N-(2,4-Dinitro-phen-yl)-1,3-dimeth-oxy-isoindolin-2-amine.

In the title compound, C(16)H(16)N(4)O(6), the planes of the isoindole and dinitro-benzene groups make a dihedral angle between of 84.15 (8)°. The N atom of the isoindole group is displaced by 0.2937 (3) Å from the plane through the remaining atoms. An intra-molecular N-H⋯O inter-action occurs. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds occur.

Related literature

For general background to isoindoles and their derivatives, see: Mancilla et al. (2007 ▶); Toru et al. (1986 ▶). For the synthetic method and related structures, see: Maliha et al. (2008 ▶, 2009 ▶).

Experimental

Crystal data

C16H16N4O6

M = 360.33

Triclinic,

a = 7.727 (4) Å

b = 10.244 (5) Å

c = 11.326 (6) Å

α = 86.076 (9)°

β = 77.705 (8)°

γ = 70.794 (8)°

V = 827.2 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.16 × 0.14 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.982, T max = 0.989

4365 measured reflections

3181 independent reflections

2045 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.225

S = 1.02

3181 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811026316/ez2248sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026316/ez2248Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811026316/ez2248Isup3.cml

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

C16H16N4O6	Z = 2
Mr = 360.33	F(000) = 376
Triclinic, P1	Dx = 1.447 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.727 (4) Å	Cell parameters from 1638 reflections
b = 10.244 (5) Å	θ = 2.8–27.5°
c = 11.326 (6) Å	µ = 0.11 mm−1
α = 86.076 (9)°	T = 296 K
β = 77.705 (8)°	Block, colorless
γ = 70.794 (8)°	0.16 × 0.14 × 0.10 mm
V = 827.2 (7) Å3

Bruker SMART APEXII CCD diffractometer	3181 independent reflections
Radiation source: fine-focus sealed tube	2045 reflections with I > 2σ(I)
graphite	Rint = 0.062
phi and ω scans	θmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
Tmin = 0.982, Tmax = 0.989	k = −11→12
4365 measured reflections	l = −13→13

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.225	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.1489P)2] where P = (Fo2 + 2Fc2)/3
3181 reflections	(Δ/σ)max < 0.001
237 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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
C1	0.1312 (5)	0.1163 (3)	0.6041 (3)	0.0665 (9)
H1	0.1032	0.0400	0.6417	0.080*
C2	0.1069 (5)	0.1515 (4)	0.4885 (3)	0.0741 (10)
H2	0.0623	0.0983	0.4471	0.089*
C3	0.1476 (5)	0.2646 (4)	0.4328 (3)	0.0684 (9)
H3	0.1297	0.2869	0.3543	0.082*
C4	0.2142 (4)	0.3446 (3)	0.4915 (3)	0.0588 (8)
H4	0.2414	0.4212	0.4539	0.071*
C5	0.2401 (4)	0.3088 (3)	0.6080 (2)	0.0451 (6)
C6	0.1985 (4)	0.1974 (3)	0.6640 (2)	0.0487 (7)
C7	0.2308 (4)	0.1839 (3)	0.7897 (2)	0.0501 (7)
H7	0.1096	0.2205	0.8450	0.060*
C8	0.3055 (4)	0.3813 (3)	0.6914 (2)	0.0450 (6)
H8	0.2013	0.4633	0.7241	0.054*
C9	0.4404 (3)	0.3127 (2)	0.9664 (2)	0.0404 (6)
C10	0.4134 (3)	0.3760 (2)	1.0796 (2)	0.0405 (6)
C11	0.5561 (4)	0.3448 (2)	1.1440 (2)	0.0436 (6)
H11	0.5367	0.3873	1.2179	0.052*
C12	0.7242 (4)	0.2512 (3)	1.0975 (2)	0.0478 (7)
C13	0.7560 (4)	0.1846 (3)	0.9883 (2)	0.0516 (7)
H13	0.8714	0.1193	0.9589	0.062*
C14	0.6169 (4)	0.2160 (3)	0.9250 (2)	0.0496 (7)
H14	0.6395	0.1717	0.8516	0.060*
C15	0.4939 (5)	−0.0207 (3)	0.7495 (4)	0.0802 (10)
H15A	0.4677	−0.0681	0.6887	0.120*
H15B	0.5744	−0.0866	0.7950	0.120*
H15C	0.5546	0.0439	0.7116	0.120*
C16	0.6218 (5)	0.3179 (3)	0.5833 (3)	0.0656 (8)
H16A	0.6744	0.2530	0.6417	0.098*
H16B	0.7128	0.3590	0.5413	0.098*
H16C	0.5869	0.2708	0.5265	0.098*
N1	0.3375 (3)	0.2795 (2)	0.78934 (18)	0.0438 (5)
N2	0.3060 (3)	0.3424 (2)	0.90125 (19)	0.0499 (6)
H2A	0.1982	0.4013	0.9289	0.060*
N3	0.2382 (3)	0.4743 (2)	1.13435 (19)	0.0478 (6)
N4	0.8726 (4)	0.2154 (3)	1.1652 (3)	0.0671 (8)
O1	0.1085 (3)	0.5064 (3)	1.0803 (2)	0.0811 (8)
O2	0.2215 (3)	0.5263 (2)	1.23014 (19)	0.0758 (7)
O3	1.0248 (4)	0.1387 (4)	1.1204 (3)	0.1139 (12)
O4	0.8371 (4)	0.2619 (3)	1.2668 (3)	0.1046 (11)
O5	0.3227 (3)	0.0518 (2)	0.8286 (2)	0.0697 (6)
O6	0.4614 (3)	0.42259 (18)	0.64289 (17)	0.0553 (6)

	U11	U22	U33	U12	U13	U23
C1	0.078 (2)	0.0666 (19)	0.071 (2)	−0.0393 (17)	−0.0207 (17)	−0.0068 (15)
C2	0.078 (2)	0.087 (2)	0.073 (2)	−0.0333 (19)	−0.0310 (18)	−0.0206 (18)
C3	0.077 (2)	0.082 (2)	0.0539 (18)	−0.0243 (18)	−0.0284 (16)	−0.0103 (16)
C4	0.074 (2)	0.0550 (17)	0.0505 (17)	−0.0184 (15)	−0.0220 (14)	−0.0007 (13)
C5	0.0475 (15)	0.0434 (13)	0.0443 (14)	−0.0093 (11)	−0.0157 (11)	−0.0063 (11)
C6	0.0502 (15)	0.0503 (15)	0.0488 (15)	−0.0158 (12)	−0.0156 (12)	−0.0062 (12)
C7	0.0563 (16)	0.0491 (15)	0.0472 (15)	−0.0189 (12)	−0.0116 (12)	−0.0027 (12)
C8	0.0533 (15)	0.0390 (13)	0.0429 (14)	−0.0110 (11)	−0.0147 (11)	−0.0043 (10)
C9	0.0470 (14)	0.0391 (13)	0.0373 (13)	−0.0139 (11)	−0.0139 (11)	0.0029 (10)
C10	0.0463 (14)	0.0361 (12)	0.0380 (13)	−0.0112 (10)	−0.0100 (11)	0.0007 (10)
C11	0.0552 (16)	0.0383 (13)	0.0406 (14)	−0.0156 (11)	−0.0160 (12)	0.0006 (10)
C12	0.0504 (16)	0.0435 (14)	0.0530 (16)	−0.0139 (12)	−0.0208 (12)	0.0029 (11)
C13	0.0493 (16)	0.0480 (15)	0.0534 (16)	−0.0084 (12)	−0.0127 (13)	−0.0026 (12)
C14	0.0523 (16)	0.0522 (15)	0.0425 (14)	−0.0110 (13)	−0.0131 (12)	−0.0060 (12)
C15	0.087 (3)	0.0460 (17)	0.101 (3)	−0.0132 (17)	−0.020 (2)	0.0006 (17)
C16	0.067 (2)	0.0663 (19)	0.0624 (19)	−0.0253 (16)	−0.0027 (15)	−0.0038 (15)
N1	0.0538 (13)	0.0420 (11)	0.0369 (11)	−0.0127 (10)	−0.0142 (9)	−0.0062 (9)
N2	0.0485 (13)	0.0547 (13)	0.0413 (12)	−0.0047 (10)	−0.0136 (10)	−0.0118 (10)
N3	0.0526 (13)	0.0487 (12)	0.0406 (12)	−0.0100 (10)	−0.0152 (10)	−0.0038 (9)
N4	0.0626 (17)	0.0641 (16)	0.0746 (18)	−0.0036 (13)	−0.0367 (14)	−0.0125 (14)
O1	0.0548 (13)	0.1044 (18)	0.0684 (15)	0.0123 (12)	−0.0283 (11)	−0.0361 (13)
O2	0.0744 (15)	0.0890 (16)	0.0526 (13)	0.0012 (12)	−0.0230 (11)	−0.0312 (11)
O3	0.0634 (16)	0.139 (3)	0.122 (2)	0.0166 (17)	−0.0444 (16)	−0.052 (2)
O4	0.0970 (19)	0.111 (2)	0.094 (2)	0.0161 (16)	−0.0634 (16)	−0.0374 (17)
O5	0.0905 (16)	0.0517 (12)	0.0685 (14)	−0.0258 (11)	−0.0194 (12)	0.0151 (10)
O6	0.0670 (13)	0.0474 (11)	0.0574 (12)	−0.0267 (10)	−0.0108 (10)	−0.0039 (9)

C1—C2	1.369 (5)	C10—N3	1.436 (3)
C1—C6	1.390 (4)	C11—C12	1.357 (4)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.376 (5)	C12—C13	1.390 (4)
C2—H2	0.9300	C12—N4	1.448 (4)
C3—C4	1.370 (4)	C13—C14	1.358 (4)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.384 (4)	C14—H14	0.9300
C4—H4	0.9300	C15—O5	1.430 (4)
C5—C6	1.365 (4)	C15—H15A	0.9600
C5—C8	1.499 (3)	C15—H15B	0.9600
C6—C7	1.486 (4)	C15—H15C	0.9600
C7—O5	1.396 (4)	C16—O6	1.418 (4)
C7—N1	1.473 (3)	C16—H16A	0.9600
C7—H7	0.9800	C16—H16B	0.9600
C8—O6	1.397 (3)	C16—H16C	0.9600
C8—N1	1.472 (3)	N1—N2	1.399 (3)
C8—H8	0.9800	N2—H2A	0.8600
C9—N2	1.343 (3)	N3—O2	1.205 (3)
C9—C14	1.401 (4)	N3—O1	1.227 (3)
C9—C10	1.421 (3)	N4—O3	1.204 (3)
C10—C11	1.388 (4)	N4—O4	1.217 (3)
C2—C1—C6	118.4 (3)	C12—C11—H11	120.5
C2—C1—H1	120.8	C10—C11—H11	120.5
C6—C1—H1	120.8	C11—C12—C13	121.7 (2)
C1—C2—C3	121.0 (3)	C11—C12—N4	119.4 (3)
C1—C2—H2	119.5	C13—C12—N4	118.8 (2)
C3—C2—H2	119.5	C14—C13—C12	119.3 (3)
C4—C3—C2	120.8 (3)	C14—C13—H13	120.4
C4—C3—H3	119.6	C12—C13—H13	120.4
C2—C3—H3	119.6	C13—C14—C9	122.3 (2)
C3—C4—C5	118.4 (3)	C13—C14—H14	118.8
C3—C4—H4	120.8	C9—C14—H14	118.8
C5—C4—H4	120.8	O5—C15—H15A	109.5
C6—C5—C4	121.1 (3)	O5—C15—H15B	109.5
C6—C5—C8	110.5 (2)	H15A—C15—H15B	109.5
C4—C5—C8	128.4 (3)	O5—C15—H15C	109.5
C5—C6—C1	120.4 (3)	H15A—C15—H15C	109.5
C5—C6—C7	110.8 (2)	H15B—C15—H15C	109.5
C1—C6—C7	128.8 (3)	O6—C16—H16A	109.5
O5—C7—N1	112.1 (2)	O6—C16—H16B	109.5
O5—C7—C6	117.2 (2)	H16A—C16—H16B	109.5
N1—C7—C6	101.9 (2)	O6—C16—H16C	109.5
O5—C7—H7	108.4	H16A—C16—H16C	109.5
N1—C7—H7	108.4	H16B—C16—H16C	109.5
C6—C7—H7	108.4	N2—N1—C8	112.18 (19)
O6—C8—N1	113.0 (2)	N2—N1—C7	113.7 (2)
O6—C8—C5	117.0 (2)	C8—N1—C7	110.43 (19)
N1—C8—C5	101.6 (2)	C9—N2—N1	121.4 (2)
O6—C8—H8	108.3	C9—N2—H2A	119.3
N1—C8—H8	108.3	N1—N2—H2A	119.3
C5—C8—H8	108.3	O2—N3—O1	121.1 (2)
N2—C9—C14	121.0 (2)	O2—N3—C10	120.2 (2)
N2—C9—C10	122.7 (2)	O1—N3—C10	118.7 (2)
C14—C9—C10	116.3 (2)	O3—N4—O4	122.5 (3)
C11—C10—C9	121.4 (2)	O3—N4—C12	119.1 (3)
C11—C10—N3	116.3 (2)	O4—N4—C12	118.4 (3)
C9—C10—N3	122.3 (2)	C7—O5—C15	114.8 (2)
C12—C11—C10	118.9 (2)	C8—O6—C16	115.8 (2)
C6—C1—C2—C3	−0.2 (5)	N4—C12—C13—C14	179.1 (3)
C1—C2—C3—C4	0.2 (5)	C12—C13—C14—C9	−0.6 (4)
C2—C3—C4—C5	0.2 (5)	N2—C9—C14—C13	179.4 (2)
C3—C4—C5—C6	−0.7 (4)	C10—C9—C14—C13	−0.6 (4)
C3—C4—C5—C8	−178.1 (3)	O6—C8—N1—N2	84.6 (3)
C4—C5—C6—C1	0.8 (4)	C5—C8—N1—N2	−149.3 (2)
C8—C5—C6—C1	178.6 (3)	O6—C8—N1—C7	−147.5 (2)
C4—C5—C6—C7	−177.7 (2)	C5—C8—N1—C7	−21.3 (3)
C8—C5—C6—C7	0.2 (3)	O5—C7—N1—N2	−85.2 (3)
C2—C1—C6—C5	−0.3 (5)	C6—C7—N1—N2	148.6 (2)
C2—C1—C6—C7	177.8 (3)	O5—C7—N1—C8	147.7 (2)
C5—C6—C7—O5	−135.8 (3)	C6—C7—N1—C8	21.5 (3)
C1—C6—C7—O5	46.0 (4)	C14—C9—N2—N1	−0.8 (4)
C5—C6—C7—N1	−13.0 (3)	C10—C9—N2—N1	179.2 (2)
C1—C6—C7—N1	168.7 (3)	C8—N1—N2—C9	−122.1 (3)
C6—C5—C8—O6	136.2 (2)	C7—N1—N2—C9	111.7 (3)
C4—C5—C8—O6	−46.1 (4)	C11—C10—N3—O2	1.0 (4)
C6—C5—C8—N1	12.7 (3)	C9—C10—N3—O2	−179.5 (3)
C4—C5—C8—N1	−169.6 (3)	C11—C10—N3—O1	179.2 (2)
N2—C9—C10—C11	−179.0 (2)	C9—C10—N3—O1	−1.4 (4)
C14—C9—C10—C11	1.0 (4)	C11—C12—N4—O3	−175.6 (3)
N2—C9—C10—N3	1.6 (4)	C13—C12—N4—O3	6.7 (5)
C14—C9—C10—N3	−178.4 (2)	C11—C12—N4—O4	6.0 (5)
C9—C10—C11—C12	−0.3 (4)	C13—C12—N4—O4	−171.6 (3)
N3—C10—C11—C12	179.2 (2)	N1—C7—O5—C15	−66.5 (3)
C10—C11—C12—C13	−1.0 (4)	C6—C7—O5—C15	50.8 (3)
C10—C11—C12—N4	−178.6 (2)	N1—C8—O6—C16	64.6 (3)
C11—C12—C13—C14	1.5 (4)	C5—C8—O6—C16	−52.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.96	2.593 (3)	130
N2—H2A···O1i	0.86	2.27	3.032 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	1.96	2.593 (3)	130
N2—H2A⋯O1i	0.86	2.27	3.032 (3)	148

Symmetry code: (i) .