# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_contact_author_name 'Yufit, Dmitry S.' _publ_contact_author_address ; Department of Chemistry University of Durham, South Rd., Durham DH1 3LE UK ; _publ_contact_author_phone '0191 334 2004' _publ_contact_author_fax '0191 384 4737' _publ_contact_author_email d.s.yufit@durham.ac.uk _publ_contact_letter ; The CIF file contains data for the structures 6aa, 6ae, 7aa, 8aa and 8ah from the paper Ruthenium-catalyzed C-H/O-H and C-H/N-H bond functiolizations: oxidative annulations of cyclopropyl-substituted alkynes by M.Deponti, S.I.Kozhushkov, D.Yufit and L.Ackermann The paper will be submitted to Org.Biomol.Chem. ; loop_ _publ_author_name _publ_author_address M.Deponti ; Institut f\"ur Organische und Biomolekulare Chemie der Georg-August-Universit\"at G\"ottingen, Tammannstrasse 2 G\"ottingen D-37077 Germany ; S.I.Kozhushkov ; Institut f\"ur Organische und Biomolekulare Chemie der Georg-August-Universit\"at G\"ottingen, Tammannstrasse 2 G\"ottingen D-37077 Germany ; D.S.Yufit ; Department of Chemistry Durham University South Rd. Durham DH1 3LE UK ; L.Ackermann ; Institut f\"ur Organische und Biomolekulare Chemie der Georg-August-Universit\"at G\"ottingen, Tammannstrasse 2 G\"ottingen D-37077 Germany ; #data data_6aa_dk79 _database_code_depnum_ccdc_archive 'CCDC 901337' #TrackingRef '- OBC_026250.cif' _audit_creation_date 2012-03-07 _audit_creation_method ; Olex2 1.2-beta (compiled 2012.01.17 svn.r2163, GUI svn.r4036) ; _chemical_name_common 4-cyclopropyl-3-phenyl-1H-isochromen-1-one _chemical_name_systematic ; 4-cyclopropyl-3-phenyl-1H-isochromen-1-one ; _chemical_formula_moiety 'C18 H14 O2' _chemical_formula_sum 'C18 H14 O2' _chemical_formula_weight 262.29 _chemical_melting_point '115-117 C' 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' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.7506(12) _cell_length_b 10.3408(6) _cell_length_c 14.2419(8) _cell_angle_alpha 90.00 _cell_angle_beta 124.7190(10) _cell_angle_gamma 90.00 _cell_volume 2632.9(3) _cell_formula_units_Z 8 _cell_measurement_reflns_used 6519 _cell_measurement_temperature 120 _cell_measurement_theta_max 30.99 _cell_measurement_theta_min 2.28 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1104 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.4 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 3 sets of \w scans each set at different \f and/or 2\q angles and each scan (3 s exposure) covering -0.300\% degrees in \w. The crystal to detector distance was 4.85 cm. ; _diffrn_reflns_av_R_equivalents 0.0498 _diffrn_reflns_av_unetI/netI 0.0307 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 14905 _diffrn_reflns_theta_full 30.00 _diffrn_reflns_theta_max 30.00 _diffrn_reflns_theta_min 2.28 _diffrn_ambient_temperature 120 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_target Mo _diffrn_source_type 'sealed X-ray tube' _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3098 _reflns_number_total 3844 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.352 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.045 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 237 _refine_ls_number_reflns 3844 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0389 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.5000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1094 _refine_ls_wR_factor_ref 0.1170 _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. ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 O1 O 0.36394(4) 0.63532(6) 0.23542(6) 0.02582(16) Uani 1 1 d . . . O2 O 0.45372(4) 0.78128(7) 0.30607(7) 0.03258(18) Uani 1 1 d . . . C1 C 0.38554(5) 0.40979(8) 0.28250(7) 0.02147(18) Uani 1 1 d . . . C2 C 0.33830(5) 0.50979(9) 0.22669(7) 0.02279(18) Uani 1 1 d . . . C3 C 0.43838(5) 0.66821(9) 0.30250(8) 0.02455(19) Uani 1 1 d . . . C4 C 0.49140(5) 0.56310(8) 0.36327(7) 0.02239(18) Uani 1 1 d . . . C5 C 0.56799(5) 0.59194(10) 0.43027(8) 0.0262(2) Uani 1 1 d . . . C6 C 0.61950(5) 0.49466(10) 0.48925(8) 0.0279(2) Uani 1 1 d . . . C7 C 0.59494(5) 0.36818(10) 0.48294(8) 0.0275(2) Uani 1 1 d . . . C8 C 0.51923(5) 0.33907(9) 0.41725(8) 0.02464(19) Uani 1 1 d . . . C9 C 0.46570(5) 0.43626(8) 0.35481(7) 0.02114(18) Uani 1 1 d . . . C10 C 0.36006(5) 0.27360(8) 0.27336(8) 0.02364(18) Uani 1 1 d . . . C11 C 0.38071(6) 0.17341(10) 0.21847(9) 0.0314(2) Uani 1 1 d . . . C12 C 0.30080(6) 0.21438(10) 0.16052(9) 0.0349(2) Uani 1 1 d . . . C13 C 0.25564(5) 0.50943(9) 0.14842(8) 0.02493(19) Uani 1 1 d . . . C14 C 0.22091(6) 0.57692(9) 0.04463(8) 0.0288(2) Uani 1 1 d . . . C15 C 0.14354(6) 0.57678(10) -0.03138(9) 0.0341(2) Uani 1 1 d . . . C16 C 0.09997(6) 0.51358(10) -0.00340(10) 0.0365(3) Uani 1 1 d . . . C17 C 0.13351(6) 0.44835(10) 0.10000(10) 0.0337(2) Uani 1 1 d . . . C18 C 0.21128(5) 0.44528(9) 0.17537(8) 0.0285(2) Uani 1 1 d . . . H5 H 0.5829(7) 0.6827(13) 0.4337(11) 0.036(3) Uiso 1 1 d . . . H6 H 0.6729(7) 0.5171(13) 0.5359(11) 0.034(3) Uiso 1 1 d . . . H8 H 0.5027(7) 0.2489(13) 0.4139(11) 0.029(3) Uiso 1 1 d . . . H7 H 0.6321(7) 0.2971(13) 0.5263(11) 0.035(3) Uiso 1 1 d . . . H10 H 0.3601(7) 0.2428(12) 0.3378(11) 0.025(3) Uiso 1 1 d . . . H11A H 0.4066(7) 0.2036(13) 0.1859(12) 0.037(3) Uiso 1 1 d . . . H11B H 0.3950(7) 0.0841(14) 0.2526(12) 0.038(3) Uiso 1 1 d . . . H12A H 0.2654(8) 0.1519(15) 0.1613(13) 0.045(4) Uiso 1 1 d . . . H12B H 0.2806(8) 0.2685(14) 0.0953(13) 0.044(4) Uiso 1 1 d . . . H14 H 0.2519(7) 0.6217(12) 0.0252(10) 0.032(3) Uiso 1 1 d . . . H15 H 0.1200(7) 0.6205(14) -0.1051(12) 0.039(3) Uiso 1 1 d . . . H16 H 0.0454(8) 0.5159(14) -0.0549(12) 0.043(4) Uiso 1 1 d . . . H17 H 0.1036(7) 0.4035(14) 0.1220(11) 0.036(3) Uiso 1 1 d . . . H18 H 0.2355(7) 0.3993(13) 0.2498(11) 0.034(3) 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 O1 0.0290(3) 0.0205(3) 0.0271(3) 0.0020(2) 0.0155(3) 0.0002(2) O2 0.0396(4) 0.0214(3) 0.0369(4) 0.0017(3) 0.0219(3) -0.0025(3) C1 0.0256(4) 0.0211(4) 0.0184(4) 0.0001(3) 0.0129(3) -0.0010(3) C2 0.0280(4) 0.0212(4) 0.0211(4) 0.0008(3) 0.0151(3) -0.0007(3) C3 0.0305(4) 0.0235(4) 0.0232(4) 0.0001(3) 0.0174(4) -0.0011(3) C4 0.0274(4) 0.0227(4) 0.0200(4) -0.0004(3) 0.0153(3) -0.0014(3) C5 0.0302(5) 0.0271(4) 0.0241(4) -0.0022(3) 0.0172(4) -0.0054(4) C6 0.0250(4) 0.0339(5) 0.0251(4) -0.0010(3) 0.0144(4) -0.0035(4) C7 0.0267(4) 0.0303(5) 0.0262(4) 0.0016(3) 0.0155(4) 0.0020(4) C8 0.0275(4) 0.0229(4) 0.0245(4) 0.0011(3) 0.0154(4) 0.0005(3) C9 0.0255(4) 0.0215(4) 0.0189(4) -0.0002(3) 0.0141(3) -0.0002(3) C10 0.0271(4) 0.0205(4) 0.0216(4) 0.0008(3) 0.0128(3) -0.0015(3) C11 0.0411(6) 0.0235(4) 0.0321(5) -0.0028(4) 0.0224(4) -0.0010(4) C12 0.0371(5) 0.0271(5) 0.0264(5) -0.0029(4) 0.0097(4) -0.0030(4) C13 0.0275(4) 0.0229(4) 0.0229(4) -0.0004(3) 0.0135(4) 0.0029(3) C14 0.0344(5) 0.0251(4) 0.0259(4) 0.0021(3) 0.0167(4) 0.0074(4) C15 0.0358(5) 0.0284(5) 0.0265(5) -0.0008(4) 0.0109(4) 0.0117(4) C16 0.0265(5) 0.0298(5) 0.0384(5) -0.0097(4) 0.0096(4) 0.0051(4) C17 0.0293(5) 0.0285(5) 0.0422(6) -0.0075(4) 0.0196(5) -0.0019(4) C18 0.0289(5) 0.0272(5) 0.0290(4) -0.0018(4) 0.0162(4) -0.0006(4) _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 O1 C2 1.3901(11) . ? O1 C3 1.3740(11) . ? O2 C3 1.2090(12) . ? C1 C2 1.3515(12) . ? C1 C9 1.4596(12) . ? C1 C10 1.4917(12) . ? C2 C13 1.4805(12) . ? C3 C4 1.4573(13) . ? C4 C5 1.4015(13) . ? C4 C9 1.4037(12) . ? C5 C6 1.3786(14) . ? C5 H5 0.985(14) . ? C6 C7 1.3961(14) . ? C6 H6 0.983(13) . ? C7 C8 1.3867(13) . ? C7 H7 1.003(13) . ? C8 C9 1.4061(12) . ? C8 H8 0.991(13) . ? C10 C11 1.5122(14) . ? C10 C12 1.5031(13) . ? C10 H10 0.972(12) . ? C11 C12 1.4992(16) . ? C11 H11A 0.964(14) . ? C11 H11B 1.007(14) . ? C12 H12A 1.011(15) . ? C12 H12B 0.952(15) . ? C13 C14 1.4038(13) . ? C13 C18 1.3930(14) . ? C14 C15 1.3888(15) . ? C14 H14 0.978(13) . ? C15 C16 1.3835(18) . ? C15 H15 0.978(14) . ? C16 C17 1.3899(17) . ? C16 H16 0.977(14) . ? C17 C18 1.3950(14) . ? C17 H17 0.984(14) . ? C18 H18 0.995(13) . ? 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 C3 O1 C2 123.17(7) . . ? C2 C1 C9 118.29(8) . . ? C2 C1 C10 123.43(8) . . ? C9 C1 C10 118.28(8) . . ? O1 C2 C13 108.84(7) . . ? C1 C2 O1 122.01(8) . . ? C1 C2 C13 129.14(8) . . ? O1 C3 C4 116.67(8) . . ? O2 C3 O1 117.16(9) . . ? O2 C3 C4 126.17(9) . . ? C5 C4 C3 118.51(8) . . ? C5 C4 C9 121.20(8) . . ? C9 C4 C3 120.28(8) . . ? C4 C5 H5 117.8(8) . . ? C6 C5 C4 119.86(9) . . ? C6 C5 H5 122.4(8) . . ? C5 C6 C7 119.74(9) . . ? C5 C6 H6 118.5(8) . . ? C7 C6 H6 121.8(8) . . ? C6 C7 H7 120.1(7) . . ? C8 C7 C6 120.70(9) . . ? C8 C7 H7 119.2(7) . . ? C7 C8 C9 120.59(9) . . ? C7 C8 H8 119.7(7) . . ? C9 C8 H8 119.7(7) . . ? C4 C9 C1 119.54(8) . . ? C4 C9 C8 117.89(8) . . ? C8 C9 C1 122.56(8) . . ? C1 C10 C11 119.14(8) . . ? C1 C10 C12 121.84(8) . . ? C1 C10 H10 115.3(7) . . ? C11 C10 H10 115.1(7) . . ? C12 C10 C11 59.63(7) . . ? C12 C10 H10 114.5(7) . . ? C10 C11 H11A 117.0(8) . . ? C10 C11 H11B 118.6(8) . . ? C12 C11 C10 59.89(7) . . ? C12 C11 H11A 117.1(8) . . ? C12 C11 H11B 117.8(8) . . ? H11A C11 H11B 115.2(11) . . ? C10 C12 H12A 116.3(9) . . ? C10 C12 H12B 116.2(9) . . ? C11 C12 C10 60.49(7) . . ? C11 C12 H12A 117.8(8) . . ? C11 C12 H12B 116.7(9) . . ? H12A C12 H12B 117.2(12) . . ? C14 C13 C2 119.08(9) . . ? C18 C13 C2 121.90(8) . . ? C18 C13 C14 119.02(9) . . ? C13 C14 H14 119.3(7) . . ? C15 C14 C13 120.45(10) . . ? C15 C14 H14 120.2(7) . . ? C14 C15 H15 119.9(8) . . ? C16 C15 C14 120.05(10) . . ? C16 C15 H15 120.1(8) . . ? C15 C16 C17 120.13(10) . . ? C15 C16 H16 120.7(9) . . ? C17 C16 H16 119.2(9) . . ? C16 C17 C18 120.07(10) . . ? C16 C17 H17 121.5(8) . . ? C18 C17 H17 118.4(8) . . ? C13 C18 C17 120.25(9) . . ? C13 C18 H18 119.4(7) . . ? C17 C18 H18 120.3(7) . . ? #==END data_6ae_dk80 _database_code_depnum_ccdc_archive 'CCDC 901338' #TrackingRef '- OBC_026250.cif' _audit_creation_date 2012-04-02 _audit_creation_method ; Olex2 1.2-beta (compiled 2012.03.20 svn.r2253, GUI svn.r4124) ; _chemical_name_common 4-cyclopropyl-3-(3-trifluoromethylphenyl-1H-isochromen-1-one _chemical_name_systematic ; 4-cyclopropyl-3-(3-trifluoromethylphenyl-1H-isochromen-1-one ; _chemical_formula_moiety 'C19 H13 F3 O2' _chemical_formula_sum 'C19 H13 F3 O2' _chemical_formula_weight 330.29 _chemical_melting_point ? 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' F F 0.0171 0.0103 '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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 13.3582(7) _cell_length_b 14.6219(8) _cell_length_c 7.6852(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.502(2) _cell_angle_gamma 90.00 _cell_volume 1501.03(14) _cell_formula_units_Z 4 _cell_measurement_reflns_used 7488 _cell_measurement_temperature 120 _cell_measurement_theta_max 30.98 _cell_measurement_theta_min 2.79 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.6522 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2006/1 (Bruker,2006) was used for absorption correction. R(int) was 0.0455 before and 0.0249 after correction. The Ratio of minimum to maximum transmission is 0.6522. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'dull light colourless' _exptl_crystal_colour_lustre dull _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description prizm _exptl_crystal_F_000 680 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.18 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of \w scans each set at different \f and/or 2\q angles and each scan (5 s exposure) covering -0.200\% degrees in \w. The crystal to detector distance was 4.85 cm. ; _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_unetI/netI 0.0212 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 22487 _diffrn_reflns_theta_full 28.00 _diffrn_reflns_theta_max 28.00 _diffrn_reflns_theta_min 2.79 _diffrn_ambient_temperature 120 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_target Mo _diffrn_source_type 'sealed X-ray tube' _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3002 _reflns_number_total 3608 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.990 _refine_diff_density_min -1.062 _refine_diff_density_rms 0.074 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 278 _refine_ls_number_reflns 3608 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0881 _refine_ls_R_factor_gt 0.0754 _refine_ls_restrained_S_all 1.221 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+2.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1969 _refine_ls_wR_factor_ref 0.2099 _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. CF3-group is disordered over three positions, which were refined with fixed SOF 0.5:0.3:0.2 and a number of constrains of CF distances were applied. ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 F1 F -0.0837(3) 0.4517(2) 0.2372(7) 0.0452(12) Uiso 0.50 1 d PD A 1 F1A F -0.0986(4) 0.4431(3) 0.1823(9) 0.0232(11) Uiso 0.30 1 d PD A 2 F1B F -0.1176(11) 0.4138(11) 0.1185(17) 0.077(4) Uiso 0.20 1 d PD A 3 F2 F -0.1086(3) 0.3241(4) 0.3798(5) 0.0494(10) Uiso 0.50 1 d PD A 1 F2A F -0.0859(5) 0.3573(5) 0.4111(5) 0.0278(11) Uiso 0.30 1 d PD A 2 F2B F -0.0600(10) 0.3976(9) 0.3955(10) 0.062(3) Uiso 0.20 1 d PD A 3 F3 F -0.1420(3) 0.3324(3) 0.1112(6) 0.0542(11) Uiso 0.50 1 d PD A 1 F3A F -0.1490(4) 0.3042(5) 0.1822(11) 0.0492(16) Uiso 0.30 1 d PD A 2 F3B F -0.1321(7) 0.2907(5) 0.2921(15) 0.048(2) Uiso 0.20 1 d PD A 3 O1 O 0.31973(13) 0.38774(12) -0.1220(2) 0.0259(4) Uani 1 1 d . . . O2 O 0.42603(15) 0.39324(13) -0.3387(2) 0.0320(5) Uani 1 1 d . . . C1 C 0.38951(18) 0.43366(17) -0.2175(3) 0.0248(5) Uani 1 1 d . . . C2 C 0.26927(17) 0.42681(17) 0.0167(3) 0.0235(5) Uani 1 1 d . . . C3 C 0.28859(18) 0.51255(16) 0.0721(3) 0.0239(5) Uani 1 1 d . . . C4 C 0.36100(18) 0.56683(16) -0.0234(3) 0.0231(5) Uani 1 1 d . . . C5 C 0.3823(2) 0.65842(17) 0.0185(3) 0.0273(5) Uani 1 1 d . . . C6 C 0.4528(2) 0.70680(18) -0.0743(3) 0.0296(5) Uani 1 1 d . . . C7 C 0.5047(2) 0.66595(18) -0.2105(3) 0.0291(5) Uani 1 1 d . . . C8 C 0.48319(19) 0.57705(18) -0.2575(3) 0.0270(5) Uani 1 1 d . . . C9 C 0.41150(18) 0.52760(16) -0.1645(3) 0.0239(5) Uani 1 1 d . . . C10 C 0.23844(19) 0.55211(17) 0.2281(3) 0.0274(5) Uani 1 1 d . . . C11 C 0.3007(2) 0.5826(2) 0.3836(4) 0.0334(6) Uani 1 1 d . . . C12 C 0.2359(2) 0.4992(2) 0.3964(4) 0.0353(6) Uani 1 1 d . . . C13 C 0.19469(18) 0.36102(17) 0.0820(3) 0.0252(5) Uani 1 1 d . . . C14 C 0.09903(19) 0.39045(18) 0.1290(3) 0.0269(5) Uani 1 1 d . . . C15 C 0.02898(19) 0.32749(19) 0.1856(3) 0.0291(5) Uani 1 1 d . A . C16 C 0.0514(2) 0.23491(19) 0.1957(3) 0.0304(6) Uani 1 1 d . . . C17 C 0.1460(2) 0.20557(18) 0.1480(3) 0.0298(6) Uani 1 1 d . . . C18 C 0.2171(2) 0.26773(17) 0.0914(3) 0.0269(5) Uani 1 1 d . . . C19 C -0.0733(2) 0.35907(17) 0.2351(3) 0.0407(7) Uani 1 1 d D . . H5 H 0.347(2) 0.687(2) 0.120(4) 0.034(8) Uiso 1 1 d . . . H6 H 0.469(3) 0.769(3) -0.041(5) 0.044(10) Uiso 1 1 d . . . H7 H 0.556(3) 0.700(2) -0.276(4) 0.033(8) Uiso 1 1 d . . . H8 H 0.515(2) 0.548(2) -0.355(4) 0.022(7) Uiso 1 1 d . . . H10 H 0.179(2) 0.589(2) 0.201(4) 0.029(8) Uiso 1 1 d . . . H11A H 0.374(3) 0.573(2) 0.379(4) 0.032(8) Uiso 1 1 d . . . H11B H 0.280(3) 0.639(3) 0.444(5) 0.044(10) Uiso 1 1 d . . . H12A H 0.179(3) 0.503(3) 0.465(5) 0.049(10) Uiso 1 1 d . . . H12B H 0.271(3) 0.437(3) 0.394(5) 0.043(9) Uiso 1 1 d . . . H14 H 0.081(3) 0.453(3) 0.117(5) 0.039(9) Uiso 1 1 d . . . H16 H 0.002(3) 0.191(3) 0.237(5) 0.038(9) Uiso 1 1 d . . . H17 H 0.164(3) 0.140(3) 0.153(5) 0.038(9) Uiso 1 1 d . . . H18 H 0.284(2) 0.248(2) 0.064(4) 0.027(7) 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 O1 0.0271(9) 0.0246(8) 0.0262(9) -0.0026(7) 0.0052(7) -0.0004(7) O2 0.0368(10) 0.0296(9) 0.0299(9) -0.0037(7) 0.0086(8) 0.0018(8) C1 0.0243(11) 0.0265(11) 0.0236(11) 0.0013(9) 0.0021(9) 0.0031(9) C2 0.0215(11) 0.0266(11) 0.0225(11) 0.0004(9) 0.0021(8) 0.0031(9) C3 0.0226(11) 0.0249(11) 0.0242(11) 0.0008(9) 0.0015(8) 0.0025(9) C4 0.0229(11) 0.0236(11) 0.0229(11) 0.0014(9) -0.0008(8) 0.0032(8) C5 0.0305(12) 0.0251(12) 0.0264(12) 0.0004(9) 0.0010(9) 0.0016(9) C6 0.0340(13) 0.0260(12) 0.0288(12) 0.0028(10) -0.0018(10) -0.0017(10) C7 0.0285(12) 0.0309(13) 0.0278(12) 0.0066(10) -0.0004(10) -0.0027(10) C8 0.0260(12) 0.0313(13) 0.0239(11) 0.0026(9) 0.0024(9) 0.0015(9) C9 0.0235(11) 0.0253(11) 0.0228(11) 0.0021(9) 0.0000(8) 0.0022(9) C10 0.0283(12) 0.0243(11) 0.0297(12) -0.0024(9) 0.0051(9) 0.0016(9) C11 0.0382(15) 0.0328(14) 0.0293(13) -0.0066(10) 0.0055(11) -0.0016(11) C12 0.0456(16) 0.0338(14) 0.0265(13) -0.0031(10) 0.0110(11) -0.0044(12) C13 0.0249(11) 0.0274(12) 0.0232(11) 0.0002(9) -0.0002(9) -0.0003(9) C14 0.0251(12) 0.0274(12) 0.0281(12) 0.0006(9) 0.0018(9) 0.0016(9) C15 0.0275(12) 0.0342(13) 0.0255(12) 0.0000(10) 0.0014(9) -0.0004(10) C16 0.0315(13) 0.0329(13) 0.0267(12) 0.0022(10) -0.0001(10) -0.0059(10) C17 0.0348(13) 0.0268(12) 0.0278(12) -0.0002(10) -0.0010(10) -0.0026(10) C18 0.0280(12) 0.0268(12) 0.0257(12) -0.0012(9) 0.0014(9) 0.0010(9) C19 0.0293(14) 0.0443(16) 0.0487(17) 0.0074(13) 0.0083(12) 0.0003(12) _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 F1 C19 1.362(4) . ? F1A C19 1.336(4) . ? F1B C19 1.336(5) . ? F2 C19 1.315(3) . ? F2A C19 1.364(4) . ? F2B C19 1.366(5) . ? F3 C19 1.373(4) . ? F3A C19 1.351(4) . ? F3B C19 1.347(4) . ? O1 C1 1.367(3) . ? O1 C2 1.389(3) . ? O2 C1 1.210(3) . ? C1 C9 1.462(3) . ? C2 C3 1.348(3) . ? C2 C13 1.476(3) . ? C3 C4 1.455(3) . ? C3 C10 1.495(3) . ? C4 C5 1.406(3) . ? C4 C9 1.404(3) . ? C5 C6 1.381(4) . ? C5 H5 1.00(3) . ? C6 C7 1.395(4) . ? C6 H6 0.96(4) . ? C7 C8 1.379(4) . ? C7 H7 0.99(3) . ? C8 C9 1.401(3) . ? C8 H8 0.97(3) . ? C10 C11 1.517(4) . ? C10 C12 1.507(4) . ? C10 H10 0.98(3) . ? C11 C12 1.500(4) . ? C11 H11A 0.99(3) . ? C11 H11B 0.99(4) . ? C12 H12A 0.93(4) . ? C12 H12B 1.02(4) . ? C13 C14 1.399(3) . ? C13 C18 1.398(3) . ? C14 C15 1.385(4) . ? C14 H14 0.95(4) . ? C15 C16 1.388(4) . ? C15 C19 1.494(4) . ? C16 C17 1.387(4) . ? C16 H16 0.97(4) . ? C17 C18 1.388(4) . ? C17 H17 0.99(4) . ? C18 H18 0.96(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 C1 O1 C2 123.19(19) . . ? O1 C1 C9 116.6(2) . . ? O2 C1 O1 117.0(2) . . ? O2 C1 C9 126.3(2) . . ? O1 C2 C13 109.1(2) . . ? C3 C2 O1 122.2(2) . . ? C3 C2 C13 128.8(2) . . ? C2 C3 C4 118.3(2) . . ? C2 C3 C10 121.8(2) . . ? C4 C3 C10 119.9(2) . . ? C5 C4 C3 122.5(2) . . ? C9 C4 C3 119.5(2) . . ? C9 C4 C5 117.9(2) . . ? C4 C5 H5 118.8(19) . . ? C6 C5 C4 120.5(2) . . ? C6 C5 H5 120.7(19) . . ? C5 C6 C7 120.9(2) . . ? C5 C6 H6 120(2) . . ? C7 C6 H6 119(2) . . ? C6 C7 H7 120.8(19) . . ? C8 C7 C6 119.8(2) . . ? C8 C7 H7 119.4(19) . . ? C7 C8 C9 119.6(2) . . ? C7 C8 H8 121.9(18) . . ? C9 C8 H8 118.5(18) . . ? C4 C9 C1 120.1(2) . . ? C8 C9 C1 118.6(2) . . ? C8 C9 C4 121.2(2) . . ? C3 C10 C11 119.9(2) . . ? C3 C10 C12 120.2(2) . . ? C3 C10 H10 114.2(19) . . ? C11 C10 H10 116.3(19) . . ? C12 C10 C11 59.47(18) . . ? C12 C10 H10 116.1(19) . . ? C10 C11 H11A 118.0(19) . . ? C10 C11 H11B 118(2) . . ? C12 C11 C10 59.95(18) . . ? C12 C11 H11A 118(2) . . ? C12 C11 H11B 119(2) . . ? H11A C11 H11B 114(3) . . ? C10 C12 H12A 119(2) . . ? C10 C12 H12B 115(2) . . ? C11 C12 C10 60.59(18) . . ? C11 C12 H12A 118(2) . . ? C11 C12 H12B 117(2) . . ? H12A C12 H12B 116(3) . . ? C14 C13 C2 120.5(2) . . ? C18 C13 C2 120.6(2) . . ? C18 C13 C14 118.9(2) . . ? C13 C14 H14 120(2) . . ? C15 C14 C13 119.8(2) . . ? C15 C14 H14 120(2) . . ? C14 C15 C16 121.3(2) . . ? C14 C15 C19 119.7(2) . . ? C16 C15 C19 119.0(2) . . ? C15 C16 H16 121(2) . . ? C17 C16 C15 118.9(2) . . ? C17 C16 H16 120(2) . . ? C16 C17 C18 120.6(2) . . ? C16 C17 H17 120(2) . . ? C18 C17 H17 119(2) . . ? C13 C18 H18 118.9(18) . . ? C17 C18 C13 120.5(2) . . ? C17 C18 H18 120.4(18) . . ? F1 C19 F2A 89.6(4) . . ? F1 C19 F2B 65.9(6) . . ? F1 C19 F3 102.9(3) . . ? F1 C19 C15 113.8(3) . . ? F1A C19 F1 20.6(3) . . ? F1A C19 F2A 106.6(4) . . ? F1A C19 F2B 85.7(7) . . ? F1A C19 F3 83.4(4) . . ? F1A C19 F3A 105.6(5) . . ? F1A C19 F3B 129.4(5) . . ? F1A C19 C15 115.9(3) . . ? F1B C19 F1 50.8(8) . . ? F1B C19 F1A 30.2(7) . . ? F1B C19 F2A 128.2(8) . . ? F1B C19 F2B 114.3(10) . . ? F1B C19 F3 54.2(8) . . ? F1B C19 F3A 80.1(8) . . ? F1B C19 F3B 114.0(9) . . ? F1B C19 C15 114.5(7) . . ? F2 C19 F1 109.9(4) . . ? F2 C19 F1A 121.5(4) . . ? F2 C19 F1B 129.8(7) . . ? F2 C19 F2A 26.7(3) . . ? F2 C19 F2B 56.1(6) . . ? F2 C19 F3 103.5(4) . . ? F2 C19 F3A 75.5(4) . . ? F2 C19 F3B 38.9(5) . . ? F2 C19 C15 115.5(3) . . ? F2A C19 F2B 29.5(5) . . ? F2A C19 F3 126.5(4) . . ? F2A C19 C15 111.6(3) . . ? F2B C19 F3 145.5(6) . . ? F2B C19 C15 104.2(6) . . ? F3 C19 C15 110.0(3) . . ? F3A C19 F1 121.3(4) . . ? F3A C19 F2A 100.9(5) . . ? F3A C19 F2B 127.5(7) . . ? F3A C19 F3 29.4(3) . . ? F3A C19 C15 115.0(4) . . ? F3B C19 F1 132.4(5) . . ? F3B C19 F2A 65.6(5) . . ? F3B C19 F2B 94.9(8) . . ? F3B C19 F3 68.1(5) . . ? F3B C19 F3A 38.7(5) . . ? F3B C19 C15 113.0(5) . . ? #==END data_7aa_dk82 _database_code_depnum_ccdc_archive 'CCDC 901339' #TrackingRef '- OBC_026250.cif' _audit_creation_date 2012-04-03 _audit_creation_method ; Olex2 1.2-beta (compiled 2012.03.20 svn.r2253, GUI svn.r4124) ; _chemical_name_common 3-cyclopropyl-4-phenyl-1H-isochromen-1-one _chemical_name_systematic ; 3-cyclopropyl-4-phenyl-1H-isochromen-1-one ; _chemical_formula_moiety 'C18 H14 O2' _chemical_formula_sum 'C18 H14 O2' _chemical_formula_weight 262.29 _chemical_melting_point ? 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 8.5382(7) _cell_length_b 9.1292(8) _cell_length_c 35.608(3) _cell_angle_alpha 87.430(2) _cell_angle_beta 86.668(2) _cell_angle_gamma 75.652(2) _cell_volume 2683.1(4) _cell_formula_units_Z 8 _cell_measurement_reflns_used 2801 _cell_measurement_temperature 120 _cell_measurement_theta_max 24.25 _cell_measurement_theta_min 2.29 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_T_max . _exptl_absorpt_correction_T_min . _exptl_absorpt_correction_type none _exptl_absorpt_process_details . _exptl_crystal_colour 'dull light colourless' _exptl_crystal_colour_lustre dull _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1104 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 3 sets of \w scans each set at different \f and/or 2\q angles and each scan (10 s exposure) covering -0.300\% degrees in \w. The crystal to detector distance was 5.85 cm. ; _diffrn_reflns_av_R_equivalents 0.0816 _diffrn_reflns_av_unetI/netI 0.1484 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_number 23605 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 1.15 _diffrn_ambient_temperature 120 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 6000 area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed X-ray tube' _diffrn_source_current 40.0 _diffrn_source_power 2.0 _diffrn_source_target Mo _diffrn_source_type 'sealed X-ray tube' _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 4785 _reflns_number_total 11558 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.807 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.052 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.931 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 721 _refine_ls_number_reflns 11558 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1498 _refine_ls_R_factor_gt 0.0591 _refine_ls_restrained_S_all 0.931 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0200P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0987 _refine_ls_wR_factor_ref 0.1136 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 O1 O 0.3831(2) 0.9459(2) 0.15622(5) 0.0418(6) Uani 1 1 d . . . O2 O 0.3926(2) 0.9348(2) 0.21808(5) 0.0361(5) Uani 1 1 d . . . C1 C 0.4648(4) 0.9474(3) 0.18286(8) 0.0343(8) Uani 1 1 d . . . C2 C 0.4734(4) 0.9264(3) 0.25091(8) 0.0344(8) Uani 1 1 d . . . C3 C 0.6293(3) 0.9333(3) 0.25076(7) 0.0290(7) Uani 1 1 d . . . C4 C 0.8734(3) 0.9698(3) 0.21255(8) 0.0302(7) Uani 1 1 d . . . H4 H 0.9305 0.9649 0.2342 0.036 Uiso 1 1 calc R . . C5 C 0.9452(3) 0.9920(3) 0.17791(8) 0.0336(8) Uani 1 1 d . . . H5 H 1.0513 1.0017 0.1765 0.040 Uiso 1 1 calc R . . C6 C 0.8637(3) 1.0004(3) 0.14509(8) 0.0334(8) Uani 1 1 d . . . H6 H 0.9142 1.0162 0.1219 0.040 Uiso 1 1 calc R . . C7 C 0.7062(3) 0.9851(3) 0.14712(8) 0.0320(7) Uani 1 1 d . . . H7 H 0.6501 0.9903 0.1253 0.038 Uiso 1 1 calc R . . C8 C 0.6320(3) 0.9618(3) 0.18190(7) 0.0270(7) Uani 1 1 d . . . C9 C 0.7131(3) 0.9544(3) 0.21506(7) 0.0271(7) Uani 1 1 d . . . C10 C 0.3698(3) 0.9068(3) 0.28387(8) 0.0414(9) Uani 1 1 d . . . H10 H 0.4216 0.8981 0.3080 0.050 Uiso 1 1 calc R . . C11 C 0.2454(3) 0.8166(4) 0.28185(9) 0.0487(9) Uani 1 1 d . . . H11G H 0.2343 0.7753 0.2578 0.058 Uiso 1 1 calc R . . H11H H 0.2289 0.7533 0.3036 0.058 Uiso 1 1 calc R . . C12 C 0.1904(3) 0.9815(4) 0.28548(9) 0.0460(9) Uani 1 1 d . . . H12G H 0.1405 1.0192 0.3095 0.055 Uiso 1 1 calc R . . H12H H 0.1459 1.0413 0.2636 0.055 Uiso 1 1 calc R . . C13 C 0.7138(3) 0.9205(3) 0.28689(8) 0.0315(7) Uani 1 1 d . . . C14 C 0.8221(3) 0.7847(3) 0.29756(8) 0.0347(8) Uani 1 1 d . . . H14 H 0.8435 0.7030 0.2817 0.042 Uiso 1 1 calc R . . C15 C 0.8970(4) 0.7711(4) 0.33111(8) 0.0399(8) Uani 1 1 d . . . H15 H 0.9667 0.6796 0.3380 0.048 Uiso 1 1 calc R . . C16 C 0.8701(4) 0.8911(4) 0.35446(8) 0.0442(9) Uani 1 1 d . . . H16 H 0.9230 0.8822 0.3769 0.053 Uiso 1 1 calc R . . C17 C 0.7644(4) 1.0241(4) 0.34445(8) 0.0495(9) Uani 1 1 d . . . H17 H 0.7437 1.1051 0.3605 0.059 Uiso 1 1 calc R . . C18 C 0.6879(4) 1.0397(3) 0.31087(8) 0.0437(9) Uani 1 1 d . . . H18 H 0.6182 1.1317 0.3043 0.052 Uiso 1 1 calc R . . O1A O -0.1934(2) 0.7458(2) 0.55991(5) 0.0480(6) Uani 1 1 d . . . O2A O 0.0309(3) 0.7877(2) 0.53366(5) 0.0466(6) Uani 1 1 d . . . C1A C -0.1072(4) 0.7376(3) 0.53155(9) 0.0431(9) Uani 1 1 d . . . C2A C 0.1418(4) 0.7867(3) 0.50334(8) 0.0412(8) Uani 1 1 d . . . C3A C 0.1191(4) 0.7385(3) 0.46959(8) 0.0358(8) Uani 1 1 d . . . C4A C -0.0570(4) 0.6255(3) 0.43096(8) 0.0408(8) Uani 1 1 d . . . H4A H 0.0137 0.6239 0.4100 0.049 Uiso 1 1 calc R . . C5A C -0.1946(4) 0.5741(4) 0.42825(9) 0.0485(9) Uani 1 1 d . . . H5A H -0.2154 0.5374 0.4056 0.058 Uiso 1 1 calc R . . C6A C -0.3025(4) 0.5766(4) 0.45912(9) 0.0500(9) Uani 1 1 d . . . H6A H -0.3951 0.5416 0.4571 0.060 Uiso 1 1 calc R . . C7A C -0.2729(4) 0.6299(4) 0.49222(9) 0.0468(9) Uani 1 1 d . . . H7A H -0.3458 0.6319 0.5127 0.056 Uiso 1 1 calc R . . C8A C -0.1331(4) 0.6822(3) 0.49584(8) 0.0369(8) Uani 1 1 d . . . C9A C -0.0226(4) 0.6803(3) 0.46492(8) 0.0375(8) Uani 1 1 d . . . C10A C 0.2812(4) 0.8369(4) 0.51484(9) 0.0520(10) Uani 1 1 d . . . H10A H 0.3665 0.8353 0.4951 0.062 Uiso 1 1 calc R . . C11A C 0.3421(5) 0.8041(5) 0.55554(10) 0.0874(14) Uani 1 1 d . . . H11E H 0.2814 0.7531 0.5733 0.105 Uiso 1 1 calc R . . H11F H 0.4581 0.7779 0.5585 0.105 Uiso 1 1 calc R . . C12A C 0.2688(5) 0.9533(4) 0.54417(9) 0.0700(12) Uani 1 1 d . . . H12E H 0.3381 1.0229 0.5403 0.084 Uiso 1 1 calc R . . H12F H 0.1619 0.9981 0.5551 0.084 Uiso 1 1 calc R . . C13A C 0.2360(4) 0.7416(4) 0.43689(8) 0.0385(8) Uani 1 1 d . . . C14A C 0.3151(3) 0.6106(4) 0.41867(8) 0.0393(8) Uani 1 1 d . . . H14A H 0.2928 0.5190 0.4265 0.047 Uiso 1 1 calc R . . C15A C 0.4261(4) 0.6139(4) 0.38915(8) 0.0457(9) Uani 1 1 d . . . H15A H 0.4776 0.5251 0.3772 0.055 Uiso 1 1 calc R . . C16A C 0.4610(4) 0.7486(5) 0.37737(9) 0.0563(10) Uani 1 1 d . . . H16A H 0.5380 0.7503 0.3579 0.068 Uiso 1 1 calc R . . C17A C 0.3813(4) 0.8815(4) 0.39454(9) 0.0634(11) Uani 1 1 d . . . H17A H 0.4036 0.9728 0.3864 0.076 Uiso 1 1 calc R . . C18A C 0.2683(4) 0.8780(4) 0.42389(9) 0.0544(10) Uani 1 1 d . . . H18A H 0.2133 0.9676 0.4350 0.065 Uiso 1 1 calc R . . O1B O 0.2651(2) 0.6189(2) 0.65697(5) 0.0405(6) Uani 1 1 d . . . O2B O 0.2420(2) 0.5921(2) 0.71864(5) 0.0343(5) Uani 1 1 d . . . C1B C 0.1745(3) 0.6138(3) 0.68413(8) 0.0321(7) Uani 1 1 d . . . C2B C 0.1543(3) 0.5758(3) 0.75204(8) 0.0309(7) Uani 1 1 d . . . C3B C -0.0046(3) 0.5804(3) 0.75223(7) 0.0252(7) Uani 1 1 d . . . C4B C -0.2511(3) 0.6095(3) 0.71518(8) 0.0324(7) Uani 1 1 d . . . H4B H -0.3116 0.5939 0.7369 0.039 Uiso 1 1 calc R . . C5B C -0.3233(3) 0.6352(3) 0.68157(8) 0.0369(8) Uani 1 1 d . . . H5B H -0.4315 0.6340 0.6806 0.044 Uiso 1 1 calc R . . C6B C -0.2375(4) 0.6633(3) 0.64862(8) 0.0390(8) Uani 1 1 d . . . H6B H -0.2894 0.6848 0.6260 0.047 Uiso 1 1 calc R . . C7B C -0.0758(4) 0.6590(3) 0.64973(8) 0.0360(8) Uani 1 1 d . . . H7B H -0.0176 0.6768 0.6278 0.043 Uiso 1 1 calc R . . C8B C 0.0008(3) 0.6279(3) 0.68371(8) 0.0290(7) Uani 1 1 d . . . C9B C -0.0865(3) 0.6063(3) 0.71746(7) 0.0276(7) Uani 1 1 d . . . C10B C 0.2577(3) 0.5499(3) 0.78408(8) 0.0353(8) Uani 1 1 d . . . H10B H 0.2030 0.5330 0.8083 0.042 Uiso 1 1 calc R . . C11B C 0.3901(3) 0.6318(3) 0.78647(9) 0.0399(8) Uani 1 1 d . . . H11C H 0.4074 0.6982 0.7654 0.048 Uiso 1 1 calc R . . H11D H 0.4083 0.6654 0.8109 0.048 Uiso 1 1 calc R . . C12B C 0.4333(3) 0.4667(3) 0.78038(9) 0.0433(9) Uani 1 1 d . . . H12C H 0.4779 0.3999 0.8011 0.052 Uiso 1 1 calc R . . H12D H 0.4770 0.4326 0.7556 0.052 Uiso 1 1 calc R . . C13B C -0.0951(3) 0.5617(3) 0.78868(7) 0.0270(7) Uani 1 1 d . . . C14B C -0.1724(3) 0.6868(3) 0.80932(7) 0.0340(8) Uani 1 1 d . . . H14B H -0.1646 0.7826 0.8008 0.041 Uiso 1 1 calc R . . C15B C -0.2613(3) 0.6708(4) 0.84250(8) 0.0383(8) Uani 1 1 d . . . H15B H -0.3101 0.7552 0.8564 0.046 Uiso 1 1 calc R . . C16B C -0.2769(3) 0.5293(4) 0.85473(8) 0.0376(8) Uani 1 1 d . . . H16B H -0.3378 0.5190 0.8767 0.045 Uiso 1 1 calc R . . C17B C -0.2030(3) 0.4032(4) 0.83464(8) 0.0415(8) Uani 1 1 d . . . H17B H -0.2137 0.3080 0.8429 0.050 Uiso 1 1 calc R . . C18B C -0.1122(3) 0.4203(3) 0.80177(8) 0.0358(8) Uani 1 1 d . . . H18B H -0.0617 0.3352 0.7882 0.043 Uiso 1 1 calc R . . O1C O 0.7129(2) 0.0318(2) 1.05547(5) 0.0325(5) Uani 1 1 d . . . O2C O 0.6986(2) 0.1580(2) 1.00088(5) 0.0285(5) Uani 1 1 d . . . C1C C 0.6256(4) 0.1034(3) 1.03184(8) 0.0281(7) Uani 1 1 d . . . C2C C 0.6126(3) 0.2447(3) 0.97222(7) 0.0254(7) Uani 1 1 d . . . C3C C 0.4496(3) 0.2832(3) 0.97314(7) 0.0226(6) Uani 1 1 d . . . C4C C 0.1925(3) 0.2641(3) 1.00826(8) 0.0307(7) Uani 1 1 d . . . H4C H 0.1322 0.3226 0.9896 0.037 Uiso 1 1 calc R . . C5C C 0.1149(3) 0.2120(3) 1.03906(8) 0.0362(8) Uani 1 1 d . . . H5C H 0.0024 0.2351 1.0408 0.043 Uiso 1 1 calc R . . C6C C 0.2012(4) 0.1262(3) 1.06736(8) 0.0390(8) Uani 1 1 d . . . H6C H 0.1469 0.0932 1.0882 0.047 Uiso 1 1 calc R . . C7C C 0.3685(3) 0.0891(3) 1.06480(7) 0.0325(7) Uani 1 1 d . . . H7C H 0.4271 0.0301 1.0837 0.039 Uiso 1 1 calc R . . C8C C 0.4490(3) 0.1413(3) 1.03354(7) 0.0244(7) Uani 1 1 d . . . C9C C 0.3625(3) 0.2293(3) 1.00493(7) 0.0241(7) Uani 1 1 d . . . C10C C 0.7215(3) 0.2878(3) 0.94290(7) 0.0299(7) Uani 1 1 d . . . H10C H 0.6748 0.3143 0.9183 0.036 Uiso 1 1 calc R . . C11C C 0.9011(3) 0.2202(3) 0.94169(8) 0.0354(8) Uani 1 1 d . . . H11A H 0.9435 0.1448 0.9610 0.042 Uiso 1 1 calc R . . H11B H 0.9568 0.2032 0.9171 0.042 Uiso 1 1 calc R . . C12C C 0.8384(3) 0.3797(3) 0.95331(8) 0.0364(8) Uani 1 1 d . . . H12A H 0.8554 0.4593 0.9358 0.044 Uiso 1 1 calc R . . H12B H 0.8421 0.4007 0.9797 0.044 Uiso 1 1 calc R . . C13C C 0.3643(3) 0.3828(3) 0.94275(7) 0.0249(7) Uani 1 1 d . . . C14C C 0.2682(3) 0.3328(3) 0.91830(7) 0.0336(8) Uani 1 1 d . . . H14C H 0.2579 0.2337 0.9206 0.040 Uiso 1 1 calc R . . C15C C 0.1878(3) 0.4296(3) 0.89067(8) 0.0357(8) Uani 1 1 d . . . H15C H 0.1243 0.3946 0.8745 0.043 Uiso 1 1 calc R . . C16C C 0.2008(3) 0.5764(3) 0.88679(8) 0.0346(8) Uani 1 1 d . . . H16C H 0.1455 0.6408 0.8683 0.041 Uiso 1 1 calc R . . C17C C 0.2959(3) 0.6278(3) 0.91035(7) 0.0347(8) Uani 1 1 d . . . H17C H 0.3069 0.7265 0.9076 0.042 Uiso 1 1 calc R . . C18C C 0.3760(3) 0.5315(3) 0.93844(7) 0.0296(7) Uani 1 1 d . . . H18C H 0.4385 0.5677 0.9546 0.036 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 O1 0.0428(13) 0.0522(16) 0.0324(12) 0.0018(11) -0.0091(11) -0.0143(12) O2 0.0319(12) 0.0477(14) 0.0287(11) 0.0030(10) -0.0003(10) -0.0110(11) C1 0.043(2) 0.0284(19) 0.0312(18) -0.0014(15) 0.0008(16) -0.0078(16) C2 0.0378(19) 0.036(2) 0.0282(17) 0.0016(15) -0.0017(15) -0.0063(16) C3 0.0293(18) 0.0298(19) 0.0262(16) 0.0000(14) -0.0013(14) -0.0043(15) C4 0.0286(17) 0.0301(19) 0.0318(17) 0.0001(14) -0.0016(14) -0.0068(15) C5 0.0288(17) 0.033(2) 0.0377(18) -0.0010(15) 0.0029(15) -0.0062(15) C6 0.043(2) 0.0301(19) 0.0255(16) 0.0015(14) 0.0061(15) -0.0074(16) C7 0.0338(18) 0.0314(19) 0.0297(17) -0.0015(14) -0.0021(15) -0.0058(16) C8 0.0294(17) 0.0246(18) 0.0255(16) -0.0005(13) 0.0009(14) -0.0041(14) C9 0.0287(17) 0.0196(17) 0.0304(16) -0.0028(13) 0.0019(14) -0.0013(14) C10 0.0345(19) 0.061(2) 0.0293(17) 0.0047(16) 0.0016(15) -0.0138(18) C11 0.042(2) 0.047(2) 0.056(2) 0.0041(18) 0.0102(18) -0.0123(19) C12 0.040(2) 0.048(2) 0.046(2) -0.0020(17) 0.0057(17) -0.0064(18) C13 0.0341(18) 0.033(2) 0.0265(16) -0.0015(14) 0.0005(14) -0.0077(16) C14 0.0417(19) 0.030(2) 0.0286(16) -0.0039(14) -0.0019(15) -0.0009(16) C15 0.049(2) 0.036(2) 0.0324(17) 0.0045(16) -0.0099(16) -0.0049(17) C16 0.059(2) 0.047(2) 0.0293(17) 0.0022(17) -0.0103(17) -0.018(2) C17 0.080(3) 0.034(2) 0.0323(18) -0.0083(16) -0.0110(19) -0.007(2) C18 0.065(2) 0.027(2) 0.0332(18) -0.0004(15) -0.0092(17) 0.0014(18) O1A 0.0566(15) 0.0490(15) 0.0342(12) -0.0036(11) 0.0136(12) -0.0080(12) O2A 0.0564(15) 0.0501(15) 0.0320(12) -0.0092(11) 0.0110(11) -0.0124(13) C1A 0.051(2) 0.036(2) 0.037(2) 0.0023(16) 0.0039(18) -0.0027(18) C2A 0.049(2) 0.039(2) 0.0333(18) -0.0063(16) 0.0084(17) -0.0068(18) C3A 0.044(2) 0.0302(19) 0.0284(17) 0.0019(14) 0.0038(15) -0.0019(16) C4A 0.039(2) 0.045(2) 0.0322(18) 0.0034(16) -0.0007(16) -0.0002(17) C5A 0.048(2) 0.057(2) 0.0339(19) -0.0004(17) -0.0024(17) -0.0007(19) C6A 0.041(2) 0.065(3) 0.041(2) 0.0059(19) -0.0066(18) -0.0078(19) C7A 0.045(2) 0.050(2) 0.039(2) 0.0046(17) 0.0029(18) -0.0004(18) C8A 0.044(2) 0.034(2) 0.0264(17) 0.0025(14) 0.0035(15) 0.0002(17) C9A 0.046(2) 0.030(2) 0.0278(17) 0.0036(14) 0.0015(16) 0.0046(16) C10A 0.061(2) 0.057(3) 0.042(2) -0.0138(18) 0.0133(19) -0.024(2) C11A 0.096(3) 0.110(4) 0.057(3) -0.018(3) 0.006(3) -0.025(3) C12A 0.092(3) 0.046(3) 0.050(2) 0.012(2) 0.001(2) 0.022(2) C13A 0.044(2) 0.036(2) 0.0304(17) 0.0008(15) 0.0047(16) -0.0015(17) C14A 0.042(2) 0.042(2) 0.0314(17) -0.0016(15) 0.0016(16) -0.0061(17) C15A 0.044(2) 0.063(3) 0.0247(17) -0.0075(17) 0.0022(16) -0.0020(19) C16A 0.051(2) 0.082(3) 0.0291(19) 0.008(2) 0.0077(17) -0.009(2) C17A 0.077(3) 0.058(3) 0.050(2) 0.015(2) 0.018(2) -0.014(2) C18A 0.067(3) 0.044(2) 0.045(2) 0.0029(18) 0.0188(19) -0.005(2) O1B 0.0393(13) 0.0472(14) 0.0334(12) -0.0051(10) 0.0156(11) -0.0108(11) O2B 0.0299(12) 0.0443(14) 0.0286(11) -0.0036(10) 0.0060(10) -0.0102(10) C1B 0.0382(19) 0.0282(19) 0.0297(17) -0.0037(14) 0.0034(16) -0.0083(16) C2B 0.0313(18) 0.0320(19) 0.0275(16) -0.0051(14) 0.0045(15) -0.0047(15) C3B 0.0249(16) 0.0251(17) 0.0243(15) -0.0041(13) 0.0012(13) -0.0035(14) C4B 0.0278(17) 0.038(2) 0.0287(17) -0.0048(14) 0.0000(14) -0.0035(16) C5B 0.0308(18) 0.044(2) 0.0345(18) -0.0073(16) -0.0013(15) -0.0051(16) C6B 0.043(2) 0.044(2) 0.0257(16) -0.0060(15) -0.0030(15) 0.0006(17) C7B 0.038(2) 0.038(2) 0.0300(17) -0.0073(15) 0.0120(15) -0.0079(17) C8B 0.0316(18) 0.0262(18) 0.0274(16) -0.0061(14) 0.0020(14) -0.0034(15) C9B 0.0281(17) 0.0234(17) 0.0278(16) -0.0050(13) 0.0020(14) 0.0003(14) C10B 0.0298(18) 0.044(2) 0.0327(17) -0.0002(15) -0.0003(15) -0.0103(17) C11B 0.0313(18) 0.044(2) 0.0447(19) -0.0059(16) -0.0025(15) -0.0099(17) C12B 0.0345(19) 0.042(2) 0.050(2) 0.0007(17) -0.0017(16) -0.0043(17) C13B 0.0249(16) 0.0317(19) 0.0245(15) -0.0024(14) 0.0023(13) -0.0080(15) C14B 0.0399(19) 0.035(2) 0.0270(16) 0.0000(14) -0.0003(15) -0.0091(16) C15B 0.0377(19) 0.043(2) 0.0292(17) -0.0094(15) 0.0068(15) -0.0013(17) C16B 0.0341(19) 0.048(2) 0.0260(16) 0.0082(16) 0.0043(14) -0.0036(17) C17B 0.044(2) 0.041(2) 0.0370(19) 0.0117(16) 0.0019(16) -0.0087(17) C18B 0.0394(19) 0.030(2) 0.0352(18) -0.0023(15) 0.0008(15) -0.0044(16) O1C 0.0372(12) 0.0344(13) 0.0255(10) 0.0021(9) -0.0063(10) -0.0077(11) O2C 0.0284(11) 0.0334(13) 0.0235(10) 0.0014(9) -0.0012(9) -0.0077(10) C1C 0.0365(19) 0.0253(19) 0.0249(16) -0.0050(14) -0.0045(15) -0.0110(16) C2C 0.0323(18) 0.0227(18) 0.0208(15) 0.0018(13) -0.0046(14) -0.0058(15) C3C 0.0252(16) 0.0212(17) 0.0205(14) -0.0010(12) -0.0031(13) -0.0034(14) C4C 0.0297(17) 0.0340(19) 0.0276(16) -0.0024(14) -0.0016(14) -0.0061(15) C5C 0.0245(17) 0.050(2) 0.0359(18) -0.0068(16) 0.0031(15) -0.0120(16) C6C 0.042(2) 0.054(2) 0.0268(17) -0.0046(16) 0.0076(16) -0.0230(18) C7C 0.042(2) 0.033(2) 0.0245(16) -0.0002(14) -0.0038(15) -0.0127(16) C8C 0.0284(17) 0.0254(18) 0.0213(15) -0.0030(13) 0.0014(13) -0.0105(14) C9C 0.0265(16) 0.0240(17) 0.0229(15) -0.0085(13) -0.0010(13) -0.0068(14) C10C 0.0292(17) 0.0361(19) 0.0250(15) 0.0028(14) 0.0029(14) -0.0110(15) C11C 0.0314(18) 0.040(2) 0.0346(17) -0.0023(15) 0.0045(15) -0.0104(16) C12C 0.0356(18) 0.038(2) 0.0394(18) -0.0018(15) 0.0030(15) -0.0164(16) C13C 0.0219(16) 0.0271(18) 0.0244(15) -0.0020(13) -0.0005(13) -0.0035(14) C14C 0.0357(18) 0.035(2) 0.0319(17) 0.0039(15) -0.0060(15) -0.0121(16) C15C 0.0349(19) 0.043(2) 0.0309(17) 0.0015(15) -0.0089(15) -0.0118(17) C16C 0.0380(19) 0.033(2) 0.0277(16) -0.0001(14) -0.0016(15) -0.0001(16) C17C 0.041(2) 0.031(2) 0.0315(17) -0.0008(15) -0.0018(15) -0.0075(16) C18C 0.0299(17) 0.032(2) 0.0263(16) -0.0008(14) -0.0035(14) -0.0067(15) _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 O1 C1 1.212(3) . ? O2 C1 1.378(3) . ? O2 C2 1.381(3) . ? C1 C8 1.465(4) . ? C2 C3 1.348(3) . ? C2 C10 1.459(3) . ? C3 C9 1.451(3) . ? C3 C13 1.498(4) . ? C4 H4 0.9300 . ? C4 C5 1.375(3) . ? C4 C9 1.407(3) . ? C5 H5 0.9300 . ? C5 C6 1.384(4) . ? C6 H6 0.9300 . ? C6 C7 1.383(3) . ? C7 H7 0.9300 . ? C7 C8 1.390(3) . ? C8 C9 1.394(4) . ? C10 H10 0.9800 . ? C10 C11 1.503(4) . ? C10 C12 1.513(4) . ? C11 H11G 0.9700 . ? C11 H11H 0.9700 . ? C11 C12 1.471(4) . ? C12 H12G 0.9700 . ? C12 H12H 0.9700 . ? C13 C14 1.402(4) . ? C13 C18 1.380(4) . ? C14 H14 0.9300 . ? C14 C15 1.374(4) . ? C15 H15 0.9300 . ? C15 C16 1.371(4) . ? C16 H16 0.9300 . ? C16 C17 1.368(4) . ? C17 H17 0.9300 . ? C17 C18 1.380(4) . ? C18 H18 0.9300 . ? O1A C1A 1.209(3) . ? O2A C1A 1.373(3) . ? O2A C2A 1.393(3) . ? C1A C8A 1.438(4) . ? C2A C3A 1.339(4) . ? C2A C10A 1.463(4) . ? C3A C9A 1.456(4) . ? C3A C13A 1.493(4) . ? C4A H4A 0.9300 . ? C4A C5A 1.379(4) . ? C4A C9A 1.403(4) . ? C5A H5A 0.9300 . ? C5A C6A 1.390(4) . ? C6A H6A 0.9300 . ? C6A C7A 1.356(4) . ? C7A H7A 0.9300 . ? C7A C8A 1.405(4) . ? C8A C9A 1.406(3) . ? C10A H10A 0.9800 . ? C10A C11A 1.559(5) . ? C10A C12A 1.504(4) . ? C11A H11E 0.9700 . ? C11A H11F 0.9700 . ? C11A C12A 1.403(5) . ? C12A H12E 0.9700 . ? C12A H12F 0.9700 . ? C13A C14A 1.388(4) . ? C13A C18A 1.394(4) . ? C14A H14A 0.9300 . ? C14A C15A 1.379(3) . ? C15A H15A 0.9300 . ? C15A C16A 1.378(4) . ? C16A H16A 0.9300 . ? C16A C17A 1.385(4) . ? C17A H17A 0.9300 . ? C17A C18A 1.386(4) . ? C18A H18A 0.9300 . ? O1B C1B 1.209(3) . ? O2B C1B 1.373(3) . ? O2B C2B 1.390(3) . ? C1B C8B 1.458(4) . ? C2B C3B 1.347(3) . ? C2B C10B 1.458(4) . ? C3B C9B 1.439(4) . ? C3B C13B 1.496(3) . ? C4B H4B 0.9300 . ? C4B C5B 1.362(4) . ? C4B C9B 1.406(4) . ? C5B H5B 0.9300 . ? C5B C6B 1.394(3) . ? C6B H6B 0.9300 . ? C6B C7B 1.374(4) . ? C7B H7B 0.9300 . ? C7B C8B 1.393(4) . ? C8B C9B 1.409(3) . ? C10B H10B 0.9800 . ? C10B C11B 1.510(4) . ? C10B C12B 1.505(4) . ? C11B H11C 0.9700 . ? C11B H11D 0.9700 . ? C11B C12B 1.483(4) . ? C12B H12C 0.9700 . ? C12B H12D 0.9700 . ? C13B C14B 1.387(4) . ? C13B C18B 1.392(3) . ? C14B H14B 0.9300 . ? C14B C15B 1.388(3) . ? C15B H15B 0.9300 . ? C15B C16B 1.380(4) . ? C16B H16B 0.9300 . ? C16B C17B 1.377(4) . ? C17B H17B 0.9300 . ? C17B C18B 1.390(3) . ? C18B H18B 0.9300 . ? O1C C1C 1.214(3) . ? O2C C1C 1.370(3) . ? O2C C2C 1.390(3) . ? C1C C8C 1.459(4) . ? C2C C3C 1.347(3) . ? C2C C10C 1.463(3) . ? C3C C9C 1.453(3) . ? C3C C13C 1.484(3) . ? C4C H4C 0.9300 . ? C4C C5C 1.376(3) . ? C4C C9C 1.407(3) . ? C5C H5C 0.9300 . ? C5C C6C 1.379(4) . ? C6C H6C 0.9300 . ? C6C C7C 1.382(4) . ? C7C H7C 0.9300 . ? C7C C8C 1.401(3) . ? C8C C9C 1.396(4) . ? C10C H10C 0.9800 . ? C10C C11C 1.503(3) . ? C10C C12C 1.524(3) . ? C11C H11A 0.9700 . ? C11C H11B 0.9700 . ? C11C C12C 1.490(4) . ? C12C H12A 0.9700 . ? C12C H12B 0.9700 . ? C13C C14C 1.394(3) . ? C13C C18C 1.387(3) . ? C14C H14C 0.9300 . ? C14C C15C 1.386(4) . ? C15C H15C 0.9300 . ? C15C C16C 1.373(4) . ? C16C H16C 0.9300 . ? C16C C17C 1.373(4) . ? C17C H17C 0.9300 . ? C17C C18C 1.394(4) . ? C18C H18C 0.9300 . ? 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 C1 O2 C2 123.1(2) . . ? O1 C1 O2 116.6(3) . . ? O1 C1 C8 127.3(3) . . ? O2 C1 C8 116.0(3) . . ? O2 C2 C10 111.4(2) . . ? C3 C2 O2 122.0(2) . . ? C3 C2 C10 126.6(3) . . ? C2 C3 C9 118.9(3) . . ? C2 C3 C13 120.4(2) . . ? C9 C3 C13 120.7(2) . . ? C5 C4 H4 120.2 . . ? C5 C4 C9 119.7(3) . . ? C9 C4 H4 120.2 . . ? C4 C5 H5 119.1 . . ? C4 C5 C6 121.7(3) . . ? C6 C5 H5 119.1 . . ? C5 C6 H6 120.4 . . ? C7 C6 C5 119.2(3) . . ? C7 C6 H6 120.4 . . ? C6 C7 H7 120.1 . . ? C6 C7 C8 119.8(3) . . ? C8 C7 H7 120.1 . . ? C7 C8 C1 118.1(3) . . ? C7 C8 C9 121.2(3) . . ? C9 C8 C1 120.7(2) . . ? C4 C9 C3 122.5(3) . . ? C8 C9 C3 119.2(2) . . ? C8 C9 C4 118.4(2) . . ? C2 C10 H10 115.0 . . ? C2 C10 C11 120.7(3) . . ? C2 C10 C12 121.3(3) . . ? C11 C10 H10 115.0 . . ? C11 C10 C12 58.36(18) . . ? C12 C10 H10 115.0 . . ? C10 C11 H11G 117.7 . . ? C10 C11 H11H 117.7 . . ? H11G C11 H11H 114.8 . . ? C12 C11 C10 61.16(19) . . ? C12 C11 H11G 117.7 . . ? C12 C11 H11H 117.7 . . ? C10 C12 H12G 117.7 . . ? C10 C12 H12H 117.7 . . ? C11 C12 C10 60.48(19) . . ? C11 C12 H12G 117.7 . . ? C11 C12 H12H 117.7 . . ? H12G C12 H12H 114.8 . . ? C14 C13 C3 120.4(3) . . ? C18 C13 C3 121.9(3) . . ? C18 C13 C14 117.7(3) . . ? C13 C14 H14 119.6 . . ? C15 C14 C13 120.7(3) . . ? C15 C14 H14 119.6 . . ? C14 C15 H15 119.7 . . ? C16 C15 C14 120.6(3) . . ? C16 C15 H15 119.7 . . ? C15 C16 H16 120.4 . . ? C17 C16 C15 119.2(3) . . ? C17 C16 H16 120.4 . . ? C16 C17 H17 119.6 . . ? C16 C17 C18 120.9(3) . . ? C18 C17 H17 119.6 . . ? C13 C18 H18 119.6 . . ? C17 C18 C13 120.8(3) . . ? C17 C18 H18 119.6 . . ? C1A O2A C2A 123.1(3) . . ? O1A C1A O2A 116.2(3) . . ? O1A C1A C8A 127.5(3) . . ? O2A C1A C8A 116.4(3) . . ? O2A C2A C10A 110.4(3) . . ? C3A C2A O2A 121.8(3) . . ? C3A C2A C10A 127.7(3) . . ? C2A C3A C9A 118.9(3) . . ? C2A C3A C13A 121.6(3) . . ? C9A C3A C13A 119.5(3) . . ? C5A C4A H4A 119.6 . . ? C5A C4A C9A 120.8(3) . . ? C9A C4A H4A 119.6 . . ? C4A C5A H5A 119.8 . . ? C4A C5A C6A 120.5(3) . . ? C6A C5A H5A 119.8 . . ? C5A C6A H6A 120.0 . . ? C7A C6A C5A 120.0(3) . . ? C7A C6A H6A 120.0 . . ? C6A C7A H7A 119.6 . . ? C6A C7A C8A 120.7(3) . . ? C8A C7A H7A 119.6 . . ? C7A C8A C1A 118.5(3) . . ? C7A C8A C9A 120.1(3) . . ? C9A C8A C1A 121.4(3) . . ? C4A C9A C3A 123.6(3) . . ? C4A C9A C8A 117.9(3) . . ? C8A C9A C3A 118.4(3) . . ? C2A C10A H10A 114.9 . . ? C2A C10A C11A 121.2(3) . . ? C2A C10A C12A 123.1(3) . . ? C11A C10A H10A 114.9 . . ? C12A C10A H10A 114.9 . . ? C12A C10A C11A 54.5(2) . . ? C10A C11A H11E 117.7 . . ? C10A C11A H11F 117.7 . . ? H11E C11A H11F 114.8 . . ? C12A C11A C10A 60.7(3) . . ? C12A C11A H11E 117.7 . . ? C12A C11A H11F 117.7 . . ? C10A C12A H12E 117.3 . . ? C10A C12A H12F 117.3 . . ? C11A C12A C10A 64.8(2) . . ? C11A C12A H12E 117.3 . . ? C11A C12A H12F 117.3 . . ? H12E C12A H12F 114.3 . . ? C14A C13A C3A 121.5(3) . . ? C14A C13A C18A 118.3(3) . . ? C18A C13A C3A 120.3(3) . . ? C13A C14A H14A 119.5 . . ? C15A C14A C13A 121.1(3) . . ? C15A C14A H14A 119.5 . . ? C14A C15A H15A 120.0 . . ? C16A C15A C14A 120.1(3) . . ? C16A C15A H15A 120.0 . . ? C15A C16A H16A 120.0 . . ? C15A C16A C17A 120.0(3) . . ? C17A C16A H16A 120.0 . . ? C16A C17A H17A 120.1 . . ? C16A C17A C18A 119.7(3) . . ? C18A C17A H17A 120.1 . . ? C13A C18A H18A 119.6 . . ? C17A C18A C13A 120.8(3) . . ? C17A C18A H18A 119.6 . . ? C1B O2B C2B 123.1(2) . . ? O1B C1B O2B 116.8(3) . . ? O1B C1B C8B 126.2(3) . . ? O2B C1B C8B 116.9(2) . . ? O2B C2B C10B 111.3(2) . . ? C3B C2B O2B 121.1(3) . . ? C3B C2B C10B 127.6(3) . . ? C2B C3B C9B 119.6(2) . . ? C2B C3B C13B 119.7(3) . . ? C9B C3B C13B 120.6(2) . . ? C5B C4B H4B 119.6 . . ? C5B C4B C9B 120.8(3) . . ? C9B C4B H4B 119.6 . . ? C4B C5B H5B 119.4 . . ? C4B C5B C6B 121.1(3) . . ? C6B C5B H5B 119.4 . . ? C5B C6B H6B 120.2 . . ? C7B C6B C5B 119.5(3) . . ? C7B C6B H6B 120.2 . . ? C6B C7B H7B 120.0 . . ? C6B C7B C8B 119.9(3) . . ? C8B C7B H7B 120.0 . . ? C7B C8B C1B 119.4(3) . . ? C7B C8B C9B 121.0(3) . . ? C9B C8B C1B 119.6(3) . . ? C4B C9B C3B 123.1(2) . . ? C4B C9B C8B 117.5(3) . . ? C8B C9B C3B 119.4(3) . . ? C2B C10B H10B 114.7 . . ? C2B C10B C11B 120.9(3) . . ? C2B C10B C12B 121.7(3) . . ? C11B C10B H10B 114.7 . . ? C12B C10B H10B 114.7 . . ? C12B C10B C11B 58.92(17) . . ? C10B C11B H11C 117.7 . . ? C10B C11B H11D 117.7 . . ? H11C C11B H11D 114.9 . . ? C12B C11B C10B 60.36(18) . . ? C12B C11B H11C 117.7 . . ? C12B C11B H11D 117.7 . . ? C10B C12B H12C 117.7 . . ? C10B C12B H12D 117.7 . . ? C11B C12B C10B 60.72(19) . . ? C11B C12B H12C 117.7 . . ? C11B C12B H12D 117.7 . . ? H12C C12B H12D 114.8 . . ? C14B C13B C3B 120.6(2) . . ? C14B C13B C18B 118.0(2) . . ? C18B C13B C3B 121.3(2) . . ? C13B C14B H14B 119.5 . . ? C13B C14B C15B 120.9(3) . . ? C15B C14B H14B 119.5 . . ? C14B C15B H15B 120.1 . . ? C16B C15B C14B 119.8(3) . . ? C16B C15B H15B 120.1 . . ? C15B C16B H16B 119.7 . . ? C17B C16B C15B 120.6(3) . . ? C17B C16B H16B 119.7 . . ? C16B C17B H17B 120.5 . . ? C16B C17B C18B 119.1(3) . . ? C18B C17B H17B 120.5 . . ? C13B C18B H18B 119.2 . . ? C17B C18B C13B 121.5(3) . . ? C17B C18B H18B 119.2 . . ? C1C O2C C2C 123.1(2) . . ? O1C C1C O2C 117.4(2) . . ? O1C C1C C8C 126.4(3) . . ? O2C C1C C8C 116.3(3) . . ? O2C C2C C10C 111.3(2) . . ? C3C C2C O2C 122.1(2) . . ? C3C C2C C10C 126.6(3) . . ? C2C C3C C9C 118.3(3) . . ? C2C C3C C13C 119.7(2) . . ? C9C C3C C13C 121.9(2) . . ? C5C C4C H4C 119.9 . . ? C5C C4C C9C 120.3(3) . . ? C9C C4C H4C 119.9 . . ? C4C C5C H5C 119.5 . . ? C4C C5C C6C 121.1(3) . . ? C6C C5C H5C 119.5 . . ? C5C C6C H6C 120.0 . . ? C5C C6C C7C 120.0(3) . . ? C7C C6C H6C 120.0 . . ? C6C C7C H7C 120.3 . . ? C6C C7C C8C 119.4(3) . . ? C8C C7C H7C 120.3 . . ? C7C C8C C1C 118.5(3) . . ? C9C C8C C1C 120.7(2) . . ? C9C C8C C7C 120.9(3) . . ? C4C C9C C3C 122.2(3) . . ? C8C C9C C3C 119.5(2) . . ? C8C C9C C4C 118.3(2) . . ? C2C C10C H10C 115.0 . . ? C2C C10C C11C 122.1(3) . . ? C2C C10C C12C 119.2(2) . . ? C11C C10C H10C 115.0 . . ? C11C C10C C12C 58.97(17) . . ? C12C C10C H10C 115.0 . . ? C10C C11C H11A 117.6 . . ? C10C C11C H11B 117.6 . . ? H11A C11C H11B 114.8 . . ? C12C C11C C10C 61.21(18) . . ? C12C C11C H11A 117.6 . . ? C12C C11C H11B 117.6 . . ? C10C C12C H12A 117.8 . . ? C10C C12C H12B 117.8 . . ? C11C C12C C10C 59.83(17) . . ? C11C C12C H12A 117.8 . . ? C11C C12C H12B 117.8 . . ? H12A C12C H12B 114.9 . . ? C14C C13C C3C 122.0(3) . . ? C18C C13C C3C 120.1(2) . . ? C18C C13C C14C 117.8(3) . . ? C13C C14C H14C 119.7 . . ? C15C C14C C13C 120.6(3) . . ? C15C C14C H14C 119.7 . . ? C14C C15C H15C 119.6 . . ? C16C C15C C14C 120.8(3) . . ? C16C C15C H15C 119.6 . . ? C15C C16C H16C 120.2 . . ? C15C C16C C17C 119.6(3) . . ? C17C C16C H16C 120.2 . . ? C16C C17C H17C 120.1 . . ? C16C C17C C18C 119.9(3) . . ? C18C C17C H17C 120.1 . . ? C13C C18C C17C 121.3(3) . . ? C13C C18C H18C 119.4 . . ? C17C C18C H18C 119.4 . . ? #==END data_8aa_dk85 _database_code_depnum_ccdc_archive 'CCDC 901340' #TrackingRef '- OBC_026250.cif' _audit_creation_date 2012-05-22 _audit_creation_method ; Olex2 1.2-beta (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common 4-cyclopropyl-2-methyl-3-phenylisoquinolin-1(2H)-one _chemical_name_systematic ; 4-cyclopropyl-2-methyl-3-phenylisoquinolin-1(2H)-one ; _chemical_formula_moiety 'C19 H17 N O' _chemical_formula_sum 'C19 H17 N O' _chemical_formula_weight 275.34 _chemical_melting_point '139-141 C' 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 8.6979(3) _cell_length_b 16.6842(5) _cell_length_c 10.4505(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.2930(10) _cell_angle_gamma 90.00 _cell_volume 1392.94(8) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6391 _cell_measurement_temperature 120 _cell_measurement_theta_max 30.97 _cell_measurement_theta_min 2.44 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.5436 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2006/1 (Bruker,2006) was used for absorption correction. R(int) was 0.0433 before and 0.0241 after correction. The Ratio of minimum to maximum transmission is 0.5436. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 584 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.25 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 3 sets of \w scans each set at different \f and/or 2\q angles and each scan (3 s exposure) covering -0.300\% degrees in \w. The crystal to detector distance was 4.85 cm. ; _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_unetI/netI 0.0220 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 17011 _diffrn_reflns_theta_full 29.50 _diffrn_reflns_theta_max 29.50 _diffrn_reflns_theta_min 2.44 _diffrn_ambient_temperature 120 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker SMART CCD 6000' _diffrn_measurement_method '/w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_target MO _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3174 _reflns_number_total 3877 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.428 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.054 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 258 _refine_ls_number_reflns 3877 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.0460 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.3300P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1237 _refine_ls_wR_factor_ref 0.1353 _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. ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 O1 O 0.03056(11) 0.69613(5) 0.28991(8) 0.0257(2) Uani 1 1 d . . . N1 N 0.20947(11) 0.66384(5) 0.51038(9) 0.01876(19) Uani 1 1 d . . . C1 C 0.10645(13) 0.64357(6) 0.37545(11) 0.0188(2) Uani 1 1 d . . . C2 C 0.08962(13) 0.55795(6) 0.34301(11) 0.0180(2) Uani 1 1 d . . . C3 C 0.16957(13) 0.50078(6) 0.44700(11) 0.0179(2) Uani 1 1 d . . . C4 C 0.28754(13) 0.52725(6) 0.58254(11) 0.0183(2) Uani 1 1 d . . . C5 C 0.30621(12) 0.60739(6) 0.60916(10) 0.0177(2) Uani 1 1 d . . . C6 C 0.38661(13) 0.46558(7) 0.68626(12) 0.0213(2) Uani 1 1 d . . . C7 C 0.50207(14) 0.40871(7) 0.65327(13) 0.0255(2) Uani 1 1 d . . . C8 C 0.57410(14) 0.47036(7) 0.76537(13) 0.0255(2) Uani 1 1 d . . . C9 C -0.01037(13) 0.53416(7) 0.20618(11) 0.0216(2) Uani 1 1 d . . . C10 C -0.03440(14) 0.45367(7) 0.17364(12) 0.0246(2) Uani 1 1 d . . . C11 C 0.03567(14) 0.39599(7) 0.27824(13) 0.0250(2) Uani 1 1 d . . . C12 C 0.13672(14) 0.41890(7) 0.41231(12) 0.0223(2) Uani 1 1 d . . . C13 C 0.43921(13) 0.64135(6) 0.73616(11) 0.0190(2) Uani 1 1 d . . . C14 C 0.56615(14) 0.68728(7) 0.72145(11) 0.0211(2) Uani 1 1 d . . . C15 C 0.69940(14) 0.71574(7) 0.83813(12) 0.0233(2) Uani 1 1 d . . . C16 C 0.70674(15) 0.69893(7) 0.97085(12) 0.0252(2) Uani 1 1 d . . . C17 C 0.58041(15) 0.65427(7) 0.98582(12) 0.0258(2) Uani 1 1 d . . . C18 C 0.44723(14) 0.62537(7) 0.86967(11) 0.0234(2) Uani 1 1 d . . . C19 C 0.20368(15) 0.74813(7) 0.54964(12) 0.0246(2) Uani 1 1 d . . . H6 H 0.3299(19) 0.4421(9) 0.7398(16) 0.027(4) Uiso 1 1 d . . . H7A H 0.516(2) 0.4201(10) 0.5656(18) 0.036(4) Uiso 1 1 d . . . H7B H 0.505(2) 0.3515(10) 0.6799(17) 0.034(4) Uiso 1 1 d . . . H8A H 0.623(2) 0.4534(9) 0.8648(18) 0.031(4) Uiso 1 1 d . . . H8B H 0.632(2) 0.5168(11) 0.7457(18) 0.039(5) Uiso 1 1 d . . . H9 H -0.056(2) 0.5775(10) 0.1341(17) 0.034(4) Uiso 1 1 d . . . H10 H -0.104(2) 0.4391(10) 0.0742(17) 0.031(4) Uiso 1 1 d . . . H11 H 0.013(2) 0.3391(10) 0.2558(18) 0.034(4) Uiso 1 1 d . . . H12 H 0.1877(19) 0.3769(10) 0.4836(17) 0.031(4) Uiso 1 1 d . . . H14 H 0.565(2) 0.6976(9) 0.6294(18) 0.032(4) Uiso 1 1 d . . . H15 H 0.7859(19) 0.7474(9) 0.8247(15) 0.026(4) Uiso 1 1 d . . . H16 H 0.799(2) 0.7181(10) 1.0530(19) 0.040(4) Uiso 1 1 d . . . H17 H 0.585(2) 0.6439(9) 1.0800(17) 0.032(4) Uiso 1 1 d . . . H18 H 0.3616(19) 0.5918(9) 0.8822(16) 0.029(4) Uiso 1 1 d . . . H19A H 0.231(2) 0.7528(11) 0.6503(19) 0.040(4) Uiso 1 1 d . . . H19B H 0.090(2) 0.7667(11) 0.4993(18) 0.040(4) Uiso 1 1 d . . . H19C H 0.282(2) 0.7799(11) 0.5262(19) 0.043(5) 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 O1 0.0275(4) 0.0218(4) 0.0207(4) 0.0028(3) 0.0020(3) 0.0049(3) N1 0.0186(4) 0.0176(4) 0.0165(4) 0.0002(3) 0.0032(3) 0.0016(3) C1 0.0177(5) 0.0195(5) 0.0174(5) 0.0005(4) 0.0050(4) 0.0016(4) C2 0.0150(4) 0.0197(5) 0.0175(5) -0.0005(4) 0.0045(4) 0.0006(3) C3 0.0154(4) 0.0191(5) 0.0183(5) 0.0002(4) 0.0059(4) 0.0001(3) C4 0.0164(4) 0.0209(5) 0.0165(5) 0.0019(4) 0.0052(4) 0.0011(4) C5 0.0157(4) 0.0212(5) 0.0143(4) 0.0017(3) 0.0040(4) 0.0009(4) C6 0.0183(5) 0.0227(5) 0.0214(5) 0.0061(4) 0.0062(4) 0.0021(4) C7 0.0217(5) 0.0215(5) 0.0306(6) 0.0035(4) 0.0074(4) 0.0028(4) C8 0.0186(5) 0.0275(6) 0.0247(5) 0.0035(4) 0.0026(4) 0.0030(4) C9 0.0180(5) 0.0250(5) 0.0188(5) -0.0007(4) 0.0040(4) 0.0011(4) C10 0.0197(5) 0.0280(6) 0.0226(5) -0.0060(4) 0.0044(4) -0.0019(4) C11 0.0208(5) 0.0223(5) 0.0299(6) -0.0045(4) 0.0078(4) -0.0022(4) C12 0.0202(5) 0.0189(5) 0.0263(5) 0.0002(4) 0.0077(4) -0.0006(4) C13 0.0174(5) 0.0203(5) 0.0162(4) -0.0003(4) 0.0034(4) 0.0009(4) C14 0.0208(5) 0.0228(5) 0.0187(5) -0.0001(4) 0.0066(4) 0.0000(4) C15 0.0195(5) 0.0214(5) 0.0260(5) -0.0019(4) 0.0058(4) -0.0003(4) C16 0.0232(5) 0.0235(5) 0.0217(5) -0.0024(4) 0.0011(4) 0.0024(4) C17 0.0283(6) 0.0282(6) 0.0161(5) 0.0011(4) 0.0038(4) 0.0022(4) C18 0.0231(5) 0.0272(5) 0.0183(5) 0.0012(4) 0.0064(4) -0.0009(4) C19 0.0252(6) 0.0195(5) 0.0239(5) -0.0020(4) 0.0040(4) 0.0030(4) _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 O1 C1 1.2398(13) . ? N1 C1 1.3807(13) . ? N1 C5 1.4049(13) . ? N1 C19 1.4714(14) . ? C1 C2 1.4621(15) . ? C2 C3 1.4060(14) . ? C2 C9 1.4054(14) . ? C3 C4 1.4509(14) . ? C3 C12 1.4133(15) . ? C4 C5 1.3622(15) . ? C4 C6 1.4958(14) . ? C5 C13 1.4854(14) . ? C6 C7 1.5170(16) . ? C6 C8 1.5110(16) . ? C6 H6 0.964(15) . ? C7 C8 1.4974(17) . ? C7 H7A 0.988(17) . ? C7 H7B 0.992(17) . ? C8 H8A 0.996(17) . ? C8 H8B 0.987(18) . ? C9 C10 1.3809(16) . ? C9 H9 1.005(17) . ? C10 C11 1.4020(17) . ? C10 H10 1.004(16) . ? C11 C12 1.3812(16) . ? C11 H11 0.978(17) . ? C12 H12 0.991(16) . ? C13 C14 1.4015(15) . ? C13 C18 1.3949(15) . ? C14 C15 1.3921(15) . ? C14 H14 0.974(17) . ? C15 C16 1.3916(17) . ? C15 H15 0.973(15) . ? C16 C17 1.3867(18) . ? C16 H16 0.968(19) . ? C17 C18 1.3913(15) . ? C17 H17 0.984(17) . ? C18 H18 0.981(16) . ? C19 H19A 0.986(17) . ? C19 H19B 0.969(18) . ? C19 H19C 0.969(19) . ? 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 C1 N1 C5 122.99(9) . . ? C1 N1 C19 116.03(9) . . ? C5 N1 C19 120.82(9) . . ? O1 C1 N1 120.57(10) . . ? O1 C1 C2 123.23(10) . . ? N1 C1 C2 116.17(9) . . ? C3 C2 C1 120.67(9) . . ? C9 C2 C1 118.47(10) . . ? C9 C2 C3 120.85(10) . . ? C2 C3 C4 119.39(9) . . ? C2 C3 C12 118.00(10) . . ? C12 C3 C4 122.54(10) . . ? C3 C4 C6 118.71(9) . . ? C5 C4 C3 118.64(9) . . ? C5 C4 C6 122.63(10) . . ? N1 C5 C13 115.43(9) . . ? C4 C5 N1 121.30(9) . . ? C4 C5 C13 123.00(9) . . ? C4 C6 C7 120.59(10) . . ? C4 C6 C8 123.23(10) . . ? C4 C6 H6 114.8(9) . . ? C7 C6 H6 114.5(9) . . ? C8 C6 C7 59.28(8) . . ? C8 C6 H6 113.2(9) . . ? C6 C7 H7A 115.1(10) . . ? C6 C7 H7B 118.8(9) . . ? C8 C7 C6 60.16(8) . . ? C8 C7 H7A 115.3(10) . . ? C8 C7 H7B 119.1(10) . . ? H7A C7 H7B 116.5(13) . . ? C6 C8 H8A 118.5(9) . . ? C6 C8 H8B 117.0(10) . . ? C7 C8 C6 60.56(8) . . ? C7 C8 H8A 119.7(9) . . ? C7 C8 H8B 117.8(10) . . ? H8A C8 H8B 113.5(14) . . ? C2 C9 H9 117.4(10) . . ? C10 C9 C2 119.85(10) . . ? C10 C9 H9 122.6(9) . . ? C9 C10 C11 119.92(11) . . ? C9 C10 H10 117.4(9) . . ? C11 C10 H10 122.7(9) . . ? C10 C11 H11 119.6(10) . . ? C12 C11 C10 120.47(11) . . ? C12 C11 H11 119.9(10) . . ? C3 C12 H12 120.4(9) . . ? C11 C12 C3 120.71(10) . . ? C11 C12 H12 118.9(9) . . ? C14 C13 C5 118.65(9) . . ? C18 C13 C5 122.28(10) . . ? C18 C13 C14 118.97(10) . . ? C13 C14 H14 120.4(10) . . ? C15 C14 C13 120.63(10) . . ? C15 C14 H14 118.9(10) . . ? C14 C15 H15 118.8(9) . . ? C16 C15 C14 119.90(11) . . ? C16 C15 H15 121.3(9) . . ? C15 C16 H16 120.9(11) . . ? C17 C16 C15 119.64(10) . . ? C17 C16 H16 119.4(10) . . ? C16 C17 C18 120.75(11) . . ? C16 C17 H17 119.1(10) . . ? C18 C17 H17 120.2(10) . . ? C13 C18 H18 120.2(9) . . ? C17 C18 C13 120.10(11) . . ? C17 C18 H18 119.7(9) . . ? N1 C19 H19A 110.6(10) . . ? N1 C19 H19B 107.1(11) . . ? N1 C19 H19C 110.3(11) . . ? H19A C19 H19B 108.4(15) . . ? H19A C19 H19C 109.4(15) . . ? H19B C19 H19C 111.0(15) . . ? #==END data_8ah_dk88 _database_code_depnum_ccdc_archive 'CCDC 901341' #TrackingRef '- OBC_026250.cif' _audit_creation_date 2012-06-08 _audit_creation_method ; Olex2 1.2-beta (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common 4-cyclopropyl-2-methyl-3-(n-propyl)-isoquinolin-1(2H)-one _chemical_name_systematic ; 4-cyclopropyl-2-methyl-3-(n-propyl)-isoquinolin-1(2H)-one ; _chemical_formula_moiety 'C16 H19 N O' _chemical_formula_sum 'C16 H19 N O' _chemical_formula_weight 241.32 _chemical_melting_point ? 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 7.9056(4) _cell_length_b 8.8734(5) _cell_length_c 9.7298(5) _cell_angle_alpha 96.304(2) _cell_angle_beta 100.043(2) _cell_angle_gamma 108.110(2) _cell_volume 628.90(6) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2375 _cell_measurement_temperature 120 _cell_measurement_theta_max 30.98 _cell_measurement_theta_min 2.16 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_T_max . _exptl_absorpt_correction_T_min . _exptl_absorpt_correction_type none _exptl_absorpt_process_details . _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 260 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 2 sets of \w scans each set at different \f and/or 2\q angles and each scan (5 s exposure) covering -0.300\% degrees in \w. The crystal to detector distance was 4.85 cm. ; _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_unetI/netI 0.0513 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 10556 _diffrn_reflns_theta_full 29.00 _diffrn_reflns_theta_max 29.00 _diffrn_reflns_theta_min 2.16 _diffrn_ambient_temperature 120 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker SMART CCD 6000' _diffrn_measurement_method '/w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_current 10.0 _diffrn_source_power 0.3 _diffrn_source_target MO _diffrn_source_voltage 30.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2073 _reflns_number_total 3344 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.528 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.068 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 239 _refine_ls_number_reflns 3344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0885 _refine_ls_R_factor_gt 0.0582 _refine_ls_restrained_S_all 0.980 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1463 _refine_ls_wR_factor_ref 0.1688 _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. ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 O1 O 0.12518(16) 0.75904(14) 1.13653(12) 0.0292(3) Uani 1 1 d . . . N1 N 0.22293(17) 0.80231(15) 0.93249(13) 0.0207(3) Uani 1 1 d . . . C1 C 0.1816(2) 0.85522(19) 1.05843(16) 0.0209(3) Uani 1 1 d . . . C2 C 0.21365(19) 1.02730(18) 1.09200(16) 0.0197(3) Uani 1 1 d . . . C3 C 0.27719(19) 1.13045(18) 0.99879(15) 0.0192(3) Uani 1 1 d . . . C4 C 0.30683(19) 1.06424(18) 0.86559(15) 0.0196(3) Uani 1 1 d . . . C5 C 0.2851(2) 0.90426(19) 0.83812(15) 0.0198(3) Uani 1 1 d . . . C6 C 0.3684(2) 1.17387(19) 0.76403(16) 0.0222(3) Uani 1 1 d . . . C7 C 0.2591(3) 1.2775(2) 0.71096(18) 0.0290(4) Uani 1 1 d . . . C8 C 0.2654(3) 1.1387(2) 0.61113(18) 0.0298(4) Uani 1 1 d . . . C9 C 0.1821(2) 1.0875(2) 1.22173(16) 0.0230(3) Uani 1 1 d . . . C10 C 0.2164(2) 1.2503(2) 1.25993(17) 0.0251(4) Uani 1 1 d . . . C11 C 0.2826(2) 1.3551(2) 1.16908(17) 0.0255(4) Uani 1 1 d . . . C12 C 0.3122(2) 1.29655(19) 1.04089(17) 0.0230(3) Uani 1 1 d . . . C13 C 0.3357(2) 0.8316(2) 0.71029(16) 0.0231(3) Uani 1 1 d . . . C14 C 0.1798(2) 0.7235(2) 0.58818(18) 0.0283(4) Uani 1 1 d . . . C15 C 0.2537(3) 0.6760(3) 0.4619(2) 0.0375(5) Uani 1 1 d . . . C16 C 0.1957(3) 0.6294(2) 0.90541(19) 0.0275(4) Uani 1 1 d . . . H6 H 0.500(3) 1.223(2) 0.7770(19) 0.025(4) Uiso 1 1 d . . . H7A H 0.150(3) 1.262(2) 0.744(2) 0.036(5) Uiso 1 1 d . . . H7B H 0.319(3) 1.384(3) 0.693(2) 0.035(5) Uiso 1 1 d . . . H8A H 0.336(3) 1.162(2) 0.535(2) 0.035(5) Uiso 1 1 d . . . H8B H 0.156(3) 1.047(2) 0.5859(19) 0.027(5) Uiso 1 1 d . . . H9 H 0.138(2) 1.009(2) 1.2837(19) 0.022(4) Uiso 1 1 d . . . H10 H 0.199(3) 1.294(2) 1.352(2) 0.036(5) Uiso 1 1 d . . . H11 H 0.306(3) 1.468(2) 1.197(2) 0.030(5) Uiso 1 1 d . . . H12 H 0.358(2) 1.372(2) 0.9781(19) 0.023(4) Uiso 1 1 d . . . H13A H 0.411(2) 0.925(2) 0.6742(18) 0.026(5) Uiso 1 1 d . . . H13B H 0.418(2) 0.771(2) 0.7434(18) 0.024(4) Uiso 1 1 d . . . H14A H 0.093(3) 0.783(2) 0.5607(19) 0.030(5) Uiso 1 1 d . . . H14B H 0.112(3) 0.629(2) 0.6177(19) 0.027(5) Uiso 1 1 d . . . H15A H 0.340(3) 0.619(3) 0.489(2) 0.052(6) Uiso 1 1 d . . . H15B H 0.318(3) 0.773(3) 0.426(2) 0.040(6) Uiso 1 1 d . . . H15C H 0.161(3) 0.609(3) 0.383(2) 0.043(6) Uiso 1 1 d . . . H16A H 0.233(3) 0.595(3) 0.990(2) 0.045(6) Uiso 1 1 d . . . H16B H 0.070(4) 0.566(3) 0.866(3) 0.060(7) Uiso 1 1 d . . . H16C H 0.267(4) 0.606(3) 0.841(3) 0.066(8) 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 O1 0.0349(7) 0.0257(6) 0.0284(6) 0.0097(5) 0.0112(5) 0.0083(5) N1 0.0224(6) 0.0180(7) 0.0206(6) 0.0037(5) 0.0034(5) 0.0056(5) C1 0.0189(7) 0.0227(8) 0.0197(7) 0.0051(6) 0.0022(6) 0.0058(6) C2 0.0171(7) 0.0203(8) 0.0211(7) 0.0046(6) 0.0025(5) 0.0060(6) C3 0.0170(7) 0.0207(8) 0.0195(7) 0.0035(6) 0.0025(5) 0.0068(6) C4 0.0183(7) 0.0209(8) 0.0189(7) 0.0045(6) 0.0029(5) 0.0058(6) C5 0.0166(7) 0.0227(8) 0.0189(7) 0.0033(6) 0.0017(5) 0.0063(6) C6 0.0230(8) 0.0217(8) 0.0214(7) 0.0039(6) 0.0052(6) 0.0064(6) C7 0.0345(9) 0.0293(10) 0.0269(9) 0.0104(7) 0.0094(7) 0.0125(8) C8 0.0339(9) 0.0330(10) 0.0214(8) 0.0070(7) 0.0050(7) 0.0093(8) C9 0.0200(7) 0.0285(9) 0.0208(7) 0.0061(6) 0.0049(6) 0.0077(6) C10 0.0235(8) 0.0310(9) 0.0206(8) -0.0003(7) 0.0046(6) 0.0109(7) C11 0.0261(8) 0.0227(9) 0.0275(8) 0.0017(7) 0.0039(6) 0.0101(7) C12 0.0232(8) 0.0228(8) 0.0238(8) 0.0054(6) 0.0048(6) 0.0085(6) C13 0.0240(8) 0.0233(8) 0.0214(8) 0.0008(6) 0.0050(6) 0.0082(7) C14 0.0272(8) 0.0297(9) 0.0247(8) 0.0000(7) 0.0057(7) 0.0066(7) C15 0.0376(10) 0.0419(12) 0.0269(9) -0.0051(8) 0.0085(8) 0.0076(9) C16 0.0339(9) 0.0199(8) 0.0292(9) 0.0050(7) 0.0078(7) 0.0092(7) _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 O1 C1 1.2364(18) . ? N1 C1 1.392(2) . ? N1 C5 1.4024(19) . ? N1 C16 1.468(2) . ? C1 C2 1.457(2) . ? C2 C3 1.403(2) . ? C2 C9 1.409(2) . ? C3 C4 1.451(2) . ? C3 C12 1.411(2) . ? C4 C5 1.366(2) . ? C4 C6 1.498(2) . ? C5 C13 1.510(2) . ? C6 C7 1.517(2) . ? C6 C8 1.514(2) . ? C6 H6 0.973(19) . ? C7 C8 1.501(3) . ? C7 H7A 0.95(2) . ? C7 H7B 0.97(2) . ? C8 H8A 1.00(2) . ? C8 H8B 0.96(2) . ? C9 C10 1.379(2) . ? C9 H9 0.992(18) . ? C10 C11 1.400(2) . ? C10 H10 0.98(2) . ? C11 C12 1.384(2) . ? C11 H11 0.96(2) . ? C12 H12 0.984(19) . ? C13 C14 1.535(2) . ? C13 H13A 0.995(18) . ? C13 H13B 1.002(18) . ? C14 C15 1.522(3) . ? C14 H14A 1.005(19) . ? C14 H14B 0.950(19) . ? C15 H15A 0.99(2) . ? C15 H15B 0.99(2) . ? C15 H15C 0.96(2) . ? C16 H16A 0.94(2) . ? C16 H16B 0.96(3) . ? C16 H16C 0.96(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 C1 N1 C5 123.34(13) . . ? C1 N1 C16 114.47(13) . . ? C5 N1 C16 122.20(13) . . ? O1 C1 N1 120.32(14) . . ? O1 C1 C2 123.49(14) . . ? N1 C1 C2 116.17(13) . . ? C3 C2 C1 120.87(14) . . ? C3 C2 C9 120.97(14) . . ? C9 C2 C1 118.15(14) . . ? C2 C3 C4 119.53(13) . . ? C2 C3 C12 117.74(14) . . ? C12 C3 C4 122.73(13) . . ? C3 C4 C6 119.39(13) . . ? C5 C4 C3 119.16(13) . . ? C5 C4 C6 121.40(14) . . ? N1 C5 C13 117.27(13) . . ? C4 C5 N1 120.74(14) . . ? C4 C5 C13 121.91(14) . . ? C4 C6 C7 120.60(14) . . ? C4 C6 C8 121.21(14) . . ? C4 C6 H6 115.7(10) . . ? C7 C6 H6 114.5(10) . . ? C8 C6 C7 59.39(11) . . ? C8 C6 H6 113.8(10) . . ? C6 C7 H7A 114.2(12) . . ? C6 C7 H7B 121.1(12) . . ? C8 C7 C6 60.20(11) . . ? C8 C7 H7A 116.4(12) . . ? C8 C7 H7B 116.5(12) . . ? H7A C7 H7B 116.6(17) . . ? C6 C8 H8A 118.9(12) . . ? C6 C8 H8B 115.8(11) . . ? C7 C8 C6 60.42(11) . . ? C7 C8 H8A 118.7(12) . . ? C7 C8 H8B 115.4(11) . . ? H8A C8 H8B 116.1(16) . . ? C2 C9 H9 117.6(10) . . ? C10 C9 C2 120.11(14) . . ? C10 C9 H9 122.2(10) . . ? C9 C10 C11 119.58(15) . . ? C9 C10 H10 120.6(12) . . ? C11 C10 H10 119.8(12) . . ? C10 C11 H11 118.9(11) . . ? C12 C11 C10 120.60(15) . . ? C12 C11 H11 120.5(11) . . ? C3 C12 H12 119.5(11) . . ? C11 C12 C3 120.99(15) . . ? C11 C12 H12 119.5(11) . . ? C5 C13 C14 117.66(13) . . ? C5 C13 H13A 105.5(10) . . ? C5 C13 H13B 108.2(10) . . ? C14 C13 H13A 109.0(10) . . ? C14 C13 H13B 109.4(10) . . ? H13A C13 H13B 106.5(14) . . ? C13 C14 H14A 108.7(11) . . ? C13 C14 H14B 110.7(11) . . ? C15 C14 C13 110.79(14) . . ? C15 C14 H14A 110.6(11) . . ? C15 C14 H14B 109.1(11) . . ? H14A C14 H14B 106.9(16) . . ? C14 C15 H15A 110.9(13) . . ? C14 C15 H15B 110.2(12) . . ? C14 C15 H15C 113.7(13) . . ? H15A C15 H15B 108.6(18) . . ? H15A C15 H15C 107.9(19) . . ? H15B C15 H15C 105.3(17) . . ? N1 C16 H16A 110.3(13) . . ? N1 C16 H16B 111.8(15) . . ? N1 C16 H16C 111.0(16) . . ? H16A C16 H16B 107.8(19) . . ? H16A C16 H16C 107(2) . . ? H16B C16 H16C 108(2) . . ?