Resolving the halogen vs. hydrogen bonding dichotomy in solutions: intermolecular complexes of trihalomethanes with halide and pseudohalide anions.
Watson, Brandon; Grounds, Olivia; Borley, William; Rosokha, Sergiy V.; Physical chemistry chemical physics : PCCP 20 (2018) 21999–22007; doi:10.1039/c8cp03505a

data_7231317
_publ_section_title
;
 Resolving the halogen vs. hydrogen bonding dichotomy in solutions:
 intermolecular complexes of trihalomethanes with halide and pseudohalide
 anions.
;
_journal_issue                   34
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              21999
_journal_page_last               22007
_journal_paper_doi               10.1039/c8cp03505a
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C12 H28 N, C H I3, Br'
_chemical_formula_sum            'C13 H29 Br I3 N'
_chemical_formula_weight         659.98
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_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
_audit_creation_date             2014-05-20
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2018-04-17 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.065(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.7748(6)
_cell_length_b                   8.9163(7)
_cell_length_c                   13.3043(10)
_cell_measurement_reflns_used    9972
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.664
_cell_measurement_theta_min      2.759
_cell_volume                     1030.62(13)
_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      99.98
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_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  0.0624
_diffrn_reflns_av_unetI/netI     0.0893
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9213
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.030
_diffrn_reflns_theta_min         2.621
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    6.477
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1254 before and 0.0869 after correction.
The Ratio of minimum to maximum transmission is 0.5746.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.127
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.492
_refine_diff_density_min         -1.364
_refine_diff_density_rms         0.273
_refine_ls_abs_structure_details
;
 Flack x determined using 2231 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         5325
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0774P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1336
_reflns_Friedel_coverage         0.785
_reflns_Friedel_fraction_full    0.863
_reflns_Friedel_fraction_max     0.776
_reflns_number_gt                5206
_reflns_number_total             5325
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cp03505a2.cif
_cod_data_source_block           n3540
_cod_depositor_comments
'Adding full bibliography for 7231317--7231319.cif.'
_cod_database_code               7231317
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.782
_shelx_estimated_absorpt_t_min   0.243
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B),
 C11(H11A,H11B), C12(H12A,H12B)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C7(H7A,H7B,H7C), C10(H10A,H10B,H10C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              15984