5-Nitro-2-(piperidin-1-yl)benzaldehyde.

In the structure of the title compound, C(12)H(14)N(2)O(3), the piperidine ring adopts a chair conformation and the aryl substitutent occupies an equatorial position.

Related literature

For the toxicity of nitro­aromatics, see: Cronin et al. (1998 ▶); Shinoda et al. (1998 ▶). For piperidine ring conformations, see: Parkin et al. (2004 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶). For reference bond lengths, see: Allen et al. (1987 ▶) and for bond angles, see; Codding & Kerr (1978 ▶).

Experimental

Crystal data

C12H14N2O3

M = 234.25

Triclinic,

a = 5.686 (2) Å

b = 10.102 (5) Å

c = 10.221 (4) Å

α = 80.767 (2)°

β = 80.733 (3)°

γ = 86.034 (2)°

V = 571.4 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.30 × 0.25 × 0.25 mm

Data collection

Nonius KappaCCCD area-detector diffractometer

Absorption correction: none

11460 measured reflections

3280 independent reflections

2239 reflections with I > 2.0σ(I)

R int = 0.03

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.111

S = 1.02

2058 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.15 e Å−3

Data collection: COLLECT (Nonius, 1997 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: CRYSTALS.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809043700/ng2664sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043700/ng2664Isup2.hkl

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

C12H14N2O3	Z = 2
Mr = 234.25	F(000) = 248
Triclinic, P1	Dx = 1.362 Mg m−3
Hall symbol: -P 1	Melting point: 388 K
a = 5.686 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.102 (5) Å	Cell parameters from 3280 reflections
c = 10.221 (4) Å	θ = 2–30°
α = 80.767 (2)°	µ = 0.10 mm−1
β = 80.733 (3)°	T = 295 K
γ = 86.034 (2)°	Prism, orange
V = 571.4 (4) Å3	0.30 × 0.25 × 0.25 mm

Nonius KappaCCCD area detector diffractometer	Rint = 0.03
graphite	θmax = 30.2°, θmin = 2.0°
φ scans	h = 0→8
11460 measured reflections	k = −14→14
3280 independent reflections	l = −13→14
2239 reflections with I > 2.0σ(I)

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.111	Method = Modified Sheldrick w = 1/[σ2(F2) + ( 0.06P)2 + 0.1P] , where P = (max(Fo2,0) + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.0004
2058 reflections	Δρmax = 0.16 e Å−3
154 parameters	Δρmin = −0.15 e Å−3
0 restraints

Refinement. We had 3280 independent reflections but 2058 reflections were used in the refinement, instead of 3280 because the refinement was carried out under conditions I > 3σ(I).

	x	y	z	Uiso*/Ueq
N1	−0.2540 (2)	−0.19297 (12)	0.65442 (13)	0.0538
N2	0.1530 (2)	0.26552 (11)	0.75678 (11)	0.0494
C1	−0.1479 (2)	−0.07454 (13)	0.68028 (13)	0.0446
C2	0.0235 (2)	−0.08957 (12)	0.76296 (12)	0.0437
C3	0.1255 (2)	0.02260 (12)	0.78871 (12)	0.0421
C4	0.0534 (2)	0.15293 (12)	0.73040 (12)	0.0428
C5	−0.1174 (3)	0.16295 (13)	0.64329 (14)	0.0514
C6	−0.2181 (3)	0.05102 (14)	0.61906 (14)	0.0516
C7	0.3268 (3)	−0.00219 (15)	0.86587 (14)	0.0530
C8	0.1313 (3)	0.28678 (15)	0.89744 (13)	0.0539
C9	0.3194 (3)	0.37797 (17)	0.91473 (16)	0.0665
C10	0.3053 (4)	0.51042 (17)	0.82255 (17)	0.0676
C11	0.3178 (3)	0.48655 (15)	0.67935 (16)	0.0630
C12	0.1293 (3)	0.39255 (14)	0.66607 (15)	0.0573
O1	−0.1742 (2)	−0.30357 (10)	0.69841 (14)	0.0772
O2	−0.4183 (2)	−0.17831 (12)	0.58925 (14)	0.0796
O3	0.3735 (2)	−0.10961 (12)	0.92869 (13)	0.0761
H2	0.0775	−0.1770	0.8003	0.0524*
H5	−0.1691	0.2482	0.6013	0.0617*
H6	−0.3366	0.0604	0.5608	0.0619*
H7	0.4264	0.0706	0.8620	0.0636*
H81	0.1423	0.1992	0.9549	0.0647*
H82	−0.0258	0.3295	0.9232	0.0647*
H91	0.3019	0.3901	1.0089	0.0798*
H92	0.4712	0.3336	0.8926	0.0798*
H101	0.4289	0.5645	0.8298	0.0812*
H102	0.1507	0.5572	0.8515	0.0812*
H111	0.2952	0.5712	0.6206	0.0756*
H112	0.4750	0.4465	0.6503	0.0756*
H121	−0.0316	0.4328	0.6880	0.0688*
H122	0.1462	0.3734	0.5738	0.0688*

	U11	U22	U33	U12	U13	U23
N1	0.0571 (7)	0.0479 (7)	0.0585 (7)	−0.0037 (5)	−0.0156 (6)	−0.0069 (5)
N2	0.0716 (8)	0.0387 (5)	0.0387 (5)	−0.0033 (5)	−0.0132 (5)	−0.0032 (4)
C1	0.0483 (7)	0.0414 (7)	0.0447 (7)	−0.0017 (5)	−0.0089 (5)	−0.0067 (5)
C2	0.0490 (7)	0.0396 (6)	0.0400 (6)	0.0018 (5)	−0.0067 (5)	−0.0001 (5)
C3	0.0477 (7)	0.0415 (6)	0.0365 (6)	−0.0001 (5)	−0.0085 (5)	−0.0023 (5)
C4	0.0519 (7)	0.0396 (6)	0.0361 (6)	0.0001 (5)	−0.0066 (5)	−0.0043 (5)
C5	0.0636 (9)	0.0401 (7)	0.0508 (7)	0.0056 (6)	−0.0187 (6)	−0.0011 (5)
C6	0.0570 (8)	0.0492 (7)	0.0510 (7)	0.0025 (6)	−0.0204 (6)	−0.0044 (6)
C7	0.0565 (8)	0.0502 (8)	0.0527 (8)	−0.0027 (6)	−0.0168 (6)	−0.0006 (6)
C8	0.0693 (9)	0.0528 (8)	0.0409 (7)	−0.0078 (7)	−0.0078 (6)	−0.0093 (6)
C9	0.0804 (11)	0.0674 (10)	0.0576 (9)	−0.0135 (8)	−0.0267 (8)	−0.0066 (8)
C10	0.0807 (11)	0.0571 (9)	0.0718 (10)	−0.0192 (8)	−0.0251 (9)	−0.0094 (8)
C11	0.0770 (11)	0.0475 (8)	0.0622 (9)	−0.0086 (7)	−0.0112 (8)	0.0018 (7)
C12	0.0848 (11)	0.0394 (7)	0.0501 (8)	−0.0030 (7)	−0.0215 (7)	−0.0026 (6)
O1	0.0870 (8)	0.0420 (6)	0.1096 (10)	−0.0025 (5)	−0.0414 (7)	−0.0056 (6)
O2	0.0848 (8)	0.0650 (7)	0.1011 (10)	−0.0102 (6)	−0.0519 (8)	−0.0082 (7)
O3	0.0848 (8)	0.0595 (7)	0.0874 (9)	−0.0029 (6)	−0.0478 (7)	0.0128 (6)

N1—O1	1.2210 (16)	C1—C6	1.3839 (19)
N1—C1	1.4553 (18)	C6—H61	0.959
N1—O2	1.2195 (16)	C8—C9	1.507 (2)
C3—C4	1.4174 (17)	C8—H81	0.984
C3—C2	1.3878 (19)	C8—H82	0.980
C3—C7	1.4773 (19)	C12—C11	1.516 (2)
C4—N2	1.3868 (17)	C12—H122	0.981
C4—C5	1.4081 (19)	C12—H121	0.982
N2—C8	1.4720 (18)	C9—C10	1.513 (2)
N2—C12	1.4694 (17)	C9—H92	0.956
C5—C6	1.376 (2)	C9—H91	0.978
C5—H51	0.949	C11—C10	1.511 (2)
C2—C1	1.3750 (19)	C11—H112	0.977
C2—H21	0.955	C11—H111	0.977
C7—O3	1.2049 (18)	C10—H101	0.939
C7—H71	0.951	C10—H102	0.993
O1—N1—C1	118.62 (12)	C9—C8—H81	111.4
O1—N1—O2	122.42 (13)	N2—C8—H82	108.6
C1—N1—O2	118.96 (12)	C9—C8—H82	108.4
C4—C3—C2	120.29 (12)	H81—C8—H82	108.4
C4—C3—C7	122.63 (12)	N2—C12—C11	109.92 (13)
C2—C3—C7	116.75 (12)	N2—C12—H122	108.8
C3—C4—N2	120.58 (12)	C11—C12—H122	110.7
C3—C4—C5	117.61 (12)	N2—C12—H121	109.0
N2—C4—C5	121.79 (12)	C11—C12—H121	110.9
C4—N2—C8	118.01 (11)	H122—C12—H121	107.5
C4—N2—C12	118.40 (11)	C8—C9—C10	110.77 (14)
C8—N2—C12	111.78 (11)	C8—C9—H92	107.4
C4—C5—C6	121.51 (12)	C10—C9—H92	109.5
C4—C5—H51	120.3	C8—C9—H91	109.3
C6—C5—H51	118.1	C10—C9—H91	112.0
C3—C2—C1	119.98 (12)	H92—C9—H91	107.7
C3—C2—H21	119.5	C12—C11—C10	111.64 (13)
C1—C2—H21	120.4	C12—C11—H112	108.8
C3—C7—O3	123.42 (14)	C10—C11—H112	108.6
C3—C7—H71	117.1	C12—C11—H111	108.5
O3—C7—H71	119.4	C10—C11—H111	110.5
N1—C1—C2	119.43 (12)	H112—C11—H111	108.8
N1—C1—C6	119.35 (12)	C9—C10—C11	110.19 (14)
C2—C1—C6	121.20 (12)	C9—C10—H101	110.3
C1—C6—C5	119.35 (13)	C11—C10—H101	110.4
C1—C6—H61	120.6	C9—C10—H102	107.9
C5—C6—H61	120.1	C11—C10—H102	109.6
N2—C8—C9	110.88 (12)	H101—C10—H102	108.3
N2—C8—H81	109.1
C12—N2—C8—C9	−58.84 (17)	C8—C9—C10—C11	−54.06 (18)
C8—N2—C12—C11	58.21 (16)	C9—C10—C11—C12	54.45 (18)
N2—C8—C9—C10	56.24 (17)	C10—C11—C12—N2	−56.22 (17)