5-Amino-5'-bromo-6-(4-methyl-benzo-yl)-8-nitro-2,3-di-hydro-1H-spiro-[imidazo[1,2-a]pyridine-7,3'-indolin]-2'-one including an unknown solvate.

In the title compound, C22H18BrN5O4, the central six-membered ring, derived from 1,4-di-hydro-pyridine, adopts a distorted boat conformation with a puckering amplitude of 0.197 (3) Å, the imidazole ring adopts a twisted conformation with a puckering amplitude of 0.113 (3) Å, and the oxindole moiety is planar with an r.m.s. deviation of 0.0125 Å. Two intra-molecular N-H⋯O hydrogen bonds are formed, each closing an S(6) loop. In the crystal, strong N-H⋯O hydrogen bonds lead to the formation of zigzag chains along the c axis. These are consolidated in the three-dimensional crystal packing by weak N-H⋯O hydrogen bonding, as well as by C-H⋯O, C-H⋯Br and C-H⋯π inter-actions. A small region of electron density well removed from the main mol-ecule was removed with the SQUEEZE procedure in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148-155] following unsuccessful attempts to model it as a plausible solvent mol-ecule. The unit-cell characteristics do not take into account this feature of the structure.

Related literature

For a similar structure, see: Nagalakshmi et al. (2014 ▶). For additional conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C22H18BrN5O4

M = 496.32

Monoclinic,

a = 15.5482 (9) Å

b = 14.7033 (7) Å

c = 12.1907 (6) Å

β = 101.856 (2)°

V = 2727.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 1.54 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

30073 measured reflections

5962 independent reflections

4098 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.114

S = 1.04

5962 reflections

289 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.41 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/S1600536814014391/tk5316sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014391/tk5316Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814014391/tk5316Isup3.cml

CCDC reference: 1009067

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

C22H18BrN5O4	F(000) = 1008
Mr = 496.32	Dx = 1.209 Mg m−3
Monoclinic, P21/c	Melting point: 530 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.5482 (9) Å	Cell parameters from 2000 reflections
b = 14.7033 (7) Å	θ = 2–31°
c = 12.1907 (6) Å	µ = 1.54 mm−1
β = 101.856 (2)°	T = 293 K
V = 2727.5 (2) Å3	Block, brown
Z = 4	0.21 × 0.19 × 0.18 mm

Bruker Kappa APEXII diffractometer	5962 independent reflections
Radiation source: fine-focus sealed tube	4098 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 0 pixels mm-1	θmax = 27.0°, θmin = 1.9°
ω and φ scans	h = −19→11
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −18→18
Tmin = 0.967, Tmax = 0.974	l = −15→15
30073 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0653P)2] where P = (Fo2 + 2Fc2)/3
5962 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.30 e Å−3
1 restraint	Δρmin = −0.41 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	0.10831 (12)	−0.03982 (13)	0.29919 (16)	0.0302 (4)
C2	0.16209 (12)	0.04483 (12)	0.33939 (15)	0.0273 (4)
C3	0.15943 (12)	0.06548 (13)	0.46280 (15)	0.0302 (4)
C4	0.13013 (12)	−0.00186 (13)	0.52880 (16)	0.0335 (4)
C5	0.08565 (12)	−0.10239 (13)	0.37313 (16)	0.0315 (4)
C6	0.04187 (16)	−0.22940 (16)	0.45722 (19)	0.0509 (6)
H6A	0.0818	−0.2808	0.4694	0.061*
H6B	−0.0174	−0.2508	0.4555	0.061*
C7	0.06850 (15)	−0.15800 (14)	0.54656 (19)	0.0421 (5)
H7A	0.0184	−0.1374	0.5759	0.051*
H7B	0.1133	−0.1808	0.6078	0.051*
C8	0.12622 (12)	0.12869 (13)	0.26493 (15)	0.0305 (4)
C9	0.26599 (13)	0.10750 (13)	0.24292 (16)	0.0327 (4)
C10	0.25462 (12)	0.03862 (12)	0.31650 (15)	0.0291 (4)
C11	0.32166 (12)	−0.02155 (14)	0.35672 (16)	0.0363 (5)
H11	0.3146	−0.0680	0.4059	0.044*
C12	0.39967 (14)	−0.01014 (17)	0.32108 (19)	0.0461 (5)
C13	0.41184 (14)	0.05743 (17)	0.2473 (2)	0.0498 (6)
H13	0.4653	0.0626	0.2250	0.060*
C14	0.34405 (14)	0.11796 (16)	0.20630 (18)	0.0449 (5)
H14	0.3509	0.1637	0.1562	0.054*
C31	0.18598 (14)	0.15050 (13)	0.51348 (17)	0.0376 (5)
C32	0.23171 (13)	0.22376 (13)	0.46127 (16)	0.0346 (4)
C33	0.31931 (14)	0.21652 (15)	0.45811 (19)	0.0452 (5)
H33	0.3489	0.1621	0.4781	0.054*
C34	0.36363 (16)	0.29024 (19)	0.4251 (2)	0.0608 (6)
H34	0.4228	0.2845	0.4230	0.073*
C35	0.3216 (2)	0.37187 (19)	0.3955 (2)	0.0621 (7)
C36	0.23388 (18)	0.37875 (16)	0.3996 (2)	0.0515 (6)
H36	0.2043	0.4332	0.3798	0.062*
C37	0.18933 (14)	0.30590 (14)	0.43283 (16)	0.0381 (5)
H37	0.1304	0.3120	0.4361	0.046*
C38	0.3699 (3)	0.4543 (3)	0.3619 (4)	0.1206 (16)
H38A	0.3299	0.5046	0.3458	0.181*
H38B	0.3926	0.4399	0.2965	0.181*
H38C	0.4175	0.4703	0.4223	0.181*
N1	0.09080 (11)	−0.06034 (12)	0.18652 (14)	0.0389 (4)
N2	0.12708 (14)	0.00993 (13)	0.63557 (15)	0.0548 (5)
H2A	0.1089	−0.0333	0.6725	0.066*
H2B	0.1433	0.0608	0.6680	0.066*
N3	0.19037 (10)	0.16040 (11)	0.21672 (13)	0.0336 (4)
H3	0.1854	0.2078	0.1746	0.040*
N4	0.10306 (11)	−0.08480 (10)	0.48544 (13)	0.0342 (4)
N5	0.04712 (11)	−0.18207 (12)	0.35518 (15)	0.0412 (4)
H5	0.0271	−0.2038	0.2894	0.049*
O1	0.05241 (12)	−0.13281 (11)	0.15117 (13)	0.0546 (4)
O2	0.11477 (11)	−0.00570 (11)	0.12016 (12)	0.0494 (4)
O3	0.05189 (9)	0.15950 (10)	0.25570 (12)	0.0413 (4)
O4	0.17505 (15)	0.17071 (11)	0.60983 (14)	0.0669 (5)
Br1	0.493532 (17)	−0.09216 (2)	0.37527 (3)	0.07818 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0390 (9)	0.0255 (10)	0.0254 (10)	0.0006 (7)	0.0052 (8)	−0.0020 (8)
C2	0.0378 (9)	0.0216 (10)	0.0219 (9)	0.0030 (7)	0.0048 (7)	0.0008 (8)
C3	0.0428 (10)	0.0230 (10)	0.0243 (10)	0.0030 (8)	0.0058 (8)	0.0009 (8)
C4	0.0427 (10)	0.0283 (11)	0.0290 (11)	0.0032 (8)	0.0059 (8)	0.0012 (9)
C5	0.0351 (9)	0.0254 (10)	0.0332 (11)	0.0012 (7)	0.0052 (8)	−0.0028 (8)
C6	0.0645 (14)	0.0402 (14)	0.0485 (14)	−0.0178 (11)	0.0124 (11)	0.0030 (11)
C7	0.0533 (12)	0.0334 (12)	0.0411 (13)	−0.0091 (9)	0.0131 (10)	0.0072 (10)
C8	0.0410 (10)	0.0241 (10)	0.0244 (10)	0.0048 (8)	0.0018 (8)	−0.0007 (8)
C9	0.0429 (10)	0.0282 (11)	0.0260 (10)	0.0008 (8)	0.0050 (8)	−0.0006 (8)
C10	0.0376 (9)	0.0250 (10)	0.0245 (10)	0.0007 (7)	0.0057 (8)	−0.0035 (8)
C11	0.0410 (10)	0.0352 (12)	0.0306 (11)	0.0053 (8)	0.0021 (8)	0.0019 (9)
C12	0.0408 (11)	0.0527 (14)	0.0421 (13)	0.0134 (10)	0.0028 (9)	−0.0025 (11)
C13	0.0406 (11)	0.0635 (16)	0.0485 (14)	−0.0003 (11)	0.0164 (10)	−0.0020 (12)
C14	0.0511 (12)	0.0486 (14)	0.0379 (13)	−0.0054 (10)	0.0161 (10)	0.0047 (11)
C31	0.0577 (12)	0.0270 (11)	0.0279 (11)	0.0004 (9)	0.0080 (9)	−0.0012 (9)
C32	0.0497 (11)	0.0251 (11)	0.0261 (10)	−0.0015 (8)	0.0012 (8)	−0.0048 (8)
C33	0.0483 (11)	0.0365 (13)	0.0472 (13)	0.0031 (9)	0.0014 (10)	−0.0099 (10)
C34	0.0533 (13)	0.0669 (15)	0.0663 (17)	−0.0117 (11)	0.0217 (12)	−0.0200 (13)
C35	0.0841 (18)	0.0504 (13)	0.0619 (17)	−0.0197 (11)	0.0385 (14)	−0.0100 (12)
C36	0.0818 (17)	0.0306 (12)	0.0455 (14)	0.0039 (11)	0.0211 (12)	0.0050 (10)
C37	0.0485 (11)	0.0317 (12)	0.0349 (12)	0.0026 (9)	0.0105 (9)	−0.0019 (9)
C38	0.143 (4)	0.081 (3)	0.164 (4)	−0.046 (2)	0.093 (3)	0.000 (3)
N1	0.0517 (10)	0.0333 (10)	0.0308 (10)	−0.0021 (8)	0.0061 (8)	−0.0050 (8)
N2	0.1040 (16)	0.0329 (11)	0.0321 (11)	−0.0126 (10)	0.0243 (10)	−0.0022 (8)
N3	0.0464 (9)	0.0267 (9)	0.0267 (9)	0.0032 (7)	0.0049 (7)	0.0074 (7)
N4	0.0481 (9)	0.0259 (9)	0.0284 (9)	−0.0050 (7)	0.0074 (7)	0.0020 (7)
N5	0.0548 (10)	0.0327 (10)	0.0348 (10)	−0.0114 (8)	0.0060 (8)	−0.0036 (8)
O1	0.0814 (11)	0.0412 (9)	0.0393 (9)	−0.0214 (8)	0.0080 (8)	−0.0155 (7)
O2	0.0767 (11)	0.0408 (9)	0.0305 (8)	−0.0099 (8)	0.0104 (7)	−0.0016 (7)
O3	0.0428 (7)	0.0396 (9)	0.0387 (9)	0.0142 (6)	0.0021 (6)	0.0049 (6)
O4	0.1371 (17)	0.0322 (9)	0.0391 (10)	−0.0172 (10)	0.0359 (10)	−0.0120 (7)
Br1	0.05198 (16)	0.0981 (3)	0.0821 (3)	0.03710 (14)	0.00837 (14)	0.01124 (17)

C1—N1	1.378 (3)	C12—C13	1.379 (3)
C1—C5	1.383 (3)	C12—Br1	1.904 (2)
C1—C2	1.523 (3)	C13—C14	1.392 (3)
C2—C10	1.523 (2)	C13—H13	0.9300
C2—C3	1.544 (3)	C14—H14	0.9300
C2—C8	1.564 (3)	C31—O4	1.257 (2)
C3—C4	1.409 (3)	C31—C32	1.502 (3)
C3—C31	1.418 (3)	C32—C33	1.374 (3)
C4—N2	1.324 (3)	C32—C37	1.385 (3)
C4—N4	1.361 (3)	C33—C34	1.388 (3)
C5—N5	1.314 (2)	C33—H33	0.9300
C5—N4	1.365 (3)	C34—C35	1.379 (4)
C6—N5	1.442 (3)	C34—H34	0.9300
C6—C7	1.508 (3)	C35—C36	1.379 (4)
C6—H6A	0.9700	C35—C38	1.525 (4)
C6—H6B	0.9700	C36—C37	1.381 (3)
C7—N4	1.472 (2)	C36—H36	0.9300
C7—H7A	0.9700	C37—H37	0.9300
C7—H7B	0.9700	C38—H38A	0.9600
C8—O3	1.225 (2)	C38—H38B	0.9600
C8—N3	1.341 (2)	C38—H38C	0.9600
C9—C14	1.385 (3)	N1—O2	1.250 (2)
C9—C10	1.388 (3)	N1—O1	1.254 (2)
C9—N3	1.391 (2)	N2—H2A	0.8600
C10—C11	1.378 (3)	N2—H2B	0.8600
C11—C12	1.380 (3)	N3—H3	0.8600
C11—H11	0.9300	N5—H5	0.8600
N1—C1—C5	118.64 (17)	C14—C13—H13	120.0
N1—C1—C2	118.86 (16)	C9—C14—C13	117.5 (2)
C5—C1—C2	122.03 (16)	C9—C14—H14	121.2
C1—C2—C10	111.65 (14)	C13—C14—H14	121.2
C1—C2—C3	110.57 (14)	O4—C31—C3	122.18 (18)
C10—C2—C3	113.94 (15)	O4—C31—C32	113.15 (17)
C1—C2—C8	110.53 (15)	C3—C31—C32	124.64 (17)
C10—C2—C8	100.28 (14)	C33—C32—C37	118.93 (19)
C3—C2—C8	109.43 (14)	C33—C32—C31	120.95 (19)
C4—C3—C31	118.04 (17)	C37—C32—C31	119.27 (18)
C4—C3—C2	119.66 (16)	C32—C33—C34	120.1 (2)
C31—C3—C2	122.30 (16)	C32—C33—H33	120.0
N2—C4—N4	115.38 (18)	C34—C33—H33	120.0
N2—C4—C3	123.41 (19)	C35—C34—C33	121.3 (2)
N4—C4—C3	121.21 (17)	C35—C34—H34	119.4
N5—C5—N4	109.02 (17)	C33—C34—H34	119.4
N5—C5—C1	130.78 (18)	C36—C35—C34	118.3 (2)
N4—C5—C1	120.20 (17)	C36—C35—C38	119.8 (3)
N5—C6—C7	103.37 (16)	C34—C35—C38	121.9 (3)
N5—C6—H6A	111.1	C35—C36—C37	120.9 (2)
C7—C6—H6A	111.1	C35—C36—H36	119.6
N5—C6—H6B	111.1	C37—C36—H36	119.6
C7—C6—H6B	111.1	C36—C37—C32	120.5 (2)
H6A—C6—H6B	109.1	C36—C37—H37	119.7
N4—C7—C6	102.60 (16)	C32—C37—H37	119.7
N4—C7—H7A	111.2	C35—C38—H38A	109.5
C6—C7—H7A	111.2	C35—C38—H38B	109.5
N4—C7—H7B	111.2	H38A—C38—H38B	109.5
C6—C7—H7B	111.2	C35—C38—H38C	109.5
H7A—C7—H7B	109.2	H38A—C38—H38C	109.5
O3—C8—N3	127.15 (18)	H38B—C38—H38C	109.5
O3—C8—C2	124.20 (17)	O2—N1—O1	120.52 (17)
N3—C8—C2	108.65 (15)	O2—N1—C1	118.71 (16)
C14—C9—C10	121.71 (18)	O1—N1—C1	120.76 (17)
C14—C9—N3	128.25 (18)	C4—N2—H2A	120.0
C10—C9—N3	110.03 (16)	C4—N2—H2B	120.0
C11—C10—C9	120.72 (17)	H2A—N2—H2B	120.0
C11—C10—C2	130.31 (17)	C8—N3—C9	112.00 (15)
C9—C10—C2	108.97 (15)	C8—N3—H3	124.0
C10—C11—C12	117.34 (19)	C9—N3—H3	124.0
C10—C11—H11	121.3	C4—N4—C5	122.77 (16)
C12—C11—H11	121.3	C4—N4—C7	125.06 (17)
C13—C12—C11	122.7 (2)	C5—N4—C7	110.57 (16)
C13—C12—Br1	118.99 (16)	C5—N5—C6	113.04 (17)
C11—C12—Br1	118.32 (17)	C5—N5—H5	123.5
C12—C13—C14	119.99 (19)	C6—N5—H5	123.5
C12—C13—H13	120.0
N1—C1—C2—C10	−62.7 (2)	C10—C9—C14—C13	−0.9 (3)
C5—C1—C2—C10	109.30 (19)	N3—C9—C14—C13	178.1 (2)
N1—C1—C2—C3	169.32 (16)	C12—C13—C14—C9	0.4 (3)
C5—C1—C2—C3	−18.7 (2)	C4—C3—C31—O4	−8.1 (3)
N1—C1—C2—C8	48.0 (2)	C2—C3—C31—O4	172.2 (2)
C5—C1—C2—C8	−139.99 (18)	C4—C3—C31—C32	169.99 (18)
C1—C2—C3—C4	15.3 (2)	C2—C3—C31—C32	−9.7 (3)
C10—C2—C3—C4	−111.41 (19)	O4—C31—C32—C33	102.3 (2)
C8—C2—C3—C4	137.27 (17)	C3—C31—C32—C33	−75.9 (3)
C1—C2—C3—C31	−164.99 (17)	O4—C31—C32—C37	−67.0 (3)
C10—C2—C3—C31	68.3 (2)	C3—C31—C32—C37	114.8 (2)
C8—C2—C3—C31	−43.0 (2)	C37—C32—C33—C34	−1.0 (3)
C31—C3—C4—N2	−0.7 (3)	C31—C32—C33—C34	−170.3 (2)
C2—C3—C4—N2	178.98 (19)	C32—C33—C34—C35	0.3 (4)
C31—C3—C4—N4	179.52 (18)	C33—C34—C35—C36	0.2 (4)
C2—C3—C4—N4	−0.8 (3)	C33—C34—C35—C38	178.4 (3)
N1—C1—C5—N5	−1.1 (3)	C34—C35—C36—C37	0.1 (4)
C2—C1—C5—N5	−173.18 (19)	C38—C35—C36—C37	−178.1 (3)
N1—C1—C5—N4	179.15 (16)	C35—C36—C37—C32	−0.9 (3)
C2—C1—C5—N4	7.1 (3)	C33—C32—C37—C36	1.3 (3)
N5—C6—C7—N4	−11.3 (2)	C31—C32—C37—C36	170.8 (2)
C1—C2—C8—O3	61.5 (2)	C5—C1—N1—O2	−176.85 (18)
C10—C2—C8—O3	179.41 (18)	C2—C1—N1—O2	−4.6 (3)
C3—C2—C8—O3	−60.5 (2)	C5—C1—N1—O1	2.4 (3)
C1—C2—C8—N3	−119.69 (16)	C2—C1—N1—O1	174.70 (17)
C10—C2—C8—N3	−1.77 (19)	O3—C8—N3—C9	−178.42 (19)
C3—C2—C8—N3	118.31 (16)	C2—C8—N3—C9	2.8 (2)
C14—C9—C10—C11	0.7 (3)	C14—C9—N3—C8	178.2 (2)
N3—C9—C10—C11	−178.48 (17)	C10—C9—N3—C8	−2.7 (2)
C14—C9—C10—C2	−179.42 (18)	N2—C4—N4—C5	166.80 (18)
N3—C9—C10—C2	1.4 (2)	C3—C4—N4—C5	−13.5 (3)
C1—C2—C10—C11	−62.8 (3)	N2—C4—N4—C7	2.6 (3)
C3—C2—C10—C11	63.3 (3)	C3—C4—N4—C7	−177.68 (18)
C8—C2—C10—C11	−179.93 (19)	N5—C5—N4—C4	−169.47 (17)
C1—C2—C10—C9	117.27 (17)	C1—C5—N4—C4	10.3 (3)
C3—C2—C10—C9	−116.59 (17)	N5—C5—N4—C7	−3.2 (2)
C8—C2—C10—C9	0.18 (19)	C1—C5—N4—C7	176.55 (17)
C9—C10—C11—C12	0.1 (3)	C6—C7—N4—C4	175.24 (19)
C2—C10—C11—C12	−179.74 (19)	C6—C7—N4—C5	9.4 (2)
C10—C11—C12—C13	−0.7 (3)	N4—C5—N5—C6	−5.0 (2)
C10—C11—C12—Br1	179.96 (14)	C1—C5—N5—C6	175.2 (2)
C11—C12—C13—C14	0.4 (4)	C7—C6—N5—C5	10.7 (2)
Br1—C12—C13—C14	179.77 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O1	0.86	2.09	2.608 (2)	118
N2—H2B···O4	0.86	1.87	2.518 (2)	131
N3—H3···O4i	0.86	1.95	2.792 (2)	168
N5—H5···O3ii	0.86	2.36	2.961 (2)	127
C7—H7A···O3iii	0.97	2.54	3.342 (3)	140
C33—H33···Br1iv	0.93	2.91	3.675 (2)	141
C14—H14···Cg1i	0.93	2.83	3.553 (2)	135

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C32–C37 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5⋯O1	0.86	2.09	2.608 (2)	118
N2—H2B⋯O4	0.86	1.87	2.518 (2)	131
N3—H3⋯O4i	0.86	1.95	2.792 (2)	168
N5—H5⋯O3ii	0.86	2.36	2.961 (2)	127
C7—H7A⋯O3iii	0.97	2.54	3.342 (3)	140
C33—H33⋯Br1iv	0.93	2.91	3.675 (2)	141
C14—H14⋯Cg1i	0.93	2.83	3.553 (2)	135

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