Dipentyl 2,6-di-amino-benzo[1,2-b:4,5-b']di-furan-3,7-di-carboxyl-ate.

The title compound, C22H28N2O6, crystallizes with one half-mol-ecule in the independent unit, the mol-ecule being located on an inversion centre. The penthyl groups are in the all-trans conformation and an almost planar conformation of the whole mol-ecule is observed [maximum deviation from the least-squares plane through all non-H atoms is 0.0229 (17) Å for an N atom]. The amino groups are involved in intra- and inter-molecular hydrogen bonds. Intra-molecular hydrogen bonding involving the amino group and ester carbonyl helps to lock the syn conformation of the ester with respect to the amino group. In the crystal, N-H⋯O hydrogen bonding involving the amino group and the furan and ester carbonyl O atoms self-assembles the mol-ecules into a two-dimensional hydrogen-bonded network parallel to (010) that displays inter-digital packing sustained by alk-yl-alkyl inter-actions.

Related literature

For the synthesis and properties of amino­benzodi­furane derivatives, see: Caruso et al. (2009 ▶). For O- and N-rich aromatic heterocycles, see: Roviello et al. (2007 ▶, 2012 ▶). For mol­ecules with optical and opto-electronical properties, see: Carella et al. (2012 ▶); Centore et al. (2007 ▶); Roviello et al. (2009 ▶); Ricciotti et al. (2013 ▶); Vitaliano et al. (2009 ▶). For hydrogen bonding in heterocycles, see: Centore et al. (2013a ▶,b ▶).

Experimental

Crystal data

C22H28N2O6

M = 416.46

Monoclinic,

a = 8.267 (1) Å

b = 7.994 (1) Å

c = 17.582 (3) Å

β = 98.98 (2)°

V = 1147.7 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.50 × 0.04 × 0.01 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.957, T max = 0.999

11093 measured reflections

2626 independent reflections

1258 reflections with I > 2σ(I)

R int = 0.096

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.134

S = 0.93

2626 reflections

142 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000 ▶); data reduction: EVALCCD (Duisenberg et al., 2003 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681302480X/ds2234sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302480X/ds2234Isup2.hkl

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

C22H28N2O6	F(000) = 444
Mr = 416.46	Dx = 1.205 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 75 reflections
a = 8.267 (1) Å	θ = 3.1–16.9°
b = 7.994 (1) Å	µ = 0.09 mm−1
c = 17.582 (3) Å	T = 173 K
β = 98.98 (2)°	Block, grey
V = 1147.7 (3) Å3	0.50 × 0.04 × 0.01 mm
Z = 2

Bruker–Nonius KappaCCD diffractometer	2626 independent reflections
Radiation source: normal-focus sealed tube	1258 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.096
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 3.2°
CCD rotation images, thick slices scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −10→9
Tmin = 0.957, Tmax = 0.999	l = −22→22
11093 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ2(Fo2) + (0.061P)2] where P = (Fo2 + 2Fc2)/3
2626 reflections	(Δ/σ)max < 0.001
142 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.20 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	0.5923 (2)	0.1341 (3)	0.04464 (11)	0.0257 (5)
H1	0.6556	0.2314	0.0731	0.026*
C2	0.5354 (2)	−0.0094 (3)	0.07682 (11)	0.0246 (5)
C3	0.4461 (2)	−0.1426 (3)	0.03695 (11)	0.0255 (5)
C4	0.4171 (2)	−0.2648 (3)	0.09645 (11)	0.0254 (5)
C5	0.4884 (3)	−0.1957 (3)	0.16650 (12)	0.0282 (5)
C6	0.3356 (2)	−0.4269 (3)	0.09113 (12)	0.0288 (6)
C7	0.1878 (3)	−0.6355 (3)	0.00858 (11)	0.0326 (6)
H7A	0.0935	−0.6356	0.0370	0.033*
H7B	0.2644	−0.7250	0.0301	0.033*
C8	0.1290 (3)	−0.6679 (3)	−0.07634 (12)	0.0340 (6)
H8A	0.2242	−0.6700	−0.1043	0.034*
H8B	0.0556	−0.5760	−0.0979	0.034*
C9	0.0363 (3)	−0.8366 (3)	−0.08811 (12)	0.0382 (6)
H9A	0.1101	−0.9271	−0.0654	0.038*
H9B	−0.0583	−0.8331	−0.0598	0.038*
C10	−0.0261 (3)	−0.8793 (3)	−0.17302 (13)	0.0472 (7)
H10A	0.0678	−0.8822	−0.2017	0.047*
H10B	−0.1019	−0.7904	−0.1958	0.047*
C11	−0.1155 (4)	−1.0494 (3)	−0.18205 (16)	0.0632 (8)
H11A	−0.1539	−1.0711	−0.2367	0.063*
H11B	−0.2094	−1.0467	−0.1542	0.063*
H11C	−0.0400	−1.1383	−0.1609	0.063*
N1	0.4973 (3)	−0.2479 (3)	0.23935 (11)	0.0383 (6)
H1A	0.550 (3)	−0.192 (3)	0.2748 (12)	0.038*
H1B	0.454 (3)	−0.340 (3)	0.2485 (12)	0.038*
O1	0.56177 (16)	−0.04310 (18)	0.15705 (7)	0.0292 (4)
O2	0.32315 (19)	−0.51874 (18)	0.14725 (8)	0.0377 (4)
O3	0.27143 (17)	−0.47150 (17)	0.01739 (8)	0.0324 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0243 (13)	0.0246 (14)	0.0275 (12)	0.0019 (10)	0.0017 (10)	−0.0028 (10)
C2	0.0267 (12)	0.0283 (14)	0.0184 (11)	0.0051 (11)	0.0018 (9)	0.0001 (10)
C3	0.0225 (12)	0.0268 (14)	0.0271 (12)	0.0040 (10)	0.0039 (10)	−0.0032 (10)
C4	0.0263 (12)	0.0216 (13)	0.0271 (12)	0.0021 (10)	0.0009 (10)	−0.0009 (10)
C5	0.0289 (13)	0.0252 (15)	0.0303 (13)	0.0008 (11)	0.0039 (10)	0.0012 (11)
C6	0.0260 (13)	0.0305 (15)	0.0286 (13)	0.0076 (11)	−0.0001 (10)	−0.0006 (11)
C7	0.0304 (13)	0.0269 (14)	0.0400 (14)	−0.0019 (11)	0.0041 (11)	−0.0014 (11)
C8	0.0282 (13)	0.0345 (16)	0.0385 (13)	0.0024 (11)	0.0029 (11)	−0.0043 (11)
C9	0.0292 (13)	0.0355 (16)	0.0487 (15)	0.0032 (11)	0.0025 (12)	−0.0065 (12)
C10	0.0432 (16)	0.0499 (18)	0.0483 (15)	−0.0056 (14)	0.0068 (13)	−0.0135 (13)
C11	0.0620 (19)	0.054 (2)	0.073 (2)	−0.0181 (16)	0.0085 (16)	−0.0242 (15)
N1	0.0530 (14)	0.0320 (14)	0.0268 (12)	−0.0109 (11)	−0.0033 (10)	0.0022 (10)
O1	0.0350 (9)	0.0296 (10)	0.0224 (8)	−0.0013 (7)	0.0025 (7)	0.0006 (7)
O2	0.0489 (10)	0.0313 (10)	0.0307 (9)	−0.0033 (8)	−0.0003 (7)	0.0075 (7)
O3	0.0373 (9)	0.0293 (10)	0.0289 (9)	−0.0043 (7)	0.0001 (7)	−0.0010 (7)

C1—C2	1.393 (3)	C7—H7B	0.9900
C1—C3i	1.422 (3)	C8—C9	1.549 (3)
C1—H1	1.0231	C8—H8A	0.9900
C2—C3	1.418 (3)	C8—H8B	0.9900
C2—O1	1.419 (2)	C9—C10	1.540 (3)
C3—C1i	1.422 (3)	C9—H9A	0.9900
C3—C4	1.477 (3)	C9—H9B	0.9900
C4—C5	1.394 (3)	C10—C11	1.543 (3)
C4—C6	1.457 (3)	C10—H10A	0.9900
C5—N1	1.338 (3)	C10—H10B	0.9900
C5—O1	1.384 (2)	C11—H11A	0.9800
C6—O2	1.247 (2)	C11—H11B	0.9800
C6—O3	1.369 (2)	C11—H11C	0.9800
C7—O3	1.479 (2)	N1—H1A	0.83 (2)
C7—C8	1.518 (3)	N1—H1B	0.84 (2)
C7—H7A	0.9900
C2—C1—C3i	114.40 (18)	C7—C8—H8B	109.5
C2—C1—H1	127.3	C9—C8—H8B	109.5
C3i—C1—H1	118.3	H8A—C8—H8B	108.1
C1—C2—C3	126.93 (18)	C10—C9—C8	114.01 (19)
C1—C2—O1	123.44 (18)	C10—C9—H9A	108.8
C3—C2—O1	109.63 (17)	C8—C9—H9A	108.8
C2—C3—C1i	118.67 (18)	C10—C9—H9B	108.8
C2—C3—C4	106.02 (17)	C8—C9—H9B	108.8
C1i—C3—C4	135.31 (19)	H9A—C9—H9B	107.6
C5—C4—C6	122.45 (19)	C9—C10—C11	112.2 (2)
C5—C4—C3	105.72 (18)	C9—C10—H10A	109.2
C6—C4—C3	131.82 (18)	C11—C10—H10A	109.2
N1—C5—O1	115.50 (19)	C9—C10—H10B	109.2
N1—C5—C4	132.4 (2)	C11—C10—H10B	109.2
O1—C5—C4	112.08 (18)	H10A—C10—H10B	107.9
O2—C6—O3	121.9 (2)	C10—C11—H11A	109.5
O2—C6—C4	124.58 (19)	C10—C11—H11B	109.5
O3—C6—C4	113.54 (18)	H11A—C11—H11B	109.5
O3—C7—C8	109.05 (16)	C10—C11—H11C	109.5
O3—C7—H7A	109.9	H11A—C11—H11C	109.5
C8—C7—H7A	109.9	H11B—C11—H11C	109.5
O3—C7—H7B	109.9	C5—N1—H1A	119.4 (15)
C8—C7—H7B	109.9	C5—N1—H1B	119.5 (15)
H7A—C7—H7B	108.3	H1A—N1—H1B	121 (2)
C7—C8—C9	110.81 (18)	C5—O1—C2	106.54 (16)
C7—C8—H8A	109.5	C6—O3—C7	115.84 (15)
C9—C8—H8A	109.5
C3i—C1—C2—C3	0.1 (3)	C5—C4—C6—O2	−0.8 (3)
C3i—C1—C2—O1	179.41 (17)	C3—C4—C6—O2	178.5 (2)
C1—C2—C3—C1i	−0.1 (3)	C5—C4—C6—O3	179.06 (18)
O1—C2—C3—C1i	−179.49 (16)	C3—C4—C6—O3	−1.6 (3)
C1—C2—C3—C4	179.22 (19)	O3—C7—C8—C9	−178.43 (16)
O1—C2—C3—C4	−0.2 (2)	C7—C8—C9—C10	−179.49 (19)
C2—C3—C4—C5	0.7 (2)	C8—C9—C10—C11	179.2 (2)
C1i—C3—C4—C5	179.8 (2)	N1—C5—O1—C2	−178.64 (17)
C2—C3—C4—C6	−178.7 (2)	C4—C5—O1—C2	0.8 (2)
C1i—C3—C4—C6	0.4 (4)	C1—C2—O1—C5	−179.79 (18)
C6—C4—C5—N1	−2.1 (4)	C3—C2—O1—C5	−0.3 (2)
C3—C4—C5—N1	178.4 (2)	O2—C6—O3—C7	−0.4 (3)
C6—C4—C5—O1	178.55 (17)	C4—C6—O3—C7	179.72 (16)
C3—C4—C5—O1	−0.9 (2)	C8—C7—O3—C6	−178.24 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ii	0.83 (2)	2.11 (2)	2.935 (3)	171 (2)
N1—H1B···O1iii	0.84 (2)	2.34 (2)	3.066 (2)	144 (2)
N1—H1B···O2	0.84 (2)	2.41 (2)	2.942 (3)	122.2 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.83 (2)	2.11 (2)	2.935 (3)	171 (2)
N1—H1B⋯O1ii	0.84 (2)	2.34 (2)	3.066 (2)	144 (2)
N1—H1B⋯O2	0.84 (2)	2.41 (2)	2.942 (3)	122.2 (18)

Symmetry codes: (i) ; (ii) .