#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/48/2014807.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_2014807
loop_
_publ_author_name
'Martínez-Palau, Meritxell'
'Urpí, Lourdes'
'Font-Bardia, Mercè'
'Puiggalí, Jordi'
_publ_section_title
;
 N,N'-Butane-1,4-diylbis(bromoacetamide)
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o345
_journal_page_last               o347
_journal_paper_doi               10.1107/S0108270105011212
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C8 H14 Br2 N2 O2'
_chemical_formula_moiety         'C8 H14 Br2 N2 O2'
_chemical_formula_sum            'C8 H14 Br2 N2 O2'
_chemical_formula_weight         330.01
_chemical_melting_point          135
_chemical_name_common
;
1,4-bis(bromoacetamide)butane
;
_chemical_name_systematic
;
Butane-1,4-diyl bis(bromoacetamide)
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 109.15(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.7065(18)
_cell_length_b                   7.7518(13)
_cell_length_c                   9.333(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21
_cell_measurement_theta_min      12
_cell_volume                     595.0(3)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Kiers, 1994)'
_computing_data_reduction        'WinGX-PC (version 1.64.05; Farrugia, 1999)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and WinGX-PC'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_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  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0756
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1816
_diffrn_reflns_theta_full        29.97
_diffrn_reflns_theta_max         29.97
_diffrn_reflns_theta_min         2.48
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    6.791
_exptl_absorpt_correction_T_max  0.761
_exptl_absorpt_correction_T_min  0.228
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   '(PLATON; (Spek, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.849
_refine_diff_density_min         -0.539
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     72
_refine_ls_number_reflns         1729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1588
_refine_ls_R_factor_gt           0.0599
_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)+(0.0771P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1593
_reflns_number_gt                837
_reflns_number_total             1729
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg1832.cif
_cod_data_source_block           I
_cod_original_cell_volume        595.1(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2014807
_cod_database_fobs_code          2014807
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_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Br1 0.64331(7) 0.81767(9) 0.12018(8) 0.0742(3) Uani d . 1 . . Br
O3 0.3007(5) 0.6707(5) -0.0964(4) 0.0576(10) Uani d . 1 . . O
N4 0.2009(5) 0.7307(6) 0.0921(5) 0.0440(11) Uani d . 1 . . N
H4 0.223(5) 0.752(6) 0.179(6) 0.027(12) Uiso d . 1 . . H
C2 0.4839(6) 0.6656(7) 0.1575(6) 0.0501(13) Uani d . 1 . . C
H2A 0.5177 0.5467 0.1555 0.060(11) Uiso calc R 1 . . H
H2B 0.4767 0.6889 0.2572 0.060(11) Uiso calc R 1 . . H
C3 0.3202(6) 0.6918(6) 0.0393(5) 0.0403(11) Uani d . 1 . . C
C5 0.0342(6) 0.7510(7) -0.0048(6) 0.0493(13) Uani d . 1 . . C
H5A -0.0372 0.7165 0.0509 0.061(11) Uiso calc R 1 . . H
H5B 0.0142 0.6743 -0.0911 0.061(11) Uiso calc R 1 . . H
C6 -0.0083(6) 0.9349(7) -0.0625(6) 0.0564(14) Uani d . 1 . . C
H6A 0.0621 0.9689 -0.1194 0.093(16) Uiso calc R 1 . . H
H6B -0.1194 0.9370 -0.1314 0.093(16) Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.0539(4) 0.0898(6) 0.0738(5) 0.0013(3) 0.0139(3) 0.0174(4)
O3 0.070(2) 0.076(3) 0.0275(17) 0.0139(19) 0.0177(16) -0.0014(18)
N4 0.050(2) 0.055(3) 0.027(2) 0.008(2) 0.0122(18) 0.000(2)
C2 0.051(3) 0.061(4) 0.040(3) 0.014(2) 0.015(2) 0.005(3)
C3 0.053(3) 0.041(3) 0.028(2) 0.007(2) 0.0139(19) 0.002(2)
C5 0.043(3) 0.052(3) 0.051(3) 0.001(2) 0.012(2) 0.000(3)
C6 0.053(3) 0.060(4) 0.047(3) 0.002(3) 0.005(2) -0.007(3)
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
C3 N4 C5 . 122.8(4)
C3 N4 H4 . 119(3)
C5 N4 H4 . 118(3)
C3 C2 Br1 . 110.4(3)
C3 C2 H2A . 109.6
Br1 C2 H2A . 109.6
C3 C2 H2B . 109.6
Br1 C2 H2B . 109.6
H2A C2 H2B . 108.1
O3 C3 N4 . 123.6(4)
O3 C3 C2 . 120.9(4)
N4 C3 C2 . 115.4(4)
N4 C5 C6 . 113.6(4)
N4 C5 H5A . 108.8
C6 C5 H5A . 108.8
N4 C5 H5B . 108.8
C6 C5 H5B . 108.8
H5A C5 H5B . 107.7
C6 C6 C5 3_575 113.6(6)
C6 C6 H6A 3_575 108.9
C5 C6 H6A . 108.9
C6 C6 H6B 3_575 108.9
C5 C6 H6B . 108.9
H6A C6 H6B . 107.7
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 . 1.938(6) ?
O3 C3 . 1.232(5) ?
N4 C3 . 1.322(6) ?
N4 C5 . 1.445(6) ?
N4 H4 . 0.78(5) ?
C2 C3 . 1.503(7) ?
C2 H2A . 0.97 ?
C2 H2B . 0.97 ?
C5 C6 . 1.526(8) ?
C5 H5A . 0.97 ?
C5 H5B . 0.97 ?
C6 C6 3_575 1.514(11) ?
C6 H6A . 0.97 ?
C6 H6B . 0.97 ?
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
N4 H4 O3 4_576 0.78(5) 2.07(5) 2.853(6) 173(5) yes
C2 H2A O3 3_665 0.97 2.49 3.367(6) 150 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_4
_geom_torsion
_geom_torsion_publ_flag
C5 N4 C3 O3 . 0.5(8) yes
C5 N4 C3 C2 . -176.6(5) yes
Br1 C2 C3 O3 . 58.7(6) yes
Br1 C2 C3 N4 . -124.2(4) yes
C3 N4 C5 C6 . -89.5(6) yes
N4 C5 C6 C6 3_575 -62.1(7) yes
