Bis­[3-ethyl-1-methyl-5-(2-oxo­thia­zolidin-3-yl­carbonyl)­pyrazol-4-yl] di­sulfide

The title compound, C₂₀H₂₄N₆O₄S₄, has non-crystallographic twofold symmetry about the mid-point of the disulphide bond.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.037
• wR factor = 0.097
• Data-to-parameter ratio = 10.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.10 Ratio

Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.05 Ratio
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         S4
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C2

   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
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku and Rigaku/MSC, 2000–2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: WinGX (Farrugia, 1999); software used to prepare material for publication: CrystalStructure.

(I)

Crystal data

C20H24N6O4S4	F(000) = 1128
Mr = 540.69	Dx = 1.444 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 15829 reflections
a = 13.342 (1) Å	θ = 1.3–27.4°
b = 15.552 (1) Å	µ = 0.42 mm^−1
c = 12.0130 (8) Å	T = 295 K
β = 94.076 (2)°	Block, colorless
V = 2486.4 (3) Å^3	0.32 × 0.26 × 0.17 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	3436 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.039
ω scans	θmax = 27.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −16→17
Tmin = 0.809, Tmax = 0.931	k = −20→20
23803 measured reflections	l = −15→15
5666 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.037	w = 1/[0.0013Fo^2 + σ(Fo^2)]/(4Fo^2)
wR(F^2) = 0.097	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.31 e Å^−3
3436 reflections	Δρmin = −0.22 e Å^−3
331 parameters

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using reflections with F² > 2.0 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
S(1)	0.77703 (5)	0.64831 (4)	0.10365 (5)	0.0449 (2)
S(2)	0.67273 (6)	0.89651 (5)	0.24815 (7)	0.0636 (2)
S(3)	0.70588 (5)	0.53095 (4)	0.06410 (5)	0.0436 (2)
S(4)	0.81304 (7)	0.24531 (6)	0.06394 (9)	0.0820 (3)
O(1)	0.6995 (1)	0.6332 (1)	0.4533 (1)	0.0550 (6)
O(2)	0.8413 (1)	0.8099 (1)	0.2732 (2)	0.0664 (7)
O(3)	0.8154 (1)	0.4224 (1)	0.3873 (1)	0.0541 (6)
O(4)	0.6509 (1)	0.3246 (1)	0.1185 (2)	0.0690 (7)
N(1)	0.9793 (2)	0.5713 (1)	0.3374 (2)	0.0483 (6)
N(2)	0.9076 (1)	0.6043 (1)	0.3976 (2)	0.0415 (6)
N(3)	0.6993 (1)	0.7465 (1)	0.3372 (2)	0.0392 (5)
N(4)	0.5274 (2)	0.5236 (1)	0.3105 (2)	0.0459 (6)
N(5)	0.6033 (2)	0.4699 (1)	0.3473 (2)	0.0428 (6)
N(6)	0.8011 (1)	0.3595 (1)	0.2186 (2)	0.0435 (6)
C(1)	1.1116 (3)	0.5451 (4)	0.1624 (4)	0.149 (2)
C(2)	1.0047 (2)	0.5496 (2)	0.1381 (3)	0.068 (1)
C(3)	0.9457 (2)	0.5809 (2)	0.2314 (2)	0.0440 (7)
C(4)	0.8521 (2)	0.6218 (1)	0.2232 (2)	0.0371 (6)
C(5)	0.8299 (2)	0.6365 (1)	0.3325 (2)	0.0362 (6)
C(6)	0.9208 (2)	0.6028 (2)	0.5196 (2)	0.0633 (9)
C(7)	0.7401 (2)	0.6707 (1)	0.3814 (2)	0.0377 (7)
C(8)	0.6006 (2)	0.7723 (2)	0.3693 (2)	0.0487 (8)
C(9)	0.5640 (2)	0.8409 (2)	0.2888 (3)	0.069 (1)
C(10)	0.7533 (2)	0.8106 (2)	0.2868 (2)	0.0465 (8)
C(11)	0.3894 (2)	0.6372 (2)	0.1915 (3)	0.071 (1)
C(12)	0.4863 (2)	0.6129 (2)	0.1429 (2)	0.0562 (8)
C(13)	0.5507 (2)	0.5508 (2)	0.2109 (2)	0.0400 (7)
C(14)	0.6414 (2)	0.5139 (1)	0.1827 (2)	0.0371 (6)
C(15)	0.6724 (2)	0.4622 (1)	0.2729 (2)	0.0370 (6)
C(16)	0.5998 (3)	0.4301 (2)	0.4563 (2)	0.066 (1)
C(17)	0.7664 (2)	0.4132 (1)	0.2989 (2)	0.0389 (7)
C(18)	0.9024 (2)	0.3241 (2)	0.2385 (3)	0.0570 (9)
C(19)	0.9294 (2)	0.2854 (2)	0.1298 (3)	0.072 (1)
C(20)	0.7402 (2)	0.3170 (2)	0.1364 (2)	0.0523 (8)
H(1)	1.1406	0.5991	0.1432	0.180*
H(2)	1.1400	0.4999	0.1203	0.180*
H(3)	1.1256	0.5345	0.2407	0.180*
H(4)	0.9909	0.5876	0.0749	0.083*
H(5)	0.9818	0.4920	0.1184	0.083*
H(6)	0.8929	0.5507	0.5468	0.076*
H(7)	0.8873	0.6513	0.5495	0.075*
H(8)	0.9912	0.6053	0.5424	0.075*
H(9)	0.5555	0.7233	0.3656	0.059*
H(10)	0.6059	0.7950	0.4447	0.059*
H(11)	0.5198	0.8805	0.3240	0.083*
H(12)	0.5282	0.8150	0.2241	0.083*
H(13)	0.3373	0.5977	0.1663	0.085*
H(14)	0.3704	0.6944	0.1689	0.085*
H(15)	0.3991	0.6347	0.2714	0.085*
H(16)	0.4696	0.5868	0.0706	0.067*
H(17)	0.5249	0.6648	0.1334	0.067*
H(18)	0.6333	0.4663	0.5120	0.080*
H(19)	0.6331	0.3753	0.4557	0.080*
H(20)	0.5312	0.4220	0.4732	0.080*
H(21)	0.9490	0.3694	0.2626	0.068*
H(22)	0.9029	0.2798	0.2954	0.068*
H(23)	0.9775	0.2391	0.1421	0.087*
H(24)	0.9572	0.3293	0.0836	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S(1)	0.0481 (4)	0.0518 (4)	0.0343 (3)	−0.0017 (3)	0.0001 (3)	0.0091 (3)
S(2)	0.0660 (5)	0.0458 (4)	0.0805 (6)	0.0148 (4)	0.0160 (4)	0.0134 (4)
S(3)	0.0470 (4)	0.0540 (4)	0.0301 (3)	0.0004 (3)	0.0044 (3)	−0.0033 (3)
S(4)	0.0775 (6)	0.0754 (6)	0.0927 (7)	0.0158 (5)	0.0034 (5)	−0.0418 (5)
O(1)	0.062 (1)	0.059 (1)	0.046 (1)	0.0057 (9)	0.0177 (9)	0.0105 (9)
O(2)	0.047 (1)	0.050 (1)	0.105 (2)	0.0002 (9)	0.024 (1)	0.012 (1)
O(3)	0.058 (1)	0.061 (1)	0.041 (1)	0.009 (1)	−0.0073 (9)	−0.0001 (9)
O(4)	0.046 (1)	0.070 (1)	0.089 (2)	0.000 (1)	−0.008 (1)	−0.027 (1)
N(1)	0.039 (1)	0.054 (1)	0.052 (1)	0.010 (1)	0.002 (1)	−0.003 (1)
N(2)	0.042 (1)	0.047 (1)	0.035 (1)	0.0070 (9)	−0.0034 (9)	0.0001 (9)
N(3)	0.033 (1)	0.040 (1)	0.046 (1)	0.0044 (9)	0.0073 (9)	0.0015 (9)
N(4)	0.042 (1)	0.047 (1)	0.050 (1)	0.006 (1)	0.009 (1)	−0.001 (1)
N(5)	0.047 (1)	0.044 (1)	0.039 (1)	0.004 (1)	0.0095 (9)	0.0039 (9)
N(6)	0.038 (1)	0.046 (1)	0.046 (1)	0.0079 (9)	−0.0016 (9)	−0.007 (1)
C(1)	0.057 (2)	0.277 (8)	0.114 (4)	0.033 (4)	0.028 (2)	−0.063 (4)
C(2)	0.060 (2)	0.082 (2)	0.063 (2)	0.011 (2)	0.020 (2)	−0.006 (2)
C(3)	0.038 (1)	0.050 (2)	0.045 (1)	0.002 (1)	0.004 (1)	−0.003 (1)
C(4)	0.035 (1)	0.042 (1)	0.034 (1)	−0.001 (1)	0.000 (1)	0.003 (1)
C(5)	0.036 (1)	0.037 (1)	0.035 (1)	0.001 (1)	0.001 (1)	0.002 (1)
C(6)	0.071 (2)	0.080 (2)	0.037 (1)	0.019 (2)	−0.011 (1)	0.000 (1)
C(7)	0.040 (1)	0.039 (1)	0.034 (1)	0.001 (1)	0.000 (1)	−0.001 (1)
C(8)	0.036 (1)	0.051 (2)	0.061 (2)	0.003 (1)	0.010 (1)	−0.005 (1)
C(9)	0.047 (2)	0.061 (2)	0.099 (3)	0.014 (1)	0.002 (2)	0.008 (2)
C(10)	0.047 (2)	0.040 (1)	0.054 (2)	0.002 (1)	0.010 (1)	0.001 (1)
C(11)	0.046 (2)	0.068 (2)	0.097 (3)	0.013 (2)	0.002 (2)	0.008 (2)
C(12)	0.054 (2)	0.058 (2)	0.056 (2)	0.012 (1)	−0.001 (1)	0.002 (1)
C(13)	0.036 (1)	0.042 (1)	0.042 (1)	0.001 (1)	0.002 (1)	−0.002 (1)
C(14)	0.036 (1)	0.042 (1)	0.034 (1)	−0.002 (1)	0.001 (1)	−0.002 (1)
C(15)	0.038 (1)	0.038 (1)	0.035 (1)	0.000 (1)	0.005 (1)	−0.002 (1)
C(16)	0.074 (2)	0.077 (2)	0.050 (2)	0.012 (2)	0.024 (2)	0.018 (2)
C(17)	0.041 (1)	0.038 (1)	0.038 (1)	−0.000 (1)	0.004 (1)	0.003 (1)
C(18)	0.045 (2)	0.062 (2)	0.064 (2)	0.018 (1)	0.001 (1)	0.003 (1)
C(19)	0.056 (2)	0.081 (2)	0.080 (2)	0.024 (2)	0.012 (2)	−0.012 (2)
C(20)	0.055 (2)	0.045 (2)	0.057 (2)	0.003 (1)	0.002 (1)	−0.010 (1)

Geometric parameters (Å, º)

S(1)—S(3)	2.0962 (9)	C(11)—C(12)	1.504 (5)
S(1)—C(4)	1.741 (2)	C(12)—C(13)	1.496 (4)
S(2)—C(9)	1.787 (3)	C(13)—C(14)	1.402 (3)
S(2)—C(10)	1.756 (3)	C(14)—C(15)	1.389 (3)
S(3)—C(14)	1.736 (2)	C(15)—C(17)	1.482 (3)
S(4)—C(19)	1.803 (3)	C(18)—C(19)	1.505 (5)
S(4)—C(20)	1.751 (3)	C(1)—H(1)	0.9600
O(1)—C(7)	1.203 (3)	C(1)—H(2)	0.9600
O(2)—C(10)	1.197 (3)	C(1)—H(3)	0.9600
O(3)—C(17)	1.214 (3)	C(2)—H(4)	0.9700
O(4)—C(20)	1.201 (4)	C(2)—H(5)	0.9700
N(1)—N(2)	1.341 (3)	C(6)—H(6)	0.9600
N(1)—C(3)	1.329 (3)	C(6)—H(7)	0.9600
N(2)—C(5)	1.350 (3)	C(6)—H(8)	0.9600
N(2)—C(6)	1.463 (3)	C(8)—H(9)	0.9700
N(3)—C(7)	1.388 (3)	C(8)—H(10)	0.9700
N(3)—C(8)	1.455 (3)	C(9)—H(11)	0.9700
N(3)—C(10)	1.394 (3)	C(9)—H(12)	0.9700
N(4)—N(5)	1.361 (3)	C(11)—H(13)	0.9600
N(4)—C(13)	1.327 (3)	C(11)—H(14)	0.9600
N(5)—C(15)	1.335 (3)	C(11)—H(15)	0.9600
N(5)—C(16)	1.452 (4)	C(12)—H(16)	0.9700
N(6)—C(17)	1.381 (3)	C(12)—H(17)	0.9700
N(6)—C(18)	1.464 (3)	C(16)—H(18)	0.9600
N(6)—C(20)	1.399 (3)	C(16)—H(19)	0.9600
C(1)—C(2)	1.437 (5)	C(16)—H(20)	0.9600
C(2)—C(3)	1.496 (4)	C(18)—H(21)	0.9700
C(3)—C(4)	1.399 (3)	C(18)—H(22)	0.9700
C(4)—C(5)	1.385 (3)	C(19)—H(23)	0.9700
C(5)—C(7)	1.471 (3)	C(19)—H(24)	0.9700
C(8)—C(9)	1.499 (4)
C(4)—S(1)—S(3)	101.83 (8)	S(2)—C(9)—H(11)	109.9863
S(1)—S(3)—C(14)	100.95 (8)	S(2)—C(9)—H(12)	110.2471
S(1)—C(4)—C(3)	128.6 (2)	S(4)—C(19)—H(23)	110.4619
S(1)—C(4)—C(5)	126.4 (2)	S(4)—C(19)—H(24)	110.2139
C(10)—S(2)—C(9)	93.1 (1)	N(2)—C(6)—H(6)	109.4314
S(2)—C(9)—C(8)	106.7 (2)	N(2)—C(6)—H(7)	109.6376
S(2)—C(10)—O(2)	124.0 (2)	N(2)—C(6)—H(8)	109.3489
S(2)—C(10)—N(3)	109.5 (2)	N(3)—C(8)—H(9)	109.9495
S(3)—C(14)—C(13)	128.5 (2)	N(3)—C(8)—H(10)	109.9742
S(3)—C(14)—C(15)	126.2 (2)	N(5)—C(16)—H(18)	109.5131
C(20)—S(4)—C(19)	93.0 (2)	N(5)—C(16)—H(19)	109.1491
S(4)—C(19)—C(18)	105.5 (2)	N(5)—C(16)—H(20)	109.7462
S(4)—C(20)—O(4)	123.5 (2)	N(6)—C(18)—H(21)	109.9803
S(4)—C(20)—N(6)	109.7 (2)	N(6)—C(18)—H(22)	110.0135
O(1)—C(7)—N(3)	120.2 (2)	C(1)—C(2)—H(4)	108.6237
O(1)—C(7)—C(5)	122.2 (2)	H(1)—C(1)—C(2)	108.6333
O(2)—C(10)—N(3)	126.5 (2)	H(3)—C(1)—C(2)	109.1830
O(3)—C(17)—N(6)	119.7 (2)	C(1)—C(2)—H(5)	107.1952
O(3)—C(17)—C(15)	121.3 (2)	H(2)—C(1)—C(2)	110.5894
O(4)—C(20)—N(6)	126.7 (3)	H(3)—C(1)—H(1)	109.4617
C(3)—N(1)—N(2)	105.6 (2)	H(2)—C(1)—H(1)	109.4732
N(1)—N(2)—C(5)	112.2 (2)	H(3)—C(1)—H(2)	109.4802
N(1)—N(2)—C(6)	119.6 (2)	H(4)—C(2)—C(3)	107.8802
N(1)—C(3)—C(2)	121.5 (2)	H(5)—C(2)—C(3)	108.0228
N(1)—C(3)—C(4)	110.9 (2)	H(5)—C(2)—H(4)	109.4563
N(2)—C(5)—C(4)	106.3 (2)	H(7)—C(6)—H(6)	109.4709
N(2)—C(5)—C(7)	121.0 (2)	H(8)—C(6)—H(6)	109.4704
C(6)—N(2)—C(5)	128.3 (2)	H(8)—C(6)—H(7)	109.4681
N(3)—C(7)—C(5)	117.5 (2)	H(9)—C(8)—C(9)	110.9077
C(10)—N(3)—C(7)	125.0 (2)	H(10)—C(8)—C(9)	109.9564
C(8)—N(3)—C(7)	118.1 (2)	C(8)—C(9)—H(11)	110.5510
C(10)—N(3)—C(8)	115.0 (2)	C(8)—C(9)—H(12)	109.8932
N(3)—C(8)—C(9)	106.6 (2)	H(10)—C(8)—H(9)	109.4618
C(13)—N(4)—N(5)	105.8 (2)	H(12)—C(9)—H(11)	109.4608
N(4)—N(5)—C(15)	111.8 (2)	C(11)—C(12)—H(17)	108.3413
N(4)—N(5)—C(16)	119.0 (2)	C(11)—C(12)—H(16)	107.7252
N(4)—C(13)—C(14)	110.4 (2)	H(13)—C(11)—C(12)	109.8317
N(4)—C(13)—C(12)	122.4 (2)	H(15)—C(11)—C(12)	108.6618
N(5)—C(15)—C(14)	106.8 (2)	H(14)—C(11)—C(12)	109.9129
N(5)—C(15)—C(17)	121.3 (2)	H(15)—C(11)—H(13)	109.4726
C(16)—N(5)—C(15)	129.3 (2)	H(14)—C(11)—H(13)	109.4727
N(6)—C(17)—C(15)	118.9 (2)	H(15)—C(11)—H(14)	109.4726
C(20)—N(6)—C(17)	124.9 (2)	H(17)—C(12)—C(13)	108.1998
C(18)—N(6)—C(17)	117.7 (2)	H(16)—C(12)—C(13)	107.7678
C(20)—N(6)—C(18)	114.9 (2)	H(17)—C(12)—H(16)	109.4632
N(6)—C(18)—C(19)	106.5 (2)	H(19)—C(16)—H(18)	109.4736
C(1)—C(2)—C(3)	115.6 (3)	H(20)—C(16)—H(18)	109.4766
C(2)—C(3)—C(4)	127.6 (2)	H(20)—C(16)—H(19)	109.4680
C(3)—C(4)—C(5)	105.0 (2)	H(21)—C(18)—C(19)	111.1785
C(4)—C(5)—C(7)	132.4 (2)	H(22)—C(18)—C(19)	109.7024
C(11)—C(12)—C(13)	115.3 (3)	C(18)—C(19)—H(23)	111.2263
C(12)—C(13)—C(14)	127.2 (2)	C(18)—C(19)—H(24)	109.8968
C(13)—C(14)—C(15)	105.2 (2)	H(22)—C(18)—H(21)	109.4644
C(14)—C(15)—C(17)	131.5 (2)	H(24)—C(19)—H(23)	109.4605