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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): o59–o60.
Published online 2008 December 10. doi:  10.1107/S1600536808040567
PMCID: PMC2967973

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

Abstract

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.

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 [triangle]); Shiba et al. (1997 [triangle]); Malamas & Millen (1991 [triangle]); Mannschreck et al. (1984 [triangle]); Kung et al. (1999 [triangle]); Bartroli et al. (1998 [triangle]); Palmer et al. (1997 [triangle]); Tsou et al. (2001 [triangle]); Matsuno et al. (2002 [triangle]). For the synthesis, see: Yang et al. (2008 [triangle]). For related structures, see: Hu et al. (2006 [triangle]); Qu et al. (2008 [triangle]); Zeng et al. (2008 [triangle]); Sun et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-00o59-scheme1.jpg

Experimental

Crystal data

  • C34H20Cl2N4O4
  • M r = 619.44
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-00o59-efi1.jpg
  • 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 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

The authors are grateful to Xianning College for financial support of this work and providing laboratory and analytical facilities. The authors also acknowledge the Sophisticated Analytical Instrument Facility, Central China Normal University, Whuhan, for the data collection.

supplementary crystallographic information

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].

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%].

Refinement

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

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.

Crystal data

C34H20Cl2N4O4F(000) = 2544
Mr = 619.44Dx = 1.426 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1972 reflections
a = 28.043 (2) Åθ = 2.3–19.8°
b = 11.3563 (8) ŵ = 0.27 mm1
c = 21.5497 (16) ÅT = 296 K
β = 122.744 (1)°Block, colourless
V = 5772.2 (7) Å30.23 × 0.10 × 0.10 mm
Z = 8

Data collection

Bruker SMART APEX CCD area-detector diffractometer3432 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.069
graphiteθmax = 27.0°, θmin = 1.7°
[var phi] and ω scansh = −35→35
22711 measured reflectionsk = −14→14
6251 independent reflectionsl = −26→27

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0656P)2] where P = (Fo2 + 2Fc2)/3
6251 reflections(Δ/σ)max < 0.001
397 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = −0.28 e Å3

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 (Å2)

xyzUiso*/Ueq
C10.15141 (12)0.7594 (3)0.30121 (18)0.0559 (9)
C20.16014 (13)0.6517 (3)0.28105 (19)0.0618 (9)
H20.13490.59020.27050.074*
C30.20679 (12)0.6352 (3)0.27648 (17)0.0562 (9)
H30.21300.56240.26230.067*
C40.24445 (11)0.7262 (3)0.29288 (15)0.0425 (7)
C50.23582 (12)0.8331 (3)0.31471 (17)0.0545 (8)
H50.26170.89380.32690.065*
C60.18899 (12)0.8510 (3)0.31871 (19)0.0615 (9)
H60.18280.92370.33300.074*
C70.29051 (12)0.7746 (3)0.22679 (17)0.0502 (8)
C80.33543 (12)0.7466 (3)0.21498 (16)0.0485 (8)
C90.33834 (15)0.8010 (3)0.15926 (19)0.0705 (10)
H90.31320.86130.13180.085*
C100.37794 (16)0.7665 (4)0.1447 (2)0.0827 (12)
H100.37960.80310.10730.099*
C110.41546 (16)0.6774 (4)0.1854 (2)0.0776 (12)
H110.44190.65360.17460.093*
C120.41441 (13)0.6231 (3)0.24197 (17)0.0597 (9)
H120.44010.56340.26910.072*
C130.37438 (11)0.6583 (3)0.25844 (16)0.0460 (7)
C140.33712 (11)0.6382 (2)0.32842 (15)0.0384 (7)
C150.38186 (11)0.5356 (2)0.44066 (15)0.0359 (7)
C160.43022 (11)0.5918 (2)0.49417 (16)0.0434 (7)
H160.43410.67280.49230.052*
C170.47308 (12)0.5260 (3)0.55090 (16)0.0510 (8)
H170.50610.56290.58760.061*
C180.46706 (11)0.4053 (3)0.55324 (15)0.0430 (7)
H180.49580.36040.59120.052*
C190.41816 (11)0.3536 (2)0.49879 (15)0.0346 (6)
C200.37475 (10)0.4164 (2)0.44153 (15)0.0362 (6)
H200.34180.37940.40480.043*
C210.42029 (10)0.1591 (2)0.46272 (15)0.0365 (6)
C220.46375 (11)0.1061 (2)0.40343 (15)0.0402 (7)
C230.49672 (11)0.1357 (3)0.37574 (16)0.0507 (8)
H230.50960.21260.38030.061*
C240.51062 (12)0.0527 (3)0.34157 (18)0.0626 (9)
H240.53320.07360.32380.075*
C250.49123 (13)−0.0619 (3)0.33343 (18)0.0616 (9)
H250.5011−0.11790.31080.074*
C260.45743 (11)−0.0925 (3)0.35886 (17)0.0532 (8)
H260.4441−0.16920.35310.064*
C270.44305 (10)−0.0085 (2)0.39337 (15)0.0388 (7)
C280.40453 (11)−0.0402 (3)0.41594 (16)0.0432 (7)
C290.35068 (11)0.0301 (2)0.46823 (15)0.0404 (7)
C300.30465 (12)0.1049 (3)0.44078 (17)0.0490 (8)
H300.30160.17040.41290.059*
C310.26329 (13)0.0809 (3)0.45527 (19)0.0628 (9)
H310.23250.13150.43790.075*
C320.26727 (14)−0.0164 (3)0.4949 (2)0.0614 (9)
C330.31256 (14)−0.0906 (3)0.52176 (18)0.0628 (9)
H330.3150−0.15680.54870.075*
C340.35451 (12)−0.0670 (3)0.50883 (16)0.0516 (8)
H340.3856−0.11700.52760.062*
Cl10.09206 (4)0.78360 (10)0.30638 (6)0.0883 (4)
Cl20.21428 (5)−0.04566 (12)0.51094 (7)0.1140 (5)
N10.29124 (9)0.7099 (2)0.28274 (13)0.0414 (6)
N20.37633 (9)0.6075 (2)0.31840 (12)0.0417 (6)
N30.45216 (9)0.19030 (19)0.44073 (12)0.0405 (6)
N40.39348 (9)0.05110 (19)0.45116 (12)0.0384 (6)
O10.33518 (7)0.60201 (16)0.38599 (10)0.0447 (5)
O20.25236 (9)0.8446 (2)0.18965 (12)0.0715 (7)
O30.40913 (7)0.23167 (15)0.50289 (10)0.0408 (5)
O40.38040 (9)−0.13455 (18)0.40336 (13)0.0649 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0412 (16)0.061 (2)0.063 (2)0.0031 (16)0.0265 (16)0.0035 (18)
C20.0488 (18)0.049 (2)0.082 (3)−0.0122 (16)0.0319 (18)−0.0058 (19)
C30.0533 (18)0.0416 (19)0.068 (2)−0.0043 (16)0.0293 (17)−0.0063 (17)
C40.0335 (14)0.0388 (18)0.0436 (18)0.0036 (13)0.0132 (13)0.0048 (14)
C50.0429 (17)0.043 (2)0.069 (2)−0.0033 (15)0.0247 (16)−0.0038 (17)
C60.0452 (17)0.047 (2)0.082 (3)0.0029 (16)0.0282 (17)−0.0100 (18)
C70.0454 (17)0.048 (2)0.0401 (19)−0.0037 (15)0.0117 (15)0.0051 (16)
C80.0494 (17)0.051 (2)0.0359 (18)−0.0070 (15)0.0172 (15)0.0045 (15)
C90.069 (2)0.081 (3)0.052 (2)−0.010 (2)0.0263 (19)0.013 (2)
C100.072 (2)0.123 (4)0.054 (2)−0.017 (3)0.035 (2)0.006 (3)
C110.075 (2)0.110 (4)0.062 (3)−0.016 (2)0.046 (2)−0.013 (2)
C120.0563 (19)0.074 (3)0.051 (2)−0.0059 (17)0.0307 (17)−0.0092 (18)
C130.0439 (16)0.050 (2)0.0389 (18)−0.0101 (14)0.0189 (14)−0.0082 (15)
C140.0393 (15)0.0325 (17)0.0362 (17)−0.0018 (13)0.0158 (13)0.0015 (13)
C150.0382 (14)0.0334 (17)0.0399 (17)0.0063 (13)0.0235 (13)0.0072 (14)
C160.0502 (17)0.0269 (16)0.0521 (19)−0.0039 (13)0.0270 (15)−0.0011 (14)
C170.0451 (17)0.043 (2)0.047 (2)−0.0094 (14)0.0135 (15)−0.0039 (16)
C180.0419 (16)0.0392 (18)0.0384 (17)0.0024 (13)0.0156 (14)0.0055 (14)
C190.0432 (15)0.0255 (15)0.0422 (17)−0.0030 (12)0.0278 (14)−0.0001 (13)
C200.0329 (14)0.0360 (17)0.0365 (16)−0.0042 (12)0.0167 (12)−0.0052 (13)
C210.0370 (14)0.0288 (16)0.0414 (17)0.0008 (12)0.0197 (13)−0.0009 (13)
C220.0365 (14)0.0397 (18)0.0420 (17)−0.0023 (13)0.0197 (13)−0.0031 (14)
C230.0518 (17)0.052 (2)0.054 (2)−0.0095 (15)0.0329 (16)−0.0074 (16)
C240.0541 (19)0.082 (3)0.063 (2)−0.0146 (19)0.0385 (18)−0.018 (2)
C250.0528 (18)0.069 (2)0.067 (2)0.0015 (18)0.0351 (18)−0.018 (2)
C260.0444 (16)0.048 (2)0.064 (2)−0.0031 (15)0.0278 (16)−0.0148 (17)
C270.0325 (14)0.0362 (17)0.0429 (17)−0.0004 (12)0.0171 (13)−0.0052 (14)
C280.0417 (15)0.0326 (17)0.0532 (19)0.0014 (14)0.0243 (14)−0.0015 (15)
C290.0385 (15)0.0370 (17)0.0476 (18)−0.0055 (13)0.0247 (14)−0.0008 (15)
C300.0478 (16)0.0437 (19)0.060 (2)0.0019 (15)0.0320 (16)0.0043 (16)
C310.0513 (19)0.066 (2)0.079 (3)0.0040 (17)0.0404 (19)−0.005 (2)
C320.065 (2)0.070 (3)0.071 (2)−0.0168 (19)0.051 (2)−0.011 (2)
C330.073 (2)0.066 (2)0.058 (2)−0.013 (2)0.0403 (19)0.0077 (19)
C340.0539 (18)0.046 (2)0.052 (2)0.0009 (15)0.0267 (16)0.0093 (16)
Cl10.0611 (5)0.0904 (8)0.1270 (9)0.0016 (5)0.0599 (6)−0.0005 (7)
Cl20.1066 (8)0.1518 (12)0.1397 (11)−0.0316 (8)0.1032 (8)−0.0167 (9)
N10.0382 (12)0.0372 (14)0.0401 (14)0.0015 (11)0.0156 (11)0.0056 (12)
N20.0447 (13)0.0413 (15)0.0408 (14)0.0015 (11)0.0243 (12)0.0008 (12)
N30.0452 (13)0.0337 (14)0.0461 (15)−0.0044 (11)0.0271 (12)−0.0036 (12)
N40.0415 (12)0.0280 (13)0.0506 (15)−0.0043 (10)0.0280 (12)−0.0044 (11)
O10.0427 (10)0.0424 (12)0.0497 (12)0.0110 (9)0.0255 (10)0.0148 (10)
O20.0596 (13)0.0775 (17)0.0605 (15)0.0203 (13)0.0214 (12)0.0328 (14)
O30.0572 (11)0.0245 (10)0.0509 (13)−0.0027 (9)0.0358 (10)−0.0013 (9)
O40.0691 (14)0.0408 (13)0.1020 (19)−0.0178 (11)0.0576 (14)−0.0200 (13)

Geometric parameters (Å, °)

C1—C21.364 (4)C17—H170.9300
C1—C61.380 (4)C18—C191.365 (4)
C1—Cl11.749 (3)C18—H180.9300
C2—C31.377 (4)C19—C201.374 (3)
C2—H20.9300C19—O31.419 (3)
C3—C41.380 (4)C20—H200.9300
C3—H30.9300C21—N31.268 (3)
C4—C51.370 (4)C21—O31.349 (3)
C4—N11.454 (3)C21—N41.389 (3)
C5—C61.377 (4)C22—C231.386 (4)
C5—H50.9300C22—C271.394 (4)
C6—H60.9300C22—N31.396 (3)
C7—O21.221 (3)C23—C241.376 (4)
C7—N11.402 (4)C23—H230.9300
C7—C81.449 (4)C24—C251.384 (4)
C8—C91.392 (4)C24—H240.9300
C8—C131.403 (4)C25—C261.372 (4)
C9—C101.364 (5)C25—H250.9300
C9—H90.9300C26—C271.396 (4)
C10—C111.379 (5)C26—H260.9300
C10—H100.9300C27—C281.450 (4)
C11—C121.380 (5)C28—O41.217 (3)
C11—H110.9300C28—N41.415 (3)
C12—C131.406 (4)C29—C341.376 (4)
C12—H120.9300C29—C301.382 (4)
C13—N21.389 (3)C29—N41.453 (3)
C14—N21.278 (3)C30—C311.381 (4)
C14—O11.336 (3)C30—H300.9300
C14—N11.385 (3)C31—C321.364 (5)
C15—C201.370 (4)C31—H310.9300
C15—C161.372 (4)C32—C331.364 (5)
C15—O11.415 (3)C32—Cl21.730 (3)
C16—C171.381 (4)C33—C341.374 (4)
C16—H160.9300C33—H330.9300
C17—C181.385 (4)C34—H340.9300
C2—C1—C6121.4 (3)C20—C19—O3117.5 (2)
C2—C1—Cl1120.1 (3)C15—C20—C19117.4 (2)
C6—C1—Cl1118.5 (3)C15—C20—H20121.3
C1—C2—C3119.0 (3)C19—C20—H20121.3
C1—C2—H2120.5N3—C21—O3121.6 (2)
C3—C2—H2120.5N3—C21—N4127.1 (2)
C2—C3—C4120.4 (3)O3—C21—N4111.3 (2)
C2—C3—H3119.8C23—C22—C27118.6 (3)
C4—C3—H3119.8C23—C22—N3119.9 (3)
C5—C4—C3119.9 (3)C27—C22—N3121.5 (2)
C5—C4—N1120.4 (3)C24—C23—C22120.8 (3)
C3—C4—N1119.6 (3)C24—C23—H23119.6
C4—C5—C6120.3 (3)C22—C23—H23119.6
C4—C5—H5119.9C23—C24—C25120.4 (3)
C6—C5—H5119.9C23—C24—H24119.8
C5—C6—C1119.0 (3)C25—C24—H24119.8
C5—C6—H6120.5C26—C25—C24119.8 (3)
C1—C6—H6120.5C26—C25—H25120.1
O2—C7—N1120.3 (3)C24—C25—H25120.1
O2—C7—C8124.4 (3)C25—C26—C27120.0 (3)
N1—C7—C8115.2 (3)C25—C26—H26120.0
C9—C8—C13120.4 (3)C27—C26—H26120.0
C9—C8—C7121.1 (3)C22—C27—C26120.3 (3)
C13—C8—C7118.5 (3)C22—C27—C28120.2 (2)
C10—C9—C8120.3 (4)C26—C27—C28119.4 (3)
C10—C9—H9119.8O4—C28—N4120.5 (3)
C8—C9—H9119.8O4—C28—C27124.7 (3)
C9—C10—C11120.0 (4)N4—C28—C27114.6 (2)
C9—C10—H10120.0C34—C29—C30119.9 (3)
C11—C10—H10120.0C34—C29—N4120.1 (2)
C10—C11—C12121.1 (3)C30—C29—N4119.9 (2)
C10—C11—H11119.5C31—C30—C29119.1 (3)
C12—C11—H11119.5C31—C30—H30120.5
C11—C12—C13119.8 (3)C29—C30—H30120.5
C11—C12—H12120.1C32—C31—C30120.5 (3)
C13—C12—H12120.1C32—C31—H31119.8
N2—C13—C8122.8 (3)C30—C31—H31119.8
N2—C13—C12118.8 (3)C31—C32—C33120.5 (3)
C8—C13—C12118.3 (3)C31—C32—Cl2119.5 (3)
N2—C14—O1123.0 (2)C33—C32—Cl2120.0 (3)
N2—C14—N1126.4 (3)C32—C33—C34119.8 (3)
O1—C14—N1110.6 (2)C32—C33—H33120.1
C20—C15—C16122.2 (3)C34—C33—H33120.1
C20—C15—O1117.5 (2)C33—C34—C29120.3 (3)
C16—C15—O1120.1 (2)C33—C34—H34119.9
C15—C16—C17118.9 (3)C29—C34—H34119.9
C15—C16—H16120.5C14—N1—C7119.7 (2)
C17—C16—H16120.5C14—N1—C4122.3 (2)
C16—C17—C18120.2 (3)C7—N1—C4117.9 (2)
C16—C17—H17119.9C14—N2—C13116.1 (2)
C18—C17—H17119.9C21—N3—C22117.0 (2)
C19—C18—C17118.7 (3)C21—N4—C28119.3 (2)
C19—C18—H18120.6C21—N4—C29122.7 (2)
C17—C18—H18120.6C28—N4—C29117.8 (2)
C18—C19—C20122.6 (2)C14—O1—C15116.9 (2)
C18—C19—O3119.8 (2)C21—O3—C19116.43 (19)
C6—C1—C2—C3−1.5 (5)C34—C29—C30—C310.5 (4)
Cl1—C1—C2—C3179.2 (3)N4—C29—C30—C31177.5 (3)
C1—C2—C3—C40.7 (5)C29—C30—C31—C32−1.3 (5)
C2—C3—C4—C50.8 (5)C30—C31—C32—C331.0 (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—C340.0 (5)
N1—C4—C5—C6174.9 (3)Cl2—C32—C33—C34180.0 (3)
C4—C5—C6—C10.7 (5)C32—C33—C34—C29−0.8 (5)
C2—C1—C6—C50.9 (5)C30—C29—C34—C330.5 (4)
Cl1—C1—C6—C5−179.9 (2)N4—C29—C34—C33−176.5 (3)
O2—C7—C8—C91.0 (5)N2—C14—N1—C7−12.6 (4)
N1—C7—C8—C9177.5 (3)O1—C14—N1—C7168.3 (2)
O2—C7—C8—C13−175.6 (3)N2—C14—N1—C4170.8 (3)
N1—C7—C8—C131.0 (4)O1—C14—N1—C4−8.3 (3)
C13—C8—C9—C102.1 (5)O2—C7—N1—C14−174.7 (3)
C7—C8—C9—C10−174.3 (3)C8—C7—N1—C148.7 (4)
C8—C9—C10—C11−0.2 (6)O2—C7—N1—C42.1 (4)
C9—C10—C11—C12−1.0 (6)C8—C7—N1—C4−174.6 (2)
C10—C11—C12—C130.3 (5)C5—C4—N1—C14112.2 (3)
C9—C8—C13—N2174.8 (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—C7112.0 (3)
C7—C8—C13—C12173.8 (3)O1—C14—N2—C13−176.1 (2)
C11—C12—C13—N2−176.1 (3)N1—C14—N2—C134.8 (4)
C11—C12—C13—C81.6 (5)C8—C13—N2—C146.0 (4)
C20—C15—C16—C17−0.2 (4)C12—C13—N2—C14−176.5 (3)
O1—C15—C16—C17173.9 (2)O3—C21—N3—C22176.2 (2)
C15—C16—C17—C180.1 (4)N4—C21—N3—C22−2.9 (4)
C16—C17—C18—C19−0.2 (4)C23—C22—N3—C21177.8 (3)
C17—C18—C19—C200.3 (4)C27—C22—N3—C21−2.5 (4)
C17—C18—C19—O3−175.2 (2)N3—C21—N4—C285.0 (4)
C16—C15—C20—C190.3 (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—C2911.0 (3)
O3—C19—C20—C15175.3 (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—C24177.2 (3)O4—C28—N4—C29−2.9 (4)
C22—C23—C24—C250.8 (5)C27—C28—N4—C29173.5 (2)
C23—C24—C25—C260.7 (5)C34—C29—N4—C21−130.7 (3)
C24—C25—C26—C27−0.5 (5)C30—C29—N4—C2152.3 (4)
C23—C22—C27—C262.7 (4)C34—C29—N4—C2854.4 (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—C155.8 (4)
N3—C22—C27—C285.5 (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—C28176.3 (3)C16—C15—O1—C1482.0 (3)
C22—C27—C28—O4173.0 (3)N3—C21—O3—C1920.3 (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—N4179.3 (2)C20—C19—O3—C2185.4 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C20—H20···O2i0.932.343.234 (3)162

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2685).

References

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