#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/77/2007739.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_2007739
loop_
_publ_author_name
D.TranQui
'P. Fresneau'
M.Cussac
_publ_section_title
;
 (Z)-5-(2-Naphthylmethylene)-4-oxo-2-thioxo-1,3-thiazolidine-3-acetic
 Acid Dimethyl Sulfoxide Solvate
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1501
_journal_page_last               1503
_journal_paper_doi               10.1107/S0108270198004600
_journal_volume                  54
_journal_year                    1998
_chemical_formula_iupac          'C16 H11 N O3 S2 , C2 H6 O S'
_chemical_formula_sum            'C18 H17 N O4 S3'
_chemical_formula_weight         407.51
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                81.23(5)
_cell_angle_beta                 98.52(5)
_cell_angle_gamma                104.46(5)
_cell_formula_units_Z            2
_cell_length_a                   7.320(5)
_cell_length_b                   8.307(5)
_cell_length_c                   16.399(5)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.2
_cell_measurement_theta_min      8.4
_cell_volume                     948.0(9)
_computing_cell_refinement       SDP
_computing_data_collection       'SDP (B. A. Frenz & Associates, 1979)'
_computing_data_reduction        SDP
_computing_molecular_graphics    'Xtal\_GX (Hall & du Boulay, 1995)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       '2θ/ω scan'
_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  0.047
_diffrn_reflns_av_sigmaI/netI    0.0111
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5099
_diffrn_reflns_theta_max         22.97
_diffrn_reflns_theta_min         1.26
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  '90 min'
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            transparent
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         .248
_refine_diff_density_min         -.223
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.974
_refine_ls_goodness_of_fit_obs   0.897
_refine_ls_hydrogen_treatment    'H atoms: see text'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         2481
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.112
_refine_ls_restrained_S_obs      0.901
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_obs          0.0437
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0570P)²+1.0892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1370
_refine_ls_wR_factor_obs         0.1000
_reflns_number_observed          2122
_reflns_number_total             2549
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            mu1359.cif
_cod_data_source_block           custo
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0570P)^2^+1.0892P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0570P)^2^+1.0892P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        947.9(9)
_cod_database_code               2007739
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
S1 0.68460(12) 0.93961(10) 0.39515(5) 0.0596(3) Uani d D 1 . S
S2 0.6050(2) 1.23100(12) 0.27806(7) 0.0871(4) Uani d . 1 . S
O1 0.5331(3) 0.6438(3) 0.22698(13) 0.0614(6) Uani d . 1 . O
O2 0.6271(4) 1.1524(3) 0.0440(2) 0.0863(8) Uani d . 1 . O
H2 0.686(5) 1.2489(9) 0.0496(10) 0.092(3) Uiso calc R 1 . H
O3 0.8243(4) 1.0388(4) 0.1366(2) 0.1049(10) Uani d . 1 . O
N1 0.5560(3) 0.9183(3) 0.24363(13) 0.0490(6) Uani d D 1 . N
C1 0.6109(5) 1.0365(4) 0.2976(2) 0.0573(8) Uani d D 1 . C
C2 0.5729(4) 0.7562(3) 0.2708(2) 0.0465(7) Uani d D 1 . C
C3 0.6470(4) 0.7425(3) 0.3609(2) 0.0431(6) Uani d D 1 . C
C4 0.4955(5) 0.9698(4) 0.1554(2) 0.0610(8) Uani d D 1 . C
H4A 0.4135(5) 1.0467(4) 0.1517(2) 0.075(7) Uiso calc R 1 . H
H4B 0.4243(5) 0.8723(4) 0.1291(2) 0.075(7) Uiso calc R 1 . H
C5 0.6659(6) 1.0529(4) 0.1113(2) 0.0620(9) Uani d . 1 . C
C6 0.6742(4) 0.5979(3) 0.4024(2) 0.0450(7) Uani d . 1 . C
H6 0.6440(4) 0.5104(3) 0.3699(2) 0.092(3) Uiso calc R 1 . H
C7 0.7409(4) 0.5504(4) 0.4871(2) 0.0478(7) Uani d D 1 . C
C8 0.7922(5) 0.6607(4) 0.5482(2) 0.0646(9) Uani d D 1 . C
H8 0.7849(5) 0.7719(4) 0.5345(2) 0.092(3) Uiso calc R 1 . H
C9 0.8535(5) 0.6034(4) 0.6285(2) 0.0621(9) Uani d D 1 . C
H9 0.8867(5) 0.6781(4) 0.6681(2) 0.092(3) Uiso calc R 1 . H
C10 0.8681(4) 0.4373(4) 0.6532(2) 0.0566(8) Uani d D 1 . C
C11 0.9259(5) 0.3748(4) 0.7345(2) 0.0583(8) Uani d D 1 . C
H11 0.9590(5) 0.4477(4) 0.7748(2) 0.092(3) Uiso calc R 1 . H
C12 0.9362(5) 0.2099(4) 0.7578(2) 0.0667(9) Uani d D 1 . C
H12 0.9738(5) 0.1721(4) 0.8126(2) 0.092(3) Uiso calc R 1 . H
C13 0.8878(4) 0.1008(4) 0.6960(2) 0.0634(9) Uani d D 1 . C
H13 0.8948(4) -0.0106(4) 0.7094(2) 0.092(3) Uiso calc R 1 . H
C14 0.8295(5) 0.1609(4) 0.6148(2) 0.0585(8) Uani d D 1 . C
H14 0.7974(5) 0.0871(4) 0.5748(2) 0.092(3) Uiso calc R 1 . H
C15 0.8170(4) 0.3273(4) 0.5906(2) 0.0492(7) Uani d D 1 . C
C16 0.7542(4) 0.3854(4) 0.5101(2) 0.0508(7) Uani d D 1 . C
H16 0.7198(4) 0.3115(4) 0.4702(2) 0.092(3) Uiso calc R 1 . H
S3 -1.1216(2) -1.24364(13) 0.98958(6) 0.0830(3) Uani d . 1 . S
O4 -0.9284(4) -1.2808(4) 1.0260(2) 0.0920(8) Uani d . 1 . O
C17 -1.1935(6) -1.3540(5) 0.9008(2) 0.0877(12) Uani d . 1 . C
H17A -1.3140(17) -1.336(2) 0.8746(9) 0.092(3) Uiso calc R 1 . H
H17B -1.205(3) -1.4716(6) 0.9177(3) 0.092(3) Uiso calc R 1 . H
H17C -1.1005(17) -1.315(2) 0.8624(7) 0.092(3) Uiso calc R 1 . H
C18 -1.2800(6) -1.3764(6) 1.0570(3) 0.105(2) Uani d . 1 . C
H18A -1.4081(7) -1.372(2) 1.0356(8) 0.092(3) Uiso calc R 1 . H
H18B -1.251(2) -1.3399(19) 1.1112(5) 0.092(3) Uiso calc R 1 . H
H18C -1.267(2) -1.4893(8) 1.0606(12) 0.092(3) Uiso calc R 1 . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 '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_3
_geom_angle
_geom_angle_publ_flag
C1 S1 C3 . 94.03(14) y
C5 O2 H2 . 109.5(2) y
C1 N1 C2 . 119.5(2) y
C1 N1 C4 . 119.2(2) y
C2 N1 C4 . 121.1(2) y
N1 C1 S2 . 127.2(2) y
N1 C1 S1 . 108.4(2) y
S2 C1 S1 . 124.4(2) y
O1 C2 N1 . 124.3(3) y
O1 C2 C3 . 126.2(3) y
N1 C2 C3 . 109.6(2) y
C6 C3 C2 . 121.4(2) y
C6 C3 S1 . 130.1(2) y
C2 C3 S1 . 108.5(2) y
N1 C4 C5 . 109.9(3) y
N1 C4 H4A . 109.7(2) ?
C5 C4 H4A . 109.7(2) ?
N1 C4 H4B . 109.7(2) ?
C5 C4 H4B . 109.7(2) ?
H4A C4 H4B . 108.2 ?
O3 C5 O2 . 122.7(4) y
O3 C5 C4 . 124.1(3) y
O2 C5 C4 . 113.1(3) y
C3 C6 C7 . 132.8(3) y
C3 C6 H6 . 113.6(2) ?
C7 C6 H6 . 113.6(2) ?
C16 C7 C8 . 118.3(3) y
C16 C7 C6 . 117.8(2) y
C8 C7 C6 . 123.8(3) y
C9 C8 C7 . 119.8(3) y
C9 C8 H8 . 120.1(2) ?
C7 C8 H8 . 120.1(2) ?
C8 C9 C10 . 122.9(3) y
C8 C9 H9 . 118.6(2) ?
C10 C9 H9 . 118.6(2) ?
C11 C10 C9 . 124.1(3) y
C11 C10 C15 . 119.1(3) y
C9 C10 C15 . 116.7(3) y
C12 C11 C10 . 123.2(3) y
C12 C11 H11 . 118.4(2) ?
C10 C11 H11 . 118.4(2) ?
C11 C12 C13 . 117.9(3) y
C11 C12 H12 . 121.0(2) ?
C13 C12 H12 . 121.0(2) ?
C14 C13 C12 . 119.6(3) y
C14 C13 H13 . 120.2(2) ?
C12 C13 H13 . 120.2(2) ?
C13 C14 C15 . 122.9(3) y
C13 C14 H14 . 118.5(2) ?
C15 C14 H14 . 118.5(2) ?
C16 C15 C14 . 122.8(3) y
C16 C15 C10 . 120.1(3) y
C14 C15 C10 . 117.1(3) y
C15 C16 C7 . 122.2(3) y
C15 C16 H16 . 118.9(2) ?
C7 C16 H16 . 118.9(2) ?
O4 S3 C17 . 105.0(2) y
O4 S3 C18 . 103.1(2) y
C17 S3 C18 . 98.6(2) y
S3 O4 O2 2_556 122.2(2) ?
S3 C17 H17A . 109.5(2) ?
S3 C17 H17B . 109.47(14) ?
H17A C17 H17B . 109.5 ?
S3 C17 H17C . 109.5(2) ?
H17A C17 H17C . 109.5 ?
H17B C17 H17C . 109.5 ?
S3 C18 H18A . 109.5(2) ?
S3 C18 H18B . 109.47(14) ?
H18A C18 H18B . 109.5 ?
S3 C18 H18C . 109.5(2) ?
H18A C18 H18C . 109.5 ?
H18B C18 H18C . 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 C1 . 1.751(3) y
S1 C3 . 1.755(3) y
S2 C1 . 1.609(3) y
O1 C2 . 1.217(3) y
O2 C5 . 1.315(4) y
O2 H2 . 0.82 ?
O3 C5 . 1.200(4) y
N1 C1 . 1.368(3) y
N1 C2 . 1.382(3) y
N1 C4 . 1.480(3) y
C2 C3 . 1.494(4) y
C3 C6 . 1.332(4) y
C4 C5 . 1.496(5) y
C4 H4A . 0.97 ?
C4 H4B . 0.97 ?
C6 C7 . 1.433(4) y
C6 H6 . 0.93 ?
C7 C16 . 1.388(4) y
C7 C8 . 1.407(4) y
C8 C9 . 1.379(4) y
C8 H8 . 0.93 ?
C9 C10 . 1.403(4) y
C9 H9 . 0.93 ?
C10 C11 . 1.399(4) y
C10 C15 . 1.426(4) y
C11 C12 . 1.383(4) y
C11 H11 . 0.93 ?
C12 C13 . 1.409(4) y
C12 H12 . 0.93 ?
C13 C14 . 1.394(4) y
C13 H13 . 0.93 ?
C14 C15 . 1.400(4) y
C14 H14 . 0.93 ?
C15 C16 . 1.387(4) y
C16 H16 . 0.93 ?
S3 O4 . 1.538(3) y
S3 C17 . 1.782(4) y
S3 C18 . 1.775(5) y
O4 O2 2_556 2.554(5) y
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
