Continuum of covalent to intermolecular bonding in the halogen-bonded complexes of 1,4-diazabicyclo[2.2.2]octane with bromine-containing electrophiles.
Weinberger, Craig; Hines, Rachel; Zeller, Matthias; Rosokha, Sergiy V.; Chemical communications (Cambridge, England) 54 (2018) 8060–8063; doi:10.1039/c8cc04629h

data_7121887
_publ_section_title
;
 Continuum of covalent to intermolecular bonding in the halogen-bonded
 complexes of 1,4-diazabicyclo[2.2.2]octane with bromine-containing
 electrophiles.
;
_journal_issue                   58
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8060
_journal_page_last               8063
_journal_paper_doi               10.1039/c8cc04629h
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C6 H12 N2, Br3 C N O2, C H Cl3'
_chemical_formula_sum            'C8 H13 Br3 Cl3 N3 O2'
_chemical_formula_weight         529.29
_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             2015-07-10
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2018-05-17 deposited with the CCDC.
2018-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.314(2)
_cell_length_b                   18.260(3)
_cell_length_c                   6.4262(10)
_cell_measurement_reflns_used    9864
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.066
_cell_measurement_theta_min      3.924
_cell_volume                     1679.6(4)
_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, 2015)'
_diffrn_ambient_temperature      99.96
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.994
_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  0.0495
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.944
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9754
_diffrn_reflns_point_group_measured_fraction_full 0.855
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.061
_diffrn_reflns_theta_min         4.844
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    13.331
_exptl_absorpt_correction_T_max  0.1621
_exptl_absorpt_correction_T_min  0.0447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1320 before and 0.0665 after correction.
The Ratio of minimum to maximum transmission is 0.2758.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.093
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.436
_exptl_crystal_size_mid          0.385
_exptl_crystal_size_min          0.246
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.118
_refine_ls_abs_structure_details
;
 Flack x determined using 1023 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.09(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2603
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0304
_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^)+(0.0403P)^2^+1.4290P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0768
_reflns_Friedel_coverage         0.652
_reflns_Friedel_fraction_full    0.746
_reflns_Friedel_fraction_max     0.789
_reflns_number_gt                2596
_reflns_number_total             2603
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc04629h2.cif
_cod_data_source_block           cx0500
_cod_depositor_comments
'Adding full bibliography for 7121885--7121891.cif.'
_cod_original_cell_volume        1679.6(5)
_cod_database_code               7121887
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.138
_shelx_estimated_absorpt_t_min   0.068
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
;
_shelx_res_checksum              26893
_shelx_hkl_checksum              86231
_olex2_date_sample_data_collection 2015-07-09
_olex2_date_sample_submission    2015-07-08
_olex2_submission_original_sample_id cx0500
_olex2_submission_special_instructions 'No special instructions were received'