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

In the title compound, C₁₆H₁₅N₃O₂, the dihedral angle between the benzotriazole unit and the other benzene ring is 79.06 (1)°. The crystal structure is stabilized by C—H...π inter­actions and van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• R factor = 0.042
• wR factor = 0.117
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

3-(1H-Benzotriazol-1-yl)-1-(4-methoxyphenyl)propan-1-one

Crystal data

C16H15N3O2	F(000) = 592
Mr = 281.31	Dx = 1.320 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 2043 reflections
a = 10.0442 (17) Å	θ = 2.5–25.3°
b = 9.7562 (17) Å	µ = 0.09 mm^−1
c = 14.443 (2) Å	T = 293 K
β = 90.254 (3)°	Plate, colourless
V = 1415.3 (4) Å^3	0.25 × 0.19 × 0.05 mm
Z = 4

Data collection

Siemens SMART 1000 CCD area detector diffractometer	2783 independent reflections
Radiation source: fine-focus sealed tube	1979 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 8.33 pixels mm^-1	θmax = 26.0°, θmin = 2.0°
ω scans	h = −12→12
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	k = −12→12
Tmin = 0.978, Tmax = 0.996	l = −17→11
7734 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0548P)^2 + 0.141P] where P = (Fo^2 + 2Fc^2)/3
2783 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.13 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C6	0.03114 (14)	0.12595 (15)	0.12079 (10)	0.0497 (4)
C1	0.03160 (15)	−0.01709 (16)	0.12029 (10)	0.0524 (4)
H1A	0.1119	−0.0645	0.1189	0.063*
O1	0.26491 (11)	0.13480 (12)	0.10726 (9)	0.0741 (4)
N1	0.32820 (12)	0.41992 (13)	0.00474 (10)	0.0584 (4)
C7	0.16168 (15)	0.19812 (16)	0.11582 (10)	0.0542 (4)
C2	−0.08680 (15)	−0.08802 (16)	0.12185 (11)	0.0591 (4)
O2	−0.09795 (12)	−0.22712 (13)	0.12033 (10)	0.0876 (4)
C15	0.41170 (14)	0.34106 (15)	−0.04681 (11)	0.0541 (4)
C5	−0.08899 (15)	0.19570 (17)	0.12429 (11)	0.0592 (4)
H5A	−0.0901	0.2910	0.1253	0.071*
C8	0.16324 (16)	0.35242 (17)	0.12261 (12)	0.0645 (5)
H8A	0.1351	0.3787	0.1843	0.077*
H8B	0.0989	0.3892	0.0790	0.077*
C10	0.39872 (15)	0.39235 (16)	−0.13559 (12)	0.0598 (4)
C3	−0.20662 (16)	−0.01712 (19)	0.12506 (12)	0.0672 (5)
H3A	−0.2867	−0.0650	0.1263	0.081*
C4	−0.20690 (16)	0.12305 (19)	0.12635 (12)	0.0676 (5)
H4A	−0.2874	0.1700	0.1286	0.081*
N2	0.26816 (15)	0.51443 (14)	−0.04968 (12)	0.0729 (4)
N3	0.30924 (16)	0.49966 (15)	−0.13462 (12)	0.0759 (4)
C9	0.29770 (17)	0.41677 (17)	0.10355 (12)	0.0686 (5)
H9A	0.2986	0.5096	0.1276	0.082*
H9B	0.3662	0.3652	0.1358	0.082*
C14	0.49535 (15)	0.23206 (17)	−0.02544 (13)	0.0645 (5)
H14A	0.5033	0.1983	0.0346	0.077*
C11	0.47090 (17)	0.3350 (2)	−0.20846 (13)	0.0726 (5)
H11A	0.4634	0.3686	−0.2685	0.087*
C16	0.0198 (2)	−0.30666 (19)	0.12294 (15)	0.0849 (6)
H16A	−0.0029	−0.4022	0.1210	0.127*
H16B	0.0680	−0.2874	0.1790	0.127*
H16C	0.0742	−0.2843	0.0706	0.127*
C13	0.56525 (17)	0.17720 (19)	−0.09722 (16)	0.0749 (5)
H13A	0.6227	0.1043	−0.0858	0.090*
C12	0.55298 (18)	0.2276 (2)	−0.18771 (15)	0.0789 (6)
H12A	0.6019	0.1869	−0.2348	0.095*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C6	0.0503 (8)	0.0535 (9)	0.0454 (8)	0.0052 (7)	0.0007 (6)	−0.0008 (6)
C1	0.0479 (8)	0.0541 (9)	0.0553 (9)	0.0068 (7)	0.0020 (7)	−0.0006 (7)
O1	0.0515 (7)	0.0615 (7)	0.1092 (10)	0.0037 (6)	0.0017 (6)	0.0002 (6)
N1	0.0569 (8)	0.0468 (7)	0.0714 (9)	−0.0024 (6)	0.0034 (7)	−0.0021 (6)
C7	0.0540 (9)	0.0546 (9)	0.0540 (9)	0.0036 (7)	0.0027 (7)	−0.0021 (7)
C2	0.0602 (10)	0.0557 (10)	0.0616 (10)	−0.0019 (8)	0.0038 (8)	−0.0002 (7)
O2	0.0719 (8)	0.0554 (8)	0.1357 (13)	−0.0061 (6)	0.0078 (7)	0.0005 (7)
C15	0.0457 (8)	0.0455 (8)	0.0713 (11)	−0.0068 (7)	0.0004 (7)	−0.0057 (8)
C5	0.0574 (9)	0.0560 (9)	0.0642 (11)	0.0106 (8)	−0.0008 (8)	−0.0021 (7)
C8	0.0709 (11)	0.0553 (10)	0.0673 (11)	−0.0026 (8)	0.0133 (8)	−0.0116 (8)
C10	0.0539 (9)	0.0505 (9)	0.0749 (12)	−0.0064 (7)	0.0018 (8)	0.0027 (8)
C3	0.0476 (9)	0.0776 (12)	0.0763 (12)	−0.0044 (8)	0.0004 (8)	−0.0033 (9)
C4	0.0490 (9)	0.0784 (12)	0.0753 (12)	0.0148 (9)	−0.0003 (8)	−0.0036 (9)
N2	0.0729 (10)	0.0502 (8)	0.0956 (12)	0.0069 (7)	0.0076 (9)	0.0091 (8)
N3	0.0787 (10)	0.0622 (9)	0.0869 (12)	0.0043 (8)	0.0062 (9)	0.0144 (8)
C9	0.0765 (11)	0.0552 (10)	0.0741 (12)	−0.0097 (8)	0.0007 (9)	−0.0131 (8)
C14	0.0487 (9)	0.0630 (10)	0.0818 (12)	0.0023 (8)	−0.0067 (8)	0.0019 (9)
C11	0.0723 (12)	0.0744 (12)	0.0713 (12)	−0.0151 (10)	0.0071 (9)	−0.0032 (9)
C16	0.0969 (15)	0.0560 (11)	0.1020 (16)	0.0096 (10)	0.0056 (12)	0.0026 (10)
C13	0.0529 (10)	0.0625 (11)	0.1093 (17)	0.0044 (8)	0.0037 (10)	−0.0078 (11)
C12	0.0686 (12)	0.0726 (13)	0.0957 (16)	−0.0102 (10)	0.0194 (10)	−0.0226 (11)

Geometric parameters (Å, º)

C6—C5	1.3864 (19)	C8—H8B	0.9700
C6—C1	1.396 (2)	C10—N3	1.380 (2)
C6—C7	1.490 (2)	C10—C11	1.397 (2)
C1—C2	1.376 (2)	C3—C4	1.368 (2)
C1—H1A	0.9300	C3—H3A	0.9300
O1—C7	1.2137 (17)	C4—H4A	0.9300
N1—N2	1.3518 (18)	N2—N3	1.304 (2)
N1—C15	1.3621 (19)	C9—H9A	0.9700
N1—C9	1.461 (2)	C9—H9B	0.9700
C7—C8	1.509 (2)	C14—C13	1.364 (3)
C2—O2	1.3618 (19)	C14—H14A	0.9300
C2—C3	1.389 (2)	C11—C12	1.366 (3)
O2—C16	1.415 (2)	C11—H11A	0.9300
C15—C10	1.382 (2)	C16—H16A	0.9600
C15—C14	1.389 (2)	C16—H16B	0.9600
C5—C4	1.381 (2)	C16—H16C	0.9600
C5—H5A	0.9300	C13—C12	1.401 (3)
C8—C9	1.516 (2)	C13—H13A	0.9300
C8—H8A	0.9700	C12—H12A	0.9300
C5—C6—C1	119.60 (14)	C4—C3—H3A	120.0
C5—C6—C7	122.41 (14)	C2—C3—H3A	120.0
C1—C6—C7	117.98 (13)	C3—C4—C5	120.75 (15)
C2—C1—C6	119.99 (14)	C3—C4—H4A	119.6
C2—C1—H1A	120.0	C5—C4—H4A	119.6
C6—C1—H1A	120.0	N3—N2—N1	109.23 (14)
N2—N1—C15	109.98 (14)	N2—N3—C10	107.59 (14)
N2—N1—C9	119.16 (14)	N1—C9—C8	112.15 (13)
C15—N1—C9	130.86 (14)	N1—C9—H9A	109.2
O1—C7—C6	121.11 (14)	C8—C9—H9A	109.2
O1—C7—C8	120.39 (15)	N1—C9—H9B	109.2
C6—C7—C8	118.50 (13)	C8—C9—H9B	109.2
O2—C2—C1	124.88 (15)	H9A—C9—H9B	107.9
O2—C2—C3	115.19 (14)	C13—C14—C15	116.38 (17)
C1—C2—C3	119.93 (16)	C13—C14—H14A	121.8
C2—O2—C16	118.52 (14)	C15—C14—H14A	121.8
N1—C15—C10	104.29 (14)	C12—C11—C10	117.16 (18)
N1—C15—C14	133.17 (16)	C12—C11—H11A	121.4
C10—C15—C14	122.54 (15)	C10—C11—H11A	121.4
C4—C5—C6	119.71 (15)	O2—C16—H16A	109.5
C4—C5—H5A	120.1	O2—C16—H16B	109.5
C6—C5—H5A	120.1	H16A—C16—H16B	109.5
C7—C8—C9	114.23 (14)	O2—C16—H16C	109.5
C7—C8—H8A	108.7	H16A—C16—H16C	109.5
C9—C8—H8A	108.7	H16B—C16—H16C	109.5
C7—C8—H8B	108.7	C14—C13—C12	121.86 (18)
C9—C8—H8B	108.7	C14—C13—H13A	119.1
H8A—C8—H8B	107.6	C12—C13—H13A	119.1
N3—C10—C15	108.91 (15)	C11—C12—C13	121.62 (17)
N3—C10—C11	130.65 (17)	C11—C12—H12A	119.2
C15—C10—C11	120.44 (16)	C13—C12—H12A	119.2
C4—C3—C2	120.01 (16)
C5—C6—C1—C2	1.0 (2)	C14—C15—C10—C11	0.0 (2)
C7—C6—C1—C2	−177.97 (13)	O2—C2—C3—C4	−179.68 (16)
C5—C6—C7—O1	−175.57 (15)	C1—C2—C3—C4	0.2 (3)
C1—C6—C7—O1	3.4 (2)	C2—C3—C4—C5	0.1 (3)
C5—C6—C7—C8	5.0 (2)	C6—C5—C4—C3	0.1 (3)
C1—C6—C7—C8	−176.05 (13)	C15—N1—N2—N3	0.17 (17)
C6—C1—C2—O2	179.11 (14)	C9—N1—N2—N3	179.87 (13)
C6—C1—C2—C3	−0.8 (2)	N1—N2—N3—C10	−0.01 (18)
C1—C2—O2—C16	4.0 (3)	C15—C10—N3—N2	−0.16 (18)
C3—C2—O2—C16	−176.08 (16)	C11—C10—N3—N2	179.94 (17)
N2—N1—C15—C10	−0.26 (16)	N2—N1—C9—C8	76.33 (18)
C9—N1—C15—C10	−179.91 (14)	C15—N1—C9—C8	−104.05 (18)
N2—N1—C15—C14	179.94 (16)	C7—C8—C9—N1	76.65 (19)
C9—N1—C15—C14	0.3 (3)	N1—C15—C14—C13	179.83 (15)
C1—C6—C5—C4	−0.6 (2)	C10—C15—C14—C13	0.1 (2)
C7—C6—C5—C4	178.28 (14)	N3—C10—C11—C12	−179.93 (17)
O1—C7—C8—C9	8.6 (2)	C15—C10—C11—C12	0.2 (2)
C6—C7—C8—C9	−171.95 (13)	C15—C14—C13—C12	−0.3 (2)
N1—C15—C10—N3	0.25 (16)	C10—C11—C12—C13	−0.4 (2)
C14—C15—C10—N3	−179.92 (14)	C14—C13—C12—C11	0.5 (3)
N1—C15—C10—C11	−179.83 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···Cg3^i	0.93	2.91	3.805	162
C9—H9B···Cg3^ii	0.97	2.98	3.663	128

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