#------------------------------------------------------------------------------
#$Date: 2020-05-21 07:56:55 +0300 (Thu, 21 May 2020) $
#$Revision: 252239 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/21/2022125.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_2022125
loop_
_publ_author_name
'Mroz, Damian'
'Wang, Ruimin'
'Englert, Ulli'
'Dronskowski, Richard'
_publ_section_title
;
 Can we trust the experiment? Anisotropic displacement parameters in
 1-(halomethyl)-3-nitrobenzene (halogen = Cl or Br)
;
_journal_coeditor_code           SK3749
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229620006221
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C7 H6 Br N O2'
_chemical_formula_moiety         'C7 H6 Br N O2'
_chemical_formula_sum            'C7 H6 Br N O2'
_chemical_formula_weight         216.04
_chemical_name_systematic
;
1-(Bromomethyl)-3-nitrobenzene
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     other
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 112.626(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1412(5)
_cell_length_b                   4.4763(2)
_cell_length_c                   15.0876(6)
_cell_measurement_reflns_used    3178
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      38.06
_cell_measurement_theta_min      1.81
_cell_volume                     756.87(6)
_computing_cell_refinement
;
RECIPE in X-AREA (Stoe & Cie, 2017)
;
_computing_data_collection
;
PLATINUS in X-AREA (Stoe & Cie, 2017)
;
_computing_data_reduction
;
INTEGRATE and LANA in X-AREA (Stoe & Cie, 2017)
;
_computing_publication_material
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 Pilatus200K
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1653
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            37127
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.997
_diffrn_reflns_theta_min         1.817
_diffrn_source                   'Genix Mo'
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    5.374
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[LANA (Blessing, 1995; Koziskova et al., 2016)
in X-AREA (Stoe & Cie, 2017)]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.896
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.932
_refine_diff_density_min         -0.599
_refine_ls_extinction_coef       0.0022(6)
_refine_ls_extinction_expression Fc*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         3332
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0368
_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)+(0.0200P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0749
_reflns_number_gt                2062
_reflns_number_total             3332
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sk3749sup1.cif
_cod_data_source_block           2a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2022125
_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   0.371
_shelx_estimated_absorpt_t_max   0.814
loop_
_space_group_symop_operation_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 -0.04496(2) 0.11089(6) 0.10366(2) 0.02885(8) Uani d 1 . .
O O1 0.41819(18) -0.2481(5) 0.51406(13) 0.0338(5) Uani d 1 . .
O O2 0.29226(18) 0.1116(5) 0.49388(13) 0.0357(4) Uani d 1 . .
N N1 0.3460(2) -0.0654(5) 0.46357(15) 0.0261(5) Uani d 1 . .
C C1 0.1097(2) 0.3165(6) 0.1373(2) 0.0290(6) Uani d 1 . .
H H1A 0.123722 0.359321 0.078099 0.035 Uiso calc 1 . .
H H1B 0.107971 0.509042 0.169032 0.035 Uiso calc 1 . .
C C2 0.2085(2) 0.1268(6) 0.20295(16) 0.0215(4) Uani d 1 . .
C C3 0.2311(2) 0.1160(6) 0.30100(16) 0.0235(4) Uani d 1 . .
H H3 0.183524 0.227637 0.326488 0.028 Uiso calc 1 . .
C C4 0.3232(2) -0.0588(5) 0.35992(17) 0.0208(5) Uani d 1 . .
C C5 0.3949(2) -0.2282(5) 0.32711(17) 0.0227(5) Uani d 1 . .
H H5 0.457244 -0.348818 0.369636 0.027 Uiso calc 1 . .
C C6 0.3725(2) -0.2158(6) 0.22947(17) 0.0225(5) Uani d 1 . .
H H6 0.420784 -0.327335 0.204678 0.027 Uiso calc 1 . .
C C7 0.2798(2) -0.0412(5) 0.16797(17) 0.0220(5) Uani d 1 . .
H H7 0.264822 -0.036348 0.101386 0.026 Uiso calc 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 N1 O1 . . 123.8(2) ?
O2 N1 C4 . . 118.2(2) ?
O1 N1 C4 . . 117.9(2) ?
C2 C1 Br1 . . 110.34(17) ?
C2 C1 H1A . . 109.6 ?
Br1 C1 H1A . . 109.6 ?
C2 C1 H1B . . 109.6 ?
Br1 C1 H1B . . 109.6 ?
H1A C1 H1B . . 108.1 ?
C7 C2 C3 . . 119.0(2) ?
C7 C2 C1 . . 120.9(2) ?
C3 C2 C1 . . 120.2(2) ?
C4 C3 C2 . . 118.9(2) ?
C4 C3 H3 . . 120.5 ?
C2 C3 H3 . . 120.5 ?
C3 C4 C5 . . 123.3(2) ?
C3 C4 N1 . . 118.0(2) ?
C5 C4 N1 . . 118.7(2) ?
C4 C5 C6 . . 117.6(2) ?
C4 C5 H5 . . 121.2 ?
C6 C5 H5 . . 121.2 ?
C7 C6 C5 . . 120.5(2) ?
C7 C6 H6 . . 119.8 ?
C5 C6 H6 . . 119.8 ?
C6 C7 C2 . . 120.7(2) ?
C6 C7 H7 . . 119.6 ?
C2 C7 H7 . . 119.6 ?
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
Br1 C1 . 1.974(3) ?
O1 N1 . 1.226(3) ?
O2 N1 . 1.222(3) ?
N1 C4 . 1.480(3) ?
C1 C2 . 1.493(3) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 C7 . 1.394(3) ?
C2 C3 . 1.398(3) ?
C3 C4 . 1.374(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.381(3) ?
C5 C6 . 1.392(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.391(3) ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Br1 C1 C2 C7 . . . . 100.0(2) ?
Br1 C1 C2 C3 . . . . -80.1(3) ?
C7 C2 C3 C4 . . . . 0.3(4) ?
C1 C2 C3 C4 . . . . -179.5(2) ?
C2 C3 C4 C5 . . . . -0.6(4) ?
C2 C3 C4 N1 . . . . 179.6(2) ?
O2 N1 C4 C3 . . . . -8.9(3) ?
O1 N1 C4 C3 . . . . 171.3(2) ?
O2 N1 C4 C5 . . . . 171.2(2) ?
O1 N1 C4 C5 . . . . -8.5(3) ?
C3 C4 C5 C6 . . . . 0.8(4) ?
N1 C4 C5 C6 . . . . -179.3(2) ?
C4 C5 C6 C7 . . . . -0.9(4) ?
C5 C6 C7 C2 . . . . 0.7(4) ?
C3 C2 C7 C6 . . . . -0.4(4) ?
C1 C2 C7 C6 . . . . 179.4(2) ?

_cod_database_fobs_code 2022125
