3,3′-Bis(4-chloro­phen­yl)-2,2′-(m-phenyl­enedi­oxy)diquinazolin-4(3H)-one

In the title compound, C₃₄H₂₀Cl₂N₄O₄, the two quinazoline heterocyclic systems and the adjacent chloro­benzene 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. Inter­molecular C—H...O hydrogen bonds contribute to the stability of the structure. In addition, weak π–π stacking inter­actions [centroid-to-centroid distances = 3.872 (1) and 3.876 (1) Å] are observed in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.066
• wR factor = 0.160
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C
            Value of measurement temperature given =   296.000
            Value of melting point given =     0.000
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C32
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT432_ALERT_2_C Short Inter X...Y Contact  O4     ..  C14     ..       2.94 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Quinazoline derivatives have broad biological properties. Some of these activities include antimicrobial (Pandeya et al., 1999; Shiba et al., 1997), antidiabetic (Malamas & Millen, 1991), anticonvulsant (Mannschreck et al., 1984), antibacterial (Kung et al., 1999), antifungal (Bartroli et al., 1998), protein tyrosine kinase inhibitors (Palmer et al., 1997), EGFR inhibitors (Tsou et al., 2001) and PDGFR phosphorylation inhibitors (Matsuno et al., 2002). We have recently focused on the synthesis of heterocyclic compounds using an aza-Wittig reaction. We present here the synthesis and the crystal structure of the title compound, (I) (Fig. 1), which can be used as a precursor for obtaining bioactive molecules.

In the crystal structure of (I), the quinazoline heterocycle N1—C7/C8–C13/N2—C14 and N3—C22/C23–C28/N4—C21 and the adjacent chlorobenzene ring C1–C6 and C29–C34 are not co-planar, but oriented at the dihedral angles of 66.66 (13) and 52.48 (12)°, respectively. The nearly planar quinazoline ring system N1—C7/C8–C13/N2—C14 and N3—C22/C23–C28/N4—C21 are oriented with respect to the adjacent ring C15–C20 at the dihedral angles of 79.73 (13) and 83.52 (13)°, respectively.

Significant intramolecular C—H···O hydrogen bonds contribute to the stability of the molecular configuration (Fig. 2 and Table 1). The crystal structure (Fig. 2) is also stabilized by weak π–π (Table 1) stacking interactions with centroid–centroid separations of 3.872 (1) and 3.876 (1) Å for Cg2···Cg2ⁱ and Cg2···Cg6ⁱ, respectively, where Cg2 and Cg6 are the centroids of rings N3/C21—N4/C28—C27/C22 and C22–C27, respectively [symmetry code: (i) 1 - x, -y, 1 - z].

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); Hu et al. (2006); Qu et al. (2008); Zeng et al. (2008); Sun et al. (2008).

S2. Experimental

To a solution of iminophosphorane (1.40 g, 3.0 mmol) in anhydrous THF (10 ml) was added 4-chlorophenyl isocyanate (3 mmol) under nitrogen at room temperature. After reaction, the mixture was allowed to stand for 10 h at 273–278 K, the solvent was removed under reduced pressure and diethyl ether/petroleum ether (1:2 v/v, 20 ml) was added to precipitate triphenylphosphine oxide. After filtration, the solvent was removed to give 1-(4-chlorophenyl)-3-(2-ethoxycarbonylphenyl) carbodiimide, which was used directly without further purification. To a solution of 1-(4-chlorophenyl)-3-(2-ethoxycarbonylphenyl) carbodiimide in THF (15 ml) was added m-dihydroxybenzene (0.18 g, 3 mmol). After the reaction mixture was allowed to stand for 0.5 h, the solvent was removed and anhydrous ethanol (10 ml) with several drops of EtONa in EtOH was added. The mixture was stirred for 2 h at room temperature. The solution was concentrated under reduced pressure and the residue was recrystallized from ethanol to give the title compound, (I). The product was recrystallized from methanol–dichloromethane (1:1 v/v, 20 ml) at room temperature to give crystals suitable for X-ray diffraction [m.p. 444 K, yield 45%].

S3. Refinement

All H atoms were located in difference maps and treated as riding atoms with C—H = 0.93 Å, U_iso = 1.2U_eq(C) for Csp².

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008).

Figures

	Fig. 1. View of the molecular structure of (I), showing the atom labelling scheme and with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A partial view of the crystal packing of (I), showing the formation of C—H···O hydrogen-bonds, as dashed lines.

3,3'-Bis(4-chlorophenyl)-2,2'-(m-phenylenedioxy)diquinazolin- 4(3H)-one

Crystal data

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) Å^3	0.23 × 0.10 × 0.10 mm
Z = 8

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3432 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.069
Graphite monochromator	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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.160	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0656P)^2] where P = (Fo^2 + 2Fc^2)/3
6251 reflections	(Δ/σ)max < 0.001
397 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O2^i	0.93	2.34	3.234 (3)	162

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.