##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2011-09-07
_journal_date_accepted     2011-09-12
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue     10
_journal_page_first     o2764
_journal_page_last     o2765
_journal_paper_category     QO
_journal_coeditor_code     SU2314
_publ_contact_author_name     'Professor Jim Simpson'
_publ_contact_author_address
;
Department of Chemistry
  University of Otago
  P.O. Box 56
  Dunedin
  New Zealand
;
_publ_contact_author_email     jsimpson@alkali.otago.ac.nz
_publ_contact_author_fax     '+64-3-04797906'
_publ_contact_author_phone     '+64-3-4797914 '
_publ_section_title
;\
Ethyl
5-hydroxy-6-oxo-4-phenyl-5,6-dihydro-4H-cyclopenta[b]\
thiophene-5-carboxylate
;
loop_
    _publ_author_name
    _publ_author_address
    'McAdam, C. John'
;       Department of Chemistry
        University of Otago
        PO Box 56
        Dunedin
        New Zealand
;
    'Moratti, Stephen C.'
;       Department of Chemistry
        University of Otago
        PO Box 56
        Dunedin
        New Zealand
;
    'Simpson, Jim'
;       Department of Chemistry
        University of Otago
        PO Box 56
        Dunedin
        New Zealand
;
    'Shi, Zheng'
;       Department of Chemistry
        University of Otago
        PO Box 56
        Dunedin
        New Zealand
;
data_I
_chemical_name_systematic
;
Ethyl 5-hydroxy-6-oxo-4-phenyl-5,6-dihydro-4H-
cyclopenta[b]thiophene-5-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H14 O4 S'
_chemical_formula_sum     'C16 H14 O4 S'
_chemical_formula_iupac     'C16 H14 O4 S'
_chemical_formula_weight     302.33
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.7407(4)
_cell_length_b     9.1005(4)
_cell_length_c     10.5035(5)
_cell_angle_alpha     84.840(3)
_cell_angle_beta     80.929(3)
_cell_angle_gamma     88.086(3)
_cell_volume     727.56(6)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     4122
_cell_measurement_theta_min     2.67
_cell_measurement_theta_max     24.90
_cell_measurement_temperature     91(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.35
_exptl_crystal_size_min     0.25
_exptl_crystal_density_diffrn     1.380
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     316
_exptl_absorpt_coefficient_mu     0.235
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2011)'
_exptl_absorpt_correction_T_min     0.6724
_exptl_absorpt_correction_T_max     0.7452
_exptl_special_details
;
Spectroscopic data for the title compound:
¹H NMR (δ p.p.m., CDCl₃, 400 MHz): 8.08 (1H, d, J = 4.8 Hz,
 CHS),
7.35--7.28 (5H, m, phenyl H),
7.16 (1H, d, J = 4.8 Hz,
CHCHS), 4.73 (1H, s, CHC₆H₅), 4.37 (1H, s,
OH), 3.82 & 3.62 [2 x (1H, m, CH₂)], 0.85
(3H, t, J = 7 Hz, CH₃). IR ν(CO) 1737, 1703 cm⁻¹
.
;
_diffrn_ambient_temperature     91(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     13007
_diffrn_reflns_av_R_equivalents     0.0350
_diffrn_reflns_av_sigmaI/netI     0.0285
_diffrn_reflns_theta_min     2.67
_diffrn_reflns_theta_max     25.18
_diffrn_reflns_theta_full     25.18
_diffrn_measured_fraction_theta_max     0.987
_diffrn_measured_fraction_theta_full     0.987
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2584
_reflns_number_gt     2233
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0391
_refine_ls_R_factor_gt     0.0320
_refine_ls_wR_factor_gt     0.0751
_refine_ls_wR_factor_ref     0.0791
_refine_ls_goodness_of_fit_ref     1.069
_refine_ls_restrained_S_all     1.069
_refine_ls_number_reflns     2584
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0322P)²+0.3338P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.296
_refine_diff_density_min     -0.259
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2011)'
_computing_cell_refinement     'APEX2 and SAINT (Bruker, 2011)'
_computing_data_reduction     'SAINT (Bruker, 2011)'
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008) and  TITAN2000 (Hunter & Simpson,
1999)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004),
PLATON (Spek, 2009)
and publCIF (Westrip 2010)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.31491(5) 0.47012(4) 0.41577(4) 0.01868(13) Uani d . 1 1 . .
    C C1 0.2877(2) 0.33654(18) 0.54308(16) 0.0206(4) Uani d . 1 1 . .
    H H1 0.3238 0.2366 0.5349 0.025 Uiso calc R 1 1 . .
    C C2 0.2095(2) 0.38688(18) 0.65715(16) 0.0185(4) Uani d . 1 1 . .
    H H2 0.1850 0.3271 0.7365 0.022 Uiso calc R 1 1 . .
    C C3 0.1697(2) 0.53999(17) 0.64162(15) 0.0149(3) Uani d . 1 1 . .
    C C4 0.2184(2) 0.59827(17) 0.51632(15) 0.0155(3) Uani d . 1 1 . .
    C C5 0.1669(2) 0.75165(17) 0.49802(15) 0.0154(3) Uani d . 1 1 . .
    O O5 0.17464(15) 0.83394(12) 0.39918(10) 0.0204(3) Uani d . 1 1 . .
    C C6 0.0911(2) 0.79820(17) 0.63548(15) 0.0152(3) Uani d . 1 1 . .
    O O6 -0.07237(14) 0.86931(13) 0.63575(12) 0.0203(3) Uani d . 1 1 . .
    H H6 -0.064(3) 0.959(2) 0.6268(19) 0.030 Uiso d . 1 1 . .
    C C7 0.0721(2) 0.65116(17) 0.72591(15) 0.0158(3) Uani d . 1 1 . .
    H H7 -0.0542 0.6251 0.7382 0.019 Uiso calc R 1 1 . .
    C C8 0.1173(2) 0.66251(18) 0.86036(15) 0.0174(4) Uani d . 1 1 . .
    C C9 0.2418(2) 0.57266(19) 0.91240(16) 0.0228(4) Uani d . 1 1 . .
    H H9 0.3044 0.5001 0.8629 0.027 Uiso calc R 1 1 . .
    C C10 0.2752(3) 0.5886(2) 1.03705(17) 0.0293(4) Uani d . 1 1 . .
    H H10 0.3582 0.5247 1.0728 0.035 Uiso calc R 1 1 . .
    C C11 0.1892(3) 0.6958(2) 1.10879(17) 0.0292(4) Uani d . 1 1 . .
    H H11 0.2145 0.7074 1.1929 0.035 Uiso calc R 1 1 . .
    C C12 0.0658(3) 0.78667(19) 1.05765(17) 0.0272(4) Uani d . 1 1 . .
    H H12 0.0067 0.8614 1.1064 0.033 Uiso calc R 1 1 . .
    C C13 0.0281(2) 0.76864(18) 0.93510(16) 0.0216(4) Uani d . 1 1 . .
    H H13 -0.0595 0.8293 0.9017 0.026 Uiso calc R 1 1 . .
    C C14 0.2214(2) 0.90456(17) 0.67132(14) 0.0147(3) Uani d . 1 1 . .
    O O14 0.18207(15) 1.02944(12) 0.69500(11) 0.0212(3) Uani d . 1 1 . .
    O O15 0.38114(14) 0.84388(12) 0.66685(11) 0.0200(3) Uani d . 1 1 . .
    C C15 0.5156(2) 0.9380(2) 0.69937(17) 0.0245(4) Uani d . 1 1 . .
    H H15A 0.4980 1.0404 0.6625 0.029 Uiso calc R 1 1 . .
    H H15B 0.6326 0.9028 0.6600 0.029 Uiso calc R 1 1 . .
    C C16 0.5090(3) 0.9368(3) 0.8421(2) 0.0471(6) Uani d . 1 1 . .
    H H16A 0.3957 0.9768 0.8807 0.071 Uiso calc R 1 1 . .
    H H16B 0.6030 0.9975 0.8603 0.071 Uiso calc R 1 1 . .
    H H16C 0.5241 0.8353 0.8790 0.071 Uiso calc R 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 C1 . 1.7164(17) ?
    S1 C4 . 1.7171(16) ?
    C1 C2 . 1.365(2) ?
    C1 H1 . 0.9500 ?
    C2 C3 . 1.417(2) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.374(2) ?
    C3 C7 . 1.509(2) ?
    C4 C5 . 1.443(2) ?
    C5 O5 . 1.2190(19) ?
    C5 C6 . 1.560(2) ?
    C6 O6 . 1.4018(18) ?
    C6 C14 . 1.531(2) ?
    C6 C7 . 1.567(2) ?
    O6 H6 . 0.82(2) ?
    C7 C8 . 1.520(2) ?
    C7 H7 . 1.0000 ?
    C8 C9 . 1.389(2) ?
    C8 C13 . 1.395(2) ?
    C9 C10 . 1.395(2) ?
    C9 H9 . 0.9500 ?
    C10 C11 . 1.376(3) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.384(3) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.389(2) ?
    C12 H12 . 0.9500 ?
    C13 H13 . 0.9500 ?
    C14 O14 . 1.2041(19) ?
    C14 O15 . 1.3332(19) ?
    O15 C15 . 1.4689(19) ?
    C15 C16 . 1.491(3) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C16 H16A . 0.9800 ?
    C16 H16B . 0.9800 ?
    C16 H16C . 0.9800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 S1 C4 . . 89.88(8) ?
    C2 C1 S1 . . 113.94(13) ?
    C2 C1 H1 . . 123.0 ?
    S1 C1 H1 . . 123.0 ?
    C1 C2 C3 . . 111.12(15) ?
    C1 C2 H2 . . 124.4 ?
    C3 C2 H2 . . 124.4 ?
    C4 C3 C2 . . 112.06(14) ?
    C4 C3 C7 . . 112.16(14) ?
    C2 C3 C7 . . 135.47(15) ?
    C3 C4 C5 . . 112.25(14) ?
    C3 C4 S1 . . 112.99(12) ?
    C5 C4 S1 . . 134.64(13) ?
    O5 C5 C4 . . 130.13(15) ?
    O5 C5 C6 . . 124.00(14) ?
    C4 C5 C6 . . 105.87(13) ?
    O6 C6 C14 . . 109.60(13) ?
    O6 C6 C5 . . 111.05(12) ?
    C14 C6 C5 . . 106.85(12) ?
    O6 C6 C7 . . 110.20(12) ?
    C14 C6 C7 . . 113.48(12) ?
    C5 C6 C7 . . 105.56(12) ?
    C6 O6 H6 . . 111.8(14) ?
    C3 C7 C8 . . 119.14(13) ?
    C3 C7 C6 . . 102.88(12) ?
    C8 C7 C6 . . 114.66(13) ?
    C3 C7 H7 . . 106.4 ?
    C8 C7 H7 . . 106.4 ?
    C6 C7 H7 . . 106.4 ?
    C9 C8 C13 . . 118.56(15) ?
    C9 C8 C7 . . 123.45(14) ?
    C13 C8 C7 . . 117.99(15) ?
    C8 C9 C10 . . 120.27(16) ?
    C8 C9 H9 . . 119.9 ?
    C10 C9 H9 . . 119.9 ?
    C11 C10 C9 . . 120.64(17) ?
    C11 C10 H10 . . 119.7 ?
    C9 C10 H10 . . 119.7 ?
    C10 C11 C12 . . 119.60(16) ?
    C10 C11 H11 . . 120.2 ?
    C12 C11 H11 . . 120.2 ?
    C11 C12 C13 . . 120.06(16) ?
    C11 C12 H12 . . 120.0 ?
    C13 C12 H12 . . 120.0 ?
    C12 C13 C8 . . 120.82(17) ?
    C12 C13 H13 . . 119.6 ?
    C8 C13 H13 . . 119.6 ?
    O14 C14 O15 . . 125.38(15) ?
    O14 C14 C6 . . 122.73(14) ?
    O15 C14 C6 . . 111.83(13) ?
    C14 O15 C15 . . 115.81(12) ?
    O15 C15 C16 . . 111.60(15) ?
    O15 C15 H15A . . 109.3 ?
    C16 C15 H15A . . 109.3 ?
    O15 C15 H15B . . 109.3 ?
    C16 C15 H15B . . 109.3 ?
    H15A C15 H15B . . 108.0 ?
    C15 C16 H16A . . 109.5 ?
    C15 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C15 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    O6 H6 O14 . 0.82(2) 2.27(2) 2.6705(16) 110.8(16)
    O6 H6 O5 2_576 0.82(2) 2.06(2) 2.7973(16) 150.5(19)
    C1 H1 O14 1_545 0.95 2.56 3.157(2) 121
    C11 H11 O5 1_556 0.95 2.52 3.386(2) 152
    C15 H15B O6 1_655 0.99 2.27 3.206(2) 157
    C7 H7 S1 2_566 1.00 2.97 3.7855(16) 139
    C12 H12 O14 2_577 0.95 2.61 3.497(2) 157
