#------------------------------------------------------------------------------
#$Date: 2022-03-25 09:52:13 +0200 (Fri, 25 Mar 2022) $
#$Revision: 273969 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/48/8104855.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_8104855
loop_
_publ_author_name
'Hosten, Eric C.'
'Betz, Richard'
_publ_section_title
;
 The crystal structure of para-nitrobenzylbromide, C7H6BrNO2 -- A
 second polymorph and correction of 3D coordinates
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              443
_journal_page_last               445
_journal_paper_doi               10.1515/ncrs-2020-0564
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C7 H6 Br N O2'
_chemical_formula_sum            'C7 H6 Br N O2'
_chemical_formula_weight         216.04
_chemical_name_common            para-nitrobenzylbromide
_chemical_name_systematic        para-nitrobenzylbromide
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     SHELXS
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.7019(6)
_cell_length_b                   6.4700(9)
_cell_length_c                   25.283(4)
_cell_measurement_reflns_used    3457
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      3.22
_cell_volume                     769.14(19)
_computing_cell_refinement       'SAINT [1]'
_computing_data_collection       'APEX2 [1]'
_computing_data_reduction        'SAINT [1]'
_computing_molecular_graphics    'ORTEP3 [3], Mercury [4]'
_computing_publication_material  'SHELXL-97 [2], PLATON [5]'
_computing_structure_refinement  'SHELXL-97 [2]'
_computing_structure_solution    'SHELXS-97 [2]'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            6983
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.981
_diffrn_reflns_theta_min         3.223
_exptl_absorpt_coefficient_mu    5.288
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7657
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;                                                              
SADABS [6]                                         
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.866
_exptl_crystal_description       rod
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.056(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1854
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0294
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0359P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0649
_refine_ls_wR_factor_ref         0.0671
_reflns_Friedel_coverage         0.642
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                1583
_reflns_number_total             1854
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0564_suppl.cif
_cod_data_source_block           g
_cod_database_code               8104855
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.23357(10) 0.04014(6) 0.22432(2) 0.04408(15) Uani 1 1 d . . . . .
O1 O 0.5682(6) 0.8376(4) 0.06872(10) 0.0376(7) Uani 1 1 d . . . . .
O2 O 0.5052(6) 0.5864(4) 0.01375(10) 0.0357(7) Uani 1 1 d . . . . .
N1 N 0.6222(7) 0.6632(5) 0.05236(12) 0.0275(7) Uani 1 1 d . . . . .
C1 C 1.2296(8) 0.3067(5) 0.13533(12) 0.0243(7) Uani 1 1 d . . . . .
C2 C 1.1623(8) 0.5066(6) 0.15216(14) 0.0297(9) Uani 1 1 d . . . . .
H2 H 1.252854 0.562323 0.182576 0.036 Uiso 1 1 calc R U . . .
C3 C 0.9648(8) 0.6240(6) 0.12488(13) 0.0271(8) Uani 1 1 d . . . . .
H3 H 0.917248 0.759395 0.136447 0.033 Uiso 1 1 calc R U . . .
C4 C 0.8378(7) 0.5399(5) 0.08028(13) 0.0230(7) Uani 1 1 d . . . . .
C5 C 0.9028(8) 0.3436(6) 0.06217(13) 0.0256(8) Uani 1 1 d . . . . .
H5 H 0.814296 0.289823 0.031330 0.031 Uiso 1 1 calc R U . . .
C6 C 1.0993(8) 0.2277(5) 0.08992(13) 0.0270(8) Uani 1 1 d . . . . .
H6 H 1.146351 0.092666 0.078011 0.032 Uiso 1 1 calc R U . . .
C7 C 1.4360(8) 0.1792(6) 0.16603(13) 0.0305(8) Uani 1 1 d . . . . .
H7A H 1.588254 0.268503 0.180481 0.037 Uiso 1 1 calc R U . . .
H7B H 1.524724 0.074905 0.142606 0.037 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O2 N1 O1 123.2(3) . .
O2 N1 C4 118.2(3) . .
O1 N1 C4 118.6(3) . .
C2 C1 C6 119.3(3) . .
C2 C1 C7 120.0(3) . .
C6 C1 C7 120.7(3) . .
C3 C2 C1 120.5(3) . .
C3 C2 H2 119.7 . .
C1 C2 H2 119.7 . .
C2 C3 C4 118.6(3) . .
C2 C3 H3 120.7 . .
C4 C3 H3 120.7 . .
C5 C4 C3 122.3(3) . .
C5 C4 N1 119.4(3) . .
C3 C4 N1 118.3(3) . .
C6 C5 C4 118.6(3) . .
C6 C5 H5 120.7 . .
C4 C5 H5 120.7 . .
C5 C6 C1 120.8(3) . .
C5 C6 H6 119.6 . .
C1 C6 H6 119.6 . .
C1 C7 Br1 109.1(2) . .
C1 C7 H7A 109.9 . .
Br1 C7 H7A 109.9 . .
C1 C7 H7B 109.9 . .
Br1 C7 H7B 109.9 . .
H7A C7 H7B 108.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C7 1.971(4) .
O1 N1 1.228(4) .
O2 N1 1.226(4) .
N1 C4 1.470(4) .
C1 C2 1.398(5) .
C1 C6 1.398(5) .
C1 C7 1.491(5) .
C2 C3 1.384(5) .
C2 H2 0.9500 .
C3 C4 1.387(5) .
C3 H3 0.9500 .
C4 C5 1.384(5) .
C5 C6 1.381(5) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
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
C6 H6 O1 0.95 2.59 3.394(4) 142.4 1_645
C7 H7B O1 0.99 2.43 3.365(5) 158.0 1_645
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
C6 C1 C2 C3 1.3(5) . . . .
C7 C1 C2 C3 -178.1(3) . . . .
C1 C2 C3 C4 -0.7(5) . . . .
C2 C3 C4 C5 -0.3(5) . . . .
C2 C3 C4 N1 178.3(3) . . . .
O2 N1 C4 C5 0.4(5) . . . .
O1 N1 C4 C5 -179.5(3) . . . .
O2 N1 C4 C3 -178.2(3) . . . .
O1 N1 C4 C3 1.9(5) . . . .
C3 C4 C5 C6 0.6(5) . . . .
N1 C4 C5 C6 -177.9(3) . . . .
C4 C5 C6 C1 0.0(5) . . . .
C2 C1 C6 C5 -0.9(5) . . . .
C7 C1 C6 C5 178.4(3) . . . .
C2 C1 C7 Br1 84.5(4) . . . .
C6 C1 C7 Br1 -94.8(3) . . . .
