#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/38/1503882.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_1503882
loop_
_publ_author_name
'Attanasi, Orazio A.'
'Crescentini, Lucia De'
'Favi, Gianfranco'
'Filippone, Paolino'
'Giorgi, Gianluca'
'Mantellini, Fabio'
'Moscatelli, Giada'
'Behalo, Mohamed S.'
_publ_section_title
;
 An efficient one-pot, three-component synthesis of 5-hydrazinoalkylidene
 rhodanines from 1,2-diaza-1,3-dienes.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2265
_journal_page_last               2268
_journal_paper_doi               10.1021/ol900545v
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C16 H19 N3 O3 S2'
_chemical_formula_sum            'C16 H19 N3 O3 S2'
_chemical_formula_weight         365.46
_chemical_name_systematic
;
(E)-benzyl 2-(1-(4-oxo-3-propyl-2-thioxothiazolidin-5-ylidene)-
ethyl)hydrazinecarboxylate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                   12.215(2)
_cell_length_b                   8.434(2)
_cell_length_c                   34.429(6)
_cell_measurement_reflns_used    48
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      34.779
_cell_measurement_theta_min      9.510
_cell_volume                     3546.9(12)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '2θ/ω 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  0.0691
_diffrn_reflns_av_sigmaI/netI    0.0682
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            6147
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.04
_diffrn_standards_decay_%        4.37
_diffrn_standards_interval_count 300
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3116
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0516
_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)+(0.0508P)²+1.3761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1313
_reflns_number_gt                1850
_reflns_number_total             3116
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol900545v_si_002.cif
_cod_data_source_block           urb
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               1503882
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
S1 S 0.13615(7) 0.20202(12) 0.55179(3) 0.0523(3) Uani 1 1 d .
C2 C 0.2158(3) 0.2302(4) 0.59254(10) 0.0484(9) Uani 1 1 d .
S2 S 0.16610(9) 0.29223(14) 0.63422(3) 0.0668(3) Uani 1 1 d .
N3 N 0.3231(2) 0.1929(3) 0.58478(8) 0.0463(7) Uani 1 1 d .
C4 C 0.3463(3) 0.1437(4) 0.54701(10) 0.0443(8) Uani 1 1 d .
O1 O 0.44008(19) 0.1106(3) 0.53621(7) 0.0579(7) Uani 1 1 d .
C5 C 0.2488(3) 0.1389(4) 0.52409(9) 0.0427(8) Uani 1 1 d .
C6 C 0.2417(3) 0.0903(4) 0.48642(9) 0.0429(8) Uani 1 1 d .
C7 C 0.1342(3) 0.0878(5) 0.46574(11) 0.0572(10) Uani 1 1 d .
H7A H 0.1398 0.1478 0.4421 0.086 Uiso 1 1 calc R
H7B H 0.0789 0.1337 0.4821 0.086 Uiso 1 1 calc R
H7C H 0.1148 -0.0198 0.4597 0.086 Uiso 1 1 calc R
N8 N 0.3306(2) 0.0395(4) 0.46739(8) 0.0557(8) Uani 1 1 d .
H8 H 0.3906 0.0267 0.4801 0.067 Uiso 1 1 calc R
N9 N 0.3294(2) 0.0069(4) 0.42823(8) 0.0549(8) Uani 1 1 d .
H9 H 0.3223 -0.0891 0.4202 0.066 Uiso 1 1 calc R
C10 C 0.3397(3) 0.1285(5) 0.40212(10) 0.0456(8) Uani 1 1 d .
O2 O 0.3455(2) 0.2648(3) 0.41115(8) 0.0693(8) Uani 1 1 d .
O11 O 0.3399(2) 0.0708(3) 0.36630(7) 0.0540(7) Uani 1 1 d .
C12 C 0.3566(3) 0.1891(4) 0.33588(10) 0.0546(9) Uani 1 1 d .
H12A H 0.4227 0.2493 0.3409 0.065 Uiso 1 1 calc R
H12B H 0.2952 0.2620 0.3351 0.065 Uiso 1 1 calc R
C13 C 0.4080(3) 0.2000(4) 0.61471(10) 0.0533(9) Uani 1 1 d .
H13A H 0.4662 0.1267 0.6079 0.064 Uiso 1 1 calc R
H13B H 0.3770 0.1655 0.6392 0.064 Uiso 1 1 calc R
C14 C 0.4562(3) 0.3630(4) 0.61985(11) 0.0568(10) Uani 1 1 d .
H14A H 0.4008 0.4335 0.6303 0.068 Uiso 1 1 calc R
H14B H 0.4785 0.4040 0.5948 0.068 Uiso 1 1 calc R
C15 C 0.5540(3) 0.3605(5) 0.64687(14) 0.0795(14) Uani 1 1 d .
H15A H 0.5309 0.3277 0.6723 0.119 Uiso 1 1 calc R
H15B H 0.5853 0.4647 0.6483 0.119 Uiso 1 1 calc R
H15C H 0.6076 0.2873 0.6372 0.119 Uiso 1 1 calc R
C1' C 0.3662(3) 0.1034(4) 0.29827(10) 0.0498(9) Uani 1 1 d .
C2' C 0.4586(3) 0.0162(5) 0.28997(12) 0.0651(11) Uani 1 1 d .
H2' H 0.5144 0.0098 0.3083 0.078 Uiso 1 1 calc R
C3' C 0.4700(4) -0.0613(6) 0.25525(15) 0.0881(15) Uani 1 1 d .
H3' H 0.5321 -0.1220 0.2505 0.106 Uiso 1 1 calc R
C4' C 0.3910(5) -0.0496(7) 0.22799(15) 0.1024(19) Uani 1 1 d .
H4' H 0.3992 -0.1020 0.2044 0.123 Uiso 1 1 calc R
C5' C 0.3000(5) 0.0377(8) 0.23460(15) 0.111(2) Uani 1 1 d .
H5' H 0.2465 0.0463 0.2155 0.133 Uiso 1 1 calc R
C6' C 0.2866(3) 0.1147(6) 0.27015(13) 0.0807(14) Uani 1 1 d .
H6' H 0.2237 0.1739 0.2748 0.097 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
C2 S1 C5 92.36(16)
N3 C2 S2 126.5(3)
N3 C2 S1 110.4(3)
S2 C2 S1 123.1(2)
C2 N3 C4 116.3(3)
C2 N3 C13 122.0(3)
C4 N3 C13 121.7(3)
O1 C4 N3 122.4(3)
O1 C4 C5 126.8(3)
N3 C4 C5 110.8(3)
C6 C5 C4 126.0(3)
C6 C5 S1 123.9(3)
C4 C5 S1 110.1(2)
N8 C6 C5 120.6(3)
N8 C6 C7 118.4(3)
C5 C6 C7 121.0(3)
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C6 N8 N9 122.3(3)
C6 N8 H8 118.8
N9 N8 H8 118.8
C10 N9 N8 119.5(3)
C10 N9 H9 120.2
N8 N9 H9 120.2
O2 C10 O11 126.6(4)
O2 C10 N9 123.8(3)
O11 C10 N9 109.6(3)
C10 O11 C12 114.6(3)
O11 C12 C1' 107.6(3)
O11 C12 H12A 110.2
C1' C12 H12A 110.2
O11 C12 H12B 110.2
C1' C12 H12B 110.2
H12A C12 H12B 108.5
N3 C13 C14 113.4(3)
N3 C13 H13A 108.9
C14 C13 H13A 108.9
N3 C13 H13B 108.9
C14 C13 H13B 108.9
H13A C13 H13B 107.7
C13 C14 C15 111.5(3)
C13 C14 H14A 109.3
C15 C14 H14A 109.3
C13 C14 H14B 109.3
C15 C14 H14B 109.3
H14A C14 H14B 108.0
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C6' C1' C2' 118.1(4)
C6' C1' C12 121.6(4)
C2' C1' C12 120.3(3)
C3' C2' C1' 121.3(4)
C3' C2' H2' 119.4
C1' C2' H2' 119.4
C4' C3' C2' 119.9(5)
C4' C3' H3' 120.0
C2' C3' H3' 120.0
C3' C4' C5' 120.7(5)
C3' C4' H4' 119.6
C5' C4' H4' 119.6
C4' C5' C6' 119.8(5)
C4' C5' H5' 120.1
C6' C5' H5' 120.1
C1' C6' C5' 120.1(4)
C1' C6' H6' 119.9
C5' C6' H6' 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C2 1.724(4)
S1 C5 1.757(3)
C2 N3 1.374(4)
C2 S2 1.644(3)
N3 C4 1.394(4)
N3 C13 1.463(4)
C4 O1 1.236(4)
C4 C5 1.429(5)
C5 C6 1.363(4)
C6 N8 1.339(4)
C6 C7 1.493(5)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
N8 N9 1.376(4)
N8 H8 0.8600
N9 C10 1.369(5)
N9 H9 0.8600
C10 O2 1.193(4)
C10 O11 1.326(4)
O11 C12 1.461(4)
C12 C1' 1.488(5)
C12 H12A 0.9700
C12 H12B 0.9700
C13 C14 1.506(5)
C13 H13A 0.9700
C13 H13B 0.9700
C14 C15 1.514(5)
C14 H14A 0.9700
C14 H14B 0.9700
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C1' C6' 1.375(5)
C1' C2' 1.377(5)
C2' C3' 1.370(6)
C2' H2' 0.9300
C3' C4' 1.350(7)
C3' H3' 0.9300
C4' C5' 1.352(8)
C4' H4' 0.9300
C5' C6' 1.396(7)
C5' H5' 0.9300
C6' H6' 0.9300
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 0.2(3)
C5 S1 C2 S2 -179.6(2)
S2 C2 N3 C4 -179.5(3)
S1 C2 N3 C4 0.8(4)
S2 C2 N3 C13 2.2(5)
S1 C2 N3 C13 -177.5(3)
C2 N3 C4 O1 178.2(3)
C13 N3 C4 O1 -3.5(5)
C2 N3 C4 C5 -1.5(4)
C13 N3 C4 C5 176.8(3)
O1 C4 C5 C6 2.9(6)
N3 C4 C5 C6 -177.4(3)
O1 C4 C5 S1 -178.2(3)
N3 C4 C5 S1 1.5(4)
C2 S1 C5 C6 177.9(3)
C2 S1 C5 C4 -1.0(3)
C4 C5 C6 N8 0.6(6)
S1 C5 C6 N8 -178.1(3)
C4 C5 C6 C7 178.8(3)
S1 C5 C6 C7 0.1(5)
C5 C6 N8 N9 -172.3(3)
C7 C6 N8 N9 9.5(5)
C6 N8 N9 C10 81.6(4)
N8 N9 C10 O2 -3.0(5)
N8 N9 C10 O11 178.1(3)
O2 C10 O11 C12 4.4(5)
N9 C10 O11 C12 -176.7(3)
C10 O11 C12 C1' 174.2(3)
C2 N3 C13 C14 -84.9(4)
C4 N3 C13 C14 96.9(4)
N3 C13 C14 C15 -172.0(3)
O11 C12 C1' C6' 111.3(4)
O11 C12 C1' C2' -72.0(4)
C6' C1' C2' C3' -2.0(6)
C12 C1' C2' C3' -178.8(4)
C1' C2' C3' C4' 1.8(7)
C2' C3' C4' C5' -0.3(8)
C3' C4' C5' C6' -0.9(9)
C2' C1' C6' C5' 0.8(7)
C12 C1' C6' C5' 177.6(4)
C4' C5' C6' C1' 0.7(8)
