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The title compound, C16H12, crystallizes with four half mol­ecules in the asymmetric unit, each of which is located on a crystallographic centre of inversion. The mol­ecules are essentially planar. The crystal studied was a non-merohedral twin.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314619011799/bt4085sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314619011799/bt4085Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314619011799/bt4085Isup3.cml
Supplementary material

CCDC reference: 1949606

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.056
  • wR factor = 0.141
  • Data-to-parameter ratio = 49.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C2D --C3D . 11.0 s.u.
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00427 Ang. PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 2.323 Check PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 9 Report
Alert level G PLAT870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed .. ! Info PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 2 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 87 Note PLAT931_ALERT_5_G CIFcalcFCF Twin Law ( 0 0 1) Est.d BASF 0.49 Check PLAT931_ALERT_5_G CIFcalcFCF Twin Law ( 1 1-1) Est.d BASF 0.29 Check
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 3 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 0 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 4 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 1996); cell refinement: X-AREA (Stoe & Cie, 1996); data reduction: X-RED (Stoe & Cie, 1996); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b).

5,10-Dihydroindeno[2,1-a]indene top
Crystal data top
C16H12Z = 4
Mr = 204.26F(000) = 432
Triclinic, P1Dx = 1.255 Mg m3
a = 7.5009 (9) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.6819 (9) ÅCell parameters from 2411 reflections
c = 19.387 (3) Åθ = 2.8–28.0°
α = 99.733 (11)°µ = 0.07 mm1
β = 100.641 (11)°T = 193 K
γ = 90.523 (9)°Plate, colourless
V = 1081.2 (2) Å30.22 × 0.15 × 0.04 mm
Data collection top
Stoe IPDS 2T
diffractometer
7500 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focusθmax = 28.4°, θmin = 2.7°
Detector resolution: 6.67 pixels mm-1h = 99
rotation method scansk = 1010
14443 measured reflectionsl = 2525
14443 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.141 w = 1/[σ2(Fo2) + (0.0513P)2 + 0.1143P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
14443 reflectionsΔρmax = 0.29 e Å3
290 parametersΔρmin = 0.21 e Å3
0 restraints
Special details top

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.

Refinement. Refined as a 2-component twin. BASF 0.40850 Twin law for transforming hkl(1) to hkl(2): -1.00006 0.00023 0.00003 0.00016 -1.00020 0.00001 0.95946 0.87001 1.00038

Hydrogen atoms attached to carbons were placed at calculated positions and were refined in the riding-model approximation with isotropic displacement parameters set to 1.2 Ueq(C).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C1A0.6265 (4)0.1349 (3)0.58366 (16)0.0420 (7)
H1A0.5702700.2391990.6071000.050*
H1B0.7583940.1602780.5889480.050*
C2A0.5377 (3)0.0821 (3)0.50682 (15)0.0379 (7)
C3A0.5094 (3)0.1575 (3)0.44194 (16)0.0371 (7)
C4A0.5622 (3)0.3197 (3)0.42737 (17)0.0424 (7)
H4A0.6277030.4069850.4641470.051*
C5A0.5171 (4)0.3509 (4)0.35798 (18)0.0463 (8)
H5A0.5533280.4603410.3470820.056*
C6A0.4206 (4)0.2254 (4)0.30472 (18)0.0475 (8)
H6A0.3905930.2500000.2576420.057*
C7A0.3663 (4)0.0633 (4)0.31857 (17)0.0461 (8)
H7A0.2996030.0225370.2815310.055*
C8A0.4111 (3)0.0299 (3)0.38696 (16)0.0396 (7)
C1B0.9607 (4)0.6291 (3)0.58564 (17)0.0485 (8)
H1C0.8349720.6521700.5925010.058*
H1D1.0408490.7336460.6091370.058*
C2B0.9702 (4)0.5806 (3)0.50825 (17)0.0428 (7)
C3B0.9306 (3)0.6610 (3)0.44363 (17)0.0416 (7)
C4B0.8648 (4)0.8222 (3)0.43136 (18)0.0472 (8)
H4B0.8377650.9070550.4693070.057*
C5B0.8391 (4)0.8579 (4)0.36300 (19)0.0512 (8)
H5B0.7922980.9679560.3539380.061*
C6B0.8799 (4)0.7372 (4)0.30744 (19)0.0523 (8)
H6B0.8621140.7656770.2609010.063*
C7B0.9472 (4)0.5735 (4)0.3191 (2)0.0537 (9)
H7B0.9749210.4898980.2808730.064*
C8B0.9724 (3)0.5359 (3)0.38743 (18)0.0439 (7)
C1C0.6484 (4)0.4528 (4)0.08155 (17)0.0491 (8)
H1E0.7601770.5270690.1024050.059*
H1F0.6709750.3287680.0872300.059*
C2C0.5827 (3)0.4677 (3)0.00581 (17)0.0422 (7)
C3C0.6498 (4)0.4309 (3)0.06130 (17)0.0422 (7)
C4C0.8104 (4)0.3624 (3)0.07899 (18)0.0506 (8)
H4C0.9032170.3301260.0435410.061*
C5C0.8316 (4)0.3425 (3)0.14959 (19)0.0530 (8)
H5C0.9395570.2953840.1627280.064*
C6C0.6969 (4)0.3906 (4)0.20061 (19)0.0537 (8)
H6C0.7136960.3771950.2485810.064*
C7C0.5370 (4)0.4585 (4)0.18306 (19)0.0512 (8)
H7C0.4450290.4911650.2187060.061*
C8C0.5134 (4)0.4776 (3)0.11433 (17)0.0429 (7)
C1D0.1447 (4)0.1273 (4)0.08064 (18)0.0545 (8)
H1G0.1685420.2557300.0838980.065*
H1H0.2551700.0744070.1035470.065*
C2D0.0818 (4)0.0383 (3)0.00570 (18)0.0461 (8)
C3D0.1529 (4)0.0084 (3)0.06117 (18)0.0451 (7)
C4D0.3153 (4)0.0594 (3)0.07869 (19)0.0525 (8)
H4D0.4063670.1278110.0438340.063*
C5D0.3409 (4)0.0080 (4)0.1484 (2)0.0555 (8)
H5D0.4503380.0419990.1615360.067*
C6D0.2082 (5)0.0922 (4)0.1985 (2)0.0569 (9)
H6D0.2279750.1284830.2457490.068*
C7D0.0464 (4)0.1404 (4)0.18077 (19)0.0538 (8)
H7D0.0449610.2080780.2157380.065*
C8D0.0193 (4)0.0903 (3)0.11304 (19)0.0467 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0377 (15)0.0378 (14)0.0459 (19)0.0018 (11)0.0034 (13)0.0003 (12)
C2A0.0280 (14)0.0375 (14)0.046 (2)0.0033 (11)0.0065 (13)0.0017 (13)
C3A0.0260 (13)0.0400 (14)0.045 (2)0.0029 (10)0.0086 (13)0.0063 (13)
C4A0.0326 (14)0.0404 (15)0.052 (2)0.0012 (11)0.0064 (14)0.0024 (14)
C5A0.0391 (16)0.0437 (16)0.059 (2)0.0007 (12)0.0120 (15)0.0131 (15)
C6A0.0438 (17)0.0529 (17)0.046 (2)0.0044 (13)0.0081 (15)0.0107 (15)
C7A0.0433 (17)0.0443 (16)0.047 (2)0.0017 (12)0.0047 (15)0.0003 (14)
C8A0.0309 (14)0.0378 (14)0.050 (2)0.0030 (11)0.0107 (14)0.0028 (13)
C1B0.0444 (17)0.0417 (15)0.058 (2)0.0015 (12)0.0159 (15)0.0037 (13)
C2B0.0300 (13)0.0409 (14)0.055 (2)0.0026 (10)0.0113 (13)0.0038 (14)
C3B0.0285 (14)0.0421 (15)0.054 (2)0.0032 (11)0.0119 (14)0.0043 (14)
C4B0.0367 (15)0.0449 (16)0.060 (2)0.0036 (12)0.0139 (15)0.0048 (15)
C5B0.0392 (16)0.0478 (17)0.068 (3)0.0023 (12)0.0127 (16)0.0111 (16)
C6B0.0483 (18)0.0549 (18)0.055 (2)0.0045 (14)0.0114 (16)0.0123 (16)
C7B0.0486 (18)0.0484 (18)0.062 (3)0.0057 (14)0.0153 (17)0.0023 (16)
C8B0.0325 (14)0.0396 (15)0.058 (2)0.0045 (11)0.0101 (14)0.0017 (14)
C1C0.0473 (17)0.0473 (16)0.051 (2)0.0010 (13)0.0026 (15)0.0165 (14)
C2C0.0426 (15)0.0292 (13)0.051 (2)0.0031 (11)0.0029 (15)0.0103 (13)
C3C0.0506 (17)0.0307 (14)0.046 (2)0.0035 (12)0.0108 (15)0.0083 (13)
C4C0.0574 (19)0.0395 (15)0.055 (2)0.0042 (13)0.0067 (17)0.0138 (15)
C5C0.057 (2)0.0428 (16)0.060 (2)0.0033 (13)0.0187 (18)0.0043 (15)
C6C0.066 (2)0.0473 (17)0.048 (2)0.0080 (15)0.0156 (18)0.0038 (15)
C7C0.0547 (19)0.0494 (17)0.047 (2)0.0093 (14)0.0039 (16)0.0083 (15)
C8C0.0464 (17)0.0334 (14)0.047 (2)0.0053 (12)0.0060 (15)0.0067 (13)
C1D0.0495 (18)0.0459 (16)0.062 (2)0.0013 (13)0.0032 (16)0.0057 (15)
C2D0.0440 (16)0.0286 (14)0.059 (2)0.0023 (11)0.0074 (16)0.0065 (14)
C3D0.0525 (18)0.0321 (14)0.053 (2)0.0110 (12)0.0115 (16)0.0130 (13)
C4D0.0554 (19)0.0352 (15)0.063 (3)0.0011 (13)0.0002 (17)0.0086 (15)
C5D0.055 (2)0.0489 (17)0.069 (3)0.0053 (14)0.0181 (18)0.0218 (17)
C6D0.068 (2)0.0544 (18)0.051 (2)0.0175 (16)0.0114 (19)0.0142 (16)
C7D0.0508 (19)0.0484 (17)0.058 (2)0.0094 (14)0.0006 (17)0.0090 (16)
C8D0.0456 (17)0.0354 (15)0.058 (2)0.0071 (12)0.0029 (16)0.0117 (14)
Geometric parameters (Å, º) top
C1A—C2A1.500 (4)C1C—C2C1.484 (4)
C1A—C8Ai1.518 (4)C1C—C8Ciii1.531 (4)
C1A—H1A0.9900C1C—H1E0.9900
C1A—H1B0.9900C1C—H1F0.9900
C2A—C2Ai1.341 (4)C2C—C2Ciii1.335 (5)
C2A—C3A1.453 (4)C2C—C3C1.465 (4)
C3A—C4A1.393 (3)C3C—C4C1.396 (4)
C3A—C8A1.408 (4)C3C—C8C1.406 (4)
C4A—C5A1.387 (4)C4C—C5C1.390 (4)
C4A—H4A0.9500C4C—H4C0.9500
C5A—C6A1.376 (4)C5C—C6C1.377 (4)
C5A—H5A0.9500C5C—H5C0.9500
C6A—C7A1.390 (4)C6C—C7C1.388 (4)
C6A—H6A0.9500C6C—H6C0.9500
C7A—C8A1.374 (4)C7C—C8C1.360 (4)
C7A—H7A0.9500C7C—H7C0.9500
C1B—C2B1.499 (4)C1D—C2D1.485 (4)
C1B—C8Bii1.506 (4)C1D—C8Div1.526 (4)
C1B—H1C0.9900C1D—H1G0.9900
C1B—H1D0.9900C1D—H1H0.9900
C2B—C2Bii1.329 (5)C2D—C2Div1.321 (5)
C2B—C3B1.472 (4)C2D—C3D1.475 (4)
C3B—C4B1.379 (4)C3D—C4D1.393 (4)
C3B—C8B1.410 (4)C3D—C8D1.395 (4)
C4B—C5B1.378 (4)C4D—C5D1.392 (4)
C4B—H4B0.9500C4D—H4D0.9500
C5B—C6B1.379 (4)C5D—C6D1.380 (4)
C5B—H5B0.9500C5D—H5D0.9500
C6B—C7B1.397 (4)C6D—C7D1.385 (4)
C6B—H6B0.9500C6D—H6D0.9500
C7B—C8B1.384 (4)C7D—C8D1.357 (4)
C7B—H7B0.9500C7D—H7D0.9500
C2A—C1A—C8Ai101.2 (2)C2C—C1C—C8Ciii100.7 (2)
C2A—C1A—H1A111.5C2C—C1C—H1E111.6
C8Ai—C1A—H1A111.5C8Ciii—C1C—H1E111.6
C2A—C1A—H1B111.5C2C—C1C—H1F111.6
C8Ai—C1A—H1B111.5C8Ciii—C1C—H1F111.6
H1A—C1A—H1B109.3H1E—C1C—H1F109.4
C2Ai—C2A—C3A109.8 (3)C2Ciii—C2C—C3C109.6 (3)
C2Ai—C2A—C1A111.8 (3)C2Ciii—C2C—C1C113.0 (4)
C3A—C2A—C1A138.4 (2)C3C—C2C—C1C137.4 (2)
C4A—C3A—C8A120.1 (3)C4C—C3C—C8C120.1 (3)
C4A—C3A—C2A132.5 (3)C4C—C3C—C2C133.1 (3)
C8A—C3A—C2A107.5 (2)C8C—C3C—C2C106.8 (2)
C5A—C4A—C3A118.5 (3)C5C—C4C—C3C118.6 (3)
C5A—C4A—H4A120.7C5C—C4C—H4C120.7
C3A—C4A—H4A120.7C3C—C4C—H4C120.7
C6A—C5A—C4A120.9 (3)C6C—C5C—C4C120.4 (3)
C6A—C5A—H5A119.6C6C—C5C—H5C119.8
C4A—C5A—H5A119.6C4C—C5C—H5C119.8
C5A—C6A—C7A121.2 (3)C5C—C6C—C7C121.1 (3)
C5A—C6A—H6A119.4C5C—C6C—H6C119.5
C7A—C6A—H6A119.4C7C—C6C—H6C119.5
C8A—C7A—C6A118.6 (3)C8C—C7C—C6C119.3 (3)
C8A—C7A—H7A120.7C8C—C7C—H7C120.3
C6A—C7A—H7A120.7C6C—C7C—H7C120.3
C7A—C8A—C3A120.7 (3)C7C—C8C—C3C120.5 (3)
C7A—C8A—C1Ai129.7 (3)C7C—C8C—C1Ciii129.5 (3)
C3A—C8A—C1Ai109.6 (3)C3C—C8C—C1Ciii109.9 (3)
C2B—C1B—C8Bii101.0 (2)C2D—C1D—C8Div100.7 (2)
C2B—C1B—H1C111.6C2D—C1D—H1G111.6
C8Bii—C1B—H1C111.6C8Div—C1D—H1G111.6
C2B—C1B—H1D111.6C2D—C1D—H1H111.6
C8Bii—C1B—H1D111.6C8Div—C1D—H1H111.6
H1C—C1B—H1D109.4H1G—C1D—H1H109.4
C2Bii—C2B—C3B109.3 (4)C2Div—C2D—C3D109.2 (4)
C2Bii—C2B—C1B112.7 (4)C2Div—C2D—C1D113.2 (4)
C3B—C2B—C1B138.0 (2)C3D—C2D—C1D137.5 (2)
C4B—C3B—C8B120.6 (3)C4D—C3D—C8D120.2 (3)
C4B—C3B—C2B132.7 (3)C4D—C3D—C2D132.9 (3)
C8B—C3B—C2B106.7 (2)C8D—C3D—C2D106.9 (3)
C5B—C4B—C3B118.7 (3)C5D—C4D—C3D118.5 (3)
C5B—C4B—H4B120.7C5D—C4D—H4D120.8
C3B—C4B—H4B120.7C3D—C4D—H4D120.8
C4B—C5B—C6B121.5 (3)C6D—C5D—C4D120.3 (3)
C4B—C5B—H5B119.3C6D—C5D—H5D119.8
C6B—C5B—H5B119.3C4D—C5D—H5D119.8
C5B—C6B—C7B120.5 (3)C5D—C6D—C7D120.7 (3)
C5B—C6B—H6B119.7C5D—C6D—H6D119.6
C7B—C6B—H6B119.7C7D—C6D—H6D119.6
C8B—C7B—C6B118.5 (3)C8D—C7D—C6D119.6 (3)
C8B—C7B—H7B120.7C8D—C7D—H7D120.2
C6B—C7B—H7B120.7C6D—C7D—H7D120.2
C7B—C8B—C3B120.2 (3)C7D—C8D—C3D120.7 (3)
C7B—C8B—C1Bii129.5 (3)C7D—C8D—C1Div129.4 (3)
C3B—C8B—C1Bii110.3 (3)C3D—C8D—C1Div109.9 (3)
C8Ai—C1A—C2A—C2Ai0.1 (3)C8Ciii—C1C—C2C—C2Ciii0.0 (4)
C8Ai—C1A—C2A—C3A179.9 (3)C8Ciii—C1C—C2C—C3C180.0 (3)
C2Ai—C2A—C3A—C4A178.8 (3)C2Ciii—C2C—C3C—C4C179.4 (3)
C1A—C2A—C3A—C4A1.0 (5)C1C—C2C—C3C—C4C0.6 (5)
C2Ai—C2A—C3A—C8A0.1 (3)C2Ciii—C2C—C3C—C8C0.0 (3)
C1A—C2A—C3A—C8A179.9 (3)C1C—C2C—C3C—C8C180.0 (3)
C8A—C3A—C4A—C5A0.5 (4)C8C—C3C—C4C—C5C0.2 (4)
C2A—C3A—C4A—C5A178.3 (3)C2C—C3C—C4C—C5C179.5 (3)
C3A—C4A—C5A—C6A0.7 (4)C3C—C4C—C5C—C6C0.4 (4)
C4A—C5A—C6A—C7A0.4 (4)C4C—C5C—C6C—C7C0.5 (4)
C5A—C6A—C7A—C8A0.1 (4)C5C—C6C—C7C—C8C0.0 (4)
C6A—C7A—C8A—C3A0.3 (4)C6C—C7C—C8C—C3C0.6 (4)
C6A—C7A—C8A—C1Ai178.5 (2)C6C—C7C—C8C—C1Ciii179.6 (2)
C4A—C3A—C8A—C7A0.0 (4)C4C—C3C—C8C—C7C0.7 (4)
C2A—C3A—C8A—C7A179.1 (2)C2C—C3C—C8C—C7C179.8 (2)
C4A—C3A—C8A—C1Ai179.0 (2)C4C—C3C—C8C—C1Ciii179.5 (2)
C2A—C3A—C8A—C1Ai0.1 (3)C2C—C3C—C8C—C1Ciii0.0 (3)
C8Bii—C1B—C2B—C2Bii0.2 (4)C8Div—C1D—C2D—C2Div0.7 (4)
C8Bii—C1B—C2B—C3B179.7 (3)C8Div—C1D—C2D—C3D179.7 (3)
C2Bii—C2B—C3B—C4B179.1 (3)C2Div—C2D—C3D—C4D179.8 (3)
C1B—C2B—C3B—C4B0.4 (5)C1D—C2D—C3D—C4D1.2 (5)
C2Bii—C2B—C3B—C8B0.4 (4)C2Div—C2D—C3D—C8D0.4 (4)
C1B—C2B—C3B—C8B179.9 (3)C1D—C2D—C3D—C8D179.4 (3)
C8B—C3B—C4B—C5B0.6 (4)C8D—C3D—C4D—C5D0.8 (4)
C2B—C3B—C4B—C5B178.9 (3)C2D—C3D—C4D—C5D179.9 (3)
C3B—C4B—C5B—C6B0.9 (4)C3D—C4D—C5D—C6D0.4 (4)
C4B—C5B—C6B—C7B0.7 (4)C4D—C5D—C6D—C7D1.2 (4)
C5B—C6B—C7B—C8B0.3 (4)C5D—C6D—C7D—C8D0.8 (4)
C6B—C7B—C8B—C3B0.0 (4)C6D—C7D—C8D—C3D0.3 (4)
C6B—C7B—C8B—C1Bii178.9 (3)C6D—C7D—C8D—C1Div179.6 (3)
C4B—C3B—C8B—C7B0.2 (4)C4D—C3D—C8D—C7D1.1 (4)
C2B—C3B—C8B—C7B179.4 (2)C2D—C3D—C8D—C7D179.4 (2)
C4B—C3B—C8B—C1Bii179.3 (2)C4D—C3D—C8D—C1Div179.5 (2)
C2B—C3B—C8B—C1Bii0.3 (3)C2D—C3D—C8D—C1Div0.0 (3)
Symmetry codes: (i) x+1, y, z+1; (ii) x+2, y+1, z+1; (iii) x+1, y+1, z; (iv) x, y, z.
 

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