2-(1H-1,2,3-Benzotriazol-1-ylmeth­yl)-1-(4-methyl­benzo­yl)ethyl benzoate

In the title compound, C₂₃H₁₉N₃O₂, the mol­ecules are linked into centrosymmetric dimers by C—H...O hydrogen bonds. The packing is further stabilized by C—H...π and π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.120
• Data-to-parameter ratio = 10.7

checkCIF/PLATON results

No syntax errors found



Alert level B
THETM01_ALERT_3_B  The value of sine(theta_max)/wavelength is less than 0.575
            Calculated sin(theta_max)/wavelength =    0.5559
PLAT023_ALERT_3_B Resolution (too) Low [sin(th)/Lambda < 0.6].....      23.27 Deg.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C23

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   2 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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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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, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

2-(1H-1,2,3-Benzotriazol-1-ylmethyl)-1-(4-methylbenzoyl)ethyl benzoate

Crystal data

C23H19N3O3	Z = 2
Mr = 385.41	F(000) = 404
Triclinic, P1	Dx = 1.312 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5987 (9) Å	Cell parameters from 2192 reflections
b = 10.2272 (9) Å	θ = 2.2–23.3°
c = 11.4321 (10) Å	µ = 0.09 mm^−1
α = 116.482 (1)°	T = 293 K
β = 96.928 (1)°	Block, colourless
γ = 97.444 (1)°	0.41 × 0.25 × 0.18 mm
V = 975.72 (15) Å^3

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	2808 independent reflections
Radiation source: fine-focus sealed tube	2400 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.011
Detector resolution: 8.33 pixels mm^-1	θmax = 23.3°, θmin = 2.0°
ω scans	h = −7→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→11
Tmin = 0.965, Tmax = 0.984	l = −12→12
4423 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0637P)^2 + 0.235P] where P = (Fo^2 + 2Fc^2)/3
2808 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.18 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	0.35691 (15)	−0.19998 (15)	−0.10902 (13)	0.0602 (4)
O2	0.27471 (13)	0.05300 (13)	0.02400 (12)	0.0487 (3)
O3	0.08513 (15)	−0.11326 (16)	0.00589 (14)	0.0624 (4)
N1	0.29377 (16)	0.23075 (16)	−0.12395 (14)	0.0463 (4)
N2	0.1929 (2)	0.2293 (2)	−0.21863 (17)	0.0636 (5)
N3	0.1584 (2)	0.3603 (2)	−0.17273 (19)	0.0715 (5)
C1	0.2678 (2)	−0.4053 (2)	−0.3791 (2)	0.0607 (6)
H1A	0.3230	−0.4327	−0.3245	0.073*
C2	0.2219 (2)	−0.5040 (2)	−0.5132 (2)	0.0687 (6)
H2A	0.2468	−0.5971	−0.5473	0.082*
C3	0.1398 (2)	−0.4676 (2)	−0.59828 (19)	0.0553 (5)
C4	0.1037 (2)	−0.3298 (2)	−0.5439 (2)	0.0617 (6)
H4A	0.0478	−0.3030	−0.5986	0.074*
C5	0.1487 (2)	−0.2300 (2)	−0.40962 (19)	0.0551 (5)
H5A	0.1225	−0.1377	−0.3756	0.066*
C6	0.23259 (19)	−0.26602 (19)	−0.32503 (17)	0.0429 (4)
C7	0.28356 (19)	−0.1651 (2)	−0.18038 (18)	0.0434 (4)
C8	0.2472 (2)	−0.00956 (19)	−0.11868 (16)	0.0434 (4)
H8A	0.1466	−0.0155	−0.1527	0.052*
C9	0.3454 (2)	0.0956 (2)	−0.14894 (18)	0.0467 (5)
H9A	0.4403	0.1220	−0.0944	0.056*
H9B	0.3536	0.0444	−0.2417	0.056*
C10	0.32478 (19)	0.36633 (19)	−0.01334 (18)	0.0431 (4)
C11	0.2376 (2)	0.4487 (2)	−0.0452 (2)	0.0539 (5)
C12	0.2421 (3)	0.5976 (2)	0.0466 (3)	0.0700 (6)
H12A	0.1842	0.6542	0.0269	0.084*
C13	0.3346 (3)	0.6554 (2)	0.1656 (3)	0.0731 (7)
H13A	0.3399	0.7537	0.2287	0.088*
C14	0.4221 (3)	0.5706 (2)	0.1955 (2)	0.0679 (6)
H14A	0.4842	0.6147	0.2781	0.081*
C15	0.4197 (2)	0.4258 (2)	0.10813 (19)	0.0537 (5)
H15A	0.4782	0.3701	0.1287	0.064*
C16	0.1889 (2)	−0.0166 (2)	0.07369 (19)	0.0452 (5)
C17	0.2401 (2)	0.03695 (19)	0.21784 (18)	0.0449 (4)
C18	0.3727 (2)	0.1293 (2)	0.28646 (19)	0.0563 (5)
H18A	0.4305	0.1655	0.2433	0.068*
C19	0.4191 (3)	0.1678 (3)	0.4183 (2)	0.0728 (7)
H19A	0.5094	0.2278	0.4635	0.087*
C20	0.3328 (3)	0.1180 (3)	0.4833 (2)	0.0782 (7)
H20A	0.3645	0.1446	0.5727	0.094*
C21	0.2002 (3)	0.0293 (3)	0.4175 (2)	0.0731 (7)
H21A	0.1412	−0.0023	0.4628	0.088*
C22	0.1535 (2)	−0.0135 (2)	0.2842 (2)	0.0597 (5)
H22A	0.0644	−0.0759	0.2391	0.072*
C23	0.0879 (3)	−0.5780 (3)	−0.7435 (2)	0.0754 (7)
H23A	0.0330	−0.5343	−0.7871	0.113*
H23B	0.0288	−0.6661	−0.7518	0.113*
H23C	0.1687	−0.6040	−0.7844	0.113*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0681 (9)	0.0606 (9)	0.0491 (8)	0.0238 (7)	−0.0002 (7)	0.0236 (7)
O2	0.0560 (8)	0.0449 (7)	0.0397 (7)	0.0043 (6)	0.0080 (6)	0.0170 (6)
O3	0.0560 (9)	0.0594 (9)	0.0623 (9)	−0.0034 (7)	−0.0002 (7)	0.0271 (8)
N1	0.0539 (9)	0.0443 (9)	0.0409 (9)	0.0093 (7)	0.0033 (7)	0.0220 (8)
N2	0.0714 (12)	0.0669 (12)	0.0517 (10)	0.0116 (9)	−0.0038 (9)	0.0317 (9)
N3	0.0808 (13)	0.0714 (13)	0.0717 (13)	0.0232 (10)	−0.0006 (11)	0.0436 (11)
C1	0.0653 (13)	0.0495 (12)	0.0566 (13)	0.0183 (10)	−0.0005 (10)	0.0171 (10)
C2	0.0740 (15)	0.0473 (12)	0.0615 (14)	0.0181 (11)	0.0052 (12)	0.0062 (11)
C3	0.0539 (12)	0.0523 (12)	0.0439 (11)	−0.0029 (9)	0.0079 (9)	0.0130 (9)
C4	0.0740 (14)	0.0578 (13)	0.0457 (12)	0.0060 (11)	−0.0036 (10)	0.0234 (11)
C5	0.0696 (13)	0.0435 (11)	0.0470 (11)	0.0131 (10)	0.0031 (10)	0.0184 (9)
C6	0.0438 (10)	0.0393 (10)	0.0418 (10)	0.0074 (8)	0.0056 (8)	0.0169 (8)
C7	0.0424 (10)	0.0442 (10)	0.0430 (10)	0.0078 (8)	0.0047 (8)	0.0211 (9)
C8	0.0479 (10)	0.0417 (10)	0.0358 (9)	0.0091 (8)	0.0041 (8)	0.0151 (8)
C9	0.0537 (11)	0.0418 (10)	0.0411 (10)	0.0107 (8)	0.0098 (8)	0.0163 (8)
C10	0.0461 (10)	0.0394 (10)	0.0447 (10)	0.0086 (8)	0.0097 (8)	0.0205 (9)
C11	0.0595 (12)	0.0511 (12)	0.0603 (13)	0.0152 (10)	0.0115 (10)	0.0332 (11)
C12	0.0789 (16)	0.0545 (14)	0.0932 (18)	0.0288 (12)	0.0264 (14)	0.0428 (14)
C13	0.0885 (17)	0.0411 (12)	0.0804 (17)	0.0159 (12)	0.0274 (14)	0.0173 (12)
C14	0.0739 (15)	0.0512 (13)	0.0571 (13)	0.0064 (11)	0.0044 (11)	0.0109 (11)
C15	0.0557 (12)	0.0470 (12)	0.0515 (12)	0.0120 (9)	0.0050 (10)	0.0182 (10)
C16	0.0458 (11)	0.0390 (10)	0.0504 (11)	0.0117 (9)	0.0102 (9)	0.0197 (9)
C17	0.0505 (11)	0.0412 (10)	0.0439 (10)	0.0147 (8)	0.0131 (9)	0.0185 (9)
C18	0.0593 (13)	0.0593 (13)	0.0447 (11)	0.0044 (10)	0.0136 (10)	0.0209 (10)
C19	0.0740 (15)	0.0805 (16)	0.0460 (12)	−0.0024 (12)	0.0043 (11)	0.0209 (12)
C20	0.102 (2)	0.0799 (17)	0.0468 (13)	0.0044 (15)	0.0107 (13)	0.0290 (12)
C21	0.0920 (18)	0.0763 (16)	0.0619 (14)	0.0110 (14)	0.0299 (13)	0.0399 (13)
C22	0.0580 (13)	0.0608 (13)	0.0657 (14)	0.0106 (10)	0.0174 (11)	0.0336 (11)
C23	0.0763 (16)	0.0711 (16)	0.0478 (12)	−0.0070 (12)	0.0084 (11)	0.0079 (11)

Geometric parameters (Å, º)

O1—C7	1.214 (2)	C10—C15	1.388 (3)
O2—C16	1.352 (2)	C10—C11	1.388 (3)
O2—C8	1.436 (2)	C11—C12	1.403 (3)
O3—C16	1.202 (2)	C12—C13	1.357 (3)
N1—N2	1.356 (2)	C12—H12A	0.9300
N1—C10	1.360 (2)	C13—C14	1.399 (3)
N1—C9	1.448 (2)	C13—H13A	0.9300
N2—N3	1.308 (2)	C14—C15	1.363 (3)
N3—C11	1.378 (3)	C14—H14A	0.9300
C1—C2	1.380 (3)	C15—H15A	0.9300
C1—C6	1.384 (3)	C16—C17	1.479 (3)
C1—H1A	0.9300	C17—C18	1.384 (3)
C2—C3	1.386 (3)	C17—C22	1.387 (3)
C2—H2A	0.9300	C18—C19	1.375 (3)
C3—C4	1.374 (3)	C18—H18A	0.9300
C3—C23	1.504 (3)	C19—C20	1.370 (3)
C4—C5	1.383 (3)	C19—H19A	0.9300
C4—H4A	0.9300	C20—C21	1.368 (3)
C5—C6	1.387 (3)	C20—H20A	0.9300
C5—H5A	0.9300	C21—C22	1.380 (3)
C6—C7	1.480 (2)	C21—H21A	0.9300
C7—C8	1.534 (2)	C22—H22A	0.9300
C8—C9	1.521 (2)	C23—H23A	0.9600
C8—H8A	0.9800	C23—H23B	0.9600
C9—H9A	0.9700	C23—H23C	0.9600
C9—H9B	0.9700
C16—O2—C8	115.83 (14)	N3—C11—C10	108.63 (17)
N2—N1—C10	110.27 (15)	N3—C11—C12	131.0 (2)
N2—N1—C9	119.28 (15)	C10—C11—C12	120.4 (2)
C10—N1—C9	130.37 (15)	C13—C12—C11	117.1 (2)
N3—N2—N1	108.72 (16)	C13—C12—H12A	121.4
N2—N3—C11	108.05 (16)	C11—C12—H12A	121.4
C2—C1—C6	120.81 (19)	C12—C13—C14	121.6 (2)
C2—C1—H1A	119.6	C12—C13—H13A	119.2
C6—C1—H1A	119.6	C14—C13—H13A	119.2
C1—C2—C3	121.5 (2)	C15—C14—C13	122.4 (2)
C1—C2—H2A	119.3	C15—C14—H14A	118.8
C3—C2—H2A	119.3	C13—C14—H14A	118.8
C4—C3—C2	117.51 (18)	C14—C15—C10	116.07 (19)
C4—C3—C23	121.7 (2)	C14—C15—H15A	122.0
C2—C3—C23	120.7 (2)	C10—C15—H15A	122.0
C3—C4—C5	121.55 (19)	O3—C16—O2	122.85 (17)
C3—C4—H4A	119.2	O3—C16—C17	124.81 (17)
C5—C4—H4A	119.2	O2—C16—C17	112.32 (16)
C4—C5—C6	120.81 (19)	C18—C17—C22	119.34 (18)
C4—C5—H5A	119.6	C18—C17—C16	122.51 (17)
C6—C5—H5A	119.6	C22—C17—C16	118.09 (18)
C1—C6—C5	117.82 (17)	C19—C18—C17	120.18 (19)
C1—C6—C7	118.54 (16)	C19—C18—H18A	119.9
C5—C6—C7	123.62 (17)	C17—C18—H18A	119.9
O1—C7—C6	122.00 (17)	C20—C19—C18	120.1 (2)
O1—C7—C8	118.59 (16)	C20—C19—H19A	119.9
C6—C7—C8	119.38 (15)	C18—C19—H19A	119.9
O2—C8—C9	105.95 (14)	C21—C20—C19	120.3 (2)
O2—C8—C7	109.59 (14)	C21—C20—H20A	119.8
C9—C8—C7	110.18 (14)	C19—C20—H20A	119.8
O2—C8—H8A	110.3	C20—C21—C22	120.3 (2)
C9—C8—H8A	110.3	C20—C21—H21A	119.9
C7—C8—H8A	110.3	C22—C21—H21A	119.9
N1—C9—C8	112.55 (15)	C21—C22—C17	119.8 (2)
N1—C9—H9A	109.1	C21—C22—H22A	120.1
C8—C9—H9A	109.1	C17—C22—H22A	120.1
N1—C9—H9B	109.1	C3—C23—H23A	109.5
C8—C9—H9B	109.1	C3—C23—H23B	109.5
H9A—C9—H9B	107.8	H23A—C23—H23B	109.5
N1—C10—C15	133.26 (17)	C3—C23—H23C	109.5
N1—C10—C11	104.33 (16)	H23A—C23—H23C	109.5
C15—C10—C11	122.40 (18)	H23B—C23—H23C	109.5
C10—N1—N2—N3	0.3 (2)	N2—N1—C10—C11	−0.1 (2)
C9—N1—N2—N3	177.37 (16)	C9—N1—C10—C11	−176.75 (17)
N1—N2—N3—C11	−0.4 (2)	N2—N3—C11—C10	0.3 (2)
C6—C1—C2—C3	0.2 (4)	N2—N3—C11—C12	179.4 (2)
C1—C2—C3—C4	−0.8 (3)	N1—C10—C11—N3	−0.1 (2)
C1—C2—C3—C23	−178.6 (2)	C15—C10—C11—N3	178.79 (18)
C2—C3—C4—C5	0.7 (3)	N1—C10—C11—C12	−179.29 (18)
C23—C3—C4—C5	178.4 (2)	C15—C10—C11—C12	−0.4 (3)
C3—C4—C5—C6	0.1 (3)	N3—C11—C12—C13	−178.8 (2)
C2—C1—C6—C5	0.7 (3)	C10—C11—C12—C13	0.2 (3)
C2—C1—C6—C7	179.48 (19)	C11—C12—C13—C14	0.2 (3)
C4—C5—C6—C1	−0.8 (3)	C12—C13—C14—C15	−0.2 (4)
C4—C5—C6—C7	−179.57 (18)	C13—C14—C15—C10	0.0 (3)
C1—C6—C7—O1	1.3 (3)	N1—C10—C15—C14	178.84 (19)
C5—C6—C7—O1	−179.98 (19)	C11—C10—C15—C14	0.3 (3)
C1—C6—C7—C8	179.31 (17)	C8—O2—C16—O3	−8.7 (2)
C5—C6—C7—C8	−2.0 (3)	C8—O2—C16—C17	169.76 (13)
C16—O2—C8—C9	174.41 (14)	O3—C16—C17—C18	168.57 (19)
C16—O2—C8—C7	−66.74 (18)	O2—C16—C17—C18	−9.8 (2)
O1—C7—C8—O2	−16.3 (2)	O3—C16—C17—C22	−8.5 (3)
C6—C7—C8—O2	165.61 (15)	O2—C16—C17—C22	173.10 (16)
O1—C7—C8—C9	99.91 (19)	C22—C17—C18—C19	1.4 (3)
C6—C7—C8—C9	−78.2 (2)	C16—C17—C18—C19	−175.62 (19)
N2—N1—C9—C8	−83.0 (2)	C17—C18—C19—C20	−1.7 (4)
C10—N1—C9—C8	93.4 (2)	C18—C19—C20—C21	0.3 (4)
O2—C8—C9—N1	−76.41 (17)	C19—C20—C21—C22	1.4 (4)
C7—C8—C9—N1	165.12 (14)	C20—C21—C22—C17	−1.7 (4)
N2—N1—C10—C15	−178.8 (2)	C18—C17—C22—C21	0.2 (3)
C9—N1—C10—C15	4.6 (3)	C16—C17—C22—C21	177.43 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23C···Cg^i	0.96	2.85	3.572	133
C9—H9A···O1^ii	0.97	2.59	3.517 (2)	161
C15—H15A···O1^ii	0.93	2.46	3.351 (3)	161

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