Hydrogen-bond-driven supramolecular helical assembly of a coumarin-substituted phthalonitrile derivative: synthesis and in vitro anticancer activity against colorectal adenocarcinoma

Phthalonitrile derivatives are generally reported to crystallize in space groups P2₁/c and P1 in the literature. In this study, 7-hydroxy-4,8-dimethyl-3-pentylcoumarin (2) and its phthalonitrile derivative (2d) were crystallized; 2d crystallized in the rare trigonal space group R3. In the phthalonitrile derivative (2d), weak C—H...O hydrogen-bonding interactions promoted the formation of supramolecular double helices, and these supramolecular P and M double helices came together to form a honeycomb-like architectural motif involving one-dimensional tubular channels. In silico molecular-docking studies were performed to support the experimental processes and the results agree with each other. In vitro studies of compounds 2 and 2d were performed in LoVo colorectal adenocarcinoma and CCD18Co healthy human cell lines using flow cytometry. For compounds 2 and 2d, there was a statistically significant increase (p < 0.001) in both early and late apoptosis with respect to the control in a dose-dependent manner.

Computing details

For both structures, program(s) used to solve structure: SHELXT 2014/4 (Sheldrick, 2014); program(s) used to refine structure: SHELXL 2018/3 (Sheldrick, 2015); molecular graphics: Olex2 1.3 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.3 (Dolomanov et al., 2009).

(21gtu143_fs_2_0ma)

Crystal data

C24H22N2O3·[+solvents]	Dx = 1.090 Mg m^−3
Mr = 386.43	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 1475 reflections
a = 49.850 (7) Å	θ = 2.2–18.7°
c = 4.9234 (8) Å	µ = 0.07 mm^−1
V = 10596 (3) Å^3	T = 296 K
Z = 18	Plate, colourless
F(000) = 3672	0.26 × 0.10 × 0.09 mm

Data collection

Bruker APEX-II CCD diffractometer	4177 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	1911 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.061
Detector resolution: 7.9 pixels mm^-1	θmax = 25.1°, θmin = 0.8°
φ and ω scans	h = −37→59
Absorption correction: multi-scan SADABS V2014/4 (Bruker AXS)	k = −58→48
Tmin = 0.393, Tmax = 0.746	l = −5→5
13237 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.110	H-atom parameters constrained
wR(F^2) = 0.378	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max < 0.001
4177 reflections	Δρmax = 0.42 e Å^−3
294 parameters	Δρmin = −0.29 e Å^−3
290 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	Occ. (<1)
O1	0.58536 (9)	0.66105 (8)	0.3036 (7)	0.0821 (12)
O2	0.58900 (11)	0.69363 (9)	−0.0062 (8)	0.1089 (14)
O3	0.58604 (9)	0.59571 (8)	0.9902 (7)	0.0808 (12)
N1	0.50369 (11)	0.46859 (10)	0.6091 (10)	0.0844 (13)
N2	0.55298 (11)	0.44869 (13)	1.1255 (12)	0.0977 (14)
C2	0.57141 (19)	0.67297 (14)	0.1453 (13)	0.0964 (15)
C3	0.53856 (17)	0.66050 (12)	0.1646 (11)	0.0818 (16)
C4	0.52125 (15)	0.63695 (13)	0.3410 (12)	0.0816 (14)
C5	0.52189 (13)	0.60265 (12)	0.7127 (11)	0.0689 (14)
H5	0.500656	0.594028	0.737363	0.083*
C6	0.53775 (13)	0.59287 (11)	0.8681 (10)	0.0668 (14)
H6	0.527597	0.578009	1.002052	0.080*
C7	0.56909 (13)	0.60513 (11)	0.8261 (10)	0.0657 (14)
C8	0.58553 (13)	0.62776 (12)	0.6380 (11)	0.0753 (14)
C9	0.56861 (13)	0.63788 (11)	0.4897 (10)	0.0644 (14)
C10	0.53712 (13)	0.62563 (11)	0.5148 (10)	0.0647 (13)
C11	0.48694 (14)	0.62201 (13)	0.3592 (12)	0.0887 (15)
H11A	0.477776	0.600222	0.324420	0.133*
H11B	0.479675	0.631069	0.227125	0.133*
H11C	0.481238	0.625100	0.537812	0.133*
C12	0.61999 (13)	0.64097 (13)	0.5966 (12)	0.0854 (15)
H12A	0.625059	0.646382	0.408984	0.128*
H12B	0.625534	0.625776	0.647376	0.128*
H12C	0.631219	0.659112	0.707184	0.128*
C13	0.52451 (18)	0.67409 (14)	−0.0226 (12)	0.1049 (18)
H13A	0.504035	0.657885	−0.076726	0.126*
H13B	0.537113	0.681720	−0.185193	0.126*
C14	0.5219 (2)	0.70050 (17)	0.1077 (14)	0.126 (2)
H14A	0.542288	0.718565	0.131277	0.152*	0.558 (8)
H14B	0.511971	0.694280	0.283883	0.152*	0.558 (8)
H14C	0.507546	0.691347	0.257789	0.152*	0.442 (8)
H14D	0.542003	0.714194	0.187978	0.152*	0.442 (8)
C15A	0.5023 (4)	0.7077 (4)	−0.088 (3)	0.150 (3)	0.558 (8)
H15A	0.513550	0.715891	−0.256325	0.180*	0.558 (8)
H15B	0.483237	0.688739	−0.129435	0.180*	0.558 (8)
C15B	0.5127 (5)	0.7208 (4)	−0.035 (5)	0.146 (3)	0.442 (8)
H15C	0.524353	0.728795	−0.202467	0.175*	0.442 (8)
H15D	0.515920	0.738006	0.078702	0.175*	0.442 (8)
C16A	0.4944 (4)	0.7311 (4)	0.032 (3)	0.160 (3)	0.558 (8)
H16A	0.513312	0.749428	0.089104	0.192*	0.558 (8)
H16B	0.481387	0.722201	0.190848	0.192*	0.558 (8)
C16B	0.4788 (5)	0.6995 (5)	−0.092 (5)	0.161 (3)	0.442 (8)
H16C	0.477351	0.687481	−0.252380	0.193*	0.442 (8)
H16D	0.470405	0.685005	0.058122	0.193*	0.442 (8)
C17A	0.4775 (4)	0.7401 (4)	−0.178 (4)	0.162 (3)	0.558 (8)
H17A	0.468536	0.724399	−0.315050	0.243*	0.558 (8)
H17B	0.491941	0.759520	−0.259884	0.243*	0.558 (8)
H17C	0.461411	0.742095	−0.088878	0.243*	0.558 (8)
C17B	0.4579 (5)	0.7127 (5)	−0.136 (5)	0.162 (3)	0.442 (8)
H17D	0.460243	0.720262	−0.318621	0.243*	0.442 (8)
H17E	0.463313	0.729385	−0.010793	0.243*	0.442 (8)
H17F	0.436797	0.696826	−0.106361	0.243*	0.442 (8)
C18	0.57731 (12)	0.56516 (12)	1.0092 (10)	0.0642 (13)
C19	0.55447 (11)	0.54189 (11)	0.8484 (9)	0.0591 (13)
H19	0.543936	0.546658	0.718651	0.071*
C20	0.54772 (11)	0.51164 (11)	0.8850 (9)	0.0576 (12)
C21	0.56434 (11)	0.50469 (12)	1.0723 (10)	0.0641 (13)
C22	0.58679 (12)	0.52859 (13)	1.2290 (11)	0.0716 (15)
H22	0.597553	0.524091	1.358443	0.086*
C23	0.59334 (12)	0.55812 (13)	1.1979 (10)	0.0714 (15)
H23	0.608651	0.573743	1.303467	0.086*
C24	0.52381 (14)	0.48802 (12)	0.7306 (11)	0.0739 (13)
C25	0.55801 (13)	0.47377 (15)	1.1043 (14)	0.0881 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.096 (3)	0.054 (2)	0.066 (2)	0.0140 (19)	0.0202 (19)	0.0061 (18)
O2	0.142 (3)	0.067 (2)	0.086 (3)	0.029 (2)	0.019 (2)	0.0139 (18)
O3	0.086 (2)	0.053 (2)	0.083 (2)	0.0191 (19)	−0.020 (2)	−0.0085 (18)
N1	0.086 (3)	0.058 (2)	0.087 (3)	0.020 (2)	−0.017 (2)	−0.008 (2)
N2	0.072 (2)	0.084 (3)	0.126 (3)	0.031 (3)	0.011 (2)	0.022 (3)
C2	0.135 (3)	0.058 (2)	0.078 (3)	0.035 (2)	0.019 (2)	0.009 (2)
C3	0.128 (4)	0.056 (3)	0.059 (3)	0.043 (3)	−0.009 (3)	−0.012 (2)
C4	0.099 (3)	0.060 (3)	0.079 (3)	0.035 (2)	−0.009 (3)	−0.018 (2)
C5	0.072 (3)	0.051 (3)	0.072 (3)	0.022 (2)	0.012 (3)	−0.009 (2)
C6	0.078 (3)	0.041 (3)	0.069 (3)	0.021 (2)	0.007 (3)	−0.003 (2)
C7	0.074 (3)	0.040 (2)	0.066 (3)	0.017 (2)	−0.005 (3)	−0.012 (2)
C8	0.073 (2)	0.054 (2)	0.074 (3)	0.012 (2)	0.005 (2)	−0.009 (2)
C9	0.077 (3)	0.041 (2)	0.053 (3)	0.013 (2)	0.012 (2)	−0.001 (2)
C10	0.079 (3)	0.044 (2)	0.056 (3)	0.020 (2)	0.005 (2)	−0.007 (2)
C11	0.102 (3)	0.067 (3)	0.086 (3)	0.034 (2)	−0.012 (3)	−0.015 (2)
C12	0.078 (3)	0.062 (2)	0.082 (3)	0.010 (2)	0.005 (2)	−0.007 (2)
C13	0.156 (5)	0.078 (3)	0.080 (4)	0.057 (3)	−0.015 (3)	−0.009 (3)
C14	0.181 (5)	0.100 (4)	0.118 (4)	0.086 (4)	−0.016 (4)	−0.014 (3)
C15A	0.193 (6)	0.120 (5)	0.156 (5)	0.093 (5)	−0.026 (5)	0.001 (5)
C15B	0.195 (6)	0.116 (5)	0.154 (5)	0.099 (4)	−0.020 (5)	−0.004 (5)
C16A	0.197 (6)	0.131 (5)	0.178 (5)	0.102 (4)	−0.027 (5)	−0.001 (5)
C16B	0.197 (6)	0.132 (5)	0.177 (5)	0.100 (5)	−0.027 (5)	0.000 (5)
C17A	0.198 (6)	0.132 (5)	0.180 (5)	0.100 (4)	−0.027 (5)	0.000 (5)
C17B	0.198 (6)	0.132 (5)	0.179 (5)	0.100 (4)	−0.027 (5)	0.000 (5)
C18	0.064 (3)	0.056 (3)	0.054 (3)	0.016 (2)	0.000 (2)	−0.005 (2)
C19	0.061 (3)	0.054 (3)	0.051 (3)	0.020 (2)	−0.001 (2)	−0.007 (2)
C20	0.056 (3)	0.052 (2)	0.054 (3)	0.020 (2)	0.003 (2)	−0.004 (2)
C21	0.051 (3)	0.060 (3)	0.066 (3)	0.017 (2)	0.012 (2)	0.008 (2)
C22	0.054 (3)	0.072 (3)	0.072 (3)	0.020 (3)	−0.004 (2)	0.009 (3)
C23	0.061 (3)	0.067 (3)	0.062 (3)	0.014 (3)	−0.009 (2)	−0.003 (3)
C24	0.078 (3)	0.052 (2)	0.080 (3)	0.023 (2)	−0.015 (2)	−0.007 (2)
C25	0.067 (2)	0.078 (3)	0.118 (3)	0.035 (3)	0.012 (2)	0.024 (3)

Geometric parameters (Å, º)

O1—C2	1.363 (8)	C14—H14D	0.9700
O1—C9	1.381 (6)	C14—C15A	1.540 (8)
O2—C2	1.218 (7)	C14—C15B	1.480 (15)
O3—C7	1.409 (6)	C15A—H15A	0.9700
O3—C18	1.362 (6)	C15A—H15B	0.9700
N1—C24	1.154 (6)	C15A—C16A	1.520 (9)
N2—C25	1.151 (7)	C15B—H15C	0.9700
C2—C3	1.435 (9)	C15B—H15D	0.9700
C3—C4	1.365 (8)	C15B—C16B	1.507 (17)
C3—C13	1.508 (8)	C16A—H16A	0.9700
C4—C10	1.457 (8)	C16A—H16B	0.9700
C4—C11	1.488 (8)	C16A—C17A	1.537 (9)
C5—H5	0.9300	C16B—H16C	0.9700
C5—C6	1.354 (7)	C16B—H16D	0.9700
C5—C10	1.403 (7)	C16B—C17B	1.501 (17)
C6—H6	0.9300	C17A—H17A	0.9600
C6—C7	1.379 (7)	C17A—H17B	0.9600
C7—C8	1.370 (7)	C17A—H17C	0.9600
C8—C9	1.387 (8)	C17B—H17D	0.9600
C8—C12	1.515 (8)	C17B—H17E	0.9600
C9—C10	1.376 (8)	C17B—H17F	0.9600
C11—H11A	0.9600	C18—C19	1.396 (6)
C11—H11B	0.9600	C18—C23	1.381 (7)
C11—H11C	0.9600	C19—H19	0.9300
C12—H12A	0.9600	C19—C20	1.383 (7)
C12—H12B	0.9600	C20—C21	1.394 (7)
C12—H12C	0.9600	C20—C24	1.408 (7)
C13—H13A	0.9700	C21—C22	1.391 (7)
C13—H13B	0.9700	C21—C25	1.419 (8)
C13—C14	1.527 (7)	C22—H22	0.9300
C14—H14A	0.9700	C22—C23	1.348 (7)
C14—H14B	0.9700	C23—H23	0.9300
C14—H14C	0.9700
C2—O1—C9	121.2 (5)	C15B—C14—H14D	106.0
C18—O3—C7	120.2 (4)	C14—C15A—H15A	109.2
O1—C2—C3	119.6 (6)	C14—C15A—H15B	109.2
O2—C2—O1	114.2 (7)	H15A—C15A—H15B	107.9
O2—C2—C3	126.2 (7)	C16A—C15A—C14	112.0 (8)
C2—C3—C13	116.8 (6)	C16A—C15A—H15A	109.2
C4—C3—C2	120.6 (6)	C16A—C15A—H15B	109.2
C4—C3—C13	122.6 (7)	C14—C15B—H15C	111.1
C3—C4—C10	118.3 (6)	C14—C15B—H15D	111.1
C3—C4—C11	122.9 (6)	C14—C15B—C16B	103.2 (13)
C10—C4—C11	118.8 (5)	H15C—C15B—H15D	109.1
C6—C5—H5	119.6	C16B—C15B—H15C	111.1
C6—C5—C10	120.7 (5)	C16B—C15B—H15D	111.1
C10—C5—H5	119.6	C15A—C16A—H16A	109.5
C5—C6—H6	120.3	C15A—C16A—H16B	109.5
C5—C6—C7	119.4 (5)	C15A—C16A—C17A	110.6 (8)
C7—C6—H6	120.3	H16A—C16A—H16B	108.1
C6—C7—O3	120.1 (5)	C17A—C16A—H16A	109.5
C8—C7—O3	116.8 (5)	C17A—C16A—H16B	109.5
C8—C7—C6	123.0 (5)	C15B—C16B—H16C	107.4
C7—C8—C9	115.7 (5)	C15B—C16B—H16D	107.4
C7—C8—C12	122.0 (6)	H16C—C16B—H16D	106.9
C9—C8—C12	122.3 (5)	C17B—C16B—C15B	119.9 (17)
O1—C9—C8	115.5 (5)	C17B—C16B—H16C	107.4
C10—C9—O1	120.6 (5)	C17B—C16B—H16D	107.4
C10—C9—C8	123.9 (5)	C16A—C17A—H17A	109.5
C5—C10—C4	123.2 (5)	C16A—C17A—H17B	109.5
C9—C10—C4	119.7 (5)	C16A—C17A—H17C	109.5
C9—C10—C5	117.2 (5)	H17A—C17A—H17B	109.5
C4—C11—H11A	109.5	H17A—C17A—H17C	109.5
C4—C11—H11B	109.5	H17B—C17A—H17C	109.5
C4—C11—H11C	109.5	C16B—C17B—H17D	109.5
H11A—C11—H11B	109.5	C16B—C17B—H17E	109.5
H11A—C11—H11C	109.5	C16B—C17B—H17F	109.5
H11B—C11—H11C	109.5	H17D—C17B—H17E	109.5
C8—C12—H12A	109.5	H17D—C17B—H17F	109.5
C8—C12—H12B	109.5	H17E—C17B—H17F	109.5
C8—C12—H12C	109.5	O3—C18—C19	124.2 (5)
H12A—C12—H12B	109.5	O3—C18—C23	115.4 (5)
H12A—C12—H12C	109.5	C23—C18—C19	120.4 (5)
H12B—C12—H12C	109.5	C18—C19—H19	120.5
C3—C13—H13A	109.0	C20—C19—C18	119.0 (5)
C3—C13—H13B	109.0	C20—C19—H19	120.5
C3—C13—C14	112.9 (5)	C19—C20—C21	120.4 (5)
H13A—C13—H13B	107.8	C19—C20—C24	119.0 (5)
C14—C13—H13A	109.0	C21—C20—C24	120.6 (5)
C14—C13—H13B	109.0	C20—C21—C25	120.4 (5)
C13—C14—H14A	110.5	C22—C21—C20	118.5 (5)
C13—C14—H14B	110.5	C22—C21—C25	121.1 (5)
C13—C14—H14C	106.0	C21—C22—H22	119.2
C13—C14—H14D	106.0	C23—C22—C21	121.6 (5)
C13—C14—C15A	106.1 (6)	C23—C22—H22	119.2
H14A—C14—H14B	108.7	C18—C23—H23	120.0
H14C—C14—H14D	106.3	C22—C23—C18	120.0 (5)
C15A—C14—H14A	110.5	C22—C23—H23	120.0
C15A—C14—H14B	110.5	N1—C24—C20	178.3 (6)
C15B—C14—C13	125.3 (11)	N2—C25—C21	178.8 (8)
C15B—C14—H14C	106.0
O1—C2—C3—C4	0.3 (8)	C7—C8—C9—C10	−2.9 (7)
O1—C2—C3—C13	−178.1 (5)	C8—C9—C10—C4	−177.3 (5)
O1—C9—C10—C4	0.7 (7)	C8—C9—C10—C5	3.3 (7)
O1—C9—C10—C5	−178.6 (4)	C9—O1—C2—O2	178.7 (4)
O2—C2—C3—C4	179.1 (6)	C9—O1—C2—C3	−2.3 (8)
O2—C2—C3—C13	0.7 (9)	C10—C5—C6—C7	−1.7 (7)
O3—C7—C8—C9	−176.4 (4)	C11—C4—C10—C5	−4.5 (7)
O3—C7—C8—C12	3.2 (7)	C11—C4—C10—C9	176.2 (5)
O3—C18—C19—C20	179.6 (5)	C12—C8—C9—O1	−0.6 (7)
O3—C18—C23—C22	−178.9 (5)	C12—C8—C9—C10	177.5 (5)
C2—O1—C9—C8	180.0 (5)	C13—C3—C4—C10	−179.5 (5)
C2—O1—C9—C10	1.8 (7)	C13—C3—C4—C11	1.7 (8)
C2—C3—C4—C10	2.1 (8)	C13—C14—C15A—C16A	173.0 (14)
C2—C3—C4—C11	−176.7 (5)	C13—C14—C15B—C16B	70 (2)
C2—C3—C13—C14	−93.4 (8)	C14—C15A—C16A—C17A	174.6 (15)
C3—C4—C10—C5	176.7 (4)	C14—C15B—C16B—C17B	157 (2)
C3—C4—C10—C9	−2.6 (7)	C18—O3—C7—C6	56.2 (6)
C3—C13—C14—C15A	−170.4 (10)	C18—O3—C7—C8	−127.1 (5)
C3—C13—C14—C15B	172.1 (12)	C18—C19—C20—C21	−2.5 (7)
C4—C3—C13—C14	88.1 (7)	C18—C19—C20—C24	177.4 (5)
C5—C6—C7—O3	178.6 (4)	C19—C18—C23—C22	−0.5 (8)
C5—C6—C7—C8	2.1 (7)	C19—C20—C21—C22	2.8 (7)
C6—C5—C10—C4	179.7 (4)	C19—C20—C21—C25	−178.2 (5)
C6—C5—C10—C9	−0.9 (7)	C20—C21—C22—C23	−2.0 (8)
C6—C7—C8—C9	0.1 (7)	C21—C22—C23—C18	0.8 (8)
C6—C7—C8—C12	179.7 (5)	C23—C18—C19—C20	1.3 (7)
C7—O3—C18—C19	8.5 (7)	C24—C20—C21—C22	−177.1 (5)
C7—O3—C18—C23	−173.1 (4)	C24—C20—C21—C25	1.9 (7)
C7—C8—C9—O1	179.0 (4)	C25—C21—C22—C23	179.0 (5)

(21gtu181_fs_1_0m)

Crystal data

C16H20O3	Dx = 1.220 Mg m^−3
Mr = 260.32	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 1711 reflections
a = 29.189 (8) Å	θ = 2.7–22.6°
b = 5.5877 (15) Å	µ = 0.08 mm^−1
c = 8.686 (3) Å	T = 298 K
V = 1416.7 (7) Å^3	Block, colourless
Z = 4	0.19 × 0.14 × 0.10 mm
F(000) = 560

Data collection

Bruker APEX-II CCD diffractometer	2415 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	1700 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.057
Detector resolution: 7.9 pixels mm^-1	θmax = 25.0°, θmin = 1.4°
ω and φ scans	h = −34→32
Absorption correction: multi-scan SADABS V2014/4 (Bruker AXS)	k = −6→6
Tmin = 0.393, Tmax = 0.746	l = −10→10
6701 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.074	w = 1/[σ^2(Fo^2) + (0.1144P)^2 + 0.4608P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.211	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.28 e Å^−3
2415 reflections	Δρmin = −0.25 e Å^−3
186 parameters	Absolute structure: Flack x determined using 578 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
42 restraints	Absolute structure parameter: −0.6 (10)
Primary atom site location: dual

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	Occ. (<1)
O1	0.69987 (15)	0.1949 (7)	0.3862 (4)	0.0461 (11)
O2	0.64576 (17)	−0.0130 (8)	0.5000 (6)	0.0689 (15)
O3	0.82287 (16)	0.6022 (8)	0.1601 (6)	0.0637 (14)
H3	0.828015	0.713463	0.100982	0.096*
C2	0.6542 (2)	0.1560 (11)	0.4157 (7)	0.0526 (17)
C3	0.6204 (2)	0.3094 (11)	0.3446 (8)	0.0517 (16)
C4	0.6350 (2)	0.4920 (11)	0.2514 (7)	0.0509 (17)
C5	0.7006 (2)	0.7136 (11)	0.1311 (8)	0.0535 (18)
H5	0.680786	0.821728	0.084429	0.064*
C6	0.7464 (2)	0.7370 (10)	0.1080 (8)	0.0547 (17)
H6	0.757442	0.857500	0.044050	0.066*
C7	0.7773 (2)	0.5797 (10)	0.1803 (7)	0.0466 (15)
C8	0.7614 (2)	0.3959 (10)	0.2731 (7)	0.0434 (15)
C9	0.7145 (2)	0.3781 (10)	0.2927 (6)	0.0419 (14)
C10	0.6823 (2)	0.5299 (10)	0.2239 (7)	0.0415 (14)
C11	0.6006 (2)	0.6525 (14)	0.1714 (10)	0.071 (2)
H11A	0.602979	0.811838	0.211916	0.106*
H11B	0.570248	0.592357	0.188664	0.106*
H11C	0.606852	0.654917	0.062873	0.106*
C12	0.7942 (3)	0.2276 (12)	0.3499 (9)	0.0577 (18)
H12A	0.814341	0.159973	0.274177	0.087*
H12B	0.777367	0.101865	0.399630	0.087*
H12C	0.811856	0.313255	0.425110	0.087*
C13	0.5713 (3)	0.2591 (13)	0.3834 (10)	0.080 (2)
H13A	0.569141	0.094654	0.418424	0.096*
H13B	0.553452	0.271940	0.289659	0.096*
C14	0.5497 (4)	0.4167 (18)	0.5030 (10)	0.105 (3)
H14A	0.557089	0.581837	0.479100	0.126*	0.796 (18)
H14B	0.516684	0.399795	0.495827	0.126*	0.796 (18)
H14C	0.529292	0.518615	0.444043	0.126*	0.204 (18)
H14D	0.574552	0.520057	0.535751	0.126*	0.204 (18)
C15A	0.5637 (5)	0.3677 (18)	0.6644 (13)	0.102 (4)	0.796 (18)
H15A	0.554750	0.500998	0.729372	0.122*	0.796 (18)
H15B	0.596759	0.352241	0.669513	0.122*	0.796 (18)
C15B	0.5231 (10)	0.369 (4)	0.652 (3)	0.076 (8)	0.204 (18)
H15C	0.490677	0.353580	0.629011	0.091*	0.204 (18)
H15D	0.527185	0.500833	0.722570	0.091*	0.204 (18)
C16	0.5411 (4)	0.1346 (18)	0.7248 (12)	0.115 (3)
H16A	0.507961	0.150076	0.725187	0.138*	0.796 (18)
H16B	0.549360	−0.000251	0.660236	0.138*	0.796 (18)
H16C	0.516425	0.019513	0.712949	0.138*	0.204 (18)
H16D	0.565533	0.080555	0.657752	0.138*	0.204 (18)
C17	0.5590 (5)	0.098 (3)	0.8888 (13)	0.147 (5)
H17A	0.578034	0.231540	0.917003	0.221*
H17B	0.576643	−0.046502	0.893344	0.221*
H17C	0.533657	0.087464	0.958765	0.221*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.063 (3)	0.037 (2)	0.039 (2)	0.0047 (18)	0.006 (2)	0.009 (2)
O2	0.081 (3)	0.047 (3)	0.079 (3)	0.006 (2)	0.014 (3)	0.031 (3)
O3	0.069 (3)	0.046 (3)	0.076 (4)	−0.001 (2)	0.006 (3)	0.016 (3)
C2	0.077 (5)	0.035 (3)	0.047 (4)	0.004 (3)	0.014 (3)	0.001 (3)
C3	0.065 (4)	0.040 (3)	0.050 (4)	0.009 (3)	0.004 (3)	0.004 (3)
C4	0.063 (5)	0.042 (3)	0.048 (4)	0.012 (3)	0.005 (3)	0.005 (3)
C5	0.077 (5)	0.035 (3)	0.049 (4)	0.004 (3)	−0.002 (4)	0.020 (3)
C6	0.080 (5)	0.037 (3)	0.047 (4)	−0.001 (4)	0.003 (4)	0.018 (3)
C7	0.060 (4)	0.036 (3)	0.044 (4)	−0.001 (3)	−0.003 (3)	0.005 (3)
C8	0.069 (4)	0.027 (3)	0.035 (3)	0.003 (3)	0.000 (3)	0.003 (3)
C9	0.069 (4)	0.030 (3)	0.026 (3)	0.004 (3)	0.005 (3)	0.005 (3)
C10	0.058 (4)	0.036 (3)	0.030 (3)	0.009 (3)	0.000 (3)	0.006 (3)
C11	0.077 (5)	0.057 (4)	0.079 (5)	0.016 (4)	−0.002 (4)	0.025 (4)
C12	0.072 (5)	0.046 (4)	0.054 (4)	0.002 (3)	0.000 (3)	0.016 (3)
C13	0.082 (5)	0.059 (4)	0.099 (5)	0.015 (4)	0.024 (4)	0.024 (4)
C14	0.127 (8)	0.081 (5)	0.107 (5)	0.017 (5)	0.042 (5)	0.015 (4)
C15A	0.132 (11)	0.063 (5)	0.110 (5)	−0.002 (6)	0.011 (6)	−0.013 (5)
C15B	0.072 (17)	0.064 (12)	0.090 (10)	−0.026 (11)	0.010 (9)	−0.001 (9)
C16	0.146 (8)	0.091 (6)	0.109 (7)	−0.001 (5)	0.011 (6)	0.024 (5)
C17	0.136 (10)	0.180 (12)	0.125 (8)	0.008 (9)	−0.003 (7)	0.047 (8)

Geometric parameters (Å, º)

O1—C2	1.375 (8)	C12—H12C	0.9600
O1—C9	1.375 (7)	C13—H13A	0.9700
O2—C2	1.220 (7)	C13—H13B	0.9700
O3—H3	0.8200	C13—C14	1.501 (9)
O3—C7	1.347 (8)	C14—H14A	0.9700
C2—C3	1.446 (9)	C14—H14B	0.9700
C3—C4	1.371 (9)	C14—H14C	0.9700
C3—C13	1.497 (11)	C14—H14D	0.9700
C4—C10	1.416 (9)	C14—C15A	1.486 (10)
C4—C11	1.515 (9)	C14—C15B	1.529 (12)
C5—H5	0.9300	C15A—H15A	0.9700
C5—C6	1.359 (8)	C15A—H15B	0.9700
C5—C10	1.410 (9)	C15A—C16	1.552 (10)
C6—H6	0.9300	C15B—H15C	0.9700
C6—C7	1.407 (8)	C15B—H15D	0.9700
C7—C8	1.386 (8)	C15B—C16	1.546 (13)
C8—C9	1.384 (8)	C16—H16A	0.9700
C8—C12	1.498 (9)	C16—H16B	0.9700
C9—C10	1.400 (8)	C16—H16C	0.9700
C11—H11A	0.9600	C16—H16D	0.9700
C11—H11B	0.9600	C16—C17	1.531 (11)
C11—H11C	0.9600	C17—H17A	0.9600
C12—H12A	0.9600	C17—H17B	0.9600
C12—H12B	0.9600	C17—H17C	0.9600
C9—O1—C2	121.9 (5)	C14—C13—H13A	108.1
C7—O3—H3	109.5	C14—C13—H13B	108.1
O1—C2—C3	119.3 (5)	C13—C14—H14A	108.4
O2—C2—O1	115.4 (6)	C13—C14—H14B	108.4
O2—C2—C3	125.3 (6)	C13—C14—H14C	103.7
C2—C3—C13	116.4 (6)	C13—C14—H14D	103.7
C4—C3—C2	118.7 (6)	C13—C14—C15B	134.0 (12)
C4—C3—C13	124.8 (6)	H14A—C14—H14B	107.5
C3—C4—C10	121.0 (5)	H14C—C14—H14D	105.4
C3—C4—C11	120.3 (6)	C15A—C14—C13	115.4 (9)
C10—C4—C11	118.7 (5)	C15A—C14—H14A	108.4
C6—C5—H5	119.1	C15A—C14—H14B	108.4
C6—C5—C10	121.9 (6)	C15B—C14—H14C	103.7
C10—C5—H5	119.1	C15B—C14—H14D	103.7
C5—C6—H6	119.8	C14—C15A—H15A	109.5
C5—C6—C7	120.3 (6)	C14—C15A—H15B	109.5
C7—C6—H6	119.8	C14—C15A—C16	110.9 (9)
O3—C7—C6	121.1 (5)	H15A—C15A—H15B	108.1
O3—C7—C8	118.4 (5)	C16—C15A—H15A	109.5
C8—C7—C6	120.5 (6)	C16—C15A—H15B	109.5
C7—C8—C12	120.7 (6)	C14—C15B—H15C	109.9
C9—C8—C7	117.1 (5)	C14—C15B—H15D	109.9
C9—C8—C12	122.2 (5)	C14—C15B—C16	108.9 (11)
O1—C9—C8	115.7 (5)	H15C—C15B—H15D	108.3
O1—C9—C10	119.7 (5)	C16—C15B—H15C	109.9
C8—C9—C10	124.6 (5)	C16—C15B—H15D	109.9
C5—C10—C4	125.1 (5)	C15A—C16—H16A	110.5
C9—C10—C4	119.4 (5)	C15A—C16—H16B	110.5
C9—C10—C5	115.5 (6)	C15B—C16—H16C	105.4
C4—C11—H11A	109.5	C15B—C16—H16D	105.4
C4—C11—H11B	109.5	H16A—C16—H16B	108.7
C4—C11—H11C	109.5	H16C—C16—H16D	106.0
H11A—C11—H11B	109.5	C17—C16—C15A	106.2 (10)
H11A—C11—H11C	109.5	C17—C16—C15B	127.7 (17)
H11B—C11—H11C	109.5	C17—C16—H16A	110.5
C8—C12—H12A	109.5	C17—C16—H16B	110.5
C8—C12—H12B	109.5	C17—C16—H16C	105.4
C8—C12—H12C	109.5	C17—C16—H16D	105.4
H12A—C12—H12B	109.5	C16—C17—H17A	109.5
H12A—C12—H12C	109.5	C16—C17—H17B	109.5
H12B—C12—H12C	109.5	C16—C17—H17C	109.5
C3—C13—H13A	108.1	H17A—C17—H17B	109.5
C3—C13—H13B	108.1	H17A—C17—H17C	109.5
C3—C13—C14	116.6 (8)	H17B—C17—H17C	109.5
H13A—C13—H13B	107.3
O1—C2—C3—C4	−1.0 (9)	C6—C5—C10—C9	1.4 (10)
O1—C2—C3—C13	−179.2 (6)	C6—C7—C8—C9	−1.1 (9)
O1—C9—C10—C4	−0.2 (8)	C6—C7—C8—C12	179.8 (6)
O1—C9—C10—C5	179.5 (6)	C7—C8—C9—O1	−179.6 (5)
O2—C2—C3—C4	−179.5 (6)	C7—C8—C9—C10	0.9 (9)
O2—C2—C3—C13	2.2 (10)	C8—C9—C10—C4	179.3 (6)
O3—C7—C8—C9	179.5 (5)	C8—C9—C10—C5	−1.1 (9)
O3—C7—C8—C12	0.4 (9)	C9—O1—C2—O2	179.7 (5)
C2—O1—C9—C8	−179.9 (5)	C9—O1—C2—C3	1.0 (8)
C2—O1—C9—C10	−0.4 (8)	C10—C5—C6—C7	−1.6 (11)
C2—C3—C4—C10	0.4 (9)	C11—C4—C10—C5	2.5 (9)
C2—C3—C4—C11	178.3 (6)	C11—C4—C10—C9	−177.8 (6)
C2—C3—C13—C14	100.1 (8)	C12—C8—C9—O1	−0.5 (8)
C3—C4—C10—C5	−179.4 (7)	C12—C8—C9—C10	−180.0 (6)
C3—C4—C10—C9	0.2 (9)	C13—C3—C4—C10	178.4 (6)
C3—C13—C14—C15A	−75.1 (10)	C13—C3—C4—C11	−3.6 (11)
C3—C13—C14—C15B	−128 (2)	C13—C14—C15A—C16	−74.0 (13)
C4—C3—C13—C14	−78.0 (10)	C13—C14—C15B—C16	32 (4)
C5—C6—C7—O3	−179.2 (6)	C14—C15A—C16—C17	178.2 (11)
C5—C6—C7—C8	1.5 (10)	C14—C15B—C16—C17	125.6 (19)
C6—C5—C10—C4	−179.0 (6)