data_global #=========================================================================== _audit_creation_date '2010-04-30' _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _audit_update_record ; ; #=========================================================================== # 1. SUBMISSION DETAILS #=========================================================================== _publ_contact_author_name 'Dr Damon A. Parrish' _publ_contact_author_address ; Laboratory for the Structure of Matter Naval Research Laboratory Washington, DC 20375 ; _publ_contact_author_email 'damon.parrish@nrl.navy.mil' _publ_contact_author_fax '202-767-6874' _publ_contact_author_phone '202-404-2141' _publ_requested_journal ? _publ_requested_category ? _publ_requested_coeditor_name ? _publ_contact_letter ; ; #=========================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) # Do NOT alter anthing in this section. #=========================================================================== _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #=========================================================================== # 3. TITLE AND AUTHOR LIST #=========================================================================== _publ_section_title ; title ; loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Parrish, Damon A.' ; Laboratory for the Structure of Matter, Code 6030 Naval Research Laboratory Washington, DC 20375 ; ? 'Lakshman, Mahesh' ; Department of Chemistry The City College and The City University of New York 160 Convent Avenue New York, NY 10031 ; ? #=========================================================================== # 4. TEXT #=========================================================================== _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; ; _publ_section_references ; Bruker (2009). APEX2 v2009.3-0. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2009). SAINT v7.60A. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2008). SADABS v2008/1, Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2008). XPREP v2008/2. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2008). SHELXTL v2008/4. Bruker AXS Inc., Madison, Wisconsin, USA. ; _publ_section_figure_captions ; ; _publ_section_table_legends ; ; _publ_section_acknowledgements ; Crystallographic studies were supported in part by the Office of Naval Research (ONR) and the Naval Research Laboratory (NRL). ; #========================================================================== data_lak007 _audit_creation_date '2010-04-30' _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; 3,4-dimethoxy-8-methylbenzo[c]phenanthrene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H18 O2' _chemical_formula_sum 'C21 H18 O2' _chemical_formula_weight 302.35 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' '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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.9858(11) _cell_length_b 14.5862(14) _cell_length_c 8.9045(8) _cell_angle_alpha 90.00 _cell_angle_beta 97.0100(10) _cell_angle_gamma 90.00 _cell_volume 1545.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description irregular _exptl_crystal_colour yellow _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.6796 _exptl_absorpt_correction_T_max 0.7453 _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 SMART APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13584 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0167 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 26.09 _reflns_number_total 3039 _reflns_number_gt 2408 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2 v2009.3-0 (Bruker, 2009)' _computing_cell_refinement 'Bruker APEX2 v2009.3-0 (Bruker, 2009)' _computing_data_reduction ; Bruker SAINT v7.60A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008) ; _computing_structure_solution 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_structure_refinement 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_molecular_graphics 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_publication_material 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _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^)+(0.0606P)^2^+0.1927P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3039 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1169 _refine_ls_wR_factor_gt 0.1066 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _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 0.00360(10) 0.09100(8) 0.82158(13) 0.0423(3) Uani 1 1 d . . . C2 C -0.07079(11) 0.15542(9) 0.87812(14) 0.0459(3) Uani 1 1 d . . . C3 C -0.18103(10) 0.12950(9) 0.89843(14) 0.0473(3) Uani 1 1 d . . . C4 C -0.21837(11) 0.04100(9) 0.87061(15) 0.0493(3) Uani 1 1 d . . . C5 C -0.14262(11) -0.02473(9) 0.83000(15) 0.0489(3) Uani 1 1 d . . . H5 H -0.1651 -0.0856 0.8186 0.059 Uiso 1 1 calc R . . C6 C -0.03551(10) -0.00047(9) 0.80674(14) 0.0460(3) Uani 1 1 d . . . H6 H 0.0131 -0.0457 0.7803 0.055 Uiso 1 1 calc R . . C7 C -0.03063(12) 0.24456(10) 0.92309(17) 0.0571(4) Uani 1 1 d . . . H7 H -0.0796 0.2872 0.9569 0.069 Uiso 1 1 calc R . . C8 C 0.07727(13) 0.26750(10) 0.91709(18) 0.0590(4) Uani 1 1 d . . . H8 H 0.1032 0.3242 0.9543 0.071 Uiso 1 1 calc R . . C9 C 0.15273(11) 0.20717(9) 0.85513(15) 0.0504(3) Uani 1 1 d . . . C10 C 0.11536(10) 0.12122(9) 0.79648(14) 0.0440(3) Uani 1 1 d . . . C11 C 0.19215(10) 0.07009(9) 0.71315(14) 0.0462(3) Uani 1 1 d . . . C12 C 0.30669(11) 0.09854(10) 0.71980(16) 0.0549(4) Uani 1 1 d . . . C13 C 0.34374(12) 0.18254(11) 0.79510(18) 0.0618(4) Uani 1 1 d . . . C14 C 0.26646(12) 0.23465(11) 0.85362(18) 0.0597(4) Uani 1 1 d . . . H14 H 0.2887 0.2913 0.8950 0.072 Uiso 1 1 calc R . . C15 C 0.15765(12) -0.00303(9) 0.61414(15) 0.0518(3) Uani 1 1 d . . . H15 H 0.0821 -0.0193 0.6002 0.062 Uiso 1 1 calc R . . C16 C 0.23175(14) -0.05079(11) 0.53793(18) 0.0647(4) Uani 1 1 d . . . H16 H 0.2061 -0.0981 0.4728 0.078 Uiso 1 1 calc R . . C17 C 0.34526(15) -0.02833(13) 0.5583(2) 0.0770(5) Uani 1 1 d . . . H17 H 0.3966 -0.0634 0.5130 0.092 Uiso 1 1 calc R . . C18 C 0.38076(13) 0.04528(13) 0.6448(2) 0.0718(5) Uani 1 1 d . . . H18 H 0.4565 0.0610 0.6549 0.086 Uiso 1 1 calc R . . O19 O -0.32821(8) 0.02434(7) 0.88903(13) 0.0667(3) Uani 1 1 d . . . C20 C -0.37197(13) -0.06409(11) 0.8525(2) 0.0711(5) Uani 1 1 d . . . H20A H -0.4492 -0.0665 0.8707 0.107 Uiso 1 1 calc R . . H20B H -0.3295 -0.1089 0.9143 0.107 Uiso 1 1 calc R . . H20C H -0.3669 -0.0768 0.7478 0.107 Uiso 1 1 calc R . . O21 O -0.25207(8) 0.19547(7) 0.94471(11) 0.0578(3) Uani 1 1 d . . . C22 C -0.27155(15) 0.18690(13) 1.09919(19) 0.0748(5) Uani 1 1 d . . . H22A H -0.3192 0.2360 1.1246 0.112 Uiso 1 1 calc R . . H22B H -0.2011 0.1897 1.1632 0.112 Uiso 1 1 calc R . . H22C H -0.3074 0.1292 1.1136 0.112 Uiso 1 1 calc R . . C23 C 0.46442(14) 0.21339(14) 0.8029(3) 0.0916(6) Uani 1 1 d . . . H23A H 0.4746 0.2687 0.8614 0.137 Uiso 1 1 calc R . . H23B H 0.4826 0.2246 0.7025 0.137 Uiso 1 1 calc R . . H23C H 0.5129 0.1665 0.8499 0.137 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 0.0431(6) 0.0439(7) 0.0392(6) 0.0035(5) 0.0017(5) 0.0047(5) C2 0.0476(7) 0.0458(7) 0.0440(7) 0.0023(5) 0.0038(5) 0.0053(5) C3 0.0460(7) 0.0495(7) 0.0465(7) 0.0015(6) 0.0066(5) 0.0097(5) C4 0.0425(7) 0.0561(8) 0.0497(7) 0.0038(6) 0.0076(5) 0.0012(6) C5 0.0522(7) 0.0436(7) 0.0510(8) 0.0018(6) 0.0062(6) -0.0013(6) C6 0.0468(7) 0.0450(7) 0.0464(7) 0.0021(5) 0.0067(5) 0.0072(5) C7 0.0593(8) 0.0473(8) 0.0655(9) -0.0086(6) 0.0111(7) 0.0048(6) C8 0.0626(9) 0.0482(8) 0.0658(9) -0.0078(7) 0.0063(7) -0.0042(6) C9 0.0501(7) 0.0487(7) 0.0509(7) 0.0052(6) 0.0005(6) -0.0001(6) C10 0.0423(7) 0.0462(7) 0.0426(7) 0.0076(5) 0.0009(5) 0.0049(5) C11 0.0448(7) 0.0481(7) 0.0459(7) 0.0138(6) 0.0058(5) 0.0077(5) C12 0.0460(7) 0.0593(8) 0.0599(8) 0.0203(7) 0.0095(6) 0.0069(6) C13 0.0446(8) 0.0657(9) 0.0736(10) 0.0191(8) 0.0017(7) -0.0032(7) C14 0.0534(8) 0.0552(8) 0.0683(9) 0.0079(7) -0.0014(7) -0.0077(6) C15 0.0541(8) 0.0526(8) 0.0504(8) 0.0081(6) 0.0131(6) 0.0066(6) C16 0.0778(11) 0.0592(9) 0.0623(9) 0.0070(7) 0.0291(8) 0.0091(7) C17 0.0739(11) 0.0756(12) 0.0899(13) 0.0150(10) 0.0446(10) 0.0195(9) C18 0.0523(9) 0.0781(11) 0.0895(12) 0.0223(10) 0.0262(8) 0.0107(8) O19 0.0473(6) 0.0664(7) 0.0886(8) -0.0074(6) 0.0171(5) -0.0042(5) C20 0.0549(9) 0.0643(10) 0.0941(12) 0.0177(9) 0.0094(8) -0.0082(7) O21 0.0542(6) 0.0589(6) 0.0620(6) -0.0010(5) 0.0146(4) 0.0148(4) C22 0.0763(11) 0.0872(12) 0.0642(10) -0.0115(9) 0.0214(8) 0.0114(9) C23 0.0488(9) 0.0916(13) 0.1330(18) 0.0152(12) 0.0050(10) -0.0101(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 C1 C6 1.4150(18) . ? C1 C2 1.4287(17) . ? C1 C10 1.4531(17) . ? C2 C3 1.4071(18) . ? C2 C7 1.4267(19) . ? C3 C4 1.3787(19) . ? C3 O21 1.3808(15) . ? C4 O19 1.3682(16) . ? C4 C5 1.3979(18) . ? C5 C6 1.3715(18) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.343(2) . ? C7 H7 0.9300 . ? C8 C9 1.421(2) . ? C8 H8 0.9300 . ? C9 C10 1.4099(18) . ? C9 C14 1.4224(19) . ? C10 C11 1.4563(18) . ? C11 C15 1.413(2) . ? C11 C12 1.4285(18) . ? C12 C18 1.408(2) . ? C12 C13 1.441(2) . ? C13 C14 1.351(2) . ? C13 C23 1.508(2) . ? C14 H14 0.9300 . ? C15 C16 1.372(2) . ? C15 H15 0.9300 . ? C16 C17 1.390(2) . ? C16 H16 0.9300 . ? C17 C18 1.359(3) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? O19 C20 1.4153(19) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? O21 C22 1.4285(19) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? 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 C6 C1 C2 116.05(11) . . ? C6 C1 C10 124.95(11) . . ? C2 C1 C10 118.77(11) . . ? C3 C2 C7 119.92(12) . . ? C3 C2 C1 120.32(12) . . ? C7 C2 C1 119.64(12) . . ? C4 C3 O21 120.52(12) . . ? C4 C3 C2 121.18(12) . . ? O21 C3 C2 118.29(12) . . ? O19 C4 C3 116.15(11) . . ? O19 C4 C5 125.03(12) . . ? C3 C4 C5 118.80(12) . . ? C6 C5 C4 120.77(12) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 122.32(12) . . ? C5 C6 H6 118.8 . . ? C1 C6 H6 118.8 . . ? C8 C7 C2 120.62(13) . . ? C8 C7 H7 119.7 . . ? C2 C7 H7 119.7 . . ? C7 C8 C9 121.52(13) . . ? C7 C8 H8 119.2 . . ? C9 C8 H8 119.2 . . ? C10 C9 C8 120.40(12) . . ? C10 C9 C14 120.57(13) . . ? C8 C9 C14 119.03(13) . . ? C9 C10 C1 118.03(11) . . ? C9 C10 C11 116.88(11) . . ? C1 C10 C11 125.08(12) . . ? C15 C11 C12 116.85(12) . . ? C15 C11 C10 123.33(12) . . ? C12 C11 C10 119.61(12) . . ? C18 C12 C11 118.59(15) . . ? C18 C12 C13 120.90(14) . . ? C11 C12 C13 120.43(13) . . ? C14 C13 C12 118.10(13) . . ? C14 C13 C23 120.88(16) . . ? C12 C13 C23 120.97(15) . . ? C13 C14 C9 123.24(14) . . ? C13 C14 H14 118.4 . . ? C9 C14 H14 118.4 . . ? C16 C15 C11 122.29(14) . . ? C16 C15 H15 118.9 . . ? C11 C15 H15 118.9 . . ? C15 C16 C17 119.89(16) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C18 C17 C16 119.60(15) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C17 C18 C12 122.20(15) . . ? C17 C18 H18 118.9 . . ? C12 C18 H18 118.9 . . ? C4 O19 C20 117.99(11) . . ? O19 C20 H20A 109.5 . . ? O19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C3 O21 C22 113.93(11) . . ? O21 C22 H22A 109.5 . . ? O21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C13 C23 H23A 109.5 . . ? C13 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C13 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 C6 C1 C2 C3 -7.62(17) . . . . ? C10 C1 C2 C3 177.63(11) . . . . ? C6 C1 C2 C7 168.40(12) . . . . ? C10 C1 C2 C7 -6.36(18) . . . . ? C7 C2 C3 C4 -173.28(13) . . . . ? C1 C2 C3 C4 2.73(19) . . . . ? C7 C2 C3 O21 7.80(18) . . . . ? C1 C2 C3 O21 -176.20(11) . . . . ? O21 C3 C4 O19 1.12(19) . . . . ? C2 C3 C4 O19 -177.78(12) . . . . ? O21 C3 C4 C5 -177.38(11) . . . . ? C2 C3 C4 C5 3.7(2) . . . . ? O19 C4 C5 C6 176.66(12) . . . . ? C3 C4 C5 C6 -5.0(2) . . . . ? C4 C5 C6 C1 -0.3(2) . . . . ? C2 C1 C6 C5 6.50(18) . . . . ? C10 C1 C6 C5 -179.11(11) . . . . ? C3 C2 C7 C8 174.00(14) . . . . ? C1 C2 C7 C8 -2.0(2) . . . . ? C2 C7 C8 C9 5.0(2) . . . . ? C7 C8 C9 C10 0.6(2) . . . . ? C7 C8 C9 C14 -179.16(14) . . . . ? C8 C9 C10 C1 -8.96(18) . . . . ? C14 C9 C10 C1 170.84(12) . . . . ? C8 C9 C10 C11 170.23(12) . . . . ? C14 C9 C10 C11 -9.98(18) . . . . ? C6 C1 C10 C9 -162.61(12) . . . . ? C2 C1 C10 C9 11.64(17) . . . . ? C6 C1 C10 C11 18.28(19) . . . . ? C2 C1 C10 C11 -167.47(11) . . . . ? C9 C10 C11 C15 -162.13(12) . . . . ? C1 C10 C11 C15 16.99(19) . . . . ? C9 C10 C11 C12 12.43(17) . . . . ? C1 C10 C11 C12 -168.45(11) . . . . ? C15 C11 C12 C18 -8.39(18) . . . . ? C10 C11 C12 C18 176.70(12) . . . . ? C15 C11 C12 C13 168.43(12) . . . . ? C10 C11 C12 C13 -6.48(18) . . . . ? C18 C12 C13 C14 174.34(14) . . . . ? C11 C12 C13 C14 -2.4(2) . . . . ? C18 C12 C13 C23 -3.2(2) . . . . ? C11 C12 C13 C23 -179.99(14) . . . . ? C12 C13 C14 C9 5.2(2) . . . . ? C23 C13 C14 C9 -177.24(15) . . . . ? C10 C9 C14 C13 1.2(2) . . . . ? C8 C9 C14 C13 -178.98(14) . . . . ? C12 C11 C15 C16 5.95(19) . . . . ? C10 C11 C15 C16 -179.35(12) . . . . ? C11 C15 C16 C17 0.7(2) . . . . ? C15 C16 C17 C18 -4.9(2) . . . . ? C16 C17 C18 C12 2.2(2) . . . . ? C11 C12 C18 C17 4.6(2) . . . . ? C13 C12 C18 C17 -172.21(15) . . . . ? C3 C4 O19 C20 176.11(13) . . . . ? C5 C4 O19 C20 -5.5(2) . . . . ? C4 C3 O21 C22 75.10(17) . . . . ? C2 C3 O21 C22 -105.97(15) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.09 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.126 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.032