -0.358(5) 0.558(4) 0.094(17) Uiso 1 1 d . . . H12D H 1.037(4) 0.762(2) 0.4379(18) 0.042(9) Uiso 1 1 d D . . H9G H 0.660(10) 0.532(6) 0.649(4) 0.12(2) Uiso 1 1 d . . . H6B H 0.182(3) 0.608(4) 0.771(3) 0.078(14) Uiso 1 1 d D . . O43A O 0.9662(19) 0.3869(11) 0.7007(7) 0.034(4) Uiso 0.172(9) 1 d P A 4 H5Y H 0.911(6) 0.403(4) 0.647(3) 0.036(10) Uiso 0.828(9) 1 d P A 3 H6Y H 0.898(7) 0.477(5) 0.701(3) 0.060(15) Uiso 0.828(9) 1 d P A 3 O5 O 0.6212(14) 0.2159(9) 0.4860(6) 0.065(2) Uiso 0.30 1 d PD . . H102 H 0.66(2) 0.233(14) 0.530(7) 0.084(15) Uiso 0.30 1 d PD . . H75 H 0.58(2) 0.284(8) 0.460(9) 0.084(15) Uiso 0.30 1 d PD . . H12C H 1.082(6) -0.431(4) 0.496(3) 0.072(13) Uiso 1 1 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 O12B 0.0376(10) 0.0210(8) 0.0214(8) -0.0009(7) -0.0018(7) -0.0028(7) O24B 0.0435(11) 0.0270(9) 0.0282(9) -0.0106(7) -0.0078(8) 0.0069(8) C9B 0.0224(11) 0.0210(10) 0.0222(10) -0.0071(8) -0.0042(8) -0.0001(8) C13B 0.0237(11) 0.0178(10) 0.0201(10) -0.0042(8) -0.0050(8) 0.0001(8) C17B 0.0271(12) 0.0192(10) 0.0197(10) -0.0039(8) -0.0045(9) -0.0005(8) C11B 0.0221(11) 0.0234(11) 0.0298(12) -0.0067(9) -0.0071(9) -0.0006(9) O13 0.0578(14) 0.0233(9) 0.0316(10) -0.0060(8) -0.0004(9) 0.0059(9) O24A 0.0509(12) 0.0250(9) 0.0428(11) -0.0105(8) -0.0200(9) 0.0128(8) C7B 0.0222(12) 0.0319(12) 0.0289(12) -0.0033(10) -0.0034(9) -0.0052(9) C12B 0.0215(11) 0.0202(10) 0.0242(11) -0.0041(8) -0.0021(9) -0.0007(8) C4B 0.0247(12) 0.0309(13) 0.0408(14) -0.0106(11) -0.0049(11) 0.0062(10) O3B 0.0362(12) 0.0424(11) 0.0411(11) 0.0023(9) -0.0049(9) 0.0107(9) C14B 0.0224(11) 0.0198(10) 0.0208(10) -0.0039(8) -0.0032(9) -0.0026(8) C10B 0.0261(12) 0.0258(11) 0.0313(12) -0.0132(9) -0.0070(10) 0.0019(9) C24B 0.0250(12) 0.0236(11) 0.0287(12) -0.0070(9) -0.0021(9) -0.0024(9) C5B 0.0262(13) 0.0306(13) 0.0339(13) -0.0114(10) -0.0023(10) 0.0059(10) C6B 0.0232(12) 0.0368(14) 0.0327(13) -0.0088(11) -0.0012(10) 0.0006(10) C8B 0.0220(11) 0.0237(10) 0.0211(10) -0.0053(8) -0.0027(8) -0.0025(8) C1B 0.0273(13) 0.0225(11) 0.0462(15) -0.0155(10) -0.0074(11) 0.0026(10) C23B 0.0346(13) 0.0218(11) 0.0252(12) -0.0064(9) -0.0060(10) 0.0012(9) C16B 0.0363(14) 0.0209(11) 0.0271(12) -0.0035(9) -0.0056(10) -0.0042(10) C2B 0.0269(13) 0.0250(12) 0.0426(15) -0.0051(11) -0.0024(11) 0.0004(10) C3B 0.0332(14) 0.0265(12) 0.0396(15) -0.0049(10) -0.0054(11) 0.0057(10) C18B 0.0324(13) 0.0268(11) 0.0243(11) -0.0064(9) -0.0094(10) 0.0025(10) C15B 0.0279(13) 0.0243(11) 0.0285(12) -0.0044(9) -0.0016(10) -0.0059(9) C20B 0.0317(13) 0.0245(11) 0.0285(12) -0.0084(9) -0.0110(10) 0.0071(10) C19B 0.0401(16) 0.0418(15) 0.0334(13) -0.0214(11) -0.0102(12) 0.0045(12) C22B 0.0362(14) 0.0235(11) 0.0293(12) -0.0071(9) -0.0101(10) 0.0067(10) C21B 0.0285(13) 0.0318(13) 0.0477(16) -0.0166(11) -0.0092(12) 0.0043(10) O12A 0.0346(10) 0.0208(8) 0.0213(8) -0.0018(6) -0.0020(7) 0.0044(7) O24D 0.0364(10) 0.0237(8) 0.0408(11) -0.0117(7) -0.0010(8) -0.0020(7) C13A 0.0224(11) 0.0192(10) 0.0194(10) -0.0049(8) -0.0003(8) 0.0007(8) C9A 0.0204(11) 0.0211(10) 0.0263(11) -0.0094(8) -0.0012(9) 0.0013(8) C11A 0.0218(11) 0.0196(10) 0.0286(12) -0.0063(9) -0.0027(9) 0.0025(8) C12A 0.0220(11) 0.0211(10) 0.0213(11) -0.0048(8) -0.0013(9) 0.0024(8) O24C 0.0598(14) 0.0344(10) 0.0343(11) -0.0124(8) 0.0111(9) -0.0052(9) C24A 0.0362(14) 0.0264(12) 0.0271(12) -0.0088(9) -0.0060(10) 0.0001(10) C17A 0.0275(12) 0.0189(10) 0.0187(10) -0.0033(8) -0.0001(9) 0.0001(9) C14A 0.0225(11) 0.0212(10) 0.0197(10) -0.0028(8) -0.0001(8) 0.0018(8) C5A 0.0295(13) 0.0328(13) 0.0361(14) -0.0153(11) -0.0074(11) -0.0016(10) C18A 0.0265(12) 0.0270(12) 0.0235(11) -0.0063(9) 0.0026(9) -0.0002(9) C8A 0.0233(11) 0.0239(11) 0.0221(11) -0.0067(8) -0.0025(9) 0.0024(9) C4A 0.0254(13) 0.0322(13) 0.0413(15) -0.0079(11) -0.0065(11) -0.0011(10) C10A 0.0253(12) 0.0272(12) 0.0371(13) -0.0165(10) -0.0037(10) 0.0013(9) C7A 0.0256(12) 0.0291(12) 0.0279(12) -0.0028(10) -0.0054(10) 0.0024(9) C20A 0.0293(12) 0.0241(11) 0.0256(12) -0.0076(9) 0.0029(9) -0.0046(9) C6A 0.0314(14) 0.0445(15) 0.0308(13) -0.0084(11) -0.0086(11) -0.0022(12) C16A 0.0350(14) 0.0219(11) 0.0302(12) -0.0046(9) -0.0033(10) 0.0058(10) C23A 0.0569(18) 0.0218(12) 0.0278(13) -0.0066(10) 0.0040(12) -0.0050(11) C22A 0.0361(14) 0.0205(11) 0.0302(12) -0.0085(9) 0.0017(10) -0.0043(10) C19A 0.0370(15) 0.0449(16) 0.0427(16) -0.0280(13) 0.0028(12) -0.0003(12) C2A 0.0326(14) 0.0227(12) 0.0544(17) -0.0082(11) -0.0131(12) 0.0009(10) C1A 0.0262(13) 0.0273(12) 0.0545(17) -0.0180(11) -0.0065(12) 0.0027(10) C3A 0.0326(14) 0.0282(13) 0.0419(15) -0.0079(11) -0.0048(11) -0.0042(11) C15A 0.0332(13) 0.0232(11) 0.0295(12) -0.0021(9) -0.0071(10) 0.0079(10) C21A 0.0302(14) 0.0358(14) 0.0513(17) -0.0204(12) -0.0095(12) 0.0026(11) N1G 0.0364(13) 0.0238(10) 0.0267(11) -0.0031(9) 0.0006(10) 0.0022(9) C1G 0.0406(16) 0.0365(14) 0.0350(14) -0.0068(11) -0.0063(12) 0.0043(12) C2G 0.0406(18) 0.065(2) 0.0458(18) -0.0117(15) 0.0015(14) 0.0014(15) C3G 0.041(2) 0.114(4) 0.075(3) -0.037(3) 0.0017(19) 0.003(2) O43 0.066(2) 0.0252(13) 0.0303(14) -0.0090(10) 0.0114(13) -0.0087(13) O49 0.0839(18) 0.0320(11) 0.0314(11) -0.0084(9) 0.0065(11) -0.0146(11) O57 0.0631(17) 0.0538(15) 0.0500(14) -0.0186(11) -0.0133(12) 0.0001(13) N1GB 0.058(14) 0.068(14) 0.043(11) 0.011(9) -0.009(8) 0.036(11) C32A 0.064(4) 0.060(4) 0.070(4) -0.015(3) -0.023(4) 0.017(3) C32B 0.072(5) 0.056(4) 0.059(4) -0.007(3) -0.016(3) -0.004(3) C1C 0.072(11) 0.034(8) 0.118(14) 0.001(8) -0.031(9) -0.010(7) C31B 0.055(6) 0.059(7) 0.052(6) -0.001(5) -0.024(5) -0.008(5) C31A 0.049(7) 0.059(6) 0.048(6) 0.005(5) -0.028(5) -0.016(5) C2C 0.139(13) 0.059(8) 0.144(11) 0.011(8) -0.071(10) -0.015(7) N1GA 0.044(5) 0.061(7) 0.039(6) -0.019(5) 0.000(4) -0.002(4) O3A 0.0339(12) 0.0410(11) 0.0435(12) -0.0030(9) -0.0054(9) -0.0050(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O12B C12B 1.426(3) . ? O12B H12 0.85(4) . ? O24B C24B 1.267(3) . ? C9B C11B 1.527(3) . ? C9B C8B 1.550(3) . ? C9B C10B 1.556(3) . ? C9B H7 1.0000 . ? C13B C18B 1.532(3) . ? C13B C12B 1.539(3) . ? C13B C14B 1.547(3) . ? C13B C17B 1.557(3) . ? C17B C20B 1.535(3) . ? C17B C16B 1.561(3) . ? C17B H9 1.0000 . ? C11B C12B 1.540(3) . ? C11B H10A 0.9900 . ? C11B H10B 0.9900 . ? O13 H19 0.91(6) . ? O13 H12C 0.87(5) . ? O24A C24B 1.243(3) . ? C7B C8B 1.527(3) . ? C7B C6B 1.530(4) . ? C7B H16A 0.9900 . ? C7B H16B 0.9900 . ? C12B H17 1.0000 . ? C4B C3B 1.526(4) . ? C4B C5B 1.542(4) . ? C4B H19A 0.9900 . ? C4B H19B 0.9900 . ? O3B C3B 1.427(3) . ? O3B H6B 0.941(15) . ? C14B C8B 1.522(3) . ? C14B C15B 1.531(3) . ? C14B H21 1.0000 . ? C10B C1B 1.540(4) . ? C10B C19B 1.546(4) . ? C10B C5B 1.553(4) . ? C24B C23B 1.526(3) . ? C5B C6B 1.537(4) . ? C5B H27 1.0000 . ? C6B H28A 0.9900 . ? C6B H28B 0.9900 . ? C8B H29 1.0000 . ? C1B C2B 1.516(4) . ? C1B H33A 0.9900 . ? C1B H33B 0.9900 . ? C23B C22B 1.521(3) . ? C23B H40A 0.9900 . ? C23B H40B 0.9900 . ? C16B C15B 1.539(4) . ? C16B H41A 0.9900 . ? C16B H41B 0.9900 . ? C2B C3B 1.516(4) . ? C2B H42A 0.9900 . ? C2B H42B 0.9900 . ? C3B H44 1.0000 . ? C18B H45A 0.9800 . ? C18B H45B 0.9800 . ? C18B H45C 0.9800 . ? C15B H46A 0.9900 . ? C15B H46B 0.9900 . ? C20B C21B 1.532(4) . ? C20B C22B 1.544(3) . ? C20B H47 1.0000 . ? C19B H48A 0.9800 . ? C19B H48B 0.9800 . ? C19B H48C 0.9800 . ? C22B H54A 0.9900 . ? C22B H54B 0.9900 . ? C21B H56A 0.9800 . ? C21B H56B 0.9800 . ? C21B H56C 0.9800 . ? O12A C12A 1.440(3) . ? O12A H12D 0.947(14) . ? O24D C24A 1.251(3) . ? C13A C12A 1.535(3) . ? C13A C18A 1.538(3) . ? C13A C14A 1.542(3) . ? C13A C17A 1.551(3) . ? C9A C11A 1.532(3) . ? C9A C8A 1.549(3) . ? C9A C10A 1.557(3) . ? C9A H6 1.0000 . ? C11A C12A 1.536(3) . ? C11A H12A 0.9900 . ? C11A H12B 0.9900 . ? C12A H15 1.0000 . ? O24C C24A 1.253(3) . ? C24A C23A 1.517(3) . ? C17A C20A 1.536(3) . ? C17A C16A 1.561(3) . ? C17A H17A 1.0000 . ? C14A C8A 1.527(3) . ? C14A C15A 1.535(3) . ? C14A H26 1.0000 . ? C5A C6A 1.536(4) . ? C5A C4A 1.540(4) . ? C5A C10A 1.556(4) . ? C5A H30 1.0000 . ? C18A H31A 0.9800 . ? C18A H31B 0.9800 . ? C18A H31C 0.9800 . ? C8A C7A 1.528(3) . ? C8A H32 1.0000 . ? C4A C3A 1.513(4) . ? C4A H34A 0.9900 . ? C4A H34B 0.9900 . ? C10A C19A 1.542(4) . ? C10A C1A 1.542(4) . ? C7A C6A 1.523(4) . ? C7A H36A 0.9900 . ? C7A H36B 0.9900 . ? C20A C22A 1.536(3) . ? C20A C21A 1.536(4) . ? C20A H38 1.0000 . ? C6A H39A 0.9900 . ? C6A H39B 0.9900 . ? C16A C15A 1.540(4) . ? C16A H50A 0.9900 . ? C16A H50B 0.9900 . ? C23A C22A 1.518(4) . ? C23A H51A 0.9900 . ? C23A H51B 0.9900 . ? C22A H52A 0.9900 . ? C22A H52B 0.9900 . ? C19A H53A 0.9800 . ? C19A H53B 0.9800 . ? C19A H53C 0.9800 . ? C2A C3A 1.511(4) . ? C2A C1A 1.517(4) . ? C2A H55A 0.9900 . ? C2A H55B 0.9900 . ? C1A H58A 0.9900 . ? C1A H58B 0.9900 . ? C3A O3A 1.432(4) . ? C3A H60B 1.01(4) . ? C15A H61A 0.9900 . ? C15A H61B 0.9900 . ? C21A H62A 0.9800 . ? C21A H62B 0.9800 . ? C21A H62C 0.9800 . ? N1G C1G 1.484(4) . ? N1G H5D 0.81(4) . ? N1G H9D 0.87(4) . ? N1G H2D 0.897(2) . ? C1G C2G 1.513(4) . ? C1G H59A 0.9900 . ? C1G H59B 0.9900 . ? C2G C3G 1.521(6) . ? C2G H64A 0.9900 . ? C2G H64B 0.9900 . ? C3G H65A 0.9800 . ? C3G H65B 0.9800 . ? C3G H65C 0.9800 . ? O43 H5Y 0.86(5) . ? O43 H6Y 0.83(6) . ? O49 H18 0.810(19) . ? O49 H23 0.82(2) . ? O57 H8 0.91(2) . ? O57 H13 0.91(2) . ? N1GB C31A 1.62(3) . ? N1GB H5G 0.91(5) . ? N1GB H2G 0.87(6) . ? N1GB H9G 1.16(8) . ? C32A N1GA 1.417(17) . ? C32A C32B 1.480(12) . ? C32A H2A1 0.9900 . ? C32A H2A2 0.9900 . ? C32B C2C 1.528(14) . ? C32B H2B1 0.9900 . ? C32B H2B2 0.9900 . ? C1C C31B 1.51(2) . ? C1C H1C1 0.9800 . ? C1C H1C2 0.9800 . ? C1C H1C3 0.9800 . ? C31B C31A 1.502(16) . ? C31B H1B1 0.9900 . ? C31B H1B2 0.9900 . ? C31A H1A1 0.9900 . ? C31A H1A2 0.9900 . ? C2C H2C1 0.9800 . ? C2C H2C2 0.9800 . ? C2C H2C3 0.9800 . ? N1GA H5G 0.98(5) . ? N1GA H2G 0.89(5) . ? N1GA H9G 0.99(8) . ? O3A H6A 0.90(5) . ? O43A H5Y 1.05(4) . ? O43A H6Y 1.16(6) . ? O5 H102 0.91(2) . ? O5 H75 0.91(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12B O12B H12 114(3) . . ? C11B C9B C8B 113.35(18) . . ? C11B C9B C10B 113.95(19) . . ? C8B C9B C10B 111.06(19) . . ? C11B C9B H7 105.9 . . ? C8B C9B H7 105.9 . . ? C10B C9B H7 105.9 . . ? C18B C13B C12B 109.39(19) . . ? C18B C13B C14B 112.23(19) . . ? C12B C13B C14B 107.95(18) . . ? C18B C13B C17B 109.90(18) . . ? C12B C13B C17B 116.53(18) . . ? C14B C13B C17B 100.62(18) . . ? C20B C17B C13B 117.98(19) . . ? C20B C17B C16B 112.84(19) . . ? C13B C17B C16B 103.05(18) . . ? C20B C17B H9 107.5 . . ? C13B C17B H9 107.5 . . ? C16B C17B H9 107.5 . . ? C9B C11B C12B 114.33(19) . . ? C9B C11B H10A 108.7 . . ? C12B C11B H10A 108.7 . . ? C9B C11B H10B 108.7 . . ? C12B C11B H10B 108.7 . . ? H10A C11B H10B 107.6 . . ? H19 O13 H12C 109(5) . . ? C8B C7B C6B 112.2(2) . . ? C8B C7B H16A 109.2 . . ? C6B C7B H16A 109.2 . . ? C8B C7B H16B 109.2 . . ? C6B C7B H16B 109.2 . . ? H16A C7B H16B 107.9 . . ? O12B C12B C13B 108.81(18) . . ? O12B C12B C11B 111.31(19) . . ? C13B C12B C11B 109.87(19) . . ? O12B C12B H17 108.9 . . ? C13B C12B H17 108.9 . . ? C11B C12B H17 108.9 . . ? C3B C4B C5B 113.1(2) . . ? C3B C4B H19A 109.0 . . ? C5B C4B H19A 109.0 . . ? C3B C4B H19B 109.0 . . ? C5B C4B H19B 109.0 . . ? H19A C4B H19B 107.8 . . ? C3B O3B H6B 114(3) . . ? C8B C14B C15B 118.02(19) . . ? C8B C14B C13B 114.00(18) . . ? C15B C14B C13B 103.42(18) . . ? C8B C14B H21 106.9 . . ? C15B C14B H21 106.9 . . ? C13B C14B H21 106.9 . . ? C1B C10B C19B 106.4(2) . . ? C1B C10B C5B 107.9(2) . . ? C19B C10B C5B 109.4(2) . . ? C1B C10B C9B 112.2(2) . . ? C19B C10B C9B 112.0(2) . . ? C5B C10B C9B 108.83(19) . . ? O24A C24B O24B 123.9(2) . . ? O24A C24B C23B 119.8(2) . . ? O24B C24B C23B 116.3(2) . . ? C6B C5B C4B 110.8(2) . . ? C6B C5B C10B 111.3(2) . . ? C4B C5B C10B 112.6(2) . . ? C6B C5B H27 107.3 . . ? C4B C5B H27 107.3 . . ? C10B C5B H27 107.3 . . ? C7B C6B C5B 112.5(2) . . ? C7B C6B H28A 109.1 . . ? C5B C6B H28A 109.1 . . ? C7B C6B H28B 109.1 . . ? C5B C6B H28B 109.1 . . ? H28A C6B H28B 107.8 . . ? C14B C8B C7B 112.08(19) . . ? C14B C8B C9B 109.65(18) . . ? C7B C8B C9B 109.56(19) . . ? C14B C8B H29 108.5 . . ? C7B C8B H29 108.5 . . ? C9B C8B H29 108.5 . . ? C2B C1B C10B 113.4(2) . . ? C2B C1B H33A 108.9 . . ? C10B C1B H33A 108.9 . . ? C2B C1B H33B 108.9 . . ? C10B C1B H33B 108.9 . . ? H33A C1B H33B 107.7 . . ? C22B C23B C24B 114.8(2) . . ? C22B C23B H40A 108.6 . . ? C24B C23B H40A 108.6 . . ? C22B C23B H40B 108.6 . . ? C24B C23B H40B 108.6 . . ? H40A C23B H40B 107.5 . . ? C15B C16B C17B 107.27(19) . . ? C15B C16B H41A 110.3 . . ? C17B C16B H41A 110.3 . . ? C15B C16B H41B 110.3 . . ? C17B C16B H41B 110.3 . . ? H41A C16B H41B 108.5 . . ? C1B C2B C3B 111.1(2) . . ? C1B C2B H42A 109.4 . . ? C3B C2B H42A 109.4 . . ? C1B C2B H42B 109.4 . . ? C3B C2B H42B 109.4 . . ? H42A C2B H42B 108.0 . . ? O3B C3B C2B 107.2(2) . . ? O3B C3B C4B 111.6(2) . . ? C2B C3B C4B 111.3(2) . . ? O3B C3B H44 108.9 . . ? C2B C3B H44 108.9 . . ? C4B C3B H44 108.9 . . ? C13B C18B H45A 109.5 . . ? C13B C18B H45B 109.5 . . ? H45A C18B H45B 109.5 . . ? C13B C18B H45C 109.5 . . ? H45A C18B H45C 109.5 . . ? H45B C18B H45C 109.5 . . ? C14B C15B C16B 104.02(19) . . ? C14B C15B H46A 111.0 . . ? C16B C15B H46A 111.0 . . ? C14B C15B H46B 111.0 . . ? C16B C15B H46B 111.0 . . ? H46A C15B H46B 109.0 . . ? C21B C20B C17B 113.1(2) . . ? C21B C20B C22B 109.9(2) . . ? C17B C20B C22B 111.7(2) . . ? C21B C20B H47 107.3 . . ? C17B C20B H47 107.3 . . ? C22B C20B H47 107.3 . . ? C10B C19B H48A 109.5 . . ? C10B C19B H48B 109.5 . . ? H48A C19B H48B 109.5 . . ? C10B C19B H48C 109.5 . . ? H48A C19B H48C 109.5 . . ? H48B C19B H48C 109.5 . . ? C23B C22B C20B 113.9(2) . . ? C23B C22B H54A 108.8 . . ? C20B C22B H54A 108.8 . . ? C23B C22B H54B 108.8 . . ? C20B C22B H54B 108.8 . . ? H54A C22B H54B 107.7 . . ? C20B C21B H56A 109.5 . . ? C20B C21B H56B 109.5 . . ? H56A C21B H56B 109.5 . . ? C20B C21B H56C 109.5 . . ? H56A C21B H56C 109.5 . . ? H56B C21B H56C 109.5 . . ? C12A O12A H12D 108(2) . . ? C12A C13A C18A 109.00(18) . . ? C12A C13A C14A 108.25(18) . . ? C18A C13A C14A 111.90(19) . . ? C12A C13A C17A 117.20(18) . . ? C18A C13A C17A 109.40(18) . . ? C14A C13A C17A 100.92(18) . . ? C11A C9A C8A 112.64(18) . . ? C11A C9A C10A 113.65(19) . . ? C8A C9A C10A 111.18(19) . . ? C11A C9A H6 106.3 . . ? C8A C9A H6 106.3 . . ? C10A C9A H6 106.3 . . ? C9A C11A C12A 114.56(19) . . ? C9A C11A H12A 108.6 . . ? C12A C11A H12A 108.6 . . ? C9A C11A H12B 108.6 . . ? C12A C11A H12B 108.6 . . ? H12A C11A H12B 107.6 . . ? O12A C12A C13A 108.78(18) . . ? O12A C12A C11A 110.63(18) . . ? C13A C12A C11A 110.91(19) . . ? O12A C12A H15 108.8 . . ? C13A C12A H15 108.8 . . ? C11A C12A H15 108.8 . . ? O24D C24A O24C 124.6(2) . . ? O24D C24A C23A 119.3(2) . . ? O24C C24A C23A 116.1(2) . . ? C20A C17A C13A 119.06(19) . . ? C20A C17A C16A 112.50(19) . . ? C13A C17A C16A 103.41(19) . . ? C20A C17A H17A 107.1 . . ? C13A C17A H17A 107.1 . . ? C16A C17A H17A 107.1 . . ? C8A C14A C15A 118.1(2) . . ? C8A C14A C13A 113.98(19) . . ? C15A C14A C13A 103.67(18) . . ? C8A C14A H26 106.8 . . ? C15A C14A H26 106.8 . . ? C13A C14A H26 106.8 . . ? C6A C5A C4A 110.1(2) . . ? C6A C5A C10A 111.7(2) . . ? C4A C5A C10A 112.3(2) . . ? C6A C5A H30 107.5 . . ? C4A C5A H30 107.5 . . ? C10A C5A H30 107.5 . . ? C13A C18A H31A 109.5 . . ? C13A C18A H31B 109.5 . . ? H31A C18A H31B 109.5 . . ? C13A C18A H31C 109.5 . . ? H31A C18A H31C 109.5 . . ? H31B C18A H31C 109.5 . . ? C14A C8A C7A 112.13(19) . . ? C14A C8A C9A 109.26(18) . . ? C7A C8A C9A 110.06(19) . . ? C14A C8A H32 108.4 . . ? C7A C8A H32 108.4 . . ? C9A C8A H32 108.4 . . ? C3A C4A C5A 113.5(2) . . ? C3A C4A H34A 108.9 . . ? C5A C4A H34A 108.9 . . ? C3A C4A H34B 108.9 . . ? C5A C4A H34B 108.9 . . ? H34A C4A H34B 107.7 . . ? C19A C10A C1A 106.8(2) . . ? C19A C10A C5A 109.4(2) . . ? C1A C10A C5A 107.7(2) . . ? C19A C10A C9A 111.4(2) . . ? C1A C10A C9A 112.0(2) . . ? C5A C10A C9A 109.51(19) . . ? C6A C7A C8A 111.9(2) . . ? C6A C7A H36A 109.2 . . ? C8A C7A H36A 109.2 . . ? C6A C7A H36B 109.2 . . ? C8A C7A H36B 109.2 . . ? H36A C7A H36B 107.9 . . ? C22A C20A C21A 110.1(2) . . ? C22A C20A C17A 111.7(2) . . ? C21A C20A C17A 113.1(2) . . ? C22A C20A H38 107.2 . . ? C21A C20A H38 107.2 . . ? C17A C20A H38 107.2 . . ? C7A C6A C5A 112.3(2) . . ? C7A C6A H39A 109.1 . . ? C5A C6A H39A 109.1 . . ? C7A C6A H39B 109.1 . . ? C5A C6A H39B 109.1 . . ? H39A C6A H39B 107.9 . . ? C15A C16A C17A 107.27(19) . . ? C15A C16A H50A 110.3 . . ? C17A C16A H50A 110.3 . . ? C15A C16A H50B 110.3 . . ? C17A C16A H50B 110.3 . . ? H50A C16A H50B 108.5 . . ? C24A C23A C22A 115.9(2) . . ? C24A C23A H51A 108.3 . . ? C22A C23A H51A 108.3 . . ? C24A C23A H51B 108.3 . . ? C22A C23A H51B 108.3 . . ? H51A C23A H51B 107.4 . . ? C23A C22A C20A 114.1(2) . . ? C23A C22A H52A 108.7 . . ? C20A C22A H52A 108.7 . . ? C23A C22A H52B 108.7 . . ? C20A C22A H52B 108.7 . . ? H52A C22A H52B 107.6 . . ? C10A C19A H53A 109.5 . . ? C10A C19A H53B 109.5 . . ? H53A C19A H53B 109.5 . . ? C10A C19A H53C 109.5 . . ? H53A C19A H53C 109.5 . . ? H53B C19A H53C 109.5 . . ? C3A C2A C1A 110.5(2) . . ? C3A C2A H55A 109.6 . . ? C1A C2A H55A 109.6 . . ? C3A C2A H55B 109.6 . . ? C1A C2A H55B 109.6 . . ? H55A C2A H55B 108.1 . . ? C2A C1A C10A 113.8(2) . . ? C2A C1A H58A 108.8 . . ? C10A C1A H58A 108.8 . . ? C2A C1A H58B 108.8 . . ? C10A C1A H58B 108.8 . . ? H58A C1A H58B 107.7 . . ? O3A C3A C2A 106.9(2) . . ? O3A C3A C4A 111.1(2) . . ? C2A C3A C4A 111.7(2) . . ? O3A C3A H60B 109.1(19) . . ? C2A C3A H60B 109.3(19) . . ? C4A C3A H60B 108.7(18) . . ? C14A C15A C16A 103.7(2) . . ? C14A C15A H61A 111.0 . . ? C16A C15A H61A 111.0 . . ? C14A C15A H61B 111.0 . . ? C16A C15A H61B 111.0 . . ? H61A C15A H61B 109.0 . . ? C20A C21A H62A 109.5 . . ? C20A C21A H62B 109.5 . . ? H62A C21A H62B 109.5 . . ? C20A C21A H62C 109.5 . . ? H62A C21A H62C 109.5 . . ? H62B C21A H62C 109.5 . . ? C1G N1G H5D 109(2) . . ? C1G N1G H9D 111(2) . . ? H5D N1G H9D 111(3) . . ? C1G N1G H2D 109(2) . . ? H5D N1G H2D 104(3) . . ? H9D N1G H2D 112(3) . . ? N1G C1G C2G 110.2(3) . . ? N1G C1G H59A 109.6 . . ? C2G C1G H59A 109.6 . . ? N1G C1G H59B 109.6 . . ? C2G C1G H59B 109.6 . . ? H59A C1G H59B 108.1 . . ? C1G C2G C3G 111.8(3) . . ? C1G C2G H64A 109.3 . . ? C3G C2G H64A 109.3 . . ? C1G C2G H64B 109.3 . . ? C3G C2G H64B 109.3 . . ? H64A C2G H64B 107.9 . . ? C2G C3G H65A 109.5 . . ? C2G C3G H65B 109.5 . . ? H65A C3G H65B 109.5 . . ? C2G C3G H65C 109.5 . . ? H65A C3G H65C 109.5 . . ? H65B C3G H65C 109.5 . . ? H5Y O43 H6Y 103(4) . . ? H18 O49 H23 111(5) . . ? H8 O57 H13 103(6) . . ? C31A N1GB H5G 120(4) . . ? C31A N1GB H2G 98(4) . . ? H5G N1GB H2G 108(4) . . ? C31A N1GB H9G 123(4) . . ? H5G N1GB H9G 107(6) . . ? H2G N1GB H9G 97(5) . . ? N1GA C32A C32B 110.9(9) . . ? N1GA C32A H2A1 109.5 . . ? C32B C32A H2A1 109.5 . . ? N1GA C32A H2A2 109.5 . . ? C32B C32A H2A2 109.5 . . ? H2A1 C32A H2A2 108.0 . . ? C32A C32B C2C 111.7(8) . . ? C32A C32B H2B1 109.3 . . ? C2C C32B H2B1 109.3 . . ? C32A C32B H2B2 109.3 . . ? C2C C32B H2B2 109.3 . . ? H2B1 C32B H2B2 107.9 . . ? C31A C31B C1C 110.0(12) . . ? C31A C31B H1B1 109.7 . . ? C1C C31B H1B1 109.7 . . ? C31A C31B H1B2 109.7 . . ? C1C C31B H1B2 109.7 . . ? H1B1 C31B H1B2 108.2 . . ? C31B C31A N1GB 110.8(14) . . ? C31B C31A H1A1 109.5 . . ? N1GB C31A H1A1 109.5 . . ? C31B C31A H1A2 109.5 . . ? N1GB C31A H1A2 109.5 . . ? H1A1 C31A H1A2 108.1 . . ? C32B C2C H2C1 109.5 . . ? C32B C2C H2C2 109.5 . . ? H2C1 C2C H2C2 109.5 . . ? C32B C2C H2C3 109.5 . . ? H2C1 C2C H2C3 109.5 . . ? H2C2 C2C H2C3 109.5 . . ? C32A N1GA H5G 110(3) . . ? C32A N1GA H2G 119(3) . . ? H5G N1GA H2G 101(4) . . ? C32A N1GA H9G 104(4) . . ? H5G N1GA H9G 115(5) . . ? H2G N1GA H9G 108(5) . . ? C3A O3A H6A 116(3) . . ? H5Y O43A H6Y 74(3) . . ? H102 O5 H75 108(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C18B C13B C17B C20B -45.7(3) . . . . ? C12B C13B C17B C20B 79.4(3) . . . . ? C14B C13B C17B C20B -164.23(19) . . . . ? C18B C13B C17B C16B 79.3(2) . . . . ? C12B C13B C17B C16B -155.5(2) . . . . ? C14B C13B C17B C16B -39.2(2) . . . . ? C8B C9B C11B C12B 49.2(3) . . . . ? C10B C9B C11B C12B 177.5(2) . . . . ? C18B C13B C12B O12B 173.22(18) . . . . ? C14B C13B C12B O12B -64.4(2) . . . . ? C17B C13B C12B O12B 47.8(3) . . . . ? C18B C13B C12B C11B -64.7(2) . . . . ? C14B C13B C12B C11B 57.7(2) . . . . ? C17B C13B C12B C11B 169.92(19) . . . . ? C9B C11B C12B O12B 66.4(2) . . . . ? C9B C11B C12B C13B -54.2(3) . . . . ? C18B C13B C14B C8B 59.4(2) . . . . ? C12B C13B C14B C8B -61.3(2) . . . . ? C17B C13B C14B C8B 176.16(18) . . . . ? C18B C13B C14B C15B -70.0(2) . . . . ? C12B C13B C14B C15B 169.34(18) . . . . ? C17B C13B C14B C15B 46.8(2) . . . . ? C11B C9B C10B C1B 52.0(3) . . . . ? C8B C9B C10B C1B -178.51(19) . . . . ? C11B C9B C10B C19B -67.6(3) . . . . ? C8B C9B C10B C19B 61.9(3) . . . . ? C11B C9B C10B C5B 171.31(19) . . . . ? C8B C9B C10B C5B -59.2(2) . . . . ? C3B C4B C5B C6B -177.6(2) . . . . ? C3B C4B C5B C10B -52.3(3) . . . . ? C1B C10B C5B C6B 177.8(2) . . . . ? C19B C10B C5B C6B -66.8(3) . . . . ? C9B C10B C5B C6B 55.9(3) . . . . ? C1B C10B C5B C4B 52.7(3) . . . . ? C19B C10B C5B C4B 168.2(2) . . . . ? C9B C10B C5B C4B -69.2(3) . . . . ? C8B C7B C6B C5B 53.7(3) . . . . ? C4B C5B C6B C7B 72.3(3) . . . . ? C10B C5B C6B C7B -53.8(3) . . . . ? C15B C14B C8B C7B -61.1(3) . . . . ? C13B C14B C8B C7B 177.26(18) . . . . ? C15B C14B C8B C9B 177.0(2) . . . . ? C13B C14B C8B C9B 55.4(2) . . . . ? C6B C7B C8B C14B -177.4(2) . . . . ? C6B C7B C8B C9B -55.4(3) . . . . ? C11B C9B C8B C14B -47.8(2) . . . . ? C10B C9B C8B C14B -177.56(19) . . . . ? C11B C9B C8B C7B -171.17(19) . . . . ? C10B C9B C8B C7B 59.0(2) . . . . ? C19B C10B C1B C2B -174.1(2) . . . . ? C5B C10B C1B C2B -56.8(3) . . . . ? C9B C10B C1B C2B 63.1(3) . . . . ? O24A C24B C23B C22B -7.3(4) . . . . ? O24B C24B C23B C22B 171.3(2) . . . . ? C20B C17B C16B C15B 146.5(2) . . . . ? C13B C17B C16B C15B 18.2(2) . . . . ? C10B C1B C2B C3B 58.7(3) . . . . ? C1B C2B C3B O3B -176.4(2) . . . . ? C1B C2B C3B C4B -54.1(3) . . . . ? C5B C4B C3B O3B 171.4(2) . . . . ? C5B C4B C3B C2B 51.7(3) . . . . ? C8B C14B C15B C16B -162.4(2) . . . . ? C13B C14B C15B C16B -35.5(2) . . . . ? C17B C16B C15B C14B 10.4(2) . . . . ? C13B C17B C20B C21B -61.8(3) . . . . ? C16B C17B C20B C21B 178.1(2) . . . . ? C13B C17B C20B C22B 173.59(19) . . . . ? C16B C17B C20B C22B 53.5(3) . . . . ? C24B C23B C22B C20B 169.2(2) . . . . ? C21B C20B C22B C23B -69.9(3) . . . . ? C17B C20B C22B C23B 56.4(3) . . . . ? C8A C9A C11A C12A 49.5(3) . . . . ? C10A C9A C11A C12A 177.1(2) . . . . ? C18A C13A C12A O12A 171.81(19) . . . . ? C14A C13A C12A O12A -66.3(2) . . . . ? C17A C13A C12A O12A 46.9(3) . . . . ? C18A C13A C12A C11A -66.3(2) . . . . ? C14A C13A C12A C11A 55.6(2) . . . . ? C17A C13A C12A C11A 168.80(19) . . . . ? C9A C11A C12A O12A 68.1(2) . . . . ? C9A C11A C12A C13A -52.7(3) . . . . ? C12A C13A C17A C20A 78.8(3) . . . . ? C18A C13A C17A C20A -45.9(3) . . . . ? C14A C13A C17A C20A -163.93(19) . . . . ? C12A C13A C17A C16A -155.5(2) . . . . ? C18A C13A C17A C16A 79.8(2) . . . . ? C14A C13A C17A C16A -38.3(2) . . . . ? C12A C13A C14A C8A -60.5(2) . . . . ? C18A C13A C14A C8A 59.7(2) . . . . ? C17A C13A C14A C8A 175.90(18) . . . . ? C12A C13A C14A C15A 169.86(18) . . . . ? C18A C13A C14A C15A -70.0(2) . . . . ? C17A C13A C14A C15A 46.2(2) . . . . ? C15A C14A C8A C7A -58.7(3) . . . . ? C13A C14A C8A C7A 179.26(18) . . . . ? C15A C14A C8A C9A 179.0(2) . . . . ? C13A C14A C8A C9A 57.0(2) . . . . ? C11A C9A C8A C14A -49.6(2) . . . . ? C10A C9A C8A C14A -178.49(19) . . . . ? C11A C9A C8A C7A -173.14(19) . . . . ? C10A C9A C8A C7A 58.0(2) . . . . ? C6A C5A C4A C3A -177.4(2) . . . . ? C10A C5A C4A C3A -52.3(3) . . . . ? C6A C5A C10A C19A -67.9(3) . . . . ? C4A C5A C10A C19A 167.8(2) . . . . ? C6A C5A C10A C1A 176.4(2) . . . . ? C4A C5A C10A C1A 52.1(3) . . . . ? C6A C5A C10A C9A 54.4(3) . . . . ? C4A C5A C10A C9A -69.9(3) . . . . ? C11A C9A C10A C19A -64.0(3) . . . . ? C8A C9A C10A C19A 64.3(3) . . . . ? C11A C9A C10A C1A 55.5(3) . . . . ? C8A C9A C10A C1A -176.21(19) . . . . ? C11A C9A C10A C5A 174.8(2) . . . . ? C8A C9A C10A C5A -56.8(3) . . . . ? C14A C8A C7A C6A -178.2(2) . . . . ? C9A C8A C7A C6A -56.4(3) . . . . ? C13A C17A C20A C22A 176.0(2) . . . . ? C16A C17A C20A C22A 54.9(3) . . . . ? C13A C17A C20A C21A -59.1(3) . . . . ? C16A C17A C20A C21A 179.7(2) . . . . ? C8A C7A C6A C5A 54.9(3) . . . . ? C4A C5A C6A C7A 71.5(3) . . . . ? C10A C5A C6A C7A -54.0(3) . . . . ? C20A C17A C16A C15A 147.0(2) . . . . ? C13A C17A C16A C15A 17.2(2) . . . . ? O24D C24A C23A C22A -17.1(4) . . . . ? O24C C24A C23A C22A 162.6(3) . . . . ? C24A C23A C22A C20A -178.5(2) . . . . ? C21A C20A C22A C23A -64.6(3) . . . . ? C17A C20A C22A C23A 62.0(3) . . . . ? C3A C2A C1A C10A 58.6(3) . . . . ? C19A C10A C1A C2A -173.9(2) . . . . ? C5A C10A C1A C2A -56.6(3) . . . . ? C9A C10A C1A C2A 63.9(3) . . . . ? C1A C2A C3A O3A -176.0(2) . . . . ? C1A C2A C3A C4A -54.3(3) . . . . ? C5A C4A C3A O3A 171.7(2) . . . . ? C5A C4A C3A C2A 52.4(3) . . . . ? C8A C14A C15A C16A -162.6(2) . . . . ? C13A C14A C15A C16A -35.5(2) . . . . ? C17A C16A C15A C14A 11.0(3) . . . . ? N1G C1G C2G C3G 179.4(3) . . . . ? N1GA C32A C32B C2C -177.1(12) . . . . ? C1C C31B C31A N1GB -172.9(17) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.38 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.308 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.039 _chemical_name_common 'di-(propylammonium deoxycholate) hydrate' data_3 _database_code_depnum_ccdc_archive 'CCDC 886460' #TrackingRef 'REVISED_CIF_DATA_OCT_2012.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; di-n-butylammonium deoxycholate ; _chemical_formula_moiety ? _chemical_formula_sum 'C32 H59 N O4' _chemical_formula_weight 521.80 _chemical_absolute_configuration rm loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 14.043(3) _cell_length_b 7.8258(16) _cell_length_c 14.055(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.94(3) _cell_angle_gamma 90.00 _cell_volume 1516.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7058 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 28.29 _exptl_crystal_description rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.143 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 580 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type none _exptl_special_details ; none ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '1\% \f scans and \w scans' _diffrn_reflns_number 7058 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 28.29 _reflns_number_total 4023 _reflns_number_gt 3140 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0618P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 4023 _refine_ls_number_parameters 346 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1028 _refine_ls_wR_factor_gt 0.0941 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.35834(14) 0.4458(2) 0.60357(14) 0.0213(4) Uani 1 1 d . . . H2A H -0.4246 0.4479 0.6181 0.026 Uiso 1 1 calc R . . H2B H -0.3232 0.5468 0.6350 0.026 Uiso 1 1 calc R . . H1 H 0.4767 -0.0866 0.8976 0.034(6) Uiso 1 1 d R . . C2 C -0.36536(14) 0.4599(3) 0.49436(14) 0.0233(4) Uani 1 1 d . . . H11A H -0.3999 0.5664 0.4706 0.028 Uiso 1 1 calc R . . H11B H -0.2994 0.4652 0.4792 0.028 Uiso 1 1 calc R . . H2 H 0.5016 -0.1876 0.9898 0.044(6) Uiso 1 1 d R . . O3 O -0.42026(12) 0.3053(2) 0.34149(10) 0.0407(4) Uani 1 1 d D . . C3 C -0.41917(14) 0.3074(3) 0.44358(13) 0.0268(4) Uani 1 1 d . . . H14 H -0.4876 0.3100 0.4541 0.032 Uiso 1 1 calc R . . C4 C -0.37233(15) 0.1408(3) 0.48439(14) 0.0236(4) Uani 1 1 d . . . H15A H -0.3080 0.1304 0.4659 0.028 Uiso 1 1 calc R . . H15B H -0.4127 0.0441 0.4544 0.028 Uiso 1 1 calc R . . C5 C -0.35958(13) 0.1263(2) 0.59486(14) 0.0212(4) Uani 1 1 d . . . H5 H -0.4260 0.1236 0.6108 0.025 Uiso 1 1 calc R . . C6 C -0.30931(14) -0.0418(3) 0.63182(16) 0.0262(4) Uani 1 1 d . . . H17A H -0.3164 -0.0601 0.6998 0.031 Uiso 1 1 calc R . . H17B H -0.3421 -0.1377 0.5927 0.031 Uiso 1 1 calc R . . C7 C -0.20142(14) -0.0441(3) 0.62677(16) 0.0262(4) Uani 1 1 d . . . H10A H -0.1716 -0.1489 0.6589 0.031 Uiso 1 1 calc R . . H10B H -0.1947 -0.0485 0.5580 0.031 Uiso 1 1 calc R . . C8 C -0.14645(13) 0.1116(2) 0.67474(14) 0.0196(4) Uani 1 1 d . . . H4 H -0.1438 0.1053 0.7463 0.023 Uiso 1 1 calc R . . C9 C -0.19798(12) 0.2786(2) 0.63597(13) 0.0176(4) Uani 1 1 d . . . H6 H -0.1988 0.2803 0.5647 0.021 Uiso 1 1 calc R . . C10 C -0.30631(12) 0.2827(2) 0.64787(13) 0.0187(4) Uani 1 1 d . . . C11 C -0.13976(14) 0.4351(3) 0.67801(16) 0.0257(5) Uani 1 1 d . . . H7A H -0.1382 0.4395 0.7487 0.031 Uiso 1 1 calc R . . H7B H -0.1731 0.5394 0.6489 0.031 Uiso 1 1 calc R . . O12 O -0.04021(11) 0.4540(2) 0.55866(11) 0.0402(4) Uani 1 1 d . . . H12 H 0.0156 0.4721 0.5475 0.048 Uiso 1 1 calc R . . C12 C -0.03507(14) 0.4352(2) 0.66013(15) 0.0241(4) Uani 1 1 d . . . H8 H 0.0002 0.5355 0.6941 0.029 Uiso 1 1 calc R . . C13 C 0.01810(13) 0.2714(2) 0.69885(13) 0.0189(4) Uani 1 1 d . . . C14 C -0.04289(13) 0.1161(2) 0.65555(14) 0.0195(4) Uani 1 1 d . . . H3 H -0.0493 0.1262 0.5837 0.023 Uiso 1 1 calc R . . C15 C 0.02304(15) -0.0377(3) 0.68547(17) 0.0289(5) Uani 1 1 d . . . H20A H 0.0066 -0.1331 0.6390 0.035 Uiso 1 1 calc R . . H20B H 0.0179 -0.0779 0.7511 0.035 Uiso 1 1 calc R . . C16 C 0.12601(15) 0.0325(3) 0.68387(17) 0.0290(5) Uani 1 1 d . . . H33A H 0.1533 -0.0230 0.6317 0.035 Uiso 1 1 calc R . . H33B H 0.1698 0.0100 0.7465 0.035 Uiso 1 1 calc R . . C17 C 0.11525(14) 0.2285(2) 0.66542(14) 0.0208(4) Uani 1 1 d . . . H28 H 0.1031 0.2448 0.5936 0.025 Uiso 1 1 calc R . . C18 C 0.03526(14) 0.2738(3) 0.81031(13) 0.0282(5) Uani 1 1 d . . . H19A H -0.0271 0.2658 0.8316 0.042 Uiso 1 1 calc R . . H19B H 0.0677 0.3805 0.8343 0.042 Uiso 1 1 calc R . . H19C H 0.0762 0.1766 0.8360 0.042 Uiso 1 1 calc R . . C19 C -0.31490(14) 0.2789(3) 0.75521(14) 0.0279(4) Uani 1 1 d . . . H23A H -0.2872 0.3840 0.7870 0.042 Uiso 1 1 calc R . . H23B H -0.2795 0.1799 0.7868 0.042 Uiso 1 1 calc R . . H23C H -0.3834 0.2705 0.7603 0.042 Uiso 1 1 calc R . . C20 C 0.20747(13) 0.3309(3) 0.70690(13) 0.0223(4) Uani 1 1 d . . . H26 H 0.2229 0.3137 0.7787 0.027 Uiso 1 1 calc R . . C21 C 0.19464(15) 0.5221(3) 0.68653(17) 0.0293(5) Uani 1 1 d . . . H34A H 0.2575 0.5797 0.7046 0.044 Uiso 1 1 calc R . . H34B H 0.1491 0.5694 0.7246 0.044 Uiso 1 1 calc R . . H34C H 0.1691 0.5400 0.6174 0.044 Uiso 1 1 calc R . . C22 C 0.29304(12) 0.2636(3) 0.66358(13) 0.0217(4) Uani 1 1 d . . . H29A H 0.2922 0.1372 0.6658 0.026 Uiso 1 1 calc R . . H29B H 0.2827 0.2977 0.5945 0.026 Uiso 1 1 calc R . . C23 C 0.39351(12) 0.3247(3) 0.71319(13) 0.0210(4) Uani 1 1 d . . . H25A H 0.4392 0.3100 0.6681 0.025 Uiso 1 1 calc R . . H25B H 0.3903 0.4481 0.7278 0.025 Uiso 1 1 calc R . . C24 C 0.43213(13) 0.2287(3) 0.80656(14) 0.0225(4) Uani 1 1 d . . . O24A O 0.44761(13) 0.0720(2) 0.79917(11) 0.0404(4) Uani 1 1 d . . . H3B H -0.425(2) 0.4239(5) 0.3212(3) 0.080(10) Uiso 1 1 d D . . O24B O 0.44782(13) 0.3096(2) 0.88373(10) 0.0461(4) Uani 1 1 d . . . N1G N 0.48194(12) -0.1893(2) 0.92302(11) 0.0267(4) Uani 1 1 d . . . C1G C 0.38493(16) -0.2702(3) 0.89774(15) 0.0308(5) Uani 1 1 d . . . H27A H 0.3904 -0.3933 0.9140 0.037 Uiso 1 1 calc R . . H27B H 0.3605 -0.2596 0.8271 0.037 Uiso 1 1 calc R . . C2G C 0.31351(15) -0.1866(3) 0.95224(15) 0.0329(5) Uani 1 1 d . . . H31A H 0.3089 -0.0632 0.9365 0.040 Uiso 1 1 calc R . . H31B H 0.3380 -0.1980 1.0228 0.040 Uiso 1 1 calc R . . C3G C 0.21299(17) -0.2665(3) 0.92664(17) 0.0404(6) Uani 1 1 d . . . H35A H 0.1886 -0.2526 0.8562 0.049 Uiso 1 1 calc R . . H35B H 0.2186 -0.3905 0.9404 0.049 Uiso 1 1 calc R . . C4G C 0.13952(17) -0.1913(5) 0.98069(17) 0.0524(7) Uani 1 1 d . . . H37A H 0.1615 -0.2087 1.0505 0.079 Uiso 1 1 calc R . . H37B H 0.0768 -0.2479 0.9597 0.079 Uiso 1 1 calc R . . H37C H 0.1326 -0.0687 0.9669 0.079 Uiso 1 1 calc R . . C5G C 0.55910(16) -0.2776(3) 0.88244(15) 0.0293(5) Uani 1 1 d . . . H21A H 0.5414 -0.2790 0.8108 0.035 Uiso 1 1 calc R . . H21B H 0.5649 -0.3974 0.9055 0.035 Uiso 1 1 calc R . . C6G C 0.65554(16) -0.1869(3) 0.91350(15) 0.0319(5) Uani 1 1 d . . . H24A H 0.6707 -0.1791 0.9851 0.038 Uiso 1 1 calc R . . H24B H 0.6503 -0.0691 0.8873 0.038 Uiso 1 1 calc R . . C7G C 0.73796(17) -0.2793(3) 0.87839(17) 0.0351(5) Uani 1 1 d . . . H32A H 0.7429 -0.3970 0.9047 0.042 Uiso 1 1 calc R . . H32B H 0.7223 -0.2876 0.8068 0.042 Uiso 1 1 calc R . . C8G C 0.83534(18) -0.1912(4) 0.90808(18) 0.0494(6) Uani 1 1 d . . . H36A H 0.8316 -0.0755 0.8808 0.074 Uiso 1 1 calc R . . H36B H 0.8852 -0.2564 0.8837 0.074 Uiso 1 1 calc R . . H36C H 0.8521 -0.1846 0.9789 0.074 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0169(10) 0.0219(9) 0.0246(11) -0.0017(8) 0.0029(8) 0.0021(8) C2 0.0213(10) 0.0233(9) 0.0258(11) 0.0043(9) 0.0059(8) 0.0052(8) O3 0.0593(11) 0.0377(9) 0.0212(7) 0.0014(7) -0.0023(7) 0.0090(9) C3 0.0232(10) 0.0328(11) 0.0225(10) -0.0003(10) -0.0002(8) 0.0031(9) C4 0.0216(11) 0.0222(9) 0.0249(11) -0.0026(9) -0.0014(8) 0.0002(8) C5 0.0132(9) 0.0224(9) 0.0276(11) 0.0012(9) 0.0029(8) -0.0026(8) C6 0.0244(11) 0.0180(9) 0.0346(12) 0.0037(9) 0.0018(9) -0.0053(8) C7 0.0226(10) 0.0158(9) 0.0375(12) 0.0026(9) -0.0009(9) -0.0018(8) C8 0.0168(10) 0.0174(9) 0.0233(10) 0.0036(8) 0.0007(8) -0.0013(8) C9 0.0155(8) 0.0166(8) 0.0205(9) 0.0007(8) 0.0029(7) -0.0006(7) C10 0.0146(8) 0.0206(9) 0.0206(9) 0.0023(8) 0.0023(7) 0.0007(8) C11 0.0174(10) 0.0166(9) 0.0422(13) -0.0046(9) 0.0037(9) 0.0005(8) O12 0.0305(8) 0.0498(10) 0.0397(9) 0.0217(8) 0.0051(7) -0.0044(8) C12 0.0199(10) 0.0172(9) 0.0349(12) -0.0009(9) 0.0049(9) -0.0021(8) C13 0.0159(9) 0.0204(9) 0.0204(9) 0.0007(8) 0.0037(7) -0.0006(8) C14 0.0186(10) 0.0176(9) 0.0218(10) -0.0003(8) 0.0024(8) -0.0013(8) C15 0.0218(10) 0.0194(9) 0.0434(13) 0.0030(9) 0.0012(9) 0.0016(8) C16 0.0206(11) 0.0246(10) 0.0403(13) 0.0020(9) 0.0017(9) 0.0038(8) C17 0.0179(9) 0.0234(9) 0.0213(10) -0.0005(8) 0.0037(8) 0.0004(8) C18 0.0244(10) 0.0398(12) 0.0208(9) -0.0018(10) 0.0053(8) -0.0049(9) C19 0.0240(10) 0.0361(11) 0.0244(10) 0.0015(9) 0.0063(8) -0.0002(9) C20 0.0179(9) 0.0287(10) 0.0196(9) -0.0039(8) 0.0022(7) -0.0001(8) C21 0.0206(10) 0.0271(10) 0.0399(13) -0.0085(9) 0.0051(9) -0.0043(8) C22 0.0166(9) 0.0287(10) 0.0195(9) -0.0014(8) 0.0024(7) 0.0023(8) C23 0.0164(9) 0.0249(9) 0.0218(9) 0.0000(8) 0.0040(7) -0.0002(8) C24 0.0168(9) 0.0277(10) 0.0229(11) 0.0018(9) 0.0032(8) -0.0022(8) O24A 0.0584(11) 0.0285(8) 0.0306(9) 0.0060(7) -0.0007(7) 0.0057(7) O24B 0.0688(12) 0.0441(10) 0.0209(8) -0.0039(8) -0.0031(7) 0.0099(9) N1G 0.0343(10) 0.0239(9) 0.0202(8) 0.0024(8) 0.0005(7) 0.0007(8) C1G 0.0386(13) 0.0243(10) 0.0279(11) -0.0024(9) 0.0025(9) -0.0049(9) C2G 0.0357(12) 0.0349(11) 0.0271(11) -0.0023(10) 0.0033(9) -0.0034(10) C3G 0.0401(13) 0.0427(13) 0.0369(13) -0.0019(11) 0.0032(10) -0.0071(11) C4G 0.0373(13) 0.0768(19) 0.0418(14) -0.0046(16) 0.0041(11) -0.0060(15) C5G 0.0377(12) 0.0236(10) 0.0256(11) -0.0006(9) 0.0037(9) 0.0034(9) C6G 0.0422(12) 0.0290(11) 0.0249(10) 0.0006(10) 0.0071(9) 0.0001(10) C7G 0.0413(13) 0.0342(12) 0.0291(11) 0.0031(10) 0.0053(10) 0.0051(10) C8G 0.0412(14) 0.0626(17) 0.0450(14) 0.0070(15) 0.0098(11) -0.0002(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.523(3) . ? C1 C10 1.542(3) . ? C1 H2A 0.9900 . ? C1 H2B 0.9900 . ? C2 C3 1.517(3) . ? C2 H11A 0.9900 . ? C2 H11B 0.9900 . ? O3 C3 1.432(2) . ? O3 H3B 0.969(2) . ? C3 C4 1.523(3) . ? C3 H14 1.0000 . ? C4 C5 1.533(3) . ? C4 H15A 0.9900 . ? C4 H15B 0.9900 . ? C5 C6 1.537(3) . ? C5 C10 1.550(3) . ? C5 H5 1.0000 . ? C6 C7 1.530(3) . ? C6 H17A 0.9900 . ? C6 H17B 0.9900 . ? C7 C8 1.529(3) . ? C7 H10A 0.9900 . ? C7 H10B 0.9900 . ? C8 C14 1.529(3) . ? C8 C9 1.542(2) . ? C8 H4 1.0000 . ? C9 C11 1.528(3) . ? C9 C10 1.562(2) . ? C9 H6 1.0000 . ? C10 C19 1.536(3) . ? C11 C12 1.538(3) . ? C11 H7A 0.9900 . ? C11 H7B 0.9900 . ? O12 C12 1.422(3) . ? O12 H12 0.8400 . ? C12 C13 1.530(3) . ? C12 H8 1.0000 . ? C13 C18 1.539(3) . ? C13 C14 1.544(3) . ? C13 C17 1.561(3) . ? C14 C15 1.528(3) . ? C14 H3 1.0000 . ? C15 C16 1.551(3) . ? C15 H20A 0.9900 . ? C15 H20B 0.9900 . ? C16 C17 1.558(3) . ? C16 H33A 0.9900 . ? C16 H33B 0.9900 . ? C17 C20 1.540(3) . ? C17 H28 1.0000 . ? C18 H19A 0.9800 . ? C18 H19B 0.9800 . ? C18 H19C 0.9800 . ? C19 H23A 0.9800 . ? C19 H23B 0.9800 . ? C19 H23C 0.9800 . ? C20 C21 1.528(3) . ? C20 C22 1.539(2) . ? C20 H26 1.0000 . ? C21 H34A 0.9800 . ? C21 H34B 0.9800 . ? C21 H34C 0.9800 . ? C22 C23 1.527(3) . ? C22 H29A 0.9900 . ? C22 H29B 0.9900 . ? C23 C24 1.520(3) . ? C23 H25A 0.9900 . ? C23 H25B 0.9900 . ? C24 O24B 1.239(2) . ? C24 O24A 1.254(3) . ? N1G C1G 1.483(3) . ? N1G C5G 1.487(3) . ? N1G H1 0.8770 . ? N1G H2 0.9263 . ? C1G C2G 1.521(3) . ? C1G H27A 0.9900 . ? C1G H27B 0.9900 . ? C2G C3G 1.523(3) . ? C2G H31A 0.9900 . ? C2G H31B 0.9900 . ? C3G C4G 1.512(3) . ? C3G H35A 0.9900 . ? C3G H35B 0.9900 . ? C4G H37A 0.9800 . ? C4G H37B 0.9800 . ? C4G H37C 0.9800 . ? C5G C6G 1.518(3) . ? C5G H21A 0.9900 . ? C5G H21B 0.9900 . ? C6G C7G 1.524(3) . ? C6G H24A 0.9900 . ? C6G H24B 0.9900 . ? C7G C8G 1.518(4) . ? C7G H32A 0.9900 . ? C7G H32B 0.9900 . ? C8G H36A 0.9800 . ? C8G H36B 0.9800 . ? C8G H36C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C10 113.71(15) . . ? C2 C1 H2A 108.8 . . ? C10 C1 H2A 108.8 . . ? C2 C1 H2B 108.8 . . ? C10 C1 H2B 108.8 . . ? H2A C1 H2B 107.7 . . ? C3 C2 C1 110.38(16) . . ? C3 C2 H11A 109.6 . . ? C1 C2 H11A 109.6 . . ? C3 C2 H11B 109.6 . . ? C1 C2 H11B 109.6 . . ? H11A C2 H11B 108.1 . . ? C3 O3 H3B 105.7(4) . . ? O3 C3 C2 112.94(17) . . ? O3 C3 C4 106.84(16) . . ? C2 C3 C4 110.84(15) . . ? O3 C3 H14 108.7 . . ? C2 C3 H14 108.7 . . ? C4 C3 H14 108.7 . . ? C3 C4 C5 113.81(16) . . ? C3 C4 H15A 108.8 . . ? C5 C4 H15A 108.8 . . ? C3 C4 H15B 108.8 . . ? C5 C4 H15B 108.8 . . ? H15A C4 H15B 107.7 . . ? C4 C5 C6 111.31(16) . . ? C4 C5 C10 112.45(15) . . ? C6 C5 C10 111.41(15) . . ? C4 C5 H5 107.1 . . ? C6 C5 H5 107.1 . . ? C10 C5 H5 107.1 . . ? C7 C6 C5 112.92(15) . . ? C7 C6 H17A 109.0 . . ? C5 C6 H17A 109.0 . . ? C7 C6 H17B 109.0 . . ? C5 C6 H17B 109.0 . . ? H17A C6 H17B 107.8 . . ? C8 C7 C6 113.08(16) . . ? C8 C7 H10A 109.0 . . ? C6 C7 H10A 109.0 . . ? C8 C7 H10B 109.0 . . ? C6 C7 H10B 109.0 . . ? H10A C7 H10B 107.8 . . ? C7 C8 C14 110.98(15) . . ? C7 C8 C9 110.84(15) . . ? C14 C8 C9 108.44(14) . . ? C7 C8 H4 108.8 . . ? C14 C8 H4 108.8 . . ? C9 C8 H4 108.8 . . ? C11 C9 C8 111.21(15) . . ? C11 C9 C10 113.75(14) . . ? C8 C9 C10 112.39(14) . . ? C11 C9 H6 106.3 . . ? C8 C9 H6 106.3 . . ? C10 C9 H6 106.3 . . ? C19 C10 C1 107.05(15) . . ? C19 C10 C5 109.65(15) . . ? C1 C10 C5 108.12(14) . . ? C19 C10 C9 111.36(15) . . ? C1 C10 C9 111.73(14) . . ? C5 C10 C9 108.86(14) . . ? C9 C11 C12 113.27(15) . . ? C9 C11 H7A 108.9 . . ? C12 C11 H7A 108.9 . . ? C9 C11 H7B 108.9 . . ? C12 C11 H7B 108.9 . . ? H7A C11 H7B 107.7 . . ? C12 O12 H12 109.5 . . ? O12 C12 C13 111.84(16) . . ? O12 C12 C11 107.21(17) . . ? C13 C12 C11 111.02(15) . . ? O12 C12 H8 108.9 . . ? C13 C12 H8 108.9 . . ? C11 C12 H8 108.9 . . ? C12 C13 C18 108.86(16) . . ? C12 C13 C14 108.80(15) . . ? C18 C13 C14 112.26(15) . . ? C12 C13 C17 117.92(15) . . ? C18 C13 C17 109.39(15) . . ? C14 C13 C17 99.40(14) . . ? C15 C14 C8 118.70(15) . . ? C15 C14 C13 104.46(15) . . ? C8 C14 C13 115.08(15) . . ? C15 C14 H3 105.9 . . ? C8 C14 H3 105.9 . . ? C13 C14 H3 105.9 . . ? C14 C15 C16 103.58(16) . . ? C14 C15 H20A 111.0 . . ? C16 C15 H20A 111.0 . . ? C14 C15 H20B 111.0 . . ? C16 C15 H20B 111.0 . . ? H20A C15 H20B 109.0 . . ? C15 C16 C17 106.85(16) . . ? C15 C16 H33A 110.4 . . ? C17 C16 H33A 110.4 . . ? C15 C16 H33B 110.4 . . ? C17 C16 H33B 110.4 . . ? H33A C16 H33B 108.6 . . ? C20 C17 C16 113.65(16) . . ? C20 C17 C13 119.61(16) . . ? C16 C17 C13 102.96(15) . . ? C20 C17 H28 106.6 . . ? C16 C17 H28 106.6 . . ? C13 C17 H28 106.6 . . ? C13 C18 H19A 109.5 . . ? C13 C18 H19B 109.5 . . ? H19A C18 H19B 109.5 . . ? C13 C18 H19C 109.5 . . ? H19A C18 H19C 109.5 . . ? H19B C18 H19C 109.5 . . ? C10 C19 H23A 109.5 . . ? C10 C19 H23B 109.5 . . ? H23A C19 H23B 109.5 . . ? C10 C19 H23C 109.5 . . ? H23A C19 H23C 109.5 . . ? H23B C19 H23C 109.5 . . ? C21 C20 C22 109.53(16) . . ? C21 C20 C17 112.20(16) . . ? C22 C20 C17 109.60(16) . . ? C21 C20 H26 108.5 . . ? C22 C20 H26 108.5 . . ? C17 C20 H26 108.5 . . ? C20 C21 H34A 109.5 . . ? C20 C21 H34B 109.5 . . ? H34A C21 H34B 109.5 . . ? C20 C21 H34C 109.5 . . ? H34A C21 H34C 109.5 . . ? H34B C21 H34C 109.5 . . ? C23 C22 C20 115.79(16) . . ? C23 C22 H29A 108.3 . . ? C20 C22 H29A 108.3 . . ? C23 C22 H29B 108.3 . . ? C20 C22 H29B 108.3 . . ? H29A C22 H29B 107.4 . . ? C24 C23 C22 112.75(16) . . ? C24 C23 H25A 109.0 . . ? C22 C23 H25A 109.0 . . ? C24 C23 H25B 109.0 . . ? C22 C23 H25B 109.0 . . ? H25A C23 H25B 107.8 . . ? O24B C24 O24A 124.6(2) . . ? O24B C24 C23 118.58(19) . . ? O24A C24 C23 116.82(18) . . ? C1G N1G C5G 114.40(16) . . ? C1G N1G H1 106.9 . . ? C5G N1G H1 106.3 . . ? C1G N1G H2 109.4 . . ? C5G N1G H2 107.3 . . ? H1 N1G H2 112.7 . . ? N1G C1G C2G 111.07(17) . . ? N1G C1G H27A 109.4 . . ? C2G C1G H27A 109.4 . . ? N1G C1G H27B 109.4 . . ? C2G C1G H27B 109.4 . . ? H27A C1G H27B 108.0 . . ? C1G C2G C3G 111.99(19) . . ? C1G C2G H31A 109.2 . . ? C3G C2G H31A 109.2 . . ? C1G C2G H31B 109.2 . . ? C3G C2G H31B 109.2 . . ? H31A C2G H31B 107.9 . . ? C4G C3G C2G 114.3(2) . . ? C4G C3G H35A 108.7 . . ? C2G C3G H35A 108.7 . . ? C4G C3G H35B 108.7 . . ? C2G C3G H35B 108.7 . . ? H35A C3G H35B 107.6 . . ? C3G C4G H37A 109.5 . . ? C3G C4G H37B 109.5 . . ? H37A C4G H37B 109.5 . . ? C3G C4G H37C 109.5 . . ? H37A C4G H37C 109.5 . . ? H37B C4G H37C 109.5 . . ? N1G C5G C6G 110.36(17) . . ? N1G C5G H21A 109.6 . . ? C6G C5G H21A 109.6 . . ? N1G C5G H21B 109.6 . . ? C6G C5G H21B 109.6 . . ? H21A C5G H21B 108.1 . . ? C5G C6G C7G 112.09(19) . . ? C5G C6G H24A 109.2 . . ? C7G C6G H24A 109.2 . . ? C5G C6G H24B 109.2 . . ? C7G C6G H24B 109.2 . . ? H24A C6G H24B 107.9 . . ? C8G C7G C6G 113.3(2) . . ? C8G C7G H32A 108.9 . . ? C6G C7G H32A 108.9 . . ? C8G C7G H32B 108.9 . . ? C6G C7G H32B 108.9 . . ? H32A C7G H32B 107.7 . . ? C7G C8G H36A 109.5 . . ? C7G C8G H36B 109.5 . . ? H36A C8G H36B 109.5 . . ? C7G C8G H36C 109.5 . . ? H36A C8G H36C 109.5 . . ? H36B C8G H36C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C1 C2 C3 58.7(2) . . . . ? C1 C2 C3 O3 -174.54(15) . . . . ? C1 C2 C3 C4 -54.70(19) . . . . ? O3 C3 C4 C5 176.46(16) . . . . ? C2 C3 C4 C5 53.0(2) . . . . ? C3 C4 C5 C6 -178.31(15) . . . . ? C3 C4 C5 C10 -52.5(2) . . . . ? C4 C5 C6 C7 72.3(2) . . . . ? C10 C5 C6 C7 -54.1(2) . . . . ? C5 C6 C7 C8 51.7(2) . . . . ? C6 C7 C8 C14 -172.09(16) . . . . ? C6 C7 C8 C9 -51.5(2) . . . . ? C7 C8 C9 C11 -175.89(17) . . . . ? C14 C8 C9 C11 -53.83(19) . . . . ? C7 C8 C9 C10 55.27(19) . . . . ? C14 C8 C9 C10 177.33(15) . . . . ? C2 C1 C10 C19 -174.16(16) . . . . ? C2 C1 C10 C5 -56.10(19) . . . . ? C2 C1 C10 C9 63.7(2) . . . . ? C4 C5 C10 C19 168.10(15) . . . . ? C6 C5 C10 C19 -66.13(19) . . . . ? C4 C5 C10 C1 51.72(18) . . . . ? C6 C5 C10 C1 177.48(16) . . . . ? C4 C5 C10 C9 -69.84(19) . . . . ? C6 C5 C10 C9 55.92(18) . . . . ? C11 C9 C10 C19 -63.9(2) . . . . ? C8 C9 C10 C19 63.6(2) . . . . ? C11 C9 C10 C1 55.7(2) . . . . ? C8 C9 C10 C1 -176.76(15) . . . . ? C11 C9 C10 C5 175.08(16) . . . . ? C8 C9 C10 C5 -57.42(18) . . . . ? C8 C9 C11 C12 55.6(2) . . . . ? C10 C9 C11 C12 -176.31(15) . . . . ? C9 C11 C12 O12 67.0(2) . . . . ? C9 C11 C12 C13 -55.4(2) . . . . ? O12 C12 C13 C18 171.02(15) . . . . ? C11 C12 C13 C18 -69.3(2) . . . . ? O12 C12 C13 C14 -66.36(18) . . . . ? C11 C12 C13 C14 53.3(2) . . . . ? O12 C12 C13 C17 45.7(2) . . . . ? C11 C12 C13 C17 165.40(17) . . . . ? C7 C8 C14 C15 -56.7(2) . . . . ? C9 C8 C14 C15 -178.68(16) . . . . ? C7 C8 C14 C13 178.51(16) . . . . ? C9 C8 C14 C13 56.5(2) . . . . ? C12 C13 C14 C15 171.38(17) . . . . ? C18 C13 C14 C15 -68.07(18) . . . . ? C17 C13 C14 C15 47.48(17) . . . . ? C12 C13 C14 C8 -56.7(2) . . . . ? C18 C13 C14 C8 63.9(2) . . . . ? C17 C13 C14 C8 179.41(15) . . . . ? C8 C14 C15 C16 -163.74(17) . . . . ? C13 C14 C15 C16 -33.94(19) . . . . ? C14 C15 C16 C17 6.8(2) . . . . ? C15 C16 C17 C20 153.08(17) . . . . ? C15 C16 C17 C13 22.2(2) . . . . ? C12 C13 C17 C20 73.8(2) . . . . ? C18 C13 C17 C20 -51.2(2) . . . . ? C14 C13 C17 C20 -168.96(16) . . . . ? C12 C13 C17 C16 -159.00(17) . . . . ? C18 C13 C17 C16 75.9(2) . . . . ? C14 C13 C17 C16 -41.79(19) . . . . ? C16 C17 C20 C21 179.38(18) . . . . ? C13 C17 C20 C21 -58.6(2) . . . . ? C16 C17 C20 C22 57.5(2) . . . . ? C13 C17 C20 C22 179.50(16) . . . . ? C21 C20 C22 C23 69.2(2) . . . . ? C17 C20 C22 C23 -167.26(15) . . . . ? C20 C22 C23 C24 78.7(2) . . . . ? C22 C23 C24 O24B -117.2(2) . . . . ? C22 C23 C24 O24A 64.1(2) . . . . ? C5G N1G C1G C2G 172.69(17) . . . . ? N1G C1G C2G C3G 179.45(17) . . . . ? C1G C2G C3G C4G 178.5(2) . . . . ? C1G N1G C5G C6G -179.17(16) . . . . ? N1G C5G C6G C7G 176.63(16) . . . . ? C5G C6G C7G C8G 179.80(18) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.235 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.041 _chemical_name_common 'di-n-butylammonium deoxycholate' data_4 _database_code_depnum_ccdc_archive 'CCDC 886461' #TrackingRef 'REVISED_CIF_DATA_OCT_2012.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (R)-2-butylammonium deoxycholate ; _chemical_formula_moiety ? _chemical_formula_sum 'C28 H51 N O4' _chemical_formula_weight 465.70 _chemical_absolute_configuration rm loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 23.511(4) _cell_length_b 7.6318(12) _cell_length_c 18.196(3) _cell_angle_alpha 90.00 _cell_angle_beta 123.03(2) _cell_angle_gamma 90.00 _cell_volume 2737.3(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10356 _cell_measurement_theta_min 0.03 _cell_measurement_theta_max 26.39 _exptl_crystal_description rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.130 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9912 _exptl_absorpt_correction_T_max 0.9978 _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Duo Apex II diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_reflns_number 10356 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.0420 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 26.39 _reflns_number_total 3026 _reflns_number_gt 2371 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0648P)^2^+0.8688P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef ? _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3026 _refine_ls_number_parameters 307 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0663 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1222 _refine_ls_wR_factor_gt 0.1115 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.41827(16) 0.6423(5) 0.35964(19) 0.0321(7) Uani 1 1 d . . . H5A H 0.4444 0.6336 0.4244 0.039 Uiso 1 1 calc R . . H5B H 0.4370 0.7417 0.3443 0.039 Uiso 1 1 calc R . . C2 C 0.34446(16) 0.6820(4) 0.3264(2) 0.0317(7) Uani 1 1 d . . . H9A H 0.3418 0.7923 0.3530 0.038 Uiso 1 1 calc R . . H9B H 0.3181 0.6976 0.2619 0.038 Uiso 1 1 calc R . . O3 O 0.24287(11) 0.55575(9) 0.31087(15) 0.0373(5) Uani 1 1 d D . . C3 C 0.31424(16) 0.5329(5) 0.3497(2) 0.0321(7) Uani 1 1 d . . . H21 H 0.3376 0.5268 0.4149 0.039 Uiso 1 1 calc R . . C4 C 0.32231(15) 0.36142(10) 0.3166(2) 0.0307(7) Uani 1 1 d . . . H22A H 0.2927 0.3614 0.2518 0.037 Uiso 1 1 calc R . . H22B H 0.3064 0.2667 0.3383 0.037 Uiso 1 1 calc R . . H4 H 0.2340 0.6543 0.3199 0.051(11) Uiso 1 1 d RD . . C5 C 0.39602(16) 0.3191(5) 0.34393(19) 0.0295(7) Uani 1 1 d . . . H8 H 0.4236 0.3042 0.4091 0.035 Uiso 1 1 calc R . . H5 H 0.2943 0.7142 0.0030 0.098(19) Uiso 1 1 d R . . C6 C 0.39938(17) 0.1453(5) 0.3044(2) 0.0349(7) Uani 1 1 d . . . H20A H 0.3754 0.0540 0.3162 0.042 Uiso 1 1 calc R . . H20B H 0.4474 0.1092 0.3334 0.042 Uiso 1 1 calc R . . C7 C 0.36754(16) 0.1576(5) 0.20525(19) 0.0321(7) Uani 1 1 d . . . H14A H 0.3746 0.0453 0.1840 0.038 Uiso 1 1 calc R . . H14B H 0.3181 0.1763 0.1754 0.038 Uiso 1 1 calc R . . C8 C 0.39799(15) 0.3070(4) 0.18113(19) 0.0253(6) Uani 1 1 d . . . H19 H 0.4469 0.2804 0.2062 0.030 Uiso 1 1 calc R . . C9 C 0.39322(15) 0.4825(4) 0.22044(18) 0.0249(6) Uani 1 1 d . . . H3 H 0.3439 0.5033 0.1953 0.030 Uiso 1 1 calc R . . C10 C 0.42863(15) 0.4722(5) 0.32251(18) 0.0285(6) Uani 1 1 d . . . C11 C 0.41796(16) 0.6374(5) 0.19125(19) 0.0308(7) Uani 1 1 d . . . H4A H 0.4674 0.6255 0.2181 0.037 Uiso 1 1 calc R . . H4B H 0.4102 0.7474 0.2134 0.037 Uiso 1 1 calc R . . O12 O 0.31254(11) 0.6955(4) 0.05594(15) 0.0403(6) Uani 1 1 d . . . C12 C 0.38242(15) 0.6510(4) 0.09119(19) 0.0278(6) Uani 1 1 d . . . H10 H 0.4039 0.7477 0.0774 0.033 Uiso 1 1 calc R . . C13 C 0.38900(14) 0.4785(5) 0.05215(18) 0.0252(6) Uani 1 1 d . . . C14 C 0.36193(15) 0.3276(4) 0.08201(18) 0.0253(6) Uani 1 1 d . . . H11 H 0.3137 0.3572 0.0596 0.030 Uiso 1 1 calc R . . C15 C 0.35967(17) 0.1704(5) 0.0283(2) 0.0333(7) Uani 1 1 d . . . H23A H 0.3243 0.0859 0.0187 0.040 Uiso 1 1 calc R . . H23B H 0.4040 0.1096 0.0583 0.040 Uiso 1 1 calc R . . C16 C 0.34257(17) 0.2510(5) -0.0598(2) 0.0344(7) Uani 1 1 d . . . H26A H 0.2972 0.2116 -0.1083 0.041 Uiso 1 1 calc R . . H26B H 0.3766 0.2144 -0.0728 0.041 Uiso 1 1 calc R . . C17 C 0.34356(15) 0.4540(4) -0.04961(18) 0.0262(6) Uani 1 1 d . . . H18 H 0.2965 0.4916 -0.0695 0.031 Uiso 1 1 calc R . . C18 C 0.46403(14) 0.4538(5) 0.08373(19) 0.0314(7) Uani 1 1 d . . . H17A H 0.4804 0.5591 0.0699 0.047 Uiso 1 1 calc R . . H17B H 0.4684 0.3524 0.0541 0.047 Uiso 1 1 calc R . . H17C H 0.4911 0.4344 0.1472 0.047 Uiso 1 1 calc R . . C19 C 0.50535(16) 0.4425(5) 0.3686(2) 0.0400(8) Uani 1 1 d . . . H24A H 0.5264 0.5471 0.3621 0.060 Uiso 1 1 calc R . . H24B H 0.5135 0.3417 0.3421 0.060 Uiso 1 1 calc R . . H24C H 0.5251 0.4196 0.4310 0.060 Uiso 1 1 calc R . . C20 C 0.36353(16) 0.5514(5) -0.10682(19) 0.0309(7) Uani 1 1 d . . . H25 H 0.4111 0.5171 -0.0859 0.037 Uiso 1 1 calc R . . C21 C 0.3621(2) 0.7515(5) -0.0976(2) 0.0491(10) Uani 1 1 d . . . H29A H 0.3682 0.8088 -0.1410 0.074 Uiso 1 1 calc R . . H29B H 0.3987 0.7867 -0.0385 0.074 Uiso 1 1 calc R . . H29C H 0.3183 0.7863 -0.1073 0.074 Uiso 1 1 calc R . . C22 C 0.31756(15) 0.4950(5) -0.20314(18) 0.0316(7) Uani 1 1 d . . . H27A H 0.3197 0.3659 -0.2065 0.038 Uiso 1 1 calc R . . H27B H 0.2701 0.5266 -0.2245 0.038 Uiso 1 1 calc R . . C23 C 0.33633(16) 0.5778(5) -0.26397(19) 0.0350(7) Uani 1 1 d . . . H28A H 0.3254 0.7043 -0.2696 0.042 Uiso 1 1 calc R . . H28B H 0.3860 0.5674 -0.2358 0.042 Uiso 1 1 calc R . . C24 C 0.30147(16) 0.4997(5) -0.35565(19) 0.0332(7) Uani 1 1 d . . . O24A O 0.29682(15) 0.5955(4) -0.41517(15) 0.0556(8) Uani 1 1 d . . . O24B O 0.28024(14) 0.3469(4) -0.36960(15) 0.0490(6) Uani 1 1 d . . . N1G N 0.30267(13) 0.9543(4) -0.42363(17) 0.0342(6) Uani 1 1 d . . . H1G1 H 0.3034 0.8352 -0.4212 0.051 Uiso 1 1 calc R . . H1G2 H 0.2700 0.9899 -0.4787 0.051 Uiso 1 1 calc R . . H1G3 H 0.2936 0.9979 -0.3845 0.051 Uiso 1 1 calc R . . C1G C 0.3710(2) 1.0208(6) -0.4011(3) 0.0572(11) Uani 1 1 d . . . H30 H 0.3700 1.1518 -0.4006 0.069 Uiso 1 1 calc R . . C2G C 0.4262(2) 0.9600(7) -0.3117(3) 0.0671(13) Uani 1 1 d . . . H31A H 0.4230 0.8312 -0.3087 0.081 Uiso 1 1 calc R . . H31B H 0.4706 0.9869 -0.3032 0.081 Uiso 1 1 calc R . . C3G C 0.4242(2) 1.0405(8) -0.2385(3) 0.0747(14) Uani 1 1 d . . . H32A H 0.4269 1.1683 -0.2410 0.112 Uiso 1 1 calc R . . H32B H 0.4626 0.9978 -0.1823 0.112 Uiso 1 1 calc R . . H32C H 0.3817 1.0084 -0.2440 0.112 Uiso 1 1 calc R . . C4G C 0.3841(2) 0.9641(9) -0.4711(3) 0.0773(14) Uani 1 1 d . . . H33A H 0.3833 0.8359 -0.4746 0.116 Uiso 1 1 calc R . . H33B H 0.4285 1.0073 -0.4556 0.116 Uiso 1 1 calc R . . H33C H 0.3487 1.0125 -0.5279 0.116 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0430(18) 0.0269(15) 0.0256(15) -0.0021(13) 0.0182(14) -0.0060(14) C2 0.0448(18) 0.0209(14) 0.0324(16) -0.0001(13) 0.0230(14) 0.0017(14) O3 0.0424(13) 0.0304(12) 0.0474(13) -0.0001(10) 0.0300(11) 0.0035(10) C3 0.0405(18) 0.0308(16) 0.0294(15) 0.0005(13) 0.0219(14) 0.0005(14) C4 0.0400(18) 0.0252(15) 0.0312(16) 0.0015(13) 0.0221(14) -0.0032(14) C5 0.0377(18) 0.0249(15) 0.0258(15) 0.0048(13) 0.0172(14) 0.0025(13) C6 0.0460(19) 0.0255(16) 0.0385(17) 0.0068(14) 0.0264(15) 0.0063(15) C7 0.0480(19) 0.0184(14) 0.0354(16) 0.0011(13) 0.0264(15) 0.0007(14) C8 0.0280(15) 0.0175(14) 0.0299(15) 0.0009(11) 0.0154(13) 0.0028(11) C9 0.0265(15) 0.0204(13) 0.0286(14) 0.0024(12) 0.0155(12) 0.0008(12) C10 0.0317(16) 0.0259(15) 0.0250(15) 0.0010(13) 0.0136(13) 0.0015(14) C11 0.0378(17) 0.0217(14) 0.0336(16) -0.0022(13) 0.0198(14) -0.0046(13) O12 0.0404(13) 0.0383(13) 0.0400(14) 0.0083(10) 0.0205(11) 0.0144(11) C12 0.0316(16) 0.0209(14) 0.0328(16) 0.0033(13) 0.0188(13) -0.0018(13) C13 0.0239(14) 0.0233(14) 0.0270(15) 0.0006(13) 0.0130(12) -0.0001(13) C14 0.0272(15) 0.0216(14) 0.0262(15) -0.0011(12) 0.0139(12) -0.0016(12) C15 0.0417(18) 0.0247(15) 0.0368(17) -0.0019(14) 0.0234(14) -0.0025(14) C16 0.0445(19) 0.0266(16) 0.0328(17) -0.0032(14) 0.0216(15) -0.0042(14) C17 0.0266(15) 0.0270(15) 0.0235(15) 0.0005(12) 0.0128(13) -0.0009(13) C18 0.0252(15) 0.0366(18) 0.0293(16) 0.0002(14) 0.0129(13) -0.0004(14) C19 0.0361(18) 0.045(2) 0.0321(18) 0.0056(15) 0.0142(15) 0.0019(16) C20 0.0338(17) 0.0334(17) 0.0260(15) 0.0012(13) 0.0166(14) -0.0042(14) C21 0.080(3) 0.0354(18) 0.0330(18) -0.0028(16) 0.0312(19) -0.0158(19) C22 0.0357(17) 0.0288(16) 0.0286(15) 0.0002(13) 0.0164(13) -0.0007(14) C23 0.0389(18) 0.0359(17) 0.0311(16) 0.0015(14) 0.0196(14) -0.0054(15) C24 0.0438(19) 0.0290(16) 0.0302(16) 0.0018(14) 0.0223(15) -0.0017(15) O24A 0.099(2) 0.0341(13) 0.0357(13) -0.0024(11) 0.0380(14) -0.0161(13) O24B 0.0755(18) 0.0359(14) 0.0401(14) -0.0027(12) 0.0345(13) -0.0142(13) N1G 0.0430(16) 0.0299(14) 0.0348(14) -0.0010(12) 0.0244(13) -0.0022(12) C1G 0.054(2) 0.048(2) 0.083(3) 0.018(2) 0.046(2) 0.003(2) C2G 0.041(2) 0.075(3) 0.080(3) 0.024(3) 0.029(2) -0.003(2) C3G 0.060(3) 0.082(4) 0.076(3) 0.000(3) 0.033(2) -0.017(3) C4G 0.073(3) 0.099(4) 0.066(3) -0.006(3) 0.041(3) -0.005(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.524(4) . ? C1 C10 1.543(4) . ? C2 C3 1.520(4) . ? O3 C3 1.433(4) . ? C3 C4 1.496(4) . ? C4 C5 1.554(4) . ? C5 C6 1.531(4) . ? C5 C10 1.559(4) . ? C6 C7 1.534(4) . ? C7 C8 1.532(4) . ? C8 C14 1.526(4) . ? C8 C9 1.551(4) . ? C9 C11 1.534(4) . ? C9 C10 1.570(4) . ? C10 C19 1.536(4) . ? C11 C12 1.538(4) . ? O12 C12 1.441(4) . ? C12 C13 1.543(4) . ? C13 C18 1.540(4) . ? C13 C14 1.551(4) . ? C13 C17 1.565(4) . ? C14 C15 1.529(4) . ? C15 C16 1.553(4) . ? C16 C17 1.559(4) . ? C17 C20 1.546(4) . ? C20 C22 1.536(4) . ? C20 C21 1.538(5) . ? C22 C23 1.534(4) . ? C23 C24 1.523(4) . ? C24 O24B 1.239(4) . ? C24 O24A 1.261(4) . ? N1G C1G 1.513(4) . ? C1G C2G 1.499(6) . ? C1G C4G 1.525(6) . ? C2G C3G 1.491(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C10 114.2(2) . . ? C3 C2 C1 110.2(3) . . ? O3 C3 C4 106.2(2) . . ? O3 C3 C2 111.8(3) . . ? C4 C3 C2 111.1(2) . . ? C3 C4 C5 114.6(2) . . ? C6 C5 C4 111.3(2) . . ? C6 C5 C10 111.9(2) . . ? C4 C5 C10 112.3(2) . . ? C5 C6 C7 112.5(2) . . ? C8 C7 C6 112.2(2) . . ? C14 C8 C7 111.7(2) . . ? C14 C8 C9 108.8(2) . . ? C7 C8 C9 110.4(2) . . ? C11 C9 C8 111.7(2) . . ? C11 C9 C10 113.1(2) . . ? C8 C9 C10 112.2(2) . . ? C19 C10 C1 107.7(2) . . ? C19 C10 C5 110.1(3) . . ? C1 C10 C5 107.7(2) . . ? C19 C10 C9 111.2(2) . . ? C1 C10 C9 111.6(2) . . ? C5 C10 C9 108.5(2) . . ? C9 C11 C12 113.4(2) . . ? O12 C12 C11 107.1(2) . . ? O12 C12 C13 111.8(2) . . ? C11 C12 C13 111.2(2) . . ? C18 C13 C12 108.3(2) . . ? C18 C13 C14 112.6(2) . . ? C12 C13 C14 108.0(2) . . ? C18 C13 C17 109.4(2) . . ? C12 C13 C17 118.1(2) . . ? C14 C13 C17 100.4(2) . . ? C8 C14 C15 118.5(2) . . ? C8 C14 C13 114.9(2) . . ? C15 C14 C13 103.7(2) . . ? C14 C15 C16 104.4(2) . . ? C15 C16 C17 107.0(2) . . ? C20 C17 C16 112.8(2) . . ? C20 C17 C13 118.5(2) . . ? C16 C17 C13 102.5(2) . . ? C22 C20 C21 111.0(3) . . ? C22 C20 C17 110.5(2) . . ? C21 C20 C17 111.7(3) . . ? C23 C22 C20 114.1(3) . . ? C24 C23 C22 115.7(3) . . ? O24B C24 O24A 122.2(3) . . ? O24B C24 C23 120.6(3) . . ? O24A C24 C23 117.2(3) . . ? C2G C1G N1G 110.7(3) . . ? C2G C1G C4G 111.7(4) . . ? N1G C1G C4G 110.2(4) . . ? C3G C2G C1G 114.3(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.364 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.039 _chemical_name_common '(R)-2-butylammonium deoxycholate' data_5 _database_code_depnum_ccdc_archive 'CCDC 886462' #TrackingRef 'REVISED_CIF_DATA_OCT_2012.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (S)-2-butylammonium deoxycholate ; _chemical_formula_moiety ? _chemical_formula_sum 'C28 H51 N O4' _chemical_formula_weight 465.70 _chemical_absolute_configuration rm loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.1547(11) _cell_length_b 7.5678(8) _cell_length_c 17.645(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.915(3) _cell_angle_gamma 90.00 _cell_volume 1355.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 12140 _cell_measurement_theta_min 0.17 _cell_measurement_theta_max 28.32 _exptl_crystal_description rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.141 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type none _exptl_special_details ; none ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Duo Apex II diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_reflns_number 12140 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0345 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 28.32 _reflns_number_total 3604 _reflns_number_gt 3138 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0592P)^2^+0.1308P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3604 _refine_ls_number_parameters 308 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1046 _refine_ls_wR_factor_gt 0.0986 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.33024(19) 0.6986(3) 0.76114(12) 0.0293(4) Uani 1 1 d . . . H1A H 0.3829 0.6884 0.8087 0.035 Uiso 1 1 calc R . . H1B H 0.3664 0.7983 0.7317 0.035 Uiso 1 1 calc R . . N1G N -0.12462(17) 0.4897(3) 0.97513(10) 0.0323(4) Uani 1 1 d . . . C1G C -0.2424(2) 0.6052(4) 0.98293(12) 0.0389(5) Uani 1 1 d . . . H29 H -0.2124 0.7292 0.9924 0.047 Uiso 1 1 calc R . . C2 C 0.1880(2) 0.7400(3) 0.78086(12) 0.0301(4) Uani 1 1 d . . . H2A H 0.1844 0.8519 0.8098 0.036 Uiso 1 1 calc R . . H3A H 0.1349 0.7549 0.7338 0.036 Uiso 1 1 calc R . . C2G C -0.3214(3) 0.5998(5) 0.90876(14) 0.0557(7) Uani 1 1 d . . . H30A H -0.2643 0.6327 0.8668 0.084 Uiso 1 1 calc R . . H30B H -0.3950 0.6831 0.9114 0.084 Uiso 1 1 calc R . . H30C H -0.3555 0.4801 0.9004 0.084 Uiso 1 1 calc R . . O3 O -0.00487(15) 0.6211(2) 0.84333(9) 0.0386(4) Uani 1 1 d . . . C3 C 0.1316(2) 0.5906(3) 0.82786(12) 0.0295(4) Uani 1 1 d . . . H3B H 0.1819 0.5826 0.8769 0.035 Uiso 1 1 calc R . . C3G C -0.3202(3) 0.5421(5) 1.05097(14) 0.0564(8) Uani 1 1 d . . . H32A H -0.3415 0.4154 1.0440 0.068 Uiso 1 1 calc R . . H32B H -0.2637 0.5526 1.0970 0.068 Uiso 1 1 calc R . . C4 C 0.1422(2) 0.4157(3) 0.78646(11) 0.0286(4) Uani 1 1 d . . . H5A H 0.0829 0.4180 0.7414 0.034 Uiso 1 1 calc R . . H4A H 0.1119 0.3198 0.8202 0.034 Uiso 1 1 calc R . . C4G C -0.4467(3) 0.6423(7) 1.06371(19) 0.0901(15) Uani 1 1 d . . . H33A H -0.4281 0.7693 1.0655 0.135 Uiso 1 1 calc R . . H33B H -0.4849 0.6050 1.1118 0.135 Uiso 1 1 calc R . . H33C H -0.5090 0.6175 1.0221 0.135 Uiso 1 1 calc R . . H52 H -0.0133 0.7423 0.8567 0.079(11) Uiso 1 1 d R . . H54 H -0.0740 0.4897 1.0182 0.042(7) Uiso 1 1 d R . . H56 H -0.0774 0.5188 0.9385 0.032(6) Uiso 1 1 d R . . H55 H -0.1435 0.3716 0.9685 0.064(9) Uiso 1 1 d R . . H53 H 0.0737 0.7720 0.4815 0.077(11) Uiso 1 1 d R . . C5 C 0.2835(2) 0.3741(3) 0.76089(12) 0.0280(4) Uani 1 1 d . . . H5 H 0.3387 0.3584 0.8079 0.034 Uiso 1 1 calc R . . C6 C 0.2879(2) 0.1987(3) 0.71713(12) 0.0335(5) Uani 1 1 d . . . H6B H 0.3808 0.1608 0.7126 0.040 Uiso 1 1 calc R . . H6A H 0.2410 0.1071 0.7463 0.040 Uiso 1 1 calc R . . C7 C 0.2256(2) 0.2116(2) 0.63766(12) 0.0289(4) Uani 1 1 d . . . H7A H 0.2391 0.0987 0.6105 0.035 Uiso 1 1 calc R . . H7B H 0.1295 0.2305 0.6422 0.035 Uiso 1 1 calc R . . C8 C 0.28446(18) 0.3628(2) 0.59145(11) 0.0218(4) Uani 1 1 d . . . H8 H 0.3793 0.3358 0.5825 0.026 Uiso 1 1 calc R . . C9 C 0.27604(17) 0.5380(2) 0.63578(10) 0.0198(3) Uani 1 1 d . . . H9 H 0.1805 0.5591 0.6453 0.024 Uiso 1 1 calc R . . C10 C 0.34573(18) 0.5273(3) 0.71510(11) 0.0247(4) Uani 1 1 d . . . C11 C 0.32371(19) 0.6943(3) 0.58799(11) 0.0254(4) Uani 1 1 d . . . H11A H 0.3096 0.8050 0.6166 0.030 Uiso 1 1 calc R . . H12A H 0.4196 0.6817 0.5801 0.030 Uiso 1 1 calc R . . O12 O 0.11970(14) 0.7564(2) 0.52489(9) 0.0336(3) Uani 1 1 d . . . C12 C 0.25422(18) 0.7098(2) 0.51062(11) 0.0233(4) Uani 1 1 d . . . H12 H 0.2961 0.8074 0.4814 0.028 Uiso 1 1 calc R . . C13 C 0.26599(16) 0.5369(2) 0.46537(10) 0.0196(3) Uani 1 1 d . . . C14 C 0.21442(17) 0.3843(2) 0.51473(11) 0.0202(4) Uani 1 1 d . . . H14 H 0.1204 0.4125 0.5257 0.024 Uiso 1 1 calc R . . C15 C 0.2121(2) 0.2256(3) 0.46041(12) 0.0275(4) Uani 1 1 d . . . H15A H 0.1442 0.1388 0.4752 0.033 Uiso 1 1 calc R . . H15B H 0.2989 0.1661 0.4597 0.033 Uiso 1 1 calc R . . C16 C 0.1782(2) 0.3083(3) 0.38213(12) 0.0284(4) Uani 1 1 d . . . H16A H 0.0909 0.2668 0.3639 0.034 Uiso 1 1 calc R . . H16B H 0.2450 0.2740 0.3446 0.034 Uiso 1 1 calc R . . C17 C 0.17730(17) 0.5125(2) 0.39291(11) 0.0221(4) Uani 1 1 d . . . H17 H 0.0857 0.5470 0.4067 0.026 Uiso 1 1 calc R . . C18 C 0.41143(17) 0.5127(3) 0.44389(11) 0.0267(4) Uani 1 1 d . . . H18B H 0.4441 0.6219 0.4209 0.040 Uiso 1 1 calc R . . H18C H 0.4188 0.4154 0.4076 0.040 Uiso 1 1 calc R . . H18A H 0.4639 0.4855 0.4895 0.040 Uiso 1 1 calc R . . C19 C 0.49475(19) 0.4942(3) 0.70755(13) 0.0361(5) Uani 1 1 d . . . H19B H 0.5358 0.5967 0.6835 0.054 Uiso 1 1 calc R . . H19C H 0.5089 0.3890 0.6764 0.054 Uiso 1 1 calc R . . H19A H 0.5343 0.4759 0.7580 0.054 Uiso 1 1 calc R . . C20 C 0.21272(18) 0.6172(3) 0.32107(11) 0.0249(4) Uani 1 1 d . . . H20 H 0.3085 0.5982 0.3115 0.030 Uiso 1 1 calc R . . C21 C 0.1910(2) 0.8162(3) 0.33223(12) 0.0310(4) Uani 1 1 d . . . H21A H 0.1004 0.8372 0.3484 0.047 Uiso 1 1 calc R . . H21C H 0.2061 0.8781 0.2843 0.047 Uiso 1 1 calc R . . H21B H 0.2526 0.8605 0.3711 0.047 Uiso 1 1 calc R . . C22 C 0.13460(19) 0.5518(3) 0.25056(11) 0.0281(4) Uani 1 1 d . . . H22A H 0.1398 0.4213 0.2481 0.034 Uiso 1 1 calc R . . H22B H 0.0408 0.5846 0.2558 0.034 Uiso 1 1 calc R . . C23 C 0.1861(2) 0.6292(4) 0.17693(12) 0.0446(6) Uani 1 1 d . . . H23A H 0.1784 0.7594 0.1798 0.054 Uiso 1 1 calc R . . H23B H 0.2811 0.6008 0.1739 0.054 Uiso 1 1 calc R . . C24 C 0.1194(2) 0.5683(3) 0.10394(12) 0.0315(4) Uani 1 1 d . . . O24A O 0.15893(17) 0.6342(2) 0.04344(9) 0.0437(4) Uani 1 1 d . . . O24B O 0.02727(16) 0.4582(2) 0.10734(9) 0.0442(4) Uani 1 1 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 C1 0.0346(10) 0.0266(10) 0.0267(10) -0.0020(8) -0.0020(8) -0.0069(8) N1G 0.0330(9) 0.0390(11) 0.0246(9) -0.0024(8) -0.0008(7) -0.0001(8) C1G 0.0376(11) 0.0451(13) 0.0340(11) -0.0054(11) -0.0040(9) 0.0100(10) C2 0.0409(11) 0.0211(9) 0.0284(10) -0.0031(8) 0.0038(8) -0.0016(8) C2G 0.0498(14) 0.081(2) 0.0366(13) 0.0013(14) -0.0076(11) 0.0172(15) O3 0.0416(8) 0.0374(9) 0.0370(8) -0.0006(7) 0.0119(7) 0.0013(7) C3 0.0359(10) 0.0259(10) 0.0268(10) 0.0003(8) 0.0037(8) -0.0012(8) C3G 0.0487(14) 0.086(2) 0.0342(13) -0.0046(14) 0.0038(11) 0.0126(15) C4 0.0361(10) 0.0227(9) 0.0270(10) 0.0023(8) 0.0031(8) -0.0044(8) C4G 0.0567(17) 0.148(4) 0.066(2) -0.037(3) 0.0071(15) 0.020(2) C5 0.0354(10) 0.0230(9) 0.0253(10) 0.0048(8) -0.0053(8) 0.0012(8) C6 0.0460(12) 0.0190(9) 0.0356(12) 0.0064(9) 0.0010(9) 0.0065(9) C7 0.0417(11) 0.0134(8) 0.0316(10) 0.0019(8) 0.0030(8) -0.0005(8) C8 0.0224(8) 0.0148(8) 0.0283(10) 0.0017(7) 0.0016(7) 0.0029(6) C9 0.0194(8) 0.0145(8) 0.0255(9) 0.0001(7) 0.0003(7) -0.0005(6) C10 0.0239(9) 0.0228(9) 0.0273(9) 0.0018(8) -0.0038(7) -0.0005(7) C11 0.0307(9) 0.0175(8) 0.0279(10) 0.0004(7) -0.0031(8) -0.0033(7) O12 0.0338(7) 0.0292(8) 0.0378(8) -0.0014(6) 0.0007(6) 0.0148(6) C12 0.0251(9) 0.0157(8) 0.0290(10) 0.0007(7) 0.0005(7) -0.0006(7) C13 0.0168(8) 0.0172(8) 0.0249(9) 0.0001(7) -0.0012(6) 0.0016(7) C14 0.0206(8) 0.0149(8) 0.0252(9) 0.0004(7) 0.0003(7) 0.0003(6) C15 0.0347(10) 0.0170(9) 0.0308(10) -0.0016(8) -0.0007(8) -0.0013(8) C16 0.0329(10) 0.0219(9) 0.0302(10) -0.0035(8) -0.0020(8) -0.0027(8) C17 0.0199(8) 0.0197(9) 0.0266(9) 0.0005(7) 0.0000(7) -0.0003(7) C18 0.0204(8) 0.0287(10) 0.0311(10) 0.0024(8) 0.0009(7) 0.0012(7) C19 0.0275(10) 0.0442(13) 0.0365(11) 0.0019(10) -0.0074(8) 0.0025(9) C20 0.0241(8) 0.0245(9) 0.0260(9) 0.0030(8) -0.0012(7) -0.0017(7) C21 0.0370(11) 0.0253(10) 0.0308(11) 0.0052(8) -0.0020(9) -0.0033(8) C22 0.0306(9) 0.0285(10) 0.0252(9) 0.0011(8) -0.0019(8) -0.0041(8) C23 0.0441(12) 0.0611(16) 0.0285(11) 0.0043(12) -0.0014(9) -0.0221(12) C24 0.0382(11) 0.0303(10) 0.0260(10) 0.0014(8) -0.0018(8) 0.0002(8) O24A 0.0625(10) 0.0410(9) 0.0278(8) 0.0031(7) 0.0026(7) -0.0097(8) O24B 0.0536(10) 0.0462(10) 0.0324(8) 0.0089(7) -0.0102(7) -0.0193(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.523(3) . ? C1 C10 1.539(3) . ? N1G C1G 1.490(3) . ? C1G C2G 1.524(3) . ? C1G C3G 1.524(3) . ? C2 C3 1.520(3) . ? O3 C3 1.436(2) . ? C3 C4 1.517(3) . ? C3G C4G 1.511(4) . ? C4 C5 1.544(3) . ? C5 C6 1.537(3) . ? C5 C10 1.553(3) . ? C6 C7 1.532(3) . ? C7 C8 1.532(3) . ? C8 C14 1.528(3) . ? C8 C9 1.543(2) . ? C9 C11 1.535(3) . ? C9 C10 1.560(3) . ? C10 C19 1.542(3) . ? C11 C12 1.531(3) . ? O12 C12 1.437(2) . ? C12 C13 1.538(2) . ? C13 C18 1.542(2) . ? C13 C14 1.543(2) . ? C13 C17 1.563(2) . ? C14 C15 1.536(3) . ? C15 C16 1.550(3) . ? C16 C17 1.557(3) . ? C17 C20 1.542(3) . ? C20 C21 1.535(3) . ? C20 C22 1.546(3) . ? C22 C23 1.525(3) . ? C23 C24 1.518(3) . ? C24 O24A 1.251(3) . ? C24 O24B 1.255(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C10 113.54(16) . . ? N1G C1G C2G 108.46(19) . . ? N1G C1G C3G 108.4(2) . . ? C2G C1G C3G 113.3(2) . . ? C3 C2 C1 109.77(17) . . ? O3 C3 C4 107.91(17) . . ? O3 C3 C2 110.95(17) . . ? C4 C3 C2 110.89(16) . . ? C4G C3G C1G 114.3(3) . . ? C3 C4 C5 113.04(17) . . ? C6 C5 C4 110.92(17) . . ? C6 C5 C10 111.60(16) . . ? C4 C5 C10 112.81(16) . . ? C7 C6 C5 112.94(16) . . ? C8 C7 C6 112.07(16) . . ? C14 C8 C7 111.77(15) . . ? C14 C8 C9 109.21(14) . . ? C7 C8 C9 110.29(15) . . ? C11 C9 C8 111.30(14) . . ? C11 C9 C10 112.97(14) . . ? C8 C9 C10 112.46(14) . . ? C1 C10 C19 106.92(16) . . ? C1 C10 C5 107.95(16) . . ? C19 C10 C5 109.37(16) . . ? C1 C10 C9 112.39(15) . . ? C19 C10 C9 111.27(15) . . ? C5 C10 C9 108.85(15) . . ? C12 C11 C9 113.82(15) . . ? O12 C12 C11 106.77(15) . . ? O12 C12 C13 112.43(15) . . ? C11 C12 C13 111.04(15) . . ? C12 C13 C18 108.14(15) . . ? C12 C13 C14 108.29(14) . . ? C18 C13 C14 112.64(14) . . ? C12 C13 C17 118.46(14) . . ? C18 C13 C17 109.06(14) . . ? C14 C13 C17 100.19(14) . . ? C8 C14 C15 118.17(15) . . ? C8 C14 C13 114.98(14) . . ? C15 C14 C13 103.60(14) . . ? C14 C15 C16 103.97(15) . . ? C15 C16 C17 107.07(16) . . ? C20 C17 C16 114.06(16) . . ? C20 C17 C13 118.21(15) . . ? C16 C17 C13 102.27(15) . . ? C21 C20 C17 111.27(16) . . ? C21 C20 C22 110.13(17) . . ? C17 C20 C22 111.93(15) . . ? C23 C22 C20 112.57(16) . . ? C24 C23 C22 116.83(18) . . ? O24A C24 O24B 123.8(2) . . ? O24A C24 C23 117.25(19) . . ? O24B C24 C23 118.98(19) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.275 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.036 _chemical_name_common '(S)-2-butylammonium deoxycholate' data_6 _database_code_depnum_ccdc_archive 'CCDC 886463' #TrackingRef 'REVISED_CIF_DATA_OCT_2012.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (R)-3-methyl-2-butylammonium deoxycholate ; _chemical_formula_moiety ? _chemical_formula_sum 'C29 H53 N O4' _chemical_formula_weight 479.72 _chemical_absolute_configuration rm loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.501(2) _cell_length_b 7.7042(15) _cell_length_c 17.175(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.19(3) _cell_angle_gamma 90.00 _cell_volume 1461.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8347 _cell_measurement_theta_min 0.38 _cell_measurement_theta_max 25.63 _exptl_crystal_description rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.090 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none _exptl_special_details ; none ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Duo Apex II diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_reflns_number 8347 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0489 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.63 _reflns_number_total 5311 _reflns_number_gt 3472 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0747P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef ? _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 5311 _refine_ls_number_parameters 317 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0869 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1380 _refine_ls_wR_factor_gt 0.1192 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.4610(2) 0.6931(3) 0.68342(17) 0.0545(7) Uani 1 1 d . . . H9A H 1.5435 0.6865 0.7212 0.065 Uiso 1 1 calc R . . H9B H 1.4595 0.7915 0.6461 0.065 Uiso 1 1 calc R . . C2 C 1.3715(3) 0.7290(3) 0.73176(17) 0.0563(7) Uani 1 1 d . . . H14A H 1.3917 0.8404 0.7612 0.068 Uiso 1 1 calc R . . H14B H 1.2887 0.7382 0.6947 0.068 Uiso 1 1 calc R . . O3 O 1.2918(2) 0.6084(3) 0.83773(13) 0.0814(7) Uani 1 1 d . . . H16 H 1.3033 0.7060 0.8604 0.098 Uiso 1 1 calc R . . C3 C 1.3767(3) 0.5835(4) 0.79138(17) 0.0603(7) Uani 1 1 d . . . H20 H 1.4602 0.5781 0.8293 0.072 Uiso 1 1 calc R . . C4 C 1.3487(3) 0.4121(3) 0.74731(17) 0.0596(7) Uani 1 1 d . . . H19A H 1.2635 0.4132 0.7135 0.071 Uiso 1 1 calc R . . H19B H 1.3571 0.3179 0.7877 0.071 Uiso 1 1 calc R . . C5 C 1.4307(2) 0.3726(3) 0.69321(17) 0.0529(7) Uani 1 1 d . . . H10 H 1.5147 0.3591 0.7298 0.064 Uiso 1 1 calc R . . C6 C 1.3970(3) 0.1997(3) 0.64819(19) 0.0643(8) Uani 1 1 d . . . H15A H 1.4630 0.1645 0.6249 0.077 Uiso 1 1 calc R . . H15B H 1.3893 0.1091 0.6874 0.077 Uiso 1 1 calc R . . C7 C 1.2788(3) 0.2103(3) 0.58042(18) 0.0617(7) Uani 1 1 d . . . H8A H 1.2109 0.2307 0.6043 0.074 Uiso 1 1 calc R . . H8B H 1.2642 0.0983 0.5510 0.074 Uiso 1 1 calc R . . C8 C 1.2820(2) 0.3561(3) 0.52066(16) 0.0484(6) Uani 1 1 d . . . H7 H 1.3468 0.3291 0.4940 0.058 Uiso 1 1 calc R . . C9 C 1.3128(2) 0.5305(3) 0.56593(15) 0.0438(6) Uani 1 1 d . . . H2 H 1.2484 0.5514 0.5938 0.053 Uiso 1 1 calc R . . C10 C 1.4347(2) 0.5231(3) 0.63342(16) 0.0488(6) Uani 1 1 d . . . C11 C 1.3058(3) 0.6811(3) 0.50718(16) 0.0536(7) Uani 1 1 d . . . H4A H 1.3736 0.6706 0.4824 0.064 Uiso 1 1 calc R . . H4B H 1.3170 0.7910 0.5382 0.064 Uiso 1 1 calc R . . O12 O 1.0930(2) 0.7373(3) 0.47545(13) 0.0724(6) Uani 1 1 d . . . H12 H 1.0297 0.7622 0.4389 0.087 Uiso 1 1 calc R . . C12 C 1.1870(2) 0.6916(3) 0.43923(16) 0.0523(7) Uani 1 1 d . . . H5 H 1.1942 0.7855 0.4006 0.063 Uiso 1 1 calc R . . C13 C 1.1593(2) 0.5197(3) 0.39262(15) 0.0460(6) Uani 1 1 d . . . C14 C 1.1618(2) 0.3742(3) 0.45472(15) 0.0460(6) Uani 1 1 d . . . H6 H 1.0999 0.4061 0.4831 0.055 Uiso 1 1 calc R . . C15 C 1.1113(3) 0.2156(3) 0.40178(18) 0.0624(8) Uani 1 1 d . . . H13A H 1.1762 0.1540 0.3854 0.075 Uiso 1 1 calc R . . H13B H 1.0720 0.1336 0.4310 0.075 Uiso 1 1 calc R . . C16 C 1.0184(3) 0.2938(4) 0.3278(2) 0.0665(8) Uani 1 1 d . . . H25A H 0.9356 0.2566 0.3268 0.080 Uiso 1 1 calc R . . H25B H 1.0351 0.2540 0.2772 0.080 Uiso 1 1 calc R . . C17 C 1.0290(2) 0.4936(3) 0.33467(16) 0.0506(6) Uani 1 1 d . . . H11 H 0.9710 0.5328 0.3650 0.061 Uiso 1 1 calc R . . C18 C 1.2531(2) 0.4936(4) 0.34514(17) 0.0595(7) Uani 1 1 d . . . H17A H 1.2540 0.5959 0.3114 0.089 Uiso 1 1 calc R . . H17B H 1.2317 0.3908 0.3105 0.089 Uiso 1 1 calc R . . H17C H 1.3335 0.4774 0.3832 0.089 Uiso 1 1 calc R . . C19 C 1.5425(2) 0.4961(4) 0.5978(2) 0.0696(8) Uani 1 1 d . . . H18A H 1.6175 0.4868 0.6421 0.104 Uiso 1 1 calc R . . H18B H 1.5483 0.5951 0.5633 0.104 Uiso 1 1 calc R . . H18C H 1.5303 0.3894 0.5655 0.104 Uiso 1 1 calc R . . C20 C 0.9926(2) 0.5868(4) 0.25190(18) 0.0580(7) Uani 1 1 d . . . H21 H 1.0472 0.5448 0.2197 0.070 Uiso 1 1 calc R . . C21 C 1.0066(3) 0.7855(4) 0.2602(2) 0.0784(9) Uani 1 1 d . . . H28A H 0.9620 0.8282 0.2974 0.118 Uiso 1 1 calc R . . H28B H 0.9741 0.8397 0.2070 0.118 Uiso 1 1 calc R . . H28C H 1.0925 0.8150 0.2817 0.118 Uiso 1 1 calc R . . C22 C 0.8630(2) 0.5386(4) 0.20584(17) 0.0617(7) Uani 1 1 d . . . H22A H 0.8569 0.4105 0.2029 0.074 Uiso 1 1 calc R . . H22B H 0.8084 0.5796 0.2375 0.074 Uiso 1 1 calc R . . C23 C 0.8182(3) 0.6105(5) 0.12081(18) 0.0747(9) Uani 1 1 d . . . H30A H 0.8768 0.5778 0.0907 0.090 Uiso 1 1 calc R . . H30B H 0.8180 0.7387 0.1243 0.090 Uiso 1 1 calc R . . C24 C 0.6935(3) 0.5519(4) 0.07212(19) 0.0652(8) Uani 1 1 d . . . O24A O 0.6358(2) 0.6450(3) 0.01542(17) 0.1056(9) Uani 1 1 d . . . O24B O 0.6501(2) 0.4147(3) 0.08793(14) 0.0960(8) Uani 1 1 d . . . N1G N 0.3909(2) 0.4970(4) 0.00291(14) 0.0698(7) Uani 1 1 d . . . H26A H 0.4733 0.5007 0.0177 0.105 Uiso 1 1 calc R . . H26B H 0.3617 0.5438 -0.0474 0.105 Uiso 1 1 calc R . . H26C H 0.3659 0.3849 0.0023 0.105 Uiso 1 1 calc R . . C1G C 0.3448(3) 0.5985(4) 0.06231(19) 0.0741(9) Uani 1 1 d . . . H29 H 0.3822 0.7160 0.0634 0.089 Uiso 1 1 calc R . . C2G C 0.3948(5) 0.5313(9) 0.1435(2) 0.143(2) Uani 1 1 d . . . H31A H 0.3677 0.4114 0.1460 0.214 Uiso 1 1 calc R . . H31B H 0.3672 0.6028 0.1820 0.214 Uiso 1 1 calc R . . H31C H 0.4834 0.5343 0.1574 0.214 Uiso 1 1 calc R . . C3G C 0.2156(5) 0.6299(11) 0.0358(3) 0.157(3) Uani 1 1 d . . . H36 H 0.1995 0.6729 -0.0212 0.188 Uiso 1 1 calc R . . C4G C 0.1430(7) 0.4878(19) 0.0303(8) 0.421(12) Uani 1 1 d . . . H12A H 0.1310 0.4333 -0.0229 0.631 Uiso 1 1 calc R . . H12B H 0.0645 0.5234 0.0370 0.631 Uiso 1 1 calc R . . H12C H 0.1814 0.4047 0.0729 0.631 Uiso 1 1 calc R . . C5G C 0.1818(7) 0.7851(11) 0.0836(4) 0.212(4) Uani 1 1 d . . . H38A H 0.1766 0.7445 0.1366 0.318 Uiso 1 1 calc R . . H38B H 0.1034 0.8330 0.0530 0.318 Uiso 1 1 calc R . . H38C H 0.2441 0.8752 0.0912 0.318 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0600(16) 0.0408(14) 0.0637(17) 0.0003(13) 0.0187(14) -0.0062(12) C2 0.0693(18) 0.0394(15) 0.0614(17) -0.0028(13) 0.0201(15) 0.0030(12) O3 0.1058(17) 0.0774(15) 0.0753(14) -0.0003(12) 0.0488(14) 0.0077(13) C3 0.0698(18) 0.0560(18) 0.0594(17) 0.0010(14) 0.0251(15) 0.0043(13) C4 0.0717(19) 0.0471(16) 0.0617(17) 0.0103(14) 0.0217(15) -0.0014(13) C5 0.0534(16) 0.0377(13) 0.0658(17) 0.0054(13) 0.0135(13) 0.0056(11) C6 0.080(2) 0.0361(15) 0.074(2) 0.0058(14) 0.0153(17) 0.0099(13) C7 0.0783(19) 0.0316(14) 0.0711(19) 0.0005(13) 0.0142(16) -0.0034(12) C8 0.0560(16) 0.0315(13) 0.0618(16) 0.0015(11) 0.0230(14) 0.0018(10) C9 0.0504(13) 0.0285(12) 0.0579(14) 0.0006(11) 0.0239(12) 0.0017(10) C10 0.0498(14) 0.0357(13) 0.0638(16) -0.0024(12) 0.0205(13) 0.0025(11) C11 0.0731(18) 0.0316(14) 0.0591(16) -0.0007(12) 0.0236(15) -0.0115(12) O12 0.0805(14) 0.0562(12) 0.0860(14) -0.0023(11) 0.0326(12) 0.0248(11) C12 0.0679(17) 0.0348(14) 0.0582(17) 0.0030(12) 0.0239(15) -0.0038(12) C13 0.0502(14) 0.0353(13) 0.0572(15) 0.0001(12) 0.0224(12) 0.0009(11) C14 0.0527(15) 0.0279(12) 0.0611(16) 0.0002(12) 0.0221(13) -0.0016(10) C15 0.0682(18) 0.0355(15) 0.081(2) -0.0062(14) 0.0173(17) -0.0052(12) C16 0.0663(18) 0.0482(16) 0.081(2) -0.0021(15) 0.0134(16) -0.0083(14) C17 0.0503(15) 0.0414(15) 0.0617(16) 0.0014(13) 0.0186(13) 0.0002(11) C18 0.0559(16) 0.0670(19) 0.0613(16) -0.0027(15) 0.0255(14) -0.0030(13) C19 0.0546(17) 0.073(2) 0.090(2) -0.0014(18) 0.0341(16) 0.0021(14) C20 0.0567(17) 0.0508(17) 0.0676(18) 0.0037(14) 0.0191(14) 0.0000(12) C21 0.082(2) 0.0588(19) 0.082(2) 0.0146(17) 0.0028(18) -0.0113(15) C22 0.0568(16) 0.0555(17) 0.0701(18) 0.0067(15) 0.0128(14) -0.0025(13) C23 0.067(2) 0.085(2) 0.0678(19) 0.0147(18) 0.0101(16) -0.0104(16) C24 0.0668(19) 0.065(2) 0.0636(18) 0.0033(16) 0.0183(16) 0.0017(16) O24A 0.0932(17) 0.0800(17) 0.115(2) 0.0300(16) -0.0180(16) -0.0026(13) O24B 0.0866(17) 0.105(2) 0.0833(16) 0.0240(14) 0.0023(13) -0.0356(14) N1G 0.0600(14) 0.0792(18) 0.0667(15) -0.0063(14) 0.0123(13) -0.0007(12) C1G 0.080(2) 0.070(2) 0.073(2) -0.0059(17) 0.0237(18) 0.0015(16) C2G 0.161(4) 0.186(6) 0.071(3) -0.003(3) 0.013(3) 0.040(4) C3G 0.103(4) 0.276(8) 0.086(3) -0.018(4) 0.020(3) 0.077(4) C4G 0.138(6) 0.57(2) 0.61(2) -0.469(19) 0.193(10) -0.186(10) C5G 0.233(8) 0.230(8) 0.214(7) 0.023(6) 0.130(6) 0.116(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.517(4) . ? C1 C10 1.549(4) . ? C2 C3 1.508(4) . ? O3 C3 1.434(3) . ? C3 C4 1.511(4) . ? C4 C5 1.528(4) . ? C5 C6 1.535(4) . ? C5 C10 1.558(4) . ? C6 C7 1.526(4) . ? C7 C8 1.529(4) . ? C8 C14 1.529(4) . ? C8 C9 1.543(3) . ? C9 C11 1.525(3) . ? C9 C10 1.551(3) . ? C10 C19 1.542(3) . ? C11 C12 1.532(4) . ? O12 C12 1.434(3) . ? C12 C13 1.534(3) . ? C13 C18 1.536(3) . ? C13 C14 1.542(3) . ? C13 C17 1.563(4) . ? C14 C15 1.538(4) . ? C15 C16 1.537(4) . ? C16 C17 1.546(4) . ? C17 C20 1.543(4) . ? C20 C22 1.525(4) . ? C20 C21 1.542(4) . ? C22 C23 1.512(4) . ? C23 C24 1.513(4) . ? C24 O24B 1.232(4) . ? C24 O24A 1.242(4) . ? N1G C1G 1.495(4) . ? C1G C2G 1.448(5) . ? C1G C3G 1.448(6) . ? C3G C4G 1.363(13) . ? C3G C5G 1.560(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C10 113.6(2) . . ? C3 C2 C1 109.4(2) . . ? O3 C3 C2 111.9(2) . . ? O3 C3 C4 108.2(2) . . ? C2 C3 C4 110.3(2) . . ? C3 C4 C5 113.4(2) . . ? C4 C5 C6 111.5(2) . . ? C4 C5 C10 112.9(2) . . ? C6 C5 C10 111.3(2) . . ? C7 C6 C5 112.6(2) . . ? C6 C7 C8 111.6(2) . . ? C7 C8 C14 112.3(2) . . ? C7 C8 C9 110.3(2) . . ? C14 C8 C9 109.07(19) . . ? C11 C9 C8 111.52(19) . . ? C11 C9 C10 113.1(2) . . ? C8 C9 C10 112.19(19) . . ? C19 C10 C1 106.2(2) . . ? C19 C10 C9 111.6(2) . . ? C1 C10 C9 112.3(2) . . ? C19 C10 C5 109.6(2) . . ? C1 C10 C5 107.5(2) . . ? C9 C10 C5 109.47(19) . . ? C9 C11 C12 114.6(2) . . ? O12 C12 C11 107.6(2) . . ? O12 C12 C13 111.5(2) . . ? C11 C12 C13 111.3(2) . . ? C12 C13 C18 108.4(2) . . ? C12 C13 C14 107.78(19) . . ? C18 C13 C14 113.0(2) . . ? C12 C13 C17 117.8(2) . . ? C18 C13 C17 109.6(2) . . ? C14 C13 C17 100.19(19) . . ? C8 C14 C15 118.66(19) . . ? C8 C14 C13 114.69(19) . . ? C15 C14 C13 103.8(2) . . ? C16 C15 C14 103.8(2) . . ? C15 C16 C17 107.8(2) . . ? C20 C17 C16 113.4(2) . . ? C20 C17 C13 119.5(2) . . ? C16 C17 C13 102.6(2) . . ? C22 C20 C21 110.6(2) . . ? C22 C20 C17 109.9(2) . . ? C21 C20 C17 112.5(3) . . ? C23 C22 C20 115.7(2) . . ? C22 C23 C24 116.1(3) . . ? O24B C24 O24A 120.5(3) . . ? O24B C24 C23 120.9(3) . . ? O24A C24 C23 118.6(3) . . ? C2G C1G C3G 117.4(4) . . ? C2G C1G N1G 110.4(3) . . ? C3G C1G N1G 113.6(3) . . ? C4G C3G C1G 116.3(8) . . ? C4G C3G C5G 114.4(6) . . ? C1G C3G C5G 110.3(5) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.63 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.199 _refine_diff_density_min -0.139 _refine_diff_density_rms 0.031 _chemical_name_common '(R)-3-methyl-2-butylammonium deoxycholate' data_7 _database_code_depnum_ccdc_archive 'CCDC 886464' #TrackingRef 'REVISED_CIF_DATA_OCT_2012.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (S)-3-methyl-2-butylammonium deoxycholate ; _chemical_formula_moiety ? _chemical_formula_sum 'C29 H53 N O4' _chemical_formula_weight 479.72 _chemical_absolute_configuration rm loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.026(2) _cell_length_b 7.5245(15) _cell_length_c 17.600(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.26(3) _cell_angle_gamma 90.00 _cell_volume 1408.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5015 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 25.30 _exptl_crystal_description rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.131 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9769 _exptl_absorpt_correction_T_max 0.9934 _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 1999)' _exptl_special_details ; none ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '1\% \f scans and \w scans' _diffrn_reflns_number 5015 _diffrn_reflns_av_R_equivalents 0.0496 _diffrn_reflns_av_sigmaI/netI 0.0859 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 25.30 _reflns_number_total 2760 _reflns_number_gt 1722 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0524P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef ? _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2760 _refine_ls_number_parameters 319 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0938 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.0989 _refine_ls_wR_factor_gt 0.0869 _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_restrained_S_all 0.979 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3090(3) 0.3683(5) -0.20431(19) 0.0310(9) Uani 1 1 d . . . H5A H 0.3472 0.2712 -0.1679 0.037 Uiso 1 1 calc R . . H5B H 0.3606 0.3841 -0.2421 0.037 Uiso 1 1 calc R . . C2 C 0.1772(3) 0.3110(4) -0.24997(19) 0.0306(9) Uani 1 1 d . . . H8A H 0.1821 0.1997 -0.2790 0.037 Uiso 1 1 calc R . . H8B H 0.1254 0.2879 -0.2128 0.037 Uiso 1 1 calc R . . O3 O -0.01020(19) 0.4088(3) -0.34775(13) 0.0390(7) Uani 1 1 d D . . C3 C 0.1173(3) 0.4536(4) -0.30672(19) 0.0327(9) Uani 1 1 d . . . H27 H 0.1674 0.4709 -0.3460 0.039 Uiso 1 1 calc R . . H3 H -0.1645 0.6653 0.5090 0.101(17) Uiso 1 1 d RD . . C4 C 0.1138(3) 0.6281(4) -0.2631(2) 0.0316(9) Uani 1 1 d . . . H19A H 0.0575 0.6142 -0.2280 0.038 Uiso 1 1 calc R . . H19B H 0.0782 0.7222 -0.3019 0.038 Uiso 1 1 calc R . . C5 C 0.2447(3) 0.6868(5) -0.2137(2) 0.0290(8) Uani 1 1 d . . . H10 H 0.2960 0.7108 -0.2517 0.035 Uiso 1 1 calc R . . C6 C 0.2382(3) 0.8614(5) -0.1708(2) 0.0347(9) Uani 1 1 d . . . H13A H 0.3241 0.9109 -0.1518 0.042 Uiso 1 1 calc R . . H13B H 0.1870 0.9476 -0.2083 0.042 Uiso 1 1 calc R . . C7 C 0.1819(3) 0.8394(5) -0.10116(19) 0.0317(9) Uani 1 1 d . . . H16A H 0.0924 0.8049 -0.1206 0.038 Uiso 1 1 calc R . . H16B H 0.1856 0.9545 -0.0733 0.038 Uiso 1 1 calc R . . H7 H -0.0756 0.5205 0.5423 0.043(12) Uiso 1 1 d RD . . C8 C 0.2521(3) 0.6980(4) -0.04338(19) 0.0269(8) Uani 1 1 d . . . H17 H 0.3408 0.7386 -0.0216 0.032 Uiso 1 1 calc R . . C9 C 0.2539(3) 0.5216(4) -0.08692(19) 0.0259(8) Uani 1 1 d . . . H12 H 0.1640 0.4886 -0.1106 0.031 Uiso 1 1 calc R . . C10 C 0.3151(3) 0.5388(5) -0.15687(19) 0.0264(8) Uani 1 1 d . . . C11 C 0.3108(3) 0.3717(5) -0.02958(19) 0.0283(8) Uani 1 1 d . . . H3A H 0.3001 0.2581 -0.0590 0.034 Uiso 1 1 calc R . . H3B H 0.4022 0.3934 -0.0091 0.034 Uiso 1 1 calc R . . O12 O 0.12618(17) 0.2927(3) 0.00932(14) 0.0362(6) Uani 1 1 d . . . H1 H 0.0878 0.3001 0.0446 0.043 Uiso 1 1 calc R . . C12 C 0.2536(3) 0.3521(4) 0.04009(19) 0.0251(8) Uani 1 1 d . . . H9 H 0.3017 0.2599 0.0769 0.030 Uiso 1 1 calc R . . C13 C 0.2579(3) 0.5285(5) 0.08498(19) 0.0255(8) Uani 1 1 d . . . C14 C 0.1934(3) 0.6714(4) 0.02489(19) 0.0276(9) Uani 1 1 d . . . H14 H 0.1059 0.6280 0.0012 0.033 Uiso 1 1 calc R . . C15 C 0.1815(3) 0.8317(4) 0.07681(18) 0.0317(9) Uani 1 1 d . . . H15A H 0.2582 0.9061 0.0877 0.038 Uiso 1 1 calc R . . H15B H 0.1081 0.9059 0.0509 0.038 Uiso 1 1 calc R . . H15 H -0.0755 0.5334 0.4669 0.065(12) Uiso 1 1 d RD . . C16 C 0.1644(3) 0.7498(5) 0.1524(2) 0.0357(9) Uani 1 1 d . . . H32A H 0.0796 0.7774 0.1583 0.043 Uiso 1 1 calc R . . H32B H 0.2276 0.7983 0.1985 0.043 Uiso 1 1 calc R . . C17 C 0.1813(3) 0.5447(5) 0.14694(19) 0.0292(8) Uani 1 1 d . . . H23 H 0.0962 0.4940 0.1224 0.035 Uiso 1 1 calc R . . C18 C 0.3969(3) 0.5754(5) 0.12415(19) 0.0304(9) Uani 1 1 d . . . H6A H 0.4362 0.4785 0.1593 0.046 Uiso 1 1 calc R . . H6B H 0.4009 0.6852 0.1546 0.046 Uiso 1 1 calc R . . H6C H 0.4416 0.5921 0.0834 0.046 Uiso 1 1 calc R . . C19 C 0.4544(3) 0.5891(5) -0.1275(2) 0.0357(9) Uani 1 1 d . . . H20A H 0.5008 0.4914 -0.0960 0.054 Uiso 1 1 calc R . . H20B H 0.4629 0.6965 -0.0951 0.054 Uiso 1 1 calc R . . H20C H 0.4885 0.6114 -0.1727 0.054 Uiso 1 1 calc R . . C20 C 0.2295(3) 0.4552(5) 0.2272(2) 0.0325(9) Uani 1 1 d . . . H22 H 0.3149 0.5042 0.2525 0.039 Uiso 1 1 calc R . . C21 C 0.2419(3) 0.2533(5) 0.2211(2) 0.0435(10) Uani 1 1 d . . . H25A H 0.2651 0.2015 0.2740 0.065 Uiso 1 1 calc R . . H25B H 0.3071 0.2258 0.1942 0.065 Uiso 1 1 calc R . . H25C H 0.1615 0.2034 0.1910 0.065 Uiso 1 1 calc R . . C22 C 0.1437(3) 0.4995(5) 0.28067(19) 0.0344(10) Uani 1 1 d . . . H24A H 0.1334 0.6301 0.2818 0.041 Uiso 1 1 calc R . . H24B H 0.0596 0.4474 0.2573 0.041 Uiso 1 1 calc R . . C23 C 0.1910(3) 0.4332(7) 0.3646(2) 0.0495(11) Uani 1 1 d . . . H33A H 0.2017 0.3028 0.3627 0.059 Uiso 1 1 calc R . . H33B H 0.2753 0.4850 0.3872 0.059 Uiso 1 1 calc R . . C24 C 0.1114(3) 0.4719(5) 0.4206(2) 0.0359(9) Uani 1 1 d . . . O24A O 0.1455(2) 0.4061(4) 0.48828(15) 0.0502(7) Uani 1 1 d . . . O24B O 0.0150(2) 0.5673(4) 0.39697(14) 0.0462(7) Uani 1 1 d . . . N1G N -0.1322(2) 0.5459(3) 0.50163(16) 0.0372(8) Uani 1 1 d D . . C1G C -0.2412(3) 0.4164(5) 0.4837(2) 0.0407(10) Uani 1 1 d . . . H26 H -0.2050 0.2938 0.4886 0.049 Uiso 1 1 calc R . . C2G C -0.3117(3) 0.4369(7) 0.5471(2) 0.0611(13) Uani 1 1 d . . . H30A H -0.2535 0.4174 0.5991 0.092 Uiso 1 1 calc R . . H30B H -0.3798 0.3495 0.5383 0.092 Uiso 1 1 calc R . . H30C H -0.3469 0.5570 0.5446 0.092 Uiso 1 1 calc R . . C3G C -0.3194(3) 0.4380(6) 0.4005(2) 0.0500(11) Uani 1 1 d . . . H31 H -0.2616 0.4271 0.3655 0.060 Uiso 1 1 calc R . . C4G C -0.3839(4) 0.6216(7) 0.3845(3) 0.0759(16) Uani 1 1 d . . . H34A H -0.4494 0.6304 0.4126 0.114 Uiso 1 1 calc R . . H34B H -0.4218 0.6354 0.3278 0.114 Uiso 1 1 calc R . . H34C H -0.3214 0.7154 0.4028 0.114 Uiso 1 1 calc R . . C5G C -0.4154(4) 0.2933(7) 0.3780(3) 0.0753(16) Uani 1 1 d . . . H29A H -0.3732 0.1806 0.3735 0.113 Uiso 1 1 calc R . . H29B H -0.4743 0.3221 0.3273 0.113 Uiso 1 1 calc R . . H29C H -0.4615 0.2824 0.4184 0.113 Uiso 1 1 calc R . . H4 H -0.0402 0.2934 -0.3704 0.23(4) Uiso 1 1 d RD . . 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 C1 0.0299(19) 0.030(2) 0.032(2) 0.0026(18) 0.0056(15) 0.0041(16) C2 0.0394(19) 0.024(2) 0.027(2) 0.0022(18) 0.0063(15) 0.0027(16) O3 0.0336(13) 0.0454(18) 0.0325(14) -0.0027(13) -0.0012(10) -0.0047(12) C3 0.0337(19) 0.031(2) 0.032(2) -0.0027(19) 0.0065(16) -0.0026(17) C4 0.035(2) 0.029(2) 0.030(2) 0.0088(18) 0.0054(16) 0.0022(16) C5 0.0324(19) 0.025(2) 0.032(2) 0.0036(18) 0.0120(16) -0.0028(16) C6 0.042(2) 0.026(2) 0.036(2) 0.0078(18) 0.0099(17) -0.0006(17) C7 0.0368(19) 0.022(2) 0.035(2) -0.0029(18) 0.0076(16) -0.0005(16) C8 0.0253(18) 0.021(2) 0.033(2) 0.0032(17) 0.0055(15) -0.0013(14) C9 0.0249(18) 0.021(2) 0.032(2) 0.0027(17) 0.0069(15) -0.0027(14) C10 0.0199(17) 0.025(2) 0.034(2) 0.0031(18) 0.0069(15) 0.0008(15) C11 0.0271(17) 0.027(2) 0.030(2) -0.0013(18) 0.0065(15) 0.0035(16) O12 0.0293(13) 0.0334(15) 0.0461(16) -0.0018(13) 0.0103(11) -0.0074(11) C12 0.0221(17) 0.020(2) 0.033(2) 0.0023(17) 0.0075(15) 0.0030(15) C13 0.0197(17) 0.025(2) 0.033(2) 0.0023(18) 0.0077(14) 0.0018(15) C14 0.0216(18) 0.026(2) 0.034(2) 0.0006(18) 0.0067(15) -0.0026(15) C15 0.0318(18) 0.025(2) 0.040(2) -0.0027(19) 0.0111(16) 0.0020(15) C16 0.0349(19) 0.033(2) 0.041(2) -0.0014(19) 0.0135(16) 0.0049(17) C17 0.0234(17) 0.028(2) 0.036(2) -0.0020(19) 0.0076(15) -0.0008(16) C18 0.0256(18) 0.034(2) 0.031(2) -0.0027(18) 0.0055(15) -0.0004(16) C19 0.0327(19) 0.035(2) 0.042(2) 0.0046(19) 0.0141(16) 0.0011(17) C20 0.0303(18) 0.033(2) 0.037(2) 0.0002(19) 0.0132(16) 0.0015(17) C21 0.055(2) 0.040(3) 0.040(2) 0.010(2) 0.0199(19) 0.014(2) C22 0.037(2) 0.035(2) 0.033(2) 0.0019(18) 0.0129(17) 0.0041(15) C23 0.048(2) 0.067(3) 0.038(2) 0.011(2) 0.0201(18) 0.019(2) C24 0.044(2) 0.031(2) 0.036(2) -0.003(2) 0.0158(19) 0.000(2) O24A 0.0671(17) 0.0507(19) 0.0350(16) 0.0099(15) 0.0172(13) 0.0107(15) O24B 0.0486(15) 0.0510(18) 0.0442(16) 0.0104(15) 0.0212(13) 0.0163(15) N1G 0.0305(16) 0.045(2) 0.0350(19) -0.0004(17) 0.0071(15) -0.0002(15) C1G 0.035(2) 0.041(3) 0.044(2) 0.000(2) 0.0068(17) -0.0050(18) C2G 0.050(2) 0.084(4) 0.051(3) -0.001(3) 0.016(2) -0.018(2) C3G 0.041(2) 0.070(3) 0.039(3) -0.013(2) 0.0111(18) -0.010(2) C4G 0.062(3) 0.089(4) 0.066(4) 0.022(3) -0.003(2) 0.004(3) C5G 0.055(3) 0.106(4) 0.067(3) -0.036(3) 0.020(2) -0.033(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C10 1.522(5) . ? C1 C2 1.526(4) . ? C2 C3 1.496(4) . ? O3 C3 1.441(4) . ? C3 C4 1.526(4) . ? C4 C5 1.541(4) . ? C5 C6 1.526(5) . ? C5 C10 1.561(5) . ? C6 C7 1.521(5) . ? C7 C8 1.533(4) . ? C8 C14 1.520(4) . ? C8 C9 1.536(5) . ? C9 C11 1.533(4) . ? C9 C10 1.557(4) . ? C10 C19 1.533(4) . ? C11 C12 1.526(4) . ? O12 C12 1.438(3) . ? C12 C13 1.539(5) . ? C13 C14 1.544(5) . ? C13 C18 1.546(4) . ? C13 C17 1.550(4) . ? C14 C15 1.540(5) . ? C15 C16 1.522(4) . ? C16 C17 1.561(5) . ? C17 C20 1.528(5) . ? C20 C21 1.532(5) . ? C20 C22 1.537(4) . ? C22 C23 1.515(5) . ? C23 C24 1.512(5) . ? C24 O24A 1.252(4) . ? C24 O24B 1.259(4) . ? N1G C1G 1.515(4) . ? C1G C3G 1.499(5) . ? C1G C2G 1.526(5) . ? C3G C5G 1.497(5) . ? C3G C4G 1.546(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 C1 C2 115.2(3) . . ? C3 C2 C1 109.9(3) . . ? O3 C3 C2 111.6(3) . . ? O3 C3 C4 107.6(2) . . ? C2 C3 C4 110.3(3) . . ? C3 C4 C5 112.8(3) . . ? C6 C5 C4 111.6(3) . . ? C6 C5 C10 112.2(3) . . ? C4 C5 C10 113.0(3) . . ? C7 C6 C5 112.8(3) . . ? C6 C7 C8 111.5(3) . . ? C14 C8 C7 111.7(2) . . ? C14 C8 C9 110.1(2) . . ? C7 C8 C9 109.9(3) . . ? C11 C9 C8 111.4(3) . . ? C11 C9 C10 113.2(3) . . ? C8 C9 C10 112.8(3) . . ? C1 C10 C19 106.8(3) . . ? C1 C10 C9 113.4(3) . . ? C19 C10 C9 111.0(3) . . ? C1 C10 C5 107.9(3) . . ? C19 C10 C5 109.0(3) . . ? C9 C10 C5 108.6(3) . . ? C12 C11 C9 114.6(2) . . ? O12 C12 C11 107.3(3) . . ? O12 C12 C13 110.9(2) . . ? C11 C12 C13 111.4(3) . . ? C12 C13 C14 107.6(3) . . ? C12 C13 C18 108.6(3) . . ? C14 C13 C18 111.8(3) . . ? C12 C13 C17 118.7(3) . . ? C14 C13 C17 100.9(2) . . ? C18 C13 C17 109.1(3) . . ? C8 C14 C15 119.1(3) . . ? C8 C14 C13 114.7(3) . . ? C15 C14 C13 103.6(3) . . ? C16 C15 C14 104.5(3) . . ? C15 C16 C17 107.6(3) . . ? C20 C17 C13 119.6(3) . . ? C20 C17 C16 113.4(3) . . ? C13 C17 C16 102.5(3) . . ? C17 C20 C21 112.8(3) . . ? C17 C20 C22 110.5(3) . . ? C21 C20 C22 109.8(3) . . ? C23 C22 C20 114.6(3) . . ? C24 C23 C22 117.5(3) . . ? O24A C24 O24B 123.8(3) . . ? O24A C24 C23 117.6(3) . . ? O24B C24 C23 118.6(3) . . ? C3G C1G N1G 110.8(3) . . ? C3G C1G C2G 115.5(3) . . ? N1G C1G C2G 108.1(3) . . ? C5G C3G C1G 111.4(4) . . ? C5G C3G C4G 110.0(3) . . ? C1G C3G C4G 113.2(4) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.30 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.182 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.038 ####END _chemical_name_common '(S)-3-methyl-2-butylammonium deoxycholate'