2′-(1H-Indol-3-ylmethyl­ene)benzene­sulfonohydrazide

Ali, H.M.; Yusnita, J.; Wan Jefrey, B.; Ng, S.W.

doi:10.1107/S1600536807009518

2′-(1H-Indol-3-ylmethylene)benzenesulfonohydrazide

H. M. Ali, J. Yusnita, B. Wan Jefrey and S. W. Ng

The molecules of of the title compound, C₁₅H₁₃N₃O₂S, are linked by N_amino—H

O_sulfonyl and N_indolyl—H

N_imino hydrogen bonds into a layer.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807009518/hb2309sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807009518/hb2309Isup2.hkl Contains datablock I

CCDC reference: 643005

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R factor = 0.025
wR factor = 0.074
Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
            identifier.
            Faint

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.50
           From the CIF: _reflns_number_total               3256
           Count of symmetry unique reflns         1741
           Completeness (_total/calc)            187.02%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1515
           Fraction of Friedel pairs measured     0.870
           Are heavy atom types Z>Si present        yes

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

   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

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'-(1H-Indol-3-ylmethylene)benzenesulfonohydrazide top

Crystal data top

C₁₅H₁₃N₃O₂S	F(000) = 624
M_r = 299.34	D_x = 1.396 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 5770 reflections
a = 15.9617 (3) Å	θ = 2.1–34.3°
b = 9.5265 (2) Å	µ = 0.24 mm⁻¹
c = 9.3697 (2) Å	T = 173 K
V = 1424.75 (5) Å³	Block, faint yellow
Z = 4	0.50 × 0.24 × 0.24 mm

Data collection top

Bruker APEXII diffractometer	3256 independent reflections
Radiation source: medium-focus sealed tube	3183 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
φ and ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→20
T_min = 0.816, T_max = 0.946	k = −12→12
12134 measured reflections	l = −12→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.025	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.074	w = 1/[σ²(F_o²) + (0.0533P)² + 0.1391P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
3256 reflections	Δρ_max = 0.26 e Å⁻³
198 parameters	Δρ_min = −0.24 e Å⁻³
3 restraints	Absolute structure: Flack (1983), 1517 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (5)

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.794841 (15)	0.59999 (3)	0.50000 (3)	0.01731 (9)
O1	0.82604 (6)	0.66410 (11)	0.37143 (10)	0.0259 (2)
O2	0.71381 (5)	0.53418 (10)	0.49768 (13)	0.02458 (19)
N1	1.03122 (7)	1.02907 (13)	0.96877 (12)	0.0242 (3)
H1N	1.0492 (11)	1.0942 (15)	1.0216 (18)	0.028 (4)*
N2	0.86493 (6)	0.77689 (11)	0.66348 (12)	0.0178 (2)
N3	0.78616 (6)	0.72470 (12)	0.62158 (12)	0.0185 (2)
H3N	0.7509 (11)	0.7003 (19)	0.6860 (18)	0.034 (5)*
C1	0.87148 (7)	0.48342 (12)	0.56371 (14)	0.0180 (2)
C2	0.85550 (9)	0.41101 (14)	0.68954 (16)	0.0236 (3)
H2	0.8037	0.4222	0.7381	0.028*
C3	0.91692 (10)	0.32175 (16)	0.74303 (17)	0.0314 (3)
H3	0.9067	0.2702	0.8280	0.038*
C4	0.99289 (9)	0.30771 (16)	0.6729 (2)	0.0326 (3)
H4	1.0345	0.2464	0.7101	0.039*
C5	1.00858 (9)	0.38243 (15)	0.54905 (19)	0.0315 (3)
H5	1.0612	0.3734	0.5024	0.038*
C6	0.94742 (8)	0.47102 (13)	0.49242 (17)	0.0249 (3)
H6	0.9575	0.5218	0.4069	0.030*
C7	0.86688 (8)	0.83770 (13)	0.78553 (14)	0.0189 (2)
H7	0.8171	0.8453	0.8405	0.023*
C8	0.94934 (8)	0.99354 (14)	0.94633 (15)	0.0223 (3)
H8	0.9029	1.0314	0.9967	0.027*
C9	0.94426 (8)	0.89463 (12)	0.83970 (14)	0.0188 (2)
C10	1.02890 (8)	0.86306 (13)	0.79651 (14)	0.0181 (2)
C11	1.06579 (8)	0.76598 (13)	0.70294 (14)	0.0213 (3)
H11	1.0321	0.7028	0.6494	0.026*
C12	1.15228 (9)	0.76409 (15)	0.69025 (17)	0.0282 (3)
H12	1.1779	0.7001	0.6259	0.034*
C13	1.20261 (8)	0.85529 (17)	0.7711 (2)	0.0337 (4)
H13	1.2617	0.8524	0.7594	0.040*
C14	1.16827 (9)	0.94908 (16)	0.86726 (18)	0.0306 (3)
H14	1.2024	1.0098	0.9228	0.037*
C15	1.08119 (8)	0.95049 (13)	0.87898 (15)	0.0221 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01470 (14)	0.02269 (14)	0.01454 (14)	−0.00186 (9)	−0.00156 (11)	−0.00021 (12)
O1	0.0262 (5)	0.0349 (5)	0.0167 (4)	−0.0013 (4)	−0.0003 (4)	0.0040 (4)
O2	0.0163 (4)	0.0296 (4)	0.0278 (5)	−0.0046 (3)	−0.0061 (4)	−0.0027 (5)
N1	0.0235 (5)	0.0236 (5)	0.0256 (7)	−0.0026 (4)	−0.0019 (4)	−0.0092 (4)
N2	0.0155 (4)	0.0178 (5)	0.0202 (5)	−0.0023 (4)	−0.0018 (4)	0.0021 (4)
N3	0.0147 (5)	0.0218 (5)	0.0190 (5)	−0.0014 (4)	0.0012 (4)	−0.0014 (4)
C1	0.0147 (5)	0.0203 (5)	0.0191 (6)	−0.0004 (4)	−0.0025 (4)	−0.0033 (5)
C2	0.0209 (6)	0.0274 (6)	0.0224 (6)	−0.0006 (5)	−0.0018 (5)	0.0004 (5)
C3	0.0340 (8)	0.0298 (7)	0.0304 (8)	0.0014 (6)	−0.0107 (6)	0.0039 (6)
C4	0.0275 (7)	0.0263 (7)	0.0440 (9)	0.0060 (5)	−0.0148 (6)	−0.0098 (7)
C5	0.0189 (6)	0.0302 (7)	0.0454 (9)	0.0022 (5)	0.0012 (6)	−0.0157 (6)
C6	0.0208 (5)	0.0271 (6)	0.0270 (6)	−0.0024 (5)	0.0038 (6)	−0.0070 (6)
C7	0.0183 (5)	0.0183 (5)	0.0202 (6)	0.0011 (4)	0.0018 (5)	0.0004 (4)
C8	0.0220 (6)	0.0223 (6)	0.0226 (6)	−0.0006 (5)	0.0001 (5)	−0.0031 (5)
C9	0.0196 (6)	0.0182 (5)	0.0185 (6)	−0.0010 (4)	0.0004 (5)	−0.0002 (4)
C10	0.0196 (6)	0.0167 (5)	0.0182 (6)	−0.0002 (4)	−0.0009 (4)	0.0019 (5)
C11	0.0253 (6)	0.0181 (5)	0.0206 (6)	0.0021 (5)	−0.0011 (5)	−0.0008 (5)
C12	0.0259 (6)	0.0262 (6)	0.0324 (7)	0.0070 (5)	0.0023 (6)	−0.0027 (6)
C13	0.0198 (7)	0.0352 (8)	0.0460 (10)	0.0022 (5)	0.0006 (6)	−0.0042 (7)
C14	0.0218 (6)	0.0297 (7)	0.0403 (8)	−0.0031 (5)	−0.0023 (6)	−0.0070 (6)
C15	0.0230 (6)	0.0199 (6)	0.0234 (6)	−0.0012 (5)	−0.0015 (5)	−0.0022 (5)

Geometric parameters (Å, º) top

S1—O2	1.4375 (8)	C5—C6	1.395 (2)
S1—O1	1.4395 (10)	C5—H5	0.9500
S1—N3	1.6518 (11)	C6—H6	0.9500
S1—C1	1.7567 (12)	C7—C9	1.4413 (17)
N1—C8	1.3663 (17)	C7—H7	0.9500
N1—C15	1.3800 (17)	C8—C9	1.3757 (18)
N1—H1n	0.84 (1)	C8—H8	0.9500
N2—C7	1.2823 (17)	C9—C10	1.4420 (17)
N2—N3	1.4079 (14)	C10—C11	1.4038 (18)
N3—H3n	0.86 (1)	C10—C15	1.4097 (17)
C1—C6	1.3891 (17)	C11—C12	1.3858 (19)
C1—C2	1.3895 (19)	C11—H11	0.9500
C2—C3	1.391 (2)	C12—C13	1.405 (2)
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.386 (2)	C13—C14	1.382 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.384 (3)	C14—C15	1.3944 (19)
C4—H4	0.9500	C14—H14	0.9500

O2—S1—O1	118.92 (6)	C1—C6—H6	120.7
O2—S1—N3	104.40 (6)	C5—C6—H6	120.7
O1—S1—N3	107.52 (6)	N2—C7—C9	120.32 (12)
O2—S1—C1	110.85 (6)	N2—C7—H7	119.8
O1—S1—C1	108.16 (6)	C9—C7—H7	119.8
N3—S1—C1	106.19 (6)	N1—C8—C9	109.74 (12)
C8—N1—C15	108.94 (11)	N1—C8—H8	125.1
C8—N1—H1N	126.7 (12)	C9—C8—H8	125.1
C15—N1—H1N	124.0 (13)	C8—C9—C7	124.33 (12)
C7—N2—N3	115.46 (11)	C8—C9—C10	106.95 (12)
N2—N3—S1	111.80 (8)	C7—C9—C10	128.72 (11)
N2—N3—H3N	119.1 (14)	C11—C10—C15	118.90 (11)
S1—N3—H3N	110.2 (13)	C11—C10—C9	134.88 (12)
C6—C1—C2	121.73 (12)	C15—C10—C9	106.11 (11)
C6—C1—S1	119.87 (10)	C12—C11—C10	118.68 (12)
C2—C1—S1	118.32 (10)	C12—C11—H11	120.7
C1—C2—C3	118.67 (13)	C10—C11—H11	120.7
C1—C2—H2	120.7	C11—C12—C13	121.02 (13)
C3—C2—H2	120.7	C11—C12—H12	119.5
C4—C3—C2	120.33 (15)	C13—C12—H12	119.5
C4—C3—H3	119.8	C14—C13—C12	121.63 (13)
C2—C3—H3	119.8	C14—C13—H13	119.2
C5—C4—C3	120.41 (13)	C12—C13—H13	119.2
C5—C4—H4	119.8	C13—C14—C15	116.92 (13)
C3—C4—H4	119.8	C13—C14—H14	121.5
C4—C5—C6	120.21 (14)	C15—C14—H14	121.5
C4—C5—H5	119.9	N1—C15—C14	129.00 (13)
C6—C5—H5	119.9	N1—C15—C10	108.21 (11)
C1—C6—C5	118.63 (15)	C14—C15—C10	122.77 (13)

C7—N2—N3—S1	−158.19 (9)	N1—C8—C9—C10	2.10 (15)
O2—S1—N3—N2	165.18 (8)	N2—C7—C9—C8	160.94 (13)
O1—S1—N3—N2	−67.61 (10)	N2—C7—C9—C10	−18.8 (2)
C1—S1—N3—N2	47.98 (10)	C8—C9—C10—C11	174.26 (14)
O2—S1—C1—C6	134.06 (10)	C7—C9—C10—C11	−6.0 (2)
O1—S1—C1—C6	2.02 (12)	C8—C9—C10—C15	−1.82 (14)
N3—S1—C1—C6	−113.14 (11)	C7—C9—C10—C15	177.95 (13)
O2—S1—C1—C2	−49.19 (12)	C15—C10—C11—C12	−2.9 (2)
O1—S1—C1—C2	178.78 (10)	C9—C10—C11—C12	−178.61 (14)
N3—S1—C1—C2	63.62 (11)	C10—C11—C12—C13	1.2 (2)
C6—C1—C2—C3	−1.37 (19)	C11—C12—C13—C14	0.7 (3)
S1—C1—C2—C3	−178.06 (10)	C12—C13—C14—C15	−0.9 (2)
C1—C2—C3—C4	1.1 (2)	C8—N1—C15—C14	−178.31 (15)
C2—C3—C4—C5	0.1 (2)	C8—N1—C15—C10	0.37 (15)
C3—C4—C5—C6	−1.0 (2)	C13—C14—C15—N1	177.58 (15)
C2—C1—C6—C5	0.47 (19)	C13—C14—C15—C10	−0.9 (2)
S1—C1—C6—C5	177.11 (10)	C11—C10—C15—N1	−175.93 (12)
C4—C5—C6—C1	0.7 (2)	C9—C10—C15—N1	0.90 (15)
N3—N2—C7—C9	179.72 (10)	C11—C10—C15—C14	2.8 (2)
C15—N1—C8—C9	−1.57 (15)	C9—C10—C15—C14	179.68 (14)
N1—C8—C9—C7	−177.68 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···N2ⁱ	0.84 (1)	2.27 (1)	3.081 (2)	161 (2)
N3—H3n···O1ⁱⁱ	0.86 (1)	2.16 (1)	3.004 (2)	170 (2)

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

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2′-(1H-Indol-3-ylmethyl­ene)benzene­sulfonohydrazide

Supporting information

Key indicators

checkCIF/PLATON results

2′-(1H-Indol-3-ylmethylene)benzenesulfonohydrazide