#------------------------------------------------------------------------------
#$Date: 2017-01-09 05:06:39 +0200 (Mon, 09 Jan 2017) $
#$Revision: 190078 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/70/7227008.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.
#
data_7227008
loop_
_publ_author_name
'Nicolas, Irène'
'Jeannin, Olivier'
'Pichon, Delphine'
'Fourmigué, Marc'
_publ_section_title
;
 Dibromohydantoins as halogen bond (XB) donors: a route toward the
 introduction of chirality in halogen bonded systems
;
_journal_issue                   48
_journal_name_full               CrystEngComm
_journal_page_first              9325
_journal_paper_doi               10.1039/C6CE02175A
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C5 H6 Br2 N2 O2, 0.5(C4 H4 N2)'
_chemical_formula_sum            'C7 H8 Br2 N3 O2'
_chemical_formula_weight         325.98
_chemical_melting_point          432
_chemical_name_systematic        (N,N'-Dibromo-5,5-dimethylhydantoin)2(pyrazine)
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'iterative - e.g. charge flipping method'
_atom_sites_solution_secondary   'iterative - e.g. charge flipping method'
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2016-10-12T09:44:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2016-10-14 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;
_cell_angle_alpha                64.045(3)
_cell_angle_beta                 81.550(4)
_cell_angle_gamma                85.532(4)
_cell_formula_units_Z            2
_cell_length_a                   7.7140(4)
_cell_length_b                   8.0925(4)
_cell_length_c                   9.1626(4)
_cell_measurement_reflns_used    4089
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.35
_cell_measurement_wavelength     0.71073
_cell_volume                     508.65(4)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis,2007)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_UB_11      0.041224
_diffrn_orient_matrix_UB_12      -0.038938
_diffrn_orient_matrix_UB_13      0.009823
_diffrn_orient_matrix_UB_21      -0.118414
_diffrn_orient_matrix_UB_22      -0.01407
_diffrn_orient_matrix_UB_23      -0.02638
_diffrn_orient_matrix_UB_31      0.077991
_diffrn_orient_matrix_UB_32      -0.00047
_diffrn_orient_matrix_UB_33      -0.028497
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3773
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.034
_diffrn_reflns_theta_max         25.034
_diffrn_reflns_theta_min         2.67
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.946
_exptl_absorpt_correction_T_max  0.356
_exptl_absorpt_correction_T_min  0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.128
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             314
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2 / Hexane'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0282
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0380P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.075
_refine_ls_wR_factor_ref         0.0775
_reflns_Friedel_coverage         0
_reflns_number_gt                1539
_reflns_number_total             1799
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce02175a1.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7227007--7227011.cif.'
_cod_database_code               7227008
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.4977(6) 0.7169(6) 0.7536(5) 0.0160(10) Uani 1 1 d . .
C2 C 0.6865(5) 0.5268(5) 0.6740(5) 0.0120(9) Uani 1 1 d . .
C3 C 0.7816(5) 0.7088(5) 0.6164(5) 0.0126(9) Uani 1 1 d . .
C4 C 0.8313(6) 0.7939(6) 0.4327(5) 0.0176(9) Uani 1 1 d . .
H4A H 0.7288 0.8073 0.3803 0.026 Uiso 1 1 calc R U
H4B H 0.9157 0.716 0.404 0.026 Uiso 1 1 calc R U
H4C H 0.8812 0.9124 0.3975 0.026 Uiso 1 1 calc R U
C5 C 0.9413(6) 0.6762(6) 0.7073(5) 0.0195(10) Uani 1 1 d . .
H5A H 0.9991 0.7906 0.6725 0.029 Uiso 1 1 calc R U
H5B H 1.021 0.5914 0.6836 0.029 Uiso 1 1 calc R U
H5C H 0.9042 0.6261 0.8229 0.029 Uiso 1 1 calc R U
C6 C -0.0489(6) 0.1679(5) 0.9836(5) 0.0142(9) Uani 1 1 d . .
H6 H -0.0871 0.2838 0.9735 0.017 Uiso 1 1 calc R U
C7 C 0.1707(6) -0.0374(6) 0.9862(5) 0.0156(9) Uani 1 1 d . .
H7 H 0.2893 -0.0678 0.9779 0.019 Uiso 1 1 calc R U
N1 N 0.5281(5) 0.5413(4) 0.7564(4) 0.0142(8) Uani 1 1 d . .
N2 N 0.6436(5) 0.8150(5) 0.6662(4) 0.0173(8) Uani 1 1 d . .
N3 N 0.1224(5) 0.1316(5) 0.9686(4) 0.0139(8) Uani 1 1 d . .
O1 O 0.3660(4) 0.7635(4) 0.8157(4) 0.0235(7) Uani 1 1 d . .
O2 O 0.7447(4) 0.3949(4) 0.6513(4) 0.0205(7) Uani 1 1 d . .
Br1 Br 0.35271(5) 0.36087(5) 0.85446(5) 0.01411(14) Uani 1 1 d . .
Br2 Br 0.67369(5) 1.04436(5) 0.65551(5) 0.01532(15) Uani 1 1 d . .
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 0 '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 0.006 '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'
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
O1 C1 N2 129.7(4) . .
O1 C1 N1 124.9(4) . .
N2 C1 N1 105.4(4) . .
O2 C2 N1 127.1(4) . .
O2 C2 C3 125.6(4) . .
N1 C2 C3 107.2(3) . .
N2 C3 C4 111.8(3) . .
N2 C3 C5 112.1(3) . .
C4 C3 C5 111.9(4) . .
N2 C3 C2 100.2(3) . .
C4 C3 C2 110.5(3) . .
C5 C3 C2 109.7(3) . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C3 C5 H5A 109.5 . .
C3 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C3 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
N3 C6 C7 121.4(4) . 2_557
N3 C6 H6 119.3 . .
C7 C6 H6 119.3 2_557 .
N3 C7 C6 121.6(4) . 2_557
N3 C7 H7 119.2 . .
C6 C7 H7 119.2 2_557 .
C2 N1 C1 112.7(3) . .
C2 N1 Br1 126.7(3) . .
C1 N1 Br1 120.5(3) . .
C1 N2 C3 114.1(3) . .
C1 N2 Br2 120.1(3) . .
C3 N2 Br2 124.5(3) . .
C6 N3 C7 117.0(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.206(5) .
C1 N2 1.363(5) .
C1 N1 1.412(5) .
C2 O2 1.215(5) .
C2 N1 1.364(5) .
C2 C3 1.536(5) .
C3 N2 1.462(5) .
C3 C4 1.513(6) .
C3 C5 1.530(5) .
C4 H4A 0.96 .
C4 H4B 0.96 .
C4 H4C 0.96 .
C5 H5A 0.96 .
C5 H5B 0.96 .
C5 H5C 0.96 .
C6 N3 1.331(5) .
C6 C7 1.377(6) 2_557
C6 H6 0.93 .
C7 N3 1.334(5) .
C7 C6 1.377(6) 2_557
C7 H7 0.93 .
N1 Br1 1.890(3) .
N2 Br2 1.846(3) .
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
O2 C2 C3 N2 175.5(4) .
N1 C2 C3 N2 -5.5(4) .
O2 C2 C3 C4 57.4(5) .
N1 C2 C3 C4 -123.5(4) .
O2 C2 C3 C5 -66.5(5) .
N1 C2 C3 C5 112.6(4) .
O2 C2 N1 C1 -177.2(4) .
C3 C2 N1 C1 3.8(4) .
O2 C2 N1 Br1 -1.4(6) .
C3 C2 N1 Br1 179.6(2) .
O1 C1 N1 C2 178.8(4) .
N2 C1 N1 C2 -0.1(4) .
O1 C1 N1 Br1 2.7(6) .
N2 C1 N1 Br1 -176.2(3) .
O1 C1 N2 C3 177.2(4) .
N1 C1 N2 C3 -3.9(4) .
O1 C1 N2 Br2 9.6(6) .
N1 C1 N2 Br2 -171.6(2) .
C4 C3 N2 C1 122.9(4) .
C5 C3 N2 C1 -110.5(4) .
C2 C3 N2 C1 5.8(4) .
C4 C3 N2 Br2 -70.0(4) .
C5 C3 N2 Br2 56.6(4) .
C2 C3 N2 Br2 172.9(3) .
C7 C6 N3 C7 -0.8(6) 2_557
C6 C7 N3 C6 0.8(6) 2_557
