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#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/18/7121889.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7121889
loop_
_publ_author_name
'Weinberger, Craig'
'Hines, Rachel'
'Zeller, Matthias'
'Rosokha, Sergiy V.'
_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_formula_moiety         'C6 H12 N2, C Br Cl3'
_chemical_formula_sum            'C7 H12 Br Cl3 N2'
_chemical_formula_weight         310.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-05-17 deposited with the CCDC.
2018-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.625(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8771(3)
_cell_length_b                   16.4201(9)
_cell_length_c                   11.9239(6)
_cell_measurement_reflns_used    9917
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.3347
_cell_measurement_theta_min      3.0304
_cell_volume                     1130.96(10)
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_collection       'Apex3 v2016.9-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_refinement
;  
SHELXL-2016/6 (Sheldrick, 2015, 2016), 
SHELXLE Rev714 (Hübschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23547
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.137
_diffrn_reflns_theta_min         3.029
_diffrn_source                   'sealed tube X-ray source'
_exptl_absorpt_coefficient_mu    4.301
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.4983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       0.0069(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         4405
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0379
_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/[σ²(Fo²)+1.8115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0562
_refine_ls_wR_factor_ref         0.0625
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3439
_reflns_number_total             4405
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc04629h2.cif
_cod_data_source_block           RS_12_0m
_cod_depositor_comments
'Adding full bibliography for 7121885--7121891.cif.'
_cod_database_code               7121889
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.278
_shelx_estimated_absorpt_t_max   0.480
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1405(3) -0.04122(12) 0.15105(17) 0.0145(4) Uani 1 1 d . . . . .
H1A H -0.103335 -0.070366 0.084023 0.017 Uiso 1 1 calc R U . A 2
H1B H -0.311105 -0.038231 0.142511 0.017 Uiso 1 1 calc R U . A 2
C2 C -0.0392(3) -0.08867(12) 0.26152(17) 0.0152(4) Uani 1 1 d . . . . .
H2A H -0.166034 -0.105021 0.301069 0.018 Uiso 1 1 calc R U . B 2
H2B H 0.038754 -0.138679 0.241657 0.018 Uiso 1 1 calc R U . B 2
C3 C 0.2102(3) 0.03571(12) 0.16716(17) 0.0140(4) Uani 1 1 d . . . . .
H3A H 0.278977 0.090902 0.170858 0.017 Uiso 1 1 calc R U . C 2
H3B H 0.248716 0.007509 0.099697 0.017 Uiso 1 1 calc R U . C 2
C4 C 0.3125(3) -0.01231(13) 0.27685(18) 0.0152(4) Uani 1 1 d . . . . .
H4A H 0.394936 -0.061087 0.256280 0.018 Uiso 1 1 calc R U . D 2
H4B H 0.425715 0.022286 0.327344 0.018 Uiso 1 1 calc R U . D 2
C5 C -0.0953(3) 0.08380(12) 0.25695(17) 0.0156(4) Uani 1 1 d . . . . .
H5A H -0.265044 0.088734 0.250547 0.019 Uiso 1 1 calc R U . E 2
H5B H -0.028792 0.139366 0.261513 0.019 Uiso 1 1 calc R U . E 2
C6 C 0.0068(4) 0.03584(13) 0.36656(17) 0.0170(4) Uani 1 1 d . . . . .
H6A H 0.116183 0.070994 0.418256 0.020 Uiso 1 1 calc R U . F 2
H6B H -0.119418 0.019915 0.406789 0.020 Uiso 1 1 calc R U . F 2
C7 C 0.4761(4) 0.250000 0.4561(2) 0.0106(5) Uani 1 2 d DS T P . .
C8 C 0.5392(4) 0.250000 0.9472(2) 0.0105(5) Uani 1 2 d DS T P . .
Br1 Br 0.6414(4) 0.15563(17) 0.52765(19) 0.0100(2) Uani 0.5 1 d . . P G 1
Br2 Br 0.7104(3) 0.15765(14) 1.01943(13) 0.01061(19) Uani 0.5 1 d . . P H 1
Cl1 Cl 0.6237(11) 0.1599(4) 0.5122(5) 0.0100(2) Uani 0.5 1 d D . P G 2
Cl2 Cl 0.6883(8) 0.1591(4) 1.0009(4) 0.01061(19) Uani 0.5 1 d D . P H 2
Cl3 Cl 0.46069(12) 0.250000 0.30582(6) 0.01710(14) Uani 1 2 d DS T P G 2
Cl4 Cl 0.18989(11) 0.250000 0.48549(6) 0.01645(14) Uani 1 2 d DS T P G 2
Cl5 Cl 0.51679(12) 0.250000 0.79700(6) 0.01825(14) Uani 1 2 d DS T P H 2
Cl6 Cl 0.25563(11) 0.250000 0.98024(6) 0.01647(14) Uani 1 2 d DS T P H 2
N1 N -0.0432(3) 0.04212(10) 0.15562(14) 0.0124(3) Uani 1 1 d . . . I 2
N2 N 0.1281(3) -0.03748(10) 0.33790(14) 0.0113(3) Uani 1 1 d . . . J 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 C1 C2 110.34(15) . .
N1 C1 H1A 109.6 . .
C2 C1 H1A 109.6 . .
N1 C1 H1B 109.6 . .
C2 C1 H1B 109.6 . .
H1A C1 H1B 108.1 . .
N2 C2 C1 110.25(15) . .
N2 C2 H2A 109.6 . .
C1 C2 H2A 109.6 . .
N2 C2 H2B 109.6 . .
C1 C2 H2B 109.6 . .
H2A C2 H2B 108.1 . .
N1 C3 C4 110.07(15) . .
N1 C3 H3A 109.6 . .
C4 C3 H3A 109.6 . .
N1 C3 H3B 109.6 . .
C4 C3 H3B 109.6 . .
H3A C3 H3B 108.2 . .
N2 C4 C3 110.70(14) . .
N2 C4 H4A 109.5 . .
C3 C4 H4A 109.5 . .
N2 C4 H4B 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 108.1 . .
N1 C5 C6 110.50(15) . .
N1 C5 H5A 109.6 . .
C6 C5 H5A 109.6 . .
N1 C5 H5B 109.6 . .
C6 C5 H5B 109.6 . .
H5A C5 H5B 108.1 . .
N2 C6 C5 110.42(16) . .
N2 C6 H6A 109.6 . .
C5 C6 H6A 109.6 . .
N2 C6 H6B 109.6 . .
C5 C6 H6B 109.6 . .
H6A C6 H6B 108.1 . .
Cl3 C7 Cl4 108.91(13) . .
Cl3 C7 Cl1 108.0(2) . .
Cl4 C7 Cl1 109.8(3) . .
Cl1 C7 Cl1 112.3(5) 4_565 .
Br1 C7 Br1 105.94(19) 4_565 .
Cl5 C8 Cl6 108.99(13) . .
Cl5 C8 Cl2 107.6(2) . 4_565
Cl6 C8 Cl2 109.7(2) . 4_565
Cl5 C8 Cl2 107.6(2) . .
Cl6 C8 Cl2 109.7(2) . .
Cl2 C8 Cl2 113.1(4) 4_565 .
Br2 C8 Br2 103.38(16) . 4_565
C5 N1 C3 108.46(15) . .
C5 N1 C1 108.85(16) . .
C3 N1 C1 108.33(15) . .
C6 N2 C4 108.52(15) . .
C6 N2 C2 108.28(15) . .
C4 N2 C2 108.83(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.480(2) .
C1 C2 1.552(3) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 N2 1.474(2) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 N1 1.473(2) .
C3 C4 1.551(3) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 N2 1.472(2) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 N1 1.469(3) .
C5 C6 1.549(3) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 N2 1.471(3) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 Cl3 1.778(3) .
C7 Cl4 1.780(3) .
C7 Cl1 1.783(6) 4_565
C7 Cl1 1.783(6) .
C7 Br1 1.941(3) 4_565
C7 Br1 1.941(3) .
C8 Cl5 1.771(3) .
C8 Cl6 1.782(2) .
C8 Cl2 1.788(5) 4_565
C8 Cl2 1.788(5) .
C8 Br2 1.933(2) .
C8 Br2 1.933(2) 4_565
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N1 C1 C2 N2 -1.1(2)
N1 C3 C4 N2 -0.1(2)
N1 C5 C6 N2 0.4(2)
C6 C5 N1 C3 -59.3(2)
C6 C5 N1 C1 58.35(19)
C4 C3 N1 C5 59.0(2)
C4 C3 N1 C1 -59.0(2)
C2 C1 N1 C5 -57.94(19)
C2 C1 N1 C3 59.8(2)
C5 C6 N2 C4 58.4(2)
C5 C6 N2 C2 -59.5(2)
C3 C4 N2 C6 -58.6(2)
C3 C4 N2 C2 59.0(2)
C1 C2 N2 C6 59.7(2)
C1 C2 N2 C4 -58.0(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139188826
