#------------------------------------------------------------------------------
#$Date: 2015-12-10 09:33:55 +0200 (Thu, 10 Dec 2015) $
#$Revision: 171402 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/34/7223432.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_7223432
loop_
_publ_author_name
'Balakrishnan, C.'
'M, Theetharappan'
'Natarajan, Satheesh'
'S, Thalamuthu'
'M A, Neelakantan'
_publ_section_title
;
 Fluorescence response of a thiazolidine carboxylic acid derivative for
 the selective and nanomolar detection of Zn(II) ions: quantum chemical
 calculations and application in real samples
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA21277D
_journal_year                    2015
_chemical_compound_source        -
_chemical_formula_moiety         '(C13 H16 N1 O4) + 0.333(C1 H4 O)'
_chemical_formula_sum            'C13.33 H17.33 N O4.33 S'
_chemical_formula_weight         293.01
_chemical_melting_point          433
_chemical_name_systematic        o-vanillylidene-D-Penicillamine
_space_group_IT_number           143
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 3'
_symmetry_space_group_name_H-M   'P 3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-12-12 deposited with the CCDC.
2015-12-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            3
_cell_length_a                   14.014(2)
_cell_length_b                   14.014(2)
_cell_length_c                   6.4750(10)
_cell_measurement_reflns_used    1621
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.1
_cell_measurement_theta_min      2.8
_cell_volume                     1101.3(3)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ 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  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4700
_diffrn_reflns_theta_full        22.83
_diffrn_reflns_theta_max         22.83
_diffrn_reflns_theta_min         2.91
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             465
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(15)
_refine_ls_extinction_coef       0.036(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         1798
_refine_ls_number_restraints     146
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0458
_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)+(0.0588P)²+0.3598P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1132
_reflns_number_gt                1562
_reflns_number_total             1798
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra21277d2.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      P3
_cod_database_code               7223432
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1556(4) 0.4192(4) -0.0255(7) 0.0609(13) Uani 1 1 d . A .
H1 H 0.1150 0.4148 -0.1423 0.073 Uiso 1 1 calc R . .
C2 C 0.2661(5) 0.4880(4) -0.0231(7) 0.0719(15) Uani 1 1 d . . .
H2 H 0.3004 0.5295 -0.1403 0.086 Uiso 1 1 calc R . .
C3 C 0.3300(4) 0.4985(4) 0.1499(8) 0.0659(13) Uani 1 1 d . . .
H3 H 0.4057 0.5465 0.1494 0.079 Uiso 1 1 calc R . .
C4 C 0.2783(4) 0.4361(5) 0.3210(8) 0.0642(13) Uani 1 1 d . . .
C5 C 0.1643(4) 0.3637(5) 0.3196(7) 0.0609(13) Uani 1 1 d . A .
C6 C 0.1038(4) 0.3563(4) 0.1441(7) 0.0586(12) Uani 1 1 d . . .
C9 C -0.1846(4) 0.2011(4) -0.1194(8) 0.0583(12) Uani 1 1 d D . .
C10 C -0.2827(5) 0.1149(6) -0.0065(11) 0.100(2) Uani 1 1 d . A .
H10A H -0.2591 0.0944 0.1167 0.151 Uiso 1 1 calc R . .
H10B H -0.3220 0.0514 -0.0933 0.151 Uiso 1 1 calc R . .
H10C H -0.3301 0.1434 0.0299 0.151 Uiso 1 1 calc R . .
C11 C -0.2249(8) 0.2318(7) -0.3118(12) 0.129(3) Uani 1 1 d . A .
H11A H -0.1630 0.2873 -0.3872 0.194 Uiso 1 1 calc R . .
H11B H -0.2724 0.2598 -0.2729 0.194 Uiso 1 1 calc R . .
H11C H -0.2648 0.1678 -0.3972 0.194 Uiso 1 1 calc R . .
C12 C 0.4459(5) 0.5054(6) 0.5054(10) 0.102(2) Uani 1 1 d . . .
H12A H 0.4720 0.5004 0.6398 0.153 Uiso 1 1 calc R . .
H12B H 0.4667 0.5806 0.4773 0.153 Uiso 1 1 calc R . .
H12C H 0.4779 0.4801 0.4032 0.153 Uiso 1 1 calc R . .
C7 C -0.0246(12) 0.2594(12) 0.118(2) 0.043(3) Uani 0.494(7) 1 d PDU A 1
H7 H -0.0528 0.2271 0.2539 0.051 Uiso 0.494(7) 1 calc PR A 1
C8 C -0.1082(9) 0.1652(9) -0.2118(16) 0.045(2) Uani 0.494(7) 1 d PDU A 1
H8 H -0.0572 0.2258 -0.3013 0.053 Uiso 0.494(7) 1 calc PR A 1
N1 N -0.0429(7) 0.1683(7) -0.0273(15) 0.0345(19) Uani 0.494(7) 1 d PDU A 1
O4 O -0.1714(9) 0.0713(10) -0.5328(17) 0.119(4) Uani 0.494(7) 1 d PU A 1
O3 O -0.1758(9) -0.0197(9) -0.262(2) 0.100(3) Uani 0.494(7) 1 d PDU A 1
C13 C -0.1546(12) 0.0599(11) -0.344(3) 0.071(4) Uani 0.494(7) 1 d PDU A 1
C7' C -0.0125(13) 0.2941(10) 0.172(2) 0.053(3) Uani 0.506(7) 1 d PDU A 2
H7' H -0.0298 0.2903 0.3192 0.064 Uiso 0.506(7) 1 calc PR A 2
C8' C -0.0925(13) 0.1649(10) -0.116(2) 0.061(3) Uani 0.506(7) 1 d PDU A 2
H8' H -0.0338 0.2102 -0.2141 0.074 Uiso 0.506(7) 1 calc PR A 2
N1' N -0.0463(8) 0.1839(9) 0.0956(19) 0.060(2) Uani 0.506(7) 1 d PDU A 2
O4' O -0.1916(10) 0.0198(9) -0.381(2) 0.089(3) Uani 0.506(7) 1 d PU A 2
O3' O -0.1577(6) -0.0217(5) -0.0604(16) 0.079(3) Uani 0.506(7) 1 d PDU A 2
C13' C -0.1497(8) 0.0436(9) -0.185(2) 0.064(3) Uani 0.506(7) 1 d PDU A 2
C14 C -0.0209(9) 0.0623(9) 0.3577(17) 0.038(3) Uani 0.33 1 d P . 3
O5 O -0.1128(8) -0.0155(7) 0.2307(14) 0.064(3) Uani 0.33 1 d P B 3
O1 O 0.1123(3) 0.3033(4) 0.4892(5) 0.0848(13) Uani 1 1 d . . .
O2 O 0.3298(3) 0.4391(4) 0.4991(5) 0.0827(12) Uani 1 1 d . . .
S1 S -0.10155(12) 0.32568(12) 0.0295(3) 0.0794(5) Uani 1 1 d D A .
H1A H 0.016(5) 0.166(9) -0.035(16) 0.07(2) Uiso 0.494(7) 1 d PD A 1
H1' H -0.087(6) 0.133(3) 0.178(4) 0.07(2) Uiso 0.506(7) 1 d PD A 2
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C6 120.0(4) . .
C2 C1 H1 120.0 . .
C6 C1 H1 120.0 . .
C1 C2 C3 121.9(5) . .
C1 C2 H2 119.0 . .
C3 C2 H2 119.0 . .
C4 C3 C2 118.3(5) . .
C4 C3 H3 120.8 . .
C2 C3 H3 120.8 . .
O2 C4 C3 124.5(5) . .
O2 C4 C5 115.2(4) . .
C3 C4 C5 120.3(5) . .
O1 C5 C6 119.9(5) . .
O1 C5 C4 120.6(4) . .
C6 C5 C4 119.4(4) . .
C1 C6 C5 120.1(4) . .
C1 C6 C7' 124.9(7) . .
C5 C6 C7' 114.3(7) . .
C1 C6 C7 117.4(6) . .
C5 C6 C7 121.7(6) . .
C10 C9 C8 116.3(6) . .
C10 C9 C11 108.0(5) . .
C8 C9 C11 101.2(6) . .
C10 C9 C8' 107.4(6) . .
C8 C9 C8' 24.2(5) . .
C11 C9 C8' 125.0(7) . .
C10 C9 S1 114.0(4) . .
C8 C9 S1 108.0(5) . .
C11 C9 S1 108.3(4) . .
C8' C9 S1 93.8(5) . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C9 C11 H11A 109.5 . .
C9 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C9 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
O2 C12 H12A 109.5 . .
O2 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
O2 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
N1 C7 C6 114.9(9) . .
N1 C7 S1 110.1(8) . .
C6 C7 S1 107.1(8) . .
N1 C7 H7 108.2 . .
C6 C7 H7 108.2 . .
S1 C7 H7 108.2 . .
N1 C8 C9 101.5(7) . .
N1 C8 C13 115.5(11) . .
C9 C8 C13 120.5(10) . .
N1 C8 H8 106.1 . .
C9 C8 H8 106.1 . .
C13 C8 H8 106.1 . .
C8 N1 C7 111.5(8) . .
C8 N1 H1A 123(7) . .
C7 N1 H1A 108(7) . .
O3 C13 O4 127.0(15) . .
O3 C13 C8 117.3(16) . .
O4 C13 C8 115.5(13) . .
C6 C7' N1' 105.8(12) . .
C6 C7' S1 120.9(9) . .
N1' C7' S1 101.0(8) . .
C6 C7' H7' 109.4 . .
N1' C7' H7' 109.4 . .
S1 C7' H7' 109.4 . .
N1' C8' C13' 113.9(12) . .
N1' C8' C9 107.7(9) . .
C13' C8' C9 106.7(10) . .
N1' C8' H8' 109.5 . .
C13' C8' H8' 109.5 . .
C9 C8' H8' 109.5 . .
C7' N1' C8' 112.7(10) . .
C7' N1' H1' 114(3) . .
C8' N1' H1' 112(3) . .
O3' C13' O4' 125.6(12) . .
O3' C13' C8' 117.0(12) . .
O4' C13' C8' 117.4(12) . .
O5 C14 O5 111.2(9) . 3
O5 C14 C14 108.2(6) . 3
O5 C14 C14 49.3(7) 3 3
O5 C14 C14 59.6(7) . 2
O5 C14 C14 99.8(6) 3 2
C14 C14 C14 60.000(1) 3 2
C14 O5 C14 71.1(9) . 2
C4 O2 C12 117.8(4) . .
C7' S1 C9 103.2(4) . .
C9 S1 C7 86.2(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.355(7) .
C1 C6 1.367(6) .
C1 H1 0.9300 .
C2 C3 1.396(8) .
C2 H2 0.9300 .
C3 C4 1.372(7) .
C3 H3 0.9300 .
C4 O2 1.350(6) .
C4 C5 1.400(7) .
C5 O1 1.355(5) .
C5 C6 1.390(7) .
C6 C7' 1.424(16) .
C6 C7 1.634(15) .
C9 C10 1.491(8) .
C9 C8 1.514(13) .
C9 C11 1.517(8) .
C9 C8' 1.605(19) .
C9 S1 1.817(5) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 O2 1.415(6) .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C7 N1 1.500(13) .
C7 S1 1.831(13) .
C7 H7 0.9800 .
C8 N1 1.493(12) .
C8 C13 1.541(15) .
C8 H8 0.9800 .
N1 H1A 0.85(2) .
O4 C13 1.27(2) .
O3 C13 1.134(17) .
C7' N1' 1.456(13) .
C7' S1 1.776(15) .
C7' H7' 0.9800 .
C8' N1' 1.481(13) .
C8' C13' 1.540(14) .
C8' H8' 0.9800 .
N1' H1' 0.85(2) .
O4' C13' 1.372(19) .
O3' C13' 1.181(12) .
C14 O5 1.456(14) .
C14 O5 1.657(14) 3
C14 C14 1.818(19) 3
C14 C14 1.818(19) 2
O5 C14 1.657(14) 2
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 -1.0(8) . .
C1 C2 C3 C4 0.5(8) . .
C2 C3 C4 O2 -179.1(5) . .
C2 C3 C4 C5 0.2(7) . .
O2 C4 C5 O1 0.7(7) . .
C3 C4 C5 O1 -178.8(5) . .
O2 C4 C5 C6 178.9(5) . .
C3 C4 C5 C6 -0.5(7) . .
C2 C1 C6 C5 0.7(7) . .
C2 C1 C6 C7' 170.0(8) . .
C2 C1 C6 C7 -169.1(6) . .
O1 C5 C6 C1 178.3(5) . .
C4 C5 C6 C1 0.0(7) . .
O1 C5 C6 C7' 7.9(9) . .
C4 C5 C6 C7' -170.4(7) . .
O1 C5 C6 C7 -12.3(8) . .
C4 C5 C6 C7 169.4(6) . .
C1 C6 C7 N1 65.2(11) . .
C5 C6 C7 N1 -104.4(9) . .
C7' C6 C7 N1 -177(4) . .
C1 C6 C7 S1 -57.4(8) . .
C5 C6 C7 S1 132.9(6) . .
C7' C6 C7 S1 60(3) . .
C10 C9 C8 N1 -79.9(8) . .
C11 C9 C8 N1 163.3(7) . .
C8' C9 C8 N1 -6.6(14) . .
S1 C9 C8 N1 49.7(8) . .
C10 C9 C8 C13 49.1(13) . .
C11 C9 C8 C13 -67.6(12) . .
C8' C9 C8 C13 122(2) . .
S1 C9 C8 C13 178.8(10) . .
C9 C8 N1 C7 -34.2(11) . .
C13 C8 N1 C7 -166.4(11) . .
C6 C7 N1 C8 -115.1(10) . .
S1 C7 N1 C8 5.9(12) . .
N1 C8 C13 O3 30.5(19) . .
C9 C8 C13 O3 -92.0(17) . .
N1 C8 C13 O4 -153.9(12) . .
C9 C8 C13 O4 83.6(16) . .
C1 C6 C7' N1' 93.1(10) . .
C5 C6 C7' N1' -97.0(9) . .
C7 C6 C7' N1' 20(2) . .
C1 C6 C7' S1 -20.6(14) . .
C5 C6 C7' S1 149.2(7) . .
C7 C6 C7' S1 -94(3) . .
C10 C9 C8' N1' -73.7(9) . .
C8 C9 C8' N1' 170(2) . .
C11 C9 C8' N1' 158.4(7) . .
S1 C9 C8' N1' 42.9(8) . .
C10 C9 C8' C13' 49.0(11) . .
C8 C9 C8' C13' -66.9(17) . .
C11 C9 C8' C13' -78.9(11) . .
S1 C9 C8' C13' 165.6(8) . .
C6 C7' N1' C8' -99.8(12) . .
S1 C7' N1' C8' 27.0(14) . .
C13' C8' N1' C7' -168.6(12) . .
C9 C8' N1' C7' -50.4(13) . .
N1' C8' C13' O3' 5.0(16) . .
C9 C8' C13' O3' -113.7(11) . .
N1' C8' C13' O4' -178.0(11) . .
C9 C8' C13' O4' 63.3(12) . .
O5 C14 O5 C14 89.1(7) 3 2
C14 C14 O5 C14 36.6(5) 3 2
C3 C4 O2 C12 -4.5(8) . .
C5 C4 O2 C12 176.1(5) . .
C6 C7' S1 C9 117.9(9) . .
N1' C7' S1 C9 1.8(10) . .
C6 C7' S1 C7 102(4) . .
N1' C7' S1 C7 -14(2) . .
C10 C9 S1 C7' 85.5(7) . .
C8 C9 S1 C7' -45.5(8) . .
C11 C9 S1 C7' -154.3(7) . .
C8' C9 S1 C7' -25.5(8) . .
C10 C9 S1 C7 90.1(6) . .
C8 C9 S1 C7 -40.9(7) . .
C11 C9 S1 C7 -149.7(7) . .
C8' C9 S1 C7 -20.9(7) . .
N1 C7 S1 C7' -175(4) . .
C6 C7 S1 C7' -50(3) . .
N1 C7 S1 C9 19.7(8) . .
C6 C7 S1 C9 145.3(6) . .
