#------------------------------------------------------------------------------ #$Date: 2016-02-20 03:06:23 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/25/2202523.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_2202523 loop_ _publ_author_name 'Xue-Mei Li' 'Hua-You Hu' 'Jian-Hua Xu' 'Shu-Sheng Zhang' 'Hoong-Kun Fun' _publ_section_title 2a,5a-Dichloro-4-methyl-1-methylene-2-phenyl-2a,5a-dihydrocyclobuta[c]pyrrole-3,5-dione _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1822 _journal_page_last o1823 _journal_paper_doi 10.1107/S1600536803024103 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C14 H11 Cl2 N O2' _chemical_formula_moiety 'C14 H11 Cl2 N O2' _chemical_formula_sum 'C14 H11 Cl2 N O2' _chemical_formula_weight 296.14 _chemical_melting_point 407.5(5) _chemical_name_systematic ;2a,5a-Dichloro-4-methyl-1-methylene-2-phenyl-2a,5a-dihydrocyclobuta[c]pyrrole- 3,5-dione ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 106.1670(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 14.8302(11) _cell_length_b 7.3973(5) _cell_length_c 25.3885(18) _cell_measurement_reflns_used 3429 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.10 _cell_measurement_theta_min 2.88 _cell_volume 2675.1(3) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990) ; _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Siemens SMART CCD area-detector' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_number 8171 _diffrn_reflns_theta_full 28.33 _diffrn_reflns_theta_max 28.33 _diffrn_reflns_theta_min 2.86 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.481 _exptl_absorpt_correction_T_max 0.9270 _exptl_absorpt_correction_T_min 0.8020 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1216 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.309 _refine_diff_density_min -0.270 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.204 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 205 _refine_ls_number_reflns 3302 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.204 _refine_ls_R_factor_all 0.0809 _refine_ls_R_factor_gt 0.0633 _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^)+(0.0479P)^2^+3.9853P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1317 _refine_ls_wR_factor_ref 0.1379 _reflns_number_gt 2656 _reflns_number_total 3302 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ci6293.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_chemical_melting_point' value '407-408 K' was changed to '407.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '407-408 K' was changed to '407.5(5)' - the average value was taken and precision was estimated. '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2202523 _cod_database_fobs_code 2202523 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' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cl1 -0.01248(4) 0.95649(9) 0.07205(3) 0.0386(2) Uani d . 1 . . Cl Cl2 0.10127(6) 0.92538(11) 0.20482(3) 0.0495(2) Uani d . 1 . . Cl O1 0.09626(15) 0.6853(3) 0.01726(8) 0.0524(6) Uani d . 1 . . O O2 0.27917(15) 0.7240(3) 0.19346(9) 0.0571(6) Uani d . 1 . . O N1 0.20372(15) 0.6917(3) 0.10169(10) 0.0355(5) Uani d . 1 . . N C1 0.11558(18) 0.7078(4) 0.06601(11) 0.0333(6) Uani d . 1 . . C C2 0.04696(17) 0.7578(3) 0.09887(10) 0.0277(5) Uani d . 1 . . C C3 0.10893(18) 0.7510(4) 0.15935(10) 0.0314(6) Uani d . 1 . . C C4 0.20898(19) 0.7243(4) 0.15627(12) 0.0368(6) Uani d . 1 . . C C5 0.2864(2) 0.6441(4) 0.08401(15) 0.0481(8) Uani d . 1 . . C H5A 0.2889 0.7187 0.0535 0.072 Uiso calc R 1 . . H H5B 0.2827 0.5194 0.0732 0.072 Uiso calc R 1 . . H H5C 0.3420 0.6631 0.1137 0.072 Uiso calc R 1 . . H C6 0.06019(18) 0.5739(4) 0.16548(11) 0.0338(6) Uani d . 1 . . C C7 -0.01225(19) 0.5920(4) 0.10977(11) 0.0314(6) Uani d . 1 . . C C8 -0.11163(18) 0.6327(3) 0.11099(11) 0.0303(5) Uani d . 1 . . C C9 -0.1848(2) 0.6099(4) 0.06379(12) 0.0390(7) Uani d . 1 . . C C10 -0.2768(2) 0.6453(5) 0.06369(14) 0.0457(8) Uani d . 1 . . C C11 -0.2962(2) 0.7040(4) 0.11067(14) 0.0452(7) Uani d . 1 . . C C12 -0.2244(2) 0.7273(5) 0.15780(14) 0.0456(7) Uani d . 1 . . C C13 -0.1328(2) 0.6916(4) 0.15785(12) 0.0405(7) Uani d . 1 . . C C14 0.0794(3) 0.4499(5) 0.20380(15) 0.0510(8) Uani d . 1 . . C H14B 0.040(3) 0.344(5) 0.1978(14) 0.059(10) Uiso d . 1 . . H H13 -0.085(2) 0.708(4) 0.1898(12) 0.038(8) Uiso d . 1 . . H H7 -0.0099(18) 0.497(4) 0.0871(11) 0.027(7) Uiso d . 1 . . H H9 -0.172(2) 0.568(5) 0.0330(14) 0.051(9) Uiso d . 1 . . H H10 -0.320(2) 0.625(5) 0.0327(15) 0.062(11) Uiso d . 1 . . H H11 -0.358(2) 0.736(4) 0.1114(12) 0.045(9) Uiso d . 1 . . H H12 -0.237(2) 0.768(5) 0.1862(14) 0.053(10) Uiso d . 1 . . H H14A 0.132(2) 0.466(5) 0.2363(15) 0.055(10) Uiso d . 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 0.0284(3) 0.0391(4) 0.0477(4) 0.0070(3) 0.0093(3) 0.0131(3) Cl2 0.0708(5) 0.0432(4) 0.0358(4) 0.0038(4) 0.0172(3) -0.0105(3) O1 0.0493(12) 0.0805(17) 0.0320(11) 0.0001(12) 0.0193(9) -0.0085(11) O2 0.0337(11) 0.0698(16) 0.0558(14) -0.0002(11) -0.0074(10) -0.0026(12) N1 0.0267(11) 0.0378(13) 0.0436(13) 0.0043(9) 0.0123(9) -0.0009(10) C1 0.0311(13) 0.0367(15) 0.0356(15) 0.0013(11) 0.0153(11) -0.0015(12) C2 0.0260(12) 0.0312(13) 0.0259(12) 0.0064(10) 0.0076(9) 0.0004(10) C3 0.0342(13) 0.0334(14) 0.0253(12) 0.0054(11) 0.0063(10) -0.0037(11) C4 0.0318(14) 0.0325(14) 0.0436(16) 0.0012(11) 0.0061(12) 0.0008(12) C5 0.0324(14) 0.0426(17) 0.077(2) 0.0069(13) 0.0285(15) 0.0027(16) C6 0.0339(13) 0.0368(15) 0.0326(14) 0.0085(11) 0.0123(11) 0.0032(11) C7 0.0368(14) 0.0272(13) 0.0333(14) 0.0016(11) 0.0147(11) -0.0036(11) C8 0.0328(13) 0.0261(13) 0.0333(14) -0.0042(10) 0.0117(11) 0.0008(10) C9 0.0443(16) 0.0396(16) 0.0329(15) -0.0038(13) 0.0105(12) -0.0050(12) C10 0.0315(15) 0.0517(19) 0.0467(18) -0.0085(13) -0.0012(13) -0.0013(15) C11 0.0333(15) 0.0456(18) 0.059(2) -0.0035(13) 0.0169(14) 0.0005(15) C12 0.0416(16) 0.055(2) 0.0451(18) 0.0004(14) 0.0204(14) -0.0040(15) C13 0.0329(14) 0.0560(19) 0.0328(15) -0.0022(13) 0.0096(12) -0.0051(13) C14 0.058(2) 0.046(2) 0.0484(19) 0.0125(17) 0.0140(16) 0.0129(16) 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 N1 C4 115.0(2) y C1 N1 C5 123.0(2) y C4 N1 C5 122.0(2) y O1 C1 N1 125.3(2) ? O1 C1 C2 126.2(2) ? N1 C1 C2 108.5(2) ? C1 C2 C3 103.34(19) ? C1 C2 C7 113.3(2) ? C3 C2 C7 90.37(19) ? C1 C2 Cl1 109.28(18) ? C3 C2 Cl1 120.40(18) ? C7 C2 Cl1 118.44(17) ? C4 C3 C6 113.0(2) ? C4 C3 C2 105.7(2) ? C6 C3 C2 87.82(19) ? C4 C3 Cl2 111.84(19) ? C6 C3 Cl2 116.41(19) ? C2 C3 Cl2 119.79(18) ? O2 C4 N1 125.7(3) ? O2 C4 C3 127.4(3) ? N1 C4 C3 106.8(2) ? N1 C5 H5A 109.5 ? N1 C5 H5B 109.5 ? H5A C5 H5B 109.5 ? N1 C5 H5C 109.5 ? H5A C5 H5C 109.5 ? H5B C5 H5C 109.5 ? C14 C6 C3 131.8(3) ? C14 C6 C7 134.6(3) ? C3 C6 C7 93.5(2) ? C8 C7 C6 115.9(2) ? C8 C7 C2 116.2(2) ? C6 C7 C2 87.03(19) ? C8 C7 H7 111.9(16) ? C6 C7 H7 112.0(17) ? C2 C7 H7 111.5(17) ? C13 C8 C9 118.2(3) ? C13 C8 C7 122.4(2) ? C9 C8 C7 119.4(2) ? C8 C9 C10 120.7(3) ? C8 C9 H9 119(2) ? C10 C9 H9 120(2) ? C11 C10 C9 120.1(3) ? C11 C10 H10 124(2) ? C9 C10 H10 116(2) ? C12 C11 C10 119.8(3) ? C12 C11 H11 118.0(19) ? C10 C11 H11 122.1(19) ? C11 C12 C13 120.0(3) ? C11 C12 H12 119(2) ? C13 C12 H12 121(2) ? C8 C13 C12 121.2(3) ? C8 C13 H13 119.3(19) ? C12 C13 H13 119.6(19) ? C6 C14 H14B 117(2) ? C6 C14 H14A 120(2) ? H14B C14 H14A 123(3) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C2 . 1.751(3) y Cl2 C3 . 1.756(3) y O1 C1 . 1.202(3) y O2 C4 . 1.195(3) y N1 C1 . 1.373(3) y N1 C4 . 1.387(4) y N1 C5 . 1.462(3) y C1 C2 . 1.530(4) yes C2 C3 . 1.555(3) yes C2 C7 . 1.577(4) yes C3 C4 . 1.520(4) yes C3 C6 . 1.525(4) yes C5 H5A . 0.96 ? C5 H5B . 0.96 ? C5 H5C . 0.96 ? C6 C14 . 1.309(4) y C6 C7 . 1.525(4) y C7 C8 . 1.513(4) y C7 H7 . 0.92(3) ? C8 C13 . 1.383(4) ? C8 C9 . 1.385(4) ? C9 C10 . 1.388(4) ? C9 H9 . 0.91(4) ? C10 C11 . 1.373(5) ? C10 H10 . 0.88(3) ? C11 C12 . 1.373(4) ? C11 H11 . 0.94(3) ? C12 C13 . 1.383(4) ? C12 H12 . 0.85(4) ? C13 H13 . 0.93(3) ? C14 H14B . 0.96(4) ? C14 H14A . 0.97(4) ? 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 C5 H5C O2 1_555 0.96 2.49 2.872(4) 103 yes C5 H5B CgP 3_545 0.96 2.75 3.579(3) 145 yes 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 C4 N1 C1 O1 179.9(3) C5 N1 C1 O1 0.0(5) C4 N1 C1 C2 -0.4(3) C5 N1 C1 C2 179.7(2) O1 C1 C2 C3 175.0(3) N1 C1 C2 C3 -4.7(3) O1 C1 C2 C7 78.7(4) N1 C1 C2 C7 -101.0(2) O1 C1 C2 Cl1 -55.7(4) N1 C1 C2 Cl1 124.6(2) C1 C2 C3 C4 7.6(3) C7 C2 C3 C4 121.7(2) Cl1 C2 C3 C4 -114.6(2) C1 C2 C3 C6 -105.7(2) C7 C2 C3 C6 8.37(18) Cl1 C2 C3 C6 132.15(19) C1 C2 C3 Cl2 134.9(2) C7 C2 C3 Cl2 -111.0(2) Cl1 C2 C3 Cl2 12.7(3) C1 N1 C4 O2 -177.1(3) C5 N1 C4 O2 2.8(5) C1 N1 C4 C3 5.5(3) C5 N1 C4 C3 -174.6(2) C6 C3 C4 O2 -91.1(4) C2 C3 C4 O2 174.6(3) Cl2 C3 C4 O2 42.6(4) C6 C3 C4 N1 86.3(3) C2 C3 C4 N1 -8.1(3) Cl2 C3 C4 N1 -140.0(2) C4 C3 C6 C14 61.6(4) C2 C3 C6 C14 167.7(3) Cl2 C3 C6 C14 -69.9(4) C4 C3 C6 C7 -114.8(2) C2 C3 C6 C7 -8.67(19) Cl2 C3 C6 C7 113.7(2) C14 C6 C7 C8 74.5(4) C3 C6 C7 C8 -109.3(2) C14 C6 C7 C2 -167.7(3) C3 C6 C7 C2 8.56(19) C1 C2 C7 C8 -146.1(2) C3 C2 C7 C8 109.2(2) Cl1 C2 C7 C8 -16.2(3) C1 C2 C7 C6 96.3(2) C3 C2 C7 C6 -8.38(18) Cl1 C2 C7 C6 -133.75(19) C6 C7 C8 C13 14.7(4) C2 C7 C8 C13 -85.4(3) C6 C7 C8 C9 -165.1(3) C2 C7 C8 C9 94.8(3) C13 C8 C9 C10 -0.1(4) C7 C8 C9 C10 179.7(3) C8 C9 C10 C11 0.1(5) C9 C10 C11 C12 -0.1(5) C10 C11 C12 C13 0.0(5) C9 C8 C13 C12 -0.1(5) C7 C8 C13 C12 -179.8(3) C11 C12 C13 C8 0.1(5)