Solvates of the antifungal drug griseofulvin: structural, thermochemical and conformational analysis
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520613026711/zb5031sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520613026711/zb5031GF-MeCNsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520613026711/zb5031GF-NMsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520613026711/zb5031GF-NE2-1sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520613026711/zb5031GF-NE1-1sup5.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520613026711/zb5031sup6.pdf | |
Text file https://doi.org/10.1107/S2052520613026711/zb5031sup7.txt | |
Text file https://doi.org/10.1107/S2052520613026711/zb5031sup8.txt |
CCDC references: 924889; 924890; 924891; 924892
For all compounds, data collection: CrystalClear (Rigaku Inc., 2007); cell refinement: CrystalClear (Rigaku Inc., 2007); data reduction: CrystalClear (Rigaku Inc., 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).
C19H20ClNO6 | F(000) = 824 |
Mr = 393.81 | Dx = 1.355 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 4495 reflections |
a = 11.783 (2) Å | θ = 2.1–31.2° |
b = 8.5387 (17) Å | µ = 0.23 mm−1 |
c = 19.297 (4) Å | T = 110 K |
β = 96.03 (3)° | Block, colorless |
V = 1930.8 (7) Å3 | 0.33 × 0.22 × 0.22 mm |
Z = 4 |
Rigaku Saturn 70 CCD area detector diffractometer | 8585 independent reflections |
Radiation source: fine-focus sealed tube | 8103 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω scans | θmax = 28.3°, θmin = 1.7° |
Absorption correction: multi-scan R. H. Blessing, Acta Cryst. 1995 A51, 33-38 | h = −15→15 |
Tmin = 0.927, Tmax = 0.951 | k = −7→11 |
27812 measured reflections | l = −25→25 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.152 | w = 1/[σ2(Fo2) + (0.0812P)2 + 0.660P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
8585 reflections | Δρmax = 0.72 e Å−3 |
497 parameters | Δρmin = −0.38 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.05 (5) |
C19H20ClNO6 | V = 1930.8 (7) Å3 |
Mr = 393.81 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 11.783 (2) Å | µ = 0.23 mm−1 |
b = 8.5387 (17) Å | T = 110 K |
c = 19.297 (4) Å | 0.33 × 0.22 × 0.22 mm |
β = 96.03 (3)° |
Rigaku Saturn 70 CCD area detector diffractometer | 8585 independent reflections |
Absorption correction: multi-scan R. H. Blessing, Acta Cryst. 1995 A51, 33-38 | 8103 reflections with I > 2σ(I) |
Tmin = 0.927, Tmax = 0.951 | Rint = 0.030 |
27812 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.152 | Δρmax = 0.72 e Å−3 |
S = 1.12 | Δρmin = −0.38 e Å−3 |
8585 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
497 parameters | Absolute structure parameter: 0.05 (5) |
1 restraint |
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 | ||
Cl1 | 0.17274 (5) | −0.38730 (7) | 0.57342 (3) | 0.0274 (3) | |
O6 | 0.07655 (16) | 0.2852 (2) | 0.60335 (10) | 0.0283 (5) | |
O5 | −0.05399 (16) | −0.2508 (2) | 0.57137 (10) | 0.0280 (5) | |
O2 | 0.41387 (17) | 0.0290 (2) | 0.48152 (9) | 0.0296 (5) | |
O3 | 0.33767 (15) | −0.1177 (2) | 0.58766 (9) | 0.0252 (4) | |
O4 | 0.33621 (17) | 0.2953 (3) | 0.61322 (12) | 0.0347 (5) | |
C12 | 0.1396 (2) | −0.1917 (3) | 0.57868 (13) | 0.0231 (5) | |
C10 | 0.0019 (2) | 0.0204 (3) | 0.58558 (13) | 0.0234 (5) | |
H10 | −0.0752 | 0.0537 | 0.5847 | 0.028* | |
C13 | 0.2248 (2) | −0.0810 (3) | 0.58558 (13) | 0.0226 (5) | |
C9 | 0.0902 (2) | 0.1297 (3) | 0.59381 (12) | 0.0227 (5) | |
C3 | 0.4750 (2) | 0.0562 (3) | 0.54332 (13) | 0.0260 (6) | |
C5 | 0.4759 (2) | 0.0011 (4) | 0.67142 (14) | 0.0298 (6) | |
H5 | 0.5173 | −0.1005 | 0.6681 | 0.036* | |
C4 | 0.4027 (2) | 0.0244 (3) | 0.60253 (13) | 0.0251 (6) | |
C2 | 0.5817 (2) | 0.1114 (4) | 0.55394 (15) | 0.0343 (7) | |
H2 | 0.6232 | 0.1286 | 0.5150 | 0.041* | |
C11 | 0.0271 (2) | −0.1379 (3) | 0.57867 (13) | 0.0237 (6) | |
C17 | −0.0362 (2) | 0.3414 (4) | 0.61033 (15) | 0.0295 (6) | |
H17A | −0.0868 | 0.3141 | 0.5685 | 0.044* | |
H17B | −0.0343 | 0.4554 | 0.6160 | 0.044* | |
H17C | −0.0646 | 0.2930 | 0.6512 | 0.044* | |
C8 | 0.2038 (2) | 0.0785 (3) | 0.59394 (12) | 0.0245 (6) | |
C6 | 0.5659 (2) | 0.1282 (4) | 0.68391 (15) | 0.0354 (7) | |
H6A | 0.5282 | 0.2291 | 0.6921 | 0.042* | |
H6B | 0.6174 | 0.1025 | 0.7263 | 0.042* | |
C16 | −0.1709 (2) | −0.2067 (4) | 0.57173 (16) | 0.0318 (6) | |
H16A | −0.1820 | −0.1583 | 0.6166 | 0.048* | |
H16B | −0.2193 | −0.2999 | 0.5648 | 0.048* | |
H16C | −0.1916 | −0.1318 | 0.5341 | 0.048* | |
C7 | 0.3120 (2) | 0.1568 (3) | 0.60419 (14) | 0.0270 (6) | |
C14 | 0.4039 (3) | −0.0134 (5) | 0.73274 (15) | 0.0412 (8) | |
H14A | 0.3682 | 0.0877 | 0.7408 | 0.062* | |
H14B | 0.4530 | −0.0444 | 0.7747 | 0.062* | |
H14C | 0.3446 | −0.0927 | 0.7220 | 0.062* | |
O1 | 0.7343 (2) | 0.1935 (5) | 0.63221 (15) | 0.0749 (11) | |
C1 | 0.6354 (3) | 0.1454 (4) | 0.62303 (17) | 0.0411 (8) | |
C15 | 0.4690 (3) | 0.0644 (4) | 0.41999 (15) | 0.0390 (7) | |
H15A | 0.4963 | 0.1729 | 0.4224 | 0.059* | |
H15B | 0.4144 | 0.0510 | 0.3785 | 0.059* | |
H15C | 0.5338 | −0.0065 | 0.4174 | 0.059* | |
Cl2 | 0.33007 (5) | −0.34949 (7) | 0.92510 (3) | 0.0266 (2) | |
O2A | 0.09083 (16) | 0.0651 (2) | 1.02207 (9) | 0.0268 (4) | |
O5A | 0.55669 (16) | −0.2131 (2) | 0.92697 (10) | 0.0278 (5) | |
O4A | 0.16645 (16) | 0.3338 (2) | 0.89310 (11) | 0.0301 (5) | |
O6A | 0.42572 (15) | 0.3235 (2) | 0.89871 (10) | 0.0275 (5) | |
O3A | 0.16576 (15) | −0.0801 (2) | 0.91476 (10) | 0.0233 (4) | |
C10A | 0.5010 (2) | 0.0596 (3) | 0.91456 (12) | 0.0226 (5) | |
H10A | 0.5779 | 0.0932 | 0.9148 | 0.027* | |
C12A | 0.3634 (2) | −0.1535 (3) | 0.92137 (12) | 0.0217 (5) | |
C4A | 0.1003 (2) | 0.0626 (3) | 0.90149 (13) | 0.0226 (5) | |
C13A | 0.2781 (2) | −0.0428 (3) | 0.91600 (12) | 0.0230 (5) | |
C17A | 0.5383 (2) | 0.3794 (4) | 0.88976 (16) | 0.0304 (6) | |
H17D | 0.5908 | 0.3506 | 0.9305 | 0.046* | |
H17E | 0.5366 | 0.4936 | 0.8847 | 0.046* | |
H17F | 0.5642 | 0.3321 | 0.8479 | 0.046* | |
C5A | 0.0272 (2) | 0.0418 (3) | 0.83159 (13) | 0.0266 (6) | |
H5A | −0.0128 | −0.0611 | 0.8336 | 0.032* | |
C9A | 0.4130 (2) | 0.1685 (3) | 0.90752 (13) | 0.0232 (5) | |
C16A | 0.6738 (2) | −0.1686 (4) | 0.92828 (16) | 0.0320 (6) | |
H16D | 0.6859 | −0.1166 | 0.8844 | 0.048* | |
H16E | 0.7221 | −0.2621 | 0.9341 | 0.048* | |
H16F | 0.6937 | −0.0966 | 0.9672 | 0.048* | |
C11A | 0.4762 (2) | −0.1000 (3) | 0.92128 (12) | 0.0222 (5) | |
C8A | 0.2991 (2) | 0.1169 (3) | 0.90873 (12) | 0.0223 (5) | |
C2A | −0.0793 (2) | 0.1430 (4) | 0.95125 (14) | 0.0304 (6) | |
H2A | −0.1202 | 0.1581 | 0.9906 | 0.037* | |
O1A | −0.2347 (2) | 0.2197 (4) | 0.87353 (14) | 0.0576 (8) | |
C3A | 0.0287 (2) | 0.0903 (3) | 0.96098 (13) | 0.0239 (5) | |
C6A | −0.0647 (2) | 0.1674 (4) | 0.82138 (15) | 0.0323 (6) | |
H6AA | −0.0282 | 0.2701 | 0.8150 | 0.039* | |
H6AB | −0.1157 | 0.1441 | 0.7785 | 0.039* | |
C7A | 0.1908 (2) | 0.1954 (3) | 0.90038 (13) | 0.0250 (5) | |
C14A | 0.0994 (3) | 0.0334 (4) | 0.77016 (14) | 0.0345 (7) | |
H14D | 0.0504 | 0.0066 | 0.7276 | 0.052* | |
H14E | 0.1584 | −0.0470 | 0.7794 | 0.052* | |
H14F | 0.1356 | 0.1351 | 0.7642 | 0.052* | |
C15A | 0.0374 (3) | 0.0976 (4) | 1.08422 (14) | 0.0357 (7) | |
H15D | 0.0085 | 0.2053 | 1.0825 | 0.054* | |
H15E | 0.0935 | 0.0850 | 1.1251 | 0.054* | |
H15F | −0.0260 | 0.0247 | 1.0874 | 0.054* | |
C1A | −0.1351 (2) | 0.1777 (4) | 0.88225 (16) | 0.0361 (7) | |
C19 | 0.1418 (4) | 0.5705 (5) | 0.75574 (17) | 0.0517 (9) | |
C18 | 0.2531 (3) | 0.5048 (6) | 0.75057 (15) | 0.0522 (10) | |
H18A | 0.2490 | 0.4304 | 0.7117 | 0.078* | |
H18B | 0.2793 | 0.4504 | 0.7940 | 0.078* | |
H18C | 0.3067 | 0.5889 | 0.7425 | 0.078* | |
N1 | 0.0511 (4) | 0.6227 (6) | 0.75849 (19) | 0.0726 (11) | |
C20 | 0.2377 (5) | −0.0165 (9) | 0.2543 (2) | 0.113 (3) | |
H20A | 0.2743 | −0.0752 | 0.2191 | 0.169* | |
H20B | 0.1546 | −0.0245 | 0.2445 | 0.169* | |
H20C | 0.2614 | −0.0601 | 0.3006 | 0.169* | |
C21 | 0.2732 (8) | 0.1546 (12) | 0.2525 (3) | 0.158 (5) | |
N2 | 0.3132 (13) | 0.2683 (12) | 0.2498 (3) | 0.281 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0273 (4) | 0.0222 (7) | 0.0331 (3) | −0.0018 (2) | 0.0047 (3) | −0.0012 (2) |
O6 | 0.0225 (9) | 0.0206 (12) | 0.0427 (10) | −0.0006 (7) | 0.0082 (8) | −0.0030 (8) |
O5 | 0.0214 (9) | 0.0277 (12) | 0.0348 (10) | −0.0062 (8) | 0.0017 (7) | −0.0020 (8) |
O2 | 0.0293 (10) | 0.0330 (13) | 0.0275 (9) | 0.0001 (8) | 0.0078 (7) | 0.0014 (8) |
O3 | 0.0202 (9) | 0.0244 (12) | 0.0316 (9) | −0.0017 (7) | 0.0060 (7) | −0.0024 (8) |
O4 | 0.0266 (10) | 0.0252 (12) | 0.0535 (13) | −0.0061 (8) | 0.0104 (9) | −0.0082 (9) |
C12 | 0.0209 (12) | 0.0222 (15) | 0.0260 (11) | −0.0010 (10) | 0.0005 (9) | 0.0000 (10) |
C10 | 0.0186 (11) | 0.0261 (15) | 0.0254 (11) | −0.0029 (10) | 0.0024 (9) | −0.0002 (10) |
C13 | 0.0145 (11) | 0.0276 (16) | 0.0263 (11) | −0.0026 (9) | 0.0046 (8) | 0.0000 (10) |
C9 | 0.0215 (12) | 0.0215 (15) | 0.0260 (11) | −0.0014 (10) | 0.0060 (9) | −0.0003 (10) |
C3 | 0.0261 (13) | 0.0256 (15) | 0.0274 (11) | 0.0004 (10) | 0.0072 (9) | 0.0005 (10) |
C5 | 0.0248 (13) | 0.0363 (18) | 0.0286 (12) | −0.0042 (11) | 0.0050 (10) | −0.0043 (11) |
C4 | 0.0221 (12) | 0.0247 (15) | 0.0289 (12) | −0.0030 (10) | 0.0048 (9) | −0.0042 (10) |
C2 | 0.0239 (13) | 0.041 (2) | 0.0410 (14) | −0.0036 (12) | 0.0154 (11) | 0.0001 (13) |
C11 | 0.0220 (12) | 0.0265 (15) | 0.0227 (11) | −0.0070 (10) | 0.0027 (9) | −0.0019 (10) |
C17 | 0.0225 (13) | 0.0281 (16) | 0.0389 (14) | 0.0000 (11) | 0.0081 (10) | −0.0039 (11) |
C8 | 0.0205 (12) | 0.0278 (16) | 0.0259 (11) | −0.0029 (10) | 0.0062 (9) | −0.0027 (10) |
C6 | 0.0261 (14) | 0.044 (2) | 0.0359 (14) | −0.0042 (13) | 0.0013 (11) | −0.0112 (13) |
C16 | 0.0195 (12) | 0.0300 (16) | 0.0457 (15) | −0.0049 (11) | 0.0018 (11) | −0.0014 (12) |
C7 | 0.0224 (12) | 0.0266 (16) | 0.0333 (13) | −0.0047 (11) | 0.0093 (10) | −0.0034 (11) |
C14 | 0.0356 (16) | 0.060 (2) | 0.0284 (14) | −0.0067 (15) | 0.0049 (12) | −0.0008 (14) |
O1 | 0.0330 (14) | 0.128 (3) | 0.0646 (17) | −0.0385 (17) | 0.0107 (12) | −0.0190 (19) |
C1 | 0.0256 (14) | 0.049 (2) | 0.0494 (17) | −0.0094 (14) | 0.0069 (12) | −0.0076 (15) |
C15 | 0.0401 (17) | 0.048 (2) | 0.0312 (13) | 0.0010 (15) | 0.0145 (12) | 0.0040 (13) |
Cl2 | 0.0254 (3) | 0.0189 (6) | 0.0358 (3) | 0.0017 (2) | 0.0045 (3) | 0.0015 (2) |
O2A | 0.0265 (9) | 0.0291 (12) | 0.0255 (8) | −0.0010 (8) | 0.0054 (7) | 0.0010 (7) |
O5A | 0.0200 (9) | 0.0246 (12) | 0.0386 (10) | 0.0064 (8) | 0.0023 (7) | 0.0001 (8) |
O4A | 0.0242 (10) | 0.0225 (12) | 0.0447 (11) | 0.0054 (8) | 0.0083 (8) | 0.0064 (8) |
O6A | 0.0177 (9) | 0.0206 (12) | 0.0452 (11) | 0.0004 (7) | 0.0076 (7) | 0.0029 (8) |
O3A | 0.0176 (8) | 0.0198 (11) | 0.0330 (9) | 0.0023 (7) | 0.0049 (7) | 0.0013 (7) |
C10A | 0.0162 (11) | 0.0254 (15) | 0.0264 (11) | 0.0024 (10) | 0.0027 (8) | −0.0005 (10) |
C12A | 0.0234 (12) | 0.0193 (14) | 0.0221 (11) | 0.0014 (10) | 0.0007 (9) | 0.0003 (9) |
C4A | 0.0159 (11) | 0.0209 (14) | 0.0315 (12) | 0.0014 (9) | 0.0051 (9) | 0.0020 (10) |
C13A | 0.0195 (11) | 0.0275 (15) | 0.0222 (11) | 0.0031 (10) | 0.0034 (9) | 0.0008 (10) |
C17A | 0.0191 (12) | 0.0251 (16) | 0.0483 (16) | 0.0000 (10) | 0.0095 (11) | 0.0026 (12) |
C5A | 0.0220 (12) | 0.0284 (16) | 0.0299 (12) | 0.0014 (10) | 0.0049 (9) | 0.0017 (10) |
C9A | 0.0210 (12) | 0.0208 (15) | 0.0285 (11) | 0.0007 (10) | 0.0054 (9) | −0.0030 (10) |
C16A | 0.0181 (12) | 0.0312 (17) | 0.0467 (16) | 0.0044 (11) | 0.0044 (11) | 0.0005 (12) |
C11A | 0.0174 (11) | 0.0250 (15) | 0.0244 (11) | 0.0054 (10) | 0.0035 (8) | 0.0000 (10) |
C8A | 0.0193 (11) | 0.0224 (15) | 0.0256 (11) | 0.0014 (10) | 0.0049 (9) | 0.0024 (9) |
C2A | 0.0236 (13) | 0.0344 (17) | 0.0350 (13) | 0.0041 (11) | 0.0109 (10) | −0.0006 (12) |
O1A | 0.0239 (11) | 0.087 (2) | 0.0619 (15) | 0.0208 (12) | 0.0058 (10) | 0.0132 (15) |
C3A | 0.0219 (12) | 0.0216 (14) | 0.0286 (11) | −0.0018 (10) | 0.0055 (9) | 0.0023 (10) |
C6A | 0.0221 (13) | 0.0383 (18) | 0.0364 (13) | 0.0040 (12) | 0.0031 (10) | 0.0095 (12) |
C7A | 0.0211 (12) | 0.0279 (15) | 0.0268 (11) | 0.0013 (10) | 0.0059 (9) | 0.0026 (10) |
C14A | 0.0327 (15) | 0.0420 (19) | 0.0289 (13) | 0.0030 (13) | 0.0041 (11) | 0.0013 (12) |
C15A | 0.0399 (16) | 0.0396 (19) | 0.0288 (13) | −0.0069 (14) | 0.0096 (11) | −0.0020 (12) |
C1A | 0.0225 (13) | 0.044 (2) | 0.0426 (15) | 0.0090 (12) | 0.0056 (11) | 0.0062 (14) |
C19 | 0.073 (3) | 0.045 (2) | 0.0376 (16) | −0.015 (2) | 0.0118 (16) | −0.0028 (15) |
C18 | 0.068 (3) | 0.052 (2) | 0.0369 (18) | −0.0002 (18) | 0.0091 (17) | 0.0033 (15) |
N1 | 0.065 (2) | 0.092 (3) | 0.062 (2) | −0.003 (2) | 0.0127 (18) | −0.010 (2) |
C20 | 0.157 (6) | 0.118 (6) | 0.056 (3) | −0.094 (5) | −0.024 (3) | 0.021 (3) |
C21 | 0.216 (9) | 0.198 (10) | 0.055 (3) | −0.176 (8) | −0.009 (4) | 0.003 (4) |
N2 | 0.560 (18) | 0.184 (9) | 0.079 (4) | −0.233 (12) | −0.060 (7) | 0.033 (4) |
Cl1—C12 | 1.721 (3) | O4A—C7A | 1.220 (4) |
O6—C9 | 1.352 (3) | O6A—C9A | 1.345 (3) |
O6—C17 | 1.432 (3) | O6A—C17A | 1.437 (3) |
O5—C11 | 1.354 (3) | O3A—C13A | 1.360 (3) |
O5—C16 | 1.429 (3) | O3A—C4A | 1.450 (3) |
O2—C3 | 1.347 (3) | C10A—C9A | 1.389 (3) |
O2—C15 | 1.444 (3) | C10A—C11A | 1.403 (4) |
O3—C13 | 1.363 (3) | C10A—H10A | 0.9500 |
O3—C4 | 1.448 (3) | C12A—C13A | 1.376 (4) |
O4—C7 | 1.225 (4) | C12A—C11A | 1.405 (3) |
C12—C13 | 1.376 (4) | C4A—C3A | 1.513 (3) |
C12—C11 | 1.402 (4) | C4A—C5A | 1.533 (4) |
C10—C11 | 1.394 (4) | C4A—C7A | 1.558 (4) |
C10—C9 | 1.394 (4) | C13A—C8A | 1.395 (4) |
C10—H10 | 0.9500 | C17A—H17D | 0.9800 |
C13—C8 | 1.397 (4) | C17A—H17E | 0.9800 |
C9—C8 | 1.408 (3) | C17A—H17F | 0.9800 |
C3—C2 | 1.338 (4) | C5A—C6A | 1.523 (4) |
C3—C4 | 1.520 (3) | C5A—C14A | 1.532 (4) |
C5—C6 | 1.519 (4) | C5A—H5A | 1.0000 |
C5—C4 | 1.520 (4) | C9A—C8A | 1.415 (3) |
C5—C14 | 1.532 (4) | C16A—H16D | 0.9800 |
C5—H5 | 1.0000 | C16A—H16E | 0.9800 |
C4—C7 | 1.559 (4) | C16A—H16F | 0.9800 |
C2—C1 | 1.444 (4) | C8A—C7A | 1.435 (4) |
C2—H2 | 0.9500 | C2A—C3A | 1.345 (4) |
C17—H17A | 0.9800 | C2A—C1A | 1.452 (4) |
C17—H17B | 0.9800 | C2A—H2A | 0.9500 |
C17—H17C | 0.9800 | O1A—C1A | 1.221 (4) |
C8—C7 | 1.434 (4) | C6A—C1A | 1.510 (4) |
C6—C1 | 1.508 (4) | C6A—H6AA | 0.9900 |
C6—H6A | 0.9900 | C6A—H6AB | 0.9900 |
C6—H6B | 0.9900 | C14A—H14D | 0.9800 |
C16—H16A | 0.9800 | C14A—H14E | 0.9800 |
C16—H16B | 0.9800 | C14A—H14F | 0.9800 |
C16—H16C | 0.9800 | C15A—H15D | 0.9800 |
C14—H14A | 0.9800 | C15A—H15E | 0.9800 |
C14—H14B | 0.9800 | C15A—H15F | 0.9800 |
C14—H14C | 0.9800 | C19—N1 | 1.164 (5) |
O1—C1 | 1.231 (4) | C19—C18 | 1.439 (5) |
C15—H15A | 0.9800 | C18—H18A | 0.9800 |
C15—H15B | 0.9800 | C18—H18B | 0.9800 |
C15—H15C | 0.9800 | C18—H18C | 0.9800 |
Cl2—C12A | 1.722 (3) | C20—C21 | 1.521 (11) |
O2A—C3A | 1.338 (3) | C20—H20A | 0.9800 |
O2A—C15A | 1.439 (3) | C20—H20B | 0.9800 |
O5A—C11A | 1.350 (3) | C20—H20C | 0.9800 |
O5A—C16A | 1.429 (3) | C21—N2 | 1.082 (9) |
C9—O6—C17 | 117.8 (2) | C13A—C12A—C11A | 117.4 (2) |
C11—O5—C16 | 118.9 (2) | C13A—C12A—Cl2 | 120.2 (2) |
C3—O2—C15 | 116.5 (2) | C11A—C12A—Cl2 | 122.4 (2) |
C13—O3—C4 | 107.9 (2) | O3A—C4A—C3A | 109.0 (2) |
C13—C12—C11 | 117.1 (3) | O3A—C4A—C5A | 107.3 (2) |
C13—C12—Cl1 | 120.3 (2) | C3A—C4A—C5A | 112.3 (2) |
C11—C12—Cl1 | 122.5 (2) | O3A—C4A—C7A | 105.19 (19) |
C11—C10—C9 | 119.7 (2) | C3A—C4A—C7A | 109.5 (2) |
C11—C10—H10 | 120.1 | C5A—C4A—C7A | 113.2 (2) |
C9—C10—H10 | 120.1 | O3A—C13A—C12A | 122.9 (3) |
O3—C13—C12 | 123.0 (3) | O3A—C13A—C8A | 114.2 (2) |
O3—C13—C8 | 113.9 (2) | C12A—C13A—C8A | 122.9 (2) |
C12—C13—C8 | 123.0 (2) | O6A—C17A—H17D | 109.5 |
O6—C9—C10 | 125.1 (2) | O6A—C17A—H17E | 109.5 |
O6—C9—C8 | 115.5 (2) | H17D—C17A—H17E | 109.5 |
C10—C9—C8 | 119.4 (3) | O6A—C17A—H17F | 109.5 |
C2—C3—O2 | 127.1 (2) | H17D—C17A—H17F | 109.5 |
C2—C3—C4 | 122.7 (2) | H17E—C17A—H17F | 109.5 |
O2—C3—C4 | 110.2 (2) | C6A—C5A—C14A | 112.2 (2) |
C6—C5—C4 | 111.6 (2) | C6A—C5A—C4A | 111.0 (2) |
C6—C5—C14 | 111.7 (2) | C14A—C5A—C4A | 112.3 (2) |
C4—C5—C14 | 112.1 (2) | C6A—C5A—H5A | 107.0 |
C6—C5—H5 | 107.0 | C14A—C5A—H5A | 107.0 |
C4—C5—H5 | 107.0 | C4A—C5A—H5A | 107.0 |
C14—C5—H5 | 107.0 | O6A—C9A—C10A | 125.4 (2) |
O3—C4—C3 | 109.1 (2) | O6A—C9A—C8A | 115.3 (2) |
O3—C4—C5 | 107.7 (2) | C10A—C9A—C8A | 119.4 (3) |
C3—C4—C5 | 111.7 (2) | O5A—C16A—H16D | 109.5 |
O3—C4—C7 | 105.2 (2) | O5A—C16A—H16E | 109.5 |
C3—C4—C7 | 109.0 (2) | H16D—C16A—H16E | 109.5 |
C5—C4—C7 | 113.9 (2) | O5A—C16A—H16F | 109.5 |
C3—C2—C1 | 121.7 (2) | H16D—C16A—H16F | 109.5 |
C3—C2—H2 | 119.1 | H16E—C16A—H16F | 109.5 |
C1—C2—H2 | 119.1 | O5A—C11A—C10A | 123.4 (2) |
O5—C11—C10 | 123.0 (2) | O5A—C11A—C12A | 115.1 (2) |
O5—C11—C12 | 115.1 (2) | C10A—C11A—C12A | 121.5 (2) |
C10—C11—C12 | 121.9 (2) | C13A—C8A—C9A | 118.9 (2) |
O6—C17—H17A | 109.5 | C13A—C8A—C7A | 107.7 (2) |
O6—C17—H17B | 109.5 | C9A—C8A—C7A | 133.3 (3) |
H17A—C17—H17B | 109.5 | C3A—C2A—C1A | 121.8 (2) |
O6—C17—H17C | 109.5 | C3A—C2A—H2A | 119.1 |
H17A—C17—H17C | 109.5 | C1A—C2A—H2A | 119.1 |
H17B—C17—H17C | 109.5 | O2A—C3A—C2A | 126.8 (2) |
C13—C8—C9 | 118.8 (2) | O2A—C3A—C4A | 110.3 (2) |
C13—C8—C7 | 107.7 (2) | C2A—C3A—C4A | 122.8 (2) |
C9—C8—C7 | 133.4 (3) | C1A—C6A—C5A | 112.4 (2) |
C1—C6—C5 | 111.9 (2) | C1A—C6A—H6AA | 109.1 |
C1—C6—H6A | 109.2 | C5A—C6A—H6AA | 109.1 |
C5—C6—H6A | 109.2 | C1A—C6A—H6AB | 109.1 |
C1—C6—H6B | 109.2 | C5A—C6A—H6AB | 109.1 |
C5—C6—H6B | 109.2 | H6AA—C6A—H6AB | 107.8 |
H6A—C6—H6B | 107.9 | O4A—C7A—C8A | 131.4 (3) |
O5—C16—H16A | 109.5 | O4A—C7A—C4A | 123.6 (2) |
O5—C16—H16B | 109.5 | C8A—C7A—C4A | 105.1 (2) |
H16A—C16—H16B | 109.5 | C5A—C14A—H14D | 109.5 |
O5—C16—H16C | 109.5 | C5A—C14A—H14E | 109.5 |
H16A—C16—H16C | 109.5 | H14D—C14A—H14E | 109.5 |
H16B—C16—H16C | 109.5 | C5A—C14A—H14F | 109.5 |
O4—C7—C8 | 131.3 (3) | H14D—C14A—H14F | 109.5 |
O4—C7—C4 | 123.6 (2) | H14E—C14A—H14F | 109.5 |
C8—C7—C4 | 105.1 (2) | O2A—C15A—H15D | 109.5 |
C5—C14—H14A | 109.5 | O2A—C15A—H15E | 109.5 |
C5—C14—H14B | 109.5 | H15D—C15A—H15E | 109.5 |
H14A—C14—H14B | 109.5 | O2A—C15A—H15F | 109.5 |
C5—C14—H14C | 109.5 | H15D—C15A—H15F | 109.5 |
H14A—C14—H14C | 109.5 | H15E—C15A—H15F | 109.5 |
H14B—C14—H14C | 109.5 | O1A—C1A—C2A | 121.5 (3) |
O1—C1—C2 | 121.1 (3) | O1A—C1A—C6A | 120.5 (3) |
O1—C1—C6 | 120.2 (3) | C2A—C1A—C6A | 117.9 (2) |
C2—C1—C6 | 118.6 (2) | N1—C19—C18 | 178.6 (4) |
O2—C15—H15A | 109.5 | C19—C18—H18A | 109.5 |
O2—C15—H15B | 109.5 | C19—C18—H18B | 109.5 |
H15A—C15—H15B | 109.5 | H18A—C18—H18B | 109.5 |
O2—C15—H15C | 109.5 | C19—C18—H18C | 109.5 |
H15A—C15—H15C | 109.5 | H18A—C18—H18C | 109.5 |
H15B—C15—H15C | 109.5 | H18B—C18—H18C | 109.5 |
C3A—O2A—C15A | 117.2 (2) | C21—C20—H20A | 109.5 |
C11A—O5A—C16A | 118.7 (2) | C21—C20—H20B | 109.5 |
C9A—O6A—C17A | 117.3 (2) | H20A—C20—H20B | 109.5 |
C13A—O3A—C4A | 107.7 (2) | C21—C20—H20C | 109.5 |
C9A—C10A—C11A | 119.9 (2) | H20A—C20—H20C | 109.5 |
C9A—C10A—H10A | 120.1 | H20B—C20—H20C | 109.5 |
C11A—C10A—H10A | 120.1 | N2—C21—C20 | 169.8 (16) |
C18H20ClNO8 | F(000) = 864 |
Mr = 413.80 | Dx = 1.422 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 5198 reflections |
a = 8.5456 (17) Å | θ = 2.0–31.1° |
b = 11.740 (2) Å | µ = 0.24 mm−1 |
c = 19.269 (4) Å | T = 110 K |
V = 1933.2 (6) Å3 | Block, colorless |
Z = 4 | 0.44 × 0.33 × 0.22 mm |
Rigaku Saturn 70 CCD area detector diffractometer | 4791 independent reflections |
Radiation source: fine-focus sealed tube | 4703 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
ω scans | θmax = 28.3°, θmin = 2.0° |
Absorption correction: multi-scan R. H. Blessing, Acta Cryst. 1995 A51, 33-38 | h = −11→9 |
Tmin = 0.900, Tmax = 0.948 | k = −15→15 |
15653 measured reflections | l = −25→25 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.0605P)2 + 0.3891P] where P = (Fo2 + 2Fc2)/3 |
S = 1.14 | (Δ/σ)max < 0.001 |
4791 reflections | Δρmax = 0.28 e Å−3 |
258 parameters | Δρmin = −0.33 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.02 (6) |
C18H20ClNO8 | V = 1933.2 (6) Å3 |
Mr = 413.80 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.5456 (17) Å | µ = 0.24 mm−1 |
b = 11.740 (2) Å | T = 110 K |
c = 19.269 (4) Å | 0.44 × 0.33 × 0.22 mm |
Rigaku Saturn 70 CCD area detector diffractometer | 4791 independent reflections |
Absorption correction: multi-scan R. H. Blessing, Acta Cryst. 1995 A51, 33-38 | 4703 reflections with I > 2σ(I) |
Tmin = 0.900, Tmax = 0.948 | Rint = 0.026 |
15653 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.110 | Δρmax = 0.28 e Å−3 |
S = 1.14 | Δρmin = −0.33 e Å−3 |
4791 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
258 parameters | Absolute structure parameter: −0.02 (6) |
0 restraints |
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 | ||
Cl1 | 0.10461 (5) | 0.09159 (4) | 0.07669 (2) | 0.02513 (11) | |
O5 | 0.24075 (15) | 0.31871 (11) | 0.07482 (8) | 0.0256 (3) | |
O4 | 0.78786 (16) | −0.06498 (11) | 0.11357 (8) | 0.0256 (3) | |
O3 | 0.37426 (15) | −0.07102 (10) | 0.09214 (7) | 0.0207 (3) | |
O6 | 0.77866 (15) | 0.19309 (11) | 0.09915 (7) | 0.0237 (3) | |
O2 | 0.51498 (17) | −0.16627 (11) | −0.01456 (7) | 0.0256 (3) | |
C12 | 0.3000 (2) | 0.12555 (15) | 0.08278 (9) | 0.0203 (3) | |
C11 | 0.3537 (2) | 0.23895 (14) | 0.08133 (9) | 0.0202 (3) | |
C10 | 0.5141 (2) | 0.26543 (14) | 0.08674 (9) | 0.0202 (3) | |
H10 | 0.5477 | 0.3425 | 0.0856 | 0.024* | |
C8 | 0.57096 (19) | 0.06441 (14) | 0.09584 (9) | 0.0189 (3) | |
C7 | 0.6497 (2) | −0.04254 (15) | 0.10602 (9) | 0.0197 (3) | |
C13 | 0.4106 (2) | 0.04154 (14) | 0.08966 (9) | 0.0194 (3) | |
C9 | 0.6231 (2) | 0.17802 (14) | 0.09384 (9) | 0.0192 (3) | |
C16 | 0.2862 (2) | 0.43617 (14) | 0.06938 (11) | 0.0278 (4) | |
H16A | 0.3414 | 0.4591 | 0.1117 | 0.042* | |
H16B | 0.1928 | 0.4836 | 0.0634 | 0.042* | |
H16C | 0.3555 | 0.4459 | 0.0293 | 0.042* | |
C17 | 0.8349 (2) | 0.30797 (15) | 0.10406 (11) | 0.0242 (4) | |
H17A | 0.8043 | 0.3503 | 0.0624 | 0.036* | |
H17B | 0.9492 | 0.3075 | 0.1081 | 0.036* | |
H17C | 0.7895 | 0.3446 | 0.1451 | 0.036* | |
C4 | 0.5174 (2) | −0.13393 (14) | 0.10556 (9) | 0.0202 (3) | |
C3 | 0.5468 (2) | −0.21592 (15) | 0.04676 (10) | 0.0225 (4) | |
C5 | 0.4961 (2) | −0.19527 (16) | 0.17478 (10) | 0.0246 (4) | |
H5 | 0.3955 | −0.2386 | 0.1719 | 0.029* | |
O1 | 0.7042 (3) | −0.45623 (15) | 0.13399 (10) | 0.0563 (6) | |
C2 | 0.6076 (3) | −0.31998 (16) | 0.05644 (10) | 0.0295 (4) | |
H2 | 0.6238 | −0.3681 | 0.0174 | 0.035* | |
C6 | 0.6264 (3) | −0.28207 (16) | 0.18613 (11) | 0.0297 (4) | |
H6A | 0.7256 | −0.2410 | 0.1951 | 0.036* | |
H6B | 0.6018 | −0.3279 | 0.2279 | 0.036* | |
C15 | 0.5478 (3) | −0.23158 (19) | −0.07599 (11) | 0.0344 (5) | |
H15A | 0.6597 | −0.2494 | −0.0778 | 0.052* | |
H15B | 0.5184 | −0.1874 | −0.1171 | 0.052* | |
H15C | 0.4874 | −0.3026 | −0.0749 | 0.052* | |
C14 | 0.4816 (3) | −0.11285 (19) | 0.23569 (10) | 0.0328 (5) | |
H14A | 0.4574 | −0.1556 | 0.2781 | 0.049* | |
H14B | 0.3976 | −0.0582 | 0.2264 | 0.049* | |
H14C | 0.5806 | −0.0719 | 0.2418 | 0.049* | |
C1 | 0.6492 (3) | −0.36114 (17) | 0.12535 (12) | 0.0334 (5) | |
N1 | 0.0925 (3) | 0.60691 (17) | 0.24641 (10) | 0.0380 (4) | |
O7 | 0.0178 (3) | 0.69429 (16) | 0.25471 (10) | 0.0544 (5) | |
C18 | 0.0079 (3) | 0.4970 (2) | 0.24978 (14) | 0.0414 (5) | |
H18A | −0.0070 | 0.4752 | 0.2984 | 0.062* | |
H18B | 0.0690 | 0.4382 | 0.2259 | 0.062* | |
H18C | −0.0943 | 0.5049 | 0.2272 | 0.062* | |
O8 | 0.2333 (3) | 0.60421 (19) | 0.23539 (12) | 0.0596 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.01660 (18) | 0.0255 (2) | 0.0333 (2) | 0.00091 (16) | −0.00179 (17) | −0.00053 (17) |
O5 | 0.0198 (6) | 0.0194 (6) | 0.0376 (7) | 0.0048 (5) | −0.0016 (6) | 0.0023 (6) |
O4 | 0.0173 (6) | 0.0222 (6) | 0.0373 (7) | 0.0031 (5) | −0.0036 (5) | −0.0010 (5) |
O3 | 0.0165 (6) | 0.0161 (5) | 0.0294 (6) | −0.0001 (4) | −0.0005 (5) | 0.0000 (4) |
O6 | 0.0166 (6) | 0.0170 (6) | 0.0374 (7) | −0.0003 (5) | −0.0012 (5) | −0.0023 (5) |
O2 | 0.0289 (7) | 0.0255 (6) | 0.0223 (6) | 0.0002 (6) | −0.0012 (5) | −0.0019 (5) |
C12 | 0.0167 (8) | 0.0215 (8) | 0.0225 (8) | 0.0010 (6) | −0.0017 (6) | 0.0014 (6) |
C11 | 0.0185 (8) | 0.0194 (7) | 0.0228 (8) | 0.0049 (6) | 0.0011 (6) | −0.0001 (6) |
C10 | 0.0204 (8) | 0.0171 (7) | 0.0229 (8) | 0.0004 (6) | 0.0013 (7) | −0.0010 (6) |
C8 | 0.0165 (8) | 0.0181 (7) | 0.0222 (8) | 0.0009 (6) | −0.0021 (6) | −0.0016 (6) |
C7 | 0.0202 (8) | 0.0175 (7) | 0.0213 (8) | 0.0016 (6) | −0.0007 (6) | −0.0009 (6) |
C13 | 0.0205 (8) | 0.0160 (7) | 0.0218 (7) | −0.0003 (6) | 0.0010 (6) | 0.0008 (6) |
C9 | 0.0167 (8) | 0.0177 (7) | 0.0233 (8) | −0.0004 (6) | −0.0005 (6) | −0.0017 (6) |
C16 | 0.0263 (9) | 0.0189 (8) | 0.0382 (10) | 0.0061 (7) | −0.0016 (8) | 0.0024 (7) |
C17 | 0.0198 (8) | 0.0177 (7) | 0.0350 (9) | −0.0014 (6) | −0.0005 (7) | −0.0023 (7) |
C4 | 0.0198 (8) | 0.0166 (7) | 0.0242 (8) | 0.0012 (6) | −0.0004 (7) | −0.0014 (6) |
C3 | 0.0211 (8) | 0.0202 (8) | 0.0261 (8) | −0.0019 (7) | 0.0004 (7) | −0.0007 (7) |
C5 | 0.0251 (9) | 0.0220 (8) | 0.0267 (8) | 0.0005 (7) | 0.0016 (7) | 0.0019 (7) |
O1 | 0.0879 (16) | 0.0271 (8) | 0.0538 (11) | 0.0247 (10) | −0.0044 (11) | 0.0036 (7) |
C2 | 0.0355 (10) | 0.0197 (8) | 0.0333 (9) | 0.0011 (8) | 0.0026 (8) | −0.0048 (7) |
C6 | 0.0357 (11) | 0.0230 (8) | 0.0303 (9) | 0.0025 (8) | −0.0052 (8) | 0.0051 (7) |
C15 | 0.0424 (12) | 0.0367 (10) | 0.0241 (9) | −0.0062 (9) | 0.0032 (9) | −0.0074 (9) |
C14 | 0.0398 (12) | 0.0356 (11) | 0.0232 (9) | 0.0055 (9) | 0.0040 (8) | 0.0006 (8) |
C1 | 0.0400 (12) | 0.0201 (8) | 0.0400 (11) | 0.0070 (8) | −0.0009 (9) | 0.0017 (8) |
N1 | 0.0457 (12) | 0.0394 (10) | 0.0290 (8) | 0.0033 (9) | −0.0066 (8) | 0.0047 (7) |
O7 | 0.0738 (14) | 0.0436 (10) | 0.0457 (10) | 0.0145 (10) | −0.0172 (10) | −0.0040 (8) |
C18 | 0.0397 (13) | 0.0449 (14) | 0.0395 (11) | −0.0027 (10) | −0.0083 (10) | 0.0010 (10) |
O8 | 0.0510 (12) | 0.0610 (12) | 0.0669 (13) | −0.0056 (11) | 0.0095 (10) | 0.0192 (11) |
Cl1—C12 | 1.7208 (18) | C4—C3 | 1.508 (2) |
O5—C11 | 1.351 (2) | C4—C5 | 1.527 (3) |
O5—C16 | 1.437 (2) | C3—C2 | 1.340 (3) |
O4—C7 | 1.218 (2) | C5—C6 | 1.525 (3) |
O3—C13 | 1.3584 (19) | C5—C14 | 1.526 (3) |
O3—C4 | 1.452 (2) | C5—H5 | 1.0000 |
O6—C9 | 1.345 (2) | O1—C1 | 1.223 (3) |
O6—C17 | 1.435 (2) | C2—C1 | 1.457 (3) |
O2—C3 | 1.345 (2) | C2—H2 | 0.9500 |
O2—C15 | 1.438 (2) | C6—C1 | 1.507 (3) |
C12—C13 | 1.372 (2) | C6—H6A | 0.9900 |
C12—C11 | 1.408 (2) | C6—H6B | 0.9900 |
C11—C10 | 1.409 (2) | C15—H15A | 0.9800 |
C10—C9 | 1.393 (2) | C15—H15B | 0.9800 |
C10—H10 | 0.9500 | C15—H15C | 0.9800 |
C8—C13 | 1.401 (2) | C14—H14A | 0.9800 |
C8—C9 | 1.407 (2) | C14—H14B | 0.9800 |
C8—C7 | 1.438 (2) | C14—H14C | 0.9800 |
C7—C4 | 1.559 (3) | N1—O7 | 1.219 (3) |
C16—H16A | 0.9800 | N1—O8 | 1.222 (3) |
C16—H16B | 0.9800 | N1—C18 | 1.480 (3) |
C16—H16C | 0.9800 | C18—H18A | 0.9800 |
C17—H17A | 0.9800 | C18—H18B | 0.9800 |
C17—H17B | 0.9800 | C18—H18C | 0.9800 |
C17—H17C | 0.9800 | ||
C11—O5—C16 | 118.61 (14) | C2—C3—O2 | 126.55 (17) |
C13—O3—C4 | 107.95 (13) | C2—C3—C4 | 122.80 (17) |
C9—O6—C17 | 117.36 (14) | O2—C3—C4 | 110.46 (15) |
C3—O2—C15 | 116.91 (15) | C6—C5—C14 | 111.86 (16) |
C13—C12—C11 | 117.18 (16) | C6—C5—C4 | 110.68 (16) |
C13—C12—Cl1 | 120.55 (13) | C14—C5—C4 | 112.49 (15) |
C11—C12—Cl1 | 122.27 (13) | C6—C5—H5 | 107.2 |
O5—C11—C12 | 115.10 (15) | C14—C5—H5 | 107.2 |
O5—C11—C10 | 123.30 (15) | C4—C5—H5 | 107.2 |
C12—C11—C10 | 121.60 (15) | C3—C2—C1 | 121.58 (18) |
C9—C10—C11 | 119.69 (16) | C3—C2—H2 | 119.2 |
C9—C10—H10 | 120.2 | C1—C2—H2 | 119.2 |
C11—C10—H10 | 120.2 | C1—C6—C5 | 113.23 (17) |
C13—C8—C9 | 119.28 (15) | C1—C6—H6A | 108.9 |
C13—C8—C7 | 107.59 (15) | C5—C6—H6A | 108.9 |
C9—C8—C7 | 133.09 (16) | C1—C6—H6B | 108.9 |
O4—C7—C8 | 131.21 (17) | C5—C6—H6B | 108.9 |
O4—C7—C4 | 123.70 (16) | H6A—C6—H6B | 107.7 |
C8—C7—C4 | 105.10 (14) | O2—C15—H15A | 109.5 |
O3—C13—C12 | 123.02 (16) | O2—C15—H15B | 109.5 |
O3—C13—C8 | 114.02 (15) | H15A—C15—H15B | 109.5 |
C12—C13—C8 | 122.95 (16) | O2—C15—H15C | 109.5 |
O6—C9—C10 | 124.87 (16) | H15A—C15—H15C | 109.5 |
O6—C9—C8 | 115.84 (15) | H15B—C15—H15C | 109.5 |
C10—C9—C8 | 119.29 (16) | C5—C14—H14A | 109.5 |
O5—C16—H16A | 109.5 | C5—C14—H14B | 109.5 |
O5—C16—H16B | 109.5 | H14A—C14—H14B | 109.5 |
H16A—C16—H16B | 109.5 | C5—C14—H14C | 109.5 |
O5—C16—H16C | 109.5 | H14A—C14—H14C | 109.5 |
H16A—C16—H16C | 109.5 | H14B—C14—H14C | 109.5 |
H16B—C16—H16C | 109.5 | O1—C1—C2 | 121.4 (2) |
O6—C17—H17A | 109.5 | O1—C1—C6 | 120.4 (2) |
O6—C17—H17B | 109.5 | C2—C1—C6 | 118.19 (17) |
H17A—C17—H17B | 109.5 | O7—N1—O8 | 124.1 (3) |
O6—C17—H17C | 109.5 | O7—N1—C18 | 118.1 (2) |
H17A—C17—H17C | 109.5 | O8—N1—C18 | 117.8 (2) |
H17B—C17—H17C | 109.5 | N1—C18—H18A | 109.5 |
O3—C4—C3 | 109.35 (14) | N1—C18—H18B | 109.5 |
O3—C4—C5 | 107.14 (15) | H18A—C18—H18B | 109.5 |
C3—C4—C5 | 112.04 (14) | N1—C18—H18C | 109.5 |
O3—C4—C7 | 105.20 (13) | H18A—C18—H18C | 109.5 |
C3—C4—C7 | 108.83 (15) | H18B—C18—H18C | 109.5 |
C5—C4—C7 | 113.98 (15) |
C36H39Cl2NO14 | F(000) = 1632 |
Mr = 780.58 | Dx = 1.437 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 9491 reflections |
a = 8.6852 (17) Å | θ = 2.0–31.0° |
b = 15.047 (3) Å | µ = 0.25 mm−1 |
c = 27.605 (6) Å | T = 163 K |
V = 3607.6 (13) Å3 | Block, colorless |
Z = 4 | 0.33 × 0.33 × 0.22 mm |
Rigaku Saturn 70 CCD area detector diffractometer | 8492 independent reflections |
Radiation source: fine-focus sealed tube | 7628 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ω scans | θmax = 28.3°, θmin = 1.5° |
Absorption correction: multi-scan R. H. Blessing, Acta Cryst. 1995 A51, 33-38 | h = −10→11 |
Tmin = 0.922, Tmax = 0.947 | k = −13→20 |
15583 measured reflections | l = −16→36 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.043P)2 + 0.9983P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
8492 reflections | Δρmax = 0.21 e Å−3 |
487 parameters | Δρmin = −0.35 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (5) |
C36H39Cl2NO14 | V = 3607.6 (13) Å3 |
Mr = 780.58 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.6852 (17) Å | µ = 0.25 mm−1 |
b = 15.047 (3) Å | T = 163 K |
c = 27.605 (6) Å | 0.33 × 0.33 × 0.22 mm |
Rigaku Saturn 70 CCD area detector diffractometer | 8492 independent reflections |
Absorption correction: multi-scan R. H. Blessing, Acta Cryst. 1995 A51, 33-38 | 7628 reflections with I > 2σ(I) |
Tmin = 0.922, Tmax = 0.947 | Rint = 0.029 |
15583 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.117 | Δρmax = 0.21 e Å−3 |
S = 1.09 | Δρmin = −0.35 e Å−3 |
8492 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
487 parameters | Absolute structure parameter: 0.01 (5) |
0 restraints |
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 | ||
Cl2A | 0.25466 (7) | 0.93344 (5) | 0.79617 (2) | 0.02999 (14) | |
O6A | 0.91789 (19) | 0.95750 (13) | 0.84193 (7) | 0.0298 (4) | |
O4A | 0.9341 (2) | 0.85951 (14) | 0.74378 (7) | 0.0329 (4) | |
O2A | 0.6258 (2) | 0.95824 (13) | 0.67598 (7) | 0.0304 (4) | |
O3A | 0.52424 (19) | 0.85135 (12) | 0.74298 (6) | 0.0254 (4) | |
O5A | 0.3861 (2) | 1.02654 (13) | 0.87787 (7) | 0.0310 (4) | |
C10A | 0.6554 (3) | 0.99334 (18) | 0.86334 (10) | 0.0275 (5) | |
H10A | 0.6866 | 1.0254 | 0.8913 | 0.033* | |
C12A | 0.4471 (3) | 0.93905 (19) | 0.81133 (9) | 0.0269 (5) | |
C8A | 0.7160 (3) | 0.90503 (17) | 0.79335 (9) | 0.0247 (5) | |
C13A | 0.5581 (3) | 0.89865 (17) | 0.78322 (9) | 0.0237 (5) | |
C11A | 0.4983 (3) | 0.98695 (18) | 0.85148 (10) | 0.0267 (5) | |
C9A | 0.7641 (3) | 0.95289 (17) | 0.83424 (9) | 0.0253 (5) | |
O1A | 0.8484 (2) | 0.71295 (15) | 0.59465 (8) | 0.0429 (5) | |
C14A | 0.6835 (4) | 0.6777 (2) | 0.76273 (11) | 0.0377 (7) | |
H14E | 0.7837 | 0.6905 | 0.7774 | 0.057* | |
H14D | 0.6733 | 0.6134 | 0.7577 | 0.057* | |
H14F | 0.6013 | 0.6983 | 0.7843 | 0.057* | |
C2A | 0.7342 (3) | 0.8368 (2) | 0.63125 (10) | 0.0313 (6) | |
H2A | 0.7348 | 0.8695 | 0.6018 | 0.038* | |
C3A | 0.6765 (3) | 0.87440 (19) | 0.67148 (10) | 0.0273 (5) | |
C1A | 0.7960 (3) | 0.7466 (2) | 0.63186 (11) | 0.0317 (6) | |
C7A | 0.7968 (3) | 0.86436 (18) | 0.75331 (9) | 0.0255 (5) | |
C17A | 0.9707 (3) | 1.0122 (2) | 0.88150 (10) | 0.0338 (6) | |
H17D | 0.9358 | 1.0734 | 0.8766 | 0.051* | |
H17F | 1.0834 | 1.0108 | 0.8828 | 0.051* | |
H17E | 0.9287 | 0.9894 | 0.9120 | 0.051* | |
C5A | 0.6711 (3) | 0.72549 (18) | 0.71399 (10) | 0.0281 (5) | |
H5A | 0.5716 | 0.7073 | 0.6987 | 0.034* | |
C4A | 0.6685 (3) | 0.82677 (18) | 0.71964 (9) | 0.0244 (5) | |
C16A | 0.4312 (3) | 1.0837 (2) | 0.91734 (10) | 0.0335 (6) | |
H16E | 0.4934 | 1.0498 | 0.9405 | 0.050* | |
H16D | 0.3390 | 1.1065 | 0.9336 | 0.050* | |
H16F | 0.4917 | 1.1335 | 0.9047 | 0.050* | |
C15A | 0.6373 (4) | 1.0143 (2) | 0.63369 (11) | 0.0387 (7) | |
H15E | 0.7458 | 1.0218 | 0.6249 | 0.058* | |
H15F | 0.5919 | 1.0725 | 0.6408 | 0.058* | |
H15D | 0.5819 | 0.9867 | 0.6067 | 0.058* | |
C6A | 0.8011 (3) | 0.6985 (2) | 0.67950 (10) | 0.0331 (6) | |
H6AA | 0.9012 | 0.7106 | 0.6953 | 0.040* | |
H6AB | 0.7947 | 0.6338 | 0.6734 | 0.040* | |
Cl1 | 1.30892 (7) | 0.55221 (5) | 0.98757 (3) | 0.03578 (17) | |
O4 | 0.6228 (2) | 0.46365 (13) | 0.95249 (7) | 0.0323 (4) | |
O5 | 1.1873 (2) | 0.68532 (14) | 1.05221 (7) | 0.0349 (5) | |
C7 | 0.7606 (3) | 0.47843 (17) | 0.95503 (9) | 0.0262 (5) | |
O3 | 1.03089 (19) | 0.46104 (13) | 0.94255 (7) | 0.0275 (4) | |
O6 | 0.6493 (2) | 0.62105 (14) | 1.02196 (8) | 0.0332 (4) | |
O2 | 0.9426 (2) | 0.31530 (14) | 0.98710 (7) | 0.0327 (4) | |
C2 | 0.8043 (3) | 0.26401 (19) | 0.91760 (10) | 0.0296 (6) | |
H2 | 0.7977 | 0.2056 | 0.9305 | 0.035* | |
C10 | 0.9148 (3) | 0.65794 (19) | 1.03977 (10) | 0.0285 (5) | |
H10 | 0.8866 | 0.7021 | 1.0627 | 0.034* | |
O1 | 0.6744 (3) | 0.22285 (15) | 0.84724 (9) | 0.0469 (6) | |
C12 | 1.1166 (3) | 0.57592 (19) | 0.99705 (10) | 0.0286 (6) | |
C9 | 0.8019 (3) | 0.61001 (18) | 1.01572 (10) | 0.0273 (5) | |
C13 | 1.0020 (3) | 0.52884 (18) | 0.97396 (9) | 0.0249 (5) | |
C8 | 0.8456 (3) | 0.54368 (18) | 0.98230 (10) | 0.0270 (5) | |
C11 | 1.0707 (3) | 0.64114 (19) | 1.03028 (10) | 0.0295 (6) | |
C1 | 0.7369 (3) | 0.28192 (19) | 0.87093 (10) | 0.0321 (6) | |
C6 | 0.7398 (3) | 0.37619 (19) | 0.85215 (10) | 0.0311 (6) | |
H6A | 0.6418 | 0.4057 | 0.8608 | 0.037* | |
H6B | 0.7468 | 0.3748 | 0.8164 | 0.037* | |
C17 | 0.6005 (3) | 0.6832 (2) | 1.05876 (11) | 0.0358 (7) | |
H17A | 0.6406 | 0.6643 | 1.0903 | 0.054* | |
H17B | 0.4878 | 0.6849 | 1.0599 | 0.054* | |
H17C | 0.6400 | 0.7425 | 1.0510 | 0.054* | |
C3 | 0.8767 (3) | 0.32747 (18) | 0.94364 (10) | 0.0263 (5) | |
C5 | 0.8733 (3) | 0.43124 (19) | 0.87197 (10) | 0.0279 (5) | |
H6 | 0.9705 | 0.4059 | 0.8582 | 0.033* | |
C4 | 0.8834 (3) | 0.42301 (18) | 0.92743 (9) | 0.0257 (5) | |
C14 | 0.8626 (4) | 0.5272 (2) | 0.85524 (11) | 0.0398 (7) | |
H14A | 0.8693 | 0.5295 | 0.8198 | 0.060* | |
H14B | 0.9474 | 0.5615 | 0.8694 | 0.060* | |
H14C | 0.7641 | 0.5525 | 0.8657 | 0.060* | |
C15 | 0.9402 (4) | 0.2258 (2) | 1.00673 (11) | 0.0404 (7) | |
H15A | 0.8333 | 0.2067 | 1.0112 | 0.061* | |
H15B | 0.9936 | 0.2250 | 1.0380 | 0.061* | |
H15C | 0.9920 | 0.1853 | 0.9842 | 0.061* | |
C16 | 1.1494 (4) | 0.7501 (2) | 1.08890 (13) | 0.0458 (8) | |
H16A | 1.0894 | 0.7983 | 1.0743 | 0.069* | |
H16B | 1.2445 | 0.7743 | 1.1028 | 0.069* | |
H16C | 1.0888 | 0.7217 | 1.1145 | 0.069* | |
N1 | 0.2014 (3) | 0.71881 (17) | 0.82048 (10) | 0.0400 (6) | |
O8 | 0.3215 (3) | 0.73025 (17) | 0.84314 (9) | 0.0544 (7) | |
C18 | 0.2089 (3) | 0.71292 (19) | 0.76654 (10) | 0.0332 (6) | |
H18A | 0.3097 | 0.7353 | 0.7550 | 0.040* | |
H18B | 0.1269 | 0.7500 | 0.7520 | 0.040* | |
O7 | 0.0760 (3) | 0.71093 (19) | 0.83980 (10) | 0.0667 (8) | |
C19 | 0.1886 (5) | 0.6183 (2) | 0.75147 (13) | 0.0556 (10) | |
H19A | 0.2697 | 0.5818 | 0.7661 | 0.083* | |
H19B | 0.1950 | 0.6140 | 0.7161 | 0.083* | |
H19C | 0.0877 | 0.5969 | 0.7623 | 0.083* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl2A | 0.0218 (3) | 0.0329 (3) | 0.0352 (3) | 0.0015 (3) | −0.0007 (3) | −0.0039 (3) |
O6A | 0.0205 (8) | 0.0384 (11) | 0.0304 (10) | −0.0018 (8) | −0.0028 (7) | −0.0076 (9) |
O4A | 0.0222 (9) | 0.0424 (12) | 0.0341 (10) | −0.0003 (8) | 0.0005 (8) | −0.0058 (9) |
O2A | 0.0363 (10) | 0.0281 (10) | 0.0269 (9) | 0.0021 (8) | −0.0019 (8) | 0.0033 (8) |
O3A | 0.0230 (8) | 0.0296 (10) | 0.0236 (9) | −0.0002 (7) | 0.0007 (7) | −0.0053 (8) |
O5A | 0.0269 (9) | 0.0363 (11) | 0.0299 (10) | 0.0044 (8) | 0.0016 (8) | −0.0072 (8) |
C10A | 0.0262 (12) | 0.0298 (13) | 0.0264 (12) | 0.0022 (10) | −0.0001 (10) | −0.0030 (11) |
C12A | 0.0226 (11) | 0.0298 (14) | 0.0284 (12) | 0.0026 (11) | 0.0004 (10) | −0.0011 (11) |
C8A | 0.0260 (12) | 0.0240 (12) | 0.0242 (11) | −0.0011 (10) | −0.0011 (10) | −0.0016 (10) |
C13A | 0.0241 (12) | 0.0240 (12) | 0.0229 (12) | 0.0000 (10) | −0.0008 (10) | −0.0014 (10) |
C11A | 0.0249 (12) | 0.0279 (13) | 0.0273 (13) | 0.0040 (10) | 0.0028 (10) | −0.0006 (11) |
C9A | 0.0213 (11) | 0.0267 (12) | 0.0279 (12) | −0.0009 (10) | −0.0011 (10) | 0.0002 (10) |
O1A | 0.0397 (11) | 0.0500 (14) | 0.0388 (12) | −0.0068 (10) | 0.0130 (10) | −0.0160 (11) |
C14A | 0.0430 (16) | 0.0356 (16) | 0.0346 (15) | 0.0039 (14) | −0.0011 (14) | 0.0000 (13) |
C2A | 0.0316 (14) | 0.0382 (15) | 0.0242 (12) | −0.0066 (12) | 0.0024 (11) | −0.0013 (11) |
C3A | 0.0258 (12) | 0.0294 (14) | 0.0267 (12) | −0.0013 (11) | −0.0036 (11) | −0.0022 (11) |
C1A | 0.0222 (12) | 0.0394 (15) | 0.0336 (14) | −0.0067 (11) | 0.0049 (11) | −0.0102 (12) |
C7A | 0.0252 (12) | 0.0255 (12) | 0.0258 (12) | 0.0011 (10) | −0.0005 (10) | −0.0020 (10) |
C17A | 0.0268 (13) | 0.0448 (17) | 0.0299 (14) | −0.0068 (12) | −0.0025 (11) | −0.0087 (13) |
C5A | 0.0280 (13) | 0.0270 (13) | 0.0292 (13) | 0.0017 (11) | 0.0024 (11) | −0.0022 (11) |
C4A | 0.0210 (11) | 0.0281 (13) | 0.0242 (12) | 0.0024 (10) | 0.0011 (10) | −0.0030 (10) |
C16A | 0.0374 (15) | 0.0359 (15) | 0.0271 (13) | 0.0044 (13) | −0.0002 (12) | −0.0074 (12) |
C15A | 0.0433 (16) | 0.0368 (16) | 0.0360 (16) | −0.0091 (13) | −0.0056 (13) | 0.0095 (13) |
C6A | 0.0281 (13) | 0.0374 (15) | 0.0337 (14) | 0.0030 (12) | 0.0014 (12) | −0.0066 (13) |
Cl1 | 0.0221 (3) | 0.0506 (4) | 0.0346 (3) | −0.0017 (3) | −0.0003 (3) | −0.0093 (3) |
O4 | 0.0220 (9) | 0.0375 (11) | 0.0374 (11) | −0.0007 (8) | −0.0023 (8) | −0.0063 (9) |
O5 | 0.0287 (9) | 0.0398 (11) | 0.0363 (11) | −0.0086 (9) | 0.0003 (9) | −0.0132 (9) |
C7 | 0.0233 (11) | 0.0275 (12) | 0.0279 (12) | 0.0014 (10) | −0.0027 (10) | 0.0018 (10) |
O3 | 0.0216 (8) | 0.0325 (10) | 0.0284 (9) | −0.0019 (7) | −0.0011 (7) | −0.0081 (8) |
O6 | 0.0261 (9) | 0.0360 (11) | 0.0375 (11) | 0.0028 (8) | 0.0027 (8) | −0.0116 (9) |
O2 | 0.0398 (11) | 0.0325 (11) | 0.0259 (9) | 0.0020 (9) | −0.0062 (9) | −0.0003 (9) |
C2 | 0.0271 (12) | 0.0322 (14) | 0.0295 (13) | −0.0013 (11) | −0.0005 (11) | −0.0028 (11) |
C10 | 0.0268 (12) | 0.0308 (14) | 0.0279 (13) | 0.0007 (11) | 0.0003 (11) | −0.0050 (11) |
O1 | 0.0562 (14) | 0.0404 (12) | 0.0441 (13) | −0.0126 (11) | −0.0143 (11) | −0.0071 (11) |
C12 | 0.0232 (12) | 0.0347 (14) | 0.0278 (13) | −0.0030 (11) | 0.0002 (10) | −0.0032 (11) |
C9 | 0.0275 (12) | 0.0259 (13) | 0.0285 (12) | 0.0012 (10) | −0.0003 (11) | −0.0005 (11) |
C13 | 0.0243 (12) | 0.0261 (13) | 0.0244 (12) | 0.0000 (10) | −0.0006 (10) | −0.0040 (10) |
C8 | 0.0231 (12) | 0.0315 (14) | 0.0265 (12) | 0.0011 (10) | −0.0036 (10) | −0.0012 (11) |
C11 | 0.0273 (13) | 0.0316 (14) | 0.0297 (13) | −0.0073 (11) | −0.0020 (11) | −0.0027 (12) |
C1 | 0.0318 (14) | 0.0334 (14) | 0.0312 (14) | −0.0019 (12) | 0.0013 (12) | −0.0060 (12) |
C6 | 0.0306 (13) | 0.0332 (14) | 0.0295 (13) | 0.0019 (12) | −0.0074 (12) | −0.0038 (11) |
C17 | 0.0309 (14) | 0.0374 (16) | 0.0392 (16) | 0.0056 (12) | 0.0045 (13) | −0.0140 (14) |
C3 | 0.0247 (12) | 0.0300 (13) | 0.0242 (12) | 0.0032 (10) | −0.0007 (10) | 0.0003 (11) |
C5 | 0.0267 (12) | 0.0314 (13) | 0.0255 (12) | 0.0006 (11) | −0.0012 (10) | 0.0003 (11) |
C4 | 0.0225 (11) | 0.0284 (13) | 0.0262 (12) | −0.0026 (10) | −0.0033 (10) | −0.0048 (11) |
C14 | 0.0483 (17) | 0.0378 (16) | 0.0333 (15) | −0.0023 (14) | 0.0019 (13) | 0.0050 (13) |
C15 | 0.0520 (18) | 0.0369 (17) | 0.0323 (15) | 0.0073 (14) | −0.0039 (14) | 0.0056 (13) |
C16 | 0.0429 (17) | 0.0476 (19) | 0.0468 (19) | −0.0098 (15) | 0.0003 (15) | −0.0243 (16) |
N1 | 0.0523 (16) | 0.0303 (13) | 0.0373 (14) | −0.0088 (12) | 0.0004 (13) | −0.0023 (11) |
O8 | 0.0690 (16) | 0.0469 (14) | 0.0472 (14) | 0.0061 (13) | −0.0217 (13) | −0.0057 (12) |
C18 | 0.0381 (15) | 0.0292 (14) | 0.0325 (14) | −0.0003 (12) | −0.0001 (12) | 0.0016 (12) |
O7 | 0.0750 (18) | 0.0679 (19) | 0.0573 (17) | −0.0324 (15) | 0.0252 (15) | −0.0161 (15) |
C19 | 0.096 (3) | 0.0287 (16) | 0.0421 (18) | −0.0017 (18) | −0.003 (2) | −0.0030 (14) |
Cl2A—C12A | 1.725 (3) | C7—C4 | 1.554 (4) |
O6A—C9A | 1.355 (3) | O3—C13 | 1.362 (3) |
O6A—C17A | 1.442 (3) | O3—C4 | 1.464 (3) |
O4A—C7A | 1.223 (3) | O6—C9 | 1.347 (3) |
O2A—C3A | 1.342 (3) | O6—C17 | 1.444 (3) |
O2A—C15A | 1.444 (3) | O2—C3 | 1.342 (3) |
O3A—C13A | 1.352 (3) | O2—C15 | 1.452 (4) |
O3A—C4A | 1.457 (3) | C2—C3 | 1.351 (4) |
O5A—C11A | 1.355 (3) | C2—C1 | 1.441 (4) |
O5A—C16A | 1.442 (3) | C2—H2 | 0.9500 |
C10A—C9A | 1.381 (4) | C10—C9 | 1.387 (4) |
C10A—C11A | 1.406 (3) | C10—C11 | 1.402 (4) |
C10A—H10A | 0.9500 | C10—H10 | 0.9500 |
C12A—C13A | 1.379 (4) | O1—C1 | 1.230 (3) |
C12A—C11A | 1.395 (4) | C12—C13 | 1.378 (4) |
C8A—C9A | 1.402 (3) | C12—C11 | 1.401 (4) |
C8A—C13A | 1.403 (3) | C9—C8 | 1.411 (4) |
C8A—C7A | 1.445 (4) | C13—C8 | 1.396 (3) |
O1A—C1A | 1.233 (3) | C1—C6 | 1.511 (4) |
C14A—C5A | 1.530 (4) | C6—C5 | 1.527 (4) |
C14A—H14E | 0.9800 | C6—H6A | 0.9900 |
C14A—H14D | 0.9800 | C6—H6B | 0.9900 |
C14A—H14F | 0.9800 | C17—H17A | 0.9800 |
C2A—C3A | 1.344 (4) | C17—H17B | 0.9800 |
C2A—C1A | 1.459 (4) | C17—H17C | 0.9800 |
C2A—H2A | 0.9500 | C3—C4 | 1.507 (4) |
C3A—C4A | 1.512 (4) | C5—C14 | 1.519 (4) |
C1A—C6A | 1.502 (4) | C5—C4 | 1.539 (4) |
C7A—C4A | 1.557 (4) | C5—H6 | 1.0000 |
C17A—H17D | 0.9800 | C14—H14A | 0.9800 |
C17A—H17F | 0.9800 | C14—H14B | 0.9800 |
C17A—H17E | 0.9800 | C14—H14C | 0.9800 |
C5A—C6A | 1.532 (4) | C15—H15A | 0.9800 |
C5A—C4A | 1.532 (4) | C15—H15B | 0.9800 |
C5A—H5A | 1.0000 | C15—H15C | 0.9800 |
C16A—H16E | 0.9800 | C16—H16A | 0.9800 |
C16A—H16D | 0.9800 | C16—H16B | 0.9800 |
C16A—H16F | 0.9800 | C16—H16C | 0.9800 |
C15A—H15E | 0.9800 | N1—O7 | 1.218 (4) |
C15A—H15F | 0.9800 | N1—O8 | 1.228 (4) |
C15A—H15D | 0.9800 | N1—C18 | 1.493 (4) |
C6A—H6AA | 0.9900 | C18—C19 | 1.494 (4) |
C6A—H6AB | 0.9900 | C18—H18A | 0.9900 |
Cl1—C12 | 1.728 (3) | C18—H18B | 0.9900 |
O4—C7 | 1.219 (3) | C19—H19A | 0.9800 |
O5—C11 | 1.354 (3) | C19—H19B | 0.9800 |
O5—C16 | 1.444 (4) | C19—H19C | 0.9800 |
C7—C8 | 1.441 (4) | ||
C9A—O6A—C17A | 117.5 (2) | C3—C2—H2 | 118.9 |
C3A—O2A—C15A | 116.9 (2) | C1—C2—H2 | 118.9 |
C13A—O3A—C4A | 108.06 (19) | C9—C10—C11 | 120.0 (3) |
C11A—O5A—C16A | 118.2 (2) | C9—C10—H10 | 120.0 |
C9A—C10A—C11A | 119.8 (3) | C11—C10—H10 | 120.0 |
C9A—C10A—H10A | 120.1 | C13—C12—C11 | 117.2 (2) |
C11A—C10A—H10A | 120.1 | C13—C12—Cl1 | 121.5 (2) |
C13A—C12A—C11A | 116.9 (2) | C11—C12—Cl1 | 121.2 (2) |
C13A—C12A—Cl2A | 121.3 (2) | O6—C9—C10 | 124.8 (2) |
C11A—C12A—Cl2A | 121.8 (2) | O6—C9—C8 | 115.8 (2) |
C9A—C8A—C13A | 119.1 (2) | C10—C9—C8 | 119.4 (2) |
C9A—C8A—C7A | 133.5 (2) | O3—C13—C12 | 123.1 (2) |
C13A—C8A—C7A | 107.1 (2) | O3—C13—C8 | 113.8 (2) |
O3A—C13A—C12A | 122.9 (2) | C12—C13—C8 | 123.0 (2) |
O3A—C13A—C8A | 114.3 (2) | C13—C8—C9 | 118.8 (2) |
C12A—C13A—C8A | 122.7 (2) | C13—C8—C7 | 107.7 (2) |
O5A—C11A—C12A | 115.2 (2) | C9—C8—C7 | 133.3 (2) |
O5A—C11A—C10A | 122.9 (2) | O5—C11—C12 | 115.1 (2) |
C12A—C11A—C10A | 122.0 (2) | O5—C11—C10 | 123.4 (3) |
O6A—C9A—C10A | 124.1 (2) | C12—C11—C10 | 121.5 (2) |
O6A—C9A—C8A | 116.5 (2) | O1—C1—C2 | 121.3 (3) |
C10A—C9A—C8A | 119.4 (2) | O1—C1—C6 | 120.2 (3) |
C5A—C14A—H14E | 109.5 | C2—C1—C6 | 118.4 (2) |
C5A—C14A—H14D | 109.5 | C1—C6—C5 | 113.5 (2) |
H14E—C14A—H14D | 109.5 | C1—C6—H6A | 108.9 |
C5A—C14A—H14F | 109.5 | C5—C6—H6A | 108.9 |
H14E—C14A—H14F | 109.5 | C1—C6—H6B | 108.9 |
H14D—C14A—H14F | 109.5 | C5—C6—H6B | 108.9 |
C3A—C2A—C1A | 121.3 (3) | H6A—C6—H6B | 107.7 |
C3A—C2A—H2A | 119.3 | O6—C17—H17A | 109.5 |
C1A—C2A—H2A | 119.3 | O6—C17—H17B | 109.5 |
O2A—C3A—C2A | 126.5 (3) | H17A—C17—H17B | 109.5 |
O2A—C3A—C4A | 110.4 (2) | O6—C17—H17C | 109.5 |
C2A—C3A—C4A | 123.0 (3) | H17A—C17—H17C | 109.5 |
O1A—C1A—C2A | 120.6 (3) | H17B—C17—H17C | 109.5 |
O1A—C1A—C6A | 121.4 (3) | O2—C3—C2 | 125.3 (3) |
C2A—C1A—C6A | 118.0 (2) | O2—C3—C4 | 112.3 (2) |
O4A—C7A—C8A | 131.6 (3) | C2—C3—C4 | 122.3 (2) |
O4A—C7A—C4A | 123.2 (2) | C14—C5—C6 | 111.1 (2) |
C8A—C7A—C4A | 105.2 (2) | C14—C5—C4 | 112.5 (2) |
O6A—C17A—H17D | 109.5 | C6—C5—C4 | 110.9 (2) |
O6A—C17A—H17F | 109.5 | C14—C5—H6 | 107.4 |
H17D—C17A—H17F | 109.5 | C6—C5—H6 | 107.4 |
O6A—C17A—H17E | 109.5 | C4—C5—H6 | 107.4 |
H17D—C17A—H17E | 109.5 | O3—C4—C3 | 108.8 (2) |
H17F—C17A—H17E | 109.5 | O3—C4—C5 | 107.6 (2) |
C14A—C5A—C6A | 111.7 (2) | C3—C4—C5 | 111.7 (2) |
C14A—C5A—C4A | 112.3 (2) | O3—C4—C7 | 104.5 (2) |
C6A—C5A—C4A | 109.7 (2) | C3—C4—C7 | 109.9 (2) |
C14A—C5A—H5A | 107.6 | C5—C4—C7 | 113.9 (2) |
C6A—C5A—H5A | 107.6 | C5—C14—H14A | 109.5 |
C4A—C5A—H5A | 107.6 | C5—C14—H14B | 109.5 |
O3A—C4A—C3A | 107.9 (2) | H14A—C14—H14B | 109.5 |
O3A—C4A—C5A | 108.1 (2) | C5—C14—H14C | 109.5 |
C3A—C4A—C5A | 112.4 (2) | H14A—C14—H14C | 109.5 |
O3A—C4A—C7A | 105.0 (2) | H14B—C14—H14C | 109.5 |
C3A—C4A—C7A | 108.7 (2) | O2—C15—H15A | 109.5 |
C5A—C4A—C7A | 114.3 (2) | O2—C15—H15B | 109.5 |
O5A—C16A—H16E | 109.5 | H15A—C15—H15B | 109.5 |
O5A—C16A—H16D | 109.5 | O2—C15—H15C | 109.5 |
H16E—C16A—H16D | 109.5 | H15A—C15—H15C | 109.5 |
O5A—C16A—H16F | 109.5 | H15B—C15—H15C | 109.5 |
H16E—C16A—H16F | 109.5 | O5—C16—H16A | 109.5 |
H16D—C16A—H16F | 109.5 | O5—C16—H16B | 109.5 |
O2A—C15A—H15E | 109.5 | H16A—C16—H16B | 109.5 |
O2A—C15A—H15F | 109.5 | O5—C16—H16C | 109.5 |
H15E—C15A—H15F | 109.5 | H16A—C16—H16C | 109.5 |
O2A—C15A—H15D | 109.5 | H16B—C16—H16C | 109.5 |
H15E—C15A—H15D | 109.5 | O7—N1—O8 | 123.3 (3) |
H15F—C15A—H15D | 109.5 | O7—N1—C18 | 118.0 (3) |
C1A—C6A—C5A | 113.2 (2) | O8—N1—C18 | 118.6 (3) |
C1A—C6A—H6AA | 108.9 | N1—C18—C19 | 109.2 (3) |
C5A—C6A—H6AA | 108.9 | N1—C18—H18A | 109.8 |
C1A—C6A—H6AB | 108.9 | C19—C18—H18A | 109.8 |
C5A—C6A—H6AB | 108.9 | N1—C18—H18B | 109.8 |
H6AA—C6A—H6AB | 107.7 | C19—C18—H18B | 109.8 |
C11—O5—C16 | 118.4 (2) | H18A—C18—H18B | 108.3 |
O4—C7—C8 | 131.1 (3) | C18—C19—H19A | 109.5 |
O4—C7—C4 | 123.2 (2) | C18—C19—H19B | 109.5 |
C8—C7—C4 | 105.7 (2) | H19A—C19—H19B | 109.5 |
C13—O3—C4 | 108.25 (19) | C18—C19—H19C | 109.5 |
C9—O6—C17 | 117.3 (2) | H19A—C19—H19C | 109.5 |
C3—O2—C15 | 117.0 (2) | H19B—C19—H19C | 109.5 |
C3—C2—C1 | 122.2 (3) |
C19H22ClNO8 | F(000) = 896 |
Mr = 427.83 | Dx = 1.432 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 2981 reflections |
a = 21.931 (4) Å | θ = 2.1–31.0° |
b = 8.6541 (17) Å | µ = 0.24 mm−1 |
c = 11.797 (2) Å | T = 110 K |
β = 117.57 (3)° | Block, colorless |
V = 1984.7 (8) Å3 | 0.44 × 0.44 × 0.44 mm |
Z = 4 |
Rigaku Saturn 70 CCD area detector diffractometer | 4634 independent reflections |
Radiation source: fine-focus sealed tube | 4497 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
ω scans | θmax = 28.3°, θmin = 2.0° |
Absorption correction: multi-scan R. H. Blessing, Acta Cryst. 1995 A51, 33-38 | h = −29→26 |
Tmin = 0.910, Tmax = 0.910 | k = −11→11 |
7580 measured reflections | l = −15→15 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.0696P)2 + 1.1066P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.119 | (Δ/σ)max < 0.001 |
S = 1.09 | Δρmax = 0.43 e Å−3 |
4634 reflections | Δρmin = −0.33 e Å−3 |
222 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0027 (6) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.03 (6) |
C19H22ClNO8 | V = 1984.7 (8) Å3 |
Mr = 427.83 | Z = 4 |
Monoclinic, C2 | Mo Kα radiation |
a = 21.931 (4) Å | µ = 0.24 mm−1 |
b = 8.6541 (17) Å | T = 110 K |
c = 11.797 (2) Å | 0.44 × 0.44 × 0.44 mm |
β = 117.57 (3)° |
Rigaku Saturn 70 CCD area detector diffractometer | 4634 independent reflections |
Absorption correction: multi-scan R. H. Blessing, Acta Cryst. 1995 A51, 33-38 | 4497 reflections with I > 2σ(I) |
Tmin = 0.910, Tmax = 0.910 | Rint = 0.016 |
7580 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.119 | Δρmax = 0.43 e Å−3 |
S = 1.09 | Δρmin = −0.33 e Å−3 |
4634 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
222 parameters | Absolute structure parameter: 0.03 (6) |
1 restraint |
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 | ||
Cl1 | 0.82785 (2) | −0.35650 (6) | 0.90574 (4) | 0.02756 (12) | |
O8 | 0.85329 (8) | 0.32212 (18) | 0.77080 (14) | 0.0278 (3) | |
O7 | 0.83918 (8) | −0.08887 (17) | 0.75312 (13) | 0.0246 (3) | |
O6 | 0.72964 (8) | 0.05097 (19) | 0.57020 (14) | 0.0301 (3) | |
C10 | 0.83478 (10) | 0.0471 (2) | 1.08388 (18) | 0.0229 (4) | |
H10 | 0.8336 | 0.0799 | 1.1597 | 0.027* | |
O9 | 0.82446 (8) | −0.22128 (17) | 1.12859 (14) | 0.0282 (3) | |
C9 | 0.84110 (9) | 0.1554 (2) | 1.00308 (17) | 0.0220 (4) | |
C11 | 0.83018 (10) | −0.1099 (2) | 1.05369 (18) | 0.0218 (4) | |
C13 | 0.83719 (10) | −0.0521 (2) | 0.86316 (18) | 0.0211 (4) | |
O10 | 0.84719 (8) | 0.31013 (16) | 1.02326 (13) | 0.0241 (3) | |
C7 | 0.84864 (10) | 0.1843 (2) | 0.78915 (18) | 0.0223 (4) | |
C12 | 0.83167 (10) | −0.1632 (2) | 0.94278 (19) | 0.0221 (4) | |
C4 | 0.84967 (10) | 0.0541 (2) | 0.69879 (18) | 0.0231 (4) | |
C3 | 0.78913 (11) | 0.0771 (2) | 0.56805 (19) | 0.0253 (4) | |
C5 | 0.91826 (11) | 0.0387 (3) | 0.69502 (19) | 0.0283 (4) | |
H5 | 0.9181 | −0.0642 | 0.6564 | 0.034* | |
C17 | 0.85378 (12) | 0.3655 (3) | 1.14331 (18) | 0.0280 (4) | |
H17A | 0.8928 | 0.3143 | 1.2136 | 0.042* | |
H17B | 0.8115 | 0.3426 | 1.1490 | 0.042* | |
H17C | 0.8615 | 0.4775 | 1.1491 | 0.042* | |
C8 | 0.84141 (10) | 0.1051 (2) | 0.89023 (18) | 0.0236 (4) | |
C16 | 0.81688 (13) | −0.1753 (3) | 1.2390 (2) | 0.0334 (5) | |
H16A | 0.7766 | −0.1081 | 1.2120 | 0.050* | |
H16B | 0.8581 | −0.1194 | 1.2989 | 0.050* | |
H16C | 0.8108 | −0.2674 | 1.2811 | 0.050* | |
O5 | 0.87189 (12) | 0.1927 (3) | 0.38399 (19) | 0.0582 (6) | |
C2 | 0.79711 (12) | 0.1264 (3) | 0.46686 (19) | 0.0343 (5) | |
H2 | 0.7575 | 0.1390 | 0.3865 | 0.041* | |
C14 | 0.98022 (12) | 0.0409 (3) | 0.8294 (2) | 0.0393 (5) | |
H14A | 0.9882 | 0.1467 | 0.8628 | 0.059* | |
H14B | 1.0212 | 0.0035 | 0.8247 | 0.059* | |
H14C | 0.9708 | −0.0263 | 0.8863 | 0.059* | |
C6 | 0.92521 (12) | 0.1607 (3) | 0.6091 (2) | 0.0333 (5) | |
H6A | 0.9293 | 0.2637 | 0.6484 | 0.040* | |
H6B | 0.9678 | 0.1413 | 0.6020 | 0.040* | |
C15 | 0.66728 (11) | 0.0811 (3) | 0.4539 (2) | 0.0353 (5) | |
H15A | 0.6623 | 0.0042 | 0.3892 | 0.053* | |
H15B | 0.6695 | 0.1847 | 0.4225 | 0.053* | |
H15C | 0.6277 | 0.0748 | 0.4711 | 0.053* | |
C1 | 0.86483 (14) | 0.1610 (3) | 0.4775 (2) | 0.0381 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0323 (2) | 0.0170 (2) | 0.0308 (2) | −0.00179 (18) | 0.01245 (18) | 0.00069 (18) |
O8 | 0.0418 (8) | 0.0195 (7) | 0.0268 (7) | −0.0075 (6) | 0.0199 (6) | −0.0023 (6) |
O7 | 0.0324 (7) | 0.0207 (7) | 0.0221 (6) | −0.0001 (5) | 0.0138 (6) | −0.0002 (5) |
O6 | 0.0297 (7) | 0.0312 (8) | 0.0266 (7) | −0.0021 (6) | 0.0107 (6) | −0.0034 (6) |
C10 | 0.0257 (8) | 0.0244 (10) | 0.0192 (8) | 0.0008 (7) | 0.0109 (7) | 0.0017 (7) |
O9 | 0.0374 (8) | 0.0206 (7) | 0.0292 (7) | −0.0014 (6) | 0.0175 (6) | 0.0053 (6) |
C9 | 0.0254 (8) | 0.0175 (9) | 0.0236 (8) | 0.0001 (7) | 0.0117 (6) | −0.0022 (8) |
C11 | 0.0207 (8) | 0.0216 (10) | 0.0221 (8) | −0.0005 (7) | 0.0089 (7) | 0.0050 (7) |
C13 | 0.0236 (8) | 0.0192 (9) | 0.0200 (8) | 0.0007 (7) | 0.0096 (7) | 0.0022 (7) |
O10 | 0.0410 (8) | 0.0145 (7) | 0.0215 (6) | −0.0009 (5) | 0.0186 (6) | −0.0004 (5) |
C7 | 0.0290 (9) | 0.0197 (9) | 0.0212 (8) | −0.0032 (7) | 0.0141 (7) | −0.0004 (6) |
C12 | 0.0248 (8) | 0.0157 (9) | 0.0267 (8) | 0.0000 (7) | 0.0128 (7) | 0.0023 (7) |
C4 | 0.0298 (9) | 0.0194 (9) | 0.0208 (8) | 0.0005 (7) | 0.0124 (7) | 0.0007 (7) |
C3 | 0.0308 (9) | 0.0201 (9) | 0.0242 (9) | −0.0005 (7) | 0.0120 (7) | −0.0020 (7) |
C5 | 0.0299 (9) | 0.0321 (11) | 0.0246 (9) | −0.0055 (8) | 0.0141 (8) | −0.0070 (8) |
C17 | 0.0410 (11) | 0.0256 (10) | 0.0207 (8) | −0.0020 (8) | 0.0171 (8) | −0.0010 (7) |
C8 | 0.0279 (8) | 0.0212 (10) | 0.0231 (8) | −0.0005 (7) | 0.0131 (7) | 0.0004 (6) |
C16 | 0.0463 (12) | 0.0290 (12) | 0.0272 (10) | −0.0067 (9) | 0.0189 (9) | 0.0029 (8) |
O5 | 0.0671 (13) | 0.0784 (18) | 0.0367 (9) | −0.0186 (11) | 0.0304 (10) | 0.0053 (10) |
C2 | 0.0391 (10) | 0.0374 (13) | 0.0223 (8) | −0.0015 (10) | 0.0108 (8) | 0.0017 (9) |
C14 | 0.0300 (10) | 0.0539 (16) | 0.0311 (11) | 0.0008 (10) | 0.0117 (9) | −0.0075 (11) |
C6 | 0.0396 (11) | 0.0347 (13) | 0.0320 (10) | −0.0102 (10) | 0.0219 (9) | −0.0072 (9) |
C15 | 0.0291 (10) | 0.0380 (12) | 0.0322 (10) | 0.0007 (9) | 0.0085 (8) | −0.0050 (9) |
C1 | 0.0508 (12) | 0.0383 (14) | 0.0308 (10) | −0.0102 (11) | 0.0236 (10) | −0.0009 (10) |
Cl1—C12 | 1.721 (2) | C5—C6 | 1.519 (3) |
O8—C7 | 1.225 (2) | C5—C14 | 1.538 (3) |
O7—C13 | 1.357 (2) | C5—H5 | 1.0000 |
O7—C4 | 1.460 (2) | C17—H17A | 0.9800 |
O6—C3 | 1.336 (3) | C17—H17B | 0.9800 |
O6—C15 | 1.443 (3) | C17—H17C | 0.9800 |
C10—C9 | 1.389 (3) | C16—H16A | 0.9800 |
C10—C11 | 1.397 (3) | C16—H16B | 0.9800 |
C10—H10 | 0.9500 | C16—H16C | 0.9800 |
O9—C11 | 1.352 (2) | O5—C1 | 1.214 (3) |
O9—C16 | 1.443 (3) | C2—C1 | 1.462 (3) |
C9—O10 | 1.356 (2) | C2—H2 | 0.9500 |
C9—C8 | 1.404 (2) | C14—H14A | 0.9800 |
C11—C12 | 1.402 (3) | C14—H14B | 0.9800 |
C13—C12 | 1.389 (3) | C14—H14C | 0.9800 |
C13—C8 | 1.390 (3) | C6—C1 | 1.503 (3) |
O10—C17 | 1.438 (2) | C6—H6A | 0.9900 |
C7—C8 | 1.446 (3) | C6—H6B | 0.9900 |
C7—C4 | 1.558 (3) | C15—H15A | 0.9800 |
C4—C3 | 1.512 (3) | C15—H15B | 0.9800 |
C4—C5 | 1.531 (3) | C15—H15C | 0.9800 |
C3—C2 | 1.353 (3) | ||
C13—O7—C4 | 107.60 (15) | O10—C17—H17B | 109.5 |
C3—O6—C15 | 117.10 (18) | H17A—C17—H17B | 109.5 |
C9—C10—C11 | 119.99 (17) | O10—C17—H17C | 109.5 |
C9—C10—H10 | 120.0 | H17A—C17—H17C | 109.5 |
C11—C10—H10 | 120.0 | H17B—C17—H17C | 109.5 |
C11—O9—C16 | 118.55 (17) | C13—C8—C9 | 119.48 (18) |
O10—C9—C10 | 125.37 (17) | C13—C8—C7 | 107.16 (17) |
O10—C9—C8 | 115.43 (17) | C9—C8—C7 | 133.30 (19) |
C10—C9—C8 | 119.20 (19) | O9—C16—H16A | 109.5 |
O9—C11—C10 | 122.99 (18) | O9—C16—H16B | 109.5 |
O9—C11—C12 | 115.13 (18) | H16A—C16—H16B | 109.5 |
C10—C11—C12 | 121.88 (17) | O9—C16—H16C | 109.5 |
O7—C13—C12 | 122.41 (18) | H16A—C16—H16C | 109.5 |
O7—C13—C8 | 114.92 (16) | H16B—C16—H16C | 109.5 |
C12—C13—C8 | 122.68 (18) | C3—C2—C1 | 121.98 (19) |
C9—O10—C17 | 117.33 (15) | C3—C2—H2 | 119.0 |
O8—C7—C8 | 131.05 (18) | C1—C2—H2 | 119.0 |
O8—C7—C4 | 123.67 (17) | C5—C14—H14A | 109.5 |
C8—C7—C4 | 105.28 (16) | C5—C14—H14B | 109.5 |
C13—C12—C11 | 116.76 (18) | H14A—C14—H14B | 109.5 |
C13—C12—Cl1 | 120.73 (15) | C5—C14—H14C | 109.5 |
C11—C12—Cl1 | 122.51 (15) | H14A—C14—H14C | 109.5 |
O7—C4—C3 | 108.48 (16) | H14B—C14—H14C | 109.5 |
O7—C4—C5 | 107.19 (16) | C1—C6—C5 | 112.19 (18) |
C3—C4—C5 | 113.12 (16) | C1—C6—H6A | 109.2 |
O7—C4—C7 | 104.90 (14) | C5—C6—H6A | 109.2 |
C3—C4—C7 | 108.59 (16) | C1—C6—H6B | 109.2 |
C5—C4—C7 | 114.10 (16) | C5—C6—H6B | 109.2 |
O6—C3—C2 | 126.60 (19) | H6A—C6—H6B | 107.9 |
O6—C3—C4 | 111.27 (17) | O6—C15—H15A | 109.5 |
C2—C3—C4 | 122.03 (19) | O6—C15—H15B | 109.5 |
C6—C5—C4 | 111.24 (18) | H15A—C15—H15B | 109.5 |
C6—C5—C14 | 111.46 (19) | O6—C15—H15C | 109.5 |
C4—C5—C14 | 112.34 (17) | H15A—C15—H15C | 109.5 |
C6—C5—H5 | 107.2 | H15B—C15—H15C | 109.5 |
C4—C5—H5 | 107.2 | O5—C1—C2 | 121.3 (2) |
C14—C5—H5 | 107.2 | O5—C1—C6 | 121.1 (2) |
O10—C17—H17A | 109.5 | C2—C1—C6 | 117.56 (18) |
Experimental details
(GF-MeCN) | (GF-NM) | (GF-NE2-1) | (GF-NE1-1) | |
Crystal data | ||||
Chemical formula | C19H20ClNO6 | C18H20ClNO8 | C36H39Cl2NO14 | C19H22ClNO8 |
Mr | 393.81 | 413.80 | 780.58 | 427.83 |
Crystal system, space group | Monoclinic, P21 | Orthorhombic, P212121 | Orthorhombic, P212121 | Monoclinic, C2 |
Temperature (K) | 110 | 110 | 163 | 110 |
a, b, c (Å) | 11.783 (2), 8.5387 (17), 19.297 (4) | 8.5456 (17), 11.740 (2), 19.269 (4) | 8.6852 (17), 15.047 (3), 27.605 (6) | 21.931 (4), 8.6541 (17), 11.797 (2) |
α, β, γ (°) | 90, 96.03 (3), 90 | 90, 90, 90 | 90, 90, 90 | 90, 117.57 (3), 90 |
V (Å3) | 1930.8 (7) | 1933.2 (6) | 3607.6 (13) | 1984.7 (8) |
Z | 4 | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.23 | 0.24 | 0.25 | 0.24 |
Crystal size (mm) | 0.33 × 0.22 × 0.22 | 0.44 × 0.33 × 0.22 | 0.33 × 0.33 × 0.22 | 0.44 × 0.44 × 0.44 |
Data collection | ||||
Diffractometer | Rigaku Saturn 70 CCD area detector diffractometer | Rigaku Saturn 70 CCD area detector diffractometer | Rigaku Saturn 70 CCD area detector diffractometer | Rigaku Saturn 70 CCD area detector diffractometer |
Absorption correction | Multi-scan R. H. Blessing, Acta Cryst. 1995 A51, 33-38 | Multi-scan R. H. Blessing, Acta Cryst. 1995 A51, 33-38 | Multi-scan R. H. Blessing, Acta Cryst. 1995 A51, 33-38 | Multi-scan R. H. Blessing, Acta Cryst. 1995 A51, 33-38 |
Tmin, Tmax | 0.927, 0.951 | 0.900, 0.948 | 0.922, 0.947 | 0.910, 0.910 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 27812, 8585, 8103 | 15653, 4791, 4703 | 15583, 8492, 7628 | 7580, 4634, 4497 |
Rint | 0.030 | 0.026 | 0.029 | 0.016 |
(sin θ/λ)max (Å−1) | 0.667 | 0.667 | 0.666 | 0.667 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.152, 1.12 | 0.040, 0.110, 1.14 | 0.051, 0.117, 1.09 | 0.043, 0.119, 1.09 |
No. of reflections | 8585 | 4791 | 8492 | 4634 |
No. of parameters | 497 | 258 | 487 | 222 |
No. of restraints | 1 | 0 | 0 | 1 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.72, −0.38 | 0.28, −0.33 | 0.21, −0.35 | 0.43, −0.33 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | 0.05 (5) | −0.02 (6) | 0.01 (5) | 0.03 (6) |
Computer programs: CrystalClear (Rigaku Inc., 2007), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997).