#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/13/2201367.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_2201367
loop_
_publ_author_name
'A. Abdul Ajees'
'S. Karthikeyan'
'C. V. Yelamaggad'
'B. V. Badami'
_publ_section_title
;
 4-(2-Benzoylhydrazinothiazol-4-yl)-3-phenylsydnone
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o784
_journal_page_last               o786
_journal_paper_doi               10.1107/S1600536802010668
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C18 H13 N5 O3 S'
_chemical_formula_moiety         'C18 H13 N5 O3 S'
_chemical_formula_sum            'C18 H13 N5 O3 S'
_chemical_formula_weight         379.39
_chemical_name_common
;
4-2(2'-Benzoylhydrazino-4'-thiazolyl)-3-phenylsydnone
;
_chemical_name_systematic
;
4-2(2'-Benzoylhydrazino-4'-thiazolyl)-3-phenylsydnone
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                81.54(2)
_cell_angle_beta                 81.74(2)
_cell_angle_gamma                71.59(2)
_cell_formula_units_Z            2
_cell_length_a                   8.290(2)
_cell_length_b                   9.646(3)
_cell_length_c                   11.715(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      14
_cell_volume                     874.4(4)
_computing_cell_refinement       'SDP (Frenz, 1978)'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'CAD-4 Software'
_computing_molecular_graphics    'ZORTEP (Zsolnai, 1997)'
_computing_publication_material  'PARST97 (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.938
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type  'Enraf-Nonius CAD-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     1.5418
_diffrn_reflns_av_R_equivalents  0.012
_diffrn_reflns_av_sigmaI/netI    0.1119
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3306
_diffrn_reflns_theta_full        69.92
_diffrn_reflns_theta_max         69.92
_diffrn_reflns_theta_min         3.84
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_time  120min
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.915
_exptl_absorpt_correction_T_max  0.682
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.34
_refine_ls_extinction_coef       0.0056(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.048
_refine_ls_R_factor_gt           0.043
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0778P)²+0.1813P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.122
_refine_ls_wR_factor_ref         0.129
_reflns_number_gt                2709
_reflns_number_total             3105
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6128.cif
_cod_data_source_block           I
_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 
;
_cod_database_code               2201367
_cod_database_fobs_code          2201367
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_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' 0.77553(6) 0.40163(6) 0.25273(5) 0.0627(2) Uani d . 1 . . S
C2' 0.5537(2) 0.4777(2) 0.26516(18) 0.0506(4) Uani d . 1 . . C
N3' 0.49125(19) 0.56841(19) 0.17799(15) 0.0528(4) Uani d . 1 . . N
C4' 0.6231(2) 0.5833(2) 0.09467(18) 0.0529(5) Uani d . 1 . . C
C5' 0.7828(3) 0.5035(3) 0.1203(2) 0.0630(6) Uani d . 1 . . C
H5' 0.8826 0.5040 0.0727 0.076 Uiso calc R 1 . . H
O1 0.5838(2) 0.7779(2) -0.19526(14) 0.0747(5) Uani d . 1 . . O
N2 0.4277(3) 0.8478(2) -0.13855(16) 0.0722(5) Uani d . 1 . . N
N3 0.4372(2) 0.7827(2) -0.03141(15) 0.0572(4) Uani d . 1 . . N
C4 0.5842(3) 0.6765(2) -0.01223(18) 0.0558(5) Uani d . 1 . . C
C5 0.6856(3) 0.6701(3) -0.1213(2) 0.0642(6) Uani d . 1 . . C
O5 0.8269(2) 0.5972(2) -0.15687(16) 0.0799(5) Uani d . 1 . . O
N6 0.4578(2) 0.4348(2) 0.36025(16) 0.0603(5) Uani d . 1 . . N
H6 0.5035 0.3653 0.4115 0.072 Uiso calc R 1 . . H
N7 0.2838(2) 0.5076(2) 0.37084(15) 0.0566(4) Uani d . 1 . . N
H7 0.2153 0.4734 0.3431 0.068 Uiso calc R 1 . . H
C8 0.2208(2) 0.6310(2) 0.42400(16) 0.0518(4) Uani d . 1 . . C
O8 0.3130(2) 0.68021(19) 0.46809(15) 0.0731(5) Uani d . 1 . . O
C9 0.0320(2) 0.7012(2) 0.42925(17) 0.0528(5) Uani d . 1 . . C
C10 -0.0378(3) 0.8164(3) 0.4954(3) 0.0889(9) Uani d . 1 . . C
H10 0.0317 0.8467 0.5357 0.107 Uiso calc R 1 . . H
C11 -0.2118(4) 0.8871(4) 0.5020(3) 0.1177(14) Uani d . 1 . . C
H11 -0.2589 0.9634 0.5484 0.141 Uiso calc R 1 . . H
C12 -0.3153(3) 0.8463(4) 0.4413(3) 0.0946(9) Uani d . 1 . . C
H12 -0.4318 0.8957 0.4454 0.114 Uiso calc R 1 . . H
C13 -0.2470(3) 0.7328(3) 0.3748(3) 0.0772(7) Uani d . 1 . . C
H13 -0.3164 0.7050 0.3327 0.093 Uiso calc R 1 . . H
C14 -0.0735(3) 0.6592(3) 0.3702(2) 0.0640(6) Uani d . 1 . . C
H14 -0.0277 0.5801 0.3264 0.077 Uiso calc R 1 . . H
C15 0.2898(3) 0.8422(2) 0.05030(18) 0.0576(5) Uani d . 1 . . C
C16 0.3010(4) 0.9384(3) 0.1211(2) 0.0812(7) Uani d . 1 . . C
H16 0.4020 0.9613 0.1205 0.097 Uiso calc R 1 . . H
C17 0.1566(4) 1.0009(3) 0.1939(3) 0.0927(9) Uani d . 1 . . C
H17 0.1605 1.0665 0.2435 0.111 Uiso calc R 1 . . H
C18 0.0090(3) 0.9668(3) 0.1934(2) 0.0794(8) Uani d . 1 . . C
H18 -0.0877 1.0107 0.2415 0.095 Uiso calc R 1 . . H
C19 0.0029(3) 0.8693(3) 0.1232(2) 0.0775(7) Uani d . 1 . . C
H19 -0.0976 0.8452 0.1247 0.093 Uiso calc R 1 . . H
C20 0.1438(3) 0.8053(3) 0.0494(2) 0.0679(6) Uani d . 1 . . C
H20 0.1396 0.7391 0.0005 0.082 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C5' S1' C2' 88.23(10)
N3' C2' N6 124.48(17)
N3' C2' S1' 115.83(15)
N6 C2' S1' 119.61(16)
C2' N3' C4' 109.53(16)
C5' C4' N3' 115.7(2)
C5' C4' C4 124.61(19)
N3' C4' C4 119.62(18)
C4' C5' S1' 110.64(16)
C4' C5' H5' 124.7
S1' C5' H5' 124.7
N2 O1 C5 111.69(16)
N3 N2 O1 103.30(17)
N2 N3 C4 115.62(17)
N2 N3 C15 114.90(17)
C4 N3 C15 129.40(18)
N3 C4 C5 105.1(2)
N3 C4 C4' 126.59(18)
C5 C4 C4' 128.2(2)
O5 C5 O1 120.5(2)
O5 C5 C4 135.2(2)
O1 C5 C4 104.28(19)
C2' N6 N7 117.30(17)
C2' N6 H6 121.3
N7 N6 H6 121.3
C8 N7 N6 120.84(17)
C8 N7 H7 119.6
N6 N7 H7 119.6
O8 C8 N7 121.57(19)
O8 C8 C9 122.09(19)
N7 C8 C9 116.31(18)
C10 C9 C14 118.9(2)
C10 C9 C8 117.3(2)
C14 C9 C8 123.78(18)
C9 C10 C11 119.8(3)
C9 C10 H10 120.1
C11 C10 H10 120.1
C12 C11 C10 120.9(3)
C12 C11 H11 119.6
C10 C11 H11 119.6
C13 C12 C11 119.7(2)
C13 C12 H12 120.2
C11 C12 H12 120.2
C12 C13 C14 119.7(2)
C12 C13 H13 120.2
C14 C13 H13 120.2
C9 C14 C13 121.0(2)
C9 C14 H14 119.5
C13 C14 H14 119.5
C16 C15 C20 122.7(2)
C16 C15 N3 118.2(2)
C20 C15 N3 119.1(2)
C15 C16 C17 117.7(3)
C15 C16 H16 121.1
C17 C16 H16 121.1
C18 C17 C16 120.5(3)
C18 C17 H17 119.7
C16 C17 H17 119.7
C19 C18 C17 120.2(2)
C19 C18 H18 119.9
C17 C18 H18 119.9
C18 C19 C20 120.8(3)
C18 C19 H19 119.6
C20 C19 H19 119.6
C15 C20 C19 118.0(2)
C15 C20 H20 121.0
C19 C20 H20 121.0
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' C5' . 1.714(3) ?
S1' C2' . 1.7446(19) ?
C2' N3' . 1.296(3) ?
C2' N6 . 1.365(3) ?
N3' C4' . 1.385(2) ?
C4' C5' . 1.356(3) ?
C4' C4 . 1.443(3) ?
C5' H5' . 0.93 ?
O1 N2 . 1.380(2) ?
O1 C5 . 1.391(3) ?
N2 N3 . 1.319(3) ?
N3 C4 . 1.344(3) ?
N3 C15 . 1.457(3) ?
C4 C5 . 1.423(3) ?
C5 O5 . 1.210(3) ?
N6 N7 . 1.387(2) ?
N6 H6 . 0.86 ?
N7 C8 . 1.345(3) ?
N7 H7 . 0.86 ?
C8 O8 . 1.221(2) ?
C8 C9 . 1.492(3) ?
C9 C10 . 1.374(3) ?
C9 C14 . 1.375(3) ?
C10 C11 . 1.383(4) ?
C10 H10 . 0.93 ?
C11 C12 . 1.367(4) ?
C11 H11 . 0.93 ?
C12 C13 . 1.364(4) ?
C12 H12 . 0.93 ?
C13 C14 . 1.385(3) ?
C13 H13 . 0.93 ?
C14 H14 . 0.93 ?
C15 C16 . 1.363(3) ?
C15 C20 . 1.367(3) ?
C16 C17 . 1.388(4) ?
C16 H16 . 0.93 ?
C17 C18 . 1.365(4) ?
C17 H17 . 0.93 ?
C18 C19 . 1.354(4) ?
C18 H18 . 0.93 ?
C19 C20 . 1.380(3) ?
C19 H19 . 0.93 ?
C20 H20 . 0.93 ?
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
N6 H6 O8 2_666 0.86 2.12 2.827(2) 139
N7 H7 O5 2_665 0.86 2.48 3.185(3) 140
C5' H5' O5 2_765 0.93 2.58 3.144(3) 120
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
C5' S1' C2' N3' 1.04(16)
C5' S1' C2' N6 177.97(18)
N6 C2' N3' C4' -177.57(18)
S1' C2' N3' C4' -0.8(2)
C2' N3' C4' C5' 0.0(2)
C2' N3' C4' C4 178.47(17)
N3' C4' C5' S1' 0.7(2)
C4 C4' C5' S1' -177.61(16)
C2' S1' C5' C4' -0.93(17)
C5 O1 N2 N3 0.4(2)
O1 N2 N3 C4 -0.2(2)
O1 N2 N3 C15 176.71(18)
N2 N3 C4 C5 -0.1(2)
C15 N3 C4 C5 -176.5(2)
N2 N3 C4 C4' -176.17(19)
C15 N3 C4 C4' 7.5(3)
C5' C4' C4 N3 -163.0(2)
N3' C4' C4 N3 18.7(3)
C5' C4' C4 C5 21.8(3)
N3' C4' C4 C5 -156.5(2)
N2 O1 C5 O5 179.7(2)
N2 O1 C5 C4 -0.5(2)
N3 C4 C5 O5 -179.9(3)
C4' C4 C5 O5 -3.9(4)
N3 C4 C5 O1 0.3(2)
C4' C4 C5 O1 176.33(19)
N3' C2' N6 N7 -8.8(3)
S1' C2' N6 N7 174.58(14)
C2' N6 N7 C8 -88.2(2)
N6 N7 C8 O8 -2.6(3)
N6 N7 C8 C9 179.31(17)
O8 C8 C9 C10 -6.0(3)
N7 C8 C9 C10 172.1(2)
O8 C8 C9 C14 172.6(2)
N7 C8 C9 C14 -9.3(3)
C14 C9 C10 C11 0.4(5)
C8 C9 C10 C11 179.0(3)
C9 C10 C11 C12 -1.6(6)
C10 C11 C12 C13 1.1(6)
C11 C12 C13 C14 0.6(5)
C10 C9 C14 C13 1.3(4)
C8 C9 C14 C13 -177.3(2)
C12 C13 C14 C9 -1.8(4)
N2 N3 C15 C16 -99.3(3)
C4 N3 C15 C16 77.1(3)
N2 N3 C15 C20 77.6(3)
C4 N3 C15 C20 -106.0(3)
C20 C15 C16 C17 -0.4(4)
N3 C15 C16 C17 176.4(2)
C15 C16 C17 C18 -0.3(5)
C16 C17 C18 C19 1.2(5)
C17 C18 C19 C20 -1.4(4)
C16 C15 C20 C19 0.3(4)
N3 C15 C20 C19 -176.5(2)
C18 C19 C20 C15 0.7(4)
