3-(4-Methyl­phen­yl)-4H-chromen-4-one

In the title compound, C₁₆H₁₂O₂, the dihedral angle formed between the plane of the chromenone ring system (r.m.s. deviation = 0.031 Å) and the pendant benzene ring is 31.09 (5)°. In the crystal, weak C—H...O hydrogen bonds link the mol­ecules into C(6) chains propagating along the a-axis direction.

Key indicators

• Single-crystal X-ray study
• T = 223 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.044
• wR factor = 0.124
• Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.365 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         18 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          5 Note

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          6 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          4 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         20 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   1 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
   4 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

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Computing details

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

3-(4-Methylphenyl)-4H-chromen-4-one

Crystal data

C16H12O2	Z = 2
Mr = 236.26	F(000) = 248
Triclinic, P1	Dx = 1.339 Mg m^−3
a = 6.4514 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.0785 (4) Å	Cell parameters from 7663 reflections
c = 13.3144 (7) Å	θ = 3.0–28.3°
α = 78.906 (2)°	µ = 0.09 mm^−1
β = 85.276 (2)°	T = 223 K
γ = 79.628 (2)°	Block, colourless
V = 586.19 (5) Å^3	0.56 × 0.31 × 0.12 mm

Data collection

Bruker PHOTON II M14 CCD diffractometer	2459 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.032
Absorption correction: multi-scan (SADABS; Bruker, 2012)	θmax = 28.3°, θmin = 3.0°
Tmin = 0.666, Tmax = 0.746	h = −8→8
18172 measured reflections	k = −9→9
2904 independent reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.124	w = 1/[σ^2(Fo^2) + (0.0506P)^2 + 0.2032P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2904 reflections	Δρmax = 0.27 e Å^−3
164 parameters	Δρmin = −0.22 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.56922 (19)	0.72771 (17)	0.62667 (10)	0.0304 (3)
O1	0.72856 (15)	0.67806 (17)	0.67655 (8)	0.0452 (3)
C2	0.35627 (19)	0.78209 (17)	0.67070 (9)	0.0290 (3)
C3	0.19573 (19)	0.84130 (19)	0.60689 (9)	0.0318 (3)
H3	0.0619	0.8826	0.6365	0.038*
O2	0.20859 (13)	0.84701 (14)	0.50433 (7)	0.0338 (2)
C4	0.40159 (19)	0.78707 (17)	0.45916 (9)	0.0294 (3)
C5	0.4074 (2)	0.7839 (2)	0.35475 (10)	0.0365 (3)
H5	0.2836	0.8215	0.3182	0.044*
C6	0.5979 (2)	0.7246 (2)	0.30617 (11)	0.0408 (3)
H6	0.6040	0.7197	0.2359	0.049*
C7	0.7824 (2)	0.6717 (2)	0.36019 (11)	0.0416 (3)
H7	0.9121	0.6326	0.3263	0.050*
C8	0.7736 (2)	0.67708 (19)	0.46305 (11)	0.0361 (3)
H8	0.8984	0.6430	0.4989	0.043*
C9	0.58123 (19)	0.73260 (16)	0.51535 (9)	0.0289 (3)
C10	0.3097 (2)	0.77022 (18)	0.78255 (9)	0.0319 (3)
C11	0.4540 (2)	0.8019 (2)	0.84770 (11)	0.0408 (3)
H11	0.5867	0.8302	0.8209	0.049*
C12	0.4033 (3)	0.7920 (2)	0.95158 (11)	0.0467 (4)
H12	0.5035	0.8125	0.9940	0.056*
C13	0.2093 (3)	0.7528 (2)	0.99470 (11)	0.0450 (3)
C14	0.0661 (2)	0.7211 (2)	0.93000 (11)	0.0469 (4)
H14	−0.0672	0.6952	0.9570	0.056*
C15	0.1159 (2)	0.7269 (2)	0.82625 (10)	0.0400 (3)
H15	0.0173	0.7012	0.7846	0.048*
C16	0.1555 (3)	0.7426 (3)	1.10810 (12)	0.0646 (5)
H16A	0.2235	0.6185	1.1454	0.097*
H16B	0.0038	0.7546	1.1206	0.097*
H16C	0.2046	0.8482	1.1310	0.097*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0281 (6)	0.0288 (6)	0.0353 (6)	−0.0060 (4)	−0.0082 (5)	−0.0047 (5)
O1	0.0290 (5)	0.0644 (7)	0.0421 (5)	−0.0023 (4)	−0.0131 (4)	−0.0094 (5)
C2	0.0293 (6)	0.0282 (6)	0.0307 (6)	−0.0069 (4)	−0.0057 (4)	−0.0047 (4)
C3	0.0274 (6)	0.0379 (6)	0.0298 (6)	−0.0038 (5)	−0.0036 (4)	−0.0062 (5)
O2	0.0263 (4)	0.0444 (5)	0.0301 (4)	−0.0018 (4)	−0.0074 (3)	−0.0066 (4)
C4	0.0288 (6)	0.0273 (6)	0.0328 (6)	−0.0054 (4)	−0.0038 (5)	−0.0058 (4)
C5	0.0398 (7)	0.0375 (7)	0.0338 (6)	−0.0075 (5)	−0.0081 (5)	−0.0068 (5)
C6	0.0504 (8)	0.0404 (7)	0.0335 (6)	−0.0100 (6)	0.0016 (6)	−0.0106 (5)
C7	0.0389 (7)	0.0401 (7)	0.0460 (8)	−0.0056 (6)	0.0061 (6)	−0.0133 (6)
C8	0.0296 (6)	0.0344 (6)	0.0446 (7)	−0.0040 (5)	−0.0030 (5)	−0.0085 (5)
C9	0.0290 (6)	0.0249 (5)	0.0337 (6)	−0.0060 (4)	−0.0046 (5)	−0.0048 (4)
C10	0.0344 (6)	0.0315 (6)	0.0304 (6)	−0.0056 (5)	−0.0066 (5)	−0.0047 (5)
C11	0.0408 (7)	0.0481 (8)	0.0369 (7)	−0.0140 (6)	−0.0080 (6)	−0.0078 (6)
C12	0.0553 (9)	0.0543 (9)	0.0347 (7)	−0.0139 (7)	−0.0145 (6)	−0.0088 (6)
C13	0.0572 (9)	0.0460 (8)	0.0302 (7)	−0.0050 (7)	−0.0050 (6)	−0.0054 (6)
C14	0.0421 (8)	0.0615 (10)	0.0356 (7)	−0.0105 (7)	0.0009 (6)	−0.0048 (6)
C15	0.0356 (7)	0.0516 (8)	0.0341 (7)	−0.0112 (6)	−0.0052 (5)	−0.0058 (6)
C16	0.0831 (13)	0.0786 (13)	0.0306 (8)	−0.0110 (10)	−0.0025 (8)	−0.0086 (8)

Geometric parameters (Å, º)

C1—O1	1.2304 (15)	C8—C9	1.4026 (18)
C1—C2	1.4638 (17)	C8—H8	0.9400
C1—C9	1.4719 (17)	C10—C15	1.3947 (18)
C2—C3	1.3497 (16)	C10—C11	1.3974 (18)
C2—C10	1.4840 (17)	C11—C12	1.386 (2)
C3—O2	1.3544 (15)	C11—H11	0.9400
C3—H3	0.9400	C12—C13	1.385 (2)
O2—C4	1.3699 (15)	C12—H12	0.9400
C4—C9	1.3865 (16)	C13—C14	1.388 (2)
C4—C5	1.3919 (17)	C13—C16	1.512 (2)
C5—C6	1.376 (2)	C14—C15	1.3866 (19)
C5—H5	0.9400	C14—H14	0.9400
C6—C7	1.397 (2)	C15—H15	0.9400
C6—H6	0.9400	C16—H16A	0.9700
C7—C8	1.374 (2)	C16—H16B	0.9700
C7—H7	0.9400	C16—H16C	0.9700
O1—C1—C2	124.34 (12)	C4—C9—C1	121.04 (11)
O1—C1—C9	120.97 (12)	C8—C9—C1	121.16 (11)
C2—C1—C9	114.68 (10)	C15—C10—C11	117.53 (12)
C3—C2—C1	118.45 (11)	C15—C10—C2	120.11 (11)
C3—C2—C10	118.92 (11)	C11—C10—C2	122.36 (12)
C1—C2—C10	122.62 (10)	C12—C11—C10	120.57 (13)
C2—C3—O2	126.36 (11)	C12—C11—H11	119.7
C2—C3—H3	116.8	C10—C11—H11	119.7
O2—C3—H3	116.8	C13—C12—C11	121.94 (13)
C3—O2—C4	118.06 (9)	C13—C12—H12	119.0
O2—C4—C9	121.22 (11)	C11—C12—H12	119.0
O2—C4—C5	116.67 (11)	C12—C13—C14	117.48 (13)
C9—C4—C5	122.11 (12)	C12—C13—C16	121.51 (15)
C6—C5—C4	118.67 (12)	C14—C13—C16	121.00 (15)
C6—C5—H5	120.7	C15—C14—C13	121.28 (14)
C4—C5—H5	120.7	C15—C14—H14	119.4
C5—C6—C7	120.67 (13)	C13—C14—H14	119.4
C5—C6—H6	119.7	C14—C15—C10	121.18 (13)
C7—C6—H6	119.7	C14—C15—H15	119.4
C8—C7—C6	119.77 (13)	C10—C15—H15	119.4
C8—C7—H7	120.1	C13—C16—H16A	109.5
C6—C7—H7	120.1	C13—C16—H16B	109.5
C7—C8—C9	120.98 (12)	H16A—C16—H16B	109.5
C7—C8—H8	119.5	C13—C16—H16C	109.5
C9—C8—H8	119.5	H16A—C16—H16C	109.5
C4—C9—C8	117.77 (12)	H16B—C16—H16C	109.5
O1—C1—C2—C3	177.41 (13)	C7—C8—C9—C1	176.44 (12)
C9—C1—C2—C3	−3.73 (16)	O1—C1—C9—C4	179.50 (12)
O1—C1—C2—C10	−4.05 (19)	C2—C1—C9—C4	0.59 (16)
C9—C1—C2—C10	174.81 (10)	O1—C1—C9—C8	1.32 (18)
C1—C2—C3—O2	3.58 (19)	C2—C1—C9—C8	−177.58 (11)
C10—C2—C3—O2	−175.02 (11)	C3—C2—C10—C15	30.64 (18)
C2—C3—O2—C4	0.20 (19)	C1—C2—C10—C15	−147.90 (13)
C3—O2—C4—C9	−3.63 (17)	C3—C2—C10—C11	−149.10 (13)
C3—O2—C4—C5	176.38 (11)	C1—C2—C10—C11	32.37 (19)
O2—C4—C5—C6	−179.99 (12)	C15—C10—C11—C12	−0.6 (2)
C9—C4—C5—C6	0.01 (19)	C2—C10—C11—C12	179.13 (13)
C4—C5—C6—C7	−1.0 (2)	C10—C11—C12—C13	−0.7 (2)
C5—C6—C7—C8	0.6 (2)	C11—C12—C13—C14	0.7 (2)
C6—C7—C8—C9	0.8 (2)	C11—C12—C13—C16	−179.92 (16)
O2—C4—C9—C8	−178.63 (11)	C12—C13—C14—C15	0.5 (2)
C5—C4—C9—C8	1.36 (18)	C16—C13—C14—C15	−178.87 (15)
O2—C4—C9—C1	3.14 (18)	C13—C14—C15—C10	−1.8 (2)
C5—C4—C9—C1	−176.87 (11)	C11—C10—C15—C14	1.8 (2)
C7—C8—C9—C4	−1.79 (19)	C2—C10—C15—C14	−177.94 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1^i	0.94	2.49	3.4255 (16)	172

Symmetry code: (i) x−1, y, z.