Methyl 2-(4-meth­oxy-3-nitro­benzamido)­acetate

Zhu, X.; Ma, Q.

doi:10.1107/S1600536812029522

organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2343

https://doi.org/10.1107/S1600536812029522

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Methyl 2-(4-methoxy-3-nitrobenzamido)acetate

Xin Zhu ^a ^* and Qiujuan Ma ^a

^aCollege of Pharmacy, Henan University of Traditional Chinese Medicine, Zhengzhou, Henan 450008, People's Republic of China
^*Correspondence e-mail: xerz2@126.com

(Received 3 June 2012; accepted 28 June 2012; online 4 July 2012)

The title compound, C₁₁H₁₂N₂O₆, crystallizes with two independent molecules in the asymmetric unit, which differ slightly in conformation. The dihedral angle between the amide O=C—N plane and the attached benzene ring is 19.5 (3)° in one molecule and 23.4 (3)° in the other. In the crystal, the two independent molecules are connected alternately by N—H⋯O hydrogen bonds, forming a chain along the a axis.

Related literature

For the biological activity of compounds with nitro and ester groups, see: Sykes et al. (1999 ). For a related structure, see: Wu et al. (2011 ).

Experimental

Crystal data

C₁₁H₁₂N₂O₆
M_r = 268.23
Monoclinic, P 2₁ /c
a = 10.4378 (7) Å
b = 13.9110 (9) Å
c = 17.5420 (15) Å
β = 106.146 (8)°
V = 2446.6 (3) Å³
Z = 8
Cu Kα radiation
μ = 1.04 mm⁻¹
T = 291 K
0.28 × 0.26 × 0.24 mm

Data collection

Agilent Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.760, T_max = 0.789
10600 measured reflections
4251 independent reflections
3287 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.155
S = 1.04
4251 reflections
356 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4′ⁱ	0.83 (2)	2.26 (2)	3.069 (2)	167 (2)
N2′—H2′⋯O4	0.83 (2)	2.23 (2)	3.016 (2)	158 (2)
Symmetry code: (i) x+1, y, z.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812029522/is5151sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812029522/is5151Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812029522/is5151Isup3.cml

checkCIF report

Comment top

The nitro group and ester group are present in many bioactive compounds or be used as prodrug (Sykes et al., 1999). Here we report the crystal structure of C₁₁H₁₂N₂O₆, namely, methyl 2-(4-methoxy-3-nitrobenzamido)acetate. In the crystal of the title compound (Fig. 1), the carbonyl group and the adjacent amide group are connected by intermolecular N—H···O hydrogen bonds, forming a chain along the a axis (Fig. 2).

Related literature top

For the biological activity of compounds with nitro and ester groups, see: Sykes et al. (1999). For a related structure, see: Wu et al. (2011).

Experimental top

The title compound (0.25 mmol, 67.0 mg) was dissolved in water-methanol (1 ml / 2 ml v/v) mixture. Colorless block crystals were separated after several weeks.

Structure description top

For the biological activity of compounds with nitro and ester groups, see: Sykes et al. (1999). For a related structure, see: Wu et al. (2011).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis RED (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. A view of the molecular structure of the title compound The displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of the hydrogen bonded polymeric chain. The hydrogen bonds are shown as dashed lines.

Methyl 2-(4-methoxy-3-nitrobenzamido)acetate top

Crystal data top

C₁₁H₁₂N₂O₆	F(000) = 1120
M_r = 268.23	D_x = 1.456 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 3206 reflections
a = 10.4378 (7) Å	θ = 3.2–67.0°
b = 13.9110 (9) Å	µ = 1.03 mm⁻¹
c = 17.5420 (15) Å	T = 291 K
β = 106.146 (8)°	Block, colorless
V = 2446.6 (3) Å³	0.28 × 0.26 × 0.24 mm
Z = 8

Data collection top

Agilent Xcalibur Eos Gemini diffractometer	4251 independent reflections
Radiation source: fine-focus sealed tube	3287 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 67.0°, θ_min = 4.1°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −12→12
T_min = 0.760, T_max = 0.789	k = −16→16
10600 measured reflections	l = −20→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.155	w = 1/[σ²(F_o²) + (0.073P)² + 0.8379P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.004
4251 reflections	Δρ_max = 0.50 e Å⁻³
356 parameters	Δρ_min = −0.31 e Å⁻³
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00093 (17)

Crystal data top

C₁₁H₁₂N₂O₆	V = 2446.6 (3) Å³
M_r = 268.23	Z = 8
Monoclinic, P2₁/c	Cu Kα radiation
a = 10.4378 (7) Å	µ = 1.03 mm⁻¹
b = 13.9110 (9) Å	T = 291 K
c = 17.5420 (15) Å	0.28 × 0.26 × 0.24 mm
β = 106.146 (8)°

Data collection top

Agilent Xcalibur Eos Gemini diffractometer	4251 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	3287 reflections with I > 2σ(I)
T_min = 0.760, T_max = 0.789	R_int = 0.026
10600 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	2 restraints
wR(F²) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.50 e Å⁻³
4251 reflections	Δρ_min = −0.31 e Å⁻³
356 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.7104 (2)	0.31701 (14)	0.29328 (12)	0.0732 (6)
O1'	0.18346 (19)	1.11580 (13)	0.30677 (12)	0.0671 (5)
O2	0.9503 (2)	0.31213 (17)	0.3839 (2)	0.1162 (11)
O2'	0.4242 (2)	1.12599 (15)	0.40786 (18)	0.0981 (9)
O3	1.0472 (2)	0.44345 (17)	0.41534 (18)	0.1013 (9)
O3'	0.5286 (2)	0.99534 (16)	0.41347 (19)	0.1039 (9)
O4	0.58759 (15)	0.72298 (13)	0.42220 (11)	0.0593 (5)
O4'	0.09322 (15)	0.69905 (12)	0.43303 (11)	0.0576 (5)
O5	0.7439 (2)	0.90062 (15)	0.34121 (12)	0.0724 (6)
O5'	0.2464 (2)	0.54205 (14)	0.32784 (11)	0.0677 (5)
O6	0.82081 (18)	0.99909 (13)	0.44488 (13)	0.0688 (5)
O6'	0.33449 (16)	0.43396 (11)	0.42284 (11)	0.0563 (4)
N1	0.9474 (2)	0.39794 (16)	0.38787 (13)	0.0579 (5)
N1'	0.4254 (2)	1.04059 (14)	0.39950 (14)	0.0569 (5)
N2	0.80857 (19)	0.74112 (15)	0.44094 (13)	0.0523 (5)
N2'	0.31167 (18)	0.68992 (14)	0.43984 (12)	0.0473 (5)
C1	0.7024 (2)	0.40601 (18)	0.32103 (14)	0.0530 (6)
C1'	0.1806 (2)	1.02642 (16)	0.33482 (14)	0.0483 (5)
C2	0.8203 (2)	0.44932 (17)	0.36718 (13)	0.0457 (5)
C2'	0.3009 (2)	0.98568 (16)	0.38040 (14)	0.0454 (5)
C3	0.8207 (2)	0.54128 (17)	0.39638 (13)	0.0443 (5)
H3	0.9007	0.5688	0.4253	0.053*
C3'	0.3080 (2)	0.89318 (15)	0.40887 (13)	0.0432 (5)
H3'	0.3896	0.8679	0.4377	0.052*
C4	0.7030 (2)	0.59338 (17)	0.38321 (13)	0.0458 (5)
C4'	0.1937 (2)	0.83750 (16)	0.39470 (13)	0.0433 (5)
C5	0.5861 (2)	0.55008 (19)	0.33762 (15)	0.0545 (6)
H5	0.5061	0.5836	0.3283	0.065*
C5'	0.0740 (2)	0.87772 (17)	0.35111 (14)	0.0486 (5)
H5'	−0.0038	0.8417	0.3423	0.058*
C6	0.5852 (2)	0.45980 (19)	0.30610 (16)	0.0588 (7)
H6	0.5058	0.4342	0.2745	0.071*
C6'	0.0668 (2)	0.96912 (17)	0.32055 (15)	0.0530 (6)
H6'	−0.0146	0.9930	0.2901	0.064*
C7	0.6947 (2)	0.69072 (17)	0.41681 (13)	0.0464 (5)
C7'	0.1950 (2)	0.73673 (16)	0.42440 (13)	0.0426 (5)
C8	0.8122 (3)	0.83675 (19)	0.47275 (15)	0.0569 (6)
H8A	0.8988	0.8474	0.5103	0.068*
H8B	0.7455	0.8418	0.5015	0.068*
C8'	0.3254 (2)	0.59067 (16)	0.46412 (14)	0.0495 (6)
H8'A	0.2655	0.5777	0.4964	0.059*
H8'B	0.4158	0.5799	0.4969	0.059*
C9	0.7875 (2)	0.91368 (18)	0.41080 (17)	0.0528 (6)
C9'	0.2959 (2)	0.52156 (16)	0.39587 (14)	0.0458 (5)
C10	0.7937 (3)	1.0825 (2)	0.3943 (2)	0.0863 (10)
H10D	0.8540	1.1333	0.4180	0.130*
H10E	0.7036	1.1033	0.3878	0.130*
H10F	0.8055	1.0667	0.3434	0.130*
C10'	0.3005 (3)	0.3553 (2)	0.3677 (2)	0.0757 (9)
H10A	0.3653	0.3050	0.3839	0.114*
H10B	0.2997	0.3773	0.3156	0.114*
H10C	0.2138	0.3312	0.3666	0.114*
C11	0.5910 (4)	0.2707 (2)	0.2494 (2)	0.0936 (11)
H11D	0.5337	0.2608	0.2831	0.140*
H11E	0.6125	0.2098	0.2304	0.140*
H11F	0.5463	0.3103	0.2052	0.140*
C11'	0.0631 (3)	1.1560 (2)	0.25777 (19)	0.0801 (9)
H11A	−0.0002	1.1630	0.2880	0.120*
H11B	0.0270	1.1143	0.2134	0.120*
H11C	0.0814	1.2179	0.2389	0.120*
H2'	0.3781 (19)	0.7135 (17)	0.4293 (14)	0.049 (7)*
H2	0.8799 (19)	0.7210 (17)	0.4351 (15)	0.049 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0720 (12)	0.0635 (12)	0.0763 (13)	−0.0131 (10)	0.0076 (10)	−0.0211 (10)
O1'	0.0693 (11)	0.0466 (10)	0.0737 (12)	0.0043 (9)	0.0004 (9)	0.0127 (9)
O2	0.0815 (16)	0.0625 (14)	0.180 (3)	0.0145 (12)	−0.0038 (17)	−0.0290 (16)
O2'	0.0691 (13)	0.0446 (12)	0.163 (2)	−0.0081 (10)	0.0032 (14)	0.0035 (13)
O3	0.0439 (11)	0.0780 (15)	0.173 (3)	0.0028 (10)	0.0148 (13)	−0.0273 (16)
O3'	0.0447 (11)	0.0661 (14)	0.199 (3)	−0.0027 (10)	0.0301 (14)	0.0091 (15)
O4	0.0399 (8)	0.0660 (11)	0.0736 (11)	0.0104 (8)	0.0183 (8)	0.0060 (9)
O4'	0.0395 (8)	0.0518 (10)	0.0837 (12)	−0.0066 (7)	0.0210 (8)	0.0000 (9)
O5	0.0894 (14)	0.0647 (12)	0.0632 (12)	−0.0003 (11)	0.0215 (11)	−0.0005 (9)
O5'	0.0811 (13)	0.0605 (11)	0.0553 (11)	0.0090 (10)	0.0086 (10)	0.0041 (9)
O6	0.0583 (10)	0.0522 (11)	0.0941 (14)	−0.0040 (8)	0.0180 (10)	−0.0118 (10)
O6'	0.0528 (9)	0.0393 (9)	0.0741 (11)	0.0058 (7)	0.0132 (8)	0.0056 (8)
N1	0.0502 (12)	0.0539 (13)	0.0684 (13)	0.0031 (10)	0.0143 (10)	−0.0125 (10)
N1'	0.0493 (11)	0.0408 (11)	0.0788 (15)	−0.0036 (9)	0.0149 (10)	0.0020 (10)
N2	0.0395 (10)	0.0490 (12)	0.0679 (13)	0.0062 (9)	0.0140 (9)	−0.0024 (10)
N2'	0.0375 (9)	0.0394 (10)	0.0666 (13)	−0.0009 (8)	0.0168 (9)	0.0045 (9)
C1	0.0555 (14)	0.0541 (14)	0.0476 (13)	−0.0105 (11)	0.0112 (11)	−0.0020 (11)
C1'	0.0517 (13)	0.0397 (12)	0.0506 (13)	0.0065 (10)	0.0095 (10)	−0.0031 (10)
C2	0.0425 (11)	0.0498 (13)	0.0456 (12)	−0.0012 (10)	0.0137 (10)	0.0001 (10)
C2'	0.0402 (11)	0.0408 (12)	0.0546 (13)	−0.0012 (9)	0.0120 (10)	−0.0048 (10)
C3	0.0367 (10)	0.0510 (13)	0.0449 (12)	−0.0048 (9)	0.0110 (9)	0.0004 (10)
C3'	0.0352 (10)	0.0391 (11)	0.0519 (12)	0.0022 (9)	0.0066 (9)	−0.0029 (9)
C4	0.0374 (11)	0.0491 (13)	0.0504 (12)	−0.0006 (9)	0.0113 (9)	0.0100 (10)
C4'	0.0379 (11)	0.0395 (11)	0.0515 (12)	0.0002 (9)	0.0109 (9)	−0.0070 (10)
C5	0.0384 (12)	0.0568 (15)	0.0643 (15)	0.0003 (10)	0.0077 (11)	0.0135 (12)
C5'	0.0364 (11)	0.0449 (12)	0.0614 (14)	0.0004 (9)	0.0087 (10)	−0.0089 (10)
C6	0.0425 (12)	0.0654 (16)	0.0598 (15)	−0.0136 (11)	−0.0003 (11)	0.0053 (13)
C6'	0.0397 (11)	0.0505 (14)	0.0610 (14)	0.0076 (10)	0.0011 (10)	−0.0072 (11)
C7	0.0382 (11)	0.0536 (13)	0.0471 (12)	0.0056 (10)	0.0116 (9)	0.0109 (10)
C7'	0.0351 (10)	0.0414 (12)	0.0504 (12)	−0.0035 (9)	0.0107 (9)	−0.0060 (9)
C8	0.0499 (13)	0.0579 (15)	0.0592 (15)	0.0042 (11)	0.0090 (11)	−0.0081 (12)
C8'	0.0456 (12)	0.0432 (12)	0.0568 (14)	0.0009 (10)	0.0096 (10)	0.0064 (10)
C9	0.0385 (11)	0.0514 (14)	0.0693 (17)	0.0001 (10)	0.0162 (11)	−0.0076 (12)
C9'	0.0349 (10)	0.0453 (12)	0.0553 (14)	0.0019 (9)	0.0096 (10)	0.0067 (10)
C10	0.088 (2)	0.0523 (17)	0.130 (3)	−0.0070 (16)	0.050 (2)	0.0034 (18)
C10'	0.082 (2)	0.0484 (15)	0.103 (2)	−0.0009 (14)	0.0353 (18)	−0.0128 (15)
C11	0.092 (2)	0.074 (2)	0.101 (3)	−0.0303 (18)	0.005 (2)	−0.0312 (19)
C11'	0.091 (2)	0.0580 (17)	0.0742 (19)	0.0170 (16)	−0.0049 (17)	0.0139 (14)

Geometric parameters (Å, º) top

O1—C1	1.341 (3)	C3—H3	0.9300
O1—C11	1.424 (3)	C3'—C4'	1.385 (3)
O1'—C1'	1.340 (3)	C3'—H3'	0.9300
O1'—C11'	1.424 (3)	C4—C5	1.396 (3)
O2—N1	1.197 (3)	C4—C7	1.489 (3)
O2'—N1'	1.197 (3)	C4'—C5'	1.389 (3)
O3—N1	1.200 (3)	C4'—C7'	1.494 (3)
O3'—N1'	1.213 (3)	C5—C6	1.371 (4)
O4—C7	1.233 (3)	C5—H5	0.9300
O4'—C7'	1.231 (2)	C5'—C6'	1.374 (3)
O5—C9	1.192 (3)	C5'—H5'	0.9300
O5'—C9'	1.195 (3)	C6—H6	0.9300
O6—C9	1.332 (3)	C6'—H6'	0.9300
O6—C10	1.440 (4)	C8—C9	1.496 (4)
O6'—C9'	1.328 (3)	C8—H8A	0.9700
O6'—C10'	1.438 (3)	C8—H8B	0.9700
N1—C2	1.461 (3)	C8'—C9'	1.499 (3)
N1'—C2'	1.463 (3)	C8'—H8'A	0.9700
N2—C7	1.343 (3)	C8'—H8'B	0.9700
N2—C8	1.439 (3)	C10—H10D	0.9600
N2—H2	0.828 (16)	C10—H10E	0.9600
N2'—C7'	1.341 (3)	C10—H10F	0.9600
N2'—C8'	1.440 (3)	C10'—H10A	0.9600
N2'—H2'	0.833 (16)	C10'—H10B	0.9600
C1—C6	1.395 (4)	C10'—H10C	0.9600
C1—C2	1.407 (3)	C11—H11D	0.9600
C1'—C6'	1.394 (3)	C11—H11E	0.9600
C1'—C2'	1.407 (3)	C11—H11F	0.9600
C2—C3	1.378 (3)	C11'—H11A	0.9600
C2'—C3'	1.375 (3)	C11'—H11B	0.9600
C3—C4	1.389 (3)	C11'—H11C	0.9600

C1—O1—C11	118.7 (2)	C5'—C6'—H6'	119.7
C1'—O1'—C11'	118.7 (2)	C1'—C6'—H6'	119.7
C9—O6—C10	117.4 (2)	O4—C7—N2	121.9 (2)
C9'—O6'—C10'	117.7 (2)	O4—C7—C4	121.0 (2)
O2—N1—O3	121.1 (2)	N2—C7—C4	117.11 (19)
O2—N1—C2	120.6 (2)	O4'—C7'—N2'	122.3 (2)
O3—N1—C2	118.0 (2)	O4'—C7'—C4'	121.19 (19)
O2'—N1'—O3'	121.9 (2)	N2'—C7'—C4'	116.47 (18)
O2'—N1'—C2'	120.5 (2)	N2—C8—C9	113.5 (2)
O3'—N1'—C2'	117.2 (2)	N2—C8—H8A	108.9
C7—N2—C8	122.0 (2)	C9—C8—H8A	108.9
C7—N2—H2	122.2 (18)	N2—C8—H8B	108.9
C8—N2—H2	115.6 (18)	C9—C8—H8B	108.9
C7'—N2'—C8'	122.38 (19)	H8A—C8—H8B	107.7
C7'—N2'—H2'	122.0 (17)	N2'—C8'—C9'	113.4 (2)
C8'—N2'—H2'	115.0 (17)	N2'—C8'—H8'A	108.9
O1—C1—C6	124.5 (2)	C9'—C8'—H8'A	108.9
O1—C1—C2	118.1 (2)	N2'—C8'—H8'B	108.9
C6—C1—C2	117.4 (2)	C9'—C8'—H8'B	108.9
O1'—C1'—C6'	124.7 (2)	H8'A—C8'—H8'B	107.7
O1'—C1'—C2'	118.3 (2)	O5—C9—O6	125.0 (3)
C6'—C1'—C2'	116.9 (2)	O5—C9—C8	125.1 (2)
C3—C2—C1	121.5 (2)	O6—C9—C8	110.0 (2)
C3—C2—N1	117.0 (2)	O5'—C9'—O6'	125.3 (2)
C1—C2—N1	121.5 (2)	O5'—C9'—C8'	125.5 (2)
C3'—C2'—C1'	122.2 (2)	O6'—C9'—C8'	109.2 (2)
C3'—C2'—N1'	116.83 (19)	O6—C10—H10D	109.5
C1'—C2'—N1'	121.0 (2)	O6—C10—H10E	109.5
C2—C3—C4	120.8 (2)	H10D—C10—H10E	109.5
C2—C3—H3	119.6	O6—C10—H10F	109.5
C4—C3—H3	119.6	H10D—C10—H10F	109.5
C2'—C3'—C4'	120.1 (2)	H10E—C10—H10F	109.5
C2'—C3'—H3'	119.9	O6'—C10'—H10A	109.5
C4'—C3'—H3'	119.9	O6'—C10'—H10B	109.5
C3—C4—C5	117.5 (2)	H10A—C10'—H10B	109.5
C3—C4—C7	123.7 (2)	O6'—C10'—H10C	109.5
C5—C4—C7	118.8 (2)	H10A—C10'—H10C	109.5
C3'—C4'—C5'	118.1 (2)	H10B—C10'—H10C	109.5
C3'—C4'—C7'	122.56 (19)	O1—C11—H11D	109.5
C5'—C4'—C7'	119.31 (19)	O1—C11—H11E	109.5
C6—C5—C4	122.2 (2)	H11D—C11—H11E	109.5
C6—C5—H5	118.9	O1—C11—H11F	109.5
C4—C5—H5	118.9	H11D—C11—H11F	109.5
C6'—C5'—C4'	122.0 (2)	H11E—C11—H11F	109.5
C6'—C5'—H5'	119.0	O1'—C11'—H11A	109.5
C4'—C5'—H5'	119.0	O1'—C11'—H11B	109.5
C5—C6—C1	120.5 (2)	H11A—C11'—H11B	109.5
C5—C6—H6	119.7	O1'—C11'—H11C	109.5
C1—C6—H6	119.7	H11A—C11'—H11C	109.5
C5'—C6'—C1'	120.5 (2)	H11B—C11'—H11C	109.5

C11—O1—C1—C6	−3.9 (4)	C3'—C4'—C5'—C6'	1.6 (3)
C11—O1—C1—C2	177.3 (3)	C7'—C4'—C5'—C6'	−178.4 (2)
C11'—O1'—C1'—C6'	−1.0 (4)	C4—C5—C6—C1	2.2 (4)
C11'—O1'—C1'—C2'	177.4 (2)	O1—C1—C6—C5	179.4 (2)
O1—C1—C2—C3	178.6 (2)	C2—C1—C6—C5	−1.9 (4)
C6—C1—C2—C3	−0.2 (3)	C4'—C5'—C6'—C1'	−2.2 (4)
O1—C1—C2—N1	−2.8 (3)	O1'—C1'—C6'—C5'	179.2 (2)
C6—C1—C2—N1	178.3 (2)	C2'—C1'—C6'—C5'	0.9 (4)
O2—N1—C2—C3	159.7 (3)	C8—N2—C7—O4	−1.6 (4)
O3—N1—C2—C3	−13.9 (4)	C8—N2—C7—C4	178.6 (2)
O2—N1—C2—C1	−18.9 (4)	C3—C4—C7—O4	−160.1 (2)
O3—N1—C2—C1	167.5 (3)	C5—C4—C7—O4	18.0 (3)
O1'—C1'—C2'—C3'	−177.4 (2)	C3—C4—C7—N2	19.8 (3)
C6'—C1'—C2'—C3'	1.0 (3)	C5—C4—C7—N2	−162.1 (2)
O1'—C1'—C2'—N1'	2.4 (3)	C8'—N2'—C7'—O4'	3.0 (4)
C6'—C1'—C2'—N1'	−179.1 (2)	C8'—N2'—C7'—C4'	−176.1 (2)
O2'—N1'—C2'—C3'	−148.6 (3)	C3'—C4'—C7'—O4'	157.6 (2)
O3'—N1'—C2'—C3'	24.8 (4)	C5'—C4'—C7'—O4'	−22.4 (3)
O2'—N1'—C2'—C1'	31.6 (4)	C3'—C4'—C7'—N2'	−23.3 (3)
O3'—N1'—C2'—C1'	−155.0 (3)	C5'—C4'—C7'—N2'	156.7 (2)
C1—C2—C3—C4	2.1 (3)	C7—N2—C8—C9	−88.1 (3)
N1—C2—C3—C4	−176.5 (2)	C7'—N2'—C8'—C9'	87.3 (3)
C1'—C2'—C3'—C4'	−1.6 (4)	C10—O6—C9—O5	4.3 (4)
N1'—C2'—C3'—C4'	178.5 (2)	C10—O6—C9—C8	−175.3 (2)
C2—C3—C4—C5	−1.8 (3)	N2—C8—C9—O5	13.9 (4)
C2—C3—C4—C7	176.4 (2)	N2—C8—C9—O6	−166.5 (2)
C2'—C3'—C4'—C5'	0.3 (3)	C10'—O6'—C9'—O5'	−7.6 (4)
C2'—C3'—C4'—C7'	−179.7 (2)	C10'—O6'—C9'—C8'	172.9 (2)
C3—C4—C5—C6	−0.3 (4)	N2'—C8'—C9'—O5'	−10.9 (3)
C7—C4—C5—C6	−178.6 (2)	N2'—C8'—C9'—O6'	168.53 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4′ⁱ	0.83 (2)	2.26 (2)	3.069 (2)	167 (2)
N2′—H2′···O4	0.83 (2)	2.23 (2)	3.016 (2)	158 (2)

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₂N₂O₆
M_r	268.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	10.4378 (7), 13.9110 (9), 17.5420 (15)
β (°)	106.146 (8)
V (Å³)	2446.6 (3)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	1.03
Crystal size (mm)	0.28 × 0.26 × 0.24

Data collection
Diffractometer	Agilent Xcalibur Eos Gemini
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.760, 0.789
No. of measured, independent and observed [I > 2σ(I)] reflections	10600, 4251, 3287
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.155, 1.04
No. of reflections	4251
No. of parameters	356
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.31

Computer programs: CrysAlis PRO (Agilent, 2011), CrysAlis RED (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4'ⁱ	0.828 (16)	2.258 (17)	3.069 (2)	167 (2)
N2'—H2'···O4	0.833 (16)	2.229 (18)	3.016 (2)	158 (2)

Symmetry code: (i) x+1, y, z.

Acknowledgements

The authors thank Henan University of Traditional Chinese Medicine for supporting this study.

References

Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies Ltd, Yarnton, England. Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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