2′-[(5-Chloro-1H-indol-3-yl)methyl­ene]-2-(1H-indol-3-yl)acetohydrazide

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

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

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Computing details

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

Crystal data

C19H15ClN4O	F(000) = 728
Mr = 350.80	Dx = 1.392 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 6161 reflections
a = 13.7442 (2) Å	θ = 2.7–33.9°
b = 15.0424 (2) Å	µ = 0.24 mm^−1
c = 8.3120 (1) Å	T = 173 K
β = 103.095 (1)°	Block, yellow
V = 1673.78 (4) Å^3	0.47 × 0.32 × 0.30 mm
Z = 4

Data collection

Bruker APEX II CCD diffractometer	1892 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tube	Rint = 0.059
Graphite monochromator	θmax = 27.5°, θmin = 2.0°
ω scans	h = −17→17
12652 measured reflections	k = −19→19
1928 independent reflections	l = −10→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ^2(Fo^2) + (0.0568P)^2 + 0.0652P] where P = (Fo^2 + 2Fc^2)/3
1928 reflections	(Δ/σ)max = 0.001
238 parameters	Δρmax = 0.24 e Å^−3
5 restraints	Δρmin = −0.22 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.50000 (4)	0.55864 (3)	0.50000 (6)	0.02693 (15)
O1	0.16270 (11)	0.41738 (10)	−0.11024 (17)	0.0199 (3)
N1	0.52187 (14)	0.78206 (12)	−0.0642 (2)	0.0235 (4)
N2	0.28012 (13)	0.55948 (10)	−0.1611 (2)	0.0162 (3)
N3	0.21514 (12)	0.51299 (11)	−0.2862 (2)	0.0164 (3)
N4	−0.14405 (17)	0.52291 (18)	−0.4071 (3)	0.0405 (6)
C1	0.53003 (15)	0.73493 (14)	0.0803 (3)	0.0210 (4)
C2	0.60075 (16)	0.74165 (15)	0.2289 (3)	0.0246 (4)
H2	0.6532	0.7841	0.2430	0.029*
C3	0.59228 (16)	0.68441 (14)	0.3556 (3)	0.0237 (4)
H3	0.6402	0.6862	0.4578	0.028*
C4	0.51301 (15)	0.62402 (13)	0.3327 (3)	0.0197 (4)
C5	0.44329 (14)	0.61484 (12)	0.1845 (2)	0.0176 (4)
H5	0.3907	0.5727	0.1721	0.021*
C6	0.45334 (14)	0.66997 (12)	0.0539 (2)	0.0171 (4)
C7	0.40108 (15)	0.67811 (13)	−0.1164 (2)	0.0187 (4)
C8	0.44595 (17)	0.74773 (13)	−0.1811 (3)	0.0231 (4)
H8	0.4263	0.7685	−0.2916	0.028*
C9	0.32516 (13)	0.62370 (12)	−0.2184 (2)	0.0174 (4)
H9	0.3072	0.6356	−0.3336	0.021*
C10	0.16111 (14)	0.44461 (12)	−0.2519 (3)	0.0152 (4)
C11	0.09218 (14)	0.40324 (13)	−0.4026 (2)	0.0173 (4)
H11A	0.1173	0.4172	−0.5023	0.021*
H11B	0.0922	0.3378	−0.3897	0.021*
C12	−0.01274 (16)	0.43775 (13)	−0.4244 (3)	0.0191 (4)
C13	−0.04244 (18)	0.51355 (17)	−0.3589 (3)	0.0318 (5)
H13	0.0011	0.5540	−0.2898	0.038*
C14	−0.18285 (18)	0.45144 (17)	−0.5027 (3)	0.0286 (5)
C15	−0.28168 (19)	0.4297 (2)	−0.5789 (3)	0.0372 (6)
H15	−0.3356	0.4669	−0.5678	0.045*
C16	−0.29792 (17)	0.3530 (2)	−0.6701 (3)	0.0357 (6)
H16	−0.3644	0.3366	−0.7215	0.043*
C17	−0.21891 (18)	0.29820 (16)	−0.6895 (3)	0.0324 (5)
H17	−0.2327	0.2459	−0.7548	0.039*
C18	−0.12079 (16)	0.31930 (14)	−0.6146 (3)	0.0233 (4)
H18	−0.0674	0.2821	−0.6281	0.028*
C19	−0.10217 (14)	0.39664 (14)	−0.5186 (2)	0.0188 (4)
H1N	0.5651 (19)	0.8209 (16)	−0.085 (4)	0.034 (8)*
H3N	0.205 (3)	0.531 (3)	−0.389 (2)	0.046 (9)*
H4N	−0.179 (2)	0.5663 (17)	−0.377 (5)	0.046 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0305 (3)	0.0286 (3)	0.0199 (2)	−0.0051 (2)	0.00189 (18)	0.00593 (19)
O1	0.0227 (7)	0.0206 (7)	0.0154 (7)	−0.0064 (6)	0.0025 (5)	0.0008 (6)
N1	0.0281 (9)	0.0202 (8)	0.0226 (9)	−0.0103 (7)	0.0066 (7)	0.0010 (7)
N2	0.0148 (7)	0.0172 (8)	0.0150 (8)	−0.0019 (5)	0.0002 (6)	−0.0015 (6)
N3	0.0180 (7)	0.0187 (8)	0.0113 (7)	−0.0031 (6)	0.0004 (6)	−0.0008 (6)
N4	0.0297 (11)	0.0486 (14)	0.0389 (13)	0.0165 (9)	−0.0010 (9)	−0.0188 (10)
C1	0.0224 (10)	0.0188 (9)	0.0229 (10)	−0.0051 (7)	0.0070 (8)	−0.0012 (8)
C2	0.0237 (10)	0.0239 (10)	0.0254 (10)	−0.0102 (8)	0.0038 (8)	−0.0043 (8)
C3	0.0218 (10)	0.0260 (10)	0.0213 (10)	−0.0041 (8)	0.0010 (8)	−0.0029 (8)
C4	0.0235 (10)	0.0181 (9)	0.0175 (9)	−0.0007 (7)	0.0050 (7)	0.0009 (7)
C5	0.0183 (9)	0.0138 (8)	0.0207 (9)	−0.0023 (6)	0.0042 (7)	−0.0016 (7)
C6	0.0159 (8)	0.0153 (8)	0.0202 (9)	−0.0013 (6)	0.0042 (7)	−0.0024 (7)
C7	0.0192 (9)	0.0172 (8)	0.0197 (10)	−0.0028 (7)	0.0042 (7)	0.0011 (7)
C8	0.0255 (10)	0.0219 (10)	0.0214 (10)	−0.0041 (8)	0.0042 (8)	0.0023 (8)
C9	0.0165 (9)	0.0181 (9)	0.0169 (9)	−0.0002 (7)	0.0022 (7)	0.0018 (7)
C10	0.0136 (8)	0.0156 (8)	0.0158 (9)	0.0006 (6)	0.0020 (7)	−0.0020 (6)
C11	0.0171 (9)	0.0180 (9)	0.0156 (8)	−0.0027 (7)	0.0012 (7)	−0.0035 (7)
C12	0.0183 (10)	0.0218 (9)	0.0158 (10)	−0.0011 (7)	0.0008 (8)	0.0001 (7)
C13	0.0288 (12)	0.0332 (12)	0.0291 (11)	0.0060 (9)	−0.0021 (9)	−0.0124 (9)
C14	0.0231 (11)	0.0376 (12)	0.0239 (12)	0.0047 (9)	0.0027 (9)	−0.0022 (9)
C15	0.0179 (11)	0.0584 (17)	0.0331 (14)	0.0090 (10)	0.0010 (10)	0.0016 (12)
C16	0.0177 (10)	0.0506 (15)	0.0341 (13)	−0.0078 (9)	−0.0039 (9)	0.0097 (11)
C17	0.0290 (12)	0.0269 (11)	0.0347 (13)	−0.0107 (9)	−0.0064 (9)	0.0034 (9)
C18	0.0209 (9)	0.0206 (9)	0.0257 (11)	−0.0028 (7)	−0.0005 (8)	0.0026 (8)
C19	0.0171 (8)	0.0226 (9)	0.0156 (8)	−0.0013 (7)	0.0017 (7)	0.0038 (7)

Geometric parameters (Å, º)

Cl1—C4	1.746 (2)	C7—C8	1.384 (3)
O1—C10	1.242 (3)	C7—C9	1.441 (3)
N1—C8	1.356 (3)	C8—H8	0.9500
N1—C1	1.377 (3)	C9—H9	0.9500
N1—H1N	0.877 (10)	C10—C11	1.522 (3)
N2—C9	1.295 (2)	C11—C12	1.504 (3)
N2—N3	1.395 (2)	C11—H11A	0.9900
N3—C10	1.337 (2)	C11—H11B	0.9900
N3—H3N	0.879 (10)	C12—C13	1.365 (3)
N4—C13	1.370 (3)	C12—C19	1.439 (3)
N4—C14	1.371 (4)	C13—H13	0.9500
N4—H4N	0.878 (10)	C14—C15	1.401 (4)
C1—C2	1.392 (3)	C14—C19	1.412 (3)
C1—C6	1.417 (3)	C15—C16	1.370 (4)
C2—C3	1.385 (3)	C15—H15	0.9500
C2—H2	0.9500	C16—C17	1.401 (4)
C3—C4	1.398 (3)	C16—H16	0.9500
C3—H3	0.9500	C17—C18	1.388 (3)
C4—C5	1.385 (3)	C17—H17	0.9500
C5—C6	1.397 (3)	C18—C19	1.401 (3)
C5—H5	0.9500	C18—H18	0.9500
C6—C7	1.441 (3)
C8—N1—C1	109.02 (17)	N2—C9—H9	118.3
C8—N1—H1N	124 (2)	C7—C9—H9	118.3
C1—N1—H1N	126 (2)	O1—C10—N3	124.39 (18)
C9—N2—N3	112.24 (17)	O1—C10—C11	121.30 (17)
C10—N3—N2	121.27 (17)	N3—C10—C11	114.27 (17)
C10—N3—H3N	118 (3)	C12—C11—C10	111.04 (16)
N2—N3—H3N	120 (3)	C12—C11—H11A	109.4
C13—N4—C14	109.0 (2)	C10—C11—H11A	109.4
C13—N4—H4N	125 (3)	C12—C11—H11B	109.4
C14—N4—H4N	126 (3)	C10—C11—H11B	109.4
N1—C1—C2	129.72 (19)	H11A—C11—H11B	108.0
N1—C1—C6	108.02 (18)	C13—C12—C19	106.27 (19)
C2—C1—C6	122.2 (2)	C13—C12—C11	127.24 (19)
C3—C2—C1	117.86 (19)	C19—C12—C11	126.48 (17)
C3—C2—H2	121.1	C12—C13—N4	110.3 (2)
C1—C2—H2	121.1	C12—C13—H13	124.9
C2—C3—C4	119.8 (2)	N4—C13—H13	124.9
C2—C3—H3	120.1	N4—C14—C15	130.9 (2)
C4—C3—H3	120.1	N4—C14—C19	107.5 (2)
C5—C4—C3	123.14 (19)	C15—C14—C19	121.5 (2)
C5—C4—Cl1	118.50 (15)	C16—C15—C14	117.8 (2)
C3—C4—Cl1	118.35 (16)	C16—C15—H15	121.1
C4—C5—C6	117.45 (17)	C14—C15—H15	121.1
C4—C5—H5	121.3	C15—C16—C17	121.7 (2)
C6—C5—H5	121.3	C15—C16—H16	119.2
C5—C6—C1	119.34 (18)	C17—C16—H16	119.2
C5—C6—C7	134.34 (17)	C18—C17—C16	120.9 (2)
C1—C6—C7	106.32 (17)	C18—C17—H17	119.6
C8—C7—C6	106.21 (18)	C16—C17—H17	119.6
C8—C7—C9	121.91 (19)	C17—C18—C19	118.6 (2)
C6—C7—C9	131.53 (18)	C17—C18—H18	120.7
N1—C8—C7	110.38 (19)	C19—C18—H18	120.7
N1—C8—H8	124.8	C18—C19—C14	119.48 (19)
C7—C8—H8	124.8	C18—C19—C12	133.64 (19)
N2—C9—C7	123.41 (18)	C14—C19—C12	106.88 (19)
C9—N2—N3—C10	−179.52 (17)	N2—N3—C10—O1	0.7 (3)
C8—N1—C1—C2	174.9 (2)	N2—N3—C10—C11	178.41 (15)
C8—N1—C1—C6	−2.0 (2)	O1—C10—C11—C12	79.3 (2)
N1—C1—C2—C3	−179.0 (2)	N3—C10—C11—C12	−98.44 (19)
C6—C1—C2—C3	−2.4 (3)	C10—C11—C12—C13	19.5 (3)
C1—C2—C3—C4	−1.5 (3)	C10—C11—C12—C19	−160.15 (19)
C2—C3—C4—C5	3.2 (3)	C19—C12—C13—N4	−0.6 (3)
C2—C3—C4—Cl1	−175.50 (17)	C11—C12—C13—N4	179.7 (2)
C3—C4—C5—C6	−0.8 (3)	C14—N4—C13—C12	1.4 (3)
Cl1—C4—C5—C6	177.92 (14)	C13—N4—C14—C15	179.1 (3)
C4—C5—C6—C1	−3.1 (3)	C13—N4—C14—C19	−1.7 (3)
C4—C5—C6—C7	176.6 (2)	N4—C14—C15—C16	179.2 (3)
N1—C1—C6—C5	−177.93 (17)	C19—C14—C15—C16	0.0 (4)
C2—C1—C6—C5	4.8 (3)	C14—C15—C16—C17	−0.9 (4)
N1—C1—C6—C7	2.3 (2)	C15—C16—C17—C18	0.9 (4)
C2—C1—C6—C7	−174.9 (2)	C16—C17—C18—C19	0.1 (4)
C5—C6—C7—C8	178.5 (2)	C17—C18—C19—C14	−1.0 (3)
C1—C6—C7—C8	−1.8 (2)	C17—C18—C19—C12	179.4 (2)
C5—C6—C7—C9	−8.3 (4)	N4—C14—C19—C18	−178.4 (2)
C1—C6—C7—C9	171.4 (2)	C15—C14—C19—C18	0.9 (3)
C1—N1—C8—C7	0.9 (3)	N4—C14—C19—C12	1.3 (3)
C6—C7—C8—N1	0.6 (2)	C15—C14—C19—C12	−179.4 (2)
C9—C7—C8—N1	−173.38 (19)	C13—C12—C19—C18	179.2 (2)
N3—N2—C9—C7	−175.66 (17)	C11—C12—C19—C18	−1.1 (4)
C8—C7—C9—N2	−178.32 (19)	C13—C12—C19—C14	−0.4 (2)
C6—C7—C9—N2	9.5 (3)	C11—C12—C19—C14	179.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.88 (1)	2.02 (1)	2.893 (2)	174 (3)
N3—H3N···O1^ii	0.88 (1)	1.96 (1)	2.827 (2)	170 (4)

Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x, −y+1, z−1/2.