[2.2]Dihydro­isobenzothio­phenophane

Kannan, A.; Dix, I.; Hopf, H.; Jones, P.G.

doi:10.1107/S160053680502979X

[2.2]Dihydroisobenzothiophenophane

A. Kannan, I. Dix, H. Hopf and P. G. Jones

In the unit cell of the title compound, 1¹,1³,4¹,4³-tetrahydro-1,4(4,7)-di(benzo[c]thiophena)cyclohexaphane, C₂₀H₂₀S₂, there are four independent but closely similar molecules, each with crystallographic inversion symmetry. The packing is interpreted in terms of layers formed via C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680502979X/bt6742sup1.cif Contains datablocks 2, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680502979X/bt67422sup2.hkl Contains datablock 2

CCDC reference: 289645

checkCIF report

Key indicators

Single-crystal X-ray study
T = 143 K
Mean (C-C) = 0.003 Å
R factor = 0.044
wR factor = 0.107
Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT725_ALERT_1_A D-H     Calc     0.99000, Rep     1.08000 Dev...       0.09 Ang.
              C18" -H18F    1.555   1.555
PLAT725_ALERT_1_A D-H     Calc     0.99000, Rep     1.08000 Dev...       0.09 Ang.
              C18  -H18A    1.555   1.555
PLAT725_ALERT_1_A D-H     Calc     0.99000, Rep     1.08000 Dev...       0.09 Ang.
              C17' -H17C    1.555   1.555
PLAT725_ALERT_1_A D-H     Calc     0.99000, Rep     1.08000 Dev...       0.09 Ang.
              C1#  -H10#    1.555   1.555

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        S1*
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2"2   ..  S1'     ..       2.95 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9"2   ..  S1'     ..       3.02 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9*1   ..  S1"     ..       2.96 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7     ..  S1#     ..       2.94 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9'1   ..  S1      ..       3.07 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8"    ..  S1      ..       3.08 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8*    ..  S1'     ..       3.10 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H17B   ..  S1#     ..       3.07 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2*2   ..  CG2     ..       2.98 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C1#    ..  CG2     ..       4.04 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         25

   4 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  13 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   4 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
   0 ALERT type 3 Indicator that the structure quality may be low
  12 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: DIF4 (Stoe & Cie, 1992); cell refinement: DIF4; data reduction: REDU4 (Stoe & Cie, 1992); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

1¹,1³,4¹,4³-Tetrahydro-1,4(4,7)-di(benzo[c]thiophena)cyclohexaphane top

Crystal data top

C₂₀H₂₀S₂	Z = 4
M_r = 324.48	F(000) = 688
Triclinic, P1	D_x = 1.379 Mg m⁻³
a = 10.088 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.182 (2) Å	Cell parameters from 52 reflections
c = 15.247 (2) Å	θ = 10–11.5°
α = 86.53 (2)°	µ = 0.33 mm⁻¹
β = 88.44 (2)°	T = 143 K
γ = 89.81 (2)°	Prism, colourless
V = 1562.7 (5) Å³	0.6 × 0.35 × 0.3 mm

Data collection top

Stoe STADI-4 diffractometer	R_int = 0.026
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 3.1°
Graphite monochromator	h = −12→6
θ/ω scans	k = −12→12
9570 measured reflections	l = −18→18
5496 independent reflections	3 standard reflections every 60 min
4469 reflections with I > 2σ(I)	intensity decay: 2%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0354P)² + 1.5793P] where P = (F_o² + 2F_c²)/3
5496 reflections	(Δ/σ)_max < 0.001
397 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

8.2417 (0.0082) x + 5.8422 (0.0102) y - 0.3478 (0.0216) z = 5.6479 (0.0045)

* 0.0027 (0.0011) C4 * -0.0027 (0.0011) C5 * 0.0027 (0.0011) C7 * -0.0027 (0.0011) C8 - 0.1586 (0.0035) C3 - 0.1542 (0.0034) C6

Rms deviation of fitted atoms = 0.0027

8.2191 (0.0066) x + 5.8387 (0.0079) y - 0.6877 (0.0161) z = 5.6250 (0.0033)

Angle to previous plane (with approximate e.s.d.) = 1.28 (0.15)

* -0.0121 (0.0016) C4 * 0.0081 (0.0015) C5 * 0.0094 (0.0014) C17 * -0.0010 (0.0014) C18 * -0.0044 (0.0012) S1

Rms deviation of fitted atoms = 0.0080

6.2896 (0.0095) x + 7.7161 (0.0099) y - 2.0906 (0.0215) z = 4.4340 (0.0126)

Angle to previous plane (with approximate e.s.d.) = 16.31 (0.14)

* 0.0017 (0.0012) C4' * -0.0017 (0.0012) C5' * 0.0017 (0.0012) C7' * -0.0017 (0.0012) C8' 0.1581 (0.0035) C3' 0.1519 (0.0035) C6'

Rms deviation of fitted atoms = 0.0017

6.2499 (0.0075) x + 7.7221 (0.0076) y - 2.2399 (0.0160) z = 4.3489 (0.0087)

Angle to previous plane (with approximate e.s.d.) = 0.60 (0.17)

* 0.0006 (0.0016) C4' * 0.0049 (0.0016) C5' * -0.0047 (0.0014) C17' * -0.0069 (0.0014) C18' * 0.0061 (0.0012) S1'

Rms deviation of fitted atoms = 0.0051

- 8.0582 (0.0085) x + 6.0346 (0.0100) y + 1.5430 (0.0213) z = 1.4871 (0.0051)

Angle to previous plane (with approximate e.s.d.) = 86.39 (0.07)

* -0.0045 (0.0011) C4" * 0.0045 (0.0011) C5" * -0.0045 (0.0011) C7" * 0.0045 (0.0011) C8" 0.1614 (0.0033) C3" 0.1571 (0.0034) C6"

Rms deviation of fitted atoms = 0.0045

- 8.0939 (0.0068) x + 5.9333 (0.0079) y + 1.9841 (0.0166) z = 1.4685 (0.0030)

Angle to previous plane (with approximate e.s.d.) = 1.81 (0.16)

* 0.0036 (0.0016) C4" * -0.0105 (0.0015) C5" * 0.0036 (0.0014) C17" * 0.0110 (0.0014) C18" * -0.0077 (0.0012) S1"

Rms deviation of fitted atoms = 0.0080

5.5183 (0.0107) x - 8.5054 (0.0076) y - 0.6510 (0.0211) z = 3.6608 (0.0185)

Angle to previous plane (with approximate e.s.d.) = 21.62 (0.13)

* -0.0031 (0.0011) C4* * 0.0031 (0.0011) C5* * -0.0031 (0.0011) C7* * 0.0031 (0.0011) C8* 0.1622 (0.0034) C3* 0.1588 (0.0034) C6*

Rms deviation of fitted atoms = 0.0031

5.5258 (0.0084) x - 8.4981 (0.0063) y - 0.2217 (0.0163) z = 3.9049 (0.0137)

Angle to previous plane (with approximate e.s.d.) = 1.61 (0.15)

* 0.0103 (0.0016) C4* * -0.0138 (0.0015) C5* * -0.0024 (0.0014) C17* * 0.0099 (0.0013) C18* * -0.0039 (0.0012) S1*

Rms deviation of fitted atoms = 0.0091

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

	x	y	z	U_iso*/U_eq
S1	0.46742 (7)	0.32035 (7)	0.13319 (5)	0.04091 (19)
C2	0.6735 (3)	−0.1030 (3)	0.13715 (17)	0.0384 (6)
H2A	0.7013	−0.0607	0.1904	0.046*
H2B	0.7408	−0.1703	0.1235	0.046*
C3	0.6690 (2)	−0.0005 (2)	0.06142 (16)	0.0272 (5)
C4	0.6035 (2)	0.1200 (2)	0.06956 (15)	0.0254 (5)
C5	0.5516 (2)	0.1879 (2)	−0.00326 (15)	0.0251 (5)
C6	0.5648 (2)	0.1384 (2)	−0.08687 (15)	0.0275 (5)
C7	0.6555 (2)	0.0368 (2)	−0.09597 (16)	0.0298 (5)
H7	0.6831	0.0138	−0.1531	0.036*
C8	0.7063 (2)	−0.0315 (2)	−0.02310 (16)	0.0290 (5)
H8	0.7679	−0.1009	−0.0311	0.035*
C9	0.4655 (3)	0.1730 (3)	−0.15685 (16)	0.0387 (6)
H9A	0.5017	0.1468	−0.2142	0.046*
H9B	0.4522	0.2695	−0.1612	0.046*
C17	0.5727 (3)	0.1773 (2)	0.15669 (16)	0.0327 (6)
H17A	0.6554	0.2037	0.1844	0.039*
H17B	0.5259	0.1120	0.1970	0.039*
C18	0.4681 (3)	0.3061 (2)	0.01518 (16)	0.0318 (6)
H18A	0.3766	0.2944	−0.0050	0.038*
H18B	0.5061	0.3863	−0.0156	0.038*
S1'	0.16487 (7)	0.53926 (7)	0.37484 (4)	0.04050 (19)
C2'	0.3479 (3)	0.5699 (3)	0.65659 (16)	0.0382 (6)
H2'1	0.3785	0.5411	0.7158	0.046*
H2'2	0.2524	0.5917	0.6619	0.046*
C3'	0.3662 (2)	0.4581 (2)	0.59600 (15)	0.0282 (5)
C4'	0.3074 (2)	0.4634 (2)	0.51371 (15)	0.0250 (5)
C5'	0.3636 (2)	0.3986 (2)	0.44486 (15)	0.0251 (5)
C6'	0.4808 (2)	0.3258 (2)	0.45561 (16)	0.0280 (5)
C7'	0.5197 (2)	0.2980 (2)	0.54149 (17)	0.0305 (6)
H7'	0.5863	0.2336	0.5530	0.037*
C8'	0.4627 (3)	0.3627 (2)	0.61063 (16)	0.0317 (6)
H8'	0.4902	0.3413	0.6689	0.038*
C9'	0.5725 (3)	0.3027 (3)	0.37834 (18)	0.0374 (6)
H9'1	0.5198	0.2713	0.3300	0.045*
H9'2	0.6365	0.2326	0.3957	0.045*
C17'	0.1912 (2)	0.5504 (3)	0.49131 (16)	0.0322 (6)
H17C	0.2101	0.6424	0.5044	0.039*
H17D	0.1113	0.5203	0.5260	0.039*
C18'	0.2994 (3)	0.4236 (3)	0.35732 (16)	0.0323 (6)
H18C	0.2647	0.3406	0.3364	0.039*
H18D	0.3644	0.4613	0.3130	0.039*
S1"	−0.02945 (8)	0.15950 (8)	0.13919 (5)	0.0492 (2)
C2"	0.1827 (3)	0.5802 (3)	0.13048 (17)	0.0345 (6)
H2"1	0.2506	0.6478	0.1136	0.041*
H2"2	0.2129	0.5297	0.1838	0.041*
C3"	0.1718 (2)	0.4881 (2)	0.05693 (15)	0.0261 (5)
C4"	0.1046 (2)	0.3677 (2)	0.06925 (15)	0.0249 (5)
C5"	0.0478 (2)	0.3112 (2)	−0.00086 (15)	0.0257 (5)
C6"	0.0577 (2)	0.3714 (2)	−0.08575 (15)	0.0269 (5)
C7"	0.1503 (2)	0.4717 (2)	−0.09934 (16)	0.0289 (5)
H7"	0.1758	0.5012	−0.1576	0.035*
C8"	0.2058 (2)	0.5295 (2)	−0.02908 (16)	0.0285 (5)
H8"	0.2683	0.5986	−0.0400	0.034*
C9"	−0.0465 (3)	0.3486 (3)	−0.15289 (17)	0.0367 (6)
H9"1	−0.0621	0.2529	−0.1549	0.044*
H9"2	−0.0132	0.3820	−0.2117	0.044*
C17"	0.0765 (3)	0.2995 (3)	0.15819 (17)	0.0371 (6)
H17E	0.0307	0.3600	0.1976	0.045*
H17F	0.1600	0.2693	0.1855	0.045*
C18"	−0.0368 (3)	0.1919 (2)	0.02156 (17)	0.0335 (6)
H18E	−0.0025	0.1156	−0.0094	0.040*
H18F	−0.1294	0.2089	0.0041	0.040*
S1*	0.68145 (8)	−0.03311 (8)	0.65854 (5)	0.0496 (2)
C2*	1.1154 (3)	0.1545 (3)	0.63405 (17)	0.0354 (6)
H2*1	1.0766	0.1763	0.6917	0.043*
H2*2	1.1844	0.2209	0.6169	0.043*
C3*	1.0081 (2)	0.1613 (2)	0.56640 (16)	0.0277 (5)
C4*	0.8851 (2)	0.0996 (2)	0.58273 (15)	0.0252 (5)
C5*	0.8128 (2)	0.0572 (2)	0.51405 (15)	0.0249 (5)
C6*	0.8598 (2)	0.0761 (2)	0.42674 (15)	0.0262 (5)
C7*	0.9640 (2)	0.1639 (2)	0.41142 (16)	0.0290 (5)
H7*	0.9855	0.1960	0.3530	0.035*
C8*	1.0372 (2)	0.2054 (2)	0.48019 (16)	0.0277 (5)
H8*	1.1085	0.2651	0.4681	0.033*
C9*	0.8179 (3)	−0.0129 (3)	0.35679 (16)	0.0333 (6)
H9*1	0.8418	0.0290	0.2982	0.040*
H9*2	0.7203	−0.0230	0.3603	0.040*
C17*	0.8300 (3)	0.0629 (3)	0.67342 (16)	0.0355 (6)
H17G	0.8079	0.1428	0.7048	0.043*
H17H	0.8953	0.0102	0.7079	0.043*
C18*	0.6925 (2)	−0.0244 (2)	0.53958 (16)	0.0313 (6)
H18G	0.7020	−0.1137	0.5177	0.038*
H18H	0.6119	0.0171	0.5146	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0449 (4)	0.0421 (4)	0.0372 (4)	0.0133 (3)	0.0002 (3)	−0.0154 (3)
C2	0.0445 (16)	0.0372 (15)	0.0349 (14)	0.0138 (12)	−0.0169 (12)	−0.0073 (11)
C3	0.0189 (12)	0.0290 (13)	0.0347 (13)	0.0007 (10)	−0.0075 (10)	−0.0076 (10)
C4	0.0187 (12)	0.0285 (12)	0.0299 (12)	−0.0025 (9)	−0.0001 (9)	−0.0077 (10)
C5	0.0231 (12)	0.0211 (11)	0.0312 (13)	−0.0049 (9)	0.0028 (10)	−0.0024 (9)
C6	0.0335 (14)	0.0237 (12)	0.0248 (12)	−0.0053 (10)	0.0066 (10)	0.0004 (9)
C7	0.0294 (13)	0.0315 (13)	0.0286 (13)	−0.0070 (11)	0.0104 (10)	−0.0078 (10)
C8	0.0160 (12)	0.0302 (13)	0.0419 (14)	0.0009 (10)	0.0005 (10)	−0.0105 (11)
C9	0.0606 (19)	0.0311 (14)	0.0240 (13)	0.0053 (13)	−0.0017 (12)	0.0013 (10)
C17	0.0305 (14)	0.0346 (14)	0.0345 (14)	0.0046 (11)	−0.0039 (11)	−0.0122 (11)
C18	0.0352 (14)	0.0262 (13)	0.0342 (13)	0.0022 (11)	−0.0022 (11)	−0.0046 (10)
S1'	0.0369 (4)	0.0518 (4)	0.0331 (4)	0.0153 (3)	−0.0103 (3)	−0.0025 (3)
C2'	0.0308 (14)	0.0584 (18)	0.0264 (13)	0.0063 (13)	−0.0003 (11)	−0.0119 (12)
C3'	0.0239 (12)	0.0364 (14)	0.0237 (12)	−0.0042 (10)	0.0007 (9)	0.0017 (10)
C4'	0.0214 (12)	0.0253 (12)	0.0280 (12)	−0.0034 (9)	−0.0021 (9)	0.0007 (9)
C5'	0.0233 (12)	0.0221 (12)	0.0300 (12)	−0.0026 (9)	−0.0063 (10)	−0.0003 (9)
C6'	0.0283 (13)	0.0185 (11)	0.0380 (14)	0.0009 (10)	−0.0062 (10)	−0.0067 (10)
C7'	0.0283 (13)	0.0186 (12)	0.0444 (15)	−0.0006 (10)	−0.0104 (11)	0.0032 (10)
C8'	0.0351 (14)	0.0321 (13)	0.0268 (13)	−0.0051 (11)	−0.0064 (11)	0.0090 (10)
C9'	0.0329 (14)	0.0407 (15)	0.0409 (15)	0.0109 (12)	−0.0090 (12)	−0.0196 (12)
C17'	0.0247 (13)	0.0401 (15)	0.0324 (13)	0.0048 (11)	−0.0043 (10)	−0.0059 (11)
C18'	0.0307 (14)	0.0369 (14)	0.0301 (13)	0.0027 (11)	−0.0065 (11)	−0.0070 (11)
S1"	0.0504 (5)	0.0475 (4)	0.0471 (4)	−0.0123 (4)	−0.0004 (3)	0.0177 (3)
C2"	0.0316 (14)	0.0368 (14)	0.0356 (14)	−0.0011 (11)	−0.0114 (11)	−0.0014 (11)
C3"	0.0163 (11)	0.0291 (13)	0.0330 (13)	0.0045 (9)	−0.0053 (9)	−0.0001 (10)
C4"	0.0180 (12)	0.0282 (12)	0.0281 (12)	0.0053 (9)	−0.0016 (9)	0.0026 (10)
C5"	0.0206 (12)	0.0230 (12)	0.0331 (13)	0.0052 (9)	0.0016 (10)	−0.0008 (9)
C6"	0.0263 (13)	0.0263 (12)	0.0284 (12)	0.0088 (10)	0.0007 (10)	−0.0052 (10)
C7"	0.0259 (13)	0.0322 (13)	0.0278 (13)	0.0069 (10)	0.0052 (10)	0.0018 (10)
C8"	0.0171 (12)	0.0281 (13)	0.0393 (14)	0.0031 (10)	0.0011 (10)	0.0038 (10)
C9"	0.0440 (16)	0.0365 (14)	0.0307 (14)	0.0041 (12)	−0.0067 (12)	−0.0073 (11)
C17"	0.0347 (15)	0.0411 (15)	0.0343 (14)	0.0014 (12)	−0.0040 (11)	0.0084 (11)
C18"	0.0302 (14)	0.0256 (13)	0.0446 (15)	0.0015 (11)	−0.0058 (11)	0.0020 (11)
S1*	0.0474 (5)	0.0599 (5)	0.0411 (4)	−0.0192 (4)	0.0166 (3)	−0.0071 (3)
C2*	0.0323 (14)	0.0392 (15)	0.0364 (14)	−0.0045 (11)	−0.0027 (11)	−0.0145 (11)
C3*	0.0273 (13)	0.0217 (12)	0.0351 (13)	0.0017 (10)	−0.0007 (10)	−0.0097 (10)
C4*	0.0272 (13)	0.0218 (12)	0.0268 (12)	0.0043 (10)	0.0017 (10)	−0.0043 (9)
C5*	0.0195 (12)	0.0208 (11)	0.0342 (13)	0.0025 (9)	−0.0009 (10)	−0.0014 (9)
C6*	0.0232 (12)	0.0273 (12)	0.0280 (12)	0.0058 (10)	−0.0056 (10)	0.0005 (9)
C7*	0.0287 (13)	0.0283 (13)	0.0292 (13)	0.0056 (10)	0.0035 (10)	0.0034 (10)
C8*	0.0235 (12)	0.0200 (12)	0.0394 (14)	−0.0005 (9)	0.0037 (10)	−0.0012 (10)
C9*	0.0295 (14)	0.0444 (15)	0.0266 (13)	−0.0027 (11)	−0.0066 (10)	−0.0027 (11)
C17*	0.0369 (15)	0.0396 (15)	0.0302 (13)	−0.0024 (12)	0.0040 (11)	−0.0062 (11)
C18*	0.0241 (13)	0.0311 (13)	0.0387 (14)	−0.0004 (10)	0.0012 (11)	−0.0039 (11)

Geometric parameters (Å, º) top

S1—C18	1.814 (3)	S1"—C18"	1.807 (3)
S1—C17	1.824 (3)	S1"—C17"	1.826 (3)
C2—C3	1.511 (3)	C2"—C3"	1.512 (3)
C2—C9ⁱ	1.589 (4)	C2"—C9"ⁱⁱⁱ	1.590 (4)
C2—H2A	0.9900	C2"—H2"1	0.9900
C2—H2B	0.9900	C2"—H2"2	0.9900
C3—C8	1.387 (3)	C3"—C8"	1.387 (3)
C3—C4	1.402 (3)	C3"—C4"	1.402 (3)
C4—C5	1.386 (3)	C4"—C5"	1.383 (3)
C4—C17	1.507 (3)	C4"—C17"	1.506 (3)
C5—C6	1.402 (3)	C5"—C6"	1.400 (3)
C5—C18	1.504 (3)	C5"—C18"	1.504 (3)
C6—C7	1.390 (3)	C6"—C7"	1.388 (3)
C6—C9	1.508 (4)	C6"—C9"	1.515 (3)
C7—C8	1.384 (4)	C7"—C8"	1.385 (3)
C7—H7	0.9500	C7"—H7"	0.9500
C8—H8	0.9500	C8"—H8"	0.9500
C9—H9A	0.9900	C9"—H9"1	0.9900
C9—H9B	0.9900	C9"—H9"2	0.9900
C17—H17A	0.9900	C17"—H17E	0.9900
C17—H17B	0.9900	C17"—H17F	0.9900
C18—H18A	0.9900	C18"—H18E	0.9900
C18—H18B	0.9900	C18"—H18F	0.9900
S1'—C17'	1.813 (2)	S1—C18	1.811 (3)
S1'—C18'	1.819 (3)	S1—C17	1.818 (3)
C2'—C3'	1.516 (3)	C2—C3	1.514 (3)
C2'—C9'ⁱⁱ	1.585 (4)	C2—C9^iv	1.589 (4)
C2'—H2'1	0.9900	C2—H21	0.9900
C2'—H2'2	0.9900	C2—H22	0.9900
C3'—C8'	1.386 (3)	C3—C8	1.387 (3)
C3'—C4'	1.400 (3)	C3—C4	1.402 (3)
C4'—C5'	1.381 (3)	C4—C5	1.384 (3)
C4'—C17'	1.502 (3)	C4—C17	1.503 (3)
C5'—C6'	1.402 (3)	C5—C6	1.403 (3)
C5'—C18'	1.507 (3)	C5—C18	1.502 (3)
C6'—C7'	1.390 (3)	C6—C7	1.388 (3)
C6'—C9'	1.507 (4)	C6—C9	1.511 (3)
C7'—C8'	1.387 (4)	C7—C8	1.386 (3)
C7'—H7'	0.9500	C7—H7	0.9500
C8'—H8'	0.9500	C8—H8	0.9500
C9'—H9'1	0.9900	C9—H91	0.9900
C9'—H9'2	0.9900	C9—H92	0.9900
C17'—H17C	0.9900	C17*—H17G	0.9900
C17'—H17D	0.9900	C17*—H17H	0.9900
C18'—H18C	0.9900	C18*—H18G	0.9900
C18'—H18D	0.9900	C18*—H18H	0.9900

C18—S1—C17	95.62 (11)	C18"—S1"—C17"	95.74 (12)
C3—C2—C9ⁱ	112.5 (2)	C3"—C2"—C9"ⁱⁱⁱ	112.9 (2)
C3—C2—H2A	109.1	C3"—C2"—H2"1	109.0
C9ⁱ—C2—H2A	109.1	C9"ⁱⁱⁱ—C2"—H2"1	109.0
C3—C2—H2B	109.1	C3"—C2"—H2"2	109.0
C9ⁱ—C2—H2B	109.1	C9"ⁱⁱⁱ—C2"—H2"2	109.0
H2A—C2—H2B	107.8	H2"1—C2"—H2"2	107.8
C8—C3—C4	116.5 (2)	C8"—C3"—C4"	116.6 (2)
C8—C3—C2	120.8 (2)	C8"—C3"—C2"	120.8 (2)
C4—C3—C2	121.5 (2)	C4"—C3"—C2"	121.5 (2)
C5—C4—C3	120.7 (2)	C5"—C4"—C3"	120.6 (2)
C5—C4—C17	115.6 (2)	C5"—C4"—C17"	115.6 (2)
C3—C4—C17	123.3 (2)	C3"—C4"—C17"	123.5 (2)
C4—C5—C6	120.8 (2)	C4"—C5"—C6"	120.9 (2)
C4—C5—C18	115.9 (2)	C4"—C5"—C18"	116.1 (2)
C6—C5—C18	122.9 (2)	C6"—C5"—C18"	122.7 (2)
C7—C6—C5	116.5 (2)	C7"—C6"—C5"	116.6 (2)
C7—C6—C9	121.2 (2)	C7"—C6"—C9"	121.2 (2)
C5—C6—C9	121.0 (2)	C5"—C6"—C9"	120.9 (2)
C8—C7—C6	121.1 (2)	C8"—C7"—C6"	120.9 (2)
C8—C7—H7	119.5	C8"—C7"—H7"	119.5
C6—C7—H7	119.5	C6"—C7"—H7"	119.5
C7—C8—C3	121.2 (2)	C7"—C8"—C3"	121.1 (2)
C7—C8—H8	119.4	C7"—C8"—H8"	119.5
C3—C8—H8	119.4	C3"—C8"—H8"	119.5
C6—C9—C2ⁱ	112.6 (2)	C6"—C9"—C2"ⁱⁱⁱ	112.0 (2)
C6—C9—H9A	109.1	C6"—C9"—H9"1	109.2
C2ⁱ—C9—H9A	109.1	C2"ⁱⁱⁱ—C9"—H9"1	109.2
C6—C9—H9B	109.1	C6"—C9"—H9"2	109.2
C2ⁱ—C9—H9B	109.1	C2"ⁱⁱⁱ—C9"—H9"2	109.2
H9A—C9—H9B	107.8	H9"1—C9"—H9"2	107.9
C4—C17—S1	106.26 (17)	C4"—C17"—S1"	106.08 (18)
C4—C17—H17A	110.5	C4"—C17"—H17E	110.5
S1—C17—H17A	110.5	S1"—C17"—H17E	110.5
C4—C17—H17B	110.5	C4"—C17"—H17F	110.5
S1—C17—H17B	110.5	S1"—C17"—H17F	110.5
H17A—C17—H17B	108.7	H17E—C17"—H17F	108.7
C5—C18—S1	106.57 (17)	C5"—C18"—S1"	106.48 (17)
C5—C18—H18A	110.4	C5"—C18"—H18E	110.4
S1—C18—H18A	110.4	S1"—C18"—H18E	110.4
C5—C18—H18B	110.4	C5"—C18"—H18F	110.4
S1—C18—H18B	110.4	S1"—C18"—H18F	110.4
H18A—C18—H18B	108.6	H18E—C18"—H18F	108.6
C17'—S1'—C18'	95.44 (11)	C18—S1—C17*	95.87 (12)
C3'—C2'—C9'ⁱⁱ	111.9 (2)	C3—C2—C9*^iv	111.92 (19)
C3'—C2'—H2'1	109.2	C3—C2—H2*1	109.2
C9'ⁱⁱ—C2'—H2'1	109.2	C9^iv—C2—H2*1	109.2
C3'—C2'—H2'2	109.2	C3—C2—H2*2	109.2
C9'ⁱⁱ—C2'—H2'2	109.2	C9^iv—C2—H2*2	109.2
H2'1—C2'—H2'2	107.9	H21—C2—H2*2	107.9
C8'—C3'—C4'	116.6 (2)	C8—C3—C4*	116.7 (2)
C8'—C3'—C2'	121.3 (2)	C8—C3—C2*	120.5 (2)
C4'—C3'—C2'	120.7 (2)	C4—C3—C2*	121.6 (2)
C5'—C4'—C3'	120.8 (2)	C5—C4—C3*	120.4 (2)
C5'—C4'—C17'	115.7 (2)	C5—C4—C17*	115.7 (2)
C3'—C4'—C17'	123.1 (2)	C3—C4—C17*	123.5 (2)
C4'—C5'—C6'	120.8 (2)	C4—C5—C6*	121.0 (2)
C4'—C5'—C18'	115.7 (2)	C4—C5—C18*	116.0 (2)
C6'—C5'—C18'	123.1 (2)	C6—C5—C18*	122.6 (2)
C7'—C6'—C5'	116.5 (2)	C7—C6—C5*	116.4 (2)
C7'—C6'—C9'	121.4 (2)	C7—C6—C9*	121.1 (2)
C5'—C6'—C9'	121.0 (2)	C5—C6—C9*	121.4 (2)
C8'—C7'—C6'	121.0 (2)	C8—C7—C6*	120.9 (2)
C8'—C7'—H7'	119.5	C8—C7—H7*	119.5
C6'—C7'—H7'	119.5	C6—C7—H7*	119.5
C3'—C8'—C7'	121.0 (2)	C7—C8—C3*	121.1 (2)
C3'—C8'—H8'	119.5	C7—C8—H8*	119.4
C7'—C8'—H8'	119.5	C3—C8—H8*	119.4
C6'—C9'—C2'ⁱⁱ	113.3 (2)	C6—C9—C2*^iv	113.00 (19)
C6'—C9'—H9'1	108.9	C6—C9—H9*1	109.0
C2'ⁱⁱ—C9'—H9'1	108.9	C2^iv—C9—H9*1	109.0
C6'—C9'—H9'2	108.9	C6—C9—H9*2	109.0
C2'ⁱⁱ—C9'—H9'2	108.9	C2^iv—C9—H9*2	109.0
H9'1—C9'—H9'2	107.7	H91—C9—H9*2	107.8
C4'—C17'—S1'	106.72 (17)	C4—C17—S1*	106.13 (17)
C4'—C17'—H17C	110.4	C4—C17—H17G	110.5
S1'—C17'—H17C	110.4	S1—C17—H17G	110.5
C4'—C17'—H17D	110.4	C4—C17—H17H	110.5
S1'—C17'—H17D	110.4	S1—C17—H17H	110.5
H17C—C17'—H17D	108.6	H17G—C17*—H17H	108.7
C5'—C18'—S1'	106.36 (17)	C5—C18—S1*	106.25 (17)
C5'—C18'—H18C	110.5	C5—C18—H18G	110.5
S1'—C18'—H18C	110.5	S1—C18—H18G	110.5
C5'—C18'—H18D	110.5	C5—C18—H18H	110.5
S1'—C18'—H18D	110.5	S1—C18—H18H	110.5
H18C—C18'—H18D	108.6	H18G—C18*—H18H	108.7

C9ⁱ—C2—C3—C8	−95.1 (3)	C9"ⁱⁱⁱ—C2"—C3"—C8"	95.6 (3)
C9ⁱ—C2—C3—C4	72.1 (3)	C9"ⁱⁱⁱ—C2"—C3"—C4"	−72.2 (3)
C8—C3—C4—C5	14.8 (3)	C8"—C3"—C4"—C5"	−15.2 (3)
C2—C3—C4—C5	−152.9 (2)	C2"—C3"—C4"—C5"	153.1 (2)
C8—C3—C4—C17	−171.4 (2)	C8"—C3"—C4"—C17"	171.6 (2)
C2—C3—C4—C17	20.8 (3)	C2"—C3"—C4"—C17"	−20.1 (3)
C3—C4—C5—C6	−0.7 (3)	C3"—C4"—C5"—C6"	1.0 (3)
C17—C4—C5—C6	−174.9 (2)	C17"—C4"—C5"—C6"	174.7 (2)
C3—C4—C5—C18	172.1 (2)	C3"—C4"—C5"—C18"	−172.2 (2)
C17—C4—C5—C18	−2.1 (3)	C17"—C4"—C5"—C18"	1.5 (3)
C4—C5—C6—C7	−13.9 (3)	C4"—C5"—C6"—C7"	14.0 (3)
C18—C5—C6—C7	173.8 (2)	C18"—C5"—C6"—C7"	−173.2 (2)
C4—C5—C6—C9	153.3 (2)	C4"—C5"—C6"—C9"	−153.3 (2)
C18—C5—C6—C9	−19.0 (3)	C18"—C5"—C6"—C9"	19.5 (3)
C5—C6—C7—C8	14.5 (3)	C5"—C6"—C7"—C8"	−14.9 (3)
C9—C6—C7—C8	−152.7 (2)	C9"—C6"—C7"—C8"	152.3 (2)
C6—C7—C8—C3	−0.3 (4)	C6"—C7"—C8"—C3"	0.7 (3)
C4—C3—C8—C7	−14.4 (3)	C4"—C3"—C8"—C7"	14.4 (3)
C2—C3—C8—C7	153.5 (2)	C2"—C3"—C8"—C7"	−154.0 (2)
C7—C6—C9—C2ⁱ	94.8 (3)	C7"—C6"—C9"—C2"ⁱⁱⁱ	−95.2 (3)
C5—C6—C9—C2ⁱ	−71.7 (3)	C5"—C6"—C9"—C2"ⁱⁱⁱ	71.5 (3)
C5—C4—C17—S1	2.0 (3)	C5"—C4"—C17"—S1"	−0.3 (3)
C3—C4—C17—S1	−172.02 (19)	C3"—C4"—C17"—S1"	173.21 (18)
C18—S1—C17—C4	−1.12 (19)	C18"—S1"—C17"—C4"	−0.73 (19)
C4—C5—C18—S1	1.1 (3)	C4"—C5"—C18"—S1"	−1.9 (3)
C6—C5—C18—S1	173.75 (19)	C6"—C5"—C18"—S1"	−175.04 (18)
C17—S1—C18—C5	0.11 (19)	C17"—S1"—C18"—C5"	1.44 (19)
C9'ⁱⁱ—C2'—C3'—C8'	94.3 (3)	C9^iv—C2—C3—C8	−94.0 (3)
C9'ⁱⁱ—C2'—C3'—C4'	−71.5 (3)	C9^iv—C2—C3—C4	72.9 (3)
C8'—C3'—C4'—C5'	−14.4 (3)	C8—C3—C4—C5	15.2 (3)
C2'—C3'—C4'—C5'	152.0 (2)	C2—C3—C4—C5	−152.1 (2)
C8'—C3'—C4'—C17'	172.8 (2)	C8—C3—C4—C17	−171.3 (2)
C2'—C3'—C4'—C17'	−20.8 (4)	C2—C3—C4—C17	21.4 (3)
C3'—C4'—C5'—C6'	0.0 (3)	C3—C4—C5—C6	−0.7 (3)
C17'—C4'—C5'—C6'	173.2 (2)	C17—C4—C5—C6	−174.8 (2)
C3'—C4'—C5'—C18'	−173.7 (2)	C3—C4—C5—C18	171.5 (2)
C17'—C4'—C5'—C18'	−0.4 (3)	C17—C4—C5—C18	−2.5 (3)
C4'—C5'—C6'—C7'	14.1 (3)	C4—C5—C6—C7	−14.3 (3)
C18'—C5'—C6'—C7'	−172.7 (2)	C18—C5—C6—C7	174.0 (2)
C4'—C5'—C6'—C9'	−154.4 (2)	C4—C5—C6—C9	154.3 (2)
C18'—C5'—C6'—C9'	18.8 (4)	C18—C5—C6—C9	−17.5 (3)
C5'—C6'—C7'—C8'	−13.8 (3)	C5—C6—C7—C8	14.9 (3)
C9'—C6'—C7'—C8'	154.6 (2)	C9—C6—C7—C8	−153.7 (2)
C4'—C3'—C8'—C7'	14.8 (3)	C6—C7—C8—C3	−0.4 (4)
C2'—C3'—C8'—C7'	−151.6 (2)	C4—C3—C8—C7	−14.7 (3)
C6'—C7'—C8'—C3'	−0.6 (4)	C2—C3—C8—C7	152.8 (2)
C7'—C6'—C9'—C2'ⁱⁱ	−95.4 (3)	C7—C6—C9—C2^iv	94.8 (3)
C5'—C6'—C9'—C2'ⁱⁱ	72.5 (3)	C5—C6—C9—C2^iv	−73.2 (3)
C5'—C4'—C17'—S1'	−0.3 (3)	C5—C4—C17—S1	1.4 (3)
C3'—C4'—C17'—S1'	172.78 (19)	C3—C4—C17—S1	−172.38 (19)
C18'—S1'—C17'—C4'	0.76 (19)	C18—S1—C17—C4	−0.04 (19)
C4'—C5'—C18'—S1'	1.0 (3)	C4—C5—C18—S1	2.3 (3)
C6'—C5'—C18'—S1'	−172.55 (19)	C6—C5—C18—S1	174.38 (18)
C17'—S1'—C18'—C5'	−0.97 (19)	C17—S1—C18—C5	−1.17 (18)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2"—H2"2···S1′	0.99	2.95	3.723 (3)	136
C9"—H9"2···S1′ⁱⁱⁱ	0.99	3.02	3.732 (3)	130
C9—H91···S1"^v	0.99	2.96	3.937 (3)	168
C7—H7···S1*^vi	0.95	2.94	3.854 (3)	162
C9′—H9′1···S1	0.99	3.07	3.907 (3)	143
C8"—H8"···S1^vii	0.95	3.08	3.896 (3)	145
C8—H8···S1′^v	0.95	3.10	3.879 (3)	140
C17—H17B···S1*^viii	0.99	3.07	3.974 (3)	153
C18"—H18F···Cg1^ix	1.08	2.74	3.63	140
C18—H18A···Cg3	1.08	2.78	3.66	111
C17′—H17C···Cg4ⁱⁱ	1.08	2.61	3.45	135
C2—H22···Cg2^v	1.08	2.98	4.04	166

Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z; (v) x+1, y, z; (vi) x, y, z−1; (vii) −x+1, −y+1, −z; (viii) −x+1, −y, −z+1; (ix) x−1, y, z.

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[2.2]Dihydro­isobenzothio­phenophane

Supporting information

Key indicators

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[2.2]Dihydroisobenzothiophenophane