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Pyrroloquinoline quinone (PQQ) is a water-soluble quinone compound first identified as a cofactor of alcohol- and glucose-dehydrogenases (ADH and GDH) in bacteria. For example, in the process of ADH reaction, alcohol is oxidized to the corresponding aldehyde, and inversely PQQ is reduced to pyrroloquinoline quinol (PQQH2). PQQ and PQQH2 molecules play an important role as a cofactor in ADH and GDH reactions. However, crystal structure analysis has not been performed for PQQ and PQQH2. In the present study, the synthesis of PQQH2 powder crystals was performed under air, by utilizing vitamin C as a reducing agent. By reacting a trihydrate of disodium salt of PQQ (PQQNa2·3H2O) with excess vitamin C in H2O at 293 and 343 K, yellowish brown and black powder crystals of PQQH2 having different properties were obtained in high yield, respectively. The former was PQQH2 trihydrate (PQQH2·3H2O) and the latter was PQQH2 anhydrate (PQQH2). Furthermore, sodium-free red PQQ powder crystal (a monohydrate of PQQ, PQQ·H2O) was prepared by the reaction of PQQNa2·3H2O with HCl in H2O. Single crystals of PQQH2 and PQQ were prepared from Me2SO/CH3CN mixed solvent, and we have succeeded in the crystal structure analyses of PQQH2 and PQQ for the first time.
Supporting information
CCDC references: 1487730; 1487731
For both compounds, data collection: CrystalClear (Rigaku Inc., 2008); cell refinement: CrystalClear (Rigaku Inc., 2008); data reduction: CrystalClear (Rigaku Inc., 2008); program(s) used to solve structure: SIR2011 (Burla, et al., 2012); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2016); molecular graphics: CrystalStructure 4.2.4 (Rigaku, 2016); software used to prepare material for publication: CrystalStructure 4.2.4 (Rigaku, 2016).
Crystal data top
2(C7H4NO4)·2(C2H6OS)·C2H3N | Dx = 1.536 Mg m−3 |
Mr = 529.53 | Mo Kα radiation, λ = 0.71075 Å |
Orthorhombic, Pnma | Cell parameters from 6974 reflections |
a = 14.563 (5) Å | θ = 2.2–31.2° |
b = 6.748 (2) Å | µ = 0.30 mm−1 |
c = 23.299 (9) Å | T = 100 K |
V = 2289.6 (14) Å3 | Needle, orange |
Z = 4 | 0.24 × 0.03 × 0.02 mm |
F(000) = 1104 | |
Data collection top
Rigaku Saturn724 diffractometer | 2990 independent reflections |
Radiation source: Varimax 50 kV 24 mA Rotating anode | 2846 reflections with I > 2σ(I) |
Detector resolution: 7.111 pixels mm-1 | Rint = 0.051 |
ω scans | θmax = 28.0°, θmin = 2.2° |
Absorption correction: multi-scan REQAB (Rigaku, 1998) | h = −19→19 |
Tmin = 0.912, Tmax = 0.994 | k = −8→8 |
38156 measured reflections | l = −30→30 |
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)] = 0.060 | Hydrogen site location: mixed |
wR(F2) = 0.134 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.053P)2 + 3.2P] where P = (Fo2 + 2Fc2)/3 |
2990 reflections | (Δ/σ)max = 0.001 |
267 parameters | Δρmax = 0.48 e Å−3 |
236 restraints | Δρmin = −0.36 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.95984 (15) | 0.250000 | 0.25191 (9) | 0.0413 (6) | |
O2 | 1.11256 (15) | 0.250000 | 0.25846 (9) | 0.0310 (5) | |
H2O | 1.099 (3) | 0.250000 | 0.2922 (18) | 0.037* | |
O3 | 1.23564 (13) | 0.250000 | 0.02383 (9) | 0.0251 (5) | |
H3O | 1.257 (2) | 0.250000 | −0.0141 (16) | 0.030* | |
O4 | 1.14103 (14) | 0.250000 | −0.07778 (9) | 0.0290 (5) | |
H4O | 1.110 (3) | 0.250000 | −0.1046 (17) | 0.035* | |
O5 | 0.74435 (14) | 0.250000 | −0.15150 (9) | 0.0316 (5) | |
O6 | 0.88455 (14) | 0.250000 | −0.18742 (8) | 0.0246 (4) | |
H6O | 0.945 (3) | 0.250000 | −0.1763 (16) | 0.030* | |
O7 | 0.79196 (14) | 0.250000 | 0.11706 (8) | 0.0301 (5) | |
O8 | 0.68979 (15) | 0.250000 | 0.04710 (9) | 0.0430 (7) | |
H8O | 0.654 (3) | 0.250000 | 0.076 (2) | 0.052* | |
N1 | 0.97079 (16) | 0.250000 | 0.13227 (9) | 0.0195 (5) | |
H1N | 0.913 (2) | 0.250000 | 0.1430 (15) | 0.023* | |
C2 | 1.04677 (19) | 0.250000 | 0.16660 (11) | 0.0207 (5) | |
C3 | 1.12426 (18) | 0.250000 | 0.13281 (11) | 0.0197 (5) | |
H3 | 1.186186 | 0.250000 | 0.145626 | 0.024* | |
C3A | 1.09347 (17) | 0.250000 | 0.07514 (11) | 0.0178 (5) | |
C4 | 1.14201 (18) | 0.250000 | 0.02226 (12) | 0.0199 (5) | |
C5 | 1.09317 (18) | 0.250000 | −0.02786 (11) | 0.0188 (5) | |
C5A | 0.99512 (18) | 0.250000 | −0.02736 (11) | 0.0165 (5) | |
N6 | 0.95695 (15) | 0.250000 | −0.08022 (9) | 0.0171 (4) | |
C7 | 0.86636 (18) | 0.250000 | −0.08423 (11) | 0.0182 (5) | |
C8 | 0.80810 (18) | 0.250000 | −0.03693 (11) | 0.0190 (5) | |
H8 | 0.743438 | 0.250000 | −0.042315 | 0.023* | |
C9 | 0.84439 (18) | 0.250000 | 0.01811 (11) | 0.0169 (5) | |
C9A | 0.94206 (18) | 0.250000 | 0.02498 (11) | 0.0169 (5) | |
C1A | 0.99642 (18) | 0.250000 | 0.07598 (11) | 0.0169 (5) | |
C10 | 1.0344 (2) | 0.250000 | 0.22905 (12) | 0.0241 (6) | |
C11 | 0.82666 (19) | 0.250000 | −0.14344 (11) | 0.0216 (6) | |
C12 | 0.77507 (18) | 0.250000 | 0.06616 (12) | 0.0218 (6) | |
S1S | 1.13174 (5) | 0.250000 | −0.23528 (3) | 0.0292 (2) | |
C1S | 1.20922 (16) | 0.4481 (4) | −0.22216 (10) | 0.0391 (6) | |
H1SA | 1.231636 | 0.440347 | −0.182567 | 0.047* | |
H1SB | 1.177551 | 0.574682 | −0.227969 | 0.047* | |
H1SC | 1.261229 | 0.438661 | −0.248715 | 0.047* | |
O1S | 1.06649 (16) | 0.250000 | −0.18464 (10) | 0.0490 (8) | |
S2S | 0.46451 (11) | 0.3252 (3) | 0.11996 (11) | 0.0298 (4) | 0.3586 (15) |
C2SA | 0.4619 (5) | 0.3930 (14) | 0.0459 (3) | 0.0472 (19) | 0.3586 (15) |
H2SA | 0.483050 | 0.530048 | 0.041575 | 0.071* | 0.3586 (15) |
H2SB | 0.398899 | 0.381654 | 0.031369 | 0.071* | 0.3586 (15) |
H2SC | 0.502147 | 0.304519 | 0.024005 | 0.071* | 0.3586 (15) |
C2SB | 0.3990 (12) | 0.105 (2) | 0.1158 (7) | 0.040 (3) | 0.3586 (15) |
H2SD | 0.436074 | −0.000002 | 0.098375 | 0.060* | 0.3586 (15) |
H2SE | 0.344287 | 0.128674 | 0.092247 | 0.060* | 0.3586 (15) |
H2SF | 0.380215 | 0.064818 | 0.154468 | 0.060* | 0.3586 (15) |
O2S | 0.56169 (16) | 0.230 (2) | 0.12930 (11) | 0.0312 (14) | 0.3586 (15) |
S3S | 0.4719 (2) | 0.250000 | 0.08417 (17) | 0.0343 (9) | 0.244 (2) |
C3S | 0.3985 (19) | 0.058 (3) | 0.1078 (12) | 0.035 (4) | 0.244 (2) |
H3SA | 0.407724 | −0.059548 | 0.083778 | 0.052* | 0.244 (2) |
H3SB | 0.334506 | 0.101626 | 0.104859 | 0.052* | 0.244 (2) |
H3SC | 0.412674 | 0.025548 | 0.147816 | 0.052* | 0.244 (2) |
O3S | 0.56169 (16) | 0.230 (2) | 0.12930 (11) | 0.0312 (14) | 0.1221 (12) |
S4S | 0.4585 (15) | 0.250000 | 0.120 (2) | 0.034 (3) | 0.039 (3) |
C4S | 0.415 (4) | 0.439 (9) | 0.072 (3) | 0.038 (6) | 0.039 (3) |
H4SA | 0.435174 | 0.569824 | 0.086014 | 0.057* | 0.039 (3) |
H4SB | 0.348115 | 0.434026 | 0.071526 | 0.057* | 0.039 (3) |
H4SC | 0.439364 | 0.416935 | 0.033572 | 0.057* | 0.039 (3) |
O4S | 0.56169 (16) | 0.230 (2) | 0.12930 (11) | 0.0312 (14) | 0.0193 (14) |
N1S | 1.3585 (2) | 0.250000 | −0.07550 (13) | 0.0440 (8) | |
C5S | 1.3906 (2) | 0.250000 | −0.11983 (14) | 0.0360 (8) | |
C6S | 1.4333 (2) | 0.250000 | −0.17659 (14) | 0.0401 (9) | |
H6SA | 1.432224 | 0.115440 | −0.192397 | 0.060* | 0.5 |
H6SB | 1.497004 | 0.295357 | −0.173343 | 0.060* | 0.5 |
H6SC | 1.399285 | 0.339203 | −0.202085 | 0.060* | 0.5 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0236 (11) | 0.083 (2) | 0.0178 (10) | 0.000 | −0.0041 (8) | 0.000 |
O2 | 0.0229 (10) | 0.0516 (14) | 0.0184 (10) | 0.000 | −0.0074 (8) | 0.000 |
O3 | 0.0125 (9) | 0.0402 (12) | 0.0227 (10) | 0.000 | −0.0007 (7) | 0.000 |
O4 | 0.0178 (10) | 0.0528 (15) | 0.0163 (9) | 0.000 | 0.0032 (7) | 0.000 |
O5 | 0.0195 (10) | 0.0566 (15) | 0.0188 (10) | 0.000 | −0.0025 (8) | 0.000 |
O6 | 0.0222 (10) | 0.0373 (12) | 0.0143 (9) | 0.000 | 0.0000 (7) | 0.000 |
O7 | 0.0202 (10) | 0.0563 (15) | 0.0138 (9) | 0.000 | −0.0008 (7) | 0.000 |
O8 | 0.0172 (10) | 0.095 (2) | 0.0171 (10) | 0.000 | 0.0027 (8) | 0.000 |
N1 | 0.0159 (11) | 0.0295 (13) | 0.0131 (10) | 0.000 | −0.0021 (8) | 0.000 |
C2 | 0.0208 (13) | 0.0263 (14) | 0.0151 (12) | 0.000 | −0.0052 (10) | 0.000 |
C3 | 0.0181 (12) | 0.0214 (13) | 0.0197 (12) | 0.000 | −0.0066 (10) | 0.000 |
C3A | 0.0160 (12) | 0.0188 (13) | 0.0185 (12) | 0.000 | −0.0024 (9) | 0.000 |
C4 | 0.0153 (12) | 0.0219 (13) | 0.0223 (13) | 0.000 | −0.0016 (10) | 0.000 |
C5 | 0.0155 (12) | 0.0238 (14) | 0.0170 (12) | 0.000 | 0.0017 (9) | 0.000 |
C5A | 0.0170 (12) | 0.0170 (12) | 0.0157 (11) | 0.000 | −0.0007 (9) | 0.000 |
N6 | 0.0184 (10) | 0.0195 (11) | 0.0134 (10) | 0.000 | −0.0012 (8) | 0.000 |
C7 | 0.0181 (12) | 0.0209 (13) | 0.0157 (12) | 0.000 | −0.0023 (9) | 0.000 |
C8 | 0.0161 (12) | 0.0224 (13) | 0.0184 (12) | 0.000 | −0.0024 (9) | 0.000 |
C9 | 0.0172 (12) | 0.0187 (12) | 0.0148 (11) | 0.000 | 0.0000 (9) | 0.000 |
C9A | 0.0175 (12) | 0.0177 (12) | 0.0156 (12) | 0.000 | −0.0015 (9) | 0.000 |
C1A | 0.0189 (12) | 0.0168 (12) | 0.0151 (11) | 0.000 | −0.0027 (9) | 0.000 |
C10 | 0.0234 (13) | 0.0315 (15) | 0.0174 (12) | 0.000 | −0.0044 (10) | 0.000 |
C11 | 0.0195 (12) | 0.0296 (15) | 0.0157 (12) | 0.000 | 0.0006 (10) | 0.000 |
C12 | 0.0163 (12) | 0.0295 (15) | 0.0197 (12) | 0.000 | −0.0002 (10) | 0.000 |
S1S | 0.0175 (3) | 0.0544 (5) | 0.0159 (3) | 0.000 | 0.0012 (2) | 0.000 |
C1S | 0.0306 (11) | 0.0483 (15) | 0.0382 (12) | 0.0033 (11) | 0.0020 (9) | −0.0138 (11) |
O1S | 0.0205 (11) | 0.108 (2) | 0.0187 (11) | 0.000 | 0.0036 (9) | 0.000 |
S2S | 0.0205 (7) | 0.0445 (9) | 0.0243 (8) | −0.0046 (7) | −0.0048 (6) | 0.0045 (11) |
C2SA | 0.040 (3) | 0.073 (5) | 0.029 (3) | −0.019 (3) | −0.016 (3) | 0.026 (3) |
C2SB | 0.017 (4) | 0.068 (7) | 0.036 (5) | −0.010 (5) | −0.012 (3) | 0.003 (5) |
O2S | 0.0175 (10) | 0.051 (4) | 0.0252 (10) | −0.001 (2) | 0.0026 (8) | 0.000 (2) |
S3S | 0.0211 (14) | 0.052 (2) | 0.0296 (19) | 0.000 | −0.0010 (12) | 0.000 |
C3S | 0.026 (6) | 0.039 (7) | 0.040 (8) | −0.010 (5) | −0.013 (5) | −0.004 (5) |
O3S | 0.0175 (10) | 0.051 (4) | 0.0252 (10) | −0.001 (2) | 0.0026 (8) | 0.000 (2) |
S4S | 0.026 (4) | 0.049 (5) | 0.028 (5) | 0.000 | −0.005 (4) | 0.000 |
C4S | 0.032 (9) | 0.051 (10) | 0.032 (9) | −0.005 (9) | −0.005 (9) | 0.003 (9) |
O4S | 0.0175 (10) | 0.051 (4) | 0.0252 (10) | −0.001 (2) | 0.0026 (8) | 0.000 (2) |
N1S | 0.0285 (14) | 0.075 (2) | 0.0284 (14) | 0.000 | 0.0039 (12) | 0.000 |
C5S | 0.0232 (14) | 0.059 (2) | 0.0261 (15) | 0.000 | −0.0015 (12) | 0.000 |
C6S | 0.0293 (16) | 0.067 (3) | 0.0243 (15) | 0.000 | 0.0032 (13) | 0.000 |
Geometric parameters (Å, º) top
O1—C10 | 1.209 (4) | S1S—C1Si | 1.776 (3) |
O2—C10 | 1.329 (3) | C1S—H1SA | 0.9800 |
O2—H2O | 0.81 (4) | C1S—H1SB | 0.9800 |
O3—C4 | 1.364 (3) | C1S—H1SC | 0.9800 |
O3—H3O | 0.94 (4) | S2S—O2S | 1.569 (6) |
O4—C5 | 1.356 (3) | S2S—C2SB | 1.768 (11) |
O4—H4O | 0.77 (4) | S2S—C2SA | 1.786 (6) |
O5—C11 | 1.213 (3) | C2SA—H2SA | 0.9800 |
O6—C11 | 1.327 (3) | C2SA—H2SB | 0.9800 |
O6—H6O | 0.91 (4) | C2SA—H2SC | 0.9800 |
O7—C12 | 1.211 (3) | C2SB—H2SD | 0.9800 |
O8—C12 | 1.319 (3) | C2SB—H2SE | 0.9800 |
O8—H8O | 0.86 (5) | C2SB—H2SF | 0.9800 |
N1—C1A | 1.364 (3) | S3S—O3S | 1.684 (4) |
N1—C2 | 1.365 (3) | S3S—O3Si | 1.684 (4) |
N1—H1N | 0.88 (4) | S3S—C3S | 1.767 (16) |
C2—C3 | 1.376 (4) | S3S—C3Si | 1.767 (16) |
C2—C10 | 1.466 (4) | C3S—H3SA | 0.9800 |
C3—C3A | 1.417 (4) | C3S—H3SB | 0.9800 |
C3—H3 | 0.9500 | C3S—H3SC | 0.9800 |
C3A—C1A | 1.413 (4) | O3S—O3Si | 0.27 (3) |
C3A—C4 | 1.420 (4) | S4S—O4S | 1.525 (19) |
C4—C5 | 1.367 (4) | S4S—C4Si | 1.81 (2) |
C5—C5A | 1.428 (4) | S4S—C4S | 1.81 (2) |
C5A—N6 | 1.351 (3) | C4S—H4SA | 0.9800 |
C5A—C9A | 1.444 (3) | C4S—H4SB | 0.9800 |
N6—C7 | 1.322 (3) | C4S—H4SC | 0.9800 |
C7—C8 | 1.391 (4) | N1S—C5S | 1.133 (4) |
C7—C11 | 1.496 (4) | C5S—C6S | 1.462 (4) |
C8—C9 | 1.387 (3) | C6S—H6SA | 0.9800 |
C8—H8 | 0.9500 | C6S—H6SB | 0.9800 |
C9—C9A | 1.431 (4) | C6S—H6SC | 0.9800 |
C9—C12 | 1.508 (4) | C6S—H6SAi | 0.980 (11) |
C9A—C1A | 1.428 (3) | C6S—H6SBi | 0.98 (2) |
S1S—O1S | 1.515 (2) | C6S—H6SCi | 0.98 (3) |
S1S—C1S | 1.776 (3) | | |
| | | |
C10—O2—H2O | 107 (3) | S1S—C1S—H1SC | 109.5 |
C4—O3—H3O | 108 (2) | H1SA—C1S—H1SC | 109.5 |
C5—O4—H4O | 113 (3) | H1SB—C1S—H1SC | 109.5 |
C11—O6—H6O | 113 (2) | O2S—S2S—C2SB | 98.7 (8) |
C12—O8—H8O | 108 (3) | O2S—S2S—C2SA | 105.0 (3) |
C1A—N1—C2 | 110.0 (2) | C2SB—S2S—C2SA | 98.6 (6) |
C1A—N1—H1N | 122 (2) | S2S—C2SA—H2SA | 109.5 |
C2—N1—H1N | 128 (2) | S2S—C2SA—H2SB | 109.5 |
N1—C2—C3 | 109.2 (2) | H2SA—C2SA—H2SB | 109.5 |
N1—C2—C10 | 118.8 (2) | S2S—C2SA—H2SC | 109.5 |
C3—C2—C10 | 132.0 (2) | H2SA—C2SA—H2SC | 109.5 |
C2—C3—C3A | 106.4 (2) | H2SB—C2SA—H2SC | 109.5 |
C2—C3—H3 | 126.8 | S2S—C2SB—H2SD | 109.5 |
C3A—C3—H3 | 126.8 | S2S—C2SB—H2SE | 109.5 |
C1A—C3A—C3 | 107.7 (2) | H2SD—C2SB—H2SE | 109.5 |
C1A—C3A—C4 | 120.6 (2) | S2S—C2SB—H2SF | 109.5 |
C3—C3A—C4 | 131.7 (2) | H2SD—C2SB—H2SF | 109.5 |
O3—C4—C5 | 122.9 (2) | H2SE—C2SB—H2SF | 109.5 |
O3—C4—C3A | 118.3 (2) | O3S—S3S—C3S | 102.6 (11) |
C5—C4—C3A | 118.8 (2) | O3Si—S3S—C3S | 109.5 (11) |
O4—C5—C4 | 117.7 (2) | S3S—C3S—H3SA | 109.5 |
O4—C5—C5A | 121.4 (2) | S3S—C3S—H3SB | 109.5 |
C4—C5—C5A | 120.9 (2) | H3SA—C3S—H3SB | 109.5 |
N6—C5A—C5 | 113.8 (2) | S3S—C3S—H3SC | 109.5 |
N6—C5A—C9A | 123.3 (2) | H3SA—C3S—H3SC | 109.5 |
C5—C5A—C9A | 122.8 (2) | H3SB—C3S—H3SC | 109.5 |
C7—N6—C5A | 118.4 (2) | O3Si—O3S—S3S | 85.5 (5) |
N6—C7—C8 | 123.5 (2) | O4S—S4S—C4S | 119 (3) |
N6—C7—C11 | 116.8 (2) | C4Si—S4S—C4S | 90 (5) |
C8—C7—C11 | 119.7 (2) | S4S—C4S—H4SA | 109.5 |
C9—C8—C7 | 120.0 (2) | S4S—C4S—H4SB | 109.5 |
C9—C8—H8 | 120.0 | H4SA—C4S—H4SB | 109.5 |
C7—C8—H8 | 120.0 | S4S—C4S—H4SC | 109.5 |
C8—C9—C9A | 118.8 (2) | H4SA—C4S—H4SC | 109.5 |
C8—C9—C12 | 115.6 (2) | H4SB—C4S—H4SC | 109.5 |
C9A—C9—C12 | 125.6 (2) | N1S—C5S—C6S | 179.1 (4) |
C1A—C9A—C9 | 130.1 (2) | C5S—C6S—H6SA | 109.5 |
C1A—C9A—C5A | 114.0 (2) | C5S—C6S—H6SB | 109.5 |
C9—C9A—C5A | 115.9 (2) | H6SA—C6S—H6SB | 109.5 |
N1—C1A—C3A | 106.7 (2) | C5S—C6S—H6SC | 109.5 |
N1—C1A—C9A | 130.4 (2) | H6SA—C6S—H6SC | 109.5 |
C3A—C1A—C9A | 122.9 (2) | H6SB—C6S—H6SC | 109.5 |
O1—C10—O2 | 122.8 (3) | C5S—C6S—H6SAi | 109.5 (2) |
O1—C10—C2 | 123.2 (3) | H6SA—C6S—H6SAi | 135.8 |
O2—C10—C2 | 114.0 (2) | H6SB—C6S—H6SAi | 75.8 |
O5—C11—O6 | 120.5 (2) | H6SC—C6S—H6SAi | 36.4 |
O5—C11—C7 | 121.6 (2) | C5S—C6S—H6SBi | 109.5 (4) |
O6—C11—C7 | 117.8 (2) | H6SA—C6S—H6SBi | 75.8 |
O7—C12—O8 | 121.4 (3) | H6SB—C6S—H6SBi | 36.4 |
O7—C12—C9 | 126.2 (2) | H6SC—C6S—H6SBi | 135.8 |
O8—C12—C9 | 112.4 (2) | H6SAi—C6S—H6SBi | 109.5 |
O1S—S1S—C1S | 105.34 (10) | C5S—C6S—H6SCi | 109.5 (7) |
O1S—S1S—C1Si | 105.34 (10) | H6SA—C6S—H6SCi | 36.4 |
C1S—S1S—C1Si | 97.67 (17) | H6SB—C6S—H6SCi | 135.8 |
S1S—C1S—H1SA | 109.5 | H6SC—C6S—H6SCi | 75.8 |
S1S—C1S—H1SB | 109.5 | H6SAi—C6S—H6SCi | 109.5 |
H1SA—C1S—H1SB | 109.5 | H6SBi—C6S—H6SCi | 109.5 |
| | | |
C1A—N1—C2—C3 | 0.000 (1) | C12—C9—C9A—C5A | 180.0 |
C1A—N1—C2—C10 | 180.000 (1) | N6—C5A—C9A—C1A | 180.0 |
N1—C2—C3—C3A | 0.000 (1) | C5—C5A—C9A—C1A | 0.0 |
C10—C2—C3—C3A | 180.000 (1) | N6—C5A—C9A—C9 | 0.0 |
C2—C3—C3A—C1A | 0.000 (1) | C5—C5A—C9A—C9 | 180.0 |
C2—C3—C3A—C4 | 180.000 (1) | C2—N1—C1A—C3A | 0.000 (1) |
C1A—C3A—C4—O3 | 180.0 | C2—N1—C1A—C9A | 180.000 (1) |
C3—C3A—C4—O3 | 0.000 (1) | C3—C3A—C1A—N1 | 0.000 (1) |
C1A—C3A—C4—C5 | 0.0 | C4—C3A—C1A—N1 | 180.000 (1) |
C3—C3A—C4—C5 | 180.000 (1) | C3—C3A—C1A—C9A | 180.000 (1) |
O3—C4—C5—O4 | 0.0 | C4—C3A—C1A—C9A | 0.000 (1) |
C3A—C4—C5—O4 | 180.0 | C9—C9A—C1A—N1 | 0.000 (1) |
O3—C4—C5—C5A | 180.0 | C5A—C9A—C1A—N1 | 180.0 |
C3A—C4—C5—C5A | 0.0 | C9—C9A—C1A—C3A | 180.0 |
O4—C5—C5A—N6 | 0.0 | C5A—C9A—C1A—C3A | 0.0 |
C4—C5—C5A—N6 | 180.0 | N1—C2—C10—O1 | 0.000 (1) |
O4—C5—C5A—C9A | 180.0 | C3—C2—C10—O1 | 180.000 (1) |
C4—C5—C5A—C9A | 0.0 | N1—C2—C10—O2 | 180.000 (1) |
C5—C5A—N6—C7 | 180.0 | C3—C2—C10—O2 | 0.000 (1) |
C9A—C5A—N6—C7 | 0.0 | N6—C7—C11—O5 | 180.000 (1) |
C5A—N6—C7—C8 | 0.000 (1) | C8—C7—C11—O5 | 0.000 (1) |
C5A—N6—C7—C11 | 180.000 (1) | N6—C7—C11—O6 | 0.000 (1) |
N6—C7—C8—C9 | 0.0 | C8—C7—C11—O6 | 180.000 (1) |
C11—C7—C8—C9 | 180.000 (1) | C8—C9—C12—O7 | 180.0 |
C7—C8—C9—C9A | 0.0 | C9A—C9—C12—O7 | 0.0 |
C7—C8—C9—C12 | 180.0 | C8—C9—C12—O8 | 0.0 |
C8—C9—C9A—C1A | 180.0 | C9A—C9—C12—O8 | 180.0 |
C12—C9—C9A—C1A | 0.0 | C3S—S3S—O3S—O3Si | −140.5 (8) |
C8—C9—C9A—C5A | 0.0 | C3Si—S3S—O3S—O3Si | −41.2 (9) |
Symmetry code: (i) x, −y+1/2, z. |
Crystal data top
C14H6N2O8·3(C2H6OS) | Dx = 1.532 Mg m−3 |
Mr = 564.59 | Mo Kα radiation, λ = 0.71075 Å |
Orthorhombic, P212121 | Cell parameters from 7223 reflections |
a = 6.901 (5) Å | θ = 2.2–31.3° |
b = 12.371 (8) Å | µ = 0.37 mm−1 |
c = 28.674 (18) Å | T = 100 K |
V = 2448 (3) Å3 | Block, orange |
Z = 4 | 0.05 × 0.05 × 0.02 mm |
F(000) = 1176 | |
Data collection top
Rigaku Saturn724 diffractometer | 5885 independent reflections |
Radiation source: Varimax 50 kV 24 mA Rotating anode | 4968 reflections with I > 2σ(I) |
Detector resolution: 7.111 pixels mm-1 | Rint = 0.077 |
ω scans | θmax = 28.0°, θmin = 2.2° |
Absorption correction: multi-scan REQAB (Rigaku, 1998) | h = −9→9 |
Tmin = 0.910, Tmax = 0.993 | k = −16→16 |
41911 measured reflections | l = −37→37 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.070 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.185 | w = 1/[σ2(Fo2) + (0.0801P)2 + 4.9734P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
5885 reflections | Δρmax = 1.43 e Å−3 |
337 parameters | Δρmin = −0.78 e Å−3 |
0 restraints | Absolute structure: Flack x determined using 1648 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.12 (3) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.9440 (7) | 0.8466 (4) | −0.05934 (17) | 0.0218 (10) | |
H1N | 0.914 (10) | 0.906 (6) | −0.039 (2) | 0.026* | |
C2 | 0.9653 (9) | 0.8499 (4) | −0.10737 (18) | 0.0218 (11) | |
C3 | 0.9869 (9) | 0.7459 (4) | −0.12347 (17) | 0.0206 (10) | |
H3 | 1.004371 | 0.724012 | −0.154950 | 0.025* | |
C3A | 0.9777 (8) | 0.6775 (4) | −0.08356 (17) | 0.0190 (10) | |
C4 | 0.9825 (9) | 0.5605 (4) | −0.08101 (17) | 0.0203 (10) | |
C5 | 0.9453 (8) | 0.5134 (4) | −0.03123 (19) | 0.0220 (11) | |
C5A | 0.9399 (8) | 0.5897 (4) | 0.01008 (18) | 0.0194 (10) | |
N6 | 0.9387 (7) | 0.5391 (4) | 0.05150 (16) | 0.0218 (9) | |
C7 | 0.9494 (8) | 0.6010 (4) | 0.08993 (18) | 0.0204 (11) | |
C8 | 0.9599 (8) | 0.7140 (4) | 0.08793 (19) | 0.0215 (11) | |
H8 | 0.972814 | 0.754651 | 0.115863 | 0.026* | |
C9 | 0.9516 (8) | 0.7667 (4) | 0.04513 (19) | 0.0210 (11) | |
C9A | 0.9441 (8) | 0.7031 (4) | 0.00378 (19) | 0.0194 (10) | |
C1A | 0.9501 (8) | 0.7430 (4) | −0.04392 (19) | 0.0209 (11) | |
C10 | 0.9588 (9) | 0.9563 (5) | −0.1305 (2) | 0.0276 (13) | |
C11 | 0.9544 (9) | 0.5438 (5) | 0.13669 (19) | 0.0264 (13) | |
C12 | 0.9484 (8) | 0.8898 (4) | 0.04803 (19) | 0.0216 (11) | |
O1 | 0.9249 (9) | 1.0384 (4) | −0.10878 (17) | 0.0431 (13) | |
O2 | 0.9909 (8) | 0.9506 (3) | −0.17610 (13) | 0.0281 (8) | |
H2O | 0.990325 | 1.013111 | −0.187500 | 0.042* | |
O3 | 1.0089 (8) | 0.4989 (3) | −0.11352 (13) | 0.0288 (9) | |
O4 | 0.9196 (7) | 0.4173 (3) | −0.02732 (15) | 0.0274 (9) | |
O5 | 0.9234 (8) | 0.4468 (3) | 0.14038 (15) | 0.0332 (11) | |
O6 | 0.9905 (8) | 0.6094 (3) | 0.17141 (13) | 0.0291 (9) | |
H6O | 0.990604 | 0.574423 | 0.196522 | 0.044* | |
O7 | 0.8509 (6) | 0.9449 (3) | 0.02061 (14) | 0.0257 (9) | |
O8 | 1.0449 (7) | 0.9278 (3) | 0.08221 (15) | 0.0318 (11) | |
H8O | 1.001782 | 0.989128 | 0.089298 | 0.048* | |
S1S | 0.9985 (3) | 1.23776 (12) | −0.17812 (5) | 0.0329 (4) | |
C1SA | 0.8146 (18) | 1.3285 (11) | −0.1955 (5) | 0.108 (6) | |
H1SA | 0.688111 | 1.300080 | −0.186011 | 0.130* | |
H1SB | 0.817547 | 1.336838 | −0.229521 | 0.130* | |
H1SC | 0.836177 | 1.398896 | −0.180755 | 0.130* | |
C1SB | 1.1942 (17) | 1.3168 (10) | −0.1962 (5) | 0.092 (5) | |
H1SD | 1.175788 | 1.338065 | −0.228833 | 0.111* | |
H1SE | 1.314305 | 1.275098 | −0.193257 | 0.111* | |
H1SF | 1.202378 | 1.381684 | −0.176680 | 0.111* | |
O1S | 0.9905 (8) | 1.1426 (3) | −0.21235 (13) | 0.0329 (10) | |
S2S | 1.0039 (3) | 0.40255 (14) | 0.25892 (5) | 0.0349 (4) | |
C2SA | 0.8094 (11) | 0.3687 (7) | 0.2970 (3) | 0.0402 (18) | |
H2SA | 0.821868 | 0.409741 | 0.326042 | 0.048* | |
H2SB | 0.813356 | 0.291118 | 0.303868 | 0.048* | |
H2SC | 0.685925 | 0.386517 | 0.281949 | 0.048* | |
C2SB | 1.1931 (10) | 0.3767 (7) | 0.2993 (3) | 0.0385 (17) | |
H2SD | 1.174405 | 0.421349 | 0.327172 | 0.046* | |
H2SE | 1.318079 | 0.394221 | 0.284954 | 0.046* | |
H2SF | 1.191343 | 0.300123 | 0.308118 | 0.046* | |
O2S | 0.9969 (9) | 0.5214 (4) | 0.25197 (15) | 0.0396 (11) | |
S3S | 0.9899 (3) | 1.19353 (10) | 0.05375 (5) | 0.0253 (3) | |
C3SA | 0.7711 (10) | 1.2660 (6) | 0.0640 (2) | 0.0304 (14) | |
H3SA | 0.780417 | 1.304637 | 0.093730 | 0.036* | |
H3SB | 0.662183 | 1.215165 | 0.065177 | 0.036* | |
H3SC | 0.750100 | 1.317939 | 0.038695 | 0.036* | |
C3SB | 1.1622 (10) | 1.2955 (5) | 0.0647 (3) | 0.0321 (14) | |
H3SD | 1.292778 | 1.264513 | 0.063289 | 0.039* | |
H3SE | 1.139876 | 1.326264 | 0.095709 | 0.039* | |
H3SF | 1.149846 | 1.352457 | 0.041106 | 0.039* | |
O3S | 1.0051 (8) | 1.1197 (3) | 0.09775 (13) | 0.0292 (9) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.024 (2) | 0.017 (2) | 0.024 (2) | −0.0024 (18) | 0.0016 (18) | 0.0032 (18) |
C2 | 0.027 (3) | 0.017 (2) | 0.022 (2) | 0.001 (2) | −0.002 (2) | 0.0006 (19) |
C3 | 0.024 (3) | 0.019 (2) | 0.019 (2) | 0.000 (2) | 0.001 (2) | 0.0011 (18) |
C3A | 0.020 (3) | 0.019 (2) | 0.018 (2) | 0.002 (2) | −0.004 (2) | 0.0005 (18) |
C4 | 0.024 (3) | 0.019 (2) | 0.018 (2) | 0.001 (2) | −0.002 (2) | −0.0015 (18) |
C5 | 0.025 (3) | 0.018 (2) | 0.022 (3) | 0.002 (2) | −0.001 (2) | −0.002 (2) |
C5A | 0.020 (2) | 0.018 (2) | 0.020 (2) | −0.0003 (19) | 0.0008 (19) | 0.0016 (19) |
N6 | 0.024 (2) | 0.019 (2) | 0.023 (2) | −0.0022 (18) | −0.0005 (18) | 0.0005 (18) |
C7 | 0.023 (3) | 0.018 (2) | 0.020 (2) | 0.001 (2) | 0.000 (2) | 0.0023 (19) |
C8 | 0.022 (3) | 0.021 (2) | 0.022 (2) | −0.002 (2) | 0.005 (2) | −0.002 (2) |
C9 | 0.022 (3) | 0.018 (2) | 0.023 (3) | 0.001 (2) | −0.001 (2) | 0.000 (2) |
C9A | 0.017 (2) | 0.017 (2) | 0.024 (2) | 0.0007 (19) | 0.001 (2) | −0.003 (2) |
C1A | 0.023 (3) | 0.014 (2) | 0.025 (3) | −0.002 (2) | −0.002 (2) | 0.000 (2) |
C10 | 0.032 (3) | 0.023 (3) | 0.028 (3) | 0.004 (2) | 0.008 (2) | 0.004 (2) |
C11 | 0.031 (3) | 0.027 (3) | 0.022 (2) | −0.001 (2) | 0.000 (2) | 0.004 (2) |
C12 | 0.029 (3) | 0.014 (2) | 0.022 (2) | 0.003 (2) | 0.003 (2) | 0.0006 (19) |
O1 | 0.067 (4) | 0.026 (2) | 0.037 (2) | 0.013 (2) | 0.016 (2) | 0.006 (2) |
O2 | 0.038 (2) | 0.0217 (18) | 0.0248 (18) | −0.002 (2) | 0.002 (2) | 0.0037 (14) |
O3 | 0.038 (2) | 0.0247 (19) | 0.0236 (18) | −0.001 (2) | 0.001 (2) | −0.0071 (14) |
O4 | 0.037 (2) | 0.0177 (19) | 0.027 (2) | −0.0019 (17) | −0.0022 (18) | −0.0025 (16) |
O5 | 0.052 (3) | 0.020 (2) | 0.027 (2) | 0.000 (2) | 0.000 (2) | 0.0025 (17) |
O6 | 0.043 (3) | 0.0227 (19) | 0.0214 (17) | −0.002 (2) | −0.002 (2) | 0.0032 (14) |
O7 | 0.029 (2) | 0.021 (2) | 0.027 (2) | 0.0032 (16) | −0.0031 (17) | −0.0016 (17) |
O8 | 0.046 (3) | 0.0165 (19) | 0.033 (2) | 0.0039 (18) | −0.013 (2) | −0.0047 (16) |
S1S | 0.0401 (9) | 0.0298 (7) | 0.0289 (7) | −0.0069 (8) | −0.0017 (8) | 0.0033 (5) |
C1SA | 0.083 (9) | 0.098 (10) | 0.144 (12) | 0.052 (8) | −0.064 (8) | −0.085 (9) |
C1SB | 0.078 (8) | 0.070 (8) | 0.129 (11) | −0.045 (6) | 0.057 (7) | −0.056 (8) |
O1S | 0.048 (3) | 0.0250 (19) | 0.0251 (18) | −0.008 (2) | −0.001 (2) | 0.0046 (15) |
S2S | 0.0341 (8) | 0.0470 (9) | 0.0235 (6) | −0.0043 (8) | −0.0032 (7) | 0.0115 (6) |
C2SA | 0.034 (4) | 0.047 (4) | 0.040 (4) | −0.005 (3) | −0.007 (3) | 0.013 (4) |
C2SB | 0.031 (3) | 0.055 (5) | 0.030 (4) | −0.001 (3) | 0.001 (3) | 0.012 (3) |
O2S | 0.052 (3) | 0.040 (2) | 0.027 (2) | −0.003 (3) | −0.004 (2) | 0.0009 (17) |
S3S | 0.0304 (7) | 0.0186 (6) | 0.0267 (6) | −0.0023 (6) | 0.0001 (7) | −0.0035 (5) |
C3SA | 0.027 (3) | 0.029 (3) | 0.035 (3) | 0.001 (3) | 0.000 (3) | 0.001 (3) |
C3SB | 0.028 (3) | 0.023 (3) | 0.045 (4) | 0.001 (3) | −0.001 (3) | −0.006 (3) |
O3S | 0.042 (2) | 0.0189 (18) | 0.0265 (19) | 0.000 (2) | −0.004 (2) | −0.0004 (14) |
Geometric parameters (Å, º) top
N1—C1A | 1.356 (7) | O6—H6O | 0.8400 |
N1—C2 | 1.386 (7) | O8—H8O | 0.8400 |
N1—H1N | 0.96 (7) | S1S—O1S | 1.533 (4) |
C2—C3 | 1.375 (7) | S1S—C1SB | 1.746 (10) |
C2—C10 | 1.474 (8) | S1S—C1SA | 1.766 (11) |
C3—C3A | 1.425 (7) | C1SA—H1SA | 0.9800 |
C3—H3 | 0.9500 | C1SA—H1SB | 0.9800 |
C3A—C1A | 1.409 (7) | C1SA—H1SC | 0.9800 |
C3A—C4 | 1.449 (7) | C1SB—H1SD | 0.9800 |
C4—O3 | 1.217 (6) | C1SB—H1SE | 0.9800 |
C4—C5 | 1.563 (7) | C1SB—H1SF | 0.9800 |
C5—O4 | 1.207 (7) | S2S—O2S | 1.484 (5) |
C5—C5A | 1.515 (7) | S2S—C2SB | 1.775 (7) |
C5A—N6 | 1.342 (7) | S2S—C2SA | 1.780 (8) |
C5A—C9A | 1.415 (7) | C2SA—H2SA | 0.9800 |
N6—C7 | 1.343 (7) | C2SA—H2SB | 0.9800 |
C7—C8 | 1.401 (7) | C2SA—H2SC | 0.9800 |
C7—C11 | 1.516 (7) | C2SB—H2SD | 0.9800 |
C8—C9 | 1.391 (8) | C2SB—H2SE | 0.9800 |
C8—H8 | 0.9500 | C2SB—H2SF | 0.9800 |
C9—C9A | 1.424 (7) | S3S—O3S | 1.561 (4) |
C9—C12 | 1.525 (7) | S3S—C3SB | 1.762 (7) |
C9A—C1A | 1.455 (8) | S3S—C3SA | 1.780 (7) |
C10—O1 | 1.215 (8) | C3SA—H3SA | 0.9800 |
C10—O2 | 1.327 (7) | C3SA—H3SB | 0.9800 |
C11—O5 | 1.223 (7) | C3SA—H3SC | 0.9800 |
C11—O6 | 1.308 (7) | C3SB—H3SD | 0.9800 |
C12—O7 | 1.239 (7) | C3SB—H3SE | 0.9800 |
C12—O8 | 1.275 (7) | C3SB—H3SF | 0.9800 |
O2—H2O | 0.8400 | | |
| | | |
C1A—N1—C2 | 110.4 (5) | C11—O6—H6O | 109.5 |
C1A—N1—H1N | 122 (4) | C12—O8—H8O | 109.5 |
C2—N1—H1N | 127 (4) | O1S—S1S—C1SB | 105.5 (4) |
C3—C2—N1 | 108.5 (5) | O1S—S1S—C1SA | 106.3 (4) |
C3—C2—C10 | 133.4 (5) | C1SB—S1S—C1SA | 96.6 (7) |
N1—C2—C10 | 118.1 (5) | S1S—C1SA—H1SA | 109.5 |
C2—C3—C3A | 106.3 (4) | S1S—C1SA—H1SB | 109.5 |
C2—C3—H3 | 126.8 | H1SA—C1SA—H1SB | 109.5 |
C3A—C3—H3 | 126.8 | S1S—C1SA—H1SC | 109.5 |
C1A—C3A—C3 | 108.2 (4) | H1SA—C1SA—H1SC | 109.5 |
C1A—C3A—C4 | 122.5 (5) | H1SB—C1SA—H1SC | 109.5 |
C3—C3A—C4 | 129.2 (5) | S1S—C1SB—H1SD | 109.5 |
O3—C4—C3A | 126.1 (5) | S1S—C1SB—H1SE | 109.5 |
O3—C4—C5 | 119.4 (5) | H1SD—C1SB—H1SE | 109.5 |
C3A—C4—C5 | 114.5 (4) | S1S—C1SB—H1SF | 109.5 |
O4—C5—C5A | 122.5 (5) | H1SD—C1SB—H1SF | 109.5 |
O4—C5—C4 | 118.4 (5) | H1SE—C1SB—H1SF | 109.5 |
C5A—C5—C4 | 119.1 (4) | O2S—S2S—C2SB | 106.9 (4) |
N6—C5A—C9A | 125.1 (5) | O2S—S2S—C2SA | 106.9 (4) |
N6—C5A—C5 | 113.7 (5) | C2SB—S2S—C2SA | 96.4 (3) |
C9A—C5A—C5 | 121.2 (5) | S2S—C2SA—H2SA | 109.5 |
C5A—N6—C7 | 117.4 (5) | S2S—C2SA—H2SB | 109.5 |
N6—C7—C8 | 122.5 (5) | H2SA—C2SA—H2SB | 109.5 |
N6—C7—C11 | 117.5 (5) | S2S—C2SA—H2SC | 109.5 |
C8—C7—C11 | 120.0 (5) | H2SA—C2SA—H2SC | 109.5 |
C9—C8—C7 | 120.1 (5) | H2SB—C2SA—H2SC | 109.5 |
C9—C8—H8 | 119.9 | S2S—C2SB—H2SD | 109.5 |
C7—C8—H8 | 119.9 | S2S—C2SB—H2SE | 109.5 |
C8—C9—C9A | 118.5 (5) | H2SD—C2SB—H2SE | 109.5 |
C8—C9—C12 | 114.9 (5) | S2S—C2SB—H2SF | 109.5 |
C9A—C9—C12 | 126.6 (5) | H2SD—C2SB—H2SF | 109.5 |
C5A—C9A—C9 | 116.3 (5) | H2SE—C2SB—H2SF | 109.5 |
C5A—C9A—C1A | 117.2 (5) | O3S—S3S—C3SB | 103.3 (3) |
C9—C9A—C1A | 126.5 (5) | O3S—S3S—C3SA | 102.6 (3) |
N1—C1A—C3A | 106.5 (5) | C3SB—S3S—C3SA | 100.5 (3) |
N1—C1A—C9A | 128.8 (5) | S3S—C3SA—H3SA | 109.5 |
C3A—C1A—C9A | 124.5 (5) | S3S—C3SA—H3SB | 109.5 |
O1—C10—O2 | 125.6 (5) | H3SA—C3SA—H3SB | 109.5 |
O1—C10—C2 | 121.4 (5) | S3S—C3SA—H3SC | 109.5 |
O2—C10—C2 | 113.0 (5) | H3SA—C3SA—H3SC | 109.5 |
O5—C11—O6 | 125.1 (5) | H3SB—C3SA—H3SC | 109.5 |
O5—C11—C7 | 122.0 (5) | S3S—C3SB—H3SD | 109.5 |
O6—C11—C7 | 112.8 (5) | S3S—C3SB—H3SE | 109.5 |
O7—C12—O8 | 124.7 (5) | H3SD—C3SB—H3SE | 109.5 |
O7—C12—C9 | 121.5 (5) | S3S—C3SB—H3SF | 109.5 |
O8—C12—C9 | 113.7 (5) | H3SD—C3SB—H3SF | 109.5 |
C10—O2—H2O | 109.5 | H3SE—C3SB—H3SF | 109.5 |
| | | |
C1A—N1—C2—C3 | −0.3 (7) | N6—C5A—C9A—C1A | 178.4 (5) |
C1A—N1—C2—C10 | 178.9 (5) | C5—C5A—C9A—C1A | 1.1 (8) |
N1—C2—C3—C3A | 0.1 (7) | C8—C9—C9A—C5A | 1.8 (8) |
C10—C2—C3—C3A | −179.0 (6) | C12—C9—C9A—C5A | −177.2 (5) |
C2—C3—C3A—C1A | 0.1 (7) | C8—C9—C9A—C1A | −174.8 (5) |
C2—C3—C3A—C4 | 176.5 (6) | C12—C9—C9A—C1A | 6.2 (9) |
C1A—C3A—C4—O3 | −178.7 (6) | C2—N1—C1A—C3A | 0.4 (6) |
C3—C3A—C4—O3 | 5.3 (11) | C2—N1—C1A—C9A | 176.4 (5) |
C1A—C3A—C4—C5 | 2.6 (8) | C3—C3A—C1A—N1 | −0.3 (6) |
C3—C3A—C4—C5 | −173.3 (6) | C4—C3A—C1A—N1 | −177.0 (5) |
O3—C4—C5—O4 | −9.2 (9) | C3—C3A—C1A—C9A | −176.5 (5) |
C3A—C4—C5—O4 | 169.6 (5) | C4—C3A—C1A—C9A | 6.8 (9) |
O3—C4—C5—C5A | 171.7 (6) | C5A—C9A—C1A—N1 | 175.9 (5) |
C3A—C4—C5—C5A | −9.5 (8) | C9—C9A—C1A—N1 | −7.5 (9) |
O4—C5—C5A—N6 | 11.2 (8) | C5A—C9A—C1A—C3A | −8.8 (8) |
C4—C5—C5A—N6 | −169.7 (5) | C9—C9A—C1A—C3A | 167.9 (6) |
O4—C5—C5A—C9A | −171.2 (5) | C3—C2—C10—O1 | 175.0 (7) |
C4—C5—C5A—C9A | 7.8 (8) | N1—C2—C10—O1 | −4.1 (9) |
C9A—C5A—N6—C7 | −2.6 (8) | C3—C2—C10—O2 | −4.3 (10) |
C5—C5A—N6—C7 | 174.9 (5) | N1—C2—C10—O2 | 176.6 (5) |
C5A—N6—C7—C8 | 0.5 (8) | N6—C7—C11—O5 | −9.9 (9) |
C5A—N6—C7—C11 | −178.1 (5) | C8—C7—C11—O5 | 171.5 (6) |
N6—C7—C8—C9 | 2.7 (9) | N6—C7—C11—O6 | 171.5 (5) |
C11—C7—C8—C9 | −178.7 (5) | C8—C7—C11—O6 | −7.2 (8) |
C7—C8—C9—C9A | −3.7 (8) | C8—C9—C12—O7 | −143.3 (6) |
C7—C8—C9—C12 | 175.4 (5) | C9A—C9—C12—O7 | 35.7 (9) |
N6—C5A—C9A—C9 | 1.4 (8) | C8—C9—C12—O8 | 33.0 (7) |
C5—C5A—C9A—C9 | −175.9 (5) | C9A—C9—C12—O8 | −148.0 (6) |
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