Hydrogen bonding in two salts of 3-methylthio-4-(propargylthio)quinoline

In 3-methyl­thio-4-(propargyl­thio)­quinolinium chloride monohydrate, C₁₃H₁₂NS₂⁺·Cl⁻·H₂O, and 3-methyl­thio-4-(propargyl­thio)­quinolinium tri­chloro­acetate, C₁₃H₁₂­NS₂⁺·­C₂Cl₃O₂⁻, the terminal alkyne group forms C[triple bond]C—H...O hydrogen bonds of favourable geometry. The conformation of the flexible propargyl­thio group is different in the two structures.

Computing details

For both compounds, data collection: please provide details; cell refinement: please provide details; data reduction: please provide details; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

(II) 3-Methylthio-4-propargylthioquinolinium chloride monohydrate

Crystal data

C13H12NS2^+·Cl^−·H2O	Z = 2
Mr = 299.85	F(000) = 312
Triclinic, P1	Dx = 1.428 Mg m^−3
a = 7.571 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.486 (6) Å	Cell parameters from 39 reflections
c = 10.528 (4) Å	θ = 5.1–16.2°
α = 85.72 (4)°	µ = 0.56 mm^−1
β = 71.16 (4)°	T = 293 K
γ = 76.94 (5)°	Needle, yellow
V = 697.1 (6) Å^3	0.65 × 0.10 × 0.05 mm

Data collection

STOE four-circle diffractometer	Rint = 0.035
Radiation source: fine-focus sealed tube	θmax = 27.5°, θmin = 2.0°
Graphite monochromator	h = −6→9
ω scans	k = −12→12
3330 measured reflections	l = −9→13
3149 independent reflections	3 standard reflections every 90 min
2429 reflections with I > 2σ(I)	intensity decay: 4%

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0789P)^2 + 0.2963P] where P = (Fo^2 + 2Fc^2)/3
3149 reflections	(Δ/σ)max = 0.001
179 parameters	Δρmax = 0.46 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl	0.51162 (15)	1.17671 (9)	0.59063 (8)	0.0671 (3)
OW1	0.1414 (6)	0.0961 (4)	1.5305 (3)	0.1142 (12)
S1	0.22133 (11)	0.57394 (7)	0.84116 (7)	0.0489 (2)
S2	0.10128 (11)	0.67154 (9)	1.13383 (7)	0.0505 (2)
N1	0.3469 (3)	0.9640 (2)	0.7999 (2)	0.0388 (5)
H1	0.389 (5)	1.019 (4)	0.730 (4)	0.059 (9)*
C2	0.3278 (4)	0.8362 (3)	0.7718 (3)	0.0404 (5)
H2	0.3650	0.8074	0.6828	0.068 (10)*
C3	0.2524 (3)	0.7437 (3)	0.8740 (3)	0.0365 (5)
C4	0.1989 (3)	0.7888 (3)	1.0061 (2)	0.0355 (5)
C5	0.2159 (3)	0.9282 (3)	1.0348 (2)	0.0357 (5)
C6	0.1564 (4)	0.9872 (3)	1.1653 (3)	0.0442 (6)
H6	0.1020	0.9334	1.2393	0.043 (7)*
C7	0.1781 (4)	1.1217 (3)	1.1832 (3)	0.0518 (7)
H7	0.1402	1.1580	1.2698	0.065 (10)*
C8	0.2563 (4)	1.2073 (3)	1.0742 (3)	0.0501 (7)
H8	0.2699	1.2991	1.0889	0.062 (10)*
C9	0.3123 (4)	1.1559 (3)	0.9471 (3)	0.0431 (6)
H9	0.3630	1.2127	0.8745	0.062 (10)*
C10	0.2930 (3)	1.0161 (3)	0.9261 (2)	0.0356 (5)
C11	0.2826 (5)	0.5702 (4)	0.6626 (3)	0.0581 (8)
H11A	0.1966	0.6466	0.6339	0.060 (10)*
H11B	0.2730	0.4787	0.6352	0.082 (12)*
H11C	0.4111	0.5834	0.6227	0.082 (12)*
C12	0.2750 (7)	0.6326 (5)	1.2213 (5)	0.0879 (15)
H12A	0.4030	0.6110	1.1578	0.19 (3)*
H12B	0.2634	0.7155	1.2744	0.21 (4)*
C13	0.2397 (5)	0.5092 (3)	1.3075 (3)	0.0572 (8)
C14	0.2087 (5)	0.4110 (4)	1.3768 (3)	0.0629 (8)
H14	0.1838	0.3322	1.4325	0.090 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.1072 (7)	0.0542 (4)	0.0441 (4)	−0.0416 (4)	−0.0150 (4)	0.0088 (3)
OW1	0.119 (3)	0.132 (3)	0.072 (2)	−0.020 (2)	−0.0117 (18)	0.0213 (19)
S1	0.0609 (4)	0.0384 (3)	0.0516 (4)	−0.0217 (3)	−0.0159 (3)	0.0002 (3)
S2	0.0549 (4)	0.0644 (5)	0.0449 (4)	−0.0363 (4)	−0.0214 (3)	0.0205 (3)
N1	0.0435 (11)	0.0392 (11)	0.0360 (11)	−0.0177 (9)	−0.0111 (9)	0.0069 (9)
C2	0.0472 (14)	0.0424 (13)	0.0345 (12)	−0.0183 (11)	−0.0111 (10)	0.0020 (10)
C3	0.0365 (12)	0.0356 (11)	0.0410 (13)	−0.0130 (9)	−0.0139 (10)	0.0026 (9)
C4	0.0339 (11)	0.0403 (12)	0.0349 (12)	−0.0144 (10)	−0.0113 (9)	0.0065 (9)
C5	0.0314 (11)	0.0390 (12)	0.0375 (12)	−0.0093 (9)	−0.0112 (9)	0.0010 (9)
C6	0.0440 (14)	0.0487 (14)	0.0373 (13)	−0.0094 (11)	−0.0095 (10)	0.0001 (11)
C7	0.0547 (16)	0.0527 (16)	0.0462 (15)	−0.0047 (13)	−0.0149 (13)	−0.0143 (12)
C8	0.0513 (16)	0.0407 (14)	0.0629 (18)	−0.0109 (12)	−0.0214 (13)	−0.0095 (12)
C9	0.0428 (13)	0.0390 (13)	0.0508 (15)	−0.0154 (11)	−0.0157 (11)	0.0042 (11)
C10	0.0312 (11)	0.0387 (12)	0.0393 (12)	−0.0107 (9)	−0.0124 (9)	0.0018 (9)
C11	0.070 (2)	0.0536 (17)	0.0553 (18)	−0.0206 (15)	−0.0182 (15)	−0.0129 (14)
C12	0.100 (3)	0.079 (3)	0.127 (4)	−0.055 (2)	−0.083 (3)	0.060 (3)
C13	0.0674 (19)	0.0542 (17)	0.0619 (19)	−0.0211 (15)	−0.0337 (16)	0.0134 (14)
C14	0.085 (2)	0.0581 (18)	0.0550 (18)	−0.0252 (17)	−0.0309 (17)	0.0136 (15)

Geometric parameters (Å, º)

S1—C3	1.753 (3)	C7—C8	1.402 (5)
S1—C11	1.786 (3)	C7—H7	0.9300
S2—C4	1.760 (3)	C8—C9	1.358 (4)
S2—C12	1.796 (4)	C8—H8	0.9300
N1—C2	1.319 (3)	C9—C10	1.408 (4)
N1—C10	1.355 (3)	C9—H9	0.9300
N1—H1	0.88 (4)	C11—H11A	0.9600
C2—C3	1.394 (4)	C11—H11B	0.9600
C2—H2	0.9300	C11—H11C	0.9600
C3—C4	1.388 (4)	C12—C13	1.446 (5)
C4—C5	1.421 (3)	C12—H12A	0.9700
C5—C10	1.411 (3)	C12—H12B	0.9700
C5—C6	1.416 (4)	C13—C14	1.159 (4)
C6—C7	1.357 (4)	C14—H14	0.9300
C6—H6	0.9300
C3—S1—C11	103.84 (14)	C9—C8—C7	120.0 (3)
C4—S2—C12	101.79 (16)	C9—C8—H8	120.0
C2—N1—C10	123.7 (2)	C7—C8—H8	120.0
C2—N1—H1	116 (2)	C8—C9—C10	119.5 (3)
C10—N1—H1	120 (2)	C8—C9—H9	120.2
N1—C2—C3	120.8 (2)	C10—C9—H9	120.2
N1—C2—H2	119.6	N1—C10—C9	120.1 (2)
C3—C2—H2	119.6	N1—C10—C5	118.7 (2)
C4—C3—C2	118.5 (2)	C9—C10—C5	121.2 (2)
C4—C3—S1	119.23 (19)	S1—C11—H11A	109.5
C2—C3—S1	122.3 (2)	S1—C11—H11B	109.5
C3—C4—C5	120.1 (2)	H11A—C11—H11B	109.5
C3—C4—S2	117.91 (19)	S1—C11—H11C	109.5
C5—C4—S2	121.89 (19)	H11A—C11—H11C	109.5
C10—C5—C6	117.3 (2)	H11B—C11—H11C	109.5
C10—C5—C4	118.2 (2)	C13—C12—S2	107.7 (2)
C6—C5—C4	124.5 (2)	C13—C12—H12A	110.2
C7—C6—C5	120.5 (3)	S2—C12—H12A	110.2
C7—C6—H6	119.8	C13—C12—H12B	110.2
C5—C6—H6	119.8	S2—C12—H12B	110.2
C6—C7—C8	121.5 (3)	H12A—C12—H12B	108.5
C6—C7—H7	119.2	C14—C13—C12	179.0 (4)
C8—C7—H7	119.2	C13—C14—H14	180.0
C10—N1—C2—C3	−1.4 (4)	C10—C5—C6—C7	−1.6 (4)
N1—C2—C3—C4	−0.3 (4)	C4—C5—C6—C7	−179.9 (3)
N1—C2—C3—S1	179.1 (2)	C5—C6—C7—C8	1.1 (4)
C11—S1—C3—C4	173.8 (2)	C6—C7—C8—C9	0.0 (5)
C11—S1—C3—C2	−5.6 (3)	C7—C8—C9—C10	−0.7 (4)
C2—C3—C4—C5	1.9 (4)	C2—N1—C10—C9	−177.8 (2)
S1—C3—C4—C5	−177.52 (18)	C2—N1—C10—C5	1.5 (4)
C2—C3—C4—S2	179.21 (19)	C8—C9—C10—N1	179.5 (2)
S1—C3—C4—S2	−0.2 (3)	C8—C9—C10—C5	0.2 (4)
C12—S2—C4—C3	116.8 (3)	C6—C5—C10—N1	−178.4 (2)
C12—S2—C4—C5	−65.9 (3)	C4—C5—C10—N1	0.1 (3)
C3—C4—C5—C10	−1.8 (3)	C6—C5—C10—C9	0.9 (4)
S2—C4—C5—C10	−178.97 (18)	C4—C5—C10—C9	179.4 (2)
C3—C4—C5—C6	176.6 (2)	C4—S2—C12—C13	−165.5 (3)
S2—C4—C5—C6	−0.6 (4)

(III) 4-Methylthio-3-propargylthioquinolinium trichloroacetate

Crystal data

C13H12NS2^+·C2Cl3O2^−	F(000) = 1664
Mr = 408.73	Dx = 1.537 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.430 (11) Å	Cell parameters from 26 reflections
b = 5.338 (3) Å	θ = 5.0–15.1°
c = 36.66 (3) Å	µ = 0.76 mm^−1
β = 111.67 (5)°	T = 293 K
V = 3533 (4) Å^3	Needle, yellow
Z = 8	1.2 × 0.1 × 0.05 mm

Data collection

STOE four-circle diffractometer	Rint = 0.032
Radiation source: fine-focus sealed tube	θmax = 27.5°, θmin = 2.1°
Graphite monochromator	h = −24→24
ω scans	k = −6→2
4098 measured reflections	l = −42→47
4031 independent reflections	3 standard reflections every 90 min
2781 reflections with I > 2σ(I)	intensity decay: 6%

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.165	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0764P)^2 + 5.2477P] where P = (Fo^2 + 2Fc^2)/3
4031 reflections	(Δ/σ)max < 0.001
224 parameters	Δρmax = 0.56 e Å^−3
0 restraints	Δρmin = −0.43 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.14430 (6)	0.3416 (2)	0.03462 (3)	0.0626 (3)
S2	0.05253 (5)	−0.00203 (18)	0.07042 (3)	0.0556 (3)
N1	0.19773 (15)	0.6183 (5)	0.14213 (8)	0.0412 (6)
H1	0.230 (2)	0.741 (9)	0.1550 (12)	0.066 (13)*
C2	0.19199 (18)	0.5839 (7)	0.10568 (10)	0.0440 (8)
H2	0.2172	0.6907	0.0949	0.053 (11)*
C3	0.14879 (18)	0.3902 (7)	0.08256 (9)	0.0422 (7)
C4	0.10912 (16)	0.2401 (6)	0.09870 (9)	0.0393 (7)
C5	0.11634 (16)	0.2755 (6)	0.13815 (9)	0.0385 (7)
C6	0.08055 (19)	0.1282 (7)	0.15765 (11)	0.0487 (8)
H6	0.0490	0.0004	0.1441	0.041 (9)*
C7	0.0912 (2)	0.1687 (8)	0.19567 (12)	0.0555 (9)
H7	0.0672	0.0673	0.2079	0.047 (10)*
C8	0.1381 (2)	0.3624 (8)	0.21719 (11)	0.0560 (10)
H8	0.1450	0.3878	0.2434	0.044 (9)*
C9	0.1730 (2)	0.5116 (7)	0.19942 (10)	0.0485 (8)
H9	0.2036	0.6407	0.2134	0.064 (12)*
C10	0.16300 (17)	0.4708 (6)	0.15992 (9)	0.0391 (7)
C11	0.2164 (3)	0.5331 (15)	0.03144 (14)	0.093 (2)
H11A	0.2043	0.7061	0.0330	0.12 (3)*
H11B	0.2222	0.5030	0.0069	0.085 (15)*
H11C	0.2619	0.4940	0.0527	0.089 (17)*
C12	−0.0253 (2)	0.1809 (10)	0.03786 (11)	0.0626 (11)
H12A	−0.0070	0.3007	0.0237	0.103 (19)*
H12B	−0.0593	0.0694	0.0187	0.078 (14)*
C13	−0.0650 (2)	0.3139 (9)	0.05824 (11)	0.0587 (10)
C14	−0.0958 (3)	0.4239 (12)	0.07467 (14)	0.0821 (15)
H14	−0.1206	0.5125	0.0879	0.12 (2)*
Cl1	0.45966 (6)	1.0717 (2)	0.18929 (4)	0.0824 (4)
Cl2	0.38600 (6)	1.48057 (19)	0.14004 (3)	0.0650 (3)
Cl3	0.37079 (7)	1.4117 (2)	0.21391 (3)	0.0720 (3)
O1	0.28681 (14)	0.9747 (5)	0.17708 (7)	0.0529 (6)
O2	0.29272 (14)	1.0461 (5)	0.11853 (7)	0.0526 (6)
C15	0.37879 (18)	1.2549 (6)	0.17346 (11)	0.0450 (8)
C16	0.31214 (17)	1.0752 (6)	0.15390 (10)	0.0401 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0676 (6)	0.0760 (7)	0.0439 (5)	−0.0172 (6)	0.0204 (4)	−0.0110 (5)
S2	0.0545 (5)	0.0417 (5)	0.0617 (6)	−0.0104 (4)	0.0109 (4)	−0.0133 (4)
N1	0.0384 (14)	0.0362 (15)	0.0450 (15)	−0.0057 (12)	0.0107 (12)	−0.0053 (12)
C2	0.0412 (16)	0.0423 (18)	0.0448 (18)	−0.0067 (15)	0.0114 (14)	−0.0011 (15)
C3	0.0392 (16)	0.0425 (18)	0.0389 (16)	−0.0012 (14)	0.0074 (13)	−0.0010 (14)
C4	0.0350 (15)	0.0309 (16)	0.0443 (17)	0.0000 (13)	0.0057 (13)	−0.0027 (13)
C5	0.0329 (15)	0.0319 (16)	0.0451 (17)	0.0009 (12)	0.0076 (13)	0.0021 (13)
C6	0.0449 (18)	0.042 (2)	0.053 (2)	−0.0041 (15)	0.0120 (16)	0.0064 (16)
C7	0.058 (2)	0.051 (2)	0.058 (2)	−0.0021 (19)	0.0221 (18)	0.0125 (18)
C8	0.060 (2)	0.063 (3)	0.0437 (19)	0.009 (2)	0.0181 (17)	0.0079 (18)
C9	0.0476 (18)	0.047 (2)	0.0462 (18)	0.0001 (16)	0.0118 (15)	−0.0052 (16)
C10	0.0372 (15)	0.0324 (16)	0.0430 (17)	0.0016 (13)	0.0093 (13)	0.0004 (13)
C11	0.084 (3)	0.146 (6)	0.056 (3)	−0.049 (4)	0.034 (3)	−0.014 (3)
C12	0.048 (2)	0.084 (3)	0.045 (2)	−0.001 (2)	0.0040 (17)	−0.015 (2)
C13	0.056 (2)	0.068 (3)	0.047 (2)	0.001 (2)	0.0125 (18)	−0.0025 (19)
C14	0.088 (3)	0.099 (4)	0.063 (3)	0.021 (3)	0.032 (3)	0.000 (3)
Cl1	0.0443 (5)	0.0486 (6)	0.1277 (11)	0.0074 (4)	0.0008 (6)	−0.0085 (6)
Cl2	0.0676 (6)	0.0463 (5)	0.0811 (7)	−0.0163 (5)	0.0277 (5)	0.0020 (5)
Cl3	0.0928 (8)	0.0537 (6)	0.0637 (6)	−0.0126 (6)	0.0223 (6)	−0.0244 (5)
O1	0.0593 (15)	0.0478 (15)	0.0528 (14)	−0.0168 (12)	0.0221 (12)	−0.0088 (12)
O2	0.0579 (15)	0.0476 (15)	0.0467 (14)	−0.0133 (12)	0.0128 (12)	−0.0049 (11)
C15	0.0406 (17)	0.0313 (16)	0.056 (2)	−0.0007 (14)	0.0092 (15)	−0.0054 (14)
C16	0.0362 (15)	0.0278 (15)	0.0512 (19)	−0.0001 (13)	0.0102 (14)	−0.0056 (14)

Geometric parameters (Å, º)

S1—C3	1.747 (4)	C8—H8	0.9300
S1—C11	1.773 (5)	C9—C10	1.405 (5)
S2—C4	1.764 (3)	C9—H9	0.9300
S2—C12	1.825 (4)	C11—H11A	0.9600
N1—C2	1.312 (5)	C11—H11B	0.9600
N1—C10	1.351 (4)	C11—H11C	0.9600
N1—H1	0.91 (5)	C12—C13	1.444 (6)
C2—C3	1.402 (5)	C12—H12A	0.9700
C2—H2	0.9300	C12—H12B	0.9700
C3—C4	1.387 (5)	C13—C14	1.154 (6)
C4—C5	1.413 (5)	C14—H14	0.9300
C5—C6	1.407 (5)	Cl1—C15	1.757 (4)
C5—C10	1.419 (4)	Cl2—C15	1.760 (4)
C6—C7	1.349 (5)	Cl3—C15	1.759 (4)
C6—H6	0.9300	O1—C16	1.249 (4)
C7—C8	1.411 (6)	O2—C16	1.219 (4)
C7—H7	0.9300	C15—C16	1.557 (5)
C8—C9	1.359 (5)
C3—S1—C11	103.5 (2)	C10—C9—H9	120.0
C4—S2—C12	100.27 (19)	N1—C10—C9	120.2 (3)
C2—N1—C10	122.7 (3)	N1—C10—C5	119.1 (3)
C2—N1—H1	115 (3)	C9—C10—C5	120.7 (3)
C10—N1—H1	123 (3)	S1—C11—H11A	109.5
N1—C2—C3	121.7 (3)	S1—C11—H11B	109.5
N1—C2—H2	119.1	H11A—C11—H11B	109.5
C3—C2—H2	119.1	S1—C11—H11C	109.5
C4—C3—C2	118.1 (3)	H11A—C11—H11C	109.5
C4—C3—S1	120.9 (3)	H11B—C11—H11C	109.5
C2—C3—S1	120.9 (3)	C13—C12—S2	113.4 (3)
C3—C4—C5	119.9 (3)	C13—C12—H12A	108.9
C3—C4—S2	119.8 (3)	S2—C12—H12A	108.9
C5—C4—S2	120.3 (3)	C13—C12—H12B	108.9
C6—C5—C4	124.4 (3)	S2—C12—H12B	108.9
C6—C5—C10	117.3 (3)	H12A—C12—H12B	107.7
C4—C5—C10	118.4 (3)	C14—C13—C12	178.7 (5)
C7—C6—C5	121.3 (4)	C13—C14—H14	180.0
C7—C6—H6	119.3	C16—C15—Cl1	107.4 (2)
C5—C6—H6	119.3	C16—C15—Cl3	111.3 (2)
C6—C7—C8	121.0 (4)	Cl1—C15—Cl3	109.4 (2)
C6—C7—H7	119.5	C16—C15—Cl2	111.6 (2)
C8—C7—H7	119.5	Cl1—C15—Cl2	108.6 (2)
C9—C8—C7	119.7 (4)	Cl3—C15—Cl2	108.39 (19)
C9—C8—H8	120.1	O2—C16—O1	128.6 (3)
C7—C8—H8	120.1	O2—C16—C15	116.5 (3)
C8—C9—C10	120.0 (3)	O1—C16—C15	114.9 (3)
C8—C9—H9	120.0
C10—N1—C2—C3	0.2 (5)	C6—C7—C8—C9	0.2 (6)
N1—C2—C3—C4	2.7 (5)	C7—C8—C9—C10	−0.7 (6)
N1—C2—C3—S1	−177.9 (3)	C2—N1—C10—C9	178.0 (3)
C11—S1—C3—C4	−169.0 (4)	C2—N1—C10—C5	−2.2 (5)
C11—S1—C3—C2	11.7 (4)	C8—C9—C10—N1	−179.9 (3)
C2—C3—C4—C5	−3.7 (5)	C8—C9—C10—C5	0.3 (5)
S1—C3—C4—C5	177.0 (2)	C6—C5—C10—N1	−179.3 (3)
C2—C3—C4—S2	178.7 (3)	C4—C5—C10—N1	1.1 (5)
S1—C3—C4—S2	−0.6 (4)	C6—C5—C10—C9	0.6 (5)
C12—S2—C4—C3	−75.1 (3)	C4—C5—C10—C9	−179.0 (3)
C12—S2—C4—C5	107.3 (3)	C4—S2—C12—C13	−63.8 (4)
C3—C4—C5—C6	−177.8 (3)	S2—C12—C13—C14	84 (22)
S2—C4—C5—C6	−0.2 (5)	Cl1—C15—C16—O2	−92.3 (3)
C3—C4—C5—C10	1.8 (5)	Cl3—C15—C16—O2	147.8 (3)
S2—C4—C5—C10	179.4 (2)	Cl2—C15—C16—O2	26.6 (4)
C4—C5—C6—C7	178.5 (3)	Cl1—C15—C16—O1	86.0 (3)
C10—C5—C6—C7	−1.1 (5)	Cl3—C15—C16—O1	−33.8 (4)
C5—C6—C7—C8	0.7 (6)	Cl2—C15—C16—O1	−155.1 (3)