#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/23/2012368.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_2012368
loop_
_publ_author_name
'Gzella, Andrzej'
'Rozwadowska, Maria D.'
'Sulima, Agnieszka'
_publ_section_title
;
Two dihydro-5H-thiazolinono[2,3-a]isoquinoline S-oxides
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica, Section C'
_journal_page_first              1454
_journal_page_last               1456
_journal_paper_doi               10.1107/S0108270101016638
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C13 H15 N O4 S'
_chemical_formula_moiety         'C13 H15 N O4 S'
_chemical_formula_sum            'C13 H15 N O4 S'
_chemical_formula_weight         281.32
_chemical_name_systematic
;
8,9-Dimethoxy-6,10b-dihydro-1-oxo-5H-thiazolo[2,3-a]isoquinolin-3-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                90.00
_cell_angle_beta                 102.967(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.967(2)
_cell_length_b                   7.5484(9)
_cell_length_c                   9.1666(13)
_cell_measurement_reflns_used    49
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      14.3
_cell_volume                     1346.3(3)
_computing_cell_refinement       'KM-4 Software'
_computing_data_collection       'KM-4 Software (Kuma, 1991)'
_computing_data_reduction        'KM-4 Software'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WINGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-7 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .996
_diffrn_measured_fraction_theta_max .996
_diffrn_measurement_device_type  'Kuma KM-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  .0437
_diffrn_reflns_av_sigmaI/netI    .0230
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2735
_diffrn_reflns_theta_full        70.17
_diffrn_reflns_theta_max         70.17
_diffrn_reflns_theta_min         2.27
_diffrn_standards_decay_%        3.5
_diffrn_standards_interval_count 100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    2.239
_exptl_absorpt_correction_T_max  .611
_exptl_absorpt_correction_T_min  .455
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          .50
_exptl_crystal_size_mid          .33
_exptl_crystal_size_min          .22
_refine_diff_density_max         .856
_refine_diff_density_min         -.330
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2556
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          .0641
_refine_ls_R_factor_gt           .0499
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1120P)²+0.4410P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .1464
_refine_ls_wR_factor_ref         .1583
_reflns_number_gt                2119
_reflns_number_total             2556
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn1001sup1.cif
_cod_data_source_block           IIa
_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.

'_exptl_absorpt_correction_type' value 'Psi-scan' changed to
'psi-scan' 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 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2012368
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_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 .13739(3) .30932(7) .08402(6) .0381(2) Uani d . 1 . . S
C2 .04978(12) .2658(3) -.0144(3) .0394(5) Uani d . 1 . . C
H2A .0199 .2591 .0556 .047 Uiso calc . 1 . . H
H2B .0333 .3595 -.0859 .047 Uiso calc . 1 . . H
C3 .05037(11) .0913(3) -.0942(2) .0372(5) Uani d . 1 . . C
N4 .10504(10) -.0061(2) -.0283(2) .0382(4) Uani d . 1 . . N
C5 .12147(14) -.1796(3) -.0795(3) .0486(6) Uani d . 1 . . C
H5A .0893 -.2090 -.1725 .058 Uiso calc . 1 . . H
H5B .1174 -.2685 -.0056 .058 Uiso calc . 1 . . H
C6 .19420(14) -.1792(3) -.1039(3) .0483(6) Uani d . 1 . . C
H6A .2074 -.2995 -.1221 .058 Uiso calc . 1 . . H
H6B .1956 -.1091 -.1918 .058 Uiso calc . 1 . . H
C6A .24505(12) -.1045(3) .0293(2) .0389(5) Uani d . 1 . . C
C7 .31396(13) -.1563(3) .0586(3) .0464(6) Uani d . 1 . . C
H7A .3281 -.2366 -.0053 .056 Uiso calc . 1 . . H
C8 .36166(12) -.0910(3) .1801(3) .0449(6) Uani d . 1 . . C
C9 .33926(12) .0297(3) .2768(2) .0400(5) Uani d . 1 . . C
C10 .27133(12) .0793(3) .2498(2) .0371(5) Uani d . 1 . . C
H10 .2569 .1576 .3149 .044 Uiso calc . 1 . . H
C10A .22341(11) .0135(3) .1255(2) .0336(5) Uani d . 1 . . C
C10B .14946(11) .0668(3) .1052(2) .0337(5) Uani d . 1 . . C
H10B .1329 .0278 .1928 .040 Uiso calc . 1 . . H
O1 .17430(10) .3703(3) -.0304(2) .0565(5) Uani d . 1 . . O
O2 .00588(9) .0465(2) -.20395(19) .0504(5) Uani d . 1 . . O
O3 .42959(10) -.1315(3) .2172(2) .0677(6) Uani d . 1 . . O
C11 .4545(2) -.2540(9) .1233(6) .129(2) Uani d . 1 . . C
H11A .4304 -.3644 .1213 .193 Uiso calc R 1 . . H
H11B .5028 -.2732 .1617 .193 Uiso calc R 1 . . H
H11C .4470 -.2069 .0236 .193 Uiso calc R 1 . . H
O4 .38964(9) .0877(3) .3936(2) .0575(5) Uani d . 1 . . O
C12 .3690(2) .2088(7) .4925(5) .1003(17) Uani d . 1 . . C
H12A .3535 .3165 .4399 .150 Uiso calc R 1 . . H
H12B .4073 .2341 .5741 .150 Uiso calc R 1 . . H
H12C .3323 .1582 .5308 .150 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 .0181 .0091 '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'
N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .3331 .5567 '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
O1 S1 C2 106.37(11) yes
O1 S1 C10B 107.90(10) yes
C2 S1 C10B 87.79(11) yes
C3 C2 S1 106.77(15) ?
C3 C2 H2A 110.4 ?
S1 C2 H2A 110.4 ?
C3 C2 H2B 110.4 ?
S1 C2 H2B 110.4 ?
H2A C2 H2B 108.6 ?
O2 C3 N4 125.6(2) ?
O2 C3 C2 123.6(2) ?
N4 C3 C2 110.75(19) ?
C3 N4 C10B 117.02(18) yes
C3 N4 C5 124.59(19) yes
C10B N4 C5 118.37(18) yes
N4 C5 C6 109.8(2) ?
N4 C5 H5A 109.7 ?
C6 C5 H5A 109.7 ?
N4 C5 H5B 109.7 ?
C6 C5 H5B 109.7 ?
H5A C5 H5B 108.2 ?
C6A C6 C5 111.9(2) ?
C6A C6 H6A 109.2 ?
C5 C6 H6A 109.2 ?
C6A C6 H6B 109.2 ?
C5 C6 H6B 109.2 ?
H6A C6 H6B 107.9 ?
C10A C6A C7 119.4(2) ?
C10A C6A C6 120.2(2) ?
C7 C6A C6 120.3(2) ?
C8 C7 C6A 121.7(2) ?
C8 C7 H7A 119.2 ?
C6A C7 H7A 119.2 ?
O3 C8 C7 126.2(2) ?
O3 C8 C9 115.3(2) ?
C7 C8 C9 118.5(2) ?
O4 C9 C10 125.2(2) ?
O4 C9 C8 114.7(2) ?
C10 C9 C8 120.1(2) ?
C9 C10 C10A 120.9(2) ?
C9 C10 H10 119.5 ?
C10A C10 H10 119.5 ?
C6A C10A C10 119.3(2) ?
C6A C10A C10B 122.1(2) ?
C10 C10A C10B 118.54(19) ?
N4 C10B C10A 113.67(17) ?
N4 C10B S1 104.24(14) ?
C10A C10B S1 112.28(15) ?
N4 C10B H10B 108.8 ?
C10A C10B H10B 108.8 ?
S1 C10B H10B 108.8 ?
C8 O3 C11 117.3(2) ?
O3 C11 H11A 109.5 ?
O3 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
O3 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
C9 O4 C12 116.2(2) ?
O4 C12 H12A 109.5 ?
O4 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
O4 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 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 O1 . 1.4836(18) yes
S1 C2 . 1.809(2) yes
S1 C10B . 1.851(2) yes
C2 C3 . 1.508(3) ?
C2 H2A . .9700 ?
C2 H2B . .9700 ?
C3 O2 . 1.231(3) yes
C3 N4 . 1.342(3) yes
N4 C10B . 1.449(3) yes
N4 C5 . 1.454(3) yes
C5 C6 . 1.518(4) ?
C5 H5A . .9700 ?
C5 H5B . .9700 ?
C6 C6A . 1.511(3) ?
C6 H6A . .9700 ?
C6 H6B . .9700 ?
C6A C10A . 1.389(3) ?
C6A C7 . 1.397(3) ?
C7 C8 . 1.384(3) ?
C7 H7A . .9300 ?
C8 O3 . 1.357(3) ?
C8 C9 . 1.412(3) ?
C9 O4 . 1.366(3) ?
C9 C10 . 1.375(3) ?
C10 C10A . 1.405(3) ?
C10 H10 . .9300 ?
C10A C10B . 1.501(3) ?
C10B H10B . .9800 ?
O3 C11 . 1.427(4) ?
C11 H11A . .9600 ?
C11 H11B . .9600 ?
C11 H11C . .9600 ?
O4 C12 . 1.413(4) ?
C12 H12A . .9600 ?
C12 H12B . .9600 ?
C12 H12C . .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
_geom_hbond_publ_flag
C2 H2B O2 2_554 .97 2.37 3.332(3) 169 yes
C10 H10 O1 4_566 .93 2.41 3.116(3) 132 yes
C11 H11B O4 2_645 .96 2.54 3.370(4) 144 yes
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
O1 S1 C2 C3 76.65(17)
C10B S1 C2 C3 -31.37(16)
S1 C2 C3 O2 -157.67(19)
S1 C2 C3 N4 22.9(2)
O2 C3 N4 C10B -176.6(2)
C2 C3 N4 C10B 2.8(3)
O2 C3 N4 C5 1.9(4)
C2 C3 N4 C5 -178.7(2)
C3 N4 C5 C6 125.4(2)
C10B N4 C5 C6 -56.1(3)
N4 C5 C6 C6A 49.7(3)
C5 C6 C6A C10A -25.3(3)
C5 C6 C6A C7 153.4(2)
C10A C6A C7 C8 -.9(4)
C6 C6A C7 C8 -179.6(2)
C6A C7 C8 O3 -179.3(3)
C6A C7 C8 C9 .5(4)
O3 C8 C9 O4 .0(3)
C7 C8 C9 O4 -179.9(2)
O3 C8 C9 C10 -179.8(2)
C7 C8 C9 C10 .4(4)
O4 C9 C10 C10A 179.4(2)
C8 C9 C10 C10A -.9(4)
C7 C6A C10A C10 .3(3)
C6 C6A C10A C10 179.1(2)
C7 C6A C10A C10B -176.6(2)
C6 C6A C10A C10B 2.1(3)
C9 C10 C10A C6A .5(3)
C9 C10 C10A C10B 177.6(2)
C3 N4 C10B C10A -148.8(2)
C5 N4 C10B C10A 32.6(3)
C3 N4 C10B S1 -26.3(2)
C5 N4 C10B S1 155.14(18)
C6A C10A C10B N4 -4.2(3)
C10 C10A C10B N4 178.81(18)
C6A C10A C10B S1 -122.2(2)
C10 C10A C10B S1 60.8(2)
O1 S1 C10B N4 -74.42(16)
C2 S1 C10B N4 32.08(14)
O1 S1 C10B C10A 49.07(17)
C2 S1 C10B C10A 155.56(16)
C7 C8 O3 C11 -.6(6)
C9 C8 O3 C11 179.6(4)
C10 C9 O4 C12 -.3(5)
C8 C9 O4 C12 179.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21135052
