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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804030570/gh6007sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804030570/gh6007Isup2.hkl
Contains datablock I

CCDC reference: 259860

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

Computing details top

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 top
Crystal data top
C11H15ClN2O2F(000) = 256
Mr = 242.70Dx = 1.362 Mg m3
Monoclinic, P21/mMo Kα radiation, λ = 0.71073 Å
Hall symbol: -p2ybCell parameters from 579 reflections
a = 9.354 (3) Åθ = 3.7–25.0°
b = 6.7787 (12) ŵ = 0.31 mm1
c = 9.566 (3) ÅT = 293 K
β = 102.720 (5)°Prism, yellow
V = 591.7 (3) Å30.22 × 0.16 × 0.12 mm
Z = 2
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
1314 independent reflections
Radiation source: fine-focus sealed tube921 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
φ and ω scansθmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 1111
Tmin = 0.925, Tmax = 0.963k = 88
3456 measured reflectionsl = 911
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0449P)2 + 0.1063P]
where P = (Fo2 + 2Fc2)/3
1314 reflections(Δ/σ)max < 0.001
95 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.19 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cl10.38320 (7)0.25000.33646 (8)0.0577 (3)
O10.29777 (19)0.25000.4861 (2)0.0550 (6)
O20.1449 (2)0.25000.28287 (19)0.0575 (6)
N10.2041 (2)0.25000.7258 (2)0.0364 (5)
H10.27930.25000.68620.044*
N20.1712 (2)0.25000.4146 (2)0.0376 (5)
C10.0701 (2)0.25000.6366 (2)0.0292 (5)
C20.0612 (3)0.25000.6871 (3)0.0349 (6)
H20.05360.25000.78570.042*
C30.1989 (2)0.25000.6000 (3)0.0352 (6)
C40.2108 (3)0.25000.4515 (3)0.0361 (6)
C50.0886 (3)0.25000.3962 (2)0.0347 (6)
H50.09840.25000.29730.042*
C60.0503 (3)0.25000.4851 (2)0.0295 (5)
C70.3320 (3)0.25000.6633 (3)0.0553 (8)
H7A0.30210.25000.76590.083*
H7B0.38960.36560.63230.083*
C80.2454 (3)0.25000.8838 (2)0.0370 (6)
C90.1935 (2)0.0629 (3)0.9465 (2)0.0538 (6)
H9A0.08850.05500.91900.081*
H9B0.22350.06651.04910.081*
H9C0.23560.05040.91080.081*
C110.4129 (3)0.25000.9182 (3)0.0504 (7)
H11D0.44740.36560.87800.076*
H11A0.44910.25001.02020.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0367 (4)0.0744 (6)0.0534 (5)0.0000.0087 (3)0.000
O10.0343 (10)0.0888 (16)0.0446 (11)0.0000.0144 (9)0.000
O20.0633 (13)0.0840 (16)0.0294 (11)0.0000.0195 (9)0.000
N10.0283 (10)0.0534 (14)0.0278 (11)0.0000.0070 (8)0.000
N20.0415 (12)0.0399 (13)0.0340 (12)0.0000.0143 (10)0.000
C10.0306 (12)0.0276 (13)0.0287 (12)0.0000.0046 (10)0.000
C20.0373 (13)0.0421 (15)0.0259 (12)0.0000.0086 (10)0.000
C30.0313 (13)0.0341 (14)0.0416 (15)0.0000.0111 (11)0.000
C40.0309 (13)0.0336 (14)0.0395 (14)0.0000.0011 (11)0.000
C50.0428 (14)0.0322 (14)0.0268 (13)0.0000.0028 (11)0.000
C60.0352 (12)0.0274 (12)0.0280 (12)0.0000.0111 (10)0.000
C70.0370 (14)0.075 (2)0.0564 (18)0.0000.0150 (13)0.000
C80.0403 (14)0.0410 (15)0.0266 (13)0.0000.0008 (11)0.000
C90.0621 (13)0.0571 (14)0.0400 (11)0.0053 (10)0.0066 (10)0.0089 (10)
C110.0428 (15)0.062 (2)0.0399 (15)0.0000.0052 (12)0.000
Geometric parameters (Å, º) top
Cl1—C41.741 (2)C4—C51.361 (3)
O1—N21.230 (3)C5—C61.387 (3)
O2—N21.229 (3)C5—H50.9300
N1—C11.352 (3)C7—H7A0.9601
N1—C81.476 (3)C7—H7B0.9600
N1—H10.8689C8—C91.527 (2)
N2—O11.230 (3)C8—C9i1.527 (2)
N2—C61.439 (3)C8—C111.528 (4)
C1—C21.415 (3)C9—H9A0.9600
C1—C61.420 (3)C9—H9B0.9600
C2—C31.371 (3)C9—H9C0.9600
C2—H20.9300C11—H11D0.9598
C3—C41.401 (4)C11—H11A0.9600
C3—C71.500 (4)
C1—N1—C8130.1 (2)C6—C5—H5119.5
C1—N1—H1116.9C5—C6—C1121.3 (2)
C8—N1—H1113.0C5—C6—N2116.0 (2)
O2—N2—O1121.4 (2)C1—C6—N2122.6 (2)
O2—N2—O1121.4 (2)C3—C7—H7A109.4
O2—N2—C6118.7 (2)C3—C7—H7B109.5
O1—N2—C6119.9 (2)H7A—C7—H7B109.5
O1—N2—C6119.9 (2)N1—C8—C9111.60 (12)
N1—C1—C2122.6 (2)N1—C8—C9i111.60 (12)
N1—C1—C6122.6 (2)C9—C8—C9i112.3 (2)
C2—C1—C6114.8 (2)N1—C8—C11104.2 (2)
C3—C2—C1124.2 (2)C9—C8—C11108.38 (13)
C3—C2—H2117.9C9i—C8—C11108.38 (14)
C1—C2—H2117.9C8—C9—H9A109.5
C2—C3—C4118.1 (2)C8—C9—H9B109.5
C2—C3—C7120.5 (2)H9A—C9—H9B109.5
C4—C3—C7121.4 (2)C8—C9—H9C109.5
C5—C4—C3120.5 (2)H9A—C9—H9C109.5
C5—C4—Cl1119.7 (2)H9B—C9—H9C109.5
C3—C4—Cl1119.8 (2)C8—C11—H11D109.5
C4—C5—C6121.0 (2)C8—C11—H11A109.5
C4—C5—H5119.5H11D—C11—H11A109.5
C8—N1—C1—C20.0N1—C1—C6—C5180.0
C8—N1—C1—C6180.0C2—C1—C6—C50.0
N1—C1—C2—C3180.0N1—C1—C6—N20.0
C6—C1—C2—C30.0C2—C1—C6—N2180.0
C1—C2—C3—C40.0O2—N2—C6—C50.0
C1—C2—C3—C7180.0O1—N2—C6—C5180.0
C2—C3—C4—C50.0O1—N2—C6—C5180.0
C7—C3—C4—C5180.0O2—N2—C6—C1180.0
C2—C3—C4—Cl1180.0O1—N2—C6—C10.0
C7—C3—C4—Cl10.0O1—N2—C6—C10.0
C3—C4—C5—C60.0C1—N1—C8—C963.26 (15)
Cl1—C4—C5—C6180.0C1—N1—C8—C9i63.26 (15)
C4—C5—C6—C10.0C1—N1—C8—C11180.0
C4—C5—C6—N2180.0
Symmetry code: (i) x, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.871.962.628 (3)133
 

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