Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054906/wn2215sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054906/wn2215Isup2.hkl |
CCDC reference: 672897
To a solution of 1-methylquinoline-2,4-dione (1 mmol) in dry toluene (20 ml), 2-[N-(3-methylbut-2-enyl)-N-tosylamino]butanal (1 mmol) and a catalytic amount of the base ethylenediamine-N,N'-diacetate (EDDA) were added and the reaction mixture was refluxed for 12 h. After completion of the reaction, the solvent was evaporated under reduced pressure and the crude product was chromatographed using a hexane-ethyl acetate (8:2 v/v) mixture to obtain the title compound. The compound was recrystallized from ethyl acetate solution by slow evaporation.
H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93–0.98 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl). A rotating group model was used for the methyl groups attached to aromatic rings. The displacement ellipsoid of methyl carbon atom C14B is unusually elongated and some of the Uij components have large values. Attempts to restrain the Uij components of C14B failed to improve the values. Hence the restraints were removed.
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
C26H30N2O4S | F(000) = 1984 |
Mr = 466.58 | Dx = 1.322 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 7777 reflections |
a = 24.7027 (7) Å | θ = 2.3–29.5° |
b = 10.2685 (3) Å | µ = 0.17 mm−1 |
c = 19.6195 (5) Å | T = 100 K |
β = 109.554 (1)° | Plate, colourless |
V = 4689.7 (2) Å3 | 0.29 × 0.20 × 0.10 mm |
Z = 8 |
Bruker SMART APEX2 CCD area-detector diffractometer | 13623 independent reflections |
Radiation source: fine-focus sealed tube | 9445 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
Detector resolution: 8.33 pixels mm-1 | θmax = 30.1°, θmin = 0.9° |
ω scans | h = −34→22 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −14→11 |
Tmin = 0.951, Tmax = 0.983 | l = −16→27 |
45928 measured reflections |
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)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.166 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0598P)2 + 5.1486P] where P = (Fo2 + 2Fc2)/3 |
13623 reflections | (Δ/σ)max = 0.001 |
599 parameters | Δρmax = 0.44 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
C26H30N2O4S | V = 4689.7 (2) Å3 |
Mr = 466.58 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 24.7027 (7) Å | µ = 0.17 mm−1 |
b = 10.2685 (3) Å | T = 100 K |
c = 19.6195 (5) Å | 0.29 × 0.20 × 0.10 mm |
β = 109.554 (1)° |
Bruker SMART APEX2 CCD area-detector diffractometer | 13623 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 9445 reflections with I > 2σ(I) |
Tmin = 0.951, Tmax = 0.983 | Rint = 0.055 |
45928 measured reflections |
R[F2 > 2σ(F2)] = 0.067 | 0 restraints |
wR(F2) = 0.166 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.44 e Å−3 |
13623 reflections | Δρmin = −0.47 e Å−3 |
599 parameters |
Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. |
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 | ||
S1A | 0.31763 (3) | 0.36357 (6) | 0.17299 (3) | 0.01999 (13) | |
O1A | 0.26114 (8) | 0.41782 (17) | 0.15589 (9) | 0.0269 (4) | |
O2A | 0.34738 (8) | 0.37166 (17) | 0.12168 (9) | 0.0283 (4) | |
O3A | 0.42201 (7) | 0.28125 (15) | 0.48549 (8) | 0.0180 (3) | |
O4A | 0.54792 (7) | 0.35142 (17) | 0.35169 (9) | 0.0230 (4) | |
N1A | 0.35808 (8) | 0.43454 (18) | 0.24673 (10) | 0.0170 (4) | |
N2A | 0.57206 (8) | 0.20597 (18) | 0.44420 (10) | 0.0166 (4) | |
C1A | 0.33462 (10) | 0.4457 (2) | 0.30734 (12) | 0.0175 (4) | |
H1A | 0.2960 | 0.4108 | 0.2939 | 0.021* | |
H1B | 0.3345 | 0.5354 | 0.3228 | 0.021* | |
C2A | 0.37659 (9) | 0.3639 (2) | 0.36535 (11) | 0.0143 (4) | |
H2A | 0.3694 | 0.2729 | 0.3501 | 0.017* | |
C3A | 0.43420 (9) | 0.4014 (2) | 0.35816 (11) | 0.0143 (4) | |
H3A | 0.4427 | 0.4916 | 0.3747 | 0.017* | |
C4A | 0.42151 (9) | 0.3987 (2) | 0.27559 (12) | 0.0176 (4) | |
H4A | 0.4263 | 0.3095 | 0.2608 | 0.021* | |
C5A | 0.37685 (9) | 0.3709 (2) | 0.44271 (12) | 0.0150 (4) | |
C6A | 0.46979 (9) | 0.2629 (2) | 0.46756 (12) | 0.0153 (4) | |
C7A | 0.47945 (9) | 0.3147 (2) | 0.40861 (12) | 0.0143 (4) | |
C8A | 0.31342 (10) | 0.1962 (2) | 0.19265 (12) | 0.0171 (4) | |
C9A | 0.35113 (10) | 0.1081 (2) | 0.17899 (13) | 0.0215 (5) | |
H9A | 0.3778 | 0.1358 | 0.1580 | 0.026* | |
C10A | 0.34866 (10) | −0.0227 (2) | 0.19714 (13) | 0.0219 (5) | |
H10A | 0.3739 | −0.0819 | 0.1880 | 0.026* | |
C11A | 0.30937 (10) | −0.0658 (2) | 0.22845 (13) | 0.0202 (5) | |
C12A | 0.27156 (10) | 0.0240 (2) | 0.24137 (13) | 0.0202 (5) | |
H12A | 0.2448 | −0.0037 | 0.2622 | 0.024* | |
C13A | 0.27346 (10) | 0.1543 (2) | 0.22350 (13) | 0.0211 (5) | |
H13A | 0.2480 | 0.2134 | 0.2322 | 0.025* | |
C14A | 0.30883 (11) | −0.2061 (2) | 0.25107 (15) | 0.0274 (5) | |
H14A | 0.3135 | −0.2620 | 0.2142 | 0.041* | |
H14B | 0.2729 | −0.2250 | 0.2578 | 0.041* | |
H14C | 0.3397 | −0.2207 | 0.2956 | 0.041* | |
C15A | 0.32242 (10) | 0.3164 (2) | 0.45037 (13) | 0.0202 (5) | |
H15A | 0.3149 | 0.2320 | 0.4282 | 0.030* | |
H15B | 0.2909 | 0.3736 | 0.4271 | 0.030* | |
H15C | 0.3268 | 0.3091 | 0.5007 | 0.030* | |
C16A | 0.39049 (11) | 0.5049 (2) | 0.47712 (13) | 0.0224 (5) | |
H16A | 0.3898 | 0.5014 | 0.5257 | 0.034* | |
H16B | 0.3623 | 0.5663 | 0.4496 | 0.034* | |
H16C | 0.4279 | 0.5315 | 0.4778 | 0.034* | |
C17A | 0.51136 (9) | 0.1791 (2) | 0.51761 (12) | 0.0156 (4) | |
C18A | 0.50194 (10) | 0.1239 (2) | 0.57826 (12) | 0.0187 (4) | |
H18A | 0.4682 | 0.1423 | 0.5875 | 0.022* | |
C19A | 0.54223 (11) | 0.0429 (2) | 0.62398 (13) | 0.0218 (5) | |
H19A | 0.5359 | 0.0070 | 0.6642 | 0.026* | |
C20A | 0.59258 (10) | 0.0149 (2) | 0.60966 (13) | 0.0216 (5) | |
H20A | 0.6195 | −0.0407 | 0.6404 | 0.026* | |
C21A | 0.60328 (10) | 0.0677 (2) | 0.55114 (13) | 0.0194 (5) | |
H21A | 0.6373 | 0.0486 | 0.5428 | 0.023* | |
C22A | 0.56250 (9) | 0.1510 (2) | 0.50379 (12) | 0.0165 (4) | |
C23A | 0.53431 (9) | 0.2938 (2) | 0.39858 (12) | 0.0163 (4) | |
C24A | 0.62589 (10) | 0.1806 (3) | 0.43081 (14) | 0.0248 (5) | |
H24A | 0.6329 | 0.0885 | 0.4326 | 0.037* | |
H24B | 0.6569 | 0.2233 | 0.4671 | 0.037* | |
H24C | 0.6232 | 0.2133 | 0.3839 | 0.037* | |
C25A | 0.45550 (11) | 0.4913 (3) | 0.24427 (14) | 0.0261 (5) | |
H25A | 0.4921 | 0.4510 | 0.2489 | 0.031* | |
H25B | 0.4347 | 0.5024 | 0.1931 | 0.031* | |
C26A | 0.46692 (14) | 0.6248 (3) | 0.27936 (17) | 0.0380 (7) | |
H26A | 0.4884 | 0.6763 | 0.2565 | 0.057* | |
H26B | 0.4885 | 0.6155 | 0.3299 | 0.057* | |
H26C | 0.4310 | 0.6670 | 0.2740 | 0.057* | |
S1B | 0.17892 (3) | 0.62891 (6) | 0.32745 (4) | 0.02446 (14) | |
O1B | 0.23600 (8) | 0.57809 (18) | 0.35872 (11) | 0.0349 (5) | |
O2B | 0.14798 (9) | 0.6121 (2) | 0.25207 (10) | 0.0363 (5) | |
O3B | 0.07962 (7) | 0.72509 (16) | 0.55757 (9) | 0.0224 (4) | |
O4B | −0.04453 (8) | 0.6673 (2) | 0.31508 (10) | 0.0323 (4) | |
N1B | 0.14028 (9) | 0.56320 (19) | 0.37157 (11) | 0.0211 (4) | |
N2B | −0.07210 (8) | 0.79519 (19) | 0.39207 (11) | 0.0211 (4) | |
C1B | 0.16564 (11) | 0.5594 (2) | 0.45133 (14) | 0.0239 (5) | |
H1C | 0.2040 | 0.5964 | 0.4679 | 0.029* | |
H1D | 0.1672 | 0.4711 | 0.4695 | 0.029* | |
C2B | 0.12392 (10) | 0.6426 (2) | 0.47433 (13) | 0.0192 (5) | |
H2B | 0.1302 | 0.7332 | 0.4630 | 0.023* | |
C3B | 0.06602 (10) | 0.6014 (2) | 0.42108 (12) | 0.0184 (4) | |
H3B | 0.0583 | 0.5123 | 0.4332 | 0.022* | |
C4B | 0.07693 (10) | 0.5972 (2) | 0.34795 (13) | 0.0214 (5) | |
H4B | 0.0713 | 0.6847 | 0.3267 | 0.026* | |
C5B | 0.12589 (10) | 0.6398 (2) | 0.55229 (13) | 0.0204 (5) | |
C6B | 0.03148 (10) | 0.7423 (2) | 0.49971 (13) | 0.0181 (4) | |
C7B | 0.02111 (10) | 0.6893 (2) | 0.43303 (13) | 0.0190 (5) | |
C8B | 0.18260 (10) | 0.7985 (2) | 0.34440 (14) | 0.0238 (5) | |
C9B | 0.14173 (11) | 0.8800 (3) | 0.29762 (16) | 0.0291 (6) | |
H9B | 0.1139 | 0.8465 | 0.2567 | 0.035* | |
C10B | 0.14328 (12) | 1.0119 (3) | 0.3131 (2) | 0.0408 (8) | |
H10B | 0.1163 | 1.0668 | 0.2819 | 0.049* | |
C11B | 0.18375 (13) | 1.0639 (3) | 0.3735 (2) | 0.0462 (9) | |
C12B | 0.22467 (12) | 0.9812 (3) | 0.4189 (2) | 0.0444 (8) | |
H12B | 0.2526 | 1.0150 | 0.4596 | 0.053* | |
C13B | 0.22450 (11) | 0.8488 (3) | 0.40430 (16) | 0.0304 (6) | |
H13B | 0.2524 | 0.7946 | 0.4346 | 0.037* | |
C14B | 0.18209 (16) | 1.2055 (3) | 0.3921 (3) | 0.0892 (18) | |
H14D | 0.1448 | 1.2266 | 0.3943 | 0.134* | |
H14E | 0.1896 | 1.2579 | 0.3557 | 0.134* | |
H14F | 0.2108 | 1.2226 | 0.4382 | 0.134* | |
C15B | 0.18005 (11) | 0.7030 (3) | 0.60244 (14) | 0.0286 (6) | |
H15D | 0.1850 | 0.7869 | 0.5837 | 0.043* | |
H15E | 0.2126 | 0.6490 | 0.6057 | 0.043* | |
H15F | 0.1769 | 0.7130 | 0.6496 | 0.043* | |
C16B | 0.11612 (12) | 0.5061 (3) | 0.57967 (14) | 0.0293 (6) | |
H16D | 0.0816 | 0.4687 | 0.5468 | 0.044* | |
H16E | 0.1125 | 0.5146 | 0.6267 | 0.044* | |
H16F | 0.1481 | 0.4506 | 0.5828 | 0.044* | |
C17B | −0.00982 (10) | 0.8270 (2) | 0.51506 (13) | 0.0199 (5) | |
C18B | 0.00104 (11) | 0.8865 (2) | 0.58266 (14) | 0.0222 (5) | |
H18B | 0.0358 | 0.8714 | 0.6194 | 0.027* | |
C19B | −0.03907 (11) | 0.9669 (2) | 0.59513 (14) | 0.0251 (5) | |
H19B | −0.0316 | 1.0065 | 0.6400 | 0.030* | |
C20B | −0.09128 (11) | 0.9886 (2) | 0.53973 (15) | 0.0278 (6) | |
H20B | −0.1185 | 1.0426 | 0.5483 | 0.033* | |
C21B | −0.10314 (10) | 0.9319 (2) | 0.47305 (14) | 0.0240 (5) | |
H21B | −0.1382 | 0.9469 | 0.4370 | 0.029* | |
C22B | −0.06195 (10) | 0.8508 (2) | 0.45956 (13) | 0.0205 (5) | |
C23B | −0.03295 (10) | 0.7149 (2) | 0.37602 (13) | 0.0211 (5) | |
C24B | −0.12697 (11) | 0.8197 (3) | 0.33482 (15) | 0.0321 (6) | |
H24D | −0.1287 | 0.7704 | 0.2926 | 0.048* | |
H24E | −0.1303 | 0.9109 | 0.3232 | 0.048* | |
H24F | −0.1579 | 0.7941 | 0.3512 | 0.048* | |
C25B | 0.04245 (11) | 0.4992 (3) | 0.29093 (14) | 0.0279 (6) | |
H25C | 0.0067 | 0.5402 | 0.2621 | 0.034* | |
H25D | 0.0640 | 0.4801 | 0.2589 | 0.034* | |
C26B | 0.02830 (14) | 0.3718 (3) | 0.32003 (18) | 0.0409 (7) | |
H26D | 0.0633 | 0.3285 | 0.3474 | 0.061* | |
H26E | 0.0068 | 0.3173 | 0.2804 | 0.061* | |
H26F | 0.0059 | 0.3888 | 0.3507 | 0.061* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0234 (3) | 0.0189 (3) | 0.0154 (3) | 0.0000 (2) | 0.0035 (2) | 0.0017 (2) |
O1A | 0.0248 (9) | 0.0242 (9) | 0.0241 (10) | 0.0042 (7) | −0.0022 (7) | 0.0033 (7) |
O2A | 0.0388 (11) | 0.0285 (9) | 0.0190 (9) | −0.0065 (8) | 0.0114 (8) | 0.0000 (7) |
O3A | 0.0152 (8) | 0.0215 (8) | 0.0178 (8) | 0.0034 (6) | 0.0063 (6) | 0.0045 (6) |
O4A | 0.0196 (8) | 0.0301 (9) | 0.0212 (9) | 0.0017 (7) | 0.0095 (7) | 0.0018 (7) |
N1A | 0.0174 (9) | 0.0177 (9) | 0.0150 (9) | 0.0015 (7) | 0.0041 (8) | 0.0006 (7) |
N2A | 0.0147 (9) | 0.0170 (9) | 0.0178 (10) | 0.0000 (7) | 0.0051 (8) | −0.0035 (7) |
C1A | 0.0175 (11) | 0.0183 (10) | 0.0165 (11) | 0.0013 (8) | 0.0054 (9) | −0.0008 (8) |
C2A | 0.0161 (10) | 0.0128 (9) | 0.0146 (10) | −0.0004 (8) | 0.0059 (8) | −0.0002 (8) |
C3A | 0.0163 (10) | 0.0135 (9) | 0.0132 (10) | −0.0008 (8) | 0.0050 (8) | −0.0003 (8) |
C4A | 0.0170 (11) | 0.0193 (10) | 0.0159 (11) | 0.0050 (8) | 0.0046 (9) | 0.0026 (8) |
C5A | 0.0141 (10) | 0.0155 (10) | 0.0151 (10) | 0.0032 (8) | 0.0046 (8) | 0.0011 (8) |
C6A | 0.0146 (10) | 0.0153 (10) | 0.0145 (11) | −0.0006 (8) | 0.0029 (8) | −0.0040 (8) |
C7A | 0.0144 (10) | 0.0137 (10) | 0.0137 (10) | −0.0010 (8) | 0.0030 (8) | −0.0024 (8) |
C8A | 0.0199 (11) | 0.0161 (10) | 0.0129 (10) | −0.0026 (8) | 0.0021 (9) | −0.0025 (8) |
C9A | 0.0211 (12) | 0.0254 (12) | 0.0188 (12) | −0.0034 (9) | 0.0079 (10) | −0.0052 (9) |
C10A | 0.0186 (11) | 0.0210 (11) | 0.0254 (13) | 0.0016 (9) | 0.0063 (10) | −0.0041 (9) |
C11A | 0.0176 (11) | 0.0198 (11) | 0.0179 (11) | −0.0022 (9) | −0.0008 (9) | −0.0022 (9) |
C12A | 0.0155 (11) | 0.0233 (11) | 0.0202 (12) | −0.0034 (9) | 0.0040 (9) | 0.0006 (9) |
C13A | 0.0143 (11) | 0.0240 (12) | 0.0229 (12) | 0.0014 (9) | 0.0035 (9) | −0.0020 (9) |
C14A | 0.0243 (13) | 0.0224 (12) | 0.0302 (14) | −0.0011 (10) | 0.0021 (11) | 0.0046 (10) |
C15A | 0.0191 (11) | 0.0206 (11) | 0.0223 (12) | 0.0001 (9) | 0.0086 (10) | 0.0023 (9) |
C16A | 0.0277 (13) | 0.0223 (11) | 0.0193 (12) | −0.0008 (10) | 0.0108 (10) | −0.0061 (9) |
C17A | 0.0161 (11) | 0.0141 (10) | 0.0146 (11) | −0.0011 (8) | 0.0026 (9) | −0.0038 (8) |
C18A | 0.0203 (11) | 0.0176 (11) | 0.0171 (11) | −0.0016 (9) | 0.0048 (9) | −0.0013 (8) |
C19A | 0.0259 (12) | 0.0197 (11) | 0.0155 (11) | 0.0001 (9) | 0.0010 (10) | 0.0015 (9) |
C20A | 0.0219 (12) | 0.0162 (10) | 0.0193 (12) | 0.0026 (9) | −0.0030 (9) | −0.0003 (9) |
C21A | 0.0167 (11) | 0.0168 (11) | 0.0213 (12) | 0.0005 (8) | 0.0018 (9) | −0.0039 (9) |
C22A | 0.0161 (10) | 0.0137 (10) | 0.0176 (11) | −0.0012 (8) | 0.0028 (9) | −0.0037 (8) |
C23A | 0.0144 (10) | 0.0174 (10) | 0.0153 (11) | −0.0002 (8) | 0.0028 (9) | −0.0033 (8) |
C24A | 0.0189 (12) | 0.0300 (13) | 0.0271 (13) | 0.0034 (10) | 0.0097 (10) | −0.0033 (10) |
C25A | 0.0213 (12) | 0.0353 (14) | 0.0226 (13) | 0.0045 (10) | 0.0086 (10) | 0.0115 (10) |
C26A | 0.0419 (17) | 0.0297 (15) | 0.0414 (18) | −0.0121 (12) | 0.0127 (14) | 0.0107 (12) |
S1B | 0.0275 (3) | 0.0224 (3) | 0.0290 (3) | 0.0038 (2) | 0.0167 (3) | 0.0031 (2) |
O1B | 0.0319 (10) | 0.0307 (10) | 0.0520 (13) | 0.0133 (8) | 0.0271 (10) | 0.0111 (9) |
O2B | 0.0489 (13) | 0.0402 (11) | 0.0259 (10) | −0.0057 (9) | 0.0207 (10) | −0.0033 (8) |
O3B | 0.0195 (8) | 0.0271 (9) | 0.0193 (9) | 0.0065 (7) | 0.0049 (7) | 0.0003 (7) |
O4B | 0.0283 (10) | 0.0481 (12) | 0.0171 (9) | 0.0069 (9) | 0.0033 (8) | −0.0012 (8) |
N1B | 0.0234 (10) | 0.0199 (10) | 0.0229 (11) | 0.0058 (8) | 0.0115 (9) | 0.0054 (8) |
N2B | 0.0148 (9) | 0.0218 (10) | 0.0241 (11) | 0.0024 (8) | 0.0031 (8) | 0.0042 (8) |
C1B | 0.0219 (12) | 0.0231 (12) | 0.0277 (13) | 0.0068 (9) | 0.0099 (10) | 0.0048 (10) |
C2B | 0.0173 (11) | 0.0175 (10) | 0.0224 (12) | 0.0028 (8) | 0.0060 (9) | 0.0048 (9) |
C3B | 0.0187 (11) | 0.0175 (10) | 0.0191 (11) | 0.0021 (8) | 0.0066 (9) | 0.0034 (9) |
C4B | 0.0243 (12) | 0.0216 (11) | 0.0204 (12) | 0.0042 (9) | 0.0102 (10) | 0.0034 (9) |
C5B | 0.0193 (11) | 0.0209 (11) | 0.0203 (12) | 0.0062 (9) | 0.0059 (9) | 0.0047 (9) |
C6B | 0.0163 (11) | 0.0172 (10) | 0.0200 (12) | 0.0002 (8) | 0.0050 (9) | 0.0027 (8) |
C7B | 0.0182 (11) | 0.0180 (11) | 0.0221 (12) | 0.0005 (8) | 0.0087 (9) | 0.0043 (9) |
C8B | 0.0200 (12) | 0.0222 (12) | 0.0329 (14) | 0.0019 (9) | 0.0138 (11) | 0.0041 (10) |
C9B | 0.0212 (12) | 0.0311 (14) | 0.0384 (15) | 0.0043 (10) | 0.0146 (11) | 0.0150 (11) |
C10B | 0.0237 (14) | 0.0284 (14) | 0.079 (2) | 0.0085 (11) | 0.0289 (15) | 0.0227 (15) |
C11B | 0.0258 (15) | 0.0222 (14) | 0.102 (3) | −0.0040 (11) | 0.0373 (18) | −0.0020 (15) |
C12B | 0.0214 (14) | 0.0398 (17) | 0.074 (2) | −0.0098 (12) | 0.0193 (15) | −0.0147 (16) |
C13B | 0.0176 (12) | 0.0326 (14) | 0.0392 (16) | 0.0010 (10) | 0.0071 (11) | −0.0006 (12) |
C14B | 0.041 (2) | 0.0249 (17) | 0.218 (6) | −0.0077 (15) | 0.064 (3) | −0.025 (2) |
C15B | 0.0220 (13) | 0.0376 (15) | 0.0214 (13) | 0.0053 (11) | 0.0010 (10) | 0.0010 (11) |
C16B | 0.0378 (15) | 0.0286 (13) | 0.0240 (13) | 0.0048 (11) | 0.0136 (12) | 0.0111 (10) |
C17B | 0.0200 (12) | 0.0178 (11) | 0.0232 (12) | −0.0005 (9) | 0.0092 (10) | 0.0023 (9) |
C18B | 0.0225 (12) | 0.0198 (11) | 0.0267 (13) | 0.0001 (9) | 0.0117 (10) | 0.0043 (9) |
C19B | 0.0298 (13) | 0.0223 (12) | 0.0280 (14) | 0.0015 (10) | 0.0158 (11) | 0.0006 (10) |
C20B | 0.0271 (13) | 0.0206 (12) | 0.0408 (16) | 0.0043 (10) | 0.0183 (12) | 0.0029 (11) |
C21B | 0.0183 (11) | 0.0223 (12) | 0.0329 (14) | 0.0028 (9) | 0.0103 (10) | 0.0063 (10) |
C22B | 0.0190 (11) | 0.0175 (11) | 0.0264 (13) | −0.0010 (9) | 0.0094 (10) | 0.0039 (9) |
C23B | 0.0199 (12) | 0.0220 (11) | 0.0219 (12) | 0.0019 (9) | 0.0079 (10) | 0.0053 (9) |
C24B | 0.0230 (13) | 0.0360 (15) | 0.0311 (15) | 0.0058 (11) | 0.0010 (11) | 0.0049 (12) |
C25B | 0.0289 (14) | 0.0314 (14) | 0.0238 (13) | 0.0035 (11) | 0.0093 (11) | −0.0031 (10) |
C26B | 0.0443 (18) | 0.0349 (16) | 0.0421 (18) | −0.0119 (13) | 0.0127 (15) | −0.0107 (13) |
S1A—O2A | 1.4337 (18) | S1B—O2B | 1.430 (2) |
S1A—O1A | 1.4342 (18) | S1B—O1B | 1.4345 (19) |
S1A—N1A | 1.629 (2) | S1B—N1B | 1.634 (2) |
S1A—C8A | 1.772 (2) | S1B—C8B | 1.770 (3) |
O3A—C6A | 1.353 (3) | O3B—C6B | 1.353 (3) |
O3A—C5A | 1.473 (3) | O3B—C5B | 1.471 (3) |
O4A—C23A | 1.231 (3) | O4B—C23B | 1.233 (3) |
N1A—C1A | 1.491 (3) | N1B—C1B | 1.479 (3) |
N1A—C4A | 1.522 (3) | N1B—C4B | 1.517 (3) |
N2A—C23A | 1.388 (3) | N2B—C23B | 1.385 (3) |
N2A—C22A | 1.388 (3) | N2B—C22B | 1.386 (3) |
N2A—C24A | 1.462 (3) | N2B—C24B | 1.464 (3) |
C1A—C2A | 1.512 (3) | C1B—C2B | 1.519 (3) |
C1A—H1A | 0.97 | C1B—H1C | 0.97 |
C1A—H1B | 0.97 | C1B—H1D | 0.97 |
C2A—C5A | 1.517 (3) | C2B—C5B | 1.514 (3) |
C2A—C3A | 1.525 (3) | C2B—C3B | 1.522 (3) |
C2A—H2A | 0.98 | C2B—H2B | 0.98 |
C3A—C7A | 1.510 (3) | C3B—C7B | 1.509 (3) |
C3A—C4A | 1.544 (3) | C3B—C4B | 1.546 (3) |
C3A—H3A | 0.98 | C3B—H3B | 0.98 |
C4A—C25A | 1.527 (3) | C4B—C25B | 1.533 (4) |
C4A—H4A | 0.98 | C4B—H4B | 0.98 |
C5A—C15A | 1.510 (3) | C5B—C15B | 1.516 (4) |
C5A—C16A | 1.519 (3) | C5B—C16B | 1.523 (3) |
C6A—C7A | 1.365 (3) | C6B—C7B | 1.360 (3) |
C6A—C17A | 1.444 (3) | C6B—C17B | 1.446 (3) |
C7A—C23A | 1.449 (3) | C7B—C23B | 1.450 (3) |
C8A—C9A | 1.388 (3) | C8B—C13B | 1.380 (4) |
C8A—C13A | 1.388 (3) | C8B—C9B | 1.394 (3) |
C9A—C10A | 1.396 (3) | C9B—C10B | 1.386 (4) |
C9A—H9A | 0.93 | C9B—H9B | 0.93 |
C10A—C11A | 1.384 (3) | C10B—C11B | 1.377 (5) |
C10A—H10A | 0.93 | C10B—H10B | 0.93 |
C11A—C12A | 1.395 (3) | C11B—C12B | 1.390 (5) |
C11A—C14A | 1.509 (3) | C11B—C14B | 1.504 (4) |
C12A—C13A | 1.388 (3) | C12B—C13B | 1.389 (4) |
C12A—H12A | 0.93 | C12B—H12B | 0.93 |
C13A—H13A | 0.93 | C13B—H13B | 0.93 |
C14A—H14A | 0.96 | C14B—H14D | 0.96 |
C14A—H14B | 0.96 | C14B—H14E | 0.96 |
C14A—H14C | 0.96 | C14B—H14F | 0.96 |
C15A—H15A | 0.96 | C15B—H15D | 0.96 |
C15A—H15B | 0.96 | C15B—H15E | 0.96 |
C15A—H15C | 0.96 | C15B—H15F | 0.96 |
C16A—H16A | 0.96 | C16B—H16D | 0.96 |
C16A—H16B | 0.96 | C16B—H16E | 0.96 |
C16A—H16C | 0.96 | C16B—H16F | 0.96 |
C17A—C18A | 1.406 (3) | C17B—C22B | 1.402 (3) |
C17A—C22A | 1.408 (3) | C17B—C18B | 1.402 (3) |
C18A—C19A | 1.374 (3) | C18B—C19B | 1.373 (3) |
C18A—H18A | 0.93 | C18B—H18B | 0.93 |
C19A—C20A | 1.394 (3) | C19B—C20B | 1.399 (4) |
C19A—H19A | 0.93 | C19B—H19B | 0.93 |
C20A—C21A | 1.373 (3) | C20B—C21B | 1.371 (4) |
C20A—H20A | 0.93 | C20B—H20B | 0.93 |
C21A—C22A | 1.408 (3) | C21B—C22B | 1.407 (3) |
C21A—H21A | 0.93 | C21B—H21B | 0.93 |
C24A—H24A | 0.96 | C24B—H24D | 0.96 |
C24A—H24B | 0.96 | C24B—H24E | 0.96 |
C24A—H24C | 0.96 | C24B—H24F | 0.96 |
C25A—C26A | 1.517 (4) | C25B—C26B | 1.515 (4) |
C25A—H25A | 0.97 | C25B—H25C | 0.97 |
C25A—H25B | 0.97 | C25B—H25D | 0.97 |
C26A—H26A | 0.96 | C26B—H26D | 0.96 |
C26A—H26B | 0.96 | C26B—H26E | 0.96 |
C26A—H26C | 0.96 | C26B—H26F | 0.96 |
O2A—S1A—O1A | 120.04 (11) | O2B—S1B—O1B | 120.47 (12) |
O2A—S1A—N1A | 106.95 (10) | O2B—S1B—N1B | 107.05 (11) |
O1A—S1A—N1A | 107.06 (10) | O1B—S1B—N1B | 106.75 (11) |
O2A—S1A—C8A | 106.88 (11) | O2B—S1B—C8B | 106.82 (12) |
O1A—S1A—C8A | 107.71 (11) | O1B—S1B—C8B | 107.23 (12) |
N1A—S1A—C8A | 107.68 (10) | N1B—S1B—C8B | 108.02 (11) |
C6A—O3A—C5A | 119.92 (16) | C6B—O3B—C5B | 120.29 (18) |
C1A—N1A—C4A | 110.37 (17) | C1B—N1B—C4B | 110.95 (17) |
C1A—N1A—S1A | 117.12 (15) | C1B—N1B—S1B | 117.12 (16) |
C4A—N1A—S1A | 118.12 (14) | C4B—N1B—S1B | 117.97 (15) |
C23A—N2A—C22A | 122.72 (18) | C23B—N2B—C22B | 123.1 (2) |
C23A—N2A—C24A | 117.08 (19) | C23B—N2B—C24B | 117.8 (2) |
C22A—N2A—C24A | 120.00 (19) | C22B—N2B—C24B | 119.2 (2) |
N1A—C1A—C2A | 101.89 (17) | N1B—C1B—C2B | 102.15 (18) |
N1A—C1A—H1A | 111.4 | N1B—C1B—H1C | 111.3 |
C2A—C1A—H1A | 111.4 | C2B—C1B—H1C | 111.3 |
N1A—C1A—H1B | 111.4 | N1B—C1B—H1D | 111.3 |
C2A—C1A—H1B | 111.4 | C2B—C1B—H1D | 111.3 |
H1A—C1A—H1B | 109.3 | H1C—C1B—H1D | 109.2 |
C1A—C2A—C5A | 119.93 (18) | C5B—C2B—C1B | 119.59 (19) |
C1A—C2A—C3A | 102.50 (17) | C5B—C2B—C3B | 113.15 (19) |
C5A—C2A—C3A | 112.88 (18) | C1B—C2B—C3B | 102.40 (19) |
C1A—C2A—H2A | 106.9 | C5B—C2B—H2B | 107.0 |
C5A—C2A—H2A | 106.9 | C1B—C2B—H2B | 107.0 |
C3A—C2A—H2A | 106.9 | C3B—C2B—H2B | 107.0 |
C7A—C3A—C2A | 107.43 (17) | C7B—C3B—C2B | 107.33 (19) |
C7A—C3A—C4A | 121.54 (18) | C7B—C3B—C4B | 121.75 (19) |
C2A—C3A—C4A | 102.96 (17) | C2B—C3B—C4B | 103.24 (18) |
C7A—C3A—H3A | 108.1 | C7B—C3B—H3B | 107.9 |
C2A—C3A—H3A | 108.1 | C2B—C3B—H3B | 107.9 |
C4A—C3A—H3A | 108.1 | C4B—C3B—H3B | 107.9 |
N1A—C4A—C25A | 109.64 (18) | N1B—C4B—C25B | 109.63 (19) |
N1A—C4A—C3A | 102.03 (16) | N1B—C4B—C3B | 101.85 (18) |
C25A—C4A—C3A | 117.7 (2) | C25B—C4B—C3B | 117.9 (2) |
N1A—C4A—H4A | 109.0 | N1B—C4B—H4B | 109.0 |
C25A—C4A—H4A | 109.0 | C25B—C4B—H4B | 109.0 |
C3A—C4A—H4A | 109.0 | C3B—C4B—H4B | 109.0 |
O3A—C5A—C15A | 103.96 (17) | O3B—C5B—C2B | 107.27 (18) |
O3A—C5A—C2A | 106.81 (16) | O3B—C5B—C15B | 103.73 (19) |
C15A—C5A—C2A | 112.11 (19) | C2B—C5B—C15B | 111.7 (2) |
O3A—C5A—C16A | 107.43 (18) | O3B—C5B—C16B | 107.07 (19) |
C15A—C5A—C16A | 111.33 (18) | C2B—C5B—C16B | 114.7 (2) |
C2A—C5A—C16A | 114.43 (18) | C15B—C5B—C16B | 111.5 (2) |
O3A—C6A—C7A | 125.6 (2) | O3B—C6B—C7B | 125.8 (2) |
O3A—C6A—C17A | 112.93 (18) | O3B—C6B—C17B | 112.8 (2) |
C7A—C6A—C17A | 121.5 (2) | C7B—C6B—C17B | 121.5 (2) |
C6A—C7A—C23A | 119.6 (2) | C6B—C7B—C23B | 119.9 (2) |
C6A—C7A—C3A | 118.96 (19) | C6B—C7B—C3B | 118.5 (2) |
C23A—C7A—C3A | 121.27 (19) | C23B—C7B—C3B | 121.6 (2) |
C9A—C8A—C13A | 120.2 (2) | C13B—C8B—C9B | 120.5 (2) |
C9A—C8A—S1A | 119.90 (17) | C13B—C8B—S1B | 120.3 (2) |
C13A—C8A—S1A | 119.86 (17) | C9B—C8B—S1B | 119.1 (2) |
C8A—C9A—C10A | 119.3 (2) | C10B—C9B—C8B | 118.8 (3) |
C8A—C9A—H9A | 120.4 | C10B—C9B—H9B | 120.6 |
C10A—C9A—H9A | 120.4 | C8B—C9B—H9B | 120.6 |
C11A—C10A—C9A | 121.2 (2) | C11B—C10B—C9B | 121.8 (3) |
C11A—C10A—H10A | 119.4 | C11B—C10B—H10B | 119.1 |
C9A—C10A—H10A | 119.4 | C9B—C10B—H10B | 119.1 |
C10A—C11A—C12A | 118.7 (2) | C10B—C11B—C12B | 118.5 (3) |
C10A—C11A—C14A | 120.9 (2) | C10B—C11B—C14B | 120.9 (3) |
C12A—C11A—C14A | 120.4 (2) | C12B—C11B—C14B | 120.6 (4) |
C13A—C12A—C11A | 120.7 (2) | C13B—C12B—C11B | 121.0 (3) |
C13A—C12A—H12A | 119.7 | C13B—C12B—H12B | 119.5 |
C11A—C12A—H12A | 119.7 | C11B—C12B—H12B | 119.5 |
C8A—C13A—C12A | 119.9 (2) | C8B—C13B—C12B | 119.4 (3) |
C8A—C13A—H13A | 120.1 | C8B—C13B—H13B | 120.3 |
C12A—C13A—H13A | 120.1 | C12B—C13B—H13B | 120.3 |
C11A—C14A—H14A | 109.5 | C11B—C14B—H14D | 109.5 |
C11A—C14A—H14B | 109.5 | C11B—C14B—H14E | 109.5 |
H14A—C14A—H14B | 109.5 | H14D—C14B—H14E | 109.5 |
C11A—C14A—H14C | 109.5 | C11B—C14B—H14F | 109.5 |
H14A—C14A—H14C | 109.5 | H14D—C14B—H14F | 109.5 |
H14B—C14A—H14C | 109.5 | H14E—C14B—H14F | 109.5 |
C5A—C15A—H15A | 109.5 | C5B—C15B—H15D | 109.5 |
C5A—C15A—H15B | 109.5 | C5B—C15B—H15E | 109.5 |
H15A—C15A—H15B | 109.5 | H15D—C15B—H15E | 109.5 |
C5A—C15A—H15C | 109.5 | C5B—C15B—H15F | 109.5 |
H15A—C15A—H15C | 109.5 | H15D—C15B—H15F | 109.5 |
H15B—C15A—H15C | 109.5 | H15E—C15B—H15F | 109.5 |
C5A—C16A—H16A | 109.5 | C5B—C16B—H16D | 109.5 |
C5A—C16A—H16B | 109.5 | C5B—C16B—H16E | 109.5 |
H16A—C16A—H16B | 109.5 | H16D—C16B—H16E | 109.5 |
C5A—C16A—H16C | 109.5 | C5B—C16B—H16F | 109.5 |
H16A—C16A—H16C | 109.5 | H16D—C16B—H16F | 109.5 |
H16B—C16A—H16C | 109.5 | H16E—C16B—H16F | 109.5 |
C18A—C17A—C22A | 119.6 (2) | C22B—C17B—C18B | 119.6 (2) |
C18A—C17A—C6A | 122.3 (2) | C22B—C17B—C6B | 118.2 (2) |
C22A—C17A—C6A | 118.1 (2) | C18B—C17B—C6B | 122.3 (2) |
C19A—C18A—C17A | 120.5 (2) | C19B—C18B—C17B | 120.6 (2) |
C19A—C18A—H18A | 119.8 | C19B—C18B—H18B | 119.7 |
C17A—C18A—H18A | 119.8 | C17B—C18B—H18B | 119.7 |
C18A—C19A—C20A | 119.6 (2) | C18B—C19B—C20B | 119.3 (2) |
C18A—C19A—H19A | 120.2 | C18B—C19B—H19B | 120.3 |
C20A—C19A—H19A | 120.2 | C20B—C19B—H19B | 120.3 |
C21A—C20A—C19A | 121.4 (2) | C21B—C20B—C19B | 121.4 (2) |
C21A—C20A—H20A | 119.3 | C21B—C20B—H20B | 119.3 |
C19A—C20A—H20A | 119.3 | C19B—C20B—H20B | 119.3 |
C20A—C21A—C22A | 119.7 (2) | C20B—C21B—C22B | 119.6 (2) |
C20A—C21A—H21A | 120.1 | C20B—C21B—H21B | 120.2 |
C22A—C21A—H21A | 120.1 | C22B—C21B—H21B | 120.2 |
N2A—C22A—C17A | 119.7 (2) | N2B—C22B—C17B | 119.7 (2) |
N2A—C22A—C21A | 121.1 (2) | N2B—C22B—C21B | 120.8 (2) |
C17A—C22A—C21A | 119.2 (2) | C17B—C22B—C21B | 119.4 (2) |
O4A—C23A—N2A | 120.1 (2) | O4B—C23B—N2B | 120.2 (2) |
O4A—C23A—C7A | 122.1 (2) | O4B—C23B—C7B | 122.1 (2) |
N2A—C23A—C7A | 117.77 (19) | N2B—C23B—C7B | 117.7 (2) |
N2A—C24A—H24A | 109.5 | N2B—C24B—H24D | 109.5 |
N2A—C24A—H24B | 109.5 | N2B—C24B—H24E | 109.5 |
H24A—C24A—H24B | 109.5 | H24D—C24B—H24E | 109.5 |
N2A—C24A—H24C | 109.5 | N2B—C24B—H24F | 109.5 |
H24A—C24A—H24C | 109.5 | H24D—C24B—H24F | 109.5 |
H24B—C24A—H24C | 109.5 | H24E—C24B—H24F | 109.5 |
C26A—C25A—C4A | 115.1 (2) | C26B—C25B—C4B | 115.7 (2) |
C26A—C25A—H25A | 108.5 | C26B—C25B—H25C | 108.4 |
C4A—C25A—H25A | 108.5 | C4B—C25B—H25C | 108.4 |
C26A—C25A—H25B | 108.5 | C26B—C25B—H25D | 108.4 |
C4A—C25A—H25B | 108.5 | C4B—C25B—H25D | 108.4 |
H25A—C25A—H25B | 107.5 | H25C—C25B—H25D | 107.4 |
C25A—C26A—H26A | 109.5 | C25B—C26B—H26D | 109.5 |
C25A—C26A—H26B | 109.5 | C25B—C26B—H26E | 109.5 |
H26A—C26A—H26B | 109.5 | H26D—C26B—H26E | 109.5 |
C25A—C26A—H26C | 109.5 | C25B—C26B—H26F | 109.5 |
H26A—C26A—H26C | 109.5 | H26D—C26B—H26F | 109.5 |
H26B—C26A—H26C | 109.5 | H26E—C26B—H26F | 109.5 |
O2A—S1A—N1A—C1A | 176.48 (15) | O2B—S1B—N1B—C1B | 175.40 (17) |
O1A—S1A—N1A—C1A | 46.62 (18) | O1B—S1B—N1B—C1B | 45.15 (19) |
C8A—S1A—N1A—C1A | −68.96 (18) | C8B—S1B—N1B—C1B | −69.89 (19) |
O2A—S1A—N1A—C4A | −47.70 (18) | O2B—S1B—N1B—C4B | −48.0 (2) |
O1A—S1A—N1A—C4A | −177.56 (15) | O1B—S1B—N1B—C4B | −178.22 (17) |
C8A—S1A—N1A—C4A | 66.86 (18) | C8B—S1B—N1B—C4B | 66.7 (2) |
C4A—N1A—C1A—C2A | −22.5 (2) | C4B—N1B—C1B—C2B | −21.8 (2) |
S1A—N1A—C1A—C2A | 116.49 (16) | S1B—N1B—C1B—C2B | 117.67 (17) |
N1A—C1A—C2A—C5A | 166.83 (18) | N1B—C1B—C2B—C5B | 165.9 (2) |
N1A—C1A—C2A—C3A | 40.9 (2) | N1B—C1B—C2B—C3B | 39.9 (2) |
C1A—C2A—C3A—C7A | −174.14 (17) | C5B—C2B—C3B—C7B | 56.4 (2) |
C5A—C2A—C3A—C7A | 55.5 (2) | C1B—C2B—C3B—C7B | −173.54 (18) |
C1A—C2A—C3A—C4A | −44.7 (2) | C5B—C2B—C3B—C4B | −173.86 (18) |
C5A—C2A—C3A—C4A | −175.14 (17) | C1B—C2B—C3B—C4B | −43.8 (2) |
C1A—N1A—C4A—C25A | −130.1 (2) | C1B—N1B—C4B—C25B | −130.4 (2) |
S1A—N1A—C4A—C25A | 91.3 (2) | S1B—N1B—C4B—C25B | 90.5 (2) |
C1A—N1A—C4A—C3A | −4.6 (2) | C1B—N1B—C4B—C3B | −4.7 (2) |
S1A—N1A—C4A—C3A | −143.16 (15) | S1B—N1B—C4B—C3B | −143.86 (16) |
C7A—C3A—C4A—N1A | 149.90 (19) | C7B—C3B—C4B—N1B | 149.9 (2) |
C2A—C3A—C4A—N1A | 29.8 (2) | C2B—C3B—C4B—N1B | 29.5 (2) |
C7A—C3A—C4A—C25A | −90.1 (3) | C7B—C3B—C4B—C25B | −90.2 (3) |
C2A—C3A—C4A—C25A | 149.78 (19) | C2B—C3B—C4B—C25B | 149.5 (2) |
C6A—O3A—C5A—C15A | 151.29 (18) | C6B—O3B—C5B—C2B | 28.9 (3) |
C6A—O3A—C5A—C2A | 32.6 (2) | C6B—O3B—C5B—C15B | 147.3 (2) |
C6A—O3A—C5A—C16A | −90.6 (2) | C6B—O3B—C5B—C16B | −94.7 (2) |
C1A—C2A—C5A—O3A | −179.95 (18) | C1B—C2B—C5B—O3B | −177.9 (2) |
C3A—C2A—C5A—O3A | −59.0 (2) | C3B—C2B—C5B—O3B | −57.1 (2) |
C1A—C2A—C5A—C15A | 66.8 (3) | C1B—C2B—C5B—C15B | 69.1 (3) |
C3A—C2A—C5A—C15A | −172.27 (18) | C3B—C2B—C5B—C15B | −170.18 (19) |
C1A—C2A—C5A—C16A | −61.2 (3) | C1B—C2B—C5B—C16B | −59.1 (3) |
C3A—C2A—C5A—C16A | 59.7 (2) | C3B—C2B—C5B—C16B | 61.7 (3) |
C5A—O3A—C6A—C7A | −4.6 (3) | C5B—O3B—C6B—C7B | −1.8 (3) |
C5A—O3A—C6A—C17A | 176.12 (18) | C5B—O3B—C6B—C17B | 178.79 (19) |
O3A—C6A—C7A—C23A | 175.99 (19) | O3B—C6B—C7B—C23B | 179.2 (2) |
C17A—C6A—C7A—C23A | −4.8 (3) | C17B—C6B—C7B—C23B | −1.5 (3) |
O3A—C6A—C7A—C3A | 0.6 (3) | O3B—C6B—C7B—C3B | 1.0 (3) |
C17A—C6A—C7A—C3A | 179.80 (19) | C17B—C6B—C7B—C3B | −179.7 (2) |
C2A—C3A—C7A—C6A | −25.3 (3) | C2B—C3B—C7B—C6B | −27.3 (3) |
C4A—C3A—C7A—C6A | −143.2 (2) | C4B—C3B—C7B—C6B | −145.7 (2) |
C2A—C3A—C7A—C23A | 159.40 (19) | C2B—C3B—C7B—C23B | 154.5 (2) |
C4A—C3A—C7A—C23A | 41.5 (3) | C4B—C3B—C7B—C23B | 36.2 (3) |
O2A—S1A—C8A—C9A | 20.4 (2) | O2B—S1B—C8B—C13B | −158.5 (2) |
O1A—S1A—C8A—C9A | 150.68 (19) | O1B—S1B—C8B—C13B | −28.1 (2) |
N1A—S1A—C8A—C9A | −94.2 (2) | N1B—S1B—C8B—C13B | 86.6 (2) |
O2A—S1A—C8A—C13A | −161.33 (19) | O2B—S1B—C8B—C9B | 23.2 (2) |
O1A—S1A—C8A—C13A | −31.1 (2) | O1B—S1B—C8B—C9B | 153.66 (19) |
N1A—S1A—C8A—C13A | 84.1 (2) | N1B—S1B—C8B—C9B | −91.6 (2) |
C13A—C8A—C9A—C10A | −0.5 (4) | C13B—C8B—C9B—C10B | −1.3 (4) |
S1A—C8A—C9A—C10A | 177.74 (18) | S1B—C8B—C9B—C10B | 176.99 (19) |
C8A—C9A—C10A—C11A | 0.0 (4) | C8B—C9B—C10B—C11B | −0.4 (4) |
C9A—C10A—C11A—C12A | 0.4 (4) | C9B—C10B—C11B—C12B | 1.4 (4) |
C9A—C10A—C11A—C14A | −177.1 (2) | C9B—C10B—C11B—C14B | −175.7 (3) |
C10A—C11A—C12A—C13A | −0.3 (4) | C10B—C11B—C12B—C13B | −0.8 (5) |
C14A—C11A—C12A—C13A | 177.2 (2) | C14B—C11B—C12B—C13B | 176.3 (3) |
C9A—C8A—C13A—C12A | 0.6 (4) | C9B—C8B—C13B—C12B | 1.9 (4) |
S1A—C8A—C13A—C12A | −177.62 (18) | S1B—C8B—C13B—C12B | −176.4 (2) |
C11A—C12A—C13A—C8A | −0.2 (4) | C11B—C12B—C13B—C8B | −0.9 (4) |
O3A—C6A—C17A—C18A | −0.1 (3) | O3B—C6B—C17B—C22B | −179.0 (2) |
C7A—C6A—C17A—C18A | −179.4 (2) | C7B—C6B—C17B—C22B | 1.6 (3) |
O3A—C6A—C17A—C22A | 178.89 (18) | O3B—C6B—C17B—C18B | 1.9 (3) |
C7A—C6A—C17A—C22A | −0.4 (3) | C7B—C6B—C17B—C18B | −177.5 (2) |
C22A—C17A—C18A—C19A | 0.0 (3) | C22B—C17B—C18B—C19B | 0.6 (3) |
C6A—C17A—C18A—C19A | 179.0 (2) | C6B—C17B—C18B—C19B | 179.6 (2) |
C17A—C18A—C19A—C20A | −0.4 (3) | C17B—C18B—C19B—C20B | 0.3 (4) |
C18A—C19A—C20A—C21A | 0.8 (4) | C18B—C19B—C20B—C21B | −0.4 (4) |
C19A—C20A—C21A—C22A | −0.7 (3) | C19B—C20B—C21B—C22B | −0.4 (4) |
C23A—N2A—C22A—C17A | 3.2 (3) | C23B—N2B—C22B—C17B | 0.4 (3) |
C24A—N2A—C22A—C17A | 178.0 (2) | C24B—N2B—C22B—C17B | 179.3 (2) |
C23A—N2A—C22A—C21A | −176.5 (2) | C23B—N2B—C22B—C21B | 179.9 (2) |
C24A—N2A—C22A—C21A | −1.6 (3) | C24B—N2B—C22B—C21B | −1.2 (3) |
C18A—C17A—C22A—N2A | −179.6 (2) | C18B—C17B—C22B—N2B | 178.1 (2) |
C6A—C17A—C22A—N2A | 1.4 (3) | C6B—C17B—C22B—N2B | −1.0 (3) |
C18A—C17A—C22A—C21A | 0.1 (3) | C18B—C17B—C22B—C21B | −1.4 (3) |
C6A—C17A—C22A—C21A | −179.0 (2) | C6B—C17B—C22B—C21B | 179.5 (2) |
C20A—C21A—C22A—N2A | 180.0 (2) | C20B—C21B—C22B—N2B | −178.1 (2) |
C20A—C21A—C22A—C17A | 0.3 (3) | C20B—C21B—C22B—C17B | 1.3 (3) |
C22A—N2A—C23A—O4A | 171.4 (2) | C22B—N2B—C23B—O4B | 179.4 (2) |
C24A—N2A—C23A—O4A | −3.6 (3) | C24B—N2B—C23B—O4B | 0.5 (3) |
C22A—N2A—C23A—C7A | −8.3 (3) | C22B—N2B—C23B—C7B | −0.3 (3) |
C24A—N2A—C23A—C7A | 176.72 (19) | C24B—N2B—C23B—C7B | −179.2 (2) |
C6A—C7A—C23A—O4A | −170.7 (2) | C6B—C7B—C23B—O4B | −178.9 (2) |
C3A—C7A—C23A—O4A | 4.6 (3) | C3B—C7B—C23B—O4B | −0.7 (3) |
C6A—C7A—C23A—N2A | 9.0 (3) | C6B—C7B—C23B—N2B | 0.8 (3) |
C3A—C7A—C23A—N2A | −175.71 (19) | C3B—C7B—C23B—N2B | 179.0 (2) |
N1A—C4A—C25A—C26A | 77.8 (3) | N1B—C4B—C25B—C26B | 82.2 (3) |
C3A—C4A—C25A—C26A | −38.1 (3) | C3B—C4B—C25B—C26B | −33.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C25A—H25A···O4A | 0.97 | 2.27 | 2.915 (3) | 123 |
C25A—H25B···O2A | 0.97 | 2.53 | 3.182 (3) | 125 |
C25B—H25C···O4B | 0.97 | 2.29 | 2.916 (4) | 121 |
C25B—H25D···O2B | 0.97 | 2.52 | 3.170 (4) | 124 |
C10A—H10A···O4Ai | 0.93 | 2.41 | 3.279 (3) | 155 |
C24A—H24A···O2Ai | 0.96 | 2.58 | 3.466 (3) | 153 |
C10B—H10B···O4Bii | 0.93 | 2.36 | 3.273 (4) | 167 |
C24B—H24E···O2Bii | 0.96 | 2.49 | 3.406 (4) | 159 |
C16A—H16C···Cg1iii | 0.96 | 2.81 | 3.416 (2) | 122 |
C20A—H20A···Cg2iv | 0.93 | 2.87 | 3.631 (3) | 140 |
C16B—H16D···Cg4v | 0.96 | 2.90 | 3.612 (3) | 131 |
C20B—H20B···Cg5vi | 0.93 | 2.82 | 3.589 (3) | 141 |
C12A—H12A···Cg5vii | 0.93 | 2.87 | 3.782 (3) | 166 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1; (v) −x, −y+1, −z+1; (vi) −x, −y+2, −z+1; (vii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C26H30N2O4S |
Mr | 466.58 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 24.7027 (7), 10.2685 (3), 19.6195 (5) |
β (°) | 109.554 (1) |
V (Å3) | 4689.7 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.17 |
Crystal size (mm) | 0.29 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEX2 CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.951, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 45928, 13623, 9445 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.705 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.067, 0.166, 1.03 |
No. of reflections | 13623 |
No. of parameters | 599 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.44, −0.47 |
Computer programs: APEX2 (Bruker, 2005), APEX2, SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C25A—H25A···O4A | 0.97 | 2.27 | 2.915 (3) | 123 |
C25A—H25B···O2A | 0.97 | 2.53 | 3.182 (3) | 125 |
C25B—H25C···O4B | 0.97 | 2.29 | 2.916 (4) | 121 |
C25B—H25D···O2B | 0.97 | 2.52 | 3.170 (4) | 124 |
C10A—H10A···O4Ai | 0.93 | 2.41 | 3.279 (3) | 155 |
C24A—H24A···O2Ai | 0.96 | 2.58 | 3.466 (3) | 153 |
C10B—H10B···O4Bii | 0.93 | 2.36 | 3.273 (4) | 167 |
C24B—H24E···O2Bii | 0.96 | 2.49 | 3.406 (4) | 159 |
C16A—H16C···Cg1iii | 0.96 | 2.81 | 3.416 (2) | 122 |
C20A—H20A···Cg2iv | 0.93 | 2.87 | 3.631 (3) | 140 |
C16B—H16D···Cg4v | 0.96 | 2.90 | 3.612 (3) | 131 |
C20B—H20B···Cg5vi | 0.93 | 2.82 | 3.589 (3) | 141 |
C12A—H12A···Cg5vii | 0.93 | 2.87 | 3.782 (3) | 166 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1; (v) −x, −y+1, −z+1; (vi) −x, −y+2, −z+1; (vii) x, y−1, z. |
Previously, we have reported the crystal structure of cis-1-ethyl-4,4,10-trimethyl-2-tosyl-1,2,3,3a,4,11b-hexahydro-11H- pyrrolo[3,4-c]pyrano[5,6-c]quinolin-11-one (Chinnakali et al., 2007). Now we report the crystal structure of the title compound, the trans-isomer.
The asymmetric unit of the title compound consists of two independent molecules, A and B, with quite similar conformations (Fig. 1). A superposition of the non-H atoms of molecules A and B (Fig. 2) using XP in SHELXTL (Sheldrick, 1998), gave an r.m.s. deviation of 0.086 Å. The pyrrolidine ring in both molecules is trans-fused to the dihydropyran ring.
The pyrrolidine ring in each molecule A and B adopts an envelope conformation, with the local mirror plane passing through C2 and the mid-point of the bond N1—C4. The relevant asymmetry parameters (Duax et al., 1976) are ΔCs[C2] = 5.8 (2)° for molecule A and 6.0 (2)° for molecule B; the puckering parameters Q and ϕ (Cremer & Pople, 1975) are 0.438 (2) Å and 78.9 (3)° for molecule A, and 0.429 (3) Å and 79.3 (3)° for molecule B. In the cis-isomer, the pyrrolidine ring adopts a twist conformation. In both molecules, the tosyl group is attached to the pyrrolidine ring in a biaxial position. The sum of the bond angles around atom N1 of the molecules A (345.6°) and B (348.0°) indicates sp3 hybridization.
In both molecules, the dihydropyran ring also adopts an envelope conformation, with the local mirror plane passing through atoms C2 and C6. The asymmetry parameter ΔCs[C2] is 5.2 (2)° for molecule A and 1.1 (2)° for molecule B; the puckering parameters Q, θ and ϕ are 0.493 (2) Å, 128.6 (2)° and 294.1 (3)° for molecule A, and 0.486 (3) Å, 128.0 (2)° and 299.1 (4)° for molecule B. In the cis-isomer, the dihydropyran ring is in a half-chair conformation. In both molecules, the sulfonyl group has distorted tetrahedral geometry [O2A—S1A—O1A = 120.04 (11)° and O2B—S1B—O1B = 120.47 (12)°]; the quinolinone ring system is planar, with an r.m.s. deviation of 0.026 Å in molecule A and 0.014 Å in molecule B.
A superposition of the non-H atoms in the quinolinone ring systems of molecule A or B and cis-isomer (Chinnakali et al., 2007) (Fig. 2) shows that the overall conformations of the cis and trans isomers are different. In the cis-isomer, the molecule is in a folded conformation, with the sulfonyl-bound phenyl ring lying over the pyridinone ring. But in the trans-isomer, though the tosyl group is slightly bent towards the fused ring system, it is not lying over the pyridinone ring. The trans-fusion results in an extended ring system.
The A molecules are linked into a chain along the b axis by C10A—H10A···O4Ai and C24A—H24A···O2Ai hydrogen bonds (symmetry code as in Table 1). Inversion-related molecules of the adjacent A chains are cross-linked into a two-dimensional network parallel to the bc plane via C16A—H16C···π interactions involving the N2A/C22A/C17A/C6A/C7A/C23A ring (centroid Cg1) of the molecules at (1 - x, 1 - y, 1 - z), C20A—H20A···π interactions involving the C8A—C13A ring (centroid Cg2) of the molecules at (1 - x, -y, 1 - z), and π-π interactions involving the C17A—C22A rings (centroid Cg3) of the molecules at (x, y, z) and (1 - x,-y,1 - z) [centroid-centroid distance is 3.5477 (13) Å].
Similarly, the B molecules are linked into a chain along the b axis by C10B—H10B···O4Bii and C24B—H24E···O2Bii hydrogen bonds (symmetry code as in Table 1). Inversion-related molecules of the adjacent B chains are cross-linked into a two-dimensional network parallel to the bc plane via C16B—H16D···π interactions involving the N2B/C22B/C17B/C6B/C7B/C23B ring (centroid Cg4) of the molecules at (-x, 1 - y, 1 - z), C20B—H20B···π interactions involving the C8B—C13B ring (centroid Cg5) of the molecules at (-x, 2 - y, 1 - z), and π-π interactions involving the C17B—C22B ring (centroid Cg6) of the molecules at (x, y, z) and (-x,2 - y,1 - z) [centroid-centroid distance is 3.5743 (15) Å].
The two-dimensional networks formed by the A and B molecules are arranged alternately along the a axis, and are linked via C12A—H12A···π interactions involving the C8B—C13B ring (centroid Cg5).