2-Methyl-1H-indole-3-carbaldehyde 4-hydroxybenzoyl­hydrazone

The NH group of the methyl­indole­carbaldehyde moiety and the OH group of the hydroxy­benzoyl­hydrazone moiety of the title compound, C₁₇H₁₅N₃O₂, inter­act to form a linear chain; adjacent chains are linked through the amide –N(H)—C(=O)– portion of the mol­ecule to form a tightly held three-dimensional network structure.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.043
• wR factor = 0.124
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........    H2<I>O<
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........    H1<I>N<
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........    H3<I>N<

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

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.

2-Methyl-1H-indole-3-carbaldehyde 4-hydrobenzoylhydrazone

Crystal data

C17H15N3O2	F(000) = 616
Mr = 293.32	Dx = 1.322 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3602 reflections
a = 12.171 (1) Å	θ = 2.7–27.1°
b = 14.090 (1) Å	µ = 0.09 mm^−1
c = 8.6767 (7) Å	T = 295 K
β = 97.917 (1)°	Block, yellow
V = 1473.8 (2) Å^3	0.31 × 0.27 × 0.24 mm
Z = 4

Data collection

Bruker APEX-II area-detector diffractometer	2516 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 27.1°, θmin = 1.7°
φ and ω scans	h = −15→15
13436 measured reflections	k = −18→17
3236 independent reflections	l = −11→11

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0604P)^2 + 0.3578P] where P = (Fo^2 + 2Fc^2)/3
3236 reflections	(Δ/σ)max = 0.001
212 parameters	Δρmax = 0.22 e Å^−3
3 restraints	Δρmin = −0.18 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.84504 (9)	0.34132 (7)	0.17384 (13)	0.0409 (3)
O2	1.20818 (10)	0.01865 (9)	0.24474 (17)	0.0573 (4)
N1	0.38547 (11)	0.41537 (10)	0.57821 (17)	0.0414 (3)
N2	0.69363 (10)	0.31756 (9)	0.37014 (15)	0.0384 (3)
N3	0.79539 (10)	0.27054 (10)	0.38769 (15)	0.0375 (3)
C1	0.35856 (12)	0.40528 (11)	0.41970 (19)	0.0397 (4)
C2	0.25948 (13)	0.42349 (13)	0.3244 (2)	0.0504 (4)
H2	0.1983	0.4477	0.3648	0.060*
C3	0.25515 (15)	0.40439 (14)	0.1683 (2)	0.0551 (5)
H3	0.1899	0.4161	0.1018	0.066*
C4	0.34674 (15)	0.36786 (14)	0.1077 (2)	0.0529 (5)
H4	0.3408	0.3541	0.0021	0.063*
C5	0.44613 (14)	0.35180 (12)	0.20179 (19)	0.0441 (4)
H5	0.5073	0.3289	0.1599	0.053*
C6	0.45318 (12)	0.37055 (10)	0.36088 (18)	0.0363 (3)
C7	0.53855 (12)	0.36143 (10)	0.49330 (18)	0.0352 (3)
C8	0.49272 (13)	0.38906 (11)	0.62371 (18)	0.0372 (3)
C9	0.54119 (15)	0.39250 (13)	0.79001 (19)	0.0476 (4)
H9A	0.5161	0.4487	0.8370	0.071*
H9B	0.6206	0.3935	0.7981	0.071*
H9C	0.5182	0.3375	0.8426	0.071*
C10	0.64946 (12)	0.32637 (11)	0.49603 (18)	0.0373 (3)
H10	0.6903	0.3096	0.5907	0.045*
C11	0.86110 (12)	0.27882 (10)	0.27744 (17)	0.0334 (3)
C12	0.95165 (12)	0.20881 (10)	0.27749 (17)	0.0344 (3)
C13	1.04665 (14)	0.23511 (12)	0.2159 (2)	0.0520 (5)
H13	1.0531	0.2968	0.1802	0.062*
C14	1.13141 (15)	0.17167 (13)	0.2066 (3)	0.0592 (5)
H14	1.1950	0.1911	0.1672	0.071*
C15	1.12213 (13)	0.07866 (11)	0.2561 (2)	0.0418 (4)
C16	1.02722 (13)	0.05080 (11)	0.31556 (19)	0.0408 (4)
H16	1.0199	−0.0116	0.3478	0.049*
C17	0.94358 (12)	0.11526 (11)	0.32704 (19)	0.0395 (4)
H17	0.8807	0.0960	0.3685	0.047*
H2O	1.195 (2)	−0.0380 (9)	0.272 (3)	0.085 (8)*
H1N	0.3430 (14)	0.4410 (13)	0.6382 (19)	0.056 (5)*
H3N	0.8115 (17)	0.2345 (13)	0.4680 (17)	0.064 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0442 (6)	0.0365 (6)	0.0452 (6)	0.0036 (5)	0.0178 (5)	0.0029 (5)
O2	0.0452 (7)	0.0382 (7)	0.0968 (10)	0.0081 (5)	0.0398 (7)	0.0134 (7)
N1	0.0371 (7)	0.0389 (7)	0.0523 (8)	0.0045 (6)	0.0212 (6)	−0.0001 (6)
N2	0.0318 (7)	0.0411 (7)	0.0442 (7)	0.0067 (5)	0.0116 (5)	0.0037 (6)
N3	0.0323 (7)	0.0438 (8)	0.0380 (7)	0.0089 (6)	0.0109 (5)	0.0041 (6)
C1	0.0346 (8)	0.0332 (8)	0.0538 (10)	0.0003 (6)	0.0153 (7)	0.0024 (7)
C2	0.0333 (8)	0.0500 (10)	0.0698 (12)	0.0030 (7)	0.0136 (8)	0.0055 (9)
C3	0.0391 (9)	0.0592 (12)	0.0652 (12)	−0.0016 (8)	0.0005 (8)	0.0076 (9)
C4	0.0515 (10)	0.0558 (11)	0.0509 (10)	−0.0045 (8)	0.0052 (8)	−0.0012 (8)
C5	0.0441 (9)	0.0412 (9)	0.0493 (10)	0.0031 (7)	0.0139 (7)	−0.0009 (7)
C6	0.0343 (8)	0.0293 (7)	0.0475 (9)	0.0002 (6)	0.0135 (7)	0.0020 (6)
C7	0.0339 (8)	0.0307 (7)	0.0438 (8)	0.0008 (6)	0.0154 (6)	0.0023 (6)
C8	0.0379 (8)	0.0297 (7)	0.0474 (9)	0.0002 (6)	0.0179 (7)	0.0031 (6)
C9	0.0540 (10)	0.0449 (9)	0.0470 (10)	0.0046 (8)	0.0183 (8)	0.0011 (7)
C10	0.0346 (8)	0.0387 (8)	0.0400 (8)	0.0038 (6)	0.0103 (6)	0.0017 (6)
C11	0.0319 (7)	0.0343 (8)	0.0349 (7)	−0.0033 (6)	0.0081 (6)	−0.0028 (6)
C12	0.0315 (7)	0.0365 (8)	0.0366 (8)	−0.0002 (6)	0.0097 (6)	−0.0020 (6)
C13	0.0435 (9)	0.0355 (9)	0.0830 (13)	−0.0001 (7)	0.0301 (9)	0.0101 (8)
C14	0.0423 (9)	0.0431 (10)	0.1009 (15)	0.0023 (8)	0.0403 (10)	0.0140 (10)
C15	0.0367 (8)	0.0369 (8)	0.0554 (10)	0.0014 (6)	0.0192 (7)	0.0027 (7)
C16	0.0393 (8)	0.0329 (8)	0.0533 (10)	−0.0010 (6)	0.0176 (7)	0.0050 (7)
C17	0.0342 (8)	0.0395 (8)	0.0484 (9)	−0.0047 (6)	0.0181 (7)	0.0020 (7)

Geometric parameters (Å, º)

O1—C11	1.2543 (18)	C6—C7	1.445 (2)
O2—C15	1.3603 (19)	C7—C8	1.385 (2)
O2—H2O	0.854 (10)	C7—C10	1.435 (2)
N1—C8	1.362 (2)	C8—C9	1.483 (2)
N1—C1	1.377 (2)	C9—H9A	0.9600
N1—H1N	0.862 (9)	C9—H9B	0.9600
N2—C10	1.2881 (19)	C9—H9C	0.9600
N2—N3	1.3943 (17)	C10—H10	0.9300
N3—C11	1.3338 (18)	C11—C12	1.479 (2)
N3—H3N	0.863 (9)	C12—C13	1.389 (2)
C1—C2	1.389 (2)	C12—C17	1.394 (2)
C1—C6	1.410 (2)	C13—C14	1.376 (2)
C2—C3	1.375 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.388 (2)
C3—C4	1.395 (3)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.385 (2)
C4—C5	1.381 (2)	C16—C17	1.378 (2)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.396 (2)	C17—H17	0.9300
C5—H5	0.9300
C15—O2—H2O	112.8 (16)	C7—C8—C9	130.80 (15)
C8—N1—C1	110.37 (12)	C8—C9—H9A	109.5
C8—N1—H1N	124.7 (13)	C8—C9—H9B	109.5
C1—N1—H1N	124.5 (13)	H9A—C9—H9B	109.5
C10—N2—N3	114.92 (13)	C8—C9—H9C	109.5
C11—N3—N2	119.44 (13)	H9A—C9—H9C	109.5
C11—N3—H3N	122.6 (14)	H9B—C9—H9C	109.5
N2—N3—H3N	117.9 (14)	N2—C10—C7	121.39 (14)
N1—C1—C2	130.03 (14)	N2—C10—H10	119.3
N1—C1—C6	107.68 (14)	C7—C10—H10	119.3
C2—C1—C6	122.29 (16)	O1—C11—N3	121.72 (13)
C3—C2—C1	117.55 (16)	O1—C11—C12	120.73 (13)
C3—C2—H2	121.2	N3—C11—C12	117.51 (13)
C1—C2—H2	121.2	C13—C12—C17	117.94 (14)
C2—C3—C4	121.29 (17)	C13—C12—C11	118.79 (14)
C2—C3—H3	119.4	C17—C12—C11	123.13 (13)
C4—C3—H3	119.4	C14—C13—C12	121.32 (15)
C5—C4—C3	121.20 (18)	C14—C13—H13	119.3
C5—C4—H4	119.4	C12—C13—H13	119.3
C3—C4—H4	119.4	C13—C14—C15	120.10 (15)
C4—C5—C6	118.85 (16)	C13—C14—H14	120.0
C4—C5—H5	120.6	C15—C14—H14	120.0
C6—C5—H5	120.6	O2—C15—C16	122.75 (14)
C5—C6—C1	118.78 (15)	O2—C15—C14	117.90 (14)
C5—C6—C7	135.14 (14)	C16—C15—C14	119.35 (15)
C1—C6—C7	106.07 (13)	C17—C16—C15	120.16 (14)
C8—C7—C10	124.58 (15)	C17—C16—H16	119.9
C8—C7—C6	107.35 (13)	C15—C16—H16	119.9
C10—C7—C6	128.01 (14)	C16—C17—C12	121.11 (13)
N1—C8—C7	108.52 (14)	C16—C17—H17	119.4
N1—C8—C9	120.68 (13)	C12—C17—H17	119.4
C10—N2—N3—C11	−162.72 (14)	C10—C7—C8—C9	1.5 (3)
C8—N1—C1—C2	179.97 (16)	C6—C7—C8—C9	178.87 (16)
C8—N1—C1—C6	0.17 (17)	N3—N2—C10—C7	−171.49 (13)
N1—C1—C2—C3	−178.33 (17)	C8—C7—C10—N2	−167.68 (15)
C6—C1—C2—C3	1.4 (2)	C6—C7—C10—N2	15.5 (2)
C1—C2—C3—C4	0.1 (3)	N2—N3—C11—O1	14.1 (2)
C2—C3—C4—C5	−1.7 (3)	N2—N3—C11—C12	−163.49 (13)
C3—C4—C5—C6	1.6 (3)	O1—C11—C12—C13	29.9 (2)
C4—C5—C6—C1	−0.1 (2)	N3—C11—C12—C13	−152.55 (15)
C4—C5—C6—C7	178.47 (17)	O1—C11—C12—C17	−145.73 (15)
N1—C1—C6—C5	178.33 (14)	N3—C11—C12—C17	31.9 (2)
C2—C1—C6—C5	−1.5 (2)	C17—C12—C13—C14	−1.3 (3)
N1—C1—C6—C7	−0.60 (16)	C11—C12—C13—C14	−177.11 (18)
C2—C1—C6—C7	179.59 (15)	C12—C13—C14—C15	1.4 (3)
C5—C6—C7—C8	−177.86 (17)	C13—C14—C15—O2	−179.96 (18)
C1—C6—C7—C8	0.80 (16)	C13—C14—C15—C16	−0.4 (3)
C5—C6—C7—C10	−0.6 (3)	O2—C15—C16—C17	178.75 (16)
C1—C6—C7—C10	178.03 (14)	C14—C15—C16—C17	−0.8 (3)
C1—N1—C8—C7	0.35 (18)	C15—C16—C17—C12	0.9 (3)
C1—N1—C8—C9	−179.28 (14)	C13—C12—C17—C16	0.1 (2)
C10—C7—C8—N1	−178.06 (13)	C11—C12—C17—C16	175.72 (15)
C6—C7—C8—N1	−0.72 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2o···O1^i	0.85 (1)	1.85 (1)	2.700 (2)	175 (2)
N1—H1n···O2^ii	0.86 (1)	2.07 (1)	2.910 (2)	164 (2)
N3—H3n···O1^iii	0.86 (1)	2.07 (1)	2.933 (2)	174 (2)

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