#------------------------------------------------------------------------------
#$Date: 2017-01-09 05:06:39 +0200 (Mon, 09 Jan 2017) $
#$Revision: 190078 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/70/7227007.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_7227007
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         '2(C5 H6 Br2 N2 O2), 2(C6 H4 N2), C2 H4 Cl2'
_chemical_formula_sum            'C12 H12 Br2 Cl N4 O2'
_chemical_formula_weight         439.53
_chemical_melting_point          421
_chemical_name_systematic
(N,N'-Dibromo-5,5-dimethylhydantoin)(4-cyanopyridine)(1,2-dichloroethane)0.5
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      12
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 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             2016-10-12T09:33:56-00:00
_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                90
_cell_angle_beta                 98.599(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6301(5)
_cell_length_b                   7.7579(7)
_cell_length_c                   23.769(2)
_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                     1573.5(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.996
_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  0.0417
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            4030
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.412
_diffrn_reflns_theta_min         2.6
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.33
_exptl_absorpt_correction_T_max  0.619
_exptl_absorpt_correction_T_min  0.209
_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    1.855
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             860
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 1,2-dichloroethane / hexane'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.603
_refine_diff_density_min         -1.841
_refine_diff_density_rms         0.182
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0536
_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)+(0.0774P)²+7.3800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1428
_reflns_Friedel_coverage         0
_reflns_number_gt                1609
_reflns_number_total             1929
_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_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               7227007
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
_atom_site_refinement_flags_occupancy
C5 C 0.1501(5) 0.8508(6) 0.1231(2) 0.0188(10) Uani 1 1 d . . .
H5 H 0.1981 0.748 0.1361 0.023 Uiso 1 1 calc R U .
C6 C 0.0121(5) 0.8442(6) 0.08538(19) 0.0187(10) Uani 1 1 d . . .
H6 H -0.0329 0.7392 0.0732 0.022 Uiso 1 1 calc R U .
N4 N -0.3153(7) 1 -0.0064(3) 0.0286(14) Uani 1 2 d S T P
C7 C -0.0583(7) 1 0.0659(3) 0.0153(13) Uani 1 2 d S T P
C8 C -0.2020(8) 1 0.0263(3) 0.0203(14) Uani 1 2 d S T P
N3 N 0.2173(6) 1 0.1416(2) 0.0176(12) Uani 1 2 d S T P
C1 C 0.7990(7) 1 0.2363(3) 0.0181(14) Uani 1 2 d S T P
C2 C 0.6674(8) 1 0.3143(3) 0.0162(13) Uani 1 2 d S T P
C3 C 0.8431(8) 1 0.3386(3) 0.0184(14) Uani 1 2 d S T P
C4 C 0.8856(6) 1.1620(7) 0.3734(2) 0.0298(12) Uani 1 1 d . . .
H4A H 0.9969 1.1654 0.3854 0.045 Uiso 1 1 calc R U .
H4B H 0.833 1.1612 0.4063 0.045 Uiso 1 1 calc R U .
H4C H 0.8539 1.2617 0.3507 0.045 Uiso 1 1 calc R U .
C9 C 0.5547(13) 1 0.4869(5) 0.146(10) Uani 1 2 d S T P
H9A H 0.5427 1.1003 0.4623 0.175 Uiso 0.5 1 calc R U P
H9B H 0.5427 0.8997 0.4623 0.175 Uiso 0.5 1 calc R U P
N1 N 0.9075(7) 1 0.2844(3) 0.0295(11) Uani 1 2 d S T P
N2 N 0.6528(7) 1 0.2560(3) 0.0295(11) Uani 1 2 d S T P
O1 O 0.8207(6) 1 0.1879(2) 0.0209(10) Uani 1 2 d S T P
O2 O 0.5613(6) 1 0.3430(2) 0.0229(11) Uani 1 2 d S T P
Br1 Br 1.11730(8) 1 0.27933(3) 0.0264(2) Uani 1 2 d S T P
Br2 Br 0.45782(7) 1 0.20538(3) 0.0162(2) Uani 1 2 d S T P
Cl1 Cl 0.7518(2) 1 0.52182(9) 0.0355(5) Uani 1 2 d S T P
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'
Cl Cl 0.1484 0.1585 '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
N3 C5 C6 122.3(4) . .
N3 C5 H5 118.8 . .
C6 C5 H5 118.8 . .
C5 C6 C7 118.2(4) . .
C5 C6 H6 120.9 . .
C7 C6 H6 120.9 . .
C6 C7 C6 119.4(6) . 6_575
C6 C7 C8 120.3(3) . .
C6 C7 C8 120.3(3) 6_575 .
N4 C8 C7 178.5(7) . .
C5 N3 C5 119.6(6) . 6_575
O1 C1 N1 128.4(6) . .
O1 C1 N2 126.7(6) . .
N1 C1 N2 104.9(6) . .
O2 C2 N2 126.9(6) . .
O2 C2 C3 124.7(6) . .
N2 C2 C3 108.3(5) . .
N1 C3 C4 112.6(4) . 6_575
N1 C3 C4 112.6(4) . .
C4 C3 C4 111.5(6) 6_575 .
N1 C3 C2 98.7(5) . .
C4 C3 C2 110.4(4) 6_575 .
C4 C3 C2 110.4(4) . .
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 . .
C9 C9 Cl1 121.9(13) 5_676 .
C9 C9 H9A 106.9 5_676 .
Cl1 C9 H9A 106.9 . .
C9 C9 H9B 106.9 5_676 .
Cl1 C9 H9B 106.9 . .
H9A C9 H9B 106.7 . .
C1 N1 C3 115.5(5) . .
C1 N1 Br1 120.4(5) . .
C3 N1 Br1 124.2(4) . .
C2 N2 C1 112.5(6) . .
C2 N2 Br2 125.0(5) . .
C1 N2 Br2 122.5(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C5 N3 1.339(5) .
C5 C6 1.381(6) .
C5 H5 0.93 .
C6 C7 1.400(6) .
C6 H6 0.93 .
N4 C8 1.154(9) .
C7 C6 1.400(6) 6_575
C7 C8 1.440(9) .
N3 C5 1.339(5) 6_575
C1 O1 1.192(8) .
C1 N1 1.365(8) .
C1 N2 1.410(8) .
C2 O2 1.221(8) .
C2 N2 1.373(8) .
C2 C3 1.540(9) .
C3 N1 1.476(9) .
C3 C4 1.520(6) 6_575
C3 C4 1.520(6) .
C4 H4A 0.96 .
C4 H4B 0.96 .
C4 H4C 0.96 .
C9 C9 1.21(2) 5_676
C9 Cl1 1.778(11) .
C9 H9A 0.97 .
C9 H9B 0.97 .
N1 Br1 1.833(6) .
N2 Br2 1.916(6) .
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_4
N3 C5 C6 C7 0.4(7) . .
C5 C6 C7 C6 -0.4(9) . 6_575
C5 C6 C7 C8 179.7(5) . .
C6 C5 N3 C5 -0.3(9) . 6_575
O2 C2 C3 N1 180.000(2) . .
N2 C2 C3 N1 0.0000(10) . .
O2 C2 C3 C4 61.9(4) . 6_575
N2 C2 C3 C4 -118.1(4) . 6_575
O2 C2 C3 C4 -61.9(4) . .
N2 C2 C3 C4 118.1(4) . .
O1 C1 N1 C3 180.0000(10) . .
N2 C1 N1 C3 0.0000(10) . .
O1 C1 N1 Br1 0.000(2) . .
N2 C1 N1 Br1 180.0000(10) . .
C4 C3 N1 C1 116.4(4) 6_575 .
C4 C3 N1 C1 -116.5(4) . .
C2 C3 N1 C1 0.0000(10) . .
C4 C3 N1 Br1 -63.6(4) 6_575 .
C4 C3 N1 Br1 63.5(4) . .
C2 C3 N1 Br1 180.0000(10) . .
O2 C2 N2 C1 180.000(2) . .
C3 C2 N2 C1 0.0000(10) . .
O2 C2 N2 Br2 0.000(2) . .
C3 C2 N2 Br2 180.0000(10) . .
O1 C1 N2 C2 180.000(2) . .
N1 C1 N2 C2 0.0000(10) . .
O1 C1 N2 Br2 0.0000(10) . .
N1 C1 N2 Br2 180.0000(10) . .
