3-Phenyl-1-(p-tol-yl)-1H-benzo[f]chromene benzene hemisolvate.

The title compound, C(26)H(20)O·0.5C(6)H(6), was obtained from condensation reaction of 2-naphthol, 4-methyl-benzaldehyde and phenyl-methanamine. The naphthyl ring system is orented at dihedral angles of 84.11 (1) and 19.33 (8)° with respect to the mean planes of the two benzene rings.

Related literature

For applications of Betti-type reactions, see: Wang et al. (2005 ▶). The reaction of substituted phenols and aldehydes under controlled conditions has been used to build up a compound with two chiral centers, see: Gardiner & Raston (1997 ▶); Gutsche & Nam (1998 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C26H20O·0.5C6H6

M = 387.47

Monoclinic,

a = 12.653 (3) Å

b = 5.9049 (12) Å

c = 29.974 (8) Å

β = 109.08 (3)°

V = 2116.5 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.813, T max = 1.000

14405 measured reflections

3623 independent reflections

1438 reflections with I > 2σ(I)

R int = 0.148

Refinement

R[F 2 > 2σ(F 2)] = 0.080

wR(F 2) = 0.144

S = 0.93

3623 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811001668/jh2252sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811001668/jh2252Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811001668/jh2252Isup3.cml

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

C26H20O·0.5C6H6	F(000) = 820
Mr = 387.47	Dx = 1.216 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3623 reflections
a = 12.653 (3) Å	θ = 2.6–24.8°
b = 5.9049 (12) Å	µ = 0.07 mm−1
c = 29.974 (8) Å	T = 293 K
β = 109.08 (3)°	Prism, colorless
V = 2116.5 (9) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Rigaku Mercury2 diffractometer	3623 independent reflections
Radiation source: fine-focus sealed tube	1438 reflections with I > 2σ(I)
graphite	Rint = 0.148
Detector resolution: 13.6612 pixels mm-1	θmax = 24.8°, θmin = 3.2°
CCD_Profile_fitting scans	h = −14→13
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −6→6
Tmin = 0.813, Tmax = 1.000	l = −35→35
14405 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.080	H-atom parameters constrained
wR(F2) = 0.144	w = 1/[σ2(Fo2) + (0.010P)2 + 1.9P] where P = (Fo2 + 2Fc2)/3
S = 0.93	(Δ/σ)max < 0.001
3623 reflections	Δρmax = 0.18 e Å−3
273 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0054 (6)

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	0.1992 (2)	1.0645 (5)	0.23039 (9)	0.0549 (8)
C5	−0.1441 (4)	1.0682 (8)	0.16184 (15)	0.0502 (12)
C10	−0.0792 (4)	0.8897 (8)	0.15186 (14)	0.0464 (12)
C1	0.0391 (4)	0.8852 (7)	0.17364 (14)	0.0433 (11)
C11	0.1128 (3)	0.7117 (7)	0.16231 (13)	0.0464 (12)
H11A	0.0762	0.5639	0.1601	0.056*
C12	0.1302 (3)	0.7595 (8)	0.11524 (14)	0.0452 (11)
C2	0.0853 (4)	1.0539 (8)	0.20516 (14)	0.0468 (12)
C9	−0.1366 (4)	0.7168 (8)	0.12064 (15)	0.0591 (13)
H9A	−0.0957	0.5997	0.1135	0.071*
C3	0.0233 (4)	1.2317 (7)	0.21550 (14)	0.0497 (12)
H3A	0.0589	1.3428	0.2372	0.060*
C6	−0.2621 (4)	1.0666 (9)	0.13957 (16)	0.0664 (15)
H6A	−0.3047	1.1837	0.1455	0.080*
C4	−0.0887 (4)	1.2401 (8)	0.19354 (14)	0.0557 (13)
H4A	−0.1296	1.3606	0.1994	0.067*
C8	−0.2511 (5)	0.7169 (9)	0.10062 (16)	0.0689 (15)
H8A	−0.2870	0.5981	0.0811	0.083*
C13	0.1067 (4)	0.6008 (8)	0.08004 (16)	0.0673 (15)
H13A	0.0820	0.4582	0.0854	0.081*
C17	0.1694 (4)	0.9652 (8)	0.10589 (16)	0.0619 (14)
H17A	0.1881	1.0752	0.1294	0.074*
C15	0.1555 (4)	0.8569 (10)	0.02733 (16)	0.0649 (15)
C7	−0.3138 (4)	0.8968 (10)	0.10966 (17)	0.0737 (16)
H7A	−0.3910	0.9000	0.0952	0.088*
C14	0.1188 (4)	0.6477 (10)	0.03650 (17)	0.0752 (16)
H14A	0.1020	0.5365	0.0133	0.090*
C18	0.1597 (4)	0.9155 (10)	−0.02193 (15)	0.103 (2)
H18A	0.1856	1.0682	−0.0220	0.155*
H18B	0.0862	0.9012	−0.0446	0.155*
H18C	0.2098	0.8137	−0.0300	0.155*
C16	0.1819 (4)	1.0139 (9)	0.06301 (18)	0.0712 (16)
H16A	0.2086	1.1554	0.0582	0.085*
C27	0.5726 (5)	1.0641 (15)	0.4766 (2)	0.097 (2)
H27A	0.6217	1.1072	0.4609	0.117*
C28	0.5207 (6)	0.8584 (14)	0.4683 (2)	0.096 (2)
H28A	0.5347	0.7606	0.4466	0.115*
C29	0.4494 (5)	0.7940 (10)	0.4912 (3)	0.0953 (19)
H29A	0.4151	0.6528	0.4850	0.114*
C25	0.4963 (4)	1.0693 (9)	0.33788 (16)	0.0753 (16)
H25A	0.5136	1.1949	0.3577	0.090*
C26	0.3953 (4)	1.0623 (9)	0.30149 (15)	0.0639 (14)
H26A	0.3452	1.1819	0.2973	0.077*
C21	0.3688 (4)	0.8798 (8)	0.27155 (15)	0.0491 (12)
C23	0.5458 (4)	0.7128 (9)	0.31572 (17)	0.0740 (16)
H23A	0.5962	0.5933	0.3204	0.089*
C24	0.5710 (4)	0.8955 (10)	0.34533 (16)	0.0727 (16)
H24A	0.6381	0.9011	0.3702	0.087*
C22	0.4449 (4)	0.7045 (8)	0.27852 (15)	0.0615 (14)
H22A	0.4288	0.5804	0.2583	0.074*
C20	0.2610 (4)	0.8690 (8)	0.23220 (14)	0.0444 (11)
C19	0.2214 (4)	0.7014 (8)	0.20194 (14)	0.0503 (12)
H19A	0.2636	0.5696	0.2056	0.060*

	U11	U22	U33	U12	U13	U23
O1	0.045 (2)	0.052 (2)	0.063 (2)	0.0056 (18)	0.0123 (16)	−0.0046 (16)
C5	0.052 (4)	0.057 (4)	0.044 (3)	0.002 (3)	0.019 (3)	0.012 (2)
C10	0.054 (3)	0.050 (3)	0.037 (3)	−0.004 (3)	0.017 (2)	0.006 (2)
C1	0.051 (3)	0.041 (3)	0.041 (3)	0.005 (2)	0.020 (2)	0.002 (2)
C11	0.054 (3)	0.045 (3)	0.042 (3)	−0.003 (2)	0.019 (2)	−0.001 (2)
C12	0.045 (3)	0.046 (3)	0.045 (3)	0.002 (2)	0.015 (2)	−0.002 (2)
C2	0.051 (3)	0.050 (3)	0.044 (3)	0.005 (3)	0.023 (3)	0.004 (2)
C9	0.051 (4)	0.072 (4)	0.053 (3)	0.000 (3)	0.016 (3)	0.009 (3)
C3	0.058 (3)	0.047 (3)	0.045 (3)	0.005 (3)	0.017 (2)	0.004 (2)
C6	0.053 (4)	0.087 (4)	0.058 (3)	0.017 (3)	0.016 (3)	0.015 (3)
C4	0.064 (4)	0.058 (4)	0.048 (3)	0.013 (3)	0.023 (3)	0.003 (3)
C8	0.069 (4)	0.071 (4)	0.061 (3)	−0.008 (3)	0.013 (3)	0.010 (3)
C13	0.087 (4)	0.060 (4)	0.063 (3)	−0.004 (3)	0.036 (3)	−0.010 (3)
C17	0.081 (4)	0.055 (4)	0.054 (3)	−0.011 (3)	0.028 (3)	−0.006 (3)
C15	0.059 (4)	0.093 (5)	0.047 (3)	0.013 (3)	0.024 (3)	0.005 (3)
C7	0.057 (4)	0.094 (5)	0.065 (4)	−0.003 (4)	0.013 (3)	0.015 (3)
C14	0.081 (4)	0.092 (5)	0.053 (3)	−0.009 (3)	0.022 (3)	−0.024 (3)
C18	0.101 (5)	0.157 (6)	0.061 (4)	0.027 (4)	0.040 (3)	0.025 (4)
C16	0.088 (4)	0.068 (4)	0.069 (4)	0.002 (3)	0.041 (3)	0.011 (3)
C27	0.082 (5)	0.116 (6)	0.093 (5)	−0.011 (5)	0.027 (4)	0.016 (4)
C28	0.080 (5)	0.112 (7)	0.093 (5)	−0.003 (4)	0.026 (4)	−0.014 (4)
C29	0.082 (5)	0.082 (5)	0.111 (6)	−0.018 (4)	0.017 (4)	−0.002 (4)
C25	0.075 (4)	0.085 (5)	0.059 (4)	0.001 (4)	0.012 (3)	−0.012 (3)
C26	0.060 (4)	0.070 (4)	0.053 (3)	0.014 (3)	0.007 (3)	−0.006 (3)
C21	0.049 (3)	0.056 (3)	0.047 (3)	0.009 (3)	0.023 (2)	0.007 (3)
C23	0.059 (4)	0.095 (5)	0.063 (4)	0.020 (3)	0.012 (3)	0.003 (3)
C24	0.054 (4)	0.110 (5)	0.047 (3)	0.003 (4)	0.007 (3)	−0.004 (3)
C22	0.054 (4)	0.070 (4)	0.058 (3)	0.008 (3)	0.015 (3)	−0.003 (3)
C20	0.039 (3)	0.051 (3)	0.048 (3)	0.005 (3)	0.019 (2)	0.006 (2)
C19	0.058 (3)	0.048 (3)	0.042 (3)	0.007 (3)	0.013 (2)	0.002 (2)

O1—C20	1.386 (4)	C15—C14	1.379 (6)
O1—C2	1.392 (5)	C15—C18	1.534 (6)
C5—C4	1.410 (5)	C7—H7A	0.9300
C5—C6	1.422 (6)	C14—H14A	0.9300
C5—C10	1.427 (5)	C18—H18A	0.9600
C10—C9	1.415 (5)	C18—H18B	0.9600
C10—C1	1.424 (5)	C18—H18C	0.9600
C1—C2	1.366 (5)	C16—H16A	0.9300
C1—C11	1.498 (5)	C27—C28	1.364 (7)
C11—C19	1.495 (5)	C27—C29i	1.374 (7)
C11—C12	1.523 (5)	C27—H27A	0.9300
C11—H11A	0.9800	C28—C29	1.353 (7)
C12—C13	1.369 (5)	C28—H28A	0.9300
C12—C17	1.375 (5)	C29—C27i	1.374 (7)
C2—C3	1.405 (5)	C29—H29A	0.9300
C9—C8	1.376 (6)	C25—C24	1.363 (6)
C9—H9A	0.9300	C25—C26	1.383 (5)
C3—C4	1.355 (5)	C25—H25A	0.9300
C3—H3A	0.9300	C26—C21	1.372 (5)
C6—C7	1.361 (6)	C26—H26A	0.9300
C6—H6A	0.9300	C21—C22	1.383 (5)
C4—H4A	0.9300	C21—C20	1.484 (5)
C8—C7	1.404 (6)	C23—C24	1.367 (6)
C8—H8A	0.9300	C23—C22	1.394 (5)
C13—C14	1.391 (6)	C23—H23A	0.9300
C13—H13A	0.9300	C24—H24A	0.9300
C17—C16	1.376 (5)	C22—H22A	0.9300
C17—H17A	0.9300	C20—C19	1.325 (5)
C15—C16	1.372 (6)	C19—H19A	0.9300
C20—O1—C2	117.0 (3)	C6—C7—H7A	119.9
C4—C5—C6	122.4 (5)	C8—C7—H7A	119.9
C4—C5—C10	118.6 (4)	C15—C14—C13	120.9 (5)
C6—C5—C10	119.0 (5)	C15—C14—H14A	119.6
C9—C10—C1	121.6 (4)	C13—C14—H14A	119.6
C9—C10—C5	117.8 (4)	C15—C18—H18A	109.5
C1—C10—C5	120.6 (4)	C15—C18—H18B	109.5
C2—C1—C10	116.9 (4)	H18A—C18—H18B	109.5
C2—C1—C11	119.8 (4)	C15—C18—H18C	109.5
C10—C1—C11	123.3 (4)	H18A—C18—H18C	109.5
C19—C11—C1	109.1 (3)	H18B—C18—H18C	109.5
C19—C11—C12	111.7 (3)	C15—C16—C17	120.9 (5)
C1—C11—C12	111.9 (3)	C15—C16—H16A	119.5
C19—C11—H11A	108.0	C17—C16—H16A	119.5
C1—C11—H11A	108.0	C28—C27—C29i	118.3 (6)
C12—C11—H11A	108.0	C28—C27—H27A	120.8
C13—C12—C17	116.7 (4)	C29i—C27—H27A	120.8
C13—C12—C11	121.7 (4)	C29—C28—C27	121.3 (6)
C17—C12—C11	121.6 (4)	C29—C28—H28A	119.4
C1—C2—O1	122.8 (4)	C27—C28—H28A	119.4
C1—C2—C3	123.6 (4)	C28—C29—C27i	120.4 (6)
O1—C2—C3	113.6 (4)	C28—C29—H29A	119.8
C8—C9—C10	121.9 (5)	C27i—C29—H29A	119.8
C8—C9—H9A	119.1	C24—C25—C26	121.3 (5)
C10—C9—H9A	119.1	C24—C25—H25A	119.4
C4—C3—C2	119.4 (4)	C26—C25—H25A	119.4
C4—C3—H3A	120.3	C21—C26—C25	120.3 (5)
C2—C3—H3A	120.3	C21—C26—H26A	119.8
C7—C6—C5	121.3 (5)	C25—C26—H26A	119.8
C7—C6—H6A	119.4	C26—C21—C22	118.7 (4)
C5—C6—H6A	119.4	C26—C21—C20	121.2 (4)
C3—C4—C5	120.8 (4)	C22—C21—C20	120.1 (4)
C3—C4—H4A	119.6	C24—C23—C22	120.3 (5)
C5—C4—H4A	119.6	C24—C23—H23A	119.8
C9—C8—C7	119.8 (5)	C22—C23—H23A	119.8
C9—C8—H8A	120.1	C25—C24—C23	119.1 (5)
C7—C8—H8A	120.1	C25—C24—H24A	120.5
C12—C13—C14	121.6 (5)	C23—C24—H24A	120.5
C12—C13—H13A	119.2	C21—C22—C23	120.3 (5)
C14—C13—H13A	119.2	C21—C22—H22A	119.8
C12—C17—C16	122.3 (4)	C23—C22—H22A	119.8
C12—C17—H17A	118.8	C19—C20—O1	120.9 (4)
C16—C17—H17A	118.8	C19—C20—C21	128.3 (4)
C16—C15—C14	117.5 (4)	O1—C20—C21	110.8 (4)
C16—C15—C18	121.5 (5)	C20—C19—C11	123.8 (4)
C14—C15—C18	120.9 (5)	C20—C19—H19A	118.1
C6—C7—C8	120.3 (5)	C11—C19—H19A	118.1

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26A···O1	0.93	2.34	2.692 (6)	102.