#------------------------------------------------------------------------------ #$Date: 2015-04-02 12:22:18 +0100 (Thu, 02 Apr 2015) $ #$Revision: 134621 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/03/2010344.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2010344 loop_ _publ_author_name 'De Ridder, Dirk J. A.' 'Fraanje, Jan' 'Goubitz, Kees' 'Schenk, Henk' _publ_contact_author ; Dr. Dirk J.A. De Ridder Commission of the European Communities - Joint Research Centre European Institute for Transuranium Elements Postfach 2340 D-76125 Karlsruhe Germany ; _publ_section_title ; Crystal studies of musk compounds. XIII. Molecular structures of 6-formyl-1,1,2,4,4,7-hexamethyltetralin (I) and 6-formyl-1,1,4,4,5,7-hexamethyltetralin (2) ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1962 _journal_page_last 1966 _journal_paper_doi 10.1107/S0108270194002647 _journal_volume 50 _journal_year 1994 _chemical_formula_moiety 'C17 H24 O' _chemical_formula_sum 'C17 H24 O' _chemical_formula_weight 244.38 _chemical_melting_point .92E-91 _chemical_name_systematic 6-formyl-1,1,4,4,5,7-hexamethyltetralin _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _audit_creation_method from_xtal_archive_file_using_CIFIO _cell_angle_alpha 90.00000 _cell_angle_beta 95.630(9) _cell_angle_gamma 90.00000 _cell_formula_units_Z 4 _cell_length_a 10.3660(10) _cell_length_b 8.7150(10) _cell_length_c 15.984(2) _cell_measurement_reflns_used 23 _cell_measurement_temperature 252 _cell_measurement_theta_max 43.8 _cell_measurement_theta_min 40.0 _cell_volume 1437.0(3) _computing_cell_refinement 'CELCON comparable to Xtal LATCON' _computing_data_collection 'CAD-4 software (Enraf-Nonius, 1989)' _computing_data_reduction ; Xtal SORTRF (Hall, Spadaccini & Stewart, 1990) and Xtal ADDREF (Davenport & Hall, 1990) ; _computing_molecular_graphics 'PEANUT (Hummel, Hauser & B\"urgi, 1990)' _computing_publication_material ; Xtal BONDLA (Dreissig, Doherty, Stewart & Hall, 1990) and Xtal CIFIO (Hall, 1990) ; _computing_structure_refinement 'Xtal CRYLSQ (Olthof-Hazekamp, 1990)' _computing_structure_solution 'Xtal SIMPEL (Schenk & Hall, 1990)' _diffrn_ambient_temperature 252.0(10) _diffrn_measurement_device 'Enraf-Nonius CAD-4 diffractometer' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source xray_tube _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents 'Not available' _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 2671 _diffrn_reflns_reduction_process perpendicular_monochr_Lp _diffrn_reflns_theta_max 64.84 _diffrn_reflns_theta_min 4.29 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 60 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu .484 _exptl_absorpt_correction_T_max 1.34 _exptl_absorpt_correction_T_min .45 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'DIFABS (Walker & Stuart, 1983)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.13 _exptl_crystal_density_meas ? _exptl_crystal_description 'block shaped crystal' _exptl_crystal_F_000 536 _exptl_crystal_size_max .35 _exptl_crystal_size_mid .25 _exptl_crystal_size_min .15 _refine_diff_density_max .401 _refine_diff_density_min -.517 _refine_ls_abs_structure_details none _refine_ls_abs_structure_Flack 0 _refine_ls_extinction_coef .00000 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all .235 _refine_ls_goodness_of_fit_obs .235 _refine_ls_hydrogen_treatment ; Only coordinates of H atoms refined, restrained at 1.09 \%A to their carrier atom with fixed U~eq~=0.08 \%A^2^. The angles of the H atoms attached to C2 and C3 were restrained at 109 \%. H16 (A & B) were not refined ; _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 241 _refine_ls_number_reflns 2053 _refine_ls_number_restraints 35 _refine_ls_R_factor_all .099 _refine_ls_R_factor_obs .099 _refine_ls_shift/esd_max .389 _refine_ls_shift/esd_mean .041 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w=1/(7.52 + F~obs~ + 0.0046 F^2^~obs~)' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .117 _refine_ls_wR_factor_obs .117 _reflns_number_observed 2053 _reflns_number_total 2428 _reflns_observed_criterion refl_observed_if_Inet_>_2.5__sigma(Inet) _[local]_cod_data_source_file sh1094.cif _[local]_cod_data_source_block 2 _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; Site occupancies and disorder asseblies were reconstructed from the authors' comments that were (semantically incorrectly) included into coordinate list: Population parameter of O1A = 0.69 . . Population parameter of O1B = 0.31 . . The comments are present in the original paper supplementary CIF file, sh1094.cif (http://scripts.iucr.org/cgi-bin/sendcif?sh1094sup1) Antanas Vaitkus 2015.02.14 The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'Not available' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'w=1/(7.52 + F~obs~ + 0.0046 F^2^~obs~)' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w=1/(7.52 + F~obs~ + 0.0046 F^2^~obs~)'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2010344 loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,1/2+y,1/2-z -x,-y,-z +x,1/2-y,1/2+z loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 .046(2) .056(2) .057(2) .003(2) -.0010(10) .004(2) C2 .060(3) .143(5) .137(5) .031(3) .036(3) .072(4) C3 .069(3) .260(10) .260(10) .046(5) .074(5) .192(9) C4 .062(2) .055(2) .050(2) -.005(2) .010(2) .006(2) C5 .052(2) .049(2) .055(2) .004(2) -.0030(10) -.002(2) C6 .043(2) .055(2) .061(2) -.002(2) .0040(10) -.017(2) C7 .055(2) .057(2) .048(2) -.011(2) .0120(10) -.011(2) C8 .059(2) .052(2) .045(2) -.006(2) .0040(10) .0020(10) C9 .046(2) .045(2) .040(2) -.0030(10) .0000(10) -.0040(10) C10 .050(2) .041(2) .041(2) -.0040(10) .0000(10) -.0030(10) C11 .067(3) .063(3) .128(4) .016(2) -.004(3) -.013(3) C12 .065(3) .110(4) .080(3) .015(3) -.022(2) -.015(3) C14 .144(5) .107(4) .053(2) -.052(4) .026(3) -.009(3) C15 .145(5) .075(3) .085(3) -.053(3) .037(3) -.006(3) C16 .061(3) .082(3) .101(3) .005(2) .008(2) -.010(3) C18 .074(3) .091(3) .067(3) -.018(3) .027(2) -.004(2) C19 .079(3) .105(4) .106(4) .033(3) .009(3) .042(3) O1A .071(3) .155(6) .136(5) .035(4) -.004(3) .032(4) O1B .059(7) .150(10) .22(2) -.016(8) .036(9) -.040(10) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 .8528(3) .7386(4) .4081(2) .053(2) Uani ? ? 1.0 . . C2 .9362(5) .8077(8) .3465(4) .111(4) Uani ? ? 1.0 . . C3 .9007(5) .925(1) .3028(6) .191(8) Uani ? ? 1.0 . . C4 .7709(4) .9932(4) .2824(2) .055(2) Uani ? ? 1.0 . . C5 .5434(3) .9655(4) .3336(2) .053(2) Uani ? ? 1.0 . . C6 .4584(3) .9024(4) .3890(2) .053(2) Uani ? ? 1.0 . . C7 .5021(3) .7905(4) .4473(2) .053(2) Uani ? ? 1.0 . . C8 .6283(3) .7444(4) .4493(2) .052(2) Uani ? ? 1.0 . . C9 .7158(3) .8043(4) .3968(2) .044(2) Uani ? ? 1.0 . . C10 .6744(3) .9191(4) .3382(2) .044(2) Uani ? ? 1.0 . . C11 .8512(5) .5652(6) .3938(4) .087(3) Uani ? ? 1.0 . . C12 .9146(5) .7703(7) .4974(3) .087(3) Uani ? ? 1.0 . . C14 .7342(7) .9701(8) .1887(3) .100(4) Uani ? ? 1.0 . . C15 .7862(7) 1.1658(6) .3002(4) .100(4) Uani ? ? 1.0 . . C16 .3220(5) .9529(6) .3881(3) .081(3) Uani ? ? 1.0 . . C18 .4170(5) .7170(6) .5085(3) .076(3) Uani ? ? 1.0 . . C19 .4870(5) 1.0834(7) .2712(4) .097(4) Uani ? ? 1.0 . . O1A .2540(5) 1.0239(8) .3382(4) .121(5) Uani ? ? 0.69 1 A O1B .237(1) .890(2) .416(1) .14(1) Uani ? ? 0.31 1 B H21 1.037(3) .794(4) .362(2) .08 Uiso calc C2 1.0 . . H22 .913(4) .734(4) .290(2) .08 Uiso calc C2 1.0 . . H31 .945(3) 1.001(3) .328(2) .08 Uiso calc C3 1.0 . . H32 .940(3) .917(4) .243(2) .08 Uiso calc C3 1.0 . . H8 .662(4) .667(5) .494(2) .08 Uiso calc C8 1.0 . . H111 .797(4) .539(5) .339(2) .08 Uiso calc C11 1.0 . . H112 .951(4) .531(5) .398(3) .08 Uiso calc C11 1.0 . . H113 .782(4) .508(5) .422(3) .08 Uiso calc C11 1.0 . . H121 1.013(4) .746(5) .503(3) .08 Uiso calc C12 1.0 . . H122 .904(4) .883(5) .516(3) .08 Uiso calc C12 1.0 . . H123 .858(4) .711(5) .537(3) .08 Uiso calc C12 1.0 . . H141 .801(4) 1.009(5) .155(3) .08 Uiso calc C14 1.0 . . H142 .740(4) .859(5) .179(3) .08 Uiso calc C14 1.0 . . H143 .644(4) .959(6) .175(3) .08 Uiso calc C14 1.0 . . H151 .799(4) 1.190(5) .361(2) .08 Uiso calc C15 1.0 . . H152 .858(4) 1.217(5) .270(3) .08 Uiso calc C15 1.0 . . H153 .704(4) 1.201(6) .274(3) .08 Uiso calc C15 1.0 . . H16A .27435 .91788 .44355 .08 Uiso calc C16 0.69 1 A H16B .29668 1.06179 .35761 .08 Uiso calc C16 0.31 1 B H181 .329(4) .668(5) .480(3) .08 Uiso calc C18 1.0 . . H182 .480(4) .646(5) .547(3) .08 Uiso calc C18 1.0 . . H183 .366(4) .794(5) .540(3) .08 Uiso calc C18 1.0 . . H191 .457(4) 1.172(5) .304(3) .08 Uiso calc C19 1.0 . . H192 .523(4) 1.072(5) .213(2) .08 Uiso calc C19 1.0 . . H193 .386(4) 1.059(5) .253(3) .08 Uiso calc C19 1.0 . . loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C .017 .009 International_Tables_Vol_IV_Table_2.2B O .047 .032 International_Tables_Vol_IV_Table_2.2B H 0 0 International_Tables_Vol_IV_Table_2.2B loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 0 -4 1 1 -1 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2 C1 C9 111.2(3) yes C2 C1 C11 107.3(4) yes C2 C1 C12 108.9(4) yes C9 C1 C11 110.9(3) yes C9 C1 C12 110.1(3) yes C11 C1 C12 108.4(4) yes C1 C2 C3 122.0(5) yes C1 C2 H21 115(2) no C1 C2 H22 102(2) no C3 C2 H21 117(2) no C3 C2 H22 90(2) no H21 C2 H22 105(3) no C2 C3 C4 130.7(6) yes C2 C3 H31 104(2) no C2 C3 H32 109(2) no C4 C3 H31 103(2) no C4 C3 H32 104(2) no H31 C3 H32 104(3) no C3 C4 C10 109.4(4) yes C3 C4 C14 107.3(5) yes C3 C4 C15 106.1(5) yes C10 C4 C14 113.6(4) yes C10 C4 C15 111.3(4) yes C14 C4 C15 108.8(4) yes C6 C5 C10 120.6(3) yes C6 C5 C19 116.9(3) yes C10 C5 C19 122.5(4) yes C5 C6 C7 120.5(3) yes C5 C6 C16 122.0(3) yes C7 C6 C16 117.5(4) yes C6 C7 C8 118.0(3) yes C6 C7 C18 123.6(3) yes C8 C7 C18 118.4(3) yes C7 C8 C9 123.6(3) yes C7 C8 H8 118(2) no C9 C8 H8 118(2) no C1 C9 C8 116.1(3) yes C1 C9 C10 124.4(3) yes C8 C9 C10 119.5(3) yes C4 C10 C5 121.6(3) yes C4 C10 C9 120.5(3) yes C5 C10 C9 117.9(3) yes C1 C11 H111 110(3) no C1 C11 H112 105(2) no C1 C11 H113 115(2) no H111 C11 H112 116(3) no H111 C11 H113 85(3) no H112 C11 H113 124(3) no C1 C12 H121 112(2) no C1 C12 H122 113(2) no C1 C12 H123 106(2) no H121 C12 H122 107(3) no H121 C12 H123 117(3) no H122 C12 H123 103(3) no C4 C14 H141 112(2) no C4 C14 H142 106(3) no C4 C14 H143 112(3) no H141 C14 H142 102(4) no H141 C14 H143 131(4) no H142 C14 H143 86(4) no C4 C15 H151 113(3) no C4 C15 H152 114(2) no C4 C15 H153 99(3) no H151 C15 H152 110(3) no H151 C15 H153 113(4) no H152 C15 H153 108(4) no C6 C16 O1A 131.8(5) yes C6 C16 O1B 127.9(9) yes C6 C16 H16A 114.5(4) no C6 C16 H16B 116.9(4) no O1A C16 H16A 113.8(5) no O1B C16 H16B 115.1(9) no C7 C18 H181 114(2) no C7 C18 H182 105(2) no C7 C18 H183 113(2) no H181 C18 H182 118(3) no H181 C18 H183 91(3) no H182 C18 H183 115(3) no C5 C19 H191 107(2) no C5 C19 H192 112(2) no C5 C19 H193 110(2) no H191 C19 H192 134(4) no H191 C19 H193 87(3) no H192 C19 H193 100(3) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 . . 1.500(7) yes C1 C9 . . 1.525(5) yes C1 C11 . . 1.528(6) yes C1 C12 . . 1.530(6) yes C2 C3 . . 1.270(10) yes C2 H21 . . 1.06(3) no C2 H22 . . 1.11(3) no C3 C4 . . 1.478(7) yes C3 H31 . . .88(3) no C3 H32 . . 1.07(3) no C4 C10 . . 1.545(5) yes C4 C14 . . 1.522(6) yes C4 C15 . . 1.536(7) yes C5 C6 . . 1.420(5) yes C5 C10 . . 1.412(5) yes C5 C19 . . 1.509(7) yes C6 C7 . . 1.394(5) yes C6 C16 . . 1.479(6) yes C7 C8 . . 1.367(5) yes C7 C18 . . 1.521(6) yes C8 C9 . . 1.397(5) yes C8 H8 . . 1.02(4) no C9 C10 . . 1.408(4) yes C11 H111 . . 1.02(4) no C11 H112 . . 1.07(4) no C11 H113 . . 1.02(4) no C12 H121 . . 1.03(4) no C12 H122 . . 1.03(4) no C12 H123 . . 1.04(4) no C14 H141 . . .98(4) no C14 H142 . . .98(4) no C14 H143 . . .95(4) no C15 H151 . . .99(4) no C15 H152 . . 1.02(4) no C15 H153 . . .97(4) no C16 O1A . . 1.186(8) yes C16 O1B . . 1.16(2) yes C16 H16A . . 1.099(5) no C16 H16B . . 1.087(5) no C18 H181 . . 1.07(4) no C18 H182 . . 1.06(4) no C18 H183 . . 1.02(4) no C19 H191 . . 1.00(4) no C19 H192 . . 1.04(4) no C19 H193 . . 1.08(4) no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag C6 C8 2.366(5) . no C6 O1B 2.380(10) . no C3 C15 2.410(10) . no C5 C9 2.416(5) . no C3 C14 2.420(10) . no C8 C10 2.422(5) . no C1 C3 2.430(10) . no C7 C9 2.435(5) . no C6 O1A 2.436(7) . no C2 C11 2.439(9) . no C5 C7 2.443(5) . no C7 C16 2.457(6) . no C6 C10 2.460(5) . no C2 C12 2.466(9) . no C3 C10 2.468(7) . no C1 C8 2.480(5) . no C11 C12 2.480(8) . no C8 C18 2.482(6) . no C14 C15 2.488(8) . no C2 C9 2.495(6) . no C6 C19 2.496(8) . no C2 C4 2.501(7) . no C9 C12 2.503(6) . no C9 C11 2.515(6) . no C5 C16 2.535(6) . no C10 C15 2.544(7) . no C10 C19 2.562(7) . no C4 C9 2.565(5) . no C10 C14 2.566(6) . no C6 C18 2.570(6) . no C4 C5 2.582(5) . no C1 C10 2.596(5) . no O1B C18 2.72(2) . no C5 C8 2.756(5) . no C3 C9 2.757(9) . no O1A C19 2.785(8) . no C6 C9 2.793(4) . no C7 C10 2.846(5) . no C2 C10 2.873(6) . no C7 O1B 2.870(10) . no C16 C19 2.887(8) . no C16 C18 2.920(7) . no C8 C11 2.994(7) . no C8 C12 3.000(6) . no C4 C19 3.034(7) . no C5 O1A 3.050(6) . no C1 C4 3.057(5) . no C5 C15 3.152(8) . no C14 C19 3.153(9) . no C15 C19 3.173(9) . no C5 C14 3.190(7) . no C2 O1B 3.290(10) 1_655 no C3 C12 3.380(10) . no C2 C14 3.422(8) . no C3 C11 3.520(10) . no C2 C15 3.532(9) . no C7 O1A 3.594(7) . no C5 O1B 3.610(10) . no C9 C15 3.614(7) . no C10 C12 3.620(6) . no C9 C14 3.648(6) . no C10 C11 3.652(6) . no C12 O1B 3.68(2) 3_676 no C8 C16 3.703(6) 3_676 no C8 C16 3.706(6) . no C10 C19 3.721(7) 2_645 no C5 C19 3.726(7) 2_645 no C6 C7 3.737(5) 3_676 no C5 C18 3.741(6) 3_676 no C3 O1A 3.751(8) 1_655 no C12 O1A 3.753(9) 3_676 no C2 C8 3.771(7) . no C9 C19 3.772(7) 2_645 no C1 C7 3.776(5) . no C11 O1A 3.778(9) 2_645 no C7 C16 3.782(6) 3_676 no C3 O1B 3.780(10) 1_655 no C7 C19 3.792(7) . no C3 C5 3.801(7) . no C9 C18 3.801(6) . no C2 O1A 3.808(8) 1_655 no C11 C15 3.823(8) 1_545 no C15 O1A 3.824(9) 2_655 no C10 C16 3.826(6) . no C9 C19 3.826(7) . no C4 C8 3.844(5) . no C12 O1B 3.85(2) 1_655 no C1 C5 3.856(5) . no C6 C19 3.859(8) 2_645 no C6 C18 3.865(6) 3_676 no C5 C18 3.865(6) . no C8 C19 3.872(7) 2_645 no C4 C6 3.886(5) . no C14 O1A 3.920(10) 2_645 no C7 C19 3.943(7) 2_645 no C6 C6 3.953(5) 3_676 no C15 O1B 3.96(2) 2_655 no C18 C19 3.966(8) 3_676 no C15 C16 3.990(8) 2_655 no C9 O1B 3.99(2) 3_676 no C14 C18 4.006(7) 2_655 no C12 C16 4.008(8) 3_676 no O1B C19 4.01(2) . no C15 C18 4.012(8) 3_676 no C8 O1B 4.01(2) 3_676 no C7 C7 4.023(5) 3_676 no C8 O1A 4.037(7) 3_676 no C14 O1B 4.05(2) 2_655 no O1A C18 4.064(8) . no C2 C15 4.078(9) 2_745 no C11 C12 4.080(8) 3_766 no C9 C16 4.089(6) 3_676 no C4 C12 4.098(6) . no C8 C18 4.112(7) 3_666 no C1 C14 4.128(6) . no C11 C18 4.131(8) 3_666 no C1 C15 4.132(7) . no C3 C8 4.152(9) . no C14 C19 4.161(9) 2_645 no C5 C7 4.163(5) 3_676 no C10 C18 4.173(6) 3_676 no C6 C8 4.173(5) 3_676 no C18 C18 4.176(8) 3_666 no C16 C18 4.177(7) 3_676 no C11 C19 4.178(8) 2_645 no C7 C14 4.181(7) 2_645 no C4 C11 4.181(6) . no C2 C16 4.185(7) 1_655 no C1 O1B 4.190(10) 1_655 no C2 O1A 4.192(9) 2_645 no C6 C16 4.227(6) 3_676 no C8 O1B 4.230(10) . no C8 C19 4.262(7) . no C9 C16 4.272(6) . no C7 C12 4.276(6) . no C10 O1B 4.28(2) 3_676 no C7 C11 4.276(6) . no C6 C15 4.281(7) 2_645 no C2 C5 4.284(6) . no C12 C14 4.285(8) 4_565 no C12 C15 4.293(8) 3_776 no C8 C14 4.303(6) 4_565 no C1 C6 4.313(5) . no C7 O1B 4.31(2) 3_676 no C10 C18 4.365(6) . no C7 O1A 4.367(7) 3_676 no C12 C12 4.375(9) 3_776 no C3 O1A 4.380(10) 2_645 no C6 C14 4.386(8) 2_645 no C4 C7 4.390(5) . no C1 O1A 4.401(7) 2_645 no C3 C15 4.400(10) 2_745 no C14 C16 4.406(8) 2_655 no C7 C18 4.417(7) 3_676 no C19 C19 4.422(9) 2_645 no C19 C19 4.422(9) 2_655 no C3 C11 4.420(10) 2_755 no 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_publ_flag C9 C1 C2 C3 12.0(8) no C9 C1 C2 H21 162(2) no C9 C1 C2 H22 -85(2) no C11 C1 C2 C3 133.4(7) no C11 C1 C2 H21 -76(2) no C11 C1 C2 H22 36(2) no C12 C1 C2 C3 -109.5(7) no C12 C1 C2 H21 41(2) no C12 C1 C2 H22 153(2) no C2 C1 C9 C8 178.0(4) no C2 C1 C9 C10 -2.3(5) no C11 C1 C9 C8 58.8(4) no C11 C1 C9 C10 -121.6(4) no C12 C1 C9 C8 -61.2(4) no C12 C1 C9 C10 118.5(4) no C2 C1 C11 H111 -72(3) no C2 C1 C11 H112 54(2) no C2 C1 C11 H113 -167(3) no C9 C1 C11 H111 49(3) no C9 C1 C11 H112 176(2) no C9 C1 C11 H113 -45(3) no C12 C1 C11 H111 170(3) no C12 C1 C11 H112 -63(2) no C12 C1 C11 H113 76(3) no C2 C1 C12 H121 -47(3) no C2 C1 C12 H122 74(3) no C2 C1 C12 H123 -175(3) no C9 C1 C12 H121 -169(3) no C9 C1 C12 H122 -48(3) no C9 C1 C12 H123 63(3) no C11 C1 C12 H121 70(3) no C11 C1 C12 H122 -170(3) no C11 C1 C12 H123 -58(3) no C1 C2 C3 C4 -18.0(10) no C1 C2 C3 H31 103(2) no C1 C2 C3 H32 -148(2) no H21 C2 C3 C4 -168(2) no H21 C2 C3 H31 -47(3) no H21 C2 C3 H32 63(3) no H22 C2 C3 C4 86(2) no H22 C2 C3 H31 -153(3) no H22 C2 C3 H32 -44(3) no C2 C3 C4 C10 12.0(10) no C2 C3 C4 C14 -112.0(10) no C2 C3 C4 C15 131.8(9) no H31 C3 C4 C10 -110(2) no H31 C3 C4 C14 127(2) no H31 C3 C4 C15 10(2) no H32 C3 C4 C10 142(2) no H32 C3 C4 C14 19(2) no H32 C3 C4 C15 -98(2) no C3 C4 C10 C5 178.4(5) no C3 C4 C10 C9 -.5(6) no C14 C4 C10 C5 -61.8(5) no C14 C4 C10 C9 119.4(4) no C15 C4 C10 C5 61.5(4) no C15 C4 C10 C9 -117.4(4) no C3 C4 C14 H141 -53(3) no C3 C4 C14 H142 56(3) no C3 C4 C14 H143 149(3) no C10 C4 C14 H141 -174(3) no C10 C4 C14 H142 -65(3) no C10 C4 C14 H143 28(3) no C15 C4 C14 H141 61(3) no C15 C4 C14 H142 171(3) no C15 C4 C14 H143 -97(3) no C3 C4 C15 H151 -72(3) no C3 C4 C15 H152 54(2) no C3 C4 C15 H153 168(3) no C10 C4 C15 H151 46(3) no C10 C4 C15 H152 172(2) no C10 C4 C15 H153 -73(3) no C14 C4 C15 H151 172(3) no C14 C4 C15 H152 -62(2) no C14 C4 C15 H153 53(3) no C10 C5 C6 C7 -1.8(5) no C10 C5 C6 C16 177.5(4) no C19 C5 C6 C7 178.6(4) no C19 C5 C6 C16 -2.0(6) no C6 C5 C10 C4 -176.2(3) no C6 C5 C10 C9 2.7(5) no C19 C5 C10 C4 3.3(5) no C19 C5 C10 C9 -177.8(4) no C6 C5 C19 H191 62(3) no C6 C5 C19 H192 -142(3) no C6 C5 C19 H193 -32(3) no C10 C5 C19 H191 -118(3) no C10 C5 C19 H192 39(3) no C10 C5 C19 H193 149(2) no C5 C6 C7 C8 .1(5) no C5 C6 C7 C18 -179.7(4) no C16 C6 C7 C8 -179.2(4) no C16 C6 C7 C18 .9(6) no C5 C6 C16 O1A 15.3(9) no C5 C6 C16 O1B 162.0(10) no C5 C6 C16 H16A -165.2(4) no C5 C6 C16 H16B -17.9(6) no C7 C6 C16 O1A -165.4(6) no C7 C6 C16 O1B -18.0(10) no C7 C6 C16 H16A 14.1(6) no C7 C6 C16 H16B 161.5(4) no C6 C7 C8 C9 .6(5) no C6 C7 C8 H8 177(3) no C18 C7 C8 C9 -179.5(3) no C18 C7 C8 H8 -3(3) no C6 C7 C18 H181 54(3) no C6 C7 C18 H182 -175(2) no C6 C7 C18 H183 -49(2) no C8 C7 C18 H181 -126(2) no C8 C7 C18 H182 5(2) no C8 C7 C18 H183 132(2) no C7 C8 C9 C1 180.0(3) no C7 C8 C9 C10 .3(5) no H8 C8 C9 C1 4(3) no H8 C8 C9 C10 -176(3) no C1 C9 C10 C4 -2.7(5) no C1 C9 C10 C5 178.4(3) no C8 C9 C10 C4 176.9(3) no C8 C9 C10 C5 -2.0(5) no