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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1505.
Published online 2008 July 16. doi:  10.1107/S160053680802148X
PMCID: PMC2962132

3-(2-Benzamido­phen­yl)-4-(4-hydroxy­phen­yl)-5-methyl-4H-1,2,4-triazol-1-ium chloride

Abstract

In the mol­ecule of the title compound, C22H19N4O2 +·Cl, the 1,2,4-triazole ring is oriented at dihedral angles of 75.57 (14), 53.23 (13) and 68.11 (13)° with respect to the benzamide, aniline and phenol atomatic rings, respectively. An intra­molecular C—H(...)O hydrogen bond results in the formation of a non-planar ten-membered ring. In the crystal structure, inter­molecular O—H(...)Cl and N—H(...)Cl hydrogen bonds link the mol­ecules. There is a C—H(...)π contact between the methyl group and the phenyl ring, and a π–π contact between the hydroxy­phenyl and phenyl rings [centroid–centroid distance = 4.687 (2) Å].

Related literature

For general background, see: Caira et al. (2004 [triangle]); Peeters et al. (1996 [triangle]). For related literature, see: Potts (1961 [triangle]).

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Object name is e-64-o1505-scheme1.jpg

Experimental

Crystal data

  • C22H19N4O2 +·Cl
  • M r = 406.86
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1505-efi1.jpg
  • a = 17.1336 (15) Å
  • b = 9.8967 (9) Å
  • c = 12.1910 (10) Å
  • V = 2067.2 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.21 mm−1
  • T = 296 (2) K
  • 0.25 × 0.20 × 0.18 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.950, T max = 0.960
  • 13329 measured reflections
  • 2809 independent reflections
  • 2480 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.097
  • S = 1.02
  • 2809 reflections
  • 272 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.21 e Å−3
  • Absolute structure: Flack (1983 [triangle]), with 1677 Friedel pairs
  • Flack parameter: 0.06 (7)

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802148X/hk2490sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802148X/hk2490Isup2.hkl

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

Acknowledgments

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, for funding the purchase of the diffractometer at GCU, Lahore.

supplementary crystallographic information

Comment

1,2,4-Triazole is a basic aromatic heterocycle. Its derivatives, such as fluconazole (Caira et al., 2004) and itraconazole (Peeters et al., 1996), find use as antifungals and can be prepared using various routes including Einhorn-Brunner and Pellizzari reactions (Potts, 1961).

In the molecule of the title compound (Fig. 1) the bond lengths and angles are generally within normal ranges. Rings A (C1-C6), B (C8-C13), C (N2-N4/C14/C15) and D (C17-C22) are, of course, planar, and the dihedral angles between them are A/B = 66.39 (14)°, A/C = 75.57 (14)°, A/D = 39.96 (13)°, B/C = 53.23 (13)°, B/D = 78.57 (14)° and C/D = 68.11 (13)°. The intramolecular C-H···O hydrogen bond (Table 1) results in the formation of a non-planar ten-membered ring E (O1/N1/N4/C7/C8/C13/C14/C17/C18/H18).

In the crystal structure, intermolecular O-H···Cl and N-H···Cl hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure. The C—H···π contact (Table 1) between the methyl group and the phenyl ring and π—π contact between the two phenyl rings Cg2···Cg4i [symmetry code: (i) -x, 2 - y, 1/2 + z, where Cg2 and Cg4 are centroids of the rings (C1-C6) and (C17-C22), respectively] further stabilize the structure, with centroid-centroid distance of 4.687 (2) Å.

Experimental

For the preparation of the title compound, N-[2-(hydrazinylcarbonyl)phenyl]- benzamide (0.25 g, 0.98 mmol) and triethyl orthoacetate (1 ml) were refluxed for 2 h. The reaction mixture was cooled to room temperature and 4-aminophenol (0.11 g, 0.98 mmol) was added. Acetic acid (1 ml) was added to the mixture and the contents were refluxed for 1 h. Then, the reaction mixture was added to HCl (8 M) solution. It was crystallized by adding dioxane portion-wise. The crystals were separated by filtration and washed with dioxane (yield; 77%, m.p. 498 K).

Refinement

H atoms, H2A (for OH), H1 and H3A (for NH), were located in difference syntheses and refined [O-H = 0.76 (4) Å, Uiso(H) = 0.0839 Å2 and N-H = 0.81 (3) and 0.97 (3) Å, Uiso(H) = 0.0628 and 0.0492 Å2]. The remaining H atoms were positioned geometrically, with C-H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for aromatic H atoms.

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bond is shown as dotted line.
Fig. 2.
A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Crystal data

C22H19N4O2+·ClF000 = 848
Mr = 406.86Dx = 1.307 Mg m3
Orthorhombic, Pca21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 2009 reflections
a = 17.1336 (15) Åθ = 2.1–28.8º
b = 9.8967 (9) ŵ = 0.21 mm1
c = 12.1910 (10) ÅT = 296 (2) K
V = 2067.2 (3) Å3Prismatic, black
Z = 40.25 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer2809 independent reflections
Radiation source: fine-focus sealed tube2480 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.022
Detector resolution: 7.40 pixels mm-1θmax = 28.8º
T = 296(2) Kθmin = 2.1º
ω scansh = −23→18
Absorption correction: multi-scan(SADABS; Bruker, 2005)k = −13→10
Tmin = 0.950, Tmax = 0.960l = −16→12
13329 measured reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.034  w = 1/[σ2(Fo2) + (0.0606P)2 + 0.2556P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.097(Δ/σ)max = 0.001
S = 1.02Δρmax = 0.20 e Å3
2809 reflectionsΔρmin = −0.21 e Å3
272 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983) with no Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.06 (7)
Secondary atom site location: difference Fourier map

Special details

Geometry. Bond distances, angles etc have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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 > 2sigma(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
Cl0.18901 (3)0.41678 (5)0.23611 (6)0.0441 (2)
O10.08185 (11)0.8416 (2)0.61956 (15)0.0523 (6)
O20.23156 (16)1.1272 (2)0.1626 (2)0.0698 (9)
N1−0.02194 (12)0.7017 (2)0.62595 (16)0.0396 (6)
N20.12701 (11)0.54036 (19)0.55257 (17)0.0394 (5)
N30.20680 (12)0.5419 (2)0.55843 (18)0.0410 (6)
N40.17842 (10)0.69261 (19)0.44104 (16)0.0345 (5)
C10.02424 (13)0.8077 (2)0.79409 (19)0.0364 (6)
C2−0.01415 (15)0.7183 (3)0.8629 (2)0.0451 (8)
C3−0.02023 (18)0.7468 (4)0.9741 (2)0.0583 (10)
C40.0117 (2)0.8628 (3)1.0166 (3)0.0640 (10)
C50.0506 (2)0.9501 (3)0.9485 (3)0.0648 (10)
C60.05751 (18)0.9231 (3)0.8372 (2)0.0513 (8)
C70.03122 (13)0.7860 (2)0.6732 (2)0.0364 (6)
C8−0.03057 (13)0.6865 (2)0.51128 (19)0.0357 (6)
C9−0.10597 (14)0.6966 (3)0.4680 (2)0.0477 (8)
C10−0.11851 (17)0.6838 (3)0.3569 (3)0.0580 (9)
C11−0.05706 (19)0.6642 (3)0.2866 (2)0.0590 (10)
C120.01801 (16)0.6538 (3)0.3276 (2)0.0476 (8)
C130.03172 (13)0.6628 (2)0.44022 (18)0.0352 (6)
C140.11081 (12)0.6336 (2)0.48077 (18)0.0340 (6)
C150.23791 (13)0.6310 (2)0.4926 (2)0.0391 (6)
C160.32228 (14)0.6578 (3)0.4792 (3)0.0637 (10)
C170.18724 (12)0.8055 (2)0.36715 (19)0.0348 (6)
C180.16505 (16)0.9329 (2)0.3999 (2)0.0441 (7)
C190.17852 (16)1.0418 (3)0.3320 (2)0.0497 (8)
C200.21503 (14)1.0236 (2)0.2313 (2)0.0456 (7)
C210.2375 (2)0.8955 (3)0.2002 (2)0.0612 (9)
C220.22377 (19)0.7867 (3)0.2674 (2)0.0575 (9)
H1−0.061 (2)0.684 (3)0.661 (3)0.0628*
H2−0.035780.639460.834740.0541*
H2A0.220 (2)1.195 (4)0.187 (4)0.0839*
H3−0.046120.686761.020180.0700*
H3A0.2334 (17)0.480 (3)0.608 (3)0.0492*
H40.006910.882001.090920.0768*
H50.072711.028260.977300.0778*
H60.084440.982610.791880.0616*
H9−0.147970.712050.514650.0573*
H10−0.169050.688500.329300.0696*
H11−0.065830.657940.211490.0710*
H120.059620.640810.279720.0571*
H16A0.331120.753520.477490.0956*
H16B0.350370.618820.539500.0956*
H16C0.340110.618300.411720.0956*
H180.141040.945520.467510.0529*
H190.163121.127830.353680.0596*
H210.262120.882570.133020.0734*
H220.239070.700600.245820.0689*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl0.0360 (2)0.0416 (3)0.0547 (3)−0.0066 (2)0.0002 (3)0.0095 (3)
O10.0540 (10)0.0641 (11)0.0389 (9)−0.0263 (9)0.0049 (8)−0.0019 (9)
O20.104 (2)0.0464 (10)0.0590 (13)0.0042 (12)0.0244 (13)0.0210 (11)
N10.0295 (9)0.0549 (12)0.0343 (10)−0.0086 (8)0.0027 (7)−0.0004 (9)
N20.0373 (9)0.0381 (9)0.0428 (10)−0.0018 (8)−0.0011 (8)0.0070 (9)
N30.0360 (9)0.0375 (9)0.0494 (11)0.0008 (8)−0.0005 (9)0.0105 (9)
N40.0345 (9)0.0309 (9)0.0382 (10)0.0006 (7)0.0047 (7)0.0034 (7)
C10.0332 (10)0.0399 (11)0.0362 (11)0.0028 (8)−0.0017 (9)0.0000 (9)
C20.0452 (13)0.0516 (14)0.0386 (12)−0.0102 (10)−0.0013 (10)0.0019 (11)
C30.0594 (16)0.075 (2)0.0406 (13)−0.0120 (14)0.0071 (12)0.0054 (14)
C40.083 (2)0.0655 (18)0.0435 (14)0.0084 (16)0.0101 (15)−0.0096 (14)
C50.094 (2)0.0415 (13)0.0588 (18)−0.0032 (14)0.0028 (17)−0.0158 (13)
C60.0678 (17)0.0380 (12)0.0481 (14)−0.0035 (11)0.0037 (13)0.0006 (10)
C70.0334 (11)0.0384 (11)0.0373 (11)−0.0034 (8)−0.0004 (9)0.0022 (9)
C80.0325 (10)0.0392 (11)0.0353 (10)−0.0063 (8)−0.0030 (8)0.0015 (9)
C90.0326 (10)0.0598 (15)0.0508 (14)−0.0082 (10)−0.0051 (10)0.0026 (12)
C100.0462 (14)0.0737 (18)0.0540 (16)−0.0104 (13)−0.0210 (13)0.0084 (14)
C110.0653 (18)0.075 (2)0.0367 (13)−0.0117 (15)−0.0159 (12)0.0048 (13)
C120.0534 (14)0.0549 (14)0.0346 (12)−0.0025 (11)−0.0022 (10)0.0006 (11)
C130.0366 (10)0.0353 (10)0.0337 (10)−0.0039 (8)−0.0027 (8)0.0040 (9)
C140.0359 (10)0.0325 (10)0.0336 (10)−0.0028 (8)0.0028 (8)0.0009 (8)
C150.0369 (12)0.0323 (9)0.0482 (12)0.0022 (8)0.0032 (10)0.0050 (10)
C160.0338 (13)0.0642 (18)0.093 (2)0.0031 (11)0.0058 (14)0.0277 (18)
C170.0365 (10)0.0309 (10)0.0369 (10)0.0006 (8)0.0046 (9)0.0054 (9)
C180.0518 (13)0.0379 (12)0.0425 (12)0.0099 (10)0.0153 (11)0.0057 (10)
C190.0625 (16)0.0339 (11)0.0527 (14)0.0139 (10)0.0168 (13)0.0069 (11)
C200.0533 (12)0.0394 (11)0.0440 (12)0.0020 (9)0.0076 (12)0.0113 (11)
C210.091 (2)0.0481 (14)0.0446 (14)0.0031 (14)0.0306 (15)0.0036 (11)
C220.086 (2)0.0351 (12)0.0515 (16)0.0072 (12)0.0283 (14)0.0009 (10)

Geometric parameters (Å, °)

O1—C71.218 (3)C8—C91.399 (3)
O2—C201.354 (3)C8—C131.395 (3)
O2—H2A0.76 (4)C9—C101.377 (4)
N1—C71.363 (3)C9—H90.9300
N1—C81.414 (3)C10—C111.371 (4)
N1—H10.81 (3)C10—H100.9300
N2—N31.369 (3)C11—C121.384 (4)
N2—C141.302 (3)C11—H110.9300
N3—C151.306 (3)C12—C131.396 (3)
N3—H3A0.97 (3)C12—H120.9300
N4—C141.385 (3)C13—C141.471 (3)
N4—C151.344 (3)C15—C161.479 (3)
N4—C171.443 (3)C16—H16A0.9600
C1—C21.385 (3)C16—H16B0.9600
C1—C61.380 (4)C16—H16C0.9600
C1—C71.494 (3)C17—C181.376 (3)
C2—C31.389 (4)C17—C221.380 (3)
C2—H20.9300C18—C191.378 (4)
C3—C41.373 (5)C18—H180.9300
C3—H30.9300C19—C201.390 (3)
C4—C51.371 (5)C19—H190.9300
C4—H40.9300C20—C211.378 (4)
C5—C61.388 (4)C21—C221.373 (4)
C5—H50.9300C21—H210.9300
C6—H60.9300C22—H220.9300
Cl···O2i3.090 (2)C21···O1iii3.291 (4)
Cl···N1ii3.372 (2)C22···C163.338 (4)
Cl···C2ii3.627 (3)C2···H19ix2.9700
Cl···N3iii3.068 (2)C2···H12.61 (4)
Cl···H2ii2.9400C4···H16Av2.9400
Cl···H9ii3.0700C5···H16Av2.8300
Cl···H1ii2.58 (3)C6···H16Av3.0600
Cl···H222.9400C8···H5vii2.9400
Cl···H10iv2.8800C9···H5vii2.7800
Cl···H2Ai2.34 (4)C12···H2ii2.9200
Cl···H3Aiii2.14 (3)C15···H21v3.0200
O1···N43.106 (3)C15···H223.0900
O1···N23.187 (3)C17···H16A2.8600
O1···C183.165 (3)C17···H122.9300
O1···C132.941 (3)H1···H92.3400
O1···C142.710 (3)H1···C22.61 (4)
O1···C21v3.291 (4)H1···Clviii2.58 (3)
O2···Clvi3.090 (2)H1···H22.2100
O1···H62.5200H2···N12.6300
O1···H182.3500H2···H12.2100
O1···H21v2.7100H2···C12viii2.9200
O2···H9vii2.8000H2···Clviii2.9400
N1···Clviii3.372 (2)H2A···H192.3500
N1···N23.141 (3)H2A···Clvi2.34 (4)
N2···C73.281 (3)H3···H11x2.3700
N2···N42.212 (3)H3···N2viii2.6700
N2···O13.187 (3)H3A···H16B2.5700
N2···N13.141 (3)H3A···Clv2.14 (3)
N3···Clv3.068 (2)H5···C9ix2.7800
N3···N42.124 (3)H5···C8ix2.9400
N4···N32.124 (3)H6···O12.5200
N4···O13.106 (3)H9···Clviii3.0700
N1···H22.6300H9···O2ix2.8000
N2···H3ii2.6700H9···H12.3400
N3···H22v2.9200H10···Clxi2.8800
N4···H122.8800H11···H3xii2.3700
C2···Clviii3.627 (3)H12···N42.8800
C3···C16v3.505 (4)H12···C172.9300
C4···C16v3.524 (4)H16A···C4iii2.9400
C7···N23.281 (3)H16A···C172.8600
C7···C143.105 (3)H16A···C5iii2.8300
C12···C173.301 (3)H16A···C6iii3.0600
C13···O12.941 (3)H16B···H3A2.5700
C13···C183.550 (3)H18···O12.3500
C14···O12.710 (3)H19···C2vii2.9700
C14···C73.105 (3)H19···H2A2.3500
C16···C223.338 (4)H21···C15iii3.0200
C16···C4iii3.524 (4)H21···O1iii2.7100
C16···C3iii3.505 (4)H22···C153.0900
C17···C123.301 (3)H22···N3iii2.9200
C18···C133.550 (3)H22···Cl2.9400
C18···O13.165 (3)
C20—O2—H2A112 (3)N4—C17—C18120.0 (2)
C7—N1—C8123.6 (2)C17—C18—C19119.7 (2)
N3—N2—C14103.89 (18)C18—C19—C20120.3 (2)
N2—N3—C15112.5 (2)O2—C20—C19122.9 (2)
C14—N4—C15106.23 (18)C19—C20—C21119.2 (2)
C14—N4—C17129.23 (18)O2—C20—C21117.9 (2)
C15—N4—C17124.32 (18)C20—C21—C22120.6 (2)
C8—N1—H1114 (3)C17—C22—C21119.8 (3)
C7—N1—H1117 (2)C1—C2—H2120.00
N2—N3—H3A119.5 (18)C3—C2—H2120.00
C15—N3—H3A128.0 (18)C2—C3—H3120.00
C2—C1—C6119.6 (2)C4—C3—H3120.00
C2—C1—C7122.9 (2)C3—C4—H4120.00
C6—C1—C7117.5 (2)C5—C4—H4120.00
C1—C2—C3119.8 (3)C4—C5—H5120.00
C2—C3—C4120.6 (3)C6—C5—H5120.00
C3—C4—C5119.5 (3)C1—C6—H6120.00
C4—C5—C6120.8 (3)C5—C6—H6120.00
C1—C6—C5119.8 (3)C8—C9—H9120.00
N1—C7—C1116.83 (19)C10—C9—H9120.00
O1—C7—N1121.7 (2)C9—C10—H10120.00
O1—C7—C1121.5 (2)C11—C10—H10120.00
C9—C8—C13119.0 (2)C10—C11—H11120.00
N1—C8—C13123.5 (2)C12—C11—H11120.00
N1—C8—C9117.5 (2)C11—C12—H12120.00
C8—C9—C10120.6 (2)C13—C12—H12120.00
C9—C10—C11120.5 (3)C15—C16—H16A109.00
C10—C11—C12119.9 (2)C15—C16—H16B109.00
C11—C12—C13120.5 (2)C15—C16—H16C109.00
C12—C13—C14118.2 (2)H16A—C16—H16B110.00
C8—C13—C12119.5 (2)H16A—C16—H16C109.00
C8—C13—C14122.0 (2)H16B—C16—H16C109.00
N2—C14—N4110.84 (18)C17—C18—H18120.00
N2—C14—C13124.17 (19)C19—C18—H18120.00
N4—C14—C13124.76 (19)C18—C19—H19120.00
N3—C15—N4106.5 (2)C20—C19—H19120.00
N4—C15—C16127.5 (2)C20—C21—H21120.00
N3—C15—C16126.0 (2)C22—C21—H21120.00
N4—C17—C22119.5 (2)C17—C22—H22120.00
C18—C17—C22120.3 (2)C21—C22—H22120.00
C8—N1—C7—O1−9.5 (3)C1—C2—C3—C4−0.2 (4)
C8—N1—C7—C1170.21 (19)C2—C3—C4—C5−0.7 (5)
C7—N1—C8—C9−130.2 (2)C3—C4—C5—C60.5 (5)
C7—N1—C8—C1349.5 (3)C4—C5—C6—C10.6 (5)
C14—N2—N3—C15−0.6 (3)N1—C8—C9—C10179.5 (2)
N3—N2—C14—N40.5 (2)C13—C8—C9—C10−0.2 (4)
N3—N2—C14—C13175.2 (2)N1—C8—C13—C12−177.8 (2)
N2—N3—C15—N40.4 (3)N1—C8—C13—C148.3 (3)
N2—N3—C15—C16−179.9 (2)C9—C8—C13—C121.9 (3)
C15—N4—C14—N2−0.2 (2)C9—C8—C13—C14−172.0 (2)
C15—N4—C14—C13−174.9 (2)C8—C9—C10—C11−1.6 (4)
C17—N4—C14—N2−175.0 (2)C9—C10—C11—C121.6 (5)
C17—N4—C14—C1310.4 (3)C10—C11—C12—C130.2 (4)
C14—N4—C15—N3−0.1 (2)C11—C12—C13—C8−1.9 (4)
C14—N4—C15—C16−179.8 (2)C11—C12—C13—C14172.2 (2)
C17—N4—C15—N3175.0 (2)C8—C13—C14—N252.0 (3)
C17—N4—C15—C16−4.7 (4)C8—C13—C14—N4−134.1 (2)
C14—N4—C17—C1867.0 (3)C12—C13—C14—N2−122.0 (3)
C14—N4—C17—C22−118.2 (3)C12—C13—C14—N452.0 (3)
C15—N4—C17—C18−106.9 (3)N4—C17—C18—C19175.6 (2)
C15—N4—C17—C2267.8 (3)C22—C17—C18—C190.9 (4)
C6—C1—C2—C31.3 (4)N4—C17—C22—C21−175.2 (3)
C7—C1—C2—C3−178.2 (2)C18—C17—C22—C21−0.5 (4)
C2—C1—C6—C5−1.5 (4)C17—C18—C19—C20−0.6 (4)
C7—C1—C6—C5178.0 (3)C18—C19—C20—O2−178.2 (3)
C2—C1—C7—O1−159.0 (2)C18—C19—C20—C210.1 (4)
C2—C1—C7—N121.3 (3)O2—C20—C21—C22178.7 (3)
C6—C1—C7—O121.5 (3)C19—C20—C21—C220.3 (4)
C6—C1—C7—N1−158.2 (2)C20—C21—C22—C17−0.1 (5)

Symmetry codes: (i) x, y−1, z; (ii) −x, −y+1, z−1/2; (iii) −x+1/2, y, z−1/2; (iv) x+1/2, −y+1, z; (v) −x+1/2, y, z+1/2; (vi) x, y+1, z; (vii) −x, −y+2, z−1/2; (viii) −x, −y+1, z+1/2; (ix) −x, −y+2, z+1/2; (x) x, y, z+1; (xi) x−1/2, −y+1, z; (xii) x, y, z−1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···Clviii0.81 (3)2.58 (3)3.372 (2)166 (3)
O2—H2A···Clvi0.76 (4)2.34 (4)3.090 (2)171 (5)
N3—H3A···Clv0.97 (3)2.14 (3)3.068 (2)158 (3)
C18—H18···O10.93002.35003.165 (3)146.00
C16—H16A···Cg2iii0.96002.84003.367 (3)115.00

Symmetry codes: (viii) −x, −y+1, z+1/2; (vi) x, y+1, z; (v) −x+1/2, y, z+1/2; (iii) −x+1/2, y, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2490).

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