#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/04/2240466.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_2240466
loop_
_publ_author_name
'de Oliveira, Adriano Bof'
'Lira de Farias, Renan'
'Näther, Christian'
'Jess, Inke'
_publ_section_title
;
 Crystal structure of
 (E)-2-[1-(1,3-benzodioxol-5-yl)ethylidene]-N-ethylhydrazine-1-carbothioamide
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o208
_journal_page_last               o209
_journal_paper_doi               10.1107/S2056989015003837
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C12 H15 N3 O2 S'
_chemical_formula_moiety         'C12 H15 N3 O2 S'
_chemical_formula_sum            'C12 H15 N3 O2 S'
_chemical_formula_weight         265.33
_chemical_name_systematic
(E)-2-[1-(Benzo[d][1,3]dioxol-5-yl)ethylidene]-N-ethylhydrazine-1-carbothioamide
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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-2013
_cell_angle_alpha                83.908(5)
_cell_angle_beta                 79.913(5)
_cell_angle_gamma                87.029(5)
_cell_formula_units_Z            2
_cell_length_a                   5.7207(3)
_cell_length_b                   10.6225(6)
_cell_length_c                   10.8103(6)
_cell_measurement_reflns_used    9389
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      1.92
_cell_volume                     642.74(6)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2008)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2008)
;
_computing_data_reduction
;
X-RED32 (Stoe & Cie, 2008)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2013-2 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      250(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Stoe IPDS-1'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9389
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_min         1.923
_exptl_absorpt_coefficient_mu    0.25
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.230
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2811
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0649P)²+0.1118P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1163
_reflns_number_gt                2288
_reflns_number_total             2811
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5837sup1.cif
_cod_data_source_block           I
_cod_database_code               2240466
_cod_database_fobs_code          2240466
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           20.13
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.7435(3) 0.18956(14) 0.16339(15) 0.0407(3) Uani d 1 . .
C C2 0.8619(3) 0.24715(14) 0.24537(15) 0.0428(3) Uani d 1 . .
H H2 0.8352 0.3334 0.2575 0.051 Uiso calc 1 . .
C C3 1.0167(3) 0.17309(16) 0.30646(16) 0.0457(4) Uani d 1 . .
C C4 1.0618(3) 0.04644(16) 0.28893(17) 0.0516(4) Uani d 1 . .
C C5 0.9543(4) -0.01187(16) 0.20857(19) 0.0581(5) Uani d 1 . .
H H5 0.9863 -0.0977 0.1962 0.070 Uiso calc 1 . .
C C6 0.7937(3) 0.06224(16) 0.14522(17) 0.0515(4) Uani d 1 . .
H H6 0.7174 0.0250 0.0887 0.062 Uiso calc 1 . .
O O1 1.1441(2) 0.20752(13) 0.39317(13) 0.0621(4) Uani d 1 . .
C C7 1.2882(3) 0.0980(2) 0.4229(2) 0.0615(5) Uani d 1 . .
H H7A 1.4562 0.1148 0.3917 0.074 Uiso calc 1 . .
H H7B 1.2668 0.0771 0.5146 0.074 Uiso calc 1 . .
O O2 1.2191(3) -0.00457(13) 0.36476(15) 0.0698(4) Uani d 1 . .
C C8 0.5558(3) 0.26302(14) 0.10543(15) 0.0407(3) Uani d 1 . .
C C9 0.4637(3) 0.21798(17) -0.00254(18) 0.0541(4) Uani d 1 . .
H H9A 0.3116 0.1794 0.0280 0.081 Uiso calc 1 . .
H H9B 0.5755 0.1560 -0.0415 0.081 Uiso calc 1 . .
H H9C 0.4440 0.2892 -0.0643 0.081 Uiso calc 1 . .
N N1 0.4771(2) 0.36261(12) 0.15902(13) 0.0420(3) Uani d 1 . .
N N2 0.2949(2) 0.43540(12) 0.11811(13) 0.0432(3) Uani d 1 . .
H H1N2 0.2234 0.4229 0.0560 0.052 Uiso d 1 . .
C C10 0.2019(3) 0.53176(15) 0.18658(16) 0.0461(4) Uani d 1 . .
S S1 -0.03625(8) 0.61725(4) 0.15015(5) 0.05451(17) Uani d 1 . .
N N3 0.3122(3) 0.55269(18) 0.27906(18) 0.0732(5) Uani d 1 . .
H H1N3 0.4362 0.5027 0.2843 0.088 Uiso d 1 A .
C C11 0.2171(16) 0.6290(8) 0.3858(8) 0.071(2) Uani d 0.5 A 1
H H11A 0.1138 0.6987 0.3576 0.085 Uiso calc 0.5 A 1
H H11B 0.1232 0.5758 0.4544 0.085 Uiso calc 0.5 A 1
C C11' 0.2731(18) 0.6716(7) 0.3447(8) 0.0675(19) Uani d 0.5 A 2
H H11C 0.2989 0.7447 0.2812 0.081 Uiso calc 0.5 A 2
H H11D 0.1073 0.6766 0.3872 0.081 Uiso calc 0.5 A 2
C C12 0.4155(6) 0.6790(3) 0.4304(3) 0.1149(12) Uani d 1 . .
H H12A 0.5616 0.6353 0.3959 0.172 Uiso calc 0.5 A 1
H H12B 0.3914 0.6663 0.5219 0.172 Uiso calc 0.5 A 1
H H12C 0.4259 0.7689 0.4032 0.172 Uiso calc 0.5 A 1
H H12D 0.4978 0.5980 0.4444 0.172 Uiso calc 0.5 A 2
H H12E 0.3205 0.7007 0.5092 0.172 Uiso calc 0.5 A 2
H H12F 0.5307 0.7438 0.3993 0.172 Uiso calc 0.5 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
C6 C1 C2 119.34(15)
C6 C1 C8 121.30(15)
C2 C1 C8 119.22(13)
C3 C2 C1 117.54(14)
C3 C2 H2 121.2
C1 C2 H2 121.2
C2 C3 O1 127.54(15)
C2 C3 C4 122.40(16)
O1 C3 C4 110.05(15)
C5 C4 O2 128.69(16)
C5 C4 C3 121.73(16)
O2 C4 C3 109.57(17)
C4 C5 C6 116.86(15)
C4 C5 H5 121.6
C6 C5 H5 121.6
C1 C6 C5 122.10(17)
C1 C6 H6 118.9
C5 C6 H6 118.9
C3 O1 C7 105.38(14)
O2 C7 O1 108.49(15)
O2 C7 H7A 110.0
O1 C7 H7A 110.0
O2 C7 H7B 110.0
O1 C7 H7B 110.0
H7A C7 H7B 108.4
C4 O2 C7 105.90(14)
N1 C8 C1 114.42(14)
N1 C8 C9 124.48(15)
C1 C8 C9 121.04(13)
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C8 N1 N2 120.07(14)
C10 N2 N1 117.50(13)
C10 N2 H1N2 115.4
N1 N2 H1N2 126.9
N3 C10 N2 115.66(15)
N3 C10 S1 123.92(12)
N2 C10 S1 120.41(13)
C10 N3 C11 126.2(4)
C10 N3 C11' 123.1(4)
C10 N3 H1N3 113.3
C11 N3 H1N3 119.0
C11' N3 H1N3 121.5
C12 C11 N3 108.7(6)
C12 C11 H11A 110.0
N3 C11 H11A 110.0
C12 C11 H11B 110.0
N3 C11 H11B 110.0
H11A C11 H11B 108.3
C12 C11' N3 114.0(6)
C12 C11' H11C 108.7
N3 C11' H11C 108.7
C12 C11' H11D 108.7
N3 C11' H11D 108.7
H11C C11' H11D 107.6
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C11' C12 H12D 109.5
C11' C12 H12E 109.5
H12D C12 H12E 109.5
C11' C12 H12F 109.5
H12D C12 H12F 109.5
H12E C12 H12F 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.395(2)
C1 C2 1.410(2)
C1 C8 1.483(2)
C2 C3 1.364(2)
C2 H2 0.9400
C3 O1 1.372(2)
C3 C4 1.383(2)
C4 C5 1.363(3)
C4 O2 1.375(2)
C5 C6 1.401(3)
C5 H5 0.9400
C6 H6 0.9400
O1 C7 1.432(2)
C7 O2 1.420(3)
C7 H7A 0.9800
C7 H7B 0.9800
C8 N1 1.2832(19)
C8 C9 1.493(2)
C9 H9A 0.9700
C9 H9B 0.9700
C9 H9C 0.9700
N1 N2 1.3730(18)
N2 C10 1.358(2)
N2 H1N2 0.8699
C10 N3 1.315(2)
C10 S1 1.6792(17)
N3 C11 1.489(9)
N3 C11' 1.501(9)
N3 H1N3 0.8700
C11 C12 1.453(10)
C11 H11A 0.9800
C11 H11B 0.9800
C11' C12 1.347(10)
C11' H11C 0.9800
C11' H11D 0.9800
C12 H12A 0.9700
C12 H12B 0.9700
C12 H12C 0.9700
C12 H12D 0.9700
C12 H12E 0.9700
C12 H12F 0.9700
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 H1N2 S1 2_565 0.87 2.72 3.5842(14) 175.2
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
C6 C1 C2 C3 -1.9(2)
C8 C1 C2 C3 173.75(14)
C1 C2 C3 O1 -177.54(15)
C1 C2 C3 C4 1.0(2)
C2 C3 C4 C5 0.3(3)
O1 C3 C4 C5 179.06(16)
C2 C3 C4 O2 -178.38(15)
O1 C3 C4 O2 0.34(19)
O2 C4 C5 C6 177.85(17)
C3 C4 C5 C6 -0.6(3)
C2 C1 C6 C5 1.7(3)
C8 C1 C6 C5 -173.86(16)
C4 C5 C6 C1 -0.4(3)
C2 C3 O1 C7 -176.90(16)
C4 C3 O1 C7 4.46(18)
C3 O1 C7 O2 -7.55(19)
C5 C4 O2 C7 176.35(19)
C3 C4 O2 C7 -5.04(19)
O1 C7 O2 C4 7.8(2)
C6 C1 C8 N1 159.25(15)
C2 C1 C8 N1 -16.3(2)
C6 C1 C8 C9 -18.1(2)
C2 C1 C8 C9 166.30(15)
C1 C8 N1 N2 -176.84(12)
C9 C8 N1 N2 0.4(2)
C8 N1 N2 C10 173.15(14)
N1 N2 C10 N3 6.2(2)
N1 N2 C10 S1 -174.75(11)
N2 C10 N3 C11 -164.2(4)
S1 C10 N3 C11 16.8(5)
N2 C10 N3 C11' 165.3(4)
S1 C10 N3 C11' -13.8(5)
C10 N3 C11 C12 -153.3(4)
C11' N3 C11 C12 -61.3(15)
C10 N3 C11' C12 -175.3(4)
C11 N3 C11' C12 79.0(15)
N3 C11' C12 C11 -73.0(13)
N3 C11 C12 C11' 68.3(14)
