5-Amino-6-benzoyl-8-nitro-2,3-di-hydro-1H-spiro-[imidazo[1,2-a]pyridine-7,3'-indolin]-2'-one dimethyl sulfoxide monosolvate.

In the title compound C21H17N5O4·C2H6OS, the central six-membered ring derived from 1,4-di-hydro-pyridine adopts a distorted boat conformation with a small puckering amplitude of 0.127 (3) Å. The sums of bond angles around the pyridine N atom [358.7 (2)°] and the other imidazolidine N atom [60 (2)°] indicate that these atoms are in sp(2) hybridization, leading to an essentially planar imidazolidine ring. The last heterocycle, an oxindole moiety, is also nearly planar with an r.m.s. deviation of 0.0185 (1) Å. The amine NH2 group forms an intra-molecular hydrogen bond with the benzoyl group, giving a S(6) motif. In the crystal, N-H⋯O hydrogen bonds lead to the formation of chains along the c-axis direction. Within the chains there are further N-H⋯O and C-H⋯O hydrogen bonds enclosing R (2) 2(14) ring motifs. The chains are linked via N-H⋯O and C-H⋯O hydrogen bonds involving the dimethyl sulfoxide solvent mol-ecule which acts as both an acceptor and a donor..

Related literature

For a previous related work, see: Suresh et al. (2013 ▶). For conformational analysis of ring systems, and small rings fused to benzene, see: Cremer & Pople (1975 ▶); Allen (1981 ▶).

Experimental

Crystal data

C21H17N5O4·C2H6OS

M = 481.52

Monoclinic,

a = 16.476 (3) Å

b = 13.527 (2) Å

c = 10.0727 (18) Å

β = 99.868 (5)°

V = 2211.7 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 293 K

0.21 × 0.19 × 0.18 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.967, T max = 0.974

31940 measured reflections

4109 independent reflections

2818 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.160

S = 1.05

4109 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.92 e Å−3

Δρmin = −0.47 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814008800/bh2496sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008800/bh2496Isup2.hkl

CCDC reference: 998123

Additional supporting information: crystallographic information; 3D view; checkCIF report

C21H17N5O4·C2H6OS	F(000) = 1008
Mr = 481.52	Dx = 1.446 Mg m−3
Monoclinic, P21/c	Melting point: 530 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.476 (3) Å	Cell parameters from 2000 reflections
b = 13.527 (2) Å	θ = 2–31°
c = 10.0727 (18) Å	µ = 0.19 mm−1
β = 99.868 (5)°	T = 293 K
V = 2211.7 (7) Å3	Block, brown
Z = 4	0.21 × 0.19 × 0.18 mm

Bruker Kappa APEXII diffractometer	4109 independent reflections
Radiation source: fine-focus sealed tube	2818 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.070
Detector resolution: 0 pixels mm-1	θmax = 25.5°, θmin = 2.5°
ω and φ scans	h = −19→19
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −16→16
Tmin = 0.967, Tmax = 0.974	l = −12→12
31940 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0634P)2 + 2.4142P] where P = (Fo2 + 2Fc2)/3
4109 reflections	(Δ/σ)max < 0.001
307 parameters	Δρmax = 0.92 e Å−3
0 restraints	Δρmin = −0.47 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
C1	0.12735 (16)	0.47401 (19)	0.4943 (3)	0.0273 (6)
C2	0.19857 (15)	0.4409 (2)	0.6005 (3)	0.0268 (6)
C3	0.20085 (16)	0.3272 (2)	0.6119 (3)	0.0285 (6)
C4	0.14829 (16)	0.2694 (2)	0.5220 (3)	0.0292 (6)
C5	0.08157 (16)	0.4092 (2)	0.4049 (3)	0.0292 (6)
C6	−0.01200 (18)	0.3357 (2)	0.2370 (3)	0.0429 (8)
H6A	−0.0032	0.3343	0.1442	0.051*
H6B	−0.0705	0.3291	0.2384	0.051*
C7	0.03642 (18)	0.2551 (2)	0.3186 (3)	0.0432 (8)
H7A	0.0010	0.2147	0.3641	0.052*
H7B	0.0641	0.2132	0.2622	0.052*
C8	0.18947 (16)	0.4842 (2)	0.7405 (3)	0.0293 (6)
C9	0.30975 (16)	0.5444 (2)	0.6929 (3)	0.0330 (7)
C10	0.27937 (15)	0.4874 (2)	0.5812 (3)	0.0295 (6)
C11	0.32187 (17)	0.4803 (2)	0.4754 (3)	0.0371 (7)
H11	0.3022	0.4414	0.4006	0.045*
C12	0.39483 (19)	0.5327 (2)	0.4833 (4)	0.0473 (8)
H12	0.4244	0.5293	0.4127	0.057*
C13	0.42409 (19)	0.5898 (3)	0.5948 (4)	0.0494 (9)
H13	0.4731	0.6246	0.5978	0.059*
C14	0.38202 (18)	0.5964 (2)	0.7022 (4)	0.0434 (8)
H14	0.4019	0.6346	0.7775	0.052*
C15	0.2595 (3)	0.6930 (3)	0.2703 (4)	0.0615 (10)
H15A	0.3158	0.6979	0.3147	0.092*
H15B	0.2246	0.6827	0.3362	0.092*
H15C	0.2439	0.7531	0.2218	0.092*
C16	0.1423 (2)	0.6058 (3)	0.0959 (4)	0.0730 (12)
H16A	0.1245	0.5554	0.0302	0.109*
H16B	0.1319	0.6697	0.0550	0.109*
H16C	0.1126	0.5995	0.1695	0.109*
C31	0.25828 (18)	0.2769 (2)	0.7134 (3)	0.0362 (7)
C32	0.33727 (18)	0.3217 (2)	0.7853 (3)	0.0363 (7)
C33	0.4043 (2)	0.3233 (3)	0.7190 (4)	0.0495 (9)
H33	0.3980	0.3065	0.6283	0.059*
C34	0.4805 (2)	0.3501 (3)	0.7889 (5)	0.0672 (12)
H34	0.5259	0.3500	0.7453	0.081*
C35	0.4901 (3)	0.3769 (3)	0.9213 (5)	0.0768 (14)
H35	0.5418	0.3951	0.9672	0.092*
C36	0.4236 (3)	0.3768 (3)	0.9867 (4)	0.0719 (13)
H36	0.4299	0.3968	1.0763	0.086*
C37	0.3472 (2)	0.3471 (3)	0.9197 (3)	0.0519 (9)
H37	0.3027	0.3443	0.9651	0.062*
N1	0.10891 (14)	0.57350 (18)	0.4841 (2)	0.0330 (6)
N2	0.14345 (15)	0.17067 (18)	0.5281 (3)	0.0398 (6)
H2A	0.1097	0.1391	0.4684	0.048*
H2B	0.1741	0.1389	0.5917	0.048*
N3	0.25616 (14)	0.53850 (17)	0.7866 (2)	0.0342 (6)
H3	0.2651	0.5665	0.8644	0.041*
N4	0.09609 (13)	0.31051 (18)	0.4158 (2)	0.0326 (6)
N5	0.02048 (14)	0.42620 (19)	0.3037 (2)	0.0374 (6)
H5	0.0021	0.4842	0.2801	0.045*
O1	0.05174 (13)	0.60506 (16)	0.3938 (2)	0.0445 (6)
O2	0.14848 (13)	0.63220 (15)	0.5658 (2)	0.0431 (6)
O3	0.13161 (12)	0.46735 (14)	0.80020 (19)	0.0352 (5)
O4	0.24819 (17)	0.18945 (18)	0.7443 (3)	0.0682 (8)
O5	0.28997 (18)	0.6227 (3)	0.0417 (3)	0.0927 (12)
S1	0.24911 (7)	0.59246 (8)	0.15647 (10)	0.0650 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0223 (13)	0.0279 (15)	0.0298 (14)	0.0015 (11)	−0.0003 (11)	0.0011 (12)
C2	0.0203 (13)	0.0296 (14)	0.0287 (14)	−0.0009 (11)	−0.0009 (11)	−0.0003 (12)
C3	0.0221 (13)	0.0311 (15)	0.0312 (15)	−0.0011 (11)	0.0015 (11)	−0.0002 (12)
C4	0.0213 (13)	0.0322 (16)	0.0343 (15)	−0.0013 (11)	0.0048 (11)	−0.0007 (12)
C5	0.0209 (13)	0.0380 (17)	0.0283 (14)	0.0006 (11)	0.0034 (11)	0.0006 (12)
C6	0.0273 (16)	0.057 (2)	0.0399 (17)	0.0011 (14)	−0.0074 (13)	−0.0116 (15)
C7	0.0305 (16)	0.0461 (19)	0.0474 (19)	−0.0066 (14)	−0.0093 (14)	−0.0115 (15)
C8	0.0247 (14)	0.0260 (14)	0.0352 (15)	0.0037 (11)	−0.0007 (12)	0.0025 (12)
C9	0.0234 (14)	0.0331 (16)	0.0404 (16)	0.0002 (12)	−0.0006 (12)	−0.0012 (13)
C10	0.0192 (13)	0.0307 (15)	0.0366 (15)	0.0018 (11)	−0.0009 (11)	0.0020 (12)
C11	0.0277 (15)	0.0436 (18)	0.0385 (17)	0.0032 (13)	0.0015 (12)	0.0028 (14)
C12	0.0321 (17)	0.054 (2)	0.058 (2)	−0.0006 (15)	0.0134 (15)	0.0095 (17)
C13	0.0248 (16)	0.050 (2)	0.073 (2)	−0.0077 (14)	0.0066 (16)	0.0033 (18)
C14	0.0257 (15)	0.0425 (19)	0.058 (2)	−0.0073 (13)	−0.0031 (14)	−0.0093 (16)
C15	0.074 (3)	0.059 (2)	0.049 (2)	0.005 (2)	0.0023 (19)	−0.0067 (18)
C16	0.059 (3)	0.089 (3)	0.071 (3)	−0.006 (2)	0.012 (2)	−0.018 (2)
C31	0.0331 (16)	0.0346 (17)	0.0383 (17)	0.0008 (13)	−0.0012 (13)	0.0013 (13)
C32	0.0307 (16)	0.0320 (16)	0.0423 (17)	0.0042 (12)	−0.0049 (13)	0.0066 (13)
C33	0.0407 (19)	0.050 (2)	0.058 (2)	0.0070 (15)	0.0094 (16)	0.0066 (17)
C34	0.0297 (19)	0.068 (3)	0.103 (4)	0.0031 (18)	0.007 (2)	0.021 (2)
C35	0.042 (2)	0.081 (3)	0.095 (3)	−0.020 (2)	−0.024 (2)	0.028 (3)
C36	0.073 (3)	0.081 (3)	0.050 (2)	−0.023 (2)	−0.021 (2)	0.009 (2)
C37	0.047 (2)	0.064 (2)	0.0402 (19)	−0.0104 (17)	−0.0042 (15)	0.0026 (17)
N1	0.0254 (12)	0.0367 (14)	0.0352 (13)	0.0021 (10)	0.0006 (10)	0.0050 (11)
N2	0.0381 (14)	0.0295 (14)	0.0482 (15)	−0.0054 (11)	−0.0028 (12)	−0.0016 (11)
N3	0.0299 (13)	0.0379 (14)	0.0322 (13)	−0.0008 (10)	−0.0019 (10)	−0.0067 (11)
N4	0.0218 (12)	0.0362 (14)	0.0364 (13)	0.0002 (10)	−0.0045 (10)	−0.0058 (11)
N5	0.0274 (13)	0.0447 (15)	0.0355 (13)	0.0032 (11)	−0.0080 (10)	−0.0004 (12)
O1	0.0371 (12)	0.0430 (13)	0.0466 (13)	0.0088 (10)	−0.0117 (10)	0.0091 (10)
O2	0.0402 (12)	0.0334 (12)	0.0500 (13)	−0.0012 (9)	−0.0083 (10)	−0.0052 (10)
O3	0.0287 (11)	0.0408 (12)	0.0360 (11)	0.0024 (9)	0.0054 (9)	0.0033 (9)
O4	0.0734 (18)	0.0428 (15)	0.0733 (18)	−0.0118 (13)	−0.0298 (14)	0.0201 (13)
O5	0.0581 (18)	0.163 (3)	0.0610 (17)	−0.0245 (19)	0.0210 (14)	−0.053 (2)
S1	0.0735 (7)	0.0610 (7)	0.0544 (6)	0.0189 (5)	−0.0064 (5)	−0.0117 (5)

C1—N1	1.380 (4)	C13—H13	0.9300
C1—C5	1.384 (4)	C14—H14	0.9300
C1—C2	1.514 (3)	C15—S1	1.769 (4)
C2—C10	1.515 (4)	C15—H15A	0.9600
C2—C3	1.542 (4)	C15—H15B	0.9600
C2—C8	1.558 (4)	C15—H15C	0.9600
C3—C4	1.383 (4)	C16—S1	1.771 (4)
C3—C31	1.439 (4)	C16—H16A	0.9600
C4—N2	1.340 (4)	C16—H16B	0.9600
C4—N4	1.370 (3)	C16—H16C	0.9600
C5—N5	1.324 (3)	C31—O4	1.242 (4)
C5—N4	1.357 (4)	C31—C32	1.504 (4)
C6—N5	1.454 (4)	C32—C37	1.380 (5)
C6—C7	1.509 (4)	C32—C33	1.385 (4)
C6—H6A	0.9700	C33—C34	1.379 (5)
C6—H6B	0.9700	C33—H33	0.9300
C7—N4	1.468 (3)	C34—C35	1.364 (6)
C7—H7A	0.9700	C34—H34	0.9300
C7—H7B	0.9700	C35—C36	1.372 (6)
C8—O3	1.232 (3)	C35—H35	0.9300
C8—N3	1.337 (4)	C36—C37	1.382 (5)
C9—C14	1.373 (4)	C36—H36	0.9300
C9—C10	1.385 (4)	C37—H37	0.9300
C9—N3	1.401 (4)	N1—O2	1.245 (3)
C10—C11	1.375 (4)	N1—O1	1.266 (3)
C11—C12	1.386 (4)	N2—H2A	0.8600
C11—H11	0.9300	N2—H2B	0.8600
C12—C13	1.380 (5)	N3—H3	0.8600
C12—H12	0.9300	N5—H5	0.8600
C13—C14	1.384 (5)	O5—S1	1.491 (3)
N1—C1—C5	118.8 (2)	S1—C15—H15A	109.5
N1—C1—C2	118.4 (2)	S1—C15—H15B	109.5
C5—C1—C2	122.8 (2)	H15A—C15—H15B	109.5
C1—C2—C10	112.2 (2)	S1—C15—H15C	109.5
C1—C2—C3	110.7 (2)	H15A—C15—H15C	109.5
C10—C2—C3	114.4 (2)	H15B—C15—H15C	109.5
C1—C2—C8	110.2 (2)	S1—C16—H16A	109.5
C10—C2—C8	100.5 (2)	S1—C16—H16B	109.5
C3—C2—C8	108.2 (2)	H16A—C16—H16B	109.5
C4—C3—C31	117.4 (3)	S1—C16—H16C	109.5
C4—C3—C2	120.7 (2)	H16A—C16—H16C	109.5
C31—C3—C2	121.9 (2)	H16B—C16—H16C	109.5
N2—C4—N4	114.0 (2)	O4—C31—C3	121.9 (3)
N2—C4—C3	124.7 (3)	O4—C31—C32	113.9 (3)
N4—C4—C3	121.4 (2)	C3—C31—C32	124.1 (3)
N5—C5—N4	109.5 (2)	C37—C32—C33	119.9 (3)
N5—C5—C1	130.4 (3)	C37—C32—C31	121.4 (3)
N4—C5—C1	120.1 (2)	C33—C32—C31	118.1 (3)
N5—C6—C7	103.8 (2)	C34—C33—C32	119.3 (4)
N5—C6—H6A	111.0	C34—C33—H33	120.3
C7—C6—H6A	111.0	C32—C33—H33	120.3
N5—C6—H6B	111.0	C35—C34—C33	120.8 (4)
C7—C6—H6B	111.0	C35—C34—H34	119.6
H6A—C6—H6B	109.0	C33—C34—H34	119.6
N4—C7—C6	103.1 (2)	C34—C35—C36	120.1 (4)
N4—C7—H7A	111.2	C34—C35—H35	120.0
C6—C7—H7A	111.2	C36—C35—H35	120.0
N4—C7—H7B	111.2	C35—C36—C37	120.1 (4)
C6—C7—H7B	111.2	C35—C36—H36	120.0
H7A—C7—H7B	109.1	C37—C36—H36	120.0
O3—C8—N3	126.2 (3)	C32—C37—C36	119.8 (4)
O3—C8—C2	125.1 (2)	C32—C37—H37	120.1
N3—C8—C2	108.7 (2)	C36—C37—H37	120.1
C14—C9—C10	121.9 (3)	O2—N1—O1	120.1 (2)
C14—C9—N3	128.6 (3)	O2—N1—C1	119.3 (2)
C10—C9—N3	109.5 (2)	O1—N1—C1	120.6 (2)
C11—C10—C9	120.5 (3)	C4—N2—H2A	120.0
C11—C10—C2	130.2 (3)	C4—N2—H2B	120.0
C9—C10—C2	109.3 (2)	H2A—N2—H2B	120.0
C10—C11—C12	118.1 (3)	C8—N3—C9	111.9 (2)
C10—C11—H11	120.9	C8—N3—H3	124.1
C12—C11—H11	120.9	C9—N3—H3	124.1
C13—C12—C11	120.8 (3)	C5—N4—C4	122.7 (2)
C13—C12—H12	119.6	C5—N4—C7	111.1 (2)
C11—C12—H12	119.6	C4—N4—C7	124.9 (2)
C12—C13—C14	121.3 (3)	C5—N5—C6	112.4 (2)
C12—C13—H13	119.3	C5—N5—H5	123.8
C14—C13—H13	119.3	C6—N5—H5	123.8
C9—C14—C13	117.3 (3)	O5—S1—C15	106.5 (2)
C9—C14—H14	121.3	O5—S1—C16	105.0 (2)
C13—C14—H14	121.3	C15—S1—C16	97.2 (2)
N1—C1—C2—C10	−60.0 (3)	C10—C9—C14—C13	−0.1 (5)
C5—C1—C2—C10	118.2 (3)	N3—C9—C14—C13	179.9 (3)
N1—C1—C2—C3	170.8 (2)	C12—C13—C14—C9	−0.4 (5)
C5—C1—C2—C3	−10.9 (4)	C4—C3—C31—O4	−18.9 (5)
N1—C1—C2—C8	51.1 (3)	C2—C3—C31—O4	162.4 (3)
C5—C1—C2—C8	−130.6 (3)	C4—C3—C31—C32	157.3 (3)
C1—C2—C3—C4	6.8 (4)	C2—C3—C31—C32	−21.4 (4)
C10—C2—C3—C4	−121.2 (3)	O4—C31—C32—C37	−73.6 (4)
C8—C2—C3—C4	127.7 (3)	C3—C31—C32—C37	109.9 (4)
C1—C2—C3—C31	−174.6 (2)	O4—C31—C32—C33	96.9 (4)
C10—C2—C3—C31	57.4 (3)	C3—C31—C32—C33	−79.6 (4)
C8—C2—C3—C31	−53.7 (3)	C37—C32—C33—C34	0.2 (5)
C31—C3—C4—N2	4.5 (4)	C31—C32—C33—C34	−170.4 (3)
C2—C3—C4—N2	−176.8 (3)	C32—C33—C34—C35	−1.3 (6)
C31—C3—C4—N4	−174.9 (3)	C33—C34—C35—C36	0.3 (6)
C2—C3—C4—N4	3.8 (4)	C34—C35—C36—C37	1.8 (7)
N1—C1—C5—N5	1.4 (5)	C33—C32—C37—C36	1.9 (5)
C2—C1—C5—N5	−176.8 (3)	C31—C32—C37—C36	172.2 (3)
N1—C1—C5—N4	−177.4 (2)	C35—C36—C37—C32	−2.8 (6)
C2—C1—C5—N4	4.4 (4)	C5—C1—N1—O2	178.4 (2)
N5—C6—C7—N4	−4.7 (3)	C2—C1—N1—O2	−3.3 (4)
C1—C2—C8—O3	61.2 (3)	C5—C1—N1—O1	−0.7 (4)
C10—C2—C8—O3	179.8 (3)	C2—C1—N1—O1	177.6 (2)
C3—C2—C8—O3	−60.0 (3)	O3—C8—N3—C9	−179.0 (3)
C1—C2—C8—N3	−121.4 (2)	C2—C8—N3—C9	3.6 (3)
C10—C2—C8—N3	−2.8 (3)	C14—C9—N3—C8	177.1 (3)
C3—C2—C8—N3	117.4 (2)	C10—C9—N3—C8	−2.9 (3)
C14—C9—C10—C11	0.8 (4)	N5—C5—N4—C4	−171.2 (2)
N3—C9—C10—C11	−179.2 (2)	C1—C5—N4—C4	7.8 (4)
C14—C9—C10—C2	−179.2 (3)	N5—C5—N4—C7	−3.7 (3)
N3—C9—C10—C2	0.9 (3)	C1—C5—N4—C7	175.3 (3)
C1—C2—C10—C11	−61.7 (4)	N2—C4—N4—C5	168.5 (3)
C3—C2—C10—C11	65.5 (4)	C3—C4—N4—C5	−12.0 (4)
C8—C2—C10—C11	−178.8 (3)	N2—C4—N4—C7	2.8 (4)
C1—C2—C10—C9	118.2 (3)	C3—C4—N4—C7	−177.8 (3)
C3—C2—C10—C9	−114.6 (3)	C6—C7—N4—C5	5.3 (3)
C8—C2—C10—C9	1.1 (3)	C6—C7—N4—C4	172.5 (3)
C9—C10—C11—C12	−0.9 (4)	N4—C5—N5—C6	0.3 (3)
C2—C10—C11—C12	179.0 (3)	C1—C5—N5—C6	−178.6 (3)
C10—C11—C12—C13	0.4 (5)	C7—C6—N5—C5	3.0 (3)
C11—C12—C13—C14	0.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O4	0.86	1.92	2.549 (3)	129
N2—H2A···O3i	0.86	2.30	2.939 (3)	131
N3—H3···O5ii	0.86	1.92	2.779 (4)	177
N5—H5···O1	0.86	2.08	2.604 (3)	119
N5—H5···O3iii	0.86	2.31	2.924 (3)	129
C6—H6B···O2iii	0.97	2.59	3.274 (4)	128
C11—H11···O4i	0.93	2.43	3.346 (4)	167
C15—H15C···O2iv	0.96	2.55	3.448 (4)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O4	0.86	1.92	2.549 (3)	129
N2—H2A⋯O3i	0.86	2.30	2.939 (3)	131
N3—H3⋯O5ii	0.86	1.92	2.779 (4)	177
N5—H5⋯O3iii	0.86	2.31	2.924 (3)	129
C6—H6B⋯O2iii	0.97	2.59	3.274 (4)	128
C11—H11⋯O4i	0.93	2.43	3.346 (4)	167
C15—H15C⋯O2iv	0.96	2.55	3.448 (4)	156

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .