The asymmetric unit of the title compound, C
22H
18N
4O
2S
2, contains two molecules. In one of them, the dihedral angles between the central benzene ring and the phenyl rings are 16.97 (8) and 20.97 (8)°, while the phenyl rings make a dihedral angle of 37.87 (8)°. In the other molecule, the corresponding values are 34.92 (7), 53.90 (7) and 60.68 (8)°, respectively. In each molecule, two intramolecular N—H

O hydrogen bonds generate
S(6) rings and a short C—H

S contact also occurs. In the crystal, N—H

S, N—H

O, C—H

O and C—H

S interactions link the molecules into a three-dimensional network.
Supporting information
CCDC reference: 963454
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.044
- wR factor = 0.122
- Data-to-parameter ratio = 25.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 2.729
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 30
Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF ? Do !
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal .......... 0.00100 Deg.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 18
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 153
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
4 ALERT level G = General information/check it is not something unexpected
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
Isophthaloyl dichloride (1 mmol) in 15 ml of dry acetone was added drop wise to
a suspension of potassium thiocyanate (2 mmol) in 15 ml of dry acetone. The
mixture was stirred for 1 h at room temperature and the white potassium
chloride (KCl) was filtered. Aniline (2 mmol) in dry acetone (15 ml) was added
into the filtrate and heated under reflux for 7 h. The mixture was cooled to
room temperature and filtered. The filtrate was poured into ice in a beaker to
form solid. The crude was filtered, washed with ethanol and recrystallized
from ethanol-acetonitrile (1:1) solution to yield colourless blocks.
N bound H atoms were located from difference Fourier maps and freely refined.
The remaining H atoms were positioned geometrically and refined using a riding
model with with C–H = 0.95 Å and Uiso(H) = 1.2Ueq(C).
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
N,
N'-Bis(phenylcarbamothioyl)benzene-1,3-dicarboxamide
top
Crystal data top
C22H18N4O2S2 | Z = 4 |
Mr = 434.52 | F(000) = 904 |
Triclinic, P1 | Dx = 1.438 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.1812 (2) Å | Cell parameters from 9969 reflections |
b = 11.5623 (2) Å | θ = 2.6–32.6° |
c = 16.4471 (2) Å | µ = 0.29 mm−1 |
α = 101.420 (1)° | T = 100 K |
β = 98.127 (1)° | Block, colourless |
γ = 101.316 (1)° | 0.47 × 0.33 × 0.11 mm |
V = 2007.43 (6) Å3 | |
Data collection top
Bruker APEX DUO CCD diffractometer | 14580 independent reflections |
Radiation source: fine-focus sealed tube | 11642 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
ϕ and ω scans | θmax = 32.7°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −16→16 |
Tmin = 0.876, Tmax = 0.968 | k = −17→17 |
41276 measured reflections | l = −24→24 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.060P)2 + 0.666P] where P = (Fo2 + 2Fc2)/3 |
14580 reflections | (Δ/σ)max = 0.002 |
573 parameters | Δρmax = 0.53 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Crystal data top
C22H18N4O2S2 | γ = 101.316 (1)° |
Mr = 434.52 | V = 2007.43 (6) Å3 |
Triclinic, P1 | Z = 4 |
a = 11.1812 (2) Å | Mo Kα radiation |
b = 11.5623 (2) Å | µ = 0.29 mm−1 |
c = 16.4471 (2) Å | T = 100 K |
α = 101.420 (1)° | 0.47 × 0.33 × 0.11 mm |
β = 98.127 (1)° | |
Data collection top
Bruker APEX DUO CCD diffractometer | 14580 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 11642 reflections with I > 2σ(I) |
Tmin = 0.876, Tmax = 0.968 | Rint = 0.034 |
41276 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.53 e Å−3 |
14580 reflections | Δρmin = −0.28 e Å−3 |
573 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1A | 0.56880 (4) | 0.73303 (3) | −0.12090 (2) | 0.01838 (7) | |
S2A | 0.87429 (3) | 0.08533 (3) | 0.22615 (2) | 0.01788 (7) | |
O1A | 0.70303 (10) | 0.43088 (9) | −0.02345 (6) | 0.01691 (19) | |
O2A | 0.84638 (12) | 0.45365 (10) | 0.37157 (6) | 0.0243 (2) | |
N1A | 0.58550 (12) | 0.49816 (11) | −0.15304 (7) | 0.0158 (2) | |
N2A | 0.63967 (11) | 0.60868 (10) | −0.01410 (7) | 0.0149 (2) | |
N3A | 0.85008 (11) | 0.31200 (10) | 0.25405 (7) | 0.0151 (2) | |
N4A | 0.86694 (12) | 0.23330 (11) | 0.37280 (7) | 0.0174 (2) | |
C1A | 0.55898 (15) | 0.34542 (13) | −0.27844 (9) | 0.0203 (3) | |
H1AA | 0.5931 | 0.2985 | −0.2440 | 0.024* | |
C2A | 0.52227 (17) | 0.29874 (14) | −0.36505 (9) | 0.0255 (3) | |
H2AA | 0.5314 | 0.2201 | −0.3895 | 0.031* | |
C3A | 0.47246 (16) | 0.36650 (15) | −0.41579 (9) | 0.0237 (3) | |
H3AA | 0.4475 | 0.3348 | −0.4750 | 0.028* | |
C4A | 0.45953 (17) | 0.48052 (15) | −0.37945 (9) | 0.0273 (3) | |
H4AA | 0.4254 | 0.5271 | −0.4142 | 0.033* | |
C5A | 0.49557 (16) | 0.52866 (15) | −0.29272 (9) | 0.0257 (3) | |
H5AA | 0.4858 | 0.6072 | −0.2685 | 0.031* | |
C6A | 0.54596 (13) | 0.46072 (12) | −0.24196 (8) | 0.0148 (2) | |
C7A | 0.59717 (12) | 0.60539 (12) | −0.09913 (8) | 0.0139 (2) | |
C8A | 0.69641 (12) | 0.52843 (12) | 0.01927 (8) | 0.0137 (2) | |
C9A | 0.74873 (12) | 0.56819 (12) | 0.11167 (8) | 0.0140 (2) | |
C10A | 0.77808 (14) | 0.68980 (12) | 0.15500 (8) | 0.0178 (2) | |
H10A | 0.7681 | 0.7507 | 0.1251 | 0.021* | |
C11A | 0.82180 (15) | 0.72217 (13) | 0.24174 (9) | 0.0212 (3) | |
H11A | 0.8402 | 0.8048 | 0.2713 | 0.025* | |
C12A | 0.83832 (14) | 0.63308 (13) | 0.28471 (8) | 0.0197 (3) | |
H12A | 0.8658 | 0.6548 | 0.3442 | 0.024* | |
C13A | 0.81496 (13) | 0.51154 (12) | 0.24138 (8) | 0.0148 (2) | |
C14A | 0.76909 (12) | 0.47850 (12) | 0.15455 (8) | 0.0139 (2) | |
H14A | 0.7519 | 0.3960 | 0.1248 | 0.017* | |
C15A | 0.83784 (13) | 0.42367 (12) | 0.29426 (8) | 0.0162 (2) | |
C16A | 0.86424 (12) | 0.21278 (12) | 0.28948 (8) | 0.0143 (2) | |
C17A | 0.86565 (13) | 0.15044 (13) | 0.42592 (8) | 0.0167 (2) | |
C18A | 0.92475 (14) | 0.19911 (14) | 0.50987 (8) | 0.0196 (3) | |
H18A | 0.9674 | 0.2820 | 0.5275 | 0.024* | |
C19A | 0.92110 (15) | 0.12619 (14) | 0.56758 (9) | 0.0218 (3) | |
H19A | 0.9603 | 0.1597 | 0.6249 | 0.026* | |
C20A | 0.86063 (15) | 0.00499 (14) | 0.54201 (9) | 0.0225 (3) | |
H20A | 0.8603 | −0.0454 | 0.5812 | 0.027* | |
C21A | 0.80024 (15) | −0.04280 (14) | 0.45842 (10) | 0.0228 (3) | |
H21A | 0.7577 | −0.1258 | 0.4411 | 0.027* | |
C22A | 0.80140 (14) | 0.02947 (13) | 0.40006 (9) | 0.0198 (3) | |
H22A | 0.7589 | −0.0033 | 0.3434 | 0.024* | |
S1B | 0.04057 (4) | 0.37065 (3) | 0.07939 (2) | 0.01870 (8) | |
S2B | 0.48059 (4) | 1.19306 (3) | −0.11559 (2) | 0.01956 (8) | |
O1B | 0.13462 (11) | 0.75257 (9) | 0.24757 (6) | 0.0201 (2) | |
O2B | 0.30600 (9) | 0.81658 (9) | −0.08677 (6) | 0.01593 (18) | |
N1B | 0.13188 (11) | 0.52187 (11) | 0.23333 (7) | 0.0154 (2) | |
N2B | 0.08889 (11) | 0.60964 (10) | 0.12230 (7) | 0.0145 (2) | |
N3B | 0.36721 (11) | 1.02400 (10) | −0.04957 (7) | 0.0131 (2) | |
N4B | 0.45042 (11) | 0.95054 (10) | −0.16480 (7) | 0.0139 (2) | |
C1B | 0.18586 (14) | 0.33048 (13) | 0.25490 (9) | 0.0195 (3) | |
H1BA | 0.1860 | 0.3028 | 0.1966 | 0.023* | |
C2B | 0.21509 (16) | 0.26110 (14) | 0.31178 (10) | 0.0255 (3) | |
H2BA | 0.2354 | 0.1857 | 0.2920 | 0.031* | |
C3B | 0.21489 (16) | 0.30126 (15) | 0.39736 (10) | 0.0269 (3) | |
H3BA | 0.2337 | 0.2528 | 0.4356 | 0.032* | |
C4B | 0.18724 (16) | 0.41160 (16) | 0.42659 (9) | 0.0266 (3) | |
H4BA | 0.1882 | 0.4396 | 0.4851 | 0.032* | |
C5B | 0.15812 (15) | 0.48148 (14) | 0.37044 (9) | 0.0220 (3) | |
H5BA | 0.1392 | 0.5574 | 0.3905 | 0.026* | |
C6B | 0.15657 (13) | 0.44021 (12) | 0.28430 (8) | 0.0155 (2) | |
C7B | 0.09048 (12) | 0.50324 (12) | 0.15029 (8) | 0.0139 (2) | |
C8B | 0.11636 (12) | 0.72663 (12) | 0.16982 (8) | 0.0140 (2) | |
C9B | 0.12775 (12) | 0.82365 (11) | 0.12203 (8) | 0.0133 (2) | |
C10B | 0.08163 (13) | 0.92559 (12) | 0.14973 (8) | 0.0168 (2) | |
H10B | 0.0379 | 0.9289 | 0.1953 | 0.020* | |
C11B | 0.09979 (13) | 1.02205 (12) | 0.11061 (9) | 0.0173 (2) | |
H11B | 0.0644 | 1.0893 | 0.1272 | 0.021* | |
C12B | 0.16985 (13) | 1.01978 (12) | 0.04711 (8) | 0.0151 (2) | |
H12B | 0.1838 | 1.0863 | 0.0210 | 0.018* | |
C13B | 0.21967 (12) | 0.92008 (11) | 0.02166 (8) | 0.0126 (2) | |
C14B | 0.19528 (12) | 0.81962 (11) | 0.05684 (8) | 0.0126 (2) | |
H14B | 0.2243 | 0.7494 | 0.0367 | 0.015* | |
C15B | 0.29979 (12) | 0.91422 (11) | −0.04329 (7) | 0.0127 (2) | |
C16B | 0.43319 (12) | 1.04832 (11) | −0.11312 (7) | 0.0126 (2) | |
C17B | 0.49238 (12) | 0.94255 (12) | −0.24293 (8) | 0.0135 (2) | |
C18B | 0.58498 (13) | 1.02975 (12) | −0.25842 (8) | 0.0168 (2) | |
H18B | 0.6257 | 1.0996 | −0.2152 | 0.020* | |
C19B | 0.61801 (14) | 1.01436 (14) | −0.33785 (9) | 0.0204 (3) | |
H19B | 0.6821 | 1.0737 | −0.3483 | 0.025* | |
C20B | 0.55823 (14) | 0.91338 (14) | −0.40168 (9) | 0.0213 (3) | |
H20B | 0.5787 | 0.9051 | −0.4563 | 0.026* | |
C21B | 0.46833 (14) | 0.82451 (14) | −0.38515 (9) | 0.0211 (3) | |
H21B | 0.4283 | 0.7543 | −0.4283 | 0.025* | |
C22B | 0.43662 (13) | 0.83782 (13) | −0.30554 (8) | 0.0171 (2) | |
H22B | 0.3770 | 0.7755 | −0.2939 | 0.020* | |
H1NA | 0.6098 (18) | 0.4465 (18) | −0.1306 (12) | 0.022 (5)* | |
H2NA | 0.6244 (18) | 0.6662 (18) | 0.0208 (12) | 0.026 (5)* | |
H3NA | 0.8458 (18) | 0.2974 (17) | 0.2000 (12) | 0.023 (5)* | |
H4NA | 0.869 (2) | 0.310 (2) | 0.3996 (13) | 0.035 (6)* | |
H1NB | 0.1426 (19) | 0.5963 (19) | 0.2599 (13) | 0.030 (5)* | |
H2NB | 0.0724 (19) | 0.6022 (18) | 0.0702 (12) | 0.028 (5)* | |
H3NB | 0.3662 (18) | 1.0839 (19) | −0.0115 (12) | 0.027 (5)* | |
H4NB | 0.4132 (19) | 0.8814 (19) | −0.1562 (12) | 0.027 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1A | 0.02852 (18) | 0.01355 (14) | 0.01349 (14) | 0.00880 (13) | 0.00118 (12) | 0.00214 (11) |
S2A | 0.02273 (17) | 0.01587 (15) | 0.01761 (15) | 0.00915 (13) | 0.00616 (12) | 0.00355 (12) |
O1A | 0.0239 (5) | 0.0119 (4) | 0.0144 (4) | 0.0059 (4) | 0.0023 (4) | 0.0013 (3) |
O2A | 0.0430 (7) | 0.0183 (5) | 0.0123 (4) | 0.0121 (5) | 0.0031 (4) | 0.0018 (4) |
N1A | 0.0224 (6) | 0.0125 (5) | 0.0121 (5) | 0.0067 (4) | 0.0007 (4) | 0.0013 (4) |
N2A | 0.0215 (6) | 0.0129 (5) | 0.0111 (4) | 0.0078 (4) | 0.0027 (4) | 0.0009 (4) |
N3A | 0.0207 (6) | 0.0138 (5) | 0.0113 (4) | 0.0054 (4) | 0.0027 (4) | 0.0027 (4) |
N4A | 0.0251 (6) | 0.0147 (5) | 0.0128 (5) | 0.0068 (5) | 0.0013 (4) | 0.0035 (4) |
C1A | 0.0290 (8) | 0.0156 (6) | 0.0156 (6) | 0.0056 (5) | 0.0030 (5) | 0.0024 (5) |
C2A | 0.0392 (9) | 0.0191 (7) | 0.0163 (6) | 0.0097 (6) | 0.0028 (6) | −0.0017 (5) |
C3A | 0.0311 (8) | 0.0244 (7) | 0.0130 (5) | 0.0068 (6) | 0.0019 (5) | −0.0002 (5) |
C4A | 0.0396 (9) | 0.0255 (8) | 0.0157 (6) | 0.0124 (7) | −0.0034 (6) | 0.0031 (5) |
C5A | 0.0376 (9) | 0.0212 (7) | 0.0157 (6) | 0.0137 (6) | −0.0047 (6) | −0.0015 (5) |
C6A | 0.0167 (6) | 0.0145 (6) | 0.0115 (5) | 0.0027 (5) | 0.0016 (4) | 0.0008 (4) |
C7A | 0.0159 (6) | 0.0130 (5) | 0.0121 (5) | 0.0036 (5) | 0.0018 (4) | 0.0016 (4) |
C8A | 0.0157 (6) | 0.0125 (5) | 0.0131 (5) | 0.0035 (4) | 0.0031 (4) | 0.0032 (4) |
C9A | 0.0168 (6) | 0.0123 (5) | 0.0129 (5) | 0.0045 (5) | 0.0022 (4) | 0.0020 (4) |
C10A | 0.0234 (7) | 0.0123 (5) | 0.0167 (6) | 0.0054 (5) | −0.0001 (5) | 0.0026 (5) |
C11A | 0.0303 (8) | 0.0128 (6) | 0.0170 (6) | 0.0054 (5) | −0.0020 (5) | −0.0005 (5) |
C12A | 0.0274 (7) | 0.0150 (6) | 0.0139 (5) | 0.0053 (5) | −0.0011 (5) | 0.0005 (5) |
C13A | 0.0178 (6) | 0.0132 (5) | 0.0133 (5) | 0.0043 (5) | 0.0021 (4) | 0.0027 (4) |
C14A | 0.0168 (6) | 0.0114 (5) | 0.0129 (5) | 0.0036 (4) | 0.0023 (4) | 0.0014 (4) |
C15A | 0.0201 (6) | 0.0145 (6) | 0.0133 (5) | 0.0043 (5) | 0.0015 (5) | 0.0026 (4) |
C16A | 0.0136 (6) | 0.0150 (6) | 0.0148 (5) | 0.0038 (5) | 0.0023 (4) | 0.0045 (4) |
C17A | 0.0195 (6) | 0.0177 (6) | 0.0148 (5) | 0.0073 (5) | 0.0040 (5) | 0.0047 (5) |
C18A | 0.0242 (7) | 0.0197 (6) | 0.0155 (6) | 0.0058 (5) | 0.0035 (5) | 0.0048 (5) |
C19A | 0.0274 (7) | 0.0255 (7) | 0.0147 (6) | 0.0075 (6) | 0.0060 (5) | 0.0068 (5) |
C20A | 0.0264 (7) | 0.0256 (7) | 0.0215 (6) | 0.0083 (6) | 0.0114 (5) | 0.0126 (6) |
C21A | 0.0267 (8) | 0.0204 (7) | 0.0245 (7) | 0.0057 (6) | 0.0096 (6) | 0.0090 (5) |
C22A | 0.0227 (7) | 0.0190 (6) | 0.0173 (6) | 0.0043 (5) | 0.0035 (5) | 0.0041 (5) |
S1B | 0.02706 (18) | 0.01150 (14) | 0.01460 (14) | 0.00189 (13) | −0.00134 (12) | 0.00244 (11) |
S2B | 0.02636 (18) | 0.01142 (14) | 0.02378 (16) | 0.00391 (13) | 0.01465 (14) | 0.00421 (12) |
O1B | 0.0331 (6) | 0.0156 (5) | 0.0122 (4) | 0.0055 (4) | 0.0074 (4) | 0.0026 (3) |
O2B | 0.0225 (5) | 0.0117 (4) | 0.0144 (4) | 0.0048 (4) | 0.0068 (4) | 0.0020 (3) |
N1B | 0.0206 (6) | 0.0126 (5) | 0.0127 (5) | 0.0034 (4) | 0.0017 (4) | 0.0034 (4) |
N2B | 0.0202 (6) | 0.0131 (5) | 0.0106 (4) | 0.0036 (4) | 0.0032 (4) | 0.0036 (4) |
N3B | 0.0173 (5) | 0.0104 (5) | 0.0115 (4) | 0.0022 (4) | 0.0061 (4) | 0.0009 (4) |
N4B | 0.0174 (5) | 0.0123 (5) | 0.0129 (4) | 0.0040 (4) | 0.0060 (4) | 0.0023 (4) |
C1B | 0.0236 (7) | 0.0176 (6) | 0.0178 (6) | 0.0058 (5) | 0.0015 (5) | 0.0055 (5) |
C2B | 0.0328 (8) | 0.0182 (7) | 0.0249 (7) | 0.0066 (6) | −0.0020 (6) | 0.0082 (6) |
C3B | 0.0314 (8) | 0.0237 (7) | 0.0231 (7) | 0.0004 (6) | −0.0043 (6) | 0.0127 (6) |
C4B | 0.0336 (9) | 0.0292 (8) | 0.0152 (6) | 0.0026 (7) | 0.0008 (6) | 0.0085 (6) |
C5B | 0.0296 (8) | 0.0216 (7) | 0.0147 (6) | 0.0066 (6) | 0.0024 (5) | 0.0043 (5) |
C6B | 0.0162 (6) | 0.0163 (6) | 0.0139 (5) | 0.0027 (5) | 0.0008 (4) | 0.0059 (4) |
C7B | 0.0158 (6) | 0.0131 (5) | 0.0138 (5) | 0.0034 (5) | 0.0035 (4) | 0.0043 (4) |
C8B | 0.0160 (6) | 0.0128 (5) | 0.0140 (5) | 0.0033 (5) | 0.0052 (4) | 0.0031 (4) |
C9B | 0.0158 (6) | 0.0111 (5) | 0.0131 (5) | 0.0026 (4) | 0.0044 (4) | 0.0027 (4) |
C10B | 0.0203 (6) | 0.0150 (6) | 0.0171 (6) | 0.0055 (5) | 0.0089 (5) | 0.0035 (5) |
C11B | 0.0200 (6) | 0.0127 (5) | 0.0218 (6) | 0.0065 (5) | 0.0092 (5) | 0.0039 (5) |
C12B | 0.0179 (6) | 0.0123 (5) | 0.0164 (5) | 0.0039 (5) | 0.0051 (5) | 0.0042 (4) |
C13B | 0.0154 (6) | 0.0104 (5) | 0.0114 (5) | 0.0021 (4) | 0.0033 (4) | 0.0016 (4) |
C14B | 0.0155 (6) | 0.0104 (5) | 0.0119 (5) | 0.0035 (4) | 0.0033 (4) | 0.0014 (4) |
C15B | 0.0161 (6) | 0.0121 (5) | 0.0102 (5) | 0.0036 (4) | 0.0027 (4) | 0.0027 (4) |
C16B | 0.0137 (5) | 0.0132 (5) | 0.0114 (5) | 0.0038 (4) | 0.0032 (4) | 0.0030 (4) |
C17B | 0.0153 (6) | 0.0141 (5) | 0.0123 (5) | 0.0057 (5) | 0.0039 (4) | 0.0027 (4) |
C18B | 0.0178 (6) | 0.0150 (6) | 0.0170 (6) | 0.0020 (5) | 0.0064 (5) | 0.0015 (5) |
C19B | 0.0249 (7) | 0.0200 (6) | 0.0195 (6) | 0.0061 (5) | 0.0117 (5) | 0.0055 (5) |
C20B | 0.0252 (7) | 0.0244 (7) | 0.0159 (6) | 0.0069 (6) | 0.0096 (5) | 0.0036 (5) |
C21B | 0.0229 (7) | 0.0222 (7) | 0.0155 (6) | 0.0047 (6) | 0.0055 (5) | −0.0026 (5) |
C22B | 0.0173 (6) | 0.0150 (6) | 0.0179 (6) | 0.0029 (5) | 0.0062 (5) | 0.0003 (5) |
Geometric parameters (Å, º) top
S1A—C7A | 1.6636 (14) | S1B—C7B | 1.6715 (13) |
S2A—C16A | 1.6611 (14) | S2B—C16B | 1.6638 (13) |
O1A—C8A | 1.2267 (15) | O1B—C8B | 1.2317 (15) |
O2A—C15A | 1.2346 (15) | O2B—C15B | 1.2312 (15) |
N1A—C7A | 1.3449 (16) | N1B—C7B | 1.3385 (16) |
N1A—C6A | 1.4188 (16) | N1B—C6B | 1.4215 (17) |
N1A—H1NA | 0.83 (2) | N1B—H1NB | 0.86 (2) |
N2A—C8A | 1.3780 (17) | N2B—C8B | 1.3731 (17) |
N2A—C7A | 1.4026 (16) | N2B—C7B | 1.3986 (17) |
N2A—H2NA | 0.85 (2) | N2B—H2NB | 0.83 (2) |
N3A—C15A | 1.3711 (17) | N3B—C15B | 1.3741 (16) |
N3A—C16A | 1.4110 (17) | N3B—C16B | 1.4032 (15) |
N3A—H3NA | 0.864 (19) | N3B—H3NB | 0.84 (2) |
N4A—C16A | 1.3385 (16) | N4B—C16B | 1.3375 (16) |
N4A—C17A | 1.4182 (17) | N4B—C17B | 1.4215 (16) |
N4A—H4NA | 0.90 (2) | N4B—H4NB | 0.87 (2) |
C1A—C2A | 1.3900 (19) | C1B—C6B | 1.384 (2) |
C1A—C6A | 1.3938 (19) | C1B—C2B | 1.393 (2) |
C1A—H1AA | 0.9500 | C1B—H1BA | 0.9500 |
C2A—C3A | 1.385 (2) | C2B—C3B | 1.392 (2) |
C2A—H2AA | 0.9500 | C2B—H2BA | 0.9500 |
C3A—C4A | 1.380 (2) | C3B—C4B | 1.381 (2) |
C3A—H3AA | 0.9500 | C3B—H3BA | 0.9500 |
C4A—C5A | 1.394 (2) | C4B—C5B | 1.388 (2) |
C4A—H4AA | 0.9500 | C4B—H4BA | 0.9500 |
C5A—C6A | 1.390 (2) | C5B—C6B | 1.3990 (18) |
C5A—H5AA | 0.9500 | C5B—H5BA | 0.9500 |
C8A—C9A | 1.4932 (17) | C8B—C9B | 1.4879 (18) |
C9A—C10A | 1.3960 (18) | C9B—C14B | 1.3946 (17) |
C9A—C14A | 1.4005 (18) | C9B—C10B | 1.3982 (18) |
C10A—C11A | 1.3907 (19) | C10B—C11B | 1.3898 (19) |
C10A—H10A | 0.9500 | C10B—H10B | 0.9500 |
C11A—C12A | 1.386 (2) | C11B—C12B | 1.3906 (18) |
C11A—H11A | 0.9500 | C11B—H11B | 0.9500 |
C12A—C13A | 1.3992 (19) | C12B—C13B | 1.3933 (18) |
C12A—H12A | 0.9500 | C12B—H12B | 0.9500 |
C13A—C14A | 1.3958 (17) | C13B—C14B | 1.3946 (17) |
C13A—C15A | 1.4977 (18) | C13B—C15B | 1.4880 (17) |
C14A—H14A | 0.9500 | C14B—H14B | 0.9500 |
C17A—C22A | 1.392 (2) | C17B—C18B | 1.3856 (18) |
C17A—C18A | 1.3958 (19) | C17B—C22B | 1.3942 (18) |
C18A—C19A | 1.388 (2) | C18B—C19B | 1.3947 (18) |
C18A—H18A | 0.9500 | C18B—H18B | 0.9500 |
C19A—C20A | 1.383 (2) | C19B—C20B | 1.386 (2) |
C19A—H19A | 0.9500 | C19B—H19B | 0.9500 |
C20A—C21A | 1.393 (2) | C20B—C21B | 1.387 (2) |
C20A—H20A | 0.9500 | C20B—H20B | 0.9500 |
C21A—C22A | 1.392 (2) | C21B—C22B | 1.3916 (18) |
C21A—H21A | 0.9500 | C21B—H21B | 0.9500 |
C22A—H22A | 0.9500 | C22B—H22B | 0.9500 |
| | | |
C7A—N1A—C6A | 131.12 (12) | C7B—N1B—C6B | 131.26 (12) |
C7A—N1A—H1NA | 114.1 (13) | C7B—N1B—H1NB | 113.1 (14) |
C6A—N1A—H1NA | 114.7 (13) | C6B—N1B—H1NB | 115.6 (13) |
C8A—N2A—C7A | 128.61 (11) | C8B—N2B—C7B | 128.08 (11) |
C8A—N2A—H2NA | 116.9 (13) | C8B—N2B—H2NB | 115.2 (14) |
C7A—N2A—H2NA | 114.4 (13) | C7B—N2B—H2NB | 116.6 (14) |
C15A—N3A—C16A | 127.99 (11) | C15B—N3B—C16B | 127.96 (11) |
C15A—N3A—H3NA | 118.0 (13) | C15B—N3B—H3NB | 115.5 (14) |
C16A—N3A—H3NA | 114.0 (13) | C16B—N3B—H3NB | 116.5 (14) |
C16A—N4A—C17A | 128.96 (12) | C16B—N4B—C17B | 128.47 (11) |
C16A—N4A—H4NA | 116.6 (13) | C16B—N4B—H4NB | 114.5 (13) |
C17A—N4A—H4NA | 114.4 (13) | C17B—N4B—H4NB | 114.9 (13) |
C2A—C1A—C6A | 120.28 (14) | C6B—C1B—C2B | 119.28 (13) |
C2A—C1A—H1AA | 119.9 | C6B—C1B—H1BA | 120.4 |
C6A—C1A—H1AA | 119.9 | C2B—C1B—H1BA | 120.4 |
C3A—C2A—C1A | 120.24 (14) | C3B—C2B—C1B | 120.57 (15) |
C3A—C2A—H2AA | 119.9 | C3B—C2B—H2BA | 119.7 |
C1A—C2A—H2AA | 119.9 | C1B—C2B—H2BA | 119.7 |
C4A—C3A—C2A | 119.32 (13) | C4B—C3B—C2B | 119.95 (14) |
C4A—C3A—H3AA | 120.3 | C4B—C3B—H3BA | 120.0 |
C2A—C3A—H3AA | 120.3 | C2B—C3B—H3BA | 120.0 |
C3A—C4A—C5A | 121.22 (15) | C3B—C4B—C5B | 119.92 (14) |
C3A—C4A—H4AA | 119.4 | C3B—C4B—H4BA | 120.0 |
C5A—C4A—H4AA | 119.4 | C5B—C4B—H4BA | 120.0 |
C6A—C5A—C4A | 119.37 (14) | C4B—C5B—C6B | 120.07 (14) |
C6A—C5A—H5AA | 120.3 | C4B—C5B—H5BA | 120.0 |
C4A—C5A—H5AA | 120.3 | C6B—C5B—H5BA | 120.0 |
C5A—C6A—C1A | 119.56 (12) | C1B—C6B—C5B | 120.19 (12) |
C5A—C6A—N1A | 125.23 (12) | C1B—C6B—N1B | 124.44 (12) |
C1A—C6A—N1A | 115.21 (12) | C5B—C6B—N1B | 115.22 (12) |
N1A—C7A—N2A | 115.00 (11) | N1B—C7B—N2B | 114.03 (11) |
N1A—C7A—S1A | 128.26 (10) | N1B—C7B—S1B | 127.76 (10) |
N2A—C7A—S1A | 116.74 (9) | N2B—C7B—S1B | 118.21 (9) |
O1A—C8A—N2A | 122.67 (12) | O1B—C8B—N2B | 123.30 (12) |
O1A—C8A—C9A | 122.15 (12) | O1B—C8B—C9B | 120.59 (12) |
N2A—C8A—C9A | 115.18 (11) | N2B—C8B—C9B | 116.07 (11) |
C10A—C9A—C14A | 120.18 (12) | C14B—C9B—C10B | 120.33 (12) |
C10A—C9A—C8A | 122.27 (11) | C14B—C9B—C8B | 120.58 (11) |
C14A—C9A—C8A | 117.55 (11) | C10B—C9B—C8B | 118.70 (11) |
C11A—C10A—C9A | 120.28 (12) | C11B—C10B—C9B | 120.02 (12) |
C11A—C10A—H10A | 119.9 | C11B—C10B—H10B | 120.0 |
C9A—C10A—H10A | 119.9 | C9B—C10B—H10B | 120.0 |
C12A—C11A—C10A | 119.56 (13) | C10B—C11B—C12B | 119.78 (12) |
C12A—C11A—H11A | 120.2 | C10B—C11B—H11B | 120.1 |
C10A—C11A—H11A | 120.2 | C12B—C11B—H11B | 120.1 |
C11A—C12A—C13A | 120.69 (12) | C11B—C12B—C13B | 120.11 (12) |
C11A—C12A—H12A | 119.7 | C11B—C12B—H12B | 119.9 |
C13A—C12A—H12A | 119.7 | C13B—C12B—H12B | 119.9 |
C14A—C13A—C12A | 119.85 (12) | C12B—C13B—C14B | 120.44 (11) |
C14A—C13A—C15A | 124.20 (12) | C12B—C13B—C15B | 122.76 (11) |
C12A—C13A—C15A | 115.92 (11) | C14B—C13B—C15B | 116.80 (11) |
C13A—C14A—C9A | 119.34 (12) | C9B—C14B—C13B | 119.13 (11) |
C13A—C14A—H14A | 120.3 | C9B—C14B—H14B | 120.4 |
C9A—C14A—H14A | 120.3 | C13B—C14B—H14B | 120.4 |
O2A—C15A—N3A | 122.35 (12) | O2B—C15B—N3B | 123.07 (11) |
O2A—C15A—C13A | 119.77 (12) | O2B—C15B—C13B | 121.40 (11) |
N3A—C15A—C13A | 117.87 (11) | N3B—C15B—C13B | 115.51 (11) |
N4A—C16A—N3A | 114.43 (11) | N4B—C16B—N3B | 115.10 (11) |
N4A—C16A—S2A | 127.03 (10) | N4B—C16B—S2B | 127.79 (10) |
N3A—C16A—S2A | 118.54 (9) | N3B—C16B—S2B | 117.11 (9) |
C22A—C17A—C18A | 120.25 (13) | C18B—C17B—C22B | 119.87 (12) |
C22A—C17A—N4A | 123.49 (12) | C18B—C17B—N4B | 124.05 (12) |
C18A—C17A—N4A | 116.05 (12) | C22B—C17B—N4B | 116.07 (12) |
C19A—C18A—C17A | 119.93 (14) | C17B—C18B—C19B | 119.62 (13) |
C19A—C18A—H18A | 120.0 | C17B—C18B—H18B | 120.2 |
C17A—C18A—H18A | 120.0 | C19B—C18B—H18B | 120.2 |
C20A—C19A—C18A | 120.28 (14) | C20B—C19B—C18B | 120.66 (13) |
C20A—C19A—H19A | 119.9 | C20B—C19B—H19B | 119.7 |
C18A—C19A—H19A | 119.9 | C18B—C19B—H19B | 119.7 |
C19A—C20A—C21A | 119.58 (13) | C19B—C20B—C21B | 119.51 (12) |
C19A—C20A—H20A | 120.2 | C19B—C20B—H20B | 120.2 |
C21A—C20A—H20A | 120.2 | C21B—C20B—H20B | 120.2 |
C22A—C21A—C20A | 120.86 (14) | C20B—C21B—C22B | 120.21 (13) |
C22A—C21A—H21A | 119.6 | C20B—C21B—H21B | 119.9 |
C20A—C21A—H21A | 119.6 | C22B—C21B—H21B | 119.9 |
C21A—C22A—C17A | 119.05 (13) | C21B—C22B—C17B | 120.00 (13) |
C21A—C22A—H22A | 120.5 | C21B—C22B—H22B | 120.0 |
C17A—C22A—H22A | 120.5 | C17B—C22B—H22B | 120.0 |
| | | |
C6A—C1A—C2A—C3A | 0.0 (2) | C6B—C1B—C2B—C3B | 0.1 (2) |
C1A—C2A—C3A—C4A | −0.1 (3) | C1B—C2B—C3B—C4B | −0.9 (3) |
C2A—C3A—C4A—C5A | 0.0 (3) | C2B—C3B—C4B—C5B | 0.8 (3) |
C3A—C4A—C5A—C6A | 0.3 (3) | C3B—C4B—C5B—C6B | 0.1 (2) |
C4A—C5A—C6A—C1A | −0.4 (2) | C2B—C1B—C6B—C5B | 0.9 (2) |
C4A—C5A—C6A—N1A | −179.49 (15) | C2B—C1B—C6B—N1B | 176.40 (14) |
C2A—C1A—C6A—C5A | 0.2 (2) | C4B—C5B—C6B—C1B | −1.0 (2) |
C2A—C1A—C6A—N1A | 179.43 (14) | C4B—C5B—C6B—N1B | −176.88 (14) |
C7A—N1A—C6A—C5A | −7.9 (2) | C7B—N1B—C6B—C1B | 25.2 (2) |
C7A—N1A—C6A—C1A | 172.97 (14) | C7B—N1B—C6B—C5B | −159.13 (15) |
C6A—N1A—C7A—N2A | 179.98 (13) | C6B—N1B—C7B—N2B | −174.40 (13) |
C6A—N1A—C7A—S1A | −0.6 (2) | C6B—N1B—C7B—S1B | 6.4 (2) |
C8A—N2A—C7A—N1A | 16.0 (2) | C8B—N2B—C7B—N1B | −4.6 (2) |
C8A—N2A—C7A—S1A | −163.55 (11) | C8B—N2B—C7B—S1B | 174.65 (11) |
C7A—N2A—C8A—O1A | −9.8 (2) | C7B—N2B—C8B—O1B | −8.0 (2) |
C7A—N2A—C8A—C9A | 170.61 (13) | C7B—N2B—C8B—C9B | 169.91 (12) |
O1A—C8A—C9A—C10A | 158.89 (14) | O1B—C8B—C9B—C14B | 132.42 (14) |
N2A—C8A—C9A—C10A | −21.56 (19) | N2B—C8B—C9B—C14B | −45.53 (18) |
O1A—C8A—C9A—C14A | −20.53 (19) | O1B—C8B—C9B—C10B | −40.45 (19) |
N2A—C8A—C9A—C14A | 159.02 (12) | N2B—C8B—C9B—C10B | 141.60 (13) |
C14A—C9A—C10A—C11A | −3.3 (2) | C14B—C9B—C10B—C11B | 1.9 (2) |
C8A—C9A—C10A—C11A | 177.33 (13) | C8B—C9B—C10B—C11B | 174.82 (13) |
C9A—C10A—C11A—C12A | 1.2 (2) | C9B—C10B—C11B—C12B | −3.6 (2) |
C10A—C11A—C12A—C13A | 1.9 (2) | C10B—C11B—C12B—C13B | 1.2 (2) |
C11A—C12A—C13A—C14A | −3.0 (2) | C11B—C12B—C13B—C14B | 2.8 (2) |
C11A—C12A—C13A—C15A | 179.14 (14) | C11B—C12B—C13B—C15B | −177.36 (13) |
C12A—C13A—C14A—C9A | 0.9 (2) | C10B—C9B—C14B—C13B | 2.1 (2) |
C15A—C13A—C14A—C9A | 178.63 (13) | C8B—C9B—C14B—C13B | −170.64 (12) |
C10A—C9A—C14A—C13A | 2.2 (2) | C12B—C13B—C14B—C9B | −4.50 (19) |
C8A—C9A—C14A—C13A | −178.41 (12) | C15B—C13B—C14B—C9B | 175.69 (12) |
C16A—N3A—C15A—O2A | 5.0 (2) | C16B—N3B—C15B—O2B | 13.1 (2) |
C16A—N3A—C15A—C13A | −175.77 (13) | C16B—N3B—C15B—C13B | −168.35 (12) |
C14A—C13A—C15A—O2A | −160.83 (14) | C12B—C13B—C15B—O2B | −153.15 (13) |
C12A—C13A—C15A—O2A | 17.0 (2) | C14B—C13B—C15B—O2B | 26.65 (18) |
C14A—C13A—C15A—N3A | 20.0 (2) | C12B—C13B—C15B—N3B | 28.24 (18) |
C12A—C13A—C15A—N3A | −162.26 (13) | C14B—C13B—C15B—N3B | −151.96 (12) |
C17A—N4A—C16A—N3A | 172.02 (13) | C17B—N4B—C16B—N3B | 167.44 (12) |
C17A—N4A—C16A—S2A | −7.3 (2) | C17B—N4B—C16B—S2B | −12.7 (2) |
C15A—N3A—C16A—N4A | −0.7 (2) | C15B—N3B—C16B—N4B | −13.00 (19) |
C15A—N3A—C16A—S2A | 178.72 (11) | C15B—N3B—C16B—S2B | 167.09 (11) |
C16A—N4A—C17A—C22A | −34.1 (2) | C16B—N4B—C17B—C18B | 39.0 (2) |
C16A—N4A—C17A—C18A | 151.23 (14) | C16B—N4B—C17B—C22B | −142.51 (14) |
C22A—C17A—C18A—C19A | 1.0 (2) | C22B—C17B—C18B—C19B | 2.7 (2) |
N4A—C17A—C18A—C19A | 175.86 (13) | N4B—C17B—C18B—C19B | −178.90 (13) |
C17A—C18A—C19A—C20A | 0.9 (2) | C17B—C18B—C19B—C20B | 0.7 (2) |
C18A—C19A—C20A—C21A | −1.8 (2) | C18B—C19B—C20B—C21B | −2.7 (2) |
C19A—C20A—C21A—C22A | 0.9 (2) | C19B—C20B—C21B—C22B | 1.3 (2) |
C20A—C21A—C22A—C17A | 1.0 (2) | C20B—C21B—C22B—C17B | 2.1 (2) |
C18A—C17A—C22A—C21A | −1.9 (2) | C18B—C17B—C22B—C21B | −4.1 (2) |
N4A—C17A—C22A—C21A | −176.41 (13) | N4B—C17B—C22B—C21B | 177.38 (13) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1NA···O1A | 0.83 (2) | 1.976 (19) | 2.6722 (16) | 140.9 (19) |
N2A—H2NA···S2Bi | 0.85 (2) | 2.59 (2) | 3.4201 (12) | 165.0 (19) |
N3A—H3NA···O2Bii | 0.864 (19) | 2.31 (2) | 2.9715 (15) | 133.3 (18) |
N4A—H4NA···O2A | 0.90 (2) | 1.86 (2) | 2.6064 (17) | 138.2 (18) |
N1B—H1NB···O1B | 0.86 (2) | 1.88 (2) | 2.6248 (17) | 144.5 (19) |
N2B—H2NB···S1Biii | 0.834 (19) | 2.71 (2) | 3.4961 (12) | 158.3 (19) |
N3B—H3NB···S1Ai | 0.84 (2) | 2.62 (2) | 3.4336 (12) | 163.0 (18) |
N4B—H4NB···O2B | 0.87 (2) | 1.92 (2) | 2.6543 (16) | 141.1 (19) |
C5A—H5AA···S1A | 0.95 | 2.51 | 3.1910 (16) | 129 |
C1B—H1BA···S1B | 0.95 | 2.68 | 3.2693 (15) | 121 |
C4B—H4BA···O2Aiv | 0.95 | 2.55 | 3.4819 (18) | 165 |
C10B—H10B···S2Av | 0.95 | 2.84 | 3.4570 (15) | 123 |
C11B—H11B···S2Av | 0.95 | 2.85 | 3.4687 (15) | 123 |
C14A—H14A···O2Bii | 0.95 | 2.35 | 3.2700 (17) | 164 |
C14B—H14B···O1Aii | 0.95 | 2.36 | 3.2897 (17) | 165 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1, −y+1, −z; (iii) −x, −y+1, −z; (iv) −x+1, −y+1, −z+1; (v) x−1, y+1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1NA···O1A | 0.83 (2) | 1.976 (19) | 2.6722 (16) | 140.9 (19) |
N2A—H2NA···S2Bi | 0.85 (2) | 2.59 (2) | 3.4201 (12) | 165.0 (19) |
N3A—H3NA···O2Bii | 0.864 (19) | 2.31 (2) | 2.9715 (15) | 133.3 (18) |
N4A—H4NA···O2A | 0.90 (2) | 1.86 (2) | 2.6064 (17) | 138.2 (18) |
N1B—H1NB···O1B | 0.86 (2) | 1.88 (2) | 2.6248 (17) | 144.5 (19) |
N2B—H2NB···S1Biii | 0.834 (19) | 2.71 (2) | 3.4961 (12) | 158.3 (19) |
N3B—H3NB···S1Ai | 0.84 (2) | 2.62 (2) | 3.4336 (12) | 163.0 (18) |
N4B—H4NB···O2B | 0.87 (2) | 1.92 (2) | 2.6543 (16) | 141.1 (19) |
C5A—H5AA···S1A | 0.95 | 2.51 | 3.1910 (16) | 129 |
C1B—H1BA···S1B | 0.95 | 2.68 | 3.2693 (15) | 121 |
C4B—H4BA···O2Aiv | 0.95 | 2.55 | 3.4819 (18) | 165 |
C10B—H10B···S2Av | 0.95 | 2.84 | 3.4570 (15) | 123 |
C11B—H11B···S2Av | 0.95 | 2.85 | 3.4687 (15) | 123 |
C14A—H14A···O2Bii | 0.95 | 2.35 | 3.2700 (17) | 164 |
C14B—H14B···O1Aii | 0.95 | 2.36 | 3.2897 (17) | 165 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1, −y+1, −z; (iii) −x, −y+1, −z; (iv) −x+1, −y+1, −z+1; (v) x−1, y+1, z. |
Thiourea derivatives play an important roles in many biological activities (Madan et al., 1991) such as antimycobacterial agent (Fernandez et al., 2005), antiviral (Kucukguzel et al., 2008), and antibacterial (Saeed et al., 2009). As part of our studies in this area, we now describe the title compound, which contains two thiourea groups from the reaction of 3-acetylbenzoyl isothiocyanate with aniline.
There are two molecules in the asymmetric unit (Fig. 1) of the title compound. For molecule A, the dihedral angles between the aldehyde benzene (C9A—C14A) and the phenyl rings (C1A—C6A & C17A—C22A) are 16.97 (8) and 20.97 (8)°, respectively while the two phenyl rings make a dihedral angle of 37.87 (8)°. In the molecule B, corresponding values are 34.92 (7), 53.90 (7)° and 60.68 (8)° respectively.
In each molecule, three set of S(6) hydrogen rings motif can be observe involving the N—H···O and C—H···S intramolecular interactions. An extensive intermolceular interactions of N—H···S, N—H···O, C—H···O and C—H···S link the molecules into a three-dimensional network (Fig. 2, Table 1).