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Four solvates of an antifungal drug, griseofulvin (GF), were discovered. All the solvates were characterized by differential scanning calorimetry, thermogravimetric analysis, and their crystal structures were determined by single-crystal X-ray diffraction. The solvents that form the solvates are acetonitrile, nitromethane and nitroethane (2:1 and 1:1). It was found that all the solvates lose the solvent molecules from the crystal lattice between 343 and 383 K, and that the melting point of the desolvated materials matched the melting point of the solvent-free GF (493 K). The conformation of the GF molecule in solvent-free form was found to be significantly different from the conformations found in the solvates. Solution stability studies revealed that the GF-acetonitrile solvate transforms to GF and that GF-nitroethane (1:1) solvate transforms to GF-nitroethane (2:1) solvate. On the other hand, GF-nitromethane and GF-nitroethane (2:1) solvates were found to be stable in solution. Our results highlight the importance of the co-crystallization technique in the pharmaceutical drug development; it not only expands the solid form diversity but also creates new avenues for unraveling novel solvates.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520613026711/zb5031sup1.cif
Contains datablocks GF-MeCN, GF-NM, GF-NE2-1, GF-NE1-1, publication_text

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520613026711/zb5031GF-MeCNsup2.hkl
Contains datablock GF-MeCN

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520613026711/zb5031GF-NMsup3.hkl
Contains datablock GF-NM

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520613026711/zb5031GF-NE2-1sup4.hkl
Contains datablock GF-NE2-1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520613026711/zb5031GF-NE1-1sup5.hkl
Contains datablock GF-NE1-1

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520613026711/zb5031sup6.pdf
This material contains a comparison of 1H NMR spectra of the nitroethane solvates, an ORTEP plot and a packing diagram of GF-nitroethane (1:1) solvate, and PXRD patterns and SEM images of the desolvated crystals

txt

Text file https://doi.org/10.1107/S2052520613026711/zb5031sup7.txt
CIF file for the crystal structure of GF-nitroethane (1:1) with guest molecule

txt

Text file https://doi.org/10.1107/S2052520613026711/zb5031sup8.txt
Structure factors file for the crystal structure of GF-nitroethane (1:1) with guest molecule

CCDC references: 924889; 924890; 924891; 924892

Computing details top

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).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
(GF-MeCN) top
Crystal data top
C19H20ClNO6F(000) = 824
Mr = 393.81Dx = 1.355 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4495 reflections
a = 11.783 (2) Åθ = 2.1–31.2°
b = 8.5387 (17) ŵ = 0.23 mm1
c = 19.297 (4) ÅT = 110 K
β = 96.03 (3)°Block, colorless
V = 1930.8 (7) Å30.33 × 0.22 × 0.22 mm
Z = 4
Data collection top
Rigaku Saturn 70 CCD area detector
diffractometer
8585 independent reflections
Radiation source: fine-focus sealed tube8103 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ω scansθmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan
R. H. Blessing, Acta Cryst. 1995 A51, 33-38
h = 1515
Tmin = 0.927, Tmax = 0.951k = 711
27812 measured reflectionsl = 2525
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H-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 reflectionsΔρmax = 0.72 e Å3
497 parametersΔρmin = 0.38 e Å3
1 restraintAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.05 (5)
Crystal data top
C19H20ClNO6V = 1930.8 (7) Å3
Mr = 393.81Z = 4
Monoclinic, P21Mo Kα radiation
a = 11.783 (2) ŵ = 0.23 mm1
b = 8.5387 (17) ÅT = 110 K
c = 19.297 (4) Å0.33 × 0.22 × 0.22 mm
β = 96.03 (3)°
Data collection top
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 = 0.951Rint = 0.030
27812 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.152Δρmax = 0.72 e Å3
S = 1.12Δρmin = 0.38 e Å3
8585 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
497 parametersAbsolute structure parameter: 0.05 (5)
1 restraint
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.17274 (5)0.38730 (7)0.57342 (3)0.0274 (3)
O60.07655 (16)0.2852 (2)0.60335 (10)0.0283 (5)
O50.05399 (16)0.2508 (2)0.57137 (10)0.0280 (5)
O20.41387 (17)0.0290 (2)0.48152 (9)0.0296 (5)
O30.33767 (15)0.1177 (2)0.58766 (9)0.0252 (4)
O40.33621 (17)0.2953 (3)0.61322 (12)0.0347 (5)
C120.1396 (2)0.1917 (3)0.57868 (13)0.0231 (5)
C100.0019 (2)0.0204 (3)0.58558 (13)0.0234 (5)
H100.07520.05370.58470.028*
C130.2248 (2)0.0810 (3)0.58558 (13)0.0226 (5)
C90.0902 (2)0.1297 (3)0.59381 (12)0.0227 (5)
C30.4750 (2)0.0562 (3)0.54332 (13)0.0260 (6)
C50.4759 (2)0.0011 (4)0.67142 (14)0.0298 (6)
H50.51730.10050.66810.036*
C40.4027 (2)0.0244 (3)0.60253 (13)0.0251 (6)
C20.5817 (2)0.1114 (4)0.55394 (15)0.0343 (7)
H20.62320.12860.51500.041*
C110.0271 (2)0.1379 (3)0.57867 (13)0.0237 (6)
C170.0362 (2)0.3414 (4)0.61033 (15)0.0295 (6)
H17A0.08680.31410.56850.044*
H17B0.03430.45540.61600.044*
H17C0.06460.29300.65120.044*
C80.2038 (2)0.0785 (3)0.59394 (12)0.0245 (6)
C60.5659 (2)0.1282 (4)0.68391 (15)0.0354 (7)
H6A0.52820.22910.69210.042*
H6B0.61740.10250.72630.042*
C160.1709 (2)0.2067 (4)0.57173 (16)0.0318 (6)
H16A0.18200.15830.61660.048*
H16B0.21930.29990.56480.048*
H16C0.19160.13180.53410.048*
C70.3120 (2)0.1568 (3)0.60419 (14)0.0270 (6)
C140.4039 (3)0.0134 (5)0.73274 (15)0.0412 (8)
H14A0.36820.08770.74080.062*
H14B0.45300.04440.77470.062*
H14C0.34460.09270.72200.062*
O10.7343 (2)0.1935 (5)0.63221 (15)0.0749 (11)
C10.6354 (3)0.1454 (4)0.62303 (17)0.0411 (8)
C150.4690 (3)0.0644 (4)0.41999 (15)0.0390 (7)
H15A0.49630.17290.42240.059*
H15B0.41440.05100.37850.059*
H15C0.53380.00650.41740.059*
Cl20.33007 (5)0.34949 (7)0.92510 (3)0.0266 (2)
O2A0.09083 (16)0.0651 (2)1.02207 (9)0.0268 (4)
O5A0.55669 (16)0.2131 (2)0.92697 (10)0.0278 (5)
O4A0.16645 (16)0.3338 (2)0.89310 (11)0.0301 (5)
O6A0.42572 (15)0.3235 (2)0.89871 (10)0.0275 (5)
O3A0.16576 (15)0.0801 (2)0.91476 (10)0.0233 (4)
C10A0.5010 (2)0.0596 (3)0.91456 (12)0.0226 (5)
H10A0.57790.09320.91480.027*
C12A0.3634 (2)0.1535 (3)0.92137 (12)0.0217 (5)
C4A0.1003 (2)0.0626 (3)0.90149 (13)0.0226 (5)
C13A0.2781 (2)0.0428 (3)0.91600 (12)0.0230 (5)
C17A0.5383 (2)0.3794 (4)0.88976 (16)0.0304 (6)
H17D0.59080.35060.93050.046*
H17E0.53660.49360.88470.046*
H17F0.56420.33210.84790.046*
C5A0.0272 (2)0.0418 (3)0.83159 (13)0.0266 (6)
H5A0.01280.06110.83360.032*
C9A0.4130 (2)0.1685 (3)0.90752 (13)0.0232 (5)
C16A0.6738 (2)0.1686 (4)0.92828 (16)0.0320 (6)
H16D0.68590.11660.88440.048*
H16E0.72210.26210.93410.048*
H16F0.69370.09660.96720.048*
C11A0.4762 (2)0.1000 (3)0.92128 (12)0.0222 (5)
C8A0.2991 (2)0.1169 (3)0.90873 (12)0.0223 (5)
C2A0.0793 (2)0.1430 (4)0.95125 (14)0.0304 (6)
H2A0.12020.15810.99060.037*
O1A0.2347 (2)0.2197 (4)0.87353 (14)0.0576 (8)
C3A0.0287 (2)0.0903 (3)0.96098 (13)0.0239 (5)
C6A0.0647 (2)0.1674 (4)0.82138 (15)0.0323 (6)
H6AA0.02820.27010.81500.039*
H6AB0.11570.14410.77850.039*
C7A0.1908 (2)0.1954 (3)0.90038 (13)0.0250 (5)
C14A0.0994 (3)0.0334 (4)0.77016 (14)0.0345 (7)
H14D0.05040.00660.72760.052*
H14E0.15840.04700.77940.052*
H14F0.13560.13510.76420.052*
C15A0.0374 (3)0.0976 (4)1.08422 (14)0.0357 (7)
H15D0.00850.20531.08250.054*
H15E0.09350.08501.12510.054*
H15F0.02600.02471.08740.054*
C1A0.1351 (2)0.1777 (4)0.88225 (16)0.0361 (7)
C190.1418 (4)0.5705 (5)0.75574 (17)0.0517 (9)
C180.2531 (3)0.5048 (6)0.75057 (15)0.0522 (10)
H18A0.24900.43040.71170.078*
H18B0.27930.45040.79400.078*
H18C0.30670.58890.74250.078*
N10.0511 (4)0.6227 (6)0.75849 (19)0.0726 (11)
C200.2377 (5)0.0165 (9)0.2543 (2)0.113 (3)
H20A0.27430.07520.21910.169*
H20B0.15460.02450.24450.169*
H20C0.26140.06010.30060.169*
C210.2732 (8)0.1546 (12)0.2525 (3)0.158 (5)
N20.3132 (13)0.2683 (12)0.2498 (3)0.281 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0273 (4)0.0222 (7)0.0331 (3)0.0018 (2)0.0047 (3)0.0012 (2)
O60.0225 (9)0.0206 (12)0.0427 (10)0.0006 (7)0.0082 (8)0.0030 (8)
O50.0214 (9)0.0277 (12)0.0348 (10)0.0062 (8)0.0017 (7)0.0020 (8)
O20.0293 (10)0.0330 (13)0.0275 (9)0.0001 (8)0.0078 (7)0.0014 (8)
O30.0202 (9)0.0244 (12)0.0316 (9)0.0017 (7)0.0060 (7)0.0024 (8)
O40.0266 (10)0.0252 (12)0.0535 (13)0.0061 (8)0.0104 (9)0.0082 (9)
C120.0209 (12)0.0222 (15)0.0260 (11)0.0010 (10)0.0005 (9)0.0000 (10)
C100.0186 (11)0.0261 (15)0.0254 (11)0.0029 (10)0.0024 (9)0.0002 (10)
C130.0145 (11)0.0276 (16)0.0263 (11)0.0026 (9)0.0046 (8)0.0000 (10)
C90.0215 (12)0.0215 (15)0.0260 (11)0.0014 (10)0.0060 (9)0.0003 (10)
C30.0261 (13)0.0256 (15)0.0274 (11)0.0004 (10)0.0072 (9)0.0005 (10)
C50.0248 (13)0.0363 (18)0.0286 (12)0.0042 (11)0.0050 (10)0.0043 (11)
C40.0221 (12)0.0247 (15)0.0289 (12)0.0030 (10)0.0048 (9)0.0042 (10)
C20.0239 (13)0.041 (2)0.0410 (14)0.0036 (12)0.0154 (11)0.0001 (13)
C110.0220 (12)0.0265 (15)0.0227 (11)0.0070 (10)0.0027 (9)0.0019 (10)
C170.0225 (13)0.0281 (16)0.0389 (14)0.0000 (11)0.0081 (10)0.0039 (11)
C80.0205 (12)0.0278 (16)0.0259 (11)0.0029 (10)0.0062 (9)0.0027 (10)
C60.0261 (14)0.044 (2)0.0359 (14)0.0042 (13)0.0013 (11)0.0112 (13)
C160.0195 (12)0.0300 (16)0.0457 (15)0.0049 (11)0.0018 (11)0.0014 (12)
C70.0224 (12)0.0266 (16)0.0333 (13)0.0047 (11)0.0093 (10)0.0034 (11)
C140.0356 (16)0.060 (2)0.0284 (14)0.0067 (15)0.0049 (12)0.0008 (14)
O10.0330 (14)0.128 (3)0.0646 (17)0.0385 (17)0.0107 (12)0.0190 (19)
C10.0256 (14)0.049 (2)0.0494 (17)0.0094 (14)0.0069 (12)0.0076 (15)
C150.0401 (17)0.048 (2)0.0312 (13)0.0010 (15)0.0145 (12)0.0040 (13)
Cl20.0254 (3)0.0189 (6)0.0358 (3)0.0017 (2)0.0045 (3)0.0015 (2)
O2A0.0265 (9)0.0291 (12)0.0255 (8)0.0010 (8)0.0054 (7)0.0010 (7)
O5A0.0200 (9)0.0246 (12)0.0386 (10)0.0064 (8)0.0023 (7)0.0001 (8)
O4A0.0242 (10)0.0225 (12)0.0447 (11)0.0054 (8)0.0083 (8)0.0064 (8)
O6A0.0177 (9)0.0206 (12)0.0452 (11)0.0004 (7)0.0076 (7)0.0029 (8)
O3A0.0176 (8)0.0198 (11)0.0330 (9)0.0023 (7)0.0049 (7)0.0013 (7)
C10A0.0162 (11)0.0254 (15)0.0264 (11)0.0024 (10)0.0027 (8)0.0005 (10)
C12A0.0234 (12)0.0193 (14)0.0221 (11)0.0014 (10)0.0007 (9)0.0003 (9)
C4A0.0159 (11)0.0209 (14)0.0315 (12)0.0014 (9)0.0051 (9)0.0020 (10)
C13A0.0195 (11)0.0275 (15)0.0222 (11)0.0031 (10)0.0034 (9)0.0008 (10)
C17A0.0191 (12)0.0251 (16)0.0483 (16)0.0000 (10)0.0095 (11)0.0026 (12)
C5A0.0220 (12)0.0284 (16)0.0299 (12)0.0014 (10)0.0049 (9)0.0017 (10)
C9A0.0210 (12)0.0208 (15)0.0285 (11)0.0007 (10)0.0054 (9)0.0030 (10)
C16A0.0181 (12)0.0312 (17)0.0467 (16)0.0044 (11)0.0044 (11)0.0005 (12)
C11A0.0174 (11)0.0250 (15)0.0244 (11)0.0054 (10)0.0035 (8)0.0000 (10)
C8A0.0193 (11)0.0224 (15)0.0256 (11)0.0014 (10)0.0049 (9)0.0024 (9)
C2A0.0236 (13)0.0344 (17)0.0350 (13)0.0041 (11)0.0109 (10)0.0006 (12)
O1A0.0239 (11)0.087 (2)0.0619 (15)0.0208 (12)0.0058 (10)0.0132 (15)
C3A0.0219 (12)0.0216 (14)0.0286 (11)0.0018 (10)0.0055 (9)0.0023 (10)
C6A0.0221 (13)0.0383 (18)0.0364 (13)0.0040 (12)0.0031 (10)0.0095 (12)
C7A0.0211 (12)0.0279 (15)0.0268 (11)0.0013 (10)0.0059 (9)0.0026 (10)
C14A0.0327 (15)0.0420 (19)0.0289 (13)0.0030 (13)0.0041 (11)0.0013 (12)
C15A0.0399 (16)0.0396 (19)0.0288 (13)0.0069 (14)0.0096 (11)0.0020 (12)
C1A0.0225 (13)0.044 (2)0.0426 (15)0.0090 (12)0.0056 (11)0.0062 (14)
C190.073 (3)0.045 (2)0.0376 (16)0.015 (2)0.0118 (16)0.0028 (15)
C180.068 (3)0.052 (2)0.0369 (18)0.0002 (18)0.0091 (17)0.0033 (15)
N10.065 (2)0.092 (3)0.062 (2)0.003 (2)0.0127 (18)0.010 (2)
C200.157 (6)0.118 (6)0.056 (3)0.094 (5)0.024 (3)0.021 (3)
C210.216 (9)0.198 (10)0.055 (3)0.176 (8)0.009 (4)0.003 (4)
N20.560 (18)0.184 (9)0.079 (4)0.233 (12)0.060 (7)0.033 (4)
Geometric parameters (Å, º) top
Cl1—C121.721 (3)O4A—C7A1.220 (4)
O6—C91.352 (3)O6A—C9A1.345 (3)
O6—C171.432 (3)O6A—C17A1.437 (3)
O5—C111.354 (3)O3A—C13A1.360 (3)
O5—C161.429 (3)O3A—C4A1.450 (3)
O2—C31.347 (3)C10A—C9A1.389 (3)
O2—C151.444 (3)C10A—C11A1.403 (4)
O3—C131.363 (3)C10A—H10A0.9500
O3—C41.448 (3)C12A—C13A1.376 (4)
O4—C71.225 (4)C12A—C11A1.405 (3)
C12—C131.376 (4)C4A—C3A1.513 (3)
C12—C111.402 (4)C4A—C5A1.533 (4)
C10—C111.394 (4)C4A—C7A1.558 (4)
C10—C91.394 (4)C13A—C8A1.395 (4)
C10—H100.9500C17A—H17D0.9800
C13—C81.397 (4)C17A—H17E0.9800
C9—C81.408 (3)C17A—H17F0.9800
C3—C21.338 (4)C5A—C6A1.523 (4)
C3—C41.520 (3)C5A—C14A1.532 (4)
C5—C61.519 (4)C5A—H5A1.0000
C5—C41.520 (4)C9A—C8A1.415 (3)
C5—C141.532 (4)C16A—H16D0.9800
C5—H51.0000C16A—H16E0.9800
C4—C71.559 (4)C16A—H16F0.9800
C2—C11.444 (4)C8A—C7A1.435 (4)
C2—H20.9500C2A—C3A1.345 (4)
C17—H17A0.9800C2A—C1A1.452 (4)
C17—H17B0.9800C2A—H2A0.9500
C17—H17C0.9800O1A—C1A1.221 (4)
C8—C71.434 (4)C6A—C1A1.510 (4)
C6—C11.508 (4)C6A—H6AA0.9900
C6—H6A0.9900C6A—H6AB0.9900
C6—H6B0.9900C14A—H14D0.9800
C16—H16A0.9800C14A—H14E0.9800
C16—H16B0.9800C14A—H14F0.9800
C16—H16C0.9800C15A—H15D0.9800
C14—H14A0.9800C15A—H15E0.9800
C14—H14B0.9800C15A—H15F0.9800
C14—H14C0.9800C19—N11.164 (5)
O1—C11.231 (4)C19—C181.439 (5)
C15—H15A0.9800C18—H18A0.9800
C15—H15B0.9800C18—H18B0.9800
C15—H15C0.9800C18—H18C0.9800
Cl2—C12A1.722 (3)C20—C211.521 (11)
O2A—C3A1.338 (3)C20—H20A0.9800
O2A—C15A1.439 (3)C20—H20B0.9800
O5A—C11A1.350 (3)C20—H20C0.9800
O5A—C16A1.429 (3)C21—N21.082 (9)
C9—O6—C17117.8 (2)C13A—C12A—C11A117.4 (2)
C11—O5—C16118.9 (2)C13A—C12A—Cl2120.2 (2)
C3—O2—C15116.5 (2)C11A—C12A—Cl2122.4 (2)
C13—O3—C4107.9 (2)O3A—C4A—C3A109.0 (2)
C13—C12—C11117.1 (3)O3A—C4A—C5A107.3 (2)
C13—C12—Cl1120.3 (2)C3A—C4A—C5A112.3 (2)
C11—C12—Cl1122.5 (2)O3A—C4A—C7A105.19 (19)
C11—C10—C9119.7 (2)C3A—C4A—C7A109.5 (2)
C11—C10—H10120.1C5A—C4A—C7A113.2 (2)
C9—C10—H10120.1O3A—C13A—C12A122.9 (3)
O3—C13—C12123.0 (3)O3A—C13A—C8A114.2 (2)
O3—C13—C8113.9 (2)C12A—C13A—C8A122.9 (2)
C12—C13—C8123.0 (2)O6A—C17A—H17D109.5
O6—C9—C10125.1 (2)O6A—C17A—H17E109.5
O6—C9—C8115.5 (2)H17D—C17A—H17E109.5
C10—C9—C8119.4 (3)O6A—C17A—H17F109.5
C2—C3—O2127.1 (2)H17D—C17A—H17F109.5
C2—C3—C4122.7 (2)H17E—C17A—H17F109.5
O2—C3—C4110.2 (2)C6A—C5A—C14A112.2 (2)
C6—C5—C4111.6 (2)C6A—C5A—C4A111.0 (2)
C6—C5—C14111.7 (2)C14A—C5A—C4A112.3 (2)
C4—C5—C14112.1 (2)C6A—C5A—H5A107.0
C6—C5—H5107.0C14A—C5A—H5A107.0
C4—C5—H5107.0C4A—C5A—H5A107.0
C14—C5—H5107.0O6A—C9A—C10A125.4 (2)
O3—C4—C3109.1 (2)O6A—C9A—C8A115.3 (2)
O3—C4—C5107.7 (2)C10A—C9A—C8A119.4 (3)
C3—C4—C5111.7 (2)O5A—C16A—H16D109.5
O3—C4—C7105.2 (2)O5A—C16A—H16E109.5
C3—C4—C7109.0 (2)H16D—C16A—H16E109.5
C5—C4—C7113.9 (2)O5A—C16A—H16F109.5
C3—C2—C1121.7 (2)H16D—C16A—H16F109.5
C3—C2—H2119.1H16E—C16A—H16F109.5
C1—C2—H2119.1O5A—C11A—C10A123.4 (2)
O5—C11—C10123.0 (2)O5A—C11A—C12A115.1 (2)
O5—C11—C12115.1 (2)C10A—C11A—C12A121.5 (2)
C10—C11—C12121.9 (2)C13A—C8A—C9A118.9 (2)
O6—C17—H17A109.5C13A—C8A—C7A107.7 (2)
O6—C17—H17B109.5C9A—C8A—C7A133.3 (3)
H17A—C17—H17B109.5C3A—C2A—C1A121.8 (2)
O6—C17—H17C109.5C3A—C2A—H2A119.1
H17A—C17—H17C109.5C1A—C2A—H2A119.1
H17B—C17—H17C109.5O2A—C3A—C2A126.8 (2)
C13—C8—C9118.8 (2)O2A—C3A—C4A110.3 (2)
C13—C8—C7107.7 (2)C2A—C3A—C4A122.8 (2)
C9—C8—C7133.4 (3)C1A—C6A—C5A112.4 (2)
C1—C6—C5111.9 (2)C1A—C6A—H6AA109.1
C1—C6—H6A109.2C5A—C6A—H6AA109.1
C5—C6—H6A109.2C1A—C6A—H6AB109.1
C1—C6—H6B109.2C5A—C6A—H6AB109.1
C5—C6—H6B109.2H6AA—C6A—H6AB107.8
H6A—C6—H6B107.9O4A—C7A—C8A131.4 (3)
O5—C16—H16A109.5O4A—C7A—C4A123.6 (2)
O5—C16—H16B109.5C8A—C7A—C4A105.1 (2)
H16A—C16—H16B109.5C5A—C14A—H14D109.5
O5—C16—H16C109.5C5A—C14A—H14E109.5
H16A—C16—H16C109.5H14D—C14A—H14E109.5
H16B—C16—H16C109.5C5A—C14A—H14F109.5
O4—C7—C8131.3 (3)H14D—C14A—H14F109.5
O4—C7—C4123.6 (2)H14E—C14A—H14F109.5
C8—C7—C4105.1 (2)O2A—C15A—H15D109.5
C5—C14—H14A109.5O2A—C15A—H15E109.5
C5—C14—H14B109.5H15D—C15A—H15E109.5
H14A—C14—H14B109.5O2A—C15A—H15F109.5
C5—C14—H14C109.5H15D—C15A—H15F109.5
H14A—C14—H14C109.5H15E—C15A—H15F109.5
H14B—C14—H14C109.5O1A—C1A—C2A121.5 (3)
O1—C1—C2121.1 (3)O1A—C1A—C6A120.5 (3)
O1—C1—C6120.2 (3)C2A—C1A—C6A117.9 (2)
C2—C1—C6118.6 (2)N1—C19—C18178.6 (4)
O2—C15—H15A109.5C19—C18—H18A109.5
O2—C15—H15B109.5C19—C18—H18B109.5
H15A—C15—H15B109.5H18A—C18—H18B109.5
O2—C15—H15C109.5C19—C18—H18C109.5
H15A—C15—H15C109.5H18A—C18—H18C109.5
H15B—C15—H15C109.5H18B—C18—H18C109.5
C3A—O2A—C15A117.2 (2)C21—C20—H20A109.5
C11A—O5A—C16A118.7 (2)C21—C20—H20B109.5
C9A—O6A—C17A117.3 (2)H20A—C20—H20B109.5
C13A—O3A—C4A107.7 (2)C21—C20—H20C109.5
C9A—C10A—C11A119.9 (2)H20A—C20—H20C109.5
C9A—C10A—H10A120.1H20B—C20—H20C109.5
C11A—C10A—H10A120.1N2—C21—C20169.8 (16)
(GF-NM) top
Crystal data top
C18H20ClNO8F(000) = 864
Mr = 413.80Dx = 1.422 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5198 reflections
a = 8.5456 (17) Åθ = 2.0–31.1°
b = 11.740 (2) ŵ = 0.24 mm1
c = 19.269 (4) ÅT = 110 K
V = 1933.2 (6) Å3Block, colorless
Z = 40.44 × 0.33 × 0.22 mm
Data collection top
Rigaku Saturn 70 CCD area detector
diffractometer
4791 independent reflections
Radiation source: fine-focus sealed tube4703 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
ω scansθmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan
R. H. Blessing, Acta Cryst. 1995 A51, 33-38
h = 119
Tmin = 0.900, Tmax = 0.948k = 1515
15653 measured reflectionsl = 2525
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-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 reflectionsΔρmax = 0.28 e Å3
258 parametersΔρmin = 0.33 e Å3
0 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (6)
Crystal data top
C18H20ClNO8V = 1933.2 (6) Å3
Mr = 413.80Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.5456 (17) ŵ = 0.24 mm1
b = 11.740 (2) ÅT = 110 K
c = 19.269 (4) Å0.44 × 0.33 × 0.22 mm
Data collection top
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 = 0.948Rint = 0.026
15653 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.110Δρmax = 0.28 e Å3
S = 1.14Δρmin = 0.33 e Å3
4791 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
258 parametersAbsolute structure parameter: 0.02 (6)
0 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.10461 (5)0.09159 (4)0.07669 (2)0.02513 (11)
O50.24075 (15)0.31871 (11)0.07482 (8)0.0256 (3)
O40.78786 (16)0.06498 (11)0.11357 (8)0.0256 (3)
O30.37426 (15)0.07102 (10)0.09214 (7)0.0207 (3)
O60.77866 (15)0.19309 (11)0.09915 (7)0.0237 (3)
O20.51498 (17)0.16627 (11)0.01456 (7)0.0256 (3)
C120.3000 (2)0.12555 (15)0.08278 (9)0.0203 (3)
C110.3537 (2)0.23895 (14)0.08133 (9)0.0202 (3)
C100.5141 (2)0.26543 (14)0.08674 (9)0.0202 (3)
H100.54770.34250.08560.024*
C80.57096 (19)0.06441 (14)0.09584 (9)0.0189 (3)
C70.6497 (2)0.04254 (15)0.10602 (9)0.0197 (3)
C130.4106 (2)0.04154 (14)0.08966 (9)0.0194 (3)
C90.6231 (2)0.17802 (14)0.09384 (9)0.0192 (3)
C160.2862 (2)0.43617 (14)0.06938 (11)0.0278 (4)
H16A0.34140.45910.11170.042*
H16B0.19280.48360.06340.042*
H16C0.35550.44590.02930.042*
C170.8349 (2)0.30797 (15)0.10406 (11)0.0242 (4)
H17A0.80430.35030.06240.036*
H17B0.94920.30750.10810.036*
H17C0.78950.34460.14510.036*
C40.5174 (2)0.13393 (14)0.10556 (9)0.0202 (3)
C30.5468 (2)0.21592 (15)0.04676 (10)0.0225 (4)
C50.4961 (2)0.19527 (16)0.17478 (10)0.0246 (4)
H50.39550.23860.17190.029*
O10.7042 (3)0.45623 (15)0.13399 (10)0.0563 (6)
C20.6076 (3)0.31998 (16)0.05644 (10)0.0295 (4)
H20.62380.36810.01740.035*
C60.6264 (3)0.28207 (16)0.18613 (11)0.0297 (4)
H6A0.72560.24100.19510.036*
H6B0.60180.32790.22790.036*
C150.5478 (3)0.23158 (19)0.07599 (11)0.0344 (5)
H15A0.65970.24940.07780.052*
H15B0.51840.18740.11710.052*
H15C0.48740.30260.07490.052*
C140.4816 (3)0.11285 (19)0.23569 (10)0.0328 (5)
H14A0.45740.15560.27810.049*
H14B0.39760.05820.22640.049*
H14C0.58060.07190.24180.049*
C10.6492 (3)0.36114 (17)0.12535 (12)0.0334 (5)
N10.0925 (3)0.60691 (17)0.24641 (10)0.0380 (4)
O70.0178 (3)0.69429 (16)0.25471 (10)0.0544 (5)
C180.0079 (3)0.4970 (2)0.24978 (14)0.0414 (5)
H18A0.00700.47520.29840.062*
H18B0.06900.43820.22590.062*
H18C0.09430.50490.22720.062*
O80.2333 (3)0.60421 (19)0.23539 (12)0.0596 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.01660 (18)0.0255 (2)0.0333 (2)0.00091 (16)0.00179 (17)0.00053 (17)
O50.0198 (6)0.0194 (6)0.0376 (7)0.0048 (5)0.0016 (6)0.0023 (6)
O40.0173 (6)0.0222 (6)0.0373 (7)0.0031 (5)0.0036 (5)0.0010 (5)
O30.0165 (6)0.0161 (5)0.0294 (6)0.0001 (4)0.0005 (5)0.0000 (4)
O60.0166 (6)0.0170 (6)0.0374 (7)0.0003 (5)0.0012 (5)0.0023 (5)
O20.0289 (7)0.0255 (6)0.0223 (6)0.0002 (6)0.0012 (5)0.0019 (5)
C120.0167 (8)0.0215 (8)0.0225 (8)0.0010 (6)0.0017 (6)0.0014 (6)
C110.0185 (8)0.0194 (7)0.0228 (8)0.0049 (6)0.0011 (6)0.0001 (6)
C100.0204 (8)0.0171 (7)0.0229 (8)0.0004 (6)0.0013 (7)0.0010 (6)
C80.0165 (8)0.0181 (7)0.0222 (8)0.0009 (6)0.0021 (6)0.0016 (6)
C70.0202 (8)0.0175 (7)0.0213 (8)0.0016 (6)0.0007 (6)0.0009 (6)
C130.0205 (8)0.0160 (7)0.0218 (7)0.0003 (6)0.0010 (6)0.0008 (6)
C90.0167 (8)0.0177 (7)0.0233 (8)0.0004 (6)0.0005 (6)0.0017 (6)
C160.0263 (9)0.0189 (8)0.0382 (10)0.0061 (7)0.0016 (8)0.0024 (7)
C170.0198 (8)0.0177 (7)0.0350 (9)0.0014 (6)0.0005 (7)0.0023 (7)
C40.0198 (8)0.0166 (7)0.0242 (8)0.0012 (6)0.0004 (7)0.0014 (6)
C30.0211 (8)0.0202 (8)0.0261 (8)0.0019 (7)0.0004 (7)0.0007 (7)
C50.0251 (9)0.0220 (8)0.0267 (8)0.0005 (7)0.0016 (7)0.0019 (7)
O10.0879 (16)0.0271 (8)0.0538 (11)0.0247 (10)0.0044 (11)0.0036 (7)
C20.0355 (10)0.0197 (8)0.0333 (9)0.0011 (8)0.0026 (8)0.0048 (7)
C60.0357 (11)0.0230 (8)0.0303 (9)0.0025 (8)0.0052 (8)0.0051 (7)
C150.0424 (12)0.0367 (10)0.0241 (9)0.0062 (9)0.0032 (9)0.0074 (9)
C140.0398 (12)0.0356 (11)0.0232 (9)0.0055 (9)0.0040 (8)0.0006 (8)
C10.0400 (12)0.0201 (8)0.0400 (11)0.0070 (8)0.0009 (9)0.0017 (8)
N10.0457 (12)0.0394 (10)0.0290 (8)0.0033 (9)0.0066 (8)0.0047 (7)
O70.0738 (14)0.0436 (10)0.0457 (10)0.0145 (10)0.0172 (10)0.0040 (8)
C180.0397 (13)0.0449 (14)0.0395 (11)0.0027 (10)0.0083 (10)0.0010 (10)
O80.0510 (12)0.0610 (12)0.0669 (13)0.0056 (11)0.0095 (10)0.0192 (11)
Geometric parameters (Å, º) top
Cl1—C121.7208 (18)C4—C31.508 (2)
O5—C111.351 (2)C4—C51.527 (3)
O5—C161.437 (2)C3—C21.340 (3)
O4—C71.218 (2)C5—C61.525 (3)
O3—C131.3584 (19)C5—C141.526 (3)
O3—C41.452 (2)C5—H51.0000
O6—C91.345 (2)O1—C11.223 (3)
O6—C171.435 (2)C2—C11.457 (3)
O2—C31.345 (2)C2—H20.9500
O2—C151.438 (2)C6—C11.507 (3)
C12—C131.372 (2)C6—H6A0.9900
C12—C111.408 (2)C6—H6B0.9900
C11—C101.409 (2)C15—H15A0.9800
C10—C91.393 (2)C15—H15B0.9800
C10—H100.9500C15—H15C0.9800
C8—C131.401 (2)C14—H14A0.9800
C8—C91.407 (2)C14—H14B0.9800
C8—C71.438 (2)C14—H14C0.9800
C7—C41.559 (3)N1—O71.219 (3)
C16—H16A0.9800N1—O81.222 (3)
C16—H16B0.9800N1—C181.480 (3)
C16—H16C0.9800C18—H18A0.9800
C17—H17A0.9800C18—H18B0.9800
C17—H17B0.9800C18—H18C0.9800
C17—H17C0.9800
C11—O5—C16118.61 (14)C2—C3—O2126.55 (17)
C13—O3—C4107.95 (13)C2—C3—C4122.80 (17)
C9—O6—C17117.36 (14)O2—C3—C4110.46 (15)
C3—O2—C15116.91 (15)C6—C5—C14111.86 (16)
C13—C12—C11117.18 (16)C6—C5—C4110.68 (16)
C13—C12—Cl1120.55 (13)C14—C5—C4112.49 (15)
C11—C12—Cl1122.27 (13)C6—C5—H5107.2
O5—C11—C12115.10 (15)C14—C5—H5107.2
O5—C11—C10123.30 (15)C4—C5—H5107.2
C12—C11—C10121.60 (15)C3—C2—C1121.58 (18)
C9—C10—C11119.69 (16)C3—C2—H2119.2
C9—C10—H10120.2C1—C2—H2119.2
C11—C10—H10120.2C1—C6—C5113.23 (17)
C13—C8—C9119.28 (15)C1—C6—H6A108.9
C13—C8—C7107.59 (15)C5—C6—H6A108.9
C9—C8—C7133.09 (16)C1—C6—H6B108.9
O4—C7—C8131.21 (17)C5—C6—H6B108.9
O4—C7—C4123.70 (16)H6A—C6—H6B107.7
C8—C7—C4105.10 (14)O2—C15—H15A109.5
O3—C13—C12123.02 (16)O2—C15—H15B109.5
O3—C13—C8114.02 (15)H15A—C15—H15B109.5
C12—C13—C8122.95 (16)O2—C15—H15C109.5
O6—C9—C10124.87 (16)H15A—C15—H15C109.5
O6—C9—C8115.84 (15)H15B—C15—H15C109.5
C10—C9—C8119.29 (16)C5—C14—H14A109.5
O5—C16—H16A109.5C5—C14—H14B109.5
O5—C16—H16B109.5H14A—C14—H14B109.5
H16A—C16—H16B109.5C5—C14—H14C109.5
O5—C16—H16C109.5H14A—C14—H14C109.5
H16A—C16—H16C109.5H14B—C14—H14C109.5
H16B—C16—H16C109.5O1—C1—C2121.4 (2)
O6—C17—H17A109.5O1—C1—C6120.4 (2)
O6—C17—H17B109.5C2—C1—C6118.19 (17)
H17A—C17—H17B109.5O7—N1—O8124.1 (3)
O6—C17—H17C109.5O7—N1—C18118.1 (2)
H17A—C17—H17C109.5O8—N1—C18117.8 (2)
H17B—C17—H17C109.5N1—C18—H18A109.5
O3—C4—C3109.35 (14)N1—C18—H18B109.5
O3—C4—C5107.14 (15)H18A—C18—H18B109.5
C3—C4—C5112.04 (14)N1—C18—H18C109.5
O3—C4—C7105.20 (13)H18A—C18—H18C109.5
C3—C4—C7108.83 (15)H18B—C18—H18C109.5
C5—C4—C7113.98 (15)
(GF-NE2-1) top
Crystal data top
C36H39Cl2NO14F(000) = 1632
Mr = 780.58Dx = 1.437 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 9491 reflections
a = 8.6852 (17) Åθ = 2.0–31.0°
b = 15.047 (3) ŵ = 0.25 mm1
c = 27.605 (6) ÅT = 163 K
V = 3607.6 (13) Å3Block, colorless
Z = 40.33 × 0.33 × 0.22 mm
Data collection top
Rigaku Saturn 70 CCD area detector
diffractometer
8492 independent reflections
Radiation source: fine-focus sealed tube7628 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ω scansθmax = 28.3°, θmin = 1.5°
Absorption correction: multi-scan
R. H. Blessing, Acta Cryst. 1995 A51, 33-38
h = 1011
Tmin = 0.922, Tmax = 0.947k = 1320
15583 measured reflectionsl = 1636
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-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 reflectionsΔρmax = 0.21 e Å3
487 parametersΔρmin = 0.35 e Å3
0 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (5)
Crystal data top
C36H39Cl2NO14V = 3607.6 (13) Å3
Mr = 780.58Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.6852 (17) ŵ = 0.25 mm1
b = 15.047 (3) ÅT = 163 K
c = 27.605 (6) Å0.33 × 0.33 × 0.22 mm
Data collection top
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 = 0.947Rint = 0.029
15583 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.117Δρmax = 0.21 e Å3
S = 1.09Δρmin = 0.35 e Å3
8492 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
487 parametersAbsolute structure parameter: 0.01 (5)
0 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl2A0.25466 (7)0.93344 (5)0.79617 (2)0.02999 (14)
O6A0.91789 (19)0.95750 (13)0.84193 (7)0.0298 (4)
O4A0.9341 (2)0.85951 (14)0.74378 (7)0.0329 (4)
O2A0.6258 (2)0.95824 (13)0.67598 (7)0.0304 (4)
O3A0.52424 (19)0.85135 (12)0.74298 (6)0.0254 (4)
O5A0.3861 (2)1.02654 (13)0.87787 (7)0.0310 (4)
C10A0.6554 (3)0.99334 (18)0.86334 (10)0.0275 (5)
H10A0.68661.02540.89130.033*
C12A0.4471 (3)0.93905 (19)0.81133 (9)0.0269 (5)
C8A0.7160 (3)0.90503 (17)0.79335 (9)0.0247 (5)
C13A0.5581 (3)0.89865 (17)0.78322 (9)0.0237 (5)
C11A0.4983 (3)0.98695 (18)0.85148 (10)0.0267 (5)
C9A0.7641 (3)0.95289 (17)0.83424 (9)0.0253 (5)
O1A0.8484 (2)0.71295 (15)0.59465 (8)0.0429 (5)
C14A0.6835 (4)0.6777 (2)0.76273 (11)0.0377 (7)
H14E0.78370.69050.77740.057*
H14D0.67330.61340.75770.057*
H14F0.60130.69830.78430.057*
C2A0.7342 (3)0.8368 (2)0.63125 (10)0.0313 (6)
H2A0.73480.86950.60180.038*
C3A0.6765 (3)0.87440 (19)0.67148 (10)0.0273 (5)
C1A0.7960 (3)0.7466 (2)0.63186 (11)0.0317 (6)
C7A0.7968 (3)0.86436 (18)0.75331 (9)0.0255 (5)
C17A0.9707 (3)1.0122 (2)0.88150 (10)0.0338 (6)
H17D0.93581.07340.87660.051*
H17F1.08341.01080.88280.051*
H17E0.92870.98940.91200.051*
C5A0.6711 (3)0.72549 (18)0.71399 (10)0.0281 (5)
H5A0.57160.70730.69870.034*
C4A0.6685 (3)0.82677 (18)0.71964 (9)0.0244 (5)
C16A0.4312 (3)1.0837 (2)0.91734 (10)0.0335 (6)
H16E0.49341.04980.94050.050*
H16D0.33901.10650.93360.050*
H16F0.49171.13350.90470.050*
C15A0.6373 (4)1.0143 (2)0.63369 (11)0.0387 (7)
H15E0.74581.02180.62490.058*
H15F0.59191.07250.64080.058*
H15D0.58190.98670.60670.058*
C6A0.8011 (3)0.6985 (2)0.67950 (10)0.0331 (6)
H6AA0.90120.71060.69530.040*
H6AB0.79470.63380.67340.040*
Cl11.30892 (7)0.55221 (5)0.98757 (3)0.03578 (17)
O40.6228 (2)0.46365 (13)0.95249 (7)0.0323 (4)
O51.1873 (2)0.68532 (14)1.05221 (7)0.0349 (5)
C70.7606 (3)0.47843 (17)0.95503 (9)0.0262 (5)
O31.03089 (19)0.46104 (13)0.94255 (7)0.0275 (4)
O60.6493 (2)0.62105 (14)1.02196 (8)0.0332 (4)
O20.9426 (2)0.31530 (14)0.98710 (7)0.0327 (4)
C20.8043 (3)0.26401 (19)0.91760 (10)0.0296 (6)
H20.79770.20560.93050.035*
C100.9148 (3)0.65794 (19)1.03977 (10)0.0285 (5)
H100.88660.70211.06270.034*
O10.6744 (3)0.22285 (15)0.84724 (9)0.0469 (6)
C121.1166 (3)0.57592 (19)0.99705 (10)0.0286 (6)
C90.8019 (3)0.61001 (18)1.01572 (10)0.0273 (5)
C131.0020 (3)0.52884 (18)0.97396 (9)0.0249 (5)
C80.8456 (3)0.54368 (18)0.98230 (10)0.0270 (5)
C111.0707 (3)0.64114 (19)1.03028 (10)0.0295 (6)
C10.7369 (3)0.28192 (19)0.87093 (10)0.0321 (6)
C60.7398 (3)0.37619 (19)0.85215 (10)0.0311 (6)
H6A0.64180.40570.86080.037*
H6B0.74680.37480.81640.037*
C170.6005 (3)0.6832 (2)1.05876 (11)0.0358 (7)
H17A0.64060.66431.09030.054*
H17B0.48780.68491.05990.054*
H17C0.64000.74251.05100.054*
C30.8767 (3)0.32747 (18)0.94364 (10)0.0263 (5)
C50.8733 (3)0.43124 (19)0.87197 (10)0.0279 (5)
H60.97050.40590.85820.033*
C40.8834 (3)0.42301 (18)0.92743 (9)0.0257 (5)
C140.8626 (4)0.5272 (2)0.85524 (11)0.0398 (7)
H14A0.86930.52950.81980.060*
H14B0.94740.56150.86940.060*
H14C0.76410.55250.86570.060*
C150.9402 (4)0.2258 (2)1.00673 (11)0.0404 (7)
H15A0.83330.20671.01120.061*
H15B0.99360.22501.03800.061*
H15C0.99200.18530.98420.061*
C161.1494 (4)0.7501 (2)1.08890 (13)0.0458 (8)
H16A1.08940.79831.07430.069*
H16B1.24450.77431.10280.069*
H16C1.08880.72171.11450.069*
N10.2014 (3)0.71881 (17)0.82048 (10)0.0400 (6)
O80.3215 (3)0.73025 (17)0.84314 (9)0.0544 (7)
C180.2089 (3)0.71292 (19)0.76654 (10)0.0332 (6)
H18A0.30970.73530.75500.040*
H18B0.12690.75000.75200.040*
O70.0760 (3)0.71093 (19)0.83980 (10)0.0667 (8)
C190.1886 (5)0.6183 (2)0.75147 (13)0.0556 (10)
H19A0.26970.58180.76610.083*
H19B0.19500.61400.71610.083*
H19C0.08770.59690.76230.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl2A0.0218 (3)0.0329 (3)0.0352 (3)0.0015 (3)0.0007 (3)0.0039 (3)
O6A0.0205 (8)0.0384 (11)0.0304 (10)0.0018 (8)0.0028 (7)0.0076 (9)
O4A0.0222 (9)0.0424 (12)0.0341 (10)0.0003 (8)0.0005 (8)0.0058 (9)
O2A0.0363 (10)0.0281 (10)0.0269 (9)0.0021 (8)0.0019 (8)0.0033 (8)
O3A0.0230 (8)0.0296 (10)0.0236 (9)0.0002 (7)0.0007 (7)0.0053 (8)
O5A0.0269 (9)0.0363 (11)0.0299 (10)0.0044 (8)0.0016 (8)0.0072 (8)
C10A0.0262 (12)0.0298 (13)0.0264 (12)0.0022 (10)0.0001 (10)0.0030 (11)
C12A0.0226 (11)0.0298 (14)0.0284 (12)0.0026 (11)0.0004 (10)0.0011 (11)
C8A0.0260 (12)0.0240 (12)0.0242 (11)0.0011 (10)0.0011 (10)0.0016 (10)
C13A0.0241 (12)0.0240 (12)0.0229 (12)0.0000 (10)0.0008 (10)0.0014 (10)
C11A0.0249 (12)0.0279 (13)0.0273 (13)0.0040 (10)0.0028 (10)0.0006 (11)
C9A0.0213 (11)0.0267 (12)0.0279 (12)0.0009 (10)0.0011 (10)0.0002 (10)
O1A0.0397 (11)0.0500 (14)0.0388 (12)0.0068 (10)0.0130 (10)0.0160 (11)
C14A0.0430 (16)0.0356 (16)0.0346 (15)0.0039 (14)0.0011 (14)0.0000 (13)
C2A0.0316 (14)0.0382 (15)0.0242 (12)0.0066 (12)0.0024 (11)0.0013 (11)
C3A0.0258 (12)0.0294 (14)0.0267 (12)0.0013 (11)0.0036 (11)0.0022 (11)
C1A0.0222 (12)0.0394 (15)0.0336 (14)0.0067 (11)0.0049 (11)0.0102 (12)
C7A0.0252 (12)0.0255 (12)0.0258 (12)0.0011 (10)0.0005 (10)0.0020 (10)
C17A0.0268 (13)0.0448 (17)0.0299 (14)0.0068 (12)0.0025 (11)0.0087 (13)
C5A0.0280 (13)0.0270 (13)0.0292 (13)0.0017 (11)0.0024 (11)0.0022 (11)
C4A0.0210 (11)0.0281 (13)0.0242 (12)0.0024 (10)0.0011 (10)0.0030 (10)
C16A0.0374 (15)0.0359 (15)0.0271 (13)0.0044 (13)0.0002 (12)0.0074 (12)
C15A0.0433 (16)0.0368 (16)0.0360 (16)0.0091 (13)0.0056 (13)0.0095 (13)
C6A0.0281 (13)0.0374 (15)0.0337 (14)0.0030 (12)0.0014 (12)0.0066 (13)
Cl10.0221 (3)0.0506 (4)0.0346 (3)0.0017 (3)0.0003 (3)0.0093 (3)
O40.0220 (9)0.0375 (11)0.0374 (11)0.0007 (8)0.0023 (8)0.0063 (9)
O50.0287 (9)0.0398 (11)0.0363 (11)0.0086 (9)0.0003 (9)0.0132 (9)
C70.0233 (11)0.0275 (12)0.0279 (12)0.0014 (10)0.0027 (10)0.0018 (10)
O30.0216 (8)0.0325 (10)0.0284 (9)0.0019 (7)0.0011 (7)0.0081 (8)
O60.0261 (9)0.0360 (11)0.0375 (11)0.0028 (8)0.0027 (8)0.0116 (9)
O20.0398 (11)0.0325 (11)0.0259 (9)0.0020 (9)0.0062 (9)0.0003 (9)
C20.0271 (12)0.0322 (14)0.0295 (13)0.0013 (11)0.0005 (11)0.0028 (11)
C100.0268 (12)0.0308 (14)0.0279 (13)0.0007 (11)0.0003 (11)0.0050 (11)
O10.0562 (14)0.0404 (12)0.0441 (13)0.0126 (11)0.0143 (11)0.0071 (11)
C120.0232 (12)0.0347 (14)0.0278 (13)0.0030 (11)0.0002 (10)0.0032 (11)
C90.0275 (12)0.0259 (13)0.0285 (12)0.0012 (10)0.0003 (11)0.0005 (11)
C130.0243 (12)0.0261 (13)0.0244 (12)0.0000 (10)0.0006 (10)0.0040 (10)
C80.0231 (12)0.0315 (14)0.0265 (12)0.0011 (10)0.0036 (10)0.0012 (11)
C110.0273 (13)0.0316 (14)0.0297 (13)0.0073 (11)0.0020 (11)0.0027 (12)
C10.0318 (14)0.0334 (14)0.0312 (14)0.0019 (12)0.0013 (12)0.0060 (12)
C60.0306 (13)0.0332 (14)0.0295 (13)0.0019 (12)0.0074 (12)0.0038 (11)
C170.0309 (14)0.0374 (16)0.0392 (16)0.0056 (12)0.0045 (13)0.0140 (14)
C30.0247 (12)0.0300 (13)0.0242 (12)0.0032 (10)0.0007 (10)0.0003 (11)
C50.0267 (12)0.0314 (13)0.0255 (12)0.0006 (11)0.0012 (10)0.0003 (11)
C40.0225 (11)0.0284 (13)0.0262 (12)0.0026 (10)0.0033 (10)0.0048 (11)
C140.0483 (17)0.0378 (16)0.0333 (15)0.0023 (14)0.0019 (13)0.0050 (13)
C150.0520 (18)0.0369 (17)0.0323 (15)0.0073 (14)0.0039 (14)0.0056 (13)
C160.0429 (17)0.0476 (19)0.0468 (19)0.0098 (15)0.0003 (15)0.0243 (16)
N10.0523 (16)0.0303 (13)0.0373 (14)0.0088 (12)0.0004 (13)0.0023 (11)
O80.0690 (16)0.0469 (14)0.0472 (14)0.0061 (13)0.0217 (13)0.0057 (12)
C180.0381 (15)0.0292 (14)0.0325 (14)0.0003 (12)0.0001 (12)0.0016 (12)
O70.0750 (18)0.0679 (19)0.0573 (17)0.0324 (15)0.0252 (15)0.0161 (15)
C190.096 (3)0.0287 (16)0.0421 (18)0.0017 (18)0.003 (2)0.0030 (14)
Geometric parameters (Å, º) top
Cl2A—C12A1.725 (3)C7—C41.554 (4)
O6A—C9A1.355 (3)O3—C131.362 (3)
O6A—C17A1.442 (3)O3—C41.464 (3)
O4A—C7A1.223 (3)O6—C91.347 (3)
O2A—C3A1.342 (3)O6—C171.444 (3)
O2A—C15A1.444 (3)O2—C31.342 (3)
O3A—C13A1.352 (3)O2—C151.452 (4)
O3A—C4A1.457 (3)C2—C31.351 (4)
O5A—C11A1.355 (3)C2—C11.441 (4)
O5A—C16A1.442 (3)C2—H20.9500
C10A—C9A1.381 (4)C10—C91.387 (4)
C10A—C11A1.406 (3)C10—C111.402 (4)
C10A—H10A0.9500C10—H100.9500
C12A—C13A1.379 (4)O1—C11.230 (3)
C12A—C11A1.395 (4)C12—C131.378 (4)
C8A—C9A1.402 (3)C12—C111.401 (4)
C8A—C13A1.403 (3)C9—C81.411 (4)
C8A—C7A1.445 (4)C13—C81.396 (3)
O1A—C1A1.233 (3)C1—C61.511 (4)
C14A—C5A1.530 (4)C6—C51.527 (4)
C14A—H14E0.9800C6—H6A0.9900
C14A—H14D0.9800C6—H6B0.9900
C14A—H14F0.9800C17—H17A0.9800
C2A—C3A1.344 (4)C17—H17B0.9800
C2A—C1A1.459 (4)C17—H17C0.9800
C2A—H2A0.9500C3—C41.507 (4)
C3A—C4A1.512 (4)C5—C141.519 (4)
C1A—C6A1.502 (4)C5—C41.539 (4)
C7A—C4A1.557 (4)C5—H61.0000
C17A—H17D0.9800C14—H14A0.9800
C17A—H17F0.9800C14—H14B0.9800
C17A—H17E0.9800C14—H14C0.9800
C5A—C6A1.532 (4)C15—H15A0.9800
C5A—C4A1.532 (4)C15—H15B0.9800
C5A—H5A1.0000C15—H15C0.9800
C16A—H16E0.9800C16—H16A0.9800
C16A—H16D0.9800C16—H16B0.9800
C16A—H16F0.9800C16—H16C0.9800
C15A—H15E0.9800N1—O71.218 (4)
C15A—H15F0.9800N1—O81.228 (4)
C15A—H15D0.9800N1—C181.493 (4)
C6A—H6AA0.9900C18—C191.494 (4)
C6A—H6AB0.9900C18—H18A0.9900
Cl1—C121.728 (3)C18—H18B0.9900
O4—C71.219 (3)C19—H19A0.9800
O5—C111.354 (3)C19—H19B0.9800
O5—C161.444 (4)C19—H19C0.9800
C7—C81.441 (4)
C9A—O6A—C17A117.5 (2)C3—C2—H2118.9
C3A—O2A—C15A116.9 (2)C1—C2—H2118.9
C13A—O3A—C4A108.06 (19)C9—C10—C11120.0 (3)
C11A—O5A—C16A118.2 (2)C9—C10—H10120.0
C9A—C10A—C11A119.8 (3)C11—C10—H10120.0
C9A—C10A—H10A120.1C13—C12—C11117.2 (2)
C11A—C10A—H10A120.1C13—C12—Cl1121.5 (2)
C13A—C12A—C11A116.9 (2)C11—C12—Cl1121.2 (2)
C13A—C12A—Cl2A121.3 (2)O6—C9—C10124.8 (2)
C11A—C12A—Cl2A121.8 (2)O6—C9—C8115.8 (2)
C9A—C8A—C13A119.1 (2)C10—C9—C8119.4 (2)
C9A—C8A—C7A133.5 (2)O3—C13—C12123.1 (2)
C13A—C8A—C7A107.1 (2)O3—C13—C8113.8 (2)
O3A—C13A—C12A122.9 (2)C12—C13—C8123.0 (2)
O3A—C13A—C8A114.3 (2)C13—C8—C9118.8 (2)
C12A—C13A—C8A122.7 (2)C13—C8—C7107.7 (2)
O5A—C11A—C12A115.2 (2)C9—C8—C7133.3 (2)
O5A—C11A—C10A122.9 (2)O5—C11—C12115.1 (2)
C12A—C11A—C10A122.0 (2)O5—C11—C10123.4 (3)
O6A—C9A—C10A124.1 (2)C12—C11—C10121.5 (2)
O6A—C9A—C8A116.5 (2)O1—C1—C2121.3 (3)
C10A—C9A—C8A119.4 (2)O1—C1—C6120.2 (3)
C5A—C14A—H14E109.5C2—C1—C6118.4 (2)
C5A—C14A—H14D109.5C1—C6—C5113.5 (2)
H14E—C14A—H14D109.5C1—C6—H6A108.9
C5A—C14A—H14F109.5C5—C6—H6A108.9
H14E—C14A—H14F109.5C1—C6—H6B108.9
H14D—C14A—H14F109.5C5—C6—H6B108.9
C3A—C2A—C1A121.3 (3)H6A—C6—H6B107.7
C3A—C2A—H2A119.3O6—C17—H17A109.5
C1A—C2A—H2A119.3O6—C17—H17B109.5
O2A—C3A—C2A126.5 (3)H17A—C17—H17B109.5
O2A—C3A—C4A110.4 (2)O6—C17—H17C109.5
C2A—C3A—C4A123.0 (3)H17A—C17—H17C109.5
O1A—C1A—C2A120.6 (3)H17B—C17—H17C109.5
O1A—C1A—C6A121.4 (3)O2—C3—C2125.3 (3)
C2A—C1A—C6A118.0 (2)O2—C3—C4112.3 (2)
O4A—C7A—C8A131.6 (3)C2—C3—C4122.3 (2)
O4A—C7A—C4A123.2 (2)C14—C5—C6111.1 (2)
C8A—C7A—C4A105.2 (2)C14—C5—C4112.5 (2)
O6A—C17A—H17D109.5C6—C5—C4110.9 (2)
O6A—C17A—H17F109.5C14—C5—H6107.4
H17D—C17A—H17F109.5C6—C5—H6107.4
O6A—C17A—H17E109.5C4—C5—H6107.4
H17D—C17A—H17E109.5O3—C4—C3108.8 (2)
H17F—C17A—H17E109.5O3—C4—C5107.6 (2)
C14A—C5A—C6A111.7 (2)C3—C4—C5111.7 (2)
C14A—C5A—C4A112.3 (2)O3—C4—C7104.5 (2)
C6A—C5A—C4A109.7 (2)C3—C4—C7109.9 (2)
C14A—C5A—H5A107.6C5—C4—C7113.9 (2)
C6A—C5A—H5A107.6C5—C14—H14A109.5
C4A—C5A—H5A107.6C5—C14—H14B109.5
O3A—C4A—C3A107.9 (2)H14A—C14—H14B109.5
O3A—C4A—C5A108.1 (2)C5—C14—H14C109.5
C3A—C4A—C5A112.4 (2)H14A—C14—H14C109.5
O3A—C4A—C7A105.0 (2)H14B—C14—H14C109.5
C3A—C4A—C7A108.7 (2)O2—C15—H15A109.5
C5A—C4A—C7A114.3 (2)O2—C15—H15B109.5
O5A—C16A—H16E109.5H15A—C15—H15B109.5
O5A—C16A—H16D109.5O2—C15—H15C109.5
H16E—C16A—H16D109.5H15A—C15—H15C109.5
O5A—C16A—H16F109.5H15B—C15—H15C109.5
H16E—C16A—H16F109.5O5—C16—H16A109.5
H16D—C16A—H16F109.5O5—C16—H16B109.5
O2A—C15A—H15E109.5H16A—C16—H16B109.5
O2A—C15A—H15F109.5O5—C16—H16C109.5
H15E—C15A—H15F109.5H16A—C16—H16C109.5
O2A—C15A—H15D109.5H16B—C16—H16C109.5
H15E—C15A—H15D109.5O7—N1—O8123.3 (3)
H15F—C15A—H15D109.5O7—N1—C18118.0 (3)
C1A—C6A—C5A113.2 (2)O8—N1—C18118.6 (3)
C1A—C6A—H6AA108.9N1—C18—C19109.2 (3)
C5A—C6A—H6AA108.9N1—C18—H18A109.8
C1A—C6A—H6AB108.9C19—C18—H18A109.8
C5A—C6A—H6AB108.9N1—C18—H18B109.8
H6AA—C6A—H6AB107.7C19—C18—H18B109.8
C11—O5—C16118.4 (2)H18A—C18—H18B108.3
O4—C7—C8131.1 (3)C18—C19—H19A109.5
O4—C7—C4123.2 (2)C18—C19—H19B109.5
C8—C7—C4105.7 (2)H19A—C19—H19B109.5
C13—O3—C4108.25 (19)C18—C19—H19C109.5
C9—O6—C17117.3 (2)H19A—C19—H19C109.5
C3—O2—C15117.0 (2)H19B—C19—H19C109.5
C3—C2—C1122.2 (3)
(GF-NE1-1) top
Crystal data top
C19H22ClNO8F(000) = 896
Mr = 427.83Dx = 1.432 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 2981 reflections
a = 21.931 (4) Åθ = 2.1–31.0°
b = 8.6541 (17) ŵ = 0.24 mm1
c = 11.797 (2) ÅT = 110 K
β = 117.57 (3)°Block, colorless
V = 1984.7 (8) Å30.44 × 0.44 × 0.44 mm
Z = 4
Data collection top
Rigaku Saturn 70 CCD area detector
diffractometer
4634 independent reflections
Radiation source: fine-focus sealed tube4497 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
ω scansθmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan
R. H. Blessing, Acta Cryst. 1995 A51, 33-38
h = 2926
Tmin = 0.910, Tmax = 0.910k = 1111
7580 measured reflectionsl = 1515
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.09Δρmax = 0.43 e Å3
4634 reflectionsΔρmin = 0.33 e Å3
222 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0027 (6)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.03 (6)
Crystal data top
C19H22ClNO8V = 1984.7 (8) Å3
Mr = 427.83Z = 4
Monoclinic, C2Mo Kα radiation
a = 21.931 (4) ŵ = 0.24 mm1
b = 8.6541 (17) ÅT = 110 K
c = 11.797 (2) Å0.44 × 0.44 × 0.44 mm
β = 117.57 (3)°
Data collection top
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 = 0.910Rint = 0.016
7580 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.119Δρmax = 0.43 e Å3
S = 1.09Δρmin = 0.33 e Å3
4634 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
222 parametersAbsolute structure parameter: 0.03 (6)
1 restraint
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.82785 (2)0.35650 (6)0.90574 (4)0.02756 (12)
O80.85329 (8)0.32212 (18)0.77080 (14)0.0278 (3)
O70.83918 (8)0.08887 (17)0.75312 (13)0.0246 (3)
O60.72964 (8)0.05097 (19)0.57020 (14)0.0301 (3)
C100.83478 (10)0.0471 (2)1.08388 (18)0.0229 (4)
H100.83360.07991.15970.027*
O90.82446 (8)0.22128 (17)1.12859 (14)0.0282 (3)
C90.84110 (9)0.1554 (2)1.00308 (17)0.0220 (4)
C110.83018 (10)0.1099 (2)1.05369 (18)0.0218 (4)
C130.83719 (10)0.0521 (2)0.86316 (18)0.0211 (4)
O100.84719 (8)0.31013 (16)1.02326 (13)0.0241 (3)
C70.84864 (10)0.1843 (2)0.78915 (18)0.0223 (4)
C120.83167 (10)0.1632 (2)0.94278 (19)0.0221 (4)
C40.84967 (10)0.0541 (2)0.69879 (18)0.0231 (4)
C30.78913 (11)0.0771 (2)0.56805 (19)0.0253 (4)
C50.91826 (11)0.0387 (3)0.69502 (19)0.0283 (4)
H50.91810.06420.65640.034*
C170.85378 (12)0.3655 (3)1.14331 (18)0.0280 (4)
H17A0.89280.31431.21360.042*
H17B0.81150.34261.14900.042*
H17C0.86150.47751.14910.042*
C80.84141 (10)0.1051 (2)0.89023 (18)0.0236 (4)
C160.81688 (13)0.1753 (3)1.2390 (2)0.0334 (5)
H16A0.77660.10811.21200.050*
H16B0.85810.11941.29890.050*
H16C0.81080.26741.28110.050*
O50.87189 (12)0.1927 (3)0.38399 (19)0.0582 (6)
C20.79711 (12)0.1264 (3)0.46686 (19)0.0343 (5)
H20.75750.13900.38650.041*
C140.98022 (12)0.0409 (3)0.8294 (2)0.0393 (5)
H14A0.98820.14670.86280.059*
H14B1.02120.00350.82470.059*
H14C0.97080.02630.88630.059*
C60.92521 (12)0.1607 (3)0.6091 (2)0.0333 (5)
H6A0.92930.26370.64840.040*
H6B0.96780.14130.60200.040*
C150.66728 (11)0.0811 (3)0.4539 (2)0.0353 (5)
H15A0.66230.00420.38920.053*
H15B0.66950.18470.42250.053*
H15C0.62770.07480.47110.053*
C10.86483 (14)0.1610 (3)0.4775 (2)0.0381 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0323 (2)0.0170 (2)0.0308 (2)0.00179 (18)0.01245 (18)0.00069 (18)
O80.0418 (8)0.0195 (7)0.0268 (7)0.0075 (6)0.0199 (6)0.0023 (6)
O70.0324 (7)0.0207 (7)0.0221 (6)0.0001 (5)0.0138 (6)0.0002 (5)
O60.0297 (7)0.0312 (8)0.0266 (7)0.0021 (6)0.0107 (6)0.0034 (6)
C100.0257 (8)0.0244 (10)0.0192 (8)0.0008 (7)0.0109 (7)0.0017 (7)
O90.0374 (8)0.0206 (7)0.0292 (7)0.0014 (6)0.0175 (6)0.0053 (6)
C90.0254 (8)0.0175 (9)0.0236 (8)0.0001 (7)0.0117 (6)0.0022 (8)
C110.0207 (8)0.0216 (10)0.0221 (8)0.0005 (7)0.0089 (7)0.0050 (7)
C130.0236 (8)0.0192 (9)0.0200 (8)0.0007 (7)0.0096 (7)0.0022 (7)
O100.0410 (8)0.0145 (7)0.0215 (6)0.0009 (5)0.0186 (6)0.0004 (5)
C70.0290 (9)0.0197 (9)0.0212 (8)0.0032 (7)0.0141 (7)0.0004 (6)
C120.0248 (8)0.0157 (9)0.0267 (8)0.0000 (7)0.0128 (7)0.0023 (7)
C40.0298 (9)0.0194 (9)0.0208 (8)0.0005 (7)0.0124 (7)0.0007 (7)
C30.0308 (9)0.0201 (9)0.0242 (9)0.0005 (7)0.0120 (7)0.0020 (7)
C50.0299 (9)0.0321 (11)0.0246 (9)0.0055 (8)0.0141 (8)0.0070 (8)
C170.0410 (11)0.0256 (10)0.0207 (8)0.0020 (8)0.0171 (8)0.0010 (7)
C80.0279 (8)0.0212 (10)0.0231 (8)0.0005 (7)0.0131 (7)0.0004 (6)
C160.0463 (12)0.0290 (12)0.0272 (10)0.0067 (9)0.0189 (9)0.0029 (8)
O50.0671 (13)0.0784 (18)0.0367 (9)0.0186 (11)0.0304 (10)0.0053 (10)
C20.0391 (10)0.0374 (13)0.0223 (8)0.0015 (10)0.0108 (8)0.0017 (9)
C140.0300 (10)0.0539 (16)0.0311 (11)0.0008 (10)0.0117 (9)0.0075 (11)
C60.0396 (11)0.0347 (13)0.0320 (10)0.0102 (10)0.0219 (9)0.0072 (9)
C150.0291 (10)0.0380 (12)0.0322 (10)0.0007 (9)0.0085 (8)0.0050 (9)
C10.0508 (12)0.0383 (14)0.0308 (10)0.0102 (11)0.0236 (10)0.0009 (10)
Geometric parameters (Å, º) top
Cl1—C121.721 (2)C5—C61.519 (3)
O8—C71.225 (2)C5—C141.538 (3)
O7—C131.357 (2)C5—H51.0000
O7—C41.460 (2)C17—H17A0.9800
O6—C31.336 (3)C17—H17B0.9800
O6—C151.443 (3)C17—H17C0.9800
C10—C91.389 (3)C16—H16A0.9800
C10—C111.397 (3)C16—H16B0.9800
C10—H100.9500C16—H16C0.9800
O9—C111.352 (2)O5—C11.214 (3)
O9—C161.443 (3)C2—C11.462 (3)
C9—O101.356 (2)C2—H20.9500
C9—C81.404 (2)C14—H14A0.9800
C11—C121.402 (3)C14—H14B0.9800
C13—C121.389 (3)C14—H14C0.9800
C13—C81.390 (3)C6—C11.503 (3)
O10—C171.438 (2)C6—H6A0.9900
C7—C81.446 (3)C6—H6B0.9900
C7—C41.558 (3)C15—H15A0.9800
C4—C31.512 (3)C15—H15B0.9800
C4—C51.531 (3)C15—H15C0.9800
C3—C21.353 (3)
C13—O7—C4107.60 (15)O10—C17—H17B109.5
C3—O6—C15117.10 (18)H17A—C17—H17B109.5
C9—C10—C11119.99 (17)O10—C17—H17C109.5
C9—C10—H10120.0H17A—C17—H17C109.5
C11—C10—H10120.0H17B—C17—H17C109.5
C11—O9—C16118.55 (17)C13—C8—C9119.48 (18)
O10—C9—C10125.37 (17)C13—C8—C7107.16 (17)
O10—C9—C8115.43 (17)C9—C8—C7133.30 (19)
C10—C9—C8119.20 (19)O9—C16—H16A109.5
O9—C11—C10122.99 (18)O9—C16—H16B109.5
O9—C11—C12115.13 (18)H16A—C16—H16B109.5
C10—C11—C12121.88 (17)O9—C16—H16C109.5
O7—C13—C12122.41 (18)H16A—C16—H16C109.5
O7—C13—C8114.92 (16)H16B—C16—H16C109.5
C12—C13—C8122.68 (18)C3—C2—C1121.98 (19)
C9—O10—C17117.33 (15)C3—C2—H2119.0
O8—C7—C8131.05 (18)C1—C2—H2119.0
O8—C7—C4123.67 (17)C5—C14—H14A109.5
C8—C7—C4105.28 (16)C5—C14—H14B109.5
C13—C12—C11116.76 (18)H14A—C14—H14B109.5
C13—C12—Cl1120.73 (15)C5—C14—H14C109.5
C11—C12—Cl1122.51 (15)H14A—C14—H14C109.5
O7—C4—C3108.48 (16)H14B—C14—H14C109.5
O7—C4—C5107.19 (16)C1—C6—C5112.19 (18)
C3—C4—C5113.12 (16)C1—C6—H6A109.2
O7—C4—C7104.90 (14)C5—C6—H6A109.2
C3—C4—C7108.59 (16)C1—C6—H6B109.2
C5—C4—C7114.10 (16)C5—C6—H6B109.2
O6—C3—C2126.60 (19)H6A—C6—H6B107.9
O6—C3—C4111.27 (17)O6—C15—H15A109.5
C2—C3—C4122.03 (19)O6—C15—H15B109.5
C6—C5—C4111.24 (18)H15A—C15—H15B109.5
C6—C5—C14111.46 (19)O6—C15—H15C109.5
C4—C5—C14112.34 (17)H15A—C15—H15C109.5
C6—C5—H5107.2H15B—C15—H15C109.5
C4—C5—H5107.2O5—C1—C2121.3 (2)
C14—C5—H5107.2O5—C1—C6121.1 (2)
O10—C17—H17A109.5C2—C1—C6117.56 (18)

Experimental details

(GF-MeCN)(GF-NM)(GF-NE2-1)(GF-NE1-1)
Crystal data
Chemical formulaC19H20ClNO6C18H20ClNO8C36H39Cl2NO14C19H22ClNO8
Mr393.81413.80780.58427.83
Crystal system, space groupMonoclinic, P21Orthorhombic, P212121Orthorhombic, P212121Monoclinic, C2
Temperature (K)110110163110
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), 9090, 90, 9090, 90, 9090, 117.57 (3), 90
V3)1930.8 (7)1933.2 (6)3607.6 (13)1984.7 (8)
Z4444
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.230.240.250.24
Crystal size (mm)0.33 × 0.22 × 0.220.44 × 0.33 × 0.220.33 × 0.33 × 0.220.44 × 0.44 × 0.44
Data collection
DiffractometerRigaku 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 correctionMulti-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, Tmax0.927, 0.9510.900, 0.9480.922, 0.9470.910, 0.910
No. of measured, independent and
observed [I > 2σ(I)] reflections
27812, 8585, 8103 15653, 4791, 4703 15583, 8492, 7628 7580, 4634, 4497
Rint0.0300.0260.0290.016
(sin θ/λ)max1)0.6670.6670.6660.667
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 reflections8585479184924634
No. of parameters497258487222
No. of restraints1001
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.72, 0.380.28, 0.330.21, 0.350.43, 0.33
Absolute structureFlack H D (1983), Acta Cryst. A39, 876-881Flack H D (1983), Acta Cryst. A39, 876-881Flack H D (1983), Acta Cryst. A39, 876-881Flack H D (1983), Acta Cryst. A39, 876-881
Absolute structure parameter0.05 (5)0.02 (6)0.01 (5)0.03 (6)

Computer programs: CrystalClear (Rigaku Inc., 2007), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997).

 

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