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Mol­ecules of 5-bromo-1H-indole-3-carbaldehyde 3-methoxy­benzoyl­ylhydrazone, C17H14BrN3O2, are paired by amino-carbon­yl hydrogen bonds over a center of inversion, and adjacent pairs are further linked by hydrogen bonds into ribbons.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805020787/sj6112sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805020787/sj6112Isup2.hkl
Contains datablock I

CCDC reference: 282633

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.042
  • wR factor = 0.114
  • Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.75 PLAT411_ALERT_2_B Short Inter H...H Contact H11 .. H11 .. 2.03 Ang.
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.315 0.650 Tmin(prime) and Tmax expected: 0.392 0.624 RR(prime) = 0.772 Please check that your absorption correction is appropriate. PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); 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.

5-Bromo-1H-indole-3-carbaldehyde 3-methoxybenzoylhydrazone top
Crystal data top
C17H14BrN3O2F(000) = 1504
Mr = 372.22Dx = 1.566 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9770 reflections
a = 19.257 (4) Åθ = 3.1–27.5°
b = 8.904 (3) ŵ = 2.62 mm1
c = 19.400 (4) ÅT = 295 K
β = 108.330 (17)°Block, brown
V = 3157.7 (13) Å30.35 × 0.24 × 0.18 mm
Z = 8
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3616 independent reflections
Radiation source: fine-focus sealed tube2664 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
Detector resolution: 10 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 2423
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1111
Tmin = 0.315, Tmax = 0.650l = 2525
15076 measured reflections
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0492P)2 + 3.744P]
where P = (Fo2 + 2Fc2)/3
3616 reflections(Δ/σ)max = 0.001
216 parametersΔρmax = 0.49 e Å3
2 restraintsΔρmin = 0.75 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.11452 (2)0.45712 (4)0.31863 (2)0.0762 (2)
O10.3015 (1)0.3651 (2)0.3544 (1)0.056 (1)
O20.5180 (1)0.8291 (2)0.4557 (1)0.048 (1)
N10.4080 (1)0.9026 (3)0.4576 (1)0.040 (1)
N20.3324 (1)0.8879 (2)0.4355 (1)0.034 (1)
N30.1095 (1)1.0703 (3)0.4399 (1)0.048 (1)
C10.3697 (1)0.5850 (3)0.3892 (1)0.034 (1)
C20.3447 (1)0.4716 (3)0.3383 (1)0.037 (1)
C30.3642 (2)0.4721 (3)0.2752 (1)0.042 (1)
C40.4111 (2)0.5813 (3)0.2656 (1)0.043 (1)
C50.4388 (1)0.6896 (3)0.3171 (1)0.038 (1)
C60.4169 (1)0.6923 (3)0.3791 (1)0.031 (1)
C70.2739 (2)0.2488 (4)0.3035 (2)0.072 (1)
C80.4509 (1)0.8117 (3)0.4339 (1)0.034 (1)
C90.2997 (1)0.9876 (3)0.4605 (2)0.045 (1)
C100.2211 (1)0.9876 (3)0.4452 (2)0.040 (1)
C110.1817 (2)1.1039 (4)0.4603 (2)0.056 (1)
C120.1694 (1)0.8729 (3)0.4136 (1)0.032 (1)
C130.1740 (1)0.7294 (3)0.3866 (1)0.036 (1)
C140.1107 (2)0.6500 (3)0.3594 (2)0.044 (1)
C150.0423 (2)0.7042 (4)0.3590 (2)0.051 (1)
C160.0368 (2)0.8437 (3)0.3858 (2)0.046 (1)
C170.1001 (1)0.9280 (3)0.4122 (1)0.035 (1)
H1n0.429 (1)0.974 (3)0.487 (1)0.039 (7)*
H3n0.079 (2)1.136 (3)0.446 (2)0.056 (9)*
H10.35450.58830.43020.041*
H30.34580.39930.23980.050*
H40.42410.58140.22330.051*
H50.47180.76030.31080.045*
H7a0.24450.18200.32150.108*
H7b0.31390.19400.29610.108*
H7c0.24460.29130.25820.108*
H90.32721.06320.48970.054*
H110.20181.19400.48160.067*
H120.21880.68920.38700.043*
H140.00070.64530.34030.061*
H150.00810.88110.38640.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0598 (2)0.0475 (2)0.1200 (4)0.0120 (2)0.0264 (2)0.0331 (2)
O10.062 (1)0.047 (1)0.064 (1)0.023 (1)0.028 (1)0.015 (1)
O20.028 (1)0.047 (1)0.068 (1)0.000 (1)0.014 (1)0.023 (1)
N10.027 (1)0.037 (1)0.056 (1)0.000 (1)0.011 (1)0.019 (1)
N20.024 (1)0.033 (1)0.046 (1)0.002 (1)0.009 (1)0.009 (1)
N30.031 (1)0.044 (1)0.068 (2)0.011 (1)0.015 (1)0.012 (1)
C10.029 (1)0.037 (1)0.037 (1)0.000 (1)0.012 (1)0.007 (1)
C20.032 (1)0.032 (1)0.045 (1)0.000 (1)0.012 (1)0.004 (1)
C30.044 (2)0.040 (2)0.039 (1)0.001 (1)0.010 (1)0.011 (1)
C40.047 (2)0.049 (2)0.036 (1)0.002 (1)0.017 (1)0.005 (1)
C50.035 (1)0.036 (1)0.043 (1)0.000 (1)0.016 (1)0.002 (1)
C60.025 (1)0.031 (1)0.037 (1)0.006 (1)0.008 (1)0.004 (1)
C70.073 (2)0.050 (2)0.091 (2)0.027 (2)0.024 (2)0.023 (2)
C80.0259 (1)0.033 (1)0.043 (1)0.002 (1)0.011 (1)0.006 (1)
C90.0309 (1)0.036 (1)0.066 (2)0.001 (1)0.012 (1)0.018 (1)
C100.028 (1)0.038 (1)0.054 (2)0.006 (1)0.011 (1)0.011 (1)
C110.035 (2)0.041 (2)0.091 (2)0.003 (1)0.016 (2)0.026 (2)
C120.030 (1)0.035 (1)0.032 (1)0.005 (1)0.010 (1)0.003 (1)
C130.033 (1)0.033 (1)0.041 (1)0.004 (1)0.013 (1)0.001 (1)
C140.040 (2)0.035 (1)0.054 (2)0.000 (1)0.011 (1)0.003 (1)
C150.034 (2)0.050 (2)0.065 (2)0.005 (1)0.011 (1)0.000 (1)
C160.030 (1)0.051 (2)0.057 (2)0.006 (1)0.012 (1)0.004 (1)
C170.030 (1)0.039 (1)0.037 (1)0.007 (1)0.010 (1)0.002 (1)
Geometric parameters (Å, º) top
Br1—C141.902 (3)C12—C171.414 (3)
O1—C21.362 (3)C13—C141.364 (4)
O1—C71.415 (4)C14—C151.400 (4)
O2—C81.236 (3)C15—C161.364 (4)
N1—C81.336 (3)C16—C171.385 (4)
N1—N21.388 (3)N1—H1n0.87 (2)
N2—C91.270 (3)N3—H3n0.85 (2)
N3—C111.354 (4)C1—H10.93
N3—C171.366 (3)C3—H30.93
C1—C61.374 (3)C4—H40.93
C1—C21.389 (3)C5—H50.93
C2—C31.388 (4)C7—H7a0.96
C3—C41.379 (4)C7—H7b0.96
C4—C51.371 (4)C7—H7c0.96
C5—C61.395 (3)C9—H90.93
C6—C81.501 (3)C11—H110.93
C9—C101.448 (4)C13—H120.93
C10—C111.369 (4)C15—H140.93
C10—C121.423 (4)C16—H150.93
C12—C131.395 (3)
C2—O1—C7118.1 (2)N3—C17—C16129.8 (2)
C8—N1—N2122.6 (2)N3—C17—C12107.8 (2)
C9—N2—N1114.4 (2)C16—C17—C12122.4 (2)
C11—N3—C17108.4 (2)C8—N1—H1n117 (2)
C6—C1—C2120.1 (2)N2—N1—H1n120 (2)
O1—C2—C3124.0 (2)C11—N3—H3n119 (2)
O1—C2—C1116.3 (2)C17—N3—H3n132 (2)
C3—C2—C1119.7 (2)C6—C1—H1120.0
C4—C3—C2119.5 (2)C2—C1—H1120.0
C5—C4—C3121.2 (2)C4—C3—H3120.3
C4—C5—C6119.1 (2)C2—C3—H3120.3
C1—C6—C5120.3 (2)C5—C4—H4119.4
C1—C6—C8123.5 (2)C3—C4—H4119.4
C5—C6—C8116.1 (2)C4—C5—H5120.4
O2—C8—N1119.9 (2)C6—C5—H5120.4
O2—C8—C6120.5 (2)O1—C7—H7a109.5
N1—C8—C6119.6 (2)O1—C7—H7b109.5
N2—C9—C10122.2 (3)H7a—C7—H7b109.5
C11—C10—C12105.9 (2)O1—C7—H7c109.5
C11—C10—C9124.8 (3)H7a—C7—H7c109.5
C12—C10—C9129.3 (2)H7b—C7—H7c109.5
N3—C11—C10111.0 (3)N2—C9—H9118.9
C13—C12—C17118.8 (2)C10—C9—H9118.9
C13—C12—C10134.4 (2)N3—C11—H11124.5
C17—C12—C10106.8 (2)C10—C11—H11124.5
C14—C13—C12117.7 (2)C14—C13—H12121.1
C13—C14—C15123.3 (3)C12—C13—H12121.1
C13—C14—Br1118.8 (2)C16—C15—H14120.1
C15—C14—Br1117.9 (2)C14—C15—H14120.1
C16—C15—C14119.9 (3)C15—C16—H15121.0
C15—C16—C17118.0 (3)C17—C16—H15121.0
C8—N1—N2—C9176.9 (3)C17—N3—C11—C101.4 (4)
C7—O1—C2—C30.8 (4)C12—C10—C11—N30.5 (4)
C7—O1—C2—C1179.1 (3)C9—C10—C11—N3179.8 (3)
C6—C1—C2—O1176.5 (2)C11—C10—C12—C13179.6 (3)
C6—C1—C2—C33.7 (4)C9—C10—C12—C131.1 (5)
O1—C2—C3—C4177.0 (3)C11—C10—C12—C170.6 (3)
C1—C2—C3—C43.1 (4)C9—C10—C12—C17178.7 (3)
C2—C3—C4—C50.0 (4)C17—C12—C13—C140.5 (3)
C3—C4—C5—C62.5 (4)C10—C12—C13—C14179.7 (3)
C2—C1—C6—C51.2 (4)C12—C13—C14—C151.4 (4)
C2—C1—C6—C8175.3 (2)C12—C13—C14—Br1177.56 (18)
C4—C5—C6—C11.9 (4)C13—C14—C15—C160.8 (5)
C4—C5—C6—C8178.6 (2)Br1—C14—C15—C16178.2 (2)
N2—N1—C8—O2179.5 (2)C14—C15—C16—C170.7 (4)
N2—N1—C8—C62.5 (4)C11—N3—C17—C16178.6 (3)
C1—C6—C8—O2126.2 (3)C11—N3—C17—C121.7 (3)
C5—C6—C8—O250.3 (3)C15—C16—C17—N3178.1 (3)
C1—C6—C8—N155.8 (4)C15—C16—C17—C121.6 (4)
C5—C6—C8—N1127.6 (3)C13—C12—C17—N3178.8 (2)
N1—N2—C9—C10178.0 (3)C10—C12—C17—N31.4 (3)
N2—C9—C10—C11168.6 (3)C13—C12—C17—C161.0 (4)
N2—C9—C10—C1212.3 (5)C10—C12—C17—C16178.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n···O2i0.87 (2)2.15 (2)3.010 (3)170 (3)
N3—H3n···O2ii0.85 (2)2.13 (2)2.976 (3)169 (3)
Symmetry codes: (i) x+1, y+2, z+1; (ii) x1/2, y+1/2, z.
 

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