Do­decyl 2-nitro­phenyl disulphide

Do­decyl 2-nitro­phenyl disulphide, C₁₈H₂₉NO₂S₂, contains an intramolecular S...O contact of 2.623 (3) Å. The angle between the planes of the NO₂ group and the attached phenyl ring is 4.2 (3)°. The thermal vibrations of the atoms increase along the paraffinic chain. The nitro­so O atom not involved in the S...O intramolecular contact also has high thermal motion. Attempts to create disordered models to allow for the thermal motions were unsuccessful.

S1. Comment

Examination of the title structure, (I), with PLATON (Spek, 1999) showed that there were no solvent-accessible voids in the crystal lattice.

S2. Experimental

Dodecyl 2-nitrophenyl disulfide was obtained from Bu₃SC₁₂H₂₅ and 2-O₂NC₆H₄SCl in CHCl₃ at room temperature. The solution was filtered, the filtrate was chromatographed on silica gel and the the product was recrystallized from ethanol, m.p. 314–316 K.

S3. Refinement

Molecule (I) crystallized in the monoclinic system; space group P2₁/c from the systematic absences. H atoms were treated as riding atoms with C—H 0.92–0.99 Å. An attempt to refine atoms O22 and C17 as disordered atoms, on two sites as indicated by SHELXL, with the site occupancies for each atom pair tied by a free-variable resulted in a higher R factor. The high thermal motion of the atoms is not unexpected since this compound has a very low melting point.

Computing details

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Dodecyl 2-nitrophenyl disulfide

Crystal data

C18H29NO2S2	F(000) = 768
Mr = 355.54	Dx = 1.175 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 34.497 (7) Å	Cell parameters from 3701 reflections
b = 7.796 (2) Å	θ = 2.4–26.0°
c = 7.503 (2) Å	µ = 0.27 mm^−1
β = 95.12 (3)°	T = 150 K
V = 2009.8 (8) Å^3	Plate, yellow
Z = 4	0.2 × 0.1 × 0.1 mm

Data collection

KappaCCD diffractometer	3701 independent reflections
Radiation source: fine-focus sealed X-ray tube	2053 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.081
ϕ scans and ω scans with κ offsets	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan SORTAV (Blessing, 1995, 1997)	h = −42→42
Tmin = 0.947, Tmax = 0.973	k = −9→9
17677 measured reflections	l = −9→9

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.210	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.1121P)^2 + 0.0783P] where P = (Fo^2 + 2Fc^2)/3
3701 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.80 e Å^−3
0 restraints	Δρmin = −0.34 e Å^−3

Special details

Experimental. KappaCCD diffractometer using the following programs. Collect: Data collection software (Hooft, 1998) [Hooft, R. (1998). Nonius BV, Delft, The Netherlands] is a graphical user interface written by Enraf–Nonius which encompasses the following programs. DENZO (Otwinowski & Minor, 1997) and indexing and data collection software package and a scaling package, SCALEPACK both of which programs are produced by the company HKL. Absorption corrections are performed by the SORTAV package (Blessing, 1995, 1997). High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file. Low-temperature data is collected using an Oxford Cryosystems Cryostream cooler (Cosier & Glazer, 1986) [Cosier, J. & Glazer, A·M. (1986). J. Appl. Cryst. 19, 105–107]. The R_int and final R values are high since high order data are very weak and data collection at High theta values was difficult.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.35213 (3)	0.25025 (12)	0.36073 (13)	0.0399 (4)
S2	0.33501 (3)	0.49561 (14)	0.29997 (15)	0.0486 (4)
C1	0.40041 (11)	0.2693 (5)	0.4629 (5)	0.0329 (9)
C2	0.42386 (11)	0.1282 (4)	0.5119 (5)	0.0337 (9)
N2	0.41001 (11)	−0.0454 (4)	0.4774 (5)	0.0471 (10)
O21	0.37634 (9)	−0.0662 (3)	0.4133 (4)	0.0487 (8)
O22	0.43224 (10)	−0.1645 (4)	0.5108 (6)	0.0956 (14)
C3	0.46132 (12)	0.1437 (5)	0.5930 (5)	0.0378 (10)
C4	0.47690 (11)	0.3013 (5)	0.6288 (5)	0.0386 (10)
C5	0.45451 (12)	0.4459 (5)	0.5844 (5)	0.0390 (10)
C6	0.41702 (11)	0.4310 (5)	0.5021 (5)	0.0363 (10)
C7	0.31782 (12)	0.5715 (5)	0.5102 (5)	0.0499 (12)
C8	0.28194 (12)	0.4854 (5)	0.5614 (6)	0.0484 (12)
C9	0.26980 (12)	0.5515 (6)	0.7359 (6)	0.0546 (13)
C10	0.23242 (13)	0.4705 (6)	0.7960 (6)	0.0621 (14)
C11	0.22145 (14)	0.5338 (6)	0.9766 (6)	0.0631 (14)
C12	0.18329 (14)	0.4626 (7)	1.0310 (7)	0.0707 (15)
C13	0.17285 (14)	0.5258 (7)	1.2155 (7)	0.0725 (16)
C14	0.13423 (16)	0.4617 (8)	1.2636 (7)	0.0862 (18)
C15	0.12373 (16)	0.5269 (8)	1.4497 (7)	0.0924 (19)
C16	0.08466 (17)	0.4673 (10)	1.4975 (8)	0.113 (2)
C17	0.0747 (2)	0.5385 (12)	1.6870 (9)	0.146 (3)
C18	0.0356 (2)	0.4906 (17)	1.7686 (14)	0.252 (7)
H3	0.4762	0.0438	0.6237	0.045*
H4	0.5027	0.3125	0.6833	0.046*
H5	0.4650	0.5566	0.6108	0.047*
H6	0.4024	0.5317	0.4719	0.044*
H7A	0.3388	0.5543	0.6075	0.060*
H7B	0.3128	0.6963	0.5001	0.060*
H8A	0.2866	0.3603	0.5712	0.058*
H8B	0.2606	0.5044	0.4663	0.058*
H9A	0.2659	0.6771	0.7257	0.066*
H9B	0.2913	0.5311	0.8301	0.066*
H10A	0.2107	0.4952	0.7045	0.075*
H10B	0.2358	0.3445	0.8018	0.075*
H11A	0.2425	0.5025	1.0693	0.076*
H11B	0.2197	0.6605	0.9733	0.076*
H12A	0.1848	0.3358	1.0329	0.085*
H12B	0.1621	0.4955	0.9396	0.085*
H13A	0.1933	0.4877	1.3080	0.087*
H13B	0.1726	0.6528	1.2158	0.087*
H14A	0.1345	0.3347	1.2641	0.103*
H14B	0.1138	0.4993	1.1708	0.103*
H15A	0.1439	0.4868	1.5426	0.111*
H15B	0.1242	0.6538	1.4501	0.111*
H16A	0.0842	0.3403	1.4997	0.136*
H16B	0.0644	0.5061	1.4044	0.136*
H17A	0.0962	0.5029	1.7753	0.175*
H17B	0.0756	0.6652	1.6802	0.175*
H18A	0.0207	0.5952	1.7862	0.377*	0.50
H18B	0.0415	0.4330	1.8839	0.377*	0.50
H18C	0.0203	0.4136	1.6865	0.377*	0.50
H18D	0.0343	0.3660	1.7849	0.377*	0.50
H18E	0.0134	0.5282	1.6871	0.377*	0.50
H18F	0.0347	0.5476	1.8846	0.377*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0477 (6)	0.0291 (6)	0.0400 (7)	−0.0020 (5)	−0.0113 (5)	−0.0014 (5)
S2	0.0605 (8)	0.0365 (7)	0.0447 (7)	0.0062 (5)	−0.0182 (5)	0.0062 (5)
C1	0.048 (2)	0.025 (2)	0.024 (2)	−0.0025 (18)	−0.0062 (17)	−0.0002 (17)
C2	0.046 (2)	0.019 (2)	0.035 (2)	0.0015 (17)	−0.0013 (19)	−0.0005 (17)
N2	0.055 (2)	0.024 (2)	0.060 (3)	−0.0038 (18)	−0.007 (2)	0.0025 (17)
O21	0.059 (2)	0.0295 (17)	0.055 (2)	−0.0078 (14)	−0.0092 (16)	−0.0057 (14)
O22	0.079 (2)	0.0201 (19)	0.178 (4)	0.0082 (18)	−0.043 (2)	0.000 (2)
C3	0.052 (3)	0.025 (2)	0.035 (2)	0.0060 (19)	−0.0053 (19)	0.0023 (18)
C4	0.044 (2)	0.032 (2)	0.037 (2)	0.0003 (19)	−0.0093 (19)	0.0023 (19)
C5	0.054 (3)	0.028 (2)	0.035 (2)	−0.0064 (19)	0.000 (2)	−0.0051 (18)
C6	0.047 (2)	0.025 (2)	0.035 (2)	0.0020 (18)	−0.0038 (19)	0.0021 (18)
C7	0.060 (3)	0.029 (2)	0.056 (3)	0.012 (2)	−0.021 (2)	−0.009 (2)
C8	0.049 (3)	0.040 (3)	0.053 (3)	0.009 (2)	−0.015 (2)	−0.009 (2)
C9	0.047 (3)	0.044 (3)	0.069 (3)	0.007 (2)	−0.018 (2)	−0.009 (2)
C10	0.051 (3)	0.056 (3)	0.075 (4)	0.007 (2)	−0.015 (3)	−0.010 (3)
C11	0.054 (3)	0.071 (4)	0.061 (3)	0.008 (3)	−0.015 (2)	−0.014 (3)
C12	0.050 (3)	0.082 (4)	0.077 (4)	0.007 (3)	−0.011 (3)	−0.002 (3)
C13	0.051 (3)	0.099 (4)	0.065 (4)	0.006 (3)	−0.008 (3)	−0.010 (3)
C14	0.060 (4)	0.114 (5)	0.081 (4)	0.007 (3)	−0.010 (3)	−0.004 (4)
C15	0.058 (4)	0.137 (6)	0.079 (4)	0.006 (4)	−0.011 (3)	0.000 (4)
C16	0.060 (4)	0.182 (7)	0.096 (5)	0.006 (4)	−0.003 (4)	0.022 (5)
C17	0.076 (5)	0.265 (11)	0.097 (6)	−0.005 (6)	0.010 (4)	0.015 (6)
C18	0.073 (6)	0.387 (19)	0.288 (15)	−0.007 (8)	−0.024 (8)	0.109 (12)

Geometric parameters (Å, º)

S1—C1	1.776 (4)	C7—C8	1.488 (6)
S1—S2	2.0414 (15)	C8—C9	1.501 (6)
S2—C7	1.832 (4)	C9—C10	1.539 (6)
C1—C2	1.395 (5)	C10—C11	1.521 (6)
C1—C6	1.405 (5)	C11—C12	1.518 (7)
C2—C3	1.384 (5)	C12—C13	1.542 (6)
C2—N2	1.450 (5)	C13—C14	1.497 (7)
N2—O22	1.216 (4)	C14—C15	1.559 (7)
N2—O21	1.228 (4)	C15—C16	1.499 (8)
C3—C4	1.358 (5)	C16—C17	1.593 (8)
C4—C5	1.390 (5)	C17—C18	1.574 (10)
C5—C6	1.387 (5)
C1—S1—S2	105.03 (13)	C6—C5—C4	121.0 (4)
C7—S2—S1	102.69 (14)	C5—C6—C1	121.0 (3)
C2—C1—C6	115.9 (3)	C8—C7—S2	114.6 (3)
C2—C1—S1	123.2 (3)	C7—C8—C9	111.9 (3)
C6—C1—S1	121.0 (3)	C8—C9—C10	114.9 (4)
C3—C2—C1	122.9 (3)	C11—C10—C9	114.2 (4)
C3—C2—N2	116.1 (3)	C12—C11—C10	114.3 (4)
C1—C2—N2	121.0 (3)	C11—C12—C13	113.7 (4)
O22—N2—O21	122.5 (3)	C14—C13—C12	113.2 (4)
O22—N2—C2	119.0 (3)	C13—C14—C15	113.0 (5)
O21—N2—C2	118.6 (3)	C16—C15—C14	113.5 (5)
C4—C3—C2	120.3 (3)	C15—C16—C17	112.1 (6)
C3—C4—C5	119.0 (4)	C18—C17—C16	121.7 (8)
C1—S1—S2—C7	−84.38 (19)	C4—C5—C6—C1	0.7 (6)
S2—S1—C1—C2	−174.8 (3)	C2—C1—C6—C5	0.1 (6)
S2—S1—C1—C6	6.4 (3)	S1—C1—C6—C5	179.0 (3)
C6—C1—C2—C3	−0.5 (6)	S1—S2—C7—C8	−67.4 (3)
S1—C1—C2—C3	−179.4 (3)	S2—C7—C8—C9	179.1 (3)
C6—C1—C2—N2	−179.7 (3)	C7—C8—C9—C10	179.0 (4)
S1—C1—C2—N2	1.4 (5)	C8—C9—C10—C11	177.7 (4)
C3—C2—N2—O22	−4.3 (6)	C9—C10—C11—C12	176.4 (4)
C1—C2—N2—O22	175.0 (4)	C10—C11—C12—C13	179.2 (4)
C3—C2—N2—O21	176.7 (4)	C11—C12—C13—C14	177.1 (4)
C1—C2—N2—O21	−4.1 (6)	C12—C13—C14—C15	−179.7 (4)
C1—C2—C3—C4	0.1 (6)	C13—C14—C15—C16	178.5 (5)
N2—C2—C3—C4	179.3 (3)	C14—C15—C16—C17	−179.2 (5)
C2—C3—C4—C5	0.6 (6)	C15—C16—C17—C18	−178.7 (7)
C3—C4—C5—C6	−1.0 (6)