Structure and piezochromism of pyrene-1-carbaldehyde at high pressure

The crystal structure of pyrene-1-carbaldehyde (PA), a model polyaromatic hydrocarbon, highly luminescent in the solid state and crystallizing in the triclinic system, has been re-determined at several pressures ranging from atmospheric up to 3 GPa using a diamond anvil cell. A `multi-crystal' approach was used in crystal structure determination, significantly improving completeness of X-ray diffraction data attainable for such a low-symmetry system. The crystal structure consists of infinite π-stacks of PA molecules with discernible dimers, which resemble aggregates formed by pyrene derivatives in solution as well as in the solid state. A series of measurements showed that the average inter-planar distance between individual molecules within π-stacks decreases with pressure in the investigated range. This results in piezochromic properties of PA: a significant sample color change as well as a red-shift of fluorescence with pressure, as studied with UV–vis spectroscopy. Periodic DFT calculations allowed us to relate the variations in the crystal structure with pressure to the changes in the electronic structure of this material.

Computing details

Data collection: CrysAlis PRO 1.171.38.43c (Rigaku OD, 2015) for 0kbar; CrysAlis PRO, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) for 8kbar, 10kbar, 15kbar, 18kbar, 28kbar. Cell refinement: CrysAlis PRO 1.171.38.43c (Rigaku OD, 2015) for 0kbar; CrysAlis PRO, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) for 8kbar, 10kbar, 15kbar, 18kbar, 28kbar. Data reduction: CrysAlis PRO 1.171.38.43c (Rigaku OD, 2015) for 0kbar; CrysAlis PRO, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) for 8kbar, 10kbar, 15kbar, 18kbar, 28kbar. For all structures, program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

(0kbar)

Crystal data

C17H10O	Z = 2
Mr = 230.25	F(000) = 240
Triclinic, P1	Dx = 1.410 Mg m^−3
a = 6.92715 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.3336 (2) Å	Cell parameters from 16541 reflections
c = 10.4706 (2) Å	θ = 2.7–45.2°
α = 109.898 (2)°	µ = 0.09 mm^−1
β = 98.9790 (19)°	T = 279 K
γ = 100.773 (2)°	Plate, clear yellow
V = 542.32 (2) Å^3	0.36 × 0.29 × 0.11 mm

Data collection

SuperNova, Single source at offset, Eos diffractometer	9109 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	6621 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.032
Detector resolution: 16.0026 pixels mm^-1	θmax = 45.4°, θmin = 2.1°
ω scans	h = −13→13
Absorption correction: multi-scan CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −16→16
Tmin = 0.611, Tmax = 1.000	l = −20→20
54427 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.179	w = 1/[σ^2(Fo^2) + (0.0843P)^2 + 0.0851P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
9109 reflections	Δρmax = 0.89 e Å^−3
163 parameters	Δρmin = −0.36 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.20750 (9)	−0.18858 (8)	−0.19284 (6)	0.01593 (9)
C2	0.21120 (8)	−0.15559 (7)	−0.05025 (5)	0.01358 (8)
C3	0.17281 (9)	−0.29310 (7)	0.00324 (6)	0.01658 (9)
H3	0.145784	−0.410457	−0.057135	0.020*
C4	0.17538 (9)	−0.25433 (8)	0.14066 (6)	0.01776 (9)
H4	0.149992	−0.346094	0.172227	0.021*
C5	0.21607 (9)	−0.07624 (7)	0.23796 (6)	0.01599 (9)
C6	0.21344 (12)	−0.03576 (9)	0.37899 (6)	0.02297 (11)
H6	0.186201	−0.126441	0.411535	0.028*
C7	0.25114 (13)	0.13856 (10)	0.47053 (7)	0.02605 (13)
H7	0.247134	0.163741	0.563545	0.031*
C8	0.29492 (11)	0.27580 (9)	0.42368 (6)	0.02163 (11)
H8	0.321135	0.392087	0.486043	0.026*
C9	0.29994 (9)	0.24078 (7)	0.28383 (6)	0.01582 (9)
C10	0.34275 (10)	0.37971 (7)	0.23270 (6)	0.01838 (10)
H10	0.370955	0.496708	0.294089	0.022*
C11	0.34271 (9)	0.34299 (7)	0.09629 (6)	0.01787 (9)
H11	0.371688	0.435423	0.065822	0.021*
C12	0.29884 (8)	0.16433 (7)	−0.00213 (6)	0.01442 (8)
C13	0.29658 (10)	0.12659 (8)	−0.14327 (6)	0.01798 (9)
H13	0.324728	0.218108	−0.174821	0.022*
C14	0.25241 (10)	−0.04709 (8)	−0.23586 (6)	0.01872 (10)
H14	0.252569	−0.070415	−0.329245	0.022*
C15	0.25650 (7)	0.02308 (7)	0.04502 (5)	0.01246 (8)
C16	0.25829 (8)	0.06261 (7)	0.18899 (5)	0.01343 (8)
C17	0.15400 (11)	−0.36462 (9)	−0.30593 (7)	0.02265 (11)
H17	0.163874	−0.366221	−0.393899	0.027*
O1	0.09873 (11)	−0.50771 (7)	−0.29909 (6)	0.03302 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0163 (2)	0.01704 (19)	0.01302 (17)	0.00463 (15)	0.00482 (14)	0.00327 (15)
C2	0.01345 (18)	0.01298 (17)	0.01337 (17)	0.00324 (13)	0.00397 (13)	0.00364 (14)
C3	0.0182 (2)	0.01262 (17)	0.0176 (2)	0.00285 (15)	0.00443 (16)	0.00474 (15)
C4	0.0206 (2)	0.01516 (19)	0.0185 (2)	0.00326 (16)	0.00480 (17)	0.00825 (16)
C5	0.0177 (2)	0.01664 (19)	0.01431 (18)	0.00372 (15)	0.00409 (15)	0.00700 (15)
C6	0.0306 (3)	0.0247 (3)	0.0155 (2)	0.0059 (2)	0.0063 (2)	0.01019 (19)
C7	0.0362 (4)	0.0281 (3)	0.0129 (2)	0.0072 (3)	0.0065 (2)	0.0069 (2)
C8	0.0268 (3)	0.0212 (2)	0.01282 (19)	0.0061 (2)	0.00325 (18)	0.00213 (17)
C9	0.0171 (2)	0.01500 (18)	0.01311 (17)	0.00435 (15)	0.00236 (14)	0.00307 (14)
C10	0.0211 (2)	0.01318 (18)	0.0179 (2)	0.00429 (16)	0.00257 (17)	0.00331 (15)
C11	0.0207 (2)	0.01345 (18)	0.0197 (2)	0.00421 (16)	0.00421 (17)	0.00693 (16)
C12	0.01499 (18)	0.01420 (18)	0.01478 (18)	0.00391 (14)	0.00382 (14)	0.00618 (14)
C13	0.0211 (2)	0.0193 (2)	0.0161 (2)	0.00523 (17)	0.00583 (17)	0.00929 (17)
C14	0.0213 (2)	0.0222 (2)	0.01349 (18)	0.00608 (18)	0.00593 (16)	0.00686 (17)
C15	0.01257 (17)	0.01256 (16)	0.01225 (16)	0.00350 (13)	0.00336 (13)	0.00443 (13)
C16	0.01393 (18)	0.01375 (17)	0.01208 (17)	0.00368 (14)	0.00297 (13)	0.00426 (14)
C17	0.0258 (3)	0.0210 (2)	0.0161 (2)	0.0050 (2)	0.00738 (19)	0.00053 (18)
O1	0.0473 (4)	0.0184 (2)	0.0252 (2)	0.0013 (2)	0.0148 (2)	−0.00053 (17)

Geometric parameters (Å, º)

C1—C2	1.4182 (7)	C8—C9	1.3998 (8)
C1—C14	1.3994 (8)	C9—C10	1.4347 (8)
C1—C17	1.4728 (8)	C9—C16	1.4216 (7)
C2—C3	1.4377 (7)	C10—C11	1.3550 (9)
C2—C15	1.4238 (7)	C11—C12	1.4352 (8)
C3—C4	1.3596 (8)	C12—C13	1.3992 (8)
C4—C5	1.4299 (8)	C12—C15	1.4237 (7)
C5—C6	1.4023 (8)	C13—C14	1.3838 (8)
C5—C16	1.4183 (7)	C15—C16	1.4268 (7)
C6—C7	1.3890 (10)	C17—O1	1.2123 (9)
C7—C8	1.3926 (10)
C2—C1—C17	125.32 (5)	C16—C9—C10	118.90 (5)
C14—C1—C2	119.91 (5)	C11—C10—C9	120.97 (5)
C14—C1—C17	114.75 (5)	C10—C11—C12	121.33 (5)
C1—C2—C3	123.42 (5)	C13—C12—C11	121.26 (5)
C1—C2—C15	118.27 (5)	C13—C12—C15	119.51 (5)
C15—C2—C3	118.31 (5)	C15—C12—C11	119.24 (5)
C4—C3—C2	121.06 (5)	C14—C13—C12	119.92 (5)
C3—C4—C5	121.76 (5)	C13—C14—C1	121.81 (5)
C6—C5—C4	121.99 (5)	C2—C15—C16	120.26 (5)
C6—C5—C16	119.46 (5)	C12—C15—C2	120.56 (5)
C16—C5—C4	118.55 (5)	C12—C15—C16	119.18 (5)
C7—C6—C5	120.60 (6)	C5—C16—C9	119.59 (5)
C6—C7—C8	120.32 (6)	C5—C16—C15	120.03 (5)
C7—C8—C9	120.77 (6)	C9—C16—C15	120.37 (5)
C8—C9—C10	121.84 (5)	O1—C17—C1	128.33 (6)
C8—C9—C16	119.25 (5)

(8kbar)

Crystal data

C17H10O	V = 509.65 (16) Å^3
Mr = 230.25	Z = 2
Triclinic, P1	F(000) = 240
a = 6.7049 (9) Å	Dx = 1.500 Mg m^−3
b = 8.1989 (12) Å	Synchrotron radiation, λ = 0.4859 Å
c = 10.329 (2) Å	Cell parameters from 850 reflections
α = 109.691 (17)°	θ = 1.8–22.2°
β = 99.378 (15)°	µ = 0.05 mm^−1
γ = 100.628 (12)°	T = 293 K

Data collection

Dectris-CrysAlisPro-abstract goniometer imported dectris images diffractometer	2730 independent reflections
Radiation source: synchrotron	1587 reflections with I > 2σ(I)
Synchrotron monochromator	Rint = 0.163
ω scans	θmax = 22.7°, θmin = 1.5°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −10→10
Tmin = 0.275, Tmax = 1.000	k = −12→12
2730 measured reflections	l = −15→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.160	H-atom parameters constrained
wR(F^2) = 0.454	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.58	(Δ/σ)max < 0.001
2730 reflections	Δρmax = 0.92 e Å^−3
165 parameters	Δρmin = −0.83 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 3-component twin.

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

	x	y	z	Uiso*/Ueq
C15	0.2422 (7)	0.4762 (6)	0.4564 (7)	0.0178 (13)
C16	0.2369 (7)	0.4352 (6)	0.3101 (7)	0.0199 (13)
O1	0.4063 (7)	1.0152 (5)	0.8057 (5)	0.0456 (14)
C2	0.2893 (7)	0.6567 (6)	0.5522 (7)	0.0189 (12)
C12	0.2001 (7)	0.3313 (6)	0.5047 (7)	0.0191 (12)
C10	0.1523 (8)	0.1137 (7)	0.2657 (8)	0.0262 (15)
H10	0.122280	−0.004977	0.203340	0.031*
C3	0.3264 (8)	0.7960 (7)	0.4964 (8)	0.0241 (14)
H3	0.355438	0.915232	0.557311	0.029*
C13	0.2067 (8)	0.3702 (7)	0.6476 (7)	0.0240 (13)
H13	0.180832	0.277422	0.680176	0.029*
C5	0.2785 (8)	0.5775 (7)	0.2599 (7)	0.0222 (13)
C4	0.3199 (8)	0.7573 (7)	0.3587 (8)	0.0248 (15)
H4	0.343184	0.850676	0.326493	0.030*
C11	0.1548 (8)	0.1513 (6)	0.4040 (7)	0.0225 (14)
H11	0.126203	0.057093	0.434724	0.027*
C14	0.2514 (8)	0.5448 (6)	0.7404 (7)	0.0228 (12)
H14	0.253049	0.568083	0.835216	0.027*
C9	0.1956 (8)	0.2557 (7)	0.2149 (7)	0.0238 (14)
C6	0.2769 (9)	0.5355 (7)	0.1168 (7)	0.0309 (15)
H6	0.300993	0.627298	0.082925	0.037*
C8	0.1967 (9)	0.2193 (7)	0.0718 (8)	0.0293 (15)
H8	0.168542	0.101425	0.008264	0.035*
C1	0.2946 (8)	0.6892 (7)	0.6965 (7)	0.0211 (13)
C17	0.3516 (9)	0.8684 (7)	0.8114 (8)	0.0316 (15)
H17	0.344531	0.869089	0.900757	0.038*
C7	0.2402 (9)	0.3608 (7)	0.0253 (7)	0.0358 (15)
H7	0.244369	0.336192	−0.068749	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C15	0.021 (3)	0.017 (3)	0.019 (3)	0.0069 (19)	0.010 (3)	0.007 (3)
C16	0.020 (3)	0.017 (3)	0.023 (4)	0.006 (2)	0.008 (3)	0.006 (3)
O1	0.072 (3)	0.020 (2)	0.028 (3)	0.0000 (19)	0.017 (3)	−0.008 (2)
C2	0.019 (3)	0.015 (3)	0.019 (3)	0.0038 (18)	0.005 (3)	0.002 (3)
C12	0.024 (3)	0.020 (3)	0.017 (3)	0.009 (2)	0.008 (3)	0.009 (3)
C10	0.028 (3)	0.019 (3)	0.027 (4)	0.006 (2)	−0.001 (4)	0.006 (3)
C3	0.022 (3)	0.017 (3)	0.029 (4)	0.0028 (19)	0.002 (3)	0.006 (3)
C13	0.029 (3)	0.029 (3)	0.017 (3)	0.007 (2)	0.004 (3)	0.013 (3)
C5	0.026 (3)	0.020 (3)	0.019 (3)	0.006 (2)	0.007 (3)	0.006 (3)
C4	0.034 (3)	0.018 (3)	0.026 (4)	0.007 (2)	0.007 (4)	0.011 (3)
C11	0.027 (3)	0.016 (3)	0.025 (4)	0.007 (2)	0.004 (3)	0.009 (3)
C14	0.031 (3)	0.028 (3)	0.008 (3)	0.008 (2)	0.010 (3)	0.003 (3)
C9	0.022 (3)	0.020 (3)	0.024 (4)	0.005 (2)	0.001 (3)	0.003 (3)
C6	0.051 (4)	0.030 (3)	0.017 (3)	0.012 (3)	0.011 (4)	0.014 (3)
C8	0.039 (3)	0.023 (3)	0.019 (3)	0.009 (2)	0.003 (4)	−0.001 (3)
C1	0.023 (3)	0.022 (3)	0.014 (3)	0.007 (2)	0.007 (3)	0.001 (3)
C17	0.038 (3)	0.027 (3)	0.021 (4)	0.006 (2)	0.009 (4)	−0.001 (3)
C7	0.054 (4)	0.040 (4)	0.014 (3)	0.013 (3)	0.011 (4)	0.011 (3)

Geometric parameters (Å, º)

C15—C16	1.426 (9)	C13—C14	1.372 (8)
C15—C2	1.418 (8)	C5—C4	1.426 (8)
C15—C12	1.435 (6)	C5—C6	1.399 (9)
C16—C5	1.430 (6)	C4—H4	0.9300
C16—C9	1.413 (8)	C11—H11	0.9300
O1—C17	1.216 (6)	C14—H14	0.9300
C2—C3	1.444 (7)	C14—C1	1.403 (7)
C2—C1	1.417 (9)	C9—C8	1.407 (9)
C12—C13	1.392 (9)	C6—H6	0.9300
C12—C11	1.431 (8)	C6—C7	1.374 (8)
C10—H10	0.9300	C8—H8	0.9300
C10—C11	1.352 (9)	C8—C7	1.399 (7)
C10—C9	1.433 (7)	C1—C17	1.478 (8)
C3—H3	0.9300	C17—H17	0.9300
C3—C4	1.340 (9)	C7—H7	0.9300
C13—H13	0.9300
C16—C15—C12	118.8 (5)	C5—C4—H4	119.0
C2—C15—C16	120.5 (4)	C12—C11—H11	118.9
C2—C15—C12	120.8 (6)	C10—C11—C12	122.2 (5)
C15—C16—C5	119.6 (5)	C10—C11—H11	118.9
C9—C16—C15	120.8 (4)	C13—C14—H14	119.0
C9—C16—C5	119.6 (6)	C13—C14—C1	121.9 (6)
C15—C2—C3	118.0 (6)	C1—C14—H14	119.0
C1—C2—C15	117.9 (4)	C16—C9—C10	119.3 (6)
C1—C2—C3	124.1 (5)	C8—C9—C16	119.6 (5)
C13—C12—C15	119.1 (5)	C8—C9—C10	121.2 (6)
C13—C12—C11	122.2 (4)	C5—C6—H6	119.5
C11—C12—C15	118.6 (6)	C7—C6—C5	121.0 (5)
C11—C10—H10	119.8	C7—C6—H6	119.5
C11—C10—C9	120.3 (6)	C9—C8—H8	120.1
C9—C10—H10	119.8	C7—C8—C9	119.8 (6)
C2—C3—H3	119.3	C7—C8—H8	120.1
C4—C3—C2	121.5 (6)	C2—C1—C17	125.0 (5)
C4—C3—H3	119.3	C14—C1—C2	120.0 (5)
C12—C13—H13	119.9	C14—C1—C17	114.9 (6)
C14—C13—C12	120.2 (5)	O1—C17—C1	129.2 (6)
C14—C13—H13	119.9	O1—C17—H17	115.4
C4—C5—C16	118.3 (6)	C1—C17—H17	115.4
C6—C5—C16	119.0 (5)	C6—C7—C8	120.9 (6)
C6—C5—C4	122.7 (5)	C6—C7—H7	119.5
C3—C4—C5	122.1 (5)	C8—C7—H7	119.5
C3—C4—H4	119.0

(10kbar)

Crystal data

C17H10O	V = 506.95 (16) Å^3
Mr = 230.25	Z = 2
Triclinic, P1	F(000) = 240
a = 6.6950 (8) Å	Dx = 1.508 Mg m^−3
b = 8.1846 (11) Å	Synchrotron radiation, λ = 0.4859 Å
c = 10.306 (2) Å	Cell parameters from 1136 reflections
α = 109.649 (18)°	θ = 1.9–21.7°
β = 99.384 (16)°	µ = 0.05 mm^−1
γ = 100.652 (11)°	T = 293 K

Data collection

Dectris-CrysAlisPro-abstract goniometer imported dectris images diffractometer	1830 independent reflections
Radiation source: synchrotron	1190 reflections with I > 2σ(I)
Synchrotron monochromator	Rint = 0.093
ω scans	θmax = 22.7°, θmin = 1.9°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −10→10
Tmin = 0.216, Tmax = 1.000	k = −12→12
1830 measured reflections	l = −15→15

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.095	H-atom parameters constrained
wR(F^2) = 0.282	w = 1/[σ^2(Fo^2) + (0.1271P)^2 + 0.3938P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
1830 reflections	Δρmax = 0.55 e Å^−3
164 parameters	Δρmin = −0.39 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin.

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

	x	y	z	Uiso*/Ueq
C2	0.7115 (5)	0.3447 (5)	0.4477 (6)	0.0176 (10)
C12	0.7998 (5)	0.6699 (6)	0.4963 (7)	0.0187 (10)
C15	0.7566 (5)	0.5235 (5)	0.5442 (6)	0.0164 (10)
C5	0.7214 (5)	0.4225 (6)	0.7409 (7)	0.0239 (13)
C9	0.8057 (6)	0.7446 (6)	0.7857 (6)	0.0197 (10)
C4	0.6793 (6)	0.2425 (6)	0.6409 (7)	0.0217 (11)
H4	0.655284	0.148997	0.673094	0.026*
C11	0.8457 (6)	0.8496 (6)	0.5962 (8)	0.0261 (14)
H11	0.874676	0.943681	0.565017	0.031*
O1	0.5931 (5)	−0.0149 (5)	0.1943 (6)	0.0517 (14)
C16	0.7645 (5)	0.5661 (6)	0.6914 (7)	0.0197 (12)
C13	0.7932 (6)	0.6304 (6)	0.3531 (7)	0.0245 (12)
H13	0.819398	0.723898	0.320999	0.029*
C3	0.6727 (6)	0.2021 (6)	0.5014 (7)	0.0232 (12)
H3	0.643312	0.082879	0.439925	0.028*
C14	0.7486 (5)	0.4549 (6)	0.2574 (6)	0.0241 (10)
H14	0.748355	0.432819	0.162721	0.029*
C1	0.7032 (5)	0.3085 (6)	0.3012 (6)	0.0180 (9)
C10	0.8485 (6)	0.8877 (6)	0.7337 (7)	0.0232 (12)
H10	0.878044	1.006606	0.795782	0.028*
C6	0.7235 (7)	0.4631 (7)	0.8823 (7)	0.0303 (12)
H6	0.699537	0.370743	0.915787	0.036*
C17	0.6499 (6)	0.1337 (6)	0.1894 (7)	0.0307 (13)
H17	0.660150	0.133457	0.100434	0.037*
C8	0.8035 (6)	0.7811 (7)	0.9278 (7)	0.0295 (13)
H8	0.830323	0.899307	0.990807	0.035*
C7	0.7607 (7)	0.6396 (7)	0.9756 (7)	0.0359 (13)
H7	0.757314	0.664228	1.070054	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0164 (14)	0.018 (3)	0.016 (3)	0.0045 (15)	0.002 (2)	0.005 (3)
C12	0.0228 (16)	0.018 (3)	0.016 (3)	0.0071 (16)	0.004 (2)	0.007 (3)
C15	0.0196 (15)	0.016 (3)	0.014 (3)	0.0061 (16)	0.004 (2)	0.006 (3)
C5	0.0252 (17)	0.023 (3)	0.029 (4)	0.0075 (17)	0.007 (3)	0.016 (4)
C9	0.0242 (16)	0.022 (3)	0.013 (3)	0.0068 (17)	0.004 (2)	0.005 (3)
C4	0.0296 (18)	0.016 (2)	0.022 (3)	0.0055 (17)	0.008 (3)	0.010 (3)
C11	0.0286 (18)	0.019 (3)	0.039 (4)	0.0089 (17)	0.011 (3)	0.019 (4)
O1	0.072 (2)	0.025 (2)	0.053 (4)	0.0049 (17)	0.031 (3)	0.005 (3)
C16	0.0190 (15)	0.019 (3)	0.022 (3)	0.0047 (16)	0.004 (2)	0.010 (4)
C13	0.0299 (18)	0.025 (3)	0.025 (3)	0.0095 (18)	0.010 (3)	0.014 (4)
C3	0.0285 (18)	0.019 (3)	0.027 (4)	0.0077 (17)	0.012 (3)	0.012 (4)
C14	0.0320 (18)	0.032 (3)	0.014 (3)	0.0096 (18)	0.011 (2)	0.013 (3)
C1	0.0266 (17)	0.023 (3)	0.006 (2)	0.0100 (17)	0.010 (2)	0.004 (3)
C10	0.0315 (18)	0.016 (3)	0.020 (3)	0.0060 (17)	0.005 (3)	0.006 (3)
C6	0.049 (2)	0.034 (3)	0.015 (3)	0.009 (2)	0.007 (3)	0.019 (4)
C17	0.039 (2)	0.035 (3)	0.025 (3)	0.013 (2)	0.018 (3)	0.013 (4)
C8	0.038 (2)	0.024 (3)	0.024 (4)	0.010 (2)	0.009 (3)	0.004 (4)
C7	0.055 (3)	0.041 (3)	0.017 (3)	0.013 (2)	0.014 (3)	0.016 (4)

Geometric parameters (Å, º)

C2—C15	1.407 (7)	C11—C10	1.340 (9)
C2—C3	1.451 (5)	O1—C17	1.226 (5)
C2—C1	1.427 (8)	C13—H13	0.9300
C12—C15	1.442 (5)	C13—C14	1.385 (7)
C12—C11	1.425 (7)	C3—H3	0.9300
C12—C13	1.392 (9)	C14—H14	0.9300
C15—C16	1.427 (8)	C14—C1	1.417 (5)
C5—C4	1.429 (7)	C1—C17	1.439 (7)
C5—C16	1.432 (5)	C10—H10	0.9300
C5—C6	1.379 (9)	C6—H6	0.9300
C9—C16	1.401 (7)	C6—C7	1.389 (7)
C9—C10	1.446 (5)	C17—H17	0.9300
C9—C8	1.395 (9)	C8—H8	0.9300
C4—H4	0.9300	C8—C7	1.405 (6)
C4—C3	1.354 (9)	C7—H7	0.9300
C11—H11	0.9300
C15—C2—C3	118.3 (5)	C14—C13—H13	119.3
C15—C2—C1	119.7 (4)	C2—C3—H3	120.0
C1—C2—C3	122.0 (5)	C4—C3—C2	120.0 (5)
C11—C12—C15	119.2 (5)	C4—C3—H3	120.0
C13—C12—C15	118.6 (5)	C13—C14—H14	119.5
C13—C12—C11	122.1 (4)	C13—C14—C1	121.1 (5)
C2—C15—C12	120.3 (5)	C1—C14—H14	119.5
C2—C15—C16	121.7 (4)	C2—C1—C17	126.1 (4)
C16—C15—C12	118.0 (4)	C14—C1—C2	118.8 (4)
C4—C5—C16	118.2 (5)	C14—C1—C17	115.1 (5)
C6—C5—C4	122.8 (4)	C9—C10—H10	119.9
C6—C5—C16	119.0 (5)	C11—C10—C9	120.3 (5)
C16—C9—C10	119.2 (5)	C11—C10—H10	119.9
C8—C9—C16	119.6 (4)	C5—C6—H6	119.4
C8—C9—C10	121.2 (5)	C5—C6—C7	121.1 (4)
C5—C4—H4	118.5	C7—C6—H6	119.4
C3—C4—C5	122.9 (4)	O1—C17—C1	129.5 (6)
C3—C4—H4	118.5	O1—C17—H17	115.3
C12—C11—H11	118.9	C1—C17—H17	115.3
C10—C11—C12	122.2 (4)	C9—C8—H8	120.0
C10—C11—H11	118.9	C9—C8—C7	120.1 (5)
C15—C16—C5	118.8 (5)	C7—C8—H8	120.0
C9—C16—C15	121.1 (4)	C6—C7—C8	120.2 (5)
C9—C16—C5	120.1 (5)	C6—C7—H7	119.9
C12—C13—H13	119.3	C8—C7—H7	119.9
C14—C13—C12	121.4 (4)

(15kbar)

Crystal data

C17H10O	V = 495.3 (2) Å^3
Mr = 230.25	Z = 2
Triclinic, P1	F(000) = 240
a = 6.6139 (17) Å	Dx = 1.544 Mg m^−3
b = 8.1151 (16) Å	Synchrotron radiation, λ = 0.4859 Å
c = 10.272 (2) Å	Cell parameters from 599 reflections
α = 109.439 (19)°	θ = 1.9–21.4°
β = 99.563 (19)°	µ = 0.05 mm^−1
γ = 100.637 (19)°	T = 293 K

Data collection

Dectris-CrysAlisPro-abstract goniometer imported dectris images diffractometer	1747 independent reflections
Radiation source: synchrotron	912 reflections with I > 2σ(I)
Synchrotron monochromator	Rint = 0.082
ω scans	θmax = 22.6°, θmin = 1.9°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −10→10
Tmin = 0.729, Tmax = 1.000	k = −12→12
1747 measured reflections	l = −14→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.080	H-atom parameters constrained
wR(F^2) = 0.239	w = 1/[σ^2(Fo^2) + (0.1346P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1747 reflections	Δρmax = 0.41 e Å^−3
164 parameters	Δρmin = −0.31 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin.

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

	x	y	z	Uiso*/Ueq
O1	0.4089 (5)	1.0167 (3)	0.8073 (3)	0.0489 (13)
C2	0.2906 (6)	0.6581 (4)	0.5544 (4)	0.0235 (13)
C15	0.2410 (5)	0.4741 (4)	0.4568 (4)	0.0230 (14)
C1	0.2956 (6)	0.6902 (4)	0.6994 (4)	0.0236 (13)
C13	0.2052 (6)	0.3672 (5)	0.6494 (5)	0.0273 (14)
H13	0.178572	0.273466	0.682316	0.033*
C4	0.3216 (6)	0.7594 (4)	0.3578 (5)	0.0279 (14)
H4	0.347449	0.853373	0.325101	0.033*
C11	0.1521 (6)	0.1462 (4)	0.4046 (5)	0.0279 (14)
H11	0.122498	0.050892	0.435456	0.033*
C12	0.1995 (6)	0.3290 (4)	0.5052 (5)	0.0232 (13)
C14	0.2508 (6)	0.5452 (4)	0.7427 (4)	0.0319 (14)
H14	0.251578	0.568626	0.837839	0.038*
C8	0.1958 (7)	0.2180 (5)	0.0708 (5)	0.0321 (15)
H8	0.169235	0.099237	0.007483	0.038*
C16	0.2367 (6)	0.4347 (4)	0.3098 (4)	0.0215 (13)
C9	0.1920 (6)	0.2515 (4)	0.2127 (4)	0.0260 (14)
C7	0.2381 (7)	0.3574 (5)	0.0225 (5)	0.0384 (15)
H7	0.241035	0.331644	−0.072348	0.046*
C3	0.3265 (6)	0.7982 (4)	0.4980 (4)	0.0245 (13)
H3	0.353838	0.918322	0.558785	0.029*
C10	0.1497 (6)	0.1103 (4)	0.2658 (5)	0.0288 (14)
H10	0.119694	−0.009394	0.203462	0.035*
C17	0.3530 (6)	0.8689 (5)	0.8154 (4)	0.0378 (16)
H17	0.346087	0.869549	0.905209	0.045*
C5	0.2771 (6)	0.5764 (4)	0.2596 (4)	0.0228 (13)
C6	0.2764 (7)	0.5362 (5)	0.1147 (5)	0.0346 (16)
H6	0.301396	0.629232	0.080899	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.077 (2)	0.0231 (14)	0.038 (2)	0.0025 (13)	0.026 (2)	0.0014 (13)
C2	0.024 (2)	0.0228 (17)	0.021 (3)	0.0044 (13)	0.007 (2)	0.0044 (16)
C15	0.026 (2)	0.0181 (16)	0.024 (3)	0.0049 (13)	0.012 (2)	0.0048 (15)
C1	0.025 (2)	0.0240 (17)	0.021 (3)	0.0063 (14)	0.007 (2)	0.0067 (16)
C13	0.031 (2)	0.0313 (18)	0.023 (3)	0.0067 (15)	0.008 (3)	0.0155 (17)
C4	0.037 (2)	0.0196 (16)	0.031 (3)	0.0067 (14)	0.012 (3)	0.0127 (16)
C11	0.033 (2)	0.0201 (17)	0.033 (3)	0.0050 (14)	0.011 (3)	0.0120 (17)
C12	0.027 (2)	0.0207 (16)	0.022 (3)	0.0045 (13)	0.008 (2)	0.0090 (15)
C14	0.041 (2)	0.030 (2)	0.025 (3)	0.0100 (16)	0.015 (3)	0.0074 (17)
C8	0.042 (3)	0.0249 (19)	0.025 (3)	0.0064 (15)	0.009 (3)	0.0048 (18)
C16	0.027 (2)	0.0201 (16)	0.018 (3)	0.0084 (14)	0.006 (2)	0.0073 (15)
C9	0.027 (2)	0.0250 (18)	0.022 (3)	0.0061 (14)	0.004 (2)	0.0057 (16)
C7	0.060 (3)	0.035 (2)	0.019 (3)	0.0095 (18)	0.011 (3)	0.0094 (18)
C3	0.032 (2)	0.0164 (15)	0.024 (3)	0.0043 (13)	0.006 (3)	0.0086 (15)
C10	0.037 (2)	0.0150 (15)	0.031 (3)	0.0078 (14)	0.008 (3)	0.0047 (15)
C17	0.049 (3)	0.029 (2)	0.032 (3)	0.0071 (17)	0.021 (3)	0.0034 (18)
C5	0.026 (2)	0.0231 (17)	0.019 (3)	0.0041 (13)	0.004 (2)	0.0092 (16)
C6	0.051 (3)	0.031 (2)	0.025 (3)	0.0099 (17)	0.011 (3)	0.0142 (18)

Geometric parameters (Å, º)

O1—C17	1.223 (4)	C11—C10	1.354 (6)
C2—C15	1.434 (4)	C14—H14	0.9300
C2—C1	1.418 (6)	C8—H8	0.9300
C2—C3	1.439 (6)	C8—C9	1.396 (6)
C15—C12	1.423 (6)	C8—C7	1.382 (6)
C15—C16	1.430 (5)	C16—C9	1.430 (4)
C1—C14	1.391 (5)	C16—C5	1.408 (5)
C1—C17	1.470 (4)	C9—C10	1.428 (6)
C13—H13	0.9300	C7—H7	0.9300
C13—C12	1.402 (6)	C7—C6	1.391 (4)
C13—C14	1.385 (4)	C3—H3	0.9300
C4—H4	0.9300	C10—H10	0.9300
C4—C3	1.361 (6)	C17—H17	0.9300
C4—C5	1.433 (4)	C5—C6	1.413 (6)
C11—H11	0.9300	C6—H6	0.9300
C11—C12	1.438 (4)
C15—C2—C3	117.8 (3)	C7—C8—C9	121.4 (3)
C1—C2—C15	118.0 (4)	C9—C16—C15	120.3 (4)
C1—C2—C3	124.2 (3)	C5—C16—C15	120.2 (3)
C12—C15—C2	120.6 (3)	C5—C16—C9	119.5 (3)
C12—C15—C16	119.3 (3)	C8—C9—C16	118.9 (4)
C16—C15—C2	120.1 (4)	C8—C9—C10	122.6 (3)
C2—C1—C17	125.6 (4)	C10—C9—C16	118.5 (3)
C14—C1—C2	119.9 (3)	C8—C7—H7	119.8
C14—C1—C17	114.4 (3)	C8—C7—C6	120.5 (4)
C12—C13—H13	120.2	C6—C7—H7	119.8
C14—C13—H13	120.2	C2—C3—H3	119.2
C14—C13—C12	119.6 (4)	C4—C3—C2	121.6 (3)
C3—C4—H4	119.4	C4—C3—H3	119.2
C3—C4—C5	121.2 (4)	C11—C10—C9	121.6 (3)
C5—C4—H4	119.4	C11—C10—H10	119.2
C12—C11—H11	119.4	C9—C10—H10	119.2
C10—C11—H11	119.4	O1—C17—C1	127.5 (4)
C10—C11—C12	121.2 (4)	O1—C17—H17	116.3
C15—C12—C11	119.1 (3)	C1—C17—H17	116.3
C13—C12—C15	119.4 (3)	C16—C5—C4	119.1 (3)
C13—C12—C11	121.5 (4)	C16—C5—C6	119.7 (3)
C1—C14—H14	118.8	C6—C5—C4	121.2 (4)
C13—C14—C1	122.4 (4)	C7—C6—C5	120.0 (4)
C13—C14—H14	118.8	C7—C6—H6	120.0
C9—C8—H8	119.3	C5—C6—H6	120.0
C7—C8—H8	119.3

(18kbar)

Crystal data

C17H10O	V = 492.5 (2) Å^3
Mr = 230.25	Z = 2
Triclinic, P1	F(000) = 240
a = 6.6007 (14) Å	Dx = 1.553 Mg m^−3
b = 8.1331 (19) Å	Synchrotron radiation, λ = 0.4859 Å
c = 10.232 (3) Å	Cell parameters from 615 reflections
α = 109.52 (3)°	θ = 1.9–22.0°
β = 99.88 (3)°	µ = 0.05 mm^−1
γ = 100.617 (18)°	T = 293 K

Data collection

Dectris-CrysAlisPro-abstract goniometer imported dectris images diffractometer	1700 independent reflections
Radiation source: synchrotron	1100 reflections with I > 2σ(I)
Synchrotron monochromator	Rint = 0.134
ω scans	θmax = 22.7°, θmin = 1.9°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −10→10
Tmin = 0.364, Tmax = 1.000	k = −12→12
1700 measured reflections	l = −15→15

Refinement

Refinement on F^2	162 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.224	H-atom parameters constrained
wR(F^2) = 0.502	w = 1/[σ^2(Fo^2) + (0.1062P)^2 + 5.7717P] where P = (Fo^2 + 2Fc^2)/3
S = 1.18	(Δ/σ)max < 0.001
1700 reflections	Δρmax = 1.24 e Å^−3
164 parameters	Δρmin = −0.78 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin.

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

	x	y	z	Uiso*/Ueq
C2	0.7116 (14)	0.3460 (15)	0.4505 (17)	0.0104 (13)
O1	0.5880 (17)	−0.0193 (14)	0.1877 (18)	0.045 (3)
C4	0.6781 (19)	0.2427 (16)	0.6416 (19)	0.022 (2)
H4	0.651502	0.148658	0.673879	0.026*
C12	0.7987 (18)	0.6692 (17)	0.492 (2)	0.0212 (19)
C11	0.8474 (17)	0.8524 (16)	0.5957 (19)	0.0198 (19)
H11	0.877751	0.947771	0.565212	0.024*
C15	0.7554 (17)	0.5249 (16)	0.5423 (19)	0.0176 (18)
C5	0.7210 (16)	0.4235 (16)	0.7425 (18)	0.0159 (17)
C9	0.8079 (19)	0.7464 (17)	0.7843 (19)	0.022 (2)
C16	0.7672 (16)	0.5644 (16)	0.6889 (18)	0.0165 (17)
C14	0.7491 (17)	0.4552 (16)	0.2544 (19)	0.0205 (19)
H14	0.749497	0.435234	0.159539	0.025*
C3	0.6741 (17)	0.2026 (16)	0.5067 (18)	0.0183 (19)
H3	0.647452	0.082467	0.445858	0.022*
C13	0.7950 (19)	0.6338 (17)	0.355 (2)	0.022 (2)
H13	0.823565	0.729405	0.325086	0.027*
C6	0.728 (2)	0.4647 (19)	0.8921 (19)	0.027 (2)
H6	0.707952	0.373237	0.927747	0.032*
C1	0.7028 (18)	0.3072 (16)	0.2966 (19)	0.0188 (18)
C8	0.8037 (19)	0.7803 (18)	0.9246 (19)	0.023 (2)
H8	0.828112	0.899528	0.986703	0.027*
C10	0.8503 (17)	0.8898 (17)	0.7355 (19)	0.0193 (18)
H10	0.880047	1.008923	0.798976	0.023*
C7	0.763 (2)	0.6404 (18)	0.979 (2)	0.031 (3)
H7	0.761510	0.669753	1.075153	0.037*
C17	0.649 (2)	0.1360 (18)	0.191 (2)	0.029 (2)
H17	0.660374	0.137764	0.102136	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.004 (3)	0.016 (2)	0.012 (2)	0.001 (2)	0.002 (3)	0.007 (2)
O1	0.076 (7)	0.021 (3)	0.041 (9)	0.007 (4)	0.034 (8)	0.007 (4)
C4	0.037 (6)	0.015 (3)	0.012 (3)	0.000 (3)	0.007 (4)	0.007 (3)
C12	0.032 (5)	0.018 (2)	0.021 (3)	0.009 (3)	0.012 (4)	0.013 (3)
C11	0.029 (5)	0.017 (2)	0.022 (3)	0.008 (3)	0.012 (4)	0.013 (3)
C15	0.025 (5)	0.015 (2)	0.012 (2)	0.002 (2)	0.001 (3)	0.008 (2)
C5	0.020 (4)	0.016 (2)	0.010 (3)	0.001 (3)	0.000 (3)	0.006 (3)
C9	0.036 (6)	0.016 (2)	0.012 (3)	0.001 (3)	0.005 (4)	0.007 (2)
C16	0.020 (4)	0.016 (2)	0.011 (2)	0.000 (3)	−0.001 (3)	0.007 (2)
C14	0.028 (5)	0.021 (2)	0.021 (4)	0.008 (3)	0.014 (4)	0.014 (3)
C3	0.028 (5)	0.015 (3)	0.012 (3)	0.001 (3)	0.005 (4)	0.007 (3)
C13	0.034 (5)	0.020 (3)	0.021 (3)	0.009 (3)	0.013 (4)	0.014 (3)
C6	0.045 (7)	0.023 (3)	0.011 (3)	0.006 (4)	0.006 (4)	0.008 (3)
C1	0.027 (5)	0.018 (2)	0.013 (2)	0.004 (3)	0.006 (3)	0.009 (2)
C8	0.033 (6)	0.023 (3)	0.012 (3)	0.005 (4)	0.005 (4)	0.008 (3)
C10	0.024 (5)	0.019 (3)	0.021 (3)	0.007 (3)	0.011 (4)	0.012 (3)
C7	0.059 (8)	0.023 (3)	0.012 (4)	0.006 (4)	0.010 (5)	0.008 (3)
C17	0.040 (6)	0.021 (2)	0.021 (4)	0.002 (3)	0.007 (5)	0.003 (3)

Geometric parameters (Å, º)

C2—C15	1.386 (18)	C9—C8	1.38 (2)
C2—C3	1.464 (15)	C9—C10	1.416 (15)
C2—C1	1.49 (2)	C14—H14	0.9300
O1—C17	1.240 (14)	C14—C13	1.41 (2)
C4—H4	0.9300	C14—C1	1.409 (14)
C4—C5	1.43 (2)	C3—H3	0.9300
C4—C3	1.30 (2)	C13—H13	0.9300
C12—C11	1.45 (2)	C6—H6	0.9300
C12—C15	1.433 (15)	C6—C7	1.36 (2)
C12—C13	1.33 (3)	C1—C17	1.38 (2)
C11—H11	0.9300	C8—H8	0.9300
C11—C10	1.35 (3)	C8—C7	1.431 (17)
C15—C16	1.41 (2)	C10—H10	0.9300
C5—C16	1.434 (15)	C7—H7	0.9300
C5—C6	1.44 (2)	C17—H17	0.9300
C9—C16	1.419 (19)
C15—C2—C3	119.6 (14)	C1—C14—C13	120.4 (15)
C15—C2—C1	118.1 (10)	C2—C3—H3	119.9
C3—C2—C1	122.3 (12)	C4—C3—C2	120.2 (14)
C5—C4—H4	118.2	C4—C3—H3	119.9
C3—C4—H4	118.2	C12—C13—C14	122.1 (11)
C3—C4—C5	123.5 (11)	C12—C13—H13	119.0
C15—C12—C11	117.7 (15)	C14—C13—H13	119.0
C13—C12—C11	122.0 (11)	C5—C6—H6	120.8
C13—C12—C15	120.3 (15)	C7—C6—C5	118.3 (12)
C12—C11—H11	118.8	C7—C6—H6	120.8
C10—C11—C12	122.3 (10)	C14—C1—C2	117.8 (13)
C10—C11—H11	118.8	C17—C1—C2	124.7 (10)
C2—C15—C12	121.2 (15)	C17—C1—C14	117.4 (15)
C2—C15—C16	118.9 (10)	C9—C8—H8	118.5
C16—C15—C12	119.8 (13)	C9—C8—C7	122.9 (14)
C4—C5—C16	116.3 (13)	C7—C8—H8	118.5
C4—C5—C6	122.5 (10)	C11—C10—C9	119.6 (14)
C16—C5—C6	121.2 (13)	C11—C10—H10	120.2
C8—C9—C16	118.6 (11)	C9—C10—H10	120.2
C8—C9—C10	120.8 (14)	C6—C7—C8	120.2 (15)
C10—C9—C16	120.6 (15)	C6—C7—H7	119.9
C15—C16—C5	121.3 (13)	C8—C7—H7	119.9
C15—C16—C9	119.8 (10)	O1—C17—C1	134.6 (19)
C9—C16—C5	118.6 (14)	O1—C17—H17	112.7
C13—C14—H14	119.8	C1—C17—H17	112.7
C1—C14—H14	119.8

(28kbar)

Crystal data

C17H10O	V = 477.5 (3) Å^3
Mr = 230.25	Z = 2
Triclinic, P1	F(000) = 240
a = 6.477 (2) Å	Dx = 1.601 Mg m^−3
b = 8.041 (2) Å	Synchrotron radiation, λ = 0.4859 Å
c = 10.205 (3) Å	Cell parameters from 460 reflections
α = 109.37 (3)°	θ = 1.9–21.6°
β = 99.57 (3)°	µ = 0.05 mm^−1
γ = 100.71 (3)°	T = 293 K

Data collection

Dectris-CrysAlisPro-abstract goniometer imported dectris images diffractometer	2461 independent reflections
Radiation source: synchrotron	1176 reflections with I > 2σ(I)
Synchrotron monochromator	Rint = 0.139
ω scans	θmax = 22.6°, θmin = 1.9°
Absorption correction: multi-scan CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −9→9
Tmin = 0.074, Tmax = 1.000	k = −12→12
2461 measured reflections	l = −15→15

Refinement

Refinement on F^2	162 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.169	H-atom parameters constrained
wR(F^2) = 0.434	w = 1/[σ^2(Fo^2) + (0.1308P)^2 + 1.3113P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
2461 reflections	Δρmax = 0.88 e Å^−3
165 parameters	Δρmin = −0.78 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 3-component twin.

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

	x	y	z	Uiso*/Ueq
O1	0.4123 (13)	1.0195 (7)	0.8106 (7)	0.051 (3)
C15	0.2386 (15)	0.4739 (8)	0.4567 (8)	0.025 (2)
C2	0.2922 (15)	0.6599 (8)	0.5555 (9)	0.024 (2)
C3	0.3270 (15)	0.8004 (9)	0.4982 (9)	0.027 (2)
H3	0.352128	0.921479	0.558694	0.032*
C14	0.2495 (17)	0.5447 (10)	0.7444 (10)	0.038 (3)
H14	0.247617	0.567838	0.839700	0.045*
C1	0.2971 (15)	0.6893 (9)	0.7015 (9)	0.027 (2)
C12	0.1973 (13)	0.3275 (9)	0.5046 (9)	0.0194 (17)
C9	0.1925 (15)	0.2501 (10)	0.2132 (9)	0.027 (2)
C8	0.1963 (16)	0.2154 (10)	0.0695 (9)	0.030 (3)
H8	0.173563	0.095818	0.006498	0.036*
C5	0.2758 (16)	0.5774 (9)	0.2575 (9)	0.029 (3)
C6	0.2769 (17)	0.5366 (10)	0.1135 (10)	0.035 (3)
H6	0.307239	0.631026	0.080507	0.042*
C7	0.2338 (17)	0.3584 (11)	0.0195 (9)	0.034 (3)
H7	0.229641	0.333058	−0.076795	0.040*
C4	0.3241 (16)	0.7606 (9)	0.3577 (9)	0.031 (3)
H4	0.354545	0.855918	0.325630	0.037*
C16	0.2370 (15)	0.4318 (9)	0.3099 (9)	0.025 (2)
C13	0.2043 (14)	0.3656 (9)	0.6500 (9)	0.0214 (19)
H13	0.178723	0.270620	0.682972	0.026*
C11	0.1480 (15)	0.1434 (9)	0.4033 (9)	0.027 (2)
H11	0.116643	0.047136	0.434229	0.032*
C17	0.3558 (17)	0.8699 (9)	0.8171 (9)	0.038 (3)
H17	0.349050	0.870074	0.907486	0.045*
C10	0.1461 (17)	0.1070 (10)	0.2636 (10)	0.036 (3)
H10	0.113970	−0.013419	0.200166	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.091 (6)	0.017 (2)	0.036 (4)	0.002 (3)	0.029 (5)	0.001 (2)
C15	0.039 (6)	0.012 (3)	0.022 (4)	0.002 (3)	0.012 (4)	0.004 (2)
C2	0.035 (5)	0.013 (3)	0.024 (4)	0.004 (3)	0.011 (4)	0.008 (2)
C3	0.038 (6)	0.017 (3)	0.026 (4)	0.002 (3)	0.011 (4)	0.011 (3)
C14	0.058 (7)	0.024 (3)	0.031 (5)	0.004 (4)	0.023 (5)	0.008 (3)
C1	0.040 (6)	0.018 (3)	0.027 (4)	0.009 (3)	0.019 (4)	0.008 (2)
C12	0.018 (4)	0.022 (2)	0.021 (3)	0.009 (2)	0.000 (3)	0.012 (2)
C9	0.034 (6)	0.025 (3)	0.024 (4)	0.007 (3)	0.008 (4)	0.010 (3)
C8	0.045 (6)	0.022 (3)	0.025 (4)	0.008 (3)	0.015 (5)	0.009 (3)
C5	0.046 (6)	0.017 (3)	0.026 (4)	0.005 (3)	0.018 (5)	0.006 (2)
C6	0.053 (7)	0.028 (4)	0.026 (5)	0.008 (4)	0.011 (5)	0.013 (3)
C7	0.055 (7)	0.037 (4)	0.009 (4)	0.011 (4)	0.004 (5)	0.009 (3)
C4	0.050 (7)	0.017 (3)	0.030 (4)	0.003 (3)	0.021 (5)	0.010 (3)
C16	0.037 (6)	0.017 (3)	0.022 (4)	0.006 (3)	0.010 (4)	0.008 (2)
C13	0.029 (5)	0.021 (3)	0.024 (4)	0.014 (3)	0.003 (4)	0.018 (3)
C11	0.043 (6)	0.012 (3)	0.035 (5)	0.008 (3)	0.015 (5)	0.017 (3)
C17	0.068 (7)	0.017 (3)	0.029 (5)	0.010 (3)	0.028 (6)	0.004 (3)
C10	0.065 (7)	0.014 (3)	0.031 (5)	0.009 (3)	0.022 (5)	0.007 (3)

Geometric parameters (Å, º)

O1—C17	1.218 (10)	C9—C10	1.412 (13)
C15—C2	1.437 (8)	C8—H8	0.9300
C15—C12	1.416 (12)	C8—C7	1.402 (14)
C15—C16	1.420 (11)	C5—C6	1.397 (12)
C2—C3	1.434 (12)	C5—C4	1.427 (8)
C2—C1	1.423 (12)	C5—C16	1.439 (13)
C3—H3	0.9300	C6—H6	0.9300
C3—C4	1.358 (11)	C6—C7	1.379 (10)
C14—H14	0.9300	C7—H7	0.9300
C14—C1	1.374 (13)	C4—H4	0.9300
C14—C13	1.385 (9)	C13—H13	0.9300
C1—C17	1.468 (8)	C11—H11	0.9300
C12—C13	1.403 (12)	C11—C10	1.355 (12)
C12—C11	1.436 (8)	C17—H17	0.9300
C9—C8	1.405 (12)	C10—H10	0.9300
C9—C16	1.409 (8)
C12—C15—C2	120.8 (7)	C4—C5—C16	118.2 (7)
C12—C15—C16	118.1 (6)	C5—C6—H6	119.5
C16—C15—C2	121.0 (7)	C7—C6—C5	121.0 (9)
C3—C2—C15	117.5 (7)	C7—C6—H6	119.5
C1—C2—C15	117.2 (7)	C8—C7—H7	120.1
C1—C2—C3	125.3 (6)	C6—C7—C8	119.9 (8)
C2—C3—H3	119.2	C6—C7—H7	120.1
C4—C3—C2	121.5 (6)	C3—C4—C5	122.2 (8)
C4—C3—H3	119.2	C3—C4—H4	118.9
C1—C14—H14	119.0	C5—C4—H4	118.9
C1—C14—C13	122.0 (7)	C15—C16—C5	119.4 (6)
C13—C14—H14	119.0	C9—C16—C15	121.5 (8)
C2—C1—C17	124.3 (7)	C9—C16—C5	119.1 (7)
C14—C1—C2	120.8 (6)	C14—C13—C12	119.9 (8)
C14—C1—C17	114.8 (7)	C14—C13—H13	120.1
C15—C12—C11	119.3 (7)	C12—C13—H13	120.1
C13—C12—C15	119.3 (6)	C12—C11—H11	119.3
C13—C12—C11	121.4 (8)	C10—C11—C12	121.4 (8)
C8—C9—C16	119.4 (8)	C10—C11—H11	119.3
C8—C9—C10	121.6 (6)	O1—C17—C1	128.7 (8)
C16—C9—C10	119.1 (7)	O1—C17—H17	115.7
C9—C8—H8	119.5	C1—C17—H17	115.7
C7—C8—C9	120.9 (6)	C9—C10—H10	119.7
C7—C8—H8	119.5	C11—C10—C9	120.7 (6)
C6—C5—C4	122.2 (8)	C11—C10—H10	119.7
C6—C5—C16	119.5 (6)