Halogen bonding of electrophilic bromocarbons with pseudohalide anions.
Rosokha, Sergiy V.; Stern, Charlotte L.; Swartz, Alan; Stewart, Rory; Physical chemistry chemical physics : PCCP 16 (2014) 12968–12979; doi:10.1039/c4cp00976b

data_7216145
_publ_section_title
;
 Halogen bonding of electrophilic bromocarbons with pseudohalide anions.
;
_journal_issue                   25
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              12968
_journal_page_last               12979
_journal_paper_doi               10.1039/c4cp00976b
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C Br4, C N O, C12 H28 N'
_chemical_formula_sum            'C14 H28 Br4 N2 O'
_chemical_formula_weight         560.02
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-03-04
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.504(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3579(5)
_cell_length_b                   19.0038(11)
_cell_length_c                   12.9329(7)
_cell_measurement_reflns_used    9644
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.64
_cell_measurement_theta_min      5.80
_cell_volume                     2031.6(2)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Beta test 
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.930
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Quazar optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.930
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18884
_diffrn_reflns_point_group_measured_fraction_full 0.930
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.022
_diffrn_reflns_theta_min         4.166
_diffrn_source                   microsource
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    9.673
_exptl_absorpt_correction_T_max  0.3884
_exptl_absorpt_correction_T_min  0.0614
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;

 A numerical absorption correction was applied. (XPREP, Bruker)
 Minimum and maximum transmission factors were: 0.0614 and 0.3884, respectively.

;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.831
_exptl_crystal_description       tabular
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.501
_exptl_crystal_size_mid          0.306
_exptl_crystal_size_min          0.158
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.878
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.284
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3412
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.283
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0246P)^2^+5.4056P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0723
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3411
_reflns_number_total             3412
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cp00976b2.cif
_cod_data_source_block           n2515
_cod_depositor_comments
'Adding full bibliography for 7216144--7216148.cif.'
_cod_database_code               7216145
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  {H13A,H13B} of C13, {H4A,H4B} of C4, {H3A,H3B} of C3, {H6A,H6B} of C6, {H7A,
  H7B} of C7, {H9A,H9B} of C9, {H10A,H10B} of C10, {H12A,H12B} of C12
 At 1.5 times of:
  {H14A,H14B,H14C} of C14, {H5A,H5B,H5C} of C5, {H8A,H8B,H8C} of C8, {H11A,
  H11B,H11C} of C11
2. Uiso/Uaniso restraints and constraints
Uanis(C2) - Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,
 H10B), C12(H12A,H12B), C13(H13A,H13B)
3.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C8(H8A,H8B,H8C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C)
;
_shelx_estimated_absorpt_t_max   0.310
_shelx_estimated_absorpt_t_min   0.085
_shelx_res_checksum              39231
_shelxl_version_number           2012-9