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_7216148
_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         'C2 H2 Br3 N O, 2(C N S), 2(C12 H28 N)'
_chemical_formula_sum            'C28 H58 Br3 N5 O S2'
_chemical_formula_weight         784.64
_chemical_name_systematic
;
 ?
;
_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   mixed
_audit_creation_date             2013-03-01
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.4293(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0945(3)
_cell_length_b                   11.5019(4)
_cell_length_c                   31.8838(11)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.61
_cell_measurement_theta_min      2.80
_cell_volume                     3661.9(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    'SHELXT, G.M. Sheldrick, Beta test '
_diffrn_ambient_temperature      100.03
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.925
_diffrn_measured_fraction_theta_max 0.984
_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  0.0228
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.925
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            19742
_diffrn_reflns_point_group_measured_fraction_full 0.925
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         64.916
_diffrn_reflns_theta_min         2.802
_diffrn_source                   microsource
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.359
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.5762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0679 before and 0.0339 after correction.
The Ratio of minimum to maximum transmission is 0.7656.
The \l/2 correction factor is 0.0000.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       plate
_exptl_crystal_F_000             1624
_exptl_crystal_size_max          0.528
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.024
_refine_diff_density_max         1.260
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         6113
_refine_ls_number_restraints     153
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0409P)^2^+3.9102P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0759
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5822
_reflns_number_total             6113
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cp00976b2.cif
_cod_data_source_block           n2516
_cod_depositor_comments
'Adding full bibliography for 7216144--7216148.cif.'
_cod_database_code               7216148
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  {H23C,H23D} of C23A, {H24C,H24D} of C24A, {H17A,H17B} of C17, {H18A,H18B}
  of C18, {H17C,H17D} of C17A, {H18C,H18D} of C18A, {H20A,H20B} of C20, {H21A,
  H21B} of C21, {H20C,H20D} of C20A, {H21C,H21D} of C21A, {H26A,H26B} of C26,
  {H27A,H27B} of C27, {H26C,H26D} of C26A, {H27C,H27D} of C27A, {H12A,H12B} of
  C12, {H11A,H11B} of C11, {H9A,H9B} of C9, {H8A,H8B} of C8, {H6A,H6B} of C6,
  {H5A,H5B} of C5, {H1A,H1B} of N1, {H15A,H15B} of C15, {H14A,H14B} of C14,
  {H23A,H23B} of C23, {H24A,H24B} of C24
 At 1.5 times of:
  {H16A,H16B,H16C} of C16, {H19A,H19B,H19C,H19D,H19E,H19F} of C19, {H22A,H22B,
  H22C,H22D,H22E,H22F} of C22, {H25A,H25B,H25C,H25D,H25E,H25F} of C25, {H28A,
  H28B,H28C,H28D,H28E,H28F} of C28, {H13A,H13B,H13C} of C13, {H10A,H10B,H10C}
  of C10, {H7A,H7B,H7C} of C7
2. Restrained distances
 N1-H1A - N1-H1B
 with sigma of 0.02
3. Rigid bond restraints
 C27A, C27, C26A, C26, C20A, C20, C21A, C21, C17A, C17, C18A, C18, C23A, C23,
 C24A, C24
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C27A - C27 - C26A - C26 - C20A - C20 - C21A - C21 - C17A - C17 - C18A - C18 - C23A - C23 - C24A - C24: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(C18)=Sof(H18A)=Sof(H18B)=1-Sof(H17A)=1-
 Sof(H17A)=1-Sof(H17A)=1-Sof(H17A)=1-Sof(H17A)=1-Sof(H17A)=Sof(H19A)=Sof(H19B)=
 Sof(H19C)=1-Sof(H17A)=1-Sof(H17A)=1-Sof(H17A)
 Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C21)=Sof(H21A)=Sof(H21B)=1-Sof(H20A)=1-
 Sof(H20A)=1-Sof(H20A)=1-Sof(H20A)=1-Sof(H20A)=1-Sof(H20A)=Sof(H22A)=Sof(H22B)=
 Sof(H22C)=1-Sof(H20A)=1-Sof(H20A)=1-Sof(H20A)
 Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(C24)=Sof(H24A)=Sof(H24B)=1-Sof(H23A)=1-
 Sof(H23A)=1-Sof(H23A)=1-Sof(H23A)=1-Sof(H23A)=1-Sof(H23A)=Sof(H25A)=Sof(H25B)=
 Sof(H25C)=1-Sof(H23A)=1-Sof(H23A)=1-Sof(H23A)
 Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H28A)=Sof(H28B)=
 Sof(H28C)=1-Sof(H26A)=1-Sof(H26A)=1-Sof(H26A)=1-Sof(H26A)=1-Sof(H26A)=1-
 Sof(H26A)=1-Sof(H26A)=1-Sof(H26A)=1-Sof(H26A)
6.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C12(H12A,
 H12B), C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B),
 C17A(H17C,H17D), C18A(H18C,H18D), C20(H20A,H20B), C21(H21A,H21B), C20A(H20C,
 H20D), C21A(H21C,H21D), C23(H23A,H23B), C24(H24A,H24B), C23A(H23C,H23D),
 C24A(H24C,H24D), C26(H26A,H26B), C27(H27A,H27B), C26A(H26C,H26D), C27A(H27C,
 H27D)
6.b Me refined with riding coordinates:
 C19(H19A,H19B,H19C), C19(H19D,H19E,H19F), C22(H22A,H22B,H22C), C22(H22D,H22E,
 H22F), C25(H25A,H25B,H25C), C25(H25D,H25E,H25F), C28(H28A,H28B,H28C), C28(H28D,
 H28E,H28F)
6.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C16(H16A,H16B,H16C)
;
_shelx_estimated_absorpt_t_max   0.882
_shelx_estimated_absorpt_t_min   0.164
_shelx_res_checksum              33167
_shelxl_version_number           2012-9