5-Dimethyl-amino-N,N-dimethyl-2-nitro-benzamide.

In the title compound, C(11)H(15)N(3)O(3), one of the methyl groups attached to the benzamide unit is slightly twisted with a C-N-C-C torsion angle of 4.04 (13)°. The crystal packing is stabilized by weak intermolecular C-H⋯O hydrogen bonds together with a weak C-H⋯π inter-action.

Related literature

For nitro­aniline mustards, see: Brian et al. (1992 ▶); Rauth, (1984 ▶). For N-[(N,N-dimethyl­amino)eth­yl]carboxamide derivatives, see: Alston et al. (1983 ▶); Denny & Wilson (1986 ▶); Palmer et al. (1990 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C11H15N3O3

M = 237.26

Monoclinic,

a = 7.8581 (2) Å

b = 7.2921 (2) Å

c = 10.5183 (3) Å

β = 104.663 (1)°

V = 583.09 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.52 × 0.45 × 0.33 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.949, T max = 0.965

16075 measured reflections

3233 independent reflections

3002 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.103

S = 1.08

3233 reflections

158 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809018017/dn2453sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018017/dn2453Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H15N3O3	F(000) = 252
Mr = 237.26	Dx = 1.351 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 9204 reflections
a = 7.8581 (2) Å	θ = 2.7–40.5°
b = 7.2921 (2) Å	µ = 0.10 mm−1
c = 10.5183 (3) Å	T = 100 K
β = 104.663 (1)°	Block, yellow
V = 583.09 (3) Å3	0.52 × 0.45 × 0.33 mm
Z = 2

Bruker SMART APEXII CCD area-detector diffractometer	3233 independent reflections
Radiation source: fine-focus sealed tube	3002 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 37.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
Tmin = 0.949, Tmax = 0.965	k = −12→12
16075 measured reflections	l = −18→18

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0716P)2 + 0.0071P] where P = (Fo2 + 2Fc2)/3
3233 reflections	(Δ/σ)max < 0.001
158 parameters	Δρmax = 0.64 e Å−3
1 restraint	Δρmin = −0.19 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
O1	0.42663 (10)	1.04274 (10)	0.31204 (7)	0.01969 (13)
O2	0.81992 (10)	0.62755 (17)	0.20077 (10)	0.0334 (2)
O3	0.71314 (10)	0.76718 (13)	0.34531 (8)	0.02322 (15)
N1	0.32548 (10)	0.78907 (13)	0.39646 (8)	0.01811 (14)
N2	0.03825 (10)	0.70383 (12)	−0.13123 (8)	0.01594 (13)
N3	0.69532 (10)	0.69824 (13)	0.23538 (9)	0.01899 (15)
C1	0.21826 (10)	0.78067 (12)	0.08485 (8)	0.01443 (13)
H1A	0.1210	0.8309	0.1072	0.017*
C2	0.19805 (10)	0.70835 (12)	−0.04364 (9)	0.01396 (13)
C3	0.35014 (11)	0.63797 (13)	−0.07614 (9)	0.01687 (15)
H3A	0.3427	0.5950	−0.1606	0.020*
C4	0.50889 (12)	0.63311 (14)	0.01717 (10)	0.01789 (16)
H4A	0.6070	0.5837	−0.0045	0.021*
C5	0.52463 (11)	0.70133 (13)	0.14373 (9)	0.01538 (14)
C6	0.37880 (10)	0.77846 (12)	0.17780 (8)	0.01392 (13)
C7	0.38381 (11)	0.87931 (13)	0.30423 (8)	0.01530 (14)
C8	0.30516 (14)	0.88622 (18)	0.51258 (10)	0.02438 (19)
H8A	0.3409	1.0116	0.5088	0.037*
H8B	0.3770	0.8290	0.5899	0.037*
H8C	0.1842	0.8822	0.5156	0.037*
C9	0.26858 (13)	0.59813 (16)	0.38621 (11)	0.02241 (18)
H9A	0.3149	0.5368	0.3215	0.034*
H9B	0.1424	0.5930	0.3606	0.034*
H9C	0.3109	0.5389	0.4698	0.034*
C10	−0.11334 (12)	0.79019 (15)	−0.10016 (10)	0.02084 (17)
H10A	−0.1220	0.7503	−0.0151	0.031*
H10B	−0.2183	0.7562	−0.1650	0.031*
H10C	−0.0997	0.9210	−0.0999	0.031*
C11	0.02302 (13)	0.65472 (17)	−0.26808 (10)	0.02261 (18)
H11A	0.0664	0.5324	−0.2724	0.034*
H11B	0.0908	0.7388	−0.3056	0.034*
H11C	−0.0982	0.6607	−0.3163	0.034*

	U11	U22	U33	U12	U13	U23
O1	0.0221 (3)	0.0166 (3)	0.0198 (3)	−0.0026 (2)	0.0044 (2)	−0.0016 (2)
O2	0.0152 (3)	0.0482 (6)	0.0356 (4)	0.0109 (3)	0.0039 (3)	−0.0048 (4)
O3	0.0180 (3)	0.0286 (4)	0.0212 (3)	−0.0001 (3)	0.0016 (2)	0.0009 (3)
N1	0.0175 (3)	0.0211 (4)	0.0163 (3)	−0.0025 (3)	0.0053 (2)	0.0010 (3)
N2	0.0142 (3)	0.0169 (3)	0.0162 (3)	0.0002 (2)	0.0029 (2)	−0.0020 (3)
N3	0.0132 (3)	0.0199 (3)	0.0232 (3)	0.0010 (3)	0.0033 (2)	0.0028 (3)
C1	0.0119 (3)	0.0156 (3)	0.0163 (3)	0.0001 (2)	0.0045 (2)	−0.0015 (3)
C2	0.0134 (3)	0.0125 (3)	0.0162 (3)	−0.0006 (2)	0.0042 (2)	−0.0005 (3)
C3	0.0154 (3)	0.0165 (3)	0.0198 (4)	0.0002 (3)	0.0065 (3)	−0.0033 (3)
C4	0.0142 (3)	0.0175 (4)	0.0230 (4)	0.0013 (3)	0.0065 (3)	−0.0022 (3)
C5	0.0117 (3)	0.0151 (3)	0.0191 (3)	0.0008 (3)	0.0036 (2)	0.0010 (3)
C6	0.0128 (3)	0.0134 (3)	0.0159 (3)	−0.0007 (2)	0.0043 (2)	0.0011 (3)
C7	0.0131 (3)	0.0175 (3)	0.0150 (3)	−0.0004 (3)	0.0029 (2)	0.0003 (3)
C8	0.0253 (4)	0.0322 (5)	0.0174 (4)	0.0020 (4)	0.0086 (3)	0.0002 (4)
C9	0.0205 (4)	0.0228 (4)	0.0232 (4)	−0.0045 (3)	0.0041 (3)	0.0059 (3)
C10	0.0145 (3)	0.0253 (4)	0.0214 (4)	0.0033 (3)	0.0020 (3)	−0.0045 (4)
C11	0.0208 (4)	0.0303 (5)	0.0164 (3)	−0.0019 (3)	0.0040 (3)	−0.0045 (3)

O1—C7	1.2354 (12)	C4—C5	1.3969 (13)
O2—N3	1.2400 (12)	C4—H4A	0.9300
O3—N3	1.2358 (12)	C5—C6	1.4021 (11)
N1—C7	1.3450 (12)	C6—C7	1.5115 (13)
N1—C8	1.4553 (13)	C8—H8A	0.9600
N1—C9	1.4580 (14)	C8—H8B	0.9600
N2—C2	1.3569 (11)	C8—H8C	0.9600
N2—C10	1.4558 (12)	C9—H9A	0.9600
N2—C11	1.4585 (12)	C9—H9B	0.9600
N3—C5	1.4403 (12)	C9—H9C	0.9600
C1—C6	1.3868 (11)	C10—H10A	0.9600
C1—C2	1.4216 (12)	C10—H10B	0.9600
C1—H1A	0.9300	C10—H10C	0.9600
C2—C3	1.4197 (11)	C11—H11A	0.9600
C3—C4	1.3787 (12)	C11—H11B	0.9600
C3—H3A	0.9300	C11—H11C	0.9600
C7—N1—C8	119.80 (9)	O1—C7—N1	124.11 (9)
C7—N1—C9	124.61 (8)	O1—C7—C6	118.29 (8)
C8—N1—C9	115.48 (8)	N1—C7—C6	117.31 (8)
C2—N2—C10	120.41 (7)	N1—C8—H8A	109.5
C2—N2—C11	120.45 (7)	N1—C8—H8B	109.5
C10—N2—C11	117.41 (8)	H8A—C8—H8B	109.5
O3—N3—O2	122.21 (9)	N1—C8—H8C	109.5
O3—N3—C5	119.06 (8)	H8A—C8—H8C	109.5
O2—N3—C5	118.74 (9)	H8B—C8—H8C	109.5
C6—C1—C2	121.92 (7)	N1—C9—H9A	109.5
C6—C1—H1A	119.0	N1—C9—H9B	109.5
C2—C1—H1A	119.0	H9A—C9—H9B	109.5
N2—C2—C3	121.23 (8)	N1—C9—H9C	109.5
N2—C2—C1	121.07 (7)	H9A—C9—H9C	109.5
C3—C2—C1	117.69 (7)	H9B—C9—H9C	109.5
C4—C3—C2	120.20 (8)	N2—C10—H10A	109.5
C4—C3—H3A	119.9	N2—C10—H10B	109.5
C2—C3—H3A	119.9	H10A—C10—H10B	109.5
C3—C4—C5	121.00 (8)	N2—C10—H10C	109.5
C3—C4—H4A	119.5	H10A—C10—H10C	109.5
C5—C4—H4A	119.5	H10B—C10—H10C	109.5
C4—C5—C6	120.36 (8)	N2—C11—H11A	109.5
C4—C5—N3	118.37 (7)	N2—C11—H11B	109.5
C6—C5—N3	121.20 (8)	H11A—C11—H11B	109.5
C1—C6—C5	118.75 (8)	N2—C11—H11C	109.5
C1—C6—C7	115.54 (7)	H11A—C11—H11C	109.5
C5—C6—C7	125.39 (7)	H11B—C11—H11C	109.5
C10—N2—C2—C3	−174.89 (9)	C2—C1—C6—C5	−0.44 (13)
C11—N2—C2—C3	−10.25 (14)	C2—C1—C6—C7	173.36 (8)
C10—N2—C2—C1	6.32 (14)	C4—C5—C6—C1	1.86 (13)
C11—N2—C2—C1	170.96 (9)	N3—C5—C6—C1	178.85 (8)
C6—C1—C2—N2	176.85 (9)	C4—C5—C6—C7	−171.28 (9)
C6—C1—C2—C3	−1.98 (13)	N3—C5—C6—C7	5.71 (14)
N2—C2—C3—C4	−175.78 (9)	C8—N1—C7—O1	1.74 (14)
C1—C2—C3—C4	3.05 (13)	C9—N1—C7—O1	177.67 (9)
C2—C3—C4—C5	−1.73 (15)	C8—N1—C7—C6	−171.90 (8)
C3—C4—C5—C6	−0.79 (15)	C9—N1—C7—C6	4.04 (13)
C3—C4—C5—N3	−177.86 (9)	C1—C6—C7—O1	−91.10 (10)
O3—N3—C5—C4	176.11 (9)	C5—C6—C7—O1	82.24 (12)
O2—N3—C5—C4	−3.35 (14)	C1—C6—C7—N1	82.91 (10)
O3—N3—C5—C6	−0.94 (14)	C5—C6—C7—N1	−103.75 (10)
O2—N3—C5—C6	179.61 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O3i	0.96	2.52	3.1751 (16)	126
C10—H10A···O2ii	0.96	2.59	3.5413 (14)	173
C10—H10B···O1iii	0.96	2.49	3.3920 (13)	156
C4—H4A···Cg1iv	0.93	2.81	3.3991 (11)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O3i	0.96	2.52	3.1751 (16)	126
C10—H10A⋯O2ii	0.96	2.59	3.5413 (14)	173
C10—H10B⋯O1iii	0.96	2.49	3.3920 (13)	156
C4—H4A⋯Cg1iv	0.93	2.81	3.3991 (11)	122

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C1–C6 ring.