(R,R)-(+)-2-(2-Methacrylo­yloxy)-1,2-diphenyl­ethanol

The title compound, C₁₈H₁₈O₃, was synthesized with pure optically active reagents. The mol­ecules possess two chiral atoms and are linked through O—H...O hydrogen bonds in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.046
• wR factor = 0.140
• Data-to-parameter ratio = 7.9

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.115
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.87
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT362_ALERT_2_C Short  C(sp3)-C(sp2) Bond  C16    -   C17    ...       1.40 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.10
           From the CIF: _reflns_number_total               1511
           Count of symmetry unique reflns         1517
           Completeness (_total/calc)             99.60%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: XSCANS (Bruker, 1999); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1997); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXTL-Plus.

(R,R)-(+)-2-(2-Methacryloyloxy)-1,2-diphenylethanol

Crystal data

C18H18O3	F(000) = 300
Mr = 282.32	Dx = 1.222 Mg m^−3
Monoclinic, P21	Melting point = 360–362 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 12.094 (5) Å	Cell parameters from 40 reflections
b = 5.756 (3) Å	θ = 3.8–10.0°
c = 12.503 (6) Å	µ = 0.08 mm^−1
β = 118.18 (2)°	T = 298 K
V = 767.1 (6) Å^3	Needle, colourless
Z = 2	0.60 × 0.12 × 0.05 mm

Data collection

Siemens P4 diffractometer	Rint = 0.115
Radiation source: fine-focus sealed tube	θmax = 25.1°, θmin = 1.9°
Graphite monochromator	h = −14→14
θ/2θ scans	k = −6→6
6004 measured reflections	l = −14→14
1511 independent reflections	3 standard reflections every 97 reflections
907 reflections with I > 2σ(I)	intensity decay: 3.8%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.046	w = 1/[σ^2(Fo^2) + (0.0565P)^2 + 0.0836P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.140	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.16 e Å^−3
1511 reflections	Δρmin = −0.13 e Å^−3
192 parameters	Extinction correction: SHELXTL-Plus, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.034 (8)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack, 1983 (1214 Friedel pairs)
Secondary atom site location: difference Fourier map

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.5302 (2)	0.3349 (9)	0.4764 (3)	0.0903 (12)
H1A	0.5542	0.2365	0.5361	0.135*
O2	0.4227 (2)	0.3360 (6)	0.2331 (3)	0.0715 (9)
O3	0.3725 (3)	0.6872 (8)	0.2676 (3)	0.0941 (12)
C1	0.7034 (4)	0.4486 (10)	0.2203 (3)	0.0730 (14)
H1B	0.7269	0.5869	0.2640	0.088*
C2	0.7592 (5)	0.3872 (15)	0.1499 (5)	0.098 (2)
H2A	0.8200	0.4826	0.1473	0.117*
C3	0.7254 (6)	0.1899 (15)	0.0855 (5)	0.102 (2)
H3A	0.7624	0.1485	0.0378	0.122*
C4	0.6368 (5)	0.0495 (13)	0.0899 (4)	0.0946 (18)
H4A	0.6127	−0.0865	0.0444	0.113*
C5	0.5825 (4)	0.1092 (10)	0.1618 (4)	0.0769 (14)
H5A	0.5235	0.0109	0.1658	0.092*
C6	0.6150 (3)	0.3125 (9)	0.2275 (3)	0.0590 (11)
C7	0.5559 (3)	0.3818 (9)	0.3037 (3)	0.0580 (11)
H7A	0.5685	0.5489	0.3201	0.070*
C8	0.6032 (3)	0.2534 (9)	0.4229 (4)	0.0662 (13)
H8A	0.5884	0.0866	0.4067	0.079*
C9	0.7409 (4)	0.2944 (9)	0.5021 (3)	0.0597 (12)
C10	0.7830 (4)	0.4953 (10)	0.5684 (4)	0.0736 (14)
H10A	0.7255	0.6056	0.5657	0.088*
C11	0.9096 (5)	0.5351 (12)	0.6390 (4)	0.0818 (15)
H11A	0.9366	0.6729	0.6826	0.098*
C12	0.9965 (4)	0.3738 (12)	0.6458 (4)	0.0782 (15)
H12A	1.0818	0.4002	0.6947	0.094*
C13	0.9563 (4)	0.1782 (11)	0.5807 (4)	0.0756 (15)
H13A	1.0144	0.0696	0.5831	0.091*
C14	0.8290 (4)	0.1354 (9)	0.5098 (3)	0.0664 (13)
H14A	0.8030	−0.0033	0.4668	0.080*
C15	0.3419 (4)	0.4934 (12)	0.2268 (4)	0.0665 (14)
C16	0.2117 (4)	0.4072 (11)	0.1686 (4)	0.0726 (15)
C17	0.1869 (5)	0.1821 (13)	0.1195 (6)	0.112 (2)
H17A	0.2073	0.1733	0.0541	0.168*
H17B	0.0997	0.1471	0.0895	0.168*
H17C	0.2369	0.0722	0.1812	0.168*
C18	0.1213 (5)	0.5536 (15)	0.1676 (5)	0.1026 (19)
H18A	0.0381	0.5050	0.1330	0.123*
H18B	0.1432	0.7011	0.2015	0.123*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0764 (19)	0.117 (3)	0.093 (2)	0.026 (2)	0.0524 (16)	0.030 (2)
O2	0.0547 (15)	0.066 (2)	0.0864 (19)	0.0035 (19)	0.0269 (14)	−0.0042 (18)
O3	0.074 (2)	0.081 (3)	0.114 (3)	0.017 (2)	0.0335 (19)	−0.005 (3)
C1	0.079 (3)	0.074 (4)	0.068 (2)	−0.008 (3)	0.037 (2)	−0.001 (3)
C2	0.091 (3)	0.131 (7)	0.085 (3)	−0.011 (4)	0.054 (3)	0.000 (4)
C3	0.107 (4)	0.128 (7)	0.069 (3)	0.018 (5)	0.041 (3)	−0.004 (4)
C4	0.098 (4)	0.094 (5)	0.074 (3)	0.019 (4)	0.026 (3)	−0.017 (3)
C5	0.076 (3)	0.065 (4)	0.084 (3)	−0.001 (3)	0.033 (2)	−0.006 (3)
C6	0.057 (2)	0.057 (3)	0.056 (2)	0.002 (3)	0.0201 (18)	0.004 (2)
C7	0.050 (2)	0.052 (3)	0.064 (2)	−0.002 (2)	0.0207 (17)	−0.002 (2)
C8	0.065 (2)	0.062 (4)	0.082 (3)	0.006 (2)	0.043 (2)	0.007 (3)
C9	0.065 (2)	0.064 (3)	0.054 (2)	0.009 (3)	0.0311 (19)	0.003 (2)
C10	0.082 (3)	0.069 (4)	0.068 (3)	0.016 (3)	0.035 (2)	0.003 (3)
C11	0.099 (4)	0.072 (4)	0.073 (3)	−0.009 (4)	0.039 (3)	−0.009 (3)
C12	0.069 (3)	0.095 (5)	0.065 (3)	−0.004 (3)	0.027 (2)	−0.002 (3)
C13	0.061 (3)	0.095 (5)	0.067 (3)	0.013 (3)	0.027 (2)	−0.003 (3)
C14	0.072 (3)	0.062 (4)	0.061 (2)	0.007 (3)	0.027 (2)	−0.001 (2)
C15	0.055 (3)	0.080 (4)	0.058 (2)	0.006 (3)	0.022 (2)	−0.002 (3)
C16	0.056 (2)	0.101 (5)	0.056 (2)	0.001 (3)	0.0225 (19)	0.012 (3)
C17	0.075 (3)	0.123 (7)	0.119 (4)	−0.016 (4)	0.030 (3)	−0.033 (5)
C18	0.073 (3)	0.112 (5)	0.127 (4)	0.007 (4)	0.051 (3)	0.003 (5)

Geometric parameters (Å, º)

O1—C8	1.415 (5)	C8—H8A	0.9800
O1—H1A	0.8703	C9—C14	1.373 (6)
O2—C15	1.308 (6)	C9—C10	1.373 (7)
O2—C7	1.450 (4)	C10—C11	1.378 (6)
O3—C15	1.209 (7)	C10—H10A	0.9300
C1—C6	1.362 (6)	C11—C12	1.375 (7)
C1—C2	1.385 (6)	C11—H11A	0.9300
C1—H1B	0.9300	C12—C13	1.339 (8)
C2—C3	1.339 (9)	C12—H12A	0.9300
C2—H2A	0.9300	C13—C14	1.389 (6)
C3—C4	1.363 (8)	C13—H13A	0.9300
C3—H3A	0.9300	C14—H14A	0.9300
C4—C5	1.385 (7)	C15—C16	1.473 (7)
C4—H4A	0.9300	C16—C18	1.377 (8)
C5—C6	1.375 (7)	C16—C17	1.404 (8)
C5—H5A	0.9300	C17—H17A	0.9600
C6—C7	1.489 (5)	C17—H17B	0.9600
C7—C8	1.514 (5)	C17—H17C	0.9600
C7—H7A	0.9800	C18—H18A	0.9300
C8—C9	1.500 (5)	C18—H18B	0.9300
C8—O1—H1A	99.2	C14—C9—C8	121.6 (4)
C15—O2—C7	119.7 (4)	C10—C9—C8	120.7 (4)
C6—C1—C2	121.9 (5)	C9—C10—C11	120.6 (5)
C6—C1—H1B	119.1	C9—C10—H10A	119.7
C2—C1—H1B	119.1	C11—C10—H10A	119.7
C3—C2—C1	119.8 (6)	C12—C11—C10	120.9 (5)
C3—C2—H2A	120.1	C12—C11—H11A	119.6
C1—C2—H2A	120.1	C10—C11—H11A	119.6
C2—C3—C4	120.1 (6)	C13—C12—C11	118.9 (4)
C2—C3—H3A	120.0	C13—C12—H12A	120.6
C4—C3—H3A	120.0	C11—C12—H12A	120.6
C3—C4—C5	120.1 (6)	C12—C13—C14	120.8 (5)
C3—C4—H4A	119.9	C12—C13—H13A	119.6
C5—C4—H4A	119.9	C14—C13—H13A	119.6
C6—C5—C4	120.6 (5)	C9—C14—C13	121.1 (5)
C6—C5—H5A	119.7	C9—C14—H14A	119.5
C4—C5—H5A	119.7	C13—C14—H14A	119.5
C1—C6—C5	117.5 (4)	O3—C15—O2	122.8 (5)
C1—C6—C7	121.1 (4)	O3—C15—C16	124.2 (5)
C5—C6—C7	121.4 (4)	O2—C15—C16	112.9 (6)
O2—C7—C6	107.0 (3)	C18—C16—C17	123.8 (5)
O2—C7—C8	107.7 (3)	C18—C16—C15	117.2 (6)
C6—C7—C8	115.3 (3)	C17—C16—C15	119.0 (5)
O2—C7—H7A	108.9	C16—C17—H17A	109.5
C6—C7—H7A	108.9	C16—C17—H17B	109.5
C8—C7—H7A	108.9	H17A—C17—H17B	109.5
O1—C8—C9	112.4 (4)	C16—C17—H17C	109.5
O1—C8—C7	105.9 (3)	H17A—C17—H17C	109.5
C9—C8—C7	111.0 (3)	H17B—C17—H17C	109.5
O1—C8—H8A	109.1	C16—C18—H18A	120.0
C9—C8—H8A	109.1	C16—C18—H18B	120.0
C7—C8—H8A	109.1	H18A—C18—H18B	120.0
C14—C9—C10	117.7 (4)
C6—C1—C2—C3	0.7 (8)	O1—C8—C9—C14	142.5 (4)
C1—C2—C3—C4	−0.3 (9)	C7—C8—C9—C14	−99.1 (5)
C2—C3—C4—C5	−0.7 (9)	O1—C8—C9—C10	−38.4 (6)
C3—C4—C5—C6	1.5 (8)	C7—C8—C9—C10	80.0 (5)
C2—C1—C6—C5	0.0 (7)	C14—C9—C10—C11	0.6 (6)
C2—C1—C6—C7	−179.9 (4)	C8—C9—C10—C11	−178.5 (4)
C4—C5—C6—C1	−1.1 (6)	C9—C10—C11—C12	−0.8 (7)
C4—C5—C6—C7	178.9 (4)	C10—C11—C12—C13	1.2 (7)
C15—O2—C7—C6	−133.5 (4)	C11—C12—C13—C14	−1.6 (7)
C15—O2—C7—C8	101.9 (4)	C10—C9—C14—C13	−1.0 (6)
C1—C6—C7—O2	136.6 (4)	C8—C9—C14—C13	178.1 (4)
C5—C6—C7—O2	−43.4 (5)	C12—C13—C14—C9	1.5 (7)
C1—C6—C7—C8	−103.6 (5)	C7—O2—C15—O3	7.4 (6)
C5—C6—C7—C8	76.4 (5)	C7—O2—C15—C16	−170.9 (3)
O2—C7—C8—O1	−57.1 (4)	O3—C15—C16—C18	−4.0 (7)
C6—C7—C8—O1	−176.5 (4)	O2—C15—C16—C18	174.2 (4)
O2—C7—C8—C9	−179.4 (4)	O3—C15—C16—C17	177.0 (5)
C6—C7—C8—C9	61.2 (5)	O2—C15—C16—C17	−4.7 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3^i	0.87	2.20	2.965 (5)	147
O1—H1A···O1^i	0.87	2.50	3.094 (7)	126

Symmetry code: (i) −x+1, y−1/2, −z+1.