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Searches for new tuberculostatic agents are important considering the occurrence of drug-resistant strains of Mycobacterium tuberculosis. The structures of three new potentially tuberculostatic compounds, namely isopropyl methyl (2-hy­droxy­benzo­yl)carbonohydrazonodi­thio­ate, C12H16N2O2S2, (Z)-benzyl methyl (2-hy­droxy­benzo­yl)carbonohydrazonodi­thio­ate, C16H16N2O2S2, and dibenzyl (2-hy­droxy­benzo­yl)carbonohydrazonodi­thio­ate propan-2-ol mono­solvate, C22H20N2O2S2·C3H8O, were determined by X-ray diffraction. The mutual orientation of the three main fragments of the compounds, namely an aromatic ring, a di­thio­ester group and a hydrazide group, can influence the biological activity of the compounds. In all three of the structures studied, the C(=O)NH group is in the anti conformation. In addition, the presence of the hy­droxy group in the ortho position of the aromatic ring in all three structures leads to the formation of an intra­molecular hydrogen bond stabilizing the planarity of the mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616020556/fn3226sup1.cif
Contains datablocks H1, H2, H3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616020556/fn3226H1sup2.hkl
Contains datablock H1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616020556/fn3226H2sup3.hkl
Contains datablock H2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616020556/fn3226H3sup4.hkl
Contains datablock H3

CCDC references: 1524668; 1524667; 1524666

Computing details top

For all compounds, data collection: APEX2 (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008a). Program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015) for H1; SHELXL97 (Sheldrick, 2008a) for H2, H3. For all compounds, molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006). Software used to prepare material for publication: PLATON (Spek, 2009), publCIF (Westrip, 2010) for H1; PLATON (Spek, 2009) for H2, H3.

(H1) (2-Hydroxybenzoyl)carbonohydrazonodithioate top
Crystal data top
C12H16N2O2S2Dx = 1.315 Mg m3
Mr = 284.39Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pna21Cell parameters from 9640 reflections
a = 12.8212 (5) Åθ = 4.2–70.6°
b = 10.5085 (4) ŵ = 3.34 mm1
c = 10.6608 (5) ÅT = 293 K
V = 1436.35 (10) Å3Block, colourless
Z = 40.9 × 0.2 × 0.2 mm
F(000) = 600
Data collection top
Bruker SMART APEXII CCD
diffractometer
2688 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
ω scanθmax = 70.8°, θmin = 5.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1514
Tmin = 0.347, Tmax = 0.753k = 1212
15904 measured reflectionsl = 1212
2705 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.029 w = 1/[σ2(Fo2) + (0.0507P)2 + 0.1855P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.081(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.19 e Å3
2705 reflectionsΔρmin = 0.23 e Å3
178 parametersAbsolute structure: Refined as an inversion twin.
1 restraintAbsolute structure parameter: 0.12 (2)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.5649 (2)0.0333 (2)0.0188 (3)0.0463 (5)
C40.51569 (17)0.3097 (2)0.1828 (2)0.0403 (4)
C110.4970 (2)0.2228 (3)0.0545 (3)0.0604 (7)
H110.52380.22870.03140.072*
C120.3955 (3)0.2975 (3)0.0636 (4)0.0775 (9)
H12A0.40930.38620.04960.116*
H12B0.34740.26710.00150.116*
H12C0.36590.28640.14560.116*
C130.5782 (4)0.2704 (5)0.1436 (6)0.1068 (17)
H13A0.55360.26100.22810.160*
H13B0.64110.22220.13280.160*
H13C0.59190.35860.12690.160*
C210.7370 (3)0.0840 (4)0.1270 (4)0.0827 (11)
H21A0.69540.15310.15820.124*
H21B0.78330.05520.19180.124*
H21C0.77690.11240.05620.124*
C410.42548 (18)0.3731 (2)0.2449 (2)0.0399 (5)
C420.4488 (2)0.4766 (3)0.3224 (3)0.0511 (6)
H420.51820.50000.33320.061*
C430.3726 (3)0.5448 (3)0.3832 (3)0.0645 (8)
H430.39040.61300.43440.077*
C440.2698 (3)0.5112 (3)0.3673 (3)0.0642 (7)
H440.21780.55780.40700.077*
C450.2433 (2)0.4085 (3)0.2928 (3)0.0574 (6)
H450.17360.38600.28350.069*
C460.32026 (18)0.3383 (2)0.2315 (2)0.0423 (5)
N20.57494 (15)0.15203 (19)0.0424 (2)0.0490 (5)
N30.49568 (16)0.20479 (19)0.1147 (2)0.0473 (5)
H30.43470.17080.11580.057*
O40.60509 (13)0.35168 (18)0.1945 (2)0.0556 (5)
O460.29514 (12)0.23761 (18)0.1576 (2)0.0534 (4)
H460.23440.21710.17050.080*
S1A0.4675 (5)0.0580 (3)0.0899 (4)0.0572 (10)0.67 (2)
S1B0.4509 (7)0.0583 (9)0.0534 (19)0.080 (3)0.33 (2)
S20.65384 (6)0.04348 (7)0.08043 (12)0.0631 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0410 (11)0.0445 (12)0.0535 (13)0.0061 (9)0.0012 (10)0.0015 (10)
C40.0360 (10)0.0352 (10)0.0496 (11)0.0000 (8)0.0013 (9)0.0062 (9)
C110.0702 (16)0.0436 (13)0.0673 (16)0.0016 (12)0.0036 (14)0.0014 (12)
C120.083 (2)0.0596 (17)0.090 (2)0.0188 (15)0.0050 (19)0.0004 (16)
C130.082 (3)0.096 (3)0.142 (4)0.007 (2)0.020 (3)0.047 (3)
C210.071 (2)0.080 (2)0.096 (2)0.0040 (18)0.0401 (19)0.0049 (19)
C410.0420 (11)0.0339 (10)0.0437 (11)0.0003 (9)0.0003 (9)0.0025 (9)
C420.0530 (13)0.0440 (12)0.0561 (13)0.0046 (11)0.0027 (11)0.0032 (11)
C430.082 (2)0.0513 (15)0.0603 (16)0.0019 (13)0.0036 (14)0.0186 (12)
C440.0685 (17)0.0564 (16)0.0676 (16)0.0086 (14)0.0165 (14)0.0155 (13)
C450.0448 (13)0.0600 (14)0.0673 (15)0.0041 (12)0.0083 (11)0.0064 (14)
C460.0405 (11)0.0391 (11)0.0472 (11)0.0036 (9)0.0020 (9)0.0008 (9)
N20.0384 (9)0.0435 (10)0.0649 (12)0.0046 (7)0.0088 (9)0.0023 (9)
N30.0338 (9)0.0408 (10)0.0672 (12)0.0003 (7)0.0071 (8)0.0077 (9)
O40.0350 (8)0.0511 (10)0.0807 (13)0.0031 (7)0.0003 (8)0.0072 (9)
O460.0320 (7)0.0546 (10)0.0736 (10)0.0004 (7)0.0015 (8)0.0186 (9)
S1A0.0505 (16)0.0415 (8)0.0794 (18)0.0032 (9)0.0222 (12)0.0042 (8)
S1B0.0432 (18)0.052 (2)0.146 (7)0.0021 (11)0.010 (3)0.022 (3)
S20.0638 (4)0.0546 (4)0.0709 (4)0.0131 (3)0.0199 (3)0.0048 (3)
Geometric parameters (Å, º) top
C1—N21.280 (3)C21—S21.782 (4)
C1—S1A1.747 (4)C21—H21A0.9600
C1—S21.752 (3)C21—H21B0.9600
C1—S1B1.789 (9)C21—H21C0.9600
C4—O41.234 (3)C41—C421.397 (4)
C4—N31.345 (3)C41—C461.405 (3)
C4—C411.490 (3)C42—C431.374 (4)
C11—C131.495 (5)C42—H420.9300
C11—C121.522 (4)C43—C441.375 (5)
C11—S1A1.813 (4)C43—H430.9300
C11—S1B1.827 (10)C44—C451.383 (4)
C11—H110.9800C44—H440.9300
C12—H12A0.9600C45—C461.395 (3)
C12—H12B0.9600C45—H450.9300
C12—H12C0.9600C46—O461.358 (3)
C13—H13A0.9600N2—N31.390 (3)
C13—H13B0.9600N3—H30.8600
C13—H13C0.9600O46—H460.8200
N2—C1—S1A121.4 (2)H21A—C21—H21B109.5
N2—C1—S2120.2 (2)S2—C21—H21C109.5
S1A—C1—S2118.32 (18)H21A—C21—H21C109.5
N2—C1—S1B124.5 (4)H21B—C21—H21C109.5
S2—C1—S1B114.1 (4)C42—C41—C46117.9 (2)
O4—C4—N3121.6 (2)C42—C41—C4116.4 (2)
O4—C4—C41121.1 (2)C46—C41—C4125.7 (2)
N3—C4—C41117.29 (19)C43—C42—C41122.2 (3)
C13—C11—C12112.4 (3)C43—C42—H42118.9
C13—C11—S1A109.4 (4)C41—C42—H42118.9
C12—C11—S1A107.6 (3)C42—C43—C44119.3 (3)
C13—C11—S1B123.1 (6)C42—C43—H43120.3
C12—C11—S1B102.2 (3)C44—C43—H43120.3
C13—C11—H11109.1C43—C44—C45120.5 (3)
C12—C11—H11109.1C43—C44—H44119.8
S1A—C11—H11109.1C45—C44—H44119.8
C11—C12—H12A109.5C44—C45—C46120.5 (3)
C11—C12—H12B109.5C44—C45—H45119.7
H12A—C12—H12B109.5C46—C45—H45119.7
C11—C12—H12C109.5O46—C46—C45121.1 (2)
H12A—C12—H12C109.5O46—C46—C41119.3 (2)
H12B—C12—H12C109.5C45—C46—C41119.6 (2)
C11—C13—H13A109.5C1—N2—N3115.1 (2)
C11—C13—H13B109.5C4—N3—N2119.11 (19)
H13A—C13—H13B109.5C4—N3—H3120.4
C11—C13—H13C109.5N2—N3—H3120.4
H13A—C13—H13C109.5C46—O46—H46109.5
H13B—C13—H13C109.5C1—S1A—C11106.6 (2)
S2—C21—H21A109.5C1—S1B—C11104.2 (4)
S2—C21—H21B109.5C1—S2—C21102.21 (15)
O4—C4—C41—C423.8 (3)S2—C1—N2—N3175.43 (18)
N3—C4—C41—C42175.6 (2)S1B—C1—N2—N38.9 (9)
O4—C4—C41—C46175.7 (2)O4—C4—N3—N28.6 (3)
N3—C4—C41—C464.9 (3)C41—C4—N3—N2172.0 (2)
C46—C41—C42—C430.9 (4)C1—N2—N3—C4155.3 (2)
C4—C41—C42—C43178.7 (2)N2—C1—S1A—C11169.2 (3)
C41—C42—C43—C440.3 (5)S2—C1—S1A—C117.5 (5)
C42—C43—C44—C451.1 (5)C13—C11—S1A—C181.5 (4)
C43—C44—C45—C460.7 (5)C12—C11—S1A—C1156.1 (3)
C44—C45—C46—O46179.7 (3)N2—C1—S1B—C11159.8 (5)
C44—C45—C46—C410.5 (4)S2—C1—S1B—C1132.9 (11)
C42—C41—C46—O46179.5 (2)C13—C11—S1B—C161.1 (12)
C4—C41—C46—O461.0 (3)C12—C11—S1B—C1171.5 (8)
C42—C41—C46—C451.2 (4)N2—C1—S2—C212.3 (3)
C4—C41—C46—C45178.3 (2)S1A—C1—S2—C21179.1 (3)
S1A—C1—N2—N37.9 (4)S1B—C1—S2—C21165.6 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O46—H46···O4i0.821.832.640 (2)172
N3—H3···O460.861.972.634 (2)133
C13—H13B···S20.962.953.511 (5)118
C11—H11···S20.982.623.109 (3)111
Symmetry code: (i) x1/2, y+1/2, z.
(H2) (Z)-Benzyl methyl (2-hydroxybenzoyl)carbonohydrazonodithioate top
Crystal data top
C16H16N2O2S2F(000) = 696
Mr = 332.43Dx = 1.367 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 13.2762 (2) ÅCell parameters from 9883 reflections
b = 12.6138 (2) Åθ = 3.5–70.5°
c = 10.1742 (2) ŵ = 3.06 mm1
β = 108.5970 (9)°T = 293 K
V = 1614.84 (5) Å3Plate, colourless
Z = 41.00 × 0.30 × 0.04 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
2931 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.040
ω scanθmax = 70.6°, θmin = 3.5°
Absorption correction: multi-scan
(TWINABS; Sheldrick, 2008b)
h = 1615
Tmin = 0.567, Tmax = 0.753k = 015
32181 measured reflectionsl = 012
3055 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.104 w = 1/[σ2(Fo2) + (0.0645P)2 + 0.2643P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
3055 reflectionsΔρmax = 0.31 e Å3
202 parametersΔρmin = 0.31 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin.

Statistics for all single and composite reflections —————————————————

Scan 2-theta R(int) Incid. factors Diffr. factors K Total I>2sig(I) 1 -35.0 0.0348 6.159 -12.430 0.892 - 1.172 0.829 1181 1063 2 -35.0 0.0341 5.755 - 8.396 0.897 - 1.170 0.763 1390 1287 3 -35.0 0.0369 3.224 - 6.474 0.913 - 1.176 0.915 1316 1216 4 -70.0 0.0557 0.727 - 1.132 0.890 - 1.176 1.117 2139 1912 5 -70.0 0.0401 0.809 - 1.984 0.912 - 1.176 0.971 1841 1641 6 -70.0 0.0337 0.940 - 1.927 0.892 - 1.156 0.780 1787 1562 7 -70.0 0.0352 0.888 - 1.314 0.891 - 1.154 0.745 1949 1821 8 -70.0 0.0305 0.673 - 0.953 0.891 - 1.176 0.711 1961 1835 9 -70.0 0.0375 0.537 - 0.988 0.912 - 1.176 0.810 1868 1723 10 -110.0 0.0545 0.125 - 0.333 0.909 - 1.176 1.018 1865 1564 11 -110.0 0.0416 0.131 - 0.279 0.908 - 1.176 0.859 1833 1582 12 -110.0 0.0349 0.174 - 0.355 0.894 - 1.158 0.747 1874 1557 13 -110.0 0.0341 0.133 - 0.230 0.892 - 1.155 0.708 1850 1634 14 -110.0 0.0344 0.130 - 0.188 0.891 - 1.166 0.686 1796 1639 15 -110.0 0.0367 0.192 - 0.269 0.891 - 1.176 0.687 1840 1648 16 -110.0 0.0425 0.206 - 0.359 0.909 - 1.176 0.815 1810 1587 17 -110.0 0.0512 0.174 - 0.356 0.906 - 1.176 0.993 1849 1581

All scans 0.0374 0.125 -12.430 0.890 - 1.176 0.833 30149 26852

su = K * Sqrt[ sigma2(I) + (g<I>)2 ] where sigma(I) is estimated by SAINT

The above statistics are based on all non-rejected data, ignoring reflections without equivalents when estimating R(int) and K.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.25504 (12)0.77077 (14)0.09649 (17)0.0436 (4)
C40.07133 (13)0.84530 (13)0.26026 (19)0.0429 (4)
C110.35229 (19)0.59595 (17)0.0138 (3)0.0677 (6)
H11A0.32230.61930.08160.081*
H11B0.42020.63110.05400.081*
C120.36823 (14)0.47773 (15)0.0178 (2)0.0515 (4)
C130.43092 (16)0.42485 (19)0.1348 (2)0.0647 (5)
H130.46150.46190.21690.078*
C140.44807 (18)0.3165 (2)0.1294 (3)0.0775 (7)
H140.49010.28090.20770.093*
C150.40272 (18)0.26240 (19)0.0079 (3)0.0781 (7)
H150.41490.19010.00370.094*
C160.34046 (19)0.3136 (2)0.1057 (3)0.0738 (7)
H160.30950.27600.18730.089*
C170.32243 (16)0.42093 (18)0.1017 (2)0.0608 (5)
H170.27900.45520.18040.073*
C210.2886 (2)0.96643 (17)0.0016 (3)0.0731 (6)
H21A0.21270.96870.04240.110*
H21B0.32091.00730.05700.110*
H21C0.30840.99540.09040.110*
C410.00117 (12)0.79433 (13)0.33090 (18)0.0420 (4)
C420.05349 (15)0.86329 (15)0.3924 (2)0.0519 (4)
H420.04390.93600.38720.062*
C430.12076 (16)0.82651 (17)0.4602 (2)0.0588 (5)
H430.15650.87380.49970.071*
C440.13501 (15)0.71880 (16)0.4693 (2)0.0560 (5)
H440.18020.69350.51560.067*
C450.08279 (14)0.64853 (15)0.4102 (2)0.0492 (4)
H450.09290.57600.41690.059*
C460.01471 (12)0.68559 (14)0.34047 (17)0.0406 (3)
N20.19609 (11)0.82948 (11)0.14342 (16)0.0453 (3)
N30.13186 (10)0.78164 (10)0.20946 (15)0.0430 (3)
H30.13050.71390.21790.052*
O40.07656 (11)0.94196 (10)0.25163 (16)0.0611 (4)
O460.03793 (10)0.61603 (9)0.28344 (15)0.0507 (3)
H460.00890.55790.27490.076*
S10.26284 (4)0.63121 (4)0.11120 (6)0.05753 (17)
S20.33320 (4)0.83151 (4)0.00634 (6)0.05742 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0431 (7)0.0463 (9)0.0474 (8)0.0026 (6)0.0229 (7)0.0036 (7)
C40.0440 (8)0.0381 (8)0.0516 (9)0.0018 (6)0.0224 (7)0.0021 (7)
C110.0753 (13)0.0578 (11)0.0929 (16)0.0068 (10)0.0591 (13)0.0001 (11)
C120.0451 (8)0.0518 (10)0.0699 (11)0.0034 (7)0.0358 (8)0.0022 (9)
C130.0546 (10)0.0798 (14)0.0619 (12)0.0012 (10)0.0219 (9)0.0037 (10)
C140.0601 (12)0.0808 (16)0.1001 (19)0.0161 (11)0.0374 (13)0.0339 (15)
C150.0650 (12)0.0520 (12)0.138 (2)0.0003 (10)0.0620 (15)0.0053 (14)
C160.0639 (12)0.0810 (15)0.0915 (17)0.0113 (12)0.0459 (12)0.0285 (14)
C170.0523 (10)0.0783 (14)0.0603 (11)0.0060 (9)0.0298 (9)0.0014 (10)
C210.0929 (16)0.0491 (11)0.0975 (17)0.0121 (11)0.0587 (14)0.0036 (11)
C410.0400 (8)0.0443 (9)0.0466 (9)0.0020 (6)0.0209 (7)0.0036 (7)
C420.0557 (10)0.0449 (9)0.0647 (11)0.0058 (8)0.0327 (9)0.0053 (8)
C430.0578 (10)0.0639 (12)0.0671 (12)0.0097 (9)0.0375 (10)0.0080 (10)
C440.0492 (9)0.0676 (12)0.0620 (11)0.0025 (8)0.0330 (8)0.0017 (9)
C450.0469 (9)0.0513 (9)0.0565 (10)0.0042 (7)0.0266 (8)0.0013 (8)
C460.0388 (7)0.0420 (8)0.0456 (9)0.0009 (6)0.0199 (7)0.0025 (7)
N20.0464 (7)0.0440 (7)0.0541 (8)0.0035 (6)0.0281 (7)0.0019 (6)
N30.0470 (7)0.0351 (7)0.0565 (8)0.0007 (5)0.0302 (6)0.0009 (6)
O40.0730 (8)0.0362 (7)0.0923 (10)0.0039 (6)0.0518 (8)0.0013 (6)
O460.0561 (7)0.0379 (6)0.0729 (9)0.0018 (5)0.0413 (6)0.0052 (6)
S10.0727 (3)0.0465 (3)0.0735 (3)0.0054 (2)0.0517 (3)0.0009 (2)
S20.0619 (3)0.0552 (3)0.0717 (3)0.0051 (2)0.0446 (3)0.0011 (2)
Geometric parameters (Å, º) top
C1—N21.276 (2)C17—H170.9300
C1—S21.7641 (16)C21—S21.795 (2)
C1—S11.7669 (18)C21—H21A0.9600
C4—O41.226 (2)C21—H21B0.9600
C4—N31.350 (2)C21—H21C0.9600
C4—C411.491 (2)C41—C461.396 (2)
C11—C121.505 (3)C41—C421.402 (2)
C11—S11.8276 (19)C42—C431.371 (3)
C11—H11A0.9700C42—H420.9300
C11—H11B0.9700C43—C441.379 (3)
C12—C171.375 (3)C43—H430.9300
C12—C131.387 (3)C44—C451.376 (3)
C13—C141.389 (4)C44—H440.9300
C13—H130.9300C45—C461.396 (2)
C14—C151.372 (4)C45—H450.9300
C14—H140.9300C46—O461.3615 (19)
C15—C161.352 (4)N2—N31.3813 (18)
C15—H150.9300N3—H30.8600
C16—C171.378 (3)O46—H460.8200
C16—H160.9300
N2—C1—S2118.38 (13)S2—C21—H21B109.5
N2—C1—S1124.96 (13)H21A—C21—H21B109.5
S2—C1—S1116.65 (9)S2—C21—H21C109.5
O4—C4—N3120.66 (16)H21A—C21—H21C109.5
O4—C4—C41121.44 (15)H21B—C21—H21C109.5
N3—C4—C41117.87 (14)C46—C41—C42117.86 (16)
C12—C11—S1109.67 (14)C46—C41—C4126.06 (14)
C12—C11—H11A109.7C42—C41—C4116.07 (15)
S1—C11—H11A109.7C43—C42—C41121.83 (17)
C12—C11—H11B109.7C43—C42—H42119.1
S1—C11—H11B109.7C41—C42—H42119.1
H11A—C11—H11B108.2C42—C43—C44119.49 (17)
C17—C12—C13118.93 (19)C42—C43—H43120.3
C17—C12—C11118.3 (2)C44—C43—H43120.3
C13—C12—C11122.7 (2)C45—C44—C43120.44 (17)
C12—C13—C14120.0 (2)C45—C44—H44119.8
C12—C13—H13120.0C43—C44—H44119.8
C14—C13—H13120.0C44—C45—C46120.29 (17)
C15—C14—C13119.7 (2)C44—C45—H45119.9
C15—C14—H14120.2C46—C45—H45119.9
C13—C14—H14120.2O46—C46—C41119.61 (14)
C16—C15—C14120.4 (2)O46—C46—C45120.30 (15)
C16—C15—H15119.8C41—C46—C45120.08 (15)
C14—C15—H15119.8C1—N2—N3118.43 (14)
C15—C16—C17120.6 (2)C4—N3—N2117.48 (13)
C15—C16—H16119.7C4—N3—H3121.3
C17—C16—H16119.7N2—N3—H3121.3
C12—C17—C16120.4 (2)C46—O46—H46109.5
C12—C17—H17119.8C1—S1—C11103.13 (9)
C16—C17—H17119.8C1—S2—C21101.24 (9)
S2—C21—H21A109.5
S1—C11—C12—C17108.74 (18)C43—C44—C45—C460.0 (3)
S1—C11—C12—C1374.3 (2)C42—C41—C46—O46179.22 (17)
C17—C12—C13—C141.1 (3)C4—C41—C46—O461.0 (3)
C11—C12—C13—C14175.86 (19)C42—C41—C46—C450.3 (3)
C12—C13—C14—C150.0 (3)C4—C41—C46—C45179.87 (16)
C13—C14—C15—C160.8 (3)C44—C45—C46—O46179.23 (17)
C14—C15—C16—C170.6 (3)C44—C45—C46—C410.3 (3)
C13—C12—C17—C161.3 (3)S2—C1—N2—N3177.60 (12)
C11—C12—C17—C16175.75 (18)S1—C1—N2—N30.9 (2)
C15—C16—C17—C120.5 (3)O4—C4—N3—N22.4 (3)
O4—C4—C41—C46176.59 (18)C41—C4—N3—N2179.59 (14)
N3—C4—C41—C465.4 (3)C1—N2—N3—C4178.99 (16)
O4—C4—C41—C423.2 (3)N2—C1—S1—C11176.14 (17)
N3—C4—C41—C42174.76 (17)S2—C1—S1—C112.39 (14)
C46—C41—C42—C430.0 (3)C12—C11—S1—C1179.41 (16)
C4—C41—C42—C43179.77 (18)N2—C1—S2—C215.47 (17)
C41—C42—C43—C440.4 (3)S1—C1—S2—C21173.16 (12)
C42—C43—C44—C450.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O46—H46···O4i0.821.822.6293 (17)170
N3—H3···O460.862.002.6616 (17)133
C45—H45···O4i0.932.473.098 (2)125
C21—H21A···O46ii0.962.653.507 (3)148
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x, y+3/2, z1/2.
(H3) Dibenzyl (2-hydroxybenzoyl)carbonohydrazonodithioate propan-2-ol monosolvate top
Crystal data top
C22H20N2O2S2·C3H8OZ = 2
Mr = 468.61F(000) = 496
Triclinic, P1Dx = 1.309 Mg m3
a = 8.7950 (18) ÅCu Kα radiation, λ = 1.54178 Å
b = 10.254 (2) ÅCell parameters from 9800 reflections
c = 14.044 (3) Åθ = 3.4–72.3°
α = 74.95 (3)°µ = 2.26 mm1
β = 76.74 (3)°T = 100 K
γ = 88.99 (3)°Block, colourless
V = 1189.3 (5) Å30.42 × 0.18 × 0.16 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
4606 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.036
ω scanθmax = 72.6°, θmin = 3.4°
Absorption correction: multi-scan
(TWINABS; Sheldrick, 2008b)
h = 1010
Tmin = 0.450, Tmax = 0.713k = 1212
33855 measured reflectionsl = 017
4709 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.128 w = 1/[σ2(Fo2) + (0.067P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.76(Δ/σ)max < 0.001
4709 reflectionsΔρmax = 0.39 e Å3
301 parametersΔρmin = 0.44 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin.

Statistics for all single and composite reflections —————————————————

Scan 2-theta R(int) Incid. factors Diffr. factors K Total I>2sig(I) 1 -119.0 0.0166 0.494 - 0.736 0.937 - 1.189 0.987 1442 1344 2 -119.0 0.0202 0.364 - 0.591 0.935 - 1.211 0.946 1637 1557 3 -119.0 0.0258 0.479 - 0.953 0.952 - 1.211 1.058 1234 1145 4 -119.0 0.0213 0.233 - 0.404 0.954 - 1.210 0.967 1531 1428 5 -119.0 0.0173 0.453 - 0.638 0.935 - 1.210 0.838 1646 1559 6 -119.0 0.0192 0.395 - 0.556 0.936 - 1.147 0.865 1679 1606 7 -119.0 0.0174 0.915 - 1.501 0.937 - 1.075 0.784 1618 1547 8 -119.0 0.0233 0.678 - 1.014 0.937 - 1.054 1.154 1269 1177 9 -70.0 0.0180 1.336 - 1.977 0.936 - 1.130 0.871 1755 1699 10 -70.0 0.0189 0.857 - 1.221 0.935 - 1.211 0.829 1760 1698 11 -70.0 0.0303 1.148 - 2.413 0.953 - 1.207 1.212 1511 1443 12 -70.0 0.0207 1.435 - 2.472 0.942 - 1.211 0.896 1820 1746 13 -70.0 0.0180 1.940 - 2.783 0.935 - 1.181 0.802 1837 1777 14 -70.0 0.0201 1.290 - 2.166 0.936 - 1.067 0.875 1727 1658 15 -35.0 0.0233 4.074 - 7.577 0.937 - 1.207 1.079 1014 987 16 -35.0 0.0207 4.757 - 7.034 0.935 - 1.210 1.005 1097 1065 17 -35.0 0.0302 4.825 - 8.043 0.936 - 1.054 1.196 973 929 18 -118.1 0.0224 0.212 - 0.402 0.936 - 1.209 0.821 1715 1558 19 -59.8 0.0277 1.473 - 1.994 0.953 - 1.129 1.144 304 281 20 -116.1 0.0256 0.232 - 0.593 0.937 - 1.087 0.906 1253 1140 21 -113.2 0.0221 1.047 - 1.272 0.952 - 1.120 0.879 816 764 22 -114.1 0.0269 0.208 - 0.238 0.946 - 1.127 0.929 325 309 23 -114.9 0.0289 0.400 - 0.449 0.972 - 1.035 1.128 205 187 24 -117.7 0.0201 0.218 - 0.243 0.958 - 1.124 0.866 291 268 25 -115.8 0.0215 0.271 - 0.602 0.937 - 1.210 0.812 1733 1586 26 -117.3 0.0274 0.402 - 0.519 0.952 - 1.208 0.953 1377 1246

All scans 0.0222 0.208 - 8.043 0.935 - 1.211 0.954 33569 31704

su = K * Sqrt[ sigma2(I) + (g<I>)2 ] where sigma(I) is estimated by SAINT

The above statistics are based on all non-rejected data, ignoring reflections without equivalents when estimating R(int) and K.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.61659 (12)0.39221 (11)0.05969 (8)0.0146 (2)
C40.86236 (12)0.67654 (11)0.01322 (8)0.0147 (2)
C110.55672 (13)0.19784 (11)0.04122 (9)0.0197 (2)
H11A0.56720.12540.01680.024*
H11B0.44810.22170.03200.024*
C120.60978 (13)0.15447 (11)0.13763 (9)0.0188 (2)
C130.71955 (13)0.05532 (12)0.14395 (10)0.0215 (3)
H130.75980.01530.08810.026*
C140.76892 (15)0.01612 (12)0.23306 (11)0.0266 (3)
H140.84140.05070.23650.032*
C150.71063 (15)0.07613 (13)0.31702 (10)0.0280 (3)
H150.74330.04950.37670.034*
C160.60296 (16)0.17648 (14)0.31150 (10)0.0291 (3)
H160.56470.21790.36800.035*
C170.55240 (14)0.21501 (12)0.22227 (10)0.0234 (3)
H170.47980.28170.21900.028*
C210.44409 (13)0.37663 (12)0.25297 (8)0.0192 (2)
H21A0.54690.39510.26200.023*
H21B0.39330.46160.23680.023*
C220.34803 (13)0.28278 (11)0.34891 (8)0.0171 (2)
C230.18674 (14)0.26791 (12)0.36483 (9)0.0205 (3)
H230.13690.31530.31550.025*
C240.09904 (14)0.18268 (13)0.45403 (10)0.0235 (3)
H240.00890.17390.46400.028*
C250.17187 (15)0.11060 (13)0.52820 (9)0.0239 (3)
H250.11320.05390.58780.029*
C260.33288 (15)0.12425 (13)0.51229 (9)0.0259 (3)
H260.38280.07600.56130.031*
C270.42005 (14)0.20971 (13)0.42336 (9)0.0230 (3)
H270.52800.21820.41350.028*
C410.99012 (12)0.75110 (11)0.07271 (8)0.0149 (2)
C421.05129 (14)0.86971 (11)0.06127 (9)0.0183 (2)
H421.01040.89650.00250.022*
C431.17093 (14)0.94877 (12)0.13473 (9)0.0216 (3)
H431.20911.02770.12580.026*
C441.23235 (14)0.90747 (12)0.22188 (9)0.0221 (3)
H441.31360.95860.27140.027*
C451.17411 (14)0.79116 (12)0.23601 (9)0.0208 (3)
H451.21530.76580.29540.025*
C461.05370 (12)0.71125 (11)0.16160 (8)0.0156 (2)
C1P0.7824 (2)0.50546 (17)0.44335 (11)0.0403 (4)
H1P10.67430.47580.46110.060*
H1P20.80230.55010.49180.060*
H1P30.84670.42880.44360.060*
C2P0.82029 (15)0.60256 (13)0.33882 (9)0.0234 (3)
H2P0.75330.67990.33920.028*
C3P0.98957 (17)0.65390 (17)0.30445 (13)0.0402 (4)
H3P11.05630.57870.30550.060*
H3P21.01160.70380.34920.060*
H3P31.00820.71180.23680.060*
N20.67780 (10)0.49282 (10)0.07869 (7)0.0158 (2)
N30.80167 (11)0.56226 (10)0.00335 (7)0.0148 (2)
H30.8374 (17)0.5377 (15)0.0493 (12)0.018*
O40.81506 (10)0.71966 (8)0.08894 (6)0.0207 (2)
O460.99837 (10)0.59585 (9)0.17513 (6)0.0180 (2)
H461.060 (2)0.5647 (18)0.2088 (13)0.027*
O3P0.78273 (10)0.53109 (8)0.27046 (6)0.0208 (2)
H3P0.779 (2)0.5940 (18)0.2162 (13)0.031*
S10.68242 (3)0.34452 (3)0.05435 (2)0.01616 (13)
S20.46135 (3)0.29405 (3)0.15092 (2)0.01668 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0163 (5)0.0142 (5)0.0125 (5)0.0008 (4)0.0019 (4)0.0034 (4)
C40.0165 (5)0.0135 (5)0.0148 (5)0.0022 (4)0.0045 (4)0.0041 (4)
C110.0217 (5)0.0179 (5)0.0201 (6)0.0049 (4)0.0011 (4)0.0089 (4)
C120.0185 (5)0.0177 (5)0.0207 (6)0.0044 (4)0.0006 (4)0.0090 (4)
C130.0225 (6)0.0170 (6)0.0251 (6)0.0025 (4)0.0031 (5)0.0073 (5)
C140.0260 (6)0.0201 (6)0.0329 (7)0.0017 (5)0.0021 (5)0.0132 (5)
C150.0326 (7)0.0289 (7)0.0235 (6)0.0082 (5)0.0032 (5)0.0168 (5)
C160.0330 (6)0.0347 (7)0.0224 (6)0.0033 (5)0.0083 (5)0.0108 (5)
C170.0241 (6)0.0235 (6)0.0245 (6)0.0001 (5)0.0057 (5)0.0096 (5)
C210.0250 (6)0.0183 (6)0.0139 (5)0.0036 (4)0.0017 (4)0.0055 (4)
C220.0231 (6)0.0161 (5)0.0126 (5)0.0005 (4)0.0021 (4)0.0062 (4)
C230.0224 (6)0.0204 (6)0.0200 (6)0.0012 (4)0.0050 (5)0.0075 (5)
C240.0208 (5)0.0243 (6)0.0249 (6)0.0025 (4)0.0008 (5)0.0095 (5)
C250.0302 (6)0.0228 (6)0.0152 (5)0.0046 (5)0.0033 (5)0.0059 (4)
C260.0318 (6)0.0290 (7)0.0150 (5)0.0012 (5)0.0055 (5)0.0025 (5)
C270.0211 (5)0.0296 (6)0.0171 (6)0.0005 (5)0.0031 (4)0.0051 (5)
C410.0159 (5)0.0143 (5)0.0142 (5)0.0028 (4)0.0032 (4)0.0036 (4)
C420.0223 (5)0.0144 (5)0.0181 (5)0.0019 (4)0.0036 (4)0.0053 (4)
C430.0256 (6)0.0143 (5)0.0230 (6)0.0027 (4)0.0050 (5)0.0021 (4)
C440.0229 (5)0.0204 (6)0.0179 (5)0.0024 (4)0.0013 (4)0.0009 (4)
C450.0225 (5)0.0234 (6)0.0145 (5)0.0021 (4)0.0017 (4)0.0037 (4)
C460.0166 (5)0.0156 (5)0.0152 (5)0.0029 (4)0.0046 (4)0.0045 (4)
C1P0.0569 (9)0.0450 (9)0.0208 (7)0.0048 (7)0.0077 (6)0.0126 (6)
C2P0.0266 (6)0.0253 (6)0.0220 (6)0.0013 (5)0.0034 (5)0.0149 (5)
C3P0.0331 (7)0.0464 (9)0.0482 (9)0.0101 (6)0.0032 (6)0.0297 (8)
N20.0165 (4)0.0175 (5)0.0126 (4)0.0007 (4)0.0016 (4)0.0036 (4)
N30.0168 (4)0.0164 (5)0.0109 (4)0.0007 (3)0.0002 (3)0.0058 (4)
O40.0247 (4)0.0181 (4)0.0186 (4)0.0021 (3)0.0019 (3)0.0097 (3)
O460.0193 (4)0.0200 (4)0.0160 (4)0.0000 (3)0.0009 (3)0.0098 (3)
O3P0.0246 (4)0.0219 (4)0.0181 (4)0.0007 (3)0.0041 (3)0.0097 (3)
S10.0189 (2)0.01553 (19)0.01400 (19)0.00217 (12)0.00015 (13)0.00674 (13)
S20.0191 (2)0.0174 (2)0.01252 (19)0.00410 (12)0.00066 (12)0.00447 (14)
Geometric parameters (Å, º) top
C1—N21.2860 (15)C22—C231.3892 (16)
C1—S21.7592 (13)C23—C241.3928 (18)
C1—S11.7637 (12)C24—C251.3897 (18)
C4—O41.2386 (15)C25—C261.3858 (18)
C4—N31.3483 (16)C26—C271.3898 (18)
C4—C411.4941 (16)C41—C421.3995 (17)
C11—C121.5048 (16)C41—C461.4053 (16)
C11—S11.8274 (13)C42—C431.3879 (18)
C12—C171.3906 (17)C43—C441.3882 (18)
C12—C131.3953 (17)C44—C451.3838 (18)
C13—C141.3864 (19)C45—C461.4011 (17)
C14—C151.386 (2)C46—O461.3611 (15)
C15—C161.391 (2)C1P—C2P1.5118 (19)
C16—C171.3855 (19)C2P—O3P1.4446 (15)
C21—C221.5127 (16)C2P—C3P1.5142 (19)
C21—S21.8222 (13)N2—N31.3858 (14)
C22—C271.3914 (16)
N2—C1—S2119.61 (9)C24—C25—C26119.22 (11)
N2—C1—S1123.13 (9)C25—C26—C27120.24 (11)
S2—C1—S1117.26 (7)C26—C27—C22120.92 (11)
O4—C4—N3122.43 (10)C42—C41—C46118.33 (11)
O4—C4—C41120.81 (11)C42—C41—C4115.95 (10)
N3—C4—C41116.76 (10)C46—C41—C4125.71 (11)
C12—C11—S1106.26 (8)C43—C42—C41122.23 (11)
C17—C12—C13119.20 (11)C42—C43—C44118.53 (12)
C17—C12—C11120.28 (11)C45—C44—C43120.80 (11)
C13—C12—C11120.50 (11)C44—C45—C46120.57 (11)
C14—C13—C12120.38 (12)O46—C46—C45120.38 (11)
C15—C14—C13120.20 (12)O46—C46—C41120.10 (10)
C14—C15—C16119.59 (12)C45—C46—C41119.52 (11)
C17—C16—C15120.32 (12)O3P—C2P—C1P106.73 (11)
C16—C17—C12120.30 (11)O3P—C2P—C3P110.53 (11)
C22—C21—S2107.91 (8)C1P—C2P—C3P112.98 (13)
C27—C22—C23118.63 (11)C1—N2—N3115.49 (10)
C27—C22—C21120.38 (11)C4—N3—N2119.04 (10)
C23—C22—C21120.98 (10)C1—S1—C11104.87 (6)
C22—C23—C24120.57 (11)C1—S2—C21100.55 (6)
C25—C24—C23120.41 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3P—H3P···O40.867 (17)1.874 (17)2.7285 (16)167.8 (16)
O46—H46···O3Pi0.759 (18)1.862 (18)2.6131 (14)170.1 (17)
N3—H3···S10.835 (16)2.449 (15)2.8554 (13)110.9 (12)
N3—H3···O460.835 (16)1.953 (15)2.6416 (16)139.1 (14)
C21—H21B···S1ii0.973.013.7899 (17)139
C21—H21A···O3P0.972.563.4847 (17)159
C11—H11B···O4ii0.972.633.5313 (17)155
Symmetry codes: (i) x+2, y+1, z; (ii) x+1, y+1, z.
 

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