Methyl 2-amino-4,5-di-meth-oxy-benzoate.

The title compound, C10H13NO4, is essentially planar, with an r.m.s. deviation of 0.049 Å. An intra-molecular C-H⋯O hydrogen bond occurs and the amino group forms an intra-molecular N-H⋯Oester hydrogen bond; the other H atom forms an inter-molecular N-H⋯Ocarbon-yl hydrogen bond, leading to the formation of a helical chain that runs along the b-axis direction.

Related literature

For similar crystal structures, see: Zhang et al. (2009 ▶); Smith & Elsegood (2002 ▶).

Experimental

Crystal data

C10H13NO4

M = 211.21

Monoclinic,

a = 11.1933 (4) Å

b = 7.7564 (3) Å

c = 13.7728 (5) Å

β = 121.741 (2)°

V = 1016.91 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 173 K

0.5 × 0.29 × 0.25 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.948, T max = 0.974

9994 measured reflections

2543 independent reflections

2080 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.109

S = 1.05

2543 reflections

147 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012) ▶.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813030894/ng5347sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813030894/ng5347Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813030894/ng5347Isup3.cml

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

C10H13NO4	F(000) = 448
Mr = 211.21	Dx = 1.38 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3834 reflections
a = 11.1933 (4) Å	θ = 3.0–28.3°
b = 7.7564 (3) Å	µ = 0.11 mm−1
c = 13.7728 (5) Å	T = 173 K
β = 121.741 (2)°	Cuboid, yellow
V = 1016.91 (7) Å3	0.5 × 0.29 × 0.25 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2543 independent reflections
Radiation source: fine-focus sealed tube	2080 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 512 pixels mm-1	θmax = 28.3°, θmin = 2.1°
ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −10→10
Tmin = 0.948, Tmax = 0.974	l = −18→18
9994 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.038	w = 1/[σ2(Fo2) + (0.0501P)2 + 0.2646P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.109	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.27 e Å−3
2543 reflections	Δρmin = −0.25 e Å−3
147 parameters

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.

	x	y	z	Uiso*/Ueq
C1	0.19769 (12)	0.09141 (14)	−0.01177 (10)	0.0237 (2)
C2	0.16865 (12)	0.16680 (14)	−0.11496 (10)	0.0243 (2)
C3	0.22538 (12)	0.33134 (15)	−0.11104 (10)	0.0250 (2)
H3	0.2062	0.3839	−0.1801	0.03*
C4	0.30761 (12)	0.41704 (14)	−0.00949 (10)	0.0239 (2)
C5	0.33814 (12)	0.34050 (14)	0.09484 (9)	0.0234 (2)
C6	0.28295 (12)	0.18137 (14)	0.09202 (9)	0.0235 (2)
H6	0.3024	0.1301	0.1615	0.028*
C7	0.13820 (12)	−0.07648 (14)	−0.01151 (10)	0.0256 (2)
C8	0.13103 (15)	−0.30520 (15)	0.09811 (12)	0.0340 (3)
H8A	0.0291	−0.3006	0.064	0.051*
H8B	0.1763	−0.3421	0.1779	0.051*
H8C	0.1531	−0.3875	0.0558	0.051*
C9	0.33489 (15)	0.66056 (17)	−0.10146 (11)	0.0345 (3)
H9A	0.3706	0.591	−0.1402	0.052*
H9B	0.3805	0.7738	−0.0826	0.052*
H9C	0.2331	0.6751	−0.1518	0.052*
C10	0.44564 (14)	0.36738 (17)	0.29532 (10)	0.0328 (3)
H10A	0.3554	0.3526	0.29	0.049*
H10B	0.5049	0.4467	0.3579	0.049*
H10C	0.4927	0.2554	0.31	0.049*
N1	0.09141 (12)	0.08643 (15)	−0.21889 (9)	0.0326 (3)
O1	0.05611 (10)	−0.15847 (12)	−0.09659 (8)	0.0376 (2)
O2	0.18202 (10)	−0.13617 (11)	0.09315 (7)	0.0324 (2)
O3	0.36486 (9)	0.57535 (10)	0.00121 (7)	0.0293 (2)
O4	0.42222 (9)	0.43624 (10)	0.19078 (7)	0.0279 (2)
H1B	0.0560 (16)	0.1496 (19)	−0.2812 (14)	0.037 (4)*
H1A	0.0410 (18)	−0.007 (3)	−0.2225 (15)	0.056 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0235 (5)	0.0231 (5)	0.0239 (5)	0.0032 (4)	0.0121 (4)	−0.0001 (4)
C2	0.0221 (5)	0.0261 (5)	0.0232 (5)	0.0050 (4)	0.0110 (4)	−0.0010 (4)
C3	0.0261 (6)	0.0278 (6)	0.0223 (5)	0.0056 (4)	0.0137 (5)	0.0038 (4)
C4	0.0248 (6)	0.0229 (5)	0.0268 (5)	0.0033 (4)	0.0155 (5)	0.0024 (4)
C5	0.0236 (5)	0.0249 (5)	0.0219 (5)	0.0017 (4)	0.0121 (4)	−0.0004 (4)
C6	0.0255 (6)	0.0237 (5)	0.0216 (5)	0.0021 (4)	0.0127 (4)	0.0011 (4)
C7	0.0250 (6)	0.0246 (5)	0.0272 (6)	0.0032 (4)	0.0137 (5)	−0.0011 (4)
C8	0.0438 (8)	0.0221 (5)	0.0417 (7)	−0.0015 (5)	0.0263 (6)	0.0015 (5)
C9	0.0402 (7)	0.0328 (6)	0.0336 (6)	0.0003 (5)	0.0214 (6)	0.0092 (5)
C10	0.0398 (7)	0.0348 (6)	0.0218 (6)	−0.0095 (5)	0.0148 (5)	−0.0019 (5)
N1	0.0371 (6)	0.0324 (6)	0.0211 (5)	−0.0008 (5)	0.0102 (5)	−0.0008 (4)
O1	0.0411 (5)	0.0323 (5)	0.0305 (5)	−0.0088 (4)	0.0127 (4)	−0.0055 (4)
O2	0.0431 (5)	0.0241 (4)	0.0295 (4)	−0.0050 (4)	0.0188 (4)	−0.0004 (3)
O3	0.0363 (5)	0.0258 (4)	0.0271 (4)	−0.0031 (3)	0.0176 (4)	0.0029 (3)
O4	0.0341 (5)	0.0271 (4)	0.0215 (4)	−0.0063 (3)	0.0140 (4)	−0.0018 (3)

C1—C2	1.4077 (15)	C8—O2	1.4458 (14)
C1—C6	1.4162 (15)	C8—H8A	0.98
C1—C7	1.4634 (16)	C8—H8B	0.98
C2—N1	1.3722 (15)	C8—H8C	0.98
C2—C3	1.4138 (16)	C9—O3	1.4317 (14)
C3—C4	1.3751 (16)	C9—H9A	0.98
C3—H3	0.95	C9—H9B	0.98
C4—O3	1.3568 (13)	C9—H9C	0.98
C4—C5	1.4203 (15)	C10—O4	1.4247 (14)
C5—O4	1.3692 (13)	C10—H10A	0.98
C5—C6	1.3716 (15)	C10—H10B	0.98
C6—H6	0.95	C10—H10C	0.98
C7—O1	1.2202 (14)	N1—H1B	0.881 (16)
C7—O2	1.3374 (14)	N1—H1A	0.90 (2)
C2—C1—C6	119.31 (10)	H8A—C8—H8B	109.5
C2—C1—C7	120.56 (10)	O2—C8—H8C	109.5
C6—C1—C7	120.12 (10)	H8A—C8—H8C	109.5
N1—C2—C1	123.27 (11)	H8B—C8—H8C	109.5
N1—C2—C3	118.28 (10)	O3—C9—H9A	109.5
C1—C2—C3	118.42 (10)	O3—C9—H9B	109.5
C4—C3—C2	121.47 (10)	H9A—C9—H9B	109.5
C4—C3—H3	119.3	O3—C9—H9C	109.5
C2—C3—H3	119.3	H9A—C9—H9C	109.5
O3—C4—C3	124.97 (10)	H9B—C9—H9C	109.5
O3—C4—C5	114.83 (10)	O4—C10—H10A	109.5
C3—C4—C5	120.20 (10)	O4—C10—H10B	109.5
O4—C5—C6	125.87 (10)	H10A—C10—H10B	109.5
O4—C5—C4	115.28 (10)	O4—C10—H10C	109.5
C6—C5—C4	118.85 (10)	H10A—C10—H10C	109.5
C5—C6—C1	121.75 (10)	H10B—C10—H10C	109.5
C5—C6—H6	119.1	C2—N1—H1B	118.5 (10)
C1—C6—H6	119.1	C2—N1—H1A	117.0 (12)
O1—C7—O2	121.23 (11)	H1B—N1—H1A	116.4 (15)
O1—C7—C1	125.11 (11)	C7—O2—C8	115.77 (9)
O2—C7—C1	113.66 (10)	C4—O3—C9	117.30 (9)
O2—C8—H8A	109.5	C5—O4—C10	116.08 (9)
O2—C8—H8B	109.5
C6—C1—C2—N1	177.57 (11)	C4—C5—C6—C1	0.54 (17)
C7—C1—C2—N1	−3.72 (17)	C2—C1—C6—C5	0.06 (17)
C6—C1—C2—C3	−0.46 (16)	C7—C1—C6—C5	−178.65 (10)
C7—C1—C2—C3	178.25 (10)	C2—C1—C7—O1	−3.96 (18)
N1—C2—C3—C4	−177.87 (11)	C6—C1—C7—O1	174.73 (11)
C1—C2—C3—C4	0.26 (16)	C2—C1—C7—O2	176.09 (10)
C2—C3—C4—O3	−179.49 (10)	C6—C1—C7—O2	−5.22 (15)
C2—C3—C4—C5	0.33 (17)	O1—C7—O2—C8	2.67 (16)
O3—C4—C5—O4	−0.88 (14)	C1—C7—O2—C8	−177.38 (10)
C3—C4—C5—O4	179.28 (10)	C3—C4—O3—C9	1.26 (16)
O3—C4—C5—C6	179.10 (10)	C5—C4—O3—C9	−178.57 (10)
C3—C4—C5—C6	−0.73 (17)	C6—C5—O4—C10	−4.40 (16)
O4—C5—C6—C1	−179.48 (10)	C4—C5—O4—C10	175.59 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2	0.95	2.37	2.7131 (14)	101
N1—H1A···O1	0.90 (2)	2.03 (2)	2.702 (2)	131 (2)
N1—H1B···O1i	0.88 (2)	2.10 (2)	2.947 (1)	162 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2	0.95	2.37	2.7131 (14)	101
N1—H1A⋯O1	0.90 (2)	2.03 (2)	2.702 (2)	131 (2)
N1—H1B⋯O1i	0.88 (2)	2.10 (2)	2.947 (1)	162 (1)

Symmetry code: (i) .