2,3,5,6-Tetra­kis(phenoxy­methyl)­pyrazine and 2,3,5,6-tetrakis(phenyl­sulfanyl­methyl)pyrazine

The title compounds, C₃₂H₂₈N₂O₄, (I), and C₃₂H₂₈N₂S₄, (II), respectively, are tetra­substituted pyrazines and both possess C_i symmetry. They differ only in the hetero atom (X) of the –­CH₂XPh side-arm substituents: X = O in (I) and S in (II). Compound (I) has an overall S-shape with a pair of adjacent –­CH₂OPh side arms alternately above and below the plane of the central pyrazine ring. The phenyl rings are inclined to one another by 12.63 (18)° and there is one intra­molecular C—H...O hydrogen bond involving adjacent –CH₂OPh side arms. In compound (II), adjacent –CH₂SPh side arms point in opposite directions with respect to the pyrazine ring plane, with the phenyl rings inclined at 60.45 (8)°. Both structures have weak C—H...π inter­molecular inter­actions.

Computing details

Data collection: STADI4 (Stoe & Cie, 1997) for (I); X-AREA (Stoe & Cie, 2006) for (II). Cell refinement: STADI4 for (I); X-AREA for (II). Data reduction: X-RED (Stoe & Cie, 1997) for (I); X-RED32 (Stoe & Cie, 2006) for (II). For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97.

(I) 2,3,5,6-tetrakis(phenoxymethyl)pyrazine

Crystal data

C32H28N2O4	F(000) = 532
Mr = 504.56	Dx = 1.301 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 96 reflections
a = 12.4717 (15) Å	θ = 10.0–16.8°
b = 5.0859 (6) Å	µ = 0.09 mm^−1
c = 21.0412 (19) Å	T = 223 K
β = 105.243 (11)°	Plate, colourless
V = 1287.7 (2) Å^3	0.49 × 0.46 × 0.11 mm
Z = 2

Data collection

Stoe AED2 four-circle diffractometer	Rint = 0.053
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 2.0°
Graphite monochromator	h = −15→15
2θ/ω scans	k = 0→6
4618 measured reflections	l = −25→25
2391 independent reflections	2 standard reflections every 60 min
1373 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.150	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0482P)^2 + 0.4352P] where P = (Fo^2 + 2Fc^2)/3
2391 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

Experimental. IR (KBr disc, ν, cm^-1): 3855 (w), 3752 (w), 3439 (m, b), 3065 (w), 3041 (w), 3030 (w), 2951 (w), 2892 (w), 2853 (w), 2452 (w), 2366 (w), 2027 (w), 1941 (w), 1852 (w), 1775 (w), 1708 (w), 1600 (s), 1587 (w), 1495 (s), 1459 (m), 1435 (m), 1415 (w), 1368 (m), 1354 (w), 1337 (w), 1303 (m), 1294 (m), 1234 (s), 1218 (s), 1184 (m), 1175 (m), 1163 (m), 1080 (m), 1048 (m), 1036 (m), 1019 (m), 1001 (m), 991 (m), 967 (w), 876 (m), 782 (m), 774 (m), 752 (s), 689 (s), 646 (w), 598 (w), 555 (w), 523 (w), 507 (w), 484 (w), 449 (w), 424 (w), 410 (w); ¹H NMR (CDCl₃, 400 MHz, δ, p.p.m.): 7.27 (dd, 8H, 3 J = 7.35 Hz, 3 J = 8.78 Hz, Hphe), 7.03 (dd, 4H, 3 J = 8.78 Hz, 4 J = 0.97 Hz, Hphe), 6.95 (dd, 8H, 3 J = 7.35 Hz, 4 J = 0.97 Hz, Hphe), 5.48 (s, 8H, CH₂); ¹³C NMR (CDCl₃, 400 MHz, δ, p.p.m.): 159.0 (4 C, Cphe), 150.3 (4 C, Cpyr), 129.8 (8 C, CHphe), 121.5 (4 C, CHphe), 115.2 (8 C, CHphe), 69.4 (4 C, CH₂); CCM (CH₂Cl₂–toluene 10:3 v/v): R_f = 0.40; ESI MS m/z: 527 ([M⁺Na]⁺), 505 ([M⁺H]⁺), 411, 317.

Analytical data for (II)

mp 113–115 °C, Rf 0.45 (solvent: CH₂Cl₂, eluent: toluene/light petroleum, 10/1 v/v). ¹H-RMN (CDCl₃, 400 MHz, p.p.m.): δ = 7.32–7.20 (m, 20 H, PhH); 4.20 (s, 8 H, Pz—CH₂—S). ¹³C-RMN (CDCl₃, 100 MHz, p.p.m.): δ = 149.21, 134.92, 130.78, 128.96, 126.99, 37.51. Anal. for C₃₂H₂₈N₂S₄ (Mr = 568.86 g/mol) Calc. (%): C: 67.56 H: 4.97 N: 4.93 S: 22.54 Found (%): C: 67.43 H: 4.77 N: 4.96 S: 22.75 MS (EI, 70 eV), m/z (%): 569 ([M⁺], 3.9), 459 (25.1), 349 (40.4), 316 (10.5), 241 (33.7), 218 (36.2), 110 (100), 84 (27.6), 77 (39.2), 65 (66.5). IR (KBr disc, cm^-1) 3053 w, 2899 w, 1941 vw, 1858vw, 1793 vw, 1730 vw, 1579 s, 1480 s, 1416 s, 1226 w, 1132 w, 1088 w, 1025 w, 883 w, 819 w, 780 w, 736 versus, 690 versus, 476 ms.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.24912 (17)	0.2411 (5)	0.38375 (9)	0.0487 (8)
O2	0.38796 (16)	0.6564 (4)	0.33248 (9)	0.0409 (7)
N1	0.43911 (19)	0.3634 (5)	0.53577 (11)	0.0374 (8)
C1	0.4187 (2)	0.3323 (6)	0.47038 (13)	0.0346 (9)
C2	0.4800 (2)	0.4702 (6)	0.43447 (13)	0.0345 (9)
C3	0.3288 (2)	0.1373 (6)	0.43972 (15)	0.0441 (11)
C4	0.1767 (2)	0.4313 (7)	0.39368 (16)	0.0435 (11)
C5	0.1587 (3)	0.4969 (8)	0.45317 (18)	0.0627 (14)
C6	0.0810 (3)	0.6900 (10)	0.4551 (2)	0.0874 (18)
C7	0.0233 (3)	0.8153 (10)	0.3990 (3)	0.096 (2)
C8	0.0426 (3)	0.7495 (11)	0.3407 (3)	0.096 (2)
C9	0.1182 (3)	0.5581 (9)	0.33766 (19)	0.0710 (18)
C10	0.4600 (2)	0.4438 (6)	0.36122 (13)	0.0381 (10)
C11	0.3477 (2)	0.6565 (6)	0.26473 (13)	0.0345 (9)
C12	0.2707 (2)	0.8476 (7)	0.23885 (15)	0.0452 (11)
C13	0.2266 (3)	0.8649 (7)	0.17147 (16)	0.0523 (11)
C14	0.2601 (3)	0.6912 (7)	0.13012 (15)	0.0511 (11)
C15	0.3365 (2)	0.5004 (7)	0.15599 (14)	0.0458 (11)
C16	0.3819 (2)	0.4810 (6)	0.22364 (14)	0.0386 (10)
H3A	0.36310	−0.01950	0.42640	0.0530*
H3B	0.29060	0.08330	0.47280	0.0530*
H5	0.19840	0.41260	0.49200	0.0750*
H6	0.06780	0.73540	0.49570	0.1050*
H7	−0.02910	0.94570	0.40100	0.1160*
H8	0.00370	0.83590	0.30200	0.1150*
H9	0.13020	0.51290	0.29680	0.0850*
H10A	0.53030	0.45500	0.34880	0.0460*
H10B	0.42500	0.27440	0.34620	0.0460*
H12	0.24800	0.96650	0.26700	0.0540*
H13	0.17370	0.99520	0.15380	0.0620*
H14	0.23050	0.70390	0.08430	0.0610*
H15	0.35840	0.38100	0.12770	0.0550*
H16	0.43500	0.35100	0.24120	0.0460*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0460 (12)	0.0569 (15)	0.0394 (12)	0.0001 (12)	0.0047 (10)	−0.0113 (12)
O2	0.0501 (12)	0.0420 (13)	0.0285 (11)	0.0127 (11)	0.0065 (9)	−0.0006 (10)
N1	0.0422 (14)	0.0375 (15)	0.0318 (14)	0.0038 (12)	0.0083 (11)	−0.0013 (12)
C1	0.0370 (15)	0.0319 (17)	0.0328 (16)	0.0047 (14)	0.0056 (12)	−0.0032 (14)
C2	0.0400 (15)	0.0330 (17)	0.0297 (15)	0.0092 (15)	0.0078 (13)	−0.0017 (14)
C3	0.0469 (18)	0.0365 (19)	0.0468 (19)	0.0031 (16)	0.0087 (15)	−0.0051 (16)
C4	0.0335 (16)	0.044 (2)	0.051 (2)	−0.0099 (16)	0.0074 (14)	−0.0025 (17)
C5	0.052 (2)	0.074 (3)	0.056 (2)	0.005 (2)	0.0033 (17)	−0.024 (2)
C6	0.051 (2)	0.098 (4)	0.105 (3)	0.005 (3)	0.006 (2)	−0.057 (3)
C7	0.041 (2)	0.066 (3)	0.170 (5)	0.002 (2)	0.006 (3)	−0.016 (4)
C8	0.051 (3)	0.095 (4)	0.135 (5)	0.010 (3)	0.011 (3)	0.053 (4)
C9	0.043 (2)	0.098 (4)	0.069 (3)	−0.003 (2)	0.0092 (18)	0.027 (3)
C10	0.0397 (16)	0.0390 (19)	0.0339 (16)	0.0083 (14)	0.0065 (13)	0.0000 (14)
C11	0.0343 (15)	0.0386 (18)	0.0292 (15)	−0.0040 (14)	0.0057 (12)	0.0003 (14)
C12	0.0491 (18)	0.043 (2)	0.0429 (18)	0.0088 (17)	0.0110 (15)	0.0041 (16)
C13	0.0446 (19)	0.052 (2)	0.055 (2)	0.0054 (18)	0.0038 (16)	0.0151 (19)
C14	0.0524 (19)	0.061 (2)	0.0347 (18)	−0.0099 (19)	0.0024 (15)	0.0075 (18)
C15	0.0550 (19)	0.050 (2)	0.0320 (17)	−0.0047 (18)	0.0106 (14)	−0.0022 (16)
C16	0.0434 (16)	0.0401 (19)	0.0333 (16)	0.0004 (16)	0.0117 (13)	−0.0017 (15)

Geometric parameters (Å, º)

O1—C3	1.428 (4)	C13—C14	1.380 (5)
O1—C4	1.376 (4)	C14—C15	1.369 (5)
O2—C10	1.434 (4)	C15—C16	1.390 (4)
O2—C11	1.381 (3)	C3—H3A	0.9800
N1—C1	1.341 (3)	C3—H3B	0.9800
N1—C2^i	1.339 (4)	C5—H5	0.9400
C1—C2	1.397 (4)	C6—H6	0.9400
C1—C3	1.509 (4)	C7—H7	0.9400
C2—C10	1.501 (4)	C8—H8	0.9400
C4—C5	1.370 (5)	C9—H9	0.9400
C4—C9	1.373 (5)	C10—H10A	0.9800
C5—C6	1.388 (6)	C10—H10B	0.9800
C6—C7	1.368 (7)	C12—H12	0.9400
C7—C8	1.353 (8)	C13—H13	0.9400
C8—C9	1.368 (7)	C14—H14	0.9400
C11—C12	1.374 (4)	C15—H15	0.9400
C11—C16	1.386 (4)	C16—H16	0.9400
C12—C13	1.382 (4)
O1···O2	3.099 (3)	C16···H10B	2.7000
O1···C10	2.977 (3)	C16···H16^vi	2.9000
O2···C4	3.420 (4)	H3A···O2^ii	2.6500
O2···O1	3.099 (3)	H3A···C2^ii	2.9600
O2···N1^i	3.034 (3)	H3A···H10B	2.5200
O1···H12^ii	2.8200	H3B···C5	2.6400
O1···H10B	2.5300	H3B···H5	2.1300
O2···H3A^iii	2.6500	H5···N1	2.9100
N1···O2^i	3.034 (3)	H5···C1	2.9300
N1···N1^i	2.776 (3)	H5···C3	2.6000
N1···H5	2.9100	H5···H3B	2.1300
N1···H15^iv	2.7100	H6···H14^vii	2.3900
C1···C5	3.276 (5)	H7···C14^ix	3.0500
C4···O2	3.420 (4)	H8···H9^ix	2.4700
C5···C1	3.276 (5)	H9···C11	3.0500
C9···C12	3.491 (5)	H9···C12	2.9300
C10···C15^v	3.484 (4)	H9···H8^viii	2.4700
C10···O1	2.977 (3)	H10A···C16	2.8000
C12···C16^iii	3.555 (5)	H10A···H16	2.3200
C12···C9	3.491 (5)	H10A···C14^v	2.8700
C13···C15^iii	3.559 (5)	H10A···C15^v	2.8600
C15···C13^ii	3.559 (5)	H10A···H15^vi	2.5500
C15···C10^vi	3.484 (4)	H10B···O1	2.5300
C16···C12^ii	3.555 (5)	H10B···C3	2.6500
C1···H5	2.9300	H10B···C16	2.7000
C2···H3A^iii	2.9600	H10B···H3A	2.5200
C3···H5	2.6000	H10B···H16	2.2800
C3···H10B	2.6500	H12···O1^iii	2.8200
C5···H14^vii	3.0700	H13···C7^ix	2.9100
C5···H3B	2.6400	H13···C8^ix	3.0200
C6···H14^vii	2.9100	H14···C5^x	3.0700
C7···H13^viii	2.9100	H14···C6^x	2.9100
C8···H13^viii	3.0200	H14···H6^x	2.3900
C10···H16	2.5100	H15···H10A^v	2.5500
C11···H9	3.0500	H15···N1^xi	2.7100
C11···H16^vi	2.9200	H16···C10	2.5100
C12···H9	2.9300	H16···H10A	2.3200
C14···H10A^vi	2.8700	H16···H10B	2.2800
C14···H7^viii	3.0500	H16···C11^v	2.9200
C15···H10A^vi	2.8600	H16···C16^v	2.9000
C16···H10A	2.8000
C3—O1—C4	118.5 (2)	C1—C3—H3A	109.00
C10—O2—C11	116.9 (2)	C1—C3—H3B	109.00
C1—N1—C2^i	118.1 (2)	H3A—C3—H3B	108.00
N1—C1—C2	120.8 (3)	C4—C5—H5	121.00
N1—C1—C3	115.8 (2)	C6—C5—H5	121.00
C2—C1—C3	123.3 (2)	C5—C6—H6	119.00
C1—C2—C10	122.9 (2)	C7—C6—H6	119.00
N1^i—C2—C1	121.1 (2)	C6—C7—H7	120.00
N1^i—C2—C10	116.0 (2)	C8—C7—H7	120.00
O1—C3—C1	112.8 (2)	C7—C8—H8	120.00
O1—C4—C5	125.6 (3)	C9—C8—H8	120.00
O1—C4—C9	114.9 (3)	C4—C9—H9	120.00
C5—C4—C9	119.5 (3)	C8—C9—H9	120.00
C4—C5—C6	118.9 (3)	O2—C10—H10A	110.00
C5—C6—C7	121.2 (4)	O2—C10—H10B	111.00
C6—C7—C8	119.3 (4)	C2—C10—H10A	110.00
C7—C8—C9	120.5 (5)	C2—C10—H10B	110.00
C4—C9—C8	120.7 (4)	H10A—C10—H10B	109.00
O2—C10—C2	106.4 (2)	C11—C12—H12	120.00
O2—C11—C12	115.8 (3)	C13—C12—H12	120.00
O2—C11—C16	123.8 (3)	C12—C13—H13	120.00
C12—C11—C16	120.4 (3)	C14—C13—H13	120.00
C11—C12—C13	120.0 (3)	C13—C14—H14	120.00
C12—C13—C14	120.1 (3)	C15—C14—H14	120.00
C13—C14—C15	119.9 (3)	C14—C15—H15	120.00
C14—C15—C16	120.7 (3)	C16—C15—H15	120.00
C11—C16—C15	118.9 (3)	C11—C16—H16	121.00
O1—C3—H3A	109.00	C15—C16—H16	121.00
O1—C3—H3B	109.00
C4—O1—C3—C1	−70.7 (3)	N1^i—C2—C10—O2	−83.9 (3)
C3—O1—C4—C5	−13.4 (5)	O1—C4—C5—C6	−178.7 (3)
C3—O1—C4—C9	167.6 (3)	C9—C4—C5—C6	0.3 (6)
C11—O2—C10—C2	−173.0 (2)	O1—C4—C9—C8	179.3 (4)
C10—O2—C11—C12	174.1 (2)	C5—C4—C9—C8	0.2 (6)
C10—O2—C11—C16	−6.9 (4)	C4—C5—C6—C7	−0.4 (6)
C2^i—N1—C1—C2	−0.1 (4)	C5—C6—C7—C8	−0.1 (7)
C2^i—N1—C1—C3	178.5 (3)	C6—C7—C8—C9	0.6 (7)
C1—N1—C2^i—C1^i	0.2 (4)	C7—C8—C9—C4	−0.7 (7)
C1—N1—C2^i—C10^i	−179.6 (3)	O2—C11—C12—C13	179.3 (3)
N1—C1—C2—C10	−179.6 (3)	C16—C11—C12—C13	0.2 (5)
N1—C1—C2—N1^i	0.2 (4)	O2—C11—C16—C15	−179.4 (3)
C3—C1—C2—C10	1.9 (4)	C12—C11—C16—C15	−0.5 (4)
C3—C1—C2—N1^i	−178.3 (3)	C11—C12—C13—C14	−0.3 (5)
N1—C1—C3—O1	130.3 (3)	C12—C13—C14—C15	0.5 (5)
C2—C1—C3—O1	−51.1 (4)	C13—C14—C15—C16	−0.7 (5)
C1—C2—C10—O2	95.9 (3)	C14—C15—C16—C11	0.7 (5)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y−1, z; (iii) x, y+1, z; (iv) x, −y+1/2, z+1/2; (v) −x+1, y−1/2, −z+1/2; (vi) −x+1, y+1/2, −z+1/2; (vii) x, −y+3/2, z+1/2; (viii) −x, y−1/2, −z+1/2; (ix) −x, y+1/2, −z+1/2; (x) x, −y+3/2, z−1/2; (xi) x, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O1	0.98	2.53	2.977 (3)	108
C10—H10A···C^v	0.98	2.89	3.741 (3)	147

Symmetry code: (v) −x+1, y−1/2, −z+1/2.

(II) 2,3,5,6-tetrakis(phenylsulfanylmethyl)pyrazine

Crystal data

C32H28N2S4	Z = 1
Mr = 568.80	F(000) = 298
Triclinic, P1	Dx = 1.352 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4278 (7) Å	Cell parameters from 13043 reflections
b = 9.7152 (12) Å	θ = 1.7–29.6°
c = 12.0602 (12) Å	µ = 0.37 mm^−1
α = 91.152 (10)°	T = 173 K
β = 102.748 (8)°	Rod, colourless
γ = 107.217 (8)°	0.37 × 0.14 × 0.12 mm
V = 698.69 (13) Å^3

Data collection

Stoe IPDS-2 diffractometer	3763 independent reflections
Radiation source: fine-focus sealed tube	3155 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 6.67 pixels mm^-1	θmax = 29.3°, θmin = 1.7°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (PLATON; Spek, 2003)	k = −13→13
Tmin = 0.741, Tmax = 0.956	l = −16→16
13473 measured reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.082	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0383P)^2 + 0.2065P] where P = (Fo^2 + 2Fc^2)/3
3763 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.88139 (6)	0.44006 (4)	0.30952 (3)	0.0283 (1)
S2	0.53761 (7)	0.12453 (4)	0.60721 (3)	0.0334 (1)
N1	0.68076 (18)	0.56601 (12)	0.45490 (9)	0.0249 (3)
C1	0.6127 (2)	0.42252 (14)	0.45821 (10)	0.0241 (3)
C2	0.4298 (2)	0.35575 (13)	0.50358 (10)	0.0241 (3)
C3	0.7426 (2)	0.33863 (15)	0.41165 (12)	0.0297 (4)
C4	0.9808 (2)	0.30951 (14)	0.25133 (11)	0.0263 (3)
C5	1.1901 (2)	0.36045 (15)	0.22669 (11)	0.0293 (4)
C6	1.2750 (2)	0.26807 (17)	0.17372 (13)	0.0355 (4)
C7	1.1530 (3)	0.12416 (18)	0.14602 (15)	0.0429 (5)
C8	0.9450 (3)	0.07290 (18)	0.17016 (17)	0.0490 (6)
C9	0.8574 (3)	0.16465 (16)	0.22226 (15)	0.0401 (5)
C10	0.3432 (2)	0.19504 (14)	0.50951 (11)	0.0291 (4)
C11	0.5752 (2)	0.21852 (14)	0.74085 (11)	0.0281 (4)
C12	0.7789 (3)	0.23755 (17)	0.81845 (13)	0.0376 (4)
C13	0.8173 (3)	0.3008 (2)	0.92805 (14)	0.0440 (5)
C14	0.6543 (3)	0.34795 (18)	0.96017 (13)	0.0398 (5)
C15	0.4543 (3)	0.33220 (16)	0.88279 (13)	0.0351 (4)
C16	0.4119 (2)	0.26722 (15)	0.77295 (12)	0.0305 (4)
H3A	0.63950	0.24400	0.37390	0.0360*
H3B	0.85560	0.32030	0.47500	0.0360*
H5	1.27590	0.45930	0.24620	0.0350*
H6	1.41760	0.30430	0.15660	0.0430*
H7	1.21160	0.06070	0.11060	0.0520*
H8	0.86060	−0.02630	0.15100	0.0590*
H9	0.71350	0.12820	0.23790	0.0480*
H10A	0.31120	0.14570	0.43220	0.0350*
H10B	0.20030	0.17190	0.53390	0.0350*
H12	0.89240	0.20710	0.79620	0.0450*
H13	0.95560	0.31170	0.98120	0.0530*
H14	0.68030	0.39110	1.03540	0.0480*
H15	0.34380	0.36620	0.90480	0.0420*
H16	0.27290	0.25610	0.72030	0.0370*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0336 (2)	0.0250 (2)	0.0308 (2)	0.0122 (1)	0.0127 (1)	0.0019 (1)
S2	0.0540 (2)	0.0264 (2)	0.0291 (2)	0.0225 (2)	0.0147 (2)	0.0031 (1)
N1	0.0286 (5)	0.0253 (5)	0.0235 (5)	0.0120 (4)	0.0067 (4)	0.0002 (4)
C1	0.0287 (6)	0.0249 (6)	0.0218 (5)	0.0129 (5)	0.0059 (5)	−0.0001 (4)
C2	0.0288 (6)	0.0239 (6)	0.0208 (5)	0.0114 (5)	0.0042 (5)	−0.0005 (4)
C3	0.0378 (7)	0.0283 (6)	0.0317 (6)	0.0172 (6)	0.0162 (6)	0.0043 (5)
C4	0.0288 (6)	0.0263 (6)	0.0266 (6)	0.0107 (5)	0.0091 (5)	0.0015 (5)
C5	0.0287 (6)	0.0312 (7)	0.0275 (6)	0.0073 (5)	0.0084 (5)	0.0016 (5)
C6	0.0310 (7)	0.0455 (8)	0.0348 (7)	0.0145 (6)	0.0136 (6)	0.0040 (6)
C7	0.0529 (9)	0.0387 (8)	0.0505 (9)	0.0228 (7)	0.0276 (8)	0.0029 (7)
C8	0.0610 (11)	0.0264 (7)	0.0672 (11)	0.0088 (7)	0.0375 (9)	−0.0021 (7)
C9	0.0399 (8)	0.0287 (7)	0.0550 (9)	0.0048 (6)	0.0268 (7)	−0.0036 (6)
C10	0.0370 (7)	0.0226 (6)	0.0287 (6)	0.0097 (5)	0.0093 (5)	−0.0015 (5)
C11	0.0396 (7)	0.0217 (6)	0.0275 (6)	0.0117 (5)	0.0139 (5)	0.0046 (5)
C12	0.0424 (8)	0.0414 (8)	0.0364 (7)	0.0219 (7)	0.0119 (6)	0.0046 (6)
C13	0.0464 (9)	0.0532 (10)	0.0334 (7)	0.0208 (8)	0.0042 (7)	0.0020 (7)
C14	0.0518 (9)	0.0401 (8)	0.0284 (7)	0.0127 (7)	0.0138 (6)	−0.0002 (6)
C15	0.0435 (8)	0.0328 (7)	0.0350 (7)	0.0128 (6)	0.0201 (6)	0.0016 (6)
C16	0.0340 (7)	0.0280 (6)	0.0315 (6)	0.0090 (5)	0.0125 (5)	0.0021 (5)

Geometric parameters (Å, º)

S1—C3	1.8159 (15)	C13—C14	1.383 (3)
S1—C4	1.7752 (14)	C14—C15	1.377 (3)
S2—C10	1.8189 (14)	C15—C16	1.390 (2)
S2—C11	1.7687 (14)	C3—H3A	0.9900
N1—C1	1.3361 (17)	C3—H3B	0.9900
N1—C2^i	1.3398 (18)	C5—H5	0.9500
C1—C2	1.3961 (19)	C6—H6	0.9500
C1—C3	1.5060 (19)	C7—H7	0.9500
C2—C10	1.5034 (18)	C8—H8	0.9500
C4—C5	1.390 (2)	C9—H9	0.9500
C4—C9	1.389 (2)	C10—H10A	0.9900
C5—C6	1.390 (2)	C10—H10B	0.9900
C6—C7	1.378 (2)	C12—H12	0.9500
C7—C8	1.380 (3)	C13—H13	0.9500
C8—C9	1.392 (3)	C14—H14	0.9500
C11—C12	1.391 (2)	C15—H15	0.9500
C11—C16	1.393 (2)	C16—H16	0.9500
C12—C13	1.385 (2)
S1···N1	2.8426 (13)	C14···H6^viii	3.0600
S1···N1^ii	3.5458 (13)	C15···H5^ii	2.9600
S1···C1^ii	3.6693 (14)	C15···H8^iii	3.0200
S2···C3	3.4017 (15)	C16···H10B	2.9000
S2···S2^iii	3.3585 (7)	C16···H5^ii	2.8700
S1···H6^iv	3.0300	C16···H8^iii	2.7800
S2···H3A	3.1900	H3A···S2	3.1900
S2···H3B	3.1000	H3A···C6^iv	3.0400
S2···H10A^iii	3.1200	H3A···C9	2.7600
N1···S1	2.8426 (13)	H3A···C10	2.7200
N1···S1^ii	3.5458 (13)	H3A···H9	2.1800
N1···N1^i	2.7633 (17)	H3A···H10A	2.3100
N1···C16^i	3.2494 (18)	H3B···S2	3.1000
N1···H3B^ii	2.7800	H3B···N1^ii	2.7800
N1···H16^i	2.7700	H5···C1^v	3.0700
C1···C5^iv	3.3398 (19)	H5···C11^ii	2.9800
C1···S1^ii	3.6693 (14)	H5···C15^ii	2.9600
C2···C16	3.3949 (19)	H5···C16^ii	2.8700
C2···C5^iv	3.3622 (18)	H6···S1^v	3.0300
C3···C6^iv	3.554 (2)	H6···C14^ix	3.0600
C3···S2	3.4017 (15)	H6···H14^ix	2.4500
C5···C2^v	3.3622 (18)	H7···C12^vii	3.0500
C5···C1^v	3.3398 (19)	H8···C15^iii	3.0200
C6···C3^v	3.554 (2)	H8···C16^iii	2.7800
C8···C16^iii	3.599 (2)	H9···C3	2.8300
C16···N1^i	3.2494 (18)	H9···H3A	2.1800
C16···C2	3.3949 (19)	H10A···C3	2.9200
C16···C8^iii	3.599 (2)	H10A···H3A	2.3100
C1···H5^iv	3.0700	H10A···S2^iii	3.1200
C2···H16	3.0800	H10B···C16	2.9000
C3···H10A	2.9200	H10B···H16	2.2800
C3···H9	2.8300	H13···C5^x	2.9700
C5···H13^vi	2.9700	H13···C6^x	2.8700
C6···H13^vi	2.8700	H13···C7^x	3.0500
C6···H3A^v	3.0400	H14···H6^viii	2.4500
C7···H13^vi	3.0500	H14···H15^xi	2.5100
C9···H3A	2.7600	H15···H14^xi	2.5100
C10···H16	2.7600	H16···C2	3.0800
C10···H3A	2.7200	H16···C10	2.7600
C11···H5^ii	2.9800	H16···H10B	2.2800
C12···H7^vii	3.0500	H16···N1^i	2.7700
C3—S1—C4	101.23 (6)	C1—C3—H3A	110.00
C10—S2—C11	104.03 (6)	C1—C3—H3B	110.00
C1—N1—C2^i	118.55 (12)	H3A—C3—H3B	108.00
N1—C1—C2	120.63 (12)	C4—C5—H5	120.00
N1—C1—C3	116.91 (12)	C6—C5—H5	120.00
C2—C1—C3	122.46 (12)	C5—C6—H6	120.00
C1—C2—C10	123.55 (12)	C7—C6—H6	120.00
N1^i—C2—C1	120.82 (11)	C6—C7—H7	120.00
N1^i—C2—C10	115.63 (11)	C8—C7—H7	120.00
S1—C3—C1	109.96 (9)	C7—C8—H8	120.00
S1—C4—C5	116.52 (10)	C9—C8—H8	120.00
S1—C4—C9	124.32 (12)	C4—C9—H9	120.00
C5—C4—C9	118.99 (14)	C8—C9—H9	120.00
C4—C5—C6	120.61 (13)	S2—C10—H10A	109.00
C5—C6—C7	120.21 (15)	S2—C10—H10B	109.00
C6—C7—C8	119.47 (16)	C2—C10—H10A	109.00
C7—C8—C9	120.83 (16)	C2—C10—H10B	109.00
C4—C9—C8	119.87 (17)	H10A—C10—H10B	108.00
S2—C10—C2	113.40 (9)	C11—C12—H12	120.00
S2—C11—C12	116.25 (11)	C13—C12—H12	120.00
S2—C11—C16	124.12 (11)	C12—C13—H13	120.00
C12—C11—C16	119.57 (13)	C14—C13—H13	120.00
C11—C12—C13	120.33 (17)	C13—C14—H14	120.00
C12—C13—C14	120.05 (17)	C15—C14—H14	120.00
C13—C14—C15	119.79 (15)	C14—C15—H15	120.00
C14—C15—C16	120.90 (17)	C16—C15—H15	120.00
C11—C16—C15	119.35 (14)	C11—C16—H16	120.00
S1—C3—H3A	110.00	C15—C16—H16	120.00
S1—C3—H3B	110.00
C4—S1—C3—C1	−170.92 (9)	N1^i—C2—C10—S2	−113.06 (11)
C3—S1—C4—C5	−142.36 (11)	S1—C4—C5—C6	−175.57 (11)
C3—S1—C4—C9	42.31 (14)	C9—C4—C5—C6	0.0 (2)
C11—S2—C10—C2	59.68 (11)	S1—C4—C9—C8	175.77 (13)
C10—S2—C11—C12	−152.28 (11)	C5—C4—C9—C8	0.5 (2)
C10—S2—C11—C16	30.61 (13)	C4—C5—C6—C7	−0.7 (2)
C2^i—N1—C1—C2	0.24 (18)	C5—C6—C7—C8	0.7 (3)
C2^i—N1—C1—C3	−179.48 (11)	C6—C7—C8—C9	−0.1 (3)
C1—N1—C2^i—C1^i	−0.24 (18)	C7—C8—C9—C4	−0.5 (3)
C1—N1—C2^i—C10^i	179.67 (11)	S2—C11—C12—C13	−175.44 (13)
N1—C1—C2—C10	179.66 (12)	C16—C11—C12—C13	1.8 (2)
N1—C1—C2—N1^i	−0.25 (19)	S2—C11—C16—C15	176.07 (11)
C3—C1—C2—C10	−0.63 (19)	C12—C11—C16—C15	−1.0 (2)
C3—C1—C2—N1^i	179.46 (12)	C11—C12—C13—C14	−1.2 (3)
N1—C1—C3—S1	−24.23 (14)	C12—C13—C14—C15	−0.2 (3)
C2—C1—C3—S1	156.05 (10)	C13—C14—C15—C16	1.1 (2)
C1—C2—C10—S2	67.03 (14)	C14—C15—C16—C11	−0.5 (2)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1; (iii) −x+1, −y, −z+1; (iv) x−1, y, z; (v) x+1, y, z; (vi) x, y, z−1; (vii) −x+2, −y, −z+1; (viii) x−1, y, z+1; (ix) x+1, y, z−1; (x) x, y, z+1; (xi) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···C^ii	0.95	2.74	3.528 (2)	141
C13—H13···B^x	0.95	2.81	3.528 (29	133

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