(2R)-N-{3-[Bis(methyl­sulfan­yl)methyl­eneamino]­propiono­yl}bornane-10,2-sultam

Woźniak, D.; Szymańska, A.; Sikorski, A.; Konitz, A.; Lis, T.

doi:10.1107/S1600536805041541

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(2R)-N-{3-[Bis(methylsulfanyl)methyleneamino]propionoyl}bornane-10,2-sultam

D. Woźniak, A. Szymańska, A. Sikorski, A. Konitz and T. Lis

In the title compound, C₁₆H₂₆N₂O₃S₃, adjacent molecules are arranged in a head-to-tail manner and linked via weak C—H

S interactions, forming helical chains parallel to the a axis. These chains are connected via C—H

O interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805041541/ob6594sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805041541/ob6594Isup2.hkl Contains datablock I

CCDC reference: 296620

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.025
wR factor = 0.062
Data-to-parameter ratio = 24.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.60 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.07 Ratio
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3A    ..  S14     ..       2.95 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           30.00
           From the CIF: _reflns_number_total               5320
           Count of symmetry unique reflns         3067
           Completeness (_total/calc)            173.46%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2253
           Fraction of Friedel pairs measured     0.735
           Are heavy atom types Z>Si present        yes

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

β-Amino acids are a key part of many natural products displaying antibiotic, antifungal and cytotoxic properties (Cardillo & Tomasini, 1996), precursors of β-lactam antibiotics (Georg, 1993), and peptidomimetics showing remarkable resistance for enzymatic degradation (Steer et al., 2000). β-Amino acids are also very interesting objects of studies because of their tendency to form highly stable helical structures: 14-helix, 12-helix, 10/12-helix for penta-, hexa- and heptamers, composed of appropriately substituted β-amino acids (Seebach et al., 1998; Cheng et al., 2001). The stability of above structures is higher than those of similar ones formed by α-amino acids.

Even though β-amino acids can be obtained from natural sources and via chemical synthesis (Liu & Sibi, 2002), taking into account their significance and their further applications as peptide mimetics, there is a need for elaboration of new, effective and stereoselective methods of their preparation. One of the possible synthetic ways leading to the above compounds involves synthesis of simple precursor (e.g. β-alanine) attached to a chiral auxiliary group. Among many chiral auxiliaries, bornane-10,2-sultam is one of the most popular and effective groups to create new chiral centres. This group was introduced by Oppolzer et al. (1984), and henceforth has been widely used for synthesis of many compounds (Oppolzer, 1990; Szymańska et al., 2000). We applied the Schiff base obtained from β-alanine and Oppolzer's sultam for the synthesis of some β²-substituted β-amino acids (Woźniak et al., 2005). For this purpose we modified the methodology described by Ponsinet et al. (2000). The precursor was chosen on the basis of the simplicity of its synthesis, the very high asymmetric induction characteristic for the sultam moiety and the high tendency of N-acylsultam derivatives to be crystalline.

In the title compound, (I), bond lengths and angles are typical for substituted bornane-10,2-sultam (Hughes et al., 1999; Raczko et al., 2000; Szymański et al., 2001) (Fig. 1 and Table 1). The cyclohexane ring adopts a fairly regular boat conformation, with ring puckering parameters Q = 0.993 (2) Å, θ = 88.65 (7)° and ϕ = 355.21 (7)° (Cremer & Pople, 1975) and asymmetry parameter ΔC_s(C1) = 9.4 (1)° (Duax et al., 1976). Adjacent molecules of (I) are arranged in a head-to-tail manner and linked via weak C—H···S interactions (Table 2), forming helical chains parallel to the a axis (Fig. 2). These chains are connected via C—H···O interactions (Table 2).

Experimental top

Compound (I) was synthesized from bornane-10,2-sultam and methyl 3-{[bis(methyltio)methylene]amino}propionate, according to the procedure given by Oppolzer et al. (1989). Such obtained compound can be, after enolatization by treatment with either n-butyllithium or lithium diisopropylamide at 195 K, alkylated by selected alkyl halides yielding precursors of β²-amino acids (superscript 2 denotes the position of the introduced group α with reference to the carboxyl group). Crystals of (I) suitable for X-ray study were grown from an ethanol solution by slow evaporation at room temperature (m.p. 363–364 K).

Computing details top

Data collection: KM-4 CCD Software (Oxford Diffraction, 2003); cell refinement: KM-4 CCD Software; data reduction: KM-4 CCD Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-labelling scheme and 50% probability displacement ellipsoids.
	Fig. 2. The arrangement of the molecules of (I) in the unit cell. The C—H···O and C—H···S interactions are represented by dashed lines. H atoms not involved in these interactions have been omitted.

(2R)-N-{3-[Bis(methylsulfanyl)methylene]aminopropionoyl}bornane-10,2-sultam top

Crystal data top

C₁₆H₂₆N₂O₃S₃	F(000) = 832
M_r = 390.57	D_x = 1.398 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 16987 reflections
a = 7.742 (2) Å	θ = 3–30°
b = 12.348 (3) Å	µ = 0.42 mm⁻¹
c = 19.405 (3) Å	T = 100 K
V = 1855.1 (7) Å³	Prism, colourless
Z = 4	0.5 × 0.4 × 0.3 mm

Data collection top

Kuma KM-4 CCD diffractometer	5197 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 30.0°, θ_min = 3.5°
ω scans	h = −10→10
23438 measured reflections	k = −17→17
5320 independent reflections	l = −27→25

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.025	H-atom parameters constrained
wR(F²) = 0.062	w = 1/[σ²(F_o²) + (0.0336P)² + 0.344P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.007
5320 reflections	Δρ_max = 0.34 e Å⁻³
221 parameters	Δρ_min = −0.28 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 2253 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (4)

Crystal data top

C₁₆H₂₆N₂O₃S₃	V = 1855.1 (7) Å³
M_r = 390.57	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.742 (2) Å	µ = 0.42 mm⁻¹
b = 12.348 (3) Å	T = 100 K
c = 19.405 (3) Å	0.5 × 0.4 × 0.3 mm

Data collection top

Kuma KM-4 CCD diffractometer	5197 reflections with I > 2σ(I)
23438 measured reflections	R_int = 0.035
5320 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	H-atom parameters constrained
wR(F²) = 0.062	Δρ_max = 0.34 e Å⁻³
S = 1.08	Δρ_min = −0.28 e Å⁻³
5320 reflections	Absolute structure: Flack (1983), 2253 Friedel pairs
221 parameters	Absolute structure parameter: 0.02 (4)
0 restraints

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.51915 (13)	0.67071 (9)	0.88913 (6)	0.01110 (19)
C2	0.49885 (16)	0.55731 (9)	0.92132 (6)	0.0151 (2)
H2A	0.3757	0.5393	0.9290	0.018*
H2B	0.5618	0.5519	0.9656	0.018*
C3	0.58097 (17)	0.48228 (10)	0.86535 (6)	0.0171 (2)
H3A	0.6854	0.4455	0.8832	0.021*
H3B	0.4974	0.4270	0.8494	0.021*
C4	0.62729 (16)	0.56221 (10)	0.80667 (6)	0.0153 (2)
H4A	0.6390	0.5275	0.7603	0.018*
C5	0.78750 (15)	0.62777 (10)	0.82945 (6)	0.0150 (2)
H5A	0.8289	0.6758	0.7921	0.018*
H5B	0.8828	0.5794	0.8440	0.018*
C6	0.71568 (14)	0.69419 (9)	0.89122 (6)	0.0116 (2)
H6A	0.7661	0.6668	0.9354	0.014*
N7	0.73476 (12)	0.81367 (8)	0.88720 (5)	0.01266 (18)
C8	0.89772 (14)	0.86113 (9)	0.88450 (6)	0.0124 (2)
C9	0.90309 (14)	0.98358 (9)	0.88196 (6)	0.0147 (2)
H9A	0.8628	1.0127	0.9267	0.018*
H9B	0.8226	1.0093	0.8458	0.018*
C10	1.08343 (16)	1.02783 (10)	0.86693 (7)	0.0164 (2)
H10A	1.1596	1.0163	0.9072	0.020*
H10B	1.1342	0.9896	0.8269	0.020*
N11	1.06878 (14)	1.14448 (8)	0.85198 (5)	0.01622 (19)
C12	1.08624 (15)	1.21226 (10)	0.90071 (6)	0.0149 (2)
S13	1.06005 (4)	1.35316 (2)	0.886320 (15)	0.01729 (6)
S14	1.13436 (5)	1.17486 (3)	0.987090 (17)	0.02570 (8)
C15	1.00471 (19)	1.35206 (11)	0.79608 (7)	0.0211 (2)
H15A	0.9723	1.4253	0.7815	0.032*
H15B	0.9073	1.3028	0.7885	0.032*
H15C	1.1044	1.3275	0.7691	0.032*
C16	1.1389 (2)	1.30060 (12)	1.03450 (8)	0.0289 (3)
H16A	1.1732	1.2864	1.0823	0.043*
H16B	1.0238	1.3336	1.0338	0.043*
H16C	1.2222	1.3501	1.0131	0.043*
C17	0.48111 (15)	0.64785 (10)	0.81113 (6)	0.0146 (2)
C18	0.29864 (17)	0.60251 (12)	0.79903 (7)	0.0236 (3)
H18A	0.2821	0.5885	0.7498	0.035*
H18B	0.2128	0.6553	0.8148	0.035*
H18C	0.2847	0.5349	0.8248	0.035*
C19	0.50311 (19)	0.74367 (11)	0.76128 (7)	0.0214 (3)
H19A	0.4999	0.7172	0.7137	0.032*
H19B	0.6142	0.7792	0.7700	0.032*
H19C	0.4092	0.7957	0.7684	0.032*
C20	0.42524 (15)	0.76273 (9)	0.92518 (6)	0.0158 (2)
H20A	0.4059	0.7446	0.9743	0.019*
H20B	0.3118	0.7757	0.9031	0.019*
S21	0.55856 (4)	0.88043 (2)	0.917945 (16)	0.01488 (6)
O22	0.49880 (12)	0.95521 (8)	0.86658 (6)	0.0250 (2)
O23	0.59643 (13)	0.92319 (8)	0.98528 (5)	0.0258 (2)
O24	1.02565 (11)	0.80390 (7)	0.88246 (5)	0.01985 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0087 (4)	0.0125 (5)	0.0121 (4)	−0.0013 (4)	0.0005 (3)	−0.0006 (4)
C2	0.0164 (5)	0.0139 (5)	0.0150 (5)	−0.0007 (4)	0.0034 (4)	0.0007 (4)
C3	0.0187 (6)	0.0128 (5)	0.0199 (5)	−0.0027 (4)	0.0044 (4)	−0.0015 (4)
C4	0.0164 (5)	0.0158 (5)	0.0136 (5)	−0.0035 (4)	0.0027 (4)	−0.0037 (4)
C5	0.0119 (5)	0.0144 (5)	0.0187 (5)	−0.0011 (4)	0.0037 (4)	−0.0034 (4)
C6	0.0094 (4)	0.0108 (5)	0.0146 (5)	−0.0009 (4)	−0.0013 (4)	−0.0010 (4)
N7	0.0082 (4)	0.0104 (4)	0.0194 (4)	0.0005 (3)	0.0000 (3)	−0.0015 (4)
C8	0.0106 (4)	0.0128 (5)	0.0139 (5)	−0.0014 (4)	−0.0019 (4)	−0.0012 (4)
C9	0.0119 (5)	0.0117 (5)	0.0206 (5)	−0.0003 (4)	−0.0002 (4)	0.0004 (4)
C10	0.0142 (5)	0.0129 (5)	0.0223 (6)	−0.0022 (4)	0.0026 (4)	−0.0036 (4)
N11	0.0159 (5)	0.0142 (4)	0.0186 (4)	−0.0022 (4)	0.0013 (4)	−0.0006 (4)
C12	0.0143 (5)	0.0128 (5)	0.0176 (5)	−0.0031 (4)	−0.0007 (4)	0.0026 (4)
S13	0.02205 (14)	0.01235 (12)	0.01746 (13)	−0.00150 (11)	−0.00094 (11)	−0.00015 (10)
S14	0.0432 (2)	0.01505 (14)	0.01882 (14)	−0.00273 (14)	−0.01004 (14)	0.00058 (12)
C15	0.0271 (6)	0.0195 (6)	0.0167 (5)	0.0039 (5)	−0.0012 (5)	0.0008 (5)
C16	0.0426 (9)	0.0218 (6)	0.0224 (6)	−0.0012 (6)	−0.0109 (6)	−0.0064 (5)
C17	0.0139 (5)	0.0169 (5)	0.0130 (5)	−0.0031 (4)	−0.0017 (4)	−0.0013 (4)
C18	0.0179 (6)	0.0284 (7)	0.0246 (6)	−0.0071 (5)	−0.0075 (5)	−0.0024 (6)
C19	0.0238 (6)	0.0245 (6)	0.0157 (5)	−0.0036 (5)	−0.0054 (5)	0.0054 (5)
C20	0.0115 (5)	0.0138 (5)	0.0219 (5)	−0.0002 (4)	0.0039 (4)	−0.0024 (4)
S21	0.01014 (11)	0.01224 (12)	0.02226 (13)	0.00152 (10)	0.00221 (11)	−0.00297 (10)
O22	0.0137 (4)	0.0186 (4)	0.0426 (6)	0.0050 (3)	0.0010 (4)	0.0091 (4)
O23	0.0230 (5)	0.0267 (5)	0.0277 (5)	−0.0036 (4)	0.0051 (4)	−0.0155 (4)
O24	0.0108 (4)	0.0146 (4)	0.0342 (5)	0.0014 (3)	−0.0018 (3)	−0.0015 (4)

Geometric parameters (Å, º) top

C1—C20	1.5197 (16)	C10—H10A	0.9900
C1—C2	1.5413 (16)	C10—H10B	0.9900
C1—C6	1.5495 (15)	N11—C12	1.2700 (16)
C1—C17	1.5676 (16)	C12—S13	1.7738 (13)
C2—C3	1.5627 (17)	C12—S14	1.7780 (13)
C2—H2A	0.9900	S13—C15	1.8028 (13)
C2—H2B	0.9900	S14—C16	1.8050 (15)
C3—C4	1.5490 (17)	C15—H15A	0.9800
C3—H3A	0.9900	C15—H15B	0.9800
C3—H3B	0.9900	C15—H15C	0.9800
C4—C5	1.5456 (17)	C16—H16A	0.9800
C4—C17	1.5513 (18)	C16—H16B	0.9800
C4—H4A	1.0000	C16—H16C	0.9800
C5—C6	1.5553 (16)	C17—C18	1.5376 (17)
C5—H5A	0.9900	C17—C19	1.5377 (17)
C5—H5B	0.9900	C18—H18A	0.9800
C6—N7	1.4848 (15)	C18—H18B	0.9800
C6—H6A	1.0000	C18—H18C	0.9800
N7—C8	1.3921 (14)	C19—H19A	0.9800
N7—S21	1.7019 (10)	C19—H19B	0.9800
C8—O24	1.2173 (14)	C19—H19C	0.9800
C8—C9	1.5134 (16)	C20—S21	1.7880 (12)
C9—C10	1.5273 (16)	C20—H20A	0.9900
C9—H9A	0.9900	C20—H20B	0.9900
C9—H9B	0.9900	S21—O22	1.4353 (11)
C10—N11	1.4737 (16)	S21—O23	1.4395 (10)

C20—C1—C2	116.35 (9)	N11—C10—H10B	110.0
C20—C1—C6	108.53 (9)	C9—C10—H10B	110.0
C2—C1—C6	105.04 (9)	H10A—C10—H10B	108.4
C20—C1—C17	119.29 (10)	C12—N11—C10	119.31 (11)
C2—C1—C17	102.04 (9)	N11—C12—S13	121.13 (9)
C6—C1—C17	104.10 (9)	N11—C12—S14	123.58 (10)
C1—C2—C3	102.44 (9)	S13—C12—S14	115.28 (7)
C1—C2—H2A	111.3	C12—S13—C15	99.94 (6)
C3—C2—H2A	111.3	C12—S14—C16	105.14 (7)
C1—C2—H2B	111.3	S13—C15—H15A	109.5
C3—C2—H2B	111.3	S13—C15—H15B	109.5
H2A—C2—H2B	109.2	H15A—C15—H15B	109.5
C4—C3—C2	103.14 (10)	S13—C15—H15C	109.5
C4—C3—H3A	111.1	H15A—C15—H15C	109.5
C2—C3—H3A	111.1	H15B—C15—H15C	109.5
C4—C3—H3B	111.1	S14—C16—H16A	109.5
C2—C3—H3B	111.1	S14—C16—H16B	109.5
H3A—C3—H3B	109.1	H16A—C16—H16B	109.5
C5—C4—C3	108.01 (10)	S14—C16—H16C	109.5
C5—C4—C17	102.27 (9)	H16A—C16—H16C	109.5
C3—C4—C17	102.97 (10)	H16B—C16—H16C	109.5
C5—C4—H4A	114.1	C18—C17—C19	106.61 (10)
C3—C4—H4A	114.1	C18—C17—C4	114.43 (11)
C17—C4—H4A	114.1	C19—C17—C4	114.12 (10)
C4—C5—C6	102.11 (9)	C18—C17—C1	112.68 (10)
C4—C5—H5A	111.3	C19—C17—C1	116.61 (10)
C6—C5—H5A	111.3	C4—C17—C1	92.26 (9)
C4—C5—H5B	111.3	C17—C18—H18A	109.5
C6—C5—H5B	111.3	C17—C18—H18B	109.5
H5A—C5—H5B	109.2	H18A—C18—H18B	109.5
N7—C6—C1	106.39 (9)	C17—C18—H18C	109.5
N7—C6—C5	116.61 (10)	H18A—C18—H18C	109.5
C1—C6—C5	103.42 (9)	H18B—C18—H18C	109.5
N7—C6—H6A	110.0	C17—C19—H19A	109.5
C1—C6—H6A	110.0	C17—C19—H19B	109.5
C5—C6—H6A	110.0	H19A—C19—H19B	109.5
C8—N7—C6	120.69 (9)	C17—C19—H19C	109.5
C8—N7—S21	122.39 (8)	H19A—C19—H19C	109.5
C6—N7—S21	112.53 (7)	H19B—C19—H19C	109.5
O24—C8—N7	119.62 (10)	C1—C20—S21	107.18 (8)
O24—C8—C9	123.82 (10)	C1—C20—H20A	110.3
N7—C8—C9	116.53 (9)	S21—C20—H20A	110.3
C8—C9—C10	112.87 (10)	C1—C20—H20B	110.3
C8—C9—H9A	109.0	S21—C20—H20B	110.3
C10—C9—H9A	109.0	H20A—C20—H20B	108.5
C8—C9—H9B	109.0	O22—S21—O23	117.39 (7)
C10—C9—H9B	109.0	O22—S21—N7	109.06 (6)
H9A—C9—H9B	107.8	O23—S21—N7	109.43 (6)
N11—C10—C9	108.47 (10)	O22—S21—C20	113.04 (6)
N11—C10—H10A	110.0	O23—S21—C20	110.14 (6)
C9—C10—H10A	110.0	N7—S21—C20	95.54 (5)

C20—C1—C2—C3	170.21 (10)	S14—C12—S13—C15	−177.44 (7)
C6—C1—C2—C3	−69.77 (11)	N11—C12—S14—C16	−178.52 (12)
C17—C1—C2—C3	38.61 (11)	S13—C12—S14—C16	0.53 (10)
C1—C2—C3—C4	−3.28 (12)	C5—C4—C17—C18	−173.37 (10)
C2—C3—C4—C5	74.14 (12)	C3—C4—C17—C18	−61.36 (12)
C2—C3—C4—C17	−33.57 (12)	C5—C4—C17—C19	63.44 (12)
C3—C4—C5—C6	−66.00 (12)	C3—C4—C17—C19	175.45 (10)
C17—C4—C5—C6	42.20 (11)	C5—C4—C17—C1	−57.15 (10)
C20—C1—C6—N7	−33.23 (12)	C3—C4—C17—C1	54.86 (10)
C2—C1—C6—N7	−158.32 (9)	C20—C1—C17—C18	−69.21 (14)
C17—C1—C6—N7	94.81 (10)	C2—C1—C17—C18	60.59 (12)
C20—C1—C6—C5	−156.61 (9)	C6—C1—C17—C18	169.69 (10)
C2—C1—C6—C5	78.30 (11)	C20—C1—C17—C19	54.58 (14)
C17—C1—C6—C5	−28.57 (11)	C2—C1—C17—C19	−175.62 (10)
C4—C5—C6—N7	−124.19 (10)	C6—C1—C17—C19	−66.53 (13)
C4—C5—C6—C1	−7.82 (11)	C20—C1—C17—C4	173.08 (10)
C1—C6—N7—C8	−176.83 (10)	C2—C1—C17—C4	−57.12 (10)
C5—C6—N7—C8	−62.12 (14)	C6—C1—C17—C4	51.98 (10)
C1—C6—N7—S21	26.16 (11)	C2—C1—C20—S21	144.62 (9)
C5—C6—N7—S21	140.87 (8)	C6—C1—C20—S21	26.49 (11)
C6—N7—C8—O24	3.16 (17)	C17—C1—C20—S21	−92.37 (11)
S21—N7—C8—O24	157.87 (10)	C8—N7—S21—O22	76.99 (11)
C6—N7—C8—C9	−178.79 (10)	C6—N7—S21—O22	−126.45 (9)
S21—N7—C8—C9	−24.08 (15)	C8—N7—S21—O23	−52.65 (11)
O24—C8—C9—C10	7.66 (17)	C6—N7—S21—O23	103.92 (9)
N7—C8—C9—C10	−170.31 (10)	C8—N7—S21—C20	−166.30 (10)
C8—C9—C10—N11	168.95 (10)	C6—N7—S21—C20	−9.73 (9)
C9—C10—N11—C12	92.48 (13)	C1—C20—S21—O22	103.14 (9)
C10—N11—C12—S13	−177.08 (9)	C1—C20—S21—O23	−123.34 (8)
C10—N11—C12—S14	1.92 (16)	C1—C20—S21—N7	−10.29 (9)
N11—C12—S13—C15	1.64 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···S14ⁱ	0.99	2.95	3.484 (2)	115 (1)
C20—H20B···O24ⁱⁱ	0.99	2.28	3.242 (2)	164 (1)

Symmetry codes: (i) x−1/2, −y+3/2, −z+2; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₆N₂O₃S₃
M_r	390.57
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	7.742 (2), 12.348 (3), 19.405 (3)
V (Å³)	1855.1 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.5 × 0.4 × 0.3

Data collection
Diffractometer	Kuma KM-4 CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	23438, 5320, 5197
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.062, 1.08
No. of reflections	5320
No. of parameters	221
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.28
Absolute structure	Flack (1983), 2253 Friedel pairs
Absolute structure parameter	0.02 (4)

Computer programs: KM-4 CCD Software (Oxford Diffraction, 2003), KM-4 CCD Software, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97 and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

N7—C8	1.3921 (14)	C12—S14	1.7780 (13)
N7—S21	1.7019 (10)	C20—S21	1.7880 (12)
C10—N11	1.4737 (16)	S21—O22	1.4353 (11)
N11—C12	1.2700 (16)	S21—O23	1.4395 (10)
C12—S13	1.7738 (13)

C1—C2—C3—C4	−3.28 (12)	C1—C6—N7—S21	26.16 (11)
C20—C1—C6—N7	−33.23 (12)	C5—C6—N7—S21	140.87 (8)
C4—C5—C6—C1	−7.82 (11)	S21—N7—C8—C9	−24.08 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···S14ⁱ	0.99	2.95	3.484 (2)	115 (1)
C20—H20B···O24ⁱⁱ	0.99	2.28	3.242 (2)	164 (1)

Symmetry codes: (i) x−1/2, −y+3/2, −z+2; (ii) x−1, y, z.

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