4-Benzyl-1-(4-nitro-phen-yl)-1H-1,2,3-triazole: crystal structure and Hirshfeld analysis.

The mol-ecule in the title compound, C15H12N4O2, has a twisted L-shape with the dihedral angle between the aromatic rings of the N-bound benzene and C-bound benzyl groups being 70.60 (9)°. The nitro group is co-planar with the benzene ring to which it is connected [C-C-N-O torsion angle = 0.4 (3)°]. The three-dimensional packing is stabilized by a combination of methyl-ene-C-H⋯O(nitro), methyl-ene-C-H⋯π(phen-yl), phenyl-C-H⋯π(triazol-yl) and nitro-O⋯π(nitro-benzene) inter-actions, along with weak π(triazol-yl)-π(nitrobenzene) contacts [inter-centroid distance = 3.8386 (10) Å]. The importance of the specified inter-molecular contacts has been verified by an analysis of the calculated Hirshfeld surface.

Chemical context

The 1,2,3-triazoles comprise an important class of mol­ecules, having a number of applications in biology and materials science. As reviewed recently, 1,2,3-triazoles display various potential pharmaceutical properties including anti-cancer, anti-viral, anti-tuberculosis and anti-microbial activities (Tron et al., 2008 ▸; Thirumurugan et al., 2013 ▸). The 1,2,3-triazole chromo­phore can function as a most useful scaffold in bio-conjugation owing to its rigid framework, stability, and, crucially, water-solubility (Jewett & Bertozzi, 2010 ▸; Holub & Kirshenbaum, 2010 ▸). Further applications are known in the fields of dyes, photostabilizers and as agrochemicals (Golas & Matyjaszewski, 2010 ▸; Qin et al., 2010 ▸). Very recently, a new and efficient synthesis for a metal-free and regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles was described (Ali et al., 2014 ▸). Among the compounds synthesized in that study was the title compound, (I). Herein, the crystal and mol­ecular structures of (I) are described along with an analysis of the Hirshfeld surface.

Structural commentary

The mol­ecular structure of (I), Fig. 1 ▸, comprises a central, strictly planar 1,2,3-triazolyl ring (r.m.s. deviation of the five fitted atoms = 0.001 Å) flanked by C- and N-bound benzyl and 4-nitro­benzene substituents, respectively. The dihedral angle between the five-membered ring and phenyl ring is 83.23 (10)°, indicating a near perpendicular relationship. By contrast, the benzene ring is closer to co-planar to the triazolyl ring, forming a dihedral angle of 13.95 (9)°. The dihedral angle between the outer rings is 70.60 (9)°, indicating that the mol­ecule has a skewed-shape based on the letter L. The nitro group is co-planar with the benzene ring to which it is bound as seen in the value of the C12—C13—N4—O1 torsion angle of 0.4 (3)°.

Figure 1

The mol­ecular structure of (I), showing the atom-labelling scheme and displacement ellipsoids at the 35% probability level.

Supra­molecular features

The mol­ecular packing of (I) features methyl­ene-C—H⋯O(nitro), methyl­ene-C—H⋯π(phen­yl), phenyl-C—H⋯π(triazol­yl) and nitro-O⋯π(nitro­benzene) inter­actions, Table 1 ▸; the latter inter­actions have been described as being important in stabilizing the crystal packing of nitro-containing compounds (Huang et al., 2008 ▸). The C—H⋯O and nitro-O⋯π inter­actions occur between centrosymmetrically related mol­ecules while the C—H⋯π(phen­yl) contacts occur along the a-axis direction and the C—H⋯π(triazol­yl) contacts along the b-axis direction and, all taken together, consolidate the three-dimensional architecture, Fig. 2 ▸. Within the specified framework, weak π(triazol­yl)–π(nitro­benzene)i inter­actions occur with the inter-centroid distance = 3.8386 (10) Å, inter-planar angle = 13.95 (9)° for symmetry code: (i) 1 − x, − y, 2 − z.

Table 1

Hydrogen-bond geometry (Å, °)

Cg1–Cg3 are the centroids of the N1–N3,C1,C2, C4–C9 and C10-C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3B⋯O2i	0.97	2.58	3.452 (3)	150
C3—H3A⋯Cg2ii	0.97	2.96	3.857 (2)	154
C8—H8⋯Cg1iii	0.93	2.86	3.665 (3)	146
N4—O1⋯Cg3iv	1.21 (1)	3.67 (1)	4.1254 (19)	103 (1)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

Figure 2

A view of the unit-cell contents in projection down the a axis. The C—H⋯O, C—H⋯π and nitro-O⋯π contacts are shown as orange, purple and blue dashed lines, respectively.

Hirshfeld surface analysis

The study of the Hirshfeld surface and inter­molecular inter­actions of (I) has been carried out using standard parameters of the CrystalExplorer package (Wolff et al., 2012 ▸) and using similar protocols as in earlier studies (Zukerman-Schpector et al., 2017 ▸). In (I), the Hirshfeld surface is controlled by attractive inter­actions such as non-conventional C—H⋯π, C—H⋯O, C—H⋯N hydrogen bonds and π–π inter­actions. The aforementioned contacts contribute around 70% to the overall surface area, Fig. 3 ▸ and Table 2 ▸. The repulsive H⋯H inter­actions account for the remaining 30%, Fig. 3 ▸ b. These observations may be rationalized in terms of the structure having electron-rich groups, i.e. the three aromatic rings and the nitro substituent, for which the electron densities are highly delocal­ized allowing them to have significant overlap in the mol­ecular packing.

Figure 3

(a) The full two-dimensional fingerprint plot for (I) and two views of the Hirshfeld surface mapped over the shape-index property, and fingerprint plots delineated into (b) H⋯H, (c) C⋯H/H⋯C, (d) O⋯H/H⋯O, (e) N⋯H/H⋯N, (f) C⋯N/N⋯C and (g) C⋯O/O⋯C inter­atomic contacts along with two views of Hirshfeld surface mapped over shape-index.

Table 2

Percentage contributions of inter­atomic contacts to the Hirshfeld surface for (I)

Contact	Percentage contribution
H⋯H	28.7
C⋯H/H⋯C	26.1
O⋯H/H⋯O	21.0
N⋯H/H⋯N	15.6
C⋯N/N⋯C	3.9
C⋯O/O⋯C	2.4
others	2.3

As attractive inter­actions, the C⋯H/H⋯C contacts contribute a significant role (26.1%) to the overall surface area. These contacts arise mainly from C—H⋯π contacts spread over the entire mol­ecule in which all rings, i.e. the triazole, nitro­benzene and benzyl rings, function as H-atom acceptors, Tables 1 ▸ and 3 ▸, and Fig. 3 ▸ c. The O⋯H/H⋯O contacts contribute 21.0% to the Hirshfeld surface area. In essence, this arises owing to non-conventional C—H⋯O hydrogen bonds, Fig. 3 ▸ d. There are two different H-donor carbon atoms participating in the weak C—H⋯O inter­actions, one of which is the methyl­ene-C3 atom, Table 1 ▸, and the other being the nitro­benzene-C12 atom, Table 3 ▸. The N⋯H/H⋯N contacts contribute approximately 16% to the overall surface area, Fig. 3 ▸ e. Non conventional C—H⋯N hydrogen bonds are formed with nitro­benzene-C atoms as H-atom donors, Table 3 ▸ and Fig. 3 ▸ f. The C⋯N/N⋯C and C⋯O/O⋯C contacts contribute around 6% to the Hirshfeld surface, Table 2 ▸ and Fig. 3 ▸ f and g. Other surface contacts do not contribute significantly to the mol­ecular packing.

Table 3

Summary of short inter­atomic contacts (Å) in (I)

Contact	Distance	Symmetry operation
H15⋯H15	2.54	2 − x, −y, 2 − z
C7⋯H11	2.78	1 − x, −  + y,  − z
O1⋯H12	2.62	−x, 1 − y, 2 − z
O1⋯C13	3.386 (3)	1 − x, 1 − y, 2 − z
C15⋯N1	3.413 (2)	1 − x, −y, 2 − z
H15⋯N2	2.71	2 − x, −y, 2 − z
H14⋯N3	3.00	2 − x, −y, 2 − z

Database survey

There are only relatively few 1,2,3-triazole structures in the literature having N-bound aryl groups and C-bound alkyl substituents. The two mol­ecules closest to (I) have N-bound 4-chloro­benzene and C-bound n-butyl groups, i.e. (II) (Sarode et al., 2016 ▸), and N-bound 4-nitro­benzene and C-bound n-hexyl groups, i.e. (III) (Muhammad et al., 2015 ▸). In (II), the dihedral angle between the two planes is 22.59 (7)° and the n-butyl group is co-planar with the the five-membered ring as seen in the sp 2-C—Cquaternary—C—Cmethyl­ene = 0.06 (4)° and Cmethyl­ene—C—C—Cmeth­yl = −177.39 (19)° torsion angles. In (III), the aromatic rings are considerably more co-planar, cf. (I) and (II), with the dihedral angle between them being 2.65 (8)°. With respect to the n-hexyl substituent, the structure of (III) resembles that of (I) in that the sp 2-C—Cquaternary—C—Cmethyl­ene torsion angle is −118.4 (3)°.

Synthesis and crystallization

The title compound was prepared as described in the literature (Ali et al., 2014 ▸). Crystals of (I) for the X-ray study were obtained by slow evaporation from an ethyl acetate/n-hexane solution (5:1 v/v). 1H NMR (400 MHz, CDCl3) δ 7.70–7.65 (m, 2H), 7.59 (s, 1H), 7.51–7.45 (m, 2H), 7.42–7.32 (m, 3H), 7.31–7.21 (m, 2H), 4.17 (s, 2H). 13C NMR (100 MHz, CDCl3) δ = 148.5, 138.8, 137.2, 129.6, 128.8, 128.7, 128.5, 126.6, 120.42, 119.6, 32.3 ppm. ESI–MS (m/z) calculated for C15H12N4O2 [M + H]+ 281.1038, found 281.1039.

Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 4 ▸. The carbon-bound H atoms were placed in calculated positions (C—H = 0.93–0.97 Å) and were included in the refinement in the riding-model approximation, with U iso(H) set to 1.2U eq(C).

Table 4

Experimental details

Crystal data
Chemical formula	C15H12N4O2
M r	280.29
Crystal system, space group	Monoclinic, P21/c
Temperature (K)	293
a, b, c (Å)	5.1962 (1), 10.7814 (3), 24.0067 (6)
β (°)	90.256 (2)
V (Å3)	1344.90 (6)
Z	4
Radiation type	Mo Kα
μ (mm−1)	0.10
Crystal size (mm)	0.46 × 0.26 × 0.14
Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996 ▸)
T min, T max	0.695, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	9104, 2450, 1881
R int	0.023
(sin θ/λ)max (Å−1)	0.603
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S	0.040, 0.106, 1.06
No. of reflections	2450
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρmax, Δρmin (e Å−3)	0.16, −0.18

Computer programs: APEX2 and SAINT (Bruker, 2009 ▸), SIR2014 (Burla et al., 2015 ▸), SHELXL2014 (Sheldrick, 2015 ▸), ORTEP-3 for Windows (Farrugia, 2012 ▸), DIAMOND (Brandenburg, 2006 ▸), MarvinSketch (ChemAxon, 2010 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989017014748/hg5498sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989017014748/hg5498Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989017014748/hg5498Isup3.cml

CCDC reference: 1579464

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H12N4O2	Dx = 1.384 Mg m−3
Mr = 280.29	Melting point = 371–373 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.1962 (1) Å	Cell parameters from 2937 reflections
b = 10.7814 (3) Å	θ = 3.2–25.0°
c = 24.0067 (6) Å	µ = 0.10 mm−1
β = 90.256 (2)°	T = 293 K
V = 1344.90 (6) Å3	Irregular, yellow
Z = 4	0.46 × 0.26 × 0.14 mm
F(000) = 584

Bruker APEXII CCD diffractometer	1881 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.023
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	θmax = 25.4°, θmin = 1.7°
Tmin = 0.695, Tmax = 0.745	h = −6→6
9104 measured reflections	k = −12→12
2450 independent reflections	l = −28→28

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0383P)2 + 0.3766P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2450 reflections	Δρmax = 0.16 e Å−3
190 parameters	Δρmin = −0.18 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.6006 (3)	−0.10629 (18)	0.84523 (7)	0.0532 (4)
C2	0.4648 (3)	−0.01241 (18)	0.86767 (6)	0.0531 (4)
H2	0.3030	0.0154	0.8566	0.064*
C3	0.5294 (4)	−0.1916 (2)	0.79835 (7)	0.0672 (5)
H3A	0.3644	−0.1662	0.7832	0.081*
H3B	0.5100	−0.2750	0.8129	0.081*
C4	0.7242 (3)	−0.19387 (16)	0.75201 (7)	0.0519 (4)
C5	0.7534 (4)	−0.09304 (18)	0.71743 (8)	0.0646 (5)
H5	0.6472	−0.0244	0.7220	0.078*
C6	0.9359 (4)	−0.0918 (2)	0.67636 (8)	0.0762 (6)
H6	0.9520	−0.0224	0.6536	0.091*
C7	1.0933 (4)	−0.1905 (3)	0.66847 (9)	0.0803 (7)
H7	1.2195	−0.1884	0.6411	0.096*
C8	1.0641 (4)	−0.2926 (3)	0.70110 (10)	0.0836 (7)
H8	1.1682	−0.3616	0.6954	0.100*
C9	0.8791 (4)	−0.29477 (19)	0.74304 (8)	0.0695 (5)
H9	0.8607	−0.3651	0.7651	0.083*
C10	0.5585 (3)	0.13033 (15)	0.94757 (6)	0.0444 (4)
C11	0.3575 (3)	0.21075 (18)	0.93671 (7)	0.0577 (5)
H11	0.2615	0.2024	0.9041	0.069*
C12	0.2992 (4)	0.30319 (18)	0.97405 (8)	0.0627 (5)
H12	0.1625	0.3569	0.9674	0.075*
C13	0.4468 (3)	0.31461 (16)	1.02137 (7)	0.0541 (4)
C14	0.6508 (3)	0.23726 (17)	1.03240 (7)	0.0562 (4)
H14	0.7494	0.2478	1.0645	0.067*
C15	0.7071 (3)	0.14397 (17)	0.99526 (6)	0.0511 (4)
H15	0.8439	0.0904	1.0021	0.061*
N1	0.6118 (2)	0.03310 (13)	0.90952 (5)	0.0451 (3)
N2	0.8341 (3)	−0.03164 (15)	0.91281 (6)	0.0583 (4)
N3	0.8269 (3)	−0.11635 (15)	0.87374 (6)	0.0628 (4)
N4	0.3812 (4)	0.41242 (16)	1.06168 (7)	0.0729 (5)
O1	0.1984 (4)	0.47864 (19)	1.05159 (8)	0.1170 (7)
O2	0.5137 (4)	0.42327 (16)	1.10290 (7)	0.1031 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0419 (9)	0.0744 (12)	0.0432 (8)	−0.0121 (8)	0.0010 (7)	0.0016 (8)
C2	0.0367 (8)	0.0806 (13)	0.0420 (8)	−0.0047 (8)	−0.0035 (7)	0.0027 (8)
C3	0.0609 (11)	0.0851 (14)	0.0556 (10)	−0.0213 (10)	0.0005 (9)	−0.0091 (10)
C4	0.0513 (10)	0.0585 (11)	0.0458 (8)	−0.0051 (8)	−0.0084 (7)	−0.0099 (8)
C5	0.0728 (13)	0.0615 (12)	0.0596 (11)	0.0065 (10)	0.0030 (9)	−0.0019 (9)
C6	0.0879 (15)	0.0881 (16)	0.0526 (11)	−0.0147 (13)	0.0046 (10)	−0.0034 (10)
C7	0.0646 (13)	0.122 (2)	0.0539 (11)	−0.0053 (14)	0.0001 (10)	−0.0310 (13)
C8	0.0712 (14)	0.0994 (18)	0.0800 (14)	0.0278 (13)	−0.0165 (12)	−0.0410 (14)
C9	0.0803 (14)	0.0621 (12)	0.0660 (12)	0.0053 (11)	−0.0214 (10)	−0.0076 (10)
C10	0.0371 (8)	0.0573 (10)	0.0389 (8)	−0.0030 (7)	0.0038 (6)	0.0098 (7)
C11	0.0495 (10)	0.0753 (13)	0.0483 (9)	0.0074 (9)	−0.0065 (8)	0.0056 (9)
C12	0.0561 (11)	0.0688 (12)	0.0631 (11)	0.0122 (9)	0.0009 (9)	0.0083 (9)
C13	0.0581 (10)	0.0533 (10)	0.0509 (9)	−0.0034 (8)	0.0107 (8)	0.0048 (8)
C14	0.0568 (10)	0.0665 (11)	0.0454 (8)	−0.0074 (9)	−0.0031 (8)	0.0035 (8)
C15	0.0439 (9)	0.0627 (11)	0.0468 (9)	0.0007 (8)	−0.0050 (7)	0.0048 (8)
N1	0.0337 (7)	0.0630 (9)	0.0384 (6)	0.0005 (6)	−0.0008 (5)	0.0050 (6)
N2	0.0415 (8)	0.0786 (10)	0.0547 (8)	0.0099 (7)	−0.0091 (6)	−0.0088 (8)
N3	0.0518 (9)	0.0784 (11)	0.0582 (9)	0.0064 (8)	−0.0062 (7)	−0.0122 (8)
N4	0.0873 (13)	0.0647 (11)	0.0668 (11)	−0.0013 (10)	0.0104 (10)	−0.0005 (9)
O1	0.1292 (16)	0.1118 (14)	0.1100 (13)	0.0544 (13)	−0.0054 (12)	−0.0279 (11)
O2	0.1333 (15)	0.0942 (12)	0.0817 (11)	0.0065 (11)	−0.0145 (11)	−0.0274 (9)

C1—C2	1.347 (2)	C9—H9	0.9300
C1—N3	1.362 (2)	C10—C11	1.382 (2)
C1—C3	1.499 (2)	C10—C15	1.386 (2)
C2—N1	1.3516 (19)	C10—N1	1.418 (2)
C2—H2	0.9300	C11—C12	1.375 (3)
C3—C4	1.507 (2)	C11—H11	0.9300
C3—H3A	0.9700	C12—C13	1.373 (2)
C3—H3B	0.9700	C12—H12	0.9300
C4—C9	1.371 (3)	C13—C14	1.374 (2)
C4—C5	1.377 (2)	C13—N4	1.472 (2)
C5—C6	1.371 (3)	C14—C15	1.376 (2)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.356 (3)	C15—H15	0.9300
C6—H6	0.9300	N1—N2	1.3516 (18)
C7—C8	1.360 (3)	N2—N3	1.310 (2)
C7—H7	0.9300	N4—O2	1.209 (2)
C8—C9	1.395 (3)	N4—O1	1.212 (2)
C8—H8	0.9300
C2—C1—N3	108.14 (15)	C4—C9—H9	119.8
C2—C1—C3	129.31 (16)	C8—C9—H9	119.8
N3—C1—C3	122.53 (17)	C11—C10—C15	120.48 (16)
C1—C2—N1	105.95 (14)	C11—C10—N1	119.46 (14)
C1—C2—H2	127.0	C15—C10—N1	120.06 (14)
N1—C2—H2	127.0	C12—C11—C10	120.02 (15)
C1—C3—C4	113.59 (14)	C12—C11—H11	120.0
C1—C3—H3A	108.8	C10—C11—H11	120.0
C4—C3—H3A	108.8	C13—C12—C11	118.71 (17)
C1—C3—H3B	108.8	C13—C12—H12	120.6
C4—C3—H3B	108.8	C11—C12—H12	120.6
H3A—C3—H3B	107.7	C12—C13—C14	122.19 (17)
C9—C4—C5	117.75 (18)	C12—C13—N4	118.55 (17)
C9—C4—C3	121.69 (18)	C14—C13—N4	119.26 (16)
C5—C4—C3	120.56 (17)	C13—C14—C15	119.00 (16)
C6—C5—C4	121.32 (19)	C13—C14—H14	120.5
C6—C5—H5	119.3	C15—C14—H14	120.5
C4—C5—H5	119.3	C14—C15—C10	119.57 (16)
C7—C6—C5	120.8 (2)	C14—C15—H15	120.2
C7—C6—H6	119.6	C10—C15—H15	120.2
C5—C6—H6	119.6	C2—N1—N2	109.62 (14)
C6—C7—C8	119.1 (2)	C2—N1—C10	129.48 (13)
C6—C7—H7	120.5	N2—N1—C10	120.88 (12)
C8—C7—H7	120.5	N3—N2—N1	107.26 (13)
C7—C8—C9	120.5 (2)	N2—N3—C1	109.03 (15)
C7—C8—H8	119.7	O2—N4—O1	123.3 (2)
C9—C8—H8	119.7	O2—N4—C13	118.35 (19)
C4—C9—C8	120.5 (2)	O1—N4—C13	118.30 (18)
N3—C1—C2—N1	0.06 (19)	N4—C13—C14—C15	178.33 (15)
C3—C1—C2—N1	178.62 (16)	C13—C14—C15—C10	0.3 (3)
C2—C1—C3—C4	125.1 (2)	C11—C10—C15—C14	1.0 (2)
N3—C1—C3—C4	−56.5 (2)	N1—C10—C15—C14	−178.83 (15)
C1—C3—C4—C9	108.8 (2)	C1—C2—N1—N2	−0.02 (18)
C1—C3—C4—C5	−70.5 (2)	C1—C2—N1—C10	−178.32 (15)
C9—C4—C5—C6	−1.8 (3)	C11—C10—N1—C2	−14.9 (2)
C3—C4—C5—C6	177.62 (17)	C15—C10—N1—C2	164.92 (16)
C4—C5—C6—C7	0.2 (3)	C11—C10—N1—N2	166.96 (15)
C5—C6—C7—C8	1.5 (3)	C15—C10—N1—N2	−13.2 (2)
C6—C7—C8—C9	−1.6 (3)	C2—N1—N2—N3	−0.03 (18)
C5—C4—C9—C8	1.7 (3)	C10—N1—N2—N3	178.44 (14)
C3—C4—C9—C8	−177.68 (16)	N1—N2—N3—C1	0.07 (19)
C7—C8—C9—C4	−0.1 (3)	C2—C1—N3—N2	−0.1 (2)
C15—C10—C11—C12	−1.7 (3)	C3—C1—N3—N2	−178.76 (16)
N1—C10—C11—C12	178.13 (16)	C12—C13—N4—O2	−179.00 (18)
C10—C11—C12—C13	1.0 (3)	C14—C13—N4—O2	1.6 (3)
C11—C12—C13—C14	0.3 (3)	C12—C13—N4—O1	0.4 (3)
C11—C12—C13—N4	−179.03 (16)	C14—C13—N4—O1	−178.99 (19)
C12—C13—C14—C15	−1.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···O2i	0.97	2.58	3.452 (3)	150
C3—H3A···Cg2ii	0.97	2.96	3.857 (2)	154
C8—H8···Cg1iii	0.93	2.86	3.665 (3)	146
N4—O1···Cg3iv	1.21 (1)	3.67 (1)	4.1254 (19)	103 (1)