1-Benzyl-N-methyl-1H-pyrrole-2-carboxamide

Zeng, X.C.; Li, K.P.; Hu, F.; Zheng, L.

doi:10.1107/S160053681002787X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o2051

https://doi.org/10.1107/S160053681002787X

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1-Benzyl-N-methyl-1H-pyrrole-2-carboxamide

Xiang Chao Zeng,^a ^* Kai Ping Li,^a Fang Hu ^a and Le Zheng ^a

^aDepartment of Chemistry, Jinan University, Guangzhou, Guangdong 510632, People's Republic of China
^*Correspondence e-mail: xczeng@126.com

(Received 2 July 2010; accepted 13 July 2010; online 17 July 2010)

The asymmetric unit of the title compound, C₁₃H₁₄N₂O, contains two independent molecules, which differ in the twist of the phenyl ring: the N_pyrrole—C(H₂)—C—C torsion angles are −73.0 (3) and 17.1 (3)°. In the crystal structure, molecules are linked through N—H⋯O hydrogen bonds into chains extending along the a axis.

Related literature

For the bioactivity of pyrrole derivatives, see: Fabio et al. (2007 ); Banwell et al. (2006 ). For related structures, see: Zeng et al. (2007 ); Li et al. (2009 ).

Experimental

Crystal data

C₁₃H₁₄N₂O
M_r = 214.26
Monoclinic, P 2₁ /c
a = 9.8285 (18) Å
b = 23.588 (4) Å
c = 9.9230 (17) Å
β = 90.107 (3)°
V = 2300.5 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 110 K
0.45 × 0.43 × 0.41 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.965, T_max = 0.968
10728 measured reflections
4879 independent reflections
4388 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.157
S = 1.03
4879 reflections
300 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O1ⁱ	0.87 (3)	2.04 (3)	2.869 (2)	161 (3)
N2—H2A⋯O3ⁱⁱ	0.86 (4)	2.10 (4)	2.902 (2)	154 (3)
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z-1.

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681002787X/cv2741sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681002787X/cv2741Isup2.hkl

checkCIF report

Comment top

Many pyrrole derivatives show important bioactivities, such as metabotropic receptor antagonists (Fabio et al., 2007) and antitumor activity (Banwell et al., 2006). This is the reason they have attracted our interest. This study is related to our previous structural investigations of methyl 2-(4,5-dibromo-1H-pyrrole-2-carboxamido)propionate (Zeng et al., 2007) and 3-(1-ethyl-1H-pyrrole-2-carboxamido) propionic acid monohydrate (Li et al., 2009).

In the molecule of the title compound(Fig.1), bond lengths and angles are unexceptional. In the crystal structure, molecules are linked through N—H···O hydrogen bonds, forming chains extending to the a axis (Fig. 2).

Related literature top

For the bioactivity of pyrrole derivatives, see: Fabio et al. (2007); Banwell et al. (2006). For related structures, see: Zeng et al. (2007); Li et al. (2009).

Experimental top

A suspension of potassium carbonate (4.21 g, 30 mmol), chloromethylbenzene (1.7 ml, 15 mmol), Pyrrole-2-carboxylic acid methylamide (1.24 g, 10 mmol) and Tetrabutylammoniumbromide (0.1 g) in acetonitrile (25 ml) magnetically stirred at 353 K for 18 h. After filtration, the filtrate was evaporated in vacuo, and the crude compound (I) was obtained. The impure product was dissolved in EtOH, colourless crystals suitable for X-ray analysis, m.p. 365 K, 92.1%, were obtained over a period of one week by slow evaporation at room temperature of the solution.

Structure description top

For the bioactivity of pyrrole derivatives, see: Fabio et al. (2007); Banwell et al. (2006). For related structures, see: Zeng et al. (2007); Li et al. (2009).

Computing details top

Data collection: SMART (Bruker,1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Two independent molecules of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Crystal packing of (I) showing the chains formed by hydrogen bonds (dashed lines).

1-Benzyl-N-methyl-1H-pyrrole-2-carboxamide top

Crystal data top

C₁₃H₁₄N₂O	D_x = 1.237 Mg m⁻³
M_r = 214.26	Melting point: 365 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.8285 (18) Å	Cell parameters from 7113 reflections
b = 23.588 (4) Å	θ = 2.2–27.0°
c = 9.9230 (17) Å	µ = 0.08 mm⁻¹
β = 90.107 (3)°	T = 110 K
V = 2300.5 (7) Å³	Prism, colourless
Z = 8	0.45 × 0.43 × 0.41 mm
F(000) = 912

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	4879 independent reflections
Radiation source: fine-focus sealed tube	4388 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
φ and ω scans	θ_max = 27.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.965, T_max = 0.968	k = −30→18
10728 measured reflections	l = −8→12

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.1044P)² + 0.2726P] where P = (F_o² + 2F_c²)/3
4879 reflections	(Δ/σ)_max = 0.001
300 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₃H₁₄N₂O	V = 2300.5 (7) Å³
M_r = 214.26	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.8285 (18) Å	µ = 0.08 mm⁻¹
b = 23.588 (4) Å	T = 110 K
c = 9.9230 (17) Å	0.45 × 0.43 × 0.41 mm
β = 90.107 (3)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	4879 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4388 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.968	R_int = 0.033
10728 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.24 e Å⁻³
4879 reflections	Δρ_min = −0.32 e Å⁻³
300 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
O3	0.26038 (14)	0.34460 (7)	1.12858 (15)	0.0345 (4)
N4	0.46989 (19)	0.36072 (8)	1.21438 (18)	0.0298 (4)
O1	0.75946 (15)	0.35421 (7)	0.24801 (16)	0.0351 (4)
C18	0.38669 (19)	0.34269 (8)	1.11684 (19)	0.0248 (4)
N3	0.38660 (18)	0.31280 (7)	0.87447 (16)	0.0278 (4)
C5	0.8847 (2)	0.34954 (8)	0.2623 (2)	0.0261 (4)
C4	0.94580 (19)	0.32331 (7)	0.3830 (2)	0.0251 (4)
N1	0.87834 (18)	0.31770 (7)	0.50486 (17)	0.0284 (4)
C3	1.0677 (2)	0.29404 (8)	0.3945 (2)	0.0299 (4)
H3	1.1347	0.2903	0.3262	0.036*
C21	0.2777 (2)	0.39956 (8)	0.7816 (2)	0.0276 (4)
C17	0.4525 (2)	0.31943 (8)	0.9961 (2)	0.0254 (4)
N2	0.97245 (19)	0.36613 (8)	0.16790 (19)	0.0325 (4)
C7	0.7549 (2)	0.34689 (9)	0.5492 (2)	0.0318 (4)
H7A	0.7010	0.3207	0.6058	0.038*
H7B	0.6994	0.3564	0.4690	0.038*
C16	0.5796 (2)	0.29413 (8)	0.9852 (2)	0.0305 (4)
H16	0.6469	0.2920	1.0539	0.037*
C25	0.3206 (3)	0.49865 (10)	0.8254 (3)	0.0427 (5)
H25	0.3390	0.5284	0.8873	0.051*
C15	0.5903 (3)	0.27231 (9)	0.8536 (2)	0.0378 (5)
H15	0.6659	0.2525	0.8170	0.045*
C8	0.7817 (2)	0.40061 (8)	0.6283 (2)	0.0289 (4)
C20	0.2580 (2)	0.33927 (9)	0.8305 (2)	0.0305 (4)
H20A	0.1931	0.3393	0.9067	0.037*
H20B	0.2178	0.3163	0.7569	0.037*
C19	0.4191 (2)	0.37479 (11)	1.3473 (2)	0.0387 (5)
H19A	0.3238	0.3867	1.3404	0.058*
H19B	0.4735	0.4057	1.3855	0.058*
H19C	0.4256	0.3414	1.4058	0.058*
C11	0.8202 (3)	0.50016 (11)	0.7752 (3)	0.0442 (5)
H11	0.8334	0.5341	0.8251	0.053*
C1	0.9583 (3)	0.28673 (8)	0.5899 (2)	0.0355 (5)
H1	0.9366	0.2775	0.6805	0.043*
C14	0.4714 (3)	0.28490 (8)	0.7884 (2)	0.0345 (5)
H14	0.4511	0.2757	0.6974	0.041*
C22	0.2682 (2)	0.41183 (9)	0.6454 (2)	0.0338 (5)
H22	0.2501	0.3822	0.5830	0.041*
C26	0.3042 (2)	0.44347 (9)	0.8715 (2)	0.0371 (5)
H26	0.3111	0.4357	0.9652	0.044*
C6	0.9276 (3)	0.38588 (13)	0.0361 (3)	0.0497 (6)
H6A	0.8989	0.3534	−0.0186	0.075*
H6B	1.0027	0.4055	−0.0090	0.075*
H6C	0.8510	0.4120	0.0470	0.075*
C9	0.6769 (2)	0.42377 (10)	0.7042 (2)	0.0379 (5)
H9	0.5909	0.4054	0.7066	0.045*
C2	1.0749 (2)	0.27108 (8)	0.5242 (2)	0.0347 (5)
H2	1.1469	0.2488	0.5601	0.042*
C13	0.9061 (2)	0.42821 (10)	0.6273 (2)	0.0378 (5)
H13	0.9790	0.4132	0.5756	0.045*
C23	0.2847 (3)	0.46671 (10)	0.5993 (2)	0.0423 (5)
H23	0.2785	0.4746	0.5056	0.051*
C10	0.6962 (3)	0.47337 (11)	0.7765 (3)	0.0447 (6)
H10	0.6233	0.4889	0.8272	0.054*
C12	0.9253 (3)	0.47759 (11)	0.7011 (3)	0.0469 (6)
H12	1.0114	0.4959	0.7004	0.056*
C24	0.3101 (3)	0.51017 (10)	0.6894 (3)	0.0426 (5)
H24	0.3203	0.5479	0.6577	0.051*
H2A	1.058 (4)	0.3631 (12)	0.183 (3)	0.051 (8)*
H4	0.557 (3)	0.3597 (11)	1.204 (3)	0.044 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0196 (6)	0.0549 (9)	0.0290 (7)	−0.0027 (6)	0.0040 (6)	−0.0056 (7)
N4	0.0200 (8)	0.0428 (9)	0.0267 (8)	0.0019 (7)	0.0021 (7)	−0.0066 (7)
O1	0.0200 (7)	0.0510 (9)	0.0342 (7)	0.0021 (6)	−0.0005 (6)	0.0048 (7)
C18	0.0228 (8)	0.0286 (8)	0.0231 (8)	−0.0006 (7)	0.0033 (8)	0.0014 (7)
N3	0.0334 (9)	0.0271 (7)	0.0230 (7)	−0.0028 (6)	0.0040 (7)	−0.0011 (6)
C5	0.0221 (9)	0.0259 (8)	0.0301 (9)	0.0001 (7)	0.0010 (8)	−0.0020 (8)
C4	0.0235 (9)	0.0258 (8)	0.0261 (9)	−0.0012 (7)	0.0017 (8)	−0.0031 (7)
N1	0.0292 (8)	0.0297 (8)	0.0263 (8)	0.0001 (7)	0.0027 (7)	0.0007 (7)
C3	0.0288 (9)	0.0297 (9)	0.0311 (10)	0.0050 (7)	−0.0019 (9)	−0.0038 (8)
C21	0.0216 (8)	0.0337 (10)	0.0276 (9)	0.0015 (7)	0.0028 (8)	−0.0002 (8)
C17	0.0246 (9)	0.0269 (8)	0.0249 (9)	−0.0021 (7)	0.0063 (8)	0.0023 (7)
N2	0.0220 (8)	0.0439 (10)	0.0315 (9)	0.0032 (7)	0.0047 (7)	0.0066 (8)
C7	0.0251 (10)	0.0390 (11)	0.0313 (9)	−0.0027 (8)	0.0067 (9)	−0.0027 (8)
C16	0.0296 (10)	0.0313 (9)	0.0307 (10)	0.0058 (8)	0.0091 (9)	0.0047 (8)
C25	0.0439 (12)	0.0329 (10)	0.0512 (13)	0.0004 (9)	−0.0023 (12)	−0.0046 (10)
C15	0.0473 (13)	0.0321 (9)	0.0339 (11)	0.0097 (9)	0.0157 (10)	0.0006 (9)
C8	0.0275 (9)	0.0339 (9)	0.0251 (8)	0.0022 (8)	0.0007 (8)	0.0024 (8)
C20	0.0309 (10)	0.0345 (10)	0.0260 (8)	−0.0067 (8)	0.0001 (8)	−0.0001 (8)
C19	0.0307 (11)	0.0574 (13)	0.0280 (10)	0.0063 (10)	0.0003 (9)	−0.0112 (9)
C11	0.0467 (13)	0.0429 (12)	0.0431 (12)	0.0042 (10)	−0.0025 (11)	−0.0125 (10)
C1	0.0455 (13)	0.0323 (10)	0.0287 (10)	0.0005 (9)	−0.0043 (10)	0.0017 (8)
C14	0.0493 (13)	0.0276 (10)	0.0265 (9)	0.0036 (9)	0.0080 (10)	−0.0031 (8)
C22	0.0370 (11)	0.0386 (11)	0.0260 (9)	0.0064 (9)	0.0037 (8)	−0.0001 (9)
C26	0.0419 (12)	0.0367 (10)	0.0325 (10)	−0.0014 (9)	−0.0046 (10)	−0.0030 (9)
C6	0.0376 (12)	0.0753 (17)	0.0362 (11)	0.0101 (12)	0.0077 (11)	0.0211 (12)
C9	0.0288 (10)	0.0461 (12)	0.0387 (11)	0.0016 (9)	0.0055 (10)	−0.0029 (10)
C2	0.0395 (11)	0.0315 (10)	0.0329 (10)	0.0082 (9)	−0.0063 (9)	−0.0026 (8)
C13	0.0272 (10)	0.0441 (11)	0.0421 (11)	−0.0009 (9)	0.0057 (10)	−0.0089 (10)
C23	0.0497 (14)	0.0452 (12)	0.0320 (10)	0.0104 (10)	0.0063 (11)	0.0113 (10)
C10	0.0369 (12)	0.0518 (14)	0.0454 (13)	0.0097 (10)	0.0050 (11)	−0.0117 (11)
C12	0.0347 (12)	0.0497 (13)	0.0563 (15)	−0.0080 (10)	0.0001 (12)	−0.0131 (12)
C24	0.0402 (12)	0.0340 (11)	0.0536 (13)	0.0057 (9)	0.0065 (11)	0.0103 (10)

Geometric parameters (Å, º) top

O3—C18	1.248 (2)	C15—C14	1.367 (4)
N4—C18	1.335 (3)	C15—H15	0.9500
N4—C19	1.450 (3)	C8—C13	1.386 (3)
N4—H4	0.87 (3)	C8—C9	1.390 (3)
O1—C5	1.243 (2)	C20—H20A	0.9900
C18—C17	1.469 (3)	C20—H20B	0.9900
N3—C14	1.364 (3)	C19—H19A	0.9800
N3—C17	1.378 (3)	C19—H19B	0.9800
N3—C20	1.475 (3)	C19—H19C	0.9800
C5—N2	1.334 (3)	C11—C10	1.373 (4)
C5—C4	1.475 (3)	C11—C12	1.376 (4)
C4—N1	1.386 (3)	C11—H11	0.9500
C4—C3	1.388 (3)	C1—C2	1.369 (3)
N1—C1	1.364 (3)	C1—H1	0.9500
N1—C7	1.463 (3)	C14—H14	0.9500
C3—C2	1.398 (3)	C22—C23	1.383 (3)
C3—H3	0.9500	C22—H22	0.9500
C21—C22	1.385 (3)	C26—H26	0.9500
C21—C26	1.391 (3)	C6—H6A	0.9800
C21—C20	1.515 (3)	C6—H6B	0.9800
C17—C16	1.389 (3)	C6—H6C	0.9800
N2—C6	1.456 (3)	C9—C10	1.385 (3)
N2—H2A	0.86 (4)	C9—H9	0.9500
C7—C8	1.513 (3)	C2—H2	0.9500
C7—H7A	0.9900	C13—C12	1.388 (3)
C7—H7B	0.9900	C13—H13	0.9500
C16—C15	1.408 (3)	C23—C24	1.383 (4)
C16—H16	0.9500	C23—H23	0.9500
C25—C24	1.381 (4)	C10—H10	0.9500
C25—C26	1.389 (3)	C12—H12	0.9500
C25—H25	0.9500	C24—H24	0.9500

C18—N4—C19	121.39 (18)	N3—C20—H20B	109.1
C18—N4—H4	120.7 (19)	C21—C20—H20B	109.1
C19—N4—H4	117.3 (19)	H20A—C20—H20B	107.8
O3—C18—N4	121.92 (18)	N4—C19—H19A	109.5
O3—C18—C17	121.96 (18)	N4—C19—H19B	109.5
N4—C18—C17	116.10 (17)	H19A—C19—H19B	109.5
C14—N3—C17	108.44 (18)	N4—C19—H19C	109.5
C14—N3—C20	122.93 (18)	H19A—C19—H19C	109.5
C17—N3—C20	127.76 (16)	H19B—C19—H19C	109.5
O1—C5—N2	122.4 (2)	C10—C11—C12	119.6 (2)
O1—C5—C4	122.11 (19)	C10—C11—H11	120.2
N2—C5—C4	115.51 (18)	C12—C11—H11	120.2
N1—C4—C3	107.17 (18)	N1—C1—C2	109.37 (19)
N1—C4—C5	123.61 (17)	N1—C1—H1	125.3
C3—C4—C5	128.74 (19)	C2—C1—H1	125.3
C1—N1—C4	108.33 (18)	N3—C14—C15	109.37 (19)
C1—N1—C7	122.91 (18)	N3—C14—H14	125.3
C4—N1—C7	127.97 (17)	C15—C14—H14	125.3
C4—C3—C2	108.07 (19)	C23—C22—C21	120.7 (2)
C4—C3—H3	126.0	C23—C22—H22	119.6
C2—C3—H3	126.0	C21—C22—H22	119.6
C22—C21—C26	118.8 (2)	C25—C26—C21	120.5 (2)
C22—C21—C20	120.01 (18)	C25—C26—H26	119.7
C26—C21—C20	121.14 (18)	C21—C26—H26	119.7
N3—C17—C16	107.72 (18)	N2—C6—H6A	109.5
N3—C17—C18	123.36 (17)	N2—C6—H6B	109.5
C16—C17—C18	128.44 (19)	H6A—C6—H6B	109.5
C5—N2—C6	122.00 (19)	N2—C6—H6C	109.5
C5—N2—H2A	119 (2)	H6A—C6—H6C	109.5
C6—N2—H2A	118 (2)	H6B—C6—H6C	109.5
N1—C7—C8	113.97 (17)	C10—C9—C8	120.8 (2)
N1—C7—H7A	108.8	C10—C9—H9	119.6
C8—C7—H7A	108.8	C8—C9—H9	119.6
N1—C7—H7B	108.8	C1—C2—C3	107.04 (19)
C8—C7—H7B	108.8	C1—C2—H2	126.5
H7A—C7—H7B	107.7	C3—C2—H2	126.5
C17—C16—C15	107.3 (2)	C8—C13—C12	120.6 (2)
C17—C16—H16	126.3	C8—C13—H13	119.7
C15—C16—H16	126.3	C12—C13—H13	119.7
C24—C25—C26	119.9 (2)	C24—C23—C22	120.1 (2)
C24—C25—H25	120.1	C24—C23—H23	120.0
C26—C25—H25	120.1	C22—C23—H23	120.0
C14—C15—C16	107.11 (19)	C11—C10—C9	120.3 (2)
C14—C15—H15	126.4	C11—C10—H10	119.8
C16—C15—H15	126.4	C9—C10—H10	119.8
C13—C8—C9	118.3 (2)	C11—C12—C13	120.4 (2)
C13—C8—C7	122.84 (19)	C11—C12—H12	119.8
C9—C8—C7	118.81 (19)	C13—C12—H12	119.8
N3—C20—C21	112.46 (16)	C25—C24—C23	119.9 (2)
N3—C20—H20A	109.1	C25—C24—H24	120.0
C21—C20—H20A	109.1	C23—C24—H24	120.0

C19—N4—C18—O3	10.3 (3)	N1—C7—C8—C9	−163.65 (18)
C19—N4—C18—C17	−168.55 (18)	C14—N3—C20—C21	−87.5 (2)
O1—C5—C4—N1	−20.5 (3)	C17—N3—C20—C21	80.6 (2)
N2—C5—C4—N1	161.67 (17)	C22—C21—C20—N3	107.6 (2)
O1—C5—C4—C3	150.5 (2)	C26—C21—C20—N3	−73.0 (3)
N2—C5—C4—C3	−27.3 (3)	C4—N1—C1—C2	−1.4 (2)
C3—C4—N1—C1	1.2 (2)	C7—N1—C1—C2	−171.95 (18)
C5—C4—N1—C1	173.90 (17)	C17—N3—C14—C15	1.3 (2)
C3—C4—N1—C7	171.15 (18)	C20—N3—C14—C15	171.34 (17)
C5—C4—N1—C7	−16.2 (3)	C16—C15—C14—N3	−0.9 (2)
N1—C4—C3—C2	−0.6 (2)	C26—C21—C22—C23	0.0 (3)
C5—C4—C3—C2	−172.77 (19)	C20—C21—C22—C23	179.4 (2)
C14—N3—C17—C16	−1.1 (2)	C24—C25—C26—C21	0.2 (4)
C20—N3—C17—C16	−170.53 (17)	C22—C21—C26—C25	0.1 (3)
C14—N3—C17—C18	−173.73 (17)	C20—C21—C26—C25	−179.3 (2)
C20—N3—C17—C18	16.8 (3)	C13—C8—C9—C10	0.3 (3)
O3—C18—C17—N3	18.7 (3)	C7—C8—C9—C10	−179.0 (2)
N4—C18—C17—N3	−162.52 (17)	N1—C1—C2—C3	1.0 (2)
O3—C18—C17—C16	−152.4 (2)	C4—C3—C2—C1	−0.2 (2)
N4—C18—C17—C16	26.4 (3)	C9—C8—C13—C12	0.4 (4)
O1—C5—N2—C6	−6.0 (3)	C7—C8—C13—C12	179.6 (2)
C4—C5—N2—C6	171.8 (2)	C21—C22—C23—C24	−0.4 (4)
C1—N1—C7—C8	75.4 (2)	C12—C11—C10—C9	0.3 (4)
C4—N1—C7—C8	−93.1 (2)	C8—C9—C10—C11	−0.6 (4)
N3—C17—C16—C15	0.5 (2)	C10—C11—C12—C13	0.4 (4)
C18—C17—C16—C15	172.66 (19)	C8—C13—C12—C11	−0.7 (4)
C17—C16—C15—C14	0.3 (2)	C26—C25—C24—C23	−0.7 (4)
N1—C7—C8—C13	17.1 (3)	C22—C23—C24—C25	0.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1ⁱ	0.87 (3)	2.04 (3)	2.869 (2)	161 (3)
N2—H2A···O3ⁱⁱ	0.86 (4)	2.10 (4)	2.902 (2)	154 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₄N₂O
M_r	214.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	110
a, b, c (Å)	9.8285 (18), 23.588 (4), 9.9230 (17)
β (°)	90.107 (3)
V (Å³)	2300.5 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.45 × 0.43 × 0.41

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.965, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	10728, 4879, 4388
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.640

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.157, 1.03
No. of reflections	4879
No. of parameters	300
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.32

Computer programs: SMART (Bruker,1999), SAINT-Plus (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1ⁱ	0.87 (3)	2.04 (3)	2.869 (2)	161 (3)
N2—H2A···O3ⁱⁱ	0.86 (4)	2.10 (4)	2.902 (2)	154 (3)

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

Acknowledgements

We thank the Natural Science Foundation of Guangdong Province, China (grant No. 06300581) for generous support of this study.

References

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