2-(1H-Indol-3-yl)-2′-(1H-indol-3-yl­methyl­ene)acetohydrazide

Ali, H.M.; Nazzatush Shimar, J.; Ng, S.W.

doi:10.1107/S1600536807032655

2-(1H-Indol-3-yl)-2′-(1H-indol-3-ylmethylene)acetohydrazide

H. M. Ali, J. Nazzatush Shimar and S. W. Ng

The molecules of the title compound, C₁₉H₁₆N₄O, are linked into a three-dimensional architecture by N—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807032655/hb2473sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807032655/hb2473Isup2.hkl Contains datablock I

CCDC reference: 657736

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R factor = 0.034
wR factor = 0.100
Data-to-parameter ratio = 8.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT420_ALERT_2_C D-H Without Acceptor       N4     -   H4N    ...          ?
PLAT731_ALERT_1_C Bond    Calc     0.87(3), Rep   0.876(10) ......       3.00 su-Ra
              N1   -H1N     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.88(3), Rep   0.883(10) ......       3.00 su-Ra
              N4   -H4N     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.99(3), Rep   0.993(10) ......       3.00 su-Ra
              C4   -H4      1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.87(3), Rep   0.880(10) ......       3.00 su-Ra
              N1   -H1N     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.98(3), Rep   1.980(10) ......       3.00 su-Ra
              H1N  -O1      1.555   3.545

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           30.00
           From the CIF: _reflns_number_total               2340
           Count of symmetry unique reflns         2359
           Completeness (_total/calc)             99.19%
           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         no
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         17

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   6 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
   0 ALERT type 5 Informative message, check

Comment top

A previous study reported 2'-[(5-chloro-1H-indol-3-yl)methylene]-2-(1H-indol-3-yl)acetohydrazide, a compound that is N–H···O hydrogen bonded into a three-dimensional network (Ali et al., 2007). Although there are three possible donor sites, the site belonging to the indolyl ring that is linked to the methylene unit is not involved in the H bond interactions. A similar type of hydrogen bonding (Table 1) is found in the unsubstituted title compound, (I), (Fig. 1).

Related literature top

For a related crystal structure, see Ali et al. (2007).

Experimental top

Indol-3-yl-acetylhydrazine (0.30 g, 1.6 mmol) and indol-3-ylcarboxaldehyde (0.20 g, 1.6 mmol) were heated in ethanol (50 ml) for 2 h. The solution was filtered; slow evaporation of the solvent yielded faint yellow needles of (I).

Structure description top

For a related crystal structure, see Ali et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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).

Figures top

Fig. 1. View of (I) with displacement ellipsoids drawn at the 70% probability level, and H atoms as spheres of arbitrary radius.

2-(1H-Indol-3-yl)-2'-(1H-indol-3-ylmethylene)acetohydrazide top

Crystal data top

C₁₉H₁₆N₄O	F(000) = 664
M_r = 316.36	D_x = 1.303 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 8692 reflections
a = 14.0350 (2) Å	θ = 2.8–30.2°
b = 14.4517 (2) Å	µ = 0.08 mm⁻¹
c = 8.1372 (1) Å	T = 293 K
β = 102.193 (1)°	Tapered needle, light yellow
V = 1613.23 (4) Å³	0.60 × 0.15 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	2260 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 30.0°, θ_min = 2.1°
φ and ω scans	h = −19→19
12370 measured reflections	k = −20→20
2340 independent reflections	l = −11→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0767P)² + 0.0497P] where P = (F_o² + 2F_c²)/3
S = 1.17	(Δ/σ)_max = 0.001
2340 reflections	Δρ_max = 0.38 e Å⁻³
281 parameters	Δρ_min = −0.26 e Å⁻³
17 restraints	Absolute structure: Friedel pairs were merged
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₉H₁₆N₄O	V = 1613.23 (4) Å³
M_r = 316.36	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 14.0350 (2) Å	µ = 0.08 mm⁻¹
b = 14.4517 (2) Å	T = 293 K
c = 8.1372 (1) Å	0.60 × 0.15 × 0.10 mm
β = 102.193 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2260 reflections with I > 2σ(I)
12370 measured reflections	R_int = 0.023
2340 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	17 restraints
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	Δρ_max = 0.38 e Å⁻³
2340 reflections	Δρ_min = −0.26 e Å⁻³
281 parameters	Absolute structure: Friedel pairs were merged

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.50000 (8)	0.58900 (8)	0.50001 (14)	0.0172 (2)
N1	0.86357 (11)	0.22337 (10)	0.56290 (18)	0.0207 (3)
N2	0.62106 (9)	0.44789 (8)	0.44976 (15)	0.0139 (2)
N3	0.55394 (9)	0.49082 (9)	0.32082 (15)	0.0143 (2)
N4	0.20100 (11)	0.47912 (12)	0.2027 (2)	0.0279 (3)
C1	0.87353 (11)	0.28098 (11)	0.7011 (2)	0.0176 (3)
C2	0.94407 (13)	0.28031 (13)	0.8506 (2)	0.0236 (3)
C3	0.93560 (13)	0.34678 (13)	0.9698 (2)	0.0260 (3)
C4	0.85926 (14)	0.41173 (13)	0.9415 (2)	0.0247 (3)
C5	0.79050 (12)	0.41325 (11)	0.7917 (2)	0.0193 (3)
C6	0.79757 (10)	0.34736 (10)	0.66815 (18)	0.0150 (3)
C7	0.78624 (12)	0.25238 (12)	0.44324 (19)	0.0204 (3)
C8	0.74261 (11)	0.32866 (10)	0.50057 (19)	0.0160 (3)
C9	0.66442 (11)	0.37875 (10)	0.39548 (18)	0.0154 (3)
C10	0.49922 (10)	0.56129 (9)	0.35533 (18)	0.0134 (2)
C11	0.43239 (10)	0.60328 (10)	0.20165 (19)	0.0152 (3)
C12	0.30093 (12)	0.48812 (12)	0.2490 (2)	0.0226 (3)
C13	0.33009 (11)	0.56780 (10)	0.18153 (18)	0.0154 (3)
C14	0.24281 (10)	0.61075 (10)	0.08736 (18)	0.0155 (3)
C15	0.22490 (11)	0.69156 (11)	−0.0099 (2)	0.0193 (3)
C16	0.12907 (13)	0.71310 (12)	−0.0859 (2)	0.0246 (3)
C17	0.05120 (13)	0.65631 (15)	−0.0636 (2)	0.0274 (4)
C18	0.06691 (12)	0.57637 (15)	0.0317 (2)	0.0276 (4)
C19	0.16355 (12)	0.55390 (12)	0.1053 (2)	0.0212 (3)
H1n	0.906 (2)	0.1812 (18)	0.551 (4)	0.046 (8)*
H3n	0.5469 (17)	0.4733 (16)	0.2169 (15)	0.017 (5)*
H4n	0.167 (2)	0.4364 (17)	0.242 (4)	0.041 (8)*
H2	0.9927 (18)	0.2299 (16)	0.860 (4)	0.041 (8)*
H3	0.9847 (16)	0.348 (2)	1.079 (2)	0.034 (7)*
H4	0.851 (2)	0.4539 (18)	1.034 (3)	0.041 (7)*
H5	0.7363 (14)	0.4593 (15)	0.772 (3)	0.027 (6)*
H7	0.7666 (19)	0.2195 (16)	0.334 (2)	0.026 (6)*
H9	0.6452 (19)	0.3595 (18)	0.2750 (15)	0.025 (6)*
H11A	0.4299 (18)	0.6713 (7)	0.218 (3)	0.022 (6)*
H11B	0.4619 (17)	0.5947 (18)	0.101 (2)	0.024 (6)*
H12	0.341 (2)	0.439 (2)	0.309 (4)	0.034 (7)*
H15	0.2789 (15)	0.7343 (17)	−0.021 (4)	0.032 (7)*
H16	0.117 (2)	0.7690 (13)	−0.159 (3)	0.037 (8)*
H17	−0.0162 (10)	0.6719 (19)	−0.124 (3)	0.032 (7)*
H18	0.0150 (16)	0.5337 (17)	0.050 (4)	0.037 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0198 (5)	0.0187 (5)	0.0121 (5)	0.0055 (4)	0.0011 (4)	−0.0006 (4)
N1	0.0239 (6)	0.0203 (6)	0.0181 (6)	0.0101 (5)	0.0049 (5)	0.0000 (5)
N2	0.0131 (5)	0.0155 (5)	0.0118 (6)	0.0026 (4)	0.0000 (4)	0.0025 (4)
N3	0.0158 (5)	0.0172 (5)	0.0088 (5)	0.0037 (4)	0.0001 (4)	−0.0002 (4)
N4	0.0196 (7)	0.0330 (8)	0.0278 (7)	−0.0075 (5)	−0.0029 (5)	0.0127 (6)
C1	0.0175 (6)	0.0186 (6)	0.0167 (7)	0.0046 (5)	0.0034 (5)	0.0022 (5)
C2	0.0198 (7)	0.0287 (8)	0.0207 (8)	0.0060 (6)	0.0005 (6)	0.0044 (6)
C3	0.0236 (7)	0.0316 (8)	0.0187 (8)	0.0000 (6)	−0.0046 (6)	−0.0001 (6)
C4	0.0268 (8)	0.0263 (8)	0.0187 (7)	−0.0013 (6)	−0.0007 (6)	−0.0057 (6)
C5	0.0210 (7)	0.0180 (7)	0.0181 (7)	0.0027 (5)	0.0022 (5)	−0.0031 (5)
C6	0.0147 (6)	0.0151 (6)	0.0149 (6)	0.0029 (4)	0.0024 (5)	0.0006 (5)
C7	0.0244 (7)	0.0199 (7)	0.0163 (7)	0.0065 (5)	0.0033 (5)	−0.0023 (5)
C8	0.0174 (6)	0.0157 (6)	0.0141 (6)	0.0040 (5)	0.0017 (5)	−0.0001 (5)
C9	0.0163 (6)	0.0170 (6)	0.0122 (6)	0.0026 (5)	0.0009 (5)	0.0001 (5)
C10	0.0123 (5)	0.0147 (5)	0.0122 (6)	0.0014 (4)	0.0004 (4)	0.0024 (5)
C11	0.0141 (6)	0.0176 (6)	0.0125 (6)	0.0027 (5)	−0.0005 (5)	0.0038 (5)
C12	0.0198 (7)	0.0254 (7)	0.0196 (7)	−0.0031 (6)	−0.0027 (6)	0.0074 (6)
C13	0.0150 (6)	0.0177 (6)	0.0123 (6)	0.0010 (5)	−0.0001 (5)	0.0013 (5)
C14	0.0149 (6)	0.0186 (6)	0.0121 (6)	0.0019 (5)	0.0010 (5)	−0.0014 (5)
C15	0.0189 (7)	0.0195 (6)	0.0180 (7)	0.0048 (5)	0.0005 (5)	0.0001 (5)
C16	0.0222 (8)	0.0244 (7)	0.0246 (8)	0.0086 (6)	−0.0010 (6)	0.0016 (6)
C17	0.0174 (7)	0.0389 (9)	0.0231 (8)	0.0073 (6)	−0.0018 (6)	−0.0001 (7)
C18	0.0157 (7)	0.0402 (9)	0.0250 (8)	−0.0026 (6)	−0.0001 (6)	0.0007 (7)
C19	0.0173 (6)	0.0279 (8)	0.0170 (7)	−0.0019 (5)	0.0005 (5)	0.0032 (6)

Geometric parameters (Å, º) top

O1—C10	1.2414 (19)	C7—C8	1.389 (2)
N1—C7	1.362 (2)	C7—H7	0.996 (10)
N1—C1	1.382 (2)	C8—C9	1.436 (2)
N1—H1n	0.876 (10)	C9—H9	1.000 (10)
N2—C9	1.2952 (18)	C10—C11	1.5220 (19)
N2—N3	1.3985 (16)	C11—C13	1.501 (2)
N3—C10	1.3405 (18)	C11—H11A	0.994 (10)
N3—H3n	0.868 (10)	C11—H11B	1.000 (10)
N4—C19	1.377 (2)	C12—C13	1.375 (2)
N4—C12	1.379 (2)	C12—H12	0.97 (3)
N4—H4n	0.883 (10)	C13—C14	1.4410 (19)
C1—C2	1.397 (2)	C14—C15	1.403 (2)
C1—C6	1.4171 (19)	C14—C19	1.415 (2)
C2—C3	1.388 (3)	C15—C16	1.392 (2)
C2—H2	0.991 (10)	C15—H15	0.996 (10)
C3—C4	1.406 (3)	C16—C17	1.409 (3)
C3—H3	1.002 (10)	C16—H16	0.998 (10)
C4—C5	1.386 (2)	C17—C18	1.383 (3)
C4—H4	0.993 (10)	C17—H17	0.994 (10)
C5—C6	1.404 (2)	C18—C19	1.400 (2)
C5—H5	0.998 (10)	C18—H18	0.991 (10)
C6—C8	1.443 (2)

C7—N1—C1	108.94 (12)	N2—C9—H9	120.0 (16)
C7—N1—H1n	127 (2)	C8—C9—H9	117.2 (16)
C1—N1—H1n	124 (2)	O1—C10—N3	123.58 (13)
C9—N2—N3	112.15 (12)	O1—C10—C11	122.08 (13)
C10—N3—N2	120.32 (12)	N3—C10—C11	114.31 (13)
C10—N3—H3n	118.3 (16)	C13—C11—C10	111.28 (12)
N2—N3—H3n	121.4 (16)	C13—C11—H11A	107.0 (15)
C19—N4—C12	109.00 (14)	C10—C11—H11A	108.4 (14)
C19—N4—H4n	126 (2)	C13—C11—H11B	114.9 (15)
C12—N4—H4n	124 (2)	C10—C11—H11B	109.4 (15)
N1—C1—C2	129.47 (15)	H11A—C11—H11B	106 (2)
N1—C1—C6	108.12 (13)	C13—C12—N4	109.95 (14)
C2—C1—C6	122.40 (15)	C13—C12—H12	128.8 (18)
C3—C2—C1	117.02 (15)	N4—C12—H12	120.8 (18)
C3—C2—H2	128.1 (19)	C12—C13—C14	106.37 (13)
C1—C2—H2	114.8 (19)	C12—C13—C11	126.96 (13)
C2—C3—C4	121.48 (15)	C14—C13—C11	126.67 (13)
C2—C3—H3	118.9 (17)	C15—C14—C19	119.35 (14)
C4—C3—H3	119.6 (17)	C15—C14—C13	133.57 (14)
C5—C4—C3	121.32 (16)	C19—C14—C13	107.08 (13)
C5—C4—H4	119.3 (19)	C16—C15—C14	118.55 (15)
C3—C4—H4	119.2 (19)	C16—C15—H15	120.2 (17)
C4—C5—C6	118.54 (15)	C14—C15—H15	121.2 (17)
C4—C5—H5	121.0 (16)	C15—C16—C17	121.05 (16)
C6—C5—H5	120.4 (16)	C15—C16—H16	117.9 (17)
C5—C6—C1	119.21 (14)	C17—C16—H16	121.1 (17)
C5—C6—C8	134.37 (14)	C18—C17—C16	121.51 (15)
C1—C6—C8	106.42 (13)	C18—C17—H17	119.1 (17)
N1—C7—C8	110.21 (14)	C16—C17—H17	119.3 (17)
N1—C7—H7	121.4 (15)	C17—C18—C19	117.31 (16)
C8—C7—H7	128.4 (15)	C17—C18—H18	124.8 (18)
C7—C8—C9	122.39 (14)	C19—C18—H18	117.9 (18)
C7—C8—C6	106.28 (13)	N4—C19—C18	130.20 (16)
C9—C8—C6	131.06 (13)	N4—C19—C14	107.59 (14)
N2—C9—C8	122.73 (13)	C18—C19—C14	122.20 (16)

C9—N2—N3—C10	177.12 (13)	N2—N3—C10—C11	177.81 (12)
C7—N1—C1—C2	−177.43 (18)	O1—C10—C11—C13	−78.13 (17)
C7—N1—C1—C6	1.60 (18)	N3—C10—C11—C13	99.87 (15)
N1—C1—C2—C3	−179.51 (17)	C19—N4—C12—C13	−0.6 (2)
C6—C1—C2—C3	1.6 (3)	N4—C12—C13—C14	−0.1 (2)
C1—C2—C3—C4	0.2 (3)	N4—C12—C13—C11	179.88 (16)
C2—C3—C4—C5	−1.4 (3)	C10—C11—C13—C12	−20.7 (2)
C3—C4—C5—C6	0.8 (3)	C10—C11—C13—C14	159.29 (14)
C4—C5—C6—C1	0.9 (2)	C12—C13—C14—C15	−179.13 (17)
C4—C5—C6—C8	−178.63 (17)	C11—C13—C14—C15	0.9 (3)
N1—C1—C6—C5	178.76 (14)	C12—C13—C14—C19	0.75 (17)
C2—C1—C6—C5	−2.1 (2)	C11—C13—C14—C19	−179.23 (15)
N1—C1—C6—C8	−1.63 (17)	C19—C14—C15—C16	0.0 (2)
C2—C1—C6—C8	177.48 (15)	C13—C14—C15—C16	179.90 (17)
C1—N1—C7—C8	−0.93 (19)	C14—C15—C16—C17	1.2 (2)
N1—C7—C8—C9	174.55 (14)	C15—C16—C17—C18	−1.1 (3)
N1—C7—C8—C6	−0.11 (19)	C16—C17—C18—C19	−0.1 (3)
C5—C6—C8—C7	−179.41 (17)	C12—N4—C19—C18	−178.80 (19)
C1—C6—C8—C7	1.06 (17)	C12—N4—C19—C14	1.1 (2)
C5—C6—C8—C9	6.6 (3)	C17—C18—C19—N4	−178.77 (19)
C1—C6—C8—C9	−172.95 (16)	C17—C18—C19—C14	1.4 (3)
N3—N2—C9—C8	174.31 (13)	C15—C14—C19—N4	178.78 (15)
C7—C8—C9—N2	177.46 (15)	C13—C14—C19—N4	−1.13 (18)
C6—C8—C9—N2	−9.3 (3)	C15—C14—C19—C18	−1.3 (2)
N2—N3—C10—O1	−4.2 (2)	C13—C14—C19—C18	178.77 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.88 (1)	1.98 (1)	2.848 (2)	174 (3)
N3—H3N···O1ⁱⁱ	0.87 (1)	1.97 (1)	2.808 (2)	163 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₆N₄O
M_r	316.36
Crystal system, space group	Monoclinic, Cc
Temperature (K)	293
a, b, c (Å)	14.0350 (2), 14.4517 (2), 8.1372 (1)
β (°)	102.193 (1)
V (Å³)	1613.23 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.60 × 0.15 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12370, 2340, 2260
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.100, 1.17
No. of reflections	2340
No. of parameters	281
No. of restraints	17
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.26
Absolute structure	Friedel pairs were merged

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).