N2-(2-Nitrophenyl­sulfon­yl)-N5-n-propylglutamine

Xiao, Y.-J.; Wang, J.-G.; Li, Z.-M.; Song, H.-B.

doi:10.1107/S1600536805030114

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N²-(2-Nitrophenylsulfonyl)-N⁵-n-propylglutamine

Y.-J. Xiao, J.-G. Wang, Z.-M. Li and H.-B. Song

The title compound, C₁₄H₁₉N₃O₇S, is a potent new herbicide. X-ray analysis reveals that the nitro group is twisted away from the benzene ring and the glutamine residue adopts a folded conformation. The crystal packing is stabilized by intermolecular N—H

O and O—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030114/ci6653sup1.cif Contains datablocks 050802b, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030114/ci6653Isup2.hkl Contains datablock I

CCDC reference: 287528

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.003 Å
R factor = 0.029
wR factor = 0.068
Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.44 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C4      ..       6.57 su
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.06

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.36
           From the CIF: _reflns_number_total               3293
           Count of symmetry unique reflns         1863
           Completeness (_total/calc)            176.76%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1430
           Fraction of Friedel pairs measured     0.768
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Based on the reported 2.8 Å high-resolution crystal structure of yeast AHAS (acetohydroxyacid synthase) complex (Pang et al., 2003), we obtained 300 molecules with low binding energy toward AHAS from MDL/ACD three-dimensional database searching, using the program DOCK 4.0 (Wang et al., 2005). These potential structures provide information for further design of new targeted AHAS herbicidal molecules. According to the structural information and bioactivity data of 5-N-substituted-2-(substituted benzenesulfonyl)glutamine, a series of these derivatives have been designed and synthesized. The X-ray crystal structure determination of the title compound, (I), was undertaken to investigate the relationship between structure and herbicidal activity.

The bond lengths and angles in (I) show normal values (Table 1). The O3—S1—O4 angle [120.39 (10)°] deviates significantly from the ideal tetrahedral value. The O—N—C—C torsion angles indicate that the nitro group is twisted away from the plane of the benzene ring (Fig. 1). In the glutamine residue, the ψ¹ (N2—C7—C8—O5), ψ² (N2—C7—C8—O6), χ¹ (N2—C7—C9—C10) and χ² (C7—C9—C10—C11) torsion angles are 11.2 (3), −169.67 (16), 66.3 (2) and −62.7 (2)°, respectively; the two planar groups in the residue, C7/C8/O5/O6 and C10/C11/O7/N3, form a dihedral angle of 32.0 (1)°.

The molecular structure is stabilized by intramolecular N—H···O hydrogen bonds (Table 2). The crystal structure involves intermolecular O—H···O and N—H···O hydrogen bonds, which link the molecules into a layer parallel to the ab plane (Fig. 2).

Experimental top

Compound (I) was prepared according to the procedure of Srikanth et al. (2002). Colourless single crystals suitable for X-ray diffraction analysis were obtained by recrystallization from ethanol and water (8:2 v/v).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The structure of (I). Displacement ellipsoids are drawn at the 30% probability level. Dashed lines indicate intramolecular hydrogen bonds.
	Fig. 2. The crystal packing of (I), viewed along the c axis. Dashed lines indicate hydrogen bonds.

5-N-n-propyl-2-(2'-nitro benzenesulfonyl)glutamine top

Crystal data top

C₁₄H₁₉N₃O₇S	F(000) = 392
M_r = 373.38	D_x = 1.463 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2760 reflections
a = 6.9215 (13) Å	θ = 2.9–26.2°
b = 7.7539 (16) Å	µ = 0.23 mm⁻¹
c = 15.797 (3) Å	T = 294 K
β = 91.858 (3)°	Prism, colourless
V = 847.3 (3) Å³	0.26 × 0.20 × 0.18 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	3293 independent reflections
Radiation source: fine-focus sealed tube	2977 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 26.4°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→5
T_min = 0.935, T_max = 0.959	k = −9→9
4767 measured reflections	l = −16→19

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)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.069	w = 1/[σ²(F_o²) + (0.029P)² + 0.1123P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
3293 reflections	Δρ_max = 0.14 e Å⁻³
239 parameters	Δρ_min = −0.17 e Å⁻³
19 restraints	Absolute structure: Flack (1983), 1439 Friedel Pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (6)

Crystal data top

C₁₄H₁₉N₃O₇S	V = 847.3 (3) Å³
M_r = 373.38	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 6.9215 (13) Å	µ = 0.23 mm⁻¹
b = 7.7539 (16) Å	T = 294 K
c = 15.797 (3) Å	0.26 × 0.20 × 0.18 mm
β = 91.858 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3293 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2977 reflections with I > 2σ(I)
T_min = 0.935, T_max = 0.959	R_int = 0.018
4767 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.069	Δρ_max = 0.14 e Å⁻³
S = 1.06	Δρ_min = −0.17 e Å⁻³
3293 reflections	Absolute structure: Flack (1983), 1439 Friedel Pairs
239 parameters	Absolute structure parameter: 0.00 (6)
19 restraints

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
S1	0.18001 (6)	0.51289 (6)	0.68311 (3)	0.03880 (12)
O1	−0.3398 (3)	0.6233 (3)	0.55017 (11)	0.0717 (5)
O2	−0.2398 (2)	0.6410 (2)	0.68034 (10)	0.0639 (5)
O3	0.1560 (2)	0.6676 (2)	0.63517 (9)	0.0549 (4)
O4	0.36377 (19)	0.4296 (2)	0.68935 (9)	0.0573 (4)
O5	−0.1683 (2)	0.5317 (2)	0.88503 (9)	0.0569 (4)
O6	−0.0053 (2)	0.3581 (2)	0.97427 (10)	0.0565 (4)
H6	−0.096 (4)	0.366 (4)	1.0065 (18)	0.077 (9)*
O7	0.2637 (2)	0.8944 (2)	0.91572 (10)	0.0593 (4)
N1	−0.2546 (2)	0.5661 (2)	0.61264 (12)	0.0460 (4)
N2	0.1168 (2)	0.5534 (2)	0.77864 (9)	0.0353 (4)
H2A	0.015 (3)	0.605 (3)	0.7804 (12)	0.032 (5)*
N3	0.4870 (2)	0.7868 (2)	0.83201 (11)	0.0439 (4)
H3A	0.552 (3)	0.699 (3)	0.8216 (12)	0.036 (6)*
C1	−0.1706 (3)	0.3927 (3)	0.60670 (11)	0.0390 (4)
C2	−0.2864 (4)	0.2677 (3)	0.56901 (14)	0.0525 (6)
H2	−0.4089	0.2961	0.5474	0.063*
C3	−0.2199 (4)	0.1008 (3)	0.56359 (15)	0.0624 (7)
H3	−0.2987	0.0152	0.5399	0.075*
C4	−0.0358 (4)	0.0613 (3)	0.59349 (14)	0.0644 (7)
H4	0.0098	−0.0512	0.5893	0.077*
C5	0.0824 (3)	0.1880 (3)	0.62986 (13)	0.0506 (6)
H5	0.2072	0.1599	0.6487	0.061*
C6	0.0162 (3)	0.3560 (2)	0.63831 (11)	0.0364 (4)
C7	0.1436 (2)	0.4253 (3)	0.84651 (11)	0.0338 (4)
H7	0.1355	0.3105	0.8207	0.041*
C8	−0.0298 (3)	0.4461 (3)	0.90434 (12)	0.0389 (4)
C9	0.3402 (3)	0.4401 (3)	0.89322 (12)	0.0380 (4)
H9A	0.3554	0.3423	0.9312	0.046*
H9B	0.4406	0.4322	0.8520	0.046*
C10	0.3718 (3)	0.6050 (3)	0.94448 (12)	0.0413 (5)
H10A	0.2728	0.6109	0.9864	0.050*
H10B	0.4954	0.5958	0.9749	0.050*
C11	0.3693 (3)	0.7717 (3)	0.89619 (12)	0.0382 (4)
C12	0.4937 (3)	0.9371 (3)	0.77660 (13)	0.0528 (6)
H12A	0.3679	0.9922	0.7743	0.063*
H12B	0.5221	0.8996	0.7198	0.063*
C13	0.6454 (4)	1.0679 (3)	0.80635 (16)	0.0644 (7)
H13A	0.6504	1.1601	0.7650	0.077*
H13B	0.6061	1.1178	0.8594	0.077*
C14	0.8432 (4)	0.9928 (4)	0.81882 (18)	0.0734 (7)
H14A	0.8842	0.9444	0.7664	0.110*
H14B	0.8407	0.9041	0.8612	0.110*
H14C	0.9319	1.0817	0.8369	0.110*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0325 (2)	0.0509 (3)	0.0333 (2)	−0.0019 (2)	0.00619 (17)	0.0019 (2)
O1	0.0708 (11)	0.0736 (12)	0.0696 (11)	0.0181 (10)	−0.0181 (9)	0.0120 (10)
O2	0.0600 (10)	0.0616 (11)	0.0692 (11)	0.0183 (8)	−0.0100 (8)	−0.0251 (10)
O3	0.0642 (10)	0.0564 (10)	0.0443 (8)	−0.0143 (8)	0.0036 (7)	0.0116 (7)
O4	0.0339 (7)	0.0891 (12)	0.0495 (8)	0.0076 (8)	0.0101 (6)	−0.0030 (8)
O5	0.0358 (7)	0.0788 (12)	0.0567 (8)	0.0096 (8)	0.0123 (6)	0.0106 (9)
O6	0.0477 (9)	0.0739 (12)	0.0487 (9)	−0.0050 (8)	0.0153 (7)	0.0179 (8)
O7	0.0567 (9)	0.0686 (11)	0.0540 (9)	0.0197 (8)	0.0215 (7)	−0.0025 (8)
N1	0.0363 (9)	0.0493 (12)	0.0520 (11)	0.0046 (8)	−0.0026 (8)	0.0009 (9)
N2	0.0292 (8)	0.0433 (10)	0.0335 (8)	0.0030 (7)	0.0019 (6)	0.0007 (7)
N3	0.0359 (9)	0.0445 (11)	0.0523 (10)	0.0040 (8)	0.0160 (8)	0.0008 (9)
C1	0.0430 (11)	0.0423 (11)	0.0317 (9)	−0.0001 (9)	0.0020 (8)	0.0002 (8)
C2	0.0563 (14)	0.0604 (15)	0.0405 (11)	−0.0094 (11)	−0.0025 (10)	−0.0070 (11)
C3	0.0868 (19)	0.0510 (14)	0.0493 (13)	−0.0098 (13)	0.0000 (13)	−0.0117 (11)
C4	0.106 (2)	0.0380 (13)	0.0500 (13)	0.0072 (12)	0.0117 (13)	−0.0061 (10)
C5	0.0653 (15)	0.0486 (13)	0.0380 (11)	0.0155 (11)	0.0041 (10)	−0.0011 (10)
C6	0.0427 (11)	0.0405 (11)	0.0264 (9)	0.0036 (9)	0.0054 (7)	−0.0019 (8)
C7	0.0328 (10)	0.0338 (10)	0.0350 (9)	−0.0027 (8)	0.0046 (7)	−0.0004 (8)
C8	0.0338 (10)	0.0438 (11)	0.0393 (10)	−0.0116 (9)	0.0052 (8)	−0.0031 (9)
C9	0.0303 (9)	0.0457 (11)	0.0384 (10)	0.0060 (8)	0.0050 (8)	0.0038 (9)
C10	0.0311 (10)	0.0597 (13)	0.0332 (10)	−0.0027 (9)	0.0036 (8)	−0.0008 (9)
C11	0.0273 (9)	0.0512 (12)	0.0362 (10)	−0.0017 (8)	0.0002 (7)	−0.0104 (9)
C12	0.0523 (13)	0.0627 (14)	0.0438 (11)	0.0145 (12)	0.0087 (9)	0.0053 (11)
C13	0.103 (2)	0.0396 (13)	0.0520 (13)	0.0030 (13)	0.0188 (13)	0.0066 (10)
C14	0.0671 (16)	0.0681 (18)	0.0850 (17)	−0.0279 (14)	0.0025 (13)	0.0056 (15)

Geometric parameters (Å, º) top

S1—O3	1.4255 (16)	C4—C5	1.391 (3)
S1—O4	1.4269 (15)	C4—H4	0.93
S1—N2	1.6157 (16)	C5—C6	1.389 (3)
S1—C6	1.793 (2)	C5—H5	0.93
O1—N1	1.216 (2)	C7—C9	1.531 (3)
O2—N1	1.218 (2)	C7—C8	1.540 (2)
O5—C8	1.198 (2)	C7—H7	0.98
O6—C8	1.305 (2)	C9—C10	1.526 (3)
O6—H6	0.82 (3)	C9—H9A	0.97
O7—C11	1.245 (2)	C9—H9B	0.97
N1—C1	1.470 (3)	C10—C11	1.501 (3)
N2—C7	1.469 (2)	C10—H10A	0.97
N2—H2A	0.81 (2)	C10—H10B	0.97
N3—C11	1.326 (2)	C12—C13	1.523 (4)
N3—C12	1.459 (3)	C12—H12A	0.97
N3—H3A	0.83 (2)	C12—H12B	0.97
C1—C2	1.380 (3)	C13—C14	1.495 (4)
C1—C6	1.400 (3)	C13—H13A	0.97
C2—C3	1.377 (4)	C13—H13B	0.97
C2—H2	0.93	C14—H14A	0.96
C3—C4	1.379 (4)	C14—H14B	0.96
C3—H3	0.93	C14—H14C	0.96

O3—S1—O4	120.39 (10)	C9—C7—H7	107.9
O3—S1—N2	107.58 (9)	C8—C7—H7	107.9
O4—S1—N2	106.92 (8)	O5—C8—O6	125.90 (18)
O3—S1—C6	107.45 (9)	O5—C8—C7	122.67 (17)
O4—S1—C6	105.73 (10)	O6—C8—C7	111.43 (18)
N2—S1—C6	108.29 (8)	C10—C9—C7	115.36 (16)
C8—O6—H6	114 (2)	C10—C9—H9A	108.4
O1—N1—O2	124.29 (18)	C7—C9—H9A	108.4
O1—N1—C1	117.65 (18)	C10—C9—H9B	108.4
O2—N1—C1	118.02 (17)	C7—C9—H9B	108.4
C7—N2—S1	121.24 (13)	H9A—C9—H9B	107.5
C7—N2—H2A	113.5 (14)	C11—C10—C9	116.94 (14)
S1—N2—H2A	112.9 (13)	C11—C10—H10A	108.1
C11—N3—C12	124.19 (18)	C9—C10—H10A	108.1
C11—N3—H3A	115.3 (14)	C11—C10—H10B	108.1
C12—N3—H3A	120.3 (14)	C9—C10—H10B	108.1
C2—C1—C6	121.9 (2)	H10A—C10—H10B	107.3
C2—C1—N1	116.37 (18)	O7—C11—N3	120.13 (19)
C6—C1—N1	121.74 (17)	O7—C11—C10	121.98 (17)
C3—C2—C1	119.7 (2)	N3—C11—C10	117.88 (17)
C3—C2—H2	120.1	N3—C12—C13	112.45 (18)
C1—C2—H2	120.1	N3—C12—H12A	109.1
C2—C3—C4	119.7 (2)	C13—C12—H12A	109.1
C2—C3—H3	120.2	N3—C12—H12B	109.1
C4—C3—H3	120.2	C13—C12—H12B	109.1
C3—C4—C5	120.6 (2)	H12A—C12—H12B	107.8
C3—C4—H4	119.7	C14—C13—C12	113.6 (2)
C5—C4—H4	119.7	C14—C13—H13A	108.8
C6—C5—C4	120.7 (2)	C12—C13—H13A	108.8
C6—C5—H5	119.6	C14—C13—H13B	108.8
C4—C5—H5	119.6	C12—C13—H13B	108.8
C5—C6—C1	117.39 (19)	H13A—C13—H13B	107.7
C5—C6—S1	117.90 (16)	C13—C14—H14A	109.5
C1—C6—S1	124.61 (15)	C13—C14—H14B	109.5
N2—C7—C9	112.97 (15)	H14A—C14—H14B	109.5
N2—C7—C8	106.26 (15)	C13—C14—H14C	109.5
C9—C7—C8	113.82 (14)	H14A—C14—H14C	109.5
N2—C7—H7	107.9	H14B—C14—H14C	109.5

O3—S1—N2—C7	−173.61 (13)	N2—S1—C6—C5	−105.60 (16)
O4—S1—N2—C7	−42.98 (16)	O3—S1—C6—C1	−37.70 (17)
C6—S1—N2—C7	70.54 (15)	O4—S1—C6—C1	−167.46 (15)
O1—N1—C1—C2	−45.2 (3)	N2—S1—C6—C1	78.24 (17)
O2—N1—C1—C2	132.6 (2)	S1—N2—C7—C9	89.94 (17)
O1—N1—C1—C6	135.4 (2)	S1—N2—C7—C8	−144.58 (13)
O2—N1—C1—C6	−46.8 (3)	N2—C7—C8—O5	11.2 (3)
C6—C1—C2—C3	1.5 (3)	C9—C7—C8—O5	136.1 (2)
N1—C1—C2—C3	−177.9 (2)	N2—C7—C8—O6	−169.67 (16)
C1—C2—C3—C4	−2.0 (4)	C9—C7—C8—O6	−44.7 (2)
C2—C3—C4—C5	0.7 (4)	N2—C7—C9—C10	66.3 (2)
C3—C4—C5—C6	1.3 (3)	C8—C7—C9—C10	−55.0 (2)
C4—C5—C6—C1	−1.8 (3)	C7—C9—C10—C11	−62.7 (2)
C4—C5—C6—S1	−178.25 (16)	C12—N3—C11—O7	−4.5 (3)
C2—C1—C6—C5	0.5 (3)	C12—N3—C11—C10	176.71 (19)
N1—C1—C6—C5	179.84 (18)	C9—C10—C11—O7	127.2 (2)
C2—C1—C6—S1	176.64 (15)	C9—C10—C11—N3	−54.1 (2)
N1—C1—C6—S1	−4.0 (3)	C11—N3—C12—C13	93.2 (2)
O3—S1—C6—C5	138.46 (15)	N3—C12—C13—C14	54.2 (3)
O4—S1—C6—C5	8.71 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O7ⁱ	0.82 (3)	1.73 (3)	2.549 (2)	172 (3)
N2—H2A···O5	0.81 (2)	2.192 (19)	2.639 (2)	115 (2)
N2—H2A···O2	0.81 (2)	2.347 (19)	2.952 (2)	132 (2)
N3—H3A···O5ⁱⁱ	0.83 (2)	2.52 (2)	3.190 (2)	139 (2)

Symmetry codes: (i) −x, y−1/2, −z+2; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₉N₃O₇S
M_r	373.38
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	294
a, b, c (Å)	6.9215 (13), 7.7539 (16), 15.797 (3)
β (°)	91.858 (3)
V (Å³)	847.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.26 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.935, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	4767, 3293, 2977
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.069, 1.06
No. of reflections	3293
No. of parameters	239
No. of restraints	19
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.17
Absolute structure	Flack (1983), 1439 Friedel Pairs
Absolute structure parameter	0.00 (6)

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.

Selected geometric parameters (Å, º) top

S1—N2	1.6157 (16)	N1—C1	1.470 (3)
S1—C6	1.793 (2)	N2—C7	1.469 (2)
O5—C8	1.198 (2)	N3—C11	1.326 (2)
O6—C8	1.305 (2)	N3—C12	1.459 (3)
O7—C11	1.245 (2)

O5—C8—O6	125.90 (18)	O7—C11—C10	121.98 (17)
O6—C8—C7	111.43 (18)	N3—C12—C13	112.45 (18)

O1—N1—C1—C2	−45.2 (3)	C12—N3—C11—O7	−4.5 (3)
O2—N1—C1—C2	132.6 (2)	C9—C10—C11—O7	127.2 (2)
O1—N1—C1—C6	135.4 (2)	C9—C10—C11—N3	−54.1 (2)
O2—N1—C1—C6	−46.8 (3)	N3—C12—C13—C14	54.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O7ⁱ	0.82 (3)	1.73 (3)	2.549 (2)	172 (3)
N2—H2A···O5	0.81 (2)	2.192 (19)	2.639 (2)	115 (2)
N2—H2A···O2	0.81 (2)	2.347 (19)	2.952 (2)	132 (2)
N3—H3A···O5ⁱⁱ	0.83 (2)	2.52 (2)	3.190 (2)	139 (2)

Symmetry codes: (i) −x, y−1/2, −z+2; (ii) x+1, y, z.

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