3,3-Bis(3,5-dimethyl­phen­yl)-3H-benzo[f]chromene

In the title mol­ecule, C₂₉H₂₆O, the two methyl substituents on the benzene rings are sterically hindered and influence the structure of the mol­ecule and its photochemical properties. The dihedral angle between the two benzene ring planes is 80.2 (1)°.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.049
• wR factor = 0.146
• Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT048_ALERT_1_C MoietyFormula Not Given ........................          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C10     ..       5.30 su

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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

---

Computing details

Data collection: APEX2, (Bruker 2004); cell refinement: APEX2; data reduction: SAINT, (Bruker 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker 2004); software used to prepare material for publication: SHELXTL.

(VI)

Crystal data

C29H26O	F(000) = 832
Mr = 390.50	Dx = 1.174 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.5290 (8) Å	Cell parameters from 2527 reflections
b = 11.3445 (8) Å	θ = 2.5–21.8°
c = 16.9415 (12) Å	µ = 0.07 mm^−1
β = 94.124 (1)°	T = 291 K
V = 2210.1 (3) Å^3	Block, colourless
Z = 4	0.35 × 0.18 × 0.09 mm

Data collection

Bruker ApexII CCD area-detector diffractometer	5053 independent reflections
Radiation source: fine-focus sealed tube	3024 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick,1996)	h = −14→14
Tmin = 0.976, Tmax = 0.994	k = −14→14
13103 measured reflections	l = −12→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.146	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.065P)^2 + 0.2364P] where P = (Fo^2 + 2Fc^2)/3
5053 reflections	(Δ/σ)max < 0.001
275 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

Experimental. IR spectra were obtained on a Shimadzu-IR 435 spectrometer. ¹H-NMR spectra were recorded on a Bruker AC–P200 spectrometer with TMS as the internal standard. Elemental analysis was performed on a Yanaco MT-3 instrument. Melting points were determined with a model Yanaco MP-500 apparatus and uncorrected.

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.

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

	x	y	z	Uiso*/Ueq
O1	−0.05573 (9)	0.52133 (10)	0.22760 (7)	0.0499 (3)
C1	0.02356 (14)	0.70141 (14)	0.28369 (10)	0.0471 (4)
C2	0.00158 (15)	0.81414 (15)	0.31856 (10)	0.0501 (4)
C3	0.09189 (18)	0.88901 (16)	0.34917 (12)	0.0638 (5)
H3	0.1690	0.8664	0.3461	0.077*
C4	0.0671 (2)	0.99450 (19)	0.38335 (14)	0.0786 (6)
H4	0.1277	1.0429	0.4029	0.094*
C5	−0.0481 (2)	1.03080 (19)	0.38940 (13)	0.0786 (6)
H5	−0.0636	1.1029	0.4125	0.094*
C6	−0.13680 (19)	0.96044 (17)	0.36139 (12)	0.0664 (5)
H6	−0.2131	0.9844	0.3660	0.080*
C7	−0.11483 (15)	0.85058 (15)	0.32505 (10)	0.0526 (4)
C8	−0.20620 (16)	0.77609 (17)	0.29728 (11)	0.0599 (5)
H8	−0.2827	0.8009	0.3001	0.072*
C9	−0.18454 (15)	0.66785 (17)	0.26615 (11)	0.0571 (5)
H9	−0.2459	0.6190	0.2486	0.069*
C10	−0.07002 (14)	0.63104 (15)	0.26090 (10)	0.0469 (4)
C11	0.13810 (14)	0.65912 (16)	0.26738 (11)	0.0548 (5)
H11	0.2014	0.7102	0.2712	0.066*
C12	0.15246 (15)	0.54795 (16)	0.24703 (11)	0.0547 (5)
H12	0.2246	0.5232	0.2320	0.066*
C13	0.05385 (13)	0.46006 (15)	0.24772 (10)	0.0463 (4)
C14	0.05931 (13)	0.36723 (15)	0.18275 (10)	0.0473 (4)
C15	0.08758 (15)	0.40152 (17)	0.10790 (11)	0.0568 (5)
H15	0.1049	0.4803	0.0990	0.068*
C16	0.09075 (16)	0.32194 (19)	0.04607 (10)	0.0601 (5)
C17	0.06515 (15)	0.20493 (18)	0.06114 (11)	0.0603 (5)
H17	0.0681	0.1502	0.0205	0.072*
C18	0.03534 (15)	0.16678 (17)	0.13457 (11)	0.0553 (5)
C19	0.03291 (14)	0.24949 (16)	0.19521 (10)	0.0508 (4)
H19	0.0132	0.2254	0.2450	0.061*
C20	0.1227 (2)	0.3622 (2)	−0.03457 (12)	0.0925 (8)
H20A	0.2052	0.3558	−0.0377	0.139*
H20B	0.0994	0.4428	−0.0427	0.139*
H20C	0.0837	0.3137	−0.0746	0.139*
C21	0.0056 (2)	0.03991 (19)	0.14847 (14)	0.0859 (7)
H21A	−0.0731	0.0251	0.1286	0.129*
H21B	0.0136	0.0235	0.2042	0.129*
H21C	0.0573	−0.0099	0.1216	0.129*
C22	0.05351 (14)	0.40690 (14)	0.33044 (9)	0.0439 (4)
C23	0.15580 (15)	0.35773 (16)	0.36443 (10)	0.0527 (4)
H23	0.2215	0.3562	0.3357	0.063*
C24	0.16198 (16)	0.31105 (17)	0.44007 (11)	0.0593 (5)
C25	0.06333 (17)	0.31587 (16)	0.48215 (11)	0.0602 (5)
H25	0.0669	0.2861	0.5334	0.072*
C26	−0.03954 (16)	0.36308 (15)	0.45067 (10)	0.0520 (4)
C27	−0.04380 (14)	0.40774 (14)	0.37397 (10)	0.0478 (4)
H27	−0.1132	0.4387	0.3515	0.057*
C28	−0.14498 (18)	0.36910 (19)	0.49831 (13)	0.0733 (6)
H28A	−0.1582	0.2933	0.5212	0.110*
H28B	−0.2117	0.3913	0.4644	0.110*
H28C	−0.1321	0.4265	0.5397	0.110*
C29	0.2750 (2)	0.2597 (2)	0.47629 (15)	0.0917 (7)
H29A	0.3097	0.3137	0.5147	0.138*
H29B	0.3272	0.2466	0.4355	0.138*
H29C	0.2595	0.1862	0.5016	0.138*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0460 (6)	0.0500 (7)	0.0535 (7)	0.0046 (5)	0.0024 (5)	−0.0049 (6)
C1	0.0486 (9)	0.0466 (10)	0.0460 (9)	−0.0020 (7)	0.0041 (8)	0.0073 (8)
C2	0.0592 (10)	0.0445 (10)	0.0467 (10)	−0.0009 (8)	0.0050 (8)	0.0103 (8)
C3	0.0706 (12)	0.0522 (12)	0.0686 (13)	−0.0117 (9)	0.0046 (10)	0.0054 (10)
C4	0.0965 (17)	0.0574 (13)	0.0816 (16)	−0.0184 (12)	0.0034 (13)	−0.0055 (11)
C5	0.1078 (18)	0.0524 (13)	0.0753 (15)	−0.0008 (12)	0.0057 (13)	−0.0086 (11)
C6	0.0858 (14)	0.0528 (12)	0.0610 (12)	0.0136 (10)	0.0082 (11)	0.0021 (10)
C7	0.0631 (11)	0.0469 (10)	0.0476 (10)	0.0054 (8)	0.0027 (9)	0.0062 (8)
C8	0.0508 (10)	0.0636 (12)	0.0649 (12)	0.0143 (9)	0.0023 (9)	−0.0026 (10)
C9	0.0468 (10)	0.0617 (12)	0.0619 (12)	0.0009 (8)	−0.0023 (8)	−0.0068 (9)
C10	0.0484 (9)	0.0485 (10)	0.0443 (9)	0.0057 (7)	0.0061 (7)	0.0031 (8)
C11	0.0472 (10)	0.0544 (11)	0.0639 (12)	−0.0046 (8)	0.0106 (8)	0.0067 (9)
C12	0.0464 (10)	0.0585 (12)	0.0605 (12)	0.0008 (8)	0.0129 (8)	0.0037 (9)
C13	0.0408 (9)	0.0502 (10)	0.0483 (10)	0.0070 (7)	0.0055 (7)	−0.0006 (8)
C14	0.0434 (9)	0.0555 (11)	0.0436 (9)	0.0079 (7)	0.0063 (7)	0.0014 (8)
C15	0.0579 (11)	0.0612 (12)	0.0526 (11)	0.0125 (8)	0.0127 (9)	0.0100 (9)
C16	0.0576 (11)	0.0799 (14)	0.0435 (10)	0.0212 (10)	0.0086 (8)	0.0035 (10)
C17	0.0594 (11)	0.0766 (14)	0.0446 (10)	0.0181 (10)	0.0015 (9)	−0.0133 (10)
C18	0.0577 (10)	0.0599 (11)	0.0481 (10)	0.0066 (8)	0.0017 (8)	−0.0077 (9)
C19	0.0537 (10)	0.0579 (11)	0.0412 (9)	0.0035 (8)	0.0063 (8)	−0.0009 (8)
C20	0.1180 (19)	0.111 (2)	0.0521 (12)	0.0354 (15)	0.0294 (13)	0.0159 (13)
C21	0.1142 (19)	0.0673 (15)	0.0762 (15)	−0.0059 (13)	0.0060 (14)	−0.0164 (12)
C22	0.0473 (9)	0.0424 (9)	0.0422 (9)	−0.0013 (7)	0.0045 (7)	−0.0065 (7)
C23	0.0501 (10)	0.0587 (11)	0.0492 (10)	0.0039 (8)	0.0036 (8)	−0.0071 (9)
C24	0.0652 (12)	0.0565 (11)	0.0549 (11)	0.0018 (9)	−0.0060 (9)	−0.0014 (9)
C25	0.0778 (13)	0.0564 (11)	0.0460 (10)	−0.0079 (10)	0.0016 (10)	0.0030 (9)
C26	0.0629 (11)	0.0433 (9)	0.0509 (10)	−0.0118 (8)	0.0125 (9)	−0.0056 (8)
C27	0.0484 (9)	0.0453 (9)	0.0502 (10)	−0.0022 (7)	0.0062 (8)	−0.0042 (8)
C28	0.0821 (14)	0.0736 (14)	0.0678 (13)	−0.0191 (11)	0.0306 (11)	−0.0039 (11)
C29	0.0828 (15)	0.1089 (19)	0.0803 (16)	0.0183 (14)	−0.0169 (13)	0.0139 (14)

Geometric parameters (Å, º)

O1—C10	1.381 (2)	C16—C17	1.388 (3)
O1—C13	1.4607 (19)	C16—C20	1.511 (3)
C1—C10	1.375 (2)	C17—C18	1.384 (3)
C1—C2	1.439 (2)	C17—H17	0.9300
C1—C11	1.450 (2)	C18—C19	1.393 (2)
C2—C3	1.413 (2)	C18—C21	1.502 (3)
C2—C7	1.416 (2)	C19—H19	0.9300
C3—C4	1.369 (3)	C20—H20A	0.9600
C3—H3	0.9300	C20—H20B	0.9600
C4—C5	1.401 (3)	C20—H20C	0.9600
C4—H4	0.9300	C21—H21A	0.9600
C5—C6	1.356 (3)	C21—H21B	0.9600
C5—H5	0.9300	C21—H21C	0.9600
C6—C7	1.421 (3)	C22—C27	1.386 (2)
C6—H6	0.9300	C22—C23	1.391 (2)
C7—C8	1.405 (3)	C23—C24	1.384 (2)
C8—C9	1.366 (2)	C23—H23	0.9300
C8—H8	0.9300	C24—C25	1.386 (3)
C9—C10	1.394 (2)	C24—C29	1.516 (3)
C9—H9	0.9300	C25—C26	1.374 (3)
C11—C12	1.321 (2)	C25—H25	0.9300
C11—H11	0.9300	C26—C27	1.392 (2)
C12—C13	1.513 (2)	C26—C28	1.508 (2)
C12—H12	0.9300	C27—H27	0.9300
C13—C22	1.526 (2)	C28—H28A	0.9600
C13—C14	1.528 (2)	C28—H28B	0.9600
C14—C15	1.387 (2)	C28—H28C	0.9600
C14—C19	1.389 (2)	C29—H29A	0.9600
C15—C16	1.385 (3)	C29—H29B	0.9600
C15—H15	0.9300	C29—H29C	0.9600
C10—O1—C13	117.39 (12)	C18—C17—C16	122.32 (17)
C10—C1—C2	118.27 (15)	C18—C17—H17	118.8
C10—C1—C11	117.48 (15)	C16—C17—H17	118.8
C2—C1—C11	124.19 (15)	C17—C18—C19	118.15 (18)
C3—C2—C7	118.26 (17)	C17—C18—C21	120.99 (18)
C3—C2—C1	122.55 (16)	C19—C18—C21	120.86 (18)
C7—C2—C1	119.16 (15)	C14—C19—C18	121.28 (16)
C4—C3—C2	120.7 (2)	C14—C19—H19	119.4
C4—C3—H3	119.7	C18—C19—H19	119.4
C2—C3—H3	119.7	C16—C20—H20A	109.5
C3—C4—C5	121.1 (2)	C16—C20—H20B	109.5
C3—C4—H4	119.5	H20A—C20—H20B	109.5
C5—C4—H4	119.5	C16—C20—H20C	109.5
C6—C5—C4	119.8 (2)	H20A—C20—H20C	109.5
C6—C5—H5	120.1	H20B—C20—H20C	109.5
C4—C5—H5	120.1	C18—C21—H21A	109.5
C5—C6—C7	121.0 (2)	C18—C21—H21B	109.5
C5—C6—H6	119.5	H21A—C21—H21B	109.5
C7—C6—H6	119.5	C18—C21—H21C	109.5
C8—C7—C2	119.36 (16)	H21A—C21—H21C	109.5
C8—C7—C6	121.33 (17)	H21B—C21—H21C	109.5
C2—C7—C6	119.29 (17)	C27—C22—C23	118.49 (15)
C9—C8—C7	121.08 (17)	C27—C22—C13	122.79 (14)
C9—C8—H8	119.5	C23—C22—C13	118.71 (14)
C7—C8—H8	119.5	C24—C23—C22	121.49 (16)
C8—C9—C10	119.61 (17)	C24—C23—H23	119.3
C8—C9—H9	120.2	C22—C23—H23	119.3
C10—C9—H9	120.2	C23—C24—C25	118.15 (17)
C1—C10—O1	121.58 (14)	C23—C24—C29	120.50 (18)
C1—C10—C9	122.41 (16)	C25—C24—C29	121.33 (18)
O1—C10—C9	115.94 (15)	C26—C25—C24	122.22 (17)
C12—C11—C1	119.90 (16)	C26—C25—H25	118.9
C12—C11—H11	120.1	C24—C25—H25	118.9
C1—C11—H11	120.1	C25—C26—C27	118.41 (16)
C11—C12—C13	121.26 (15)	C25—C26—C28	121.10 (17)
C11—C12—H12	119.4	C27—C26—C28	120.49 (17)
C13—C12—H12	119.4	C22—C27—C26	121.23 (16)
O1—C13—C12	108.81 (14)	C22—C27—H27	119.4
O1—C13—C22	110.06 (12)	C26—C27—H27	119.4
C12—C13—C22	108.61 (14)	C26—C28—H28A	109.5
O1—C13—C14	103.87 (12)	C26—C28—H28B	109.5
C12—C13—C14	112.26 (13)	H28A—C28—H28B	109.5
C22—C13—C14	113.09 (14)	C26—C28—H28C	109.5
C15—C14—C19	118.48 (16)	H28A—C28—H28C	109.5
C15—C14—C13	119.32 (16)	H28B—C28—H28C	109.5
C19—C14—C13	122.16 (15)	C24—C29—H29A	109.5
C16—C15—C14	121.95 (18)	C24—C29—H29B	109.5
C16—C15—H15	119.0	H29A—C29—H29B	109.5
C14—C15—H15	119.0	C24—C29—H29C	109.5
C15—C16—C17	117.82 (17)	H29A—C29—H29C	109.5
C15—C16—C20	120.5 (2)	H29B—C29—H29C	109.5
C17—C16—C20	121.64 (19)
C10—C1—C2—C3	175.23 (16)	C12—C13—C14—C15	−41.6 (2)
C11—C1—C2—C3	−7.9 (3)	C22—C13—C14—C15	−164.93 (14)
C10—C1—C2—C7	−2.7 (2)	O1—C13—C14—C19	−101.94 (17)
C11—C1—C2—C7	174.23 (16)	C12—C13—C14—C19	140.68 (16)
C7—C2—C3—C4	−0.7 (3)	C22—C13—C14—C19	17.4 (2)
C1—C2—C3—C4	−178.63 (18)	C19—C14—C15—C16	−0.4 (2)
C2—C3—C4—C5	0.4 (3)	C13—C14—C15—C16	−178.19 (15)
C3—C4—C5—C6	0.3 (3)	C14—C15—C16—C17	−0.3 (3)
C4—C5—C6—C7	−0.7 (3)	C14—C15—C16—C20	−179.60 (17)
C3—C2—C7—C8	−178.05 (16)	C15—C16—C17—C18	1.0 (3)
C1—C2—C7—C8	−0.1 (2)	C20—C16—C17—C18	−179.74 (18)
C3—C2—C7—C6	0.3 (2)	C16—C17—C18—C19	−0.9 (3)
C1—C2—C7—C6	178.32 (15)	C16—C17—C18—C21	178.66 (18)
C5—C6—C7—C8	178.72 (19)	C15—C14—C19—C18	0.5 (2)
C5—C6—C7—C2	0.4 (3)	C13—C14—C19—C18	178.23 (15)
C2—C7—C8—C9	1.8 (3)	C17—C18—C19—C14	0.1 (3)
C6—C7—C8—C9	−176.53 (17)	C21—C18—C19—C14	−179.44 (18)
C7—C8—C9—C10	−0.8 (3)	O1—C13—C22—C27	6.6 (2)
C2—C1—C10—O1	−179.47 (14)	C12—C13—C22—C27	125.63 (16)
C11—C1—C10—O1	3.4 (2)	C14—C13—C22—C27	−109.06 (17)
C2—C1—C10—C9	3.8 (3)	O1—C13—C22—C23	−171.95 (14)
C11—C1—C10—C9	−173.28 (16)	C12—C13—C22—C23	−52.9 (2)
C13—O1—C10—C1	26.3 (2)	C14—C13—C22—C23	72.38 (19)
C13—O1—C10—C9	−156.81 (15)	C27—C22—C23—C24	−0.4 (3)
C8—C9—C10—C1	−2.1 (3)	C13—C22—C23—C24	178.21 (16)
C8—C9—C10—O1	−179.03 (15)	C22—C23—C24—C25	−0.9 (3)
C10—C1—C11—C12	−13.8 (3)	C22—C23—C24—C29	−179.05 (18)
C2—C1—C11—C12	169.33 (17)	C23—C24—C25—C26	1.2 (3)
C1—C11—C12—C13	−5.8 (3)	C29—C24—C25—C26	179.38 (19)
C10—O1—C13—C12	−41.72 (18)	C24—C25—C26—C27	−0.2 (3)
C10—O1—C13—C22	77.18 (17)	C24—C25—C26—C28	−178.93 (17)
C10—O1—C13—C14	−161.47 (13)	C23—C22—C27—C26	1.4 (2)
C11—C12—C13—O1	32.4 (2)	C13—C22—C27—C26	−177.12 (15)
C11—C12—C13—C22	−87.4 (2)	C25—C26—C27—C22	−1.1 (2)
C11—C12—C13—C14	146.79 (17)	C28—C26—C27—C22	177.57 (15)
O1—C13—C14—C15	75.78 (17)