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The molecules of the title compound, C
11H
9N
3O
2S, 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.
Supporting information
CCDC reference: 643648
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (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
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
top
Crystal data top
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) Å3 | 0.58 × 0.56 × 0.12 mm |
Z = 2 | |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0738P)2 + 0.1955P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O31i | 1.02 | 2.22 | 3.180 (2) | 155 |
N1—H1···O32i | 1.02 | 2.55 | 3.457 (3) | 148 |
C6—H6···O32i | 0.95 | 2.39 | 3.281 (3) | 157 |
C16—H16···O31i | 0.95 | 2.58 | 3.425 (3) | 148 |
Symmetry code: (i) x−1, y+1, z. |
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