The relationship between Hirshfeld potential and cytotoxic activity: a study along a series of flavonoid and chromanone derivatives

The present study examines a series of six biologically-active flavonoid and chromanone derivatives by X-ray crystal structure analysis: (E)-3-benzyl­idene-2-phenyl­chroman-4-one, C₂₂H₁₆O₂, I, (E)-3-(4-methyl­benzyl­idene)-2-phenyl­chroman-4-one, C₂₃H₁₈O₂, II, (E)-3-(3-methyl­benzyl­idene)-2-phenyl­chroman-4-one, C₂₃H₁₈O₂, III, (E)-3-(4-meth­oxy­benzyl­idene)-2-phenyl­chroman-4-one, C₂₃H₁₈O₃, IV, (E)-3-benzyl­idenechroman-4-one, C₁₆H₁₂O₂, V, and (E)-3-(4-meth­oxy­benzyl­idene)chroman-4-one, C₁₇H₁₄O₃, VI. The cytotoxic activities of the presented crystal structures have been determined, together with their inter­molecular inter­action preferences and Hirshfeld surface characteristics. An inverse relationship was found between the contribution of C...C close contacts to the Hirshfeld surface and cytotoxic activity against the WM-115 cancer line. Dependence was also observed between the logP value and the percentage contribution of C...H contacts to the Hirshfeld surface.

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015) for compound_I_AAG10, compound_II_AAG9, compound_III_AAG1, compound_V_AAG5; CrysAlis PRO (Agilent, 2013) for compound_IV_AAG2; CrysAlis PRO (Rigaku OD, 2019) for AAG4. Cell refinement: CrysAlis PRO (Rigaku OD, 2015) for compound_I_AAG10, compound_II_AAG9, compound_III_AAG1, compound_V_AAG5; CrysAlis PRO (Agilent, 2013) for compound_IV_AAG2; CrysAlis PRO (Rigaku OD, 2019) for AAG4. Data reduction: CrysAlis PRO (Rigaku OD, 2015) for compound_I_AAG10, compound_II_AAG9, compound_III_AAG1, compound_V_AAG5; CrysAlis PRO (Agilent, 2013) for compound_IV_AAG2; CrysAlis PRO (Rigaku OD, 2019) for AAG4. For all structures, program(s) used to solve structure: SHELXS (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 1999); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) and publCIF (Westrip, 2010).

(E)-3-Benzylidene-2-phenylchroman-4-one (compound_I_AAG10)

Crystal data

C22H16O2	F(000) = 1312
Mr = 312.35	Dx = 1.278 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.2487 (3) Å	Cell parameters from 7518 reflections
b = 16.3033 (4) Å	θ = 3.4–35.7°
c = 19.7539 (7) Å	µ = 0.08 mm^−1
β = 100.420 (3)°	T = 100 K
V = 3246.20 (17) Å^3	Plate, colorless
Z = 8	0.28 × 0.26 × 0.08 mm

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	13340 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	11168 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.042
Detector resolution: 10.4498 pixels mm^-1	θmax = 26.5°, θmin = 3.3°
ω scans	h = −12→9
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −20→20
Tmin = 0.744, Tmax = 1.000	l = −24→24
13340 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.060	H-atom parameters constrained
wR(F^2) = 0.153	w = 1/[σ^2(Fo^2) + (0.060P)^2 + 1.5246P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
13340 reflections	Δρmax = 0.49 e Å^−3
205 parameters	Δρmin = −0.38 e Å^−3

Special details

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

Refinement. Refined as a 2-component perfect twin.

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

	x	y	z	Uiso*/Ueq
O1	0.32317 (14)	0.18634 (9)	0.46640 (7)	0.0255 (4)
O4	0.17916 (15)	0.30418 (10)	0.28534 (9)	0.0375 (4)
C2	0.2187 (2)	0.14416 (13)	0.41919 (11)	0.0226 (4)
H2	0.1530	0.1238	0.4471	0.027*
C3	0.14523 (19)	0.20038 (12)	0.36501 (11)	0.0220 (4)
C4	0.2246 (2)	0.26304 (13)	0.33592 (11)	0.0248 (5)
C5	0.4459 (2)	0.33109 (14)	0.34907 (13)	0.0320 (5)
H5	0.4200	0.3550	0.3048	0.038*
C6	0.5669 (2)	0.35083 (15)	0.38841 (14)	0.0377 (6)
H6	0.6254	0.3871	0.3709	0.045*
C7	0.6030 (2)	0.31731 (14)	0.45384 (14)	0.0350 (6)
H7	0.6850	0.3325	0.4816	0.042*
C8	0.5213 (2)	0.26219 (13)	0.47898 (12)	0.0288 (5)
H8	0.5471	0.2394	0.5237	0.035*
C9	0.40053 (19)	0.24013 (12)	0.43838 (11)	0.0225 (4)
C10	0.36040 (19)	0.27579 (13)	0.37392 (11)	0.0241 (5)
C11	0.01360 (19)	0.19908 (13)	0.34047 (11)	0.0249 (5)
H11	−0.0155	0.2393	0.3063	0.030*
C12	−0.09296 (11)	0.14678 (8)	0.35704 (8)	0.0276 (5)
C13	−0.07390 (11)	0.06755 (9)	0.38294 (8)	0.0342 (6)
H13	0.0124	0.0441	0.3909	0.041*
C14	−0.18105 (15)	0.02267 (8)	0.39717 (9)	0.0425 (6)
H14	−0.1680	−0.0315	0.4149	0.051*
C15	−0.30727 (12)	0.05701 (10)	0.38550 (9)	0.0448 (7)
H15	−0.3805	0.0263	0.3952	0.054*
C16	−0.32633 (10)	0.13624 (10)	0.35960 (8)	0.0412 (6)
H16	−0.4126	0.1597	0.3516	0.049*
C17	−0.21918 (13)	0.18112 (8)	0.34537 (8)	0.0334 (5)
H17	−0.2322	0.2353	0.3277	0.040*
C18	0.27922 (18)	0.06873 (12)	0.39076 (11)	0.0213 (4)
C19	0.34181 (19)	0.01096 (13)	0.43743 (12)	0.0265 (5)
H19	0.3452	0.0193	0.4853	0.032*
C20	0.3992 (2)	−0.05840 (13)	0.41512 (13)	0.0311 (5)
H20	0.4422	−0.0970	0.4477	0.037*
C21	0.3943 (2)	−0.07174 (13)	0.34587 (13)	0.0327 (5)
H21	0.4342	−0.1192	0.3305	0.039*
C22	0.3308 (2)	−0.01541 (15)	0.29893 (13)	0.0362 (6)
H22	0.3261	−0.0244	0.2510	0.043*
C23	0.2737 (2)	0.05466 (14)	0.32169 (12)	0.0302 (5)
H23	0.2304	0.0931	0.2890	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0270 (8)	0.0262 (8)	0.0219 (8)	−0.0036 (6)	0.0005 (6)	−0.0032 (6)
O4	0.0286 (8)	0.0346 (9)	0.0432 (10)	−0.0068 (7)	−0.0099 (7)	0.0148 (8)
C2	0.0199 (10)	0.0250 (11)	0.0225 (10)	−0.0053 (8)	0.0021 (8)	−0.0006 (8)
C3	0.0184 (10)	0.0196 (10)	0.0278 (11)	0.0000 (8)	0.0032 (8)	−0.0022 (8)
C4	0.0195 (10)	0.0221 (10)	0.0310 (12)	0.0009 (8)	−0.0003 (8)	0.0019 (9)
C5	0.0240 (11)	0.0291 (12)	0.0409 (14)	−0.0027 (9)	0.0006 (10)	0.0078 (10)
C6	0.0216 (11)	0.0318 (13)	0.0575 (17)	−0.0062 (10)	0.0013 (11)	0.0059 (11)
C7	0.0211 (11)	0.0277 (12)	0.0512 (15)	−0.0014 (9)	−0.0066 (10)	−0.0053 (10)
C8	0.0283 (11)	0.0240 (11)	0.0307 (12)	0.0019 (9)	−0.0038 (9)	−0.0056 (9)
C9	0.0198 (10)	0.0193 (10)	0.0279 (11)	0.0023 (8)	0.0029 (8)	−0.0040 (8)
C10	0.0161 (10)	0.0232 (10)	0.0317 (12)	0.0005 (8)	0.0008 (8)	0.0000 (8)
C11	0.0202 (10)	0.0246 (11)	0.0296 (11)	0.0000 (8)	0.0037 (9)	−0.0057 (8)
C12	0.0215 (11)	0.0351 (12)	0.0263 (11)	−0.0077 (9)	0.0044 (9)	−0.0101 (9)
C13	0.0268 (12)	0.0421 (14)	0.0351 (13)	−0.0108 (10)	0.0092 (10)	−0.0098 (10)
C14	0.0501 (16)	0.0438 (15)	0.0362 (14)	−0.0207 (12)	0.0143 (12)	−0.0061 (11)
C15	0.0267 (13)	0.075 (2)	0.0351 (14)	−0.0264 (13)	0.0111 (11)	−0.0146 (13)
C16	0.0232 (12)	0.0681 (19)	0.0325 (14)	−0.0093 (11)	0.0056 (10)	−0.0099 (12)
C17	0.0228 (11)	0.0497 (15)	0.0279 (12)	−0.0037 (10)	0.0049 (9)	−0.0109 (10)
C18	0.0162 (9)	0.0191 (10)	0.0276 (11)	−0.0041 (8)	0.0014 (8)	0.0025 (8)
C19	0.0202 (10)	0.0285 (11)	0.0286 (12)	−0.0037 (8)	−0.0012 (8)	0.0054 (9)
C20	0.0194 (10)	0.0219 (11)	0.0470 (14)	−0.0029 (9)	−0.0073 (9)	0.0093 (10)
C21	0.0231 (11)	0.0193 (11)	0.0528 (16)	−0.0017 (9)	−0.0011 (10)	−0.0071 (10)
C22	0.0438 (14)	0.0321 (13)	0.0307 (13)	0.0033 (11)	0.0016 (11)	−0.0072 (10)
C23	0.0354 (12)	0.0238 (11)	0.0291 (12)	0.0059 (9)	0.0000 (9)	0.0036 (9)

Geometric parameters (Å, º)

O1—C9	1.365 (2)	C12—C17	1.3900
O1—C2	1.459 (2)	C13—C14	1.3900
O4—C4	1.223 (3)	C13—H13	0.9500
C2—C3	1.504 (3)	C14—C15	1.3900
C2—C18	1.529 (3)	C14—H14	0.9500
C2—H2	1.0000	C15—C16	1.3900
C3—C11	1.349 (3)	C15—H15	0.9500
C3—C4	1.485 (3)	C16—C17	1.3900
C4—C10	1.472 (3)	C16—H16	0.9500
C5—C6	1.378 (3)	C17—H17	0.9500
C5—C10	1.406 (3)	C18—C23	1.375 (3)
C5—H5	0.9500	C18—C19	1.391 (3)
C6—C7	1.390 (4)	C19—C20	1.383 (3)
C6—H6	0.9500	C19—H19	0.9500
C7—C8	1.381 (3)	C20—C21	1.377 (3)
C7—H7	0.9500	C20—H20	0.9500
C8—C9	1.395 (3)	C21—C22	1.381 (3)
C8—H8	0.9500	C21—H21	0.9500
C9—C10	1.392 (3)	C22—C23	1.395 (3)
C11—C12	1.468 (2)	C22—H22	0.9500
C11—H11	0.9500	C23—H23	0.9500
C12—C13	1.3900
C9—O1—C2	117.18 (16)	C13—C12—C11	124.12 (12)
O1—C2—C3	112.51 (16)	C17—C12—C11	115.88 (12)
O1—C2—C18	108.33 (15)	C14—C13—C12	120.0
C3—C2—C18	114.39 (17)	C14—C13—H13	120.0
O1—C2—H2	107.1	C12—C13—H13	120.0
C3—C2—H2	107.1	C13—C14—C15	120.0
C18—C2—H2	107.1	C13—C14—H14	120.0
C11—C3—C4	117.01 (19)	C15—C14—H14	120.0
C11—C3—C2	125.86 (19)	C14—C15—C16	120.0
C4—C3—C2	117.13 (17)	C14—C15—H15	120.0
O4—C4—C10	121.6 (2)	C16—C15—H15	120.0
O4—C4—C3	122.62 (19)	C17—C16—C15	120.0
C10—C4—C3	115.69 (18)	C17—C16—H16	120.0
C6—C5—C10	120.5 (2)	C15—C16—H16	120.0
C6—C5—H5	119.8	C16—C17—C12	120.0
C10—C5—H5	119.8	C16—C17—H17	120.0
C5—C6—C7	119.6 (2)	C12—C17—H17	120.0
C5—C6—H6	120.2	C23—C18—C19	118.4 (2)
C7—C6—H6	120.2	C23—C18—C2	123.52 (18)
C8—C7—C6	120.9 (2)	C19—C18—C2	118.04 (19)
C8—C7—H7	119.6	C20—C19—C18	120.9 (2)
C6—C7—H7	119.6	C20—C19—H19	119.5
C7—C8—C9	119.6 (2)	C18—C19—H19	119.5
C7—C8—H8	120.2	C21—C20—C19	120.3 (2)
C9—C8—H8	120.2	C21—C20—H20	119.8
O1—C9—C10	122.82 (18)	C19—C20—H20	119.8
O1—C9—C8	116.91 (19)	C20—C21—C22	119.3 (2)
C10—C9—C8	120.2 (2)	C20—C21—H21	120.3
C9—C10—C5	119.17 (19)	C22—C21—H21	120.3
C9—C10—C4	120.21 (19)	C21—C22—C23	120.2 (2)
C5—C10—C4	120.3 (2)	C21—C22—H22	119.9
C3—C11—C12	131.7 (2)	C23—C22—H22	119.9
C3—C11—H11	114.2	C18—C23—C22	120.8 (2)
C12—C11—H11	114.2	C18—C23—H23	119.6
C13—C12—C17	120.0	C22—C23—H23	119.6
C9—O1—C2—C3	−42.9 (2)	C3—C4—C10—C5	177.17 (19)
C9—O1—C2—C18	84.6 (2)	C4—C3—C11—C12	−179.93 (19)
O1—C2—C3—C11	−141.2 (2)	C2—C3—C11—C12	0.0 (4)
C18—C2—C3—C11	94.6 (2)	C3—C11—C12—C13	−26.0 (3)
O1—C2—C3—C4	38.7 (2)	C3—C11—C12—C17	153.9 (2)
C18—C2—C3—C4	−85.5 (2)	C17—C12—C13—C14	0.0
C11—C3—C4—O4	−10.5 (3)	C11—C12—C13—C14	179.93 (16)
C2—C3—C4—O4	169.6 (2)	C12—C13—C14—C15	0.0
C11—C3—C4—C10	166.58 (19)	C13—C14—C15—C16	0.0
C2—C3—C4—C10	−13.4 (3)	C14—C15—C16—C17	0.0
C10—C5—C6—C7	−1.7 (4)	C15—C16—C17—C12	0.0
C5—C6—C7—C8	2.4 (4)	C13—C12—C17—C16	0.0
C6—C7—C8—C9	−0.3 (3)	C11—C12—C17—C16	−179.93 (15)
C2—O1—C9—C10	21.3 (3)	O1—C2—C18—C23	−123.2 (2)
C2—O1—C9—C8	−162.10 (17)	C3—C2—C18—C23	3.2 (3)
C7—C8—C9—O1	−179.08 (19)	O1—C2—C18—C19	57.6 (2)
C7—C8—C9—C10	−2.4 (3)	C3—C2—C18—C19	−176.08 (17)
O1—C9—C10—C5	179.55 (18)	C23—C18—C19—C20	1.1 (3)
C8—C9—C10—C5	3.1 (3)	C2—C18—C19—C20	−179.64 (17)
O1—C9—C10—C4	6.5 (3)	C18—C19—C20—C21	−0.5 (3)
C8—C9—C10—C4	−170.01 (19)	C19—C20—C21—C22	−0.4 (3)
C6—C5—C10—C9	−1.0 (3)	C20—C21—C22—C23	0.7 (3)
C6—C5—C10—C4	172.0 (2)	C19—C18—C23—C22	−0.7 (3)
O4—C4—C10—C9	167.2 (2)	C2—C18—C23—C22	−180.0 (2)
C3—C4—C10—C9	−9.8 (3)	C21—C22—C23—C18	−0.2 (4)
O4—C4—C10—C5	−5.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O4^i	0.95	2.47	3.353 (3)	154
C17—H17···O4^i	0.95	2.64	3.353 (2)	132
C21—H21···O4^ii	0.95	2.68	3.267 (3)	120

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

(E)-3-(4-Methylbenzylidene)-2-phenylchroman-4-one (compound_II_AAG9)

Crystal data

C23H18O2	F(000) = 688
Mr = 326.37	Dx = 1.263 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.6799 (5) Å	Cell parameters from 4576 reflections
b = 7.9102 (2) Å	θ = 3.2–35.6°
c = 13.1511 (3) Å	µ = 0.08 mm^−1
β = 98.558 (3)°	T = 100 K
V = 1715.85 (8) Å^3	Needle, colorless
Z = 4	0.28 × 0.1 × 0.1 mm

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	3550 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	2927 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.031
Detector resolution: 10.4498 pixels mm^-1	θmax = 26.5°, θmin = 3.1°
ω scans	h = −20→20
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −9→9
Tmin = 0.833, Tmax = 1.000	l = −11→16
13962 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)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.0551P)^2 + 0.3869P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3550 reflections	Δρmax = 0.19 e Å^−3
227 parameters	Δρmin = −0.23 e Å^−3
0 restraints

Special details

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

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

	x	y	z	Uiso*/Ueq
O1	0.13016 (5)	0.69823 (11)	0.61728 (6)	0.0197 (2)
O4	0.24076 (6)	0.72695 (14)	0.91481 (7)	0.0330 (3)
C2	0.21464 (7)	0.64404 (15)	0.63602 (9)	0.0167 (2)
H2	0.2425	0.6974	0.5818	0.020*
C3	0.25695 (7)	0.70595 (14)	0.73857 (9)	0.0169 (2)
C4	0.20880 (8)	0.70299 (15)	0.82561 (9)	0.0199 (3)
C5	0.07131 (8)	0.65060 (17)	0.87504 (10)	0.0249 (3)
H5	0.0945	0.6518	0.9455	0.030*
C6	−0.01103 (8)	0.62868 (19)	0.84830 (11)	0.0304 (3)
H6	−0.0445	0.6141	0.9001	0.036*
C7	−0.04520 (8)	0.6279 (2)	0.74468 (11)	0.0325 (3)
H7	−0.1021	0.6131	0.7265	0.039*
C8	0.00253 (8)	0.64841 (18)	0.66811 (10)	0.0273 (3)
H8	−0.0212	0.6477	0.5978	0.033*
C9	0.08575 (8)	0.67000 (15)	0.69525 (9)	0.0195 (3)
C10	0.12126 (7)	0.67117 (15)	0.79869 (9)	0.0196 (3)
C11	0.33397 (7)	0.76156 (15)	0.75777 (9)	0.0185 (3)
H11	0.3504	0.7991	0.8263	0.022*
C12	0.39695 (7)	0.77435 (15)	0.69160 (9)	0.0192 (3)
C13	0.39774 (7)	0.68092 (16)	0.60070 (9)	0.0210 (3)
H13	0.3545	0.6054	0.5780	0.025*
C14	0.46100 (8)	0.69780 (17)	0.54379 (9)	0.0225 (3)
H14	0.4597	0.6347	0.4821	0.027*
C15	0.52641 (8)	0.80485 (17)	0.57477 (10)	0.0254 (3)
C16	0.52603 (8)	0.89659 (18)	0.66538 (11)	0.0295 (3)
H16	0.5699	0.9705	0.6884	0.035*
C17	0.46310 (8)	0.88198 (17)	0.72228 (10)	0.0253 (3)
H17	0.4646	0.9462	0.7836	0.030*
C18	0.59644 (9)	0.8178 (2)	0.51466 (12)	0.0346 (3)
H18A	0.6390	0.7379	0.5426	0.052*
H18B	0.6182	0.9331	0.5200	0.052*
H18C	0.5776	0.7908	0.4423	0.052*
C21	0.21801 (7)	0.45373 (15)	0.62104 (9)	0.0177 (3)
C22	0.18813 (7)	0.38872 (16)	0.52380 (9)	0.0220 (3)
H22	0.1658	0.4631	0.4702	0.026*
C23	0.19088 (8)	0.21637 (17)	0.50521 (10)	0.0267 (3)
H23	0.1705	0.1731	0.4390	0.032*
C24	0.22339 (8)	0.10705 (17)	0.58321 (11)	0.0284 (3)
H24	0.2254	−0.0109	0.5704	0.034*
C25	0.25287 (8)	0.17031 (17)	0.67978 (11)	0.0285 (3)
H25	0.2749	0.0955	0.7332	0.034*
C26	0.25024 (8)	0.34321 (16)	0.69859 (10)	0.0227 (3)
H26	0.2706	0.3860	0.7649	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0176 (4)	0.0237 (5)	0.0177 (4)	0.0045 (3)	0.0022 (3)	0.0018 (3)
O4	0.0259 (5)	0.0560 (7)	0.0170 (4)	−0.0066 (5)	0.0030 (4)	−0.0072 (4)
C2	0.0152 (6)	0.0182 (6)	0.0167 (5)	0.0011 (4)	0.0023 (4)	0.0012 (4)
C3	0.0197 (6)	0.0134 (6)	0.0174 (6)	0.0020 (4)	0.0022 (5)	0.0006 (4)
C4	0.0219 (6)	0.0207 (6)	0.0173 (6)	0.0009 (5)	0.0029 (5)	−0.0007 (5)
C5	0.0258 (7)	0.0278 (7)	0.0219 (6)	0.0013 (5)	0.0062 (5)	−0.0014 (5)
C6	0.0251 (7)	0.0378 (8)	0.0308 (7)	−0.0009 (6)	0.0126 (6)	−0.0028 (6)
C7	0.0180 (7)	0.0430 (9)	0.0371 (8)	0.0000 (6)	0.0055 (6)	−0.0056 (6)
C8	0.0211 (7)	0.0343 (8)	0.0254 (6)	0.0034 (6)	0.0004 (5)	−0.0019 (6)
C9	0.0202 (6)	0.0177 (6)	0.0211 (6)	0.0029 (5)	0.0047 (5)	−0.0003 (5)
C10	0.0207 (6)	0.0180 (6)	0.0203 (6)	0.0016 (5)	0.0039 (5)	−0.0017 (5)
C11	0.0220 (6)	0.0168 (6)	0.0162 (5)	0.0010 (5)	0.0011 (5)	−0.0011 (4)
C12	0.0174 (6)	0.0197 (6)	0.0199 (6)	0.0023 (5)	0.0011 (5)	0.0018 (5)
C13	0.0184 (6)	0.0213 (6)	0.0224 (6)	0.0005 (5)	0.0004 (5)	−0.0010 (5)
C14	0.0214 (6)	0.0264 (7)	0.0194 (6)	0.0046 (5)	0.0015 (5)	−0.0006 (5)
C15	0.0210 (6)	0.0269 (7)	0.0291 (7)	0.0024 (5)	0.0062 (5)	0.0031 (5)
C16	0.0214 (7)	0.0298 (7)	0.0376 (8)	−0.0074 (5)	0.0051 (6)	−0.0058 (6)
C17	0.0235 (7)	0.0270 (7)	0.0251 (6)	−0.0031 (5)	0.0024 (5)	−0.0068 (5)
C18	0.0244 (7)	0.0407 (9)	0.0413 (8)	−0.0007 (6)	0.0132 (6)	0.0009 (7)
C21	0.0146 (6)	0.0182 (6)	0.0212 (6)	−0.0013 (4)	0.0055 (5)	−0.0009 (5)
C22	0.0201 (6)	0.0230 (7)	0.0229 (6)	−0.0012 (5)	0.0030 (5)	−0.0015 (5)
C23	0.0233 (7)	0.0261 (7)	0.0320 (7)	−0.0058 (5)	0.0080 (5)	−0.0094 (5)
C24	0.0249 (7)	0.0166 (6)	0.0459 (8)	−0.0014 (5)	0.0132 (6)	−0.0038 (6)
C25	0.0272 (7)	0.0211 (7)	0.0376 (8)	0.0036 (5)	0.0066 (6)	0.0062 (6)
C26	0.0222 (6)	0.0215 (6)	0.0243 (6)	0.0012 (5)	0.0038 (5)	0.0020 (5)

Geometric parameters (Å, º)

O1—C9	1.3696 (14)	C13—C14	1.3879 (17)
O1—C2	1.4582 (14)	C13—H13	0.9500
O4—C4	1.2288 (15)	C14—C15	1.3933 (19)
C2—C3	1.5078 (16)	C14—H14	0.9500
C2—C21	1.5204 (16)	C15—C16	1.3960 (19)
C2—H2	1.0000	C15—C18	1.5082 (18)
C3—C11	1.3458 (17)	C16—C17	1.3817 (19)
C3—C4	1.4932 (16)	C16—H16	0.9500
C4—C10	1.4720 (17)	C17—H17	0.9500
C5—C6	1.3770 (19)	C18—H18A	0.9800
C5—C10	1.4064 (17)	C18—H18B	0.9800
C5—H5	0.9500	C18—H18C	0.9800
C6—C7	1.397 (2)	C21—C26	1.3893 (17)
C6—H6	0.9500	C21—C22	1.3995 (17)
C7—C8	1.3830 (19)	C22—C23	1.3870 (18)
C7—H7	0.9500	C22—H22	0.9500
C8—C9	1.3915 (18)	C23—C24	1.389 (2)
C8—H8	0.9500	C23—H23	0.9500
C9—C10	1.4006 (17)	C24—C25	1.385 (2)
C11—C12	1.4637 (17)	C24—H24	0.9500
C11—H11	0.9500	C25—C26	1.3917 (19)
C12—C17	1.4046 (17)	C25—H25	0.9500
C12—C13	1.4072 (17)	C26—H26	0.9500
C9—O1—C2	116.24 (9)	C14—C13—H13	119.6
O1—C2—C3	111.57 (9)	C12—C13—H13	119.6
O1—C2—C21	108.82 (9)	C13—C14—C15	121.73 (12)
C3—C2—C21	114.59 (10)	C13—C14—H14	119.1
O1—C2—H2	107.2	C15—C14—H14	119.1
C3—C2—H2	107.2	C14—C15—C16	117.56 (12)
C21—C2—H2	107.2	C14—C15—C18	121.46 (12)
C11—C3—C4	117.95 (10)	C16—C15—C18	120.96 (13)
C11—C3—C2	125.50 (11)	C17—C16—C15	121.27 (12)
C4—C3—C2	116.55 (10)	C17—C16—H16	119.4
O4—C4—C10	122.00 (11)	C15—C16—H16	119.4
O4—C4—C3	121.53 (11)	C16—C17—C12	121.52 (12)
C10—C4—C3	116.47 (10)	C16—C17—H17	119.2
C6—C5—C10	120.44 (12)	C12—C17—H17	119.2
C6—C5—H5	119.8	C15—C18—H18A	109.5
C10—C5—H5	119.8	C15—C18—H18B	109.5
C5—C6—C7	119.76 (12)	H18A—C18—H18B	109.5
C5—C6—H6	120.1	C15—C18—H18C	109.5
C7—C6—H6	120.1	H18A—C18—H18C	109.5
C8—C7—C6	120.96 (13)	H18B—C18—H18C	109.5
C8—C7—H7	119.5	C26—C21—C22	119.07 (12)
C6—C7—H7	119.5	C26—C21—C2	123.07 (11)
C7—C8—C9	119.21 (12)	C22—C21—C2	117.85 (11)
C7—C8—H8	120.4	C23—C22—C21	120.37 (12)
C9—C8—H8	120.4	C23—C22—H22	119.8
O1—C9—C8	117.26 (11)	C21—C22—H22	119.8
O1—C9—C10	121.89 (11)	C22—C23—C24	120.09 (12)
C8—C9—C10	120.77 (11)	C22—C23—H23	120.0
C9—C10—C5	118.87 (12)	C24—C23—H23	120.0
C9—C10—C4	119.72 (11)	C25—C24—C23	119.90 (12)
C5—C10—C4	121.33 (11)	C25—C24—H24	120.0
C3—C11—C12	131.34 (11)	C23—C24—H24	120.0
C3—C11—H11	114.3	C24—C25—C26	120.11 (13)
C12—C11—H11	114.3	C24—C25—H25	119.9
C17—C12—C13	117.13 (11)	C26—C25—H25	119.9
C17—C12—C11	118.27 (11)	C21—C26—C25	120.45 (12)
C13—C12—C11	124.55 (11)	C21—C26—H26	119.8
C14—C13—C12	120.78 (12)	C25—C26—H26	119.8

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4^i	1.00	2.27	3.1737 (14)	149
C5—H5···O1^ii	0.95	2.54	3.4076 (15)	152
C24—H24···O4^iii	0.95	2.71	3.4871 (17)	140

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

(E)-3-(3-Methylbenzylidene)-2-phenylchroman-4-one (compound_III_AAG1)

Crystal data

C23H18O2	Z = 2
Mr = 326.37	F(000) = 344
Triclinic, P1	Dx = 1.275 Mg m^−3
a = 8.9094 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.6578 (3) Å	Cell parameters from 3948 reflections
c = 10.9044 (4) Å	θ = 3.5–36.1°
α = 104.378 (3)°	µ = 0.08 mm^−1
β = 109.425 (3)°	T = 100 K
γ = 91.902 (3)°	Needle, colorless
V = 850.24 (5) Å^3	0.28 × 0.1 × 0.08 mm

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	3509 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	2999 reflections with I > 2σ(I)
Detector resolution: 10.4498 pixels mm^-1	Rint = 0.021
ω scans	θmax = 26.5°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −11→11
Tmin = 0.736, Tmax = 1.000	k = −12→12
7284 measured reflections	l = −13→10

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.0439P)^2 + 0.2079P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
3509 reflections	Δρmax = 0.24 e Å^−3
227 parameters	Δρmin = −0.21 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
O1	0.57118 (10)	0.44640 (9)	0.37188 (8)	0.0200 (2)
O4	0.38766 (10)	0.03505 (9)	0.32719 (8)	0.0229 (2)
C21	0.66313 (13)	0.29543 (13)	0.20350 (11)	0.0170 (2)
C12	0.89045 (14)	0.16807 (12)	0.54388 (12)	0.0192 (3)
C2	0.66990 (14)	0.33222 (12)	0.35024 (11)	0.0172 (2)
H2	0.7834	0.3701	0.4101	0.021*
C3	0.61964 (14)	0.20436 (12)	0.39022 (11)	0.0176 (2)
C11	0.71562 (14)	0.13781 (13)	0.47467 (11)	0.0188 (3)
H11	0.6638	0.0611	0.4920	0.023*
C9	0.40917 (14)	0.40489 (13)	0.31451 (11)	0.0188 (3)
C4	0.44417 (14)	0.15501 (13)	0.33244 (11)	0.0179 (2)
C26	0.66779 (14)	0.15547 (13)	0.13257 (12)	0.0204 (3)
H26	0.6718	0.0796	0.1744	0.024*
C10	0.34138 (14)	0.26263 (13)	0.28726 (11)	0.0188 (3)
C13	0.99590 (15)	0.20421 (13)	0.48267 (12)	0.0221 (3)
H13	0.9549	0.2119	0.3926	0.026*
C17	0.95460 (15)	0.15826 (13)	0.67717 (12)	0.0203 (3)
H17	0.8844	0.1306	0.7185	0.024*
C16	1.11883 (15)	0.18806 (13)	0.75045 (12)	0.0215 (3)
C5	0.17385 (15)	0.22886 (14)	0.22882 (12)	0.0228 (3)
H5	0.1266	0.1325	0.2086	0.027*
C22	0.65751 (14)	0.40519 (13)	0.14018 (12)	0.0208 (3)
H22	0.6544	0.5013	0.1876	0.025*
C25	0.66659 (15)	0.12572 (14)	0.00015 (12)	0.0230 (3)
H25	0.6695	0.0297	−0.0476	0.028*
C24	0.66114 (14)	0.23528 (14)	−0.06185 (12)	0.0221 (3)
H24	0.6607	0.2149	−0.1518	0.027*
C14	1.16003 (15)	0.22879 (14)	0.55301 (13)	0.0249 (3)
H14	1.2311	0.2514	0.5103	0.030*
C15	1.22082 (15)	0.22054 (13)	0.68555 (12)	0.0234 (3)
H15	1.3335	0.2373	0.7327	0.028*
C23	0.65634 (15)	0.37523 (14)	0.00852 (12)	0.0232 (3)
H23	0.6522	0.4508	−0.0336	0.028*
C8	0.31165 (16)	0.51168 (14)	0.28802 (12)	0.0243 (3)
H8	0.3579	0.6084	0.3085	0.029*
C6	0.07720 (15)	0.33358 (16)	0.20038 (13)	0.0274 (3)
H6	−0.0359	0.3095	0.1599	0.033*
C7	0.14682 (16)	0.47552 (15)	0.23157 (13)	0.0279 (3)
H7	0.0801	0.5482	0.2138	0.033*
C18	1.18325 (16)	0.18957 (15)	0.89766 (12)	0.0283 (3)
H18A	1.1300	0.1062	0.9099	0.042*
H18B	1.1624	0.2785	0.9527	0.042*
H18C	1.2991	0.1850	0.9259	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0226 (4)	0.0158 (4)	0.0191 (4)	0.0016 (3)	0.0072 (3)	0.0009 (3)
O4	0.0240 (4)	0.0210 (5)	0.0226 (4)	−0.0023 (3)	0.0066 (4)	0.0069 (4)
C21	0.0138 (5)	0.0185 (6)	0.0176 (5)	0.0001 (4)	0.0045 (4)	0.0046 (5)
C12	0.0228 (6)	0.0134 (6)	0.0191 (6)	0.0031 (4)	0.0056 (5)	0.0028 (4)
C2	0.0176 (5)	0.0157 (6)	0.0168 (5)	0.0013 (4)	0.0051 (4)	0.0031 (4)
C3	0.0212 (6)	0.0166 (6)	0.0141 (5)	0.0012 (4)	0.0071 (4)	0.0014 (4)
C11	0.0230 (6)	0.0162 (6)	0.0167 (5)	0.0001 (5)	0.0083 (5)	0.0022 (4)
C9	0.0222 (6)	0.0217 (6)	0.0121 (5)	0.0032 (5)	0.0072 (4)	0.0025 (5)
C4	0.0225 (6)	0.0191 (6)	0.0123 (5)	0.0004 (5)	0.0078 (4)	0.0027 (4)
C26	0.0240 (6)	0.0176 (6)	0.0191 (6)	0.0009 (5)	0.0068 (5)	0.0056 (5)
C10	0.0214 (6)	0.0221 (6)	0.0138 (5)	0.0032 (5)	0.0079 (4)	0.0043 (5)
C13	0.0244 (6)	0.0227 (7)	0.0180 (6)	0.0027 (5)	0.0068 (5)	0.0048 (5)
C17	0.0252 (6)	0.0155 (6)	0.0211 (6)	0.0038 (5)	0.0088 (5)	0.0055 (5)
C16	0.0286 (7)	0.0141 (6)	0.0181 (6)	0.0043 (5)	0.0050 (5)	0.0026 (5)
C5	0.0224 (6)	0.0290 (7)	0.0182 (6)	0.0013 (5)	0.0086 (5)	0.0067 (5)
C22	0.0219 (6)	0.0169 (6)	0.0245 (6)	0.0032 (5)	0.0091 (5)	0.0057 (5)
C25	0.0268 (6)	0.0195 (6)	0.0200 (6)	0.0015 (5)	0.0076 (5)	0.0019 (5)
C24	0.0212 (6)	0.0289 (7)	0.0167 (5)	0.0035 (5)	0.0062 (5)	0.0075 (5)
C14	0.0251 (6)	0.0256 (7)	0.0241 (6)	0.0016 (5)	0.0105 (5)	0.0044 (5)
C15	0.0204 (6)	0.0200 (6)	0.0242 (6)	0.0017 (5)	0.0037 (5)	0.0019 (5)
C23	0.0243 (6)	0.0247 (7)	0.0250 (6)	0.0052 (5)	0.0099 (5)	0.0127 (5)
C8	0.0328 (7)	0.0217 (7)	0.0194 (6)	0.0075 (5)	0.0111 (5)	0.0043 (5)
C6	0.0206 (6)	0.0400 (8)	0.0231 (6)	0.0072 (5)	0.0085 (5)	0.0098 (6)
C7	0.0301 (7)	0.0331 (8)	0.0238 (6)	0.0156 (6)	0.0115 (5)	0.0096 (6)
C18	0.0315 (7)	0.0295 (7)	0.0205 (6)	0.0051 (5)	0.0045 (5)	0.0073 (5)

Geometric parameters (Å, º)

O1—C9	1.3682 (14)	C17—H17	0.9500
O1—C2	1.4555 (14)	C16—C15	1.3942 (18)
O4—C4	1.2281 (14)	C16—C18	1.5105 (16)
C21—C26	1.3903 (17)	C5—C6	1.3771 (19)
C21—C22	1.3953 (17)	C5—H5	0.9500
C21—C2	1.5305 (15)	C22—C23	1.3887 (17)
C12—C13	1.4004 (17)	C22—H22	0.9500
C12—C17	1.4027 (16)	C25—C24	1.3841 (18)
C12—C11	1.4695 (16)	C25—H25	0.9500
C2—C3	1.5086 (16)	C24—C23	1.3885 (18)
C2—H2	1.0000	C24—H24	0.9500
C3—C11	1.3413 (17)	C14—C15	1.3885 (18)
C3—C4	1.4881 (15)	C14—H14	0.9500
C11—H11	0.9500	C15—H15	0.9500
C9—C8	1.3938 (17)	C23—H23	0.9500
C9—C10	1.4012 (17)	C8—C7	1.3839 (18)
C4—C10	1.4762 (17)	C8—H8	0.9500
C26—C25	1.3969 (16)	C6—C7	1.397 (2)
C26—H26	0.9500	C6—H6	0.9500
C10—C5	1.4043 (16)	C7—H7	0.9500
C13—C14	1.3868 (17)	C18—H18A	0.9800
C13—H13	0.9500	C18—H18B	0.9800
C17—C16	1.3937 (17)	C18—H18C	0.9800
C9—O1—C2	115.14 (9)	C17—C16—C18	120.52 (11)
C26—C21—C22	118.86 (11)	C15—C16—C18	121.13 (11)
C26—C21—C2	121.58 (10)	C6—C5—C10	120.87 (12)
C22—C21—C2	119.53 (11)	C6—C5—H5	119.6
C13—C12—C17	118.55 (11)	C10—C5—H5	119.6
C13—C12—C11	123.22 (10)	C23—C22—C21	120.62 (12)
C17—C12—C11	118.22 (11)	C23—C22—H22	119.7
O1—C2—C3	110.50 (9)	C21—C22—H22	119.7
O1—C2—C21	109.10 (9)	C24—C25—C26	120.39 (12)
C3—C2—C21	113.52 (9)	C24—C25—H25	119.8
O1—C2—H2	107.8	C26—C25—H25	119.8
C3—C2—H2	107.8	C25—C24—C23	119.46 (11)
C21—C2—H2	107.8	C25—C24—H24	120.3
C11—C3—C4	118.88 (10)	C23—C24—H24	120.3
C11—C3—C2	126.48 (11)	C13—C14—C15	120.26 (12)
C4—C3—C2	114.58 (10)	C13—C14—H14	119.9
C3—C11—C12	128.46 (11)	C15—C14—H14	119.9
C3—C11—H11	115.8	C14—C15—C16	120.92 (11)
C12—C11—H11	115.8	C14—C15—H15	119.5
O1—C9—C8	117.18 (11)	C16—C15—H15	119.5
O1—C9—C10	122.27 (11)	C24—C23—C22	120.31 (11)
C8—C9—C10	120.51 (11)	C24—C23—H23	119.8
O4—C4—C10	121.96 (11)	C22—C23—H23	119.8
O4—C4—C3	122.58 (11)	C7—C8—C9	119.42 (12)
C10—C4—C3	115.40 (10)	C7—C8—H8	120.3
C21—C26—C25	120.37 (11)	C9—C8—H8	120.3
C21—C26—H26	119.8	C5—C6—C7	119.48 (12)
C25—C26—H26	119.8	C5—C6—H6	120.3
C9—C10—C5	118.78 (11)	C7—C6—H6	120.3
C9—C10—C4	119.87 (11)	C8—C7—C6	120.90 (12)
C5—C10—C4	121.05 (11)	C8—C7—H7	119.5
C14—C13—C12	120.24 (11)	C6—C7—H7	119.5
C14—C13—H13	119.9	C16—C18—H18A	109.5
C12—C13—H13	119.9	C16—C18—H18B	109.5
C16—C17—C12	121.63 (11)	H18A—C18—H18B	109.5
C16—C17—H17	119.2	C16—C18—H18C	109.5
C12—C17—H17	119.2	H18A—C18—H18C	109.5
C17—C16—C15	118.32 (11)	H18B—C18—H18C	109.5
C9—O1—C2—C3	−51.97 (12)	C3—C4—C10—C9	−7.36 (15)
C9—O1—C2—C21	73.51 (11)	O4—C4—C10—C5	−3.72 (17)
C26—C21—C2—O1	−145.49 (10)	C3—C4—C10—C5	178.94 (10)
C22—C21—C2—O1	36.67 (14)	C17—C12—C13—C14	0.34 (18)
C26—C21—C2—C3	−21.79 (15)	C11—C12—C13—C14	−178.77 (12)
C22—C21—C2—C3	160.38 (10)	C13—C12—C17—C16	2.12 (18)
O1—C2—C3—C11	−127.71 (12)	C11—C12—C17—C16	−178.73 (11)
C21—C2—C3—C11	109.35 (13)	C12—C17—C16—C15	−3.55 (18)
O1—C2—C3—C4	49.49 (12)	C12—C17—C16—C18	174.54 (12)
C21—C2—C3—C4	−73.45 (13)	C9—C10—C5—C6	−0.92 (17)
C4—C3—C11—C12	−179.62 (11)	C4—C10—C5—C6	172.84 (11)
C2—C3—C11—C12	−2.5 (2)	C26—C21—C22—C23	0.09 (17)
C13—C12—C11—C3	−39.46 (19)	C2—C21—C22—C23	177.99 (11)
C17—C12—C11—C3	141.43 (13)	C21—C26—C25—C24	0.16 (18)
C2—O1—C9—C8	−157.01 (10)	C26—C25—C24—C23	−0.21 (18)
C2—O1—C9—C10	25.25 (14)	C12—C13—C14—C15	−1.3 (2)
C11—C3—C4—O4	−20.52 (17)	C13—C14—C15—C16	−0.2 (2)
C2—C3—C4—O4	162.05 (11)	C17—C16—C15—C14	2.57 (19)
C11—C3—C4—C10	156.80 (11)	C18—C16—C15—C14	−175.51 (12)
C2—C3—C4—C10	−20.63 (14)	C25—C24—C23—C22	0.20 (18)
C22—C21—C26—C25	−0.10 (17)	C21—C22—C23—C24	−0.15 (18)
C2—C21—C26—C25	−177.95 (11)	O1—C9—C8—C7	−179.21 (10)
O1—C9—C10—C5	179.68 (10)	C10—C9—C8—C7	−1.43 (17)
C8—C9—C10—C5	2.01 (17)	C10—C5—C6—C7	−0.74 (18)
O1—C9—C10—C4	5.84 (16)	C9—C8—C7—C6	−0.26 (18)
C8—C9—C10—C4	−171.83 (10)	C5—C6—C7—C8	1.35 (19)
O4—C4—C10—C9	169.98 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O4^i	0.95	2.54	3.3635 (14)	145
C17—H17···O4^i	0.95	2.69	3.5025 (15)	144
C24—H24···O4^ii	0.95	2.60	3.2731 (15)	128

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

(E)-3-(4-Methoxybenzylidene)-2-phenylchroman-4-one (compound_IV_AAG2)

Crystal data

C23H18O3	F(000) = 2160
Mr = 342.37	Dx = 1.306 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 23.4111 (3) Å	Cell parameters from 7810 reflections
b = 8.0027 (1) Å	θ = 2.6–74.1°
c = 28.1094 (5) Å	µ = 0.69 mm^−1
β = 97.156 (1)°	T = 100 K
V = 5225.33 (13) Å^3	Needle, colorless
Z = 12	0.28 × 0.1 × 0.08 mm

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	7742 reflections with I > 2σ(I)
ω scans	Rint = 0.022
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	θmax = 67.5°, θmin = 2.3°
Tmin = 0.997, Tmax = 1.000	h = −26→28
15971 measured reflections	k = −9→7
9323 independent reflections	l = −33→30

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0515P)^2 + 0.9818P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
9323 reflections	Δρmax = 0.20 e Å^−3
706 parameters	Δρmin = −0.21 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
O1	0.10459 (3)	0.83638 (11)	0.53474 (3)	0.01769 (18)
O4	0.26145 (4)	0.77397 (13)	0.48650 (3)	0.0270 (2)
O3	0.31526 (4)	0.78657 (13)	0.78489 (3)	0.0293 (2)
C5	0.16094 (5)	0.81050 (15)	0.46836 (4)	0.0195 (3)
C4	0.21516 (5)	0.80412 (15)	0.50102 (4)	0.0190 (3)
C6	0.16063 (6)	0.79075 (18)	0.41871 (5)	0.0248 (3)
H6	0.1960	0.7805	0.4057	0.030*
C3	0.21023 (5)	0.83055 (14)	0.55297 (4)	0.0171 (2)
C17	0.25594 (5)	0.78916 (15)	0.58462 (5)	0.0186 (2)
H17	0.2877	0.7476	0.5702	0.022*
C21	0.29676 (6)	0.79508 (16)	0.73726 (5)	0.0221 (3)
C9	0.05653 (6)	0.82182 (18)	0.45664 (5)	0.0253 (3)
H9	0.0210	0.8326	0.4694	0.030*
C19	0.23508 (5)	0.88924 (15)	0.66704 (4)	0.0187 (2)
H19	0.2033	0.9545	0.6534	0.022*
C23	0.31335 (5)	0.70289 (17)	0.65885 (5)	0.0229 (3)
H23	0.3355	0.6391	0.6393	0.028*
C18	0.26619 (5)	0.79578 (15)	0.63689 (5)	0.0192 (3)
C16	0.10377 (5)	1.16182 (16)	0.58418 (5)	0.0214 (3)
H16	0.0767	1.0927	0.5973	0.026*
C2	0.15441 (5)	0.89981 (15)	0.56591 (4)	0.0162 (2)
H2	0.1505	0.8617	0.5992	0.019*
C14	0.13611 (6)	1.43522 (16)	0.56434 (5)	0.0252 (3)
H14	0.1310	1.5530	0.5636	0.030*
C15	0.09655 (6)	1.33437 (17)	0.58351 (5)	0.0251 (3)
H15	0.0646	1.3830	0.5961	0.030*
C10	0.10837 (5)	0.82584 (15)	0.48687 (4)	0.0184 (2)
C11	0.15050 (5)	1.08964 (15)	0.56562 (4)	0.0173 (2)
C12	0.19031 (5)	1.19147 (16)	0.54688 (4)	0.0194 (3)
H12	0.2224	1.1431	0.5345	0.023*
C20	0.24966 (5)	0.88868 (16)	0.71658 (5)	0.0202 (3)
H20	0.2276	0.9519	0.7363	0.024*
C13	0.18315 (6)	1.36457 (17)	0.54629 (5)	0.0236 (3)
H13	0.2104	1.4341	0.5336	0.028*
C8	0.05741 (6)	0.8019 (2)	0.40788 (5)	0.0317 (3)
H8	0.0222	0.7989	0.3871	0.038*
C22	0.32840 (6)	0.70158 (17)	0.70782 (5)	0.0251 (3)
H22	0.3603	0.6370	0.7215	0.030*
C7	0.10937 (6)	0.7862 (2)	0.38870 (5)	0.0307 (3)
H7	0.1094	0.7724	0.3551	0.037*
C211	0.28785 (6)	0.8935 (2)	0.81596 (5)	0.0321 (3)
H21A	0.2464	0.8712	0.8119	0.048*
H21B	0.2946	1.0105	0.8080	0.048*
H21C	0.3038	0.8721	0.8493	0.048*
O31	0.56062 (3)	0.27594 (11)	0.79683 (3)	0.01768 (18)
O34	0.40526 (4)	0.20680 (13)	0.84703 (3)	0.0264 (2)
C40	0.55790 (5)	0.26249 (15)	0.84483 (4)	0.0185 (2)
O33	0.34425 (4)	0.32326 (14)	0.55019 (3)	0.0311 (2)
C41	0.51536 (5)	0.53223 (15)	0.76805 (4)	0.0174 (2)
C42	0.47572 (6)	0.63647 (16)	0.78610 (4)	0.0209 (3)
H42	0.4431	0.5901	0.7983	0.025*
C33	0.45460 (5)	0.27542 (15)	0.78040 (4)	0.0175 (2)
C46	0.56266 (6)	0.60212 (17)	0.74971 (5)	0.0228 (3)
H46	0.5895	0.5315	0.7369	0.027*
C48	0.39692 (5)	0.26975 (16)	0.69692 (5)	0.0194 (3)
C36	0.50724 (6)	0.22330 (17)	0.91374 (5)	0.0244 (3)
H36	0.4722	0.2119	0.9272	0.029*
C47	0.40779 (5)	0.24452 (15)	0.74877 (5)	0.0192 (3)
H47	0.3763	0.1982	0.7625	0.023*
C52	0.33472 (6)	0.19928 (18)	0.62375 (5)	0.0274 (3)
H52	0.3035	0.1363	0.6081	0.033*
C35	0.50597 (5)	0.24518 (15)	0.86402 (5)	0.0196 (3)
C43	0.48379 (6)	0.80906 (17)	0.78637 (5)	0.0267 (3)
H43	0.4567	0.8801	0.7987	0.032*
C34	0.45110 (5)	0.24053 (15)	0.83209 (5)	0.0191 (3)
C45	0.57070 (6)	0.77351 (18)	0.75011 (5)	0.0279 (3)
H45	0.6031	0.8203	0.7377	0.034*
C37	0.55895 (6)	0.2183 (2)	0.94308 (5)	0.0305 (3)
H37	0.5596	0.2035	0.9767	0.037*
C51	0.36454 (6)	0.31041 (17)	0.59743 (5)	0.0223 (3)
C50	0.41129 (5)	0.39894 (16)	0.62069 (5)	0.0200 (3)
H50	0.4324	0.4729	0.6031	0.024*
C44	0.53120 (7)	0.87706 (17)	0.76868 (5)	0.0292 (3)
H44	0.5368	0.9947	0.7692	0.035*
C49	0.42686 (5)	0.37853 (16)	0.66989 (4)	0.0195 (3)
H49	0.4586	0.4400	0.6854	0.023*
C39	0.61035 (6)	0.25690 (18)	0.87438 (5)	0.0252 (3)
H39	0.6456	0.2681	0.8611	0.030*
C32	0.51044 (5)	0.34316 (15)	0.76700 (4)	0.0166 (2)
H32	0.5133	0.3069	0.7333	0.020*
C53	0.35057 (6)	0.18097 (17)	0.67222 (5)	0.0248 (3)
H53	0.3295	0.1059	0.6896	0.030*
C38	0.61048 (6)	0.2350 (2)	0.92305 (5)	0.0310 (3)
H38	0.6461	0.2311	0.9433	0.037*
C511	0.36840 (6)	0.4486 (2)	0.52261 (5)	0.0298 (3)
H51A	0.4095	0.4262	0.5222	0.045*
H51B	0.3636	0.5585	0.5370	0.045*
H51C	0.3487	0.4473	0.4897	0.045*
O61	0.22635 (4)	0.40047 (11)	0.13133 (3)	0.01906 (19)
O64	0.07332 (4)	0.32928 (14)	0.18334 (3)	0.0316 (2)
O63	0.01585 (4)	0.29424 (13)	−0.11462 (3)	0.0294 (2)
C63	0.12093 (5)	0.39015 (15)	0.11531 (4)	0.0186 (3)
C70	0.22422 (5)	0.40593 (15)	0.17964 (5)	0.0193 (3)
C62	0.17574 (5)	0.46126 (15)	0.10066 (4)	0.0175 (2)
H62	0.1788	0.4219	0.0673	0.021*
C76	0.13695 (5)	0.75279 (16)	0.11604 (5)	0.0208 (3)
H76	0.1035	0.7045	0.1263	0.025*
C77	0.07469 (5)	0.34220 (15)	0.08504 (5)	0.0199 (3)
H77	0.0438	0.3011	0.1006	0.024*
C64	0.11821 (5)	0.36726 (16)	0.16759 (5)	0.0207 (3)
C66	0.17394 (6)	0.38554 (17)	0.24932 (5)	0.0242 (3)
H66	0.1391	0.3727	0.2631	0.029*
C75	0.14402 (6)	0.92594 (17)	0.11667 (5)	0.0242 (3)
H75	0.1153	0.9953	0.1275	0.029*
C65	0.17270 (5)	0.38931 (15)	0.19937 (5)	0.0196 (3)
C74	0.19253 (6)	0.99728 (16)	0.10159 (5)	0.0245 (3)
H74	0.1972	1.1152	0.1023	0.029*
C73	0.23435 (6)	0.89628 (17)	0.08536 (5)	0.0237 (3)
H73	0.2676	0.9450	0.0748	0.028*
C78	0.06315 (5)	0.34154 (16)	0.03287 (5)	0.0201 (3)
C71	0.17897 (5)	0.65101 (15)	0.10037 (4)	0.0179 (2)
C69	0.27641 (6)	0.41947 (19)	0.20914 (5)	0.0278 (3)
H69	0.3115	0.4303	0.1956	0.033*
C83	0.01889 (6)	0.23595 (17)	0.01259 (5)	0.0243 (3)
H83	−0.0016	0.1715	0.0333	0.029*
C79	0.09117 (6)	0.43776 (16)	0.00123 (5)	0.0226 (3)
H79	0.1207	0.5129	0.0137	0.027*
C72	0.22748 (5)	0.72430 (16)	0.08461 (5)	0.0208 (3)
H72	0.2560	0.6555	0.0733	0.025*
C82	0.00403 (6)	0.22232 (18)	−0.03621 (5)	0.0261 (3)
H82	−0.0259	0.1487	−0.0488	0.031*
C80	0.07665 (6)	0.42563 (17)	−0.04811 (5)	0.0239 (3)
H80	0.0964	0.4915	−0.0689	0.029*
C68	0.27653 (6)	0.4169 (2)	0.25813 (5)	0.0343 (3)
H68	0.3120	0.4266	0.2784	0.041*
C811	0.04246 (6)	0.3967 (2)	−0.14750 (5)	0.0337 (3)
H81A	0.0339	0.5144	−0.1420	0.051*
H81B	0.0275	0.3661	−0.1805	0.051*
H81C	0.0842	0.3794	−0.1425	0.051*
C67	0.22546 (6)	0.4003 (2)	0.27861 (5)	0.0314 (3)
H67	0.2262	0.3993	0.3125	0.038*
C81	0.03315 (6)	0.31704 (17)	−0.06707 (5)	0.0228 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0148 (4)	0.0201 (4)	0.0181 (4)	−0.0028 (3)	0.0019 (3)	−0.0018 (3)
O4	0.0196 (5)	0.0398 (6)	0.0227 (5)	0.0045 (4)	0.0063 (4)	0.0012 (4)
O3	0.0321 (5)	0.0350 (5)	0.0194 (5)	0.0056 (4)	−0.0023 (4)	0.0010 (4)
C5	0.0205 (6)	0.0170 (6)	0.0211 (6)	−0.0014 (5)	0.0033 (5)	0.0018 (5)
C4	0.0195 (6)	0.0168 (6)	0.0212 (6)	−0.0001 (5)	0.0048 (5)	0.0024 (5)
C6	0.0235 (7)	0.0295 (7)	0.0221 (7)	−0.0030 (5)	0.0051 (5)	0.0015 (5)
C3	0.0180 (6)	0.0133 (5)	0.0202 (6)	−0.0011 (5)	0.0034 (5)	0.0006 (5)
C17	0.0172 (6)	0.0157 (6)	0.0233 (6)	0.0006 (5)	0.0044 (5)	−0.0010 (5)
C21	0.0230 (6)	0.0228 (6)	0.0194 (6)	−0.0039 (5)	−0.0017 (5)	0.0007 (5)
C9	0.0177 (6)	0.0333 (7)	0.0248 (7)	−0.0030 (5)	0.0024 (5)	0.0004 (6)
C19	0.0160 (6)	0.0176 (6)	0.0220 (6)	−0.0002 (5)	0.0005 (5)	0.0008 (5)
C23	0.0195 (6)	0.0241 (6)	0.0246 (7)	0.0034 (5)	0.0005 (5)	−0.0023 (5)
C18	0.0165 (6)	0.0175 (6)	0.0232 (6)	−0.0020 (5)	0.0008 (5)	0.0004 (5)
C16	0.0197 (6)	0.0207 (6)	0.0238 (6)	−0.0002 (5)	0.0029 (5)	−0.0011 (5)
C2	0.0148 (6)	0.0172 (6)	0.0160 (6)	−0.0009 (5)	−0.0002 (4)	−0.0001 (4)
C14	0.0316 (7)	0.0158 (6)	0.0265 (7)	0.0016 (5)	−0.0029 (5)	−0.0006 (5)
C15	0.0235 (7)	0.0224 (7)	0.0290 (7)	0.0047 (5)	0.0012 (5)	−0.0035 (5)
C10	0.0217 (6)	0.0161 (6)	0.0178 (6)	−0.0021 (5)	0.0035 (5)	0.0015 (5)
C11	0.0176 (6)	0.0180 (6)	0.0153 (6)	0.0010 (5)	−0.0016 (4)	0.0001 (5)
C12	0.0201 (6)	0.0197 (6)	0.0180 (6)	−0.0013 (5)	0.0009 (5)	−0.0004 (5)
C20	0.0193 (6)	0.0198 (6)	0.0217 (6)	−0.0024 (5)	0.0032 (5)	−0.0008 (5)
C13	0.0285 (7)	0.0195 (6)	0.0221 (6)	−0.0040 (5)	0.0005 (5)	0.0023 (5)
C8	0.0233 (7)	0.0474 (9)	0.0232 (7)	−0.0053 (6)	−0.0024 (5)	0.0018 (6)
C22	0.0219 (6)	0.0256 (7)	0.0266 (7)	0.0052 (5)	−0.0023 (5)	0.0013 (5)
C7	0.0299 (7)	0.0441 (8)	0.0177 (6)	−0.0063 (6)	0.0013 (5)	0.0012 (6)
C211	0.0318 (7)	0.0444 (9)	0.0197 (7)	0.0020 (7)	0.0012 (5)	−0.0018 (6)
O31	0.0153 (4)	0.0193 (4)	0.0186 (4)	0.0028 (3)	0.0028 (3)	0.0012 (3)
O34	0.0194 (5)	0.0377 (5)	0.0231 (5)	−0.0037 (4)	0.0069 (4)	0.0002 (4)
C40	0.0219 (6)	0.0154 (6)	0.0185 (6)	0.0019 (5)	0.0035 (5)	−0.0017 (5)
O33	0.0304 (5)	0.0389 (6)	0.0217 (5)	−0.0076 (4)	−0.0052 (4)	0.0028 (4)
C41	0.0184 (6)	0.0182 (6)	0.0147 (5)	−0.0008 (5)	−0.0018 (4)	−0.0005 (5)
C42	0.0234 (6)	0.0201 (6)	0.0184 (6)	0.0018 (5)	−0.0002 (5)	−0.0004 (5)
C33	0.0181 (6)	0.0141 (5)	0.0206 (6)	0.0010 (5)	0.0043 (5)	−0.0014 (5)
C46	0.0210 (6)	0.0219 (6)	0.0251 (6)	−0.0016 (5)	0.0013 (5)	0.0010 (5)
C48	0.0162 (6)	0.0197 (6)	0.0222 (6)	0.0006 (5)	0.0020 (5)	−0.0019 (5)
C36	0.0236 (7)	0.0304 (7)	0.0201 (6)	0.0027 (5)	0.0059 (5)	−0.0010 (5)
C47	0.0180 (6)	0.0168 (6)	0.0235 (6)	−0.0008 (5)	0.0050 (5)	−0.0006 (5)
C52	0.0226 (6)	0.0297 (7)	0.0283 (7)	−0.0068 (6)	−0.0029 (5)	−0.0007 (6)
C35	0.0201 (6)	0.0176 (6)	0.0214 (6)	0.0006 (5)	0.0038 (5)	−0.0014 (5)
C43	0.0361 (8)	0.0201 (6)	0.0227 (7)	0.0062 (6)	−0.0013 (5)	−0.0021 (5)
C34	0.0195 (6)	0.0165 (6)	0.0219 (6)	0.0004 (5)	0.0049 (5)	−0.0029 (5)
C45	0.0283 (7)	0.0238 (7)	0.0303 (7)	−0.0072 (6)	−0.0014 (5)	0.0051 (6)
C37	0.0293 (7)	0.0443 (9)	0.0177 (6)	0.0058 (6)	0.0022 (5)	−0.0009 (6)
C51	0.0211 (6)	0.0243 (6)	0.0206 (6)	0.0031 (5)	−0.0010 (5)	−0.0014 (5)
C50	0.0183 (6)	0.0192 (6)	0.0227 (6)	0.0018 (5)	0.0034 (5)	0.0006 (5)
C44	0.0411 (8)	0.0171 (6)	0.0266 (7)	−0.0035 (6)	−0.0065 (6)	0.0005 (5)
C49	0.0163 (6)	0.0193 (6)	0.0222 (6)	0.0001 (5)	0.0003 (5)	−0.0021 (5)
C39	0.0175 (6)	0.0325 (7)	0.0258 (7)	0.0033 (5)	0.0033 (5)	−0.0013 (6)
C32	0.0152 (6)	0.0178 (6)	0.0167 (6)	0.0011 (5)	0.0015 (4)	−0.0003 (5)
C53	0.0209 (6)	0.0265 (7)	0.0264 (7)	−0.0045 (5)	0.0001 (5)	0.0027 (5)
C38	0.0218 (7)	0.0453 (9)	0.0245 (7)	0.0047 (6)	−0.0023 (5)	−0.0015 (6)
C511	0.0240 (7)	0.0426 (8)	0.0220 (7)	−0.0002 (6)	0.0003 (5)	0.0053 (6)
O61	0.0178 (4)	0.0199 (4)	0.0201 (4)	0.0030 (3)	0.0051 (3)	0.0015 (3)
O64	0.0210 (5)	0.0501 (6)	0.0242 (5)	−0.0092 (4)	0.0054 (4)	0.0043 (5)
O63	0.0277 (5)	0.0389 (6)	0.0208 (5)	−0.0022 (4)	−0.0005 (4)	−0.0014 (4)
C63	0.0205 (6)	0.0139 (5)	0.0219 (6)	0.0001 (5)	0.0044 (5)	0.0010 (5)
C70	0.0220 (6)	0.0153 (6)	0.0210 (6)	0.0019 (5)	0.0041 (5)	0.0010 (5)
C62	0.0179 (6)	0.0175 (6)	0.0173 (6)	0.0008 (5)	0.0028 (4)	0.0006 (5)
C76	0.0209 (6)	0.0213 (6)	0.0202 (6)	−0.0002 (5)	0.0027 (5)	0.0004 (5)
C77	0.0193 (6)	0.0175 (6)	0.0235 (6)	−0.0004 (5)	0.0051 (5)	0.0012 (5)
C64	0.0211 (6)	0.0191 (6)	0.0224 (6)	−0.0015 (5)	0.0049 (5)	0.0011 (5)
C66	0.0224 (6)	0.0279 (7)	0.0233 (7)	−0.0007 (5)	0.0061 (5)	0.0029 (5)
C75	0.0281 (7)	0.0203 (6)	0.0237 (6)	0.0050 (5)	0.0015 (5)	−0.0017 (5)
C65	0.0203 (6)	0.0160 (6)	0.0228 (6)	0.0004 (5)	0.0040 (5)	0.0013 (5)
C74	0.0316 (7)	0.0157 (6)	0.0243 (6)	−0.0016 (5)	−0.0041 (5)	0.0006 (5)
C73	0.0230 (6)	0.0218 (6)	0.0255 (7)	−0.0058 (5)	−0.0009 (5)	0.0038 (5)
C78	0.0186 (6)	0.0176 (6)	0.0239 (6)	0.0016 (5)	0.0025 (5)	−0.0003 (5)
C71	0.0200 (6)	0.0179 (6)	0.0151 (6)	−0.0019 (5)	0.0001 (4)	0.0003 (5)
C69	0.0188 (6)	0.0368 (8)	0.0280 (7)	0.0006 (6)	0.0038 (5)	0.0043 (6)
C83	0.0206 (6)	0.0253 (7)	0.0267 (7)	−0.0034 (5)	0.0020 (5)	0.0033 (5)
C79	0.0235 (6)	0.0193 (6)	0.0243 (6)	−0.0030 (5)	0.0008 (5)	0.0006 (5)
C72	0.0202 (6)	0.0207 (6)	0.0215 (6)	−0.0003 (5)	0.0022 (5)	0.0007 (5)
C82	0.0215 (6)	0.0286 (7)	0.0269 (7)	−0.0043 (5)	−0.0021 (5)	−0.0007 (6)
C80	0.0247 (7)	0.0233 (6)	0.0237 (7)	−0.0010 (5)	0.0033 (5)	0.0027 (5)
C68	0.0210 (7)	0.0527 (10)	0.0277 (7)	−0.0027 (6)	−0.0026 (5)	0.0051 (7)
C811	0.0291 (7)	0.0505 (9)	0.0214 (7)	−0.0002 (7)	0.0030 (5)	0.0030 (6)
C67	0.0279 (7)	0.0454 (8)	0.0208 (7)	−0.0024 (6)	0.0020 (5)	0.0048 (6)
C81	0.0220 (6)	0.0243 (6)	0.0215 (6)	0.0043 (5)	0.0000 (5)	−0.0004 (5)

Geometric parameters (Å, º)

O1—C10	1.3623 (15)	C52—C53	1.374 (2)
O1—C2	1.4600 (14)	C52—C51	1.398 (2)
O4—C4	1.2287 (16)	C52—H52	0.9500
O3—C21	1.3565 (16)	C35—C34	1.4730 (17)
O3—C211	1.4308 (18)	C43—C44	1.383 (2)
C5—C10	1.4000 (18)	C43—H43	0.9500
C5—C6	1.4038 (19)	C45—C44	1.391 (2)
C5—C4	1.4717 (17)	C45—H45	0.9500
C4—C3	1.4941 (17)	C37—C38	1.400 (2)
C6—C7	1.3786 (19)	C37—H37	0.9500
C6—H6	0.9500	C51—C50	1.3959 (18)
C3—C17	1.3451 (18)	C50—C49	1.3952 (18)
C3—C2	1.5052 (16)	C50—H50	0.9500
C17—C18	1.4597 (18)	C44—H44	0.9500
C17—H17	0.9500	C49—H49	0.9500
C21—C22	1.395 (2)	C39—C38	1.379 (2)
C21—C20	1.3983 (18)	C39—H39	0.9500
C9—C8	1.383 (2)	C32—H32	1.0000
C9—C10	1.3923 (18)	C53—H53	0.9500
C9—H9	0.9500	C38—H38	0.9500
C19—C20	1.3919 (18)	C511—H51A	0.9800
C19—C18	1.4007 (18)	C511—H51B	0.9800
C19—H19	0.9500	C511—H51C	0.9800
C23—C22	1.3778 (19)	O61—C70	1.3656 (16)
C23—C18	1.4082 (18)	O61—C62	1.4592 (14)
C23—H23	0.9500	O64—C64	1.2284 (16)
C16—C15	1.3910 (19)	O63—C81	1.3597 (16)
C16—C11	1.3946 (18)	O63—C811	1.4345 (18)
C16—H16	0.9500	C63—C77	1.3466 (18)
C2—C11	1.5218 (17)	C63—C64	1.4902 (18)
C2—H2	1.0000	C63—C62	1.5072 (17)
C14—C15	1.387 (2)	C70—C69	1.3927 (19)
C14—C13	1.389 (2)	C70—C65	1.3953 (18)
C14—H14	0.9500	C62—C71	1.5205 (17)
C15—H15	0.9500	C62—H62	1.0000
C11—C12	1.3902 (18)	C76—C71	1.3904 (18)
C12—C13	1.3953 (19)	C76—C75	1.3954 (19)
C12—H12	0.9500	C76—H76	0.9500
C20—H20	0.9500	C77—C78	1.4576 (18)
C13—H13	0.9500	C77—H77	0.9500
C8—C7	1.396 (2)	C64—C65	1.4738 (18)
C8—H8	0.9500	C66—C67	1.378 (2)
C22—H22	0.9500	C66—C65	1.4013 (19)
C7—H7	0.9500	C66—H66	0.9500
C211—H21A	0.9800	C75—C74	1.384 (2)
C211—H21B	0.9800	C75—H75	0.9500
C211—H21C	0.9800	C74—C73	1.390 (2)
O31—C40	1.3631 (15)	C74—H74	0.9500
O31—C32	1.4584 (14)	C73—C72	1.3855 (19)
O34—C34	1.2299 (16)	C73—H73	0.9500
C40—C39	1.3948 (18)	C78—C79	1.3998 (18)
C40—C35	1.3970 (18)	C78—C83	1.4020 (19)
O33—C51	1.3572 (16)	C71—C72	1.3982 (18)
O33—C511	1.4271 (18)	C69—C68	1.377 (2)
C41—C42	1.3900 (18)	C69—H69	0.9500
C41—C46	1.3953 (18)	C83—C82	1.377 (2)
C41—C32	1.5174 (17)	C83—H83	0.9500
C42—C43	1.3939 (19)	C79—C80	1.3896 (19)
C42—H42	0.9500	C79—H79	0.9500
C33—C47	1.3453 (18)	C72—H72	0.9500
C33—C34	1.4918 (17)	C82—C81	1.393 (2)
C33—C32	1.5057 (16)	C82—H82	0.9500
C46—C45	1.384 (2)	C80—C81	1.3932 (19)
C46—H46	0.9500	C80—H80	0.9500
C48—C49	1.3998 (18)	C68—C67	1.397 (2)
C48—C53	1.4061 (18)	C68—H68	0.9500
C48—C47	1.4619 (18)	C811—H81A	0.9800
C36—C37	1.3779 (19)	C811—H81B	0.9800
C36—C35	1.4051 (18)	C811—H81C	0.9800
C36—H36	0.9500	C67—H67	0.9500
C47—H47	0.9500
C10—O1—C2	117.97 (9)	C46—C45—H45	120.1
C21—O3—C211	117.40 (11)	C44—C45—H45	120.1
C10—C5—C6	118.91 (12)	C36—C37—C38	119.56 (13)
C10—C5—C4	120.07 (11)	C36—C37—H37	120.2
C6—C5—C4	120.90 (12)	C38—C37—H37	120.2
O4—C4—C5	121.84 (12)	O33—C51—C50	125.32 (12)
O4—C4—C3	122.08 (11)	O33—C51—C52	115.40 (12)
C5—C4—C3	116.05 (11)	C50—C51—C52	119.28 (12)
C7—C6—C5	120.50 (13)	C49—C50—C51	119.85 (12)
C7—C6—H6	119.8	C49—C50—H50	120.1
C5—C6—H6	119.8	C51—C50—H50	120.1
C17—C3—C4	117.37 (11)	C43—C44—C45	120.09 (13)
C17—C3—C2	125.02 (11)	C43—C44—H44	120.0
C4—C3—C2	117.61 (10)	C45—C44—H44	120.0
C3—C17—C18	132.39 (11)	C50—C49—C48	121.62 (12)
C3—C17—H17	113.8	C50—C49—H49	119.2
C18—C17—H17	113.8	C48—C49—H49	119.2
O3—C21—C22	115.51 (12)	C38—C39—C40	119.20 (12)
O3—C21—C20	125.13 (12)	C38—C39—H39	120.4
C22—C21—C20	119.35 (12)	C40—C39—H39	120.4
C8—C9—C10	119.21 (12)	O31—C32—C33	112.68 (10)
C8—C9—H9	120.4	O31—C32—C41	107.63 (9)
C10—C9—H9	120.4	C33—C32—C41	114.85 (10)
C20—C19—C18	121.50 (11)	O31—C32—H32	107.1
C20—C19—H19	119.2	C33—C32—H32	107.1
C18—C19—H19	119.2	C41—C32—H32	107.1
C22—C23—C18	122.06 (12)	C52—C53—C48	122.15 (13)
C22—C23—H23	119.0	C52—C53—H53	118.9
C18—C23—H23	119.0	C48—C53—H53	118.9
C19—C18—C23	117.07 (12)	C39—C38—C37	121.05 (12)
C19—C18—C17	126.57 (11)	C39—C38—H38	119.5
C23—C18—C17	116.33 (11)	C37—C38—H38	119.5
C15—C16—C11	120.38 (12)	O33—C511—H51A	109.5
C15—C16—H16	119.8	O33—C511—H51B	109.5
C11—C16—H16	119.8	H51A—C511—H51B	109.5
O1—C2—C3	112.32 (9)	O33—C511—H51C	109.5
O1—C2—C11	107.50 (9)	H51A—C511—H51C	109.5
C3—C2—C11	114.82 (10)	H51B—C511—H51C	109.5
O1—C2—H2	107.3	C70—O61—C62	116.70 (9)
C3—C2—H2	107.3	C81—O63—C811	117.16 (11)
C11—C2—H2	107.3	C77—C63—C64	117.28 (11)
C15—C14—C13	120.21 (12)	C77—C63—C62	125.43 (11)
C15—C14—H14	119.9	C64—C63—C62	117.27 (11)
C13—C14—H14	119.9	O61—C70—C69	117.16 (11)
C14—C15—C16	119.80 (13)	O61—C70—C65	122.19 (11)
C14—C15—H15	120.1	C69—C70—C65	120.56 (12)
C16—C15—H15	120.1	O61—C62—C63	111.65 (10)
O1—C10—C9	116.44 (11)	O61—C62—C71	107.38 (10)
O1—C10—C5	122.73 (11)	C63—C62—C71	115.04 (10)
C9—C10—C5	120.74 (12)	O61—C62—H62	107.5
C12—C11—C16	119.55 (12)	C63—C62—H62	107.5
C12—C11—C2	122.99 (11)	C71—C62—H62	107.5
C16—C11—C2	117.45 (11)	C71—C76—C75	119.88 (12)
C11—C12—C13	120.08 (12)	C71—C76—H76	120.1
C11—C12—H12	120.0	C75—C76—H76	120.1
C13—C12—H12	120.0	C63—C77—C78	132.10 (12)
C19—C20—C21	120.00 (12)	C63—C77—H77	114.0
C19—C20—H20	120.0	C78—C77—H77	114.0
C21—C20—H20	120.0	O64—C64—C65	121.73 (12)
C14—C13—C12	119.96 (13)	O64—C64—C63	121.96 (12)
C14—C13—H13	120.0	C65—C64—C63	116.29 (11)
C12—C13—H13	120.0	C67—C66—C65	120.28 (12)
C9—C8—C7	120.96 (13)	C67—C66—H66	119.9
C9—C8—H8	119.5	C65—C66—H66	119.9
C7—C8—H8	119.5	C74—C75—C76	120.42 (13)
C23—C22—C21	120.01 (12)	C74—C75—H75	119.8
C23—C22—H22	120.0	C76—C75—H75	119.8
C21—C22—H22	120.0	C70—C65—C66	119.30 (12)
C6—C7—C8	119.69 (13)	C70—C65—C64	119.75 (11)
C6—C7—H7	120.2	C66—C65—C64	120.87 (11)
C8—C7—H7	120.2	C75—C74—C73	119.94 (12)
O3—C211—H21A	109.5	C75—C74—H74	120.0
O3—C211—H21B	109.5	C73—C74—H74	120.0
H21A—C211—H21B	109.5	C72—C73—C74	119.84 (12)
O3—C211—H21C	109.5	C72—C73—H73	120.1
H21A—C211—H21C	109.5	C74—C73—H73	120.1
H21B—C211—H21C	109.5	C79—C78—C83	117.02 (12)
C40—O31—C32	117.69 (9)	C79—C78—C77	126.46 (12)
O31—C40—C39	116.48 (11)	C83—C78—C77	116.50 (11)
O31—C40—C35	122.69 (11)	C76—C71—C72	119.30 (12)
C39—C40—C35	120.73 (12)	C76—C71—C62	123.07 (11)
C51—O33—C511	118.08 (11)	C72—C71—C62	117.61 (11)
C42—C41—C46	119.40 (12)	C68—C69—C70	119.13 (13)
C42—C41—C32	123.58 (12)	C68—C69—H69	120.4
C46—C41—C32	117.02 (11)	C70—C69—H69	120.4
C41—C42—C43	120.03 (13)	C82—C83—C78	122.35 (12)
C41—C42—H42	120.0	C82—C83—H83	118.8
C43—C42—H42	120.0	C78—C83—H83	118.8
C47—C33—C34	118.04 (11)	C80—C79—C78	121.33 (12)
C47—C33—C32	124.20 (11)	C80—C79—H79	119.3
C34—C33—C32	117.76 (10)	C78—C79—H79	119.3
C45—C46—C41	120.51 (13)	C73—C72—C71	120.60 (12)
C45—C46—H46	119.7	C73—C72—H72	119.7
C41—C46—H46	119.7	C71—C72—H72	119.7
C49—C48—C53	117.00 (12)	C83—C82—C81	119.67 (12)
C49—C48—C47	126.19 (11)	C83—C82—H82	120.2
C53—C48—C47	116.77 (11)	C81—C82—H82	120.2
C37—C36—C35	120.48 (12)	C79—C80—C81	120.11 (12)
C37—C36—H36	119.8	C79—C80—H80	119.9
C35—C36—H36	119.8	C81—C80—H80	119.9
C33—C47—C48	131.28 (12)	C69—C68—C67	121.23 (13)
C33—C47—H47	114.4	C69—C68—H68	119.4
C48—C47—H47	114.4	C67—C68—H68	119.4
C53—C52—C51	120.09 (12)	O63—C811—H81A	109.5
C53—C52—H52	120.0	O63—C811—H81B	109.5
C51—C52—H52	120.0	H81A—C811—H81B	109.5
C40—C35—C36	118.98 (12)	O63—C811—H81C	109.5
C40—C35—C34	120.14 (11)	H81A—C811—H81C	109.5
C36—C35—C34	120.78 (11)	H81B—C811—H81C	109.5
C44—C43—C42	120.14 (13)	C66—C67—C68	119.50 (13)
C44—C43—H43	119.9	C66—C67—H67	120.3
C42—C43—H43	119.9	C68—C67—H67	120.3
O34—C34—C35	121.95 (12)	O63—C81—C82	115.48 (12)
O34—C34—C33	121.99 (11)	O63—C81—C80	125.02 (12)
C35—C34—C33	116.04 (11)	C82—C81—C80	119.50 (12)
C46—C45—C44	119.82 (13)
C10—C5—C4—O4	172.55 (12)	C511—O33—C51—C52	172.73 (12)
C6—C5—C4—O4	−3.4 (2)	C53—C52—C51—O33	−177.89 (13)
C10—C5—C4—C3	−5.40 (17)	C53—C52—C51—C50	1.6 (2)
C6—C5—C4—C3	178.69 (11)	O33—C51—C50—C49	177.97 (12)
C10—C5—C6—C7	−0.1 (2)	C52—C51—C50—C49	−1.43 (19)
C4—C5—C6—C7	175.82 (13)	C42—C43—C44—C45	0.6 (2)
O4—C4—C3—C17	−12.43 (18)	C46—C45—C44—C43	−0.5 (2)
C5—C4—C3—C17	165.51 (11)	C51—C50—C49—C48	0.45 (19)
O4—C4—C3—C2	168.13 (12)	C53—C48—C49—C50	0.38 (18)
C5—C4—C3—C2	−13.93 (16)	C47—C48—C49—C50	−177.01 (12)
C4—C3—C17—C18	−179.20 (12)	O31—C40—C39—C38	−176.80 (12)
C2—C3—C17—C18	0.2 (2)	C35—C40—C39—C38	−0.4 (2)
C211—O3—C21—C22	173.76 (12)	C40—O31—C32—C33	−42.30 (14)
C211—O3—C21—C20	−6.13 (19)	C40—O31—C32—C41	85.35 (12)
C20—C19—C18—C23	−0.82 (18)	C47—C33—C32—O31	−145.24 (12)
C20—C19—C18—C17	−178.53 (12)	C34—C33—C32—O31	34.79 (14)
C22—C23—C18—C19	0.60 (19)	C47—C33—C32—C41	91.03 (15)
C22—C23—C18—C17	178.55 (12)	C34—C33—C32—C41	−88.94 (13)
C3—C17—C18—C19	−18.2 (2)	C42—C41—C32—O31	−117.82 (12)
C3—C17—C18—C23	164.12 (13)	C46—C41—C32—O31	62.14 (14)
C10—O1—C2—C3	−42.24 (14)	C42—C41—C32—C33	8.55 (17)
C10—O1—C2—C11	85.01 (12)	C46—C41—C32—C33	−171.49 (11)
C17—C3—C2—O1	−142.84 (12)	C51—C52—C53—C48	−0.7 (2)
C4—C3—C2—O1	36.55 (14)	C49—C48—C53—C52	−0.2 (2)
C17—C3—C2—C11	93.93 (14)	C47—C48—C53—C52	177.40 (13)
C4—C3—C2—C11	−86.68 (13)	C40—C39—C38—C37	0.0 (2)
C13—C14—C15—C16	−0.7 (2)	C36—C37—C38—C39	0.2 (2)
C11—C16—C15—C14	−0.1 (2)	C62—O61—C70—C69	−153.01 (11)
C2—O1—C10—C9	−158.52 (11)	C62—O61—C70—C65	30.56 (16)
C2—O1—C10—C5	24.89 (16)	C70—O61—C62—C63	−47.30 (13)
C8—C9—C10—O1	−176.47 (12)	C70—O61—C62—C71	79.67 (12)
C8—C9—C10—C5	0.2 (2)	C77—C63—C62—O61	−141.66 (12)
C6—C5—C10—O1	176.38 (11)	C64—C63—C62—O61	36.81 (14)
C4—C5—C10—O1	0.38 (18)	C77—C63—C62—C71	95.64 (15)
C6—C5—C10—C9	−0.07 (19)	C64—C63—C62—C71	−85.89 (13)
C4—C5—C10—C9	−176.07 (12)	C64—C63—C77—C78	−177.96 (12)
C15—C16—C11—C12	0.72 (19)	C62—C63—C77—C78	0.5 (2)
C15—C16—C11—C2	−177.83 (12)	C77—C63—C64—O64	−10.26 (19)
O1—C2—C11—C12	−114.83 (12)	C62—C63—C64—O64	171.15 (12)
C3—C2—C11—C12	10.94 (17)	C77—C63—C64—C65	168.52 (11)
O1—C2—C11—C16	63.66 (14)	C62—C63—C64—C65	−10.07 (16)
C3—C2—C11—C16	−170.57 (10)	C71—C76—C75—C74	0.3 (2)
C16—C11—C12—C13	−0.59 (18)	O61—C70—C65—C66	176.02 (11)
C2—C11—C12—C13	177.87 (11)	C69—C70—C65—C66	−0.30 (19)
C18—C19—C20—C21	0.85 (19)	O61—C70—C65—C64	−0.83 (18)
O3—C21—C20—C19	179.27 (12)	C69—C70—C65—C64	−177.15 (12)
C22—C21—C20—C19	−0.62 (19)	C67—C66—C65—C70	0.9 (2)
C15—C14—C13—C12	0.8 (2)	C67—C66—C65—C64	177.67 (13)
C11—C12—C13—C14	−0.16 (19)	O64—C64—C65—C70	169.77 (13)
C10—C9—C8—C7	−0.1 (2)	C63—C64—C65—C70	−9.01 (17)
C18—C23—C22—C21	−0.4 (2)	O64—C64—C65—C66	−7.0 (2)
O3—C21—C22—C23	−179.49 (12)	C63—C64—C65—C66	174.19 (11)
C20—C21—C22—C23	0.4 (2)	C76—C75—C74—C73	0.5 (2)
C5—C6—C7—C8	0.2 (2)	C75—C74—C73—C72	−0.4 (2)
C9—C8—C7—C6	−0.1 (2)	C63—C77—C78—C79	−21.0 (2)
C32—O31—C40—C39	−157.69 (11)	C63—C77—C78—C83	160.18 (14)
C32—O31—C40—C35	25.97 (16)	C75—C76—C71—C72	−1.11 (19)
C46—C41—C42—C43	−0.85 (18)	C75—C76—C71—C62	177.25 (12)
C32—C41—C42—C43	179.11 (12)	O61—C62—C71—C76	−119.98 (12)
C42—C41—C46—C45	1.01 (19)	C63—C62—C71—C76	4.98 (17)
C32—C41—C46—C45	−178.95 (12)	O61—C62—C71—C72	58.40 (14)
C34—C33—C47—C48	177.83 (12)	C63—C62—C71—C72	−176.64 (11)
C32—C33—C47—C48	−2.1 (2)	O61—C70—C69—C68	−176.75 (13)
C49—C48—C47—C33	−20.9 (2)	C65—C70—C69—C68	−0.3 (2)
C53—C48—C47—C33	161.75 (14)	C79—C78—C83—C82	1.7 (2)
O31—C40—C35—C36	176.70 (11)	C77—C78—C83—C82	−179.34 (12)
C39—C40—C35—C36	0.51 (19)	C83—C78—C79—C80	−1.62 (19)
O31—C40—C35—C34	0.11 (19)	C77—C78—C79—C80	179.56 (12)
C39—C40—C35—C34	−176.08 (12)	C74—C73—C72—C71	−0.5 (2)
C37—C36—C35—C40	−0.3 (2)	C76—C71—C72—C73	1.22 (19)
C37—C36—C35—C34	176.28 (13)	C62—C71—C72—C73	−177.23 (12)
C41—C42—C43—C44	0.0 (2)	C78—C83—C82—C81	−0.6 (2)
C40—C35—C34—O34	171.68 (12)	C78—C79—C80—C81	0.5 (2)
C36—C35—C34—O34	−4.8 (2)	C70—C69—C68—C67	0.3 (2)
C40—C35—C34—C33	−7.01 (17)	C65—C66—C67—C68	−0.8 (2)
C36—C35—C34—C33	176.46 (11)	C69—C68—C67—C66	0.3 (3)
C47—C33—C34—O34	−9.97 (18)	C811—O63—C81—C82	176.45 (12)
C32—C33—C34—O34	170.01 (12)	C811—O63—C81—C80	−3.50 (19)
C47—C33—C34—C35	168.73 (11)	C83—C82—C81—O63	179.47 (12)
C32—C33—C34—C35	−11.30 (16)	C83—C82—C81—C80	−0.6 (2)
C41—C46—C45—C44	−0.4 (2)	C79—C80—C81—O63	−179.39 (12)
C35—C36—C37—C38	0.0 (2)	C79—C80—C81—C82	0.7 (2)
C511—O33—C51—C50	−6.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O34^i	1.00	2.45	3.3434 (15)	148
C6—H6···O61^ii	0.95	2.40	3.2676 (16)	151
C14—H14···O1^iii	0.95	2.46	3.3750 (15)	161
C32—H32···O64^iv	1.00	2.37	3.2348 (15)	144
C36—H36···O1^v	0.95	2.42	3.2733 (15)	150
C44—H44···O31^iii	0.95	2.42	3.3399 (16)	162
C62—H62···O4^vi	1.00	2.48	3.3629 (15)	146
C66—H66···O31^vii	0.95	2.48	3.3725 (15)	157
C74—H74···O61^iii	0.95	2.49	3.4018 (15)	161

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

(E)-3-Benzylidenechroman-4-one (compound_V_AAG5)

Crystal data

C16H12O2	Z = 2
Mr = 236.26	F(000) = 248
Triclinic, P1	Dx = 1.347 Mg m^−3
a = 7.7718 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.6069 (3) Å	Cell parameters from 3741 reflections
c = 9.0857 (3) Å	θ = 3.7–35.8°
α = 89.744 (3)°	µ = 0.09 mm^−1
β = 84.862 (3)°	T = 100 K
γ = 74.199 (3)°	Needle, colorless
V = 582.31 (4) Å^3	0.18 × 0.08 × 0.08 mm

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	2425 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	2120 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.023
Detector resolution: 10.4498 pixels mm^-1	θmax = 26.5°, θmin = 3.3°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −9→10
Tmin = 0.865, Tmax = 1.000	l = −11→11
4947 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.115	w = 1/[σ^2(Fo^2) + (0.0597P)^2 + 0.1583P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2425 reflections	Δρmax = 0.29 e Å^−3
163 parameters	Δρmin = −0.22 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
O1	0.56491 (12)	0.96012 (10)	0.67017 (9)	0.0203 (2)
O4	0.31184 (12)	0.69758 (10)	0.94932 (9)	0.0221 (2)
C9	0.43926 (16)	1.03656 (15)	0.78021 (13)	0.0174 (3)
C4	0.38354 (17)	0.77597 (15)	0.86245 (13)	0.0175 (3)
C12	0.74274 (17)	0.43694 (14)	0.64267 (13)	0.0182 (3)
C3	0.52016 (17)	0.69819 (15)	0.73982 (13)	0.0172 (3)
C10	0.34234 (16)	0.95369 (14)	0.87368 (13)	0.0177 (3)
C8	0.41493 (18)	1.20162 (15)	0.79971 (14)	0.0208 (3)
H8	0.4843	1.2560	0.7383	0.025*
C11	0.60958 (17)	0.54181 (15)	0.74961 (13)	0.0181 (3)
H11	0.5826	0.4918	0.8389	0.022*
C5	0.21682 (17)	1.04169 (16)	0.98441 (14)	0.0207 (3)
H5	0.1504	0.9873	1.0488	0.025*
C13	0.74448 (17)	0.45644 (15)	0.48910 (14)	0.0201 (3)
H13	0.6581	0.5435	0.4503	0.024*
C6	0.18851 (18)	1.20637 (16)	1.00108 (14)	0.0236 (3)
H6	0.1009	1.2652	1.0748	0.028*
C17	0.87029 (18)	0.30509 (15)	0.69590 (14)	0.0225 (3)
H17	0.8701	0.2881	0.7993	0.027*
C7	0.28933 (18)	1.28633 (15)	0.90890 (14)	0.0225 (3)
H7	0.2714	1.3993	0.9214	0.027*
C2	0.54324 (18)	0.80948 (14)	0.61596 (13)	0.0194 (3)
H2A	0.6499	0.7553	0.5486	0.023*
H2B	0.4369	0.8322	0.5587	0.023*
C16	0.99632 (18)	0.19957 (16)	0.59981 (16)	0.0262 (3)
H16	1.0826	0.1117	0.6377	0.031*
C15	0.99711 (18)	0.22168 (16)	0.44774 (16)	0.0257 (3)
H15	1.0836	0.1492	0.3819	0.031*
C14	0.87098 (18)	0.35004 (16)	0.39325 (15)	0.0234 (3)
H14	0.8711	0.3653	0.2896	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0259 (5)	0.0181 (4)	0.0172 (4)	−0.0084 (4)	0.0039 (3)	0.0016 (3)
O4	0.0288 (5)	0.0228 (5)	0.0160 (4)	−0.0104 (4)	0.0013 (4)	0.0049 (3)
C9	0.0191 (6)	0.0210 (6)	0.0126 (5)	−0.0055 (5)	−0.0035 (4)	0.0035 (4)
C4	0.0207 (6)	0.0212 (6)	0.0126 (6)	−0.0080 (5)	−0.0045 (4)	0.0047 (4)
C12	0.0199 (6)	0.0184 (6)	0.0185 (6)	−0.0085 (5)	−0.0026 (5)	0.0024 (5)
C3	0.0213 (6)	0.0201 (6)	0.0125 (6)	−0.0094 (5)	−0.0017 (4)	0.0024 (4)
C10	0.0201 (6)	0.0200 (6)	0.0142 (6)	−0.0063 (5)	−0.0046 (5)	0.0031 (5)
C8	0.0261 (7)	0.0211 (6)	0.0177 (6)	−0.0098 (5)	−0.0057 (5)	0.0057 (5)
C11	0.0232 (6)	0.0210 (6)	0.0128 (6)	−0.0098 (5)	−0.0040 (5)	0.0039 (5)
C5	0.0209 (6)	0.0250 (6)	0.0166 (6)	−0.0071 (5)	−0.0017 (5)	0.0035 (5)
C13	0.0219 (6)	0.0208 (6)	0.0185 (6)	−0.0064 (5)	−0.0041 (5)	0.0022 (5)
C6	0.0233 (7)	0.0256 (7)	0.0197 (6)	−0.0029 (5)	−0.0014 (5)	−0.0013 (5)
C17	0.0248 (7)	0.0236 (6)	0.0206 (6)	−0.0086 (5)	−0.0043 (5)	0.0055 (5)
C7	0.0282 (7)	0.0181 (6)	0.0215 (6)	−0.0053 (5)	−0.0077 (5)	0.0019 (5)
C2	0.0267 (7)	0.0184 (6)	0.0138 (6)	−0.0076 (5)	0.0000 (5)	0.0022 (5)
C16	0.0227 (7)	0.0230 (7)	0.0312 (7)	−0.0026 (5)	−0.0050 (5)	0.0040 (5)
C15	0.0204 (7)	0.0268 (7)	0.0290 (7)	−0.0066 (5)	0.0029 (5)	−0.0045 (5)
C14	0.0256 (7)	0.0279 (7)	0.0183 (6)	−0.0105 (5)	0.0001 (5)	−0.0013 (5)

Geometric parameters (Å, º)

O1—C9	1.3664 (14)	C5—C6	1.3808 (18)
O1—C2	1.4462 (14)	C5—H5	0.9500
O4—C4	1.2288 (15)	C13—C14	1.3882 (18)
C9—C8	1.3912 (17)	C13—H13	0.9500
C9—C10	1.4035 (17)	C6—C7	1.4000 (19)
C4—C10	1.4770 (17)	C6—H6	0.9500
C4—C3	1.4915 (17)	C17—C16	1.3842 (18)
C12—C13	1.4040 (17)	C17—H17	0.9500
C12—C17	1.4045 (17)	C7—H7	0.9500
C12—C11	1.4659 (17)	C2—H2A	0.9900
C3—C11	1.3428 (17)	C2—H2B	0.9900
C3—C2	1.5046 (16)	C16—C15	1.394 (2)
C10—C5	1.4022 (17)	C16—H16	0.9500
C8—C7	1.3834 (18)	C15—C14	1.3852 (19)
C8—H8	0.9500	C15—H15	0.9500
C11—H11	0.9500	C14—H14	0.9500
C9—O1—C2	115.34 (9)	C14—C13—H13	119.6
O1—C9—C8	116.88 (11)	C12—C13—H13	119.6
O1—C9—C10	122.40 (11)	C5—C6—C7	119.76 (12)
C8—C9—C10	120.69 (12)	C5—C6—H6	120.1
O4—C4—C10	122.27 (11)	C7—C6—H6	120.1
O4—C4—C3	122.37 (11)	C16—C17—C12	120.92 (12)
C10—C4—C3	115.35 (10)	C16—C17—H17	119.5
C13—C12—C17	118.03 (11)	C12—C17—H17	119.5
C13—C12—C11	123.52 (11)	C8—C7—C6	120.34 (12)
C17—C12—C11	118.37 (11)	C8—C7—H7	119.8
C11—C3—C4	118.95 (11)	C6—C7—H7	119.8
C11—C3—C2	126.81 (11)	O1—C2—C3	111.90 (10)
C4—C3—C2	114.23 (10)	O1—C2—H2A	109.2
C5—C10—C9	118.55 (11)	C3—C2—H2A	109.2
C5—C10—C4	121.13 (11)	O1—C2—H2B	109.2
C9—C10—C4	120.13 (11)	C3—C2—H2B	109.2
C7—C8—C9	119.77 (11)	H2A—C2—H2B	107.9
C7—C8—H8	120.1	C17—C16—C15	120.25 (12)
C9—C8—H8	120.1	C17—C16—H16	119.9
C3—C11—C12	129.45 (11)	C15—C16—H16	119.9
C3—C11—H11	115.3	C14—C15—C16	119.59 (12)
C12—C11—H11	115.3	C14—C15—H15	120.2
C6—C5—C10	120.84 (12)	C16—C15—H15	120.2
C6—C5—H5	119.6	C15—C14—C13	120.42 (12)
C10—C5—H5	119.6	C15—C14—H14	119.8
C14—C13—C12	120.78 (12)	C13—C14—H14	119.8
C2—O1—C9—C8	−158.11 (11)	C13—C12—C11—C3	−29.7 (2)
C2—O1—C9—C10	24.05 (16)	C17—C12—C11—C3	153.47 (13)
O4—C4—C3—C11	−21.46 (17)	C9—C10—C5—C6	0.20 (18)
C10—C4—C3—C11	157.66 (11)	C4—C10—C5—C6	175.21 (11)
O4—C4—C3—C2	159.17 (12)	C17—C12—C13—C14	−1.21 (18)
C10—C4—C3—C2	−21.72 (14)	C11—C12—C13—C14	−178.02 (11)
O1—C9—C10—C5	179.55 (10)	C10—C5—C6—C7	−1.62 (19)
C8—C9—C10—C5	1.79 (18)	C13—C12—C17—C16	1.34 (18)
O1—C9—C10—C4	4.49 (18)	C11—C12—C17—C16	178.32 (11)
C8—C9—C10—C4	−173.27 (11)	C9—C8—C7—C6	0.90 (19)
O4—C4—C10—C5	−0.65 (18)	C5—C6—C7—C8	1.08 (19)
C3—C4—C10—C5	−179.76 (10)	C9—O1—C2—C3	−50.13 (14)
O4—C4—C10—C9	174.29 (11)	C11—C3—C2—O1	−130.51 (13)
C3—C4—C10—C9	−4.83 (16)	C4—C3—C2—O1	48.81 (14)
O1—C9—C8—C7	179.78 (11)	C12—C17—C16—C15	−0.8 (2)
C10—C9—C8—C7	−2.35 (18)	C17—C16—C15—C14	0.0 (2)
C4—C3—C11—C12	177.04 (11)	C16—C15—C14—C13	0.1 (2)
C2—C3—C11—C12	−3.7 (2)	C12—C13—C14—C15	0.52 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O4^i	0.95	2.56	3.4153 (15)	150
C17—H17···O4^i	0.95	2.56	3.4050 (16)	148
C7—H7···O4^ii	0.95	2.69	3.6131 (16)	166

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

(E)-3-(4-Methoxybenzylidene)chroman-4-one (AAG4)

Crystal data

C17H14O3	Z = 4
Mr = 266.28	F(000) = 560
Triclinic, P1	Dx = 1.368 Mg m^−3
a = 7.5570 (3) Å	Cu Kα radiation, λ = 1.54184 Å
b = 12.3558 (4) Å	Cell parameters from 8925 reflections
c = 14.4044 (6) Å	θ = 3.7–71.9°
α = 82.748 (3)°	µ = 0.76 mm^−1
β = 87.126 (3)°	T = 100 K
γ = 75.768 (3)°	Needle, colorless
V = 1293.02 (9) Å^3	0.3 × 0.08 × 0.06 mm

Data collection

XtaLAB Synergy Dualflex HyPix diffractometer	5118 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	4669 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.020
Detector resolution: 10.0000 pixels mm^-1	θmax = 66.6°, θmin = 3.1°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2019)	k = −14→14
Tmin = 0.671, Tmax = 1.000	l = −17→17
5118 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.070	H-atom parameters constrained
wR(F^2) = 0.200	w = 1/[σ^2(Fo^2) + (0.1415P)^2 + 0.4525P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
5118 reflections	Δρmax = 0.63 e Å^−3
364 parameters	Δρmin = −0.33 e Å^−3

Special details

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

Refinement. Refined as a 2-component twin.

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

	x	y	z	Uiso*/Ueq
O22	0.4818 (3)	0.40499 (15)	0.86434 (13)	0.0291 (4)
O21	−0.0050 (2)	−0.08126 (14)	0.93266 (12)	0.0242 (4)
O24	0.4539 (3)	−0.26141 (17)	0.81175 (16)	0.0385 (5)
C32	0.4383 (3)	0.0781 (2)	0.85181 (17)	0.0219 (5)
C34	0.3282 (3)	0.2796 (2)	0.81810 (17)	0.0229 (5)
H34	0.2396	0.3429	0.7911	0.028*
C27	−0.1267 (4)	−0.3485 (2)	0.94295 (18)	0.0282 (6)
H27	−0.2211	−0.3822	0.9690	0.034*
C29	0.0045 (3)	−0.1894 (2)	0.91708 (16)	0.0217 (5)
C37	0.5883 (3)	0.0959 (2)	0.89517 (17)	0.0245 (5)
H37	0.6791	0.0328	0.9205	0.029*
C31	0.4290 (3)	−0.0379 (2)	0.84604 (17)	0.0241 (5)
H31	0.5435	−0.0899	0.8398	0.029*
C30	0.1541 (3)	−0.2517 (2)	0.86905 (17)	0.0223 (5)
C33	0.3082 (3)	0.1718 (2)	0.81231 (17)	0.0232 (5)
H33	0.2062	0.1616	0.7815	0.028*
C28	−0.1342 (4)	−0.2376 (2)	0.95432 (17)	0.0260 (5)
H28	−0.2338	−0.1951	0.9874	0.031*
C24	0.3103 (4)	−0.2035 (2)	0.83950 (18)	0.0253 (6)
C36	0.6085 (3)	0.2030 (2)	0.90225 (17)	0.0251 (5)
H36	0.7102	0.2134	0.9332	0.030*
C23	0.2839 (3)	−0.0813 (2)	0.84823 (17)	0.0229 (5)
C22	0.0881 (3)	−0.0182 (2)	0.86382 (18)	0.0242 (5)
H22A	0.0863	0.0552	0.8852	0.029*
H22B	0.0228	−0.0034	0.8039	0.029*
C35	0.4763 (3)	0.2955 (2)	0.86302 (17)	0.0233 (5)
C25	0.1572 (4)	−0.3633 (2)	0.85732 (17)	0.0249 (5)
H25	0.2560	−0.4061	0.8240	0.030*
C26	0.0184 (4)	−0.4111 (2)	0.89352 (18)	0.0276 (6)
H26	0.0213	−0.4866	0.8849	0.033*
C38	0.6384 (4)	0.4274 (2)	0.9020 (2)	0.0372 (7)
H38A	0.6447	0.4006	0.9691	0.056*
H38B	0.6293	0.5085	0.8929	0.056*
H38C	0.7487	0.3884	0.8700	0.056*
O1	0.5023 (2)	0.60541 (14)	0.43853 (12)	0.0229 (4)
O4	0.0517 (2)	0.82132 (15)	0.32039 (14)	0.0303 (5)
O2	0.0227 (3)	0.14104 (15)	0.35386 (13)	0.0298 (4)
C12	0.0649 (3)	0.4712 (2)	0.35122 (17)	0.0226 (5)
C14	0.1829 (3)	0.2797 (2)	0.31505 (17)	0.0239 (5)
H14	0.2757	0.2250	0.2883	0.029*
C3	0.2212 (3)	0.6308 (2)	0.35305 (16)	0.0217 (5)
C4	0.1961 (3)	0.7548 (2)	0.34556 (17)	0.0230 (5)
C11	0.0749 (3)	0.5888 (2)	0.34865 (17)	0.0225 (5)
H11	−0.0389	0.6428	0.3431	0.027*
C8	0.6381 (3)	0.7532 (2)	0.45601 (17)	0.0252 (5)
H8	0.7344	0.7008	0.4892	0.030*
C7	0.6363 (4)	0.8663 (2)	0.44207 (18)	0.0276 (6)
H7	0.7320	0.8916	0.4661	0.033*
C2	0.4134 (3)	0.5615 (2)	0.37033 (17)	0.0214 (5)
H2A	0.4103	0.4829	0.3930	0.026*
H2B	0.4846	0.5612	0.3107	0.026*
C15	0.0292 (3)	0.2501 (2)	0.35630 (17)	0.0241 (5)
C13	0.2016 (3)	0.3887 (2)	0.31268 (17)	0.0224 (5)
H13	0.3080	0.4080	0.2847	0.027*
C10	0.3523 (3)	0.7936 (2)	0.37333 (16)	0.0219 (5)
C5	0.3548 (3)	0.9078 (2)	0.35931 (17)	0.0235 (5)
H5	0.2587	0.9606	0.3263	0.028*
C9	0.4980 (3)	0.7173 (2)	0.42096 (16)	0.0215 (5)
C17	−0.0894 (3)	0.4396 (2)	0.39111 (17)	0.0235 (5)
H17	−0.1845	0.4945	0.4161	0.028*
C16	−0.1079 (3)	0.3297 (2)	0.39524 (18)	0.0259 (5)
H16	−0.2127	0.3093	0.4242	0.031*
C6	0.4947 (4)	0.9441 (2)	0.39283 (18)	0.0277 (6)
H6	0.4954	1.0215	0.3827	0.033*
C18	−0.1317 (4)	0.1054 (2)	0.3944 (2)	0.0360 (7)
H18A	−0.2428	0.1530	0.3650	0.054*
H18B	−0.1379	0.1117	0.4617	0.054*
H18C	−0.1208	0.0270	0.3844	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O22	0.0341 (10)	0.0234 (9)	0.0310 (10)	−0.0096 (8)	−0.0063 (8)	−0.0002 (7)
O21	0.0247 (9)	0.0204 (9)	0.0266 (9)	−0.0054 (7)	0.0066 (7)	−0.0024 (7)
O24	0.0279 (10)	0.0297 (10)	0.0585 (14)	−0.0065 (8)	0.0143 (9)	−0.0143 (9)
C32	0.0189 (11)	0.0262 (13)	0.0194 (11)	−0.0050 (9)	0.0049 (9)	−0.0010 (9)
C34	0.0221 (12)	0.0237 (12)	0.0207 (12)	−0.0038 (9)	0.0008 (9)	0.0022 (9)
C27	0.0312 (14)	0.0313 (14)	0.0245 (13)	−0.0133 (11)	−0.0008 (10)	−0.0003 (11)
C29	0.0227 (12)	0.0211 (12)	0.0195 (11)	−0.0024 (9)	−0.0027 (9)	−0.0008 (9)
C37	0.0188 (12)	0.0294 (13)	0.0233 (12)	−0.0048 (9)	0.0023 (9)	0.0015 (10)
C31	0.0219 (12)	0.0249 (13)	0.0232 (12)	−0.0031 (9)	0.0015 (10)	−0.0004 (10)
C30	0.0217 (12)	0.0240 (12)	0.0198 (12)	−0.0037 (9)	−0.0019 (9)	−0.0003 (9)
C33	0.0224 (12)	0.0285 (13)	0.0194 (11)	−0.0086 (10)	0.0015 (9)	−0.0008 (10)
C28	0.0270 (13)	0.0281 (13)	0.0224 (12)	−0.0068 (10)	0.0011 (10)	−0.0018 (10)
C24	0.0256 (13)	0.0233 (13)	0.0260 (13)	−0.0038 (10)	0.0027 (10)	−0.0040 (10)
C36	0.0221 (12)	0.0308 (14)	0.0224 (12)	−0.0076 (10)	−0.0022 (10)	0.0003 (10)
C23	0.0240 (12)	0.0246 (13)	0.0191 (11)	−0.0046 (10)	0.0021 (9)	−0.0026 (9)
C22	0.0224 (12)	0.0213 (12)	0.0280 (13)	−0.0064 (9)	0.0057 (10)	0.0001 (10)
C35	0.0257 (13)	0.0251 (13)	0.0193 (12)	−0.0082 (10)	0.0033 (9)	−0.0016 (9)
C25	0.0298 (13)	0.0220 (12)	0.0213 (12)	−0.0024 (10)	−0.0038 (10)	−0.0028 (10)
C26	0.0358 (14)	0.0217 (12)	0.0262 (13)	−0.0087 (10)	−0.0052 (11)	−0.0003 (10)
C38	0.0448 (17)	0.0300 (14)	0.0411 (16)	−0.0170 (12)	−0.0111 (13)	−0.0009 (12)
O1	0.0236 (8)	0.0196 (8)	0.0249 (9)	−0.0051 (7)	−0.0048 (7)	0.0009 (7)
O4	0.0236 (9)	0.0231 (9)	0.0421 (11)	−0.0036 (7)	−0.0078 (8)	0.0030 (8)
O2	0.0324 (10)	0.0237 (9)	0.0347 (10)	−0.0108 (8)	0.0047 (8)	−0.0035 (8)
C12	0.0218 (12)	0.0240 (13)	0.0217 (12)	−0.0047 (10)	−0.0051 (9)	−0.0018 (10)
C14	0.0211 (12)	0.0277 (13)	0.0213 (12)	−0.0025 (9)	−0.0006 (9)	−0.0037 (10)
C3	0.0259 (13)	0.0214 (12)	0.0168 (11)	−0.0045 (10)	−0.0002 (9)	−0.0012 (9)
C4	0.0252 (13)	0.0213 (13)	0.0209 (12)	−0.0042 (10)	0.0006 (10)	0.0009 (9)
C11	0.0230 (12)	0.0233 (13)	0.0205 (12)	−0.0045 (10)	−0.0023 (9)	−0.0018 (9)
C8	0.0247 (12)	0.0275 (13)	0.0221 (12)	−0.0045 (10)	−0.0021 (10)	−0.0012 (10)
C7	0.0307 (13)	0.0303 (14)	0.0252 (13)	−0.0131 (11)	0.0000 (10)	−0.0048 (10)
C2	0.0216 (12)	0.0209 (12)	0.0226 (12)	−0.0067 (9)	−0.0016 (9)	−0.0025 (9)
C15	0.0265 (13)	0.0240 (13)	0.0218 (12)	−0.0069 (10)	−0.0024 (10)	−0.0001 (10)
C13	0.0193 (11)	0.0275 (13)	0.0208 (12)	−0.0069 (10)	−0.0008 (9)	−0.0014 (10)
C10	0.0216 (12)	0.0237 (12)	0.0192 (12)	−0.0045 (9)	0.0025 (9)	−0.0007 (9)
C5	0.0253 (13)	0.0234 (13)	0.0203 (12)	−0.0045 (10)	0.0037 (9)	−0.0011 (10)
C9	0.0238 (12)	0.0219 (12)	0.0179 (11)	−0.0049 (10)	0.0030 (9)	−0.0018 (9)
C17	0.0207 (12)	0.0257 (13)	0.0237 (12)	−0.0042 (9)	0.0003 (9)	−0.0043 (10)
C16	0.0227 (12)	0.0295 (13)	0.0262 (13)	−0.0084 (10)	0.0013 (10)	−0.0019 (10)
C6	0.0340 (14)	0.0241 (13)	0.0268 (13)	−0.0100 (10)	0.0030 (10)	−0.0050 (10)
C18	0.0433 (16)	0.0287 (14)	0.0398 (16)	−0.0180 (12)	0.0112 (13)	−0.0049 (12)

Geometric parameters (Å, º)

O22—C35	1.366 (3)	O1—C9	1.366 (3)
O22—C38	1.427 (3)	O1—C2	1.446 (3)
O21—C29	1.366 (3)	O4—C4	1.233 (3)
O21—C22	1.446 (3)	O2—C15	1.365 (3)
O24—C24	1.223 (3)	O2—C18	1.419 (3)
C32—C37	1.397 (4)	C12—C17	1.394 (4)
C32—C33	1.400 (4)	C12—C13	1.408 (3)
C32—C31	1.465 (3)	C12—C11	1.469 (3)
C34—C35	1.387 (4)	C14—C13	1.384 (4)
C34—C33	1.391 (3)	C14—C15	1.386 (4)
C34—H34	0.9500	C14—H14	0.9500
C27—C28	1.388 (4)	C3—C11	1.339 (4)
C27—C26	1.397 (4)	C3—C4	1.488 (3)
C27—H27	0.9500	C3—C2	1.509 (3)
C29—C28	1.382 (4)	C4—C10	1.469 (4)
C29—C30	1.407 (3)	C11—H11	0.9500
C37—C36	1.385 (4)	C8—C9	1.383 (4)
C37—H37	0.9500	C8—C7	1.384 (4)
C31—C23	1.331 (4)	C8—H8	0.9500
C31—H31	0.9500	C7—C6	1.404 (4)
C30—C25	1.404 (3)	C7—H7	0.9500
C30—C24	1.470 (4)	C2—H2A	0.9900
C33—H33	0.9500	C2—H2B	0.9900
C28—H28	0.9500	C15—C16	1.391 (4)
C24—C23	1.494 (3)	C13—H13	0.9500
C36—C35	1.398 (4)	C10—C5	1.404 (3)
C36—H36	0.9500	C10—C9	1.405 (3)
C23—C22	1.514 (3)	C5—C6	1.375 (4)
C22—H22A	0.9900	C5—H5	0.9500
C22—H22B	0.9900	C17—C16	1.393 (4)
C25—C26	1.376 (4)	C17—H17	0.9500
C25—H25	0.9500	C16—H16	0.9500
C26—H26	0.9500	C6—H6	0.9500
C38—H38A	0.9800	C18—H18A	0.9800
C38—H38B	0.9800	C18—H18B	0.9800
C38—H38C	0.9800	C18—H18C	0.9800
C35—O22—C38	118.4 (2)	C9—O1—C2	115.39 (18)
C29—O21—C22	115.55 (18)	C15—O2—C18	118.5 (2)
C37—C32—C33	118.5 (2)	C17—C12—C13	117.9 (2)
C37—C32—C31	118.4 (2)	C17—C12—C11	118.9 (2)
C33—C32—C31	123.1 (2)	C13—C12—C11	123.3 (2)
C35—C34—C33	120.5 (2)	C13—C14—C15	120.2 (2)
C35—C34—H34	119.8	C13—C14—H14	119.9
C33—C34—H34	119.8	C15—C14—H14	119.9
C28—C27—C26	120.6 (2)	C11—C3—C4	119.2 (2)
C28—C27—H27	119.7	C11—C3—C2	125.0 (2)
C26—C27—H27	119.7	C4—C3—C2	115.8 (2)
O21—C29—C28	117.6 (2)	O4—C4—C10	121.8 (2)
O21—C29—C30	121.5 (2)	O4—C4—C3	122.4 (2)
C28—C29—C30	120.9 (2)	C10—C4—C3	115.8 (2)
C36—C37—C32	121.9 (2)	C3—C11—C12	129.4 (2)
C36—C37—H37	119.0	C3—C11—H11	115.3
C32—C37—H37	119.0	C12—C11—H11	115.3
C23—C31—C32	129.6 (2)	C9—C8—C7	119.2 (2)
C23—C31—H31	115.2	C9—C8—H8	120.4
C32—C31—H31	115.2	C7—C8—H8	120.4
C25—C30—C29	118.5 (2)	C8—C7—C6	120.7 (2)
C25—C30—C24	121.2 (2)	C8—C7—H7	119.7
C29—C30—C24	120.1 (2)	C6—C7—H7	119.7
C34—C33—C32	120.1 (2)	O1—C2—C3	111.52 (19)
C34—C33—H33	120.0	O1—C2—H2A	109.3
C32—C33—H33	120.0	C3—C2—H2A	109.3
C29—C28—C27	119.5 (2)	O1—C2—H2B	109.3
C29—C28—H28	120.3	C3—C2—H2B	109.3
C27—C28—H28	120.3	H2A—C2—H2B	108.0
O24—C24—C30	121.4 (2)	O2—C15—C14	115.7 (2)
O24—C24—C23	122.7 (2)	O2—C15—C16	124.0 (2)
C30—C24—C23	115.9 (2)	C14—C15—C16	120.3 (2)
C37—C36—C35	118.7 (2)	C14—C13—C12	120.8 (2)
C37—C36—H36	120.6	C14—C13—H13	119.6
C35—C36—H36	120.6	C12—C13—H13	119.6
C31—C23—C24	119.4 (2)	C5—C10—C9	118.3 (2)
C31—C23—C22	125.5 (2)	C5—C10—C4	121.4 (2)
C24—C23—C22	115.0 (2)	C9—C10—C4	120.1 (2)
O21—C22—C23	111.40 (19)	C6—C5—C10	120.8 (2)
O21—C22—H22A	109.3	C6—C5—H5	119.6
C23—C22—H22A	109.3	C10—C5—H5	119.6
O21—C22—H22B	109.3	O1—C9—C8	117.3 (2)
C23—C22—H22B	109.3	O1—C9—C10	121.3 (2)
H22A—C22—H22B	108.0	C8—C9—C10	121.4 (2)
O22—C35—C34	115.4 (2)	C16—C17—C12	121.7 (2)
O22—C35—C36	124.3 (2)	C16—C17—H17	119.1
C34—C35—C36	120.3 (2)	C12—C17—H17	119.1
C26—C25—C30	120.7 (2)	C15—C16—C17	119.1 (2)
C26—C25—H25	119.6	C15—C16—H16	120.5
C30—C25—H25	119.6	C17—C16—H16	120.5
C25—C26—C27	119.8 (2)	C5—C6—C7	119.7 (2)
C25—C26—H26	120.1	C5—C6—H6	120.2
C27—C26—H26	120.1	C7—C6—H6	120.2
O22—C38—H38A	109.5	O2—C18—H18A	109.5
O22—C38—H38B	109.5	O2—C18—H18B	109.5
H38A—C38—H38B	109.5	H18A—C18—H18B	109.5
O22—C38—H38C	109.5	O2—C18—H18C	109.5
H38A—C38—H38C	109.5	H18A—C18—H18C	109.5
H38B—C38—H38C	109.5	H18B—C18—H18C	109.5
C22—O21—C29—C28	−154.3 (2)	C11—C3—C4—O4	−12.1 (4)
C22—O21—C29—C30	28.9 (3)	C2—C3—C4—O4	171.0 (2)
C33—C32—C37—C36	1.8 (4)	C11—C3—C4—C10	165.8 (2)
C31—C32—C37—C36	179.1 (2)	C2—C3—C4—C10	−11.1 (3)
C37—C32—C31—C23	147.3 (3)	C4—C3—C11—C12	177.8 (2)
C33—C32—C31—C23	−35.7 (4)	C2—C3—C11—C12	−5.6 (4)
O21—C29—C30—C25	178.6 (2)	C17—C12—C11—C3	148.4 (3)
C28—C29—C30—C25	1.8 (3)	C13—C12—C11—C3	−33.6 (4)
O21—C29—C30—C24	3.8 (3)	C9—C8—C7—C6	−0.2 (4)
C28—C29—C30—C24	−172.9 (2)	C9—O1—C2—C3	−52.0 (3)
C35—C34—C33—C32	−0.1 (4)	C11—C3—C2—O1	−134.7 (2)
C37—C32—C33—C34	−1.1 (4)	C4—C3—C2—O1	42.0 (3)
C31—C32—C33—C34	−178.2 (2)	C18—O2—C15—C14	−179.6 (2)
O21—C29—C28—C27	−177.8 (2)	C18—O2—C15—C16	−0.9 (4)
C30—C29—C28—C27	−0.9 (4)	C13—C14—C15—O2	179.1 (2)
C26—C27—C28—C29	−0.7 (4)	C13—C14—C15—C16	0.3 (4)
C25—C30—C24—O24	−6.8 (4)	C15—C14—C13—C12	−0.5 (4)
C29—C30—C24—O24	167.8 (2)	C17—C12—C13—C14	−0.4 (3)
C25—C30—C24—C23	174.9 (2)	C11—C12—C13—C14	−178.4 (2)
C29—C30—C24—C23	−10.5 (3)	O4—C4—C10—C5	−9.7 (4)
C32—C37—C36—C35	−1.3 (4)	C3—C4—C10—C5	172.4 (2)
C32—C31—C23—C24	179.0 (2)	O4—C4—C10—C9	165.8 (2)
C32—C31—C23—C22	−4.1 (4)	C3—C4—C10—C9	−12.1 (3)
O24—C24—C23—C31	−15.2 (4)	C9—C10—C5—C6	−1.1 (3)
C30—C24—C23—C31	163.1 (2)	C4—C10—C5—C6	174.4 (2)
O24—C24—C23—C22	167.7 (2)	C2—O1—C9—C8	−152.8 (2)
C30—C24—C23—C22	−14.0 (3)	C2—O1—C9—C10	30.3 (3)
C29—O21—C22—C23	−52.1 (3)	C7—C8—C9—O1	−178.2 (2)
C31—C23—C22—O21	−132.7 (3)	C7—C8—C9—C10	−1.3 (4)
C24—C23—C22—O21	44.2 (3)	C5—C10—C9—O1	178.7 (2)
C38—O22—C35—C34	−174.6 (2)	C4—C10—C9—O1	3.2 (3)
C38—O22—C35—C36	4.7 (4)	C5—C10—C9—C8	2.0 (3)
C33—C34—C35—O22	180.0 (2)	C4—C10—C9—C8	−173.6 (2)
C33—C34—C35—C36	0.6 (4)	C13—C12—C17—C16	1.5 (4)
C37—C36—C35—O22	−179.2 (2)	C11—C12—C17—C16	179.6 (2)
C37—C36—C35—C34	0.1 (4)	O2—C15—C16—C17	−177.9 (2)
C29—C30—C25—C26	−1.2 (4)	C14—C15—C16—C17	0.8 (4)
C24—C30—C25—C26	173.5 (2)	C12—C17—C16—C15	−1.7 (4)
C30—C25—C26—C27	−0.3 (4)	C10—C5—C6—C7	−0.3 (4)
C28—C27—C26—C25	1.3 (4)	C8—C7—C6—C5	1.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O22^i	0.99	2.51	3.430 (3)	154
C2—H2A···O1^i	0.99	2.58	3.215 (3)	122
C5—H5···O2^ii	0.95	2.55	3.319 (3)	138
C14—H14···O24^iii	0.95	2.54	3.196 (3)	127
C17—H17···O1^iv	0.95	2.45	3.349 (3)	157
C25—H25···O22^v	0.95	2.55	3.275 (3)	133
C33—H33···O4^vi	0.95	2.45	3.381 (3)	166
C37—H37···O21^vii	0.95	2.46	3.330 (3)	153

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z; (iii) −x+1, −y, −z+1; (iv) x−1, y, z; (v) x, y−1, z; (vi) −x, −y+1, −z+1; (vii) x+1, y, z.