#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/09/7150968.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_7150968
loop_
_publ_author_name
'Gabbutt, Christopher D.'
'Heron, B. Mark'
'Kolla, Suresh B.'
'Kilner, Colin'
'Coles, Simon J.'
'Horton, Peter N.'
'Hursthouse, Michael B.'
_publ_section_title
;
 Ring contraction during the 6π-electrocyclisation of naphthopyran
 valence tautomers
;
_journal_issue                   17
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              3096
_journal_page_last               3104
_journal_paper_doi               10.1039/b807744d
_journal_volume                  6
_journal_year                    2008
_chemical_formula_moiety         'C25 H16 O3 S'
_chemical_formula_sum            'C25 H16 O3 S'
_chemical_formula_weight         396.44
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 101.1430(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.97170(10)
_cell_length_b                   20.6854(3)
_cell_length_c                   11.1804(2)
_cell_measurement_reflns_used    24270
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1808.87(5)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1996)'
_computing_data_collection       'COLLECT (Nonius, 2004)'
_computing_data_reduction
;
DENZO-SMN and COLLECT (Otwinowski & Minor, 1996)
;
_computing_molecular_graphics
;
ORTEP-III Version 1.08 (Farrugia, 2005)
;
_computing_publication_material
;
enCIFer: A program for viewing, editing and visualising CIFs.
F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler,
J. Applied Cryst., 37, 331-334, 2004
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
SIR92
Altomare, A.; Burla, M. C.; Camalli, G.; Cascarano, G.;
Giacovazzo, C.; Guagliardi, A.; Polidori, G.
J. Appl. Cryst. 1994, 27, 435-436.
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Nonius KappaCCD area-detector diffractometer
;
_diffrn_measurement_method
;
phi and omega scans to fill the asymmetric unit
;
_diffrn_radiation_detector       'CCD plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            34563
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.71
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale brown'
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3553
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0568P)²+0.7477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1084
_reflns_number_gt                3006
_reflns_number_total             3553
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b807744d.txt
_cod_data_source_block           compound_6
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7150968
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.0489(2) 0.13082(8) 0.58869(15) 0.0235(3) Uani 1 1 d . . .
C3 C -0.0433(2) 0.07723(8) 0.61410(16) 0.0274(4) Uani 1 1 d . . .
H3 H -0.0646 0.0422 0.5582 0.033 Uiso 1 1 calc R . .
C4 C -0.1040(2) 0.07560(9) 0.72240(17) 0.0319(4) Uani 1 1 d . . .
H4 H -0.1680 0.0395 0.7410 0.038 Uiso 1 1 calc R . .
C5 C -0.0707(2) 0.12675(9) 0.80305(17) 0.0332(4) Uani 1 1 d . . .
H5 H -0.1121 0.1255 0.8772 0.040 Uiso 1 1 calc R . .
C6 C 0.0225(2) 0.17992(9) 0.77695(16) 0.0303(4) Uani 1 1 d . . .
H6 H 0.0447 0.2145 0.8337 0.036 Uiso 1 1 calc R . .
C7 C 0.0838(2) 0.18307(8) 0.66852(15) 0.0250(4) Uani 1 1 d . . .
C8 C 0.1929(2) 0.24046(8) 0.64353(15) 0.0249(4) Uani 1 1 d . . .
H8 H 0.2479 0.2582 0.7249 0.030 Uiso 1 1 calc R . .
C9 C 0.3376(2) 0.22073(8) 0.58009(15) 0.0247(3) Uani 1 1 d . . .
C10 C 0.4977(2) 0.24949(8) 0.61307(16) 0.0290(4) Uani 1 1 d . . .
H10 H 0.5144 0.2831 0.6721 0.035 Uiso 1 1 calc R . .
C11 C 0.6332(2) 0.22957(9) 0.56053(16) 0.0310(4) Uani 1 1 d . . .
H11 H 0.7418 0.2496 0.5843 0.037 Uiso 1 1 calc R . .
C12 C 0.6118(2) 0.18074(9) 0.47357(16) 0.0302(4) Uani 1 1 d . . .
H12 H 0.7052 0.1676 0.4379 0.036 Uiso 1 1 calc R . .
C13 C 0.4538(2) 0.15134(8) 0.43919(15) 0.0269(4) Uani 1 1 d . . .
H13 H 0.4377 0.1176 0.3804 0.032 Uiso 1 1 calc R . .
C14 C 0.3188(2) 0.17204(8) 0.49231(15) 0.0237(3) Uani 1 1 d . . .
C81 C 0.0899(2) 0.29479(8) 0.57579(15) 0.0252(4) Uani 1 1 d . . .
C83 C -0.0906(2) 0.37632(8) 0.56695(15) 0.0258(4) Uani 1 1 d . . .
C84 C -0.2032(2) 0.42233(8) 0.59899(16) 0.0299(4) Uani 1 1 d . . .
H84 H -0.2410 0.4203 0.6744 0.036 Uiso 1 1 calc R . .
C85 C -0.2557(2) 0.47026(8) 0.51609(16) 0.0313(4) Uani 1 1 d . . .
H85 H -0.3313 0.5025 0.5350 0.038 Uiso 1 1 calc R . .
C86 C -0.2008(2) 0.47355(8) 0.40192(16) 0.0292(4) Uani 1 1 d . . .
C87 C -0.2518(2) 0.52486(9) 0.31879(17) 0.0340(4) Uani 1 1 d . . .
H87 H -0.3241 0.5579 0.3391 0.041 Uiso 1 1 calc R . .
C88 C -0.1984(2) 0.52750(9) 0.20985(17) 0.0363(4) Uani 1 1 d . . .
H88 H -0.2338 0.5623 0.1554 0.044 Uiso 1 1 calc R . .
C89 C -0.0918(2) 0.47918(9) 0.17771(17) 0.0353(4) Uani 1 1 d . . .
H89 H -0.0552 0.4816 0.1019 0.042 Uiso 1 1 calc R . .
C90 C -0.0399(2) 0.42839(9) 0.25535(16) 0.0310(4) Uani 1 1 d . . .
H90 H 0.0307 0.3955 0.2322 0.037 Uiso 1 1 calc R . .
C91 C -0.0911(2) 0.42478(8) 0.36944(15) 0.0269(4) Uani 1 1 d . . .
C92 C -0.0360(2) 0.37519(8) 0.45706(15) 0.0258(4) Uani 1 1 d . . .
C93 C 0.0800(2) 0.32136(8) 0.46433(16) 0.0265(4) Uani 1 1 d . . .
H93 H 0.1384 0.3073 0.4026 0.032 Uiso 1 1 calc R . .
O1 O 0.00372(15) 0.17374(6) 0.36649(11) 0.0317(3) Uani 1 1 d . . .
O2 O 0.14789(16) 0.06870(6) 0.40829(11) 0.0319(3) Uani 1 1 d . . .
O82 O -0.01454(14) 0.32724(5) 0.64175(10) 0.0263(3) Uani 1 1 d . . .
S1 S 0.11952(5) 0.133079(19) 0.44924(4) 0.02435(14) 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'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
C3 C2 C7 122.38(15) . . ?
C3 C2 S1 118.38(13) . . ?
C7 C2 S1 119.22(12) . . ?
C4 C3 C2 119.00(16) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 C3 119.68(16) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.79(16) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C7 120.76(17) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C2 117.38(15) . . ?
C6 C7 C8 120.19(15) . . ?
C2 C7 C8 122.35(14) . . ?
C81 C8 C9 110.76(13) . . ?
C81 C8 C7 113.38(13) . . ?
C9 C8 C7 112.70(13) . . ?
C81 C8 H8 106.5 . . ?
C9 C8 H8 106.5 . . ?
C7 C8 H8 106.5 . . ?
C10 C9 C14 117.62(15) . . ?
C10 C9 C8 120.04(15) . . ?
C14 C9 C8 122.28(15) . . ?
C11 C10 C9 120.64(16) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.76(16) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 119.73(16) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 118.86(16) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C13 C14 C9 122.38(15) . . ?
C13 C14 S1 118.20(13) . . ?
C9 C14 S1 119.40(12) . . ?
C93 C81 O82 111.09(15) . . ?
C93 C81 C8 134.12(15) . . ?
O82 C81 C8 114.74(13) . . ?
O82 C83 C92 110.49(14) . . ?
O82 C83 C84 124.97(15) . . ?
C92 C83 C84 124.51(16) . . ?
C85 C84 C83 116.54(16) . . ?
C85 C84 H84 121.7 . . ?
C83 C84 H84 121.7 . . ?
C84 C85 C86 122.27(16) . . ?
C84 C85 H85 118.9 . . ?
C86 C85 H85 118.9 . . ?
C87 C86 C91 118.33(16) . . ?
C87 C86 C85 121.53(16) . . ?
C91 C86 C85 120.14(15) . . ?
C88 C87 C86 121.01(17) . . ?
C88 C87 H87 119.5 . . ?
C86 C87 H87 119.5 . . ?
C87 C88 C89 120.53(17) . . ?
C87 C88 H88 119.7 . . ?
C89 C88 H88 119.7 . . ?
C90 C89 C88 120.39(17) . . ?
C90 C89 H89 119.8 . . ?
C88 C89 H89 119.8 . . ?
C89 C90 C91 120.39(17) . . ?
C89 C90 H90 119.8 . . ?
C91 C90 H90 119.8 . . ?
C90 C91 C86 119.34(16) . . ?
C90 C91 C92 123.54(16) . . ?
C86 C91 C92 117.11(15) . . ?
C83 C92 C91 119.37(15) . . ?
C83 C92 C93 105.80(15) . . ?
C91 C92 C93 134.70(16) . . ?
C81 C93 C92 106.79(15) . . ?
C81 C93 H93 126.6 . . ?
C92 C93 H93 126.6 . . ?
C83 O82 C81 105.80(12) . . ?
O2 S1 O1 117.08(8) . . ?
O2 S1 C2 110.75(7) . . ?
O1 S1 C2 108.00(7) . . ?
O2 S1 C14 108.71(8) . . ?
O1 S1 C14 109.84(7) . . ?
C2 S1 C14 101.31(8) . . ?
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
C2 C3 1.389(2) . ?
C2 C7 1.395(2) . ?
C2 S1 1.7578(16) . ?
C3 C4 1.388(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.529(2) . ?
C8 C81 1.507(2) . ?
C8 C9 1.522(2) . ?
C8 H8 1.0000 . ?
C9 C10 1.392(2) . ?
C9 C14 1.394(2) . ?
C10 C11 1.388(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.393(2) . ?
C13 H13 0.9500 . ?
C14 S1 1.7635(16) . ?
C81 C93 1.350(2) . ?
C81 O82 1.3871(19) . ?
C83 O82 1.379(2) . ?
C83 C92 1.380(2) . ?
C83 C84 1.401(2) . ?
C84 C85 1.367(2) . ?
C84 H84 0.9500 . ?
C85 C86 1.429(2) . ?
C85 H85 0.9500 . ?
C86 C87 1.418(2) . ?
C86 C91 1.427(2) . ?
C87 C88 1.367(3) . ?
C87 H87 0.9500 . ?
C88 C89 1.403(3) . ?
C88 H88 0.9500 . ?
C89 C90 1.375(3) . ?
C89 H89 0.9500 . ?
C90 C91 1.414(2) . ?
C90 H90 0.9500 . ?
C91 C92 1.428(2) . ?
C92 C93 1.440(2) . ?
C93 H93 0.9500 . ?
O1 S1 1.4441(12) . ?
O2 S1 1.4402(12) . ?
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
C7 C2 C3 C4 0.4(2) . . . . ?
S1 C2 C3 C4 -178.25(13) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C5 C6 C7 C2 -0.4(2) . . . . ?
C5 C6 C7 C8 -177.28(16) . . . . ?
C3 C2 C7 C6 0.1(2) . . . . ?
S1 C2 C7 C6 178.71(12) . . . . ?
C3 C2 C7 C8 176.84(15) . . . . ?
S1 C2 C7 C8 -4.5(2) . . . . ?
C6 C7 C8 C81 -91.71(18) . . . . ?
C2 C7 C8 C81 91.61(18) . . . . ?
C6 C7 C8 C9 141.46(16) . . . . ?
C2 C7 C8 C9 -35.2(2) . . . . ?
C81 C8 C9 C10 91.41(18) . . . . ?
C7 C8 C9 C10 -140.38(16) . . . . ?
C81 C8 C9 C14 -91.58(18) . . . . ?
C7 C8 C9 C14 36.6(2) . . . . ?
C14 C9 C10 C11 -0.5(2) . . . . ?
C8 C9 C10 C11 176.60(15) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C14 0.6(2) . . . . ?
C12 C13 C14 C9 -0.9(2) . . . . ?
C12 C13 C14 S1 -178.95(13) . . . . ?
C10 C9 C14 C13 0.8(2) . . . . ?
C8 C9 C14 C13 -176.23(15) . . . . ?
C10 C9 C14 S1 178.91(12) . . . . ?
C8 C9 C14 S1 1.8(2) . . . . ?
C9 C8 C81 C93 13.2(3) . . . . ?
C7 C8 C81 C93 -114.6(2) . . . . ?
C9 C8 C81 O82 -163.87(13) . . . . ?
C7 C8 C81 O82 68.28(18) . . . . ?
O82 C83 C84 C85 175.23(15) . . . . ?
C92 C83 C84 C85 -2.6(3) . . . . ?
C83 C84 C85 C86 0.5(3) . . . . ?
C84 C85 C86 C87 -177.77(16) . . . . ?
C84 C85 C86 C91 1.8(3) . . . . ?
C91 C86 C87 C88 0.4(2) . . . . ?
C85 C86 C87 C88 179.99(16) . . . . ?
C86 C87 C88 C89 0.1(3) . . . . ?
C87 C88 C89 C90 0.2(3) . . . . ?
C88 C89 C90 C91 -1.1(3) . . . . ?
C89 C90 C91 C86 1.6(2) . . . . ?
C89 C90 C91 C92 -177.00(16) . . . . ?
C87 C86 C91 C90 -1.3(2) . . . . ?
C85 C86 C91 C90 179.17(15) . . . . ?
C87 C86 C91 C92 177.42(15) . . . . ?
C85 C86 C91 C92 -2.2(2) . . . . ?
O82 C83 C92 C91 -175.90(14) . . . . ?
C84 C83 C92 C91 2.2(3) . . . . ?
O82 C83 C92 C93 0.63(18) . . . . ?
C84 C83 C92 C93 178.69(16) . . . . ?
C90 C91 C92 C83 178.90(15) . . . . ?
C86 C91 C92 C83 0.3(2) . . . . ?
C90 C91 C92 C93 3.6(3) . . . . ?
C86 C91 C92 C93 -175.02(17) . . . . ?
O82 C81 C93 C92 0.89(19) . . . . ?
C8 C81 C93 C92 -176.26(17) . . . . ?
C83 C92 C93 C81 -0.91(18) . . . . ?
C91 C92 C93 C81 174.83(18) . . . . ?
C92 C83 O82 C81 -0.11(17) . . . . ?
C84 C83 O82 C81 -178.16(16) . . . . ?
C93 C81 O82 C83 -0.50(18) . . . . ?
C8 C81 O82 C83 177.24(13) . . . . ?
C3 C2 S1 O2 -29.02(15) . . . . ?
C7 C2 S1 O2 152.29(13) . . . . ?
C3 C2 S1 O1 100.39(14) . . . . ?
C7 C2 S1 O1 -78.30(14) . . . . ?
C3 C2 S1 C14 -144.21(13) . . . . ?
C7 C2 S1 C14 37.10(14) . . . . ?
C13 C14 S1 O2 25.58(15) . . . . ?
C9 C14 S1 O2 -152.56(13) . . . . ?
C13 C14 S1 O1 -103.70(14) . . . . ?
C9 C14 S1 O1 78.16(14) . . . . ?
C13 C14 S1 C2 142.28(13) . . . . ?
C9 C14 S1 C2 -35.86(14) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25938746
