Literature DB >> 21583575

2-(1H-Benzotriazol-1-yl)-1-(3-methyl-benzo-yl)ethyl benzoate.

Wu-Lan Zeng, Lian-Cai Du, Lei Zhang, Fang-Fang Jian.

Abstract

In the title mol-ecule, C(23)H(19)N(3)O(3), the dihedral angles between the mean plane of the benzotriazole ring system and the benzene and phenyl rings are 9.67 (9) and 86.08 (10)°, respectively. The dihedral angle between the benzene and phenyl rings is 85.89 (11)°. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds link mol-ecules into chains along [010].

Entities: Chemical Disease Gene

Year: 2009 PMID： 21583575 PMCID： PMC2977413 DOI： 10.1107/S1600536809026853

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the pharmacological activities of 1H-benzotriazoles and their derivatives, see: Chen & Wu (2005 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C23H19N3O3 M = 385.41 Monoclinic, a = 10.1095 (5) Å b = 9.3849 (4) Å c = 20.7091 (10) Å β = 99.061 (4)° V = 1940.29 (16) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 298 K 0.30 × 0.10 × 0.10 mm

Data collection

Siemens SMART CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.974, T max = 0.991 16102 measured reflections 3301 independent reflections 2071 reflections with I > 2σ(I) R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.044 wR(F 2) = 0.110 S = 1.00 3301 reflections 262 parameters H-atom parameters constrained Δρmax = 0.19 e Å−3 Δρmin = −0.22 e Å−3 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026853/lh2841sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026853/lh2841Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₃H₁₉N₃O₃	F(000) = 808
M_r = 385.41	D_x = 1.319 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3301 reflections
a = 10.1095 (5) Å	θ = 2.0–25.0°
b = 9.3849 (4) Å	µ = 0.09 mm⁻¹
c = 20.7091 (10) Å	T = 298 K
β = 99.061 (4)°	Block, colorless
V = 1940.29 (16) Å³	0.30 × 0.10 × 0.10 mm
Z = 4

Siemens SMART CCD diffractometer	3301 independent reflections
Radiation source: fine-focus sealed tube	2071 reflections with I > 2σ(I)
graphite	R_int = 0.051
φ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.974, T_max = 0.991	k = −11→11
16102 measured reflections	l = −23→24

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0483P)² + 0.2024P] where P = (F_o² + 2F_c²)/3
3301 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

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.

	x	y	z	U_iso*/U_eq
O1	0.09785 (14)	0.45987 (15)	0.21346 (7)	0.0543 (4)
O2	0.17138 (13)	0.14124 (15)	0.23494 (7)	0.0508 (4)
O3	0.18369 (12)	0.29378 (14)	0.31866 (6)	0.0444 (4)
C1	0.0844 (2)	0.2945 (3)	0.51412 (11)	0.0562 (6)
C2	0.1674 (3)	0.2855 (3)	0.57479 (12)	0.0757 (8)
H2B	0.1432	0.2312	0.6086	0.091*
C3	0.2831 (3)	0.3582 (4)	0.58230 (14)	0.0886 (10)
H3A	0.3400	0.3535	0.6222	0.106*
C4	0.3204 (3)	0.4402 (3)	0.53236 (16)	0.0884 (9)
H4A	0.4022	0.4876	0.5397	0.106*
C5	0.2409 (3)	0.4538 (3)	0.47244 (13)	0.0677 (7)
H5A	0.2654	0.5103	0.4394	0.081*
C6	0.1216 (2)	0.3781 (2)	0.46443 (10)	0.0464 (5)
C7	−0.0004 (2)	0.4194 (2)	0.34864 (9)	0.0518 (6)
H7A	0.0510	0.5066	0.3485	0.062*
H7B	−0.0943	0.4431	0.3358	0.062*
C8	0.04164 (19)	0.3168 (2)	0.29917 (9)	0.0431 (5)
H8A	−0.0068	0.2265	0.3000	0.052*
C9	0.0140 (2)	0.3818 (2)	0.23043 (9)	0.0402 (5)
C10	−0.11527 (19)	0.3540 (2)	0.18760 (9)	0.0391 (5)
C11	−0.2093 (2)	0.2566 (2)	0.20324 (11)	0.0521 (6)
H11A	−0.1922	0.2043	0.2418	0.062*
C12	−0.3285 (2)	0.2383 (3)	0.16091 (12)	0.0634 (7)
H12A	−0.3912	0.1729	0.1711	0.076*
C13	−0.3551 (2)	0.3158 (2)	0.10391 (11)	0.0586 (6)
H13A	−0.4359	0.3025	0.0762	0.070*
C14	−0.2632 (2)	0.4134 (2)	0.08716 (10)	0.0479 (5)
C15	−0.1438 (2)	0.4296 (2)	0.12935 (10)	0.0442 (5)
H15A	−0.0804	0.4932	0.1184	0.053*
C16	−0.2919 (3)	0.4998 (3)	0.02543 (11)	0.0743 (8)
H16A	−0.3786	0.4747	0.0022	0.112*
H16B	−0.2250	0.4804	−0.0015	0.112*
H16C	−0.2905	0.5993	0.0362	0.112*
C17	0.2376 (2)	0.1978 (2)	0.28153 (10)	0.0395 (5)
C18	0.38089 (19)	0.1709 (2)	0.30448 (9)	0.0412 (5)
C19	0.4567 (2)	0.2509 (2)	0.35264 (11)	0.0599 (7)
H19A	0.4178	0.3263	0.3720	0.072*
C20	0.5906 (2)	0.2187 (3)	0.37213 (12)	0.0713 (8)
H20A	0.6414	0.2733	0.4044	0.086*
C21	0.6490 (2)	0.1080 (3)	0.34462 (12)	0.0637 (7)
H21A	0.7390	0.0871	0.3581	0.076*
C22	0.5745 (2)	0.0282 (3)	0.29719 (12)	0.0604 (6)
H22A	0.6140	−0.0479	0.2787	0.072*
C23	0.4409 (2)	0.0590 (2)	0.27624 (11)	0.0514 (6)
H23A	0.3915	0.0049	0.2433	0.062*
N1	−0.0359 (2)	0.2318 (2)	0.49227 (10)	0.0793 (7)
N2	−0.07420 (19)	0.2723 (2)	0.43222 (10)	0.0730 (6)
N3	0.01911 (17)	0.36109 (19)	0.41419 (8)	0.0487 (5)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0460 (9)	0.0623 (10)	0.0531 (10)	−0.0116 (8)	0.0031 (7)	0.0094 (8)
O2	0.0483 (9)	0.0567 (9)	0.0447 (9)	−0.0043 (7)	−0.0009 (7)	−0.0106 (8)
O3	0.0398 (8)	0.0517 (9)	0.0394 (8)	0.0079 (7)	−0.0005 (6)	−0.0068 (7)
C1	0.0569 (15)	0.0742 (17)	0.0380 (14)	0.0125 (13)	0.0090 (12)	0.0009 (12)
C2	0.085 (2)	0.102 (2)	0.0395 (15)	0.0252 (18)	0.0090 (14)	0.0056 (14)
C3	0.078 (2)	0.136 (3)	0.0470 (18)	0.021 (2)	−0.0036 (16)	−0.0203 (18)
C4	0.0663 (18)	0.119 (3)	0.076 (2)	−0.0130 (17)	−0.0001 (17)	−0.040 (2)
C5	0.0687 (17)	0.0741 (17)	0.0603 (17)	−0.0128 (14)	0.0101 (14)	−0.0133 (14)
C6	0.0483 (13)	0.0536 (14)	0.0371 (13)	0.0106 (11)	0.0059 (11)	−0.0030 (11)
C7	0.0539 (14)	0.0633 (15)	0.0375 (13)	0.0198 (11)	0.0047 (11)	0.0069 (11)
C8	0.0360 (12)	0.0521 (13)	0.0397 (13)	0.0054 (10)	0.0008 (9)	0.0040 (10)
C9	0.0402 (12)	0.0422 (12)	0.0382 (12)	0.0050 (10)	0.0055 (10)	−0.0008 (10)
C10	0.0384 (12)	0.0415 (12)	0.0371 (12)	0.0015 (9)	0.0046 (9)	−0.0018 (10)
C11	0.0444 (13)	0.0583 (14)	0.0517 (14)	−0.0003 (11)	0.0021 (11)	0.0108 (11)
C12	0.0461 (14)	0.0701 (17)	0.0704 (18)	−0.0134 (12)	−0.0017 (12)	0.0155 (14)
C13	0.0472 (14)	0.0683 (16)	0.0547 (15)	−0.0041 (12)	−0.0090 (11)	−0.0019 (13)
C14	0.0500 (14)	0.0533 (14)	0.0389 (13)	0.0071 (11)	0.0021 (11)	−0.0007 (10)
C15	0.0403 (12)	0.0511 (14)	0.0405 (13)	−0.0014 (10)	0.0039 (10)	0.0014 (10)
C16	0.0744 (18)	0.092 (2)	0.0504 (15)	0.0029 (14)	−0.0092 (13)	0.0170 (14)
C17	0.0450 (13)	0.0398 (12)	0.0332 (12)	−0.0006 (10)	0.0045 (10)	0.0024 (10)
C18	0.0416 (12)	0.0432 (12)	0.0391 (12)	0.0001 (10)	0.0072 (10)	0.0032 (10)
C19	0.0476 (14)	0.0673 (16)	0.0611 (16)	0.0089 (12)	−0.0033 (12)	−0.0190 (13)
C20	0.0485 (15)	0.0864 (19)	0.0734 (18)	0.0059 (14)	−0.0077 (13)	−0.0231 (15)
C21	0.0421 (14)	0.0818 (18)	0.0669 (17)	0.0119 (13)	0.0079 (13)	0.0018 (15)
C22	0.0508 (15)	0.0639 (16)	0.0683 (17)	0.0132 (12)	0.0151 (13)	−0.0050 (13)
C23	0.0490 (14)	0.0518 (14)	0.0538 (14)	0.0006 (11)	0.0094 (11)	−0.0057 (11)
N1	0.0728 (15)	0.1137 (19)	0.0527 (14)	−0.0127 (14)	0.0142 (12)	0.0184 (13)
N2	0.0516 (12)	0.1129 (18)	0.0558 (14)	−0.0102 (12)	0.0118 (10)	0.0085 (13)
N3	0.0431 (11)	0.0660 (13)	0.0367 (11)	0.0073 (9)	0.0057 (9)	0.0051 (9)

O1—C9	1.213 (2)	C11—H11A	0.9300
O2—C17	1.207 (2)	C12—C13	1.377 (3)
O3—C17	1.353 (2)	C12—H12A	0.9300
O3—C8	1.445 (2)	C13—C14	1.387 (3)
C1—N1	1.363 (3)	C13—H13A	0.9300
C1—C6	1.392 (3)	C14—C15	1.382 (3)
C1—C2	1.399 (3)	C14—C16	1.503 (3)
C2—C3	1.342 (4)	C15—H15A	0.9300
C2—H2B	0.9300	C16—H16A	0.9600
C3—C4	1.388 (4)	C16—H16B	0.9600
C3—H3A	0.9300	C16—H16C	0.9600
C4—C5	1.374 (4)	C17—C18	1.474 (3)
C4—H4A	0.9300	C18—C19	1.380 (3)
C5—C6	1.387 (3)	C18—C23	1.387 (3)
C5—H5A	0.9300	C19—C20	1.384 (3)
C6—N3	1.357 (2)	C19—H19A	0.9300
C7—N3	1.448 (2)	C20—C21	1.363 (3)
C7—C8	1.515 (3)	C20—H20A	0.9300
C7—H7A	0.9700	C21—C22	1.364 (3)
C7—H7B	0.9700	C21—H21A	0.9300
C8—C9	1.534 (3)	C22—C23	1.382 (3)
C8—H8A	0.9800	C22—H22A	0.9300
C9—C10	1.482 (3)	C23—H23A	0.9300
C10—C15	1.390 (3)	N1—N2	1.300 (3)
C10—C11	1.393 (3)	N2—N3	1.355 (2)
C11—C12	1.385 (3)

?···?	?

C17—O3—C8	114.33 (15)	C11—C12—H12A	119.7
N1—C1—C6	109.2 (2)	C12—C13—C14	121.0 (2)
N1—C1—C2	130.5 (2)	C12—C13—H13A	119.5
C6—C1—C2	120.3 (2)	C14—C13—H13A	119.5
C3—C2—C1	117.5 (3)	C15—C14—C13	117.8 (2)
C3—C2—H2B	121.3	C15—C14—C16	120.7 (2)
C1—C2—H2B	121.3	C13—C14—C16	121.4 (2)
C2—C3—C4	122.0 (3)	C14—C15—C10	122.27 (19)
C2—C3—H3A	119.0	C14—C15—H15A	118.9
C4—C3—H3A	119.0	C10—C15—H15A	118.9
C5—C4—C3	122.4 (3)	C14—C16—H16A	109.5
C5—C4—H4A	118.8	C14—C16—H16B	109.5
C3—C4—H4A	118.8	H16A—C16—H16B	109.5
C4—C5—C6	115.8 (2)	C14—C16—H16C	109.5
C4—C5—H5A	122.1	H16A—C16—H16C	109.5
C6—C5—H5A	122.1	H16B—C16—H16C	109.5
N3—C6—C5	134.1 (2)	O2—C17—O3	121.65 (18)
N3—C6—C1	103.80 (19)	O2—C17—C18	125.15 (19)
C5—C6—C1	122.1 (2)	O3—C17—C18	113.20 (17)
N3—C7—C8	112.51 (16)	C19—C18—C23	119.12 (19)
N3—C7—H7A	109.1	C19—C18—C17	123.06 (19)
C8—C7—H7A	109.1	C23—C18—C17	117.82 (18)
N3—C7—H7B	109.1	C18—C19—C20	119.9 (2)
C8—C7—H7B	109.1	C18—C19—H19A	120.1
H7A—C7—H7B	107.8	C20—C19—H19A	120.1
O3—C8—C7	106.18 (16)	C21—C20—C19	120.8 (2)
O3—C8—C9	110.28 (15)	C21—C20—H20A	119.6
C7—C8—C9	110.21 (16)	C19—C20—H20A	119.6
O3—C8—H8A	110.0	C22—C21—C20	119.5 (2)
C7—C8—H8A	110.0	C22—C21—H21A	120.2
C9—C8—H8A	110.0	C20—C21—H21A	120.2
O1—C9—C10	121.57 (18)	C21—C22—C23	120.9 (2)
O1—C9—C8	118.38 (18)	C21—C22—H22A	119.6
C10—C9—C8	119.99 (18)	C23—C22—H22A	119.6
C15—C10—C11	118.72 (19)	C22—C23—C18	119.8 (2)
C15—C10—C9	118.17 (18)	C22—C23—H23A	120.1
C11—C10—C9	123.11 (18)	C18—C23—H23A	120.1
C12—C11—C10	119.5 (2)	N2—N1—C1	107.9 (2)
C12—C11—H11A	120.3	N1—N2—N3	109.15 (19)
C10—C11—H11A	120.3	C6—N3—N2	109.98 (17)
C13—C12—C11	120.7 (2)	C6—N3—C7	130.49 (19)
C13—C12—H12A	119.7	N2—N3—C7	119.52 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O2ⁱ	0.97	2.42	3.062 (2)	123
C11—H11A···O1ⁱⁱ	0.93	2.60	3.375 (2)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯O2ⁱ	0.97	2.42	3.062 (2)	123
C11—H11A⋯O1ⁱⁱ	0.93	2.60	3.375 (2)	141

Symmetry codes: (i) ; (ii) .

3 in total

2-(1H-Benzotriazol-1-yl)-1-(3-methyl-benzo-yl)ethyl benzoate.

Related literature

Experimental

Crystal data

Data collection

Refinement

1. A short history of SHELX.

2. Reaction of (Z)-1-aryl-3-hexen-1,5-diynes with sodium azide: synthesis of 1-aryl-1H-benzotriazoles.

3. Structure validation in chemical crystallography.