Nona­decane-1,19-di­thiol

The title compound, C₁₉H₄₀S₂, has mercapto groups at both ends of the molecular skeleton, which has an all-trans conformation. The mol­ecules form layers and the long axes of the mol­ecules are inclined with respect to the layers in the crystal structure. This molecular arrangement is similar to that of the smectic C phase of liquid crystals.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.061
• wR factor = 0.127
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         48 Perc.
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.68 mm
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.23
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT420_ALERT_2_C D-H Without Acceptor       S1     -   H1S    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       S2     -   H2S    ...          ?

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   7 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
   4 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: CrystalStructure (Molecular Structure Corporation & Rigaku Corporation, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

(I)

Crystal data

C19H40S2	Z = 2
Mr = 332.65	F(000) = 372.00
Triclinic, P1	Dx = 1.044 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.5418 Å
a = 4.7557 (6) Å	Cell parameters from 24 reflections
b = 5.5781 (13) Å	θ = 9.4–18.2°
c = 40.930 (4) Å	µ = 2.21 mm^−1
α = 92.452 (12)°	T = 296 K
β = 92.094 (9)°	Plate, colorless
γ = 102.365 (13)°	0.68 × 0.15 × 0.01 mm
V = 1058.5 (3) Å^3

Data collection

Rigaku AFC-5R diffractometer	Rint = 0.024
ω scans	θmax = 70.1°
Absorption correction: ψ scan (North et al., 1968)	h = −5→5
Tmin = 0.748, Tmax = 0.977	k = −1→6
5132 measured reflections	l = −49→49
3825 independent reflections	3 standard reflections every 150 reflections
1834 reflections with F^2 > 2σ(F^2)	intensity decay: 21.5%

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.061	w = (4Fo^2)/[0.0001Fo^2 + 7.6σ^2(Fo) + 0.19]
wR(F^2) = 0.127	(Δ/σ)max = 0.001
S = 1.00	Δρmax = 0.41 e Å^−3
3822 reflections	Δρmin = −0.50 e Å^−3
234 parameters

Special details

Refinement. Refinement using reflections with F² > -3.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.8556 (3)	2.2560 (2)	0.97088 (3)	0.1035 (5)
S2	−0.1540 (3)	−1.2955 (2)	0.52554 (3)	0.1083 (6)
C1	0.6027 (8)	2.0035 (7)	0.95041 (9)	0.080 (1)
C2	0.7286 (7)	1.8638 (6)	0.92474 (8)	0.060 (1)
C3	0.5064 (7)	1.6614 (6)	0.90662 (8)	0.060 (1)
C4	0.6295 (7)	1.5158 (6)	0.88084 (8)	0.057 (1)
C5	0.4066 (7)	1.3171 (6)	0.86228 (8)	0.056 (1)
C6	0.5284 (7)	1.1691 (6)	0.83675 (8)	0.055 (1)
C7	0.3041 (7)	0.9706 (6)	0.81806 (8)	0.055 (1)
C8	0.4253 (7)	0.8217 (6)	0.79258 (8)	0.054 (1)
C9	0.2010 (7)	0.6247 (6)	0.77388 (8)	0.054 (1)
C10	0.3220 (7)	0.4740 (6)	0.74841 (8)	0.054 (1)
C11	0.0974 (7)	0.2777 (6)	0.72965 (8)	0.055 (1)
C12	0.2190 (7)	0.1271 (6)	0.70433 (8)	0.055 (1)
C13	−0.0056 (7)	−0.0686 (6)	0.68545 (8)	0.056 (1)
C14	0.1169 (7)	−0.2198 (6)	0.66022 (8)	0.056 (1)
C15	−0.1073 (7)	−0.4145 (6)	0.64112 (8)	0.058 (1)
C16	0.0160 (7)	−0.5647 (6)	0.61593 (8)	0.059 (1)
C17	−0.2083 (7)	−0.7566 (6)	0.59632 (8)	0.063 (1)
C18	−0.0813 (8)	−0.9109 (6)	0.57211 (8)	0.065 (1)
C19	−0.3063 (8)	−1.0945 (7)	0.55166 (9)	0.085 (2)
H1	0.5186	1.8922	0.96605	0.093*
H2	0.4570	2.0688	0.93977	0.093*
H3	0.8191	1.9748	0.90939	0.070*
H4	0.8684	1.7912	0.93531	0.070*
H5	0.4142	1.5525	0.92211	0.070*
H6	0.3682	1.7349	0.89590	0.071*
H7	0.7249	1.6253	0.86561	0.067*
H8	0.7649	1.4397	0.89162	0.067*
H9	0.3115	1.2076	0.87754	0.066*
H10	0.2710	1.3935	0.85157	0.066*
H11	0.6241	1.2785	0.82151	0.064*
H12	0.6634	1.0920	0.84744	0.064*
H13	0.2078	0.8619	0.83335	0.064*
H14	0.1697	1.0480	0.80731	0.065*
H15	0.5223	0.9304	0.77736	0.063*
H16	0.5591	0.7438	0.80335	0.063*
H17	0.1031	0.5166	0.78912	0.064*
H18	0.0680	0.7027	0.76298	0.064*
H19	0.4202	0.5819	0.73317	0.064*
H20	0.4547	0.3955	0.75930	0.064*
H21	−0.0008	0.1695	0.74486	0.065*
H22	−0.0355	0.3560	0.71876	0.065*
H23	0.3186	0.2356	0.68924	0.065*
H24	0.3506	0.0479	0.71526	0.065*
H25	−0.1060	−0.1765	0.70055	0.066*
H26	−0.1366	0.0107	0.67441	0.066*
H27	0.2182	−0.1118	0.64520	0.067*
H28	0.2470	−0.2999	0.67128	0.067*
H29	−0.2092	−0.5225	0.65611	0.069*
H30	−0.2371	−0.3347	0.62995	0.069*
H31	0.1206	−0.4563	0.60116	0.069*
H32	0.1434	−0.6466	0.62714	0.069*
H33	−0.3173	−0.8620	0.61108	0.074*
H34	−0.3320	−0.6749	0.58444	0.074*
H35	0.0339	−0.8053	0.55786	0.078*
H36	0.0361	−0.9984	0.58397	0.078*
H37	−0.4155	−1.0063	0.53877	0.099*
H38	−0.4289	−1.1923	0.56608	0.099*
H2s	−0.193 (8)	−1.192 (7)	0.504 (1)	0.1299*
H1s	0.896 (9)	2.156 (7)	0.986 (1)	0.1241*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.130 (1)	0.082 (1)	0.086 (1)	0.0026 (9)	−0.0106 (9)	−0.0310 (7)
S2	0.140 (1)	0.094 (1)	0.0883 (9)	0.0298 (9)	0.0016 (9)	−0.0404 (8)
C1	0.084 (3)	0.075 (3)	0.074 (3)	0.008 (2)	0.007 (2)	−0.033 (2)
C2	0.063 (3)	0.054 (2)	0.057 (2)	0.006 (2)	0.001 (2)	−0.013 (2)
C3	0.058 (3)	0.057 (2)	0.061 (2)	0.006 (2)	0.005 (2)	−0.018 (2)
C4	0.055 (3)	0.055 (2)	0.057 (2)	0.005 (2)	0.003 (2)	−0.016 (2)
C5	0.052 (3)	0.056 (2)	0.058 (2)	0.006 (2)	0.007 (2)	−0.014 (2)
C6	0.053 (3)	0.053 (2)	0.055 (2)	0.006 (2)	0.004 (2)	−0.015 (2)
C7	0.052 (3)	0.055 (2)	0.054 (2)	0.006 (2)	0.004 (2)	−0.014 (2)
C8	0.052 (2)	0.051 (2)	0.055 (2)	0.006 (2)	0.003 (2)	−0.016 (2)
C9	0.052 (3)	0.054 (2)	0.053 (2)	0.006 (2)	0.003 (2)	−0.014 (2)
C10	0.054 (2)	0.051 (2)	0.055 (2)	0.007 (2)	0.004 (2)	−0.017 (2)
C11	0.054 (3)	0.054 (2)	0.055 (2)	0.007 (2)	0.004 (2)	−0.015 (2)
C12	0.054 (3)	0.053 (2)	0.055 (2)	0.008 (2)	0.006 (2)	−0.015 (2)
C13	0.055 (3)	0.056 (2)	0.055 (2)	0.007 (2)	0.005 (2)	−0.015 (2)
C14	0.055 (3)	0.058 (2)	0.053 (2)	0.010 (2)	0.005 (2)	−0.016 (2)
C15	0.059 (3)	0.057 (2)	0.055 (2)	0.008 (2)	0.003 (2)	−0.017 (2)
C16	0.058 (3)	0.058 (2)	0.057 (2)	0.009 (2)	0.003 (2)	−0.016 (2)
C17	0.060 (3)	0.063 (3)	0.061 (2)	0.006 (2)	0.003 (2)	−0.022 (2)
C18	0.068 (3)	0.068 (3)	0.059 (2)	0.016 (2)	0.001 (2)	−0.020 (2)
C19	0.077 (3)	0.090 (3)	0.081 (3)	0.012 (3)	−0.005 (2)	−0.041 (3)

Geometric parameters (Å, º)

S1—C1	1.798 (3)	C5—H9	0.95
S2—C19	1.796 (3)	C5—H10	0.95
C1—C2	1.498 (4)	C6—H11	0.95
C2—C3	1.517 (4)	C6—H12	0.95
C3—C4	1.514 (4)	C7—H13	0.95
C4—C5	1.515 (4)	C7—H14	0.95
C5—C6	1.511 (4)	C8—H15	0.95
C6—C7	1.520 (4)	C8—H16	0.95
C7—C8	1.512 (4)	C9—H17	0.95
C8—C9	1.516 (4)	C9—H18	0.95
C9—C10	1.517 (4)	C10—H19	0.95
C10—C11	1.516 (4)	C10—H20	0.95
C11—C12	1.514 (4)	C11—H21	0.95
C12—C13	1.516 (4)	C11—H22	0.95
C13—C14	1.516 (4)	C12—H23	0.95
C14—C15	1.516 (4)	C12—H24	0.95
C15—C16	1.513 (4)	C13—H25	0.95
C16—C17	1.517 (4)	C13—H26	0.95
C17—C18	1.511 (4)	C14—H27	0.95
C18—C19	1.512 (4)	C14—H28	0.95
S1—H1s	0.90 (3)	C15—H29	0.95
S2—H2s	1.10 (4)	C15—H30	0.95
C1—H1	0.95	C16—H31	0.95
C1—H2	0.95	C16—H32	0.95
C2—H3	0.95	C17—H33	0.95
C2—H4	0.95	C17—H34	0.95
C3—H5	0.95	C18—H35	0.95
C3—H6	0.95	C18—H36	0.95
C4—H7	0.95	C19—H37	0.95
C4—H8	0.95	C19—H38	0.95
S1^i···S1^ii	3.5474 (18)	S2···S2^iii	3.6011 (19)
S1—C1—C2	114.6 (3)	C9—C8—H16	108.1
C1—C2—C3	113.2 (3)	H15—C8—H16	109.5
C2—C3—C4	114.1 (3)	C8—C9—H17	108.4
C3—C4—C5	114.1 (3)	C10—C9—H17	108.5
C4—C5—C6	114.3 (3)	C8—C9—H18	108.1
C5—C6—C7	114.2 (3)	C10—C9—H18	107.9
C6—C7—C8	114.4 (3)	H17—C9—H18	109.5
C7—C8—C9	114.2 (3)	C9—C10—H19	108.5
C8—C9—C10	114.4 (3)	C11—C10—H19	108.3
C9—C10—C11	114.3 (3)	C9—C10—H20	108.0
C10—C11—C12	114.2 (3)	C11—C10—H20	108.1
C11—C12—C13	114.2 (3)	H19—C10—H20	109.5
C12—C13—C14	114.1 (3)	C10—C11—H21	108.4
C13—C14—C15	114.3 (3)	C12—C11—H21	108.3
C14—C15—C16	114.1 (3)	C10—C11—H22	108.2
C15—C16—C17	114.2 (3)	C12—C11—H22	108.2
C16—C17—C18	113.6 (3)	H21—C11—H22	109.5
C17—C18—C19	113.4 (3)	C11—C12—H23	108.3
S2—C19—C18	113.1 (3)	C13—C12—H23	108.6
C1—S1—H1s	90 (3)	C11—C12—H24	108.2
C19—S2—H2s	91 (2)	C13—C12—H24	108.0
S1—C1—H1	109.5	H23—C12—H24	109.5
C2—C1—H1	108.5	C12—C13—H25	108.6
S1—C1—H2	107.6	C14—C13—H25	108.4
C2—C1—H2	107.1	C12—C13—H26	108.0
H1—C1—H2	109.4	C14—C13—H26	108.1
C1—C2—H3	109.1	H25—C13—H26	109.5
C3—C2—H3	108.9	C13—C14—H27	108.4
C1—C2—H4	107.7	C15—C14—H27	108.5
C3—C2—H4	108.4	C13—C14—H28	108.1
H3—C2—H4	109.5	C15—C14—H28	108.0
C2—C3—H5	108.6	H27—C14—H28	109.5
C4—C3—H5	109.0	C14—C15—H29	108.6
C2—C3—H6	108.1	C16—C15—H29	108.7
C4—C3—H6	107.5	C14—C15—H30	108.1
H5—C3—H6	109.5	C16—C15—H30	107.8
C3—C4—H7	108.9	H29—C15—H30	109.5
C5—C4—H7	108.6	C15—C16—H31	108.6
C3—C4—H8	107.5	C17—C16—H31	108.4
C5—C4—H8	108.2	C15—C16—H32	107.8
H7—C4—H8	109.5	C17—C16—H32	108.2
C4—C5—H9	108.5	H31—C16—H32	109.5
C6—C5—H9	108.3	C16—C17—H33	108.6
C4—C5—H10	108.1	C18—C17—H33	108.7
C6—C5—H10	108.1	C16—C17—H34	108.5
H9—C5—H10	109.5	C18—C17—H34	107.9
C5—C6—H11	108.4	H33—C17—H34	109.5
C7—C6—H11	108.5	C17—C18—H35	108.8
C5—C6—H12	108.2	C19—C18—H35	108.5
C7—C6—H12	108.0	C17—C18—H36	108.2
H11—C6—H12	109.5	C19—C18—H36	108.4
C6—C7—H13	108.4	H35—C18—H36	109.4
C8—C7—H13	108.5	S2—C19—H37	109.7
C6—C7—H14	108.0	C18—C19—H37	108.3
C8—C7—H14	108.1	S2—C19—H38	108.2
H13—C7—H14	109.5	C18—C19—H38	108.1
C7—C8—H15	108.4	H37—C19—H38	109.5
C9—C8—H15	108.4	S1^i—H1s^i—S1^ii	80 (2)
C7—C8—H16	108.1	S2—H2s—S2^iii	72.7 (19)
S1—C1—C2—C3	−176.7 (2)	C10—C11—C12—C13	−179.8 (3)
C1—C2—C3—C4	−179.3 (3)	C11—C12—C13—C14	−179.7 (3)
C2—C3—C4—C5	−178.8 (3)	C12—C13—C14—C15	−179.6 (3)
C3—C4—C5—C6	−179.4 (3)	C13—C14—C15—C16	179.9 (3)
C4—C5—C6—C7	−179.7 (3)	C14—C15—C16—C17	−178.9 (3)
C5—C6—C7—C8	−179.8 (3)	C15—C16—C17—C18	−178.0 (3)
C6—C7—C8—C9	−179.7 (3)	C16—C17—C18—C19	−177.6 (3)
C7—C8—C9—C10	−179.7 (3)	C17—C18—C19—S2	−174.8 (2)
C8—C9—C10—C11	−179.8 (3)	C2—C1—S1—H1s	−90 (3)
C9—C10—C11—C12	−179.8 (3)	C18—C19—S2—H2s	−104 (2)

Symmetry codes: (i) x−1, y−1, z−1; (ii) −x+1, −y+4, −z+1; (iii) −x, −y−3, −z+1.