3',7',7'-Trimethyl-1'-phenyl-5',6',7',8'-tetra-hydro-spiro-[indoline-3,4'-(1H,4H-pyrazolo-[3,4-b]chromene)]-2,5'-dione.

The title spiro-oxindole compound, C(26)H(23)N(3)O(3), was prepared by the reaction of isatin, 3-methyl-1-phenyl-2-pyrazolin-5-one and 5,5-dimethyl-cyclo-hexane-1,3-dione in an ethanol solution. The fused cyclo-hexene ring adopts an envelope conformation. The dihedral angle between the aromatic and pyrazoline rings is 23.70 (8)°. An intra-molecular C-H⋯O inter-action occurs. The crystal structure is stabilized by N-H⋯N hydrogen-bonding inter-actions, leading to a zigzag chain along the b axis.

Related literature

For general background to spiro compounds and their bio­logical activity, see: Li et al. (2010 ▶); Shemchuk et al. (2008 ▶); Zhang & Panek (2009 ▶); Zhu et al. (2007 ▶).

Experimental

Crystal data

C26H23N3O3

M = 425.47

Monoclinic,

a = 11.8778 (19) Å

b = 12.891 (2) Å

c = 14.039 (2) Å

β = 100.280 (3)°

V = 2115.1 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 110 K

0.46 × 0.40 × 0.39 mm

Data collection

Bruker SMART CCD 1K area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.960, T max = 0.966

9755 measured reflections

4085 independent reflections

3097 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.102

S = 1.05

4085 reflections

292 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT-Plus (Bruker, 1999 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810045253/vm2051sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045253/vm2051Isup2.hkl

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

C26H23N3O3	F(000) = 896
Mr = 425.47	Dx = 1.336 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4524 reflections
a = 11.8778 (19) Å	θ = 2.2–27.0°
b = 12.891 (2) Å	µ = 0.09 mm−1
c = 14.039 (2) Å	T = 110 K
β = 100.280 (3)°	Block, colorless
V = 2115.1 (6) Å3	0.46 × 0.40 × 0.39 mm
Z = 4

Bruker SMART CCD 1K area-detector diffractometer	4085 independent reflections
Radiation source: fine-focus sealed tube	3097 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.960, Tmax = 0.966	k = −15→13
9755 measured reflections	l = −17→10

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0527P)2 + 0.4259P] where P = (Fo2 + 2Fc2)/3
4085 reflections	(Δ/σ)max < 0.001
292 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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
C1	−0.13468 (13)	0.10606 (12)	0.24814 (11)	0.0200 (3)
C2	−0.04964 (12)	0.17757 (12)	0.23366 (10)	0.0168 (3)
C3	0.02151 (12)	0.12204 (11)	0.18767 (10)	0.0170 (3)
C4	−0.02884 (13)	0.28932 (11)	0.26016 (10)	0.0172 (3)
C5	0.07068 (13)	0.32491 (12)	0.21352 (10)	0.0178 (3)
C6	0.13557 (13)	0.26188 (11)	0.16884 (10)	0.0179 (3)
C7	0.09785 (13)	0.43675 (12)	0.21781 (10)	0.0193 (3)
C8	0.20736 (13)	0.47098 (12)	0.18694 (11)	0.0212 (3)
H8A	0.2714	0.4627	0.2422	0.025*
H8B	0.2014	0.5456	0.1700	0.025*
C9	0.23482 (13)	0.41005 (12)	0.10033 (11)	0.0193 (3)
C10	0.23633 (13)	0.29460 (12)	0.12630 (11)	0.0207 (3)
H10A	0.2383	0.2533	0.0672	0.025*
H10B	0.3071	0.2793	0.1731	0.025*
C11	0.03029 (13)	−0.06572 (11)	0.13607 (11)	0.0185 (3)
C12	0.10268 (13)	−0.05500 (12)	0.06905 (11)	0.0205 (3)
H12	0.1237	0.0120	0.0501	0.025*
C13	0.14373 (13)	−0.14305 (12)	0.03029 (11)	0.0233 (4)
H13	0.1927	−0.1364	−0.0160	0.028*
C14	0.11399 (14)	−0.24068 (13)	0.05836 (12)	0.0275 (4)
H14	0.1416	−0.3008	0.0308	0.033*
C15	0.04423 (15)	−0.25055 (13)	0.12654 (12)	0.0267 (4)
H15	0.0254	−0.3176	0.1469	0.032*
C16	0.00131 (14)	−0.16334 (12)	0.16572 (11)	0.0224 (4)
H16	−0.0473	−0.1704	0.2122	0.027*
C17	−0.14039 (13)	0.35270 (11)	0.22569 (11)	0.0192 (3)
C18	−0.10051 (13)	0.36495 (11)	0.39106 (11)	0.0204 (3)
C19	−0.01059 (13)	0.30626 (11)	0.36897 (10)	0.0180 (3)
C20	−0.10638 (15)	0.39146 (13)	0.48573 (12)	0.0259 (4)
H20	−0.1673	0.4327	0.5005	0.031*
C21	−0.01995 (15)	0.35545 (13)	0.55838 (12)	0.0287 (4)
H21	−0.0214	0.3731	0.6238	0.034*
C22	0.06789 (15)	0.29442 (13)	0.53702 (12)	0.0282 (4)
H22	0.1250	0.2694	0.5879	0.034*
C23	0.07337 (13)	0.26930 (12)	0.44129 (11)	0.0226 (4)
H23	0.1338	0.2276	0.4264	0.027*
C24	−0.23692 (14)	0.12431 (13)	0.29448 (12)	0.0267 (4)
H24A	−0.2972	0.1581	0.2480	0.040*
H24B	−0.2155	0.1690	0.3513	0.040*
H24C	−0.2651	0.0578	0.3145	0.040*
C25	0.14278 (14)	0.43141 (13)	0.01188 (11)	0.0247 (4)
H25A	0.1557	0.3871	−0.0418	0.037*
H25B	0.1463	0.5044	−0.0069	0.037*
H25C	0.0673	0.4165	0.0276	0.037*
C26	0.35231 (14)	0.44152 (13)	0.07888 (12)	0.0252 (4)
H26A	0.4105	0.4318	0.1371	0.038*
H26B	0.3505	0.5146	0.0594	0.038*
H26C	0.3710	0.3983	0.0264	0.038*
N1	−0.01647 (11)	0.02305 (10)	0.17519 (9)	0.0180 (3)
N2	−0.11516 (11)	0.01329 (10)	0.21348 (9)	0.0205 (3)
N3	−0.17731 (11)	0.38803 (10)	0.30610 (9)	0.0227 (3)
H3	−0.2421	0.4216	0.3048	0.027*
O1	0.03312 (10)	0.49811 (8)	0.24678 (8)	0.0264 (3)
O2	0.11714 (9)	0.15614 (8)	0.15647 (7)	0.0199 (2)
O3	−0.18860 (9)	0.36251 (9)	0.14228 (8)	0.0260 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0206 (8)	0.0224 (8)	0.0170 (7)	−0.0002 (7)	0.0031 (6)	−0.0006 (6)
C2	0.0164 (8)	0.0186 (8)	0.0155 (7)	0.0007 (6)	0.0030 (6)	0.0011 (6)
C3	0.0156 (7)	0.0172 (8)	0.0181 (7)	0.0002 (6)	0.0030 (6)	0.0016 (6)
C4	0.0166 (8)	0.0167 (8)	0.0188 (8)	0.0004 (6)	0.0048 (6)	0.0001 (6)
C5	0.0171 (8)	0.0196 (8)	0.0166 (7)	0.0000 (6)	0.0025 (6)	0.0013 (6)
C6	0.0189 (8)	0.0148 (8)	0.0195 (8)	−0.0007 (6)	0.0020 (6)	0.0009 (6)
C7	0.0233 (8)	0.0206 (8)	0.0136 (7)	0.0000 (7)	0.0020 (6)	−0.0005 (6)
C8	0.0224 (8)	0.0192 (8)	0.0221 (8)	−0.0031 (6)	0.0040 (7)	−0.0023 (6)
C9	0.0195 (8)	0.0183 (8)	0.0213 (8)	−0.0028 (6)	0.0067 (6)	−0.0003 (6)
C10	0.0178 (8)	0.0205 (8)	0.0251 (8)	−0.0006 (6)	0.0074 (7)	−0.0012 (6)
C11	0.0170 (7)	0.0175 (8)	0.0190 (8)	0.0021 (6)	−0.0018 (6)	−0.0031 (6)
C12	0.0200 (8)	0.0215 (8)	0.0189 (8)	0.0002 (6)	0.0002 (6)	0.0006 (6)
C13	0.0190 (8)	0.0273 (9)	0.0229 (8)	0.0028 (7)	0.0018 (7)	−0.0044 (7)
C14	0.0248 (9)	0.0239 (9)	0.0318 (9)	0.0049 (7)	−0.0002 (7)	−0.0088 (7)
C15	0.0281 (9)	0.0173 (8)	0.0327 (9)	−0.0021 (7)	0.0002 (7)	−0.0021 (7)
C16	0.0216 (8)	0.0215 (8)	0.0230 (8)	−0.0017 (7)	0.0013 (7)	0.0001 (6)
C17	0.0188 (8)	0.0153 (8)	0.0246 (8)	−0.0004 (6)	0.0070 (7)	0.0024 (6)
C18	0.0227 (8)	0.0156 (8)	0.0243 (8)	−0.0018 (6)	0.0079 (7)	−0.0001 (6)
C19	0.0196 (8)	0.0159 (8)	0.0198 (8)	−0.0045 (6)	0.0075 (6)	−0.0021 (6)
C20	0.0320 (10)	0.0197 (8)	0.0304 (9)	−0.0023 (7)	0.0171 (8)	−0.0052 (7)
C21	0.0369 (10)	0.0311 (10)	0.0200 (8)	−0.0106 (8)	0.0100 (7)	−0.0073 (7)
C22	0.0299 (10)	0.0317 (10)	0.0218 (8)	−0.0067 (8)	0.0014 (7)	−0.0010 (7)
C23	0.0195 (8)	0.0234 (9)	0.0250 (8)	−0.0017 (7)	0.0045 (7)	−0.0005 (6)
C24	0.0255 (9)	0.0275 (9)	0.0302 (9)	−0.0040 (7)	0.0129 (7)	−0.0043 (7)
C25	0.0233 (8)	0.0303 (9)	0.0213 (8)	−0.0005 (7)	0.0061 (7)	0.0018 (7)
C26	0.0226 (9)	0.0253 (9)	0.0292 (9)	−0.0033 (7)	0.0086 (7)	−0.0011 (7)
N1	0.0176 (7)	0.0170 (7)	0.0206 (7)	−0.0008 (5)	0.0063 (5)	−0.0005 (5)
N2	0.0193 (7)	0.0216 (7)	0.0219 (7)	−0.0026 (5)	0.0075 (5)	−0.0016 (5)
N3	0.0204 (7)	0.0217 (7)	0.0280 (7)	0.0065 (6)	0.0095 (6)	0.0025 (6)
O1	0.0321 (7)	0.0195 (6)	0.0309 (6)	0.0012 (5)	0.0145 (5)	−0.0034 (5)
O2	0.0178 (6)	0.0154 (5)	0.0284 (6)	−0.0006 (4)	0.0095 (5)	−0.0013 (4)
O3	0.0247 (6)	0.0285 (7)	0.0237 (6)	0.0039 (5)	0.0017 (5)	0.0043 (5)

C1—N2	1.327 (2)	C13—H13	0.9500
C1—C2	1.409 (2)	C14—C15	1.379 (2)
C1—C24	1.495 (2)	C14—H14	0.9500
C2—C3	1.356 (2)	C15—C16	1.388 (2)
C2—C4	1.497 (2)	C15—H15	0.9500
C3—N1	1.3543 (19)	C16—H16	0.9500
C3—O2	1.3612 (17)	C17—O3	1.2148 (18)
C4—C19	1.520 (2)	C17—N3	1.3606 (19)
C4—C5	1.521 (2)	C18—C20	1.386 (2)
C4—C17	1.558 (2)	C18—C19	1.388 (2)
C5—C6	1.349 (2)	C18—N3	1.398 (2)
C5—C7	1.476 (2)	C19—C23	1.375 (2)
C6—O2	1.3866 (18)	C20—C21	1.391 (2)
C6—C10	1.491 (2)	C20—H20	0.9500
C7—O1	1.2223 (18)	C21—C22	1.382 (2)
C7—C8	1.509 (2)	C21—H21	0.9500
C8—C9	1.531 (2)	C22—C23	1.395 (2)
C8—H8A	0.9900	C22—H22	0.9500
C8—H8B	0.9900	C23—H23	0.9500
C9—C25	1.526 (2)	C24—H24A	0.9800
C9—C10	1.532 (2)	C24—H24B	0.9800
C9—C26	1.534 (2)	C24—H24C	0.9800
C10—H10A	0.9900	C25—H25A	0.9800
C10—H10B	0.9900	C25—H25B	0.9800
C11—C16	1.388 (2)	C25—H25C	0.9800
C11—C12	1.390 (2)	C26—H26A	0.9800
C11—N1	1.4243 (19)	C26—H26B	0.9800
C12—C13	1.385 (2)	C26—H26C	0.9800
C12—H12	0.9500	N1—N2	1.3798 (17)
C13—C14	1.383 (2)	N3—H3	0.8800
N2—C1—C2	111.11 (13)	C14—C15—C16	120.59 (15)
N2—C1—C24	120.66 (14)	C14—C15—H15	119.7
C2—C1—C24	128.23 (14)	C16—C15—H15	119.7
C3—C2—C1	104.30 (13)	C11—C16—C15	119.16 (15)
C3—C2—C4	122.48 (13)	C11—C16—H16	120.4
C1—C2—C4	133.20 (13)	C15—C16—H16	120.4
N1—C3—C2	109.73 (13)	O3—C17—N3	126.78 (14)
N1—C3—O2	122.72 (13)	O3—C17—C4	125.62 (13)
C2—C3—O2	127.55 (14)	N3—C17—C4	107.45 (12)
C2—C4—C19	112.06 (12)	C20—C18—C19	121.39 (15)
C2—C4—C5	106.84 (12)	C20—C18—N3	128.96 (15)
C19—C4—C5	114.02 (12)	C19—C18—N3	109.64 (13)
C2—C4—C17	109.50 (12)	C23—C19—C18	120.61 (14)
C19—C4—C17	101.41 (12)	C23—C19—C4	130.31 (14)
C5—C4—C17	113.03 (12)	C18—C19—C4	108.99 (13)
C6—C5—C7	117.92 (14)	C18—C20—C21	117.64 (15)
C6—C5—C4	124.82 (14)	C18—C20—H20	121.2
C7—C5—C4	117.27 (13)	C21—C20—H20	121.2
C5—C6—O2	124.03 (13)	C22—C21—C20	121.19 (15)
C5—C6—C10	125.59 (14)	C22—C21—H21	119.4
O2—C6—C10	110.37 (12)	C20—C21—H21	119.4
O1—C7—C5	119.98 (14)	C21—C22—C23	120.53 (16)
O1—C7—C8	122.15 (14)	C21—C22—H22	119.7
C5—C7—C8	117.87 (13)	C23—C22—H22	119.7
C7—C8—C9	113.26 (12)	C19—C23—C22	118.59 (15)
C7—C8—H8A	108.9	C19—C23—H23	120.7
C9—C8—H8A	108.9	C22—C23—H23	120.7
C7—C8—H8B	108.9	C1—C24—H24A	109.5
C9—C8—H8B	108.9	C1—C24—H24B	109.5
H8A—C8—H8B	107.7	H24A—C24—H24B	109.5
C25—C9—C8	109.30 (13)	C1—C24—H24C	109.5
C25—C9—C10	110.20 (13)	H24A—C24—H24C	109.5
C8—C9—C10	107.73 (12)	H24B—C24—H24C	109.5
C25—C9—C26	109.71 (13)	C9—C25—H25A	109.5
C8—C9—C26	110.52 (13)	C9—C25—H25B	109.5
C10—C9—C26	109.35 (13)	H25A—C25—H25B	109.5
C6—C10—C9	113.21 (13)	C9—C25—H25C	109.5
C6—C10—H10A	108.9	H25A—C25—H25C	109.5
C9—C10—H10A	108.9	H25B—C25—H25C	109.5
C6—C10—H10B	108.9	C9—C26—H26A	109.5
C9—C10—H10B	108.9	C9—C26—H26B	109.5
H10A—C10—H10B	107.7	H26A—C26—H26B	109.5
C16—C11—C12	120.63 (14)	C9—C26—H26C	109.5
C16—C11—N1	118.57 (14)	H26A—C26—H26C	109.5
C12—C11—N1	120.79 (14)	H26B—C26—H26C	109.5
C13—C12—C11	119.23 (15)	C3—N1—N2	108.79 (12)
C13—C12—H12	120.4	C3—N1—C11	131.54 (13)
C11—C12—H12	120.4	N2—N1—C11	119.59 (12)
C14—C13—C12	120.54 (15)	C1—N2—N1	106.07 (12)
C14—C13—H13	119.7	C17—N3—C18	112.26 (13)
C12—C13—H13	119.7	C17—N3—H3	123.9
C15—C14—C13	119.82 (15)	C18—N3—H3	123.9
C15—C14—H14	120.1	C3—O2—C6	113.54 (11)
C13—C14—H14	120.1
N2—C1—C2—C3	0.37 (17)	C14—C15—C16—C11	−0.6 (2)
C24—C1—C2—C3	−179.09 (15)	C2—C4—C17—O3	−61.79 (19)
N2—C1—C2—C4	−178.23 (15)	C19—C4—C17—O3	179.66 (14)
C24—C1—C2—C4	2.3 (3)	C5—C4—C17—O3	57.2 (2)
C1—C2—C3—N1	−0.38 (16)	C2—C4—C17—N3	113.94 (13)
C4—C2—C3—N1	178.42 (13)	C19—C4—C17—N3	−4.61 (15)
C1—C2—C3—O2	179.22 (14)	C5—C4—C17—N3	−127.08 (13)
C4—C2—C3—O2	−2.0 (2)	C20—C18—C19—C23	2.5 (2)
C3—C2—C4—C19	−117.71 (15)	N3—C18—C19—C23	−176.67 (13)
C1—C2—C4—C19	60.7 (2)	C20—C18—C19—C4	179.44 (14)
C3—C2—C4—C5	7.85 (19)	N3—C18—C19—C4	0.28 (17)
C1—C2—C4—C5	−173.75 (15)	C2—C4—C19—C23	62.4 (2)
C3—C2—C4—C17	130.58 (15)	C5—C4—C19—C23	−59.1 (2)
C1—C2—C4—C17	−51.0 (2)	C17—C4—C19—C23	179.12 (15)
C2—C4—C5—C6	−8.21 (19)	C2—C4—C19—C18	−114.12 (14)
C19—C4—C5—C6	116.16 (16)	C5—C4—C19—C18	124.35 (14)
C17—C4—C5—C6	−128.71 (15)	C17—C4—C19—C18	2.56 (15)
C2—C4—C5—C7	171.85 (12)	C19—C18—C20—C21	−1.2 (2)
C19—C4—C5—C7	−63.78 (17)	N3—C18—C20—C21	177.76 (15)
C17—C4—C5—C7	51.35 (17)	C18—C20—C21—C22	−0.7 (2)
C7—C5—C6—O2	−177.59 (13)	C20—C21—C22—C23	1.5 (3)
C4—C5—C6—O2	2.5 (2)	C18—C19—C23—C22	−1.7 (2)
C7—C5—C6—C10	2.6 (2)	C4—C19—C23—C22	−177.94 (15)
C4—C5—C6—C10	−177.33 (14)	C21—C22—C23—C19	−0.2 (2)
C6—C5—C7—O1	171.01 (14)	C2—C3—N1—N2	0.26 (16)
C4—C5—C7—O1	−9.1 (2)	O2—C3—N1—N2	−179.36 (13)
C6—C5—C7—C8	−9.8 (2)	C2—C3—N1—C11	−176.30 (14)
C4—C5—C7—C8	170.11 (13)	O2—C3—N1—C11	4.1 (2)
O1—C7—C8—C9	−143.11 (15)	C16—C11—N1—C3	154.44 (15)
C5—C7—C8—C9	37.76 (19)	C12—C11—N1—C3	−26.1 (2)
C7—C8—C9—C25	64.51 (17)	C16—C11—N1—N2	−21.8 (2)
C7—C8—C9—C10	−55.24 (17)	C12—C11—N1—N2	157.68 (13)
C7—C8—C9—C26	−174.65 (13)	C2—C1—N2—N1	−0.22 (16)
C5—C6—C10—C9	−23.1 (2)	C24—C1—N2—N1	179.28 (13)
O2—C6—C10—C9	157.05 (12)	C3—N1—N2—C1	−0.02 (16)
C25—C9—C10—C6	−71.83 (16)	C11—N1—N2—C1	177.02 (12)
C8—C9—C10—C6	47.34 (17)	O3—C17—N3—C18	−179.12 (15)
C26—C9—C10—C6	167.49 (13)	C4—C17—N3—C18	5.21 (16)
C16—C11—C12—C13	1.5 (2)	C20—C18—N3—C17	177.31 (15)
N1—C11—C12—C13	−178.02 (13)	C19—C18—N3—C17	−3.61 (18)
C11—C12—C13—C14	−0.5 (2)	N1—C3—O2—C6	174.73 (13)
C12—C13—C14—C15	−0.9 (2)	C2—C3—O2—C6	−4.8 (2)
C13—C14—C15—C16	1.5 (2)	C5—C6—O2—C3	4.5 (2)
C12—C11—C16—C15	−0.9 (2)	C10—C6—O2—C3	−175.68 (12)
N1—C11—C16—C15	178.57 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N2i	0.88	2.05	2.9185 (18)	172
C12—H12···O2	0.95	2.39	2.9780 (19)	119

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N2i	0.88	2.05	2.9185 (18)	172
C12—H12⋯O2	0.95	2.39	2.9780 (19)	119

Symmetry code: (i) .