From charge transfer to electron transfer in halogen-bonded complexes of electrophilic bromocarbons with halide anions.
Rosokha, Sergiy V.; Traversa, Alfredo; Physical chemistry chemical physics : PCCP 17 (2015) 4989–4999; doi:10.1039/c4cp05220j

data_7219329
_publ_section_title
;
 From charge transfer to electron transfer in halogen-bonded complexes of
 electrophilic bromocarbons with halide anions.
;
_journal_issue                   7
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              4989
_journal_page_last               4999
_journal_paper_doi               10.1039/c4cp05220j
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'I, C Br3 F, C12 H28 N'
_chemical_formula_sum            'C13 H28 Br3 F I N'
_chemical_formula_weight         583.99
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-03-14
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_audit_update_record
;
2014-09-28 deposited with the CCDC.
2015-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   33.76(3)
_cell_length_b                   8.427(6)
_cell_length_c                   14.421(11)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.534
_cell_measurement_theta_min      2.809
_cell_volume                     4103(6)
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.92
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0866
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            121246
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.066
_diffrn_reflns_theta_min         2.413
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    7.405
_exptl_absorpt_correction_T_max  0.7044
_exptl_absorpt_correction_T_min  0.6379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1184 before and 0.1022 after correction.
The Ratio of minimum to maximum transmission is 0.9056.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.891
_exptl_crystal_description       columnar
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.163
_refine_diff_density_max         0.994
_refine_diff_density_min         -0.830
_refine_diff_density_rms         0.130
_refine_ls_abs_structure_details
;
 Flack x determined using 4925 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.041(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         11920
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0283
_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^)+(0.0150P)^2^+3.5229P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0578
_refine_ls_wR_factor_ref         0.0596
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                10976
_reflns_number_total             11920
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cp05220j2.cif
_cod_data_source_block           n3382
_cod_depositor_comments
'Adding full bibliography for 7219328--7219330.cif.'
_cod_original_cell_volume        4102(5)
_cod_database_code               7219329
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.378
_shelx_estimated_absorpt_t_min   0.300
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.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), C15(H15A,H15B), C16(H16A,H16B),
 C18(H18A,H18B), C19(H19A,H19B), C21(H21A,H21B), C22(H22A,H22B), C24(H24A,H24B),
  C25(H25A,H25B)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C8(H8A,H8B,H8C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C),
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C23(H23A,H23B,H23C), C26(H26A,H26B,
 H26C)
;
_shelx_res_checksum              26594
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'