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#$Date: 2024-05-18 04:51:48 +0300 (Sat, 18 May 2024) $
#$Revision: 291951 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/31/2023131.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_2023131
loop_
_publ_author_name
'Sadikhova, Nurlana D.'
'Akkurt, Mehmet'
'Ismayilov, Valeh M.'
'Yusubov, Niftali N.'
'Hasanov, Khudayar I.'
'Bhattarai, Ajaya'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 3,3′-[ethane-1,2-diylbis(oxy)]bis(5,5-dimethylcyclohex-2-en-1-one)
 including an unknown solvate
;
_journal_coeditor_code           NX2010
_journal_issue                   6
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989024004286
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C18 H26 O4'
_chemical_formula_moiety         'C18 H26 O4'
_chemical_formula_sum            'C18 H26 O4'
_chemical_formula_weight         306.39
_chemical_name_systematic
;
3,3'-[Ethane-1,2-diylbis(oxy)]bis(5,5-dimethylcyclohex-2-en-1-one)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 111.822(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.9184(13)
_cell_length_b                   6.5230(5)
_cell_length_c                   17.2645(11)
_cell_measurement_reflns_used    2235
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.71
_cell_measurement_theta_min      2.54
_cell_volume                     1768.8(2)
_computing_cell_refinement
;
SAINT (Bruker, 2018)
;
_computing_data_collection
;
APEX4 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2018)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10346
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.910
_diffrn_reflns_theta_min         2.542
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.200
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         2111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0452
_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)+(0.0456P)²+1.1303P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1180
_reflns_number_gt                1559
_reflns_number_total             2111
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            nx2010.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2023131
_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   0.974
_shelx_estimated_absorpt_t_max   0.986
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
O O1 0.44150(6) 0.32631(17) 0.28986(6) 0.0333(3) Uani d 1 . .
O O2 0.42054(9) 0.1572(2) 0.54805(7) 0.0545(4) Uani d 1 . .
C C6 0.30515(9) 0.5396(2) 0.39219(8) 0.0252(3) Uani d 1 . .
C C2 0.41732(8) 0.3534(2) 0.35542(8) 0.0264(3) Uani d 1 . .
C C3 0.43558(8) 0.2261(2) 0.42109(8) 0.0276(3) Uani d 1 . .
H H3 0.468878 0.106836 0.424213 0.033 Uiso calc 1 . .
C C7 0.36773(9) 0.5477(2) 0.34683(9) 0.0311(3) Uani d 1 . .
H H7A 0.335662 0.575102 0.286885 0.037 Uiso calc 1 . .
H H7B 0.407869 0.662711 0.369541 0.037 Uiso calc 1 . .
C C5 0.35360(9) 0.4640(2) 0.48148(8) 0.0296(3) Uani d 1 . .
H H5A 0.392750 0.573764 0.513085 0.036 Uiso calc 1 . .
H H5B 0.312185 0.439501 0.508610 0.036 Uiso calc 1 . .
C C4 0.40447(9) 0.2706(2) 0.48729(8) 0.0299(3) Uani d 1 . .
C C1 0.49293(9) 0.1495(3) 0.29054(9) 0.0316(4) Uani d 1 . .
H H1A 0.463346 0.022376 0.295832 0.038 Uiso calc 1 . .
H H1B 0.548105 0.157036 0.338214 0.038 Uiso calc 1 . .
C C8 0.23173(9) 0.3930(3) 0.34703(10) 0.0350(4) Uani d 1 . .
H H8A 0.201336 0.441546 0.289903 0.052 Uiso calc 1 . .
H H8B 0.192439 0.388104 0.376769 0.052 Uiso calc 1 . .
H H8C 0.254452 0.255480 0.345518 0.052 Uiso calc 1 . .
C C9 0.26825(12) 0.7527(3) 0.39343(10) 0.0429(4) Uani d 1 . .
H H9A 0.314317 0.847356 0.423877 0.064 Uiso calc 1 . .
H H9B 0.227197 0.745890 0.421145 0.064 Uiso calc 1 . .
H H9C 0.239567 0.801562 0.336078 0.064 Uiso calc 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'
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
C2 O1 C1 . . 117.88(10) ?
C9 C6 C8 . . 108.50(12) ?
C9 C6 C5 . . 110.31(11) ?
C8 C6 C5 . . 109.89(12) ?
C9 C6 C7 . . 109.84(12) ?
C8 C6 C7 . . 110.15(11) ?
C5 C6 C7 . . 108.15(11) ?
C3 C2 O1 . . 125.39(13) ?
C3 C2 C7 . . 123.44(12) ?
O1 C2 C7 . . 111.17(11) ?
C2 C3 C4 . . 120.14(13) ?
C2 C3 H3 . . 119.9 ?
C4 C3 H3 . . 119.9 ?
C2 C7 C6 . . 112.86(11) ?
C2 C7 H7A . . 109.0 ?
C6 C7 H7A . . 109.0 ?
C2 C7 H7B . . 109.0 ?
C6 C7 H7B . . 109.0 ?
H7A C7 H7B . . 107.8 ?
C4 C5 C6 . . 114.46(11) ?
C4 C5 H5A . . 108.6 ?
C6 C5 H5A . . 108.6 ?
C4 C5 H5B . . 108.6 ?
C6 C5 H5B . . 108.6 ?
H5A C5 H5B . . 107.6 ?
O2 C4 C3 . . 121.41(13) ?
O2 C4 C5 . . 119.97(12) ?
C3 C4 C5 . . 118.59(12) ?
O1 C1 C1 . 2_655 107.24(10) ?
O1 C1 H1A . . 110.3 ?
C1 C1 H1A 2_655 . 110.3 ?
O1 C1 H1B . . 110.3 ?
C1 C1 H1B 2_655 . 110.3 ?
H1A C1 H1B . . 108.5 ?
C6 C8 H8A . . 109.5 ?
C6 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C6 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C6 C9 H9A . . 109.5 ?
C6 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C6 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
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
O1 C2 . 1.3507(16) ?
O1 C1 . 1.4423(17) ?
O2 C4 . 1.2284(17) ?
C6 C9 . 1.527(2) ?
C6 C8 . 1.532(2) ?
C6 C5 . 1.5336(19) ?
C6 C7 . 1.5340(19) ?
C2 C3 . 1.3454(19) ?
C2 C7 . 1.496(2) ?
C3 C4 . 1.4543(18) ?
C3 H3 . 0.9500 ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C5 C4 . 1.5096(19) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C1 C1 2_655 1.505(3) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
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
C3 H3 O2 5_656 0.95 2.46 3.391(2) 168 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
C1 O1 C2 C3 . . . . -1.6(2) ?
C1 O1 C2 C7 . . . . 177.57(12) ?
O1 C2 C3 C4 . . . . -178.91(13) ?
C7 C2 C3 C4 . . . . 2.0(2) ?
C3 C2 C7 C6 . . . . -28.0(2) ?
O1 C2 C7 C6 . . . . 152.85(12) ?
C9 C6 C7 C2 . . . . 170.39(13) ?
C8 C6 C7 C2 . . . . -70.16(15) ?
C5 C6 C7 C2 . . . . 49.95(16) ?
C9 C6 C5 C4 . . . . -170.57(13) ?
C8 C6 C5 C4 . . . . 69.86(16) ?
C7 C6 C5 C4 . . . . -50.42(16) ?
C2 C3 C4 O2 . . . . -179.70(15) ?
C2 C3 C4 C5 . . . . -1.5(2) ?
C6 C5 C4 O2 . . . . -154.38(15) ?
C6 C5 C4 C3 . . . . 27.4(2) ?
C2 O1 C1 C1 . . . 2_655 177.15(12) ?
