tert-Butyl 4-formyl-1H-imidazole-1-carboxyl-ate.

In the crystal structure of the title compound, C(9)H(12)N(2)O(3), weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into chains. Further weak C-H⋯O hydrogen bonds together with π-π inter-actions [centroid-centroid distance = 3.672 (4) Å] between neighbouring chains lead to a double-chain structure propagating in [100].

Related literature

For uses of imidazole direvatives, see: Matuszak et al. (1976 ▶), Verras et al. (2004 ▶). For the synthesis of the title compound, see: Metobo et al. (2006 ▶).

Experimental

Crystal data

C9H12N2O3

M = 196.21

Triclinic,

a = 5.972 (3) Å

b = 7.173 (7) Å

c = 12.164 (11) Å

α = 79.630 (16)°

β = 86.620 (15)°

γ = 89.326 (15)°

V = 511.7 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.14 × 0.11 × 0.03 mm

Data collection

Bruker APEX CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.987, T max = 0.997

2633 measured reflections

1769 independent reflections

915 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.149

S = 0.99

1769 reflections

130 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810029247/su2164sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029247/su2164Isup2.hkl

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

C9H12N2O3	V = 511.7 (8) Å3
Mr = 196.21	Z = 2
Triclinic, P1	F(000) = 208
Hall symbol: -P 1	Dx = 1.274 Mg m−3
a = 5.972 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.173 (7) Å	Cell parameters from 360 reflections
c = 12.164 (11) Å	µ = 0.10 mm−1
α = 79.630 (16)°	T = 293 K
β = 86.620 (15)°	Plate, colourless
γ = 89.326 (15)°	0.14 × 0.11 × 0.03 mm

Bruker APEX CCD area detector diffractometer	1769 independent reflections
Radiation source: fine-focus sealed tube	915 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→7
Tmin = 0.987, Tmax = 0.997	k = −8→8
2633 measured reflections	l = −14→8

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0655P)2] where P = (Fo2 + 2Fc2)/3
1769 reflections	(Δ/σ)max < 0.001
130 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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.

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
O1	0.3982 (5)	0.3453 (4)	0.8094 (2)	0.0910 (9)
O2	0.3540 (3)	0.2118 (3)	0.27957 (17)	0.0501 (6)
O3	−0.0065 (4)	0.2329 (4)	0.34612 (19)	0.0794 (9)
N1	0.5369 (4)	0.2729 (4)	0.5822 (2)	0.0562 (8)
N2	0.2860 (4)	0.2475 (4)	0.4569 (2)	0.0480 (7)
C1	0.3197 (5)	0.2938 (4)	0.6277 (3)	0.0505 (9)
C2	0.5087 (5)	0.2466 (4)	0.4808 (3)	0.0503 (9)
H2	0.6262	0.2289	0.4301	0.060*
C3	0.1660 (5)	0.2779 (4)	0.5522 (3)	0.0529 (9)
H3	0.0110	0.2859	0.5627	0.063*
C4	0.2649 (7)	0.3323 (5)	0.7404 (3)	0.0668 (11)
H4	0.1142	0.3480	0.7606	0.080*
C5	0.1920 (6)	0.2290 (5)	0.3551 (3)	0.0519 (9)
C6	0.3044 (5)	0.1971 (5)	0.1619 (3)	0.0470 (8)
C7	0.5376 (5)	0.1878 (5)	0.1061 (3)	0.0634 (10)
H7A	0.6202	0.2993	0.1119	0.095*
H7B	0.5257	0.1806	0.0286	0.095*
H7C	0.6144	0.0775	0.1426	0.095*
C8	0.1737 (5)	0.0162 (5)	0.1638 (3)	0.0702 (11)
H8A	0.2552	−0.0899	0.2017	0.105*
H8B	0.1532	−0.0001	0.0884	0.105*
H8C	0.0299	0.0243	0.2023	0.105*
C9	0.1821 (5)	0.3734 (5)	0.1092 (3)	0.0662 (11)
H9A	0.0359	0.3771	0.1460	0.099*
H9B	0.1674	0.3714	0.0312	0.099*
H9C	0.2654	0.4835	0.1168	0.099*

	U11	U22	U33	U12	U13	U23
O1	0.117 (2)	0.095 (2)	0.0680 (19)	−0.0003 (17)	−0.0229 (17)	−0.0287 (16)
O2	0.0374 (12)	0.0691 (16)	0.0448 (14)	−0.0015 (10)	0.0004 (10)	−0.0143 (12)
O3	0.0360 (14)	0.139 (3)	0.0686 (18)	0.0020 (13)	−0.0019 (12)	−0.0330 (17)
N1	0.0523 (18)	0.064 (2)	0.0522 (19)	−0.0018 (13)	−0.0066 (14)	−0.0074 (15)
N2	0.0376 (15)	0.0592 (19)	0.0468 (18)	−0.0004 (12)	−0.0004 (14)	−0.0089 (14)
C1	0.057 (2)	0.046 (2)	0.049 (2)	−0.0062 (16)	0.0026 (18)	−0.0079 (17)
C2	0.0387 (18)	0.055 (2)	0.055 (2)	−0.0014 (15)	−0.0029 (16)	−0.0051 (19)
C3	0.0437 (19)	0.060 (2)	0.054 (2)	−0.0038 (16)	0.0089 (18)	−0.0105 (19)
C4	0.085 (3)	0.054 (3)	0.062 (3)	−0.007 (2)	−0.005 (2)	−0.013 (2)
C5	0.040 (2)	0.064 (2)	0.051 (2)	−0.0007 (16)	0.0038 (18)	−0.0114 (18)
C6	0.0434 (18)	0.058 (2)	0.041 (2)	0.0034 (16)	−0.0065 (15)	−0.0121 (17)
C7	0.047 (2)	0.086 (3)	0.057 (2)	−0.0012 (18)	0.0030 (17)	−0.016 (2)
C8	0.055 (2)	0.074 (3)	0.086 (3)	−0.0117 (19)	−0.0017 (19)	−0.026 (2)
C9	0.067 (2)	0.068 (3)	0.063 (3)	0.0089 (19)	−0.0101 (19)	−0.007 (2)

O1—C4	1.206 (4)	C4—H4	0.9300
O2—C5	1.315 (4)	C6—C9	1.512 (4)
O2—C6	1.501 (4)	C6—C8	1.518 (5)
O3—C5	1.196 (3)	C6—C7	1.519 (4)
N1—C2	1.301 (4)	C7—H7A	0.9600
N1—C1	1.398 (4)	C7—H7B	0.9600
N2—C3	1.376 (4)	C7—H7C	0.9600
N2—C2	1.378 (4)	C8—H8A	0.9600
N2—C5	1.417 (4)	C8—H8B	0.9600
C1—C3	1.356 (4)	C8—H8C	0.9600
C1—C4	1.464 (5)	C9—H9A	0.9600
C2—H2	0.9300	C9—H9B	0.9600
C3—H3	0.9300	C9—H9C	0.9600
C5—O2—C6	121.3 (2)	C9—C6—C8	113.1 (3)
C2—N1—C1	104.5 (3)	O2—C6—C7	102.4 (2)
C3—N2—C2	106.1 (3)	C9—C6—C7	110.8 (3)
C3—N2—C5	125.2 (3)	C8—C6—C7	111.5 (3)
C2—N2—C5	128.7 (3)	C6—C7—H7A	109.5
C3—C1—N1	110.6 (3)	C6—C7—H7B	109.5
C3—C1—C4	124.5 (3)	H7A—C7—H7B	109.5
N1—C1—C4	124.9 (3)	C6—C7—H7C	109.5
N1—C2—N2	112.7 (3)	H7A—C7—H7C	109.5
N1—C2—H2	123.6	H7B—C7—H7C	109.5
N2—C2—H2	123.6	C6—C8—H8A	109.5
C1—C3—N2	106.1 (3)	C6—C8—H8B	109.5
C1—C3—H3	126.9	H8A—C8—H8B	109.5
N2—C3—H3	126.9	C6—C8—H8C	109.5
O1—C4—C1	125.7 (4)	H8A—C8—H8C	109.5
O1—C4—H4	117.2	H8B—C8—H8C	109.5
C1—C4—H4	117.2	C6—C9—H9A	109.5
O3—C5—O2	129.1 (3)	C6—C9—H9B	109.5
O3—C5—N2	121.5 (3)	H9A—C9—H9B	109.5
O2—C5—N2	109.4 (3)	C6—C9—H9C	109.5
O2—C6—C9	109.5 (2)	H9A—C9—H9C	109.5
O2—C6—C8	109.0 (3)	H9B—C9—H9C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3i	0.93	2.36	3.251 (5)	160
C9—H9C···O1ii	0.96	2.65	3.531 (5)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3i	0.93	2.36	3.251 (5)	160
C9—H9C⋯O1ii	0.96	2.65	3.531 (5)	153

Symmetry codes: (i) ; (ii) .