1-{2-(4-Chloro-benz-yloxy)-2-[4-(mor-pho-lin-4-yl)phen-yl]eth-yl}-1H-benzimidazole propan-2-ol monosolvate.

In the title compound, C26H26ClN3O2·C3H7OH, the benzimid-azole ring system is essentially planar [maximum deviation = -0.018 (2) Å] and its mean plane is oriented with respect to the two benzene rings at dihedral angles of 4.51 (6) and 56.16 (6)°, and the dihedral angle between the two benzene rings is 59.11 (7)°. The morpholine ring displays a chair conformation. The propan-2-ol solvent mol-ecule links with the benzimidazole ring via an O-H⋯N hydrogen bond. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into inversion dimers with an R 2 (2)(28) motif. π-π stacking occurs between the parallel chloro-benzene rings [centroid-centroid distance = 3.792 (1) Å]. Weak C-H⋯π inter-actions and short Cl⋯Cl [3.2037 (10) Å] contacts are also observed.

Related literature

For general background to the biological activity of benz­imid­azole derivatives, see: Özel Güven et al. (2007a ▶,b ▶). For related structures, see: Caira et al. (2004 ▶); Freer et al. (1986 ▶); Özel Güven et al. (2008a ▶,b ▶,c ▶,d ▶, 2013 ▶); Peeters et al. (1979a ▶,b ▶, 1996 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For ring motif details, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C26H26ClN3O2·C3H8O

M = 508.04

Triclinic,

a = 10.6542 (3) Å

b = 11.5152 (4) Å

c = 11.6853 (4) Å

α = 87.010 (3)°

β = 83.703 (3)°

γ = 71.572 (2)°

V = 1351.66 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.18 mm−1

T = 294 K

0.30 × 0.28 × 0.25 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer

Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011 ▶) T min = 0.95, T max = 0.96

17368 measured reflections

6139 independent reflections

3561 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.186

S = 1.11

6139 reflections

332 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.53 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku, 2011 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813022599/xu5728sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813022599/xu5728Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813022599/xu5728Isup3.cml

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

C26H26ClN3O2·C3H8O	Z = 2
Mr = 508.04	F(000) = 540
Triclinic, P1	Dx = 1.248 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.6542 (3) Å	Cell parameters from 10744 reflections
b = 11.5152 (4) Å	θ = 3.0–27.4°
c = 11.6853 (4) Å	µ = 0.18 mm−1
α = 87.010 (3)°	T = 294 K
β = 83.703 (3)°	Prism, colorless
γ = 71.572 (2)°	0.30 × 0.28 × 0.25 mm
V = 1351.66 (8) Å3

Rigaku R-AXIS RAPID-S diffractometer	6139 independent reflections
Radiation source: fine-focus sealed tube	3561 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011)	h = −13→13
Tmin = 0.95, Tmax = 0.96	k = −14→14
17368 measured reflections	l = −14→15

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)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.186	w = 1/[σ2(Fo2) + (0.093P)2] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
6139 reflections	Δρmax = 0.50 e Å−3
332 parameters	Δρmin = −0.53 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.010 (3)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl1	0.12222 (6)	0.01131 (6)	0.06222 (7)	0.0564 (3)
O1	0.55011 (15)	0.28048 (12)	0.19797 (12)	0.0332 (4)
O2	1.05293 (17)	0.58050 (15)	−0.36418 (15)	0.0478 (5)
O3	0.73878 (19)	0.85398 (16)	0.32068 (16)	0.0496 (5)
H3A	0.699 (3)	0.816 (3)	0.368 (2)	0.086 (12)*
N1	0.55093 (18)	0.35870 (15)	0.42231 (14)	0.0296 (4)
N2	0.41749 (19)	0.27808 (17)	0.53940 (16)	0.0364 (5)
N3	0.90888 (18)	0.48375 (15)	−0.18415 (15)	0.0313 (4)
C1	0.6596 (2)	0.31728 (19)	0.22470 (18)	0.0308 (5)
H1	0.7254	0.2463	0.2565	0.037*
C2	0.6021 (2)	0.41068 (19)	0.31857 (18)	0.0317 (5)
H2A	0.6705	0.4436	0.3373	0.038*
H2B	0.5308	0.4777	0.2902	0.038*
C3	0.4401 (2)	0.32288 (19)	0.4366 (2)	0.0337 (5)
H3	0.3851	0.3296	0.3785	0.040*
C4	0.6061 (2)	0.33516 (18)	0.52643 (18)	0.0299 (5)
C5	0.7173 (2)	0.35401 (19)	0.56430 (19)	0.0357 (5)
H5	0.7736	0.3863	0.5157	0.043*
C6	0.7403 (3)	0.3225 (2)	0.6777 (2)	0.0433 (6)
H6	0.8127	0.3352	0.7066	0.052*
C7	0.6563 (3)	0.2716 (2)	0.7504 (2)	0.0462 (7)
H7	0.6750	0.2508	0.8260	0.055*
C8	0.5472 (3)	0.2517 (2)	0.7123 (2)	0.0413 (6)
H8	0.4926	0.2174	0.7608	0.050*
C9	0.5211 (2)	0.28481 (18)	0.59858 (19)	0.0328 (5)
C10	0.5907 (3)	0.1737 (2)	0.1282 (2)	0.0419 (6)
H10A	0.6551	0.1073	0.1652	0.050*
H10B	0.6318	0.1911	0.0538	0.050*
C11	0.4708 (2)	0.13819 (19)	0.1133 (2)	0.0343 (5)
C12	0.4139 (2)	0.0811 (2)	0.2031 (2)	0.0376 (6)
H12	0.4498	0.0671	0.2735	0.045*
C13	0.3050 (2)	0.0453 (2)	0.1886 (2)	0.0398 (6)
H13	0.2670	0.0078	0.2490	0.048*
C14	0.2527 (2)	0.0656 (2)	0.0829 (2)	0.0389 (6)
C15	0.3053 (3)	0.1241 (2)	−0.0070 (2)	0.0406 (6)
H15	0.2691	0.1383	−0.0772	0.049*
C16	0.4130 (3)	0.1608 (2)	0.0104 (2)	0.0389 (6)
H16	0.4480	0.2020	−0.0489	0.047*
C17	0.7259 (2)	0.36472 (18)	0.12031 (18)	0.0301 (5)
C18	0.8556 (2)	0.30403 (19)	0.07960 (19)	0.0349 (5)
H18	0.9027	0.2344	0.1190	0.042*
C19	0.9176 (2)	0.3435 (2)	−0.0178 (2)	0.0372 (6)
H19	1.0055	0.3004	−0.0419	0.045*
C20	0.8508 (2)	0.44694 (18)	−0.08082 (18)	0.0297 (5)
C21	0.7187 (2)	0.5080 (2)	−0.0392 (2)	0.0368 (6)
H21	0.6704	0.5769	−0.0789	0.044*
C22	0.6590 (2)	0.4684 (2)	0.0586 (2)	0.0376 (6)
H22	0.5718	0.5119	0.0843	0.045*
C23	1.0515 (2)	0.4257 (2)	−0.2155 (2)	0.0358 (6)
H23A	1.0739	0.3379	−0.2027	0.043*
H23B	1.1021	0.4564	−0.1674	0.043*
C24	1.0869 (3)	0.4525 (2)	−0.3397 (2)	0.0434 (6)
H24A	1.1817	0.4149	−0.3589	0.052*
H24B	1.0408	0.4165	−0.3876	0.052*
C25	0.9129 (3)	0.6344 (2)	−0.3385 (2)	0.0512 (7)
H25A	0.8669	0.5993	−0.3874	0.061*
H25B	0.8889	0.7216	−0.3555	0.061*
C26	0.8684 (2)	0.6145 (2)	−0.2142 (2)	0.0405 (6)
H26A	0.9071	0.6566	−0.1652	0.049*
H26B	0.7724	0.6485	−0.2012	0.049*
C27	0.8136 (3)	0.8985 (2)	0.3906 (2)	0.0507 (7)
H27	0.8611	0.8314	0.4402	0.061*
C28	0.7247 (4)	1.0008 (3)	0.4653 (3)	0.0780 (11)
H28A	0.6592	0.9727	0.5113	0.117*
H28B	0.6810	1.0687	0.4175	0.117*
H28C	0.7770	1.0261	0.5148	0.117*
C29	0.9145 (3)	0.9384 (3)	0.3103 (3)	0.0661 (9)
H29A	0.9703	0.8700	0.2660	0.099*
H29B	0.9681	0.9684	0.3546	0.099*
H29C	0.8690	1.0023	0.2594	0.099*

	U11	U22	U33	U12	U13	U23
Cl1	0.0380 (4)	0.0487 (4)	0.0835 (6)	−0.0127 (3)	−0.0057 (4)	−0.0166 (4)
O1	0.0351 (9)	0.0301 (8)	0.0351 (9)	−0.0117 (7)	0.0014 (7)	−0.0076 (6)
O2	0.0428 (11)	0.0463 (10)	0.0497 (11)	−0.0139 (8)	0.0105 (8)	0.0080 (8)
O3	0.0585 (13)	0.0505 (11)	0.0468 (11)	−0.0286 (9)	0.0008 (9)	−0.0029 (9)
N1	0.0369 (11)	0.0313 (9)	0.0229 (9)	−0.0140 (8)	−0.0027 (8)	−0.0003 (7)
N2	0.0369 (12)	0.0379 (10)	0.0370 (11)	−0.0162 (9)	0.0005 (9)	−0.0032 (8)
N3	0.0332 (11)	0.0306 (9)	0.0286 (10)	−0.0086 (8)	0.0002 (8)	−0.0013 (8)
C1	0.0350 (13)	0.0272 (11)	0.0310 (12)	−0.0113 (9)	−0.0026 (10)	0.0000 (9)
C2	0.0381 (13)	0.0316 (11)	0.0278 (11)	−0.0151 (10)	−0.0018 (10)	0.0022 (9)
C3	0.0336 (13)	0.0366 (12)	0.0348 (12)	−0.0174 (10)	−0.0008 (10)	−0.0003 (10)
C4	0.0360 (13)	0.0231 (10)	0.0312 (12)	−0.0100 (9)	−0.0019 (10)	−0.0048 (9)
C5	0.0428 (14)	0.0311 (12)	0.0350 (13)	−0.0139 (10)	−0.0036 (11)	−0.0024 (10)
C6	0.0534 (16)	0.0402 (13)	0.0407 (14)	−0.0187 (12)	−0.0123 (12)	0.0009 (11)
C7	0.0681 (19)	0.0421 (14)	0.0314 (13)	−0.0194 (13)	−0.0130 (12)	0.0045 (11)
C8	0.0579 (17)	0.0337 (12)	0.0325 (13)	−0.0168 (11)	0.0015 (12)	0.0021 (10)
C9	0.0423 (14)	0.0252 (10)	0.0308 (12)	−0.0125 (10)	0.0035 (10)	−0.0018 (9)
C10	0.0459 (15)	0.0383 (13)	0.0435 (14)	−0.0165 (11)	0.0041 (12)	−0.0146 (11)
C11	0.0410 (14)	0.0254 (11)	0.0375 (13)	−0.0122 (9)	0.0005 (11)	−0.0078 (9)
C12	0.0474 (15)	0.0323 (12)	0.0316 (12)	−0.0114 (10)	−0.0006 (11)	−0.0015 (10)
C13	0.0426 (15)	0.0296 (12)	0.0463 (15)	−0.0123 (10)	0.0022 (12)	0.0001 (10)
C14	0.0363 (14)	0.0279 (11)	0.0492 (15)	−0.0051 (10)	−0.0028 (11)	−0.0071 (10)
C15	0.0503 (16)	0.0302 (12)	0.0367 (14)	−0.0041 (11)	−0.0081 (12)	−0.0045 (10)
C16	0.0520 (16)	0.0299 (12)	0.0349 (13)	−0.0139 (11)	0.0010 (11)	−0.0056 (10)
C17	0.0379 (13)	0.0252 (10)	0.0292 (11)	−0.0125 (9)	−0.0045 (10)	−0.0007 (9)
C18	0.0381 (14)	0.0286 (11)	0.0342 (12)	−0.0068 (10)	−0.0013 (10)	0.0052 (9)
C19	0.0308 (13)	0.0344 (12)	0.0405 (13)	−0.0033 (10)	0.0010 (10)	−0.0001 (10)
C20	0.0344 (13)	0.0270 (10)	0.0298 (11)	−0.0116 (9)	−0.0048 (10)	−0.0022 (9)
C21	0.0377 (14)	0.0305 (11)	0.0348 (13)	−0.0028 (10)	0.0016 (10)	0.0044 (10)
C22	0.0341 (13)	0.0327 (12)	0.0392 (13)	−0.0033 (10)	0.0037 (11)	0.0014 (10)
C23	0.0334 (13)	0.0314 (11)	0.0410 (13)	−0.0102 (10)	0.0049 (11)	−0.0033 (10)
C24	0.0434 (15)	0.0435 (14)	0.0414 (14)	−0.0147 (11)	0.0095 (12)	−0.0052 (11)
C25	0.0427 (16)	0.0558 (16)	0.0449 (15)	−0.0063 (12)	0.0032 (12)	0.0159 (13)
C26	0.0395 (14)	0.0363 (13)	0.0390 (14)	−0.0063 (10)	0.0042 (11)	0.0071 (10)
C27	0.0587 (18)	0.0490 (15)	0.0509 (16)	−0.0259 (13)	−0.0093 (14)	0.0071 (13)
C28	0.112 (3)	0.073 (2)	0.060 (2)	−0.050 (2)	0.0162 (19)	−0.0216 (17)
C29	0.0525 (19)	0.0605 (18)	0.089 (2)	−0.0247 (15)	−0.0039 (17)	0.0047 (16)

Cl1—C14	1.738 (3)	C14—C15	1.381 (3)
O1—C1	1.430 (3)	C14—C13	1.389 (4)
O1—C10	1.433 (2)	C15—C16	1.380 (3)
O2—C24	1.424 (3)	C15—H15	0.9300
O2—C25	1.427 (3)	C16—C11	1.386 (3)
O3—C27	1.418 (3)	C16—H16	0.9300
O3—H3A	0.847 (18)	C17—C1	1.507 (3)
N1—C2	1.453 (3)	C17—C18	1.379 (3)
N1—C3	1.360 (3)	C17—C22	1.392 (3)
N1—C4	1.386 (3)	C18—H18	0.9300
N2—C3	1.310 (3)	C19—C18	1.382 (3)
N2—C9	1.389 (3)	C19—C20	1.398 (3)
N3—C20	1.403 (3)	C19—H19	0.9300
N3—C23	1.466 (3)	C20—C21	1.404 (3)
N3—C26	1.464 (3)	C21—H21	0.9300
C1—C2	1.515 (3)	C22—C21	1.375 (3)
C1—H1	0.9800	C22—H22	0.9300
C2—H2A	0.9700	C23—C24	1.500 (3)
C2—H2B	0.9700	C23—H23A	0.9700
C3—H3	0.9300	C23—H23B	0.9700
C4—C5	1.391 (3)	C24—H24A	0.9700
C4—C9	1.407 (3)	C24—H24B	0.9700
C5—C6	1.383 (3)	C25—H25A	0.9700
C5—H5	0.9300	C25—H25B	0.9700
C6—H6	0.9300	C26—C25	1.507 (3)
C7—C6	1.406 (3)	C26—H26A	0.9700
C7—H7	0.9300	C26—H26B	0.9700
C8—C7	1.376 (4)	C27—C28	1.506 (4)
C8—H8	0.9300	C27—C29	1.514 (4)
C9—C8	1.397 (3)	C27—H27	0.9800
C10—H10A	0.9700	C28—H28A	0.9600
C10—H10B	0.9700	C28—H28B	0.9600
C11—C10	1.489 (3)	C28—H28C	0.9600
C12—C11	1.394 (3)	C29—H29A	0.9600
C12—C13	1.378 (3)	C29—H29B	0.9600
C12—H12	0.9300	C29—H29C	0.9600
C13—H13	0.9300
C1—O1—C10	112.78 (16)	C11—C16—H16	119.0
C24—O2—C25	108.72 (18)	C15—C16—C11	122.1 (2)
C27—O3—H3A	103 (2)	C15—C16—H16	119.0
C3—N1—C2	127.01 (18)	C18—C17—C1	120.85 (19)
C3—N1—C4	106.32 (17)	C18—C17—C22	117.0 (2)
C4—N1—C2	126.68 (18)	C22—C17—C1	122.07 (19)
C3—N2—C9	104.40 (19)	C17—C18—C19	122.1 (2)
C20—N3—C23	118.45 (17)	C17—C18—H18	119.0
C20—N3—C26	117.93 (16)	C19—C18—H18	119.0
C26—N3—C23	111.22 (17)	C18—C19—C20	121.2 (2)
O1—C1—C17	112.39 (17)	C18—C19—H19	119.4
O1—C1—C2	104.93 (17)	C20—C19—H19	119.4
O1—C1—H1	108.5	N3—C20—C21	121.36 (19)
C2—C1—H1	108.5	C19—C20—N3	122.12 (19)
C17—C1—C2	113.76 (17)	C19—C20—C21	116.4 (2)
C17—C1—H1	108.5	C20—C21—H21	119.2
N1—C2—C1	112.38 (17)	C22—C21—C20	121.6 (2)
N1—C2—H2A	109.1	C22—C21—H21	119.2
N1—C2—H2B	109.1	C17—C22—H22	119.2
C1—C2—H2A	109.1	C21—C22—C17	121.6 (2)
C1—C2—H2B	109.1	C21—C22—H22	119.2
H2A—C2—H2B	107.9	N3—C23—C24	110.09 (19)
N1—C3—H3	122.9	N3—C23—H23A	109.6
N2—C3—N1	114.2 (2)	N3—C23—H23B	109.6
N2—C3—H3	122.9	C24—C23—H23A	109.6
N1—C4—C5	132.8 (2)	C24—C23—H23B	109.6
N1—C4—C9	105.00 (19)	H23A—C23—H23B	108.2
C5—C4—C9	122.2 (2)	O2—C24—C23	112.08 (18)
C4—C5—H5	121.6	O2—C24—H24A	109.2
C6—C5—C4	116.9 (2)	O2—C24—H24B	109.2
C6—C5—H5	121.6	C23—C24—H24A	109.2
C5—C6—C7	121.4 (2)	C23—C24—H24B	109.2
C5—C6—H6	119.3	H24A—C24—H24B	107.9
C7—C6—H6	119.3	O2—C25—C26	112.0 (2)
C6—C7—H7	119.2	O2—C25—H25A	109.2
C8—C7—C6	121.7 (2)	O2—C25—H25B	109.2
C8—C7—H7	119.2	C26—C25—H25A	109.2
C7—C8—C9	117.8 (2)	C26—C25—H25B	109.2
C7—C8—H8	121.1	H25A—C25—H25B	107.9
C9—C8—H8	121.1	N3—C26—C25	110.64 (19)
N2—C9—C4	110.1 (2)	N3—C26—H26A	109.5
N2—C9—C8	129.9 (2)	N3—C26—H26B	109.5
C8—C9—C4	120.0 (2)	C25—C26—H26A	109.5
O1—C10—C11	108.21 (18)	C25—C26—H26B	109.5
O1—C10—H10A	110.1	H26A—C26—H26B	108.1
O1—C10—H10B	110.1	O3—C27—C28	111.1 (2)
C11—C10—H10A	110.1	O3—C27—C29	106.9 (2)
C11—C10—H10B	110.1	O3—C27—H27	108.8
H10A—C10—H10B	108.4	C28—C27—C29	112.4 (2)
C12—C11—C10	120.5 (2)	C28—C27—H27	108.8
C16—C11—C10	121.2 (2)	C29—C27—H27	108.8
C16—C11—C12	118.4 (2)	C27—C28—H28A	109.5
C11—C12—H12	119.7	C27—C28—H28B	109.5
C13—C12—C11	120.6 (2)	C27—C28—H28C	109.5
C13—C12—H12	119.7	H28A—C28—H28B	109.5
C12—C13—C14	119.4 (2)	H28A—C28—H28C	109.5
C12—C13—H13	120.3	H28B—C28—H28C	109.5
C14—C13—H13	120.3	C27—C29—H29A	109.5
C13—C14—Cl1	119.17 (19)	C27—C29—H29B	109.5
C15—C14—Cl1	119.5 (2)	C27—C29—H29C	109.5
C15—C14—C13	121.3 (2)	H29A—C29—H29B	109.5
C14—C15—H15	120.9	H29A—C29—H29C	109.5
C16—C15—C14	118.2 (2)	H29B—C29—H29C	109.5
C16—C15—H15	120.9
C10—O1—C1—C17	68.3 (2)	C8—C7—C6—C5	−0.5 (4)
C10—O1—C1—C2	−167.60 (17)	C9—C8—C7—C6	−0.5 (4)
C1—O1—C10—C11	175.73 (18)	N2—C9—C8—C7	−178.2 (2)
C25—O2—C24—C23	−60.4 (3)	C4—C9—C8—C7	0.8 (3)
C24—O2—C25—C26	59.3 (3)	C12—C11—C10—O1	−75.2 (3)
C3—N1—C2—C1	−70.9 (3)	C16—C11—C10—O1	104.8 (2)
C4—N1—C2—C1	108.7 (2)	C13—C12—C11—C16	1.7 (3)
C2—N1—C3—N2	179.53 (18)	C13—C12—C11—C10	−178.3 (2)
C4—N1—C3—N2	−0.2 (2)	C11—C12—C13—C14	0.5 (3)
C2—N1—C4—C5	1.5 (4)	Cl1—C14—C13—C12	175.85 (17)
C2—N1—C4—C9	−179.65 (18)	C15—C14—C13—C12	−1.8 (3)
C3—N1—C4—C5	−178.8 (2)	Cl1—C14—C15—C16	−176.86 (17)
C3—N1—C4—C9	0.0 (2)	C13—C14—C15—C16	0.8 (3)
C9—N2—C3—N1	0.2 (2)	C14—C15—C16—C11	1.5 (3)
C3—N2—C9—C4	−0.2 (2)	C15—C16—C11—C10	177.2 (2)
C3—N2—C9—C8	178.9 (2)	C15—C16—C11—C12	−2.8 (3)
C23—N3—C20—C19	−11.4 (3)	C18—C17—C1—O1	−115.5 (2)
C23—N3—C20—C21	172.8 (2)	C18—C17—C1—C2	125.5 (2)
C26—N3—C20—C19	−150.3 (2)	C22—C17—C1—O1	62.4 (3)
C26—N3—C20—C21	33.9 (3)	C22—C17—C1—C2	−56.7 (3)
C20—N3—C23—C24	165.53 (18)	C1—C17—C18—C19	178.1 (2)
C26—N3—C23—C24	−53.0 (2)	C22—C17—C18—C19	0.1 (3)
C20—N3—C26—C25	−166.0 (2)	C1—C17—C22—C21	−177.3 (2)
C23—N3—C26—C25	52.4 (3)	C18—C17—C22—C21	0.7 (3)
O1—C1—C2—N1	62.6 (2)	C20—C19—C18—C17	−0.7 (4)
C17—C1—C2—N1	−174.18 (18)	C18—C19—C20—N3	−175.6 (2)
N1—C4—C5—C6	177.8 (2)	C18—C19—C20—C21	0.3 (3)
C9—C4—C5—C6	−0.9 (3)	N3—C20—C21—C22	176.5 (2)
N1—C4—C9—N2	0.1 (2)	C17—C22—C21—C20	−1.0 (4)
N1—C4—C9—C8	−179.09 (19)	C19—C20—C21—C22	0.5 (3)
C5—C4—C9—N2	179.06 (18)	N3—C23—C24—O2	57.8 (3)
C5—C4—C9—C8	−0.1 (3)	N3—C26—C25—O2	−56.1 (3)
C4—C5—C6—C7	1.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N2i	0.85 (3)	2.08 (3)	2.916 (3)	170 (3)
C5—H5···O2ii	0.93	2.52	3.429 (3)	165
C2—H2B···Cg2i	0.97	2.68	3.465 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C4–C9 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N2i	0.85 (3)	2.08 (3)	2.916 (3)	170 (3)
C5—H5⋯O2ii	0.93	2.52	3.429 (3)	165
C2—H2B⋯Cg2i	0.97	2.68	3.465 (2)	138

Symmetry codes: (i) ; (ii) .