(Z)-2-(2-Amino­thia­zol-3-ium-4-yl)-2-[2-(tert-butoxy­carbon­yl)isopropoxyimino]acetate monohydrate

In the title compound, C₁₃H₁₉N₃O₅S·H₂O, the amino group is coplanar with the thia­zole ring. The dihedral angle between the thia­zole ring and the adjacent carboxyl­ate group is 86.9 (1)°. The tert-butyl group is disordered over two positions, with occupancies of 0.63 (4) and 0.37 (4). O—H...O and N—H...O hydrogen bonds link the mol­ecules into a two-dimensional network parallel to the (001) plane. The thia­zole rings of inversion-related mol­ecules are stacked with their centroids separated by a distance of 3.5387 (10) Å, indicating π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 223 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.041
• wR factor = 0.091
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.80 mm
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.35 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.07 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C4'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT301_ALERT_3_C Main Residue  Disorder .........................      15.00 Perc.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C1     -   C5     ...       1.53 Ang.
PLAT417_ALERT_2_C Short Inter D-H..H-D       H3A    ..  H6A     ..       2.11 Ang.

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         22

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 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
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

2-Aminothiazole compounds have been extensively studied because of their biological and industrial applications (Lynch et al., 1999; Toplak et al., 2003). A search of the Cambridge Structural Database (CSD, Version 5.28 of May 2007) reveals that there are 127 crystal structures containing the 2-aminothiazole moiety. The title compound is a very important intermediate of ceftazidime, which is among the most important cephalosporin antibiotics (Powers et al., 2001). Crystal structures of some cephalosporin intermediates which contain a 2-aminothiazole group have been reported (Yoshida et al., 1989; Laurent et al., 1981). The title compound can give a reactive intermediate by reaction with diethylenetriamine-N,N,N',N'',N''- pentaacetic acid (DTPA), further, which can be used to prepare a protein-chelator conjugate (Johnson, 1999). We report here the crystal structure of the title compound.

The thiazole ring is planar to within ±0.006 (1) Å. The amino group is coplanar with the thiazole ring, with atom N3 deviating from the thiazole plane by -0.021 (2) Å. The O1/N1/C1/C2/C5/C6/C10 plane is twisted away from the thiazole plane by 21.92 (8)°. The tert-butyl group is disordered over two positions, with occupancies of 0.63 (4) and 0.37 (4). The carboxylate plane (C1/C5/O4/O5) is nearly perpendicular to the thiazole ring (dihedral angle 86.9 (1)°).

The crystal structure is stabilized by intermolecular O—H···O and N—H···O hydrogen bonds (Table 1) involving the O atoms of the water molecules and carboxylate groups. These hydrogen bonds link the molecules into a two-dimensional network parallel to the (001) plane (Fig. 2). The thiazole rings of the inversion-related molecules at (x, y, z) and (1 - x, 1 - y, 1 - z) are stacked with their centroids separated by a distance of 3.5387 (10) Å, indicating π-π interactions.

Related literature

For synthesis, see: Furlenmeier et al. (1987); For general background, see: David (1999); Lynch et al. (1999); Rachel et al. (2001); Toplak et al. (2003). For related structures, see: Laurent et al. (1981); Yoshida et al. (1989).

S2. Experimental

The title compound was prepared according to the literature method (Furlenmeier et al., 1987). Crystals suitable for X-ray analysis were obtained by slow evaporation of a ethanol solution at room temperature (m.p. 471–473 K).

S3. Refinement

The tert-butyl group is disordered over two positions, with refined occupations 0.63 (4) and 0.37 (4). The C—C distances of the tert-butyl groups were restrained to 1.53 (1) Å, and the C—O and C···C distances involving disordered C-atoms were restrained to be equal. O– and N-bound H atoms were located from a difference Fourier map, and refined freely. C-bound H atoms were positioned geometrically (C—H = 0.94 or 0.97 Å) and refined using a riding model, with U_iso(H) = 1.2–1.5U_eq(C).

Computing details

Data collection: CrystalClear (Rigaku, 2001); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. Molecular structure of the title compound, showing 20% probability displacement ellipsoids and the atomic numbering. Only one disorder component is shown.
	Fig. 2. The crystal packing of the title compound, viewed approximately down the a axis. Dashed lines indicate intermolecular hydrogen bonds. Only one disorder component is shown.

(Z)-2-(2-Aminothiazol-3-ium-4-yl)-2-[2-(tert-butoxycarbonyl)- isopropoxyimino]acetate monohydrate

Crystal data

C13H19N3O5S·H2O	F(000) = 1472
Mr = 347.39	Dx = 1.304 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 31871 reflections
a = 12.7918 (17) Å	θ = 3.2–25.4°
b = 12.2489 (15) Å	µ = 0.21 mm^−1
c = 22.595 (3) Å	T = 223 K
V = 3540.2 (8) Å^3	Block, colourless
Z = 8	0.80 × 0.80 × 0.57 mm

Data collection

Rigaku Mercury diffractometer	3232 independent reflections
Radiation source: fine-focus sealed tube	3096 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 7.31 pixels mm^-1	θmax = 25.4°, θmin = 3.2°
ω scans	h = −15→15
Absorption correction: multi-scan (Jacobson, 1998)	k = −14→14
Tmin = 0.847, Tmax = 0.888	l = −27→26
31871 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.091	w = 1/[σ^2(Fo^2) + (0.0297P)^2 + 2.4239P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
3232 reflections	Δρmax = 0.20 e Å^−3
268 parameters	Δρmin = −0.28 e Å^−3
22 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0151 (7)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.46180 (4)	0.52078 (4)	0.40564 (2)	0.03825 (17)
O1	0.41053 (8)	0.12570 (9)	0.56784 (5)	0.0286 (3)
O2	0.47558 (11)	0.23610 (12)	0.66636 (6)	0.0455 (4)
O3	0.61809 (11)	0.13114 (11)	0.67241 (6)	0.0466 (4)
O4	0.24960 (11)	0.16967 (14)	0.45102 (7)	0.0585 (4)
O5	0.21461 (9)	0.25993 (12)	0.53369 (6)	0.0448 (4)
O6	0.29085 (12)	0.33757 (12)	0.63821 (7)	0.0406 (3)
N1	0.45637 (10)	0.20940 (11)	0.53363 (6)	0.0268 (3)
N2	0.53804 (11)	0.35198 (12)	0.45411 (6)	0.0276 (3)
N3	0.66501 (12)	0.46234 (15)	0.40943 (8)	0.0377 (4)
C1	0.38961 (12)	0.25548 (14)	0.49967 (7)	0.0263 (4)
C2	0.49082 (13)	0.07540 (14)	0.60427 (8)	0.0290 (4)
C3	0.52641 (13)	0.15890 (14)	0.65053 (8)	0.0297 (4)
C5	0.27385 (13)	0.22507 (14)	0.49359 (8)	0.0314 (4)
C6	0.43082 (12)	0.34460 (14)	0.46353 (7)	0.0271 (4)
C7	0.56742 (13)	0.43966 (14)	0.42388 (7)	0.0291 (4)
C8	0.37851 (14)	0.42879 (15)	0.43978 (8)	0.0360 (4)
H8	0.3055	0.4369	0.4415	0.043*
C9	0.58029 (15)	0.03195 (17)	0.56715 (9)	0.0412 (5)
H9A	0.5534	−0.0193	0.5382	0.062*
H9B	0.6303	−0.0048	0.5926	0.062*
H9C	0.6144	0.0921	0.5470	0.062*
C10	0.43324 (17)	−0.01592 (17)	0.63619 (10)	0.0488 (6)
H10A	0.3749	0.0144	0.6581	0.073*
H10B	0.4806	−0.0521	0.6633	0.073*
H10C	0.4075	−0.0683	0.6075	0.073*
C4	0.6558 (15)	0.1863 (12)	0.7277 (6)	0.043 (4)	0.37 (4)
C11	0.5784 (18)	0.1947 (19)	0.7785 (11)	0.065 (4)	0.37 (4)
H11A	0.5607	0.1221	0.7924	0.098*	0.37 (4)
H11B	0.5156	0.2314	0.7650	0.098*	0.37 (4)
H11C	0.6095	0.2361	0.8106	0.098*	0.37 (4)
C12	0.695 (2)	0.2988 (16)	0.7095 (11)	0.067 (5)	0.37 (4)
H12A	0.7427	0.2916	0.6764	0.100*	0.37 (4)
H12B	0.7307	0.3327	0.7425	0.100*	0.37 (4)
H12C	0.6360	0.3438	0.6978	0.100*	0.37 (4)
C13	0.7481 (17)	0.1146 (17)	0.7456 (11)	0.070 (4)	0.37 (4)
H13A	0.7230	0.0425	0.7561	0.106*	0.37 (4)
H13B	0.7834	0.1469	0.7793	0.106*	0.37 (4)
H13C	0.7966	0.1089	0.7127	0.106*	0.37 (4)
C4'	0.6727 (10)	0.1936 (8)	0.7204 (4)	0.043 (2)	0.63 (4)
C11'	0.6069 (13)	0.1748 (14)	0.7744 (6)	0.072 (3)	0.63 (4)
H11D	0.5892	0.0979	0.7772	0.108*	0.63 (4)
H11E	0.5433	0.2176	0.7715	0.108*	0.63 (4)
H11F	0.6456	0.1966	0.8093	0.108*	0.63 (4)
C12'	0.6832 (13)	0.3121 (8)	0.7044 (6)	0.063 (3)	0.63 (4)
H12D	0.7190	0.3186	0.6667	0.095*	0.63 (4)
H12E	0.7231	0.3495	0.7347	0.095*	0.63 (4)
H12F	0.6143	0.3447	0.7013	0.095*	0.63 (4)
C13'	0.7772 (12)	0.1372 (13)	0.7235 (9)	0.088 (4)	0.63 (4)
H13D	0.7667	0.0594	0.7289	0.132*	0.63 (4)
H13E	0.8168	0.1660	0.7566	0.132*	0.63 (4)
H13F	0.8154	0.1499	0.6871	0.132*	0.63 (4)
H6A	0.267 (2)	0.312 (2)	0.6048 (12)	0.069 (9)*
H6B	0.346 (2)	0.306 (2)	0.6449 (12)	0.069 (9)*
H2A	0.5873 (19)	0.3049 (19)	0.4660 (10)	0.054 (7)*
H3A	0.6783 (17)	0.5257 (19)	0.3913 (10)	0.046 (6)*
H3B	0.7138 (18)	0.4203 (19)	0.4232 (10)	0.052 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0322 (3)	0.0349 (3)	0.0477 (3)	0.00080 (19)	−0.0030 (2)	0.0154 (2)
O1	0.0212 (6)	0.0325 (6)	0.0321 (6)	−0.0040 (5)	−0.0045 (5)	0.0102 (5)
O2	0.0443 (8)	0.0477 (8)	0.0444 (8)	0.0147 (7)	−0.0090 (6)	−0.0099 (6)
O3	0.0436 (8)	0.0431 (8)	0.0530 (8)	0.0132 (6)	−0.0279 (7)	−0.0152 (7)
O4	0.0320 (7)	0.0720 (11)	0.0715 (10)	−0.0050 (7)	−0.0118 (8)	−0.0226 (9)
O5	0.0222 (6)	0.0611 (9)	0.0511 (8)	−0.0062 (6)	0.0044 (6)	−0.0019 (7)
O6	0.0370 (8)	0.0379 (8)	0.0470 (9)	0.0070 (6)	0.0045 (7)	0.0071 (7)
N1	0.0218 (7)	0.0297 (7)	0.0289 (7)	−0.0033 (6)	0.0001 (6)	0.0049 (6)
N2	0.0204 (7)	0.0297 (8)	0.0327 (8)	0.0001 (6)	−0.0001 (6)	0.0063 (6)
N3	0.0270 (8)	0.0373 (9)	0.0488 (10)	−0.0034 (7)	0.0050 (7)	0.0137 (8)
C1	0.0204 (8)	0.0294 (8)	0.0291 (8)	−0.0001 (7)	−0.0005 (7)	0.0012 (7)
C2	0.0249 (8)	0.0294 (9)	0.0328 (9)	0.0004 (7)	−0.0070 (7)	0.0055 (7)
C3	0.0292 (9)	0.0310 (9)	0.0289 (9)	0.0022 (7)	−0.0036 (7)	0.0055 (7)
C5	0.0233 (9)	0.0297 (9)	0.0410 (10)	−0.0020 (7)	−0.0066 (8)	0.0096 (8)
C6	0.0198 (8)	0.0334 (9)	0.0283 (9)	−0.0018 (7)	−0.0017 (7)	0.0026 (7)
C7	0.0281 (9)	0.0300 (9)	0.0293 (9)	−0.0014 (7)	0.0003 (7)	0.0016 (7)
C8	0.0224 (8)	0.0398 (10)	0.0458 (11)	0.0000 (8)	−0.0026 (8)	0.0105 (8)
C9	0.0357 (10)	0.0489 (12)	0.0390 (11)	0.0130 (9)	−0.0100 (9)	−0.0074 (9)
C10	0.0429 (11)	0.0425 (12)	0.0608 (14)	−0.0079 (10)	−0.0133 (10)	0.0226 (10)
C4	0.045 (6)	0.032 (6)	0.051 (8)	0.002 (4)	−0.024 (5)	−0.005 (4)
C11	0.089 (9)	0.070 (6)	0.036 (5)	0.016 (7)	−0.008 (6)	−0.004 (4)
C12	0.077 (9)	0.075 (10)	0.049 (7)	−0.004 (7)	−0.023 (6)	0.017 (6)
C13	0.069 (8)	0.075 (7)	0.068 (9)	0.027 (6)	−0.042 (6)	−0.025 (6)
C4'	0.048 (4)	0.044 (5)	0.037 (3)	0.000 (3)	−0.022 (3)	−0.007 (3)
C11'	0.090 (6)	0.091 (7)	0.036 (4)	−0.025 (5)	−0.021 (4)	0.008 (5)
C12'	0.079 (5)	0.047 (4)	0.064 (6)	−0.023 (4)	−0.035 (4)	0.000 (3)
C13'	0.069 (6)	0.093 (6)	0.102 (8)	0.028 (5)	−0.061 (5)	−0.039 (6)

Geometric parameters (Å, º)

S1—C7	1.7270 (18)	C9—H9C	0.97
S1—C8	1.7319 (18)	C10—H10A	0.97
O1—N1	1.4116 (17)	C10—H10B	0.97
O1—C2	1.4532 (19)	C10—H10C	0.97
O2—C3	1.202 (2)	C4—C13	1.526 (9)
O3—C3	1.317 (2)	C4—C12	1.523 (9)
O3—C4'	1.499 (5)	C4—C11	1.520 (9)
O3—C4	1.501 (7)	C11—H11A	0.97
O4—C5	1.217 (2)	C11—H11B	0.97
O5—C5	1.256 (2)	C11—H11C	0.97
O6—H6A	0.88 (3)	C12—H12A	0.97
O6—H6B	0.81 (3)	C12—H12B	0.97
N1—C1	1.279 (2)	C12—H12C	0.97
N2—C7	1.327 (2)	C13—H13A	0.97
N2—C6	1.391 (2)	C13—H13B	0.97
N2—H2A	0.90 (2)	C13—H13C	0.97
N3—C7	1.320 (2)	C4'—C12'	1.502 (7)
N3—H3A	0.89 (2)	C4'—C11'	1.500 (7)
N3—H3B	0.87 (2)	C4'—C13'	1.507 (7)
C1—C6	1.462 (2)	C11'—H11D	0.97
C1—C5	1.533 (2)	C11'—H11E	0.97
C2—C9	1.516 (3)	C11'—H11F	0.97
C2—C10	1.521 (3)	C12'—H12D	0.97
C2—C3	1.532 (2)	C12'—H12E	0.97
C6—C8	1.341 (2)	C12'—H12F	0.97
C8—H8	0.94	C13'—H13D	0.97
C9—H9A	0.97	C13'—H13E	0.97
C9—H9B	0.97	C13'—H13F	0.97
C7—S1—C8	90.04 (8)	O3—C4—C13	102.1 (11)
N1—O1—C2	108.93 (11)	O3—C4—C12	106.7 (14)
C3—O3—C4'	123.6 (5)	C13—C4—C12	109.8 (7)
C3—O3—C4	118.9 (7)	O3—C4—C11	116.8 (16)
H6A—O6—H6B	107 (3)	C13—C4—C11	110.1 (7)
C1—N1—O1	111.81 (13)	C12—C4—C11	110.9 (7)
C7—N2—C6	114.24 (15)	C4—C11—H11A	109.5
C7—N2—H2A	118.4 (15)	C4—C11—H11B	109.5
C6—N2—H2A	127.3 (15)	H11A—C11—H11B	109.5
C7—N3—H3A	118.4 (14)	C4—C11—H11C	109.5
C7—N3—H3B	117.8 (15)	H11A—C11—H11C	109.5
H3A—N3—H3B	123 (2)	H11B—C11—H11C	109.5
N1—C1—C6	115.08 (14)	C4—C12—H12A	109.5
N1—C1—C5	126.26 (15)	C4—C12—H12B	109.5
C6—C1—C5	118.66 (14)	H12A—C12—H12B	109.5
O1—C2—C9	111.67 (14)	C4—C12—H12C	109.5
O1—C2—C10	103.77 (13)	H12A—C12—H12C	109.5
C9—C2—C10	111.70 (17)	H12B—C12—H12C	109.5
O1—C2—C3	108.27 (13)	C4—C13—H13A	109.5
C9—C2—C3	112.81 (15)	C4—C13—H13B	109.5
C10—C2—C3	108.15 (15)	H13A—C13—H13B	109.5
O2—C3—O3	124.96 (17)	C4—C13—H13C	109.5
O2—C3—C2	124.58 (16)	H13A—C13—H13C	109.5
O3—C3—C2	110.39 (15)	H13B—C13—H13C	109.5
O4—C5—O5	127.28 (16)	O3—C4'—C12'	111.2 (7)
O4—C5—C1	116.90 (16)	O3—C4'—C11'	104.4 (10)
O5—C5—C1	115.81 (15)	C12'—C4'—C11'	113.3 (5)
C8—C6—N2	112.38 (15)	O3—C4'—C13'	102.3 (7)
C8—C6—C1	128.16 (15)	C12'—C4'—C13'	112.0 (6)
N2—C6—C1	119.32 (15)	C11'—C4'—C13'	112.9 (5)
N3—C7—N2	124.44 (17)	C4'—C11'—H11D	109.5
N3—C7—S1	124.03 (14)	C4'—C11'—H11E	109.5
N2—C7—S1	111.53 (12)	H11D—C11'—H11E	109.5
C6—C8—S1	111.81 (13)	C4'—C11'—H11F	109.5
C6—C8—H8	124.1	H11D—C11'—H11F	109.5
S1—C8—H8	124.1	H11E—C11'—H11F	109.5
C2—C9—H9A	109.5	C4'—C12'—H12D	109.5
C2—C9—H9B	109.5	C4'—C12'—H12E	109.5
H9A—C9—H9B	109.5	H12D—C12'—H12E	109.5
C2—C9—H9C	109.5	C4'—C12'—H12F	109.5
H9A—C9—H9C	109.5	H12D—C12'—H12F	109.5
H9B—C9—H9C	109.5	H12E—C12'—H12F	109.5
C2—C10—H10A	109.5	C4'—C13'—H13D	109.5
C2—C10—H10B	109.5	C4'—C13'—H13E	109.5
H10A—C10—H10B	109.5	H13D—C13'—H13E	109.5
C2—C10—H10C	109.5	C4'—C13'—H13F	109.5
H10A—C10—H10C	109.5	H13D—C13'—H13F	109.5
H10B—C10—H10C	109.5	H13E—C13'—H13F	109.5
C2—O1—N1—C1	178.74 (14)	C7—N2—C6—C8	0.0 (2)
O1—N1—C1—C6	178.92 (13)	C7—N2—C6—C1	−175.93 (15)
O1—N1—C1—C5	−1.7 (2)	N1—C1—C6—C8	−155.94 (19)
N1—O1—C2—C9	−56.78 (17)	C5—C1—C6—C8	24.6 (3)
N1—O1—C2—C10	−177.25 (14)	N1—C1—C6—N2	19.3 (2)
N1—O1—C2—C3	68.00 (16)	C5—C1—C6—N2	−160.16 (16)
C4'—O3—C3—O2	−0.5 (7)	C6—N2—C7—N3	−179.26 (17)
C4—O3—C3—O2	11.0 (10)	C6—N2—C7—S1	0.70 (19)
C4'—O3—C3—C2	−177.5 (7)	C8—S1—C7—N3	179.04 (17)
C4—O3—C3—C2	−166.0 (9)	C8—S1—C7—N2	−0.91 (14)
O1—C2—C3—O2	21.9 (2)	N2—C6—C8—S1	−0.7 (2)
C9—C2—C3—O2	146.04 (18)	C1—C6—C8—S1	174.79 (15)
C10—C2—C3—O2	−89.9 (2)	C7—S1—C8—C6	0.92 (15)
O1—C2—C3—O3	−161.07 (14)	C3—O3—C4—C13	167.3 (10)
C9—C2—C3—O3	−37.0 (2)	C3—O3—C4—C12	−77.5 (12)
C10—C2—C3—O3	87.09 (18)	C3—O3—C4—C11	47.2 (13)
N1—C1—C5—O4	−100.4 (2)	C3—O3—C4'—C12'	−53.7 (12)
C6—C1—C5—O4	78.9 (2)	C3—O3—C4'—C11'	68.8 (10)
N1—C1—C5—O5	79.1 (2)	C3—O3—C4'—C13'	−173.4 (9)
C6—C1—C5—O5	−101.53 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O5	0.88 (3)	1.85 (3)	2.726 (2)	179 (3)
O6—H6B···O2	0.81 (3)	1.93 (3)	2.745 (2)	176 (3)
N2—H2A···O5^i	0.90 (2)	1.81 (2)	2.656 (2)	156 (2)
N3—H3A···O6^ii	0.89 (2)	1.85 (2)	2.736 (2)	174 (2)
N3—H3B···O5^i	0.87 (2)	2.41 (2)	3.077 (2)	134 (2)
N3—H3B···O1^i	0.87 (2)	2.59 (2)	3.360 (2)	149 (2)

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