Meth­yl 2-(cyclo­hexyl­amino)cyclo­pent-1-ene-1-dithio­carboxyl­ate

In the title mol­ecule, C₁₃H₂₁NS₂, the Csp²—S and C=S bond lengths are 1.770 (3) and 1.685 (3) Å, respectively. An inter­molecular N—H...S hydrogen bond defines the preferred conformation of the mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.044
• wR factor = 0.112
• Data-to-parameter ratio = 20.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         45 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.85 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C7      ..       5.20 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C10
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C12
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C8
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART-NT (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus and XPREP (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

C13H21NS2	F(000) = 552
Mr = 255.43	Dx = 1.224 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 816 reflections
a = 19.9786 (17) Å	θ = 2.3–24.2°
b = 5.3550 (4) Å	µ = 0.36 mm^−1
c = 13.5855 (12) Å	T = 293 K
β = 107.507 (2)°	Plate, yellow
V = 1386.1 (2) Å^3	0.12 × 0.09 × 0.04 mm
Z = 4

Data collection

Bruker SMART CCD 1K diffractometer	1362 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.099
ω scans	θmax = 27°, θmin = 1.1°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −25→25
Tmin = 0.958, Tmax = 0.986	k = −6→6
11770 measured reflections	l = −17→17
3025 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.044	w = 1/[σ^2(Fo^2) + (0.0476P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.112	(Δ/σ)max = 0.001
S = 0.83	Δρmax = 0.18 e Å^−3
3025 reflections	Δρmin = −0.18 e Å^−3
150 parameters

Special details

Experimental. The intensity data was collected on a Bruker SMART CCD 1 K diffractometer using an exposure time of 25 s/frame. A total of 1650 frames were collected with a frame width of 0.3° covering up to θ = 27.0° with 100% completeness accomplished. The first 50 frames were recollected at the end of each data collection to check for decay; none was found.

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.

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

	x	y	z	Uiso*/Ueq
S1	0.41452 (4)	0.33778 (15)	0.24081 (6)	0.0523 (3)
S2	0.25853 (4)	0.31658 (16)	0.20017 (6)	0.0626 (3)
N1	0.23173 (12)	0.6933 (5)	0.35005 (19)	0.0477 (6)
C1	0.38711 (15)	0.0860 (5)	0.1517 (2)	0.0599 (9)
H1A	0.361	−0.0326	0.1784	0.09*
H1B	0.4276	0.0057	0.1418	0.09*
H1C	0.358	0.1493	0.0868	0.09*
C2	0.33689 (13)	0.4396 (5)	0.2656 (2)	0.0422 (7)
C3	0.34984 (12)	0.6235 (5)	0.34186 (19)	0.0372 (7)
C4	0.42137 (13)	0.7247 (5)	0.3983 (2)	0.0455 (7)
H4A	0.4433	0.7959	0.3499	0.055*
H4B	0.4513	0.5931	0.4368	0.055*
C5	0.40990 (14)	0.9257 (5)	0.4713 (2)	0.0528 (8)
H5A	0.4372	0.8885	0.5419	0.063*
H5B	0.4242	1.0877	0.4528	0.063*
C6	0.33212 (12)	0.9267 (5)	0.46115 (19)	0.0442 (7)
H6A	0.3245	0.881	0.526	0.053*
H6B	0.3121	1.0908	0.441	0.053*
C7	0.29978 (14)	0.7387 (5)	0.37969 (19)	0.0394 (7)
C8	0.18007 (13)	0.7888 (5)	0.3966 (2)	0.0470 (7)
H8	0.1981	0.9441	0.4332	0.056*
C9	0.16873 (17)	0.6045 (7)	0.4729 (3)	0.0833 (12)
H9A	0.2121	0.5845	0.5285	0.1*
H9B	0.1567	0.4439	0.4392	0.1*
C10	0.1111 (2)	0.6838 (8)	0.5176 (3)	0.1061 (14)
H10A	0.1036	0.5532	0.5627	0.127*
H10B	0.1256	0.8336	0.5587	0.127*
C11	0.04421 (18)	0.7333 (7)	0.4348 (3)	0.0807 (11)
H11A	0.0268	0.579	0.3987	0.097*
H11B	0.0093	0.7943	0.4655	0.097*
C12	0.05494 (18)	0.9208 (8)	0.3604 (3)	0.0944 (13)
H12A	0.0669	1.0802	0.3952	0.113*
H12B	0.0114	0.9419	0.305	0.113*
C13	0.11287 (16)	0.8451 (7)	0.3146 (3)	0.0756 (10)
H13A	0.098	0.6987	0.2714	0.091*
H13B	0.1206	0.9793	0.2713	0.091*
H1	0.2170 (14)	0.578 (5)	0.297 (2)	0.067 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0507 (5)	0.0586 (5)	0.0517 (5)	0.0051 (4)	0.0214 (4)	−0.0040 (4)
S2	0.0504 (5)	0.0741 (6)	0.0619 (5)	−0.0098 (4)	0.0146 (4)	−0.0258 (5)
N1	0.0378 (14)	0.0601 (17)	0.0485 (15)	−0.0052 (13)	0.0179 (12)	−0.0128 (14)
C1	0.076 (2)	0.053 (2)	0.056 (2)	0.0106 (16)	0.0275 (17)	−0.0027 (15)
C2	0.0446 (17)	0.0442 (17)	0.0401 (16)	−0.0008 (13)	0.0160 (13)	0.0076 (14)
C3	0.0338 (15)	0.0425 (18)	0.0365 (15)	0.0000 (12)	0.0124 (12)	0.0022 (13)
C4	0.0393 (15)	0.0501 (18)	0.0461 (16)	−0.0009 (13)	0.0112 (13)	0.0005 (15)
C5	0.0514 (19)	0.059 (2)	0.0471 (18)	−0.0121 (15)	0.0140 (15)	−0.0069 (16)
C6	0.0460 (18)	0.0475 (18)	0.0398 (17)	−0.0075 (13)	0.0140 (14)	−0.0060 (13)
C7	0.0410 (16)	0.0432 (17)	0.0332 (14)	−0.0060 (13)	0.0100 (12)	0.0022 (13)
C8	0.0429 (17)	0.0526 (19)	0.0497 (17)	−0.0031 (14)	0.0203 (14)	−0.0083 (15)
C9	0.066 (2)	0.118 (3)	0.072 (2)	0.022 (2)	0.029 (2)	0.038 (2)
C10	0.093 (3)	0.172 (4)	0.072 (3)	−0.008 (3)	0.053 (2)	0.009 (3)
C11	0.066 (2)	0.093 (3)	0.099 (3)	−0.009 (2)	0.049 (2)	−0.014 (2)
C12	0.062 (2)	0.105 (3)	0.127 (4)	0.032 (2)	0.045 (2)	0.014 (3)
C13	0.055 (2)	0.102 (3)	0.076 (2)	0.022 (2)	0.0295 (18)	0.029 (2)

Geometric parameters (Å, º)

S1—C2	1.770 (3)	C6—H6A	0.97
S1—C1	1.785 (3)	C6—H6B	0.97
S2—C2	1.685 (3)	C8—C13	1.495 (4)
N1—C7	1.319 (3)	C8—C9	1.496 (4)
N1—C8	1.456 (3)	C8—H8	0.98
N1—H1	0.93 (3)	C9—C10	1.515 (4)
C1—H1A	0.96	C9—H9A	0.97
C1—H1B	0.96	C9—H9B	0.97
C1—H1C	0.96	C10—C11	1.489 (4)
C2—C3	1.396 (3)	C10—H10A	0.97
C3—C7	1.398 (3)	C10—H10B	0.97
C3—C4	1.505 (3)	C11—C12	1.486 (5)
C4—C5	1.528 (3)	C11—H11A	0.97
C4—H4A	0.97	C11—H11B	0.97
C4—H4B	0.97	C12—C13	1.525 (4)
C5—C6	1.518 (3)	C12—H12A	0.97
C5—H5A	0.97	C12—H12B	0.97
C5—H5B	0.97	C13—H13A	0.97
C6—C7	1.492 (3)	C13—H13B	0.97
C2—S1—C1	104.74 (13)	N1—C8—C13	110.0 (2)
C7—N1—C8	127.1 (2)	N1—C8—C9	110.1 (2)
C7—N1—H1	114.6 (17)	C13—C8—C9	111.1 (2)
C8—N1—H1	118.2 (17)	N1—C8—H8	108.5
S1—C1—H1A	109.5	C13—C8—H8	108.5
S1—C1—H1B	109.5	C9—C8—H8	108.5
H1A—C1—H1B	109.5	C8—C9—C10	112.6 (3)
S1—C1—H1C	109.5	C8—C9—H9A	109.1
H1A—C1—H1C	109.5	C10—C9—H9A	109.1
H1B—C1—H1C	109.5	C8—C9—H9B	109.1
C3—C2—S2	127.1 (2)	C10—C9—H9B	109.1
C3—C2—S1	112.41 (19)	H9A—C9—H9B	107.8
S2—C2—S1	120.49 (17)	C11—C10—C9	111.4 (3)
C2—C3—C7	126.2 (2)	C11—C10—H10A	109.4
C2—C3—C4	124.6 (2)	C9—C10—H10A	109.4
C7—C3—C4	109.2 (2)	C11—C10—H10B	109.4
C3—C4—C5	106.2 (2)	C9—C10—H10B	109.4
C3—C4—H4A	110.5	H10A—C10—H10B	108
C5—C4—H4A	110.5	C12—C11—C10	110.7 (3)
C3—C4—H4B	110.5	C12—C11—H11A	109.5
C5—C4—H4B	110.5	C10—C11—H11A	109.5
H4A—C4—H4B	108.7	C12—C11—H11B	109.5
C6—C5—C4	107.0 (2)	C10—C11—H11B	109.5
C6—C5—H5A	110.3	H11A—C11—H11B	108.1
C4—C5—H5A	110.3	C11—C12—C13	112.4 (3)
C6—C5—H5B	110.3	C11—C12—H12A	109.1
C4—C5—H5B	110.3	C13—C12—H12A	109.1
H5A—C5—H5B	108.6	C11—C12—H12B	109.1
C7—C6—C5	105.6 (2)	C13—C12—H12B	109.1
C7—C6—H6A	110.6	H12A—C12—H12B	107.9
C5—C6—H6A	110.6	C8—C13—C12	111.7 (3)
C7—C6—H6B	110.6	C8—C13—H13A	109.3
C5—C6—H6B	110.6	C12—C13—H13A	109.3
H6A—C6—H6B	108.8	C8—C13—H13B	109.3
N1—C7—C3	126.3 (2)	C12—C13—H13B	109.3
N1—C7—C6	121.8 (2)	H13A—C13—H13B	107.9
C3—C7—C6	111.9 (2)
S2—C2—C7—N1	0.9 (2)	C1—S1—C2—S2	−5.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S2	0.93 (3)	2.24 (3)	3.026 (3)	142 (2)