#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/73/2207354.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_2207354 loop_ _publ_author_name 'Huang, Wei' 'Zhao, Pei-Liang' 'Xie, Chang' 'Zhou, Zhong-Zhen' 'Yang, Guang-Fu' _publ_section_title ; 2-(Dibromomethyl)-4H-chromen-4-one ; _journal_coeditor_code SU6237 _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3948 _journal_page_last o3949 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C10 H6 Br2 O2' _chemical_formula_moiety 'C10 H6 Br2 O2' _chemical_formula_sum 'C10 H6 Br2 O2' _chemical_formula_weight 317.97 _chemical_name_systematic ; 2-(Dibromomethyl)chromen-4-one ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 96.884(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.2343(14) _cell_length_b 10.3445(18) _cell_length_c 12.047(2) _cell_measurement_reflns_used 2048 _cell_measurement_temperature 292(2) _cell_measurement_theta_max 25.14 _cell_measurement_theta_min 2.60 _cell_volume 1018.8(3) _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_collection 'SMART (Bruker, 1997)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Bruker, 2001)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 292(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker SMART 4K CCD area-detector' _diffrn_measurement_method '\f and \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 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 5018 _diffrn_reflns_theta_full 25.05 _diffrn_reflns_theta_max 25.05 _diffrn_reflns_theta_min 2.60 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 7.925 _exptl_absorpt_correction_T_max 0.453 _exptl_absorpt_correction_T_min 0.179 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour pink _exptl_crystal_density_diffrn 2.073 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 608 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.562 _refine_diff_density_min -0.468 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.130 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 127 _refine_ls_number_reflns 1802 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.130 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0348 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0485P)^2^+1.7251P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1017 _refine_ls_wR_factor_ref 0.1057 _reflns_number_gt 1496 _reflns_number_total 1802 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file su6237.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _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: '_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_cell_volume 1018.7(3) _cod_database_code 2207354 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_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 Br1 -0.10007(7) 0.85625(5) -0.08048(5) 0.0491(2) Uani d . 1 Br Br2 0.04440(8) 0.71887(7) -0.28348(5) 0.0644(2) Uani d . 1 Br C1 0.3022(6) 0.6042(4) 0.0471(4) 0.0343(10) Uani d . 1 C C2 0.2568(6) 0.4892(5) 0.0930(4) 0.0437(12) Uani d . 1 C H2 0.1551 0.4524 0.0702 0.052 Uiso calc R 1 H C3 0.3660(8) 0.4301(5) 0.1735(5) 0.0558(15) Uani d . 1 C H3 0.3369 0.3529 0.2055 0.067 Uiso calc R 1 H C4 0.5161(6) 0.4832(5) 0.2069(4) 0.0460(13) Uani d . 1 C H4 0.5882 0.4421 0.2610 0.055 Uiso calc R 1 H C5 0.5603(6) 0.5970(5) 0.1605(4) 0.0416(12) Uani d . 1 C H5 0.6626 0.6321 0.1840 0.050 Uiso calc R 1 H C6 0.4581(5) 0.6598(4) 0.0811(4) 0.0342(10) Uani d . 1 C C7 0.4971(5) 0.7845(4) 0.0326(4) 0.0346(10) Uani d . 1 C C8 0.3713(7) 0.8379(5) -0.0469(4) 0.0438(12) Uani d . 1 C H8 0.3888 0.9172 -0.0799 0.053 Uiso calc R 1 H C9 0.2288(6) 0.7760(5) -0.0748(4) 0.0358(11) Uani d . 1 C C10 0.0947(7) 0.8300(5) -0.1536(4) 0.0462(13) Uani d . 1 C H10 0.1300 0.9141 -0.1794 0.055 Uiso calc R 1 H O1 0.1931(4) 0.6599(3) -0.0318(3) 0.0386(8) Uani d . 1 O O2 0.6280(5) 0.8394(4) 0.0597(3) 0.0522(10) Uani d . 1 O 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 Br1 0.0454(3) 0.0483(3) 0.0507(4) 0.0002(2) -0.0056(2) -0.0017(2) Br2 0.0662(4) 0.0905(5) 0.0352(3) -0.0166(3) 0.0002(3) -0.0060(3) C1 0.039(3) 0.034(2) 0.030(2) -0.003(2) 0.004(2) -0.001(2) C2 0.040(3) 0.042(3) 0.048(3) -0.009(2) 0.000(2) 0.007(2) C3 0.088(5) 0.039(3) 0.041(3) 0.002(3) 0.012(3) 0.009(2) C4 0.040(3) 0.054(3) 0.041(3) 0.005(3) -0.007(2) 0.005(3) C5 0.038(3) 0.048(3) 0.038(3) -0.001(2) 0.000(2) -0.004(2) C6 0.032(2) 0.039(3) 0.032(2) -0.001(2) 0.003(2) -0.006(2) C7 0.023(2) 0.039(3) 0.041(3) -0.007(2) 0.003(2) -0.007(2) C8 0.061(3) 0.032(3) 0.038(3) -0.009(2) 0.007(2) 0.003(2) C9 0.035(2) 0.038(2) 0.034(3) -0.008(2) 0.001(2) 0.003(2) C10 0.055(3) 0.043(3) 0.039(3) -0.014(2) 0.000(2) 0.007(2) O1 0.0361(18) 0.0364(18) 0.0414(19) -0.0103(15) -0.0033(15) 0.0068(15) O2 0.051(2) 0.048(2) 0.057(2) -0.0094(18) 0.0032(19) -0.0017(18) 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' Br Br -0.2901 2.4595 '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 O1 C1 C2 117.2(4) O1 C1 C6 122.0(4) C2 C1 C6 120.8(5) C1 C2 C3 118.5(5) C1 C2 H2 120.8 C3 C2 H2 120.8 C4 C3 C2 121.1(5) C4 C3 H3 119.4 C2 C3 H3 119.4 C3 C4 C5 120.0(5) C3 C4 H4 120.0 C5 C4 H4 120.0 C6 C5 C4 121.7(5) C6 C5 H5 119.2 C4 C5 H5 119.2 C5 C6 C1 118.0(4) C5 C6 C7 123.6(4) C1 C6 C7 118.3(4) O2 C7 C8 122.7(4) O2 C7 C6 121.9(4) C8 C7 C6 115.4(4) C9 C8 C7 121.5(4) C9 C8 H8 119.2 C7 C8 H8 119.2 C8 C9 O1 123.3(4) C8 C9 C10 123.0(4) O1 C9 C10 113.7(4) C9 C10 Br1 110.9(3) C9 C10 Br2 111.4(4) Br1 C10 Br2 109.9(3) C9 C10 H10 108.2 Br1 C10 H10 108.2 Br2 C10 H10 108.2 C9 O1 C1 119.3(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C10 1.939(6) Br2 C10 1.946(5) C1 O1 1.355(6) C1 C2 1.382(7) C1 C6 1.422(6) C2 C3 1.384(8) C2 H2 0.9300 C3 C4 1.368(8) C3 H3 0.9300 C4 C5 1.370(8) C4 H4 0.9300 C5 C6 1.361(7) C5 H5 0.9300 C6 C7 1.467(7) C7 O2 1.227(6) C7 C8 1.435(7) C8 C9 1.344(7) C8 H8 0.9300 C9 O1 1.354(5) C9 C10 1.477(7) C10 H10 0.9800 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 C8 H8 O2 3_675 0.93 2.54 3.342(6) 145.3 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 O1 C1 C2 C3 179.8(5) C6 C1 C2 C3 0.6(7) C1 C2 C3 C4 -0.4(8) C2 C3 C4 C5 0.1(8) C3 C4 C5 C6 -0.1(8) C4 C5 C6 C1 0.2(7) C4 C5 C6 C7 177.3(5) O1 C1 C6 C5 -179.7(4) C2 C1 C6 C5 -0.5(7) O1 C1 C6 C7 3.1(7) C2 C1 C6 C7 -177.7(4) C5 C6 C7 O2 1.5(8) C1 C6 C7 O2 178.5(4) C5 C6 C7 C8 -177.7(5) C1 C6 C7 C8 -0.7(6) O2 C7 C8 C9 -179.8(5) C6 C7 C8 C9 -0.6(7) C7 C8 C9 O1 -0.5(8) C7 C8 C9 C10 178.0(5) C8 C9 C10 Br1 -118.2(5) O1 C9 C10 Br1 60.4(5) C8 C9 C10 Br2 119.1(5) O1 C9 C10 Br2 -62.2(5) C8 C9 O1 C1 2.9(7) C10 C9 O1 C1 -175.7(4) C2 C1 O1 C9 176.6(4) C6 C1 O1 C9 -4.2(6) _cod_database_fobs_code 2207354 _journal_paper_doi 10.1107/S1600536805035166