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organic compounds
In the title compound, C16H12ClN3O, the amide O atom serves as an N—HO hydrogen-bond acceptor to the amide and amine groups of two adjacent molecules, resulting in a layered structure.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806037184/hb2146sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806037184/hb2146Isup2.hkl |
CCDC reference: 624618
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C)= 0.002 Å
- R factor = 0.037
- wR factor = 0.106
- Data-to-parameter ratio = 15.8
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
Computing details top
Data collection: APEXII (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.
5-Chloro-1H-indole-3-carbaldehyde benzoylhydrazone top
Crystal data top
C16H12ClN3O | F(000) = 616 |
Mr = 297.74 | Dx = 1.396 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3511 reflections |
a = 11.0860 (9) Å | θ = 2.5–25.7° |
b = 5.9337 (5) Å | µ = 0.27 mm−1 |
c = 21.625 (2) Å | T = 295 K |
β = 95.336 (1)° | Block, yellow |
V = 1416.3 (2) Å3 | 0.34 × 0.30 × 0.24 mm |
Z = 4 |
Data collection top
Bruker APEX-II CCD diffractometer | 2404 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 27.1°, θmin = 1.8° |
ω scans | h = −14→14 |
12576 measured reflections | k = −7→7 |
3131 independent reflections | l = −27→27 |
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)] = 0.037 | Hydrogen site location: difmap and geom |
wR(F2) = 0.106 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0525P)2 + 0.2701P] where P = (Fo2 + 2Fc2)/3 |
3131 reflections | (Δ/σ)max = 0.001 |
198 parameters | Δρmax = 0.20 e Å−3 |
2 restraints | Δρmin = −0.25 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.58021 (5) | 0.02346 (9) | 0.66464 (2) | 0.07121 (19) | |
O1 | 0.91244 (10) | 0.8269 (2) | 0.44111 (4) | 0.0502 (3) | |
N1 | 0.91379 (13) | 0.7961 (2) | 0.54393 (5) | 0.0443 (3) | |
N2 | 0.86470 (12) | 0.7135 (2) | 0.59648 (5) | 0.0412 (3) | |
N3 | 0.85821 (13) | 0.7094 (2) | 0.80865 (6) | 0.0451 (3) | |
C1 | 0.79003 (14) | 0.5325 (3) | 0.78332 (6) | 0.0395 (3) | |
C2 | 0.73001 (16) | 0.3617 (3) | 0.81168 (7) | 0.0501 (4) | |
H2 | 0.7326 | 0.3524 | 0.8547 | 0.060* | |
C3 | 0.66675 (16) | 0.2067 (3) | 0.77441 (8) | 0.0529 (4) | |
H3 | 0.6253 | 0.0907 | 0.7922 | 0.063* | |
C4 | 0.66437 (14) | 0.2225 (3) | 0.70995 (8) | 0.0464 (4) | |
C5 | 0.72548 (13) | 0.3873 (3) | 0.68071 (7) | 0.0410 (4) | |
H5 | 0.7239 | 0.3922 | 0.6377 | 0.049* | |
C6 | 0.78986 (13) | 0.5467 (3) | 0.71789 (6) | 0.0358 (3) | |
C7 | 0.86357 (13) | 0.7388 (3) | 0.70567 (6) | 0.0373 (3) | |
C8 | 0.90156 (14) | 0.8312 (3) | 0.76245 (7) | 0.0429 (4) | |
H8 | 0.9500 | 0.9588 | 0.7683 | 0.051* | |
C9 | 0.90033 (14) | 0.8142 (3) | 0.64702 (6) | 0.0400 (3) | |
H9 | 0.9510 | 0.9387 | 0.6459 | 0.048* | |
C10 | 0.87112 (14) | 0.7348 (3) | 0.48638 (6) | 0.0390 (3) | |
C11 | 0.77271 (13) | 0.5626 (3) | 0.47782 (6) | 0.0375 (3) | |
C12 | 0.77793 (15) | 0.3589 (3) | 0.50966 (7) | 0.0445 (4) | |
H12 | 0.8449 | 0.3249 | 0.5372 | 0.053* | |
C13 | 0.68363 (17) | 0.2071 (3) | 0.50032 (8) | 0.0533 (4) | |
H13 | 0.6874 | 0.0702 | 0.5214 | 0.064* | |
C14 | 0.58379 (16) | 0.2580 (3) | 0.45985 (8) | 0.0556 (5) | |
H14 | 0.5196 | 0.1567 | 0.4544 | 0.067* | |
C15 | 0.57861 (15) | 0.4580 (3) | 0.42737 (8) | 0.0537 (4) | |
H15 | 0.5115 | 0.4908 | 0.3998 | 0.064* | |
C16 | 0.67332 (14) | 0.6102 (3) | 0.43578 (7) | 0.0448 (4) | |
H16 | 0.6705 | 0.7441 | 0.4133 | 0.054* | |
H1N | 0.9691 (13) | 0.898 (3) | 0.5461 (9) | 0.062 (6)* | |
H3N | 0.8710 (18) | 0.735 (3) | 0.8480 (5) | 0.067 (6)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0706 (3) | 0.0680 (3) | 0.0728 (3) | −0.0299 (3) | −0.0049 (3) | 0.0029 (2) |
O1 | 0.0607 (7) | 0.0655 (8) | 0.0244 (5) | −0.0205 (6) | 0.0049 (5) | 0.0045 (5) |
N1 | 0.0519 (8) | 0.0562 (8) | 0.0247 (6) | −0.0209 (7) | 0.0034 (5) | 0.0048 (6) |
N2 | 0.0481 (7) | 0.0530 (8) | 0.0228 (6) | −0.0134 (6) | 0.0046 (5) | 0.0040 (5) |
N3 | 0.0550 (8) | 0.0588 (8) | 0.0215 (6) | 0.0022 (7) | 0.0035 (5) | −0.0007 (6) |
C1 | 0.0408 (8) | 0.0506 (9) | 0.0274 (7) | 0.0071 (7) | 0.0051 (6) | 0.0029 (6) |
C2 | 0.0572 (10) | 0.0619 (11) | 0.0336 (8) | 0.0051 (8) | 0.0164 (7) | 0.0125 (8) |
C3 | 0.0548 (10) | 0.0559 (10) | 0.0503 (10) | −0.0035 (8) | 0.0171 (8) | 0.0133 (8) |
C4 | 0.0421 (8) | 0.0510 (9) | 0.0460 (9) | −0.0052 (7) | 0.0042 (7) | 0.0034 (7) |
C5 | 0.0403 (8) | 0.0518 (9) | 0.0305 (7) | −0.0025 (7) | 0.0014 (6) | 0.0040 (7) |
C6 | 0.0353 (7) | 0.0463 (8) | 0.0259 (7) | 0.0027 (6) | 0.0036 (5) | 0.0048 (6) |
C7 | 0.0405 (8) | 0.0458 (8) | 0.0251 (7) | −0.0021 (7) | 0.0008 (6) | 0.0012 (6) |
C8 | 0.0471 (9) | 0.0498 (9) | 0.0314 (7) | −0.0031 (7) | 0.0024 (6) | −0.0017 (7) |
C9 | 0.0456 (8) | 0.0445 (8) | 0.0292 (7) | −0.0103 (7) | 0.0005 (6) | 0.0028 (6) |
C10 | 0.0442 (8) | 0.0481 (9) | 0.0249 (7) | −0.0057 (7) | 0.0032 (6) | 0.0020 (6) |
C11 | 0.0426 (8) | 0.0449 (8) | 0.0255 (7) | −0.0051 (7) | 0.0064 (6) | −0.0045 (6) |
C12 | 0.0508 (9) | 0.0473 (9) | 0.0355 (8) | −0.0030 (7) | 0.0044 (7) | −0.0011 (7) |
C13 | 0.0684 (11) | 0.0456 (9) | 0.0474 (9) | −0.0119 (8) | 0.0129 (8) | −0.0070 (8) |
C14 | 0.0538 (10) | 0.0647 (11) | 0.0499 (10) | −0.0204 (9) | 0.0140 (8) | −0.0191 (9) |
C15 | 0.0430 (9) | 0.0760 (12) | 0.0416 (9) | −0.0034 (8) | 0.0009 (7) | −0.0149 (9) |
C16 | 0.0493 (9) | 0.0527 (9) | 0.0322 (7) | −0.0018 (7) | 0.0030 (6) | −0.0046 (7) |
Geometric parameters (Å, º) top
Cl1—C4 | 1.7478 (17) | C6—C7 | 1.441 (2) |
O1—C10 | 1.2451 (17) | C7—C8 | 1.375 (2) |
N1—C10 | 1.3400 (18) | C7—C9 | 1.4393 (19) |
N1—N2 | 1.3938 (16) | C8—H8 | 0.9300 |
N1—H1N | 0.86 (1) | C9—H9 | 0.9300 |
N2—C9 | 1.2755 (19) | C10—C11 | 1.494 (2) |
N3—C8 | 1.357 (2) | C11—C12 | 1.389 (2) |
N3—C1 | 1.377 (2) | C11—C16 | 1.391 (2) |
N3—H3N | 0.86 (1) | C12—C13 | 1.381 (2) |
C1—C2 | 1.386 (2) | C12—H12 | 0.9300 |
C1—C6 | 1.4174 (19) | C13—C14 | 1.379 (3) |
C2—C3 | 1.372 (2) | C13—H13 | 0.9300 |
C2—H2 | 0.9300 | C14—C15 | 1.378 (3) |
C3—C4 | 1.395 (2) | C14—H14 | 0.9300 |
C3—H3 | 0.9300 | C15—C16 | 1.384 (2) |
C4—C5 | 1.377 (2) | C15—H15 | 0.9300 |
C5—C6 | 1.394 (2) | C16—H16 | 0.9300 |
C5—H5 | 0.9300 | ||
C10—N1—N2 | 122.06 (13) | N3—C8—C7 | 110.19 (15) |
C10—N1—H1N | 115.5 (13) | N3—C8—H8 | 124.9 |
N2—N1—H1N | 122.3 (13) | C7—C8—H8 | 124.9 |
C9—N2—N1 | 114.87 (13) | N2—C9—C7 | 121.27 (14) |
C8—N3—C1 | 109.39 (12) | N2—C9—H9 | 119.4 |
C8—N3—H3N | 126.6 (14) | C7—C9—H9 | 119.4 |
C1—N3—H3N | 124.0 (14) | O1—C10—N1 | 119.16 (14) |
N3—C1—C2 | 130.52 (14) | O1—C10—C11 | 121.38 (13) |
N3—C1—C6 | 107.55 (13) | N1—C10—C11 | 119.45 (12) |
C2—C1—C6 | 121.93 (15) | C12—C11—C16 | 119.64 (15) |
C3—C2—C1 | 118.07 (14) | C12—C11—C10 | 122.50 (14) |
C3—C2—H2 | 121.0 | C16—C11—C10 | 117.86 (14) |
C1—C2—H2 | 121.0 | C13—C12—C11 | 119.94 (16) |
C2—C3—C4 | 120.22 (15) | C13—C12—H12 | 120.0 |
C2—C3—H3 | 119.9 | C11—C12—H12 | 120.0 |
C4—C3—H3 | 119.9 | C12—C13—C14 | 120.13 (17) |
C5—C4—C3 | 122.84 (16) | C12—C13—H13 | 119.9 |
C5—C4—Cl1 | 118.84 (12) | C14—C13—H13 | 119.9 |
C3—C4—Cl1 | 118.32 (13) | C15—C14—C13 | 120.34 (16) |
C4—C5—C6 | 117.68 (13) | C15—C14—H14 | 119.8 |
C4—C5—H5 | 121.2 | C13—C14—H14 | 119.8 |
C6—C5—H5 | 121.2 | C14—C15—C16 | 120.00 (17) |
C5—C6—C1 | 119.24 (13) | C14—C15—H15 | 120.0 |
C5—C6—C7 | 134.38 (13) | C16—C15—H15 | 120.0 |
C1—C6—C7 | 106.37 (13) | C15—C16—C11 | 119.91 (16) |
C8—C7—C9 | 125.08 (15) | C15—C16—H16 | 120.0 |
C8—C7—C6 | 106.48 (12) | C11—C16—H16 | 120.0 |
C9—C7—C6 | 128.27 (13) | ||
C10—N1—N2—C9 | −168.78 (15) | C1—N3—C8—C7 | −0.04 (19) |
C8—N3—C1—C2 | 178.61 (16) | C9—C7—C8—N3 | −174.89 (14) |
C8—N3—C1—C6 | −0.70 (18) | C6—C7—C8—N3 | 0.76 (18) |
N3—C1—C2—C3 | 179.20 (16) | N1—N2—C9—C7 | −176.01 (14) |
C6—C1—C2—C3 | −1.6 (2) | C8—C7—C9—N2 | 177.16 (16) |
C1—C2—C3—C4 | 0.3 (3) | C6—C7—C9—N2 | 2.5 (3) |
C2—C3—C4—C5 | 1.2 (3) | N2—N1—C10—O1 | 174.63 (14) |
C2—C3—C4—Cl1 | −178.90 (13) | N2—N1—C10—C11 | −3.6 (2) |
C3—C4—C5—C6 | −1.4 (2) | O1—C10—C11—C12 | 132.90 (16) |
Cl1—C4—C5—C6 | 178.69 (12) | N1—C10—C11—C12 | −48.9 (2) |
C4—C5—C6—C1 | 0.2 (2) | O1—C10—C11—C16 | −46.5 (2) |
C4—C5—C6—C7 | 179.62 (16) | N1—C10—C11—C16 | 131.69 (16) |
N3—C1—C6—C5 | −179.26 (13) | C16—C11—C12—C13 | −1.2 (2) |
C2—C1—C6—C5 | 1.4 (2) | C10—C11—C12—C13 | 179.35 (14) |
N3—C1—C6—C7 | 1.14 (16) | C11—C12—C13—C14 | −0.6 (2) |
C2—C1—C6—C7 | −178.25 (14) | C12—C13—C14—C15 | 1.5 (3) |
C5—C6—C7—C8 | 179.33 (17) | C13—C14—C15—C16 | −0.7 (3) |
C1—C6—C7—C8 | −1.15 (17) | C14—C15—C16—C11 | −1.1 (2) |
C5—C6—C7—C9 | −5.2 (3) | C12—C11—C16—C15 | 2.1 (2) |
C1—C6—C7—C9 | 174.30 (15) | C10—C11—C16—C15 | −178.50 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.86 (1) | 2.10 (1) | 2.950 (2) | 172 (2) |
N3—H3N···O1ii | 0.86 (1) | 2.06 (1) | 2.880 (2) | 159 (2) |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) x, −y+3/2, z+1/2. |
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