#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:14:47 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180295 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/09/7150970.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_7150970
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_sum            'C25 H16 O2 S'
_chemical_formula_weight         380.44
_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                 101.498(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1939(5)
_cell_length_b                   14.0344(4)
_cell_length_c                   11.7187(5)
_cell_measurement_reflns_used    4256
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     1804.06(12)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0999
_diffrn_reflns_av_sigmaI/netI    0.0894
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21913
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.16
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_correction_T_min  0.9843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Shard
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4135
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0671
_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)+(0.0291P)²+1.8406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1255
_reflns_number_gt                2928
_reflns_number_total             4135
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b807744d.txt
_cod_data_source_block           2006src0408
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7150970
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
C1 C 0.4114(2) 0.24667(17) 0.6498(2) 0.0198(6) Uani 1 1 d . . .
C2 C 0.5268(2) 0.27530(17) 0.6096(2) 0.0209(6) Uani 1 1 d . . .
H2 H 0.5754 0.2279 0.5831 0.025 Uiso 1 1 calc R . .
C3 C 0.5607(2) 0.36610(17) 0.6108(2) 0.0206(6) Uani 1 1 d . . .
H3 H 0.6362 0.3828 0.5908 0.025 Uiso 1 1 calc R . .
C4 C 0.4823(2) 0.43997(17) 0.6429(2) 0.0189(5) Uani 1 1 d . . .
C5 C 0.3648(2) 0.41431(17) 0.6477(2) 0.0195(6) Uani 1 1 d . . .
C6 C 0.2779(2) 0.48000(17) 0.6691(2) 0.0228(6) Uani 1 1 d . . .
H6 H 0.1974 0.4598 0.6711 0.027 Uiso 1 1 calc R . .
C7 C 0.3101(3) 0.57378(18) 0.6871(2) 0.0247(6) Uani 1 1 d . . .
H7 H 0.2511 0.6185 0.7013 0.030 Uiso 1 1 calc R . .
C8 C 0.4296(2) 0.60513(17) 0.6851(2) 0.0215(6) Uani 1 1 d . . .
C9 C 0.4636(3) 0.70210(18) 0.7044(2) 0.0230(6) Uani 1 1 d . . .
H9 H 0.4051 0.7468 0.7198 0.028 Uiso 1 1 calc R . .
C10 C 0.5781(3) 0.73203(18) 0.7014(2) 0.0253(6) Uani 1 1 d . . .
H10 H 0.5994 0.7973 0.7136 0.030 Uiso 1 1 calc R . .
C11 C 0.6651(2) 0.66554(18) 0.6798(2) 0.0237(6) Uani 1 1 d . . .
H11 H 0.7455 0.6864 0.6782 0.028 Uiso 1 1 calc R . .
C12 C 0.6361(2) 0.57130(17) 0.6612(2) 0.0207(6) Uani 1 1 d . . .
H12 H 0.6964 0.5278 0.6469 0.025 Uiso 1 1 calc R . .
C13 C 0.5173(2) 0.53797(17) 0.6632(2) 0.0191(6) Uani 1 1 d . . .
C14 C 0.3514(2) 0.15947(17) 0.5840(2) 0.0194(6) Uani 1 1 d . . .
C15 C 0.4061(2) 0.07025(18) 0.6082(2) 0.0204(6) Uani 1 1 d . . .
C16 C 0.3557(3) -0.01178(18) 0.5534(2) 0.0253(6) Uani 1 1 d . . .
H16 H 0.3946 -0.0716 0.5714 0.030 Uiso 1 1 calc R . .
C17 C 0.2478(3) -0.00577(19) 0.4719(2) 0.0279(7) Uani 1 1 d . . .
H17 H 0.2125 -0.0614 0.4328 0.033 Uiso 1 1 calc R . .
C18 C 0.1918(3) 0.08193(19) 0.4477(2) 0.0285(7) Uani 1 1 d . . .
H18 H 0.1176 0.0861 0.3919 0.034 Uiso 1 1 calc R . .
C19 C 0.2423(3) 0.16390(19) 0.5037(2) 0.0244(6) Uani 1 1 d . . .
H19 H 0.2020 0.2233 0.4870 0.029 Uiso 1 1 calc R . .
C20 C 0.4408(2) 0.22228(17) 0.7804(2) 0.0182(5) Uani 1 1 d . . .
C21 C 0.5012(2) 0.13744(17) 0.8158(2) 0.0190(6) Uani 1 1 d . . .
C22 C 0.5271(2) 0.10876(18) 0.9312(2) 0.0228(6) Uani 1 1 d . . .
H22 H 0.5699 0.0510 0.9530 0.027 Uiso 1 1 calc R . .
C23 C 0.4896(3) 0.16573(18) 1.0145(2) 0.0250(6) Uani 1 1 d . . .
H23 H 0.5055 0.1468 1.0939 0.030 Uiso 1 1 calc R . .
C24 C 0.4288(3) 0.25006(19) 0.9811(2) 0.0257(6) Uani 1 1 d . . .
H24 H 0.4036 0.2891 1.0382 0.031 Uiso 1 1 calc R . .
C25 C 0.4041(2) 0.27860(18) 0.8648(2) 0.0224(6) Uani 1 1 d . . .
H25 H 0.3620 0.3367 0.8431 0.027 Uiso 1 1 calc R . .
O1 O 0.32327(16) 0.32181(11) 0.62904(15) 0.0211(4) Uani 1 1 d . . .
O11 O 0.55634(18) -0.03835(12) 0.75931(16) 0.0297(5) Uani 1 1 d . . .
S1 S 0.54759(6) 0.05989(4) 0.71052(6) 0.02161(17) 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
O1 C1 C2 110.7(2) . . ?
O1 C1 C14 106.6(2) . . ?
C2 C1 C14 111.8(2) . . ?
O1 C1 C20 109.7(2) . . ?
C2 C1 C20 110.0(2) . . ?
C14 C1 C20 108.02(19) . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C13 118.4(2) . . ?
C5 C4 C3 117.1(2) . . ?
C13 C4 C3 124.5(2) . . ?
C4 C5 O1 122.3(2) . . ?
C4 C5 C6 122.6(2) . . ?
O1 C5 C6 115.1(2) . . ?
C7 C6 C5 119.3(3) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C8 121.2(2) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C9 121.4(2) . . ?
C7 C8 C13 119.2(2) . . ?
C9 C8 C13 119.5(2) . . ?
C10 C9 C8 121.2(3) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C11 119.4(2) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 120.8(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C8 118.0(2) . . ?
C12 C13 C4 122.7(2) . . ?
C8 C13 C4 119.3(2) . . ?
C19 C14 C15 117.9(2) . . ?
C19 C14 C1 123.1(2) . . ?
C15 C14 C1 119.0(2) . . ?
C16 C15 C14 122.0(2) . . ?
C16 C15 S1 117.9(2) . . ?
C14 C15 S1 120.09(19) . . ?
C15 C16 C17 119.3(2) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C18 119.5(2) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C19 121.0(3) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C14 C19 C18 120.3(2) . . ?
C14 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C25 C20 C21 118.0(2) . . ?
C25 C20 C1 123.1(2) . . ?
C21 C20 C1 118.8(2) . . ?
C22 C21 C20 122.3(2) . . ?
C22 C21 S1 117.45(19) . . ?
C20 C21 S1 120.24(19) . . ?
C21 C22 C23 119.0(2) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
C24 C23 C22 119.6(2) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C23 C24 C25 120.9(3) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C20 C25 C24 120.2(2) . . ?
C20 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C5 O1 C1 117.80(19) . . ?
O11 S1 C15 108.29(12) . . ?
O11 S1 C21 107.64(11) . . ?
C15 S1 C21 94.15(12) . . ?
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
C1 O1 1.432(3) . ?
C1 C2 1.515(4) . ?
C1 C14 1.529(3) . ?
C1 C20 1.538(3) . ?
C2 C3 1.329(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.455(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(4) . ?
C4 C13 1.437(3) . ?
C5 O1 1.382(3) . ?
C5 C6 1.399(4) . ?
C6 C7 1.370(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.413(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.419(3) . ?
C8 C13 1.421(4) . ?
C9 C10 1.356(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.408(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.369(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.413(4) . ?
C12 H12 0.9500 . ?
C14 C19 1.386(4) . ?
C14 C15 1.398(3) . ?
C15 C16 1.383(4) . ?
C15 S1 1.792(3) . ?
C16 C17 1.385(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C25 1.390(4) . ?
C20 C21 1.391(3) . ?
C21 C22 1.385(4) . ?
C21 S1 1.798(3) . ?
C22 C23 1.390(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.395(4) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
O11 S1 1.4884(18) . ?
