2-Oxo-2H-chromen-4-yl 3,3-di­methyl­butano­ate

In the crystal of the title compound, C₁₅H₁₆O₄, the mol­ecules are connected through C—H...O hydrogen bonds, generating [100] chains, which are crosslinked by weak π–π stacking inter­actions.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.031
• wR factor = 0.084
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.500
           From the CIF: _refine_ls_abs_structure_Flack_su    0.300
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C12 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
                5 18  0,   0  0  2,

Alert level G
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      0.300 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         12 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
                0  0  2,
PLAT915_ALERT_3_G No Flack x Check Done: Low Friedel Pair Coverage         67 %
PLAT916_ALERT_2_G Hooft y and Flack x Parameter Values Differ by .       0.23 Check
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........       4.29 Note
              Predicted wR2: Based on SigI   2  1.96 or SHELX Weight  8.35       
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 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
   7 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

2-Oxo-2H-chromen-4-yl 3,3-dimethylbutanoate

Crystal data

C15H16O4	Dx = 1.283 Mg m^−3
Mr = 260.28	Melting point: 430 K
Orthorhombic, Pna21	Cu Kα radiation, λ = 1.54184 Å
a = 10.6769 (3) Å	Cell parameters from 6044 reflections
b = 17.9611 (5) Å	θ = 4.8–72.4°
c = 7.0266 (2) Å	µ = 0.76 mm^−1
V = 1347.48 (7) Å^3	T = 295 K
Z = 4	Prism, colourless
F(000) = 552	0.32 × 0.18 × 0.16 mm

Data collection

SuperNova, Dual, Cu at home/near, AtlasS2 diffractometer	2133 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tube; SuperNova (Cu) X-ray Source	Rint = 0.020
Mirror monochromator	θmax = 72.4°, θmin = 4.8°
ω scan	h = −12→13
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2023)	k = −22→21
Tmin = 0.829, Tmax = 1.000	l = −8→7
9694 measured reflections	2249 standard reflections every 25 min
2249 independent reflections

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)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.084	w = 1/[σ^2(Fo^2) + (0.049P)^2 + 0.0768P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2249 reflections	Δρmax = 0.11 e Å^−3
176 parameters	Δρmin = −0.13 e Å^−3
1 restraint	Absolute structure: Refined as an inversion twin.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.5 (3)

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.

Refinement. Refined as a 2-component inversion twin.

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

	x	y	z	Uiso*/Ueq
O1	0.81314 (18)	0.29193 (8)	0.4568 (3)	0.0877 (6)
O2	0.62460 (14)	0.33944 (6)	0.4897 (2)	0.0631 (4)
O3	0.76506 (11)	0.55295 (6)	0.5416 (2)	0.0578 (4)
O4	0.93542 (18)	0.52915 (9)	0.7209 (4)	0.0924 (7)
C1	0.72707 (16)	0.47995 (8)	0.5255 (3)	0.0468 (4)
C2	0.80284 (18)	0.42179 (10)	0.5013 (4)	0.0569 (4)
H2	0.8891	0.4290	0.4974	0.068*
C3	0.7522 (2)	0.34755 (10)	0.4809 (3)	0.0615 (5)
C4	0.54603 (17)	0.39958 (9)	0.5092 (3)	0.0504 (4)
C5	0.4183 (2)	0.38581 (12)	0.5105 (3)	0.0650 (5)
H5	0.3882	0.3373	0.5014	0.078*
C6	0.33703 (19)	0.44444 (14)	0.5253 (3)	0.0673 (6)
H6	0.2512	0.4356	0.5262	0.081*
C7	0.38128 (18)	0.51700 (12)	0.5390 (3)	0.0623 (5)
H7	0.3252	0.5565	0.5470	0.075*
C8	0.50808 (17)	0.53037 (10)	0.5406 (3)	0.0515 (4)
H8	0.5375	0.5789	0.5509	0.062*
C9	0.59267 (16)	0.47158 (8)	0.5268 (3)	0.0435 (4)
C10	0.87001 (19)	0.57316 (12)	0.6437 (4)	0.0583 (5)
C11	0.8867 (2)	0.65593 (11)	0.6425 (4)	0.0604 (5)
H11A	0.9275	0.6707	0.7599	0.072*
H11B	0.8046	0.6792	0.6401	0.072*
C12	0.96367 (16)	0.68573 (9)	0.4739 (3)	0.0516 (4)
C13	0.9024 (3)	0.66854 (15)	0.2840 (4)	0.0798 (7)
H13A	0.8958	0.6156	0.2684	0.120*
H13B	0.9523	0.6889	0.1830	0.120*
H13C	0.8203	0.6903	0.2806	0.120*
C14	0.9745 (3)	0.77005 (12)	0.5023 (6)	0.0868 (8)
H14A	0.8922	0.7915	0.5070	0.130*
H14B	1.0204	0.7914	0.3983	0.130*
H14C	1.0175	0.7801	0.6195	0.130*
C15	1.0947 (2)	0.65202 (14)	0.4765 (5)	0.0739 (6)
H15A	1.1348	0.6636	0.5952	0.111*
H15B	1.1430	0.6722	0.3735	0.111*
H15C	1.0889	0.5990	0.4626	0.111*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.1116 (13)	0.0485 (8)	0.1030 (14)	0.0254 (8)	−0.0004 (12)	−0.0058 (9)
O2	0.0819 (9)	0.0344 (6)	0.0732 (10)	−0.0071 (5)	−0.0018 (9)	0.0023 (7)
O3	0.0523 (6)	0.0387 (6)	0.0824 (10)	−0.0079 (5)	−0.0064 (7)	0.0043 (6)
O4	0.0924 (12)	0.0634 (9)	0.1214 (18)	−0.0185 (9)	−0.0473 (12)	0.0232 (10)
C1	0.0538 (9)	0.0364 (8)	0.0503 (10)	−0.0053 (6)	0.0001 (9)	0.0039 (8)
C2	0.0570 (9)	0.0482 (9)	0.0654 (12)	0.0032 (7)	0.0014 (10)	0.0019 (10)
C3	0.0812 (13)	0.0434 (9)	0.0598 (13)	0.0092 (9)	−0.0012 (12)	0.0017 (9)
C4	0.0656 (10)	0.0421 (8)	0.0436 (9)	−0.0100 (7)	−0.0008 (9)	0.0045 (8)
C5	0.0738 (12)	0.0637 (11)	0.0574 (12)	−0.0302 (10)	−0.0038 (11)	0.0092 (11)
C6	0.0533 (10)	0.0923 (15)	0.0563 (12)	−0.0153 (10)	0.0005 (11)	0.0094 (13)
C7	0.0545 (10)	0.0762 (13)	0.0562 (11)	0.0065 (9)	0.0010 (10)	0.0033 (11)
C8	0.0579 (9)	0.0468 (9)	0.0498 (10)	0.0003 (7)	−0.0009 (9)	0.0014 (8)
C9	0.0527 (8)	0.0381 (7)	0.0397 (8)	−0.0065 (6)	0.0001 (8)	0.0039 (7)
C10	0.0575 (10)	0.0514 (10)	0.0660 (12)	−0.0137 (9)	−0.0017 (10)	0.0029 (10)
C11	0.0597 (11)	0.0497 (10)	0.0716 (13)	−0.0117 (8)	0.0073 (10)	−0.0099 (10)
C12	0.0525 (9)	0.0398 (8)	0.0626 (12)	−0.0086 (7)	−0.0034 (9)	−0.0019 (8)
C13	0.0913 (17)	0.0747 (16)	0.0733 (16)	−0.0182 (13)	−0.0236 (13)	0.0109 (13)
C14	0.1012 (16)	0.0441 (10)	0.115 (2)	−0.0192 (10)	0.0060 (19)	−0.0045 (14)
C15	0.0576 (11)	0.0847 (14)	0.0793 (16)	−0.0015 (10)	0.0018 (12)	−0.0032 (13)

Geometric parameters (Å, º)

O1—C3	1.204 (2)	C8—C9	1.393 (2)
O2—C3	1.371 (3)	C8—H8	0.9300
O2—C4	1.374 (2)	C10—C11	1.497 (3)
O3—C1	1.3771 (19)	C11—C12	1.538 (3)
O3—C10	1.379 (2)	C11—H11A	0.9700
O4—C10	1.186 (3)	C11—H11B	0.9700
C1—C2	1.332 (2)	C12—C13	1.518 (3)
C1—C9	1.443 (2)	C12—C15	1.525 (3)
C2—C3	1.446 (3)	C12—C14	1.532 (3)
C2—H2	0.9300	C13—H13A	0.9600
C4—C5	1.386 (3)	C13—H13B	0.9600
C4—C9	1.391 (2)	C13—H13C	0.9600
C5—C6	1.368 (3)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—C7	1.390 (3)	C14—H14C	0.9600
C6—H6	0.9300	C15—H15A	0.9600
C7—C8	1.375 (3)	C15—H15B	0.9600
C7—H7	0.9300	C15—H15C	0.9600
C3—O2—C4	121.82 (13)	O3—C10—C11	110.79 (18)
C1—O3—C10	122.19 (15)	C10—C11—C12	114.42 (18)
C2—C1—O3	125.33 (16)	C10—C11—H11A	108.7
C2—C1—C9	121.53 (15)	C12—C11—H11A	108.7
O3—C1—C9	113.06 (14)	C10—C11—H11B	108.7
C1—C2—C3	120.57 (18)	C12—C11—H11B	108.7
C1—C2—H2	119.7	H11A—C11—H11B	107.6
C3—C2—H2	119.7	C13—C12—C15	109.0 (2)
O1—C3—O2	117.08 (19)	C13—C12—C14	110.4 (2)
O1—C3—C2	125.2 (2)	C15—C12—C14	108.79 (17)
O2—C3—C2	117.71 (16)	C13—C12—C11	112.06 (17)
O2—C4—C5	117.45 (16)	C15—C12—C11	110.08 (19)
O2—C4—C9	121.39 (16)	C14—C12—C11	106.50 (19)
C5—C4—C9	121.16 (18)	C12—C13—H13A	109.5
C6—C5—C4	119.15 (18)	C12—C13—H13B	109.5
C6—C5—H5	120.4	H13A—C13—H13B	109.5
C4—C5—H5	120.4	C12—C13—H13C	109.5
C5—C6—C7	120.76 (18)	H13A—C13—H13C	109.5
C5—C6—H6	119.6	H13B—C13—H13C	109.5
C7—C6—H6	119.6	C12—C14—H14A	109.5
C8—C7—C6	119.95 (19)	C12—C14—H14B	109.5
C8—C7—H7	120.0	H14A—C14—H14B	109.5
C6—C7—H7	120.0	C12—C14—H14C	109.5
C7—C8—C9	120.36 (17)	H14A—C14—H14C	109.5
C7—C8—H8	119.8	H14B—C14—H14C	109.5
C9—C8—H8	119.8	C12—C15—H15A	109.5
C4—C9—C8	118.61 (16)	C12—C15—H15B	109.5
C4—C9—C1	116.89 (15)	H15A—C15—H15B	109.5
C8—C9—C1	124.49 (15)	C12—C15—H15C	109.5
O4—C10—O3	122.75 (19)	H15A—C15—H15C	109.5
O4—C10—C11	126.5 (2)	H15B—C15—H15C	109.5
C10—O3—C1—C2	−40.0 (3)	C5—C4—C9—C8	−1.7 (3)
C10—O3—C1—C9	143.23 (18)	O2—C4—C9—C1	−0.6 (3)
O3—C1—C2—C3	−178.33 (19)	C5—C4—C9—C1	179.5 (2)
C9—C1—C2—C3	−1.8 (3)	C7—C8—C9—C4	0.7 (3)
C4—O2—C3—O1	−177.4 (2)	C7—C8—C9—C1	179.4 (2)
C4—O2—C3—C2	2.6 (3)	C2—C1—C9—C4	2.5 (3)
C1—C2—C3—O1	179.2 (2)	O3—C1—C9—C4	179.41 (17)
C1—C2—C3—O2	−0.7 (3)	C2—C1—C9—C8	−176.2 (2)
C3—O2—C4—C5	178.0 (2)	O3—C1—C9—C8	0.7 (3)
C3—O2—C4—C9	−1.9 (3)	C1—O3—C10—O4	1.4 (4)
O2—C4—C5—C6	−178.5 (2)	C1—O3—C10—C11	−178.15 (18)
C9—C4—C5—C6	1.4 (3)	O4—C10—C11—C12	91.9 (3)
C4—C5—C6—C7	0.0 (4)	O3—C10—C11—C12	−88.6 (2)
C5—C6—C7—C8	−1.0 (4)	C10—C11—C12—C13	61.4 (2)
C6—C7—C8—C9	0.6 (3)	C10—C11—C12—C15	−60.0 (2)
O2—C4—C9—C8	178.16 (18)	C10—C11—C12—C14	−177.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4	0.93	2.44	2.847 (3)	107
C5—H5···O1^i	0.93	2.48	3.405 (2)	176

Symmetry code: (i) x−1/2, −y+1/2, z.