2-Phenyl-2,3-dihydro-phenanthro[9,10-b][1,4]dioxine.

In the title compound, C(22)H(16)O(2), the phenanthrene ring system is essentially planar [maximum deviation = 0.058 (1) Å] and is inclined at an angle of 58.39 (6)° to the phenyl ring. The 1,4-dioxane ring is in a chair conformation. In the crystal, mol-ecules are stacked along the b axis, but no significant hydrogen bonds are observed.

Related literature

For general background to and details of the biological activity of phenanthrene derivatives, see: Wang et al. (2010 ▶); Li & Wang (2009 ▶); Gao & Wong (2010 ▶); Zhan & Jiang (2010 ▶); Becker & Dettbarn (2009 ▶); Jones & Mathews (1997 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C22H16O2

M = 312.35

Monoclinic,

a = 12.1831 (3) Å

b = 5.4674 (1) Å

c = 24.6064 (7) Å

β = 106.005 (2)°

V = 1575.50 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.49 × 0.41 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.960, T max = 0.989

17018 measured reflections

4613 independent reflections

2927 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.145

S = 1.04

4613 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003904/sj5097sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003904/sj5097Isup2.hkl

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

C22H16O2	F(000) = 656
Mr = 312.35	Dx = 1.317 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4055 reflections
a = 12.1831 (3) Å	θ = 2.8–28.1°
b = 5.4674 (1) Å	µ = 0.08 mm−1
c = 24.6064 (7) Å	T = 296 K
β = 106.005 (2)°	Plate, colourless
V = 1575.50 (7) Å3	0.49 × 0.41 × 0.13 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	4613 independent reflections
Radiation source: fine-focus sealed tube	2927 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 30.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→17
Tmin = 0.960, Tmax = 0.989	k = −7→7
17018 measured reflections	l = −34→34

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0666P)2 + 0.1135P] where P = (Fo2 + 2Fc2)/3
4613 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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. 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 > 2sigma(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	0.69332 (7)	0.38054 (17)	0.93970 (4)	0.0546 (2)
O2	0.88773 (8)	0.39205 (19)	0.89709 (4)	0.0634 (3)
C1	0.70209 (14)	−0.0387 (3)	1.00451 (6)	0.0650 (4)
H1A	0.6455	−0.0275	0.9704	0.078*
C2	0.69661 (18)	−0.2210 (3)	1.04270 (7)	0.0778 (5)
H2A	0.6366	−0.3325	1.0340	0.093*
C3	0.77931 (18)	−0.2381 (3)	1.09335 (7)	0.0790 (5)
H3A	0.7755	−0.3612	1.1189	0.095*
C4	0.86718 (15)	−0.0739 (3)	1.10617 (7)	0.0779 (5)
H4A	0.9232	−0.0854	1.1405	0.093*
C5	0.87316 (13)	0.1090 (3)	1.06854 (6)	0.0643 (4)
H5A	0.9327	0.2215	1.0778	0.077*
C6	0.79093 (11)	0.1262 (2)	1.01686 (5)	0.0502 (3)
C7	0.80427 (11)	0.3130 (2)	0.97448 (5)	0.0504 (3)
H7A	0.8427	0.4579	0.9944	0.060*
C8	0.87275 (12)	0.2128 (3)	0.93669 (6)	0.0590 (3)
H8A	0.9470	0.1598	0.9598	0.071*
H8B	0.8338	0.0716	0.9164	0.071*
C9	0.79160 (10)	0.5302 (2)	0.87464 (5)	0.0501 (3)
C10	0.79662 (11)	0.6914 (2)	0.82942 (5)	0.0505 (3)
C11	0.89116 (12)	0.6902 (3)	0.80716 (6)	0.0619 (4)
H11A	0.9501	0.5790	0.8208	0.074*
C12	0.89711 (14)	0.8519 (3)	0.76553 (6)	0.0706 (4)
H12A	0.9596	0.8491	0.7507	0.085*
C13	0.81042 (15)	1.0190 (3)	0.74551 (6)	0.0706 (4)
H13A	0.8158	1.1311	0.7179	0.085*
C14	0.71683 (14)	1.0214 (3)	0.76584 (6)	0.0639 (4)
H14A	0.6590	1.1344	0.7516	0.077*
C15	0.70603 (11)	0.8569 (2)	0.80781 (5)	0.0511 (3)
C16	0.60599 (11)	0.8495 (2)	0.82931 (5)	0.0500 (3)
C17	0.51242 (13)	1.0099 (3)	0.81093 (6)	0.0629 (4)
H17A	0.5139	1.1283	0.7840	0.075*
C18	0.41948 (13)	0.9955 (3)	0.83177 (6)	0.0669 (4)
H18A	0.3593	1.1047	0.8192	0.080*
C19	0.41436 (12)	0.8191 (3)	0.87158 (6)	0.0626 (4)
H19A	0.3503	0.8082	0.8850	0.075*
C20	0.50375 (11)	0.6612 (3)	0.89093 (6)	0.0545 (3)
H20A	0.5000	0.5429	0.9175	0.065*
C21	0.60128 (10)	0.6763 (2)	0.87100 (5)	0.0473 (3)
C22	0.69876 (10)	0.5239 (2)	0.89464 (5)	0.0479 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0505 (5)	0.0640 (5)	0.0521 (5)	0.0110 (4)	0.0191 (4)	0.0106 (4)
O2	0.0592 (6)	0.0747 (6)	0.0649 (6)	0.0212 (5)	0.0314 (5)	0.0178 (5)
C1	0.0845 (10)	0.0617 (8)	0.0518 (7)	−0.0079 (7)	0.0238 (7)	−0.0085 (7)
C2	0.1138 (13)	0.0596 (8)	0.0736 (10)	−0.0131 (9)	0.0484 (10)	−0.0079 (8)
C3	0.1175 (15)	0.0642 (9)	0.0705 (10)	0.0252 (10)	0.0512 (10)	0.0158 (8)
C4	0.0789 (11)	0.0925 (12)	0.0645 (9)	0.0307 (10)	0.0234 (8)	0.0236 (9)
C5	0.0577 (8)	0.0761 (9)	0.0595 (8)	0.0153 (7)	0.0166 (6)	0.0094 (7)
C6	0.0571 (7)	0.0507 (7)	0.0471 (6)	0.0110 (6)	0.0216 (6)	−0.0017 (5)
C7	0.0521 (7)	0.0520 (7)	0.0476 (7)	0.0079 (5)	0.0147 (5)	0.0002 (5)
C8	0.0630 (8)	0.0620 (8)	0.0576 (8)	0.0183 (6)	0.0258 (6)	0.0086 (7)
C9	0.0507 (7)	0.0542 (7)	0.0468 (6)	0.0081 (5)	0.0160 (5)	−0.0011 (6)
C10	0.0575 (7)	0.0538 (7)	0.0424 (6)	−0.0003 (6)	0.0173 (5)	−0.0052 (5)
C11	0.0644 (9)	0.0720 (9)	0.0546 (8)	0.0038 (7)	0.0255 (6)	0.0002 (7)
C12	0.0743 (10)	0.0852 (11)	0.0600 (8)	−0.0074 (8)	0.0315 (7)	0.0007 (8)
C13	0.0871 (11)	0.0733 (9)	0.0535 (8)	−0.0100 (9)	0.0229 (8)	0.0090 (7)
C14	0.0744 (9)	0.0633 (8)	0.0523 (7)	0.0020 (7)	0.0147 (7)	0.0060 (7)
C15	0.0603 (8)	0.0519 (7)	0.0394 (6)	−0.0017 (6)	0.0108 (5)	−0.0051 (5)
C16	0.0543 (7)	0.0515 (7)	0.0410 (6)	0.0038 (5)	0.0078 (5)	−0.0060 (5)
C17	0.0700 (9)	0.0598 (8)	0.0545 (8)	0.0120 (7)	0.0098 (7)	0.0025 (7)
C18	0.0609 (9)	0.0694 (9)	0.0664 (9)	0.0197 (7)	0.0106 (7)	−0.0024 (8)
C19	0.0508 (8)	0.0738 (9)	0.0620 (8)	0.0089 (7)	0.0136 (6)	−0.0084 (7)
C20	0.0506 (7)	0.0608 (8)	0.0518 (7)	0.0042 (6)	0.0139 (6)	−0.0028 (6)
C21	0.0477 (7)	0.0501 (6)	0.0425 (6)	0.0027 (5)	0.0095 (5)	−0.0068 (5)
C22	0.0522 (7)	0.0505 (6)	0.0419 (6)	0.0048 (5)	0.0147 (5)	0.0002 (5)

O1—C22	1.3742 (14)	C10—C11	1.4053 (19)
O1—C7	1.4347 (15)	C10—C15	1.4130 (18)
O2—C9	1.3749 (15)	C11—C12	1.370 (2)
O2—C8	1.4285 (16)	C11—H11A	0.9300
C1—C6	1.376 (2)	C12—C13	1.381 (2)
C1—C2	1.384 (2)	C12—H12A	0.9300
C1—H1A	0.9300	C13—C14	1.366 (2)
C2—C3	1.373 (3)	C13—H13A	0.9300
C2—H2A	0.9300	C14—C15	1.4027 (18)
C3—C4	1.366 (3)	C14—H14A	0.9300
C3—H3A	0.9300	C15—C16	1.4570 (19)
C4—C5	1.378 (2)	C16—C21	1.4086 (18)
C4—H4A	0.9300	C16—C17	1.4103 (18)
C5—C6	1.3882 (19)	C17—C18	1.368 (2)
C5—H5A	0.9300	C17—H17A	0.9300
C6—C7	1.5002 (18)	C18—C19	1.388 (2)
C7—C8	1.5128 (18)	C18—H18A	0.9300
C7—H7A	0.9800	C19—C20	1.3680 (18)
C8—H8A	0.9700	C19—H19A	0.9300
C8—H8B	0.9700	C20—C21	1.4074 (18)
C9—C22	1.3527 (17)	C20—H20A	0.9300
C9—C10	1.4337 (17)	C21—C22	1.4361 (17)
C22—O1—C7	112.41 (9)	C15—C10—C9	119.32 (11)
C9—O2—C8	113.33 (10)	C12—C11—C10	120.44 (14)
C6—C1—C2	120.25 (15)	C12—C11—H11A	119.8
C6—C1—H1A	119.9	C10—C11—H11A	119.8
C2—C1—H1A	119.9	C11—C12—C13	120.06 (14)
C3—C2—C1	120.32 (17)	C11—C12—H12A	120.0
C3—C2—H2A	119.8	C13—C12—H12A	120.0
C1—C2—H2A	119.8	C14—C13—C12	120.62 (14)
C4—C3—C2	119.81 (15)	C14—C13—H13A	119.7
C4—C3—H3A	120.1	C12—C13—H13A	119.7
C2—C3—H3A	120.1	C13—C14—C15	121.39 (14)
C3—C4—C5	120.33 (16)	C13—C14—H14A	119.3
C3—C4—H4A	119.8	C15—C14—H14A	119.3
C5—C4—H4A	119.8	C14—C15—C10	117.76 (12)
C4—C5—C6	120.40 (16)	C14—C15—C16	122.88 (12)
C4—C5—H5A	119.8	C10—C15—C16	119.36 (11)
C6—C5—H5A	119.8	C21—C16—C17	117.38 (12)
C1—C6—C5	118.87 (13)	C21—C16—C15	119.29 (11)
C1—C6—C7	121.44 (12)	C17—C16—C15	123.32 (12)
C5—C6—C7	119.58 (13)	C18—C17—C16	121.56 (14)
O1—C7—C6	108.98 (10)	C18—C17—H17A	119.2
O1—C7—C8	108.36 (10)	C16—C17—H17A	119.2
C6—C7—C8	111.39 (10)	C17—C18—C19	120.48 (13)
O1—C7—H7A	109.4	C17—C18—H18A	119.8
C6—C7—H7A	109.4	C19—C18—H18A	119.8
C8—C7—H7A	109.4	C20—C19—C18	119.84 (14)
O2—C8—C7	111.52 (11)	C20—C19—H19A	120.1
O2—C8—H8A	109.3	C18—C19—H19A	120.1
C7—C8—H8A	109.3	C19—C20—C21	120.61 (13)
O2—C8—H8B	109.3	C19—C20—H20A	119.7
C7—C8—H8B	109.3	C21—C20—H20A	119.7
H8A—C8—H8B	108.0	C20—C21—C16	120.07 (11)
C22—C9—O2	123.01 (11)	C20—C21—C22	120.54 (11)
C22—C9—C10	121.12 (11)	C16—C21—C22	119.33 (11)
O2—C9—C10	115.82 (11)	C9—C22—O1	122.63 (11)
C11—C10—C15	119.68 (12)	C9—C22—C21	121.26 (11)
C11—C10—C9	120.98 (12)	O1—C22—C21	116.06 (10)
C6—C1—C2—C3	0.4 (2)	C11—C10—C15—C14	−2.33 (19)
C1—C2—C3—C4	0.2 (2)	C9—C10—C15—C14	176.42 (11)
C2—C3—C4—C5	0.0 (2)	C11—C10—C15—C16	177.24 (12)
C3—C4—C5—C6	−0.9 (2)	C9—C10—C15—C16	−4.02 (18)
C2—C1—C6—C5	−1.3 (2)	C14—C15—C16—C21	179.16 (12)
C2—C1—C6—C7	175.03 (13)	C10—C15—C16—C21	−0.38 (17)
C4—C5—C6—C1	1.5 (2)	C14—C15—C16—C17	−1.50 (19)
C4—C5—C6—C7	−174.83 (13)	C10—C15—C16—C17	178.96 (12)
C22—O1—C7—C6	−171.11 (9)	C21—C16—C17—C18	−1.3 (2)
C22—O1—C7—C8	−49.75 (14)	C15—C16—C17—C18	179.35 (13)
C1—C6—C7—O1	31.63 (16)	C16—C17—C18—C19	−0.7 (2)
C5—C6—C7—O1	−152.09 (11)	C17—C18—C19—C20	1.2 (2)
C1—C6—C7—C8	−87.87 (15)	C18—C19—C20—C21	0.2 (2)
C5—C6—C7—C8	88.41 (15)	C19—C20—C21—C16	−2.18 (19)
C9—O2—C8—C7	−40.45 (16)	C19—C20—C21—C22	174.94 (12)
O1—C7—C8—O2	61.41 (15)	C17—C16—C21—C20	2.68 (18)
C6—C7—C8—O2	−178.73 (11)	C15—C16—C21—C20	−177.94 (11)
C8—O2—C9—C22	10.01 (18)	C17—C16—C21—C22	−174.49 (11)
C8—O2—C9—C10	−172.32 (11)	C15—C16—C21—C22	4.90 (17)
C22—C9—C10—C11	−177.33 (12)	O2—C9—C22—O1	0.8 (2)
O2—C9—C10—C11	4.95 (18)	C10—C9—C22—O1	−176.74 (11)
C22—C9—C10—C15	3.94 (19)	O2—C9—C22—C21	178.22 (11)
O2—C9—C10—C15	−173.77 (11)	C10—C9—C22—C21	0.67 (19)
C15—C10—C11—C12	1.4 (2)	C7—O1—C22—C9	21.05 (16)
C9—C10—C11—C12	−177.34 (13)	C7—O1—C22—C21	−156.48 (10)
C10—C11—C12—C13	0.6 (2)	C20—C21—C22—C9	177.71 (12)
C11—C12—C13—C14	−1.6 (2)	C16—C21—C22—C9	−5.14 (18)
C12—C13—C14—C15	0.6 (2)	C20—C21—C22—O1	−4.72 (17)
C13—C14—C15—C10	1.4 (2)	C16—C21—C22—O1	172.42 (10)
C13—C14—C15—C16	−178.18 (13)