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#$Date: 2025-08-21 23:04:39 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301851 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/09/7050919.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_7050919
loop_
_publ_author_name
'Scott, Janet'
'Asami, Masaya'
'Tanaka, Koichi'
_publ_section_title
;
 Novel chromogenic, guest-sensitive host compounds
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1822
_journal_paper_doi               10.1039/b204221e
_journal_volume                  26
_journal_year                    2002
_chemical_formula_sum            'C48 H44 N4 O4'
_chemical_formula_weight         740.87
_chemical_name_systematic
; 
3-{4-[4-(3-hydroxy-3,3-diphenyl-prop-1-ynyl)-phenylazo]-phenyl}-1,
1-diphenyl-prop-2-yn-1-ol dimethylformamide solvate
;
_space_group_IT_number           2
_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                70.9510(10)
_cell_angle_beta                 70.7580(10)
_cell_angle_gamma                70.1610(10)
_cell_formula_units_Z            1
_cell_length_a                   9.7114(2)
_cell_length_b                   10.4231(2)
_cell_length_c                   11.8636(3)
_cell_measurement_temperature    294(2)
_cell_volume                     1034.91(4)
_computing_cell_refinement       'Nonius Collect'
_computing_data_collection       'Nonius Collect'
_computing_data_reduction        'Nonius Collect'
_computing_molecular_graphics    XSeed
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_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    0.0717
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4924
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         3.84
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9775
_exptl_absorpt_correction_T_min  0.9629
_exptl_crystal_colour            'red/pale orange dichroic'
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.1320
_refine_ls_R_factor_gt           0.0524
_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)+(0.0812P)²+0.0000P] where P==(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1559
_reflns_number_gt                2365
_reflns_number_total             4924
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b204221e.txt
_cod_data_source_block           c:
_cod_database_code               7050919
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.83310(13) 0.40049(11) 0.14485(10) 0.0512(3) Uani 1 1 d . . .
N2 N 0.51954(15) 0.05626(13) 0.47946(12) 0.0505(4) Uani 1 1 d . . .
C1 C 0.45119(18) 0.14888(16) 0.55936(14) 0.0463(4) Uani 1 1 d . . .
C2 C 0.52370(19) 0.25283(16) 0.53863(14) 0.0486(4) Uani 1 1 d . . .
C6 C 0.3195(2) 0.14240(18) 0.65103(16) 0.0579(5) Uani 1 1 d . . .
H6 H 0.2713 0.0738 0.6635 0.069 Uiso 1 1 calc R . .
C10 C 0.97622(18) 0.15916(17) 0.21212(15) 0.0471(4) Uani 1 1 d . . .
C8 C 0.7608(2) 0.28231(17) 0.35427(16) 0.0527(5) Uani 1 1 d . . .
C20 C 0.99771(19) 0.36165(17) 0.26950(15) 0.0484(4) Uani 1 1 d . . .
C7 C 0.6555(2) 0.26598(16) 0.43899(16) 0.0523(5) Uani 1 1 d . . .
C9 C 0.88908(18) 0.30122(16) 0.24505(14) 0.0449(4) Uani 1 1 d . . .
C3 C 0.4635(2) 0.34449(18) 0.61684(16) 0.0603(5) Uani 1 1 d . . .
H3 H 0.5122 0.4116 0.6074 0.072 Uiso 1 1 calc R . .
C21 C 1.0800(2) 0.44388(17) 0.17451(16) 0.0556(5) Uani 1 1 d . . .
H21 H 1.0662 0.4668 0.0957 0.067 Uiso 1 1 calc R . .
N1G N 0.47372(17) 0.20179(17) 0.10908(16) 0.0674(5) Uani 1 1 d . . .
C4 C 0.3324(2) 0.33608(19) 0.70780(16) 0.0661(6) Uani 1 1 d . . .
H4 H 0.2930 0.3980 0.7588 0.079 Uiso 1 1 calc R . .
C11 C 1.0407(2) 0.1529(2) 0.09140(17) 0.0619(5) Uani 1 1 d . . .
H11 H 1.0288 0.2350 0.0293 0.074 Uiso 1 1 calc R . .
C5 C 0.2598(2) 0.23711(19) 0.72357(17) 0.0659(5) Uani 1 1 d . . .
H5 H 0.1698 0.2340 0.7835 0.079 Uiso 1 1 calc R . .
O1G O 0.64162(18) 0.32136(18) 0.08005(14) 0.0947(5) Uani 1 1 d . . .
C15 C 0.9957(2) 0.0366(2) 0.30059(19) 0.0785(6) Uani 1 1 d . . .
H15 H 0.9539 0.0377 0.3831 0.094 Uiso 1 1 calc R . .
C1G C 0.5667(2) 0.2386(2) 0.1449(2) 0.0682(5) Uani 1 1 d . . .
H1G H 0.5758 0.1987 0.2254 0.082 Uiso 1 1 calc R . .
C22 C 1.1825(2) 0.4928(2) 0.1945(2) 0.0752(6) Uani 1 1 d . . .
H22 H 1.2374 0.5483 0.1291 0.090 Uiso 1 1 calc R . .
C13 C 1.1403(2) -0.0944(2) 0.1493(2) 0.0765(6) Uani 1 1 d . . .
H13 H 1.1944 -0.1794 0.1283 0.092 Uiso 1 1 calc R . .
C12 C 1.1230(3) 0.0266(2) 0.0609(2) 0.0753(6) Uani 1 1 d . . .
H12 H 1.1669 0.0248 -0.0212 0.090 Uiso 1 1 calc R . .
C25 C 1.0196(3) 0.3307(3) 0.38545(19) 0.0808(6) Uani 1 1 d . . .
H25 H 0.9641 0.2761 0.4513 0.097 Uiso 1 1 calc R . .
C23 C 1.2044(3) 0.4605(3) 0.3091(3) 0.0908(8) Uani 1 1 d . . .
H23 H 1.2744 0.4933 0.3222 0.109 Uiso 1 1 calc R . .
C14 C 1.0779(3) -0.0904(2) 0.2686(2) 0.0965(8) Uani 1 1 d . . .
H14 H 1.0899 -0.1732 0.3299 0.116 Uiso 1 1 calc R . .
C3G C 0.4483(3) 0.2650(3) -0.0130(2) 0.0971(8) Uani 1 1 d . . .
H3G1 H 0.4806 0.3502 -0.0470 0.146 Uiso 1 1 calc R . .
H3G2 H 0.3426 0.2860 -0.0083 0.146 Uiso 1 1 calc R . .
H3G3 H 0.5047 0.2008 -0.0647 0.146 Uiso 1 1 calc R . .
C2G C 0.3894(3) 0.1024(3) 0.1927(3) 0.1031(8) Uani 1 1 d . . .
H2G1 H 0.4077 0.0783 0.2727 0.155 Uiso 1 1 calc R . .
H2G2 H 0.4211 0.0192 0.1628 0.155 Uiso 1 1 calc R . .
H2G3 H 0.2835 0.1439 0.1980 0.155 Uiso 1 1 calc R . .
C24 C 1.1227(3) 0.3798(3) 0.4047(2) 0.1019(8) Uani 1 1 d . . .
H24 H 1.1369 0.3577 0.4833 0.122 Uiso 1 1 calc R . .
H1O H 0.761(3) 0.368(2) 0.1255(19) 0.097(7) 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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N2 C1 113.65(15) 2_656 . ?
C6 C1 C2 120.43(14) . . ?
C6 C1 N2 123.82(14) . . ?
C2 C1 N2 115.73(13) . . ?
C3 C2 C1 118.09(14) . . ?
C3 C2 C7 120.92(14) . . ?
C1 C2 C7 120.99(13) . . ?
C5 C6 C1 120.18(16) . . ?
C15 C10 C11 117.81(17) . . ?
C15 C10 C9 121.71(15) . . ?
C11 C10 C9 120.46(15) . . ?
C7 C8 C9 177.45(17) . . ?
C21 C20 C25 118.29(16) . . ?
C21 C20 C9 120.39(15) . . ?
C25 C20 C9 121.28(15) . . ?
C8 C7 C2 177.1(2) . . ?
O1 C9 C8 109.31(14) . . ?
O1 C9 C20 106.58(12) . . ?
C8 C9 C20 111.05(12) . . ?
O1 C9 C10 110.78(12) . . ?
C8 C9 C10 109.90(12) . . ?
C20 C9 C10 109.18(13) . . ?
C4 C3 C2 120.52(16) . . ?
C22 C21 C20 120.80(18) . . ?
C1G N1G C3G 120.59(19) . . ?
C1G N1G C2G 120.85(19) . . ?
C3G N1G C2G 118.49(18) . . ?
C5 C4 C3 120.49(15) . . ?
C10 C11 C12 120.99(19) . . ?
C4 C5 C6 120.18(17) . . ?
C10 C15 C14 120.65(19) . . ?
O1G C1G N1G 124.8(2) . . ?
C23 C22 C21 120.5(2) . . ?
C12 C13 C14 119.23(19) . . ?
C13 C12 C11 120.7(2) . . ?
C24 C25 C20 120.6(2) . . ?
C22 C23 C24 119.43(19) . . ?
C13 C14 C15 120.6(2) . . ?
C23 C24 C25 120.4(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.421(2) . ?
N2 N2 1.251(2) 2_656 ?
N2 C1 1.4209(19) . ?
C1 C6 1.385(2) . ?
C1 C2 1.400(2) . ?
C2 C3 1.399(2) . ?
C2 C7 1.439(2) . ?
C6 C5 1.374(2) . ?
C10 C15 1.364(3) . ?
C10 C11 1.375(2) . ?
C10 C9 1.540(2) . ?
C8 C7 1.189(2) . ?
C8 C9 1.485(2) . ?
C20 C21 1.373(2) . ?
C20 C25 1.378(2) . ?
C20 C9 1.538(2) . ?
C3 C4 1.379(2) . ?
C21 C22 1.373(2) . ?
N1G C1G 1.318(2) . ?
N1G C3G 1.448(3) . ?
N1G C2G 1.448(3) . ?
C4 C5 1.370(2) . ?
C11 C12 1.381(2) . ?
O1G C1G 1.220(2) . ?
C15 C14 1.395(3) . ?
C22 C23 1.361(3) . ?
C13 C12 1.352(3) . ?
C13 C14 1.352(3) . ?
C25 C24 1.376(3) . ?
C23 C24 1.364(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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N2 C1 C6 -20.9(3) 2_656 . . . ?
N2 N2 C1 C2 160.55(19) 2_656 . . . ?
C6 C1 C2 C3 3.1(3) . . . . ?
N2 C1 C2 C3 -178.29(16) . . . . ?
C6 C1 C2 C7 -176.25(17) . . . . ?
N2 C1 C2 C7 2.3(2) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
N2 C1 C6 C5 -179.27(17) . . . . ?
C9 C8 C7 C2 -73(6) . . . . ?
C3 C2 C7 C8 -67(3) . . . . ?
C1 C2 C7 C8 112(3) . . . . ?
C7 C8 C9 O1 54(4) . . . . ?
C7 C8 C9 C20 172(4) . . . . ?
C7 C8 C9 C10 -67(4) . . . . ?
C21 C20 C9 O1 -31.7(2) . . . . ?
C25 C20 C9 O1 150.82(17) . . . . ?
C21 C20 C9 C8 -150.71(16) . . . . ?
C25 C20 C9 C8 31.9(2) . . . . ?
C21 C20 C9 C10 87.95(18) . . . . ?
C25 C20 C9 C10 -89.5(2) . . . . ?
C15 C10 C9 O1 -157.11(16) . . . . ?
C11 C10 C9 O1 24.7(2) . . . . ?
C15 C10 C9 C8 -36.2(2) . . . . ?
C11 C10 C9 C8 145.59(16) . . . . ?
C15 C10 C9 C20 85.8(2) . . . . ?
C11 C10 C9 C20 -92.38(18) . . . . ?
C1 C2 C3 C4 -3.0(3) . . . . ?
C7 C2 C3 C4 176.41(18) . . . . ?
C25 C20 C21 C22 0.6(3) . . . . ?
C9 C20 C21 C22 -176.89(16) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C15 C10 C11 C12 -0.2(3) . . . . ?
C9 C10 C11 C12 178.06(16) . . . . ?
C3 C4 C5 C6 1.9(3) . . . . ?
C1 C6 C5 C4 -1.8(3) . . . . ?
C11 C10 C15 C14 -0.4(3) . . . . ?
C9 C10 C15 C14 -178.62(19) . . . . ?
C3G N1G C1G O1G -3.1(3) . . . . ?
C2G N1G C1G O1G 179.9(2) . . . . ?
C20 C21 C22 C23 0.0(3) . . . . ?
C14 C13 C12 C11 -1.0(3) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C21 C20 C25 C24 -0.8(3) . . . . ?
C9 C20 C25 C24 176.7(2) . . . . ?
C21 C22 C23 C24 -0.4(4) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C10 C15 C14 C13 0.3(4) . . . . ?
C22 C23 C24 C25 0.3(4) . . . . ?
C20 C25 C24 C23 0.3(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139175309
