#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/21/2222164.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222164
loop_
_publ_author_name
'Xu, Shiqing'
'Chen, Ying'
'Xia, Peng'
_publ_section_title
;
 9-Isopropenyl-4-methyl-2H-thieno[2,3-h]chromen-2-one
;
_journal_coeditor_code           TK2449
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1311
_journal_paper_doi               10.1107/S1600536809017930
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H12 O2 S'
_chemical_formula_moiety         'C15 H12 O2 S'
_chemical_formula_sum            'C15 H12 O2 S'
_chemical_formula_weight         256.31
_chemical_name_systematic
;
9-Isopropenyl-4-methyl-2H-thieno[2,3-h]chromen-2-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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
_cell_angle_beta                 108.259(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.547(2)
_cell_length_b                   11.425(3)
_cell_length_c                   13.641(4)
_cell_measurement_reflns_used    812
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.1
_cell_volume                     1265.0(6)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.091
_diffrn_reflns_av_sigmaI/netI    0.080
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5816
_diffrn_reflns_theta_full        27.0
_diffrn_reflns_theta_max         27.0
_diffrn_reflns_theta_min         2.4
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.44
_refine_ls_extinction_coef       0.021(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.99
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2698
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.99
_refine_ls_R_factor_all          0.087
_refine_ls_R_factor_gt           0.068
_refine_ls_shift/esd_mean        0.000
_refine_ls_shift/su_max_lt       0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1022P)²P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.165
_refine_ls_wR_factor_ref         0.177
_reflns_number_gt                1870
_reflns_number_total             2698
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2449.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222164
_cod_database_fobs_code          2222164
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_disorder_assembly
_atom_site_disorder_group
S S1 0.97805(8) -0.09812(6) 0.19803(5) 0.0637(3) Uani d . 1 . .
O O1 0.65111(17) 0.10433(13) 0.38658(11) 0.0495(4) Uani d . 1 . .
O O2 0.4812(2) 0.18035(18) 0.46125(14) 0.0719(6) Uani d . 1 . .
C C1 0.6213(3) 0.1761(2) 0.45948(18) 0.0526(6) Uani d . 1 . .
C C2 0.7579(3) 0.2386(2) 0.52571(17) 0.0563(6) Uani d . 1 . .
H H2 0.7401 0.2892 0.5745 0.068 Uiso calc R 1 . .
C C3 0.9108(3) 0.22726(19) 0.52044(17) 0.0486(6) Uani d . 1 . .
C C4 0.9398(3) 0.14773(18) 0.44540(15) 0.0411(5) Uani d . 1 . .
C C5 1.0960(3) 0.12728(19) 0.43491(17) 0.0464(5) Uani d . 1 . .
H H5 1.1872 0.1650 0.4793 0.056 Uiso calc R 1 . .
C C6 1.1173(3) 0.0535(2) 0.36125(17) 0.0498(6) Uani d . 1 . .
H H6 1.2213 0.0407 0.3552 0.060 Uiso calc R 1 . .
C C7 0.9796(3) -0.0016(2) 0.29585(16) 0.0457(5) Uani d . 1 . .
C C8 0.8207(2) 0.01396(19) 0.30220(15) 0.0431(5) Uani d . 1 . .
C C9 0.8056(3) 0.09080(17) 0.37904(16) 0.0415(5) Uani d . 1 . .
C C10 0.6986(3) -0.0519(2) 0.22558(17) 0.0520(6) Uani d . 1 . .
C C11 0.7694(3) -0.1131(2) 0.1659(2) 0.0627(7) Uani d . 1 . .
H H11 0.7089 -0.1598 0.1114 0.075 Uiso calc R 1 . .
C C12 0.5195(3) -0.0597(2) 0.21115(19) 0.0587(7) Uani d . 1 . .
C C13 0.4143(4) -0.0004(4) 0.1349(3) 0.1030(12) Uani d . 1 . .
H H13A 0.3015 -0.0075 0.1233 0.124 Uiso calc R 1 . .
H H13B 0.4534 0.0484 0.0931 0.124 Uiso calc R 1 . .
C C14 0.4693(4) -0.1369(3) 0.2794(3) 0.0912(10) Uani d . 1 . .
H H14A 0.3512 -0.1377 0.2605 0.137 Uiso calc R 1 . .
H H14B 0.5147 -0.1099 0.3492 0.137 Uiso calc R 1 . .
H H14C 0.5084 -0.2146 0.2738 0.137 Uiso calc R 1 . .
C C15 1.0528(3) 0.2947(2) 0.5901(2) 0.0675(8) Uani d . 1 . .
H H15A 1.0157 0.3400 0.6378 0.101 Uiso calc R 1 . .
H H15B 1.0967 0.3460 0.5496 0.101 Uiso calc R 1 . .
H H15C 1.1369 0.2412 0.6277 0.101 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 S1 C7 . . 90.94(11) ?
C9 O1 C1 . . 121.72(17) ?
O2 C1 O1 . . 116.7(2) ?
O2 C1 C2 . . 126.1(2) ?
O1 C1 C2 . . 117.21(19) ?
C3 C2 C1 . . 122.6(2) ?
C3 C2 H2 . . 118.7 ?
C1 C2 H2 . . 118.7 ?
C2 C3 C4 . . 119.1(2) ?
C2 C3 C15 . . 121.8(2) ?
C4 C3 C15 . . 119.1(2) ?
C9 C4 C5 . . 118.38(19) ?
C9 C4 C3 . . 117.90(19) ?
C5 C4 C3 . . 123.7(2) ?
C6 C5 C4 . . 121.8(2) ?
C6 C5 H5 . . 119.1 ?
C4 C5 H5 . . 119.1 ?
C5 C6 C7 . . 118.1(2) ?
C5 C6 H6 . . 120.9 ?
C7 C6 H6 . . 120.9 ?
C6 C7 C8 . . 123.2(2) ?
C6 C7 S1 . . 125.92(17) ?
C8 C7 S1 . . 110.87(16) ?
C7 C8 C9 . . 116.35(19) ?
C7 C8 C10 . . 112.72(19) ?
C9 C8 C10 . . 130.9(2) ?
O1 C9 C4 . . 121.46(18) ?
O1 C9 C8 . . 116.39(18) ?
C4 C9 C8 . . 122.13(19) ?
C11 C10 C8 . . 110.4(2) ?
C11 C10 C12 . . 121.8(2) ?
C8 C10 C12 . . 127.7(2) ?
C10 C11 S1 . . 115.0(2) ?
C10 C11 H11 . . 122.5 ?
S1 C11 H11 . . 122.5 ?
C13 C12 C14 . . 123.5(3) ?
C13 C12 C10 . . 119.4(3) ?
C14 C12 C10 . . 117.0(2) ?
C12 C13 H13A . . 120.0 ?
C12 C13 H13B . . 120.0 ?
H13A C13 H13B . . 120.0 ?
C12 C14 H14A . . 109.5 ?
C12 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C12 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C3 C15 H15A . . 109.5 ?
C3 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C3 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
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 C11 . 1.706(3) ?
S1 C7 . 1.728(2) ?
O1 C9 . 1.365(2) ?
O1 C1 . 1.373(3) ?
O2 C1 . 1.205(3) ?
C1 C2 . 1.424(3) ?
C2 C3 . 1.338(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.447(3) ?
C3 C15 . 1.499(3) ?
C4 C9 . 1.381(3) ?
C4 C5 . 1.406(3) ?
C5 C6 . 1.367(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.385(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.399(3) ?
C8 C9 . 1.404(3) ?
C8 C10 . 1.437(3) ?
C10 C11 . 1.351(3) ?
C10 C12 . 1.484(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.328(4) ?
C12 C14 . 1.442(4) ?
C13 H13A . 0.9300 ?
C13 H13B . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
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
C11 H11 O2 2_645 0.93 2.44 3.293(3) 153
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742383
