#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/50/2235096.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_2235096
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Lim, Ming Yeng'
'Quah, Ching Kheng'
'Wu, Dongdong'
_publ_section_title
;
 1,1'-Bicyclohexyl-1,1'-diyl 2,2'-bipyridine-3,3'-dicarboxylate
;
_journal_coeditor_code           IS5124
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1629
_journal_paper_doi               10.1107/S1600536812018508
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C24 H26 N2 O4'
_chemical_formula_moiety         'C24 H26 N2 O4'
_chemical_formula_sum            'C24 H26 N2 O4'
_chemical_formula_weight         406.47
_chemical_name_common
;
7,8-Dispirohexyl-7,8-dihydro-[1,4]dioxecino[7,6-b:8,9-b']dipyridine-5,10-dione
;
_chemical_name_systematic
;
1,1'-Bicyclohexyl-1,1'-diyl 2,2'-bipyridine-3,3'-dicarboxylate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                90.00
_cell_angle_beta                 99.8100(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.7647(3)
_cell_length_b                   10.2618(2)
_cell_length_c                   11.5755(2)
_cell_measurement_reflns_used    4821
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.42
_cell_measurement_theta_min      2.34
_cell_volume                     1962.28(6)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
;
Bruker SMART APEXII 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  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11734
_diffrn_reflns_theta_full        32.66
_diffrn_reflns_theta_max         32.66
_diffrn_reflns_theta_min         2.34
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_correction_T_min  0.9523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.525
_exptl_crystal_size_mid          0.242
_exptl_crystal_size_min          0.121
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.266
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         3578
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0602P)²+1.2358P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1194
_reflns_number_gt                2972
_reflns_number_total             3578
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is5124.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2235096
_cod_database_fobs_code          2235096
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.07035(4) 0.91569(6) 0.32195(5) 0.01138(14) Uani d . 1 1
O O2 0.08919(4) 0.79994(7) 0.15933(6) 0.01480(15) Uani d . 1 1
N N1 0.03750(5) 0.47163(8) 0.36731(7) 0.01641(17) Uani d . 1 1
C C1 0.13527(6) 0.68507(10) 0.44475(8) 0.01575(18) Uani d . 1 1
H H1A 0.1678 0.7583 0.4717 0.019 Uiso calc R 1 1
C C2 0.13993(6) 0.57190(10) 0.51086(8) 0.01792(19) Uani d . 1 1
H H2A 0.1757 0.5658 0.5837 0.022 Uiso calc R 1 1
C C3 0.09090(6) 0.46750(10) 0.46771(8) 0.01813(19) Uani d . 1 1
H H3A 0.0955 0.3889 0.5117 0.022 Uiso calc R 1 1
C C4 0.03211(5) 0.58187(9) 0.30384(8) 0.01315(17) Uani d . 1 1
C C5 0.08212(5) 0.68998(9) 0.33802(8) 0.01229(16) Uani d . 1 1
C C6 0.08110(5) 0.80731(9) 0.26097(8) 0.01163(16) Uani d . 1 1
C C7 0.04781(5) 1.04426(9) 0.26757(7) 0.01063(16) Uani d . 1 1
C C8 0.09239(5) 1.07527(9) 0.16519(8) 0.01365(17) Uani d . 1 1
H H8A 0.0760 1.0116 0.1013 0.016 Uiso calc R 1 1
H H8B 0.0764 1.1631 0.1343 0.016 Uiso calc R 1 1
C C9 0.18467(6) 1.07060(10) 0.20256(9) 0.01769(19) Uani d . 1 1
H H9A 0.2013 0.9814 0.2289 0.021 Uiso calc R 1 1
H H9B 0.2110 1.0921 0.1346 0.021 Uiso calc R 1 1
C C10 0.21245(6) 1.16711(11) 0.30191(9) 0.0207(2) Uani d . 1 1
H H10A 0.2716 1.1591 0.3280 0.025 Uiso calc R 1 1
H H10B 0.2007 1.2572 0.2734 0.025 Uiso calc R 1 1
C C11 0.16867(6) 1.13963(10) 0.40464(8) 0.01758(19) Uani d . 1 1
H H11A 0.1842 1.2065 0.4660 0.021 Uiso calc R 1 1
H H11B 0.1860 1.0537 0.4388 0.021 Uiso calc R 1 1
C C12 0.07650(5) 1.14012(9) 0.36753(8) 0.01346(17) Uani d . 1 1
H H12A 0.0585 1.2291 0.3422 0.016 Uiso calc R 1 1
H H12B 0.0510 1.1171 0.4359 0.016 Uiso calc R 1 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_3
_geom_angle
C6 O1 C7 . 124.05(6)
C3 N1 C4 . 118.24(9)
C2 C1 C5 . 119.12(9)
C2 C1 H1A . 120.4
C5 C1 H1A . 120.4
C1 C2 C3 . 118.24(9)
C1 C2 H2A . 120.9
C3 C2 H2A . 120.9
N1 C3 C2 . 123.60(9)
N1 C3 H3A . 118.2
C2 C3 H3A . 118.2
N1 C4 C5 . 121.94(8)
N1 C4 C4 2 115.20(6)
C5 C4 C4 2 122.84(6)
C1 C5 C4 . 118.74(8)
C1 C5 C6 . 119.82(8)
C4 C5 C6 . 121.42(8)
O2 C6 O1 . 127.53(8)
O2 C6 C5 . 122.52(8)
O1 C6 C5 . 109.95(7)
O1 C7 C12 . 103.07(6)
O1 C7 C8 . 112.90(7)
C12 C7 C8 . 108.53(7)
O1 C7 C7 2 106.40(5)
C12 C7 C7 2 111.54(7)
C8 C7 C7 2 113.91(8)
C9 C8 C7 . 112.04(7)
C9 C8 H8A . 109.2
C7 C8 H8A . 109.2
C9 C8 H8B . 109.2
C7 C8 H8B . 109.2
H8A C8 H8B . 107.9
C10 C9 C8 . 110.80(8)
C10 C9 H9A . 109.5
C8 C9 H9A . 109.5
C10 C9 H9B . 109.5
C8 C9 H9B . 109.5
H9A C9 H9B . 108.1
C11 C10 C9 . 109.94(8)
C11 C10 H10A . 109.7
C9 C10 H10A . 109.7
C11 C10 H10B . 109.7
C9 C10 H10B . 109.7
H10A C10 H10B . 108.2
C10 C11 C12 . 112.15(8)
C10 C11 H11A . 109.2
C12 C11 H11A . 109.2
C10 C11 H11B . 109.2
C12 C11 H11B . 109.2
H11A C11 H11B . 107.9
C11 C12 C7 . 112.42(8)
C11 C12 H12A . 109.1
C7 C12 H12A . 109.1
C11 C12 H12B . 109.1
C7 C12 H12B . 109.1
H12A C12 H12B . 107.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C6 . 1.3458(11)
O1 C7 . 1.4828(11)
O2 C6 . 1.2094(11)
N1 C3 . 1.3414(12)
N1 C4 . 1.3435(12)
C1 C2 . 1.3856(14)
C1 C5 . 1.3956(12)
C1 H1A . 0.9500
C2 C3 . 1.3903(15)
C2 H2A . 0.9500
C3 H3A . 0.9500
C4 C5 . 1.4061(13)
C4 C4 2 1.5018(18)
C5 C6 . 1.4968(12)
C7 C12 . 1.5324(12)
C7 C8 . 1.5382(12)
C7 C7 2 1.5854(17)
C8 C9 . 1.5344(13)
C8 H8A . 0.9900
C8 H8B . 0.9900
C9 C10 . 1.5290(15)
C9 H9A . 0.9900
C9 H9B . 0.9900
C10 C11 . 1.5264(15)
C10 H10A . 0.9900
C10 H10B . 0.9900
C11 C12 . 1.5317(13)
C11 H11A . 0.9900
C11 H11B . 0.9900
C12 H12A . 0.9900
C12 H12B . 0.9900
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 H3A O2 6_566 0.95 2.60 3.5319(12) 168 yes
C12 H12A N1 1_565 0.99 2.54 3.4641(12) 156 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_4
_geom_torsion
C5 C1 C2 C3 . . -0.15(14)
C4 N1 C3 C2 . . 1.26(15)
C1 C2 C3 N1 . . -2.13(16)
C3 N1 C4 C5 . . 1.90(14)
C3 N1 C4 C4 . 2 -176.74(10)
C2 C1 C5 C4 . . 3.07(14)
C2 C1 C5 C6 . . -175.08(8)
N1 C4 C5 C1 . . -4.06(14)
C4 C4 C5 C1 2 . 174.47(10)
N1 C4 C5 C6 . . 174.05(8)
C4 C4 C5 C6 2 . -7.41(15)
C7 O1 C6 O2 . . 14.66(13)
C7 O1 C6 C5 . . -165.46(7)
C1 C5 C6 O2 . . 126.10(10)
C4 C5 C6 O2 . . -52.00(13)
C1 C5 C6 O1 . . -53.79(11)
C4 C5 C6 O1 . . 128.11(9)
C6 O1 C7 C12 . . -157.78(7)
C6 O1 C7 C8 . . -40.90(10)
C6 O1 C7 C7 . 2 84.75(10)
O1 C7 C8 C9 . . -56.99(10)
C12 C7 C8 C9 . . 56.61(10)
C7 C7 C8 C9 2 . -178.48(6)
C7 C8 C9 C10 . . -58.49(11)
C8 C9 C10 C11 . . 56.01(11)
C9 C10 C11 C12 . . -54.88(11)
C10 C11 C12 C7 . . 55.67(11)
O1 C7 C12 C11 . . 65.03(9)
C8 C7 C12 C11 . . -54.90(10)
C7 C7 C12 C11 2 . 178.81(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101566285
