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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/39/4503951.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
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data_4503951
loop_
_publ_author_name
'Scott, Janet L.'
'Almesaker, Ann'
'Sumi, Yoshinori'
'Tanaka, Koichi'
_publ_section_title
;
 Guest Signaling
 Compound: trans-3,3‘-Bis(diphenylhydroxymethyl)azobenzene
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1049
_journal_paper_doi               10.1021/cg060522b
_journal_volume                  7
_journal_year                    2007
_chemical_formula_sum            'C24 H20 N2 O'
_chemical_formula_weight         352.42
_chemical_name_systematic
; 
 (E)-(3,3'-(diazene-1,2-diyl)bis(3,1-phenylene))bis(diphenylmethanol) pyridine solvate 
;
_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                90.00
_cell_angle_beta                 112.545(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1808(6)
_cell_length_b                   23.8820(10)
_cell_length_c                   9.2981(5)
_cell_measurement_temperature    123(2)
_cell_volume                     1882.87(18)
_computing_cell_refinement       'Nonius collect'
_computing_data_collection       'Nonius collect'
_computing_data_reduction        'Nonius collect'
_computing_molecular_graphics    X-Seed
_computing_publication_material  ciftab
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Enraf Nonius Kappa CCD'
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0929
_diffrn_reflns_av_sigmaI/netI    0.1695
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8119
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4474
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.912
_refine_ls_R_factor_all          0.1908
_refine_ls_R_factor_gt           0.0582
_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)+(0.0574P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1425
_reflns_number_gt                1845
_reflns_number_total             4474
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060522bsi20060803_014632.cif
_cod_data_source_block           2.2pyridine
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4503951
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.78860(17) 0.17021(6) 0.08411(18) 0.0294(4) Uani 1 1 d .
C1 C 0.5579(2) 0.05833(10) -0.3697(2) 0.0237(5) Uani 1 1 d .
C7 C 0.6869(2) 0.12222(10) 0.0391(2) 0.0234(5) Uani 1 1 d .
N1 N 0.5228(2) 0.00221(8) -0.42722(18) 0.0299(5) Uani 1 1 d .
C21 C 0.7789(2) 0.07127(10) 0.1297(2) 0.0238(5) Uani 1 1 d .
C3 C 0.6422(2) 0.11544(10) -0.1371(2) 0.0237(6) Uani 1 1 d .
C2 C 0.6045(2) 0.06351(10) -0.2095(2) 0.0245(6) Uani 1 1 d .
H2 H 0.6108 0.0310 -0.1484 0.029 Uiso 1 1 calc R
C11 C 0.5351(2) 0.13355(10) 0.0688(2) 0.0236(6) Uani 1 1 d .
C4 C 0.6328(3) 0.16181(10) -0.2294(3) 0.0330(6) Uani 1 1 d .
H4 H 0.6576 0.1978 -0.1826 0.040 Uiso 1 1 calc R
C26 C 0.9180(2) 0.05730(11) 0.1114(2) 0.0304(6) Uani 1 1 d .
H26 H 0.9491 0.0781 0.0407 0.036 Uiso 1 1 calc R
C16 C 0.4120(2) 0.09481(10) 0.0224(2) 0.0280(6) Uani 1 1 d .
H16 H 0.4210 0.0615 -0.0296 0.034 Uiso 1 1 calc R
C6 C 0.5502(3) 0.10501(11) -0.4611(3) 0.0334(6) Uani 1 1 d .
H6 H 0.5196 0.1015 -0.5705 0.040 Uiso 1 1 calc R
C15 C 0.2772(3) 0.10420(11) 0.0511(3) 0.0349(7) Uani 1 1 d .
H15 H 0.1951 0.0772 0.0198 0.042 Uiso 1 1 calc R
C12 C 0.5176(3) 0.18199(11) 0.1420(2) 0.0316(6) Uani 1 1 d .
H12 H 0.5997 0.2091 0.1735 0.038 Uiso 1 1 calc R
C22 C 0.7379(3) 0.04056(10) 0.2354(2) 0.0281(6) Uani 1 1 d .
H22 H 0.6450 0.0499 0.2521 0.034 Uiso 1 1 calc R
C14 C 0.2610(3) 0.15269(12) 0.1250(3) 0.0382(7) Uani 1 1 d .
H14 H 0.1681 0.1591 0.1445 0.046 Uiso 1 1 calc R
C13 C 0.3814(3) 0.19169(12) 0.1702(3) 0.0385(7) Uani 1 1 d .
H13 H 0.3711 0.2252 0.2206 0.046 Uiso 1 1 calc R
C5 C 0.5878(3) 0.15659(11) -0.3898(3) 0.0388(7) Uani 1 1 d .
H5 H 0.5829 0.1890 -0.4508 0.047 Uiso 1 1 calc R
C23 C 0.8309(3) -0.00358(11) 0.3169(3) 0.0351(6) Uani 1 1 d .
H23 H 0.8000 -0.0246 0.3871 0.042 Uiso 1 1 calc R
C24 C 0.9680(3) -0.01728(11) 0.2971(3) 0.0377(7) Uani 1 1 d .
H24 H 1.0317 -0.0476 0.3532 0.045 Uiso 1 1 calc R
C25 C 1.0116(3) 0.01380(11) 0.1941(3) 0.0362(7) Uani 1 1 d .
H25 H 1.1064 0.0051 0.1805 0.043 Uiso 1 1 calc R
N1G N 0.9614(2) 0.17477(9) 0.4041(2) 0.0365(5) Uani 1 1 d .
C4G C 1.1577(3) 0.18472(11) 0.7146(3) 0.0376(7) Uani 1 1 d .
H4G H 1.2251 0.1881 0.8213 0.045 Uiso 1 1 calc R
C6G C 1.0971(3) 0.14645(11) 0.4660(3) 0.0389(7) Uani 1 1 d .
H6G H 1.1255 0.1221 0.4003 0.047 Uiso 1 1 calc R
C3G C 1.0204(3) 0.21385(12) 0.6558(3) 0.0499(8) Uani 1 1 d .
H3G H 0.9897 0.2379 0.7206 0.060 Uiso 1 1 calc R
C5G C 1.1969(3) 0.15069(11) 0.6185(3) 0.0401(7) Uani 1 1 d .
H5G H 1.2926 0.1300 0.6567 0.048 Uiso 1 1 calc R
C2G C 0.9273(3) 0.20794(13) 0.5014(3) 0.0486(8) Uani 1 1 d .
H2G H 0.8321 0.2289 0.4613 0.058 Uiso 1 1 calc R
H1O H 0.853(3) 0.1688(11) 0.214(3) 0.073(9) Uiso 1 1 d .
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
_geom_angle_site_symmetry_1
C6 C1 C2 120.5(2) .
C6 C1 N1 124.89(19) .
C2 C1 N1 114.6(2) .
O1 C7 C21 108.23(16) .
O1 C7 C3 105.82(17) .
C21 C7 C3 111.52(18) .
O1 C7 C11 109.80(18) .
C21 C7 C11 112.66(18) .
C3 C7 C11 108.59(16) .
N1 N1 C1 114.5(2) 3_654
C22 C21 C26 118.1(2) .
C22 C21 C7 124.39(19) .
C26 C21 C7 117.4(2) .
C4 C3 C2 118.0(2) .
C4 C3 C7 120.3(2) .
C2 C3 C7 121.7(2) .
C1 C2 C3 121.1(2) .
C12 C11 C16 118.3(2) .
C12 C11 C7 121.2(2) .
C16 C11 C7 120.5(2) .
C3 C4 C5 121.0(2) .
C25 C26 C21 121.1(2) .
C15 C16 C11 120.8(2) .
C5 C6 C1 118.6(2) .
C16 C15 C14 120.5(2) .
C11 C12 C13 120.9(2) .
C23 C22 C21 120.7(2) .
C13 C14 C15 119.3(2) .
C14 C13 C12 120.2(2) .
C6 C5 C4 120.8(2) .
C24 C23 C22 120.7(2) .
C23 C24 C25 119.0(2) .
C26 C25 C24 120.4(2) .
C2G N1G C6G 115.6(2) .
C5G C4G C3G 118.8(2) .
N1G C6G C5G 123.5(2) .
C4G C3G C2G 118.7(3) .
C4G C5G C6G 119.2(2) .
N1G C2G C3G 124.1(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.436(3) .
C1 C6 1.387(3) .
C1 C2 1.389(3) .
C1 N1 1.433(3) .
C7 C21 1.536(3) .
C7 C3 1.537(3) .
C7 C11 1.544(3) .
N1 N1 1.258(3) 3_654
C21 C22 1.390(3) .
C21 C26 1.392(3) .
C3 C4 1.384(3) .
C3 C2 1.390(3) .
C11 C12 1.382(3) .
C11 C16 1.395(3) .
C4 C5 1.392(3) .
C26 C25 1.379(3) .
C16 C15 1.380(3) .
C6 C5 1.379(3) .
C15 C14 1.384(3) .
C12 C13 1.393(3) .
C22 C23 1.385(3) .
C14 C13 1.382(3) .
C23 C24 1.380(3) .
C24 C25 1.386(3) .
N1G C2G 1.327(3) .
N1G C6G 1.338(3) .
C4G C5G 1.355(3) .
C4G C3G 1.358(3) .
C6G C5G 1.365(3) .
C3G C2G 1.367(3) .
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
_geom_torsion_site_symmetry_4
C6 C1 N1 N1 -2.4(3) 3_654
C2 C1 N1 N1 178.5(2) 3_654
O1 C7 C21 C22 117.4(2) .
C3 C7 C21 C22 -126.6(2) .
C11 C7 C21 C22 -4.2(3) .
O1 C7 C21 C26 -58.4(2) .
C3 C7 C21 C26 57.6(2) .
C11 C7 C21 C26 -179.98(19) .
O1 C7 C3 C4 -30.3(3) .
C21 C7 C3 C4 -147.8(2) .
C11 C7 C3 C4 87.5(2) .
O1 C7 C3 C2 152.07(19) .
C21 C7 C3 C2 34.6(3) .
C11 C7 C3 C2 -90.1(2) .
C6 C1 C2 C3 1.0(3) .
N1 C1 C2 C3 -179.91(18) .
C4 C3 C2 C1 -0.4(3) .
C7 C3 C2 C1 177.24(18) .
O1 C7 C11 C12 -5.4(3) .
C21 C7 C11 C12 115.3(2) .
C3 C7 C11 C12 -120.7(2) .
O1 C7 C11 C16 174.72(18) .
C21 C7 C11 C16 -64.6(2) .
C3 C7 C11 C16 59.5(3) .
C2 C3 C4 C5 -0.3(3) .
C7 C3 C4 C5 -178.0(2) .
C22 C21 C26 C25 0.8(3) .
C7 C21 C26 C25 176.9(2) .
C12 C11 C16 C15 -1.0(3) .
C7 C11 C16 C15 178.8(2) .
C2 C1 C6 C5 -0.8(3) .
N1 C1 C6 C5 -179.8(2) .
C11 C16 C15 C14 0.8(3) .
C16 C11 C12 C13 0.6(3) .
C7 C11 C12 C13 -179.2(2) .
C26 C21 C22 C23 -1.7(3) .
C7 C21 C22 C23 -177.5(2) .
C16 C15 C14 C13 -0.1(4) .
C15 C14 C13 C12 -0.3(4) .
C11 C12 C13 C14 0.0(3) .
C1 C6 C5 C4 0.1(4) .
C3 C4 C5 C6 0.4(4) .
C21 C22 C23 C24 1.3(3) .
C22 C23 C24 C25 -0.1(4) .
C21 C26 C25 C24 0.4(4) .
C23 C24 C25 C26 -0.8(4) .
C2G N1G C6G C5G -0.4(4) .
C5G C4G C3G C2G -0.3(4) .
C3G C4G C5G C6G -0.4(4) .
N1G C6G C5G C4G 0.8(4) .
C6G N1G C2G C3G -0.4(4) .
C4G C3G C2G N1G 0.8(5) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145372
