Benzyl N-(4-pyrid­yl)carbamate

Fang, H.; Fang, M.-J.; Zhang, Y.-P.

doi:10.1107/S160053681000098X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o401

https://doi.org/10.1107/S160053681000098X

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Benzyl N-(4-pyridyl)carbamate

Hua Fang,^a Mei-Juan Fang ^b ^* and Yi-Ping Zhang ^a

^aThe Third Institute of Oceanography of the State Oceanic Administration, Xiamen 361005, People's Republic of China, and ^bDepartment of Pharmaceutical Science, Medical College, Xiamen University, Xiamen 361005, People's Republic of China
^*Correspondence e-mail: fangmj@xmu.edu.cn

(Received 6 January 2010; accepted 8 January 2010; online 20 January 2010)

The title compound, C₁₃H₁₂N₂O₂, was obtained by the reaction of 4-aminopyridine and benzyl chloroformate in tetrahydrofuran. The crystal structure contains N—H⋯N hydrogen bonds between two unique molecules within layers and antiparallel C—O⋯O—C interactions [O⋯O = 3.06 (3) Å] between the two molecules of the asymmetric unit.

Related literature

The title compound was synthesized in order to investigate the nature of its reversion tetrodotoxin-induced cardiorespiratory depression, see: Chang et al. (1997 ). For a related structure, see: Zheng et al. (2005 ).

Experimental

Crystal data

C₁₃H₁₂N₂O₂
M_r = 228.25
Monoclinic, P 2₁ /c
a = 11.9439 (5) Å
b = 13.2120 (6) Å
c = 14.6574 (7) Å
β = 98.418 (4)°
V = 2288.06 (18) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.22 × 0.18 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.973, T_max = 0.984
11332 measured reflections
4028 independent reflections
2831 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.070
S = 1.05
4028 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2′—H2′C⋯N1ⁱ	0.86	2.09	2.9460 (16)	171
N2—H2C⋯N1′ⁱⁱ	0.86	2.11	2.9630 (18)	170
Symmetry codes: (i) -x+1, -y, -z; (ii) -x, -y, -z.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681000098X/jh2125sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681000098X/jh2125Isup2.hkl

checkCIF report

Comment top

The title compound, (I), a 4-aminopyridine analog, was synthesized for investigation of the nature of its reversion tetrodotoxin-induced cardiorespiratorydepression (Chang et al., 1997). The crystal packing is stabilized by stronger N-H···N hydrogen bonds between molecules within layers and antiparallel C-O ··· O-C interactions between the two molecules of the asymmetric unit, and bond lengths and angles are in agreement with values reported for a similar compound (Zheng et al., 2005). The dihedral angle between the planes of the phenzene ring and pyridine ring systems is 66.2 (3) °.

Related literature top

For related literature, see: Zheng et al. (2005); Chang et al. (1997).

Experimental top

A solution of dry tetrahydrofuran (15 ml) containing 4-aminopyridine (5 mmol, 0.47 g) and triethylamine (0.70 ml) was added dropwise to the solution of tetrahydrofuran (15 ml) containing the benzyl chloroformate (5 mmol, 0.85 g). The reaction mixture was stirred for 6 h in ice bath and the solvent was then removed under reduced pressure to give a residue, which was extracted with ethyl acetate (3 × 15 ml). The solution was dried over anhydrous MgSO₄ and concentrated under vacuum to obtain a slurry residue, which was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 2:1) to give products I as colorless amorphous solids. Single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of a petroleum ether /dichloromethane solution (1:1 v/v).

Structure description top

For related literature, see: Zheng et al. (2005); Chang et al. (1997).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEPII (Farrugia, 1997) plot of the title molecule with displacement ellipsoids srawn at the 30% probability level. H atoms are drawn as spheres of arbitrary radii.
	Fig. 2. The formation of the title compound.

Benzyl N-(4-pyridyl)carbamate top

Crystal data top

C₁₃H₁₂N₂O₂	F(000) = 960
M_r = 228.25	D_x = 1.325 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2895 reflections
a = 11.9439 (5) Å	θ = 2.1–26.4°
b = 13.2120 (6) Å	µ = 0.09 mm⁻¹
c = 14.6574 (7) Å	T = 293 K
β = 98.418 (4)°	Chunk, colorless
V = 2288.06 (18) Å³	0.30 × 0.22 × 0.18 mm
Z = 8

Data collection top

Bruker APEX area-detector diffractometer	4028 independent reflections
Radiation source: fine-focus sealed tube	2831 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
φ and ω scan	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −14→12
T_min = 0.973, T_max = 0.984	k = −15→15
11332 measured reflections	l = −17→17

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.070	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0229P)² + 0.110P] where P = (F_o² + 2F_c²)/3
4028 reflections	(Δ/σ)_max < 0.001
307 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₃H₁₂N₂O₂	V = 2288.06 (18) Å³
M_r = 228.25	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.9439 (5) Å	µ = 0.09 mm⁻¹
b = 13.2120 (6) Å	T = 293 K
c = 14.6574 (7) Å	0.30 × 0.22 × 0.18 mm
β = 98.418 (4)°

Data collection top

Bruker APEX area-detector diffractometer	4028 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2831 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.984	R_int = 0.039
11332 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.070	H-atom parameters constrained
S = 1.05	Δρ_max = 0.17 e Å⁻³
4028 reflections	Δρ_min = −0.17 e Å⁻³
307 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
N2'	0.16150 (9)	0.18181 (9)	−0.00328 (9)	0.0227 (3)
H2'C	0.2140	0.1458	−0.0216	0.027*
O1	0.42587 (8)	0.17805 (9)	0.26686 (8)	0.0335 (3)
O2	0.24197 (8)	0.13329 (8)	0.22775 (8)	0.0330 (3)
O1'	0.13791 (8)	0.32072 (8)	0.08678 (8)	0.0301 (3)
O2'	0.30953 (8)	0.27290 (8)	0.05366 (8)	0.0288 (3)
N2	0.36888 (9)	0.04846 (9)	0.16579 (9)	0.0240 (3)
H2C	0.3088	0.0179	0.1403	0.029*
C1	0.35408 (12)	0.12531 (12)	0.22453 (11)	0.0241 (4)
N1'	−0.16725 (10)	0.07480 (10)	−0.09588 (10)	0.0297 (3)
C9	0.47128 (11)	0.01402 (12)	0.14254 (10)	0.0217 (4)
C3'	0.48132 (13)	0.36576 (11)	0.08454 (12)	0.0269 (4)
C13	0.57368 (12)	0.06602 (13)	0.16021 (12)	0.0292 (4)
H13A	0.5789	0.1278	0.1909	0.035*
C10	0.47072 (12)	−0.07770 (12)	0.09719 (11)	0.0254 (4)
H10A	0.4040	−0.1147	0.0844	0.031*
C1'	0.19585 (12)	0.26347 (12)	0.04966 (11)	0.0229 (4)
C9'	0.05051 (12)	0.14969 (11)	−0.03138 (11)	0.0200 (4)
C10'	0.03345 (12)	0.07278 (12)	−0.09590 (11)	0.0244 (4)
H10B	0.0948	0.0447	−0.1193	0.029*
C13'	−0.04470 (12)	0.18983 (12)	0.00023 (11)	0.0257 (4)
H13B	−0.0382	0.2421	0.0432	0.031*
N1	0.66870 (10)	−0.06576 (10)	0.08657 (9)	0.0290 (3)
C11'	−0.07391 (12)	0.03782 (12)	−0.12545 (12)	0.0281 (4)
H11A	−0.0827	−0.0144	−0.1684	0.034*
C3	0.09174 (12)	0.16792 (12)	0.31022 (11)	0.0243 (4)
C11	0.56904 (12)	−0.11411 (12)	0.07098 (12)	0.0283 (4)
H11B	0.5662	−0.1760	0.0406	0.034*
C2'	0.36095 (12)	0.36077 (12)	0.10249 (12)	0.0333 (4)
H2'A	0.3585	0.3543	0.1681	0.040*
H2'B	0.3206	0.4218	0.0804	0.040*
C12	0.66733 (12)	0.02252 (13)	0.13053 (12)	0.0328 (4)
H12A	0.7352	0.0579	0.1422	0.039*
C8	−0.00463 (13)	0.21433 (13)	0.26577 (12)	0.0320 (4)
H8A	0.0015	0.2712	0.2294	0.038*
C4	0.08082 (15)	0.08481 (13)	0.36471 (12)	0.0367 (4)
H4A	0.1454	0.0542	0.3961	0.044*
C2	0.20694 (13)	0.20348 (13)	0.29487 (12)	0.0348 (5)
H2A	0.2034	0.2721	0.2711	0.042*
H2B	0.2594	0.2017	0.3520	0.042*
C4'	0.50592 (14)	0.36917 (12)	−0.00500 (13)	0.0351 (4)
H4'A	0.4472	0.3691	−0.0543	0.042*
C8'	0.56941 (14)	0.36833 (13)	0.15684 (13)	0.0388 (5)
H8'A	0.5545	0.3653	0.2173	0.047*
C12'	−0.14897 (12)	0.14942 (12)	−0.03432 (12)	0.0309 (4)
H12B	−0.2119	0.1767	−0.0127	0.037*
C5'	0.61669 (16)	0.37268 (13)	−0.02173 (15)	0.0465 (5)
H5'A	0.6322	0.3726	−0.0821	0.056*
C6	−0.12000 (16)	0.09262 (18)	0.32858 (15)	0.0521 (6)
H6A	−0.1911	0.0671	0.3345	0.063*
C7	−0.11059 (14)	0.17636 (16)	0.27524 (14)	0.0453 (5)
H7A	−0.1754	0.2079	0.2453	0.054*
C7'	0.68094 (15)	0.37554 (14)	0.13934 (17)	0.0522 (6)
H7'A	0.7400	0.3799	0.1882	0.063*
C6'	0.70368 (16)	0.37628 (14)	0.05031 (18)	0.0524 (6)
H6'A	0.7782	0.3792	0.0388	0.063*
C5	−0.02418 (18)	0.04609 (15)	0.37357 (14)	0.0495 (6)
H5A	−0.0304	−0.0110	0.4096	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2'	0.0176 (7)	0.0229 (7)	0.0278 (8)	0.0018 (5)	0.0046 (6)	−0.0046 (7)
O1	0.0266 (6)	0.0403 (7)	0.0339 (7)	−0.0061 (5)	0.0051 (6)	−0.0154 (6)
O2	0.0215 (6)	0.0421 (7)	0.0365 (7)	0.0007 (5)	0.0081 (5)	−0.0205 (6)
O1'	0.0277 (6)	0.0280 (7)	0.0356 (7)	0.0020 (5)	0.0078 (5)	−0.0092 (6)
O2'	0.0214 (6)	0.0273 (7)	0.0383 (7)	−0.0062 (4)	0.0065 (5)	−0.0115 (6)
N2	0.0162 (7)	0.0282 (8)	0.0276 (8)	−0.0019 (5)	0.0028 (6)	−0.0090 (7)
C1	0.0233 (9)	0.0283 (10)	0.0212 (9)	0.0012 (7)	0.0051 (7)	−0.0013 (8)
N1'	0.0224 (7)	0.0310 (9)	0.0357 (9)	−0.0012 (6)	0.0043 (6)	−0.0044 (7)
C9	0.0185 (8)	0.0276 (10)	0.0191 (9)	0.0019 (6)	0.0030 (7)	0.0019 (8)
C3'	0.0293 (9)	0.0198 (9)	0.0318 (11)	−0.0058 (7)	0.0054 (8)	−0.0060 (8)
C13	0.0241 (9)	0.0307 (10)	0.0330 (11)	−0.0027 (7)	0.0048 (8)	−0.0103 (9)
C10	0.0205 (8)	0.0269 (10)	0.0295 (10)	−0.0034 (7)	0.0055 (7)	−0.0029 (8)
C1'	0.0242 (9)	0.0223 (9)	0.0221 (9)	−0.0004 (7)	0.0033 (7)	0.0016 (8)
C9'	0.0192 (8)	0.0202 (9)	0.0206 (9)	−0.0012 (6)	0.0028 (7)	0.0039 (7)
C10'	0.0203 (8)	0.0265 (9)	0.0271 (10)	0.0009 (7)	0.0061 (7)	−0.0019 (8)
C13'	0.0239 (9)	0.0262 (10)	0.0271 (10)	0.0012 (7)	0.0044 (7)	−0.0036 (8)
N1	0.0222 (7)	0.0331 (9)	0.0317 (9)	0.0007 (6)	0.0047 (6)	−0.0040 (7)
C11'	0.0271 (9)	0.0271 (10)	0.0305 (10)	−0.0019 (7)	0.0055 (8)	−0.0047 (8)
C3	0.0266 (9)	0.0256 (9)	0.0213 (10)	0.0015 (7)	0.0056 (7)	−0.0087 (8)
C11	0.0258 (9)	0.0263 (10)	0.0331 (11)	0.0001 (7)	0.0055 (8)	−0.0047 (8)
C2'	0.0333 (10)	0.0257 (10)	0.0416 (12)	−0.0096 (7)	0.0083 (9)	−0.0127 (9)
C12	0.0205 (9)	0.0409 (12)	0.0370 (11)	−0.0067 (7)	0.0044 (8)	−0.0096 (9)
C8	0.0373 (10)	0.0330 (11)	0.0258 (10)	0.0034 (8)	0.0051 (8)	−0.0031 (8)
C4	0.0448 (11)	0.0343 (11)	0.0298 (11)	0.0040 (8)	0.0019 (9)	−0.0028 (9)
C2	0.0327 (10)	0.0393 (11)	0.0347 (11)	−0.0014 (8)	0.0120 (8)	−0.0194 (9)
C4'	0.0386 (10)	0.0310 (10)	0.0357 (11)	−0.0110 (8)	0.0058 (9)	−0.0024 (9)
C8'	0.0431 (11)	0.0353 (11)	0.0357 (12)	−0.0068 (8)	−0.0021 (9)	−0.0078 (9)
C12'	0.0213 (9)	0.0340 (11)	0.0387 (11)	0.0033 (7)	0.0088 (8)	−0.0030 (9)
C5'	0.0514 (13)	0.0368 (12)	0.0574 (14)	−0.0174 (9)	0.0287 (11)	−0.0123 (10)
C6	0.0404 (12)	0.0747 (16)	0.0449 (14)	−0.0236 (11)	0.0189 (11)	−0.0234 (12)
C7	0.0291 (10)	0.0607 (14)	0.0442 (13)	0.0035 (9)	−0.0009 (9)	−0.0149 (12)
C7'	0.0303 (11)	0.0444 (13)	0.0755 (17)	−0.0052 (8)	−0.0141 (11)	−0.0119 (12)
C6'	0.0327 (11)	0.0376 (12)	0.090 (2)	−0.0091 (9)	0.0212 (13)	−0.0203 (12)
C5	0.0732 (15)	0.0442 (13)	0.0340 (12)	−0.0213 (11)	0.0174 (11)	−0.0027 (10)

Geometric parameters (Å, º) top

N2'—C1'	1.3569 (19)	N1—C11	1.3407 (19)
N2'—C9'	1.3954 (17)	C11'—H11A	0.9300
N2'—H2'C	0.8600	C3—C4	1.375 (2)
O1—C1	1.2042 (18)	C3—C8	1.380 (2)
O2—C1	1.3509 (16)	C3—C2	1.502 (2)
O2—C2	1.4572 (17)	C11—H11B	0.9300
O1'—C1'	1.2072 (17)	C2'—H2'A	0.9700
O2'—C1'	1.3561 (16)	C2'—H2'B	0.9700
O2'—C2'	1.4520 (17)	C12—H12A	0.9300
N2—C1	1.3595 (19)	C8—C7	1.387 (2)
N2—C9	1.3932 (17)	C8—H8A	0.9300
N2—H2C	0.8600	C4—C5	1.378 (2)
N1'—C12'	1.333 (2)	C4—H4A	0.9300
N1'—C11'	1.3457 (18)	C2—H2A	0.9700
C9—C10	1.382 (2)	C2—H2B	0.9700
C9—C13	1.394 (2)	C4'—C5'	1.381 (2)
C3'—C4'	1.387 (2)	C4'—H4'A	0.9300
C3'—C8'	1.380 (2)	C8'—C7'	1.396 (2)
C3'—C2'	1.500 (2)	C8'—H8'A	0.9300
C13—C12	1.383 (2)	C12'—H12B	0.9300
C13—H13A	0.9300	C5'—C6'	1.369 (3)
C10—C11	1.3749 (19)	C5'—H5'A	0.9300
C10—H10A	0.9300	C6—C7	1.369 (3)
C9'—C10'	1.383 (2)	C6—C5	1.379 (3)
C9'—C13'	1.3940 (19)	C6—H6A	0.9300
C10'—C11'	1.372 (2)	C7—H7A	0.9300
C10'—H10B	0.9300	C7'—C6'	1.371 (3)
C13'—C12'	1.381 (2)	C7'—H7'A	0.9300
C13'—H13B	0.9300	C6'—H6'A	0.9300
N1—C12	1.334 (2)	C5—H5A	0.9300

C1'—N2'—C9'	127.25 (12)	O2'—C2'—H2'A	110.3
C1'—N2'—H2'C	116.4	C3'—C2'—H2'A	110.3
C9'—N2'—H2'C	116.4	O2'—C2'—H2'B	110.3
C1—O2—C2	117.22 (12)	C3'—C2'—H2'B	110.3
C1'—O2'—C2'	116.32 (11)	H2'A—C2'—H2'B	108.5
C1—N2—C9	126.80 (13)	N1—C12—C13	125.66 (14)
C1—N2—H2C	116.6	N1—C12—H12A	117.2
C9—N2—H2C	116.6	C13—C12—H12A	117.2
O1—C1—O2	124.86 (14)	C7—C8—C3	120.14 (17)
O1—C1—N2	127.57 (13)	C7—C8—H8A	119.9
O2—C1—N2	107.58 (13)	C3—C8—H8A	119.9
C12'—N1'—C11'	115.17 (13)	C3—C4—C5	121.07 (18)
C10—C9—N2	117.48 (13)	C3—C4—H4A	119.5
C10—C9—C13	117.66 (13)	C5—C4—H4A	119.5
N2—C9—C13	124.85 (14)	O2—C2—C3	105.19 (12)
C4'—C3'—C8'	118.84 (15)	O2—C2—H2A	110.7
C4'—C3'—C2'	120.56 (16)	C3—C2—H2A	110.7
C8'—C3'—C2'	120.59 (15)	O2—C2—H2B	110.7
C12—C13—C9	117.70 (15)	C3—C2—H2B	110.7
C12—C13—H13A	121.2	H2A—C2—H2B	108.8
C9—C13—H13A	121.2	C3'—C4'—C5'	120.68 (18)
C9—C10—C11	119.81 (14)	C3'—C4'—H4'A	119.7
C9—C10—H10A	120.1	C5'—C4'—H4'A	119.7
C11—C10—H10A	120.1	C3'—C8'—C7'	120.08 (18)
O1'—C1'—O2'	124.01 (14)	C3'—C8'—H8'A	120.0
O1'—C1'—N2'	127.63 (14)	C7'—C8'—H8'A	120.0
O2'—C1'—N2'	108.35 (12)	N1'—C12'—C13'	125.71 (14)
C10'—C9'—N2'	117.64 (12)	N1'—C12'—H12B	117.1
C10'—C9'—C13'	117.46 (14)	C13'—C12'—H12B	117.1
N2'—C9'—C13'	124.90 (14)	C6'—C5'—C4'	120.17 (19)
C9'—C10'—C11'	120.04 (13)	C6'—C5'—H5'A	119.9
C9'—C10'—H10B	120.0	C4'—C5'—H5'A	119.9
C11'—C10'—H10B	120.0	C7—C6—C5	120.11 (17)
C12'—C13'—C9'	117.82 (15)	C7—C6—H6A	119.9
C12'—C13'—H13B	121.1	C5—C6—H6A	119.9
C9'—C13'—H13B	121.1	C6—C7—C8	120.13 (18)
C12—N1—C11	115.19 (12)	C6—C7—H7A	119.9
N1'—C11'—C10'	123.78 (16)	C8—C7—H7A	119.9
N1'—C11'—H11A	118.1	C6'—C7'—C8'	120.2 (2)
C10'—C11'—H11A	118.1	C6'—C7'—H7'A	119.9
C4—C3—C8	119.03 (15)	C8'—C7'—H7'A	119.9
C4—C3—C2	120.24 (15)	C5'—C6'—C7'	119.99 (17)
C8—C3—C2	120.62 (16)	C5'—C6'—H6'A	120.0
N1—C11—C10	123.99 (15)	C7'—C6'—H6'A	120.0
N1—C11—H11B	118.0	C6—C5—C4	119.50 (19)
C10—C11—H11B	118.0	C6—C5—H5A	120.2
O2'—C2'—C3'	107.20 (12)	C4—C5—H5A	120.2

C2—O2—C1—O1	−7.0 (2)	C4'—C3'—C2'—O2'	56.18 (19)
C2—O2—C1—N2	173.09 (13)	C8'—C3'—C2'—O2'	−124.65 (17)
C9—N2—C1—O1	0.4 (3)	C11—N1—C12—C13	0.1 (3)
C9—N2—C1—O2	−179.66 (14)	C9—C13—C12—N1	−0.4 (3)
C1—N2—C9—C10	166.73 (15)	C4—C3—C8—C7	−0.9 (2)
C1—N2—C9—C13	−14.4 (2)	C2—C3—C8—C7	175.37 (15)
C10—C9—C13—C12	0.5 (2)	C8—C3—C4—C5	1.6 (2)
N2—C9—C13—C12	−178.37 (15)	C2—C3—C4—C5	−174.66 (15)
N2—C9—C10—C11	178.65 (15)	C1—O2—C2—C3	−157.99 (14)
C13—C9—C10—C11	−0.3 (2)	C4—C3—C2—O2	77.04 (18)
C2'—O2'—C1'—O1'	−3.0 (2)	C8—C3—C2—O2	−99.19 (16)
C2'—O2'—C1'—N2'	175.94 (13)	C8'—C3'—C4'—C5'	1.5 (2)
C9'—N2'—C1'—O1'	4.4 (3)	C2'—C3'—C4'—C5'	−179.31 (14)
C9'—N2'—C1'—O2'	−174.45 (13)	C4'—C3'—C8'—C7'	0.8 (3)
C1'—N2'—C9'—C10'	171.04 (15)	C2'—C3'—C8'—C7'	−178.39 (15)
C1'—N2'—C9'—C13'	−8.5 (2)	C11'—N1'—C12'—C13'	−0.2 (2)
N2'—C9'—C10'—C11'	179.55 (14)	C9'—C13'—C12'—N1'	−0.1 (2)
C13'—C9'—C10'—C11'	−0.9 (2)	C3'—C4'—C5'—C6'	−2.2 (3)
C10'—C9'—C13'—C12'	0.6 (2)	C5—C6—C7—C8	0.4 (3)
N2'—C9'—C13'—C12'	−179.87 (14)	C3—C8—C7—C6	−0.1 (3)
C12'—N1'—C11'—C10'	−0.1 (2)	C3'—C8'—C7'—C6'	−2.4 (3)
C9'—C10'—C11'—N1'	0.7 (2)	C4'—C5'—C6'—C7'	0.5 (3)
C12—N1—C11—C10	0.1 (2)	C8'—C7'—C6'—C5'	1.8 (3)
C9—C10—C11—N1	0.0 (3)	C7—C6—C5—C4	0.3 (3)
C1'—O2'—C2'—C3'	−170.42 (13)	C3—C4—C5—C6	−1.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2′—H2′C···N1ⁱ	0.86	2.09	2.9460 (16)	171
N2—H2C···N1′ⁱⁱ	0.86	2.11	2.9630 (18)	170

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂N₂O₂
M_r	228.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.9439 (5), 13.2120 (6), 14.6574 (7)
β (°)	98.418 (4)
V (Å³)	2288.06 (18)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.22 × 0.18

Data collection
Diffractometer	Bruker APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.973, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	11332, 4028, 2831
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.070, 1.05
No. of reflections	4028
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.17

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2'—H2'C···N1ⁱ	0.86	2.09	2.9460 (16)	171.1
N2—H2C···N1'ⁱⁱ	0.86	2.11	2.9630 (18)	170.4

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

Acknowledgements

This work was supported by the Science and Technology Program of the Oceans and Fisheries Bureau of Xiamen (grant No. 200911) and the Natural Science Foundation of Fujian Province of China (grant No. 2009 J05099).

References

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Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
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