#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/18/2201854.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_2201854
loop_
_publ_author_name
'Li, Xiao-Fang'
'Feng, Ya-Qing'
'Gu, Yun-Feng'
_publ_section_title
3-(2,6-Dichlorophenyl)-8-ethyl-4-phenyl-1-oxa-6-thia-2,8-diazaspiro[4.4]non-2-ene-7,9-dione
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o330
_journal_page_last               o331
_journal_paper_doi               10.1107/S1600536803003003
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C19 H14 Cl2 N2 O3 S'
_chemical_formula_moiety         'C19 H14 Cl2 N2 O3 S'
_chemical_formula_sum            'C19 H14 Cl2 N2 O3 S'
_chemical_formula_weight         421.28
_chemical_name_systematic
;
3-(2,6-Dichlorophenyl)-8-ethyl-4-phenyl-1-oxa-6-thia-2,8-diazaspiro[4.4]non-
2-ene-7,9-dione
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.0339(9)
_cell_length_b                   12.5618(12)
_cell_length_c                   30.220(3)
_cell_measurement_reflns_used    864
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.21
_cell_measurement_theta_min      2.68
_cell_volume                     3809.0(6)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 1998)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0569
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            13516
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.35
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.473
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_correction_T_min  0.825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.332
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3335
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0520
_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)+(0.084P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1104
_reflns_number_gt                2148
_reflns_number_total             3335
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf6237.cif
_cod_data_source_block           I
_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_enum 1527 2010-12-29 10:47:43Z saulius 

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        3809.1(7)
_cod_database_code               2201854
_cod_database_fobs_code          2201854
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_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
_atom_site_type_symbol
S1 0.12407(10) 0.47626(8) 0.46069(3) 0.0582(3) Uani d . 1 . . S
Cl1 0.28598(11) 0.33697(8) 0.27374(3) 0.0688(3) Uani d . 1 . . Cl
Cl2 -0.03391(12) 0.67094(8) 0.31535(4) 0.0833(4) Uani d . 1 . . Cl
N1 0.3347(3) 0.3573(2) 0.47022(9) 0.0514(8) Uani d . 1 . . N
N2 0.2437(3) 0.5770(3) 0.35317(9) 0.0605(9) Uani d . 1 . . N
O1 0.2129(3) 0.3869(2) 0.53316(9) 0.0770(9) Uani d . 1 . . O
O2 0.4271(3) 0.3571(3) 0.40150(10) 0.1123(14) Uani d . 1 . . O
O3 0.2809(3) 0.5541(2) 0.39765(8) 0.0750(9) Uani d . 1 . . O
C1 0.2306(4) 0.4008(3) 0.49435(12) 0.0517(9) Uani d . 1 . . C
C2 0.3407(4) 0.3839(3) 0.42664(13) 0.0613(11) Uani d . 1 . . C
C3 0.2243(3) 0.4544(3) 0.41168(11) 0.0475(9) Uani d . 1 . . C
C4 0.1537(3) 0.4089(3) 0.37016(10) 0.0393(8) Uani d . 1 . . C
H4 0.2056 0.3479 0.3596 0.047 Uiso calc R 1 . . H
C5 0.1750(3) 0.5004(3) 0.33819(10) 0.0406(8) Uani d . 1 . . C
C6 0.4353(4) 0.2884(3) 0.49189(14) 0.0671(11) Uani d . 1 . . C
H6A 0.4712 0.2390 0.4703 0.081 Uiso calc R 1 . . H
H6B 0.3927 0.2473 0.5151 0.081 Uiso calc R 1 . . H
C7 0.5473(4) 0.3527(3) 0.51148(15) 0.0803(14) Uani d . 1 . . C
H7A 0.5924 0.3908 0.4884 0.120 Uiso calc R 1 . . H
H7B 0.6091 0.3059 0.5260 0.120 Uiso calc R 1 . . H
H7C 0.5119 0.4024 0.5326 0.120 Uiso calc R 1 . . H
C8 0.0103(3) 0.3735(3) 0.37547(10) 0.0379(8) Uani d . 1 . . C
C9 -0.0200(4) 0.2668(3) 0.37114(11) 0.0507(9) Uani d . 1 . . C
H9 0.0462 0.2183 0.3636 0.061 Uiso calc R 1 . . H
C10 -0.1499(4) 0.2321(3) 0.37810(13) 0.0650(11) Uani d . 1 . . C
H10 -0.1704 0.1603 0.3749 0.078 Uiso calc R 1 . . H
C11 -0.2473(4) 0.3023(3) 0.38958(12) 0.0561(10) Uani d . 1 . . C
H11 -0.3336 0.2782 0.3946 0.067 Uiso calc R 1 . . H
C12 -0.2186(4) 0.4074(3) 0.39364(11) 0.0527(9) Uani d . 1 . . C
H12 -0.2853 0.4554 0.4013 0.063 Uiso calc R 1 . . H
C13 -0.0900(3) 0.4432(3) 0.38640(11) 0.0476(9) Uani d . 1 . . C
H13 -0.0712 0.5155 0.3890 0.057 Uiso calc R 1 . . H
C14 0.1258(3) 0.5055(2) 0.29201(10) 0.0404(8) Uani d . 1 . . C
C15 0.1724(3) 0.4356(3) 0.25966(11) 0.0461(9) Uani d . 1 . . C
C16 0.1335(4) 0.4427(3) 0.21599(12) 0.0610(11) Uani d . 1 . . C
H16 0.1682 0.3960 0.1951 0.073 Uiso calc R 1 . . H
C17 0.0437(5) 0.5187(4) 0.20362(14) 0.0740(12) Uani d . 1 . . C
H17 0.0168 0.5232 0.1742 0.089 Uiso calc R 1 . . H
C18 -0.0071(4) 0.5883(4) 0.23403(14) 0.0692(12) Uani d . 1 . . C
H18 -0.0688 0.6395 0.2254 0.083 Uiso calc R 1 . . H
C19 0.0340(4) 0.5823(3) 0.27798(12) 0.0528(10) Uani d . 1 . . C
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'
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'
Cl Cl 0.1484 0.1585 '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_publ_flag
C1 S1 C3 93.10(17) y
C2 N1 C1 116.5(3) y
C2 N1 C6 122.8(3) ?
C1 N1 C6 120.7(3) ?
C5 N2 O3 109.0(3) y
N2 O3 C3 110.5(2) y
O1 C1 N1 124.7(4) ?
O1 C1 S1 123.8(3) ?
N1 C1 S1 111.5(3) y
O2 C2 N1 125.1(4) ?
O2 C2 C3 121.7(4) ?
N1 C2 C3 113.2(3) y
O3 C3 C2 106.7(3) ?
O3 C3 C4 105.2(3) y
C2 C3 C4 112.0(3) ?
O3 C3 S1 109.1(2) ?
C2 C3 S1 105.6(2) y
C4 C3 S1 117.7(2) ?
C8 C4 C5 115.1(3) ?
C8 C4 C3 117.2(3) ?
C5 C4 C3 99.9(3) ?
C8 C4 H4 108.0 ?
C5 C4 H4 108.0 ?
C3 C4 H4 108.0 ?
N2 C5 C14 119.0(3) ?
N2 C5 C4 115.1(3) ?
C14 C5 C4 125.9(3) ?
N1 C6 C7 111.7(3) ?
N1 C6 H6A 109.3 ?
C7 C6 H6A 109.3 ?
N1 C6 H6B 109.3 ?
C7 C6 H6B 109.3 ?
H6A C6 H6B 107.9 ?
C6 C7 H7A 109.5 ?
C6 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
C6 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
C13 C8 C9 118.7(3) ?
C13 C8 C4 122.3(3) ?
C9 C8 C4 119.0(3) ?
C8 C9 C10 119.8(3) ?
C8 C9 H9 120.1 ?
C10 C9 H9 120.1 ?
C11 C10 C9 120.6(4) ?
C11 C10 H10 119.7 ?
C9 C10 H10 119.7 ?
C12 C11 C10 120.0(4) ?
C12 C11 H11 120.0 ?
C10 C11 H11 120.0 ?
C11 C12 C13 120.0(3) ?
C11 C12 H12 120.0 ?
C13 C12 H12 120.0 ?
C8 C13 C12 120.9(3) ?
C8 C13 H13 119.5 ?
C12 C13 H13 119.5 ?
C15 C14 C19 116.2(3) ?
C15 C14 C5 121.4(3) ?
C19 C14 C5 122.4(3) ?
C16 C15 C14 122.4(3) ?
C16 C15 Cl1 117.8(3) ?
C14 C15 Cl1 119.8(3) ?
C17 C16 C15 119.6(4) ?
C17 C16 H16 120.2 ?
C15 C16 H16 120.2 ?
C16 C17 C18 120.6(4) ?
C16 C17 H17 119.7 ?
C18 C17 H17 119.7 ?
C17 C18 C19 119.7(4) ?
C17 C18 H18 120.1 ?
C19 C18 H18 120.1 ?
C18 C19 C14 121.4(4) ?
C18 C19 Cl2 118.2(3) ?
C14 C19 Cl2 120.4(3) ?
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 . 1.754(4) y
S1 C3 . 1.811(3) y
Cl1 C15 . 1.737(4) y
Cl2 C19 . 1.726(4) y
N1 C2 . 1.360(5) y
N1 C1 . 1.387(4) y
N1 C6 . 1.481(4) y
N2 C5 . 1.268(4) y
N2 O3 . 1.425(4) y
O1 C1 . 1.199(4) ?
O2 C2 . 1.201(4) ?
O3 C3 . 1.440(4) y
C2 C3 . 1.534(5) ?
C3 C4 . 1.550(4) ?
C4 C8 . 1.514(4) ?
C4 C5 . 1.516(4) ?
C4 H4 . 0.980 ?
C5 C14 . 1.482(4) ?
C6 C7 . 1.505(5) ?
C6 H6A . 0.970 ?
C6 H6B . 0.970 ?
C7 H7A . 0.960 ?
C7 H7B . 0.960 ?
C7 H7C . 0.960 ?
C8 C13 . 1.374(4) ?
C8 C9 . 1.381(4) ?
C9 C10 . 1.390(5) ?
C9 H9 . 0.930 ?
C10 C11 . 1.361(5) ?
C10 H10 . 0.930 ?
C11 C12 . 1.357(5) ?
C11 H11 . 0.930 ?
C12 C13 . 1.384(5) ?
C12 H12 . 0.930 ?
C13 H13 . 0.930 ?
C14 C15 . 1.395(4) ?
C14 C19 . 1.399(5) ?
C15 C16 . 1.379(5) ?
C16 C17 . 1.365(6) ?
C16 H16 . 0.930 ?
C17 C18 . 1.367(6) ?
C17 H17 . 0.930 ?
C18 C19 . 1.393(5) ?
C18 H18 . 0.930 ?
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
C5 N2 O3 C3 -2.5(4)
C2 N1 C1 O1 -178.5(4)
C6 N1 C1 O1 -0.3(5)
C2 N1 C1 S1 3.2(4)
C6 N1 C1 S1 -178.7(3)
C3 S1 C1 O1 179.6(3)
C3 S1 C1 N1 -2.0(3)
C1 N1 C2 O2 176.7(4)
C6 N1 C2 O2 -1.4(6)
C1 N1 C2 C3 -2.9(5)
C6 N1 C2 C3 179.1(3)
N2 O3 C3 C2 123.4(3)
N2 O3 C3 C4 4.3(4)
N2 O3 C3 S1 -122.9(3)
O2 C2 C3 O3 -62.3(5)
N1 C2 C3 O3 117.3(3)
O2 C2 C3 C4 52.4(5)
N1 C2 C3 C4 -128.1(3)
O2 C2 C3 S1 -178.4(4)
N1 C2 C3 S1 1.2(4)
C1 S1 C3 O3 -114.0(2)
C1 S1 C3 C2 0.5(3)
C1 S1 C3 C4 126.3(3)
O3 C3 C4 C8 -129.1(3)
C2 C3 C4 C8 115.3(3)
S1 C3 C4 C8 -7.4(4)
O3 C3 C4 C5 -4.2(3)
C2 C3 C4 C5 -119.7(3)
S1 C3 C4 C5 117.6(3)
O3 N2 C5 C14 -179.3(3)
O3 N2 C5 C4 -0.6(4)
C8 C4 C5 N2 129.5(3)
C3 C4 C5 N2 3.1(4)
C8 C4 C5 C14 -51.9(4)
C3 C4 C5 C14 -178.3(3)
C2 N1 C6 C7 91.1(4)
C1 N1 C6 C7 -86.8(4)
C5 C4 C8 C13 -53.7(4)
C3 C4 C8 C13 63.2(4)
C5 C4 C8 C9 129.2(3)
C3 C4 C8 C9 -113.8(3)
C13 C8 C9 C10 -0.4(5)
C4 C8 C9 C10 176.8(3)
C8 C9 C10 C11 -0.6(6)
C9 C10 C11 C12 1.0(6)
C10 C11 C12 C13 -0.4(6)
C9 C8 C13 C12 1.0(5)
C4 C8 C13 C12 -176.0(3)
C11 C12 C13 C8 -0.6(5)
N2 C5 C14 C15 113.2(4)
C4 C5 C14 C15 -65.4(4)
N2 C5 C14 C19 -64.6(4)
C4 C5 C14 C19 116.8(4)
C19 C14 C15 C16 1.6(5)
C5 C14 C15 C16 -176.4(3)
C19 C14 C15 Cl1 -179.7(2)
C5 C14 C15 Cl1 2.4(4)
C14 C15 C16 C17 -1.6(6)
Cl1 C15 C16 C17 179.6(3)
C15 C16 C17 C18 0.5(6)
C16 C17 C18 C19 0.5(6)
C17 C18 C19 C14 -0.6(6)
C17 C18 C19 Cl2 -179.4(3)
C15 C14 C19 C18 -0.4(5)
C5 C14 C19 C18 177.5(3)
C15 C14 C19 Cl2 178.3(2)
C5 C14 C19 Cl2 -3.8(4)
