#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/24/1542471.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_1542471
loop_
_publ_author_name
'Abdelhamida, Antar A.'
'Mohamed, Shaaban K.'
'Simpson, Jim'
_publ_section_title
;
 3,3'-[(Cyclohexane-1,4-diyl)bis(azanediyl)]bis(cyclohex-2-en-1-one)
;
_journal_coeditor_code           SU4002
_journal_issue                   1
_journal_name_full               IUCrData
_journal_page_first              x152175
_journal_paper_doi               10.1107/S2414314615021756
_journal_volume                  1
_journal_year                    2016
_chemical_formula_moiety         'C18 H26 N2 O2'
_chemical_formula_sum            'C18 H26 N2 O2'
_chemical_formula_weight         302.41
_chemical_name_systematic
;
3,3'-[(Cyclohexane-1,4-diyl)bis(azanediyl)]bis(cyclohex-2-en-1-one)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                106.557(3)
_cell_angle_beta                 97.687(2)
_cell_angle_gamma                96.630(2)
_cell_formula_units_Z            2
_cell_length_a                   8.1839(2)
_cell_length_b                   9.1461(3)
_cell_length_c                   11.7669(4)
_cell_measurement_reflns_used    9205
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.0580
_cell_measurement_theta_min      3.9650
_cell_volume                     825.65(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent (2013)
;
_computing_data_collection
;
CrysAlisPro, Agilent (2013)
;
_computing_data_reduction
;
CrysAlisPro, Agilent (2013)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL2014/7 (Sheldrick, 2015b), enCIFer (Allen et al.,
2004),
PLATON (Spek, 2009),  publCIF (Westrip 2010), WINGX (Farrugia
2012)
;
_computing_structure_refinement
;
SHELXL2014/7 (Sheldrick, 2015b) and TITAN2000 (Hunter &
Simpson,
1999)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1725
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12078
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.074
_diffrn_reflns_theta_min         3.981
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Agilent, 2013)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3272
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0523P)²+0.2392P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1033
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3002
_reflns_number_total             3272
_reflns_threshold_expression     'I > 2σ(I)'
_publcif_datablock.id            {5c06c443-d613-43a7-9497-c86907c2dfae}
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_cod_data_source_file            su4002sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 1542471.cif.'
_cod_database_code               1542471
_cod_database_fobs_code          1542471
#BEGIN Tags that were not found in dictionaries:
_shelx_shelxl_version_number     2014/7
_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   0.728
_shelx_estimated_absorpt_t_max   0.957
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
O11' O 0.17860(10) 0.83044(9) 0.13490(7) 0.0202(2) Uani 1 1 d . .
C11' C 0.32063(14) 0.79299(12) 0.14231(9) 0.0170(2) Uani 1 1 d . .
C12' C 0.38277(14) 0.72110(13) 0.22838(10) 0.0177(2) Uani 1 1 d . .
H12' H 0.3140 0.7018 0.2832 0.021 Uiso 1 1 calc R U
C13' C 0.53902(14) 0.67872(12) 0.23469(9) 0.0162(2) Uani 1 1 d . .
N11 N 0.59935(12) 0.60257(11) 0.30855(9) 0.0184(2) Uani 1 1 d . .
H11N H 0.708(2) 0.5950(16) 0.3150(13) 0.022 Uiso 1 1 d . U
C11 C 0.50682(13) 0.54283(13) 0.38859(10) 0.0165(2) Uani 1 1 d . .
H11 H 0.3873 0.5081 0.3483 0.020 Uiso 1 1 calc R U
C12 C 0.57883(15) 0.40283(13) 0.40741(10) 0.0187(2) Uani 1 1 d . .
H12A H 0.6989 0.4342 0.4432 0.022 Uiso 1 1 calc R U
H12B H 0.5690 0.3230 0.3286 0.022 Uiso 1 1 calc R U
C16 C 0.51340(15) 0.66504(13) 0.50964(10) 0.0181(2) Uani 1 1 d . .
H161 H 0.6304(17) 0.7022(15) 0.5469(12) 0.016(3) Uiso 1 1 d . .
H162 H 0.4644(18) 0.7539(16) 0.4973(13) 0.022(3) Uiso 1 1 d . .
C14' C 0.65503(14) 0.71158(13) 0.15190(10) 0.0180(2) Uani 1 1 d . .
H14A H 0.6440 0.6187 0.0813 0.022 Uiso 1 1 calc R U
H14B H 0.7719 0.7339 0.1950 0.022 Uiso 1 1 calc R U
C15' C 0.61656(15) 0.84812(14) 0.10889(10) 0.0208(3) Uani 1 1 d . .
H15A H 0.6848 0.8584 0.0474 0.025 Uiso 1 1 calc R U
H15B H 0.6452 0.9446 0.1774 0.025 Uiso 1 1 calc R U
C16' C 0.43164(15) 0.82319(14) 0.05536(11) 0.0224(3) Uani 1 1 d . .
H16C H 0.4059 0.9159 0.0335 0.027 Uiso 1 1 calc R U
H16D H 0.4072 0.7342 -0.0192 0.027 Uiso 1 1 calc R U
O21' O 0.94724(10) 0.59292(9) 0.34302(7) 0.01825(19) Uani 1 1 d . .
C21' C 0.98783(13) 0.47129(12) 0.28124(9) 0.0147(2) Uani 1 1 d . .
C22' C 1.01924(13) 0.34896(12) 0.32908(9) 0.0154(2) Uani 1 1 d . .
H22' H 1.0180 0.3630 0.4121 0.018 Uiso 1 1 calc R U
C23' C 1.05146(13) 0.21036(12) 0.25822(9) 0.0148(2) Uani 1 1 d . .
N21 N 1.07308(12) 0.08956(11) 0.29800(8) 0.0164(2) Uani 1 1 d . .
H21N H 1.0982(17) 0.0065(17) 0.2477(13) 0.020 Uiso 1 1 d . U
C21 C 1.05449(14) 0.08363(12) 0.41861(9) 0.0149(2) Uani 1 1 d . .
H21 H 1.1054 0.1860 0.4782 0.018 Uiso 1 1 calc R U
C22 C 1.14853(14) -0.03970(12) 0.44659(9) 0.0162(2) Uani 1 1 d . .
H22A H 1.2683 -0.0137 0.4433 0.019 Uiso 1 1 calc R U
H22B H 1.1038 -0.1409 0.3854 0.019 Uiso 1 1 calc R U
C26 C 0.86983(14) 0.05044(13) 0.42843(10) 0.0165(2) Uani 1 1 d . .
H261 H 0.8108(17) 0.1327(16) 0.4127(13) 0.020 Uiso 1 1 d . U
H262 H 0.8183(17) -0.0501(16) 0.3656(13) 0.020 Uiso 1 1 d . U
C24' C 1.06061(15) 0.18458(12) 0.12708(9) 0.0173(2) Uani 1 1 d . .
H24A H 0.9503 0.1330 0.0778 0.021 Uiso 1 1 calc R U
H24B H 1.1429 0.1152 0.1038 0.021 Uiso 1 1 calc R U
C25' C 1.11107(14) 0.33592(13) 0.10069(9) 0.0175(2) Uani 1 1 d . .
H25A H 1.2290 0.3788 0.1382 0.021 Uiso 1 1 calc R U
H25B H 1.1011 0.3163 0.0127 0.021 Uiso 1 1 calc R U
C26' C 0.99899(14) 0.45218(12) 0.15038(10) 0.0174(2) Uani 1 1 d . .
H26A H 1.0428 0.5537 0.1425 0.021 Uiso 1 1 calc R U
H26B H 0.8854 0.4178 0.1015 0.021 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
O11' C11' C12' 122.81(10) . .
O11' C11' C16' 118.83(10) . .
C12' C11' C16' 118.36(10) . .
C13' C12' C11' 122.23(10) . .
C13' C12' H12' 118.9 . .
C11' C12' H12' 118.9 . .
N11 C13' C12' 124.62(10) . .
N11 C13' C14' 114.55(10) . .
C12' C13' C14' 120.79(10) . .
C13' N11 C11 125.64(10) . .
C13' N11 H11N 117.4(9) . .
C11 N11 H11N 116.7(9) . .
N11 C11 C12 108.57(9) . .
N11 C11 C16 112.30(9) . .
C12 C11 C16 110.44(9) . .
N11 C11 H11 108.5 . .
C12 C11 H11 108.5 . .
C16 C11 H11 108.5 . .
C11 C12 C16 110.98(9) . 2_666
C11 C12 H12A 109.4 . .
C16 C12 H12A 109.4 2_666 .
C11 C12 H12B 109.4 . .
C16 C12 H12B 109.4 2_666 .
H12A C12 H12B 108.0 . .
C11 C16 C12 110.90(9) . 2_666
C11 C16 H161 108.2(8) . .
C12 C16 H161 109.8(8) 2_666 .
C11 C16 H162 110.2(8) . .
C12 C16 H162 110.0(8) 2_666 .
H161 C16 H162 107.6(11) . .
C13' C14' C15' 111.81(9) . .
C13' C14' H14A 109.3 . .
C15' C14' H14A 109.3 . .
C13' C14' H14B 109.3 . .
C15' C14' H14B 109.3 . .
H14A C14' H14B 107.9 . .
C14' C15' C16' 109.70(9) . .
C14' C15' H15A 109.7 . .
C16' C15' H15A 109.7 . .
C14' C15' H15B 109.7 . .
C16' C15' H15B 109.7 . .
H15A C15' H15B 108.2 . .
C11' C16' C15' 112.08(9) . .
C11' C16' H16C 109.2 . .
C15' C16' H16C 109.2 . .
C11' C16' H16D 109.2 . .
C15' C16' H16D 109.2 . .
H16C C16' H16D 107.9 . .
O21' C21' C22' 122.03(10) . .
O21' C21' C26' 118.86(9) . .
C22' C21' C26' 119.09(9) . .
C23' C22' C21' 121.82(10) . .
C23' C22' H22' 119.1 . .
C21' C22' H22' 119.1 . .
N21 C23' C22' 123.77(10) . .
N21 C23' C24' 115.16(9) . .
C22' C23' C24' 121.05(10) . .
C23' N21 C21 124.53(9) . .
C23' N21 H21N 118.1(9) . .
C21 N21 H21N 117.4(9) . .
N21 C21 C22 108.82(9) . .
N21 C21 C26 111.15(9) . .
C22 C21 C26 110.89(9) . .
N21 C21 H21 108.6 . .
C22 C21 H21 108.6 . .
C26 C21 H21 108.6 . .
C21 C22 C26 110.27(9) . 2_756
C21 C22 H22A 109.6 . .
C26 C22 H22A 109.6 2_756 .
C21 C22 H22B 109.6 . .
C26 C22 H22B 109.6 2_756 .
H22A C22 H22B 108.1 . .
C22 C26 C21 110.87(9) 2_756 .
C22 C26 H261 109.2(8) 2_756 .
C21 C26 H261 110.3(8) . .
C22 C26 H262 109.8(8) 2_756 .
C21 C26 H262 108.1(8) . .
H261 C26 H262 108.5(11) . .
C23' C24' C25' 111.93(9) . .
C23' C24' H24A 109.2 . .
C25' C24' H24A 109.2 . .
C23' C24' H24B 109.2 . .
C25' C24' H24B 109.2 . .
H24A C24' H24B 107.9 . .
C26' C25' C24' 110.10(9) . .
C26' C25' H25A 109.6 . .
C24' C25' H25A 109.6 . .
C26' C25' H25B 109.6 . .
C24' C25' H25B 109.6 . .
H25A C25' H25B 108.2 . .
C21' C26' C25' 112.89(9) . .
C21' C26' H26A 109.0 . .
C25' C26' H26A 109.0 . .
C21' C26' H26B 109.0 . .
C25' C26' H26B 109.0 . .
H26A C26' H26B 107.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O11' C11' 1.2481(14) .
C11' C12' 1.4267(15) .
C11' C16' 1.5167(15) .
C12' C13' 1.3771(16) .
C12' H12' 0.9500 .
C13' N11 1.3394(15) .
C13' C14' 1.5131(15) .
N11 C11 1.4654(13) .
N11 H11N 0.896(16) .
C11 C12 1.5287(15) .
C11 C16 1.5295(16) .
C11 H11 1.0000 .
C12 C16 1.5303(14) 2_666
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C16 C12 1.5303(14) 2_666
C16 H161 0.976(14) .
C16 H162 0.984(15) .
C14' C15' 1.5241(15) .
C14' H14A 0.9900 .
C14' H14B 0.9900 .
C15' C16' 1.5240(17) .
C15' H15A 0.9900 .
C15' H15B 0.9900 .
C16' H16C 0.9900 .
C16' H16D 0.9900 .
O21' C21' 1.2512(13) .
C21' C22' 1.4217(15) .
C21' C26' 1.5159(14) .
C22' C23' 1.3803(15) .
C22' H22' 0.9500 .
C23' N21 1.3375(14) .
C23' C24' 1.5067(14) .
N21 C21 1.4629(13) .
N21 H21N 0.884(15) .
C21 C22 1.5223(15) .
C21 C26 1.5330(15) .
C21 H21 1.0000 .
C22 C26 1.5274(14) 2_756
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C26 C22 1.5274(14) 2_756
C26 H261 0.987(15) .
C26 H262 1.005(14) .
C24' C25' 1.5264(15) .
C24' H24A 0.9900 .
C24' H24B 0.9900 .
C25' C26' 1.5259(15) .
C25' H25A 0.9900 .
C25' H25B 0.9900 .
C26' H26A 0.9900 .
C26' H26B 0.9900 .
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
N11 H11N O21' 0.896(16) 1.944(16) 2.8369(13) 174.8(14) .
N21 H21N O11' 0.884(15) 2.012(15) 2.8930(13) 174.1(13) 1_645
C21 H21 O21' 1.00 2.59 3.4511(13) 144 2_766
C22 H22B O21' 0.99 2.50 3.3675(14) 147 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
O11' C11' C12' C13' 179.23(10) .
C16' C11' C12' C13' -0.02(16) .
C11' C12' C13' N11 -175.70(10) .
C11' C12' C13' C14' 1.92(17) .
C12' C13' N11 C11 4.30(18) .
C14' C13' N11 C11 -173.45(10) .
C13' N11 C11 C12 152.07(11) .
C13' N11 C11 C16 -85.51(13) .
N11 C11 C12 C16 -179.88(9) 2_666
C16 C11 C12 C16 56.59(13) 2_666
N11 C11 C16 C12 -177.89(9) 2_666
C12 C11 C16 C12 -56.54(13) 2_666
N11 C13' C14' C15' -156.94(10) .
C12' C13' C14' C15' 25.22(14) .
C13' C14' C15' C16' -52.41(13) .
O11' C11' C16' C15' 151.78(10) .
C12' C11' C16' C15' -28.93(14) .
C14' C15' C16' C11' 54.51(13) .
O21' C21' C22' C23' 174.96(10) .
C26' C21' C22' C23' -3.27(16) .
C21' C22' C23' N21 -176.41(10) .
C21' C22' C23' C24' 2.13(16) .
C22' C23' N21 C21 4.36(17) .
C24' C23' N21 C21 -174.25(9) .
C23' N21 C21 C22 -159.15(10) .
C23' N21 C21 C26 78.46(13) .
N21 C21 C22 C26 -179.35(8) 2_756
C26 C21 C22 C26 -56.80(12) 2_756
N21 C21 C26 C22 178.33(9) 2_756
C22 C21 C26 C22 57.15(12) 2_756
N21 C23' C24' C25' -155.02(10) .
C22' C23' C24' C25' 26.32(14) .
C23' C24' C25' C26' -51.78(12) .
O21' C21' C26' C25' 157.43(10) .
C22' C21' C26' C25' -24.28(14) .
C24' C25' C26' C21' 51.07(12) .
loop_
_publcif_info_cif.paper_type
EX
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{5c06c443-d613-43a7-9497-c86907c2dfae} y y y
{177ecfbe-1c31-444f-a64a-41d952285550} ? ? ?
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{5c06c443-d613-43a7-9497-c86907c2dfae} '_geom_hbond_atom_site_label_D'
{177ecfbe-1c31-444f-a64a-41d952285550} '_publcif_info_datablock.publ_exptl'
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139048059
