#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/72/2237266.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_2237266
loop_
_publ_author_name
'Köppen, Robert'
'Emmerling, Franziska'
'Koch, Matthias'
_publ_section_title
;
 rac-2,3-Dibromopropionamide
;
_journal_coeditor_code           BG2488
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o151
_journal_paper_doi               10.1107/S160053681205132X
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C3 H5 Br2 N O'
_chemical_formula_moiety         'C3 H5 Br2 N O'
_chemical_formula_sum            'C3 H5 Br2 N O'
_chemical_formula_weight         230.88
_chemical_name_common            rac-2,3-Dibromopropionamide
_chemical_name_systematic
;
rac-2,3-Dibromopropionamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.574(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.926(3)
_cell_length_b                   6.5911(14)
_cell_length_c                   8.991(2)
_cell_measurement_reflns_used    756
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.59
_cell_measurement_theta_min      2.47
_cell_volume                     687.0(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1813
_diffrn_reflns_av_sigmaI/netI    0.1850
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4500
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    11.697
_exptl_absorpt_correction_T_max  0.56
_exptl_absorpt_correction_T_min  0.23
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          .14
_exptl_crystal_size_mid          .11
_exptl_crystal_size_min          .05
_refine_diff_density_max         0.863
_refine_diff_density_min         -0.500
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.773
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         1556
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.773
_refine_ls_R_factor_all          0.1967
_refine_ls_R_factor_gt           0.0657
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0796P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1841
_reflns_number_gt                470
_reflns_number_total             1556
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bg2488.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2237266
_cod_database_fobs_code          2237266
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Br Br1 0.40891(12) 0.3123(3) 0.39780(17) 0.1139(8) Uani d . 1 1
Br Br2 0.19816(12) -0.1953(2) 0.11104(17) 0.1065(7) Uani d . 1 1
O O1 0.1347(5) 0.0988(12) 0.3970(9) 0.067(2) Uani d . 1 1
N N1 0.0718(7) 0.2806(13) 0.1819(10) 0.072(3) Uani d . 1 1
H H1 0.0110 0.3215 0.2088 0.087 Uiso d R 1 1
H H2 0.0844 0.3184 0.0957 0.087 Uiso d R 1 1
C C1 0.3463(10) 0.030(2) 0.3142(14) 0.107(5) Uani d . 1 1
H H4 0.3995 -0.0396 0.2652 0.129 Uiso calc R 1 1
H H5 0.3291 -0.0550 0.3939 0.129 Uiso calc R 1 1
C C2 0.2455(8) 0.0907(19) 0.2077(12) 0.077(3) Uani d . 1 1
H H3 0.2622 0.1865 0.1325 0.092 Uiso calc R 1 1
C C3 0.1452(8) 0.1613(15) 0.2720(13) 0.054(3) Uani d . 1 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
C3 N1 H1 120.1
C3 N1 H2 119.9
H1 N1 H2 120.0
C2 C1 Br1 99.8(9)
C2 C1 H4 111.8
Br1 C1 H4 111.8
C2 C1 H5 111.8
Br1 C1 H5 111.8
H4 C1 H5 109.5
C1 C2 C3 116.9(10)
C1 C2 Br2 97.5(9)
C3 C2 Br2 105.9(7)
C1 C2 H3 111.8
C3 C2 H3 111.8
Br2 C2 H3 111.8
O1 C3 N1 124.8(9)
O1 C3 C2 120.2(10)
N1 C3 C2 114.9(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 2.077(15)
Br2 C2 2.097(12)
O1 C3 1.231(10)
N1 C3 1.307(12)
N1 H1 0.8597
N1 H2 0.8604
C1 C2 1.407(14)
C1 H4 0.9700
C1 H5 0.9700
C2 C3 1.518(13)
C2 H3 0.9800
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
N1 H1 O1 2_555 0.86 2.55 3.185(11) 132
N1 H2 O1 4_565 0.86 2.09 2.942(12) 173
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
Br1 C1 C2 C3 -74.1(11)
Br1 C1 C2 Br2 173.7(4)
C1 C2 C3 O1 -26.7(17)
Br2 C2 C3 O1 80.6(10)
C1 C2 C3 N1 156.6(12)
Br2 C2 C3 N1 -96.1(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 77387
