2-Oxo-2H-chromen-4-yl 4-tert-butyl-benzoate.

In the title mol-ecule, C(20)H(18)O(4), the three methyl groups of the tert-butyl substituent show rotational disorder. Each methyl group is split over three positions, with refined site-occupation factors of 0.711 (4), 0.146 (3) and 0.144 (4). The benzene ring of the benzoate group is oriented at a dihedral angle of 60.70 (7)° with respect to the planar chromene ring [maximum deviation = 0.046 (2) Å]. The crystal structure features centrosymmetric R(2) (2)(8) dimers formed via C-H⋯O inter-actions, and these dimeric aggregates are connected by C-H⋯π inter-actions.

Related literature

For the biological activities of coumarin derivatives, see: Ukhov et al. (2001 ▶); Abd Elhafez et al. (2003 ▶); Basanagouda et al. (2009 ▶); Liu et al. (2008 ▶); Trapkov et al. (1996 ▶); Vukovic et al. (2010 ▶); Emmanuel-Giota et al. (2001 ▶); Hamdi & Dixneuf (2007 ▶); Wang et al. (2001 ▶); Marchenko et al. (2006 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C20H18O4

M = 322.34

Triclinic,

a = 6.4319 (2) Å

b = 9.3498 (3) Å

c = 14.5505 (5) Å

α = 98.481 (1)°

β = 93.655 (1)°

γ = 102.359 (2)°

V = 841.27 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.50 × 0.30 × 0.14 mm

Data collection

Nonius KappaCCD diffractometer

11164 measured reflections

4198 independent reflections

2926 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.157

S = 1.05

4198 reflections

247 parameters

10 restraints

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.16 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97, publCIF (Westrip, 2010 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681200298X/bh2408sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200298X/bh2408Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681200298X/bh2408Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H18O4	Z = 2
Mr = 322.34	F(000) = 340
Triclinic, P1	Dx = 1.273 Mg m−3
Hall symbol: -P 1	Melting point = 381–383 K
a = 6.4319 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3498 (3) Å	Cell parameters from 11164 reflections
c = 14.5505 (5) Å	θ = 2.8–29.0°
α = 98.481 (1)°	µ = 0.09 mm−1
β = 93.655 (1)°	T = 298 K
γ = 102.359 (2)°	Parallelepiped, colourless
V = 841.27 (5) Å3	0.50 × 0.30 × 0.14 mm

Nonius KappaCCD diffractometer	2926 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
graphite	θmax = 29.0°, θmin = 2.8°
φ and ω scans	h = −8→8
11164 measured reflections	k = −12→12
4198 independent reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0589P)2 + 0.1855P] where P = (Fo2 + 2Fc2)/3
4198 reflections	(Δ/σ)max < 0.001
247 parameters	Δρmax = 0.18 e Å−3
10 restraints	Δρmin = −0.16 e Å−3
108 constraints

Refinement. In the title coumpound, the tert-butyl group may rotate virtually freely at least at room temperature, and in the spatial average one sees this group as a rotational toroid. Since it is hard to describe this situation to the refinement program, we have reduced the problem to a refinement of only three sites per methyl group (see Refinement section). The low Ueq as compared to neighbors for atom C17 is caused by this disorder.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.44961 (18)	1.29961 (11)	0.47812 (8)	0.0616 (3)
C14	0.3413 (2)	0.39183 (15)	0.12787 (10)	0.0501 (3)
O3	0.41921 (18)	0.87715 (12)	0.33682 (9)	0.0691 (4)
O2	0.1580 (2)	1.22217 (14)	0.54429 (9)	0.0740 (4)
C4	0.6027 (2)	1.13127 (16)	0.37549 (10)	0.0534 (4)
C12	0.4620 (3)	0.60660 (18)	0.24953 (12)	0.0651 (5)
H12	0.5638	0.6592	0.2978	0.078*
O4	0.1052 (2)	0.85839 (15)	0.25363 (10)	0.0838 (4)
C5	0.6076 (3)	1.27317 (17)	0.42286 (11)	0.0545 (4)
C11	0.2870 (2)	0.66128 (15)	0.22615 (10)	0.0497 (3)
C16	0.1363 (3)	0.57977 (18)	0.15545 (12)	0.0623 (4)
H16	0.0149	0.6138	0.1402	0.075*
C13	0.4863 (3)	0.47264 (18)	0.20086 (12)	0.0671 (5)
H13	0.6042	0.4362	0.2180	0.080*
C2	0.2658 (3)	1.04280 (16)	0.43723 (12)	0.0590 (4)
H2	0.1486	0.9663	0.4403	0.071*
C10	0.2528 (3)	0.80567 (16)	0.27141 (11)	0.0537 (4)
C17	0.3724 (3)	0.24640 (16)	0.07275 (11)	0.0551 (4)
C15	0.1651 (3)	0.44763 (18)	0.10713 (12)	0.0628 (4)
H15	0.0626	0.3948	0.0592	0.075*
C6	0.7699 (3)	1.39340 (19)	0.41635 (13)	0.0679 (5)
H6	0.7691	1.4877	0.4473	0.081*
C3	0.4194 (2)	1.01742 (16)	0.38416 (11)	0.0550 (4)
C9	0.7722 (3)	1.1114 (2)	0.32308 (12)	0.0681 (5)
H9	0.7745	1.0176	0.2919	0.082*
C1	0.2803 (3)	1.18853 (17)	0.49010 (12)	0.0575 (4)
C8	0.9354 (3)	1.2308 (3)	0.31767 (14)	0.0803 (6)
H8	1.0485	1.2174	0.2831	0.096*
C7	0.9322 (3)	1.3711 (2)	0.36341 (15)	0.0780 (5)
H7	1.0420	1.4513	0.3581	0.094*
C18A	0.2652 (7)	0.2152 (4)	−0.0279 (2)	0.0881 (11)	0.711 (4)
H18A	0.3211	0.2965	−0.0593	0.132*	0.711 (4)
H18B	0.1135	0.2042	−0.0269	0.132*	0.711 (4)
H18C	0.2940	0.1256	−0.0604	0.132*	0.711 (4)
C19A	0.6141 (5)	0.2536 (4)	0.0647 (3)	0.0893 (11)	0.711 (4)
H19A	0.6306	0.1656	0.0255	0.134*	0.711 (4)
H19B	0.6857	0.2605	0.1257	0.134*	0.711 (4)
H19C	0.6752	0.3392	0.0381	0.134*	0.711 (4)
C20A	0.2862 (7)	0.1213 (3)	0.1233 (2)	0.0839 (10)	0.711 (4)
H20A	0.1356	0.1128	0.1267	0.126*	0.711 (4)
H20B	0.3579	0.1406	0.1852	0.126*	0.711 (4)
H20C	0.3098	0.0303	0.0902	0.126*	0.711 (4)
C18B	0.392 (4)	0.266 (2)	−0.0247 (12)	0.0881 (11)	0.144 (4)
H18D	0.5084	0.3477	−0.0275	0.132*	0.144 (4)
H18E	0.2615	0.2846	−0.0508	0.132*	0.144 (4)
H18F	0.4180	0.1769	−0.0597	0.132*	0.144 (4)
C19B	0.554 (3)	0.190 (2)	0.1180 (13)	0.0893 (11)	0.144 (4)
H19D	0.5548	0.0926	0.0857	0.134*	0.144 (4)
H19E	0.5330	0.1849	0.1823	0.134*	0.144 (4)
H19F	0.6884	0.2563	0.1144	0.134*	0.144 (4)
C20B	0.154 (3)	0.1210 (15)	0.0767 (14)	0.0839 (10)	0.144 (4)
H20D	0.0333	0.1525	0.0515	0.126*	0.144 (4)
H20E	0.1378	0.1083	0.1403	0.126*	0.144 (4)
H20F	0.1639	0.0284	0.0406	0.126*	0.144 (4)
C18C	0.512 (3)	0.2889 (16)	0.0029 (10)	0.0881 (11)	0.146 (3)
H18G	0.6459	0.3494	0.0330	0.132*	0.146 (3)
H18H	0.4467	0.3441	−0.0364	0.132*	0.146 (3)
H18I	0.5370	0.2016	−0.0342	0.132*	0.146 (3)
C19C	0.465 (3)	0.1613 (18)	0.1414 (11)	0.0893 (11)	0.146 (3)
H19G	0.4762	0.0664	0.1090	0.134*	0.146 (3)
H19H	0.3729	0.1470	0.1902	0.134*	0.146 (3)
H19I	0.6045	0.2170	0.1681	0.134*	0.146 (3)
C20C	0.151 (3)	0.1494 (14)	0.0290 (12)	0.0839 (10)	0.146 (3)
H20G	0.0924	0.1971	−0.0174	0.126*	0.146 (3)
H20H	0.0553	0.1377	0.0769	0.126*	0.146 (3)
H20I	0.1671	0.0537	0.0004	0.126*	0.146 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0675 (7)	0.0415 (5)	0.0719 (7)	0.0107 (5)	0.0124 (5)	−0.0031 (5)
C14	0.0553 (8)	0.0396 (7)	0.0530 (8)	0.0100 (6)	0.0031 (6)	0.0018 (6)
O3	0.0669 (7)	0.0466 (6)	0.0872 (8)	0.0212 (5)	−0.0081 (6)	−0.0158 (5)
O2	0.0765 (8)	0.0623 (7)	0.0795 (8)	0.0150 (6)	0.0226 (6)	−0.0061 (6)
C4	0.0596 (9)	0.0490 (8)	0.0510 (8)	0.0159 (6)	0.0010 (6)	0.0033 (6)
C12	0.0680 (10)	0.0546 (9)	0.0662 (10)	0.0222 (7)	−0.0162 (8)	−0.0138 (7)
O4	0.0957 (10)	0.0718 (8)	0.0843 (9)	0.0461 (7)	−0.0186 (7)	−0.0141 (7)
C5	0.0616 (9)	0.0469 (8)	0.0546 (8)	0.0136 (6)	0.0032 (7)	0.0064 (6)
C11	0.0569 (8)	0.0403 (7)	0.0510 (8)	0.0121 (6)	0.0050 (6)	0.0031 (6)
C16	0.0559 (9)	0.0595 (9)	0.0694 (10)	0.0220 (7)	−0.0057 (7)	−0.0043 (8)
C13	0.0699 (10)	0.0575 (9)	0.0706 (11)	0.0294 (8)	−0.0168 (8)	−0.0114 (8)
C2	0.0608 (9)	0.0419 (7)	0.0707 (10)	0.0101 (6)	0.0048 (7)	0.0005 (7)
C10	0.0614 (9)	0.0450 (7)	0.0553 (8)	0.0173 (6)	0.0038 (7)	0.0032 (6)
C17	0.0630 (9)	0.0433 (7)	0.0565 (9)	0.0141 (6)	0.0046 (7)	−0.0024 (6)
C15	0.0551 (9)	0.0557 (9)	0.0695 (10)	0.0136 (7)	−0.0081 (7)	−0.0111 (7)
C6	0.0731 (11)	0.0516 (9)	0.0747 (11)	0.0062 (8)	0.0028 (9)	0.0102 (8)
C3	0.0611 (9)	0.0405 (7)	0.0608 (9)	0.0165 (6)	−0.0026 (7)	−0.0036 (6)
C9	0.0693 (10)	0.0744 (11)	0.0607 (10)	0.0247 (9)	0.0060 (8)	−0.0002 (8)
C1	0.0621 (9)	0.0469 (8)	0.0610 (9)	0.0134 (7)	0.0050 (7)	0.0001 (7)
C8	0.0673 (11)	0.1024 (16)	0.0702 (12)	0.0151 (10)	0.0156 (9)	0.0135 (11)
C7	0.0711 (11)	0.0790 (13)	0.0798 (12)	0.0017 (9)	0.0084 (9)	0.0219 (10)
C18A	0.122 (3)	0.077 (2)	0.0622 (15)	0.044 (2)	−0.0175 (19)	−0.0209 (14)
C19A	0.0668 (16)	0.084 (2)	0.106 (3)	0.0231 (15)	0.0170 (16)	−0.0296 (18)
C20A	0.125 (3)	0.0432 (11)	0.086 (2)	0.0221 (15)	0.0319 (19)	0.0047 (13)
C18B	0.122 (3)	0.077 (2)	0.0622 (15)	0.044 (2)	−0.0175 (19)	−0.0209 (14)
C19B	0.0668 (16)	0.084 (2)	0.106 (3)	0.0231 (15)	0.0170 (16)	−0.0296 (18)
C20B	0.125 (3)	0.0432 (11)	0.086 (2)	0.0221 (15)	0.0319 (19)	0.0047 (13)
C18C	0.122 (3)	0.077 (2)	0.0622 (15)	0.044 (2)	−0.0175 (19)	−0.0209 (14)
C19C	0.0668 (16)	0.084 (2)	0.106 (3)	0.0231 (15)	0.0170 (16)	−0.0296 (18)
C20C	0.125 (3)	0.0432 (11)	0.086 (2)	0.0221 (15)	0.0319 (19)	0.0047 (13)

O1—C1	1.374 (2)	C6—C7	1.369 (3)
O1—C5	1.3760 (19)	C6—H6	0.9300
C14—C15	1.380 (2)	C9—C8	1.375 (3)
C14—C13	1.380 (2)	C9—H9	0.9300
C14—C17	1.5322 (19)	C8—C7	1.385 (3)
O3—C10	1.3691 (19)	C8—H8	0.9300
O3—C3	1.3883 (17)	C7—H7	0.9300
O2—C1	1.2048 (19)	C18A—H18A	0.9600
C4—C5	1.395 (2)	C18A—H18B	0.9600
C4—C9	1.398 (2)	C18A—H18C	0.9600
C4—C3	1.435 (2)	C19A—H19A	0.9600
C12—C11	1.376 (2)	C19A—H19B	0.9600
C12—C13	1.390 (2)	C19A—H19C	0.9600
C12—H12	0.9300	C20A—H20A	0.9600
O4—C10	1.1906 (18)	C20A—H20B	0.9600
C5—C6	1.380 (2)	C20A—H20C	0.9600
C11—C16	1.380 (2)	C18B—H18D	0.9600
C11—C10	1.4792 (19)	C18B—H18E	0.9600
C16—C15	1.383 (2)	C18B—H18F	0.9600
C16—H16	0.9300	C19B—H19D	0.9600
C13—H13	0.9300	C19B—H19E	0.9600
C2—C3	1.331 (2)	C19B—H19F	0.9600
C2—C1	1.444 (2)	C20B—H20D	0.9600
C2—H2	0.9300	C20B—H20E	0.9600
C17—C18C	1.442 (16)	C20B—H20F	0.9600
C17—C18B	1.465 (17)	C18C—H18G	0.9600
C17—C20A	1.498 (3)	C18C—H18H	0.9600
C17—C19C	1.533 (17)	C18C—H18I	0.9600
C17—C19B	1.533 (16)	C19C—H19G	0.9600
C17—C18A	1.538 (3)	C19C—H19H	0.9600
C17—C19A	1.554 (3)	C19C—H19I	0.9600
C17—C20C	1.557 (16)	C20C—H20G	0.9600
C17—C20B	1.634 (17)	C20C—H20H	0.9600
C15—H15	0.9300	C20C—H20I	0.9600
C1—O1—C5	122.13 (12)	C14—C17—C20B	106.5 (5)
C15—C14—C13	116.78 (13)	C19C—C17—C20B	82.4 (9)
C15—C14—C17	121.34 (13)	C19B—C17—C20B	105.6 (8)
C13—C14—C17	121.88 (13)	C18A—C17—C20B	76.5 (7)
C10—O3—C3	119.42 (12)	C19A—C17—C20B	138.2 (6)
C5—C4—C9	118.27 (15)	C14—C15—C16	121.97 (14)
C5—C4—C3	116.26 (14)	C14—C15—H15	119.0
C9—C4—C3	125.47 (15)	C16—C15—H15	119.0
C11—C12—C13	119.84 (14)	C7—C6—C5	118.66 (17)
C11—C12—H12	120.1	C7—C6—H6	120.7
C13—C12—H12	120.1	C5—C6—H6	120.7
O1—C5—C6	116.91 (14)	C2—C3—O3	122.37 (15)
O1—C5—C4	121.30 (14)	C2—C3—C4	122.51 (14)
C6—C5—C4	121.79 (16)	O3—C3—C4	115.05 (14)
C12—C11—C16	118.93 (13)	C8—C9—C4	119.91 (18)
C12—C11—C10	123.52 (14)	C8—C9—H9	120.0
C16—C11—C10	117.54 (13)	C4—C9—H9	120.0
C11—C16—C15	120.26 (14)	O2—C1—O1	116.63 (14)
C11—C16—H16	119.9	O2—C1—C2	126.09 (16)
C15—C16—H16	119.9	O1—C1—C2	117.28 (14)
C14—C13—C12	122.17 (14)	C9—C8—C7	120.33 (18)
C14—C13—H13	118.9	C9—C8—H8	119.8
C12—C13—H13	118.9	C7—C8—H8	119.8
C3—C2—C1	120.32 (15)	C6—C7—C8	121.00 (18)
C3—C2—H2	119.8	C6—C7—H7	119.5
C1—C2—H2	119.8	C8—C7—H7	119.5
O4—C10—O3	122.60 (14)	C17—C18A—H18A	109.5
O4—C10—C11	126.25 (15)	C17—C18A—H18B	109.5
O3—C10—C11	111.12 (12)	C17—C18A—H18C	109.5
C18C—C17—C20A	143.4 (6)	C17—C19A—H19A	109.5
C18B—C17—C20A	136.4 (7)	C17—C19A—H19B	109.5
C18C—C17—C14	105.8 (5)	C17—C19A—H19C	109.5
C18B—C17—C14	108.4 (6)	C17—C20A—H20A	109.5
C20A—C17—C14	109.06 (15)	C17—C20A—H20B	109.5
C18C—C17—C19C	113.7 (8)	C17—C20A—H20C	109.5
C18B—C17—C19C	136.7 (8)	C17—C18B—H18D	109.5
C14—C17—C19C	108.2 (5)	C17—C18B—H18E	109.5
C18C—C17—C19B	87.6 (9)	H18D—C18B—H18E	109.5
C18B—C17—C19B	114.8 (8)	C17—C18B—H18F	109.5
C20A—C17—C19B	69.0 (8)	H18D—C18B—H18F	109.5
C14—C17—C19B	112.8 (5)	H18E—C18B—H18F	109.5
C18C—C17—C18A	64.7 (7)	C17—C19B—H19D	109.5
C20A—C17—C18A	110.4 (2)	C17—C19B—H19E	109.5
C14—C17—C18A	112.45 (16)	H19D—C19B—H19E	109.5
C19C—C17—C18A	138.0 (5)	C17—C19B—H19F	109.5
C19B—C17—C18A	131.7 (6)	H19D—C19B—H19F	109.5
C18C—C17—C19A	47.3 (7)	H19E—C19B—H19F	109.5
C18B—C17—C19A	78.1 (9)	C17—C20B—H20D	109.5
C20A—C17—C19A	108.4 (2)	C17—C20B—H20E	109.5
C14—C17—C19A	110.35 (15)	H20D—C20B—H20E	109.5
C19C—C17—C19A	67.9 (7)	C17—C20B—H20F	109.5
C18A—C17—C19A	106.2 (2)	H20D—C20B—H20F	109.5
C18C—C17—C20C	112.4 (7)	H20E—C20B—H20F	109.5
C18B—C17—C20C	81.3 (9)	C17—C18C—H18G	109.5
C20A—C17—C20C	65.9 (6)	C17—C18C—H18H	109.5
C14—C17—C20C	109.1 (5)	C17—C18C—H18I	109.5
C19C—C17—C20C	107.5 (7)	C17—C19C—H19G	109.5
C19B—C17—C20C	125.8 (8)	C17—C19C—H19H	109.5
C18A—C17—C20C	48.9 (7)	C17—C19C—H19I	109.5
C19A—C17—C20C	139.5 (5)	C17—C20C—H20G	109.5
C18C—C17—C20B	136.6 (8)	C17—C20C—H20H	109.5
C18B—C17—C20B	108.4 (8)	C17—C20C—H20I	109.5
C1—O1—C5—C6	−179.82 (15)	C13—C14—C17—C18A	−152.6 (2)
C1—O1—C5—C4	0.4 (2)	C15—C14—C17—C19A	146.2 (2)
C9—C4—C5—O1	−177.87 (14)	C13—C14—C17—C19A	−34.3 (3)
C3—C4—C5—O1	2.9 (2)	C15—C14—C17—C20C	−24.5 (7)
C9—C4—C5—C6	2.4 (2)	C13—C14—C17—C20C	155.0 (7)
C3—C4—C5—C6	−176.80 (15)	C15—C14—C17—C20B	−54.0 (9)
C13—C12—C11—C16	1.2 (3)	C13—C14—C17—C20B	125.5 (9)
C13—C12—C11—C10	−177.33 (16)	C13—C14—C15—C16	1.4 (3)
C12—C11—C16—C15	−2.0 (3)	C17—C14—C15—C16	−179.10 (16)
C10—C11—C16—C15	176.59 (16)	C11—C16—C15—C14	0.7 (3)
C15—C14—C13—C12	−2.2 (3)	O1—C5—C6—C7	178.80 (16)
C17—C14—C13—C12	178.25 (17)	C4—C5—C6—C7	−1.4 (3)
C11—C12—C13—C14	1.0 (3)	C1—C2—C3—O3	175.81 (15)
C3—O3—C10—O4	−0.7 (3)	C1—C2—C3—C4	−0.9 (3)
C3—O3—C10—C11	177.51 (14)	C10—O3—C3—C2	60.6 (2)
C12—C11—C10—O4	179.64 (18)	C10—O3—C3—C4	−122.45 (16)
C16—C11—C10—O4	1.1 (3)	C5—C4—C3—C2	−2.7 (2)
C12—C11—C10—O3	1.5 (2)	C9—C4—C3—C2	178.21 (16)
C16—C11—C10—O3	−177.09 (14)	C5—C4—C3—O3	−179.61 (13)
C15—C14—C17—C18C	96.6 (8)	C9—C4—C3—O3	1.3 (2)
C13—C14—C17—C18C	−83.9 (8)	C5—C4—C9—C8	−1.4 (3)
C15—C14—C17—C18B	62.4 (10)	C3—C4—C9—C8	177.69 (17)
C13—C14—C17—C18B	−118.1 (10)	C5—O1—C1—O2	175.72 (14)
C15—C14—C17—C20A	−94.8 (2)	C5—O1—C1—C2	−4.0 (2)
C13—C14—C17—C20A	84.7 (3)	C3—C2—C1—O2	−175.46 (17)
C15—C14—C17—C19C	−141.2 (7)	C3—C2—C1—O1	4.2 (2)
C13—C14—C17—C19C	38.2 (8)	C4—C9—C8—C7	−0.4 (3)
C15—C14—C17—C19B	−169.4 (10)	C5—C6—C7—C8	−0.5 (3)
C13—C14—C17—C19B	10.1 (10)	C9—C8—C7—C6	1.4 (3)
C15—C14—C17—C18A	27.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2i	0.93	2.39	3.323 (2)	177
C18B—H18D···Cg3ii	0.96	2.83	3.54 (2)	133
C18C—H18I···Cg3ii	0.96	2.90	3.47 (2)	119
C19C—H19I···Cg2iii	0.96	2.95	3.75 (2)	141
C1—O2···Cg2iv	1.205 (2)	3.528 (2)	3.802 (2)	94.68 (11)

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the chromene benzene and benzoate benzene rings.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2i	0.93	2.39	3.323 (2)	177
C18B—H18D⋯Cg3ii	0.96	2.83	3.54 (2)	133
C18C—H18I⋯Cg3ii	0.96	2.90	3.47 (2)	119
C19C—H19I⋯Cg2iii	0.96	2.95	3.75 (2)	141

Symmetry codes: (i) ; (ii) ; (iii) .