[1-(2-Hydroxy­ethyl)imidazolidin-2-yl­idene]malononitrile

Inter­molecular hydrogen bonds connect the mol­ecules of the title compound, C₈H₁₀N₄O, into centrosymmetric dimers. These dimers are further linked into chains by another inter­molecular hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.128
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C6     -   C7      ..       6.05 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C6     -   C8      ..       5.65 su
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         18
            C8  -C6  -C7  -N3     -7.00  8.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         19
            C1  -C6  -C7  -N3    171.00  7.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         20
            C7  -C6  -C8  -N4    111.00 17.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         21
            C1  -C6  -C8  -N4    -67.00 17.00   1.555   1.555   1.555   1.555

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

[1-(2-Hydroxyethyl)imidazolidin-2-ylidene]malononitrile

Crystal data

C8H10N4O	F(000) = 376
Mr = 178.20	Dx = 1.346 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.549 (2) Å	Cell parameters from 1018 reflections
b = 8.462 (3) Å	θ = 2.7–22.4°
c = 13.788 (4) Å	µ = 0.10 mm^−1
β = 93.301 (6)°	T = 293 K
V = 879.4 (5) Å^3	Block, colourless
Z = 4	0.30 × 0.26 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1795 independent reflections
Radiation source: fine-focus sealed tube	992 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
φ and ω scans	θmax = 26.4°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −8→9
Tmin = 0.972, Tmax = 0.979	k = −10→10
4826 measured reflections	l = −14→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.128	w = 1/[σ^2(Fo^2) + (0.0598P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.002
1795 reflections	Δρmax = 0.20 e Å^−3
120 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.029 (5)

Special details

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.

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

	x	y	z	Uiso*/Ueq
O1	0.9007 (2)	0.1271 (2)	0.81008 (11)	0.0586 (6)
H1	0.9801	0.1434	0.7732	0.088*
N1	0.8072 (2)	0.23511 (19)	0.49038 (12)	0.0446 (5)
H1A	0.8561	0.2238	0.4360	0.054*
N2	0.6880 (2)	0.16981 (19)	0.62591 (11)	0.0385 (5)
N3	0.6190 (3)	−0.2803 (3)	0.59464 (17)	0.0743 (7)
N4	0.8526 (3)	−0.0954 (2)	0.33894 (14)	0.0605 (6)
C1	0.7449 (3)	0.1160 (2)	0.54180 (14)	0.0344 (5)
C2	0.7825 (4)	0.3854 (3)	0.53736 (16)	0.0607 (8)
H2A	0.6980	0.4506	0.4999	0.073*
H2B	0.8940	0.4421	0.5464	0.073*
C3	0.7126 (4)	0.3402 (3)	0.63287 (16)	0.0598 (8)
H3A	0.7969	0.3670	0.6861	0.072*
H3B	0.6010	0.3931	0.6426	0.072*
C4	0.6313 (3)	0.0802 (3)	0.70841 (14)	0.0440 (6)
H4A	0.5534	−0.0044	0.6850	0.053*
H4B	0.5637	0.1489	0.7488	0.053*
C5	0.7836 (3)	0.0101 (3)	0.76952 (16)	0.0533 (7)
H5A	0.7369	−0.0515	0.8216	0.064*
H5B	0.8495	−0.0609	0.7297	0.064*
C6	0.7408 (3)	−0.0414 (2)	0.50744 (14)	0.0367 (5)
C7	0.6735 (3)	−0.1713 (3)	0.55680 (16)	0.0459 (6)
C8	0.8033 (3)	−0.0717 (2)	0.41508 (16)	0.0419 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0630 (13)	0.0767 (13)	0.0367 (9)	−0.0052 (9)	0.0099 (8)	−0.0122 (8)
N1	0.0625 (14)	0.0373 (11)	0.0357 (10)	0.0025 (9)	0.0174 (9)	0.0027 (8)
N2	0.0521 (13)	0.0341 (10)	0.0303 (10)	0.0027 (9)	0.0104 (8)	−0.0006 (8)
N3	0.110 (2)	0.0456 (13)	0.0689 (15)	−0.0090 (13)	0.0217 (14)	0.0032 (11)
N4	0.0665 (16)	0.0722 (15)	0.0441 (12)	−0.0006 (11)	0.0140 (10)	−0.0145 (10)
C1	0.0357 (14)	0.0388 (13)	0.0288 (11)	0.0034 (9)	0.0019 (9)	0.0028 (9)
C2	0.093 (2)	0.0416 (14)	0.0494 (16)	−0.0083 (14)	0.0171 (14)	−0.0029 (11)
C3	0.094 (2)	0.0388 (15)	0.0489 (15)	0.0059 (13)	0.0208 (14)	−0.0047 (11)
C4	0.0511 (16)	0.0489 (14)	0.0335 (12)	−0.0008 (12)	0.0157 (11)	0.0000 (10)
C5	0.073 (2)	0.0509 (15)	0.0374 (13)	−0.0038 (14)	0.0104 (12)	0.0055 (11)
C6	0.0441 (14)	0.0347 (12)	0.0321 (11)	0.0013 (10)	0.0085 (9)	−0.0021 (9)
C7	0.0581 (17)	0.0387 (14)	0.0415 (13)	0.0043 (12)	0.0078 (11)	−0.0051 (11)
C8	0.0431 (15)	0.0423 (14)	0.0402 (13)	0.0018 (11)	0.0022 (11)	−0.0044 (10)

Geometric parameters (Å, º)

O1—C5	1.420 (3)	C2—H2A	0.9700
O1—H1	0.8200	C2—H2B	0.9700
N1—C1	1.334 (2)	C3—H3A	0.9700
N1—C2	1.444 (3)	C3—H3B	0.9700
N1—H1A	0.8600	C4—C5	1.508 (3)
N2—C1	1.340 (2)	C4—H4A	0.9700
N2—C4	1.452 (2)	C4—H4B	0.9700
N2—C3	1.456 (3)	C5—H5A	0.9700
N3—C7	1.147 (3)	C5—H5B	0.9700
N4—C8	1.151 (3)	C6—C7	1.404 (3)
C1—C6	1.414 (3)	C6—C8	1.407 (3)
C2—C3	1.496 (3)
C5—O1—H1	109.5	C2—C3—H3B	110.9
C1—N1—C2	111.63 (17)	H3A—C3—H3B	108.9
C1—N1—H1A	124.2	N2—C4—C5	113.16 (19)
C2—N1—H1A	124.2	N2—C4—H4A	108.9
C1—N2—C4	128.64 (17)	C5—C4—H4A	108.9
C1—N2—C3	110.34 (16)	N2—C4—H4B	108.9
C4—N2—C3	120.52 (16)	C5—C4—H4B	108.9
N1—C1—N2	110.11 (18)	H4A—C4—H4B	107.8
N1—C1—C6	122.39 (18)	O1—C5—C4	112.52 (19)
N2—C1—C6	127.49 (18)	O1—C5—H5A	109.1
N1—C2—C3	103.34 (18)	C4—C5—H5A	109.1
N1—C2—H2A	111.1	O1—C5—H5B	109.1
C3—C2—H2A	111.1	C4—C5—H5B	109.1
N1—C2—H2B	111.1	H5A—C5—H5B	107.8
C3—C2—H2B	111.1	C7—C6—C8	116.48 (18)
H2A—C2—H2B	109.1	C7—C6—C1	125.25 (18)
N2—C3—C2	104.19 (17)	C8—C6—C1	118.23 (18)
N2—C3—H3A	110.9	N3—C7—C6	177.9 (2)
C2—C3—H3A	110.9	N4—C8—C6	179.1 (3)
N2—C3—H3B	110.9
C2—N1—C1—N2	−4.2 (3)	C3—N2—C4—C5	−94.5 (2)
C2—N1—C1—C6	174.9 (2)	N2—C4—C5—O1	61.0 (2)
C4—N2—C1—N1	−171.5 (2)	N1—C1—C6—C7	−178.5 (2)
C3—N2—C1—N1	0.2 (3)	N2—C1—C6—C7	0.4 (4)
C4—N2—C1—C6	9.4 (4)	N1—C1—C6—C8	−0.7 (3)
C3—N2—C1—C6	−178.8 (2)	N2—C1—C6—C8	178.2 (2)
C1—N1—C2—C3	6.2 (3)	C8—C6—C7—N3	−7 (8)
C1—N2—C3—C2	3.6 (3)	C1—C6—C7—N3	171 (7)
C4—N2—C3—C2	176.1 (2)	C7—C6—C8—N4	111 (17)
N1—C2—C3—N2	−5.6 (3)	C1—C6—C8—N4	−67 (17)
C1—N2—C4—C5	76.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N4^i	0.82	2.09	2.864 (3)	157
N1—H1A···O1^ii	0.86	2.19	2.870 (2)	136

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