Di-n-butyl 5-amino-isophthalate.

The title compound, C(16)H(23)NO(4), is essentially planar except for the last two C atoms in each n-butyl group (r.m.s. deviation from the least-squares plane = 0.02 Å for 17 non-H atoms). In the crystal, inter-molecular N-H⋯O hydrogen bonds between the amine and carbonyl groups link the mol-ecules into one-dimensional chains.

Related literature

For the related structure of 5-amino­isophthalic acid hemihydrate, see: Dobson & Gerkin (1998 ▶).

Experimental

Crystal data

C16H23NO4

M = 293.35

Monoclinic,

a = 9.4350 (19) Å

b = 9.1640 (18) Å

c = 20.166 (4) Å

β = 94.67 (3)°

V = 1737.8 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.991, T max = 0.994

8863 measured reflections

3169 independent reflections

1612 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.221

S = 1.04

3169 reflections

196 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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 datablocks global, I. DOI: 10.1107/S1600536809024696/bi2379sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024696/bi2379Isup2.hkl

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

C16H23NO4	F(000) = 632
Mr = 293.35	Dx = 1.121 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3119 reflections
a = 9.4350 (19) Å	θ = 2.0–25.5°
b = 9.1640 (18) Å	µ = 0.08 mm−1
c = 20.166 (4) Å	T = 296 K
β = 94.67 (3)°	Block, colourless
V = 1737.8 (6) Å3	0.12 × 0.10 × 0.08 mm
Z = 4

Bruker APEXII CCD diffractometer	3169 independent reflections
Radiation source: fine-focus sealed tube	1612 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 25.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→11
Tmin = 0.991, Tmax = 0.994	k = −11→10
8863 measured reflections	l = −24→23

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.221	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.1119P)2 + 0.1542P] where P = (Fo2 + 2Fc2)/3
3169 reflections	(Δ/σ)max < 0.001
196 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.8685 (2)	0.3309 (2)	0.44186 (12)	0.1051 (8)
O2	0.6509 (2)	0.3015 (2)	0.39278 (11)	0.0938 (7)
O3	0.3317 (2)	0.8767 (3)	0.44890 (13)	0.1092 (8)
O4	0.29283 (19)	0.6651 (2)	0.39827 (11)	0.0944 (7)
N1	0.8560 (3)	0.8512 (4)	0.5269 (2)	0.1380 (15)
H1A	0.933 (6)	0.815 (7)	0.540 (3)	0.207*
H1B	0.831 (6)	0.926 (6)	0.546 (3)	0.207*
C1	0.7518 (3)	0.3783 (3)	0.42708 (14)	0.0759 (8)
C2	0.7015 (2)	0.5250 (3)	0.44442 (12)	0.0674 (7)
C3	0.7986 (3)	0.6180 (3)	0.47724 (14)	0.0768 (8)
H3A	0.8917	0.5868	0.4872	0.092*
C4	0.7598 (3)	0.7572 (3)	0.49558 (15)	0.0856 (9)
C5	0.6193 (3)	0.8002 (3)	0.47979 (15)	0.0808 (8)
H5A	0.5905	0.8928	0.4919	0.097*
C6	0.5223 (3)	0.7080 (3)	0.44666 (13)	0.0681 (7)
C7	0.5629 (3)	0.5693 (3)	0.42860 (12)	0.0675 (7)
H7A	0.4977	0.5068	0.4062	0.081*
C8	0.3749 (3)	0.7609 (3)	0.43193 (15)	0.0784 (8)
C9	0.1463 (3)	0.7056 (4)	0.38233 (19)	0.1024 (10)
H9A	0.1406	0.7901	0.3533	0.123*
H9B	0.1017	0.7296	0.4226	0.123*
C10	0.0741 (4)	0.5806 (5)	0.3489 (3)	0.1371 (16)
H10A	0.0657	0.5054	0.3822	0.165*
H10B	−0.0218	0.6115	0.3344	0.165*
C11	0.1293 (6)	0.5169 (9)	0.2960 (4)	0.220 (3)
H11A	0.2257	0.4870	0.3101	0.265*
H11B	0.1358	0.5912	0.2621	0.265*
C12	0.0559 (7)	0.3906 (9)	0.2644 (5)	0.300 (6)
H12A	0.1046	0.3602	0.2267	0.450*
H12B	−0.0401	0.4170	0.2499	0.450*
H12C	0.0553	0.3119	0.2958	0.450*
C13	0.6881 (4)	0.1552 (3)	0.3734 (2)	0.1112 (11)
H13A	0.7234	0.0992	0.4121	0.133*
H13B	0.7614	0.1584	0.3424	0.133*
C14	0.5572 (5)	0.0874 (4)	0.3415 (3)	0.1471 (16)
H14A	0.5822	−0.0100	0.3277	0.177*
H14B	0.4913	0.0762	0.3757	0.177*
C15	0.4815 (6)	0.1559 (6)	0.2858 (3)	0.175 (2)
H15A	0.5447	0.1639	0.2504	0.210*
H15B	0.4570	0.2542	0.2986	0.210*
C16	0.3471 (6)	0.0794 (7)	0.2586 (3)	0.205 (3)
H16A	0.3044	0.1331	0.2212	0.307*
H16B	0.2817	0.0740	0.2926	0.307*
H16C	0.3698	−0.0173	0.2447	0.307*

	U11	U22	U33	U12	U13	U23
O1	0.0690 (13)	0.0819 (14)	0.160 (2)	0.0183 (10)	−0.0158 (13)	−0.0206 (13)
O2	0.0795 (13)	0.0724 (13)	0.1264 (16)	0.0090 (10)	−0.0112 (11)	−0.0208 (11)
O3	0.0665 (12)	0.0882 (15)	0.169 (2)	0.0181 (11)	−0.0143 (12)	−0.0307 (14)
O4	0.0608 (11)	0.0900 (14)	0.1280 (17)	0.0102 (10)	−0.0193 (10)	−0.0165 (12)
N1	0.0748 (18)	0.093 (2)	0.237 (4)	0.0125 (15)	−0.046 (2)	−0.060 (2)
C1	0.0668 (17)	0.0684 (17)	0.0917 (19)	0.0034 (14)	0.0007 (14)	−0.0048 (14)
C2	0.0591 (14)	0.0654 (15)	0.0775 (16)	0.0036 (12)	0.0031 (12)	0.0013 (12)
C3	0.0570 (14)	0.0715 (18)	0.0993 (19)	0.0082 (12)	−0.0090 (13)	−0.0062 (14)
C4	0.0631 (16)	0.0731 (19)	0.117 (2)	0.0039 (14)	−0.0137 (15)	−0.0129 (16)
C5	0.0621 (16)	0.0667 (16)	0.111 (2)	0.0084 (13)	−0.0059 (14)	−0.0116 (15)
C6	0.0563 (14)	0.0651 (16)	0.0821 (17)	0.0020 (12)	−0.0004 (12)	0.0021 (13)
C7	0.0604 (15)	0.0667 (16)	0.0747 (16)	0.0012 (12)	0.0006 (12)	0.0007 (12)
C8	0.0611 (15)	0.0721 (19)	0.100 (2)	0.0036 (14)	−0.0054 (14)	−0.0018 (15)
C9	0.0600 (17)	0.119 (3)	0.123 (2)	0.0091 (17)	−0.0191 (16)	−0.007 (2)
C10	0.080 (2)	0.156 (4)	0.168 (4)	0.000 (2)	−0.030 (2)	−0.036 (3)
C11	0.127 (4)	0.280 (8)	0.248 (7)	−0.001 (5)	−0.022 (4)	−0.138 (7)
C12	0.173 (6)	0.301 (10)	0.410 (13)	−0.007 (5)	−0.074 (6)	−0.230 (10)
C13	0.114 (3)	0.073 (2)	0.143 (3)	0.0126 (18)	−0.009 (2)	−0.0249 (19)
C14	0.155 (4)	0.088 (3)	0.190 (4)	0.007 (2)	−0.038 (3)	−0.042 (3)
C15	0.168 (4)	0.148 (4)	0.197 (5)	0.010 (3)	−0.052 (4)	−0.041 (4)
C16	0.140 (4)	0.228 (6)	0.235 (6)	−0.002 (4)	−0.053 (4)	−0.094 (5)

O1—C1	1.198 (3)	C9—H9B	0.970
O2—C1	1.331 (3)	C10—C11	1.357 (6)
O2—C13	1.448 (4)	C10—H10A	0.970
O3—C8	1.197 (3)	C10—H10B	0.970
O4—C8	1.321 (3)	C11—C12	1.468 (8)
O4—C9	1.442 (3)	C11—H11A	0.970
N1—C4	1.368 (4)	C11—H11B	0.970
N1—H1A	0.83 (5)	C12—H12A	0.960
N1—H1B	0.83 (6)	C12—H12B	0.960
C1—C2	1.478 (4)	C12—H12C	0.960
C2—C3	1.380 (4)	C13—C14	1.481 (5)
C2—C7	1.382 (3)	C13—H13A	0.970
C3—C4	1.385 (4)	C13—H13B	0.970
C3—H3A	0.930	C14—C15	1.426 (7)
C4—C5	1.395 (4)	C14—H14A	0.970
C5—C6	1.377 (4)	C14—H14B	0.970
C5—H5A	0.930	C15—C16	1.513 (7)
C6—C7	1.385 (3)	C15—H15A	0.970
C6—C8	1.480 (4)	C15—H15B	0.970
C7—H7A	0.930	C16—H16A	0.960
C9—C10	1.468 (5)	C16—H16B	0.960
C9—H9A	0.970	C16—H16C	0.960
C1—O2—C13	116.8 (2)	C9—C10—H10B	107.3
C8—O4—C9	117.0 (2)	H10A—C10—H10B	106.9
C4—N1—H1A	116 (4)	C10—C11—C12	118.9 (7)
C4—N1—H1B	122 (4)	C10—C11—H11A	107.6
H1A—N1—H1B	117 (5)	C12—C11—H11A	107.6
O1—C1—O2	122.8 (2)	C10—C11—H11B	107.6
O1—C1—C2	125.3 (3)	C12—C11—H11B	107.6
O2—C1—C2	112.0 (2)	H11A—C11—H11B	107.0
C3—C2—C7	120.6 (2)	C11—C12—H12A	109.5
C3—C2—C1	117.5 (2)	C11—C12—H12B	109.5
C7—C2—C1	121.9 (2)	H12A—C12—H12B	109.5
C2—C3—C4	121.1 (2)	C11—C12—H12C	109.5
C2—C3—H3A	119.4	H12A—C12—H12C	109.5
C4—C3—H3A	119.4	H12B—C12—H12C	109.5
N1—C4—C3	121.5 (2)	O2—C13—C14	107.1 (3)
N1—C4—C5	120.7 (3)	O2—C13—H13A	110.3
C3—C4—C5	117.8 (2)	C14—C13—H13A	110.3
C6—C5—C4	121.3 (3)	O2—C13—H13B	110.3
C6—C5—H5A	119.4	C14—C13—H13B	110.3
C4—C5—H5A	119.4	H13A—C13—H13B	108.6
C5—C6—C7	120.2 (2)	C15—C14—C13	120.2 (5)
C5—C6—C8	118.2 (2)	C15—C14—H14A	107.3
C7—C6—C8	121.5 (2)	C13—C14—H14A	107.3
C2—C7—C6	119.0 (2)	C15—C14—H14B	107.3
C2—C7—H7A	120.5	C13—C14—H14B	107.3
C6—C7—H7A	120.5	H14A—C14—H14B	106.9
O3—C8—O4	122.5 (2)	C14—C15—C16	115.7 (5)
O3—C8—C6	124.7 (3)	C14—C15—H15A	108.4
O4—C8—C6	112.8 (3)	C16—C15—H15A	108.4
O4—C9—C10	107.6 (3)	C14—C15—H15B	108.4
O4—C9—H9A	110.2	C16—C15—H15B	108.4
C10—C9—H9A	110.2	H15A—C15—H15B	107.4
O4—C9—H9B	110.2	C15—C16—H16A	109.5
C10—C9—H9B	110.2	C15—C16—H16B	109.5
H9A—C9—H9B	108.5	H16A—C16—H16B	109.5
C11—C10—C9	120.2 (4)	C15—C16—H16C	109.5
C11—C10—H10A	107.3	H16A—C16—H16C	109.5
C9—C10—H10A	107.3	H16B—C16—H16C	109.5
C11—C10—H10B	107.3
C13—O2—C1—O1	−0.1 (5)	C1—C2—C7—C6	179.6 (2)
C13—O2—C1—C2	−179.6 (3)	C5—C6—C7—C2	0.1 (4)
O1—C1—C2—C3	3.6 (4)	C8—C6—C7—C2	−179.1 (2)
O2—C1—C2—C3	−176.9 (2)	C9—O4—C8—O3	0.0 (4)
O1—C1—C2—C7	−176.5 (3)	C9—O4—C8—C6	179.1 (2)
O2—C1—C2—C7	3.0 (4)	C5—C6—C8—O3	−2.9 (5)
C7—C2—C3—C4	0.5 (4)	C7—C6—C8—O3	176.4 (3)
C1—C2—C3—C4	−179.6 (3)	C5—C6—C8—O4	178.0 (2)
C2—C3—C4—N1	−178.7 (3)	C7—C6—C8—O4	−2.7 (4)
C2—C3—C4—C5	0.0 (4)	C8—O4—C9—C10	−176.6 (3)
N1—C4—C5—C6	178.2 (3)	O4—C9—C10—C11	−51.7 (6)
C3—C4—C5—C6	−0.4 (5)	C9—C10—C11—C12	179.0 (7)
C4—C5—C6—C7	0.4 (4)	C1—O2—C13—C14	175.1 (3)
C4—C5—C6—C8	179.6 (3)	O2—C13—C14—C15	56.2 (6)
C3—C2—C7—C6	−0.5 (4)	C13—C14—C15—C16	−178.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.83 (5)	2.30 (6)	3.110 (4)	165 (6)
N1—H1B···O3ii	0.83 (6)	2.38 (6)	3.120 (4)	149 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.83 (5)	2.30 (6)	3.110 (4)	165 (6)
N1—H1B⋯O3ii	0.83 (6)	2.38 (6)	3.120 (4)	149 (5)

Symmetry codes: (i) ; (ii) .