5-Chloro-1H-indole-3-carbaldehyde 4-chlorobenzoyl­hydrazone

The amido O atom in the title mol­ecule, C₁₆H₁₁Cl₂N₃O, is the hydrogen-bond acceptor for the amide group and amine groups of two adjacent mol­ecules; the hydrogen-bonding inter­actions result in a layer motif.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.051
• wR factor = 0.155
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of Tmax/Tmin expected RT(exp) is > 1.10
            Absorption corrections should be applied.
            Tmin and Tmax expected:      0.813     0.905
            RT(exp) =      1.113
PLAT057_ALERT_3_C Correction for Absorption Required   RT(exp) ...       1.12
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C13    -   C14     ..       5.08 su

   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
   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
   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.

5-Chloro-1H-indole-3-carbaldehyde 4-chlorobenzoylhydrazone

Crystal data

C16H11Cl2N3O	F(000) = 680
Mr = 332.18	Dx = 1.465 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3416 reflections
a = 8.7172 (8) Å	θ = 2.5–24.5°
b = 8.6686 (8) Å	µ = 0.44 mm^−1
c = 19.960 (2) Å	T = 295 K
β = 93.202 (1)°	Irregular fragment, yellow
V = 1505.9 (2) Å^3	0.49 × 0.47 × 0.23 mm
Z = 4

Data collection

Bruker APEX-II area-detector diffractometer	2181 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
Graphite monochromator	θmax = 27.5°, θmin = 2.0°
φ and ω scans	h = −11→10
13557 measured reflections	k = −11→11
3423 independent reflections	l = −25→25

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0675P)^2 + 0.7475P] where P = (Fo^2 + 2Fc^2)/3
3423 reflections	(Δ/σ)max = 0.001
207 parameters	Δρmax = 0.46 e Å^−3
2 restraints	Δρmin = −0.63 e Å^−3

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

	x	y	z	Uiso*/Ueq
Cl1	0.10014 (11)	−0.33525 (10)	0.52693 (4)	0.0853 (3)
Cl2	0.34286 (13)	−0.30193 (11)	0.69859 (8)	0.1215 (5)
O1	0.3703 (2)	0.3651 (2)	0.45289 (8)	0.0683 (6)
N1	0.4325 (3)	0.3636 (2)	0.56324 (9)	0.0536 (6)
H1n	0.477 (3)	0.4505 (19)	0.5581 (14)	0.064 (8)*
N2	0.4598 (2)	0.2768 (2)	0.62142 (9)	0.0478 (5)
N3	0.6699 (3)	0.2077 (4)	0.83407 (11)	0.0739 (8)
H3n	0.719 (4)	0.212 (4)	0.8720 (10)	0.109 (13)*
C1	0.2964 (3)	0.1425 (3)	0.51291 (11)	0.0467 (6)
C2	0.3214 (3)	0.0337 (3)	0.46364 (12)	0.0556 (7)
H2	0.3799	0.0597	0.4277	0.067*
C3	0.2602 (3)	−0.1125 (3)	0.46754 (13)	0.0595 (7)
H3	0.2782	−0.1853	0.4347	0.071*
C4	0.1724 (3)	−0.1499 (3)	0.52033 (13)	0.0562 (7)
C5	0.1416 (3)	−0.0423 (3)	0.56857 (13)	0.0586 (7)
H5	0.0794	−0.0675	0.6033	0.070*
C6	0.2042 (3)	0.1033 (3)	0.56461 (12)	0.0530 (6)
H6	0.1842	0.1762	0.5972	0.064*
C7	0.3683 (3)	0.2975 (3)	0.50756 (11)	0.0518 (6)
C8	0.5310 (3)	0.3459 (3)	0.67027 (11)	0.0477 (6)
H8	0.5584	0.4490	0.6664	0.057*
C9	0.5682 (3)	0.2629 (3)	0.73131 (10)	0.0479 (6)
C10	0.6527 (3)	0.3190 (4)	0.78671 (12)	0.0618 (7)
H10	0.6919	0.4185	0.7908	0.074*
C11	0.5994 (3)	0.0760 (4)	0.81107 (12)	0.0648 (8)
C12	0.5856 (5)	−0.0678 (5)	0.84100 (17)	0.0917 (12)
H12	0.6275	−0.0857	0.8842	0.110*
C13	0.5095 (5)	−0.1824 (5)	0.8058 (2)	0.0976 (13)
H13	0.5016	−0.2800	0.8247	0.117*
C14	0.4434 (4)	−0.1534 (4)	0.74153 (18)	0.0771 (9)
C15	0.4536 (3)	−0.0125 (3)	0.71096 (14)	0.0586 (7)
H15	0.4087	0.0046	0.6682	0.070*
C16	0.5336 (3)	0.1048 (3)	0.74591 (11)	0.0503 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1104 (7)	0.0644 (5)	0.0805 (6)	−0.0241 (4)	−0.0011 (5)	−0.0131 (4)
Cl2	0.1040 (8)	0.0555 (5)	0.2073 (14)	−0.0108 (5)	0.0305 (8)	0.0093 (6)
O1	0.0968 (14)	0.0729 (12)	0.0325 (8)	−0.0167 (11)	−0.0200 (9)	0.0119 (8)
N1	0.0785 (15)	0.0476 (12)	0.0327 (10)	−0.0082 (11)	−0.0141 (9)	0.0079 (9)
N2	0.0610 (12)	0.0500 (11)	0.0308 (9)	−0.0044 (9)	−0.0095 (8)	0.0045 (8)
N3	0.0828 (18)	0.108 (2)	0.0296 (11)	0.0145 (16)	−0.0107 (11)	0.0052 (13)
C1	0.0522 (13)	0.0534 (14)	0.0332 (11)	0.0022 (11)	−0.0099 (10)	−0.0020 (10)
C2	0.0629 (16)	0.0686 (17)	0.0345 (12)	−0.0028 (13)	−0.0032 (11)	−0.0059 (11)
C3	0.0646 (16)	0.0644 (17)	0.0485 (14)	0.0034 (14)	−0.0052 (12)	−0.0179 (12)
C4	0.0586 (15)	0.0575 (16)	0.0511 (14)	−0.0049 (12)	−0.0083 (12)	−0.0103 (12)
C5	0.0604 (16)	0.0675 (17)	0.0480 (13)	−0.0118 (13)	0.0043 (11)	−0.0097 (13)
C6	0.0545 (14)	0.0609 (16)	0.0432 (13)	−0.0005 (12)	−0.0015 (11)	−0.0126 (11)
C7	0.0627 (15)	0.0569 (15)	0.0341 (11)	0.0004 (12)	−0.0119 (10)	0.0011 (11)
C8	0.0604 (15)	0.0492 (13)	0.0324 (11)	−0.0041 (11)	−0.0068 (10)	0.0026 (10)
C9	0.0526 (14)	0.0605 (15)	0.0298 (10)	−0.0016 (11)	−0.0035 (9)	0.0020 (10)
C10	0.0680 (17)	0.081 (2)	0.0354 (12)	−0.0027 (14)	−0.0073 (11)	−0.0017 (12)
C11	0.0711 (18)	0.087 (2)	0.0368 (12)	0.0231 (16)	0.0069 (12)	0.0182 (14)
C12	0.106 (3)	0.112 (3)	0.0594 (19)	0.045 (2)	0.0286 (18)	0.046 (2)
C13	0.111 (3)	0.079 (2)	0.108 (3)	0.029 (2)	0.054 (2)	0.049 (2)
C14	0.073 (2)	0.0605 (18)	0.101 (2)	0.0098 (15)	0.0285 (18)	0.0229 (17)
C15	0.0555 (15)	0.0561 (15)	0.0644 (16)	0.0036 (13)	0.0068 (12)	0.0121 (13)
C16	0.0522 (14)	0.0615 (15)	0.0373 (11)	0.0096 (12)	0.0033 (10)	0.0105 (11)

Geometric parameters (Å, º)

Cl1—C4	1.733 (3)	C5—C6	1.378 (4)
Cl2—C14	1.754 (4)	C5—H5	0.9300
O1—C7	1.240 (3)	C6—H6	0.9300
N1—C7	1.344 (3)	C8—C9	1.436 (3)
N1—N2	1.393 (3)	C8—H8	0.9300
N1—H1n	0.86 (1)	C9—C10	1.382 (3)
N2—C8	1.275 (3)	C9—C16	1.437 (4)
N3—C10	1.353 (4)	C10—H10	0.9300
N3—C11	1.364 (4)	C11—C12	1.390 (5)
N3—H3n	0.85 (1)	C11—C16	1.414 (3)
C1—C6	1.385 (3)	C12—C13	1.367 (6)
C1—C2	1.388 (3)	C12—H12	0.9300
C1—C7	1.489 (4)	C13—C14	1.400 (6)
C2—C3	1.379 (4)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.371 (4)
C3—C4	1.375 (4)	C15—C16	1.397 (4)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.378 (4)
C7—N1—N2	120.2 (2)	N2—C8—C9	119.4 (2)
C7—N1—H1n	116.6 (19)	N2—C8—H8	120.3
N2—N1—H1n	121.2 (19)	C9—C8—H8	120.3
C8—N2—N1	115.9 (2)	C10—C9—C8	126.0 (2)
C10—N3—C11	109.4 (2)	C10—C9—C16	106.4 (2)
C10—N3—H3n	128 (3)	C8—C9—C16	127.6 (2)
C11—N3—H3n	122 (3)	N3—C10—C9	110.0 (3)
C6—C1—C2	118.8 (2)	N3—C10—H10	125.0
C6—C1—C7	122.6 (2)	C9—C10—H10	125.0
C2—C1—C7	118.6 (2)	N3—C11—C12	130.8 (3)
C3—C2—C1	120.5 (2)	N3—C11—C16	108.3 (2)
C3—C2—H2	119.8	C12—C11—C16	120.9 (3)
C1—C2—H2	119.8	C13—C12—C11	118.8 (3)
C4—C3—C2	119.6 (2)	C13—C12—H12	120.6
C4—C3—H3	120.2	C11—C12—H12	120.6
C2—C3—H3	120.2	C12—C13—C14	120.2 (3)
C3—C4—C5	120.9 (3)	C12—C13—H13	119.9
C3—C4—Cl1	119.8 (2)	C14—C13—H13	119.9
C5—C4—Cl1	119.3 (2)	C15—C14—C13	122.3 (4)
C4—C5—C6	119.1 (3)	C15—C14—Cl2	118.7 (3)
C4—C5—H5	120.4	C13—C14—Cl2	119.0 (3)
C6—C5—H5	120.4	C14—C15—C16	118.0 (3)
C1—C6—C5	121.0 (2)	C14—C15—H15	121.0
C1—C6—H6	119.5	C16—C15—H15	121.0
C5—C6—H6	119.5	C15—C16—C11	119.8 (3)
O1—C7—N1	120.0 (2)	C15—C16—C9	134.2 (2)
O1—C7—C1	121.1 (2)	C11—C16—C9	106.0 (2)
N1—C7—C1	118.9 (2)
C7—N1—N2—C8	175.1 (2)	C8—C9—C10—N3	−177.9 (3)
C6—C1—C2—C3	−2.4 (4)	C16—C9—C10—N3	−0.9 (3)
C7—C1—C2—C3	178.4 (2)	C10—N3—C11—C12	180.0 (3)
C1—C2—C3—C4	0.7 (4)	C10—N3—C11—C16	−0.2 (3)
C2—C3—C4—C5	1.6 (4)	N3—C11—C12—C13	−179.0 (3)
C2—C3—C4—Cl1	−178.0 (2)	C16—C11—C12—C13	1.2 (5)
C3—C4—C5—C6	−2.1 (4)	C11—C12—C13—C14	−1.7 (5)
Cl1—C4—C5—C6	177.5 (2)	C12—C13—C14—C15	1.0 (5)
C2—C1—C6—C5	1.9 (4)	C12—C13—C14—Cl2	−178.6 (3)
C7—C1—C6—C5	−178.9 (2)	C13—C14—C15—C16	0.2 (4)
C4—C5—C6—C1	0.3 (4)	Cl2—C14—C15—C16	179.8 (2)
N2—N1—C7—O1	−166.4 (2)	C14—C15—C16—C11	−0.7 (4)
N2—N1—C7—C1	13.3 (4)	C14—C15—C16—C9	−179.9 (3)
C6—C1—C7—O1	−137.3 (3)	N3—C11—C16—C15	−179.8 (2)
C2—C1—C7—O1	41.9 (4)	C12—C11—C16—C15	0.0 (4)
C6—C1—C7—N1	43.0 (4)	N3—C11—C16—C9	−0.4 (3)
C2—C1—C7—N1	−137.8 (3)	C12—C11—C16—C9	179.5 (3)
N1—N2—C8—C9	−177.9 (2)	C10—C9—C16—C15	−179.9 (3)
N2—C8—C9—C10	175.8 (3)	C8—C9—C16—C15	−3.0 (5)
N2—C8—C9—C16	−0.5 (4)	C10—C9—C16—C11	0.8 (3)
C11—N3—C10—C9	0.7 (3)	C8—C9—C16—C11	177.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1^i	0.86 (1)	2.10 (1)	2.941 (3)	167 (3)
N3—H3n···O1^ii	0.85 (1)	2.13 (2)	2.935 (3)	157 (4)

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