3,3'-Bis(4-chloro-phen-yl)-2,2'-(m-phenyl-enedi-oxy)diquinazolin-4(3H)-one.

In the title compound, C(34)H(20)Cl(2)N(4)O(4), the two quinazoline heterocyclic systems and the adjacent chloro-benzene rings are not coplanar, but oriented at dihedral angles of 66.66 (13) and 52.48 (12)°, respectively. The quinazoline ring systems are nearly planar, with dihedral angles between the planes of the two rings of 5.43 (16) and 3.40 (14)°, and are oriented at dihedral angles of 79.73 (13) and 83.52 (13)° with respect to the adjacent benzene ring between them. Inter-molecular C-H⋯O hydrogen bonds contribute to the stability of the structure. In addition, weak π-π stacking inter-actions [centroid-to-centroid distances = 3.872 (1) and 3.876 (1) Å] are observed in the crystal structure.

Related literature

Many derivatives of quinazoline-4(3H)-one have been prepared, and their biological properties, such as anti­microbial, anti­diabetic, anti­convulsant, anti­bacterial and anti­fungal activities, and their action as protein tyrosine kinase inhibitors, EGFR inhibitors and PDGFR phospho­rylation inhibitors, have been studied by: 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, see: Yang et al. (2008 ▶). For related structures, see: Hu et al. (2006 ▶); Qu et al. (2008 ▶); Zeng et al. (2008 ▶); Sun et al. (2008 ▶).

Experimental

Crystal data

C34H20Cl2N4O4

M = 619.44

Monoclinic,

a = 28.043 (2) Å

b = 11.3563 (8) Å

c = 21.5497 (16) Å

β = 122.7440 (10)°

V = 5772.2 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.27 mm−1

T = 296 (2) K

0.23 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: none

22711 measured reflections

6251 independent reflections

3432 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.160

S = 1.01

6251 reflections

397 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.28 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/S1600536808040567/at2685sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040567/at2685Isup2.hkl

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

C34H20Cl2N4O4	F(000) = 2544
Mr = 619.44	Dx = 1.426 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1972 reflections
a = 28.043 (2) Å	θ = 2.3–19.8°
b = 11.3563 (8) Å	µ = 0.27 mm−1
c = 21.5497 (16) Å	T = 296 K
β = 122.744 (1)°	Block, colourless
V = 5772.2 (7) Å3	0.23 × 0.10 × 0.10 mm
Z = 8

Bruker SMART APEX CCD area-detector diffractometer	3432 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.069
graphite	θmax = 27.0°, θmin = 1.7°
φ and ω scans	h = −35→35
22711 measured reflections	k = −14→14
6251 independent reflections	l = −26→27

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0656P)2] where P = (Fo2 + 2Fc2)/3
6251 reflections	(Δ/σ)max < 0.001
397 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.28 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
C1	0.15141 (12)	0.7594 (3)	0.30121 (18)	0.0559 (9)
C2	0.16014 (13)	0.6517 (3)	0.28105 (19)	0.0618 (9)
H2	0.1349	0.5902	0.2705	0.074*
C3	0.20679 (12)	0.6352 (3)	0.27648 (17)	0.0562 (9)
H3	0.2130	0.5624	0.2623	0.067*
C4	0.24445 (11)	0.7262 (3)	0.29288 (15)	0.0425 (7)
C5	0.23582 (12)	0.8331 (3)	0.31471 (17)	0.0545 (8)
H5	0.2617	0.8938	0.3269	0.065*
C6	0.18899 (12)	0.8510 (3)	0.31871 (19)	0.0615 (9)
H6	0.1828	0.9237	0.3330	0.074*
C7	0.29051 (12)	0.7746 (3)	0.22679 (17)	0.0502 (8)
C8	0.33543 (12)	0.7466 (3)	0.21498 (16)	0.0485 (8)
C9	0.33834 (15)	0.8010 (3)	0.15926 (19)	0.0705 (10)
H9	0.3132	0.8613	0.1318	0.085*
C10	0.37794 (16)	0.7665 (4)	0.1447 (2)	0.0827 (12)
H10	0.3796	0.8031	0.1073	0.099*
C11	0.41546 (16)	0.6774 (4)	0.1854 (2)	0.0776 (12)
H11	0.4419	0.6536	0.1746	0.093*
C12	0.41441 (13)	0.6231 (3)	0.24197 (17)	0.0597 (9)
H12	0.4401	0.5634	0.2691	0.072*
C13	0.37438 (11)	0.6583 (3)	0.25844 (16)	0.0460 (7)
C14	0.33712 (11)	0.6382 (2)	0.32842 (15)	0.0384 (7)
C15	0.38186 (11)	0.5356 (2)	0.44066 (15)	0.0359 (7)
C16	0.43022 (11)	0.5918 (2)	0.49417 (16)	0.0434 (7)
H16	0.4341	0.6728	0.4923	0.052*
C17	0.47308 (12)	0.5260 (3)	0.55090 (16)	0.0510 (8)
H17	0.5061	0.5629	0.5876	0.061*
C18	0.46706 (11)	0.4053 (3)	0.55324 (15)	0.0430 (7)
H18	0.4958	0.3604	0.5912	0.052*
C19	0.41816 (11)	0.3536 (2)	0.49879 (15)	0.0346 (6)
C20	0.37475 (10)	0.4164 (2)	0.44153 (15)	0.0362 (6)
H20	0.3418	0.3794	0.4048	0.043*
C21	0.42029 (10)	0.1591 (2)	0.46272 (15)	0.0365 (6)
C22	0.46375 (11)	0.1061 (2)	0.40343 (15)	0.0402 (7)
C23	0.49672 (11)	0.1357 (3)	0.37574 (16)	0.0507 (8)
H23	0.5096	0.2126	0.3803	0.061*
C24	0.51062 (12)	0.0527 (3)	0.34157 (18)	0.0626 (9)
H24	0.5332	0.0736	0.3238	0.075*
C25	0.49123 (13)	−0.0619 (3)	0.33343 (18)	0.0616 (9)
H25	0.5011	−0.1179	0.3108	0.074*
C26	0.45743 (11)	−0.0925 (3)	0.35886 (17)	0.0532 (8)
H26	0.4441	−0.1692	0.3531	0.064*
C27	0.44305 (10)	−0.0085 (2)	0.39337 (15)	0.0388 (7)
C28	0.40453 (11)	−0.0402 (3)	0.41594 (16)	0.0432 (7)
C29	0.35068 (11)	0.0301 (2)	0.46823 (15)	0.0404 (7)
C30	0.30465 (12)	0.1049 (3)	0.44078 (17)	0.0490 (8)
H30	0.3016	0.1704	0.4129	0.059*
C31	0.26329 (13)	0.0809 (3)	0.45527 (19)	0.0628 (9)
H31	0.2325	0.1315	0.4379	0.075*
C32	0.26727 (14)	−0.0164 (3)	0.4949 (2)	0.0614 (9)
C33	0.31256 (14)	−0.0906 (3)	0.52176 (18)	0.0628 (9)
H33	0.3150	−0.1568	0.5487	0.075*
C34	0.35451 (12)	−0.0670 (3)	0.50883 (16)	0.0516 (8)
H34	0.3856	−0.1170	0.5276	0.062*
Cl1	0.09206 (4)	0.78360 (10)	0.30638 (6)	0.0883 (4)
Cl2	0.21428 (5)	−0.04566 (12)	0.51094 (7)	0.1140 (5)
N1	0.29124 (9)	0.7099 (2)	0.28274 (13)	0.0414 (6)
N2	0.37633 (9)	0.6075 (2)	0.31840 (12)	0.0417 (6)
N3	0.45216 (9)	0.19030 (19)	0.44073 (12)	0.0405 (6)
N4	0.39348 (9)	0.05110 (19)	0.45116 (12)	0.0384 (6)
O1	0.33518 (7)	0.60201 (16)	0.38599 (10)	0.0447 (5)
O2	0.25236 (9)	0.8446 (2)	0.18965 (12)	0.0715 (7)
O3	0.40913 (7)	0.23167 (15)	0.50289 (10)	0.0408 (5)
O4	0.38040 (9)	−0.13455 (18)	0.40336 (13)	0.0649 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0412 (16)	0.061 (2)	0.063 (2)	0.0031 (16)	0.0265 (16)	0.0035 (18)
C2	0.0488 (18)	0.049 (2)	0.082 (3)	−0.0122 (16)	0.0319 (18)	−0.0058 (19)
C3	0.0533 (18)	0.0416 (19)	0.068 (2)	−0.0043 (16)	0.0293 (17)	−0.0063 (17)
C4	0.0335 (14)	0.0388 (18)	0.0436 (18)	0.0036 (13)	0.0132 (13)	0.0048 (14)
C5	0.0429 (17)	0.043 (2)	0.069 (2)	−0.0033 (15)	0.0247 (16)	−0.0038 (17)
C6	0.0452 (17)	0.047 (2)	0.082 (3)	0.0029 (16)	0.0282 (17)	−0.0100 (18)
C7	0.0454 (17)	0.048 (2)	0.0401 (19)	−0.0037 (15)	0.0117 (15)	0.0051 (16)
C8	0.0494 (17)	0.051 (2)	0.0359 (18)	−0.0070 (15)	0.0172 (15)	0.0045 (15)
C9	0.069 (2)	0.081 (3)	0.052 (2)	−0.010 (2)	0.0263 (19)	0.013 (2)
C10	0.072 (2)	0.123 (4)	0.054 (2)	−0.017 (3)	0.035 (2)	0.006 (3)
C11	0.075 (2)	0.110 (4)	0.062 (3)	−0.016 (2)	0.046 (2)	−0.013 (2)
C12	0.0563 (19)	0.074 (3)	0.051 (2)	−0.0059 (17)	0.0307 (17)	−0.0092 (18)
C13	0.0439 (16)	0.050 (2)	0.0389 (18)	−0.0101 (14)	0.0189 (14)	−0.0082 (15)
C14	0.0393 (15)	0.0325 (17)	0.0362 (17)	−0.0018 (13)	0.0158 (13)	0.0015 (13)
C15	0.0382 (14)	0.0334 (17)	0.0399 (17)	0.0063 (13)	0.0235 (13)	0.0072 (14)
C16	0.0502 (17)	0.0269 (16)	0.0521 (19)	−0.0039 (13)	0.0270 (15)	−0.0011 (14)
C17	0.0451 (17)	0.043 (2)	0.047 (2)	−0.0094 (14)	0.0135 (15)	−0.0039 (16)
C18	0.0419 (16)	0.0392 (18)	0.0384 (17)	0.0024 (13)	0.0156 (14)	0.0055 (14)
C19	0.0432 (15)	0.0255 (15)	0.0422 (17)	−0.0030 (12)	0.0278 (14)	−0.0001 (13)
C20	0.0329 (14)	0.0360 (17)	0.0365 (16)	−0.0042 (12)	0.0167 (12)	−0.0052 (13)
C21	0.0370 (14)	0.0288 (16)	0.0414 (17)	0.0008 (12)	0.0197 (13)	−0.0009 (13)
C22	0.0365 (14)	0.0397 (18)	0.0420 (17)	−0.0023 (13)	0.0197 (13)	−0.0031 (14)
C23	0.0518 (17)	0.052 (2)	0.054 (2)	−0.0095 (15)	0.0329 (16)	−0.0074 (16)
C24	0.0541 (19)	0.082 (3)	0.063 (2)	−0.0146 (19)	0.0385 (18)	−0.018 (2)
C25	0.0528 (18)	0.069 (2)	0.067 (2)	0.0015 (18)	0.0351 (18)	−0.018 (2)
C26	0.0444 (16)	0.048 (2)	0.064 (2)	−0.0031 (15)	0.0278 (16)	−0.0148 (17)
C27	0.0325 (14)	0.0362 (17)	0.0429 (17)	−0.0004 (12)	0.0171 (13)	−0.0052 (14)
C28	0.0417 (15)	0.0326 (17)	0.0532 (19)	0.0014 (14)	0.0243 (14)	−0.0015 (15)
C29	0.0385 (15)	0.0370 (17)	0.0476 (18)	−0.0055 (13)	0.0247 (14)	−0.0008 (15)
C30	0.0478 (16)	0.0437 (19)	0.060 (2)	0.0019 (15)	0.0320 (16)	0.0043 (16)
C31	0.0513 (19)	0.066 (2)	0.079 (3)	0.0040 (17)	0.0404 (19)	−0.005 (2)
C32	0.065 (2)	0.070 (3)	0.071 (2)	−0.0168 (19)	0.051 (2)	−0.011 (2)
C33	0.073 (2)	0.066 (2)	0.058 (2)	−0.013 (2)	0.0403 (19)	0.0077 (19)
C34	0.0539 (18)	0.046 (2)	0.052 (2)	0.0009 (15)	0.0267 (16)	0.0093 (16)
Cl1	0.0611 (5)	0.0904 (8)	0.1270 (9)	0.0016 (5)	0.0599 (6)	−0.0005 (7)
Cl2	0.1066 (8)	0.1518 (12)	0.1397 (11)	−0.0316 (8)	0.1032 (8)	−0.0167 (9)
N1	0.0382 (12)	0.0372 (14)	0.0401 (14)	0.0015 (11)	0.0156 (11)	0.0056 (12)
N2	0.0447 (13)	0.0413 (15)	0.0408 (14)	0.0015 (11)	0.0243 (12)	0.0008 (12)
N3	0.0452 (13)	0.0337 (14)	0.0461 (15)	−0.0044 (11)	0.0271 (12)	−0.0036 (12)
N4	0.0415 (12)	0.0280 (13)	0.0506 (15)	−0.0043 (10)	0.0280 (12)	−0.0044 (11)
O1	0.0427 (10)	0.0424 (12)	0.0497 (12)	0.0110 (9)	0.0255 (10)	0.0148 (10)
O2	0.0596 (13)	0.0775 (17)	0.0605 (15)	0.0203 (13)	0.0214 (12)	0.0328 (14)
O3	0.0572 (11)	0.0245 (10)	0.0509 (13)	−0.0027 (9)	0.0358 (10)	−0.0013 (9)
O4	0.0691 (14)	0.0408 (13)	0.1020 (19)	−0.0178 (11)	0.0576 (14)	−0.0200 (13)

C1—C2	1.364 (4)	C17—H17	0.9300
C1—C6	1.380 (4)	C18—C19	1.365 (4)
C1—Cl1	1.749 (3)	C18—H18	0.9300
C2—C3	1.377 (4)	C19—C20	1.374 (3)
C2—H2	0.9300	C19—O3	1.419 (3)
C3—C4	1.380 (4)	C20—H20	0.9300
C3—H3	0.9300	C21—N3	1.268 (3)
C4—C5	1.370 (4)	C21—O3	1.349 (3)
C4—N1	1.454 (3)	C21—N4	1.389 (3)
C5—C6	1.377 (4)	C22—C23	1.386 (4)
C5—H5	0.9300	C22—C27	1.394 (4)
C6—H6	0.9300	C22—N3	1.396 (3)
C7—O2	1.221 (3)	C23—C24	1.376 (4)
C7—N1	1.402 (4)	C23—H23	0.9300
C7—C8	1.449 (4)	C24—C25	1.384 (4)
C8—C9	1.392 (4)	C24—H24	0.9300
C8—C13	1.403 (4)	C25—C26	1.372 (4)
C9—C10	1.364 (5)	C25—H25	0.9300
C9—H9	0.9300	C26—C27	1.396 (4)
C10—C11	1.379 (5)	C26—H26	0.9300
C10—H10	0.9300	C27—C28	1.450 (4)
C11—C12	1.380 (5)	C28—O4	1.217 (3)
C11—H11	0.9300	C28—N4	1.415 (3)
C12—C13	1.406 (4)	C29—C34	1.376 (4)
C12—H12	0.9300	C29—C30	1.382 (4)
C13—N2	1.389 (3)	C29—N4	1.453 (3)
C14—N2	1.278 (3)	C30—C31	1.381 (4)
C14—O1	1.336 (3)	C30—H30	0.9300
C14—N1	1.385 (3)	C31—C32	1.364 (5)
C15—C20	1.370 (4)	C31—H31	0.9300
C15—C16	1.372 (4)	C32—C33	1.364 (5)
C15—O1	1.415 (3)	C32—Cl2	1.730 (3)
C16—C17	1.381 (4)	C33—C34	1.374 (4)
C16—H16	0.9300	C33—H33	0.9300
C17—C18	1.385 (4)	C34—H34	0.9300
C2—C1—C6	121.4 (3)	C20—C19—O3	117.5 (2)
C2—C1—Cl1	120.1 (3)	C15—C20—C19	117.4 (2)
C6—C1—Cl1	118.5 (3)	C15—C20—H20	121.3
C1—C2—C3	119.0 (3)	C19—C20—H20	121.3
C1—C2—H2	120.5	N3—C21—O3	121.6 (2)
C3—C2—H2	120.5	N3—C21—N4	127.1 (2)
C2—C3—C4	120.4 (3)	O3—C21—N4	111.3 (2)
C2—C3—H3	119.8	C23—C22—C27	118.6 (3)
C4—C3—H3	119.8	C23—C22—N3	119.9 (3)
C5—C4—C3	119.9 (3)	C27—C22—N3	121.5 (2)
C5—C4—N1	120.4 (3)	C24—C23—C22	120.8 (3)
C3—C4—N1	119.6 (3)	C24—C23—H23	119.6
C4—C5—C6	120.3 (3)	C22—C23—H23	119.6
C4—C5—H5	119.9	C23—C24—C25	120.4 (3)
C6—C5—H5	119.9	C23—C24—H24	119.8
C5—C6—C1	119.0 (3)	C25—C24—H24	119.8
C5—C6—H6	120.5	C26—C25—C24	119.8 (3)
C1—C6—H6	120.5	C26—C25—H25	120.1
O2—C7—N1	120.3 (3)	C24—C25—H25	120.1
O2—C7—C8	124.4 (3)	C25—C26—C27	120.0 (3)
N1—C7—C8	115.2 (3)	C25—C26—H26	120.0
C9—C8—C13	120.4 (3)	C27—C26—H26	120.0
C9—C8—C7	121.1 (3)	C22—C27—C26	120.3 (3)
C13—C8—C7	118.5 (3)	C22—C27—C28	120.2 (2)
C10—C9—C8	120.3 (4)	C26—C27—C28	119.4 (3)
C10—C9—H9	119.8	O4—C28—N4	120.5 (3)
C8—C9—H9	119.8	O4—C28—C27	124.7 (3)
C9—C10—C11	120.0 (4)	N4—C28—C27	114.6 (2)
C9—C10—H10	120.0	C34—C29—C30	119.9 (3)
C11—C10—H10	120.0	C34—C29—N4	120.1 (2)
C10—C11—C12	121.1 (3)	C30—C29—N4	119.9 (2)
C10—C11—H11	119.5	C31—C30—C29	119.1 (3)
C12—C11—H11	119.5	C31—C30—H30	120.5
C11—C12—C13	119.8 (3)	C29—C30—H30	120.5
C11—C12—H12	120.1	C32—C31—C30	120.5 (3)
C13—C12—H12	120.1	C32—C31—H31	119.8
N2—C13—C8	122.8 (3)	C30—C31—H31	119.8
N2—C13—C12	118.8 (3)	C31—C32—C33	120.5 (3)
C8—C13—C12	118.3 (3)	C31—C32—Cl2	119.5 (3)
N2—C14—O1	123.0 (2)	C33—C32—Cl2	120.0 (3)
N2—C14—N1	126.4 (3)	C32—C33—C34	119.8 (3)
O1—C14—N1	110.6 (2)	C32—C33—H33	120.1
C20—C15—C16	122.2 (3)	C34—C33—H33	120.1
C20—C15—O1	117.5 (2)	C33—C34—C29	120.3 (3)
C16—C15—O1	120.1 (2)	C33—C34—H34	119.9
C15—C16—C17	118.9 (3)	C29—C34—H34	119.9
C15—C16—H16	120.5	C14—N1—C7	119.7 (2)
C17—C16—H16	120.5	C14—N1—C4	122.3 (2)
C16—C17—C18	120.2 (3)	C7—N1—C4	117.9 (2)
C16—C17—H17	119.9	C14—N2—C13	116.1 (2)
C18—C17—H17	119.9	C21—N3—C22	117.0 (2)
C19—C18—C17	118.7 (3)	C21—N4—C28	119.3 (2)
C19—C18—H18	120.6	C21—N4—C29	122.7 (2)
C17—C18—H18	120.6	C28—N4—C29	117.8 (2)
C18—C19—C20	122.6 (2)	C14—O1—C15	116.9 (2)
C18—C19—O3	119.8 (2)	C21—O3—C19	116.43 (19)
C6—C1—C2—C3	−1.5 (5)	C34—C29—C30—C31	0.5 (4)
Cl1—C1—C2—C3	179.2 (3)	N4—C29—C30—C31	177.5 (3)
C1—C2—C3—C4	0.7 (5)	C29—C30—C31—C32	−1.3 (5)
C2—C3—C4—C5	0.8 (5)	C30—C31—C32—C33	1.0 (5)
C2—C3—C4—N1	−175.6 (3)	C30—C31—C32—Cl2	−178.9 (2)
C3—C4—C5—C6	−1.5 (5)	C31—C32—C33—C34	0.0 (5)
N1—C4—C5—C6	174.9 (3)	Cl2—C32—C33—C34	180.0 (3)
C4—C5—C6—C1	0.7 (5)	C32—C33—C34—C29	−0.8 (5)
C2—C1—C6—C5	0.9 (5)	C30—C29—C34—C33	0.5 (4)
Cl1—C1—C6—C5	−179.9 (2)	N4—C29—C34—C33	−176.5 (3)
O2—C7—C8—C9	1.0 (5)	N2—C14—N1—C7	−12.6 (4)
N1—C7—C8—C9	177.5 (3)	O1—C14—N1—C7	168.3 (2)
O2—C7—C8—C13	−175.6 (3)	N2—C14—N1—C4	170.8 (3)
N1—C7—C8—C13	1.0 (4)	O1—C14—N1—C4	−8.3 (3)
C13—C8—C9—C10	2.1 (5)	O2—C7—N1—C14	−174.7 (3)
C7—C8—C9—C10	−174.3 (3)	C8—C7—N1—C14	8.7 (4)
C8—C9—C10—C11	−0.2 (6)	O2—C7—N1—C4	2.1 (4)
C9—C10—C11—C12	−1.0 (6)	C8—C7—N1—C4	−174.6 (2)
C10—C11—C12—C13	0.3 (5)	C5—C4—N1—C14	112.2 (3)
C9—C8—C13—N2	174.8 (3)	C3—C4—N1—C14	−71.4 (3)
C7—C8—C13—N2	−8.7 (4)	C5—C4—N1—C7	−64.5 (4)
C9—C8—C13—C12	−2.8 (4)	C3—C4—N1—C7	112.0 (3)
C7—C8—C13—C12	173.8 (3)	O1—C14—N2—C13	−176.1 (2)
C11—C12—C13—N2	−176.1 (3)	N1—C14—N2—C13	4.8 (4)
C11—C12—C13—C8	1.6 (5)	C8—C13—N2—C14	6.0 (4)
C20—C15—C16—C17	−0.2 (4)	C12—C13—N2—C14	−176.5 (3)
O1—C15—C16—C17	173.9 (2)	O3—C21—N3—C22	176.2 (2)
C15—C16—C17—C18	0.1 (4)	N4—C21—N3—C22	−2.9 (4)
C16—C17—C18—C19	−0.2 (4)	C23—C22—N3—C21	177.8 (3)
C17—C18—C19—C20	0.3 (4)	C27—C22—N3—C21	−2.5 (4)
C17—C18—C19—O3	−175.2 (2)	N3—C21—N4—C28	5.0 (4)
C16—C15—C20—C19	0.3 (4)	O3—C21—N4—C28	−174.2 (2)
O1—C15—C20—C19	−174.0 (2)	N3—C21—N4—C29	−169.8 (3)
C18—C19—C20—C15	−0.3 (4)	O3—C21—N4—C29	11.0 (3)
O3—C19—C20—C15	175.3 (2)	O4—C28—N4—C21	−178.0 (3)
C27—C22—C23—C24	−2.5 (4)	C27—C28—N4—C21	−1.5 (4)
N3—C22—C23—C24	177.2 (3)	O4—C28—N4—C29	−2.9 (4)
C22—C23—C24—C25	0.8 (5)	C27—C28—N4—C29	173.5 (2)
C23—C24—C25—C26	0.7 (5)	C34—C29—N4—C21	−130.7 (3)
C24—C25—C26—C27	−0.5 (5)	C30—C29—N4—C21	52.3 (4)
C23—C22—C27—C26	2.7 (4)	C34—C29—N4—C28	54.4 (4)
N3—C22—C27—C26	−177.0 (3)	C30—C29—N4—C28	−122.6 (3)
C23—C22—C27—C28	−174.8 (3)	N2—C14—O1—C15	5.8 (4)
N3—C22—C27—C28	5.5 (4)	N1—C14—O1—C15	−175.0 (2)
C25—C26—C27—C22	−1.2 (4)	C20—C15—O1—C14	−103.7 (3)
C25—C26—C27—C28	176.3 (3)	C16—C15—O1—C14	82.0 (3)
C22—C27—C28—O4	173.0 (3)	N3—C21—O3—C19	20.3 (4)
C26—C27—C28—O4	−4.5 (4)	N4—C21—O3—C19	−160.5 (2)
C22—C27—C28—N4	−3.3 (4)	C18—C19—O3—C21	−98.9 (3)
C26—C27—C28—N4	179.3 (2)	C20—C19—O3—C21	85.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O2i	0.93	2.34	3.234 (3)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O2i	0.93	2.34	3.234 (3)	162

Symmetry code: (i) .