N-tert-Butyl-4-chloro-5-methyl-2-nitro­aniline

The title compound, C₁₁H₁₅ClN₂O₂, lies on a crystallographic mirror plane of symmetry; thus all of its atoms, except for two of the tert-butyl methyl C atoms and the H atoms, are exactly coplanar. There is an intramolecular hydrogen bond between the amide N atom and a nitro O atom. There are no exceptionally close intermolecular contacts, but the planar portions of the mol­ecules stack with their planes only 3.39 Å apart.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.098
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ......         C7

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); 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.

N-tert-Butyl-4-chloro-5-methyl-2-nitroaniline

Crystal data

C11H15ClN2O2	F(000) = 256
Mr = 242.70	Dx = 1.362 Mg m^−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p2yb	Cell parameters from 579 reflections
a = 9.354 (3) Å	θ = 3.7–25.0°
b = 6.7787 (12) Å	µ = 0.31 mm^−1
c = 9.566 (3) Å	T = 293 K
β = 102.720 (5)°	Prism, yellow
V = 591.7 (3) Å^3	0.22 × 0.16 × 0.12 mm
Z = 2

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	1314 independent reflections
Radiation source: fine-focus sealed tube	921 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −11→11
Tmin = 0.925, Tmax = 0.963	k = −8→8
3456 measured reflections	l = −9→11

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0449P)^2 + 0.1063P] where P = (Fo^2 + 2Fc^2)/3
1314 reflections	(Δ/σ)max < 0.001
95 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
Cl1	−0.38320 (7)	0.2500	0.33646 (8)	0.0577 (3)
O1	0.29777 (19)	0.2500	0.4861 (2)	0.0550 (6)
O2	0.1449 (2)	0.2500	0.28287 (19)	0.0575 (6)
N1	0.2041 (2)	0.2500	0.7258 (2)	0.0364 (5)
H1	0.2793	0.2500	0.6862	0.044*
N2	0.1712 (2)	0.2500	0.4146 (2)	0.0376 (5)
C1	0.0701 (2)	0.2500	0.6366 (2)	0.0292 (5)
C2	−0.0612 (3)	0.2500	0.6871 (3)	0.0349 (6)
H2	−0.0536	0.2500	0.7857	0.042*
C3	−0.1989 (2)	0.2500	0.6000 (3)	0.0352 (6)
C4	−0.2108 (3)	0.2500	0.4515 (3)	0.0361 (6)
C5	−0.0886 (3)	0.2500	0.3962 (2)	0.0347 (6)
H5	−0.0984	0.2500	0.2973	0.042*
C6	0.0503 (3)	0.2500	0.4851 (2)	0.0295 (5)
C7	−0.3320 (3)	0.2500	0.6633 (3)	0.0553 (8)
H7A	−0.3021	0.2500	0.7659	0.083*
H7B	−0.3896	0.3656	0.6323	0.083*
C8	0.2454 (3)	0.2500	0.8838 (2)	0.0370 (6)
C9	0.1935 (2)	0.0629 (3)	0.9465 (2)	0.0538 (6)
H9A	0.0885	0.0550	0.9190	0.081*
H9B	0.2235	0.0665	1.0491	0.081*
H9C	0.2356	−0.0504	0.9108	0.081*
C11	0.4129 (3)	0.2500	0.9182 (3)	0.0504 (7)
H11D	0.4474	0.3656	0.8780	0.076*
H11A	0.4491	0.2500	1.0202	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0367 (4)	0.0744 (6)	0.0534 (5)	0.000	−0.0087 (3)	0.000
O1	0.0343 (10)	0.0888 (16)	0.0446 (11)	0.000	0.0144 (9)	0.000
O2	0.0633 (13)	0.0840 (16)	0.0294 (11)	0.000	0.0195 (9)	0.000
N1	0.0283 (10)	0.0534 (14)	0.0278 (11)	0.000	0.0070 (8)	0.000
N2	0.0415 (12)	0.0399 (13)	0.0340 (12)	0.000	0.0143 (10)	0.000
C1	0.0306 (12)	0.0276 (13)	0.0287 (12)	0.000	0.0046 (10)	0.000
C2	0.0373 (13)	0.0421 (15)	0.0259 (12)	0.000	0.0086 (10)	0.000
C3	0.0313 (13)	0.0341 (14)	0.0416 (15)	0.000	0.0111 (11)	0.000
C4	0.0309 (13)	0.0336 (14)	0.0395 (14)	0.000	−0.0011 (11)	0.000
C5	0.0428 (14)	0.0322 (14)	0.0268 (13)	0.000	0.0028 (11)	0.000
C6	0.0352 (12)	0.0274 (12)	0.0280 (12)	0.000	0.0111 (10)	0.000
C7	0.0370 (14)	0.075 (2)	0.0564 (18)	0.000	0.0150 (13)	0.000
C8	0.0403 (14)	0.0410 (15)	0.0266 (13)	0.000	0.0008 (11)	0.000
C9	0.0621 (13)	0.0571 (14)	0.0400 (11)	−0.0053 (10)	0.0066 (10)	0.0089 (10)
C11	0.0428 (15)	0.062 (2)	0.0399 (15)	0.000	−0.0052 (12)	0.000

Geometric parameters (Å, º)

Cl1—C4	1.741 (2)	C4—C5	1.361 (3)
O1—N2	1.230 (3)	C5—C6	1.387 (3)
O2—N2	1.229 (3)	C5—H5	0.9300
N1—C1	1.352 (3)	C7—H7A	0.9601
N1—C8	1.476 (3)	C7—H7B	0.9600
N1—H1	0.8689	C8—C9	1.527 (2)
N2—O1	1.230 (3)	C8—C9^i	1.527 (2)
N2—C6	1.439 (3)	C8—C11	1.528 (4)
C1—C2	1.415 (3)	C9—H9A	0.9600
C1—C6	1.420 (3)	C9—H9B	0.9600
C2—C3	1.371 (3)	C9—H9C	0.9600
C2—H2	0.9300	C11—H11D	0.9598
C3—C4	1.401 (4)	C11—H11A	0.9600
C3—C7	1.500 (4)
C1—N1—C8	130.1 (2)	C6—C5—H5	119.5
C1—N1—H1	116.9	C5—C6—C1	121.3 (2)
C8—N1—H1	113.0	C5—C6—N2	116.0 (2)
O2—N2—O1	121.4 (2)	C1—C6—N2	122.6 (2)
O2—N2—O1	121.4 (2)	C3—C7—H7A	109.4
O2—N2—C6	118.7 (2)	C3—C7—H7B	109.5
O1—N2—C6	119.9 (2)	H7A—C7—H7B	109.5
O1—N2—C6	119.9 (2)	N1—C8—C9	111.60 (12)
N1—C1—C2	122.6 (2)	N1—C8—C9^i	111.60 (12)
N1—C1—C6	122.6 (2)	C9—C8—C9^i	112.3 (2)
C2—C1—C6	114.8 (2)	N1—C8—C11	104.2 (2)
C3—C2—C1	124.2 (2)	C9—C8—C11	108.38 (13)
C3—C2—H2	117.9	C9^i—C8—C11	108.38 (14)
C1—C2—H2	117.9	C8—C9—H9A	109.5
C2—C3—C4	118.1 (2)	C8—C9—H9B	109.5
C2—C3—C7	120.5 (2)	H9A—C9—H9B	109.5
C4—C3—C7	121.4 (2)	C8—C9—H9C	109.5
C5—C4—C3	120.5 (2)	H9A—C9—H9C	109.5
C5—C4—Cl1	119.7 (2)	H9B—C9—H9C	109.5
C3—C4—Cl1	119.8 (2)	C8—C11—H11D	109.5
C4—C5—C6	121.0 (2)	C8—C11—H11A	109.5
C4—C5—H5	119.5	H11D—C11—H11A	109.5
C8—N1—C1—C2	0.0	N1—C1—C6—C5	180.0
C8—N1—C1—C6	180.0	C2—C1—C6—C5	0.0
N1—C1—C2—C3	180.0	N1—C1—C6—N2	0.0
C6—C1—C2—C3	0.0	C2—C1—C6—N2	180.0
C1—C2—C3—C4	0.0	O2—N2—C6—C5	0.0
C1—C2—C3—C7	180.0	O1—N2—C6—C5	180.0
C2—C3—C4—C5	0.0	O1—N2—C6—C5	180.0
C7—C3—C4—C5	180.0	O2—N2—C6—C1	180.0
C2—C3—C4—Cl1	180.0	O1—N2—C6—C1	0.0
C7—C3—C4—Cl1	0.0	O1—N2—C6—C1	0.0
C3—C4—C5—C6	0.0	C1—N1—C8—C9	63.26 (15)
Cl1—C4—C5—C6	180.0	C1—N1—C8—C9^i	−63.26 (15)
C4—C5—C6—C1	0.0	C1—N1—C8—C11	180.0
C4—C5—C6—N2	180.0

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.87	1.96	2.628 (3)	133