#------------------------------------------------------------------------------
#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/27/1572727.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_1572727
loop_
_publ_author_name
'Schwarzer, Anke'
'Stapf, Manuel'
_publ_section_title
;
 2-Bromoacetamide
;
_journal_coeditor_code           BH4089
_journal_issue                   9
_journal_name_full               IUCrData
_journal_page_first              x240863
_journal_paper_doi               10.1107/S2414314624008630
_journal_volume                  9
_journal_year                    2024
_chemical_formula_iupac          'C2 H4 Br N O'
_chemical_formula_moiety         'C2 H4 Br N O'
_chemical_formula_sum            'C2 H4 Br N O'
_chemical_formula_weight         137.97
_chemical_name_systematic
;
2-Bromoacetamide
;
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 99.94(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.373(4)
_cell_length_b                   5.1899(14)
_cell_length_c                   7.557(3)
_cell_measurement_reflns_used    1778
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      22.49
_cell_measurement_theta_min      1.74
_cell_volume                     400.7(2)
_computing_cell_refinement
;
X-Area (Stoe & Cie, 2023)
;
_computing_data_collection
;
X-Area (Stoe & Cie, 2023)
;
_computing_data_reduction
;
X-Area (Stoe & Cie, 2023)
;
_computing_molecular_graphics
;
XP (Sheldrick, 2008)
;
_computing_publication_material
;
WinGX (Farrugia, 2012), publCIF (Westrip, 2010)
and
ShelXle (Hübschle et al.,  2011)
;
_computing_structure_refinement
;
SHELXL2019/2 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018/2 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      93(2)
_diffrn_detector                 'Pilatus 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 1.000
_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           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4506
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.976
_diffrn_reflns_theta_min         1.993
_diffrn_source                   'Primux 50 Mo'
_diffrn_source_current           0.830
_diffrn_source_power             0.050
_diffrn_source_voltage           60
_exptl_absorpt_coefficient_mu    10.060
_exptl_absorpt_correction_T_max  0.6679
_exptl_absorpt_correction_T_min  0.3296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[X-Red32 (Stoe & Cie, 2023; Koziskova et al., 2016]
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.287
_exptl_crystal_description       plate
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.506
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     52
_refine_ls_number_reflns         879
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0275
_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)+(0.0417P)²+0.0569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0654
_refine_ls_wR_factor_ref         0.0682
_reflns_number_gt                731
_reflns_number_total             879
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bh4089.cif
_cod_data_source_block           I
_cod_original_cell_volume        400.7(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1572727
#BEGIN Tags that were not found in dictionaries:
_shelx_estimated_absorpt_t_min   0.404
_shelx_estimated_absorpt_t_max   0.689
#END Tags that were not found in dictionaries
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 0.61180(3) 0.82582(6) 0.68653(4) 0.01566(15) Uani d 1 . .
O O1 0.8681(3) 0.2945(4) 0.5541(3) 0.0181(6) Uani d 1 . .
N N1 0.8855(3) 0.7271(6) 0.5813(4) 0.0174(7) Uani d 1 . .
H H1N 0.854(4) 0.863(7) 0.608(6) 0.026 Uiso d 1 . .
H H2N 0.950(5) 0.735(8) 0.550(6) 0.026 Uiso d 1 . .
C C1 0.8257(3) 0.5060(7) 0.5962(4) 0.0140(7) Uani d 1 . .
C C2 0.6997(3) 0.4974(6) 0.6709(5) 0.0160(7) Uani d 1 . .
H H2A 0.718682 0.421332 0.792727 0.019 Uiso calc 1 . .
H H2B 0.638276 0.380045 0.594915 0.019 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
30 17 10 0.0667
30 -4 3 0.0783
30 -14 -1 0.0910
30 4 -9 0.0943
14 8 -15 0.0979
-3 -2 15 0.1196
-30 1 4 0.0693
-30 2 -7 0.1064
-30 10 3 0.0666
-15 -1 8 0.1044
-1 -15 0 0.0554
7 6 -30 0.0877
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
C1 N1 H1N . . 121(3) ?
C1 N1 H2N . . 122(3) ?
H1N N1 H2N . . 117(5) ?
O1 C1 N1 . . 123.7(3) ?
O1 C1 C2 . . 115.8(3) ?
N1 C1 C2 . . 120.5(3) ?
C1 C2 Br1 . . 116.2(2) ?
C1 C2 H2A . . 108.2 ?
Br1 C2 H2A . . 108.2 ?
C1 C2 H2B . . 108.2 ?
Br1 C2 H2B . . 108.2 ?
H2A C2 H2B . . 107.4 ?
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 C2 . 1.946(3) ?
O1 C1 . 1.244(4) ?
N1 C1 . 1.318(5) ?
N1 H1N . 0.82(4) ?
N1 H2N . 0.75(5) ?
C1 C2 . 1.512(5) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
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
_geom_hbond_publ_flag
N1 H1N Br1 . 0.82(4) 2.69(4) 3.120(3) 115(3) yes
N1 H1N O1 1_565 0.82(4) 2.29(4) 2.955(4) 140(4) yes
N1 H2N O1 3_766 0.75(5) 2.17(5) 2.915(5) 172(5) yes
C2 H2B Br1 1_545 0.99 2.98 3.610(3) 122 yes
C2 H2A O1 4_566 0.99 2.55 3.462(4) 153 yes
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
O1 C1 C2 Br1 . . . . -166.7(2) no
N1 C1 C2 Br1 . . . . 14.4(4) no
