Download citation
Download citation
link to html
6,13-Di­hydro­pentacene and pentacene cocrystallize in a ratio of 2:1, i.e. C22H16·0.5C22H14, during vapour transport of commercial pentacene in a gas flow. The crystal structure is monoclinic, space group P21/n, and contains one di­hydro­pentacene mol­ecule and half a pentacene mol­ecule in the asymmetric unit.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802018445/su6002sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802018445/su6002Isup2.hkl
Contains datablock I

CCDC reference: 200763

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.013 Å
  • R factor = 0.064
  • wR factor = 0.151
  • Data-to-parameter ratio = 6.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Red Alert Alert Level A:
THETM_01 Alert A The value of sine(theta_max)/wavelength is less than 0.550 Calculated sin(theta_max)/wavelength = 0.4812
Amber Alert Alert Level B:
REFNR_01 Alert B Ratio of reflections to parameters is < 8 for a centrosymmetric structure sine(theta)/lambda 0.4812 Proportion of unique data used 1.0000 Ratio reflections to parameters 6.6923
Yellow Alert Alert Level C:
RINTA_01 Alert C The value of Rint is greater than 0.10 Rint given 0.123
1 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: CAD4-UNIX Software (Enraf-Nonius, 1994); cell refinement: SET4 (de Boer & Duisenberg, 1984); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTO (Meetsma, 2002) and PLATON (Spek, 1994); software used to prepare material for publication: PLATON (Spek, 1990).

6,13-dihydropentacene? top
Crystal data top
C22H16·0.5C22H14F(000) = 884
Mr = 419.51Unit cell parameters (Duisenberg, 1992) and orientation matrix were determined from a least-squares treatment of SET4 (de Boer & Duisenberg, 1984)setting. Reduced cell calculations did not indicate any higher metric lattice symmetry and examination of the final atomic coordinates of the structure did not yield extra symmetry elements (Spek, 1988; Le Page 1987, 1988)
Monoclinic, P21/nDx = 1.293 Mg m3
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 6.163 (4) ÅCell parameters from 23 reflections
b = 21.801 (5) Åθ = 6.3–11.5°
c = 16.069 (3) ŵ = 0.07 mm1
β = 93.73 (3)°T = 293 K
V = 2154.5 (15) Å3Needle, red
Z = 40.32 × 0.07 × 0.05 mm
Data collection top
Enraf Nonius CAD-4F
diffractometer
Rint = 0.123
Radiation source: fine focus sealed Philips Mo tubeθmax = 20.0°, θmin = 1.6°
Perpendicular mounted graphite monochromatorh = 05
ω/2θ scansk = 2020
4504 measured reflectionsl = 1515
2001 independent reflections2 standard reflections every 180 min
770 reflections with I > 2σ(I) intensity decay: <0.1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 0.93 w = 1/[σ2(Fo2) + (0.0453P)2]
where P = (Fo2 + 2Fc2)/3
2001 reflections(Δ/σ)max = 0.001
299 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.20 e Å3
Special details top

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
C120.6148 (13)0.2396 (3)0.1595 (5)0.042 (3)
C130.5423 (15)0.2084 (3)0.0811 (5)0.040 (4)
C140.6607 (13)0.2110 (3)0.0113 (5)0.042 (3)
C150.5839 (16)0.1850 (4)0.0667 (5)0.041 (4)
C160.7019 (14)0.1905 (3)0.1390 (6)0.051 (4)
C170.6199 (16)0.1679 (4)0.2125 (6)0.057 (4)
C180.4163 (17)0.1381 (4)0.2184 (6)0.056 (4)
C190.3012 (14)0.1318 (4)0.1489 (6)0.053 (4)
C200.3785 (16)0.1565 (4)0.0709 (5)0.042 (4)
C210.2613 (13)0.1523 (4)0.0011 (5)0.044 (4)
C220.3401 (15)0.1781 (4)0.0738 (5)0.041 (3)
C230.2048 (12)0.1792 (4)0.1499 (5)0.051 (4)
C240.3385 (15)0.1760 (4)0.2316 (5)0.046 (4)
C250.2692 (13)0.1486 (4)0.3007 (5)0.044 (4)
C260.3918 (17)0.1486 (4)0.3781 (5)0.045 (4)
C270.3141 (16)0.1212 (4)0.4510 (6)0.061 (4)
C280.4406 (18)0.1223 (4)0.5247 (6)0.072 (5)
C290.6458 (18)0.1497 (4)0.5283 (6)0.070 (5)
C300.7201 (15)0.1766 (3)0.4591 (6)0.053 (4)
C310.5968 (15)0.1777 (4)0.3824 (5)0.042 (4)
C320.6676 (14)0.2049 (3)0.3096 (6)0.047 (4)
C330.5451 (14)0.2056 (4)0.2362 (5)0.041 (4)
C10.2130 (15)0.0286 (4)0.0147 (5)0.058 (4)
C20.1197 (15)0.0188 (4)0.0683 (6)0.043 (4)
C30.2363 (15)0.0361 (4)0.1381 (6)0.055 (4)
C40.1613 (16)0.0219 (4)0.2206 (6)0.048 (4)
C50.2805 (15)0.0332 (4)0.2906 (6)0.060 (4)
C60.2056 (19)0.0151 (4)0.3678 (6)0.073 (5)
C70.0065 (19)0.0142 (4)0.3821 (6)0.068 (5)
C80.1218 (16)0.0250 (4)0.3167 (6)0.060 (4)
C90.0474 (16)0.0075 (4)0.2343 (6)0.046 (4)
C100.1707 (15)0.0181 (4)0.1646 (6)0.059 (4)
C110.0912 (15)0.0092 (4)0.0831 (6)0.044 (4)
H120.553680.281620.159050.0503*
H12'0.775270.243150.162770.0503*
H140.798290.230780.015190.0505*
H160.839620.210250.135670.0614*
H170.700010.171990.260790.0688*
H180.359130.122510.270500.0675*
H190.166620.110450.153040.0642*
H210.126130.131180.001130.0528*
H230.117200.217240.148640.0612*
H23'0.102770.144030.146470.0612*
H250.132260.128390.296900.0527*
H270.175140.102220.448620.0731*
H280.388190.104260.573380.0858*
H290.733740.149570.579130.0843*
H300.859720.195260.462840.0635*
H320.807180.223520.311800.0557*
H10.351450.047470.024080.0689*
H30.368960.058010.128850.0662*
H50.416170.053860.283630.0720*
H60.291790.022720.413650.0879*
H70.040970.026760.436910.0821*
H80.259740.044040.326490.0716*
H100.316080.032220.174220.0705*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C120.031 (6)0.042 (5)0.054 (6)0.000 (4)0.004 (5)0.007 (5)
C130.035 (6)0.037 (6)0.049 (7)0.000 (5)0.003 (5)0.008 (5)
C140.026 (6)0.034 (5)0.067 (7)0.007 (4)0.007 (6)0.011 (5)
C150.048 (7)0.035 (6)0.042 (7)0.005 (5)0.010 (5)0.009 (5)
C160.044 (6)0.040 (6)0.070 (7)0.001 (5)0.010 (6)0.006 (6)
C170.060 (8)0.060 (7)0.053 (8)0.005 (6)0.010 (6)0.006 (6)
C180.073 (8)0.045 (6)0.051 (7)0.006 (6)0.002 (6)0.002 (5)
C190.046 (7)0.055 (7)0.058 (7)0.003 (5)0.005 (6)0.002 (6)
C200.039 (7)0.041 (6)0.044 (8)0.004 (5)0.007 (5)0.002 (5)
C210.025 (6)0.048 (6)0.059 (7)0.004 (5)0.002 (5)0.011 (5)
C220.037 (6)0.041 (5)0.045 (7)0.004 (5)0.003 (5)0.001 (5)
C230.027 (6)0.069 (6)0.057 (7)0.001 (5)0.001 (5)0.002 (5)
C240.036 (7)0.055 (6)0.047 (7)0.003 (5)0.007 (5)0.001 (5)
C250.019 (5)0.061 (7)0.053 (7)0.008 (5)0.007 (5)0.007 (5)
C260.059 (8)0.035 (6)0.041 (7)0.008 (6)0.001 (6)0.004 (5)
C270.064 (8)0.055 (6)0.064 (7)0.009 (6)0.005 (7)0.002 (6)
C280.078 (9)0.080 (8)0.057 (8)0.013 (7)0.006 (6)0.001 (6)
C290.089 (10)0.062 (7)0.057 (8)0.006 (6)0.017 (7)0.010 (6)
C300.059 (7)0.041 (6)0.056 (7)0.005 (5)0.014 (6)0.006 (5)
C310.031 (6)0.045 (6)0.049 (7)0.003 (5)0.002 (5)0.009 (5)
C320.035 (6)0.043 (6)0.062 (7)0.003 (5)0.003 (6)0.012 (5)
C330.032 (6)0.039 (6)0.050 (7)0.008 (5)0.002 (5)0.004 (5)
C10.043 (7)0.093 (8)0.036 (7)0.016 (6)0.002 (6)0.023 (6)
C20.029 (7)0.039 (6)0.062 (9)0.005 (5)0.010 (5)0.003 (5)
C30.039 (7)0.063 (7)0.063 (8)0.002 (5)0.003 (6)0.011 (6)
C40.047 (8)0.029 (6)0.067 (9)0.004 (5)0.003 (6)0.005 (5)
C50.057 (7)0.063 (7)0.062 (8)0.001 (5)0.021 (7)0.018 (6)
C60.081 (9)0.088 (9)0.051 (9)0.003 (7)0.009 (7)0.001 (6)
C70.078 (9)0.067 (8)0.059 (8)0.015 (7)0.005 (7)0.009 (6)
C80.060 (7)0.064 (7)0.053 (8)0.009 (6)0.015 (6)0.015 (6)
C90.048 (7)0.038 (6)0.051 (8)0.009 (5)0.003 (6)0.001 (5)
C100.027 (6)0.089 (8)0.061 (8)0.007 (5)0.012 (6)0.027 (6)
C110.026 (7)0.052 (6)0.053 (8)0.003 (5)0.002 (6)0.013 (5)
Geometric parameters (Å, º) top
C12—C131.475 (11)C18—H180.9498
C12—C331.524 (11)C19—H190.9496
C13—C141.378 (12)C21—H210.9505
C13—C221.409 (13)C23—H230.9890
C14—C151.428 (11)C23—H23'0.9909
C15—C161.415 (13)C25—H250.9505
C15—C201.408 (14)C27—H270.9497
C16—C171.347 (13)C28—H280.9507
C17—C181.411 (14)C29—H290.9504
C18—C191.368 (14)C30—H300.9502
C19—C201.418 (13)C32—H320.9498
C20—C211.406 (12)C1—C21.434 (13)
C21—C221.358 (12)C1—C111.434 (13)
C22—C231.524 (12)C2—C31.422 (13)
C23—C241.506 (12)C2—C11i1.442 (13)
C24—C251.354 (12)C3—C41.410 (14)
C24—C331.425 (13)C4—C51.405 (14)
C25—C261.413 (12)C4—C91.441 (14)
C26—C271.425 (13)C5—C61.354 (14)
C26—C311.411 (14)C6—C71.389 (16)
C27—C281.375 (14)C7—C81.376 (14)
C28—C291.396 (15)C8—C91.425 (14)
C29—C301.362 (13)C9—C101.413 (14)
C30—C311.405 (13)C10—C11i1.382 (14)
C31—C321.406 (12)C1—H10.9504
C32—C331.358 (12)C3—H30.9502
C12—H120.9903C5—H50.9499
C12—H12'0.9900C6—H60.9505
C14—H140.9497C7—H70.9501
C16—H160.9501C8—H80.9499
C17—H170.9506C10—H100.9505
C5···C31ii3.580 (13)H10···C18iii2.8983
C5···C26ii3.571 (13)H10···C17iii3.0417
C10···C17iii3.577 (13)H10···H1i2.4591
C17···C10iii3.577 (13)H10···H82.5069
C26···C5iv3.571 (13)H12···C233.0967
C31···C5iv3.580 (13)H12'···H23iv2.2076
C1···H213.0591H12'···H322.4281
C4···H19i3.0823H12'···H142.4001
C6···H28v3.0115H12'···C23iv3.0109
C7···H272.9465H14···H12'2.4001
C7···H7v3.0629H14···H162.4944
C9···H19i2.8737H16···C32viii2.9176
C10···H19i2.8913H16···H142.4944
C11···H192.9820H16···C31viii2.9162
C12···H233.0989H16···C33viii3.0899
C13···H30vi3.0017H18···H28ix2.5578
C14···H30vi2.8347H19···C112.9820
C15···H1iv3.0955H19···C10i2.8913
C15···H30vi3.0057H19···H212.5109
C17···H32vi3.0933H19···C4i3.0823
C17···H10iii3.0417H19···C9i2.8737
C18···H10iii2.8983H21···H192.5109
C20···H1iv2.9704H21···H23'2.4019
C23···H123.0967H21···C13.0591
C23···H12'ii3.0109H23···C123.0989
C25···H5iv2.8584H23···H12'ii2.2076
C26···H5iv2.8644H23'···H252.4362
C31···H16vii2.9162H23'···H212.4019
C32···H16vii2.9176H25···H23'2.4362
C33···H16vii3.0899H25···H272.5011
H1···C15ii3.0955H27···C72.9465
H1···H10i2.4591H27···H252.5011
H1···C20ii2.9704H28···H18x2.5578
H1···H32.4775H28···C6v3.0115
H3···H52.5245H30···C15xi3.0057
H3···H12.4775H30···H322.5046
H5···C25ii2.8584H30···C14xi2.8347
H5···C26ii2.8644H30···C13xi3.0017
H5···H32.5245H32···H302.5046
H7···C7v3.0629H32···C17xi3.0933
H7···H7v2.4209H32···H12'2.4281
H8···H102.5069
C13—C12—C33112.4 (6)C20—C21—H21119.76
C12—C13—C14121.9 (7)C22—C21—H21119.78
C12—C13—C22120.3 (7)C22—C23—H23108.85
C14—C13—C22117.6 (7)C22—C23—H23'108.75
C13—C14—C15122.3 (8)C24—C23—H23108.89
C14—C15—C16121.9 (8)C24—C23—H23'108.78
C14—C15—C20117.6 (8)H23—C23—H23'107.70
C16—C15—C20120.4 (8)C24—C25—H25118.55
C15—C16—C17120.3 (8)C26—C25—H25118.58
C16—C17—C18120.6 (9)C26—C27—H27119.99
C17—C18—C19119.8 (9)C28—C27—H27120.10
C18—C19—C20121.4 (8)C27—C28—H28119.84
C15—C20—C19117.3 (8)C29—C28—H28119.88
C15—C20—C21119.8 (8)C28—C29—H29119.91
C19—C20—C21122.8 (8)C30—C29—H29119.97
C20—C21—C22120.5 (8)C29—C30—H30118.93
C13—C22—C21122.1 (8)C31—C30—H30118.94
C13—C22—C23116.9 (7)C31—C32—H32118.60
C21—C22—C23120.9 (8)C33—C32—H32118.58
C22—C23—C24113.7 (7)C2—C1—C11118.1 (8)
C23—C24—C25123.5 (8)C1—C2—C3120.1 (8)
C23—C24—C33117.4 (7)C1—C2—C11i121.3 (8)
C25—C24—C33119.1 (8)C3—C2—C11i118.6 (9)
C24—C25—C26122.9 (8)C2—C3—C4122.1 (8)
C25—C26—C27122.3 (9)C3—C4—C5123.9 (9)
C25—C26—C31118.0 (8)C3—C4—C9118.4 (9)
C27—C26—C31119.7 (8)C5—C4—C9117.6 (9)
C26—C27—C28119.9 (9)C4—C5—C6121.2 (9)
C27—C28—C29120.3 (9)C5—C6—C7122.0 (9)
C28—C29—C30120.1 (9)C6—C7—C8119.8 (9)
C29—C30—C31122.1 (9)C7—C8—C9119.9 (9)
C26—C31—C30117.8 (8)C4—C9—C8119.4 (9)
C26—C31—C32118.3 (8)C4—C9—C10118.2 (9)
C30—C31—C32123.9 (8)C8—C9—C10122.4 (9)
C31—C32—C33122.8 (8)C9—C10—C11i123.5 (9)
C12—C33—C24118.4 (7)C1—C11—C2i120.6 (8)
C12—C33—C32122.5 (8)C1—C11—C10i120.9 (8)
C24—C33—C32119.0 (8)C2i—C11—C10i118.4 (9)
C13—C12—H12109.05C2—C1—H1120.91
C13—C12—H12'109.11C11—C1—H1121.01
C33—C12—H12109.19C2—C3—H3118.94
C33—C12—H12'109.17C4—C3—H3118.92
H12—C12—H12'107.83C4—C5—H5119.40
C13—C14—H14118.86C6—C5—H5119.42
C15—C14—H14118.79C5—C6—H6119.00
C15—C16—H16119.80C7—C6—H6118.97
C17—C16—H16119.86C6—C7—H7120.08
C16—C17—H17119.74C8—C7—H7120.07
C18—C17—H17119.69C7—C8—H8120.06
C17—C18—H18120.09C9—C8—H8120.09
C19—C18—H18120.08C9—C10—H10118.29
C18—C19—H19119.26C11i—C10—H10118.16
C20—C19—H19119.33
C33—C12—C13—C14148.4 (7)C25—C26—C31—C30178.8 (8)
C33—C12—C13—C2235.8 (10)C25—C26—C31—C320.1 (12)
C13—C12—C33—C2436.4 (10)C27—C26—C31—C302.0 (13)
C13—C12—C33—C32146.7 (8)C27—C26—C31—C32179.3 (8)
C12—C13—C14—C15175.0 (7)C26—C27—C28—C290.5 (14)
C22—C13—C14—C150.8 (11)C27—C28—C29—C301.3 (14)
C12—C13—C22—C21175.6 (8)C28—C29—C30—C310.4 (13)
C12—C13—C22—C230.3 (11)C29—C30—C31—C261.3 (12)
C14—C13—C22—C210.3 (12)C29—C30—C31—C32179.9 (8)
C14—C13—C22—C23176.2 (7)C26—C31—C32—C331.6 (12)
C13—C14—C15—C16176.9 (7)C30—C31—C32—C33179.7 (8)
C13—C14—C15—C200.6 (12)C31—C32—C33—C12174.9 (7)
C14—C15—C16—C17176.9 (8)C31—C32—C33—C241.9 (12)
C20—C15—C16—C170.7 (12)C11—C1—C2—C3178.7 (8)
C14—C15—C20—C19178.8 (8)C11—C1—C2—C11i0.6 (13)
C14—C15—C20—C212.6 (13)C2—C1—C11—C2i0.6 (13)
C16—C15—C20—C192.5 (13)C2—C1—C11—C10i179.1 (8)
C16—C15—C20—C21178.9 (8)C1—C2—C3—C4173.5 (8)
C15—C16—C17—C180.4 (13)C11i—C2—C3—C45.7 (13)
C16—C17—C18—C190.3 (13)C1—C2—C11i—C10179.2 (8)
C17—C18—C19—C202.2 (14)C1—C2—C11i—C1i0.6 (13)
C18—C19—C20—C153.2 (13)C3—C2—C11i—C100.1 (13)
C18—C19—C20—C21178.2 (9)C3—C2—C11i—C1i178.7 (8)
C15—C20—C21—C223.1 (13)C2—C3—C4—C5174.0 (9)
C19—C20—C21—C22178.3 (8)C2—C3—C4—C94.2 (13)
C20—C21—C22—C131.7 (13)C3—C4—C5—C6175.9 (9)
C20—C21—C22—C23174.1 (8)C9—C4—C5—C62.4 (13)
C13—C22—C23—C2435.6 (11)C3—C4—C9—C8176.9 (8)
C21—C22—C23—C24148.5 (8)C3—C4—C9—C102.8 (13)
C22—C23—C24—C25147.9 (9)C5—C4—C9—C81.4 (13)
C22—C23—C24—C3334.5 (11)C5—C4—C9—C10178.9 (8)
C23—C24—C25—C26176.7 (8)C4—C5—C6—C71.4 (14)
C33—C24—C25—C260.8 (13)C5—C6—C7—C80.7 (14)
C23—C24—C33—C121.4 (12)C6—C7—C8—C91.6 (14)
C23—C24—C33—C32178.4 (8)C7—C8—C9—C40.6 (13)
C25—C24—C33—C12176.3 (8)C7—C8—C9—C10179.2 (9)
C25—C24—C33—C320.7 (13)C4—C9—C10—C11i8.7 (13)
C24—C25—C26—C27178.0 (9)C8—C9—C10—C11i171.0 (9)
C24—C25—C26—C311.1 (13)C9—C10—C11i—C27.2 (13)
C25—C26—C27—C28179.7 (9)C9—C10—C11i—C1i171.4 (8)
C31—C26—C27—C281.1 (13)
Symmetry codes: (i) x, y, z; (ii) x1, y, z; (iii) x+1, y, z; (iv) x+1, y, z; (v) x, y, z+1; (vi) x1/2, y+1/2, z1/2; (vii) x1/2, y+1/2, z+1/2; (viii) x+1/2, y+1/2, z1/2; (ix) x, y, z1; (x) x, y, z+1; (xi) x+1/2, y+1/2, z+1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds