5-Bromo-1H-indole-3-carbaldehyde 3-methoxy­benzoyl­hydrazone

Mol­ecules of 5-bromo-1H-indole-3-carbaldehyde 3-methoxy­benzoyl­ylhydrazone, C₁₇H₁₄BrN₃O₂, are paired by amino-carbon­yl hydrogen bonds over a center of inversion, and adjacent pairs are further linked by hydrogen bonds into ribbons.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.042
• wR factor = 0.114
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.75
PLAT411_ALERT_2_B Short Inter H...H Contact  H11    ..  H11     ..       2.03 Ang.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.315     0.650
            Tmin(prime) and Tmax expected:      0.392     0.624
            RR(prime) =      0.772
            Please check that your absorption correction is appropriate.
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.96

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   2 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
   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

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Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); 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 3-methoxybenzoylhydrazone

Crystal data

C17H14BrN3O2	F(000) = 1504
Mr = 372.22	Dx = 1.566 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9770 reflections
a = 19.257 (4) Å	θ = 3.1–27.5°
b = 8.904 (3) Å	µ = 2.62 mm^−1
c = 19.400 (4) Å	T = 295 K
β = 108.330 (17)°	Block, brown
V = 3157.7 (13) Å^3	0.35 × 0.24 × 0.18 mm
Z = 8

Data collection

Rigaku R-AXIS RAPID diffractometer	3616 independent reflections
Radiation source: fine-focus sealed tube	2664 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 10 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −24→23
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −11→11
Tmin = 0.315, Tmax = 0.650	l = −25→25
15076 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0492P)^2 + 3.744P] where P = (Fo^2 + 2Fc^2)/3
3616 reflections	(Δ/σ)max = 0.001
216 parameters	Δρmax = 0.49 e Å^−3
2 restraints	Δρmin = −0.75 e Å^−3

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

	x	y	z	Uiso*/Ueq
Br1	0.11452 (2)	0.45712 (4)	0.31863 (2)	0.0762 (2)
O1	0.3015 (1)	0.3651 (2)	0.3544 (1)	0.056 (1)
O2	0.5180 (1)	0.8291 (2)	0.4557 (1)	0.048 (1)
N1	0.4080 (1)	0.9026 (3)	0.4576 (1)	0.040 (1)
N2	0.3324 (1)	0.8879 (2)	0.4355 (1)	0.034 (1)
N3	0.1095 (1)	1.0703 (3)	0.4399 (1)	0.048 (1)
C1	0.3697 (1)	0.5850 (3)	0.3892 (1)	0.034 (1)
C2	0.3447 (1)	0.4716 (3)	0.3383 (1)	0.037 (1)
C3	0.3642 (2)	0.4721 (3)	0.2752 (1)	0.042 (1)
C4	0.4111 (2)	0.5813 (3)	0.2656 (1)	0.043 (1)
C5	0.4388 (1)	0.6896 (3)	0.3171 (1)	0.038 (1)
C6	0.4169 (1)	0.6923 (3)	0.3791 (1)	0.031 (1)
C7	0.2739 (2)	0.2488 (4)	0.3035 (2)	0.072 (1)
C8	0.4509 (1)	0.8117 (3)	0.4339 (1)	0.034 (1)
C9	0.2997 (1)	0.9876 (3)	0.4605 (2)	0.045 (1)
C10	0.2211 (1)	0.9876 (3)	0.4452 (2)	0.040 (1)
C11	0.1817 (2)	1.1039 (4)	0.4603 (2)	0.056 (1)
C12	0.1694 (1)	0.8729 (3)	0.4136 (1)	0.032 (1)
C13	0.1740 (1)	0.7294 (3)	0.3866 (1)	0.036 (1)
C14	0.1107 (2)	0.6500 (3)	0.3594 (2)	0.044 (1)
C15	0.0423 (2)	0.7042 (4)	0.3590 (2)	0.051 (1)
C16	0.0368 (2)	0.8437 (3)	0.3858 (2)	0.046 (1)
C17	0.1001 (1)	0.9280 (3)	0.4122 (1)	0.035 (1)
H1n	0.429 (1)	0.974 (3)	0.487 (1)	0.039 (7)*
H3n	0.079 (2)	1.136 (3)	0.446 (2)	0.056 (9)*
H1	0.3545	0.5883	0.4302	0.041*
H3	0.3458	0.3993	0.2398	0.050*
H4	0.4241	0.5814	0.2233	0.051*
H5	0.4718	0.7603	0.3108	0.045*
H7a	0.2445	0.1820	0.3215	0.108*
H7b	0.3139	0.1940	0.2961	0.108*
H7c	0.2446	0.2913	0.2582	0.108*
H9	0.3272	1.0632	0.4897	0.054*
H11	0.2018	1.1940	0.4816	0.067*
H12	0.2188	0.6892	0.3870	0.043*
H14	0.0007	0.6453	0.3403	0.061*
H15	−0.0081	0.8811	0.3864	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0598 (2)	0.0475 (2)	0.1200 (4)	−0.0120 (2)	0.0264 (2)	−0.0331 (2)
O1	0.062 (1)	0.047 (1)	0.064 (1)	−0.023 (1)	0.028 (1)	−0.015 (1)
O2	0.028 (1)	0.047 (1)	0.068 (1)	0.000 (1)	0.014 (1)	−0.023 (1)
N1	0.027 (1)	0.037 (1)	0.056 (1)	0.000 (1)	0.011 (1)	−0.019 (1)
N2	0.024 (1)	0.033 (1)	0.046 (1)	0.002 (1)	0.009 (1)	−0.009 (1)
N3	0.031 (1)	0.044 (1)	0.068 (2)	0.011 (1)	0.015 (1)	−0.012 (1)
C1	0.029 (1)	0.037 (1)	0.037 (1)	0.000 (1)	0.012 (1)	−0.007 (1)
C2	0.032 (1)	0.032 (1)	0.045 (1)	0.000 (1)	0.012 (1)	−0.004 (1)
C3	0.044 (2)	0.040 (2)	0.039 (1)	0.001 (1)	0.010 (1)	−0.011 (1)
C4	0.047 (2)	0.049 (2)	0.036 (1)	0.002 (1)	0.017 (1)	−0.005 (1)
C5	0.035 (1)	0.036 (1)	0.043 (1)	0.000 (1)	0.016 (1)	−0.002 (1)
C6	0.025 (1)	0.031 (1)	0.037 (1)	0.006 (1)	0.008 (1)	−0.004 (1)
C7	0.073 (2)	0.050 (2)	0.091 (2)	−0.027 (2)	0.024 (2)	−0.023 (2)
C8	0.0259 (1)	0.033 (1)	0.043 (1)	0.002 (1)	0.011 (1)	−0.006 (1)
C9	0.0309 (1)	0.036 (1)	0.066 (2)	0.001 (1)	0.012 (1)	−0.018 (1)
C10	0.028 (1)	0.038 (1)	0.054 (2)	0.006 (1)	0.011 (1)	−0.011 (1)
C11	0.035 (2)	0.041 (2)	0.091 (2)	0.003 (1)	0.016 (2)	−0.026 (2)
C12	0.030 (1)	0.035 (1)	0.032 (1)	0.005 (1)	0.010 (1)	0.003 (1)
C13	0.033 (1)	0.033 (1)	0.041 (1)	0.004 (1)	0.013 (1)	0.001 (1)
C14	0.040 (2)	0.035 (1)	0.054 (2)	0.000 (1)	0.011 (1)	−0.003 (1)
C15	0.034 (2)	0.050 (2)	0.065 (2)	−0.005 (1)	0.011 (1)	0.000 (1)
C16	0.030 (1)	0.051 (2)	0.057 (2)	0.006 (1)	0.012 (1)	0.004 (1)
C17	0.030 (1)	0.039 (1)	0.037 (1)	0.007 (1)	0.010 (1)	0.002 (1)

Geometric parameters (Å, º)

Br1—C14	1.902 (3)	C12—C17	1.414 (3)
O1—C2	1.362 (3)	C13—C14	1.364 (4)
O1—C7	1.415 (4)	C14—C15	1.400 (4)
O2—C8	1.236 (3)	C15—C16	1.364 (4)
N1—C8	1.336 (3)	C16—C17	1.385 (4)
N1—N2	1.388 (3)	N1—H1n	0.87 (2)
N2—C9	1.270 (3)	N3—H3n	0.85 (2)
N3—C11	1.354 (4)	C1—H1	0.93
N3—C17	1.366 (3)	C3—H3	0.93
C1—C6	1.374 (3)	C4—H4	0.93
C1—C2	1.389 (3)	C5—H5	0.93
C2—C3	1.388 (4)	C7—H7a	0.96
C3—C4	1.379 (4)	C7—H7b	0.96
C4—C5	1.371 (4)	C7—H7c	0.96
C5—C6	1.395 (3)	C9—H9	0.93
C6—C8	1.501 (3)	C11—H11	0.93
C9—C10	1.448 (4)	C13—H12	0.93
C10—C11	1.369 (4)	C15—H14	0.93
C10—C12	1.423 (4)	C16—H15	0.93
C12—C13	1.395 (3)
C2—O1—C7	118.1 (2)	N3—C17—C16	129.8 (2)
C8—N1—N2	122.6 (2)	N3—C17—C12	107.8 (2)
C9—N2—N1	114.4 (2)	C16—C17—C12	122.4 (2)
C11—N3—C17	108.4 (2)	C8—N1—H1n	117 (2)
C6—C1—C2	120.1 (2)	N2—N1—H1n	120 (2)
O1—C2—C3	124.0 (2)	C11—N3—H3n	119 (2)
O1—C2—C1	116.3 (2)	C17—N3—H3n	132 (2)
C3—C2—C1	119.7 (2)	C6—C1—H1	120.0
C4—C3—C2	119.5 (2)	C2—C1—H1	120.0
C5—C4—C3	121.2 (2)	C4—C3—H3	120.3
C4—C5—C6	119.1 (2)	C2—C3—H3	120.3
C1—C6—C5	120.3 (2)	C5—C4—H4	119.4
C1—C6—C8	123.5 (2)	C3—C4—H4	119.4
C5—C6—C8	116.1 (2)	C4—C5—H5	120.4
O2—C8—N1	119.9 (2)	C6—C5—H5	120.4
O2—C8—C6	120.5 (2)	O1—C7—H7a	109.5
N1—C8—C6	119.6 (2)	O1—C7—H7b	109.5
N2—C9—C10	122.2 (3)	H7a—C7—H7b	109.5
C11—C10—C12	105.9 (2)	O1—C7—H7c	109.5
C11—C10—C9	124.8 (3)	H7a—C7—H7c	109.5
C12—C10—C9	129.3 (2)	H7b—C7—H7c	109.5
N3—C11—C10	111.0 (3)	N2—C9—H9	118.9
C13—C12—C17	118.8 (2)	C10—C9—H9	118.9
C13—C12—C10	134.4 (2)	N3—C11—H11	124.5
C17—C12—C10	106.8 (2)	C10—C11—H11	124.5
C14—C13—C12	117.7 (2)	C14—C13—H12	121.1
C13—C14—C15	123.3 (3)	C12—C13—H12	121.1
C13—C14—Br1	118.8 (2)	C16—C15—H14	120.1
C15—C14—Br1	117.9 (2)	C14—C15—H14	120.1
C16—C15—C14	119.9 (3)	C15—C16—H15	121.0
C15—C16—C17	118.0 (3)	C17—C16—H15	121.0
C8—N1—N2—C9	−176.9 (3)	C17—N3—C11—C10	1.4 (4)
C7—O1—C2—C3	−0.8 (4)	C12—C10—C11—N3	−0.5 (4)
C7—O1—C2—C1	179.1 (3)	C9—C10—C11—N3	−179.8 (3)
C6—C1—C2—O1	176.5 (2)	C11—C10—C12—C13	179.6 (3)
C6—C1—C2—C3	−3.7 (4)	C9—C10—C12—C13	−1.1 (5)
O1—C2—C3—C4	−177.0 (3)	C11—C10—C12—C17	−0.6 (3)
C1—C2—C3—C4	3.1 (4)	C9—C10—C12—C17	178.7 (3)
C2—C3—C4—C5	0.0 (4)	C17—C12—C13—C14	0.5 (3)
C3—C4—C5—C6	−2.5 (4)	C10—C12—C13—C14	−179.7 (3)
C2—C1—C6—C5	1.2 (4)	C12—C13—C14—C15	−1.4 (4)
C2—C1—C6—C8	−175.3 (2)	C12—C13—C14—Br1	177.56 (18)
C4—C5—C6—C1	1.9 (4)	C13—C14—C15—C16	0.8 (5)
C4—C5—C6—C8	178.6 (2)	Br1—C14—C15—C16	−178.2 (2)
N2—N1—C8—O2	−179.5 (2)	C14—C15—C16—C17	0.7 (4)
N2—N1—C8—C6	2.5 (4)	C11—N3—C17—C16	178.6 (3)
C1—C6—C8—O2	126.2 (3)	C11—N3—C17—C12	−1.7 (3)
C5—C6—C8—O2	−50.3 (3)	C15—C16—C17—N3	178.1 (3)
C1—C6—C8—N1	−55.8 (4)	C15—C16—C17—C12	−1.6 (4)
C5—C6—C8—N1	127.6 (3)	C13—C12—C17—N3	−178.8 (2)
N1—N2—C9—C10	−178.0 (3)	C10—C12—C17—N3	1.4 (3)
N2—C9—C10—C11	−168.6 (3)	C13—C12—C17—C16	1.0 (4)
N2—C9—C10—C12	12.3 (5)	C10—C12—C17—C16	−178.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O2^i	0.87 (2)	2.15 (2)	3.010 (3)	170 (3)
N3—H3n···O2^ii	0.85 (2)	2.13 (2)	2.976 (3)	169 (3)

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