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#$Date: 2023-02-09 12:31:25 +0200 (Thu, 09 Feb 2023) $
#$Revision: 280851 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/67/8106748.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.
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data_8106748
loop_
_publ_author_name
'Karczmarzyk, Zbigniew'
'Pitucha, Monika'
'Wysocki, Waldemar'
'Morawiak, Maja'
'Sobótka-Polska, Karolina'
'Urbańczyk-Lipkowska, Zofia'
_publ_section_title
;
 The crystal structure of methyl N-(4-bromophenyl)carbamate, C8H8BrNO2
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1003
_journal_page_last               1004
_journal_paper_doi               10.1515/ncrs-2017-0130
_journal_volume                  232
_journal_year                    2017
_chemical_formula_sum            'C8 H8 Br N O2'
_chemical_formula_weight         230.06
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.1313(3)
_cell_length_b                   8.5416(4)
_cell_length_c                   20.4597(7)
_cell_measurement_reflns_used    1387
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.62
_cell_measurement_theta_min      4.32
_cell_volume                     1770.53(12)
_computing_cell_refinement       'Bruker SAINT [1]'
_computing_data_collection       'Bruker APEX2 [1]'
_computing_data_reduction        'Bruker SAINT [1]'
_computing_molecular_graphics    'ORTEP3 for Windows [4]'
_computing_publication_material  'SHELXL-2014/7 and WINGX [4]'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014) [3]'
_computing_structure_solution    'SIR92 [6]'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1573
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            31984
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.618
_diffrn_reflns_theta_min         4.322
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    6.012
_exptl_absorpt_correction_T_max  0.1960
_exptl_absorpt_correction_T_min  0.1030
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS '
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_description       cubes
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.57
_exptl_crystal_size_min          0.41
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.0076(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1615
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0648P)²+1.0129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1214
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1387
_reflns_number_total             1615
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0130_suppl.cif
_cod_data_source_block           shelx
_cod_database_code               8106748
_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'
'-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 0.05084(4) 0.21611(6) 0.75316(2) 0.0706(3) Uani 1 1 d . . . . .
O2 O -0.00847(19) -0.2979(3) 0.48416(11) 0.0610(6) Uani 1 1 d . . . . .
O3 O 0.18764(18) -0.3619(4) 0.44039(12) 0.0735(7) Uani 1 1 d . . . . .
N1 N 0.1858(2) -0.2062(3) 0.52492(15) 0.0579(7) Uani 1 1 d . . . . .
H1 H 0.256(5) -0.221(5) 0.520(2) 0.087 Uiso 1 1 d . U . . .
C2 C 0.1099(3) -0.2891(4) 0.48368(14) 0.0514(7) Uani 1 1 d . . . . .
C4 C 0.1238(3) -0.4590(5) 0.39248(18) 0.0788(11) Uani 1 1 d . . . . .
H41 H 0.1892 -0.5047 0.3643 0.118 Uiso 1 1 calc R U . . .
H42 H 0.0756 -0.5406 0.4141 0.118 Uiso 1 1 calc R U . . .
H43 H 0.0642 -0.3967 0.3670 0.118 Uiso 1 1 calc R U . . .
C11 C 0.1474(2) -0.1122(4) 0.57745(14) 0.0492(6) Uani 1 1 d . . . . .
C12 C 0.0181(3) -0.0686(4) 0.59023(16) 0.0584(7) Uani 1 1 d . . . . .
H12 H -0.0499 -0.1041 0.5636 0.088 Uiso 1 1 calc R U . . .
C13 C -0.0093(3) 0.0279(4) 0.64274(16) 0.0597(8) Uani 1 1 d . . . . .
H13 H -0.0960 0.0567 0.6514 0.090 Uiso 1 1 calc R U . . .
C14 C 0.0898(3) 0.0812(4) 0.68192(14) 0.0549(7) Uani 1 1 d . . . . .
C15 C 0.2177(3) 0.0391(4) 0.67007(17) 0.0678(9) Uani 1 1 d . . . . .
H15 H 0.2853 0.0752 0.6969 0.102 Uiso 1 1 calc R U . . .
C16 C 0.2451(3) -0.0567(4) 0.61830(16) 0.0666(9) Uani 1 1 d . . . . .
H16 H 0.3322 -0.0854 0.6104 0.100 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
C2 O3 C4 117.0(2) . .
C2 N1 C11 128.8(3) . .
C2 N1 H1 112(4) . .
C11 N1 H1 119(4) . .
O2 C2 O3 124.3(3) . .
O2 C2 N1 126.8(3) . .
O3 C2 N1 108.9(2) . .
O3 C4 H41 109.5 . .
O3 C4 H42 109.5 . .
H41 C4 H42 109.5 . .
O3 C4 H43 109.5 . .
H41 C4 H43 109.5 . .
H42 C4 H43 109.5 . .
C16 C11 C12 118.1(3) . .
C16 C11 N1 117.7(2) . .
C12 C11 N1 124.2(3) . .
C13 C12 C11 119.8(3) . .
C13 C12 H12 120.1 . .
C11 C12 H12 120.1 . .
C14 C13 C12 120.6(3) . .
C14 C13 H13 119.7 . .
C12 C13 H13 119.7 . .
C13 C14 C15 120.4(3) . .
C13 C14 Br1 120.0(2) . .
C15 C14 Br1 119.5(2) . .
C14 C15 C16 119.2(3) . .
C14 C15 H15 120.4 . .
C16 C15 H15 120.4 . .
C15 C16 C11 122.0(3) . .
C15 C16 H16 119.0 . .
C11 C16 H16 119.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C14 1.900(3) .
O2 C2 1.202(4) .
O3 C2 1.338(4) .
O3 C4 1.438(4) .
N1 C2 1.343(4) .
N1 C11 1.397(4) .
N1 H1 0.73(5) .
C4 H41 0.9600 .
C4 H42 0.9600 .
C4 H43 0.9600 .
C11 C16 1.379(4) .
C11 C12 1.387(4) .
C12 C13 1.382(5) .
C12 H12 0.9300 .
C13 C14 1.363(4) .
C13 H13 0.9300 .
C14 C15 1.366(4) .
C15 C16 1.367(5) .
C15 H15 0.9300 .
C16 H16 0.9300 .
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
C4 O3 C2 O2 -1.4(5) . . . .
C4 O3 C2 N1 179.1(3) . . . .
C11 N1 C2 O2 0.2(6) . . . .
C11 N1 C2 O3 179.8(3) . . . .
C2 N1 C11 C16 170.9(3) . . . .
C2 N1 C11 C12 -10.5(5) . . . .
C16 C11 C12 C13 0.0(5) . . . .
N1 C11 C12 C13 -178.5(3) . . . .
C11 C12 C13 C14 0.3(5) . . . .
C12 C13 C14 C15 -0.4(5) . . . .
C12 C13 C14 Br1 179.1(3) . . . .
C13 C14 C15 C16 0.2(5) . . . .
Br1 C14 C15 C16 -179.3(3) . . . .
C14 C15 C16 C11 0.1(6) . . . .
C12 C11 C16 C15 -0.2(5) . . . .
N1 C11 C16 C15 178.4(3) . . . .
