3-Benzyl-6-(2-chloro­benzo­yl)-1,3-benzoxazol-2(3H)-one

Takhirov, Y.R.; Dushamov, D.A.; Turgunov, K.K.; Mukhamedov, N.S.; Shakhidoyatov, K.M.

doi:10.1107/S1600536810046301

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3203

https://doi.org/10.1107/S1600536810046301

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3-Benzyl-6-(2-chlorobenzoyl)-1,3-benzoxazol-2(3H)-one

Yuldash R. Takhirov,^a ^* Dilshod A. Dushamov,^a Kambarali K. Turgunov,^b Nasirkhon S. Mukhamedov ^b and Khusniddin M. Shakhidoyatov ^b

^aUrgench State University named after Al-Khorezmiy, Kh. Olimjon Str. 14, Urgench 220100, Uzbekistan, and ^bS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent 100170, Uzbekistan
^*Correspondence e-mail: yuldash_78@mail.ru

(Received 23 September 2010; accepted 9 November 2010; online 17 November 2010)

In the title compound, C₂₁H₁₄ClNO₃, the benzoxazolone ring system is planar (r.m.s. deviation = 0.022 Å) and forms dihedral angles of 75.38 (10) and 65.92 (13)° with the mean planes of the chlorobenzoyl (r.m.s. deviation = 0.045 Å, excluding O atom) and benzyl (r.m.s. deviation = 0.023 Å) groups. The observed structure is stabilized by weak C—H⋯O hydrogen bonds and weak intermolecular C—H⋯π interactions.

Related literature

For the natural source of benzoxazolin-2-one and its derivatives, see: Tang et al. (1975 ); Chen & Chen (1976 ); Smissman et al. (1957 ). For the synthesis of benzoxazolin-2-one derivatives, see: Honkanen & Virtanen (1961 ); Bredenberg et al. (1962 ); Mukhamedov et al. (1994 ). For related structures, see: Groth (1973 ); Işık et al. (2004 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₁H₁₄ClNO₃
M_r = 363.78
Monoclinic, P 2₁ /n
a = 13.391 (7) Å
b = 7.317 (6) Å
c = 18.611 (9) Å
β = 109.72 (4)°
V = 1716.6 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 293 K
0.80 × 0.40 × 0.07 mm

Data collection

Stoe Stadi-4 four-circle diffractometer
3452 measured reflections
2987 independent reflections
1866 reflections with I > 2σ(I)
R_int = 0.099
3 standard reflections every 60 min intensity decay: 3.7%

Refinement

R[F² > 2σ(F²)] = 0.072
wR(F²) = 0.205
S = 1.06
2987 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C16–C21 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O2ⁱ	0.93	2.59	3.266 (8)	130
C20—H20A⋯O3ⁱ	0.93	2.59	3.269 (8)	130
C11—H11A⋯Cg1ⁱⁱ	0.93	2.92	3.474 (7)	119
Symmetry codes: (i) x, y-1, z; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: STADI4 (Stoe & Cie, 1997 ); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Bruker, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810046301/jj2063sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810046301/jj2063Isup2.hkl

checkCIF report

Comment top

Benzoxazolin-2-one and its derivatives were found in rye seedlings, roots of Coix Lacryma Jobi L. and Scoporia dulcus and possess physiological activity (Tang et al., 1975; Chen & Chen, 1976; Smissman et al., 1957). Acylation of benzoxazolin-2-ones using FeCl₃^.6H₂O as a catalyst, in low yields, has been demonstrated (Mukhamedov et al., 1994). Our efforts toward acylation of benzoxazolin-2-one derivatives, containing an additional aromatic ring, has led to the synthesis of the title compound, (I), C₂₁H₁₄ClNO₃.

In the title compound,(I), the benzoxazolone ring system is planar with an r.m.s. deviation of 0.022 Å. The dihedral angles between the mean planes of the benzoxazolone ring system and benzyl plane (r.m.s.deviation of 0.023Å) is 65.92 (13)° (Fig. 2). The carbonyl group is twisted by 61.6 (3)° relative to the mean plane of the chlorophenyl group. The dihedral angle between the benzoxazolone ring system and chlorophenyl plane (r.m.s. deviation of 0.045 Å) is 75.38 (10)°. Bond distances and angles are in normal ranges (Allen et al., 1987). The observed structure is stabilized by weak C—H···O hydrogen bonds (Table 1). In addition, weak C–H···π-ring intermolecular interactions are also observed (Fig. 3) [H11A···Cg1ⁱⁱ = 2.92Å; C11···Cg1ⁱⁱ = 3.474 (7)Å; C11—H11A···Cg1ⁱⁱ = 119°; where Cg1 = C16–C21; ⁱⁱ = -1/2 +x, 1/2 - y, 1/2 + z].

Related literature top

For the natural source of benzoxazolin-2-one and its derivatives, see: Tang et al. (1975); Chen & Chen (1976); Smissman et al. (1957). For the synthesis of benzoxazolin-2-one derivatives, see: Honkanen et al. (1961); Bredenberg et al. (1962); Mukhamedov et al. (1994). For related structures, see: Groth (1973); Işık et al. (2004). For bond-length data, see: Allen et al. (1987).

Experimental top

To a powder of 3-benzylbenzoxazolin-2-one (2.25 g, 10 mmol) was added 2-chloro-benzoylchloride (2.625 g, 1.899 ml, d=1.382 g/ml, 15 mmol) and FeCl₃.6H₂O (0,027 g, 0.1 mmol) as a catalyst (Fig. 1). The reaction mixture was heated to 423–433 K for 4 h. After cooling, the product was washed with water and re-crystallized from ethanol. The title compound with m.p. 401–403 K was obtained in a yield of 80% (3.2 g). Crystals suitable for X-ray analysis were obtained from ethanol by slow evaporation.

Structure description top

For the natural source of benzoxazolin-2-one and its derivatives, see: Tang et al. (1975); Chen & Chen (1976); Smissman et al. (1957). For the synthesis of benzoxazolin-2-one derivatives, see: Honkanen et al. (1961); Bredenberg et al. (1962); Mukhamedov et al. (1994). For related structures, see: Groth (1973); Işık et al. (2004). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: STADI4 (Stoe & Cie, 1997); cell refinement: STADI4 (Stoe & Cie, 1997); data reduction: X-RED (Stoe & Cie, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Bruker, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The reaction scheme for (I).
	Fig. 2. The molecular structure of the title compound,(I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 3. Packing diagram of the title compound, showing weak C—H···O hydrogen bonds and weak C–H···π-ring intermolecular interactions (dashed lines).

3-Benzyl-6-(2-chlorobenzoyl)-1,3-benzoxazol-2(3H)-one top

Crystal data top

C₂₁H₁₄ClNO₃	F(000) = 752
M_r = 363.78	D_x = 1.408 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 401(2) K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 13.391 (7) Å	Cell parameters from 32 reflections
b = 7.317 (6) Å	θ = 5–15°
c = 18.611 (9) Å	µ = 0.24 mm⁻¹
β = 109.72 (4)°	T = 293 K
V = 1716.6 (19) Å³	Plate, colourless
Z = 4	0.80 × 0.40 × 0.07 mm

Data collection top

Stoe Stadi-4 four-circle diffractometer	R_int = 0.099
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 1.6°
Graphite monochromator	h = −15→14
Scan width (ω) = 0.90 – 1.71, scan ratio 2θ:ω = 1.00 I(Net) and sigma(I) calculated according to Blessing (1987)	k = 0→8
3452 measured reflections	l = 0→22
2987 independent reflections	3 standard reflections every 60 min
1866 reflections with I > 2σ(I)	intensity decay: 3.7%

Refinement top

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.205	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0725P)² + 2.8897P] where P = (F_o² + 2F_c²)/3
2987 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₂₁H₁₄ClNO₃	V = 1716.6 (19) Å³
M_r = 363.78	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.391 (7) Å	µ = 0.24 mm⁻¹
b = 7.317 (6) Å	T = 293 K
c = 18.611 (9) Å	0.80 × 0.40 × 0.07 mm
β = 109.72 (4)°

Data collection top

Stoe Stadi-4 four-circle diffractometer	R_int = 0.099
3452 measured reflections	3 standard reflections every 60 min
2987 independent reflections	intensity decay: 3.7%
1866 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.072	0 restraints
wR(F²) = 0.205	H-atom parameters constrained
S = 1.06	Δρ_max = 0.28 e Å⁻³
2987 reflections	Δρ_min = −0.32 e Å⁻³
235 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.88491 (10)	0.2399 (2)	0.04201 (8)	0.0687 (4)
O1	0.6161 (3)	0.7278 (4)	0.13219 (19)	0.0572 (9)
O2	0.6094 (3)	0.8327 (5)	0.2452 (2)	0.0766 (11)
O3	0.6181 (3)	0.3656 (5)	−0.10981 (19)	0.0663 (10)
C2	0.6132 (4)	0.7045 (7)	0.2053 (3)	0.0559 (12)
N3	0.6172 (3)	0.5233 (5)	0.2211 (2)	0.0519 (10)
C4A	0.6211 (3)	0.4250 (6)	0.1587 (3)	0.0490 (11)
C4	0.6275 (3)	0.2415 (6)	0.1450 (3)	0.0489 (11)
H4A	0.6262	0.1538	0.1808	0.059*
C5	0.6361 (3)	0.1930 (6)	0.0752 (3)	0.0506 (11)
H5A	0.6400	0.0699	0.0640	0.061*
C6	0.6391 (3)	0.3256 (6)	0.0204 (2)	0.0460 (11)
C7	0.6294 (3)	0.5111 (6)	0.0358 (3)	0.0500 (11)
H7A	0.6283	0.6010	0.0002	0.060*
C7A	0.6219 (3)	0.5538 (6)	0.1039 (3)	0.0485 (11)
C8	0.6265 (4)	0.4485 (8)	0.2965 (3)	0.0615 (13)
H8A	0.6485	0.5460	0.3339	0.074*
H8B	0.6821	0.3568	0.3101	0.074*
C9	0.5278 (4)	0.3645 (6)	0.3019 (2)	0.0497 (11)
C10	0.4392 (4)	0.4682 (7)	0.2953 (3)	0.0591 (13)
H10A	0.4387	0.5917	0.2833	0.071*
C11	0.3516 (4)	0.3913 (9)	0.3061 (3)	0.0722 (16)
H11A	0.2927	0.4633	0.3021	0.087*
C12	0.3507 (5)	0.2090 (9)	0.3226 (3)	0.0807 (17)
H12A	0.2914	0.1570	0.3297	0.097*
C13	0.4371 (6)	0.1042 (8)	0.3286 (3)	0.0806 (17)
H13A	0.4360	−0.0200	0.3390	0.097*
C14	0.5260 (5)	0.1800 (8)	0.3196 (3)	0.0698 (15)
H14A	0.5852	0.1076	0.3253	0.084*
C15	0.6501 (3)	0.2713 (6)	−0.0531 (2)	0.0451 (10)
C16	0.7044 (4)	0.0938 (6)	−0.0560 (3)	0.0505 (11)
C17	0.8106 (4)	0.0622 (7)	−0.0113 (3)	0.0518 (11)
C18	0.8569 (5)	−0.1045 (8)	−0.0133 (3)	0.0679 (15)
H18A	0.9267	−0.1260	0.0175	0.081*
C19	0.8000 (6)	−0.2389 (8)	−0.0608 (4)	0.0817 (19)
H19A	0.8317	−0.3515	−0.0617	0.098*
C20	0.6969 (6)	−0.2108 (8)	−0.1073 (3)	0.0741 (17)
H20A	0.6593	−0.3025	−0.1398	0.089*
C21	0.6500 (5)	−0.0431 (7)	−0.1046 (3)	0.0653 (14)
H21A	0.5806	−0.0224	−0.1362	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0556 (7)	0.0825 (10)	0.0667 (8)	−0.0025 (7)	0.0188 (6)	−0.0065 (7)
O1	0.070 (2)	0.0443 (19)	0.067 (2)	−0.0005 (15)	0.0354 (17)	−0.0036 (16)
O2	0.093 (3)	0.063 (2)	0.084 (3)	0.004 (2)	0.043 (2)	−0.019 (2)
O3	0.080 (2)	0.071 (2)	0.051 (2)	0.0075 (19)	0.0250 (17)	0.0077 (18)
C2	0.047 (3)	0.057 (3)	0.064 (3)	−0.001 (2)	0.019 (2)	−0.010 (3)
N3	0.057 (2)	0.050 (2)	0.052 (2)	0.0041 (18)	0.0221 (18)	−0.0039 (18)
C4A	0.044 (3)	0.049 (3)	0.058 (3)	0.002 (2)	0.022 (2)	0.000 (2)
C4	0.050 (3)	0.046 (3)	0.055 (3)	0.000 (2)	0.023 (2)	0.002 (2)
C5	0.052 (3)	0.049 (3)	0.057 (3)	−0.001 (2)	0.027 (2)	−0.002 (2)
C6	0.044 (2)	0.047 (3)	0.049 (3)	0.003 (2)	0.019 (2)	0.005 (2)
C7	0.050 (3)	0.049 (3)	0.056 (3)	−0.001 (2)	0.025 (2)	0.007 (2)
C7A	0.048 (3)	0.044 (3)	0.060 (3)	0.000 (2)	0.027 (2)	−0.002 (2)
C8	0.052 (3)	0.080 (4)	0.050 (3)	0.010 (3)	0.015 (2)	−0.009 (3)
C9	0.057 (3)	0.054 (3)	0.041 (2)	0.002 (2)	0.020 (2)	−0.005 (2)
C10	0.059 (3)	0.062 (3)	0.062 (3)	0.010 (2)	0.027 (2)	−0.002 (2)
C11	0.069 (4)	0.097 (5)	0.060 (3)	0.002 (3)	0.034 (3)	−0.013 (3)
C12	0.091 (5)	0.087 (5)	0.075 (4)	−0.022 (4)	0.041 (3)	−0.007 (3)
C13	0.115 (5)	0.059 (4)	0.077 (4)	−0.009 (4)	0.045 (4)	0.006 (3)
C14	0.096 (4)	0.059 (3)	0.063 (3)	0.013 (3)	0.038 (3)	0.000 (3)
C15	0.041 (2)	0.058 (3)	0.040 (2)	−0.001 (2)	0.0185 (18)	0.003 (2)
C16	0.056 (3)	0.052 (3)	0.053 (3)	−0.003 (2)	0.031 (2)	−0.001 (2)
C17	0.059 (3)	0.056 (3)	0.049 (3)	0.001 (2)	0.028 (2)	0.001 (2)
C18	0.082 (4)	0.064 (4)	0.071 (4)	0.016 (3)	0.044 (3)	0.009 (3)
C19	0.122 (6)	0.049 (3)	0.102 (5)	0.013 (4)	0.073 (5)	0.006 (3)
C20	0.119 (5)	0.060 (4)	0.066 (4)	−0.022 (3)	0.059 (4)	−0.015 (3)
C21	0.075 (4)	0.064 (4)	0.064 (3)	−0.015 (3)	0.033 (3)	−0.013 (3)

Geometric parameters (Å, º) top

Cl1—C17	1.732 (5)	C9—C14	1.392 (7)
O1—C2	1.384 (6)	C10—C11	1.376 (7)
O1—C7A	1.390 (5)	C10—H10A	0.9300
O2—C2	1.209 (6)	C11—C12	1.370 (8)
O3—C15	1.212 (5)	C11—H11A	0.9300
C2—N3	1.355 (6)	C12—C13	1.360 (9)
N3—C4A	1.381 (6)	C12—H12A	0.9300
N3—C8	1.472 (6)	C13—C14	1.374 (8)
C4A—C4	1.375 (6)	C13—H13A	0.9300
C4A—C7A	1.392 (6)	C14—H14A	0.9300
C4—C5	1.388 (6)	C15—C16	1.498 (6)
C4—H4A	0.9300	C16—C21	1.381 (7)
C5—C6	1.417 (6)	C16—C17	1.403 (6)
C5—H5A	0.9300	C17—C18	1.375 (7)
C6—C7	1.402 (6)	C18—C19	1.370 (8)
C6—C15	1.480 (6)	C18—H18A	0.9300
C7—C7A	1.341 (6)	C19—C20	1.375 (9)
C7—H7A	0.9300	C19—H19A	0.9300
C8—C9	1.491 (7)	C20—C21	1.386 (8)
C8—H8A	0.9700	C20—H20A	0.9300
C8—H8B	0.9700	C21—H21A	0.9300
C9—C10	1.378 (6)

C2—O1—C7A	106.5 (4)	C11—C10—H10A	119.6
O2—C2—N3	129.2 (5)	C9—C10—H10A	119.6
O2—C2—O1	122.0 (5)	C12—C11—C10	120.2 (6)
N3—C2—O1	108.8 (4)	C12—C11—H11A	119.9
C2—N3—C4A	109.7 (4)	C10—C11—H11A	119.9
C2—N3—C8	123.8 (4)	C13—C12—C11	119.7 (6)
C4A—N3—C8	126.3 (4)	C13—C12—H12A	120.1
C4—C4A—N3	133.4 (4)	C11—C12—H12A	120.1
C4—C4A—C7A	120.5 (4)	C12—C13—C14	120.7 (6)
N3—C4A—C7A	106.0 (4)	C12—C13—H13A	119.7
C4A—C4—C5	117.0 (4)	C14—C13—H13A	119.7
C4A—C4—H4A	121.5	C13—C14—C9	120.4 (5)
C5—C4—H4A	121.5	C13—C14—H14A	119.8
C4—C5—C6	122.0 (4)	C9—C14—H14A	119.8
C4—C5—H5A	119.0	O3—C15—C6	122.4 (4)
C6—C5—H5A	119.0	O3—C15—C16	119.7 (4)
C7—C6—C5	119.3 (4)	C6—C15—C16	117.8 (4)
C7—C6—C15	119.6 (4)	C21—C16—C17	118.2 (5)
C5—C6—C15	121.1 (4)	C21—C16—C15	119.8 (4)
C7A—C7—C6	117.3 (4)	C17—C16—C15	121.9 (4)
C7A—C7—H7A	121.3	C18—C17—C16	120.4 (5)
C6—C7—H7A	121.3	C18—C17—Cl1	120.3 (4)
C7—C7A—O1	127.1 (4)	C16—C17—Cl1	119.2 (4)
C7—C7A—C4A	123.9 (4)	C19—C18—C17	119.8 (6)
O1—C7A—C4A	109.1 (4)	C19—C18—H18A	120.1
N3—C8—C9	115.2 (4)	C17—C18—H18A	120.1
N3—C8—H8A	108.5	C18—C19—C20	121.4 (5)
C9—C8—H8A	108.5	C18—C19—H19A	119.3
N3—C8—H8B	108.5	C20—C19—H19A	119.3
C9—C8—H8B	108.5	C19—C20—C21	118.7 (5)
H8A—C8—H8B	107.5	C19—C20—H20A	120.6
C10—C9—C14	118.1 (5)	C21—C20—H20A	120.6
C10—C9—C8	121.5 (5)	C16—C21—C20	121.4 (6)
C14—C9—C8	120.2 (5)	C16—C21—H21A	119.3
C11—C10—C9	120.9 (5)	C20—C21—H21A	119.3

C7A—O1—C2—O2	179.0 (4)	N3—C8—C9—C14	118.2 (5)
C7A—O1—C2—N3	0.1 (5)	C14—C9—C10—C11	0.2 (7)
O2—C2—N3—C4A	−179.8 (5)	C8—C9—C10—C11	−175.1 (4)
O1—C2—N3—C4A	−1.0 (5)	C9—C10—C11—C12	−0.9 (8)
O2—C2—N3—C8	−5.2 (8)	C10—C11—C12—C13	0.3 (9)
O1—C2—N3—C8	173.6 (4)	C11—C12—C13—C14	1.1 (9)
C2—N3—C4A—C4	178.8 (5)	C12—C13—C14—C9	−1.8 (9)
C8—N3—C4A—C4	4.4 (8)	C10—C9—C14—C13	1.2 (7)
C2—N3—C4A—C7A	1.5 (5)	C8—C9—C14—C13	176.5 (5)
C8—N3—C4A—C7A	−173.0 (4)	C7—C6—C15—O3	−24.5 (6)
N3—C4A—C4—C5	−176.3 (4)	C5—C6—C15—O3	154.4 (4)
C7A—C4A—C4—C5	0.8 (7)	C7—C6—C15—C16	154.7 (4)
C4A—C4—C5—C6	0.5 (6)	C5—C6—C15—C16	−26.4 (6)
C4—C5—C6—C7	−2.2 (6)	O3—C15—C16—C21	−61.6 (6)
C4—C5—C6—C15	178.9 (4)	C6—C15—C16—C21	119.1 (5)
C5—C6—C7—C7A	2.6 (6)	O3—C15—C16—C17	117.3 (5)
C15—C6—C7—C7A	−178.6 (4)	C6—C15—C16—C17	−62.0 (5)
C6—C7—C7A—O1	177.2 (4)	C21—C16—C17—C18	−3.3 (7)
C6—C7—C7A—C4A	−1.3 (7)	C15—C16—C17—C18	177.8 (4)
C2—O1—C7A—C7	−177.9 (4)	C21—C16—C17—Cl1	172.8 (4)
C2—O1—C7A—C4A	0.8 (5)	C15—C16—C17—Cl1	−6.1 (6)
C4—C4A—C7A—C7	−0.4 (7)	C16—C17—C18—C19	1.8 (7)
N3—C4A—C7A—C7	177.4 (4)	Cl1—C17—C18—C19	−174.2 (4)
C4—C4A—C7A—O1	−179.2 (4)	C17—C18—C19—C20	0.3 (8)
N3—C4A—C7A—O1	−1.4 (5)	C18—C19—C20—C21	−0.9 (8)
C2—N3—C8—C9	106.2 (5)	C17—C16—C21—C20	2.8 (7)
C4A—N3—C8—C9	−80.1 (6)	C15—C16—C21—C20	−178.3 (4)
N3—C8—C9—C10	−66.6 (6)	C19—C20—C21—C16	−0.7 (8)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C16–C21 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O2ⁱ	0.93	2.59	3.266 (8)	130
C20—H20A···O3ⁱ	0.93	2.59	3.269 (8)	130
C11—H11A···Cg1ⁱⁱ	0.93	2.92	3.474 (7)	119

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₄ClNO₃
M_r	363.78
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	13.391 (7), 7.317 (6), 18.611 (9)
β (°)	109.72 (4)
V (Å³)	1716.6 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.80 × 0.40 × 0.07

Data collection
Diffractometer	Stoe Stadi-4 four-circle
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3452, 2987, 1866
R_int	0.099
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.205, 1.06
No. of reflections	2987
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.32

Computer programs: STADI4 (Stoe & Cie, 1997), X-RED (Stoe & Cie, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Bruker, 1998).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C16–C21 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O2ⁱ	0.93	2.590	3.266 (8)	130
C20—H20A···O3ⁱ	0.93	2.590	3.269 (8)	130
C11—H11A···Cg1ⁱⁱ	0.93	2.92	3.474 (7)	119

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

Acknowledgements

We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study (grant FA–F3–T012).

References

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