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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/4/50/39/4503952.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.
#
data_4503952
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            'C21 H19 N O2'
_chemical_formula_weight         317.37
_chemical_name_systematic
; 
 (E)-(3,3'-(diazene-1,2-diyl)bis(3,1-phenylene))bis(diphenylmethanol) dioxane solvate 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.171(2)
_cell_angle_beta                 98.851(2)
_cell_angle_gamma                105.778(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9540(4)
_cell_length_b                   9.0428(4)
_cell_length_c                   10.9379(6)
_cell_measurement_temperature    123(2)
_cell_volume                     811.84(7)
_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 0.970
_diffrn_measured_fraction_theta_max 0.970
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1246
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3858
_diffrn_reflns_theta_full        28.17
_diffrn_reflns_theta_max         28.17
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.672
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1637
_refine_ls_R_factor_gt           0.0589
_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)+(0.0720P)²+0.0311P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1606
_reflns_number_gt                1909
_reflns_number_total             3858
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060522bsi20060803_014632.cif
_cod_data_source_block           2.dioxane
_cod_original_sg_symbol_H-M      P(-1)
_cod_database_code               4503952
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.26196(19) 0.3343(2) 0.55982(15) 0.0253(4) Uani 1 1 d .
N1 N 0.5135(2) 0.9365(2) 0.9780(2) 0.0261(5) Uani 1 1 d .
C3 C 0.2979(3) 0.5548(3) 0.7367(2) 0.0193(5) Uani 1 1 d .
C11 C 0.1960(3) 0.2801(3) 0.7581(2) 0.0196(5) Uani 1 1 d .
C16 C 0.2063(3) 0.3193(3) 0.8894(2) 0.0238(6) Uani 1 1 d .
H16 H 0.2886 0.4107 0.9432 0.029 Uiso 1 1 calc R
C21 C 0.4855(3) 0.3902(3) 0.7351(2) 0.0194(5) Uani 1 1 d .
C1 C 0.3884(3) 0.8234(3) 0.8755(2) 0.0209(6) Uani 1 1 d .
C7 C 0.3122(3) 0.3867(3) 0.6972(2) 0.0203(6) Uani 1 1 d .
C2 C 0.4083(3) 0.6751(3) 0.8357(2) 0.0210(6) Uani 1 1 d .
H2 H 0.4995 0.6556 0.8773 0.025 Uiso 1 1 calc R
C6 C 0.2567(3) 0.8556(3) 0.8156(2) 0.0235(6) Uani 1 1 d .
H6 H 0.2420 0.9566 0.8427 0.028 Uiso 1 1 calc R
C12 C 0.0736(3) 0.1467(3) 0.6809(2) 0.0240(6) Uani 1 1 d .
H12 H 0.0643 0.1178 0.5907 0.029 Uiso 1 1 calc R
C22 C 0.5391(3) 0.3114(3) 0.8196(2) 0.0228(6) Uani 1 1 d .
H22 H 0.4663 0.2512 0.8593 0.027 Uiso 1 1 calc R
C4 C 0.1676(3) 0.5876(3) 0.6761(2) 0.0235(6) Uani 1 1 d .
H4 H 0.0913 0.5077 0.6070 0.028 Uiso 1 1 calc R
C25 C 0.7528(3) 0.4812(3) 0.7026(2) 0.0282(6) Uani 1 1 d .
H25 H 0.8254 0.5384 0.6611 0.034 Uiso 1 1 calc R
C14 C -0.0225(3) 0.0948(3) 0.8663(3) 0.0287(6) Uani 1 1 d .
H14 H -0.0965 0.0314 0.9031 0.034 Uiso 1 1 calc R
C5 C 0.1471(3) 0.7363(3) 0.7151(2) 0.0264(6) Uani 1 1 d .
H5 H 0.0569 0.7563 0.6724 0.032 Uiso 1 1 calc R
C26 C 0.5947(3) 0.4751(3) 0.6765(2) 0.0249(6) Uani 1 1 d .
H26 H 0.5601 0.5294 0.6180 0.030 Uiso 1 1 calc R
C15 C 0.0982(3) 0.2269(3) 0.9437(3) 0.0290(6) Uani 1 1 d .
H15 H 0.1076 0.2547 1.0339 0.035 Uiso 1 1 calc R
C13 C -0.0358(3) 0.0549(3) 0.7357(3) 0.0281(6) Uani 1 1 d .
H13 H -0.1197 -0.0354 0.6825 0.034 Uiso 1 1 calc R
C23 C 0.6988(3) 0.3196(3) 0.8471(2) 0.0270(6) Uani 1 1 d .
H23 H 0.7343 0.2663 0.9062 0.032 Uiso 1 1 calc R
C24 C 0.8056(3) 0.4044(3) 0.7890(2) 0.0293(6) Uani 1 1 d .
H24 H 0.9145 0.4100 0.8081 0.035 Uiso 1 1 calc R
O1G O 0.39526(18) 0.0907(2) 0.48678(15) 0.0278(4) Uani 1 1 d .
C3G C 0.4871(3) -0.0919(3) 0.5878(2) 0.0288(6) Uani 1 1 d .
H3G1 H 0.5341 -0.0101 0.6709 0.035 Uiso 1 1 calc R
H3G2 H 0.4512 -0.1973 0.6057 0.035 Uiso 1 1 calc R
C2G C 0.3467(3) -0.0586(3) 0.5175(3) 0.0320(7) Uani 1 1 d .
H2G1 H 0.2949 -0.1449 0.4375 0.038 Uiso 1 1 calc R
H2G2 H 0.2678 -0.0569 0.5716 0.038 Uiso 1 1 calc R
H1O H 0.312(4) 0.256(4) 0.530(3) 0.084(12) 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
N1 N1 C1 114.4(2) 2_677
C4 C3 C2 118.0(2) .
C4 C3 C7 119.8(2) .
C2 C3 C7 122.2(2) .
C16 C11 C12 118.6(2) .
C16 C11 C7 121.0(2) .
C12 C11 C7 120.3(2) .
C11 C16 C15 121.1(2) .
C22 C21 C26 118.3(2) .
C22 C21 C7 124.7(2) .
C26 C21 C7 117.0(2) .
C2 C1 C6 120.5(2) .
C2 C1 N1 115.1(2) .
C6 C1 N1 124.4(2) .
O1 C7 C21 108.37(18) .
O1 C7 C3 106.27(19) .
C21 C7 C3 110.98(18) .
O1 C7 C11 110.06(18) .
C21 C7 C11 113.96(19) .
C3 C7 C11 106.94(18) .
C3 C2 C1 121.5(2) .
C5 C6 C1 118.3(2) .
C11 C12 C13 120.1(2) .
C21 C22 C23 120.6(2) .
C3 C4 C5 120.9(2) .
C26 C25 C24 120.2(2) .
C13 C14 C15 119.9(2) .
C6 C5 C4 120.9(2) .
C25 C26 C21 120.9(2) .
C14 C15 C16 119.9(2) .
C14 C13 C12 120.4(2) .
C24 C23 C22 120.5(2) .
C23 C24 C25 119.4(2) .
C3G O1G C2G 110.14(18) 2_656
O1G C3G C2G 110.6(2) 2_656
O1G C2G C3G 111.0(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.435(3) .
N1 N1 1.251(4) 2_677
N1 C1 1.437(3) .
C3 C4 1.387(3) .
C3 C2 1.387(3) .
C3 C7 1.535(3) .
C11 C16 1.387(3) .
C11 C12 1.392(3) .
C11 C7 1.548(3) .
C16 C15 1.390(3) .
C21 C22 1.386(3) .
C21 C26 1.396(3) .
C21 C7 1.534(3) .
C1 C2 1.388(3) .
C1 C6 1.391(3) .
C6 C5 1.388(3) .
C12 C13 1.399(3) .
C22 C23 1.393(3) .
C4 C5 1.392(3) .
C25 C26 1.384(3) .
C25 C24 1.385(3) .
C14 C13 1.375(4) .
C14 C15 1.380(3) .
C23 C24 1.378(3) .
O1G C3G 1.427(3) 2_656
O1G C2G 1.429(3) .
C3G O1G 1.427(3) 2_656
C3G C2G 1.507(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_1
C12 C11 C16 C15 0.7(4) .
C7 C11 C16 C15 177.5(2) .
N1 N1 C1 C2 -172.9(3) 2_677
N1 N1 C1 C6 8.5(4) 2_677
C22 C21 C7 O1 -125.2(2) .
C26 C21 C7 O1 52.7(3) .
C22 C21 C7 C3 118.5(2) .
C26 C21 C7 C3 -63.6(3) .
C22 C21 C7 C11 -2.3(3) .
C26 C21 C7 C11 175.6(2) .
C4 C3 C7 O1 40.9(3) .
C2 C3 C7 O1 -142.0(2) .
C4 C3 C7 C21 158.5(2) .
C2 C3 C7 C21 -24.4(3) .
C4 C3 C7 C11 -76.7(3) .
C2 C3 C7 C11 100.5(2) .
C16 C11 C7 O1 -171.2(2) .
C12 C11 C7 O1 5.5(3) .
C16 C11 C7 C21 66.8(3) .
C12 C11 C7 C21 -116.5(2) .
C16 C11 C7 C3 -56.2(3) .
C12 C11 C7 C3 120.5(2) .
C4 C3 C2 C1 1.3(3) .
C7 C3 C2 C1 -175.9(2) .
C6 C1 C2 C3 -0.6(3) .
N1 C1 C2 C3 -179.2(2) .
C2 C1 C6 C5 -0.4(3) .
N1 C1 C6 C5 178.1(2) .
C16 C11 C12 C13 -0.1(3) .
C7 C11 C12 C13 -176.9(2) .
C26 C21 C22 C23 1.2(3) .
C7 C21 C22 C23 179.1(2) .
C2 C3 C4 C5 -1.0(3) .
C7 C3 C4 C5 176.3(2) .
C1 C6 C5 C4 0.6(3) .
C3 C4 C5 C6 0.1(4) .
C24 C25 C26 C21 -0.8(4) .
C22 C21 C26 C25 -0.3(3) .
C7 C21 C26 C25 -178.4(2) .
C13 C14 C15 C16 0.0(4) .
C11 C16 C15 C14 -0.7(4) .
C15 C14 C13 C12 0.7(4) .
C11 C12 C13 C14 -0.6(4) .
C21 C22 C23 C24 -1.0(4) .
C22 C23 C24 C25 -0.2(4) .
C26 C25 C24 C23 1.1(4) .
C3G O1G C2G C3G 57.2(3) 2_656
O1G C3G C2G O1G -57.5(3) 2_656
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145373
