{[(E)-(1,3-Benzodioxol-5-yl)methyl­idene]amino}thio­urea

The synthesis and crystallographic analysis of [(E)-1,3-benzodioxol-5-yl­methyl­idene­amino]­thio­urea is reported, offering a comprehensive exploration of its structural features and supra­mol­ecular arrangements within the crystal.

Computing details

{[(E)-(1,3-Benzodioxol-5-yl)methylidene]amino}thiourea

Crystal data

C9H9N3O2S	F(000) = 464
Mr = 223.26	Dx = 1.478 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3399 reflections
a = 7.1189 (2) Å	θ = 3.2–27.6°
b = 10.9687 (2) Å	µ = 0.31 mm^−1
c = 13.0678 (3) Å	T = 293 K
β = 100.426 (2)°	Tabular, colourless
V = 1003.55 (4) Å^3	0.58 × 0.34 × 0.17 mm
Z = 4

Data collection

Bruker APEXII diffractometer	2447 reflections with I > 2.0σ(I)
Graphite monochromator	Rint = 0.000
φ & ω scans	θmax = 33.2°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −10→10
Tmin = 0.88, Tmax = 0.95	k = −16→16
19600 measured reflections	l = −20→20
3818 independent reflections

Refinement

Refinement on F^2	Primary atom site location: other
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.104	Method = Modified Sheldrick w = 1/[σ^2(F^2) + ( 0.04P)^2 + 0.31P] , where P = (max(Fo^2,0) + 2Fc^2)/3
S = 0.95	(Δ/σ)max = 0.001
3810 reflections	Δρmax = 0.38 e Å^−3
148 parameters	Δρmin = −0.32 e Å^−3
10 restraints

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

	x	y	z	Uiso*/Ueq
N1	0.4666 (2)	0.28730 (12)	0.27357 (10)	0.0521
S2	0.41135 (7)	0.51407 (3)	0.33300 (3)	0.0508
C3	0.4856 (2)	0.36798 (11)	0.35054 (10)	0.0378
O4	0.82417 (18)	−0.24246 (9)	0.43350 (9)	0.0596
N5	0.62732 (16)	0.20875 (9)	0.45653 (9)	0.0383
C6	0.70095 (19)	0.17336 (12)	0.54832 (10)	0.0392
O7	0.96272 (18)	−0.30444 (10)	0.59886 (10)	0.0619
C8	0.76809 (19)	0.04823 (12)	0.56576 (10)	0.0370
C9	0.75307 (19)	−0.03330 (11)	0.48105 (10)	0.0375
C10	0.8517 (2)	0.01062 (15)	0.66540 (11)	0.0497
C11	0.9050 (2)	−0.18475 (13)	0.60146 (12)	0.0451
C12	0.82203 (19)	−0.14781 (12)	0.50257 (11)	0.0389
N13	0.56921 (18)	0.32877 (10)	0.44507 (9)	0.0405
C14	0.9020 (3)	−0.34471 (13)	0.49501 (14)	0.0556
C15	0.9220 (3)	−0.10782 (16)	0.68462 (12)	0.0560
H61	0.7130	0.2267	0.6055	0.0484*
H91	0.6977	−0.0091	0.4133	0.0462*
H101	0.8592	0.0663	0.7228	0.0604*
H141	1.0143	−0.3736	0.4670	0.0677*
H142	0.8011	−0.4081	0.4918	0.0665*
H151	0.9779	−0.1327	0.7520	0.0688*
H12	0.395 (3)	0.3055 (15)	0.2155 (12)	0.0633 (19)*
H131	0.577 (2)	0.3758 (12)	0.4987 (10)	0.0488 (18)*
H11	0.498 (3)	0.2137 (13)	0.2878 (12)	0.0632 (19)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0787 (10)	0.0371 (6)	0.0379 (6)	0.0057 (6)	0.0032 (6)	−0.0042 (5)
S2	0.0777 (3)	0.03268 (16)	0.04106 (19)	0.00766 (16)	0.00842 (17)	0.00264 (13)
C3	0.0442 (7)	0.0321 (6)	0.0381 (6)	−0.0018 (5)	0.0103 (5)	−0.0016 (5)
O4	0.0838 (9)	0.0308 (5)	0.0576 (7)	0.0074 (5)	−0.0046 (6)	0.0013 (4)
N5	0.0428 (6)	0.0299 (5)	0.0426 (6)	0.0028 (4)	0.0086 (5)	−0.0001 (4)
C6	0.0410 (7)	0.0381 (6)	0.0392 (7)	0.0004 (5)	0.0090 (5)	−0.0018 (5)
O7	0.0703 (8)	0.0422 (6)	0.0685 (8)	0.0094 (5)	−0.0002 (6)	0.0207 (5)
C8	0.0353 (6)	0.0380 (6)	0.0376 (6)	−0.0017 (5)	0.0067 (5)	0.0040 (5)
C9	0.0385 (7)	0.0346 (6)	0.0374 (6)	−0.0010 (5)	0.0009 (5)	0.0055 (5)
C10	0.0577 (9)	0.0547 (8)	0.0353 (7)	0.0021 (7)	0.0048 (6)	0.0027 (6)
C11	0.0417 (7)	0.0405 (7)	0.0517 (8)	0.0005 (6)	0.0045 (6)	0.0161 (6)
C12	0.0386 (7)	0.0334 (6)	0.0430 (7)	−0.0029 (5)	0.0027 (5)	0.0046 (5)
N13	0.0534 (7)	0.0310 (5)	0.0362 (6)	0.0055 (5)	0.0060 (5)	−0.0031 (4)
C14	0.0565 (9)	0.0339 (7)	0.0760 (11)	0.0052 (6)	0.0107 (8)	0.0129 (7)
C15	0.0631 (10)	0.0617 (10)	0.0390 (7)	0.0037 (8)	−0.0016 (7)	0.0164 (7)

Geometric parameters (Å, º)

N1—C3	1.3281 (17)	C8—C9	1.4120 (18)
N1—H12	0.858 (14)	C8—C10	1.3926 (19)
N1—H11	0.849 (14)	C9—C12	1.3592 (17)
S2—C3	1.6899 (13)	C9—H91	0.941
C3—N13	1.3414 (17)	C10—C15	1.399 (2)
O4—C12	1.3776 (17)	C10—H101	0.961
O4—C14	1.4318 (17)	C11—C12	1.3809 (19)
N5—C6	1.2793 (17)	C11—C15	1.364 (2)
N5—N13	1.3800 (15)	N13—H131	0.864 (13)
C6—C8	1.4576 (18)	C14—H141	0.990
C6—H61	0.941	C14—H142	0.995
O7—C11	1.3779 (18)	C15—H151	0.939
O7—C14	1.418 (2)
C3—N1—H12	118.5 (11)	C15—C10—H101	118.8
C3—N1—H11	118.8 (11)	O7—C11—C12	109.60 (14)
H12—N1—H11	120.3 (15)	O7—C11—C15	128.71 (13)
S2—C3—N1	122.87 (11)	C12—C11—C15	121.69 (13)
S2—C3—N13	120.31 (10)	C11—C12—O4	109.78 (12)
N1—C3—N13	116.82 (12)	C11—C12—C9	122.83 (13)
C12—O4—C14	105.76 (11)	O4—C12—C9	127.39 (12)
C6—N5—N13	117.07 (11)	N5—N13—C3	118.70 (11)
N5—C6—C8	119.96 (12)	N5—N13—H131	120.5 (9)
N5—C6—H61	121.3	C3—N13—H131	120.5 (9)
C8—C6—H61	118.7	O4—C14—O7	108.25 (12)
C11—O7—C14	106.25 (11)	O4—C14—H141	107.4
C6—C8—C9	119.84 (12)	O7—C14—H141	109.1
C6—C8—C10	119.85 (13)	O4—C14—H142	108.7
C9—C8—C10	120.28 (13)	O7—C14—H142	110.5
C8—C9—C12	116.73 (12)	H141—C14—H142	112.7
C8—C9—H91	121.3	C10—C15—C11	117.03 (13)
C12—C9—H91	122.0	C10—C15—H151	121.0
C8—C10—C15	121.44 (14)	C11—C15—H151	121.9
C8—C10—H101	119.7

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···N5	0.85 (2)	2.23 (2)	2.6034 (17)	107 (1)
N1—H11···S2^i	0.85 (2)	2.84 (2)	3.4805 (14)	134 (1)
N1—H12···O4^ii	0.86 (1)	2.32 (2)	3.112 (2)	153 (2)
N13—H131···S2^iii	0.86 (1)	2.50 (1)	3.3550 (12)	172 (1)

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