data_crystal_005 _audit_creation_date 2013-08-20 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:59:47, GUI svn.r4466) ; _publ_contact_author_address ? _publ_contact_author_email ? _publ_contact_author_name '' _publ_contact_author_phone ? _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C27 H22 Cl F O, C0.58 H1.16 Cl1.16' _chemical_formula_sum 'C27.58 H23.16 Cl2.16 F O' _chemical_formula_weight 466.24 _chemical_absolute_configuration ad _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' 'Cl' 'Cl' 0.1484 0.1585 '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 4 _space_group_name_H-M_alt 'P 1 21 1' _space_group_name_Hall 'P 2yb' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.4485(6) _cell_length_b 5.9142(3) _cell_length_c 17.0352(8) _cell_angle_alpha 90 _cell_angle_beta 91.076(3) _cell_angle_gamma 90 _cell_volume 1153.23(10) _cell_formula_units_Z 2 _cell_measurement_reflns_used 9971 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 29.48 _cell_measurement_theta_min 2.16 _exptl_absorpt_coefficient_mu 0.326 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type 'none' _exptl_absorpt_process_details ? _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_meas . _exptl_crystal_density_method ? _exptl_crystal_description needle _exptl_crystal_F_000 484.8 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_special_details ; ? ; _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0601 _diffrn_reflns_av_unetI/netI 0.0730 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.955 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 62094 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.938 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 37.564 _diffrn_reflns_theta_min 1.779 _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.955 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'graphite' _diffrn_radiation_type 'MoK\a' _diffrn_radiation_wavelength 0.71073 _diffrn_source ? _diffrn_standards_number 0 _reflns_Friedel_coverage 0.828 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 0.918 _reflns_number_gt 8151 _reflns_number_total 11432 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction 'SAINT v8.27A (Bruker, 2012)' _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 ; SHELXL, 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 0.818 _refine_diff_density_min -0.637 _refine_diff_density_rms 0.070 _refine_ls_abs_structure_details ; Flack x determined using 3069 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack -0.005(18) _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.957 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 321 _refine_ls_number_reflns 11432 _refine_ls_number_restraints 68 _refine_ls_R_factor_all 0.0773 _refine_ls_R_factor_gt 0.0499 _refine_ls_restrained_S_all 0.989 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0717P)^2^] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1202 _refine_ls_wR_factor_ref 0.1290 _refine_special_details ; ? ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All O(H) groups 2. Restrained distances C28-Cl2 \\sim C28-Cl3A \\sim C28-Cl3B \\sim C28-Cl3C with sigma of 0.01 3. Uiso/Uaniso restraints and constraints Cl3A \\sim Cl3B \\sim Cl3C \\sim Cl2 \\sim C28: within 3.2A with sigma of 0.01 and sigma for terminal atoms of 0.005 4. Others 1*[Sof(Cl3A)]+1*[Sof(Cl3B)]+1*[Sof(Cl3C)]-1*[Sof(Cl2)+Sof(C28)+Sof(H28A)+ Sof(H28B)]=0 with esd of 0.0001 Sof(Cl2)=Sof(C28)=Sof(H28A)=Sof(H28B)=FVAR(4) 5.a Secondary CH2 refined with riding coordinates: C9(H9A,H9B), C28(H28A,H28B) 5.b Aromatic/amide H refined with riding coordinates: C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27) 5.c Idealised tetrahedral OH refined as rotating group: O1(H1) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary ? 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl -0.31493(6) -0.81130(11) -0.38253(3) 0.03278(15) Uani 1 1 d . . . . . F1 F -0.31729(10) -0.90033(18) -0.78646(6) 0.0137(2) Uani 1 1 d . . . . . O1 O -0.33902(12) -0.3198(2) -0.72344(7) 0.0161(2) Uani 1 1 d . . . . . H1 H -0.3514 -0.2623 -0.7679 0.024 Uiso 1 1 calc R U . . . C1 C -0.28719(16) -0.6682(3) -0.78564(10) 0.0113(3) Uani 1 1 d . . . . . C2 C -0.37037(16) -0.5518(3) -0.72529(10) 0.0120(3) Uani 1 1 d . . . . . C3 C -0.30902(16) -0.5802(3) -0.86860(10) 0.0121(3) Uani 1 1 d . . . . . C4 C -0.26518(17) -0.3711(3) -0.89297(11) 0.0157(3) Uani 1 1 d . . . . . H4 H -0.2218 -0.2799 -0.8569 0.019 Uiso 1 1 calc R U . . . C5 C -0.28463(17) -0.2956(4) -0.96980(10) 0.0184(3) Uani 1 1 d . . . . . H5 H -0.2556 -0.1525 -0.9856 0.022 Uiso 1 1 calc R U . . . C6 C -0.34638(18) -0.4295(4) -1.02318(11) 0.0209(4) Uani 1 1 d . . . . . H6 H -0.3580 -0.3801 -1.0758 0.025 Uiso 1 1 calc R U . . . C7 C -0.39096(18) -0.6353(4) -0.99926(11) 0.0200(4) Uani 1 1 d . . . . . H7 H -0.4342 -0.7261 -1.0355 0.024 Uiso 1 1 calc R U . . . C8 C -0.37296(16) -0.7103(3) -0.92240(11) 0.0153(3) Uani 1 1 d . . . . . H8 H -0.4045 -0.8513 -0.9066 0.018 Uiso 1 1 calc R U . . . C9 C -0.15793(16) -0.6523(3) -0.76068(10) 0.0143(3) Uani 1 1 d . . . . . H9A H -0.1306 -0.4954 -0.7689 0.017 Uiso 1 1 calc R U . . . H9B H -0.1504 -0.6860 -0.7039 0.017 Uiso 1 1 calc R U . . . C10 C -0.08038(15) -0.8115(4) -0.80519(10) 0.0149(3) Uani 1 1 d . . . . . C11 C -0.04908(17) -0.7697(4) -0.88299(11) 0.0203(4) Uani 1 1 d . . . . . H11 H -0.0765 -0.6370 -0.9088 0.024 Uiso 1 1 calc R U . . . C12 C 0.02155(19) -0.9199(5) -0.92265(13) 0.0270(5) Uani 1 1 d . . . . . H12 H 0.0418 -0.8893 -0.9754 0.032 Uiso 1 1 calc R U . . . C13 C 0.06293(18) -1.1144(4) -0.88624(14) 0.0252(5) Uani 1 1 d . . . . . H13 H 0.1103 -1.2177 -0.9141 0.030 Uiso 1 1 calc R U . . . C14 C 0.03469(18) -1.1570(4) -0.80903(14) 0.0239(4) Uani 1 1 d . . . . . H14 H 0.0642 -1.2882 -0.7833 0.029 Uiso 1 1 calc R U . . . C15 C -0.03712(18) -1.0072(4) -0.76881(13) 0.0206(4) Uani 1 1 d . . . . . H15 H -0.0568 -1.0386 -0.7160 0.025 Uiso 1 1 calc R U . . . C16 C -0.35313(16) -0.6300(3) -0.63983(10) 0.0128(3) Uani 1 1 d . . . . . C17 C -0.38434(19) -0.4760(3) -0.58130(11) 0.0179(4) Uani 1 1 d . . . . . H17 H -0.4133 -0.3313 -0.5961 0.022 Uiso 1 1 calc R U . . . C18 C -0.3740(2) -0.5302(4) -0.50224(12) 0.0218(4) Uani 1 1 d . . . . . H18 H -0.3958 -0.4242 -0.4633 0.026 Uiso 1 1 calc R U . . . C19 C -0.33126(19) -0.7411(4) -0.48100(11) 0.0197(4) Uani 1 1 d . . . . . C20 C -0.30217(19) -0.8995(4) -0.53731(11) 0.0193(4) Uani 1 1 d . . . . . H20 H -0.2745 -1.0447 -0.5221 0.023 Uiso 1 1 calc R U . . . C21 C -0.31400(18) -0.8431(3) -0.61681(10) 0.0168(4) Uani 1 1 d . . . . . H21 H -0.2951 -0.9518 -0.6556 0.020 Uiso 1 1 calc R U . . . C22 C -0.49825(16) -0.5871(3) -0.75066(10) 0.0127(3) Uani 1 1 d . . . . . C23 C -0.55924(18) -0.4212(3) -0.79247(11) 0.0172(3) Uani 1 1 d . . . . . H23 H -0.5205 -0.2853 -0.8064 0.021 Uiso 1 1 calc R U . . . C24 C -0.67615(19) -0.4514(4) -0.81413(12) 0.0208(4) Uani 1 1 d . . . . . H24 H -0.7162 -0.3364 -0.8428 0.025 Uiso 1 1 calc R U . . . C25 C -0.73431(18) -0.6478(4) -0.79423(12) 0.0207(4) Uani 1 1 d . . . . . H25 H -0.8143 -0.6676 -0.8084 0.025 Uiso 1 1 calc R U . . . C26 C -0.67386(17) -0.8158(4) -0.75311(11) 0.0199(4) Uani 1 1 d . . . . . H26 H -0.7127 -0.9519 -0.7396 0.024 Uiso 1 1 calc R U . . . C27 C -0.55746(17) -0.7861(3) -0.73170(10) 0.0165(3) Uani 1 1 d . . . . . H27 H -0.5174 -0.9025 -0.7038 0.020 Uiso 1 1 calc R U . . . Cl2 Cl 0.0762(3) -1.8036(7) -0.57673(18) 0.1355(13) Uani 0.581(3) 1 d D U P A 1 Cl3A Cl -0.0738(8) -1.365(2) -0.5696(6) 0.156(2) Uani 0.235(3) 1 d D U P A 1 C28 C 0.0381(9) -1.5326(17) -0.5956(7) 0.141(2) Uani 0.581(3) 1 d D U P A 1 H28A H 0.1081 -1.4455 -0.5790 0.169 Uiso 0.581(3) 1 calc R U P A 1 H28B H 0.0363 -1.5250 -0.6537 0.169 Uiso 0.581(3) 1 calc R U P A 1 Cl3B Cl 0.0144(19) -1.292(4) -0.5390(13) 0.158(3) Uani 0.106(3) 1 d D U P B 2 Cl3C Cl -0.0295(9) -1.504(2) -0.5084(6) 0.169(3) Uani 0.240(3) 1 d D U P C 3 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 Cl1 0.0605(4) 0.0288(3) 0.00908(17) 0.0040(2) 0.00046(19) -0.0099(3) F1 0.0207(5) 0.0069(4) 0.0137(5) 0.0001(4) 0.0014(4) -0.0007(4) O1 0.0284(7) 0.0074(5) 0.0126(5) 0.0004(5) 0.0032(5) -0.0005(5) C1 0.0159(7) 0.0074(7) 0.0106(7) -0.0004(6) 0.0012(6) -0.0001(6) C2 0.0194(8) 0.0075(7) 0.0091(7) 0.0001(5) 0.0013(6) 0.0001(6) C3 0.0149(7) 0.0114(7) 0.0102(7) 0.0008(6) 0.0036(6) 0.0017(6) C4 0.0185(8) 0.0139(8) 0.0149(7) 0.0017(6) 0.0033(6) 0.0000(7) C5 0.0211(9) 0.0182(8) 0.0162(7) 0.0063(7) 0.0063(6) 0.0028(8) C6 0.0218(9) 0.0288(11) 0.0123(7) 0.0058(7) 0.0032(7) 0.0046(8) C7 0.0220(9) 0.0274(10) 0.0107(7) -0.0001(7) 0.0005(6) 0.0000(8) C8 0.0175(8) 0.0160(8) 0.0123(7) -0.0002(6) 0.0024(6) -0.0007(7) C9 0.0169(8) 0.0135(7) 0.0124(7) -0.0013(6) 0.0004(6) 0.0003(7) C10 0.0131(7) 0.0167(8) 0.0148(7) -0.0009(7) -0.0003(5) -0.0005(7) C11 0.0174(8) 0.0264(11) 0.0170(8) 0.0023(7) -0.0002(6) 0.0043(8) C12 0.0194(9) 0.0433(14) 0.0183(9) -0.0048(9) 0.0018(7) 0.0095(10) C13 0.0156(8) 0.0287(11) 0.0312(11) -0.0088(9) -0.0013(8) 0.0050(8) C14 0.0186(9) 0.0177(9) 0.0355(11) 0.0001(9) 0.0015(8) 0.0020(8) C15 0.0192(9) 0.0197(9) 0.0229(9) 0.0028(7) 0.0018(7) 0.0008(7) C16 0.0177(8) 0.0112(7) 0.0097(7) -0.0002(6) 0.0017(6) -0.0019(6) C17 0.0266(10) 0.0145(8) 0.0128(7) -0.0017(6) 0.0032(7) 0.0007(7) C18 0.0342(11) 0.0195(9) 0.0119(8) -0.0030(7) 0.0052(7) -0.0014(8) C19 0.0295(10) 0.0199(9) 0.0098(7) 0.0031(6) 0.0003(7) -0.0070(8) C20 0.0308(10) 0.0141(8) 0.0128(7) 0.0027(7) -0.0007(7) -0.0025(8) C21 0.0268(9) 0.0123(8) 0.0114(7) 0.0003(6) 0.0012(6) -0.0014(7) C22 0.0171(8) 0.0129(7) 0.0081(6) -0.0014(6) 0.0029(6) 0.0025(6) C23 0.0218(9) 0.0157(8) 0.0143(7) 0.0033(7) 0.0036(6) 0.0043(7) C24 0.0225(9) 0.0241(10) 0.0159(8) 0.0008(7) 0.0006(7) 0.0086(8) C25 0.0186(8) 0.0272(10) 0.0164(8) -0.0058(8) 0.0005(7) 0.0037(8) C26 0.0210(9) 0.0207(9) 0.0179(7) -0.0034(8) 0.0014(6) -0.0021(8) C27 0.0211(8) 0.0139(8) 0.0146(7) -0.0004(7) 0.0009(6) 0.0007(7) Cl2 0.132(2) 0.156(3) 0.116(2) -0.063(2) -0.0623(16) 0.026(2) Cl3A 0.136(4) 0.181(4) 0.150(4) -0.049(4) -0.042(3) 0.003(4) C28 0.105(4) 0.181(5) 0.134(4) -0.052(5) -0.065(4) 0.002(4) Cl3B 0.139(5) 0.183(5) 0.151(5) -0.041(5) -0.049(4) 0.010(5) Cl3C 0.140(4) 0.189(5) 0.176(5) -0.036(5) -0.037(4) 0.002(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 Cl1 C19 1.7347(19) . ? F1 C1 1.416(2) . ? O1 C2 1.419(2) . ? C1 C2 1.573(2) . ? C1 C3 1.522(2) . ? C1 C9 1.535(2) . ? C2 C16 1.537(2) . ? C2 C22 1.533(3) . ? C3 C4 1.400(3) . ? C3 C8 1.394(3) . ? C4 C5 1.397(3) . ? C5 C6 1.389(3) . ? C6 C7 1.384(3) . ? C7 C8 1.394(3) . ? C9 C10 1.508(3) . ? C10 C11 1.402(3) . ? C10 C15 1.399(3) . ? C11 C12 1.386(3) . ? C12 C13 1.386(4) . ? C13 C14 1.383(3) . ? C14 C15 1.397(3) . ? C16 C17 1.402(3) . ? C16 C21 1.392(3) . ? C17 C18 1.387(3) . ? C18 C19 1.386(3) . ? C19 C20 1.386(3) . ? C20 C21 1.399(3) . ? C22 C23 1.393(3) . ? C22 C27 1.399(3) . ? C23 C24 1.393(3) . ? C24 C25 1.384(3) . ? C25 C26 1.392(3) . ? C26 C27 1.386(3) . ? Cl2 C28 1.691(10) . ? Cl3A C28 1.687(11) . ? 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 F1 C1 C2 106.29(13) . . ? F1 C1 C3 106.66(14) . . ? F1 C1 C9 107.18(14) . . ? C3 C1 C2 111.50(14) . . ? C3 C1 C9 112.15(14) . . ? C9 C1 C2 112.61(14) . . ? O1 C2 C1 106.35(14) . . ? O1 C2 C16 104.00(14) . . ? O1 C2 C22 112.20(15) . . ? C16 C2 C1 114.78(14) . . ? C22 C2 C1 110.06(14) . . ? C22 C2 C16 109.34(14) . . ? C4 C3 C1 121.57(16) . . ? C8 C3 C1 119.78(16) . . ? C8 C3 C4 118.64(16) . . ? C5 C4 C3 120.55(18) . . ? C6 C5 C4 120.1(2) . . ? C7 C6 C5 119.63(18) . . ? C6 C7 C8 120.50(19) . . ? C3 C8 C7 120.55(19) . . ? C10 C9 C1 113.33(15) . . ? C11 C10 C9 121.90(18) . . ? C15 C10 C9 120.05(16) . . ? C15 C10 C11 118.05(18) . . ? C12 C11 C10 120.6(2) . . ? C11 C12 C13 120.8(2) . . ? C14 C13 C12 119.5(2) . . ? C13 C14 C15 120.1(2) . . ? C14 C15 C10 120.9(2) . . ? C17 C16 C2 116.65(16) . . ? C21 C16 C2 125.05(16) . . ? C21 C16 C17 118.23(17) . . ? C18 C17 C16 121.49(19) . . ? C19 C18 C17 119.00(19) . . ? C18 C19 Cl1 119.94(16) . . ? C18 C19 C20 121.06(18) . . ? C20 C19 Cl1 119.00(17) . . ? C19 C20 C21 119.28(19) . . ? C16 C21 C20 120.90(17) . . ? C23 C22 C2 121.02(17) . . ? C23 C22 C27 118.07(18) . . ? C27 C22 C2 120.91(16) . . ? C22 C23 C24 121.01(19) . . ? C25 C24 C23 120.45(19) . . ? C24 C25 C26 119.03(19) . . ? C27 C26 C25 120.6(2) . . ? C26 C27 C22 120.89(19) . . ? Cl3A C28 Cl2 134.6(11) . . ? _shelx_estimated_absorpt_T_max ? _shelx_estimated_absorpt_T_min ? _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelxl_version_number 2013-2 #============================================================================== # Schley, Caltech 8/20/2013