2-Meth­oxy­imino-2-{2-[(2-methyl­phen­oxy)meth­yl]phen­yl}ethanol

Kant, R.; Gupta, V.K.; Kapoor, K.; Shripanavar, C.S.; Banerjee, K.

doi:10.1107/S160053681203499X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2697

doi:10.1107/S160053681203499X

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2-Methoxyimino-2-{2-[(2-methylphenoxy)methyl]phenyl}ethanol

Rajni Kant,^a Vivek K. Gupta,^a Kamini Kapoor,^a Chetan S. Shripanavar ^b and Kaushik Banerjee ^b ^*

^aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and ^bNational Research Centre for Grapes, Pune 412 307, India
^*Correspondence e-mail: rkvk.paper11@gmail.com

(Received 25 July 2012; accepted 8 August 2012; online 11 August 2012)

In the title compound, C₁₇H₁₉NO₃, the dihedral angle between the benzene rings is 68.0 (1)°. The C—O—C—C torsion angle of the atoms joining these rings is 179.7 (2)°. The atoms of the methanol group were refined as disordered over two sets of sites with fixed occupancies of 0.86 and 0.14. The H atoms of the hydroxy group in the major component are disordered over a further two sets of sites with equal occupancies. This is a necessary arrangement to allow for hydrogen bonding without unrealistic H⋯H contacts. In the crystal, O—H⋯N and O—H⋯O hydrogen bonds connect molecules into chains along [001].

Related literature

The title compound was derived from kresoxim-methyl. For the biological activity of kresoxim-methyl, see: Anke et al. (1977 ); Clinton et al. (2011 ); Balba (2007 ); Sudisha et al. (2005 ). For related structures, see: Chopra et al. (2004 ); Kant et al. (2012a ,b ).

Experimental

Crystal data

C₁₇H₁₉NO₃
M_r = 285.33
Monoclinic, C 2/c
a = 21.0394 (14) Å
b = 20.4128 (10) Å
c = 7.6711 (5) Å
β = 105.729 (6)°
V = 3171.2 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.790, T_max = 1.000
11340 measured reflections
2788 independent reflections
1497 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.212
S = 1.08
2788 reflections
204 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11A—H11Y⋯O11Aⁱ	0.84	1.77	2.614 (8)	178
O11A—H11Z⋯O11Aⁱⁱ	0.84	2.11	2.950 (14)	178
O11B—H11X⋯N3ⁱⁱⁱ	0.84	2.21	3.046 (18)	177
Symmetry codes: (i) -x+1, -y, -z+2; (ii) $[-x+1, y, -z+{\script{3\over 2}}]$ ; (iii) $[x, -y, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681203499X/lh5508sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681203499X/lh5508Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681203499X/lh5508Isup3.cml

checkCIF report

Comment top

Kresoxim-methyl is a widely used agricultural fungicide of the strobilurin group (Anke et al., 1977; Clinton et al., 2011; Balba, 2007). It is a broad-spectrum systemic compound with novel mode of action (Sudisha et al., 2005). While exploring its fate in the environment, we have derived a new compound by the process of reduction. This may contribute to the understanding of the metabolic and environmental fate of this compound. The crystal structure of the title compound (I) is presented herein.

In (I)(Fig. 1), all bond lengths and angles are normal and correspond to those observed in the related structures (Chopra et al., 2004; Kant et al., 2012a,b). The dihedral angle between the two benzene rings is 68.0 (1)°. The C—O—C—C torsion angle of the atoms joining these rings is 179.7 (2) °. The atoms of the methanol group were refined as disordered over two sets of sites with fixed occupancies of 0.86 and 0.14. The H atoms of the hydroxy group in the major component are disordered over a further two sets of sites with equal occupancies. This is a necessary arrangement to allow for hydrogen bonding without unrealistic H···H contacts. The O—H···O hydrogen bond motif of one the O—H disorder components is shown in Fig. 2. For the other disorder component in the O—H···O hydrogen bonds, the acceptors become donors and vice-versa. In the crystal, O—H···N and O—H···O hydrogen bonds connect molecules to form chains along [001].

Related literature top

The title compound was derived from kresoxim-methyl. For the biological activity of kresoxim-methyl, see: Anke et al. (1977); Clinton et al. (2011); Balba et al. (2007); Sudisha et al. (2005). For related structures, see: Chopra et al. (2004); Kant et al. (2012a,b).

Experimental top

Finely powdered sodium borohydride (6 eq., 0.06 mol) was suspended in tetrahydrofuran in presence of kresoxim-methyl (3.13 g m, 0.01 mol) under reflux (343 K) with stirring for 1 h. Then methanol (8 ml) was slowly added drop wise. Stirring and refluxing were maintained until the reaction was completed as monitored by TLC. After the end of the reaction, the reaction mixture was cooled to room temperature and quenched with a saturated solution of ammonium chloride (15 ml) for further period of 1.5 h. The product was separated by extraction with ethyl acetate (2x25 ml). The organic extracts were combined and dried over sodium sulfate and concentrated under low pressure to yield the final product. The synthesized compound was dissolved in methanol and subjected to slow evaporation to produce colourless crystals.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with ellipsoids drawn at the 40% probability level.
	Fig. 2. Part of the crystal structure showing the hydrogen bonds along [001] as dashed lines. For the other disorder component in the O—H···O hydrogen bonds, the acceptors become donors and vice-versa.

2-Methoxyimino-2-{2-[(2-methylphenoxy)methyl]phenyl}ethanol top

Crystal data top

C₁₇H₁₉NO₃	F(000) = 1216
M_r = 285.33	D_x = 1.195 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2909 reflections
a = 21.0394 (14) Å	θ = 3.6–29.0°
b = 20.4128 (10) Å	µ = 0.08 mm⁻¹
c = 7.6711 (5) Å	T = 293 K
β = 105.729 (6)°	Block, colourless
V = 3171.2 (3) Å³	0.3 × 0.2 × 0.1 mm
Z = 8

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2788 independent reflections
Radiation source: fine-focus sealed tube	1497 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
Detector resolution: 16.1049 pixels mm^-1	θ_max = 25.0°, θ_min = 3.6°
ω scans	h = −23→24
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −23→24
T_min = 0.790, T_max = 1.000	l = −9→9
11340 measured reflections

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.212	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0921P)²] where P = (F_o² + 2F_c²)/3
2788 reflections	(Δ/σ)_max = 0.002
204 parameters	Δρ_max = 0.39 e Å⁻³
2 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₇H₁₉NO₃	V = 3171.2 (3) Å³
M_r = 285.33	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 21.0394 (14) Å	µ = 0.08 mm⁻¹
b = 20.4128 (10) Å	T = 293 K
c = 7.6711 (5) Å	0.3 × 0.2 × 0.1 mm
β = 105.729 (6)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2788 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	1497 reflections with I > 2σ(I)
T_min = 0.790, T_max = 1.000	R_int = 0.052
11340 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	2 restraints
wR(F²) = 0.212	H-atom parameters constrained
S = 1.08	Δρ_max = 0.39 e Å⁻³
2788 reflections	Δρ_min = −0.22 e Å⁻³
204 parameters

Special details top

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	Occ. (<1)
O4	0.36797 (11)	0.16370 (9)	0.4565 (3)	0.0749 (7)
O13	0.24680 (10)	0.14485 (9)	0.7894 (3)	0.0689 (7)
N3	0.37326 (13)	0.10321 (12)	0.5462 (4)	0.0709 (8)
C2	0.38302 (15)	0.11036 (14)	0.7167 (4)	0.0638 (8)
C5	0.3638 (2)	0.1523 (2)	0.2722 (5)	0.1041 (13)
H5A	0.3630	0.1934	0.2110	0.156*
H5B	0.3242	0.1283	0.2174	0.156*
H5C	0.4014	0.1273	0.2629	0.156*
C6	0.39179 (15)	0.17396 (14)	0.8143 (3)	0.0544 (8)
C7	0.45455 (16)	0.19128 (17)	0.9162 (4)	0.0736 (9)
H7A	0.4898	0.1630	0.9228	0.088*
C8	0.4652 (2)	0.2500 (2)	1.0079 (5)	0.0912 (12)
H8A	0.5077	0.2616	1.0736	0.109*
C9	0.4141 (3)	0.2911 (2)	1.0029 (5)	0.0943 (12)
H9A	0.4216	0.3307	1.0653	0.113*
C10	0.3504 (2)	0.27400 (16)	0.9042 (5)	0.0785 (10)
H10A	0.3155	0.3022	0.9023	0.094*
C11	0.33831 (16)	0.21524 (14)	0.8083 (4)	0.0577 (8)
C12	0.27043 (14)	0.19845 (14)	0.7035 (4)	0.0635 (9)
H12A	0.2418	0.2361	0.6974	0.076*
H12B	0.2701	0.1864	0.5810	0.076*
C14	0.18363 (16)	0.12314 (14)	0.7087 (4)	0.0596 (8)
C15	0.16296 (18)	0.06974 (15)	0.7930 (5)	0.0722 (9)
C16	0.0989 (2)	0.04775 (18)	0.7189 (6)	0.0901 (12)
H16A	0.0832	0.0129	0.7735	0.108*
C17	0.0578 (2)	0.0762 (2)	0.5666 (7)	0.0991 (13)
H17A	0.0152	0.0604	0.5195	0.119*
C18	0.07975 (19)	0.1270 (2)	0.4858 (5)	0.0902 (12)
H18A	0.0523	0.1457	0.3820	0.108*
C19	0.14248 (17)	0.15098 (15)	0.5562 (5)	0.0737 (9)
H19A	0.1572	0.1862	0.5006	0.088*
C20	0.2088 (2)	0.03868 (18)	0.9558 (5)	0.1147 (15)
H20A	0.2484	0.0250	0.9269	0.172*
H20B	0.1877	0.0013	0.9919	0.172*
H20C	0.2197	0.0698	1.0532	0.172*
O11A	0.4567 (3)	0.0312 (2)	0.8725 (8)	0.253 (3)	0.86
H11Y	0.4837	0.0106	0.9553	0.380*	0.86
H11Z	0.4806	0.0312	0.8007	0.380*	0.86
C11A	0.3946 (2)	0.0467 (2)	0.8269 (7)	0.0952 (17)	0.86
H11A	0.3796	0.0522	0.9351	0.114*	0.43
H11B	0.3691	0.0116	0.7556	0.114*	0.43
O11B	0.3776 (10)	−0.0022 (7)	0.757 (2)	0.107 (7)	0.14
H11X	0.3746	−0.0298	0.8361	0.161*	0.14
C11B	0.3637 (19)	0.0532 (6)	0.822 (4)	0.0952 (17)	0.14
H11C	0.3875	0.0566	0.9491	0.114*	0.14
H11D	0.3168	0.0552	0.8123	0.114*	0.14

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4	0.1028 (18)	0.0737 (14)	0.0500 (13)	−0.0026 (12)	0.0234 (11)	0.0048 (10)
O13	0.0712 (15)	0.0688 (13)	0.0615 (13)	−0.0153 (11)	0.0090 (11)	0.0183 (10)
N3	0.091 (2)	0.0592 (15)	0.0623 (18)	0.0014 (13)	0.0212 (14)	−0.0015 (13)
C2	0.080 (2)	0.0564 (18)	0.0553 (19)	−0.0021 (16)	0.0193 (15)	0.0060 (15)
C5	0.141 (4)	0.120 (3)	0.050 (2)	−0.007 (3)	0.023 (2)	−0.008 (2)
C6	0.067 (2)	0.0615 (18)	0.0362 (16)	−0.0124 (16)	0.0163 (14)	0.0013 (12)
C7	0.074 (2)	0.095 (2)	0.054 (2)	−0.0094 (19)	0.0206 (17)	−0.0034 (18)
C8	0.088 (3)	0.118 (3)	0.070 (2)	−0.043 (3)	0.026 (2)	−0.019 (2)
C9	0.128 (4)	0.081 (3)	0.083 (3)	−0.043 (3)	0.045 (3)	−0.030 (2)
C10	0.110 (3)	0.063 (2)	0.075 (2)	−0.004 (2)	0.046 (2)	−0.0010 (17)
C11	0.071 (2)	0.0549 (17)	0.0504 (17)	−0.0103 (17)	0.0220 (15)	0.0061 (13)
C12	0.073 (2)	0.0567 (18)	0.0632 (19)	−0.0037 (15)	0.0227 (16)	0.0184 (15)
C14	0.067 (2)	0.0572 (18)	0.0570 (19)	−0.0061 (16)	0.0201 (16)	−0.0041 (14)
C15	0.082 (3)	0.0623 (19)	0.078 (2)	−0.0110 (19)	0.0319 (19)	−0.0012 (17)
C16	0.094 (3)	0.073 (2)	0.115 (3)	−0.025 (2)	0.050 (3)	−0.016 (2)
C17	0.070 (3)	0.096 (3)	0.130 (4)	−0.011 (2)	0.026 (3)	−0.035 (3)
C18	0.071 (3)	0.092 (3)	0.101 (3)	0.004 (2)	0.011 (2)	−0.012 (2)
C19	0.068 (2)	0.075 (2)	0.076 (2)	0.0006 (19)	0.0161 (18)	0.0016 (17)
C20	0.145 (4)	0.092 (3)	0.110 (3)	−0.029 (2)	0.038 (3)	0.036 (2)
O11A	0.166 (5)	0.175 (4)	0.355 (9)	0.019 (4)	−0.040 (4)	0.159 (5)
C11A	0.089 (5)	0.075 (3)	0.113 (4)	0.026 (3)	0.012 (3)	0.024 (3)
O11B	0.20 (2)	0.031 (8)	0.083 (12)	0.001 (11)	0.026 (12)	−0.011 (8)
C11B	0.089 (5)	0.075 (3)	0.113 (4)	0.026 (3)	0.012 (3)	0.024 (3)

Geometric parameters (Å, º) top

O4—N3	1.403 (3)	C14—C19	1.375 (4)
O4—C5	1.412 (4)	C14—C15	1.396 (4)
O13—C14	1.378 (3)	C15—C16	1.388 (5)
O13—C12	1.434 (3)	C15—C20	1.497 (5)
N3—C2	1.277 (3)	C16—C17	1.379 (5)
C2—C6	1.485 (4)	C16—H16A	0.9300
C2—C11A	1.533 (5)	C17—C18	1.352 (5)
C2—C11B	1.535 (7)	C17—H17A	0.9300
C5—H5A	0.9600	C18—C19	1.374 (4)
C5—H5B	0.9600	C18—H18A	0.9300
C5—H5C	0.9600	C19—H19A	0.9300
C6—C7	1.386 (4)	C20—H20A	0.9600
C6—C11	1.396 (4)	C20—H20B	0.9600
C7—C8	1.378 (5)	C20—H20C	0.9600
C7—H7A	0.9300	O11A—C11A	1.298 (6)
C8—C9	1.355 (5)	O11A—H11Y	0.8400
C8—H8A	0.9300	O11A—H11Z	0.8399
C9—C10	1.394 (5)	C11A—H11A	0.9700
C9—H9A	0.9300	C11A—H11B	0.9700
C10—C11	1.394 (4)	O11B—C11B	1.300 (8)
C10—H10A	0.9300	O11B—H11X	0.8400
C11—C12	1.477 (4)	C11B—H11C	0.9700
C12—H12A	0.9700	C11B—H11D	0.9700
C12—H12B	0.9700

N3—O4—C5	108.7 (2)	C19—C14—C15	120.9 (3)
C14—O13—C12	116.8 (2)	O13—C14—C15	115.2 (3)
C2—N3—O4	111.8 (2)	C16—C15—C14	116.9 (3)
N3—C2—C6	125.5 (3)	C16—C15—C20	122.6 (3)
N3—C2—C11A	115.2 (3)	C14—C15—C20	120.4 (3)
C6—C2—C11A	118.9 (3)	C17—C16—C15	121.8 (4)
N3—C2—C11B	117.4 (12)	C17—C16—H16A	119.1
C6—C2—C11B	114.4 (9)	C15—C16—H16A	119.1
O4—C5—H5A	109.5	C18—C17—C16	119.9 (4)
O4—C5—H5B	109.5	C18—C17—H17A	120.1
H5A—C5—H5B	109.5	C16—C17—H17A	120.1
O4—C5—H5C	109.5	C17—C18—C19	120.3 (4)
H5A—C5—H5C	109.5	C17—C18—H18A	119.9
H5B—C5—H5C	109.5	C19—C18—H18A	119.9
C7—C6—C11	120.1 (3)	C18—C19—C14	120.2 (3)
C7—C6—C2	118.5 (3)	C18—C19—H19A	119.9
C11—C6—C2	121.5 (3)	C14—C19—H19A	119.9
C8—C7—C6	120.5 (3)	C15—C20—H20A	109.5
C8—C7—H7A	119.7	C15—C20—H20B	109.5
C6—C7—H7A	119.7	H20A—C20—H20B	109.5
C9—C8—C7	120.4 (4)	C15—C20—H20C	109.5
C9—C8—H8A	119.8	H20A—C20—H20C	109.5
C7—C8—H8A	119.8	H20B—C20—H20C	109.5
C8—C9—C10	119.9 (3)	C11A—O11A—H11Y	138.5
C8—C9—H9A	120.0	C11A—O11A—H11Z	124.1
C10—C9—H9A	120.0	H11Y—O11A—H11Z	95.5
C9—C10—C11	120.9 (3)	O11A—C11A—C2	110.6 (4)
C9—C10—H10A	119.6	O11A—C11A—H11A	109.5
C11—C10—H10A	119.6	C2—C11A—H11A	109.5
C10—C11—C6	118.1 (3)	O11A—C11A—H11B	109.5
C10—C11—C12	119.9 (3)	C2—C11A—H11B	109.5
C6—C11—C12	122.0 (3)	H11A—C11A—H11B	108.1
O13—C12—C11	109.4 (2)	C11B—O11B—H11X	104.0
O13—C12—H12A	109.8	O11B—C11B—C2	109.9 (12)
C11—C12—H12A	109.8	O11B—C11B—H11C	109.7
O13—C12—H12B	109.8	C2—C11B—H11C	109.7
C11—C12—H12B	109.8	O11B—C11B—H11D	109.7
H12A—C12—H12B	108.2	C2—C11B—H11D	109.7
C19—C14—O13	123.9 (3)	H11C—C11B—H11D	108.2

C5—O4—N3—C2	174.3 (3)	C10—C11—C12—O13	−110.4 (3)
O4—N3—C2—C6	−3.3 (4)	C6—C11—C12—O13	69.9 (3)
O4—N3—C2—C11A	−175.6 (3)	C12—O13—C14—C19	−1.9 (4)
O4—N3—C2—C11B	157.0 (14)	C12—O13—C14—C15	178.2 (2)
N3—C2—C6—C7	−105.8 (4)	C19—C14—C15—C16	−1.8 (5)
C11A—C2—C6—C7	66.3 (4)	O13—C14—C15—C16	178.0 (3)
C11B—C2—C6—C7	93.5 (16)	C19—C14—C15—C20	178.3 (3)
N3—C2—C6—C11	75.6 (4)	O13—C14—C15—C20	−1.8 (4)
C11A—C2—C6—C11	−112.3 (3)	C14—C15—C16—C17	1.5 (5)
C11B—C2—C6—C11	−85.1 (16)	C20—C15—C16—C17	−178.6 (4)
C11—C6—C7—C8	−1.9 (4)	C15—C16—C17—C18	−0.2 (6)
C2—C6—C7—C8	179.5 (3)	C16—C17—C18—C19	−0.9 (6)
C6—C7—C8—C9	1.5 (5)	C17—C18—C19—C14	0.5 (5)
C7—C8—C9—C10	−0.1 (5)	O13—C14—C19—C18	−179.0 (3)
C8—C9—C10—C11	−0.7 (5)	C15—C14—C19—C18	0.9 (5)
C9—C10—C11—C6	0.2 (4)	N3—C2—C11A—O11A	87.9 (5)
C9—C10—C11—C12	−179.5 (3)	C6—C2—C11A—O11A	−85.0 (5)
C7—C6—C11—C10	1.1 (4)	C11B—C2—C11A—O11A	−171 (3)
C2—C6—C11—C10	179.6 (3)	N3—C2—C11B—O11B	38 (3)
C7—C6—C11—C12	−179.2 (2)	C6—C2—C11B—O11B	−160 (2)
C2—C6—C11—C12	−0.6 (4)	C11A—C2—C11B—O11B	−53.1 (15)
C14—O13—C12—C11	179.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O11A—H11Y···O11Aⁱ	0.84	1.77	2.614 (8)	178
O11A—H11Z···O11Aⁱⁱ	0.84	2.11	2.950 (14)	178
O11B—H11X···N3ⁱⁱⁱ	0.84	2.21	3.046 (18)	177

Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+1, y, −z+3/2; (iii) x, −y, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₉NO₃
M_r	285.33
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	21.0394 (14), 20.4128 (10), 7.6711 (5)
β (°)	105.729 (6)
V (Å³)	3171.2 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.3 × 0.2 × 0.1

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.790, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11340, 2788, 1497
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.212, 1.08
No. of reflections	2788
No. of parameters	204
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.22

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O11A—H11Y···O11Aⁱ	0.84	1.77	2.614 (8)	177.6
O11A—H11Z···O11Aⁱⁱ	0.84	2.11	2.950 (14)	178.1
O11B—H11X···N3ⁱⁱⁱ	0.84	2.21	3.046 (18)	176.7

Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+1, y, −z+3/2; (iii) x, −y, z+1/2.

Acknowledgements

RK acknowledges the Department of Science & Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.

References

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