data_TMF+CMF _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H19.25 Cl O' _chemical_formula_weight 335.07 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.5966(8) _cell_length_b 12.5450(13) _cell_length_c 18.2688(18) _cell_angle_alpha 90.00 _cell_angle_beta 95.684(2) _cell_angle_gamma 90.00 _cell_volume 1732.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6053 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 26.02 _exptl_crystal_description 'block' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 705 _exptl_absorpt_coefficient_mu 0.225 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9193 _exptl_absorpt_correction_T_max 0.9355 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17513 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_sigmaI/netI 0.0169 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 26.03 _reflns_number_total 3416 _reflns_number_gt 3174 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0419P)^2^+0.8530P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3416 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.0951 _refine_ls_wR_factor_gt 0.0932 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C20 C 0.28916(8) 1.12936(5) 0.47056(3) 0.0265(2) Uani 0.549(2) 1 d P A 1 H20A H 0.1759 1.0937 0.4749 0.040 Uiso 0.549(2) 1 calc PR A 1 H20B H 0.3422 1.1011 0.4278 0.040 Uiso 0.549(2) 1 calc PR A 1 H20C H 0.2696 1.2062 0.4643 0.040 Uiso 0.549(2) 1 calc PR A 1 C21 C 0.93573(8) 1.16604(5) 0.61503(3) 0.0312(2) Uani 0.549(2) 1 d P A 1 H21A H 1.0014 1.1439 0.6614 0.047 Uiso 0.549(2) 1 calc PR A 1 H21B H 0.9417 1.2437 0.6103 0.047 Uiso 0.549(2) 1 calc PR A 1 H21C H 0.9880 1.1326 0.5738 0.047 Uiso 0.549(2) 1 calc PR A 1 Cl1 Cl 0.28916(8) 1.12936(5) 0.47056(3) 0.0265(2) Uani 0.451(2) 1 d P A 2 Cl2 Cl 0.93573(8) 1.16604(5) 0.61503(3) 0.0312(2) Uani 0.451(2) 1 d P A 2 O1 O 0.65894(15) 1.19196(9) 0.49265(6) 0.0316(3) Uani 1 1 d . . . C9 C 0.60089(17) 1.07910(11) 0.83787(7) 0.0200(3) Uani 1 1 d . . . H9 H 0.5990 1.1436 0.8106 0.024 Uiso 1 1 calc R . . C2 C 0.72203(18) 1.12788(11) 0.61423(8) 0.0220(3) Uani 1 1 d . . . C3 C 0.66312(18) 1.07928(11) 0.67286(7) 0.0210(3) Uani 1 1 d . A . H3 H 0.7420 1.0700 0.7161 0.025 Uiso 1 1 calc R . . C1 C 0.60624(19) 1.14647(11) 0.54608(7) 0.0234(3) Uani 1 1 d . A . C6 C 0.42409(19) 1.10754(11) 0.54600(7) 0.0229(3) Uani 1 1 d . . . C13 C 0.52355(18) 0.89478(11) 0.84791(8) 0.0228(3) Uani 1 1 d . . . H13 H 0.4656 0.8325 0.8281 0.027 Uiso 1 1 calc R . . C5 C 0.36866(18) 1.05745(11) 0.60471(7) 0.0216(3) Uani 1 1 d . A . H5 H 0.2503 1.0322 0.6019 0.026 Uiso 1 1 calc R . . C15 C 0.21027(18) 0.85664(11) 0.66833(7) 0.0219(3) Uani 1 1 d . A . H15 H 0.2912 0.8443 0.6328 0.026 Uiso 1 1 calc R . . C7 C 0.42160(17) 0.98952(11) 0.73138(7) 0.0196(3) Uani 1 1 d . A . C17 C -0.07070(18) 0.81709(11) 0.71484(8) 0.0219(3) Uani 1 1 d . A . C8 C 0.51876(17) 0.98845(11) 0.80592(7) 0.0192(3) Uani 1 1 d . . . C12 C 0.61180(18) 0.89203(12) 0.91790(8) 0.0250(3) Uani 1 1 d . . . H12 H 0.6169 0.8271 0.9448 0.030 Uiso 1 1 calc R . . C11 C 0.69338(17) 0.98273(12) 0.94976(7) 0.0229(3) Uani 1 1 d . . . C4 C 0.48326(17) 1.04067(11) 0.67203(7) 0.0197(3) Uani 1 1 d . . . C18 C -0.02928(18) 0.89157(11) 0.77087(7) 0.0225(3) Uani 1 1 d . . . H18 H -0.1112 0.9045 0.8059 0.027 Uiso 1 1 calc R . . C14 C 0.25131(17) 0.93089(11) 0.72433(7) 0.0201(3) Uani 1 1 d . . . C10 C 0.68531(17) 1.07648(11) 0.90883(7) 0.0218(3) Uani 1 1 d . . . H10 H 0.7383 1.1395 0.9297 0.026 Uiso 1 1 calc R . . C19 C 0.12895(18) 0.94664(11) 0.77599(7) 0.0217(3) Uani 1 1 d . A . H19 H 0.1553 0.9959 0.8151 0.026 Uiso 1 1 calc R . . C16 C 0.05187(18) 0.80079(11) 0.66425(8) 0.0237(3) Uani 1 1 d . . . H16 H 0.0266 0.7502 0.6260 0.028 Uiso 1 1 calc R A . C22 C -0.24195(19) 0.75614(12) 0.71028(9) 0.0280(3) Uani 1 1 d . . . H22A H -0.2445 0.7041 0.6702 0.042 Uiso 1 1 calc R A . H22B H -0.3412 0.8058 0.7008 0.042 Uiso 1 1 calc R . . H22C H -0.2516 0.7189 0.7569 0.042 Uiso 1 1 calc R . . C23 C 0.7812(2) 0.97882(14) 1.02741(8) 0.0308(3) Uani 1 1 d . . . H23A H 0.6954 0.9551 1.0607 0.046 Uiso 1 1 calc R . . H23B H 0.8246 1.0500 1.0421 0.046 Uiso 1 1 calc R . . H23C H 0.8807 0.9288 1.0300 0.046 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 C20 0.0351(4) 0.0252(3) 0.0182(3) 0.0015(2) -0.0026(2) 0.0043(2) C21 0.0310(4) 0.0340(4) 0.0303(4) 0.0000(3) 0.0117(3) -0.0061(3) Cl1 0.0351(4) 0.0252(3) 0.0182(3) 0.0015(2) -0.0026(2) 0.0043(2) Cl2 0.0310(4) 0.0340(4) 0.0303(4) 0.0000(3) 0.0117(3) -0.0061(3) O1 0.0443(6) 0.0291(6) 0.0226(5) 0.0038(4) 0.0097(5) -0.0034(5) C9 0.0187(6) 0.0204(7) 0.0216(7) 0.0021(5) 0.0050(5) 0.0012(5) C2 0.0220(7) 0.0201(7) 0.0247(7) -0.0029(5) 0.0057(5) -0.0006(5) C3 0.0217(7) 0.0213(7) 0.0200(6) -0.0011(5) 0.0023(5) 0.0017(5) C1 0.0330(8) 0.0180(7) 0.0200(7) -0.0008(5) 0.0071(6) 0.0023(6) C6 0.0292(7) 0.0197(7) 0.0197(7) -0.0019(5) 0.0013(5) 0.0049(6) C13 0.0211(7) 0.0230(7) 0.0242(7) 0.0013(5) 0.0027(5) -0.0027(5) C5 0.0215(7) 0.0214(7) 0.0220(7) -0.0009(5) 0.0018(5) 0.0017(5) C15 0.0210(7) 0.0251(7) 0.0198(7) 0.0000(5) 0.0027(5) 0.0033(5) C7 0.0197(6) 0.0193(6) 0.0199(6) -0.0009(5) 0.0024(5) 0.0028(5) C17 0.0201(7) 0.0211(7) 0.0240(7) 0.0042(5) -0.0009(5) 0.0012(5) C8 0.0155(6) 0.0237(7) 0.0187(6) 0.0011(5) 0.0039(5) 0.0012(5) C12 0.0237(7) 0.0266(7) 0.0247(7) 0.0072(6) 0.0019(5) -0.0017(6) C11 0.0164(6) 0.0330(8) 0.0195(7) 0.0017(6) 0.0029(5) -0.0005(6) C4 0.0198(6) 0.0202(6) 0.0195(6) -0.0006(5) 0.0032(5) 0.0028(5) C18 0.0205(7) 0.0258(7) 0.0215(7) 0.0024(5) 0.0035(5) 0.0019(5) C14 0.0195(6) 0.0217(7) 0.0187(6) 0.0027(5) 0.0002(5) 0.0007(5) C10 0.0179(6) 0.0253(7) 0.0227(7) -0.0036(5) 0.0040(5) -0.0017(5) C19 0.0227(7) 0.0238(7) 0.0185(6) -0.0008(5) 0.0016(5) -0.0002(5) C16 0.0245(7) 0.0233(7) 0.0226(7) -0.0025(5) -0.0005(5) 0.0010(6) C22 0.0234(7) 0.0274(8) 0.0330(8) 0.0008(6) 0.0012(6) -0.0031(6) C23 0.0251(7) 0.0456(9) 0.0214(7) 0.0042(6) 0.0004(6) -0.0046(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 C20 C6 1.6569(15) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C2 1.6912(15) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? O1 C1 1.2313(17) . ? C9 C10 1.3886(19) . ? C9 C8 1.3968(19) . ? C9 H9 0.9500 . ? C2 C3 1.3469(19) . ? C2 C1 1.470(2) . ? C3 C4 1.4483(19) . ? C3 H3 0.9500 . ? C1 C6 1.467(2) . ? C6 C5 1.346(2) . ? C13 C12 1.384(2) . ? C13 C8 1.4018(19) . ? C13 H13 0.9500 . ? C5 C4 1.4500(18) . ? C5 H5 0.9500 . ? C15 C16 1.388(2) . ? C15 C14 1.3959(19) . ? C15 H15 0.9500 . ? C7 C4 1.3811(19) . ? C7 C14 1.4826(19) . ? C7 C8 1.4833(18) . ? C17 C16 1.391(2) . ? C17 C18 1.399(2) . ? C17 C22 1.5042(19) . ? C12 C11 1.395(2) . ? C12 H12 0.9500 . ? C11 C10 1.392(2) . ? C11 C23 1.5075(19) . ? C18 C19 1.3815(19) . ? C18 H18 0.9500 . ? C14 C19 1.4027(19) . ? C10 H10 0.9500 . ? C19 H19 0.9500 . ? C16 H16 0.9500 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C20 H20A 109.5 . . ? C6 C20 H20B 109.5 . . ? C6 C20 H20C 109.5 . . ? C2 C21 H21A 109.5 . . ? C2 C21 H21B 109.5 . . ? C2 C21 H21C 109.5 . . ? C10 C9 C8 121.11(12) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C3 C2 C1 121.82(13) . . ? C3 C2 C21 121.03(11) . . ? C1 C2 C21 117.12(10) . . ? C2 C3 C4 122.04(13) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? O1 C1 C6 122.28(13) . . ? O1 C1 C2 122.05(13) . . ? C6 C1 C2 115.67(12) . . ? C5 C6 C1 121.60(13) . . ? C5 C6 C20 121.56(12) . . ? C1 C6 C20 116.84(10) . . ? C12 C13 C8 120.69(13) . . ? C12 C13 H13 119.7 . . ? C8 C13 H13 119.7 . . ? C6 C5 C4 122.32(13) . . ? C6 C5 H5 118.8 . . ? C4 C5 H5 118.8 . . ? C16 C15 C14 120.38(13) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C4 C7 C14 121.54(12) . . ? C4 C7 C8 123.26(12) . . ? C14 C7 C8 115.20(11) . . ? C16 C17 C18 117.89(13) . . ? C16 C17 C22 121.39(13) . . ? C18 C17 C22 120.72(13) . . ? C9 C8 C13 117.87(12) . . ? C9 C8 C7 122.50(12) . . ? C13 C8 C7 119.57(12) . . ? C13 C12 C11 121.31(13) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C10 C11 C12 118.09(12) . . ? C10 C11 C23 121.67(13) . . ? C12 C11 C23 120.20(13) . . ? C7 C4 C3 122.69(12) . . ? C7 C4 C5 120.77(12) . . ? C3 C4 C5 116.54(12) . . ? C19 C18 C17 120.99(13) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C15 C14 C19 118.19(13) . . ? C15 C14 C7 121.63(12) . . ? C19 C14 C7 120.15(12) . . ? C9 C10 C11 120.89(13) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C18 C19 C14 120.93(13) . . ? C18 C19 H19 119.5 . . ? C14 C19 H19 119.5 . . ? C15 C16 C17 121.61(13) . . ? C15 C16 H16 119.2 . . ? C17 C16 H16 119.2 . . ? C17 C22 H22A 109.5 . . ? C17 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C17 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C11 C23 H23A 109.5 . . ? C11 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C11 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.396 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.041