Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804020380/bt6497sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804020380/bt6497Isup2.hkl |
CCDC reference: 201294
Key indicators
- Single-crystal X-ray study
- T = 193 K
- Mean (C-C) = 0.006 Å
- Disorder in solvent or counterion
- R factor = 0.052
- wR factor = 0.075
- Data-to-parameter ratio = 17.4
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 32 Perc. PLAT731_ALERT_1_B Bond Calc 0.91(5), Rep 0.899(10) ...... 5.00 su-Rat O2 -H21 1.555 1.555
Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.745 RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.106 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms .. ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for S2 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 40.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT353_ALERT_3_C Long N-H Bond (0.87A) N4 - H4 ... 1.01 Ang. PLAT731_ALERT_1_C Bond Calc 0.89(3), Rep 0.895(10) ...... 3.00 su-Rat O2 -H22 1.555 1.555 PLAT732_ALERT_1_C Angle Calc 109(5), Rep 109.4(16) ...... 3.12 su-Rat H22 -O2 -H21 1.555 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 4 H2 O
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 16 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA WinExpose (Stoe & Cie, 2002); cell refinement: X-AREA WinCell (Stoe & Cie, 2002); data reduction: X-AREA WinIntegrate (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: DIAMOND2 (Crystal Impact, 2000).
2C17H38N+·C16H10N2O7S22−·1.8H2O | Z = 2 |
Mr = 951.78 | F(000) = 1040 |
Triclinic, P1 | Dx = 1.172 Mg m−3 |
a = 8.2811 (14) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.071 (2) Å | Cell parameters from 7804 reflections |
c = 25.204 (4) Å | θ = 1.6–26.0° |
α = 85.82 (1)° | µ = 0.15 mm−1 |
β = 87.96 (1)° | T = 193 K |
γ = 82.54 (1)° | Needle, orange |
V = 2696.9 (7) Å3 | 0.50 × 0.04 × 0.02 mm |
Stoe IPDS-II diffractometer | 10547 independent reflections |
Radiation source: fine-focus sealed tube | 3416 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.106 |
Detector resolution: 150 pixels mm-1 | θmax = 26.2°, θmin = 1.6° |
ω scans | h = −9→10 |
Absorption correction: multi-scan (XPREP in SHELXTL; Siemens, 1996) | k = −16→15 |
Tmin = 0.889, Tmax = 0.997 | l = −31→31 |
23823 measured reflections |
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)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.075 | w = 1/[σ2(Fo2)] |
S = 0.75 | (Δ/σ)max < 0.001 |
10547 reflections | Δρmax = 0.23 e Å−3 |
605 parameters | Δρmin = −0.35 e Å−3 |
7 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00054 (2) |
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) | |
S1 | 0.79371 (13) | 0.01103 (7) | 0.37384 (4) | 0.0352 (3) | |
S2 | 0.64743 (14) | 0.41895 (8) | 0.40115 (4) | 0.0419 (3) | |
N1 | 0.1583 (4) | −0.3599 (2) | 0.39579 (13) | 0.0403 (9) | |
N2 | 0.2511 (4) | 0.0949 (2) | 0.43491 (12) | 0.0361 (8) | |
N3 | 0.8634 (4) | −0.0048 (2) | 0.25755 (12) | 0.0345 (8) | |
N4 | 0.9225 (4) | −0.0704 (2) | 0.22325 (13) | 0.0399 (8) | |
H4 | 0.973 (4) | −0.052 (3) | 0.1875 (7) | 0.048* | |
O1 | 0.5603 (5) | −0.2106 (3) | 0.4131 (2) | 0.080 (2) | 0.803 (8) |
H11 | 0.607 (8) | −0.152 (3) | 0.409 (3) | 0.19 (3)* | 0.803 (8) |
H12 | 0.641 (6) | −0.264 (4) | 0.416 (4) | 0.19 (3)* | 0.803 (8) |
O2 | 0.2847 (4) | 0.3749 (2) | 0.51462 (12) | 0.0573 (8) | |
H22 | 0.275 (8) | 0.435 (2) | 0.530 (2) | 0.19 (2)* | |
H21 | 0.370 (5) | 0.372 (4) | 0.491 (2) | 0.19 (2)* | |
O3 | 1.0299 (4) | 0.0663 (2) | 0.16385 (11) | 0.0545 (8) | |
O11 | 0.9524 (3) | −0.04288 (17) | 0.35998 (9) | 0.0371 (6) | |
O12 | 0.6540 (3) | −0.03404 (19) | 0.35607 (10) | 0.0408 (7) | |
O13 | 0.7782 (3) | 0.02884 (17) | 0.43101 (9) | 0.0429 (7) | |
O21 | 0.5925 (4) | 0.5095 (2) | 0.36670 (11) | 0.0694 (10) | |
O22 | 0.7824 (3) | 0.4334 (2) | 0.43364 (11) | 0.0565 (8) | |
O23 | 0.5177 (3) | 0.3756 (2) | 0.43269 (12) | 0.0697 (10) | |
C1 | 0.7866 (4) | 0.1390 (3) | 0.34114 (14) | 0.0280 (9) | |
C2 | 0.7284 (4) | 0.2172 (3) | 0.37394 (15) | 0.0337 (10) | |
H2A | 0.6897 | 0.1984 | 0.4088 | 0.040* | |
C3 | 0.7240 (4) | 0.3226 (3) | 0.35809 (15) | 0.0345 (9) | |
C4 | 0.7841 (5) | 0.3491 (3) | 0.30792 (15) | 0.0410 (11) | |
H4B | 0.7844 | 0.4200 | 0.2965 | 0.049* | |
C5 | 0.8447 (5) | 0.2729 (3) | 0.27358 (15) | 0.0367 (10) | |
C6 | 0.8399 (5) | 0.1651 (3) | 0.28763 (15) | 0.0332 (10) | |
C7 | 0.9084 (5) | 0.3049 (3) | 0.22187 (15) | 0.0469 (12) | |
H7A | 0.9042 | 0.3768 | 0.2121 | 0.056* | |
C8 | 0.9734 (5) | 0.2373 (3) | 0.18708 (17) | 0.0490 (12) | |
H8A | 1.0222 | 0.2615 | 0.1547 | 0.059* | |
C9 | 0.9696 (5) | 0.1291 (3) | 0.19837 (15) | 0.0422 (11) | |
C10 | 0.8970 (5) | 0.0936 (3) | 0.24786 (14) | 0.0324 (9) | |
C11 | 0.8895 (5) | −0.1746 (3) | 0.22977 (15) | 0.0364 (10) | |
C11N | 0.2760 (5) | −0.3451 (3) | 0.43644 (15) | 0.0534 (12) | |
H11B | 0.2301 | −0.3615 | 0.4720 | 0.080* | |
H11C | 0.2982 | −0.2730 | 0.4335 | 0.080* | |
H11D | 0.3776 | −0.3910 | 0.4308 | 0.080* | |
C12 | 0.9559 (5) | −0.2383 (3) | 0.19115 (17) | 0.0490 (12) | |
H12B | 1.0173 | −0.2119 | 0.1619 | 0.059* | |
C12N | 0.0008 (5) | −0.2957 (3) | 0.40639 (16) | 0.0546 (12) | |
H12C | −0.0390 | −0.3137 | 0.4425 | 0.082* | |
H12D | −0.0790 | −0.3085 | 0.3806 | 0.082* | |
H12E | 0.0163 | −0.2224 | 0.4030 | 0.082* | |
C13 | 0.9313 (6) | −0.3413 (3) | 0.19595 (18) | 0.0586 (13) | |
H13B | 0.9758 | −0.3867 | 0.1699 | 0.070* | |
C13N | 0.1326 (6) | −0.4728 (3) | 0.39953 (17) | 0.0610 (14) | |
H13C | 0.0889 | −0.4917 | 0.4350 | 0.092* | |
H13D | 0.2369 | −0.5156 | 0.3933 | 0.092* | |
H13E | 0.0555 | −0.4843 | 0.3726 | 0.092* | |
C14 | 0.8416 (6) | −0.3779 (3) | 0.23891 (18) | 0.0589 (13) | |
H14A | 0.8248 | −0.4487 | 0.2417 | 0.071* | |
C15 | 0.7761 (5) | −0.3151 (3) | 0.27768 (17) | 0.0511 (12) | |
H15A | 0.7153 | −0.3419 | 0.3070 | 0.061* | |
C16 | 0.8006 (5) | −0.2105 (3) | 0.27323 (15) | 0.0422 (11) | |
H16A | 0.7571 | −0.1652 | 0.2995 | 0.051* | |
C21N | 0.3944 (5) | 0.1208 (3) | 0.46358 (15) | 0.0486 (11) | |
H21B | 0.4952 | 0.0868 | 0.4477 | 0.073* | |
H21C | 0.3860 | 0.0967 | 0.5012 | 0.073* | |
H21D | 0.3957 | 0.1959 | 0.4606 | 0.073* | |
C22N | 0.0972 (5) | 0.1482 (3) | 0.45893 (15) | 0.0506 (12) | |
H22B | 0.0924 | 0.1289 | 0.4972 | 0.076* | |
H22C | 0.0030 | 0.1273 | 0.4421 | 0.076* | |
H22D | 0.0958 | 0.2233 | 0.4532 | 0.076* | |
C23N | 0.2480 (5) | −0.0204 (3) | 0.44129 (15) | 0.0487 (11) | |
H23B | 0.3478 | −0.0557 | 0.4254 | 0.073* | |
H23C | 0.1532 | −0.0381 | 0.4234 | 0.073* | |
H23D | 0.2412 | −0.0425 | 0.4792 | 0.073* | |
C101 | 0.2258 (5) | −0.3346 (3) | 0.33972 (15) | 0.0432 (11) | |
H10A | 0.3299 | −0.3796 | 0.3343 | 0.052* | |
H10B | 0.1484 | −0.3510 | 0.3135 | 0.052* | |
C102 | 0.2552 (5) | −0.2217 (3) | 0.32877 (15) | 0.0428 (11) | |
H10C | 0.1510 | −0.1760 | 0.3326 | 0.051* | |
H10D | 0.3310 | −0.2040 | 0.3552 | 0.051* | |
C103 | 0.3270 (5) | −0.2037 (3) | 0.27281 (14) | 0.0395 (11) | |
H10E | 0.4320 | −0.2488 | 0.2691 | 0.047* | |
H10F | 0.2519 | −0.2223 | 0.2464 | 0.047* | |
C104 | 0.3542 (5) | −0.0912 (3) | 0.26174 (15) | 0.0406 (11) | |
H10G | 0.4272 | −0.0726 | 0.2888 | 0.049* | |
H10H | 0.2487 | −0.0466 | 0.2651 | 0.049* | |
C105 | 0.4295 (5) | −0.0699 (3) | 0.20603 (15) | 0.0440 (11) | |
H10I | 0.3559 | −0.0875 | 0.1789 | 0.053* | |
H10J | 0.5344 | −0.1151 | 0.2025 | 0.053* | |
C106 | 0.4590 (5) | 0.0441 (3) | 0.19529 (16) | 0.0476 (12) | |
H10K | 0.3528 | 0.0886 | 0.1947 | 0.057* | |
H10L | 0.5219 | 0.0640 | 0.2247 | 0.057* | |
C107 | 0.5520 (5) | 0.0631 (3) | 0.14232 (16) | 0.0485 (12) | |
H10M | 0.6642 | 0.0267 | 0.1451 | 0.058* | |
H10N | 0.4982 | 0.0330 | 0.1138 | 0.058* | |
C108 | 0.5602 (5) | 0.1771 (3) | 0.12687 (15) | 0.0461 (11) | |
H10O | 0.6090 | 0.2081 | 0.1562 | 0.055* | |
H10P | 0.4483 | 0.2129 | 0.1222 | 0.055* | |
C109 | 0.6614 (5) | 0.1945 (3) | 0.07512 (16) | 0.0483 (12) | |
H10Q | 0.7745 | 0.1611 | 0.0804 | 0.058* | |
H10R | 0.6154 | 0.1607 | 0.0462 | 0.058* | |
C110 | 0.6642 (5) | 0.3094 (3) | 0.05807 (16) | 0.0495 (12) | |
H11E | 0.5511 | 0.3434 | 0.0535 | 0.059* | |
H11F | 0.7129 | 0.3431 | 0.0865 | 0.059* | |
C111 | 0.7619 (5) | 0.3245 (3) | 0.00600 (16) | 0.0484 (12) | |
H11G | 0.8752 | 0.2912 | 0.0111 | 0.058* | |
H11H | 0.7146 | 0.2889 | −0.0219 | 0.058* | |
C112 | 0.7654 (5) | 0.4377 (3) | −0.01336 (16) | 0.0470 (12) | |
H11I | 0.6528 | 0.4708 | −0.0200 | 0.056* | |
H11J | 0.8098 | 0.4743 | 0.0148 | 0.056* | |
C113 | 0.8692 (5) | 0.4487 (3) | −0.06427 (17) | 0.0556 (13) | |
H11K | 0.8241 | 0.4124 | −0.0923 | 0.067* | |
H11L | 0.9812 | 0.4147 | −0.0576 | 0.067* | |
C114 | 0.8765 (6) | 0.5626 (3) | −0.08460 (18) | 0.0622 (14) | |
H11M | 0.9448 | 0.5649 | −0.1171 | 0.093* | |
H11N | 0.9232 | 0.5989 | −0.0573 | 0.093* | |
H11O | 0.7663 | 0.5964 | −0.0923 | 0.093* | |
C201 | 0.2631 (5) | 0.1237 (3) | 0.37516 (14) | 0.0435 (11) | |
H20A | 0.3679 | 0.0894 | 0.3611 | 0.052* | |
H20B | 0.1746 | 0.0959 | 0.3576 | 0.052* | |
C202 | 0.2524 (5) | 0.2384 (3) | 0.35979 (16) | 0.0457 (11) | |
H20C | 0.3217 | 0.2711 | 0.3831 | 0.055* | |
H20D | 0.1385 | 0.2713 | 0.3642 | 0.055* | |
C203 | 0.3100 (5) | 0.2538 (3) | 0.30148 (15) | 0.0469 (12) | |
H20E | 0.2381 | 0.2230 | 0.2783 | 0.056* | |
H20F | 0.4220 | 0.2180 | 0.2970 | 0.056* | |
C204 | 0.3077 (5) | 0.3697 (3) | 0.28458 (15) | 0.0474 (12) | |
H20G | 0.1935 | 0.4034 | 0.2843 | 0.057* | |
H20H | 0.3663 | 0.4025 | 0.3110 | 0.057* | |
C205 | 0.3870 (5) | 0.3870 (3) | 0.22937 (16) | 0.0493 (12) | |
H20I | 0.3222 | 0.3601 | 0.2025 | 0.059* | |
H20J | 0.4976 | 0.3477 | 0.2287 | 0.059* | |
C206 | 0.3994 (5) | 0.5028 (3) | 0.21447 (16) | 0.0491 (12) | |
H20K | 0.2883 | 0.5405 | 0.2109 | 0.059* | |
H20L | 0.4522 | 0.5317 | 0.2436 | 0.059* | |
C207 | 0.4972 (5) | 0.5204 (3) | 0.16223 (15) | 0.0487 (12) | |
H20M | 0.6098 | 0.4854 | 0.1664 | 0.058* | |
H20N | 0.4475 | 0.4884 | 0.1335 | 0.058* | |
C208 | 0.5031 (5) | 0.6345 (3) | 0.14599 (16) | 0.0515 (12) | |
H20O | 0.5475 | 0.6675 | 0.1755 | 0.062* | |
H20P | 0.3909 | 0.6689 | 0.1399 | 0.062* | |
C209 | 0.6076 (5) | 0.6508 (3) | 0.09574 (16) | 0.0496 (12) | |
H20Q | 0.5607 | 0.6201 | 0.0659 | 0.059* | |
H20R | 0.7186 | 0.6141 | 0.1014 | 0.059* | |
C210 | 0.6192 (5) | 0.7659 (3) | 0.08038 (16) | 0.0529 (12) | |
H21E | 0.5077 | 0.8028 | 0.0762 | 0.063* | |
H21F | 0.6695 | 0.7956 | 0.1098 | 0.063* | |
C211 | 0.7183 (5) | 0.7845 (3) | 0.02898 (17) | 0.0544 (13) | |
H21G | 0.8307 | 0.7493 | 0.0334 | 0.065* | |
H21H | 0.6698 | 0.7532 | −0.0003 | 0.065* | |
C212 | 0.7247 (5) | 0.8990 (3) | 0.01348 (16) | 0.0513 (12) | |
H21I | 0.7763 | 0.9298 | 0.0423 | 0.062* | |
H21J | 0.6121 | 0.9346 | 0.0101 | 0.062* | |
C213 | 0.8194 (6) | 0.9179 (3) | −0.03879 (17) | 0.0550 (13) | |
H21K | 0.7684 | 0.8872 | −0.0677 | 0.066* | |
H21L | 0.9325 | 0.8832 | −0.0355 | 0.066* | |
C214 | 0.8224 (6) | 1.0338 (3) | −0.05334 (17) | 0.0597 (13) | |
H21M | 0.8843 | 1.0430 | −0.0868 | 0.090* | |
H21N | 0.8742 | 1.0643 | −0.0250 | 0.090* | |
H21O | 0.7106 | 1.0681 | −0.0574 | 0.090* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0418 (7) | 0.0271 (5) | 0.0354 (6) | −0.0022 (5) | 0.0003 (5) | 0.0020 (4) |
S2 | 0.0449 (7) | 0.0308 (6) | 0.0490 (7) | 0.0002 (5) | 0.0078 (6) | −0.0087 (5) |
N1 | 0.041 (2) | 0.035 (2) | 0.042 (2) | 0.0003 (17) | 0.0092 (18) | 0.0042 (16) |
N2 | 0.035 (2) | 0.0382 (19) | 0.0352 (19) | −0.0051 (16) | 0.0009 (15) | −0.0013 (15) |
N3 | 0.033 (2) | 0.0330 (19) | 0.0372 (19) | 0.0005 (15) | −0.0010 (15) | −0.0053 (15) |
N4 | 0.049 (2) | 0.0306 (19) | 0.040 (2) | −0.0042 (16) | 0.0057 (17) | −0.0037 (16) |
O1 | 0.062 (3) | 0.060 (3) | 0.118 (4) | −0.026 (2) | −0.019 (3) | 0.033 (3) |
O2 | 0.066 (2) | 0.0470 (19) | 0.062 (2) | −0.0179 (16) | 0.0163 (17) | −0.0116 (16) |
O3 | 0.070 (2) | 0.0442 (18) | 0.0490 (19) | −0.0088 (16) | 0.0181 (16) | −0.0077 (15) |
O11 | 0.0342 (16) | 0.0279 (13) | 0.0452 (16) | 0.0075 (12) | −0.0005 (12) | 0.0031 (12) |
O12 | 0.0386 (17) | 0.0358 (15) | 0.0497 (17) | −0.0106 (13) | −0.0050 (13) | −0.0025 (13) |
O13 | 0.068 (2) | 0.0336 (15) | 0.0260 (15) | −0.0047 (13) | 0.0046 (13) | 0.0024 (11) |
O21 | 0.103 (3) | 0.0358 (17) | 0.060 (2) | 0.0274 (17) | −0.0051 (19) | −0.0033 (15) |
O22 | 0.0496 (19) | 0.061 (2) | 0.062 (2) | −0.0066 (16) | −0.0070 (16) | −0.0232 (15) |
O23 | 0.058 (2) | 0.069 (2) | 0.087 (2) | −0.0283 (18) | 0.0502 (18) | −0.0321 (18) |
C1 | 0.030 (2) | 0.023 (2) | 0.031 (2) | −0.0037 (17) | −0.0006 (18) | 0.0004 (16) |
C2 | 0.029 (2) | 0.030 (2) | 0.041 (2) | −0.0026 (17) | 0.0016 (19) | 0.0018 (19) |
C3 | 0.031 (2) | 0.030 (2) | 0.041 (2) | 0.0019 (18) | 0.0081 (19) | −0.0084 (17) |
C4 | 0.044 (3) | 0.029 (2) | 0.047 (3) | 0.0028 (19) | 0.009 (2) | 0.0020 (19) |
C5 | 0.042 (3) | 0.026 (2) | 0.040 (2) | 0.0008 (19) | 0.006 (2) | 0.0006 (18) |
C6 | 0.035 (2) | 0.026 (2) | 0.039 (2) | −0.0002 (18) | 0.0056 (19) | −0.0056 (17) |
C7 | 0.070 (3) | 0.030 (2) | 0.039 (3) | −0.007 (2) | 0.015 (2) | 0.002 (2) |
C8 | 0.065 (3) | 0.036 (3) | 0.044 (3) | −0.007 (2) | 0.015 (2) | 0.003 (2) |
C9 | 0.054 (3) | 0.036 (2) | 0.036 (2) | −0.002 (2) | 0.006 (2) | −0.008 (2) |
C10 | 0.038 (2) | 0.021 (2) | 0.037 (2) | 0.0015 (18) | 0.0038 (19) | −0.0068 (17) |
C11 | 0.038 (3) | 0.025 (2) | 0.046 (3) | −0.0014 (19) | −0.003 (2) | −0.0052 (19) |
C11N | 0.060 (3) | 0.050 (3) | 0.048 (3) | 0.001 (2) | −0.003 (2) | 0.002 (2) |
C12 | 0.054 (3) | 0.039 (3) | 0.054 (3) | −0.005 (2) | −0.003 (2) | −0.007 (2) |
C12N | 0.045 (3) | 0.056 (3) | 0.056 (3) | 0.008 (2) | 0.017 (2) | 0.003 (2) |
C13 | 0.074 (4) | 0.038 (3) | 0.064 (3) | 0.000 (2) | 0.001 (3) | −0.018 (2) |
C13N | 0.081 (4) | 0.035 (3) | 0.066 (3) | −0.012 (2) | 0.017 (3) | 0.002 (2) |
C14 | 0.083 (4) | 0.030 (3) | 0.065 (3) | −0.012 (2) | −0.007 (3) | −0.002 (2) |
C15 | 0.067 (3) | 0.032 (3) | 0.054 (3) | −0.009 (2) | 0.004 (2) | 0.004 (2) |
C16 | 0.034 (2) | 0.049 (3) | 0.043 (3) | −0.003 (2) | −0.004 (2) | −0.003 (2) |
C21N | 0.047 (3) | 0.049 (3) | 0.053 (3) | −0.013 (2) | −0.013 (2) | 0.001 (2) |
C22N | 0.039 (3) | 0.062 (3) | 0.049 (3) | 0.002 (2) | 0.008 (2) | −0.005 (2) |
C23N | 0.063 (3) | 0.038 (2) | 0.045 (3) | −0.008 (2) | −0.004 (2) | 0.003 (2) |
C101 | 0.042 (3) | 0.048 (3) | 0.037 (2) | 0.001 (2) | 0.011 (2) | 0.000 (2) |
C102 | 0.051 (3) | 0.034 (2) | 0.042 (3) | −0.004 (2) | 0.006 (2) | 0.0010 (19) |
C103 | 0.042 (3) | 0.039 (2) | 0.037 (2) | −0.005 (2) | 0.005 (2) | 0.0052 (19) |
C104 | 0.037 (3) | 0.043 (3) | 0.041 (3) | −0.005 (2) | 0.006 (2) | −0.003 (2) |
C105 | 0.045 (3) | 0.042 (3) | 0.045 (3) | −0.006 (2) | 0.003 (2) | −0.003 (2) |
C106 | 0.048 (3) | 0.046 (3) | 0.048 (3) | −0.008 (2) | 0.005 (2) | −0.003 (2) |
C107 | 0.056 (3) | 0.047 (3) | 0.042 (3) | −0.009 (2) | −0.001 (2) | 0.003 (2) |
C108 | 0.051 (3) | 0.042 (3) | 0.046 (3) | −0.011 (2) | 0.007 (2) | −0.006 (2) |
C109 | 0.058 (3) | 0.043 (3) | 0.043 (3) | −0.011 (2) | 0.007 (2) | 0.003 (2) |
C110 | 0.054 (3) | 0.042 (3) | 0.052 (3) | −0.009 (2) | 0.007 (2) | −0.002 (2) |
C111 | 0.049 (3) | 0.042 (3) | 0.053 (3) | −0.008 (2) | 0.011 (2) | 0.004 (2) |
C112 | 0.052 (3) | 0.037 (3) | 0.052 (3) | −0.007 (2) | −0.001 (2) | 0.001 (2) |
C113 | 0.063 (3) | 0.044 (3) | 0.057 (3) | −0.006 (2) | 0.002 (3) | 0.011 (2) |
C114 | 0.072 (4) | 0.049 (3) | 0.064 (3) | −0.011 (3) | 0.007 (3) | 0.011 (2) |
C201 | 0.052 (3) | 0.043 (3) | 0.035 (2) | −0.007 (2) | −0.001 (2) | −0.0003 (19) |
C202 | 0.046 (3) | 0.042 (3) | 0.046 (3) | 0.002 (2) | 0.004 (2) | 0.003 (2) |
C203 | 0.051 (3) | 0.046 (3) | 0.040 (3) | 0.000 (2) | 0.000 (2) | 0.008 (2) |
C204 | 0.054 (3) | 0.052 (3) | 0.034 (3) | −0.005 (2) | 0.002 (2) | 0.000 (2) |
C205 | 0.053 (3) | 0.049 (3) | 0.045 (3) | −0.003 (2) | 0.003 (2) | −0.004 (2) |
C206 | 0.053 (3) | 0.044 (3) | 0.050 (3) | −0.005 (2) | 0.003 (2) | −0.002 (2) |
C207 | 0.053 (3) | 0.051 (3) | 0.042 (3) | −0.009 (2) | 0.002 (2) | 0.001 (2) |
C208 | 0.054 (3) | 0.047 (3) | 0.053 (3) | −0.006 (2) | 0.008 (2) | −0.002 (2) |
C209 | 0.053 (3) | 0.046 (3) | 0.048 (3) | −0.003 (2) | 0.002 (2) | −0.001 (2) |
C210 | 0.055 (3) | 0.048 (3) | 0.053 (3) | −0.001 (2) | 0.008 (2) | 0.000 (2) |
C211 | 0.054 (3) | 0.048 (3) | 0.059 (3) | −0.001 (2) | 0.003 (2) | 0.003 (2) |
C212 | 0.050 (3) | 0.049 (3) | 0.052 (3) | 0.003 (2) | 0.009 (2) | −0.002 (2) |
C213 | 0.064 (3) | 0.050 (3) | 0.050 (3) | −0.004 (2) | 0.007 (2) | 0.001 (2) |
C214 | 0.075 (4) | 0.045 (3) | 0.057 (3) | −0.003 (3) | 0.002 (3) | 0.000 (2) |
S1—O11 | 1.452 (2) | C8—C9 | 1.426 (5) |
S1—O12 | 1.462 (3) | C9—C10 | 1.438 (5) |
S1—O13 | 1.475 (2) | C11—C12 | 1.380 (5) |
S1—C1 | 1.805 (3) | C11—C16 | 1.385 (5) |
S2—O21 | 1.449 (3) | C12—C13 | 1.384 (5) |
S2—O22 | 1.449 (3) | C13—C14 | 1.383 (5) |
S2—O23 | 1.463 (3) | C14—C15 | 1.374 (6) |
S2—C3 | 1.763 (4) | C15—C16 | 1.404 (5) |
N1—C11N | 1.479 (5) | C101—C102 | 1.531 (5) |
N1—C12N | 1.483 (5) | C102—C103 | 1.525 (5) |
N1—C13N | 1.514 (5) | C103—C104 | 1.522 (5) |
N1—C101 | 1.531 (4) | C104—C105 | 1.537 (5) |
N2—C21N | 1.499 (4) | C105—C106 | 1.544 (5) |
N2—C22N | 1.501 (5) | C106—C107 | 1.538 (5) |
N2—C23N | 1.508 (4) | C107—C108 | 1.521 (5) |
N2—C201 | 1.529 (4) | C108—C109 | 1.544 (5) |
N3—N4 | 1.300 (4) | C109—C110 | 1.535 (5) |
N3—C10 | 1.355 (4) | C110—C111 | 1.531 (5) |
N4—H4 | 1.007 (10) | C111—C112 | 1.528 (5) |
N4—C11 | 1.421 (4) | C112—C113 | 1.527 (5) |
O1—H12 | 0.902 (10) | C113—C114 | 1.547 (5) |
O1—H11 | 0.905 (10) | C201—C202 | 1.513 (5) |
O2—H22 | 0.895 (10) | C202—C203 | 1.536 (5) |
O2—H21 | 0.899 (10) | C203—C204 | 1.541 (5) |
O3—C9 | 1.283 (4) | C204—C205 | 1.532 (5) |
C1—C2 | 1.388 (5) | C205—C206 | 1.548 (5) |
C1—C6 | 1.435 (4) | C206—C207 | 1.539 (5) |
C2—C3 | 1.403 (5) | C207—C208 | 1.525 (5) |
C3—C4 | 1.379 (4) | C208—C209 | 1.526 (5) |
C4—C5 | 1.399 (5) | C209—C210 | 1.540 (5) |
C5—C6 | 1.433 (5) | C210—C211 | 1.530 (5) |
C5—C7 | 1.443 (5) | C211—C212 | 1.527 (5) |
C6—C10 | 1.445 (5) | C212—C213 | 1.530 (5) |
C7—C8 | 1.340 (5) | C213—C214 | 1.536 (5) |
O11—S1—O12 | 115.43 (16) | C1—C6—C10 | 126.7 (3) |
O11—S1—O13 | 111.83 (15) | C8—C7—C5 | 122.5 (4) |
O12—S1—O13 | 111.36 (15) | C7—C8—C9 | 120.4 (4) |
O11—S1—C1 | 105.85 (15) | O3—C9—C8 | 119.0 (4) |
O12—S1—C1 | 107.17 (16) | O3—C9—C10 | 121.9 (3) |
O13—S1—C1 | 104.31 (16) | C8—C9—C10 | 119.1 (4) |
O21—S2—O22 | 113.11 (19) | N3—C10—C9 | 122.4 (3) |
O21—S2—O23 | 114.52 (19) | N3—C10—C6 | 116.4 (3) |
O22—S2—O23 | 111.84 (18) | C9—C10—C6 | 120.9 (3) |
O21—S2—C3 | 105.42 (18) | C12—C11—C16 | 122.3 (4) |
O22—S2—C3 | 105.90 (18) | C12—C11—N4 | 115.8 (4) |
O23—S2—C3 | 105.08 (18) | C16—C11—N4 | 121.8 (4) |
C11N—N1—C12N | 109.5 (3) | C11—C12—C13 | 118.6 (4) |
C11N—N1—C13N | 108.3 (3) | C14—C13—C12 | 119.7 (4) |
C12N—N1—C13N | 109.2 (3) | C15—C14—C13 | 122.0 (4) |
C11N—N1—C101 | 110.9 (3) | C14—C15—C16 | 118.8 (4) |
C12N—N1—C101 | 111.5 (3) | C11—C16—C15 | 118.6 (4) |
C13N—N1—C101 | 107.3 (3) | C102—C101—N1 | 114.1 (3) |
C21N—N2—C22N | 109.3 (3) | C103—C102—C101 | 110.8 (3) |
C21N—N2—C23N | 108.8 (3) | C104—C103—C102 | 110.7 (3) |
C22N—N2—C23N | 109.1 (3) | C103—C104—C105 | 112.5 (3) |
C21N—N2—C201 | 112.0 (3) | C104—C105—C106 | 112.3 (3) |
C22N—N2—C201 | 110.9 (3) | C107—C106—C105 | 112.5 (3) |
C23N—N2—C201 | 106.7 (3) | C108—C107—C106 | 113.4 (3) |
N4—N3—C10 | 116.4 (3) | C107—C108—C109 | 112.7 (3) |
H4—N4—N3 | 125 (2) | C110—C109—C108 | 112.9 (3) |
H4—N4—C11 | 114 (2) | C111—C110—C109 | 111.8 (3) |
N3—N4—C11 | 119.9 (3) | C112—C111—C110 | 113.9 (3) |
H12—O1—H11 | 107.6 (16) | C113—C112—C111 | 111.9 (3) |
H22—O2—H21 | 109.4 (16) | C112—C113—C114 | 113.1 (4) |
C2—C1—C6 | 119.7 (3) | C202—C201—N2 | 115.2 (3) |
C2—C1—S1 | 113.4 (3) | C201—C202—C203 | 108.9 (3) |
C6—C1—S1 | 126.8 (3) | C202—C203—C204 | 110.8 (3) |
C1—C2—C3 | 123.1 (3) | C205—C204—C203 | 111.9 (3) |
C4—C3—C2 | 118.0 (3) | C204—C205—C206 | 112.1 (3) |
C4—C3—S2 | 120.7 (3) | C207—C206—C205 | 112.7 (3) |
C2—C3—S2 | 121.3 (3) | C208—C207—C206 | 113.0 (3) |
C3—C4—C5 | 120.8 (3) | C207—C208—C209 | 112.4 (3) |
C4—C5—C6 | 122.0 (3) | C208—C209—C210 | 112.6 (3) |
C4—C5—C7 | 118.5 (3) | C211—C210—C209 | 113.6 (4) |
C6—C5—C7 | 119.5 (4) | C212—C211—C210 | 113.0 (4) |
C5—C6—C1 | 116.0 (3) | C211—C212—C213 | 113.1 (3) |
C5—C6—C10 | 117.2 (3) | C212—C213—C214 | 111.7 (4) |
C10—N3—N4—H4 | −12 (2) | C1—C6—C10—C9 | −170.6 (4) |
C10—N3—N4—C11 | −178.4 (3) | H4—N4—C11—C12 | 11 (2) |
O11—S1—C1—C2 | −133.7 (3) | N3—N4—C11—C12 | 179.4 (4) |
O12—S1—C1—C2 | 102.6 (3) | H4—N4—C11—C16 | −171 (2) |
O13—S1—C1—C2 | −15.6 (3) | N3—N4—C11—C16 | −2.8 (5) |
O11—S1—C1—C6 | 43.6 (4) | C16—C11—C12—C13 | 0.6 (7) |
O12—S1—C1—C6 | −80.1 (4) | N4—C11—C12—C13 | 178.5 (4) |
O13—S1—C1—C6 | 161.7 (3) | C11—C12—C13—C14 | 0.0 (7) |
C6—C1—C2—C3 | −2.4 (6) | C12—C13—C14—C15 | −0.4 (7) |
S1—C1—C2—C3 | 175.0 (3) | C13—C14—C15—C16 | 0.3 (7) |
C1—C2—C3—C4 | −1.5 (6) | C12—C11—C16—C15 | −0.7 (6) |
C1—C2—C3—S2 | 179.5 (3) | N4—C11—C16—C15 | −178.5 (4) |
O21—S2—C3—C4 | 26.5 (4) | C14—C15—C16—C11 | 0.3 (6) |
O22—S2—C3—C4 | −93.6 (3) | C11N—N1—C101—C102 | −63.2 (4) |
O23—S2—C3—C4 | 147.9 (3) | C12N—N1—C101—C102 | 59.1 (4) |
O21—S2—C3—C2 | −154.6 (3) | C13N—N1—C101—C102 | 178.7 (4) |
O22—S2—C3—C2 | 85.3 (3) | N1—C101—C102—C103 | 178.3 (3) |
O23—S2—C3—C2 | −33.2 (4) | C101—C102—C103—C104 | 179.3 (4) |
C2—C3—C4—C5 | 1.2 (6) | C102—C103—C104—C105 | 179.0 (3) |
S2—C3—C4—C5 | −179.8 (3) | C103—C104—C105—C106 | −179.2 (4) |
C3—C4—C5—C6 | 3.1 (6) | C104—C105—C106—C107 | 173.5 (4) |
C3—C4—C5—C7 | −179.0 (4) | C105—C106—C107—C108 | 171.3 (4) |
C4—C5—C6—C1 | −6.8 (6) | C106—C107—C108—C109 | 177.1 (4) |
C7—C5—C6—C1 | 175.4 (4) | C107—C108—C109—C110 | 177.6 (4) |
C4—C5—C6—C10 | 176.4 (4) | C108—C109—C110—C111 | −178.7 (4) |
C7—C5—C6—C10 | −1.4 (5) | C109—C110—C111—C112 | 178.8 (4) |
C2—C1—C6—C5 | 6.4 (5) | C110—C111—C112—C113 | 178.0 (4) |
S1—C1—C6—C5 | −170.7 (3) | C111—C112—C113—C114 | −179.4 (4) |
C2—C1—C6—C10 | −177.2 (4) | C21N—N2—C201—C202 | −66.4 (4) |
S1—C1—C6—C10 | 5.7 (6) | C22N—N2—C201—C202 | 56.0 (5) |
C4—C5—C7—C8 | 177.9 (4) | C23N—N2—C201—C202 | 174.7 (3) |
C6—C5—C7—C8 | −4.2 (7) | N2—C201—C202—C203 | 165.4 (3) |
C5—C7—C8—C9 | 5.3 (7) | C201—C202—C203—C204 | −177.8 (4) |
C7—C8—C9—O3 | 178.6 (4) | C202—C203—C204—C205 | 171.9 (4) |
C7—C8—C9—C10 | −0.7 (7) | C203—C204—C205—C206 | −174.7 (4) |
N4—N3—C10—C9 | 10.3 (5) | C204—C205—C206—C207 | 173.1 (4) |
N4—N3—C10—C6 | −176.3 (3) | C205—C206—C207—C208 | 177.3 (4) |
O3—C9—C10—N3 | −11.1 (6) | C206—C207—C208—C209 | 177.0 (4) |
C8—C9—C10—N3 | 168.3 (4) | C207—C208—C209—C210 | −177.8 (4) |
O3—C9—C10—C6 | 175.8 (4) | C208—C209—C210—C211 | −177.9 (4) |
C8—C9—C10—C6 | −4.9 (6) | C209—C210—C211—C212 | 178.4 (4) |
C5—C6—C10—N3 | −167.8 (4) | C210—C211—C212—C213 | −178.2 (4) |
C1—C6—C10—N3 | 15.8 (6) | C211—C212—C213—C214 | 179.6 (4) |
C5—C6—C10—C9 | 5.8 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O3 | 1.01 (1) | 1.73 (3) | 2.480 (4) | 128 (3) |
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