2,2-Di­chloro-6-methoxy-3,4-di­hydro-2H-naphthalene

The structure of the title compound, C₁₁H₁₀Cl₂O₂, shows that the asymmetric unit contains two closely related independent mol­ecules that pack in a head-to-tail arrangement.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.042
• wR factor = 0.125
• Data-to-parameter ratio = 18.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: MSC/AFC7 Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC7 Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1997–2001); program(s) used to solve structure: TEXSAN; program(s) used to refine structure: TEXSAN; SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN; PLATON (Spek, 2001).

2,2-dichloro-6-methoxy-3,4-dihydro-2H-naphthalene

Crystal data

C11H10Cl2O2	F(000) = 1008
Mr = 245.09	Dx = 1.498 Mg m^−3
Monoclinic, P21/c	Melting point = 358–360 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71069 Å
a = 17.569 (5) Å	Cell parameters from 25 reflections
b = 10.745 (3) Å	θ = 12.6–17.1°
c = 12.239 (4) Å	µ = 0.57 mm^−1
β = 109.83 (2)°	T = 295 K
V = 2173.5 (12) Å^3	Prismatic, colorless
Z = 8	0.30 × 0.30 × 0.14 mm

Data collection

Rigaku AFC7R diffractometer	Rint = 0.040
Radiation source: Rigaku rotating anode	θmax = 27.5°, θmin = 2.6°
Graphite monochromator	h = −10→22
ω–2θ scans	k = −13→6
6026 measured reflections	l = −15→14
4967 independent reflections	3 standard reflections every 150 reflections
2849 reflections with I > 2σ(I)	intensity decay: −4.8%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H-atom parameters not refined
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0484P)^2 + 0.7378P] where P = (Fo^2 + 2Fc^2)/3
4967 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

Experimental. The scan width was (1.73 + 0.30tanθ)° with an ω scan speed of 16° per minute (up to 4 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.68166 (6)	0.95196 (7)	0.51981 (8)	0.0640 (3)
Cl2	0.78694 (5)	0.77739 (7)	0.68095 (7)	0.0594 (3)
O1	0.60019 (14)	0.84924 (18)	0.67073 (19)	0.0619 (8)
O6	0.53343 (12)	0.27044 (17)	0.64489 (19)	0.0530 (7)
C1	0.62726 (16)	0.7666 (2)	0.6273 (2)	0.0396 (8)
C2	0.68993 (16)	0.7964 (2)	0.5681 (2)	0.0409 (8)
C3	0.68292 (17)	0.7093 (2)	0.4670 (2)	0.0441 (9)
C4	0.68842 (17)	0.5737 (2)	0.5037 (2)	0.0440 (9)
C5	0.61036 (16)	0.4195 (2)	0.5766 (2)	0.0403 (8)
C6	0.55988 (16)	0.3882 (2)	0.6374 (2)	0.0405 (8)
C7	0.53218 (17)	0.4792 (3)	0.6962 (2)	0.0431 (9)
C8	0.55439 (16)	0.6004 (2)	0.6916 (2)	0.0412 (8)
C9	0.60559 (15)	0.6349 (2)	0.6296 (2)	0.0362 (8)
C10	0.63345 (15)	0.5430 (2)	0.5714 (2)	0.0353 (8)
C61	0.5657 (2)	0.1709 (3)	0.5957 (3)	0.0612 (11)
Cl1'	0.81153 (6)	0.07311 (7)	0.83721 (7)	0.0615 (3)
Cl2'	0.70864 (5)	0.25595 (7)	0.89217 (8)	0.0603 (3)
O1'	0.89307 (14)	0.17288 (18)	1.06848 (18)	0.0623 (8)
O6'	0.96992 (13)	0.74875 (17)	1.11404 (18)	0.0574 (7)
C1'	0.86790 (17)	0.2568 (2)	0.9990 (2)	0.0423 (9)
C2'	0.80653 (17)	0.2301 (2)	0.8780 (2)	0.0418 (8)
C3'	0.81722 (17)	0.3154 (3)	0.7858 (2)	0.0453 (9)
C4'	0.81357 (18)	0.4512 (3)	0.8177 (2)	0.0492 (9)
C5'	0.89229 (16)	0.6025 (2)	0.9682 (2)	0.0423 (9)
C6'	0.94150 (16)	0.6326 (2)	1.0790 (2)	0.0426 (9)
C7'	0.96594 (17)	0.5406 (3)	1.1646 (2)	0.0453 (9)
C8'	0.94162 (17)	0.4202 (2)	1.1372 (2)	0.0441 (9)
C9'	0.89175 (16)	0.3875 (2)	1.0245 (2)	0.0383 (8)
C10'	0.86709 (16)	0.4805 (2)	0.9393 (2)	0.0381 (8)
C61'	0.9401 (2)	0.8489 (3)	1.0332 (3)	0.0662 (11)
H5	0.62950	0.35650	0.53800	0.0480*
H7	0.49810	0.45710	0.73910	0.0520*
H8	0.53500	0.66240	0.73090	0.0490*
H31	0.63230	0.72290	0.40750	0.0530*
H32	0.72550	0.72690	0.43790	0.0530*
H41	0.67390	0.52310	0.43610	0.0530*
H42	0.74260	0.55620	0.55080	0.0530*
H61	0.55200	0.18390	0.51450	0.0740*
H62	0.54360	0.09400	0.60900	0.0740*
H63	0.62290	0.16890	0.63110	0.0740*
H5'	0.87540	0.66580	0.91080	0.0510*
H7'	0.99930	0.56140	1.24140	0.0540*
H8'	0.95870	0.35770	1.19530	0.0530*
H31'	0.77550	0.29940	0.71410	0.0540*
H32'	0.86830	0.29930	0.77790	0.0540*
H41'	0.75930	0.47090	0.81030	0.0590*
H42'	0.83000	0.50090	0.76540	0.0590*
H61'	0.94800	0.82940	0.96210	0.0800*
H62'	0.88400	0.86050	1.01960	0.0800*
H63'	0.96860	0.92320	1.06440	0.0800*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0920 (6)	0.0361 (4)	0.0747 (5)	0.0056 (4)	0.0424 (5)	0.0143 (4)
Cl2	0.0501 (4)	0.0584 (5)	0.0615 (5)	−0.0076 (4)	0.0083 (4)	0.0027 (4)
O1	0.0863 (16)	0.0385 (11)	0.0788 (16)	0.0008 (10)	0.0515 (13)	−0.0083 (10)
O6	0.0571 (12)	0.0354 (10)	0.0754 (14)	−0.0037 (9)	0.0341 (11)	0.0023 (9)
C1	0.0476 (16)	0.0363 (13)	0.0376 (14)	0.0042 (12)	0.0179 (12)	0.0006 (11)
C2	0.0465 (16)	0.0330 (13)	0.0440 (15)	0.0017 (11)	0.0162 (12)	0.0040 (11)
C3	0.0512 (16)	0.0450 (15)	0.0443 (15)	−0.0011 (12)	0.0270 (13)	0.0023 (12)
C4	0.0482 (16)	0.0402 (14)	0.0519 (16)	−0.0019 (12)	0.0278 (14)	−0.0050 (12)
C5	0.0407 (15)	0.0342 (13)	0.0485 (16)	0.0019 (11)	0.0182 (12)	−0.0048 (11)
C6	0.0394 (15)	0.0373 (14)	0.0444 (15)	−0.0014 (11)	0.0137 (12)	0.0020 (11)
C7	0.0452 (16)	0.0465 (16)	0.0449 (15)	−0.0034 (12)	0.0248 (13)	−0.0006 (12)
C8	0.0477 (16)	0.0417 (14)	0.0384 (14)	−0.0005 (12)	0.0202 (12)	−0.0061 (11)
C9	0.0398 (14)	0.0345 (13)	0.0344 (13)	−0.0006 (10)	0.0128 (11)	−0.0033 (10)
C10	0.0359 (14)	0.0366 (13)	0.0349 (13)	0.0003 (11)	0.0141 (11)	−0.0013 (11)
C61	0.069 (2)	0.0342 (15)	0.084 (2)	−0.0032 (14)	0.0306 (19)	−0.0041 (15)
Cl1'	0.0875 (6)	0.0379 (4)	0.0627 (5)	0.0010 (4)	0.0303 (4)	−0.0077 (3)
Cl2'	0.0536 (5)	0.0570 (5)	0.0789 (6)	−0.0021 (4)	0.0335 (4)	0.0019 (4)
O1'	0.0944 (17)	0.0386 (11)	0.0490 (12)	0.0061 (11)	0.0180 (12)	0.0113 (9)
O6'	0.0650 (14)	0.0397 (11)	0.0576 (13)	−0.0063 (10)	0.0080 (11)	−0.0032 (9)
C1'	0.0552 (17)	0.0358 (13)	0.0406 (14)	0.0033 (12)	0.0225 (13)	0.0036 (12)
C2'	0.0499 (16)	0.0349 (13)	0.0451 (15)	−0.0015 (11)	0.0221 (13)	−0.0029 (11)
C3'	0.0508 (17)	0.0475 (16)	0.0366 (14)	−0.0064 (13)	0.0137 (12)	0.0010 (12)
C4'	0.0572 (19)	0.0431 (15)	0.0390 (15)	−0.0063 (13)	0.0053 (13)	0.0076 (12)
C5'	0.0435 (16)	0.0361 (14)	0.0447 (16)	0.0001 (11)	0.0115 (13)	0.0064 (11)
C6'	0.0432 (16)	0.0374 (14)	0.0471 (16)	−0.0017 (12)	0.0151 (13)	−0.0001 (12)
C7'	0.0462 (16)	0.0502 (16)	0.0368 (14)	−0.0023 (13)	0.0106 (12)	−0.0010 (12)
C8'	0.0515 (17)	0.0459 (15)	0.0344 (14)	0.0030 (13)	0.0139 (12)	0.0064 (12)
C9'	0.0419 (15)	0.0390 (13)	0.0363 (14)	0.0031 (11)	0.0164 (12)	0.0032 (11)
C10'	0.0405 (14)	0.0377 (13)	0.0365 (14)	0.0020 (11)	0.0136 (11)	0.0028 (11)
C61'	0.076 (2)	0.0378 (16)	0.078 (2)	−0.0075 (15)	0.0171 (19)	0.0010 (15)

Geometric parameters (Å, º)

Cl1—C2	1.762 (2)	C7—H7	0.9507
Cl2—C2	1.805 (3)	C8—H8	0.9499
Cl1'—C2'	1.770 (2)	C61—H62	0.9502
Cl2'—C2'	1.808 (3)	C61—H63	0.9501
O1—C1	1.212 (3)	C61—H61	0.9502
O6—C6	1.362 (3)	C1'—C2'	1.534 (3)
O6—C61	1.435 (4)	C1'—C9'	1.469 (3)
O1'—C1'	1.215 (3)	C2'—C3'	1.514 (4)
O6'—C6'	1.359 (3)	C3'—C4'	1.517 (5)
O6'—C61'	1.435 (4)	C4'—C10'	1.500 (3)
C1—C2	1.543 (4)	C5'—C6'	1.377 (3)
C1—C9	1.468 (3)	C5'—C10'	1.390 (3)
C2—C3	1.523 (3)	C6'—C7'	1.398 (4)
C3—C4	1.518 (3)	C7'—C8'	1.368 (4)
C4—C10	1.507 (4)	C8'—C9'	1.405 (3)
C5—C6	1.379 (4)	C9'—C10'	1.403 (3)
C5—C10	1.395 (3)	C3'—H31'	0.9489
C6—C7	1.396 (4)	C3'—H32'	0.9505
C7—C8	1.366 (4)	C4'—H41'	0.9505
C8—C9	1.409 (4)	C4'—H42'	0.9506
C9—C10	1.400 (3)	C5'—H5'	0.9501
C3—H32	0.9503	C7'—H7'	0.9504
C3—H31	0.9504	C8'—H8'	0.9497
C4—H41	0.9497	C61'—H61'	0.9499
C4—H42	0.9495	C61'—H62'	0.9505
C5—H5	0.9499	C61'—H63'	0.9509
Cl1···O1	2.911 (3)	C10'···Cl2'	3.580 (3)
Cl1···C61^i	3.440 (4)	C10'···C7'^xi	3.578 (4)
Cl1···Cl2'^ii	3.6080 (16)	C61···Cl1^iii	3.440 (4)
Cl1'···C61'^iii	3.603 (4)	C61'···Cl1'^i	3.603 (4)
Cl1'···O1'	2.909 (2)	C1···H61^vi	3.0831
Cl1'···Cl2^iii	3.6579 (16)	C5···H31'	3.0988
Cl2···O1	3.331 (3)	C5···H61	2.7402
Cl2···Cl1'^i	3.6579 (16)	C5···H63	2.7648
Cl2···C10	3.600 (3)	C5'···H61'	2.6376
Cl2···C6'^ii	3.488 (3)	C5'···H62'	2.8573
Cl2'···C10'	3.580 (3)	C9···H31	3.0608
Cl2'···C6	3.612 (3)	C9'···H32'	3.0551
Cl2'···Cl1^iv	3.6080 (16)	C61···H5	2.5039
Cl2'···O1'	3.348 (3)	C61'···H5'	2.5003
Cl1···H63^i	3.0510	H5···H41	2.4553
Cl1'···H62'^iii	3.1456	H5···C61	2.5039
Cl2···H42	2.8197	H5···Cl2'^xii	2.8744
Cl2···H5'	2.9666	H5···H61	2.2606
Cl2'···H5^v	2.8744	H5···H63	2.3377
Cl2'···H41'	2.7813	H5'···C61'	2.5003
Cl2'···H41^v	3.1424	H5'···H62'	2.4569
O1···Cl1	2.911 (3)	H5'···H42'	2.4453
O1···Cl2	3.331 (3)	H5'···H61'	2.1373
O1'···Cl1'	2.909 (2)	H5'···Cl2	2.9666
O1'···C3'^v	3.357 (4)	H7···O1^ix	2.6146
O1'···Cl2'	3.348 (3)	H7'···O1'^x	2.7276
O1···H61^vi	2.8815	H8···O6^vii	2.5187
O1···H62^i	2.8225	H8···H31^iv	2.5702
O1···H8	2.5410	H8···O1	2.5410
O1···H7^vii	2.6146	H8'···O1'	2.5433
O1···H31^iv	2.8649	H8'···O6'^viii	2.5304
O1'···H7'^viii	2.7276	H31···O1^ii	2.8649
O1'···H8'	2.5433	H31···H8^ii	2.5702
O1'···H32'^v	2.7577	H31···C9	3.0608
O6···H8^ix	2.5187	H31···O6^vi	2.7618
O6···H31^vi	2.7618	H31'···C5	3.0988
O6'···H8'^x	2.5304	H32'···O6'^xi	2.7466
O6'···H32'^xi	2.7466	H32'···O1'^xii	2.7577
C3'···O1'^xii	3.357 (4)	H32'···C9'	3.0551
C5···C8^vi	3.571 (4)	H41···Cl2'^xii	3.1424
C5···C7^vi	3.596 (4)	H41···H5	2.4553
C5'···C8'^xi	3.577 (4)	H41'···Cl2'	2.7813
C6···C10^vi	3.567 (4)	H42···Cl2	2.8197
C6···Cl2'	3.612 (3)	H42'···H5'	2.4453
C6···C9^vi	3.570 (4)	H61···C5	2.7402
C6'···C9'^xi	3.571 (4)	H61···O1^vi	2.8815
C6'···Cl2^iv	3.488 (3)	H61···C1^vi	3.0831
C7···C10^vi	3.576 (4)	H61···H5	2.2606
C7···C5^vi	3.596 (4)	H61'···H5'	2.1373
C7'···C10'^xi	3.578 (4)	H61'···C5'	2.6376
C8···C5^vi	3.571 (4)	H62···O1^iii	2.8225
C8'···C5'^xi	3.577 (4)	H62'···C5'	2.8573
C9···C6^vi	3.570 (4)	H62'···H5'	2.4569
C9'···C6'^xi	3.571 (4)	H62'···Cl1'^i	3.1456
C10···C7^vi	3.576 (4)	H63···H5	2.3377
C10···Cl2	3.600 (3)	H63···Cl1^iii	3.0510
C10···C6^vi	3.567 (4)	H63···C5	2.7648
C6—O6—C61	118.2 (2)	H61—C61—H62	109.50
C6'—O6'—C61'	117.5 (2)	O1'—C1'—C2'	120.4 (2)
O1—C1—C9	123.7 (3)	O1'—C1'—C9'	123.4 (2)
C2—C1—C9	116.1 (2)	C2'—C1'—C9'	116.12 (19)
O1—C1—C2	120.2 (2)	Cl1'—C2'—Cl2'	108.26 (15)
Cl1—C2—Cl2	108.24 (14)	Cl1'—C2'—C1'	111.38 (17)
Cl1—C2—C3	109.61 (16)	Cl1'—C2'—C3'	109.64 (18)
Cl2—C2—C1	104.85 (16)	Cl2'—C2'—C1'	104.99 (18)
Cl1—C2—C1	111.31 (18)	Cl2'—C2'—C3'	109.94 (19)
C1—C2—C3	112.3 (2)	C1'—C2'—C3'	112.5 (2)
Cl2—C2—C3	110.33 (19)	C2'—C3'—C4'	111.3 (2)
C2—C3—C4	111.71 (19)	C3'—C4'—C10'	113.0 (2)
C3—C4—C10	112.6 (2)	C6'—C5'—C10'	120.8 (2)
C6—C5—C10	120.4 (2)	O6'—C6'—C5'	124.6 (2)
O6—C6—C5	124.0 (2)	O6'—C6'—C7'	115.2 (2)
O6—C6—C7	115.4 (2)	C5'—C6'—C7'	120.2 (2)
C5—C6—C7	120.5 (2)	C6'—C7'—C8'	119.6 (2)
C6—C7—C8	119.5 (3)	C7'—C8'—C9'	121.1 (2)
C7—C8—C9	121.1 (2)	C1'—C9'—C8'	119.1 (2)
C1—C9—C10	122.2 (2)	C1'—C9'—C10'	122.0 (2)
C8—C9—C10	119.1 (2)	C8'—C9'—C10'	119.0 (2)
C1—C9—C8	118.7 (2)	C4'—C10'—C5'	119.3 (2)
C4—C10—C9	121.7 (2)	C4'—C10'—C9'	121.3 (2)
C5—C10—C9	119.4 (2)	C5'—C10'—C9'	119.4 (2)
C4—C10—C5	118.9 (2)	C2'—C3'—H31'	109.11
C2—C3—H32	108.98	C2'—C3'—H32'	109.01
C4—C3—H31	108.87	C4'—C3'—H31'	108.99
C4—C3—H32	108.83	C4'—C3'—H32'	108.96
H31—C3—H32	109.47	H31'—C3'—H32'	109.43
C2—C3—H31	108.96	C3'—C4'—H41'	108.55
C3—C4—H41	108.68	C3'—C4'—H42'	108.54
C3—C4—H42	108.65	C10'—C4'—H41'	108.59
C10—C4—H42	108.68	C10'—C4'—H42'	108.60
H41—C4—H42	109.46	H41'—C4'—H42'	109.55
C10—C4—H41	108.71	C6'—C5'—H5'	119.63
C6—C5—H5	119.71	C10'—C5'—H5'	119.62
C10—C5—H5	119.84	C6'—C7'—H7'	120.30
C8—C7—H7	120.20	C8'—C7'—H7'	120.09
C6—C7—H7	120.32	C7'—C8'—H8'	119.48
C7—C8—H8	119.42	C9'—C8'—H8'	119.45
C9—C8—H8	119.49	O6'—C61'—H61'	109.48
O6—C61—H62	109.49	O6'—C61'—H62'	109.48
O6—C61—H63	109.44	O6'—C61'—H63'	109.47
O6—C61—H61	109.47	H61'—C61'—H62'	109.49
H61—C61—H63	109.50	H61'—C61'—H63'	109.41
H62—C61—H63	109.43	H62'—C61'—H63'	109.50
C61—O6—C6—C5	6.0 (4)	C1—C9—C10—C4	0.7 (4)
C61—O6—C6—C7	−174.2 (3)	C1—C9—C10—C5	−179.7 (2)
C61'—O6'—C6'—C5'	6.5 (4)	O1'—C1'—C2'—C3'	−147.2 (3)
C61'—O6'—C6'—C7'	−173.7 (3)	C9'—C1'—C2'—Cl1'	157.6 (2)
C9—C1—C2—C3	33.3 (3)	C9'—C1'—C2'—C3'	34.1 (4)
O1—C1—C9—C8	−4.1 (4)	O1'—C1'—C9'—C8'	−4.8 (5)
C9—C1—C2—Cl2	−86.5 (2)	C9'—C1'—C2'—Cl2'	−85.4 (3)
O1—C1—C2—Cl1	−24.9 (3)	O1'—C1'—C2'—Cl2'	93.3 (3)
O1—C1—C2—Cl2	91.9 (3)	C2'—C1'—C9'—C10'	−6.9 (4)
C2—C1—C9—C10	−6.4 (3)	O1'—C1'—C2'—Cl1'	−23.6 (4)
O1—C1—C9—C10	175.3 (3)	O1'—C1'—C9'—C10'	174.4 (3)
C2—C1—C9—C8	174.3 (2)	C2'—C1'—C9'—C8'	173.9 (3)
C9—C1—C2—Cl1	156.68 (18)	Cl1'—C2'—C3'—C4'	−179.8 (2)
O1—C1—C2—C3	−148.3 (2)	Cl2'—C2'—C3'—C4'	61.3 (3)
C1—C2—C3—C4	−54.8 (3)	C1'—C2'—C3'—C4'	−55.3 (3)
Cl2—C2—C3—C4	61.7 (3)	C2'—C3'—C4'—C10'	49.2 (3)
Cl1—C2—C3—C4	−179.2 (2)	C3'—C4'—C10'—C9'	−22.6 (4)
C2—C3—C4—C10	48.9 (3)	C3'—C4'—C10'—C5'	157.8 (3)
C3—C4—C10—C9	−22.3 (3)	C6'—C5'—C10'—C4'	−179.9 (3)
C3—C4—C10—C5	158.2 (2)	C10'—C5'—C6'—C7'	−0.9 (4)
C10—C5—C6—C7	−1.0 (4)	C10'—C5'—C6'—O6'	178.9 (3)
C6—C5—C10—C4	−179.8 (2)	C6'—C5'—C10'—C9'	0.5 (4)
C6—C5—C10—C9	0.7 (4)	O6'—C6'—C7'—C8'	−178.8 (3)
C10—C5—C6—O6	178.8 (2)	C5'—C6'—C7'—C8'	0.9 (4)
C5—C6—C7—C8	1.1 (4)	C6'—C7'—C8'—C9'	−0.6 (5)
O6—C6—C7—C8	−178.7 (2)	C7'—C8'—C9'—C10'	0.2 (4)
C6—C7—C8—C9	−0.8 (4)	C7'—C8'—C9'—C1'	179.4 (3)
C7—C8—C9—C10	0.4 (4)	C1'—C9'—C10'—C4'	1.1 (4)
C7—C8—C9—C1	179.8 (2)	C1'—C9'—C10'—C5'	−179.3 (3)
C8—C9—C10—C5	−0.4 (4)	C8'—C9'—C10'—C4'	−179.7 (3)
C8—C9—C10—C4	−179.9 (2)	C8'—C9'—C10'—C5'	−0.1 (4)

Symmetry codes: (i) x, y+1, z; (ii) x, −y+3/2, z−1/2; (iii) x, y−1, z; (iv) x, −y+3/2, z+1/2; (v) x, −y+1/2, z+1/2; (vi) −x+1, −y+1, −z+1; (vii) −x+1, y+1/2, −z+3/2; (viii) −x+2, y−1/2, −z+5/2; (ix) −x+1, y−1/2, −z+3/2; (x) −x+2, y+1/2, −z+5/2; (xi) −x+2, −y+1, −z+2; (xii) x, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O6^vii	0.95	2.52	3.438 (3)	163
C8′—H8′···O6′^viii	0.95	2.53	3.445 (3)	162
C4′—H41′···Cl2′	0.95	2.78	3.126 (3)	102
C4—H42···Cl2	0.95	2.82	3.154 (3)	102

Symmetry codes: (vii) −x+1, y+1/2, −z+3/2; (viii) −x+2, y−1/2, −z+5/2.