Interaction between amines and N-haloimides: a new motif for unprecedentedly short Br⋯N and I⋯N halogen bonds
Raatikainen, Kari; Rissanen, Kari; CrystEngComm 13 (2011) 6972–; doi:10.1039/c1ce05447c

data_7206787
_publ_section_title
;
 Interaction between amines and N-haloimides: a new motif for
 unprecedentedly short Br&#x22EF;N and I&#x22EF;N halogen bonds
;
_journal_issue                   23
_journal_name_full               CrystEngComm
_journal_page_first              6972
_journal_paper_doi               10.1039/c1ce05447c
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C6 H12 N4, 2(C4 H4 Br N O2)'
_chemical_formula_sum            'C14 H20 Br2 N6 O4'
_chemical_formula_weight         496.18
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      7
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2009-11-02T17:55:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 99.500(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.7065(2)
_cell_length_b                   18.5969(6)
_cell_length_c                   7.1006(2)
_cell_measurement_reflns_used    1807
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.7
_cell_measurement_theta_min      0.407
_cell_measurement_wavelength     0.71073
_cell_volume                     873.44(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.479157E-1
_diffrn_orient_matrix_UB_12      -0.43735E-2
_diffrn_orient_matrix_UB_13      -0.125611
_diffrn_orient_matrix_UB_21      -0.142125
_diffrn_orient_matrix_UB_22      -0.8545E-2
_diffrn_orient_matrix_UB_23      -0.646343E-1
_diffrn_orient_matrix_UB_31      -0.189931E-1
_diffrn_orient_matrix_UB_32      0.529087E-1
_diffrn_orient_matrix_UB_33      -0.208219E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5612
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         28.51
_diffrn_reflns_theta_min         3.11
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    4.676
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.887
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.009(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3177
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.03
_refine_ls_R_factor_gt           0.0279
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0411P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.068
_refine_ls_wR_factor_ref         0.0689
_reflns_number_gt                3031
_reflns_number_total             3177
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c1ce05447c.txt
_cod_data_source_block           HMTA-NBS
_cod_original_sg_symbol_H-M      'P n'
_cod_database_code               7206787