#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/77/2227720.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_2227720
loop_
_publ_author_name
'Navarrete-Vázquez, Gabriel'
'Morales-Vilchis, Guadalupe'
'Estrada-Soto, Samuel'
'Rodríguez-López, Verónica'
'Tlahuext, Hugo'
_publ_section_title
;
 Ethyl
 2-{(2Z)-2-[(1-naphthylsulfonyl)imino]-2,3-dihydro-1,3-thiazol-4-yl}acetate
 monohydrate
;
_journal_coeditor_code           JH2215
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2744
_journal_paper_doi               10.1107/S1600536810039279
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H16 N2 O4 S2, H2 O'
_chemical_formula_moiety         'C17 H16 N2 O4 S2, H2 O'
_chemical_formula_sum            'C17 H18 N2 O5 S2'
_chemical_formula_weight         394.45
_chemical_melting_point          371
_chemical_name_systematic
;
Ethyl 2-{(2Z)-2-[(1-naphthylsulfonyl)imino]-2,3-dihydro-
1,3-thiazol-4-yl}acetate monohydrate
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.582(6)
_cell_length_b                   7.9657(17)
_cell_length_c                   15.676(3)
_cell_measurement_reflns_used    7399
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      23.63
_cell_measurement_theta_min      2.60
_cell_volume                     3693.9(13)
_computing_cell_refinement       'SAINT-Plus-NT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT-Plus-NT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL-NT (Sheldrick, 2008)'
_computing_publication_material
;
PLATON (Spek, 2009), DIAMOND (Bergerhoff et al., 1996)
and
publCIF (Westrip, 2010)
;
_computing_structure_refinement  'SHELXTL-NT (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL-NT (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0563
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_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            33131
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.38
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  0.9478
_exptl_absorpt_correction_T_min  0.9132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.266
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3255
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0477
_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)+(0.0753P)²+1.2945P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1430
_reflns_number_gt                2488
_reflns_number_total             3255
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jh2215.cif
_cod_data_source_block           I
_cod_original_cell_volume        3694.0(14)
_cod_original_sg_symbol_Hall     '-P 2n 2ab '
_cod_database_code               2227720
_cod_database_fobs_code          2227720
loop_
_symmetry_equiv_pos_as_xyz
'X, Y, Z'
'1/2 - X, 1/2 - Y, 1/2 + Z'
'1/2 + X, 1/2 - Y, - Z'
'- X, Y, 1/2 - Z'
'- X, - Y, - Z'
'1/2 + X, 1/2 + Y, 1/2 - Z'
'1/2 - X, 1/2 + Y, Z'
'X, - Y, 1/2 + Z'
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
C C1 0.30111(9) 1.0099(3) -0.01807(17) 0.0476(7) Uani d . 1 . .
C C2 0.27124(10) 1.0650(4) 0.0426(2) 0.0579(8) Uani d . 1 . .
H H2 0.2818 1.1180 0.0915 0.069 Uiso calc R 1 . .
C C3 0.22466(11) 1.0411(4) 0.0306(3) 0.0694(9) Uani d . 1 . .
H H3 0.2044 1.0776 0.0719 0.083 Uiso calc R 1 . .
C C4 0.20921(10) 0.9652(4) -0.0408(2) 0.0679(9) Uani d . 1 . .
H H4 0.1782 0.9534 -0.0487 0.081 Uiso calc R 1 . .
C C5 0.23901(10) 0.9033(4) -0.1037(2) 0.0562(8) Uani d . 1 . .
C C6 0.22292(12) 0.8195(5) -0.1765(2) 0.0724(10) Uani d . 1 . .
H H6 0.1919 0.8057 -0.1838 0.087 Uiso calc R 1 . .
C C7 0.25155(14) 0.7585(5) -0.2363(2) 0.0794(11) Uani d . 1 . .
H H7 0.2402 0.7041 -0.2842 0.095 Uiso calc R 1 . .
C C8 0.29822(13) 0.7776(5) -0.2257(2) 0.0733(9) Uani d . 1 . .
H H8 0.3178 0.7355 -0.2669 0.088 Uiso calc R 1 . .
C C9 0.31544(11) 0.8571(4) -0.15595(18) 0.0573(7) Uani d . 1 . .
H H9 0.3466 0.8675 -0.1499 0.069 Uiso calc R 1 . .
C C10 0.28653(9) 0.9240(3) -0.09264(18) 0.0484(7) Uani d . 1 . .
C C11 0.38848(8) 0.8134(3) 0.08417(17) 0.0433(6) Uani d . 1 . .
C C12 0.40857(8) 0.5962(3) 0.17449(16) 0.0436(6) Uani d . 1 . .
C C13 0.39714(10) 0.7109(4) 0.23161(18) 0.0557(7) Uani d . 1 . .
H H13 0.3984 0.6930 0.2902 0.067 Uiso calc R 1 . .
C C14 0.42320(9) 0.4204(3) 0.18915(18) 0.0496(7) Uani d . 1 . .
H H14A 0.4013 0.3457 0.1630 0.060 Uiso calc R 1 . .
H H14B 0.4230 0.3986 0.2500 0.060 Uiso calc R 1 . .
C C15 0.46919(9) 0.3790(4) 0.15489(18) 0.0508(7) Uani d . 1 . .
C C16 0.51735(11) 0.1490(5) 0.1211(3) 0.0821(11) Uani d . 1 . .
H H16A 0.5425 0.1802 0.1575 0.099 Uiso calc R 1 . .
H H16B 0.5228 0.1929 0.0643 0.099 Uiso calc R 1 . .
C C17 0.51244(15) -0.0349(5) 0.1183(3) 0.1036(14) Uani d . 1 . .
H H17A 0.5089 -0.0774 0.1752 0.155 Uiso calc R 1 . .
H H17B 0.5389 -0.0835 0.0928 0.155 Uiso calc R 1 . .
H H17C 0.4863 -0.0637 0.0850 0.155 Uiso calc R 1 . .
N N1 0.38373(7) 0.8826(3) 0.00845(14) 0.0499(6) Uani d . 1 . .
N N2 0.40331(7) 0.6559(3) 0.09207(13) 0.0428(5) Uani d . 1 . .
H H2A 0.4093 0.5947 0.0483 0.051 Uiso calc R 1 . .
O O1 0.36124(7) 1.1601(2) 0.07509(14) 0.0648(6) Uani d . 1 . .
O O2 0.37576(7) 1.1370(3) -0.07715(14) 0.0639(6) Uani d . 1 . .
O O3 0.49668(8) 0.4789(3) 0.13212(19) 0.0858(8) Uani d . 1 . .
O O4 0.47548(7) 0.2156(3) 0.15495(15) 0.0698(6) Uani d . 1 . .
O O5 0.57738(8) 0.5513(3) 0.04480(16) 0.0876(8) Uani d . 1 . .
H H5A 0.5842 0.6535 0.0484 0.131 Uiso d R 1 . .
H H5B 0.5518 0.5450 0.0679 0.131 Uiso d R 1 . .
S S1 0.35869(2) 1.05939(9) -0.00081(5) 0.0514(2) Uani d . 1 . .
S S2 0.37963(3) 0.89724(10) 0.18608(5) 0.0577(3) Uani d . 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C10 . . 121.9(3) ?
C2 C1 S1 . . 116.3(2) ?
C10 C1 S1 . . 121.7(2) ?
C1 C2 C3 . . 119.8(3) ?
C1 C2 H2 . . 120.1 ?
C3 C2 H2 . . 120.1 ?
C4 C3 C2 . . 120.2(3) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C3 C4 C5 . . 121.5(3) ?
C3 C4 H4 . . 119.2 ?
C5 C4 H4 . . 119.2 ?
C6 C5 C4 . . 121.4(3) ?
C6 C5 C10 . . 119.2(3) ?
C4 C5 C10 . . 119.4(3) ?
C7 C6 C5 . . 121.4(3) ?
C7 C6 H6 . . 119.3 ?
C5 C6 H6 . . 119.3 ?
C6 C7 C8 . . 119.8(3) ?
C6 C7 H7 . . 120.1 ?
C8 C7 H7 . . 120.1 ?
C9 C8 C7 . . 120.9(3) ?
C9 C8 H8 . . 119.5 ?
C7 C8 H8 . . 119.5 ?
C8 C9 C10 . . 120.8(3) ?
C8 C9 H9 . . 119.6 ?
C10 C9 H9 . . 119.6 ?
C9 C10 C1 . . 125.1(3) ?
C9 C10 C5 . . 117.9(3) ?
C1 C10 C5 . . 117.0(3) ?
N1 C11 N2 . . 120.8(2) ?
N1 C11 S2 . . 130.3(2) ?
N2 C11 S2 . . 108.83(19) ?
C13 C12 N2 . . 111.4(2) ?
C13 C12 C14 . . 128.4(2) ?
N2 C12 C14 . . 120.1(2) ?
C12 C13 S2 . . 113.0(2) ?
C12 C13 H13 . . 123.5 ?
S2 C13 H13 . . 123.5 ?
C12 C14 C15 . . 114.6(2) ?
C12 C14 H14A . . 108.6 ?
C15 C14 H14A . . 108.6 ?
C12 C14 H14B . . 108.6 ?
C15 C14 H14B . . 108.6 ?
H14A C14 H14B . . 107.6 ?
O3 C15 O4 . . 124.4(3) ?
O3 C15 C14 . . 125.4(3) ?
O4 C15 C14 . . 110.2(2) ?
O4 C16 C17 . . 106.9(3) ?
O4 C16 H16A . . 110.3 ?
C17 C16 H16A . . 110.3 ?
O4 C16 H16B . . 110.3 ?
C17 C16 H16B . . 110.3 ?
H16A C16 H16B . . 108.6 ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C11 N1 S1 . . 120.0(2) ?
C11 N2 C12 . . 116.5(2) ?
C11 N2 H2A . . 121.8 ?
C12 N2 H2A . . 121.8 ?
C15 O4 C16 . . 118.9(3) ?
H5A O5 H5B . . 104.1 ?
O1 S1 O2 . . 115.50(13) ?
O1 S1 N1 . . 113.12(12) ?
O2 S1 N1 . . 106.95(13) ?
O1 S1 C1 . . 107.55(13) ?
O2 S1 C1 . . 107.85(13) ?
N1 S1 C1 . . 105.29(12) ?
C13 S2 C11 . . 90.25(13) ?
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
C1 C2 . 1.370(4) ?
C1 C10 . 1.421(4) ?
C1 S1 . 1.769(3) ?
C2 C3 . 1.404(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.352(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.411(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.406(4) ?
C5 C10 . 1.426(4) ?
C6 C7 . 1.353(5) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.399(5) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.363(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.414(4) ?
C9 H9 . 0.9300 ?
C11 N1 . 1.316(3) ?
C11 N2 . 1.335(3) ?
C11 S2 . 1.751(3) ?
C12 C13 . 1.323(4) ?
C12 N2 . 1.385(3) ?
C12 C14 . 1.484(4) ?
C13 S2 . 1.727(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.499(4) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 O3 . 1.193(3) ?
C15 O4 . 1.315(3) ?
C16 O4 . 1.448(4) ?
C16 C17 . 1.473(5) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
N1 S1 . 1.598(2) ?
N2 H2A . 0.8600 ?
O1 S1 . 1.437(2) ?
O2 S1 . 1.439(2) ?
O5 H5A . 0.8399 ?
O5 H5B . 0.8400 ?
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
N2 H2A O5 5_665 0.86 1.91 2.767(3) 177
O5 H5A O2 5_675 0.84 2.10 2.889(3) 157
C13 H13 O2 8_575 0.93 2.57 3.295(4) 135
C14 H14A O1 1_545 0.97 2.34 3.295(3) 167
C17 H17B O2 5_665 0.96 2.57 3.466(5) 155
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 C1 C2 C3 . . . . -1.8(4) ?
S1 C1 C2 C3 . . . . 175.5(2) ?
C1 C2 C3 C4 . . . . -0.5(5) ?
C2 C3 C4 C5 . . . . 2.1(5) ?
C3 C4 C5 C6 . . . . 177.9(3) ?
C3 C4 C5 C10 . . . . -1.3(4) ?
C4 C5 C6 C7 . . . . -179.3(3) ?
C10 C5 C6 C7 . . . . -0.1(5) ?
C5 C6 C7 C8 . . . . 0.4(5) ?
C6 C7 C8 C9 . . . . 0.0(5) ?
C7 C8 C9 C10 . . . . -0.7(5) ?
C8 C9 C10 C1 . . . . -179.5(3) ?
C8 C9 C10 C5 . . . . 0.9(4) ?
C2 C1 C10 C9 . . . . -177.0(3) ?
S1 C1 C10 C9 . . . . 5.7(4) ?
C2 C1 C10 C5 . . . . 2.5(4) ?
S1 C1 C10 C5 . . . . -174.7(2) ?
C6 C5 C10 C9 . . . . -0.5(4) ?
C4 C5 C10 C9 . . . . 178.6(3) ?
C6 C5 C10 C1 . . . . 179.9(3) ?
C4 C5 C10 C1 . . . . -1.0(4) ?
N2 C12 C13 S2 . . . . -0.2(3) ?
C14 C12 C13 S2 . . . . -177.1(2) ?
C13 C12 C14 C15 . . . . -121.0(3) ?
N2 C12 C14 C15 . . . . 62.3(3) ?
C12 C14 C15 O3 . . . . 14.1(4) ?
C12 C14 C15 O4 . . . . -167.2(2) ?
N2 C11 N1 S1 . . . . 170.26(19) ?
S2 C11 N1 S1 . . . . -11.7(3) ?
N1 C11 N2 C12 . . . . 178.0(2) ?
S2 C11 N2 C12 . . . . -0.4(3) ?
C13 C12 N2 C11 . . . . 0.4(3) ?
C14 C12 N2 C11 . . . . 177.6(2) ?
O3 C15 O4 C16 . . . . -3.5(5) ?
C14 C15 O4 C16 . . . . 177.7(3) ?
C17 C16 O4 C15 . . . . -172.3(3) ?
C11 N1 S1 O1 . . . . 26.1(3) ?
C11 N1 S1 O2 . . . . 154.4(2) ?
C11 N1 S1 C1 . . . . -91.0(2) ?
C2 C1 S1 O1 . . . . -3.2(2) ?
C10 C1 S1 O1 . . . . 174.1(2) ?
C2 C1 S1 O2 . . . . -128.4(2) ?
C10 C1 S1 O2 . . . . 48.9(2) ?
C2 C1 S1 N1 . . . . 117.7(2) ?
C10 C1 S1 N1 . . . . -65.0(2) ?
C12 C13 S2 C11 . . . . 0.0(2) ?
N1 C11 S2 C13 . . . . -177.9(3) ?
N2 C11 S2 C13 . . . . 0.27(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656272
