2-Methyl-4-phenyl-2-(trimethyl­silyl­oxy)-3,4-dihydro-2H,5H-pyrano[3,2-c][1]benzopyran-5-one

In the title compound, C₂₂H₂₄O₄Si, the coumarin system is essentially planar and the pyran ring adopts a half-chair conformation. There are inter­molecular C—H...O and C—H...π inter­actions in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.054
• wR factor = 0.151
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.117
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.53 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.07 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         Si
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21    ..  CGA     ..       2.96 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

2-methyl-4-phenyl-2-(trimethylsilyloxy)-3,4-dihydro-2H,5H-pyrano [3,2-c][1]benzopyran-5-one

Crystal data

C22H24O4Si	F(000) = 808
Mr = 380.50	Dx = 1.227 Mg m^−3
Monoclinic, P21/n	Melting point: 418.2 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.038 (2) Å	Cell parameters from 25 reflections
b = 12.396 (3) Å	θ = 10–13°
c = 16.853 (3) Å	µ = 0.14 mm^−1
β = 100.74 (3)°	T = 293 K
V = 2060.3 (8) Å^3	Block, colourless
Z = 4	0.40 × 0.31 × 0.28 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	2297 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.117
Graphite monochromator	θmax = 26.0°, θmin = 2.1°
ω/2θ scans	h = 0→12
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995)	k = 0→15
Tmin = 0.931, Tmax = 0.962	l = −20→20
4268 measured reflections	3 standard reflections every 200 reflections
4029 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.054	H-atom parameters constrained
wR(F^2) = 0.151	w = 1/[σ^2(Fo^2) + (0.05P)^2 + 1P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
4029 reflections	Δρmax = 0.19 e Å^−3
245 parameters	Δρmin = −0.27 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0157 (13)

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.

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

	x	y	z	Uiso*/Ueq
Si	0.31523 (9)	0.26530 (8)	0.07053 (5)	0.0586 (3)
O1	0.44947 (18)	0.24306 (16)	0.14167 (11)	0.0515 (5)
O2	0.6160 (2)	0.17376 (15)	0.07717 (12)	0.0543 (5)
O3	0.87720 (19)	0.41315 (17)	0.03307 (12)	0.0576 (6)
O4	0.8915 (2)	0.4807 (2)	0.15477 (14)	0.0740 (7)
C1	0.2134 (4)	0.3587 (3)	0.1192 (2)	0.0897 (12)
H1A	0.1882	0.3242	0.1652	0.135*
H1B	0.1331	0.3784	0.0815	0.135*
H1C	0.2656	0.4222	0.1363	0.135*
C2	0.2167 (4)	0.1409 (3)	0.0392 (2)	0.0847 (12)
H2A	0.1895	0.1086	0.0854	0.127*
H2B	0.2719	0.0910	0.0161	0.127*
H2C	0.1377	0.1588	−0.0002	0.127*
C3	0.3651 (4)	0.3281 (4)	−0.0189 (2)	0.1125 (18)
H3A	0.4159	0.3926	−0.0030	0.169*
H3B	0.2853	0.3458	−0.0577	0.169*
H3C	0.4199	0.2786	−0.0426	0.169*
C4	0.5148 (4)	0.0556 (2)	0.1578 (2)	0.0699 (10)
H4A	0.4479	0.0374	0.1113	0.105*
H4B	0.4768	0.0471	0.2057	0.105*
H4C	0.5918	0.0088	0.1607	0.105*
C5	0.5593 (3)	0.1721 (2)	0.15128 (17)	0.0517 (7)
C6	0.6649 (3)	0.2082 (2)	0.22184 (17)	0.0509 (7)
H6A	0.7393	0.1570	0.2298	0.061*
H6B	0.6255	0.2080	0.2702	0.061*
C7	0.7206 (3)	0.3216 (2)	0.21002 (16)	0.0460 (7)
H7	0.8081	0.3264	0.2470	0.055*
C8	0.7515 (3)	0.3273 (2)	0.12620 (16)	0.0443 (7)
C9	0.7027 (3)	0.2544 (2)	0.06872 (16)	0.0449 (7)
C10	0.7445 (3)	0.2541 (2)	−0.00927 (16)	0.0475 (7)
C11	0.7039 (4)	0.1784 (3)	−0.06942 (19)	0.0660 (9)
H11	0.6436	0.1243	−0.0614	0.079*
C12	0.7515 (4)	0.1821 (3)	−0.1405 (2)	0.0786 (11)
H12	0.7237	0.1308	−0.1804	0.094*
C13	0.8408 (4)	0.2624 (3)	−0.1525 (2)	0.0712 (10)
H13	0.8740	0.2639	−0.2004	0.085*
C14	0.8817 (3)	0.3398 (3)	−0.09525 (19)	0.0610 (9)
H14	0.9406	0.3945	−0.1042	0.073*
C15	0.8331 (3)	0.3348 (2)	−0.02364 (17)	0.0493 (7)
C16	0.8428 (3)	0.4108 (3)	0.10861 (18)	0.0537 (8)
C17	0.6348 (3)	0.4134 (2)	0.23277 (16)	0.0464 (7)
C18	0.6242 (4)	0.4280 (3)	0.31231 (19)	0.0669 (9)
H18	0.6691	0.3808	0.3512	0.080*
C19	0.5485 (4)	0.5109 (3)	0.3356 (2)	0.0858 (12)
H19	0.5425	0.5187	0.3897	0.103*
C20	0.4825 (4)	0.5818 (3)	0.2799 (2)	0.0781 (11)
H20	0.4314	0.6376	0.2958	0.094*
C21	0.4921 (3)	0.5698 (3)	0.2003 (2)	0.0637 (9)
H21	0.4477	0.6179	0.1619	0.076*
C22	0.5677 (3)	0.4865 (2)	0.17707 (17)	0.0517 (8)
H22	0.5738	0.4793	0.1229	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si	0.0489 (5)	0.0746 (7)	0.0509 (5)	−0.0057 (5)	0.0056 (4)	0.0192 (5)
O1	0.0482 (11)	0.0537 (12)	0.0513 (11)	−0.0008 (10)	0.0064 (9)	0.0108 (10)
O2	0.0613 (13)	0.0456 (12)	0.0584 (12)	−0.0105 (10)	0.0173 (10)	−0.0013 (10)
O3	0.0520 (12)	0.0655 (14)	0.0598 (13)	−0.0170 (11)	0.0221 (10)	−0.0103 (11)
O4	0.0707 (15)	0.0843 (17)	0.0724 (15)	−0.0348 (14)	0.0271 (12)	−0.0249 (14)
C1	0.061 (2)	0.093 (3)	0.110 (3)	0.010 (2)	0.003 (2)	0.009 (3)
C2	0.073 (2)	0.104 (3)	0.071 (2)	−0.015 (2)	−0.0019 (19)	−0.005 (2)
C3	0.076 (3)	0.176 (5)	0.083 (3)	−0.006 (3)	0.009 (2)	0.080 (3)
C4	0.080 (2)	0.0482 (19)	0.078 (2)	−0.0116 (17)	0.0056 (19)	0.0190 (17)
C5	0.0545 (18)	0.0500 (18)	0.0515 (17)	0.0001 (15)	0.0126 (14)	0.0177 (14)
C6	0.0500 (17)	0.0542 (19)	0.0472 (16)	0.0050 (14)	0.0055 (13)	0.0108 (14)
C7	0.0362 (14)	0.0570 (18)	0.0422 (15)	−0.0004 (13)	0.0004 (12)	0.0008 (14)
C8	0.0380 (15)	0.0499 (18)	0.0459 (15)	−0.0004 (13)	0.0099 (12)	−0.0001 (13)
C9	0.0420 (15)	0.0419 (16)	0.0524 (16)	0.0021 (13)	0.0126 (13)	0.0004 (14)
C10	0.0477 (16)	0.0461 (17)	0.0504 (16)	0.0025 (14)	0.0135 (13)	−0.0036 (14)
C11	0.087 (2)	0.053 (2)	0.063 (2)	−0.0116 (18)	0.0278 (18)	−0.0115 (17)
C12	0.109 (3)	0.066 (2)	0.069 (2)	−0.005 (2)	0.039 (2)	−0.0194 (19)
C13	0.081 (2)	0.077 (3)	0.064 (2)	0.005 (2)	0.0358 (18)	−0.009 (2)
C14	0.0568 (19)	0.065 (2)	0.068 (2)	−0.0031 (16)	0.0286 (16)	−0.0037 (17)
C15	0.0459 (16)	0.0527 (18)	0.0514 (17)	0.0044 (14)	0.0143 (13)	−0.0034 (14)
C16	0.0464 (17)	0.060 (2)	0.0567 (18)	−0.0082 (15)	0.0155 (14)	−0.0056 (16)
C17	0.0455 (16)	0.0507 (18)	0.0445 (16)	−0.0046 (14)	0.0120 (13)	0.0022 (14)
C18	0.083 (2)	0.072 (2)	0.0506 (18)	0.0130 (19)	0.0235 (17)	0.0078 (17)
C19	0.108 (3)	0.097 (3)	0.062 (2)	0.017 (3)	0.041 (2)	−0.001 (2)
C20	0.082 (3)	0.073 (3)	0.089 (3)	0.014 (2)	0.042 (2)	−0.006 (2)
C21	0.062 (2)	0.058 (2)	0.073 (2)	0.0098 (17)	0.0187 (17)	0.0064 (17)
C22	0.0567 (18)	0.0525 (18)	0.0488 (17)	−0.0001 (15)	0.0180 (14)	0.0028 (14)

Geometric parameters (Å, º)

Si—O1	1.651 (2)	C7—C8	1.503 (4)
Si—C1	1.836 (4)	C7—C17	1.519 (4)
Si—C3	1.847 (3)	C7—H7	0.9800
Si—C2	1.854 (4)	C8—C9	1.348 (4)
O1—C5	1.396 (3)	C8—C16	1.449 (4)
O2—C9	1.351 (3)	C9—C10	1.452 (4)
O2—C5	1.466 (3)	C10—C11	1.386 (4)
O3—C15	1.377 (3)	C10—C15	1.389 (4)
O3—C16	1.380 (3)	C11—C12	1.370 (4)
O4—C16	1.206 (3)	C11—H11	0.9300
C1—H1A	0.9600	C12—C13	1.379 (5)
C1—H1B	0.9600	C12—H12	0.9300
C1—H1C	0.9600	C13—C14	1.368 (4)
C2—H2A	0.9600	C13—H13	0.9300
C2—H2B	0.9600	C14—C15	1.385 (4)
C2—H2C	0.9600	C14—H14	0.9300
C3—H3A	0.9600	C17—C18	1.376 (4)
C3—H3B	0.9600	C17—C22	1.386 (4)
C3—H3C	0.9600	C18—C19	1.379 (5)
C4—C5	1.521 (4)	C18—H18	0.9300
C4—H4A	0.9600	C19—C20	1.364 (5)
C4—H4B	0.9600	C19—H19	0.9300
C4—H4C	0.9600	C20—C21	1.372 (5)
C5—C6	1.506 (4)	C20—H20	0.9300
C6—C7	1.540 (4)	C21—C22	1.381 (4)
C6—H6A	0.9700	C21—H21	0.9300
C6—H6B	0.9700	C22—H22	0.9300
O1—Si—C1	103.17 (15)	C8—C7—H7	106.1
O1—Si—C3	110.76 (15)	C17—C7—H7	106.1
C1—Si—C3	110.9 (2)	C6—C7—H7	106.1
O1—Si—C2	112.81 (15)	C9—C8—C16	119.4 (3)
C1—Si—C2	109.85 (18)	C9—C8—C7	122.2 (3)
C3—Si—C2	109.2 (2)	C16—C8—C7	118.3 (2)
C5—O1—Si	135.16 (19)	C8—C9—O2	125.1 (2)
C9—O2—C5	117.4 (2)	C8—C9—C10	121.6 (3)
C15—O3—C16	121.4 (2)	O2—C9—C10	113.2 (2)
Si—C1—H1A	109.5	C11—C10—C15	118.1 (3)
Si—C1—H1B	109.5	C11—C10—C9	124.7 (3)
H1A—C1—H1B	109.5	C15—C10—C9	117.3 (3)
Si—C1—H1C	109.5	C12—C11—C10	120.9 (3)
H1A—C1—H1C	109.5	C12—C11—H11	119.5
H1B—C1—H1C	109.5	C10—C11—H11	119.5
Si—C2—H2A	109.5	C11—C12—C13	119.6 (3)
Si—C2—H2B	109.5	C11—C12—H12	120.2
H2A—C2—H2B	109.5	C13—C12—H12	120.2
Si—C2—H2C	109.5	C14—C13—C12	121.4 (3)
H2A—C2—H2C	109.5	C14—C13—H13	119.3
H2B—C2—H2C	109.5	C12—C13—H13	119.3
Si—C3—H3A	109.5	C13—C14—C15	118.3 (3)
Si—C3—H3B	109.5	C13—C14—H14	120.8
H3A—C3—H3B	109.5	C15—C14—H14	120.8
Si—C3—H3C	109.5	O3—C15—C14	117.0 (3)
H3A—C3—H3C	109.5	O3—C15—C10	121.4 (2)
H3B—C3—H3C	109.5	C14—C15—C10	121.7 (3)
C5—C4—H4A	109.5	O4—C16—O3	116.0 (3)
C5—C4—H4B	109.5	O4—C16—C8	125.3 (3)
H4A—C4—H4B	109.5	O3—C16—C8	118.7 (3)
C5—C4—H4C	109.5	C18—C17—C22	117.3 (3)
H4A—C4—H4C	109.5	C18—C17—C7	119.6 (3)
H4B—C4—H4C	109.5	C22—C17—C7	123.1 (2)
O1—C5—O2	108.4 (2)	C17—C18—C19	121.5 (3)
O1—C5—C6	109.2 (2)	C17—C18—H18	119.3
O2—C5—C6	109.9 (2)	C19—C18—H18	119.3
O1—C5—C4	111.8 (2)	C20—C19—C18	120.5 (3)
O2—C5—C4	104.0 (3)	C20—C19—H19	119.8
C6—C5—C4	113.4 (2)	C18—C19—H19	119.8
C5—C6—C7	112.9 (2)	C19—C20—C21	119.4 (3)
C5—C6—H6A	109.0	C19—C20—H20	120.3
C7—C6—H6A	109.0	C21—C20—H20	120.3
C5—C6—H6B	109.0	C20—C21—C22	120.0 (3)
C7—C6—H6B	109.0	C20—C21—H21	120.0
H6A—C6—H6B	107.8	C22—C21—H21	120.0
C8—C7—C17	115.3 (2)	C21—C22—C17	121.4 (3)
C8—C7—C6	107.9 (2)	C21—C22—H22	119.3
C17—C7—C6	114.5 (2)	C17—C22—H22	119.3
C1—Si—O1—C5	170.7 (3)	C10—C11—C12—C13	−0.1 (6)
C3—Si—O1—C5	−70.6 (3)	C11—C12—C13—C14	−1.0 (6)
C2—Si—O1—C5	52.2 (3)	C12—C13—C14—C15	1.2 (5)
Si—O1—C5—O2	47.6 (3)	C16—O3—C15—C14	−175.2 (3)
Si—O1—C5—C6	167.33 (19)	C16—O3—C15—C10	4.5 (4)
Si—O1—C5—C4	−66.4 (3)	C13—C14—C15—O3	179.3 (3)
C9—O2—C5—O1	82.2 (3)	C13—C14—C15—C10	−0.3 (5)
C9—O2—C5—C6	−37.0 (3)	C11—C10—C15—O3	179.6 (3)
C9—O2—C5—C4	−158.7 (2)	C9—C10—C15—O3	−1.4 (4)
O1—C5—C6—C7	−61.1 (3)	C11—C10—C15—C14	−0.8 (4)
O2—C5—C6—C7	57.6 (3)	C9—C10—C15—C14	178.2 (3)
C4—C5—C6—C7	173.5 (3)	C15—O3—C16—O4	177.0 (3)
C5—C6—C7—C8	−45.9 (3)	C15—O3—C16—C8	−3.8 (4)
C5—C6—C7—C17	84.0 (3)	C9—C8—C16—O4	179.2 (3)
C17—C7—C8—C9	−113.8 (3)	C7—C8—C16—O4	−4.2 (5)
C6—C7—C8—C9	15.6 (4)	C9—C8—C16—O3	0.1 (4)
C17—C7—C8—C16	69.7 (3)	C7—C8—C16—O3	176.7 (2)
C6—C7—C8—C16	−160.9 (2)	C8—C7—C17—C18	−166.7 (3)
C16—C8—C9—O2	−179.2 (3)	C6—C7—C17—C18	67.1 (4)
C7—C8—C9—O2	4.3 (4)	C8—C7—C17—C22	11.7 (4)
C16—C8—C9—C10	3.0 (4)	C6—C7—C17—C22	−114.5 (3)
C7—C8—C9—C10	−173.5 (2)	C22—C17—C18—C19	0.9 (5)
C5—O2—C9—C8	6.8 (4)	C7—C17—C18—C19	179.3 (3)
C5—O2—C9—C10	−175.2 (2)	C17—C18—C19—C20	−0.5 (6)
C8—C9—C10—C11	176.5 (3)	C18—C19—C20—C21	−0.1 (6)
O2—C9—C10—C11	−1.5 (4)	C19—C20—C21—C22	0.2 (6)
C8—C9—C10—C15	−2.4 (4)	C20—C21—C22—C17	0.2 (5)
O2—C9—C10—C15	179.6 (2)	C18—C17—C22—C21	−0.7 (4)
C15—C10—C11—C12	1.0 (5)	C7—C17—C22—C21	−179.1 (3)
C9—C10—C11—C12	−178.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O3^i	0.96	2.58	3.482 (4)	156
C14—H14···O4^ii	0.93	2.55	3.463 (4)	168
C6—H6A···Cg(B)^iii	0.97	2.81	3.773 (3)	175
C21—H21···Cg(A)^iv	0.93	2.96	3.815 (4)	153

Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y+1, −z; (iii) −x+3/2, y−1/2, −z+1/2; (iv) −x+1, −y+1, −z.