2-Oxo-2H-chromen-3-yl 4-tert-butyl­benzoate

In the title coumarin derivative, C₂₀H₁₈O₄, the benzene ring of the benzoate group is oriented at a dihedral angle of 57.55 (9)° with respect to the planar chromene ring system [maximum deviation from plane is 0.027 (2) Å]. In the crystal, inversion-related mol­ecules are linked into dimers via C—H...O hydrogen bonds, generating R₂²(12) loops. The dimers are linked by further C—H...O hydrogen bonds forming layers, parallel to the bc plane, which are linked via C—H...π inter­actions, forming a three-dimensional framework

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.048
• wR factor = 0.127
• Data-to-parameter ratio = 10.4

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C17 Check
PLAT761_ALERT_1_C CIF Contains no X-H Bonds ......................     Please Check
PLAT762_ALERT_1_C CIF Contains no X-Y-H or H-Y-H Angles ..........     Please Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      5.222 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          4 Report

Alert level G
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         18 Note
PLAT933_ALERT_2_G Number of OMIT records in Embedded RES .........          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           4 Note

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

   2 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
   2 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: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

2-Oxo-2H-chromen-3-yl 4-tert-butylbenzoate

Crystal data

C20H18O4	Dx = 1.300 Mg m^−3
Mr = 322.34	Melting point: 413 K
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 22.8977 (5) Å	Cell parameters from 11432 reflections
b = 5.9947 (1) Å	θ = 5.2–68.2°
c = 24.0352 (7) Å	µ = 0.09 mm^−1
β = 93.297 (2)°	T = 298 K
V = 3293.73 (13) Å^3	Prism, colorless
Z = 8	0.36 × 0.16 × 0.03 mm
F(000) = 1360

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector	3005 independent reflections
Radiation source: sealed X-ray tube	2740 reflections with I > 2σ(I)
Detector resolution: 5.3048 pixels mm^-1	Rint = 0.031
ω scans	θmax = 25.4°, θmin = 1.7°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −27→27
Tmin = 0.668, Tmax = 1.000	k = −7→7
19994 measured reflections	l = −28→28

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	All H-atom parameters refined
wR(F^2) = 0.127	w = 1/[σ^2(Fo^2) + (0.0332P)^2 + 4.6284P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max = 0.008
3005 reflections	Δρmax = 0.21 e Å^−3
290 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0015 (2)

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
H16	0.3272 (10)	1.023 (4)	0.2757 (10)	0.062 (7)*
H5	0.2542 (10)	0.138 (4)	0.1680 (10)	0.065 (7)*
H9	0.1764 (11)	−0.075 (5)	0.1146 (11)	0.070 (8)*
H13	0.4819 (12)	0.528 (5)	0.3157 (11)	0.075 (8)*
H12	0.4071 (11)	0.422 (5)	0.2516 (10)	0.070 (8)*
H15	0.3990 (11)	1.118 (5)	0.3411 (11)	0.073 (8)*
H7	0.1090 (12)	0.155 (5)	−0.0363 (12)	0.084 (9)*
H6	0.1705 (12)	0.474 (5)	−0.0253 (12)	0.079 (9)*
H18B	0.5169 (14)	1.105 (5)	0.4499 (13)	0.098 (10)*
H18C	0.4654 (15)	1.217 (6)	0.4040 (15)	0.114 (12)*
H18A	0.4507 (14)	0.979 (6)	0.4427 (13)	0.098 (10)*
H19C	0.5502 (14)	0.619 (6)	0.3749 (13)	0.091 (11)*
H19B	0.5623 (15)	0.762 (5)	0.4318 (13)	0.100 (10)*
H20A	0.5254 (15)	1.161 (6)	0.3205 (14)	0.107 (12)*
H8	0.1130 (12)	−0.124 (5)	0.0327 (11)	0.084 (9)*
H20B	0.5787 (14)	1.082 (6)	0.3666 (13)	0.098 (10)*
H20C	0.5607 (15)	0.933 (6)	0.3108 (15)	0.115 (12)*
H19A	0.5026 (19)	0.623 (7)	0.4250 (17)	0.137 (16)*
O1	0.24340 (7)	0.5617 (3)	0.05360 (6)	0.0546 (4)
O2	0.32331 (7)	0.4732 (3)	0.18668 (6)	0.0531 (4)
O3	0.26552 (6)	0.7562 (3)	0.21178 (6)	0.0538 (4)
C1	0.28335 (9)	0.4315 (4)	0.14183 (9)	0.0478 (5)
C12	0.40656 (10)	0.5701 (4)	0.27018 (10)	0.0533 (6)
C10	0.31100 (9)	0.6565 (4)	0.21793 (9)	0.0459 (5)
O4	0.31340 (8)	0.7596 (3)	0.09731 (7)	0.0700 (5)
C5	0.25118 (10)	0.2475 (4)	0.13885 (9)	0.0489 (5)
C2	0.28268 (10)	0.5978 (4)	0.09770 (9)	0.0515 (5)
C11	0.35955 (9)	0.7120 (3)	0.25861 (8)	0.0434 (5)
C3	0.20823 (9)	0.3749 (4)	0.05008 (9)	0.0469 (5)
C17	0.50185 (10)	0.9101 (4)	0.37556 (10)	0.0537 (6)
C14	0.45086 (9)	0.8370 (4)	0.33559 (9)	0.0459 (5)
C4	0.21134 (9)	0.2126 (4)	0.09126 (9)	0.0471 (5)
C15	0.40346 (10)	0.9760 (4)	0.32324 (10)	0.0528 (6)
C16	0.35827 (10)	0.9159 (4)	0.28567 (10)	0.0503 (5)
C9	0.17480 (11)	0.0272 (4)	0.08422 (11)	0.0591 (6)
C13	0.45114 (10)	0.6337 (4)	0.30808 (10)	0.0555 (6)
C6	0.17062 (11)	0.3582 (5)	0.00291 (10)	0.0571 (6)
C8	0.13727 (12)	0.0079 (5)	0.03776 (12)	0.0682 (7)
C7	0.13535 (11)	0.1724 (5)	−0.00266 (12)	0.0652 (7)
C18	0.48124 (14)	1.0693 (6)	0.42020 (13)	0.0742 (8)
C19	0.53159 (19)	0.7113 (6)	0.4051 (2)	0.0958 (13)
C20	0.54615 (13)	1.0336 (6)	0.34139 (15)	0.0732 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0616 (9)	0.0500 (9)	0.0516 (9)	−0.0052 (7)	−0.0018 (7)	0.0076 (7)
O2	0.0572 (9)	0.0480 (9)	0.0528 (9)	0.0049 (7)	−0.0071 (7)	−0.0049 (7)
O3	0.0465 (8)	0.0524 (9)	0.0619 (10)	0.0016 (7)	−0.0013 (7)	−0.0021 (7)
C1	0.0519 (12)	0.0466 (12)	0.0446 (11)	0.0039 (10)	0.0007 (9)	−0.0020 (9)
C12	0.0625 (14)	0.0410 (12)	0.0557 (13)	0.0067 (10)	−0.0031 (11)	−0.0024 (10)
C10	0.0505 (12)	0.0408 (11)	0.0466 (12)	−0.0021 (10)	0.0045 (9)	0.0047 (9)
O4	0.0749 (11)	0.0620 (11)	0.0725 (12)	−0.0237 (9)	−0.0005 (9)	0.0102 (9)
C5	0.0602 (13)	0.0407 (11)	0.0462 (12)	0.0026 (10)	0.0064 (10)	0.0009 (10)
C2	0.0534 (12)	0.0484 (13)	0.0529 (13)	−0.0040 (10)	0.0044 (10)	0.0019 (10)
C11	0.0452 (11)	0.0396 (11)	0.0457 (11)	−0.0010 (9)	0.0047 (8)	0.0044 (9)
C3	0.0464 (11)	0.0445 (11)	0.0501 (12)	0.0021 (9)	0.0060 (9)	−0.0032 (9)
C17	0.0504 (12)	0.0490 (13)	0.0610 (14)	−0.0030 (10)	−0.0041 (10)	0.0006 (11)
C14	0.0457 (11)	0.0420 (11)	0.0501 (12)	−0.0020 (9)	0.0033 (9)	0.0045 (9)
C4	0.0499 (11)	0.0430 (11)	0.0490 (12)	0.0024 (9)	0.0087 (9)	−0.0037 (9)
C15	0.0519 (12)	0.0396 (12)	0.0664 (15)	0.0014 (10)	−0.0011 (10)	−0.0061 (11)
C16	0.0453 (11)	0.0447 (12)	0.0605 (14)	0.0063 (10)	0.0010 (10)	−0.0017 (10)
C9	0.0669 (15)	0.0502 (14)	0.0609 (15)	−0.0073 (12)	0.0108 (12)	−0.0036 (12)
C13	0.0538 (13)	0.0480 (13)	0.0637 (14)	0.0134 (11)	−0.0056 (11)	−0.0006 (11)
C6	0.0578 (13)	0.0611 (15)	0.0522 (13)	0.0074 (12)	0.0001 (11)	−0.0006 (12)
C8	0.0622 (15)	0.0628 (16)	0.0797 (18)	−0.0136 (13)	0.0050 (13)	−0.0163 (14)
C7	0.0539 (14)	0.0739 (18)	0.0670 (16)	0.0014 (13)	−0.0040 (12)	−0.0140 (14)
C18	0.0690 (17)	0.092 (2)	0.0607 (17)	−0.0081 (17)	0.0006 (14)	−0.0159 (16)
C19	0.095 (3)	0.069 (2)	0.116 (3)	−0.0023 (19)	−0.054 (2)	0.009 (2)
C20	0.0577 (16)	0.079 (2)	0.084 (2)	−0.0149 (15)	0.0134 (15)	−0.0106 (17)

Geometric parameters (Å, º)

O1—C2	1.367 (3)	C3—C4	1.387 (3)
O1—C3	1.379 (3)	C3—C6	1.387 (3)
O2—C10	1.369 (3)	C17—C19	1.527 (4)
O2—C1	1.396 (2)	C17—C18	1.531 (4)
O3—C10	1.203 (2)	C17—C20	1.532 (4)
C1—C5	1.326 (3)	C17—C14	1.532 (3)
C1—C2	1.455 (3)	C14—C15	1.387 (3)
C12—C13	1.382 (3)	C14—C13	1.387 (3)
C12—C11	1.387 (3)	C4—C9	1.396 (3)
C10—C11	1.476 (3)	C15—C16	1.381 (3)
O4—C2	1.198 (3)	C9—C8	1.374 (4)
C5—C4	1.437 (3)	C6—C7	1.378 (4)
C11—C16	1.386 (3)	C8—C7	1.383 (4)
C2—O1—C3	122.13 (17)	C19—C17—C18	108.0 (3)
C10—O2—C1	114.90 (16)	C19—C17—C20	109.6 (3)
C5—C1—O2	121.9 (2)	C18—C17—C20	108.3 (2)
C5—C1—C2	123.2 (2)	C19—C17—C14	111.8 (2)
O2—C1—C2	114.77 (19)	C18—C17—C14	111.3 (2)
C13—C12—C11	119.9 (2)	C20—C17—C14	107.8 (2)
O3—C10—O2	122.38 (19)	C15—C14—C13	116.8 (2)
O3—C10—C11	125.7 (2)	C15—C14—C17	121.4 (2)
O2—C10—C11	111.92 (18)	C13—C14—C17	121.73 (19)
C1—C5—C4	119.3 (2)	C3—C4—C9	117.8 (2)
O4—C2—O1	118.8 (2)	C3—C4—C5	118.1 (2)
O4—C2—C1	125.4 (2)	C9—C4—C5	124.1 (2)
O1—C2—C1	115.80 (19)	C16—C15—C14	122.1 (2)
C16—C11—C12	118.9 (2)	C15—C16—C11	120.1 (2)
C16—C11—C10	118.31 (19)	C8—C9—C4	120.5 (3)
C12—C11—C10	122.8 (2)	C12—C13—C14	122.2 (2)
O1—C3—C4	121.33 (19)	C7—C6—C3	118.1 (2)
O1—C3—C6	116.2 (2)	C9—C8—C7	120.3 (3)
C4—C3—C6	122.5 (2)	C6—C7—C8	120.9 (2)

Hydrogen-bond geometry (Å, º)

Cg3 is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3^i	0.96 (3)	2.52 (3)	3.433 (3)	158 (2)
C6—H6···O4^ii	0.97 (3)	2.40 (3)	3.360 (3)	170 (2)
C16—H16···O3^iii	0.98 (2)	2.57 (2)	3.495 (3)	157.1 (19)
C20—H20C···Cg3^iv	1.02 (4)	2.91 (4)	3.892 (4)	162 (3)

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