5-Bromo-1H-indole-3-carb­aldehyde 2-thienoyl­hydrazone

In the title mol­ecule, C₁₄H₁₀BrN₃OS, the indole moiety is twisted by 36.0 (2)° with respect to the disordered thienyl group and the nitro­gen-bound H atoms interact with the amide O atoms of symmetry-related mol­ecules, resulting in an N—H...O hydrogen-bonded layer structure.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.053
• wR factor = 0.151
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)          >H1

Author Response: This is an artifact of the disorder in the thienyl ring, which was refined as S1-C1-C2-C3,C4 and S1'-C1'-C2'-C3'-C4.

PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)          >H2

Author Response: This is an artifact of the disorder in the thienyl ring, which was refined as S1-C1-C2-C3,C4 and S1'-C1'-C2'-C3'-C4.

PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)          >H3

Author Response: This is an artifact of the disorder in the thienyl ring, which was refined as S1-C1-C2-C3,C4 and S1'-C1'-C2'-C3'-C4.

PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)         <H1'

Author Response: This is an artifact of the disorder in the thienyl ring, which was refined as S1-C1-C2-C3,C4 and S1'-C1'-C2'-C3'-C4.

PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)         <H2'

Author Response: This is an artifact of the disorder in the thienyl ring, which was refined as S1-C1-C2-C3,C4 and S1'-C1'-C2'-C3'-C4.

PLAT305_ALERT_2_A Isolated Hydrogen Atom (Outside Bond Range ??)         <H3'

Author Response: This is an artifact of the disorder in the thienyl ring, which was refined as S1-C1-C2-C3,C4 and S1'-C1'-C2'-C3'-C4.

Alert level B
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.71

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.178     0.293
            Tmin' and Tmax expected:      0.216     0.293
            RR' =      0.824
            Please check that your absorption correction is appropriate.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT301_ALERT_3_C Main Residue  Disorder .........................      17.00 Perc.

   6 ALERT level A = In general: serious problem
   1 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
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

5-Bromo-1H-indole-3-carbaldehyde 2-thienoylhydrazone

Crystal data

C14H10BrN3OS	F(000) = 1392
Mr = 348.22	Dx = 1.645 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4416 reflections
a = 7.3437 (4) Å	θ = 2.3–27.1°
b = 17.944 (1) Å	µ = 3.07 mm^−1
c = 21.340 (1) Å	T = 295 K
V = 2812.1 (3) Å^3	Block, yellow
Z = 8	0.48 × 0.42 × 0.40 mm

Data collection

Bruker SMART area-detector diffractometer	3073 independent reflections
Radiation source: medium-focus sealed tube	2135 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 27.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→5
Tmin = 0.178, Tmax = 0.293	k = −22→22
15764 measured reflections	l = −25→27

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.151	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0609P)^2 + 8.173P] where P = (Fo^2 + 2Fc^2)/3
3073 reflections	(Δ/σ)max = 0.001
194 parameters	Δρmax = 1.55 e Å^−3
111 restraints	Δρmin = −1.62 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	1.02049 (8)	0.81548 (3)	0.30123 (4)	0.0810 (3)
S1	1.0480 (3)	0.63318 (13)	0.45490 (7)	0.0580 (6)	0.81 (1)
S1'	0.9553 (14)	0.6308 (7)	0.5862 (4)	0.0580 (6)	0.19
O1	0.6683 (4)	0.53474 (19)	0.55821 (12)	0.0491 (8)
N1	0.6990 (5)	0.5259 (2)	0.45473 (13)	0.0388 (8)
H1n	0.6164	0.4919	0.4543	0.047*
N2	0.7699 (4)	0.55013 (18)	0.39804 (13)	0.0333 (7)
N3	0.7845 (5)	0.5284 (2)	0.18365 (14)	0.0440 (9)
H3n	0.7770	0.5123	0.1458	0.053*
C1	1.1918 (9)	0.6756 (4)	0.5056 (3)	0.060 (2)	0.81 (1)
H1	1.2946	0.7017	0.4927	0.072*	0.807 (5)
C2	1.1453 (9)	0.6683 (4)	0.5655 (3)	0.060 (2)	0.81 (1)
H2	1.2098	0.6878	0.5992	0.072*	0.807 (5)
C3	0.9856 (11)	0.6272 (6)	0.5701 (3)	0.062 (2)	0.81 (1)
H3	0.9303	0.6174	0.6084	0.074*	0.807 (5)
C1'	1.108 (3)	0.6922 (14)	0.5562 (15)	0.060 (2)	0.19
H1'	1.1679	0.7252	0.5828	0.072*	0.193 (5)
C2'	1.143 (4)	0.6935 (18)	0.4951 (14)	0.060 (2)	0.19
H2'	1.2217	0.7244	0.4731	0.072*	0.193 (5)
C3'	1.031 (4)	0.637 (2)	0.4724 (12)	0.062 (2)	0.19
H3'	1.0339	0.6230	0.4304	0.074*	0.193 (5)
C4	0.9143 (6)	0.6017 (2)	0.51413 (16)	0.0387 (9)
C5	0.7531 (6)	0.5529 (2)	0.50999 (16)	0.0364 (9)
C6	0.7242 (5)	0.5100 (2)	0.35109 (16)	0.0305 (8)
H6	0.6606	0.4659	0.3578	0.037*
C7	0.7690 (5)	0.5317 (2)	0.28810 (15)	0.0284 (8)
C8	0.7362 (6)	0.4893 (2)	0.23557 (16)	0.0371 (9)
H8	0.6884	0.4413	0.2356	0.045*
C9	0.8470 (5)	0.5975 (3)	0.20111 (17)	0.0381 (9)
C10	0.9089 (6)	0.6573 (3)	0.1653 (2)	0.0548 (13)
H10	0.9152	0.6540	0.1218	0.066*
C11	0.9597 (7)	0.7208 (3)	0.1956 (3)	0.0586 (14)
H11	1.0004	0.7617	0.1727	0.070*
C12	0.9512 (6)	0.7248 (2)	0.2605 (2)	0.0470 (11)
C13	0.8934 (5)	0.6668 (2)	0.29728 (19)	0.0352 (8)
H13	0.8896	0.6708	0.3407	0.042*
C14	0.8406 (5)	0.6016 (2)	0.26676 (15)	0.0293 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0537 (3)	0.0305 (3)	0.1588 (8)	−0.0001 (2)	0.0249 (4)	0.0018 (3)
S1	0.0552 (10)	0.0886 (13)	0.0303 (9)	−0.0328 (9)	0.0080 (7)	−0.0111 (8)
S1'	0.0552 (10)	0.0886 (13)	0.0303 (9)	−0.0328 (9)	0.0080 (7)	−0.0111 (8)
O1	0.0520 (18)	0.075 (2)	0.0202 (13)	−0.0126 (17)	0.0040 (12)	0.0070 (13)
N1	0.044 (2)	0.051 (2)	0.0205 (15)	−0.0166 (17)	0.0029 (14)	0.0039 (14)
N2	0.0384 (18)	0.0425 (18)	0.0190 (14)	−0.0074 (15)	0.0029 (13)	0.0039 (13)
N3	0.040 (2)	0.072 (3)	0.0196 (15)	0.0074 (19)	−0.0014 (14)	−0.0062 (16)
C1	0.044 (4)	0.080 (4)	0.054 (4)	−0.015 (3)	0.003 (3)	−0.009 (3)
C2	0.048 (3)	0.081 (4)	0.050 (4)	−0.010 (3)	−0.003 (3)	−0.026 (3)
C3	0.063 (4)	0.097 (5)	0.026 (3)	−0.011 (3)	0.009 (3)	−0.021 (3)
C1'	0.044 (4)	0.080 (4)	0.054 (4)	−0.015 (3)	0.003 (3)	−0.009 (3)
C2'	0.048 (3)	0.081 (4)	0.050 (4)	−0.010 (3)	−0.003 (3)	−0.026 (3)
C3'	0.063 (4)	0.097 (5)	0.026 (3)	−0.011 (3)	0.009 (3)	−0.021 (3)
C4	0.038 (2)	0.050 (2)	0.0277 (19)	−0.0002 (19)	0.0035 (17)	−0.0058 (17)
C5	0.040 (2)	0.049 (2)	0.0210 (17)	−0.0019 (18)	0.0001 (16)	0.0044 (16)
C6	0.0343 (19)	0.0330 (18)	0.0243 (17)	−0.0030 (16)	0.0008 (15)	0.0028 (15)
C7	0.0298 (18)	0.0328 (18)	0.0225 (16)	0.0018 (15)	0.0010 (14)	−0.0007 (14)
C8	0.036 (2)	0.047 (2)	0.0280 (19)	0.0030 (18)	0.0007 (17)	−0.0054 (17)
C9	0.0283 (19)	0.059 (3)	0.0268 (18)	0.0110 (18)	0.0023 (15)	0.0078 (18)
C10	0.040 (2)	0.084 (3)	0.041 (2)	0.017 (2)	0.013 (2)	0.033 (2)
C11	0.044 (2)	0.059 (3)	0.072 (3)	0.013 (2)	0.018 (2)	0.040 (3)
C12	0.031 (2)	0.035 (2)	0.074 (3)	0.0064 (17)	0.011 (2)	0.016 (2)
C13	0.0302 (19)	0.0321 (19)	0.043 (2)	0.0045 (15)	0.0054 (17)	0.0055 (17)
C14	0.0256 (17)	0.0395 (19)	0.0228 (17)	0.0063 (15)	0.0041 (14)	0.0064 (15)

Geometric parameters (Å, º)

Br1—C12	1.914 (5)	C1'—H1'	0.9300
S1—C1	1.692 (7)	C2'—C3'	1.396 (14)
S1—C4	1.697 (4)	C2'—H2'	0.9300
S1'—C4	1.653 (7)	C3'—C4	1.386 (13)
S1'—C1'	1.698 (12)	C3'—H3'	0.9300
O1—C5	1.246 (4)	C4—C5	1.475 (6)
N1—C5	1.336 (5)	C6—C7	1.438 (5)
N1—N2	1.387 (4)	C6—H6	0.9300
N1—H1n	0.8600	C7—C8	1.376 (5)
N2—C6	1.279 (5)	C7—C14	1.434 (5)
N3—C8	1.358 (5)	C8—H8	0.9300
N3—C9	1.374 (6)	C9—C10	1.394 (6)
N3—H3n	0.8600	C9—C14	1.404 (5)
C1—C2	1.329 (8)	C10—C11	1.362 (8)
C1—H1	0.9300	C10—H10	0.9300
C2—C3	1.389 (10)	C11—C12	1.388 (7)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.382 (8)	C12—C13	1.371 (6)
C3—H3	0.9300	C13—C14	1.394 (5)
C1'—C2'	1.329 (12)	C13—H13	0.9300
C1—S1—C4	92.0 (3)	C5—C4—S1	128.1 (3)
C4—S1'—C1'	88.5 (13)	O1—C5—N1	119.0 (4)
C5—N1—N2	123.0 (3)	O1—C5—C4	120.5 (3)
C5—N1—H1n	118.5	N1—C5—C4	120.5 (3)
N2—N1—H1n	118.5	N2—C6—C7	121.3 (3)
C6—N2—N1	114.1 (3)	N2—C6—H6	119.3
C8—N3—C9	109.4 (3)	C7—C6—H6	119.3
C8—N3—H3n	125.3	C8—C7—C14	106.8 (3)
C9—N3—H3n	125.3	C8—C7—C6	124.9 (4)
C2—C1—S1	114.2 (6)	C14—C7—C6	128.2 (3)
C2—C1—H1	122.9	N3—C8—C7	109.5 (4)
S1—C1—H1	122.9	N3—C8—H8	125.2
C1—C2—C3	109.7 (6)	C7—C8—H8	125.2
C1—C2—H2	125.1	N3—C9—C10	130.9 (4)
C3—C2—H2	125.1	N3—C9—C14	107.9 (3)
C4—C3—C2	115.8 (6)	C10—C9—C14	121.2 (4)
C4—C3—H3	122.1	C11—C10—C9	118.2 (4)
C2—C3—H3	122.1	C11—C10—H10	120.9
C2'—C1'—S1'	121 (3)	C9—C10—H10	120.9
C2'—C1'—H1'	119.7	C10—C11—C12	120.3 (4)
S1'—C1'—H1'	119.7	C10—C11—H11	119.8
C1'—C2'—C3'	102 (3)	C12—C11—H11	119.8
C1'—C2'—H2'	128.8	C13—C12—C11	123.1 (5)
C3'—C2'—H2'	128.8	C13—C12—Br1	117.9 (4)
C4—C3'—C2'	118 (2)	C11—C12—Br1	119.0 (3)
C4—C3'—H3'	120.9	C12—C13—C14	117.1 (4)
C2'—C3'—H3'	120.9	C12—C13—H13	121.4
C3—C4—C5	123.5 (4)	C14—C13—H13	121.4
C3'—C4—C5	136.6 (13)	C13—C14—C9	120.0 (4)
C3'—C4—S1'	110.0 (14)	C13—C14—C7	133.4 (3)
C5—C4—S1'	112.9 (4)	C9—C14—C7	106.5 (3)
C3—C4—S1	108.3 (4)
C5—N1—N2—C6	169.2 (4)	C3—C4—C5—N1	−175.2 (6)
C4—S1—C1—C2	−0.6 (6)	C3'—C4—C5—N1	8 (3)
S1—C1—C2—C3	−0.5 (8)	S1'—C4—C5—N1	178.6 (6)
C1—C2—C3—C4	1.7 (10)	S1—C4—C5—N1	2.1 (6)
C4—S1'—C1'—C2'	−2.5 (14)	N1—N2—C6—C7	173.1 (3)
S1'—C1'—C2'—C3'	−0.6 (18)	N2—C6—C7—C8	175.2 (4)
C1'—C2'—C3'—C4	5 (3)	N2—C6—C7—C14	−10.2 (6)
C2—C3—C4—C3'	−6.3 (19)	C9—N3—C8—C7	−0.9 (5)
C2—C3—C4—C5	175.7 (6)	C14—C7—C8—N3	0.5 (4)
C2—C3—C4—S1'	−155 (4)	C6—C7—C8—N3	176.1 (4)
C2—C3—C4—S1	−2.1 (9)	C8—N3—C9—C10	−178.9 (4)
C2'—C3'—C4—C3	−13 (3)	C8—N3—C9—C14	1.0 (4)
C2'—C3'—C4—C5	164.5 (17)	N3—C9—C10—C11	178.6 (4)
C2'—C3'—C4—S1'	−7 (4)	C14—C9—C10—C11	−1.4 (6)
C2'—C3'—C4—S1	−168 (14)	C9—C10—C11—C12	0.6 (7)
C1'—S1'—C4—C3	37 (4)	C10—C11—C12—C13	0.3 (7)
C1'—S1'—C4—C3'	5 (2)	C10—C11—C12—Br1	−179.1 (3)
C1'—S1'—C4—C5	−168.7 (10)	C11—C12—C13—C14	−0.4 (6)
C1'—S1'—C4—S1	8.1 (11)	Br1—C12—C13—C14	179.0 (3)
C1—S1—C4—C3	1.4 (6)	C12—C13—C14—C9	−0.4 (5)
C1—S1—C4—C3'	28 (11)	C12—C13—C14—C7	−177.7 (4)
C1—S1—C4—C5	−176.2 (5)	N3—C9—C14—C13	−178.7 (3)
C1—S1—C4—S1'	7.6 (6)	C10—C9—C14—C13	1.3 (6)
N2—N1—C5—O1	171.6 (4)	N3—C9—C14—C7	−0.7 (4)
N2—N1—C5—C4	−10.2 (6)	C10—C9—C14—C7	179.3 (4)
C3—C4—C5—O1	3.0 (8)	C8—C7—C14—C13	177.7 (4)
C3'—C4—C5—O1	−174 (3)	C6—C7—C14—C13	2.3 (7)
S1'—C4—C5—O1	−3.3 (7)	C8—C7—C14—C9	0.1 (4)
S1—C4—C5—O1	−179.7 (4)	C6—C7—C14—C9	−175.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1^i	0.86	2.16	2.921 (5)	147
N3—H3n···O1^ii	0.86	2.09	2.927 (4)	165

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3/2, −y+1, z−1/2.