1-Nitro-9H-carbazole.

In the title mol-ecule, C12H8N2O2, the nitro group is tilted slightly with respect to the carbazole moiety [angle between the least-squares planes = 4.43 (9)°]. In the crystal, the mol-ecules are connected via pairs of N-H⋯O hydrogen bonds into dimers with -1 symmetry. The dimers in turn are arranged into layers parallel to (10-1).

Related literature

For the applications of aryl­amines as electron donors, see: Shirota & Kageyama (2007 ▶); Tao et al. (2011 ▶); Yook & Lee (2012 ▶); Kautny et al. (2014 ▶). For the synthesis of the catalyst (NHC)Pd(all­yl)Cl, see: Marion et al. (2006 ▶).

Experimental

Crystal data

C12H8N2O2

M = 212.2

Monoclinic,

a = 10.4400 (3) Å

b = 5.3148 (2) Å

c = 17.2638 (6) Å

β = 99.7460 (16)°

V = 944.08 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.76 × 0.42 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.95, T max = 0.98

30130 measured reflections

2794 independent reflections

2397 reflections with I > 3σ(I)

R int = 0.021

Refinement

R[F 2 > 3σ(F 2)] = 0.040

wR(F 2) = 0.068

S = 1.89

2794 reflections

177 parameters

All H-atom parameters refined

Δρmax = 0.32 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT-Plus (Bruker, 2013 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ▶); molecular graphics: ATOMS (Dowty, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813032704/ff2123sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032704/ff2123Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813032704/ff2123Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C12H8N2O2	F(000) = 440
Mr = 212.2	Dx = 1.493 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 17802 reflections
a = 10.4400 (3) Å	θ = 2.4–30.1°
b = 5.3148 (2) Å	µ = 0.11 mm−1
c = 17.2638 (6) Å	T = 100 K
β = 99.7460 (16)°	Plate, dark yellow
V = 944.08 (6) Å3	0.76 × 0.42 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2794 independent reflections
Radiation source: X-ray tube	2397 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.021
ω and φ scans	θmax = 30.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −14→14
Tmin = 0.95, Tmax = 0.98	k = −7→7
30130 measured reflections	l = −24→24

Refinement on F	0 constraints
R[F2 > 2σ(F2)] = 0.040	All H-atom parameters refined
wR(F2) = 0.068	Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0009F2)
S = 1.89	(Δ/σ)max = 0.015
2794 reflections	Δρmax = 0.32 e Å−3
177 parameters	Δρmin = −0.21 e Å−3
0 restraints

	x	y	z	Uiso*/Ueq
O1	0.89295 (6)	0.40415 (13)	0.03186 (4)	0.0210 (2)
O2	0.72187 (8)	0.32391 (14)	0.08415 (4)	0.0262 (2)
N1	0.94574 (7)	0.15206 (14)	−0.09492 (4)	0.0148 (2)
N2	0.79470 (7)	0.27907 (15)	0.03678 (4)	0.0172 (2)
C1	0.84182 (8)	0.02688 (16)	−0.07504 (5)	0.0136 (2)
C2	0.76585 (8)	0.07065 (16)	−0.01702 (5)	0.0155 (2)
C3	0.66091 (8)	−0.08542 (18)	−0.01060 (5)	0.0190 (3)
C4	0.62951 (9)	−0.28368 (19)	−0.06284 (6)	0.0210 (3)
C5	0.70463 (9)	−0.33376 (17)	−0.12071 (6)	0.0184 (3)
C6	0.81094 (8)	−0.18269 (16)	−0.12662 (5)	0.0145 (2)
C7	0.90505 (8)	−0.17966 (16)	−0.17915 (5)	0.0148 (2)
C8	0.92934 (10)	−0.33696 (17)	−0.24006 (5)	0.0193 (3)
C9	1.03157 (10)	−0.27687 (19)	−0.27885 (6)	0.0226 (3)
C10	1.10889 (9)	−0.06296 (19)	−0.25785 (6)	0.0222 (3)
C11	1.08747 (9)	0.09238 (17)	−0.19688 (6)	0.0187 (3)
C12	0.98542 (8)	0.03034 (16)	−0.15802 (5)	0.0145 (2)
H11	1.1422 (11)	0.232 (3)	−0.1779 (8)	0.028 (3)*
H5	0.6817 (11)	−0.477 (2)	−0.1571 (7)	0.019 (3)*
H4	0.5546 (13)	−0.390 (2)	−0.0614 (8)	0.027 (3)*
H8	0.8730 (12)	−0.480 (2)	−0.2542 (8)	0.020 (3)*
H9	1.0526 (14)	−0.384 (3)	−0.3211 (10)	0.039 (4)*
H3	0.6077 (12)	−0.069 (2)	0.0296 (8)	0.026 (3)*
H10	1.1776 (11)	−0.026 (2)	−0.2858 (7)	0.018 (3)*
Hn1	0.9851 (12)	0.275 (3)	−0.0690 (9)	0.029 (3)*

	U11	U22	U33	U12	U13	U23
O1	0.0207 (3)	0.0221 (4)	0.0196 (3)	−0.0021 (3)	0.0017 (3)	−0.0039 (3)
O2	0.0301 (4)	0.0324 (4)	0.0187 (4)	0.0068 (3)	0.0117 (3)	−0.0020 (3)
N1	0.0153 (3)	0.0140 (4)	0.0157 (4)	−0.0019 (3)	0.0041 (3)	−0.0018 (3)
N2	0.0185 (4)	0.0198 (4)	0.0132 (4)	0.0041 (3)	0.0026 (3)	0.0014 (3)
C1	0.0124 (4)	0.0148 (4)	0.0133 (4)	0.0004 (3)	0.0010 (3)	0.0016 (3)
C2	0.0141 (4)	0.0184 (4)	0.0137 (4)	0.0018 (3)	0.0017 (3)	0.0012 (3)
C3	0.0138 (4)	0.0248 (5)	0.0187 (4)	0.0012 (3)	0.0033 (3)	0.0059 (3)
C4	0.0158 (4)	0.0226 (5)	0.0242 (5)	−0.0035 (3)	0.0018 (3)	0.0064 (4)
C5	0.0177 (4)	0.0170 (4)	0.0187 (4)	−0.0024 (3)	−0.0017 (3)	0.0033 (3)
C6	0.0149 (4)	0.0141 (4)	0.0135 (4)	0.0003 (3)	−0.0005 (3)	0.0014 (3)
C7	0.0163 (4)	0.0146 (4)	0.0127 (4)	0.0016 (3)	0.0007 (3)	0.0013 (3)
C8	0.0246 (5)	0.0171 (4)	0.0151 (4)	0.0053 (3)	−0.0001 (3)	−0.0013 (3)
C9	0.0279 (5)	0.0244 (5)	0.0160 (4)	0.0102 (4)	0.0053 (3)	0.0004 (3)
C10	0.0237 (4)	0.0246 (5)	0.0201 (4)	0.0095 (4)	0.0089 (3)	0.0064 (3)
C11	0.0177 (4)	0.0182 (4)	0.0215 (4)	0.0026 (3)	0.0067 (3)	0.0045 (3)
C12	0.0152 (4)	0.0140 (4)	0.0144 (4)	0.0024 (3)	0.0030 (3)	0.0018 (3)

O1—N2	1.2372 (11)	C5—C6	1.3875 (13)
O2—N2	1.2305 (12)	C5—H5	0.991 (11)
N1—C1	1.3651 (12)	C6—C7	1.4456 (13)
N1—C12	1.3890 (12)	C7—C8	1.3997 (13)
N1—Hn1	0.857 (13)	C7—C12	1.4068 (12)
N2—C2	1.4442 (11)	C8—C9	1.3898 (15)
C1—C2	1.3984 (13)	C8—H8	0.969 (13)
C1—C6	1.4283 (12)	C9—C10	1.4058 (14)
C2—C3	1.3935 (13)	C9—H9	0.981 (16)
C3—C4	1.3897 (14)	C10—C11	1.3854 (14)
C3—H3	0.964 (15)	C10—H10	0.951 (13)
C4—C5	1.3962 (15)	C11—C12	1.3914 (14)
C4—H4	0.967 (13)	C11—H11	0.960 (13)
C1—N1—C12	108.99 (7)	C1—C6—C5	120.29 (8)
C1—N1—Hn1	124.9 (10)	C1—C6—C7	106.06 (7)
C12—N1—Hn1	125.8 (10)	C5—C6—C7	133.60 (8)
O1—N2—O2	123.66 (8)	C6—C7—C8	133.90 (8)
O1—N2—C2	116.94 (8)	C6—C7—C12	106.56 (7)
O2—N2—C2	119.40 (8)	C8—C7—C12	119.52 (8)
N1—C1—C2	132.09 (8)	C7—C8—C9	118.44 (8)
N1—C1—C6	109.18 (8)	C7—C8—H8	118.6 (8)
C2—C1—C6	118.73 (8)	C9—C8—H8	122.9 (8)
N2—C2—C1	120.43 (8)	C8—C9—C10	121.06 (9)
N2—C2—C3	119.11 (8)	C8—C9—H9	120.8 (9)
C1—C2—C3	120.46 (8)	C10—C9—H9	118.1 (9)
C2—C3—C4	120.13 (9)	C9—C10—C11	121.22 (10)
C2—C3—H3	124.0 (7)	C9—C10—H10	119.1 (7)
C4—C3—H3	115.9 (7)	C11—C10—H10	119.7 (7)
C3—C4—C5	120.64 (9)	C10—C11—C12	117.41 (8)
C3—C4—H4	121.8 (9)	C10—C11—H11	123.9 (8)
C5—C4—H4	117.5 (9)	C12—C11—H11	118.6 (8)
C4—C5—C6	119.70 (8)	N1—C12—C7	109.20 (8)
C4—C5—H5	119.7 (7)	N1—C12—C11	128.47 (8)
C6—C5—H5	120.6 (7)	C7—C12—C11	122.32 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—Hn1···O1i	0.857 (13)	2.159 (13)	2.9940 (10)	164.6 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—Hn1⋯O1i	0.857 (13)	2.159 (13)	2.9940 (10)	164.6 (14)

Symmetry code: (i) .