Creatininium cinnamate.

THE CRYSTAL STRUCTURE OF THE TITLE COMPOUND (SYSTEMATIC NAME: 2-amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-3-ium 3-phenyl-prop-2-enoate), C(4)H(8)N(3)O(+)·C(9)H(7)O(2) (-), is stabilized by N-H⋯O hydrogen bonding. Cations are linked to anions to form ion pairs with an R(2) (2)(8) ring motif. These ion pairs are connected through a C(2) (2)(6) chain motif extending along the c axis of the unit cell. This crystal packing is characterized by hydro-phobic layers at x ∼ 1/2 packed between hydro-philic layers at x ∼ 0.

Related literature

For related structures, see: Bahadur, Kannan et al. (2007 ▶); Bahadur, Sivapragasam et al. (2007 ▶); Bahadur, Rajalakshmi et al. (2007 ▶). For hydrogen-bonding motif notation, see: Bernstein et al. (1995 ▶). For crystal engineering, see: Desiraju (1989 ▶). For information about n class="Chemical">creatinine and its biological significance, see: Madaras & Buck (1996 ▶); Sharma et al. (2004 ▶); Narayanan & Appleton (1980 ▶).

Experimental

Crystal data

C4H8N3O+·C9H7O2 −

M = 261.28

Monoclinic,

a = 9.1680 (8) Å

b = 11.3391 (11) Å

c = 12.7070 (12) Å

β = 104.578 (2)°

V = 1278.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.25 × 0.22 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

9014 measured reflections

2250 independent reflections

2037 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.100

S = 1.05

2250 reflections

186 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL/PC; molecular graphics: Mercury (Macrae et al., 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811016916/bt5542sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016916/bt5542Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811016916/bt5542Isup3.cml

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

C4H8N3O+·C9H7O2−	F(000) = 552
Mr = 261.28	Dx = 1.357 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3849 reflections
a = 9.1680 (8) Å	θ = 2.1–24.5°
b = 11.3391 (11) Å	µ = 0.10 mm−1
c = 12.7070 (12) Å	T = 293 K
β = 104.578 (2)°	Block, colourless
V = 1278.5 (2) Å3	0.25 × 0.22 × 0.18 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2037 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
graphite	θmax = 25.0°, θmin = 2.3°
ω scans	h = −10→10
9014 measured reflections	k = −13→13
2250 independent reflections	l = −15→15

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)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0546P)2 + 0.2262P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2250 reflections	Δρmax = 0.16 e Å−3
186 parameters	Δρmin = −0.14 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.047 (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
C11	0.90518 (15)	−0.14215 (12)	0.42786 (10)	0.0444 (3)
C12	0.82555 (14)	−0.03500 (11)	0.37734 (10)	0.0425 (3)
H12	0.8449	−0.0046	0.3142	0.051*
C13	0.72755 (15)	0.01743 (12)	0.42137 (10)	0.0465 (3)
H13	0.7159	−0.0168	0.4853	0.056*
C14	0.63452 (14)	0.12096 (11)	0.38527 (10)	0.0431 (3)
C15	0.61909 (16)	0.17391 (12)	0.28495 (11)	0.0501 (3)
H15	0.6716	0.1446	0.2368	0.060*
C16	0.52597 (19)	0.26999 (14)	0.25656 (13)	0.0620 (4)
H16	0.5149	0.3046	0.1887	0.074*
C17	0.44942 (18)	0.31527 (14)	0.32702 (14)	0.0627 (4)
H17	0.3885	0.3813	0.3076	0.075*
C18	0.46263 (19)	0.26350 (16)	0.42554 (14)	0.0685 (5)
H18	0.4099	0.2934	0.4733	0.082*
C19	0.55385 (19)	0.16718 (15)	0.45395 (12)	0.0616 (4)
H19	0.5618	0.1319	0.5212	0.074*
C5	0.88984 (14)	0.38873 (11)	0.37801 (10)	0.0404 (3)
C3	0.78741 (16)	0.45605 (12)	0.50957 (11)	0.0490 (3)
C2	0.74062 (17)	0.53562 (12)	0.41229 (11)	0.0514 (4)
H2A	0.6319	0.5368	0.3846	0.062*
H2B	0.7763	0.6155	0.4299	0.062*
C1	0.8109 (2)	0.53413 (16)	0.23096 (13)	0.0705 (5)
H1A	0.8739	0.6030	0.2417	0.106*
H1B	0.7096	0.5559	0.1944	0.106*
H1C	0.8481	0.4779	0.1875	0.106*
N1	0.81251 (13)	0.48238 (10)	0.33492 (9)	0.0477 (3)
N4	0.87699 (13)	0.37178 (10)	0.48180 (9)	0.0445 (3)
N5	0.96941 (14)	0.32061 (11)	0.33272 (10)	0.0490 (3)
O11	0.99961 (12)	−0.18945 (8)	0.38395 (8)	0.0530 (3)
O12	0.87297 (14)	−0.18107 (10)	0.51056 (9)	0.0711 (4)
O1	0.75459 (15)	0.46421 (10)	0.59527 (9)	0.0710 (4)
H4	0.9161 (18)	0.3101 (15)	0.5239 (14)	0.060 (5)*
H5A	0.9778 (18)	0.3305 (14)	0.2643 (15)	0.058 (4)*
H5B	1.0243 (19)	0.2638 (16)	0.3789 (15)	0.066 (5)*

	U11	U22	U33	U12	U13	U23
C11	0.0542 (7)	0.0438 (7)	0.0369 (6)	0.0026 (6)	0.0146 (5)	0.0020 (5)
C12	0.0507 (7)	0.0421 (7)	0.0361 (6)	0.0009 (5)	0.0134 (5)	0.0027 (5)
C13	0.0584 (8)	0.0485 (7)	0.0338 (6)	0.0048 (6)	0.0137 (6)	0.0018 (5)
C14	0.0480 (7)	0.0435 (7)	0.0385 (7)	0.0017 (5)	0.0125 (5)	−0.0033 (5)
C15	0.0614 (8)	0.0500 (8)	0.0425 (7)	0.0052 (6)	0.0196 (6)	−0.0004 (6)
C16	0.0775 (10)	0.0569 (9)	0.0514 (8)	0.0108 (8)	0.0155 (7)	0.0125 (7)
C17	0.0643 (9)	0.0541 (9)	0.0671 (10)	0.0176 (7)	0.0116 (8)	0.0003 (7)
C18	0.0749 (10)	0.0713 (11)	0.0660 (10)	0.0226 (9)	0.0301 (8)	−0.0061 (8)
C19	0.0767 (10)	0.0682 (10)	0.0463 (8)	0.0190 (8)	0.0276 (7)	0.0051 (7)
C5	0.0469 (7)	0.0404 (7)	0.0353 (6)	−0.0022 (5)	0.0130 (5)	0.0000 (5)
C3	0.0625 (8)	0.0446 (7)	0.0451 (7)	0.0008 (6)	0.0231 (6)	−0.0030 (6)
C2	0.0596 (8)	0.0469 (8)	0.0507 (8)	0.0092 (6)	0.0196 (6)	0.0002 (6)
C1	0.0960 (12)	0.0713 (11)	0.0481 (9)	0.0244 (9)	0.0257 (8)	0.0208 (7)
N1	0.0600 (7)	0.0469 (6)	0.0385 (6)	0.0083 (5)	0.0165 (5)	0.0061 (5)
N4	0.0596 (7)	0.0415 (6)	0.0363 (6)	0.0050 (5)	0.0194 (5)	0.0036 (5)
N5	0.0634 (7)	0.0509 (7)	0.0374 (6)	0.0112 (6)	0.0216 (5)	0.0045 (5)
O11	0.0690 (6)	0.0500 (6)	0.0451 (5)	0.0160 (4)	0.0240 (5)	0.0054 (4)
O12	0.0861 (8)	0.0757 (8)	0.0637 (7)	0.0326 (6)	0.0415 (6)	0.0330 (6)
O1	0.1074 (9)	0.0644 (7)	0.0550 (6)	0.0145 (6)	0.0460 (6)	−0.0001 (5)

C11—O12	1.2419 (16)	C19—H19	0.9300
C11—O11	1.2616 (16)	C5—N5	1.2928 (17)
C11—C12	1.4784 (18)	C5—N1	1.3170 (16)
C12—C13	1.3140 (18)	C5—N4	1.3669 (16)
C12—H12	0.9300	C3—O1	1.2041 (16)
C13—C14	1.4558 (19)	C3—N4	1.3631 (17)
C13—H13	0.9300	C2—N1	1.4462 (16)
C14—C19	1.3814 (18)	C2—H2A	0.9700
C14—C15	1.3836 (19)	C2—H2B	0.9700
C15—C16	1.375 (2)	C1—N1	1.4422 (17)
C15—H15	0.9300	C1—H1A	0.9600
C16—C17	1.369 (2)	C1—H1B	0.9600
C16—H16	0.9300	C1—H1C	0.9600
C17—C18	1.360 (2)	N4—H4	0.899 (18)
C17—H17	0.9300	N5—H5A	0.899 (18)
C18—C19	1.368 (2)	N5—H5B	0.929 (19)
C18—H18	0.9300
O12—C11—O11	123.98 (12)	N5—C5—N1	126.99 (12)
O12—C11—C12	117.57 (11)	N5—C5—N4	122.74 (12)
O11—C11—C12	118.44 (11)	N1—C5—N4	110.27 (11)
C13—C12—C11	120.18 (12)	O1—C3—N4	126.30 (13)
C13—C12—H12	119.9	O1—C3—C2	127.81 (13)
C11—C12—H12	119.9	N4—C3—C2	105.88 (11)
C12—C13—C14	129.78 (12)	N1—C2—C3	102.94 (11)
C12—C13—H13	115.1	N1—C2—H2A	111.2
C14—C13—H13	115.1	C3—C2—H2A	111.2
C19—C14—C15	118.07 (13)	N1—C2—H2B	111.2
C19—C14—C13	118.11 (12)	C3—C2—H2B	111.2
C15—C14—C13	123.79 (11)	H2A—C2—H2B	109.1
C16—C15—C14	119.89 (13)	N1—C1—H1A	109.5
C16—C15—H15	120.1	N1—C1—H1B	109.5
C14—C15—H15	120.1	H1A—C1—H1B	109.5
C17—C16—C15	120.80 (14)	N1—C1—H1C	109.5
C17—C16—H16	119.6	H1A—C1—H1C	109.5
C15—C16—H16	119.6	H1B—C1—H1C	109.5
C18—C17—C16	119.90 (14)	C5—N1—C1	126.10 (12)
C18—C17—H17	120.0	C5—N1—C2	110.10 (10)
C16—C17—H17	120.0	C1—N1—C2	123.47 (12)
C17—C18—C19	119.63 (14)	C3—N4—C5	110.80 (11)
C17—C18—H18	120.2	C3—N4—H4	124.6 (10)
C19—C18—H18	120.2	C5—N4—H4	124.4 (10)
C18—C19—C14	121.69 (14)	C5—N5—H5A	123.4 (10)
C18—C19—H19	119.2	C5—N5—H5B	114.2 (10)
C14—C19—H19	119.2	H5A—N5—H5B	122.2 (14)
O12—C11—C12—C13	1.7 (2)	O1—C3—C2—N1	−179.68 (15)
O11—C11—C12—C13	−179.30 (13)	N4—C3—C2—N1	0.82 (15)
C11—C12—C13—C14	−178.52 (13)	N5—C5—N1—C1	−5.5 (2)
C12—C13—C14—C19	−172.03 (15)	N4—C5—N1—C1	173.73 (14)
C12—C13—C14—C15	9.8 (2)	N5—C5—N1—C2	−179.12 (13)
C19—C14—C15—C16	0.3 (2)	N4—C5—N1—C2	0.16 (15)
C13—C14—C15—C16	178.51 (14)	C3—C2—N1—C5	−0.60 (15)
C14—C15—C16—C17	0.9 (2)	C3—C2—N1—C1	−174.38 (14)
C15—C16—C17—C18	−1.4 (3)	O1—C3—N4—C5	179.71 (15)
C16—C17—C18—C19	0.7 (3)	C2—C3—N4—C5	−0.79 (15)
C17—C18—C19—C14	0.5 (3)	N5—C5—N4—C3	179.74 (12)
C15—C14—C19—C18	−1.0 (2)	N1—C5—N4—C3	0.43 (15)
C13—C14—C19—C18	−179.29 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O11i	0.899 (18)	1.840 (18)	2.7373 (15)	177 (2)
N5—H5A···O11ii	0.899 (18)	1.959 (18)	2.8403 (16)	166 (1)
N5—H5B···O12i	0.929 (19)	1.754 (19)	2.6663 (16)	167 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O11i	0.899 (18)	1.840 (18)	2.7373 (15)	177 (2)
N5—H5A⋯O11ii	0.899 (18)	1.959 (18)	2.8403 (16)	166 (1)
N5—H5B⋯O12i	0.929 (19)	1.754 (19)	2.6663 (16)	167 (2)

Symmetry codes: (i) ; (ii) .