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The mol­ecules of the title compound, C19H15ClN4O, are linked into a three-dimensional architecture by N—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680701135X/hb2318sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680701135X/hb2318Isup2.hkl
Contains datablock I

CCDC reference: 643011

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.026
  • wR factor = 0.084
  • Data-to-parameter ratio = 8.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro . ? PLAT420_ALERT_2_C D-H Without Acceptor N4 - H4N ... ? PLAT432_ALERT_2_C Short Inter X...Y Contact Cl1 .. C5 .. 3.21 Ang. PLAT731_ALERT_1_C Bond Calc 0.88(3), Rep 0.877(10) ...... 3.00 su-Ra N1 -H1N 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.88(3), Rep 0.878(10) ...... 3.00 su-Ra N4 -H4N 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.88(3), Rep 0.880(10) ...... 3.00 su-Ra N1 -H1N 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 2.02(3), Rep 2.020(10) ...... 3.00 su-Ra H1N -O1 1.555 3.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C19 H15 Cl N4 O
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 1928 Count of symmetry unique reflns 1931 Completeness (_total/calc) 99.84% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (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: publCIF (Westrip, 2007).

2'-[(5-Chloro-1H-indol-3-yl)methylene]-2-(1H-indol-3-yl)acetohydrazide top
Crystal data top
C19H15ClN4OF(000) = 728
Mr = 350.80Dx = 1.392 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 6161 reflections
a = 13.7442 (2) Åθ = 2.7–33.9°
b = 15.0424 (2) ŵ = 0.24 mm1
c = 8.3120 (1) ÅT = 173 K
β = 103.095 (1)°Block, yellow
V = 1673.78 (4) Å30.47 × 0.32 × 0.30 mm
Z = 4
Data collection top
Bruker APEX II CCD
diffractometer
1892 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tubeRint = 0.059
Graphite monochromatorθmax = 27.5°, θmin = 2.0°
ω scansh = 1717
12652 measured reflectionsk = 1919
1928 independent reflectionsl = 1010
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)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H atoms treated by a mixture of independent and constrained refinement
S = 1.15 w = 1/[σ2(Fo2) + (0.0568P)2 + 0.0652P]
where P = (Fo2 + 2Fc2)/3
1928 reflections(Δ/σ)max = 0.001
238 parametersΔρmax = 0.24 e Å3
5 restraintsΔρmin = 0.22 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.50000 (4)0.55864 (3)0.50000 (6)0.02693 (15)
O10.16270 (11)0.41738 (10)0.11024 (17)0.0199 (3)
N10.52187 (14)0.78206 (12)0.0642 (2)0.0235 (4)
N20.28012 (13)0.55948 (10)0.1611 (2)0.0162 (3)
N30.21514 (12)0.51299 (11)0.2862 (2)0.0164 (3)
N40.14405 (17)0.52291 (18)0.4071 (3)0.0405 (6)
C10.53003 (15)0.73493 (14)0.0803 (3)0.0210 (4)
C20.60075 (16)0.74165 (15)0.2289 (3)0.0246 (4)
H20.65320.78410.24300.029*
C30.59228 (16)0.68441 (14)0.3556 (3)0.0237 (4)
H30.64020.68620.45780.028*
C40.51301 (15)0.62402 (13)0.3327 (3)0.0197 (4)
C50.44329 (14)0.61484 (12)0.1845 (2)0.0176 (4)
H50.39070.57270.17210.021*
C60.45334 (14)0.66997 (12)0.0539 (2)0.0171 (4)
C70.40108 (15)0.67811 (13)0.1164 (2)0.0187 (4)
C80.44595 (17)0.74773 (13)0.1811 (3)0.0231 (4)
H80.42630.76850.29160.028*
C90.32516 (13)0.62370 (12)0.2184 (2)0.0174 (4)
H90.30720.63560.33360.021*
C100.16111 (14)0.44461 (12)0.2519 (3)0.0152 (4)
C110.09218 (14)0.40324 (13)0.4026 (2)0.0173 (4)
H11A0.11730.41720.50230.021*
H11B0.09220.33780.38970.021*
C120.01274 (16)0.43775 (13)0.4244 (3)0.0191 (4)
C130.04244 (18)0.51355 (17)0.3589 (3)0.0318 (5)
H130.00110.55400.28980.038*
C140.18285 (18)0.45144 (17)0.5027 (3)0.0286 (5)
C150.28168 (19)0.4297 (2)0.5789 (3)0.0372 (6)
H150.33560.46690.56780.045*
C160.29792 (17)0.3530 (2)0.6701 (3)0.0357 (6)
H160.36440.33660.72150.043*
C170.21891 (18)0.29820 (16)0.6895 (3)0.0324 (5)
H170.23270.24590.75480.039*
C180.12079 (16)0.31930 (14)0.6146 (3)0.0233 (4)
H180.06740.28210.62810.028*
C190.10217 (14)0.39664 (14)0.5186 (2)0.0188 (4)
H1N0.5651 (19)0.8209 (16)0.085 (4)0.034 (8)*
H3N0.205 (3)0.531 (3)0.389 (2)0.046 (9)*
H4N0.179 (2)0.5663 (17)0.377 (5)0.046 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0305 (3)0.0286 (3)0.0199 (2)0.0051 (2)0.00189 (18)0.00593 (19)
O10.0227 (7)0.0206 (7)0.0154 (7)0.0064 (6)0.0025 (5)0.0008 (6)
N10.0281 (9)0.0202 (8)0.0226 (9)0.0103 (7)0.0066 (7)0.0010 (7)
N20.0148 (7)0.0172 (8)0.0150 (8)0.0019 (5)0.0002 (6)0.0015 (6)
N30.0180 (7)0.0187 (8)0.0113 (7)0.0031 (6)0.0004 (6)0.0008 (6)
N40.0297 (11)0.0486 (14)0.0389 (13)0.0165 (9)0.0010 (9)0.0188 (10)
C10.0224 (10)0.0188 (9)0.0229 (10)0.0051 (7)0.0070 (8)0.0012 (8)
C20.0237 (10)0.0239 (10)0.0254 (10)0.0102 (8)0.0038 (8)0.0043 (8)
C30.0218 (10)0.0260 (10)0.0213 (10)0.0041 (8)0.0010 (8)0.0029 (8)
C40.0235 (10)0.0181 (9)0.0175 (9)0.0007 (7)0.0050 (7)0.0009 (7)
C50.0183 (9)0.0138 (8)0.0207 (9)0.0023 (6)0.0042 (7)0.0016 (7)
C60.0159 (8)0.0153 (8)0.0202 (9)0.0013 (6)0.0042 (7)0.0024 (7)
C70.0192 (9)0.0172 (8)0.0197 (10)0.0028 (7)0.0042 (7)0.0011 (7)
C80.0255 (10)0.0219 (10)0.0214 (10)0.0041 (8)0.0042 (8)0.0023 (8)
C90.0165 (9)0.0181 (9)0.0169 (9)0.0002 (7)0.0022 (7)0.0018 (7)
C100.0136 (8)0.0156 (8)0.0158 (9)0.0006 (6)0.0020 (7)0.0020 (6)
C110.0171 (9)0.0180 (9)0.0156 (8)0.0027 (7)0.0012 (7)0.0035 (7)
C120.0183 (10)0.0218 (9)0.0158 (10)0.0011 (7)0.0008 (8)0.0001 (7)
C130.0288 (12)0.0332 (12)0.0291 (11)0.0060 (9)0.0021 (9)0.0124 (9)
C140.0231 (11)0.0376 (12)0.0239 (12)0.0047 (9)0.0027 (9)0.0022 (9)
C150.0179 (11)0.0584 (17)0.0331 (14)0.0090 (10)0.0010 (10)0.0016 (12)
C160.0177 (10)0.0506 (15)0.0341 (13)0.0078 (9)0.0039 (9)0.0097 (11)
C170.0290 (12)0.0269 (11)0.0347 (13)0.0107 (9)0.0064 (9)0.0034 (9)
C180.0209 (9)0.0206 (9)0.0257 (11)0.0028 (7)0.0005 (8)0.0026 (8)
C190.0171 (8)0.0226 (9)0.0156 (8)0.0013 (7)0.0017 (7)0.0038 (7)
Geometric parameters (Å, º) top
Cl1—C41.746 (2)C7—C81.384 (3)
O1—C101.242 (3)C7—C91.441 (3)
N1—C81.356 (3)C8—H80.9500
N1—C11.377 (3)C9—H90.9500
N1—H1N0.877 (10)C10—C111.522 (3)
N2—C91.295 (2)C11—C121.504 (3)
N2—N31.395 (2)C11—H11A0.9900
N3—C101.337 (2)C11—H11B0.9900
N3—H3N0.879 (10)C12—C131.365 (3)
N4—C131.370 (3)C12—C191.439 (3)
N4—C141.371 (4)C13—H130.9500
N4—H4N0.878 (10)C14—C151.401 (4)
C1—C21.392 (3)C14—C191.412 (3)
C1—C61.417 (3)C15—C161.370 (4)
C2—C31.385 (3)C15—H150.9500
C2—H20.9500C16—C171.401 (4)
C3—C41.398 (3)C16—H160.9500
C3—H30.9500C17—C181.388 (3)
C4—C51.385 (3)C17—H170.9500
C5—C61.397 (3)C18—C191.401 (3)
C5—H50.9500C18—H180.9500
C6—C71.441 (3)
C8—N1—C1109.02 (17)N2—C9—H9118.3
C8—N1—H1N124 (2)C7—C9—H9118.3
C1—N1—H1N126 (2)O1—C10—N3124.39 (18)
C9—N2—N3112.24 (17)O1—C10—C11121.30 (17)
C10—N3—N2121.27 (17)N3—C10—C11114.27 (17)
C10—N3—H3N118 (3)C12—C11—C10111.04 (16)
N2—N3—H3N120 (3)C12—C11—H11A109.4
C13—N4—C14109.0 (2)C10—C11—H11A109.4
C13—N4—H4N125 (3)C12—C11—H11B109.4
C14—N4—H4N126 (3)C10—C11—H11B109.4
N1—C1—C2129.72 (19)H11A—C11—H11B108.0
N1—C1—C6108.02 (18)C13—C12—C19106.27 (19)
C2—C1—C6122.2 (2)C13—C12—C11127.24 (19)
C3—C2—C1117.86 (19)C19—C12—C11126.48 (17)
C3—C2—H2121.1C12—C13—N4110.3 (2)
C1—C2—H2121.1C12—C13—H13124.9
C2—C3—C4119.8 (2)N4—C13—H13124.9
C2—C3—H3120.1N4—C14—C15130.9 (2)
C4—C3—H3120.1N4—C14—C19107.5 (2)
C5—C4—C3123.14 (19)C15—C14—C19121.5 (2)
C5—C4—Cl1118.50 (15)C16—C15—C14117.8 (2)
C3—C4—Cl1118.35 (16)C16—C15—H15121.1
C4—C5—C6117.45 (17)C14—C15—H15121.1
C4—C5—H5121.3C15—C16—C17121.7 (2)
C6—C5—H5121.3C15—C16—H16119.2
C5—C6—C1119.34 (18)C17—C16—H16119.2
C5—C6—C7134.34 (17)C18—C17—C16120.9 (2)
C1—C6—C7106.32 (17)C18—C17—H17119.6
C8—C7—C6106.21 (18)C16—C17—H17119.6
C8—C7—C9121.91 (19)C17—C18—C19118.6 (2)
C6—C7—C9131.53 (18)C17—C18—H18120.7
N1—C8—C7110.38 (19)C19—C18—H18120.7
N1—C8—H8124.8C18—C19—C14119.48 (19)
C7—C8—H8124.8C18—C19—C12133.64 (19)
N2—C9—C7123.41 (18)C14—C19—C12106.88 (19)
C9—N2—N3—C10179.52 (17)N2—N3—C10—O10.7 (3)
C8—N1—C1—C2174.9 (2)N2—N3—C10—C11178.41 (15)
C8—N1—C1—C62.0 (2)O1—C10—C11—C1279.3 (2)
N1—C1—C2—C3179.0 (2)N3—C10—C11—C1298.44 (19)
C6—C1—C2—C32.4 (3)C10—C11—C12—C1319.5 (3)
C1—C2—C3—C41.5 (3)C10—C11—C12—C19160.15 (19)
C2—C3—C4—C53.2 (3)C19—C12—C13—N40.6 (3)
C2—C3—C4—Cl1175.50 (17)C11—C12—C13—N4179.7 (2)
C3—C4—C5—C60.8 (3)C14—N4—C13—C121.4 (3)
Cl1—C4—C5—C6177.92 (14)C13—N4—C14—C15179.1 (3)
C4—C5—C6—C13.1 (3)C13—N4—C14—C191.7 (3)
C4—C5—C6—C7176.6 (2)N4—C14—C15—C16179.2 (3)
N1—C1—C6—C5177.93 (17)C19—C14—C15—C160.0 (4)
C2—C1—C6—C54.8 (3)C14—C15—C16—C170.9 (4)
N1—C1—C6—C72.3 (2)C15—C16—C17—C180.9 (4)
C2—C1—C6—C7174.9 (2)C16—C17—C18—C190.1 (4)
C5—C6—C7—C8178.5 (2)C17—C18—C19—C141.0 (3)
C1—C6—C7—C81.8 (2)C17—C18—C19—C12179.4 (2)
C5—C6—C7—C98.3 (4)N4—C14—C19—C18178.4 (2)
C1—C6—C7—C9171.4 (2)C15—C14—C19—C180.9 (3)
C1—N1—C8—C70.9 (3)N4—C14—C19—C121.3 (3)
C6—C7—C8—N10.6 (2)C15—C14—C19—C12179.4 (2)
C9—C7—C8—N1173.38 (19)C13—C12—C19—C18179.2 (2)
N3—N2—C9—C7175.66 (17)C11—C12—C19—C181.1 (4)
C8—C7—C9—N2178.32 (19)C13—C12—C19—C140.4 (2)
C6—C7—C9—N29.5 (3)C11—C12—C19—C14179.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.88 (1)2.02 (1)2.893 (2)174 (3)
N3—H3N···O1ii0.88 (1)1.96 (1)2.827 (2)170 (4)
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x, y+1, z1/2.
 

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