4-[(Z)-Allyl­amino­(phen­yl)methyl­ene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Xu, H.-Z.; Yang, Y.-X.; Yan, J.; Zhu, Y.-Q.

doi:10.1107/S160053681001384X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1309

https://doi.org/10.1107/S160053681001384X

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4-[(Z)-Allylamino(phenyl)methylene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Hai-Zhen Xu,^a ^* Yan-Xia Yang,^b Jing Yan ^a and You-Quan Zhu ^c ^*

^aCollege of Chemistry, Tianjin Normal University, 393 Binshuixi Road, Xiqing District, Tianjin 300387, People's Republic of China, ^bNankai High School, 100 Sima Road, Nankai District, Tianjin 300100, People's Republic of China, and ^cState Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China
^*Correspondence e-mail: hsxyxhz@mail.tjnu.edu.cn, zyq8165@nankai.edu.cn

(Received 5 April 2010; accepted 14 April 2010; online 12 May 2010)

The title compound, C₂₀H₁₉N₃O, exists in a keto–enamine tautomeric form. The pyrazolone ring makes dihedral angles of 20.52 (10) and 77.73 (5)° with the two phenyl rings and an intramolecular N—H⋯O hydrogen bond occurs. A weak intermolecular C—H⋯O hydrogen bond is observed in the crystal structure. The allyl group is disordered over two positions, with site-occupancy factors of 0.533 (5) and 0.467 (5).

Related literature

For the analgesic activity of metal complexes with 1-phenyl-3-methyl-4-benzoylpyrazolon-5-one, see: Li et al. (1997 ); Liu et al. (1980 ); Zhou et al. (1999 ). For related structures, see: Bao et al. (2004 ); Sun et al. (2007 ); Zhu et al. (2005 ).

Experimental

Crystal data

C₂₀H₁₉N₃O
M_r = 317.38
Triclinic, $[P \overline 1]$
a = 9.295 (1) Å
b = 9.8440 (12) Å
c = 10.0670 (14) Å
α = 86.175 (8)°
β = 89.280 (9)°
γ = 74.329 (7)°
V = 884.90 (19) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.22 × 0.18 × 0.16 mm

Data collection

Rigaku Saturn724 CCD camera diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2009 ) T_min = 0.984, T_max = 0.988
10726 measured reflections
3910 independent reflections
2135 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.133
S = 0.94
3910 reflections
242 parameters
16 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1	1.06 (2)	1.75 (2)	2.687 (2)	145 (2)
C17—H17⋯O1ⁱ	0.95	2.41	3.345 (2)	168
Symmetry code: (i) -x, -y+2, -z+2.

Data collection: CrystalClear (Rigaku, 2009); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2009); software used to prepare material for publication: CrystalStructure.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681001384X/is2538sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681001384X/is2538Isup2.hkl

checkCIF report

Comment top

1-Phenyl-3-methyl-4-benzoylpyrazolon-5-one (HPMBP), an effective β-diketonate, is widely used and well known for its extractive ability. In recent years, HPMBP and its metal complexes have also been found to have good antibacterial and biological properties. Its metal complexes have analgesic activity (Liu et al., 1980; Li et al., 1997; Zhou et al., 1999). In order to develop new medicines, we have synthesized the title compound, (I), and its structure is reported here.

The structure of (I) is shown in Fig. 1. The dihedral angles formed by the pyrazolone ring with the two phenyl rings C5–C10 and C12–C17 are 20.52 (10) and 77.73 (5)°, respectively. The O atom of the 3-methyl-1-phenylpyrazol-5-one moiety and the N atom of the allylamino group are available for coordination with metals. The pyrazole ring is planar and atoms O1, C1, C2, C11 and N3 are almost coplanar, the largest deviation being 0.0195 (11) Å for atom C11. The dihedral angle between this mean plane and the pyrazoline ring of PMBP is 2.01 (12)°. The bond lengths within this part of the molecule lie between classical single- and double-bond lengths, indicating extensive conjugation. A strong intramolecular N3—H3···O1 hydrogen bond (Table 1) is observed, leading to a keto-enamine form. The crystal structure includes intermolecular C—H···O hydrogen bonds (Table 1 and Fig. 2).

Related literature top

For the analgesic activity of metal complexes with 1-phenyl-3-methyl-4-benzoylpyrazolon-5-one, see: Li et al. (1997); Liu et al. (1980); Zhou et al. (1999). For related structures, see: Bao et al. (2004); Sun et al. (2007); Zhu et al. (2005).

Experimental top

Compound (I) was synthesized by refluxing a mixture of 1-phenyl-3-methyl-4-benzoylpyrazol-5-one (10 mmol) and allylamine (10 mmol) in ethanol (80 ml) over a steam bath for about 10 h. Excess solvent was removed by evaporation and the solution was cooled to room temperature. After 4 d, a colorless solid was obtained and this was dried in air. The product was recrystallized from ethanol, to afford colorless crystals of (I) suitable for X-ray analysis.

Structure description top

For the analgesic activity of metal complexes with 1-phenyl-3-methyl-4-benzoylpyrazolon-5-one, see: Li et al. (1997); Liu et al. (1980); Zhou et al. (1999). For related structures, see: Bao et al. (2004); Sun et al. (2007); Zhu et al. (2005).

Computing details top

Data collection: CrystalClear (Rigaku, 2009); cell refinement: CrystalClear (Rigaku, 2009); data reduction: CrystalClear (Rigaku, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2009); software used to prepare material for publication: CrystalStructure (Rigaku, 2009).

Figures top

	Fig. 1. View of the title compound, with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Intermolecular hydrogen bonds (dashed line) in the structure of (I).

4-[(Z)-Allylamino(phenyl)methylene]-3-methyl-1-phenyl- 1H-pyrazol-5(4H)-one top

Crystal data top

C₂₀H₁₉N₃O	Z = 2
M_r = 317.38	F(000) = 336
Triclinic, P1	D_x = 1.191 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 9.295 (1) Å	Cell parameters from 2516 reflections
b = 9.8440 (12) Å	θ = 2.0–27.2°
c = 10.0670 (14) Å	µ = 0.08 mm⁻¹
α = 86.175 (8)°	T = 293 K
β = 89.280 (9)°	Prism, colorless
γ = 74.329 (7)°	0.22 × 0.18 × 0.16 mm
V = 884.90 (19) Å³

Data collection top

Rigaku Saturn724 CCD camera diffractometer	3910 independent reflections
Radiation source: rotating anode	2135 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.032
ω scans	θ_max = 27.2°, θ_min = 2.0°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2009)	h = −11→11
T_min = 0.984, T_max = 0.988	k = −12→12
10726 measured reflections	l = −12→12

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)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.133	w = 1/[σ²(F_o²) + (0.0682P)²] where P = (F_o² + 2F_c²)/3
S = 0.94	(Δ/σ)_max < 0.001
3910 reflections	Δρ_max = 0.17 e Å⁻³
242 parameters	Δρ_min = −0.19 e Å⁻³
16 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: 0.044 (6)

Crystal data top

C₂₀H₁₉N₃O	γ = 74.329 (7)°
M_r = 317.38	V = 884.90 (19) Å³
Triclinic, P1	Z = 2
a = 9.295 (1) Å	Mo Kα radiation
b = 9.8440 (12) Å	µ = 0.08 mm⁻¹
c = 10.0670 (14) Å	T = 293 K
α = 86.175 (8)°	0.22 × 0.18 × 0.16 mm
β = 89.280 (9)°

Data collection top

Rigaku Saturn724 CCD camera diffractometer	3910 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2009)	2135 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.988	R_int = 0.032
10726 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	16 restraints
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	Δρ_max = 0.17 e Å⁻³
3910 reflections	Δρ_min = −0.19 e Å⁻³
242 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	Occ. (<1)
O1	0.20365 (11)	0.99841 (12)	0.85524 (11)	0.0659 (4)
N1	0.08977 (14)	1.17446 (14)	0.69281 (13)	0.0581 (4)
N2	−0.03759 (15)	1.20734 (14)	0.61172 (14)	0.0623 (4)
N3	0.04161 (16)	0.81085 (15)	0.89396 (14)	0.0668 (4)
H3	0.130 (2)	0.858 (2)	0.9078 (19)	0.098 (6)*
C1	0.10280 (17)	1.05164 (17)	0.77140 (15)	0.0532 (4)
C2	−0.02439 (16)	1.00449 (16)	0.73734 (15)	0.0523 (4)
C3	−0.10420 (17)	1.10712 (17)	0.63795 (16)	0.0570 (4)
C4	−0.2423 (2)	1.1118 (2)	0.56172 (19)	0.0750 (5)
H4A	−0.2771	1.2037	0.5118	0.090*
H4B	−0.3202	1.0983	0.6237	0.090*
H4C	−0.2203	1.0364	0.4996	0.090*
C5	0.17910 (19)	1.27022 (17)	0.69264 (16)	0.0593 (4)
C6	0.1197 (2)	1.40867 (19)	0.64376 (18)	0.0724 (5)
H6	0.0188	1.4392	0.6140	0.087*
C7	0.2068 (3)	1.5026 (2)	0.6381 (2)	0.0905 (7)
H7	0.1662	1.5972	0.6031	0.109*
C8	0.3519 (3)	1.4595 (2)	0.6831 (2)	0.0945 (7)
H8	0.4120	1.5238	0.6788	0.113*
C9	0.4100 (2)	1.3225 (2)	0.7344 (2)	0.0852 (6)
H9	0.5097	1.2934	0.7674	0.102*
C10	0.3249 (2)	1.2272 (2)	0.73843 (19)	0.0716 (5)
H10	0.3664	1.1325	0.7725	0.086*
C11	−0.05472 (16)	0.88577 (16)	0.80315 (15)	0.0531 (4)
C12	−0.19394 (17)	0.84403 (16)	0.77922 (16)	0.0536 (4)
C13	−0.2147 (2)	0.77965 (19)	0.66608 (18)	0.0703 (5)
H13	−0.1366	0.7554	0.6029	0.084*
C14	−0.3499 (2)	0.7506 (2)	0.6453 (2)	0.0828 (6)
H14	−0.3645	0.7065	0.5674	0.099*
C15	−0.4624 (2)	0.7848 (2)	0.7356 (2)	0.0779 (6)
H15	−0.5556	0.7662	0.7197	0.093*
C16	−0.44114 (19)	0.8458 (2)	0.8489 (2)	0.0732 (5)
H16	−0.5192	0.8681	0.9122	0.088*
C17	−0.30750 (18)	0.87516 (18)	0.87209 (17)	0.0642 (5)
H17	−0.2931	0.9167	0.9516	0.077*
C18	0.0316 (2)	0.68276 (19)	0.9706 (2)	0.0775 (6)
H18A	−0.0194	0.6319	0.9183	0.093*	0.533 (9)
H18B	−0.0251	0.7075	1.0499	0.093*	0.533 (9)
H18C	0.0338	0.6098	0.9113	0.093*	0.467 (9)
H18D	−0.0616	0.7019	1.0174	0.093*	0.467 (9)
C19	0.1772 (5)	0.5941 (6)	1.0070 (7)	0.0726 (16)	0.533 (9)
H19	0.2349	0.5531	0.9340	0.087*	0.533 (9)
C20	0.2430 (9)	0.5605 (8)	1.1187 (6)	0.106 (2)	0.533 (9)
H20A	0.1939	0.5966	1.1973	0.128*	0.533 (9)
H20B	0.3415	0.4993	1.1237	0.128*	0.533 (9)
C19'	0.1553 (8)	0.6368 (9)	1.0669 (8)	0.098 (2)	0.467 (9)
H19'	0.1399	0.6733	1.1525	0.118*	0.467 (9)
C20'	0.2789 (10)	0.5535 (13)	1.0447 (12)	0.178 (4)	0.467 (9)
H20C	0.2984	0.5148	0.9602	0.214*	0.467 (9)
H20D	0.3537	0.5286	1.1122	0.214*	0.467 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0607 (7)	0.0729 (8)	0.0680 (8)	−0.0270 (6)	−0.0173 (6)	0.0090 (6)
N1	0.0619 (8)	0.0603 (8)	0.0555 (8)	−0.0236 (7)	−0.0107 (7)	0.0028 (7)
N2	0.0655 (9)	0.0643 (9)	0.0591 (9)	−0.0222 (7)	−0.0147 (7)	0.0036 (7)
N3	0.0652 (9)	0.0676 (9)	0.0717 (10)	−0.0284 (7)	−0.0162 (8)	0.0144 (8)
C1	0.0540 (9)	0.0574 (10)	0.0496 (9)	−0.0171 (7)	−0.0043 (8)	−0.0023 (8)
C2	0.0510 (9)	0.0576 (9)	0.0503 (9)	−0.0184 (7)	−0.0055 (7)	−0.0023 (8)
C3	0.0556 (9)	0.0645 (10)	0.0520 (10)	−0.0176 (8)	−0.0064 (8)	−0.0032 (8)
C4	0.0705 (12)	0.0822 (13)	0.0747 (13)	−0.0268 (10)	−0.0227 (10)	0.0081 (10)
C5	0.0696 (11)	0.0620 (11)	0.0527 (10)	−0.0284 (9)	−0.0022 (8)	−0.0043 (8)
C6	0.0852 (13)	0.0670 (12)	0.0705 (12)	−0.0303 (10)	−0.0113 (10)	0.0000 (9)
C7	0.1128 (17)	0.0687 (13)	0.0989 (17)	−0.0404 (12)	−0.0136 (14)	−0.0006 (11)
C8	0.1163 (18)	0.0822 (15)	0.1049 (18)	−0.0598 (14)	−0.0044 (14)	−0.0092 (13)
C9	0.0827 (13)	0.0890 (15)	0.0965 (16)	−0.0437 (11)	−0.0090 (12)	−0.0093 (12)
C10	0.0711 (12)	0.0700 (12)	0.0800 (13)	−0.0302 (9)	−0.0061 (10)	−0.0027 (10)
C11	0.0518 (9)	0.0589 (10)	0.0496 (9)	−0.0162 (8)	−0.0045 (7)	−0.0047 (8)
C12	0.0554 (9)	0.0572 (9)	0.0509 (9)	−0.0201 (7)	−0.0051 (8)	−0.0015 (7)
C13	0.0753 (12)	0.0874 (13)	0.0586 (11)	−0.0371 (10)	0.0013 (9)	−0.0164 (10)
C14	0.0929 (14)	0.1009 (15)	0.0694 (13)	−0.0478 (12)	−0.0109 (11)	−0.0197 (11)
C15	0.0674 (12)	0.0878 (14)	0.0875 (15)	−0.0360 (10)	−0.0143 (11)	−0.0044 (12)
C16	0.0557 (10)	0.0876 (13)	0.0795 (13)	−0.0234 (9)	−0.0013 (9)	−0.0108 (11)
C17	0.0580 (10)	0.0765 (12)	0.0617 (11)	−0.0218 (8)	−0.0027 (9)	−0.0140 (9)
C18	0.0852 (13)	0.0719 (12)	0.0779 (13)	−0.0302 (10)	−0.0147 (11)	0.0179 (10)
C19	0.052 (3)	0.067 (3)	0.092 (4)	−0.005 (2)	−0.003 (3)	−0.001 (3)
C20	0.095 (4)	0.118 (4)	0.093 (4)	−0.012 (3)	−0.024 (3)	0.029 (3)
C19'	0.123 (6)	0.092 (5)	0.059 (4)	0.006 (4)	0.005 (4)	0.000 (3)
C20'	0.115 (6)	0.273 (9)	0.110 (7)	0.013 (6)	−0.002 (5)	−0.025 (6)

Geometric parameters (Å, º) top

O1—C1	1.2494 (17)	C11—C12	1.487 (2)
N1—C1	1.378 (2)	C12—C13	1.380 (2)
N1—N2	1.3981 (17)	C12—C17	1.386 (2)
N1—C5	1.4145 (19)	C13—C14	1.383 (2)
N2—C3	1.3106 (19)	C13—H13	0.9500
N3—C11	1.3249 (19)	C14—C15	1.364 (3)
N3—C18	1.458 (2)	C14—H14	0.9500
N3—H3	1.062 (19)	C15—C16	1.364 (3)
C1—C2	1.435 (2)	C15—H15	0.9500
C2—C11	1.398 (2)	C16—C17	1.375 (2)
C2—C3	1.432 (2)	C16—H16	0.9500
C3—C4	1.492 (2)	C17—H17	0.9500
C4—H4A	0.9800	C18—C19	1.436 (5)
C4—H4B	0.9800	C18—C19'	1.468 (6)
C4—H4C	0.9800	C18—H18A	0.9601
C5—C10	1.382 (2)	C18—H18B	0.9600
C5—C6	1.384 (2)	C18—H18C	0.9600
C6—C7	1.382 (3)	C18—H18D	0.9600
C6—H6	0.9500	C19—C20	1.267 (7)
C7—C8	1.373 (3)	C19—H19	0.9500
C7—H7	0.9500	C20—H20A	0.9500
C8—C9	1.378 (3)	C20—H20B	0.9500
C8—H8	0.9500	C19'—C20'	1.246 (8)
C9—C10	1.379 (2)	C19'—H19'	0.9500
C9—H9	0.9500	C20'—H20C	0.9500
C10—H10	0.9500	C20'—H20D	0.9500

C1—N1—N2	111.74 (12)	C13—C12—C17	119.47 (15)
C1—N1—C5	128.86 (14)	C13—C12—C11	122.02 (15)
N2—N1—C5	119.21 (13)	C17—C12—C11	118.47 (14)
C3—N2—N1	106.53 (13)	C12—C13—C14	119.53 (18)
C11—N3—C18	126.82 (15)	C12—C13—H13	120.2
C11—N3—H3	110.9 (10)	C14—C13—H13	120.2
C18—N3—H3	122.3 (10)	C15—C14—C13	120.61 (18)
O1—C1—N1	125.78 (15)	C15—C14—H14	119.7
O1—C1—C2	129.30 (15)	C13—C14—H14	119.7
N1—C1—C2	104.91 (13)	C16—C15—C14	119.97 (18)
C11—C2—C3	132.68 (15)	C16—C15—H15	120.0
C11—C2—C1	121.72 (14)	C14—C15—H15	120.0
C3—C2—C1	105.45 (13)	C15—C16—C17	120.51 (18)
N2—C3—C2	111.37 (14)	C15—C16—H16	119.7
N2—C3—C4	118.53 (15)	C17—C16—H16	119.7
C2—C3—C4	130.07 (15)	C16—C17—C12	119.87 (16)
C3—C4—H4A	109.5	C16—C17—H17	120.1
C3—C4—H4B	109.5	C12—C17—H17	120.1
H4A—C4—H4B	109.5	C19—C18—N3	111.1 (3)
C3—C4—H4C	109.5	N3—C18—C19'	110.1 (4)
H4A—C4—H4C	109.5	C19—C18—H18A	109.6
H4B—C4—H4C	109.5	N3—C18—H18A	109.1
C10—C5—C6	119.66 (17)	C19—C18—H18B	109.0
C10—C5—N1	121.11 (15)	N3—C18—H18B	109.6
C6—C5—N1	119.23 (16)	H18A—C18—H18B	108.3
C7—C6—C5	120.17 (19)	N3—C18—H18C	109.6
C7—C6—H6	119.9	C19'—C18—H18C	110.4
C5—C6—H6	119.9	N3—C18—H18D	109.1
C8—C7—C6	120.1 (2)	C19'—C18—H18D	109.3
C8—C7—H7	120.0	H18C—C18—H18D	108.3
C6—C7—H7	120.0	C20—C19—C18	131.8 (9)
C7—C8—C9	119.77 (19)	C20—C19—H19	114.1
C7—C8—H8	120.1	C18—C19—H19	114.1
C9—C8—H8	120.1	C19—C20—H20A	120.0
C8—C9—C10	120.6 (2)	C19—C20—H20B	120.0
C8—C9—H9	119.7	H20A—C20—H20B	120.0
C10—C9—H9	119.7	C20'—C19'—C18	124.8 (11)
C9—C10—C5	119.68 (18)	C20'—C19'—H19'	117.6
C9—C10—H10	120.2	C18—C19'—H19'	117.6
C5—C10—H10	120.2	C19'—C20'—H20C	120.0
N3—C11—C2	118.69 (14)	C19'—C20'—H20D	120.0
N3—C11—C12	118.78 (14)	H20C—C20'—H20D	120.0
C2—C11—C12	122.48 (14)

C1—N1—N2—C3	−0.16 (18)	C8—C9—C10—C5	−1.2 (3)
C5—N1—N2—C3	−175.66 (13)	C6—C5—C10—C9	−0.3 (3)
N2—N1—C1—O1	−178.45 (15)	N1—C5—C10—C9	178.70 (16)
C5—N1—C1—O1	−3.5 (3)	C18—N3—C11—C2	−178.50 (16)
N2—N1—C1—C2	0.05 (17)	C18—N3—C11—C12	4.1 (3)
C5—N1—C1—C2	175.00 (15)	C3—C2—C11—N3	−178.88 (16)
O1—C1—C2—C11	2.3 (3)	C1—C2—C11—N3	−3.9 (2)
N1—C1—C2—C11	−176.11 (14)	C3—C2—C11—C12	−1.5 (3)
O1—C1—C2—C3	178.50 (16)	C1—C2—C11—C12	173.46 (14)
N1—C1—C2—C3	0.07 (16)	N3—C11—C12—C13	−106.78 (19)
N1—N2—C3—C2	0.21 (18)	C2—C11—C12—C13	75.9 (2)
N1—N2—C3—C4	−177.88 (14)	N3—C11—C12—C17	75.2 (2)
C11—C2—C3—N2	175.40 (17)	C2—C11—C12—C17	−102.11 (19)
C1—C2—C3—N2	−0.18 (18)	C17—C12—C13—C14	1.7 (3)
C11—C2—C3—C4	−6.8 (3)	C11—C12—C13—C14	−176.21 (16)
C1—C2—C3—C4	177.63 (16)	C12—C13—C14—C15	−0.1 (3)
C1—N1—C5—C10	24.4 (3)	C13—C14—C15—C16	−1.2 (3)
N2—N1—C5—C10	−161.01 (15)	C14—C15—C16—C17	1.0 (3)
C1—N1—C5—C6	−156.64 (16)	C15—C16—C17—C12	0.7 (3)
N2—N1—C5—C6	18.0 (2)	C13—C12—C17—C16	−2.0 (3)
C10—C5—C6—C7	1.4 (3)	C11—C12—C17—C16	176.02 (15)
N1—C5—C6—C7	−177.61 (17)	C11—N3—C18—C19	151.5 (4)
C5—C6—C7—C8	−1.1 (3)	C11—N3—C18—C19'	−176.4 (4)
C6—C7—C8—C9	−0.4 (3)	N3—C18—C19—C20	111.7 (6)
C7—C8—C9—C10	1.5 (3)	N3—C18—C19'—C20'	−90.6 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	1.06 (2)	1.75 (2)	2.687 (2)	145 (2)
C17—H17···O1ⁱ	0.95	2.41	3.345 (2)	168

Symmetry code: (i) −x, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉N₃O
M_r	317.38
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.295 (1), 9.8440 (12), 10.0670 (14)
α, β, γ (°)	86.175 (8), 89.280 (9), 74.329 (7)
V (Å³)	884.90 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.22 × 0.18 × 0.16

Data collection
Diffractometer	Rigaku Saturn724 CCD camera
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2009)
T_min, T_max	0.984, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	10726, 3910, 2135
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.644

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.133, 0.94
No. of reflections	3910
No. of parameters	242
No. of restraints	16
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.19

Computer programs: CrystalClear (Rigaku, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	1.06 (2)	1.75 (2)	2.687 (2)	145 (2)
C17—H17···O1ⁱ	0.95	2.41	3.345 (2)	168

Symmetry code: (i) −x, −y+2, −z+2.

Acknowledgements

The authors gratefully acknowledge the financial support of the National Natural Science Foundation of China (grant No. 20772066).

References

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