Methyl 2,2-diphenyl-2-(prop-2-yn-1-yl-oxy)acetate.

The mol-ecular structure of the title compound, C(18)H(16)O(3), exhibits a new R(2)-C(COOMe)(OCH(2)CCH) group. The C-O-C-C torsion angle is 153.3 (1)°. The dihedral angles are 79.89 (5)° between phen-yl/phenyl planes, and 73.13 (5) and 79.05 (8)° for the two COOMe/phenyl plane pairs.

Related literature

For related literature on the background of this work, see: Ferguson et al. (1995 ▶); Ohkuma et al. (2000 ▶). For related structures, see: Narayanan et al. (2011 ▶); Shah et al. (2011 ▶); Siddaraju et al. (2010 ▶); Zhang et al. (2008 ▶); Zhang et al. (2011 ▶).

Experimental

Crystal data

C18H16O3

M = 280.31

Monoclinic,

a = 12.6771 (17) Å

b = 9.2410 (13) Å

c = 12.7055 (18) Å

β = 93.090 (3)°

V = 1486.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 130 K

0.37 × 0.22 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.969, T max = 0.992

13808 measured reflections

3545 independent reflections

2623 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.117

S = 1.02

3545 reflections

195 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812007982/nc2267sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007982/nc2267Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007982/nc2267Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H16O3	F(000) = 592
Mr = 280.31	Dx = 1.253 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1710 reflections
a = 12.6771 (17) Å	θ = 2.7–23.4°
b = 9.2410 (13) Å	µ = 0.09 mm−1
c = 12.7055 (18) Å	T = 130 K
β = 93.090 (3)°	Prism, colourless
V = 1486.3 (4) Å3	0.37 × 0.22 × 0.10 mm
Z = 4

Bruker SMART APEX diffractometer	3545 independent reflections
Radiation source: sealed tube	2623 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
φ and ω scans	θmax = 27.9°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −14→16
Tmin = 0.969, Tmax = 0.992	k = −12→12
13808 measured reflections	l = −16→16

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)] = 0.048	Hydrogen site location: difference Fourier map
wR(F2) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0487P)2 + 0.3727P] where P = (Fo2 + 2Fc2)/3
3545 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.19 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	Uiso*/Ueq
O1	0.79582 (9)	0.45794 (12)	0.41949 (10)	0.0378 (3)
O2	0.66203 (9)	0.37609 (11)	0.51072 (9)	0.0296 (3)
O3	0.78724 (8)	0.22289 (11)	0.28970 (8)	0.0247 (3)
C1	0.72467 (12)	0.21809 (15)	0.38023 (11)	0.0203 (3)
C2	0.73393 (12)	0.36505 (15)	0.43855 (12)	0.0233 (3)
C3	0.66088 (16)	0.51182 (17)	0.56825 (15)	0.0393 (5)
H3A	0.7287	0.5250	0.6078	0.059*
H3B	0.6038	0.5100	0.6173	0.059*
H3C	0.6494	0.5920	0.5185	0.059*
C4	0.90005 (12)	0.22196 (19)	0.31004 (13)	0.0299 (4)
H4A	0.9188	0.1639	0.3738	0.036*
H4B	0.9261	0.3219	0.3222	0.036*
C5	0.94840 (13)	0.15941 (18)	0.21894 (14)	0.0302 (4)
C6	0.99076 (16)	0.1114 (2)	0.14631 (16)	0.0432 (5)
H6	1.0260 (19)	0.068 (3)	0.0870 (19)	0.073 (7)*
C11	0.60998 (11)	0.20274 (15)	0.33670 (11)	0.0199 (3)
C12	0.57858 (12)	0.25763 (17)	0.23856 (13)	0.0271 (4)
H12A	0.6288	0.3037	0.1969	0.032*
C13	0.47418 (13)	0.24566 (19)	0.20079 (13)	0.0326 (4)
H13A	0.4534	0.2830	0.1332	0.039*
C14	0.40033 (13)	0.17983 (17)	0.26091 (13)	0.0291 (4)
H14A	0.3292	0.1700	0.2343	0.035*
C15	0.43066 (12)	0.12818 (17)	0.36029 (13)	0.0279 (4)
H15A	0.3798	0.0853	0.4028	0.033*
C16	0.53494 (12)	0.13889 (16)	0.39776 (13)	0.0247 (3)
H16A	0.5554	0.1023	0.4657	0.030*
C21	0.76008 (11)	0.09067 (15)	0.45070 (11)	0.0198 (3)
C22	0.76063 (12)	−0.04599 (16)	0.40361 (13)	0.0255 (3)
H22A	0.7343	−0.0573	0.3327	0.031*
C23	0.79918 (13)	−0.16498 (17)	0.45948 (14)	0.0307 (4)
H23A	0.7992	−0.2575	0.4269	0.037*
C24	0.83784 (13)	−0.14904 (17)	0.56317 (14)	0.0312 (4)
H24A	0.8648	−0.2305	0.6015	0.037*
C25	0.83705 (13)	−0.01480 (18)	0.61038 (13)	0.0294 (4)
H25A	0.8628	−0.0040	0.6815	0.035*
C26	0.79855 (12)	0.10528 (16)	0.55403 (12)	0.0239 (3)
H26A	0.7988	0.1977	0.5868	0.029*

	U11	U22	U33	U12	U13	U23
O1	0.0357 (7)	0.0252 (6)	0.0539 (8)	−0.0100 (5)	0.0158 (6)	−0.0027 (5)
O2	0.0363 (7)	0.0233 (6)	0.0304 (6)	−0.0054 (5)	0.0122 (5)	−0.0064 (4)
O3	0.0162 (5)	0.0372 (6)	0.0210 (6)	0.0001 (4)	0.0048 (4)	0.0035 (4)
C1	0.0200 (8)	0.0221 (7)	0.0192 (7)	−0.0014 (6)	0.0044 (6)	0.0010 (6)
C2	0.0222 (8)	0.0225 (7)	0.0252 (8)	−0.0003 (6)	0.0006 (6)	0.0029 (6)
C3	0.0522 (12)	0.0246 (8)	0.0424 (11)	−0.0033 (8)	0.0146 (9)	−0.0111 (7)
C4	0.0174 (8)	0.0434 (10)	0.0292 (9)	−0.0015 (7)	0.0042 (7)	0.0028 (7)
C5	0.0207 (8)	0.0364 (9)	0.0338 (9)	0.0061 (7)	0.0034 (7)	0.0106 (7)
C6	0.0339 (11)	0.0559 (12)	0.0407 (11)	0.0179 (9)	0.0090 (9)	0.0058 (9)
C11	0.0183 (8)	0.0195 (7)	0.0222 (8)	0.0014 (5)	0.0029 (6)	−0.0005 (5)
C12	0.0207 (8)	0.0349 (8)	0.0259 (8)	−0.0001 (6)	0.0036 (7)	0.0052 (7)
C13	0.0283 (9)	0.0455 (10)	0.0237 (8)	0.0029 (7)	−0.0016 (7)	0.0074 (7)
C14	0.0191 (8)	0.0317 (8)	0.0361 (9)	0.0006 (6)	−0.0028 (7)	0.0011 (7)
C15	0.0195 (8)	0.0289 (8)	0.0355 (9)	−0.0009 (6)	0.0042 (7)	0.0077 (7)
C16	0.0211 (8)	0.0271 (8)	0.0261 (8)	0.0005 (6)	0.0026 (6)	0.0065 (6)
C21	0.0143 (7)	0.0222 (7)	0.0231 (8)	−0.0017 (5)	0.0022 (6)	0.0003 (6)
C22	0.0241 (8)	0.0262 (8)	0.0260 (8)	0.0000 (6)	−0.0011 (7)	−0.0031 (6)
C23	0.0254 (9)	0.0236 (8)	0.0430 (10)	0.0013 (6)	0.0001 (8)	−0.0024 (7)
C24	0.0214 (8)	0.0296 (8)	0.0418 (10)	0.0013 (6)	−0.0044 (7)	0.0100 (7)
C25	0.0231 (9)	0.0364 (9)	0.0277 (9)	−0.0020 (7)	−0.0068 (7)	0.0050 (7)
C26	0.0194 (8)	0.0263 (7)	0.0260 (8)	−0.0031 (6)	−0.0001 (6)	−0.0008 (6)

O1—C2	1.1965 (18)	C12—H12A	0.9500
O2—C2	1.3312 (18)	C13—C14	1.381 (2)
O2—C3	1.4522 (18)	C13—H13A	0.9500
O3—C1	1.4327 (17)	C14—C15	1.385 (2)
O3—C4	1.4396 (18)	C14—H14A	0.9500
C1—C21	1.532 (2)	C15—C16	1.384 (2)
C1—C11	1.534 (2)	C15—H15A	0.9500
C1—C2	1.548 (2)	C16—H16A	0.9500
C3—H3A	0.9800	C21—C26	1.382 (2)
C3—H3B	0.9800	C21—C22	1.398 (2)
C3—H3C	0.9800	C22—C23	1.384 (2)
C4—C5	1.458 (2)	C22—H22A	0.9500
C4—H4A	0.9900	C23—C24	1.388 (2)
C4—H4B	0.9900	C23—H23A	0.9500
C5—C6	1.179 (3)	C24—C25	1.378 (2)
C6—H6	0.98 (2)	C24—H24A	0.9500
C11—C12	1.385 (2)	C25—C26	1.394 (2)
C11—C16	1.391 (2)	C25—H25A	0.9500
C12—C13	1.388 (2)	C26—H26A	0.9500
C2—O2—C3	116.02 (12)	C14—C13—C12	120.41 (15)
C1—O3—C4	116.32 (11)	C14—C13—H13A	119.8
O3—C1—C21	109.60 (11)	C12—C13—H13A	119.8
O3—C1—C11	105.57 (11)	C13—C14—C15	119.54 (15)
C21—C1—C11	112.45 (11)	C13—C14—H14A	120.2
O3—C1—C2	109.03 (11)	C15—C14—H14A	120.2
C21—C1—C2	112.47 (12)	C16—C15—C14	120.13 (15)
C11—C1—C2	107.43 (11)	C16—C15—H15A	119.9
O1—C2—O2	124.42 (14)	C14—C15—H15A	119.9
O1—C2—C1	124.47 (14)	C15—C16—C11	120.51 (14)
O2—C2—C1	111.08 (12)	C15—C16—H16A	119.7
O2—C3—H3A	109.5	C11—C16—H16A	119.7
O2—C3—H3B	109.5	C26—C21—C22	119.02 (13)
H3A—C3—H3B	109.5	C26—C21—C1	123.87 (13)
O2—C3—H3C	109.5	C22—C21—C1	116.90 (13)
H3A—C3—H3C	109.5	C23—C22—C21	120.55 (15)
H3B—C3—H3C	109.5	C23—C22—H22A	119.7
O3—C4—C5	108.41 (13)	C21—C22—H22A	119.7
O3—C4—H4A	110.0	C22—C23—C24	119.95 (15)
C5—C4—H4A	110.0	C22—C23—H23A	120.0
O3—C4—H4B	110.0	C24—C23—H23A	120.0
C5—C4—H4B	110.0	C25—C24—C23	119.87 (15)
H4A—C4—H4B	108.4	C25—C24—H24A	120.1
C6—C5—C4	177.6 (2)	C23—C24—H24A	120.1
C5—C6—H6	178.2 (14)	C24—C25—C26	120.22 (15)
C12—C11—C16	119.06 (14)	C24—C25—H25A	119.9
C12—C11—C1	120.77 (13)	C26—C25—H25A	119.9
C16—C11—C1	120.11 (13)	C21—C26—C25	120.38 (14)
C11—C12—C13	120.32 (15)	C21—C26—H26A	119.8
C11—C12—H12A	119.8	C25—C26—H26A	119.8
C13—C12—H12A	119.8
C4—O3—C1—C21	−52.38 (16)	C11—C12—C13—C14	0.4 (3)
C4—O3—C1—C11	−173.72 (12)	C12—C13—C14—C15	1.3 (3)
C4—O3—C1—C2	71.12 (15)	C13—C14—C15—C16	−1.8 (2)
C3—O2—C2—O1	0.2 (2)	C14—C15—C16—C11	0.7 (2)
C3—O2—C2—C1	−178.05 (13)	C12—C11—C16—C15	1.1 (2)
O3—C1—C2—O1	−10.3 (2)	C1—C11—C16—C15	178.21 (13)
C21—C1—C2—O1	111.46 (17)	O3—C1—C21—C26	119.93 (15)
C11—C1—C2—O1	−124.27 (16)	C11—C1—C21—C26	−122.97 (15)
O3—C1—C2—O2	167.95 (11)	C2—C1—C21—C26	−1.5 (2)
C21—C1—C2—O2	−70.27 (16)	O3—C1—C21—C22	−54.88 (16)
C11—C1—C2—O2	54.00 (15)	C11—C1—C21—C22	62.22 (17)
C1—O3—C4—C5	153.28 (13)	C2—C1—C21—C22	−176.34 (13)
O3—C1—C11—C12	−28.55 (17)	C26—C21—C22—C23	−0.1 (2)
C21—C1—C11—C12	−148.02 (14)	C1—C21—C22—C23	175.02 (14)
C2—C1—C11—C12	87.70 (16)	C21—C22—C23—C24	−0.1 (2)
O3—C1—C11—C16	154.35 (13)	C22—C23—C24—C25	0.4 (2)
C21—C1—C11—C16	34.87 (18)	C23—C24—C25—C26	−0.6 (2)
C2—C1—C11—C16	−89.40 (15)	C22—C21—C26—C25	−0.2 (2)
C16—C11—C12—C13	−1.6 (2)	C1—C21—C26—C25	−174.87 (14)
C1—C11—C12—C13	−178.74 (14)	C24—C25—C26—C21	0.5 (2)