organic papers
Acta Cryst.(2006). E62, o1819–o1821 doi:10.1107/S1600536806011792 Saeed and Flo¨rke C
17H17ClO3
o1819
Acta Crystallographica Section E Structure Reports Online
ISSN 1600-5368
1-(4-Chlorophenyl)-6,7-dimethoxyisochroman
Aamer Saeedaand Ulrich Flo¨rkeb*
a
Department of Chemistry, Quaid-i-Azam University Islamabad, Pakistan, and b
Department Chemie, Fakulta¨t fu¨r Naturwissenschaften, Universita¨t Paderborn, Warburgerstr. 100, D-33098 Paderborn, Germany
Correspondence e-mail: ulrich.floerke@upb.de
Key indicators
Single-crystal X-ray study
T= 120 K
Mean(C–C) = 0.002 A˚
Rfactor = 0.042
wRfactor = 0.115
Data-to-parameter ratio = 18.6
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 28 March 2006 Accepted 31 March 2006
#2006 International Union of Crystallography
All rights reserved
The title compound, C17H17ClO3, is another representative of
the rare examples of crystallographically characterized 6,7-dimethoxyisochromans. The packing exhibits intermolecular
C(methyl)—H Cl hydrogen bonds with an infinite zigzag
pattern along [010]. Additional intermolecular bonds occur between methoxy groups and the pyran O atoms.
Comment
Various isochroman (3,4-dihydro-1H-benzo[c]pyran)
struc-tures are found in nature or as part of complex natural products. These are also intermediates in the synthesis of pharmaceuticals and drugs. 1-Aryl-6,7-dimethoxyisochromans are an important class of isochromans which exhibit a wide range of biological activities such as analgesic, muscle relaxant, antidepressant, anti-inflammatory, antihistaminic,
anticoagulant and antihypertensive (Dobson et al., 1975;
Yamato et al., 1985; McCall et al., 1982).
6,7-Dimethoxy-isochromans substituted at C-1 via a one- to three-carbon
chain with arylpiperazines,p-fluorophenyl,etc., are hypoten-sives which lower blood pressure, presumably by both
peripheral and central-adrenoreceptor blockade (TenBrink
et al., 1996). 1-Phenyl- and 1-(3-methoxy-4-hydroxy)phenyl-6,7-dihydroxyisochromans have been identified in extra virgin olive oil (Malstromet al., 2000). These natural isochromans or their synthetic derivatives have been shown to exhibit bene-ficial antioxidant effects (Lorenzet al., 2005). The antiplatelet activity and antioxidant power of these isochromans have also been evaluated and found to be effective free radical scavengers and inhibited platelet aggregation and throm-boxane release evoked by agonists (Tognaet al., 2003).
6,7-Dimethoxyisochromans can easily be demethylated to the corresponding 6,7-dihydroxyisochromans. The oxa-Pictet– Spengler reaction is a variation of the Pictet–Spengler reaction in which a phenethyl alcohol reacts with a carbonyl compound
2001). The title compound, (I), was prepared by condensation
of 2-(3,4-dimethoxyphenyl)ethanol with
4-chlorobenz-aldehyde in the presence of a catalytic amount of p
-toluene-sulfonic acid under microwave irradiation. The compound was
characterized by a 1H singlet at5.54 for H-1 in the1H NMR
spectrum. The non-planar nature of the tetrahydropyran ring
was indicated by separate 2H multiplets at3.84 and 4.0 and
at 2.56 and 2.94 for the C-3 and C-4 methylene protons,
respectively.
The pyran ring is puckered with O1 and C8 lying0.429 (1)
and 0.342 (2)A˚ , respectively, below and above the isochroman plane. The C atom of the O3/C17 methoxy group is slightly
bent out of this plane [C17 0.325 (2), with A˚ below the plane], whereas the second methoxy group is almost coplanar [deviation for C16 of 0.066 (2)A˚ ]. The angle formed by the two aromatic isochroman (C10–C15) and benzene (C1–C6) planes is 84.30 (4).
The packing shows stacking of the molecules along [010].
Intermolecular C—H Cl hydrogen bonds (see Table) form a
zigzag pattern with each of the two methyl donors linked to one chlorine acceptor. These infinite centrosymmetric double chains (Fig. 2) are then connected to each other by
C(methyl)—H O(pyran) bridges. The shortest
inter-molecular H O(methoxy) distances are about 2.7A˚ and
there are no–interactions between the molecules. There
are short C—H contacts between C3—H3 and X1(x+ 1,
y+1 2,z+
1
2), the mid-point of the C1–C6p-chlorophenyl ring,
and between C16—H16Aand X2(x,y+ 1,z), the mid-point of the C10–C15 dimethoxyisochroman unit.
Experimental
To a mixture of 2-(3,4-dimethoxyphenyl)ethanol (0.182 g, 1 mmol) and 4-chlorobenzaldehyde (0.136 g, 0.12 ml, 1 mmol), a catalytic amount of p-toluenesulfonic acid monohydrate was added. The reaction mixture was homogenized and irradiated for 90 s. On completion of the reaction, as monitored by thin-layer chromato-graphy (TLC, every 30 s) using petroleum ether and ethyl acetate (7:2), the reaction mixture was purified by thick-layer chromato-graphy. The product obtained was recrystallized from ethyl acetate (0.29 g, 0.98 mmol, 98%; 357–358 K). TLC (Rf): 0.38; 1H NMR (CDCl3):6.59 (1H,s, H-5), 6.20 (1H,s, H-8), 5.54 (1H,s, H-1), 3.84 and 4.0 (2H,m, 2H-3), 3.79 (6H,s, 2OCH3), 2.56 and 2.94 (2H, m, 2H-4); chlorophenyl group: 7.23 (2H,d,J= 8.4 Hz, C-30and
C-50), 7.20 (2H,d,J= 8.4 Hz, C-20 and C-60). Analysis calculated for
C17H17ClO3: C 67.00, H 5.62%; found: C 67.3, H 5.58%.
Crystal data
C17H17ClO3
Mr= 304.76 Monoclinic,P21=c
a= 16.877 (1) A˚
b= 5.3142 (3) A˚
c= 16.3985 (9) A˚
= 96.964 (1)
V= 1459.89 (14) A˚3
Z= 4
Dx= 1.387 Mg m 3
MoKradiation
= 0.27 mm1
T= 120 (2) K Block, colourless 0.420.260.25 mm
Data collection
Bruker SMART CCD area-detector diffractometer
’and!scans
Absorption correction: multi-scan (SADABS; Bruker, 2002)
Tmin= 0.895,Tmax= 0.936
13531 measured reflections 3531 independent reflections 3050 reflections withI> 2(I)
Rint= 0.025
max= 28.1
Refinement
Refinement onF2
R[F2> 2(F2)] = 0.042
wR(F2) = 0.115
S= 1.04 3531 reflections 190 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.0609P)2 + 0.562P]
whereP= (Fo2+ 2Fc2)/3 (/)max< 0.001
max= 0.39 e A˚ 3
min=0.37 e A˚ 3
organic papers
o1820
Saeed and Flo¨rke C [image:2.610.61.262.68.313.2]17H17ClO3 Acta Cryst.(2006). E62, o1819–o1821
Figure 1
[image:2.610.46.294.358.539.2]The molecular structure of (I). Displacement ellipsoids are drawn at the 50% probability level.
Figure 2
Table 1
Selected geometric parameters (A˚ ,).
Cl1—C4 1.7427 (15)
O1—C8 1.4294 (17)
O1—C7 1.4302 (18)
C1—C7 1.5102 (19)
C8—O1—C7 110.94 (11)
O1—C7—C1 106.73 (11)
O1—C7—C11 110.98 (12)
C1—C7—C11 113.34 (11)
C2—C1—C7—C11 117.11 (15)
C16—O2—C13—C14 177.65 (12)
C17—O3—C14—C13 167.44 (12)
Table 2
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
C16—H16B O1i
0.98 2.59 3.5375 (19) 164
C16—H16B Cl1ii
0.98 2.88 3.3115 (14) 108
C16—H16C Cl1iii
0.98 2.89 3.7440 (17) 146
Symmetry codes: (i) x;yþ3 2;zþ
1
2; (ii) xþ1;yþ2;zþ1; (iii)
xþ1;yþ1;zþ1.
H atoms were placed at idealized positions (C–H = 0.95–0.99A˚ ) and refined as riding, withUiso(H) = 1.2Ueq(C) and 1.5Ueq(methyl C). Data collection:SMART(Bruker, 2002); cell refinement:SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve
structure: SHELXTL (Bruker, 2002); program(s) used to refine structure:SHELXTL; molecular graphics:SHELXTL; software used to prepare material for publication:SHELXTL.
AS gratefully acknowledges the Higher Education
Commission of Pakistan for financial assistance.
References
Bruker (2002).SMART(Version 5.62),SAINT (Version 6.02),SHELXTL
(Version 6.10) andSADABS(Version 2.03). Bruker AXS Inc., Madison, Wisconsin, USA.
Dobson, T. A. & Humber, L. G. (1975).J. Heterocycl. Chem.12, 591–594. Guiso, M., Marra, C. & Cavarischia, C. (2001).Tetrahedron Lett.42, 6531–
6134.
Lorenz, P., Zeh, M., Lobenhoffer, J. M., Schmidt, H., Wolf, G. & Horn, T. F. W. (2005).Free Radical Res.39, 535–545.
Malstrom, J., Christophersen, C. & Frisvad, J. C. (2000).Phytochemistry,54, 301–309.
McCall, J. M., McCall, R. B., TenBrink, R. E., Kamdar, B. V., Humphrey, S. J., Sethy, V. H., Harris, D. W. & Daenzar, C. (1982).J. Med. Chem.25, 75–81. TenBrink, R. E., Bergh, C. L., Duncan, J. N., Harris, D. W., Huff, R. M., Lahti, R. A., Lawson, C. F., Lutzke, B. S., Martin, I. J., Rees, S. A., Schlachter, S. K., Sihr, J. C. & Smith, M. W. (1996).J. Med. Chem.39, 2435–2437.
Togna, G. I., Togna, A. R., Franconi, M., Marra, C. & Guiso, M. (2003).J. Nutr. 133, 2532–2536.
Yamato, M., Hashigaki, K., Ishikawa, S., Kokubu, N., Inoue, Y., Tsuruo, T. & Tashirot, T. (1985).J. Med. Chem.28, 1026–1031.
organic papers
Acta Cryst.(2006). E62, o1819–o1821 Saeed and Flo¨rke C
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Acta Cryst. (2006). E62, o1819–o1821
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Acta Cryst. (2006). E62, o1819–o1821 [https://doi.org/10.1107/S1600536806011792]
1-(4-Chlorophenyl)-6,7-dimethoxyisochroman
Aamer Saeed and Ulrich Fl
ö
rke
1-(4-Chlorophenyl)-6,7-dimethoxyisochroman
Crystal data
C17H17ClO3
Mr = 304.76
Monoclinic, P21/c
Hall symbol: -P 2ybc
a = 16.877 (1) Å
b = 5.3142 (3) Å
c = 16.3985 (9) Å
β = 96.964 (1)°
V = 1459.89 (14) Å3
Z = 4
F(000) = 640
Dx = 1.387 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 4340 reflections
θ = 2.4–28.2°
µ = 0.27 mm−1
T = 120 K Block, colourless 0.42 × 0.26 × 0.25 mm
Data collection
Bruker SMART CCD area-detector diffractometer
Radiation source: sealed tube Graphite monochromator
φ and ω scans
Absorption correction: multi-scan (SADABS; Bruker, 2002)
Tmin = 0.895, Tmax = 0.936
13531 measured reflections 3531 independent reflections 3050 reflections with I > 2σ(I)
Rint = 0.025
θmax = 28.1°, θmin = 1.2°
h = −22→22
k = −6→7
l = −19→21
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.042
wR(F2) = 0.115
S = 1.04 3531 reflections 190 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: difference Fourier map H-atom parameters constrained
w = 1/[σ2(F
o2) + (0.0609P)2 + 0.562P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.39 e Å−3
Δρmin = −0.37 e Å−3
Special details
Experimental. EIMS m/e: 304, 306, 193, 165.
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Acta Cryst. (2006). E62, o1819–o1821
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2,
conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used
only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2
are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
Cl1 0.38719 (2) 0.54092 (9) 0.38286 (3) 0.04020 (14) O1 0.74629 (6) 0.2315 (2) 0.30335 (6) 0.0292 (2) O2 0.81316 (6) 0.8414 (2) 0.61986 (6) 0.0275 (2) O3 0.93535 (6) 0.5440 (2) 0.64814 (6) 0.0257 (2) C1 0.64861 (8) 0.4869 (3) 0.35364 (8) 0.0224 (3) C2 0.60322 (9) 0.6852 (3) 0.31898 (10) 0.0299 (3)
H2A 0.6274 0.8102 0.2888 0.036*
C3 0.52254 (9) 0.7033 (3) 0.32791 (10) 0.0326 (3)
H3A 0.4915 0.8395 0.3040 0.039*
C4 0.48841 (8) 0.5214 (3) 0.37180 (9) 0.0268 (3) C5 0.53228 (9) 0.3215 (3) 0.40710 (9) 0.0289 (3)
H5A 0.5078 0.1968 0.4372 0.035*
C6 0.61262 (8) 0.3064 (3) 0.39775 (9) 0.0270 (3)
H6A 0.6435 0.1703 0.4220 0.032*
C7 0.73616 (8) 0.4658 (3) 0.34375 (9) 0.0246 (3)
H7A 0.7504 0.6054 0.3073 0.029*
C8 0.82828 (9) 0.1903 (3) 0.29347 (9) 0.0314 (3)
H8A 0.8500 0.3408 0.2683 0.038*
H8B 0.8327 0.0457 0.2562 0.038*
C9 0.87619 (9) 0.1379 (3) 0.37581 (9) 0.0275 (3)
H9A 0.8640 −0.0337 0.3942 0.033*
H9B 0.9339 0.1458 0.3701 0.033*
C10 0.85689 (8) 0.3271 (3) 0.43923 (8) 0.0226 (3) C11 0.79063 (8) 0.4813 (3) 0.42494 (8) 0.0213 (3) C12 0.77495 (8) 0.6579 (3) 0.48436 (8) 0.0221 (3)
H12A 0.7299 0.7655 0.4739 0.027*
C13 0.82405 (8) 0.6780 (3) 0.55810 (8) 0.0216 (3) C14 0.89049 (8) 0.5168 (3) 0.57309 (9) 0.0213 (3) C15 0.90621 (8) 0.3459 (3) 0.51397 (9) 0.0231 (3)
H15A 0.9514 0.2388 0.5241 0.028*
C16 0.74778 (9) 1.0131 (3) 0.60433 (9) 0.0274 (3)
H16A 0.7564 1.1226 0.5581 0.041*
H16B 0.7441 1.1158 0.6534 0.041*
H16C 0.6981 0.9184 0.5909 0.041*
C17 0.99185 (9) 0.3487 (3) 0.67008 (9) 0.0286 (3)
H17A 0.9653 0.1849 0.6627 0.043*
H17B 1.0143 0.3686 0.7277 0.043*
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Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
Cl1 0.0257 (2) 0.0487 (3) 0.0464 (3) 0.00991 (16) 0.00516 (16) −0.00744 (19) O1 0.0264 (5) 0.0341 (6) 0.0282 (5) −0.0030 (4) 0.0080 (4) −0.0111 (5) O2 0.0304 (5) 0.0274 (5) 0.0240 (5) 0.0095 (4) 0.0000 (4) −0.0053 (4) O3 0.0244 (5) 0.0279 (5) 0.0240 (5) 0.0053 (4) 0.0003 (4) −0.0010 (4) C1 0.0251 (6) 0.0230 (7) 0.0186 (6) −0.0003 (5) 0.0009 (5) −0.0033 (5) C2 0.0369 (8) 0.0239 (7) 0.0289 (7) −0.0004 (6) 0.0041 (6) 0.0034 (6) C3 0.0354 (8) 0.0269 (8) 0.0344 (8) 0.0096 (6) −0.0001 (6) 0.0023 (6) C4 0.0234 (6) 0.0299 (8) 0.0269 (7) 0.0046 (5) 0.0013 (5) −0.0073 (6) C5 0.0278 (7) 0.0292 (8) 0.0302 (8) 0.0009 (6) 0.0064 (6) 0.0034 (6) C6 0.0253 (7) 0.0257 (7) 0.0298 (7) 0.0033 (5) 0.0025 (5) 0.0057 (6) C7 0.0268 (7) 0.0260 (7) 0.0214 (7) −0.0032 (5) 0.0050 (5) −0.0012 (5) C8 0.0291 (7) 0.0389 (9) 0.0283 (8) −0.0031 (6) 0.0124 (6) −0.0094 (7) C9 0.0278 (7) 0.0260 (7) 0.0309 (8) −0.0006 (6) 0.0125 (6) −0.0050 (6) C10 0.0243 (6) 0.0218 (7) 0.0235 (7) −0.0022 (5) 0.0096 (5) −0.0009 (5) C11 0.0223 (6) 0.0213 (7) 0.0211 (6) −0.0034 (5) 0.0056 (5) 0.0009 (5) C12 0.0220 (6) 0.0208 (7) 0.0239 (7) 0.0020 (5) 0.0045 (5) 0.0004 (5) C13 0.0241 (6) 0.0189 (6) 0.0228 (7) 0.0010 (5) 0.0066 (5) −0.0009 (5) C14 0.0198 (6) 0.0218 (7) 0.0227 (7) −0.0011 (5) 0.0044 (5) 0.0024 (5) C15 0.0199 (6) 0.0232 (7) 0.0275 (7) 0.0018 (5) 0.0076 (5) 0.0015 (5) C16 0.0278 (7) 0.0255 (7) 0.0286 (8) 0.0073 (6) 0.0028 (6) −0.0046 (6) C17 0.0268 (7) 0.0296 (8) 0.0285 (7) 0.0057 (6) 0.0002 (6) 0.0040 (6)
Geometric parameters (Å, º)
Cl1—C4 1.7427 (15) C8—C9 1.513 (2)
O1—C8 1.4294 (17) C8—H8A 0.9900
O1—C7 1.4302 (18) C8—H8B 0.9900
O2—C13 1.3633 (16) C9—C10 1.5100 (19)
O2—C16 1.4306 (16) C9—H9A 0.9900
O3—C14 1.3720 (17) C9—H9B 0.9900
O3—C17 1.4259 (17) C10—C11 1.3832 (19)
C1—C2 1.384 (2) C10—C15 1.399 (2)
C1—C6 1.385 (2) C11—C12 1.4012 (19)
C1—C7 1.5102 (19) C12—C13 1.3848 (19)
C2—C3 1.390 (2) C12—H12A 0.9500
C2—H2A 0.9500 C13—C14 1.4091 (18)
C3—C4 1.373 (2) C14—C15 1.377 (2)
C3—H3A 0.9500 C15—H15A 0.9500
C4—C5 1.381 (2) C16—H16A 0.9800
C5—C6 1.385 (2) C16—H16B 0.9800
C5—H5A 0.9500 C16—H16C 0.9800
C6—H6A 0.9500 C17—H17A 0.9800
C7—C11 1.5255 (19) C17—H17B 0.9800
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Acta Cryst. (2006). E62, o1819–o1821
C8—O1—C7 110.94 (11) C8—C9—H9A 109.5
C13—O2—C16 116.39 (11) C10—C9—H9B 109.5
C14—O3—C17 115.40 (11) C8—C9—H9B 109.5
C2—C1—C6 119.07 (13) H9A—C9—H9B 108.1
C2—C1—C7 120.84 (13) C11—C10—C15 119.28 (13)
C6—C1—C7 120.10 (12) C11—C10—C9 121.00 (13)
C1—C2—C3 120.66 (14) C15—C10—C9 119.72 (13)
C1—C2—H2A 119.7 C10—C11—C12 119.73 (13)
C3—C2—H2A 119.7 C10—C11—C7 120.34 (12)
C4—C3—C2 119.01 (14) C12—C11—C7 119.90 (12)
C4—C3—H3A 120.5 C13—C12—C11 121.04 (12)
C2—C3—H3A 120.5 C13—C12—H12A 119.5
C3—C4—C5 121.57 (14) C11—C12—H12A 119.5
C3—C4—Cl1 119.44 (12) O2—C13—C12 125.29 (12)
C5—C4—Cl1 118.99 (12) O2—C13—C14 115.71 (12)
C4—C5—C6 118.71 (14) C12—C13—C14 118.99 (12)
C4—C5—H5A 120.6 O3—C14—C15 124.64 (12)
C6—C5—H5A 120.6 O3—C14—C13 115.67 (12)
C1—C6—C5 120.99 (14) C15—C14—C13 119.68 (13)
C1—C6—H6A 119.5 C14—C15—C10 121.25 (13)
C5—C6—H6A 119.5 C14—C15—H15A 119.4
O1—C7—C1 106.73 (11) C10—C15—H15A 119.4
O1—C7—C11 110.98 (12) O2—C16—H16A 109.5
C1—C7—C11 113.34 (11) O2—C16—H16B 109.5
O1—C7—H7A 108.6 H16A—C16—H16B 109.5
C1—C7—H7A 108.6 O2—C16—H16C 109.5
C11—C7—H7A 108.6 H16A—C16—H16C 109.5
O1—C8—C9 110.30 (11) H16B—C16—H16C 109.5
O1—C8—H8A 109.6 O3—C17—H17A 109.5
C9—C8—H8A 109.6 O3—C17—H17B 109.5
O1—C8—H8B 109.6 H17A—C17—H17B 109.5
C9—C8—H8B 109.6 O3—C17—H17C 109.5
H8A—C8—H8B 108.1 H17A—C17—H17C 109.5
C10—C9—C8 110.83 (12) H17B—C17—H17C 109.5
C10—C9—H9A 109.5
C6—C1—C2—C3 −0.2 (2) C15—C10—C11—C7 179.60 (12)
C7—C1—C2—C3 179.70 (14) C9—C10—C11—C7 −1.0 (2)
C1—C2—C3—C4 0.1 (2) O1—C7—C11—C10 19.95 (17)
C2—C3—C4—C5 0.0 (2) C1—C7—C11—C10 140.02 (13)
C2—C3—C4—Cl1 −179.58 (12) O1—C7—C11—C12 −162.06 (12)
C3—C4—C5—C6 0.2 (2) C1—C7—C11—C12 −41.99 (17)
Cl1—C4—C5—C6 179.69 (12) C10—C11—C12—C13 −1.1 (2)
C2—C1—C6—C5 0.3 (2) C7—C11—C12—C13 −179.15 (12)
C7—C1—C6—C5 −179.59 (14) C16—O2—C13—C12 −3.4 (2)
C4—C5—C6—C1 −0.3 (2) C16—O2—C13—C14 177.65 (12)
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sup-5
Acta Cryst. (2006). E62, o1819–o1821
C2—C1—C7—O1 −120.43 (14) C17—O3—C14—C15 −12.33 (19) C6—C1—C7—O1 59.50 (17) C17—O3—C14—C13 167.44 (12) C2—C1—C7—C11 117.11 (15) O2—C13—C14—O3 0.39 (18) C6—C1—C7—C11 −62.97 (17) C12—C13—C14—O3 −178.65 (12) C7—O1—C8—C9 70.22 (16) O2—C13—C14—C15 −179.83 (12) O1—C8—C9—C10 −47.17 (17) C12—C13—C14—C15 1.1 (2) C8—C9—C10—C11 14.14 (18) O3—C14—C15—C10 179.09 (13) C8—C9—C10—C15 −166.42 (12) C13—C14—C15—C10 −0.7 (2) C15—C10—C11—C12 1.6 (2) C11—C10—C15—C14 −0.7 (2) C9—C10—C11—C12 −178.95 (12) C9—C10—C15—C14 179.84 (13)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
C16—H16B···O1i 0.98 2.59 3.5375 (19) 164
C16—H16B···Cl1ii 0.98 2.88 3.3115 (14) 108
C16—H16C···Cl1iii 0.98 2.89 3.7440 (17) 146