#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:00:13 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301809 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/13/2311381.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_2311381
loop_
_publ_author_name
'Sim, Aijia'
'Chidan Kumar, C. S.'
'Kwong, Huey Chong'
'Then, Li Yee'
'Win, Yip-Foo'
'Quah, Ching Kheng'
'Naveen, S.'
'Chandraju, S.'
'Lokanath, N. K.'
'Warad, Ismail'
_publ_section_title
;
 Three closely related
 (2E,2'E)-3,3'-(1,4-phenyl-ene)bis-[1-(meth-oxy-phen-yl)prop-2-en-1-ones]:
 supra-molecular assemblies in one dimension mediated by hydrogen bonding
 and C-H⋯π inter-actions.
;
_journal_coeditor_code           HB7678
_journal_issue                   'Pt 6'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              896
_journal_page_last               900
_journal_paper_doi               10.1107/S2056989017007460
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C26 H22 O4'
_chemical_formula_moiety         'C26 H22 O4'
_chemical_formula_sum            'C26 H22 O4'
_chemical_formula_weight         398.43
_chemical_name_systematic
(2E,2'E)-3,3'-(1,4-Phenylene)bis[1-(3-methoxyphenyl)prop-2-en-1-one]
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 98.760(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.2626(5)
_cell_length_b                   15.6157(14)
_cell_length_c                   12.4824(11)
_cell_measurement_reflns_used    2940
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.71
_cell_measurement_theta_min      2.61
_cell_volume                     1013.83(16)
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
SHELXL2013 (Sheldrick, 2015) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material
;
SHELXL2013 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Bruker APEXII DUO CCD area-detector
;
_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  0.0425
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17791
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.081
_diffrn_reflns_theta_min         2.104
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       needle
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.898
_exptl_crystal_size_mid          0.477
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2458
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0436
_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)+(0.0567P)²+0.1380P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1320
_reflns_number_gt                1574
_reflns_number_total             2458
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7678sup1.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2311381
_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   0.926
_shelx_estimated_absorpt_t_max   0.992
_shelxl_version_number           20.13
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_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
O O1 1.3466(2) 0.50160(7) 0.83740(9) 0.0753(4) Uani d 1
O O2 2.0704(2) 0.69588(8) 1.00094(10) 0.0771(4) Uani d 1
C C1 1.6959(3) 0.63162(9) 0.89251(12) 0.0502(4) Uani d 1
H H1A 1.6962 0.5856 0.9399 0.060 Uiso calc 1
C C2 1.8795(3) 0.69465(10) 0.91308(12) 0.0552(4) Uani d 1
C C3 1.8786(3) 0.76279(11) 0.84322(15) 0.0680(5) Uani d 1
H H3A 2.0034 0.8052 0.8572 0.082 Uiso calc 1
C C4 1.6943(3) 0.76859(11) 0.75284(16) 0.0723(5) Uani d 1
H H4A 1.6945 0.8150 0.7062 0.087 Uiso calc 1
C C5 1.5086(3) 0.70582(10) 0.73089(13) 0.0583(4) Uani d 1
H H5A 1.3841 0.7100 0.6697 0.070 Uiso calc 1
C C6 1.5086(3) 0.63679(9) 0.80022(11) 0.0461(3) Uani d 1
C C7 1.3200(3) 0.56519(9) 0.78002(11) 0.0499(4) Uani d 1
C C8 1.1041(3) 0.57169(10) 0.69022(12) 0.0525(4) Uani d 1
H H8A 1.0879 0.6207 0.6473 0.063 Uiso calc 1
C C9 0.9345(3) 0.51020(9) 0.66922(11) 0.0505(4) Uani d 1
H H9A 0.9579 0.4629 0.7149 0.061 Uiso calc 1
C C10 0.7126(2) 0.50652(9) 0.58281(10) 0.0450(3) Uani d 1
C C11 0.6491(3) 0.57310(9) 0.50998(11) 0.0514(4) Uani d 1
H H11A 0.7478 0.6228 0.5161 0.062 Uiso calc 1
C C12 0.5587(3) 0.43363(10) 0.57116(11) 0.0522(4) Uani d 1
H H12A 0.5971 0.3884 0.6194 0.063 Uiso calc 1
C C13 2.1228(4) 0.61900(12) 1.05960(15) 0.0766(6) Uani d 1
H H13A 2.2657 0.6275 1.1163 0.115 Uiso calc 1
H H13B 2.1640 0.5748 1.0117 0.115 Uiso calc 1
H H13C 1.9743 0.6024 1.0908 0.115 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
C2 O2 C13 . 117.70(12)
C2 C1 C6 . 119.92(14)
C2 C1 H1A . 120.0
C6 C1 H1A . 120.0
O2 C2 C3 . 115.34(13)
O2 C2 C1 . 124.61(14)
C3 C2 C1 . 120.05(14)
C4 C3 C2 . 120.36(15)
C4 C3 H3A . 119.8
C2 C3 H3A . 119.8
C3 C4 C5 . 120.36(16)
C3 C4 H4A . 119.8
C5 C4 H4A . 119.8
C4 C5 C6 . 119.78(14)
C4 C5 H5A . 120.1
C6 C5 H5A . 120.1
C5 C6 C1 . 119.53(13)
C5 C6 C7 . 122.86(12)
C1 C6 C7 . 117.59(13)
O1 C7 C8 . 120.62(13)
O1 C7 C6 . 119.81(12)
C8 C7 C6 . 119.57(13)
C9 C8 C7 . 121.65(14)
C9 C8 H8A . 119.2
C7 C8 H8A . 119.2
C8 C9 C10 . 128.20(14)
C8 C9 H9A . 115.9
C10 C9 H9A . 115.9
C11 C10 C12 . 117.76(12)
C11 C10 C9 . 122.57(13)
C12 C10 C9 . 119.67(13)
C12 C11 C10 3_666 120.65(13)
C12 C11 H11A 3_666 119.7
C10 C11 H11A . 119.7
C11 C12 C10 3_666 121.59(13)
C11 C12 H12A 3_666 119.2
C10 C12 H12A . 119.2
O2 C13 H13A . 109.5
O2 C13 H13B . 109.5
H13A C13 H13B . 109.5
O2 C13 H13C . 109.5
H13A C13 H13C . 109.5
H13B C13 H13C . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C7 . 1.2199(17)
O2 C2 . 1.3698(17)
O2 C13 . 1.411(2)
C1 C2 . 1.376(2)
C1 C6 . 1.3998(18)
C1 H1A . 0.9300
C2 C3 . 1.375(2)
C3 C4 . 1.374(2)
C3 H3A . 0.9300
C4 C5 . 1.382(2)
C4 H4A . 0.9300
C5 C6 . 1.382(2)
C5 H5A . 0.9300
C6 C7 . 1.491(2)
C7 C8 . 1.4729(18)
C8 C9 . 1.310(2)
C8 H8A . 0.9300
C9 C10 . 1.4652(17)
C9 H9A . 0.9300
C10 C11 . 1.3882(19)
C10 C12 . 1.392(2)
C11 C12 3_666 1.3765(18)
C11 H11A . 0.9300
C12 C11 3_666 1.3766(18)
C12 H12A . 0.9300
C13 H13A . 0.9600
C13 H13B . 0.9600
C13 H13C . 0.9600
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_4
_geom_torsion
C13 O2 C2 C3 . -164.12(17)
C13 O2 C2 C1 . 16.2(2)
C6 C1 C2 O2 . 179.81(14)
C6 C1 C2 C3 . 0.2(2)
O2 C2 C3 C4 . -179.41(16)
C1 C2 C3 C4 . 0.3(3)
C2 C3 C4 C5 . -0.3(3)
C3 C4 C5 C6 . 0.0(3)
C4 C5 C6 C1 . 0.5(2)
C4 C5 C6 C7 . -177.93(16)
C2 C1 C6 C5 . -0.5(2)
C2 C1 C6 C7 . 177.94(14)
C5 C6 C7 O1 . 171.91(15)
C1 C6 C7 O1 . -6.5(2)
C5 C6 C7 C8 . -7.6(2)
C1 C6 C7 C8 . 173.97(13)
O1 C7 C8 C9 . 0.2(2)
C6 C7 C8 C9 . 179.71(14)
C7 C8 C9 C10 . -179.20(14)
C8 C9 C10 C11 . -1.7(2)
C8 C9 C10 C12 . 177.64(16)
C12 C10 C11 C12 3_666 -0.4(2)
C9 C10 C11 C12 3_666 178.90(14)
C11 C10 C12 C11 3_666 0.4(2)
C9 C10 C12 C11 3_666 -178.91(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 90655479
