2-[2-(2-Anilino-4-oxo-3,4-dihydro-quinazolin-3-yl)phen-oxy]-3-phenyl-quinazolin-4(3H)-one methanol hemisolvate.

In the title compound, C(34)H(23)N(5)O(3)·0.5CH(3)OH, each pyrimid-in-one heterocycle and its adjacent benzene ring are almost coplanar, making dihedral angles of 0.69 (13) and 1.87 (13)°. The lower pyrimidinone ring makes a dihedral angle of 40.41 (15)° with the -NH- bonded phenyl ring. O-H⋯O hydrogen bonds and weak C-H⋯π inter-actions are observed in the crystal structure. The methanol solvent molecule is disordered over two positions of equal occupancy.

Related literature

For the biological activity of quinazoline-4(3H)-one derivatives, see: Pandeya et al.(1999 ▶); Shiba et al. (1997 ▶); Malamas & Millen (1991 ▶); Mannschreck et al. (1984 ▶); Kung et al. (1999 ▶); Bartroli et al. (1998 ▶); Palmer et al. (1997 ▶); Tsou et al. (2001 ▶); Matsuno et al.(2002 ▶). For the synthesis of the title compound, see: Yang et al. (2008 ▶).

Experimental

Crystal data

C34H23N5O3·0.5CH4O

M = 565.60

Monoclinic,

a = 24.268 (2) Å

b = 16.5049 (14) Å

c = 15.2929 (12) Å

β = 110.382 (1)°

V = 5741.9 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 292 K

0.32 × 0.25 × 0.24 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.963, T max = 0.979

16455 measured reflections

5631 independent reflections

3943 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.228

S = 1.04

5631 reflections

397 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.78 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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/S1600536810028011/bq2224sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028011/bq2224Isup2.hkl

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

C34H23N5O3·0.5CH4O	F(000) = 2360
Mr = 565.60	Dx = 1.309 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3884 reflections
a = 24.268 (2) Å	θ = 2.5–23.6°
b = 16.5049 (14) Å	µ = 0.09 mm−1
c = 15.2929 (12) Å	T = 292 K
β = 110.382 (1)°	Block, colorless
V = 5741.9 (8) Å3	0.32 × 0.25 × 0.24 mm
Z = 8

Bruker SMART APEX CCD area-detector diffractometer	5631 independent reflections
Radiation source: fine-focus sealed tube	3943 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −29→23
Tmin = 0.963, Tmax = 0.979	k = −20→20
16455 measured reflections	l = −18→18

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.228	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.1434P)2 + 2.1314P] where P = (Fo2 + 2Fc2)/3
5631 reflections	(Δ/σ)max = 0.002
397 parameters	Δρmax = 0.78 e Å−3
12 restraints	Δρmin = −0.26 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)
C1	0.33889 (11)	0.39224 (16)	0.95966 (18)	0.0574 (6)
H1	0.2986	0.3843	0.9429	0.069*
C2	0.37488 (14)	0.3822 (2)	1.0508 (2)	0.0749 (8)
H2	0.3587	0.3681	1.0956	0.090*
C3	0.43447 (15)	0.3929 (3)	1.0766 (2)	0.0890 (10)
H3	0.4586	0.3857	1.1384	0.107*
C4	0.45792 (13)	0.4139 (3)	1.0111 (2)	0.0921 (11)
H4	0.4983	0.4211	1.0284	0.110*
C5	0.42214 (12)	0.4248 (2)	0.9184 (2)	0.0709 (8)
H5	0.4385	0.4392	0.8739	0.085*
C6	0.36227 (10)	0.41392 (14)	0.89331 (17)	0.0478 (5)
C7	0.27029 (10)	0.43844 (13)	0.76026 (15)	0.0444 (5)
C8	0.18242 (10)	0.43060 (15)	0.62005 (16)	0.0491 (6)
C9	0.15259 (10)	0.46910 (14)	0.67699 (16)	0.0477 (5)
C10	0.09255 (11)	0.48514 (16)	0.6402 (2)	0.0600 (7)
H10	0.0712	0.4718	0.5786	0.072*
C11	0.06483 (12)	0.52059 (18)	0.6949 (2)	0.0688 (8)
H11	0.0247	0.5314	0.6704	0.083*
C12	0.09658 (13)	0.54019 (18)	0.7862 (2)	0.0689 (8)
H12	0.0775	0.5642	0.8229	0.083*
C13	0.15578 (12)	0.52491 (15)	0.8240 (2)	0.0587 (6)
H13	0.1766	0.5388	0.8857	0.070*
C14	0.18475 (10)	0.48859 (13)	0.76995 (16)	0.0458 (5)
C15	0.27546 (10)	0.37942 (14)	0.61502 (15)	0.0458 (5)
C16	0.29309 (12)	0.42318 (16)	0.55277 (17)	0.0565 (6)
H16	0.2841	0.4780	0.5433	0.068*
C17	0.32434 (13)	0.38468 (18)	0.50451 (19)	0.0642 (7)
H17	0.3371	0.4140	0.4632	0.077*
C18	0.33669 (12)	0.30324 (18)	0.51737 (18)	0.0614 (7)
H18	0.3570	0.2777	0.4836	0.074*
C19	0.31914 (11)	0.25893 (16)	0.58009 (17)	0.0535 (6)
H19	0.3279	0.2040	0.5893	0.064*
C20	0.28861 (10)	0.29777 (14)	0.62827 (15)	0.0457 (5)
C21	0.30048 (10)	0.22726 (13)	0.76894 (16)	0.0457 (5)
C22	0.38728 (11)	0.19895 (14)	0.88305 (17)	0.0527 (6)
C23	0.44826 (12)	0.20351 (18)	0.9158 (2)	0.0678 (7)
H23	0.4675	0.2278	0.8796	0.081*
C24	0.48029 (14)	0.1718 (2)	1.0022 (2)	0.0782 (9)
H24	0.5211	0.1757	1.0244	0.094*
C25	0.45238 (15)	0.1344 (2)	1.0559 (2)	0.0796 (9)
H25	0.4743	0.1129	1.1138	0.096*
C26	0.39234 (14)	0.12903 (18)	1.0239 (2)	0.0698 (8)
H26	0.3735	0.1033	1.0598	0.084*
C27	0.35942 (12)	0.16190 (15)	0.93765 (17)	0.0547 (6)
C28	0.29550 (12)	0.15817 (16)	0.90513 (18)	0.0570 (6)
C29	0.20409 (10)	0.20150 (14)	0.78235 (16)	0.0465 (5)
C30	0.17127 (12)	0.13978 (17)	0.72933 (18)	0.0598 (7)
H30	0.1896	0.0934	0.7182	0.072*
C31	0.11087 (13)	0.1470 (2)	0.6926 (2)	0.0734 (8)
H31	0.0884	0.1054	0.6564	0.088*
C32	0.08382 (12)	0.2155 (2)	0.7093 (2)	0.0707 (8)
H32	0.0431	0.2203	0.6843	0.085*
C33	0.11721 (13)	0.27667 (19)	0.7630 (2)	0.0713 (8)
H33	0.0990	0.3230	0.7744	0.086*
C34	0.17759 (12)	0.26988 (16)	0.8003 (2)	0.0615 (7)
H34	0.2001	0.3111	0.8372	0.074*
N1	0.32858 (9)	0.42035 (13)	0.79688 (14)	0.0520 (5)
N2	0.24407 (8)	0.47305 (12)	0.81070 (13)	0.0486 (5)
N3	0.24277 (8)	0.41832 (11)	0.66622 (13)	0.0461 (5)
N4	0.35614 (9)	0.23084 (12)	0.79476 (14)	0.0510 (5)
N5	0.26758 (9)	0.19548 (12)	0.81838 (13)	0.0494 (5)
O1	0.15912 (8)	0.40913 (13)	0.53964 (13)	0.0688 (5)
O2	0.26452 (7)	0.25565 (10)	0.68598 (11)	0.0513 (4)
O3	0.26588 (9)	0.12670 (15)	0.94629 (15)	0.0855 (7)
H20	0.3454	0.4038	0.7553	0.128*
C35	0.5532 (2)	0.4402 (4)	0.8065 (4)	0.0697 (15)	0.50
H35A	0.5858	0.4492	0.7857	0.105*	0.50
H35B	0.5644	0.4548	0.8711	0.105*	0.50
H35C	0.5205	0.4729	0.7703	0.105*	0.50
O5	0.53385 (15)	0.3409 (4)	0.7931 (3)	0.0959 (18)	0.50
H35	0.5000	0.3679	0.7500	0.144*

	U11	U22	U33	U12	U13	U23
C1	0.0490 (14)	0.0654 (16)	0.0556 (15)	0.0017 (12)	0.0153 (12)	0.0043 (12)
C2	0.0726 (19)	0.090 (2)	0.0585 (17)	0.0144 (16)	0.0187 (15)	0.0178 (15)
C3	0.071 (2)	0.119 (3)	0.0589 (18)	0.0104 (19)	0.0004 (16)	0.0188 (18)
C4	0.0460 (16)	0.128 (3)	0.081 (2)	−0.0047 (18)	−0.0044 (15)	0.015 (2)
C5	0.0473 (15)	0.094 (2)	0.0680 (17)	0.0001 (14)	0.0156 (13)	0.0115 (16)
C6	0.0442 (12)	0.0444 (12)	0.0483 (13)	0.0035 (10)	0.0080 (10)	−0.0035 (10)
C7	0.0442 (12)	0.0446 (12)	0.0427 (12)	−0.0025 (10)	0.0129 (10)	−0.0002 (9)
C8	0.0472 (13)	0.0523 (13)	0.0431 (13)	0.0004 (10)	0.0100 (10)	0.0033 (10)
C9	0.0455 (12)	0.0461 (12)	0.0508 (13)	−0.0005 (10)	0.0158 (10)	0.0040 (10)
C10	0.0455 (13)	0.0617 (15)	0.0686 (17)	−0.0002 (11)	0.0146 (12)	0.0048 (13)
C11	0.0464 (14)	0.0698 (18)	0.093 (2)	0.0073 (13)	0.0277 (15)	0.0050 (16)
C12	0.0618 (17)	0.0650 (17)	0.091 (2)	0.0062 (14)	0.0415 (17)	−0.0021 (15)
C13	0.0620 (16)	0.0545 (14)	0.0664 (16)	0.0029 (12)	0.0310 (13)	−0.0028 (12)
C14	0.0474 (12)	0.0390 (11)	0.0528 (13)	0.0007 (9)	0.0198 (11)	0.0029 (10)
C15	0.0465 (12)	0.0510 (13)	0.0396 (12)	0.0012 (10)	0.0145 (10)	−0.0007 (10)
C16	0.0686 (16)	0.0552 (14)	0.0501 (14)	0.0009 (12)	0.0263 (12)	0.0080 (11)
C17	0.0759 (18)	0.0719 (18)	0.0549 (15)	0.0002 (14)	0.0354 (14)	0.0089 (13)
C18	0.0617 (16)	0.0774 (18)	0.0519 (14)	0.0054 (13)	0.0284 (12)	−0.0057 (13)
C19	0.0525 (14)	0.0556 (14)	0.0519 (13)	0.0061 (11)	0.0174 (11)	−0.0013 (11)
C20	0.0439 (12)	0.0536 (13)	0.0389 (11)	−0.0010 (10)	0.0133 (10)	0.0047 (10)
C21	0.0489 (13)	0.0415 (11)	0.0468 (13)	0.0020 (10)	0.0170 (10)	0.0027 (10)
C22	0.0532 (14)	0.0446 (12)	0.0536 (14)	0.0046 (11)	0.0104 (11)	0.0031 (11)
C23	0.0557 (16)	0.0647 (16)	0.0731 (18)	−0.0019 (13)	0.0101 (14)	0.0070 (14)
C24	0.0592 (17)	0.077 (2)	0.078 (2)	0.0017 (15)	−0.0017 (15)	0.0021 (16)
C25	0.077 (2)	0.078 (2)	0.0643 (18)	0.0122 (16)	−0.0001 (16)	0.0130 (16)
C26	0.078 (2)	0.0664 (17)	0.0570 (16)	0.0106 (15)	0.0134 (14)	0.0137 (14)
C27	0.0611 (15)	0.0498 (13)	0.0492 (14)	0.0069 (11)	0.0143 (12)	0.0060 (11)
C28	0.0609 (15)	0.0572 (15)	0.0525 (14)	0.0055 (12)	0.0191 (12)	0.0130 (12)
C29	0.0480 (13)	0.0471 (12)	0.0458 (12)	−0.0003 (10)	0.0181 (10)	0.0076 (10)
C30	0.0643 (16)	0.0556 (14)	0.0570 (15)	0.0019 (12)	0.0182 (13)	−0.0006 (12)
C31	0.0647 (18)	0.079 (2)	0.0650 (18)	−0.0138 (15)	0.0076 (14)	−0.0048 (15)
C32	0.0490 (15)	0.088 (2)	0.0686 (18)	0.0013 (14)	0.0126 (13)	0.0145 (16)
C33	0.0608 (17)	0.0680 (17)	0.088 (2)	0.0112 (14)	0.0292 (16)	0.0046 (16)
C34	0.0552 (15)	0.0544 (15)	0.0740 (17)	−0.0031 (12)	0.0214 (13)	−0.0056 (13)
N1	0.0453 (11)	0.0629 (12)	0.0463 (11)	0.0034 (9)	0.0140 (9)	−0.0051 (9)
N2	0.0471 (11)	0.0502 (11)	0.0477 (11)	0.0012 (8)	0.0155 (9)	−0.0053 (9)
N3	0.0470 (11)	0.0496 (11)	0.0419 (10)	0.0021 (8)	0.0158 (8)	−0.0001 (8)
N4	0.0492 (11)	0.0518 (11)	0.0505 (11)	0.0022 (9)	0.0153 (9)	0.0058 (9)
N5	0.0513 (11)	0.0480 (10)	0.0500 (11)	0.0031 (9)	0.0190 (9)	0.0110 (9)
O1	0.0585 (11)	0.0912 (14)	0.0487 (11)	0.0062 (10)	0.0088 (9)	−0.0088 (10)
O2	0.0474 (9)	0.0591 (10)	0.0468 (9)	0.0021 (7)	0.0156 (7)	0.0142 (7)
O3	0.0739 (14)	0.1109 (17)	0.0767 (14)	0.0072 (12)	0.0324 (11)	0.0445 (13)
C35	0.053 (3)	0.090 (4)	0.062 (3)	−0.010 (3)	0.014 (3)	−0.016 (3)
O5	0.0276 (17)	0.201 (6)	0.058 (2)	−0.005 (2)	0.0139 (16)	0.020 (3)

C1—C6	1.371 (4)	C19—H19	0.9300
C1—C2	1.373 (4)	C20—O2	1.401 (3)
C1—H1	0.9300	C21—N4	1.270 (3)
C2—C3	1.372 (4)	C21—O2	1.349 (3)
C2—H2	0.9300	C21—N5	1.380 (3)
C3—C4	1.357 (5)	C22—C27	1.386 (4)
C3—H3	0.9300	C22—C23	1.389 (4)
C4—C5	1.393 (4)	C22—N4	1.400 (3)
C4—H4	0.9300	C23—C24	1.382 (4)
C5—C6	1.379 (3)	C23—H23	0.9300
C5—H5	0.9300	C24—C25	1.378 (5)
C6—N1	1.419 (3)	C24—H24	0.9300
C7—N2	1.292 (3)	C25—C26	1.369 (4)
C7—N1	1.361 (3)	C25—H25	0.9300
C7—N3	1.398 (3)	C26—C27	1.392 (4)
C8—O1	1.214 (3)	C26—H26	0.9300
C8—N3	1.402 (3)	C27—C28	1.456 (4)
C8—C9	1.458 (3)	C28—O3	1.224 (3)
C9—C10	1.392 (3)	C28—N5	1.404 (3)
C9—C14	1.400 (3)	C29—C30	1.371 (4)
C10—C11	1.373 (4)	C29—C34	1.374 (3)
C10—H10	0.9300	C29—N5	1.448 (3)
C11—C12	1.378 (4)	C30—C31	1.380 (4)
C11—H11	0.9300	C30—H30	0.9300
C12—C13	1.373 (4)	C31—C32	1.375 (4)
C12—H12	0.9300	C31—H31	0.9300
C13—C14	1.394 (3)	C32—C33	1.375 (4)
C13—H13	0.9300	C32—H32	0.9300
C14—N2	1.379 (3)	C33—C34	1.379 (4)
C15—C16	1.376 (3)	C33—H33	0.9300
C15—C20	1.383 (3)	C34—H34	0.9300
C15—N3	1.445 (3)	N1—H20	0.9098
C16—C17	1.383 (4)	C35—O5	1.698 (9)
C16—H16	0.9300	C35—H35A	0.9600
C17—C18	1.376 (4)	C35—H35B	0.9600
C17—H17	0.9300	C35—H35C	0.9600
C18—C19	1.386 (4)	O5—O5i	1.711 (7)
C18—H18	0.9300	O5—H35	0.9646
C19—C20	1.372 (3)
C6—C1—C2	120.1 (3)	N4—C21—N5	127.1 (2)
C6—C1—H1	119.9	O2—C21—N5	109.81 (19)
C2—C1—H1	119.9	C27—C22—C23	119.2 (2)
C3—C2—C1	120.6 (3)	C27—C22—N4	122.3 (2)
C3—C2—H2	119.7	C23—C22—N4	118.5 (2)
C1—C2—H2	119.7	C24—C23—C22	119.9 (3)
C4—C3—C2	119.5 (3)	C24—C23—H23	120.1
C4—C3—H3	120.2	C22—C23—H23	120.1
C2—C3—H3	120.2	C25—C24—C23	120.6 (3)
C3—C4—C5	120.7 (3)	C25—C24—H24	119.7
C3—C4—H4	119.6	C23—C24—H24	119.7
C5—C4—H4	119.6	C26—C25—C24	119.9 (3)
C6—C5—C4	119.3 (3)	C26—C25—H25	120.1
C6—C5—H5	120.3	C24—C25—H25	120.1
C4—C5—H5	120.3	C25—C26—C27	120.1 (3)
C1—C6—C5	119.7 (2)	C25—C26—H26	119.9
C1—C6—N1	123.4 (2)	C27—C26—H26	119.9
C5—C6—N1	116.7 (2)	C22—C27—C26	120.2 (3)
N2—C7—N1	120.6 (2)	C22—C27—C28	119.9 (2)
N2—C7—N3	124.1 (2)	C26—C27—C28	119.9 (3)
N1—C7—N3	115.27 (19)	O3—C28—N5	119.7 (2)
O1—C8—N3	120.3 (2)	O3—C28—C27	126.1 (2)
O1—C8—C9	125.4 (2)	N5—C28—C27	114.2 (2)
N3—C8—C9	114.3 (2)	C30—C29—C34	120.8 (2)
C10—C9—C14	120.1 (2)	C30—C29—N5	119.8 (2)
C10—C9—C8	120.6 (2)	C34—C29—N5	119.4 (2)
C14—C9—C8	119.3 (2)	C29—C30—C31	119.5 (3)
C11—C10—C9	120.1 (3)	C29—C30—H30	120.2
C11—C10—H10	120.0	C31—C30—H30	120.2
C9—C10—H10	120.0	C32—C31—C30	120.2 (3)
C10—C11—C12	119.8 (2)	C32—C31—H31	119.9
C10—C11—H11	120.1	C30—C31—H31	119.9
C12—C11—H11	120.1	C31—C32—C33	119.7 (3)
C13—C12—C11	121.2 (3)	C31—C32—H32	120.2
C13—C12—H12	119.4	C33—C32—H32	120.2
C11—C12—H12	119.4	C32—C33—C34	120.5 (3)
C12—C13—C14	120.0 (3)	C32—C33—H33	119.7
C12—C13—H13	120.0	C34—C33—H33	119.7
C14—C13—H13	120.0	C29—C34—C33	119.2 (3)
N2—C14—C13	118.3 (2)	C29—C34—H34	120.4
N2—C14—C9	122.8 (2)	C33—C34—H34	120.4
C13—C14—C9	118.9 (2)	C7—N1—C6	125.7 (2)
C16—C15—C20	120.1 (2)	C7—N1—H20	115.7
C16—C15—N3	120.2 (2)	C6—N1—H20	117.9
C20—C15—N3	119.72 (19)	C7—N2—C14	117.8 (2)
C15—C16—C17	119.2 (2)	C7—N3—C8	121.65 (19)
C15—C16—H16	120.4	C7—N3—C15	120.48 (19)
C17—C16—H16	120.4	C8—N3—C15	117.77 (18)
C18—C17—C16	120.3 (2)	C21—N4—C22	116.2 (2)
C18—C17—H17	119.8	C21—N5—C28	120.2 (2)
C16—C17—H17	119.8	C21—N5—C29	120.49 (18)
C17—C18—C19	120.7 (2)	C28—N5—C29	119.28 (19)
C17—C18—H18	119.7	C21—O2—C20	119.30 (17)
C19—C18—H18	119.7	O5—C35—H35A	109.5
C20—C19—C18	118.6 (2)	O5—C35—H35B	109.5
C20—C19—H19	120.7	H35A—C35—H35B	109.5
C18—C19—H19	120.7	O5—C35—H35C	109.5
C19—C20—C15	121.1 (2)	H35A—C35—H35C	109.5
C19—C20—O2	121.9 (2)	H35B—C35—H35C	109.5
C15—C20—O2	116.73 (19)	C35—O5—O5i	104.1 (2)
N4—C21—O2	123.1 (2)
C6—C1—C2—C3	−0.7 (5)	C34—C29—C30—C31	0.9 (4)
C1—C2—C3—C4	0.3 (6)	N5—C29—C30—C31	−177.9 (2)
C2—C3—C4—C5	0.1 (6)	C29—C30—C31—C32	−0.2 (4)
C3—C4—C5—C6	−0.1 (6)	C30—C31—C32—C33	−0.2 (5)
C2—C1—C6—C5	0.7 (4)	C31—C32—C33—C34	0.0 (5)
C2—C1—C6—N1	175.8 (3)	C30—C29—C34—C33	−1.1 (4)
C4—C5—C6—C1	−0.3 (4)	N5—C29—C34—C33	177.7 (2)
C4—C5—C6—N1	−175.8 (3)	C32—C33—C34—C29	0.6 (4)
O1—C8—C9—C10	−0.7 (4)	N2—C7—N1—C6	19.3 (4)
N3—C8—C9—C10	179.9 (2)	N3—C7—N1—C6	−161.8 (2)
O1—C8—C9—C14	178.1 (2)	C1—C6—N1—C7	27.8 (4)
N3—C8—C9—C14	−1.2 (3)	C5—C6—N1—C7	−156.9 (2)
C14—C9—C10—C11	0.4 (4)	N1—C7—N2—C14	−179.0 (2)
C8—C9—C10—C11	179.3 (2)	N3—C7—N2—C14	2.3 (3)
C9—C10—C11—C12	0.0 (4)	C13—C14—N2—C7	179.1 (2)
C10—C11—C12—C13	0.0 (5)	C9—C14—N2—C7	−0.6 (3)
C11—C12—C13—C14	−0.3 (4)	N2—C7—N3—C8	−3.6 (3)
C12—C13—C14—N2	−179.0 (2)	N1—C7—N3—C8	177.6 (2)
C12—C13—C14—C9	0.7 (4)	N2—C7—N3—C15	−179.8 (2)
C10—C9—C14—N2	179.0 (2)	N1—C7—N3—C15	1.3 (3)
C8—C9—C14—N2	0.1 (3)	O1—C8—N3—C7	−176.6 (2)
C10—C9—C14—C13	−0.7 (3)	C9—C8—N3—C7	2.8 (3)
C8—C9—C14—C13	−179.6 (2)	O1—C8—N3—C15	−0.2 (3)
C20—C15—C16—C17	−0.5 (4)	C9—C8—N3—C15	179.16 (19)
N3—C15—C16—C17	−180.0 (2)	C16—C15—N3—C7	−103.9 (3)
C15—C16—C17—C18	1.2 (4)	C20—C15—N3—C7	76.6 (3)
C16—C17—C18—C19	−1.3 (4)	C16—C15—N3—C8	79.7 (3)
C17—C18—C19—C20	0.7 (4)	C20—C15—N3—C8	−99.8 (3)
C18—C19—C20—C15	0.0 (4)	O2—C21—N4—C22	179.8 (2)
C18—C19—C20—O2	173.7 (2)	N5—C21—N4—C22	0.0 (4)
C16—C15—C20—C19	−0.1 (4)	C27—C22—N4—C21	3.1 (3)
N3—C15—C20—C19	179.4 (2)	C23—C22—N4—C21	−178.1 (2)
C16—C15—C20—O2	−174.2 (2)	N4—C21—N5—C28	−3.7 (4)
N3—C15—C20—O2	5.3 (3)	O2—C21—N5—C28	176.5 (2)
C27—C22—C23—C24	−0.5 (4)	N4—C21—N5—C29	175.2 (2)
N4—C22—C23—C24	−179.3 (3)	O2—C21—N5—C29	−4.6 (3)
C22—C23—C24—C25	1.0 (5)	O3—C28—N5—C21	−176.4 (2)
C23—C24—C25—C26	−0.5 (5)	C27—C28—N5—C21	3.9 (3)
C24—C25—C26—C27	−0.6 (5)	O3—C28—N5—C29	4.7 (4)
C23—C22—C27—C26	−0.6 (4)	C27—C28—N5—C29	−175.0 (2)
N4—C22—C27—C26	178.2 (2)	C30—C29—N5—C21	92.6 (3)
C23—C22—C27—C28	178.7 (2)	C34—C29—N5—C21	−86.1 (3)
N4—C22—C27—C28	−2.5 (4)	C30—C29—N5—C28	−88.5 (3)
C25—C26—C27—C22	1.2 (4)	C34—C29—N5—C28	92.8 (3)
C25—C26—C27—C28	−178.1 (3)	N4—C21—O2—C20	−6.0 (3)
C22—C27—C28—O3	179.3 (3)	N5—C21—O2—C20	173.79 (18)
C26—C27—C28—O3	−1.3 (4)	C19—C20—O2—C21	73.6 (3)
C22—C27—C28—N5	−1.0 (3)	C15—C20—O2—C21	−112.4 (2)
C26—C27—C28—N5	178.3 (2)

Cg1 is the centroid of the C29–C34 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O5—H35···O5i	0.96	0.96	1.711 (7)	125
C2—H2···Cg1ii	0.93	2.75	3.617 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C29–C34 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H35⋯O5i	0.96	0.96	1.711 (7)	125
C2—H2⋯Cg1ii	0.93	2.75	3.617 (3)	155

Symmetry codes: (i) ; (ii) .