1,2-Di-3-thienyl-2-hydroxy­ethano­ne (3,3'-thenoin)

The title compound, C₁₀H₈O₂S₂, is the 3-thienyl symmetric analog of benzoin. 3,3'-Thenoin can be synthesized in good yield utilizing the benzoin condensation reaction (starting with 3-thio­phene­carbox­aldehyde). The crystal structure of 3,3'-thenoin has been determined at room temperature. There are two independent mol­ecules per asymmetric unit and each has a thienyl ring flip disorder involving one of the two rings in each mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.063
• wR factor = 0.194
• Data-to-parameter ratio = 12.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



THETM_01  Alert C The value of sine(theta_max)/wavelength is less than 0.590
          Calculated sin(theta_max)/wavelength =    0.5882

General Notes



CELLZ_01
         From the CIF: _cell_formula_units_Z    8
         From the CIF: _chemical_formula_sum  C10 H8 O2 S2
         TEST: Compare cell contents of formula and atom_site data

         atom    Z*formula  cif sites diff
         C         80.00     80.03   -0.03
         H         64.00     64.02   -0.02
         O         16.00     16.00    0.00
         S         16.00     16.01   -0.01
          Difference between formula and atom_site contents detected.
          ALERT: check formula stoichiometry or atom site occupancies.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SHELXTL-Plus (Sheldrick, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

1,2-di-3-thienyl-2-hydroxyethanone

Crystal data

C10H8O2S2	Dx = 1.489 Mg m^−3
Mr = 224.28	Melting point: 108-109° K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.2503 (17) Å	Cell parameters from 12182 reflections
b = 16.421 (3) Å	θ = 1.9–24.7°
c = 15.041 (3) Å	µ = 0.50 mm^−1
β = 100.86 (3)°	T = 293 K
V = 2001.2 (7) Å^3	Needle, colorless
Z = 8	0.3 × 0.1 × 0.05 mm
F(000) = 928

Data collection

Siemens SMART P3/512CCD diffractometer	2086 reflections with I > 2s(I)
Radiation source: fine-focus sealed tube	Rint = 0.059
Graphite monochromator	θmax = 24.7°, θmin = 1.9°
ω scans	h = −9→9
11939 measured reflections	k = −19→19
3412 independent reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.194	H-atom parameters constrained
S = 1.14	w = 1/[σ^2(Fo^2) + (0.1P)^2] where = P = (Fo^2 + 2Fc^2)/3
3412 reflections	(Δ/σ)max = 0.007
269 parameters	Δρmax = 0.34 e Å^−3
22 restraints	Δρmin = −0.35 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1A	0.0763 (2)	0.26808 (12)	0.1338 (2)	0.0753 (7)	0.890 (5)
C2A	0.2432 (5)	0.2116 (3)	0.1261 (3)	0.0576 (12)	0.890 (5)
H2AA	0.2486	0.1554	0.1340	0.069*	0.890 (5)
C3A	0.3703 (5)	0.2579 (2)	0.1067 (2)	0.0415 (10)	0.890 (5)
C4A	0.3281 (6)	0.3406 (3)	0.0977 (3)	0.0603 (13)	0.890 (5)
H4AA	0.3997	0.3810	0.0853	0.072*	0.890 (5)
C5A	0.1709 (14)	0.3555 (6)	0.1093 (8)	0.069 (3)	0.890 (5)
H5AA	0.1216	0.4066	0.1045	0.083*	0.890 (5)
S1B	0.142 (3)	0.3573 (15)	0.124 (2)	0.0753 (7)	0.111 (5)
C2B	0.3281 (6)	0.3406 (3)	0.0977 (3)	0.0603 (13)	0.111 (5)
H2BA	0.3943	0.3808	0.0796	0.072*	0.111 (5)
C3B	0.3703 (5)	0.2579 (2)	0.1067 (2)	0.0415 (10)	0.111 (5)
C4B	0.2432 (5)	0.2116 (3)	0.1261 (3)	0.0576 (12)	0.111 (5)
H4BA	0.2484	0.1552	0.1312	0.069*	0.111 (5)
C5B	0.109 (6)	0.256 (2)	0.137 (7)	0.069 (3)	0.111 (5)
H5BA	0.0121	0.2335	0.1499	0.083*	0.111 (5)
S4A	0.8768 (4)	0.53846 (15)	0.11860 (11)	0.0674 (7)	0.856 (4)
C17A	0.9452 (5)	0.5456 (3)	0.2321 (3)	0.0548 (12)	0.856 (4)
H17A	1.0146	0.5866	0.2596	0.066*	0.856 (4)
C18A	0.8865 (4)	0.4840 (2)	0.2783 (3)	0.0392 (10)	0.856 (4)
C19A	0.7848 (5)	0.4306 (2)	0.2189 (3)	0.0468 (11)	0.856 (4)
H19A	0.7360	0.3848	0.2389	0.056*	0.856 (4)
C20A	0.7636 (13)	0.4515 (6)	0.1295 (5)	0.049 (2)	0.856 (4)
H20A	0.6987	0.4234	0.0820	0.059*	0.856 (4)
S4B	0.772 (3)	0.4614 (15)	0.1093 (10)	0.0674 (7)	0.145 (4)
C17B	0.7848 (5)	0.4306 (2)	0.2189 (3)	0.0468 (11)	0.145 (4)
H17B	0.7321	0.3851	0.2368	0.056*	0.145 (4)
C18B	0.8865 (4)	0.4840 (2)	0.2783 (3)	0.0392 (10)	0.145 (4)
C19B	0.9452 (5)	0.5456 (3)	0.2321 (3)	0.0548 (12)	0.145 (4)
H19B	1.0142	0.5858	0.2618	0.066*	0.145 (4)
C20B	0.898 (8)	0.545 (3)	0.1406 (14)	0.049 (2)	0.145 (4)
H20B	0.9277	0.5835	0.1012	0.059*	0.145 (4)
C1	0.5301 (5)	0.2269 (2)	0.0935 (2)	0.0400 (10)
O1	0.6288 (4)	0.26981 (17)	0.0638 (2)	0.0553 (8)
C6	0.5779 (5)	0.1398 (2)	0.1190 (3)	0.0414 (10)
H6A	0.4872	0.1036	0.0925	0.050*
O2	0.7224 (4)	0.11864 (17)	0.0842 (2)	0.0586 (8)
H2A	0.6966	0.0885	0.0403	0.088*
S2	0.61484 (16)	0.07675 (8)	0.37966 (8)	0.0619 (4)
C7	0.5485 (5)	0.0702 (2)	0.2660 (3)	0.0464 (11)
H7A	0.4769	0.0301	0.2382	0.056*
C8	0.6116 (5)	0.1299 (2)	0.2201 (3)	0.0374 (9)
C9	0.7170 (5)	0.1831 (2)	0.2809 (3)	0.0460 (10)
H9A	0.7704	0.2279	0.2620	0.055*
C10	0.7306 (5)	0.1611 (3)	0.3686 (3)	0.0492 (11)
H10A	0.7948	0.1885	0.4169	0.059*
C11	0.9785 (5)	0.3886 (2)	0.4042 (3)	0.0420 (10)
O3	0.8874 (4)	0.34420 (18)	0.4366 (2)	0.0591 (8)
S3	1.42651 (16)	0.35210 (11)	0.35236 (10)	0.0824 (5)
C12	1.2630 (5)	0.4071 (3)	0.3690 (3)	0.0622 (13)
H12A	1.2590	0.4637	0.3670	0.075*
C13	1.1374 (5)	0.3596 (3)	0.3855 (2)	0.0409 (10)
C14	1.1791 (5)	0.2756 (3)	0.3858 (3)	0.0543 (12)
H14A	1.1092	0.2342	0.3977	0.065*
C15	1.3346 (5)	0.2617 (3)	0.3666 (3)	0.0497 (11)
H15A	1.3815	0.2107	0.3622	0.060*
C16	0.9245 (5)	0.4760 (2)	0.3789 (3)	0.0434 (10)
H16A	1.0146	0.5133	0.4034	0.052*
O4	0.7839 (4)	0.49583 (18)	0.41610 (19)	0.0616 (9)
H4A	0.7776	0.4646	0.4579	0.092*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0465 (10)	0.1006 (16)	0.0805 (12)	0.0124 (9)	0.0166 (10)	−0.0003 (12)
C2A	0.054 (3)	0.055 (3)	0.063 (3)	0.000 (2)	0.010 (2)	−0.001 (2)
C3A	0.041 (2)	0.047 (3)	0.036 (2)	0.002 (2)	0.0060 (18)	−0.0006 (18)
C4A	0.057 (3)	0.048 (3)	0.076 (3)	0.011 (2)	0.015 (2)	0.003 (2)
C5A	0.077 (7)	0.063 (4)	0.070 (6)	0.026 (4)	0.020 (4)	0.005 (3)
S1B	0.0465 (10)	0.1006 (16)	0.0805 (12)	0.0124 (9)	0.0166 (10)	−0.0003 (12)
C2B	0.057 (3)	0.048 (3)	0.076 (3)	0.011 (2)	0.015 (2)	0.003 (2)
C3B	0.041 (2)	0.047 (3)	0.036 (2)	0.002 (2)	0.0060 (18)	−0.0006 (18)
C4B	0.054 (3)	0.055 (3)	0.063 (3)	0.000 (2)	0.010 (2)	−0.001 (2)
C5B	0.077 (7)	0.063 (4)	0.070 (6)	0.026 (4)	0.020 (4)	0.005 (3)
S4A	0.0791 (16)	0.0668 (13)	0.0583 (11)	0.0088 (9)	0.0179 (11)	0.0202 (10)
C17A	0.061 (3)	0.045 (3)	0.058 (3)	−0.004 (2)	0.010 (2)	0.003 (2)
C18A	0.035 (2)	0.034 (2)	0.048 (2)	0.0060 (18)	0.0081 (18)	0.0024 (19)
C19A	0.046 (3)	0.044 (3)	0.050 (3)	−0.001 (2)	0.009 (2)	−0.004 (2)
C20A	0.042 (3)	0.049 (5)	0.058 (5)	−0.004 (3)	0.011 (4)	−0.009 (4)
S4B	0.0791 (16)	0.0668 (13)	0.0583 (11)	0.0088 (9)	0.0179 (11)	0.0202 (10)
C17B	0.046 (3)	0.044 (3)	0.050 (3)	−0.001 (2)	0.009 (2)	−0.004 (2)
C18B	0.035 (2)	0.034 (2)	0.048 (2)	0.0060 (18)	0.0081 (18)	0.0024 (19)
C19B	0.061 (3)	0.045 (3)	0.058 (3)	−0.004 (2)	0.010 (2)	0.003 (2)
C20B	0.042 (3)	0.049 (5)	0.058 (5)	−0.004 (3)	0.011 (4)	−0.009 (4)
C1	0.045 (2)	0.040 (2)	0.035 (2)	0.002 (2)	0.0074 (19)	0.0023 (18)
O1	0.0530 (19)	0.0459 (18)	0.071 (2)	−0.0030 (15)	0.0212 (16)	0.0101 (15)
C6	0.043 (2)	0.037 (2)	0.046 (2)	0.0037 (19)	0.0121 (19)	−0.0033 (18)
O2	0.065 (2)	0.055 (2)	0.0620 (19)	0.0152 (16)	0.0281 (16)	−0.0029 (15)
S2	0.0756 (9)	0.0600 (8)	0.0513 (8)	0.0026 (7)	0.0152 (6)	0.0115 (6)
C7	0.051 (3)	0.032 (2)	0.057 (3)	−0.0049 (19)	0.013 (2)	0.0006 (19)
C8	0.037 (2)	0.030 (2)	0.047 (2)	0.0071 (18)	0.0137 (18)	0.0011 (18)
C9	0.045 (2)	0.040 (3)	0.055 (3)	−0.004 (2)	0.014 (2)	−0.001 (2)
C10	0.040 (2)	0.050 (3)	0.056 (3)	0.004 (2)	0.005 (2)	−0.007 (2)
C11	0.043 (2)	0.047 (3)	0.037 (2)	0.006 (2)	0.0099 (19)	−0.0022 (19)
O3	0.0587 (19)	0.054 (2)	0.072 (2)	0.0069 (16)	0.0310 (16)	0.0145 (16)
S3	0.0525 (8)	0.1061 (12)	0.0931 (11)	0.0141 (8)	0.0254 (7)	0.0047 (9)
C12	0.053 (3)	0.060 (3)	0.076 (3)	0.002 (2)	0.019 (2)	0.007 (2)
C13	0.038 (2)	0.048 (3)	0.036 (2)	0.000 (2)	0.0059 (18)	0.0021 (18)
C14	0.057 (3)	0.043 (3)	0.063 (3)	0.008 (2)	0.011 (2)	0.001 (2)
C15	0.047 (3)	0.048 (3)	0.053 (3)	0.019 (2)	0.008 (2)	−0.001 (2)
C16	0.049 (3)	0.038 (2)	0.044 (2)	0.0046 (19)	0.0103 (19)	−0.0038 (18)
O4	0.070 (2)	0.062 (2)	0.0587 (19)	0.0252 (17)	0.0269 (16)	0.0074 (15)

Geometric parameters (Å, º)

S1A—C5A	1.707 (9)	C6—C8	1.501 (5)
S1A—C2A	1.683 (5)	C6—H6A	0.9800
C2A—C3A	1.370 (5)	O2—H2A	0.8200
C2A—H2AA	0.9300	S2—C7	1.697 (4)
C3A—C4A	1.403 (5)	S2—C10	1.708 (4)
C3A—C1	1.461 (5)	C7—C8	1.358 (5)
C4A—C5A	1.362 (10)	C7—H7A	0.9300
C4A—H4AA	0.9300	C8—C9	1.434 (5)
C5A—H5AA	0.9300	C9—C10	1.352 (6)
S1B—C5B	1.709 (19)	C9—H9A	0.9300
C5B—H5BA	0.9300	C10—H10A	0.9300
S4A—C17A	1.698 (5)	C11—O3	1.214 (5)
S4A—C20A	1.731 (8)	C11—C13	1.471 (5)
C17A—C18A	1.366 (5)	C11—C16	1.529 (5)
C17A—H17A	0.9300	S3—C12	1.681 (5)
C18A—C19A	1.410 (5)	S3—C15	1.699 (4)
C18A—C16	1.492 (5)	C12—C13	1.357 (6)
C19A—C20A	1.366 (9)	C12—H12A	0.9300
C19A—H19A	0.9300	C13—C14	1.422 (6)
C20A—H20A	0.9300	C14—C15	1.386 (5)
S4B—C20B	1.732 (19)	C14—H14A	0.9300
C20B—H20B	0.9300	C15—H15A	0.9300
C1—O1	1.223 (4)	C16—O4	1.418 (5)
C1—C6	1.515 (5)	C16—H16A	0.9800
C6—O2	1.433 (4)	O4—H4A	0.8200
C5A—S1A—C2A	92.0 (4)	C6—O2—H2A	109.5
C3A—C2A—S1A	112.2 (3)	C7—S2—C10	91.9 (2)
C3A—C2A—H2AA	123.9	C8—C7—S2	112.6 (3)
S1A—C2A—H2AA	123.9	C8—C7—H7A	123.7
C2A—C3A—C4A	111.8 (4)	S2—C7—H7A	123.7
C2A—C3A—C1	125.6 (4)	C7—C8—C9	111.1 (4)
C4A—C3A—C1	122.5 (4)	C7—C8—C6	125.2 (4)
C5A—C4A—C3A	112.7 (6)	C9—C8—C6	123.7 (3)
C5A—C4A—H4AA	123.6	C10—C9—C8	112.9 (4)
C3A—C4A—H4AA	123.6	C10—C9—H9A	123.6
C4A—C5A—S1A	111.2 (6)	C8—C9—H9A	123.6
C4A—C5A—H5AA	124.4	C9—C10—S2	111.5 (3)
S1A—C5A—H5AA	124.4	C9—C10—H10A	124.3
S1B—C5B—H5BA	124.7	S2—C10—H10A	124.3
C17A—S4A—C20A	92.5 (3)	O3—C11—C13	121.6 (4)
C18A—C17A—S4A	112.2 (3)	O3—C11—C16	119.4 (4)
C18A—C17A—H17A	123.9	C13—C11—C16	119.0 (4)
S4A—C17A—H17A	123.9	C12—S3—C15	93.5 (2)
C17A—C18A—C19A	111.3 (4)	C13—C12—S3	112.3 (4)
C17A—C18A—C16	123.6 (3)	C13—C12—H12A	123.9
C19A—C18A—C16	125.0 (4)	S3—C12—H12A	123.9
C20A—C19A—C18A	114.7 (5)	C12—C13—C14	111.5 (4)
C20A—C19A—H19A	122.7	C12—C13—C11	125.9 (4)
C18A—C19A—H19A	122.7	C14—C13—C11	122.5 (4)
C19A—C20A—S4A	109.2 (6)	C15—C14—C13	113.1 (4)
C19A—C20A—H20A	125.4	C15—C14—H14A	123.5
S4A—C20A—H20A	125.4	C13—C14—H14A	123.5
S4B—C20B—H20B	125.6	C14—C15—S3	109.6 (3)
O1—C1—C3A	122.0 (4)	C14—C15—H15A	125.2
O1—C1—C6	118.5 (4)	S3—C15—H15A	125.2
C3A—C1—C6	119.5 (3)	O4—C16—C18A	110.4 (3)
O2—C6—C8	109.6 (3)	O4—C16—C11	109.8 (3)
O2—C6—C1	109.3 (3)	C18A—C16—C11	109.3 (3)
C8—C6—C1	110.4 (3)	O4—C16—H16A	109.1
O2—C6—H6A	109.1	C18A—C16—H16A	109.1
C8—C6—H6A	109.1	C11—C16—H16A	109.1
C1—C6—H6A	109.1	C16—O4—H4A	109.5