Inter­actions in flavanone and chalcone derivatives: Hirshfeld surface analysis, energy frameworks and global reactivity descriptors

The present study examines a series of flavanone and chalcone derivatives substituted with electron-withdrawing groups (Cl or Br) and electron-donating groups (OH, CH₃ and OCH₃), namely, 7-meth­oxy-2-phenyl-3,4-di­hydro-2H-1-benzo­pyran-4-one, C₁₆H₁₄O₃, 2-(4-meth­oxy­phen­yl)-3,4-di­hydro-2H-1-benzo­py­ran-4-one, C₁₆H₁₄O₃, 2-(4-meth­oxy­phen­yl)-6-methyl-3,4-di­hydro-2H-1-benzo­pyran-4-one, C₁₇H₁₆O₃, 2-(4-chloro­phen­yl)-3,4-di­hydro-2H-1-benzo­pyran-4-one, C₁₅H₁₁ClO₂, 8-bromo-6-methyl-2-phenyl-3,4-di­hydro-2H-1-benzo­pyran-4-one, C₁₆H₁₃BrO₂, (2E)-1-(2-hy­droxy­phen­yl)-3-(4-meth­oxy­phen­yl)prop-2-en-1-one, C₁₆H₁₄O₃, and (2E)-1-(2-hy­droxy­phen­yl)-3-(4-hy­droxy­phen­yl)prop-2-en-1-one, C₁₅H₁₂O₃. It com­pares the two groups of derivatives with regard to their inter­molecular inter­actions in the crystal lattice and lattice energy calculations, together with energy framework visualization and global reactivity descriptors (chemical hardness, chemical potential and electrophilicity index). It also discusses the relationships between different noncovalent inter­actions derived from Hirshfeld surface analysis, crystal lattice energy and global reactivity descriptors of the com­pounds.

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015) for FL1, FL2, FL3, FL5, FL8; 'CrysAlis PRO (Rigaku OD, 2015)' for CH2, CH4. Cell refinement: CrysAlis PRO (Rigaku OD, 2015) for FL1, FL2, FL3, FL5, FL8; 'CrysAlis PRO (Rigaku OD, 2015)' for CH2, CH4. Data reduction: CrysAlis PRO (Rigaku OD, 2015) for FL1, FL2, FL3, FL5, FL8; 'CrysAlis PRO (Rigaku OD, 2015)' for CH2, CH4. For all structures, program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) and publCIF (Westrip, 2010).

7-Methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one (FL1)

Crystal data

C16H14O3	F(000) = 536
Mr = 254.27	Dx = 1.286 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.5168 (3) Å	Cell parameters from 5133 reflections
b = 6.6031 (2) Å	θ = 3.5–31.8°
c = 23.3468 (7) Å	µ = 0.09 mm^−1
β = 90.737 (3)°	T = 100 K
V = 1312.85 (7) Å^3	Prism, colourless
Z = 4	0.3 × 0.2 × 0.1 mm

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas detector	2724 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	2550 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.025
Detector resolution: 10.4498 pixels mm^-1	θmax = 26.5°, θmin = 3.2°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −6→8
Tmin = 0.341, Tmax = 1.000	l = −29→29
20587 measured reflections

Refinement

Refinement on F^2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.112	w = 1/[σ^2(Fo^2) + (0.0359P)^2 + 1.1824P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2724 reflections	Δρmax = 0.40 e Å^−3
183 parameters	Δρmin = −0.34 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.

Refinement. Single-crystal X-ray data of five flavanone derivatives (FL1, FL2, FL3, FL5 and FL8) were collected on a micro-focus SuperNova diffractometer with an Atlas detector, whereas data collection of two chalcone derivatives (CH2 and CH4) was carried out on an Xcalibur diffractometer with a Sapphire3 detector; all using Mo Kα and ω scans at a low temperature of 100.0 (1) K. The X-ray data were corrected for absorption using CrysAlis PRO (Agilent, 2015). All structures were solved using SHELXT (Sheldrick, 2015a) and refined with SHELXL2014/7 (Sheldrick, 2015b). All non-H atoms were refined anisotropically.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.60169 (12)	0.27910 (16)	0.39607 (4)	0.0210 (2)
O2	0.18209 (13)	0.31539 (17)	0.52993 (5)	0.0280 (3)
O4	0.45378 (13)	0.80554 (18)	0.31591 (5)	0.0294 (3)
C4	0.49738 (17)	0.6489 (2)	0.33976 (6)	0.0212 (3)
C5	0.42163 (17)	0.5646 (2)	0.39142 (6)	0.0203 (3)
C6	0.29195 (18)	0.6616 (2)	0.41686 (7)	0.0258 (3)
H6	0.2560	0.7870	0.4017	0.031*
C7	0.21647 (18)	0.5783 (2)	0.46319 (7)	0.0251 (3)
H7	0.1303	0.6467	0.4799	0.030*
C8	0.26814 (17)	0.3904 (2)	0.48565 (6)	0.0210 (3)
C9	0.39774 (17)	0.2929 (2)	0.46267 (6)	0.0197 (3)
H9	0.4341	0.1685	0.4783	0.024*
C10	0.47402 (16)	0.3817 (2)	0.41586 (6)	0.0182 (3)
C11	0.2223 (2)	0.1175 (3)	0.55208 (7)	0.0302 (4)
H11A	0.2160	0.0177	0.5211	0.045*
H11B	0.1487	0.0803	0.5823	0.045*
H11C	0.3294	0.1203	0.5679	0.045*
C12	0.8151 (2)	0.2302 (3)	0.33399 (8)	0.0425 (5)
C13	0.9552 (3)	0.2792 (3)	0.36011 (7)	0.0466 (6)
H13	0.9613	0.3919	0.3853	0.056*
C14	1.0867 (2)	0.1648 (3)	0.34967 (8)	0.0425 (5)
H14	1.1836	0.1990	0.3678	0.051*
C15	1.0792 (2)	0.0001 (3)	0.31294 (7)	0.0336 (4)
H15	1.1705	−0.0783	0.3059	0.040*
C16	0.9390 (2)	−0.0489 (3)	0.28685 (7)	0.0340 (4)
H16	0.9326	−0.1618	0.2617	0.041*
C17	0.8079 (2)	0.0660 (3)	0.29730 (8)	0.0389 (5)
H17	0.7110	0.0322	0.2791	0.047*
C2A	0.6423 (3)	0.3149 (4)	0.33685 (12)	0.0185 (9)	0.533 (6)
H2A	0.5724	0.2316	0.3114	0.022*	0.533 (6)
C2B	0.7094 (4)	0.3986 (5)	0.36092 (14)	0.0204 (10)	0.467 (6)
H2B	0.7760	0.4845	0.3868	0.024*	0.467 (6)
C3	0.6349 (2)	0.5275 (3)	0.31836 (8)	0.0344 (4)
H3A	0.6324	0.5306	0.2760	0.041*	0.533 (6)
H3B	0.7328	0.5957	0.3311	0.041*	0.533 (6)
H3C	0.5984	0.4420	0.2860	0.041*	0.467 (6)
H3D	0.7144	0.6224	0.3034	0.041*	0.467 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0214 (5)	0.0215 (5)	0.0203 (5)	0.0050 (4)	0.0059 (4)	0.0030 (4)
O2	0.0289 (6)	0.0270 (6)	0.0284 (6)	0.0058 (5)	0.0132 (5)	0.0071 (5)
O4	0.0283 (6)	0.0288 (6)	0.0311 (6)	0.0065 (5)	0.0048 (5)	0.0113 (5)
C4	0.0203 (7)	0.0223 (7)	0.0208 (7)	0.0010 (6)	−0.0005 (5)	0.0018 (6)
C5	0.0207 (7)	0.0218 (7)	0.0185 (7)	0.0024 (6)	0.0008 (5)	0.0007 (6)
C6	0.0278 (8)	0.0238 (8)	0.0258 (8)	0.0078 (6)	0.0037 (6)	0.0047 (6)
C7	0.0238 (7)	0.0264 (8)	0.0251 (7)	0.0072 (6)	0.0059 (6)	0.0006 (6)
C8	0.0212 (7)	0.0233 (7)	0.0186 (7)	−0.0009 (6)	0.0030 (5)	0.0007 (6)
C9	0.0217 (7)	0.0184 (7)	0.0192 (7)	0.0019 (6)	0.0007 (5)	0.0008 (6)
C10	0.0175 (6)	0.0200 (7)	0.0172 (6)	0.0010 (5)	0.0000 (5)	−0.0032 (5)
C11	0.0379 (9)	0.0242 (8)	0.0290 (8)	0.0010 (7)	0.0125 (7)	0.0060 (7)
C12	0.0480 (11)	0.0427 (11)	0.0374 (10)	0.0269 (9)	0.0279 (9)	0.0241 (9)
C13	0.1000 (18)	0.0214 (8)	0.0187 (8)	−0.0007 (10)	0.0113 (9)	−0.0015 (7)
C14	0.0436 (10)	0.0533 (12)	0.0301 (9)	−0.0232 (10)	−0.0160 (8)	0.0189 (9)
C15	0.0298 (8)	0.0418 (10)	0.0295 (8)	0.0172 (7)	0.0140 (7)	0.0181 (8)
C16	0.0612 (12)	0.0215 (8)	0.0195 (7)	−0.0040 (8)	0.0036 (7)	−0.0014 (6)
C17	0.0246 (8)	0.0529 (12)	0.0391 (10)	−0.0121 (8)	−0.0064 (7)	0.0252 (9)
C2A	0.0202 (15)	0.0208 (15)	0.0147 (14)	0.0021 (12)	0.0037 (11)	0.0004 (11)
C2B	0.0205 (17)	0.0217 (17)	0.0190 (16)	−0.0009 (14)	0.0023 (13)	−0.0021 (13)
C3	0.0339 (9)	0.0373 (10)	0.0324 (9)	0.0134 (8)	0.0162 (7)	0.0155 (8)

Geometric parameters (Å, º)

O1—C10	1.3666 (17)	C12—C17	1.383 (3)
O1—C2A	1.449 (3)	C12—C2B	1.567 (4)
O1—C2B	1.469 (3)	C12—C2A	1.577 (3)
O2—C8	1.3676 (17)	C13—C14	1.376 (3)
O2—C11	1.4448 (19)	C13—H13	0.9500
O4—C4	1.2299 (19)	C14—C15	1.386 (3)
C4—C5	1.483 (2)	C14—H14	0.9500
C4—C3	1.509 (2)	C15—C16	1.372 (3)
C5—C10	1.406 (2)	C15—H15	0.9500
C5—C6	1.414 (2)	C16—C17	1.375 (3)
C6—C7	1.380 (2)	C16—H16	0.9500
C6—H6	0.9500	C17—H17	0.9500
C7—C8	1.415 (2)	C2A—C3	1.470 (3)
C7—H7	0.9500	C2A—H2A	1.0000
C8—C9	1.391 (2)	C2B—C3	1.449 (4)
C9—C10	1.406 (2)	C2B—H2B	1.0000
C9—H9	0.9500	C3—H3A	0.9900
C11—H11A	0.9800	C3—H3B	0.9900
C11—H11B	0.9800	C3—H3C	0.9900
C11—H11C	0.9800	C3—H3D	0.9900
C12—C13	1.372 (3)
C10—O1—C2A	116.25 (14)	C14—C13—H13	120.1
C10—O1—C2B	115.34 (16)	C13—C14—C15	120.63 (17)
C8—O2—C11	118.11 (12)	C13—C14—H14	119.7
O4—C4—C5	123.48 (14)	C15—C14—H14	119.7
O4—C4—C3	121.85 (14)	C16—C15—C14	119.53 (16)
C5—C4—C3	114.67 (13)	C16—C15—H15	120.2
C10—C5—C6	117.64 (13)	C14—C15—H15	120.2
C10—C5—C4	120.87 (13)	C15—C16—C17	119.67 (16)
C6—C5—C4	121.46 (13)	C15—C16—H16	120.2
C7—C6—C5	121.54 (14)	C17—C16—H16	120.2
C7—C6—H6	119.2	C16—C17—C12	120.88 (17)
C5—C6—H6	119.2	C16—C17—H17	119.6
C6—C7—C8	119.62 (14)	C12—C17—H17	119.6
C6—C7—H7	120.2	O1—C2A—C3	115.2 (2)
C8—C7—H7	120.2	O1—C2A—C12	102.52 (18)
O2—C8—C9	124.03 (14)	C3—C2A—C12	111.3 (2)
O2—C8—C7	115.50 (13)	O1—C2A—H2A	109.2
C9—C8—C7	120.47 (13)	C3—C2A—H2A	109.2
C8—C9—C10	118.92 (13)	C12—C2A—H2A	109.2
C8—C9—H9	120.5	C3—C2B—O1	115.3 (2)
C10—C9—H9	120.5	C3—C2B—C12	113.0 (2)
O1—C10—C5	122.58 (13)	O1—C2B—C12	102.1 (2)
O1—C10—C9	115.69 (13)	C3—C2B—H2B	108.7
C5—C10—C9	121.74 (13)	O1—C2B—H2B	108.7
O2—C11—H11A	109.5	C12—C2B—H2B	108.7
O2—C11—H11B	109.5	C2B—C3—C4	114.84 (17)
H11A—C11—H11B	109.5	C2A—C3—C4	116.13 (16)
O2—C11—H11C	109.5	C2A—C3—H3A	108.3
H11A—C11—H11C	109.5	C4—C3—H3A	108.3
H11B—C11—H11C	109.5	C2A—C3—H3B	108.3
C13—C12—C17	119.47 (16)	C4—C3—H3B	108.3
C13—C12—C2B	98.9 (2)	H3A—C3—H3B	107.4
C17—C12—C2B	141.6 (2)	C2B—C3—H3C	108.6
C13—C12—C2A	134.8 (2)	C4—C3—H3C	108.6
C17—C12—C2A	105.7 (2)	C2B—C3—H3D	108.6
C12—C13—C14	119.82 (17)	C4—C3—H3D	108.6
C12—C13—H13	120.1	H3C—C3—H3D	107.5
O4—C4—C5—C10	178.20 (14)	C13—C14—C15—C16	0.0 (3)
C3—C4—C5—C10	−2.2 (2)	C14—C15—C16—C17	0.2 (2)
O4—C4—C5—C6	0.0 (2)	C15—C16—C17—C12	−0.3 (3)
C3—C4—C5—C6	179.58 (15)	C13—C12—C17—C16	0.2 (3)
C10—C5—C6—C7	−1.5 (2)	C2B—C12—C17—C16	−177.9 (2)
C4—C5—C6—C7	176.75 (15)	C2A—C12—C17—C16	−177.50 (17)
C5—C6—C7—C8	−0.7 (2)	C10—O1—C2A—C3	42.9 (3)
C11—O2—C8—C9	−3.8 (2)	C10—O1—C2A—C12	163.97 (15)
C11—O2—C8—C7	175.80 (14)	C13—C12—C2A—O1	−62.3 (3)
C6—C7—C8—O2	−177.26 (14)	C17—C12—C2A—O1	114.88 (19)
C6—C7—C8—C9	2.3 (2)	C13—C12—C2A—C3	61.4 (3)
O2—C8—C9—C10	177.95 (13)	C17—C12—C2A—C3	−121.4 (2)
C7—C8—C9—C10	−1.6 (2)	C10—O1—C2B—C3	−44.2 (3)
C2A—O1—C10—C5	−24.6 (2)	C10—O1—C2B—C12	−167.06 (16)
C2B—O1—C10—C5	18.7 (2)	C13—C12—C2B—C3	121.6 (2)
C2A—O1—C10—C9	155.59 (18)	C17—C12—C2B—C3	−60.0 (4)
C2B—O1—C10—C9	−161.12 (19)	C13—C12—C2B—O1	−113.9 (2)
C6—C5—C10—O1	−177.56 (13)	C17—C12—C2B—O1	64.5 (3)
C4—C5—C10—O1	4.2 (2)	O1—C2B—C3—C4	45.8 (3)
C6—C5—C10—C9	2.3 (2)	C12—C2B—C3—C4	162.6 (2)
C4—C5—C10—C9	−176.02 (13)	O1—C2A—C3—C4	−41.0 (3)
C8—C9—C10—O1	179.09 (12)	C12—C2A—C3—C4	−157.19 (18)
C8—C9—C10—C5	−0.7 (2)	O4—C4—C3—C2B	157.1 (2)
C17—C12—C13—C14	−0.1 (3)	C5—C4—C3—C2B	−22.5 (3)
C2B—C12—C13—C14	178.76 (19)	O4—C4—C3—C2A	−159.74 (19)
C2A—C12—C13—C14	176.8 (2)	C5—C4—C3—C2A	20.7 (3)
C12—C13—C14—C15	0.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O4^i	0.95	2.64	3.439 (3)	158

Symmetry code: (i) x+1, y−1, z.

2-(4-Methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one (FL2)

Crystal data

C16H14O3	Dx = 1.338 Mg m^−3
Mr = 254.27	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 10611 reflections
a = 12.7692 (2) Å	θ = 3.4–35.7°
b = 8.5258 (1) Å	µ = 0.09 mm^−1
c = 23.1820 (3) Å	T = 100 K
V = 2523.77 (6) Å^3	Prism, colourless
Z = 8	0.4 × 0.2 × 0.1 mm
F(000) = 1072

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas detector	2615 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	2267 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.027
Detector resolution: 10.4498 pixels mm^-1	θmax = 26.5°, θmin = 3.0°
ω scans	h = −16→16
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −9→10
Tmin = 0.671, Tmax = 1.000	l = −28→29
19929 measured reflections

Refinement

Refinement on F^2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.144	w = 1/[σ^2(Fo^2) + (0.0575P)^2 + 2.4485P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2615 reflections	Δρmax = 0.46 e Å^−3
183 parameters	Δρmin = −0.53 e Å^−3
3 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.

Refinement. Single-crystal X-ray data of five flavanone derivatives (FL1, FL2, FL3, FL5 and FL8) were collected on a micro-focus SuperNova diffractometer with an Atlas detector, whereas data collection of two chalcone derivatives (CH2 and CH4) was carried out on an Xcalibur diffractometer with a Sapphire3 detector; all using Mo Kα and ω scans at a low temperature of 100.0 (1) K. The X-ray data were corrected for absorption using CrysAlis PRO (Agilent, 2015). All structures were solved using SHELXT (Sheldrick, 2015a) and refined with SHELXL2014/7 (Sheldrick, 2015b). All non-H atoms were refined anisotropically.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.37524 (9)	0.14801 (14)	0.58084 (5)	0.0276 (3)
O2	0.85340 (10)	0.11366 (18)	0.64971 (6)	0.0374 (4)
O4	0.18991 (11)	−0.08707 (19)	0.69662 (6)	0.0439 (4)
C4	0.24514 (15)	−0.0228 (2)	0.66092 (8)	0.0326 (4)
C5	0.20276 (14)	0.0562 (2)	0.60943 (8)	0.0274 (4)
C6	0.09534 (15)	0.0504 (2)	0.59704 (9)	0.0343 (4)
H6	0.0496	−0.0060	0.6218	0.041*
C7	0.05564 (16)	0.1258 (2)	0.54939 (10)	0.0396 (5)
H7	−0.0172	0.1214	0.5412	0.048*
C8	0.12270 (16)	0.2083 (3)	0.51319 (9)	0.0413 (5)
H8	0.0951	0.2600	0.4802	0.050*
C9	0.22914 (15)	0.2163 (2)	0.52445 (8)	0.0345 (4)
H9	0.2741	0.2741	0.4997	0.041*
C10	0.26957 (13)	0.13885 (19)	0.57245 (7)	0.0259 (4)
C12	0.53084 (16)	0.0909 (4)	0.63301 (11)	0.0615 (8)
C13	0.59748 (17)	0.0045 (3)	0.59844 (10)	0.0486 (6)
H13	0.5689	−0.0635	0.5700	0.058*
C14	0.70479 (15)	0.0150 (2)	0.60446 (8)	0.0336 (4)
H14	0.7496	−0.0441	0.5800	0.040*
C15	0.74675 (14)	0.1122 (2)	0.64637 (7)	0.0280 (4)
C16	0.68152 (17)	0.2008 (2)	0.68107 (9)	0.0408 (5)
H16	0.7101	0.2684	0.7096	0.049*
C17	0.57444 (19)	0.1900 (3)	0.67388 (11)	0.0566 (7)
H17	0.5297	0.2518	0.6974	0.068*
C18	0.89804 (19)	0.1915 (3)	0.69807 (9)	0.0567 (7)
H18A	0.8797	0.3031	0.6968	0.085*
H18B	0.9744	0.1801	0.6970	0.085*
H18C	0.8708	0.1450	0.7337	0.085*
C2A	0.4103 (2)	0.1137 (3)	0.63910 (13)	0.0241 (10)	0.526 (7)
H2A	0.3978	0.2089	0.6633	0.029*	0.526 (7)
C2B	0.4192 (2)	0.0302 (4)	0.61717 (12)	0.0279 (12)	0.474 (7)
H2B	0.4287	−0.0657	0.5929	0.033*	0.474 (7)
C3	0.36129 (17)	−0.0153 (4)	0.66630 (10)	0.0617 (8)
H3A	0.3793	−0.0128	0.7078	0.074*	0.526 (7)
H3B	0.3911	−0.1129	0.6500	0.074*	0.526 (7)
H3C	0.3782	0.0587	0.6979	0.074*	0.474 (7)
H3D	0.3864	−0.1201	0.6784	0.074*	0.474 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0277 (6)	0.0314 (7)	0.0236 (6)	−0.0022 (5)	−0.0015 (5)	0.0043 (5)
O2	0.0269 (7)	0.0527 (9)	0.0326 (7)	−0.0106 (6)	−0.0012 (5)	−0.0044 (6)
O4	0.0405 (8)	0.0533 (9)	0.0380 (8)	−0.0070 (7)	0.0092 (6)	0.0104 (7)
C4	0.0343 (9)	0.0334 (9)	0.0302 (9)	−0.0041 (8)	0.0032 (8)	0.0018 (7)
C5	0.0293 (9)	0.0217 (8)	0.0313 (9)	0.0019 (7)	0.0015 (7)	−0.0040 (7)
C6	0.0298 (9)	0.0261 (9)	0.0471 (11)	0.0002 (7)	0.0023 (8)	−0.0019 (8)
C7	0.0316 (10)	0.0338 (10)	0.0535 (12)	0.0011 (8)	−0.0088 (9)	−0.0055 (9)
C8	0.0424 (11)	0.0425 (11)	0.0391 (11)	0.0023 (9)	−0.0139 (9)	0.0026 (9)
C9	0.0389 (11)	0.0371 (10)	0.0275 (9)	−0.0018 (8)	−0.0049 (8)	0.0011 (7)
C10	0.0281 (9)	0.0235 (8)	0.0261 (8)	0.0008 (7)	−0.0020 (7)	−0.0047 (6)
C12	0.0247 (10)	0.102 (2)	0.0580 (14)	0.0043 (12)	0.0037 (10)	0.0554 (15)
C13	0.0384 (11)	0.0640 (14)	0.0433 (11)	−0.0222 (11)	−0.0151 (9)	0.0192 (11)
C14	0.0330 (9)	0.0365 (10)	0.0315 (9)	−0.0034 (8)	−0.0016 (7)	−0.0010 (8)
C15	0.0264 (8)	0.0302 (9)	0.0274 (8)	−0.0046 (7)	0.0028 (7)	0.0024 (7)
C16	0.0534 (12)	0.0334 (10)	0.0356 (10)	0.0005 (9)	0.0156 (9)	0.0020 (8)
C17	0.0473 (13)	0.0677 (16)	0.0549 (14)	0.0277 (12)	0.0276 (11)	0.0330 (13)
C18	0.0546 (14)	0.0864 (19)	0.0291 (10)	−0.0389 (13)	−0.0094 (9)	0.0048 (11)
C2A	0.0302 (18)	0.0223 (18)	0.0198 (16)	0.0054 (13)	0.0008 (12)	−0.0027 (13)
C2B	0.0276 (19)	0.027 (2)	0.029 (2)	0.0065 (15)	0.0015 (15)	0.0038 (17)
C3	0.0374 (12)	0.097 (2)	0.0504 (13)	−0.0251 (13)	−0.0147 (10)	0.0452 (14)

Geometric parameters (Å, º)

O1—C10	1.365 (2)	C12—C2B	1.561 (3)
O1—C2B	1.426 (3)	C13—C14	1.380 (3)
O1—C2A	1.453 (3)	C13—H13	0.9500
O2—C15	1.364 (2)	C14—C15	1.385 (3)
O2—C18	1.422 (2)	C14—H14	0.9500
O4—C4	1.218 (2)	C15—C16	1.382 (3)
C4—C5	1.474 (2)	C16—C17	1.381 (3)
C4—C3	1.490 (3)	C16—H16	0.9500
C5—C10	1.400 (2)	C17—H17	0.9500
C5—C6	1.402 (3)	C18—H18A	0.9800
C6—C7	1.375 (3)	C18—H18B	0.9800
C6—H6	0.9500	C18—H18C	0.9800
C7—C8	1.390 (3)	C2A—C3	1.414 (3)
C7—H7	0.9500	C2A—H2A	1.0000
C8—C9	1.386 (3)	C2B—C3	1.412 (3)
C8—H8	0.9500	C2B—H2B	1.0000
C9—C10	1.393 (2)	C3—H3A	0.9900
C9—H9	0.9500	C3—H3B	0.9900
C12—C13	1.382 (4)	C3—H3C	0.9900
C12—C17	1.386 (4)	C3—H3D	0.9900
C12—C2A	1.558 (3)
C10—O1—C2B	115.64 (15)	C16—C15—C14	120.13 (19)
C10—O1—C2A	115.19 (15)	C17—C16—C15	119.4 (2)
C15—O2—C18	116.69 (16)	C17—C16—H16	120.3
O4—C4—C5	122.93 (18)	C15—C16—H16	120.3
O4—C4—C3	122.62 (18)	C16—C17—C12	121.4 (2)
C5—C4—C3	114.43 (16)	C16—C17—H17	119.3
C10—C5—C6	119.24 (16)	C12—C17—H17	119.3
C10—C5—C4	120.16 (16)	O2—C18—H18A	109.5
C6—C5—C4	120.59 (17)	O2—C18—H18B	109.5
C7—C6—C5	120.59 (18)	H18A—C18—H18B	109.5
C7—C6—H6	119.7	O2—C18—H18C	109.5
C5—C6—H6	119.7	H18A—C18—H18C	109.5
C6—C7—C8	119.63 (18)	H18B—C18—H18C	109.5
C6—C7—H7	120.2	C3—C2A—O1	115.8 (2)
C8—C7—H7	120.2	C3—C2A—C12	112.37 (19)
C9—C8—C7	121.03 (18)	O1—C2A—C12	104.21 (18)
C9—C8—H8	119.5	C3—C2A—H2A	108.1
C7—C8—H8	119.5	O1—C2A—H2A	108.1
C8—C9—C10	119.37 (18)	C12—C2A—H2A	108.1
C8—C9—H9	120.3	C3—C2B—O1	117.6 (2)
C10—C9—H9	120.3	C3—C2B—C12	112.29 (19)
O1—C10—C9	116.92 (15)	O1—C2B—C12	105.4 (2)
O1—C10—C5	122.95 (15)	C3—C2B—H2B	107.0
C9—C10—C5	120.13 (16)	O1—C2B—H2B	107.0
C13—C12—C17	118.3 (2)	C12—C2B—H2B	107.0
C13—C12—C2A	136.7 (3)	C2B—C3—C4	117.73 (19)
C17—C12—C2A	105.0 (2)	C2A—C3—C4	115.9 (2)
C13—C12—C2B	104.4 (2)	C2A—C3—H3A	108.3
C17—C12—C2B	136.9 (2)	C4—C3—H3A	108.3
C12—C13—C14	121.2 (2)	C2A—C3—H3B	108.3
C12—C13—H13	119.4	C4—C3—H3B	108.3
C14—C13—H13	119.4	H3A—C3—H3B	107.4
C13—C14—C15	119.6 (2)	C2B—C3—H3C	107.9
C13—C14—H14	120.2	C4—C3—H3C	107.9
C15—C14—H14	120.2	C2B—C3—H3D	107.9
O2—C15—C16	124.30 (17)	C4—C3—H3D	107.9
O2—C15—C14	115.56 (16)	H3C—C3—H3D	107.2
O4—C4—C5—C10	174.82 (18)	O2—C15—C16—C17	180.00 (18)
C3—C4—C5—C10	−4.2 (3)	C14—C15—C16—C17	0.7 (3)
O4—C4—C5—C6	−4.8 (3)	C15—C16—C17—C12	0.7 (3)
C3—C4—C5—C6	176.2 (2)	C13—C12—C17—C16	−1.3 (3)
C10—C5—C6—C7	−0.4 (3)	C2A—C12—C17—C16	179.9 (2)
C4—C5—C6—C7	179.21 (17)	C2B—C12—C17—C16	170.3 (3)
C5—C6—C7—C8	0.0 (3)	C10—O1—C2A—C3	42.2 (3)
C6—C7—C8—C9	−0.2 (3)	C10—O1—C2A—C12	166.16 (18)
C7—C8—C9—C10	0.7 (3)	C13—C12—C2A—C3	75.4 (4)
C2B—O1—C10—C9	−160.1 (2)	C17—C12—C2A—C3	−106.2 (2)
C2A—O1—C10—C9	160.29 (18)	C13—C12—C2A—O1	−50.7 (3)
C2B—O1—C10—C5	19.8 (3)	C17—C12—C2A—O1	127.7 (2)
C2A—O1—C10—C5	−19.9 (2)	C10—O1—C2B—C3	−39.2 (3)
C8—C9—C10—O1	178.71 (17)	C10—O1—C2B—C12	−165.24 (17)
C8—C9—C10—C5	−1.2 (3)	C13—C12—C2B—C3	127.8 (3)
C6—C5—C10—O1	−178.86 (15)	C17—C12—C2B—C3	−44.6 (4)
C4—C5—C10—O1	1.5 (2)	C13—C12—C2B—O1	−102.9 (2)
C6—C5—C10—C9	1.0 (3)	C17—C12—C2B—O1	84.7 (3)
C4—C5—C10—C9	−178.64 (16)	O1—C2B—C3—C4	36.9 (4)
C17—C12—C13—C14	0.5 (3)	C12—C2B—C3—C4	159.5 (3)
C2A—C12—C13—C14	178.8 (2)	O1—C2A—C3—C4	−45.7 (3)
C2B—C12—C13—C14	−173.6 (2)	C12—C2A—C3—C4	−165.2 (2)
C12—C13—C14—C15	0.9 (3)	O4—C4—C3—C2B	166.2 (2)
C18—O2—C15—C16	10.7 (3)	C5—C4—C3—C2B	−14.8 (3)
C18—O2—C15—C14	−169.96 (18)	O4—C4—C3—C2A	−152.8 (2)
C13—C14—C15—O2	179.15 (17)	C5—C4—C3—C2A	26.1 (3)
C13—C14—C15—C16	−1.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O4^i	0.95	2.51	3.365 (3)	149
C2A—H2A···O4^ii	1.00	2.21	3.150 (3)	156

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

2-(4-Methoxyphenyl)-6-methyl-3,4-dihydro-2H-1-benzopyran-4-one (FL3)

Crystal data

C17H16O3	F(000) = 1136
Mr = 268.30	Dx = 1.320 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 16.7561 (3) Å	Cell parameters from 12573 reflections
b = 8.0448 (1) Å	θ = 3.6–39.6°
c = 21.3319 (4) Å	µ = 0.09 mm^−1
β = 110.138 (2)°	T = 100 K
V = 2699.74 (8) Å^3	Prism, colourless
Z = 8	0.3 × 0.2 × 0.1 mm

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas detector	5586 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	4898 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.024
Detector resolution: 10.4498 pixels mm^-1	θmax = 26.5°, θmin = 2.9°
ω scans	h = −21→17
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −10→9
Tmin = 0.752, Tmax = 1.000	l = −26→26
21035 measured reflections

Refinement

Refinement on F^2	Primary atom site location: difference Fourier map
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) = 0.108	w = 1/[σ^2(Fo^2) + (0.0398P)^2 + 1.780P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
5586 reflections	Δρmax = 0.40 e Å^−3
391 parameters	Δρmin = −0.32 e Å^−3
5 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.

Refinement. Single-crystal X-ray data of five flavanone derivatives (FL1, FL2, FL3, FL5 and FL8) were collected on a micro-focus SuperNova diffractometer with an Atlas detector, whereas data collection of two chalcone derivatives (CH2 and CH4) was carried out on an Xcalibur diffractometer with a Sapphire3 detector; all using Mo Kα and ω scans at a low temperature of 100.0 (1) K. The X-ray data were corrected for absorption using CrysAlis PRO (Agilent, 2015). All structures were solved using SHELXT (Sheldrick, 2015a) and refined with SHELXL2014/7 (Sheldrick, 2015b). All non-H atoms were refined anisotropically.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.93501 (6)	0.43575 (12)	0.37957 (5)	0.0233 (2)
O2	0.54766 (7)	0.58037 (14)	0.23161 (6)	0.0329 (3)
O4	1.08460 (8)	0.85266 (14)	0.42977 (7)	0.0426 (3)
C2A	0.90139 (17)	0.5977 (3)	0.3841 (2)	0.0166 (8)	0.549 (7)
H2A	0.9024	0.6171	0.4307	0.020*	0.549 (7)
C3A	0.94944 (15)	0.7382 (3)	0.36373 (18)	0.0210 (8)	0.549 (7)
H3A	0.9235	0.8474	0.3662	0.025*	0.549 (7)
H3B	0.9492	0.7212	0.3177	0.025*	0.549 (7)
C2B	0.9028 (2)	0.5952 (4)	0.3525 (3)	0.0273 (11)	0.451 (7)
H2B	0.9154	0.6125	0.3104	0.033*	0.451 (7)
C3B	0.94369 (14)	0.7304 (4)	0.4000 (3)	0.0300 (13)	0.451 (7)
H3C	0.9319	0.7151	0.4420	0.036*	0.451 (7)
H3D	0.9200	0.8391	0.3806	0.036*	0.451 (7)
C4	1.04103 (10)	0.7280 (2)	0.41481 (9)	0.0363 (4)
C5	1.07587 (9)	0.55827 (17)	0.42790 (7)	0.0203 (3)
C6	1.16360 (9)	0.53184 (18)	0.45720 (7)	0.0207 (3)
H6	1.2004	0.6250	0.4707	0.025*
C7	1.19798 (9)	0.37352 (18)	0.46702 (7)	0.0201 (3)
C8	1.14183 (9)	0.23843 (18)	0.44596 (7)	0.0207 (3)
H8	1.1643	0.1288	0.4514	0.025*
C9	1.05490 (9)	0.26039 (17)	0.41753 (7)	0.0211 (3)
H9	1.0183	0.1669	0.4042	0.025*
C10	1.02144 (9)	0.42092 (17)	0.40862 (7)	0.0192 (3)
C11	1.29227 (9)	0.3442 (2)	0.49896 (7)	0.0250 (3)
H11A	1.3220	0.4512	0.5075	0.037*
H11B	1.3124	0.2777	0.4689	0.037*
H11C	1.3036	0.2845	0.5412	0.037*
C12	0.80738 (9)	0.59108 (18)	0.33540 (9)	0.0308 (4)
C13	0.75563 (10)	0.49805 (18)	0.36045 (7)	0.0247 (3)
H13	0.7804	0.4378	0.4008	0.030*
C14	0.66838 (9)	0.49090 (17)	0.32784 (7)	0.0213 (3)
H14	0.6337	0.4268	0.3458	0.026*
C15	0.63221 (9)	0.57846 (17)	0.26866 (7)	0.0196 (3)
C16	0.68325 (9)	0.67314 (18)	0.24306 (7)	0.0225 (3)
H16	0.6585	0.7337	0.2028	0.027*
C17	0.76978 (10)	0.67892 (19)	0.27625 (9)	0.0289 (3)
H17	0.8044	0.7439	0.2585	0.035*
C18	0.49235 (11)	0.4864 (3)	0.25648 (13)	0.0547 (6)
H18A	0.5107	0.3700	0.2620	0.082*
H18B	0.4340	0.4932	0.2248	0.082*
H18C	0.4945	0.5317	0.2997	0.082*
O51	0.36187 (6)	0.17192 (12)	0.21123 (5)	0.0216 (2)
O52	0.71873 (7)	0.11084 (14)	0.43352 (5)	0.0276 (2)
O54	0.21703 (7)	−0.24907 (13)	0.16086 (5)	0.0263 (2)
C52A	0.37855 (10)	0.03419 (19)	0.25971 (8)	0.0202 (4)	0.932 (3)
H52A	0.3425	0.0514	0.2880	0.024*	0.932 (3)
C53A	0.35236 (10)	−0.12833 (19)	0.22231 (8)	0.0213 (4)	0.932 (3)
H53A	0.3624	−0.2212	0.2545	0.026*	0.932 (3)
H53B	0.3871	−0.1479	0.1937	0.026*	0.932 (3)
C52B	0.4030 (11)	0.0116 (9)	0.2363 (6)	0.0202 (4)	0.068 (3)
H52B	0.4274	−0.0415	0.2045	0.024*	0.068 (3)
C53B	0.3300 (12)	−0.092 (3)	0.2452 (7)	0.0213 (4)	0.068 (3)
H53C	0.3528	−0.2003	0.2657	0.026*	0.068 (3)
H53D	0.3069	−0.0331	0.2759	0.026*	0.068 (3)
C54	0.25884 (9)	−0.12241 (18)	0.17932 (7)	0.0217 (3)
C55	0.22381 (9)	0.04487 (18)	0.15735 (7)	0.0202 (3)
C56	0.13815 (9)	0.06681 (18)	0.11817 (7)	0.0217 (3)
H56	0.1010	−0.0262	0.1095	0.026*
C57	0.10606 (9)	0.22006 (19)	0.09179 (7)	0.0227 (3)
C58	0.16332 (9)	0.35324 (19)	0.10363 (7)	0.0243 (3)
H58	0.1433	0.4582	0.0842	0.029*
C59	0.24797 (9)	0.33659 (18)	0.14273 (7)	0.0239 (3)
H59	0.2852	0.4293	0.1502	0.029*
C60	0.27838 (9)	0.18274 (18)	0.17123 (7)	0.0200 (3)
C61	0.01240 (9)	0.2432 (2)	0.05307 (8)	0.0282 (3)
H61A	−0.0116	0.1387	0.0310	0.042*
H61B	0.0050	0.3303	0.0194	0.042*
H61C	−0.0170	0.2758	0.0837	0.042*
C62	0.47052 (9)	0.04642 (18)	0.30397 (8)	0.0243 (3)
C63	0.53657 (10)	−0.0287 (2)	0.28915 (8)	0.0285 (3)
H63	0.5241	−0.0934	0.2497	0.034*
C64	0.62090 (9)	−0.01086 (19)	0.33126 (8)	0.0264 (3)
H64	0.6655	−0.0629	0.3206	0.032*
C65	0.63882 (9)	0.08347 (18)	0.38873 (7)	0.0217 (3)
C66	0.57303 (10)	0.15820 (19)	0.40451 (8)	0.0255 (3)
H66	0.5853	0.2218	0.4442	0.031*
C67	0.49030 (10)	0.13952 (18)	0.36242 (8)	0.0261 (3)
H67	0.4458	0.1911	0.3734	0.031*
C68	0.78807 (9)	0.0417 (2)	0.41763 (8)	0.0309 (4)
H68A	0.7827	−0.0797	0.4152	0.046*
H68B	0.8418	0.0721	0.4524	0.046*
H68C	0.7872	0.0851	0.3745	0.046*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0177 (5)	0.0144 (5)	0.0316 (6)	0.0001 (4)	0.0004 (4)	−0.0026 (4)
O2	0.0201 (5)	0.0243 (6)	0.0439 (7)	−0.0035 (4)	−0.0021 (5)	0.0079 (5)
O4	0.0319 (6)	0.0160 (6)	0.0611 (8)	−0.0044 (5)	−0.0082 (6)	−0.0031 (5)
C2A	0.0177 (13)	0.0121 (13)	0.0149 (18)	0.0006 (9)	−0.0009 (12)	0.0091 (11)
C3A	0.0230 (14)	0.0157 (13)	0.0190 (17)	0.0003 (10)	0.0006 (12)	0.0047 (12)
C2B	0.0283 (19)	0.0254 (19)	0.020 (3)	−0.0005 (14)	−0.0019 (18)	0.0150 (17)
C3B	0.0280 (19)	0.0146 (17)	0.034 (3)	0.0035 (13)	−0.0072 (16)	−0.0028 (17)
C4	0.0255 (8)	0.0173 (8)	0.0509 (11)	−0.0012 (6)	−0.0064 (7)	−0.0047 (7)
C5	0.0228 (7)	0.0153 (7)	0.0197 (7)	−0.0009 (5)	0.0034 (5)	−0.0008 (5)
C6	0.0224 (7)	0.0191 (7)	0.0184 (7)	−0.0041 (5)	0.0044 (5)	−0.0012 (5)
C7	0.0197 (7)	0.0230 (7)	0.0161 (6)	0.0000 (6)	0.0045 (5)	0.0002 (5)
C8	0.0241 (7)	0.0171 (7)	0.0189 (7)	0.0030 (5)	0.0048 (5)	0.0004 (5)
C9	0.0229 (7)	0.0152 (7)	0.0221 (7)	−0.0029 (5)	0.0039 (6)	−0.0016 (5)
C10	0.0193 (7)	0.0181 (7)	0.0178 (6)	−0.0007 (5)	0.0033 (5)	−0.0007 (5)
C11	0.0206 (7)	0.0277 (8)	0.0246 (7)	0.0016 (6)	0.0050 (6)	0.0005 (6)
C12	0.0187 (7)	0.0156 (7)	0.0503 (10)	0.0005 (6)	0.0020 (7)	0.0060 (7)
C13	0.0300 (8)	0.0160 (7)	0.0223 (7)	0.0012 (6)	0.0017 (6)	0.0017 (6)
C14	0.0267 (7)	0.0158 (7)	0.0232 (7)	0.0003 (6)	0.0109 (6)	0.0005 (5)
C15	0.0195 (7)	0.0139 (6)	0.0234 (7)	0.0008 (5)	0.0046 (5)	−0.0024 (5)
C16	0.0285 (8)	0.0165 (7)	0.0222 (7)	0.0038 (6)	0.0084 (6)	0.0033 (5)
C17	0.0262 (8)	0.0173 (7)	0.0474 (10)	0.0022 (6)	0.0179 (7)	0.0092 (7)
C18	0.0203 (8)	0.0405 (11)	0.0943 (17)	−0.0063 (8)	0.0081 (9)	0.0218 (11)
O51	0.0198 (5)	0.0169 (5)	0.0252 (5)	−0.0019 (4)	0.0038 (4)	0.0021 (4)
O52	0.0236 (5)	0.0305 (6)	0.0253 (5)	−0.0017 (4)	0.0039 (4)	−0.0016 (5)
O54	0.0287 (5)	0.0185 (5)	0.0310 (6)	−0.0066 (4)	0.0094 (4)	−0.0016 (4)
C52A	0.0223 (8)	0.0175 (7)	0.0214 (8)	0.0015 (6)	0.0084 (6)	0.0010 (6)
C53A	0.0241 (8)	0.0157 (7)	0.0229 (8)	0.0005 (6)	0.0065 (6)	0.0009 (6)
C52B	0.0223 (8)	0.0175 (7)	0.0214 (8)	0.0015 (6)	0.0084 (6)	0.0010 (6)
C53B	0.0241 (8)	0.0157 (7)	0.0229 (8)	0.0005 (6)	0.0065 (6)	0.0009 (6)
C54	0.0259 (7)	0.0195 (7)	0.0206 (7)	−0.0039 (6)	0.0092 (6)	−0.0010 (6)
C55	0.0226 (7)	0.0186 (7)	0.0207 (7)	−0.0019 (5)	0.0093 (6)	−0.0028 (5)
C56	0.0222 (7)	0.0211 (7)	0.0234 (7)	−0.0046 (6)	0.0098 (6)	−0.0059 (6)
C57	0.0209 (7)	0.0253 (7)	0.0212 (7)	0.0001 (6)	0.0067 (6)	−0.0047 (6)
C58	0.0250 (7)	0.0207 (7)	0.0255 (7)	0.0027 (6)	0.0065 (6)	0.0005 (6)
C59	0.0244 (7)	0.0183 (7)	0.0275 (7)	−0.0025 (6)	0.0068 (6)	−0.0002 (6)
C60	0.0195 (7)	0.0200 (7)	0.0201 (7)	−0.0013 (5)	0.0062 (5)	−0.0023 (5)
C61	0.0211 (7)	0.0301 (8)	0.0303 (8)	0.0008 (6)	0.0051 (6)	−0.0051 (7)
C62	0.0220 (7)	0.0173 (7)	0.0305 (8)	0.0001 (6)	0.0051 (6)	0.0054 (6)
C63	0.0282 (8)	0.0250 (8)	0.0281 (8)	0.0003 (6)	0.0044 (6)	−0.0055 (6)
C64	0.0230 (7)	0.0251 (8)	0.0300 (8)	0.0034 (6)	0.0078 (6)	−0.0038 (6)
C65	0.0216 (7)	0.0184 (7)	0.0234 (7)	−0.0011 (5)	0.0056 (6)	0.0038 (6)
C66	0.0311 (8)	0.0215 (7)	0.0261 (7)	−0.0013 (6)	0.0128 (6)	−0.0006 (6)
C67	0.0267 (8)	0.0187 (7)	0.0359 (8)	0.0022 (6)	0.0145 (6)	0.0027 (6)
C68	0.0199 (7)	0.0384 (9)	0.0311 (8)	0.0007 (6)	0.0045 (6)	0.0058 (7)

Geometric parameters (Å, º)

O1—C10	1.3702 (16)	O51—C60	1.3679 (16)
O1—C2B	1.434 (2)	O51—C52B	1.474 (5)
O1—C2A	1.436 (2)	O51—C52A	1.4753 (17)
O2—C15	1.3643 (17)	O52—C65	1.3687 (17)
O2—C18	1.432 (2)	O52—C68	1.4302 (19)
O4—C4	1.2166 (19)	O54—C54	1.2224 (17)
C2A—C3A	1.535 (5)	C52A—C62	1.508 (2)
C2A—C12	1.561 (3)	C52A—C53A	1.516 (2)
C2A—H2A	1.0000	C52A—H52A	1.0000
C3A—C4	1.548 (2)	C53A—C54	1.520 (2)
C3A—H3A	0.9900	C53A—H53A	0.9900
C3A—H3B	0.9900	C53A—H53B	0.9900
C2B—C3B	1.484 (8)	C52B—C62	1.522 (5)
C2B—C12	1.513 (4)	C52B—C53B	1.55 (3)
C2B—H2B	1.0000	C52B—H52B	1.0000
C3B—C4	1.551 (2)	C53B—C54	1.517 (5)
C3B—H3C	0.9900	C53B—H53C	0.9900
C3B—H3D	0.9900	C53B—H53D	0.9900
C4—C5	1.473 (2)	C54—C55	1.479 (2)
C5—C10	1.4012 (19)	C55—C56	1.401 (2)
C5—C6	1.4015 (19)	C55—C60	1.4026 (19)
C6—C7	1.384 (2)	C56—C57	1.385 (2)
C6—H6	0.9500	C56—H56	0.9500
C7—C8	1.406 (2)	C57—C58	1.402 (2)
C7—C11	1.5082 (19)	C57—C61	1.5125 (19)
C8—C9	1.3829 (19)	C58—C59	1.382 (2)
C8—H8	0.9500	C58—H58	0.9500
C9—C10	1.3945 (19)	C59—C60	1.396 (2)
C9—H9	0.9500	C59—H59	0.9500
C11—H11A	0.9800	C61—H61A	0.9800
C11—H11B	0.9800	C61—H61B	0.9800
C11—H11C	0.9800	C61—H61C	0.9800
C12—C13	1.384 (2)	C62—C63	1.390 (2)
C12—C17	1.393 (2)	C62—C67	1.393 (2)
C13—C14	1.387 (2)	C63—C64	1.397 (2)
C13—H13	0.9500	C63—H63	0.9500
C14—C15	1.389 (2)	C64—C65	1.384 (2)
C14—H14	0.9500	C64—H64	0.9500
C15—C16	1.390 (2)	C65—C66	1.395 (2)
C16—C17	1.378 (2)	C66—C67	1.376 (2)
C16—H16	0.9500	C66—H66	0.9500
C17—H17	0.9500	C67—H67	0.9500
C18—H18A	0.9800	C68—H68A	0.9800
C18—H18B	0.9800	C68—H68B	0.9800
C18—H18C	0.9800	C68—H68C	0.9800
C10—O1—C2B	116.93 (19)	C60—O51—C52B	122.2 (6)
C10—O1—C2A	115.25 (15)	C60—O51—C52A	113.03 (10)
C15—O2—C18	117.06 (13)	C65—O52—C68	116.83 (12)
O1—C2A—C3A	113.1 (3)	O51—C52A—C62	107.21 (11)
O1—C2A—C12	104.68 (18)	O51—C52A—C53A	109.16 (12)
C3A—C2A—C12	110.1 (3)	C62—C52A—C53A	115.72 (13)
O1—C2A—H2A	109.6	O51—C52A—H52A	108.2
C3A—C2A—H2A	109.6	C62—C52A—H52A	108.2
C12—C2A—H2A	109.6	C53A—C52A—H52A	108.2
C2A—C3A—C4	104.6 (2)	C52A—C53A—C54	110.00 (13)
C2A—C3A—H3A	110.8	C52A—C53A—H53A	109.7
C4—C3A—H3A	110.8	C54—C53A—H53A	109.7
C2A—C3A—H3B	110.8	C52A—C53A—H53B	109.7
C4—C3A—H3B	110.8	C54—C53A—H53B	109.7
H3A—C3A—H3B	108.9	H53A—C53A—H53B	108.2
O1—C2B—C3B	111.1 (4)	O51—C52B—C62	106.6 (4)
O1—C2B—C12	107.3 (2)	O51—C52B—C53B	103.0 (15)
C3B—C2B—C12	112.4 (4)	C62—C52B—C53B	110.1 (13)
O1—C2B—H2B	108.6	O51—C52B—H52B	112.2
C3B—C2B—H2B	108.6	C62—C52B—H52B	112.2
C12—C2B—H2B	108.6	C53B—C52B—H52B	112.2
C2B—C3B—C4	109.6 (3)	C54—C53B—C52B	112.1 (13)
C2B—C3B—H3C	109.7	C54—C53B—H53C	109.2
C4—C3B—H3C	109.7	C52B—C53B—H53C	109.2
C2B—C3B—H3D	109.7	C54—C53B—H53D	109.2
C4—C3B—H3D	109.7	C52B—C53B—H53D	109.2
H3C—C3B—H3D	108.2	H53C—C53B—H53D	107.9
O4—C4—C5	123.46 (14)	O54—C54—C55	122.38 (13)
O4—C4—C3A	120.06 (17)	O54—C54—C53B	127.8 (8)
C5—C4—C3A	114.48 (15)	C55—C54—C53B	104.3 (9)
O4—C4—C3B	122.49 (19)	O54—C54—C53A	121.73 (13)
C5—C4—C3B	111.74 (18)	C55—C54—C53A	115.73 (12)
C10—C5—C6	119.21 (13)	C56—C55—C60	119.06 (13)
C10—C5—C4	119.99 (13)	C56—C55—C54	121.13 (13)
C6—C5—C4	120.76 (13)	C60—C55—C54	119.61 (12)
C7—C6—C5	121.68 (13)	C57—C56—C55	121.95 (13)
C7—C6—H6	119.2	C57—C56—H56	119.0
C5—C6—H6	119.2	C55—C56—H56	119.0
C6—C7—C8	117.72 (12)	C56—C57—C58	117.47 (13)
C6—C7—C11	121.96 (13)	C56—C57—C61	121.09 (13)
C8—C7—C11	120.32 (13)	C58—C57—C61	121.42 (14)
C9—C8—C7	121.96 (13)	C59—C58—C57	122.08 (14)
C9—C8—H8	119.0	C59—C58—H58	119.0
C7—C8—H8	119.0	C57—C58—H58	119.0
C8—C9—C10	119.43 (13)	C58—C59—C60	119.58 (13)
C8—C9—H9	120.3	C58—C59—H59	120.2
C10—C9—H9	120.3	C60—C59—H59	120.2
O1—C10—C9	117.06 (12)	O51—C60—C59	118.02 (12)
O1—C10—C5	122.94 (12)	O51—C60—C55	122.26 (13)
C9—C10—C5	119.99 (13)	C59—C60—C55	119.71 (13)
C7—C11—H11A	109.5	C57—C61—H61A	109.5
C7—C11—H11B	109.5	C57—C61—H61B	109.5
H11A—C11—H11B	109.5	H61A—C61—H61B	109.5
C7—C11—H11C	109.5	C57—C61—H61C	109.5
H11A—C11—H11C	109.5	H61A—C61—H61C	109.5
H11B—C11—H11C	109.5	H61B—C61—H61C	109.5
C13—C12—C17	118.41 (14)	C63—C62—C67	118.35 (14)
C13—C12—C2B	132.0 (2)	C63—C62—C52A	123.46 (14)
C17—C12—C2B	108.5 (2)	C67—C62—C52A	118.19 (14)
C13—C12—C2A	112.6 (2)	C63—C62—C52B	95.4 (8)
C17—C12—C2A	128.6 (2)	C67—C62—C52B	144.9 (6)
C12—C13—C14	121.40 (14)	C62—C63—C64	121.16 (14)
C12—C13—H13	119.3	C62—C63—H63	119.4
C14—C13—H13	119.3	C64—C63—H63	119.4
C13—C14—C15	119.30 (13)	C65—C64—C63	119.29 (14)
C13—C14—H14	120.4	C65—C64—H64	120.4
C15—C14—H14	120.4	C63—C64—H64	120.4
O2—C15—C14	124.98 (13)	O52—C65—C64	124.63 (13)
O2—C15—C16	115.02 (13)	O52—C65—C66	115.27 (13)
C14—C15—C16	120.00 (13)	C64—C65—C66	120.10 (13)
C17—C16—C15	119.83 (13)	C67—C66—C65	119.86 (14)
C17—C16—H16	120.1	C67—C66—H66	120.1
C15—C16—H16	120.1	C65—C66—H66	120.1
C16—C17—C12	121.06 (14)	C66—C67—C62	121.23 (14)
C16—C17—H17	119.5	C66—C67—H67	119.4
C12—C17—H17	119.5	C62—C67—H67	119.4
O2—C18—H18A	109.5	O52—C68—H68A	109.5
O2—C18—H18B	109.5	O52—C68—H68B	109.5
H18A—C18—H18B	109.5	H68A—C68—H68B	109.5
O2—C18—H18C	109.5	O52—C68—H68C	109.5
H18A—C18—H18C	109.5	H68A—C68—H68C	109.5
H18B—C18—H18C	109.5	H68B—C68—H68C	109.5
C10—O1—C2A—C3A	48.5 (4)	C60—O51—C52A—C62	−175.14 (12)
C10—O1—C2A—C12	168.42 (17)	C60—O51—C52A—C53A	58.80 (16)
O1—C2A—C3A—C4	−62.1 (4)	O51—C52A—C53A—C54	−58.34 (17)
C12—C2A—C3A—C4	−178.89 (19)	C62—C52A—C53A—C54	−179.35 (13)
C10—O1—C2B—C3B	−46.2 (6)	C60—O51—C52B—C62	−148.9 (8)
C10—O1—C2B—C12	−169.5 (3)	C60—O51—C52B—C53B	−32.9 (14)
O1—C2B—C3B—C4	60.1 (6)	O51—C52B—C53B—C54	63.6 (18)
C12—C2B—C3B—C4	−179.6 (2)	C62—C52B—C53B—C54	177.0 (12)
C2A—C3A—C4—O4	−151.0 (3)	C52B—C53B—C54—O54	141.1 (10)
C2A—C3A—C4—C5	44.6 (3)	C52B—C53B—C54—C55	−65.1 (17)
C2B—C3B—C4—O4	151.4 (3)	C52A—C53A—C54—O54	−157.54 (14)
C2B—C3B—C4—C5	−45.3 (5)	C52A—C53A—C54—C55	26.82 (19)
O4—C4—C5—C10	−179.48 (18)	O54—C54—C55—C56	5.2 (2)
C3A—C4—C5—C10	−15.6 (3)	C53B—C54—C55—C56	−150.5 (11)
C3B—C4—C5—C10	17.4 (3)	C53A—C54—C55—C56	−179.22 (14)
O4—C4—C5—C6	−2.0 (3)	O54—C54—C55—C60	−169.63 (14)
C3A—C4—C5—C6	161.8 (2)	C53B—C54—C55—C60	34.8 (11)
C3B—C4—C5—C6	−165.1 (3)	C53A—C54—C55—C60	6.0 (2)
C10—C5—C6—C7	0.6 (2)	C60—C55—C56—C57	1.1 (2)
C4—C5—C6—C7	−176.88 (15)	C54—C55—C56—C57	−173.69 (13)
C5—C6—C7—C8	0.6 (2)	C55—C56—C57—C58	2.3 (2)
C5—C6—C7—C11	−179.56 (13)	C55—C56—C57—C61	−176.36 (13)
C6—C7—C8—C9	−1.3 (2)	C56—C57—C58—C59	−3.1 (2)
C11—C7—C8—C9	178.87 (13)	C61—C57—C58—C59	175.51 (14)
C7—C8—C9—C10	0.7 (2)	C57—C58—C59—C60	0.5 (2)
C2B—O1—C10—C9	−162.0 (3)	C52B—O51—C60—C59	−171.6 (10)
C2A—O1—C10—C9	167.3 (2)	C52A—O51—C60—C59	155.67 (13)
C2B—O1—C10—C5	16.7 (4)	C52B—O51—C60—C55	7.2 (11)
C2A—O1—C10—C5	−14.0 (3)	C52A—O51—C60—C55	−25.51 (18)
C8—C9—C10—O1	179.31 (12)	C58—C59—C60—O51	−178.12 (13)
C8—C9—C10—C5	0.5 (2)	C58—C59—C60—C55	3.0 (2)
C6—C5—C10—O1	−179.89 (13)	C56—C55—C60—O51	177.38 (13)
C4—C5—C10—O1	−2.4 (2)	C54—C55—C60—O51	−7.7 (2)
C6—C5—C10—C9	−1.2 (2)	C56—C55—C60—C59	−3.8 (2)
C4—C5—C10—C9	176.34 (15)	C54—C55—C60—C59	171.09 (13)
O1—C2B—C12—C13	25.7 (6)	O51—C52A—C62—C63	−88.39 (17)
C3B—C2B—C12—C13	−96.8 (3)	C53A—C52A—C62—C63	33.7 (2)
O1—C2B—C12—C17	−142.1 (3)	O51—C52A—C62—C67	90.90 (16)
C3B—C2B—C12—C17	95.5 (5)	C53A—C52A—C62—C67	−147.06 (15)
O1—C2A—C12—C13	73.8 (3)	O51—C52B—C62—C63	−127.5 (13)
C3A—C2A—C12—C13	−164.3 (3)	C53B—C52B—C62—C63	121.4 (13)
O1—C2A—C12—C17	−113.9 (2)	O51—C52B—C62—C67	37 (2)
C3A—C2A—C12—C17	8.0 (4)	C53B—C52B—C62—C67	−74.3 (13)
C17—C12—C13—C14	0.2 (2)	C67—C62—C63—C64	−0.5 (2)
C2B—C12—C13—C14	−166.6 (4)	C52A—C62—C63—C64	178.76 (14)
C2A—C12—C13—C14	173.36 (15)	C52B—C62—C63—C64	169.3 (6)
C12—C13—C14—C15	0.3 (2)	C62—C63—C64—C65	0.0 (2)
C18—O2—C15—C14	0.9 (2)	C68—O52—C65—C64	2.6 (2)
C18—O2—C15—C16	−179.18 (16)	C68—O52—C65—C66	−177.58 (13)
C13—C14—C15—O2	179.35 (13)	C63—C64—C65—O52	−179.56 (14)
C13—C14—C15—C16	−0.6 (2)	C63—C64—C65—C66	0.6 (2)
O2—C15—C16—C17	−179.48 (13)	O52—C65—C66—C67	179.44 (13)
C14—C15—C16—C17	0.5 (2)	C64—C65—C66—C67	−0.7 (2)
C15—C16—C17—C12	0.0 (2)	C65—C66—C67—C62	0.2 (2)
C13—C12—C17—C16	−0.3 (2)	C63—C62—C67—C66	0.4 (2)
C2B—C12—C17—C16	169.3 (3)	C52A—C62—C67—C66	−178.90 (14)
C2A—C12—C17—C16	−172.25 (19)	C52B—C62—C67—C66	−161.8 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O4^i	0.95	2.55	3.231 (2)	129
C16—H16···O1^ii	0.95	2.51	3.415 (2)	160
C52A—H52A···O54^iii	1.00	2.35	3.216 (2)	145
C68—H68B···O4^iv	0.98	2.46	3.330 (2)	147

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

2-(4-Chlorophenyl)-3,4-dihydro-2H-1-benzopyran-4-one (FL5)

Crystal data

C15H11ClO2	F(000) = 536
Mr = 258.69	Dx = 1.409 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.4760 (2) Å	Cell parameters from 4722 reflections
b = 16.2902 (4) Å	θ = 3.4–33.0°
c = 11.6755 (4) Å	µ = 0.30 mm^−1
β = 97.953 (3)°	T = 100 K
V = 1219.86 (6) Å^3	Prism, colourless
Z = 4	0.3 × 0.2 × 0.1 mm

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas detector	2525 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	2414 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.015
Detector resolution: 10.4498 pixels mm^-1	θmax = 26.5°, θmin = 3.1°
ω scans	h = −5→8
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −20→20
Tmin = 0.801, Tmax = 1.000	l = −14→14
16927 measured reflections

Refinement

Refinement on F^2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.027	H-atom parameters constrained
wR(F^2) = 0.073	w = 1/[σ^2(Fo^2) + (0.0349P)^2 + 0.6483P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
2525 reflections	Δρmax = 0.32 e Å^−3
163 parameters	Δρmin = −0.26 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.

Refinement. Single-crystal X-ray data of five flavanone derivatives (FL1, FL2, FL3, FL5 and FL8) were collected on a micro-focus SuperNova diffractometer with an Atlas detector, whereas data collection of two chalcone derivatives (CH2 and CH4) was carried out on an Xcalibur diffractometer with a Sapphire3 detector; all using Mo Kα and ω scans at a low temperature of 100.0 (1) K. The X-ray data were corrected for absorption using CrysAlis PRO (Agilent, 2015). All structures were solved using SHELXT (Sheldrick, 2015a) and refined with SHELXL2014/7 (Sheldrick, 2015b). All non-H atoms were refined anisotropically.

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

	x	y	z	Uiso*/Ueq
Cl1	1.20419 (4)	0.46628 (2)	0.17410 (3)	0.01972 (10)
O1	0.54812 (12)	0.63334 (5)	0.50329 (7)	0.01536 (18)
O4	0.45832 (13)	0.88173 (5)	0.44105 (7)	0.01890 (19)
C2	0.57080 (17)	0.66607 (7)	0.38888 (9)	0.0145 (2)
H2	0.4333	0.6619	0.3383	0.017*
C3	0.63526 (18)	0.75684 (7)	0.39913 (10)	0.0166 (2)
H3A	0.7740	0.7615	0.4464	0.020*
H3B	0.6463	0.7790	0.3212	0.020*
C4	0.47772 (17)	0.80718 (7)	0.45450 (9)	0.0144 (2)
C5	0.35693 (17)	0.75952 (7)	0.53160 (9)	0.0137 (2)
C6	0.20372 (17)	0.79870 (7)	0.58686 (10)	0.0160 (2)
H6	0.1655	0.8538	0.5678	0.019*
C7	0.10829 (18)	0.75693 (7)	0.66924 (10)	0.0175 (2)
H7	0.0031	0.7830	0.7054	0.021*
C8	0.16879 (18)	0.67552 (7)	0.69884 (10)	0.0171 (2)
H8	0.1070	0.6479	0.7572	0.021*
C9	0.31722 (18)	0.63490 (7)	0.64420 (10)	0.0158 (2)
H9	0.3564	0.5801	0.6647	0.019*
C10	0.40800 (17)	0.67644 (7)	0.55821 (9)	0.0132 (2)
C12	0.72741 (18)	0.61290 (7)	0.33822 (10)	0.0146 (2)
C13	0.92054 (18)	0.59337 (7)	0.40307 (10)	0.0165 (2)
H13	0.9513	0.6115	0.4809	0.020*
C14	1.06753 (18)	0.54741 (7)	0.35354 (10)	0.0165 (2)
H14	1.1976	0.5334	0.3972	0.020*
C15	1.01883 (18)	0.52229 (7)	0.23770 (10)	0.0149 (2)
C16	0.82736 (18)	0.54032 (7)	0.17183 (10)	0.0157 (2)
H16	0.7969	0.5222	0.0940	0.019*
C17	0.68179 (17)	0.58561 (7)	0.22317 (10)	0.0152 (2)
H17	0.5504	0.5982	0.1799	0.018*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.01935 (16)	0.01612 (16)	0.02614 (17)	0.00188 (10)	0.01179 (12)	−0.00180 (11)
O1	0.0178 (4)	0.0142 (4)	0.0154 (4)	0.0032 (3)	0.0071 (3)	0.0027 (3)
O4	0.0244 (4)	0.0128 (4)	0.0206 (4)	0.0001 (3)	0.0071 (3)	0.0015 (3)
C2	0.0150 (5)	0.0154 (5)	0.0135 (5)	0.0000 (4)	0.0035 (4)	0.0014 (4)
C3	0.0182 (5)	0.0142 (5)	0.0188 (5)	0.0000 (4)	0.0076 (4)	0.0023 (4)
C4	0.0151 (5)	0.0149 (5)	0.0131 (5)	−0.0008 (4)	0.0014 (4)	−0.0005 (4)
C5	0.0143 (5)	0.0139 (5)	0.0128 (5)	−0.0016 (4)	0.0019 (4)	−0.0013 (4)
C6	0.0167 (5)	0.0139 (5)	0.0176 (5)	−0.0002 (4)	0.0027 (4)	−0.0021 (4)
C7	0.0154 (5)	0.0196 (6)	0.0186 (5)	−0.0011 (4)	0.0062 (4)	−0.0050 (4)
C8	0.0175 (5)	0.0202 (6)	0.0144 (5)	−0.0045 (4)	0.0048 (4)	−0.0004 (4)
C9	0.0175 (5)	0.0146 (5)	0.0154 (5)	−0.0014 (4)	0.0029 (4)	0.0013 (4)
C10	0.0119 (5)	0.0148 (5)	0.0127 (5)	−0.0007 (4)	0.0010 (4)	−0.0015 (4)
C12	0.0160 (5)	0.0112 (5)	0.0175 (5)	−0.0014 (4)	0.0062 (4)	0.0016 (4)
C13	0.0195 (6)	0.0167 (5)	0.0135 (5)	−0.0019 (4)	0.0035 (4)	−0.0010 (4)
C14	0.0136 (5)	0.0163 (5)	0.0194 (6)	−0.0009 (4)	0.0017 (4)	0.0024 (4)
C15	0.0163 (5)	0.0099 (5)	0.0203 (6)	−0.0009 (4)	0.0092 (4)	0.0005 (4)
C16	0.0191 (6)	0.0136 (5)	0.0149 (5)	−0.0033 (4)	0.0044 (4)	−0.0009 (4)
C17	0.0139 (5)	0.0141 (5)	0.0175 (5)	−0.0012 (4)	0.0024 (4)	0.0024 (4)

Geometric parameters (Å, º)

Cl1—C15	1.7526 (11)	C7—H7	0.9500
O1—C10	1.3743 (13)	C8—C9	1.3923 (16)
O1—C2	1.4644 (13)	C8—H8	0.9500
O4—C4	1.2288 (14)	C9—C10	1.4053 (16)
C2—C12	1.5148 (15)	C9—H9	0.9500
C2—C3	1.5367 (16)	C12—C13	1.4060 (16)
C2—H2	1.0000	C12—C17	1.4069 (16)
C3—C4	1.5212 (15)	C13—C14	1.3977 (16)
C3—H3A	0.9900	C13—H13	0.9500
C3—H3B	0.9900	C14—C15	1.4064 (16)
C4—C5	1.4899 (15)	C14—H14	0.9500
C5—C6	1.4090 (16)	C15—C16	1.3969 (17)
C5—C10	1.4174 (16)	C16—C17	1.3960 (16)
C6—C7	1.3908 (16)	C16—H16	0.9500
C6—H6	0.9500	C17—H17	0.9500
C7—C8	1.4121 (17)
C10—O1—C2	113.30 (8)	C9—C8—H8	119.3
O1—C2—C12	107.76 (9)	C7—C8—H8	119.3
O1—C2—C3	109.86 (9)	C8—C9—C10	118.82 (11)
C12—C2—C3	113.03 (9)	C8—C9—H9	120.6
O1—C2—H2	108.7	C10—C9—H9	120.6
C12—C2—H2	108.7	O1—C10—C9	117.12 (10)
C3—C2—H2	108.7	O1—C10—C5	122.32 (10)
C4—C3—C2	111.15 (9)	C9—C10—C5	120.56 (10)
C4—C3—H3A	109.4	C13—C12—C17	119.75 (10)
C2—C3—H3A	109.4	C13—C12—C2	120.85 (10)
C4—C3—H3B	109.4	C17—C12—C2	119.34 (10)
C2—C3—H3B	109.4	C14—C13—C12	120.29 (10)
H3A—C3—H3B	108.0	C14—C13—H13	119.9
O4—C4—C5	122.64 (10)	C12—C13—H13	119.9
O4—C4—C3	122.77 (10)	C13—C14—C15	118.61 (10)
C5—C4—C3	114.52 (10)	C13—C14—H14	120.7
C6—C5—C10	119.33 (10)	C15—C14—H14	120.7
C6—C5—C4	120.16 (10)	C16—C15—C14	122.15 (10)
C10—C5—C4	120.26 (10)	C16—C15—Cl1	118.95 (9)
C7—C6—C5	120.23 (11)	C14—C15—Cl1	118.90 (9)
C7—C6—H6	119.9	C17—C16—C15	118.39 (10)
C5—C6—H6	119.9	C17—C16—H16	120.8
C6—C7—C8	119.60 (10)	C15—C16—H16	120.8
C6—C7—H7	120.2	C16—C17—C12	120.79 (10)
C8—C7—H7	120.2	C16—C17—H17	119.6
C9—C8—C7	121.33 (10)	C12—C17—H17	119.6
C10—O1—C2—C12	−179.63 (9)	C6—C5—C10—O1	176.64 (10)
C10—O1—C2—C3	56.83 (11)	C4—C5—C10—O1	−9.05 (16)
O1—C2—C3—C4	−57.46 (12)	C6—C5—C10—C9	−4.14 (16)
C12—C2—C3—C4	−177.86 (9)	C4—C5—C10—C9	170.18 (10)
C2—C3—C4—O4	−157.39 (11)	O1—C2—C12—C13	−49.03 (13)
C2—C3—C4—C5	25.82 (13)	C3—C2—C12—C13	72.56 (13)
O4—C4—C5—C6	4.15 (17)	O1—C2—C12—C17	133.56 (10)
C3—C4—C5—C6	−179.05 (10)	C3—C2—C12—C17	−104.85 (12)
O4—C4—C5—C10	−170.11 (11)	C17—C12—C13—C14	0.34 (17)
C3—C4—C5—C10	6.69 (15)	C2—C12—C13—C14	−177.06 (10)
C10—C5—C6—C7	1.94 (16)	C12—C13—C14—C15	0.80 (17)
C4—C5—C6—C7	−172.38 (10)	C13—C14—C15—C16	−1.38 (17)
C5—C6—C7—C8	1.24 (17)	C13—C14—C15—Cl1	178.82 (8)
C6—C7—C8—C9	−2.34 (17)	C14—C15—C16—C17	0.77 (17)
C7—C8—C9—C10	0.17 (17)	Cl1—C15—C16—C17	−179.43 (8)
C2—O1—C10—C9	156.80 (10)	C15—C16—C17—C12	0.42 (16)
C2—O1—C10—C5	−23.95 (14)	C13—C12—C17—C16	−0.97 (17)
C8—C9—C10—O1	−177.67 (9)	C2—C12—C17—C16	176.47 (10)
C8—C9—C10—C5	3.07 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—Cl1···O4^i	1.75	3.05 (1)	4.798 (2)	175

Symmetry code: (i) −x+2, y−1/2, −z+1/2.

8-Bromo-6-methyl-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one (FL8)

Crystal data

C16H13BrO2	F(000) = 1280
Mr = 317.17	Dx = 1.527 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 15.2121 (7) Å	Cell parameters from 11075 reflections
b = 8.7614 (2) Å	θ = 3.3–39.1°
c = 20.7260 (6) Å	µ = 2.97 mm^−1
β = 92.458 (3)°	T = 100 K
V = 2759.81 (16) Å^3	Prism, colourless
Z = 8	0.2 × 0.1 × 0.1 mm

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas detector	5682 independent reflections
Mirror monochromator	4561 reflections with I > 2σ(I)
Detector resolution: 10.4498 pixels mm^-1	Rint = 0.051
ω scans	θmax = 26.5°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −19→19
Tmin = 0.524, Tmax = 1.000	k = −8→11
30046 measured reflections	l = −26→26

Refinement

Refinement on F^2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0254P)^2 + 3.6602P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
5682 reflections	Δρmax = 0.98 e Å^−3
351 parameters	Δρmin = −0.61 e Å^−3
6 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.

Refinement. Single-crystal X-ray data of five flavanone derivatives (FL1, FL2, FL3, FL5 and FL8) were collected on a micro-focus SuperNova diffractometer with an Atlas detector, whereas data collection of two chalcone derivatives (CH2 and CH4) was carried out on an Xcalibur diffractometer with a Sapphire3 detector; all using Mo Kα and ω scans at a low temperature of 100.0 (1) K. The X-ray data were corrected for absorption using CrysAlis PRO (Agilent, 2015). All structures were solved using SHELXT (Sheldrick, 2015a) and refined with SHELXL2014/7 (Sheldrick, 2015b). All non-H atoms were refined anisotropically.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	0.10490 (2)	0.35851 (4)	−0.03593 (2)	0.02302 (10)
O1	0.12423 (15)	0.6946 (2)	−0.02408 (11)	0.0203 (5)
O4	0.21704 (18)	0.9584 (3)	0.12826 (12)	0.0325 (6)
C2A	0.1526 (3)	0.8513 (4)	−0.03329 (19)	0.0250 (10)	0.928 (7)
H2A	0.2174	0.8509	−0.0397	0.030*	0.928 (7)
C2B	0.0922 (7)	0.8509 (7)	−0.0271 (3)	0.0250 (10)	0.072 (7)
H2B	0.0274	0.8494	−0.0205	0.030*	0.072 (7)
C3	0.1356 (3)	0.9446 (4)	0.02593 (18)	0.0352 (10)
H3A	0.0717	0.9462	0.0330	0.042*	0.928 (7)
H3B	0.1551	1.0509	0.0191	0.042*	0.928 (7)
H3C	0.0893	1.0122	0.0421	0.042*	0.072 (7)
H3D	0.1781	1.0118	0.0049	0.042*	0.072 (7)
C4	0.1838 (2)	0.8797 (4)	0.08504 (17)	0.0262 (8)
C5	0.1848 (2)	0.7105 (4)	0.08718 (16)	0.0206 (7)
C6	0.2153 (2)	0.6325 (4)	0.14264 (17)	0.0236 (7)
H6	0.2375	0.6893	0.1788	0.028*
C7	0.2142 (2)	0.4748 (4)	0.14611 (17)	0.0246 (8)
C8	0.1805 (2)	0.3952 (4)	0.09186 (17)	0.0230 (7)
H8	0.1791	0.2869	0.0929	0.028*
C9	0.1492 (2)	0.4700 (4)	0.03698 (16)	0.0198 (7)
C10	0.1520 (2)	0.6292 (4)	0.03300 (16)	0.0187 (7)
C11	0.2476 (3)	0.3887 (4)	0.20639 (18)	0.0316 (9)
H11A	0.2985	0.4425	0.2261	0.047*
H11B	0.2651	0.2852	0.1944	0.047*
H11C	0.2008	0.3832	0.2373	0.047*
C12	0.1066 (2)	0.9125 (4)	−0.09402 (18)	0.0269 (8)
C13	0.0252 (2)	0.8560 (4)	−0.11740 (18)	0.0282 (8)
H13	−0.0024	0.7747	−0.0957	0.034*
C14	−0.0148 (3)	0.9195 (4)	−0.17251 (19)	0.0328 (9)
H14	−0.0698	0.8809	−0.1887	0.039*
C15	0.0252 (3)	1.0397 (4)	−0.20416 (19)	0.0345 (9)
H15	−0.0025	1.0830	−0.2418	0.041*
C16	0.1058 (3)	1.0962 (4)	−0.18056 (19)	0.0334 (9)
H16	0.1330	1.1787	−0.2018	0.040*
C17	0.1463 (2)	1.0316 (4)	−0.12600 (19)	0.0300 (8)
H17	0.2017	1.0692	−0.1103	0.036*
Br51	0.45390 (2)	0.63182 (4)	0.14107 (2)	0.02582 (10)
O51	0.45483 (15)	0.2913 (2)	0.12764 (11)	0.0237 (5)
O54	0.35363 (18)	0.0195 (3)	−0.01903 (14)	0.0386 (7)
C52A	0.4912 (3)	0.1394 (4)	0.1183 (2)	0.0285 (11)	0.814 (7)
H52A	0.5425	0.1486	0.0901	0.034*	0.814 (7)
C52B	0.4432 (6)	0.1313 (7)	0.1436 (4)	0.0285 (11)	0.186 (7)
H52B	0.3912	0.1231	0.1713	0.034*	0.186 (7)
C53	0.4256 (3)	0.0381 (5)	0.0861 (2)	0.0475 (12)
H53A	0.3778	0.0187	0.1159	0.057*	0.814 (7)
H53B	0.4539	−0.0610	0.0772	0.057*	0.814 (7)
H53C	0.3866	−0.0459	0.0991	0.057*	0.186 (7)
H53D	0.4823	−0.0096	0.0756	0.057*	0.186 (7)
C54	0.3862 (2)	0.1013 (4)	0.0237 (2)	0.0329 (9)
C55	0.3877 (2)	0.2694 (4)	0.01884 (17)	0.0234 (8)
C56	0.3559 (2)	0.3434 (4)	−0.03726 (18)	0.0267 (8)
H56	0.3352	0.2839	−0.0731	0.032*
C57	0.3537 (2)	0.5005 (4)	−0.04204 (17)	0.0256 (8)
C58	0.3827 (2)	0.5846 (4)	0.01242 (17)	0.0238 (8)
H58	0.3802	0.6929	0.0109	0.029*
C59	0.4149 (2)	0.5144 (4)	0.06800 (17)	0.0220 (7)
C60	0.4197 (2)	0.3556 (4)	0.07230 (16)	0.0217 (7)
C61	0.3225 (2)	0.5775 (4)	−0.10422 (18)	0.0319 (9)
H61A	0.3722	0.5897	−0.1324	0.048*
H61B	0.2981	0.6781	−0.0945	0.048*
H61C	0.2770	0.5148	−0.1261	0.048*
C62	0.5246 (3)	0.0814 (4)	0.1842 (2)	0.0427 (11)
C63	0.4734 (3)	0.0766 (4)	0.2407 (2)	0.0390 (10)
H63	0.4146	0.1133	0.2389	0.047*
C64	0.5102 (3)	0.0180 (4)	0.2978 (2)	0.0348 (9)
H64	0.4773	0.0150	0.3357	0.042*
C65	0.5962 (2)	−0.0363 (4)	0.29866 (19)	0.0309 (9)
H65	0.6218	−0.0772	0.3375	0.037*
C66	0.6457 (3)	−0.0318 (5)	0.2434 (2)	0.0455 (11)
H66	0.7042	−0.0702	0.2450	0.055*
C67	0.6103 (3)	0.0279 (5)	0.1867 (2)	0.0500 (12)
H67	0.6444	0.0323	0.1494	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0318 (2)	0.01882 (17)	0.01830 (19)	−0.00322 (13)	−0.00003 (13)	−0.00123 (13)
O1	0.0284 (13)	0.0174 (11)	0.0151 (13)	0.0001 (9)	0.0003 (9)	0.0000 (9)
O4	0.0478 (16)	0.0278 (13)	0.0215 (15)	−0.0042 (12)	−0.0022 (12)	−0.0075 (11)
C2A	0.031 (2)	0.0170 (18)	0.027 (2)	−0.0013 (15)	−0.0029 (16)	−0.0036 (16)
C2B	0.031 (2)	0.0170 (18)	0.027 (2)	−0.0013 (15)	−0.0029 (16)	−0.0036 (16)
C3	0.062 (3)	0.0211 (19)	0.022 (2)	0.0031 (18)	−0.0053 (18)	−0.0036 (16)
C4	0.034 (2)	0.0259 (19)	0.0187 (19)	0.0010 (15)	0.0027 (15)	−0.0058 (15)
C5	0.0242 (17)	0.0217 (17)	0.0161 (18)	0.0023 (13)	0.0024 (13)	−0.0024 (14)
C6	0.0247 (17)	0.0267 (18)	0.0192 (19)	0.0025 (14)	−0.0006 (13)	−0.0047 (15)
C7	0.0255 (18)	0.0300 (19)	0.0183 (19)	0.0044 (15)	0.0011 (14)	0.0006 (15)
C8	0.0262 (18)	0.0186 (16)	0.025 (2)	0.0021 (14)	0.0044 (14)	0.0032 (15)
C9	0.0232 (17)	0.0204 (16)	0.0161 (18)	0.0014 (13)	0.0046 (13)	−0.0041 (14)
C10	0.0206 (16)	0.0220 (16)	0.0139 (17)	0.0021 (13)	0.0034 (12)	0.0005 (14)
C11	0.038 (2)	0.038 (2)	0.018 (2)	0.0067 (17)	−0.0038 (15)	0.0013 (17)
C12	0.038 (2)	0.0194 (17)	0.023 (2)	0.0016 (15)	−0.0017 (15)	−0.0054 (15)
C13	0.040 (2)	0.0237 (18)	0.021 (2)	−0.0016 (15)	0.0020 (15)	−0.0004 (15)
C14	0.035 (2)	0.034 (2)	0.029 (2)	0.0016 (17)	−0.0055 (16)	−0.0006 (18)
C15	0.053 (3)	0.032 (2)	0.017 (2)	0.0031 (18)	−0.0041 (17)	0.0005 (17)
C16	0.050 (2)	0.0263 (19)	0.024 (2)	−0.0043 (17)	0.0039 (17)	0.0005 (16)
C17	0.036 (2)	0.0218 (18)	0.031 (2)	−0.0011 (15)	−0.0020 (16)	−0.0051 (16)
Br51	0.0314 (2)	0.02158 (18)	0.0242 (2)	0.00053 (14)	−0.00135 (14)	−0.00126 (15)
O51	0.0310 (13)	0.0189 (12)	0.0208 (14)	0.0009 (10)	−0.0016 (10)	0.0010 (10)
O54	0.0484 (17)	0.0310 (14)	0.0354 (18)	−0.0056 (12)	−0.0088 (13)	−0.0103 (13)
C52A	0.041 (3)	0.022 (2)	0.022 (3)	0.006 (2)	0.0052 (18)	−0.0015 (19)
C52B	0.041 (3)	0.022 (2)	0.022 (3)	0.006 (2)	0.0052 (18)	−0.0015 (19)
C53	0.060 (3)	0.027 (2)	0.052 (3)	−0.0001 (19)	−0.032 (2)	−0.001 (2)
C54	0.034 (2)	0.0276 (19)	0.037 (2)	−0.0003 (16)	−0.0037 (17)	−0.0038 (18)
C55	0.0222 (17)	0.0243 (18)	0.024 (2)	−0.0012 (14)	0.0030 (14)	−0.0012 (15)
C56	0.0231 (18)	0.034 (2)	0.023 (2)	−0.0043 (15)	0.0023 (14)	−0.0034 (16)
C57	0.0210 (18)	0.035 (2)	0.021 (2)	0.0010 (15)	0.0019 (14)	0.0042 (16)
C58	0.0217 (17)	0.0250 (18)	0.025 (2)	0.0016 (14)	0.0028 (14)	0.0035 (15)
C59	0.0206 (17)	0.0217 (17)	0.024 (2)	−0.0001 (13)	0.0031 (14)	−0.0016 (15)
C60	0.0221 (17)	0.0256 (18)	0.0177 (18)	0.0004 (14)	0.0037 (13)	0.0000 (15)
C61	0.030 (2)	0.037 (2)	0.028 (2)	0.0028 (16)	−0.0032 (16)	0.0064 (18)
C62	0.085 (3)	0.0183 (18)	0.024 (2)	0.001 (2)	−0.009 (2)	0.0014 (17)
C63	0.041 (2)	0.029 (2)	0.046 (3)	0.0042 (17)	−0.0088 (19)	0.0052 (19)
C64	0.037 (2)	0.041 (2)	0.026 (2)	−0.0038 (18)	0.0013 (16)	0.0064 (18)
C65	0.035 (2)	0.033 (2)	0.024 (2)	−0.0019 (16)	−0.0039 (16)	0.0066 (17)
C66	0.056 (3)	0.050 (3)	0.031 (3)	0.011 (2)	0.010 (2)	0.002 (2)
C67	0.082 (4)	0.040 (2)	0.029 (3)	0.013 (2)	0.014 (2)	0.001 (2)

Geometric parameters (Å, º)

Br1—C9	1.898 (3)	Br51—C59	1.904 (3)
O1—C10	1.365 (4)	O51—C60	1.366 (4)
O1—C2A	1.454 (4)	O51—C52B	1.454 (6)
O1—C2B	1.454 (6)	O51—C52A	1.458 (4)
O4—C4	1.222 (4)	O54—C54	1.227 (4)
C2A—C3	1.506 (5)	C52A—C53	1.473 (5)
C2A—C12	1.512 (5)	C52A—C62	1.523 (6)
C2A—H2A	1.0000	C52A—H52A	1.0000
C2B—C3	1.502 (7)	C52B—C53	1.460 (7)
C2B—C12	1.513 (7)	C52B—C62	1.530 (7)
C2B—H2B	1.0000	C52B—H52B	1.0000
C3—C4	1.511 (5)	C53—C54	1.508 (5)
C3—H3A	0.9900	C53—H53A	0.9900
C3—H3B	0.9900	C53—H53B	0.9900
C3—H3C	0.9900	C53—H53C	0.9900
C3—H3D	0.9900	C53—H53D	0.9900
C4—C5	1.483 (5)	C54—C55	1.477 (5)
C5—C6	1.400 (5)	C55—C56	1.400 (5)
C5—C10	1.403 (4)	C55—C60	1.411 (5)
C6—C7	1.384 (5)	C56—C57	1.380 (5)
C6—H6	0.9500	C56—H56	0.9500
C7—C8	1.401 (5)	C57—C58	1.404 (5)
C7—C11	1.528 (5)	C57—C61	1.513 (5)
C8—C9	1.379 (5)	C58—C59	1.377 (5)
C8—H8	0.9500	C58—H58	0.9500
C9—C10	1.398 (4)	C59—C60	1.396 (5)
C11—H11A	0.9800	C61—H61A	0.9800
C11—H11B	0.9800	C61—H61B	0.9800
C11—H11C	0.9800	C61—H61C	0.9800
C12—C17	1.388 (5)	C62—C67	1.384 (6)
C12—C13	1.400 (5)	C62—C63	1.434 (6)
C13—C14	1.388 (5)	C63—C64	1.387 (5)
C13—H13	0.9500	C63—H63	0.9500
C14—C15	1.395 (5)	C64—C65	1.391 (5)
C14—H14	0.9500	C64—H64	0.9500
C15—C16	1.391 (5)	C65—C66	1.399 (6)
C15—H15	0.9500	C65—H65	0.9500
C16—C17	1.385 (5)	C66—C67	1.375 (6)
C16—H16	0.9500	C66—H66	0.9500
C17—H17	0.9500	C67—H67	0.9500
C10—O1—C2A	115.3 (3)	C60—O51—C52B	122.9 (3)
C10—O1—C2B	121.6 (3)	C60—O51—C52A	113.7 (3)
O1—C2A—C3	110.1 (3)	O51—C52A—C53	110.9 (3)
O1—C2A—C12	108.4 (3)	O51—C52A—C62	107.5 (3)
C3—C2A—C12	113.4 (3)	C53—C52A—C62	113.5 (3)
O1—C2A—H2A	108.3	O51—C52A—H52A	108.3
C3—C2A—H2A	108.3	C53—C52A—H52A	108.3
C12—C2A—H2A	108.3	C62—C52A—H52A	108.3
O1—C2B—C3	110.3 (5)	O51—C52B—C53	111.9 (5)
O1—C2B—C12	108.3 (5)	O51—C52B—C62	107.3 (5)
C3—C2B—C12	113.5 (5)	C53—C52B—C62	113.9 (5)
O1—C2B—H2B	108.2	O51—C52B—H52B	107.8
C3—C2B—H2B	108.2	C53—C52B—H52B	107.8
C12—C2B—H2B	108.2	C62—C52B—H52B	107.8
C2B—C3—C4	124.8 (4)	C52B—C53—C54	123.2 (4)
C2A—C3—C4	111.2 (3)	C52A—C53—C54	113.9 (3)
C2A—C3—H3A	109.4	C52A—C53—H53A	108.8
C4—C3—H3A	109.4	C54—C53—H53A	108.8
C2A—C3—H3B	109.4	C52A—C53—H53B	108.8
C4—C3—H3B	109.4	C54—C53—H53B	108.8
H3A—C3—H3B	108.0	H53A—C53—H53B	107.7
C2B—C3—H3C	106.1	C52B—C53—H53C	106.5
C4—C3—H3C	106.1	C54—C53—H53C	106.5
C2B—C3—H3D	106.1	C52B—C53—H53D	106.5
C4—C3—H3D	106.1	C54—C53—H53D	106.5
H3C—C3—H3D	106.3	H53C—C53—H53D	106.5
O4—C4—C5	122.6 (3)	O54—C54—C55	122.7 (4)
O4—C4—C3	123.5 (3)	O54—C54—C53	122.6 (3)
C5—C4—C3	113.8 (3)	C55—C54—C53	114.7 (3)
C6—C5—C10	120.2 (3)	C56—C55—C60	120.0 (3)
C6—C5—C4	121.0 (3)	C56—C55—C54	120.9 (3)
C10—C5—C4	118.7 (3)	C60—C55—C54	119.1 (3)
C7—C6—C5	121.7 (3)	C57—C56—C55	121.9 (3)
C7—C6—H6	119.2	C57—C56—H56	119.1
C5—C6—H6	119.2	C55—C56—H56	119.1
C6—C7—C8	117.4 (3)	C56—C57—C58	117.4 (3)
C6—C7—C11	122.1 (3)	C56—C57—C61	120.8 (3)
C8—C7—C11	120.5 (3)	C58—C57—C61	121.8 (3)
C9—C8—C7	121.8 (3)	C59—C58—C57	121.8 (3)
C9—C8—H8	119.1	C59—C58—H58	119.1
C7—C8—H8	119.1	C57—C58—H58	119.1
C8—C9—C10	120.8 (3)	C58—C59—C60	120.9 (3)
C8—C9—Br1	120.7 (2)	C58—C59—Br51	120.8 (3)
C10—C9—Br1	118.5 (3)	C60—C59—Br51	118.3 (3)
O1—C10—C9	117.5 (3)	O51—C60—C59	118.8 (3)
O1—C10—C5	124.5 (3)	O51—C60—C55	123.2 (3)
C9—C10—C5	118.0 (3)	C59—C60—C55	117.9 (3)
C7—C11—H11A	109.5	C57—C61—H61A	109.5
C7—C11—H11B	109.5	C57—C61—H61B	109.5
H11A—C11—H11B	109.5	H61A—C61—H61B	109.5
C7—C11—H11C	109.5	C57—C61—H61C	109.5
H11A—C11—H11C	109.5	H61A—C61—H61C	109.5
H11B—C11—H11C	109.5	H61B—C61—H61C	109.5
C17—C12—C13	119.8 (3)	C67—C62—C63	120.2 (4)
C17—C12—C2A	118.0 (3)	C67—C62—C52A	115.0 (4)
C13—C12—C2A	122.2 (3)	C63—C62—C52A	124.7 (4)
C17—C12—C2B	142.1 (4)	C67—C62—C52B	148.8 (5)
C13—C12—C2B	91.7 (4)	C63—C62—C52B	90.1 (5)
C14—C13—C12	119.6 (3)	C64—C63—C62	119.6 (4)
C14—C13—H13	120.2	C64—C63—H63	120.2
C12—C13—H13	120.2	C62—C63—H63	120.2
C13—C14—C15	120.3 (4)	C63—C64—C65	118.8 (4)
C13—C14—H14	119.9	C63—C64—H64	120.6
C15—C14—H14	119.9	C65—C64—H64	120.6
C16—C15—C14	120.0 (4)	C64—C65—C66	121.3 (4)
C16—C15—H15	120.0	C64—C65—H65	119.4
C14—C15—H15	120.0	C66—C65—H65	119.4
C17—C16—C15	119.7 (4)	C67—C66—C65	120.4 (4)
C17—C16—H16	120.1	C67—C66—H66	119.8
C15—C16—H16	120.1	C65—C66—H66	119.8
C16—C17—C12	120.7 (3)	C66—C67—C62	119.7 (4)
C16—C17—H17	119.7	C66—C67—H67	120.2
C12—C17—H17	119.7	C62—C67—H67	120.2
C10—O1—C2A—C3	−48.0 (4)	C60—O51—C52A—C53	−53.5 (4)
C10—O1—C2A—C12	−172.5 (3)	C60—O51—C52A—C62	−178.1 (3)
C10—O1—C2B—C3	29.4 (8)	C60—O51—C52B—C53	24.6 (8)
C10—O1—C2B—C12	154.2 (4)	C60—O51—C52B—C62	150.2 (4)
O1—C2B—C3—C4	−16.9 (8)	O51—C52B—C53—C54	−24.5 (8)
C12—C2B—C3—C4	−138.6 (5)	C62—C52B—C53—C54	−146.5 (5)
O1—C2A—C3—C4	59.1 (4)	O51—C52A—C53—C54	53.7 (5)
C12—C2A—C3—C4	−179.4 (3)	C62—C52A—C53—C54	174.8 (4)
C2B—C3—C4—O4	−178.4 (5)	C52B—C53—C54—O54	−163.3 (5)
C2A—C3—C4—O4	143.3 (4)	C52A—C53—C54—O54	156.3 (4)
C2B—C3—C4—C5	−0.3 (6)	C52B—C53—C54—C55	15.2 (7)
C2A—C3—C4—C5	−38.6 (5)	C52A—C53—C54—C55	−25.3 (5)
O4—C4—C5—C6	7.3 (5)	O54—C54—C55—C56	−3.7 (6)
C3—C4—C5—C6	−170.7 (3)	C53—C54—C55—C56	177.9 (4)
O4—C4—C5—C10	−174.5 (3)	O54—C54—C55—C60	174.8 (4)
C3—C4—C5—C10	7.5 (5)	C53—C54—C55—C60	−3.7 (5)
C10—C5—C6—C7	−0.2 (5)	C60—C55—C56—C57	−0.8 (5)
C4—C5—C6—C7	178.0 (3)	C54—C55—C56—C57	177.6 (3)
C5—C6—C7—C8	−0.4 (5)	C55—C56—C57—C58	−1.6 (5)
C5—C6—C7—C11	179.8 (3)	C55—C56—C57—C61	177.4 (3)
C6—C7—C8—C9	−0.3 (5)	C56—C57—C58—C59	2.0 (5)
C11—C7—C8—C9	179.5 (3)	C61—C57—C58—C59	−177.0 (3)
C7—C8—C9—C10	1.5 (5)	C57—C58—C59—C60	0.0 (5)
C7—C8—C9—Br1	179.5 (3)	C57—C58—C59—Br51	179.9 (3)
C2A—O1—C10—C9	−161.9 (3)	C52B—O51—C60—C59	164.2 (5)
C2B—O1—C10—C9	155.8 (5)	C52A—O51—C60—C59	−155.1 (3)
C2A—O1—C10—C5	16.6 (4)	C52B—O51—C60—C55	−15.7 (6)
C2B—O1—C10—C5	−25.6 (6)	C52A—O51—C60—C55	25.1 (4)
C8—C9—C10—O1	176.6 (3)	C58—C59—C60—O51	177.8 (3)
Br1—C9—C10—O1	−1.4 (4)	Br51—C59—C60—O51	−2.2 (4)
C8—C9—C10—C5	−2.1 (5)	C58—C59—C60—C55	−2.3 (5)
Br1—C9—C10—C5	179.9 (2)	Br51—C59—C60—C55	177.7 (2)
C6—C5—C10—O1	−177.1 (3)	C56—C55—C60—O51	−177.4 (3)
C4—C5—C10—O1	4.7 (5)	C54—C55—C60—O51	4.2 (5)
C6—C5—C10—C9	1.4 (5)	C56—C55—C60—C59	2.7 (5)
C4—C5—C10—C9	−176.8 (3)	C54—C55—C60—C59	−175.7 (3)
O1—C2A—C12—C17	−155.4 (3)	O51—C52A—C62—C67	−128.6 (4)
C3—C2A—C12—C17	82.1 (4)	C53—C52A—C62—C67	108.4 (5)
O1—C2A—C12—C13	26.4 (5)	O51—C52A—C62—C63	52.8 (5)
C3—C2A—C12—C13	−96.1 (4)	C53—C52A—C62—C63	−70.2 (5)
O1—C2B—C12—C17	−124.3 (6)	O51—C52B—C62—C67	−85.1 (9)
C3—C2B—C12—C17	−1.5 (10)	C53—C52B—C62—C67	39.3 (11)
O1—C2B—C12—C13	87.7 (6)	O51—C52B—C62—C63	107.7 (5)
C3—C2B—C12—C13	−149.4 (6)	C53—C52B—C62—C63	−127.9 (6)
C17—C12—C13—C14	0.2 (5)	C67—C62—C63—C64	0.1 (6)
C2A—C12—C13—C14	178.4 (3)	C52A—C62—C63—C64	178.5 (4)
C2B—C12—C13—C14	158.1 (4)	C52B—C62—C63—C64	172.5 (4)
C12—C13—C14—C15	−0.5 (6)	C62—C63—C64—C65	−0.6 (6)
C13—C14—C15—C16	0.1 (6)	C63—C64—C65—C66	0.4 (6)
C14—C15—C16—C17	0.6 (6)	C64—C65—C66—C67	0.5 (7)
C15—C16—C17—C12	−1.0 (6)	C65—C66—C67—C62	−1.1 (7)
C13—C12—C17—C16	0.6 (5)	C63—C62—C67—C66	0.8 (7)
C2A—C12—C17—C16	−177.7 (3)	C52A—C62—C67—C66	−177.8 (4)
C2B—C12—C17—C16	−141.8 (7)	C52B—C62—C67—C66	−164.4 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2A—H2A···O54^i	1.00	2.57	3.396 (5)	140
C53—H53A···O4^ii	0.99	2.53	3.399 (5)	147

Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z.

(2E)-1-(2-Hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one (CH2)

Crystal data

C16H14O3	Dx = 1.305 Mg m^−3
Mr = 254.29	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 3822 reflections
a = 25.297 (2) Å	θ = 2.9–34.8°
b = 4.0469 (2) Å	µ = 0.09 mm^−1
c = 12.6390 (16) Å	T = 100 K
V = 1293.9 (2) Å^3	Prism, colourless
Z = 4	0.40 × 0.18 × 0.08 mm
F(000) = 536

Data collection

Rigaku Xcalibur with a Sapphire3 detector diffractometer	3120 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3037 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 16.0328 pixels mm^-1	θmax = 28.0°, θmin = 3.2°
ω scans	h = −33→33
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −5→3
Tmin = 0.876, Tmax = 1.000	l = −16→16
12934 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.028	w = 1/[σ^2(Fo^2) + (0.0497P)^2 + 0.1568P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.078	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.24 e Å^−3
3120 reflections	Δρmin = −0.14 e Å^−3
174 parameters	Absolute structure: Flack x determined using 1419 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: −0.4 (3)
Primary atom site location: difference Fourier map

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. Single-crystal X-ray data of five flavanone derivatives (FL1, FL2, FL3, FL5 and FL8) were collected on a micro-focus SuperNova diffractometer with an Atlas detector, whereas data collection of two chalcone derivatives (CH2 and CH4) was carried out on an Xcalibur diffractometer with a Sapphire3 detector; all using Mo Kα and ω scans at a low temperature of 100.0 (1) K. The X-ray data were corrected for absorption using CrysAlis PRO (Agilent, 2015). All structures were solved using SHELXT (Sheldrick, 2015a) and refined with SHELXL2014/7 (Sheldrick, 2015b). All non-H atoms were refined anisotropically.

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

	x	y	z	Uiso*/Ueq
O3	0.45856 (4)	0.2351 (3)	0.75652 (9)	0.0193 (2)
C6	0.75837 (6)	0.9372 (4)	1.07608 (12)	0.0139 (3)
O2	0.70171 (4)	0.6401 (3)	1.19355 (9)	0.0205 (3)
C10	0.58134 (6)	0.4571 (4)	0.96645 (11)	0.0145 (3)
C8	0.66886 (6)	0.7043 (4)	1.01849 (12)	0.0161 (3)
H8	0.6743	0.7902	0.9511	0.019*
C7	0.70889 (6)	0.7551 (4)	1.10186 (13)	0.0150 (3)
C11	0.58327 (6)	0.5443 (4)	0.85734 (13)	0.0165 (3)
H11	0.6128	0.6532	0.8307	0.020*
C5	0.76789 (6)	1.0843 (4)	0.97529 (12)	0.0159 (3)
H5	0.7418	1.0724	0.9236	0.019*
C9	0.62419 (6)	0.5320 (4)	1.04038 (13)	0.0159 (3)
H9	0.6204	0.4538	1.1092	0.019*
C1	0.79841 (6)	0.9596 (4)	1.15428 (12)	0.0165 (3)
O1	0.79241 (5)	0.8278 (3)	1.25304 (9)	0.0217 (3)
H1	0.7631	0.7420	1.2578	0.033*
C15	0.53645 (6)	0.2906 (4)	1.00442 (13)	0.0166 (3)
H15	0.5348	0.2309	1.0754	0.020*
C16	0.41216 (6)	0.0671 (4)	0.79472 (14)	0.0190 (3)
H16A	0.4220	−0.1450	0.8225	0.029*
H16B	0.3876	0.0381	0.7376	0.029*
H16C	0.3960	0.1961	0.8496	0.029*
C12	0.54173 (6)	0.4687 (4)	0.79068 (12)	0.0170 (3)
H12	0.5432	0.5285	0.7197	0.020*
C13	0.49699 (6)	0.3008 (4)	0.83009 (12)	0.0151 (3)
C14	0.49415 (6)	0.2126 (4)	0.93768 (13)	0.0163 (3)
H14	0.4645	0.1040	0.9640	0.020*
C2	0.84627 (6)	1.1201 (4)	1.13051 (13)	0.0189 (3)
H2	0.8727	1.1331	1.1815	0.023*
C3	0.85432 (6)	1.2604 (4)	1.03064 (14)	0.0190 (3)
H3	0.8862	1.3655	1.0160	0.023*
C4	0.81513 (6)	1.2451 (4)	0.95223 (13)	0.0178 (3)
H4	0.8206	1.3405	0.8862	0.021*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0134 (5)	0.0272 (6)	0.0172 (5)	−0.0016 (4)	−0.0022 (4)	−0.0004 (5)
C6	0.0116 (6)	0.0172 (6)	0.0129 (6)	0.0020 (5)	0.0001 (5)	−0.0030 (5)
O2	0.0161 (5)	0.0311 (6)	0.0144 (5)	−0.0010 (5)	0.0000 (4)	0.0023 (5)
C10	0.0124 (6)	0.0159 (6)	0.0152 (7)	0.0013 (5)	0.0001 (5)	−0.0015 (5)
C8	0.0140 (7)	0.0206 (7)	0.0138 (7)	0.0009 (5)	−0.0010 (5)	−0.0008 (6)
C7	0.0127 (6)	0.0184 (7)	0.0141 (7)	0.0019 (5)	0.0011 (5)	−0.0022 (5)
C11	0.0136 (6)	0.0190 (7)	0.0170 (7)	−0.0007 (5)	0.0026 (5)	0.0006 (6)
C5	0.0145 (6)	0.0183 (7)	0.0149 (7)	0.0017 (5)	−0.0008 (5)	−0.0017 (6)
C9	0.0152 (7)	0.0181 (7)	0.0144 (6)	0.0015 (5)	−0.0003 (5)	−0.0002 (6)
C1	0.0163 (7)	0.0203 (7)	0.0127 (7)	0.0028 (5)	−0.0002 (5)	−0.0033 (6)
O1	0.0175 (5)	0.0346 (6)	0.0129 (5)	−0.0027 (5)	−0.0024 (4)	0.0004 (5)
C15	0.0164 (7)	0.0194 (7)	0.0141 (7)	0.0001 (5)	0.0008 (6)	0.0009 (6)
C16	0.0128 (6)	0.0213 (7)	0.0229 (8)	−0.0009 (6)	−0.0019 (5)	−0.0018 (6)
C12	0.0149 (7)	0.0221 (7)	0.0140 (7)	0.0020 (5)	0.0007 (5)	0.0017 (6)
C13	0.0126 (6)	0.0159 (6)	0.0167 (7)	0.0018 (5)	−0.0008 (5)	−0.0022 (6)
C14	0.0134 (6)	0.0187 (6)	0.0170 (7)	−0.0005 (5)	0.0009 (6)	−0.0002 (6)
C2	0.0155 (7)	0.0230 (8)	0.0183 (8)	−0.0002 (6)	−0.0039 (5)	−0.0049 (6)
C3	0.0146 (7)	0.0192 (7)	0.0233 (8)	−0.0015 (5)	0.0019 (6)	−0.0029 (6)
C4	0.0178 (7)	0.0185 (7)	0.0172 (7)	0.0005 (5)	0.0023 (6)	0.0006 (6)

Geometric parameters (Å, º)

O3—C13	1.3712 (18)	C1—O1	1.3659 (19)
O3—C16	1.4399 (19)	C1—C2	1.406 (2)
C6—C1	1.418 (2)	O1—H1	0.8200
C6—C5	1.427 (2)	C15—C14	1.399 (2)
C6—C7	1.489 (2)	C15—H15	0.9300
O2—C7	1.262 (2)	C16—H16A	0.9600
C10—C15	1.405 (2)	C16—H16B	0.9600
C10—C11	1.424 (2)	C16—H16C	0.9600
C10—C9	1.463 (2)	C12—C13	1.411 (2)
C8—C9	1.356 (2)	C12—H12	0.9300
C8—C7	1.476 (2)	C13—C14	1.408 (2)
C8—H8	0.9300	C14—H14	0.9300
C11—C12	1.381 (2)	C2—C3	1.399 (2)
C11—H11	0.9300	C2—H2	0.9300
C5—C4	1.391 (2)	C3—C4	1.403 (2)
C5—H5	0.9300	C3—H3	0.9300
C9—H9	0.9300	C4—H4	0.9300
C13—O3—C16	116.24 (12)	C14—C15—H15	119.3
C1—C6—C5	118.37 (13)	C10—C15—H15	119.3
C1—C6—C7	118.66 (14)	O3—C16—H16A	109.5
C5—C6—C7	122.95 (13)	O3—C16—H16B	109.5
C15—C10—C11	118.51 (14)	H16A—C16—H16B	109.5
C15—C10—C9	118.69 (13)	O3—C16—H16C	109.5
C11—C10—C9	122.80 (13)	H16A—C16—H16C	109.5
C9—C8—C7	119.85 (14)	H16B—C16—H16C	109.5
C9—C8—H8	120.1	C11—C12—C13	120.11 (14)
C7—C8—H8	120.1	C11—C12—H12	119.9
O2—C7—C8	120.36 (13)	C13—C12—H12	119.9
O2—C7—C6	120.31 (14)	O3—C13—C14	124.73 (13)
C8—C7—C6	119.32 (14)	O3—C13—C12	115.00 (13)
C12—C11—C10	120.63 (14)	C14—C13—C12	120.26 (14)
C12—C11—H11	119.7	C15—C14—C13	119.10 (14)
C10—C11—H11	119.7	C15—C14—H14	120.4
C4—C5—C6	121.80 (14)	C13—C14—H14	120.4
C4—C5—H5	119.1	C3—C2—C1	120.37 (14)
C6—C5—H5	119.1	C3—C2—H2	119.8
C8—C9—C10	126.41 (14)	C1—C2—H2	119.8
C8—C9—H9	116.8	C2—C3—C4	121.09 (14)
C10—C9—H9	116.8	C2—C3—H3	119.5
O1—C1—C2	118.12 (13)	C4—C3—H3	119.5
O1—C1—C6	122.18 (14)	C5—C4—C3	118.65 (14)
C2—C1—C6	119.70 (14)	C5—C4—H4	120.7
C1—O1—H1	109.5	C3—C4—H4	120.7
C14—C15—C10	121.38 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.80	2.532 (2)	147
C5—H5···O1^i	0.93	2.53	3.364 (5)	150
C9—H9···O2	0.93	2.44	2.790 (2)	103

Symmetry code: (i) −x+3/2, y, z−1/2.

(2E)-1-(2-Hydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (CH4)

Crystal data

C15H12O3	F(000) = 504
Mr = 240.26	Dx = 1.357 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 3.9413 (2) Å	Cell parameters from 4020 reflections
b = 17.3664 (8) Å	θ = 3.1–30.3°
c = 17.2360 (9) Å	µ = 0.09 mm^−1
β = 94.504 (5)°	T = 100 K
V = 1176.10 (10) Å^3	Needle, light yellow
Z = 4	0.50 × 0.08 × 0.06 mm

Data collection

Rigaku Xcalibur with a Sapphire3 detector diffractometer	4835 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4459 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 16.0328 pixels mm^-1	θmax = 26.5°, θmin = 3.3°
ω scans	h = −4→2
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −21→21
Tmin = 0.758, Tmax = 1.000	l = −21→21
9466 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.030	w = 1/[σ^2(Fo^2) + (0.0379P)^2 + 0.027P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.073	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.15 e Å^−3
4835 reflections	Δρmin = −0.16 e Å^−3
329 parameters	Absolute structure: Flack x determined using 1981 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: −0.2 (5)
Primary atom site location: difference Fourier map

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. Single-crystal X-ray data of five flavanone derivatives (FL1, FL2, FL3, FL5 and FL8) were collected on a micro-focus SuperNova diffractometer with an Atlas detector, whereas data collection of two chalcone derivatives (CH2 and CH4) was carried out on an Xcalibur diffractometer with a Sapphire3 detector; all using Mo Kα and ω scans at a low temperature of 100.0 (1) K. The X-ray data were corrected for absorption using CrysAlis PRO (Agilent, 2015). All structures were solved using SHELXT (Sheldrick, 2015a) and refined with SHELXL2014/7 (Sheldrick, 2015b). All non-H atoms were refined anisotropically.

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

	x	y	z	Uiso*/Ueq
C13	0.9411 (5)	0.03886 (12)	0.03812 (12)	0.0169 (4)
O3	0.9956 (4)	−0.03834 (9)	0.02569 (9)	0.0227 (4)
H31	1.0911	−0.0439	−0.0145	0.034*
C15	0.9684 (5)	0.17217 (12)	0.00239 (13)	0.0176 (4)
H15	1.0222	0.2098	−0.0331	0.021*
C7	0.5989 (5)	0.38907 (13)	0.16070 (12)	0.0161 (4)
O1	0.3998 (4)	0.54764 (8)	0.17933 (9)	0.0229 (4)
H1	0.4938	0.5262	0.1444	0.034*
C1	0.3565 (5)	0.49670 (12)	0.23710 (12)	0.0166 (4)
C11	0.7536 (5)	0.13645 (13)	0.12486 (13)	0.0177 (4)
H11	0.6654	0.1498	0.1715	0.021*
O2	0.6684 (4)	0.43589 (9)	0.10800 (9)	0.0211 (3)
C14	1.0210 (5)	0.09514 (12)	−0.01494 (12)	0.0170 (4)
H14	1.1088	0.0814	−0.0615	0.020*
C9	0.7817 (5)	0.27615 (12)	0.08745 (12)	0.0168 (4)
H9	0.8397	0.3106	0.0493	0.020*
C2	0.2079 (5)	0.52406 (12)	0.30296 (13)	0.0195 (5)
H2	0.1403	0.5753	0.3053	0.023*
C12	0.8031 (5)	0.05960 (13)	0.10760 (12)	0.0183 (4)
H12	0.7445	0.0217	0.1422	0.022*
C6	0.4512 (5)	0.41799 (12)	0.23158 (12)	0.0149 (4)
C5	0.4013 (5)	0.37025 (13)	0.29599 (13)	0.0188 (5)
H5	0.4639	0.3187	0.2942	0.023*
C10	0.8353 (5)	0.19456 (12)	0.07252 (12)	0.0154 (4)
C3	0.1617 (5)	0.47520 (13)	0.36434 (13)	0.0200 (5)
H3	0.0629	0.4938	0.4079	0.024*
C8	0.6555 (5)	0.30652 (13)	0.15150 (12)	0.0174 (4)
H8	0.6027	0.2735	0.1913	0.021*
C4	0.2616 (5)	0.39798 (13)	0.36184 (13)	0.0212 (5)
H4	0.2346	0.3656	0.4039	0.025*
C57	0.1018 (5)	0.18931 (13)	0.47758 (13)	0.0184 (4)
O52	−0.0700 (4)	0.24253 (9)	0.44346 (9)	0.0242 (4)
C54	0.5135 (5)	0.00057 (14)	0.42175 (14)	0.0225 (5)
H54	0.6135	−0.0428	0.4456	0.027*
C52	0.3281 (6)	0.07091 (14)	0.30441 (13)	0.0231 (5)
H52	0.3078	0.0742	0.2504	0.028*
C59	0.0571 (5)	0.25093 (13)	0.60366 (13)	0.0188 (4)
H59	−0.0806	0.2858	0.5749	0.023*
C58	0.1765 (5)	0.19171 (13)	0.56340 (13)	0.0189 (4)
H58	0.3038	0.1529	0.5889	0.023*
C55	0.3911 (5)	0.05940 (13)	0.46626 (13)	0.0197 (5)
H55	0.4130	0.0553	0.5202	0.024*
C53	0.4848 (5)	0.00718 (14)	0.34053 (13)	0.0233 (5)
H53	0.5715	−0.0315	0.3104	0.028*
O51	0.0512 (4)	0.19141 (10)	0.31041 (9)	0.0274 (4)
H51	−0.0333	0.2199	0.3416	0.041*
C56	0.2333 (5)	0.12558 (13)	0.43147 (13)	0.0184 (4)
C51	0.2006 (5)	0.13030 (13)	0.34893 (13)	0.0201 (5)
C60	0.1163 (5)	0.26743 (12)	0.68702 (13)	0.0183 (4)
O53	0.3185 (4)	0.32903 (9)	0.92116 (9)	0.0242 (4)
H531	0.2297	0.3703	0.9308	0.036*
C62	0.3580 (5)	0.23908 (13)	0.81908 (13)	0.0197 (4)
H62	0.4764	0.2060	0.8540	0.024*
C64	0.0487 (5)	0.35869 (13)	0.79190 (13)	0.0202 (5)
H64	−0.0381	0.4049	0.8090	0.024*
C65	−0.0099 (5)	0.33729 (13)	0.71422 (13)	0.0197 (4)
H65	−0.1346	0.3697	0.6798	0.024*
C61	0.2975 (5)	0.21824 (13)	0.74172 (13)	0.0191 (5)
H61	0.3770	0.1711	0.7252	0.023*
C63	0.2396 (5)	0.31046 (13)	0.84470 (12)	0.0186 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C13	0.0187 (10)	0.0134 (10)	0.0183 (10)	0.0007 (8)	0.0002 (8)	−0.0032 (8)
O3	0.0352 (9)	0.0136 (8)	0.0207 (8)	0.0014 (7)	0.0107 (7)	−0.0011 (7)
C15	0.0210 (10)	0.0159 (11)	0.0161 (10)	0.0000 (9)	0.0024 (8)	0.0014 (8)
C7	0.0157 (10)	0.0163 (10)	0.0159 (10)	−0.0021 (8)	−0.0017 (8)	−0.0006 (9)
O1	0.0341 (9)	0.0136 (8)	0.0217 (8)	0.0021 (7)	0.0056 (7)	0.0014 (7)
C1	0.0158 (10)	0.0154 (10)	0.0180 (10)	−0.0020 (9)	−0.0015 (8)	−0.0002 (9)
C11	0.0225 (10)	0.0175 (11)	0.0133 (10)	0.0006 (9)	0.0042 (8)	−0.0019 (8)
O2	0.0305 (8)	0.0152 (7)	0.0183 (7)	−0.0003 (7)	0.0065 (6)	0.0008 (6)
C14	0.0215 (11)	0.0176 (11)	0.0120 (10)	0.0022 (9)	0.0029 (8)	−0.0008 (8)
C9	0.0166 (10)	0.0153 (10)	0.0184 (10)	−0.0018 (8)	0.0007 (8)	0.0026 (8)
C2	0.0189 (10)	0.0143 (10)	0.0250 (11)	0.0005 (9)	0.0008 (9)	−0.0044 (9)
C12	0.0244 (10)	0.0162 (11)	0.0146 (10)	−0.0010 (9)	0.0033 (8)	0.0036 (8)
C6	0.0138 (9)	0.0149 (10)	0.0158 (10)	−0.0013 (8)	−0.0005 (8)	−0.0020 (8)
C5	0.0201 (10)	0.0145 (11)	0.0218 (11)	−0.0008 (9)	0.0014 (9)	−0.0002 (8)
C10	0.0149 (9)	0.0152 (10)	0.0160 (10)	−0.0017 (8)	0.0005 (8)	−0.0006 (8)
C3	0.0177 (10)	0.0230 (12)	0.0198 (11)	−0.0042 (9)	0.0036 (9)	−0.0080 (9)
C8	0.0223 (11)	0.0134 (10)	0.0166 (10)	0.0009 (9)	0.0026 (8)	0.0014 (9)
C4	0.0241 (11)	0.0223 (12)	0.0176 (10)	−0.0048 (10)	0.0042 (9)	0.0012 (9)
C57	0.0156 (9)	0.0177 (11)	0.0217 (11)	−0.0045 (9)	0.0009 (8)	0.0009 (9)
O52	0.0300 (8)	0.0182 (8)	0.0239 (8)	0.0022 (7)	−0.0003 (7)	0.0030 (7)
C54	0.0191 (10)	0.0177 (11)	0.0307 (12)	−0.0002 (9)	0.0024 (9)	−0.0002 (10)
C52	0.0248 (11)	0.0262 (12)	0.0189 (11)	−0.0099 (10)	0.0055 (9)	−0.0017 (9)
C59	0.0162 (10)	0.0172 (11)	0.0230 (11)	−0.0007 (9)	0.0016 (8)	0.0009 (9)
C58	0.0180 (10)	0.0180 (11)	0.0206 (10)	0.0004 (9)	0.0017 (8)	0.0025 (9)
C55	0.0171 (10)	0.0217 (12)	0.0205 (11)	−0.0031 (9)	0.0020 (8)	0.0028 (9)
C53	0.0188 (10)	0.0225 (12)	0.0294 (12)	−0.0060 (9)	0.0080 (9)	−0.0073 (10)
O51	0.0410 (9)	0.0205 (8)	0.0202 (8)	−0.0006 (7)	−0.0009 (7)	0.0023 (7)
C56	0.0166 (9)	0.0180 (11)	0.0204 (11)	−0.0051 (9)	0.0012 (8)	−0.0008 (9)
C51	0.0213 (10)	0.0178 (11)	0.0210 (11)	−0.0079 (9)	0.0008 (9)	0.0024 (9)
C60	0.0148 (9)	0.0171 (11)	0.0238 (11)	−0.0012 (9)	0.0055 (8)	−0.0005 (9)
O53	0.0371 (9)	0.0157 (8)	0.0203 (8)	0.0013 (7)	0.0048 (7)	−0.0019 (6)
C62	0.0200 (10)	0.0150 (11)	0.0247 (11)	0.0000 (9)	0.0051 (9)	0.0027 (9)
C64	0.0203 (11)	0.0126 (10)	0.0288 (12)	−0.0007 (8)	0.0073 (9)	−0.0002 (9)
C65	0.0172 (10)	0.0169 (11)	0.0252 (11)	0.0004 (9)	0.0032 (9)	0.0036 (9)
C61	0.0183 (10)	0.0134 (10)	0.0263 (11)	−0.0003 (8)	0.0058 (9)	−0.0023 (9)
C63	0.0212 (10)	0.0153 (10)	0.0200 (11)	−0.0051 (9)	0.0062 (9)	−0.0007 (9)

Geometric parameters (Å, º)

C13—O3	1.377 (3)	C57—O52	1.263 (3)
C13—C14	1.391 (3)	C57—C56	1.480 (3)
C13—C12	1.401 (3)	C57—C58	1.486 (3)
O3—H31	0.8200	C54—C55	1.387 (3)
C15—C14	1.390 (3)	C54—C53	1.400 (3)
C15—C10	1.410 (3)	C54—H54	0.9300
C15—H15	0.9300	C52—C53	1.390 (3)
C7—O2	1.265 (3)	C52—C51	1.402 (3)
C7—C8	1.462 (3)	C52—H52	0.9300
C7—C6	1.482 (3)	C59—C58	1.346 (3)
O1—C1	1.353 (3)	C59—C60	1.466 (3)
O1—H1	0.8200	C59—H59	0.9300
C1—C2	1.401 (3)	C58—H58	0.9300
C1—C6	1.422 (3)	C55—C56	1.417 (3)
C11—C12	1.385 (3)	C55—H55	0.9300
C11—C10	1.408 (3)	C53—H53	0.9300
C11—H11	0.9300	O51—C51	1.361 (3)
C14—H14	0.9300	O51—H51	0.8200
C9—C8	1.353 (3)	C56—C51	1.421 (3)
C9—C10	1.458 (3)	C60—C65	1.406 (3)
C9—H9	0.9300	C60—C61	1.422 (3)
C2—C3	1.379 (3)	O53—C63	1.368 (3)
C2—H2	0.9300	O53—H531	0.8200
C12—H12	0.9300	C62—C61	1.384 (3)
C6—C5	1.412 (3)	C62—C63	1.408 (3)
C5—C4	1.386 (3)	C62—H62	0.9300
C5—H5	0.9300	C64—C65	1.391 (3)
C3—C4	1.399 (3)	C64—C63	1.410 (3)
C3—H3	0.9300	C64—H64	0.9300
C8—H8	0.9300	C65—H65	0.9300
C4—H4	0.9300	C61—H61	0.9300
O3—C13—C14	122.38 (19)	O52—C57—C56	119.64 (19)
O3—C13—C12	117.33 (19)	O52—C57—C58	120.0 (2)
C14—C13—C12	120.29 (19)	C56—C57—C58	120.35 (19)
C13—O3—H31	109.5	C55—C54—C53	119.2 (2)
C14—C15—C10	121.4 (2)	C55—C54—H54	120.4
C14—C15—H15	119.3	C53—C54—H54	120.4
C10—C15—H15	119.3	C53—C52—C51	120.4 (2)
O2—C7—C8	120.60 (18)	C53—C52—H52	119.8
O2—C7—C6	119.70 (19)	C51—C52—H52	119.8
C8—C7—C6	119.68 (18)	C58—C59—C60	128.3 (2)
C1—O1—H1	109.5	C58—C59—H59	115.9
O1—C1—C2	117.37 (19)	C60—C59—H59	115.9
O1—C1—C6	122.03 (19)	C59—C58—C57	119.0 (2)
C2—C1—C6	120.59 (19)	C59—C58—H58	120.5
C12—C11—C10	120.67 (19)	C57—C58—H58	120.5
C12—C11—H11	119.7	C54—C55—C56	121.6 (2)
C10—C11—H11	119.7	C54—C55—H55	119.2
C15—C14—C13	119.31 (19)	C56—C55—H55	119.2
C15—C14—H14	120.3	C52—C53—C54	120.7 (2)
C13—C14—H14	120.3	C52—C53—H53	119.6
C8—C9—C10	126.2 (2)	C54—C53—H53	119.6
C8—C9—H9	116.9	C51—O51—H51	109.5
C10—C9—H9	116.9	C55—C56—C51	118.2 (2)
C3—C2—C1	120.1 (2)	C55—C56—C57	122.7 (2)
C3—C2—H2	119.9	C51—C56—C57	119.12 (19)
C1—C2—H2	119.9	O51—C51—C52	117.8 (2)
C11—C12—C13	120.2 (2)	O51—C51—C56	122.4 (2)
C11—C12—H12	119.9	C52—C51—C56	119.8 (2)
C13—C12—H12	119.9	C65—C60—C61	118.0 (2)
C5—C6—C1	117.28 (19)	C65—C60—C59	117.54 (19)
C5—C6—C7	122.51 (19)	C61—C60—C59	124.44 (19)
C1—C6—C7	120.20 (18)	C63—O53—H531	109.5
C4—C5—C6	121.9 (2)	C61—C62—C63	119.7 (2)
C4—C5—H5	119.0	C61—C62—H62	120.1
C6—C5—H5	119.0	C63—C62—H62	120.1
C11—C10—C15	118.11 (19)	C65—C64—C63	120.2 (2)
C11—C10—C9	122.66 (19)	C65—C64—H64	119.9
C15—C10—C9	119.22 (19)	C63—C64—H64	119.9
C2—C3—C4	120.8 (2)	C64—C65—C60	121.0 (2)
C2—C3—H3	119.6	C64—C65—H65	119.5
C4—C3—H3	119.6	C60—C65—H65	119.5
C9—C8—C7	122.68 (19)	C62—C61—C60	121.4 (2)
C9—C8—H8	118.7	C62—C61—H61	119.3
C7—C8—H8	118.7	C60—C61—H61	119.3
C5—C4—C3	119.3 (2)	O53—C63—C62	116.98 (19)
C5—C4—H4	120.4	O53—C63—C64	123.43 (19)
C3—C4—H4	120.4	C62—C63—C64	119.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.84	2.570 (2)	147
O3—H31···O2^i	0.82	1.96	2.783 (5)	176
O51—H51···O52	0.82	1.82	2.539 (2)	146
O53—H531···O3^ii	0.82	1.99	2.803 (2)	169
C4—H4···O52	0.93	2.57	3.356 (3)	143
C15—H15···O53^iii	0.93	2.53	3.404 (3)	156

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