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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2384.
Published online 2010 August 25. doi:  10.1107/S1600536810032654
PMCID: PMC3007932

Ethyl 2-isopropyl­amino-6-methyl-8-oxo-3-phenyl-3H,8H-furo[2,3-d][1,2,4]triazolo[1,5-a]pyrimidine-7-carboxyl­ate

Abstract

In the title compound, C20H21N5O4, the ring system containing the three fused rings is essentially planar (r.m.s. deviation for all 12 non-H atoms = 0.041 Å). The phenyl ring makes a dihedral angle of 54.41 (6)° with this ring system. The isopropyl group is disordered over two positions, with site-occupancy factors of 0.753 (9) and 0.247 (9). The structure is mainly stabilized by weak inter­molecular N—H(...)O and intra­molecular C—H(...)O hydrogen-bonding inter­actions and π–π inter­actions, with inter­planar distances of 3.415 (1) Å between adjacent furan ring centroids and 3.420 (1) Å between the benzene and pyrimidinone rings.

Related literature

For the crystal structures of other fused pyrimidinone derivatives and related literature, see: Ding et al. (2004 [triangle]); Hu et al. (2005 [triangle], 2006 [triangle], 2007 [triangle], 2008 [triangle]).

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Object name is e-66-o2384-scheme1.jpg

Experimental

Crystal data

  • C20H21N5O4
  • M r = 395.42
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2384-efi1.jpg
  • a = 19.9810 (11) Å
  • b = 37.3673 (19) Å
  • c = 10.7181 (6) Å
  • V = 8002.5 (7) Å3
  • Z = 16
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 295 K
  • 0.20 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART 4K CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003 [triangle]) T min = 0.981, T max = 0.991
  • 21970 measured reflections
  • 2074 independent reflections
  • 1883 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.109
  • S = 1.09
  • 2074 reflections
  • 290 parameters
  • 5 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.14 e Å−3
  • Δρmin = −0.11 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810032654/bt5323sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032654/bt5323Isup2.hkl

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

Acknowledgments

The authors are grateful to Dr Y. G. Hu (Institute of Medicinal Chemistry, Hubei Medical University, Shiyan, China) for help with synthesis and analysis. This work was supported by the Education Commission of Hubei Province of China (grant No. B20102107) and Shiyan Municipal Science and Technology Bureau (grant No. 2010-037s).

supplementary crystallographic information

Comment

Fused pyrimidine compounds are valued not only for their rich and varied chemistry, but also for many important biological properties. On the other hand, heterocycles containing triazoles nucleus also exhibit various biological activities.

The introduction of an triazole ring to the furopyrimidine system is expected to influence the biological activities significantly. As a part of our ongoing investigations on the preparation of derivatives of heterocyclic compounds (Ding et al., (2004), Hu et al., 2005, 2006, 2007, 2008), we have synthesized and structurally characterized characterized the title compound, and here we wish to report an X-ray crystal structure of it(Fig. 1).

In the molecule, the bond lengths and angles are unexceptional. In the title compound the ring system containing the three fused rings is essentially planar (r.m.s. deviation for all 12 non-H atoms 0.041 Å). The phenyl ring makes a dihedral angles of 54.41 (06)° with this ring system. The isopropyl group in molecule is disordered over two positions, with site occupancy factors 0.753 (9) and 0.247 (9); The structure is mainly stabilized by intermolecular weak N—H···O and intramolecular C—H···O hydrogen bonding interactions (Table 1) and π-π interactions with interplanar distances of 3.537Å between adjacent furan ring centroids (symmetry code: -x, -y, z) and 3.681Å between phenyl and pyrimidinone rings (symmetry code: 1/4 + x,1/4 - y,1/4 + z).

Experimental

The title compound was obtained in excellent yield via aza-Wittig reaction. Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from a mixed solvent of ethanol and dichloromethane (1:2 v/v) at room temperature.

Refinement

In the absence of anomalous scatterers, 2307 Friedel pairs were merged. 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, C—H = 0.98 Å, Uiso = 1.2Ueq (C) for CH, C—H = 0.97 Å, Uiso = 1.2Ueq (C) for CH2, C—H = 0.96 Å, Uiso = 1.5Ueq (C) for CH3. The coordinates of the H atom bonded to N were refined with Uiso = 1.2Ueq(N) and the N—H distance restrained to 0.86 (1) Å. The bond distances and 1–3 distances in the disordered groups were restrained to be equal within an effective e.s.d. of 0.01 Å.

Figures

Fig. 1.
The molecular structure of the title compound, showing the atom-labeling scheme.

Crystal data

C20H21N5O4F(000) = 3328
Mr = 395.42Dx = 1.313 Mg m3
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2dCell parameters from 3861 reflections
a = 19.9810 (11) Åθ = 2.2–20.8°
b = 37.3673 (19) ŵ = 0.09 mm1
c = 10.7181 (6) ÅT = 295 K
V = 8002.5 (7) Å3Block, purple
Z = 160.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer2074 independent reflections
Radiation source: fine-focus sealed tube1883 reflections with I > 2σ(I)
graphiteRint = 0.042
[var phi] and ω scansθmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)h = −25→24
Tmin = 0.981, Tmax = 0.991k = −44→47
21970 measured reflectionsl = −13→13

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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 1.09w = 1/[σ2(Fo2) + (0.0601P)2 + 2.4148P] where P = (Fo2 + 2Fc2)/3
2074 reflections(Δ/σ)max < 0.001
290 parametersΔρmax = 0.14 e Å3
5 restraintsΔρmin = −0.11 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*/UeqOcc. (<1)
C10.25088 (16)0.07862 (8)0.2745 (4)0.0618 (8)
H10.26340.06940.19740.074*
C20.29491 (17)0.07774 (9)0.3748 (4)0.0743 (11)
H20.33780.06850.36400.089*
C30.2759 (2)0.09026 (10)0.4890 (4)0.0829 (12)
H30.30520.08890.55620.099*
C40.2140 (2)0.10476 (12)0.5044 (4)0.0831 (11)
H40.20110.11330.58220.100*
C50.17048 (18)0.10680 (10)0.4059 (3)0.0678 (9)
H50.12870.11730.41670.081*
C60.18834 (15)0.09340 (8)0.2912 (3)0.0520 (7)
C70.07894 (14)0.07677 (7)0.1978 (3)0.0487 (6)
C80.14928 (15)0.10258 (7)0.0675 (3)0.0517 (7)
C90.21415 (19)0.12881 (12)−0.1012 (4)0.0790 (11)
H9A0.19730.1093−0.15370.095*0.76
H9B0.17200.1295−0.14790.095*0.24
C100.1741 (3)0.16260 (18)−0.1310 (7)0.107 (2)0.76
H10A0.12760.1584−0.11490.160*0.76
H10B0.18010.1687−0.21730.160*0.76
H10C0.18960.1819−0.07960.160*0.76
C110.2851 (3)0.1340 (3)−0.1290 (7)0.137 (3)0.76
H11A0.30320.1519−0.07450.205*0.76
H11B0.29010.1416−0.21410.205*0.76
H11C0.30860.1118−0.11680.205*0.76
C11'0.2599 (11)0.1007 (4)−0.153 (2)0.125 (8)0.24
H11D0.29960.0995−0.10230.188*0.24
H11E0.27180.1067−0.23670.188*0.24
H11F0.23760.0780−0.15140.188*0.24
C10'0.2513 (12)0.1649 (3)−0.110 (3)0.187 (17)0.24
H10D0.22120.1840−0.08810.281*0.24
H10E0.26740.1684−0.19320.281*0.24
H10F0.28850.1649−0.05280.281*0.24
C12−0.00778 (15)0.06210 (8)0.0432 (3)0.0575 (8)
C13−0.03791 (14)0.04496 (8)0.1483 (3)0.0592 (8)
C14−0.00908 (14)0.04888 (8)0.2641 (3)0.0549 (7)
C15−0.09993 (16)0.02527 (8)0.1723 (4)0.0680 (10)
C16−0.10362 (17)0.02052 (9)0.2962 (4)0.0715 (10)
C17−0.1520 (2)0.00305 (13)0.3833 (5)0.0982 (14)
H17A−0.1864−0.00870.33600.147*
H17B−0.17190.02090.43610.147*
H17C−0.1289−0.01420.43360.147*
C18−0.1456 (2)0.00781 (11)0.0816 (5)0.0832 (12)
C19−0.1552 (3)−0.01350 (12)−0.1254 (6)0.1117 (18)
H19A−0.19460.0006−0.14520.134*
H19B−0.1697−0.0370−0.09760.134*
C20−0.1128 (4)−0.0169 (2)−0.2349 (7)0.158 (3)
H20A−0.09850.0064−0.26140.237*
H20B−0.1375−0.0282−0.30090.237*
H20C−0.0743−0.0312−0.21470.237*
N10.14054 (11)0.09293 (6)0.1915 (2)0.0506 (6)
N20.05524 (11)0.07635 (6)0.0793 (2)0.0511 (6)
N30.09879 (12)0.09351 (6)−0.0029 (2)0.0538 (6)
N40.20563 (14)0.11862 (8)0.0286 (3)0.0636 (7)
H4A0.2249 (17)0.1327 (8)0.081 (3)0.076*
N50.04897 (13)0.06436 (7)0.2978 (2)0.0568 (6)
O1−0.02832 (11)0.06660 (6)−0.0623 (2)0.0728 (7)
O2−0.04849 (11)0.03475 (6)0.3546 (2)0.0695 (6)
O3−0.20042 (15)−0.00291 (9)0.1061 (4)0.1254 (13)
O4−0.11678 (14)0.00387 (7)−0.0285 (3)0.0887 (9)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0516 (17)0.0511 (16)0.083 (2)−0.0037 (13)−0.0061 (16)0.0058 (16)
C20.0521 (19)0.0555 (18)0.115 (3)−0.0055 (15)−0.021 (2)0.016 (2)
C30.088 (3)0.073 (2)0.088 (3)−0.015 (2)−0.043 (2)0.015 (2)
C40.094 (3)0.091 (3)0.065 (2)−0.010 (2)−0.020 (2)0.0011 (19)
C50.063 (2)0.079 (2)0.062 (2)−0.0057 (16)−0.0053 (17)0.0026 (16)
C60.0479 (16)0.0494 (15)0.0587 (17)−0.0094 (13)−0.0064 (13)0.0071 (13)
C70.0428 (15)0.0493 (15)0.0540 (16)−0.0008 (12)−0.0032 (14)−0.0011 (13)
C80.0534 (17)0.0475 (15)0.0542 (17)0.0004 (13)0.0045 (14)−0.0061 (13)
C90.081 (2)0.098 (3)0.0576 (19)−0.019 (2)0.0117 (18)−0.0011 (19)
C100.120 (5)0.113 (5)0.088 (4)−0.002 (4)0.018 (4)0.035 (4)
C110.089 (4)0.226 (10)0.096 (5)−0.018 (6)0.039 (4)0.026 (6)
C11'0.18 (2)0.093 (14)0.105 (15)−0.018 (15)0.062 (16)−0.013 (12)
C10'0.26 (4)0.110 (17)0.19 (3)0.06 (2)0.16 (3)0.081 (19)
C120.0508 (17)0.0457 (16)0.076 (2)0.0031 (13)−0.0168 (16)−0.0029 (15)
C130.0449 (17)0.0515 (17)0.081 (2)−0.0002 (13)−0.0078 (16)−0.0001 (16)
C140.0446 (15)0.0510 (16)0.0692 (19)−0.0032 (13)0.0058 (14)−0.0018 (14)
C150.0450 (18)0.0517 (18)0.107 (3)−0.0007 (14)−0.0087 (18)0.0031 (18)
C160.0485 (18)0.0585 (19)0.108 (3)−0.0056 (14)0.0049 (18)−0.0043 (19)
C170.074 (3)0.091 (3)0.130 (4)−0.023 (2)0.029 (3)−0.012 (3)
C180.058 (2)0.061 (2)0.131 (4)−0.0096 (17)−0.028 (2)0.021 (2)
C190.120 (4)0.063 (2)0.152 (5)−0.015 (2)−0.081 (4)0.011 (3)
C200.194 (7)0.151 (5)0.129 (5)−0.003 (5)−0.057 (5)−0.036 (5)
N10.0410 (12)0.0554 (13)0.0552 (13)−0.0055 (10)−0.0011 (11)0.0000 (11)
N20.0470 (13)0.0505 (13)0.0558 (14)−0.0007 (10)−0.0048 (11)−0.0009 (11)
N30.0586 (15)0.0519 (13)0.0509 (13)−0.0039 (11)−0.0029 (12)−0.0036 (11)
N40.0601 (16)0.0739 (17)0.0566 (16)−0.0145 (14)0.0082 (13)−0.0032 (13)
N50.0484 (14)0.0619 (15)0.0601 (14)−0.0057 (11)0.0008 (12)−0.0012 (12)
O10.0743 (15)0.0658 (13)0.0783 (16)−0.0078 (11)−0.0312 (13)0.0074 (12)
O20.0551 (13)0.0702 (14)0.0832 (15)−0.0106 (11)0.0130 (12)−0.0042 (12)
O30.0740 (18)0.139 (3)0.163 (3)−0.0538 (19)−0.031 (2)0.036 (3)
O40.0692 (16)0.0697 (16)0.127 (3)−0.0056 (13)−0.0370 (18)−0.0125 (16)

Geometric parameters (Å, °)

C1—C61.378 (4)C11'—H11D0.9600
C1—C21.389 (5)C11'—H11E0.9600
C1—H10.9300C11'—H11F0.9600
C2—C31.364 (7)C10'—H10D0.9600
C2—H20.9300C10'—H10E0.9600
C3—C41.361 (6)C10'—H10F0.9600
C3—H30.9300C12—O11.215 (4)
C4—C51.370 (5)C12—N21.421 (4)
C4—H40.9300C12—C131.429 (5)
C5—C61.374 (5)C13—C141.376 (5)
C5—H50.9300C13—C151.464 (5)
C6—N11.434 (4)C14—N51.345 (4)
C7—N51.312 (4)C14—O21.357 (4)
C7—N21.355 (4)C15—C161.342 (6)
C7—N11.373 (3)C15—C181.483 (6)
C8—N31.305 (4)C16—O21.374 (4)
C8—N41.342 (4)C16—C171.494 (6)
C8—N11.387 (4)C17—H17A0.9600
C9—N41.452 (5)C17—H17B0.9600
C9—C111.461 (7)C17—H17C0.9600
C9—C11'1.496 (11)C18—O31.196 (5)
C9—C101.528 (7)C18—O41.321 (6)
C9—C10'1.543 (11)C19—O41.446 (5)
C9—H9A0.9800C19—C201.454 (9)
C9—H9B0.9800C19—H19A0.9700
C10—H9B1.2497C19—H19B0.9700
C10—H10A0.9600C20—H20A0.9600
C10—H10B0.9600C20—H20B0.9600
C10—H10C0.9600C20—H20C0.9600
C11—H11A0.9600N2—N31.394 (3)
C11—H11B0.9600N4—H4A0.86 (3)
C11—H11C0.9600
C6—C1—C2118.9 (3)C9—C10'—H10E109.5
C6—C1—H1120.6H10D—C10'—H10E109.5
C2—C1—H1120.6C9—C10'—H10F109.5
C3—C2—C1120.7 (3)H10D—C10'—H10F109.5
C3—C2—H2119.7H10E—C10'—H10F109.5
C1—C2—H2119.7O1—C12—N2120.1 (3)
C4—C3—C2119.9 (4)O1—C12—C13130.8 (3)
C4—C3—H3120.1N2—C12—C13109.1 (3)
C2—C3—H3120.1C14—C13—C12119.1 (3)
C3—C4—C5120.4 (4)C14—C13—C15104.5 (3)
C3—C4—H4119.8C12—C13—C15136.1 (3)
C5—C4—H4119.8N5—C14—O2118.4 (3)
C4—C5—C6120.3 (4)N5—C14—C13130.4 (3)
C4—C5—H5119.9O2—C14—C13111.1 (3)
C6—C5—H5119.9C16—C15—C13106.7 (3)
C5—C6—C1119.9 (3)C16—C15—C18123.8 (4)
C5—C6—N1119.9 (3)C13—C15—C18128.8 (4)
C1—C6—N1120.1 (3)C15—C16—O2110.9 (3)
N5—C7—N2127.0 (3)C15—C16—C17135.3 (4)
N5—C7—N1127.2 (3)O2—C16—C17113.8 (4)
N2—C7—N1105.8 (2)C16—C17—H17A109.5
N3—C8—N4125.8 (3)C16—C17—H17B109.5
N3—C8—N1112.9 (2)H17A—C17—H17B109.5
N4—C8—N1121.3 (3)C16—C17—H17C109.5
N4—C9—C11110.1 (4)H17A—C17—H17C109.5
N4—C9—C11'103.9 (10)H17B—C17—H17C109.5
N4—C9—C10110.8 (4)O3—C18—O4123.9 (5)
C11—C9—C10110.8 (6)O3—C18—C15124.5 (5)
C11'—C9—C10145.3 (10)O4—C18—C15111.5 (3)
N4—C9—C10'110.0 (11)O4—C19—C20108.0 (5)
C11'—C9—C10'107.3 (9)O4—C19—H19A110.1
N4—C9—H9A108.3C20—C19—H19A110.1
C11—C9—H9A108.3O4—C19—H19B110.1
C10—C9—H9A108.3C20—C19—H19B110.1
C10'—C9—H9A141.5H19A—C19—H19B108.4
N4—C9—H9B113.3C19—C20—H20A109.5
C11—C9—H9B136.6C19—C20—H20B109.5
C11'—C9—H9B110.9H20A—C20—H20B109.5
C10'—C9—H9B111.1C19—C20—H20C109.5
C9—C10—H10A109.5H20A—C20—H20C109.5
C9—C10—H10B109.5H20B—C20—H20C109.5
H9B—C10—H10B95.8C7—N1—C8105.9 (2)
C9—C10—H10C109.5C7—N1—C6124.5 (2)
H9B—C10—H10C147.0C8—N1—C6128.8 (2)
C9—C11—H11A109.5C7—N2—N3111.6 (2)
C9—C11—H11B109.5C7—N2—C12124.7 (3)
C9—C11—H11C109.5N3—N2—C12123.6 (2)
C9—C11'—H11D109.5C8—N3—N2103.7 (2)
C9—C11'—H11E109.5C8—N4—C9120.9 (3)
H11D—C11'—H11E109.5C8—N4—H4A116 (3)
C9—C11'—H11F109.5C9—N4—H4A114 (3)
H11D—C11'—H11F109.5C7—N5—C14109.0 (3)
H11E—C11'—H11F109.5C14—O2—C16106.8 (3)
C9—C10'—H10D109.5C18—O4—C19117.4 (4)
C6—C1—C2—C32.1 (5)N4—C8—N1—C6−8.7 (5)
C1—C2—C3—C4−2.0 (5)C5—C6—N1—C7−56.1 (4)
C2—C3—C4—C50.2 (6)C1—C6—N1—C7120.2 (3)
C3—C4—C5—C61.6 (6)C5—C6—N1—C8135.5 (3)
C4—C5—C6—C1−1.5 (5)C1—C6—N1—C8−48.2 (4)
C4—C5—C6—N1174.8 (3)N5—C7—N2—N3176.9 (3)
C2—C1—C6—C5−0.3 (5)N1—C7—N2—N3−3.0 (3)
C2—C1—C6—N1−176.6 (3)N5—C7—N2—C120.2 (5)
O1—C12—C13—C14−168.6 (3)N1—C7—N2—C12−179.6 (2)
N2—C12—C13—C148.9 (4)O1—C12—N2—C7171.4 (3)
O1—C12—C13—C153.6 (6)C13—C12—N2—C7−6.5 (4)
N2—C12—C13—C15−178.8 (3)O1—C12—N2—N3−4.9 (4)
C12—C13—C14—N5−6.7 (5)C13—C12—N2—N3177.2 (2)
C15—C13—C14—N5178.9 (3)N4—C8—N3—N2177.0 (3)
C12—C13—C14—O2172.3 (3)N1—C8—N3—N2−1.2 (3)
C15—C13—C14—O2−2.2 (3)C7—N2—N3—C82.6 (3)
C14—C13—C15—C162.1 (4)C12—N2—N3—C8179.3 (2)
C12—C13—C15—C16−170.9 (4)N3—C8—N4—C92.3 (5)
C14—C13—C15—C18−168.0 (3)N1—C8—N4—C9−179.6 (3)
C12—C13—C15—C1819.0 (6)C11—C9—N4—C8−160.5 (6)
C13—C15—C16—O2−1.3 (4)C11'—C9—N4—C8−103.2 (11)
C18—C15—C16—O2169.4 (3)C10—C9—N4—C876.5 (5)
C13—C15—C16—C17−179.8 (4)C10'—C9—N4—C8142.2 (10)
C18—C15—C16—C17−9.1 (7)N2—C7—N5—C143.4 (4)
C16—C15—C18—O323.7 (6)N1—C7—N5—C14−176.8 (3)
C13—C15—C18—O3−167.7 (4)O2—C14—N5—C7−179.0 (3)
C16—C15—C18—O4−153.1 (4)C13—C14—N5—C7−0.1 (5)
C13—C15—C18—O415.5 (5)N5—C14—O2—C16−179.5 (3)
N5—C7—N1—C8−177.7 (3)C13—C14—O2—C161.4 (3)
N2—C7—N1—C82.1 (3)C15—C16—O2—C140.0 (4)
N5—C7—N1—C611.6 (5)C17—C16—O2—C14178.9 (3)
N2—C7—N1—C6−168.6 (2)O3—C18—O4—C192.0 (6)
N3—C8—N1—C7−0.5 (3)C15—C18—O4—C19178.8 (3)
N4—C8—N1—C7−178.8 (3)C20—C19—O4—C18−176.6 (4)
N3—C8—N1—C6169.5 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N4—H4A···O1i0.86 (3)2.21 (2)2.978 (4)148 (3)
C17—H17A···O30.962.493.132 (7)124.

Symmetry codes: (i) x+1/4, −y+1/4, z+1/4.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5323).

References

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