4-[(1,3-Dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-2-yl)meth-yl]-N'-[(E)-4-nitro-benzyl-idene]benzene-sulfono-hydrazide dimethyl sulfoxide monosolvate.

The mol-ecular structure of the title compound, C(26)H(18)N(4)O(6)S·C(2)H(6)OS, shows an E conformation of the hydrazone double bond. The presence of a methyl-ene group between the benzo[de]isoquinoline and benzene-sulfonyl moieties allows the 4-nitro-phenyl ring and the benzo[de]isoquinoline system to be parallel with respect to each other, so that the mol-ecule adopts a U-shaped spatial conformation. The dihedral angle between mean planes of these aromatic groups is 4.4 (1)°. This special arrangement enables neighboring mol-ecules to be inter-calated, forming slipped π-π inter-actions [centroid-centroid distance = 3.535 (2) Å] between the 4-nitro-phenyl and benzo[de]isoquinoline groups and point-to-face C-H⋯π inter-actions between the benzo[de]isoquinoline and benzene-sulfonyl aromatic systems. In addition, the crystal packing also features an inter-molecular N-H⋯O inter-action involving the amine group and the dimethyl sulfoxide solvent mol-ecule.

Related literature

For the therapeutic properties of sulfonyl­hydrazones, see: Rollas et al. (2002 ▶); Frlan et al. (2008 ▶); Lima et al. (1999 ▶); Sondhi et al. (2006 ▶) and for their biological activity, see: Kendall et al. (2007 ▶); Sadek et al. (2008 ▶). For the anti­cancer activity of naphthalimides, see: Braña & Ramos (2001 ▶); Braña et al. (2001 ▶); Suárez & Sánchez (1992 ▶); Ingrassia et al. (2009 ▶); Wu et al. (2009 ▶); Norton et al. (2008 ▶). For the therapeutic properties of cyclic imides, see: Cechinel Filho et al. (2003 ▶); Walter et al. (2002 ▶). For background to this study, see: Silva et al. (2006 ▶); Oliveira & Nunes (2006 ▶).

Experimental

Crystal data

C26H18N4O6S·C2H6OS

M = 592.63

Triclinic,

a = 9.152 (1) Å

b = 11.971 (1) Å

c = 13.910 (1) Å

α = 107.268 (7)°

β = 101.789 (7)°

γ = 96.319 (8)°

V = 1400.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 293 K

0.50 × 0.16 × 0.13 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

5055 measured reflections

4737 independent reflections

3075 reflections with I > 2σ(I)

R int = 0.017

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.163

S = 1.04

4737 reflections

371 parameters

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.43 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: HELENA (Spek, 1996 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811004697/ff2001sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004697/ff2001Isup2.hkl

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

C26H18N4O6S·C2H6OS	Z = 2
Mr = 592.63	F(000) = 616
Triclinic, P1	Dx = 1.405 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.152 (1) Å	Cell parameters from 25 reflections
b = 11.971 (1) Å	θ = 8.5–13.4°
c = 13.910 (1) Å	µ = 0.24 mm−1
α = 107.268 (7)°	T = 293 K
β = 101.789 (7)°	Prismatic, colourless
γ = 96.319 (8)°	0.50 × 0.16 × 0.13 mm
V = 1400.6 (2) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.017
Radiation source: fine-focus sealed tube	θmax = 25.1°, θmin = 2.3°
graphite	h = 0→10
ω–2θ scans	k = −14→14
5055 measured reflections	l = −16→16
4737 independent reflections	3 standard reflections every 200 reflections
3075 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0792P)2 + 0.613P] where P = (Fo2 + 2Fc2)/3
4737 reflections	(Δ/σ)max < 0.001
371 parameters	Δρmax = 0.73 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.34031 (11)	0.73620 (8)	0.53120 (6)	0.0597 (3)
N1	0.8354 (3)	1.1992 (2)	0.8805 (2)	0.0571 (7)
N2	0.4477 (3)	0.6426 (2)	0.55446 (19)	0.0540 (7)
H2N	0.5170	0.6398	0.5273	0.058 (12)*
N3	0.4776 (3)	0.6399 (2)	0.65605 (19)	0.0501 (6)
O1	0.6771 (4)	1.2526 (3)	0.9840 (2)	0.1026 (11)
O2	0.9903 (3)	1.1379 (3)	0.7756 (2)	0.0987 (10)
O3	0.3260 (3)	0.7192 (2)	0.42331 (18)	0.0797 (8)
O4	0.2088 (3)	0.7188 (2)	0.5685 (2)	0.0766 (8)
C2	0.7994 (4)	1.2237 (3)	0.9760 (3)	0.0626 (9)
C3	0.9105 (4)	1.2127 (3)	1.0630 (2)	0.0547 (8)
C4	0.8859 (5)	1.2441 (4)	1.1612 (3)	0.0767 (11)
H4	0.7994	1.2747	1.1724	0.092*
C5	0.9881 (6)	1.2309 (4)	1.2432 (3)	0.0864 (13)
H5	0.9706	1.2547	1.3092	0.104*
C6	1.1117 (6)	1.1846 (4)	1.2296 (3)	0.0803 (13)
H6	1.1779	1.1753	1.2858	0.096*
C7	1.1429 (4)	1.1495 (3)	1.1304 (3)	0.0645 (10)
C8	1.2697 (5)	1.1010 (4)	1.1103 (5)	0.0918 (15)
H8	1.3383	1.0895	1.1643	0.110*
C9	1.2953 (5)	1.0705 (4)	1.0149 (6)	0.1053 (19)
H9	1.3799	1.0370	1.0038	0.126*
C10	1.1970 (5)	1.0884 (4)	0.9325 (4)	0.0845 (13)
H10	1.2170	1.0683	0.8672	0.101*
C11	1.0701 (4)	1.1359 (3)	0.9479 (3)	0.0547 (8)
C12	1.0410 (4)	1.1663 (3)	1.0464 (3)	0.0492 (8)
C13	0.9662 (4)	1.1572 (3)	0.8612 (3)	0.0636 (10)
C14	0.7269 (5)	1.2149 (3)	0.7930 (3)	0.0737 (11)
H14A	0.7827	1.2462	0.7515	0.088*
H14B	0.6660	1.2723	0.8202	0.088*
C15	0.6233 (4)	1.0984 (3)	0.7248 (3)	0.0602 (9)
C16	0.6623 (5)	1.0275 (3)	0.6388 (3)	0.0680 (10)
H16	0.7496	1.0539	0.6214	0.082*
C17	0.5738 (4)	0.9184 (3)	0.5784 (3)	0.0636 (9)
H17	0.6009	0.8715	0.5208	0.076*
C18	0.4443 (4)	0.8797 (3)	0.6049 (2)	0.0535 (8)
C19	0.4011 (4)	0.9501 (4)	0.6880 (3)	0.0714 (10)
H19	0.3127	0.9246	0.7045	0.086*
C20	0.4909 (5)	1.0596 (4)	0.7469 (3)	0.0765 (11)
H20	0.4611	1.1079	0.8027	0.092*
C21	0.5844 (4)	0.5873 (3)	0.6806 (2)	0.0500 (8)
H21	0.6372	0.5541	0.6320	0.060*
C22	0.6255 (4)	0.5781 (3)	0.7849 (2)	0.0475 (7)
C23	0.7517 (4)	0.5304 (3)	0.8140 (3)	0.0580 (9)
H23	0.8057	0.4994	0.7655	0.070*
C24	0.7984 (4)	0.5285 (3)	0.9143 (3)	0.0613 (9)
H24	0.8839	0.4973	0.9341	0.074*
C25	0.7162 (4)	0.5734 (3)	0.9838 (2)	0.0550 (8)
C26	0.5894 (4)	0.6196 (3)	0.9578 (3)	0.0638 (9)
H26	0.5356	0.6495	1.0067	0.077*
C27	0.5431 (4)	0.6209 (3)	0.8576 (3)	0.0615 (9)
H27	0.4561	0.6507	0.8382	0.074*
N4	0.7691 (4)	0.5767 (3)	1.0923 (3)	0.0733 (9)
O5	0.6974 (4)	0.6209 (4)	1.1535 (2)	0.1111 (12)
O6	0.8819 (4)	0.5387 (4)	1.1166 (2)	0.1188 (13)
S2	0.74498 (12)	0.64956 (10)	0.39415 (8)	0.0747 (3)
O1S	0.7208 (3)	0.6673 (3)	0.5003 (2)	0.0830 (8)
C1S	0.8748 (5)	0.5522 (4)	0.3777 (3)	0.0833 (12)
H1S1	0.8257	0.4734	0.3689	0.125*
H1S2	0.9591	0.5784	0.4379	0.125*
H1S3	0.9105	0.5515	0.3173	0.125*
C2S	0.8693 (6)	0.7814 (4)	0.4070 (4)	0.1081 (17)
H2S1	0.8157	0.8468	0.4170	0.162*
H2S2	0.9049	0.7705	0.3451	0.162*
H2S3	0.9542	0.7979	0.4657	0.162*

	U11	U22	U33	U12	U13	U23
S1	0.0667 (6)	0.0595 (5)	0.0449 (5)	−0.0013 (4)	−0.0036 (4)	0.0219 (4)
N1	0.0665 (19)	0.0523 (16)	0.0478 (16)	0.0087 (14)	0.0064 (14)	0.0155 (13)
N2	0.0696 (19)	0.0552 (16)	0.0371 (14)	0.0016 (14)	0.0122 (14)	0.0193 (12)
N3	0.0566 (16)	0.0536 (15)	0.0412 (14)	0.0033 (13)	0.0094 (12)	0.0217 (12)
O1	0.084 (2)	0.137 (3)	0.079 (2)	0.060 (2)	0.0151 (16)	0.0140 (19)
O2	0.103 (2)	0.127 (3)	0.0623 (18)	−0.0099 (19)	0.0389 (17)	0.0240 (17)
O3	0.113 (2)	0.0723 (17)	0.0391 (13)	−0.0025 (15)	−0.0086 (13)	0.0230 (12)
O4	0.0539 (15)	0.0878 (19)	0.0830 (19)	0.0021 (13)	0.0062 (13)	0.0319 (15)
C2	0.064 (2)	0.062 (2)	0.055 (2)	0.0181 (18)	0.0125 (18)	0.0088 (17)
C3	0.059 (2)	0.055 (2)	0.0449 (19)	0.0089 (16)	0.0094 (16)	0.0111 (15)
C4	0.077 (3)	0.085 (3)	0.059 (2)	0.014 (2)	0.019 (2)	0.010 (2)
C5	0.103 (4)	0.097 (3)	0.046 (2)	−0.003 (3)	0.011 (2)	0.019 (2)
C6	0.094 (3)	0.068 (3)	0.062 (3)	−0.011 (2)	−0.012 (2)	0.028 (2)
C7	0.058 (2)	0.0424 (18)	0.079 (3)	−0.0036 (16)	−0.0068 (19)	0.0200 (17)
C8	0.062 (3)	0.057 (2)	0.136 (5)	0.007 (2)	−0.012 (3)	0.028 (3)
C9	0.053 (3)	0.075 (3)	0.170 (6)	0.020 (2)	0.022 (3)	0.015 (3)
C10	0.062 (3)	0.068 (3)	0.111 (4)	0.003 (2)	0.038 (3)	0.004 (2)
C11	0.0454 (19)	0.0446 (17)	0.066 (2)	−0.0026 (15)	0.0159 (17)	0.0083 (16)
C12	0.0477 (19)	0.0370 (16)	0.057 (2)	−0.0010 (14)	0.0091 (15)	0.0119 (14)
C13	0.073 (3)	0.054 (2)	0.058 (2)	−0.0128 (18)	0.0226 (19)	0.0129 (17)
C14	0.099 (3)	0.054 (2)	0.058 (2)	0.008 (2)	−0.003 (2)	0.0214 (17)
C15	0.083 (3)	0.0477 (19)	0.0437 (19)	0.0127 (18)	−0.0020 (18)	0.0186 (15)
C16	0.082 (3)	0.060 (2)	0.059 (2)	−0.0055 (19)	0.014 (2)	0.0247 (18)
C17	0.080 (3)	0.056 (2)	0.051 (2)	0.0032 (19)	0.0152 (19)	0.0167 (16)
C18	0.062 (2)	0.0540 (19)	0.0415 (18)	0.0084 (16)	0.0002 (15)	0.0211 (15)
C19	0.067 (2)	0.080 (3)	0.061 (2)	0.007 (2)	0.0146 (19)	0.017 (2)
C20	0.080 (3)	0.072 (3)	0.060 (2)	0.009 (2)	0.012 (2)	0.004 (2)
C21	0.061 (2)	0.0471 (17)	0.0396 (17)	0.0028 (16)	0.0122 (15)	0.0141 (14)
C22	0.0561 (19)	0.0409 (16)	0.0446 (17)	0.0047 (14)	0.0108 (15)	0.0152 (13)
C23	0.073 (2)	0.053 (2)	0.051 (2)	0.0212 (17)	0.0210 (17)	0.0152 (16)
C24	0.069 (2)	0.062 (2)	0.055 (2)	0.0231 (18)	0.0075 (18)	0.0227 (17)
C25	0.064 (2)	0.055 (2)	0.0431 (18)	0.0007 (17)	0.0074 (16)	0.0192 (15)
C26	0.068 (2)	0.081 (3)	0.053 (2)	0.017 (2)	0.0235 (18)	0.0292 (19)
C27	0.057 (2)	0.083 (3)	0.057 (2)	0.0212 (19)	0.0184 (17)	0.0352 (19)
N4	0.080 (2)	0.087 (2)	0.052 (2)	0.0088 (19)	0.0094 (18)	0.0279 (17)
O5	0.115 (3)	0.171 (3)	0.0557 (18)	0.032 (2)	0.0289 (19)	0.043 (2)
O6	0.121 (3)	0.182 (4)	0.072 (2)	0.070 (3)	0.0121 (19)	0.062 (2)
S2	0.0732 (7)	0.1007 (8)	0.0565 (6)	0.0068 (6)	0.0234 (5)	0.0332 (5)
O1S	0.103 (2)	0.095 (2)	0.0608 (16)	0.0099 (16)	0.0414 (15)	0.0291 (14)
C1S	0.080 (3)	0.094 (3)	0.077 (3)	0.010 (2)	0.028 (2)	0.025 (2)
C2S	0.130 (4)	0.101 (4)	0.115 (4)	0.005 (3)	0.060 (3)	0.053 (3)

S1—O4	1.423 (3)	C15—C20	1.375 (5)
S1—O3	1.429 (2)	C15—C16	1.384 (5)
S1—N2	1.630 (3)	C16—C17	1.381 (5)
S1—C18	1.762 (3)	C16—H16	0.9300
N1—C2	1.388 (4)	C17—C18	1.383 (5)
N1—C13	1.394 (5)	C17—H17	0.9300
N1—C14	1.478 (4)	C18—C19	1.373 (5)
N2—N3	1.394 (3)	C19—C20	1.383 (5)
N2—H2N	0.8006	C19—H19	0.9300
N3—C21	1.263 (4)	C20—H20	0.9300
O1—C2	1.224 (4)	C21—C22	1.462 (4)
O2—C13	1.214 (4)	C21—H21	0.9300
C2—C3	1.461 (5)	C22—C23	1.383 (4)
C3—C4	1.377 (5)	C22—C27	1.394 (4)
C3—C12	1.404 (5)	C23—C24	1.381 (5)
C4—C5	1.380 (6)	C23—H23	0.9300
C4—H4	0.9300	C24—C25	1.367 (5)
C5—C6	1.336 (6)	C24—H24	0.9300
C5—H5	0.9300	C25—C26	1.369 (5)
C6—C7	1.415 (6)	C25—N4	1.474 (4)
C6—H6	0.9300	C26—C27	1.377 (5)
C7—C8	1.395 (6)	C26—H26	0.9300
C7—C12	1.418 (5)	C27—H27	0.9300
C8—C9	1.344 (7)	N4—O6	1.200 (4)
C8—H8	0.9300	N4—O5	1.213 (4)
C9—C10	1.391 (7)	S2—O1S	1.494 (3)
C9—H9	0.9300	S2—C1S	1.755 (4)
C10—C11	1.375 (5)	S2—C2S	1.781 (5)
C10—H10	0.9300	C1S—H1S1	0.9600
C11—C12	1.399 (5)	C1S—H1S2	0.9600
C11—C13	1.481 (5)	C1S—H1S3	0.9600
C14—C15	1.517 (5)	C2S—H2S1	0.9600
C14—H14A	0.9700	C2S—H2S2	0.9600
C14—H14B	0.9700	C2S—H2S3	0.9600
O4—S1—O3	120.25 (16)	C20—C15—C14	121.5 (4)
O4—S1—N2	108.61 (16)	C16—C15—C14	120.0 (4)
O3—S1—N2	103.64 (16)	C17—C16—C15	121.1 (4)
O4—S1—C18	107.94 (17)	C17—C16—H16	119.5
O3—S1—C18	109.03 (15)	C15—C16—H16	119.5
N2—S1—C18	106.58 (15)	C16—C17—C18	119.1 (4)
C2—N1—C13	123.8 (3)	C16—C17—H17	120.4
C2—N1—C14	118.4 (3)	C18—C17—H17	120.4
C13—N1—C14	117.7 (3)	C19—C18—C17	120.7 (3)
N3—N2—S1	115.3 (2)	C19—C18—S1	121.3 (3)
N3—N2—H2N	117.1	C17—C18—S1	118.0 (3)
S1—N2—H2N	114.1	C18—C19—C20	119.2 (4)
C21—N3—N2	115.5 (3)	C18—C19—H19	120.4
O1—C2—N1	119.3 (3)	C20—C19—H19	120.4
O1—C2—C3	122.8 (3)	C15—C20—C19	121.4 (4)
N1—C2—C3	117.9 (3)	C15—C20—H20	119.3
C4—C3—C12	119.4 (3)	C19—C20—H20	119.3
C4—C3—C2	120.4 (3)	N3—C21—C22	120.5 (3)
C12—C3—C2	120.1 (3)	N3—C21—H21	119.7
C3—C4—C5	120.8 (4)	C22—C21—H21	119.7
C3—C4—H4	119.6	C23—C22—C27	118.9 (3)
C5—C4—H4	119.6	C23—C22—C21	119.9 (3)
C6—C5—C4	121.3 (4)	C27—C22—C21	121.1 (3)
C6—C5—H5	119.4	C24—C23—C22	120.7 (3)
C4—C5—H5	119.4	C24—C23—H23	119.6
C5—C6—C7	120.7 (4)	C22—C23—H23	119.6
C5—C6—H6	119.6	C25—C24—C23	118.5 (3)
C7—C6—H6	119.6	C25—C24—H24	120.7
C8—C7—C6	124.0 (4)	C23—C24—H24	120.7
C8—C7—C12	117.6 (4)	C24—C25—C26	122.6 (3)
C6—C7—C12	118.3 (4)	C24—C25—N4	118.9 (3)
C9—C8—C7	121.7 (5)	C26—C25—N4	118.5 (3)
C9—C8—H8	119.1	C25—C26—C27	118.6 (3)
C7—C8—H8	119.1	C25—C26—H26	120.7
C8—C9—C10	120.9 (4)	C27—C26—H26	120.7
C8—C9—H9	119.6	C26—C27—C22	120.6 (3)
C10—C9—H9	119.6	C26—C27—H27	119.7
C11—C10—C9	119.9 (5)	C22—C27—H27	119.7
C11—C10—H10	120.1	O6—N4—O5	123.1 (4)
C9—C10—H10	120.1	O6—N4—C25	119.1 (4)
C10—C11—C12	119.8 (4)	O5—N4—C25	117.7 (4)
C10—C11—C13	120.2 (4)	O1S—S2—C1S	106.61 (19)
C12—C11—C13	119.9 (3)	O1S—S2—C2S	104.8 (2)
C11—C12—C3	120.5 (3)	C1S—S2—C2S	97.5 (2)
C11—C12—C7	120.1 (3)	S2—C1S—H1S1	109.5
C3—C12—C7	119.4 (3)	S2—C1S—H1S2	109.5
O2—C13—N1	120.1 (4)	H1S1—C1S—H1S2	109.5
O2—C13—C11	122.6 (4)	S2—C1S—H1S3	109.5
N1—C13—C11	117.3 (3)	H1S1—C1S—H1S3	109.5
N1—C14—C15	111.5 (3)	H1S2—C1S—H1S3	109.5
N1—C14—H14A	109.3	S2—C2S—H2S1	109.5
C15—C14—H14A	109.3	S2—C2S—H2S2	109.5
N1—C14—H14B	109.3	H2S1—C2S—H2S2	109.5
C15—C14—H14B	109.3	S2—C2S—H2S3	109.5
H14A—C14—H14B	108.0	H2S1—C2S—H2S3	109.5
C20—C15—C16	118.5 (3)	H2S2—C2S—H2S3	109.5
O4—S1—N2—N3	−49.9 (3)	C12—C11—C13—O2	176.2 (3)
O3—S1—N2—N3	−178.9 (2)	C10—C11—C13—N1	176.5 (3)
C18—S1—N2—N3	66.1 (3)	C12—C11—C13—N1	−4.8 (4)
S1—N2—N3—C21	−165.8 (2)	C2—N1—C14—C15	−96.1 (4)
C13—N1—C2—O1	−175.1 (3)	C13—N1—C14—C15	82.0 (4)
C14—N1—C2—O1	2.9 (5)	N1—C14—C15—C20	86.5 (5)
C13—N1—C2—C3	4.6 (5)	N1—C14—C15—C16	−92.5 (4)
C14—N1—C2—C3	−177.4 (3)	C20—C15—C16—C17	−2.3 (5)
O1—C2—C3—C4	−5.1 (6)	C14—C15—C16—C17	176.8 (3)
N1—C2—C3—C4	175.2 (3)	C15—C16—C17—C18	−0.1 (5)
O1—C2—C3—C12	172.8 (4)	C16—C17—C18—C19	2.1 (5)
N1—C2—C3—C12	−6.8 (5)	C16—C17—C18—S1	−176.1 (3)
C12—C3—C4—C5	0.2 (6)	O4—S1—C18—C19	5.1 (3)
C2—C3—C4—C5	178.1 (4)	O3—S1—C18—C19	137.3 (3)
C3—C4—C5—C6	−1.7 (7)	N2—S1—C18—C19	−111.5 (3)
C4—C5—C6—C7	1.1 (7)	O4—S1—C18—C17	−176.8 (3)
C5—C6—C7—C8	179.7 (4)	O3—S1—C18—C17	−44.6 (3)
C5—C6—C7—C12	0.8 (5)	N2—S1—C18—C17	66.7 (3)
C6—C7—C8—C9	−179.1 (4)	C17—C18—C19—C20	−1.6 (5)
C12—C7—C8—C9	−0.2 (6)	S1—C18—C19—C20	176.6 (3)
C7—C8—C9—C10	1.2 (7)	C16—C15—C20—C19	2.8 (6)
C8—C9—C10—C11	−1.2 (7)	C14—C15—C20—C19	−176.2 (3)
C9—C10—C11—C12	0.2 (5)	C18—C19—C20—C15	−0.9 (6)
C9—C10—C11—C13	179.0 (4)	N2—N3—C21—C22	−179.6 (2)
C10—C11—C12—C3	−178.8 (3)	N3—C21—C22—C23	−173.8 (3)
C13—C11—C12—C3	2.5 (4)	N3—C21—C22—C27	3.6 (5)
C10—C11—C12—C7	0.7 (5)	C27—C22—C23—C24	−2.0 (5)
C13—C11—C12—C7	−178.0 (3)	C21—C22—C23—C24	175.5 (3)
C4—C3—C12—C11	−178.7 (3)	C22—C23—C24—C25	0.7 (5)
C2—C3—C12—C11	3.3 (5)	C23—C24—C25—C26	0.3 (5)
C4—C3—C12—C7	1.8 (5)	C23—C24—C25—N4	−177.2 (3)
C2—C3—C12—C7	−176.2 (3)	C24—C25—C26—C27	−0.1 (5)
C8—C7—C12—C11	−0.7 (5)	N4—C25—C26—C27	177.5 (3)
C6—C7—C12—C11	178.2 (3)	C25—C26—C27—C22	−1.2 (5)
C8—C7—C12—C3	178.8 (3)	C23—C22—C27—C26	2.2 (5)
C6—C7—C12—C3	−2.3 (5)	C21—C22—C27—C26	−175.3 (3)
C2—N1—C13—O2	−179.9 (3)	C24—C25—N4—O6	−0.8 (5)
C14—N1—C13—O2	2.1 (5)	C26—C25—N4—O6	−178.5 (4)
C2—N1—C13—C11	1.1 (5)	C24—C25—N4—O5	177.4 (4)
C14—N1—C13—C11	−176.9 (3)	C26—C25—N4—O5	−0.3 (5)
C10—C11—C13—O2	−2.5 (5)

Cg is the centroid of the p-nitrophenyl (C22–C27) ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1S	0.80	1.99	2.764 (4)	163
C8—H8···Cgi	0.93	2.90	3.799 (6)	162

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the p-nitro­phenyl (C22–C27) ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1S	0.80	1.99	2.764 (4)	163
C8—H8⋯Cgi	0.93	2.90	3.799 (6)	162

Symmetry code: (i) .