1-(1-Benzo­furan-2-yl)-2-mesityl­ethano­ne

The benzo­furan ring system in the title compound, C₁₉H₁₈O₂, is planar and is linked to the mesityl group via an acetyl group. In the crystal structure, symmetry-related mol­ecules are connected to form chains by C—H...O intermolecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.058
• wR factor = 0.154
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.87
PLAT351_ALERT_3_A Long    C-H Bond (0.96A)   C19    -   H5_a   ...       1.41 Ang.
PLAT411_ALERT_2_A Short Inter H...H Contact  H4     ..  H15     ..       1.86 Ang.
PLAT411_ALERT_2_A Short Inter H...H Contact  H5     ..  H19C    ..       1.86 Ang.
PLAT413_ALERT_2_A Short Inter XH3 .. XHn     H18B   ..  H19C    ..       1.85 Ang.

Alert level B
REFLT03_ALERT_3_B  Reflection count < 90% complete (theta max?)
           From the CIF: _diffrn_reflns_theta_max           25.65
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               2467
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         2834
           Completeness (_total/calc)             87.05%
PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low ....       0.87
PLAT411_ALERT_2_B Short Inter H...H Contact  H5     ..  H15     ..       1.94 Ang.

Alert level C
PLAT147_ALERT_1_C su on Symmetry Constrained Cell Angle(s) .......          ?
PLAT320_ALERT_2_C Check Hybridisation of  C19    in Main Residue .          ?
PLAT322_ALERT_2_C Check Hybridisation of  H19A   in Main Residue .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ......        C18

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 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 EXPRESS (Enraf-Nonius, 1993); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97; molecular graphics: PLATON (Spek, 2000); software used to prepare material for publication: SHELXL97.

(2)

Crystal data

C19H18O2	F(000) = 592
Mr = 278.33	Dx = 1.232 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.133 (5) Å	θ = 2.6–25.7°
b = 15.762 (5) Å	µ = 0.08 mm^−1
c = 11.752 (5) Å	T = 293 K
β = 95.231 (5)°	Prism, colourless
V = 1500.2 (12) Å^3	0.25 × 0.20 × 0.15 mm
Z = 4

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.034
ω/2θ scans	θmax = 25.7°
Absorption correction: ψ scan (MolEN; Fair, 1990)	h = −9→9
Tmin = 0.973, Tmax = 0.980	k = −19→0
2570 measured reflections	l = −14→0
2467 independent reflections	3 standard reflections every 120 min
1330 reflections with I > 2σ(I)	intensity decay: 0.7%

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)] = 0.058	H-atom parameters constrained
wR(F^2) = 0.154	w = 1/[σ^2(Fo^2) + (0.0891P)^2 + 0.3519P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.0001
2467 reflections	Δρmax = 0.24 e Å^−3
191 parameters	Δρmin = −0.21 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: 0.012 (3)

Special details

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
C1	0.2563 (4)	−0.0657 (2)	0.9840 (3)	0.0525 (9)
C2	0.1770 (5)	−0.0889 (3)	1.0784 (3)	0.0717 (12)
H2	0.0810	−0.0623	1.0970	0.086*
C3	0.2491 (5)	−0.1535 (3)	1.1424 (3)	0.0751 (13)
H3	0.2012	−0.1712	1.2073	0.090*
C4	0.3915 (6)	−0.1935 (3)	1.1137 (3)	0.0759 (13)
H4	0.4359	−0.2377	1.1590	0.091*
C5	0.4684 (5)	−0.1688 (3)	1.0193 (3)	0.0677 (11)
H5	0.5648	−0.1953	1.0012	0.081*
C6	0.3983 (4)	−0.1033 (2)	0.9518 (3)	0.0524 (9)
C7	0.4327 (4)	−0.0615 (2)	0.8486 (3)	0.0561 (10)
H7	0.5215	−0.0724	0.8063	0.067*
C8	0.3135 (4)	−0.0036 (2)	0.8239 (3)	0.0489 (9)
C9	0.2804 (4)	0.0570 (2)	0.7308 (3)	0.0512 (9)
C10	0.4041 (4)	0.0576 (2)	0.6416 (3)	0.0553 (10)
H10A	0.4978	0.0922	0.6696	0.066*
H10B	0.4439	0.0002	0.6325	0.066*
C11	0.3377 (4)	0.0905 (2)	0.5262 (3)	0.0451 (9)
C12	0.2390 (4)	0.0379 (2)	0.4535 (3)	0.0517 (9)
C13	0.1784 (5)	0.0680 (3)	0.3463 (3)	0.0633 (11)
H13	0.1119	0.0327	0.2983	0.076*
C14	0.2132 (5)	0.1476 (3)	0.3094 (3)	0.0659 (11)
C15	0.3131 (5)	0.1992 (3)	0.3822 (3)	0.0619 (11)
H15	0.3396	0.2533	0.3583	0.074*
C16	0.3742 (4)	0.1715 (2)	0.4900 (3)	0.0505 (9)
C17	0.1954 (5)	−0.0509 (2)	0.4877 (4)	0.0731 (12)
H17A	0.2454	−0.0625	0.5633	0.110*
H17B	0.2353	−0.0908	0.4350	0.110*
H17C	0.0776	−0.0560	0.4868	0.110*
C18	0.1447 (6)	0.1799 (4)	0.1937 (4)	0.1065 (18)
H18A	0.0786	0.1365	0.1548	0.160*
H18B	0.2342	0.1946	0.1495	0.160*
H18C	0.0779	0.2292	0.2033	0.160*
C19	0.4783 (5)	0.2325 (3)	0.5653 (4)	0.0738 (12)
H19A	0.4915	0.2845	0.5246	0.111*
H19B	0.5848	0.2077	0.5858	0.111*
H19C	0.4249	0.2439	0.6332	0.111*
O1	0.2027 (3)	−0.00337 (17)	0.9070 (2)	0.0617 (8)
O2	0.1611 (3)	0.10315 (18)	0.7255 (2)	0.0755 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.052 (2)	0.065 (2)	0.040 (2)	0.0026 (19)	0.0055 (17)	0.0048 (18)
C2	0.058 (2)	0.108 (3)	0.051 (2)	0.005 (2)	0.013 (2)	0.010 (2)
C3	0.075 (3)	0.101 (4)	0.050 (2)	−0.016 (3)	0.009 (2)	0.009 (2)
C4	0.100 (4)	0.074 (3)	0.052 (2)	0.002 (3)	0.002 (2)	0.011 (2)
C5	0.076 (3)	0.072 (3)	0.055 (2)	0.017 (2)	0.006 (2)	0.001 (2)
C6	0.059 (2)	0.057 (2)	0.041 (2)	0.0049 (19)	0.0045 (17)	−0.0019 (19)
C7	0.055 (2)	0.064 (2)	0.051 (2)	0.011 (2)	0.0150 (18)	0.0002 (19)
C8	0.0431 (19)	0.060 (2)	0.045 (2)	0.0055 (18)	0.0131 (16)	−0.0024 (18)
C9	0.048 (2)	0.062 (2)	0.044 (2)	0.0093 (19)	0.0099 (17)	−0.0008 (19)
C10	0.049 (2)	0.066 (2)	0.053 (2)	0.0080 (18)	0.0158 (17)	0.0051 (19)
C11	0.0399 (18)	0.052 (2)	0.045 (2)	0.0040 (16)	0.0149 (16)	0.0007 (17)
C12	0.0434 (19)	0.057 (2)	0.057 (2)	0.0009 (18)	0.0176 (18)	−0.003 (2)
C13	0.050 (2)	0.083 (3)	0.057 (3)	0.005 (2)	0.0085 (19)	−0.012 (2)
C14	0.062 (3)	0.087 (3)	0.050 (2)	0.016 (2)	0.016 (2)	0.006 (2)
C15	0.066 (2)	0.057 (2)	0.066 (3)	0.008 (2)	0.029 (2)	0.012 (2)
C16	0.051 (2)	0.050 (2)	0.053 (2)	0.0052 (17)	0.0181 (18)	0.0005 (18)
C17	0.063 (3)	0.062 (3)	0.097 (3)	−0.004 (2)	0.024 (2)	−0.006 (2)
C18	0.109 (4)	0.155 (5)	0.055 (3)	0.033 (4)	0.008 (3)	0.024 (3)
C19	0.077 (3)	0.062 (3)	0.085 (3)	−0.005 (2)	0.020 (2)	−0.011 (2)
O1	0.0527 (15)	0.0825 (19)	0.0529 (15)	0.0164 (13)	0.0201 (13)	0.0080 (14)
O2	0.0720 (18)	0.096 (2)	0.0620 (17)	0.0372 (17)	0.0236 (14)	0.0164 (15)

Geometric parameters (Å, º)

C1—O1	1.379 (4)	C11—C16	1.386 (5)
C1—C2	1.382 (5)	C11—C12	1.391 (5)
C1—C6	1.381 (5)	C12—C13	1.393 (5)
C2—C3	1.367 (6)	C12—C17	1.508 (5)
C2—H2	0.9300	C13—C14	1.366 (5)
C3—C4	1.387 (6)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.387 (6)
C4—C5	1.378 (6)	C14—C18	1.510 (5)
C4—H4	0.9300	C15—C16	1.388 (5)
C5—C6	1.392 (5)	C15—H15	0.9300
C5—H5	0.9300	C16—C19	1.512 (5)
C6—C7	1.430 (5)	C17—H17A	0.9600
C7—C8	1.343 (5)	C17—H17B	0.9600
C7—H7	0.9300	C17—H17C	0.9600
C8—O1	1.389 (4)	C18—H18A	0.9600
C8—C9	1.458 (5)	C18—H18B	0.9600
C9—O2	1.210 (4)	C18—H18C	0.9600
C9—C10	1.517 (5)	C19—H19A	0.9600
C10—C11	1.506 (5)	C19—H19B	0.9600
C10—H10A	0.9700	C19—H19C	0.9600
C10—H10B	0.9700
O1—C1—C2	124.9 (3)	C12—C11—C10	119.2 (3)
O1—C1—C6	110.4 (3)	C11—C12—C13	119.3 (4)
C2—C1—C6	124.7 (4)	C11—C12—C17	121.7 (3)
C3—C2—C1	115.5 (4)	C13—C12—C17	119.0 (4)
C3—C2—H2	122.2	C14—C13—C12	122.2 (4)
C1—C2—H2	122.2	C14—C13—H13	118.9
C2—C3—C4	122.0 (4)	C12—C13—H13	118.9
C2—C3—H3	119.0	C13—C14—C15	118.0 (4)
C4—C3—H3	119.0	C13—C14—C18	121.7 (4)
C5—C4—C3	121.2 (4)	C15—C14—C18	120.3 (4)
C5—C4—H4	119.4	C16—C15—C14	121.3 (4)
C3—C4—H4	119.4	C16—C15—H15	119.3
C4—C5—C6	118.4 (4)	C14—C15—H15	119.3
C4—C5—H5	120.8	C15—C16—C11	120.0 (4)
C6—C5—H5	120.8	C15—C16—C19	118.0 (4)
C1—C6—C5	118.1 (3)	C11—C16—C19	122.0 (3)
C1—C6—C7	105.5 (3)	C12—C17—H17A	109.5
C5—C6—C7	136.3 (3)	C12—C17—H17B	109.5
C8—C7—C6	107.7 (3)	H17A—C17—H17B	109.5
C8—C7—H7	126.2	C12—C17—H17C	109.5
C6—C7—H7	126.2	H17A—C17—H17C	109.5
C7—C8—O1	110.5 (3)	H17B—C17—H17C	109.5
C7—C8—C9	133.4 (3)	C14—C18—H18A	109.5
O1—C8—C9	116.0 (3)	C14—C18—H18B	109.5
O2—C9—C8	121.6 (3)	H18A—C18—H18B	109.5
O2—C9—C10	122.7 (3)	C14—C18—H18C	109.5
C8—C9—C10	115.7 (3)	H18A—C18—H18C	109.5
C11—C10—C9	114.8 (3)	H18B—C18—H18C	109.5
C11—C10—H10A	108.6	C16—C19—H19A	109.5
C9—C10—H10A	108.6	C16—C19—H19B	109.5
C11—C10—H10B	108.6	H19A—C19—H19B	109.5
C9—C10—H10B	108.6	C16—C19—H19C	109.5
H10A—C10—H10B	107.6	H19A—C19—H19C	109.5
C16—C11—C12	119.2 (3)	H19B—C19—H19C	109.5
C16—C11—C10	121.6 (3)	C1—O1—C8	105.9 (3)
O1—C1—C2—C3	178.7 (3)	C9—C10—C11—C12	−78.0 (4)
O1—C1—C6—C5	−179.1 (3)	C10—C11—C12—C13	−179.5 (3)
C2—C1—C6—C7	178.2 (4)	C16—C11—C12—C17	179.8 (3)
C4—C5—C6—C7	−177.5 (4)	C17—C12—C13—C14	−179.8 (3)
C5—C6—C7—C8	177.8 (4)	C12—C13—C14—C18	−179.1 (4)
C6—C7—C8—C9	−179.3 (4)	C18—C14—C15—C16	178.5 (3)
C7—C8—C9—O2	178.9 (4)	C14—C15—C16—C19	−178.4 (3)
O1—C8—C9—C10	178.8 (3)	C10—C11—C16—C15	178.9 (3)
O2—C9—C10—C11	−23.8 (5)	C12—C11—C16—C19	179.0 (3)
C8—C9—C10—C11	155.8 (3)	C2—C1—O1—C8	−177.4 (4)
C9—C10—C11—C16	102.8 (4)	C9—C8—O1—C1	179.0 (3)