2-Methyl-1H-indole-3-carbaldehyde 2-thienoylhydrazone

In the title compound, C₁₅H₁₃N₃OS, the amide H atom inter­acts with the amide O atom of an adjacent mol­ecule [N...O = 3.027 (4) Å] to form a zigzag chain that runs along the c axis of the monoclinic unit cell.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.075
• wR factor = 0.209
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4     -   C5      ..       5.60 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT420_ALERT_2_C D-H Without Acceptor       N3     -   H3N    ...          ?

   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

   0 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
   1 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 2-thienoylhydrazone

Crystal data

C15H13N3OS	F(000) = 592
Mr = 283.34	Dx = 1.381 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1415 reflections
a = 11.688 (2) Å	θ = 2.5–20.8°
b = 11.546 (2) Å	µ = 0.24 mm^−1
c = 10.133 (2) Å	T = 295 K
β = 94.694 (2)°	Block, yellow
V = 1362.8 (4) Å^3	0.24 × 0.23 × 0.20 mm
Z = 4

Data collection

Bruker APEX-II area-detector diffractometer	1420 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.078
Graphite monochromator	θmax = 26.4°, θmin = 1.8°
φ and ω scans	h = −14→14
11514 measured reflections	k = −14→14
2793 independent reflections	l = −12→12

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.209	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0979P)^2 + 0.3022P] where P = (Fo^2 + 2Fc^2)/3
2793 reflections	(Δ/σ)max = 0.001
170 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

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

	x	y	z	Uiso*/Ueq
S1	0.45706 (10)	0.92616 (10)	0.73323 (11)	0.0697 (4)
O1	0.6319 (2)	0.7454 (2)	0.7868 (3)	0.0626 (8)
N1	0.6354 (3)	0.6811 (3)	0.5739 (3)	0.0620 (9)
H1N	0.6078	0.6867	0.4929	0.074*
N2	0.7227 (3)	0.6032 (3)	0.6084 (3)	0.0598 (9)
N3	0.9457 (3)	0.2966 (3)	0.4867 (4)	0.0646 (10)
H3N	0.9738	0.2388	0.4466	0.078*
C1	0.3534 (4)	0.9786 (4)	0.6195 (4)	0.0727 (13)
H1	0.3041	1.0391	0.6362	0.087*
C2	0.3516 (4)	0.9229 (4)	0.5044 (5)	0.0769 (14)
H2	0.3005	0.9403	0.4319	0.092*
C3	0.4352 (4)	0.8345 (4)	0.5035 (4)	0.0705 (13)
H3	0.4451	0.7875	0.4308	0.085*
C4	0.4998 (3)	0.8261 (3)	0.6221 (4)	0.0575 (11)
C5	0.5937 (3)	0.7485 (4)	0.6681 (4)	0.0546 (10)
C6	0.7387 (3)	0.5277 (4)	0.5156 (4)	0.0598 (11)
H6	0.6909	0.5286	0.4375	0.072*
C7	0.8302 (3)	0.4424 (3)	0.5327 (4)	0.0540 (10)
C8	0.8477 (3)	0.3562 (4)	0.4427 (4)	0.0591 (11)
C9	0.7834 (4)	0.3214 (4)	0.3167 (4)	0.0749 (13)
H9A	0.7693	0.2395	0.3176	0.112*
H9B	0.8276	0.3403	0.2439	0.112*
H9C	0.7115	0.3620	0.3071	0.112*
C10	0.9917 (2)	0.3428 (2)	0.6028 (2)	0.0592 (11)
C11	1.0898 (2)	0.3142 (2)	0.6830 (3)	0.0719 (13)
H11	1.1366	0.2539	0.6591	0.086*
C12	1.1179 (2)	0.3758 (3)	0.7991 (3)	0.0757 (14)
H12	1.1835	0.3566	0.8528	0.091*
C13	1.0479 (3)	0.4659 (3)	0.8348 (2)	0.0701 (12)
H13	1.0668	0.5071	0.9124	0.084*
C14	0.9499 (2)	0.4946 (2)	0.7545 (3)	0.0629 (12)
H14	0.9031	0.5549	0.7785	0.076*
C15	0.92173 (18)	0.4330 (2)	0.6385 (3)	0.0533 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0737 (8)	0.0623 (8)	0.0727 (8)	0.0066 (6)	0.0034 (6)	−0.0106 (6)
O1	0.0598 (17)	0.0609 (18)	0.0678 (19)	0.0039 (14)	0.0091 (14)	−0.0019 (15)
N1	0.059 (2)	0.066 (2)	0.061 (2)	0.0119 (19)	0.0065 (17)	0.0032 (18)
N2	0.053 (2)	0.051 (2)	0.075 (2)	0.0096 (17)	0.0049 (17)	0.0099 (18)
N3	0.070 (2)	0.043 (2)	0.083 (3)	0.0069 (18)	0.021 (2)	−0.0063 (18)
C1	0.069 (3)	0.067 (3)	0.081 (3)	0.013 (2)	0.002 (2)	−0.004 (3)
C2	0.071 (3)	0.086 (4)	0.072 (3)	0.020 (3)	−0.006 (2)	0.001 (3)
C3	0.071 (3)	0.078 (3)	0.063 (3)	0.009 (3)	0.007 (2)	−0.010 (2)
C4	0.049 (2)	0.054 (3)	0.070 (3)	0.002 (2)	0.008 (2)	0.004 (2)
C5	0.057 (3)	0.054 (3)	0.055 (3)	−0.012 (2)	0.015 (2)	−0.009 (2)
C6	0.060 (3)	0.049 (3)	0.073 (3)	0.001 (2)	0.016 (2)	0.004 (2)
C7	0.056 (2)	0.037 (2)	0.072 (3)	0.0025 (19)	0.020 (2)	0.005 (2)
C8	0.060 (3)	0.047 (2)	0.072 (3)	−0.002 (2)	0.019 (2)	0.006 (2)
C9	0.082 (3)	0.066 (3)	0.078 (3)	−0.007 (3)	0.014 (3)	−0.005 (2)
C10	0.052 (2)	0.042 (2)	0.086 (3)	0.003 (2)	0.019 (2)	0.011 (2)
C11	0.060 (3)	0.045 (3)	0.112 (4)	0.004 (2)	0.019 (3)	0.018 (3)
C12	0.056 (3)	0.078 (3)	0.093 (4)	−0.003 (3)	0.004 (2)	0.026 (3)
C13	0.056 (3)	0.070 (3)	0.085 (3)	−0.006 (2)	0.007 (2)	0.005 (3)
C14	0.054 (3)	0.050 (3)	0.087 (3)	0.004 (2)	0.019 (2)	0.002 (2)
C15	0.055 (2)	0.036 (2)	0.072 (3)	−0.0046 (19)	0.018 (2)	0.005 (2)

Geometric parameters (Å, º)

S1—C1	1.713 (5)	C6—H6	0.9300
S1—C4	1.716 (4)	C7—C8	1.376 (5)
O1—C5	1.249 (4)	C7—C15	1.455 (5)
N1—C5	1.353 (5)	C8—C9	1.483 (6)
N1—N2	1.383 (4)	C9—H9A	0.9600
N1—H1N	0.8600	C9—H9B	0.9600
N2—C6	1.307 (5)	C9—H9C	0.9600
N3—C10	1.362 (4)	C10—C11	1.3900
N3—C8	1.379 (5)	C10—C15	1.3900
N3—H3N	0.8600	C11—C12	1.3900
C1—C2	1.330 (6)	C11—H11	0.9300
C1—H1	0.9300	C12—C13	1.3900
C2—C3	1.413 (6)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.3900
C3—C4	1.370 (5)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.3900
C4—C5	1.463 (6)	C14—H14	0.9300
C6—C7	1.454 (5)
C1—S1—C4	91.4 (2)	C6—C7—C15	128.9 (4)
C5—N1—N2	119.8 (3)	C7—C8—N3	108.1 (4)
C5—N1—H1N	120.1	C7—C8—C9	132.4 (4)
N2—N1—H1N	120.1	N3—C8—C9	119.5 (4)
C6—N2—N1	113.4 (3)	C8—C9—H9A	109.5
C10—N3—C8	110.0 (3)	C8—C9—H9B	109.5
C10—N3—H3N	125.0	H9A—C9—H9B	109.5
C8—N3—H3N	125.0	C8—C9—H9C	109.5
C2—C1—S1	112.2 (4)	H9A—C9—H9C	109.5
C2—C1—H1	123.9	H9B—C9—H9C	109.5
S1—C1—H1	123.9	N3—C10—C11	131.3 (2)
C1—C2—C3	113.2 (4)	N3—C10—C15	108.7 (2)
C1—C2—H2	123.4	C11—C10—C15	120.0
C3—C2—H2	123.4	C12—C11—C10	120.0
C4—C3—C2	112.2 (4)	C12—C11—H11	120.0
C4—C3—H3	123.9	C10—C11—H11	120.0
C2—C3—H3	123.9	C13—C12—C11	120.0
C3—C4—C5	131.9 (4)	C13—C12—H12	120.0
C3—C4—S1	111.0 (3)	C11—C12—H12	120.0
C5—C4—S1	117.0 (3)	C12—C13—C14	120.0
O1—C5—N1	122.8 (4)	C12—C13—H13	120.0
O1—C5—C4	121.6 (4)	C14—C13—H13	120.0
N1—C5—C4	115.6 (4)	C13—C14—C15	120.0
N2—C6—C7	120.9 (4)	C13—C14—H14	120.0
N2—C6—H6	119.6	C15—C14—H14	120.0
C7—C6—H6	119.6	C14—C15—C10	120.0
C8—C7—C6	124.0 (4)	C14—C15—C7	133.9 (2)
C8—C7—C15	107.1 (3)	C10—C15—C7	106.0 (2)
C5—N1—N2—C6	166.6 (3)	C15—C7—C8—C9	179.3 (4)
C4—S1—C1—C2	0.2 (4)	C10—N3—C8—C7	−0.1 (4)
S1—C1—C2—C3	−0.1 (5)	C10—N3—C8—C9	179.5 (3)
C1—C2—C3—C4	−0.1 (6)	C8—N3—C10—C11	−178.9 (2)
C2—C3—C4—C5	179.2 (4)	C8—N3—C10—C15	1.4 (3)
C2—C3—C4—S1	0.2 (5)	N3—C10—C11—C12	−179.7 (3)
C1—S1—C4—C3	−0.2 (3)	C15—C10—C11—C12	0.0
C1—S1—C4—C5	−179.4 (3)	C10—C11—C12—C13	0.0
N2—N1—C5—O1	1.3 (5)	C11—C12—C13—C14	0.0
N2—N1—C5—C4	−178.7 (3)	C12—C13—C14—C15	0.0
C3—C4—C5—O1	−170.6 (4)	C13—C14—C15—C10	0.0
S1—C4—C5—O1	8.3 (5)	C13—C14—C15—C7	−177.6 (3)
C3—C4—C5—N1	9.4 (6)	N3—C10—C15—C14	179.8 (3)
S1—C4—C5—N1	−171.7 (3)	C11—C10—C15—C14	0.0
N1—N2—C6—C7	177.4 (3)	N3—C10—C15—C7	−2.0 (2)
N2—C6—C7—C8	175.9 (4)	C11—C10—C15—C7	178.2 (2)
N2—C6—C7—C15	−7.3 (6)	C8—C7—C15—C14	179.8 (2)
C6—C7—C8—N3	176.1 (3)	C6—C7—C15—C14	2.7 (5)
C15—C7—C8—N3	−1.2 (4)	C8—C7—C15—C10	2.0 (3)
C6—C7—C8—C9	−3.4 (7)	C6—C7—C15—C10	−175.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.86	2.27	3.027 (4)	147

Symmetry code: (i) x, −y+3/2, z−1/2.