# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1509929'
_audit_update_record             
;
2016-10-14 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;

_audit_creation_date             2016-10-12T09:33:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C12 H12 Br2 Cl N4 O2'
_chemical_formula_moiety         '2(C5 H6 Br2 N2 O2), 2(C6 H4 N2), C2 H4 Cl2'
_chemical_formula_weight         439.53

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/m'
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_Int_Tables_number      12
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'

_cell_length_a                   8.6301(5)
_cell_length_b                   7.7579(7)
_cell_length_c                   23.769(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.599(4)
_cell_angle_gamma                90
_cell_volume                     1573.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4089
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      27.47
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.855
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             860

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    5.33
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.209
_exptl_absorpt_correction_T_max  0.619

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.2914  0.7456                #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_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_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_number            4030
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.6
_diffrn_reflns_theta_max         27.412
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_coverage         0
_reflns_number_total             1929
_reflns_number_gt                1609
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis,2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'iterative - e.g. charge flipping method'
_atom_sites_solution_secondary   'iterative - e.g. charge flipping method'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0774P)²+7.3800P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1929
_refine_ls_number_parameters     115
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1428
_refine_ls_wR_factor_gt          0.1346
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.603
_refine_diff_density_min         -1.841
_refine_diff_density_rms         0.182

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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) . . . . ?


# END of CIF
_chemical_name_systematic        
(N,N'-Dibromo-5,5-dimethylhydantoin)(4-cyanopyridine)(1,2-dichloroethane)0.5
_chemical_melting_point          421
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1,2-dichloroethane / hexane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1509930'
_audit_update_record             
;
2016-10-14 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;

_audit_creation_date             2016-10-12T09:44:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C7 H8 Br2 N3 O2'
_chemical_formula_moiety         'C5 H6 Br2 N2 O2, 0.5(C4 H4 N2)'
_chemical_formula_weight         325.98

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7140(4)
_cell_length_b                   8.0925(4)
_cell_length_c                   9.1626(4)
_cell_angle_alpha                64.045(3)
_cell_angle_beta                 81.550(4)
_cell_angle_gamma                85.532(4)
_cell_volume                     508.65(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4089
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      27.47
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_exptl_crystal_density_diffrn    2.128
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             314

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    7.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.106
_exptl_absorpt_correction_T_max  0.356

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.3987  1.0000                #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_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_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_number            3773
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         25.034
_diffrn_reflns_theta_full        25.034
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             1799
_reflns_number_gt                1539
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis,2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'iterative - e.g. charge flipping method'
_atom_sites_solution_secondary   'iterative - e.g. charge flipping method'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0380P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1799
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0282
_refine_ls_wR_factor_ref         0.0775
_refine_ls_wR_factor_gt          0.075
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.135

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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 . . . ?


# END of CIF
_chemical_name_systematic        
(N,N'-Dibromo-5,5-dimethylhydantoin)2(pyrazine)
_chemical_melting_point          432
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2 / Hexane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1509931'
_audit_update_record             
;
2016-10-14 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;

_audit_creation_date             2016-10-12T09:39:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C12 H13 Br2 N3 O4'
_chemical_formula_moiety         'C12 H13 Br2 N3 O4'
_chemical_formula_weight         423.07

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1692(8)
_cell_length_b                   7.9700(10)
_cell_length_c                   15.743(2)
_cell_angle_alpha                88.236(5)
_cell_angle_beta                 81.458(5)
_cell_angle_gamma                85.411(5)
_cell_volume                     762.90(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4089
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      27.47
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    5.331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.116
_exptl_absorpt_correction_T_max  0.726

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.3741  0.7456                #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------#



#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_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_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_number            5692
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.617
_diffrn_reflns_theta_max         27.578
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.976
_reflns_Friedel_coverage         0
_reflns_number_total             3446
_reflns_number_gt                2684
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis,2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'iterative - e.g. charge flipping method'
_atom_sites_solution_secondary   'iterative - e.g. charge flipping method'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1190P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3446
_refine_ls_number_parameters     199
_refine_ls_number_restraints     6
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.072
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1774
_refine_ls_wR_factor_gt          0.1645
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.422
_refine_diff_density_min         -1.173
_refine_diff_density_rms         0.209

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0402(10) 0.2343(8) 0.1620(5) 0.0314(14) Uani 1 1 d . . . . .
H1 H 0.0033 0.1236 0.1612 0.038 Uiso 1 1 calc R U . . .
C2 C -0.0879(10) 0.3611(10) 0.1270(5) 0.0415(17) Uani 1 1 d . . . . .
H2 H -0.2106 0.3351 0.1036 0.05 Uiso 1 1 calc R U . . .
C3 C -0.0342(10) 0.5260(9) 0.1267(4) 0.0356(15) Uani 1 1 d . . . . .
C4 C 0.1492(10) 0.5598(8) 0.1643(5) 0.0360(15) Uani 1 1 d . . . . .
H4 H 0.1889 0.6694 0.1671 0.043 Uiso 1 1 calc R U . . .
C5 C 0.2674(10) 0.4281(7) 0.1965(4) 0.0301(14) Uani 1 1 d . . . . .
H5 H 0.3917 0.4511 0.2197 0.036 Uiso 1 1 calc R U . . .
C8 C 0.6411(8) -0.2521(6) 0.3000(4) 0.0206(11) Uani 1 1 d . . . . .
C9 C 0.7649(8) -0.0464(6) 0.3756(4) 0.0204(11) Uani 1 1 d . . . . .
C10 C 0.8492(8) -0.2175(6) 0.4124(4) 0.0198(11) Uani 1 1 d . . . . .
C11 C 1.0978(9) -0.2355(7) 0.4012(4) 0.0237(12) Uani 1 1 d . . . . .
H11A H 1.1463 -0.347 0.4186 0.036 Uiso 1 1 calc R U . . .
H11B H 1.1493 -0.1546 0.4359 0.036 Uiso 1 1 calc R U . . .
H11C H 1.1554 -0.2163 0.3419 0.036 Uiso 1 1 calc R U . . .
C12 C 0.7429(10) -0.2356(7) 0.5051(4) 0.0273(13) Uani 1 1 d . . . . .
H12A H 0.5871 -0.2097 0.509 0.041 Uiso 1 1 calc R U . . .
H12B H 0.8028 -0.1594 0.5399 0.041 Uiso 1 1 calc R U . . .
H12C H 0.7715 -0.349 0.5251 0.041 Uiso 1 1 calc R U . . .
N1 N 0.2180(8) 0.2689(6) 0.1972(4) 0.0286(11) Uani 1 1 d . . . . .
N2 N 0.6463(7) -0.0787(5) 0.3132(3) 0.0211(10) Uani 1 1 d . . . . .
N3 N 0.7670(8) -0.3308(5) 0.3551(3) 0.0258(11) Uani 1 1 d . . . . .
O3 O 0.5455(6) -0.3142(5) 0.2478(3) 0.0254(9) Uani 1 1 d . . . . .
O4 O 0.8002(6) 0.0893(4) 0.4011(3) 0.0265(9) Uani 1 1 d . . . . .
Br1 Br 0.45413(8) 0.07858(6) 0.25800(4) 0.0233(2) Uani 1 1 d . . . . .
Br2 Br 0.77510(8) -0.56219(6) 0.36997(4) 0.0231(2) Uani 1 1 d . . . . .
O1A O -0.1040(14) 0.8127(10) 0.0873(6) 0.0563(16) Uani 0.756(15) 1 d D . P A 1
O2A O -0.3343(18) 0.6175(13) 0.0565(9) 0.0563(16) Uani 0.756(15) 1 d D . P A 1
C6A C -0.1609(12) 0.6730(10) 0.0904(5) 0.065(3) Uani 0.756(15) 1 d D . P A 1
C7A C -0.4635(17) 0.7771(13) 0.0321(7) 0.053(3) Uani 0.756(15) 1 d D . P A 1
H7A1 H -0.5107 0.8435 0.0822 0.08 Uiso 0.756(15) 1 calc R U P A 1
H7A2 H -0.5896 0.7483 0.0081 0.08 Uiso 0.756(15) 1 calc R U P A 1
H7A3 H -0.3719 0.8407 -0.0097 0.08 Uiso 0.756(15) 1 calc R U P A 1
O2B O -0.136(5) 0.8338(17) 0.1111(17) 0.0563(16) Uani 0.244(15) 1 d D . P A 2
O1B O -0.313(6) 0.652(4) 0.054(3) 0.0563(16) Uani 0.244(15) 1 d D . P A 2
C6B C -0.1609(12) 0.6730(10) 0.0904(5) 0.065(3) Uani 0.244(15) 1 d D . P A 2
C7B C -0.269(5) 0.904(4) 0.0427(19) 0.045(9) Uiso 0.244(15) 1 d D . P A 2
H7B1 H -0.1707 0.9339 -0.0078 0.067 Uiso 0.244(15) 1 calc R U P A 2
H7B2 H -0.3586 1.0021 0.0638 0.067 Uiso 0.244(15) 1 calc R U P A 2
H7B3 H -0.3607 0.8204 0.0286 0.067 Uiso 0.244(15) 1 calc R U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.352(8) . ?
C1 C2 1.384(9) . ?
C1 H1 0.93 . ?
C2 C3 1.381(10) . ?
C2 H2 0.93 . ?
C3 C4 1.399(10) . ?
C3 C6B 1.502(10) . ?
C3 C6A 1.502(10) . ?
C4 C5 1.358(8) . ?
C4 H4 0.93 . ?
C5 N1 1.328(7) . ?
C5 H5 0.93 . ?
C8 O3 1.218(7) . ?
C8 N3 1.357(7) . ?
C8 N2 1.408(6) . ?
C9 O4 1.212(6) . ?
C9 N2 1.351(7) . ?
C9 C10 1.547(7) . ?
C10 N3 1.465(7) . ?
C10 C11 1.513(7) . ?
C10 C12 1.516(8) . ?
C11 H11A 0.96 . ?
C11 H11B 0.96 . ?
C11 H11C 0.96 . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
N1 Br1 2.304(5) . ?
N2 Br1 1.932(4) . ?
N3 Br2 1.849(4) . ?
O1A C6A 1.192(8) . ?
O2A C6A 1.373(8) . ?
O2A C7A 1.516(8) . ?
C7A H7A1 0.96 . ?
C7A H7A2 0.96 . ?
C7A H7A3 0.96 . ?
O2B C6B 1.358(10) . ?
O2B C7B 1.514(10) . ?
O1B C6B 1.197(10) . ?
C7B H7B1 0.96 . ?
C7B H7B2 0.96 . ?
C7B H7B3 0.96 . ?

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
_geom_angle_publ_flag
N1 C1 C2 121.1(6) . . ?
N1 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C3 C2 C1 120.3(6) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 117.9(6) . . ?
C2 C3 C6B 124.7(6) . . ?
C4 C3 C6B 117.3(6) . . ?
C2 C3 C6A 124.7(6) . . ?
C4 C3 C6A 117.3(6) . . ?
C5 C4 C3 118.2(6) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
N1 C5 C4 124.6(6) . . ?
N1 C5 H5 117.7 . . ?
C4 C5 H5 117.7 . . ?
O3 C8 N3 128.6(5) . . ?
O3 C8 N2 125.8(5) . . ?
N3 C8 N2 105.6(5) . . ?
O4 C9 N2 128.2(5) . . ?
O4 C9 C10 124.2(5) . . ?
N2 C9 C10 107.6(4) . . ?
N3 C10 C11 110.5(4) . . ?
N3 C10 C12 112.7(5) . . ?
C11 C10 C12 113.4(5) . . ?
N3 C10 C9 99.4(4) . . ?
C11 C10 C9 111.1(4) . . ?
C12 C10 C9 108.9(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 N1 C1 117.9(5) . . ?
C5 N1 Br1 115.2(4) . . ?
C1 N1 Br1 126.9(4) . . ?
C9 N2 C8 112.8(4) . . ?
C9 N2 Br1 127.4(4) . . ?
C8 N2 Br1 118.9(4) . . ?
C8 N3 C10 114.3(4) . . ?
C8 N3 Br2 120.2(4) . . ?
C10 N3 Br2 124.2(4) . . ?
N2 Br1 N1 177.8(2) . . ?
C6A O2A C7A 104.6(8) . . ?
O1A C6A O2A 127.1(9) . . ?
O1A C6A C3 123.0(8) . . ?
O2A C6A C3 109.6(7) . . ?
O2A C7A H7A1 109.5 . . ?
O2A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
O2A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
C6B O2B C7B 91.8(16) . . ?
O1B C6B O2B 116(2) . . ?
O1B C6B C3 120.9(17) . . ?
O2B C6B C3 121.6(12) . . ?
O2B C7B H7B1 109.5 . . ?
O2B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
O2B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
H7B2 C7B H7B3 109.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.8(11) . . . . ?
C1 C2 C3 C4 -1.4(10) . . . . ?
C1 C2 C3 C6B 179.8(7) . . . . ?
C1 C2 C3 C6A 179.8(7) . . . . ?
C2 C3 C4 C5 1.9(10) . . . . ?
C6B C3 C4 C5 -179.2(6) . . . . ?
C6A C3 C4 C5 -179.2(6) . . . . ?
C3 C4 C5 N1 -2.0(11) . . . . ?
O4 C9 C10 N3 -177.4(5) . . . . ?
N2 C9 C10 N3 3.7(5) . . . . ?
O4 C9 C10 C11 -61.0(7) . . . . ?
N2 C9 C10 C11 120.1(5) . . . . ?
O4 C9 C10 C12 64.5(7) . . . . ?
N2 C9 C10 C12 -114.4(5) . . . . ?
C4 C5 N1 C1 1.4(10) . . . . ?
C4 C5 N1 Br1 -179.6(6) . . . . ?
C2 C1 N1 C5 -0.7(10) . . . . ?
C2 C1 N1 Br1 -179.6(5) . . . . ?
O4 C9 N2 C8 179.6(5) . . . . ?
C10 C9 N2 C8 -1.5(6) . . . . ?
O4 C9 N2 Br1 -11.4(9) . . . . ?
C10 C9 N2 Br1 167.5(3) . . . . ?
O3 C8 N2 C9 179.9(5) . . . . ?
N3 C8 N2 C9 -1.6(6) . . . . ?
O3 C8 N2 Br1 9.8(8) . . . . ?
N3 C8 N2 Br1 -171.6(4) . . . . ?
O3 C8 N3 C10 -177.1(5) . . . . ?
N2 C8 N3 C10 4.4(6) . . . . ?
O3 C8 N3 Br2 -9.9(9) . . . . ?
N2 C8 N3 Br2 171.6(4) . . . . ?
C11 C10 N3 C8 -121.8(5) . . . . ?
C12 C10 N3 C8 110.2(5) . . . . ?
C9 C10 N3 C8 -5.0(6) . . . . ?
C11 C10 N3 Br2 71.6(6) . . . . ?
C12 C10 N3 Br2 -56.4(6) . . . . ?
C9 C10 N3 Br2 -171.6(4) . . . . ?
C7A O2A C6A O1A -11.7(15) . . . . ?
C7A O2A C6A C3 173.4(8) . . . . ?
C2 C3 C6A O1A -176.2(8) . . . . ?
C4 C3 C6A O1A 5.0(12) . . . . ?
C2 C3 C6A O2A -1.1(11) . . . . ?
C4 C3 C6A O2A -179.9(9) . . . . ?
C7B O2B C6B O1B -22(3) . . . . ?
C7B O2B C6B C3 170.2(14) . . . . ?
C2 C3 C6B O1B -5(3) . . . . ?
C4 C3 C6B O1B 176(3) . . . . ?
C2 C3 C6B O2B 162.7(16) . . . . ?
C4 C3 C6B O2B -16.1(18) . . . . ?


# END of CIF
_chemical_name_systematic        
(N,N'-Dibromo-5,5-dimethylhydantoin)(methylisonicotinate)
_chemical_melting_point          407
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chlorobenzene / Hexane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1509932'
_audit_update_record             
;
2016-10-14 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;

_audit_creation_date             2016-10-12T09:49:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C14 H17 Br2 N3 O4'
_chemical_formula_moiety         'C7 H10 Br2 N2 O2, C7 H7 N O2'
_chemical_formula_weight         451.12
_chemical_absolute_configuration syn

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.5779(5)
_cell_length_b                   7.9462(5)
_cell_length_c                   32.486(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1698.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5749
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      27.39
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.587
_exptl_absorpt_correction_T_max  0.746

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_orient_matrix_ub_11      0.090828
_diffrn_orient_matrix_ub_12      0.043616
_diffrn_orient_matrix_ub_13      -0.02226
_diffrn_orient_matrix_ub_21      0.101109
_diffrn_orient_matrix_ub_22      0.03645
_diffrn_orient_matrix_ub_23      0.021188
_diffrn_orient_matrix_ub_31      0.068108
_diffrn_orient_matrix_ub_32      -0.112277
_diffrn_orient_matrix_ub_33      -0.001769
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_number            13213
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         2.508
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_coverage         0.701
_reflns_number_total             3881
_reflns_number_gt                3351
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.27B integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0126P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3881
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0574
_refine_ls_wR_factor_gt          0.0545
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1242 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(8)
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.42
_refine_diff_density_rms         0.089

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br 0.02318(8) 0.37227(5) 0.83862(2) 0.02229(12) Uani 1 1 d . . . . .
Br02 Br 0.02187(7) -0.23518(5) 0.93022(2) 0.01870(11) Uani 1 1 d . . . . .
O4 O 0.0329(5) -0.8933(3) 1.08184(9) 0.0233(7) Uani 1 1 d . . . . .
O2 O -0.0861(4) -0.2756(4) 0.83130(9) 0.0217(7) Uani 1 1 d . . . . .
O3 O 0.0771(5) -0.6767(4) 1.12594(10) 0.0278(8) Uani 1 1 d . . . . .
N2 N 0.0570(6) 0.1433(4) 0.84618(11) 0.0188(9) Uani 1 1 d . . . . .
N3 N 0.0428(6) -0.4058(4) 0.98744(11) 0.0215(9) Uani 1 1 d . . . . .
O1 O 0.0856(5) 0.1572(4) 0.91730(10) 0.0283(9) Uani 1 1 d . . . . .
N1 N 0.0013(7) -0.0889(4) 0.88294(10) 0.0182(8) Uani 1 1 d . . . . .
C10 C 0.0521(6) -0.6211(5) 1.05425(13) 0.0176(9) Uani 1 1 d . . . . .
C3 C -0.0310(7) 0.0226(5) 0.81718(12) 0.0162(9) Uani 1 1 d . . . . .
H012 H -0.1719 0.0592 0.81 0.019 Uiso 1 1 calc R U . . .
C11 C 0.0364(7) -0.4494(5) 1.05990(13) 0.0211(10) Uani 1 1 d . . . . .
H013 H 0.0297 -0.4032 1.0868 0.025 Uiso 1 1 calc R U . . .
C12 C 0.0308(7) -0.3456(5) 1.02561(13) 0.0206(10) Uani 1 1 d . . . . .
H014 H 0.0178 -0.2275 1.0295 0.025 Uiso 1 1 calc R U . . .
C2 C -0.0425(6) -0.1364(5) 0.84368(13) 0.0177(9) Uani 1 1 d . . . . .
C7 C 0.3869(8) -0.1546(6) 0.81175(15) 0.0280(12) Uani 1 1 d . . . . .
H01A H 0.3469 -0.124 0.8398 0.042 Uiso 1 1 calc R U . . .
H01B H 0.5347 -0.1692 0.8105 0.042 Uiso 1 1 calc R U . . .
H01C H 0.32 -0.2601 0.8039 0.042 Uiso 1 1 calc R U . . .
C5 C 0.3229(7) -0.0150(6) 0.78204(14) 0.0208(10) Uani 1 1 d . . . . .
H017 H 0.3761 0.0945 0.7927 0.025 Uiso 1 1 calc R U . . .
C13 C 0.0562(7) -0.7310(5) 1.09168(14) 0.0198(10) Uani 1 1 d . . . . .
C1 C 0.0503(7) 0.0833(5) 0.88598(14) 0.0204(10) Uani 1 1 d . . . . .
C4 C 0.0921(7) -0.0004(5) 0.77743(14) 0.0197(10) Uani 1 1 d . . . . .
H02A H 0.0423 -0.103 0.7634 0.024 Uiso 1 1 calc R U . . .
H02B H 0.0628 0.0962 0.7591 0.024 Uiso 1 1 calc R U . . .
C9 C 0.0653(7) -0.6829(5) 1.01453(14) 0.0256(12) Uani 1 1 d . . . . .
H021 H 0.0765 -0.8005 1.0099 0.031 Uiso 1 1 calc R U . . .
C6 C 0.4178(8) -0.0476(7) 0.73978(15) 0.0344(14) Uani 1 1 d . . . . .
H02C H 0.3784 -0.1597 0.7301 0.052 Uiso 1 1 calc R U . . .
H02D H 0.5662 -0.0412 0.742 0.052 Uiso 1 1 calc R U . . .
H02E H 0.3696 0.0374 0.7202 0.052 Uiso 1 1 calc R U . . .
C8 C 0.0621(8) -0.5726(5) 0.98181(15) 0.0296(13) Uani 1 1 d . . . . .
H023 H 0.0737 -0.6155 0.9546 0.036 Uiso 1 1 calc R U . . .
C14 C 0.0277(8) -1.0101(5) 1.11578(13) 0.0250(11) Uani 1 1 d . . . . .
H14A H 0.1628 -1.0598 1.1196 0.037 Uiso 1 1 calc R U . . .
H14B H -0.071 -1.0994 1.1099 0.037 Uiso 1 1 calc R U . . .
H14C H -0.0123 -0.9506 1.1409 0.037 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br01 N2 1.849(3) . ?
Br02 N1 1.931(3) . ?
Br02 N3 2.305(4) . ?
O4 C13 1.337(5) . ?
O4 C14 1.442(5) . ?
O2 C2 1.211(5) . ?
O3 C13 1.202(5) . ?
N2 C1 1.379(6) . ?
N2 C3 1.464(5) . ?
N3 C12 1.332(5) . ?
N3 C8 1.344(5) . ?
O1 C1 1.197(5) . ?
N1 C2 1.361(5) . ?
N1 C1 1.410(5) . ?
C10 C11 1.380(6) . ?
C10 C9 1.383(6) . ?
C10 C13 1.498(6) . ?
C3 C2 1.531(5) . ?
C3 C4 1.535(6) . ?
C3 H012 1 . ?
C11 C12 1.387(6) . ?
C11 H013 0.95 . ?
C12 H014 0.95 . ?
C7 C5 1.530(6) . ?
C7 H01A 0.98 . ?
C7 H01B 0.98 . ?
C7 H01C 0.98 . ?
C5 C4 1.530(6) . ?
C5 C6 1.530(7) . ?
C5 H017 1 . ?
C4 H02A 0.99 . ?
C4 H02B 0.99 . ?
C9 C8 1.378(6) . ?
C9 H021 0.95 . ?
C6 H02C 0.98 . ?
C6 H02D 0.98 . ?
C6 H02E 0.98 . ?
C8 H023 0.95 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?

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
_geom_angle_publ_flag
N1 Br02 N3 178.83(14) . . ?
C13 O4 C14 116.2(3) . . ?
C1 N2 C3 111.3(3) . . ?
C1 N2 Br01 117.4(3) . . ?
C3 N2 Br01 120.8(3) . . ?
C12 N3 C8 119.1(4) . . ?
C12 N3 Br02 122.4(3) . . ?
C8 N3 Br02 118.4(3) . . ?
C2 N1 C1 112.6(3) . . ?
C2 N1 Br02 126.4(3) . . ?
C1 N1 Br02 120.8(3) . . ?
C11 C10 C9 118.7(4) . . ?
C11 C10 C13 118.0(4) . . ?
C9 C10 C13 123.3(4) . . ?
N2 C3 C2 101.5(3) . . ?
N2 C3 C4 114.2(4) . . ?
C2 C3 C4 113.7(4) . . ?
N2 C3 H012 109 . . ?
C2 C3 H012 109 . . ?
C4 C3 H012 109 . . ?
C10 C11 C12 118.9(4) . . ?
C10 C11 H013 120.5 . . ?
C12 C11 H013 120.5 . . ?
N3 C12 C11 122.2(4) . . ?
N3 C12 H014 118.9 . . ?
C11 C12 H014 118.9 . . ?
O2 C2 N1 127.9(4) . . ?
O2 C2 C3 125.4(4) . . ?
N1 C2 C3 106.7(3) . . ?
C5 C7 H01A 109.5 . . ?
C5 C7 H01B 109.5 . . ?
H01A C7 H01B 109.5 . . ?
C5 C7 H01C 109.5 . . ?
H01A C7 H01C 109.5 . . ?
H01B C7 H01C 109.5 . . ?
C7 C5 C4 112.9(4) . . ?
C7 C5 C6 109.3(4) . . ?
C4 C5 C6 109.3(4) . . ?
C7 C5 H017 108.4 . . ?
C4 C5 H017 108.4 . . ?
C6 C5 H017 108.4 . . ?
O3 C13 O4 125.5(4) . . ?
O3 C13 C10 123.0(4) . . ?
O4 C13 C10 111.5(4) . . ?
O1 C1 N2 128.4(4) . . ?
O1 C1 N1 125.5(4) . . ?
N2 C1 N1 106.1(4) . . ?
C5 C4 C3 116.7(4) . . ?
C5 C4 H02A 108.1 . . ?
C3 C4 H02A 108.1 . . ?
C5 C4 H02B 108.1 . . ?
C3 C4 H02B 108.1 . . ?
H02A C4 H02B 107.3 . . ?
C8 C9 C10 119.5(4) . . ?
C8 C9 H021 120.2 . . ?
C10 C9 H021 120.2 . . ?
C5 C6 H02C 109.5 . . ?
C5 C6 H02D 109.5 . . ?
H02C C6 H02D 109.5 . . ?
C5 C6 H02E 109.5 . . ?
H02C C6 H02E 109.5 . . ?
H02D C6 H02E 109.5 . . ?
N3 C8 C9 121.6(4) . . ?
N3 C8 H023 119.2 . . ?
C9 C8 H023 119.2 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N2 C3 C2 -13.7(5) . . . . ?
Br01 N2 C3 C2 -157.7(3) . . . . ?
C1 N2 C3 C4 -136.4(4) . . . . ?
Br01 N2 C3 C4 79.6(5) . . . . ?
C9 C10 C11 C12 1.2(7) . . . . ?
C13 C10 C11 C12 -179.5(4) . . . . ?
C8 N3 C12 C11 -0.3(8) . . . . ?
Br02 N3 C12 C11 177.7(4) . . . . ?
C10 C11 C12 N3 -1.0(8) . . . . ?
C1 N1 C2 O2 178.5(4) . . . . ?
Br02 N1 C2 O2 3.9(7) . . . . ?
C1 N1 C2 C3 -2.6(5) . . . . ?
Br02 N1 C2 C3 -177.3(3) . . . . ?
N2 C3 C2 O2 -171.6(4) . . . . ?
C4 C3 C2 O2 -48.5(6) . . . . ?
N2 C3 C2 N1 9.5(5) . . . . ?
C4 C3 C2 N1 132.7(4) . . . . ?
C14 O4 C13 O3 1.6(7) . . . . ?
C14 O4 C13 C10 -178.0(4) . . . . ?
C11 C10 C13 O3 -11.4(7) . . . . ?
C9 C10 C13 O3 167.9(4) . . . . ?
C11 C10 C13 O4 168.2(4) . . . . ?
C9 C10 C13 O4 -12.5(6) . . . . ?
C3 N2 C1 O1 -169.9(5) . . . . ?
Br01 N2 C1 O1 -24.6(7) . . . . ?
C3 N2 C1 N1 12.7(5) . . . . ?
Br01 N2 C1 N1 158.0(3) . . . . ?
C2 N1 C1 O1 176.5(5) . . . . ?
Br02 N1 C1 O1 -8.5(7) . . . . ?
C2 N1 C1 N2 -6.0(6) . . . . ?
Br02 N1 C1 N2 169.0(3) . . . . ?
C7 C5 C4 C3 54.7(5) . . . . ?
C6 C5 C4 C3 176.6(4) . . . . ?
N2 C3 C4 C5 43.5(5) . . . . ?
C2 C3 C4 C5 -72.3(5) . . . . ?
C11 C10 C9 C8 -0.2(7) . . . . ?
C13 C10 C9 C8 -179.4(4) . . . . ?
C12 N3 C8 C9 1.4(8) . . . . ?
Br02 N3 C8 C9 -176.7(4) . . . . ?
C10 C9 C8 N3 -1.2(8) . . . . ?


# END of CIF
_chemical_name_systematic        
(N,N'-Dibromo-(S)-5-isobutylhydantoin)(methylisonicotinate)
_chemical_melting_point          370-371
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1,2-dichloroethane / Hexane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1509933'
_audit_update_record             
;
2016-10-14 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;

_audit_creation_date             2016-10-12T09:55:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C10 H10 Br2 F3 N3 O2'
_chemical_formula_sum            'C11 H10 Br2 F3 N3 O2'
_chemical_formula_weight         433.04
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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'

_cell_length_a                   9.4108(4)
_cell_length_b                   7.9826(3)
_cell_length_c                   19.9558(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.418(2)
_cell_angle_gamma                90
_cell_volume                     1486.59(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2637
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      27.38
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_crystal_density_diffrn    1.935
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    5.492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.429
_exptl_absorpt_correction_T_max  0.547

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.4737  0.7456                #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------#



#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      -0.036556
_diffrn_orient_matrix_ub_12      0.017058
_diffrn_orient_matrix_ub_13      -0.048834
_diffrn_orient_matrix_ub_21      0.094039
_diffrn_orient_matrix_ub_22      0.050199
_diffrn_orient_matrix_ub_23      -0.007464
_diffrn_orient_matrix_ub_31      0.036098
_diffrn_orient_matrix_ub_32      -0.113501
_diffrn_orient_matrix_ub_33      -0.010641
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_number            8226
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.058
_diffrn_reflns_theta_max         27.522
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.99
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.99
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.99
_reflns_Friedel_coverage         0
_reflns_number_total             3382
_reflns_number_gt                2684
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3382
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.1177
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   0.819
_refine_ls_restrained_S_all      0.819
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.65
_refine_diff_density_min         -0.801
_refine_diff_density_rms         0.254

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
F F 0.0171 0.0103 '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_
_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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6498(5) -0.0976(4) 0.0651(2) 0.0224(9) Uani 1 1 d . . . . .
C2 C 0.5650(4) 0.1175(5) 0.12592(18) 0.0189(8) Uani 1 1 d . . . . .
C3 C 0.5330(4) -0.0474(4) 0.16144(19) 0.0196(8) Uani 1 1 d . . . . .
C4 C 0.3748(5) -0.0663(5) 0.1673(2) 0.0276(9) Uani 1 1 d . . . . .
H4A H 0.3197 -0.0602 0.1222 0.041 Uiso 1 1 calc R U . . .
H4B H 0.3445 0.0239 0.1956 0.041 Uiso 1 1 calc R U . . .
H4C H 0.358 -0.1748 0.1879 0.041 Uiso 1 1 calc R U . . .
C5 C 0.6253(5) -0.0536(5) 0.2302(2) 0.0296(10) Uani 1 1 d . . . . .
H5A H 0.6143 -0.1631 0.2512 0.044 Uiso 1 1 calc R U . . .
H5B H 0.5947 0.0347 0.2593 0.044 Uiso 1 1 calc R U . . .
H5C H 0.726 -0.0364 0.2243 0.044 Uiso 1 1 calc R U . . .
C6 C 1.2183(5) 0.4421(5) 0.0658(2) 0.0281(9) Uani 1 1 d . . . . .
H6 H 1.3014 0.412 0.0461 0.034 Uiso 1 1 calc R U . . .
C7 C 1.1608(5) 0.3293(6) 0.1069(2) 0.0321(10) Uani 1 1 d . . . . .
H7 H 1.2025 0.2216 0.1147 0.039 Uiso 1 1 calc R U . . .
C8 C 1.0432(5) 0.3736(6) 0.1364(2) 0.0293(10) Uani 1 1 d . . . . .
C9 C 0.9833(5) 0.5297(6) 0.1233(2) 0.0332(10) Uani 1 1 d . . . . .
H9 H 0.9016 0.5637 0.1433 0.04 Uiso 1 1 calc R U . . .
C10 C 1.0447(5) 0.6352(5) 0.0806(2) 0.0315(10) Uani 1 1 d . . . . .
H10 H 1.0026 0.742 0.0707 0.038 Uiso 1 1 calc R U . . .
C11 C 0.9823(6) 0.2532(8) 0.1831(3) 0.0519(16) Uani 1 1 d . . . . .
N1 N 0.5824(4) -0.1669(4) 0.11389(18) 0.0267(8) Uani 1 1 d . . . . .
N2 N 0.6354(4) 0.0771(4) 0.07296(15) 0.0204(7) Uani 1 1 d . . . . .
N3 N 1.1597(4) 0.5937(4) 0.05293(16) 0.0226(7) Uani 1 1 d . . . . .
O1 O 0.7096(4) -0.1650(4) 0.02240(16) 0.0388(9) Uani 1 1 d . . . . .
O2 O 0.5346(3) 0.2556(3) 0.14456(15) 0.0277(7) Uani 1 1 d . . . . .
F1A F 1.059(4) 0.258(7) 0.2440(16) 0.102(11) Uani 0.63(9) 1 d . . P . .
F2A F 0.8543(18) 0.285(3) 0.1928(9) 0.056(5) Uani 0.63(9) 1 d . . P . .
F3A F 0.977(4) 0.097(2) 0.1588(13) 0.081(5) Uani 0.63(9) 1 d . . P . .
Br1 Br 0.57677(5) -0.39707(5) 0.12448(2) 0.02439(14) Uani 1 1 d . . . . .
Br2 Br 0.72545(4) 0.22754(5) 0.01721(2) 0.02203(14) Uani 1 1 d . . . . .
F3B F 1.084(5) 0.200(4) 0.233(2) 0.062(7) Uani 0.37(9) 1 d . . P . .
F2B F 0.867(6) 0.322(7) 0.212(4) 0.096(11) Uani 0.37(9) 1 d . . P . .
F1B F 0.946(5) 0.108(5) 0.1544(17) 0.075(11) Uani 0.37(9) 1 d . . P . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.208(5) . ?
C1 N1 1.347(5) . ?
C1 N2 1.412(4) . ?
C2 O2 1.210(4) . ?
C2 N2 1.357(5) . ?
C2 C3 1.543(5) . ?
C3 N1 1.463(5) . ?
C3 C4 1.516(6) . ?
C3 C5 1.527(6) . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 N3 1.340(5) . ?
C6 C7 1.375(6) . ?
C6 H6 0.95 . ?
C7 C8 1.365(7) . ?
C7 H7 0.95 . ?
C8 C9 1.379(6) . ?
C8 C11 1.503(6) . ?
C9 C10 1.377(6) . ?
C9 H9 0.95 . ?
C10 N3 1.320(6) . ?
C10 H10 0.95 . ?
C11 F1B 1.32(3) . ?
C11 F2A 1.27(2) . ?
C11 F1A 1.33(3) . ?
C11 F3B 1.35(4) . ?
C11 F3A 1.34(2) . ?
C11 F2B 1.41(4) . ?
N1 Br1 1.851(3) . ?
N2 Br2 1.908(3) . ?
F1A F3B 0.57(6) . ?
F2A F2B 0.49(8) . ?
F2A F1B 1.87(5) . ?
F3A F1B 0.30(6) . ?

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
_geom_angle_publ_flag
O1 C1 N1 129.3(3) . . ?
O1 C1 N2 125.3(4) . . ?
N1 C1 N2 105.4(3) . . ?
O2 C2 N2 127.9(4) . . ?
O2 C2 C3 124.6(3) . . ?
N2 C2 C3 107.4(3) . . ?
N1 C3 C4 112.5(3) . . ?
N1 C3 C5 111.7(3) . . ?
C4 C3 C5 112.2(3) . . ?
N1 C3 C2 99.3(3) . . ?
C4 C3 C2 111.8(3) . . ?
C5 C3 C2 108.6(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) . . ?
N3 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 119.4(4) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 119.1(4) . . ?
C7 C8 C11 119.8(5) . . ?
C9 C8 C11 121.1(5) . . ?
C10 C9 C8 118.4(4) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
N3 C10 C9 122.6(4) . . ?
N3 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
F1B C11 F2A 93(2) . . ?
F1B C11 F1A 120(2) . . ?
F2A C11 F1A 105(2) . . ?
F1B C11 F3B 99(2) . . ?
F2A C11 F3B 123.1(18) . . ?
F1A C11 F3B 25(3) . . ?
F1B C11 F3A 13(3) . . ?
F2A C11 F3A 104.6(15) . . ?
F1A C11 F3A 110(2) . . ?
F3B C11 F3A 88.0(17) . . ?
F1B C11 F2B 111(3) . . ?
F2A C11 F2B 20(3) . . ?
F1A C11 F2B 88.2(17) . . ?
F3B C11 F2B 109(3) . . ?
F3A C11 F2B 121(3) . . ?
F1B C11 C8 113.0(18) . . ?
F2A C11 C8 114.2(9) . . ?
F1A C11 C8 110.2(12) . . ?
F3B C11 C8 111.3(18) . . ?
F3A C11 C8 111.7(12) . . ?
F2B C11 C8 112.3(17) . . ?
C1 N1 C3 114.8(3) . . ?
C1 N1 Br1 120.9(3) . . ?
C3 N1 Br1 123.9(2) . . ?
C2 N2 C1 112.6(3) . . ?
C2 N2 Br2 127.1(2) . . ?
C1 N2 Br2 120.1(3) . . ?
C10 N3 C6 119.1(4) . . ?
F3B F1A C11 79(7) . . ?
F2B F2A C11 96(7) . . ?
F2B F2A F1B 135(8) . . ?
C11 F2A F1B 44.6(13) . . ?
F1B F3A C11 80(10) . . ?
F1A F3B C11 76(6) . . ?
F2A F2B C11 64(6) . . ?
F3A F1B C11 87(9) . . ?
F3A F1B F2A 125(10) . . ?
C11 F1B F2A 42.7(16) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C2 C3 N1 175.7(4) . . . . ?
N2 C2 C3 N1 -6.2(4) . . . . ?
O2 C2 C3 C4 56.8(5) . . . . ?
N2 C2 C3 C4 -125.1(3) . . . . ?
O2 C2 C3 C5 -67.5(5) . . . . ?
N2 C2 C3 C5 110.6(4) . . . . ?
N3 C6 C7 C8 -1.4(7) . . . . ?
C6 C7 C8 C9 1.1(7) . . . . ?
C6 C7 C8 C11 -178.1(4) . . . . ?
C7 C8 C9 C10 0.1(7) . . . . ?
C11 C8 C9 C10 179.4(4) . . . . ?
C8 C9 C10 N3 -1.3(7) . . . . ?
C7 C8 C11 F1B -57(2) . . . . ?
C9 C8 C11 F1B 123(2) . . . . ?
C7 C8 C11 F2A -161.7(11) . . . . ?
C9 C8 C11 F2A 19.1(12) . . . . ?
C7 C8 C11 F1A 80(3) . . . . ?
C9 C8 C11 F1A -99(3) . . . . ?
C7 C8 C11 F3B 53.4(19) . . . . ?
C9 C8 C11 F3B -125.8(19) . . . . ?
C7 C8 C11 F3A -43.2(19) . . . . ?
C9 C8 C11 F3A 137.6(18) . . . . ?
C7 C8 C11 F2B 177(4) . . . . ?
C9 C8 C11 F2B -3(4) . . . . ?
O1 C1 N1 C3 174.4(5) . . . . ?
N2 C1 N1 C3 -6.3(5) . . . . ?
O1 C1 N1 Br1 2.1(7) . . . . ?
N2 C1 N1 Br1 -178.7(3) . . . . ?
C4 C3 N1 C1 126.2(4) . . . . ?
C5 C3 N1 C1 -106.6(4) . . . . ?
C2 C3 N1 C1 7.8(4) . . . . ?
C4 C3 N1 Br1 -61.7(4) . . . . ?
C5 C3 N1 Br1 65.5(4) . . . . ?
C2 C3 N1 Br1 179.9(3) . . . . ?
O2 C2 N2 C1 -178.8(4) . . . . ?
C3 C2 N2 C1 3.2(5) . . . . ?
O2 C2 N2 Br2 7.0(6) . . . . ?
C3 C2 N2 Br2 -171.1(3) . . . . ?
O1 C1 N2 C2 -179.1(4) . . . . ?
N1 C1 N2 C2 1.7(5) . . . . ?
O1 C1 N2 Br2 -4.4(6) . . . . ?
N1 C1 N2 Br2 176.3(3) . . . . ?
C9 C10 N3 C6 1.1(7) . . . . ?
C7 C6 N3 C10 0.3(7) . . . . ?
F1B C11 F1A F3B 36(7) . . . . ?
F2A C11 F1A F3B 139(6) . . . . ?
F3A C11 F1A F3B 27(7) . . . . ?
F2B C11 F1A F3B 149(7) . . . . ?
C8 C11 F1A F3B -97(7) . . . . ?
F1B C11 F2A F2B 154(7) . . . . ?
F1A C11 F2A F2B 32(7) . . . . ?
F3B C11 F2A F2B 51(7) . . . . ?
F3A C11 F2A F2B 148(7) . . . . ?
C8 C11 F2A F2B -89(7) . . . . ?
F1A C11 F2A F1B -122(2) . . . . ?
F3B C11 F2A F1B -103(2) . . . . ?
F3A C11 F2A F1B -6(2) . . . . ?
F2B C11 F2A F1B -154(7) . . . . ?
C8 C11 F2A F1B 116.7(15) . . . . ?
F2A C11 F3A F1B 26(12) . . . . ?
F1A C11 F3A F1B 139(11) . . . . ?
F3B C11 F3A F1B 150(12) . . . . ?
F2B C11 F3A F1B 38(12) . . . . ?
C8 C11 F3A F1B -98(12) . . . . ?
F1B C11 F3B F1A -149(7) . . . . ?
F2A C11 F3B F1A -49(7) . . . . ?
F3A C11 F3B F1A -155(7) . . . . ?
F2B C11 F3B F1A -33(8) . . . . ?
C8 C11 F3B F1A 92(6) . . . . ?
F1B F2A F2B C11 26(6) . . . . ?
F1B C11 F2B F2A -28(7) . . . . ?
F1A C11 F2B F2A -149(7) . . . . ?
F3B C11 F2B F2A -136(6) . . . . ?
F3A C11 F2B F2A -36(7) . . . . ?
C8 C11 F2B F2A 100(6) . . . . ?
C11 F3A F1B F2A -21(8) . . . . ?
F2A C11 F1B F3A -155(11) . . . . ?
F1A C11 F1B F3A -45(13) . . . . ?
F3B C11 F1B F3A -31(12) . . . . ?
F2B C11 F1B F3A -146(11) . . . . ?
C8 C11 F1B F3A 87(11) . . . . ?
F1A C11 F1B F2A 110(2) . . . . ?
F3B C11 F1B F2A 124(2) . . . . ?
F3A C11 F1B F2A 155(11) . . . . ?
F2B C11 F1B F2A 9(3) . . . . ?
C8 C11 F1B F2A -117.8(12) . . . . ?
F2B F2A F1B F3A -7(18) . . . . ?
C11 F2A F1B F3A 31(13) . . . . ?
F2B F2A F1B C11 -38(9) . . . . ?


# END of CIF
_chemical_name_systematic        
(N,N'-Dibromo-5,5-dimethylhydantoin)(4-trifluoromethylpyridine)
_chemical_melting_point          469
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2'
