2-Methyl-6-nitro­aniline

In the crystal structure of the title compound, C₇H₈N₂O₂, the mol­ecules are linked through N—H...O and N—H...N hydrogen bonds, forming an extended supramolecule, which contributes to the stability of the structure in the solid state. There are two molecules in the asymmetric unit.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.037
• wR factor = 0.107
• Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O3     -   N3      ..       6.58 su
PLAT353_ALERT_3_C Long    N-H Bond (0.87A)   N4     -   H4A    ...       1.02 Ang.
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C8

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

2-Methyl-6-nitroaniline

Crystal data

C7H8N2O2	F(000) = 640
Mr = 152.15	Dx = 1.380 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2333 reflections
a = 8.9844 (16) Å	θ = 2.9–23.4°
b = 11.359 (2) Å	µ = 0.10 mm^−1
c = 14.785 (3) Å	T = 294 K
β = 103.814 (2)°	Block, yellow
V = 1465.1 (5) Å^3	0.22 × 0.16 × 0.14 mm
Z = 8

Data collection

Bruker SMART CCD area-detector diffractometer	2589 independent reflections
Radiation source: fine-focus sealed tube	1931 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
Tmin = 0.968, Tmax = 0.986	k = −13→13
7772 measured reflections	l = −15→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0597P)^2 + 0.1509P] where P = (Fo^2 + 2Fc^2)/3
2589 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.11 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.28792 (14)	0.54144 (11)	0.41093 (8)	0.0733 (4)
O2	0.37257 (15)	0.56793 (12)	0.55800 (8)	0.0800 (4)
O3	0.8289 (2)	0.99462 (14)	0.60405 (10)	0.1025 (5)
O4	0.64899 (17)	0.87510 (15)	0.61259 (9)	0.0954 (5)
N1	0.28697 (15)	0.51650 (11)	0.49186 (9)	0.0551 (3)
N2	0.25384 (19)	0.45531 (14)	0.67751 (10)	0.0657 (4)
H2A	0.325 (2)	0.5098 (17)	0.6686 (14)	0.088 (6)*
H2B	0.246 (2)	0.4356 (18)	0.7308 (16)	0.093 (7)*
N3	0.72369 (18)	0.93022 (13)	0.56607 (10)	0.0694 (4)
N4	0.48473 (19)	0.77306 (16)	0.46317 (12)	0.0755 (5)
H4A	0.515 (3)	0.776 (2)	0.5342 (18)	0.127 (8)*
H4B	0.425 (2)	0.7185 (16)	0.4276 (13)	0.076 (6)*
C1	0.0331 (2)	0.29133 (16)	0.70392 (11)	0.0688 (5)
H1A	−0.0453	0.2325	0.6986	0.103*
H1B	0.0024	0.3614	0.7309	0.103*
H1C	0.1270	0.2623	0.7429	0.103*
C2	0.05660 (17)	0.31901 (12)	0.60917 (10)	0.0502 (4)
C3	0.16933 (16)	0.40320 (12)	0.60046 (9)	0.0453 (3)
C4	0.18314 (15)	0.42848 (12)	0.50911 (9)	0.0452 (3)
C5	0.09387 (18)	0.37194 (13)	0.43156 (10)	0.0550 (4)
H5	0.1064	0.3897	0.3724	0.066*
C6	−0.0115 (2)	0.29084 (14)	0.44216 (11)	0.0639 (4)
H6	−0.0713	0.2524	0.3906	0.077*
C7	−0.02885 (19)	0.26593 (13)	0.53135 (12)	0.0607 (4)
H7	−0.1019	0.2107	0.5380	0.073*
C8	0.4243 (2)	0.75291 (17)	0.26788 (13)	0.0776 (5)
H8A	0.4214	0.7584	0.2027	0.116*
H8B	0.3266	0.7756	0.2780	0.116*
H8C	0.4467	0.6733	0.2885	0.116*
C9	0.54645 (16)	0.83340 (13)	0.32171 (10)	0.0514 (4)
C10	0.63353 (17)	0.89972 (14)	0.27732 (11)	0.0579 (4)
H10	0.6151	0.8953	0.2128	0.069*
C11	0.74836 (19)	0.97342 (14)	0.32481 (12)	0.0628 (4)
H11	0.8065	1.0170	0.2925	0.075*
C12	0.77552 (19)	0.98172 (13)	0.41864 (12)	0.0602 (4)
H12	0.8529	1.0308	0.4511	0.072*
C13	0.68729 (17)	0.91653 (13)	0.46679 (10)	0.0514 (4)
C14	0.57157 (16)	0.83944 (12)	0.42012 (10)	0.0496 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0855 (9)	0.0889 (9)	0.0522 (7)	−0.0110 (7)	0.0299 (6)	0.0102 (6)
O2	0.0809 (8)	0.0968 (9)	0.0590 (7)	−0.0363 (7)	0.0103 (6)	0.0030 (7)
O3	0.1262 (13)	0.1014 (11)	0.0636 (9)	−0.0324 (10)	−0.0095 (8)	−0.0131 (7)
O4	0.1006 (10)	0.1383 (13)	0.0502 (7)	−0.0117 (9)	0.0235 (7)	0.0033 (8)
N1	0.0574 (8)	0.0626 (8)	0.0474 (8)	−0.0022 (6)	0.0170 (6)	0.0054 (6)
N2	0.0795 (10)	0.0767 (10)	0.0375 (8)	−0.0159 (8)	0.0075 (7)	0.0047 (7)
N3	0.0793 (10)	0.0752 (10)	0.0502 (8)	0.0042 (8)	0.0088 (8)	0.0003 (7)
N4	0.0739 (10)	0.0901 (11)	0.0644 (10)	−0.0252 (9)	0.0205 (8)	0.0114 (9)
C1	0.0792 (12)	0.0713 (11)	0.0634 (11)	−0.0009 (9)	0.0320 (9)	0.0128 (8)
C2	0.0582 (9)	0.0451 (8)	0.0507 (9)	0.0070 (7)	0.0198 (7)	0.0060 (6)
C3	0.0492 (8)	0.0463 (8)	0.0403 (8)	0.0067 (6)	0.0103 (6)	0.0035 (6)
C4	0.0500 (8)	0.0451 (8)	0.0423 (8)	0.0038 (6)	0.0143 (6)	0.0025 (6)
C5	0.0693 (10)	0.0546 (9)	0.0421 (8)	0.0038 (8)	0.0152 (7)	−0.0036 (7)
C6	0.0767 (11)	0.0580 (9)	0.0542 (10)	−0.0079 (8)	0.0101 (8)	−0.0128 (8)
C7	0.0666 (10)	0.0488 (8)	0.0691 (11)	−0.0077 (7)	0.0208 (9)	−0.0040 (8)
C8	0.0716 (11)	0.0872 (13)	0.0674 (11)	−0.0170 (10)	0.0034 (9)	−0.0056 (10)
C9	0.0489 (8)	0.0542 (8)	0.0490 (9)	0.0005 (7)	0.0075 (7)	0.0030 (7)
C10	0.0616 (10)	0.0669 (10)	0.0453 (8)	0.0037 (8)	0.0130 (7)	0.0099 (7)
C11	0.0663 (10)	0.0626 (10)	0.0623 (10)	−0.0068 (8)	0.0205 (8)	0.0158 (8)
C12	0.0610 (10)	0.0501 (9)	0.0665 (11)	−0.0092 (7)	0.0092 (8)	0.0034 (7)
C13	0.0573 (9)	0.0509 (8)	0.0442 (8)	0.0034 (7)	0.0086 (7)	0.0020 (6)
C14	0.0491 (8)	0.0517 (8)	0.0492 (9)	0.0026 (7)	0.0138 (7)	0.0087 (6)

Geometric parameters (Å, º)

O1—N1	1.2316 (17)	C4—C5	1.390 (2)
O2—N1	1.2368 (17)	C5—C6	1.357 (2)
O3—N3	1.2208 (19)	C5—H5	0.9300
O4—N3	1.2393 (19)	C6—C7	1.393 (2)
N1—C4	1.4312 (18)	C6—H6	0.9300
N2—C3	1.346 (2)	C7—H7	0.9300
N2—H2A	0.92 (2)	C8—C9	1.502 (2)
N2—H2B	0.84 (2)	C8—H8A	0.9600
N3—C13	1.434 (2)	C8—H8B	0.9600
N4—C14	1.349 (2)	C8—H8C	0.9600
N4—H4A	1.02 (3)	C9—C10	1.362 (2)
N4—H4B	0.902 (19)	C9—C14	1.420 (2)
C1—C2	1.499 (2)	C10—C11	1.383 (2)
C1—H1A	0.9600	C10—H10	0.9300
C1—H1B	0.9600	C11—C12	1.353 (2)
C1—H1C	0.9600	C11—H11	0.9300
C2—C7	1.362 (2)	C12—C13	1.397 (2)
C2—C3	1.421 (2)	C12—H12	0.9300
C3—C4	1.4149 (19)	C13—C14	1.408 (2)
O1—N1—O2	120.81 (13)	C5—C6—C7	119.08 (15)
O1—N1—C4	119.33 (13)	C5—C6—H6	120.5
O2—N1—C4	119.86 (12)	C7—C6—H6	120.5
C3—N2—H2A	116.4 (13)	C2—C7—C6	122.81 (15)
C3—N2—H2B	121.4 (14)	C2—C7—H7	118.6
H2A—N2—H2B	122.0 (19)	C6—C7—H7	118.6
O3—N3—O4	120.65 (15)	C9—C8—H8A	109.5
O3—N3—C13	119.87 (16)	C9—C8—H8B	109.5
O4—N3—C13	119.47 (15)	H8A—C8—H8B	109.5
C14—N4—H4A	115.3 (14)	C9—C8—H8C	109.5
C14—N4—H4B	116.0 (12)	H8A—C8—H8C	109.5
H4A—N4—H4B	126.7 (18)	H8B—C8—H8C	109.5
C2—C1—H1A	109.5	C10—C9—C14	119.86 (14)
C2—C1—H1B	109.5	C10—C9—C8	120.83 (15)
H1A—C1—H1B	109.5	C14—C9—C8	119.31 (14)
C2—C1—H1C	109.5	C9—C10—C11	122.33 (15)
H1A—C1—H1C	109.5	C9—C10—H10	118.8
H1B—C1—H1C	109.5	C11—C10—H10	118.8
C7—C2—C3	119.44 (13)	C12—C11—C10	119.52 (15)
C7—C2—C1	121.31 (14)	C12—C11—H11	120.2
C3—C2—C1	119.24 (14)	C10—C11—H11	120.2
N2—C3—C4	123.94 (14)	C11—C12—C13	119.99 (15)
N2—C3—C2	119.31 (14)	C11—C12—H12	120.0
C4—C3—C2	116.74 (13)	C13—C12—H12	120.0
C5—C4—C3	121.93 (13)	C12—C13—C14	121.50 (14)
C5—C4—N1	116.63 (12)	C12—C13—N3	116.46 (14)
C3—C4—N1	121.42 (13)	C14—C13—N3	122.03 (14)
C6—C5—C4	119.98 (14)	N4—C14—C13	124.00 (15)
C6—C5—H5	120.0	N4—C14—C9	119.23 (15)
C4—C5—H5	120.0	C13—C14—C9	116.77 (13)
C7—C2—C3—N2	−179.85 (14)	C14—C9—C10—C11	0.5 (2)
C1—C2—C3—N2	0.8 (2)	C8—C9—C10—C11	−179.06 (16)
C7—C2—C3—C4	1.3 (2)	C9—C10—C11—C12	−0.7 (3)
C1—C2—C3—C4	−178.07 (13)	C10—C11—C12—C13	−0.3 (3)
N2—C3—C4—C5	179.65 (14)	C11—C12—C13—C14	1.4 (2)
C2—C3—C4—C5	−1.6 (2)	C11—C12—C13—N3	179.88 (15)
N2—C3—C4—N1	−2.3 (2)	O3—N3—C13—C12	−1.3 (2)
C2—C3—C4—N1	176.52 (12)	O4—N3—C13—C12	179.67 (15)
O1—N1—C4—C5	3.1 (2)	O3—N3—C13—C14	177.17 (16)
O2—N1—C4—C5	−178.11 (14)	O4—N3—C13—C14	−1.9 (2)
O1—N1—C4—C3	−175.05 (13)	C12—C13—C14—N4	178.90 (16)
O2—N1—C4—C3	3.7 (2)	N3—C13—C14—N4	0.5 (2)
C3—C4—C5—C6	0.8 (2)	C12—C13—C14—C9	−1.5 (2)
N1—C4—C5—C6	−177.38 (14)	N3—C13—C14—C9	−179.88 (13)
C4—C5—C6—C7	0.3 (2)	C10—C9—C14—N4	−179.85 (15)
C3—C2—C7—C6	−0.3 (2)	C8—C9—C14—N4	−0.3 (2)
C1—C2—C7—C6	179.04 (15)	C10—C9—C14—C13	0.5 (2)
C5—C6—C7—C2	−0.5 (3)	C8—C9—C14—C13	−179.87 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···O1	0.902 (19)	2.341 (19)	3.161 (2)	151.2 (16)
N4—H4A···O4	1.02 (3)	1.84 (2)	2.616 (2)	130 (2)
N2—H2B···O4^i	0.84 (2)	2.38 (2)	3.151 (2)	152.6 (18)
N2—H2A···N1	0.92 (2)	2.55 (2)	2.915 (2)	103.8 (14)
N2—H2A···O2	0.92 (2)	1.90 (2)	2.607 (2)	131.4 (17)

Symmetry code: (i) −x+1, y−1/2, −z+3/2.