[(E)-(1-Phenyl-ethyl-idene)amino]-urea methanol monosolvate.

In the title compound, C(9)H(11)N(3)O·CH(4)O, the semicarbazone moiety is nearly planar [maximum deviation = 0.017 (2) Å] and is twisted by a dihedral angle of 29.40 (13)° with respect to the phenyl ring. The semicarbazone moiety and phenyl ring are located on opposite sides of the C=N bond, showing the E configuration. An inter-molecular O-H⋯O and N-H⋯O hydrogen-bonding network occurs in the crystal structure.

Related literature

For general background and applications of semicarbazone derivatives, see: Chandra & Gupta (2005 ▶). For related structures, see: Fun et al. (2009a ▶,b ▶).

Experimental

Crystal data

C9H11N3O·CH4O

M = 209.25

Monoclinic,

a = 6.629 (3) Å

b = 8.371 (4) Å

c = 20.329 (9) Å

β = 99.181 (5)°

V = 1113.6 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.24 × 0.22 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

8148 measured reflections

2057 independent reflections

1617 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.128

S = 1.07

2057 reflections

140 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000225/xu5132sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000225/xu5132Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H11N3O·CH4O	F(000) = 448
Mr = 209.25	Dx = 1.248 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2808 reflections
a = 6.629 (3) Å	θ = 2.6–28.2°
b = 8.371 (4) Å	µ = 0.09 mm−1
c = 20.329 (9) Å	T = 296 K
β = 99.181 (5)°	Block, colourless
V = 1113.6 (8) Å3	0.24 × 0.22 × 0.18 mm
Z = 4

Bruker APEXII CCD diffractometer	1617 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
graphite	θmax = 25.5°, θmin = 2.6°
φ and ω scans	h = −8→8
8148 measured reflections	k = −9→10
2057 independent reflections	l = −24→24

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.0583P)2 + 0.3389P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
2057 reflections	Δρmax = 0.26 e Å−3
140 parameters	Δρmin = −0.18 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.020 (4)

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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.0487 (3)	0.6825 (3)	0.73837 (11)	0.0636 (6)
H1	0.0233	0.7479	0.7010	0.076*
C2	−0.0980 (3)	0.5772 (3)	0.75182 (11)	0.0630 (6)
H2	−0.2233	0.5717	0.7238	0.076*
C3	−0.0590 (3)	0.4793 (3)	0.80720 (10)	0.0550 (6)
H3	−0.1582	0.4076	0.8163	0.066*
C4	0.1262 (3)	0.4875 (2)	0.84901 (9)	0.0438 (5)
H4	0.1504	0.4216	0.8863	0.053*
C5	0.2773 (2)	0.5931 (2)	0.83614 (8)	0.0371 (4)
C6	0.2342 (3)	0.6916 (2)	0.78033 (10)	0.0521 (5)
H6	0.3319	0.7645	0.7712	0.063*
C7	0.6059 (3)	0.7470 (2)	0.88452 (10)	0.0509 (5)
H7A	0.6457	0.7752	0.9305	0.076*
H7B	0.5268	0.8322	0.8617	0.076*
H7C	0.7257	0.7294	0.8645	0.076*
C8	0.4800 (2)	0.5973 (2)	0.87964 (8)	0.0362 (4)
C9	0.7858 (2)	0.3143 (2)	0.97715 (8)	0.0361 (4)
C10	0.0959 (4)	0.0359 (3)	0.89062 (11)	0.0673 (6)
H10A	−0.0277	0.0967	0.8798	0.101*
H10B	0.0627	−0.0746	0.8957	0.101*
H10C	0.1762	0.0466	0.8555	0.101*
N1	0.5332 (2)	0.46585 (17)	0.91022 (7)	0.0362 (4)
N2	0.7209 (2)	0.45770 (17)	0.95027 (7)	0.0398 (4)
H8	0.7957	0.5416	0.9582	0.048*
O1	0.96431 (17)	0.30074 (14)	1.00688 (6)	0.0458 (4)
N3	0.6552 (2)	0.19317 (18)	0.96944 (9)	0.0526 (5)
H3A	0.6927	0.1007	0.9853	0.063*
H3B	0.5330	0.2071	0.9486	0.063*
O2	0.20857 (19)	0.09309 (17)	0.95077 (7)	0.0544 (4)
H2A	0.1370	0.1538	0.9688	0.082*

	U11	U22	U33	U12	U13	U23
C1	0.0641 (14)	0.0727 (15)	0.0482 (12)	0.0140 (12)	−0.0092 (10)	0.0110 (11)
C2	0.0449 (11)	0.0791 (16)	0.0569 (13)	0.0150 (11)	−0.0162 (10)	−0.0122 (12)
C3	0.0361 (10)	0.0651 (13)	0.0613 (13)	−0.0020 (9)	0.0001 (9)	−0.0118 (11)
C4	0.0392 (9)	0.0484 (11)	0.0427 (10)	0.0015 (8)	0.0032 (8)	0.0004 (8)
C5	0.0372 (9)	0.0385 (9)	0.0344 (9)	0.0060 (7)	0.0021 (7)	−0.0030 (7)
C6	0.0502 (11)	0.0547 (12)	0.0484 (11)	0.0029 (9)	−0.0009 (9)	0.0092 (9)
C7	0.0467 (10)	0.0442 (11)	0.0569 (12)	−0.0038 (8)	−0.0063 (9)	0.0047 (9)
C8	0.0360 (9)	0.0400 (10)	0.0319 (9)	0.0005 (7)	0.0030 (7)	0.0003 (7)
C9	0.0318 (8)	0.0383 (9)	0.0365 (9)	−0.0005 (7)	0.0008 (7)	0.0000 (7)
C10	0.0706 (14)	0.0675 (15)	0.0605 (14)	−0.0034 (12)	0.0005 (12)	−0.0025 (11)
N1	0.0310 (7)	0.0409 (8)	0.0346 (8)	−0.0004 (6)	−0.0012 (6)	0.0024 (6)
N2	0.0334 (7)	0.0370 (8)	0.0450 (9)	−0.0043 (6)	−0.0058 (6)	0.0042 (6)
O1	0.0337 (7)	0.0422 (7)	0.0562 (8)	0.0000 (5)	−0.0085 (6)	0.0011 (6)
N3	0.0356 (8)	0.0401 (9)	0.0758 (12)	−0.0042 (7)	−0.0096 (8)	0.0125 (8)
O2	0.0420 (7)	0.0510 (9)	0.0658 (9)	0.0044 (6)	−0.0047 (6)	−0.0037 (7)

C1—C2	1.372 (3)	C7—H7C	0.9600
C1—C6	1.382 (3)	C8—N1	1.285 (2)
C1—H1	0.9300	C9—O1	1.2453 (19)
C2—C3	1.383 (3)	C9—N3	1.326 (2)
C2—H2	0.9300	C9—N2	1.360 (2)
C3—C4	1.379 (2)	C10—O2	1.411 (2)
C3—H3	0.9300	C10—H10A	0.9600
C4—C5	1.391 (3)	C10—H10B	0.9600
C4—H4	0.9300	C10—H10C	0.9600
C5—C6	1.395 (3)	N1—N2	1.3757 (18)
C5—C8	1.486 (2)	N2—H8	0.8600
C6—H6	0.9300	N3—H3A	0.8600
C7—C8	1.500 (3)	N3—H3B	0.8600
C7—H7A	0.9600	O2—H2A	0.8200
C7—H7B	0.9600
C2—C1—C6	120.1 (2)	H7A—C7—H7C	109.5
C2—C1—H1	120.0	H7B—C7—H7C	109.5
C6—C1—H1	120.0	N1—C8—C5	114.83 (15)
C1—C2—C3	119.75 (18)	N1—C8—C7	125.18 (15)
C1—C2—H2	120.1	C5—C8—C7	119.98 (15)
C3—C2—H2	120.1	O1—C9—N3	122.64 (15)
C4—C3—C2	120.3 (2)	O1—C9—N2	119.38 (15)
C4—C3—H3	119.8	N3—C9—N2	117.96 (14)
C2—C3—H3	119.8	O2—C10—H10A	109.5
C3—C4—C5	120.83 (18)	O2—C10—H10B	109.5
C3—C4—H4	119.6	H10A—C10—H10B	109.5
C5—C4—H4	119.6	O2—C10—H10C	109.5
C4—C5—C6	117.92 (16)	H10A—C10—H10C	109.5
C4—C5—C8	120.83 (15)	H10B—C10—H10C	109.5
C6—C5—C8	121.22 (16)	C8—N1—N2	118.77 (14)
C1—C6—C5	121.1 (2)	C9—N2—N1	118.67 (13)
C1—C6—H6	119.5	C9—N2—H8	120.7
C5—C6—H6	119.5	N1—N2—H8	120.7
C8—C7—H7A	109.5	C9—N3—H3A	120.0
C8—C7—H7B	109.5	C9—N3—H3B	120.0
H7A—C7—H7B	109.5	H3A—N3—H3B	120.0
C8—C7—H7C	109.5	C10—O2—H2A	109.5
C6—C1—C2—C3	−0.5 (3)	C6—C5—C8—N1	−152.23 (17)
C1—C2—C3—C4	0.2 (3)	C4—C5—C8—C7	−154.55 (18)
C2—C3—C4—C5	−0.4 (3)	C6—C5—C8—C7	27.1 (3)
C3—C4—C5—C6	0.9 (3)	C5—C8—N1—N2	178.39 (14)
C3—C4—C5—C8	−177.47 (17)	C7—C8—N1—N2	−0.9 (3)
C2—C1—C6—C5	1.0 (3)	O1—C9—N2—N1	171.57 (15)
C4—C5—C6—C1	−1.2 (3)	N3—C9—N2—N1	−7.4 (2)
C8—C5—C6—C1	177.18 (18)	C8—N1—N2—C9	−173.38 (16)
C4—C5—C8—N1	26.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1i	0.82	1.93	2.745 (2)	177
N2—H8···O1ii	0.86	2.10	2.936 (2)	164
N3—H3A···O2iii	0.86	2.12	2.953 (2)	164
N3—H3B···O2	0.86	2.36	3.042 (2)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1i	0.82	1.93	2.745 (2)	177
N2—H8⋯O1ii	0.86	2.10	2.936 (2)	164
N3—H3A⋯O2iii	0.86	2.12	2.953 (2)	164
N3—H3B⋯O2	0.86	2.36	3.042 (2)	137

Symmetry codes: (i) ; (ii) ; (iii) .