Dibromohydantoins as halogen bond (XB) donors: a route toward the introduction of chirality in halogen bonded systems
Nicolas, Irène; Jeannin, Olivier; Pichon, Delphine; Fourmigué, Marc; CrystEngComm 18 (2016) 9325–; doi:10.1039/C6CE02175A

data_7227009
_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         'C12 H13 Br2 N3 O4'
_chemical_formula_sum            'C12 H13 Br2 N3 O4'
_chemical_formula_weight         423.07
_chemical_melting_point          407
_chemical_name_systematic
(N,N'-Dibromo-5,5-dimethylhydantoin)(methylisonicotinate)
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'iterative - e.g. charge flipping method'
_atom_sites_solution_secondary   'iterative - e.g. charge flipping method'
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2016-10-12T09:39:17-00:00
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_audit_update_record
;
2016-10-14 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;
_cell_angle_alpha                88.236(5)
_cell_angle_beta                 81.458(5)
_cell_angle_gamma                85.411(5)
_cell_formula_units_Z            2
_cell_length_a                   6.1692(8)
_cell_length_b                   7.9700(10)
_cell_length_c                   15.743(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                     762.88(17)
_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 0.991
_diffrn_measured_fraction_theta_max 0.976
_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  0.0368
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_Laue_measured_fraction_full 0.991
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_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
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_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5692
_diffrn_reflns_point_group_measured_fraction_full 0.991
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.578
_diffrn_reflns_theta_min         2.617
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.331
_exptl_absorpt_correction_T_max  0.726
_exptl_absorpt_correction_T_min  0.116
_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    1.842
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chlorobenzene / Hexane'
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.422
_refine_diff_density_min         -1.173
_refine_diff_density_rms         0.209
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
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_refine_ls_number_reflns         3446
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.072
_refine_ls_R_factor_gt           0.0559
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1190P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1645
_refine_ls_wR_factor_ref         0.1774
_reflns_Friedel_coverage         0
_reflns_number_gt                2684
_reflns_number_total             3446
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce02175a1.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7227007--7227011.cif.'
_cod_original_cell_volume        762.90(17)
_cod_database_code               7227009
_shelx_res_checksum              62827