1-[1-(3-Nitro­phen­yl)ethyl­idene]thio­semicarbazide

The title compound, C₉H₁₀N₄O₂S, was prepared by the reaction of thio­semicarbazide with 1-(3-nitro­phen­yl)ethanone at room temperature. The crystal packing is stabilized by van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.079
• wR factor = 0.257
• Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.257
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.118
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT084_ALERT_2_C High R2 Value ..................................       0.26
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C8
PLAT414_ALERT_2_C Short Intra D-H..H-X       H3A    ..  H8A     ..       1.90 Ang.

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           26.96
           From the CIF: _reflns_number_total               2345
           From the CIF: _diffrn_reflns_limit_ max hkl   16.    0.   23.
           From the CIF: _diffrn_reflns_limit_ min hkl    0.   -9.  -23.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl   17.   10.   25.
           Calculated minimum hkl  -17.  -10.  -25.
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

1-[1-(3-Nitrophenyl)ethylidene]thiosemicarbazide

Crystal data

C9H10N4O2S	F(000) = 992
Mr = 238.27	Dx = 1.438 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 13.756 (3) Å	θ = 4–14°
b = 8.0690 (16) Å	µ = 0.29 mm^−1
c = 19.835 (4) Å	T = 293 K
V = 2201.6 (8) Å^3	Block, yellow
Z = 8	0.25 × 0.20 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.118
Radiation source: fine-focus sealed tube	θmax = 27.0°, θmin = 2.1°
Graphite monochromator	h = 0→16
ω scans	k = −9→0
4617 measured reflections	l = −23→23
2345 independent reflections	3 standard reflections every 100 reflections
1172 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.257	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.1483P)^2] where P = (Fo^2 + 2Fc^2)/3
2345 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.69 e Å^−3
0 restraints	Δρmin = −0.81 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	−0.27745 (9)	0.20648 (14)	0.28109 (6)	0.0384 (4)
O1	0.4597 (3)	0.4038 (6)	0.4336 (2)	0.0782 (15)
O2	0.3978 (3)	0.4932 (6)	0.3416 (2)	0.0716 (14)
N1	0.3893 (3)	0.4375 (5)	0.3992 (3)	0.0488 (12)
N2	−0.0339 (3)	0.3218 (5)	0.3719 (2)	0.0405 (10)
N3	−0.1182 (3)	0.3349 (5)	0.3340 (2)	0.0404 (11)
H3A	−0.1358	0.4281	0.3168	0.048*
N4	−0.1378 (3)	0.0566 (5)	0.3499 (2)	0.0433 (11)
H4A	−0.0833	0.0555	0.3711	0.052*
H4B	−0.1702	−0.0336	0.3449	0.052*
C1	0.2916 (4)	0.4071 (6)	0.4247 (3)	0.0395 (12)
C2	0.2818 (5)	0.3428 (7)	0.4888 (3)	0.0547 (15)
H2B	0.3360	0.3205	0.5153	0.066*
C3	0.1877 (5)	0.3123 (9)	0.5126 (3)	0.0657 (19)
H3B	0.1787	0.2702	0.5558	0.079*
C4	0.1091 (4)	0.3440 (7)	0.4728 (3)	0.0518 (15)
H4C	0.0471	0.3227	0.4892	0.062*
C5	0.1198 (4)	0.4079 (6)	0.4077 (2)	0.0385 (12)
C6	0.2124 (4)	0.4421 (6)	0.3839 (2)	0.0350 (11)
H6A	0.2213	0.4878	0.3413	0.042*
C7	0.0326 (4)	0.4315 (6)	0.3642 (2)	0.0365 (11)
C8	0.0283 (4)	0.5733 (7)	0.3148 (3)	0.0512 (15)
H8A	−0.0327	0.5706	0.2912	0.077*
H8B	0.0806	0.5632	0.2830	0.077*
H8C	0.0342	0.6763	0.3386	0.077*
C9	−0.1716 (3)	0.1970 (5)	0.3249 (2)	0.0317 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0404 (7)	0.0284 (6)	0.0462 (8)	−0.0011 (5)	−0.0082 (6)	−0.0029 (5)
O1	0.044 (3)	0.114 (4)	0.076 (3)	0.005 (2)	−0.013 (3)	0.020 (3)
O2	0.064 (3)	0.092 (3)	0.058 (3)	−0.011 (2)	0.007 (2)	0.023 (3)
N1	0.048 (3)	0.046 (3)	0.052 (3)	0.003 (2)	−0.001 (2)	−0.001 (2)
N2	0.040 (2)	0.036 (2)	0.045 (3)	−0.006 (2)	−0.011 (2)	−0.0002 (19)
N3	0.043 (2)	0.028 (2)	0.051 (3)	−0.0030 (18)	−0.011 (2)	0.0020 (18)
N4	0.048 (3)	0.029 (2)	0.052 (3)	−0.0007 (19)	−0.018 (2)	0.0025 (19)
C1	0.043 (3)	0.038 (3)	0.037 (3)	−0.002 (2)	−0.007 (2)	−0.007 (2)
C2	0.054 (4)	0.071 (4)	0.039 (3)	−0.006 (3)	−0.015 (3)	0.005 (3)
C3	0.068 (4)	0.097 (5)	0.032 (3)	−0.009 (4)	−0.002 (3)	0.018 (3)
C4	0.052 (4)	0.067 (4)	0.036 (3)	−0.017 (3)	0.006 (3)	0.008 (3)
C5	0.047 (3)	0.035 (3)	0.033 (3)	−0.009 (2)	−0.003 (2)	−0.007 (2)
C6	0.045 (3)	0.033 (2)	0.027 (2)	−0.006 (2)	0.001 (2)	−0.0001 (19)
C7	0.037 (3)	0.036 (3)	0.036 (3)	−0.003 (2)	0.002 (2)	−0.004 (2)
C8	0.044 (3)	0.056 (3)	0.054 (4)	−0.012 (3)	−0.005 (3)	0.020 (3)
C9	0.032 (3)	0.031 (3)	0.033 (3)	−0.002 (2)	0.002 (2)	−0.003 (2)

Geometric parameters (Å, º)

S1—C9	1.698 (5)	C2—C3	1.400 (8)
O1—N1	1.216 (6)	C2—H2B	0.9300
O2—N1	1.233 (6)	C3—C4	1.363 (8)
N1—C1	1.458 (7)	C3—H3B	0.9300
N2—C7	1.282 (6)	C4—C5	1.398 (7)
N2—N3	1.387 (5)	C4—H4C	0.9300
N3—C9	1.345 (6)	C5—C6	1.387 (7)
N3—H3A	0.8600	C5—C7	1.490 (7)
N4—C9	1.321 (6)	C6—H6A	0.9300
N4—H4A	0.8600	C7—C8	1.508 (7)
N4—H4B	0.8600	C8—H8A	0.9600
C1—C2	1.379 (7)	C8—H8B	0.9600
C1—C6	1.386 (7)	C8—H8C	0.9600
O1—N1—O2	121.8 (5)	C3—C4—H4C	119.3
O1—N1—C1	120.1 (5)	C5—C4—H4C	119.3
O2—N1—C1	118.1 (5)	C6—C5—C4	119.0 (5)
C7—N2—N3	118.6 (4)	C6—C5—C7	121.2 (5)
C9—N3—N2	117.8 (4)	C4—C5—C7	119.8 (5)
C9—N3—H3A	121.1	C1—C6—C5	118.8 (4)
N2—N3—H3A	121.1	C1—C6—H6A	120.6
C9—N4—H4A	120.0	C5—C6—H6A	120.6
C9—N4—H4B	120.0	N2—C7—C5	114.7 (4)
H4A—N4—H4B	120.0	N2—C7—C8	125.0 (5)
C2—C1—C6	122.6 (5)	C5—C7—C8	120.3 (4)
C2—C1—N1	118.3 (5)	C7—C8—H8A	109.5
C6—C1—N1	119.1 (5)	C7—C8—H8B	109.5
C1—C2—C3	117.8 (6)	H8A—C8—H8B	109.5
C1—C2—H2B	121.1	C7—C8—H8C	109.5
C3—C2—H2B	121.1	H8A—C8—H8C	109.5
C4—C3—C2	120.3 (5)	H8B—C8—H8C	109.5
C4—C3—H3B	119.8	N4—C9—N3	117.9 (4)
C2—C3—H3B	119.8	N4—C9—S1	122.2 (4)
C3—C4—C5	121.4 (5)	N3—C9—S1	120.0 (3)