organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

(Z)-1-(1,3-Di­phenyl-1H-pyrazol-4-yl)-N-phenyl­methanimine N-oxide

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aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, eChemistry Department, Faculty of Science, Assuit University, Egypt, fChemistry Department, College of Education, Salahaddin University-Hawler, Erbil, Kurdistan Region, Iraq, and gFaculty of Science, Department of Bio Chemistry, Beni Suef University, Beni Suef, Egypt
*Correspondence e-mail: shaabankamel@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 2 February 2018; accepted 3 February 2018; online 7 February 2018)

In the title nitrone, C22H17N3O, the dihedral angles between the central pyrazole ring and pendant N-bound, C-bound and nitrone-bound phenyl rings are 20.93 (6), 41.27 (6), and 32.57 (6)°, respectively. In the crystal, (101) layers are generated by C—H⋯O hydrogen bonds coupled with C—H⋯π(ring) and offset ππ stacking inter­actions.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Nitro­nes have various uses including as spin-trap reagents (Villamena et al., 2007[Villamena, F. A., Xia, S., Merle, J. K., Lauricella, R., Tuccio, B., Hadad, C. M. & Zweier, J. L. (2007). J. Am. Chem. Soc. 129, 8177-8191.]) and therapeutic agents (Piperno et al., 2010[Piperno, A., Giofrè, S. V., Iannazzo, D., Romeo, R., Romeo, G., Chiacchio, U., Rescifina, A. & Piotrowska, D. G. (2010). J. Org. Chem. 75, 2798-2805.]). They react in [3 + 2] dipolar cyclo­additions with carious dipolarophiles to construct functionalized isoxazolidines, which are useful inter­mediates in organic synthesis (Dell, 1998[Dell, C. P. (1998). J. Chem. Soc. Perkin Trans. 1, pp. 3873-3905.]). As part of our studies in this area, we report herein the synthesis and crystal structure of the title compound (Fig. 1[link]).

[Figure 1]
Figure 1
The title mol­ecule, shown with 50% probability displacement ellipsoids.

The dihedral angle between the pyrazole and the C4–C9 rings is 41.27 (6)°; those between the pyrazole and the C11–C16 and C17–C22 rings are, respectively, 32.57 (6) and 20.93 (6)°.

In the crystal, zigzag chains along the c-axis direction are generated by C6—H6⋯O1 and C7—H7⋯O1 hydrogen bonds (Table 1[link] and Figs. 2[link] and 3[link]). These are connected into layers parallel to the ac plane by C5—H5⋯O1 hydrogen bonds, three C—H⋯π(ring) inter­actions (Table 1[link]) and offset ππ stacking inter­actions between inversion-related C17–C22 rings [centroid–centroid distance = 3.6187 (8) Å](Figs. 2[link] and 3[link]).

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are, respectively, the centroids of the C4–C9 and C11–C16 benzene rings.

D—H⋯A D—H H⋯A DA D—H⋯A
C5—H5⋯O1i 0.979 (15) 2.303 (15) 3.2561 (14) 164.1 (11)
C6—H6⋯O1ii 0.988 (15) 2.514 (15) 3.1746 (14) 124.1 (11)
C7—H7⋯O1ii 1.003 (15) 2.544 (15) 3.1837 (14) 121.4 (11)
C9—H9⋯Cg3iii 0.975 (14) 2.764 (14) 3.6409 (13) 152.8 (11)
C14—H14⋯Cg2iv 0.988 (17) 2.884 (16) 3.6249 (14) 132.5 (12)
C19—H19⋯Cg2i 1.003 (17) 2.678 (17) 3.6128 (14) 155.3 (12)
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) x, y+1, z.
[Figure 2]
Figure 2
Details of the inter­molecular inter­actions. C—H⋯O hydrogen bonds are shown by black dashed lines while C—H⋯π(ring) and offset ππ stacking inter­actions are shown, respectively, by green and orange dashed lines.
[Figure 3]
Figure 3
Packing viewed along the a-axis direction, with inter­molecular inter­actions shown as depicted in Fig. 2[link].

Synthesis and crystallization

A solution of (20 g, 0.08 mol) 1,3-diphenyl 4-formyl pyrazole in ethanol (20 ml) was added to a solution of (9.0 g, 0.08 mol) N-phenyl­hydroxy­amine in ethanol (50 ml) and the mixture was heated under reflux for 2 h. The product was separated in 92% yield (25 g) and recrystallized from ethanol solution to afford colourless slabs; m.p. 431 K.

FTIR (KBr) (cm−1): 3150 (Ar. C—H), 3050 (H—C=N+), 1597 (C=N), 1579 (C=N+). 1H-NMR spectrum: δ p.p.m. (400 MHz, CDCl3) 7.3–8.1 (m, 16H, Ar H), 9.9 (s, 1H, CH=N+). Proton decoupled 13C NMR spectrum: δ (100.5 MHz, CDCl3) 113.2, 119.5, 127.2, 128.9, 129.0, 129.1, 129.3, 129.6, 129.8, 129.8, 132.3, 139.6, 147.9, 153.8 (15 Ar C). Mass spectrum (electron impact): e/m (%) 339.2 (1/2), 286.8 (100), 219.1 (58). Analysis calculated for (C22H17N3O) (%): C 77.86, H 5.05, N 12.38. Found; C 77.27, H 5.02, N 12.38.

Refinement

Crystal and refinement details are presented in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C22H17N3O
Mr 339.38
Crystal system, space group Monoclinic, P21/c
Temperature (K) 150
a, b, c (Å) 9.1084 (8), 10.8314 (9), 17.2226 (14)
β (°) 94.060 (3)
V3) 1694.9 (2)
Z 4
Radiation type Cu Kα
μ (mm−1) 0.66
Crystal size (mm) 0.24 × 0.21 × 0.10
 
Data collection
Diffractometer Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction Multi-scan (SADABS; Krause et al., 2015[Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3-10.])
Tmin, Tmax 0.85, 0.94
No. of measured, independent and observed [I > 2σ(I)] reflections 12691, 3366, 3115
Rint 0.028
(sin θ/λ)max−1) 0.625
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.086, 1.06
No. of reflections 3366
No. of parameters 304
H-atom treatment All H-atom parameters refined
Δρmax, Δρmin (e Å−3) 0.25, −0.19
Computer programs: APEX3 and SAINT (Bruker, 2016[Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS, Inc., Madison, WI.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2016 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND, Crystal Impact GbR, Bonn, Germany.]) and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Structural data


Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(Z)-1-(1,3-Diphenyl-1H-pyrazol-4-yl)-N-phenylmethanimine N-oxide top
Crystal data top
C22H17N3OF(000) = 712
Mr = 339.38Dx = 1.330 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 9.1084 (8) ÅCell parameters from 9914 reflections
b = 10.8314 (9) Åθ = 4.8–74.6°
c = 17.2226 (14) ŵ = 0.66 mm1
β = 94.060 (3)°T = 150 K
V = 1694.9 (2) Å3Slab, colourless
Z = 40.24 × 0.21 × 0.10 mm
Data collection top
Bruker D8 VENTURE PHOTON 100 CMOS
diffractometer
3366 independent reflections
Radiation source: INCOATEC IµS micro-focus source3115 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.028
Detector resolution: 10.4167 pixels mm-1θmax = 74.6°, θmin = 4.8°
ω scansh = 109
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
k = 1312
Tmin = 0.85, Tmax = 0.94l = 2119
12691 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035All H-atom parameters refined
wR(F2) = 0.086 w = 1/[σ2(Fo2) + (0.0366P)2 + 0.5699P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
3366 reflectionsΔρmax = 0.25 e Å3
304 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXL2016 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0046 (4)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 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) top
xyzUiso*/Ueq
O10.28419 (9)0.52663 (7)0.36611 (4)0.0258 (2)
N10.47211 (10)0.17352 (8)0.35347 (5)0.0215 (2)
N20.43135 (10)0.11254 (8)0.28595 (5)0.0224 (2)
N30.24264 (10)0.51508 (8)0.29270 (5)0.0204 (2)
C10.34438 (12)0.19128 (10)0.24500 (6)0.0210 (2)
C20.32853 (12)0.30422 (10)0.28615 (6)0.0213 (2)
C30.41176 (12)0.28765 (10)0.35573 (6)0.0225 (2)
H30.4284 (15)0.3403 (13)0.4012 (8)0.033 (4)*
C40.28057 (12)0.15709 (10)0.16696 (6)0.0209 (2)
C50.36634 (12)0.09282 (10)0.11610 (7)0.0233 (2)
H50.4686 (16)0.0721 (13)0.1323 (8)0.030 (4)*
C60.30717 (13)0.06002 (10)0.04264 (7)0.0248 (2)
H60.3662 (16)0.0143 (14)0.0062 (9)0.033 (4)*
C70.16261 (13)0.08928 (11)0.01886 (7)0.0264 (3)
H70.1217 (16)0.0663 (13)0.0348 (9)0.032 (4)*
C80.07650 (13)0.15151 (11)0.06946 (7)0.0278 (3)
H80.0281 (17)0.1681 (14)0.0528 (9)0.037 (4)*
C90.13483 (12)0.18579 (10)0.14310 (7)0.0242 (2)
H90.0741 (16)0.2279 (13)0.1793 (8)0.030 (3)*
C100.25703 (12)0.41252 (10)0.25391 (6)0.0221 (2)
H100.2241 (15)0.4182 (12)0.1985 (8)0.026 (3)*
C110.18754 (12)0.62568 (10)0.25287 (6)0.0211 (2)
C120.07684 (13)0.62002 (11)0.19349 (7)0.0266 (3)
H120.0327 (17)0.5402 (15)0.1778 (9)0.041 (4)*
C130.02996 (15)0.72902 (12)0.15667 (7)0.0320 (3)
H130.0492 (18)0.7239 (15)0.1140 (10)0.044 (4)*
C140.09319 (15)0.84091 (12)0.17922 (8)0.0328 (3)
H140.0611 (18)0.9174 (15)0.1518 (9)0.046 (4)*
C150.20296 (15)0.84466 (11)0.23889 (8)0.0329 (3)
H150.2490 (18)0.9228 (16)0.2557 (9)0.046 (4)*
C160.25028 (13)0.73711 (11)0.27657 (7)0.0275 (3)
H160.3280 (16)0.7378 (13)0.3209 (9)0.033 (4)*
C170.57182 (12)0.11615 (10)0.40996 (6)0.0222 (2)
C180.58624 (13)0.01172 (11)0.40974 (7)0.0246 (2)
H180.5275 (16)0.0599 (13)0.3711 (8)0.030 (4)*
C190.68443 (14)0.06779 (12)0.46408 (7)0.0309 (3)
H190.6950 (17)0.1599 (16)0.4635 (9)0.042 (4)*
C200.76560 (14)0.00264 (13)0.51877 (8)0.0358 (3)
H200.8351 (19)0.0370 (16)0.5572 (10)0.050 (5)*
C210.74840 (15)0.12980 (13)0.51930 (8)0.0369 (3)
H210.803 (2)0.1830 (17)0.5598 (10)0.055 (5)*
C220.65314 (14)0.18760 (12)0.46431 (7)0.0307 (3)
H220.6438 (17)0.2784 (15)0.4628 (9)0.039 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0310 (4)0.0277 (4)0.0179 (4)0.0011 (3)0.0025 (3)0.0018 (3)
N10.0239 (5)0.0209 (5)0.0192 (4)0.0005 (3)0.0005 (4)0.0000 (3)
N20.0253 (5)0.0216 (5)0.0199 (4)0.0002 (3)0.0010 (4)0.0012 (3)
N30.0205 (5)0.0211 (5)0.0195 (4)0.0004 (3)0.0009 (3)0.0003 (3)
C10.0217 (5)0.0199 (5)0.0214 (5)0.0008 (4)0.0019 (4)0.0012 (4)
C20.0226 (5)0.0202 (5)0.0214 (5)0.0001 (4)0.0026 (4)0.0003 (4)
C30.0252 (6)0.0203 (5)0.0219 (5)0.0003 (4)0.0020 (4)0.0007 (4)
C40.0238 (5)0.0173 (5)0.0213 (5)0.0013 (4)0.0000 (4)0.0015 (4)
C50.0227 (6)0.0225 (5)0.0245 (5)0.0023 (4)0.0006 (4)0.0008 (4)
C60.0281 (6)0.0230 (5)0.0230 (6)0.0011 (4)0.0016 (4)0.0012 (4)
C70.0302 (6)0.0245 (6)0.0237 (6)0.0018 (4)0.0047 (5)0.0001 (4)
C80.0237 (6)0.0267 (6)0.0321 (6)0.0009 (4)0.0052 (5)0.0000 (5)
C90.0229 (6)0.0221 (5)0.0278 (6)0.0008 (4)0.0022 (4)0.0010 (4)
C100.0240 (6)0.0220 (5)0.0201 (5)0.0005 (4)0.0015 (4)0.0001 (4)
C110.0222 (5)0.0208 (5)0.0207 (5)0.0021 (4)0.0040 (4)0.0012 (4)
C120.0287 (6)0.0233 (6)0.0272 (6)0.0010 (4)0.0016 (5)0.0012 (4)
C130.0363 (7)0.0300 (6)0.0287 (6)0.0057 (5)0.0037 (5)0.0023 (5)
C140.0419 (7)0.0241 (6)0.0324 (6)0.0057 (5)0.0029 (5)0.0059 (5)
C150.0381 (7)0.0209 (6)0.0395 (7)0.0015 (5)0.0011 (5)0.0005 (5)
C160.0283 (6)0.0237 (6)0.0301 (6)0.0009 (4)0.0003 (5)0.0013 (5)
C170.0208 (5)0.0258 (6)0.0198 (5)0.0002 (4)0.0011 (4)0.0030 (4)
C180.0266 (6)0.0261 (6)0.0213 (5)0.0034 (4)0.0023 (4)0.0007 (4)
C190.0327 (7)0.0313 (7)0.0287 (6)0.0086 (5)0.0026 (5)0.0037 (5)
C200.0297 (7)0.0442 (7)0.0323 (7)0.0036 (5)0.0061 (5)0.0094 (6)
C210.0337 (7)0.0415 (7)0.0336 (7)0.0096 (5)0.0102 (5)0.0044 (6)
C220.0321 (6)0.0283 (6)0.0307 (6)0.0064 (5)0.0053 (5)0.0022 (5)
Geometric parameters (Å, º) top
O1—N31.2999 (11)C10—H100.982 (14)
N1—C31.3546 (14)C11—C161.3845 (16)
N1—N21.3657 (12)C11—C121.3857 (16)
N1—C171.4257 (13)C12—C131.3927 (16)
N2—C11.3316 (14)C12—H120.983 (16)
N3—C101.3076 (14)C13—C141.3855 (18)
N3—C111.4523 (13)C13—H130.994 (16)
C1—C21.4262 (15)C14—C151.3828 (18)
C1—C41.4733 (14)C14—H140.988 (17)
C2—C31.3836 (15)C15—C161.3872 (17)
C2—C101.4343 (15)C15—H150.980 (17)
C3—H30.973 (15)C16—H161.003 (15)
C4—C91.3966 (16)C17—C221.3875 (16)
C4—C51.3997 (16)C17—C181.3912 (16)
C5—C61.3859 (16)C18—C191.3878 (16)
C5—H50.979 (14)C18—H180.976 (15)
C6—C71.3877 (17)C19—C201.3846 (19)
C6—H60.988 (15)C19—H191.003 (17)
C7—C81.3878 (17)C20—C211.386 (2)
C7—H71.002 (14)C20—H200.982 (17)
C8—C91.3903 (16)C21—C221.3876 (17)
C8—H80.992 (15)C21—H211.009 (18)
C9—H90.975 (14)C22—H220.987 (16)
C3—N1—N2112.30 (9)C16—C11—C12121.32 (10)
C3—N1—C17128.19 (9)C16—C11—N3117.27 (10)
N2—N1—C17119.47 (9)C12—C11—N3121.41 (10)
C1—N2—N1104.89 (9)C11—C12—C13118.82 (11)
O1—N3—C10123.09 (9)C11—C12—H12120.3 (9)
O1—N3—C11116.56 (8)C13—C12—H12120.9 (9)
C10—N3—C11120.21 (9)C14—C13—C12120.39 (11)
N2—C1—C2111.32 (9)C14—C13—H13121.4 (9)
N2—C1—C4120.24 (10)C12—C13—H13118.2 (9)
C2—C1—C4128.43 (10)C15—C14—C13119.89 (11)
C3—C2—C1104.51 (9)C15—C14—H14120.4 (9)
C3—C2—C10130.34 (10)C13—C14—H14119.7 (9)
C1—C2—C10124.64 (10)C14—C15—C16120.49 (12)
N1—C3—C2106.98 (9)C14—C15—H15121.2 (10)
N1—C3—H3121.2 (8)C16—C15—H15118.4 (10)
C2—C3—H3131.8 (8)C11—C16—C15119.08 (11)
C9—C4—C5119.18 (10)C11—C16—H16119.0 (8)
C9—C4—C1121.19 (10)C15—C16—H16121.9 (8)
C5—C4—C1119.62 (10)C22—C17—C18120.74 (11)
C6—C5—C4120.04 (10)C22—C17—N1120.07 (10)
C6—C5—H5120.1 (8)C18—C17—N1119.19 (10)
C4—C5—H5119.8 (8)C19—C18—C17119.36 (11)
C5—C6—C7120.69 (11)C19—C18—H18121.5 (8)
C5—C6—H6120.9 (8)C17—C18—H18119.2 (8)
C7—C6—H6118.4 (8)C20—C19—C18120.35 (12)
C6—C7—C8119.49 (11)C20—C19—H19120.5 (9)
C6—C7—H7119.9 (8)C18—C19—H19119.1 (9)
C8—C7—H7120.6 (8)C19—C20—C21119.78 (12)
C7—C8—C9120.41 (11)C19—C20—H20120.4 (10)
C7—C8—H8118.7 (9)C21—C20—H20119.8 (10)
C9—C8—H8120.9 (9)C20—C21—C22120.61 (12)
C8—C9—C4120.19 (11)C20—C21—H21121.5 (10)
C8—C9—H9120.7 (8)C22—C21—H21117.9 (10)
C4—C9—H9119.1 (8)C17—C22—C21119.14 (12)
N3—C10—C2123.79 (10)C17—C22—H22119.8 (9)
N3—C10—H10114.1 (8)C21—C22—H22121.1 (9)
C2—C10—H10121.8 (8)
C3—N1—N2—C10.49 (12)C3—C2—C10—N310.05 (19)
C17—N1—N2—C1177.46 (9)C1—C2—C10—N3179.52 (11)
N1—N2—C1—C20.02 (12)O1—N3—C11—C1633.72 (14)
N1—N2—C1—C4179.05 (9)C10—N3—C11—C16142.14 (11)
N2—C1—C2—C30.49 (13)O1—N3—C11—C12146.36 (10)
C4—C1—C2—C3179.42 (11)C10—N3—C11—C1237.78 (15)
N2—C1—C2—C10171.98 (10)C16—C11—C12—C130.83 (18)
C4—C1—C2—C106.94 (18)N3—C11—C12—C13179.08 (10)
N2—N1—C3—C20.81 (13)C11—C12—C13—C140.01 (19)
C17—N1—C3—C2176.91 (10)C12—C13—C14—C150.3 (2)
C1—C2—C3—N10.76 (12)C13—C14—C15—C160.1 (2)
C10—C2—C3—N1171.12 (11)C12—C11—C16—C151.28 (18)
N2—C1—C4—C9138.67 (11)N3—C11—C16—C15178.64 (11)
C2—C1—C4—C942.49 (17)C14—C15—C16—C110.91 (19)
N2—C1—C4—C540.22 (15)C3—N1—C17—C2219.80 (17)
C2—C1—C4—C5138.62 (12)N2—N1—C17—C22157.78 (11)
C9—C4—C5—C60.95 (16)C3—N1—C17—C18160.22 (11)
C1—C4—C5—C6179.86 (10)N2—N1—C17—C1822.20 (15)
C4—C5—C6—C70.57 (17)C22—C17—C18—C190.72 (17)
C5—C6—C7—C80.32 (18)N1—C17—C18—C19179.27 (10)
C6—C7—C8—C90.81 (18)C17—C18—C19—C201.00 (18)
C7—C8—C9—C40.42 (18)C18—C19—C20—C210.1 (2)
C5—C4—C9—C80.46 (17)C19—C20—C21—C221.6 (2)
C1—C4—C9—C8179.35 (10)C18—C17—C22—C210.69 (19)
O1—N3—C10—C24.28 (17)N1—C17—C22—C21179.32 (11)
C11—N3—C10—C2171.30 (10)C20—C21—C22—C171.8 (2)
Hydrogen-bond geometry (Å, º) top
Cg2 and Cg3 are, respectively, the centroids of the C4–C9 and C11–C16 benzene rings.
D—H···AD—HH···AD···AD—H···A
C5—H5···O1i0.979 (15)2.303 (15)3.2561 (14)164.1 (11)
C6—H6···O1ii0.988 (15)2.514 (15)3.1746 (14)124.1 (11)
C7—H7···O1ii1.003 (15)2.544 (15)3.1837 (14)121.4 (11)
C9—H9···Cg3iii0.975 (14)2.764 (14)3.6409 (13)152.8 (11)
C14—H14···Cg2iv0.988 (17)2.884 (16)3.6249 (14)132.5 (12)
C19—H19···Cg2i1.003 (17)2.678 (17)3.6128 (14)155.3 (12)
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y+1/2, z1/2; (iii) x, y1/2, z+1/2; (iv) x, y+1, z.
 

Funding information

The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

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