#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:00:13 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301809 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/13/2311382.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_2311382
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          'C28 H26 O6'
_chemical_formula_moiety         'C28 H26 O6'
_chemical_formula_sum            'C28 H26 O6'
_chemical_formula_weight         458.49
_chemical_name_systematic
(2E,2'E)-3,3'-(1,4-Phenylene)bis[1-(3,4-dimethoxyphenyl)prop-2-en-1-one]
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 103.602(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.9595(6)
_cell_length_b                   21.0272(17)
_cell_length_c                   8.3297(7)
_cell_measurement_reflns_used    3549
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.54
_cell_measurement_theta_min      2.70
_cell_volume                     1184.77(17)
_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 0.996
_diffrn_measured_fraction_theta_max 0.997
_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  0.0298
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12532
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.044
_diffrn_reflns_theta_min         1.937
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.352
_exptl_crystal_size_mid          0.266
_exptl_crystal_size_min          0.163
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0487
_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)+(0.0557P)²+0.2808P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1358
_reflns_number_gt                2328
_reflns_number_total             3165
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7678sup1.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2311382
_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   0.969
_shelx_estimated_absorpt_t_max   0.985
_shelxl_version_number           20.13
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
O O1 0.26810(16) 0.04480(7) 0.05640(13) 0.0667(4) Uani d 1
O O2 -0.37696(15) 0.15896(5) 0.01870(14) 0.0560(3) Uani d 1
O O3 -0.33472(18) 0.22511(6) 0.28240(17) 0.0694(4) Uani d 1
C C1 -0.04399(19) 0.11677(6) 0.10365(16) 0.0377(3) Uani d 1
H H1A -0.0610 0.0919 0.0090 0.045 Uiso calc 1
C C2 -0.1959(2) 0.15447(6) 0.12601(17) 0.0399(3) Uani d 1
C C3 -0.1726(2) 0.19126(7) 0.2696(2) 0.0459(3) Uani d 1
C C4 0.0049(2) 0.19044(7) 0.3851(2) 0.0525(4) Uani d 1
H H4A 0.0217 0.2154 0.4796 0.063 Uiso calc 1
C C5 0.1585(2) 0.15265(7) 0.36105(18) 0.0469(4) Uani d 1
H H5A 0.2779 0.1525 0.4398 0.056 Uiso calc 1
C C6 0.13686(19) 0.11510(6) 0.22134(16) 0.0369(3) Uani d 1
C C7 0.2924(2) 0.07224(7) 0.18910(16) 0.0413(3) Uani d 1
C C8 0.4765(2) 0.06233(7) 0.31697(16) 0.0419(3) Uani d 1
H H8A 0.4879 0.0794 0.4218 0.050 Uiso calc 1
C C9 0.62488(19) 0.02971(7) 0.28517(16) 0.0385(3) Uani d 1
H H9A 0.6062 0.0140 0.1782 0.046 Uiso calc 1
C C10 0.81526(18) 0.01514(6) 0.39711(15) 0.0348(3) Uani d 1
C C11 0.8724(2) 0.03954(7) 0.55600(16) 0.0422(3) Uani d 1
H H11A 0.7872 0.0664 0.5947 0.051 Uiso calc 1
C C12 0.9466(2) -0.02452(7) 0.34276(16) 0.0429(3) Uani d 1
H H12A 0.9117 -0.0412 0.2364 0.051 Uiso calc 1
C C13 -0.4046(3) 0.12540(11) -0.1316(2) 0.0727(6) Uani d 1
H H13A -0.5375 0.1316 -0.1950 0.109 Uiso calc 1
H H13B -0.3816 0.0809 -0.1092 0.109 Uiso calc 1
H H13C -0.3135 0.1409 -0.1929 0.109 Uiso calc 1
C C14 -0.3309(3) 0.25570(12) 0.4350(3) 0.0920(8) Uani d 1
H H14A -0.4595 0.2727 0.4331 0.138 Uiso calc 1
H H14B -0.2360 0.2896 0.4516 0.138 Uiso calc 1
H H14C -0.2948 0.2255 0.5234 0.138 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 . 117.30(12)
C3 O3 C14 . 117.82(15)
C2 C1 C6 . 120.95(13)
C2 C1 H1A . 119.5
C6 C1 H1A . 119.5
O2 C2 C1 . 125.04(13)
O2 C2 C3 . 115.10(12)
C1 C2 C3 . 119.85(12)
O3 C3 C4 . 125.24(14)
O3 C3 C2 . 115.11(13)
C4 C3 C2 . 119.65(13)
C3 C4 C5 . 120.21(14)
C3 C4 H4A . 119.9
C5 C4 H4A . 119.9
C4 C5 C6 . 120.91(13)
C4 C5 H5A . 119.5
C6 C5 H5A . 119.5
C5 C6 C1 . 118.41(12)
C5 C6 C7 . 124.03(12)
C1 C6 C7 . 117.55(12)
O1 C7 C8 . 119.85(12)
O1 C7 C6 . 119.98(12)
C8 C7 C6 . 120.17(12)
C9 C8 C7 . 121.13(12)
C9 C8 H8A . 119.4
C7 C8 H8A . 119.4
C8 C9 C10 . 128.07(12)
C8 C9 H9A . 116.0
C10 C9 H9A . 116.0
C11 C10 C12 . 118.04(11)
C11 C10 C9 . 122.96(12)
C12 C10 C9 . 119.00(12)
C12 C11 C10 3_756 120.96(13)
C12 C11 H11A 3_756 119.5
C10 C11 H11A . 119.5
C11 C12 C10 3_756 121.00(12)
C11 C12 H12A 3_756 119.5
C10 C12 H12A . 119.5
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
O3 C14 H14A . 109.5
O3 C14 H14B . 109.5
H14A C14 H14B . 109.5
O3 C14 H14C . 109.5
H14A C14 H14C . 109.5
H14B C14 H14C . 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 . 1.2229(17)
O2 C2 . 1.3660(16)
O2 C13 . 1.410(2)
O3 C3 . 1.3593(18)
O3 C14 . 1.419(2)
C1 C2 . 1.3688(19)
C1 C6 . 1.4022(18)
C1 H1A . 0.9300
C2 C3 . 1.401(2)
C3 C4 . 1.376(2)
C4 C5 . 1.384(2)
C4 H4A . 0.9300
C5 C6 . 1.3848(19)
C5 H5A . 0.9300
C6 C7 . 1.4807(19)
C7 C8 . 1.4756(17)
C8 C9 . 1.318(2)
C8 H8A . 0.9300
C9 C10 . 1.4621(16)
C9 H9A . 0.9300
C10 C11 . 1.3877(18)
C10 C12 . 1.3893(19)
C11 C12 3_756 1.3781(18)
C11 H11A . 0.9300
C12 C11 3_756 1.3780(18)
C12 H12A . 0.9300
C13 H13A . 0.9600
C13 H13B . 0.9600
C13 H13C . 0.9600
C14 H14A . 0.9600
C14 H14B . 0.9600
C14 H14C . 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 C1 . -4.5(2)
C13 O2 C2 C3 . 176.83(15)
C6 C1 C2 O2 . -179.73(13)
C6 C1 C2 C3 . -1.1(2)
C14 O3 C3 C4 . -8.5(3)
C14 O3 C3 C2 . 170.79(17)
O2 C2 C3 O3 . 1.14(19)
C1 C2 C3 O3 . -177.63(13)
O2 C2 C3 C4 . -179.52(14)
C1 C2 C3 C4 . 1.7(2)
O3 C3 C4 C5 . 178.13(15)
C2 C3 C4 C5 . -1.1(2)
C3 C4 C5 C6 . 0.0(2)
C4 C5 C6 C1 . 0.7(2)
C4 C5 C6 C7 . -178.35(14)
C2 C1 C6 C5 . -0.1(2)
C2 C1 C6 C7 . 178.99(13)
C5 C6 C7 O1 . -173.70(15)
C1 C6 C7 O1 . 7.3(2)
C5 C6 C7 C8 . 6.5(2)
C1 C6 C7 C8 . -172.50(13)
O1 C7 C8 C9 . 7.3(2)
C6 C7 C8 C9 . -172.95(14)
C7 C8 C9 C10 . -179.46(13)
C8 C9 C10 C11 . -5.6(2)
C8 C9 C10 C12 . 174.89(15)
C12 C10 C11 C12 3_756 -0.4(2)
C9 C10 C11 C12 3_756 -179.97(14)
C11 C10 C12 C11 3_756 0.4(2)
C9 C10 C12 C11 3_756 179.98(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 90655480
