3-Benzoyl-2-hydroxy-2-methyl­chromene

In the title compound, C₁₇H₁₄O₃, the conformation of the pyran ring is intermediate between sofa and half-chair. In the crystal structure, the hydroxyl and carbonyl O atoms are involved in O—H...O intermolecular hydrogen bonding, forming chains along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.050
• wR factor = 0.171
• Data-to-parameter ratio = 9.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           74.88
         From the CIF: _reflns_number_total               1645
         Count of symmetry unique reflns         1649
         Completeness (_total/calc)             99.76%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.

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Computing details

Data collection: CAD-4 EXPRESS (Enraf Nonius, 1994); 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 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

2-Hydroxy-2-methyl-3-benzoylchromene

Crystal data

C17H14O3	F(000) = 560
Mr = 266.28	Dx = 1.323 Mg m^−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 5.691 (4) Å	θ = 15–35°
b = 6.902 (3) Å	µ = 0.73 mm^−1
c = 34.044 (2) Å	T = 293 K
V = 1337.2 (11) Å^3	Prism, pale yellow
Z = 4	0.20 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD4 diffractometer	Rint = 0.00
Radiation source: Enraf Nonius FR590	θmax = 74.9°, θmin = 2.6°
Graphite monochromator	h = 0→7
non–profiled ω/2θ scans	k = 0→8
1645 measured reflections	l = 0→42
1645 independent reflections	2 standard reflections every 60 reflections
1563 reflections with I > 2σ(I)	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)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.171	w = 1/[σ^2(Fo^2) + (0.0983P)^2 + 0.8035P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1645 reflections	Δρmax = 0.34 e Å^−3
183 parameters	Δρmin = −0.22 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: 0.0103 (16)

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
O1	0.0360 (5)	−0.2317 (3)	0.06510 (7)	0.0521 (7)
C2	0.1377 (6)	−0.2490 (5)	0.10378 (9)	0.0394 (7)
C3	0.1996 (6)	−0.0488 (4)	0.12031 (9)	0.0369 (7)
C4	0.0678 (6)	0.1039 (4)	0.10900 (9)	0.0371 (7)
H4	0.0896	0.2226	0.1214	0.044*
C5	−0.2556 (7)	0.2408 (5)	0.06775 (9)	0.0455 (8)
H5	−0.2500	0.3573	0.0815	0.055*
C6	−0.4121 (8)	0.2184 (6)	0.03701 (11)	0.0525 (9)
H6	−0.5134	0.3191	0.0304	0.063*
C7	−0.4185 (7)	0.0460 (6)	0.01603 (10)	0.0508 (9)
H7	−0.5245	0.0313	−0.0045	0.061*
C8	−0.2677 (8)	−0.1039 (5)	0.02561 (10)	0.0521 (9)
H8	−0.2692	−0.2180	0.0111	0.063*
C9	−0.1146 (6)	−0.0837 (5)	0.05693 (9)	0.0403 (7)
C10	−0.1055 (6)	0.0888 (4)	0.07828 (8)	0.0363 (7)
O11	−0.0249 (5)	−0.3412 (3)	0.12859 (8)	0.0535 (7)
H11	−0.1231	−0.2623	0.1360	0.080*
C12	0.3389 (7)	−0.3872 (5)	0.09769 (12)	0.0504 (9)
H12A	0.3960	−0.4306	0.1227	0.076*
H12B	0.4630	−0.3226	0.0838	0.076*
H12C	0.2861	−0.4966	0.0827	0.076*
C13	0.3934 (6)	−0.0174 (5)	0.14832 (9)	0.0413 (7)
O14	0.5707 (5)	−0.1154 (4)	0.14903 (9)	0.0621 (8)
C15	0.3751 (6)	0.1497 (5)	0.17612 (9)	0.0438 (8)
C16	0.5582 (7)	0.2787 (6)	0.17914 (11)	0.0533 (9)
H16	0.6905	0.2627	0.1634	0.064*
C17	0.5483 (10)	0.4318 (7)	0.20523 (14)	0.0728 (13)
H17	0.6703	0.5213	0.2064	0.087*
C18	0.3570 (10)	0.4508 (8)	0.22942 (14)	0.0794 (15)
H18	0.3514	0.5513	0.2476	0.095*
C19	0.1716 (9)	0.3206 (8)	0.22692 (13)	0.0741 (14)
H19	0.0428	0.3338	0.2435	0.089*
C20	0.1781 (7)	0.1728 (7)	0.20007 (10)	0.0550 (10)
H20	0.0516	0.0882	0.1978	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0678 (17)	0.0366 (12)	0.0520 (12)	0.0130 (13)	−0.0085 (12)	−0.0097 (10)
C2	0.0376 (16)	0.0313 (14)	0.0492 (16)	0.0067 (15)	0.0044 (14)	0.0025 (13)
C3	0.0345 (15)	0.0349 (15)	0.0413 (14)	0.0028 (14)	0.0047 (12)	0.0011 (12)
C4	0.0383 (15)	0.0321 (14)	0.0409 (14)	0.0002 (14)	0.0020 (13)	−0.0010 (12)
C5	0.0525 (19)	0.0344 (15)	0.0497 (16)	0.0096 (17)	−0.0014 (15)	0.0002 (13)
C6	0.055 (2)	0.0493 (19)	0.0531 (18)	0.014 (2)	−0.0049 (17)	0.0052 (15)
C7	0.0451 (18)	0.057 (2)	0.0509 (17)	−0.0021 (19)	−0.0077 (16)	0.0023 (16)
C8	0.065 (2)	0.0437 (18)	0.0481 (17)	−0.002 (2)	−0.0020 (17)	−0.0063 (14)
C9	0.0436 (18)	0.0332 (15)	0.0441 (15)	0.0041 (15)	0.0047 (14)	0.0010 (12)
C10	0.0345 (15)	0.0333 (14)	0.0411 (14)	0.0021 (14)	0.0038 (12)	0.0020 (12)
O11	0.0491 (14)	0.0377 (12)	0.0736 (16)	0.0022 (12)	0.0169 (13)	0.0055 (12)
C12	0.0446 (19)	0.0352 (16)	0.071 (2)	0.0110 (17)	0.0070 (18)	−0.0034 (15)
C13	0.0351 (15)	0.0424 (16)	0.0464 (16)	0.0055 (15)	0.0041 (13)	0.0044 (13)
O14	0.0392 (13)	0.0670 (17)	0.0800 (17)	0.0194 (15)	−0.0069 (13)	−0.0070 (15)
C15	0.0431 (17)	0.0477 (17)	0.0406 (14)	0.0068 (17)	−0.0067 (14)	0.0026 (14)
C16	0.0405 (17)	0.065 (2)	0.0542 (19)	−0.001 (2)	−0.0074 (16)	0.0022 (18)
C17	0.075 (3)	0.069 (3)	0.075 (3)	−0.007 (3)	−0.028 (3)	−0.009 (2)
C18	0.084 (3)	0.082 (3)	0.072 (3)	0.022 (3)	−0.021 (3)	−0.032 (3)
C19	0.056 (2)	0.103 (4)	0.063 (2)	0.014 (3)	−0.005 (2)	−0.028 (3)
C20	0.0425 (18)	0.072 (2)	0.0500 (17)	0.004 (2)	0.0027 (16)	−0.0058 (19)

Geometric parameters (Å, º)

O1—C9	1.363 (4)	C9—C10	1.396 (4)
O1—C2	1.443 (4)	O11—H11	0.82
C2—O11	1.405 (4)	C12—H12A	0.96
C2—C12	1.505 (5)	C12—H12B	0.96
C2—C3	1.533 (4)	C12—H12C	0.96
C3—C4	1.350 (4)	C13—O14	1.215 (4)
C3—C13	1.474 (5)	C13—C15	1.496 (5)
C4—C10	1.442 (4)	C15—C16	1.375 (5)
C4—H4	0.93	C15—C20	1.395 (5)
C5—C6	1.383 (5)	C16—C17	1.382 (6)
C5—C10	1.400 (4)	C16—H16	0.93
C5—H5	0.93	C17—C18	1.371 (8)
C6—C7	1.389 (5)	C17—H17	0.93
C6—H6	0.93	C18—C19	1.388 (8)
C7—C8	1.383 (5)	C18—H18	0.93
C7—H7	0.93	C19—C20	1.370 (6)
C8—C9	1.384 (5)	C19—H19	0.93
C8—H8	0.93	C20—H20	0.93
C9—O1—C2	120.0 (2)	C5—C10—C4	123.3 (3)
O11—C2—O1	108.8 (3)	C2—O11—H11	109.5
O11—C2—C12	107.3 (3)	C2—C12—H12A	109.5
O1—C2—C12	103.4 (3)	C2—C12—H12B	109.5
O11—C2—C3	109.8 (3)	H12A—C12—H12B	109.5
O1—C2—C3	110.7 (2)	C2—C12—H12C	109.5
C12—C2—C3	116.5 (3)	H12A—C12—H12C	109.5
C4—C3—C13	119.1 (3)	H12B—C12—H12C	109.5
C4—C3—C2	118.1 (3)	O14—C13—C3	123.5 (3)
C13—C3—C2	122.8 (3)	O14—C13—C15	118.3 (3)
C3—C4—C10	122.0 (3)	C3—C13—C15	118.1 (3)
C3—C4—H4	119.0	C16—C15—C20	119.5 (3)
C10—C4—H4	119.0	C16—C15—C13	119.6 (3)
C6—C5—C10	120.2 (3)	C20—C15—C13	120.9 (3)
C6—C5—H5	119.9	C15—C16—C17	120.8 (4)
C10—C5—H5	119.9	C15—C16—H16	119.6
C5—C6—C7	120.1 (3)	C17—C16—H16	119.6
C5—C6—H6	119.9	C18—C17—C16	119.4 (5)
C7—C6—H6	119.9	C18—C17—H17	120.3
C8—C7—C6	120.2 (3)	C16—C17—H17	120.3
C8—C7—H7	119.9	C17—C18—C19	120.3 (4)
C6—C7—H7	119.9	C17—C18—H18	119.8
C9—C8—C7	119.8 (3)	C19—C18—H18	119.8
C9—C8—H8	120.1	C20—C19—C18	120.1 (4)
C7—C8—H8	120.1	C20—C19—H19	119.9
O1—C9—C8	118.5 (3)	C18—C19—H19	119.9
O1—C9—C10	120.6 (3)	C19—C20—C15	119.8 (4)
C8—C9—C10	120.7 (3)	C19—C20—H20	120.1
C9—C10—C5	118.9 (3)	C15—C20—H20	120.1
C9—C10—C4	117.7 (3)
C9—O1—C2—O11	82.1 (4)	C8—C9—C10—C4	−176.3 (3)
C9—O1—C2—C12	−164.2 (3)	C6—C5—C10—C9	0.9 (5)
C9—O1—C2—C3	−38.6 (4)	C6—C5—C10—C4	177.7 (3)
O11—C2—C3—C4	−90.0 (3)	C3—C4—C10—C9	−7.7 (5)
O1—C2—C3—C4	30.1 (4)	C3—C4—C10—C5	175.5 (3)
C12—C2—C3—C4	147.9 (3)	C4—C3—C13—O14	−150.4 (3)
O11—C2—C3—C13	89.0 (4)	C2—C3—C13—O14	30.6 (5)
O1—C2—C3—C13	−150.9 (3)	C4—C3—C13—C15	26.7 (4)
C12—C2—C3—C13	−33.1 (4)	C2—C3—C13—C15	−152.3 (3)
C13—C3—C4—C10	172.4 (3)	O14—C13—C15—C16	48.7 (5)
C2—C3—C4—C10	−8.6 (5)	C3—C13—C15—C16	−128.6 (3)
C10—C5—C6—C7	−1.1 (6)	O14—C13—C15—C20	−129.0 (4)
C5—C6—C7—C8	−0.3 (6)	C3—C13—C15—C20	53.7 (4)
C6—C7—C8—C9	1.8 (6)	C20—C15—C16—C17	−0.7 (5)
C2—O1—C9—C8	−158.5 (3)	C13—C15—C16—C17	−178.5 (3)
C2—O1—C9—C10	25.0 (5)	C15—C16—C17—C18	2.5 (6)
C7—C8—C9—O1	−178.4 (3)	C16—C17—C18—C19	−1.9 (7)
C7—C8—C9—C10	−1.9 (5)	C17—C18—C19—C20	−0.4 (8)
O1—C9—C10—C5	177.0 (3)	C18—C19—C20—C15	2.1 (7)
C8—C9—C10—C5	0.6 (5)	C16—C15—C20—C19	−1.6 (6)
O1—C9—C10—C4	0.0 (5)	C13—C15—C20—C19	176.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O14	0.96	2.55	2.884 (5)	100
O11—H11···O14^i	0.82	2.06	2.865 (4)	165

Symmetry code: (i) x−1, y, z.