3-(1H-Benzotriazol-1-yl)-1-(3-methoxy­phen­yl)propan-1-one

Li, G.-J.; Hu, K.-C.

doi:10.1107/S1600536809004127

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o507

doi:10.1107/S1600536809004127

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3-(1H-Benzotriazol-1-yl)-1-(3-methoxyphenyl)propan-1-one

Guang-Jiu Li ^a and Kong-Cheng Hu ^a ^*

^aCollege of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, 210009 Nanjing, Jiangsu, People's Republic of China
^*Correspondence e-mail: hukongcheng@126.com

(Received 14 January 2009; accepted 4 February 2009; online 11 February 2009)

In the title molecule, C₁₆H₁₅N₃O₂, the benzotriazole fragment and the benzene ring form a dihedral angle of 75.02 (1)°. In the crystal structure, molecules related by translation along the a axis are linked into chains via weak C—H⋯π interactions.

Related literature

For the pharmacological activity of 1H-benzotriazole derivatives, see: Chen & Wu (2005 ). Some details of the synthesis have been described by Zhu et al. (2007 ). For reference values of geometric parameters in organic molecules, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₁₅N₃O₂
M_r = 281.31
Monoclinic, P 2₁ /c
a = 5.3583 (14) Å
b = 12.976 (4) Å
c = 19.688 (5) Å
β = 91.146 (4)°
V = 1368.6 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.21 × 0.15 × 0.07 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.981, T_max = 0.994
7461 measured reflections
2693 independent reflections
2279 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.112
S = 1.04
2693 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯Cg1ⁱ	0.97	2.74	3.504	136
Symmetry code: (i) x-1, y, z. Cg1 is the centroid of atoms C10–C15.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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, PARST (Nardelli, 1995 ) and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004127/cv2510sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809004127/cv2510Isup2.hkl

checkCIF report

Comment top

1H-Benzotriazole and its derivatives exhibit a broad spectrum of pharmacological activities, such as antifungal, antitumor and antineoplastic (Chen & Wu, 2005). In order to search for new benzotriazole derivatives with higher bioactivity, the title compound, (I), was synthesized and its structure is shown here.

In the title molecule (Fig. 1), all bond lengths and angles are within normal ranges (Allen et al., 1987). The benzotriazole system is almost planar with a dihedral angle of 1.45 (1)° between the triazole (N1–N3/C10/C11) and benzene (C10—C15) rings. The whole molecular is non-planar with a dihedral angle of 75.02 (1)° between the benzotriazole fragment and benzene C1–C6 ring. In the crystal, the molecules related by translation along axis a are linked into chains via the weak C—H···π interactions (Table 1).

Related literature top

For the pharmacological activity of 1H-benzotriazole derivatives, see: Chen & Wu (2005). Some details of the synthesis have been described by Zhu et al. (2007). For normal values of geometric parameters in organic molecules, see: Allen et al. (1987). Cg1 is the centroid of atoms C10–C15.

Experimental top

The title compound was prepared according to the literature method of Zhu et al.(2007). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution at room temperature over a period of one week.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top

Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids and the atom numbering scheme.

3-(1H-Benzotriazol-1-yl)-1-(3-methoxyphenyl)propan-1-one top

Crystal data top

C₁₆H₁₅N₃O₂	F(000) = 592
M_r = 281.31	D_x = 1.365 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.3583 (14) Å	Cell parameters from 3062 reflections
b = 12.976 (4) Å	θ = 2.6–25.9°
c = 19.688 (5) Å	µ = 0.09 mm⁻¹
β = 91.146 (4)°	T = 293 K
V = 1368.6 (6) Å³	Block, colourless
Z = 4	0.21 × 0.15 × 0.07 mm

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	2693 independent reflections
Radiation source: fine-focus sealed tube	2279 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
Detector resolution: 8.33 pixels mm^-1	θ_max = 26.0°, θ_min = 1.9°
ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −16→16
T_min = 0.981, T_max = 0.994	l = −24→17
7461 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0577P)² + 0.249P] where P = (F_o² + 2F_c²)/3
2693 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₆H₁₅N₃O₂	V = 1368.6 (6) Å³
M_r = 281.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.3583 (14) Å	µ = 0.09 mm⁻¹
b = 12.976 (4) Å	T = 293 K
c = 19.688 (5) Å	0.21 × 0.15 × 0.07 mm
β = 91.146 (4)°

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	2693 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2279 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.994	R_int = 0.018
7461 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.04	Δρ_max = 0.14 e Å⁻³
2693 reflections	Δρ_min = −0.23 e Å⁻³
190 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	0.2340 (2)	0.48618 (9)	0.09618 (6)	0.0607 (3)
O2	−0.2250 (2)	0.87656 (8)	−0.00231 (6)	0.0570 (3)
N1	0.0340 (2)	0.44726 (9)	0.23515 (6)	0.0427 (3)
C6	0.1036 (2)	0.64278 (10)	0.04534 (6)	0.0396 (3)
C2	−0.0452 (3)	0.80221 (11)	−0.00439 (7)	0.0444 (3)
C1	−0.0680 (3)	0.72307 (11)	0.04300 (7)	0.0428 (3)
H1A	−0.1990	0.7240	0.0733	0.051*
C10	0.2033 (2)	0.37083 (10)	0.24527 (7)	0.0390 (3)
C7	0.0797 (2)	0.55465 (11)	0.09372 (7)	0.0415 (3)
C5	0.3012 (3)	0.64292 (12)	0.00019 (7)	0.0462 (3)
H5A	0.4176	0.5898	0.0012	0.055*
C8	−0.1429 (3)	0.55249 (11)	0.13963 (7)	0.0458 (3)
H8A	−0.2938	0.5586	0.1119	0.055*
H8B	−0.1348	0.6120	0.1694	0.055*
N2	0.0569 (3)	0.51863 (10)	0.28486 (7)	0.0573 (4)
C12	0.5305 (3)	0.33871 (12)	0.32934 (8)	0.0541 (4)
H12A	0.6189	0.3565	0.3687	0.065*
C13	0.5867 (3)	0.25211 (13)	0.29353 (8)	0.0579 (4)
H13A	0.7178	0.2106	0.3087	0.070*
N3	0.2374 (3)	0.49148 (10)	0.32671 (7)	0.0589 (4)
C3	0.1519 (3)	0.80179 (12)	−0.04920 (7)	0.0498 (4)
H3B	0.1684	0.8543	−0.0810	0.060*
C11	0.3340 (3)	0.39961 (11)	0.30415 (7)	0.0440 (3)
C15	0.2589 (3)	0.28109 (11)	0.20939 (8)	0.0505 (4)
H15A	0.1686	0.2617	0.1706	0.061*
C4	0.3230 (3)	0.72214 (13)	−0.04583 (7)	0.0518 (4)
H4A	0.4562	0.7221	−0.0754	0.062*
C9	−0.1613 (3)	0.45603 (12)	0.18278 (8)	0.0516 (4)
H9A	−0.3224	0.4553	0.2044	0.062*
H9B	−0.1536	0.3962	0.1533	0.062*
C14	0.4524 (3)	0.22363 (12)	0.23434 (9)	0.0590 (4)
H14A	0.4972	0.1638	0.2116	0.071*
C16	−0.2412 (4)	0.94720 (13)	−0.05808 (9)	0.0621 (4)
H16A	−0.3743	0.9952	−0.0507	0.093*
H16B	−0.2738	0.9098	−0.0994	0.093*
H16C	−0.0865	0.9839	−0.0616	0.093*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0544 (6)	0.0619 (7)	0.0661 (7)	0.0170 (5)	0.0131 (5)	0.0130 (5)
O2	0.0617 (7)	0.0522 (6)	0.0572 (7)	0.0079 (5)	0.0049 (5)	0.0124 (5)
N1	0.0441 (6)	0.0438 (6)	0.0404 (6)	−0.0021 (5)	0.0016 (5)	0.0031 (5)
C6	0.0367 (7)	0.0471 (7)	0.0348 (7)	−0.0026 (6)	−0.0028 (5)	−0.0029 (5)
C2	0.0446 (8)	0.0454 (8)	0.0430 (8)	−0.0040 (6)	−0.0049 (6)	0.0004 (6)
C1	0.0406 (7)	0.0493 (8)	0.0386 (7)	−0.0021 (6)	0.0024 (6)	0.0005 (6)
C10	0.0389 (7)	0.0402 (7)	0.0381 (7)	−0.0062 (5)	0.0051 (5)	0.0047 (5)
C7	0.0368 (7)	0.0471 (8)	0.0405 (7)	0.0005 (6)	−0.0024 (5)	−0.0024 (6)
C5	0.0394 (7)	0.0570 (8)	0.0423 (8)	0.0010 (6)	0.0016 (6)	−0.0028 (6)
C8	0.0358 (7)	0.0545 (8)	0.0471 (8)	0.0020 (6)	0.0005 (6)	0.0077 (6)
N2	0.0683 (9)	0.0498 (7)	0.0537 (8)	0.0062 (6)	0.0001 (7)	−0.0052 (6)
C12	0.0559 (9)	0.0585 (9)	0.0476 (9)	−0.0050 (7)	−0.0089 (7)	0.0084 (7)
C13	0.0536 (9)	0.0557 (9)	0.0644 (10)	0.0074 (7)	−0.0007 (8)	0.0161 (8)
N3	0.0747 (9)	0.0522 (8)	0.0493 (8)	0.0034 (7)	−0.0080 (7)	−0.0087 (6)
C3	0.0522 (9)	0.0562 (9)	0.0409 (8)	−0.0107 (7)	−0.0002 (6)	0.0070 (6)
C11	0.0497 (8)	0.0437 (7)	0.0387 (7)	−0.0074 (6)	0.0006 (6)	0.0021 (6)
C15	0.0588 (9)	0.0473 (8)	0.0453 (8)	−0.0034 (7)	−0.0015 (7)	−0.0053 (6)
C4	0.0453 (8)	0.0683 (10)	0.0420 (8)	−0.0070 (7)	0.0079 (6)	0.0004 (7)
C9	0.0385 (8)	0.0610 (9)	0.0552 (9)	−0.0070 (7)	−0.0021 (6)	0.0119 (7)
C14	0.0703 (11)	0.0457 (8)	0.0613 (10)	0.0074 (8)	0.0072 (8)	−0.0018 (7)
C16	0.0732 (11)	0.0537 (9)	0.0591 (10)	0.0047 (8)	−0.0062 (8)	0.0119 (8)

Geometric parameters (Å, º) top

O1—C7	1.2137 (17)	C8—H8B	0.9700
O2—C2	1.3649 (18)	N2—N3	1.3063 (19)
O2—C16	1.4316 (18)	C12—C13	1.363 (2)
N1—N2	1.3511 (17)	C12—C11	1.399 (2)
N1—C10	1.3563 (17)	C12—H12A	0.9300
N1—C9	1.4586 (18)	C13—C14	1.407 (2)
C6—C1	1.3896 (19)	C13—H13A	0.9300
C6—C5	1.3961 (19)	N3—C11	1.3769 (19)
C6—C7	1.4954 (19)	C3—C4	1.382 (2)
C2—C3	1.389 (2)	C3—H3B	0.9300
C2—C1	1.394 (2)	C15—C14	1.361 (2)
C1—H1A	0.9300	C15—H15A	0.9300
C10—C11	1.3933 (19)	C4—H4A	0.9300
C10—C15	1.397 (2)	C9—H9A	0.9700
C7—C8	1.511 (2)	C9—H9B	0.9700
C5—C4	1.377 (2)	C14—H14A	0.9300
C5—H5A	0.9300	C16—H16A	0.9600
C8—C9	1.517 (2)	C16—H16B	0.9600
C8—H8A	0.9700	C16—H16C	0.9600

C2—O2—C16	117.48 (12)	C12—C13—C14	122.05 (15)
N2—N1—C10	110.12 (12)	C12—C13—H13A	119.0
N2—N1—C9	120.80 (12)	C14—C13—H13A	119.0
C10—N1—C9	128.99 (12)	N2—N3—C11	107.97 (12)
C1—C6—C5	119.18 (13)	C4—C3—C2	118.97 (13)
C1—C6—C7	121.97 (12)	C4—C3—H3B	120.5
C5—C6—C7	118.83 (12)	C2—C3—H3B	120.5
O2—C2—C3	124.61 (13)	N3—C11—C10	108.32 (13)
O2—C2—C1	115.41 (13)	N3—C11—C12	131.29 (14)
C3—C2—C1	119.98 (14)	C10—C11—C12	120.37 (14)
C6—C1—C2	120.50 (13)	C14—C15—C10	116.26 (14)
C6—C1—H1A	119.7	C14—C15—H15A	121.9
C2—C1—H1A	119.7	C10—C15—H15A	121.9
N1—C10—C11	104.48 (12)	C5—C4—C3	121.66 (14)
N1—C10—C15	133.14 (13)	C5—C4—H4A	119.2
C11—C10—C15	122.38 (13)	C3—C4—H4A	119.2
O1—C7—C6	121.22 (12)	N1—C9—C8	113.99 (12)
O1—C7—C8	120.51 (13)	N1—C9—H9A	108.8
C6—C7—C8	118.28 (12)	C8—C9—H9A	108.8
C4—C5—C6	119.69 (14)	N1—C9—H9B	108.8
C4—C5—H5A	120.2	C8—C9—H9B	108.8
C6—C5—H5A	120.2	H9A—C9—H9B	107.7
C7—C8—C9	114.27 (12)	C15—C14—C13	121.90 (15)
C7—C8—H8A	108.7	C15—C14—H14A	119.0
C9—C8—H8A	108.7	C13—C14—H14A	119.0
C7—C8—H8B	108.7	O2—C16—H16A	109.5
C9—C8—H8B	108.7	O2—C16—H16B	109.5
H8A—C8—H8B	107.6	H16A—C16—H16B	109.5
N3—N2—N1	109.11 (12)	O2—C16—H16C	109.5
C13—C12—C11	117.02 (15)	H16A—C16—H16C	109.5
C13—C12—H12A	121.5	H16B—C16—H16C	109.5
C11—C12—H12A	121.5

C16—O2—C2—C3	13.0 (2)	N1—N2—N3—C11	−0.44 (17)
C16—O2—C2—C1	−167.35 (13)	O2—C2—C3—C4	179.60 (13)
C5—C6—C1—C2	0.8 (2)	C1—C2—C3—C4	0.0 (2)
C7—C6—C1—C2	−177.70 (12)	N2—N3—C11—C10	0.20 (17)
O2—C2—C1—C6	179.60 (12)	N2—N3—C11—C12	178.69 (15)
C3—C2—C1—C6	−0.8 (2)	N1—C10—C11—N3	0.12 (15)
N2—N1—C10—C11	−0.40 (14)	C15—C10—C11—N3	179.28 (13)
C9—N1—C10—C11	−176.92 (12)	N1—C10—C11—C12	−178.56 (12)
N2—N1—C10—C15	−179.42 (15)	C15—C10—C11—C12	0.6 (2)
C9—N1—C10—C15	4.1 (2)	C13—C12—C11—N3	−177.86 (15)
C1—C6—C7—O1	−178.41 (13)	C13—C12—C11—C10	0.5 (2)
C5—C6—C7—O1	3.1 (2)	N1—C10—C15—C14	177.59 (14)
C1—C6—C7—C8	1.83 (19)	C11—C10—C15—C14	−1.3 (2)
C5—C6—C7—C8	−176.67 (12)	C6—C5—C4—C3	−0.7 (2)
C1—C6—C5—C4	−0.1 (2)	C2—C3—C4—C5	0.7 (2)
C7—C6—C5—C4	178.46 (13)	N2—N1—C9—C8	61.53 (17)
O1—C7—C8—C9	−4.4 (2)	C10—N1—C9—C8	−122.27 (15)
C6—C7—C8—C9	175.40 (12)	C7—C8—C9—N1	68.40 (17)
C10—N1—N2—N3	0.54 (16)	C10—C15—C14—C13	1.0 (2)
C9—N1—N2—N3	177.39 (12)	C12—C13—C14—C15	0.1 (3)
C11—C12—C13—C14	−0.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···Cg1ⁱ	0.97	2.74	3.504	136

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅N₃O₂
M_r	281.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	5.3583 (14), 12.976 (4), 19.688 (5)
β (°)	91.146 (4)
V (Å³)	1368.6 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.21 × 0.15 × 0.07

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.981, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	7461, 2693, 2279
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.112, 1.04
No. of reflections	2693
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.23

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···Cg1ⁱ	0.97	2.743	3.504	135.79

Symmetry code: (i) x−1, y, z.

Acknowledgements

This project was supported by the Natural Science Foundation of Shandong Province (grant Nos. Y2008B02 and Y2008B32).

References

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Chen, Z.-Y. & Wu, M.-T. (2005). Org. Lett. 7, 475–477. Web of Science CrossRef PubMed CAS Google Scholar
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