2-Biphenylol revisited

The substantially disordered structure of 2-biphenylol [Perrin et al. (1987). Acta Cryst. C43, 980–982; Kapon & Reisner (1988). Acta Cryst. C44, 2039] has been reinvestigated as a function of temperature. The structure was determined at 305, 294, 145 and 90 K; crystals were taken to the lowest temperature both rapidly and slowly (0.1 K min⁻¹). The results of the previous room-temperature study were confirmed and no important structural change was found down to 90 K. Comparisons with structures known for other simple 2- and 2,2′-substituted biphenyl derivatives suggest that the molecular stacks found for 2-biphenylol are probable for related molecules. The disorder in 2-biphenylol allows the formation of some O—H...O bonds, but packing efficiency is a more important factor in this structure than is hydrogen bonding.

Computing details

For all compounds, data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in Siemens SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELX97-2 (Sheldrick, 1997) and local procedures.

Figures

(k03123)

Crystal data

C12H10O	Dx = 1.246 Mg m^−3
Mr = 170.20	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Fdd2	Cell parameters from 605 reflections
a = 12.871 (3) Å	θ = 1.0–27.5°
b = 23.939 (5) Å	µ = 0.08 mm^−1
c = 5.8870 (12) Å	T = 305 K
V = 1813.9 (6) Å^3	Rod, colourless
Z = 8	0.40 × 0.30 × 0.20 mm
F(000) = 720

Data collection

Nonius KappaCCD diffractometer	1005 independent reflections
Radiation source: fine-focus sealed tube	557 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
Detector resolution: 18 pixels mm^-1	θmax = 27.5°, θmin = 3.4°
ω scans at fixed χ = 55°	h = −16→16
Absorption correction: multi-scan SCALEPACK (Otwinowski & Minor, 1997)	k = −29→30
Tmin = 0.970, Tmax = 0.985	l = −7→7
1005 measured reflections

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)] = 0.045	w = 1/[σ^2(Fo^2) + (0.074P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.133	(Δ/σ)max = 0.001
S = 0.96	Δρmax = 0.12 e Å^−3
1005 reflections	Δρmin = −0.12 e Å^−3
90 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
57 restraints	Extinction coefficient: 0.011 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map	Absolute structure parameter: 4 (4)

Special details

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.

The absolute structure of this crystal cannot be determined from the X-ray data because it is an all light atom structure done with Mo Kα X-rays.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.0477 (9)	0.0182 (6)	0.5298 (14)	0.0546 (7)	0.797 (9)
C2	0.0660 (10)	0.0566 (4)	0.7045 (9)	0.0628 (17)	0.797 (9)
C3	0.1531 (10)	0.0900 (4)	0.7001 (11)	0.0750 (17)	0.797 (9)
H3	0.1649	0.1151	0.8177	0.090*	0.797 (9)
C4	0.2226 (11)	0.0866 (7)	0.524 (2)	0.0799 (15)	0.797 (9)
H4	0.2805	0.1098	0.5220	0.096*	0.797 (9)
C5	0.2066 (6)	0.0489 (3)	0.3519 (14)	0.0738 (16)	0.797 (9)
H5	0.2546	0.0459	0.2345	0.089*	0.797 (9)
C6	0.1190 (7)	0.0155 (4)	0.3531 (12)	0.0631 (16)	0.797 (9)
H6	0.1077	−0.0093	0.2337	0.076*	0.797 (9)
O2	−0.0045 (3)	0.06093 (17)	0.8734 (8)	0.0760 (16)	0.398 (4)
H2	−0.0021	0.0924	0.9278	0.091*	0.398 (4)
C1'	0.042 (4)	0.017 (2)	0.544 (8)	0.0546 (7)	0.203 (9)
C2'	0.107 (3)	0.0217 (19)	0.356 (8)	0.0631 (16)	0.203 (9)
C3'	0.192 (3)	0.0570 (15)	0.361 (8)	0.0738 (16)	0.203 (9)
H3'	0.2351	0.0599	0.2337	0.089*	0.203 (9)
C4'	0.215 (4)	0.088 (3)	0.552 (9)	0.0799 (15)	0.203 (9)
H4'	0.2726	0.1108	0.5546	0.096*	0.203 (9)
C5'	0.151 (4)	0.084 (2)	0.738 (7)	0.0750 (17)	0.203 (9)
H5'	0.1650	0.1057	0.8666	0.090*	0.203 (9)
C6'	0.066 (4)	0.049 (2)	0.736 (7)	0.0628 (17)	0.203 (9)
H6'	0.0238	0.0465	0.8644	0.075*	0.203 (9)
O2'	0.1016 (11)	−0.0178 (6)	0.191 (3)	0.058 (5)*	0.102 (4)
H2'	0.1229	−0.0477	0.2419	0.088*	0.102 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0522 (17)	0.0529 (13)	0.059 (2)	0.0057 (11)	−0.0034 (12)	0.0033 (14)
C2	0.0651 (14)	0.061 (3)	0.062 (3)	−0.001 (2)	−0.003 (2)	0.006 (3)
C3	0.0809 (18)	0.066 (3)	0.078 (3)	−0.0074 (19)	−0.015 (3)	0.003 (3)
C4	0.063 (3)	0.0765 (19)	0.100 (4)	−0.010 (2)	−0.006 (2)	0.009 (2)
C5	0.056 (3)	0.076 (3)	0.0887 (19)	0.006 (3)	0.010 (2)	0.007 (2)
C6	0.052 (3)	0.068 (3)	0.0689 (15)	0.008 (3)	0.0041 (17)	−0.0031 (15)
O2	0.093 (3)	0.069 (3)	0.065 (2)	−0.007 (2)	0.009 (3)	−0.010 (2)
C1'	0.0522 (17)	0.0529 (13)	0.059 (2)	0.0057 (11)	−0.0034 (12)	0.0033 (14)
C2'	0.052 (3)	0.068 (3)	0.0689 (15)	0.008 (3)	0.0041 (17)	−0.0031 (15)
C3'	0.056 (3)	0.076 (3)	0.0887 (19)	0.006 (3)	0.010 (2)	0.007 (2)
C4'	0.063 (3)	0.0765 (19)	0.100 (4)	−0.010 (2)	−0.006 (2)	0.009 (2)
C5'	0.0809 (18)	0.066 (3)	0.078 (3)	−0.0074 (19)	−0.015 (3)	0.003 (3)
C6'	0.0651 (14)	0.061 (3)	0.062 (3)	−0.001 (2)	−0.003 (2)	0.006 (3)

Geometric parameters (Å, º)

C1—C6	1.389 (6)	C1'—C1'^i	1.37 (6)
C1—C2	1.399 (6)	C1'—C2'	1.387 (17)
C1—C1^i	1.507 (15)	C1'—C6'	1.396 (17)
C2—O2	1.351 (9)	C2'—O2'	1.357 (18)
C2—C3	1.377 (6)	C2'—C3'	1.391 (16)
C3—C4	1.369 (7)	C3'—C4'	1.372 (16)
C3—H3	0.9300	C3'—H3'	0.9300
C4—C5	1.374 (6)	C4'—C5'	1.374 (16)
C4—H4	0.9300	C4'—H4'	0.9300
C5—C6	1.383 (6)	C5'—C6'	1.381 (16)
C5—H5	0.9300	C5'—H5'	0.9300
C6—H6	0.9300	C6'—H6'	0.9300
O2—H2	0.8200	O2'—H2'	0.8200
C6—C1—C2	118.1 (3)	C1'^i—C1'—C6'	120 (2)
C6—C1—C1^i	120.8 (8)	C2'—C1'—C6'	118.4 (10)
C2—C1—C1^i	121.2 (8)	O2'—C2'—C1'	119.3 (18)
O2—C2—C3	121.1 (7)	O2'—C2'—C3'	118.4 (19)
O2—C2—C1	118.6 (7)	C1'—C2'—C3'	120.3 (11)
C3—C2—C1	120.3 (4)	C4'—C3'—C2'	120.4 (12)
C4—C3—C2	120.7 (4)	C4'—C3'—H3'	119.8
C4—C3—H3	119.6	C2'—C3'—H3'	119.8
C2—C3—H3	119.6	C3'—C4'—C5'	120.0 (10)
C3—C4—C5	120.0 (3)	C3'—C4'—H4'	120.0
C3—C4—H4	120.0	C5'—C4'—H4'	120.0
C5—C4—H4	120.0	C4'—C5'—C6'	120.1 (12)
C4—C5—C6	119.9 (4)	C4'—C5'—H5'	119.9
C4—C5—H5	120.0	C6'—C5'—H5'	119.9
C6—C5—H5	120.0	C5'—C6'—C1'	120.8 (13)
C5—C6—C1	121.0 (4)	C5'—C6'—H6'	119.6
C5—C6—H6	119.5	C1'—C6'—H6'	119.6
C1—C6—H6	119.5	C2'—O2'—H2'	109.5
C1'^i—C1'—C2'	121 (2)
C6—C1—C2—O2	177.9 (10)	C1'^i—C1'—C2'—O2'	−16 (7)
C1^i—C1—C2—O2	−0.8 (18)	C6'—C1'—C2'—O2'	164 (5)
C6—C1—C2—C3	−0.6 (10)	C1'^i—C1'—C2'—C3'	−179 (9)
C1^i—C1—C2—C3	−179.2 (18)	C6'—C1'—C2'—C3'	0 (2)
O2—C2—C3—C4	−177.9 (12)	O2'—C2'—C3'—C4'	−164 (6)
C1—C2—C3—C4	0.5 (13)	C1'—C2'—C3'—C4'	0 (3)
C2—C3—C4—C5	−1.1 (17)	C2'—C3'—C4'—C5'	−1 (6)
C3—C4—C5—C6	1.6 (15)	C3'—C4'—C5'—C6'	1 (7)
C4—C5—C6—C1	−1.7 (8)	C4'—C5'—C6'—C1'	−1 (6)
C2—C1—C6—C5	1.2 (7)	C1'^i—C1'—C6'—C5'	180 (8)
C1^i—C1—C6—C5	179.8 (19)	C2'—C1'—C6'—C5'	1 (4)

Symmetry code: (i) −x, −y, z.

(k00210)

Crystal data

C12H10O	Dx = 1.246 Mg m^−3
Mr = 170.20	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Fdd2	Cell parameters from 5983 reflections
a = 12.874 (2) Å	θ = 1.0–27.5°
b = 23.940 (3) Å	µ = 0.08 mm^−1
c = 5.888 (1) Å	T = 294 K
V = 1814.7 (5) Å^3	Rod, colourless
Z = 8	0.25 × 0.10 × 0.08 mm
F(000) = 720

Data collection

Nonius KappaCCD diffractometer	1018 independent reflections
Radiation source: fine-focus sealed tube	889 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 18 pixels mm^-1	θmax = 27.5°, θmin = 3.4°
ω scans at fixed χ = 55°	h = −16→16
Absorption correction: multi-scan SCALEPACK (Otwinowski & Minor, 1997)	k = −30→29
Tmin = 0.981, Tmax = 0.994	l = −7→7
1018 measured reflections

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)] = 0.033	w = 1/[σ^2(Fo^2) + (0.0417P)^2 + 0.2808P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.081	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.07 e Å^−3
1018 reflections	Δρmin = −0.08 e Å^−3
90 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
57 restraints	Extinction coefficient: 0.0145 (17)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0 (3)

Special details

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.

The absolute structure of this crystal cannot be determined from the X-ray data because it is an all light atom structure done with Mo Kα X-rays.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.0472 (4)	0.0176 (3)	0.5304 (6)	0.0434 (8)	0.775 (5)
C2	0.0666 (4)	0.0551 (2)	0.7072 (5)	0.0525 (9)	0.775 (5)
C3	0.1539 (6)	0.0886 (3)	0.7051 (9)	0.0666 (9)	0.775 (5)
H3	0.1666	0.1126	0.8261	0.080*	0.775 (5)
C4	0.2215 (5)	0.0869 (3)	0.5266 (6)	0.0676 (11)	0.775 (5)
H4	0.2797	0.1099	0.5256	0.081*	0.775 (5)
C5	0.2035 (3)	0.0512 (2)	0.3489 (4)	0.0630 (8)	0.775 (5)
H5	0.2497	0.0499	0.2276	0.076*	0.775 (5)
C6	0.1172 (4)	0.01701 (17)	0.3492 (4)	0.0514 (8)	0.775 (5)
H6	0.1054	−0.0068	0.2270	0.062*	0.775 (5)
O2	−0.00629 (19)	0.06154 (10)	0.8794 (5)	0.0672 (9)	0.387 (3)
H2	0.0165	0.0830	0.9759	0.081*	0.387 (3)
C1'	0.0449 (14)	0.0200 (9)	0.574 (4)	0.0434 (8)	0.225 (5)
C2'	0.1167 (14)	0.0155 (7)	0.403 (3)	0.0514 (8)	0.225 (5)
C3'	0.2069 (13)	0.0483 (8)	0.406 (3)	0.0630 (8)	0.225 (5)
H3'	0.2568	0.0445	0.2931	0.076*	0.225 (5)
C4'	0.2203 (18)	0.0861 (10)	0.580 (4)	0.0676 (11)	0.225 (5)
H4'	0.2791	0.1087	0.5815	0.081*	0.225 (5)
C5'	0.149 (2)	0.0910 (12)	0.748 (5)	0.0666 (9)	0.225 (5)
H5'	0.1574	0.1186	0.8584	0.080*	0.225 (5)
C6'	0.0636 (16)	0.0546 (10)	0.758 (4)	0.0525 (9)	0.225 (5)
H6'	0.0207	0.0537	0.8854	0.063*	0.225 (5)
O2'	0.1026 (8)	−0.0179 (4)	0.207 (2)	0.074 (3)*	0.113 (3)
H2'	0.0987	0.0023	0.0952	0.111*	0.113 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0457 (6)	0.0438 (8)	0.041 (2)	0.0052 (5)	−0.0017 (12)	0.0005 (12)
C2	0.0605 (8)	0.0548 (7)	0.042 (3)	0.0013 (6)	−0.0017 (14)	−0.0005 (17)
C3	0.0723 (12)	0.0610 (10)	0.066 (3)	−0.0097 (9)	−0.0115 (18)	−0.0062 (16)
C4	0.0574 (8)	0.0674 (9)	0.078 (3)	−0.0133 (7)	−0.0100 (16)	0.0111 (19)
C5	0.0503 (7)	0.0748 (11)	0.064 (2)	−0.0003 (7)	0.0065 (14)	0.0135 (15)
C6	0.0516 (7)	0.0609 (8)	0.042 (2)	0.0035 (5)	0.0020 (13)	−0.0002 (12)
O2	0.0823 (19)	0.0671 (15)	0.0521 (14)	−0.0096 (11)	0.0058 (13)	−0.0134 (12)
C1'	0.0457 (6)	0.0438 (8)	0.041 (2)	0.0052 (5)	−0.0017 (12)	0.0005 (12)
C2'	0.0516 (7)	0.0609 (8)	0.042 (2)	0.0035 (5)	0.0020 (13)	−0.0002 (12)
C3'	0.0503 (7)	0.0748 (11)	0.064 (2)	−0.0003 (7)	0.0065 (14)	0.0135 (15)
C4'	0.0574 (8)	0.0674 (9)	0.078 (3)	−0.0133 (7)	−0.0100 (16)	0.0111 (19)
C5'	0.0723 (12)	0.0610 (10)	0.066 (3)	−0.0097 (9)	−0.0115 (18)	−0.0062 (16)
C6'	0.0605 (8)	0.0548 (7)	0.042 (3)	0.0013 (6)	−0.0017 (14)	−0.0005 (17)

Geometric parameters (Å, º)

C1—C6	1.396 (3)	C1'—C2'	1.369 (13)
C1—C2	1.397 (4)	C1'—C6'	1.387 (14)
C1—C1^i	1.480 (8)	C1'—C1'^i	1.50 (3)
C2—C3	1.380 (5)	C2'—C3'	1.402 (14)
C2—O2	1.390 (5)	C2'—O2'	1.415 (13)
C3—C4	1.365 (4)	C3'—C4'	1.378 (14)
C3—H3	0.9300	C3'—H3'	0.9300
C4—C5	1.371 (4)	C4'—C5'	1.353 (15)
C4—H4	0.9300	C4'—H4'	0.9300
C5—C6	1.380 (4)	C5'—C6'	1.409 (15)
C5—H5	0.9300	C5'—H5'	0.9300
C6—H6	0.9300	C6'—H6'	0.9300
O2—H2	0.8200	O2'—H2'	0.8200
C6—C1—C2	117.5 (2)	C2'—C1'—C1'^i	118.0 (15)
C6—C1—C1^i	121.6 (3)	C6'—C1'—C1'^i	120.9 (12)
C2—C1—C1^i	120.9 (4)	C1'—C2'—C3'	120.4 (9)
C3—C2—O2	119.4 (3)	C1'—C2'—O2'	123.8 (12)
C3—C2—C1	120.8 (3)	C3'—C2'—O2'	115.6 (11)
O2—C2—C1	119.6 (4)	C4'—C3'—C2'	118.8 (10)
C4—C3—C2	120.6 (3)	C4'—C3'—H3'	120.6
C4—C3—H3	119.7	C2'—C3'—H3'	120.6
C2—C3—H3	119.7	C5'—C4'—C3'	121.1 (9)
C3—C4—C5	119.9 (3)	C5'—C4'—H4'	119.4
C3—C4—H4	120.0	C3'—C4'—H4'	119.4
C5—C4—H4	120.0	C4'—C5'—C6'	120.4 (11)
C4—C5—C6	120.3 (3)	C4'—C5'—H5'	119.8
C4—C5—H5	119.9	C6'—C5'—H5'	119.8
C6—C5—H5	119.9	C1'—C6'—C5'	118.2 (10)
C5—C6—C1	121.0 (2)	C1'—C6'—H6'	120.9
C5—C6—H6	119.5	C5'—C6'—H6'	120.9
C1—C6—H6	119.5	C2'—O2'—H2'	109.5
C2'—C1'—C6'	120.3 (9)
C6—C1—C2—C3	−2.2 (8)	C6'—C1'—C2'—C3'	−3.9 (18)
C1^i—C1—C2—C3	−178.9 (7)	C1'^i—C1'—C2'—C3'	−174 (2)
C6—C1—C2—O2	173.2 (5)	C6'—C1'—C2'—O2'	−178.6 (17)
C1^i—C1—C2—O2	−3.4 (8)	C1'^i—C1'—C2'—O2'	11 (3)
O2—C2—C3—C4	−173.7 (7)	C1'—C2'—C3'—C4'	−1.9 (18)
C1—C2—C3—C4	1.8 (10)	O2'—C2'—C3'—C4'	173.2 (18)
C2—C3—C4—C5	−0.7 (11)	C2'—C3'—C4'—C5'	2 (3)
C3—C4—C5—C6	0.1 (9)	C3'—C4'—C5'—C6'	4 (4)
C4—C5—C6—C1	−0.7 (5)	C2'—C1'—C6'—C5'	10 (3)
C2—C1—C6—C5	1.7 (5)	C1'^i—C1'—C6'—C5'	180 (3)
C1^i—C1—C6—C5	178.3 (7)	C4'—C5'—C6'—C1'	−10 (4)

Symmetry code: (i) −x, −y, z.

(k00212)

Crystal data

C12H10O	Dx = 1.290 Mg m^−3
Mr = 170.20	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Fdd2	Cell parameters from 6063 reflections
a = 12.882 (1) Å	θ = 1.0–27.5°
b = 23.533 (2) Å	µ = 0.08 mm^−1
c = 5.7815 (8) Å	T = 145 K
V = 1752.7 (3) Å^3	Rod, colourless
Z = 8	0.25 × 0.10 × 0.08 mm
F(000) = 720

Data collection

Nonius KappaCCD diffractometer	969 independent reflections
Radiation source: fine-focus sealed tube	935 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 18 pixels mm^-1	θmax = 27.5°, θmin = 3.5°
ω scans at fixed χ = 55°	h = −16→16
Absorption correction: multi-scan SCALEPACK (Otwinowski & Minor, 1997)	k = −30→29
Tmin = 0.980, Tmax = 0.994	l = −7→7
969 measured reflections

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)] = 0.027	w = 1/[σ^2(Fo^2) + (0.0266P)^2 + 0.8287P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.065	(Δ/σ)max = 0.003
S = 1.12	Δρmax = 0.11 e Å^−3
969 reflections	Δρmin = −0.09 e Å^−3
90 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
57 restraints	Extinction coefficient: 0.0156 (13)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0 (2)

Special details

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.

The absolute structure of this crystal cannot be determined from the X-ray data because it is an all light atom structure done with Mo Kα X-rays.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.2025 (2)	0.23211 (14)	0.4717 (3)	0.0188 (5)	0.783 (5)
C2	0.1822 (2)	0.19431 (14)	0.2884 (2)	0.0231 (5)	0.783 (5)
C3	0.0952 (3)	0.16028 (17)	0.2898 (4)	0.0299 (6)	0.783 (5)
H3	0.0831	0.1348	0.1652	0.036*	0.783 (5)
C4	0.0248 (3)	0.16288 (16)	0.4723 (3)	0.0307 (6)	0.783 (5)
H4	−0.0356	0.1398	0.4720	0.037*	0.783 (5)
C5	0.0442 (2)	0.19975 (14)	0.6550 (3)	0.0290 (5)	0.783 (5)
H5	−0.0031	0.2017	0.7808	0.035*	0.783 (5)
C6	0.1315 (2)	0.23346 (11)	0.6549 (2)	0.0226 (5)	0.783 (5)
H6	0.1439	0.2582	0.7819	0.027*	0.783 (5)
O2	0.25714 (15)	0.18794 (8)	0.1153 (4)	0.0322 (6)	0.392 (2)
H2	0.2336	0.1670	0.0098	0.039*	0.392 (2)
C1'	0.2032 (10)	0.2300 (6)	0.419 (2)	0.0188 (5)	0.217 (5)
C2'	0.1360 (10)	0.2344 (5)	0.597 (2)	0.0226 (5)	0.217 (5)
C3'	0.0430 (9)	0.1991 (6)	0.597 (2)	0.0290 (5)	0.217 (5)
H3'	−0.0071	0.2016	0.7171	0.035*	0.217 (5)
C4'	0.0310 (12)	0.1622 (7)	0.415 (2)	0.0307 (6)	0.217 (5)
H4'	−0.0274	0.1375	0.4146	0.037*	0.217 (5)
C5'	0.0970 (13)	0.1592 (7)	0.239 (3)	0.0299 (6)	0.217 (5)
H5'	0.0847	0.1331	0.1165	0.036*	0.217 (5)
C6'	0.1869 (10)	0.1953 (6)	0.233 (2)	0.0231 (5)	0.217 (5)
H6'	0.2332	0.1950	0.1045	0.028*	0.217 (5)
O2'	0.1469 (6)	0.2687 (3)	0.7984 (16)	0.038 (2)*	0.108 (2)
H2'	0.1285	0.2501	0.9153	0.058*	0.108 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0220 (5)	0.0215 (6)	0.0129 (15)	0.0024 (4)	−0.0015 (9)	0.0007 (9)
C2	0.0297 (6)	0.0268 (5)	0.0128 (15)	0.0008 (5)	0.0018 (9)	0.0015 (10)
C3	0.0360 (7)	0.0300 (6)	0.0238 (18)	−0.0042 (5)	−0.0051 (12)	−0.0028 (11)
C4	0.0280 (7)	0.0340 (6)	0.0302 (18)	−0.0064 (5)	0.0006 (10)	0.0034 (12)
C5	0.0257 (5)	0.0379 (6)	0.0233 (14)	0.0001 (5)	0.0048 (10)	0.0053 (10)
C6	0.0257 (6)	0.0293 (6)	0.0129 (13)	0.0025 (4)	0.0043 (9)	0.0005 (8)
O2	0.0417 (12)	0.0316 (11)	0.0234 (11)	−0.0044 (8)	0.0018 (8)	−0.0050 (9)
C1'	0.0220 (5)	0.0215 (6)	0.0129 (15)	0.0024 (4)	−0.0015 (9)	0.0007 (9)
C2'	0.0257 (6)	0.0293 (6)	0.0129 (13)	0.0025 (4)	0.0043 (9)	0.0005 (8)
C3'	0.0257 (5)	0.0379 (6)	0.0233 (14)	0.0001 (5)	0.0048 (10)	0.0053 (10)
C4'	0.0280 (7)	0.0340 (6)	0.0302 (18)	−0.0064 (5)	0.0006 (10)	0.0034 (12)
C5'	0.0360 (7)	0.0300 (6)	0.0238 (18)	−0.0042 (5)	−0.0051 (12)	−0.0028 (11)
C6'	0.0297 (6)	0.0268 (5)	0.0128 (15)	0.0008 (5)	0.0018 (9)	0.0015 (10)

Geometric parameters (Å, º)

C1—C6	1.400 (2)	C1'—C2'	1.349 (10)
C1—C2	1.408 (2)	C1'—C6'	1.369 (11)
C1—C1^i	1.485 (6)	C1'—C1'^i	1.53 (2)
C2—C3	1.378 (4)	C2'—O2'	1.425 (11)
C2—O2	1.398 (3)	C2'—C3'	1.458 (13)
C3—C4	1.392 (3)	C3'—C4'	1.375 (12)
C3—H3	0.9500	C3'—H3'	0.9500
C4—C5	1.390 (3)	C4'—C5'	1.328 (12)
C4—H4	0.9500	C4'—H4'	0.9500
C5—C6	1.376 (3)	C5'—C6'	1.436 (14)
C5—H5	0.9500	C5'—H5'	0.9500
C6—H6	0.9500	C6'—H6'	0.9500
O2—H2	0.8400	O2'—H2'	0.8400
C6—C1—C2	117.6 (2)	C2'—C1'—C1'^i	117.3 (9)
C6—C1—C1^i	121.7 (2)	C6'—C1'—C1'^i	119.2 (8)
C2—C1—C1^i	120.7 (2)	C1'—C2'—O2'	127.2 (9)
C3—C2—O2	120.2 (2)	C1'—C2'—C3'	118.9 (8)
C3—C2—C1	120.93 (19)	O2'—C2'—C3'	113.8 (8)
O2—C2—C1	118.6 (2)	C4'—C3'—C2'	116.9 (8)
C2—C3—C4	120.6 (2)	C4'—C3'—H3'	121.5
C2—C3—H3	119.7	C2'—C3'—H3'	121.5
C4—C3—H3	119.7	C5'—C4'—C3'	123.2 (8)
C5—C4—C3	119.1 (2)	C5'—C4'—H4'	118.4
C5—C4—H4	120.4	C3'—C4'—H4'	118.4
C3—C4—H4	120.4	C4'—C5'—C6'	120.4 (9)
C6—C5—C4	120.45 (19)	C4'—C5'—H5'	119.8
C6—C5—H5	119.8	C6'—C5'—H5'	119.8
C4—C5—H5	119.8	C1'—C6'—C5'	117.1 (8)
C5—C6—C1	121.39 (18)	C1'—C6'—H6'	121.4
C5—C6—H6	119.3	C5'—C6'—H6'	121.4
C1—C6—H6	119.3	C2'—O2'—H2'	109.5
C2'—C1'—C6'	123.3 (8)
C6—C1—C2—C3	0.4 (4)	C6'—C1'—C2'—O2'	179.2 (12)
C1^i—C1—C2—C3	178.8 (4)	C1'^i—C1'—C2'—O2'	−6.1 (17)
C6—C1—C2—O2	−173.5 (2)	C6'—C1'—C2'—C3'	2.1 (14)
C1^i—C1—C2—O2	4.8 (5)	C1'^i—C1'—C2'—C3'	176.8 (15)
O2—C2—C3—C4	174.3 (3)	C1'—C2'—C3'—C4'	1.6 (14)
C1—C2—C3—C4	0.5 (5)	O2'—C2'—C3'—C4'	−175.9 (12)
C2—C3—C4—C5	−0.9 (6)	C2'—C3'—C4'—C5'	−3 (2)
C3—C4—C5—C6	0.3 (5)	C3'—C4'—C5'—C6'	1 (3)
C4—C5—C6—C1	0.6 (4)	C2'—C1'—C6'—C5'	−4.4 (19)
C2—C1—C6—C5	−0.9 (3)	C1'^i—C1'—C6'—C5'	−179.0 (16)
C1^i—C1—C6—C5	−179.3 (4)	C4'—C5'—C6'—C1'	3 (2)

Symmetry code: (i) −x+1/2, −y+1/2, z.

(k03121)

Crystal data

C12H10O	Dx = 1.304 Mg m^−3
Mr = 170.20	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Fdd2	Cell parameters from 587 reflections
a = 12.875 (3) Å	θ = 1.0–27.5°
b = 23.416 (5) Å	µ = 0.08 mm^−1
c = 5.7500 (12) Å	T = 90 K
V = 1733.5 (6) Å^3	Rod, colourless
Z = 8	0.40 × 0.30 × 0.20 mm
F(000) = 720

Data collection

Nonius KappaCCD diffractometer	964 independent reflections
Radiation source: fine-focus sealed tube	931 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 18 pixels mm^-1	θmax = 27.5°, θmin = 3.5°
ω scans at fixed χ = 55°	h = −16→16
Absorption correction: multi-scan SCALEPACK (Otwinowski & Minor, 1997)	k = −29→30
Tmin = 0.968, Tmax = 0.984	l = −7→7
964 measured reflections

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)] = 0.030	w = 1/[σ^2(Fo^2) + (0.0324P)^2 + 1.5151P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.074	(Δ/σ)max = 0.001
S = 1.08	Δρmax = 0.13 e Å^−3
964 reflections	Δρmin = −0.12 e Å^−3
90 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
57 restraints	Extinction coefficient: 0.0104 (14)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map	Absolute structure parameter: −1 (2)

Special details

Experimental. slow cooling from RT to 90 K at 0.1 K/min

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.

The absolute structure of this crystal cannot be determined from the X-ray data because it is an all light atom structure done with Mo Kα X-rays.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.2024 (2)	0.23209 (15)	0.4721 (3)	0.0154 (5)	0.811 (6)
C2	0.1819 (2)	0.19430 (14)	0.2871 (2)	0.0185 (5)	0.811 (6)
C3	0.0944 (3)	0.16020 (16)	0.2882 (3)	0.0233 (6)	0.811 (6)
H3	0.0823	0.1346	0.1628	0.028*	0.811 (6)
C4	0.0239 (3)	0.16294 (15)	0.4714 (3)	0.0245 (5)	0.811 (6)
H4	−0.0366	0.1398	0.4708	0.029*	0.811 (6)
C5	0.0432 (2)	0.20004 (14)	0.6556 (3)	0.0229 (5)	0.811 (6)
H5	−0.0045	0.2022	0.7814	0.027*	0.811 (6)
C6	0.1314 (2)	0.23368 (11)	0.6562 (2)	0.0182 (5)	0.811 (6)
H6	0.1441	0.2584	0.7842	0.022*	0.811 (6)
O2	0.25760 (16)	0.18801 (8)	0.1146 (4)	0.0245 (6)	0.406 (3)
H2	0.2359	0.1655	0.0118	0.029*	0.406 (3)
C1'	0.2035 (11)	0.2299 (7)	0.422 (3)	0.0154 (5)	0.189 (6)
C2'	0.1362 (11)	0.2342 (5)	0.600 (2)	0.0182 (5)	0.189 (6)
C3'	0.0428 (11)	0.1986 (7)	0.599 (2)	0.0229 (5)	0.189 (6)
H3'	−0.0072	0.2008	0.7200	0.027*	0.189 (6)
C4'	0.0310 (13)	0.1621 (8)	0.416 (3)	0.0245 (5)	0.189 (6)
H4'	−0.0281	0.1378	0.4151	0.029*	0.189 (6)
C5'	0.0972 (15)	0.1584 (8)	0.238 (3)	0.0233 (6)	0.189 (6)
H5'	0.0847	0.1321	0.1157	0.028*	0.189 (6)
C6'	0.1882 (12)	0.1946 (7)	0.233 (3)	0.0185 (5)	0.189 (6)
H6'	0.2352	0.1941	0.1054	0.022*	0.189 (6)
O2'	0.1473 (8)	0.2687 (4)	0.8009 (19)	0.033 (3)*	0.094 (3)
H2'	0.0954	0.2901	0.8139	0.049*	0.094 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0182 (5)	0.0172 (6)	0.0109 (14)	0.0018 (4)	−0.0006 (9)	0.0012 (9)
C2	0.0229 (7)	0.0222 (6)	0.0103 (15)	0.0009 (5)	0.0025 (9)	0.0004 (10)
C3	0.0281 (7)	0.0242 (6)	0.0177 (17)	−0.0028 (5)	−0.0026 (11)	−0.0025 (10)
C4	0.0227 (8)	0.0274 (6)	0.0236 (16)	−0.0044 (6)	0.0015 (10)	0.0017 (11)
C5	0.0222 (5)	0.0294 (6)	0.0170 (13)	0.0002 (5)	0.0038 (9)	0.0026 (10)
C6	0.0204 (6)	0.0238 (6)	0.0105 (13)	0.0022 (5)	0.0036 (9)	0.0000 (8)
O2	0.0323 (12)	0.0237 (11)	0.0175 (11)	−0.0041 (8)	0.0011 (8)	−0.0026 (9)
C1'	0.0182 (5)	0.0172 (6)	0.0109 (14)	0.0018 (4)	−0.0006 (9)	0.0012 (9)
C2'	0.0204 (6)	0.0238 (6)	0.0105 (13)	0.0022 (5)	0.0036 (9)	0.0000 (8)
C3'	0.0222 (5)	0.0294 (6)	0.0170 (13)	0.0002 (5)	0.0038 (9)	0.0026 (10)
C4'	0.0227 (8)	0.0274 (6)	0.0236 (16)	−0.0044 (6)	0.0015 (10)	0.0017 (11)
C5'	0.0281 (7)	0.0242 (6)	0.0177 (17)	−0.0028 (5)	−0.0026 (11)	−0.0025 (10)
C6'	0.0229 (7)	0.0222 (6)	0.0103 (15)	0.0009 (5)	0.0025 (9)	0.0004 (10)

Geometric parameters (Å, º)

C1—C6	1.399 (2)	C1'—C2'	1.346 (12)
C1—C2	1.409 (2)	C1'—C6'	1.379 (12)
C1—C1^i	1.485 (6)	C1'—C1'^i	1.52 (3)
C2—C3	1.380 (3)	C2'—O2'	1.415 (12)
C2—O2	1.399 (3)	C2'—C3'	1.464 (14)
C3—C4	1.392 (3)	C3'—C4'	1.363 (13)
C3—H3	0.9500	C3'—H3'	0.9500
C4—C5	1.392 (3)	C4'—C5'	1.334 (13)
C4—H4	0.9500	C4'—H4'	0.9500
C5—C6	1.382 (3)	C5'—C6'	1.446 (15)
C5—H5	0.9500	C5'—H5'	0.9500
C6—H6	0.9500	C6'—H6'	0.9500
O2—H2	0.8400	O2'—H2'	0.8400
C6—C1—C2	117.74 (19)	C2'—C1'—C1'^i	117.4 (11)
C6—C1—C1^i	121.6 (2)	C6'—C1'—C1'^i	118.8 (9)
C2—C1—C1^i	120.6 (2)	C1'—C2'—O2'	126.8 (10)
C3—C2—O2	120.7 (2)	C1'—C2'—C3'	118.8 (9)
C3—C2—C1	120.86 (18)	O2'—C2'—C3'	114.3 (9)
O2—C2—C1	118.1 (2)	C4'—C3'—C2'	116.9 (9)
C2—C3—C4	120.57 (19)	C4'—C3'—H3'	121.5
C2—C3—H3	119.7	C2'—C3'—H3'	121.5
C4—C3—H3	119.7	C5'—C4'—C3'	124.1 (9)
C5—C4—C3	119.25 (19)	C5'—C4'—H4'	118.0
C5—C4—H4	120.4	C3'—C4'—H4'	118.0
C3—C4—H4	120.4	C4'—C5'—C6'	119.8 (9)
C6—C5—C4	120.26 (18)	C4'—C5'—H5'	120.1
C6—C5—H5	119.9	C6'—C5'—H5'	120.1
C4—C5—H5	119.9	C1'—C6'—C5'	116.7 (9)
C5—C6—C1	121.31 (17)	C1'—C6'—H6'	121.6
C5—C6—H6	119.3	C5'—C6'—H6'	121.6
C1—C6—H6	119.3	C2'—O2'—H2'	109.5
C2'—C1'—C6'	123.6 (9)
C6—C1—C2—C3	0.1 (4)	C6'—C1'—C2'—O2'	178.9 (15)
C1^i—C1—C2—C3	178.9 (4)	C1'^i—C1'—C2'—O2'	−6 (2)
C6—C1—C2—O2	−173.4 (2)	C6'—C1'—C2'—C3'	1.8 (16)
C1^i—C1—C2—O2	5.3 (5)	C1'^i—C1'—C2'—C3'	176.6 (18)
O2—C2—C3—C4	174.1 (3)	C1'—C2'—C3'—C4'	1.1 (15)
C1—C2—C3—C4	0.8 (5)	O2'—C2'—C3'—C4'	−176.4 (14)
C2—C3—C4—C5	−0.8 (6)	C2'—C3'—C4'—C5'	−2 (3)
C3—C4—C5—C6	−0.1 (5)	C3'—C4'—C5'—C6'	0 (3)
C4—C5—C6—C1	1.0 (4)	C2'—C1'—C6'—C5'	−4 (2)
C2—C1—C6—C5	−1.0 (3)	C1'^i—C1'—C6'—C5'	−178.3 (19)
C1^i—C1—C6—C5	−179.7 (4)	C4'—C5'—C6'—C1'	3 (3)

Symmetry code: (i) −x+1/2, −y+1/2, z.