Phenyl N-(4-methoxy­phen­yl)carbamate

Fang, Z.; Wang, Y.-L.; Ren, L.-L.; Wei, P.

doi:10.1107/S1600536809028785

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1997

doi:10.1107/S1600536809028785

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Phenyl N-(4-methoxyphenyl)carbamate

Zheng Fang,^a ^* Yong-Lu Wang,^a Li-Li Ren ^a and Ping Wei ^b

^aSchool of Pharmaceutical Sciences, Nanjing University of Technology, Nanjing 210009, People's Republic of China, and ^bSchool of Biotechnology and Pharmaceutical Engineering, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: fzcpu@163.com

(Received 18 July 2009; accepted 21 July 2009; online 25 July 2009)

The asymmetric unit of the title compound, C₁₄H₁₃NO₃, contains two crystallographically independent molecules, in which the aromatic rings are oriented at dihedral angles of 75.64 (3) and 83.14 (3)°. An N—H⋯O hydrogen bond links the two molecules. Weak intramolecular C—H⋯O interactions are observed in the two molecules. In the crystal structure, intermolecular N—H⋯O and C—H⋯O interactions link the molecules into a two-dimensional network.

Related literature

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

Experimental

Crystal data

C₁₄H₁₃NO₃
M_r = 243.25
Monoclinic, P 2₁ /n
a = 9.869 (2) Å
b = 10.870 (2) Å
c = 23.319 (5) Å
β = 100.27 (3)°
V = 2461.5 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.09 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 = 0.973, T_max = 0.991
4733 measured reflections
4459 independent reflections
2109 reflections with I > 2σ(I)
R_int = 0.045
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.184
S = 1.03
4459 reflections
319 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O5	0.86	2.19	3.038 (4)	170
N2—H2B⋯O2ⁱ	0.86	2.22	3.062 (4)	166
C6—H6A⋯O5ⁱⁱ	0.93	2.58	3.435 (5)	153
C9—H9A⋯O2	0.93	2.52	2.967 (5)	110
C23—H23A⋯O2ⁱ	0.93	2.60	3.390 (4)	144
C27—H27A⋯O5	0.93	2.30	2.907 (5)	122
Symmetry codes: (i) x+1, y, z; (ii) -x+2, -y+2, -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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809028785/hk2744sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028785/hk2744Isup2.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 (C1-C6), B (C8-C13) and C (C15-C20), D (C22-C27) are, of course, planar and they are oriented at dihedral angles of A/B = 75.64 (3) and C/D = 83.14 (3)°. Intramolecular N-H···O hydrogen bond (Table 1) link the two molecules (Fig. 1). There also exist two intramolecular C-H···O interactions (Table 1).

In the crystal structure, intramolecular N-H···O and intermolecular N-H···O and C-H···O interactions (Table 1) link the molecules into a two dimensional network (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 4-methoxybenzenamine (1.0 g) and triethylamine (0.8 ml) in methylene chloride (10 ml) was added phenyl chloroformate (1.0 ml) slowly 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).

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-(4-methoxyphenyl)carbamate top

Crystal data top

C₁₄H₁₃NO₃	F(000) = 1024
M_r = 243.25	D_x = 1.313 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 9.869 (2) Å	θ = 10–13°
b = 10.870 (2) Å	µ = 0.09 mm⁻¹
c = 23.319 (5) Å	T = 294 K
β = 100.27 (3)°	Block, colorless
V = 2461.5 (9) Å³	0.30 × 0.20 × 0.10 mm
Z = 8

Data collection top

Enraf–Nonius CAD-4 diffractometer	2109 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.045
Graphite monochromator	θ_max = 25.3°, θ_min = 1.8°
ω/2θ scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = 0→13
T_min = 0.973, T_max = 0.991	l = −28→27
4733 measured reflections	3 standard reflections every 120 min
4459 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.184	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.08P)²] where P = (F_o² + 2F_c²)/3
4459 reflections	(Δ/σ)_max < 0.001
319 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₄H₁₃NO₃	V = 2461.5 (9) Å³
M_r = 243.25	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.869 (2) Å	µ = 0.09 mm⁻¹
b = 10.870 (2) Å	T = 294 K
c = 23.319 (5) Å	0.30 × 0.20 × 0.10 mm
β = 100.27 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2109 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.045
T_min = 0.973, T_max = 0.991	3 standard reflections every 120 min
4733 measured reflections	intensity decay: 1%
4459 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.184	H-atom parameters constrained
S = 1.03	Δρ_max = 0.43 e Å⁻³
4459 reflections	Δρ_min = −0.34 e Å⁻³
319 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	1.0212 (2)	0.7911 (3)	0.03978 (13)	0.0894 (8)
O2	0.8011 (2)	0.7329 (2)	0.01287 (11)	0.0730 (8)
O3	0.6882 (3)	0.3624 (3)	−0.20767 (12)	0.0811 (8)
O4	1.4527 (2)	0.6417 (3)	−0.07369 (12)	0.0818 (9)
O5	1.2693 (2)	0.7162 (2)	−0.03922 (11)	0.0731 (8)
O6	1.4470 (2)	1.1216 (2)	0.16973 (11)	0.0725 (8)
N1	0.9696 (3)	0.6635 (3)	−0.03360 (15)	0.0730 (9)
H1A	1.0567	0.6696	−0.0331	0.088*
N2	1.4897 (3)	0.7712 (3)	−0.00016 (13)	0.0618 (8)
H2B	1.5736	0.7542	−0.0026	0.074*
C1	0.9618 (5)	1.0279 (5)	0.1698 (3)	0.1066 (17)
H1B	0.9538	1.0851	0.1986	0.128*
C2	1.0165 (5)	0.9067 (6)	0.1852 (2)	0.1185 (18)
H2A	1.0409	0.8824	0.2239	0.142*
C3	1.0310 (4)	0.8289 (5)	0.1404 (2)	0.0975 (15)
H3A	1.0668	0.7505	0.1486	0.117*
C4	0.9940 (3)	0.8648 (4)	0.08460 (18)	0.0628 (10)
C5	0.9390 (4)	0.9807 (4)	0.07198 (19)	0.0745 (11)
H5A	0.9125	1.0061	0.0335	0.089*
C6	0.9246 (4)	1.0556 (5)	0.1160 (2)	0.0919 (14)
H6A	0.8851	1.1325	0.1069	0.110*
C7	0.9180 (4)	0.7285 (4)	0.0059 (2)	0.0894 (8)
C8	0.8940 (4)	0.5852 (3)	−0.07637 (18)	0.0628 (10)
C9	0.7833 (4)	0.5173 (4)	−0.06612 (18)	0.0689 (11)
H9A	0.7568	0.5211	−0.0298	0.083*
C10	0.7113 (4)	0.4439 (4)	−0.10902 (17)	0.0684 (11)
H10A	0.6362	0.3990	−0.1016	0.082*
C11	0.7492 (4)	0.4364 (4)	−0.16274 (18)	0.0627 (10)
C12	0.8617 (4)	0.5036 (4)	−0.17297 (18)	0.0724 (11)
H12A	0.8891	0.4986	−0.2090	0.087*
C13	0.9328 (4)	0.5771 (4)	−0.13035 (19)	0.0736 (11)
H13A	1.0079	0.6221	−0.1378	0.088*
C14	0.5858 (5)	0.2793 (4)	−0.1969 (2)	0.0984 (15)
H14A	0.5518	0.2336	−0.2317	0.148*
H14B	0.5115	0.3242	−0.1852	0.148*
H14C	0.6245	0.2236	−0.1664	0.148*
C15	1.2046 (4)	0.4562 (5)	−0.2066 (2)	0.0894 (14)
H15A	1.1504	0.4138	−0.2370	0.107*
C16	1.2464 (5)	0.5728 (5)	−0.2151 (2)	0.0938 (14)
H16A	1.2203	0.6100	−0.2513	0.113*
C17	1.3267 (4)	0.6362 (4)	−0.17070 (19)	0.0764 (12)
H17A	1.3553	0.7160	−0.1765	0.092*
C18	1.3637 (3)	0.5799 (4)	−0.11805 (17)	0.0645 (11)
C19	1.3217 (4)	0.4635 (4)	−0.1092 (2)	0.0778 (12)
H19A	1.3471	0.4261	−0.0730	0.093*
C20	1.2418 (5)	0.4019 (4)	−0.1541 (3)	0.0903 (14)
H20A	1.2130	0.3220	−0.1484	0.108*
C21	1.3919 (4)	0.7121 (3)	−0.03685 (16)	0.0584 (10)
C22	1.4700 (3)	0.8590 (3)	0.04237 (15)	0.0526 (9)
C23	1.5852 (3)	0.9022 (4)	0.07914 (16)	0.0629 (10)
H23A	1.6716	0.8719	0.0758	0.075*
C24	1.5739 (4)	0.9892 (4)	0.12045 (17)	0.0661 (11)
H24A	1.6528	1.0165	0.1451	0.079*
C25	1.4473 (3)	1.0370 (3)	0.12614 (15)	0.0554 (9)
C26	1.3334 (3)	0.9931 (4)	0.09065 (16)	0.0646 (10)
H26A	1.2471	1.0230	0.0944	0.078*
C27	1.3439 (3)	0.9049 (4)	0.04911 (17)	0.0688 (11)
H27A	1.2645	0.8760	0.0253	0.083*
C28	1.3265 (4)	1.1931 (4)	0.16771 (19)	0.0853 (13)
H28A	1.3391	1.2493	0.2000	0.128*
H28B	1.2499	1.1400	0.1699	0.128*
H28C	1.3089	1.2386	0.1319	0.128*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0469 (13)	0.107 (2)	0.118 (2)	−0.0070 (13)	0.0267 (13)	−0.0378 (17)
O2	0.0419 (13)	0.0875 (19)	0.092 (2)	0.0005 (13)	0.0174 (12)	−0.0078 (15)
O3	0.085 (2)	0.085 (2)	0.0725 (19)	−0.0031 (17)	0.0130 (15)	0.0021 (17)
O4	0.0475 (14)	0.114 (2)	0.0847 (19)	−0.0007 (15)	0.0136 (14)	−0.0360 (18)
O5	0.0390 (14)	0.095 (2)	0.0863 (19)	−0.0060 (14)	0.0130 (12)	−0.0183 (16)
O6	0.0538 (15)	0.0753 (18)	0.0846 (19)	0.0041 (14)	0.0023 (13)	−0.0187 (16)
N1	0.0414 (16)	0.081 (2)	0.100 (2)	−0.0004 (17)	0.0213 (17)	−0.009 (2)
N2	0.0363 (14)	0.088 (2)	0.0609 (18)	0.0009 (16)	0.0069 (13)	−0.0087 (18)
C1	0.072 (3)	0.141 (4)	0.104 (4)	−0.021 (3)	0.009 (3)	−0.049 (4)
C2	0.098 (4)	0.176 (5)	0.076 (3)	0.010 (4)	−0.001 (3)	0.023 (3)
C3	0.083 (3)	0.107 (4)	0.101 (3)	0.033 (3)	0.012 (3)	0.033 (3)
C4	0.0358 (18)	0.075 (3)	0.077 (3)	−0.0032 (19)	0.0079 (18)	−0.004 (2)
C5	0.058 (2)	0.097 (3)	0.069 (3)	0.009 (2)	0.014 (2)	0.018 (2)
C6	0.074 (3)	0.083 (3)	0.119 (4)	−0.010 (3)	0.018 (3)	−0.008 (3)
C7	0.0469 (13)	0.107 (2)	0.118 (2)	−0.0070 (13)	0.0267 (13)	−0.0378 (17)
C8	0.046 (2)	0.059 (2)	0.087 (3)	0.0060 (19)	0.019 (2)	0.002 (2)
C9	0.058 (2)	0.079 (3)	0.073 (3)	−0.001 (2)	0.023 (2)	0.005 (2)
C10	0.057 (2)	0.081 (3)	0.072 (3)	−0.005 (2)	0.022 (2)	0.007 (2)
C11	0.059 (2)	0.057 (2)	0.073 (3)	0.008 (2)	0.011 (2)	0.006 (2)
C12	0.074 (3)	0.066 (3)	0.084 (3)	0.004 (2)	0.035 (2)	−0.002 (2)
C13	0.061 (2)	0.069 (3)	0.100 (3)	−0.003 (2)	0.039 (2)	−0.001 (3)
C14	0.091 (3)	0.102 (4)	0.103 (4)	−0.026 (3)	0.017 (3)	0.001 (3)
C15	0.061 (3)	0.111 (4)	0.096 (4)	−0.008 (3)	0.015 (3)	−0.037 (3)
C16	0.086 (3)	0.122 (4)	0.072 (3)	0.000 (3)	0.010 (3)	0.000 (3)
C17	0.071 (3)	0.081 (3)	0.075 (3)	−0.014 (2)	0.008 (2)	0.002 (3)
C18	0.041 (2)	0.088 (3)	0.065 (3)	0.002 (2)	0.0099 (19)	−0.014 (2)
C19	0.070 (3)	0.079 (3)	0.086 (3)	−0.004 (2)	0.016 (2)	0.009 (3)
C20	0.077 (3)	0.081 (3)	0.113 (4)	−0.015 (3)	0.018 (3)	−0.010 (3)
C21	0.046 (2)	0.066 (3)	0.063 (2)	0.002 (2)	0.0094 (19)	0.002 (2)
C22	0.0417 (19)	0.062 (2)	0.054 (2)	−0.0021 (18)	0.0065 (16)	0.007 (2)
C23	0.0374 (19)	0.081 (3)	0.069 (2)	−0.0005 (19)	0.0063 (17)	−0.001 (2)
C24	0.043 (2)	0.082 (3)	0.069 (3)	−0.003 (2)	−0.0026 (17)	−0.003 (2)
C25	0.041 (2)	0.064 (3)	0.059 (2)	0.0010 (18)	0.0039 (17)	0.003 (2)
C26	0.042 (2)	0.082 (3)	0.070 (3)	0.007 (2)	0.0102 (18)	−0.007 (2)
C27	0.0359 (19)	0.087 (3)	0.081 (3)	0.0007 (19)	0.0022 (18)	−0.012 (2)
C28	0.066 (3)	0.087 (3)	0.103 (3)	0.012 (2)	0.015 (2)	−0.021 (3)

Geometric parameters (Å, º) top

O1—C7	1.355 (5)	C10—H10A	0.9300
O1—C4	1.381 (4)	C11—C12	1.385 (5)
O2—C7	1.195 (4)	C12—C13	1.367 (5)
O3—C11	1.372 (4)	C12—H12A	0.9300
O3—C14	1.411 (4)	C13—H13A	0.9300
O4—C21	1.366 (4)	C14—H14A	0.9600
O4—C18	1.403 (4)	C14—H14B	0.9600
O5—C21	1.203 (4)	C14—H14C	0.9600
O6—C25	1.371 (4)	C15—C20	1.349 (6)
O6—C28	1.414 (4)	C15—C16	1.358 (6)
N1—C7	1.332 (5)	C15—H15A	0.9300
N1—C8	1.418 (5)	C16—C17	1.371 (6)
N1—H1A	0.8600	C16—H16A	0.9300
N2—C21	1.335 (4)	C17—C18	1.362 (5)
N2—C22	1.414 (4)	C17—H17A	0.9300
N2—H2B	0.8600	C18—C19	1.359 (5)
C1—C6	1.279 (6)	C19—C20	1.369 (6)
C1—C2	1.445 (4)	C19—H19A	0.9300
C1—H1B	0.9300	C20—H20A	0.9300
C2—C3	1.371 (7)	C22—C27	1.376 (5)
C2—H2A	0.9300	C22—C23	1.378 (5)
C3—C4	1.344 (5)	C23—C24	1.368 (5)
C3—H3A	0.9300	C23—H23A	0.9300
C4—C5	1.383 (5)	C24—C25	1.382 (5)
C5—C6	1.337 (6)	C24—H24A	0.9300
C5—H5A	0.9300	C25—C26	1.357 (5)
C6—H6A	0.9300	C26—C27	1.380 (5)
C8—C9	1.374 (5)	C26—H26A	0.9300
C8—C13	1.382 (5)	C27—H27A	0.9300
C9—C10	1.374 (5)	C28—H28A	0.9600
C9—H9A	0.9300	C28—H28B	0.9600
C10—C11	1.372 (5)	C28—H28C	0.9600

C7—O1—C4	120.3 (3)	O3—C14—H14B	109.5
C11—O3—C14	118.0 (3)	H14A—C14—H14B	109.5
C21—O4—C18	116.4 (3)	O3—C14—H14C	109.5
C25—O6—C28	117.2 (3)	H14A—C14—H14C	109.5
C7—N1—C8	125.9 (3)	H14B—C14—H14C	109.5
C7—N1—H1A	117.0	C20—C15—C16	120.0 (5)
C8—N1—H1A	117.0	C20—C15—H15A	120.0
C21—N2—C22	126.9 (3)	C16—C15—H15A	120.0
C21—N2—H2B	116.6	C15—C16—C17	120.6 (5)
C22—N2—H2B	116.6	C15—C16—H16A	119.7
C6—C1—C2	119.2 (5)	C17—C16—H16A	119.7
C6—C1—H1B	120.4	C18—C17—C16	118.7 (4)
C2—C1—H1B	120.4	C18—C17—H17A	120.6
C3—C2—C1	117.2 (5)	C16—C17—H17A	120.6
C3—C2—H2A	121.4	C19—C18—C17	121.0 (4)
C1—C2—H2A	121.4	C19—C18—O4	120.1 (4)
C4—C3—C2	120.8 (5)	C17—C18—O4	118.8 (4)
C4—C3—H3A	119.6	C18—C19—C20	119.3 (4)
C2—C3—H3A	119.6	C18—C19—H19A	120.3
C3—C4—O1	120.5 (4)	C20—C19—H19A	120.3
C3—C4—C5	119.9 (4)	C15—C20—C19	120.4 (5)
O1—C4—C5	119.3 (4)	C15—C20—H20A	119.8
C6—C5—C4	118.9 (4)	C19—C20—H20A	119.8
C6—C5—H5A	120.5	O5—C21—N2	128.2 (4)
C4—C5—H5A	120.5	O5—C21—O4	122.9 (3)
C1—C6—C5	123.9 (5)	N2—C21—O4	108.9 (3)
C1—C6—H6A	118.1	C27—C22—C23	117.9 (4)
C5—C6—H6A	118.1	C27—C22—N2	124.4 (3)
O2—C7—N1	127.8 (4)	C23—C22—N2	117.7 (3)
O2—C7—O1	123.0 (4)	C24—C23—C22	120.8 (3)
N1—C7—O1	109.2 (3)	C24—C23—H23A	119.6
C9—C8—C13	118.8 (4)	C22—C23—H23A	119.6
C9—C8—N1	122.3 (4)	C23—C24—C25	121.1 (3)
C13—C8—N1	118.8 (3)	C23—C24—H24A	119.5
C8—C9—C10	120.6 (4)	C25—C24—H24A	119.5
C8—C9—H9A	119.7	C26—C25—O6	125.2 (3)
C10—C9—H9A	119.7	C26—C25—C24	118.3 (4)
C11—C10—C9	120.6 (4)	O6—C25—C24	116.4 (3)
C11—C10—H10A	119.7	C25—C26—C27	121.0 (3)
C9—C10—H10A	119.7	C25—C26—H26A	119.5
O3—C11—C10	125.3 (4)	C27—C26—H26A	119.5
O3—C11—C12	115.7 (4)	C22—C27—C26	120.9 (3)
C10—C11—C12	118.9 (4)	C22—C27—H27A	119.5
C13—C12—C11	120.4 (4)	C26—C27—H27A	119.5
C13—C12—H12A	119.8	O6—C28—H28A	109.5
C11—C12—H12A	119.8	O6—C28—H28B	109.5
C12—C13—C8	120.6 (4)	H28A—C28—H28B	109.5
C12—C13—H13A	119.7	O6—C28—H28C	109.5
C8—C13—H13A	119.7	H28A—C28—H28C	109.5
O3—C14—H14A	109.5	H28B—C28—H28C	109.5

C6—C1—C2—C3	2.7 (8)	C20—C15—C16—C17	0.2 (7)
C1—C2—C3—C4	−0.7 (7)	C15—C16—C17—C18	0.0 (6)
C2—C3—C4—O1	173.6 (4)	C16—C17—C18—C19	−0.3 (6)
C2—C3—C4—C5	−0.9 (7)	C16—C17—C18—O4	176.2 (3)
C7—O1—C4—C3	106.2 (5)	C21—O4—C18—C19	−91.7 (4)
C7—O1—C4—C5	−79.3 (5)	C21—O4—C18—C17	91.7 (4)
C3—C4—C5—C6	0.5 (6)	C17—C18—C19—C20	0.4 (6)
O1—C4—C5—C6	−174.0 (3)	O4—C18—C19—C20	−176.0 (3)
C2—C1—C6—C5	−3.3 (7)	C16—C15—C20—C19	−0.1 (7)
C4—C5—C6—C1	1.7 (7)	C18—C19—C20—C15	−0.2 (6)
C8—N1—C7—O2	0.3 (8)	C22—N2—C21—O5	−4.3 (6)
C8—N1—C7—O1	179.2 (3)	C22—N2—C21—O4	175.8 (3)
C4—O1—C7—O2	−0.4 (7)	C18—O4—C21—O5	4.5 (6)
C4—O1—C7—N1	−179.4 (4)	C18—O4—C21—N2	−175.5 (3)
C7—N1—C8—C9	−34.6 (6)	C21—N2—C22—C27	−5.7 (6)
C7—N1—C8—C13	145.2 (4)	C21—N2—C22—C23	174.9 (3)
C13—C8—C9—C10	−0.8 (6)	C27—C22—C23—C24	−0.8 (5)
N1—C8—C9—C10	179.0 (3)	N2—C22—C23—C24	178.6 (3)
C8—C9—C10—C11	0.5 (6)	C22—C23—C24—C25	−0.7 (6)
C14—O3—C11—C10	−5.6 (5)	C28—O6—C25—C26	−18.3 (5)
C14—O3—C11—C12	171.3 (3)	C28—O6—C25—C24	165.1 (3)
C9—C10—C11—O3	177.2 (3)	C23—C24—C25—C26	1.7 (6)
C9—C10—C11—C12	0.3 (6)	C23—C24—C25—O6	178.6 (3)
O3—C11—C12—C13	−177.8 (3)	O6—C25—C26—C27	−177.9 (3)
C10—C11—C12—C13	−0.7 (6)	C24—C25—C26—C27	−1.3 (6)
C11—C12—C13—C8	0.3 (6)	C23—C22—C27—C26	1.2 (5)
C9—C8—C13—C12	0.4 (6)	N2—C22—C27—C26	−178.1 (3)
N1—C8—C13—C12	−179.3 (3)	C25—C26—C27—C22	−0.2 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5	0.86	2.19	3.038 (4)	170
N2—H2B···O2ⁱ	0.86	2.22	3.062 (4)	166
C6—H6A···O5ⁱⁱ	0.93	2.58	3.435 (5)	153
C9—H9A···O2	0.93	2.52	2.967 (5)	110
C23—H23A···O2ⁱ	0.93	2.60	3.390 (4)	144
C27—H27A···O5	0.93	2.30	2.907 (5)	122

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₃
M_r	243.25
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	9.869 (2), 10.870 (2), 23.319 (5)
β (°)	100.27 (3)
V (Å³)	2461.5 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
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	0.973, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	4733, 4459, 2109
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.184, 1.03
No. of reflections	4459
No. of parameters	319
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.34

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5	0.86	2.19	3.038 (4)	170
N2—H2B···O2ⁱ	0.86	2.22	3.062 (4)	166
C6—H6A···O5ⁱⁱ	0.93	2.58	3.435 (5)	153
C9—H9A···O2	0.93	2.52	2.967 (5)	110
C23—H23A···O2ⁱ	0.93	2.60	3.390 (4)	144
C27—H27A···O5	0.93	2.30	2.907 (5)	122

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

Acknowledgements

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