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#$Date: 2022-02-07 13:30:22 +0100 (lun 07 de feb de 2022) $
#$Revision: 272834 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/45/8104546.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_8104546
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 für 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         'C6 H4 Br N O2'
_chemical_formula_sum            'C6 H4 Br N O2'
_chemical_formula_weight         202.01
_chemical_name_common            meta-bromonitrobenzene
_chemical_name_systematic        3-bromonitrobenzene
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     SHELXS
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.3992(17)
_cell_length_b                   5.9311(4)
_cell_length_c                   5.2923(4)
_cell_measurement_reflns_used    1966
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.13
_cell_measurement_theta_min      2.86
_cell_volume                     671.70(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            3459
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.303
_diffrn_reflns_theta_min         1.903
_exptl_absorpt_coefficient_mu    6.048
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5179
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;                                                              
SADABS [6]                                         
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.998
_exptl_crystal_description       rod
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.504
_exptl_crystal_size_mid          0.259
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.773
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;                                                                          
Flack, H. D. (1983)                                                        
Acta Cryst. A39, 882--892.    				    
;
_refine_ls_abs_structure_Flack   0.026(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1595
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0284
_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)+(0.027200P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0708
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.954
_reflns_Friedel_fraction_max     0.897
_reflns_number_gt                1364
_reflns_number_total             1595
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;
TITL la053_a.res in Pna2(1)
    la053.res
    created by SHELXL-2018/3 at 18:17:46 on 31-May-2021
REM Old TITL la053_c in Pna2(1)
REM SHELXT solution in Pna2(1): R1 0.083, Rweak 0.006, Alpha 0.010
REM <I/s>   0.947 for   98 systematic absences,  Orientation as input
REM Flack x =  0.035 ( 0.012 ) from   484 Parsons' quotients
REM Formula found by SHELXT:  C7 O2 Br
CELL 0.71073  21.3992   5.9311   5.2923  90.000  90.000  90.000
ZERR    4.00   0.0017   0.0004   0.0004   0.000   0.000   0.000
LATT -1
SYMM -X, -Y, 1/2+Z
SYMM 1/2+X, 1/2-Y, Z
SYMM 1/2-X, 1/2+Y, 1/2+Z
SFAC C H N O BR
UNIT 24 16 4 8 4

OMIT     18   1   0

EQIV $1 x,1+y,-1+z

HTAB C5 O1_$1

ACTA NOHKL
BOND $H
CONF
FMAP 2
HTAB
L.S. 100
LIST 4
PLAN 20
SIZE 0.14 0.259 0.504
TEMP -73.140

REM WGHT 0.027200
REM WGHT 0.027200
REM WGHT 0.027200
WGHT    0.027200
FVAR       0.23429
BR1   5    0.264267    0.547255    0.089198    11.00000    0.03073    0.04528 =
         0.03410   -0.00077   -0.00680   -0.00722
O1    4    0.419072    0.364547    0.849339    11.00000    0.04241    0.03637 =
         0.03446    0.01195   -0.00338   -0.00206
O2    4    0.480540    0.651310    0.912198    11.00000    0.03438    0.04228 =
         0.03159   -0.00037   -0.00983    0.00149
N1    3    0.438392    0.554986    0.798344    11.00000    0.02680    0.02769 =
         0.02358    0.00097    0.00161    0.00658
C1    1    0.332178    0.684585    0.263281    11.00000    0.02306    0.03202 =
         0.02442   -0.00399    0.00011   -0.00081
C2    1    0.358927    0.571469    0.464367    11.00000    0.02748    0.02257 =
         0.02523    0.00156    0.00278   -0.00070
AFIX  43
H2    2    0.343943    0.428412    0.517733    11.00000   -1.20000
AFIX   0
C3    1    0.408323    0.675625    0.583952    11.00000    0.02537    0.02622 =
         0.01926    0.00209    0.00354    0.00434
C4    1    0.431311    0.884812    0.515113    11.00000    0.02463    0.03013 =
         0.02944   -0.00115   -0.00161   -0.00011
AFIX  43
H4    2    0.465486    0.951069    0.602372    11.00000   -1.20000
AFIX   0
C5    1    0.402602    0.995321    0.313071    11.00000    0.03102    0.02274 =
         0.03460    0.00361    0.00427    0.00142
AFIX  43
H5    2    0.417025    1.139877    0.262316    11.00000   -1.20000
AFIX   0
C6    1    0.353020    0.894962    0.185749    11.00000    0.02683    0.03299 =
         0.02550    0.00259    0.00185    0.00459
AFIX  43
H6    2    0.333674    0.969520    0.047468    11.00000   -1.20000
AFIX   0
HKLF 4




REM  la053_a.res in Pna2(1)
REM wR2 = 0.0708, GooF = S = 1.089, Restrained GooF = 1.089 for all data
REM R1 = 0.0284 for 1364 Fo > 4sig(Fo) and 0.0364 for all 1595 data
REM 91 parameters refined using 1 restraints

END 
;
_cod_data_source_file            suppl_j_ncrs-2021-0226_suppl.cif
_cod_data_source_block           1
_cod_database_code               8104546
_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.
;
_shelx_estimated_absorpt_t_min   0.100
_shelx_estimated_absorpt_t_max   0.485
_iucr_geom_bonds_special_details
;                                                              
Cg(1) is the centroid of carbon atoms C1--C6.               
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, 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 0.26427(2) 0.54725(8) 0.08920(17) 0.03670(16) Uani 1 1 d . . . . .
O1 O 0.41907(19) 0.3645(6) 0.8493(7) 0.0377(9) Uani 1 1 d . . . . .
O2 O 0.48054(18) 0.6513(6) 0.9122(6) 0.0361(8) Uani 1 1 d . . . . .
N1 N 0.4384(2) 0.5550(6) 0.7983(7) 0.0260(9) Uani 1 1 d . . . . .
C1 C 0.3322(2) 0.6846(7) 0.2633(9) 0.0265(10) Uani 1 1 d . . . . .
C2 C 0.3589(2) 0.5715(7) 0.4644(9) 0.0251(10) Uani 1 1 d . . . . .
H2 H 0.343943 0.428412 0.517733 0.030 Uiso 1 1 calc R U . . .
C3 C 0.40832(18) 0.6756(6) 0.5840(12) 0.0236(7) Uani 1 1 d . . . . .
C4 C 0.4313(2) 0.8848(8) 0.5151(9) 0.0281(10) Uani 1 1 d . . . . .
H4 H 0.465486 0.951069 0.602372 0.034 Uiso 1 1 calc R U . . .
C5 C 0.4026(3) 0.9953(8) 0.3131(10) 0.0295(11) Uani 1 1 d . . . . .
H5 H 0.417025 1.139877 0.262316 0.035 Uiso 1 1 calc R U . . .
C6 C 0.3530(2) 0.8950(8) 0.1857(9) 0.0284(10) Uani 1 1 d . . . . .
H6 H 0.333674 0.969520 0.047468 0.034 Uiso 1 1 calc R U . . .
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
Br1 0.0307(2) 0.0453(3) 0.0341(2) -0.0008(5) -0.0068(3) -0.0072(2)
O1 0.042(2) 0.0364(18) 0.0345(19) 0.0120(16) -0.0034(16) -0.0021(19)
O2 0.034(2) 0.0423(19) 0.0316(18) -0.0004(16) -0.0098(16) 0.0015(18)
N1 0.027(2) 0.028(2) 0.024(2) 0.0010(16) 0.0016(16) 0.0066(18)
C1 0.023(2) 0.032(2) 0.024(2) -0.0040(18) 0.0001(18) -0.001(2)
C2 0.027(2) 0.023(2) 0.025(2) 0.0016(17) 0.0028(19) -0.0007(19)
C3 0.0254(19) 0.0262(18) 0.0193(16) 0.002(3) 0.004(3) 0.0043(15)
C4 0.025(2) 0.030(2) 0.029(3) -0.0011(16) -0.0016(17) 0.000(2)
C5 0.031(3) 0.023(2) 0.035(3) 0.0036(19) 0.004(2) 0.001(2)
C6 0.027(3) 0.033(2) 0.0255(19) 0.0026(18) 0.0019(18) 0.005(2)
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O2 N1 O1 124.5(4) . .
O2 N1 C3 118.0(3) . .
O1 N1 C3 117.6(4) . .
C2 C1 C6 122.1(5) . .
C2 C1 Br1 118.8(3) . .
C6 C1 Br1 119.2(4) . .
C3 C2 C1 117.0(4) . .
C3 C2 H2 121.5 . .
C1 C2 H2 121.5 . .
C2 C3 C4 123.6(5) . .
C2 C3 N1 117.8(4) . .
C4 C3 N1 118.6(4) . .
C3 C4 C5 117.8(5) . .
C3 C4 H4 121.1 . .
C5 C4 H4 121.1 . .
C6 C5 C4 120.4(5) . .
C6 C5 H5 119.8 . .
C4 C5 H5 119.8 . .
C1 C6 C5 119.1(5) . .
C1 C6 H6 120.4 . .
C5 C6 H6 120.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.904(5) .
O1 N1 1.233(5) .
O2 N1 1.226(5) .
N1 C3 1.488(7) .
C1 C2 1.382(6) .
C1 C6 1.387(7) .
C2 C3 1.378(7) .
C2 H2 0.9500 .
C3 C4 1.384(6) .
C4 C5 1.397(7) .
C4 H4 0.9500 .
C5 C6 1.391(7) .
C5 H5 0.9500 .
C6 H6 0.9500 .
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
C5 H5 O1 0.95 2.56 3.308(6) 135.8 1_564
C1 Br1 <i>C<i>~g~(1) 1.904(5) 3.638(2) 5.514(5) 167.87(15) 3_544
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 -0.9(7) . . . .
Br1 C1 C2 C3 179.4(3) . . . .
C1 C2 C3 C4 0.8(7) . . . .
C1 C2 C3 N1 -179.1(4) . . . .
O2 N1 C3 C2 -176.9(4) . . . .
O1 N1 C3 C2 3.1(6) . . . .
O2 N1 C3 C4 3.3(6) . . . .
O1 N1 C3 C4 -176.8(4) . . . .
C2 C3 C4 C5 0.0(7) . . . .
N1 C3 C4 C5 179.9(4) . . . .
C3 C4 C5 C6 -0.6(7) . . . .
C2 C1 C6 C5 0.3(8) . . . .
Br1 C1 C6 C5 180.0(4) . . . .
C4 C5 C6 C1 0.5(8) . . . .
