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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): o2522.
Published online 2010 September 8. doi:  10.1107/S1600536810035324
PMCID: PMC2983302

2-Anilino-3-(2-hy­droxy­phen­yl)quinazolin-4(3H)-one–triphenyl­phosphine oxide (1/1)

Abstract

In the title compound, C20H15N3O2·C18H15OP, the pyrimidinone heterocycle and the fused phenyl ring are inclined at 1.92 (7)°. Only the hy­droxy group is involved in hydrogen bonding, whereas the amino group is shielded from potential acceptors.

Related literature

For the synthesis of the title compound, see: Yang et al. (2008 [triangle]).

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Object name is e-66-o2522-scheme1.jpg

Experimental

Crystal data

  • C20H15N3O2·C18H15OP
  • M r = 607.62
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2522-efi1.jpg
  • a = 18.9139 (3) Å
  • b = 10.3201 (2) Å
  • c = 18.2145 (3) Å
  • β = 117.771 (1)°
  • V = 3145.83 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.13 mm−1
  • T = 298 K
  • 0.16 × 0.12 × 0.10 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2001 [triangle]) T min = 0.980, T max = 0.987
  • 38085 measured reflections
  • 7826 independent reflections
  • 5767 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.134
  • S = 1.01
  • 7826 reflections
  • 412 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.37 e Å−3
  • Δρmin = −0.23 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/S1600536810035324/bt5345sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035324/bt5345Isup2.hkl

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

Acknowledgments

The authors are grateful to Hubei Medical University Education Committee (grant No. 2009QJ12) for financial support and acknowledge the Sophisticated Analytical Instrument Facility, Central China Normal University, Wuhan, for the data collection.

supplementary crystallographic information

Comment

Quinazoline-4(3H)-one derivatives have numerous biological properties. We have recently focused on the synthesis of heterocyclic compounds using an aza-Wittig reaction. We present here the crystal structure of the title compound (Fig. 1), which can be used as a precursor for obtaining bioactive molecules.

In the crystal structure, the pyrimidinone heterocycle and the adjacent benzene ring are not coplanar, but inclined at 1.92 (7) °. Only the hydroxyl group is involved in hydrogen bonding, whereas the amino group is shielded from potential acceptors.

Experimental

To a solution of iminophosphorane (1.40 g, 3.0 mmol) in anhydrous THF (10 ml) was added isocyanatobenzene (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-phenyl- 3-(2-ethoxycarbonylphenyl) carbodiimide, which was used directly without further purification. To a solution of 1-phenyl- 3-(2-ethoxycarbonylphenyl) carbodiimide in THF (15 ml) was added 2-aminophenol (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 (yield 79%).

Refinement

All the carbon-bonded hydrogen atoms set to ideal positons with C—H = 0.93Å (aromatic) and 0.96Å (methyl), and Uiso(H) = 1.2UeqC for aromatic and 1.5 UeqC for methyl hydrogen atoms, respectively. H atoms bonded to N and O atoms were found in a difference map and then refined with distance restraints of N—H = 0.85 (2)Å and O—H = 0.90 (2) Å. The displacement parameters were set Uiso(H) = 1.2UeqN or Uiso(H) = 1.5UeqO.

Figures

Fig. 1.
View of the molecular structure of the title compound, showing the atom labelling schemeand with displacement ellipsoids drawn at the 50% probability level.

Crystal data

C20H15N3O2·C18H15OPF(000) = 1272
Mr = 607.62Dx = 1.283 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 18.9139 (3) ÅCell parameters from 5201 reflections
b = 10.3201 (2) Åθ = 2.3–26.1°
c = 18.2145 (3) ŵ = 0.13 mm1
β = 117.771 (1)°T = 298 K
V = 3145.83 (9) Å3Block, colorless
Z = 40.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer7826 independent reflections
Radiation source: fine-focus sealed tube5767 reflections with I > 2σ(I)
graphiteRint = 0.036
[var phi] and ω scansθmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)h = −25→25
Tmin = 0.980, Tmax = 0.987k = −13→13
38085 measured reflectionsl = −24→24

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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.0807P)2] where P = (Fo2 + 2Fc2)/3
7826 reflections(Δ/σ)max = 0.001
412 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = −0.23 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
C10.32962 (8)0.72741 (14)0.53651 (9)0.0427 (3)
C20.40582 (9)0.67312 (16)0.56734 (10)0.0553 (4)
H20.44660.71940.56440.066*
C30.42037 (10)0.55219 (17)0.60173 (12)0.0648 (5)
H30.47100.51600.62190.078*
C40.35995 (10)0.48339 (18)0.60672 (12)0.0698 (5)
H40.37030.40120.63030.084*
C50.28496 (10)0.53564 (16)0.57706 (11)0.0602 (4)
H50.24500.48910.58150.072*
C60.26804 (8)0.65830 (13)0.54015 (9)0.0438 (3)
C70.31351 (8)0.85644 (13)0.50056 (9)0.0431 (3)
C80.17650 (8)0.81807 (13)0.47432 (9)0.0407 (3)
C90.03094 (8)0.81895 (13)0.43622 (9)0.0426 (3)
C10−0.03180 (9)0.90485 (15)0.41509 (11)0.0573 (4)
H10−0.02560.99110.40440.069*
C11−0.10340 (9)0.86384 (17)0.40972 (12)0.0651 (5)
H11−0.14510.92250.39530.078*
C12−0.11359 (9)0.73755 (17)0.42540 (11)0.0588 (4)
H12−0.16140.71040.42330.071*
C13−0.05256 (9)0.65174 (16)0.44417 (11)0.0579 (4)
H13−0.05990.56530.45340.069*
C140.01986 (9)0.69020 (14)0.44979 (10)0.0533 (4)
H140.06070.63030.46250.064*
C150.21124 (8)1.01666 (14)0.42224 (9)0.0435 (3)
C160.22674 (8)1.13421 (14)0.46389 (9)0.0444 (3)
C170.20183 (10)1.24752 (16)0.41711 (11)0.0595 (4)
H170.21151.32730.44390.071*
C180.16332 (11)1.2428 (2)0.33218 (12)0.0701 (5)
H180.14671.31940.30200.084*
C190.14897 (11)1.1270 (2)0.29119 (11)0.0762 (6)
H190.12291.12470.23350.091*
C200.17354 (10)1.01345 (18)0.33622 (10)0.0642 (5)
H200.16480.93450.30870.077*
C210.33743 (8)0.43284 (13)0.30104 (9)0.0433 (3)
C220.32238 (9)0.31200 (15)0.26340 (11)0.0537 (4)
H220.29730.30580.20580.064*
C230.34463 (11)0.20058 (16)0.31131 (13)0.0675 (5)
H230.33500.11990.28580.081*
C240.38093 (11)0.20870 (18)0.39657 (13)0.0674 (5)
H240.39440.13370.42850.081*
C250.39715 (11)0.32773 (18)0.43414 (11)0.0649 (5)
H250.42240.33320.49170.078*
C260.37629 (10)0.43949 (16)0.38725 (10)0.0554 (4)
H260.38830.51980.41340.066*
C270.37978 (8)0.69513 (13)0.28300 (8)0.0409 (3)
C280.43786 (9)0.70114 (15)0.25692 (10)0.0523 (4)
H280.43480.64660.21490.063*
C290.50034 (10)0.78835 (18)0.29339 (11)0.0636 (5)
H290.53880.79290.27530.076*
C300.50577 (10)0.86780 (17)0.35592 (12)0.0649 (5)
H300.54830.92530.38070.078*
C310.44867 (11)0.86288 (16)0.38213 (11)0.0642 (5)
H310.45250.91700.42460.077*
C320.38546 (10)0.77778 (15)0.34559 (10)0.0542 (4)
H320.34640.77580.36300.065*
C330.21504 (8)0.63051 (13)0.24196 (9)0.0435 (3)
C340.19543 (10)0.59243 (16)0.30366 (10)0.0560 (4)
H340.23090.54140.34750.067*
C350.12366 (11)0.62987 (19)0.30023 (12)0.0677 (5)
H350.11110.60400.34170.081*
C360.07094 (11)0.70508 (19)0.23571 (13)0.0703 (5)
H360.02250.72920.23310.084*
C370.08972 (11)0.74456 (19)0.17519 (12)0.0687 (5)
H370.05410.79620.13190.082*
C380.16126 (10)0.70831 (16)0.17799 (10)0.0566 (4)
H380.17350.73620.13670.068*
N10.23328 (6)0.89554 (11)0.46688 (7)0.0402 (3)
N20.19109 (7)0.70555 (11)0.50893 (7)0.0443 (3)
H2A0.2741 (11)1.0768 (17)0.5709 (11)0.066*
N30.10191 (7)0.87046 (12)0.44097 (9)0.0511 (3)
H3A0.0993 (10)0.9481 (17)0.4256 (10)0.061*
O10.36237 (6)0.92844 (10)0.49659 (7)0.0590 (3)
O20.26529 (7)1.14642 (10)0.54705 (7)0.0558 (3)
O30.28491 (6)0.54813 (10)0.14922 (6)0.0496 (3)
P10.30304 (2)0.57484 (3)0.23650 (2)0.03965 (11)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0443 (7)0.0437 (7)0.0428 (7)−0.0029 (6)0.0226 (6)−0.0082 (6)
C20.0449 (8)0.0609 (10)0.0618 (10)−0.0022 (7)0.0263 (7)−0.0098 (8)
C30.0482 (9)0.0657 (11)0.0748 (12)0.0127 (8)0.0239 (8)0.0008 (9)
C40.0644 (11)0.0566 (10)0.0835 (13)0.0147 (9)0.0302 (10)0.0152 (9)
C50.0540 (9)0.0507 (9)0.0759 (12)0.0026 (7)0.0303 (8)0.0111 (8)
C60.0442 (8)0.0423 (7)0.0468 (8)−0.0011 (6)0.0226 (6)−0.0024 (6)
C70.0445 (7)0.0458 (8)0.0445 (8)−0.0081 (6)0.0254 (6)−0.0107 (6)
C80.0429 (7)0.0388 (7)0.0438 (7)−0.0043 (6)0.0232 (6)−0.0007 (6)
C90.0388 (7)0.0432 (7)0.0446 (8)−0.0023 (6)0.0184 (6)0.0051 (6)
C100.0484 (9)0.0459 (8)0.0730 (11)0.0036 (7)0.0244 (8)0.0139 (7)
C110.0433 (9)0.0594 (10)0.0887 (13)0.0088 (7)0.0275 (9)0.0123 (9)
C120.0394 (8)0.0653 (10)0.0691 (11)−0.0025 (7)0.0232 (7)0.0095 (8)
C130.0445 (8)0.0512 (9)0.0728 (11)−0.0035 (7)0.0230 (8)0.0146 (8)
C140.0440 (8)0.0436 (8)0.0712 (11)0.0032 (6)0.0259 (8)0.0116 (7)
C150.0447 (7)0.0448 (8)0.0429 (8)−0.0083 (6)0.0221 (6)0.0052 (6)
C160.0456 (8)0.0432 (7)0.0483 (8)−0.0051 (6)0.0251 (7)0.0046 (6)
C170.0643 (10)0.0459 (9)0.0711 (11)−0.0018 (7)0.0339 (9)0.0121 (8)
C180.0636 (11)0.0694 (12)0.0682 (12)−0.0042 (9)0.0230 (9)0.0301 (10)
C190.0767 (12)0.0890 (14)0.0466 (10)−0.0218 (11)0.0150 (9)0.0193 (10)
C200.0740 (11)0.0667 (11)0.0454 (9)−0.0251 (9)0.0225 (8)−0.0012 (8)
C210.0419 (7)0.0429 (7)0.0479 (8)−0.0008 (6)0.0234 (6)0.0042 (6)
C220.0565 (9)0.0459 (8)0.0599 (10)−0.0015 (7)0.0280 (8)0.0011 (7)
C230.0735 (12)0.0426 (9)0.0881 (14)0.0002 (8)0.0390 (10)0.0045 (9)
C240.0691 (11)0.0563 (10)0.0846 (13)0.0125 (9)0.0425 (10)0.0265 (10)
C250.0682 (11)0.0696 (12)0.0579 (10)0.0128 (9)0.0302 (9)0.0193 (9)
C260.0599 (9)0.0532 (9)0.0508 (9)0.0034 (7)0.0239 (8)0.0061 (7)
C270.0444 (7)0.0383 (7)0.0387 (7)−0.0001 (6)0.0183 (6)0.0031 (6)
C280.0530 (9)0.0566 (9)0.0520 (9)−0.0019 (7)0.0284 (7)0.0006 (7)
C290.0490 (9)0.0720 (11)0.0712 (11)−0.0074 (8)0.0290 (8)0.0096 (9)
C300.0546 (10)0.0534 (10)0.0680 (11)−0.0139 (8)0.0129 (8)0.0041 (8)
C310.0679 (11)0.0516 (9)0.0640 (11)−0.0091 (8)0.0229 (9)−0.0147 (8)
C320.0574 (9)0.0522 (9)0.0566 (9)−0.0057 (7)0.0296 (8)−0.0103 (7)
C330.0464 (8)0.0419 (7)0.0435 (8)−0.0069 (6)0.0221 (6)−0.0068 (6)
C340.0592 (9)0.0602 (10)0.0554 (9)−0.0022 (8)0.0325 (8)0.0006 (7)
C350.0703 (11)0.0755 (12)0.0774 (13)−0.0112 (10)0.0512 (10)−0.0132 (10)
C360.0534 (10)0.0749 (12)0.0870 (14)−0.0026 (9)0.0364 (10)−0.0225 (11)
C370.0588 (10)0.0724 (12)0.0669 (11)0.0149 (9)0.0227 (9)−0.0037 (9)
C380.0591 (10)0.0599 (10)0.0519 (9)0.0074 (8)0.0268 (8)0.0011 (7)
N10.0435 (6)0.0385 (6)0.0418 (6)−0.0074 (5)0.0226 (5)−0.0012 (5)
N20.0430 (6)0.0405 (6)0.0512 (7)−0.0007 (5)0.0235 (6)0.0052 (5)
N30.0448 (7)0.0408 (7)0.0697 (9)0.0007 (5)0.0283 (6)0.0152 (6)
O10.0520 (6)0.0544 (6)0.0810 (8)−0.0122 (5)0.0397 (6)−0.0026 (5)
O20.0792 (8)0.0408 (6)0.0485 (6)−0.0031 (5)0.0307 (6)−0.0003 (5)
O30.0628 (6)0.0483 (6)0.0400 (6)−0.0044 (5)0.0258 (5)−0.0055 (4)
P10.0454 (2)0.0385 (2)0.0372 (2)−0.00294 (15)0.02114 (16)−0.00170 (14)

Geometric parameters (Å, °)

C1—C61.3935 (19)C20—H200.9300
C1—C21.397 (2)C21—C221.387 (2)
C1—C71.452 (2)C21—C261.391 (2)
C2—C31.366 (2)C21—P11.8000 (14)
C2—H20.9300C22—C231.385 (2)
C3—C41.384 (2)C22—H220.9300
C3—H30.9300C23—C241.377 (3)
C4—C51.371 (2)C23—H230.9300
C4—H40.9300C24—C251.370 (3)
C5—C61.399 (2)C24—H240.9300
C5—H50.9300C25—C261.379 (2)
C6—N21.3812 (17)C25—H250.9300
C7—O11.2141 (16)C26—H260.9300
C7—N11.4050 (17)C27—C281.386 (2)
C8—N21.2884 (17)C27—C321.387 (2)
C8—N31.3612 (18)C27—P11.7944 (14)
C8—N11.3952 (16)C28—C291.384 (2)
C9—C101.384 (2)C28—H280.9300
C9—C141.3851 (19)C29—C301.368 (3)
C9—N31.4084 (17)C29—H290.9300
C10—C111.378 (2)C30—C311.370 (3)
C10—H100.9300C30—H300.9300
C11—C121.367 (2)C31—C321.379 (2)
C11—H110.9300C31—H310.9300
C12—C131.366 (2)C32—H320.9300
C12—H120.9300C33—C381.390 (2)
C13—C141.383 (2)C33—C341.394 (2)
C13—H130.9300C33—P11.8067 (15)
C14—H140.9300C34—C351.385 (2)
C15—C201.387 (2)C34—H340.9300
C15—C161.388 (2)C35—C361.373 (3)
C15—N11.4428 (17)C35—H350.9300
C16—O21.3463 (17)C36—C371.368 (3)
C16—C171.393 (2)C36—H360.9300
C17—C181.370 (2)C37—C381.382 (2)
C17—H170.9300C37—H370.9300
C18—C191.368 (3)C38—H380.9300
C18—H180.9300N3—H3A0.843 (17)
C19—C201.381 (2)O2—H2A0.815 (18)
C19—H190.9300O3—P11.4876 (10)
C6—C1—C2120.27 (14)C23—C22—H22119.9
C6—C1—C7119.10 (12)C21—C22—H22119.9
C2—C1—C7120.62 (13)C24—C23—C22120.36 (16)
C3—C2—C1120.03 (15)C24—C23—H23119.8
C3—C2—H2120.0C22—C23—H23119.8
C1—C2—H2120.0C25—C24—C23119.73 (16)
C2—C3—C4120.19 (15)C25—C24—H24120.1
C2—C3—H3119.9C23—C24—H24120.1
C4—C3—H3119.9C24—C25—C26120.52 (17)
C5—C4—C3120.44 (16)C24—C25—H25119.7
C5—C4—H4119.8C26—C25—H25119.7
C3—C4—H4119.8C25—C26—C21120.40 (16)
C4—C5—C6120.55 (15)C25—C26—H26119.8
C4—C5—H5119.7C21—C26—H26119.8
C6—C5—H5119.7C28—C27—C32118.93 (14)
N2—C6—C1122.91 (13)C28—C27—P1117.71 (11)
N2—C6—C5118.60 (13)C32—C27—P1123.30 (11)
C1—C6—C5118.49 (13)C29—C28—C27120.00 (15)
O1—C7—N1119.70 (13)C29—C28—H28120.0
O1—C7—C1125.62 (13)C27—C28—H28120.0
N1—C7—C1114.66 (11)C30—C29—C28120.37 (16)
N2—C8—N3121.17 (12)C30—C29—H29119.8
N2—C8—N1124.40 (12)C28—C29—H29119.8
N3—C8—N1114.44 (12)C29—C30—C31120.15 (15)
C10—C9—C14118.85 (13)C29—C30—H30119.9
C10—C9—N3116.38 (12)C31—C30—H30119.9
C14—C9—N3124.76 (13)C30—C31—C32120.15 (16)
C11—C10—C9120.65 (15)C30—C31—H31119.9
C11—C10—H10119.7C32—C31—H31119.9
C9—C10—H10119.7C31—C32—C27120.38 (15)
C12—C11—C10120.49 (15)C31—C32—H32119.8
C12—C11—H11119.8C27—C32—H32119.8
C10—C11—H11119.8C38—C33—C34118.22 (15)
C13—C12—C11119.05 (15)C38—C33—P1118.08 (11)
C13—C12—H12120.5C34—C33—P1123.54 (12)
C11—C12—H12120.5C35—C34—C33120.56 (17)
C12—C13—C14121.64 (15)C35—C34—H34119.7
C12—C13—H13119.2C33—C34—H34119.7
C14—C13—H13119.2C36—C35—C34120.14 (17)
C13—C14—C9119.27 (14)C36—C35—H35119.9
C13—C14—H14120.4C34—C35—H35119.9
C9—C14—H14120.4C37—C36—C35120.01 (17)
C20—C15—C16120.33 (14)C37—C36—H36120.0
C20—C15—N1118.52 (13)C35—C36—H36120.0
C16—C15—N1121.15 (12)C36—C37—C38120.46 (18)
O2—C16—C15124.23 (13)C36—C37—H37119.8
O2—C16—C17117.46 (14)C38—C37—H37119.8
C15—C16—C17118.31 (14)C37—C38—C33120.59 (16)
C18—C17—C16120.74 (16)C37—C38—H38119.7
C18—C17—H17119.6C33—C38—H38119.7
C16—C17—H17119.6C8—N1—C7121.11 (11)
C19—C18—C17120.90 (16)C8—N1—C15121.18 (11)
C19—C18—H18119.5C7—N1—C15117.69 (11)
C17—C18—H18119.5C8—N2—C6117.65 (12)
C18—C19—C20119.40 (17)C8—N3—C9129.60 (12)
C18—C19—H19120.3C8—N3—H3A114.5 (11)
C20—C19—H19120.3C9—N3—H3A115.5 (11)
C19—C20—C15120.29 (17)C16—O2—H2A112.7 (13)
C19—C20—H20119.9O3—P1—C27111.44 (6)
C15—C20—H20119.9O3—P1—C21112.35 (6)
C22—C21—C26118.76 (14)C27—P1—C21106.76 (6)
C22—C21—P1118.73 (12)O3—P1—C33110.99 (6)
C26—C21—P1122.49 (11)C27—P1—C33108.51 (6)
C23—C22—C21120.18 (16)C21—P1—C33106.55 (7)
C6—C1—C2—C3−0.4 (2)C28—C27—C32—C31−1.1 (2)
C7—C1—C2—C3179.35 (14)P1—C27—C32—C31176.10 (12)
C1—C2—C3—C4−0.5 (3)C38—C33—C34—C351.0 (2)
C2—C3—C4—C50.2 (3)P1—C33—C34—C35−174.42 (13)
C3—C4—C5—C61.0 (3)C33—C34—C35—C360.0 (3)
C2—C1—C6—N2−178.41 (13)C34—C35—C36—C37−0.8 (3)
C7—C1—C6—N21.8 (2)C35—C36—C37—C380.6 (3)
C2—C1—C6—C51.6 (2)C36—C37—C38—C330.4 (3)
C7—C1—C6—C5−178.21 (14)C34—C33—C38—C37−1.2 (2)
C4—C5—C6—N2178.11 (15)P1—C33—C38—C37174.44 (13)
C4—C5—C6—C1−1.9 (2)N2—C8—N1—C7−2.4 (2)
C6—C1—C7—O1176.98 (14)N3—C8—N1—C7178.00 (12)
C2—C1—C7—O1−2.8 (2)N2—C8—N1—C15175.68 (13)
C6—C1—C7—N1−4.37 (18)N3—C8—N1—C15−3.87 (18)
C2—C1—C7—N1175.84 (12)O1—C7—N1—C8−176.54 (12)
C14—C9—C10—C111.7 (3)C1—C7—N1—C84.71 (18)
N3—C9—C10—C11−179.32 (15)O1—C7—N1—C155.26 (19)
C9—C10—C11—C120.2 (3)C1—C7—N1—C15−173.48 (11)
C10—C11—C12—C13−1.8 (3)C20—C15—N1—C8−77.32 (17)
C11—C12—C13—C141.7 (3)C16—C15—N1—C8102.31 (15)
C12—C13—C14—C90.1 (3)C20—C15—N1—C7100.87 (15)
C10—C9—C14—C13−1.8 (2)C16—C15—N1—C7−79.50 (16)
N3—C9—C14—C13179.28 (15)N3—C8—N2—C6179.02 (13)
C20—C15—C16—O2−177.73 (14)N1—C8—N2—C6−0.5 (2)
N1—C15—C16—O22.6 (2)C1—C6—N2—C80.8 (2)
C20—C15—C16—C171.5 (2)C5—C6—N2—C8−179.21 (14)
N1—C15—C16—C17−178.15 (13)N2—C8—N3—C9−0.7 (2)
O2—C16—C17—C18179.01 (14)N1—C8—N3—C9178.85 (14)
C15—C16—C17—C18−0.3 (2)C10—C9—N3—C8166.44 (15)
C16—C17—C18—C19−0.6 (3)C14—C9—N3—C8−14.6 (3)
C17—C18—C19—C200.2 (3)C28—C27—P1—O3−31.45 (13)
C18—C19—C20—C151.1 (3)C32—C27—P1—O3151.32 (12)
C16—C15—C20—C19−1.9 (2)C28—C27—P1—C2191.57 (12)
N1—C15—C20—C19177.73 (14)C32—C27—P1—C21−85.66 (14)
C26—C21—C22—C231.1 (2)C28—C27—P1—C33−153.95 (11)
P1—C21—C22—C23−176.91 (12)C32—C27—P1—C3328.83 (15)
C21—C22—C23—C240.8 (3)C22—C21—P1—O3−18.40 (14)
C22—C23—C24—C25−1.9 (3)C26—C21—P1—O3163.67 (11)
C23—C24—C25—C261.0 (3)C22—C21—P1—C27−140.85 (12)
C24—C25—C26—C210.9 (3)C26—C21—P1—C2741.22 (14)
C22—C21—C26—C25−2.0 (2)C22—C21—P1—C33103.34 (12)
P1—C21—C26—C25175.96 (12)C26—C21—P1—C33−74.59 (13)
C32—C27—C28—C290.2 (2)C38—C33—P1—O3−35.40 (14)
P1—C27—C28—C29−177.17 (12)C34—C33—P1—O3139.99 (12)
C27—C28—C29—C300.8 (2)C38—C33—P1—C2787.37 (13)
C28—C29—C30—C31−0.9 (3)C34—C33—P1—C27−97.24 (13)
C29—C30—C31—C320.0 (3)C38—C33—P1—C21−158.00 (12)
C30—C31—C32—C271.0 (3)C34—C33—P1—C2117.38 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2A···O3i0.815 (18)1.862 (19)2.6436 (15)160.1 (18)

Symmetry codes: (i) x, −y+3/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5345).

References

  • Bruker (2000). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2001). SADABS University of Goöttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Yang, X. H., Wu, M. H., Sun, S. F., Ding, M. W., Xie, J. L. & Xia, Q. H. (2008). J. Heterocycl. Chem.45, 1365–1369.

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