Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805012237/hb6180sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805012237/hb6180Isup2.hkl |
CCDC reference: 249472
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.004 Å
- R factor = 0.036
- wR factor = 0.106
- Data-to-parameter ratio = 12.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.55 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.59 PLAT420_ALERT_2_C D-H Without Acceptor N4A - H4B ... ? PLAT420_ALERT_2_C D-H Without Acceptor N4B - H42B ... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990); software used to prepare material for publication: PLATON.
C12H14ClN4+·C7H5O6S−·H2O | F(000) = 2016 |
Mr = 484.92 | Dx = 1.508 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 15.2350 (15) Å | θ = 11.3–13.8° |
b = 19.3290 (12) Å | µ = 0.33 mm−1 |
c = 15.8750 (14) Å | T = 273 K |
β = 113.960 (6)° | Block, colourless |
V = 4272.0 (7) Å3 | 0.30 × 0.25 × 0.12 mm |
Z = 8 |
MACH3 single-crystal diffractometer | 4891 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.013 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
ω–2θ scans | h = −18→16 |
Absorption correction: ψ scan (North et al., 1968) | k = −1→22 |
Tmin = 0.939, Tmax = 0.959 | l = −1→18 |
8317 measured reflections | 3 standard reflections every 60 min |
7493 independent reflections | intensity decay: 3% |
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)] = 0.036 | Hydrogen site location: geom and difmap |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0512P)2 + 1.7056P] where P = (Fo2 + 2Fc2)/3 |
7493 reflections | (Δ/σ)max = 0.041 |
583 parameters | Δρmax = 0.20 e Å−3 |
3 restraints | Δρmin = −0.30 e Å−3 |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | ||
Cl1A | 0.53687 (7) | −0.02379 (6) | −0.14346 (6) | 0.0895 (4) | |
N1A | 0.94831 (14) | 0.05468 (11) | 0.36215 (13) | 0.0357 (7) | |
N2A | 0.97735 (15) | 0.09162 (12) | 0.50795 (14) | 0.0419 (8) | |
N3A | 0.82484 (14) | 0.10253 (11) | 0.39525 (14) | 0.0360 (7) | |
N4A | 0.67496 (15) | 0.11300 (13) | 0.28176 (16) | 0.0519 (9) | |
C2A | 0.91565 (17) | 0.08355 (13) | 0.42101 (16) | 0.0324 (8) | |
C4A | 0.76465 (17) | 0.09162 (13) | 0.30674 (17) | 0.0347 (8) | |
C5A | 0.79425 (17) | 0.05781 (13) | 0.24250 (16) | 0.0356 (8) | |
C6A | 0.88823 (17) | 0.03926 (13) | 0.27276 (17) | 0.0349 (8) | |
C7A | 0.9347 (2) | 0.00337 (15) | 0.21735 (19) | 0.0471 (10) | |
C8A | 0.9952 (3) | 0.0512 (2) | 0.1886 (2) | 0.0769 (14) | |
C9A | 0.72409 (17) | 0.03913 (14) | 0.14738 (17) | 0.0377 (8) | |
C10A | 0.6883 (2) | 0.08819 (16) | 0.07809 (19) | 0.0505 (10) | |
C11A | 0.6294 (2) | 0.06887 (18) | −0.01108 (19) | 0.0571 (10) | |
C12A | 0.6059 (2) | 0.00108 (19) | −0.03023 (19) | 0.0529 (10) | |
C13A | 0.6376 (2) | −0.04850 (18) | 0.0374 (2) | 0.0574 (11) | |
C14A | 0.6964 (2) | −0.02910 (16) | 0.1261 (2) | 0.0515 (10) | |
Cl1B | 0.35204 (6) | 0.51266 (5) | 0.46041 (5) | 0.0693 (3) | |
N1B | −0.03756 (13) | 0.36502 (11) | −0.02113 (13) | 0.0347 (7) | |
N2B | −0.06301 (14) | 0.34015 (12) | −0.17127 (14) | 0.0404 (7) | |
N3B | 0.09149 (13) | 0.35764 (10) | −0.06531 (13) | 0.0318 (7) | |
N4B | 0.24358 (14) | 0.37516 (12) | 0.04198 (14) | 0.0432 (8) | |
C2B | −0.00196 (17) | 0.35413 (12) | −0.08587 (16) | 0.0309 (8) | |
C4B | 0.15012 (16) | 0.37408 (12) | 0.02183 (16) | 0.0299 (8) | |
C5B | 0.11548 (16) | 0.39086 (13) | 0.09056 (16) | 0.0310 (8) | |
C6B | 0.01960 (16) | 0.38418 (13) | 0.06701 (16) | 0.0317 (8) | |
C7B | −0.03125 (18) | 0.40001 (14) | 0.12807 (17) | 0.0392 (9) | |
C8B | −0.0719 (2) | 0.47196 (16) | 0.1132 (2) | 0.0596 (12) | |
C9B | 0.18037 (16) | 0.41929 (13) | 0.18274 (16) | 0.0316 (8) | |
C10B | 0.20430 (19) | 0.48856 (14) | 0.19109 (17) | 0.0430 (9) | |
C11B | 0.2575 (2) | 0.51767 (15) | 0.27600 (18) | 0.0481 (10) | |
C12B | 0.28642 (18) | 0.47656 (15) | 0.35269 (16) | 0.0390 (9) | |
C13B | 0.26557 (19) | 0.40744 (15) | 0.34650 (17) | 0.0440 (9) | |
C14B | 0.21304 (18) | 0.37849 (14) | 0.26125 (17) | 0.0401 (9) | |
S1 | 0.22679 (4) | 0.20183 (4) | 0.40074 (4) | 0.0329 (2) | |
O1C | −0.16861 (12) | 0.27869 (11) | 0.33613 (12) | 0.0553 (7) | |
O2C | −0.21380 (12) | 0.25975 (12) | 0.15943 (12) | 0.0539 (7) | |
O3C | −0.10011 (12) | 0.22455 (11) | 0.11594 (12) | 0.0504 (7) | |
O4C | 0.23097 (12) | 0.18781 (12) | 0.31353 (12) | 0.0572 (7) | |
O5C | 0.28170 (12) | 0.26253 (10) | 0.44603 (12) | 0.0448 (6) | |
O6C | 0.25639 (12) | 0.14254 (10) | 0.46282 (12) | 0.0461 (6) | |
C15C | −0.08015 (17) | 0.25897 (14) | 0.34718 (17) | 0.0377 (8) | |
C16C | −0.05682 (16) | 0.24065 (13) | 0.27368 (16) | 0.0306 (8) | |
C17C | 0.03750 (16) | 0.22213 (12) | 0.29075 (16) | 0.0293 (7) | |
C18C | 0.10668 (15) | 0.22089 (12) | 0.37966 (15) | 0.0275 (7) | |
C19C | 0.08290 (17) | 0.23830 (14) | 0.45299 (16) | 0.0355 (8) | |
C20C | −0.00903 (17) | 0.25723 (15) | 0.43694 (17) | 0.0415 (9) | |
C21C | −0.13100 (17) | 0.24227 (14) | 0.17841 (16) | 0.0353 (8) | |
S1' | 0.54195 (4) | 0.30120 (4) | 0.22338 (4) | 0.0322 (2) | |
O1D | 0.60540 (12) | 0.31566 (11) | 0.61474 (11) | 0.0501 (7) | |
O2D | 0.78522 (12) | 0.29390 (12) | 0.65774 (12) | 0.0574 (8) | |
O3D | 0.84116 (11) | 0.28657 (10) | 0.54965 (11) | 0.0432 (6) | |
O4D | 0.51241 (12) | 0.22906 (9) | 0.20020 (11) | 0.0399 (6) | |
O5D | 0.63050 (12) | 0.31695 (11) | 0.21477 (12) | 0.0509 (7) | |
O6D | 0.46340 (12) | 0.34788 (10) | 0.17242 (11) | 0.0437 (6) | |
C15D | 0.59641 (17) | 0.31423 (14) | 0.52697 (16) | 0.0349 (8) | |
C16D | 0.67398 (15) | 0.30398 (13) | 0.50242 (15) | 0.0282 (7) | |
C17D | 0.65751 (15) | 0.30203 (12) | 0.40912 (15) | 0.0280 (7) | |
C18D | 0.56568 (16) | 0.31041 (13) | 0.34170 (15) | 0.0296 (8) | |
C19D | 0.48965 (17) | 0.32228 (14) | 0.36715 (17) | 0.0385 (8) | |
C20D | 0.50476 (17) | 0.32450 (16) | 0.45830 (17) | 0.0426 (9) | |
C21D | 0.77091 (17) | 0.29456 (14) | 0.57648 (16) | 0.0329 (8) | |
O1W | 0.19039 (15) | 0.09007 (11) | 0.61402 (16) | 0.0655 (8) | |
O2W | 0.14433 (14) | 0.02199 (11) | 0.43180 (16) | 0.0627 (8) | |
H1A | 1.00850 | 0.04550 | 0.38110 | 0.0430* | |
H2A | 0.95840 | 0.10900 | 0.54750 | 0.0500* | |
H2B | 1.03630 | 0.07940 | 0.52470 | 0.0500* | |
H4A | 0.65800 | 0.13240 | 0.32150 | 0.0620* | |
H4B | 0.63370 | 0.10730 | 0.22600 | 0.0620* | |
H7A | 0.88510 | −0.01680 | 0.16280 | 0.0570* | |
H7B | 0.97470 | −0.03400 | 0.25380 | 0.0570* | |
H8A | 0.95520 | 0.08670 | 0.14930 | 0.0920* | |
H8B | 1.02520 | 0.02550 | 0.15570 | 0.0920* | |
H8C | 1.04370 | 0.07200 | 0.24220 | 0.0920* | |
H10A | 0.70400 | 0.13460 | 0.09160 | 0.0610* | |
H11A | 0.60610 | 0.10190 | −0.05750 | 0.0690* | |
H13A | 0.61970 | −0.09450 | 0.02360 | 0.0690* | |
H14A | 0.71770 | −0.06240 | 0.17230 | 0.0620* | |
H1B | −0.09810 | 0.35960 | −0.03620 | 0.0420* | |
H10B | 0.18420 | 0.51610 | 0.13860 | 0.0520* | |
H11B | 0.27350 | 0.56440 | 0.28100 | 0.0580* | |
H13B | 0.28650 | 0.38020 | 0.39930 | 0.0530* | |
H14B | 0.19960 | 0.33140 | 0.25650 | 0.0480* | |
H21A | −0.04210 | 0.33320 | −0.21340 | 0.0480* | |
H22B | −0.12360 | 0.33790 | −0.18460 | 0.0480* | |
H41A | 0.26410 | 0.36570 | 0.00020 | 0.0520* | |
H42B | 0.28360 | 0.38540 | 0.09690 | 0.0520* | |
H71A | 0.01340 | 0.39490 | 0.19200 | 0.0470* | |
H72B | −0.08300 | 0.36710 | 0.11610 | 0.0470* | |
H81A | −0.02030 | 0.50490 | 0.13360 | 0.0710* | |
H82B | −0.11070 | 0.47820 | 0.14760 | 0.0710* | |
H83C | −0.11070 | 0.47880 | 0.04880 | 0.0710* | |
H1C | −0.20450 | 0.27740 | 0.28120 | 0.0660* | |
H3C | −0.14440 | 0.22680 | 0.06480 | 0.0610* | |
H17C | 0.05370 | 0.21060 | 0.24200 | 0.0350* | |
H19C | 0.12960 | 0.23690 | 0.51300 | 0.0430* | |
H20C | −0.02420 | 0.26910 | 0.48620 | 0.0500* | |
H1D | 0.66130 | 0.30760 | 0.64940 | 0.0600* | |
H3D | 0.89240 | 0.28390 | 0.59490 | 0.0520* | |
H17D | 0.70860 | 0.29520 | 0.39220 | 0.0340* | |
H19D | 0.42810 | 0.32870 | 0.32190 | 0.0460* | |
H20D | 0.45340 | 0.33300 | 0.47440 | 0.0510* | |
H11W | 0.17970 | 0.11800 | 0.65400 | 0.0790* | |
H12W | 0.22120 | 0.11590 | 0.58770 | 0.0790* | |
H21W | 0.18060 | 0.06050 | 0.42220 | 0.0750* | |
H22W | 0.17750 | 0.00220 | 0.49360 | 0.0750* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1A | 0.0680 (6) | 0.1414 (10) | 0.0415 (5) | −0.0247 (6) | 0.0041 (4) | −0.0343 (5) |
N1A | 0.0277 (11) | 0.0474 (14) | 0.0297 (11) | 0.0017 (9) | 0.0093 (9) | −0.0038 (10) |
N2A | 0.0334 (12) | 0.0599 (16) | 0.0280 (11) | −0.0001 (10) | 0.0080 (9) | −0.0070 (10) |
N3A | 0.0285 (11) | 0.0478 (14) | 0.0291 (11) | −0.0013 (10) | 0.0091 (9) | −0.0058 (10) |
N4A | 0.0314 (12) | 0.0793 (19) | 0.0394 (13) | 0.0085 (12) | 0.0085 (10) | −0.0121 (13) |
C2A | 0.0329 (13) | 0.0334 (15) | 0.0303 (13) | −0.0036 (11) | 0.0122 (11) | −0.0014 (11) |
C4A | 0.0324 (13) | 0.0358 (15) | 0.0357 (14) | −0.0014 (11) | 0.0136 (12) | −0.0011 (12) |
C5A | 0.0363 (14) | 0.0386 (16) | 0.0293 (13) | −0.0015 (11) | 0.0105 (11) | −0.0025 (11) |
C6A | 0.0375 (14) | 0.0364 (15) | 0.0307 (13) | −0.0027 (11) | 0.0137 (11) | −0.0024 (11) |
C7A | 0.0460 (16) | 0.0564 (19) | 0.0377 (15) | 0.0048 (14) | 0.0157 (13) | −0.0070 (14) |
C8A | 0.082 (2) | 0.096 (3) | 0.072 (2) | −0.016 (2) | 0.051 (2) | −0.023 (2) |
C9A | 0.0317 (13) | 0.0485 (17) | 0.0294 (13) | −0.0016 (12) | 0.0087 (11) | −0.0047 (12) |
C10A | 0.0500 (17) | 0.0499 (19) | 0.0402 (16) | −0.0045 (14) | 0.0067 (13) | −0.0018 (14) |
C11A | 0.0519 (18) | 0.072 (2) | 0.0322 (15) | 0.0032 (16) | 0.0015 (13) | 0.0020 (15) |
C12A | 0.0388 (16) | 0.081 (2) | 0.0338 (16) | −0.0071 (16) | 0.0095 (13) | −0.0189 (16) |
C13A | 0.0558 (19) | 0.058 (2) | 0.0548 (19) | −0.0162 (16) | 0.0189 (16) | −0.0213 (17) |
C14A | 0.0515 (18) | 0.054 (2) | 0.0409 (16) | −0.0065 (14) | 0.0105 (14) | −0.0048 (14) |
Cl1B | 0.0786 (6) | 0.0828 (6) | 0.0313 (4) | −0.0241 (5) | 0.0067 (4) | −0.0162 (4) |
N1B | 0.0236 (10) | 0.0455 (14) | 0.0316 (11) | −0.0070 (9) | 0.0076 (9) | −0.0067 (10) |
N2B | 0.0292 (11) | 0.0580 (15) | 0.0270 (11) | −0.0022 (10) | 0.0042 (9) | −0.0068 (10) |
N3B | 0.0285 (11) | 0.0355 (12) | 0.0281 (11) | −0.0032 (9) | 0.0080 (9) | −0.0031 (9) |
N4B | 0.0271 (11) | 0.0691 (17) | 0.0315 (12) | −0.0090 (11) | 0.0098 (9) | −0.0126 (11) |
C2B | 0.0317 (13) | 0.0265 (14) | 0.0298 (13) | −0.0024 (10) | 0.0077 (11) | −0.0026 (11) |
C4B | 0.0269 (12) | 0.0311 (14) | 0.0282 (13) | −0.0040 (10) | 0.0077 (10) | −0.0020 (10) |
C5B | 0.0294 (13) | 0.0346 (15) | 0.0262 (12) | −0.0033 (10) | 0.0085 (10) | 0.0007 (11) |
C6B | 0.0301 (13) | 0.0338 (14) | 0.0281 (13) | −0.0064 (11) | 0.0085 (10) | −0.0003 (11) |
C7B | 0.0309 (13) | 0.0524 (18) | 0.0324 (14) | −0.0034 (12) | 0.0108 (11) | −0.0042 (13) |
C8B | 0.064 (2) | 0.059 (2) | 0.058 (2) | 0.0051 (16) | 0.0270 (17) | −0.0078 (16) |
C9B | 0.0250 (12) | 0.0394 (15) | 0.0268 (13) | −0.0023 (11) | 0.0068 (10) | −0.0035 (11) |
C10B | 0.0506 (16) | 0.0429 (17) | 0.0262 (13) | −0.0083 (13) | 0.0059 (12) | 0.0019 (12) |
C11B | 0.0572 (18) | 0.0424 (17) | 0.0364 (16) | −0.0147 (14) | 0.0106 (14) | −0.0062 (13) |
C12B | 0.0337 (14) | 0.0527 (18) | 0.0248 (13) | −0.0074 (12) | 0.0060 (11) | −0.0081 (12) |
C13B | 0.0426 (15) | 0.0511 (19) | 0.0264 (14) | 0.0016 (13) | 0.0019 (12) | 0.0071 (13) |
C14B | 0.0398 (15) | 0.0362 (16) | 0.0368 (15) | −0.0005 (12) | 0.0077 (12) | 0.0006 (12) |
S1 | 0.0202 (3) | 0.0503 (4) | 0.0236 (3) | 0.0022 (3) | 0.0041 (2) | 0.0016 (3) |
O1C | 0.0287 (9) | 0.1014 (17) | 0.0341 (10) | 0.0200 (10) | 0.0110 (8) | 0.0019 (11) |
O2C | 0.0273 (10) | 0.0922 (16) | 0.0340 (10) | 0.0172 (10) | 0.0041 (8) | −0.0008 (10) |
O3C | 0.0323 (10) | 0.0843 (15) | 0.0247 (9) | 0.0186 (10) | 0.0013 (8) | −0.0042 (9) |
O4C | 0.0286 (9) | 0.1109 (18) | 0.0294 (10) | 0.0126 (10) | 0.0091 (8) | −0.0081 (11) |
O5C | 0.0327 (9) | 0.0564 (13) | 0.0334 (10) | −0.0142 (9) | 0.0011 (8) | 0.0071 (9) |
O6C | 0.0317 (9) | 0.0473 (12) | 0.0486 (11) | 0.0097 (8) | 0.0054 (8) | 0.0110 (9) |
C15C | 0.0269 (12) | 0.0515 (17) | 0.0342 (14) | 0.0073 (12) | 0.0119 (11) | 0.0020 (12) |
C16C | 0.0235 (12) | 0.0362 (15) | 0.0284 (13) | 0.0017 (10) | 0.0066 (10) | 0.0033 (11) |
C17C | 0.0275 (12) | 0.0344 (14) | 0.0241 (12) | 0.0027 (10) | 0.0086 (10) | −0.0026 (10) |
C18C | 0.0221 (11) | 0.0313 (14) | 0.0253 (12) | 0.0002 (10) | 0.0056 (10) | 0.0016 (10) |
C19C | 0.0302 (13) | 0.0479 (17) | 0.0237 (12) | 0.0019 (12) | 0.0061 (10) | 0.0018 (12) |
C20C | 0.0341 (14) | 0.0625 (19) | 0.0277 (13) | 0.0106 (13) | 0.0124 (11) | 0.0008 (13) |
C21C | 0.0270 (13) | 0.0448 (17) | 0.0294 (13) | 0.0074 (11) | 0.0067 (11) | 0.0019 (12) |
S1' | 0.0244 (3) | 0.0486 (4) | 0.0195 (3) | −0.0013 (3) | 0.0048 (2) | 0.0043 (3) |
O1D | 0.0343 (10) | 0.0926 (16) | 0.0247 (9) | 0.0020 (10) | 0.0133 (8) | −0.0031 (10) |
O2D | 0.0337 (10) | 0.1144 (19) | 0.0190 (9) | 0.0050 (11) | 0.0054 (8) | −0.0034 (10) |
O3D | 0.0249 (9) | 0.0787 (14) | 0.0216 (9) | 0.0068 (9) | 0.0049 (7) | 0.0069 (9) |
O4D | 0.0397 (10) | 0.0484 (12) | 0.0263 (9) | −0.0001 (8) | 0.0079 (8) | −0.0021 (8) |
O5D | 0.0327 (10) | 0.0913 (16) | 0.0295 (10) | −0.0078 (10) | 0.0133 (8) | 0.0069 (10) |
O6D | 0.0378 (10) | 0.0565 (13) | 0.0265 (9) | 0.0066 (9) | 0.0025 (8) | 0.0106 (8) |
C15D | 0.0359 (14) | 0.0454 (16) | 0.0233 (12) | −0.0029 (12) | 0.0120 (11) | −0.0014 (11) |
C16D | 0.0252 (11) | 0.0355 (14) | 0.0209 (11) | −0.0035 (10) | 0.0064 (9) | −0.0026 (10) |
C17D | 0.0242 (11) | 0.0340 (14) | 0.0240 (12) | −0.0020 (10) | 0.0079 (10) | −0.0010 (10) |
C18D | 0.0276 (12) | 0.0361 (15) | 0.0219 (12) | −0.0021 (10) | 0.0067 (10) | 0.0026 (10) |
C19D | 0.0265 (12) | 0.0580 (18) | 0.0267 (13) | 0.0023 (12) | 0.0063 (11) | 0.0005 (12) |
C20D | 0.0263 (13) | 0.071 (2) | 0.0318 (14) | 0.0036 (13) | 0.0131 (11) | −0.0011 (13) |
C21D | 0.0298 (12) | 0.0459 (16) | 0.0212 (13) | 0.0005 (11) | 0.0084 (10) | −0.0028 (11) |
O1W | 0.0715 (15) | 0.0596 (14) | 0.0753 (15) | −0.0042 (12) | 0.0401 (13) | −0.0120 (12) |
O2W | 0.0432 (11) | 0.0616 (14) | 0.0790 (16) | 0.0005 (10) | 0.0203 (11) | 0.0096 (12) |
Cl1A—C12A | 1.741 (3) | C10A—C11A | 1.384 (4) |
Cl1B—C12B | 1.738 (3) | C11A—C12A | 1.360 (5) |
S1—O5C | 1.451 (2) | C12A—C13A | 1.372 (5) |
S1—O6C | 1.458 (2) | C13A—C14A | 1.379 (4) |
S1—C18C | 1.760 (3) | C7A—H7A | 0.9703 |
S1—O4C | 1.4373 (19) | C7A—H7B | 0.9703 |
S1'—O4D | 1.4655 (19) | C8A—H8B | 0.9604 |
S1'—O5D | 1.443 (2) | C8A—H8A | 0.9605 |
S1'—C18D | 1.772 (2) | C8A—H8C | 0.9597 |
S1'—O6D | 1.454 (2) | C10A—H10A | 0.9307 |
O1C—C15C | 1.342 (3) | C11A—H11A | 0.9296 |
O2C—C21C | 1.220 (3) | C13A—H13A | 0.9297 |
O3C—C21C | 1.304 (3) | C14A—H14A | 0.9296 |
O1C—H1C | 0.8202 | C4B—C5B | 1.429 (4) |
O3C—H3C | 0.8194 | C5B—C9B | 1.499 (3) |
O1D—C15D | 1.344 (3) | C5B—C6B | 1.359 (4) |
O2D—C21D | 1.218 (3) | C6B—C7B | 1.498 (4) |
O3D—C21D | 1.312 (3) | C7B—C8B | 1.502 (4) |
O1D—H1D | 0.8196 | C9B—C14B | 1.385 (3) |
O3D—H3D | 0.8201 | C9B—C10B | 1.380 (4) |
O1W—H11W | 0.8971 | C10B—C11B | 1.380 (4) |
O1W—H12W | 0.8964 | C11B—C12B | 1.368 (4) |
N1A—C6A | 1.373 (3) | C12B—C13B | 1.368 (4) |
N1A—C2A | 1.345 (3) | C13B—C14B | 1.380 (4) |
N2A—C2A | 1.326 (3) | C7B—H72B | 0.9699 |
N3A—C2A | 1.325 (4) | C7B—H71A | 0.9704 |
N3A—C4A | 1.347 (3) | C8B—H83C | 0.9598 |
N4A—C4A | 1.325 (4) | C8B—H82B | 0.9614 |
N1A—H1A | 0.8595 | C8B—H81A | 0.9599 |
N2A—H2A | 0.8589 | C10B—H10B | 0.9296 |
N2A—H2B | 0.8597 | C11B—H11B | 0.9305 |
O2W—H21W | 0.9752 | C13B—H13B | 0.9297 |
O2W—H22W | 0.9806 | C14B—H14B | 0.9293 |
N4A—H4A | 0.8589 | C15C—C20C | 1.397 (4) |
N4A—H4B | 0.8596 | C15C—C16C | 1.396 (4) |
N1B—C2B | 1.359 (3) | C16C—C21C | 1.476 (3) |
N1B—C6B | 1.365 (3) | C16C—C17C | 1.396 (4) |
N2B—C2B | 1.324 (3) | C17C—C18C | 1.377 (3) |
N3B—C2B | 1.327 (3) | C18C—C19C | 1.394 (3) |
N3B—C4B | 1.345 (3) | C19C—C20C | 1.368 (4) |
N4B—C4B | 1.327 (3) | C17C—H17C | 0.9299 |
N1B—H1B | 0.8600 | C19C—H19C | 0.9295 |
N2B—H21A | 0.8602 | C20C—H20C | 0.9297 |
N2B—H22B | 0.8603 | C15D—C16D | 1.401 (4) |
N4B—H41A | 0.8599 | C15D—C20D | 1.393 (4) |
N4B—H42B | 0.8598 | C16D—C21D | 1.479 (3) |
C4A—C5A | 1.430 (4) | C16D—C17D | 1.399 (3) |
C5A—C6A | 1.360 (4) | C17D—C18D | 1.383 (3) |
C5A—C9A | 1.497 (3) | C18D—C19D | 1.392 (4) |
C6A—C7A | 1.504 (4) | C19D—C20D | 1.370 (4) |
C7A—C8A | 1.501 (5) | C17D—H17D | 0.9302 |
C9A—C10A | 1.385 (4) | C19D—H19D | 0.9293 |
C9A—C14A | 1.384 (4) | C20D—H20D | 0.9311 |
O6C—S1—C18C | 107.77 (11) | N1B—C2B—N3B | 121.6 (2) |
O4C—S1—O6C | 112.35 (13) | N3B—C4B—C5B | 122.8 (2) |
O4C—S1—C18C | 107.79 (11) | N3B—C4B—N4B | 116.8 (2) |
O4C—S1—O5C | 112.81 (12) | N4B—C4B—C5B | 120.4 (2) |
O5C—S1—C18C | 105.70 (12) | C6B—C5B—C9B | 120.8 (2) |
O5C—S1—O6C | 110.05 (11) | C4B—C5B—C9B | 121.8 (2) |
O5D—S1'—O6D | 113.98 (12) | C4B—C5B—C6B | 117.2 (2) |
O4D—S1'—C18D | 105.75 (11) | N1B—C6B—C5B | 118.3 (2) |
O4D—S1'—O6D | 110.56 (11) | C5B—C6B—C7B | 125.7 (2) |
O5D—S1'—C18D | 106.45 (12) | N1B—C6B—C7B | 115.9 (2) |
O4D—S1'—O5D | 112.37 (12) | C6B—C7B—C8B | 112.1 (2) |
O6D—S1'—C18D | 107.16 (11) | C10B—C9B—C14B | 118.8 (2) |
C15C—O1C—H1C | 109.32 | C5B—C9B—C14B | 121.6 (2) |
C21C—O3C—H3C | 109.46 | C5B—C9B—C10B | 119.6 (2) |
C15D—O1D—H1D | 109.44 | C9B—C10B—C11B | 121.1 (2) |
C21D—O3D—H3D | 109.57 | C10B—C11B—C12B | 118.8 (3) |
H11W—O1W—H12W | 105.93 | Cl1B—C12B—C11B | 119.4 (2) |
C2A—N1A—C6A | 121.9 (2) | C11B—C12B—C13B | 121.5 (2) |
C2A—N3A—C4A | 117.5 (2) | Cl1B—C12B—C13B | 119.13 (19) |
C2A—N1A—H1A | 119.04 | C12B—C13B—C14B | 119.5 (2) |
C6A—N1A—H1A | 119.05 | C9B—C14B—C13B | 120.3 (2) |
C2A—N2A—H2A | 120.01 | H71A—C7B—H72B | 107.88 |
C2A—N2A—H2B | 119.96 | C6B—C7B—H72B | 109.40 |
H2A—N2A—H2B | 120.03 | C8B—C7B—H72B | 109.03 |
H21W—O2W—H22W | 111.08 | C8B—C7B—H71A | 109.14 |
H4A—N4A—H4B | 120.00 | C6B—C7B—H71A | 109.20 |
C4A—N4A—H4B | 120.15 | H81A—C8B—H83C | 109.49 |
C4A—N4A—H4A | 119.85 | H82B—C8B—H83C | 109.45 |
C2B—N1B—C6B | 122.2 (2) | C7B—C8B—H81A | 109.41 |
C2B—N3B—C4B | 117.6 (2) | C7B—C8B—H83C | 109.35 |
C6B—N1B—H1B | 118.93 | C7B—C8B—H82B | 109.66 |
C2B—N1B—H1B | 118.88 | H81A—C8B—H82B | 109.47 |
H21A—N2B—H22B | 120.00 | C9B—C10B—H10B | 119.44 |
C2B—N2B—H22B | 119.98 | C11B—C10B—H10B | 119.42 |
C2B—N2B—H21A | 120.01 | C12B—C11B—H11B | 120.62 |
H41A—N4B—H42B | 120.06 | C10B—C11B—H11B | 120.59 |
C4B—N4B—H41A | 120.09 | C12B—C13B—H13B | 120.26 |
C4B—N4B—H42B | 119.85 | C14B—C13B—H13B | 120.29 |
N1A—C2A—N2A | 117.8 (2) | C13B—C14B—H14B | 119.84 |
N2A—C2A—N3A | 119.9 (2) | C9B—C14B—H14B | 119.85 |
N1A—C2A—N3A | 122.3 (2) | C16C—C15C—C20C | 119.4 (3) |
N3A—C4A—C5A | 122.5 (2) | O1C—C15C—C20C | 117.5 (2) |
N3A—C4A—N4A | 116.5 (2) | O1C—C15C—C16C | 123.1 (2) |
N4A—C4A—C5A | 121.0 (2) | C15C—C16C—C21C | 120.1 (2) |
C4A—C5A—C9A | 121.8 (2) | C15C—C16C—C17C | 119.6 (2) |
C4A—C5A—C6A | 117.4 (2) | C17C—C16C—C21C | 120.2 (2) |
C6A—C5A—C9A | 120.7 (2) | C16C—C17C—C18C | 120.2 (2) |
C5A—C6A—C7A | 126.4 (2) | C17C—C18C—C19C | 120.1 (2) |
N1A—C6A—C7A | 115.5 (2) | S1—C18C—C19C | 119.64 (18) |
N1A—C6A—C5A | 118.2 (2) | S1—C18C—C17C | 120.16 (19) |
C6A—C7A—C8A | 112.7 (3) | C18C—C19C—C20C | 120.2 (2) |
C10A—C9A—C14A | 118.4 (2) | C15C—C20C—C19C | 120.5 (2) |
C5A—C9A—C10A | 121.7 (2) | O2C—C21C—O3C | 122.8 (2) |
C5A—C9A—C14A | 119.9 (2) | O3C—C21C—C16C | 114.3 (2) |
C9A—C10A—C11A | 120.7 (3) | O2C—C21C—C16C | 122.9 (2) |
C10A—C11A—C12A | 119.4 (3) | C16C—C17C—H17C | 119.99 |
Cl1A—C12A—C13A | 119.2 (3) | C18C—C17C—H17C | 119.85 |
Cl1A—C12A—C11A | 119.4 (2) | C18C—C19C—H19C | 119.91 |
C11A—C12A—C13A | 121.4 (3) | C20C—C19C—H19C | 119.90 |
C12A—C13A—C14A | 119.0 (3) | C19C—C20C—H20C | 119.66 |
C9A—C14A—C13A | 121.0 (3) | C15C—C20C—H20C | 119.82 |
C6A—C7A—H7B | 108.99 | C16D—C15D—C20D | 119.5 (2) |
H7A—C7A—H7B | 107.82 | O1D—C15D—C20D | 117.1 (2) |
C6A—C7A—H7A | 109.05 | O1D—C15D—C16D | 123.3 (2) |
C8A—C7A—H7A | 109.14 | C15D—C16D—C21D | 118.6 (2) |
C8A—C7A—H7B | 108.98 | C17D—C16D—C21D | 122.0 (2) |
H8A—C8A—H8B | 109.44 | C15D—C16D—C17D | 119.3 (2) |
C7A—C8A—H8C | 109.58 | C16D—C17D—C18D | 120.4 (2) |
H8B—C8A—H8C | 109.50 | S1'—C18D—C17D | 121.03 (19) |
C7A—C8A—H8B | 109.47 | S1'—C18D—C19D | 119.25 (18) |
C7A—C8A—H8A | 109.36 | C17D—C18D—C19D | 119.6 (2) |
H8A—C8A—H8C | 109.49 | C18D—C19D—C20D | 120.6 (2) |
C9A—C10A—H10A | 119.69 | C15D—C20D—C19D | 120.5 (3) |
C11A—C10A—H10A | 119.66 | O2D—C21D—O3D | 121.6 (2) |
C12A—C11A—H11A | 120.23 | O2D—C21D—C16D | 122.3 (2) |
C10A—C11A—H11A | 120.37 | O3D—C21D—C16D | 116.1 (2) |
C14A—C13A—H13A | 120.49 | C18D—C17D—H17D | 119.69 |
C12A—C13A—H13A | 120.47 | C16D—C17D—H17D | 119.89 |
C9A—C14A—H14A | 119.54 | C18D—C19D—H19D | 119.67 |
C13A—C14A—H14A | 119.42 | C20D—C19D—H19D | 119.74 |
N1B—C2B—N2B | 118.4 (2) | C19D—C20D—H20D | 119.72 |
N2B—C2B—N3B | 120.0 (2) | C15D—C20D—H20D | 119.82 |
O6C—S1—C18C—C17C | −123.2 (2) | N4B—C4B—C5B—C6B | −175.7 (2) |
O4C—S1—C18C—C19C | −178.3 (2) | C9B—C5B—C6B—C7B | −3.1 (4) |
O5C—S1—C18C—C19C | −57.5 (2) | C4B—C5B—C9B—C10B | 79.7 (3) |
O6C—S1—C18C—C19C | 60.2 (2) | C6B—C5B—C9B—C10B | −96.0 (3) |
O4C—S1—C18C—C17C | −1.7 (2) | C4B—C5B—C6B—C7B | −179.1 (2) |
O5C—S1—C18C—C17C | 119.1 (2) | C9B—C5B—C6B—N1B | 173.1 (2) |
O6D—S1'—C18D—C17D | −148.3 (2) | C4B—C5B—C6B—N1B | −2.8 (4) |
O4D—S1'—C18D—C17D | 93.8 (2) | C6B—C5B—C9B—C14B | 80.4 (3) |
O5D—S1'—C18D—C17D | −26.0 (2) | C4B—C5B—C9B—C14B | −103.8 (3) |
O6D—S1'—C18D—C19D | 35.5 (2) | N1B—C6B—C7B—C8B | −81.4 (3) |
O4D—S1'—C18D—C19D | −82.5 (2) | C5B—C6B—C7B—C8B | 94.9 (3) |
O5D—S1'—C18D—C19D | 157.8 (2) | C10B—C9B—C14B—C13B | 2.3 (4) |
C6A—N1A—C2A—N3A | −3.9 (4) | C5B—C9B—C14B—C13B | −174.1 (3) |
C2A—N1A—C6A—C5A | 3.9 (4) | C5B—C9B—C10B—C11B | 174.8 (3) |
C2A—N1A—C6A—C7A | −176.6 (2) | C14B—C9B—C10B—C11B | −1.8 (4) |
C6A—N1A—C2A—N2A | 174.8 (2) | C9B—C10B—C11B—C12B | −0.1 (5) |
C2A—N3A—C4A—C5A | 3.1 (4) | C10B—C11B—C12B—Cl1B | −179.1 (2) |
C2A—N3A—C4A—N4A | −177.9 (2) | C10B—C11B—C12B—C13B | 1.5 (5) |
C4A—N3A—C2A—N2A | −178.4 (2) | C11B—C12B—C13B—C14B | −0.9 (5) |
C4A—N3A—C2A—N1A | 0.3 (4) | Cl1B—C12B—C13B—C14B | 179.6 (2) |
C6B—N1B—C2B—N2B | −175.6 (2) | C12B—C13B—C14B—C9B | −1.0 (4) |
C6B—N1B—C2B—N3B | 4.0 (4) | C16C—C15C—C20C—C19C | 0.5 (4) |
C2B—N1B—C6B—C7B | 175.0 (2) | O1C—C15C—C16C—C21C | −0.1 (4) |
C2B—N1B—C6B—C5B | −1.6 (4) | C20C—C15C—C16C—C21C | −179.9 (3) |
C2B—N3B—C4B—N4B | 177.9 (2) | O1C—C15C—C20C—C19C | −179.3 (3) |
C2B—N3B—C4B—C5B | −3.1 (3) | C20C—C15C—C16C—C17C | −1.2 (4) |
C4B—N3B—C2B—N2B | 178.0 (2) | O1C—C15C—C16C—C17C | 178.6 (2) |
C4B—N3B—C2B—N1B | −1.6 (3) | C21C—C16C—C17C—C18C | 179.8 (2) |
N4A—C4A—C5A—C9A | −5.8 (4) | C15C—C16C—C21C—O2C | 0.7 (4) |
N3A—C4A—C5A—C9A | 173.2 (2) | C17C—C16C—C21C—O3C | 0.8 (4) |
N3A—C4A—C5A—C6A | −3.0 (4) | C15C—C16C—C21C—O3C | 179.5 (2) |
N4A—C4A—C5A—C6A | 178.1 (2) | C17C—C16C—C21C—O2C | −178.1 (3) |
C4A—C5A—C9A—C10A | 77.2 (4) | C15C—C16C—C17C—C18C | 1.0 (4) |
C6A—C5A—C9A—C10A | −106.8 (3) | C16C—C17C—C18C—S1 | −176.77 (19) |
C4A—C5A—C9A—C14A | −105.3 (3) | C16C—C17C—C18C—C19C | −0.2 (4) |
C9A—C5A—C6A—C7A | 3.8 (4) | S1—C18C—C19C—C20C | 176.1 (2) |
C4A—C5A—C6A—N1A | −0.6 (4) | C17C—C18C—C19C—C20C | −0.5 (4) |
C6A—C5A—C9A—C14A | 70.7 (4) | C18C—C19C—C20C—C15C | 0.4 (4) |
C4A—C5A—C6A—C7A | 180.0 (2) | C20D—C15D—C16D—C17D | −2.0 (4) |
C9A—C5A—C6A—N1A | −176.7 (2) | C20D—C15D—C16D—C21D | 178.8 (3) |
C5A—C6A—C7A—C8A | 104.8 (3) | O1D—C15D—C20D—C19D | −178.6 (3) |
N1A—C6A—C7A—C8A | −74.7 (3) | O1D—C15D—C16D—C21D | −0.3 (4) |
C5A—C9A—C10A—C11A | 174.9 (3) | C16D—C15D—C20D—C19D | 2.2 (4) |
C5A—C9A—C14A—C13A | −175.1 (3) | O1D—C15D—C16D—C17D | 178.9 (2) |
C10A—C9A—C14A—C13A | 2.5 (5) | C15D—C16D—C17D—C18D | 0.3 (4) |
C14A—C9A—C10A—C11A | −2.6 (5) | C17D—C16D—C21D—O2D | −177.5 (3) |
C9A—C10A—C11A—C12A | 0.7 (5) | C17D—C16D—C21D—O3D | 2.2 (4) |
C10A—C11A—C12A—C13A | 1.5 (5) | C15D—C16D—C21D—O2D | 1.6 (4) |
C10A—C11A—C12A—Cl1A | −176.8 (3) | C21D—C16D—C17D—C18D | 179.4 (2) |
Cl1A—C12A—C13A—C14A | 176.6 (3) | C15D—C16D—C21D—O3D | −178.7 (2) |
C11A—C12A—C13A—C14A | −1.6 (5) | C16D—C17D—C18D—C19D | 1.3 (4) |
C12A—C13A—C14A—C9A | −0.4 (5) | C16D—C17D—C18D—S1' | −174.89 (19) |
N3B—C4B—C5B—C6B | 5.3 (4) | S1'—C18D—C19D—C20D | 175.1 (2) |
N3B—C4B—C5B—C9B | −170.6 (2) | C17D—C18D—C19D—C20D | −1.2 (4) |
N4B—C4B—C5B—C9B | 8.4 (4) | C18D—C19D—C20D—C15D | −0.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O2Wi | 0.86 | 1.95 | 2.803 (3) | 176 |
N1B—H1B···O6Cii | 0.86 | 2.21 | 3.048 (3) | 164 |
O1C—H1C···O2C | 0.82 | 1.91 | 2.628 (3) | 146 |
O1C—H1C···O5Diii | 0.82 | 2.42 | 2.973 (3) | 125 |
O1D—H1D···O2D | 0.82 | 1.86 | 2.575 (3) | 145 |
O1D—H1D···O4Civ | 0.82 | 2.38 | 2.953 (2) | 127 |
N2A—H2A···O6Div | 0.86 | 2.12 | 2.946 (3) | 160 |
N2A—H2B···O1Wi | 0.86 | 2.20 | 2.989 (3) | 152 |
O3C—H3C···O5Cii | 0.82 | 1.77 | 2.576 (3) | 166 |
O3D—H3D···O4Div | 0.82 | 1.93 | 2.747 (2) | 176 |
N4A—H4A···N3Biv | 0.86 | 2.40 | 3.216 (3) | 158 |
O1W—H11W···O5Dv | 0.90 | 1.91 | 2.794 (3) | 167 |
O1W—H12W···O6C | 0.90 | 2.31 | 3.124 (3) | 151 |
N2B—H21A···O4Dii | 0.86 | 2.22 | 3.029 (3) | 156 |
O2W—H21W···O6C | 0.98 | 1.91 | 2.811 (3) | 152 |
N2B—H22B···O2Dvi | 0.86 | 2.47 | 2.901 (3) | 112 |
N2B—H22B···O4Cii | 0.86 | 2.26 | 3.096 (3) | 164 |
O2W—H22W···O1W | 0.98 | 2.50 | 2.991 (3) | 110 |
N4B—H41A···N3Aii | 0.86 | 2.29 | 3.080 (3) | 152 |
C7A—H7B···O6Dvii | 0.97 | 2.56 | 3.507 (3) | 164 |
C13B—H13B···O5C | 0.93 | 2.40 | 3.176 (3) | 141 |
C17C—H17C···O4C | 0.93 | 2.51 | 2.897 (3) | 105 |
C17C—H17C···O1Dii | 0.93 | 2.50 | 3.429 (3) | 177 |
C17D—H17D···O1Ci | 0.93 | 2.40 | 3.325 (3) | 175 |
C19C—H19C···O2Civ | 0.93 | 2.57 | 3.477 (3) | 166 |
Symmetry codes: (i) x+1, y, z; (ii) x−1/2, −y+1/2, z−1/2; (iii) x−1, y, z; (iv) x+1/2, −y+1/2, z+1/2; (v) x−1/2, −y+1/2, z+1/2; (vi) x−1, y, z−1; (vii) −x+3/2, y−1/2, −z+1/2. |
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