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In the title compound, C16H12ClN3O, the amide O atom serves as an N—H...O hydrogen-bond acceptor to the amide and amine groups of two adjacent mol­ecules, resulting in a layered structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806037184/hb2146sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806037184/hb2146Isup2.hkl
Contains datablock I

CCDC reference: 624618

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](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
C16H12ClN3OF(000) = 616
Mr = 297.74Dx = 1.396 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3511 reflections
a = 11.0860 (9) Åθ = 2.5–25.7°
b = 5.9337 (5) ŵ = 0.27 mm1
c = 21.625 (2) ÅT = 295 K
β = 95.336 (1)°Block, yellow
V = 1416.3 (2) Å30.34 × 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 tubeRint = 0.023
Graphite monochromatorθmax = 27.1°, θmin = 1.8°
ω scansh = 1414
12576 measured reflectionsk = 77
3131 independent reflectionsl = 2727
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: difmap and geom
wR(F2) = 0.106H 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 parametersΔρmax = 0.20 e Å3
2 restraintsΔρmin = 0.25 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.58021 (5)0.02346 (9)0.66464 (2)0.07121 (19)
O10.91244 (10)0.8269 (2)0.44111 (4)0.0502 (3)
N10.91379 (13)0.7961 (2)0.54393 (5)0.0443 (3)
N20.86470 (12)0.7135 (2)0.59648 (5)0.0412 (3)
N30.85821 (13)0.7094 (2)0.80865 (6)0.0451 (3)
C10.79003 (14)0.5325 (3)0.78332 (6)0.0395 (3)
C20.73001 (16)0.3617 (3)0.81168 (7)0.0501 (4)
H20.73260.35240.85470.060*
C30.66675 (16)0.2067 (3)0.77441 (8)0.0529 (4)
H30.62530.09070.79220.063*
C40.66437 (14)0.2225 (3)0.70995 (8)0.0464 (4)
C50.72548 (13)0.3873 (3)0.68071 (7)0.0410 (4)
H50.72390.39220.63770.049*
C60.78986 (13)0.5467 (3)0.71789 (6)0.0358 (3)
C70.86357 (13)0.7388 (3)0.70567 (6)0.0373 (3)
C80.90156 (14)0.8312 (3)0.76245 (7)0.0429 (4)
H80.95000.95880.76830.051*
C90.90033 (14)0.8142 (3)0.64702 (6)0.0400 (3)
H90.95100.93870.64590.048*
C100.87112 (14)0.7348 (3)0.48638 (6)0.0390 (3)
C110.77271 (13)0.5626 (3)0.47782 (6)0.0375 (3)
C120.77793 (15)0.3589 (3)0.50966 (7)0.0445 (4)
H120.84490.32490.53720.053*
C130.68363 (17)0.2071 (3)0.50032 (8)0.0533 (4)
H130.68740.07020.52140.064*
C140.58379 (16)0.2580 (3)0.45985 (8)0.0556 (5)
H140.51960.15670.45440.067*
C150.57861 (15)0.4580 (3)0.42737 (8)0.0537 (4)
H150.51150.49080.39980.064*
C160.67332 (14)0.6102 (3)0.43578 (7)0.0448 (4)
H160.67050.74410.41330.054*
H1N0.9691 (13)0.898 (3)0.5461 (9)0.062 (6)*
H3N0.8710 (18)0.735 (3)0.8480 (5)0.067 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0706 (3)0.0680 (3)0.0728 (3)0.0299 (3)0.0049 (3)0.0029 (2)
O10.0607 (7)0.0655 (8)0.0244 (5)0.0205 (6)0.0049 (5)0.0045 (5)
N10.0519 (8)0.0562 (8)0.0247 (6)0.0209 (7)0.0034 (5)0.0048 (6)
N20.0481 (7)0.0530 (8)0.0228 (6)0.0134 (6)0.0046 (5)0.0040 (5)
N30.0550 (8)0.0588 (8)0.0215 (6)0.0022 (7)0.0035 (5)0.0007 (6)
C10.0408 (8)0.0506 (9)0.0274 (7)0.0071 (7)0.0051 (6)0.0029 (6)
C20.0572 (10)0.0619 (11)0.0336 (8)0.0051 (8)0.0164 (7)0.0125 (8)
C30.0548 (10)0.0559 (10)0.0503 (10)0.0035 (8)0.0171 (8)0.0133 (8)
C40.0421 (8)0.0510 (9)0.0460 (9)0.0052 (7)0.0042 (7)0.0034 (7)
C50.0403 (8)0.0518 (9)0.0305 (7)0.0025 (7)0.0014 (6)0.0040 (7)
C60.0353 (7)0.0463 (8)0.0259 (7)0.0027 (6)0.0036 (5)0.0048 (6)
C70.0405 (8)0.0458 (8)0.0251 (7)0.0021 (7)0.0008 (6)0.0012 (6)
C80.0471 (9)0.0498 (9)0.0314 (7)0.0031 (7)0.0024 (6)0.0017 (7)
C90.0456 (8)0.0445 (8)0.0292 (7)0.0103 (7)0.0005 (6)0.0028 (6)
C100.0442 (8)0.0481 (9)0.0249 (7)0.0057 (7)0.0032 (6)0.0020 (6)
C110.0426 (8)0.0449 (8)0.0255 (7)0.0051 (7)0.0064 (6)0.0045 (6)
C120.0508 (9)0.0473 (9)0.0355 (8)0.0030 (7)0.0044 (7)0.0011 (7)
C130.0684 (11)0.0456 (9)0.0474 (9)0.0119 (8)0.0129 (8)0.0070 (8)
C140.0538 (10)0.0647 (11)0.0499 (10)0.0204 (9)0.0140 (8)0.0191 (9)
C150.0430 (9)0.0760 (12)0.0416 (9)0.0034 (8)0.0009 (7)0.0149 (9)
C160.0493 (9)0.0527 (9)0.0322 (7)0.0018 (7)0.0030 (6)0.0046 (7)
Geometric parameters (Å, º) top
Cl1—C41.7478 (17)C6—C71.441 (2)
O1—C101.2451 (17)C7—C81.375 (2)
N1—C101.3400 (18)C7—C91.4393 (19)
N1—N21.3938 (16)C8—H80.9300
N1—H1N0.86 (1)C9—H90.9300
N2—C91.2755 (19)C10—C111.494 (2)
N3—C81.357 (2)C11—C121.389 (2)
N3—C11.377 (2)C11—C161.391 (2)
N3—H3N0.86 (1)C12—C131.381 (2)
C1—C21.386 (2)C12—H120.9300
C1—C61.4174 (19)C13—C141.379 (3)
C2—C31.372 (2)C13—H130.9300
C2—H20.9300C14—C151.378 (3)
C3—C41.395 (2)C14—H140.9300
C3—H30.9300C15—C161.384 (2)
C4—C51.377 (2)C15—H150.9300
C5—C61.394 (2)C16—H160.9300
C5—H50.9300
C10—N1—N2122.06 (13)N3—C8—C7110.19 (15)
C10—N1—H1N115.5 (13)N3—C8—H8124.9
N2—N1—H1N122.3 (13)C7—C8—H8124.9
C9—N2—N1114.87 (13)N2—C9—C7121.27 (14)
C8—N3—C1109.39 (12)N2—C9—H9119.4
C8—N3—H3N126.6 (14)C7—C9—H9119.4
C1—N3—H3N124.0 (14)O1—C10—N1119.16 (14)
N3—C1—C2130.52 (14)O1—C10—C11121.38 (13)
N3—C1—C6107.55 (13)N1—C10—C11119.45 (12)
C2—C1—C6121.93 (15)C12—C11—C16119.64 (15)
C3—C2—C1118.07 (14)C12—C11—C10122.50 (14)
C3—C2—H2121.0C16—C11—C10117.86 (14)
C1—C2—H2121.0C13—C12—C11119.94 (16)
C2—C3—C4120.22 (15)C13—C12—H12120.0
C2—C3—H3119.9C11—C12—H12120.0
C4—C3—H3119.9C12—C13—C14120.13 (17)
C5—C4—C3122.84 (16)C12—C13—H13119.9
C5—C4—Cl1118.84 (12)C14—C13—H13119.9
C3—C4—Cl1118.32 (13)C15—C14—C13120.34 (16)
C4—C5—C6117.68 (13)C15—C14—H14119.8
C4—C5—H5121.2C13—C14—H14119.8
C6—C5—H5121.2C14—C15—C16120.00 (17)
C5—C6—C1119.24 (13)C14—C15—H15120.0
C5—C6—C7134.38 (13)C16—C15—H15120.0
C1—C6—C7106.37 (13)C15—C16—C11119.91 (16)
C8—C7—C9125.08 (15)C15—C16—H16120.0
C8—C7—C6106.48 (12)C11—C16—H16120.0
C9—C7—C6128.27 (13)
C10—N1—N2—C9168.78 (15)C1—N3—C8—C70.04 (19)
C8—N3—C1—C2178.61 (16)C9—C7—C8—N3174.89 (14)
C8—N3—C1—C60.70 (18)C6—C7—C8—N30.76 (18)
N3—C1—C2—C3179.20 (16)N1—N2—C9—C7176.01 (14)
C6—C1—C2—C31.6 (2)C8—C7—C9—N2177.16 (16)
C1—C2—C3—C40.3 (3)C6—C7—C9—N22.5 (3)
C2—C3—C4—C51.2 (3)N2—N1—C10—O1174.63 (14)
C2—C3—C4—Cl1178.90 (13)N2—N1—C10—C113.6 (2)
C3—C4—C5—C61.4 (2)O1—C10—C11—C12132.90 (16)
Cl1—C4—C5—C6178.69 (12)N1—C10—C11—C1248.9 (2)
C4—C5—C6—C10.2 (2)O1—C10—C11—C1646.5 (2)
C4—C5—C6—C7179.62 (16)N1—C10—C11—C16131.69 (16)
N3—C1—C6—C5179.26 (13)C16—C11—C12—C131.2 (2)
C2—C1—C6—C51.4 (2)C10—C11—C12—C13179.35 (14)
N3—C1—C6—C71.14 (16)C11—C12—C13—C140.6 (2)
C2—C1—C6—C7178.25 (14)C12—C13—C14—C151.5 (3)
C5—C6—C7—C8179.33 (17)C13—C14—C15—C160.7 (3)
C1—C6—C7—C81.15 (17)C14—C15—C16—C111.1 (2)
C5—C6—C7—C95.2 (3)C12—C11—C16—C152.1 (2)
C1—C6—C7—C9174.30 (15)C10—C11—C16—C15178.50 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.86 (1)2.10 (1)2.950 (2)172 (2)
N3—H3N···O1ii0.86 (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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