#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/35/2233528.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_2233528
loop_
_publ_author_name
'Abdul Rahim, Munirah Sufiyah'
'Khaledi, Hamid'
'Alias, Yatimah'
'Welz-Biermann, Urs'
_publ_section_title
;
 N,N'-[1,4-Phenylenebis(methylene)]bis(N,N-diethylethanaminium)
 dibromide
;
_journal_coeditor_code           IS5042
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o369
_journal_paper_doi               10.1107/S1600536812000141
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C20 H38 N2 2+, 2Br -'
_chemical_formula_moiety         'C20 H38 N2 2+, 2(Br -)'
_chemical_formula_sum            'C20 H38 Br2 N2'
_chemical_formula_weight         466.34
_chemical_name_systematic
;
N,N'-[1,4-Phenylenebis(methylene)]bis(N,N-
diethylethanaminium) dibromide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.6340(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.2713(5)
_cell_length_b                   14.1440(9)
_cell_length_c                   9.0762(6)
_cell_measurement_reflns_used    8155
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.68
_cell_volume                     1052.41(12)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10066
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.68
_exptl_absorpt_coefficient_mu    3.856
_exptl_absorpt_correction_T_max  0.3455
_exptl_absorpt_correction_T_min  0.2438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.232
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2304
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0204
_refine_ls_R_factor_gt           0.0174
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0190P)²+0.5002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0423
_refine_ls_wR_factor_ref         0.0433
_reflns_number_gt                2093
_reflns_number_total             2304
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            is5042.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2233528
_cod_database_fobs_code          2233528
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
N N1 0.82236(14) 0.33100(8) 0.70235(13) 0.0099(2) Uani d . 1 1
C C1 0.72184(18) 0.46030(11) 0.87038(16) 0.0176(3) Uani d . 1 1
H H1A 0.8299 0.4897 0.8894 0.026 Uiso calc R 1 1
H H1B 0.6651 0.4681 0.9578 0.026 Uiso calc R 1 1
H H1C 0.6585 0.4906 0.7843 0.026 Uiso calc R 1 1
C C2 0.74049(18) 0.35590(10) 0.83906(15) 0.0138(3) Uani d . 1 1
H H2A 0.6308 0.3267 0.8271 0.017 Uiso calc R 1 1
H H2B 0.8045 0.3266 0.9273 0.017 Uiso calc R 1 1
C C3 1.10397(18) 0.38839(11) 0.80909(16) 0.0156(3) Uani d . 1 1
H H3A 1.0615 0.3870 0.9049 0.023 Uiso calc R 1 1
H H3B 1.1769 0.4428 0.8062 0.023 Uiso calc R 1 1
H H3C 1.1644 0.3300 0.7967 0.023 Uiso calc R 1 1
C C4 0.96263(16) 0.39682(10) 0.68396(15) 0.0120(3) Uani d . 1 1
H H4A 0.9223 0.4628 0.6796 0.014 Uiso calc R 1 1
H H4B 1.0028 0.3828 0.5883 0.014 Uiso calc R 1 1
C C5 0.97084(18) 0.18930(11) 0.60528(17) 0.0166(3) Uani d . 1 1
H H5A 0.8954 0.1845 0.5127 0.025 Uiso calc R 1 1
H H5B 1.0132 0.1264 0.6346 0.025 Uiso calc R 1 1
H H5C 1.0616 0.2311 0.5900 0.025 Uiso calc R 1 1
C C6 0.88154(17) 0.22941(10) 0.72681(16) 0.0131(3) Uani d . 1 1
H H6A 0.9550 0.2263 0.8221 0.016 Uiso calc R 1 1
H H6B 0.7862 0.1887 0.7364 0.016 Uiso calc R 1 1
C C7 0.69822(17) 0.33096(10) 0.56112(15) 0.0113(3) Uani d . 1 1
H H7A 0.7577 0.3197 0.4750 0.014 Uiso calc R 1 1
H H7B 0.6231 0.2770 0.5668 0.014 Uiso calc R 1 1
C C8 0.59739(16) 0.41916(10) 0.53110(15) 0.0110(3) Uani d . 1 1
C C9 0.43874(17) 0.42236(10) 0.56832(15) 0.0124(3) Uani d . 1 1
H H9 0.3958 0.3692 0.6139 0.015 Uiso calc R 1 1
C C10 0.65646(17) 0.49722(10) 0.46095(15) 0.0126(3) Uani d . 1 1
H H10 0.7630 0.4954 0.4329 0.015 Uiso calc R 1 1
Br Br1 0.937757(16) 0.344754(10) 0.237945(15) 0.01420(6) Uani d . 1 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'
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'
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
C4 N1 C6 . 111.08(10)
C4 N1 C2 . 112.07(11)
C6 N1 C2 . 105.47(10)
C4 N1 C7 . 110.25(10)
C6 N1 C7 . 106.74(10)
C2 N1 C7 . 111.01(10)
C2 C1 H1A . 109.5
C2 C1 H1B . 109.5
H1A C1 H1B . 109.5
C2 C1 H1C . 109.5
H1A C1 H1C . 109.5
H1B C1 H1C . 109.5
C1 C2 N1 . 116.30(12)
C1 C2 H2A . 108.2
N1 C2 H2A . 108.2
C1 C2 H2B . 108.2
N1 C2 H2B . 108.2
H2A C2 H2B . 107.4
C4 C3 H3A . 109.5
C4 C3 H3B . 109.5
H3A C3 H3B . 109.5
C4 C3 H3C . 109.5
H3A C3 H3C . 109.5
H3B C3 H3C . 109.5
N1 C4 C3 . 113.17(11)
N1 C4 H4A . 108.9
C3 C4 H4A . 108.9
N1 C4 H4B . 108.9
C3 C4 H4B . 108.9
H4A C4 H4B . 107.8
C6 C5 H5A . 109.5
C6 C5 H5B . 109.5
H5A C5 H5B . 109.5
C6 C5 H5C . 109.5
H5A C5 H5C . 109.5
H5B C5 H5C . 109.5
C5 C6 N1 . 115.13(12)
C5 C6 H6A . 108.5
N1 C6 H6A . 108.5
C5 C6 H6B . 108.5
N1 C6 H6B . 108.5
H6A C6 H6B . 107.5
C8 C7 N1 . 116.41(11)
C8 C7 H7A . 108.2
N1 C7 H7A . 108.2
C8 C7 H7B . 108.2
N1 C7 H7B . 108.2
H7A C7 H7B . 107.3
C10 C8 C9 . 118.77(13)
C10 C8 C7 . 121.29(12)
C9 C8 C7 . 119.88(13)
C10 C9 C8 3_666 120.44(13)
C10 C9 H9 3_666 119.8
C8 C9 H9 . 119.8
C9 C10 C8 3_666 120.76(13)
C9 C10 H10 3_666 119.6
C8 C10 H10 . 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C4 . 1.5140(17)
N1 C6 . 1.5246(18)
N1 C2 . 1.5314(17)
N1 C7 . 1.5322(17)
C1 C2 . 1.516(2)
C1 H1A . 0.9800
C1 H1B . 0.9800
C1 H1C . 0.9800
C2 H2A . 0.9900
C2 H2B . 0.9900
C3 C4 . 1.5225(19)
C3 H3A . 0.9800
C3 H3B . 0.9800
C3 H3C . 0.9800
C4 H4A . 0.9900
C4 H4B . 0.9900
C5 C6 . 1.517(2)
C5 H5A . 0.9800
C5 H5B . 0.9800
C5 H5C . 0.9800
C6 H6A . 0.9900
C6 H6B . 0.9900
C7 C8 . 1.5052(19)
C7 H7A . 0.9900
C7 H7B . 0.9900
C8 C10 . 1.395(2)
C8 C9 . 1.3986(19)
C9 C10 3_666 1.389(2)
C9 H9 . 0.9500
C10 C9 3_666 1.389(2)
C10 H10 . 0.9500
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
C7 H7A Br1 . 0.99 2.80 3.7565(14) 163.3
C2 H2B Br1 1_556 0.99 2.90 3.7716(14) 147.5
C6 H6B Br1 4_566 0.99 2.92 3.8318(14) 153.2
C7 H7B Br1 4_566 0.99 2.89 3.7832(14) 150.3
C1 H1C Cg . 0.98 2.74 3.6529(16) 156
loop_
_iucr_refine_instructions_details
;
TITL 1
CELL 0.71073 8.2713 14.1440 9.0762 90.000 97.634 90.000
ZERR 2.00 0.0005 0.0009 0.0006 0.000 0.001 0.000
LATT 1
SYMM -x+1/2, y+1/2, -z+1/2
SFAC C  H  N  Br
UNIT 40  76  4  4
omit 4 9 9
OMIT -2 54
L.S. 24
HTAB C7 Br1
HTAB C2 Br1_$1
HTAB C6 Br1_$2
HTAB C7 Br1_$2
EQIV $2 -1/2+x,1/2-y,1/2+z
EQIV $1 x,y,1+z
ACTA
SIZE 0.51 0.47 0.35
BOND $H
TEMP -173
WGHT    0.019000    0.500200
FVAR       0.21490
N1    3    0.822358    0.330996    0.702352    11.00000    0.01065    0.00844 =
         0.01032    0.00170   -0.00020    0.00028
C1    1    0.721837    0.460299    0.870382    11.00000    0.02187    0.01772 =
         0.01358   -0.00402    0.00345    0.00055
AFIX 137
H1A   2    0.829879    0.489707    0.889369    11.00000   -1.50000
H1B   2    0.665101    0.468112    0.957769    11.00000   -1.50000
H1C   2    0.658466    0.490588    0.784261    11.00000   -1.50000
AFIX   0
C2    1    0.740495    0.355897    0.839060    11.00000    0.01518    0.01637 =
         0.01024   -0.00010    0.00351   -0.00061
AFIX  23
H2A   2    0.630764    0.326684    0.827075    11.00000   -1.20000
H2B   2    0.804506    0.326630    0.927274    11.00000   -1.20000
AFIX   0
C3    1    1.103966    0.388393    0.809095    11.00000    0.01361    0.01598 =
         0.01615    0.00114   -0.00216   -0.00264
AFIX 137
H3A   2    1.061537    0.387033    0.904881    11.00000   -1.50000
H3B   2    1.176931    0.442761    0.806227    11.00000   -1.50000
H3C   2    1.164405    0.329964    0.796723    11.00000   -1.50000
AFIX   0
C4    1    0.962631    0.396816    0.683962    11.00000    0.01258    0.01066 =
         0.01264    0.00081    0.00087   -0.00289
AFIX  23
H4A   2    0.922283    0.462786    0.679647    11.00000   -1.20000
H4B   2    1.002789    0.382778    0.588308    11.00000   -1.20000
AFIX   0
C5    1    0.970844    0.189295    0.605285    11.00000    0.01621    0.01182 =
         0.02125   -0.00115    0.00052    0.00332
AFIX 137
H5A   2    0.895417    0.184475    0.512722    11.00000   -1.50000
H5B   2    1.013186    0.126384    0.634587    11.00000   -1.50000
H5C   2    1.061630    0.231106    0.590028    11.00000   -1.50000
AFIX   0
C6    1    0.881537    0.229412    0.726806    11.00000    0.01368    0.00891 =
         0.01603    0.00338   -0.00071    0.00111
AFIX  23
H6A   2    0.955008    0.226295    0.822131    11.00000   -1.20000
H6B   2    0.786169    0.188678    0.736426    11.00000   -1.20000
AFIX   0
C7    1    0.698220    0.330960    0.561122    11.00000    0.01108    0.01117 =
         0.01078   -0.00081   -0.00201   -0.00067
AFIX  23
H7A   2    0.757716    0.319690    0.475044    11.00000   -1.20000
H7B   2    0.623106    0.276980    0.566803    11.00000   -1.20000
AFIX   0
C8    1    0.597392    0.419158    0.531100    11.00000    0.01220    0.01052 =
         0.00948   -0.00051   -0.00167    0.00088
C9    1    0.438736    0.422362    0.568319    11.00000    0.01318    0.01148 =
         0.01241    0.00286    0.00105   -0.00131
AFIX  43
H9    2    0.395801    0.369172    0.613925    11.00000   -1.20000
AFIX   0
C10   1    0.656462    0.497222    0.460948    11.00000    0.01059    0.01490 =
         0.01211    0.00062    0.00122    0.00009
AFIX  43
H10   2    0.763044    0.495356    0.432870    11.00000   -1.20000
AFIX   0
BR1   4    0.937757    0.344754    0.237945    11.00000    0.01526    0.01314 =
         0.01435    0.00042    0.00246    0.00247
HKLF 4 1 1 0 0 0 1 0 0 0 1
REM  safwan3055_0m in P2(1)/n
REM R1 =  0.0174 for   2093 Fo > 4sig(Fo)  and  0.0204 for all   2304 data
REM    112 parameters refined using      0 restraints
END
WGHT      0.0190      0.5003
REM Highest difference peak  0.430,  deepest hole -0.232,  1-sigma level  0.054
Q1    1   0.5231  0.4227  0.5617  11.00000  0.05    0.43
Q2    1   0.9424  0.3401  0.3317  11.00000  0.05    0.35
Q3    1   0.6185  0.4573  0.4906  11.00000  0.05    0.34
Q4    1   1.0474  0.3464  0.2393  11.00000  0.05    0.34
Q5    1   0.8290  0.3470  0.2467  11.00000  0.05    0.33
;
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 24833607
