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#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/46/1504662.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_1504662
loop_
_publ_author_name
'Yumoto, Koji'
'Irie, Masahiro'
'Matsuda, Kenji'
_publ_contact_author
;Prof. Kenji. Matsuda
Department of Chemistry and Biochemistry
Graduate School of Engineering, Kyushu University
Motooka 744, Nishi-ku, Fukuoka 819-0395, Japan
;
_publ_section_title
;
 Control of the photoreactivity of diarylethene derivatives by
 quaternarization of the pyridylethynyl group.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2051
_journal_page_last               2054
_journal_paper_doi               10.1021/ol8005216
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C41 H26 F18 N2 P2 S2'
_chemical_formula_weight         1014.70
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.929(2)
_cell_length_b                   34.278(3)
_cell_length_c                   9.4606(9)
_cell_measurement_reflns_used    4244
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      21.22
_cell_measurement_theta_min      2.37
_cell_volume                     8408.5(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20381
_diffrn_reflns_theta_full        25.27
_diffrn_reflns_theta_max         25.27
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.318
_exptl_absorpt_correction_T_max  0.9689
_exptl_absorpt_correction_T_min  0.9248
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             4080
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.616
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         3818
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      2.616
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0555
_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)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0791
_reflns_number_gt                2944
_reflns_number_total             3818
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol8005216-file005.cif
_cod_data_source_block           2a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        8408.6(13)
_cod_original_sg_symbol_H-M      Fdd2
_cod_database_code               1504662
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
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
P1 P 0.23777(6) 0.07370(3) 0.34351(17) 0.0712(4) Uani 1 1 d .
S1 S 0.08392(4) 0.04908(3) 0.56014(12) 0.0569(3) Uani 1 1 d .
C2 C 0.04090(13) 0.03516(10) 0.7985(4) 0.0408(10) Uani 1 1 d .
C1 C 0.06152(14) 0.01599(11) 0.6833(4) 0.0467(11) Uani 1 1 d .
C3 C 0.04579(13) 0.07593(10) 0.7872(4) 0.0414(10) Uani 1 1 d .
H3 H 0.0351 0.0932 0.8601 0.050 Uiso 1 1 calc R
C5 C 0.01638(14) 0.01453(10) 0.9178(4) 0.0406(10) Uani 1 1 d .
C4 C 0.06700(14) 0.08868(11) 0.6638(4) 0.0454(11) Uani 1 1 d .
C9 C 0.07036(15) -0.05837(12) 0.6419(5) 0.0543(12) Uani 1 1 d .
C13 C 0.05150(15) -0.15876(12) 0.5057(5) 0.0570(12) Uani 1 1 d .
H13 H 0.0394 -0.1715 0.4230 0.068 Uiso 1 1 calc R
C10 C 0.07108(15) -0.10052(12) 0.6293(5) 0.0473(11) Uani 1 1 d .
C11 C 0.08677(17) -0.12293(13) 0.7405(5) 0.0626(13) Uani 1 1 d .
H11 H 0.0995 -0.1110 0.8241 0.075 Uiso 1 1 calc R
C8 C 0.06620(15) -0.02455(13) 0.6611(4) 0.0512(12) Uani 1 1 d .
C16 C 0.07482(14) 0.12912(11) 0.6140(5) 0.0475(11) Uani 1 1 d .
C19 C 0.08773(18) 0.20516(14) 0.5256(6) 0.0776(17) Uani 1 1 d .
H19 H 0.0914 0.2313 0.4939 0.093 Uiso 1 1 calc R
C12 C 0.08410(17) -0.16283(13) 0.7308(5) 0.0622(12) Uani 1 1 d .
H12 H 0.0955 -0.1783 0.8080 0.075 Uiso 1 1 calc R
C18 C 0.07256(16) 0.19792(13) 0.6611(5) 0.0585(12) Uani 1 1 d .
H18 H 0.0664 0.2190 0.7243 0.070 Uiso 1 1 calc R
C14 C 0.05370(15) -0.11873(11) 0.5082(5) 0.0547(12) Uani 1 1 d .
H14 H 0.0435 -0.1039 0.4282 0.066 Uiso 1 1 calc R
C17 C 0.06607(14) 0.15966(12) 0.7064(5) 0.0528(11) Uani 1 1 d .
H17 H 0.0556 0.1545 0.8009 0.063 Uiso 1 1 calc R
C21 C 0.09031(16) 0.13687(13) 0.4799(5) 0.0675(13) Uani 1 1 d .
H21 H 0.0962 0.1160 0.4157 0.081 Uiso 1 1 calc R
C15 C 0.06121(15) -0.22296(11) 0.6108(5) 0.0739(15) Uani 1 1 d .
H15A H 0.0953 -0.2345 0.5950 0.111 Uiso 1 1 calc R
H15B H 0.0381 -0.2303 0.5333 0.111 Uiso 1 1 calc R
H15C H 0.0471 -0.2325 0.7005 0.111 Uiso 1 1 calc R
C20 C 0.0976(2) 0.17524(15) 0.4361(6) 0.0919(18) Uani 1 1 d .
H20 H 0.1096 0.1805 0.3431 0.110 Uiso 1 1 calc R
N1 N 0.06597(12) -0.18017(9) 0.6164(4) 0.0525(10) Uani 1 1 d .
F6 F 0.23472(13) 0.04072(8) 0.4612(3) 0.1129(12) Uani 1 1 d .
F7 F 0.23692(12) 0.04201(7) 0.2231(3) 0.1022(10) Uani 1 1 d .
F9 F 0.23855(11) 0.10659(7) 0.2260(3) 0.0989(10) Uani 1 1 d .
F4 F 0.23831(18) 0.10521(8) 0.4616(3) 0.1528(16) Uani 1 1 d .
F8 F 0.29713(11) 0.07081(11) 0.3440(5) 0.1491(13) Uani 1 1 d .
F5 F 0.17670(11) 0.07511(10) 0.3374(4) 0.1423(13) Uani 1 1 d .
C6 C 0.0292(2) 0.02704(12) 1.0651(5) 0.0695(13) Uani 1 1 d .
C7 C 0.0000 0.0000 1.1633(8) 0.075(2) Uani 1 2 d S
F1 F 0.07950(13) 0.02282(11) 1.0921(3) 0.1529(17) Uani 1 1 d .
F2 F 0.0184(2) 0.06299(8) 1.0959(5) 0.216(3) Uani 1 1 d .
F3 F -0.03099(14) 0.01871(12) 1.2452(5) 0.195(2) Uani 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
F8 P1 F4 91.9(3) . .
F8 P1 F7 88.4(2) . .
F4 P1 F7 179.5(2) . .
F8 P1 F9 92.0(2) . .
F4 P1 F9 90.57(14) . .
F7 P1 F9 89.04(17) . .
F8 P1 F5 177.3(2) . .
F4 P1 F5 90.8(2) . .
F7 P1 F5 88.91(19) . .
F9 P1 F5 88.03(18) . .
F8 P1 F6 90.11(19) . .
F4 P1 F6 89.49(19) . .
F7 P1 F6 90.88(13) . .
F9 P1 F6 177.88(19) . .
F5 P1 F6 89.85(19) . .
C1 S1 C4 92.7(2) . .
C1 C2 C3 112.2(3) . .
C1 C2 C5 122.9(3) . .
C3 C2 C5 125.0(3) . .
C2 C1 C8 128.3(4) . .
C2 C1 S1 110.5(3) . .
C8 C1 S1 121.2(3) . .
C4 C3 C2 114.8(3) . .
C4 C3 H3 122.6 . .
C2 C3 H3 122.6 . .
C5 C5 C2 130.12(19) 2 .
C5 C5 C6 111.3(2) 2 .
C2 C5 C6 118.6(3) . .
C3 C4 C16 129.0(4) . .
C3 C4 S1 109.7(3) . .
C16 C4 S1 121.3(3) . .
C8 C9 C10 173.8(5) . .
N1 C13 C14 121.6(4) . .
N1 C13 H13 119.2 . .
C14 C13 H13 119.2 . .
C11 C10 C14 118.9(4) . .
C11 C10 C9 120.1(4) . .
C14 C10 C9 121.0(4) . .
C10 C11 C12 119.6(4) . .
C10 C11 H11 120.2 . .
C12 C11 H11 120.2 . .
C9 C8 C1 179.5(5) . .
C21 C16 C17 119.5(4) . .
C21 C16 C4 121.5(4) . .
C17 C16 C4 119.1(4) . .
C20 C19 C18 120.3(5) . .
C20 C19 H19 119.8 . .
C18 C19 H19 119.8 . .
N1 C12 C11 121.4(4) . .
N1 C12 H12 119.3 . .
C11 C12 H12 119.3 . .
C19 C18 C17 119.8(4) . .
C19 C18 H18 120.1 . .
C17 C18 H18 120.1 . .
C13 C14 C10 118.7(4) . .
C13 C14 H14 120.7 . .
C10 C14 H14 120.7 . .
C16 C17 C18 120.0(4) . .
C16 C17 H17 120.0 . .
C18 C17 H17 120.0 . .
C16 C21 C20 120.2(5) . .
C16 C21 H21 119.9 . .
C20 C21 H21 119.9 . .
N1 C15 H15A 109.5 . .
N1 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
N1 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C19 C20 C21 120.2(5) . .
C19 C20 H20 119.9 . .
C21 C20 H20 119.9 . .
C12 N1 C13 119.7(4) . .
C12 N1 C15 120.5(4) . .
C13 N1 C15 119.8(4) . .
F2 C6 F1 105.7(5) . .
F2 C6 C5 115.7(4) . .
F1 C6 C5 111.3(4) . .
F2 C6 C7 109.6(4) . .
F1 C6 C7 107.7(4) . .
C5 C6 C7 106.5(5) . .
F3 C7 F3 106.0(7) . 2
F3 C7 C6 111.2(3) . 2
F3 C7 C6 112.1(3) 2 2
F3 C7 C6 112.1(3) . .
F3 C7 C6 111.2(3) 2 .
C6 C7 C6 104.4(6) 2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 F8 1.542(3) .
P1 F4 1.554(3) .
P1 F7 1.574(3) .
P1 F9 1.584(3) .
P1 F5 1.585(3) .
P1 F6 1.589(3) .
S1 C1 1.726(4) .
S1 C4 1.731(4) .
C2 C1 1.381(5) .
C2 C3 1.407(4) .
C2 C5 1.475(5) .
C1 C8 1.411(5) .
C3 C4 1.363(5) .
C3 H3 0.9500 .
C5 C5 1.309(7) 2
C5 C6 1.496(6) .
C4 C16 1.478(5) .
C9 C8 1.178(5) .
C9 C10 1.450(5) .
C13 N1 1.333(5) .
C13 C14 1.374(5) .
C13 H13 0.9500 .
C10 C11 1.365(6) .
C10 C14 1.380(5) .
C11 C12 1.373(5) .
C11 H11 0.9500 .
C16 C21 1.357(5) .
C16 C17 1.383(6) .
C19 C20 1.355(6) .
C19 C18 1.364(6) .
C19 H19 0.9500 .
C12 N1 1.321(5) .
C12 H12 0.9500 .
C18 C17 1.390(5) .
C18 H18 0.9500 .
C14 H14 0.9500 .
C17 H17 0.9500 .
C21 C20 1.392(5) .
C21 H21 0.9500 .
C15 N1 1.473(4) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C20 H20 0.9500 .
C6 F2 1.297(5) .
C6 F1 1.336(5) .
C6 C7 1.515(6) .
C7 F3 1.287(5) .
C7 F3 1.287(5) 2
C7 C6 1.515(6) 2
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139038694
