data_ltp170s _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H18 Cl In O2' _chemical_formula_sum 'C18 H18 Cl In O2' _chemical_formula_weight 416.59 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' 'In' 'In' -0.7276 1.3100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 19.6727(4) _cell_length_b 7.74200(10) _cell_length_c 10.7323(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.7910(10) _cell_angle_gamma 90.00 _cell_volume 1633.80(5) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 6954 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 34.13 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.694 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 1.614 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5791 _exptl_absorpt_correction_T_max 0.8553 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12912 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 34.13 _reflns_number_total 6193 _reflns_number_gt 5804 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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. The following constraint and restraints were used in the ins file. sadi c8 c9 c8 c9a sadi in1 o1 in1 o2 in1a o1a in1a o2a sadi o2 c16 o2a c16 o1 c7 o1a c7 sadi c17 c18 c17 c18a sadi in1 cl1 in1a cl1a sadi C9 In1 C9a In1A C18 In1A C18a In1 eadp CL1A CL1 SIMU 0.02 C9 C18 C9A C18A O1 O2 O1A O2A ISOR 0.05 C9 C18 C9A C18A O1 O2 O1A O2A ; _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^)+(0.0329P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.250(15) _refine_ls_number_reflns 6193 _refine_ls_number_parameters 249 _refine_ls_number_restraints 95 _refine_ls_R_factor_all 0.0300 _refine_ls_R_factor_gt 0.0268 _refine_ls_wR_factor_ref 0.0637 _refine_ls_wR_factor_gt 0.0621 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.003 _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 In1 In 0.149427(10) 0.97881(3) 0.666068(14) 0.01581(8) Uani 0.7120(16) 1 d PD A 1 C9 C 0.1208(3) 0.7607(6) 0.5535(7) 0.0131(11) Uani 0.7120(16) 1 d PDU A 1 H9A H 0.1538 0.7457 0.4865 0.016 Uiso 0.7120(16) 1 calc PR A 1 H9B H 0.1217 0.6550 0.6054 0.016 Uiso 0.7120(16) 1 calc PR A 1 C18 C 0.1839(4) 1.2383(9) 0.7129(10) 0.0171(17) Uani 0.7120(16) 1 d PDU A 1 H18A H 0.1872 1.3095 0.6366 0.020 Uiso 0.7120(16) 1 calc PR A 1 H18B H 0.1520 1.2948 0.7696 0.020 Uiso 0.7120(16) 1 calc PR A 1 Cl1 Cl 0.1539(3) 0.8490(3) 0.8837(6) 0.0198(5) Uani 0.7120(16) 1 d PD A 1 O1 O 0.0275(3) 1.0215(10) 0.6368(8) 0.0322(19) Uani 0.7120(16) 1 d PDU A 1 O2 O 0.2717(2) 0.9664(6) 0.6567(4) 0.0184(8) Uani 0.7120(16) 1 d PDU A 1 In1A In 0.15448(3) 1.02004(10) 0.60830(7) 0.0190(2) Uani 0.2880(16) 1 d PD A 2 C9A C 0.1199(10) 0.7682(19) 0.562(3) 0.034(5) Uani 0.2880(16) 1 d PDU A 2 H9A1 H 0.1522 0.7109 0.5068 0.040 Uiso 0.2880(16) 1 calc PR A 2 H9A2 H 0.1163 0.6977 0.6388 0.040 Uiso 0.2880(16) 1 calc PR A 2 C18A C 0.1812(9) 1.228(2) 0.727(3) 0.013(3) Uani 0.2880(16) 1 d PDU A 2 H18C H 0.1749 1.3378 0.6810 0.016 Uiso 0.2880(16) 1 calc PR A 2 H18D H 0.1502 1.2295 0.7983 0.016 Uiso 0.2880(16) 1 calc PR A 2 Cl1A Cl 0.1464(7) 1.1479(7) 0.3906(15) 0.0198(5) Uani 0.2880(16) 1 d PD A 2 O1A O 0.0321(6) 1.000(2) 0.6493(13) 0.0117(18) Uani 0.2880(16) 1 d PDU A 2 O2A O 0.2774(5) 0.9901(16) 0.6268(8) 0.0183(19) Uani 0.2880(16) 1 d PDU A 2 C1 C -0.11007(11) 1.0245(3) 0.60551(19) 0.0185(3) Uani 1 1 d . . . H1 H -0.0898 1.0936 0.6697 0.022 Uiso 1 1 calc R . . C2 C -0.17985(11) 1.0346(3) 0.5803(2) 0.0209(4) Uani 1 1 d . . . H2 H -0.2071 1.1114 0.6264 0.025 Uiso 1 1 calc R . . C3 C -0.20945(10) 0.9316(3) 0.48736(19) 0.0206(4) Uani 1 1 d . . . H3 H -0.2570 0.9388 0.4697 0.025 Uiso 1 1 calc R . . C4 C -0.16997(11) 0.8184(3) 0.42026(19) 0.0215(4) Uani 1 1 d . . . H4 H -0.1905 0.7473 0.3576 0.026 Uiso 1 1 calc R . . C5 C -0.10009(10) 0.8092(3) 0.44494(18) 0.0193(3) Uani 1 1 d . . . H5 H -0.0730 0.7318 0.3990 0.023 Uiso 1 1 calc R . . C6 C -0.06978(10) 0.9134(2) 0.53689(17) 0.0163(3) Uani 1 1 d . A . C7 C 0.00453(10) 0.9101(2) 0.56453(17) 0.0173(3) Uani 1 1 d D . . C8 C 0.04966(10) 0.7865(3) 0.49607(17) 0.0187(3) Uani 1 1 d D A . H8A H 0.0541 0.8290 0.4097 0.022 Uiso 1 1 calc R B 1 H8B H 0.0268 0.6727 0.4912 0.022 Uiso 1 1 calc R B 1 C10 C 0.41369(11) 0.9744(3) 0.6717(2) 0.0194(3) Uani 1 1 d . . . H10 H 0.3934 0.9035 0.6086 0.023 Uiso 1 1 calc R . . C11 C 0.48294(11) 0.9667(3) 0.6955(2) 0.0214(4) Uani 1 1 d . . . H11 H 0.5101 0.8895 0.6495 0.026 Uiso 1 1 calc R . . H13 H 0.4963 1.2607 0.9120 0.026 Uiso 1 1 d R . . C12 C 0.51321(10) 1.0718(3) 0.78693(19) 0.0206(4) Uani 1 1 d . . . H12 H 0.5609 1.0665 0.8033 0.025 Uiso 1 1 calc R . . C13 C 0.47338(11) 1.1839(3) 0.85381(18) 0.0219(4) Uani 1 1 d . . . C14 C 0.40384(10) 1.1921(3) 0.83182(18) 0.0194(3) Uani 1 1 d . . . H14 H 0.3770 1.2690 0.8786 0.023 Uiso 1 1 calc R . . C15 C 0.37317(10) 1.0862(2) 0.74004(16) 0.0158(3) Uani 1 1 d . A . C16 C 0.29849(11) 1.0852(3) 0.71578(17) 0.0173(3) Uani 1 1 d D . . C17 C 0.25401(10) 1.2168(2) 0.77707(17) 0.0180(3) Uani 1 1 d D A . H17A H 0.2776 1.3298 0.7777 0.022 Uiso 1 1 calc R C 1 H17B H 0.2479 1.1822 0.8648 0.022 Uiso 1 1 calc R C 1 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 In1 0.01231(6) 0.01700(8) 0.01798(18) -0.00200(14) -0.00198(5) -0.00082(13) C9 0.015(2) 0.015(2) 0.0098(16) 0.0000(14) -0.0013(15) -0.0003(17) C18 0.018(2) 0.019(2) 0.015(3) 0.0013(17) -0.0007(19) -0.0026(15) Cl1 0.0184(12) 0.0231(2) 0.0180(7) 0.0017(4) -0.0013(7) 0.0002(4) O1 0.0213(19) 0.026(3) 0.048(3) -0.020(3) -0.0162(17) 0.0074(16) O2 0.0149(13) 0.0182(15) 0.0223(19) -0.0044(13) 0.0030(12) -0.0034(11) In1A 0.0169(2) 0.0200(3) 0.0199(5) -0.0015(3) -0.00221(17) -0.0008(2) C9A 0.026(8) 0.038(9) 0.037(9) -0.012(6) 0.009(6) 0.000(7) C18A 0.019(5) 0.013(5) 0.008(5) 0.004(3) 0.005(3) 0.001(4) Cl1A 0.0184(12) 0.0231(2) 0.0180(7) 0.0017(4) -0.0013(7) 0.0002(4) O1A 0.013(4) 0.009(3) 0.012(3) 0.000(2) -0.001(3) 0.005(3) O2A 0.016(3) 0.027(4) 0.013(4) -0.006(3) 0.004(3) -0.012(2) C1 0.0194(9) 0.0170(8) 0.0189(8) -0.0008(7) 0.0010(6) -0.0012(7) C2 0.0191(10) 0.0203(9) 0.0234(9) -0.0008(7) 0.0020(7) 0.0004(8) C3 0.0172(9) 0.0214(9) 0.0232(8) 0.0043(7) -0.0010(7) -0.0020(7) C4 0.0180(9) 0.0238(9) 0.0224(9) -0.0016(7) -0.0036(7) -0.0042(7) C5 0.0184(9) 0.0212(9) 0.0184(8) -0.0031(6) 0.0001(6) -0.0013(7) C6 0.0162(8) 0.0160(8) 0.0165(7) 0.0006(6) -0.0015(6) -0.0011(6) C7 0.0188(9) 0.0165(8) 0.0167(7) -0.0004(6) -0.0002(6) -0.0006(7) C8 0.0173(9) 0.0213(9) 0.0175(8) -0.0039(6) 0.0009(6) -0.0017(7) C10 0.0198(10) 0.0175(8) 0.0209(8) -0.0012(7) 0.0011(6) -0.0021(7) C11 0.0188(9) 0.0216(9) 0.0240(9) 0.0000(7) 0.0032(7) 0.0005(8) C12 0.0162(9) 0.0221(9) 0.0235(9) 0.0027(7) -0.0002(7) -0.0040(7) C13 0.0214(10) 0.0234(9) 0.0206(8) -0.0008(7) -0.0021(7) -0.0037(7) C14 0.0190(9) 0.0215(9) 0.0176(8) -0.0019(6) -0.0006(6) -0.0026(7) C15 0.0184(8) 0.0136(8) 0.0155(7) 0.0016(6) 0.0015(6) -0.0024(7) C16 0.0180(9) 0.0155(8) 0.0180(8) 0.0006(7) -0.0025(6) -0.0015(7) C17 0.0175(9) 0.0185(8) 0.0179(8) -0.0027(6) 0.0009(6) -0.0018(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 In1 C9 2.141(6) . ? In1 C18 2.174(6) . ? In1 O2 2.413(5) . ? In1 O1 2.431(7) . ? In1 Cl1 2.542(6) . ? C9 C8 1.525(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C18 C17 1.532(6) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? O1 C7 1.236(6) . ? O2 C16 1.227(5) . ? In1A C18A 2.111(15) . ? In1A C9A 2.118(14) . ? In1A O2A 2.431(11) . ? In1A O1A 2.467(11) . ? In1A Cl1A 2.538(15) . ? C9A C8 1.542(14) . ? C9A H9A1 0.9900 . ? C9A H9A2 0.9900 . ? C18A C17 1.516(14) . ? C18A H18C 0.9900 . ? C18A H18D 0.9900 . ? O1A C7 1.254(12) . ? O2A C16 1.266(10) . ? C1 C2 1.393(3) . ? C1 C6 1.395(3) . ? C1 H1 0.9500 . ? C2 C3 1.390(3) . ? C2 H2 0.9500 . ? C3 C4 1.387(3) . ? C3 H3 0.9500 . ? C4 C5 1.394(3) . ? C4 H4 0.9500 . ? C5 C6 1.394(2) . ? C5 H5 0.9500 . ? C6 C7 1.483(3) . ? C7 C8 1.512(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C10 C11 1.380(3) . ? C10 C15 1.399(3) . ? C10 H10 0.9500 . ? C11 C12 1.394(3) . ? C11 H11 0.9500 . ? C12 C13 1.385(3) . ? C12 H12 0.9500 . ? C13 C14 1.382(3) . ? C13 H13 0.9639 . ? C14 C15 1.403(3) . ? C14 H14 0.9500 . ? C15 C16 1.484(3) . ? C16 C17 1.508(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? 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 C9 In1 C18 159.0(3) . . ? C9 In1 O2 101.0(2) . . ? C18 In1 O2 75.1(2) . . ? C9 In1 O1 78.1(2) . . ? C18 In1 O1 101.7(2) . . ? O2 In1 O1 168.7(3) . . ? C9 In1 Cl1 102.0(2) . . ? C18 In1 Cl1 98.7(3) . . ? O2 In1 Cl1 90.96(16) . . ? O1 In1 Cl1 100.3(2) . . ? C8 C9 In1 110.3(3) . . ? C8 C9 H9A 109.6 . . ? In1 C9 H9A 109.6 . . ? C8 C9 H9B 109.6 . . ? In1 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C17 C18 In1 105.9(4) . . ? C17 C18 H18A 110.6 . . ? In1 C18 H18A 110.6 . . ? C17 C18 H18B 110.6 . . ? In1 C18 H18B 110.6 . . ? H18A C18 H18B 108.7 . . ? C7 O1 In1 109.1(4) . . ? C16 O2 In1 111.2(3) . . ? C18A In1A C9A 156.2(11) . . ? C18A In1A O2A 78.2(6) . . ? C9A In1A O2A 104.0(6) . . ? C18A In1A O1A 99.6(7) . . ? C9A In1A O1A 71.0(8) . . ? O2A In1A O1A 162.5(5) . . ? C18A In1A Cl1A 105.5(8) . . ? C9A In1A Cl1A 97.7(7) . . ? O2A In1A Cl1A 98.4(4) . . ? O1A In1A Cl1A 98.9(5) . . ? C8 C9A In1A 107.4(8) . . ? C8 C9A H9A1 110.2 . . ? In1A C9A H9A1 110.2 . . ? C8 C9A H9A2 110.2 . . ? In1A C9A H9A2 110.2 . . ? H9A1 C9A H9A2 108.5 . . ? C17 C18A In1A 112.6(10) . . ? C17 C18A H18C 109.1 . . ? In1A C18A H18C 109.1 . . ? C17 C18A H18D 109.1 . . ? In1A C18A H18D 109.1 . . ? H18C C18A H18D 107.8 . . ? C7 O1A In1A 107.9(7) . . ? C16 O2A In1A 107.9(7) . . ? C2 C1 C6 120.29(18) . . ? C2 C1 H1 119.9 . . ? C6 C1 H1 119.9 . . ? C3 C2 C1 119.70(19) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C4 C3 C2 120.38(19) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 119.90(18) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 120.17(19) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C1 119.54(18) . . ? C5 C6 C7 121.94(17) . . ? C1 C6 C7 118.53(16) . . ? O1 C7 O1A 10.6(12) . . ? O1 C7 C6 116.9(4) . . ? O1A C7 C6 122.5(6) . . ? O1 C7 C8 122.5(4) . . ? O1A C7 C8 117.1(6) . . ? C6 C7 C8 120.27(16) . . ? C7 C8 C9 115.6(3) . . ? C7 C8 C9A 111.5(9) . . ? C9 C8 C9A 4.2(13) . . ? C7 C8 H8A 108.4 . . ? C9 C8 H8A 108.4 . . ? C9A C8 H8A 111.0 . . ? C7 C8 H8B 108.4 . . ? C9 C8 H8B 108.4 . . ? C9A C8 H8B 110.0 . . ? H8A C8 H8B 107.4 . . ? C11 C10 C15 120.36(19) . . ? C11 C10 H10 119.8 . . ? C15 C10 H10 119.8 . . ? C10 C11 C12 120.2(2) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 119.63(19) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C14 C13 C12 120.87(18) . . ? C14 C13 H13 121.5 . . ? C12 C13 H13 117.5 . . ? C13 C14 C15 119.64(19) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C10 C15 C14 119.31(19) . . ? C10 C15 C16 118.82(17) . . ? C14 C15 C16 121.84(18) . . ? O2 C16 O2A 17.9(5) . . ? O2 C16 C15 120.1(3) . . ? O2A C16 C15 115.8(5) . . ? O2 C16 C17 119.1(3) . . ? O2A C16 C17 122.8(6) . . ? C15 C16 C17 120.34(16) . . ? C16 C17 C18A 116.1(8) . . ? C16 C17 C18 113.8(4) . . ? C18A C17 C18 6.9(16) . . ? C16 C17 H17A 108.8 . . ? C18A C17 H17A 112.9 . . ? C18 C17 H17A 108.8 . . ? C16 C17 H17B 108.8 . . ? C18A C17 H17B 102.0 . . ? C18 C17 H17B 108.8 . . ? H17A C17 H17B 107.7 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 34.13 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.776 _refine_diff_density_min -0.356 _refine_diff_density_rms 0.073