1-(2-Nitro-benz-yl)-1H-pyrrole-2-carbaldehyde.

In the title compound, C(12)H(10)N(2)O(3), the five- and six-membered rings form a dihedral angle of 83.96 (6)°. The nitro group is twisted by 5.92 (8)° from the plane of the attached benzene ring. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into columns in the [100] direction, with a short distance of 3.725 (3) Å between the centroids of benzene rings inside these columns.

Related literature

The title compound is an inter­mediate in the synthesis of lixivaptan (systematic name N-[3-chloro-4-(5H-pyrrolo-[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbon­yl)phen­yl]-5-fluoro-2-methyl­benzamide), a vasopressin receptor antagonist with high V2 receptor affinity. For preliminary studies of lixivaptan, which is now undergoing Phase III clinical trials, see, for example, Ku et al. (2009 ▶). For the synthesis of the title compound, see: Albright et al. (1998 ▶).

Experimental

Crystal data

C12H10N2O3

M = 230.22

Triclinic,

a = 7.2643 (8) Å

b = 8.3072 (10) Å

c = 9.2570 (12) Å

α = 104.10 (2)°

β = 96.463 (11)°

γ = 96.92 (2)°

V = 531.98 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 113 K

0.20 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.979, T max = 0.990

6867 measured reflections

2544 independent reflections

1517 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.095

S = 0.95

2544 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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/S1600536811018459/cv5092sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018459/cv5092Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811018459/cv5092Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536811018459/cv5092Isup4.cml

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

C12H10N2O3	Z = 2
Mr = 230.22	F(000) = 240
Triclinic, P1	Dx = 1.437 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2643 (8) Å	Cell parameters from 1889 reflections
b = 8.3072 (10) Å	θ = 2.3–28.0°
c = 9.2570 (12) Å	µ = 0.11 mm−1
α = 104.10 (2)°	T = 113 K
β = 96.463 (11)°	Prism, colourless
γ = 96.92 (2)°	0.20 × 0.18 × 0.10 mm
V = 531.98 (11) Å3

Rigaku Saturn CCD area-detector diffractometer	2544 independent reflections
Radiation source: rotating anode	1517 reflections with I > 2σ(I)
multilayer	Rint = 0.040
Detector resolution: 14.22 pixels mm-1	θmax = 28.0°, θmin = 2.3°
ω and φ scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −10→10
Tmin = 0.979, Tmax = 0.990	l = −12→12
6867 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0455P)2] where P = (Fo2 + 2Fc2)/3
2544 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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
O1	0.73782 (17)	0.83214 (12)	0.55982 (12)	0.0507 (4)
O2	0.80539 (16)	0.77297 (12)	0.33569 (12)	0.0402 (3)
O3	0.39124 (13)	0.35491 (12)	0.08896 (11)	0.0281 (2)
N1	0.76728 (15)	0.73149 (14)	0.44833 (13)	0.0255 (3)
N2	0.78470 (15)	0.30999 (13)	0.04974 (12)	0.0206 (3)
C1	0.75954 (17)	0.55405 (15)	0.45094 (15)	0.0202 (3)
C2	0.73377 (18)	0.52045 (17)	0.58762 (15)	0.0258 (3)
H2	0.7209	0.6085	0.6714	0.031*
C3	0.72705 (19)	0.35811 (18)	0.60071 (16)	0.0291 (3)
H3	0.7088	0.3334	0.6935	0.035*
C4	0.74712 (19)	0.23132 (17)	0.47785 (16)	0.0284 (3)
H4	0.7449	0.1196	0.4869	0.034*
C5	0.77038 (18)	0.26669 (16)	0.34158 (16)	0.0244 (3)
H5	0.7827	0.1777	0.2583	0.029*
C6	0.77633 (17)	0.42904 (16)	0.32299 (14)	0.0198 (3)
C7	0.79970 (19)	0.46275 (15)	0.17131 (14)	0.0220 (3)
H7A	0.7028	0.5293	0.1451	0.026*
H7B	0.9238	0.5311	0.1800	0.026*
C8	0.93194 (19)	0.24383 (17)	−0.00619 (15)	0.0251 (3)
H8	1.0605	0.2868	0.0300	0.030*
C9	0.86490 (19)	0.10454 (17)	−0.12366 (15)	0.0275 (3)
H9	0.9382	0.0351	−0.1829	0.033*
C10	0.66954 (19)	0.08388 (15)	−0.14002 (15)	0.0237 (3)
H10	0.5857	−0.0025	−0.2124	0.028*
C11	0.61976 (18)	0.21166 (15)	−0.03203 (14)	0.0200 (3)
C12	0.43411 (19)	0.24082 (17)	−0.00666 (15)	0.0226 (3)
H12	0.3335	0.1635	−0.0708	0.027*

	U11	U22	U33	U12	U13	U23
O1	0.0839 (10)	0.0285 (6)	0.0404 (7)	0.0147 (6)	0.0260 (7)	−0.0002 (5)
O2	0.0676 (8)	0.0260 (6)	0.0292 (6)	0.0057 (5)	0.0086 (6)	0.0110 (5)
O3	0.0241 (5)	0.0363 (6)	0.0267 (6)	0.0097 (4)	0.0074 (4)	0.0094 (5)
N1	0.0252 (6)	0.0239 (6)	0.0257 (7)	0.0043 (5)	0.0009 (5)	0.0042 (5)
N2	0.0180 (6)	0.0239 (6)	0.0197 (6)	0.0037 (5)	0.0028 (5)	0.0054 (5)
C1	0.0153 (6)	0.0201 (7)	0.0250 (8)	0.0017 (5)	0.0001 (5)	0.0072 (6)
C2	0.0202 (7)	0.0340 (8)	0.0216 (8)	0.0021 (6)	0.0024 (6)	0.0056 (6)
C3	0.0245 (8)	0.0399 (9)	0.0249 (8)	0.0001 (7)	0.0004 (6)	0.0160 (7)
C4	0.0248 (8)	0.0274 (7)	0.0355 (9)	−0.0001 (6)	−0.0011 (6)	0.0172 (7)
C5	0.0226 (7)	0.0222 (7)	0.0273 (8)	0.0024 (6)	0.0001 (6)	0.0068 (6)
C6	0.0139 (6)	0.0229 (7)	0.0222 (7)	0.0020 (5)	0.0002 (5)	0.0065 (6)
C7	0.0236 (7)	0.0212 (7)	0.0203 (7)	0.0016 (6)	0.0019 (6)	0.0051 (6)
C8	0.0178 (7)	0.0332 (8)	0.0273 (8)	0.0065 (6)	0.0060 (6)	0.0114 (6)
C9	0.0295 (8)	0.0315 (8)	0.0260 (8)	0.0123 (6)	0.0098 (6)	0.0095 (6)
C10	0.0270 (7)	0.0225 (7)	0.0210 (7)	0.0017 (6)	0.0028 (6)	0.0058 (6)
C11	0.0192 (7)	0.0234 (7)	0.0183 (7)	0.0023 (5)	0.0020 (5)	0.0082 (5)
C12	0.0205 (7)	0.0278 (7)	0.0215 (7)	0.0024 (6)	0.0014 (6)	0.0116 (6)

O1—N1	1.2175 (14)	C4—H4	0.9500
O2—N1	1.2247 (14)	C5—C6	1.3968 (18)
O3—C12	1.2260 (15)	C5—H5	0.9500
N1—C1	1.4745 (16)	C6—C7	1.5207 (17)
N2—C8	1.3571 (16)	C7—H7A	0.9900
N2—C11	1.3909 (16)	C7—H7B	0.9900
N2—C7	1.4602 (15)	C8—C9	1.3750 (19)
C1—C2	1.3881 (17)	C8—H8	0.9500
C1—C6	1.4000 (18)	C9—C10	1.3952 (18)
C2—C3	1.3787 (19)	C9—H9	0.9500
C2—H2	0.9500	C10—C11	1.3834 (17)
C3—C4	1.3837 (19)	C10—H10	0.9500
C3—H3	0.9500	C11—C12	1.4335 (17)
C4—C5	1.3867 (18)	C12—H12	0.9500
O1—N1—O2	122.35 (12)	C1—C6—C7	123.58 (11)
O1—N1—C1	118.45 (12)	N2—C7—C6	113.43 (10)
O2—N1—C1	119.20 (11)	N2—C7—H7A	108.9
C8—N2—C11	108.47 (11)	C6—C7—H7A	108.9
C8—N2—C7	125.06 (11)	N2—C7—H7B	108.9
C11—N2—C7	126.43 (10)	C6—C7—H7B	108.9
C2—C1—C6	122.84 (12)	H7A—C7—H7B	107.7
C2—C1—N1	115.52 (12)	N2—C8—C9	108.95 (12)
C6—C1—N1	121.64 (12)	N2—C8—H8	125.5
C3—C2—C1	119.42 (13)	C9—C8—H8	125.5
C3—C2—H2	120.3	C8—C9—C10	107.48 (12)
C1—C2—H2	120.3	C8—C9—H9	126.3
C2—C3—C4	119.60 (13)	C10—C9—H9	126.3
C2—C3—H3	120.2	C11—C10—C9	107.74 (12)
C4—C3—H3	120.2	C11—C10—H10	126.1
C3—C4—C5	120.23 (13)	C9—C10—H10	126.1
C3—C4—H4	119.9	C10—C11—N2	107.36 (11)
C5—C4—H4	119.9	C10—C11—C12	127.39 (13)
C4—C5—C6	122.05 (13)	N2—C11—C12	125.25 (12)
C4—C5—H5	119.0	O3—C12—C11	126.96 (13)
C6—C5—H5	119.0	O3—C12—H12	116.5
C5—C6—C1	115.84 (12)	C11—C12—H12	116.5
C5—C6—C7	120.58 (12)
O1—N1—C1—C2	−5.10 (18)	C11—N2—C7—C6	82.11 (15)
O2—N1—C1—C2	173.91 (12)	C5—C6—C7—N2	9.06 (17)
O1—N1—C1—C6	174.59 (12)	C1—C6—C7—N2	−170.91 (11)
O2—N1—C1—C6	−6.41 (19)	C11—N2—C8—C9	0.35 (14)
C6—C1—C2—C3	1.07 (19)	C7—N2—C8—C9	−177.37 (12)
N1—C1—C2—C3	−179.24 (11)	N2—C8—C9—C10	−0.30 (15)
C1—C2—C3—C4	0.36 (19)	C8—C9—C10—C11	0.14 (15)
C2—C3—C4—C5	−1.2 (2)	C9—C10—C11—N2	0.08 (14)
C3—C4—C5—C6	0.6 (2)	C9—C10—C11—C12	179.91 (12)
C4—C5—C6—C1	0.72 (19)	C8—N2—C11—C10	−0.26 (14)
C4—C5—C6—C7	−179.26 (12)	C7—N2—C11—C10	177.42 (11)
C2—C1—C6—C5	−1.58 (19)	C8—N2—C11—C12	179.89 (12)
N1—C1—C6—C5	178.76 (11)	C7—N2—C11—C12	−2.4 (2)
C2—C1—C6—C7	178.40 (12)	C10—C11—C12—O3	−179.65 (12)
N1—C1—C6—C7	−1.26 (19)	N2—C11—C12—O3	0.2 (2)
C8—N2—C7—C6	−100.58 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3i	0.95	2.41	3.1919 (17)	139
C8—H8···O3ii	0.95	2.37	3.3107 (17)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3i	0.95	2.41	3.1919 (17)	139
C8—H8⋯O3ii	0.95	2.37	3.3107 (17)	170

Symmetry codes: (i) ; (ii) .