#------------------------------------------------------------------------------
#$Date: 2025-08-19 21:17:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301807 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/35/2243548.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243548
loop_
_publ_author_name
'Behrman, Edward J.'
'Hansen, Alexandar L.'
'Yuan, Chunhua'
'Parkin, Sean'
_publ_section_title
;
 4,15-Dimethyl-7,12-diazoniatricyclo[10.4.0.0^2,7^]hexadeca-1(12),2,4,6,13,15-hexaene
 dibromide monohydrate
;
_journal_coeditor_code           EX2036
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1467
_journal_page_last               1471
_journal_paper_doi               10.1107/S2056989020011147
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C16 H20 N2 2+, 2(Br -), H2 O'
_chemical_formula_moiety         'C16 H20 N2 2+, 2(Br -), H2 O'
_chemical_formula_sum            'C16 H22 Br2 N2 O'
_chemical_formula_weight         418.17
_chemical_name_systematic
'4,15-Dimethyl-7,12-diazoniatricyclo[10.4.0.0^2,7^]hexadeca-1(12),2,4,6,13,15-hexaene dibromide monohydrate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 101.1620(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6402(2)
_cell_length_b                   13.7578(3)
_cell_length_c                   16.7691(3)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.76
_cell_volume                     1729.30(7)
_computing_cell_refinement
;
APEX3 (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
APEX3 (Bruker, 2016)
;
_computing_molecular_graphics
;
XP in SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELX (Sheldrick, 2008), CIFFIX (Parkin, 2013),
and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 7.41
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26025
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_min         2.476
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    4.688
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_description       'irregular shard'
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.381
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3959
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0197
_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)+(0.0121P)²+1.4994P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0412
_refine_ls_wR_factor_ref         0.0431
_reflns_number_gt                3527
_reflns_number_total             3959
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ex2036sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2243548
_cod_database_fobs_code          2243548
_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   0.521
_shelx_estimated_absorpt_t_max   0.735
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.38758(2) 0.69802(2) 0.11426(2) 0.01809(5) Uani d 1 . .
Br Br2 0.09621(2) 0.58825(2) 0.34885(2) 0.01872(5) Uani d 1 . .
N N1 0.54040(19) 0.38619(10) 0.23392(9) 0.0157(3) Uani d 1 . .
C C1 0.5310(2) 0.34004(13) 0.16231(11) 0.0193(4) Uani d 1 . .
H H1 0.470042 0.279632 0.153665 0.023 Uiso calc 1 . .
C C2 0.6074(2) 0.37819(13) 0.10161(11) 0.0190(4) Uani d 1 . .
H H2 0.598713 0.344145 0.051717 0.023 Uiso calc 1 . .
C C3 0.6973(2) 0.46646(13) 0.11280(10) 0.0164(3) Uani d 1 . .
C C4 0.7082(2) 0.51161(13) 0.18795(10) 0.0159(3) Uani d 1 . .
H H4 0.771186 0.571265 0.198231 0.019 Uiso calc 1 . .
C C5 0.6300(2) 0.47175(12) 0.24753(10) 0.0140(3) Uani d 1 . .
C C6 0.4467(2) 0.34092(13) 0.29478(11) 0.0188(4) Uani d 1 . .
H H6A 0.337285 0.307919 0.266189 0.023 Uiso calc 1 . .
H H6B 0.410854 0.392247 0.329762 0.023 Uiso calc 1 . .
C C7 0.5666(2) 0.26732(13) 0.34768(12) 0.0215(4) Uani d 1 . .
H H7B 0.489315 0.219545 0.368381 0.026 Uiso calc 1 . .
H H7A 0.635324 0.231572 0.312750 0.026 Uiso calc 1 . .
C C8 0.7795(3) 0.51217(14) 0.04805(11) 0.0232(4) Uani d 1 . .
H H8A 0.750594 0.473388 -0.001783 0.035 Uiso calc 1 . .
H H8B 0.909326 0.514930 0.066178 0.035 Uiso calc 1 . .
H H8C 0.732611 0.578163 0.037298 0.035 Uiso calc 1 . .
N N1' 0.72247(18) 0.48640(10) 0.39609(8) 0.0136(3) Uani d 1 . .
C C1' 0.7337(2) 0.53707(13) 0.46545(10) 0.0172(4) Uani d 1 . .
H H1' 0.792782 0.508916 0.515149 0.021 Uiso calc 1 . .
C C2' 0.6619(2) 0.62861(13) 0.46625(10) 0.0170(3) Uani d 1 . .
H H2' 0.673762 0.663389 0.515955 0.020 Uiso calc 1 . .
C C3' 0.5719(2) 0.67031(13) 0.39448(11) 0.0161(3) Uani d 1 . .
C C4' 0.5608(2) 0.61627(12) 0.32318(10) 0.0154(3) Uani d 1 . .
H H4' 0.500590 0.642672 0.272967 0.018 Uiso calc 1 . .
C C5' 0.6360(2) 0.52515(12) 0.32479(10) 0.0135(3) Uani d 1 . .
C C6' 0.8162(2) 0.39082(12) 0.40077(11) 0.0169(4) Uani d 1 . .
H H6A' 0.925433 0.393784 0.443492 0.020 Uiso calc 1 . .
H H6B' 0.852567 0.377516 0.348290 0.020 Uiso calc 1 . .
C C7' 0.6976(2) 0.30844(13) 0.41992(11) 0.0198(4) Uani d 1 . .
H H7A' 0.629120 0.332138 0.460449 0.024 Uiso calc 1 . .
H H7B' 0.775237 0.254877 0.445511 0.024 Uiso calc 1 . .
C C8' 0.4859(2) 0.76805(13) 0.39343(12) 0.0210(4) Uani d 1 . .
H H8A' 0.500384 0.803271 0.344334 0.031 Uiso calc 1 . .
H H8B' 0.542276 0.804908 0.441597 0.031 Uiso calc 1 . .
H H8C' 0.358509 0.760037 0.393689 0.031 Uiso calc 1 . .
O O1W 0.1964(2) 0.49717(11) 0.17678(9) 0.0297(3) Uani d 1 . .
H H1W 0.240(3) 0.5445(16) 0.1598(16) 0.044 Uiso d 1 . .
H H2W 0.168(3) 0.5155(19) 0.2183(13) 0.044 Uiso d 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C5 . . 119.74(15) ?
C1 N1 C6 . . 117.59(15) ?
C5 N1 C6 . . 122.66(14) ?
N1 C1 C2 . . 121.59(17) ?
N1 C1 H1 . . 119.2 ?
C2 C1 H1 . . 119.2 ?
C1 C2 C3 . . 120.29(16) ?
C1 C2 H2 . . 119.9 ?
C3 C2 H2 . . 119.9 ?
C2 C3 C4 . . 116.94(16) ?
C2 C3 C8 . . 122.41(16) ?
C4 C3 C8 . . 120.65(16) ?
C5 C4 C3 . . 121.45(16) ?
C5 C4 H4 . . 119.3 ?
C3 C4 H4 . . 119.3 ?
N1 C5 C4 . . 119.97(15) ?
N1 C5 C5' . . 120.37(15) ?
C4 C5 C5' . . 119.58(15) ?
N1 C6 C7 . . 111.16(14) ?
N1 C6 H6A . . 109.4 ?
C7 C6 H6A . . 109.4 ?
N1 C6 H6B . . 109.4 ?
C7 C6 H6B . . 109.4 ?
H6A C6 H6B . . 108.0 ?
C7' C7 C6 . . 116.31(15) ?
C7' C7 H7B . . 108.2 ?
C6 C7 H7B . . 108.2 ?
C7' C7 H7A . . 108.2 ?
C6 C7 H7A . . 108.2 ?
H7B C7 H7A . . 107.4 ?
C3 C8 H8A . . 109.5 ?
C3 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C3 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C1' N1' C5' . . 119.79(15) ?
C1' N1' C6' . . 117.50(14) ?
C5' N1' C6' . . 122.62(14) ?
N1' C1' C2' . . 121.64(16) ?
N1' C1' H1' . . 119.2 ?
C2' C1' H1' . . 119.2 ?
C1' C2' C3' . . 120.09(16) ?
C1' C2' H2' . . 120.0 ?
C3' C2' H2' . . 120.0 ?
C2' C3' C4' . . 117.37(16) ?
C2' C3' C8' . . 121.61(16) ?
C4' C3' C8' . . 121.00(16) ?
C5' C4' C3' . . 120.79(16) ?
C5' C4' H4' . . 119.6 ?
C3' C4' H4' . . 119.6 ?
N1' C5' C4' . . 120.31(15) ?
N1' C5' C5 . . 120.15(15) ?
C4' C5' C5 . . 119.46(15) ?
N1' C6' C7' . . 111.60(14) ?
N1' C6' H6A' . . 109.3 ?
C7' C6' H6A' . . 109.3 ?
N1' C6' H6B' . . 109.3 ?
C7' C6' H6B' . . 109.3 ?
H6A' C6' H6B' . . 108.0 ?
C6' C7' C7 . . 115.78(15) ?
C6' C7' H7A' . . 108.3 ?
C7 C7' H7A' . . 108.3 ?
C6' C7' H7B' . . 108.3 ?
C7 C7' H7B' . . 108.3 ?
H7A' C7' H7B' . . 107.4 ?
C3' C8' H8A' . . 109.5 ?
C3' C8' H8B' . . 109.5 ?
H8A' C8' H8B' . . 109.5 ?
C3' C8' H8C' . . 109.5 ?
H8A' C8' H8C' . . 109.5 ?
H8B' C8' H8C' . . 109.5 ?
H1W O1W H2W . . 104(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . 1.348(2) ?
N1 C5 . 1.359(2) ?
N1 C6 . 1.491(2) ?
C1 C2 . 1.372(3) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.390(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.393(2) ?
C3 C8 . 1.494(2) ?
C4 C5 . 1.374(2) ?
C4 H4 . 0.9500 ?
C5 C5' . 1.482(2) ?
C6 C7 . 1.528(3) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C7' . 1.523(3) ?
C7 H7B . 0.9900 ?
C7 H7A . 0.9900 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
N1' C1' . 1.344(2) ?
N1' C5' . 1.358(2) ?
N1' C6' . 1.492(2) ?
C1' C2' . 1.375(2) ?
C1' H1' . 0.9500 ?
C2' C3' . 1.389(2) ?
C2' H2' . 0.9500 ?
C3' C4' . 1.396(2) ?
C3' C8' . 1.495(2) ?
C4' C5' . 1.377(2) ?
C4' H4' . 0.9500 ?
C6' C7' . 1.523(2) ?
C6' H6A' . 0.9900 ?
C6' H6B' . 0.9900 ?
C7' H7A' . 0.9900 ?
C7' H7B' . 0.9900 ?
C8' H8A' . 0.9800 ?
C8' H8B' . 0.9800 ?
C8' H8C' . 0.9800 ?
O1W H1W . 0.809(19) ?
O1W H2W . 0.807(19) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C1 H1 Br2 2_545 0.95 2.68 3.5929(18) 161.3 yes
C2 H2 Br1 3_665 0.95 2.86 3.7762(18) 161.1 yes
C7 H7B Br1 2_545 0.99 2.96 3.7700(19) 139.2 yes
C1' H1' Br2 3_666 0.95 2.64 3.5765(17) 169.6 yes
C2' H2' Br1 4_676 0.95 2.82 3.6285(17) 143.0 yes
C4' H4' Br1 . 0.95 2.74 3.6735(17) 166.9 yes
C7' H7B' Br1 2_645 0.99 3.04 3.6581(18) 121.5 yes
O1W H1W Br1 . 0.809(19) 2.577(19) 3.3856(15) 177(3) yes
O1W H2W Br2 . 0.807(19) 2.563(19) 3.3670(15) 175(3) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C1 C2 . . . . -1.2(3) ?
C6 N1 C1 C2 . . . . 177.51(16) ?
N1 C1 C2 C3 . . . . 0.0(3) ?
C1 C2 C3 C4 . . . . 1.3(2) ?
C1 C2 C3 C8 . . . . -178.70(17) ?
C2 C3 C4 C5 . . . . -1.5(2) ?
C8 C3 C4 C5 . . . . 178.50(16) ?
C1 N1 C5 C4 . . . . 1.0(2) ?
C6 N1 C5 C4 . . . . -177.65(15) ?
C1 N1 C5 C5' . . . . 177.79(15) ?
C6 N1 C5 C5' . . . . -0.8(2) ?
C3 C4 C5 N1 . . . . 0.4(3) ?
C3 C4 C5 C5' . . . . -176.45(15) ?
C1 N1 C6 C7 . . . . 87.25(19) ?
C5 N1 C6 C7 . . . . -94.09(19) ?
N1 C6 C7 C7' . . . . 83.16(19) ?
C5' N1' C1' C2' . . . . -1.0(2) ?
C6' N1' C1' C2' . . . . 175.61(15) ?
N1' C1' C2' C3' . . . . 1.3(3) ?
C1' C2' C3' C4' . . . . -0.8(2) ?
C1' C2' C3' C8' . . . . 177.56(16) ?
C2' C3' C4' C5' . . . . 0.2(2) ?
C8' C3' C4' C5' . . . . -178.18(16) ?
C1' N1' C5' C4' . . . . 0.4(2) ?
C6' N1' C5' C4' . . . . -176.07(15) ?
C1' N1' C5' C5 . . . . 177.22(15) ?
C6' N1' C5' C5 . . . . 0.8(2) ?
C3' C4' C5' N1' . . . . 0.0(2) ?
C3' C4' C5' C5 . . . . -176.85(15) ?
N1 C5 C5' N1' . . . . 66.1(2) ?
C4 C5 C5' N1' . . . . -117.12(18) ?
N1 C5 C5' C4' . . . . -117.09(18) ?
C4 C5 C5' C4' . . . . 59.7(2) ?
C1' N1' C6' C7' . . . . 88.23(18) ?
C5' N1' C6' C7' . . . . -95.23(19) ?
N1' C6' C7' C7 . . . . 82.48(19) ?
C6 C7 C7' C6' . . . . -52.2(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168326805
