7-Meth-oxy-1-{[(Z)-2-nitro-phenyl-imino](phen-yl)meth-yl}-2-naphthol chloro-form monosolvate.

In the title compound, C(24)H(18)N(2)O(4)·CHCl(3), the phenyl and benzene rings make a dihedral angle of 38.60 (9)° and connect in an orientation almost perpendicular to the naphthalene ring system at dihedral angles of 78.73 (8) and 81.20 (7)°. The mol-ecule has a Z configuration about the C=N bond. In the crystal, mol-ecules are linked by inter-molecular O-H⋯N=C hydrogen bonds between the imino moiety and hy-droxy groups. Inter-molecular C-Cl⋯C inter-actions between Cl atoms of the CHCl(3) mol-ecule and C atoms of the naphthalene rings are also present [Cl⋯C = 3.353 (2) and 3.326 (19) Å]. The nitro group and the chloro-form solvent mol-ecule are disordered over two positions with site occupancies of 0.884 (4) and 0.116 (4).

Related literature

For the structures of closely related compounds, see: Mitsui et al. (2008 ▶); Nagasawa et al. (2010a ▶,b ▶,c ▶,d ▶).

Experimental

Crystal data

C24H18N2O4·CHCl3

M = 517.77

Monoclinic,

a = 13.2672 (6) Å

b = 11.2865 (6) Å

c = 17.2371 (9) Å

β = 109.114 (1)°

V = 2438.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 193 K

0.60 × 0.30 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.762, T max = 0.960

38275 measured reflections

5576 independent reflections

4899 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.114

S = 1.06

5576 reflections

331 parameters

20 restraints

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.57 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810048002/pk2281sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048002/pk2281Isup2.hkl

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

C24H18N2O4·CHCl3	F(000) = 1064
Mr = 517.77	Dx = 1.410 Mg m−3
Monoclinic, P21/c	Melting point = 453.0–454.0 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71075 Å
a = 13.2672 (6) Å	Cell parameters from 30136 reflections
b = 11.2865 (6) Å	θ = 3.1–27.4°
c = 17.2371 (9) Å	µ = 0.41 mm−1
β = 109.114 (1)°	T = 193 K
V = 2438.8 (2) Å3	Platelet, colorless
Z = 4	0.60 × 0.30 × 0.10 mm

Rigaku R-AXIS RAPID diffractometer	5576 independent reflections
Radiation source: rotating anode	4899 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 10.00 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −17→17
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −14→14
Tmin = 0.762, Tmax = 0.960	l = −22→22
38275 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.056P)2 + 1.0227P] where P = (Fo2 + 2Fc2)/3
5576 reflections	(Δ/σ)max = 0.001
331 parameters	Δρmax = 0.50 e Å−3
20 restraints	Δρmin = −0.57 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	Occ. (<1)
O1	0.02083 (8)	0.05421 (9)	0.26338 (7)	0.0340 (2)
H1	0.0030	−0.0070	0.2736	0.051*
O2	0.43281 (10)	0.33884 (12)	0.13788 (8)	0.0460 (3)
N1	0.07278 (9)	0.34133 (10)	0.23258 (7)	0.0260 (2)
N2	0.2246 (4)	0.5366 (4)	0.28500 (16)	0.0388 (7)	0.884 (4)
O3	0.1947 (6)	0.5115 (6)	0.21267 (17)	0.0434 (6)	0.884 (4)
O4	0.2636 (3)	0.6325 (2)	0.31061 (13)	0.0886 (10)	0.884 (4)
N2'	0.227 (4)	0.522 (4)	0.2773 (13)	0.0388 (7)	0.116 (4)
O3'	0.198 (5)	0.518 (6)	0.2029 (15)	0.0434 (6)	0.116 (4)
O4'	0.3015 (11)	0.5866 (14)	0.3138 (9)	0.046 (3)*	0.116 (4)
C1	0.14869 (10)	0.14673 (11)	0.21739 (8)	0.0244 (3)
C2	0.11662 (11)	0.04855 (12)	0.25110 (8)	0.0284 (3)
C3	0.18235 (13)	−0.05341 (12)	0.27254 (9)	0.0357 (3)
H3	0.1592	−0.1208	0.2951	0.043*
C4	0.27910 (13)	−0.05430 (13)	0.26056 (9)	0.0369 (3)
H4	0.3223	−0.1233	0.2741	0.044*
C5	0.31622 (12)	0.04563 (13)	0.22843 (8)	0.0310 (3)
C6	0.41893 (13)	0.04875 (15)	0.21993 (9)	0.0391 (3)
H6	0.4636	−0.0190	0.2348	0.047*
C7	0.45494 (12)	0.14659 (17)	0.19098 (10)	0.0408 (4)
H7	0.5243	0.1470	0.1862	0.049*
C8	0.38870 (12)	0.24785 (14)	0.16805 (9)	0.0344 (3)
C9	0.28882 (11)	0.24960 (12)	0.17571 (8)	0.0279 (3)
H9	0.2454	0.3182	0.1604	0.033*
C10	0.25066 (11)	0.14845 (11)	0.20667 (8)	0.0255 (3)
C11	0.07401 (10)	0.24982 (11)	0.18894 (8)	0.0237 (2)
C12	0.00079 (11)	0.25001 (12)	0.10229 (8)	0.0269 (3)
C13	−0.03252 (13)	0.14463 (13)	0.05936 (9)	0.0361 (3)
H13	−0.0093	0.0708	0.0856	0.043*
C14	−0.09970 (15)	0.14713 (16)	−0.02191 (10)	0.0442 (4)
H14	−0.1230	0.0749	−0.0505	0.053*
C15	−0.13261 (14)	0.25356 (17)	−0.06123 (10)	0.0458 (4)
H15	−0.1778	0.2546	−0.1169	0.055*
C16	−0.09974 (16)	0.35897 (16)	−0.01956 (10)	0.0473 (4)
H16	−0.1225	0.4324	−0.0466	0.057*
C17	−0.03340 (14)	0.35763 (13)	0.06198 (9)	0.0380 (3)
H17	−0.0112	0.4302	0.0904	0.046*
C18	0.13766 (11)	0.35278 (12)	0.31576 (8)	0.0268 (3)
C19	0.12082 (13)	0.27964 (13)	0.37559 (9)	0.0338 (3)
H19	0.0736	0.2141	0.3595	0.041*
C20	0.17225 (14)	0.30158 (15)	0.45846 (9)	0.0399 (4)
H20	0.1600	0.2508	0.4984	0.048*
C21	0.24114 (14)	0.39668 (15)	0.48345 (9)	0.0418 (4)
H21	0.2768	0.4103	0.5402	0.050*
C22	0.25782 (13)	0.47152 (15)	0.42562 (9)	0.0396 (3)
H22	0.3043	0.5376	0.4424	0.047*
C23	0.20625 (12)	0.44975 (13)	0.34255 (9)	0.0312 (3)
C24	0.36876 (16)	0.44165 (17)	0.10900 (12)	0.0506 (4)
H24A	0.4090	0.4993	0.0884	0.076*
H24B	0.3495	0.4769	0.1542	0.076*
H24C	0.3038	0.4192	0.0646	0.076*
C25	0.4954 (2)	0.2617 (3)	0.4771 (2)	0.0463 (5)	0.884 (4)
H2	0.4638	0.2954	0.5176	0.056*	0.884 (4)
Cl1	0.51726 (10)	0.38033 (11)	0.41735 (8)	0.0718 (3)	0.884 (4)
Cl2	0.40495 (10)	0.15916 (14)	0.41674 (8)	0.0602 (3)	0.884 (4)
Cl3	0.61723 (8)	0.19467 (8)	0.53272 (8)	0.0620 (3)	0.884 (4)
C25'	0.5097 (15)	0.2618 (19)	0.4821 (15)	0.0463 (5)	0.116 (4)
H2'	0.4931	0.3008	0.5285	0.056*	0.116 (4)
Cl1'	0.4895 (8)	0.3540 (8)	0.3952 (6)	0.0718 (3)	0.116 (4)
Cl2'	0.4217 (9)	0.1492 (13)	0.4346 (7)	0.0602 (3)	0.116 (4)
Cl3'	0.6378 (6)	0.2033 (7)	0.5088 (5)	0.0620 (3)	0.116 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0372 (5)	0.0222 (5)	0.0436 (6)	−0.0058 (4)	0.0145 (4)	0.0038 (4)
O2	0.0392 (6)	0.0544 (7)	0.0499 (7)	−0.0097 (5)	0.0220 (5)	0.0005 (6)
N1	0.0309 (6)	0.0215 (5)	0.0245 (5)	0.0023 (4)	0.0073 (4)	0.0010 (4)
N2	0.0458 (8)	0.0336 (15)	0.0359 (8)	−0.0118 (11)	0.0118 (8)	−0.0040 (8)
O3	0.0662 (10)	0.0354 (11)	0.0318 (10)	−0.0064 (7)	0.0205 (12)	0.0025 (12)
O4	0.150 (3)	0.0520 (13)	0.0558 (11)	−0.0610 (16)	0.0229 (13)	−0.0100 (10)
N2'	0.0458 (8)	0.0336 (15)	0.0359 (8)	−0.0118 (11)	0.0118 (8)	−0.0040 (8)
O3'	0.0662 (10)	0.0354 (11)	0.0318 (10)	−0.0064 (7)	0.0205 (12)	0.0025 (12)
C1	0.0297 (6)	0.0191 (6)	0.0222 (6)	0.0007 (5)	0.0056 (5)	−0.0010 (4)
C2	0.0347 (7)	0.0210 (6)	0.0273 (6)	−0.0021 (5)	0.0072 (5)	−0.0005 (5)
C3	0.0485 (8)	0.0208 (6)	0.0347 (7)	0.0024 (6)	0.0095 (6)	0.0050 (5)
C4	0.0473 (8)	0.0263 (7)	0.0326 (7)	0.0121 (6)	0.0070 (6)	0.0028 (6)
C5	0.0354 (7)	0.0314 (7)	0.0232 (6)	0.0076 (6)	0.0054 (5)	−0.0026 (5)
C6	0.0362 (8)	0.0468 (9)	0.0312 (7)	0.0144 (7)	0.0070 (6)	−0.0022 (6)
C7	0.0295 (7)	0.0583 (10)	0.0343 (8)	0.0050 (7)	0.0099 (6)	−0.0063 (7)
C8	0.0338 (7)	0.0427 (8)	0.0271 (7)	−0.0055 (6)	0.0103 (6)	−0.0054 (6)
C9	0.0303 (6)	0.0286 (7)	0.0239 (6)	−0.0006 (5)	0.0077 (5)	−0.0027 (5)
C10	0.0300 (6)	0.0254 (6)	0.0188 (5)	0.0018 (5)	0.0048 (5)	−0.0028 (5)
C11	0.0263 (6)	0.0197 (6)	0.0254 (6)	−0.0012 (5)	0.0090 (5)	0.0018 (5)
C12	0.0285 (6)	0.0263 (6)	0.0249 (6)	0.0002 (5)	0.0074 (5)	0.0006 (5)
C13	0.0449 (8)	0.0281 (7)	0.0309 (7)	−0.0040 (6)	0.0066 (6)	−0.0008 (6)
C14	0.0521 (10)	0.0415 (9)	0.0323 (8)	−0.0111 (7)	0.0047 (7)	−0.0083 (7)
C15	0.0468 (9)	0.0559 (10)	0.0263 (7)	−0.0031 (8)	0.0005 (6)	0.0005 (7)
C16	0.0598 (11)	0.0414 (9)	0.0316 (8)	0.0084 (8)	0.0024 (7)	0.0088 (7)
C17	0.0505 (9)	0.0284 (7)	0.0295 (7)	0.0035 (6)	0.0057 (6)	0.0012 (6)
C18	0.0305 (6)	0.0241 (6)	0.0245 (6)	0.0051 (5)	0.0072 (5)	−0.0012 (5)
C19	0.0439 (8)	0.0267 (7)	0.0307 (7)	0.0011 (6)	0.0122 (6)	0.0006 (5)
C20	0.0564 (10)	0.0363 (8)	0.0274 (7)	0.0086 (7)	0.0141 (7)	0.0059 (6)
C21	0.0511 (9)	0.0434 (9)	0.0237 (7)	0.0078 (7)	0.0026 (6)	−0.0029 (6)
C22	0.0409 (8)	0.0378 (8)	0.0328 (8)	−0.0019 (6)	0.0023 (6)	−0.0059 (6)
C23	0.0341 (7)	0.0294 (7)	0.0282 (7)	0.0001 (5)	0.0077 (5)	0.0001 (5)
C24	0.0516 (10)	0.0490 (10)	0.0549 (10)	−0.0131 (8)	0.0225 (8)	0.0076 (8)
C25	0.0548 (12)	0.0498 (10)	0.0337 (9)	−0.0049 (9)	0.0137 (9)	−0.0057 (7)
Cl1	0.0736 (6)	0.0777 (5)	0.0555 (5)	−0.0211 (4)	0.0093 (4)	0.0162 (4)
Cl2	0.0497 (5)	0.0729 (5)	0.0506 (6)	−0.0098 (4)	0.0065 (4)	−0.0209 (5)
Cl3	0.0576 (4)	0.0652 (4)	0.0514 (5)	−0.0027 (3)	0.0017 (3)	−0.0042 (3)
C25'	0.0548 (12)	0.0498 (10)	0.0337 (9)	−0.0049 (9)	0.0137 (9)	−0.0057 (7)
Cl1'	0.0736 (6)	0.0777 (5)	0.0555 (5)	−0.0211 (4)	0.0093 (4)	0.0162 (4)
Cl2'	0.0497 (5)	0.0729 (5)	0.0506 (6)	−0.0098 (4)	0.0065 (4)	−0.0209 (5)
Cl3'	0.0576 (4)	0.0652 (4)	0.0514 (5)	−0.0027 (3)	0.0017 (3)	−0.0042 (3)

O1—C2	1.3566 (18)	C12—C17	1.399 (2)
O1—H1	0.7695	C13—C14	1.393 (2)
O2—C8	1.3664 (19)	C13—H13	0.9500
O2—C24	1.428 (2)	C14—C15	1.378 (3)
N1—C11	1.2810 (17)	C14—H14	0.9500
N1—C18	1.4159 (17)	C15—C16	1.384 (3)
N2—O3	1.211 (3)	C15—H15	0.9500
N2—O4	1.219 (3)	C16—C17	1.393 (2)
N2—C23	1.470 (3)	C16—H16	0.9500
N2'—O3'	1.214 (17)	C17—H17	0.9500
N2'—O4'	1.230 (18)	C18—C19	1.395 (2)
N2'—C23	1.481 (17)	C18—C23	1.401 (2)
C1—C2	1.3814 (18)	C19—C20	1.389 (2)
C1—C10	1.4242 (18)	C19—H19	0.9500
C1—C11	1.5026 (17)	C20—C21	1.384 (3)
C2—C3	1.4178 (19)	C20—H20	0.9500
C3—C4	1.365 (2)	C21—C22	1.379 (2)
C3—H3	0.9500	C21—H21	0.9500
C4—C5	1.414 (2)	C22—C23	1.392 (2)
C4—H4	0.9500	C22—H22	0.9500
C5—C6	1.418 (2)	C24—H24A	0.9800
C5—C10	1.4249 (18)	C24—H24B	0.9800
C6—C7	1.361 (3)	C24—H24C	0.9800
C6—H6	0.9500	C25—Cl2	1.745 (3)
C7—C8	1.417 (2)	C25—Cl3	1.757 (3)
C7—H7	0.9500	C25—Cl1	1.770 (3)
C8—C9	1.374 (2)	C25—H2	1.0000
C9—C10	1.4217 (19)	C25'—Cl3'	1.739 (19)
C9—H9	0.9500	C25'—Cl2'	1.740 (18)
C11—C12	1.4915 (18)	C25'—Cl1'	1.770 (19)
C12—C13	1.394 (2)	C25'—H2'	1.0000
C2—O1—H1	111.6	C15—C14—H14	119.7
C8—O2—C24	117.60 (13)	C13—C14—H14	119.7
C11—N1—C18	123.21 (11)	C14—C15—C16	119.91 (14)
O3—N2—O4	122.5 (4)	C14—C15—H15	120.0
O3—N2—C23	117.9 (3)	C16—C15—H15	120.0
O4—N2—C23	119.5 (2)	C15—C16—C17	120.12 (15)
O3'—N2'—O4'	119 (3)	C15—C16—H16	119.9
O3'—N2'—C23	135 (3)	C17—C16—H16	119.9
O4'—N2'—C23	104.8 (17)	C16—C17—C12	120.37 (14)
C2—C1—C10	120.13 (12)	C16—C17—H17	119.8
C2—C1—C11	119.83 (12)	C12—C17—H17	119.8
C10—C1—C11	120.00 (11)	C19—C18—C23	117.54 (12)
O1—C2—C1	117.46 (12)	C19—C18—N1	120.21 (12)
O1—C2—C3	121.68 (12)	C23—C18—N1	121.25 (12)
C1—C2—C3	120.86 (13)	C20—C19—C18	120.74 (14)
C4—C3—C2	119.67 (13)	C20—C19—H19	119.6
C4—C3—H3	120.2	C18—C19—H19	119.6
C2—C3—H3	120.2	C21—C20—C19	120.69 (14)
C3—C4—C5	121.24 (13)	C21—C20—H20	119.7
C3—C4—H4	119.4	C19—C20—H20	119.7
C5—C4—H4	119.4	C22—C21—C20	119.75 (14)
C4—C5—C6	122.01 (13)	C22—C21—H21	120.1
C4—C5—C10	119.46 (13)	C20—C21—H21	120.1
C6—C5—C10	118.49 (14)	C21—C22—C23	119.63 (15)
C7—C6—C5	121.51 (14)	C21—C22—H22	120.2
C7—C6—H6	119.2	C23—C22—H22	120.2
C5—C6—H6	119.2	C22—C23—C18	121.62 (14)
C6—C7—C8	119.77 (14)	C22—C23—N2	116.26 (16)
C6—C7—H7	120.1	C18—C23—N2	122.07 (15)
C8—C7—H7	120.1	C22—C23—N2'	122.3 (9)
O2—C8—C9	124.92 (14)	C18—C23—N2'	115.9 (9)
O2—C8—C7	114.12 (14)	O2—C24—H24A	109.5
C9—C8—C7	120.96 (14)	O2—C24—H24B	109.5
C8—C9—C10	119.84 (13)	H24A—C24—H24B	109.5
C8—C9—H9	120.1	O2—C24—H24C	109.5
C10—C9—H9	120.1	H24A—C24—H24C	109.5
C9—C10—C1	121.99 (12)	H24B—C24—H24C	109.5
C9—C10—C5	119.41 (13)	Cl2—C25—Cl3	111.70 (19)
C1—C10—C5	118.60 (12)	Cl2—C25—Cl1	111.47 (19)
N1—C11—C12	117.23 (11)	Cl3—C25—Cl1	110.27 (16)
N1—C11—C1	124.51 (12)	Cl2—C25—H2	107.7
C12—C11—C1	118.13 (11)	Cl3—C25—H2	107.7
C13—C12—C17	118.83 (13)	Cl1—C25—H2	107.7
C13—C12—C11	121.31 (12)	Cl3'—C25'—Cl2'	107.2 (13)
C17—C12—C11	119.83 (12)	Cl3'—C25'—Cl1'	108.2 (13)
C14—C13—C12	120.25 (14)	Cl2'—C25'—Cl1'	98.0 (12)
C14—C13—H13	119.9	Cl3'—C25'—H2'	114.1
C12—C13—H13	119.9	Cl2'—C25'—H2'	114.1
C15—C14—C13	120.51 (15)	Cl1'—C25'—H2'	114.1
C10—C1—C2—O1	176.96 (11)	C1—C11—C12—C17	−151.40 (14)
C11—C1—C2—O1	−5.47 (18)	C17—C12—C13—C14	−0.8 (2)
C10—C1—C2—C3	−2.5 (2)	C11—C12—C13—C14	−179.07 (14)
C11—C1—C2—C3	175.10 (12)	C12—C13—C14—C15	1.1 (3)
O1—C2—C3—C4	−178.72 (13)	C13—C14—C15—C16	−0.7 (3)
C1—C2—C3—C4	0.7 (2)	C14—C15—C16—C17	0.1 (3)
C2—C3—C4—C5	1.2 (2)	C15—C16—C17—C12	0.2 (3)
C3—C4—C5—C6	176.36 (14)	C13—C12—C17—C16	0.2 (2)
C3—C4—C5—C10	−1.2 (2)	C11—C12—C17—C16	178.47 (15)
C4—C5—C6—C7	−178.21 (14)	C11—N1—C18—C19	−66.99 (18)
C10—C5—C6—C7	−0.6 (2)	C11—N1—C18—C23	124.71 (15)
C5—C6—C7—C8	−0.5 (2)	C23—C18—C19—C20	−1.3 (2)
C24—O2—C8—C9	−2.7 (2)	N1—C18—C19—C20	−170.00 (13)
C24—O2—C8—C7	176.52 (14)	C18—C19—C20—C21	0.2 (2)
C6—C7—C8—O2	−178.28 (14)	C19—C20—C21—C22	0.9 (3)
C6—C7—C8—C9	1.0 (2)	C20—C21—C22—C23	−0.9 (2)
O2—C8—C9—C10	178.85 (13)	C21—C22—C23—C18	−0.3 (2)
C7—C8—C9—C10	−0.3 (2)	C21—C22—C23—N2	177.4 (3)
C8—C9—C10—C1	178.66 (12)	C21—C22—C23—N2'	−176 (3)
C8—C9—C10—C5	−0.81 (19)	C19—C18—C23—C22	1.4 (2)
C2—C1—C10—C9	−177.09 (12)	N1—C18—C23—C22	169.96 (13)
C11—C1—C10—C9	5.34 (18)	C19—C18—C23—N2	−176.2 (3)
C2—C1—C10—C5	2.38 (18)	N1—C18—C23—N2	−7.6 (3)
C11—C1—C10—C5	−175.19 (11)	C19—C18—C23—N2'	177 (3)
C4—C5—C10—C9	178.91 (12)	N1—C18—C23—N2'	−14 (3)
C6—C5—C10—C9	1.27 (19)	O3—N2—C23—C22	168.9 (6)
C4—C5—C10—C1	−0.57 (19)	O4—N2—C23—C22	−14.9 (6)
C6—C5—C10—C1	−178.22 (12)	O3—N2—C23—C18	−13.4 (8)
C18—N1—C11—C12	179.69 (12)	O4—N2—C23—C18	162.8 (4)
C18—N1—C11—C1	−4.4 (2)	O3—N2—C23—N2'	33 (12)
C2—C1—C11—N1	94.25 (16)	O4—N2—C23—N2'	−151 (13)
C10—C1—C11—N1	−88.17 (16)	O3'—N2'—C23—C22	175 (7)
C2—C1—C11—C12	−89.89 (15)	O4'—N2'—C23—C22	7(5)
C10—C1—C11—C12	87.69 (15)	O3'—N2'—C23—C18	0(9)
N1—C11—C12—C13	−156.96 (14)	O4'—N2'—C23—C18	−168 (2)
C1—C11—C12—C13	26.88 (19)	O3'—N2'—C23—N2	−137 (20)
N1—C11—C12—C17	24.77 (19)	O4'—N2'—C23—N2	55 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.77	1.97	2.7160 (16)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.77	1.97	2.7160 (16)	163

Symmetry code: (i) .