In the title compound, C
10H
8O
2, the four symmetry-related molecules are connected to each other through O—H
O hydrogen bonds to form a helical chain along the
b axis. The interconnected system is further extended along the
c axis through O—H
O hydrogen bonds to form a two-dimensional network. Unlike its
trans isomer, no C—H
O or C—H
π interactions are observed in the crystal structure.
Supporting information
CCDC reference: 259121
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.059
- wR factor = 0.154
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.97 Deg.
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc.
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999).
(
Z)-3,6-Diethynyl-3,6-dihydroxycyclohexa-1,4-diene
top
Crystal data top
C10H8O2 | Dx = 1.158 Mg m−3 |
Mr = 160.16 | Melting point: 124-126 °C K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.598 (2) Å | Cell parameters from 25 reflections |
b = 6.2646 (10) Å | θ = 10–15° |
c = 14.153 (3) Å | µ = 0.08 mm−1 |
β = 102.06 (2)° | T = 293 K |
V = 918.9 (3) Å3 | Plate, colourless |
Z = 4 | 0.3 × 0.2 × 0.2 mm |
F(000) = 336 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 730 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.048 |
Graphite monochromator | θmax = 25.0°, θmin = 2.9° |
ω–2θ scans | h = 0→12 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→7 |
Tmin = 0.941, Tmax = 0.989 | l = −16→16 |
1712 measured reflections | 2 standard reflections every 60 min |
1617 independent reflections | intensity decay: none |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.154 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0602P)2] where P = (Fo2 + 2Fc2)/3 |
1617 reflections | (Δ/σ)max < 0.001 |
127 parameters | Δρmax = 0.29 e Å−3 |
4 restraints | Δρmin = −0.19 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. |
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 | Uiso*/Ueq | |
C1 | 0.7342 (3) | 0.2621 (6) | 0.7495 (3) | 0.0520 (9) | |
C2 | 0.6918 (3) | 0.0387 (6) | 0.7243 (2) | 0.0456 (9) | |
C3 | 0.6383 (3) | −0.0649 (6) | 0.8033 (3) | 0.0575 (10) | |
C4 | 0.6516 (4) | 0.0164 (7) | 0.8903 (3) | 0.0661 (11) | |
C5 | 0.7126 (3) | 0.2264 (7) | 0.9197 (2) | 0.0619 (11) | |
C6 | 0.7450 (4) | 0.3448 (6) | 0.8364 (3) | 0.0620 (10) | |
C7 | 0.8007 (4) | −0.0879 (6) | 0.7055 (2) | 0.0589 (10) | |
C8 | 0.8867 (5) | −0.1847 (7) | 0.6899 (3) | 0.0927 (16) | |
C9 | 0.8314 (4) | 0.2037 (6) | 0.9943 (3) | 0.0683 (11) | |
C10 | 0.9279 (4) | 0.1899 (7) | 1.0515 (3) | 0.0918 (15) | |
O1 | 0.5881 (2) | 0.0397 (4) | 0.64040 (16) | 0.0634 (8) | |
O2 | 0.6264 (3) | 0.3535 (5) | 0.96314 (18) | 0.0969 (11) | |
H1 | 0.756 (3) | 0.344 (4) | 0.6977 (14) | 0.062 (10)* | |
H1' | 0.6133 | 0.0927 | 0.5947 | 0.14 (2)* | |
H2' | 0.5604 | 0.3784 | 0.9228 | 0.15 (2)* | |
H3 | 0.597 (3) | −0.200 (2) | 0.785 (2) | 0.055 (10)* | |
H4 | 0.613 (3) | −0.065 (5) | 0.935 (2) | 0.078 (12)* | |
H6 | 0.763 (3) | 0.4945 (14) | 0.845 (2) | 0.067 (12)* | |
H8 | 0.9560 | −0.2628 | 0.6772 | 0.111* | |
H10 | 1.0048 | 0.1789 | 1.0970 | 0.110* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.058 (2) | 0.052 (3) | 0.046 (2) | −0.0053 (19) | 0.0095 (18) | 0.0053 (19) |
C2 | 0.0437 (18) | 0.062 (3) | 0.0311 (17) | −0.0071 (18) | 0.0069 (15) | 0.0009 (17) |
C3 | 0.057 (2) | 0.062 (3) | 0.053 (2) | −0.009 (2) | 0.0110 (18) | 0.004 (2) |
C4 | 0.063 (2) | 0.095 (3) | 0.043 (2) | 0.005 (2) | 0.0173 (19) | 0.016 (2) |
C5 | 0.059 (2) | 0.087 (3) | 0.039 (2) | 0.026 (2) | 0.0079 (18) | −0.007 (2) |
C6 | 0.077 (3) | 0.053 (3) | 0.052 (2) | 0.011 (2) | 0.0035 (19) | −0.005 (2) |
C7 | 0.061 (2) | 0.065 (3) | 0.054 (2) | 0.000 (2) | 0.0185 (19) | −0.005 (2) |
C8 | 0.086 (3) | 0.092 (4) | 0.108 (4) | 0.014 (3) | 0.036 (3) | −0.012 (3) |
C9 | 0.073 (3) | 0.084 (3) | 0.046 (2) | 0.030 (2) | 0.007 (2) | −0.008 (2) |
C10 | 0.080 (3) | 0.113 (4) | 0.074 (3) | 0.032 (3) | −0.004 (2) | −0.011 (3) |
O1 | 0.0512 (13) | 0.099 (2) | 0.0368 (13) | −0.0170 (15) | 0.0023 (11) | 0.0037 (14) |
O2 | 0.0849 (19) | 0.159 (3) | 0.0422 (14) | 0.067 (2) | 0.0024 (14) | −0.0175 (17) |
Geometric parameters (Å, º) top
C1—C6 | 1.316 (5) | C5—O2 | 1.442 (4) |
C1—C2 | 1.490 (5) | C5—C9 | 1.470 (5) |
C1—H1 | 0.96 (2) | C5—C6 | 1.493 (5) |
C2—O1 | 1.439 (4) | C6—H6 | 0.960 (12) |
C2—C7 | 1.469 (5) | C7—C8 | 1.154 (5) |
C2—C3 | 1.504 (4) | C8—H8 | 0.9300 |
C3—C4 | 1.312 (5) | C9—C10 | 1.168 (5) |
C3—H3 | 0.963 (18) | C10—H10 | 0.9300 |
C4—C5 | 1.487 (5) | O1—H1' | 0.8200 |
C4—H4 | 0.97 (3) | O2—H2' | 0.8200 |
| | | |
C6—C1—C2 | 123.8 (3) | O2—C5—C9 | 105.7 (3) |
C6—C1—H1 | 120.9 (19) | O2—C5—C4 | 109.3 (3) |
C2—C1—H1 | 115.2 (18) | C9—C5—C4 | 111.9 (3) |
O1—C2—C7 | 110.3 (3) | O2—C5—C6 | 109.4 (3) |
O1—C2—C1 | 109.5 (3) | C9—C5—C6 | 108.2 (3) |
C7—C2—C1 | 110.0 (3) | C4—C5—C6 | 112.1 (3) |
O1—C2—C3 | 105.9 (3) | C1—C6—C5 | 123.6 (4) |
C7—C2—C3 | 109.5 (3) | C1—C6—H6 | 119 (2) |
C1—C2—C3 | 111.6 (3) | C5—C6—H6 | 117 (2) |
C4—C3—C2 | 123.2 (4) | C8—C7—C2 | 178.9 (4) |
C4—C3—H3 | 123.0 (18) | C7—C8—H8 | 180.0 |
C2—C3—H3 | 113.8 (18) | C10—C9—C5 | 177.6 (5) |
C3—C4—C5 | 124.1 (4) | C9—C10—H10 | 180.0 |
C3—C4—H4 | 115 (2) | C2—O1—H1' | 109.5 |
C5—C4—H4 | 120 (2) | C5—O2—H2' | 109.5 |
| | | |
C6—C1—C2—O1 | 128.3 (3) | C3—C4—C5—O2 | 127.4 (4) |
C6—C1—C2—C7 | −110.4 (4) | C3—C4—C5—C9 | −115.8 (4) |
C6—C1—C2—C3 | 11.4 (5) | C3—C4—C5—C6 | 5.9 (5) |
O1—C2—C3—C4 | −131.7 (4) | C2—C1—C6—C5 | −1.8 (6) |
C7—C2—C3—C4 | 109.4 (4) | O2—C5—C6—C1 | −128.7 (4) |
C1—C2—C3—C4 | −12.7 (5) | C9—C5—C6—C1 | 116.6 (4) |
C2—C3—C4—C5 | 4.4 (6) | C4—C5—C6—C1 | −7.2 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1′···O2i | 0.82 | 1.93 | 2.708 (3) | 159 |
O2—H2′···O1ii | 0.82 | 1.93 | 2.699 (4) | 157 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, y+1/2, −z+3/2. |