4-Chloro-5-(morpholin-4-yl)-2-[(5-phenyl-1,3,4-oxa­diazol-2-yl)meth­yl]pyridazin-3(2H)-one

Sun, Y.; Wu, H.; Wei, C.; Gao, M.; Shen, Z.; Li, H.

doi:10.1107/S2414314617003704

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 3| March 2017| x170370

https://doi.org/10.1107/S2414314617003704

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4-Chloro-5-(morpholin-4-yl)-2-[(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]pyridazin-3(2H)-one

Yanwen Sun,^a Haolei Wu,^a Changheng Wei,^a Mei Gao,^a Zeyi Shen ^a and Hongsen Li ^a ^*

^aCollege of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, 333 Longteng Road, Shanghai, People's Republic of China
^*Correspondence e-mail: lihongsen19@163.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 28 February 2017; accepted 8 March 2017; online 10 March 2017)

In the title compound, C₁₇H₁₆ClN₅O₃, the phenyl and the oxadiazole rings are almost coplanar, subtending a dihedral angle of 4.34 (19)°. These rings lie almost normal to the pyridazine ring, making dihedral angles of 87.35 (16) and 89.06 (15)°, respectively. The morpholine ring has the usual chair conformation and its mean plane is inclined to the pyridazine ring by 39.45 (17)°. There is a short intramolecular C—H⋯Cl contact present. In the crystal, molecules are linked by bifurcated C—(H,H)⋯O hydrogen bonds and a C—H⋯N hydrogen bond, forming layers parallel to the ab plane.

Keywords: crystal structure; 1,3,4-oxadiazole; pyridazin-3-one; morpholino; hydrogen bonding.

CCDC reference: 1536569

Structure description

1,3,4-Oxadiazole derivatives are a promising field of study because they possess good bioactivity (Liu et al., 2014 ). This substructural unit has been used as a scaffold to design and synthesize chemical compounds with biological, medicinal and agricultural activities (Gan et al., 2016 ; Shaikh & Meshram, 2016 ; Luqman et al., 2015 ; Fershtat et al. 2016 ; Pattison et al., 2009 ). A series of oxadiazoles containing a pyridazinone ring have been designed and synthesized, and we report herein on the crystal structure of one such compound.

The molecular structure of the title compound is shown in Fig. 1. The phenyl (C1–C6) and the oxadiazole (O1/N1/N2/C7/C8) rings are almost coplanar, subtending a dihedral angle of 4.34 (19)°. These rings lie almost normal to the pyridazine (N3/N4/C10–C13) ring, making dihedral angles of 87.35 (16) and 89.06 (15)°, respectively. The morpholine (O3/N5/C14–C17) ring has a chair conformation and its mean plane is inclined to the pyridazine ring by 39.45 (17)°. There is a short intramolecular C—H⋯Cl contact present (Table 1, Fig. 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯Cl1	0.97	2.57	3.252 (3)	127
C14—H14B⋯O2ⁱ	0.97	2.57	3.373 (4)	141
C13—H13⋯O2ⁱⁱ	0.93	2.60	3.507 (3)	165
C9—H9A⋯N2ⁱⁱⁱ	0.97	2.50	3.310 (4)	141
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) x-1, y, z.

Figure 1
The molecular structure of the title compound, with the atom labelling and displacement ellipsoids drawn at the 50% probability level.

In the crystal, molecules are linked by bifurcated C—(H,H)⋯O hydrogen bonds and C—H⋯·N hydrogen bond bonds, forming layers parallel to the ab plane (Table 1 and Fig. 2).

Figure 2
A view along the c axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1

Synthesis and crystallization

To a three-necked flask, 4,5-dichloro-2-((5- phenyl-1,3,4-oxadiazol-2-yl)methyl)-pyridazin-3-(2H)-one (3.0 g, 9.3 mmol; Li et al., 2005 ) and morpholine (14.0 mmol, 1.22 g) were added and reacted at 333 K for 8 h in the presence of potassium carbonate (2 g) and 20 ml dry DMF. The reaction was monitored by TLC. On completion of the reaction, the mixture was poured into ice–water. The precipitate formed was collected by filtration, dried to give the pure title compound (yield 2.23 g, 64.2%). It was recrystallized from chloroform, ethyl acetate and petroleum (2:2:5) to give pale-yellow prismatic crystals (m.p. 461–463 K).

¹H NMR (CDCl₃): 3.47 (t, 4H), 3.86 (t, 4H), 5.64 (s, 2H), 7.53 (m, 3H), 7.68 (s, 1H), 8.06 (m, 2H). IR (KBr, cm⁻¹) ν 2957, 2857, 1641, 1593, 1549, 1487, 1446, 1423, 1257, 1117, 780.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₁₆ClN₅O₃
M_r	373.80
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	4.7931 (7), 10.4177 (15), 33.685 (5)
V (Å³)	1682.0 (4)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.26
Crystal size (mm)	0.20 × 0.16 × 0.11

Data collection
Diffractometer	Bruker SMART CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2008 )
T_min, T_max	0.658, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	10022, 3282, 2995
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.096, 1.07
No. of reflections	3282
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.17
Absolute structure	Flack x determined using 1105 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.05 (3)
Computer programs: SMART and SAINT (Bruker, 2008), SHELXS97 and SHELXTL (Sheldrick, 2008 ), SHELXL2013 (Sheldrick, 2015 ), Mercury (Macrae et al., 2008 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1536569

Crystal structure: contains datablocks I, Global. DOI: https://doi.org/10.1107/S2414314617003704/su4138sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617003704/su4138Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617003704/su4138Isup3.cml

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

4-Chloro-5-(morpholin-4-yl)-2-[(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]pyridazin-3(2H)-one top

Crystal data top

C₁₇H₁₆ClN₅O₃	D_x = 1.476 Mg m⁻³
M_r = 373.80	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 3057 reflections
a = 4.7931 (7) Å	θ = 4.6–50.4°
b = 10.4177 (15) Å	µ = 0.26 mm⁻¹
c = 33.685 (5) Å	T = 293 K
V = 1682.0 (4) Å³	Prismatic, pale-yellow
Z = 4	0.20 × 0.16 × 0.11 mm
F(000) = 776

Data collection top

Bruker SMART CCD area detector diffractometer	2995 reflections with I > 2σ(I)
phi and ω scans	R_int = 0.036
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θ_max = 26.0°, θ_min = 2.1°
T_min = 0.658, T_max = 0.746	h = −5→5
10022 measured reflections	k = −12→12
3282 independent reflections	l = −40→41

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0555P)²] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.002
3282 reflections	Δρ_max = 0.21 e Å⁻³
235 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Absolute structure: Flack x determined using 1105 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (3)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.59088 (15)	−0.01685 (6)	0.76733 (2)	0.0433 (2)
N1	0.4856 (6)	0.2459 (3)	0.59442 (7)	0.0529 (7)
N2	0.3286 (6)	0.2745 (3)	0.62853 (7)	0.0486 (7)
N3	0.0445 (5)	0.1687 (2)	0.70294 (7)	0.0368 (5)
N4	−0.0777 (6)	0.2543 (2)	0.72725 (7)	0.0396 (5)
N5	0.2681 (5)	0.1739 (2)	0.82072 (7)	0.0405 (6)
O1	0.1658 (5)	0.09679 (19)	0.60219 (6)	0.0451 (5)
O2	0.3400 (4)	0.00730 (18)	0.68817 (6)	0.0452 (5)
O3	0.2610 (7)	0.1845 (3)	0.90460 (7)	0.0765 (9)
C1	0.3377 (8)	−0.0400 (4)	0.53314 (10)	0.0608 (10)
H1	0.2004	−0.0757	0.5492	0.073*
C2	0.4134 (11)	−0.1013 (4)	0.49869 (11)	0.0736 (11)
H2	0.3278	−0.1779	0.4914	0.088*
C3	0.6176 (10)	−0.0483 (4)	0.47491 (11)	0.0722 (11)
H3	0.6687	−0.0890	0.4514	0.087*
C4	0.7437 (9)	0.0626 (4)	0.48555 (10)	0.0690 (11)
H4	0.8819	0.0972	0.4694	0.083*
C5	0.6695 (8)	0.1252 (4)	0.52024 (10)	0.0581 (9)
H5	0.7578	0.2012	0.5274	0.070*
C6	0.4629 (7)	0.0738 (3)	0.54413 (8)	0.0462 (8)
C7	0.3820 (7)	0.1421 (3)	0.57997 (8)	0.0430 (7)
C8	0.1487 (7)	0.1844 (3)	0.63175 (8)	0.0400 (7)
C9	−0.0686 (7)	0.1662 (3)	0.66278 (8)	0.0421 (7)
H9A	−0.2075	0.2334	0.6602	0.050*
H9B	−0.1610	0.0845	0.6584	0.050*
C10	0.2450 (6)	0.0805 (3)	0.71332 (8)	0.0342 (6)
C11	0.3255 (5)	0.0852 (2)	0.75441 (8)	0.0316 (6)
C12	0.2033 (6)	0.1676 (2)	0.78069 (8)	0.0334 (6)
C13	−0.0014 (6)	0.2522 (2)	0.76394 (8)	0.0378 (7)
H13	−0.0863	0.3106	0.7810	0.045*
C14	0.1841 (9)	0.2897 (3)	0.84206 (9)	0.0505 (9)
H14A	−0.0167	0.2901	0.8456	0.061*
H14B	0.2352	0.3650	0.8268	0.061*
C15	0.3242 (10)	0.2938 (4)	0.88161 (10)	0.0663 (11)
H15A	0.5245	0.2991	0.8778	0.080*
H15B	0.2650	0.3702	0.8958	0.080*
C16	0.3517 (11)	0.0713 (4)	0.88451 (10)	0.0739 (12)
H16A	0.3067	−0.0032	0.9005	0.089*
H16B	0.5528	0.0742	0.8814	0.089*
C17	0.2186 (9)	0.0577 (3)	0.84467 (9)	0.0538 (9)
H17A	0.2956	−0.0165	0.8311	0.065*
H17B	0.0196	0.0444	0.8478	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0348 (4)	0.0369 (4)	0.0584 (4)	0.0064 (3)	0.0008 (3)	0.0035 (3)
N1	0.0579 (19)	0.0594 (17)	0.0416 (14)	−0.0151 (15)	0.0007 (13)	0.0019 (12)
N2	0.0553 (17)	0.0510 (14)	0.0395 (14)	−0.0093 (14)	−0.0015 (12)	0.0000 (11)
N3	0.0351 (13)	0.0353 (12)	0.0399 (12)	0.0023 (11)	0.0019 (10)	0.0019 (10)
N4	0.0379 (13)	0.0357 (12)	0.0451 (14)	0.0058 (11)	0.0071 (12)	0.0019 (10)
N5	0.0495 (15)	0.0341 (13)	0.0379 (13)	−0.0002 (12)	0.0075 (11)	0.0012 (10)
O1	0.0496 (13)	0.0460 (11)	0.0396 (11)	−0.0079 (11)	0.0004 (9)	−0.0011 (9)
O2	0.0496 (13)	0.0407 (11)	0.0455 (11)	0.0067 (11)	0.0072 (9)	−0.0061 (9)
O3	0.108 (2)	0.0816 (18)	0.0397 (13)	0.0122 (19)	0.0130 (14)	0.0015 (12)
C1	0.062 (2)	0.072 (2)	0.0486 (19)	−0.007 (2)	0.0062 (17)	−0.0053 (17)
C2	0.081 (3)	0.078 (3)	0.062 (2)	−0.004 (3)	0.000 (2)	−0.019 (2)
C3	0.077 (3)	0.094 (3)	0.046 (2)	0.007 (3)	0.005 (2)	−0.0082 (19)
C4	0.074 (3)	0.085 (3)	0.048 (2)	0.004 (2)	0.0156 (19)	0.0109 (19)
C5	0.067 (2)	0.062 (2)	0.0454 (19)	−0.0025 (19)	0.0026 (17)	0.0083 (15)
C6	0.0483 (19)	0.0574 (18)	0.0329 (15)	0.0057 (16)	−0.0071 (13)	0.0068 (13)
C7	0.0435 (17)	0.0503 (17)	0.0352 (14)	−0.0045 (15)	−0.0040 (13)	0.0107 (13)
C8	0.0439 (18)	0.0416 (15)	0.0345 (14)	0.0000 (14)	−0.0076 (13)	0.0044 (12)
C9	0.0376 (16)	0.0464 (16)	0.0422 (16)	0.0002 (15)	−0.0043 (14)	0.0006 (12)
C10	0.0294 (14)	0.0295 (13)	0.0438 (15)	−0.0030 (12)	0.0085 (12)	−0.0009 (12)
C11	0.0269 (13)	0.0256 (13)	0.0423 (15)	−0.0021 (11)	0.0031 (11)	0.0022 (11)
C12	0.0333 (14)	0.0265 (13)	0.0405 (14)	−0.0049 (12)	0.0063 (12)	0.0014 (11)
C13	0.0398 (16)	0.0288 (13)	0.0448 (16)	0.0040 (12)	0.0096 (13)	−0.0009 (12)
C14	0.066 (2)	0.0415 (16)	0.0437 (17)	−0.0024 (16)	0.0098 (16)	−0.0045 (13)
C15	0.080 (3)	0.068 (2)	0.0501 (19)	−0.006 (2)	0.0091 (19)	−0.0116 (17)
C16	0.100 (4)	0.075 (2)	0.0470 (19)	0.025 (3)	0.008 (2)	0.0126 (17)
C17	0.073 (2)	0.0413 (16)	0.0475 (18)	0.0036 (17)	0.0125 (17)	0.0095 (14)

Geometric parameters (Å, º) top

Cl1—C11	1.714 (3)	C4—C5	1.385 (5)
N1—C7	1.285 (4)	C4—H4	0.9300
N1—N2	1.405 (4)	C5—C6	1.384 (5)
N2—C8	1.278 (4)	C5—H5	0.9300
N3—N4	1.345 (3)	C6—C7	1.454 (4)
N3—C10	1.375 (4)	C8—C9	1.488 (4)
N3—C9	1.457 (4)	C9—H9A	0.9700
N4—C13	1.289 (4)	C9—H9B	0.9700
N5—C12	1.385 (4)	C10—C11	1.438 (4)
N5—C14	1.461 (4)	C11—C12	1.365 (4)
N5—C17	1.474 (4)	C12—C13	1.435 (4)
O1—C8	1.354 (3)	C13—H13	0.9300
O1—C7	1.363 (4)	C14—C15	1.493 (5)
O2—C10	1.228 (3)	C14—H14A	0.9700
O3—C15	1.411 (4)	C14—H14B	0.9700
O3—C16	1.427 (4)	C15—H15A	0.9700
C1—C2	1.373 (5)	C15—H15B	0.9700
C1—C6	1.380 (5)	C16—C17	1.493 (5)
C1—H1	0.9300	C16—H16A	0.9700
C2—C3	1.380 (6)	C16—H16B	0.9700
C2—H2	0.9300	C17—H17A	0.9700
C3—C4	1.351 (6)	C17—H17B	0.9700
C3—H3	0.9300

C7—N1—N2	106.3 (3)	C8—C9—H9B	109.0
C8—N2—N1	106.0 (2)	H9A—C9—H9B	107.8
N4—N3—C10	126.3 (2)	O2—C10—N3	119.9 (3)
N4—N3—C9	114.5 (2)	O2—C10—C11	125.9 (3)
C10—N3—C9	119.0 (2)	N3—C10—C11	114.2 (2)
C13—N4—N3	116.7 (2)	C12—C11—C10	122.0 (3)
C12—N5—C14	117.1 (2)	C12—C11—Cl1	122.9 (2)
C12—N5—C17	117.2 (2)	C10—C11—Cl1	115.0 (2)
C14—N5—C17	111.4 (2)	C11—C12—N5	124.4 (3)
C8—O1—C7	102.5 (2)	C11—C12—C13	115.1 (2)
C15—O3—C16	110.0 (3)	N5—C12—C13	120.5 (2)
C2—C1—C6	120.8 (4)	N4—C13—C12	125.5 (2)
C2—C1—H1	119.6	N4—C13—H13	117.2
C6—C1—H1	119.6	C12—C13—H13	117.2
C1—C2—C3	119.5 (4)	N5—C14—C15	109.8 (3)
C1—C2—H2	120.3	N5—C14—H14A	109.7
C3—C2—H2	120.3	C15—C14—H14A	109.7
C4—C3—C2	120.4 (4)	N5—C14—H14B	109.7
C4—C3—H3	119.8	C15—C14—H14B	109.7
C2—C3—H3	119.8	H14A—C14—H14B	108.2
C3—C4—C5	120.8 (4)	O3—C15—C14	111.7 (3)
C3—C4—H4	119.6	O3—C15—H15A	109.3
C5—C4—H4	119.6	C14—C15—H15A	109.3
C6—C5—C4	119.5 (4)	O3—C15—H15B	109.3
C6—C5—H5	120.3	C14—C15—H15B	109.3
C4—C5—H5	120.3	H15A—C15—H15B	107.9
C1—C6—C5	119.2 (3)	O3—C16—C17	112.0 (3)
C1—C6—C7	121.8 (3)	O3—C16—H16A	109.2
C5—C6—C7	119.0 (3)	C17—C16—H16A	109.2
N1—C7—O1	112.2 (3)	O3—C16—H16B	109.2
N1—C7—C6	128.5 (3)	C17—C16—H16B	109.2
O1—C7—C6	119.3 (3)	H16A—C16—H16B	107.9
N2—C8—O1	113.1 (3)	N5—C17—C16	110.2 (3)
N2—C8—C9	128.7 (3)	N5—C17—H17A	109.6
O1—C8—C9	118.2 (3)	C16—C17—H17A	109.6
N3—C9—C8	112.9 (3)	N5—C17—H17B	109.6
N3—C9—H9A	109.0	C16—C17—H17B	109.6
C8—C9—H9A	109.0	H17A—C17—H17B	108.1
N3—C9—H9B	109.0

C7—N1—N2—C8	1.0 (3)	N4—N3—C10—O2	179.9 (3)
C10—N3—N4—C13	−0.9 (4)	C9—N3—C10—O2	5.1 (4)
C9—N3—N4—C13	174.2 (3)	N4—N3—C10—C11	−0.5 (4)
C6—C1—C2—C3	0.1 (6)	C9—N3—C10—C11	−175.3 (2)
C1—C2—C3—C4	0.5 (7)	O2—C10—C11—C12	−178.2 (3)
C2—C3—C4—C5	−0.4 (6)	N3—C10—C11—C12	2.3 (4)
C3—C4—C5—C6	−0.3 (6)	O2—C10—C11—Cl1	3.5 (4)
C2—C1—C6—C5	−0.8 (5)	N3—C10—C11—Cl1	−176.01 (19)
C2—C1—C6—C7	178.6 (4)	C10—C11—C12—N5	178.4 (2)
C4—C5—C6—C1	0.9 (5)	Cl1—C11—C12—N5	−3.4 (4)
C4—C5—C6—C7	−178.5 (3)	C10—C11—C12—C13	−2.5 (4)
N2—N1—C7—O1	−0.7 (3)	Cl1—C11—C12—C13	175.65 (19)
N2—N1—C7—C6	178.0 (3)	C14—N5—C12—C11	162.1 (3)
C8—O1—C7—N1	0.1 (3)	C17—N5—C12—C11	−61.4 (4)
C8—O1—C7—C6	−178.7 (3)	C14—N5—C12—C13	−16.9 (4)
C1—C6—C7—N1	177.5 (3)	C17—N5—C12—C13	119.5 (3)
C5—C6—C7—N1	−3.1 (5)	N3—N4—C13—C12	0.6 (4)
C1—C6—C7—O1	−3.9 (5)	C11—C12—C13—N4	1.0 (4)
C5—C6—C7—O1	175.5 (3)	N5—C12—C13—N4	−179.8 (3)
N1—N2—C8—O1	−1.0 (3)	C12—N5—C14—C15	−167.2 (3)
N1—N2—C8—C9	179.3 (3)	C17—N5—C14—C15	53.9 (4)
C7—O1—C8—N2	0.6 (3)	C16—O3—C15—C14	60.0 (5)
C7—O1—C8—C9	−179.7 (2)	N5—C14—C15—O3	−58.0 (4)
N4—N3—C9—C8	125.5 (3)	C15—O3—C16—C17	−58.7 (5)
C10—N3—C9—C8	−59.1 (3)	C12—N5—C17—C16	168.4 (3)
N2—C8—C9—N3	−53.4 (4)	C14—N5—C17—C16	−52.8 (4)
O1—C8—C9—N3	127.0 (3)	O3—C16—C17—N5	55.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···Cl1	0.97	2.57	3.252 (3)	127
C14—H14B···O2ⁱ	0.97	2.57	3.373 (4)	141
C13—H13···O2ⁱⁱ	0.93	2.60	3.507 (3)	165
C9—H9A···N2ⁱⁱⁱ	0.97	2.50	3.310 (4)	141

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

Funding information

Funding for this research was provided by: Shanghai Municipal Education Commission of China; Shanghai University of Engineering Science (award No. 1–5300-16–020113).

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