#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/25/2012528.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_2012528 loop_ _publ_author_name 'Glidewell, Christopher' 'Low, John N.' 'McWilliam, Susan A.' 'Skakle, Janet M. S.' 'Wardell, James L.' _publ_section_title ; Hydrogen bonding in C-substituted nitroanilines: sheets built from alternating Rf̱{_2^2}(12) and Rf̱{_6^6}(36) rings in 2-bromo-6-cyano-4-nitroaniline ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o100 _journal_page_last o102 _journal_paper_doi 10.1107/S0108270101021485 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C7 H4 Br N3 O2' _chemical_formula_sum 'C7 H4 Br N3 O2' _chemical_formula_weight 242.04 _chemical_name_systematic ; 2-amino-3-bromo-5-nitrobenzonitrile ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 96.138(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.2494(2) _cell_length_b 14.9094(7) _cell_length_c 13.0958(7) _cell_measurement_reflns_used 1894 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 3.13 _cell_volume 824.94(7) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD Server Software (Nonius, 1997)' _computing_data_reduction DENZO-SMN _computing_molecular_graphics 'PLATON (Spek, 2001)' _computing_publication_material 'SHELXL97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full .999 _diffrn_measured_fraction_theta_max .995 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .067 _diffrn_reflns_av_sigmaI/netI .068 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 6073 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 3.13 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 4.949 _exptl_absorpt_correction_T_max .820 _exptl_absorpt_correction_T_min .647 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO-SMN; Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.949 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 472 _exptl_crystal_size_max .25 _exptl_crystal_size_mid .07 _exptl_crystal_size_min .04 _refine_diff_density_max .54 _refine_diff_density_min -.68 _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 118 _refine_ls_number_reflns 1894 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.013 _refine_ls_R_factor_all .061 _refine_ls_R_factor_gt .037 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0309P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .074 _refine_ls_wR_factor_ref .081 _reflns_number_gt 1413 _reflns_number_total 1894 _reflns_threshold_expression I>2\s(I) _cod_data_source_file sk1529.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2012528 _cod_database_fobs_code 2012528 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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 C1 .6308(6) .3273(2) .3617(2) .0177(7) Uani d . 1 . . C N1 .8557(6) .31971(18) .44131(19) .0238(6) Uani d . 1 . . N C2 .5015(6) .2505(2) .3078(2) .0193(7) Uani d . 1 . . C Br2 .64966(7) .13636(2) .35302(2) .02578(14) Uani d . 1 . . Br C3 .2741(7) .2580(2) .2263(2) .0209(7) Uani d . 1 . . C C4 .1656(7) .3424(2) .1945(2) .0204(7) Uani d . 1 . . C N4 -.0817(6) .35126(18) .1092(2) .0236(6) Uani d . 1 . . N O41 -.1809(5) .28113(16) .06679(17) .0313(6) Uani d . 1 . . O O42 -.1848(5) .42561(16) .08419(17) .0328(6) Uani d . 1 . . O C5 .2842(7) .4196(2) .2432(2) .0206(7) Uani d . 1 . . C C6 .5128(6) .4118(2) .3261(2) .0198(7) Uani d . 1 . . C C61 .6425(6) .4918(2) .3756(2) .0232(7) Uani d . 1 . . C N61 .7567(7) .55297(19) .4168(2) .0358(7) Uani d . 1 . . N H11 .9343 .3681 .4730 .029 Uiso calc R 1 . . H H12 .9247 .2663 .4618 .029 Uiso calc R 1 . . H H3 .1907 .2059 .1916 .025 Uiso calc R 1 . . H H5 .2097 .4769 .2201 .025 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 C1 .0186(16) .0153(16) .0193(16) -.0011(12) .0023(12) -.0006(12) N1 .0293(14) .0140(14) .0258(15) -.0016(11) -.0073(11) -.0008(11) C2 .0224(16) .0136(16) .0218(17) -.0022(12) .0019(12) -.0043(13) Br2 .0325(2) .0148(2) .0284(2) .00081(13) -.00392(13) -.00073(14) C3 .0215(15) .0165(17) .0247(18) -.0053(13) .0028(12) -.0018(13) C4 .0199(16) .0228(18) .0179(16) -.0021(12) -.0012(12) -.0020(13) N4 .0234(14) .0272(17) .0197(14) -.0033(12) .0000(11) -.0015(13) O41 .0366(12) .0274(14) .0270(13) -.0080(11) -.0092(10) -.0040(11) O42 .0386(13) .0261(14) .0304(13) .0056(11) -.0119(10) -.0017(11) C5 .0216(15) .0171(16) .0230(17) -.0004(13) .0012(12) -.0029(14) C6 .0221(16) .0172(17) .0197(16) -.0037(13) .0004(12) -.0015(13) C61 .0252(17) .0201(19) .0220(17) .0014(14) -.0083(12) .0038(14) N61 .0495(18) .0192(16) .0351(17) -.0024(13) -.0115(14) -.0018(14) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -.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 _geom_angle_publ_flag N1 C1 C6 121.9(3) no N1 C1 C2 121.5(3) no C6 C1 C2 116.6(3) no C1 N1 H11 120.0 no C1 N1 H12 120.0 no H11 N1 H12 120.0 no C3 C2 C1 121.7(3) no C3 C2 Br2 120.2(2) no C1 C2 Br2 118.1(2) no C2 C3 C4 119.6(3) no C2 C3 H3 120.2 no C4 C3 H3 120.2 no C5 C4 C3 121.5(3) no C5 C4 N4 118.4(3) no C3 C4 N4 120.1(3) no O42 N4 O41 123.4(3) no O42 N4 C4 119.7(3) no O41 N4 C4 116.8(3) no C6 C5 C4 118.9(3) no C6 C5 H5 120.6 no C4 C5 H5 120.6 no C5 C6 C1 121.8(3) no C5 C6 C61 119.2(3) no C1 C6 C61 119.0(3) no N61 C61 C6 176.9(3) no 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 C1 C2 . 1.424(4) y C2 C3 . 1.365(4) y C3 C4 . 1.388(4) y C4 C5 . 1.385(4) y C5 C6 . 1.382(4) y C6 C1 . 1.416(4) y C2 Br2 . 1.888(3) y C1 N1 . 1.342(4) y C4 N4 . 1.456(4) y C6 C61 . 1.439(4) y C61 N61 . 1.140(4) y N4 O41 . 1.236(3) y N4 O42 . 1.224(3) y N1 H11 . .8800 no N1 H12 . .8800 no C3 H3 . .9500 no C5 H5 . .9500 no 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 N1 H11 N61 3_766 .88 2.19 3.019(4) 157 y N1 H12 O41 4_655 .88 2.17 2.854(3) 134 y 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 C3 C4 N4 O41 -1.5(4) y C3 C4 N4 O42 177.2(3) no C5 C4 N4 O41 179.4(3) no C5 C4 N4 O42 -1.9(4) y