Thio­phene-2-carbaldehyde 3-nitro­phenyl­hydrazone

The mol­ecules of the title compound, C₁₁H₉N₃O₂S, are nearly planar in the solid state. They are linked into complex chains of rings, generated by translation and utilizing a cooperative combination of two N—H...O hydrogen bonds and two C—H...O hydrogen bonds. One hydrogen bond of each type has dimensions indicating that it is reasonably strong for its type, while the other is much weaker. There are no significant inter­actions between neighbouring chains.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.105
• Data-to-parameter ratio = 29.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT021_ALERT_1_B Ratio Unique / Expected Reflections too High ...       3.11
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.94

Alert level C
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C14    -   C15     ..       5.36 su
PLAT353_ALERT_3_C Long    N-H Bond (0.87A)   N1     -   H1     ...       1.02 Ang.

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

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

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Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: FLIPPER (Oszlányi & Sütő, 2004, 2005; Spek, 2003); program(s) used to refine structure: OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Thiophene-2-carbaldehyde 3-nitrophenylhydrazone

Crystal data

C11H9N3O2S	F(000) = 256
Mr = 247.27	Dx = 1.419 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1437 reflections
a = 5.9309 (3) Å	θ = 2.9–27.5°
b = 5.6529 (3) Å	µ = 0.27 mm^−1
c = 17.2697 (10) Å	T = 120 K
β = 91.762 (2)°	Lath, red
V = 578.72 (5) Å^3	0.58 × 0.56 × 0.12 mm
Z = 2

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	4606 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	4462 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 9.091 pixels mm^-1	θmax = 27.6°, θmin = 3.4°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −7→7
Tmin = 0.858, Tmax = 0.968	l = −22→22
1476 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.0738P)^2 + 0.1955P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
4606 reflections	Δρmax = 0.35 e Å^−3
155 parameters	Δρmin = −0.54 e Å^−3
1 restraint	Absolute structure: Flack (1983), with 1213 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.13 (8)

Special details

Experimental. IR (KBr, ν, cm^-1): 3305, 3039, 1621, 1588, 1551, 1521, 1474, 1445, 1426, 1342, 1342, 1314, 1269, 1219, 1131, 1071, 1044, 990, 916, 873, 823, 795, 757, 735, 716, 695, 668, 576, 550, 503.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S11	0.56083 (8)	0.31170 (10)	0.38339 (2)	0.02200 (13)
C12	0.4070 (3)	0.5582 (4)	0.35649 (9)	0.0174 (4)
C13	0.2053 (3)	0.5703 (5)	0.39530 (10)	0.0208 (5)
C14	0.1813 (4)	0.3735 (5)	0.44669 (10)	0.0287 (6)
C15	0.3567 (4)	0.2239 (5)	0.44633 (10)	0.0270 (5)
C16	0.4823 (3)	0.7230 (4)	0.29830 (8)	0.0160 (4)
N2	0.6657 (3)	0.6796 (3)	0.26232 (7)	0.0160 (4)
N1	0.7228 (3)	0.8380 (4)	0.20659 (8)	0.0184 (4)
C1	0.9074 (3)	0.7892 (4)	0.16153 (8)	0.0139 (4)
C2	1.0462 (3)	0.5963 (4)	0.17622 (9)	0.0147 (4)
C3	1.2314 (3)	0.5638 (4)	0.12975 (9)	0.0152 (4)
N13	1.3801 (3)	0.3631 (3)	0.14586 (8)	0.0198 (4)
O31	1.3376 (2)	0.2294 (3)	0.19990 (7)	0.0241 (4)
O32	1.5444 (2)	0.3337 (4)	0.10471 (7)	0.0304 (4)
C4	1.2832 (3)	0.7141 (4)	0.06886 (9)	0.0164 (4)
C5	1.1394 (3)	0.9022 (4)	0.05429 (9)	0.0177 (4)
C6	0.9536 (3)	0.9439 (4)	0.09963 (9)	0.0158 (4)
H13	0.0973	0.6932	0.3886	0.025*
H14	0.0539	0.3512	0.4779	0.034*
H15	0.3674	0.0852	0.4773	0.032*
H16	0.3975	0.8618	0.2867	0.019*
H1	0.6360	0.9917	0.1966	0.022*
H2	1.0159	0.4890	0.2169	0.018*
H4	1.4120	0.6882	0.0386	0.020*
H5	1.1681	1.0055	0.0123	0.021*
H6	0.8582	1.0757	0.0891	0.019*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S11	0.0270 (2)	0.0206 (3)	0.01830 (16)	0.0035 (3)	−0.00027 (16)	0.0011 (2)
C12	0.0202 (9)	0.0183 (11)	0.0134 (6)	0.0032 (10)	−0.0018 (7)	−0.0019 (7)
C13	0.0195 (10)	0.0245 (13)	0.0187 (7)	0.0015 (10)	0.0040 (7)	0.0031 (8)
C14	0.0245 (11)	0.0389 (17)	0.0230 (8)	−0.0062 (11)	0.0052 (8)	0.0066 (9)
C15	0.0383 (12)	0.0270 (13)	0.0156 (8)	−0.0110 (11)	−0.0012 (8)	0.0072 (8)
C16	0.0191 (9)	0.0160 (11)	0.0130 (7)	0.0022 (9)	0.0006 (7)	−0.0023 (7)
N2	0.0179 (8)	0.0160 (10)	0.0143 (6)	0.0017 (8)	0.0015 (6)	0.0031 (6)
N1	0.0189 (7)	0.0183 (11)	0.0184 (6)	0.0048 (9)	0.0067 (6)	0.0062 (7)
C1	0.0122 (8)	0.0159 (11)	0.0135 (6)	0.0003 (10)	−0.0009 (6)	0.0010 (7)
C2	0.0180 (9)	0.0131 (11)	0.0131 (6)	0.0030 (9)	0.0000 (7)	0.0002 (7)
C3	0.0154 (9)	0.0150 (11)	0.0150 (7)	0.0032 (9)	−0.0019 (7)	−0.0032 (7)
N13	0.0205 (8)	0.0192 (11)	0.0194 (6)	0.0054 (8)	−0.0034 (6)	−0.0063 (7)
O31	0.0315 (8)	0.0204 (9)	0.0204 (6)	0.0078 (7)	−0.0020 (5)	0.0012 (6)
O32	0.0253 (7)	0.0331 (11)	0.0334 (6)	0.0142 (9)	0.0098 (6)	−0.0026 (8)
C4	0.0151 (9)	0.0194 (12)	0.0147 (7)	0.0015 (9)	0.0019 (7)	−0.0011 (7)
C5	0.0162 (9)	0.0205 (12)	0.0164 (7)	−0.0025 (9)	0.0016 (7)	0.0011 (7)
C6	0.0170 (9)	0.0124 (10)	0.0179 (7)	0.0037 (9)	−0.0010 (7)	0.0005 (7)

Geometric parameters (Å, º)

S11—C12	1.722 (2)	C1—C2	1.385 (3)
S11—C15	1.725 (2)	C1—C6	1.414 (3)
C12—C13	1.391 (3)	C2—C3	1.392 (2)
C12—C16	1.451 (3)	C2—H2	0.95
C13—C14	1.433 (3)	C3—C4	1.393 (3)
C13—H13	0.95	C3—N13	1.459 (3)
C14—C15	1.341 (3)	N13—O31	1.233 (2)
C14—H14	0.95	N13—O32	1.235 (2)
C15—H15	0.95	C4—C5	1.381 (3)
C16—N2	1.293 (2)	C4—H4	0.95
C16—H16	0.95	C5—C6	1.392 (3)
N2—N1	1.365 (2)	C5—H5	0.95
N1—C1	1.390 (2)	C6—H6	0.95
N1—H1	1.02
C12—S11—C15	91.52 (11)	C2—C1—C6	119.81 (15)
C13—C12—C16	126.18 (19)	N1—C1—C6	118.35 (19)
C13—C12—S11	111.47 (16)	C1—C2—C3	118.24 (17)
C16—C12—S11	122.32 (14)	C1—C2—H2	120.9
C12—C13—C14	111.3 (2)	C3—C2—H2	120.9
C12—C13—H13	124.3	C2—C3—C4	123.43 (19)
C14—C13—H13	124.3	C2—C3—N13	118.39 (17)
C15—C14—C13	113.25 (18)	C4—C3—N13	118.17 (16)
C15—C14—H14	123.4	O31—N13—O32	122.45 (18)
C13—C14—H14	123.4	O31—N13—C3	119.00 (15)
C14—C15—S11	112.41 (17)	O32—N13—C3	118.56 (17)
C14—C15—H15	123.8	C5—C4—C3	117.24 (16)
S11—C15—H15	123.8	C5—C4—H4	121.4
N2—C16—C12	119.53 (19)	C3—C4—H4	121.4
N2—C16—H16	120.2	C4—C5—C6	121.53 (18)
C12—C16—H16	120.2	C4—C5—H5	119.2
C16—N2—N1	116.44 (17)	C6—C5—H5	119.2
N2—N1—C1	118.77 (17)	C5—C6—C1	119.73 (18)
N2—N1—H1	122.8	C5—C6—H6	120.1
C1—N1—H1	118.4	C1—C6—H6	120.1
C2—C1—N1	121.84 (17)
C15—S11—C12—C13	0.05 (16)	C6—C1—C2—C3	1.2 (3)
C15—S11—C12—C16	−177.96 (16)	C1—C2—C3—C4	−0.6 (3)
C16—C12—C13—C14	177.70 (18)	C1—C2—C3—N13	179.00 (16)
S11—C12—C13—C14	−0.2 (2)	C2—C3—N13—O31	−0.1 (2)
C12—C13—C14—C15	0.3 (3)	C4—C3—N13—O31	179.49 (17)
C13—C14—C15—S11	−0.3 (2)	C2—C3—N13—O32	179.94 (17)
C12—S11—C15—C14	0.14 (16)	C4—C3—N13—O32	−0.5 (3)
C13—C12—C16—N2	−174.37 (18)	C2—C3—C4—C5	−0.8 (3)
S11—C12—C16—N2	3.3 (2)	N13—C3—C4—C5	179.61 (16)
C12—C16—N2—N1	177.98 (16)	C3—C4—C5—C6	1.6 (3)
C16—N2—N1—C1	−174.47 (16)	C4—C5—C6—C1	−0.9 (3)
N2—N1—C1—C2	−6.0 (3)	C2—C1—C6—C5	−0.5 (3)
N2—N1—C1—C6	174.64 (18)	N1—C1—C6—C5	178.89 (17)
N1—C1—C2—C3	−178.16 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O31^i	1.02	2.22	3.180 (2)	155
N1—H1···O32^i	1.02	2.55	3.457 (3)	148
C6—H6···O32^i	0.95	2.39	3.281 (3)	157
C16—H16···O31^i	0.95	2.58	3.425 (3)	148

Symmetry code: (i) x−1, y+1, z.