4-Phenyl-sulfon-yl-2-(p-tolyl-sulfon-yl)-1H,8H-pyrrolo-[2,3-b]indole.

The title compound, C(23)H(18)N(2)O(4)S(2), contains a pyrrolo group fused onto the plane of an indole ring with phenyl-sulfonyl and p-toluene-sulfonyl groups bonded to the indole and pyrrolo rings. The angles between the mean planes of the pyrrolo-indole ring and the phenyl-sulfonyl and p-toluene-sulfonyl rings are 73.7 (6) and 80.6 (0)°, respectively. The dihedral angle between the mean planes of the two benzene rings is 78.7 (4)°. In the crystal, both classical N-H⋯O and non-classical C-H⋯O inter-molecular hydrogen-bonding inter-actions are observed, as well as weak π-π inter-actions [centroid-centroid distances = 3.6258 (8) and 3.9298 (8) Å], which contribute to the stability of the packing.

Related literature

We have been inter­ested in the synthesis of fused indole heterocycles (Gribble et al., 2005 ▶) for the construction of more elaborate mol­ecules, such as the potent anti­biotics pyrroindomycins A and B (Abbanat et al., 1999 ▶; Ding et al., 1994 ▶) Both pyrrolo­[2,3-b]indoles and pyrrolo­[3,4-b]indoles can be synthesized in one step via the Barton–Zard pyrrole synthesis (Barton & Zard, 1985 ▶; Barton et al., 1990 ▶) from 3-nitro­indoles, depending on the N-indole protecting group [Pelkey et al., 1996 ▶; Pelkey & Gribble, 1997 ▶, 1999 ▶, 2006 ▶). For recent examples of the Barton–Zard pyrrole synthesis, see: Bobal & Lightner (2001 ▶); Woydziak et al. (2005 ▶); Larionov & deMeijere (2005 ▶); Coffin et al. (2006 ▶); Okujima et al. (2006 ▶); Ono (2008 ▶). For related structures, see: Jackson et al. (1975 ▶); Moody & Ward (1984a ▶,b ▶); Yamane et al. (1986 ▶); Yin et al. (2010 ▶); Tsuji et al. (2002 ▶); Somei et al. (1997 ▶); Kawasaki et al. (2005 ▶); Jasinski et al. (2010 ▶). For MOPAC theoretical calculations, see: Schmidt & Polik (2007 ▶). For standard bond lengths, see: Allen et al. (1987 ▶)

Experimental

Crystal data

C23H18N2O4S2

M = 450.51

Triclinic,

a = 8.1547 (3) Å

b = 11.0471 (5) Å

c = 11.7185 (4) Å

α = 73.834 (4)°

β = 87.131 (3)°

γ = 79.277 (4)°

V = 996.22 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.30 mm−1

T = 123 K

0.41 × 0.36 × 0.29 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Ruby (Gemini) detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.981, T max = 1.000

12580 measured reflections

6592 independent reflections

5331 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.103

S = 1.09

6592 reflections

281 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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 global, I. DOI: 10.1107/S1600536810039425/fl2319sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039425/fl2319Isup2.hkl

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

C23H18N2O4S2	Z = 2
Mr = 450.51	F(000) = 468
Triclinic, P1	Dx = 1.502 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1547 (3) Å	Cell parameters from 7126 reflections
b = 11.0471 (5) Å	θ = 5.0–32.7°
c = 11.7185 (4) Å	µ = 0.30 mm−1
α = 73.834 (4)°	T = 123 K
β = 87.131 (3)°	Prism, colorless
γ = 79.277 (4)°	0.41 × 0.36 × 0.29 mm
V = 996.22 (7) Å3

Oxford Diffraction Xcalibur diffractometer with Ruby (Gemini) detector	6592 independent reflections
Radiation source: Enhance (Cu) X-ray Source	5331 reflections with I > 2σ(I)
graphite	Rint = 0.020
Detector resolution: 10.5081 pixels mm-1	θmax = 32.8°, θmin = 5.1°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −16→16
Tmin = 0.981, Tmax = 1.000	l = −17→13
12580 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0572P)2 + 0.0394P] where P = (Fo2 + 2Fc2)/3
6592 reflections	(Δ/σ)max < 0.001
281 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.33 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
S1	0.24124 (3)	0.40940 (3)	0.21069 (3)	0.01455 (7)
S2	0.53714 (4)	0.07067 (3)	0.67939 (3)	0.01540 (7)
O1	0.28990 (11)	0.27445 (8)	0.22946 (8)	0.01961 (18)
O2	0.10331 (10)	0.48046 (9)	0.13513 (8)	0.01992 (19)
O3	0.61740 (11)	−0.00088 (8)	0.59944 (8)	0.02005 (19)
O4	0.63277 (11)	0.09255 (9)	0.76857 (8)	0.02102 (19)
N1	0.19171 (12)	0.42667 (9)	0.34605 (9)	0.01529 (19)
N2	0.36818 (12)	0.22963 (9)	0.48254 (9)	0.01541 (19)
H2B	0.3722	0.1694	0.4462	0.018*
C1	0.43829 (15)	0.21752 (11)	0.59259 (10)	0.0155 (2)
C2	0.40399 (15)	0.33305 (11)	0.62081 (11)	0.0169 (2)
H2A	0.4367	0.3501	0.6906	0.020*
C3	0.30982 (15)	0.42085 (11)	0.52414 (11)	0.0160 (2)
C4	0.21746 (15)	0.55003 (11)	0.47483 (11)	0.0161 (2)
C5	0.18616 (17)	0.66151 (12)	0.51200 (12)	0.0218 (3)
H5A	0.2306	0.6628	0.5850	0.026*
C6	0.08910 (17)	0.77060 (12)	0.44084 (12)	0.0242 (3)
H6A	0.0680	0.8471	0.4653	0.029*
C7	0.02218 (16)	0.76964 (12)	0.33428 (12)	0.0232 (3)
H7A	−0.0436	0.8457	0.2871	0.028*
C8	0.04966 (15)	0.65990 (12)	0.29554 (12)	0.0200 (2)
H8A	0.0027	0.6588	0.2233	0.024*
C9	0.14851 (14)	0.55177 (11)	0.36653 (11)	0.0159 (2)
C10	0.29295 (14)	0.35350 (11)	0.44405 (10)	0.0146 (2)
C11	0.41636 (14)	0.48258 (11)	0.16669 (10)	0.0142 (2)
C12	0.57366 (15)	0.40983 (12)	0.20143 (11)	0.0186 (2)
H12A	0.5850	0.3233	0.2480	0.022*
C13	0.71326 (15)	0.46588 (13)	0.16684 (12)	0.0214 (3)
H13A	0.8213	0.4177	0.1901	0.026*
C14	0.69552 (16)	0.59186 (13)	0.09850 (11)	0.0210 (3)
H14A	0.7918	0.6295	0.0746	0.025*
C15	0.53830 (17)	0.66374 (13)	0.06448 (12)	0.0214 (3)
H15A	0.5276	0.7502	0.0176	0.026*
C16	0.39661 (15)	0.60964 (12)	0.09882 (11)	0.0184 (2)
H16A	0.2886	0.6584	0.0764	0.022*
C17	0.37346 (15)	−0.00606 (11)	0.75228 (10)	0.0155 (2)
C18	0.34028 (16)	−0.00884 (12)	0.87037 (11)	0.0188 (2)
H18A	0.4056	0.0289	0.9110	0.023*
C19	0.21030 (16)	−0.06741 (12)	0.92891 (11)	0.0197 (2)
H19A	0.1885	−0.0706	1.0100	0.024*
C20	0.11216 (15)	−0.12121 (11)	0.86952 (11)	0.0175 (2)
C21	0.14575 (16)	−0.11501 (12)	0.74970 (11)	0.0188 (2)
H21A	0.0777	−0.1496	0.7080	0.023*
C22	0.27672 (15)	−0.05922 (11)	0.69078 (11)	0.0178 (2)
H22A	0.3001	−0.0573	0.6101	0.021*
C23	−0.02767 (17)	−0.18520 (13)	0.93246 (13)	0.0244 (3)
H23A	−0.0415	−0.1727	1.0122	0.037*
H23B	−0.0010	−0.2771	0.9388	0.037*
H23C	−0.1315	−0.1475	0.8873	0.037*

	U11	U22	U33	U12	U13	U23
S1	0.01309 (13)	0.01663 (14)	0.01399 (14)	−0.00350 (10)	−0.00090 (10)	−0.00358 (10)
S2	0.01639 (14)	0.01312 (13)	0.01499 (14)	−0.00131 (10)	0.00004 (10)	−0.00193 (10)
O1	0.0238 (4)	0.0173 (4)	0.0193 (4)	−0.0061 (3)	−0.0006 (3)	−0.0059 (3)
O2	0.0137 (4)	0.0273 (5)	0.0173 (4)	−0.0036 (3)	−0.0034 (3)	−0.0031 (4)
O3	0.0205 (4)	0.0163 (4)	0.0219 (5)	−0.0005 (3)	0.0043 (3)	−0.0056 (3)
O4	0.0204 (4)	0.0218 (4)	0.0201 (5)	−0.0053 (4)	−0.0037 (3)	−0.0028 (4)
N1	0.0165 (5)	0.0145 (4)	0.0133 (5)	−0.0013 (4)	0.0001 (4)	−0.0022 (4)
N2	0.0189 (5)	0.0120 (4)	0.0147 (5)	−0.0012 (4)	−0.0003 (4)	−0.0036 (4)
C1	0.0183 (5)	0.0139 (5)	0.0127 (5)	−0.0018 (4)	0.0003 (4)	−0.0017 (4)
C2	0.0211 (6)	0.0146 (5)	0.0143 (5)	−0.0028 (4)	0.0004 (4)	−0.0030 (4)
C3	0.0187 (5)	0.0139 (5)	0.0145 (5)	−0.0024 (4)	0.0018 (4)	−0.0033 (4)
C4	0.0167 (5)	0.0141 (5)	0.0156 (5)	−0.0025 (4)	0.0029 (4)	−0.0018 (4)
C5	0.0275 (7)	0.0167 (5)	0.0203 (6)	−0.0016 (5)	0.0019 (5)	−0.0054 (5)
C6	0.0270 (7)	0.0148 (6)	0.0287 (7)	0.0000 (5)	0.0040 (5)	−0.0059 (5)
C7	0.0203 (6)	0.0169 (6)	0.0271 (7)	0.0024 (5)	0.0020 (5)	−0.0014 (5)
C8	0.0175 (6)	0.0186 (6)	0.0201 (6)	0.0007 (5)	−0.0008 (4)	−0.0014 (5)
C9	0.0149 (5)	0.0143 (5)	0.0173 (6)	−0.0019 (4)	0.0040 (4)	−0.0033 (4)
C10	0.0153 (5)	0.0134 (5)	0.0139 (5)	−0.0024 (4)	0.0013 (4)	−0.0020 (4)
C11	0.0120 (5)	0.0178 (5)	0.0134 (5)	−0.0037 (4)	0.0006 (4)	−0.0046 (4)
C12	0.0160 (5)	0.0184 (5)	0.0191 (6)	−0.0007 (4)	−0.0011 (4)	−0.0029 (5)
C13	0.0129 (5)	0.0288 (7)	0.0222 (6)	−0.0022 (5)	−0.0004 (4)	−0.0073 (5)
C14	0.0178 (6)	0.0301 (7)	0.0187 (6)	−0.0112 (5)	0.0043 (4)	−0.0085 (5)
C15	0.0253 (6)	0.0202 (6)	0.0177 (6)	−0.0073 (5)	0.0011 (5)	−0.0019 (5)
C16	0.0177 (5)	0.0188 (5)	0.0165 (6)	−0.0016 (4)	−0.0013 (4)	−0.0019 (4)
C17	0.0171 (5)	0.0114 (5)	0.0153 (5)	−0.0007 (4)	0.0000 (4)	−0.0006 (4)
C18	0.0227 (6)	0.0174 (5)	0.0153 (6)	−0.0035 (5)	−0.0030 (4)	−0.0024 (4)
C19	0.0235 (6)	0.0200 (6)	0.0141 (6)	−0.0035 (5)	0.0010 (4)	−0.0026 (4)
C20	0.0190 (6)	0.0128 (5)	0.0184 (6)	−0.0013 (4)	0.0013 (4)	−0.0018 (4)
C21	0.0226 (6)	0.0151 (5)	0.0197 (6)	−0.0041 (4)	−0.0003 (5)	−0.0057 (4)
C22	0.0224 (6)	0.0148 (5)	0.0153 (6)	−0.0012 (4)	0.0018 (4)	−0.0044 (4)
C23	0.0258 (7)	0.0244 (6)	0.0241 (7)	−0.0098 (5)	0.0058 (5)	−0.0062 (5)

S1—O1	1.4263 (9)	C8—H8A	0.9500
S1—O2	1.4316 (9)	C11—C16	1.3914 (16)
S1—N1	1.6707 (10)	C11—C12	1.3941 (16)
S1—C11	1.7557 (12)	C12—C13	1.3856 (18)
S2—O4	1.4322 (9)	C12—H12A	0.9500
S2—O3	1.4455 (9)	C13—C14	1.3839 (19)
S2—C1	1.7300 (12)	C13—H13A	0.9500
S2—C17	1.7701 (12)	C14—C15	1.3889 (18)
N1—C10	1.4084 (15)	C14—H14A	0.9500
N1—C9	1.4446 (15)	C15—C16	1.3895 (18)
N2—C10	1.3506 (14)	C15—H15A	0.9500
N2—C1	1.3990 (15)	C16—H16A	0.9500
N2—H2B	0.8800	C17—C18	1.3896 (17)
C1—C2	1.3818 (17)	C17—C22	1.3970 (17)
C2—C3	1.4184 (17)	C18—C19	1.3958 (17)
C2—H2A	0.9500	C18—H18A	0.9500
C3—C10	1.3760 (17)	C19—C20	1.3932 (18)
C3—C4	1.4567 (16)	C19—H19A	0.9500
C4—C5	1.3937 (18)	C20—C21	1.4022 (17)
C4—C9	1.4075 (17)	C20—C23	1.5065 (17)
C5—C6	1.3877 (18)	C21—C22	1.3897 (17)
C5—H5A	0.9500	C21—H21A	0.9500
C6—C7	1.391 (2)	C22—H22A	0.9500
C6—H6A	0.9500	C23—H23A	0.9800
C7—C8	1.3861 (19)	C23—H23B	0.9800
C7—H7A	0.9500	C23—H23C	0.9800
C8—C9	1.3871 (16)
O1—S1—O2	121.13 (6)	N2—C10—C3	111.89 (11)
O1—S1—N1	104.32 (5)	N2—C10—N1	134.91 (11)
O2—S1—N1	106.30 (5)	C3—C10—N1	112.99 (10)
O1—S1—C11	109.10 (5)	C16—C11—C12	121.61 (11)
O2—S1—C11	109.09 (5)	C16—C11—S1	120.24 (9)
N1—S1—C11	105.77 (5)	C12—C11—S1	118.15 (9)
O4—S2—O3	120.17 (6)	C13—C12—C11	118.89 (11)
O4—S2—C1	108.32 (6)	C13—C12—H12A	120.6
O3—S2—C1	107.11 (6)	C11—C12—H12A	120.6
O4—S2—C17	107.49 (6)	C14—C13—C12	120.11 (12)
O3—S2—C17	107.91 (6)	C14—C13—H13A	119.9
C1—S2—C17	104.84 (6)	C12—C13—H13A	119.9
C10—N1—C9	103.92 (10)	C13—C14—C15	120.63 (12)
C10—N1—S1	119.83 (8)	C13—C14—H14A	119.7
C9—N1—S1	121.49 (8)	C15—C14—H14A	119.7
C10—N2—C1	105.31 (10)	C14—C15—C16	120.20 (12)
C10—N2—H2B	127.3	C14—C15—H15A	119.9
C1—N2—H2B	127.3	C16—C15—H15A	119.9
C2—C1—N2	110.47 (10)	C15—C16—C11	118.56 (11)
C2—C1—S2	128.02 (10)	C15—C16—H16A	120.7
N2—C1—S2	121.31 (9)	C11—C16—H16A	120.7
C1—C2—C3	105.85 (11)	C18—C17—C22	120.89 (11)
C1—C2—H2A	127.1	C18—C17—S2	118.71 (10)
C3—C2—H2A	127.1	C22—C17—S2	120.37 (9)
C10—C3—C2	106.48 (10)	C17—C18—C19	119.56 (12)
C10—C3—C4	106.28 (10)	C17—C18—H18A	120.2
C2—C3—C4	147.16 (12)	C19—C18—H18A	120.2
C5—C4—C9	118.78 (11)	C20—C19—C18	120.61 (12)
C5—C4—C3	134.52 (12)	C20—C19—H19A	119.7
C9—C4—C3	106.70 (10)	C18—C19—H19A	119.7
C6—C5—C4	119.01 (13)	C19—C20—C21	118.85 (11)
C6—C5—H5A	120.5	C19—C20—C23	120.83 (11)
C4—C5—H5A	120.5	C21—C20—C23	120.31 (12)
C5—C6—C7	121.04 (12)	C22—C21—C20	121.23 (12)
C5—C6—H6A	119.5	C22—C21—H21A	119.4
C7—C6—H6A	119.5	C20—C21—H21A	119.4
C8—C7—C6	121.29 (12)	C21—C22—C17	118.83 (11)
C8—C7—H7A	119.4	C21—C22—H22A	120.6
C6—C7—H7A	119.4	C17—C22—H22A	120.6
C7—C8—C9	117.26 (12)	C20—C23—H23A	109.5
C7—C8—H8A	121.4	C20—C23—H23B	109.5
C9—C8—H8A	121.4	H23A—C23—H23B	109.5
C8—C9—C4	122.62 (11)	C20—C23—H23C	109.5
C8—C9—N1	127.30 (11)	H23A—C23—H23C	109.5
C4—C9—N1	110.05 (10)	H23B—C23—H23C	109.5
O1—S1—N1—C10	42.28 (10)	C2—C3—C10—N2	0.36 (14)
O2—S1—N1—C10	171.37 (9)	C4—C3—C10—N2	−177.43 (10)
C11—S1—N1—C10	−72.74 (10)	C2—C3—C10—N1	175.95 (10)
O1—S1—N1—C9	174.84 (9)	C4—C3—C10—N1	−1.84 (13)
O2—S1—N1—C9	−56.07 (10)	C9—N1—C10—N2	176.61 (13)
C11—S1—N1—C9	59.82 (10)	S1—N1—C10—N2	−43.72 (18)
C10—N2—C1—C2	0.64 (13)	C9—N1—C10—C3	2.39 (13)
C10—N2—C1—S2	175.91 (9)	S1—N1—C10—C3	142.06 (9)
O4—S2—C1—C2	−20.80 (13)	O1—S1—C11—C16	154.12 (10)
O3—S2—C1—C2	−151.78 (11)	O2—S1—C11—C16	19.79 (12)
C17—S2—C1—C2	93.73 (12)	N1—S1—C11—C16	−94.18 (11)
O4—S2—C1—N2	164.83 (9)	O1—S1—C11—C12	−25.73 (11)
O3—S2—C1—N2	33.85 (11)	O2—S1—C11—C12	−160.07 (10)
C17—S2—C1—N2	−80.63 (10)	N1—S1—C11—C12	85.96 (11)
N2—C1—C2—C3	−0.43 (14)	C16—C11—C12—C13	−0.25 (19)
S2—C1—C2—C3	−175.30 (9)	S1—C11—C12—C13	179.61 (10)
C1—C2—C3—C10	0.05 (13)	C11—C12—C13—C14	−0.3 (2)
C1—C2—C3—C4	176.14 (18)	C12—C13—C14—C15	0.4 (2)
C10—C3—C4—C5	179.76 (14)	C13—C14—C15—C16	0.0 (2)
C2—C3—C4—C5	3.7 (3)	C14—C15—C16—C11	−0.49 (19)
C10—C3—C4—C9	0.47 (13)	C12—C11—C16—C15	0.64 (19)
C2—C3—C4—C9	−175.62 (18)	S1—C11—C16—C15	−179.22 (10)
C9—C4—C5—C6	−0.39 (18)	O4—S2—C17—C18	12.96 (11)
C3—C4—C5—C6	−179.62 (13)	O3—S2—C17—C18	143.93 (9)
C4—C5—C6—C7	0.5 (2)	C1—S2—C17—C18	−102.15 (10)
C5—C6—C7—C8	0.1 (2)	O4—S2—C17—C22	−168.94 (9)
C6—C7—C8—C9	−0.90 (19)	O3—S2—C17—C22	−37.97 (11)
C7—C8—C9—C4	1.05 (18)	C1—S2—C17—C22	75.95 (11)
C7—C8—C9—N1	178.71 (12)	C22—C17—C18—C19	1.07 (17)
C5—C4—C9—C8	−0.41 (18)	S2—C17—C18—C19	179.16 (9)
C3—C4—C9—C8	179.01 (11)	C17—C18—C19—C20	−1.00 (18)
C5—C4—C9—N1	−178.44 (11)	C18—C19—C20—C21	−0.28 (18)
C3—C4—C9—N1	0.99 (13)	C18—C19—C20—C23	179.65 (11)
C10—N1—C9—C8	−179.91 (11)	C19—C20—C21—C22	1.53 (18)
S1—N1—C9—C8	41.26 (16)	C23—C20—C21—C22	−178.40 (11)
C10—N1—C9—C4	−2.01 (12)	C20—C21—C22—C17	−1.47 (18)
S1—N1—C9—C4	−140.84 (9)	C18—C17—C22—C21	0.15 (17)
C1—N2—C10—C3	−0.61 (13)	S2—C17—C22—C21	−177.91 (9)
C1—N2—C10—N1	−174.88 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O3i	0.88	2.06	2.9244 (14)	167
C13—H13A···O2ii	0.95	2.53	3.2125 (15)	129
C22—H22A···O3i	0.95	2.45	3.3786 (15)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O3i	0.88	2.06	2.9244 (14)	167
C13—H13A⋯O2ii	0.95	2.53	3.2125 (15)	129
C22—H22A⋯O3i	0.95	2.45	3.3786 (15)	165

Symmetry codes: (i) ; (ii) .