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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/7/12/18/7121885.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_7121885
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, C2 H2 Br3 N O'
_chemical_formula_sum            'C8 H14 Br3 N3 O'
_chemical_formula_weight         407.95
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 92.369(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4062(4)
_cell_length_b                   20.4294(14)
_cell_length_c                   9.5955(6)
_cell_measurement_reflns_used    7036
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.7185
_cell_measurement_theta_min      2.9124
_cell_volume                     1254.74(14)
_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 0.974
_diffrn_measured_fraction_theta_max 0.928
_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  0.0712
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12541
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.573
_diffrn_reflns_theta_min         2.914
_diffrn_source                   'sealed tube X-ray source'
_exptl_absorpt_coefficient_mu    9.625
_exptl_absorpt_correction_T_max  0.7475
_exptl_absorpt_correction_T_min  0.4550
_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    2.160
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.050
_refine_diff_density_max         2.297
_refine_diff_density_min         -1.416
_refine_diff_density_rms         0.298
_refine_ls_extinction_coef       0.0062(9)
_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   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         3269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0493
_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)+(0.0883P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1380
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2726
_reflns_number_total             3269
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc04629h2.cif
_cod_data_source_block           RS_13_0m-combined
_cod_depositor_comments
'Adding full bibliography for 7121885--7121891.cif.'
_cod_database_code               7121885
_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   0.101
_shelx_estimated_absorpt_t_max   0.645
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C1 C -0.0150(9) 0.1741(3) 0.7209(6) 0.0245(13) Uani 1 1 d . .
H1A H 0.125606 0.169888 0.682636 0.029 Uiso 1 1 calc R U
H1B H -0.011684 0.211539 0.786504 0.029 Uiso 1 1 calc R U
C2 C -0.1763(8) 0.1881(3) 0.6003(5) 0.0160(10) Uani 1 1 d . .
H2A H -0.238006 0.232066 0.612383 0.019 Uiso 1 1 calc R U
H2B H -0.106448 0.187366 0.510240 0.019 Uiso 1 1 calc R U
C3 C -0.2714(8) 0.1216(3) 0.8541(5) 0.0204(12) Uani 1 1 d . .
H3C H -0.267660 0.156832 0.924900 0.024 Uiso 1 1 calc R U
H3D H -0.309947 0.080266 0.900529 0.024 Uiso 1 1 calc R U
C4 C -0.4382(8) 0.1382(3) 0.7364(5) 0.0195(12) Uani 1 1 d . .
H4A H -0.551971 0.105374 0.736395 0.023 Uiso 1 1 calc R U
H4B H -0.499360 0.181719 0.754128 0.023 Uiso 1 1 calc R U
C5 C -0.0723(9) 0.0605(3) 0.6940(5) 0.0218(12) Uani 1 1 d . .
H5A H -0.101241 0.018925 0.742440 0.026 Uiso 1 1 calc R U
H5B H 0.064824 0.056421 0.650840 0.026 Uiso 1 1 calc R U
C6 C -0.2447(9) 0.0730(3) 0.5789(5) 0.0201(12) Uani 1 1 d . .
H6A H -0.183037 0.071387 0.486040 0.024 Uiso 1 1 calc R U
H6B H -0.352715 0.038494 0.582416 0.024 Uiso 1 1 calc R U
C7 C 0.2641(7) 0.1338(3) 1.1761(5) 0.0100(9) Uani 1 1 d . .
C8 C 0.3508(7) 0.0723(3) 1.1030(4) 0.0104(9) Uani 1 1 d . .
N1 N -0.0642(6) 0.1146(2) 0.7959(4) 0.0124(8) Uani 1 1 d . .
N2 N -0.3419(6) 0.1382(2) 0.5997(4) 0.0137(9) Uani 1 1 d . .
N3 N 0.2554(6) 0.0555(2) 0.9824(4) 0.0099(8) Uani 1 1 d . .
H3A H 0.301906 0.022080 0.934740 0.012 Uiso 1 1 calc R U
H3B H 0.145945 0.077671 0.950452 0.012 Uiso 1 1 calc R U
Br1 Br 0.31065(7) 0.20879(3) 1.05682(4) 0.01319(16) Uani 1 1 d . .
Br2 Br -0.03463(7) 0.12335(3) 1.20208(4) 0.01338(17) Uani 1 1 d . .
Br3 Br 0.40877(7) 0.14501(3) 1.35708(4) 0.01363(17) Uani 1 1 d . .
O1 O 0.5047(5) 0.04410(19) 1.1555(3) 0.0150(8) Uani 1 1 d . .
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'
N N 0.0061 0.0033 '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'
O O 0.0106 0.0060 '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
N1 C1 C2 111.9(4)
N1 C1 H1A 109.2
C2 C1 H1A 109.2
N1 C1 H1B 109.2
C2 C1 H1B 109.2
H1A C1 H1B 107.9
N2 C2 C1 109.6(4)
N2 C2 H2A 109.8
C1 C2 H2A 109.8
N2 C2 H2B 109.8
C1 C2 H2B 109.8
H2A C2 H2B 108.2
N1 C3 C4 110.4(4)
N1 C3 H3C 109.6
C4 C3 H3C 109.6
N1 C3 H3D 109.6
C4 C3 H3D 109.6
H3C C3 H3D 108.1
N2 C4 C3 110.2(4)
N2 C4 H4A 109.6
C3 C4 H4A 109.6
N2 C4 H4B 109.6
C3 C4 H4B 109.6
H4A C4 H4B 108.1
N1 C5 C6 110.7(4)
N1 C5 H5A 109.5
C6 C5 H5A 109.5
N1 C5 H5B 109.5
C6 C5 H5B 109.5
H5A C5 H5B 108.1
N2 C6 C5 110.0(4)
N2 C6 H6A 109.7
C5 C6 H6A 109.7
N2 C6 H6B 109.7
C5 C6 H6B 109.7
H6A C6 H6B 108.2
C8 C7 Br1 107.8(3)
C8 C7 Br3 109.4(3)
Br1 C7 Br3 110.7(2)
C8 C7 Br2 109.9(3)
Br1 C7 Br2 109.7(2)
Br3 C7 Br2 109.4(2)
O1 C8 N3 124.4(5)
O1 C8 C7 119.3(4)
N3 C8 C7 116.3(4)
C1 N1 C3 109.0(4)
C1 N1 C5 107.5(5)
C3 N1 C5 108.5(4)
C2 N2 C4 109.0(4)
C2 N2 C6 108.4(4)
C4 N2 C6 108.2(4)
C8 N3 H3A 120.0
C8 N3 H3B 120.0
H3A N3 H3B 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.455(7)
C1 C2 1.545(6)
C1 H1A 0.9900
C1 H1B 0.9900
C2 N2 1.471(7)
C2 H2A 0.9900
C2 H2B 0.9900
C3 N1 1.468(7)
C3 C4 1.559(6)
C3 H3C 0.9900
C3 H3D 0.9900
C4 N2 1.472(7)
C4 H4A 0.9900
C4 H4B 0.9900
C5 N1 1.475(7)
C5 C6 1.551(7)
C5 H5A 0.9900
C5 H5B 0.9900
C6 N2 1.487(7)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.553(7)
C7 Br1 1.943(5)
C7 Br3 1.948(4)
C7 Br2 1.952(5)
C8 O1 1.232(6)
C8 N3 1.331(5)
N3 H3A 0.8800
N3 H3B 0.8800
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 2.7(7)
N1 C3 C4 N2 3.4(7)
N1 C5 C6 N2 3.8(7)
Br1 C7 C8 O1 112.8(4)
Br3 C7 C8 O1 -7.7(6)
Br2 C7 C8 O1 -127.8(4)
Br1 C7 C8 N3 -64.6(5)
Br3 C7 C8 N3 175.0(3)
Br2 C7 C8 N3 54.9(5)
C2 C1 N1 C3 -59.8(6)
C2 C1 N1 C5 57.7(6)
C4 C3 N1 C1 55.8(6)
C4 C3 N1 C5 -60.9(6)
C6 C5 N1 C1 -60.9(6)
C6 C5 N1 C3 56.8(6)
C1 C2 N2 C4 57.1(6)
C1 C2 N2 C6 -60.4(5)
C3 C4 N2 C2 -60.5(6)
C3 C4 N2 C6 57.1(6)
C5 C6 N2 C2 56.8(5)
C5 C6 N2 C4 -61.3(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139188824
