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Trimethoprim sulfate trihydrate, 2C
14H
19N
4O
3+·SO
42−·3H
2O [(TMPH
+)
2(SO
4)
2−·3H
2O, TMPH
+ = 2,4-diamino-5-(3,4,5-methoxybenzyl)pyrimidin-1-ium], is an antibacterial agent. In its N1-protonated form, it inhibits the bacterial dihydrofolate reductase enzyme. The asymmetric unit contains two TMPH cations, a sulfate anion and three water molecules. The TMPH cations are each paired about their respective inversion centres
via N—H
N hydrogen bonds. These pairs are further bridged by a network of hydrogen bonds involving the sulfate anion and water molecules. Both the TMPH cations make hydrogen bonds with water molecules through the 2-amino groups, reminiscent of TMP-dihydrofolate reductase complexes. The pyrimidine plane makes a dihedral angle of 75.89 (8)° with the phenyl ring in one TMPH cation, the corresponding angle in the other moiety being 69.96 (8)°.
Supporting information
CCDC reference: 177210
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.036
- wR factor = 0.092
- Data-to-parameter ratio = 9.5
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: MolEN (Fair, 1990); cell refinement: MolEN; data reduction: MolEN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP (Johnson, 1976); software used to prepare material for publication: PLATON (Spek, 1997).
Crystal data top
2C14H19N4O3+·SO4−·3H2O | F(000) = 1552 |
Mr = 732.78 | Dx = 1.438 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
a = 7.229 (1) Å | Cell parameters from 35 reflections |
b = 23.242 (1) Å | θ = 3–70.8° |
c = 20.373 (1) Å | µ = 0.17 mm−1 |
β = 98.59 (1)° | T = 293 K |
V = 3384.6 (5) Å3 | Needle, colourless |
Z = 4 | 0.3 × 0.2 × 0.2 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.014 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 1.3° |
Graphite monochromator | h = 0→8 |
ω–2θ scans | k = 0→27 |
6445 measured reflections | l = −24→23 |
5951 independent reflections | 4 standard reflections every 60 min |
5134 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
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: inferred from neighbouring sites |
wR(F2) = 0.092 | See text |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0402P)2 + 1.9477P] where P = (Fo2 + 2Fc2)/3 |
5951 reflections | (Δ/σ)max < 0.001 |
627 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
Special details top
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 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O3 | 0.2086 (2) | 0.25126 (6) | 0.31273 (6) | 0.0388 (5) | |
O4 | 0.15474 (18) | 0.16421 (5) | 0.39394 (6) | 0.0310 (4) | |
O5 | 0.12160 (19) | 0.18298 (5) | 0.52203 (6) | 0.0317 (4) | |
N1 | −0.1165 (2) | 0.44433 (7) | 0.60943 (8) | 0.0269 (5) | |
N2 | −0.4164 (2) | 0.48104 (8) | 0.59187 (9) | 0.0317 (5) | |
N3 | −0.2813 (2) | 0.45343 (6) | 0.50171 (7) | 0.0243 (4) | |
N4 | −0.1480 (3) | 0.42782 (7) | 0.41176 (8) | 0.0294 (5) | |
C2 | −0.2703 (3) | 0.45939 (7) | 0.56726 (8) | 0.0244 (5) | |
C4 | −0.1318 (2) | 0.43258 (7) | 0.47728 (8) | 0.0231 (5) | |
C5 | 0.0373 (2) | 0.41617 (7) | 0.51969 (8) | 0.0239 (5) | |
C6 | 0.0351 (3) | 0.42325 (8) | 0.58539 (9) | 0.0269 (5) | |
C7 | 0.2069 (3) | 0.39311 (8) | 0.49325 (10) | 0.0280 (6) | |
C8 | 0.1871 (2) | 0.33190 (8) | 0.46688 (9) | 0.0241 (5) | |
C9 | 0.2058 (2) | 0.32122 (8) | 0.40121 (9) | 0.0262 (5) | |
C10 | 0.1928 (2) | 0.26531 (8) | 0.37706 (8) | 0.0267 (5) | |
C11 | 0.1632 (2) | 0.21970 (7) | 0.41838 (9) | 0.0249 (5) | |
C12 | 0.1480 (2) | 0.23072 (8) | 0.48494 (9) | 0.0250 (5) | |
C13 | 0.1592 (2) | 0.28677 (8) | 0.50898 (9) | 0.0248 (5) | |
C14 | 0.2066 (4) | 0.29777 (11) | 0.26603 (11) | 0.0447 (8) | |
C15 | −0.0336 (3) | 0.14312 (10) | 0.37733 (13) | 0.0415 (7) | |
C16 | 0.1226 (3) | 0.19124 (10) | 0.59154 (10) | 0.0324 (6) | |
O3A | 0.7323 (2) | 0.25401 (6) | 0.27892 (6) | 0.0419 (5) | |
O4A | 0.73218 (18) | 0.17080 (5) | 0.18802 (6) | 0.0320 (4) | |
O5A | 0.6587 (2) | 0.19370 (6) | 0.05887 (6) | 0.0350 (4) | |
N1A | 0.4728 (2) | 0.42514 (7) | −0.07646 (7) | 0.0262 (5) | |
N2A | 0.6395 (3) | 0.46965 (8) | −0.14905 (8) | 0.0328 (5) | |
N3A | 0.7644 (2) | 0.46739 (6) | −0.03793 (7) | 0.0247 (4) | |
N4A | 0.8883 (2) | 0.46221 (8) | 0.07139 (8) | 0.0326 (5) | |
C2A | 0.6277 (2) | 0.45456 (7) | −0.08727 (8) | 0.0237 (5) | |
C4A | 0.7473 (2) | 0.44981 (7) | 0.02405 (8) | 0.0230 (5) | |
C5A | 0.5838 (2) | 0.41962 (7) | 0.03831 (8) | 0.0223 (5) | |
C6A | 0.4510 (3) | 0.40909 (7) | −0.01403 (9) | 0.0248 (5) | |
C7A | 0.5570 (3) | 0.40095 (8) | 0.10692 (9) | 0.0251 (5) | |
C8A | 0.6161 (2) | 0.33949 (7) | 0.12627 (8) | 0.0226 (5) | |
C9A | 0.6548 (3) | 0.32691 (8) | 0.19363 (9) | 0.0281 (6) | |
C10A | 0.6911 (3) | 0.27082 (8) | 0.21422 (8) | 0.0281 (5) | |
C11A | 0.6890 (2) | 0.22668 (8) | 0.16779 (9) | 0.0258 (5) | |
C12A | 0.6538 (2) | 0.23953 (8) | 0.10047 (8) | 0.0240 (5) | |
C13A | 0.6173 (2) | 0.29617 (8) | 0.07973 (8) | 0.0234 (5) | |
C14A | 0.7351 (4) | 0.29752 (12) | 0.32819 (10) | 0.0469 (8) | |
C15A | 0.5799 (4) | 0.14029 (11) | 0.20911 (14) | 0.0456 (8) | |
C16A | 0.6522 (3) | 0.20627 (9) | −0.00964 (9) | 0.0317 (6) | |
S1 | 0.06550 (6) | 0.46246 (2) | 0.25336 (2) | 0.0243 (1) | |
O6 | 0.1140 (2) | 0.52387 (6) | 0.26534 (6) | 0.0347 (4) | |
O7 | 0.0962 (2) | 0.43137 (6) | 0.31571 (7) | 0.0426 (5) | |
O8 | −0.1317 (2) | 0.45910 (7) | 0.22252 (8) | 0.0479 (5) | |
O9 | 0.1836 (2) | 0.43906 (6) | 0.20703 (7) | 0.0447 (5) | |
O1' | 0.2813 (2) | 0.06925 (8) | 0.29492 (8) | 0.0446 (5) | |
O2' | 0.5571 (3) | 0.45244 (8) | 0.29707 (8) | 0.0487 (6) | |
O3' | 0.1171 (2) | 0.15968 (7) | 0.22232 (8) | 0.0468 (5) | |
H1 | −0.114 (3) | 0.4514 (10) | 0.6511 (12) | 0.047 (7)* | |
H2 | 0.147 (3) | 0.2944 (8) | 0.5538 (10) | 0.024 (5)* | |
H6 | 0.021 (3) | 0.2149 (9) | 0.5999 (10) | 0.037 (6)* | |
H10 | 0.142 (3) | 0.4145 (9) | 0.6172 (10) | 0.032 (5)* | |
H11 | 0.242 (3) | 0.2074 (9) | 0.6132 (10) | 0.038 (6)* | |
H12 | 0.312 (3) | 0.3934 (8) | 0.5302 (10) | 0.030 (5)* | |
H14 | 0.236 (3) | 0.4178 (9) | 0.4593 (10) | 0.029 (5)* | |
H15 | 0.225 (3) | 0.3521 (9) | 0.3736 (10) | 0.030 (5)* | |
H21 | −0.252 (4) | 0.4383 (10) | 0.3872 (12) | 0.045 (7)* | |
H24 | −0.025 (3) | 0.1062 (12) | 0.3600 (12) | 0.053 (7)* | |
H26 | 0.108 (3) | 0.1545 (10) | 0.6097 (11) | 0.041 (6)* | |
H30 | −0.052 (3) | 0.4219 (10) | 0.3905 (12) | 0.046 (7)* | |
H32 | −0.096 (4) | 0.1425 (12) | 0.4169 (14) | 0.067 (8)* | |
H33 | −0.101 (3) | 0.1687 (11) | 0.3447 (12) | 0.050 (7)* | |
H34 | 0.087 (4) | 0.3192 (11) | 0.2638 (12) | 0.057 (7)* | |
H35 | 0.317 (4) | 0.3246 (13) | 0.2777 (13) | 0.069 (8)* | |
H39 | 0.219 (4) | 0.2776 (14) | 0.2271 (15) | 0.078 (9)* | |
H40 | −0.502 (3) | 0.4976 (10) | 0.5649 (12) | 0.041 (6)* | |
H41 | −0.405 (3) | 0.4915 (10) | 0.6324 (12) | 0.042 (6)* | |
H3 | 0.623 (3) | 0.4259 (8) | 0.1399 (10) | 0.026 (5)* | |
H4 | 0.424 (3) | 0.4034 (9) | 0.1095 (10) | 0.032 (5)* | |
H5 | 0.654 (3) | 0.1703 (10) | −0.0320 (11) | 0.040 (6)* | |
H7 | 0.336 (3) | 0.3901 (9) | −0.0112 (9) | 0.028 (5)* | |
H8 | 0.551 (3) | 0.4600 (8) | −0.1774 (10) | 0.023 (5)* | |
H13 | 0.651 (3) | 0.3576 (9) | 0.2248 (10) | 0.032 (5)* | |
H17 | 0.758 (3) | 0.2311 (10) | −0.0165 (11) | 0.046 (6)* | |
H18 | 0.627 (3) | 0.1044 (12) | 0.2217 (12) | 0.052 (7)* | |
H19 | 0.535 (3) | 0.2244 (9) | −0.0269 (10) | 0.034 (5)* | |
H20 | 0.542 (4) | 0.1595 (13) | 0.2462 (14) | 0.071 (9)* | |
H22 | 0.989 (3) | 0.4805 (10) | 0.0587 (11) | 0.042 (6)* | |
H23 | 0.726 (4) | 0.4948 (11) | −0.1610 (12) | 0.056 (7)* | |
H27 | 0.885 (3) | 0.4524 (10) | 0.1137 (12) | 0.041 (6)* | |
H28 | 0.617 (4) | 0.3126 (11) | 0.3286 (12) | 0.054 (7)* | |
H29 | 0.776 (3) | 0.2781 (10) | 0.3695 (13) | 0.051 (7)* | |
H31 | 0.590 (3) | 0.3050 (8) | 0.0338 (10) | 0.027 (5)* | |
H36 | 0.474 (4) | 0.1388 (12) | 0.1740 (15) | 0.073 (9)* | |
H37 | 0.391 (3) | 0.4184 (10) | −0.1098 (12) | 0.043 (6)* | |
H38 | 0.830 (4) | 0.3295 (13) | 0.3197 (14) | 0.072 (9)* | |
H1' | 0.230 (3) | 0.1004 (9) | 0.2760 (9) | 0.016 (4)* | |
H2' | 0.207 (4) | 0.0376 (14) | 0.2864 (14) | 0.075 (9)* | |
H3' | 0.467 (4) | 0.4452 (11) | 0.2783 (13) | 0.046 (8)* | |
H4' | 0.639 (4) | 0.4542 (12) | 0.2687 (15) | 0.070 (9)* | |
H5' | 0.143 (5) | 0.1885 (16) | 0.2604 (18) | 0.103 (12)* | |
H6' | −0.030 (7) | 0.158 (2) | 0.217 (2) | 0.169 (19)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.0575 (9) | 0.0392 (8) | 0.0199 (7) | 0.0030 (7) | 0.0063 (6) | −0.0029 (6) |
O4 | 0.0333 (7) | 0.0257 (7) | 0.0320 (7) | 0.0040 (5) | −0.0015 (5) | −0.0060 (5) |
O5 | 0.0431 (8) | 0.0262 (7) | 0.0266 (7) | 0.0013 (6) | 0.0078 (6) | 0.0039 (5) |
N1 | 0.0348 (9) | 0.0278 (8) | 0.0172 (8) | 0.0011 (7) | 0.0009 (6) | −0.0027 (6) |
N2 | 0.0359 (9) | 0.0393 (10) | 0.0201 (8) | 0.0059 (8) | 0.0051 (7) | −0.0042 (7) |
N3 | 0.0289 (8) | 0.0240 (8) | 0.0195 (7) | 0.0007 (6) | 0.0021 (6) | −0.0018 (6) |
N4 | 0.0316 (9) | 0.0370 (9) | 0.0196 (8) | 0.0052 (7) | 0.0036 (7) | −0.0017 (7) |
C2 | 0.0319 (9) | 0.0201 (8) | 0.0210 (8) | −0.0030 (7) | 0.0032 (7) | −0.0007 (7) |
C4 | 0.0301 (9) | 0.0172 (8) | 0.0218 (9) | −0.0030 (7) | 0.0031 (7) | −0.0009 (7) |
C5 | 0.0276 (9) | 0.0177 (8) | 0.0258 (9) | −0.0024 (7) | 0.0017 (7) | −0.0019 (7) |
C6 | 0.0314 (10) | 0.0220 (9) | 0.0253 (9) | 0.0004 (7) | −0.0028 (8) | −0.0005 (7) |
C7 | 0.0261 (9) | 0.0264 (10) | 0.0307 (10) | −0.0025 (7) | 0.0020 (8) | −0.0017 (8) |
C8 | 0.0187 (8) | 0.0271 (9) | 0.0257 (9) | 0.0026 (7) | 0.0003 (7) | −0.0009 (7) |
C9 | 0.0257 (9) | 0.0275 (10) | 0.0245 (9) | 0.0012 (7) | 0.0012 (7) | 0.0051 (8) |
C10 | 0.0262 (9) | 0.0349 (10) | 0.0182 (8) | 0.0039 (8) | 0.0004 (7) | −0.0003 (7) |
C11 | 0.0223 (8) | 0.0242 (9) | 0.0270 (9) | 0.0043 (7) | −0.0003 (7) | −0.0043 (7) |
C12 | 0.0226 (9) | 0.0274 (9) | 0.0248 (9) | 0.0034 (7) | 0.0031 (7) | 0.0036 (7) |
C13 | 0.0236 (9) | 0.0289 (10) | 0.0221 (9) | 0.0032 (7) | 0.0041 (7) | −0.0024 (7) |
C14 | 0.0615 (16) | 0.0503 (14) | 0.0232 (11) | −0.0020 (12) | 0.0089 (10) | 0.0047 (10) |
C15 | 0.0429 (12) | 0.0337 (12) | 0.0478 (13) | −0.0099 (10) | 0.0061 (11) | −0.0068 (11) |
C16 | 0.0335 (11) | 0.0377 (11) | 0.0276 (10) | 0.0047 (9) | 0.0098 (8) | 0.0055 (9) |
O3A | 0.0645 (10) | 0.0408 (8) | 0.0181 (7) | 0.0053 (7) | −0.0012 (6) | 0.0052 (6) |
O4A | 0.0336 (7) | 0.0297 (7) | 0.0330 (7) | 0.0064 (6) | 0.0058 (6) | 0.0093 (6) |
O5A | 0.0539 (9) | 0.0268 (7) | 0.0240 (7) | 0.0087 (6) | 0.0051 (6) | −0.0016 (5) |
N1A | 0.0273 (8) | 0.0286 (8) | 0.0208 (8) | −0.0032 (6) | −0.0026 (6) | 0.0009 (6) |
N2A | 0.0366 (10) | 0.0387 (10) | 0.0226 (8) | −0.0048 (8) | 0.0029 (7) | 0.0046 (7) |
N3A | 0.0246 (7) | 0.0256 (8) | 0.0239 (8) | −0.0017 (6) | 0.0036 (6) | −0.0006 (6) |
N4A | 0.0297 (9) | 0.0412 (10) | 0.0253 (9) | −0.0093 (7) | −0.0008 (7) | 0.0009 (7) |
C2A | 0.0279 (9) | 0.0200 (8) | 0.0237 (9) | 0.0024 (7) | 0.0051 (7) | 0.0016 (7) |
C4A | 0.0252 (9) | 0.0193 (8) | 0.0243 (9) | 0.0014 (7) | 0.0027 (7) | −0.0012 (7) |
C5A | 0.0259 (9) | 0.0179 (8) | 0.0228 (9) | −0.0003 (7) | 0.0031 (7) | 0.0001 (7) |
C6A | 0.0272 (9) | 0.0215 (9) | 0.0257 (9) | −0.0027 (7) | 0.0035 (7) | 0.0016 (7) |
C7A | 0.0295 (10) | 0.0240 (9) | 0.0221 (9) | −0.0025 (8) | 0.0045 (7) | −0.0010 (7) |
C8A | 0.0190 (8) | 0.0266 (9) | 0.0224 (9) | −0.0019 (7) | 0.0039 (6) | 0.0023 (7) |
C9A | 0.0330 (10) | 0.0300 (10) | 0.0212 (9) | −0.0019 (8) | 0.0034 (7) | −0.0030 (8) |
C10A | 0.0295 (9) | 0.0358 (10) | 0.0183 (9) | 0.0002 (8) | 0.0012 (7) | 0.0043 (7) |
C11A | 0.0232 (9) | 0.0275 (9) | 0.0265 (9) | 0.0024 (7) | 0.0028 (7) | 0.0058 (7) |
C12A | 0.0218 (8) | 0.0274 (9) | 0.0227 (9) | 0.0008 (7) | 0.0034 (7) | −0.0008 (7) |
C13A | 0.0230 (9) | 0.0279 (9) | 0.0190 (9) | −0.0003 (7) | 0.0022 (7) | 0.0025 (7) |
C14A | 0.0536 (14) | 0.0671 (16) | 0.0175 (10) | 0.0191 (13) | −0.0028 (10) | −0.0026 (10) |
C15A | 0.0494 (14) | 0.0316 (12) | 0.0571 (15) | −0.0006 (10) | 0.0121 (12) | 0.0112 (11) |
C16A | 0.0352 (11) | 0.0367 (11) | 0.0226 (9) | 0.0064 (9) | 0.0028 (8) | −0.0045 (8) |
S1 | 0.0301 (2) | 0.0267 (2) | 0.0162 (2) | −0.0033 (2) | 0.0037 (2) | 0.0009 (2) |
O6 | 0.0503 (8) | 0.0314 (7) | 0.0229 (7) | −0.0094 (6) | 0.0068 (6) | −0.0036 (5) |
O7 | 0.0601 (10) | 0.0434 (9) | 0.0257 (7) | 0.0091 (7) | 0.0106 (7) | 0.0121 (6) |
O8 | 0.0363 (8) | 0.0499 (9) | 0.0532 (9) | −0.0071 (7) | −0.0074 (7) | −0.0013 (7) |
O9 | 0.0654 (10) | 0.0383 (8) | 0.0364 (8) | −0.0052 (7) | 0.0275 (7) | −0.0052 (6) |
O1' | 0.0429 (9) | 0.0411 (9) | 0.0443 (9) | −0.0021 (8) | −0.0111 (7) | −0.0043 (7) |
O2' | 0.0396 (9) | 0.0735 (12) | 0.0321 (8) | 0.0057 (9) | 0.0026 (8) | −0.0048 (8) |
O3' | 0.0428 (9) | 0.0461 (9) | 0.0493 (9) | 0.0063 (7) | 0.0000 (7) | −0.0085 (7) |
Geometric parameters (Å, º) top
S1—O9 | 1.4684 (15) | C5—C6 | 1.351 (2) |
S1—O6 | 1.4812 (15) | C7—C8 | 1.520 (3) |
S1—O7 | 1.4494 (15) | C8—C9 | 1.387 (3) |
S1—O8 | 1.4716 (16) | C8—C13 | 1.389 (3) |
O3—C14 | 1.439 (3) | C9—C10 | 1.388 (3) |
O3—C10 | 1.372 (2) | C10—C11 | 1.390 (2) |
O4—C11 | 1.381 (2) | C11—C12 | 1.400 (3) |
O4—C15 | 1.439 (3) | C12—C13 | 1.390 (3) |
O5—C12 | 1.372 (2) | C6—H10 | 0.95 (2) |
O5—C16 | 1.428 (2) | C7—H12 | 0.99 (2) |
O3A—C14A | 1.423 (3) | C7—H14 | 0.95 (2) |
O3A—C10A | 1.364 (2) | C9—H15 | 0.93 (2) |
O4A—C15A | 1.428 (3) | C13—H2 | 0.95 (2) |
O4A—C11A | 1.384 (2) | C14—H35 | 1.01 (3) |
O5A—C16A | 1.420 (2) | C14—H34 | 0.99 (3) |
O5A—C12A | 1.365 (2) | C14—H39 | 0.94 (3) |
O1'—H2' | 0.91 (3) | C15—H33 | 0.97 (2) |
O1'—H1' | 0.88 (2) | C15—H32 | 0.98 (3) |
O2'—H3' | 0.72 (3) | C15—H24 | 0.93 (3) |
O2'—H4' | 0.89 (3) | C16—H26 | 0.94 (2) |
N1—C6 | 1.357 (3) | C16—H6 | 0.95 (2) |
N1—C2 | 1.346 (2) | C16—H11 | 0.98 (2) |
N2—C2 | 1.334 (3) | C4A—C5A | 1.441 (2) |
N3—C2 | 1.333 (2) | C5A—C6A | 1.346 (3) |
N3—C4 | 1.346 (2) | C5A—C7A | 1.504 (2) |
N4—C4 | 1.327 (2) | C7A—C8A | 1.526 (2) |
N1—H1 | 0.86 (2) | C8A—C9A | 1.390 (2) |
N2—H40 | 0.86 (2) | C8A—C13A | 1.384 (2) |
N2—H41 | 0.85 (2) | C9A—C10A | 1.383 (3) |
O3'—H6' | 1.05 (5) | C10A—C11A | 1.394 (3) |
O3'—H5' | 1.02 (4) | C11A—C12A | 1.390 (2) |
N4—H30 | 0.88 (2) | C12A—C13A | 1.396 (3) |
N4—H21 | 0.87 (3) | C6A—H7 | 0.95 (2) |
N1A—C2A | 1.358 (2) | C7A—H4 | 0.97 (2) |
N1A—C6A | 1.357 (2) | C7A—H3 | 0.96 (2) |
N2A—C2A | 1.322 (2) | C9A—H13 | 0.96 (2) |
N3A—C4A | 1.350 (2) | C13A—H31 | 0.95 (2) |
N3A—C2A | 1.334 (2) | C14A—H28 | 0.92 (3) |
N4A—C4A | 1.326 (2) | C14A—H38 | 1.04 (3) |
N1A—H37 | 0.85 (2) | C14A—H29 | 0.96 (3) |
N2A—H23 | 0.92 (3) | C15A—H36 | 0.97 (3) |
N2A—H8 | 0.83 (2) | C15A—H20 | 0.95 (3) |
N4A—H22 | 0.91 (2) | C15A—H18 | 0.92 (3) |
N4A—H27 | 0.90 (2) | C16A—H5 | 0.95 (2) |
C4—C5 | 1.439 (2) | C16A—H17 | 0.98 (2) |
C5—C7 | 1.509 (3) | C16A—H19 | 0.96 (2) |
| | | |
S1···N1i | 3.5122 (17) | C13···H6 | 2.79 (2) |
S1···H2'ii | 2.67 (3) | C13A···H11viii | 2.90 (2) |
S1···H1i | 2.78 (2) | C13A···H6xii | 2.90 (2) |
S1···H23iii | 2.77 (3) | C13A···H17 | 2.79 (2) |
S1···H3' | 2.90 (3) | C13A···H19 | 2.73 (2) |
S1···H4'iv | 3.15 (3) | C14···H15 | 2.52 (2) |
S1···H27iv | 2.96 (2) | C14···H5' | 2.58 (4) |
S1···H30 | 3.18 (2) | C14···H28 | 3.07 (3) |
O1'···O6v | 3.121 (2) | C14A···H5vi | 3.08 (2) |
O1'···O8v | 2.781 (2) | C14A···H34vii | 3.07 (3) |
O1'···N1Avi | 2.778 (2) | C14A···H13 | 2.52 (2) |
O1'···O3' | 2.737 (2) | C15···H5' | 3.05 (4) |
O1'···O4 | 3.214 (2) | C15A···H6'vii | 2.83 (5) |
O1'···C15A | 3.401 (3) | C16···H4vi | 3.08 (2) |
O1'···C2Avi | 3.247 (2) | C16···H2 | 2.532 (19) |
O1'···N2Avi | 2.818 (3) | C16···H39vi | 2.84 (3) |
O2'···N2i | 3.038 (3) | C16A···H31 | 2.524 (19) |
O2'···O9 | 3.045 (2) | C16A···H29viii | 2.77 (3) |
O2'···N4vii | 2.974 (3) | H1···H41 | 2.28 (3) |
O2'···O8vii | 2.900 (3) | H1···O6i | 1.80 (2) |
O3···O4 | 2.6786 (18) | H1···S1i | 2.78 (2) |
O3···O3' | 2.828 (2) | H1···O7i | 2.81 (2) |
O3'···C14 | 3.368 (3) | H1'···H37vi | 2.48 (3) |
O3'···O4Aiv | 2.778 (2) | H1'···H5' | 2.15 (4) |
O3'···O1' | 2.737 (2) | H1'···O3' | 1.87 (2) |
O3'···C6viii | 3.370 (2) | H1'···H6' | 2.47 (5) |
O3'···O3 | 2.828 (2) | H2···H6 | 2.32 (3) |
O3A···C15A | 3.123 (3) | H2···C5 | 2.993 (19) |
O3A···O4A | 2.6776 (18) | H2···H11 | 2.40 (3) |
O4···O1' | 3.214 (2) | H2···C16 | 2.532 (19) |
O4···N1Avi | 3.090 (2) | H2'···H37vi | 2.54 (4) |
O4···O5 | 2.6915 (18) | H2'···H8vi | 2.49 (4) |
O4···C6Avi | 3.131 (2) | H2'···O8v | 1.90 (3) |
O4···O3 | 2.6786 (18) | H2'···O6v | 2.42 (3) |
O4A···O3A | 2.6776 (18) | H2'···H4'xiv | 2.57 (4) |
O4A···O3'vii | 2.778 (2) | H2'···S1v | 2.67 (3) |
O4A···O5A | 2.6591 (18) | H3···N4A | 2.67 (2) |
O5···C15 | 3.134 (3) | H3···H27 | 2.13 (3) |
O5···O4 | 2.6915 (18) | H3···O8vii | 2.38 (2) |
O5···C6Avi | 3.363 (2) | H3···H13 | 2.33 (3) |
O5A···O4A | 2.6591 (18) | H3'···O9 | 2.33 (3) |
O6···N1i | 2.654 (2) | H3'···H41i | 2.43 (4) |
O6···N2Aiii | 3.174 (2) | H3'···S1 | 2.90 (3) |
O6···O1'ii | 3.121 (2) | H3'···O7 | 2.91 (3) |
O7···N4 | 2.826 (2) | H4···H7 | 2.47 (3) |
O7···C14 | 3.398 (3) | H4···C16viii | 3.08 (2) |
O7···C9 | 3.131 (2) | H4'···H2'ix | 2.57 (4) |
O7···N1i | 3.260 (2) | H4'···S1vii | 3.15 (3) |
O8···C7Aiv | 3.295 (3) | H4'···H13 | 2.42 (4) |
O8···O2'iv | 2.900 (3) | H4'···O8vii | 2.03 (3) |
O8···O1'ii | 2.781 (2) | H4'···H21vii | 2.45 (4) |
O8···N4Aiv | 3.105 (2) | H5···C14Aviii | 3.08 (2) |
O9···O2' | 3.045 (2) | H5···C4xii | 2.84 (2) |
O9···N2Aiii | 2.826 (2) | H5'···O3 | 1.83 (4) |
O1'···H8vi | 2.06 (2) | H5'···H39 | 2.27 (5) |
O1'···H24 | 2.88 (2) | H5'···C14 | 2.58 (4) |
O1'···H37vi | 2.00 (2) | H5'···C15 | 3.05 (4) |
O2'···H21vii | 2.15 (3) | H5'···C10 | 2.95 (4) |
O2'···H41i | 2.33 (2) | H5'···O4 | 2.77 (4) |
O2'···H13 | 2.79 (2) | H5'···H1' | 2.15 (4) |
O3···H5' | 1.83 (4) | H6···C12Axiii | 2.86 (2) |
O3'···H39 | 2.84 (3) | H6···H2 | 2.32 (3) |
O3'···H1' | 1.87 (2) | H6···C13Axiii | 2.90 (2) |
O3'···H10viii | 2.78 (2) | H6···C13 | 2.79 (2) |
O3A···H33vii | 2.59 (2) | H6'···C11Aiv | 2.66 (5) |
O3A···H20 | 2.62 (3) | H6'···O4Aiv | 1.76 (5) |
O4···H5' | 2.77 (4) | H6'···H1' | 2.47 (5) |
O4···H7vi | 2.51 (2) | H6'···C15Aiv | 2.83 (5) |
O4···H37vi | 2.58 (2) | H7···O5viii | 2.46 (2) |
O4A···H6'vii | 1.76 (5) | H7···H4 | 2.47 (3) |
O5···H32 | 2.63 (3) | H7···O4viii | 2.51 (2) |
O5···H7vi | 2.46 (2) | H7···C11viii | 3.10 (2) |
O6···H2'ii | 2.42 (3) | H8···H37 | 2.16 (3) |
O6···H1i | 1.80 (2) | H8···O1'viii | 2.06 (2) |
O6···H41i | 2.75 (2) | H8···H2'viii | 2.49 (4) |
O6···H23iii | 2.60 (3) | H10···O3'vi | 2.78 (2) |
O6···H18ix | 2.63 (3) | H10···H12 | 2.35 (3) |
O7···H15 | 2.31 (2) | H11···H2 | 2.40 (3) |
O7···H34 | 2.81 (3) | H11···C8Avi | 2.89 (2) |
O7···H1i | 2.81 (2) | H11···C13Avi | 2.90 (2) |
O7···H3' | 2.91 (3) | H11···H39vi | 2.38 (4) |
O7···H30 | 2.00 (2) | H11···C13 | 2.81 (2) |
O8···H3iv | 2.38 (2) | H12···H10 | 2.35 (3) |
O8···H4'iv | 2.03 (3) | H13···H4' | 2.42 (4) |
O8···H2'ii | 1.90 (3) | H13···H28 | 2.40 (3) |
O8···H27iv | 2.24 (2) | H13···H3 | 2.33 (3) |
O8···H13iv | 2.84 (2) | H13···O2' | 2.79 (2) |
O9···H3' | 2.33 (3) | H13···O8vii | 2.84 (2) |
O9···H27iv | 2.67 (2) | H13···H38 | 2.26 (4) |
O9···H23iii | 1.96 (3) | H13···C14A | 2.52 (2) |
N1···O6i | 2.654 (2) | H14···H15 | 2.31 (3) |
N1···S1i | 3.5122 (17) | H14···H30 | 2.33 (3) |
N1···O7i | 3.260 (2) | H14···C2i | 2.92 (2) |
N1A···O1'viii | 2.778 (2) | H14···N4 | 2.81 (2) |
N1A···O4viii | 3.090 (2) | H15···C14 | 2.52 (2) |
N2···O2'i | 3.038 (3) | H15···H14 | 2.31 (3) |
N2···N3x | 3.080 (2) | H15···O7 | 2.31 (2) |
N2A···O1'viii | 2.818 (3) | H15···H35 | 2.25 (3) |
N2A···O9iii | 2.826 (2) | H15···H34 | 2.43 (3) |
N2A···O6iii | 3.174 (2) | H17···H31 | 2.42 (3) |
N3···N2x | 3.080 (2) | H17···C12xii | 2.95 (2) |
N3A···N4Axi | 3.155 (2) | H17···C13A | 2.79 (2) |
N4···O2'iv | 2.974 (3) | H17···H29viii | 2.36 (3) |
N4···O7 | 2.826 (2) | H17···C13xii | 2.90 (2) |
N4···C8 | 3.360 (3) | H18···O6xiv | 2.63 (3) |
N4A···N3Axi | 3.155 (2) | H19···C13A | 2.73 (2) |
N4A···O8vii | 3.105 (2) | H19···C12viii | 3.03 (2) |
N3···H40x | 2.23 (2) | H19···C11viii | 3.04 (2) |
N3A···H22xi | 2.25 (2) | H19···H31 | 2.25 (3) |
N3A···H32xii | 2.94 (3) | H19···C8viii | 2.82 (2) |
N4···H14 | 2.81 (2) | H19···C9viii | 2.81 (2) |
N4···H38iv | 2.95 (3) | H19···C10viii | 2.93 (2) |
N4A···H3 | 2.67 (2) | H19···C13viii | 2.93 (2) |
C2A···O1'viii | 3.247 (2) | H20···O3A | 2.62 (3) |
C2A···C15xii | 3.492 (3) | H20···C10A | 2.91 (3) |
C2A···C5Aiii | 3.513 (2) | H21···H4'iv | 2.45 (4) |
C4···C5i | 3.580 (2) | H21···O2'iv | 2.15 (3) |
C4A···C6Aiii | 3.573 (2) | H22···H22xi | 2.58 (3) |
C5···C4i | 3.580 (2) | H22···N3Axi | 2.25 (2) |
C5A···C2Aiii | 3.513 (2) | H23···O9iii | 1.96 (3) |
C6···O3'vi | 3.370 (2) | H23···O6iii | 2.60 (3) |
C6A···C13A | 3.361 (3) | H23···S1iii | 2.77 (3) |
C6A···O5viii | 3.363 (2) | H24···O1' | 2.88 (2) |
C6A···O4viii | 3.131 (2) | H27···O8vii | 2.24 (2) |
C6A···C4Aiii | 3.573 (2) | H27···O9vii | 2.67 (2) |
C7A···O8vii | 3.295 (3) | H27···S1vii | 2.96 (2) |
C8···N4 | 3.360 (3) | H27···H3 | 2.13 (3) |
C8···C16Avi | 3.441 (3) | H27···C7A | 2.64 (2) |
C9···C16Avi | 3.517 (3) | H28···C9A | 2.82 (2) |
C9···O7 | 3.131 (2) | H28···H35 | 2.28 (4) |
C9···C14Aiv | 3.547 (3) | H28···C14 | 3.07 (3) |
C10···C14Aiv | 3.393 (3) | H28···H13 | 2.40 (3) |
C13A···C6A | 3.361 (3) | H29···C10vii | 3.01 (2) |
C14···O7 | 3.398 (3) | H29···C16Avi | 2.77 (3) |
C14···O3' | 3.368 (3) | H29···H17vi | 2.36 (3) |
C14···C16viii | 3.525 (3) | H30···C8 | 3.00 (2) |
C14A···C9vii | 3.547 (3) | H30···O7 | 2.00 (2) |
C14A···C10vii | 3.393 (3) | H30···C7 | 2.68 (2) |
C14A···C16Avi | 3.446 (3) | H30···H14 | 2.33 (3) |
C15···C2Axiii | 3.492 (3) | H30···S1 | 3.18 (2) |
C15···O5 | 3.134 (3) | H30···C9 | 2.98 (2) |
C15A···O1' | 3.401 (3) | H31···C5A | 2.666 (19) |
C15A···O3A | 3.123 (3) | H31···C6A | 2.742 (19) |
C16···C14vi | 3.525 (3) | H31···C16A | 2.524 (19) |
C16A···C14Aviii | 3.446 (3) | H31···H17 | 2.42 (3) |
C16A···C8viii | 3.441 (3) | H31···H19 | 2.25 (3) |
C16A···C9viii | 3.517 (3) | H32···O5 | 2.63 (3) |
C2···H14i | 2.92 (2) | H32···C12 | 2.92 (3) |
C2A···H32xii | 3.01 (3) | H32···C2Axiii | 3.01 (3) |
C4···H5xiii | 2.84 (2) | H32···N3Axiii | 2.94 (3) |
C5···H2 | 2.993 (19) | H33···O3Aiv | 2.59 (2) |
C5A···H31 | 2.666 (19) | H33···C10 | 3.09 (2) |
C6A···H31 | 2.742 (19) | H34···O7 | 2.81 (3) |
C7···H30 | 2.68 (2) | H34···C9 | 2.80 (2) |
C7A···H27 | 2.64 (2) | H34···C14Aiv | 3.07 (3) |
C8···H19vi | 2.82 (2) | H34···H15 | 2.43 (3) |
C8···H30 | 3.00 (2) | H34···H38iv | 2.33 (4) |
C8A···H11viii | 2.89 (2) | H35···H28 | 2.28 (4) |
C9···H38iv | 2.97 (3) | H35···H15 | 2.25 (3) |
C9···H19vi | 2.81 (2) | H35···C9 | 2.75 (3) |
C9···H34 | 2.80 (2) | H37···H1'viii | 2.48 (3) |
C9···H35 | 2.75 (3) | H37···H2'viii | 2.54 (4) |
C9···H30 | 2.98 (2) | H37···O4viii | 2.58 (2) |
C9A···H38 | 2.69 (3) | H37···H8 | 2.16 (3) |
C9A···H28 | 2.82 (2) | H37···O1'viii | 2.00 (2) |
C10···H33 | 3.09 (2) | H38···C9A | 2.69 (3) |
C10···H29iv | 3.01 (2) | H38···N4vii | 2.95 (3) |
C10···H38iv | 3.09 (3) | H38···H13 | 2.26 (4) |
C10···H19vi | 2.93 (2) | H38···H34vii | 2.33 (4) |
C10···H5' | 2.95 (4) | H38···C9vii | 2.97 (3) |
C10A···H20 | 2.91 (3) | H38···C10vii | 3.09 (3) |
C11···H7vi | 3.10 (2) | H39···O3' | 2.84 (3) |
C11···H19vi | 3.04 (2) | H39···H5' | 2.27 (5) |
C11A···H6'vii | 2.66 (5) | H39···C16viii | 2.84 (3) |
C12···H17xiii | 2.95 (2) | H39···H11viii | 2.38 (4) |
C12···H32 | 2.92 (3) | H40···N3x | 2.23 (2) |
C12···H19vi | 3.03 (2) | H41···O2'i | 2.33 (2) |
C12A···H6xii | 2.86 (2) | H41···O6i | 2.75 (2) |
C13···H17xiii | 2.90 (2) | H41···H3'i | 2.43 (4) |
C13···H19vi | 2.93 (2) | H41···H1 | 2.28 (3) |
C13···H11 | 2.81 (2) | | |
| | | |
O6—S1—O7 | 109.54 (8) | O3—C14—H34 | 109.3 (15) |
O6—S1—O8 | 108.17 (9) | O3—C14—H39 | 101 (2) |
O6—S1—O9 | 108.47 (8) | H34—C14—H35 | 111 (2) |
O7—S1—O8 | 111.07 (9) | H34—C14—H39 | 114 (2) |
O7—S1—O9 | 110.55 (8) | H35—C14—H39 | 110 (2) |
O8—S1—O9 | 108.97 (9) | O4—C15—H32 | 110.3 (17) |
C10—O3—C14 | 117.31 (16) | O4—C15—H24 | 106.7 (14) |
C11—O4—C15 | 113.10 (14) | H32—C15—H33 | 109 (2) |
C12—O5—C16 | 117.19 (15) | O4—C15—H33 | 108.3 (14) |
C10A—O3A—C14A | 117.13 (16) | H24—C15—H32 | 111 (2) |
C11A—O4A—C15A | 113.94 (15) | H24—C15—H33 | 111 (2) |
C12A—O5A—C16A | 116.72 (15) | H6—C16—H26 | 108.5 (19) |
H1'—O1'—H2' | 113 (2) | O5—C16—H11 | 111.7 (12) |
H3'—O2'—H4' | 108 (3) | O5—C16—H26 | 106.4 (14) |
C2—N1—C6 | 119.88 (16) | H6—C16—H11 | 110.3 (18) |
C2—N3—C4 | 118.48 (16) | O5—C16—H6 | 111.4 (12) |
C6—N1—H1 | 121.7 (15) | H11—C16—H26 | 108.2 (18) |
C2—N1—H1 | 118.2 (15) | N2A—C2A—N3A | 120.83 (16) |
C2—N2—H40 | 117.8 (16) | N1A—C2A—N3A | 121.77 (15) |
H40—N2—H41 | 117 (2) | N1A—C2A—N2A | 117.40 (16) |
C2—N2—H41 | 120.3 (15) | N4A—C4A—C5A | 121.58 (15) |
H5'—O3'—H6' | 100 (3) | N3A—C4A—C5A | 121.89 (14) |
H21—N4—H30 | 116 (2) | N3A—C4A—N4A | 116.52 (14) |
C4—N4—H21 | 119.5 (17) | C4A—C5A—C7A | 123.47 (15) |
C4—N4—H30 | 123.3 (16) | C6A—C5A—C7A | 120.54 (16) |
C2A—N1A—C6A | 120.30 (15) | C4A—C5A—C6A | 115.99 (15) |
C2A—N3A—C4A | 118.43 (14) | N1A—C6A—C5A | 121.56 (18) |
C2A—N1A—H37 | 117.2 (16) | C5A—C7A—C8A | 116.13 (15) |
C6A—N1A—H37 | 122.4 (16) | C7A—C8A—C13A | 122.29 (15) |
C2A—N2A—H23 | 124.5 (16) | C9A—C8A—C13A | 120.16 (16) |
C2A—N2A—H8 | 116.1 (15) | C7A—C8A—C9A | 117.34 (15) |
H8—N2A—H23 | 118 (2) | C8A—C9A—C10A | 119.93 (16) |
H22—N4A—H27 | 122 (2) | O3A—C10A—C11A | 115.06 (16) |
C4A—N4A—H27 | 121.1 (14) | O3A—C10A—C9A | 124.56 (16) |
C4A—N4A—H22 | 117.0 (14) | C9A—C10A—C11A | 120.38 (16) |
N2—C2—N3 | 118.93 (18) | C10A—C11A—C12A | 119.57 (17) |
N1—C2—N3 | 122.17 (18) | O4A—C11A—C12A | 119.70 (16) |
N1—C2—N2 | 118.90 (16) | O4A—C11A—C10A | 120.62 (16) |
N3—C4—C5 | 122.04 (15) | O5A—C12A—C11A | 115.29 (16) |
N3—C4—N4 | 116.55 (16) | O5A—C12A—C13A | 124.71 (15) |
N4—C4—C5 | 121.42 (16) | C11A—C12A—C13A | 120.00 (16) |
C6—C5—C7 | 121.82 (16) | C8A—C13A—C12A | 119.94 (15) |
C4—C5—C7 | 122.84 (15) | N1A—C6A—H7 | 114.2 (11) |
C4—C5—C6 | 115.34 (15) | C5A—C6A—H7 | 124.3 (11) |
N1—C6—C5 | 122.09 (18) | C5A—C7A—H3 | 110.9 (12) |
C5—C7—C8 | 114.83 (16) | C5A—C7A—H4 | 107.4 (12) |
C7—C8—C9 | 119.40 (16) | C8A—C7A—H3 | 107.1 (12) |
C9—C8—C13 | 120.31 (17) | H3—C7A—H4 | 108.6 (18) |
C7—C8—C13 | 120.23 (16) | C8A—C7A—H4 | 106.4 (12) |
C8—C9—C10 | 119.89 (17) | C8A—C9A—H13 | 118.4 (12) |
O3—C10—C11 | 116.06 (16) | C10A—C9A—H13 | 121.6 (12) |
O3—C10—C9 | 123.42 (16) | C12A—C13A—H31 | 120.3 (11) |
C9—C10—C11 | 120.52 (16) | C8A—C13A—H31 | 119.8 (11) |
O4—C11—C12 | 120.96 (15) | O3A—C14A—H38 | 109.3 (16) |
C10—C11—C12 | 119.24 (16) | O3A—C14A—H28 | 111.1 (16) |
O4—C11—C10 | 119.77 (15) | O3A—C14A—H29 | 104.7 (14) |
C11—C12—C13 | 120.25 (16) | H28—C14A—H38 | 111 (2) |
O5—C12—C13 | 124.72 (16) | H29—C14A—H38 | 111 (2) |
O5—C12—C11 | 115.02 (15) | H28—C14A—H29 | 109 (2) |
C8—C13—C12 | 119.77 (17) | O4A—C15A—H18 | 105.3 (14) |
N1—C6—H10 | 116.6 (13) | O4A—C15A—H36 | 110.8 (18) |
C5—C6—H10 | 121.3 (13) | H18—C15A—H20 | 110 (2) |
H12—C7—H14 | 108.9 (17) | O4A—C15A—H20 | 109.4 (18) |
C8—C7—H12 | 107.3 (11) | H20—C15A—H36 | 108 (3) |
C5—C7—H14 | 109.1 (13) | H18—C15A—H36 | 113 (2) |
C8—C7—H14 | 109.2 (13) | O5A—C16A—H17 | 110.4 (13) |
C5—C7—H12 | 107.4 (12) | O5A—C16A—H19 | 110.3 (12) |
C10—C9—H15 | 120.9 (13) | H5—C16A—H19 | 106.4 (18) |
C8—C9—H15 | 119.2 (13) | H17—C16A—H19 | 110.5 (18) |
C8—C13—H2 | 119.8 (11) | H5—C16A—H17 | 112.3 (19) |
C12—C13—H2 | 120.4 (11) | O5A—C16A—H5 | 106.8 (14) |
O3—C14—H35 | 112.2 (16) | | |
| | | |
C14—O3—C10—C9 | −10.8 (2) | C13—C8—C9—C10 | 1.3 (2) |
C14—O3—C10—C11 | 169.46 (17) | C8—C9—C10—O3 | 179.60 (15) |
C15—O4—C11—C10 | −100.71 (18) | C8—C9—C10—C11 | −0.7 (2) |
C15—O4—C11—C12 | 81.2 (2) | C9—C10—C11—C12 | −0.5 (2) |
C16—O5—C12—C11 | 174.34 (15) | C9—C10—C11—O4 | −178.57 (14) |
C16—O5—C12—C13 | −5.9 (2) | O3—C10—C11—C12 | 179.22 (14) |
C14A—O3A—C10A—C11A | −179.66 (19) | O3—C10—C11—O4 | 1.1 (2) |
C14A—O3A—C10A—C9A | 0.9 (3) | O4—C11—C12—C13 | 179.17 (14) |
C15A—O4A—C11A—C12A | −102.13 (19) | C10—C11—C12—O5 | −179.11 (14) |
C15A—O4A—C11A—C10A | 81.6 (2) | O4—C11—C12—O5 | −1.0 (2) |
C16A—O5A—C12A—C11A | −170.57 (15) | C10—C11—C12—C13 | 1.1 (2) |
C16A—O5A—C12A—C13A | 9.3 (2) | O5—C12—C13—C8 | 179.71 (15) |
C6—N1—C2—N3 | 1.2 (3) | C11—C12—C13—C8 | −0.5 (2) |
C6—N1—C2—N2 | −178.73 (17) | N4A—C4A—C5A—C6A | −179.40 (17) |
C2—N1—C6—C5 | −0.6 (3) | N3A—C4A—C5A—C7A | −178.07 (16) |
C2—N3—C4—C5 | 0.6 (2) | N3A—C4A—C5A—C6A | 1.2 (2) |
C4—N3—C2—N2 | 178.73 (16) | N4A—C4A—C5A—C7A | 1.3 (3) |
C2—N3—C4—N4 | −179.41 (16) | C7A—C5A—C6A—N1A | −179.47 (16) |
C4—N3—C2—N1 | −1.2 (2) | C4A—C5A—C6A—N1A | 1.2 (2) |
C6A—N1A—C2A—N2A | −179.09 (17) | C4A—C5A—C7A—C8A | −94.5 (2) |
C2A—N1A—C6A—C5A | −2.7 (3) | C6A—C5A—C7A—C8A | 86.3 (2) |
C6A—N1A—C2A—N3A | 1.6 (3) | C5A—C7A—C8A—C13A | −26.8 (2) |
C2A—N3A—C4A—N4A | 178.40 (16) | C5A—C7A—C8A—C9A | 158.37 (17) |
C2A—N3A—C4A—C5A | −2.2 (2) | C13A—C8A—C9A—C10A | −1.2 (3) |
C4A—N3A—C2A—N1A | 0.7 (2) | C7A—C8A—C13A—C12A | −173.37 (15) |
C4A—N3A—C2A—N2A | −178.49 (16) | C7A—C8A—C9A—C10A | 173.67 (19) |
N3—C4—C5—C7 | −179.55 (16) | C9A—C8A—C13A—C12A | 1.3 (2) |
N3—C4—C5—C6 | −0.1 (2) | C8A—C9A—C10A—C11A | −0.1 (3) |
N4—C4—C5—C6 | 179.96 (17) | C8A—C9A—C10A—O3A | 179.34 (18) |
N4—C4—C5—C7 | 0.5 (3) | C9A—C10A—C11A—O4A | 177.54 (18) |
C6—C5—C7—C8 | 107.2 (2) | O3A—C10A—C11A—C12A | −178.17 (15) |
C4—C5—C6—N1 | 0.1 (3) | O3A—C10A—C11A—O4A | −1.9 (3) |
C7—C5—C6—N1 | 179.54 (17) | C9A—C10A—C11A—C12A | 1.3 (3) |
C4—C5—C7—C8 | −73.3 (2) | O4A—C11A—C12A—O5A | 2.3 (2) |
C5—C7—C8—C9 | 120.65 (17) | O4A—C11A—C12A—C13A | −177.52 (14) |
C5—C7—C8—C13 | −62.3 (2) | C10A—C11A—C12A—O5A | 178.62 (16) |
C9—C8—C13—C12 | −0.7 (2) | C10A—C11A—C12A—C13A | −1.2 (2) |
C7—C8—C13—C12 | −177.69 (15) | O5A—C12A—C13A—C8A | −179.87 (15) |
C7—C8—C9—C10 | 178.34 (15) | C11A—C12A—C13A—C8A | 0.0 (2) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, −y+1, −z; (iv) x−1, y, z; (v) −x, y−1/2, −z+1/2; (vi) x, −y+1/2, z+1/2; (vii) x+1, y, z; (viii) x, −y+1/2, z−1/2; (ix) −x+1, y+1/2, −z+1/2; (x) −x−1, −y+1, −z+1; (xi) −x+2, −y+1, −z; (xii) x+1, −y+1/2, z−1/2; (xiii) x−1, −y+1/2, z+1/2; (xiv) −x+1, y−1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O6i | 0.86 (2) | 1.80 (2) | 2.654 (2) | 172 (2) |
O1′—H1′···O3′ | 0.88 (2) | 1.87 (2) | 2.737 (2) | 170.3 (18) |
O1′—H2′···O6v | 0.91 (3) | 2.42 (3) | 3.121 (2) | 133 (3) |
O1′—H2′···O8v | 0.91 (3) | 1.90 (3) | 2.781 (2) | 160 (3) |
O2′—H3′···O9 | 0.72 (3) | 2.33 (3) | 3.045 (2) | 169 (3) |
O2′—H4′···O8vii | 0.89 (3) | 2.03 (3) | 2.900 (3) | 167 (3) |
O3′—H5′···O3 | 1.02 (4) | 1.83 (4) | 2.828 (2) | 166 (3) |
O3′—H6′···O4Aiv | 1.05 (5) | 1.76 (5) | 2.778 (2) | 162 (4) |
N2A—H8···O1′viii | 0.83 (2) | 2.06 (2) | 2.818 (3) | 152 (2) |
N4—H21···O2′iv | 0.87 (3) | 2.15 (3) | 2.974 (3) | 157 (2) |
N4A—H22···N3Axi | 0.91 (2) | 2.25 (2) | 3.155 (2) | 173.1 (18) |
N2A—H23···O9iii | 0.92 (3) | 1.96 (3) | 2.826 (2) | 156 (2) |
N4A—H27···O8vii | 0.90 (2) | 2.24 (2) | 3.105 (2) | 161 (2) |
N4—H30···O7 | 0.88 (2) | 2.00 (2) | 2.826 (2) | 155 (2) |
N1A—H37···O1′viii | 0.85 (2) | 2.00 (2) | 2.778 (2) | 152 (2) |
N1A—H37···O4viii | 0.85 (2) | 2.58 (2) | 3.090 (2) | 120.1 (19) |
N2—H40···N3x | 0.86 (2) | 2.23 (2) | 3.080 (2) | 176 (2) |
N2—H41···O2′i | 0.85 (2) | 2.33 (2) | 3.038 (3) | 140 (2) |
C7A—H3···O8vii | 0.96 (2) | 2.38 (2) | 3.295 (3) | 158.5 (17) |
C6A—H7···O4viii | 0.95 (2) | 2.51 (2) | 3.131 (2) | 123.2 (14) |
C6A—H7···O5viii | 0.95 (2) | 2.46 (2) | 3.363 (2) | 158.3 (17) |
C9—H15···O7 | 0.93 (2) | 2.31 (2) | 3.131 (2) | 146.7 (18) |
C15—H33···O3Aiv | 0.97 (2) | 2.59 (2) | 3.537 (3) | 167 (2) |
Symmetry codes: (i) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z; (iv) x−1, y, z; (v) −x, y−1/2, −z+1/2; (vii) x+1, y, z; (viii) x, −y+1/2, z−1/2; (x) −x−1, −y+1, −z+1; (xi) −x+2, −y+1, −z. |
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