Phenyl N-(p-tol­yl)carbamate

Bao, S.-X.; Fang, Z.; Wang, Y.-L.; Wei, P.

doi:10.1107/S1600536809022600

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1606

doi:10.1107/S1600536809022600

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Phenyl N-(p-tolyl)carbamate

Shu-Xin Bao,^a Zheng Fang,^a ^* Yong-Lu Wang ^a and Ping Wei ^b

^aSchool of Pharmaceutical Sciences, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China, and ^bCollege of Life Sciences and Pharmaceutical Engineering, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: fzcpu@163.com

(Received 11 June 2009; accepted 12 June 2009; online 17 June 2009)

The asymmetric unit of the title compound, C₁₄H₁₃NO₂, contains two crystallographically independent molecules, in which the aromatic rings are oriented at dihedral angles of 59.01 (3) and 56.98 (3)°. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules into chains.

Related literature

For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₁₃NO₂
M_r = 227.25
Triclinic, $[P \overline 1]$
a = 8.7790 (18) Å
b = 9.7470 (19) Å
c = 15.121 (3) Å
α = 87.30 (3)°
β = 77.07 (3)°
γ = 75.00 (3)°
V = 1218.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 294 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.975, T_max = 0.992
4736 measured reflections
4421 independent reflections
2781 reflections with I > 2σ(I)
R_int = 0.027
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.172
S = 1.01
4421 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3	0.86	2.13	2.972 (3)	168
N2—H2A⋯O2ⁱ	0.86	2.28	3.061 (2)	152
Symmetry code: (i) x, y+1, z.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022600/hk2710sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022600/hk2710Isup2.hkl

checkCIF report

Comment top

Some derivatives of benzoic acid are important chemical materials. We report herein the crystal structure of the title compound.

The asymmetric unit of the title compound contains two crystallographically independent molecules (Fig. 1), in which the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C2-C7), B (C9-C14) and C (C16-C21), D (C23-C28) are, of course, planar and the dihedral angles between them are A/B = 59.01 (3)° and C/D = 56.98 (3)°. Intramolecular N-H···O hydrogen bond (Table 1) links the two molecules (Fig. 1).

In the crystal structure, intermolecular N-H···O hydrogen bonds (Table 1) link the molecules into chains (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, to a cold stirring solution of p-toluidine (1.0 g) and triethylamine (0.8 ml) in methylene chloride (10 ml) was added phenyl chloroformate (1.0 ml) slowly keeping the temperature at 273 K. The mixture was then warmed and stirred for 1 h at room temperature. The mixture was washed with water (20 ml), dried over sodium sulfate, and concentrated to near dryness. The crude product was purified by recrystallization from petroleum ether (yield; 1.3 g). Crystals suitable for X-ray analysis were obtained by slow evaporation of a petroleum ether solution.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Hydrogen bond is shown as dashed line.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Phenyl N-(p-tolyl)carbamate top

Crystal data top

C₁₄H₁₃NO₂	Z = 4
M_r = 227.25	F(000) = 480
Triclinic, P1	D_x = 1.239 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7790 (18) Å	Cell parameters from 25 reflections
b = 9.7470 (19) Å	θ = 9–13°
c = 15.121 (3) Å	µ = 0.08 mm⁻¹
α = 87.30 (3)°	T = 294 K
β = 77.07 (3)°	Block, colorless
γ = 75.00 (3)°	0.30 × 0.20 × 0.10 mm
V = 1218.0 (5) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	2781 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 25.3°, θ_min = 1.4°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = −11→11
T_min = 0.975, T_max = 0.992	l = −17→18
4736 measured reflections	3 standard reflections every 120 min
4421 independent reflections	intensity decay: 1%

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)] = 0.054	H-atom parameters constrained
wR(F²) = 0.172	w = 1/[σ²(F_o²) + (0.097P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
4421 reflections	Δρ_max = 0.22 e Å⁻³
308 parameters	Δρ_min = −0.13 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.040 (5)

Crystal data top

C₁₄H₁₃NO₂	γ = 75.00 (3)°
M_r = 227.25	V = 1218.0 (5) Å³
Triclinic, P1	Z = 4
a = 8.7790 (18) Å	Mo Kα radiation
b = 9.7470 (19) Å	µ = 0.08 mm⁻¹
c = 15.121 (3) Å	T = 294 K
α = 87.30 (3)°	0.30 × 0.20 × 0.10 mm
β = 77.07 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2781 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.027
T_min = 0.975, T_max = 0.992	3 standard reflections every 120 min
4736 measured reflections	intensity decay: 1%
4421 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.172	H-atom parameters constrained
S = 1.01	Δρ_max = 0.22 e Å⁻³
4421 reflections	Δρ_min = −0.13 e Å⁻³
308 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
O1	0.2677 (3)	0.48473 (18)	0.79602 (12)	0.0801 (6)
O2	0.2281 (2)	0.27924 (16)	0.86169 (11)	0.0605 (5)
O3	0.2572 (2)	0.76205 (16)	0.89540 (11)	0.0675 (5)
O4	0.2965 (2)	0.94932 (16)	0.96266 (10)	0.0593 (5)
N1	0.2453 (3)	0.4652 (2)	0.94342 (13)	0.0641 (6)
H1A	0.2456	0.5534	0.9383	0.077*
N2	0.2903 (2)	0.96349 (19)	0.81800 (12)	0.0537 (5)
H2A	0.3101	1.0436	0.8255	0.064*
C1	0.2787 (4)	0.2204 (4)	1.2922 (2)	0.1085 (12)
H1B	0.3382	0.2673	1.3213	0.163*
H1C	0.3329	0.1212	1.2845	0.163*
H1D	0.1718	0.2311	1.3290	0.163*
C2	0.2677 (4)	0.2855 (3)	1.20065 (18)	0.0701 (8)
C3	0.3342 (3)	0.3980 (3)	1.16953 (19)	0.0750 (8)
H3A	0.3871	0.4341	1.2061	0.090*
C4	0.3240 (3)	0.4578 (3)	1.08582 (17)	0.0649 (7)
H4A	0.3684	0.5340	1.0670	0.078*
C5	0.2476 (3)	0.4040 (2)	1.02999 (16)	0.0543 (6)
C6	0.1754 (3)	0.2940 (3)	1.06131 (17)	0.0677 (7)
H6A	0.1191	0.2597	1.0259	0.081*
C7	0.1882 (4)	0.2367 (3)	1.14483 (18)	0.0728 (8)
H7A	0.1413	0.1622	1.1645	0.087*
C8	0.2428 (3)	0.3982 (2)	0.86860 (16)	0.0552 (6)
C9	0.2452 (4)	0.4455 (2)	0.71360 (17)	0.0592 (7)
C10	0.0941 (4)	0.4490 (3)	0.7028 (2)	0.0736 (8)
H10A	0.0059	0.4701	0.7518	0.088*
C11	0.0741 (5)	0.4207 (3)	0.6182 (3)	0.0944 (10)
H11A	−0.0279	0.4216	0.6098	0.113*
C12	0.2045 (6)	0.3912 (3)	0.5469 (2)	0.0998 (12)
H12A	0.1902	0.3734	0.4899	0.120*
C13	0.3554 (5)	0.3876 (3)	0.5580 (2)	0.0927 (10)
H13A	0.4439	0.3659	0.5092	0.111*
C14	0.3751 (4)	0.4166 (3)	0.6428 (2)	0.0744 (8)
H14A	0.4769	0.4164	0.6513	0.089*
C15	0.2199 (4)	0.8740 (3)	0.45921 (18)	0.0983 (11)
H15A	0.1840	0.7895	0.4568	0.148*
H15B	0.3217	0.8649	0.4171	0.148*
H15C	0.1416	0.9544	0.4434	0.148*
C16	0.2396 (3)	0.8946 (3)	0.55416 (17)	0.0683 (8)
C17	0.2895 (4)	1.0104 (3)	0.57645 (18)	0.0785 (9)
H17A	0.3120	1.0758	0.5318	0.094*
C18	0.3062 (3)	1.0305 (3)	0.66276 (17)	0.0681 (8)
H18A	0.3396	1.1090	0.6756	0.082*
C19	0.2739 (3)	0.9354 (2)	0.73064 (15)	0.0495 (6)
C20	0.2257 (4)	0.8183 (3)	0.70921 (17)	0.0675 (7)
H20A	0.2045	0.7521	0.7535	0.081*
C21	0.2095 (4)	0.8008 (3)	0.62212 (18)	0.0751 (8)
H21A	0.1769	0.7220	0.6090	0.090*
C22	0.2787 (3)	0.8796 (2)	0.89110 (15)	0.0483 (6)
C23	0.2708 (3)	0.8880 (2)	1.04888 (15)	0.0481 (6)
C24	0.3933 (3)	0.8655 (3)	1.09414 (17)	0.0587 (7)
H24A	0.4928	0.8812	1.0660	0.070*
C25	0.3663 (3)	0.8190 (3)	1.18239 (17)	0.0662 (7)
H25A	0.4482	0.8031	1.2143	0.079*
C26	0.2183 (3)	0.7959 (3)	1.22356 (17)	0.0677 (8)
H26A	0.2004	0.7656	1.2834	0.081*
C27	0.0979 (3)	0.8173 (3)	1.17687 (17)	0.0632 (7)
H27A	−0.0010	0.7998	1.2046	0.076*
C28	0.1224 (3)	0.8648 (2)	1.08853 (16)	0.0543 (6)
H28A	0.0405	0.8808	1.0566	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1460 (19)	0.0512 (11)	0.0592 (11)	−0.0492 (12)	−0.0287 (11)	0.0079 (9)
O2	0.0878 (13)	0.0380 (9)	0.0662 (11)	−0.0274 (8)	−0.0262 (9)	0.0036 (8)
O3	0.1163 (15)	0.0379 (9)	0.0578 (10)	−0.0340 (9)	−0.0233 (10)	0.0068 (8)
O4	0.0911 (13)	0.0498 (9)	0.0516 (10)	−0.0397 (9)	−0.0221 (9)	0.0072 (8)
N1	0.1033 (17)	0.0368 (10)	0.0604 (13)	−0.0304 (11)	−0.0202 (12)	0.0007 (9)
N2	0.0792 (14)	0.0374 (10)	0.0520 (11)	−0.0288 (10)	−0.0149 (10)	0.0062 (9)
C1	0.124 (3)	0.111 (3)	0.068 (2)	0.001 (2)	−0.014 (2)	0.0120 (19)
C2	0.0782 (19)	0.0606 (17)	0.0556 (16)	0.0035 (15)	−0.0058 (14)	−0.0036 (13)
C3	0.0718 (19)	0.092 (2)	0.0628 (17)	−0.0202 (16)	−0.0164 (14)	−0.0093 (16)
C4	0.0734 (18)	0.0625 (17)	0.0647 (17)	−0.0305 (14)	−0.0102 (14)	−0.0079 (13)
C5	0.0695 (16)	0.0394 (13)	0.0518 (14)	−0.0140 (11)	−0.0081 (12)	−0.0026 (11)
C6	0.098 (2)	0.0527 (15)	0.0593 (16)	−0.0330 (15)	−0.0154 (15)	−0.0012 (12)
C7	0.104 (2)	0.0464 (15)	0.0622 (17)	−0.0221 (15)	−0.0031 (16)	0.0012 (13)
C8	0.0731 (17)	0.0375 (13)	0.0597 (15)	−0.0221 (12)	−0.0157 (13)	0.0058 (11)
C9	0.085 (2)	0.0373 (13)	0.0572 (16)	−0.0205 (13)	−0.0161 (14)	0.0082 (11)
C10	0.083 (2)	0.0533 (16)	0.082 (2)	−0.0169 (15)	−0.0160 (17)	0.0110 (14)
C11	0.116 (3)	0.078 (2)	0.108 (3)	−0.034 (2)	−0.057 (2)	0.025 (2)
C12	0.178 (4)	0.068 (2)	0.067 (2)	−0.037 (2)	−0.049 (3)	0.0109 (17)
C13	0.122 (3)	0.073 (2)	0.068 (2)	−0.020 (2)	0.003 (2)	0.0026 (16)
C14	0.082 (2)	0.0612 (17)	0.078 (2)	−0.0220 (15)	−0.0114 (17)	0.0098 (15)
C15	0.145 (3)	0.087 (2)	0.0587 (18)	−0.012 (2)	−0.0344 (19)	−0.0033 (16)
C16	0.089 (2)	0.0528 (16)	0.0532 (15)	−0.0030 (14)	−0.0119 (14)	−0.0038 (12)
C17	0.118 (3)	0.0602 (17)	0.0537 (16)	−0.0259 (17)	−0.0112 (16)	0.0120 (13)
C18	0.101 (2)	0.0509 (15)	0.0568 (16)	−0.0327 (15)	−0.0123 (14)	0.0076 (12)
C19	0.0624 (15)	0.0360 (12)	0.0486 (13)	−0.0127 (11)	−0.0089 (11)	−0.0003 (10)
C20	0.108 (2)	0.0471 (14)	0.0579 (16)	−0.0333 (15)	−0.0255 (15)	0.0080 (12)
C21	0.122 (3)	0.0504 (15)	0.0629 (17)	−0.0303 (16)	−0.0309 (16)	0.0019 (13)
C22	0.0600 (15)	0.0367 (12)	0.0510 (13)	−0.0179 (11)	−0.0113 (11)	−0.0010 (10)
C23	0.0665 (16)	0.0354 (12)	0.0480 (13)	−0.0194 (11)	−0.0163 (12)	−0.0001 (10)
C24	0.0585 (16)	0.0569 (15)	0.0679 (17)	−0.0249 (12)	−0.0173 (13)	0.0042 (12)
C25	0.0712 (18)	0.0742 (18)	0.0652 (17)	−0.0273 (15)	−0.0311 (14)	0.0094 (14)
C26	0.089 (2)	0.0717 (18)	0.0483 (15)	−0.0304 (16)	−0.0177 (14)	0.0076 (13)
C27	0.0618 (17)	0.0673 (17)	0.0601 (16)	−0.0225 (13)	−0.0063 (13)	0.0052 (13)
C28	0.0555 (15)	0.0538 (14)	0.0587 (15)	−0.0194 (12)	−0.0176 (12)	0.0039 (11)

Geometric parameters (Å, º) top

O1—C8	1.366 (3)	C11—H11A	0.9300
O1—C9	1.390 (3)	C12—C13	1.363 (5)
O2—C8	1.211 (3)	C12—H12A	0.9300
O3—C22	1.205 (3)	C13—C14	1.384 (4)
O4—C22	1.363 (3)	C13—H13A	0.9300
O4—C23	1.404 (3)	C14—H14A	0.9300
N1—C5	1.415 (3)	C15—C16	1.512 (3)
N1—C8	1.340 (3)	C15—H15A	0.9600
N1—H1A	0.8600	C15—H15B	0.9600
N2—C19	1.407 (3)	C15—H15C	0.9600
N2—C22	1.345 (3)	C16—C21	1.370 (4)
N2—H2A	0.8600	C16—C17	1.392 (4)
C1—C2	1.508 (4)	C17—C18	1.374 (4)
C1—H1B	0.9600	C17—H17A	0.9300
C1—H1C	0.9600	C18—C19	1.381 (3)
C1—H1D	0.9600	C18—H18A	0.9300
C2—C7	1.378 (4)	C19—C20	1.390 (3)
C2—C3	1.387 (4)	C20—C21	1.379 (3)
C3—C4	1.380 (4)	C20—H20A	0.9300
C3—H3A	0.9300	C21—H21A	0.9300
C4—C5	1.383 (3)	C23—C24	1.366 (3)
C4—H4A	0.9300	C23—C28	1.377 (3)
C5—C6	1.395 (3)	C24—C25	1.378 (3)
C6—C7	1.372 (3)	C24—H24A	0.9300
C6—H6A	0.9300	C25—C26	1.380 (4)
C7—H7A	0.9300	C25—H25A	0.9300
C9—C14	1.357 (4)	C26—C27	1.366 (3)
C9—C10	1.364 (4)	C26—H26A	0.9300
C10—C11	1.379 (4)	C27—C28	1.382 (3)
C10—H10A	0.9300	C27—H27A	0.9300
C11—C12	1.365 (5)	C28—H28A	0.9300

C8—O1—C9	118.14 (18)	C14—C13—H13A	120.5
C22—O4—C23	118.29 (16)	C9—C14—C13	119.7 (3)
C5—N1—H1A	117.0	C9—C14—H14A	120.2
C8—N1—C5	125.91 (19)	C13—C14—H14A	120.2
C8—N1—H1A	117.0	C16—C15—H15A	109.5
C19—N2—H2A	116.2	C16—C15—H15B	109.5
C22—N2—C19	127.53 (18)	H15A—C15—H15B	109.5
C22—N2—H2A	116.2	C16—C15—H15C	109.5
C2—C1—H1B	109.5	H15A—C15—H15C	109.5
C2—C1—H1C	109.5	H15B—C15—H15C	109.5
H1B—C1—H1C	109.5	C21—C16—C17	116.9 (2)
C2—C1—H1D	109.5	C21—C16—C15	121.9 (3)
H1B—C1—H1D	109.5	C17—C16—C15	121.3 (3)
H1C—C1—H1D	109.5	C18—C17—C16	121.6 (2)
C7—C2—C3	117.1 (3)	C18—C17—H17A	119.2
C7—C2—C1	121.0 (3)	C16—C17—H17A	119.2
C3—C2—C1	121.9 (3)	C17—C18—C19	120.8 (2)
C4—C3—C2	121.9 (3)	C17—C18—H18A	119.6
C4—C3—H3A	119.1	C19—C18—H18A	119.6
C2—C3—H3A	119.1	C18—C19—C20	118.4 (2)
C3—C4—C5	119.8 (2)	C18—C19—N2	118.0 (2)
C3—C4—H4A	120.1	C20—C19—N2	123.7 (2)
C5—C4—H4A	120.1	C21—C20—C19	119.8 (2)
C4—C5—C6	119.1 (2)	C21—C20—H20A	120.1
C4—C5—N1	117.9 (2)	C19—C20—H20A	120.1
C6—C5—N1	123.0 (2)	C16—C21—C20	122.7 (3)
C7—C6—C5	119.5 (3)	C16—C21—H21A	118.7
C7—C6—H6A	120.3	C20—C21—H21A	118.7
C5—C6—H6A	120.3	O3—C22—N2	127.6 (2)
C6—C7—C2	122.5 (3)	O3—C22—O4	124.0 (2)
C6—C7—H7A	118.8	N2—C22—O4	108.47 (18)
C2—C7—H7A	118.8	C24—C23—C28	122.0 (2)
O2—C8—N1	128.3 (2)	C24—C23—O4	117.1 (2)
O2—C8—O1	123.1 (2)	C28—C23—O4	120.6 (2)
N1—C8—O1	108.56 (19)	C23—C24—C25	118.6 (2)
C14—C9—C10	121.4 (3)	C23—C24—H24A	120.7
C14—C9—O1	117.9 (3)	C25—C24—H24A	120.7
C10—C9—O1	120.4 (3)	C24—C25—C26	120.3 (2)
C9—C10—C11	119.0 (3)	C24—C25—H25A	119.9
C9—C10—H10A	120.5	C26—C25—H25A	119.9
C11—C10—H10A	120.5	C27—C26—C25	120.3 (2)
C12—C11—C10	119.8 (3)	C27—C26—H26A	119.9
C12—C11—H11A	120.1	C25—C26—H26A	119.9
C10—C11—H11A	120.1	C26—C27—C28	120.2 (2)
C13—C12—C11	121.1 (3)	C26—C27—H27A	119.9
C13—C12—H12A	119.5	C28—C27—H27A	119.9
C11—C12—H12A	119.5	C23—C28—C27	118.5 (2)
C12—C13—C14	119.0 (3)	C23—C28—H28A	120.7
C12—C13—H13A	120.5	C27—C28—H28A	120.7

C7—C2—C3—C4	−1.0 (4)	C21—C16—C17—C18	−0.7 (4)
C1—C2—C3—C4	−179.9 (3)	C15—C16—C17—C18	179.4 (3)
C2—C3—C4—C5	−0.9 (4)	C16—C17—C18—C19	0.1 (5)
C3—C4—C5—C6	2.9 (4)	C17—C18—C19—C20	0.6 (4)
C3—C4—C5—N1	−177.7 (2)	C17—C18—C19—N2	−178.8 (2)
C8—N1—C5—C4	149.9 (3)	C22—N2—C19—C18	−173.8 (2)
C8—N1—C5—C6	−30.8 (4)	C22—N2—C19—C20	6.8 (4)
C4—C5—C6—C7	−3.1 (4)	C18—C19—C20—C21	−0.8 (4)
N1—C5—C6—C7	177.6 (2)	N2—C19—C20—C21	178.6 (3)
C5—C6—C7—C2	1.2 (4)	C17—C16—C21—C20	0.5 (4)
C3—C2—C7—C6	0.8 (4)	C15—C16—C21—C20	−179.5 (3)
C1—C2—C7—C6	179.7 (3)	C19—C20—C21—C16	0.2 (5)
C5—N1—C8—O2	6.9 (4)	C19—N2—C22—O3	2.7 (4)
C5—N1—C8—O1	−170.2 (2)	C19—N2—C22—O4	−177.8 (2)
C9—O1—C8—O2	12.4 (4)	C23—O4—C22—O3	−7.4 (3)
C9—O1—C8—N1	−170.3 (2)	C23—O4—C22—N2	173.05 (18)
C8—O1—C9—C14	−116.7 (3)	C22—O4—C23—C24	124.8 (2)
C8—O1—C9—C10	69.1 (3)	C22—O4—C23—C28	−61.1 (3)
C14—C9—C10—C11	0.8 (4)	C28—C23—C24—C25	−0.4 (4)
O1—C9—C10—C11	174.8 (2)	O4—C23—C24—C25	173.5 (2)
C9—C10—C11—C12	−0.7 (4)	C23—C24—C25—C26	0.1 (4)
C10—C11—C12—C13	0.8 (5)	C24—C25—C26—C27	0.8 (4)
C11—C12—C13—C14	−1.1 (5)	C25—C26—C27—C28	−1.2 (4)
C10—C9—C14—C13	−1.1 (4)	C24—C23—C28—C27	0.0 (4)
O1—C9—C14—C13	−175.2 (2)	O4—C23—C28—C27	−173.8 (2)
C12—C13—C14—C9	1.2 (4)	C26—C27—C28—C23	0.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.86	2.13	2.972 (3)	168
N2—H2A···O2ⁱ	0.86	2.28	3.061 (2)	152

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₂
M_r	227.25
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	8.7790 (18), 9.7470 (19), 15.121 (3)
α, β, γ (°)	87.30 (3), 77.07 (3), 75.00 (3)
V (Å³)	1218.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.975, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	4736, 4421, 2781
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.172, 1.01
No. of reflections	4421
No. of parameters	308
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.13

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.86	2.13	2.972 (3)	168
N2—H2A···O2ⁱ	0.86	2.28	3.061 (2)	152

Symmetry code: (i) x, y+1, z.

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar