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organic compounds
In the title structure, C16H12N4O3·0.5H2O, the uncoordinated water molecule lies on a special position of site symmetry 2; O—HO and N—HO hydrogen bonds link the water and organic molecules into a layer structure.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030266/lh6504sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030266/lh6504Isup2.hkl |
CCDC reference: 289797
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.051
- wR factor = 0.174
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
1H-Indole-3-carbaldehyde 2-nitrophenylhydrazone hemihydrate top
Crystal data top
C16H12N4O3·0.5H2O | F(000) = 1320 |
Mr = 317.30 | Dx = 1.451 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1977 reflections |
a = 28.983 (2) Å | θ = 2.3–23.7° |
b = 6.0809 (5) Å | µ = 0.11 mm−1 |
c = 16.559 (1) Å | T = 295 K |
β = 95.397 (2)° | Block, orange red |
V = 2905.5 (4) Å3 | 0.26 × 0.23 × 0.16 mm |
Z = 8 |
Data collection top
Bruker SMART area-detector diffractometer | 1720 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.039 |
Graphite monochromator | θmax = 27.1°, θmin = 1.4° |
φ and ω scans | h = −30→36 |
8682 measured reflections | k = −7→7 |
3167 independent reflections | l = −21→18 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.174 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0931P)2] where P = (Fo2 + 2Fc2)/3 |
3167 reflections | (Δ/σ)max = 0.001 |
213 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.54 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.3933 (1) | 0.3877 (3) | 0.6805 (1) | 0.0707 (7) | |
O2 | 0.4479 (1) | 0.6019 (3) | 0.6516 (1) | 0.0547 (5) | |
O3 | 0.4577 (1) | 1.0832 (3) | 0.5732 (1) | 0.0534 (5) | |
O1w | 0.5000 | 0.2367 (6) | 0.7500 | 0.0851 (10) | |
N1 | 0.4071 (1) | 0.5530 (4) | 0.6488 (1) | 0.0442 (6) | |
N2 | 0.4527 (1) | 0.7976 (3) | 0.4874 (1) | 0.0438 (6) | |
N3 | 0.4259 (1) | 0.6299 (3) | 0.4508 (1) | 0.0420 (5) | |
N4 | 0.4166 (1) | 0.0103 (4) | 0.2927 (1) | 0.0498 (6) | |
C1 | 0.3872 (1) | 0.8766 (4) | 0.5626 (2) | 0.0400 (6) | |
C2 | 0.3728 (1) | 0.7014 (4) | 0.6076 (2) | 0.0394 (6) | |
C3 | 0.3271 (1) | 0.6636 (5) | 0.6181 (2) | 0.0522 (7) | |
C4 | 0.2942 (1) | 0.8030 (6) | 0.5831 (2) | 0.0624 (9) | |
C5 | 0.3070 (1) | 0.9786 (6) | 0.5399 (2) | 0.070 (1) | |
C6 | 0.3529 (1) | 1.0171 (5) | 0.5297 (2) | 0.0591 (8) | |
C7 | 0.4358 (1) | 0.9255 (4) | 0.5432 (2) | 0.0408 (6) | |
C8 | 0.4477 (1) | 0.5011 (4) | 0.4068 (2) | 0.0418 (6) | |
C9 | 0.4251 (1) | 0.3234 (4) | 0.3624 (2) | 0.0399 (6) | |
C10 | 0.4475 (1) | 0.1578 (4) | 0.3267 (2) | 0.0455 (7) | |
C11 | 0.3765 (1) | 0.2756 (4) | 0.3487 (1) | 0.0387 (6) | |
C12 | 0.3727 (1) | 0.0749 (4) | 0.3058 (2) | 0.0439 (6) | |
C13 | 0.3303 (1) | −0.0240 (5) | 0.2832 (2) | 0.0553 (7) | |
C14 | 0.2912 (1) | 0.0828 (5) | 0.3036 (2) | 0.0608 (8) | |
C15 | 0.2938 (1) | 0.2818 (5) | 0.3443 (2) | 0.0574 (8) | |
C16 | 0.3357 (1) | 0.3806 (4) | 0.3673 (2) | 0.0473 (7) | |
H1w | 0.4950 | 0.3266 | 0.7095 | 0.102* | |
H2n | 0.4803 | 0.8193 | 0.4742 | 0.053* | |
H4n | 0.4235 | −0.1060 | 0.2668 | 0.060* | |
H3 | 0.3187 | 0.5444 | 0.6487 | 0.063* | |
H4 | 0.2630 | 0.7776 | 0.5889 | 0.075* | |
H5 | 0.2844 | 1.0744 | 0.5169 | 0.083* | |
H6 | 0.3610 | 1.1392 | 0.5003 | 0.071* | |
H8 | 0.4792 | 0.5234 | 0.4036 | 0.050* | |
H10 | 0.4795 | 0.1477 | 0.3259 | 0.055* | |
H13 | 0.3284 | −0.1571 | 0.2555 | 0.066* | |
H14 | 0.2623 | 0.0198 | 0.2896 | 0.073* | |
H15 | 0.2666 | 0.3504 | 0.3563 | 0.069* | |
H16 | 0.3370 | 0.5144 | 0.3946 | 0.057* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.066 (1) | 0.050 (1) | 0.099 (2) | 0.004 (1) | 0.026 (1) | 0.024 (1) |
O2 | 0.039 (1) | 0.059 (1) | 0.066 (1) | 0.002 (1) | 0.008 (1) | 0.011 (1) |
O3 | 0.053 (1) | 0.050 (1) | 0.059 (1) | −0.010 (1) | 0.014 (1) | −0.015 (1) |
O1w | 0.087 (2) | 0.08 (2) | 0.091 (2) | 0.000 | 0.018 (2) | 0.000 |
N1 | 0.044 (1) | 0.041 (1) | 0.050 (1) | 0.003 (1) | 0.014 (1) | 0.001 (1) |
N2 | 0.042 (1) | 0.044 (1) | 0.048 (1) | −0.009 (1) | 0.016 (1) | −0.007 (1) |
N3 | 0.047 (1) | 0.037 (1) | 0.043 (1) | −0.007 (1) | 0.010 (1) | −0.004 (1) |
N4 | 0.053 (1) | 0.041 (1) | 0.056 (2) | 0.006 (1) | 0.010 (1) | −0.011 (1) |
C1 | 0.042 (1) | 0.044 (2) | 0.035 (1) | 0.002 (1) | 0.009 (1) | −0.004 (1) |
C2 | 0.038 (1) | 0.041 (2) | 0.040 (1) | 0.000 (1) | 0.007 (1) | −0.006 (1) |
C3 | 0.042 (2) | 0.059 (2) | 0.057 (2) | −0.005 (1) | 0.013 (1) | −0.001 (1) |
C4 | 0.037 (2) | 0.087 (2) | 0.064 (2) | 0.004 (2) | 0.011 (1) | −0.001 (2) |
C5 | 0.050 (2) | 0.099 (3) | 0.059 (2) | 0.029 (2) | 0.004 (2) | 0.014 (2) |
C6 | 0.058 (2) | 0.071 (2) | 0.051 (2) | 0.016 (2) | 0.015 (1) | 0.014 (2) |
C7 | 0.045 (2) | 0.040 (2) | 0.038 (1) | −0.001 (1) | 0.009 (1) | 0.000 (1) |
C8 | 0.041 (1) | 0.043 (2) | 0.043 (2) | −0.001 (1) | 0.010 (1) | 0.000 (1) |
C9 | 0.043 (1) | 0.038 (2) | 0.040 (1) | 0.002 (1) | 0.009 (1) | 0.000 (1) |
C10 | 0.041 (2) | 0.047 (2) | 0.049 (2) | 0.004 (1) | 0.008 (1) | −0.004 (1) |
C11 | 0.045 (2) | 0.035 (1) | 0.038 (1) | 0.005 (1) | 0.008 (1) | 0.004 (1) |
C12 | 0.048 (2) | 0.042 (2) | 0.042 (2) | 0.002 (1) | 0.007 (1) | 0.003 (1) |
C13 | 0.059 (2) | 0.052 (2) | 0.055 (2) | −0.009 (1) | 0.006 (1) | −0.004 (1) |
C14 | 0.047 (2) | 0.074 (2) | 0.061 (2) | −0.008 (2) | 0.002 (1) | 0.004 (2) |
C15 | 0.049 (2) | 0.068 (2) | 0.056 (2) | 0.011 (2) | 0.009 (1) | 0.003 (2) |
C16 | 0.049 (2) | 0.045 (2) | 0.048 (2) | 0.010 (1) | 0.009 (1) | 0.004 (1) |
Geometric parameters (Å, º) top
O1—N1 | 1.219 (3) | C11—C16 | 1.401 (3) |
O2—N1 | 1.216 (2) | C11—C12 | 1.411 (3) |
O3—C7 | 1.230 (3) | C12—C13 | 1.387 (4) |
N1—C2 | 1.463 (3) | C13—C14 | 1.375 (4) |
N2—C7 | 1.335 (3) | C14—C15 | 1.383 (4) |
N2—N3 | 1.386 (3) | C15—C16 | 1.377 (4) |
N3—C8 | 1.277 (3) | O1w—H1w | 0.87 |
N4—C10 | 1.352 (3) | N2—H2n | 0.86 |
N4—C12 | 1.370 (3) | N4—H4n | 0.86 |
C1—C6 | 1.383 (4) | C3—H3 | 0.93 |
C1—C2 | 1.387 (3) | C4—H4 | 0.93 |
C1—C7 | 1.501 (3) | C5—H5 | 0.93 |
C2—C3 | 1.371 (3) | C6—H6 | 0.93 |
C3—C4 | 1.365 (4) | C8—H8 | 0.93 |
C4—C5 | 1.356 (4) | C10—H10 | 0.93 |
C5—C6 | 1.379 (4) | C13—H13 | 0.93 |
C8—C9 | 1.432 (3) | C14—H14 | 0.93 |
C9—C10 | 1.363 (3) | C15—H15 | 0.93 |
C9—C11 | 1.436 (3) | C16—H16 | 0.93 |
O2—N1—O1 | 122.9 (2) | C13—C12—C11 | 122.4 (2) |
O2—N1—C2 | 118.9 (2) | C14—C13—C12 | 117.3 (3) |
O1—N1—C2 | 118.2 (2) | C13—C14—C15 | 121.6 (3) |
C7—N2—N3 | 120.2 (2) | C16—C15—C14 | 121.5 (3) |
C8—N3—N2 | 114.4 (2) | C15—C16—C11 | 118.7 (3) |
C10—N4—C12 | 109.4 (2) | C7—N2—H2n | 119.9 |
C6—C1—C2 | 116.3 (2) | N3—N2—H2n | 119.9 |
C6—C1—C7 | 116.5 (2) | C10—N4—H4n | 125.3 |
C2—C1—C7 | 127.1 (2) | C12—N4—H4n | 125.3 |
C3—C2—C1 | 122.8 (3) | C4—C3—H3 | 120.4 |
C3—C2—N1 | 117.3 (2) | C2—C3—H3 | 120.4 |
C1—C2—N1 | 119.9 (2) | C5—C4—H4 | 120.1 |
C4—C3—C2 | 119.2 (3) | C3—C4—H4 | 120.1 |
C5—C4—C3 | 119.9 (3) | C4—C5—H5 | 119.6 |
C4—C5—C6 | 120.9 (3) | C6—C5—H5 | 119.6 |
C5—C6—C1 | 121.0 (3) | C5—C6—H6 | 119.5 |
O3—C7—N2 | 121.6 (2) | C1—C6—H6 | 119.5 |
O3—C7—C1 | 121.8 (2) | N3—C8—H8 | 119.0 |
N2—C7—C1 | 116.5 (2) | C9—C8—H8 | 119.0 |
N3—C8—C9 | 121.9 (2) | N4—C10—H10 | 124.9 |
C10—C9—C8 | 124.5 (2) | C9—C10—H10 | 124.9 |
C10—C9—C11 | 106.4 (2) | C14—C13—H13 | 121.3 |
C8—C9—C11 | 129.0 (2) | C12—C13—H13 | 121.3 |
N4—C10—C9 | 110.3 (2) | C13—C14—H14 | 119.2 |
C16—C11—C12 | 118.5 (2) | C15—C14—H14 | 119.2 |
C16—C11—C9 | 135.0 (2) | C16—C15—H15 | 119.2 |
C12—C11—C9 | 106.4 (2) | C14—C15—H15 | 119.2 |
N4—C12—C13 | 130.3 (3) | C15—C16—H16 | 120.7 |
N4—C12—C11 | 107.4 (2) | C11—C16—H16 | 120.7 |
C7—N2—N3—C8 | −171.2 (2) | N3—C8—C9—C10 | −167.5 (2) |
C6—C1—C2—C3 | 1.4 (4) | N3—C8—C9—C11 | 9.7 (4) |
C7—C1—C2—C3 | −176.1 (2) | C12—N4—C10—C9 | −0.5 (3) |
C6—C1—C2—N1 | −176.1 (2) | C8—C9—C10—N4 | 177.2 (2) |
C7—C1—C2—N1 | 6.4 (4) | C11—C9—C10—N4 | −0.6 (3) |
O2—N1—C2—C3 | −168.3 (2) | C10—C9—C11—C16 | −178.0 (3) |
O1—N1—C2—C3 | 10.1 (3) | C8—C9—C11—C16 | 4.3 (5) |
O2—N1—C2—C1 | 9.4 (3) | C10—C9—C11—C12 | 1.4 (3) |
O1—N1—C2—C1 | −172.2 (2) | C8—C9—C11—C12 | −176.3 (2) |
C1—C2—C3—C4 | 0.1 (4) | C10—N4—C12—C13 | −179.3 (3) |
N1—C2—C3—C4 | 177.6 (2) | C10—N4—C12—C11 | 1.4 (3) |
C2—C3—C4—C5 | −1.3 (4) | C16—C11—C12—N4 | 177.9 (2) |
C3—C4—C5—C6 | 1.0 (5) | C9—C11—C12—N4 | −1.7 (3) |
C4—C5—C6—C1 | 0.6 (5) | C16—C11—C12—C13 | −1.6 (4) |
C2—C1—C6—C5 | −1.7 (4) | C9—C11—C12—C13 | 178.9 (2) |
C7—C1—C6—C5 | 176.1 (3) | N4—C12—C13—C14 | −178.6 (3) |
N3—N2—C7—O3 | −175.7 (2) | C11—C12—C13—C14 | 0.7 (4) |
N3—N2—C7—C1 | −0.1 (3) | C12—C13—C14—C15 | 0.5 (4) |
C6—C1—C7—O3 | 72.2 (3) | C13—C14—C15—C16 | −0.9 (4) |
C2—C1—C7—O3 | −110.3 (3) | C14—C15—C16—C11 | 0.0 (4) |
C6—C1—C7—N2 | −103.4 (3) | C12—C11—C16—C15 | 1.2 (4) |
C2—C1—C7—N2 | 74.1 (3) | C9—C11—C16—C15 | −179.5 (3) |
N2—N3—C8—C9 | −177.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2n···O3i | 0.86 | 2.11 | 2.961 (3) | 169 |
N4—H4n···O1ii | 0.86 | 2.35 | 3.087 (3) | 144 |
N4—H4n···O1wiii | 0.86 | 2.40 | 2.985 (3) | 126 |
O1w—H1w···O2 | 0.87 | 2.31 | 3.066 (3) | 146 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, −y, z−1/2; (iii) −x+1, −y, −z+1. |
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