2′-(2-Methyl-1H-indol-3-ylmethyl­ene)benzene­sulfonohydrazide

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

doi:10.1107/S1600536807033740

2′-(2-Methyl-1H-indol-3-ylmethylene)benzenesulfonohydrazide

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

The molecules of the title compound, C₁₆H₁₅N₃O₂S, are linked by an N—H(indolyl)

O(sulfonyl) hydrogen bond into a linear chain that runs along the a axis. A weak N—H(hydrazidyl)

O(sulfonyl) hydrogen bond links the chains into a layer.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033740/hb2478sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033740/hb2478Isup2.hkl Contains datablock I

CCDC reference: 657778

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.006 Å
R factor = 0.071
wR factor = 0.213
Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.20 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........    H1<I>N<
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........    H3<I>N<
PLAT731_ALERT_1_C Bond    Calc     0.88(3), Rep   0.882(10) ......       3.00 su-Ra
              N1   -H1N     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.88(3), Rep   0.880(10) ......       3.00 su-Ra
              N3   -H3N     1.555   1.555

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2

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

   4 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
   3 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

Comment top

Th structure of (1H-indole-3-methylene)benzenesulfonohydrazide consists of molecules that are hydrogen bonded into a layer motif; both the indolyl and amino groups are engaged in hydrogen bonding interactions (Ali et al., 2007). With the methyl-substituted title compound, the latter interaction is significantly weakened, so that the compound adopts only a chain structure. Adjacent molecules are linked into a chain that runs along the a axis of the unit cell.

Related literature top

For (1H-indole-3-methylene)benzenesulfonohydrazide, see Ali et al. (2007).

Experimental top

Benzenesulfohydrazine (0.30 g, 1.7 mmol) and 2-methylindole-3-carboxaldehyde (0.28 g, 1.7 mmol) were dissolved in ethanol (50 ml). The reactants were heated under reflux for 1 h. Slow evaporation of the solvent gve the Schiff base.

Structure description top

For (1H-indole-3-methylene)benzenesulfonohydrazide, see Ali et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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: publCIF (Westrip, 2007).

Figures top

Fig. 1. Thermal ellipsoid plot of C₁₆H₁₅N₃O₂S. Displacement ellipsoids are drawn at the 70% probability level, and H atoms are shown as spheres of arbitrary radii. The dashed lines denote hydrogen bonds.

2'-(2-Methyl-1H-indol-3-ylmethylene)benzenesulfonohydrazide top

Crystal data top

C₁₆H₁₅N₃O₂S	F(000) = 656
M_r = 313.37	D_x = 1.437 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8732 reflections
a = 11.1512 (11) Å	θ = 2.8–30.6°
b = 19.243 (2) Å	µ = 0.24 mm⁻¹
c = 6.9905 (8) Å	T = 173 K
β = 105.076 (6)°	Block, yellow
V = 1448.4 (3) Å³	0.45 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	1919 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tube	R_int = 0.087
Graphite monochromator	θ_max = 26.0°, θ_min = 1.9°
φ and ω scans	h = −13→13
8053 measured reflections	k = −22→23
2829 independent reflections	l = −6→8

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.213	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ²(F_o²) + (0.0886P)²] where P = (F_o² + 2F_c²)/3
2829 reflections	(Δ/σ)_max = 0.001
208 parameters	Δρ_max = 0.51 e Å⁻³
2 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

C₁₆H₁₅N₃O₂S	V = 1448.4 (3) Å³
M_r = 313.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.1512 (11) Å	µ = 0.24 mm⁻¹
b = 19.243 (2) Å	T = 173 K
c = 6.9905 (8) Å	0.45 × 0.20 × 0.20 mm
β = 105.076 (6)°

Data collection top

Bruker APEXII diffractometer	1919 reflections with I > 2σ(I)
8053 measured reflections	R_int = 0.087
2829 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	2 restraints
wR(F²) = 0.213	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	Δρ_max = 0.51 e Å⁻³
2829 reflections	Δρ_min = −0.63 e Å⁻³
208 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.98807 (9)	0.33779 (5)	0.84350 (13)	0.0201 (3)
O1	1.1071 (3)	0.32097 (13)	0.9723 (4)	0.0256 (7)
O2	0.9785 (3)	0.35803 (14)	0.6438 (4)	0.0246 (7)
N1	0.3755 (3)	0.19967 (16)	0.5410 (4)	0.0211 (7)
H1N	0.309 (2)	0.1732 (16)	0.512 (5)	0.015 (10)*
N2	0.7768 (3)	0.28039 (16)	0.7403 (4)	0.0208 (7)
N3	0.9041 (3)	0.26672 (16)	0.8314 (5)	0.0208 (7)
H3N	0.922 (5)	0.245 (2)	0.946 (4)	0.048 (15)*
C1	0.3744 (4)	0.27162 (19)	0.5421 (5)	0.0200 (8)
C2	0.2749 (4)	0.3174 (2)	0.4925 (5)	0.0242 (9)
H2	0.1919	0.3013	0.4461	0.029*
C3	0.3024 (4)	0.3875 (2)	0.5139 (5)	0.0251 (9)
H3	0.2366	0.4203	0.4820	0.030*
C4	0.4239 (4)	0.41119 (19)	0.5809 (5)	0.0243 (9)
H4	0.4393	0.4598	0.5935	0.029*
C5	0.5229 (4)	0.3655 (2)	0.6297 (5)	0.0224 (9)
H5	0.6056	0.3822	0.6760	0.027*
C6	0.4987 (4)	0.29412 (19)	0.6094 (5)	0.0181 (8)
C7	0.5742 (4)	0.23212 (19)	0.6511 (5)	0.0180 (8)
C8	0.4946 (4)	0.17566 (19)	0.6077 (5)	0.0191 (8)
C9	0.5214 (4)	0.09976 (19)	0.6243 (5)	0.0245 (9)
H9A	0.4819	0.0770	0.4982	0.037*
H9B	0.4886	0.0800	0.7296	0.037*
H9C	0.6114	0.0923	0.6560	0.037*
C10	0.7056 (4)	0.22701 (18)	0.7316 (5)	0.0191 (8)
H10	0.7412	0.1835	0.7796	0.023*
C11	0.9191 (4)	0.40312 (18)	0.9554 (5)	0.0201 (8)
C12	0.8402 (4)	0.45112 (19)	0.8375 (5)	0.0218 (9)
H12	0.8226	0.4485	0.6973	0.026*
C13	0.7874 (4)	0.5029 (2)	0.9274 (6)	0.0269 (9)
H13	0.7347	0.5366	0.8485	0.032*
C14	0.8115 (4)	0.5055 (2)	1.1316 (6)	0.0260 (9)
H14	0.7748	0.5409	1.1925	0.031*
C15	0.8889 (4)	0.4566 (2)	1.2477 (5)	0.0255 (9)
H15	0.9046	0.4585	1.3879	0.031*
C16	0.9433 (4)	0.4051 (2)	1.1601 (5)	0.0239 (9)
H16	0.9965	0.3716	1.2393	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0182 (6)	0.0181 (5)	0.0225 (5)	0.0006 (4)	0.0025 (4)	−0.0002 (3)
O1	0.0181 (16)	0.0220 (14)	0.0315 (15)	0.0037 (11)	−0.0026 (11)	0.0006 (11)
O2	0.0247 (17)	0.0251 (15)	0.0251 (15)	0.0011 (12)	0.0082 (12)	0.0005 (11)
N1	0.0191 (19)	0.0176 (17)	0.0244 (17)	−0.0020 (14)	0.0014 (13)	−0.0016 (12)
N2	0.0173 (18)	0.0208 (17)	0.0214 (16)	0.0006 (13)	0.0000 (13)	0.0017 (12)
N3	0.0177 (19)	0.0160 (16)	0.0253 (18)	0.0002 (13)	−0.0003 (14)	0.0013 (13)
C1	0.023 (2)	0.0186 (19)	0.0170 (18)	−0.0024 (16)	0.0030 (15)	−0.0018 (14)
C2	0.022 (2)	0.026 (2)	0.024 (2)	−0.0005 (17)	0.0039 (16)	0.0009 (15)
C3	0.030 (3)	0.022 (2)	0.021 (2)	0.0070 (17)	0.0038 (16)	0.0026 (15)
C4	0.034 (3)	0.0165 (19)	0.022 (2)	0.0002 (17)	0.0076 (17)	−0.0017 (15)
C5	0.028 (2)	0.0205 (19)	0.0177 (19)	−0.0041 (17)	0.0037 (15)	−0.0020 (14)
C6	0.021 (2)	0.021 (2)	0.0113 (17)	−0.0015 (16)	0.0031 (14)	−0.0006 (14)
C7	0.019 (2)	0.0214 (19)	0.0132 (17)	−0.0006 (16)	0.0036 (14)	−0.0011 (13)
C8	0.024 (2)	0.0185 (18)	0.0150 (17)	−0.0004 (16)	0.0050 (15)	−0.0012 (14)
C9	0.028 (2)	0.018 (2)	0.026 (2)	−0.0009 (17)	0.0040 (16)	−0.0001 (15)
C10	0.024 (2)	0.0175 (19)	0.0154 (18)	0.0009 (15)	0.0037 (15)	−0.0006 (14)
C11	0.020 (2)	0.0163 (19)	0.025 (2)	−0.0025 (15)	0.0075 (15)	−0.0007 (14)
C12	0.023 (2)	0.020 (2)	0.021 (2)	0.0007 (16)	0.0043 (16)	0.0042 (14)
C13	0.026 (2)	0.022 (2)	0.033 (2)	0.0033 (17)	0.0080 (17)	0.0038 (16)
C14	0.030 (2)	0.019 (2)	0.032 (2)	−0.0022 (17)	0.0128 (17)	−0.0038 (16)
C15	0.035 (3)	0.024 (2)	0.0182 (19)	−0.0049 (18)	0.0079 (17)	−0.0021 (15)
C16	0.022 (2)	0.022 (2)	0.027 (2)	−0.0028 (16)	0.0048 (16)	0.0020 (15)

Geometric parameters (Å, º) top

S1—O2	1.426 (3)	C6—C7	1.445 (5)
S1—O1	1.433 (3)	C7—C8	1.386 (5)
S1—N3	1.647 (3)	C7—C10	1.430 (5)
S1—C11	1.759 (4)	C8—C9	1.489 (5)
N1—C8	1.368 (5)	C9—H9A	0.9800
N1—C1	1.385 (5)	C9—H9B	0.9800
N1—H1N	0.882 (10)	C9—H9C	0.9800
N2—C10	1.290 (5)	C10—H10	0.9500
N2—N3	1.422 (4)	C11—C16	1.386 (5)
N3—H3N	0.880 (10)	C11—C12	1.389 (5)
C1—C2	1.388 (5)	C12—C13	1.388 (5)
C1—C6	1.411 (5)	C12—H12	0.9500
C2—C3	1.383 (5)	C13—C14	1.383 (5)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.390 (6)	C14—C15	1.387 (6)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.382 (6)	C15—C16	1.385 (5)
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.401 (5)	C16—H16	0.9500
C5—H5	0.9500

O2—S1—O1	119.85 (18)	C8—C7—C6	107.3 (3)
O2—S1—N3	106.27 (16)	C10—C7—C6	128.3 (3)
O1—S1—N3	105.40 (16)	N1—C8—C7	108.6 (3)
O2—S1—C11	108.05 (17)	N1—C8—C9	121.0 (3)
O1—S1—C11	108.79 (17)	C7—C8—C9	130.4 (4)
N3—S1—C11	107.93 (18)	C8—C9—H9A	109.5
C8—N1—C1	110.2 (3)	C8—C9—H9B	109.5
C8—N1—H1N	125 (3)	H9A—C9—H9B	109.5
C1—N1—H1N	125 (3)	C8—C9—H9C	109.5
C10—N2—N3	113.8 (3)	H9A—C9—H9C	109.5
N2—N3—S1	110.9 (2)	H9B—C9—H9C	109.5
N2—N3—H3N	117 (4)	N2—C10—C7	121.2 (3)
S1—N3—H3N	111 (3)	N2—C10—H10	119.4
N1—C1—C2	129.8 (4)	C7—C10—H10	119.4
N1—C1—C6	107.4 (3)	C16—C11—C12	121.2 (4)
C2—C1—C6	122.7 (3)	C16—C11—S1	119.2 (3)
C3—C2—C1	116.8 (4)	C12—C11—S1	119.6 (3)
C3—C2—H2	121.6	C13—C12—C11	119.1 (3)
C1—C2—H2	121.6	C13—C12—H12	120.4
C2—C3—C4	121.7 (4)	C11—C12—H12	120.4
C2—C3—H3	119.1	C14—C13—C12	120.1 (4)
C4—C3—H3	119.1	C14—C13—H13	119.9
C5—C4—C3	121.3 (4)	C12—C13—H13	119.9
C5—C4—H4	119.3	C13—C14—C15	120.2 (4)
C3—C4—H4	119.3	C13—C14—H14	119.9
C4—C5—C6	118.6 (4)	C15—C14—H14	119.9
C4—C5—H5	120.7	C16—C15—C14	120.3 (3)
C6—C5—H5	120.7	C16—C15—H15	119.9
C5—C6—C1	118.8 (4)	C14—C15—H15	119.9
C5—C6—C7	134.7 (4)	C15—C16—C11	119.1 (4)
C1—C6—C7	106.5 (3)	C15—C16—H16	120.5
C8—C7—C10	124.4 (3)	C11—C16—H16	120.5

C10—N2—N3—S1	−178.1 (3)	C1—N1—C8—C9	179.0 (3)
O2—S1—N3—N2	−63.5 (3)	C10—C7—C8—N1	177.6 (3)
O1—S1—N3—N2	168.4 (2)	C6—C7—C8—N1	0.4 (4)
C11—S1—N3—N2	52.2 (3)	C10—C7—C8—C9	−2.3 (6)
C8—N1—C1—C2	−177.9 (4)	C6—C7—C8—C9	−179.5 (3)
C8—N1—C1—C6	1.0 (4)	N3—N2—C10—C7	177.7 (3)
N1—C1—C2—C3	178.1 (3)	C8—C7—C10—N2	169.2 (3)
C6—C1—C2—C3	−0.7 (5)	C6—C7—C10—N2	−14.2 (6)
C1—C2—C3—C4	0.3 (5)	O2—S1—C11—C16	−163.7 (3)
C2—C3—C4—C5	−0.1 (6)	O1—S1—C11—C16	−32.1 (4)
C3—C4—C5—C6	0.3 (5)	N3—S1—C11—C16	81.7 (3)
C4—C5—C6—C1	−0.7 (5)	O2—S1—C11—C12	17.2 (4)
C4—C5—C6—C7	−177.1 (4)	O1—S1—C11—C12	148.8 (3)
N1—C1—C6—C5	−178.2 (3)	N3—S1—C11—C12	−97.3 (3)
C2—C1—C6—C5	0.9 (5)	C16—C11—C12—C13	1.6 (6)
N1—C1—C6—C7	−0.8 (4)	S1—C11—C12—C13	−179.3 (3)
C2—C1—C6—C7	178.3 (3)	C11—C12—C13—C14	−1.3 (6)
C5—C6—C7—C8	177.0 (4)	C12—C13—C14—C15	0.3 (6)
C1—C6—C7—C8	0.3 (4)	C13—C14—C15—C16	0.4 (6)
C5—C6—C7—C10	0.0 (7)	C14—C15—C16—C11	−0.1 (6)
C1—C6—C7—C10	−176.8 (3)	C12—C11—C16—C15	−0.9 (6)
C1—N1—C8—C7	−0.9 (4)	S1—C11—C16—C15	−180.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1ⁱ	0.88 (1)	2.20 (3)	2.933 (4)	141 (3)
N3—H3n···O2ⁱⁱ	0.88 (1)	2.40 (2)	3.206 (4)	152 (4)

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅N₃O₂S
M_r	313.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	11.1512 (11), 19.243 (2), 6.9905 (8)
β (°)	105.076 (6)
V (Å³)	1448.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.45 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8053, 2829, 1919
R_int	0.087
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.213, 1.15
No. of reflections	2829
No. of parameters	208
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.63

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).