#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/66/2226685.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_2226685
loop_
_publ_author_name
'Zhang, Rui-Long'
'Liu, Zhao-Di'
'Wu, Jie-Ying'
_publ_section_title
;
 2,2'-[(1E,1'E)-2,2'-(2,5-Dibutoxy-1,4-phenylene)bis(ethene-2,1-diyl)]dipyridine
;
_journal_coeditor_code           SU2172
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1877
_journal_paper_doi               10.1107/S1600536810013656
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C28 H32 N2 O2'
_chemical_formula_moiety         'C28 H32 N2 O2'
_chemical_formula_sum            'C28 H32 N2 O2'
_chemical_formula_weight         428.56
_chemical_name_systematic
;
2,2'-[(1E,1'E)-2,2'-(2,5-Dibutoxy-1,4-phenylene)bis(ethene-
2,1-diyl)]dipyridine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 107.392(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            2
_cell_length_a                   8.882(5)
_cell_length_b                   13.892(5)
_cell_length_c                   10.387(5)
_cell_measurement_reflns_used    1446
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.77
_cell_measurement_theta_min      2.52
_cell_volume                     1223.0(10)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8512
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.40
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9856
_exptl_absorpt_correction_T_min  0.9644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2162
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0821P)²+0.0525P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1539
_reflns_number_gt                1385
_reflns_number_total             2162
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2172.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226685
_cod_database_fobs_code          2226685
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.10160(17) 0.50961(9) 0.22161(12) 0.0589(4) Uani d . 1 . .
C C2 0.0431(2) 0.57863(13) 0.43825(17) 0.0477(5) Uani d . 1 . .
H H2 0.0725 0.6313 0.3960 0.057 Uiso calc R 1 . .
C C1 -0.0472(2) 0.50707(13) 0.36022(17) 0.0458(5) Uani d . 1 . .
C C5 0.2548(2) 0.72369(13) 0.61936(18) 0.0491(5) Uani d . 1 . .
H H5 0.2324 0.7310 0.5265 0.059 Uiso calc R 1 . .
C C4 0.1898(2) 0.64922(13) 0.66286(18) 0.0487(5) Uani d . 1 . .
H H4 0.2083 0.6442 0.7556 0.058 Uiso calc R 1 . .
C C6 0.3587(2) 0.79507(14) 0.70512(19) 0.0500(5) Uani d . 1 . .
C C3 0.0919(2) 0.57414(13) 0.57915(17) 0.0447(5) Uani d . 1 . .
N N1 0.3841(2) 0.78919(14) 0.83829(17) 0.0781(6) Uani d . 1 . .
C C7 0.4305(3) 0.86549(15) 0.6486(2) 0.0617(6) Uani d . 1 . .
H H7 0.4106 0.8689 0.5556 0.074 Uiso calc R 1 . .
C C11 -0.0751(3) 0.59382(15) 0.15295(19) 0.0620(6) Uani d . 1 . .
H H11A 0.0359 0.5996 0.1601 0.074 Uiso calc R 1 . .
H H11B -0.1069 0.6507 0.1922 0.074 Uiso calc R 1 . .
C C12 -0.1717(3) 0.58404(16) 0.00746(18) 0.0639(6) Uani d . 1 . .
H H12A -0.1503 0.5217 -0.0253 0.077 Uiso calc R 1 . .
H H12B -0.2826 0.5857 0.0020 0.077 Uiso calc R 1 . .
C C8 0.5312(3) 0.93013(17) 0.7318(3) 0.0770(7) Uani d . 1 . .
H H8 0.5797 0.9780 0.6957 0.092 Uiso calc R 1 . .
C C10 0.4832(3) 0.8533(2) 0.9145(2) 0.0988(10) Uani d . 1 . .
H H10 0.5018 0.8498 1.0074 0.119 Uiso calc R 1 . .
C C9 0.5588(3) 0.9232(2) 0.8671(3) 0.0907(9) Uani d . 1 . .
H H9 0.6277 0.9652 0.9258 0.109 Uiso calc R 1 . .
C C13 -0.1405(4) 0.6606(2) -0.0831(2) 0.0963(9) Uani d . 1 . .
H H13A -0.0302 0.6582 -0.0795 0.116 Uiso calc R 1 . .
H H13B -0.1603 0.7231 -0.0499 0.116 Uiso calc R 1 . .
C C14 -0.2407(4) 0.6502(2) -0.2276(2) 0.0996(10) Uani d . 1 . .
H H14A -0.2273 0.5868 -0.2594 0.149 Uiso calc R 1 . .
H H14B -0.2092 0.6972 -0.2822 0.149 Uiso calc R 1 . .
H H14C -0.3496 0.6599 -0.2335 0.149 Uiso calc R 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'
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
C1 O1 C11 . . 119.07(14) ?
C1 C2 C3 . . 121.80(18) ?
C1 C2 H2 . . 119.1 ?
C3 C2 H2 . . 119.1 ?
O1 C1 C2 . . 123.88(17) ?
O1 C1 C3 . 3_566 115.58(15) ?
C2 C1 C3 . 3_566 120.53(17) ?
C4 C5 C6 . . 125.48(18) ?
C4 C5 H5 . . 117.3 ?
C6 C5 H5 . . 117.3 ?
C5 C4 C3 . . 126.43(18) ?
C5 C4 H4 . . 116.8 ?
C3 C4 H4 . . 116.8 ?
N1 C6 C7 . . 121.57(18) ?
N1 C6 C5 . . 118.03(18) ?
C7 C6 C5 . . 120.38(18) ?
C2 C3 C1 . 3_566 117.66(16) ?
C2 C3 C4 . . 122.17(17) ?
C1 C3 C4 3_566 . 120.15(16) ?
C10 N1 C6 . . 116.8(2) ?
C8 C7 C6 . . 119.3(2) ?
C8 C7 H7 . . 120.4 ?
C6 C7 H7 . . 120.4 ?
O1 C11 C12 . . 107.37(16) ?
O1 C11 H11A . . 110.2 ?
C12 C11 H11A . . 110.2 ?
O1 C11 H11B . . 110.2 ?
C12 C11 H11B . . 110.2 ?
H11A C11 H11B . . 108.5 ?
C13 C12 C11 . . 114.19(19) ?
C13 C12 H12A . . 108.7 ?
C11 C12 H12A . . 108.7 ?
C13 C12 H12B . . 108.7 ?
C11 C12 H12B . . 108.7 ?
H12A C12 H12B . . 107.6 ?
C9 C8 C7 . . 119.1(2) ?
C9 C8 H8 . . 120.4 ?
C7 C8 H8 . . 120.4 ?
N1 C10 C9 . . 125.0(2) ?
N1 C10 H10 . . 117.5 ?
C9 C10 H10 . . 117.5 ?
C10 C9 C8 . . 118.2(2) ?
C10 C9 H9 . . 120.9 ?
C8 C9 H9 . . 120.9 ?
C12 C13 C14 . . 113.1(2) ?
C12 C13 H13A . . 109.0 ?
C14 C13 H13A . . 109.0 ?
C12 C13 H13B . . 109.0 ?
C14 C13 H13B . . 109.0 ?
H13A C13 H13B . . 107.8 ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 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
_geom_bond_publ_flag
O1 C1 . 1.375(2) ?
O1 C11 . 1.426(2) ?
C2 C1 . 1.379(3) ?
C2 C3 . 1.398(2) ?
C2 H2 . 0.9300 ?
C1 C3 3_566 1.406(3) ?
C5 C4 . 1.328(3) ?
C5 C6 . 1.462(3) ?
C5 H5 . 0.9300 ?
C4 C3 . 1.466(3) ?
C4 H4 . 0.9300 ?
C6 N1 . 1.336(2) ?
C6 C7 . 1.390(3) ?
C3 C1 3_566 1.406(3) ?
N1 C10 . 1.334(3) ?
C7 C8 . 1.375(3) ?
C7 H7 . 0.9300 ?
C11 C12 . 1.504(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.499(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C8 C9 . 1.356(3) ?
C8 H8 . 0.9300 ?
C10 C9 . 1.353(3) ?
C10 H10 . 0.9300 ?
C9 H9 . 0.9300 ?
C13 C14 . 1.506(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
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
C5 H5 N1 4_575 0.93 2.70 3.446(3) 138
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102232281
