Literature DB >> 21577573

2-(1H-Benzotriazol-1-yl)-1-(4-ethyl-benzo-yl)ethyl 2-chloro-benzoate.

Abstract

In the crystal structure of the title compound, C(24)H(20)ClN(3)O(3), weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into chains extended along the a axis. The crystal studied was found to be an inversion twin.

Entities: Chemical Disease Gene

Year: 2009 PMID： 21577573 PMCID： PMC2969880 DOI： 10.1107/S1600536809031912

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

Related literature

For background to the pharmacological activity of 1H-benzotriazole and its derivative, see Chen & Wu (2005 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C24H20ClN3O3 M = 433.88 Orthorhombic, a = 9.433 (2) Å b = 14.824 (4) Å c = 15.239 (4) Å V = 2131.0 (10) Å3 Z = 4 Mo Kα radiation μ = 0.21 mm−1 T = 293 K 0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer Absorption correction: none 13991 measured reflections 5212 independent reflections 2174 reflections with I > 2σ(I) R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.057 wR(F 2) = 0.158 S = 0.91 5212 reflections 281 parameters H-atom parameters constrained Δρmax = 0.22 e Å−3 Δρmin = −0.20 e Å−3 Absolute structure: Flack (1983 ▶), 2244 Friedel pairs Flack parameter: 0.57 (12) Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031912/hb5022sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031912/hb5022Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₄H₂₀ClN₃O₃	F(000) = 904
M_r = 433.88	D_x = 1.352 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5212 reflections
a = 9.433 (2) Å	θ = 1.9–28.3°
b = 14.824 (4) Å	µ = 0.21 mm⁻¹
c = 15.239 (4) Å	T = 293 K
V = 2131.0 (10) Å³	Block, colourless
Z = 4	0.15 × 0.12 × 0.10 mm

Bruker SMART CCD diffractometer	2174 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.078
graphite	θ_max = 28.3°, θ_min = 1.9°
ω scans	h = −12→12
13991 measured reflections	k = −19→17
5212 independent reflections	l = −20→13

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.057	w = 1/[σ²(F_o²) + (0.0626P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.158	(Δ/σ)_max < 0.001
S = 0.91	Δρ_max = 0.22 e Å⁻³
5212 reflections	Δρ_min = −0.20 e Å⁻³
281 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0034 (10)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2214 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.57 (12)

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
Cl1	0.15025 (14)	0.62148 (8)	0.24883 (9)	0.0933 (5)
O1	−0.1687 (2)	0.61438 (14)	0.03013 (16)	0.0470 (6)
O2	−0.3655 (3)	0.73734 (15)	0.08575 (17)	0.0573 (7)
O3	−0.0410 (3)	0.69848 (17)	0.12131 (18)	0.0572 (7)
N1	−0.2042 (3)	0.6104 (2)	−0.15765 (19)	0.0497 (8)
N2	−0.1122 (4)	0.6446 (2)	−0.2173 (2)	0.0660 (10)
N3	−0.0555 (4)	0.5770 (3)	−0.2603 (2)	0.0788 (11)
C1	−0.1124 (5)	0.4984 (3)	−0.2287 (3)	0.0627 (12)
C2	−0.0891 (5)	0.4096 (3)	−0.2526 (3)	0.0803 (14)
H2B	−0.0234	0.3952	−0.2958	0.096*
C3	−0.1639 (7)	0.3446 (3)	−0.2116 (3)	0.0887 (17)
H3B	−0.1497	0.2846	−0.2270	0.106*
C4	−0.2615 (6)	0.3655 (3)	−0.1468 (3)	0.0806 (14)
H4A	−0.3124	0.3190	−0.1206	0.097*
C5	−0.2858 (5)	0.4534 (3)	−0.1199 (3)	0.0669 (12)
H5A	−0.3507	0.4675	−0.0760	0.080*
C6	−0.2070 (4)	0.5187 (3)	−0.1626 (3)	0.0502 (10)
C7	−0.2789 (4)	0.6705 (2)	−0.0990 (2)	0.0508 (10)
H7A	−0.3658	0.6415	−0.0799	0.061*
H7B	−0.3047	0.7248	−0.1308	0.061*
C8	−0.1931 (4)	0.6963 (2)	−0.0194 (2)	0.0430 (9)
H8A	−0.1022	0.7221	−0.0379	0.052*
C9	−0.2747 (4)	0.7649 (2)	0.0346 (3)	0.0433 (9)
C10	−0.2528 (4)	0.8626 (2)	0.0197 (2)	0.0433 (9)
C11	−0.1516 (5)	0.8960 (3)	−0.0356 (3)	0.0705 (13)
H11A	−0.0911	0.8566	−0.0649	0.085*
C12	−0.1383 (5)	0.9887 (3)	−0.0485 (3)	0.0804 (15)
H12A	−0.0683	1.0103	−0.0860	0.097*
C13	−0.2257 (5)	1.0486 (2)	−0.0072 (3)	0.0656 (12)
C14	−0.3253 (5)	1.0147 (3)	0.0490 (3)	0.0650 (13)
H14A	−0.3849	1.0542	0.0789	0.078*
C15	−0.3386 (4)	0.9232 (2)	0.0622 (3)	0.0545 (10)
H15A	−0.4073	0.9020	0.1009	0.065*
C16	−0.2116 (6)	1.1492 (3)	−0.0229 (4)	0.0990 (18)
H16A	−0.2517	1.1628	−0.0800	0.119*
H16B	−0.2687	1.1803	0.0205	0.119*
C17	−0.0676 (6)	1.1865 (3)	−0.0198 (4)	0.109 (2)
H17A	−0.0709	1.2501	−0.0311	0.164*
H17B	−0.0099	1.1575	−0.0634	0.164*
H17C	−0.0276	1.1761	0.0373	0.164*
C18	−0.0826 (4)	0.6257 (2)	0.1005 (2)	0.0443 (9)
C19	−0.0495 (4)	0.5386 (2)	0.1438 (2)	0.0459 (10)
C20	−0.1196 (5)	0.4611 (2)	0.1187 (3)	0.0602 (11)
H20A	−0.1879	0.4645	0.0748	0.072*
C21	−0.0906 (6)	0.3783 (3)	0.1573 (3)	0.0742 (14)
H21A	−0.1399	0.3270	0.1397	0.089*
C22	0.0106 (6)	0.3724 (3)	0.2212 (3)	0.0772 (14)
H22A	0.0306	0.3170	0.2471	0.093*
C23	0.0820 (5)	0.4473 (3)	0.2466 (3)	0.0840 (15)
H23A	0.1517	0.4428	0.2895	0.101*
C24	0.0519 (5)	0.5315 (3)	0.2090 (3)	0.0589 (11)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1010 (9)	0.0888 (9)	0.0902 (9)	−0.0149 (8)	−0.0451 (8)	0.0174 (8)
O1	0.0570 (15)	0.0334 (13)	0.0505 (15)	0.0011 (12)	−0.0078 (13)	0.0052 (12)
O2	0.0568 (17)	0.0499 (15)	0.0652 (19)	0.0002 (14)	0.0106 (16)	0.0067 (14)
O3	0.0709 (18)	0.0426 (15)	0.0583 (17)	−0.0093 (14)	−0.0145 (15)	0.0040 (14)
N1	0.057 (2)	0.0464 (19)	0.0452 (18)	0.0041 (16)	−0.0044 (17)	−0.0047 (16)
N2	0.074 (2)	0.073 (2)	0.051 (2)	−0.011 (2)	0.004 (2)	0.001 (2)
N3	0.091 (3)	0.086 (3)	0.060 (2)	−0.002 (2)	0.016 (2)	−0.015 (2)
C1	0.078 (3)	0.059 (3)	0.052 (3)	0.005 (3)	−0.005 (2)	−0.011 (2)
C2	0.103 (4)	0.078 (3)	0.060 (3)	0.020 (3)	0.019 (3)	−0.011 (3)
C3	0.131 (5)	0.060 (3)	0.075 (3)	0.034 (3)	0.003 (4)	−0.015 (3)
C4	0.108 (4)	0.051 (3)	0.083 (3)	0.006 (3)	−0.014 (3)	−0.001 (3)
C5	0.084 (3)	0.058 (3)	0.059 (3)	0.010 (2)	0.000 (3)	0.001 (2)
C6	0.058 (3)	0.046 (2)	0.046 (2)	0.009 (2)	−0.009 (2)	−0.008 (2)
C7	0.057 (2)	0.045 (2)	0.051 (2)	0.0063 (19)	−0.008 (2)	−0.0040 (19)
C8	0.049 (2)	0.0317 (18)	0.049 (2)	0.0025 (16)	−0.0073 (19)	0.0034 (18)
C9	0.039 (2)	0.046 (2)	0.044 (2)	−0.0013 (18)	−0.006 (2)	−0.0013 (19)
C10	0.049 (2)	0.036 (2)	0.045 (2)	0.0026 (18)	0.0024 (19)	0.0004 (18)
C11	0.088 (3)	0.040 (2)	0.084 (3)	0.009 (2)	0.022 (3)	0.007 (2)
C12	0.094 (4)	0.044 (3)	0.104 (4)	0.000 (3)	0.037 (3)	0.013 (3)
C13	0.069 (3)	0.037 (2)	0.091 (3)	0.003 (2)	−0.009 (3)	−0.002 (2)
C14	0.063 (3)	0.044 (3)	0.088 (3)	0.011 (2)	−0.004 (3)	−0.014 (2)
C15	0.053 (2)	0.050 (2)	0.061 (2)	0.000 (2)	0.001 (2)	−0.004 (2)
C16	0.107 (4)	0.039 (2)	0.151 (5)	−0.004 (3)	−0.003 (4)	0.013 (3)
C17	0.131 (5)	0.053 (3)	0.144 (5)	−0.018 (3)	−0.027 (4)	0.011 (3)
C18	0.044 (2)	0.042 (2)	0.046 (2)	−0.0026 (19)	0.0019 (19)	0.000 (2)
C19	0.057 (2)	0.042 (2)	0.039 (2)	0.007 (2)	0.0058 (19)	0.0021 (18)
C20	0.084 (3)	0.044 (2)	0.053 (2)	0.002 (2)	−0.009 (2)	0.001 (2)
C21	0.109 (4)	0.037 (2)	0.076 (3)	0.000 (3)	0.013 (3)	0.003 (2)
C22	0.101 (4)	0.056 (3)	0.074 (3)	0.021 (3)	0.017 (3)	0.027 (3)
C23	0.092 (4)	0.085 (3)	0.075 (3)	0.019 (3)	−0.014 (3)	0.029 (3)
C24	0.068 (3)	0.054 (2)	0.054 (3)	0.005 (2)	−0.002 (2)	0.012 (2)

Cl1—C24	1.734 (4)	C10—C15	1.373 (5)
O1—C18	1.355 (4)	C11—C12	1.394 (5)
O1—C8	1.448 (4)	C11—H11A	0.9300
O2—C9	1.228 (4)	C12—C13	1.364 (6)
O3—C18	1.191 (4)	C12—H12A	0.9300
N1—N2	1.355 (4)	C13—C14	1.368 (6)
N1—C6	1.361 (4)	C13—C16	1.516 (5)
N1—C7	1.445 (4)	C14—C15	1.378 (5)
N2—N3	1.312 (4)	C14—H14A	0.9300
N3—C1	1.371 (5)	C15—H15A	0.9300
C1—C6	1.380 (6)	C16—C17	1.468 (7)
C1—C2	1.382 (5)	C16—H16A	0.9700
C2—C3	1.348 (6)	C16—H16B	0.9700
C2—H2B	0.9300	C17—H17A	0.9600
C3—C4	1.385 (7)	C17—H17B	0.9600
C3—H3B	0.9300	C17—H17C	0.9600
C4—C5	1.385 (6)	C18—C19	1.483 (5)
C4—H4A	0.9300	C19—C20	1.379 (5)
C5—C6	1.383 (5)	C19—C24	1.383 (6)
C5—H5A	0.9300	C20—C21	1.389 (5)
C7—C8	1.508 (5)	C20—H20A	0.9300
C7—H7A	0.9700	C21—C22	1.367 (7)
C7—H7B	0.9700	C21—H21A	0.9300
C8—C9	1.518 (5)	C22—C23	1.355 (6)
C8—H8A	0.9800	C22—H22A	0.9300
C9—C10	1.480 (5)	C23—C24	1.403 (6)
C10—C11	1.367 (5)	C23—H23A	0.9300

C18—O1—C8	113.8 (2)	C13—C12—C11	121.5 (4)
N2—N1—C6	110.5 (3)	C13—C12—H12A	119.2
N2—N1—C7	119.8 (3)	C11—C12—H12A	119.2
C6—N1—C7	129.8 (3)	C12—C13—C14	117.7 (4)
N3—N2—N1	108.1 (3)	C12—C13—C16	121.0 (5)
N2—N3—C1	108.3 (3)	C14—C13—C16	121.3 (4)
N3—C1—C6	108.9 (4)	C13—C14—C15	121.1 (4)
N3—C1—C2	130.9 (4)	C13—C14—H14A	119.5
C6—C1—C2	120.2 (4)	C15—C14—H14A	119.5
C3—C2—C1	118.4 (4)	C10—C15—C14	121.5 (4)
C3—C2—H2B	120.8	C10—C15—H15A	119.3
C1—C2—H2B	120.8	C14—C15—H15A	119.3
C2—C3—C4	121.2 (4)	C17—C16—C13	116.5 (4)
C2—C3—H3B	119.4	C17—C16—H16A	108.2
C4—C3—H3B	119.4	C13—C16—H16A	108.2
C5—C4—C3	122.1 (5)	C17—C16—H16B	108.2
C5—C4—H4A	118.9	C13—C16—H16B	108.2
C3—C4—H4A	118.9	H16A—C16—H16B	107.3
C6—C5—C4	115.5 (4)	C16—C17—H17A	109.5
C6—C5—H5A	122.3	C16—C17—H17B	109.5
C4—C5—H5A	122.3	H17A—C17—H17B	109.5
N1—C6—C1	104.2 (4)	C16—C17—H17C	109.5
N1—C6—C5	133.1 (4)	H17A—C17—H17C	109.5
C1—C6—C5	122.6 (4)	H17B—C17—H17C	109.5
N1—C7—C8	113.0 (3)	O3—C18—O1	121.4 (3)
N1—C7—H7A	109.0	O3—C18—C19	126.9 (4)
C8—C7—H7A	109.0	O1—C18—C19	111.7 (3)
N1—C7—H7B	109.0	C20—C19—C24	117.9 (3)
C8—C7—H7B	109.0	C20—C19—C18	120.0 (4)
H7A—C7—H7B	107.8	C24—C19—C18	122.1 (3)
O1—C8—C7	107.0 (3)	C19—C20—C21	121.6 (4)
O1—C8—C9	111.0 (3)	C19—C20—H20A	119.2
C7—C8—C9	109.5 (3)	C21—C20—H20A	119.2
O1—C8—H8A	109.8	C22—C21—C20	119.7 (4)
C7—C8—H8A	109.8	C22—C21—H21A	120.1
C9—C8—H8A	109.8	C20—C21—H21A	120.1
O2—C9—C10	121.3 (3)	C23—C22—C21	119.9 (4)
O2—C9—C8	118.4 (3)	C23—C22—H22A	120.0
C10—C9—C8	120.1 (3)	C21—C22—H22A	120.0
C11—C10—C15	117.8 (3)	C22—C23—C24	120.8 (4)
C11—C10—C9	123.1 (3)	C22—C23—H23A	119.6
C15—C10—C9	119.1 (3)	C24—C23—H23A	119.6
C10—C11—C12	120.4 (4)	C19—C24—C23	120.1 (4)
C10—C11—H11A	119.8	C19—C24—Cl1	124.3 (3)
C12—C11—H11A	119.8	C23—C24—Cl1	115.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O3ⁱ	0.97	2.51	3.162 (4)	125
C8—H8A···O2ⁱⁱ	0.98	2.42	3.397 (5)	171
C11—H11A···O2ⁱⁱ	0.93	2.56	3.431 (5)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯O3ⁱ	0.97	2.51	3.162 (4)	125
C8—H8A⋯O2ⁱⁱ	0.98	2.42	3.397 (5)	171
C11—H11A⋯O2ⁱⁱ	0.93	2.56	3.431 (5)	155

Symmetry codes: (i) ; (ii) .

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

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

Authors: Zhong-Yi Chen; Ming-Jung Wu
Journal: Org Lett Date: 2005-02-03 Impact factor: 6.005

2 in total

1 in total

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

Authors: Ting Guo; Gang Cao; Sen Xu
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-04-18

1 in total