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In the title compound, C22H17Cl2NO3S, the mol­ecule is a substituted 3,4-di­hydro-2H-1,4-benzoxazine compound which has three phenyl rings which are essentially planar. The 3,4-di­hydro-2H-oxazine part of the mol­ecule is fused to the benzo ring and has a half-boat conformation; the dihedral angle between the planar part of the oxazine ring and the benzo ring is 10.2 (2)°. The (3-chloro­phenyl)­methyl­idene substituent has a Z configuration in relation to the ring N atom of the oxazine moiety. Interestingly, the p-toluenesulfonyl (p-tosyl) substituent on the ring N atom protrudes away from the 3-­chloro­phenyl substituent thus avoiding any steric interaction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101004036/gd1131sup1.cif
Contains datablocks S833, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101004036/gd1131IIIsup2.hkl
Contains datablock 1

CCDC reference: 166989

Comment top

The 3,4-dihydro-2H-1,4-Benzoxazine, (I), structure has been the integral part of many naturally occurring substances (Sainsbury, 1984). Also, various benzoxazine derivatives have shown interesting pharmacological activities, e.g. anticancer (Sugimoto et al., 1990; Zhen et al., 1989), antiemetic (Fukuda et al., 1991), antitubercular (Hirata et al., 1995) and antirheumatic properties (Matsuoka et al., 1997). \sch

As a continuation of our studies on the synthesis of heterocyclic structures of biological importance (Nandi & Kundu, 2000; Chaudhuri & Kundu, 2000), we have recently reported the synthesis and X-ray structure determination of (Z)—N-benzyl-2,3-dihydro-2- (2-methoxybenzylidene)-4H-1,4-benzoxazine, (II) (Maiti et al., 1999). In the present paper, we describe the synthesis and X-ray structure determination of a 3-alkylidene benzoxazine, namely, (Z)-7-chloro-3-[(3-chlorophenyl)methylidene]-4-p-tosyl-3,4-dihydro- 2H-1,4-benzoxazine, (III).

The geometric parameters determined for (III) show some similarities to those found in (II) (Maiti et al., 1999); the heterocyclic ring adopts a half boat conformation and the planar part of the heterocyclic ring (atoms O1, N1, C6, and C8) forms a dihedral angle with the fused phenyl ring A of 10.2 (2)°, with C1 and C7 on opposite sides of the best plane by 0.085 (3) and 0.611 (4) Å, respectively. This dihedral angle is however somewhat larger than that in (II), which is 4.70 (6)°. A shortening of bond length of atoms adjacent to the phenyl rings A and B due to conjugation, is seen which is particularly marked for the bond-length O1—C6 of 1.361 (3) Å [compared with 1.434 (3) for O1—C7]. The effect of conjugation is less evident for the bond lengths to N1 which are 1.439 (3) and 1.443 (3) Å for N1—C1 and N1—C8, respectively, although these values are still significantly shorter than the N—C single bond length of 1.48 Å (Allen et al.. 1987). The dihedral angles A/B, A/C and B/C are 42.18 (9), 52.49 (8) and 26.9 (1)°, respectively. The geometric parameters of the p-tosyl group and of the chlorophenyl group are within normal bounds, with the p-tosyl group angled away from the 3-chlorophenyl derivative reducing steric hindrance.

Related literature top

For related literature, see: Chaudhuri & Kundu (2000); Fukuda et al. (1991); Hirata et al. (1995); Maiti et al. (1999); Matsuoka et al. (1997); Nandi & Kundu (2000); Sainsbury (1984); Sugimoto et al. (1990); Zhen et al. (1989).

Experimental top

4-Chloro-2-(prop-2'-ynyloxy)aniline was arylated with 3-chloroiodobenzene under palladium-copper catalysis in triethylamine (Kundu et al., 2001). This was converted to the corresponding tosylate with tosyl chloride in presence of pyridine in dichloromethane. The tosylate was then cyclized with CuI in the presence of K2CO3 and tetrabutylammonium bromide in acetonitrile by refluxing at 353 K to yield the title compound, (III), m.p. 428 K. Single crystals suitable for X-ray analysis were obtained from CHCl3/petroleum ether (b.p. 333–353 K) (1:3) by slow crystallization.

Refinement top

H atoms were included in calculated positions with C—H 0.93 to 0.97 Å. The hydrogen atoms bonded to C22 (the p-methyl group) were disordered over two sets of sites, rotated with respect to one another by 60 °. They were modelled using the AFIX 123 command, and assigned occupancies of 0.5 each.

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1995); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: TEXSAN.

Figures top
[Figure 1] Fig. 1. ORTEP (Johnson, 1965) plot of (III) using 50% probability ellipsoids.
(III) top
Crystal data top
C22H17Cl2NO3SZ = 2
Mr = 446.33F(000) = 460
Triclinic, P1Dx = 1.479 Mg m3
a = 10.899 (5) ÅMo Kα radiation, λ = 0.7107 Å
b = 12.211 (4) ÅCell parameters from 20 reflections
c = 7.775 (3) Åθ = 6.8–8.2°
α = 102.23 (2)°µ = 0.45 mm1
β = 92.21 (3)°T = 296 K
γ = 96.64 (3)°Block, colourless
V = 1002.4 (6) Å30.40 × 0.37 × 0.37 mm
Data collection top
Rigaku AFC5R
diffractometer
3158 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anodeRint = 0.018
Graphite monochromatorθmax = 27.6°, θmin = 1.7°
ω–2θ scansh = 014
Absorption correction: ψ scans (north et al., 1968)
?
k = 1515
Tmin = 0.800, Tmax = 0.846l = 1010
4862 measured reflections3 standard reflections every 150 reflections
4619 independent reflections intensity decay: 0.3%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 1.09Calculated w = 1/[σ2(Fo2) + (0.0422P)2 + 0.3626P]
where P = (Fo2 + 2Fc2)/3
4619 reflections(Δ/σ)max = 0.001
262 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C22H17Cl2NO3Sγ = 96.64 (3)°
Mr = 446.33V = 1002.4 (6) Å3
Triclinic, P1Z = 2
a = 10.899 (5) ÅMo Kα radiation
b = 12.211 (4) ŵ = 0.45 mm1
c = 7.775 (3) ÅT = 296 K
α = 102.23 (2)°0.40 × 0.37 × 0.37 mm
β = 92.21 (3)°
Data collection top
Rigaku AFC5R
diffractometer
3158 reflections with I > 2σ(I)
Absorption correction: ψ scans (north et al., 1968)
?
Rint = 0.018
Tmin = 0.800, Tmax = 0.8463 standard reflections every 150 reflections
4862 measured reflections intensity decay: 0.3%
4619 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.118H-atom parameters constrained
S = 1.09Δρmax = 0.33 e Å3
4619 reflectionsΔρmin = 0.22 e Å3
262 parameters
Special details top

Experimental. The scan width was (1.15 + 0.30tanθ)° with an ω scan speed of 10° per minute (up to 4 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

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.

Table of Least-Squares Planes ——————————

————– Plane number 1 —————

Atoms Defining Plane Distance C(1) (1) -0.0174 C(2) (1) 0.0206 C(3) (1) -0.0061 C(4) (1) -0.0115 C(5) (1) 0.0142 C(6) (1) 0.0002

Mean deviation from plane is 0.0117 angstroms Chi-squared: 0.0

————– Plane number 2 —————

Atoms Defining Plane Distance O(1) (1) -0.0016 N(1) (1) 0.0014 C(1) (1) -0.0031 C(6) (1) 0.0032

Additional Atoms Distance C(7) (1) -0.3713 C(8) (1) 0.3256

Mean deviation from plane is 0.0023 angstroms Chi-squared: 0.0

Dihedral angles between least-squares planes plane plane angle 2 1 2.22

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
xyzUiso*/UeqOcc. (<1)
Cl10.60753 (9)0.47686 (8)0.28836 (13)0.0776 (3)
Cl20.16901 (8)1.25696 (7)0.16951 (11)0.0661 (2)
S10.26517 (6)0.92383 (5)0.51062 (8)0.03593 (16)
O10.22911 (16)0.63114 (14)0.1063 (2)0.0470 (5)
O20.37269 (16)0.94479 (15)0.6270 (2)0.0478 (5)
O30.20554 (17)1.01453 (14)0.4742 (2)0.0478 (5)
N10.30633 (17)0.85392 (16)0.3145 (2)0.0338 (4)
C10.3788 (2)0.7624 (2)0.3124 (3)0.0346 (5)
C20.4938 (2)0.7797 (2)0.4019 (3)0.0416 (6)
H20.52460.85150.46620.050*
C30.5632 (3)0.6920 (2)0.3971 (4)0.0495 (7)
H30.63900.70350.46170.059*
C40.5198 (3)0.5879 (2)0.2963 (4)0.0484 (7)
C50.4092 (3)0.5688 (2)0.1995 (4)0.0468 (6)
H50.38240.49800.12850.056*
C60.3373 (2)0.6562 (2)0.2081 (3)0.0381 (6)
C70.1435 (2)0.7123 (2)0.1472 (3)0.0404 (6)
H7A0.10340.70330.25350.049*
H7B0.08010.69980.05160.049*
C80.2104 (2)0.8296 (2)0.1736 (3)0.0356 (5)
C90.1884 (2)0.8997 (2)0.0715 (3)0.0386 (6)
H90.12070.87390.00930.046*
C100.2513 (2)1.0107 (2)0.0623 (3)0.0372 (5)
C110.1902 (2)1.0758 (2)0.0310 (3)0.0403 (6)
H110.10991.05020.07930.048*
C120.2479 (2)1.1778 (2)0.0521 (3)0.0422 (6)
C130.3669 (3)1.2175 (2)0.0145 (4)0.0522 (7)
H130.40531.28630.00180.063*
C140.4282 (3)1.1528 (3)0.1060 (4)0.0563 (8)
H140.50911.17830.15170.068*
C150.3716 (2)1.0514 (2)0.1309 (4)0.0481 (7)
H150.41431.00940.19420.058*
C160.1555 (2)0.8288 (2)0.5823 (3)0.0358 (5)
C170.0320 (2)0.8437 (2)0.5768 (3)0.0453 (6)
H170.00710.90640.54180.054*
C180.0539 (3)0.7655 (3)0.6232 (4)0.0526 (7)
H180.13680.77680.62190.063*
C190.0195 (3)0.6704 (2)0.6717 (4)0.0522 (7)
C200.1046 (3)0.6577 (2)0.6780 (4)0.0517 (7)
H200.12930.59470.71250.062*
C210.1931 (2)0.7359 (2)0.6345 (3)0.0431 (6)
H210.27650.72630.64030.052*
C220.1147 (4)0.5833 (3)0.7161 (5)0.0831 (12)
H22A0.07440.52350.74660.125*0.50
H22B0.17210.55310.61600.125*0.50
H22C0.15830.61760.81410.125*0.50
H22D0.19550.60600.70460.125*0.50
H22E0.09770.57640.83510.125*0.50
H22F0.11160.51190.63700.125*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0802 (6)0.0717 (6)0.0954 (7)0.0454 (5)0.0147 (5)0.0299 (5)
Cl20.0673 (5)0.0728 (5)0.0754 (5)0.0307 (4)0.0108 (4)0.0417 (4)
S10.0397 (3)0.0328 (3)0.0349 (3)0.0061 (3)0.0009 (3)0.0058 (2)
O10.0453 (11)0.0366 (10)0.0537 (11)0.0043 (8)0.0033 (9)0.0005 (8)
O20.0449 (10)0.0533 (11)0.0392 (10)0.0009 (9)0.0043 (8)0.0006 (8)
O30.0615 (12)0.0342 (10)0.0505 (11)0.0148 (9)0.0063 (9)0.0107 (8)
N10.0347 (11)0.0344 (10)0.0321 (10)0.0043 (8)0.0003 (8)0.0077 (8)
C10.0356 (13)0.0365 (13)0.0342 (13)0.0063 (10)0.0082 (10)0.0113 (10)
C20.0358 (14)0.0444 (14)0.0444 (14)0.0051 (11)0.0026 (11)0.0092 (11)
C30.0390 (14)0.0642 (19)0.0507 (16)0.0160 (13)0.0040 (12)0.0192 (14)
C40.0517 (17)0.0487 (16)0.0538 (17)0.0222 (13)0.0170 (14)0.0203 (13)
C50.0529 (17)0.0361 (14)0.0538 (16)0.0093 (12)0.0123 (14)0.0115 (12)
C60.0358 (13)0.0389 (14)0.0399 (14)0.0029 (11)0.0073 (11)0.0093 (11)
C70.0353 (13)0.0433 (14)0.0409 (14)0.0025 (11)0.0000 (11)0.0069 (11)
C80.0337 (13)0.0378 (13)0.0339 (13)0.0062 (10)0.0005 (10)0.0041 (10)
C90.0370 (13)0.0442 (14)0.0333 (13)0.0071 (11)0.0029 (10)0.0057 (11)
C100.0402 (14)0.0404 (13)0.0320 (12)0.0081 (11)0.0001 (11)0.0087 (10)
C110.0369 (14)0.0508 (16)0.0359 (13)0.0120 (12)0.0028 (11)0.0116 (11)
C120.0494 (16)0.0447 (15)0.0378 (14)0.0181 (12)0.0062 (12)0.0140 (11)
C130.0614 (19)0.0454 (16)0.0508 (17)0.0009 (14)0.0037 (14)0.0161 (13)
C140.0495 (17)0.0598 (19)0.0596 (18)0.0067 (14)0.0101 (14)0.0231 (15)
C150.0453 (16)0.0561 (17)0.0463 (16)0.0050 (13)0.0074 (12)0.0214 (13)
C160.0416 (14)0.0355 (13)0.0298 (12)0.0062 (10)0.0020 (10)0.0056 (10)
C170.0424 (15)0.0506 (16)0.0455 (15)0.0108 (13)0.0011 (12)0.0140 (12)
C180.0390 (15)0.0651 (19)0.0503 (17)0.0011 (14)0.0026 (13)0.0080 (14)
C190.0633 (19)0.0462 (16)0.0400 (15)0.0085 (14)0.0113 (14)0.0007 (12)
C200.074 (2)0.0388 (15)0.0466 (16)0.0104 (14)0.0147 (15)0.0144 (12)
C210.0475 (15)0.0439 (15)0.0417 (14)0.0149 (12)0.0070 (12)0.0120 (12)
C220.092 (3)0.072 (2)0.073 (2)0.025 (2)0.027 (2)0.0044 (19)
Geometric parameters (Å, º) top
Cl1—C41.740 (3)C10—C151.390 (4)
Cl2—C121.735 (3)C11—C121.374 (4)
S1—O21.4169 (19)C11—H110.9300
S1—O31.4191 (18)C12—C131.372 (4)
S1—N11.687 (2)C13—C141.378 (4)
S1—C161.758 (3)C13—H130.9300
O1—C61.361 (3)C14—C151.373 (4)
O1—C71.434 (3)C14—H140.9300
N1—C11.439 (3)C15—H150.9300
N1—C81.443 (3)C16—C171.379 (3)
C1—C21.382 (3)C16—C211.382 (3)
C1—C61.391 (3)C17—C181.373 (4)
C2—C31.377 (3)C17—H170.9300
C2—H20.9300C18—C191.380 (4)
C3—C41.365 (4)C18—H180.9300
C3—H30.9300C19—C201.380 (4)
C4—C51.365 (4)C19—C221.502 (4)
C5—C61.387 (3)C20—C211.380 (4)
C5—H50.9300C20—H200.9300
C7—C81.499 (3)C21—H210.9300
C7—H7A0.9700C22—H22A0.9600
C7—H7B0.9700C22—H22B0.9600
C8—C91.320 (3)C22—H22C0.9600
C9—C101.464 (3)C22—H22D0.9600
C9—H90.9300C22—H22E0.9600
C10—C111.389 (3)C22—H22F0.9600
O2—S1—O3120.68 (12)C12—C13—C14118.3 (3)
O2—S1—N1106.29 (11)C12—C13—H13120.8
O3—S1—N1105.86 (10)C14—C13—H13120.8
O2—S1—C16108.54 (12)C15—C14—C13121.0 (3)
O3—S1—C16108.71 (12)C15—C14—H14119.5
N1—S1—C16105.79 (11)C13—C14—H14119.5
C6—O1—C7114.86 (19)C14—C15—C10120.7 (2)
C1—N1—C8112.98 (18)C14—C15—H15119.7
C1—N1—S1118.36 (15)C10—C15—H15119.7
C8—N1—S1115.05 (15)C17—C16—C21120.4 (2)
C2—C1—C6118.8 (2)C17—C16—S1120.01 (19)
C2—C1—N1121.2 (2)C21—C16—S1119.46 (19)
C6—C1—N1119.8 (2)C18—C17—C16119.7 (3)
C3—C2—C1120.8 (3)C18—C17—H17120.2
C3—C2—H2119.6C16—C17—H17120.2
C1—C2—H2119.6C17—C18—C19121.3 (3)
C4—C3—C2119.3 (3)C17—C18—H18119.4
C4—C3—H3120.4C19—C18—H18119.4
C2—C3—H3120.4C18—C19—C20118.1 (3)
C3—C4—C5121.6 (2)C18—C19—C22120.9 (3)
C3—C4—Cl1119.6 (2)C20—C19—C22121.0 (3)
C5—C4—Cl1118.9 (2)C19—C20—C21121.8 (3)
C4—C5—C6119.3 (3)C19—C20—H20119.1
C4—C5—H5120.4C21—C20—H20119.1
C6—C5—H5120.4C20—C21—C16118.7 (2)
O1—C6—C5115.9 (2)C20—C21—H21120.6
O1—C6—C1124.0 (2)C16—C21—H21120.6
C5—C6—C1120.1 (2)C19—C22—H22A109.5
O1—C7—C8109.9 (2)C19—C22—H22B109.5
O1—C7—H7A109.7H22A—C22—H22B109.5
C8—C7—H7A109.7C19—C22—H22C109.5
O1—C7—H7B109.7H22A—C22—H22C109.5
C8—C7—H7B109.7H22B—C22—H22C109.5
H7A—C7—H7B108.2C19—C22—H22D109.5
C9—C8—N1124.1 (2)H22A—C22—H22D141.1
C9—C8—C7123.2 (2)H22B—C22—H22D56.3
N1—C8—C7112.6 (2)H22C—C22—H22D56.3
C8—C9—C10131.6 (2)C19—C22—H22E109.5
C8—C9—H9114.2H22A—C22—H22E56.3
C10—C9—H9114.2H22B—C22—H22E141.1
C11—C10—C15118.2 (2)H22C—C22—H22E56.3
C11—C10—C9117.9 (2)H22D—C22—H22E109.5
C15—C10—C9123.8 (2)C19—C22—H22F109.5
C12—C11—C10120.2 (2)H22A—C22—H22F56.3
C12—C11—H11119.9H22B—C22—H22F56.3
C10—C11—H11119.9H22C—C22—H22F141.1
C13—C12—C11121.6 (2)H22D—C22—H22F109.5
C13—C12—Cl2119.3 (2)H22E—C22—H22F109.5
C11—C12—Cl2119.1 (2)
O2—S1—N1—C145.3 (2)O1—C7—C8—N159.4 (3)
O3—S1—N1—C1174.74 (17)N1—C8—C9—C103.4 (4)
C16—S1—N1—C169.99 (19)C7—C8—C9—C10172.3 (2)
O2—S1—N1—C8176.83 (16)C8—C9—C10—C11165.4 (3)
O3—S1—N1—C847.36 (19)C8—C9—C10—C1519.2 (4)
C16—S1—N1—C867.90 (18)C15—C10—C11—C120.7 (4)
C8—N1—C1—C2161.6 (2)C9—C10—C11—C12176.3 (2)
S1—N1—C1—C259.7 (3)C10—C11—C12—C131.2 (4)
C8—N1—C1—C613.5 (3)C10—C11—C12—Cl2179.95 (18)
S1—N1—C1—C6125.2 (2)C11—C12—C13—C140.7 (4)
C6—C1—C2—C33.9 (4)Cl2—C12—C13—C14179.5 (2)
N1—C1—C2—C3179.1 (2)C12—C13—C14—C150.3 (5)
C1—C2—C3—C42.8 (4)C13—C14—C15—C100.7 (5)
C2—C3—C4—C50.3 (4)C11—C10—C15—C140.3 (4)
C2—C3—C4—Cl1179.6 (2)C9—C10—C15—C14175.1 (3)
C3—C4—C5—C62.1 (4)O2—S1—C16—C17139.9 (2)
Cl1—C4—C5—C6178.56 (19)O3—S1—C16—C176.9 (2)
C7—O1—C6—C5166.0 (2)N1—S1—C16—C17106.4 (2)
C7—O1—C6—C115.8 (3)O2—S1—C16—C2143.7 (2)
C4—C5—C6—O1179.2 (2)O3—S1—C16—C21176.70 (19)
C4—C5—C6—C10.9 (4)N1—S1—C16—C2170.0 (2)
C2—C1—C6—O1176.1 (2)C21—C16—C17—C180.1 (4)
N1—C1—C6—O10.9 (4)S1—C16—C17—C18176.2 (2)
C2—C1—C6—C52.0 (4)C16—C17—C18—C191.5 (4)
N1—C1—C6—C5177.2 (2)C17—C18—C19—C202.1 (4)
C6—O1—C7—C844.2 (3)C17—C18—C19—C22177.8 (3)
C1—N1—C8—C9133.0 (2)C18—C19—C20—C211.1 (4)
S1—N1—C8—C986.9 (3)C22—C19—C20—C21178.8 (3)
C1—N1—C8—C743.1 (3)C19—C20—C21—C160.4 (4)
S1—N1—C8—C797.1 (2)C17—C16—C21—C201.1 (4)
O1—C7—C8—C9116.7 (3)S1—C16—C21—C20175.3 (2)

Experimental details

Crystal data
Chemical formulaC22H17Cl2NO3S
Mr446.33
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)10.899 (5), 12.211 (4), 7.775 (3)
α, β, γ (°)102.23 (2), 92.21 (3), 96.64 (3)
V3)1002.4 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.45
Crystal size (mm)0.40 × 0.37 × 0.37
Data collection
DiffractometerRigaku AFC5R
diffractometer
Absorption correctionψ scans (North et al., 1968)
Tmin, Tmax0.800, 0.846
No. of measured, independent and
observed [I > 2σ(I)] reflections
4862, 4619, 3158
Rint0.018
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.118, 1.09
No. of reflections4619
No. of parameters262
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.22

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1995), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1995), SHELXS86 (Sheldrick, 1985), SHELXL97 (Sheldrick, 1997), TEXSAN.

 

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