7-Bromo-3-ethyl-9-phenyl-2-tosyl-pyrrolo[3,4-b]quinoline.

In the title compound, C(26)H(27)BrN(2)O(2)S, the pyrrolidine ring adopts a twist conformation, while the tetra-hydro-pyridine ring is in a half-chair conformation. The two rings are trans-fused. The dihedral angle between the phenyl ring and the sulfonyl-bound benzene ring is 22.83 (7)°. N-H⋯O hydrogen bonds link the mol-ecules into a chain along the b axis, and the chains are cross-linked into a three-dimensional network by a C-H⋯π inter-action and a weak π-π inter-action between the sulfonyl-bound benzene rings; the centroid-centroid distance is 3.6957 (8) Å.

Related literature

The crystal structure of the title compound is similar to that of its chloro analogue (Sudha et al., 2007 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Duax et al. (1976 ▶).

Experimental

Crystal data

C26H27BrN2O2S

M = 511.47

Monoclinic,

a = 9.6293 (2) Å

b = 13.4574 (3) Å

c = 20.2179 (4) Å

β = 116.930 (1)°

V = 2335.84 (9) Å3

Z = 4

Mo Kα radiation

μ = 1.88 mm−1

T = 100.0 (1) K

0.58 × 0.52 × 0.34 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.323, T max = 0.529

58171 measured reflections

14302 independent reflections

9599 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.094

S = 1.01

14302 reflections

294 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.13 e Å−3

Δρmin = −0.63 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 1998 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063222/is2257sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063222/is2257Isup2.hkl

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

C26H27BrN2O2S	F000 = 1056
Mr = 511.47	Dx = 1.454 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5745 reflections
a = 9.6293 (2) Å	θ = 2.4–38.4º
b = 13.4574 (3) Å	µ = 1.88 mm−1
c = 20.2179 (4) Å	T = 100.0 (1) K
β = 116.930 (1)º	Block, colourless
V = 2335.84 (9) Å3	0.58 × 0.52 × 0.34 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	14302 independent reflections
Radiation source: fine-focus sealed tube	9599 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.055
Detector resolution: 8.33 pixels mm-1	θmax = 40.0º
T = 100.0(1) K	θmin = 2.3º
ω scans	h = −16→17
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −24→23
Tmin = 0.323, Tmax = 0.529	l = −36→36
58171 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0418P)2 + 0.5198P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
14302 reflections	Δρmax = 1.13 e Å−3
294 parameters	Δρmin = −0.63 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Br1	0.009166 (12)	0.383484 (9)	−0.061858 (7)	0.01903 (3)
S1	1.10805 (3)	0.50065 (2)	0.342333 (16)	0.01644 (5)
O1	1.16380 (10)	0.60150 (7)	0.35422 (6)	0.02221 (18)
O2	1.21739 (10)	0.42008 (7)	0.36992 (5)	0.02180 (17)
N1	1.00957 (10)	0.48551 (7)	0.25246 (6)	0.01539 (16)
N2	0.70188 (11)	0.31729 (7)	0.13123 (6)	0.01682 (17)
H1N2	0.738 (2)	0.2632 (16)	0.1260 (10)	0.024 (4)*
C1	0.87389 (12)	0.55496 (8)	0.21501 (6)	0.01499 (18)
H1A	0.8835	0.5940	0.1770	0.018*
H1B	0.8642	0.5993	0.2505	0.018*
C2	0.73638 (11)	0.48360 (8)	0.18133 (6)	0.01310 (16)
H2	0.7174	0.4574	0.2217	0.016*
C3	0.58180 (11)	0.52210 (8)	0.12093 (6)	0.01333 (16)
H3	0.6032	0.5603	0.0853	0.016*
C4	0.48065 (12)	0.43277 (8)	0.08039 (6)	0.01331 (16)
C5	0.32017 (12)	0.44516 (8)	0.03642 (6)	0.01504 (17)
H5	0.2750	0.5070	0.0341	0.018*
C6	0.22782 (12)	0.36598 (8)	−0.00374 (6)	0.01598 (18)
C7	0.29217 (13)	0.27321 (9)	−0.00227 (7)	0.01821 (19)
H7	0.2302	0.2211	−0.0305	0.022*
C8	0.45046 (13)	0.25954 (9)	0.04208 (7)	0.01821 (19)
H8	0.4942	0.1974	0.0438	0.022*
C9	0.54584 (12)	0.33745 (8)	0.08428 (6)	0.01469 (17)
C10	0.80650 (12)	0.40097 (8)	0.15527 (6)	0.01407 (17)
H10	0.8271	0.4245	0.1147	0.017*
C11	0.95981 (12)	0.38117 (8)	0.22454 (6)	0.01524 (17)
H11	0.9365	0.3457	0.2607	0.018*
C12	0.97389 (13)	0.48916 (9)	0.37889 (7)	0.01797 (19)
C13	0.93661 (13)	0.39511 (9)	0.39459 (7)	0.0197 (2)
H13	0.9872	0.3392	0.3891	0.024*
C14	0.82254 (14)	0.38560 (11)	0.41864 (7)	0.0231 (2)
H14	0.7998	0.3231	0.4308	0.028*
C15	0.74214 (15)	0.46833 (12)	0.42474 (7)	0.0246 (2)
C16	0.78110 (17)	0.56192 (12)	0.40851 (8)	0.0274 (3)
H16	0.7283	0.6177	0.4125	0.033*
C17	0.89758 (16)	0.57311 (10)	0.38651 (8)	0.0233 (2)
H17	0.9244	0.6360	0.3770	0.028*
C18	0.61530 (19)	0.45797 (15)	0.44829 (10)	0.0352 (3)
H18A	0.6093	0.3901	0.4613	0.053*
H18B	0.5175	0.4774	0.4081	0.053*
H18C	0.6382	0.4998	0.4904	0.053*
C19	0.51164 (12)	0.59192 (8)	0.15662 (6)	0.01492 (18)
C20	0.53584 (13)	0.69413 (9)	0.15655 (7)	0.0195 (2)
H20	0.5836	0.7198	0.1293	0.023*
C21	0.48931 (15)	0.75812 (10)	0.19693 (8)	0.0268 (3)
H21	0.5076	0.8260	0.1971	0.032*
C22	0.41570 (16)	0.72071 (12)	0.23691 (8)	0.0295 (3)
H22	0.3846	0.7634	0.2639	0.035*
C23	0.38881 (16)	0.61938 (12)	0.23646 (8)	0.0281 (3)
H23	0.3378	0.5943	0.2624	0.034*
C24	0.43787 (14)	0.55503 (10)	0.19723 (7)	0.0213 (2)
H24	0.4214	0.4870	0.1981	0.026*
C25	1.08137 (13)	0.32202 (9)	0.21256 (7)	0.0192 (2)
H25A	1.1749	0.3178	0.2595	0.023*
H25B	1.0426	0.2549	0.1982	0.023*
C26	1.12569 (16)	0.36324 (11)	0.15477 (9)	0.0265 (3)
H26A	1.2025	0.3210	0.1513	0.040*
H26B	1.1676	0.4289	0.1689	0.040*
H26C	1.0350	0.3659	0.1075	0.040*

	U11	U22	U33	U12	U13	U23
Br1	0.01395 (4)	0.02093 (5)	0.01897 (6)	−0.00094 (4)	0.00462 (4)	−0.00109 (4)
S1	0.01233 (9)	0.01608 (11)	0.01730 (12)	−0.00234 (8)	0.00355 (8)	0.00071 (9)
O1	0.0193 (4)	0.0188 (4)	0.0239 (5)	−0.0068 (3)	0.0058 (3)	−0.0019 (3)
O2	0.0137 (3)	0.0224 (4)	0.0233 (4)	0.0014 (3)	0.0031 (3)	0.0035 (3)
N1	0.0130 (3)	0.0142 (4)	0.0165 (4)	0.0004 (3)	0.0046 (3)	0.0013 (3)
N2	0.0143 (3)	0.0113 (4)	0.0230 (5)	0.0005 (3)	0.0068 (3)	−0.0021 (3)
C1	0.0139 (4)	0.0123 (4)	0.0172 (5)	−0.0001 (3)	0.0057 (3)	0.0005 (3)
C2	0.0128 (3)	0.0117 (4)	0.0150 (4)	0.0002 (3)	0.0064 (3)	−0.0001 (3)
C3	0.0136 (4)	0.0126 (4)	0.0143 (4)	0.0000 (3)	0.0067 (3)	−0.0001 (3)
C4	0.0140 (4)	0.0128 (4)	0.0137 (4)	−0.0004 (3)	0.0068 (3)	−0.0002 (3)
C5	0.0151 (4)	0.0150 (4)	0.0150 (5)	0.0005 (3)	0.0067 (3)	0.0001 (3)
C6	0.0140 (4)	0.0170 (5)	0.0155 (5)	−0.0018 (3)	0.0054 (3)	−0.0011 (4)
C7	0.0172 (4)	0.0156 (4)	0.0199 (5)	−0.0028 (3)	0.0067 (4)	−0.0028 (4)
C8	0.0176 (4)	0.0133 (4)	0.0218 (5)	−0.0011 (3)	0.0072 (4)	−0.0024 (4)
C9	0.0147 (4)	0.0131 (4)	0.0163 (5)	0.0001 (3)	0.0070 (3)	0.0000 (3)
C10	0.0128 (4)	0.0126 (4)	0.0166 (5)	0.0002 (3)	0.0064 (3)	−0.0001 (3)
C11	0.0141 (4)	0.0133 (4)	0.0172 (5)	0.0001 (3)	0.0061 (3)	0.0009 (4)
C12	0.0157 (4)	0.0206 (5)	0.0148 (5)	−0.0023 (3)	0.0045 (4)	0.0004 (4)
C13	0.0157 (4)	0.0215 (5)	0.0183 (5)	−0.0002 (3)	0.0045 (4)	0.0045 (4)
C14	0.0195 (5)	0.0283 (6)	0.0191 (5)	−0.0039 (4)	0.0068 (4)	0.0039 (5)
C15	0.0231 (5)	0.0342 (7)	0.0169 (5)	−0.0046 (5)	0.0094 (4)	−0.0031 (5)
C16	0.0328 (6)	0.0282 (7)	0.0260 (7)	−0.0002 (5)	0.0176 (5)	−0.0061 (5)
C17	0.0300 (6)	0.0197 (5)	0.0228 (6)	−0.0022 (4)	0.0141 (5)	−0.0038 (4)
C18	0.0327 (7)	0.0498 (10)	0.0309 (8)	−0.0065 (6)	0.0212 (6)	−0.0053 (7)
C19	0.0133 (4)	0.0147 (4)	0.0157 (5)	0.0018 (3)	0.0056 (3)	−0.0021 (3)
C20	0.0185 (4)	0.0152 (5)	0.0220 (6)	0.0024 (3)	0.0067 (4)	−0.0019 (4)
C21	0.0241 (5)	0.0196 (5)	0.0304 (7)	0.0064 (4)	0.0067 (5)	−0.0080 (5)
C22	0.0244 (5)	0.0361 (7)	0.0248 (6)	0.0097 (5)	0.0084 (5)	−0.0108 (5)
C23	0.0251 (5)	0.0393 (8)	0.0240 (6)	0.0039 (5)	0.0146 (5)	−0.0052 (6)
C24	0.0210 (5)	0.0242 (6)	0.0216 (6)	0.0001 (4)	0.0123 (4)	−0.0023 (4)
C25	0.0162 (4)	0.0161 (5)	0.0244 (6)	0.0032 (3)	0.0083 (4)	0.0012 (4)
C26	0.0230 (5)	0.0265 (6)	0.0361 (8)	0.0056 (4)	0.0188 (5)	0.0046 (5)

Br1—C6	1.9048 (11)	C12—C13	1.3909 (17)
S1—O2	1.4363 (10)	C12—C17	1.3937 (19)
S1—O1	1.4392 (9)	C13—C14	1.3940 (18)
S1—N1	1.6375 (10)	C13—H13	0.93
S1—C12	1.7619 (12)	C14—C15	1.393 (2)
N1—C1	1.5025 (14)	C14—H14	0.93
N1—C11	1.5083 (15)	C15—C16	1.395 (2)
N2—C9	1.3930 (14)	C15—C18	1.505 (2)
N2—C10	1.4408 (14)	C16—C17	1.389 (2)
N2—H1N2	0.83 (2)	C16—H16	0.93
C1—C2	1.5239 (14)	C17—H17	0.93
C1—H1A	0.97	C18—H18A	0.96
C1—H1B	0.97	C18—H18B	0.96
C2—C10	1.5140 (15)	C18—H18C	0.96
C2—C3	1.5260 (14)	C19—C20	1.3952 (16)
C2—H2	0.98	C19—C24	1.3976 (17)
C3—C19	1.5171 (15)	C20—C21	1.3929 (18)
C3—C4	1.5306 (15)	C20—H20	0.93
C3—H3	0.98	C21—C22	1.389 (2)
C4—C5	1.4006 (14)	C21—H21	0.93
C4—C9	1.4145 (15)	C22—C23	1.387 (2)
C5—C6	1.3898 (15)	C22—H22	0.93
C5—H5	0.93	C23—C24	1.3933 (19)
C6—C7	1.3881 (17)	C23—H23	0.93
C7—C8	1.3867 (16)	C24—H24	0.93
C7—H7	0.93	C25—C26	1.5188 (19)
C8—C9	1.4003 (16)	C25—H25A	0.97
C8—H8	0.93	C25—H25B	0.97
C10—C11	1.5294 (15)	C26—H26A	0.96
C10—H10	0.98	C26—H26B	0.96
C11—C25	1.5230 (16)	C26—H26C	0.96
C11—H11	0.98
O2—S1—O1	119.64 (6)	N1—C11—H11	108.4
O2—S1—N1	106.93 (6)	C25—C11—H11	108.4
O1—S1—N1	106.70 (6)	C10—C11—H11	108.4
O2—S1—C12	108.58 (6)	C13—C12—C17	120.60 (12)
O1—S1—C12	107.56 (6)	C13—C12—S1	119.32 (10)
N1—S1—C12	106.77 (5)	C17—C12—S1	119.91 (10)
C1—N1—C11	109.52 (8)	C12—C13—C14	119.25 (12)
C1—N1—S1	114.59 (8)	C12—C13—H13	120.4
C11—N1—S1	117.20 (8)	C14—C13—H13	120.4
C9—N2—C10	116.82 (9)	C15—C14—C13	120.98 (12)
C9—N2—H1N2	117.8 (13)	C15—C14—H14	119.5
C10—N2—H1N2	117.2 (13)	C13—C14—H14	119.5
N1—C1—C2	102.39 (8)	C14—C15—C16	118.77 (12)
N1—C1—H1A	111.3	C14—C15—C18	121.14 (14)
C2—C1—H1A	111.3	C16—C15—C18	120.09 (14)
N1—C1—H1B	111.3	C17—C16—C15	121.01 (13)
C2—C1—H1B	111.3	C17—C16—H16	119.5
H1A—C1—H1B	109.2	C15—C16—H16	119.5
C10—C2—C1	100.61 (8)	C16—C17—C12	119.34 (13)
C10—C2—C3	113.45 (9)	C16—C17—H17	120.3
C1—C2—C3	118.62 (9)	C12—C17—H17	120.3
C10—C2—H2	107.9	C15—C18—H18A	109.5
C1—C2—H2	107.9	C15—C18—H18B	109.5
C3—C2—H2	107.9	H18A—C18—H18B	109.5
C19—C3—C2	108.23 (9)	C15—C18—H18C	109.5
C19—C3—C4	115.39 (9)	H18A—C18—H18C	109.5
C2—C3—C4	108.39 (9)	H18B—C18—H18C	109.5
C19—C3—H3	108.2	C20—C19—C24	118.71 (11)
C2—C3—H3	108.2	C20—C19—C3	119.97 (10)
C4—C3—H3	108.2	C24—C19—C3	120.91 (10)
C5—C4—C9	118.53 (10)	C21—C20—C19	120.71 (13)
C5—C4—C3	119.87 (9)	C21—C20—H20	119.6
C9—C4—C3	121.58 (9)	C19—C20—H20	119.6
C6—C5—C4	120.63 (10)	C22—C21—C20	120.10 (13)
C6—C5—H5	119.7	C22—C21—H21	120.0
C4—C5—H5	119.7	C20—C21—H21	120.0
C7—C6—C5	121.05 (10)	C23—C22—C21	119.70 (12)
C7—C6—Br1	118.84 (8)	C23—C22—H22	120.1
C5—C6—Br1	120.10 (8)	C21—C22—H22	120.1
C8—C7—C6	118.84 (10)	C22—C23—C24	120.29 (14)
C8—C7—H7	120.6	C22—C23—H23	119.9
C6—C7—H7	120.6	C24—C23—H23	119.9
C7—C8—C9	121.34 (11)	C23—C24—C19	120.47 (13)
C7—C8—H8	119.3	C23—C24—H24	119.8
C9—C8—H8	119.3	C19—C24—H24	119.8
N2—C9—C8	118.47 (10)	C26—C25—C11	115.82 (10)
N2—C9—C4	121.95 (10)	C26—C25—H25A	108.3
C8—C9—C4	119.54 (10)	C11—C25—H25A	108.3
N2—C10—C2	109.73 (9)	C26—C25—H25B	108.3
N2—C10—C11	114.21 (9)	C11—C25—H25B	108.3
C2—C10—C11	101.94 (9)	H25A—C25—H25B	107.4
N2—C10—H10	110.2	C25—C26—H26A	109.5
C2—C10—H10	110.2	C25—C26—H26B	109.5
C11—C10—H10	110.2	H26A—C26—H26B	109.5
N1—C11—C25	114.16 (9)	C25—C26—H26C	109.5
N1—C11—C10	101.06 (8)	H26A—C26—H26C	109.5
C25—C11—C10	115.98 (10)	H26B—C26—H26C	109.5
O2—S1—N1—C1	171.86 (8)	C1—N1—C11—C25	140.52 (10)
O1—S1—N1—C1	−59.00 (9)	S1—N1—C11—C25	−86.74 (11)
C12—S1—N1—C1	55.78 (9)	C1—N1—C11—C10	15.29 (11)
O2—S1—N1—C11	41.45 (9)	S1—N1—C11—C10	148.03 (8)
O1—S1—N1—C11	170.58 (8)	N2—C10—C11—N1	−158.08 (9)
C12—S1—N1—C11	−74.64 (9)	C2—C10—C11—N1	−39.82 (10)
C11—N1—C1—C2	14.81 (12)	N2—C10—C11—C25	77.92 (13)
S1—N1—C1—C2	−119.27 (8)	C2—C10—C11—C25	−163.81 (9)
N1—C1—C2—C10	−39.19 (10)	O2—S1—C12—C13	−30.53 (11)
N1—C1—C2—C3	−163.49 (9)	O1—S1—C12—C13	−161.35 (9)
C10—C2—C3—C19	171.06 (9)	N1—S1—C12—C13	84.45 (10)
C1—C2—C3—C19	−71.20 (12)	O2—S1—C12—C17	154.32 (10)
C10—C2—C3—C4	45.25 (12)	O1—S1—C12—C17	23.50 (12)
C1—C2—C3—C4	162.98 (9)	N1—S1—C12—C17	−90.71 (11)
C19—C3—C4—C5	41.53 (14)	C17—C12—C13—C14	−0.47 (18)
C2—C3—C4—C5	163.04 (10)	S1—C12—C13—C14	−175.59 (9)
C19—C3—C4—C9	−140.35 (11)	C12—C13—C14—C15	2.16 (19)
C2—C3—C4—C9	−18.85 (14)	C13—C14—C15—C16	−2.0 (2)
C9—C4—C5—C6	−1.42 (17)	C13—C14—C15—C18	177.98 (13)
C3—C4—C5—C6	176.75 (10)	C14—C15—C16—C17	0.1 (2)
C4—C5—C6—C7	−0.96 (18)	C18—C15—C16—C17	−179.85 (14)
C4—C5—C6—Br1	178.88 (9)	C15—C16—C17—C12	1.5 (2)
C5—C6—C7—C8	2.08 (19)	C13—C12—C17—C16	−1.4 (2)
Br1—C6—C7—C8	−177.76 (10)	S1—C12—C17—C16	173.74 (11)
C6—C7—C8—C9	−0.81 (19)	C2—C3—C19—C20	95.33 (12)
C10—N2—C9—C8	160.86 (11)	C4—C3—C19—C20	−143.08 (11)
C10—N2—C9—C4	−21.63 (16)	C2—C3—C19—C24	−77.22 (12)
C7—C8—C9—N2	176.02 (11)	C4—C3—C19—C24	44.37 (14)
C7—C8—C9—C4	−1.56 (18)	C24—C19—C20—C21	0.84 (17)
C5—C4—C9—N2	−174.85 (11)	C3—C19—C20—C21	−171.88 (11)
C3—C4—C9—N2	7.01 (17)	C19—C20—C21—C22	−1.04 (19)
C5—C4—C9—C8	2.64 (17)	C20—C21—C22—C23	0.0 (2)
C3—C4—C9—C8	−175.50 (11)	C21—C22—C23—C24	1.2 (2)
C9—N2—C10—C2	47.11 (14)	C22—C23—C24—C19	−1.4 (2)
C9—N2—C10—C11	160.83 (10)	C20—C19—C24—C23	0.37 (18)
C1—C2—C10—N2	171.23 (9)	C3—C19—C24—C23	173.02 (11)
C3—C2—C10—N2	−61.01 (12)	N1—C11—C25—C26	−62.22 (14)
C1—C2—C10—C11	49.81 (10)	C10—C11—C25—C26	54.68 (14)
C3—C2—C10—C11	177.58 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1i	0.83 (2)	2.33 (2)	3.1381 (14)	162 (2)
C25—H25A···O2	0.97	2.49	3.1312 (15)	123
C3—H3···Cg1ii	0.98	2.83	3.7921 (12)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1i	0.83 (2)	2.33 (2)	3.1381 (14)	162 (2)
C25—H25A⋯O2	0.97	2.49	3.1312 (15)	123
C3—H3⋯Cg1ii	0.98	2.83	3.7921 (12)	168

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C4–C9 benzene ring.