Stacking and N—H...O inter­actions in 2,3-dimeth­yl-6-nitro­aniline

The non-H atoms of the title compound, C₈H₁₀N₂O₂, are almost coplanar. The conformation is stabilized by an intra­molecular N—H...O hydrogen bond. The mol­ecules are linked via inter­molecular N—H...O hydrogen bonds into a one-dimensional chain. There are inter­molecular C—H...π inter­actions and π...π stacking inter­actions present in the structure. The hydrogen-bonded chain is expanded into a three-dimensional net via stacking inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.054
• wR factor = 0.163
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.47

Author Response: ... Because collected data were relatively weak, there is a small amount of reflections with very high measured standard uncertainties of the squared structure factors, and a part of reflections was marked as unobserved and excluded from the data set by diffractometer data reduction software. This affect fraction of unique reflections observed.

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....        H2A
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....        H2B
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1     -   N1      ..       5.57 su

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CrysAlis CCD (UNIL IC & Kuma, 2000); cell refinement: CrysAlis RED (UNIL IC & Kuma, 2000); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Mercury (Version 1.4; Bruno et al., 2002); software used to prepare material for publication: SHELXL97.

2,3-dimethyl-6-nitroaniline

Crystal data

C8H10N2O2	F(000) = 704
Mr = 166.18	Dx = 1.349 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.4439 (11) Å	Cell parameters from 5030 reflections
b = 8.6837 (6) Å	θ = 2–25°
c = 14.0031 (10) Å	µ = 0.10 mm^−1
β = 111.251 (9)°	T = 291 K
V = 1636.9 (2) Å^3	Prism, orange
Z = 8	0.48 × 0.40 × 0.25 mm

Data collection

Kuma KM-4 CCD diffractometer	1492 independent reflections
Radiation source: fine-focus sealed tube	1297 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ω scans	θmax = 25.3°, θmin = 2.8°
Absorption correction: numerical (X-RED; Stoe & Cie, 1999)	h = −17→17
Tmin = 0.941, Tmax = 0.991	k = −10→10
9090 measured reflections	l = −16→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: difference Fourier map
wR(F^2) = 0.163	H-atom parameters constrained
S = 1.17	w = 1/[σ^2(Fo^2) + (0.0975P)^2 + 0.2133P] where P = (Fo^2 + 2Fc^2)/3
1492 reflections	(Δ/σ)max < 0.001
112 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.19 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
C1	0.38107 (12)	0.80506 (19)	0.07627 (12)	0.0371 (4)
C2	0.38012 (12)	0.81245 (18)	−0.02559 (12)	0.0353 (4)
C3	0.37547 (12)	0.67001 (18)	−0.07882 (13)	0.0368 (4)
C4	0.36957 (12)	0.53156 (18)	−0.03186 (13)	0.0396 (5)
C5	0.37129 (14)	0.5295 (2)	0.06996 (15)	0.0482 (5)
H5	0.3684	0.4360	0.1012	0.058*
C6	0.37709 (14)	0.6637 (2)	0.12263 (14)	0.0456 (5)
H6	0.3784	0.6612	0.1895	0.055*
N1	0.38383 (11)	0.94163 (18)	0.13640 (12)	0.0474 (4)
O1	0.38809 (11)	1.07134 (16)	0.10086 (12)	0.0652 (5)
O2	0.38082 (12)	0.92551 (18)	0.22332 (11)	0.0677 (5)
N2	0.38212 (11)	0.94697 (17)	−0.07443 (12)	0.0498 (5)
H2A	0.38409 (12)	1.0347 (18)	−0.0432 (6)	0.060*
H2B	0.38142 (12)	0.94573 (17)	−0.1371 (12)	0.060*
C7	0.37622 (17)	0.6753 (2)	−0.18646 (14)	0.0559 (6)
H7A	0.3853	0.5732	−0.2078	0.084*
H7B	0.4296	0.7401	−0.1878	0.084*
H7C	0.3142	0.7161	−0.2321	0.084*
C8	0.36032 (16)	0.3797 (2)	−0.08706 (16)	0.0564 (5)
H8A	0.4199	0.3605	−0.1006	0.085*
H8B	0.3046	0.3834	−0.1506	0.085*
H8C	0.3507	0.2985	−0.0451	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0406 (9)	0.0395 (9)	0.0331 (9)	0.0016 (6)	0.0155 (7)	−0.0038 (7)
C2	0.0363 (8)	0.0362 (9)	0.0343 (9)	0.0034 (6)	0.0140 (7)	0.0012 (6)
C3	0.0407 (9)	0.0373 (9)	0.0321 (8)	0.0057 (6)	0.0127 (7)	−0.0013 (6)
C4	0.0426 (9)	0.0360 (10)	0.0390 (10)	0.0036 (6)	0.0133 (7)	0.0002 (7)
C5	0.0619 (11)	0.0401 (10)	0.0458 (11)	0.0038 (8)	0.0233 (9)	0.0096 (8)
C6	0.0589 (11)	0.0495 (11)	0.0329 (9)	0.0040 (8)	0.0220 (8)	0.0037 (7)
N1	0.0513 (9)	0.0498 (9)	0.0440 (9)	−0.0005 (7)	0.0205 (7)	−0.0127 (7)
O1	0.0947 (11)	0.0398 (8)	0.0712 (10)	−0.0049 (7)	0.0422 (8)	−0.0119 (6)
O2	0.0944 (12)	0.0747 (10)	0.0433 (8)	−0.0013 (8)	0.0362 (8)	−0.0161 (7)
N2	0.0736 (11)	0.0372 (8)	0.0461 (9)	−0.0008 (7)	0.0305 (8)	0.0031 (6)
C7	0.0828 (15)	0.0515 (11)	0.0369 (10)	0.0074 (9)	0.0259 (10)	0.0006 (8)
C8	0.0697 (12)	0.0383 (10)	0.0610 (12)	0.0036 (9)	0.0234 (10)	−0.0059 (9)

Geometric parameters (Å, º)

C1—C6	1.399 (2)	C6—H6	0.9300
C1—C2	1.423 (2)	N1—O2	1.241 (2)
C1—N1	1.447 (2)	N1—O1	1.242 (2)
C2—N2	1.359 (2)	N2—H2A	0.8742
C2—C3	1.433 (2)	N2—H2B	0.8742
C3—C4	1.388 (2)	C7—H7A	0.9600
C3—C7	1.512 (2)	C7—H7B	0.9600
C4—C5	1.417 (3)	C7—H7C	0.9600
C4—C8	1.510 (2)	C8—H8A	0.9600
C5—C6	1.365 (2)	C8—H8B	0.9600
C5—H5	0.9300	C8—H8C	0.9600
C6—C1—C2	121.16 (14)	O2—N1—O1	121.30 (15)
C6—C1—N1	116.49 (15)	O2—N1—C1	118.35 (15)
C2—C1—N1	122.33 (15)	O1—N1—C1	120.34 (15)
N2—C2—C1	123.29 (14)	C2—N2—H2A	120.0
N2—C2—C3	119.06 (14)	C2—N2—H2B	120.0
C1—C2—C3	117.65 (14)	H2A—N2—H2B	120.0
C4—C3—C2	120.05 (15)	C3—C7—H7A	109.5
C4—C3—C7	121.51 (15)	C3—C7—H7B	109.5
C2—C3—C7	118.44 (14)	H7A—C7—H7B	109.5
C3—C4—C5	120.38 (15)	C3—C7—H7C	109.5
C3—C4—C8	121.56 (16)	H7A—C7—H7C	109.5
C5—C4—C8	118.06 (15)	H7B—C7—H7C	109.5
C6—C5—C4	120.56 (15)	C4—C8—H8A	109.5
C6—C5—H5	119.7	C4—C8—H8B	109.5
C4—C5—H5	119.7	H8A—C8—H8B	109.5
C5—C6—C1	120.18 (16)	C4—C8—H8C	109.5
C5—C6—H6	119.9	H8A—C8—H8C	109.5
C1—C6—H6	119.9	H8B—C8—H8C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.87	2.02	2.654 (2)	128
N2—H2B···O2^i	0.87	2.25	3.035 (2)	150
C6—H6···O2	0.93	2.34	2.665 (2)	100

Symmetry code: (i) x, −y+2, z−1/2.