2-(2H-Benzotriazol-2-yl)-1-phenyl­ethanone

The molecule of the title compound, C₁₄H₁₁N₃O, is non-planar, with a dihedral angle of 72.06 (9)° between the benzene and benzotriazole planes. Mol­ecules are linked into two-dimensional layers via weak C—H...N and C—H...O inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.042
• wR factor = 0.097
• Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.04
           From the CIF: _reflns_number_total               1477
           Count of symmetry unique reflns         1477
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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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: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

2-(2H-Benzotriazol-2-yl)-1-phenylethanone

Crystal data

C14H11N3O	Dx = 1.324 Mg m^−3
Mr = 237.26	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43212	Cell parameters from 2708 reflections
a = 8.1925 (3) Å	θ = 2.5–20.7°
c = 35.462 (3) Å	µ = 0.09 mm^−1
V = 2380.1 (2) Å^3	T = 293 K
Z = 8	Block, colorless
F(000) = 992	0.35 × 0.11 × 0.08 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	1477 independent reflections
Radiation source: fine-focus sealed tube	1277 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 8.33 pixels mm^-1	θmax = 26.0°, θmin = 2.3°
ω scans	h = −10→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→10
Tmin = 0.970, Tmax = 0.993	l = −43→30
14062 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) = 0.098	H-atom parameters constrained
S = 1.20	w = 1/[σ^2(Fo^2) + (0.0436P)^2 + 0.1331P] where P = (Fo^2 + 2Fc^2)/3
1477 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.12 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
O1	0.6220 (2)	0.3125 (2)	0.18567 (5)	0.0790 (6)
N1	0.9236 (2)	0.4583 (3)	0.13742 (5)	0.0580 (5)
N2	0.8248 (2)	0.3416 (2)	0.12580 (5)	0.0499 (5)
N3	0.7341 (2)	0.3708 (2)	0.09566 (5)	0.0537 (5)
C1	0.7796 (3)	−0.0940 (3)	0.19595 (6)	0.0648 (7)
H1B	0.8278	−0.1051	0.1723	0.078*
C2	0.7812 (4)	−0.2244 (4)	0.22049 (7)	0.0779 (8)
H2A	0.8276	−0.3230	0.2132	0.093*
C3	0.7143 (3)	−0.2085 (4)	0.25572 (7)	0.0702 (7)
H3B	0.7173	−0.2954	0.2726	0.084*
C4	0.6428 (3)	−0.0631 (4)	0.26602 (7)	0.0672 (7)
H4A	0.5975	−0.0520	0.2899	0.081*
C5	0.6379 (3)	0.0656 (3)	0.24126 (6)	0.0577 (6)
H5A	0.5872	0.1625	0.2483	0.069*
C6	0.7082 (3)	0.0523 (3)	0.20563 (6)	0.0480 (5)
C7	0.7053 (3)	0.1952 (3)	0.18001 (6)	0.0521 (5)
C8	0.8161 (3)	0.1872 (3)	0.14561 (6)	0.0568 (6)
H8A	0.9250	0.1557	0.1535	0.068*
H8B	0.7759	0.1039	0.1285	0.068*
C9	0.8969 (3)	0.5781 (3)	0.11209 (6)	0.0520 (6)
C10	0.9659 (4)	0.7347 (4)	0.10883 (8)	0.0756 (8)
H10A	1.0432	0.7723	0.1259	0.091*
C11	0.9146 (5)	0.8285 (4)	0.07957 (9)	0.0900 (10)
H11A	0.9583	0.9325	0.0766	0.108*
C12	0.7974 (5)	0.7727 (4)	0.05374 (8)	0.0869 (10)
H12A	0.7657	0.8417	0.0342	0.104*
C13	0.7285 (4)	0.6226 (4)	0.05602 (7)	0.0720 (8)
H13A	0.6517	0.5870	0.0385	0.086*
C14	0.7792 (3)	0.5235 (3)	0.08620 (6)	0.0499 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0829 (13)	0.0707 (12)	0.0834 (12)	0.0308 (11)	0.0214 (11)	0.0165 (11)
N1	0.0552 (12)	0.0641 (13)	0.0547 (11)	−0.0037 (11)	−0.0064 (10)	−0.0023 (10)
N2	0.0487 (11)	0.0538 (11)	0.0473 (10)	0.0007 (9)	−0.0002 (9)	0.0033 (9)
N3	0.0543 (12)	0.0610 (13)	0.0459 (10)	−0.0012 (10)	−0.0050 (9)	0.0051 (9)
C1	0.0793 (18)	0.0652 (16)	0.0499 (13)	0.0152 (14)	0.0084 (13)	0.0087 (12)
C2	0.096 (2)	0.0660 (17)	0.0713 (17)	0.0203 (17)	0.0054 (16)	0.0143 (14)
C3	0.0762 (18)	0.0739 (18)	0.0604 (15)	−0.0043 (15)	−0.0050 (14)	0.0201 (14)
C4	0.0689 (18)	0.083 (2)	0.0497 (13)	−0.0158 (15)	0.0050 (12)	0.0046 (14)
C5	0.0509 (14)	0.0630 (15)	0.0592 (14)	−0.0015 (12)	0.0077 (12)	−0.0028 (12)
C6	0.0415 (12)	0.0557 (14)	0.0468 (12)	−0.0010 (11)	−0.0048 (10)	0.0027 (10)
C7	0.0456 (12)	0.0565 (14)	0.0541 (13)	0.0064 (12)	−0.0020 (11)	0.0019 (11)
C8	0.0609 (15)	0.0538 (14)	0.0556 (13)	0.0083 (12)	0.0033 (12)	0.0091 (11)
C9	0.0532 (14)	0.0536 (14)	0.0493 (12)	−0.0010 (11)	0.0117 (11)	−0.0045 (11)
C10	0.084 (2)	0.0646 (18)	0.0782 (18)	−0.0166 (16)	0.0203 (16)	−0.0135 (16)
C11	0.129 (3)	0.0518 (17)	0.089 (2)	−0.0094 (18)	0.052 (2)	−0.0011 (16)
C12	0.132 (3)	0.0641 (19)	0.0648 (17)	0.022 (2)	0.0315 (19)	0.0175 (15)
C13	0.089 (2)	0.0753 (19)	0.0514 (14)	0.0128 (17)	0.0051 (14)	0.0108 (14)
C14	0.0529 (14)	0.0553 (14)	0.0416 (12)	0.0019 (11)	0.0077 (11)	0.0026 (10)

Geometric parameters (Å, º)

O1—C7	1.196 (3)	C5—H5A	0.9300
N1—N2	1.319 (2)	C6—C7	1.482 (3)
N1—C9	1.348 (3)	C7—C8	1.522 (3)
N2—N3	1.323 (2)	C8—H8A	0.9700
N2—C8	1.449 (3)	C8—H8B	0.9700
N3—C14	1.347 (3)	C9—C14	1.405 (3)
C1—C6	1.377 (3)	C9—C10	1.406 (4)
C1—C2	1.378 (3)	C10—C11	1.358 (4)
C1—H1B	0.9300	C10—H10A	0.9300
C2—C3	1.370 (3)	C11—C12	1.404 (4)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.377 (4)	C12—C13	1.356 (4)
C3—H3B	0.9300	C12—H12A	0.9300
C4—C5	1.373 (3)	C13—C14	1.406 (3)
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.393 (3)
N2—N1—C9	102.73 (17)	C6—C7—C8	116.6 (2)
N1—N2—N3	117.78 (19)	N2—C8—C7	112.33 (19)
N1—N2—C8	120.78 (19)	N2—C8—H8A	109.1
N3—N2—C8	121.4 (2)	C7—C8—H8A	109.1
N2—N3—C14	102.42 (18)	N2—C8—H8B	109.1
C6—C1—C2	121.4 (2)	C7—C8—H8B	109.1
C6—C1—H1B	119.3	H8A—C8—H8B	107.9
C2—C1—H1B	119.3	N1—C9—C14	108.3 (2)
C3—C2—C1	119.9 (3)	N1—C9—C10	130.8 (2)
C3—C2—H2A	120.0	C14—C9—C10	120.8 (2)
C1—C2—H2A	120.0	C11—C10—C9	117.1 (3)
C2—C3—C4	119.6 (2)	C11—C10—H10A	121.5
C2—C3—H3B	120.2	C9—C10—H10A	121.5
C4—C3—H3B	120.2	C10—C11—C12	121.8 (3)
C5—C4—C3	120.5 (2)	C10—C11—H11A	119.1
C5—C4—H4A	119.8	C12—C11—H11A	119.1
C3—C4—H4A	119.8	C13—C12—C11	122.8 (3)
C4—C5—C6	120.5 (2)	C13—C12—H12A	118.6
C4—C5—H5A	119.7	C11—C12—H12A	118.6
C6—C5—H5A	119.7	C12—C13—C14	116.5 (3)
C1—C6—C5	118.0 (2)	C12—C13—H13A	121.8
C1—C6—C7	122.8 (2)	C14—C13—H13A	121.8
C5—C6—C7	119.2 (2)	N3—C14—C9	108.73 (19)
O1—C7—C6	122.8 (2)	N3—C14—C13	130.2 (2)
O1—C7—C8	120.6 (2)	C9—C14—C13	121.1 (2)
C9—N1—N2—N3	−0.5 (2)	O1—C7—C8—N2	8.8 (3)
C9—N1—N2—C8	179.68 (19)	C6—C7—C8—N2	−170.60 (19)
N1—N2—N3—C14	0.5 (2)	N2—N1—C9—C14	0.3 (2)
C8—N2—N3—C14	−179.7 (2)	N2—N1—C9—C10	−179.6 (2)
C6—C1—C2—C3	−1.6 (5)	N1—C9—C10—C11	179.3 (3)
C1—C2—C3—C4	1.4 (5)	C14—C9—C10—C11	−0.5 (4)
C2—C3—C4—C5	0.1 (4)	C9—C10—C11—C12	0.3 (4)
C3—C4—C5—C6	−1.4 (4)	C10—C11—C12—C13	−0.3 (5)
C2—C1—C6—C5	0.4 (4)	C11—C12—C13—C14	0.6 (4)
C2—C1—C6—C7	179.6 (2)	N2—N3—C14—C9	−0.2 (2)
C4—C5—C6—C1	1.1 (4)	N2—N3—C14—C13	178.7 (2)
C4—C5—C6—C7	−178.2 (2)	N1—C9—C14—N3	0.0 (3)
C1—C6—C7—O1	167.7 (3)	C10—C9—C14—N3	179.9 (2)
C5—C6—C7—O1	−13.0 (4)	N1—C9—C14—C13	−179.0 (2)
C1—C6—C7—C8	−12.8 (3)	C10—C9—C14—C13	0.9 (3)
C5—C6—C7—C8	166.4 (2)	C12—C13—C14—N3	−179.6 (2)
N1—N2—C8—C7	82.1 (3)	C12—C13—C14—C9	−0.8 (4)
N3—N2—C8—C7	−97.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···N3^i	0.97	2.54	3.471 (3)	160
C11—H11A···O1^ii	0.93	2.52	3.439 (3)	170

Symmetry codes: (i) x+1/2, −y+1/2, −z+1/4; (ii) x+1/2, −y+3/2, −z+1/4.