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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/4/50/73/4507390.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_4507390
loop_
_publ_author_name
'Sreevidya, Thekku Veedu'
'Cao, Deng-Ke'
'Lavy, Tali'
'Botoshansky, Mark'
'Kaftory, Menahem'
_publ_section_title
;
 Unexpected Molecular Flip in Solid-State Photodimerization
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              936
_journal_paper_doi               10.1021/cg3016707
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C30 H22 O2, 2(C5 H5 N O)'
_chemical_formula_sum            'C40 H32 N2 O4'
_chemical_formula_weight         604.68
_chemical_name_systematic
; 
 1,1,6,6-Tetraphenyl-2,4-hexadiyne-1,6-diol : 2(2(1H)-pyridone) 
;
_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                85.12(2)
_cell_angle_beta                 75.70(2)
_cell_angle_gamma                81.12(2)
_cell_formula_units_Z            1
_cell_length_a                   7.795(2)
_cell_length_b                   8.071(2)
_cell_length_c                   13.457(3)
_cell_measurement_reflns_used    6417
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.32
_cell_measurement_theta_min      2.06
_cell_volume                     809.6(4)
_computing_cell_refinement       'DENZO HKL2000 (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius, 2006)'
_computing_data_reduction        'DENZO HKL2000 (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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  0.045
_diffrn_reflns_av_sigmaI/netI    0.0556
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6417
_diffrn_reflns_theta_full        24.67
_diffrn_reflns_theta_max         24.67
_diffrn_reflns_theta_min         1.56
_diffrn_standards_decay_%        none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             318
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2727
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0458
_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)+(0.0624P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1225
_reflns_number_gt                1802
_reflns_number_total             2727
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3016707_si_004.cif
_cod_data_source_block           I-c_dark
_cod_original_cell_volume        809.6(3)
_cod_database_code               4507390
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 0.35407(15) 1.08115(15) 0.23560(9) 0.0449(3) Uani 1 1 d .
H1 H 0.4216 1.0313 0.2697 0.054 Uiso 1 1 calc R
C1 C 0.0394(2) 0.9980(2) 0.44778(13) 0.0449(5) Uani 1 1 d .
C2 C 0.1068(2) 0.9953(2) 0.35823(13) 0.0438(5) Uani 1 1 d .
C3 C 0.2032(2) 0.9953(2) 0.24839(12) 0.0369(4) Uani 1 1 d .
C4 C 0.0854(2) 1.0886(2) 0.18004(13) 0.0380(4) Uani 1 1 d .
C5 C -0.0984(2) 1.1138(3) 0.21170(16) 0.0564(6) Uani 1 1 d .
H5 H -0.1540 1.0794 0.2780 0.068 Uiso 1 1 calc R
C6 C -0.2013(3) 1.1903(3) 0.14540(19) 0.0731(7) Uani 1 1 d .
H6 H -0.3252 1.2061 0.1675 0.088 Uiso 1 1 calc R
C7 C -0.1220(3) 1.2424(3) 0.04827(18) 0.0679(6) Uani 1 1 d .
H7 H -0.1914 1.2945 0.0044 0.082 Uiso 1 1 calc R
C8 C 0.0611(3) 1.2175(3) 0.01543(16) 0.0636(6) Uani 1 1 d .
H8 H 0.1159 1.2523 -0.0510 0.076 Uiso 1 1 calc R
C9 C 0.1638(2) 1.1409(3) 0.08096(14) 0.0502(5) Uani 1 1 d .
H9 H 0.2877 1.1243 0.0581 0.060 Uiso 1 1 calc R
C10 C 0.2604(2) 0.8143(2) 0.21458(12) 0.0370(4) Uani 1 1 d .
C11 C 0.4294(2) 0.7658(3) 0.15379(14) 0.0489(5) Uani 1 1 d .
H11 H 0.5100 0.8432 0.1344 0.059 Uiso 1 1 calc R
C12 C 0.4793(3) 0.6035(3) 0.12169(15) 0.0590(6) Uani 1 1 d .
H12 H 0.5939 0.5717 0.0820 0.071 Uiso 1 1 calc R
C13 C 0.3606(3) 0.4894(3) 0.14817(16) 0.0603(6) Uani 1 1 d .
H13 H 0.3946 0.3804 0.1263 0.072 Uiso 1 1 calc R
C14 C 0.1914(3) 0.5357(3) 0.20702(16) 0.0617(6) Uani 1 1 d .
H14 H 0.1104 0.4585 0.2246 0.074 Uiso 1 1 calc R
C15 C 0.1421(3) 0.6977(2) 0.23999(15) 0.0509(5) Uani 1 1 d .
H15 H 0.0275 0.7287 0.2799 0.061 Uiso 1 1 calc R
O2 O 0.4607(2) 0.0686(2) 0.62512(11) 0.0745(5) Uani 1 1 d .
N1A N 0.3802(2) 0.2162(2) 0.48970(13) 0.0644(5) Uani 1 1 d .
H1NA H 0.4192 0.1281 0.4547 0.077 Uiso 1 1 calc R
C16A C 0.3945(3) 0.2066(3) 0.58837(17) 0.0587(6) Uani 1 1 d .
C17A C 0.3291(3) 0.3555(4) 0.64156(19) 0.0748(7) Uani 1 1 d .
H17A H 0.3350 0.3574 0.7096 0.090 Uiso 1 1 calc R
C18 C 0.2578(3) 0.4957(3) 0.5950(2) 0.0822(8) Uani 1 1 d .
H18A H 0.2163 0.5927 0.6313 0.099 Uiso 1 1 calc R
C19 C 0.2462(3) 0.4960(4) 0.4932(2) 0.0828(8) Uani 1 1 d .
H19A H 0.1962 0.5917 0.4614 0.099 Uiso 1 1 calc R
C20A C 0.3086(3) 0.3555(3) 0.4424(2) 0.0814(8) Uani 1 1 d .
H20A H 0.3028 0.3533 0.3743 0.098 Uiso 1 1 calc R
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_3
C3 O1 H1 109.5 .
C2 C1 C1 179.7(3) 2_576
C1 C2 C3 175.68(19) .
O1 C3 C2 108.49(14) .
O1 C3 C4 107.52(13) .
C2 C3 C4 111.38(14) .
O1 C3 C10 111.05(13) .
C2 C3 C10 109.89(14) .
C4 C3 C10 108.49(14) .
C5 C4 C9 118.33(17) .
C5 C4 C3 122.14(15) .
C9 C4 C3 119.42(15) .
C4 C5 C6 120.50(19) .
C4 C5 H5 119.7 .
C6 C5 H5 119.7 .
C7 C6 C5 120.48(19) .
C7 C6 H6 119.8 .
C5 C6 H6 119.8 .
C6 C7 C8 119.7(2) .
C6 C7 H7 120.1 .
C8 C7 H7 120.1 .
C7 C8 C9 119.99(19) .
C7 C8 H8 120.0 .
C9 C8 H8 120.0 .
C4 C9 C8 121.00(18) .
C4 C9 H9 119.5 .
C8 C9 H9 119.5 .
C15 C10 C11 118.38(17) .
C15 C10 C3 120.84(15) .
C11 C10 C3 120.72(16) .
C12 C11 C10 120.61(18) .
C12 C11 H11 119.7 .
C10 C11 H11 119.7 .
C13 C12 C11 120.17(18) .
C13 C12 H12 119.9 .
C11 C12 H12 119.9 .
C12 C13 C14 120.1(2) .
C12 C13 H13 119.9 .
C14 C13 H13 119.9 .
C13 C14 C15 119.6(2) .
C13 C14 H14 120.2 .
C15 C14 H14 120.2 .
C10 C15 C14 121.04(18) .
C10 C15 H15 119.5 .
C14 C15 H15 119.5 .
C16A N1A C20A 124.4(2) .
C16A N1A H1NA 117.8 .
C20A N1A H1NA 117.8 .
O2 C16A N1A 118.9(2) .
O2 C16A C17A 126.0(2) .
N1A C16A C17A 115.1(2) .
C18 C17A C16A 121.1(2) .
C18 C17A H17A 119.5 .
C16A C17A H17A 119.5 .
C17A C18 C19 120.7(3) .
C17A C18 H18A 119.7 .
C19 C18 H18A 119.7 .
C20A C19 C18 118.5(3) .
C20A C19 H19A 120.8 .
C18 C19 H19A 120.8 .
C19 C20A N1A 120.3(3) .
C19 C20A H20A 119.8 .
N1A C20A H20A 119.8 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.4229(19) .
O1 H1 0.8200 .
C1 C2 1.190(2) .
C1 C1 1.389(3) 2_576
C2 C3 1.483(2) .
C3 C4 1.530(2) .
C3 C10 1.534(2) .
C4 C5 1.378(2) .
C4 C9 1.382(2) .
C5 C6 1.388(3) .
C5 H5 0.9300 .
C6 C7 1.362(3) .
C6 H6 0.9300 .
C7 C8 1.374(3) .
C7 H7 0.9300 .
C8 C9 1.380(3) .
C8 H8 0.9300 .
C9 H9 0.9300 .
C10 C15 1.382(2) .
C10 C11 1.386(2) .
C11 C12 1.382(3) .
C11 H11 0.9300 .
C12 C13 1.370(3) .
C12 H12 0.9300 .
C13 C14 1.374(3) .
C13 H13 0.9300 .
C14 C15 1.383(3) .
C14 H14 0.9300 .
C15 H15 0.9300 .
O2 C16A 1.267(3) .
N1A C16A 1.354(3) .
N1A C20A 1.357(3) .
N1A H1NA 0.8600 .
C16A C17A 1.412(3) .
C17A C18 1.356(3) .
C17A H17A 0.9300 .
C18 C19 1.395(4) .
C18 H18A 0.9300 .
C19 C20A 1.336(4) .
C19 H19A 0.9300 .
C20A H20A 0.9300 .
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
C1 C1 C2 C3 72(54) 2_576
C1 C2 C3 O1 -16(3) .
C1 C2 C3 C4 -134(3) .
C1 C2 C3 C10 105(3) .
O1 C3 C4 C5 -140.00(17) .
C2 C3 C4 C5 -21.3(2) .
C10 C3 C4 C5 99.82(19) .
O1 C3 C4 C9 44.0(2) .
C2 C3 C4 C9 162.70(16) .
C10 C3 C4 C9 -76.2(2) .
C9 C4 C5 C6 -0.1(3) .
C3 C4 C5 C6 -176.2(2) .
C4 C5 C6 C7 -0.4(4) .
C5 C6 C7 C8 0.6(4) .
C6 C7 C8 C9 -0.4(4) .
C5 C4 C9 C8 0.4(3) .
C3 C4 C9 C8 176.58(18) .
C7 C8 C9 C4 -0.1(3) .
O1 C3 C10 C15 166.22(15) .
C2 C3 C10 C15 46.2(2) .
C4 C3 C10 C15 -75.82(19) .
O1 C3 C10 C11 -16.8(2) .
C2 C3 C10 C11 -136.82(16) .
C4 C3 C10 C11 101.18(17) .
C15 C10 C11 C12 -1.6(3) .
C3 C10 C11 C12 -178.66(16) .
C10 C11 C12 C13 1.2(3) .
C11 C12 C13 C14 -0.2(3) .
C12 C13 C14 C15 -0.5(3) .
C11 C10 C15 C14 0.9(3) .
C3 C10 C15 C14 178.02(17) .
C13 C14 C15 C10 0.1(3) .
C20A N1A C16A O2 178.6(2) .
C20A N1A C16A C17A -0.3(3) .
O2 C16A C17A C18 -178.8(2) .
N1A C16A C17A C18 0.1(3) .
C16A C17A C18 C19 0.5(4) .
C17A C18 C19 C20A -0.7(4) .
C18 C19 C20A N1A 0.4(4) .
C16A N1A C20A C19 0.1(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 13695472
