#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:26:14 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178469 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/90/4029045.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_4029045
loop_
_publ_author_name
'Paladhi, Sushovan'
'Bhati, Meeta'
'Panda, Deepanjan'
'Dash, Jyotirmayee'
_publ_section_title
;
 Thiazolidinedione-Isatin Conjugates via an Uncatalyzed Diastereoselective
 Aldol Reaction on Water.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1473
_journal_paper_doi               10.1021/jo402515d
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C14 H14 N2 O4 S'
_chemical_formula_sum            'C14 H14 N2 O4 S'
_chemical_formula_weight         306.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 103.439(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3514(9)
_cell_length_b                   7.3471(5)
_cell_length_c                   14.3492(9)
_cell_measurement_reflns_used    7947
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.61
_cell_measurement_theta_min      2.92
_cell_volume                     1369.03(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11824
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, Bruker 2008'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2994
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0287
_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)+(0.0323P)²+0.8308P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0755
_reflns_number_gt                2699
_reflns_number_total             2994
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402515d_si_001.cif
_cod_data_source_block           3ba
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4029045
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.90090(2) 0.42973(4) 0.07177(2) 0.01181(9) Uani 1 1 d .
O1 O 0.87003(7) 0.03609(12) -0.11139(6) 0.01244(19) Uani 1 1 d .
O2 O 0.81410(8) 0.64107(13) -0.07443(7) 0.0196(2) Uani 1 1 d .
O3 O 0.68749(7) 0.08330(14) -0.00133(7) 0.0182(2) Uani 1 1 d .
O4 O 0.88464(7) -0.12057(12) 0.08022(6) 0.01222(19) Uani 1 1 d .
H4 H 0.8571 -0.1449 0.0244 0.018 Uiso 1 1 calc R
N1 N 0.83314(8) 0.33932(14) -0.10769(7) 0.0110(2) Uani 1 1 d .
C14 C 0.61331(10) 0.1455(2) 0.17158(10) 0.0187(3) Uani 1 1 d .
H2A H 0.5671 0.1296 0.1100 0.028 Uiso 1 1 calc R
H2B H 0.6040 0.2646 0.1957 0.028 Uiso 1 1 calc R
H2C H 0.5991 0.0552 0.2151 0.028 Uiso 1 1 calc R
C5 C 0.86900(11) 0.3891(2) -0.26756(9) 0.0189(3) Uani 1 1 d .
H1A H 0.9045 0.5007 -0.2466 0.028 Uiso 1 1 calc R
H1B H 0.8366 0.3976 -0.3346 0.028 Uiso 1 1 calc R
H1C H 0.9173 0.2901 -0.2573 0.028 Uiso 1 1 calc R
C4 C 0.78764(10) 0.35560(17) -0.21110(8) 0.0128(2) Uani 1 1 d .
H2D H 0.7387 0.4553 -0.2221 0.015 Uiso 1 1 calc R
H2E H 0.7505 0.2447 -0.2338 0.015 Uiso 1 1 calc R
C2 C 0.87120(9) 0.17639(17) -0.06674(8) 0.0100(2) Uani 1 1 d .
C3 C 0.91598(9) 0.19362(16) 0.04066(8) 0.0100(2) Uani 1 1 d .
H4A H 0.9896 0.1651 0.0540 0.012 Uiso 1 1 calc R
C7 C 0.86375(9) 0.06320(17) 0.09935(8) 0.0103(2) Uani 1 1 d .
C13 C 0.89537(10) 0.09943(17) 0.20559(8) 0.0113(2) Uani 1 1 d .
C12 C 0.80675(10) 0.13217(17) 0.23921(9) 0.0126(2) Uani 1 1 d .
C11 C 0.81126(11) 0.16714(18) 0.33483(9) 0.0171(3) Uani 1 1 d .
H8 H 0.7519 0.1872 0.3568 0.021 Uiso 1 1 calc R
C10 C 0.90881(11) 0.17102(19) 0.39688(9) 0.0200(3) Uani 1 1 d .
H9 H 0.9143 0.1935 0.4617 0.024 Uiso 1 1 calc R
C1 C 0.84218(9) 0.48911(18) -0.04815(9) 0.0125(2) Uani 1 1 d .
C6 C 0.74530(9) 0.09369(17) 0.07774(9) 0.0124(2) Uani 1 1 d .
N2 N 0.71885(8) 0.12580(15) 0.16233(8) 0.0133(2) Uani 1 1 d .
C9 C 0.99794(11) 0.14217(19) 0.36438(10) 0.0193(3) Uani 1 1 d .
H13 H 1.0619 0.1473 0.4072 0.023 Uiso 1 1 calc R
C8 C 0.99154(10) 0.10543(18) 0.26746(9) 0.0145(3) Uani 1 1 d .
H14 H 1.0507 0.0855 0.2452 0.017 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 S1 C3 92.63(6)
C7 O4 H4 109.5
C2 N1 C1 117.26(10)
C2 N1 C4 121.70(10)
C1 N1 C4 121.00(10)
N2 C14 H2A 109.5
N2 C14 H2B 109.5
H2A C14 H2B 109.5
N2 C14 H2C 109.5
H2A C14 H2C 109.5
H2B C14 H2C 109.5
C4 C5 H1A 109.5
C4 C5 H1B 109.5
H1A C5 H1B 109.5
C4 C5 H1C 109.5
H1A C5 H1C 109.5
H1B C5 H1C 109.5
N1 C4 C5 111.86(10)
N1 C4 H2D 109.2
C5 C4 H2D 109.2
N1 C4 H2E 109.2
C5 C4 H2E 109.2
H2D C4 H2E 107.9
O1 C2 N1 123.74(11)
O1 C2 C3 124.02(11)
N1 C2 C3 112.24(10)
C2 C3 C7 112.29(10)
C2 C3 S1 106.77(8)
C7 C3 S1 111.66(8)
C2 C3 H4A 108.7
C7 C3 H4A 108.7
S1 C3 H4A 108.7
O4 C7 C13 110.01(10)
O4 C7 C3 110.55(9)
C13 C7 C3 112.69(10)
O4 C7 C6 109.58(10)
C13 C7 C6 102.06(9)
C3 C7 C6 111.65(10)
C8 C13 C12 120.48(11)
C8 C13 C7 130.94(11)
C12 C13 C7 108.58(11)
C11 C12 C13 121.92(12)
C11 C12 N2 128.14(12)
C13 C12 N2 109.93(11)
C12 C11 C10 117.07(12)
C12 C11 H8 121.5
C10 C11 H8 121.5
C9 C10 C11 121.78(12)
C9 C10 H9 119.1
C11 C10 H9 119.1
O2 C1 N1 124.50(11)
O2 C1 S1 124.41(10)
N1 C1 S1 111.09(9)
O3 C6 N2 127.04(12)
O3 C6 C7 124.87(11)
N2 C6 C7 108.04(10)
C6 N2 C12 111.20(10)
C6 N2 C14 123.83(11)
C12 N2 C14 124.94(10)
C10 C9 C8 120.19(13)
C10 C9 H13 119.9
C8 C9 H13 119.9
C13 C8 C9 118.53(12)
C13 C8 H14 120.7
C9 C8 H14 120.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.7716(13)
S1 C3 1.8140(12)
O1 C2 1.2119(15)
O2 C1 1.2098(16)
O3 C6 1.2173(16)
O4 C7 1.4184(15)
O4 H4 0.8200
N1 C2 1.3775(16)
N1 C1 1.3811(16)
N1 C4 1.4718(15)
C14 N2 1.4531(16)
C14 H2A 0.9600
C14 H2B 0.9600
C14 H2C 0.9600
C5 C4 1.5185(17)
C5 H1A 0.9600
C5 H1B 0.9600
C5 H1C 0.9600
C4 H2D 0.9700
C4 H2E 0.9700
C2 C3 1.5232(16)
C3 C7 1.5448(16)
C3 H4A 0.9800
C7 C13 1.5080(16)
C7 C6 1.5555(17)
C13 C8 1.3816(18)
C13 C12 1.3985(17)
C12 C11 1.3835(18)
C12 N2 1.4123(16)
C11 C10 1.397(2)
C11 H8 0.9300
C10 C9 1.392(2)
C10 H9 0.9300
C6 N2 1.3612(16)
C9 C8 1.3996(18)
C9 H13 0.9300
C8 H14 0.9300
