Methyl 2-(4-meth-oxy-3-nitro-benzamido)-acetate.

The title compound, C(11)H(12)N(2)O(6), crystallizes with two independent mol-ecules 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 mol-ecule and 23.4 (3)° in the other. In the crystal, the two independent mol-ecules 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 = 268.23

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.155

S = 1.04

4251 reflections

356 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.31 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029522/is5151sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029522/is5151Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029522/is5151Isup3.cml

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

C11H12N2O6	F(000) = 1120
Mr = 268.23	Dx = 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 = 1.04 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

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

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(Fo2) + (0.073P)2 + 0.8379P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.004
4251 reflections	Δρmax = 0.50 e Å−3
356 parameters	Δρmin = −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)

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
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)*

	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)

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)

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)

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) .