rac-(4R,17S,18R,26R)-Ethyl 4'-methoxy-carbonyl-5''-(4-methoxy-phen-yl)-1'-methyl-2,3''-dioxo-2'',3''-dihydro-indoline-3-spiro-2'-pyrrolidine-3'-spiro-2''-thia-zolo[3,2-a]pyrimidine-6''-carboxyl-ate.

In the title compound, C(30)H(30)N(4)O(7)S, the two spiro junctions link a planar 2-oxindole ring [with a mean deviation from the plane of 0.0319 (3) Å, a pyrrolidine ring in an envelope conformation and a thia-zolo[3,2-a]pyrimidine system. Two mol-ecules are connected into a dimer by two N-H⋯O hydrogen bonds, forming an R(2) (2)(8) graph-set motif. The title compound has four stereogenic centers and appears as a racemic mixture of one single diastereoisomer (RSRR/SRSS).

Related literature

For related literature on spiro compounds, see: Caramella & Grunanger (1984 ▶); James et al. (1991 ▶); Kobayashi et al. (1991 ▶). For structural discussion, see: Cremer & Pople (1975 ▶); Etter (1990 ▶); Bernstein et al. (1994 ▶).

Experimental

Crystal data

C30H30N4O7S

M = 590.64

Triclinic,

a = 9.944 (2) Å

b = 11.389 (2) Å

c = 13.417 (3) Å

α = 98.06 (3)°

β = 107.36 (3)°

γ = 101.00 (3)°

V = 1391.8 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.17 mm−1

T = 113 (2) K

0.20 × 0.18 × 0.08 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2001 ▶) T min = 0.956, T max = 0.977

10220 measured reflections

4881 independent reflections

3700 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.098

S = 1.06

4881 reflections

384 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrystalClear (Rigaku, 2001 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900261X/dn2427sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900261X/dn2427Isup2.hkl

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

C30H30N4O7S	Z = 2
Mr = 590.64	F(000) = 620
Triclinic, P1	Dx = 1.409 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.944 (2) Å	Cell parameters from 4258 reflections
b = 11.389 (2) Å	θ = 1.8–27.9°
c = 13.417 (3) Å	µ = 0.17 mm−1
α = 98.06 (3)°	T = 113 K
β = 107.36 (3)°	Block, colourless
γ = 101.00 (3)°	0.20 × 0.18 × 0.08 mm
V = 1391.8 (6) Å3

Rigaku Saturn diffractometer	4881 independent reflections
Radiation source: rotating anode	3700 reflections with I > 2σ(I)
confocal	Rint = 0.029
ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2001)	h = −11→11
Tmin = 0.956, Tmax = 0.977	k = −13→10
10220 measured reflections	l = −15→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0589P)2] where P = (Fo2 + 2Fc2)/3
4881 reflections	(Δ/σ)max < 0.001
384 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
S1	0.04156 (5)	0.35302 (4)	0.42322 (3)	0.02231 (13)
O1	0.32486 (14)	−0.13252 (12)	0.32935 (11)	0.0354 (3)
O2	0.26663 (13)	−0.05624 (11)	0.18117 (10)	0.0281 (3)
O3	−0.42217 (12)	−0.30677 (11)	0.05644 (10)	0.0316 (3)
O4	−0.02319 (12)	0.24227 (10)	0.12268 (9)	0.0236 (3)
O5	−0.11369 (12)	0.48453 (10)	0.08582 (8)	0.0218 (3)
O6	−0.27264 (14)	0.17208 (12)	0.27772 (13)	0.0429 (4)
O7	−0.39268 (13)	0.31585 (11)	0.30007 (10)	0.0328 (3)
N1	0.16597 (15)	0.16869 (13)	0.46129 (11)	0.0241 (3)
N2	0.07144 (14)	0.18849 (12)	0.28126 (10)	0.0174 (3)
N3	0.13510 (14)	0.52812 (12)	0.12989 (11)	0.0208 (3)
H3	0.1406	0.5309	0.0674	0.025*
N4	−0.02410 (14)	0.56993 (12)	0.32782 (10)	0.0182 (3)
C1	0.3131 (2)	0.02959 (19)	0.51724 (15)	0.0344 (5)
H1A	0.3593	−0.0288	0.4913	0.052*
H1B	0.2512	−0.0083	0.5526	0.052*
H1C	0.3858	0.0978	0.5667	0.052*
C2	0.22450 (18)	0.07314 (16)	0.42587 (14)	0.0229 (4)
C3	0.20286 (17)	0.03199 (15)	0.32123 (14)	0.0213 (4)
C4	0.09652 (17)	0.07312 (14)	0.23379 (13)	0.0189 (4)
H4	0.1403	0.0886	0.1790	0.023*
C5	0.10029 (17)	0.22161 (15)	0.39038 (13)	0.0199 (4)
C6	0.27164 (17)	−0.06142 (16)	0.28186 (15)	0.0239 (4)
C7	0.3202 (2)	−0.14574 (17)	0.12533 (16)	0.0364 (5)
H7A	0.2439	−0.2201	0.0913	0.044*
H7B	0.4011	−0.1660	0.1752	0.044*
C8	0.3682 (2)	−0.09030 (19)	0.04354 (17)	0.0391 (5)
H8A	0.2880	−0.0685	−0.0041	0.059*
H8B	0.4014	−0.1483	0.0037	0.059*
H8C	0.4459	−0.0184	0.0783	0.059*
C9	−0.04382 (17)	−0.02596 (14)	0.18261 (13)	0.0181 (4)
C10	−0.07297 (18)	−0.10076 (15)	0.08378 (13)	0.0212 (4)
H10	−0.0079	−0.0867	0.0468	0.025*
C11	−0.19697 (18)	−0.19597 (15)	0.03911 (14)	0.0250 (4)
H11	−0.2141	−0.2460	−0.0267	0.030*
C12	−0.29533 (17)	−0.21597 (15)	0.09342 (14)	0.0232 (4)
C13	−0.26702 (18)	−0.14307 (16)	0.19270 (14)	0.0248 (4)
H13	−0.3321	−0.1574	0.2297	0.030*
C14	−0.14238 (17)	−0.04920 (15)	0.23686 (13)	0.0216 (4)
H14	−0.1240	−0.0009	0.3037	0.026*
C15	−0.4605 (2)	−0.3746 (2)	−0.04918 (17)	0.0525 (6)
H15A	−0.4643	−0.3196	−0.0975	0.079*
H15B	−0.5540	−0.4305	−0.0685	0.079*
H15C	−0.3891	−0.4195	−0.0531	0.079*
C16	0.00520 (17)	0.26045 (14)	0.21851 (13)	0.0182 (4)
C17	−0.02451 (17)	0.36688 (15)	0.28420 (12)	0.0179 (4)
C18	0.04721 (17)	0.49640 (14)	0.27189 (12)	0.0177 (4)
C19	0.21177 (17)	0.53663 (14)	0.31052 (13)	0.0190 (4)
C20	0.31437 (18)	0.56616 (16)	0.41158 (14)	0.0244 (4)
H20	0.2864	0.5586	0.4711	0.029*
C21	0.46058 (18)	0.60752 (16)	0.42303 (15)	0.0275 (4)
H21	0.5304	0.6264	0.4907	0.033*
C22	0.50340 (18)	0.62089 (16)	0.33501 (15)	0.0262 (4)
H22	0.6016	0.6480	0.3443	0.031*
C23	0.40141 (17)	0.59426 (15)	0.23323 (14)	0.0227 (4)
H23	0.4291	0.6039	0.1739	0.027*
C24	0.25706 (17)	0.55281 (14)	0.22340 (13)	0.0194 (4)
C25	0.00866 (18)	0.49965 (14)	0.14971 (13)	0.0187 (4)
C26	−0.18551 (17)	0.37201 (15)	0.25039 (13)	0.0197 (4)
H26	−0.2205	0.3585	0.1723	0.024*
C27	−0.17881 (17)	0.50704 (15)	0.29251 (13)	0.0208 (4)
H27A	−0.2352	0.5409	0.2364	0.025*
H27B	−0.2161	0.5145	0.3516	0.025*
C28	0.00420 (19)	0.69933 (15)	0.32462 (14)	0.0244 (4)
H28A	0.1071	0.7349	0.3524	0.037*
H28B	−0.0424	0.7401	0.3672	0.037*
H28C	−0.0334	0.7083	0.2522	0.037*
C29	−0.28448 (18)	0.27477 (16)	0.27959 (14)	0.0257 (4)
C30	−0.5040 (2)	0.22464 (19)	0.31518 (18)	0.0452 (6)
H30A	−0.5414	0.1575	0.2545	0.068*
H30B	−0.5813	0.2604	0.3225	0.068*
H30C	−0.4628	0.1956	0.3785	0.068*

	U11	U22	U33	U12	U13	U23
S1	0.0323 (3)	0.0206 (2)	0.0145 (2)	0.00589 (18)	0.00909 (19)	0.00318 (18)
O1	0.0359 (8)	0.0347 (8)	0.0425 (8)	0.0188 (6)	0.0128 (7)	0.0170 (7)
O2	0.0311 (7)	0.0284 (7)	0.0330 (7)	0.0159 (6)	0.0164 (6)	0.0083 (6)
O3	0.0246 (7)	0.0246 (7)	0.0345 (7)	−0.0027 (5)	0.0041 (6)	−0.0046 (6)
O4	0.0335 (7)	0.0232 (6)	0.0143 (6)	0.0093 (5)	0.0074 (5)	0.0024 (5)
O5	0.0213 (6)	0.0286 (7)	0.0150 (6)	0.0065 (5)	0.0048 (5)	0.0057 (5)
O6	0.0429 (8)	0.0239 (7)	0.0705 (11)	0.0051 (6)	0.0322 (8)	0.0122 (7)
O7	0.0267 (7)	0.0302 (7)	0.0435 (8)	−0.0003 (6)	0.0213 (7)	0.0026 (6)
N1	0.0255 (8)	0.0268 (8)	0.0190 (7)	0.0050 (6)	0.0058 (7)	0.0065 (7)
N2	0.0198 (7)	0.0160 (7)	0.0159 (7)	0.0036 (6)	0.0062 (6)	0.0025 (6)
N3	0.0227 (8)	0.0270 (8)	0.0153 (7)	0.0064 (6)	0.0090 (6)	0.0064 (6)
N4	0.0219 (7)	0.0164 (7)	0.0177 (7)	0.0047 (6)	0.0094 (6)	0.0019 (6)
C1	0.0336 (11)	0.0395 (11)	0.0282 (10)	0.0130 (9)	0.0036 (9)	0.0103 (9)
C2	0.0182 (9)	0.0241 (9)	0.0269 (9)	0.0038 (7)	0.0070 (8)	0.0108 (8)
C3	0.0148 (8)	0.0214 (9)	0.0276 (9)	0.0025 (7)	0.0066 (8)	0.0091 (8)
C4	0.0197 (9)	0.0181 (8)	0.0197 (8)	0.0055 (7)	0.0083 (7)	0.0019 (7)
C5	0.0212 (9)	0.0204 (9)	0.0164 (8)	0.0005 (7)	0.0066 (7)	0.0043 (7)
C6	0.0141 (9)	0.0219 (9)	0.0326 (10)	−0.0006 (7)	0.0061 (8)	0.0065 (8)
C7	0.0389 (12)	0.0299 (10)	0.0495 (13)	0.0199 (9)	0.0216 (11)	0.0070 (10)
C8	0.0419 (12)	0.0425 (12)	0.0411 (12)	0.0189 (10)	0.0223 (11)	0.0054 (10)
C9	0.0190 (9)	0.0166 (8)	0.0194 (8)	0.0070 (7)	0.0053 (7)	0.0045 (7)
C10	0.0240 (9)	0.0220 (9)	0.0203 (8)	0.0079 (7)	0.0092 (8)	0.0053 (7)
C11	0.0307 (10)	0.0217 (9)	0.0188 (9)	0.0069 (8)	0.0049 (8)	−0.0011 (8)
C12	0.0183 (9)	0.0182 (9)	0.0275 (9)	0.0042 (7)	0.0014 (8)	0.0012 (8)
C13	0.0218 (9)	0.0248 (9)	0.0295 (10)	0.0056 (7)	0.0130 (8)	0.0012 (8)
C14	0.0224 (9)	0.0192 (9)	0.0208 (9)	0.0042 (7)	0.0072 (8)	−0.0020 (7)
C15	0.0482 (14)	0.0483 (14)	0.0340 (12)	−0.0169 (11)	0.0018 (11)	−0.0114 (11)
C16	0.0169 (8)	0.0167 (8)	0.0190 (9)	0.0003 (7)	0.0063 (7)	0.0020 (7)
C17	0.0217 (9)	0.0179 (8)	0.0125 (8)	0.0025 (7)	0.0057 (7)	0.0016 (7)
C18	0.0218 (9)	0.0172 (8)	0.0138 (8)	0.0043 (7)	0.0063 (7)	0.0025 (7)
C19	0.0215 (9)	0.0155 (8)	0.0205 (9)	0.0056 (7)	0.0074 (8)	0.0034 (7)
C20	0.0283 (10)	0.0243 (9)	0.0200 (9)	0.0068 (8)	0.0069 (8)	0.0053 (8)
C21	0.0210 (9)	0.0296 (10)	0.0254 (9)	0.0060 (8)	−0.0005 (8)	0.0031 (8)
C22	0.0181 (9)	0.0233 (9)	0.0364 (10)	0.0067 (7)	0.0083 (8)	0.0037 (8)
C23	0.0231 (9)	0.0210 (9)	0.0261 (9)	0.0065 (7)	0.0117 (8)	0.0025 (8)
C24	0.0232 (9)	0.0163 (8)	0.0189 (8)	0.0063 (7)	0.0069 (7)	0.0027 (7)
C25	0.0258 (10)	0.0146 (8)	0.0165 (8)	0.0046 (7)	0.0088 (8)	0.0025 (7)
C26	0.0198 (9)	0.0202 (9)	0.0185 (8)	0.0029 (7)	0.0075 (7)	0.0019 (7)
C27	0.0230 (9)	0.0222 (9)	0.0186 (8)	0.0062 (7)	0.0091 (8)	0.0032 (7)
C28	0.0300 (10)	0.0185 (9)	0.0255 (9)	0.0059 (7)	0.0106 (8)	0.0048 (8)
C29	0.0270 (10)	0.0255 (10)	0.0241 (9)	0.0035 (8)	0.0114 (8)	0.0012 (8)
C30	0.0389 (12)	0.0398 (12)	0.0564 (14)	−0.0091 (10)	0.0317 (12)	−0.0001 (11)

S1—C5	1.7542 (17)	C9—C14	1.393 (2)
S1—C17	1.8239 (17)	C10—C11	1.386 (2)
O1—C6	1.204 (2)	C10—H10	0.9300
O2—C6	1.347 (2)	C11—C12	1.388 (2)
O2—C7	1.4547 (19)	C11—H11	0.9300
O3—C12	1.375 (2)	C12—C13	1.386 (2)
O3—C15	1.417 (2)	C13—C14	1.382 (2)
O4—C16	1.2092 (19)	C13—H13	0.9300
O5—C25	1.225 (2)	C14—H14	0.9300
O6—C29	1.195 (2)	C15—H15A	0.9600
O7—C29	1.336 (2)	C15—H15B	0.9600
O7—C30	1.449 (2)	C15—H15C	0.9600
N1—C5	1.279 (2)	C16—C17	1.525 (2)
N1—C2	1.418 (2)	C17—C26	1.543 (2)
N2—C16	1.372 (2)	C17—C18	1.565 (2)
N2—C5	1.386 (2)	C18—C19	1.516 (2)
N2—C4	1.4763 (19)	C18—C25	1.576 (2)
N3—C25	1.351 (2)	C19—C20	1.381 (2)
N3—C24	1.410 (2)	C19—C24	1.395 (2)
N3—H3	0.8600	C20—C21	1.394 (2)
N4—C28	1.456 (2)	C20—H20	0.9300
N4—C18	1.4613 (19)	C21—C22	1.387 (2)
N4—C27	1.468 (2)	C21—H21	0.9300
C1—C2	1.489 (3)	C22—C23	1.387 (2)
C1—H1A	0.9600	C22—H22	0.9300
C1—H1B	0.9600	C23—C24	1.383 (2)
C1—H1C	0.9600	C23—H23	0.9300
C2—C3	1.354 (2)	C26—C29	1.511 (2)
C3—C6	1.488 (2)	C26—C27	1.544 (2)
C3—C4	1.522 (2)	C26—H26	0.9800
C4—C9	1.517 (2)	C27—H27A	0.9700
C4—H4	0.9800	C27—H27B	0.9700
C7—C8	1.490 (3)	C28—H28A	0.9600
C7—H7A	0.9700	C28—H28B	0.9600
C7—H7B	0.9700	C28—H28C	0.9600
C8—H8A	0.9600	C30—H30A	0.9600
C8—H8B	0.9600	C30—H30B	0.9600
C8—H8C	0.9600	C30—H30C	0.9600
C9—C10	1.388 (2)
C5—S1—C17	92.62 (8)	O3—C15—H15B	109.5
C6—O2—C7	118.23 (14)	H15A—C15—H15B	109.5
C12—O3—C15	116.59 (14)	O3—C15—H15C	109.5
C29—O7—C30	115.34 (15)	H15A—C15—H15C	109.5
C5—N1—C2	116.85 (14)	H15B—C15—H15C	109.5
C16—N2—C5	117.35 (13)	O4—C16—N2	123.53 (14)
C16—N2—C4	121.33 (13)	O4—C16—C17	124.42 (15)
C5—N2—C4	120.99 (14)	N2—C16—C17	112.04 (13)
C25—N3—C24	112.18 (13)	C16—C17—C26	114.29 (13)
C25—N3—H3	123.9	C16—C17—C18	114.60 (12)
C24—N3—H3	123.9	C26—C17—C18	100.14 (13)
C28—N4—C18	116.07 (12)	C16—C17—S1	106.54 (11)
C28—N4—C27	114.43 (13)	C26—C17—S1	110.98 (11)
C18—N4—C27	107.91 (12)	C18—C17—S1	110.29 (11)
C2—C1—H1A	109.5	N4—C18—C19	115.48 (13)
C2—C1—H1B	109.5	N4—C18—C17	99.08 (11)
H1A—C1—H1B	109.5	C19—C18—C17	117.85 (14)
C2—C1—H1C	109.5	N4—C18—C25	113.92 (13)
H1A—C1—H1C	109.5	C19—C18—C25	101.49 (12)
H1B—C1—H1C	109.5	C17—C18—C25	109.54 (13)
C3—C2—N1	122.34 (16)	C20—C19—C24	119.01 (15)
C3—C2—C1	126.15 (16)	C20—C19—C18	131.99 (14)
N1—C2—C1	111.49 (15)	C24—C19—C18	108.80 (14)
C2—C3—C6	123.73 (17)	C19—C20—C21	118.98 (16)
C2—C3—C4	121.49 (15)	C19—C20—H20	120.5
C6—C3—C4	114.66 (14)	C21—C20—H20	120.5
N2—C4—C9	111.87 (12)	C22—C21—C20	121.00 (17)
N2—C4—C3	108.35 (13)	C22—C21—H21	119.5
C9—C4—C3	110.37 (13)	C20—C21—H21	119.5
N2—C4—H4	108.7	C23—C22—C21	120.73 (15)
C9—C4—H4	108.7	C23—C22—H22	119.6
C3—C4—H4	108.7	C21—C22—H22	119.6
N1—C5—N2	126.15 (15)	C24—C23—C22	117.44 (15)
N1—C5—S1	122.36 (13)	C24—C23—H23	121.3
N2—C5—S1	111.45 (13)	C22—C23—H23	121.3
O1—C6—O2	123.06 (16)	C23—C24—C19	122.81 (16)
O1—C6—C3	127.42 (17)	C23—C24—N3	127.24 (15)
O2—C6—C3	109.52 (15)	C19—C24—N3	109.84 (14)
O2—C7—C8	107.49 (15)	O5—C25—N3	126.46 (15)
O2—C7—H7A	110.2	O5—C25—C18	125.94 (13)
C8—C7—H7A	110.2	N3—C25—C18	107.53 (14)
O2—C7—H7B	110.2	C29—C26—C17	115.01 (14)
C8—C7—H7B	110.2	C29—C26—C27	117.66 (13)
H7A—C7—H7B	108.5	C17—C26—C27	103.79 (13)
C7—C8—H8A	109.5	C29—C26—H26	106.5
C7—C8—H8B	109.5	C17—C26—H26	106.5
H8A—C8—H8B	109.5	C27—C26—H26	106.5
C7—C8—H8C	109.5	N4—C27—C26	104.93 (13)
H8A—C8—H8C	109.5	N4—C27—H27A	110.8
H8B—C8—H8C	109.5	C26—C27—H27A	110.8
C10—C9—C14	118.29 (14)	N4—C27—H27B	110.8
C10—C9—C4	120.96 (13)	C26—C27—H27B	110.8
C14—C9—C4	120.62 (14)	H27A—C27—H27B	108.8
C11—C10—C9	121.39 (15)	N4—C28—H28A	109.5
C11—C10—H10	119.3	N4—C28—H28B	109.5
C9—C10—H10	119.3	H28A—C28—H28B	109.5
C10—C11—C12	119.42 (15)	N4—C28—H28C	109.5
C10—C11—H11	120.3	H28A—C28—H28C	109.5
C12—C11—H11	120.3	H28B—C28—H28C	109.5
O3—C12—C13	115.67 (15)	O6—C29—O7	124.42 (16)
O3—C12—C11	124.42 (15)	O6—C29—C26	124.14 (15)
C13—C12—C11	119.90 (15)	O7—C29—C26	111.27 (15)
C14—C13—C12	120.14 (15)	O7—C30—H30A	109.5
C14—C13—H13	119.9	O7—C30—H30B	109.5
C12—C13—H13	119.9	H30A—C30—H30B	109.5
C13—C14—C9	120.84 (15)	O7—C30—H30C	109.5
C13—C14—H14	119.6	H30A—C30—H30C	109.5
C9—C14—H14	119.6	H30B—C30—H30C	109.5
O3—C15—H15A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O5i	0.86	1.97	2.8189 (18)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O5i	0.86	1.97	2.8189 (18)	169

Symmetry code: (i) .