Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615003095/yo3004sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615003095/yo300420090914a_0msup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615003095/yo3004091111a_0msup3.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615003095/yo300420090914a_0msup4.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615003095/yo3004091111a_0msup5.cml |
CCDC references: 1049273; 1049272
For both compounds, data collection: SMART (Bruker, 2007); cell refinement: SMART (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008). Molecular graphics: SHELXTL (Sheldrick, 2008) and Marvinsketch (ChemAxon, 2010) for 20090914a_0m; SHELXTL (Sheldrick, 2008) for 091111a_0m. For both compounds, software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
C12H28N+·C2H5N4S2− | F(000) = 736 |
Mr = 335.57 | Dx = 1.171 Mg m−3 Dm = 0 Mg m−3 Dm measured by not measured |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2ybc | Cell parameters from 4223 reflections |
a = 10.1149 (5) Å | θ = 2.7–27.6° |
b = 8.1266 (4) Å | µ = 0.28 mm−1 |
c = 23.1765 (12) Å | T = 296 K |
β = 91.889 (1)° | Block, colorless |
V = 1904.07 (17) Å3 | 0.27 × 0.21 × 0.19 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 4421 independent reflections |
Radiation source: fine-focus sealed tube | 3712 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
phi and ω scans | θmax = 27.7°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −13→12 |
Tmin = 0.928, Tmax = 0.948 | k = −10→10 |
9213 measured reflections | l = −18→30 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0661P)2 + 0.3666P] where P = (Fo2 + 2Fc2)/3 |
4421 reflections | (Δ/σ)max = 0.001 |
205 parameters | Δρmax = 0.28 e Å−3 |
5 restraints | Δρmin = −0.22 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.34365 (4) | 0.08596 (5) | 0.061387 (18) | 0.04437 (13) | |
C1 | 0.42074 (13) | 0.26890 (17) | 0.04504 (6) | 0.0325 (3) | |
N1 | 0.53166 (13) | 0.26269 (16) | 0.01262 (6) | 0.0420 (3) | |
H1A | 0.5561 (19) | 0.1644 (16) | −0.0024 (8) | 0.063* | |
H1B | 0.5635 (19) | 0.3582 (16) | −0.0018 (8) | 0.063* | |
S2 | 0.10000 (4) | 0.55360 (5) | 0.162714 (17) | 0.04495 (13) | |
C2 | 0.23853 (14) | 0.55098 (17) | 0.12321 (6) | 0.0352 (3) | |
N2 | 0.38631 (12) | 0.41678 (14) | 0.06128 (5) | 0.0380 (3) | |
N3 | 0.27427 (12) | 0.41789 (15) | 0.09521 (6) | 0.0386 (3) | |
H3 | 0.2357 (17) | 0.3176 (15) | 0.0988 (8) | 0.058* | |
C3 | 0.80123 (15) | −0.11437 (17) | 0.14528 (7) | 0.0382 (3) | |
H3A | 0.8816 | −0.1731 | 0.1365 | 0.046* | |
H3B | 0.7847 | −0.1326 | 0.1858 | 0.046* | |
N4 | 0.31568 (15) | 0.68418 (18) | 0.11879 (7) | 0.0550 (4) | |
H4C | 0.3890 (15) | 0.678 (3) | 0.0970 (9) | 0.082* | |
H4D | 0.287 (2) | 0.7797 (18) | 0.1342 (9) | 0.082* | |
C4 | 0.68780 (17) | −0.1891 (2) | 0.10968 (8) | 0.0512 (4) | |
H4A | 0.6050 | −0.1384 | 0.1199 | 0.061* | |
H4B | 0.7007 | −0.1699 | 0.0689 | 0.061* | |
C5 | 0.6831 (2) | −0.3709 (2) | 0.12142 (10) | 0.0666 (6) | |
H5A | 0.6122 | −0.4196 | 0.0988 | 0.100* | |
H5B | 0.6687 | −0.3890 | 0.1617 | 0.100* | |
H5C | 0.7655 | −0.4202 | 0.1113 | 0.100* | |
N5 | 0.82528 (11) | 0.06813 (13) | 0.13643 (5) | 0.0311 (2) | |
C6 | 0.70202 (14) | 0.16815 (18) | 0.14756 (6) | 0.0374 (3) | |
H6A | 0.7244 | 0.2839 | 0.1448 | 0.045* | |
H6B | 0.6367 | 0.1444 | 0.1171 | 0.045* | |
C7 | 0.63904 (17) | 0.1394 (3) | 0.20511 (7) | 0.0556 (4) | |
H7A | 0.6052 | 0.0278 | 0.2066 | 0.067* | |
H7B | 0.7050 | 0.1526 | 0.2361 | 0.067* | |
C8 | 0.52761 (19) | 0.2596 (3) | 0.21317 (9) | 0.0653 (5) | |
H8A | 0.4893 | 0.2411 | 0.2500 | 0.098* | |
H8B | 0.4613 | 0.2444 | 0.1830 | 0.098* | |
H8C | 0.5612 | 0.3700 | 0.2116 | 0.098* | |
C9 | 0.93542 (13) | 0.12229 (18) | 0.17863 (6) | 0.0347 (3) | |
H9A | 0.9468 | 0.2403 | 0.1749 | 0.042* | |
H9B | 0.9073 | 0.1009 | 0.2175 | 0.042* | |
C10 | 1.06778 (15) | 0.0412 (2) | 0.17138 (8) | 0.0500 (4) | |
H10A | 1.1028 | 0.0726 | 0.1345 | 0.060* | |
H10B | 1.0571 | −0.0774 | 0.1716 | 0.060* | |
C11 | 1.16393 (18) | 0.0920 (3) | 0.21971 (9) | 0.0631 (5) | |
H11A | 1.2477 | 0.0394 | 0.2145 | 0.095* | |
H11B | 1.1297 | 0.0595 | 0.2561 | 0.095* | |
H11C | 1.1753 | 0.2093 | 0.2191 | 0.095* | |
C12 | 0.86552 (16) | 0.09391 (17) | 0.07440 (6) | 0.0381 (3) | |
H12A | 0.9448 | 0.0298 | 0.0684 | 0.046* | |
H12B | 0.7962 | 0.0495 | 0.0490 | 0.046* | |
C13 | 0.89181 (17) | 0.26855 (19) | 0.05607 (6) | 0.0429 (3) | |
H13A | 0.9518 | 0.3214 | 0.0838 | 0.052* | |
H13B | 0.8098 | 0.3304 | 0.0542 | 0.052* | |
C14 | 0.9530 (2) | 0.2654 (2) | −0.00323 (8) | 0.0639 (5) | |
H14A | 0.9702 | 0.3759 | −0.0155 | 0.096* | |
H14B | 0.8929 | 0.2134 | −0.0305 | 0.096* | |
H14C | 1.0345 | 0.2047 | −0.0010 | 0.096* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0529 (2) | 0.0309 (2) | 0.0504 (2) | −0.00418 (15) | 0.01684 (17) | −0.00244 (15) |
C1 | 0.0330 (6) | 0.0336 (7) | 0.0308 (6) | −0.0015 (5) | 0.0015 (5) | −0.0014 (5) |
N1 | 0.0410 (7) | 0.0367 (7) | 0.0491 (7) | 0.0002 (5) | 0.0146 (5) | −0.0035 (5) |
S2 | 0.0448 (2) | 0.0460 (2) | 0.0449 (2) | −0.00209 (16) | 0.01526 (16) | −0.00844 (16) |
C2 | 0.0379 (7) | 0.0340 (7) | 0.0339 (7) | 0.0005 (6) | 0.0031 (5) | −0.0027 (5) |
N2 | 0.0380 (6) | 0.0327 (6) | 0.0442 (7) | −0.0031 (5) | 0.0131 (5) | −0.0039 (5) |
N3 | 0.0377 (6) | 0.0319 (6) | 0.0470 (7) | −0.0050 (5) | 0.0132 (5) | −0.0056 (5) |
C3 | 0.0423 (8) | 0.0247 (7) | 0.0471 (8) | −0.0011 (6) | −0.0060 (6) | 0.0039 (6) |
N4 | 0.0576 (9) | 0.0383 (7) | 0.0704 (10) | −0.0113 (7) | 0.0246 (7) | −0.0139 (7) |
C4 | 0.0521 (9) | 0.0346 (8) | 0.0657 (10) | −0.0090 (7) | −0.0161 (8) | 0.0023 (7) |
C5 | 0.0623 (11) | 0.0336 (9) | 0.1022 (16) | −0.0082 (8) | −0.0226 (11) | −0.0045 (9) |
N5 | 0.0359 (6) | 0.0258 (5) | 0.0314 (5) | −0.0009 (4) | −0.0016 (4) | −0.0002 (4) |
C6 | 0.0389 (7) | 0.0325 (7) | 0.0408 (7) | 0.0034 (6) | 0.0002 (6) | 0.0026 (6) |
C7 | 0.0501 (9) | 0.0646 (12) | 0.0527 (10) | 0.0091 (8) | 0.0128 (7) | 0.0119 (8) |
C8 | 0.0542 (11) | 0.0719 (13) | 0.0712 (13) | 0.0073 (9) | 0.0212 (9) | −0.0033 (10) |
C9 | 0.0377 (7) | 0.0356 (7) | 0.0307 (6) | −0.0046 (6) | −0.0012 (5) | −0.0022 (5) |
C10 | 0.0353 (8) | 0.0516 (10) | 0.0630 (10) | −0.0045 (7) | 0.0010 (7) | −0.0106 (8) |
C11 | 0.0406 (9) | 0.0837 (15) | 0.0641 (12) | −0.0054 (9) | −0.0091 (8) | 0.0006 (10) |
C12 | 0.0517 (8) | 0.0337 (7) | 0.0287 (6) | 0.0003 (6) | −0.0004 (6) | −0.0027 (5) |
C13 | 0.0545 (9) | 0.0371 (8) | 0.0374 (8) | −0.0047 (7) | 0.0051 (6) | 0.0006 (6) |
C14 | 0.0901 (14) | 0.0614 (12) | 0.0411 (9) | −0.0120 (10) | 0.0140 (9) | 0.0048 (8) |
S1—C1 | 1.7266 (14) | C6—H6A | 0.9700 |
C1—N2 | 1.3099 (17) | C6—H6B | 0.9700 |
C1—N1 | 1.3717 (18) | C7—C8 | 1.508 (2) |
N1—H1A | 0.908 (9) | C7—H7A | 0.9700 |
N1—H1B | 0.908 (9) | C7—H7B | 0.9700 |
S2—C2 | 1.6990 (14) | C8—H8A | 0.9600 |
C2—N3 | 1.3179 (18) | C8—H8B | 0.9600 |
C2—N4 | 1.3403 (19) | C8—H8C | 0.9600 |
N2—N3 | 1.4006 (16) | C9—C10 | 1.507 (2) |
N3—H3 | 0.909 (9) | C9—H9A | 0.9700 |
C3—C4 | 1.518 (2) | C9—H9B | 0.9700 |
C3—N5 | 1.5180 (16) | C10—C11 | 1.516 (2) |
C3—H3A | 0.9700 | C10—H10A | 0.9700 |
C3—H3B | 0.9700 | C10—H10B | 0.9700 |
N4—H4C | 0.912 (9) | C11—H11A | 0.9600 |
N4—H4D | 0.905 (9) | C11—H11B | 0.9600 |
C4—C5 | 1.503 (2) | C11—H11C | 0.9600 |
C4—H4A | 0.9700 | C12—C13 | 1.508 (2) |
C4—H4B | 0.9700 | C12—H12A | 0.9700 |
C5—H5A | 0.9600 | C12—H12B | 0.9700 |
C5—H5B | 0.9600 | C13—C14 | 1.526 (2) |
C5—H5C | 0.9600 | C13—H13A | 0.9700 |
N5—C6 | 1.5175 (18) | C13—H13B | 0.9700 |
N5—C12 | 1.5214 (17) | C14—H14A | 0.9600 |
N5—C9 | 1.5231 (17) | C14—H14B | 0.9600 |
C6—C7 | 1.515 (2) | C14—H14C | 0.9600 |
N2—C1—N1 | 114.91 (12) | C8—C7—H7A | 109.6 |
N2—C1—S1 | 126.91 (10) | C6—C7—H7A | 109.6 |
N1—C1—S1 | 118.16 (10) | C8—C7—H7B | 109.6 |
C1—N1—H1A | 118.7 (13) | C6—C7—H7B | 109.6 |
C1—N1—H1B | 118.4 (13) | H7A—C7—H7B | 108.1 |
H1A—N1—H1B | 120.4 (18) | C7—C8—H8A | 109.5 |
N3—C2—N4 | 117.08 (13) | C7—C8—H8B | 109.5 |
N3—C2—S2 | 121.34 (11) | H8A—C8—H8B | 109.5 |
N4—C2—S2 | 121.58 (11) | C7—C8—H8C | 109.5 |
C1—N2—N3 | 113.26 (11) | H8A—C8—H8C | 109.5 |
C2—N3—N2 | 121.46 (12) | H8B—C8—H8C | 109.5 |
C2—N3—H3 | 124.5 (12) | C10—C9—N5 | 115.83 (12) |
N2—N3—H3 | 113.8 (12) | C10—C9—H9A | 108.3 |
C4—C3—N5 | 116.05 (12) | N5—C9—H9A | 108.3 |
C4—C3—H3A | 108.3 | C10—C9—H9B | 108.3 |
N5—C3—H3A | 108.3 | N5—C9—H9B | 108.3 |
C4—C3—H3B | 108.3 | H9A—C9—H9B | 107.4 |
N5—C3—H3B | 108.3 | C9—C10—C11 | 110.43 (15) |
H3A—C3—H3B | 107.4 | C9—C10—H10A | 109.6 |
C2—N4—H4C | 118.8 (16) | C11—C10—H10A | 109.6 |
C2—N4—H4D | 118.0 (15) | C9—C10—H10B | 109.6 |
H4C—N4—H4D | 123 (2) | C11—C10—H10B | 109.6 |
C5—C4—C3 | 108.81 (14) | H10A—C10—H10B | 108.1 |
C5—C4—H4A | 109.9 | C10—C11—H11A | 109.5 |
C3—C4—H4A | 109.9 | C10—C11—H11B | 109.5 |
C5—C4—H4B | 109.9 | H11A—C11—H11B | 109.5 |
C3—C4—H4B | 109.9 | C10—C11—H11C | 109.5 |
H4A—C4—H4B | 108.3 | H11A—C11—H11C | 109.5 |
C4—C5—H5A | 109.5 | H11B—C11—H11C | 109.5 |
C4—C5—H5B | 109.5 | C13—C12—N5 | 116.82 (11) |
H5A—C5—H5B | 109.5 | C13—C12—H12A | 108.1 |
C4—C5—H5C | 109.5 | N5—C12—H12A | 108.1 |
H5A—C5—H5C | 109.5 | C13—C12—H12B | 108.1 |
H5B—C5—H5C | 109.5 | N5—C12—H12B | 108.1 |
C6—N5—C3 | 111.35 (11) | H12A—C12—H12B | 107.3 |
C6—N5—C12 | 109.50 (10) | C12—C13—C14 | 108.57 (13) |
C3—N5—C12 | 108.14 (10) | C12—C13—H13A | 110.0 |
C6—N5—C9 | 108.88 (10) | C14—C13—H13A | 110.0 |
C3—N5—C9 | 108.22 (10) | C12—C13—H13B | 110.0 |
C12—N5—C9 | 110.75 (11) | C14—C13—H13B | 110.0 |
C7—C6—N5 | 116.02 (12) | H13A—C13—H13B | 108.4 |
C7—C6—H6A | 108.3 | C13—C14—H14A | 109.5 |
N5—C6—H6A | 108.3 | C13—C14—H14B | 109.5 |
C7—C6—H6B | 108.3 | H14A—C14—H14B | 109.5 |
N5—C6—H6B | 108.3 | C13—C14—H14C | 109.5 |
H6A—C6—H6B | 107.4 | H14A—C14—H14C | 109.5 |
C8—C7—C6 | 110.29 (15) | H14B—C14—H14C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···S1i | 0.91 (1) | 2.67 (1) | 3.5641 (13) | 168 (2) |
N1—H1B···N2ii | 0.91 (1) | 2.36 (1) | 3.2404 (18) | 165 (2) |
N3—H3···S1 | 0.91 (1) | 2.36 (2) | 2.9016 (13) | 119 (1) |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, −y+1, −z. |
C16H36N+·C2H5N4S2− | V = 1167.10 (2) Å3 |
Mr = 391.68 | Z = 2 |
Triclinic, P1 | F(000) = 432 |
Hall symbol: -P 1 | Dx = 1.115 Mg m−3 |
a = 9.4151 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.6835 (1) Å | µ = 0.24 mm−1 |
c = 13.4189 (1) Å | T = 296 K |
α = 77.679 (1)° | Block, colorless |
β = 89.246 (1)° | 0.19 × 0.14 × 0.14 mm |
γ = 77.692 (1)° |
Bruker SMART CCD area-detector diffractometer | 5403 independent reflections |
Radiation source: fine-focus sealed tube | 3695 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
phi and ω scans | θmax = 27.7°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −12→12 |
Tmin = 0.956, Tmax = 0.967 | k = −12→6 |
11214 measured reflections | l = −17→17 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.176 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0838P)2 + 0.3749P] where P = (Fo2 + 2Fc2)/3 |
5403 reflections | (Δ/σ)max < 0.001 |
236 parameters | Δρmax = 0.52 e Å−3 |
20 restraints | Δρmin = −0.29 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.1655 (3) | 0.8046 (3) | 0.11557 (18) | 0.0520 (6) | |
N1 | 0.1797 (3) | 0.9408 (3) | 0.1021 (2) | 0.0795 (8) | |
H1A | 0.2517 | 0.9662 | 0.1355 | 0.119* | |
H1B | 0.1297 | 1.0156 | 0.0519 | 0.119* | |
S1 | 0.04522 (8) | 0.75318 (7) | 0.04598 (5) | 0.0614 (2) | |
C2 | 0.3982 (3) | 0.6469 (3) | 0.3276 (2) | 0.0561 (6) | |
N2 | 0.2494 (2) | 0.7077 (2) | 0.18816 (16) | 0.0552 (5) | |
H2A | 0.2534 | 0.6100 | 0.2062 | 0.083* | |
S2 | 0.37415 (8) | 0.47084 (8) | 0.35586 (6) | 0.0691 (2) | |
C3 | 0.8377 (3) | 0.4756 (2) | 0.33086 (16) | 0.0448 (5) | |
H3A | 0.7374 | 0.5278 | 0.3296 | 0.054* | |
H3B | 0.8589 | 0.4115 | 0.3976 | 0.054* | |
N3 | 0.3398 (2) | 0.7510 (2) | 0.25023 (17) | 0.0573 (5) | |
C4 | 0.9349 (3) | 0.5832 (3) | 0.31777 (18) | 0.0508 (5) | |
H4A | 0.9238 | 0.6398 | 0.2483 | 0.061* | |
H4B | 1.0356 | 0.5315 | 0.3293 | 0.061* | |
N4 | 0.4954 (3) | 0.6832 (3) | 0.3868 (2) | 0.0764 (7) | |
H4C | 0.4713 | 0.7803 | 0.3884 | 0.115* | |
H4D | 0.5151 | 0.6277 | 0.4523 | 0.115* | |
C5 | 0.8988 (3) | 0.6838 (3) | 0.39106 (19) | 0.0547 (6) | |
H5A | 0.7983 | 0.7359 | 0.3791 | 0.066* | |
H5B | 0.9090 | 0.6270 | 0.4605 | 0.066* | |
N5 | 0.85265 (19) | 0.38372 (19) | 0.25057 (13) | 0.0408 (4) | |
C6 | 0.9962 (3) | 0.7913 (3) | 0.3792 (2) | 0.0669 (7) | |
H6A | 0.9693 | 0.8534 | 0.4264 | 0.100* | |
H6B | 0.9856 | 0.8484 | 0.3108 | 0.100* | |
H6C | 1.0955 | 0.7402 | 0.3929 | 0.100* | |
C7 | 1.0086 (2) | 0.3057 (2) | 0.24445 (17) | 0.0460 (5) | |
H7A | 1.0667 | 0.3773 | 0.2217 | 0.055* | |
H7B | 1.0129 | 0.2483 | 0.1929 | 0.055* | |
C8 | 1.0769 (3) | 0.2073 (3) | 0.34292 (19) | 0.0557 (6) | |
H8A | 1.0728 | 0.2633 | 0.3952 | 0.067* | |
H8B | 1.0213 | 0.1333 | 0.3654 | 0.067* | |
C9 | 1.2329 (3) | 0.1357 (3) | 0.3307 (2) | 0.0657 (7) | |
H9A | 1.2357 | 0.0716 | 0.2839 | 0.079* | |
H9B | 1.2856 | 0.2094 | 0.3008 | 0.079* | |
C10 | 1.3076 (4) | 0.0508 (4) | 0.4292 (3) | 0.0934 (11) | |
H10A | 1.4063 | 0.0082 | 0.4170 | 0.140* | |
H10B | 1.2576 | −0.0242 | 0.4584 | 0.140* | |
H10C | 1.3070 | 0.1139 | 0.4756 | 0.140* | |
C11 | 0.7537 (2) | 0.2781 (2) | 0.28053 (17) | 0.0459 (5) | |
H11A | 0.7849 | 0.2196 | 0.3478 | 0.055* | |
H11B | 0.6559 | 0.3330 | 0.2856 | 0.055* | |
C12 | 0.7484 (3) | 0.1778 (3) | 0.2089 (2) | 0.0575 (6) | |
H12A | 0.7158 | 0.2346 | 0.1413 | 0.069* | |
H12B | 0.8452 | 0.1206 | 0.2039 | 0.069* | |
C13 | 0.6462 (3) | 0.0780 (3) | 0.2465 (2) | 0.0636 (7) | |
H13A | 0.5501 | 0.1357 | 0.2528 | 0.076* | |
H13B | 0.6798 | 0.0207 | 0.3137 | 0.076* | |
C14 | 0.6360 (4) | −0.0226 (4) | 0.1757 (3) | 0.0863 (10) | |
H14A | 0.5702 | −0.0836 | 0.2026 | 0.129* | |
H14B | 0.7305 | −0.0815 | 0.1704 | 0.129* | |
H14C | 0.6009 | 0.0335 | 0.1094 | 0.129* | |
C15 | 0.8085 (3) | 0.4789 (3) | 0.14491 (16) | 0.0477 (5) | |
H15A | 0.8747 | 0.5441 | 0.1281 | 0.057* | |
H15B | 0.8213 | 0.4172 | 0.0958 | 0.057* | |
C16 | 0.6547 (3) | 0.5682 (3) | 0.13219 (19) | 0.0636 (7) | |
H16A | 0.5877 | 0.5037 | 0.1480 | 0.076* | |
H16B | 0.6410 | 0.6303 | 0.1810 | 0.076* | |
C17 | 0.6181 (6) | 0.6586 (7) | 0.0289 (3) | 0.1396 (19) | 0.50 |
H17A | 0.5132 | 0.6748 | 0.0213 | 0.168* | 0.50 |
H17B | 0.6389 | 0.7516 | 0.0318 | 0.168* | 0.50 |
C17' | 0.6181 (6) | 0.6586 (7) | 0.0289 (3) | 0.1396 (19) | 0.50 |
H17C | 0.5815 | 0.5969 | −0.0080 | 0.168* | 0.50 |
H17D | 0.5343 | 0.7324 | 0.0379 | 0.168* | 0.50 |
C18 | 0.6688 (11) | 0.6318 (16) | −0.0595 (5) | 0.111 (4) | 0.603 (18) |
H18A | 0.6262 | 0.7111 | −0.1140 | 0.167* | 0.603 (18) |
H18B | 0.6441 | 0.5446 | −0.0699 | 0.167* | 0.603 (18) |
H18C | 0.7726 | 0.6204 | −0.0585 | 0.167* | 0.603 (18) |
C18' | 0.6962 (13) | 0.728 (2) | −0.0374 (10) | 0.108 (6) | 0.397 (18) |
H18D | 0.6362 | 0.7810 | −0.0963 | 0.162* | 0.397 (18) |
H18E | 0.7751 | 0.6601 | −0.0575 | 0.162* | 0.397 (18) |
H18F | 0.7344 | 0.7944 | −0.0069 | 0.162* | 0.397 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0593 (15) | 0.0493 (13) | 0.0442 (12) | −0.0090 (11) | 0.0071 (11) | −0.0061 (10) |
N1 | 0.102 (2) | 0.0591 (14) | 0.0760 (16) | −0.0251 (14) | −0.0338 (14) | −0.0011 (12) |
S1 | 0.0777 (5) | 0.0597 (4) | 0.0492 (4) | −0.0228 (3) | −0.0015 (3) | −0.0089 (3) |
C2 | 0.0431 (13) | 0.0590 (15) | 0.0602 (14) | −0.0031 (11) | 0.0018 (11) | −0.0076 (12) |
N2 | 0.0584 (12) | 0.0501 (11) | 0.0579 (12) | −0.0137 (10) | −0.0002 (10) | −0.0112 (10) |
S2 | 0.0654 (5) | 0.0599 (4) | 0.0760 (5) | −0.0102 (3) | −0.0091 (4) | −0.0040 (3) |
C3 | 0.0476 (12) | 0.0504 (12) | 0.0353 (10) | −0.0055 (10) | 0.0032 (9) | −0.0124 (9) |
N3 | 0.0522 (12) | 0.0549 (12) | 0.0645 (13) | −0.0131 (10) | −0.0031 (10) | −0.0107 (10) |
C4 | 0.0556 (14) | 0.0555 (14) | 0.0455 (12) | −0.0147 (11) | 0.0056 (10) | −0.0179 (10) |
N4 | 0.0762 (17) | 0.0691 (15) | 0.0792 (16) | −0.0137 (13) | −0.0220 (13) | −0.0064 (13) |
C5 | 0.0643 (16) | 0.0546 (14) | 0.0494 (13) | −0.0154 (12) | 0.0086 (11) | −0.0181 (11) |
N5 | 0.0437 (10) | 0.0440 (10) | 0.0352 (8) | −0.0105 (8) | 0.0028 (7) | −0.0088 (7) |
C6 | 0.0796 (19) | 0.0664 (17) | 0.0652 (16) | −0.0243 (15) | 0.0112 (14) | −0.0295 (14) |
C7 | 0.0431 (12) | 0.0516 (13) | 0.0452 (11) | −0.0100 (10) | 0.0070 (9) | −0.0151 (10) |
C8 | 0.0474 (13) | 0.0631 (15) | 0.0525 (13) | −0.0030 (11) | 0.0018 (11) | −0.0125 (12) |
C9 | 0.0547 (15) | 0.0749 (18) | 0.0655 (16) | 0.0027 (13) | −0.0019 (13) | −0.0271 (14) |
C10 | 0.071 (2) | 0.101 (3) | 0.085 (2) | 0.0294 (18) | −0.0154 (17) | −0.017 (2) |
C11 | 0.0449 (12) | 0.0470 (12) | 0.0443 (11) | −0.0124 (10) | 0.0031 (9) | −0.0041 (10) |
C12 | 0.0658 (16) | 0.0560 (14) | 0.0567 (14) | −0.0247 (12) | 0.0094 (12) | −0.0141 (12) |
C13 | 0.0670 (17) | 0.0617 (16) | 0.0653 (16) | −0.0273 (13) | 0.0049 (13) | −0.0076 (13) |
C14 | 0.109 (3) | 0.072 (2) | 0.092 (2) | −0.0485 (19) | 0.0015 (19) | −0.0193 (18) |
C15 | 0.0593 (14) | 0.0509 (13) | 0.0343 (10) | −0.0187 (11) | 0.0013 (10) | −0.0051 (9) |
C16 | 0.0684 (17) | 0.0625 (16) | 0.0498 (14) | −0.0029 (13) | −0.0064 (12) | −0.0005 (12) |
C17 | 0.118 (3) | 0.172 (4) | 0.078 (2) | 0.020 (3) | −0.001 (2) | 0.035 (3) |
C17' | 0.118 (3) | 0.172 (4) | 0.078 (2) | 0.020 (3) | −0.001 (2) | 0.035 (3) |
C18 | 0.109 (6) | 0.142 (9) | 0.062 (4) | 0.002 (6) | −0.008 (4) | −0.003 (4) |
C18' | 0.120 (9) | 0.132 (12) | 0.064 (6) | −0.049 (8) | −0.018 (5) | 0.021 (7) |
C1—N1 | 1.327 (3) | C9—C10 | 1.494 (4) |
C1—N2 | 1.330 (3) | C9—H9A | 0.9700 |
C1—S1 | 1.694 (3) | C9—H9B | 0.9700 |
N1—H1A | 0.9197 | C10—H10A | 0.9600 |
N1—H1B | 0.9243 | C10—H10B | 0.9600 |
C2—N3 | 1.315 (3) | C10—H10C | 0.9600 |
C2—N4 | 1.367 (3) | C11—C12 | 1.514 (3) |
C2—S2 | 1.728 (3) | C11—H11A | 0.9700 |
N2—N3 | 1.382 (3) | C11—H11B | 0.9700 |
N2—H2A | 0.9183 | C12—C13 | 1.513 (3) |
C3—C4 | 1.510 (3) | C12—H12A | 0.9700 |
C3—N5 | 1.524 (3) | C12—H12B | 0.9700 |
C3—H3A | 0.9700 | C13—C14 | 1.515 (4) |
C3—H3B | 0.9700 | C13—H13A | 0.9700 |
C4—C5 | 1.514 (3) | C13—H13B | 0.9700 |
C4—H4A | 0.9700 | C14—H14A | 0.9600 |
C4—H4B | 0.9700 | C14—H14B | 0.9600 |
N4—H4C | 0.9241 | C14—H14C | 0.9600 |
N4—H4D | 0.9248 | C15—C16 | 1.512 (4) |
C5—C6 | 1.510 (3) | C15—H15A | 0.9700 |
C5—H5A | 0.9700 | C15—H15B | 0.9700 |
C5—H5B | 0.9700 | C16—C17 | 1.474 (4) |
N5—C7 | 1.512 (3) | C16—H16A | 0.9700 |
N5—C11 | 1.515 (3) | C16—H16B | 0.9700 |
N5—C15 | 1.525 (3) | C17—C18 | 1.329 (8) |
C6—H6A | 0.9600 | C17—H17A | 0.9700 |
C6—H6B | 0.9600 | C17—H17B | 0.9700 |
C6—H6C | 0.9600 | C18—H18A | 0.9600 |
C7—C8 | 1.514 (3) | C18—H18B | 0.9600 |
C7—H7A | 0.9700 | C18—H18C | 0.9600 |
C7—H7B | 0.9700 | C18'—H18D | 0.9600 |
C8—C9 | 1.508 (3) | C18'—H18E | 0.9600 |
C8—H8A | 0.9700 | C18'—H18F | 0.9600 |
C8—H8B | 0.9700 | ||
N1—C1—N2 | 117.0 (2) | C10—C9—H9B | 109.0 |
N1—C1—S1 | 122.7 (2) | C8—C9—H9B | 109.0 |
N2—C1—S1 | 120.27 (19) | H9A—C9—H9B | 107.8 |
C1—N1—H1A | 122.0 | C9—C10—H10A | 109.5 |
C1—N1—H1B | 123.9 | C9—C10—H10B | 109.5 |
H1A—N1—H1B | 113.4 | H10A—C10—H10B | 109.5 |
N3—C2—N4 | 114.4 (2) | C9—C10—H10C | 109.5 |
N3—C2—S2 | 127.3 (2) | H10A—C10—H10C | 109.5 |
N4—C2—S2 | 118.1 (2) | H10B—C10—H10C | 109.5 |
C1—N2—N3 | 120.4 (2) | C12—C11—N5 | 115.72 (18) |
C1—N2—H2A | 127.5 | C12—C11—H11A | 108.3 |
N3—N2—H2A | 112.0 | N5—C11—H11A | 108.3 |
C4—C3—N5 | 114.96 (17) | C12—C11—H11B | 108.3 |
C4—C3—H3A | 108.5 | N5—C11—H11B | 108.3 |
N5—C3—H3A | 108.5 | H11A—C11—H11B | 107.4 |
C4—C3—H3B | 108.5 | C13—C12—C11 | 110.9 (2) |
N5—C3—H3B | 108.5 | C13—C12—H12A | 109.5 |
H3A—C3—H3B | 107.5 | C11—C12—H12A | 109.5 |
C2—N3—N2 | 112.9 (2) | C13—C12—H12B | 109.5 |
C3—C4—C5 | 111.59 (19) | C11—C12—H12B | 109.5 |
C3—C4—H4A | 109.3 | H12A—C12—H12B | 108.0 |
C5—C4—H4A | 109.3 | C12—C13—C14 | 112.5 (2) |
C3—C4—H4B | 109.3 | C12—C13—H13A | 109.1 |
C5—C4—H4B | 109.3 | C14—C13—H13A | 109.1 |
H4A—C4—H4B | 108.0 | C12—C13—H13B | 109.1 |
C2—N4—H4C | 111.7 | C14—C13—H13B | 109.1 |
C2—N4—H4D | 117.1 | H13A—C13—H13B | 107.8 |
H4C—N4—H4D | 110.2 | C13—C14—H14A | 109.5 |
C6—C5—C4 | 112.0 (2) | C13—C14—H14B | 109.5 |
C6—C5—H5A | 109.2 | H14A—C14—H14B | 109.5 |
C4—C5—H5A | 109.2 | C13—C14—H14C | 109.5 |
C6—C5—H5B | 109.2 | H14A—C14—H14C | 109.5 |
C4—C5—H5B | 109.2 | H14B—C14—H14C | 109.5 |
H5A—C5—H5B | 107.9 | C16—C15—N5 | 116.05 (19) |
C7—N5—C11 | 111.42 (17) | C16—C15—H15A | 108.3 |
C7—N5—C3 | 111.24 (16) | N5—C15—H15A | 108.3 |
C11—N5—C3 | 106.71 (16) | C16—C15—H15B | 108.3 |
C7—N5—C15 | 106.36 (16) | N5—C15—H15B | 108.3 |
C11—N5—C15 | 110.61 (16) | H15A—C15—H15B | 107.4 |
C3—N5—C15 | 110.57 (16) | C17—C16—C15 | 113.8 (3) |
C5—C6—H6A | 109.5 | C17—C16—H16A | 108.8 |
C5—C6—H6B | 109.5 | C15—C16—H16A | 108.8 |
H6A—C6—H6B | 109.5 | C17—C16—H16B | 108.8 |
C5—C6—H6C | 109.5 | C15—C16—H16B | 108.8 |
H6A—C6—H6C | 109.5 | H16A—C16—H16B | 107.7 |
H6B—C6—H6C | 109.5 | C18—C17—C16 | 128.3 (6) |
N5—C7—C8 | 115.42 (18) | C18—C17—H17A | 105.2 |
N5—C7—H7A | 108.4 | C16—C17—H17A | 105.2 |
C8—C7—H7A | 108.4 | C18—C17—H17B | 105.2 |
N5—C7—H7B | 108.4 | C16—C17—H17B | 105.2 |
C8—C7—H7B | 108.4 | H17A—C17—H17B | 105.9 |
H7A—C7—H7B | 107.5 | C17—C18—H18A | 109.5 |
C9—C8—C7 | 112.1 (2) | C17—C18—H18B | 109.5 |
C9—C8—H8A | 109.2 | H18A—C18—H18B | 109.5 |
C7—C8—H8A | 109.2 | C17—C18—H18C | 109.5 |
C9—C8—H8B | 109.2 | H18A—C18—H18C | 109.5 |
C7—C8—H8B | 109.2 | H18B—C18—H18C | 109.5 |
H8A—C8—H8B | 107.9 | H18D—C18'—H18E | 109.5 |
C10—C9—C8 | 113.1 (2) | H18D—C18'—H18F | 109.5 |
C10—C9—H9A | 109.0 | H18E—C18'—H18F | 109.5 |
C8—C9—H9A | 109.0 | ||
N1—C1—N2—N3 | 4.0 (4) | N5—C7—C8—C9 | −179.0 (2) |
S1—C1—N2—N3 | −175.09 (17) | C7—C8—C9—C10 | 173.7 (3) |
N4—C2—N3—N2 | 176.0 (2) | C7—N5—C11—C12 | −60.0 (2) |
S2—C2—N3—N2 | 0.5 (3) | C3—N5—C11—C12 | 178.4 (2) |
C1—N2—N3—C2 | 170.1 (2) | C15—N5—C11—C12 | 58.1 (3) |
N5—C3—C4—C5 | 172.01 (19) | N5—C11—C12—C13 | −179.9 (2) |
C3—C4—C5—C6 | 179.5 (2) | C11—C12—C13—C14 | 179.1 (2) |
C4—C3—N5—C7 | 55.1 (2) | C7—N5—C15—C16 | 179.8 (2) |
C4—C3—N5—C11 | 176.80 (19) | C11—N5—C15—C16 | 58.7 (3) |
C4—C3—N5—C15 | −62.8 (2) | C3—N5—C15—C16 | −59.3 (2) |
C11—N5—C7—C8 | −61.1 (2) | N5—C15—C16—C17 | 179.6 (3) |
C3—N5—C7—C8 | 57.9 (2) | C15—C16—C17—C18 | 31.3 (12) |
C15—N5—C7—C8 | 178.31 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···S1i | 0.92 | 2.58 | 3.484 (3) | 164 |
N4—H4D···S2ii | 0.92 | 2.69 | 3.576 (3) | 161 |
N2—H2A···S2 | 0.92 | 2.32 | 2.902 (2) | 121 |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1, −y+1, −z+1. |