#------------------------------------------------------------------------------ #$Date: 2022-02-07 14:35:59 +0200 (Mon, 07 Feb 2022) $ #$Revision: 272835 $ #$URL: file:///home/coder/svn-repositories/cod/cif/8/10/45/8104547.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_8104547 loop_ _publ_author_name 'Manana, Pholani' 'Hosten, Eric C.' 'Betz, Richard' _publ_section_title ; Redetermination of the crystal structure of 3-bromonitrobenzene at 200 K, C6H4BrNO2 -- temperature effects on cell constants ; _journal_issue 6 _journal_name_full 'Zeitschrift f\"ur Kristallographie - New Crystal Structures' _journal_page_first 1131 _journal_page_last 1133 _journal_paper_doi 10.1515/ncrs-2021-0226 _journal_volume 236 _journal_year 2021 _chemical_formula_moiety 'C14 H13 N O5' _chemical_formula_sum 'C14 H13 N O5' _chemical_formula_weight 275.25 _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXTL _cell_angle_alpha 90.00 _cell_angle_beta 94.827(8) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 4.6967(7) _cell_length_b 10.7175(16) _cell_length_c 12.945(2) _cell_measurement_reflns_used 3450 _cell_measurement_temperature 223(2) _cell_measurement_theta_max 21.47 _cell_measurement_theta_min 2.47 _cell_volume 649.30(17) _computing_cell_refinement 'Bruker SAINT [1]' _computing_data_collection 'Bruker APEX2 [1]' _computing_data_reduction 'Bruker SAINT [1]' _computing_molecular_graphics 'OLEX2 [4]' _computing_publication_material 'Bruker SHELXTL [2]' _computing_structure_refinement 'SHELXL-2014/7 [3]' _computing_structure_solution 'Bruker SHELXTL [2]' _diffrn_ambient_temperature 223(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'PHOTON 100 CMOS' _diffrn_measurement_method '\f and \w scans' _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 0.1374 _diffrn_reflns_av_sigmaI/netI 0.0758 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 26931 _diffrn_reflns_theta_full 28.38 _diffrn_reflns_theta_max 28.38 _diffrn_reflns_theta_min 2.47 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_T_max 0.9946 _exptl_absorpt_correction_T_min 0.9850 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker SADABS' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Plate _exptl_crystal_F_000 288 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.297 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.045 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 182 _refine_ls_number_reflns 3254 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.013 _refine_ls_R_factor_all 0.1393 _refine_ls_R_factor_gt 0.0577 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0373P)^2^+0.3888P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1038 _refine_ls_wR_factor_ref 0.1302 _reflns_number_gt 1835 _reflns_number_total 3254 _reflns_threshold_expression >2sigma(I) _cod_data_source_file suppl_j_ncrs-2021-0247_suppl.cif _cod_data_source_block A6289-a _cod_original_sg_symbol_H-M P2(1) _cod_database_code 8104547 _publcif_info_exptl_table_max_cols 4 _publcif_info_exptl_table_use_headnotes n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' 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 C1 C 0.1748(6) 0.0642(3) 0.4571(2) 0.0320(7) Uani 1 1 d . . . O1 O 0.2163(4) 0.1571(2) 0.51261(16) 0.0406(5) Uani 1 1 d . . . C2 C -0.0446(7) 0.0647(3) 0.3685(2) 0.0344(7) Uani 1 1 d . . . C3 C -0.2081(6) 0.1703(3) 0.3418(2) 0.0401(8) Uani 1 1 d . . . H3 H -0.1774 0.2444 0.3801 0.048 Uiso 1 1 calc R . . C4 C -0.4142(7) 0.1666(4) 0.2598(3) 0.0491(9) Uani 1 1 d . . . H4 H -0.5247 0.2379 0.2426 0.059 Uiso 1 1 calc R . . C5 C -0.4597(8) 0.0588(4) 0.2025(3) 0.0532(10) Uani 1 1 d . . . H5 H -0.6013 0.0576 0.1466 0.064 Uiso 1 1 calc R . . C6 C -0.3004(8) -0.0470(4) 0.2259(3) 0.0487(9) Uani 1 1 d . . . H6 H -0.3307 -0.1204 0.1867 0.058 Uiso 1 1 calc R . . C7 C -0.0941(6) -0.0423(3) 0.3090(2) 0.0375(8) Uani 1 1 d . . . O2 O 0.0594(5) -0.1498(2) 0.32907(18) 0.0441(6) Uani 1 1 d . . . C8 C 0.2634(7) -0.1500(3) 0.4085(3) 0.0417(8) Uani 1 1 d . . . H8 H 0.3667 -0.2243 0.4213 0.050 Uiso 1 1 calc R . . C9 C 0.3316(6) -0.0519(3) 0.4714(2) 0.0326(7) Uani 1 1 d . . . C10 C 0.5677(7) -0.0726(3) 0.5499(3) 0.0368(8) Uani 1 1 d . . . H10 H 0.6522 -0.1522 0.5534 0.044 Uiso 1 1 calc R . . N1 N 0.6678(6) 0.0101(3) 0.6143(2) 0.0397(7) Uani 1 1 d . . . O3 O 0.9037(5) -0.0459(2) 0.67441(19) 0.0482(6) Uani 1 1 d . . . C11 C 1.0344(7) 0.0452(3) 0.7422(2) 0.0410(8) Uani 1 1 d . . . H11A H 1.0473 0.1242 0.7047 0.049 Uiso 1 1 calc R . . H11B H 1.2291 0.0185 0.7651 0.049 Uiso 1 1 calc R . . C12 C 0.8707(8) 0.0653(4) 0.8346(3) 0.0517(9) Uani 1 1 d . . . O4 O 0.6764(6) 0.0028(3) 0.8604(2) 0.0822(10) Uani 1 1 d . . . O5 O 0.9754(7) 0.1624(3) 0.88836(19) 0.0763(9) Uani 1 1 d . . . C13 C 0.8423(15) 0.1892(6) 0.9839(4) 0.129(3) Uani 1 1 d . . . H13A H 0.6413 0.1638 0.9753 0.155 Uiso 1 1 calc R . . H13B H 0.9369 0.1397 1.0404 0.155 Uiso 1 1 calc R . . C14 C 0.8570(19) 0.3090(6) 1.0096(5) 0.158(3) Uani 1 1 d . . . H14A H 1.0552 0.3325 1.0258 0.237 Uiso 1 1 calc R . . H14B H 0.7513 0.3231 1.0698 0.237 Uiso 1 1 calc R . . H14C H 0.7752 0.3591 0.9521 0.237 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 C1 0.0292(16) 0.0287(17) 0.0391(18) 0.0025(16) 0.0095(14) -0.0033(14) O1 0.0444(13) 0.0307(12) 0.0464(12) -0.0042(12) 0.0020(10) -0.0008(11) C2 0.0319(17) 0.0352(18) 0.0372(17) 0.0025(16) 0.0097(14) -0.0047(14) C3 0.0337(17) 0.0401(19) 0.0474(18) 0.0028(17) 0.0086(15) -0.0013(16) C4 0.0403(19) 0.056(2) 0.051(2) 0.006(2) 0.0044(16) 0.0046(19) C5 0.044(2) 0.072(3) 0.042(2) 0.007(2) -0.0020(17) -0.009(2) C6 0.056(2) 0.050(2) 0.0399(19) -0.0031(18) 0.0022(17) -0.011(2) C7 0.0359(18) 0.0383(19) 0.0388(18) 0.0017(17) 0.0061(15) -0.0036(16) O2 0.0508(14) 0.0351(13) 0.0451(14) -0.0056(11) -0.0043(12) -0.0034(12) C8 0.045(2) 0.0349(19) 0.045(2) -0.0014(17) 0.0032(17) 0.0005(17) C9 0.0333(17) 0.0301(17) 0.0349(16) 0.0028(16) 0.0059(14) -0.0024(15) C10 0.0378(18) 0.0250(18) 0.048(2) -0.0009(15) 0.0049(15) -0.0013(15) N1 0.0360(15) 0.0371(15) 0.0452(16) 0.0041(14) -0.0015(13) 0.0031(13) O3 0.0433(13) 0.0390(13) 0.0591(16) 0.0006(12) -0.0135(12) 0.0036(11) C11 0.0365(18) 0.044(2) 0.0419(19) 0.0003(16) -0.0003(15) -0.0019(15) C12 0.046(2) 0.060(2) 0.050(2) 0.011(2) 0.0043(17) 0.0101(19) O4 0.0493(16) 0.126(3) 0.0729(19) 0.0276(18) 0.0127(15) -0.0151(17) O5 0.125(3) 0.0570(17) 0.0520(15) -0.0046(16) 0.0379(16) 0.0017(19) C13 0.224(8) 0.105(5) 0.069(3) -0.008(3) 0.080(4) 0.022(5) C14 0.290(10) 0.080(5) 0.120(5) -0.033(4) 0.119(6) -0.027(5) 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' 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 O1 C1 C9 124.3(3) . . O1 C1 C2 121.0(3) . . C9 C1 C2 114.7(3) . . C7 C2 C3 118.0(3) . . C7 C2 C1 120.0(3) . . C3 C2 C1 122.0(3) . . C4 C3 C2 120.3(3) . . C4 C3 H3 119.9 . . C2 C3 H3 119.9 . . C3 C4 C5 120.4(4) . . C3 C4 H4 119.8 . . C5 C4 H4 119.8 . . C6 C5 C4 120.9(3) . . C6 C5 H5 119.5 . . C4 C5 H5 119.5 . . C5 C6 C7 118.1(4) . . C5 C6 H6 120.9 . . C7 C6 H6 120.9 . . O2 C7 C6 116.0(3) . . O2 C7 C2 121.8(3) . . C6 C7 C2 122.2(3) . . C8 O2 C7 118.4(3) . . O2 C8 C9 125.3(3) . . O2 C8 H8 117.4 . . C9 C8 H8 117.4 . . C8 C9 C1 119.9(3) . . C8 C9 C10 115.4(3) . . C1 C9 C10 124.7(3) . . N1 C10 C9 124.4(3) . . N1 C10 H10 117.8 . . C9 C10 H10 117.8 . . C10 N1 O3 106.8(3) . . C11 O3 N1 108.8(2) . . O3 C11 C12 111.7(3) . . O3 C11 H11A 109.3 . . C12 C11 H11A 109.3 . . O3 C11 H11B 109.3 . . C12 C11 H11B 109.3 . . H11A C11 H11B 107.9 . . O4 C12 O5 123.4(4) . . O4 C12 C11 126.6(4) . . O5 C12 C11 110.0(3) . . C12 O5 C13 115.7(4) . . C14 C13 O5 112.7(5) . . C14 C13 H13A 109.0 . . O5 C13 H13A 109.0 . . C14 C13 H13B 109.0 . . O5 C13 H13B 109.0 . . H13A C13 H13B 107.8 . . C13 C14 H14A 109.5 . . C13 C14 H14B 109.5 . . H14A C14 H14B 109.5 . . C13 C14 H14C 109.5 . . H14A C14 H14C 109.5 . . H14B C14 H14C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 O1 1.234(4) . C1 C9 1.450(4) . C1 C2 1.476(4) . C2 C7 1.390(4) . C2 C3 1.394(4) . C3 C4 1.376(4) . C3 H3 0.9400 . C4 C5 1.379(6) . C4 H4 0.9400 . C5 C6 1.379(5) . C5 H5 0.9400 . C6 C7 1.386(4) . C6 H6 0.9400 . C7 O2 1.372(4) . O2 C8 1.345(4) . C8 C9 1.352(4) . C8 H8 0.9400 . C9 C10 1.456(4) . C10 N1 1.279(4) . C10 H10 0.9400 . N1 O3 1.431(3) . O3 C11 1.417(4) . C11 C12 1.492(5) . C11 H11A 0.9800 . C11 H11B 0.9800 . C12 O4 1.202(5) . C12 O5 1.323(5) . O5 C13 1.460(5) . C13 C14 1.327(8) . C13 H13A 0.9800 . C13 H13B 0.9800 . C14 H14A 0.9700 . C14 H14B 0.9700 . C14 H14C 0.9700 . loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C10 H10 O1 0.94 2.32 3.195(4) 155.0 2_646 C11 H11B O4 0.98 2.35 3.296(4) 161.7 1_655 C8 H8 O1 0.94 2.43 3.297(4) 153.4 2_646 C11 H11A O2 0.98 2.50 3.415(4) 154.4 2_656 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 O1 C1 C2 C7 -177.9(3) . . . . C9 C1 C2 C7 2.3(4) . . . . O1 C1 C2 C3 1.9(4) . . . . C9 C1 C2 C3 -177.9(3) . . . . C7 C2 C3 C4 0.9(4) . . . . C1 C2 C3 C4 -178.9(3) . . . . C2 C3 C4 C5 -0.6(5) . . . . C3 C4 C5 C6 -0.1(5) . . . . C4 C5 C6 C7 0.3(5) . . . . C5 C6 C7 O2 -179.8(3) . . . . C5 C6 C7 C2 0.1(5) . . . . C3 C2 C7 O2 179.2(3) . . . . C1 C2 C7 O2 -1.0(4) . . . . C3 C2 C7 C6 -0.7(4) . . . . C1 C2 C7 C6 179.1(3) . . . . C6 C7 O2 C8 179.6(3) . . . . C2 C7 O2 C8 -0.3(4) . . . . C7 O2 C8 C9 0.0(5) . . . . O2 C8 C9 C1 1.5(5) . . . . O2 C8 C9 C10 -177.7(3) . . . . O1 C1 C9 C8 177.7(3) . . . . C2 C1 C9 C8 -2.6(4) . . . . O1 C1 C9 C10 -3.1(5) . . . . C2 C1 C9 C10 176.6(3) . . . . C8 C9 C10 N1 178.0(3) . . . . C1 C9 C10 N1 -1.3(5) . . . . C9 C10 N1 O3 -177.6(3) . . . . C10 N1 O3 C11 175.9(3) . . . . N1 O3 C11 C12 78.7(3) . . . . O3 C11 C12 O4 10.5(5) . . . . O3 C11 C12 O5 -171.3(3) . . . . O4 C12 O5 C13 0.9(6) . . . . C11 C12 O5 C13 -177.4(4) . . . . C12 O5 C13 C14 -152.1(7) . . . . loop_ _publcif_info_datablock.id _publcif_info_datablock.publ_exptl _publcif_info_datablock.publ_geom _publcif_info_datablock.structure {aec403e4-80c3-4c73-ae3e-6c873263516c} y y y loop_ _publcif_info_exptl_table_extra_item sin_theta_over_lambda_max loop_ _publcif_info_tables.block_id _publcif_info_tables.reference_item {aec403e4-80c3-4c73-ae3e-6c873263516c} '_publcif_info_datablock.publ_exptl' {aec403e4-80c3-4c73-ae3e-6c873263516c} '_geom_hbond_atom_site_label_D' loop_ _publcif_info_cif.paper_type EX