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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802018688/tk6083sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802018688/tk6083Isup2.hkl
Contains datablock I

CCDC reference: 200767

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








Computing details top

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 top
Crystal data top
C11H10Cl2O2F(000) = 1008
Mr = 245.09Dx = 1.498 Mg m3
Monoclinic, P21/cMelting point = 358–360 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71069 Å
a = 17.569 (5) ÅCell parameters from 25 reflections
b = 10.745 (3) Åθ = 12.6–17.1°
c = 12.239 (4) ŵ = 0.57 mm1
β = 109.83 (2)°T = 295 K
V = 2173.5 (12) Å3Prismatic, colorless
Z = 80.30 × 0.30 × 0.14 mm
Data collection top
Rigaku AFC7R
diffractometer
Rint = 0.040
Radiation source: Rigaku rotating anodeθmax = 27.5°, θmin = 2.6°
Graphite monochromatorh = 1022
ω–2θ scansk = 136
6026 measured reflectionsl = 1514
4967 independent reflections3 standard reflections every 150 reflections
2849 reflections with I > 2σ(I) intensity decay: 4.8%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-atom parameters not refined
S = 0.99 w = 1/[σ2(Fo2) + (0.0484P)2 + 0.7378P]
where P = (Fo2 + 2Fc2)/3
4967 reflections(Δ/σ)max < 0.001
271 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.30 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cl10.68166 (6)0.95196 (7)0.51981 (8)0.0640 (3)
Cl20.78694 (5)0.77739 (7)0.68095 (7)0.0594 (3)
O10.60019 (14)0.84924 (18)0.67073 (19)0.0619 (8)
O60.53343 (12)0.27044 (17)0.64489 (19)0.0530 (7)
C10.62726 (16)0.7666 (2)0.6273 (2)0.0396 (8)
C20.68993 (16)0.7964 (2)0.5681 (2)0.0409 (8)
C30.68292 (17)0.7093 (2)0.4670 (2)0.0441 (9)
C40.68842 (17)0.5737 (2)0.5037 (2)0.0440 (9)
C50.61036 (16)0.4195 (2)0.5766 (2)0.0403 (8)
C60.55988 (16)0.3882 (2)0.6374 (2)0.0405 (8)
C70.53218 (17)0.4792 (3)0.6962 (2)0.0431 (9)
C80.55439 (16)0.6004 (2)0.6916 (2)0.0412 (8)
C90.60559 (15)0.6349 (2)0.6296 (2)0.0362 (8)
C100.63345 (15)0.5430 (2)0.5714 (2)0.0353 (8)
C610.5657 (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)
H50.629500.356500.538000.0480*
H70.498100.457100.739100.0520*
H80.535000.662400.730900.0490*
H310.632300.722900.407500.0530*
H320.725500.726900.437900.0530*
H410.673900.523100.436100.0530*
H420.742600.556200.550800.0530*
H610.552000.183900.514500.0740*
H620.543600.094000.609000.0740*
H630.622900.168900.631100.0740*
H5'0.875400.665800.910800.0510*
H7'0.999300.561401.241400.0540*
H8'0.958700.357701.195300.0530*
H31'0.775500.299400.714100.0540*
H32'0.868300.299300.777900.0540*
H41'0.759300.470900.810300.0590*
H42'0.830000.500900.765400.0590*
H61'0.948000.829400.962100.0800*
H62'0.884000.860501.019600.0800*
H63'0.968600.923201.064400.0800*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0920 (6)0.0361 (4)0.0747 (5)0.0056 (4)0.0424 (5)0.0143 (4)
Cl20.0501 (4)0.0584 (5)0.0615 (5)0.0076 (4)0.0083 (4)0.0027 (4)
O10.0863 (16)0.0385 (11)0.0788 (16)0.0008 (10)0.0515 (13)0.0083 (10)
O60.0571 (12)0.0354 (10)0.0754 (14)0.0037 (9)0.0341 (11)0.0023 (9)
C10.0476 (16)0.0363 (13)0.0376 (14)0.0042 (12)0.0179 (12)0.0006 (11)
C20.0465 (16)0.0330 (13)0.0440 (15)0.0017 (11)0.0162 (12)0.0040 (11)
C30.0512 (16)0.0450 (15)0.0443 (15)0.0011 (12)0.0270 (13)0.0023 (12)
C40.0482 (16)0.0402 (14)0.0519 (16)0.0019 (12)0.0278 (14)0.0050 (12)
C50.0407 (15)0.0342 (13)0.0485 (16)0.0019 (11)0.0182 (12)0.0048 (11)
C60.0394 (15)0.0373 (14)0.0444 (15)0.0014 (11)0.0137 (12)0.0020 (11)
C70.0452 (16)0.0465 (16)0.0449 (15)0.0034 (12)0.0248 (13)0.0006 (12)
C80.0477 (16)0.0417 (14)0.0384 (14)0.0005 (12)0.0202 (12)0.0061 (11)
C90.0398 (14)0.0345 (13)0.0344 (13)0.0006 (10)0.0128 (11)0.0033 (10)
C100.0359 (14)0.0366 (13)0.0349 (13)0.0003 (11)0.0141 (11)0.0013 (11)
C610.069 (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) top
Cl1—C21.762 (2)C7—H70.9507
Cl2—C21.805 (3)C8—H80.9499
Cl1'—C2'1.770 (2)C61—H620.9502
Cl2'—C2'1.808 (3)C61—H630.9501
O1—C11.212 (3)C61—H610.9502
O6—C61.362 (3)C1'—C2'1.534 (3)
O6—C611.435 (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—C21.543 (4)C5'—C6'1.377 (3)
C1—C91.468 (3)C5'—C10'1.390 (3)
C2—C31.523 (3)C6'—C7'1.398 (4)
C3—C41.518 (3)C7'—C8'1.368 (4)
C4—C101.507 (4)C8'—C9'1.405 (3)
C5—C61.379 (4)C9'—C10'1.403 (3)
C5—C101.395 (3)C3'—H31'0.9489
C6—C71.396 (4)C3'—H32'0.9505
C7—C81.366 (4)C4'—H41'0.9505
C8—C91.409 (4)C4'—H42'0.9506
C9—C101.400 (3)C5'—H5'0.9501
C3—H320.9503C7'—H7'0.9504
C3—H310.9504C8'—H8'0.9497
C4—H410.9497C61'—H61'0.9499
C4—H420.9495C61'—H62'0.9505
C5—H50.9499C61'—H63'0.9509
Cl1···O12.911 (3)C10'···Cl2'3.580 (3)
Cl1···C61i3.440 (4)C10'···C7'xi3.578 (4)
Cl1···Cl2'ii3.6080 (16)C61···Cl1iii3.440 (4)
Cl1'···C61'iii3.603 (4)C61'···Cl1'i3.603 (4)
Cl1'···O1'2.909 (2)C1···H61vi3.0831
Cl1'···Cl2iii3.6579 (16)C5···H31'3.0988
Cl2···O13.331 (3)C5···H612.7402
Cl2···Cl1'i3.6579 (16)C5···H632.7648
Cl2···C103.600 (3)C5'···H61'2.6376
Cl2···C6'ii3.488 (3)C5'···H62'2.8573
Cl2'···C10'3.580 (3)C9···H313.0608
Cl2'···C63.612 (3)C9'···H32'3.0551
Cl2'···Cl1iv3.6080 (16)C61···H52.5039
Cl2'···O1'3.348 (3)C61'···H5'2.5003
Cl1···H63i3.0510H5···H412.4553
Cl1'···H62'iii3.1456H5···C612.5039
Cl2···H422.8197H5···Cl2'xii2.8744
Cl2···H5'2.9666H5···H612.2606
Cl2'···H5v2.8744H5···H632.3377
Cl2'···H41'2.7813H5'···C61'2.5003
Cl2'···H41v3.1424H5'···H62'2.4569
O1···Cl12.911 (3)H5'···H42'2.4453
O1···Cl23.331 (3)H5'···H61'2.1373
O1'···Cl1'2.909 (2)H5'···Cl22.9666
O1'···C3'v3.357 (4)H7···O1ix2.6146
O1'···Cl2'3.348 (3)H7'···O1'x2.7276
O1···H61vi2.8815H8···O6vii2.5187
O1···H62i2.8225H8···H31iv2.5702
O1···H82.5410H8···O12.5410
O1···H7vii2.6146H8'···O1'2.5433
O1···H31iv2.8649H8'···O6'viii2.5304
O1'···H7'viii2.7276H31···O1ii2.8649
O1'···H8'2.5433H31···H8ii2.5702
O1'···H32'v2.7577H31···C93.0608
O6···H8ix2.5187H31···O6vi2.7618
O6···H31vi2.7618H31'···C53.0988
O6'···H8'x2.5304H32'···O6'xi2.7466
O6'···H32'xi2.7466H32'···O1'xii2.7577
C3'···O1'xii3.357 (4)H32'···C9'3.0551
C5···C8vi3.571 (4)H41···Cl2'xii3.1424
C5···C7vi3.596 (4)H41···H52.4553
C5'···C8'xi3.577 (4)H41'···Cl2'2.7813
C6···C10vi3.567 (4)H42···Cl22.8197
C6···Cl2'3.612 (3)H42'···H5'2.4453
C6···C9vi3.570 (4)H61···C52.7402
C6'···C9'xi3.571 (4)H61···O1vi2.8815
C6'···Cl2iv3.488 (3)H61···C1vi3.0831
C7···C10vi3.576 (4)H61···H52.2606
C7···C5vi3.596 (4)H61'···H5'2.1373
C7'···C10'xi3.578 (4)H61'···C5'2.6376
C8···C5vi3.571 (4)H62···O1iii2.8225
C8'···C5'xi3.577 (4)H62'···C5'2.8573
C9···C6vi3.570 (4)H62'···H5'2.4569
C9'···C6'xi3.571 (4)H62'···Cl1'i3.1456
C10···C7vi3.576 (4)H63···H52.3377
C10···Cl23.600 (3)H63···Cl1iii3.0510
C10···C6vi3.567 (4)H63···C52.7648
C6—O6—C61118.2 (2)H61—C61—H62109.50
C6'—O6'—C61'117.5 (2)O1'—C1'—C2'120.4 (2)
O1—C1—C9123.7 (3)O1'—C1'—C9'123.4 (2)
C2—C1—C9116.1 (2)C2'—C1'—C9'116.12 (19)
O1—C1—C2120.2 (2)Cl1'—C2'—Cl2'108.26 (15)
Cl1—C2—Cl2108.24 (14)Cl1'—C2'—C1'111.38 (17)
Cl1—C2—C3109.61 (16)Cl1'—C2'—C3'109.64 (18)
Cl2—C2—C1104.85 (16)Cl2'—C2'—C1'104.99 (18)
Cl1—C2—C1111.31 (18)Cl2'—C2'—C3'109.94 (19)
C1—C2—C3112.3 (2)C1'—C2'—C3'112.5 (2)
Cl2—C2—C3110.33 (19)C2'—C3'—C4'111.3 (2)
C2—C3—C4111.71 (19)C3'—C4'—C10'113.0 (2)
C3—C4—C10112.6 (2)C6'—C5'—C10'120.8 (2)
C6—C5—C10120.4 (2)O6'—C6'—C5'124.6 (2)
O6—C6—C5124.0 (2)O6'—C6'—C7'115.2 (2)
O6—C6—C7115.4 (2)C5'—C6'—C7'120.2 (2)
C5—C6—C7120.5 (2)C6'—C7'—C8'119.6 (2)
C6—C7—C8119.5 (3)C7'—C8'—C9'121.1 (2)
C7—C8—C9121.1 (2)C1'—C9'—C8'119.1 (2)
C1—C9—C10122.2 (2)C1'—C9'—C10'122.0 (2)
C8—C9—C10119.1 (2)C8'—C9'—C10'119.0 (2)
C1—C9—C8118.7 (2)C4'—C10'—C5'119.3 (2)
C4—C10—C9121.7 (2)C4'—C10'—C9'121.3 (2)
C5—C10—C9119.4 (2)C5'—C10'—C9'119.4 (2)
C4—C10—C5118.9 (2)C2'—C3'—H31'109.11
C2—C3—H32108.98C2'—C3'—H32'109.01
C4—C3—H31108.87C4'—C3'—H31'108.99
C4—C3—H32108.83C4'—C3'—H32'108.96
H31—C3—H32109.47H31'—C3'—H32'109.43
C2—C3—H31108.96C3'—C4'—H41'108.55
C3—C4—H41108.68C3'—C4'—H42'108.54
C3—C4—H42108.65C10'—C4'—H41'108.59
C10—C4—H42108.68C10'—C4'—H42'108.60
H41—C4—H42109.46H41'—C4'—H42'109.55
C10—C4—H41108.71C6'—C5'—H5'119.63
C6—C5—H5119.71C10'—C5'—H5'119.62
C10—C5—H5119.84C6'—C7'—H7'120.30
C8—C7—H7120.20C8'—C7'—H7'120.09
C6—C7—H7120.32C7'—C8'—H8'119.48
C7—C8—H8119.42C9'—C8'—H8'119.45
C9—C8—H8119.49O6'—C61'—H61'109.48
O6—C61—H62109.49O6'—C61'—H62'109.48
O6—C61—H63109.44O6'—C61'—H63'109.47
O6—C61—H61109.47H61'—C61'—H62'109.49
H61—C61—H63109.50H61'—C61'—H63'109.41
H62—C61—H63109.43H62'—C61'—H63'109.50
C61—O6—C6—C56.0 (4)C1—C9—C10—C40.7 (4)
C61—O6—C6—C7174.2 (3)C1—C9—C10—C5179.7 (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—C333.3 (3)C9'—C1'—C2'—C3'34.1 (4)
O1—C1—C9—C84.1 (4)O1'—C1'—C9'—C8'4.8 (5)
C9—C1—C2—Cl286.5 (2)C9'—C1'—C2'—Cl2'85.4 (3)
O1—C1—C2—Cl124.9 (3)O1'—C1'—C2'—Cl2'93.3 (3)
O1—C1—C2—Cl291.9 (3)C2'—C1'—C9'—C10'6.9 (4)
C2—C1—C9—C106.4 (3)O1'—C1'—C2'—Cl1'23.6 (4)
O1—C1—C9—C10175.3 (3)O1'—C1'—C9'—C10'174.4 (3)
C2—C1—C9—C8174.3 (2)C2'—C1'—C9'—C8'173.9 (3)
C9—C1—C2—Cl1156.68 (18)Cl1'—C2'—C3'—C4'179.8 (2)
O1—C1—C2—C3148.3 (2)Cl2'—C2'—C3'—C4'61.3 (3)
C1—C2—C3—C454.8 (3)C1'—C2'—C3'—C4'55.3 (3)
Cl2—C2—C3—C461.7 (3)C2'—C3'—C4'—C10'49.2 (3)
Cl1—C2—C3—C4179.2 (2)C3'—C4'—C10'—C9'22.6 (4)
C2—C3—C4—C1048.9 (3)C3'—C4'—C10'—C5'157.8 (3)
C3—C4—C10—C922.3 (3)C6'—C5'—C10'—C4'179.9 (3)
C3—C4—C10—C5158.2 (2)C10'—C5'—C6'—C7'0.9 (4)
C10—C5—C6—C71.0 (4)C10'—C5'—C6'—O6'178.9 (3)
C6—C5—C10—C4179.8 (2)C6'—C5'—C10'—C9'0.5 (4)
C6—C5—C10—C90.7 (4)O6'—C6'—C7'—C8'178.8 (3)
C10—C5—C6—O6178.8 (2)C5'—C6'—C7'—C8'0.9 (4)
C5—C6—C7—C81.1 (4)C6'—C7'—C8'—C9'0.6 (5)
O6—C6—C7—C8178.7 (2)C7'—C8'—C9'—C10'0.2 (4)
C6—C7—C8—C90.8 (4)C7'—C8'—C9'—C1'179.4 (3)
C7—C8—C9—C100.4 (4)C1'—C9'—C10'—C4'1.1 (4)
C7—C8—C9—C1179.8 (2)C1'—C9'—C10'—C5'179.3 (3)
C8—C9—C10—C50.4 (4)C8'—C9'—C10'—C4'179.7 (3)
C8—C9—C10—C4179.9 (2)C8'—C9'—C10'—C5'0.1 (4)
Symmetry codes: (i) x, y+1, z; (ii) x, y+3/2, z1/2; (iii) x, y1, 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, y1/2, z+5/2; (ix) x+1, y1/2, z+3/2; (x) x+2, y+1/2, z+5/2; (xi) x+2, y+1, z+2; (xii) x, y+1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O6vii0.952.523.438 (3)163
C8—H8···O6viii0.952.533.445 (3)162
C4—H41···Cl20.952.783.126 (3)102
C4—H42···Cl20.952.823.154 (3)102
Symmetry codes: (vii) x+1, y+1/2, z+3/2; (viii) x+2, y1/2, z+5/2.
 

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