1-[(E)-(3-Hy­droxy-4-meth­oxy­benzyl­idene)amino]-3-methyl­thio­urea

In the title thio­semicarbazone Schiff base compound, C₁₀H₁₃N₃O₂S, the dihedral angle between the benzene ring and methyl carbo­thio­amide side arm was found to be 17.4 (4)°. The presence of two intra­molecular hydrogen bonds is noted, namely hy­droxy-O—H...O(meth­oxy) and amine-N—H...N(imine). In the crystal, pairwise amine-N—H...S hydrogen bonds give rise to centrosymmetric {...HNCS}₂ synthons, which lead to dimeric aggregates.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.043
• wR factor = 0.121
• Data-to-parameter ratio = 21.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........       H1O2
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........       H1N3
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........       H1N2
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........       H1N3

Alert level G
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         20 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           7 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   4 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
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick 2008); software used to prepare material for publication: SHELXTL (Sheldrick 2008).

1-[(E)-(3-Hydroxy-4-methoxybenzylidene)amino]-3-methylthiourea

Crystal data

C10H13N3O2S	F(000) = 504
Mr = 239.29	Dx = 1.366 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.4893 (13) Å	Cell parameters from 5445 reflections
b = 13.5903 (19) Å	θ = 2.6–27.0°
c = 9.0554 (12) Å	µ = 0.27 mm^−1
β = 94.896 (2)°	T = 100 K
V = 1163.5 (3) Å^3	Block, colourless
Z = 4	0.41 × 0.27 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer	Rint = 0.045
φ and ω scans	θmax = 30.2°, θmin = 2.2°
25305 measured reflections	h = −13→13
3429 independent reflections	k = −19→19
2573 reflections with I > 2σ(I)	l = −12→12

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.121	w = 1/[σ^2(Fo^2) + (0.0492P)^2 + 0.4456P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3429 reflections	Δρmax = 0.33 e Å^−3
159 parameters	Δρmin = −0.25 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
S1	−0.17921 (5)	0.60009 (3)	−0.56327 (4)	0.04224 (14)
O1	0.39288 (13)	0.61470 (9)	0.46152 (13)	0.0438 (3)
O2	0.51572 (14)	0.51474 (12)	0.25548 (15)	0.0540 (4)
N1	0.01610 (15)	0.61303 (10)	−0.16455 (14)	0.0362 (3)
N2	−0.02765 (16)	0.58746 (11)	−0.30889 (16)	0.0392 (3)
N3	−0.19422 (16)	0.70885 (11)	−0.32064 (17)	0.0419 (3)
C1	0.11997 (17)	0.63490 (12)	0.14732 (18)	0.0375 (3)
H1A	0.0295	0.6629	0.1217	0.045*
C2	0.18498 (18)	0.64841 (12)	0.28869 (18)	0.0380 (4)
H2A	0.1391	0.6854	0.3596	0.046*
C3	0.31735 (17)	0.60775 (11)	0.32641 (16)	0.0334 (3)
C4	0.38462 (17)	0.55389 (12)	0.22168 (17)	0.0352 (3)
C5	0.31840 (17)	0.53995 (12)	0.08188 (17)	0.0359 (3)
H5A	0.3636	0.5021	0.0114	0.043*
C6	0.18565 (16)	0.58084 (11)	0.04272 (17)	0.0328 (3)
C7	0.12370 (18)	0.56569 (12)	−0.10845 (18)	0.0369 (3)
H7A	0.1655	0.5182	−0.1681	0.044*
C8	−0.13334 (16)	0.63533 (11)	−0.38644 (17)	0.0334 (3)
C9	−0.3040 (2)	0.77017 (18)	−0.3935 (3)	0.0679 (7)
H9A	−0.3534	0.8053	−0.3187	0.102*
H9B	−0.3715	0.7289	−0.4534	0.102*
H9C	−0.2615	0.8179	−0.4576	0.102*
C10	0.3315 (2)	0.66986 (15)	0.57408 (19)	0.0497 (5)
H10A	0.3935	0.6667	0.6662	0.075*
H10B	0.2389	0.6421	0.5907	0.075*
H10C	0.3201	0.7386	0.5425	0.075*
H1N2	0.013 (2)	0.5400 (15)	−0.352 (2)	0.046 (5)*
H1N3	−0.162 (2)	0.7251 (16)	−0.234 (2)	0.051 (6)*
H1O2	0.542 (3)	0.5280 (18)	0.345 (3)	0.069 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0469 (3)	0.0460 (2)	0.0318 (2)	0.00772 (18)	−0.00814 (17)	−0.00491 (16)
O1	0.0449 (7)	0.0545 (7)	0.0308 (6)	0.0104 (6)	−0.0032 (5)	−0.0084 (5)
O2	0.0429 (7)	0.0768 (10)	0.0400 (7)	0.0263 (7)	−0.0101 (6)	−0.0146 (6)
N1	0.0384 (7)	0.0378 (7)	0.0310 (6)	−0.0014 (5)	−0.0052 (5)	−0.0004 (5)
N2	0.0431 (8)	0.0402 (7)	0.0325 (7)	0.0075 (6)	−0.0081 (6)	−0.0037 (6)
N3	0.0404 (8)	0.0465 (8)	0.0370 (7)	0.0071 (6)	−0.0071 (6)	−0.0097 (6)
C1	0.0308 (8)	0.0407 (8)	0.0408 (8)	0.0046 (6)	0.0014 (6)	0.0026 (7)
C2	0.0373 (8)	0.0417 (8)	0.0357 (8)	0.0057 (7)	0.0064 (6)	−0.0027 (6)
C3	0.0350 (8)	0.0360 (8)	0.0289 (7)	0.0010 (6)	0.0004 (6)	−0.0009 (6)
C4	0.0314 (8)	0.0395 (8)	0.0340 (8)	0.0063 (6)	−0.0008 (6)	−0.0013 (6)
C5	0.0373 (8)	0.0381 (8)	0.0319 (7)	0.0047 (6)	0.0005 (6)	−0.0040 (6)
C6	0.0328 (8)	0.0324 (7)	0.0324 (7)	−0.0019 (6)	−0.0021 (6)	0.0023 (6)
C7	0.0388 (8)	0.0358 (8)	0.0349 (8)	0.0014 (6)	−0.0032 (6)	−0.0012 (6)
C8	0.0323 (8)	0.0337 (7)	0.0333 (7)	−0.0029 (6)	−0.0024 (6)	0.0011 (6)
C9	0.0590 (13)	0.0712 (14)	0.0689 (14)	0.0316 (11)	−0.0215 (11)	−0.0248 (11)
C10	0.0649 (12)	0.0499 (10)	0.0345 (8)	0.0086 (9)	0.0041 (8)	−0.0075 (7)

Geometric parameters (Å, º)

S1—C8	1.6923 (16)	C2—C3	1.388 (2)
O1—C3	1.3675 (18)	C2—H2A	0.9500
O1—C10	1.429 (2)	C3—C4	1.395 (2)
O2—C4	1.3636 (19)	C4—C5	1.377 (2)
O2—H1O2	0.85 (2)	C5—C6	1.395 (2)
N1—C7	1.275 (2)	C5—H5A	0.9500
N1—N2	1.3816 (18)	C6—C7	1.458 (2)
N2—C8	1.342 (2)	C7—H7A	0.9500
N2—H1N2	0.86 (2)	C9—H9A	0.9800
N3—C8	1.321 (2)	C9—H9B	0.9800
N3—C9	1.448 (2)	C9—H9C	0.9800
N3—H1N3	0.85 (2)	C10—H10A	0.9800
C1—C2	1.385 (2)	C10—H10B	0.9800
C1—C6	1.388 (2)	C10—H10C	0.9800
C1—H1A	0.9500
C3—O1—C10	117.40 (13)	C6—C5—H5A	119.7
C4—O2—H1O2	108.9 (17)	C1—C6—C5	119.07 (14)
C7—N1—N2	114.56 (14)	C1—C6—C7	123.17 (14)
C8—N2—N1	121.58 (14)	C5—C6—C7	117.75 (14)
C8—N2—H1N2	118.1 (13)	N1—C7—C6	123.22 (15)
N1—N2—H1N2	120.3 (13)	N1—C7—H7A	118.4
C8—N3—C9	123.71 (15)	C6—C7—H7A	118.4
C8—N3—H1N3	118.7 (14)	N3—C8—N2	117.80 (14)
C9—N3—H1N3	117.3 (14)	N3—C8—S1	123.62 (12)
C2—C1—C6	120.69 (15)	N2—C8—S1	118.57 (13)
C2—C1—H1A	119.7	N3—C9—H9A	109.5
C6—C1—H1A	119.7	N3—C9—H9B	109.5
C1—C2—C3	119.80 (15)	H9A—C9—H9B	109.5
C1—C2—H2A	120.1	N3—C9—H9C	109.5
C3—C2—H2A	120.1	H9A—C9—H9C	109.5
O1—C3—C2	125.93 (14)	H9B—C9—H9C	109.5
O1—C3—C4	114.16 (14)	O1—C10—H10A	109.5
C2—C3—C4	119.91 (14)	O1—C10—H10B	109.5
O2—C4—C5	119.24 (14)	H10A—C10—H10B	109.5
O2—C4—C3	120.91 (14)	O1—C10—H10C	109.5
C5—C4—C3	119.85 (14)	H10A—C10—H10C	109.5
C4—C5—C6	120.67 (14)	H10B—C10—H10C	109.5
C4—C5—H5A	119.7
C7—N1—N2—C8	−175.40 (16)	C2—C1—C6—C5	0.1 (2)
C6—C1—C2—C3	0.1 (3)	C2—C1—C6—C7	−178.82 (15)
C10—O1—C3—C2	−0.9 (2)	C4—C5—C6—C1	−0.8 (2)
C10—O1—C3—C4	179.23 (15)	C4—C5—C6—C7	178.14 (15)
C1—C2—C3—O1	−179.53 (15)	N2—N1—C7—C6	−179.36 (15)
C1—C2—C3—C4	0.3 (3)	C1—C6—C7—N1	11.6 (3)
O1—C3—C4—O2	−1.3 (2)	C5—C6—C7—N1	−167.35 (16)
C2—C3—C4—O2	178.84 (16)	C9—N3—C8—N2	176.56 (19)
O1—C3—C4—C5	178.83 (15)	C9—N3—C8—S1	−2.2 (3)
C2—C3—C4—C5	−1.0 (2)	N1—N2—C8—N3	0.5 (2)
O2—C4—C5—C6	−178.58 (15)	N1—N2—C8—S1	179.36 (12)
C3—C4—C5—C6	1.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1	0.85 (3)	2.18 (3)	2.6564 (19)	115 (2)
N3—H1N3···N1	0.847 (19)	2.32 (2)	2.682 (2)	106.1 (16)
N2—H1N2···S1^i	0.86 (2)	2.63 (2)	3.4753 (16)	167.8 (16)
N3—H1N3···S1^ii	0.847 (19)	2.85 (2)	3.4839 (16)	133.5 (17)

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