3-(4-Cyano­phen­yl)-N-phenyl­oxirane-2-carboxamide

He, L.

doi:10.1107/S1600536810043059

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2959

https://doi.org/10.1107/S1600536810043059

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3-(4-Cyanophenyl)-N-phenyloxirane-2-carboxamide

Long He ^a ^*

^aCollege of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: helongcwnu@yahoo.com.cn

(Received 20 October 2010; accepted 22 October 2010; online 30 October 2010)

The asymmetric unit of the crystal structure of the title compound, C₁₆H₁₂N₂O₂, contains two independent molecules. In each molecule, the two aromatic rings adopt a cis configuration about the central epoxide ring, and are oriented at dihedral angles of 61.5 (5) and 74.4 (5)°with respect to the epoxide ring in one molecule, and 60.1 (5) and 72.1 (5)° in the other one. Intermolecular classical N—H⋯O and weak C—H⋯O hydrogen bonds are present in the crystal structure.

Related literature

For the use of epoxide-containing compounds as building blocks in synthesis, see: Diez et al. (2008 ); Porter & Skidmore (2000 ); Shing et al. (2006 ); Zhu & Espenson (1995 ). For related structures, see: He (2009 ); He & Chen (2009 ).

Experimental

Crystal data

C₁₆H₁₂N₂O₂
M_r = 264.28
Monoclinic, P 2₁
a = 5.1332 (1) Å
b = 18.0803 (6) Å
c = 15.0202 (4) Å
β = 90.449 (2)°
V = 1393.98 (7) Å³
Z = 4
Cu Kα radiation
μ = 0.69 mm⁻¹
T = 293 K
0.36 × 0.34 × 0.30 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.790, T_max = 0.820
14057 measured reflections
2843 independent reflections
2534 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.083
wR(F²) = 0.178
S = 1.02
2843 reflections
322 parameters
13 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H6⋯O1ⁱ	0.90 (4)	2.21 (3)	2.960 (6)	141 (4)
N3—H22⋯O4ⁱⁱ	0.89 (3)	2.09 (3)	2.923 (5)	157 (4)
C8—H8⋯O3ⁱⁱⁱ	0.98	2.49	3.287 (8)	138
C15—H15⋯O1ⁱ	0.93	2.58	3.505 (6)	171
C24—H24⋯O2^iv	0.98	2.54	3.370 (7)	142
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z; (iii) $[-x+2, y-{\script{1\over 2}}, -z+2]$ ; (iv) $[-x+1, y+{\script{1\over 2}}, -z+2]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810043059/xu5057sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810043059/xu5057Isup2.hkl

checkCIF report

Comment top

Epoxides are particularly versatile synthetic intermediates which can readily be converted into a wide range of polyfunctional compounds (Diez et al., 2008; Porter et al., 2000; Shing et al., 2006). A useful method for the synthesis of α, β-epoxy carbonyl compounds and related compounds is the Darzens condensation (Zhu et al., 1995). We report herein the crystal structure of the title compound.

The molecular structure of (I) is shown in Fig. 1. Bond lengths and angles in (I) are normal. The asymmetric unit of the title compound consists of two crystallographically independent molecules (Fig. 1), each of which adopts a cis configuration about the epoxides ring. The dihedral angle between the C1—C6 and C10—C15 ring is 44.80 (21)° and that between C17—C22 and C26–31 phenyl ring is 47.93 (18)°. Epoxide ring O2—C8/C9 makes dihedral angles of 61.48 (35)° and 74.38 (27)° with phenyl rings C1—C6 and C10—C15, respectively. Epoxide ring O3—C24/C25 makes dihedral angles of 60.09 (36)° and 72.09 (31)° with phenyl rings C17—C22 and C26—C31, respectively. The crystal packing is stabilized by N—H···0 and C—H···0 hydrogen bonding (Table 1).

Related literature top

For the use of epoxide-containing compounds as building blocks in synthesis, see: Diez et al. (2008); Porter et al. (2000); Shing et al. (2006); Zhu et al. (1995). For related structures, see: He (2009); He & Chen (2009).

Experimental top

2-Chloro-N-phenylacetamide (0.17 g, 1.0 mmol) and potassium hydroxide (0.112 g, 2.0 mmol) were dissolved in acetonitrile (2 ml). To the solution was added 4-cyanophenylaldehyde (0.131 g, 1.0 mmol) at 298 K, the solution was stirred for 60 min and removal of solvent under reduced pressure, the residue was purified through column chromatography. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution at room temperature for 1 d.

Structure description top

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids (arbitrary spheres for H atoms).

3-(4-Cyanophenyl)-N-phenyloxirane-2-carboxamide top

Crystal data top

C₁₆H₁₂N₂O₂	F(000) = 552
M_r = 264.28	D_x = 1.259 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2yb	Cell parameters from 8634 reflections
a = 5.1332 (1) Å	θ = 2.4–72.1°
b = 18.0803 (6) Å	µ = 0.69 mm⁻¹
c = 15.0202 (4) Å	T = 293 K
β = 90.449 (2)°	Block, colorless
V = 1393.98 (7) Å³	0.36 × 0.34 × 0.30 mm
Z = 4

Data collection top

Oxford Diffraction Gemini S Ultra diffractometer	2843 independent reflections
Radiation source: fine-focus sealed tube	2534 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 15.9149 pixels mm^-1	θ_max = 73.4°, θ_min = 2.9°
ω scans	h = −4→6
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −22→21
T_min = 0.790, T_max = 0.820	l = −18→18
14057 measured reflections

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)] = 0.083	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.178	w = 1/[σ²(F_o²) + (0.019P)² + 2.850P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2843 reflections	Δρ_max = 0.23 e Å⁻³
322 parameters	Δρ_min = −0.21 e Å⁻³
13 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0029 (3)

Crystal data top

C₁₆H₁₂N₂O₂	V = 1393.98 (7) Å³
M_r = 264.28	Z = 4
Monoclinic, P2₁	Cu Kα radiation
a = 5.1332 (1) Å	µ = 0.69 mm⁻¹
b = 18.0803 (6) Å	T = 293 K
c = 15.0202 (4) Å	0.36 × 0.34 × 0.30 mm
β = 90.449 (2)°

Data collection top

Oxford Diffraction Gemini S Ultra diffractometer	2843 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	2534 reflections with I > 2σ(I)
T_min = 0.790, T_max = 0.820	R_int = 0.027
14057 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.083	13 restraints
wR(F²) = 0.178	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.23 e Å⁻³
2843 reflections	Δρ_min = −0.21 e Å⁻³
322 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
O2	0.6391 (8)	0.2940 (3)	1.1787 (3)	0.0789 (13)
O3	0.9368 (8)	0.7460 (3)	0.6402 (3)	0.0897 (15)
O4	0.4072 (7)	0.8269 (3)	0.5190 (3)	0.0903 (16)
N3	0.8436 (8)	0.8319 (3)	0.4904 (3)	0.0638 (13)
C10	0.7910 (7)	0.41180 (18)	1.1080 (2)	0.0678 (16)
C11	0.9688 (7)	0.4697 (2)	1.1039 (3)	0.086 (2)
H11	1.0993	0.4738	1.1469	0.103*
C12	0.9516 (9)	0.5213 (2)	1.0355 (3)	0.095 (2)
H12	1.0705	0.5600	1.0328	0.114*
C13	0.7566 (11)	0.5150 (2)	0.9712 (3)	0.084 (2)
C14	0.5788 (9)	0.4571 (3)	0.9753 (3)	0.090 (2)
H14	0.4483	0.4529	0.9323	0.108*
C15	0.5960 (7)	0.4055 (2)	1.0437 (3)	0.080 (2)
H15	0.4770	0.3668	1.0465	0.095*
O1	1.1682 (7)	0.2549 (3)	1.0279 (3)	0.0840 (14)
N1	0.7379 (8)	0.2356 (3)	1.0097 (3)	0.0624 (12)
C1	0.5444 (6)	0.1679 (2)	0.8919 (2)	0.0757 (19)
H1	0.4307	0.1479	0.9333	0.091*
C2	0.5285 (8)	0.1465 (2)	0.8031 (2)	0.092 (2)
H2	0.4042	0.1121	0.7851	0.111*
C3	0.6986 (9)	0.1765 (3)	0.7412 (2)	0.090 (2)
H3	0.6879	0.1621	0.6819	0.108*
C5	0.8845 (8)	0.2279 (3)	0.7681 (2)	0.106 (3)
H5	0.9982	0.2479	0.7267	0.128*
C4	0.9004 (8)	0.2493 (3)	0.8568 (3)	0.090 (2)
H4	1.0248	0.2837	0.8748	0.108*
C6	0.7304 (7)	0.2194 (2)	0.9187 (2)	0.0599 (15)
C23	0.6321 (11)	0.8126 (4)	0.5387 (4)	0.0669 (16)
C7	0.9480 (10)	0.2563 (4)	1.0554 (4)	0.0646 (15)
C9	0.8289 (13)	0.3528 (3)	1.1764 (4)	0.078 (2)
H9	0.8946	0.3695	1.2344	0.093*
C8	0.8993 (12)	0.2764 (3)	1.1510 (4)	0.0728 (18)
H8	1.0050	0.2495	1.1949	0.087*
C25	0.6995 (13)	0.7002 (3)	0.6400 (4)	0.0759 (19)
H25	0.6463	0.6826	0.6989	0.091*
C24	0.6896 (12)	0.7803 (4)	0.6287 (4)	0.077 (2)
H24	0.6255	0.8085	0.6798	0.092*
C32	0.5095 (19)	0.4971 (4)	0.3637 (5)	0.112 (3)
C31	0.7737 (7)	0.5940 (2)	0.4233 (2)	0.086 (2)
H31	0.8760	0.5939	0.3725	0.104*
C26	0.8234 (7)	0.6446 (2)	0.4910 (3)	0.0772 (19)
H26	0.9591	0.6784	0.4855	0.093*
C30	0.6705 (9)	0.6448 (3)	0.5670 (2)	0.0753 (19)
C27	0.4677 (9)	0.5943 (3)	0.5752 (3)	0.086 (2)
H27	0.3654	0.5944	0.6260	0.104*
C29	0.4180 (8)	0.5438 (3)	0.5075 (3)	0.099 (2)
H29	0.2823	0.5100	0.5130	0.118*
C28	0.5709 (9)	0.5436 (2)	0.4316 (3)	0.085 (2)
C17	0.6504 (6)	0.8529 (2)	0.3446 (2)	0.0733 (19)
H17	0.5233	0.8178	0.3569	0.088*
C22	0.8404 (7)	0.8694 (2)	0.40799 (19)	0.0563 (14)
C18	1.0305 (7)	0.9219 (2)	0.3896 (3)	0.0715 (18)
H18	1.1576	0.9329	0.4321	0.086*
C19	1.0306 (8)	0.9579 (2)	0.3079 (3)	0.089 (2)
H19	1.1578	0.9930	0.2956	0.107*
C20	0.8407 (9)	0.9414 (3)	0.2444 (2)	0.102 (3)
H20	0.8407	0.9655	0.1897	0.122*
C21	0.6506 (7)	0.8889 (3)	0.2628 (2)	0.100 (3)
H21	0.5235	0.8779	0.2204	0.120*
C16	0.736 (2)	0.5652 (4)	0.9039 (5)	0.131 (4)
N4	0.451 (2)	0.4589 (5)	0.3060 (6)	0.147 (3)
N2	0.723 (3)	0.6062 (5)	0.8458 (6)	0.184 (5)
H6	0.598 (6)	0.261 (3)	1.028 (3)	0.071 (18)*
H22	1.001 (5)	0.833 (3)	0.515 (3)	0.058 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.079 (3)	0.099 (3)	0.058 (2)	−0.004 (3)	0.0072 (19)	0.001 (2)
O3	0.084 (3)	0.123 (4)	0.062 (2)	−0.001 (3)	−0.016 (2)	0.011 (3)
O4	0.051 (2)	0.139 (4)	0.081 (3)	0.003 (3)	−0.0005 (19)	0.030 (3)
N3	0.047 (2)	0.091 (3)	0.054 (2)	0.005 (2)	−0.0022 (19)	0.010 (2)
C10	0.073 (3)	0.069 (4)	0.062 (3)	0.007 (3)	−0.001 (3)	−0.014 (3)
C11	0.080 (4)	0.085 (5)	0.094 (5)	−0.013 (4)	−0.012 (4)	−0.016 (4)
C12	0.115 (6)	0.071 (4)	0.100 (5)	−0.013 (4)	−0.003 (5)	−0.003 (4)
C13	0.106 (5)	0.070 (4)	0.078 (4)	0.008 (4)	0.008 (4)	−0.004 (3)
C14	0.128 (6)	0.066 (4)	0.075 (4)	0.016 (4)	−0.025 (4)	−0.009 (3)
C15	0.087 (4)	0.081 (4)	0.071 (4)	0.009 (4)	−0.016 (3)	−0.009 (4)
O1	0.0504 (19)	0.129 (4)	0.072 (2)	−0.011 (2)	−0.0029 (18)	−0.015 (3)
N1	0.050 (2)	0.079 (3)	0.059 (2)	0.001 (2)	0.0008 (19)	−0.005 (2)
C1	0.065 (3)	0.089 (4)	0.074 (4)	−0.011 (3)	0.004 (3)	−0.021 (4)
C2	0.095 (5)	0.100 (5)	0.083 (4)	−0.012 (4)	−0.008 (4)	−0.032 (4)
C3	0.089 (4)	0.115 (6)	0.065 (4)	−0.006 (4)	0.002 (3)	−0.020 (4)
C5	0.099 (5)	0.165 (8)	0.055 (3)	−0.029 (5)	−0.001 (3)	0.013 (5)
C4	0.079 (4)	0.128 (6)	0.062 (3)	−0.032 (4)	−0.002 (3)	0.005 (4)
C6	0.048 (2)	0.070 (4)	0.062 (3)	0.005 (3)	0.002 (2)	0.004 (3)
C23	0.058 (3)	0.078 (4)	0.066 (3)	−0.006 (3)	−0.004 (3)	0.008 (3)
C7	0.048 (3)	0.069 (3)	0.076 (3)	0.005 (3)	−0.011 (2)	0.000 (3)
C9	0.084 (4)	0.100 (5)	0.050 (3)	0.003 (4)	−0.003 (3)	−0.001 (3)
C8	0.070 (3)	0.096 (5)	0.052 (3)	0.009 (3)	−0.010 (3)	0.003 (3)
C25	0.080 (4)	0.091 (5)	0.057 (3)	−0.012 (4)	−0.001 (3)	0.019 (3)
C24	0.070 (3)	0.113 (5)	0.048 (3)	0.013 (4)	0.002 (3)	0.011 (3)
C32	0.159 (8)	0.061 (4)	0.116 (5)	−0.003 (5)	−0.014 (6)	0.004 (4)
C31	0.087 (4)	0.091 (5)	0.082 (5)	0.003 (4)	0.011 (4)	−0.001 (4)
C26	0.077 (4)	0.087 (5)	0.067 (4)	0.004 (4)	0.006 (3)	0.011 (4)
C30	0.077 (4)	0.090 (5)	0.058 (3)	0.002 (4)	−0.011 (3)	0.018 (3)
C27	0.098 (5)	0.080 (4)	0.082 (4)	−0.004 (4)	0.014 (4)	0.026 (4)
C29	0.103 (5)	0.076 (5)	0.116 (5)	−0.012 (4)	0.004 (4)	0.020 (4)
C28	0.109 (5)	0.067 (4)	0.080 (4)	0.016 (4)	−0.009 (3)	0.018 (3)
C17	0.065 (3)	0.100 (5)	0.055 (3)	−0.008 (3)	−0.004 (3)	0.000 (3)
C22	0.051 (3)	0.069 (3)	0.049 (3)	0.009 (3)	0.004 (2)	−0.001 (2)
C18	0.060 (3)	0.089 (4)	0.066 (3)	−0.005 (3)	−0.002 (3)	0.003 (3)
C19	0.071 (4)	0.105 (5)	0.091 (5)	−0.009 (4)	0.007 (3)	0.034 (4)
C20	0.081 (4)	0.160 (8)	0.066 (4)	0.022 (5)	0.009 (3)	0.039 (5)
C21	0.075 (4)	0.165 (8)	0.059 (4)	0.009 (5)	−0.015 (3)	0.020 (5)
C16	0.219 (10)	0.093 (6)	0.082 (5)	0.028 (7)	0.018 (6)	0.008 (4)
N4	0.215 (9)	0.093 (5)	0.134 (6)	−0.017 (6)	−0.018 (6)	−0.008 (4)
N2	0.358 (15)	0.095 (6)	0.100 (6)	−0.006 (9)	−0.011 (8)	0.019 (5)

Geometric parameters (Å, º) top

O2—C8	1.437 (7)	C4—H4	0.9300
O2—C9	1.442 (8)	C23—C24	1.501 (8)
O3—C24	1.421 (7)	C7—C8	1.504 (8)
O3—C25	1.473 (8)	C9—C8	1.477 (7)
O4—C23	1.218 (7)	C9—H9	0.9800
N3—C23	1.356 (7)	C8—H8	0.9800
N3—C22	1.412 (5)	C25—C24	1.459 (8)
N3—H22	0.88 (2)	C25—C30	1.493 (7)
C10—C11	1.3900	C25—H25	0.9800
C10—C15	1.3900	C24—H24	0.9800
C10—C9	1.493 (7)	C32—N4	1.147 (10)
C11—C12	1.3900	C32—C28	1.356 (7)
C11—H11	0.9300	C31—C26	1.3900
C12—C13	1.3900	C31—C28	1.3900
C12—H12	0.9300	C31—H31	0.9300
C13—C16	1.362 (7)	C26—C30	1.3900
C13—C14	1.3900	C26—H26	0.9300
C14—C15	1.3900	C30—C27	1.3900
C14—H14	0.9300	C27—C29	1.3900
C15—H15	0.9300	C27—H27	0.9300
O1—C7	1.207 (6)	C29—C28	1.3900
N1—C7	1.328 (7)	C29—H29	0.9300
N1—C6	1.398 (5)	C17—C22	1.3900
N1—H6	0.90 (3)	C17—C21	1.3900
C1—C2	1.3900	C17—H17	0.9300
C1—C6	1.3900	C22—C18	1.3900
C1—H1	0.9300	C18—C19	1.3900
C2—C3	1.3900	C18—H18	0.9300
C2—H2	0.9300	C19—C20	1.3900
C3—C5	1.3900	C19—H19	0.9300
C3—H3	0.9300	C20—C21	1.3900
C5—C4	1.3900	C20—H20	0.9300
C5—H5	0.9300	C21—H21	0.9300
C4—C6	1.3900	C16—N2	1.147 (10)

C8—O2—C9	61.7 (4)	O2—C8—C9	59.3 (4)
C24—O3—C25	60.5 (4)	O2—C8—C7	119.4 (5)
C23—N3—C22	126.1 (4)	C9—C8—C7	121.0 (5)
C23—N3—H22	121 (3)	O2—C8—H8	115.2
C22—N3—H22	111 (3)	C9—C8—H8	115.2
C11—C10—C15	120.0	C7—C8—H8	115.2
C11—C10—C9	119.1 (3)	C24—C25—O3	58.0 (4)
C15—C10—C9	120.6 (3)	C24—C25—C30	125.3 (5)
C10—C11—C12	120.0	O3—C25—C30	117.2 (5)
C10—C11—H11	120.0	C24—C25—H25	114.7
C12—C11—H11	120.0	O3—C25—H25	114.7
C13—C12—C11	120.0	C30—C25—H25	114.7
C13—C12—H12	120.0	O3—C24—C25	61.5 (4)
C11—C12—H12	120.0	O3—C24—C23	116.6 (5)
C16—C13—C14	119.2 (6)	C25—C24—C23	119.9 (6)
C16—C13—C12	120.8 (6)	O3—C24—H24	115.9
C14—C13—C12	120.0	C25—C24—H24	115.9
C15—C14—C13	120.0	C23—C24—H24	115.9
C15—C14—H14	120.0	N4—C32—C28	178.0 (11)
C13—C14—H14	120.0	C26—C31—C28	120.0
C14—C15—C10	120.0	C26—C31—H31	120.0
C14—C15—H15	120.0	C28—C31—H31	120.0
C10—C15—H15	120.0	C31—C26—C30	120.0
C7—N1—C6	125.5 (4)	C31—C26—H26	120.0
C7—N1—H6	110 (3)	C30—C26—H26	120.0
C6—N1—H6	113 (3)	C26—C30—C27	120.0
C2—C1—C6	120.0	C26—C30—C25	123.4 (4)
C2—C1—H1	120.0	C27—C30—C25	116.5 (4)
C6—C1—H1	120.0	C29—C27—C30	120.0
C1—C2—C3	120.0	C29—C27—H27	120.0
C1—C2—H2	120.0	C30—C27—H27	120.0
C3—C2—H2	120.0	C27—C29—C28	120.0
C5—C3—C2	120.0	C27—C29—H29	120.0
C5—C3—H3	120.0	C28—C29—H29	120.0
C2—C3—H3	120.0	C32—C28—C29	119.2 (5)
C3—C5—C4	120.0	C32—C28—C31	120.6 (5)
C3—C5—H5	120.0	C29—C28—C31	120.0
C4—C5—H5	120.0	C22—C17—C21	120.0
C6—C4—C5	120.0	C22—C17—H17	120.0
C6—C4—H4	120.0	C21—C17—H17	120.0
C5—C4—H4	120.0	C18—C22—C17	120.0
C4—C6—C1	120.0	C18—C22—N3	119.9 (3)
C4—C6—N1	124.0 (3)	C17—C22—N3	120.1 (3)
C1—C6—N1	116.0 (3)	C19—C18—C22	120.0
O4—C23—N3	125.2 (6)	C19—C18—H18	120.0
O4—C23—C24	118.8 (5)	C22—C18—H18	120.0
N3—C23—C24	115.4 (5)	C20—C19—C18	120.0
O1—C7—N1	125.2 (5)	C20—C19—H19	120.0
O1—C7—C8	119.7 (5)	C18—C19—H19	120.0
N1—C7—C8	114.9 (5)	C19—C20—C21	120.0
O2—C9—C8	59.0 (4)	C19—C20—H20	120.0
O2—C9—C10	117.3 (5)	C21—C20—H20	120.0
C8—C9—C10	121.4 (5)	C20—C21—C17	120.0
O2—C9—H9	115.7	C20—C21—H21	120.0
C8—C9—H9	115.7	C17—C21—H21	120.0
C10—C9—H9	115.7	N2—C16—C13	178.2 (11)

C15—C10—C11—C12	0.0	C24—O3—C25—C30	116.4 (6)
C9—C10—C11—C12	173.8 (4)	C25—O3—C24—C23	−111.2 (6)
C10—C11—C12—C13	0.0	C30—C25—C24—O3	−102.6 (7)
C11—C12—C13—C16	179.8 (6)	O3—C25—C24—C23	106.0 (6)
C11—C12—C13—C14	0.0	C30—C25—C24—C23	3.5 (10)
C16—C13—C14—C15	−179.8 (6)	O4—C23—C24—O3	163.3 (6)
C12—C13—C14—C15	0.0	N3—C23—C24—O3	−24.7 (9)
C13—C14—C15—C10	0.0	O4—C23—C24—C25	92.4 (8)
C11—C10—C15—C14	0.0	N3—C23—C24—C25	−95.6 (7)
C9—C10—C15—C14	−173.7 (4)	C28—C31—C26—C30	0.0
C6—C1—C2—C3	0.0	C31—C26—C30—C27	0.0
C1—C2—C3—C5	0.0	C31—C26—C30—C25	−175.9 (4)
C2—C3—C5—C4	0.0	C24—C25—C30—C26	54.8 (8)
C3—C5—C4—C6	0.0	O3—C25—C30—C26	−13.7 (7)
C5—C4—C6—C1	0.0	C24—C25—C30—C27	−121.2 (6)
C5—C4—C6—N1	177.7 (4)	O3—C25—C30—C27	170.3 (4)
C2—C1—C6—C4	0.0	C26—C30—C27—C29	0.0
C2—C1—C6—N1	−177.8 (4)	C25—C30—C27—C29	176.2 (4)
C7—N1—C6—C4	−27.2 (7)	C30—C27—C29—C28	0.0
C7—N1—C6—C1	150.6 (5)	N4—C32—C28—C29	66 (29)
C22—N3—C23—O4	−2.3 (10)	N4—C32—C28—C31	−110 (29)
C22—N3—C23—C24	−173.7 (5)	C27—C29—C28—C32	−175.8 (5)
C6—N1—C7—O1	−10.1 (10)	C27—C29—C28—C31	0.0
C6—N1—C7—C8	175.3 (5)	C26—C31—C28—C32	175.8 (6)
C8—O2—C9—C10	111.9 (5)	C26—C31—C28—C29	0.0
C11—C10—C9—O2	179.7 (4)	C21—C17—C22—C18	0.0
C15—C10—C9—O2	−6.5 (6)	C21—C17—C22—N3	−178.8 (4)
C11—C10—C9—C8	−111.7 (5)	C23—N3—C22—C18	142.3 (5)
C15—C10—C9—C8	62.1 (7)	C23—N3—C22—C17	−38.9 (7)
C9—O2—C8—C7	−110.7 (6)	C17—C22—C18—C19	0.0
C10—C9—C8—O2	−105.1 (6)	N3—C22—C18—C19	178.8 (4)
O2—C9—C8—C7	108.0 (6)	C22—C18—C19—C20	0.0
C10—C9—C8—C7	2.9 (9)	C18—C19—C20—C21	0.0
O1—C7—C8—O2	166.4 (6)	C19—C20—C21—C17	0.0
N1—C7—C8—O2	−18.7 (8)	C22—C17—C21—C20	0.0
O1—C7—C8—C9	96.6 (8)	C14—C13—C16—N2	−82 (44)
N1—C7—C8—C9	−88.5 (7)	C12—C13—C16—N2	98 (44)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H6···O1ⁱ	0.90 (4)	2.21 (3)	2.960 (6)	141 (4)
N3—H22···O4ⁱⁱ	0.89 (3)	2.09 (3)	2.923 (5)	157 (4)
C8—H8···O3ⁱⁱⁱ	0.98	2.49	3.287 (8)	138
C15—H15···O1ⁱ	0.93	2.58	3.505 (6)	171
C24—H24···O2^iv	0.98	2.54	3.370 (7)	142

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂N₂O₂
M_r	264.28
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	5.1332 (1), 18.0803 (6), 15.0202 (4)
β (°)	90.449 (2)
V (Å³)	1393.98 (7)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.69
Crystal size (mm)	0.36 × 0.34 × 0.30

Data collection
Diffractometer	Oxford Diffraction Gemini S Ultra
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.790, 0.820
No. of measured, independent and observed [I > 2σ(I)] reflections	14057, 2843, 2534
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.622

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.083, 0.178, 1.02
No. of reflections	2843
No. of parameters	322
No. of restraints	13
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.21

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H6···O1ⁱ	0.90 (4)	2.21 (3)	2.960 (6)	141 (4)
N3—H22···O4ⁱⁱ	0.89 (3)	2.09 (3)	2.923 (5)	157 (4)
C8—H8···O3ⁱⁱⁱ	0.98	2.49	3.287 (8)	137.9
C15—H15···O1ⁱ	0.93	2.58	3.505 (6)	170.6
C24—H24···O2^iv	0.98	2.54	3.370 (7)	141.7

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

Acknowledgements

The diffraction measurements were made at the Centre for Testing and Analysis, Sichuan University. I acknowledge financial support from China West Normal University.

References

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