#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/67/2206799.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2206799 _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _[local]_cod_cif_authors_sg_H-M 'P 21/c' loop_ _publ_author_name 'Lei Wang' 'Wen Yang' 'De-Chun Zhang' _publ_section_title ; 1,3-Bis(4-chlorophenyl)prop-2-en-1-one ; _journal_coeditor_code TK6238 _journal_issue 9 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o2820 _journal_page_last 2822 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C15 H10 Cl2 O' _chemical_formula_moiety 'C15 H10 Cl2 O' _chemical_formula_sum 'C15 H10 Cl2 O' _chemical_formula_weight 277.13 _chemical_melting_point .428E-305 _chemical_name_systematic ; 1,3-Bis(4-chlorophenyl)prop-2-en-1-one ; _symmetry_cell_setting monoclinic _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 92.908(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.325(3) _cell_length_b 14.009(2) _cell_length_c 5.8501(10) _cell_measurement_reflns_used 4017 _cell_measurement_temperature 193(2) _cell_measurement_theta_max 26.4 _cell_measurement_theta_min 3.0 _cell_volume 1254.3(4) _computing_cell_refinement CrystalClear _computing_data_collection 'CrystalClear (Rigaku, 1999)' _computing_data_reduction 'CrystalStructure (Rigaku, 2000)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 193(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method '\w and \f' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71070 _diffrn_reflns_av_R_equivalents 0.037 _diffrn_reflns_av_sigmaI/netI 0.030 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 12957 _diffrn_reflns_theta_full 26.4 _diffrn_reflns_theta_max 26.4 _diffrn_reflns_theta_min 3.0 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.500 _exptl_absorpt_correction_T_max 0.952 _exptl_absorpt_correction_T_min 0.885 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(ABSCOR; Jacobson, 1998)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.468 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 568 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.25 _refine_diff_density_min -0.27 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.15 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 164 _refine_ls_number_reflns 2549 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.15 _refine_ls_R_factor_all 0.063 _refine_ls_R_factor_gt 0.048 _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^)+(0.0351P)^2^+0.6039P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.098 _refine_ls_wR_factor_ref 0.105 _reflns_number_gt 2109 _reflns_number_total 2549 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file tk6238.cif 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' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol Cl1 0.13688(4) 0.87551(5) 0.24181(12) 0.0520(2) Uani d . 1 Cl Cl2 0.98538(4) 0.85574(5) 0.76034(11) 0.0515(2) Uani d . 1 Cl O1 0.52958(11) 0.87320(13) -0.1987(3) 0.0462(4) Uani d . 1 O C1 0.41966(14) 0.87436(14) 0.0693(4) 0.0293(5) Uani d . 1 C C2 0.39509(14) 0.90720(15) 0.2824(4) 0.0325(5) Uani d . 1 C H2 0.4385 0.9277 0.3934 0.039 Uiso calc R 1 H C3 0.30778(15) 0.90992(15) 0.3322(4) 0.0351(5) Uani d . 1 C H3 0.2908 0.9341 0.4751 0.042 Uiso calc R 1 H C4 0.24574(14) 0.87724(15) 0.1726(4) 0.0332(5) Uani d . 1 C C5 0.26815(14) 0.84412(15) -0.0390(4) 0.0344(5) Uani d . 1 C H5 0.2245 0.8222 -0.1477 0.041 Uiso calc R 1 H C6 0.35493(14) 0.84341(14) -0.0895(4) 0.0321(5) Uani d . 1 C H6 0.3710 0.8214 -0.2352 0.039 Uiso calc R 1 H C7 0.74095(13) 0.88928(14) 0.3031(3) 0.0283(5) Uani d . 1 C C8 0.82155(14) 0.92138(15) 0.2331(4) 0.0334(5) Uani d . 1 C H8 0.8247 0.9503 0.0868 0.040 Uiso calc R 1 H C9 0.89706(15) 0.91220(16) 0.3713(4) 0.0370(5) Uani d . 1 C H9 0.9514 0.9345 0.3211 0.044 Uiso calc R 1 H C10 0.89194(14) 0.87001(15) 0.5835(4) 0.0336(5) Uani d . 1 C C11 0.81306(14) 0.83811(15) 0.6594(4) 0.0331(5) Uani d . 1 C H11 0.8106 0.8093 0.8060 0.040 Uiso calc R 1 H C12 0.73804(14) 0.84827(14) 0.5214(4) 0.0306(5) Uani d . 1 C H12 0.6837 0.8273 0.5746 0.037 Uiso calc R 1 H C13 0.51247(14) 0.87384(15) 0.0047(4) 0.0332(5) Uani d . 1 C C14 0.58259(14) 0.87272(15) 0.1879(4) 0.0326(5) Uani d . 1 C H14 0.5688 0.8556 0.3391 0.039 Uiso calc R 1 H C15 0.66429(14) 0.89506(14) 0.1455(4) 0.0308(5) Uani d . 1 C H15 0.6740 0.9173 -0.0045 0.037 Uiso calc R 1 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.0340(3) 0.0621(4) 0.0605(4) 0.0071(3) 0.0075(3) 0.0001(3) Cl2 0.0373(3) 0.0677(4) 0.0482(4) -0.0036(3) -0.0093(3) 0.0080(3) O1 0.0388(9) 0.0693(12) 0.0307(9) -0.0046(8) 0.0035(7) 0.0001(8) C1 0.0326(11) 0.0260(10) 0.0291(10) -0.0005(9) 0.0000(9) 0.0035(8) C2 0.0377(12) 0.0313(11) 0.0281(11) -0.0014(9) -0.0032(9) -0.0006(9) C3 0.0439(13) 0.0316(11) 0.0299(11) 0.0062(10) 0.0037(10) 0.0001(9) C4 0.0307(11) 0.0291(11) 0.0400(12) 0.0046(9) 0.0022(10) 0.0038(9) C5 0.0345(12) 0.0325(11) 0.0354(12) -0.0003(9) -0.0051(10) -0.0023(9) C6 0.0382(12) 0.0303(11) 0.0276(11) 0.0009(9) -0.0007(9) -0.0015(9) C7 0.0322(11) 0.0245(10) 0.0286(10) 0.0026(8) 0.0038(9) -0.0003(8) C8 0.0379(12) 0.0320(11) 0.0307(11) -0.0025(10) 0.0059(10) 0.0025(9) C9 0.0341(12) 0.0400(13) 0.0373(12) -0.0054(10) 0.0057(10) 0.0025(10) C10 0.0321(11) 0.0354(12) 0.0328(11) 0.0008(9) -0.0018(9) -0.0023(9) C11 0.0379(12) 0.0326(11) 0.0288(11) -0.0006(9) 0.0014(9) 0.0002(9) C12 0.0314(11) 0.0293(11) 0.0314(11) -0.0014(9) 0.0055(9) 0.0000(9) C13 0.0364(12) 0.0309(11) 0.0320(11) -0.0026(9) -0.0013(10) 0.0017(9) C14 0.0337(12) 0.0373(12) 0.0266(11) -0.0010(9) 0.0007(9) 0.0043(9) C15 0.0355(12) 0.0279(10) 0.0292(11) 0.0026(9) 0.0029(9) 0.0022(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C4 1.737(2) y Cl2 C10 1.735(2) y O1 C13 1.231(3) y C1 C6 1.394(3) ? C1 C2 1.398(3) ? C1 C13 1.490(3) y C2 C3 1.384(3) ? C2 H2 0.9500 ? C3 C4 1.377(3) ? C3 H3 0.9500 ? C4 C5 1.382(3) ? C5 C6 1.377(3) ? C5 H5 0.9500 ? C6 H6 0.9500 ? C7 C8 1.395(3) ? C7 C12 1.403(3) ? C7 C15 1.458(3) y C8 C9 1.384(3) ? C8 H8 0.9500 ? C9 C10 1.381(3) ? C9 H9 0.9500 ? C10 C11 1.383(3) ? C11 C12 1.378(3) ? C11 H11 0.9500 ? C12 H12 0.9500 ? C13 C14 1.479(3) y C14 C15 1.326(3) y C14 H14 0.9500 ? C15 H15 0.9500 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C6 C1 C2 118.8(2) y C6 C1 C13 119.05(19) y C2 C1 C13 122.11(19) y C3 C2 C1 120.3(2) ? C3 C2 H2 119.9 ? C1 C2 H2 119.9 ? C4 C3 C2 119.31(19) ? C4 C3 H3 120.3 ? C2 C3 H3 120.3 ? C3 C4 C5 121.7(2) y C3 C4 Cl1 119.00(17) y C5 C4 Cl1 119.31(17) y C6 C5 C4 118.8(2) ? C6 C5 H5 120.6 ? C4 C5 H5 120.6 ? C5 C6 C1 121.15(19) ? C5 C6 H6 119.4 ? C1 C6 H6 119.4 ? C8 C7 C12 117.96(19) y C8 C7 C15 119.53(18) y C12 C7 C15 122.44(19) y C9 C8 C7 121.66(19) ? C9 C8 H8 119.2 ? C7 C8 H8 119.2 ? C10 C9 C8 118.8(2) ? C10 C9 H9 120.6 ? C8 C9 H9 120.6 ? C9 C10 C11 121.2(2) y C9 C10 Cl2 120.17(17) y C11 C10 Cl2 118.67(17) y C12 C11 C10 119.7(2) ? C12 C11 H11 120.2 ? C10 C11 H11 120.2 ? C11 C12 C7 120.76(19) ? C11 C12 H12 119.6 ? C7 C12 H12 119.6 ? O1 C13 C14 121.2(2) y O1 C13 C1 119.9(2) y C14 C13 C1 118.95(18) y C15 C14 C13 121.34(19) y C15 C14 H14 119.3 ? C13 C14 H14 119.3 ? C14 C15 C7 127.33(19) y C14 C15 H15 116.3 ? C7 C15 H15 116.3 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag C6 C1 C2 C3 -0.9(3) ? C13 C1 C2 C3 177.48(19) y C1 C2 C3 C4 2.0(3) ? C2 C3 C4 C5 -1.8(3) ? C2 C3 C4 Cl1 176.91(16) y C3 C4 C5 C6 0.5(3) ? Cl1 C4 C5 C6 -178.24(16) y C4 C5 C6 C1 0.7(3) ? C2 C1 C6 C5 -0.5(3) ? C13 C1 C6 C5 -178.89(19) y C12 C7 C8 C9 1.0(3) ? C15 C7 C8 C9 -176.1(2) y C7 C8 C9 C10 0.1(3) ? C8 C9 C10 C11 -0.7(3) ? C8 C9 C10 Cl2 179.14(17) y C9 C10 C11 C12 0.1(3) ? Cl2 C10 C11 C12 -179.68(16) y C10 C11 C12 C7 1.0(3) ? C8 C7 C12 C11 -1.5(3) ? C15 C7 C12 C11 175.48(19) y C6 C1 C13 O1 20.7(3) y C2 C1 C13 O1 -157.7(2) y C6 C1 C13 C14 -158.45(19) y C2 C1 C13 C14 23.2(3) y O1 C13 C14 C15 17.3(3) y C1 C13 C14 C15 -163.6(2) y C13 C14 C15 C7 -174.3(2) y C8 C7 C15 C14 -176.1(2) y C12 C7 C15 C14 6.9(3) y loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C2 H2 O1 1_556 0.95 2.81 3.613(3) 143 y C14 H14 O1 1_556 0.95 2.81 3.719(3) 160 y C12 H12 O1 1_556 0.95 2.84 3.680(3) 148 y C9 H9 Cl1 1_655 0.95 3.02 3.825(2) 144 y _cod_database_code 2206799 _journal_paper_doi 10.1107/S1600536805024566