New polysubstituted monoterpenic thia­zolidinones: synthesis, spectroscopic and crystal structure studies

The synthesis of three new polysubstituted monoterpenic thia­zolidin-4-ones, namely (Z)-3-methyl-2-{(E)-[(1R,4R)-1,7,7-tri­methylbi­cyclo­[2.2.1]heptan-2-yl­idene]hydrazinyl­idene}thia­zolidin-4-one, C₁₄H₂₁N₃OS (2), (2Z,5Z)-5-[(di­methyl­amino)­methyl­idene]-2-{(E)-[(1R,4R)-1,7,7-tri­methylbi­cyclo­[2.2.1]heptan-2-yl­idene]hydrazinyl­idene}thia­zolidin-4-one, C₁₆H₂₄N₄OS (3), and (2Z,5Z)-5-[(di­methyl­amino)­methyl­idene]-3-methyl-2-{(E)-[(1R,4R)-1,7,7-tri­methylbi­cyclo­[2.2.1]heptan-2-yl­idene]hydrazinyl­idene}thia­zolidin-4-one, C₁₇H₂₆N₄OS (4), is reported, starting from the corresponding thio­semicarbazones obtained from naturally occurring (R)-camphor. All the newly obtained thia­zolidin-4-ones have been fully characterized by HRMS and ¹H and ¹³C (1D and 2D) NMR spectroscopy. Two of them, i.e. 2 and 3, were identified by single-crystal X-ray crystallography, confirming the synthetic pathway and the spectroscopic analyses. In 3, there are two roughly identical mol­ecules within the asymmetric unit with the same absolute configuration. These two mol­ecules are linked through N—H...O hydrogen bonds, building an R₂²(8) graph-set motif.

Computing details

Data collection: CrysAlis PRO (Agilent, 2014) for (2); APEX2 (Bruker, 2014) for (3). Cell refinement: CrysAlis PRO (Agilent, 2014) for (2); SAINT (Bruker, 2014) for (3). Data reduction: CrysAlis PRO (Agilent, 2014) for (2); SAINT (Bruker, 2014) for (3). Program(s) used to solve structure: SHELXT (Sheldrick, 2015a) for (2); SIR97 (Altomare et al., 1999) for (3). For both structures, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009). Software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) for (2); SHELXL2014 (Sheldrick, 2015) for (3).

(Z)-3-Methyl-2-{(E)-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene]hydrazinylidene}thiazolidin-4-one (2)

Crystal data

C14H21N3OS	Dx = 1.266 Mg m^−3
Mr = 279.40	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 4325 reflections
a = 7.1606 (4) Å	θ = 3.5–29.2°
b = 7.2405 (3) Å	µ = 0.22 mm^−1
c = 28.2842 (14) Å	T = 173 K
V = 1466.43 (13) Å^3	Box, yellow
Z = 4	0.5 × 0.5 × 0.24 mm
F(000) = 600

Data collection

Agilent Xcalibu, Eos Gemini ultra diffractometer	2832 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2712 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 16.1978 pixels mm^-1	θmax = 26.4°, θmin = 3.2°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −8→9
Tmin = 0.648, Tmax = 1.000	l = −33→35
8749 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.034	w = 1/[σ^2(Fo^2) + (0.0325P)^2 + 0.3996P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.078	(Δ/σ)max < 0.001
S = 1.12	Δρmax = 0.20 e Å^−3
2832 reflections	Δρmin = −0.26 e Å^−3
176 parameters	Absolute structure: Flack x determined using 979 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: 0.03 (3)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 1.0Å (methine), 0.99Å(methylene) with U_iso(H) = 1.2U_eq(C) and 0.98Å (methyl) with U_iso(H) = 1.2U_eq(C).

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

	x	y	z	Uiso*/Ueq
C1	0.1977 (3)	0.5139 (3)	0.33344 (7)	0.0191 (5)
C2	0.2241 (3)	0.4388 (3)	0.38288 (7)	0.0205 (5)
C2'	0.2332 (3)	0.5584 (3)	0.49688 (8)	0.0225 (5)
C3	0.2527 (4)	0.2324 (3)	0.37895 (7)	0.0252 (5)
H3A	0.153641	0.163186	0.395754	0.030*
H3B	0.376342	0.194659	0.391258	0.030*
C4'	0.2348 (4)	0.6307 (3)	0.57771 (8)	0.0313 (6)
C4	0.2395 (3)	0.2057 (3)	0.32500 (7)	0.0248 (5)
H4	0.296452	0.088441	0.313093	0.030*
C5	0.0322 (3)	0.2309 (4)	0.31226 (9)	0.0311 (6)
H5A	−0.049160	0.158709	0.333677	0.037*
H5B	0.007414	0.193482	0.279184	0.037*
C5'	0.2224 (4)	0.8215 (3)	0.55657 (8)	0.0342 (6)
H5'1	0.331675	0.896022	0.566381	0.041*
H5'2	0.107843	0.884216	0.567775	0.041*
C6	0.0028 (3)	0.4399 (4)	0.31904 (9)	0.0258 (5)
H6A	−0.090232	0.464184	0.344164	0.031*
H6B	−0.040214	0.498229	0.289320	0.031*
C6'	0.2552 (4)	0.3016 (3)	0.55360 (8)	0.0350 (6)
H6'1	0.262195	0.283939	0.587910	0.052*
H6'2	0.367307	0.250195	0.538731	0.052*
H6'3	0.144355	0.238456	0.541265	0.052*
C7	0.3302 (3)	0.3839 (3)	0.30525 (8)	0.0210 (5)
C8	0.2220 (4)	0.7210 (3)	0.32843 (8)	0.0278 (5)
H8A	0.126527	0.784495	0.347198	0.042*
H8B	0.208838	0.755808	0.295109	0.042*
H8C	0.346254	0.756547	0.339730	0.042*
C9	0.5350 (3)	0.4078 (4)	0.31915 (11)	0.0326 (6)
H9A	0.608526	0.305515	0.306151	0.049*
H9B	0.545951	0.408163	0.353690	0.049*
H9C	0.581950	0.524967	0.306528	0.049*
C10	0.3155 (4)	0.4025 (3)	0.25156 (8)	0.0289 (6)
H10A	0.361196	0.524411	0.241914	0.043*
H10B	0.184820	0.388667	0.241908	0.043*
H10C	0.391133	0.306428	0.236430	0.043*
N3'	0.2427 (3)	0.4982 (3)	0.54306 (6)	0.0248 (4)
N11	0.2354 (3)	0.4441 (2)	0.46247 (6)	0.0269 (4)
N12	0.2173 (3)	0.5427 (2)	0.41931 (6)	0.0244 (4)
O7'	0.2374 (4)	0.5983 (3)	0.61961 (6)	0.0509 (6)
S1'	0.21740 (9)	0.79994 (8)	0.49270 (2)	0.02633 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0198 (11)	0.0190 (10)	0.0185 (10)	0.0012 (10)	−0.0010 (9)	0.0004 (8)
C2	0.0188 (10)	0.0215 (10)	0.0212 (10)	−0.0032 (10)	−0.0017 (10)	0.0017 (8)
C2'	0.0196 (11)	0.0255 (10)	0.0225 (11)	−0.0009 (10)	−0.0014 (10)	0.0014 (9)
C3	0.0293 (13)	0.0203 (10)	0.0260 (11)	−0.0005 (11)	−0.0010 (10)	0.0034 (8)
C4'	0.0332 (14)	0.0374 (13)	0.0234 (12)	0.0033 (13)	−0.0020 (11)	−0.0056 (9)
C4	0.0320 (13)	0.0171 (10)	0.0253 (10)	−0.0007 (11)	0.0009 (10)	−0.0013 (8)
C5	0.0330 (13)	0.0335 (14)	0.0269 (13)	−0.0134 (11)	−0.0020 (11)	−0.0001 (11)
C5'	0.0408 (14)	0.0318 (12)	0.0301 (12)	0.0032 (15)	−0.0019 (12)	−0.0073 (10)
C6	0.0188 (11)	0.0378 (15)	0.0209 (12)	−0.0013 (11)	−0.0013 (10)	0.0032 (11)
C6'	0.0471 (16)	0.0316 (12)	0.0262 (11)	0.0036 (16)	−0.0009 (11)	0.0058 (10)
C7	0.0210 (12)	0.0201 (11)	0.0220 (11)	0.0000 (9)	0.0009 (9)	−0.0002 (9)
C8	0.0374 (13)	0.0193 (10)	0.0267 (11)	0.0026 (12)	0.0015 (11)	0.0026 (8)
C9	0.0214 (12)	0.0346 (15)	0.0419 (16)	0.0020 (11)	0.0012 (12)	0.0022 (13)
C10	0.0341 (14)	0.0289 (12)	0.0236 (12)	0.0021 (11)	0.0076 (11)	−0.0003 (9)
N3'	0.0277 (11)	0.0270 (9)	0.0199 (9)	−0.0001 (10)	0.0000 (9)	0.0001 (7)
N11	0.0361 (12)	0.0263 (9)	0.0183 (9)	−0.0012 (11)	−0.0007 (9)	0.0012 (7)
N12	0.0307 (10)	0.0248 (9)	0.0178 (8)	−0.0015 (10)	−0.0019 (9)	0.0010 (7)
O7'	0.0769 (16)	0.0560 (11)	0.0197 (9)	0.0084 (14)	−0.0040 (11)	−0.0025 (8)
S1'	0.0284 (3)	0.0243 (3)	0.0263 (3)	0.0016 (3)	−0.0020 (3)	−0.0004 (2)

Geometric parameters (Å, º)

C1—C2	1.512 (3)	C5'—S1'	1.814 (2)
C1—C8	1.516 (3)	C5'—H5'1	0.9900
C1—C6	1.549 (3)	C5'—H5'2	0.9900
C1—C7	1.556 (3)	C6—H6A	0.9900
C2—N12	1.277 (3)	C6—H6B	0.9900
C2—C3	1.512 (3)	C6'—N3'	1.457 (3)
C2'—N11	1.278 (3)	C6'—H6'1	0.9800
C2'—N3'	1.379 (3)	C6'—H6'2	0.9800
C2'—S1'	1.756 (2)	C6'—H6'3	0.9800
C3—C4	1.541 (3)	C7—C10	1.528 (3)
C3—H3A	0.9900	C7—C9	1.529 (3)
C3—H3B	0.9900	C8—H8A	0.9800
C4'—O7'	1.208 (3)	C8—H8B	0.9800
C4'—N3'	1.373 (3)	C8—H8C	0.9800
C4'—C5'	1.508 (3)	C9—H9A	0.9800
C4—C5	1.538 (3)	C9—H9B	0.9800
C4—C7	1.548 (3)	C9—H9C	0.9800
C4—H4	1.0000	C10—H10A	0.9800
C5—C6	1.540 (4)	C10—H10B	0.9800
C5—H5A	0.9900	C10—H10C	0.9800
C5—H5B	0.9900	N11—N12	1.420 (2)
C2—C1—C8	115.33 (18)	C1—C6—H6A	110.9
C2—C1—C6	103.37 (18)	C5—C6—H6B	110.9
C8—C1—C6	114.9 (2)	C1—C6—H6B	110.9
C2—C1—C7	100.37 (17)	H6A—C6—H6B	108.9
C8—C1—C7	118.72 (19)	N3'—C6'—H6'1	109.5
C6—C1—C7	101.82 (18)	N3'—C6'—H6'2	109.5
N12—C2—C3	130.28 (19)	H6'1—C6'—H6'2	109.5
N12—C2—C1	121.99 (19)	N3'—C6'—H6'3	109.5
C3—C2—C1	107.72 (17)	H6'1—C6'—H6'3	109.5
N11—C2'—N3'	121.08 (19)	H6'2—C6'—H6'3	109.5
N11—C2'—S1'	126.48 (17)	C10—C7—C9	108.1 (2)
N3'—C2'—S1'	112.43 (16)	C10—C7—C4	113.78 (19)
C2—C3—C4	100.87 (16)	C9—C7—C4	113.8 (2)
C2—C3—H3A	111.6	C10—C7—C1	114.45 (18)
C4—C3—H3A	111.6	C9—C7—C1	112.6 (2)
C2—C3—H3B	111.6	C4—C7—C1	93.67 (17)
C4—C3—H3B	111.6	C1—C8—H8A	109.5
H3A—C3—H3B	109.4	C1—C8—H8B	109.5
O7'—C4'—N3'	124.3 (2)	H8A—C8—H8B	109.5
O7'—C4'—C5'	124.6 (2)	C1—C8—H8C	109.5
N3'—C4'—C5'	111.08 (19)	H8A—C8—H8C	109.5
C5—C4—C3	106.02 (19)	H8B—C8—H8C	109.5
C5—C4—C7	102.76 (18)	C7—C9—H9A	109.5
C3—C4—C7	103.12 (17)	C7—C9—H9B	109.5
C5—C4—H4	114.5	H9A—C9—H9B	109.5
C3—C4—H4	114.5	C7—C9—H9C	109.5
C7—C4—H4	114.5	H9A—C9—H9C	109.5
C4—C5—C6	102.68 (19)	H9B—C9—H9C	109.5
C4—C5—H5A	111.2	C7—C10—H10A	109.5
C6—C5—H5A	111.2	C7—C10—H10B	109.5
C4—C5—H5B	111.2	H10A—C10—H10B	109.5
C6—C5—H5B	111.2	C7—C10—H10C	109.5
H5A—C5—H5B	109.1	H10A—C10—H10C	109.5
C4'—C5'—S1'	108.50 (16)	H10B—C10—H10C	109.5
C4'—C5'—H5'1	110.0	C4'—N3'—C2'	116.97 (19)
S1'—C5'—H5'1	110.0	C4'—N3'—C6'	122.63 (19)
C4'—C5'—H5'2	110.0	C2'—N3'—C6'	120.38 (18)
S1'—C5'—H5'2	110.0	C2'—N11—N12	109.14 (17)
H5'1—C5'—H5'2	108.4	C2—N12—N11	113.21 (17)
C5—C6—C1	104.45 (19)	C2'—S1'—C5'	90.99 (11)
C5—C6—H6A	110.9
C2'—N11—N12—C2	177.9 (2)

(2Z,5Z)-5-[(Dimethylamino)methylidene]-2-{(E)-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene]hydrazinylidene}thiazolidin-4-one (3)

Crystal data

C16H24N4OS	Dx = 1.226 Mg m^−3
Mr = 320.45	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 9991 reflections
a = 11.4988 (8) Å	θ = 2.4–28.6°
b = 13.5379 (11) Å	µ = 0.19 mm^−1
c = 22.3107 (16) Å	T = 173 K
V = 3473.1 (4) Å^3	Box, colourless
Z = 8	0.50 × 0.20 × 0.13 mm
F(000) = 1376

Data collection

Bruker APEXII CCD diffractometer	9022 independent reflections
Radiation source: fine-focus sealed tube	7693 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 28.8°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2015)	h = −13→15
Tmin = 0.708, Tmax = 0.746	k = −18→18
39147 measured reflections	l = −30→30

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[σ^2(Fo^2) + (0.0485P)^2 + 0.6983P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.099	(Δ/σ)max = 0.002
S = 1.03	Δρmax = 0.28 e Å^−3
9022 reflections	Δρmin = −0.21 e Å^−3
413 parameters	Absolute structure: Flack x determined using 2988 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: 0.00 (2)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 1.0Å (methine), 0.99Å(methylene), 0.95Å (aromatic) with U_iso(H) = 1.2U_eq(C) and 0.98Å (methyl) with U_iso(H) = 1.2U_eq(C). The coordinates of the H atoms attached to nitrogen were freely refined with U_iso(H) = 1.2U_eq(N)

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

	x	y	z	Uiso*/Ueq
S1'A	1.08659 (5)	0.70562 (4)	0.83031 (2)	0.02920 (13)
O1A	0.84868 (16)	0.66875 (14)	0.70992 (8)	0.0382 (4)
N11A	0.9274 (2)	0.81791 (16)	0.89028 (9)	0.0351 (5)
N12A	1.01999 (19)	0.81605 (16)	0.93186 (9)	0.0335 (5)
N3'A	0.87648 (19)	0.75051 (16)	0.79816 (9)	0.0328 (5)
H3'A	0.804 (3)	0.777 (2)	0.7990 (13)	0.039*
N52A	1.1905 (2)	0.56671 (16)	0.71302 (9)	0.0357 (5)
C2'A	0.9536 (2)	0.76653 (18)	0.84416 (10)	0.0292 (5)
C4'A	0.9131 (2)	0.69016 (18)	0.75243 (9)	0.0301 (5)
C5'A	1.0313 (2)	0.65877 (18)	0.76165 (10)	0.0289 (5)
C51A	1.0848 (2)	0.60552 (17)	0.71755 (10)	0.0315 (5)
H51A	1.037150	0.594034	0.683480	0.038*
C53A	1.2765 (2)	0.5692 (2)	0.76051 (12)	0.0427 (6)
H53A	1.335114	0.619528	0.751369	0.064*
H53B	1.314078	0.504459	0.763711	0.064*
H53C	1.238363	0.585319	0.798567	0.064*
C54A	1.2309 (3)	0.5277 (2)	0.65554 (12)	0.0434 (7)
H54A	1.164824	0.521714	0.628008	0.065*
H54B	1.266033	0.462533	0.661692	0.065*
H54C	1.288779	0.572659	0.638405	0.065*
C1A	1.0720 (2)	0.84707 (18)	1.03649 (10)	0.0304 (5)
C2A	0.9924 (2)	0.85193 (17)	0.98259 (10)	0.0272 (5)
C3A	0.8795 (2)	0.8975 (2)	1.00306 (10)	0.0336 (6)
H3A1	0.812735	0.853044	0.995536	0.040*
H3A2	0.865335	0.961889	0.983370	0.040*
C4A	0.9031 (2)	0.90982 (19)	1.07083 (10)	0.0344 (5)
H4A	0.850226	0.957642	1.091392	0.041*
C5A	0.9033 (3)	0.8066 (2)	1.09801 (11)	0.0479 (7)
H5A1	0.835270	0.767850	1.084354	0.057*
H5A2	0.903323	0.809411	1.142349	0.057*
C6A	1.0179 (3)	0.7623 (2)	1.07398 (11)	0.0456 (7)
H6A1	1.002621	0.703604	1.048682	0.055*
H6A2	1.070037	0.743025	1.107322	0.055*
C7A	1.0323 (2)	0.93912 (18)	1.07211 (10)	0.0298 (5)
C8A	1.1990 (3)	0.8366 (3)	1.02210 (14)	0.0576 (9)
H8A1	1.210700	0.778393	0.996688	0.086*
H8A2	1.243193	0.828857	1.059354	0.086*
H8A3	1.225891	0.895696	1.000868	0.086*
C9A	1.0578 (3)	1.0365 (2)	1.04000 (13)	0.0472 (7)
H9A1	1.010187	1.089141	1.057507	0.071*
H9A2	1.039207	1.029740	0.997321	0.071*
H9A3	1.140285	1.052964	1.044572	0.071*
C10A	1.0831 (3)	0.9443 (2)	1.13555 (11)	0.0431 (6)
H10A	1.166916	0.956680	1.133195	0.065*
H10B	1.069211	0.881549	1.156238	0.065*
H10C	1.045554	0.998013	1.157765	0.065*
S1'B	0.40653 (6)	0.77974 (4)	0.67351 (2)	0.03167 (14)
O1B	0.64583 (16)	0.81736 (14)	0.79305 (8)	0.0385 (4)
N11B	0.5684 (2)	0.67568 (18)	0.61071 (9)	0.0413 (6)
N12B	0.4705 (2)	0.66612 (18)	0.57229 (9)	0.0410 (5)
N3'B	0.6207 (2)	0.74248 (17)	0.70242 (9)	0.0354 (5)
H3'B	0.695 (3)	0.718 (2)	0.7034 (13)	0.042*
N52B	0.3027 (2)	0.91422 (16)	0.79228 (10)	0.0369 (5)
C2'B	0.5417 (2)	0.7247 (2)	0.65725 (10)	0.0329 (5)
C4'B	0.5823 (2)	0.79727 (18)	0.75012 (9)	0.0305 (5)
C5'B	0.4623 (2)	0.82584 (18)	0.74221 (10)	0.0293 (5)
C51B	0.4090 (2)	0.87789 (17)	0.78691 (10)	0.0313 (5)
H51B	0.457471	0.890375	0.820543	0.038*
C53B	0.2159 (2)	0.9115 (2)	0.74494 (11)	0.0405 (6)
H53D	0.254062	0.919905	0.706006	0.061*
H53E	0.159664	0.965029	0.751043	0.061*
H53F	0.175322	0.847880	0.745858	0.061*
C54B	0.2648 (3)	0.9568 (2)	0.84936 (12)	0.0473 (7)
H54D	0.332332	0.966307	0.875514	0.071*
H54E	0.209377	0.912057	0.868749	0.071*
H54F	0.227235	1.020704	0.842024	0.071*
C1B	0.4138 (2)	0.60855 (18)	0.47219 (10)	0.0325 (5)
C2B	0.4995 (2)	0.63107 (18)	0.52138 (10)	0.0292 (5)
C3B	0.6185 (2)	0.6022 (2)	0.49946 (10)	0.0330 (6)
H3B1	0.653852	0.550745	0.525174	0.040*
H3B2	0.671201	0.659889	0.497250	0.040*
C4B	0.5893 (2)	0.5622 (2)	0.43705 (11)	0.0382 (6)
H4B	0.656872	0.559107	0.408908	0.046*
C5B	0.5282 (2)	0.4636 (2)	0.44726 (15)	0.0493 (7)
H5B1	0.570578	0.422987	0.477009	0.059*
H5B2	0.521238	0.425995	0.409380	0.059*
C6B	0.4080 (2)	0.49411 (19)	0.47107 (14)	0.0428 (6)
H6B1	0.394461	0.467236	0.511745	0.051*
H6B2	0.345319	0.470834	0.444104	0.051*
C7B	0.4900 (2)	0.6300 (2)	0.41649 (10)	0.0360 (6)
C8B	0.2974 (3)	0.6591 (3)	0.47758 (15)	0.0538 (8)
H8B1	0.260391	0.639809	0.515370	0.081*
H8B2	0.247741	0.639514	0.443938	0.081*
H8B3	0.308543	0.730874	0.476953	0.081*
C9B	0.5251 (3)	0.7389 (3)	0.41185 (16)	0.0642 (10)
H9B1	0.588167	0.745985	0.382598	0.096*
H9B2	0.551652	0.762390	0.451095	0.096*
H9B3	0.458018	0.778119	0.398891	0.096*
C10B	0.4338 (3)	0.5985 (3)	0.35703 (12)	0.0556 (8)
H10D	0.362471	0.636618	0.350543	0.083*
H10E	0.414902	0.527924	0.358602	0.083*
H10F	0.488142	0.610730	0.324024	0.083*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1'A	0.0348 (3)	0.0323 (3)	0.0205 (2)	−0.0024 (2)	−0.0035 (2)	0.0006 (2)
O1A	0.0358 (10)	0.0510 (11)	0.0277 (9)	−0.0020 (8)	−0.0051 (8)	−0.0115 (8)
N11A	0.0415 (12)	0.0413 (12)	0.0225 (9)	0.0042 (10)	−0.0064 (9)	−0.0035 (8)
N12A	0.0367 (12)	0.0394 (12)	0.0244 (9)	0.0059 (9)	−0.0054 (8)	−0.0059 (8)
N3'A	0.0356 (12)	0.0412 (12)	0.0215 (9)	0.0023 (9)	−0.0049 (9)	−0.0062 (8)
N52A	0.0400 (12)	0.0378 (12)	0.0293 (10)	0.0028 (9)	0.0002 (9)	−0.0033 (9)
C2'A	0.0364 (13)	0.0301 (12)	0.0211 (10)	−0.0019 (10)	−0.0018 (9)	0.0011 (9)
C4'A	0.0348 (12)	0.0343 (12)	0.0214 (10)	−0.0052 (11)	0.0000 (10)	−0.0012 (8)
C5'A	0.0370 (13)	0.0299 (12)	0.0197 (10)	−0.0049 (10)	−0.0023 (9)	0.0007 (9)
C51A	0.0385 (13)	0.0308 (11)	0.0253 (10)	−0.0050 (11)	−0.0020 (11)	0.0020 (9)
C53A	0.0400 (15)	0.0523 (17)	0.0357 (13)	0.0044 (13)	−0.0013 (12)	0.0018 (12)
C54A	0.0496 (16)	0.0436 (16)	0.0372 (15)	0.0065 (13)	0.0030 (12)	−0.0094 (12)
C1A	0.0331 (13)	0.0363 (12)	0.0218 (10)	0.0068 (10)	−0.0066 (9)	−0.0053 (9)
C2A	0.0319 (13)	0.0263 (11)	0.0233 (10)	−0.0004 (9)	−0.0057 (9)	−0.0015 (9)
C3A	0.0281 (14)	0.0464 (14)	0.0263 (12)	−0.0001 (11)	−0.0033 (10)	−0.0048 (10)
C4A	0.0310 (13)	0.0471 (14)	0.0252 (11)	0.0006 (12)	0.0005 (10)	−0.0089 (10)
C5A	0.0562 (18)	0.0584 (17)	0.0292 (12)	−0.0237 (16)	−0.0017 (12)	0.0027 (11)
C6A	0.077 (2)	0.0292 (14)	0.0300 (13)	−0.0013 (13)	−0.0172 (14)	−0.0014 (10)
C7A	0.0319 (12)	0.0309 (12)	0.0266 (11)	−0.0029 (10)	−0.0052 (9)	−0.0048 (9)
C8A	0.0391 (17)	0.091 (3)	0.0424 (16)	0.0225 (17)	−0.0087 (14)	−0.0122 (17)
C9A	0.0584 (19)	0.0387 (15)	0.0444 (16)	−0.0126 (13)	−0.0112 (14)	−0.0006 (12)
C10A	0.0528 (17)	0.0446 (15)	0.0320 (12)	−0.0036 (14)	−0.0131 (12)	−0.0097 (11)
S1'B	0.0363 (3)	0.0342 (3)	0.0245 (3)	−0.0002 (3)	−0.0040 (3)	−0.0021 (2)
O1B	0.0377 (10)	0.0513 (11)	0.0266 (8)	−0.0007 (8)	−0.0039 (8)	−0.0105 (8)
N11B	0.0394 (13)	0.0574 (14)	0.0271 (10)	0.0077 (11)	−0.0074 (10)	−0.0121 (10)
N12B	0.0395 (12)	0.0559 (15)	0.0276 (10)	0.0081 (11)	−0.0047 (9)	−0.0099 (10)
N3'B	0.0342 (12)	0.0468 (13)	0.0252 (10)	0.0028 (10)	−0.0025 (9)	−0.0066 (9)
N52B	0.0416 (13)	0.0389 (12)	0.0302 (10)	0.0001 (10)	0.0023 (9)	−0.0046 (9)
C2'B	0.0361 (13)	0.0394 (13)	0.0232 (11)	0.0004 (11)	−0.0007 (10)	−0.0016 (10)
C4'B	0.0366 (13)	0.0325 (12)	0.0224 (10)	−0.0056 (11)	−0.0004 (10)	0.0006 (8)
C5'B	0.0364 (13)	0.0298 (12)	0.0216 (10)	−0.0053 (10)	−0.0027 (10)	0.0006 (9)
C51B	0.0384 (13)	0.0290 (11)	0.0267 (11)	−0.0034 (11)	−0.0023 (11)	0.0006 (9)
C53B	0.0374 (14)	0.0482 (16)	0.0360 (14)	0.0020 (12)	−0.0017 (11)	0.0053 (12)
C54B	0.0535 (18)	0.0491 (17)	0.0391 (15)	0.0078 (15)	0.0051 (13)	−0.0113 (13)
C1B	0.0275 (12)	0.0402 (13)	0.0297 (11)	0.0040 (11)	−0.0048 (10)	−0.0059 (10)
C2B	0.0294 (13)	0.0327 (12)	0.0256 (11)	−0.0003 (10)	−0.0012 (10)	−0.0047 (9)
C3B	0.0283 (14)	0.0404 (14)	0.0302 (12)	−0.0037 (10)	−0.0038 (10)	−0.0067 (10)
C4B	0.0277 (12)	0.0556 (16)	0.0312 (12)	0.0002 (12)	0.0012 (11)	−0.0142 (11)
C5B	0.0398 (15)	0.0415 (16)	0.0666 (19)	0.0059 (13)	−0.0185 (14)	−0.0179 (14)
C6B	0.0338 (14)	0.0387 (14)	0.0559 (17)	−0.0102 (12)	−0.0122 (13)	0.0010 (12)
C7B	0.0421 (14)	0.0411 (14)	0.0248 (11)	−0.0029 (11)	−0.0051 (10)	−0.0029 (10)
C8B	0.0373 (17)	0.071 (2)	0.0535 (18)	0.0205 (15)	−0.0095 (14)	−0.0135 (16)
C9B	0.079 (2)	0.055 (2)	0.058 (2)	−0.0194 (18)	−0.0142 (18)	0.0209 (16)
C10B	0.058 (2)	0.080 (2)	0.0288 (13)	0.0059 (17)	−0.0116 (13)	−0.0105 (14)

Geometric parameters (Å, º)

S1'A—C2'A	1.765 (3)	S1'B—C2'B	1.762 (3)
S1'A—C5'A	1.776 (2)	S1'B—C5'B	1.775 (2)
O1A—C4'A	1.238 (3)	O1B—C4'B	1.235 (3)
N11A—C2'A	1.278 (3)	N11B—C2'B	1.270 (3)
N11A—N12A	1.412 (3)	N11B—N12B	1.421 (3)
N12A—C2A	1.272 (3)	N12B—C2B	1.275 (3)
N3'A—C4'A	1.373 (3)	N3'B—C4'B	1.370 (3)
N3'A—C2'A	1.373 (3)	N3'B—C2'B	1.377 (3)
N3'A—H3'A	0.91 (3)	N3'B—H3'B	0.92 (3)
N52A—C51A	1.327 (3)	N52B—C51B	1.323 (4)
N52A—C53A	1.450 (3)	N52B—C53B	1.454 (3)
N52A—C54A	1.463 (3)	N52B—C54B	1.464 (3)
C4'A—C5'A	1.439 (4)	C4'B—C5'B	1.444 (4)
C5'A—C51A	1.366 (3)	C5'B—C51B	1.366 (3)
C51A—H51A	0.9500	C51B—H51B	0.9500
C53A—H53A	0.9800	C53B—H53D	0.9800
C53A—H53B	0.9800	C53B—H53E	0.9800
C53A—H53C	0.9800	C53B—H53F	0.9800
C54A—H54A	0.9800	C54B—H54D	0.9800
C54A—H54B	0.9800	C54B—H54E	0.9800
C54A—H54C	0.9800	C54B—H54F	0.9800
C1A—C8A	1.502 (4)	C1B—C2B	1.506 (3)
C1A—C2A	1.513 (3)	C1B—C8B	1.507 (4)
C1A—C7A	1.547 (3)	C1B—C7B	1.549 (4)
C1A—C6A	1.550 (4)	C1B—C6B	1.551 (3)
C2A—C3A	1.507 (4)	C2B—C3B	1.504 (4)
C3A—C4A	1.545 (3)	C3B—C4B	1.531 (3)
C3A—H3A1	0.9900	C3B—H3B1	0.9900
C3A—H3A2	0.9900	C3B—H3B2	0.9900
C4A—C5A	1.524 (4)	C4B—C5B	1.525 (4)
C4A—C7A	1.537 (3)	C4B—C7B	1.535 (4)
C4A—H4A	1.0000	C4B—H4B	1.0000
C5A—C6A	1.544 (4)	C5B—C6B	1.538 (4)
C5A—H5A1	0.9900	C5B—H5B1	0.9900
C5A—H5A2	0.9900	C5B—H5B2	0.9900
C6A—H6A1	0.9900	C6B—H6B1	0.9900
C6A—H6A2	0.9900	C6B—H6B2	0.9900
C7A—C9A	1.528 (4)	C7B—C9B	1.532 (4)
C7A—C10A	1.533 (3)	C7B—C10B	1.536 (3)
C8A—H8A1	0.9800	C8B—H8B1	0.9800
C8A—H8A2	0.9800	C8B—H8B2	0.9800
C8A—H8A3	0.9800	C8B—H8B3	0.9800
C9A—H9A1	0.9800	C9B—H9B1	0.9800
C9A—H9A2	0.9800	C9B—H9B2	0.9800
C9A—H9A3	0.9800	C9B—H9B3	0.9800
C10A—H10A	0.9800	C10B—H10D	0.9800
C10A—H10B	0.9800	C10B—H10E	0.9800
C10A—H10C	0.9800	C10B—H10F	0.9800
C2'A—S1'A—C5'A	90.44 (12)	C2'B—S1'B—C5'B	90.44 (12)
C2'A—N11A—N12A	110.0 (2)	C2'B—N11B—N12B	110.5 (2)
C2A—N12A—N11A	112.9 (2)	C2B—N12B—N11B	111.3 (2)
C4'A—N3'A—C2'A	116.8 (2)	C4'B—N3'B—C2'B	116.8 (2)
C4'A—N3'A—H3'A	122.3 (18)	C4'B—N3'B—H3'B	118.3 (19)
C2'A—N3'A—H3'A	120.9 (18)	C2'B—N3'B—H3'B	124.9 (19)
C51A—N52A—C53A	124.0 (2)	C51B—N52B—C53B	124.0 (2)
C51A—N52A—C54A	120.0 (2)	C51B—N52B—C54B	120.0 (2)
C53A—N52A—C54A	115.6 (2)	C53B—N52B—C54B	115.9 (2)
N11A—C2'A—N3'A	122.4 (2)	N11B—C2'B—N3'B	122.0 (2)
N11A—C2'A—S1'A	126.82 (19)	N11B—C2'B—S1'B	127.0 (2)
N3'A—C2'A—S1'A	110.78 (17)	N3'B—C2'B—S1'B	110.91 (17)
O1A—C4'A—N3'A	121.7 (2)	O1B—C4'B—N3'B	122.1 (2)
O1A—C4'A—C5'A	127.3 (2)	O1B—C4'B—C5'B	127.0 (2)
N3'A—C4'A—C5'A	111.1 (2)	N3'B—C4'B—C5'B	111.0 (2)
C51A—C5'A—C4'A	118.6 (2)	C51B—C5'B—C4'B	118.5 (2)
C51A—C5'A—S1'A	130.4 (2)	C51B—C5'B—S1'B	130.5 (2)
C4'A—C5'A—S1'A	110.85 (17)	C4'B—C5'B—S1'B	110.89 (17)
N52A—C51A—C5'A	132.5 (2)	N52B—C51B—C5'B	132.3 (2)
N52A—C51A—H51A	113.7	N52B—C51B—H51B	113.9
C5'A—C51A—H51A	113.7	C5'B—C51B—H51B	113.9
N52A—C53A—H53A	109.5	N52B—C53B—H53D	109.5
N52A—C53A—H53B	109.5	N52B—C53B—H53E	109.5
H53A—C53A—H53B	109.5	H53D—C53B—H53E	109.5
N52A—C53A—H53C	109.5	N52B—C53B—H53F	109.5
H53A—C53A—H53C	109.5	H53D—C53B—H53F	109.5
H53B—C53A—H53C	109.5	H53E—C53B—H53F	109.5
N52A—C54A—H54A	109.5	N52B—C54B—H54D	109.5
N52A—C54A—H54B	109.5	N52B—C54B—H54E	109.5
H54A—C54A—H54B	109.5	H54D—C54B—H54E	109.5
N52A—C54A—H54C	109.5	N52B—C54B—H54F	109.5
H54A—C54A—H54C	109.5	H54D—C54B—H54F	109.5
H54B—C54A—H54C	109.5	H54E—C54B—H54F	109.5
C8A—C1A—C2A	115.0 (2)	C2B—C1B—C8B	115.5 (2)
C8A—C1A—C7A	118.2 (2)	C2B—C1B—C7B	100.14 (19)
C2A—C1A—C7A	101.23 (19)	C8B—C1B—C7B	118.8 (2)
C8A—C1A—C6A	115.8 (2)	C2B—C1B—C6B	104.0 (2)
C2A—C1A—C6A	102.6 (2)	C8B—C1B—C6B	114.6 (3)
C7A—C1A—C6A	101.60 (19)	C7B—C1B—C6B	101.5 (2)
N12A—C2A—C3A	129.9 (2)	N12B—C2B—C3B	128.6 (2)
N12A—C2A—C1A	122.7 (2)	N12B—C2B—C1B	123.6 (2)
C3A—C2A—C1A	107.32 (19)	C3B—C2B—C1B	107.80 (19)
C2A—C3A—C4A	100.93 (19)	C2B—C3B—C4B	100.9 (2)
C2A—C3A—H3A1	111.6	C2B—C3B—H3B1	111.6
C4A—C3A—H3A1	111.6	C4B—C3B—H3B1	111.6
C2A—C3A—H3A2	111.6	C2B—C3B—H3B2	111.6
C4A—C3A—H3A2	111.6	C4B—C3B—H3B2	111.6
H3A1—C3A—H3A2	109.4	H3B1—C3B—H3B2	109.4
C5A—C4A—C7A	103.2 (2)	C5B—C4B—C3B	105.9 (2)
C5A—C4A—C3A	106.9 (2)	C5B—C4B—C7B	103.1 (2)
C7A—C4A—C3A	102.46 (19)	C3B—C4B—C7B	102.9 (2)
C5A—C4A—H4A	114.3	C5B—C4B—H4B	114.5
C7A—C4A—H4A	114.3	C3B—C4B—H4B	114.5
C3A—C4A—H4A	114.3	C7B—C4B—H4B	114.5
C4A—C5A—C6A	102.7 (2)	C4B—C5B—C6B	103.3 (2)
C4A—C5A—H5A1	111.2	C4B—C5B—H5B1	111.1
C6A—C5A—H5A1	111.2	C6B—C5B—H5B1	111.1
C4A—C5A—H5A2	111.2	C4B—C5B—H5B2	111.1
C6A—C5A—H5A2	111.2	C6B—C5B—H5B2	111.1
H5A1—C5A—H5A2	109.1	H5B1—C5B—H5B2	109.1
C5A—C6A—C1A	104.0 (2)	C5B—C6B—C1B	103.6 (2)
C5A—C6A—H6A1	111.0	C5B—C6B—H6B1	111.0
C1A—C6A—H6A1	111.0	C1B—C6B—H6B1	111.0
C5A—C6A—H6A2	111.0	C5B—C6B—H6B2	111.0
C1A—C6A—H6A2	111.0	C1B—C6B—H6B2	111.0
H6A1—C6A—H6A2	109.0	H6B1—C6B—H6B2	109.0
C9A—C7A—C10A	108.7 (2)	C9B—C7B—C4B	113.6 (2)
C9A—C7A—C4A	113.5 (2)	C9B—C7B—C10B	108.7 (2)
C10A—C7A—C4A	113.4 (2)	C4B—C7B—C10B	113.9 (2)
C9A—C7A—C1A	113.4 (2)	C9B—C7B—C1B	112.6 (2)
C10A—C7A—C1A	113.5 (2)	C4B—C7B—C1B	93.96 (19)
C4A—C7A—C1A	93.87 (18)	C10B—C7B—C1B	113.7 (2)
C1A—C8A—H8A1	109.5	C1B—C8B—H8B1	109.5
C1A—C8A—H8A2	109.5	C1B—C8B—H8B2	109.5
H8A1—C8A—H8A2	109.5	H8B1—C8B—H8B2	109.5
C1A—C8A—H8A3	109.5	C1B—C8B—H8B3	109.5
H8A1—C8A—H8A3	109.5	H8B1—C8B—H8B3	109.5
H8A2—C8A—H8A3	109.5	H8B2—C8B—H8B3	109.5
C7A—C9A—H9A1	109.5	C7B—C9B—H9B1	109.5
C7A—C9A—H9A2	109.5	C7B—C9B—H9B2	109.5
H9A1—C9A—H9A2	109.5	H9B1—C9B—H9B2	109.5
C7A—C9A—H9A3	109.5	C7B—C9B—H9B3	109.5
H9A1—C9A—H9A3	109.5	H9B1—C9B—H9B3	109.5
H9A2—C9A—H9A3	109.5	H9B2—C9B—H9B3	109.5
C7A—C10A—H10A	109.5	C7B—C10B—H10D	109.5
C7A—C10A—H10B	109.5	C7B—C10B—H10E	109.5
H10A—C10A—H10B	109.5	H10D—C10B—H10E	109.5
C7A—C10A—H10C	109.5	C7B—C10B—H10F	109.5
H10A—C10A—H10C	109.5	H10D—C10B—H10F	109.5
H10B—C10A—H10C	109.5	H10E—C10B—H10F	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3′A—H3′A···O1B	0.91 (3)	1.90 (3)	2.805 (3)	171 (3)
C53A—H53A···S1′B^i	0.98	2.90	3.759 (3)	147
C53A—H53C···S1′A	0.98	2.49	3.256 (3)	135
C54A—H54B···O1B^ii	0.98	2.43	3.381 (3)	163
N3′B—H3′B···O1A	0.92 (3)	1.89 (3)	2.810 (3)	177 (3)
C53B—H53D···S1′B	0.98	2.68	3.245 (3)	117
C53B—H53F···S1′A^iii	0.98	2.88	3.689 (3)	140
C54B—H54F···O1A^iv	0.98	2.47	3.418 (4)	162

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