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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3207–o3208.
Published online 2010 November 17. doi:  10.1107/S1600536810046659
PMCID: PMC3011645

Ethyl 1-benzyl-5-{[(isopropyl­amino)(3-nitro­phen­oxy)methyl­idene]amino}-1H-1,2,3-triazole-4-carboxyl­ate

Abstract

In the title compound, C22H24N6O5, the triazole ring is essentially planar with a maximum deviation of 0.005 (2) Å and forms dihedral angles of 79.78 (11) and 86.22 (11)° with the phenyl and benzene rings, respectively. In the crystal, mol­ecules are linked by inter­molecular N—H(...)N, C—H(...)O and C—H(...)π inter­actions into a three-dimensional network.

Related literature

For the biological activity of 8-aza­guanine derivatives, see: Roblin et al. (1945 [triangle]); Ding et al. (2004 [triangle]); Mitchell et al. (1950 [triangle]); Levine et al. (1963 [triangle]); Montgomery et al. (1962 [triangle]); Yamamoto et al. (1967 [triangle]); Bariana (1971 [triangle]); Holland et al. (1975 [triangle]). For related structures, see: Chen & Shi (2006 [triangle]); Ferguson et al. (1998 [triangle]); Li et al. (2004 [triangle]); Maldonado et al. (2006 [triangle]); Wang et al. (2006 [triangle]); Xiao & Shi (2007 [triangle]); Zeng et al. (2006 [triangle], 2009 [triangle]); Zhao, Hu et al. (2005 [triangle]); Zhao, Wang & Ding (2005 [triangle]); Zhao, Xie et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3207-scheme1.jpg

Experimental

Crystal data

  • C22H24N6O5
  • M r = 452.47
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3207-efi1.jpg
  • a = 11.5019 (7) Å
  • b = 14.5616 (9) Å
  • c = 14.1758 (9) Å
  • β = 106.384 (1)°
  • V = 2277.8 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 298 K
  • 0.16 × 0.12 × 0.10 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.985, T max = 0.990
  • 16973 measured reflections
  • 5620 independent reflections
  • 4276 reflections with I > 2σ(I)
  • R int = 0.069

Refinement

  • R[F 2 > 2σ(F 2)] = 0.067
  • wR(F 2) = 0.170
  • S = 1.11
  • 5620 reflections
  • 304 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [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: 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 global, I. DOI: 10.1107/S1600536810046659/rz2518sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046659/rz2518Isup2.hkl

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

Acknowledgments

We gratefully acknowledge financial support of this work by the National Basic Research Program of China (2003CB114400), the National Natural Science Foundation of China (20372023, 20102001), the Educational Commission of Hubei Province of China (grant No. B200624004, B20092412) and the Shiyan Municipal Science and Technology Bureau (grant No. 20061835).

supplementary crystallographic information

Comment

The derivatives of heterocycles containing 8-azaguanine system, which are well known bioisosteres of guanine, are of great importance because of their remarkable biological properties. Some of these activities include antimicrobial or antifungal activities (Roblin et al., 1945; Ding et al., 2004), encephaloma cell inhibitor activity (Mitchell et al., 1950; Levine et al., 1963), antileukemie activity (Montgomery et al., 1962), hypersusceptibility inhibitor activity and acesodyne activity (Yamamoto et al., 1967; Bariana, 1971; Holland et al., 1975). In recent years, our group has been engaged in the preparation of derivatives of 8-azaguanine via aza-Wittig reaction of beta-ethoxycarbonyl iminophosphorane with aromatic isocyanate (Zhao, Xie et al., 2005). As a continuation of our research for new biologically active heterocycles, the title compound was obtained as an intermediate product from β-ethoxycarbonyl iminophosphorane with an alphalic isocyanate, and structurally characterized in this context.

In the title compound (Fig. 1), bond lengths and angles within the triazole ring are in good agreement with those observed for closely related structures (Zhao, Hu et al., 2005; Zhao, Wang & Ding, 2005). As reported for related compounds (Ferguson et al., 1998; Li et al., 2004; Maldonado et al., 2006; Zeng et al., 2006, 2009; Wang et al., 2006; Xiao & Shi, 2007; Chen & Shi, 2006), the triazole ring system is essentially planar, with a maximum displacement of 0.005 (2) Å for atom N3, and forms dihedral angles of 79.78 (11) and 86.22 (11)° with the phenyl and benzene rings, respectively. In the crystal packing, molecules are linked by intermolecular N—H···N, C—H···O and C—H···π hydrogen bonding interactions (Table 1) in a three-dimensional network.

Experimental

To a solution of carbodiimide prepared according to Wang et al. (2006) in a mixed solvent (CH2Cl2/CH3CN, 1:4 v/v, 15 ml) was added 3-nitrobenzene (3 mmol), and the reaction mixture was stirred for 6 h. The solvent was removed under reduced pressure and the residue was recrystallized from EtOH to give the title compound in 92% yield (m.p. 437 K). Elemental analysis: calculated for C22H24N6O5: C, 58.40; H, 5.35; N, 18.57%. Found: C, 58.08; H, 5.49; N, 18.29%. Crystals suitable for X-ray diffraction study were obtained by recrystallization from EtOH and dichloromethane (1:3 v/v) at room temperature.

Refinement

The H atom attached to atom N5 was located in a difference Fourier map and allowed to ride on their parent atom with a restraint of N—H = 0.83 Å and Uiso(H) = 1.2Ueq(N). Other H atoms were placed at calculated positions and treated as riding atoms, with C—H = 0.93–0.97 Å, and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl H atoms.

Figures

Fig. 1.
View of the molecule of showing the atom-labeling scheme. Displacement ellipsoids are drawn at 50% probability level. H-atoms are represented by circles of arbitrary size.

Crystal data

C22H24N6O5F(000) = 952
Mr = 452.47Dx = 1.319 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4925 reflections
a = 11.5019 (7) Åθ = 2.3–27.5°
b = 14.5616 (9) ŵ = 0.10 mm1
c = 14.1758 (9) ÅT = 298 K
β = 106.384 (1)°Block, colourless
V = 2277.8 (2) Å30.16 × 0.12 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer5620 independent reflections
Radiation source: fine-focus sealed tube4276 reflections with I > 2σ(I)
graphiteRint = 0.069
[var phi] and ω scansθmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −15→15
Tmin = 0.985, Tmax = 0.990k = −19→11
16973 measured reflectionsl = −18→18

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)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170H atoms treated by a mixture of independent and constrained refinement
S = 1.11w = 1/[σ2(Fo2) + (0.0702P)2 + 0.3769P] where P = (Fo2 + 2Fc2)/3
5620 reflections(Δ/σ)max = 0.001
304 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = −0.19 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
C10.83494 (16)0.73129 (13)0.46761 (13)0.0443 (4)
C20.92546 (19)0.79033 (16)0.45953 (18)0.0607 (6)
H20.90530.84480.42450.073*
C31.0448 (2)0.7693 (2)0.5027 (2)0.0778 (8)
H31.10510.80960.49690.093*
C41.0756 (2)0.6893 (3)0.5545 (2)0.0880 (10)
H41.15650.67610.58550.106*
C50.9865 (3)0.6285 (2)0.56061 (19)0.0858 (9)
H51.00730.57310.59360.103*
C60.8662 (2)0.64966 (17)0.51778 (17)0.0634 (6)
H60.80610.60880.52270.076*
C70.70362 (17)0.75548 (14)0.42216 (15)0.0496 (5)
H7A0.68920.76430.35200.060*
H7B0.65310.70500.43180.060*
C80.67486 (14)0.92697 (13)0.43699 (12)0.0386 (4)
C90.64906 (14)0.97754 (13)0.51172 (12)0.0374 (4)
C100.65826 (15)1.07626 (14)0.52721 (13)0.0428 (4)
C110.6438 (2)1.19830 (17)0.63312 (18)0.0666 (6)
H11A0.58761.23470.58320.080*
H11B0.72561.21780.63690.080*
C120.6194 (3)1.2108 (2)0.7301 (2)0.0843 (8)
H12A0.53981.18840.72640.126*
H12B0.62441.27490.74680.126*
H12C0.67841.17730.77950.126*
C130.65271 (15)1.00782 (13)0.29254 (12)0.0405 (4)
C140.48968 (17)1.11872 (14)0.21120 (13)0.0473 (5)
H140.52741.11870.15720.057*
C150.35540 (19)1.09763 (18)0.16922 (17)0.0655 (6)
H15A0.34571.03710.14130.098*
H15B0.31941.14170.11910.098*
H15C0.31641.10080.22070.098*
C160.5115 (3)1.21091 (17)0.26153 (18)0.0714 (7)
H16A0.47591.21160.31520.107*
H16B0.47541.25820.21530.107*
H16C0.59711.22160.28610.107*
C170.82682 (16)1.01845 (14)0.23484 (13)0.0435 (4)
C180.85824 (16)0.97580 (13)0.15946 (13)0.0432 (4)
H180.79970.95530.10380.052*
C190.98042 (18)0.96439 (14)0.16946 (15)0.0496 (5)
C201.06905 (19)0.99366 (19)0.25005 (19)0.0682 (7)
H201.15050.98450.25490.082*
C211.0339 (2)1.0371 (2)0.32389 (19)0.0785 (8)
H211.09261.05800.37920.094*
C220.9133 (2)1.04989 (19)0.31693 (16)0.0652 (6)
H220.89031.07940.36700.078*
N10.66986 (13)0.83894 (11)0.46539 (11)0.0430 (4)
N20.64102 (15)0.83418 (12)0.55231 (12)0.0498 (4)
N30.62788 (13)0.91804 (12)0.57907 (11)0.0447 (4)
N40.70987 (13)0.94745 (12)0.35461 (11)0.0455 (4)
N50.54469 (13)1.04458 (12)0.28047 (11)0.0439 (4)
H5A0.5090 (19)1.0317 (14)0.3220 (16)0.053*
N61.0155 (2)0.91968 (15)0.08856 (18)0.0698 (6)
O10.69213 (14)1.12893 (11)0.47476 (11)0.0593 (4)
O20.62878 (12)1.10169 (9)0.60849 (10)0.0500 (3)
O30.70407 (11)1.03569 (10)0.22136 (9)0.0528 (4)
O40.9375 (2)0.89508 (16)0.01765 (16)0.1013 (7)
O51.1227 (2)0.91031 (17)0.09688 (19)0.1151 (8)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0471 (10)0.0477 (11)0.0431 (9)0.0052 (8)0.0210 (8)−0.0076 (8)
C20.0551 (12)0.0505 (13)0.0834 (15)0.0011 (10)0.0306 (11)−0.0126 (11)
C30.0489 (12)0.0810 (19)0.108 (2)−0.0053 (12)0.0295 (13)−0.0411 (17)
C40.0548 (14)0.125 (3)0.0771 (17)0.0327 (17)0.0069 (12)−0.0258 (18)
C50.088 (2)0.101 (2)0.0679 (16)0.0427 (18)0.0212 (14)0.0184 (15)
C60.0686 (14)0.0688 (16)0.0606 (13)0.0095 (12)0.0308 (11)0.0101 (11)
C70.0496 (10)0.0482 (12)0.0541 (11)0.0008 (9)0.0196 (9)−0.0052 (9)
C80.0280 (7)0.0500 (11)0.0404 (9)0.0051 (7)0.0140 (6)0.0050 (8)
C90.0305 (7)0.0485 (11)0.0368 (8)−0.0005 (7)0.0152 (6)0.0024 (8)
C100.0324 (8)0.0556 (12)0.0417 (9)−0.0059 (8)0.0126 (7)−0.0004 (9)
C110.0732 (15)0.0536 (14)0.0767 (15)−0.0157 (11)0.0271 (12)−0.0179 (12)
C120.098 (2)0.0805 (19)0.0757 (17)0.0005 (15)0.0265 (14)−0.0294 (15)
C130.0398 (9)0.0514 (11)0.0351 (8)0.0012 (8)0.0184 (7)0.0005 (8)
C140.0497 (10)0.0560 (12)0.0424 (9)0.0108 (9)0.0232 (8)0.0099 (9)
C150.0512 (12)0.0804 (17)0.0640 (13)0.0159 (11)0.0150 (10)0.0107 (12)
C160.0987 (18)0.0556 (14)0.0640 (14)0.0020 (13)0.0295 (13)0.0087 (12)
C170.0412 (9)0.0518 (11)0.0438 (9)0.0010 (8)0.0222 (7)0.0068 (8)
C180.0454 (9)0.0456 (11)0.0429 (9)−0.0027 (8)0.0197 (8)0.0027 (8)
C190.0514 (11)0.0474 (12)0.0607 (12)0.0034 (9)0.0334 (9)0.0061 (9)
C200.0402 (10)0.0885 (18)0.0812 (16)−0.0018 (11)0.0255 (11)0.0057 (14)
C210.0529 (13)0.112 (2)0.0677 (15)−0.0206 (13)0.0130 (11)−0.0204 (15)
C220.0605 (13)0.0871 (18)0.0546 (12)−0.0113 (12)0.0270 (10)−0.0182 (12)
N10.0407 (8)0.0483 (10)0.0453 (8)0.0047 (7)0.0209 (6)0.0040 (7)
N20.0539 (9)0.0551 (11)0.0489 (9)0.0017 (8)0.0280 (7)0.0075 (8)
N30.0471 (8)0.0511 (10)0.0423 (8)0.0000 (7)0.0228 (7)0.0038 (7)
N40.0443 (8)0.0578 (10)0.0419 (8)0.0127 (7)0.0242 (6)0.0081 (7)
N50.0410 (8)0.0572 (10)0.0401 (8)0.0081 (7)0.0224 (6)0.0109 (7)
N60.0799 (14)0.0630 (13)0.0853 (15)0.0147 (11)0.0538 (12)0.0007 (11)
O10.0667 (9)0.0590 (9)0.0594 (8)−0.0195 (7)0.0296 (7)0.0017 (7)
O20.0562 (8)0.0491 (8)0.0505 (7)−0.0073 (6)0.0244 (6)−0.0071 (6)
O30.0456 (7)0.0770 (10)0.0447 (7)0.0127 (7)0.0271 (6)0.0163 (7)
O40.1143 (17)0.1171 (18)0.0855 (13)0.0095 (13)0.0492 (13)−0.0371 (13)
O50.0924 (14)0.129 (2)0.156 (2)0.0250 (13)0.0866 (15)−0.0155 (16)

Geometric parameters (Å, °)

C1—C21.380 (3)C13—N51.319 (2)
C1—C61.380 (3)C13—O31.367 (2)
C1—C71.507 (3)C14—N51.476 (2)
C2—C31.371 (3)C14—C161.508 (3)
C2—H20.9300C14—C151.522 (3)
C3—C41.370 (4)C14—H140.9800
C3—H30.9300C15—H15A0.9600
C4—C51.375 (5)C15—H15B0.9600
C4—H40.9300C15—H15C0.9600
C5—C61.379 (4)C16—H16A0.9600
C5—H50.9300C16—H16B0.9600
C6—H60.9300C16—H16C0.9600
C7—N11.462 (2)C17—C181.370 (3)
C7—H7A0.9700C17—C221.378 (3)
C7—H7B0.9700C17—O31.393 (2)
C8—N11.350 (2)C18—C191.382 (3)
C8—N41.371 (2)C18—H180.9300
C8—C91.389 (2)C19—C201.367 (3)
C9—N31.361 (2)C19—N61.471 (3)
C9—C101.454 (3)C20—C211.377 (3)
C10—O11.207 (2)C20—H200.9300
C10—O21.342 (2)C21—C221.376 (3)
C11—O21.448 (3)C21—H210.9300
C11—C121.489 (3)C22—H220.9300
C11—H11A0.9700N1—N21.365 (2)
C11—H11B0.9700N2—N31.300 (2)
C12—H12A0.9600N5—H5A0.83 (2)
C12—H12B0.9600N6—O41.198 (3)
C12—H12C0.9600N6—O51.212 (3)
C13—N41.286 (2)
C2—C1—C6119.1 (2)N5—C14—C15108.05 (16)
C2—C1—C7120.50 (19)C16—C14—C15112.33 (19)
C6—C1—C7120.38 (19)N5—C14—H14108.6
C3—C2—C1120.5 (2)C16—C14—H14108.6
C3—C2—H2119.7C15—C14—H14108.6
C1—C2—H2119.7C14—C15—H15A109.5
C4—C3—C2120.3 (3)C14—C15—H15B109.5
C4—C3—H3119.9H15A—C15—H15B109.5
C2—C3—H3119.9C14—C15—H15C109.5
C3—C4—C5119.8 (2)H15A—C15—H15C109.5
C3—C4—H4120.1H15B—C15—H15C109.5
C5—C4—H4120.1C14—C16—H16A109.5
C4—C5—C6120.1 (3)C14—C16—H16B109.5
C4—C5—H5120.0H16A—C16—H16B109.5
C6—C5—H5120.0C14—C16—H16C109.5
C5—C6—C1120.2 (2)H16A—C16—H16C109.5
C5—C6—H6119.9H16B—C16—H16C109.5
C1—C6—H6119.9C18—C17—C22121.54 (18)
N1—C7—C1111.57 (16)C18—C17—O3117.06 (16)
N1—C7—H7A109.3C22—C17—O3121.18 (17)
C1—C7—H7A109.3C17—C18—C19117.32 (18)
N1—C7—H7B109.3C17—C18—H18121.3
C1—C7—H7B109.3C19—C18—H18121.3
H7A—C7—H7B108.0C20—C19—C18123.04 (19)
N1—C8—N4120.53 (16)C20—C19—N6119.04 (19)
N1—C8—C9103.88 (14)C18—C19—N6117.92 (19)
N4—C8—C9135.35 (18)C19—C20—C21117.96 (19)
N3—C9—C8108.45 (16)C19—C20—H20121.0
N3—C9—C10122.91 (15)C21—C20—H20121.0
C8—C9—C10128.12 (16)C22—C21—C20120.9 (2)
O1—C10—O2123.88 (19)C22—C21—H21119.5
O1—C10—C9123.91 (17)C20—C21—H21119.5
O2—C10—C9112.17 (15)C21—C22—C17119.2 (2)
O2—C11—C12107.5 (2)C21—C22—H22120.4
O2—C11—H11A110.2C17—C22—H22120.4
C12—C11—H11A110.2C8—N1—N2111.03 (15)
O2—C11—H11B110.2C8—N1—C7128.74 (15)
C12—C11—H11B110.2N2—N1—C7119.81 (16)
H11A—C11—H11B108.5N3—N2—N1107.07 (15)
C11—C12—H12A109.5N2—N3—C9109.55 (14)
C11—C12—H12B109.5C13—N4—C8121.01 (14)
H12A—C12—H12B109.5C13—N5—C14126.48 (15)
C11—C12—H12C109.5C13—N5—H5A117.0 (15)
H12A—C12—H12C109.5C14—N5—H5A115.6 (15)
H12B—C12—H12C109.5O4—N6—O5123.3 (2)
N4—C13—N5130.36 (16)O4—N6—C19118.8 (2)
N4—C13—O3117.65 (15)O5—N6—C19118.0 (2)
N5—C13—O3111.79 (15)C10—O2—C11115.68 (16)
N5—C14—C16110.70 (16)C13—O3—C17118.53 (14)
C6—C1—C2—C3−1.6 (3)C9—C8—N1—N20.76 (18)
C7—C1—C2—C3178.52 (19)N4—C8—N1—C73.4 (3)
C1—C2—C3—C40.0 (4)C9—C8—N1—C7−171.70 (16)
C2—C3—C4—C52.0 (4)C1—C7—N1—C889.8 (2)
C3—C4—C5—C6−2.4 (4)C1—C7—N1—N2−82.1 (2)
C4—C5—C6—C10.8 (4)C8—N1—N2—N3−0.05 (19)
C2—C1—C6—C51.1 (3)C7—N1—N2—N3173.18 (15)
C7—C1—C6—C5−179.0 (2)N1—N2—N3—C9−0.72 (19)
C2—C1—C7—N1−62.2 (2)C8—C9—N3—N21.21 (19)
C6—C1—C7—N1117.9 (2)C10—C9—N3—N2−171.13 (16)
N1—C8—C9—N3−1.17 (17)N5—C13—N4—C8−16.3 (3)
N4—C8—C9—N3−175.21 (18)O3—C13—N4—C8169.37 (17)
N1—C8—C9—C10170.66 (17)N1—C8—N4—C13136.47 (19)
N4—C8—C9—C10−3.4 (3)C9—C8—N4—C13−50.3 (3)
N3—C9—C10—O1170.10 (17)N4—C13—N5—C14175.4 (2)
C8—C9—C10—O1−0.7 (3)O3—C13—N5—C14−10.0 (3)
N3—C9—C10—O2−7.7 (2)C16—C14—N5—C13−94.9 (2)
C8—C9—C10—O2−178.49 (15)C15—C14—N5—C13141.7 (2)
C22—C17—C18—C190.8 (3)C20—C19—N6—O4−179.2 (2)
O3—C17—C18—C19175.51 (16)C18—C19—N6—O40.0 (3)
C17—C18—C19—C20−0.1 (3)C20—C19—N6—O50.2 (3)
C17—C18—C19—N6−179.29 (18)C18—C19—N6—O5179.4 (2)
C18—C19—C20—C21−0.5 (4)O1—C10—O2—C11−2.0 (3)
N6—C19—C20—C21178.6 (2)C9—C10—O2—C11175.81 (16)
C19—C20—C21—C220.5 (4)C12—C11—O2—C10−174.08 (18)
C20—C21—C22—C170.2 (4)N4—C13—O3—C17−17.6 (3)
C18—C17—C22—C21−0.8 (4)N5—C13—O3—C17166.98 (17)
O3—C17—C22—C21−175.3 (2)C18—C17—O3—C13128.60 (19)
N4—C8—N1—N2175.89 (14)C22—C17—O3—C13−56.7 (3)

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the triazole and C1–C6 phenyl rings, respectively.
D—H···AD—HH···AD···AD—H···A
N5—H5A···N3i0.83 (2)2.50 (2)3.230 (2)148 (2)
C3—H3···O1ii0.932.423.303 (3)158
C21—H21···Cg1ii0.932.983.829 (3)153
C14—H14···Cg2iii0.982.783.625 (2)145

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+2, −y+2, −z+1; (iii) −x+3/2, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2518).

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