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#$Date: 2023-04-20 14:53:48 +0300 (Thu, 20 Apr 2023) $
#$Revision: 282777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/55/1545579.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_1545579
loop_
_publ_author_name
'Rosokha, Sergiy V.'
_publ_section_title
;
 Electron-transfer reactions of halogenated electrophiles: a different
 look into the nature of halogen bonding
;
_journal_name_full               'Faraday Discussions'
_journal_page_first              315
_journal_page_last               332
_journal_paper_doi               10.1039/C7FD00074J
_journal_volume                  203
_journal_year                    2017
_chemical_formula_moiety         '4(C2 H2 Br3 N O), C10 H16 N2'
_chemical_formula_sum            'C18 H24 Br12 N6 O4'
_chemical_formula_weight         1347.35
_chemical_name_systematic
;
 ?
;
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2013-04-03
_audit_creation_method
;
  Olex2 1.2
  (compiled Mar 21 2013 11:17:50, GUI svn.r4446)
;
_audit_update_record
;
2017-02-11 deposited with the CCDC.
2017-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.4347(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.0422(3)
_cell_length_b                   5.94620(10)
_cell_length_c                   20.4996(4)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.46
_cell_measurement_theta_min      2.39
_cell_volume                     1708.60(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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            25906
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.543
_diffrn_reflns_theta_min         1.453
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    14.102
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0875 before and 0.0499 after correction.
The Ratio of minimum to maximum transmission is 0.7075.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.619
_exptl_crystal_description       needle
_exptl_crystal_F_000             1252
_exptl_crystal_size_max          0.565
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.017
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         5190
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0221
_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/[σ²(Fo²)+(0.0343P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0513
_refine_ls_wR_factor_ref         0.0674
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4318
_reflns_number_total             5190
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7fd00074j2.cif
_cod_data_source_block           n2628
_cod_database_code               1545579
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H) groups, All N(H,H) groups
;
_shelx_estimated_absorpt_t_max   0.796
_shelx_estimated_absorpt_t_min   0.046
_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.
;
_shelxl_version_number           2012-9
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_adp
Br1 Br 0.22770(2) 0.83719(5) 0.71529(2) 0.01859(7) Uani 1 1 d .
Br2 Br 0.22366(2) 0.78612(5) 0.56284(2) 0.01652(7) Uani 1 1 d .
Br3 Br 0.34367(2) 0.44488(5) 0.65586(2) 0.01622(7) Uani 1 1 d .
O1 O 0.42813(14) 0.9126(4) 0.58424(9) 0.0173(4) Uani 1 1 d .
N1 N 0.43273(18) 0.9791(4) 0.69310(11) 0.0130(5) Uani 1 1 d .
H1A H 0.412(2) 0.966(6) 0.7288(16) 0.016 Uiso 1 1 d U
H1B H 0.484(2) 1.059(6) 0.6903(15) 0.016 Uiso 1 1 d U
C1 C 0.30175(19) 0.7527(5) 0.64249(12) 0.0113(5) Uani 1 1 d .
C2 C 0.39435(19) 0.8926(5) 0.63781(13) 0.0121(5) Uani 1 1 d .
Br4 Br 0.67320(2) 0.78655(5) 0.67204(2) 0.01408(7) Uani 1 1 d .
Br5 Br 0.65946(2) 0.70855(5) 0.52083(2) 0.01509(7) Uani 1 1 d .
Br6 Br 0.80376(2) 0.41486(5) 0.61098(2) 0.01092(6) Uani 1 1 d .
O2 O 0.58180(14) 0.3292(3) 0.67077(9) 0.0143(4) Uani 1 1 d .
N2 N 0.57366(19) 0.2588(4) 0.56248(12) 0.0152(5) Uani 1 1 d .
H2A H 0.544(2) 0.142(6) 0.5641(15) 0.018 Uiso 1 1 d U
H2B H 0.596(2) 0.285(6) 0.5257(16) 0.018 Uiso 1 1 d U
C3 C 0.67797(19) 0.5608(5) 0.60461(12) 0.0115(5) Uani 1 1 d .
C4 C 0.60448(18) 0.3726(5) 0.61515(13) 0.0113(5) Uani 1 1 d .
N3 N 0.97727(17) 0.2098(4) 0.62236(11) 0.0142(5) Uani 1 1 d .
C5 C 0.99014(18) 0.1051(5) 0.56127(12) 0.0115(5) Uani 1 1 d .
C6 C 0.9401(2) -0.0898(5) 0.54358(14) 0.0156(6) Uani 1 1 d .
H6 H 0.901(2) -0.148(6) 0.5711(15) 0.019 Uiso 1 1 d U
C7 C 1.0502(2) 0.1932(5) 0.51610(14) 0.0158(6) Uani 1 1 d .
H7 H 1.082(2) 0.323(6) 0.5248(15) 0.019 Uiso 1 1 d U
C8 C 0.9618(2) 0.0589(6) 0.67662(15) 0.0187(6) Uani 1 1 d .
H8A H 0.903(2) -0.028(6) 0.6690(16) 0.022 Uiso 1 1 d U
H8B H 0.957(2) 0.133(6) 0.7182(16) 0.022 Uiso 1 1 d U
H8C H 1.016(2) -0.038(6) 0.6826(16) 0.022 Uiso 1 1 d U
C9 C 1.0441(2) 0.3908(6) 0.64053(16) 0.0216(7) Uani 1 1 d .
H9A H 1.039(2) 0.520(6) 0.6058(17) 0.026 Uiso 1 1 d U
H9B H 1.028(2) 0.454(6) 0.6852(17) 0.026 Uiso 1 1 d U
H9C H 1.102(3) 0.346(6) 0.6460(16) 0.026 Uiso 1 1 d U
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'
N N 0.0061 0.0033 '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
_geom_angle_site_symmetry_1
H1A N1 H1B 117(3) .
C2 N1 H1A 126(2) .
C2 N1 H1B 117(2) .
Br1 C1 Br3 108.00(13) .
Br2 C1 Br1 108.82(13) .
Br2 C1 Br3 111.79(13) .
C2 C1 Br1 113.53(18) .
C2 C1 Br2 109.24(17) .
C2 C1 Br3 105.48(18) .
O1 C2 N1 124.5(3) .
O1 C2 C1 118.5(2) .
N1 C2 C1 117.0(2) .
H2A N2 H2B 114(3) .
C4 N2 H2A 123(2) .
C4 N2 H2B 121(2) .
Br4 C3 Br5 108.15(13) .
Br4 C3 Br6 109.20(12) .
Br5 C3 Br6 109.40(13) .
C4 C3 Br4 110.56(17) .
C4 C3 Br5 113.45(17) .
C4 C3 Br6 106.01(17) .
O2 C4 N2 123.9(3) .
O2 C4 C3 119.6(2) .
N2 C4 C3 116.4(2) .
C5 N3 C8 115.9(2) .
C5 N3 C9 115.7(2) .
C8 N3 C9 112.5(2) .
C6 C5 N3 120.4(2) .
C7 C5 N3 122.4(3) .
C7 C5 C6 117.2(2) .
C5 C6 H6 119(2) .
C7 C6 C5 121.7(3) 3_756
C7 C6 H6 119(2) 3_756
C5 C7 H7 120(2) .
C6 C7 C5 121.1(3) 3_756
C6 C7 H7 119(2) 3_756
N3 C8 H8A 111.5(19) .
N3 C8 H8B 114(2) .
N3 C8 H8C 108(2) .
H8A C8 H8B 106(3) .
H8A C8 H8C 111(3) .
H8B C8 H8C 105(3) .
N3 C9 H9A 110.6(19) .
N3 C9 H9B 109(2) .
N3 C9 H9C 113(2) .
H9A C9 H9B 109(3) .
H9A C9 H9C 110(3) .
H9B C9 H9C 105(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.936(3) .
Br2 C1 1.922(3) .
Br3 C1 1.937(3) .
O1 C2 1.228(3) .
N1 H1A 0.81(3) .
N1 H1B 0.87(3) .
N1 C2 1.329(3) .
C1 C2 1.552(4) .
Br4 C3 1.931(3) .
Br5 C3 1.933(2) .
Br6 C3 1.965(3) .
O2 C4 1.229(3) .
N2 H2A 0.81(4) .
N2 H2B 0.85(3) .
N2 C4 1.325(3) .
C3 C4 1.546(4) .
N3 C5 1.420(3) .
N3 C8 1.455(4) .
N3 C9 1.461(4) .
C5 C6 1.392(4) .
C5 C7 1.392(4) .
C6 H6 0.88(3) .
C6 C7 1.383(4) 3_756
C7 C6 1.383(4) 3_756
C7 H7 0.90(3) .
C8 H8A 0.98(4) .
C8 H8B 0.97(3) .
C8 H8C 0.96(3) .
C9 H9A 1.05(4) .
C9 H9B 1.03(3) .
C9 H9C 0.85(4) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O2 0.81(3) 2.21(3) 2.948(3) 152(3) 2_656
N1 H1B O2 0.87(3) 2.16(3) 3.007(3) 163(3) 1_565
N2 H2A O1 0.81(4) 2.18(4) 2.953(3) 159(3) 1_545
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
_geom_torsion_site_symmetry_4
Br1 C1 C2 O1 -154.7(2) .
Br1 C1 C2 N1 26.7(3) .
Br2 C1 C2 O1 -33.0(3) .
Br2 C1 C2 N1 148.4(2) .
Br3 C1 C2 O1 87.3(3) .
Br3 C1 C2 N1 -91.3(2) .
Br4 C3 C4 O2 -28.8(3) .
Br4 C3 C4 N2 154.8(2) .
Br5 C3 C4 O2 -150.5(2) .
Br5 C3 C4 N2 33.1(3) .
Br6 C3 C4 O2 89.4(3) .
Br6 C3 C4 N2 -87.0(2) .
N3 C5 C6 C7 178.8(3) 3_756
N3 C5 C7 C6 -178.7(3) 3_756
C6 C5 C7 C6 -0.4(5) 3_756
C7 C5 C6 C7 0.4(5) 3_756
C8 N3 C5 C6 35.6(4) .
C8 N3 C5 C7 -146.1(3) .
C9 N3 C5 C6 170.4(3) .
C9 N3 C5 C7 -11.3(4) .
