The effect of the fused-ring substituent on anthracene chalcones: crystal structural and DFT studies of 1-(anthracen-9-yl)-3-(naphthalen-2-yl)prop-2-en-1-one and 1-(anthracen-9-yl)-3-(pyren-1-yl)prop-2-en-1-one

Two new anthracene chalcones, namely 1-(anthracen-9-yl)-3-(naphthalen-2-yl)prop-2-en-1-one and 1-(anthracen-9-yl)-3-(pyren-1-yl)prop-2-en-1-one, have been successfully synthesized and the effect of the different fused ring substituent system attached to the anthracene chalcone derivative investigated. These compounds show a very narrow band gap due to the large p-conjugated systems, making them promising candidates as optoelectronic materials. Hirshfeld surface analysis has been carried out to show the contribution of inter­molecular contacts and weak inter­actions to supra­molecular stabilization.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.043
• wR factor = 0.114
• Data-to-parameter ratio = 18.1

Structure: II

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.046
• wR factor = 0.137
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -6.278 Report

Alert level G
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.87 mm
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          9 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         25 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: II


Alert level C
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -6.278 Report

Alert level G
PLAT012_ALERT_1_G N.O.K.   _shelx_res_checksum Found in CIF ......     Please Check
PLAT013_ALERT_1_G N.O.K.   _shelx_hkl_checksum Found in CIF ......     Please Check
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.66 mm
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...         15 Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

For both structures, data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008). Program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015) for (I); SHELXL2013 (Sheldrick, 2015) for (II). For both structures, molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

1-(Anthracen-9-yl)-3-(naphthalen-2-yl)prop-2-en-1-one (I)

Crystal data

C27H18O	Dx = 1.288 Mg m^−3
Mr = 358.41	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9963 reflections
a = 13.2129 (10) Å	θ = 2.2–28.1°
b = 11.1224 (8) Å	µ = 0.08 mm^−1
c = 25.1604 (19) Å	T = 100 K
V = 3697.6 (5) Å^3	Plate, yellow
Z = 8	0.87 × 0.43 × 0.20 mm
F(000) = 1504

Data collection

Bruker SMART APEXII Duo CCD area-detector diffractometer	3919 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.067
φ and ω scans	θmax = 28.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→17
Tmin = 0.502, Tmax = 0.746	k = −14→14
96576 measured reflections	l = −33→33
4581 independent 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)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.114	w = 1/[σ^2(Fo^2) + (0.0514P)^2 + 1.843P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
4581 reflections	Δρmax = 0.26 e Å^−3
253 parameters	Δρmin = −0.24 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	0.15754 (7)	0.24179 (8)	0.41888 (4)	0.0269 (2)
C1	0.08186 (8)	0.50963 (10)	0.42203 (4)	0.0177 (2)
C2	0.03476 (9)	0.47889 (11)	0.37257 (4)	0.0211 (2)
H2A	0.0611	0.4144	0.3521	0.025*
C3	−0.04727 (9)	0.54078 (11)	0.35452 (5)	0.0248 (3)
H3A	−0.0768	0.5196	0.3214	0.030*
C4	−0.08930 (9)	0.63697 (11)	0.38471 (5)	0.0253 (3)
H4A	−0.1471	0.6787	0.3719	0.030*
C5	−0.04678 (9)	0.66920 (10)	0.43191 (5)	0.0227 (2)
H5A	−0.0755	0.7333	0.4518	0.027*
C6	0.04037 (8)	0.60806 (10)	0.45192 (4)	0.0185 (2)
C7	0.08565 (9)	0.64129 (10)	0.49988 (4)	0.0196 (2)
H7A	0.0565	0.7043	0.5203	0.024*
C8	0.17270 (9)	0.58413 (10)	0.51852 (4)	0.0186 (2)
C9	0.22208 (9)	0.62058 (11)	0.56649 (4)	0.0226 (2)
H9A	0.1955	0.6861	0.5863	0.027*
C10	0.30638 (10)	0.56309 (11)	0.58417 (5)	0.0251 (3)
H10A	0.3381	0.5886	0.6161	0.030*
C11	0.34727 (10)	0.46500 (11)	0.55501 (5)	0.0258 (3)
H11A	0.4064	0.4256	0.5676	0.031*
C12	0.30260 (9)	0.42693 (11)	0.50918 (5)	0.0223 (2)
H12A	0.3307	0.3608	0.4903	0.027*
C13	0.21408 (8)	0.48513 (10)	0.48908 (4)	0.0179 (2)
C14	0.16655 (8)	0.44797 (10)	0.44189 (4)	0.0172 (2)
C15	0.20387 (9)	0.33672 (10)	0.41364 (4)	0.0189 (2)
C16	0.29376 (9)	0.34358 (11)	0.37952 (4)	0.0211 (2)
H16A	0.3175	0.2724	0.3628	0.025*
C17	0.34341 (8)	0.44712 (11)	0.37123 (4)	0.0195 (2)
H17A	0.3184	0.5158	0.3894	0.023*
C18	0.43188 (8)	0.46569 (10)	0.33722 (4)	0.0195 (2)
C19	0.47087 (9)	0.37481 (11)	0.30286 (4)	0.0217 (2)
H19A	0.4391	0.2982	0.3015	0.026*
C20	0.55373 (9)	0.39751 (11)	0.27192 (4)	0.0223 (2)
H20A	0.5775	0.3369	0.2485	0.027*
C21	0.60512 (9)	0.50964 (11)	0.27401 (4)	0.0202 (2)
C22	0.69383 (9)	0.53418 (11)	0.24427 (5)	0.0240 (3)
H22A	0.7192	0.4754	0.2204	0.029*
C23	0.74340 (10)	0.64171 (12)	0.24957 (5)	0.0268 (3)
H23A	0.8035	0.6561	0.2298	0.032*
C24	0.70585 (9)	0.73139 (12)	0.28419 (5)	0.0255 (3)
H24A	0.7410	0.8055	0.2878	0.031*
C25	0.61895 (9)	0.71144 (11)	0.31242 (4)	0.0222 (2)
H25A	0.5932	0.7728	0.3349	0.027*
C26	0.56693 (8)	0.60044 (10)	0.30848 (4)	0.0194 (2)
C27	0.47889 (8)	0.57612 (10)	0.33878 (4)	0.0193 (2)
H27A	0.4516	0.6376	0.3607	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0302 (5)	0.0210 (4)	0.0294 (5)	−0.0044 (3)	−0.0006 (4)	−0.0043 (3)
C1	0.0196 (5)	0.0191 (5)	0.0143 (5)	−0.0023 (4)	0.0018 (4)	0.0014 (4)
C2	0.0232 (5)	0.0243 (6)	0.0157 (5)	−0.0014 (4)	−0.0002 (4)	−0.0006 (4)
C3	0.0256 (6)	0.0299 (6)	0.0191 (5)	−0.0017 (5)	−0.0036 (4)	0.0015 (5)
C4	0.0225 (6)	0.0266 (6)	0.0269 (6)	0.0021 (5)	−0.0018 (5)	0.0052 (5)
C5	0.0233 (6)	0.0197 (5)	0.0251 (6)	0.0008 (4)	0.0031 (4)	0.0025 (4)
C6	0.0196 (5)	0.0182 (5)	0.0176 (5)	−0.0022 (4)	0.0030 (4)	0.0022 (4)
C7	0.0240 (5)	0.0171 (5)	0.0177 (5)	−0.0021 (4)	0.0045 (4)	−0.0009 (4)
C8	0.0239 (5)	0.0178 (5)	0.0141 (5)	−0.0035 (4)	0.0021 (4)	0.0004 (4)
C9	0.0319 (6)	0.0204 (5)	0.0154 (5)	−0.0033 (5)	0.0017 (4)	−0.0022 (4)
C10	0.0357 (7)	0.0247 (6)	0.0150 (5)	−0.0058 (5)	−0.0050 (5)	−0.0009 (4)
C11	0.0312 (6)	0.0253 (6)	0.0209 (6)	0.0015 (5)	−0.0078 (5)	0.0007 (5)
C12	0.0278 (6)	0.0203 (5)	0.0188 (5)	0.0020 (4)	−0.0032 (4)	−0.0009 (4)
C13	0.0220 (5)	0.0174 (5)	0.0142 (5)	−0.0024 (4)	0.0002 (4)	0.0003 (4)
C14	0.0205 (5)	0.0170 (5)	0.0141 (5)	−0.0019 (4)	0.0013 (4)	0.0004 (4)
C15	0.0221 (5)	0.0201 (5)	0.0146 (5)	0.0006 (4)	−0.0045 (4)	−0.0020 (4)
C16	0.0243 (6)	0.0226 (5)	0.0163 (5)	0.0037 (4)	−0.0024 (4)	−0.0039 (4)
C17	0.0211 (5)	0.0240 (5)	0.0134 (5)	0.0042 (4)	−0.0028 (4)	−0.0019 (4)
C18	0.0198 (5)	0.0249 (6)	0.0137 (5)	0.0036 (4)	−0.0028 (4)	−0.0011 (4)
C19	0.0243 (5)	0.0244 (6)	0.0165 (5)	0.0016 (4)	−0.0028 (4)	−0.0037 (4)
C20	0.0258 (6)	0.0266 (6)	0.0144 (5)	0.0051 (5)	−0.0012 (4)	−0.0046 (4)
C21	0.0223 (5)	0.0266 (6)	0.0118 (5)	0.0037 (4)	−0.0025 (4)	−0.0002 (4)
C22	0.0260 (6)	0.0307 (6)	0.0154 (5)	0.0046 (5)	0.0022 (4)	−0.0013 (4)
C23	0.0250 (6)	0.0349 (6)	0.0205 (5)	0.0015 (5)	0.0030 (5)	0.0037 (5)
C24	0.0267 (6)	0.0274 (6)	0.0223 (6)	−0.0008 (5)	−0.0015 (5)	0.0036 (5)
C25	0.0258 (6)	0.0235 (6)	0.0174 (5)	0.0034 (4)	−0.0022 (4)	−0.0003 (4)
C26	0.0215 (5)	0.0248 (6)	0.0120 (5)	0.0044 (4)	−0.0030 (4)	0.0006 (4)
C27	0.0209 (5)	0.0239 (5)	0.0132 (5)	0.0050 (4)	−0.0020 (4)	−0.0015 (4)

Geometric parameters (Å, º)

O1—C15	1.2275 (14)	C13—C14	1.4052 (15)
C1—C14	1.4044 (15)	C14—C15	1.5097 (15)
C1—C2	1.4328 (15)	C15—C16	1.4675 (16)
C1—C6	1.4370 (15)	C16—C17	1.3416 (17)
C2—C3	1.3619 (17)	C16—H16A	0.9500
C2—H2A	0.9500	C17—C18	1.4634 (16)
C3—C4	1.4247 (18)	C17—H17A	0.9500
C3—H3A	0.9500	C18—C27	1.3769 (16)
C4—C5	1.3618 (17)	C18—C19	1.4265 (15)
C4—H4A	0.9500	C19—C20	1.3668 (17)
C5—C6	1.4290 (16)	C19—H19A	0.9500
C5—H5A	0.9500	C20—C21	1.4210 (17)
C6—C7	1.3965 (16)	C20—H20A	0.9500
C7—C8	1.3954 (16)	C21—C22	1.4171 (16)
C7—H7A	0.9500	C21—C26	1.4237 (15)
C8—C9	1.4306 (15)	C22—C23	1.3701 (18)
C8—C13	1.4353 (15)	C22—H22A	0.9500
C9—C10	1.3593 (18)	C23—C24	1.4142 (18)
C9—H9A	0.9500	C23—H23A	0.9500
C10—C11	1.4214 (17)	C24—C25	1.3682 (17)
C10—H10A	0.9500	C24—H24A	0.9500
C11—C12	1.3629 (16)	C25—C26	1.4165 (17)
C11—H11A	0.9500	C25—H25A	0.9500
C12—C13	1.4292 (16)	C26—C27	1.4168 (16)
C12—H12A	0.9500	C27—H27A	0.9500
C14—C1—C2	122.59 (10)	C13—C14—C15	119.53 (10)
C14—C1—C6	119.32 (10)	O1—C15—C16	120.73 (10)
C2—C1—C6	118.08 (10)	O1—C15—C14	119.45 (10)
C3—C2—C1	120.97 (11)	C16—C15—C14	119.81 (10)
C3—C2—H2A	119.5	C17—C16—C15	122.09 (10)
C1—C2—H2A	119.5	C17—C16—H16A	119.0
C2—C3—C4	120.80 (11)	C15—C16—H16A	119.0
C2—C3—H3A	119.6	C16—C17—C18	127.06 (11)
C4—C3—H3A	119.6	C16—C17—H17A	116.5
C5—C4—C3	120.12 (11)	C18—C17—H17A	116.5
C5—C4—H4A	119.9	C27—C18—C19	119.10 (10)
C3—C4—H4A	119.9	C27—C18—C17	118.01 (10)
C4—C5—C6	120.96 (11)	C19—C18—C17	122.88 (11)
C4—C5—H5A	119.5	C20—C19—C18	120.24 (11)
C6—C5—H5A	119.5	C20—C19—H19A	119.9
C7—C6—C5	121.58 (10)	C18—C19—H19A	119.9
C7—C6—C1	119.37 (10)	C19—C20—C21	121.59 (11)
C5—C6—C1	119.05 (10)	C19—C20—H20A	119.2
C8—C7—C6	121.54 (10)	C21—C20—H20A	119.2
C8—C7—H7A	119.2	C22—C21—C20	123.01 (11)
C6—C7—H7A	119.2	C22—C21—C26	118.57 (11)
C7—C8—C9	122.03 (10)	C20—C21—C26	118.41 (10)
C7—C8—C13	119.34 (10)	C23—C22—C21	120.81 (11)
C9—C8—C13	118.63 (10)	C23—C22—H22A	119.6
C10—C9—C8	121.10 (11)	C21—C22—H22A	119.6
C10—C9—H9A	119.5	C22—C23—C24	120.53 (12)
C8—C9—H9A	119.5	C22—C23—H23A	119.7
C9—C10—C11	120.24 (11)	C24—C23—H23A	119.7
C9—C10—H10A	119.9	C25—C24—C23	119.98 (12)
C11—C10—H10A	119.9	C25—C24—H24A	120.0
C12—C11—C10	120.70 (11)	C23—C24—H24A	120.0
C12—C11—H11A	119.6	C24—C25—C26	120.82 (11)
C10—C11—H11A	119.6	C24—C25—H25A	119.6
C11—C12—C13	120.87 (11)	C26—C25—H25A	119.6
C11—C12—H12A	119.6	C25—C26—C27	121.82 (10)
C13—C12—H12A	119.6	C25—C26—C21	119.27 (10)
C14—C13—C12	122.10 (10)	C27—C26—C21	118.90 (11)
C14—C13—C8	119.44 (10)	C18—C27—C26	121.70 (10)
C12—C13—C8	118.46 (10)	C18—C27—H27A	119.2
C1—C14—C13	120.87 (10)	C26—C27—H27A	119.2
C1—C14—C15	119.53 (9)
C14—C1—C2—C3	−179.94 (11)	C12—C13—C14—C15	5.41 (16)
C6—C1—C2—C3	−0.31 (16)	C8—C13—C14—C15	−174.20 (10)
C1—C2—C3—C4	−0.79 (18)	C1—C14—C15—O1	−76.15 (14)
C2—C3—C4—C5	0.86 (18)	C13—C14—C15—O1	100.87 (13)
C3—C4—C5—C6	0.21 (18)	C1—C14—C15—C16	102.72 (12)
C4—C5—C6—C7	179.05 (11)	C13—C14—C15—C16	−80.26 (13)
C4—C5—C6—C1	−1.30 (17)	O1—C15—C16—C17	177.11 (11)
C14—C1—C6—C7	0.64 (16)	C14—C15—C16—C17	−1.74 (16)
C2—C1—C6—C7	−179.01 (10)	C15—C16—C17—C18	−178.36 (10)
C14—C1—C6—C5	−179.02 (10)	C16—C17—C18—C27	−172.68 (11)
C2—C1—C6—C5	1.33 (15)	C16—C17—C18—C19	7.35 (18)
C5—C6—C7—C8	−177.86 (10)	C27—C18—C19—C20	−0.07 (16)
C1—C6—C7—C8	2.49 (16)	C17—C18—C19—C20	179.89 (10)
C6—C7—C8—C9	177.43 (10)	C18—C19—C20—C21	1.88 (17)
C6—C7—C8—C13	−2.98 (16)	C19—C20—C21—C22	177.08 (11)
C7—C8—C9—C10	179.50 (11)	C19—C20—C21—C26	−1.46 (16)
C13—C8—C9—C10	−0.10 (17)	C20—C21—C22—C23	−176.84 (11)
C8—C9—C10—C11	0.05 (18)	C26—C21—C22—C23	1.70 (17)
C9—C10—C11—C12	−0.25 (19)	C21—C22—C23—C24	−1.17 (18)
C10—C11—C12—C13	0.48 (19)	C22—C23—C24—C25	−0.48 (18)
C11—C12—C13—C14	179.87 (11)	C23—C24—C25—C26	1.55 (17)
C11—C12—C13—C8	−0.51 (17)	C24—C25—C26—C27	177.67 (11)
C7—C8—C13—C14	0.33 (16)	C24—C25—C26—C21	−0.98 (16)
C9—C8—C13—C14	179.94 (10)	C22—C21—C26—C25	−0.63 (16)
C7—C8—C13—C12	−179.29 (10)	C20—C21—C26—C25	177.98 (10)
C9—C8—C13—C12	0.32 (16)	C22—C21—C26—C27	−179.32 (10)
C2—C1—C14—C13	176.37 (10)	C20—C21—C26—C27	−0.72 (15)
C6—C1—C14—C13	−3.26 (16)	C19—C18—C27—C26	−2.15 (16)
C2—C1—C14—C15	−6.65 (16)	C17—C18—C27—C26	177.88 (10)
C6—C1—C14—C15	173.72 (10)	C25—C26—C27—C18	−176.12 (10)
C12—C13—C14—C1	−177.61 (10)	C21—C26—C27—C18	2.54 (16)
C8—C13—C14—C1	2.78 (16)

Hydrogen-bond geometry (Å, º)

Cg4 is the centroid of the C18–C20/C25–C27 ring

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27A···O1^i	0.95	2.36	3.2721 (14)	161
C10—H10A···Cg4^ii	0.95	2.85	3.6610 (14)	142

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

1-(Anthracen-9-yl)-3-(pyren-1-yl)prop-2-en-1-one (II)

Crystal data

C33H20O	F(000) = 904
Mr = 432.49	Dx = 1.285 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.118 (5) Å	Cell parameters from 5604 reflections
b = 12.310 (4) Å	θ = 2.5–23.7°
c = 11.152 (3) Å	µ = 0.08 mm^−1
β = 107.929 (5)°	T = 296 K
V = 2235.8 (12) Å^3	Plate, yellow
Z = 4	0.66 × 0.66 × 0.26 mm

Data collection

Bruker SMART APEXII Duo CCD area-detector diffractometer	2739 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
φ and ω scans	θmax = 26.0°, θmin = 1.3°
Absorption correction: multi-scan SADABS 2014/5	h = −21→21
Tmin = 0.700, Tmax = 0.927	k = −15→15
39809 measured reflections	l = −13→13
4394 independent 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)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.137	w = 1/[σ^2(Fo^2) + (0.0446P)^2 + 0.5972P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
4394 reflections	Δρmax = 0.15 e Å^−3
307 parameters	Δρmin = −0.14 e Å^−3

Special details

Experimental. The following wavelength and cell were deduced by SADABS from the direction cosines etc. They are given here for emergency use only: CELL 0.71104 11.238 12.388 17.234 90.027 107.859 90.073

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	0.17677 (10)	0.46286 (15)	0.87794 (14)	0.0885 (5)
C1	0.14507 (12)	0.62079 (18)	0.6345 (2)	0.0624 (5)
C2	0.17465 (15)	0.70424 (19)	0.7246 (2)	0.0779 (7)
H2A	0.2030	0.6861	0.8076	0.093*
C3	0.16206 (18)	0.8103 (2)	0.6912 (3)	0.0982 (9)
H3A	0.1814	0.8642	0.7515	0.118*
C4	0.12019 (19)	0.8391 (3)	0.5668 (4)	0.1063 (10)
H4A	0.1126	0.9122	0.5449	0.128*
C5	0.09075 (17)	0.7625 (3)	0.4782 (3)	0.0944 (8)
H5A	0.0626	0.7833	0.3961	0.113*
C6	0.10194 (13)	0.6505 (2)	0.5082 (2)	0.0713 (6)
C7	0.07398 (13)	0.5692 (2)	0.4191 (2)	0.0783 (7)
H7A	0.0454	0.5887	0.3367	0.094*
C8	0.08713 (12)	0.4605 (2)	0.4484 (2)	0.0690 (6)
C9	0.06052 (14)	0.3764 (3)	0.3561 (2)	0.0871 (8)
H9A	0.0325	0.3946	0.2730	0.105*
C10	0.07563 (16)	0.2710 (3)	0.3882 (3)	0.0925 (8)
H10A	0.0582	0.2174	0.3270	0.111*
C11	0.11715 (15)	0.2417 (2)	0.5122 (3)	0.0832 (7)
H11A	0.1266	0.1687	0.5329	0.100*
C12	0.14376 (13)	0.31760 (19)	0.6026 (2)	0.0698 (6)
H12A	0.1715	0.2962	0.6847	0.084*
C13	0.13005 (11)	0.42991 (18)	0.57442 (19)	0.0593 (5)
C14	0.15845 (12)	0.51091 (17)	0.66534 (18)	0.0574 (5)
C15	0.20900 (13)	0.47913 (16)	0.79620 (19)	0.0625 (5)
C16	0.29722 (13)	0.47072 (17)	0.82128 (18)	0.0650 (6)
H16A	0.3292	0.4442	0.8990	0.078*
C17	0.33365 (12)	0.49963 (16)	0.73682 (18)	0.0573 (5)
H17A	0.2989	0.5221	0.6590	0.069*
C18	0.42074 (12)	0.50067 (15)	0.75046 (16)	0.0531 (5)
C19	0.47586 (13)	0.44278 (16)	0.84749 (18)	0.0631 (5)
H19A	0.4561	0.4033	0.9031	0.076*
C20	0.55833 (13)	0.44252 (17)	0.86316 (18)	0.0649 (5)
H20A	0.5933	0.4026	0.9287	0.078*
C21	0.59063 (12)	0.50066 (16)	0.78327 (17)	0.0551 (5)
C22	0.67696 (13)	0.50448 (18)	0.7997 (2)	0.0680 (6)
H22A	0.7130	0.4666	0.8661	0.082*
C23	0.70663 (13)	0.56110 (19)	0.7218 (2)	0.0705 (6)
H23A	0.7630	0.5620	0.7354	0.085*
C24	0.65461 (13)	0.62047 (16)	0.61809 (19)	0.0594 (5)
C25	0.68439 (15)	0.67865 (19)	0.5348 (2)	0.0749 (6)
H25A	0.7406	0.6805	0.5469	0.090*
C26	0.63215 (17)	0.73339 (18)	0.4350 (2)	0.0788 (7)
H26A	0.6533	0.7712	0.3798	0.095*
C27	0.54903 (15)	0.73297 (16)	0.4157 (2)	0.0691 (6)
H27A	0.5145	0.7708	0.3478	0.083*
C28	0.51601 (13)	0.67643 (15)	0.49669 (17)	0.0549 (5)
C29	0.43069 (13)	0.67432 (15)	0.48102 (18)	0.0591 (5)
H29A	0.3951	0.7117	0.4137	0.071*
C30	0.39964 (12)	0.61986 (15)	0.56071 (17)	0.0557 (5)
H30A	0.3433	0.6217	0.5478	0.067*
C31	0.45105 (11)	0.55896 (14)	0.66509 (15)	0.0475 (4)
C32	0.53673 (11)	0.55946 (14)	0.68243 (16)	0.0486 (4)
C33	0.56895 (11)	0.61898 (14)	0.59947 (16)	0.0505 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0916 (12)	0.1139 (14)	0.0734 (10)	−0.0170 (10)	0.0451 (9)	0.0037 (9)
C1	0.0527 (12)	0.0709 (14)	0.0726 (13)	−0.0068 (11)	0.0327 (10)	−0.0003 (11)
C2	0.0823 (17)	0.0696 (15)	0.0930 (17)	−0.0158 (13)	0.0435 (13)	−0.0055 (13)
C3	0.110 (2)	0.0706 (18)	0.135 (3)	−0.0190 (15)	0.069 (2)	−0.0066 (17)
C4	0.106 (2)	0.0743 (19)	0.160 (3)	0.0064 (17)	0.072 (2)	0.030 (2)
C5	0.0829 (19)	0.096 (2)	0.114 (2)	0.0105 (16)	0.0439 (16)	0.0293 (18)
C6	0.0562 (13)	0.0819 (17)	0.0833 (15)	0.0032 (12)	0.0324 (12)	0.0153 (13)
C7	0.0541 (14)	0.111 (2)	0.0690 (14)	0.0022 (13)	0.0172 (11)	0.0113 (14)
C8	0.0466 (12)	0.0953 (18)	0.0670 (13)	−0.0059 (12)	0.0202 (10)	−0.0061 (12)
C9	0.0581 (15)	0.131 (2)	0.0695 (15)	−0.0141 (16)	0.0161 (11)	−0.0231 (16)
C10	0.0708 (17)	0.112 (2)	0.100 (2)	−0.0216 (16)	0.0331 (15)	−0.0421 (18)
C11	0.0720 (16)	0.0844 (17)	0.1006 (19)	−0.0136 (13)	0.0374 (15)	−0.0248 (15)
C12	0.0616 (14)	0.0754 (15)	0.0781 (14)	−0.0078 (11)	0.0300 (11)	−0.0104 (12)
C13	0.0446 (11)	0.0735 (14)	0.0654 (12)	−0.0071 (10)	0.0255 (9)	−0.0064 (10)
C14	0.0495 (11)	0.0668 (13)	0.0629 (12)	−0.0077 (10)	0.0276 (9)	−0.0016 (10)
C15	0.0711 (14)	0.0635 (13)	0.0598 (12)	−0.0152 (11)	0.0303 (11)	−0.0039 (10)
C16	0.0643 (14)	0.0771 (14)	0.0522 (11)	−0.0100 (11)	0.0159 (10)	0.0015 (10)
C17	0.0571 (12)	0.0611 (12)	0.0532 (11)	−0.0047 (10)	0.0160 (9)	0.0007 (9)
C18	0.0548 (12)	0.0535 (11)	0.0490 (10)	−0.0017 (9)	0.0129 (9)	−0.0009 (8)
C19	0.0672 (14)	0.0651 (13)	0.0554 (11)	−0.0044 (11)	0.0167 (10)	0.0087 (10)
C20	0.0639 (14)	0.0671 (13)	0.0565 (11)	0.0091 (11)	0.0081 (10)	0.0110 (10)
C21	0.0534 (12)	0.0560 (11)	0.0520 (10)	0.0032 (9)	0.0104 (9)	−0.0042 (9)
C22	0.0557 (13)	0.0738 (14)	0.0685 (13)	0.0099 (11)	0.0104 (10)	−0.0021 (11)
C23	0.0509 (12)	0.0775 (15)	0.0825 (15)	0.0010 (11)	0.0197 (11)	−0.0111 (12)
C24	0.0591 (13)	0.0544 (12)	0.0693 (12)	−0.0039 (10)	0.0264 (10)	−0.0130 (10)
C25	0.0730 (15)	0.0687 (14)	0.0951 (17)	−0.0120 (12)	0.0434 (14)	−0.0130 (13)
C26	0.099 (2)	0.0656 (15)	0.0888 (17)	−0.0090 (13)	0.0529 (15)	0.0009 (12)
C27	0.0876 (17)	0.0551 (12)	0.0725 (14)	−0.0002 (12)	0.0365 (12)	0.0043 (10)
C28	0.0675 (14)	0.0437 (10)	0.0567 (11)	−0.0014 (9)	0.0241 (10)	−0.0035 (8)
C29	0.0682 (14)	0.0512 (11)	0.0558 (11)	0.0073 (10)	0.0159 (10)	0.0065 (9)
C30	0.0521 (11)	0.0541 (11)	0.0592 (11)	0.0040 (9)	0.0145 (9)	0.0010 (9)
C31	0.0522 (11)	0.0435 (10)	0.0455 (9)	0.0000 (8)	0.0131 (8)	−0.0034 (8)
C32	0.0519 (11)	0.0445 (10)	0.0483 (10)	0.0008 (8)	0.0136 (8)	−0.0062 (8)
C33	0.0585 (12)	0.0422 (10)	0.0541 (10)	−0.0023 (9)	0.0222 (9)	−0.0090 (8)

Geometric parameters (Å, º)

O1—C15	1.219 (2)	C17—C18	1.451 (3)
C1—C14	1.397 (3)	C17—H17A	0.9300
C1—C2	1.417 (3)	C18—C19	1.393 (3)
C1—C6	1.423 (3)	C18—C31	1.412 (2)
C2—C3	1.356 (3)	C19—C20	1.368 (3)
C2—H2A	0.9300	C19—H19A	0.9300
C3—C4	1.397 (4)	C20—C21	1.384 (3)
C3—H3A	0.9300	C20—H20A	0.9300
C4—C5	1.346 (4)	C21—C32	1.415 (2)
C4—H4A	0.9300	C21—C22	1.433 (3)
C5—C6	1.417 (3)	C22—C23	1.330 (3)
C5—H5A	0.9300	C22—H22A	0.9300
C6—C7	1.388 (3)	C23—C24	1.425 (3)
C7—C8	1.379 (3)	C23—H23A	0.9300
C7—H7A	0.9300	C24—C25	1.388 (3)
C8—C13	1.422 (3)	C24—C33	1.416 (3)
C8—C9	1.432 (3)	C25—C26	1.371 (3)
C9—C10	1.349 (4)	C25—H25A	0.9300
C9—H9A	0.9300	C26—C27	1.372 (3)
C10—C11	1.394 (4)	C26—H26A	0.9300
C10—H10A	0.9300	C27—C28	1.391 (3)
C11—C12	1.347 (3)	C27—H27A	0.9300
C11—H11A	0.9300	C28—C33	1.413 (3)
C12—C13	1.421 (3)	C28—C29	1.417 (3)
C12—H12A	0.9300	C29—C30	1.346 (3)
C13—C14	1.398 (3)	C29—H29A	0.9300
C14—C15	1.501 (3)	C30—C31	1.436 (2)
C15—C16	1.452 (3)	C30—H30A	0.9300
C16—C17	1.328 (3)	C31—C32	1.419 (2)
C16—H16A	0.9300	C32—C33	1.418 (2)
C14—C1—C2	122.1 (2)	C18—C17—H17A	115.9
C14—C1—C6	119.2 (2)	C19—C18—C31	118.81 (18)
C2—C1—C6	118.6 (2)	C19—C18—C17	120.35 (17)
C3—C2—C1	120.7 (3)	C31—C18—C17	120.83 (17)
C3—C2—H2A	119.7	C20—C19—C18	121.75 (19)
C1—C2—H2A	119.7	C20—C19—H19A	119.1
C2—C3—C4	120.5 (3)	C18—C19—H19A	119.1
C2—C3—H3A	119.7	C19—C20—C21	121.17 (18)
C4—C3—H3A	119.7	C19—C20—H20A	119.4
C5—C4—C3	120.8 (3)	C21—C20—H20A	119.4
C5—C4—H4A	119.6	C20—C21—C32	118.97 (18)
C3—C4—H4A	119.6	C20—C21—C22	122.38 (19)
C4—C5—C6	121.1 (3)	C32—C21—C22	118.65 (18)
C4—C5—H5A	119.5	C23—C22—C21	121.3 (2)
C6—C5—H5A	119.5	C23—C22—H22A	119.3
C7—C6—C5	122.7 (2)	C21—C22—H22A	119.3
C7—C6—C1	118.9 (2)	C22—C23—C24	122.0 (2)
C5—C6—C1	118.3 (2)	C22—C23—H23A	119.0
C8—C7—C6	122.3 (2)	C24—C23—H23A	119.0
C8—C7—H7A	118.8	C25—C24—C33	119.0 (2)
C6—C7—H7A	118.8	C25—C24—C23	122.8 (2)
C7—C8—C13	119.2 (2)	C33—C24—C23	118.20 (18)
C7—C8—C9	122.6 (2)	C26—C25—C24	121.0 (2)
C13—C8—C9	118.2 (2)	C26—C25—H25A	119.5
C10—C9—C8	120.8 (2)	C24—C25—H25A	119.5
C10—C9—H9A	119.6	C25—C26—C27	120.8 (2)
C8—C9—H9A	119.6	C25—C26—H26A	119.6
C9—C10—C11	120.6 (2)	C27—C26—H26A	119.6
C9—C10—H10A	119.7	C26—C27—C28	120.6 (2)
C11—C10—H10A	119.7	C26—C27—H27A	119.7
C12—C11—C10	121.0 (3)	C28—C27—H27A	119.7
C12—C11—H11A	119.5	C27—C28—C33	119.35 (19)
C10—C11—H11A	119.5	C27—C28—C29	122.59 (19)
C11—C12—C13	120.9 (2)	C33—C28—C29	118.05 (17)
C11—C12—H12A	119.5	C30—C29—C28	121.96 (18)
C13—C12—H12A	119.5	C30—C29—H29A	119.0
C14—C13—C12	122.4 (2)	C28—C29—H29A	119.0
C14—C13—C8	119.1 (2)	C29—C30—C31	121.82 (19)
C12—C13—C8	118.5 (2)	C29—C30—H30A	119.1
C1—C14—C13	121.20 (19)	C31—C30—H30A	119.1
C1—C14—C15	119.54 (18)	C18—C31—C32	119.28 (16)
C13—C14—C15	119.13 (19)	C18—C31—C30	123.45 (17)
O1—C15—C16	121.8 (2)	C32—C31—C30	117.26 (16)
O1—C15—C14	120.8 (2)	C21—C32—C33	119.57 (17)
C16—C15—C14	117.37 (16)	C21—C32—C31	120.00 (17)
C17—C16—C15	122.12 (19)	C33—C32—C31	120.43 (16)
C17—C16—H16A	118.9	C28—C33—C24	119.28 (17)
C15—C16—H16A	118.9	C28—C33—C32	120.46 (17)
C16—C17—C18	128.28 (19)	C24—C33—C32	120.26 (17)
C16—C17—H17A	115.9
C14—C1—C2—C3	178.7 (2)	C17—C18—C19—C20	−179.72 (19)
C6—C1—C2—C3	0.1 (3)	C18—C19—C20—C21	0.4 (3)
C1—C2—C3—C4	−0.5 (4)	C19—C20—C21—C32	−1.2 (3)
C2—C3—C4—C5	0.8 (4)	C19—C20—C21—C22	178.09 (19)
C3—C4—C5—C6	−0.6 (4)	C20—C21—C22—C23	−179.9 (2)
C4—C5—C6—C7	−178.7 (2)	C32—C21—C22—C23	−0.6 (3)
C4—C5—C6—C1	0.1 (4)	C21—C22—C23—C24	−0.2 (3)
C14—C1—C6—C7	0.3 (3)	C22—C23—C24—C25	−179.0 (2)
C2—C1—C6—C7	178.97 (19)	C22—C23—C24—C33	0.6 (3)
C14—C1—C6—C5	−178.49 (19)	C33—C24—C25—C26	−0.6 (3)
C2—C1—C6—C5	0.1 (3)	C23—C24—C25—C26	179.0 (2)
C5—C6—C7—C8	178.2 (2)	C24—C25—C26—C27	0.7 (3)
C1—C6—C7—C8	−0.6 (3)	C25—C26—C27—C28	−0.3 (3)
C6—C7—C8—C13	0.7 (3)	C26—C27—C28—C33	−0.1 (3)
C6—C7—C8—C9	−178.1 (2)	C26—C27—C28—C29	179.52 (19)
C7—C8—C9—C10	179.0 (2)	C27—C28—C29—C30	−179.52 (19)
C13—C8—C9—C10	0.2 (3)	C33—C28—C29—C30	0.1 (3)
C8—C9—C10—C11	0.3 (4)	C28—C29—C30—C31	−1.2 (3)
C9—C10—C11—C12	−0.6 (4)	C19—C18—C31—C32	−1.7 (3)
C10—C11—C12—C13	0.2 (3)	C17—C18—C31—C32	179.07 (16)
C11—C12—C13—C14	−178.52 (19)	C19—C18—C31—C30	179.00 (17)
C11—C12—C13—C8	0.3 (3)	C17—C18—C31—C30	−0.2 (3)
C7—C8—C13—C14	−0.5 (3)	C29—C30—C31—C18	−179.86 (18)
C9—C8—C13—C14	178.36 (18)	C29—C30—C31—C32	0.9 (3)
C7—C8—C13—C12	−179.37 (19)	C20—C21—C32—C33	−179.70 (17)
C9—C8—C13—C12	−0.5 (3)	C22—C21—C32—C33	1.0 (3)
C2—C1—C14—C13	−178.78 (18)	C20—C21—C32—C31	0.5 (3)
C6—C1—C14—C13	−0.2 (3)	C22—C21—C32—C31	−178.81 (17)
C2—C1—C14—C15	−2.9 (3)	C18—C31—C32—C21	0.9 (2)
C6—C1—C14—C15	175.70 (17)	C30—C31—C32—C21	−179.74 (16)
C12—C13—C14—C1	179.10 (18)	C18—C31—C32—C33	−178.83 (16)
C8—C13—C14—C1	0.3 (3)	C30—C31—C32—C33	0.5 (2)
C12—C13—C14—C15	3.2 (3)	C27—C28—C33—C24	0.2 (3)
C8—C13—C14—C15	−175.62 (17)	C29—C28—C33—C24	−179.45 (16)
C1—C14—C15—O1	91.0 (2)	C27—C28—C33—C32	−179.13 (17)
C13—C14—C15—O1	−93.0 (2)	C29—C28—C33—C32	1.2 (2)
C1—C14—C15—C16	−87.9 (2)	C25—C24—C33—C28	0.1 (3)
C13—C14—C15—C16	88.1 (2)	C23—C24—C33—C28	−179.46 (17)
O1—C15—C16—C17	−172.6 (2)	C25—C24—C33—C32	179.47 (17)
C14—C15—C16—C17	6.3 (3)	C23—C24—C33—C32	−0.1 (3)
C15—C16—C17—C18	176.81 (19)	C21—C32—C33—C28	178.70 (16)
C16—C17—C18—C19	17.2 (3)	C31—C32—C33—C28	−1.5 (2)
C16—C17—C18—C31	−163.6 (2)	C21—C32—C33—C24	−0.6 (2)
C31—C18—C19—C20	1.1 (3)	C31—C32—C33—C24	179.16 (16)

Hydrogen-bond geometry (Å, º)

Cg3, Cg4 and Cg5 are the centroids of the C18–C13, C21–C24/C32/C33 and C18–C21/C31/C32 rings

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25A···Cg3^i	0.93	2.82	3.7220 (3)	164
C26—H26A···Cg5^ii	0.93	2.81	3.6050 (3)	144
C27—H27A···Cg4^ii	0.93	2.95	3.6520 (3)	134

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