#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/23/2232324.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_2232324
loop_
_publ_author_name
'Moreno-Fuquen, Rodolfo'
_publ_section_title
;
 4-Nitrophenyl 4-bromobenzoate
;
_journal_coeditor_code           HG5114
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3114
_journal_paper_doi               10.1107/S1600536811043923
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C13 H8 Br N O4'
_chemical_formula_moiety         'C13 H8 Br N O4'
_chemical_formula_sum            'C13 H8 Br N O4'
_chemical_formula_weight         322.11
_chemical_melting_point          431.0(10)
_chemical_name_systematic
;
4-Nitrophenyl 4-bromobenzoate
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.024(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8177(4)
_cell_length_b                   9.5279(5)
_cell_length_c                   14.9394(5)
_cell_measurement_reflns_used    5487
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.103
_cell_measurement_theta_min      2.91
_cell_volume                     1239.59(10)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       'ω 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  0.0702
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9341
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.08
_diffrn_reflns_theta_min         3.49
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.325
_exptl_absorpt_correction_T_max  0.3605
_exptl_absorpt_correction_T_min  0.2495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.545
_exptl_crystal_size_mid          0.307
_exptl_crystal_size_min          0.234
_refine_diff_density_max         0.804
_refine_diff_density_min         -0.683
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2648
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0482
_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/[σ²(Fo²)+(0.0723P)²+0.6227P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1365
_reflns_number_gt                1918
_reflns_number_total             2648
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg5114.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2232324
_cod_database_fobs_code          2232324
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_type_symbol
_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_symmetry_multiplicity
Br Br 1.07826(4) 0.25892(4) 1.01950(2) 0.0659(2) Uani d . 1 1
O O2 0.6701(3) 0.1952(3) 0.59586(16) 0.0569(6) Uani d . 1 1
C C1 0.9755(4) 0.2726(4) 0.8984(2) 0.0507(8) Uani d . 1 1
O O1 0.7563(3) 0.4159(3) 0.58276(16) 0.0606(6) Uani d . 1 1
C C4 0.8266(4) 0.2946(3) 0.7227(2) 0.0457(7) Uani d . 1 1
C C8 0.5953(4) 0.1968(4) 0.5064(2) 0.0480(7) Uani d . 1 1
C C11 0.4518(4) 0.1846(4) 0.3321(2) 0.0504(8) Uani d . 1 1
C C10 0.5615(4) 0.0861(4) 0.3623(2) 0.0552(8) Uani d . 1 1
H H10 0.5859 0.0161 0.3235 0.066 Uiso calc R 1 1
N N1 0.3778(5) 0.1834(4) 0.2373(2) 0.0694(9) Uani d . 1 1
C C7 0.7503(4) 0.3138(4) 0.6281(2) 0.0485(7) Uani d . 1 1
C C5 0.9242(4) 0.4006(4) 0.7604(3) 0.0594(9) Uani d . 1 1
H H5 0.9388 0.4796 0.7261 0.071 Uiso calc R 1 1
C C2 0.8757(4) 0.1668(4) 0.8629(2) 0.0527(8) Uani d . 1 1
H H2 0.8587 0.0893 0.8978 0.063 Uiso calc R 1 1
C C3 0.8023(4) 0.1793(3) 0.7748(2) 0.0499(8) Uani d . 1 1
H H3 0.7354 0.1090 0.7499 0.060 Uiso calc R 1 1
C C6 0.9997(5) 0.3897(4) 0.8482(2) 0.0631(10) Uani d . 1 1
H H6 1.0659 0.4603 0.8732 0.076 Uiso calc R 1 1
C C9 0.6350(4) 0.0922(3) 0.4507(2) 0.0535(8) Uani d . 1 1
H H9 0.7101 0.0268 0.4724 0.064 Uiso calc R 1 1
C C13 0.4817(4) 0.2937(4) 0.4769(2) 0.0554(8) Uani d . 1 1
H H13 0.4546 0.3616 0.5162 0.066 Uiso calc R 1 1
O O3 0.4181(5) 0.0922(4) 0.18766(19) 0.0955(11) Uani d . 1 1
C C12 0.4100(5) 0.2880(4) 0.3889(3) 0.0580(9) Uani d . 1 1
H H12 0.3340 0.3527 0.3674 0.070 Uiso calc R 1 1
O O4 0.2819(6) 0.2721(4) 0.2116(3) 0.1064(14) Uani d . 1 1
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'
Br Br -0.2901 2.4595 '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
C7 O2 C8 117.8(3)
C6 C1 C2 121.5(3)
C6 C1 Br 118.9(3)
C2 C1 Br 119.6(3)
C3 C4 C5 119.4(3)
C3 C4 C7 123.3(3)
C5 C4 C7 117.3(3)
C9 C8 C13 122.0(3)
C9 C8 O2 116.4(3)
C13 C8 O2 121.5(3)
C10 C11 C12 121.8(3)
C10 C11 N1 119.8(3)
C12 C11 N1 118.4(4)
C11 C10 C9 119.1(3)
C11 C10 H10 120.4
C9 C10 H10 120.4
O4 N1 O3 123.6(4)
O4 N1 C11 118.9(4)
O3 N1 C11 117.5(4)
O1 C7 O2 122.4(3)
O1 C7 C4 126.2(3)
O2 C7 C4 111.4(3)
C6 C5 C4 120.5(3)
C6 C5 H5 119.8
C4 C5 H5 119.8
C3 C2 C1 118.5(3)
C3 C2 H2 120.7
C1 C2 H2 120.7
C2 C3 C4 121.0(3)
C2 C3 H3 119.5
C4 C3 H3 119.5
C5 C6 C1 119.0(3)
C5 C6 H6 120.5
C1 C6 H6 120.5
C8 C9 C10 118.9(3)
C8 C9 H9 120.5
C10 C9 H9 120.5
C12 C13 C8 118.9(3)
C12 C13 H13 120.5
C8 C13 H13 120.5
C13 C12 C11 119.2(4)
C13 C12 H12 120.4
C11 C12 H12 120.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br C1 1.896(4)
O2 C7 1.379(4)
O2 C8 1.394(4)
C1 C6 1.380(5)
C1 C2 1.387(5)
O1 C7 1.192(4)
C4 C3 1.383(5)
C4 C5 1.388(5)
C4 C7 1.477(5)
C8 C9 1.378(5)
C8 C13 1.383(5)
C11 C10 1.372(5)
C11 C12 1.387(5)
C11 N1 1.465(4)
C10 C9 1.379(5)
C10 H10 0.9300
N1 O4 1.214(5)
N1 O3 1.230(5)
C5 C6 1.379(5)
C5 H5 0.9300
C2 C3 1.378(5)
C2 H2 0.9300
C3 H3 0.9300
C6 H6 0.9300
C9 H9 0.9300
C13 C12 1.367(5)
C13 H13 0.9300
C12 H12 0.9300
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
C10 H10 O4 2_645 0.93 2.69 3.543(6) 153.0
C3 H3 O3 3_656 0.93 2.60 3.335(5) 136.1
C13 H13 O3 4_566 0.93 2.67 3.460(5) 143.4
C12 H12 O1 3_666 0.93 2.50 3.237(5) 136.8
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
C7 O2 C8 C9 123.0(3)
C7 O2 C8 C13 -60.4(4)
C12 C11 C10 C9 -1.7(5)
N1 C11 C10 C9 177.2(3)
C10 C11 N1 O4 -179.4(4)
C12 C11 N1 O4 -0.4(6)
C10 C11 N1 O3 0.0(5)
C12 C11 N1 O3 178.9(4)
C8 O2 C7 O1 0.6(5)
C8 O2 C7 C4 -178.4(3)
C3 C4 C7 O1 173.0(4)
C5 C4 C7 O1 -5.4(5)
C3 C4 C7 O2 -8.0(5)
C5 C4 C7 O2 173.5(3)
C3 C4 C5 C6 1.7(6)
C7 C4 C5 C6 -179.8(4)
C6 C1 C2 C3 1.3(5)
Br C1 C2 C3 179.9(3)
C1 C2 C3 C4 -0.3(5)
C5 C4 C3 C2 -1.2(5)
C7 C4 C3 C2 -179.6(3)
C4 C5 C6 C1 -0.7(6)
C2 C1 C6 C5 -0.9(6)
Br C1 C6 C5 -179.5(3)
C13 C8 C9 C10 1.5(5)
O2 C8 C9 C10 178.1(3)
C11 C10 C9 C8 0.4(5)
C9 C8 C13 C12 -2.0(6)
O2 C8 C13 C12 -178.5(3)
C8 C13 C12 C11 0.7(6)
C10 C11 C12 C13 1.2(6)
N1 C11 C12 C13 -177.7(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5400212
