1'-Methyl-4'-(4-methyl-phen-yl)dispiro-[1-benzopyran-3(4H),3'-pyrrolidine-2',3''-indoline]-2,2''-dione.

In the title compound, C(27)H(24)N(2)O(3), the pyrroldine ring adopts a twist conformation, while the six-membered pyran-one ring of the coumarin ring system is in a sofa conformation. In the crystal, pairs of N-H⋯O hydrogen bonds link the mol-ecules into inversion R(2) (2)(8) dimers. These dimers are further connected via C-H⋯O hydrogen bonds.

Related literature

For applications of pyrrolidine derivatives, see: Huryn et al. (1991 ▶); Suzuki et al. (1994 ▶); Waldmann (1995 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶) and for asymmetry parameters, see: Duax et al. (1976 ▶). For closely related pyrrolidine structures, see: Selvanayagam et al. (2011 ▶); Ali et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C27H24N2O3

M = 424.48

Monoclinic,

a = 10.4543 (3) Å

b = 14.6018 (4) Å

c = 14.7266 (4) Å

β = 104.043 (2)°

V = 2180.85 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.26 × 0.23 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.978, T max = 0.985

30221 measured reflections

7055 independent reflections

4544 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.153

S = 1.02

7055 reflections

291 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811051440/bt5735sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051440/bt5735Isup2.hkl

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

C27H24N2O3	F(000) = 896
Mr = 424.48	Dx = 1.293 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7063 reflections
a = 10.4543 (3) Å	θ = 2.0–31.2°
b = 14.6018 (4) Å	µ = 0.09 mm−1
c = 14.7266 (4) Å	T = 293 K
β = 104.043 (2)°	Block, colourless
V = 2180.85 (10) Å3	0.26 × 0.23 × 0.18 mm
Z = 4

Bruker APEXII CCD diffractometer	7055 independent reflections
Radiation source: fine-focus sealed tube	4544 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 10.0 pixels mm-1	θmax = 31.2°, θmin = 2.0°
ω scans	h = −15→14
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −21→21
Tmin = 0.978, Tmax = 0.985	l = −20→21
30221 measured reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0694P)2 + 0.398P] where P = (Fo2 + 2Fc2)/3
7055 reflections	(Δ/σ)max < 0.001
291 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.23 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 > 2sigma(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	0.80511 (12)	0.84780 (8)	0.09959 (8)	0.0326 (2)
C2	0.80733 (12)	0.86879 (8)	0.20643 (8)	0.0335 (2)
C3	0.65980 (12)	0.89026 (9)	0.20385 (9)	0.0367 (3)
H3	0.6207	0.8333	0.2197	0.044*
C4	0.59877 (13)	0.90885 (11)	0.10112 (10)	0.0449 (3)
H4A	0.5042	0.8989	0.0858	0.054*
H4B	0.6166	0.9709	0.0841	0.054*
C5	0.63008 (17)	0.84632 (12)	−0.04637 (10)	0.0548 (4)
H5A	0.5385	0.8313	−0.0695	0.082*
H5B	0.6830	0.8033	−0.0705	0.082*
H5C	0.6459	0.9070	−0.0662	0.082*
C6	0.87724 (13)	0.92422 (9)	0.05686 (9)	0.0383 (3)
C7	0.97873 (13)	0.79028 (9)	0.03856 (9)	0.0382 (3)
C8	1.06331 (16)	0.72827 (11)	0.01407 (11)	0.0528 (4)
H8	1.1311	0.7470	−0.0125	0.063*
C9	1.04343 (19)	0.63686 (12)	0.03057 (13)	0.0626 (5)
H9	1.1002	0.5932	0.0161	0.075*
C10	0.94146 (19)	0.60908 (10)	0.06787 (12)	0.0586 (4)
H10	0.9291	0.5469	0.0767	0.070*
C11	0.85666 (16)	0.67219 (9)	0.09259 (10)	0.0455 (3)
H11	0.7871	0.6532	0.1172	0.055*
C12	0.87840 (13)	0.76409 (8)	0.07963 (8)	0.0348 (3)
C13	0.90158 (13)	0.94596 (10)	0.25105 (10)	0.0450 (3)
H13A	0.8788	1.0018	0.2152	0.054*
H13B	0.8931	0.9573	0.3142	0.054*
C14	1.04058 (14)	0.91967 (12)	0.25330 (11)	0.0520 (4)
C15	1.13597 (18)	0.97997 (16)	0.23772 (14)	0.0717 (6)
H15	1.1152	1.0414	0.2254	0.086*
C16	1.2617 (2)	0.9486 (2)	0.24059 (18)	0.0957 (8)
H16	1.3259	0.9893	0.2313	0.115*
C17	1.2920 (2)	0.8584 (2)	0.2570 (2)	0.1000 (9)
H17	1.3766	0.8380	0.2578	0.120*
C18	1.19962 (18)	0.79673 (18)	0.27257 (14)	0.0791 (6)
H18	1.2205	0.7352	0.2840	0.095*
C19	1.07479 (14)	0.82966 (13)	0.27055 (10)	0.0544 (4)
C20	0.85238 (14)	0.78283 (10)	0.26401 (9)	0.0418 (3)
C21	0.63774 (12)	0.96203 (9)	0.27238 (10)	0.0395 (3)
C22	0.64635 (16)	0.93919 (11)	0.36474 (11)	0.0509 (4)
H22	0.6657	0.8791	0.3843	0.061*
C23	0.62671 (17)	1.00382 (13)	0.42869 (12)	0.0584 (4)
H23	0.6352	0.9864	0.4906	0.070*
C24	0.59504 (15)	1.09288 (12)	0.40314 (13)	0.0560 (4)
C25	0.5856 (2)	1.11562 (12)	0.31114 (15)	0.0677 (5)
H25	0.5637	1.1754	0.2915	0.081*
C26	0.60777 (18)	1.05209 (11)	0.24708 (12)	0.0576 (4)
H26	0.6024	1.0703	0.1858	0.069*
C27	0.5729 (2)	1.16348 (15)	0.47218 (17)	0.0806 (6)
H27A	0.6150	1.2198	0.4624	0.121*
H27B	0.6095	1.1420	0.5347	0.121*
H27C	0.4800	1.1737	0.4635	0.121*
N1	0.66462 (11)	0.84226 (8)	0.05524 (8)	0.0395 (2)
N2	0.97478 (11)	0.88502 (8)	0.02528 (8)	0.0430 (3)
H2	1.0282	0.9148	0.0000	0.052*
O1	0.84748 (11)	1.00547 (6)	0.05046 (8)	0.0525 (3)
O2	0.98473 (10)	0.76670 (8)	0.29036 (7)	0.0546 (3)
O3	0.78215 (12)	0.72821 (8)	0.28723 (8)	0.0607 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0345 (6)	0.0302 (6)	0.0358 (6)	−0.0025 (4)	0.0135 (5)	0.0040 (4)
C2	0.0307 (6)	0.0370 (6)	0.0351 (6)	−0.0028 (5)	0.0122 (5)	0.0013 (5)
C3	0.0304 (6)	0.0405 (6)	0.0426 (7)	−0.0013 (5)	0.0154 (5)	0.0039 (5)
C4	0.0343 (6)	0.0549 (8)	0.0459 (7)	0.0033 (6)	0.0108 (6)	0.0029 (6)
C5	0.0553 (9)	0.0659 (10)	0.0397 (7)	0.0022 (7)	0.0051 (6)	0.0038 (7)
C6	0.0412 (7)	0.0345 (6)	0.0434 (7)	−0.0018 (5)	0.0184 (5)	0.0055 (5)
C7	0.0409 (7)	0.0403 (7)	0.0343 (6)	0.0031 (5)	0.0110 (5)	−0.0006 (5)
C8	0.0489 (8)	0.0610 (10)	0.0504 (8)	0.0121 (7)	0.0157 (7)	−0.0087 (7)
C9	0.0666 (11)	0.0519 (9)	0.0654 (10)	0.0217 (8)	0.0080 (9)	−0.0158 (8)
C10	0.0752 (11)	0.0342 (7)	0.0583 (9)	0.0090 (7)	0.0007 (8)	−0.0044 (6)
C11	0.0564 (8)	0.0341 (6)	0.0432 (7)	−0.0043 (6)	0.0066 (6)	0.0020 (5)
C12	0.0406 (6)	0.0319 (6)	0.0315 (6)	0.0005 (5)	0.0079 (5)	0.0013 (4)
C13	0.0368 (7)	0.0510 (8)	0.0505 (8)	−0.0090 (6)	0.0172 (6)	−0.0151 (6)
C14	0.0345 (7)	0.0732 (10)	0.0499 (8)	−0.0107 (7)	0.0131 (6)	−0.0233 (7)
C15	0.0484 (9)	0.0934 (14)	0.0787 (12)	−0.0280 (9)	0.0260 (9)	−0.0347 (10)
C16	0.0436 (10)	0.144 (2)	0.1069 (18)	−0.0334 (13)	0.0318 (11)	−0.0466 (17)
C17	0.0351 (9)	0.155 (3)	0.1101 (19)	−0.0022 (13)	0.0174 (10)	−0.0376 (18)
C18	0.0427 (9)	0.1165 (17)	0.0735 (12)	0.0177 (10)	0.0055 (8)	−0.0151 (12)
C19	0.0348 (7)	0.0841 (12)	0.0422 (8)	0.0019 (7)	0.0050 (6)	−0.0116 (7)
C20	0.0441 (7)	0.0485 (8)	0.0344 (6)	0.0056 (6)	0.0126 (5)	0.0054 (5)
C21	0.0312 (6)	0.0437 (7)	0.0471 (7)	0.0024 (5)	0.0159 (5)	0.0019 (5)
C22	0.0566 (9)	0.0508 (8)	0.0516 (8)	0.0114 (7)	0.0253 (7)	0.0060 (6)
C23	0.0592 (10)	0.0708 (11)	0.0512 (9)	0.0109 (8)	0.0248 (8)	−0.0019 (8)
C24	0.0411 (8)	0.0614 (10)	0.0685 (10)	0.0054 (7)	0.0190 (7)	−0.0145 (8)
C25	0.0757 (12)	0.0464 (9)	0.0819 (13)	0.0145 (8)	0.0208 (10)	−0.0001 (8)
C26	0.0701 (11)	0.0485 (9)	0.0561 (9)	0.0107 (7)	0.0189 (8)	0.0069 (7)
C27	0.0697 (12)	0.0794 (14)	0.0981 (16)	0.0079 (10)	0.0307 (11)	−0.0328 (11)
N1	0.0348 (5)	0.0465 (6)	0.0364 (5)	−0.0024 (4)	0.0073 (4)	0.0027 (4)
N2	0.0459 (6)	0.0404 (6)	0.0509 (7)	−0.0014 (5)	0.0274 (5)	0.0064 (5)
O1	0.0583 (6)	0.0341 (5)	0.0744 (7)	0.0032 (4)	0.0344 (5)	0.0138 (5)
O2	0.0464 (6)	0.0712 (7)	0.0436 (5)	0.0159 (5)	0.0056 (4)	0.0086 (5)
O3	0.0682 (7)	0.0571 (7)	0.0645 (7)	0.0054 (5)	0.0314 (6)	0.0256 (5)

C1—N1	1.4577 (16)	C13—H13A	0.9700
C1—C12	1.5089 (17)	C13—H13B	0.9700
C1—C6	1.5621 (16)	C14—C19	1.370 (3)
C1—C2	1.5975 (17)	C14—C15	1.391 (2)
C2—C20	1.5240 (18)	C15—C16	1.383 (3)
C2—C13	1.5356 (18)	C15—H15	0.9300
C2—C3	1.5652 (17)	C16—C17	1.363 (4)
C3—C21	1.5110 (18)	C16—H16	0.9300
C3—C4	1.5169 (19)	C17—C18	1.380 (4)
C3—H3	0.9800	C17—H17	0.9300
C4—N1	1.4497 (18)	C18—C19	1.384 (2)
C4—H4A	0.9700	C18—H18	0.9300
C4—H4B	0.9700	C19—O2	1.396 (2)
C5—N1	1.4529 (18)	C20—O3	1.1892 (17)
C5—H5A	0.9600	C20—O2	1.3637 (17)
C5—H5B	0.9600	C21—C26	1.382 (2)
C5—H5C	0.9600	C21—C22	1.382 (2)
C6—O1	1.2243 (16)	C22—C23	1.383 (2)
C6—N2	1.3467 (17)	C22—H22	0.9300
C7—C8	1.3736 (19)	C23—C24	1.372 (2)
C7—C12	1.3857 (18)	C23—H23	0.9300
C7—N2	1.3964 (18)	C24—C25	1.375 (3)
C8—C9	1.381 (2)	C24—C27	1.505 (2)
C8—H8	0.9300	C25—C26	1.382 (2)
C9—C10	1.374 (3)	C25—H25	0.9300
C9—H9	0.9300	C26—H26	0.9300
C10—C11	1.387 (2)	C27—H27A	0.9600
C10—H10	0.9300	C27—H27B	0.9600
C11—C12	1.3820 (18)	C27—H27C	0.9600
C11—H11	0.9300	N2—H2	0.8600
C13—C14	1.496 (2)
N1—C1—C12	111.83 (10)	C2—C13—H13B	109.7
N1—C1—C6	113.05 (10)	H13A—C13—H13B	108.2
C12—C1—C6	100.52 (9)	C19—C14—C15	118.22 (16)
N1—C1—C2	102.96 (9)	C19—C14—C13	117.33 (14)
C12—C1—C2	117.43 (10)	C15—C14—C13	124.44 (17)
C6—C1—C2	111.50 (10)	C16—C15—C14	120.0 (2)
C20—C2—C13	106.66 (11)	C16—C15—H15	120.0
C20—C2—C3	110.37 (10)	C14—C15—H15	120.0
C13—C2—C3	112.93 (10)	C17—C16—C15	120.2 (2)
C20—C2—C1	108.58 (10)	C17—C16—H16	119.9
C13—C2—C1	114.63 (10)	C15—C16—H16	119.9
C3—C2—C1	103.64 (9)	C16—C17—C18	121.2 (2)
C21—C3—C4	116.52 (11)	C16—C17—H17	119.4
C21—C3—C2	115.59 (10)	C18—C17—H17	119.4
C4—C3—C2	103.51 (10)	C17—C18—C19	117.7 (2)
C21—C3—H3	106.9	C17—C18—H18	121.2
C4—C3—H3	106.9	C19—C18—H18	121.2
C2—C3—H3	106.9	C14—C19—C18	122.66 (18)
N1—C4—C3	102.26 (11)	C14—C19—O2	120.77 (13)
N1—C4—H4A	111.3	C18—C19—O2	116.53 (18)
C3—C4—H4A	111.3	O3—C20—O2	117.19 (13)
N1—C4—H4B	111.3	O3—C20—C2	125.69 (13)
C3—C4—H4B	111.3	O2—C20—C2	117.12 (12)
H4A—C4—H4B	109.2	C26—C21—C22	116.83 (14)
N1—C5—H5A	109.5	C26—C21—C3	122.78 (13)
N1—C5—H5B	109.5	C22—C21—C3	120.39 (12)
H5A—C5—H5B	109.5	C21—C22—C23	121.36 (15)
N1—C5—H5C	109.5	C21—C22—H22	119.3
H5A—C5—H5C	109.5	C23—C22—H22	119.3
H5B—C5—H5C	109.5	C24—C23—C22	121.72 (16)
O1—C6—N2	125.79 (12)	C24—C23—H23	119.1
O1—C6—C1	125.78 (11)	C22—C23—H23	119.1
N2—C6—C1	108.39 (11)	C23—C24—C25	117.01 (15)
C8—C7—C12	122.44 (13)	C23—C24—C27	122.04 (18)
C8—C7—N2	127.98 (13)	C25—C24—C27	120.95 (18)
C12—C7—N2	109.56 (11)	C24—C25—C26	121.77 (16)
C7—C8—C9	117.18 (16)	C24—C25—H25	119.1
C7—C8—H8	121.4	C26—C25—H25	119.1
C9—C8—H8	121.4	C21—C26—C25	121.29 (16)
C10—C9—C8	121.34 (15)	C21—C26—H26	119.4
C10—C9—H9	119.3	C25—C26—H26	119.4
C8—C9—H9	119.3	C24—C27—H27A	109.5
C9—C10—C11	121.08 (15)	C24—C27—H27B	109.5
C9—C10—H10	119.5	H27A—C27—H27B	109.5
C11—C10—H10	119.5	C24—C27—H27C	109.5
C12—C11—C10	118.15 (15)	H27A—C27—H27C	109.5
C12—C11—H11	120.9	H27B—C27—H27C	109.5
C10—C11—H11	120.9	C4—N1—C5	115.16 (11)
C11—C12—C7	119.70 (12)	C4—N1—C1	107.14 (10)
C11—C12—C1	130.64 (12)	C5—N1—C1	115.52 (11)
C7—C12—C1	109.60 (10)	C6—N2—C7	111.83 (11)
C14—C13—C2	109.89 (12)	C6—N2—H2	124.1
C14—C13—H13A	109.7	C7—N2—H2	124.1
C2—C13—H13A	109.7	C20—O2—C19	121.05 (12)
C14—C13—H13B	109.7
N1—C1—C2—C20	107.25 (11)	C13—C14—C15—C16	−179.46 (17)
C12—C1—C2—C20	−16.07 (14)	C14—C15—C16—C17	1.2 (3)
C6—C1—C2—C20	−131.25 (11)	C15—C16—C17—C18	−1.0 (4)
N1—C1—C2—C13	−133.62 (11)	C16—C17—C18—C19	0.2 (4)
C12—C1—C2—C13	103.06 (13)	C15—C14—C19—C18	−0.3 (2)
C6—C1—C2—C13	−12.12 (15)	C13—C14—C19—C18	178.73 (15)
N1—C1—C2—C3	−10.10 (11)	C15—C14—C19—O2	177.45 (14)
C12—C1—C2—C3	−133.42 (11)	C13—C14—C19—O2	−3.5 (2)
C6—C1—C2—C3	111.40 (11)	C17—C18—C19—C14	0.5 (3)
C20—C2—C3—C21	98.57 (13)	C17—C18—C19—O2	−177.40 (18)
C13—C2—C3—C21	−20.72 (15)	C13—C2—C20—O3	138.05 (15)
C1—C2—C3—C21	−145.34 (11)	C3—C2—C20—O3	15.04 (19)
C20—C2—C3—C4	−132.81 (11)	C1—C2—C20—O3	−97.92 (16)
C13—C2—C3—C4	107.91 (13)	C13—C2—C20—O2	−42.67 (15)
C1—C2—C3—C4	−16.72 (12)	C3—C2—C20—O2	−165.68 (11)
C21—C3—C4—N1	166.01 (10)	C1—C2—C20—O2	81.35 (14)
C2—C3—C4—N1	37.96 (13)	C4—C3—C21—C26	−22.73 (19)
N1—C1—C6—O1	55.83 (18)	C2—C3—C21—C26	99.17 (16)
C12—C1—C6—O1	175.18 (14)	C4—C3—C21—C22	156.91 (13)
C2—C1—C6—O1	−59.61 (18)	C2—C3—C21—C22	−81.19 (16)
N1—C1—C6—N2	−122.03 (12)	C26—C21—C22—C23	−0.4 (2)
C12—C1—C6—N2	−2.69 (13)	C3—C21—C22—C23	179.90 (14)
C2—C1—C6—N2	122.52 (12)	C21—C22—C23—C24	1.4 (3)
C12—C7—C8—C9	1.1 (2)	C22—C23—C24—C25	−1.0 (3)
N2—C7—C8—C9	−176.91 (14)	C22—C23—C24—C27	179.71 (17)
C7—C8—C9—C10	1.5 (2)	C23—C24—C25—C26	−0.4 (3)
C8—C9—C10—C11	−1.7 (3)	C27—C24—C25—C26	178.90 (18)
C9—C10—C11—C12	−0.7 (2)	C22—C21—C26—C25	−1.0 (2)
C10—C11—C12—C7	3.2 (2)	C3—C21—C26—C25	178.70 (15)
C10—C11—C12—C1	−179.77 (13)	C24—C25—C26—C21	1.4 (3)
C8—C7—C12—C11	−3.5 (2)	C3—C4—N1—C5	−177.27 (12)
N2—C7—C12—C11	174.86 (12)	C3—C4—N1—C1	−47.26 (13)
C8—C7—C12—C1	178.92 (13)	C12—C1—N1—C4	162.40 (10)
N2—C7—C12—C1	−2.76 (14)	C6—C1—N1—C4	−85.00 (12)
N1—C1—C12—C11	−53.82 (18)	C2—C1—N1—C4	35.44 (12)
C6—C1—C12—C11	−174.04 (13)	C12—C1—N1—C5	−67.79 (14)
C2—C1—C12—C11	64.87 (18)	C6—C1—N1—C5	44.80 (15)
N1—C1—C12—C7	123.46 (11)	C2—C1—N1—C5	165.25 (11)
C6—C1—C12—C7	3.23 (13)	O1—C6—N2—C7	−176.60 (14)
C2—C1—C12—C7	−117.86 (11)	C1—C6—N2—C7	1.27 (15)
C20—C2—C13—C14	57.15 (15)	C8—C7—N2—C6	179.11 (14)
C3—C2—C13—C14	178.55 (11)	C12—C7—N2—C6	0.90 (16)
C1—C2—C13—C14	−63.05 (16)	O3—C20—O2—C19	−176.49 (13)
C2—C13—C14—C19	−36.75 (18)	C2—C20—O2—C19	4.17 (18)
C2—C13—C14—C15	142.23 (15)	C14—C19—O2—C20	21.8 (2)
C19—C14—C15—C16	−0.5 (3)	C18—C19—O2—C20	−160.33 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.86	2.02	2.874 (1)	174.
C5—H5B···O3ii	0.96	2.59	3.407 (2)	143.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.86	2.02	2.874 (1)	174
C5—H5B⋯O3ii	0.96	2.59	3.407 (2)	143

Symmetry codes: (i) ; (ii) .