Download citation
Download citation
link to html
The compounds analysed are the O,O′-dibenzoyl derivatives of (R,R)-tartaric acid, asymmetrically substituted by ester, amide and nitrile groups. Benzoylation does not introduce drastic changes to the molecular conformation. All investigated molecules adopt the planar T conformation of the four-carbon chain with noticeably smaller departures from the ideal conformation than observed in the nonbenzoylated analogs. Primary and secondary amides always orient the C=O bond antiperiplanar (a) with respect to the nearest C*—O bond, while methylester groups adjust their conformation to that adopted by the amide substituent situated at the other end of the molecule. Tertiary amides and carboxyl groups place their carbonyls at the same side as the nearest C*—O bond (the s form), but often deviations from coplanarity of the two bonds are significant and higher than those observed in the nonbenzoylated series. The results presented demonstrate the importance of dipole/dipole interactions between CO and βC*H groups in stabilizing the molecular conformation, and between carbonyl groups in stabilizing crystal packing of the molecules that lack classical hydrogen-bond donor groups. An illustration is provided as to how a small change in mutual orientation of molecules arranged in a close-packed fashion causes a change in the character of intermolecular interactions from van der Waals to sandwich stacking between the benzoyloxy phenyls, and to dipolar between the benzoyloxy carbonyls. Hydrogen-bonded molecules tend to orient in a head-to-tail mode; the head-to-head arrangement being limited to cases in which terminal carbonyl groups are situated at one side of the molecule. The orientation of the benzoyloxy substituents with respect to the carbon main chain is such that the (O=)C—O—C—H bond system often deviates significantly from planarity.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010876810100430X/na0118sup1.cif
Contains datablocks boh1, boh2, boh3, bn13, bn23, bom1, bom3, bcn3, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810100430X/na0118boh1sup2.hkl
Contains datablock boh1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810100430X/na0118boh2sup3.hkl
Contains datablock boh2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810100430X/na0118boh3sup4.hkl
Contains datablock boh3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810100430X/na0118bn13sup5.hkl
Contains datablock bn13

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810100430X/na0118bn23sup6.hkl
Contains datablock bn23

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810100430X/na0118bom1sup7.hkl
Contains datablock bom1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810100430X/na0118bom3sup8.hkl
Contains datablock nom2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810100430X/na0118bcn3sup9.hkl
Contains datablock bcn3

CCDC references: 166522; 166523; 166524; 166525; 166526; 166527; 166528; 166529

Computing details top

Data collection: Kuma KM4CCD software (Kuma Diffraction, 1999) for boh1, boh3, bn13; Kuma KM-4 Software (Kuma Diffraction, 1991) for boh2, bn23, bom1, bom3; SYNTEX Operation Manual for bcn3. Cell refinement: Kuma KM4CCD software for boh1, boh3, bn13; Kuma KM-4 Software for boh2; Kuma KM-4 Software (Kuma Diffraction, 1991) for bn23, bom1, bom3; SYNTEX XTL Operation Manual for bcn3. Data reduction: Kuma KM4CCD software for boh1, boh3, bn13; Kuma KM-4 Software for boh2; Kuma KM-4 Software (Kuma Diffraction, 1991) for bn23, bom1, bom3; PRARA for bcn3. For all compounds, program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Simens Analytical X-Ray Instruments (1989); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
(boh1) (R,R)-(-)-O,O'-Dibenzoyltartaric acid monoamide top
Crystal data top
(C18H15NO7)·0.15(H2O)Z = 4
Mr = 360.01F(000) = 750
Monoclinic, P21Dx = 1.345 Mg m3
a = 7.3930 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 19.950 (1) ŵ = 0.11 mm1
c = 12.1630 (6) ÅT = 120 K
β = 97.770 (4)°Prism, colourless
V = 1777.45 (16) Å30.25 × 0.20 × 0.20 mm
Data collection top
Kuma KM4CCD κ-geometry
diffractometer
2463 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.047
Graphite monochromatorθmax = 27.5°, θmin = 4.1°
ω scansh = 96
11340 measured reflectionsk = 2225
4144 independent reflectionsl = 1415
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)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.072Calculated w = 1/[σ2(Fo2) + (0.0337P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.84(Δ/σ)max < 0.001
4144 reflectionsΔρmax = 0.15 e Å3
489 parametersΔρmin = 0.16 e Å3
13 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods
Crystal data top
(C18H15NO7)·0.15(H2O)V = 1777.45 (16) Å3
Mr = 360.01Z = 4
Monoclinic, P21Mo Kα radiation
a = 7.3930 (4) ŵ = 0.11 mm1
b = 19.950 (1) ÅT = 120 K
c = 12.1630 (6) Å0.25 × 0.20 × 0.20 mm
β = 97.770 (4)°
Data collection top
Kuma KM4CCD κ-geometry
diffractometer
2463 reflections with I > 2σ(I)
11340 measured reflectionsRint = 0.047
4144 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03813 restraints
wR(F2) = 0.072H atoms treated by a mixture of independent and constrained refinement
S = 0.84Δρmax = 0.15 e Å3
4144 reflectionsΔρmin = 0.16 e Å3
489 parametersAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
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*/UeqOcc. (<1)
C10.4587 (4)0.49114 (15)0.4556 (3)0.0302 (7)
C20.6632 (4)0.50111 (15)0.4608 (2)0.0275 (7)
H20.70300.53600.51300.033*
C30.7652 (4)0.43642 (14)0.4948 (2)0.0272 (7)
H30.75840.42730.57180.033*
C40.9638 (4)0.44468 (15)0.4781 (2)0.0272 (7)
C200.6433 (4)0.58012 (15)0.3175 (2)0.0305 (7)
C210.7085 (4)0.60169 (17)0.2144 (2)0.0335 (7)
C220.6695 (4)0.66748 (18)0.1797 (3)0.0389 (8)
H220.59470.69540.21950.047*
C230.7407 (5)0.69266 (19)0.0877 (3)0.0503 (10)
H230.71610.73810.06410.060*
C240.8472 (5)0.6520 (2)0.0302 (3)0.0509 (10)
H240.89790.66900.03300.061*
C250.8825 (5)0.5861 (2)0.0628 (3)0.0528 (10)
H250.95510.55780.02200.063*
C260.8125 (4)0.56069 (17)0.1552 (3)0.0408 (8)
H260.83720.51520.17860.049*
C300.5861 (3)0.33600 (14)0.4786 (2)0.0255 (6)
C310.5094 (3)0.28404 (14)0.3997 (2)0.0245 (6)
C320.5026 (4)0.21836 (15)0.4367 (3)0.0322 (7)
H320.54390.20780.51310.039*
C330.4358 (4)0.16848 (16)0.3648 (3)0.0365 (8)
H330.43730.12270.38980.044*
C340.3690 (4)0.18388 (16)0.2552 (3)0.0361 (8)
H340.31880.14920.20540.043*
C350.3714 (4)0.24930 (16)0.2192 (3)0.0356 (8)
H350.32420.26000.14370.043*
C360.4451 (4)0.29985 (15)0.2893 (2)0.0308 (7)
H360.45000.34520.26310.037*
O10.3641 (3)0.47297 (11)0.37253 (17)0.0404 (6)
O20.7092 (2)0.51889 (9)0.35325 (15)0.0291 (5)
O30.6861 (2)0.38145 (10)0.42845 (14)0.0280 (5)
O41.0549 (2)0.48690 (10)0.53853 (16)0.0327 (5)
O100.4031 (3)0.50124 (10)0.55265 (16)0.0329 (5)
H100.285 (5)0.4947 (19)0.550 (3)0.066 (12)*
O200.5478 (3)0.61289 (10)0.37096 (16)0.0393 (5)
O300.5663 (3)0.33970 (10)0.57551 (16)0.0347 (5)
N41.0266 (3)0.40846 (12)0.40109 (19)0.0312 (6)
H411.14340.41260.38840.037*
H420.95190.37900.36130.037*
C1'1.0331 (8)0.3726 (3)1.0028 (4)0.0361 (14)0.70
C1A0.9993 (15)0.3794 (6)1.0410 (9)0.022 (3)*0.30
C2'0.8161 (4)0.37228 (16)1.0079 (3)0.0461 (9)
H2'0.78130.40451.06000.055*
C3'0.7230 (4)0.38591 (16)0.8905 (2)0.0382 (8)
H3'0.77470.42600.86370.046*
C4'0.5171 (4)0.39527 (15)0.8856 (3)0.0365 (8)
C20'0.8211 (4)0.28412 (17)1.1394 (3)0.0375 (8)
C21'0.7962 (4)0.21125 (16)1.1512 (3)0.0338 (7)
C22'0.8688 (4)0.18095 (19)1.2506 (3)0.0431 (8)
H22'0.92810.20781.31050.052*
C23'0.8527 (5)0.1125 (2)1.2624 (3)0.0517 (10)
H23'0.90890.09131.32940.062*
C24'0.7659 (5)0.07369 (19)1.1777 (3)0.0506 (9)
H24'0.75290.02621.18740.061*
C25'0.6907 (5)0.10348 (18)1.0793 (3)0.0466 (9)
H25'0.62850.07681.02000.056*
C26'0.7068 (4)0.17220 (17)1.0653 (3)0.0406 (8)
H26'0.65650.19250.99620.049*
C30'0.9030 (5)0.33526 (18)0.7610 (3)0.0429 (8)
C31'0.9292 (4)0.27327 (17)0.6987 (3)0.0375 (8)
C32'1.0420 (4)0.2766 (2)0.6149 (3)0.0518 (10)
H32'1.10310.31780.60210.062*
C33'1.0675 (5)0.2202 (3)0.5525 (3)0.0638 (12)
H33'1.14180.22210.49350.077*
C34'0.9836 (5)0.1608 (3)0.5740 (3)0.0641 (12)
H34'1.00050.12170.53040.077*
C35'0.8740 (5)0.1570 (2)0.6572 (3)0.0529 (10)
H35'0.81750.11540.67320.063*
C36'0.8450 (4)0.21371 (18)0.7195 (3)0.0411 (8)
H36'0.76780.21180.77700.049*
O1'1.1181 (6)0.3216 (2)1.0027 (4)0.0415 (11)0.70
O1A1.1081 (16)0.3359 (6)1.0380 (8)0.035 (3)*0.30
O2'0.7594 (3)0.30617 (10)1.03511 (16)0.0396 (5)
O3'0.7583 (3)0.33099 (10)0.81953 (15)0.0345 (5)
O4'0.4586 (3)0.42734 (11)0.96017 (18)0.0522 (7)
O10'1.1010 (4)0.43427 (13)1.0009 (3)0.0363 (7)0.70
H10'1.24220.43201.00100.044*0.70
O10A1.0293 (10)0.4441 (4)1.0690 (7)0.0454 (19)*0.30
O20'0.8904 (3)0.32229 (11)1.21112 (17)0.0467 (6)
O30'0.9941 (3)0.38557 (13)0.7613 (2)0.0546 (6)
N4'0.4144 (3)0.37091 (13)0.7977 (2)0.0407 (7)
H41'0.29200.37470.79180.049*
H42'0.46620.35050.74360.049*
O1W1.3569 (10)0.4791 (4)1.1373 (6)0.049 (2)*0.30
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0278 (17)0.0284 (17)0.0353 (18)0.0013 (14)0.0077 (15)0.0064 (15)
C20.0246 (16)0.0333 (18)0.0257 (16)0.0056 (13)0.0070 (13)0.0056 (14)
C30.0265 (16)0.0296 (17)0.0257 (16)0.0086 (13)0.0050 (13)0.0068 (13)
C40.0256 (16)0.0268 (16)0.0291 (17)0.0018 (13)0.0037 (14)0.0026 (14)
C200.0264 (16)0.0308 (18)0.0334 (17)0.0029 (14)0.0009 (14)0.0047 (15)
C210.0280 (17)0.042 (2)0.0293 (16)0.0055 (14)0.0013 (14)0.0004 (15)
C220.0319 (18)0.047 (2)0.0358 (18)0.0026 (16)0.0041 (15)0.0027 (17)
C230.044 (2)0.054 (2)0.050 (2)0.0078 (17)0.0070 (19)0.0150 (19)
C240.041 (2)0.076 (3)0.034 (2)0.009 (2)0.0001 (17)0.014 (2)
C250.049 (2)0.071 (3)0.039 (2)0.002 (2)0.0102 (18)0.003 (2)
C260.043 (2)0.043 (2)0.0371 (19)0.0037 (16)0.0071 (16)0.0012 (16)
C300.0189 (15)0.0288 (17)0.0287 (17)0.0031 (13)0.0032 (12)0.0035 (14)
C310.0200 (15)0.0259 (17)0.0282 (17)0.0038 (13)0.0057 (13)0.0001 (14)
C320.0311 (17)0.0341 (18)0.0312 (17)0.0061 (14)0.0039 (14)0.0084 (15)
C330.0407 (19)0.0267 (17)0.042 (2)0.0096 (15)0.0067 (16)0.0017 (15)
C340.0369 (19)0.0343 (19)0.0362 (19)0.0064 (15)0.0015 (15)0.0060 (16)
C350.043 (2)0.0336 (18)0.0269 (17)0.0012 (15)0.0065 (14)0.0007 (15)
C360.0384 (18)0.0232 (16)0.0304 (17)0.0024 (14)0.0033 (14)0.0035 (14)
O10.0275 (12)0.0599 (16)0.0343 (13)0.0125 (11)0.0056 (10)0.0138 (11)
O20.0272 (11)0.0297 (12)0.0322 (11)0.0012 (9)0.0111 (9)0.0026 (10)
O30.0294 (11)0.0270 (11)0.0284 (10)0.0082 (9)0.0070 (9)0.0028 (9)
O40.0250 (11)0.0361 (12)0.0374 (12)0.0041 (10)0.0056 (9)0.0119 (11)
O100.0219 (12)0.0436 (13)0.0348 (12)0.0020 (10)0.0100 (10)0.0089 (10)
O200.0385 (13)0.0393 (13)0.0408 (13)0.0065 (11)0.0072 (11)0.0038 (11)
O300.0361 (12)0.0415 (13)0.0266 (12)0.0063 (10)0.0045 (9)0.0027 (10)
N40.0266 (14)0.0343 (15)0.0345 (14)0.0038 (11)0.0108 (11)0.0105 (12)
C1'0.057 (4)0.036 (4)0.014 (3)0.006 (3)0.000 (3)0.011 (3)
C2'0.063 (2)0.0244 (19)0.044 (2)0.0038 (16)0.0171 (18)0.0033 (16)
C3'0.049 (2)0.0286 (17)0.0350 (18)0.0032 (16)0.0028 (15)0.0016 (16)
C4'0.048 (2)0.0284 (19)0.0316 (17)0.0041 (16)0.0007 (16)0.0037 (15)
C20'0.043 (2)0.044 (2)0.0242 (18)0.0104 (17)0.0002 (14)0.0044 (16)
C21'0.0355 (18)0.039 (2)0.0269 (17)0.0033 (15)0.0026 (14)0.0010 (15)
C22'0.041 (2)0.057 (2)0.0304 (18)0.0009 (17)0.0034 (15)0.0048 (17)
C23'0.049 (2)0.058 (3)0.046 (2)0.0008 (19)0.0009 (19)0.014 (2)
C24'0.055 (2)0.042 (2)0.056 (2)0.0044 (18)0.016 (2)0.003 (2)
C25'0.056 (2)0.044 (2)0.042 (2)0.0082 (18)0.0127 (18)0.0113 (18)
C26'0.043 (2)0.048 (2)0.0304 (18)0.0043 (17)0.0033 (15)0.0053 (17)
C30'0.037 (2)0.043 (2)0.047 (2)0.0029 (18)0.0002 (16)0.0196 (18)
C31'0.0313 (18)0.049 (2)0.0309 (18)0.0099 (16)0.0012 (15)0.0055 (16)
C32'0.037 (2)0.078 (3)0.040 (2)0.0128 (19)0.0033 (17)0.022 (2)
C33'0.045 (2)0.111 (4)0.035 (2)0.037 (3)0.0008 (18)0.002 (3)
C34'0.042 (2)0.098 (4)0.048 (2)0.032 (2)0.0113 (19)0.027 (2)
C35'0.034 (2)0.062 (3)0.057 (2)0.0150 (17)0.0147 (18)0.015 (2)
C36'0.0306 (18)0.050 (2)0.040 (2)0.0088 (17)0.0044 (15)0.0030 (18)
O1'0.057 (3)0.030 (2)0.037 (3)0.0063 (19)0.003 (2)0.003 (2)
O2'0.0556 (14)0.0319 (12)0.0278 (12)0.0022 (10)0.0067 (10)0.0020 (10)
O3'0.0399 (12)0.0325 (12)0.0305 (11)0.0009 (10)0.0025 (10)0.0021 (10)
O4'0.0687 (17)0.0465 (16)0.0404 (14)0.0185 (13)0.0033 (12)0.0114 (12)
O10'0.0395 (19)0.0224 (17)0.046 (2)0.0030 (14)0.0031 (16)0.0046 (15)
O20'0.0607 (15)0.0470 (14)0.0289 (12)0.0059 (12)0.0070 (11)0.0160 (11)
O30'0.0489 (15)0.0425 (14)0.0721 (17)0.0021 (13)0.0065 (13)0.0194 (14)
N4'0.0345 (16)0.0506 (18)0.0370 (15)0.0063 (13)0.0043 (13)0.0042 (14)
Geometric parameters (Å, º) top
C1—O11.204 (3)C1'—O10A1.640 (10)
C1—O101.317 (3)C1A—O1A1.187 (15)
C1—C21.518 (4)C1A—O10A1.346 (13)
C2—O21.440 (3)C1A—C2'1.367 (11)
C2—C31.523 (4)C1A—O10'1.450 (12)
C2—H20.9614C1A—O1'1.558 (11)
C3—O31.438 (3)C2'—O2'1.436 (4)
C3—C41.518 (4)C2'—C3'1.524 (4)
C3—H30.9614C2'—H2'0.9612
C4—O41.253 (3)C3'—O3'1.440 (3)
C4—N41.317 (3)C3'—C4'1.527 (4)
C20—O201.213 (3)C3'—H3'0.9614
C20—O21.364 (3)C4'—O4'1.235 (3)
C20—C211.467 (4)C4'—N4'1.317 (4)
C21—C261.389 (4)C20'—O20'1.217 (3)
C21—C221.397 (5)C20'—O2'1.362 (3)
C22—C231.392 (4)C20'—C21'1.475 (4)
C22—H220.9614C21'—C22'1.393 (4)
C23—C241.384 (5)C21'—C26'1.396 (4)
C23—H230.9613C22'—C23'1.381 (5)
C24—C251.388 (5)C22'—H22'0.9613
C24—H240.9613C23'—C24'1.375 (5)
C25—C261.395 (4)C23'—H23'0.9613
C25—H250.9612C24'—C25'1.384 (5)
C26—H260.9613C24'—H24'0.9613
C30—O301.210 (3)C25'—C26'1.389 (5)
C30—O31.365 (3)C25'—H25'0.9614
C30—C311.473 (4)C26'—H26'0.9613
C31—C321.389 (4)C30'—O30'1.209 (4)
C31—C361.398 (4)C30'—O3'1.365 (4)
C32—C331.372 (4)C30'—C31'1.477 (5)
C32—H320.9613C31'—C36'1.381 (4)
C33—C341.392 (4)C31'—C32'1.403 (4)
C33—H330.9613C32'—C33'1.384 (5)
C34—C351.377 (4)C32'—H32'0.9613
C34—H340.9613C33'—C34'1.379 (6)
C35—C361.384 (4)C33'—H33'0.9613
C35—H350.9613C34'—C35'1.381 (5)
C36—H360.9613C34'—H34'0.9614
O10—H100.88 (4)C35'—C36'1.395 (5)
N4—H410.9011C35'—H35'0.9613
N4—H420.9012C36'—H36'0.9612
C1'—C1A0.573 (10)O1'—O1A0.529 (10)
C1'—O1A0.982 (12)O10'—O10A1.060 (8)
C1'—O1'1.197 (7)O10'—H10'1.0451
C1'—O10'1.329 (6)N4'—H41'0.9011
C1'—C2'1.614 (7)N4'—H42'0.9013
O1—C1—O10125.6 (3)O10A—C1A—O10'44.4 (5)
O1—C1—C2122.5 (3)C2'—C1A—O10'121.1 (8)
O10—C1—C2111.8 (3)C1'—C1A—O1'42.1 (12)
O2—C2—C1110.5 (2)O1A—C1A—O1'15.9 (6)
O2—C2—C3106.6 (2)O10A—C1A—O1'134.8 (9)
C1—C2—C3110.7 (2)C2'—C1A—O1'114.3 (8)
O2—C2—H2109.5O10'—C1A—O1'96.9 (6)
C1—C2—H2109.7C1A—C2'—O2'109.6 (5)
C3—C2—H2109.8C1A—C2'—C3'124.1 (5)
O3—C3—C4109.6 (2)O2'—C2'—C3'105.7 (3)
O3—C3—C2110.2 (2)C1A—C2'—C1'20.0 (4)
C4—C3—C2108.9 (2)O2'—C2'—C1'109.6 (3)
O3—C3—H3109.4C3'—C2'—C1'106.7 (3)
C4—C3—H3109.2C1A—C2'—H2'94.6
C2—C3—H3109.6O2'—C2'—H2'110.5
O4—C4—N4125.0 (3)C3'—C2'—H2'111.8
O4—C4—C3116.6 (2)C1'—C2'—H2'112.2
N4—C4—C3118.4 (3)O3'—C3'—C2'109.3 (2)
O20—C20—O2121.3 (3)O3'—C3'—C4'109.3 (2)
O20—C20—C21125.6 (3)C2'—C3'—C4'112.3 (3)
O2—C20—C21113.0 (3)O3'—C3'—H3'108.5
C26—C21—C22120.2 (3)C2'—C3'—H3'108.4
C26—C21—C20122.6 (3)C4'—C3'—H3'108.9
C22—C21—C20117.1 (3)O4'—C4'—N4'124.5 (3)
C23—C22—C21119.8 (3)O4'—C4'—C3'118.7 (3)
C23—C22—H22120.1N4'—C4'—C3'116.7 (3)
C21—C22—H22120.1O20'—C20'—O2'121.4 (3)
C24—C23—C22119.8 (3)O20'—C20'—C21'126.4 (3)
C24—C23—H23119.9O2'—C20'—C21'112.2 (3)
C22—C23—H23120.3C22'—C21'—C26'119.7 (3)
C23—C24—C25120.5 (3)C22'—C21'—C20'118.3 (3)
C23—C24—H24120.5C26'—C21'—C20'122.0 (3)
C25—C24—H24118.9C23'—C22'—C21'119.4 (3)
C24—C25—C26119.9 (3)C23'—C22'—H22'120.7
C24—C25—H25120.4C21'—C22'—H22'119.9
C26—C25—H25119.7C24'—C23'—C22'121.2 (3)
C21—C26—C25119.7 (3)C24'—C23'—H23'119.5
C21—C26—H26119.9C22'—C23'—H23'119.3
C25—C26—H26120.4C23'—C24'—C25'119.9 (3)
O30—C30—O3122.6 (3)C23'—C24'—H24'120.5
O30—C30—C31126.2 (3)C25'—C24'—H24'119.6
O3—C30—C31111.1 (2)C24'—C25'—C26'119.9 (3)
C32—C31—C36120.1 (3)C24'—C25'—H25'120.5
C32—C31—C30118.7 (3)C26'—C25'—H25'119.6
C36—C31—C30121.2 (3)C25'—C26'—C21'119.9 (3)
C33—C32—C31120.2 (3)C25'—C26'—H26'119.6
C33—C32—H32119.8C21'—C26'—H26'120.4
C31—C32—H32120.0O30'—C30'—O3'121.7 (3)
C32—C33—C34120.1 (3)O30'—C30'—C31'125.8 (3)
C32—C33—H33119.9O3'—C30'—C31'112.5 (3)
C34—C33—H33120.0C36'—C31'—C32'120.1 (3)
C35—C34—C33119.7 (3)C36'—C31'—C30'122.2 (3)
C35—C34—H34120.2C32'—C31'—C30'117.7 (3)
C33—C34—H34120.1C33'—C32'—C31'119.9 (4)
C34—C35—C36121.0 (3)C33'—C32'—H32'120.4
C34—C35—H35119.7C31'—C32'—H32'119.7
C36—C35—H35119.3C34'—C33'—C32'119.7 (4)
C35—C36—C31118.8 (3)C34'—C33'—H33'119.5
C35—C36—H36120.7C32'—C33'—H33'120.7
C31—C36—H36120.5C33'—C34'—C35'120.7 (4)
C20—O2—C2113.1 (2)C33'—C34'—H34'119.9
C30—O3—C3117.4 (2)C35'—C34'—H34'119.4
C1—O10—H10112 (2)C34'—C35'—C36'120.1 (4)
C4—N4—H41120.6C34'—C35'—H35'120.7
C4—N4—H42119.4C36'—C35'—H35'119.2
H41—N4—H42120.0C31'—C36'—C35'119.5 (3)
C1A—C1'—O1A96.0 (16)C31'—C36'—H36'119.6
C1A—C1'—O1'119.1 (16)C35'—C36'—H36'120.9
O1A—C1'—O1'25.7 (6)O1A—O1'—C1'53.8 (16)
C1A—C1'—O10'90.2 (15)O1A—O1'—C1A38.0 (17)
O1A—C1'—O10'120.4 (9)C1'—O1'—C1A18.7 (5)
O1'—C1'—O10'126.0 (5)O1'—O1A—C1'100.5 (19)
C1A—C1'—C2'54.9 (14)O1'—O1A—C1A126 (2)
O1A—C1'—C2'119.1 (9)C1'—O1A—C1A28.7 (6)
O1'—C1'—C2'121.4 (5)C20'—O2'—C2'116.1 (2)
O10'—C1'—C2'112.6 (4)C30'—O3'—C3'118.9 (2)
C1A—C1'—O10A50.1 (14)O10A—O10'—C1'85.9 (5)
O1A—C1'—O10A118.8 (8)O10A—O10'—C1A62.6 (5)
O1'—C1'—O10A141.7 (5)C1'—O10'—C1A23.3 (4)
O10'—C1'—O10A40.1 (3)O10A—O10'—H10'127.7
C2'—C1'—O10A84.4 (4)C1'—O10'—H10'109.8
C1'—C1A—O1A55.4 (13)C1A—O10'—H10'122.0
C1'—C1A—O10A110.8 (18)O10'—O10A—C1A73.0 (7)
O1A—C1A—O10A128.3 (11)O10'—O10A—C1'54.0 (4)
C1'—C1A—C2'105.1 (16)C1A—O10A—C1'19.1 (5)
O1A—C1A—C2'124.3 (11)C4'—N4'—H41'119.8
O10A—C1A—C2'107.2 (8)C4'—N4'—H42'120.2
C1'—C1A—O10'66.5 (14)H41'—N4'—H42'120.0
O1A—C1A—O10'99.0 (9)
O1—C1—C2—O228.5 (4)C21'—C22'—C23'—C24'0.1 (5)
O10—C1—C2—O2154.9 (2)C22'—C23'—C24'—C25'0.9 (5)
O1—C1—C2—C389.5 (3)C23'—C24'—C25'—C26'1.5 (5)
O10—C1—C2—C387.2 (3)C24'—C25'—C26'—C21'1.1 (5)
O2—C2—C3—O371.0 (2)C22'—C21'—C26'—C25'0.0 (5)
C1—C2—C3—O349.3 (3)C20'—C21'—C26'—C25'178.4 (3)
O2—C2—C3—C449.2 (3)O30'—C30'—C31'—C36'166.6 (3)
C1—C2—C3—C4169.5 (2)O3'—C30'—C31'—C36'14.5 (4)
O3—C3—C4—O4173.7 (2)O30'—C30'—C31'—C32'14.4 (5)
C2—C3—C4—O465.7 (3)O3'—C30'—C31'—C32'164.6 (3)
O3—C3—C4—N47.4 (3)C36'—C31'—C32'—C33'0.5 (5)
C2—C3—C4—N4113.1 (3)C30'—C31'—C32'—C33'178.5 (3)
O20—C20—C21—C26177.7 (3)C31'—C32'—C33'—C34'0.8 (5)
O2—C20—C21—C265.6 (4)C32'—C33'—C34'—C35'0.1 (5)
O20—C20—C21—C225.4 (4)C33'—C34'—C35'—C36'0.9 (5)
O2—C20—C21—C22171.2 (3)C32'—C31'—C36'—C35'0.4 (5)
C26—C21—C22—C232.3 (4)C30'—C31'—C36'—C35'179.5 (3)
C20—C21—C22—C23174.7 (3)C34'—C35'—C36'—C31'1.2 (5)
C21—C22—C23—C241.1 (5)C1A—C1'—O1'—O1A28 (3)
C22—C23—C24—C250.5 (5)O10'—C1'—O1'—O1A86 (2)
C23—C24—C25—C260.9 (5)C2'—C1'—O1'—O1A93 (2)
C22—C21—C26—C251.9 (5)O10A—C1'—O1'—O1A33 (2)
C20—C21—C26—C25174.8 (3)O1A—C1'—O1'—C1A28 (3)
C24—C25—C26—C210.3 (5)O10'—C1'—O1'—C1A114 (2)
O30—C30—C31—C3238.1 (4)C2'—C1'—O1'—C1A64.5 (18)
O3—C30—C31—C32141.9 (2)O10A—C1'—O1'—C1A61.4 (17)
O30—C30—C31—C36142.2 (3)C1'—C1A—O1'—O1A142 (3)
O3—C30—C31—C3637.8 (3)O10A—C1A—O1'—O1A73 (3)
C36—C31—C32—C331.2 (4)C2'—C1A—O1'—O1A132 (3)
C30—C31—C32—C33178.5 (3)O10'—C1A—O1'—O1A99 (3)
C31—C32—C33—C342.1 (4)O1A—C1A—O1'—C1'142 (3)
C32—C33—C34—C350.4 (4)O10A—C1A—O1'—C1'69.4 (18)
C33—C34—C35—C362.3 (5)C2'—C1A—O1'—C1'85.8 (18)
C34—C35—C36—C313.1 (5)O10'—C1A—O1'—C1'43.0 (15)
C32—C31—C36—C351.4 (4)C1A—O1'—O1A—C1'14.2 (13)
C30—C31—C36—C35178.9 (3)C1'—O1'—O1A—C1A14.2 (13)
O20—C20—O2—C23.7 (4)C1A—C1'—O1A—O1'156 (2)
C21—C20—O2—C2173.1 (2)O10'—C1'—O1A—O1'110.6 (17)
C1—C2—O2—C2066.4 (3)C2'—C1'—O1A—O1'102.7 (18)
C3—C2—O2—C20173.1 (2)O10A—C1'—O1A—O1'157.1 (15)
O30—C30—O3—C31.8 (4)O1'—C1'—O1A—C1A156 (2)
C31—C30—O3—C3178.2 (2)O10'—C1'—O1A—C1A93.8 (16)
C4—C3—O3—C30133.0 (2)C2'—C1'—O1A—C1A52.9 (15)
C2—C3—O3—C30107.3 (2)O10A—C1'—O1A—C1A47.3 (14)
O1'—C1'—C1A—O1A11.9 (10)C1'—C1A—O1A—O1'30 (3)
O10'—C1'—C1A—O1A120.6 (10)O10A—C1A—O1A—O1'120 (2)
C2'—C1'—C1A—O1A121.6 (11)C2'—C1A—O1A—O1'55 (3)
O10A—C1'—C1A—O1A122.9 (12)O10'—C1A—O1A—O1'83 (3)
O1A—C1'—C1A—O10A122.9 (12)O10A—C1A—O1A—C1'90.3 (19)
O1'—C1'—C1A—O10A134.8 (10)C2'—C1A—O1A—C1'84.9 (18)
O10'—C1'—C1A—O10A2.3 (12)O10'—C1A—O1A—C1'53.1 (13)
C2'—C1'—C1A—O10A115.5 (17)O1'—C1A—O1A—C1'30 (3)
O1A—C1'—C1A—C2'121.6 (11)O20'—C20'—O2'—C2'13.3 (4)
O1'—C1'—C1A—C2'109.7 (11)C21'—C20'—O2'—C2'165.7 (2)
O10'—C1'—C1A—C2'117.8 (9)C1A—C2'—O2'—C20'46.5 (6)
O10A—C1'—C1A—C2'115.5 (17)C3'—C2'—O2'—C20'177.5 (2)
O1A—C1'—C1A—O10'120.6 (10)C1'—C2'—O2'—C20'67.8 (3)
O1'—C1'—C1A—O10'132.5 (12)O30'—C30'—O3'—C3'5.1 (4)
C2'—C1'—C1A—O10'117.8 (9)C31'—C30'—O3'—C3'175.8 (2)
O10A—C1'—C1A—O10'2.3 (12)C2'—C3'—O3'—C30'93.8 (3)
O1A—C1'—C1A—O1'11.9 (10)C4'—C3'—O3'—C30'143.0 (3)
O10'—C1'—C1A—O1'132.5 (12)C1A—C1'—O10'—O10A2.8 (15)
C2'—C1'—C1A—O1'109.7 (11)O1A—C1'—O10'—O10A99.8 (10)
O10A—C1'—C1A—O1'134.8 (10)O1'—C1'—O10'—O10A130.0 (7)
C1'—C1A—C2'—O2'93.6 (17)C2'—C1'—O10'—O10A48.8 (6)
O1A—C1A—C2'—O2'35.5 (13)O1A—C1'—O10'—C1A97.1 (16)
O10A—C1A—C2'—O2'148.5 (6)O1'—C1'—O10'—C1A127.2 (17)
O10'—C1A—C2'—O2'165.0 (7)C2'—C1'—O10'—C1A51.6 (14)
O1'—C1A—C2'—O2'49.7 (8)O10A—C1'—O10'—C1A2.8 (15)
C1'—C1A—C2'—C3'32 (2)C1'—C1A—O10'—O10A176.9 (17)
O1A—C1A—C2'—C3'90.5 (12)O1A—C1A—O10'—O10A137.3 (10)
O10A—C1A—C2'—C3'85.5 (8)C2'—C1A—O10'—O10A82.9 (10)
O10'—C1A—C2'—C3'38.9 (11)O1'—C1A—O10'—O10A153.2 (8)
O1'—C1A—C2'—C3'76.3 (9)O1A—C1A—O10'—C1'45.8 (12)
O1A—C1A—C2'—C1'58.1 (16)O10A—C1A—O10'—C1'176.9 (17)
O10A—C1A—C2'—C1'118 (2)C2'—C1A—O10'—C1'94.0 (17)
O10'—C1A—C2'—C1'71.4 (16)O1'—C1A—O10'—C1'29.9 (10)
O1'—C1A—C2'—C1'43.9 (13)C1'—O10'—O10A—C1A1.2 (7)
O1A—C1'—C2'—C1A75.8 (19)C1A—O10'—O10A—C1'1.2 (7)
O1'—C1'—C2'—C1A105.5 (19)C1'—C1A—O10A—O10'3.0 (16)
O10'—C1'—C2'—C1A73.3 (17)O1A—C1A—O10A—O10'58.6 (12)
O10A—C1'—C2'—C1A44.1 (17)C2'—C1A—O10A—O10'117.2 (8)
C1A—C1'—C2'—O2'93.6 (18)O1'—C1A—O10A—O10'39.2 (11)
O1A—C1'—C2'—O2'17.8 (9)O1A—C1A—O10A—C1'61.7 (16)
O1'—C1'—C2'—O2'11.9 (6)C2'—C1A—O10A—C1'114 (2)
O10'—C1'—C2'—O2'166.9 (3)O10'—C1A—O10A—C1'3.0 (16)
O10A—C1'—C2'—O2'137.7 (4)O1'—C1A—O10A—C1'42.2 (12)
C1A—C1'—C2'—C3'152.4 (17)C1A—C1'—O10A—O10'176.4 (19)
O1A—C1'—C2'—C3'131.9 (8)O1A—C1'—O10A—O10'104.1 (11)
O1'—C1'—C2'—C3'102.1 (5)O1'—C1'—O10A—O10'88.3 (10)
O10'—C1'—C2'—C3'79.0 (4)C2'—C1'—O10A—O10'135.7 (5)
O10A—C1'—C2'—C3'108.2 (4)O1A—C1'—O10A—C1A72.3 (18)
C1A—C2'—C3'—O3'76.5 (7)O1'—C1'—O10A—C1A88.1 (19)
O2'—C2'—C3'—O3'51.3 (3)O10'—C1'—O10A—C1A176.4 (19)
C1'—C2'—C3'—O3'65.4 (3)C2'—C1'—O10A—C1A47.9 (17)
C1A—C2'—C3'—C4'162.1 (6)H2—C2—O2—C2054.5
O2'—C2'—C3'—C4'70.2 (3)H3—C3—O3—C3013.3
C1'—C2'—C3'—C4'173.2 (3)H2'—C2'—O2'—C20'56.4
O3'—C3'—C4'—O4'161.6 (2)H3'—C3'—O3'—C30'24.3
C2'—C3'—C4'—O4'40.1 (4)H2—C2—C4—O46.5
O3'—C3'—C4'—N4'21.7 (4)H2—C2—C20—O2053.3
C2'—C3'—C4'—N4'143.2 (3)H3—C3—C1—O1011.2
O20'—C20'—C21'—C22'4.8 (5)H3—C3—C30—O3011.2
O2'—C20'—C21'—C22'174.1 (3)H2'—C2'—C4'—O4'11.0
O20'—C20'—C21'—C26'176.8 (3)H2'—C2'—C20'—O20'40.0
O2'—C20'—C21'—C26'4.3 (4)H3'—C3'—C1'—O10'18.6
C26'—C21'—C22'—C23'0.6 (5)H3'—C3'—C30'—O30'18.9
C20'—C21'—C22'—C23'177.9 (3)
(boh2) (R,R)-(-)-O,O'-Dibenzoyltartaric acid mono(N-methylamide) top
Crystal data top
(C19H17NO7)·(H2O)Dx = 1.355 Mg m3
Mr = 389.35Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121Cell parameters from 40 reflections
a = 8.7977 (8) Åθ = 12.8–23.9°
b = 10.752 (1) ŵ = 0.91 mm1
c = 20.177 (2) ÅT = 293 K
V = 1908.6 (3) Å3Prism, colourless
Z = 40.3 × 0.2 × 0.1 mm
F(000) = 816
Data collection top
KM-4 four circle
diffractometer
Rint = 0.013
Radiation source: fine-focus sealed tubeθmax = 67.9°, θmin = 4.4°
Graphite monochromatorh = 99
Θ–2Θ scansk = 012
3086 measured reflectionsl = 024
2841 independent reflections2 standard reflections every 100 reflections
2522 reflections with I > 2σ(I) intensity decay: 2.8%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.028Calculated w = 1/[σ2(Fo2) + (0.0425P)2 + 0.1715P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.076(Δ/σ)max < 0.001
S = 1.08Δρmax = 0.12 e Å3
2841 reflectionsΔρmin = 0.13 e Å3
266 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0052 (3)
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: 0.13 (19)
Crystal data top
(C19H17NO7)·(H2O)V = 1908.6 (3) Å3
Mr = 389.35Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 8.7977 (8) ŵ = 0.91 mm1
b = 10.752 (1) ÅT = 293 K
c = 20.177 (2) Å0.3 × 0.2 × 0.1 mm
Data collection top
KM-4 four circle
diffractometer
Rint = 0.013
3086 measured reflections2 standard reflections every 100 reflections
2841 independent reflections intensity decay: 2.8%
2522 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.028H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.076Δρmax = 0.12 e Å3
S = 1.08Δρmin = 0.13 e Å3
2841 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
266 parametersAbsolute structure parameter: 0.13 (19)
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
C10.2694 (2)0.45907 (18)0.76410 (9)0.0447 (4)
C20.0993 (2)0.47894 (16)0.76102 (9)0.0420 (4)
H20.05060.40010.75420.040*
C30.0414 (2)0.53418 (16)0.82515 (8)0.0415 (4)
H30.07370.48080.86060.040*
C40.1314 (2)0.54050 (17)0.82723 (8)0.0433 (4)
C200.0747 (2)0.51075 (17)0.64673 (9)0.0448 (4)
C210.0155 (2)0.58988 (17)0.59351 (10)0.0450 (4)
C220.0347 (3)0.5498 (2)0.52880 (10)0.0635 (6)
H220.08980.47460.51980.070*
C230.0293 (4)0.6162 (2)0.47761 (11)0.0739 (7)
H230.01330.58990.43270.080*
C240.1134 (3)0.7205 (2)0.49004 (11)0.0652 (6)
H240.16010.76470.45410.080*
C250.1299 (3)0.7625 (2)0.55403 (11)0.0661 (6)
H250.18670.83690.56260.080*
C260.0656 (3)0.69728 (18)0.60571 (10)0.0574 (5)
H260.07840.72610.65040.070*
C300.1956 (2)0.66716 (19)0.89077 (9)0.0500 (5)
C310.2653 (2)0.79004 (18)0.89572 (10)0.0480 (5)
C320.3324 (3)0.8245 (2)0.95496 (12)0.0769 (7)
H320.33210.76860.99210.070*
C330.4004 (4)0.9404 (3)0.95987 (17)0.0975 (10)
H330.44240.96681.00150.110*
C340.4044 (3)1.0181 (3)0.90694 (18)0.0922 (9)
H340.45651.09620.91070.110*
C350.3402 (3)0.9847 (2)0.84839 (14)0.0747 (7)
H350.34261.04110.81150.110*
C360.2694 (2)0.87053 (19)0.84221 (11)0.0531 (5)
H360.22350.84640.80100.070*
C410.3574 (3)0.6626 (2)0.85022 (13)0.0707 (6)
H4110.40720.60780.81960.140*
H4120.38570.74720.84130.140*
H4130.38690.64280.89480.140*
N40.19436 (18)0.64710 (15)0.84234 (8)0.0506 (4)
H40.13370.71350.84860.070*
O10.36154 (16)0.53294 (13)0.74493 (8)0.0650 (4)
O20.05716 (15)0.56050 (10)0.70785 (6)0.0451 (3)
O30.10880 (14)0.65382 (10)0.83588 (6)0.0427 (3)
O40.20046 (17)0.44394 (13)0.81663 (8)0.0647 (4)
O100.30009 (18)0.35320 (13)0.79278 (7)0.0567 (4)
H100.411 (3)0.341 (2)0.7946 (12)0.076 (7)*
O200.1307 (2)0.40943 (13)0.63916 (7)0.0606 (4)
O300.2121 (3)0.58422 (17)0.92939 (10)0.1019 (8)
O1W0.57215 (18)0.27430 (15)0.81209 (8)0.0558 (4)
H1W0.649 (3)0.328 (3)0.8139 (12)0.077 (8)*
H2W0.605 (4)0.206 (3)0.7906 (15)0.105 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0488 (11)0.0359 (10)0.0495 (9)0.0006 (9)0.0035 (8)0.0014 (9)
C20.0454 (10)0.0320 (9)0.0485 (9)0.0013 (8)0.0040 (8)0.0037 (8)
C30.0456 (10)0.0344 (9)0.0445 (9)0.0052 (8)0.0048 (8)0.0048 (8)
C40.0454 (10)0.0403 (10)0.0441 (9)0.0065 (9)0.0008 (8)0.0012 (8)
C200.0483 (10)0.0373 (10)0.0488 (10)0.0019 (9)0.0077 (8)0.0020 (8)
C210.0537 (11)0.0385 (9)0.0428 (9)0.0014 (8)0.0056 (8)0.0005 (8)
C220.0854 (16)0.0560 (12)0.0491 (11)0.0101 (12)0.0136 (11)0.0027 (10)
C230.109 (2)0.0724 (16)0.0401 (10)0.0027 (15)0.0038 (12)0.0010 (10)
C240.0875 (17)0.0551 (13)0.0530 (12)0.0041 (13)0.0093 (11)0.0114 (10)
C250.0911 (17)0.0453 (12)0.0617 (13)0.0117 (12)0.0117 (12)0.0027 (10)
C260.0786 (14)0.0468 (11)0.0470 (10)0.0105 (11)0.0030 (10)0.0043 (9)
C300.0545 (11)0.0498 (11)0.0456 (10)0.0001 (10)0.0111 (9)0.0001 (10)
C310.0405 (10)0.0483 (11)0.0553 (11)0.0002 (8)0.0053 (8)0.0095 (9)
C320.0945 (19)0.0668 (15)0.0694 (14)0.0060 (15)0.0277 (13)0.0105 (12)
C330.108 (3)0.0798 (19)0.104 (2)0.0200 (18)0.0438 (19)0.0300 (18)
C340.0836 (19)0.0637 (16)0.129 (2)0.0244 (15)0.0124 (18)0.0186 (17)
C350.0723 (16)0.0578 (14)0.0939 (18)0.0213 (12)0.0072 (14)0.0025 (13)
C360.0490 (12)0.0494 (11)0.0610 (12)0.0060 (9)0.0058 (9)0.0048 (10)
C410.0478 (12)0.0688 (15)0.0955 (16)0.0017 (11)0.0092 (12)0.0011 (13)
N40.0411 (8)0.0424 (9)0.0682 (10)0.0025 (7)0.0033 (8)0.0025 (8)
O10.0504 (8)0.0506 (8)0.0941 (11)0.0062 (7)0.0044 (8)0.0171 (8)
O20.0561 (8)0.0371 (7)0.0420 (6)0.0054 (6)0.0017 (6)0.0001 (5)
O30.0454 (7)0.0360 (7)0.0468 (6)0.0060 (5)0.0079 (5)0.0018 (5)
O40.0562 (9)0.0484 (8)0.0894 (11)0.0158 (7)0.0044 (8)0.0117 (8)
O100.0485 (9)0.0456 (8)0.0760 (9)0.0064 (7)0.0036 (7)0.0169 (7)
O200.0786 (10)0.0441 (8)0.0590 (8)0.0146 (7)0.0083 (7)0.0016 (6)
O300.157 (2)0.0641 (11)0.0847 (12)0.0277 (12)0.0672 (13)0.0241 (10)
O1W0.0462 (8)0.0468 (8)0.0744 (10)0.0027 (7)0.0012 (7)0.0050 (7)
Geometric parameters (Å, º) top
C1—O11.199 (2)C26—H260.9601
C1—O101.305 (2)C30—O301.193 (2)
C1—C21.513 (3)C30—O31.353 (2)
C2—O21.434 (2)C30—C311.460 (3)
C2—C31.512 (2)C31—C321.384 (3)
C2—H20.9599C31—C361.384 (3)
C3—O31.433 (2)C32—C331.386 (4)
C3—C41.522 (3)C32—H320.9600
C3—H30.9600C33—C341.356 (4)
C4—O41.222 (2)C33—H330.9599
C4—N41.309 (2)C34—C351.358 (4)
C20—O201.205 (2)C34—H340.9600
C20—O21.353 (2)C35—C361.382 (3)
C20—C211.465 (3)C35—H350.9599
C21—C261.380 (3)C36—H360.9600
C21—C221.385 (3)C41—N41.453 (3)
C22—C231.376 (3)C41—H4110.9599
C22—H220.9599C41—H4120.9599
C23—C241.366 (3)C41—H4130.9599
C23—H230.9600N4—H40.9000
C24—C251.375 (3)O10—H100.99 (3)
C24—H240.9600O1W—H1W0.89 (3)
C25—C261.378 (3)O1W—H2W0.90 (3)
C25—H250.9600
O1—C1—O10125.53 (18)C25—C26—H26119.9
O1—C1—C2124.18 (17)C21—C26—H26119.9
O10—C1—C2110.23 (16)O30—C30—O3121.61 (18)
O2—C2—C3108.23 (14)O30—C30—C31125.49 (18)
O2—C2—C1111.88 (15)O3—C30—C31112.89 (16)
C3—C2—C1110.70 (15)C32—C31—C36119.7 (2)
O2—C2—H2108.5C32—C31—C30118.7 (2)
C3—C2—H2108.6C36—C31—C30121.56 (18)
C1—C2—H2108.8C31—C32—C33119.1 (2)
O3—C3—C2110.03 (14)C31—C32—H32120.4
O3—C3—C4111.65 (15)C33—C32—H32120.5
C2—C3—C4112.18 (14)C34—C33—C32120.6 (2)
O3—C3—H3107.6C34—C33—H33119.7
C2—C3—H3107.6C32—C33—H33119.6
C4—C3—H3107.5C33—C34—C35120.8 (2)
O4—C4—N4125.03 (17)C33—C34—H34119.3
O4—C4—C3117.00 (17)C35—C34—H34119.9
N4—C4—C3117.92 (16)C34—C35—C36120.0 (3)
O20—C20—O2121.28 (17)C34—C35—H35119.9
O20—C20—C21125.24 (17)C36—C35—H35120.1
O2—C20—C21113.45 (15)C35—C36—C31119.8 (2)
C26—C21—C22119.4 (2)C35—C36—H36120.5
C26—C21—C20122.61 (18)C31—C36—H36119.7
C22—C21—C20117.82 (18)N4—C41—H411108.1
C23—C22—C21119.7 (2)N4—C41—H412110.2
C23—C22—H22120.1H411—C41—H412110.1
C21—C22—H22120.2N4—C41—H413110.1
C24—C23—C22120.6 (2)H411—C41—H413110.1
C24—C23—H23119.7H412—C41—H413108.4
C22—C23—H23119.7C4—N4—C41122.97 (18)
C23—C24—C25119.9 (2)C4—N4—H4118.4
C23—C24—H24119.9C41—N4—H4118.6
C25—C24—H24120.2C20—O2—C2114.24 (13)
C24—C25—C26120.0 (2)C30—O3—C3116.90 (14)
C24—C25—H25119.9C1—O10—H10109.6 (14)
C26—C25—H25120.1H1W—O1W—H2W108 (3)
C25—C26—C21120.19 (19)
O1—C1—C2—O227.5 (3)C20—C21—C26—C25174.4 (2)
O10—C1—C2—O2155.04 (14)O30—C30—C31—C3213.2 (4)
O1—C1—C2—C393.3 (2)O3—C30—C31—C32167.8 (2)
O10—C1—C2—C384.15 (18)O30—C30—C31—C36164.9 (2)
O2—C2—C3—O360.75 (17)O3—C30—C31—C3614.2 (3)
C1—C2—C3—O362.21 (18)C36—C31—C32—C331.2 (4)
O2—C2—C3—C464.20 (18)C30—C31—C32—C33179.3 (2)
C1—C2—C3—C4172.85 (15)C31—C32—C33—C341.6 (5)
O3—C3—C4—O4177.84 (15)C32—C33—C34—C350.9 (5)
C2—C3—C4—O453.8 (2)C33—C34—C35—C360.1 (5)
O3—C3—C4—N44.4 (2)C34—C35—C36—C310.5 (4)
C2—C3—C4—N4128.47 (17)C32—C31—C36—C350.1 (3)
O20—C20—C21—C26171.0 (2)C30—C31—C36—C35178.2 (2)
O2—C20—C21—C267.2 (3)O4—C4—N4—C411.8 (3)
O20—C20—C21—C224.8 (3)C3—C4—N4—C41175.78 (18)
O2—C20—C21—C22176.97 (19)O20—C20—O2—C24.6 (3)
C26—C21—C22—C231.0 (4)C21—C20—O2—C2173.64 (16)
C20—C21—C22—C23175.0 (2)C3—C2—O2—C20167.38 (14)
C21—C22—C23—C241.0 (4)C1—C2—O2—C2070.39 (19)
C22—C23—C24—C252.5 (4)O30—C30—O3—C31.9 (3)
C23—C24—C25—C262.1 (4)C31—C30—O3—C3177.14 (15)
C24—C25—C26—C210.1 (4)C2—C3—O3—C30118.29 (17)
C22—C21—C26—C251.4 (3)C4—C3—O3—C30116.47 (17)
(boh3) (R,R)-(-)-O,O'-Dibenzoyltartaric acid mono(N,N-dimethylamide) top
Crystal data top
C20H19NO7F(000) = 808
Mr = 385.36Dx = 1.318 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 8.6699 (6) ŵ = 0.10 mm1
b = 12.0105 (7) ÅT = 120 K
c = 18.657 (1) ÅPrism, colourless
V = 1942.8 (2) Å30.5 × 0.2 × 0.1 mm
Z = 4
Data collection top
Kuma KM4CCD κ-geometry
diffractometer
2444 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.073
Graphite monochromatorθmax = 28.3°, θmin = 4.1°
ω scansh = 1111
19283 measured reflectionsk = 816
2726 independent reflectionsl = 2424
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 atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.117Calculated w = 1/[σ2(Fo2) + (0.0639P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max < 0.001
2726 reflectionsΔρmax = 0.22 e Å3
257 parametersΔρmin = 0.20 e Å3
0 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods
Crystal data top
C20H19NO7V = 1942.8 (2) Å3
Mr = 385.36Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.6699 (6) ŵ = 0.10 mm1
b = 12.0105 (7) ÅT = 120 K
c = 18.657 (1) Å0.5 × 0.2 × 0.1 mm
Data collection top
Kuma KM4CCD κ-geometry
diffractometer
2444 reflections with I > 2σ(I)
19283 measured reflectionsRint = 0.073
2726 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.13Δρmax = 0.22 e Å3
2726 reflectionsΔρmin = 0.20 e Å3
257 parametersAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
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
C10.0724 (3)0.1814 (2)0.29720 (12)0.0288 (5)
C20.0568 (3)0.10213 (19)0.32011 (12)0.0274 (5)
H20.12590.14110.35150.033*
C30.1483 (3)0.0578 (2)0.25687 (13)0.0275 (5)
H30.19110.11890.23030.033*
C40.2787 (3)0.0195 (2)0.28122 (13)0.0294 (5)
O10.1964 (2)0.18285 (17)0.32598 (11)0.0436 (5)
O100.0271 (2)0.24888 (14)0.24550 (10)0.0332 (4)
H100.102 (4)0.294 (3)0.2354 (18)0.056 (10)*
O20.0105 (2)0.01127 (13)0.35842 (8)0.0325 (4)
O30.04257 (18)0.00241 (13)0.21205 (8)0.0274 (4)
O40.2550 (2)0.11963 (14)0.29196 (10)0.0377 (4)
N40.4159 (2)0.02778 (17)0.29345 (11)0.0322 (5)
C410.5433 (3)0.0442 (2)0.31734 (18)0.0439 (7)
H4110.51350.07810.36180.053*
H4120.56400.10040.28210.053*
H4130.63510.00060.32390.053*
C420.4510 (3)0.1429 (2)0.27353 (16)0.0394 (6)
H4210.38080.19370.29620.047*
H4220.55470.16060.28750.047*
H4230.44360.15070.22240.047*
C200.0160 (3)0.00687 (19)0.42985 (12)0.0280 (5)
O200.0952 (3)0.07459 (19)0.45973 (11)0.0613 (7)
C210.0616 (3)0.08829 (19)0.46425 (12)0.0269 (5)
C220.0595 (3)0.0944 (2)0.53897 (14)0.0366 (6)
H220.00820.03760.56620.044*
C230.1307 (3)0.1832 (2)0.57343 (15)0.0429 (7)
H230.13080.18670.62480.052*
C240.2010 (3)0.2654 (3)0.53423 (17)0.0459 (7)
H240.24960.32640.55860.055*
C250.2028 (3)0.2605 (2)0.45977 (16)0.0447 (7)
H250.25190.31870.43290.054*
C260.1337 (3)0.1715 (2)0.42473 (14)0.0343 (6)
H260.13560.16740.37330.041*
C300.1011 (3)0.0260 (2)0.14575 (13)0.0302 (5)
O300.2332 (2)0.00535 (16)0.13089 (9)0.0391 (4)
C310.0143 (3)0.0775 (2)0.09803 (13)0.0308 (5)
C320.0281 (4)0.0958 (2)0.02714 (14)0.0389 (6)
H320.12990.07670.01110.047*
C330.0788 (4)0.1420 (2)0.01993 (15)0.0480 (8)
H330.05050.15490.06900.058*
C340.2242 (4)0.1695 (2)0.00305 (16)0.0455 (7)
H340.29700.20140.02990.055*
C350.2652 (4)0.1516 (2)0.07331 (16)0.0439 (7)
H350.36730.17070.08910.053*
C360.1618 (3)0.1045 (2)0.12116 (14)0.0344 (6)
H360.19050.09230.17020.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0308 (12)0.0302 (12)0.0255 (11)0.0054 (10)0.0003 (10)0.0060 (10)
C20.0307 (12)0.0271 (12)0.0246 (11)0.0093 (10)0.0008 (10)0.0000 (9)
C30.0274 (12)0.0248 (12)0.0303 (12)0.0052 (9)0.0029 (10)0.0020 (9)
C40.0289 (12)0.0300 (12)0.0294 (12)0.0024 (10)0.0014 (10)0.0009 (10)
O10.0305 (10)0.0562 (12)0.0440 (11)0.0029 (9)0.0059 (8)0.0019 (9)
O100.0327 (10)0.0290 (9)0.0379 (10)0.0032 (8)0.0035 (8)0.0041 (8)
O20.0423 (10)0.0301 (8)0.0251 (8)0.0141 (8)0.0012 (7)0.0018 (7)
O30.0287 (8)0.0290 (8)0.0246 (8)0.0032 (7)0.0012 (7)0.0003 (7)
O40.0366 (10)0.0275 (9)0.0490 (11)0.0050 (8)0.0106 (9)0.0067 (8)
N40.0280 (10)0.0303 (11)0.0384 (11)0.0002 (9)0.0019 (9)0.0021 (9)
C410.0351 (14)0.0371 (15)0.0596 (18)0.0041 (12)0.0121 (14)0.0011 (13)
C420.0292 (13)0.0351 (14)0.0538 (17)0.0077 (11)0.0002 (12)0.0047 (12)
C200.0286 (11)0.0273 (11)0.0280 (11)0.0013 (10)0.0054 (10)0.0021 (9)
O200.0839 (17)0.0613 (13)0.0387 (11)0.0445 (13)0.0224 (11)0.0144 (10)
C210.0243 (11)0.0280 (11)0.0285 (12)0.0011 (9)0.0012 (10)0.0035 (9)
C220.0394 (14)0.0376 (14)0.0328 (13)0.0065 (12)0.0068 (12)0.0033 (11)
C230.0439 (15)0.0505 (17)0.0343 (14)0.0093 (13)0.0052 (12)0.0117 (12)
C240.0428 (15)0.0442 (16)0.0506 (17)0.0135 (13)0.0040 (14)0.0175 (14)
C250.0498 (17)0.0365 (15)0.0480 (17)0.0157 (13)0.0001 (14)0.0006 (13)
C260.0365 (13)0.0312 (13)0.0352 (13)0.0061 (11)0.0027 (11)0.0005 (10)
C300.0333 (13)0.0262 (11)0.0310 (12)0.0023 (10)0.0026 (11)0.0032 (10)
O300.0338 (9)0.0470 (10)0.0365 (10)0.0014 (8)0.0052 (8)0.0001 (8)
C310.0384 (13)0.0247 (11)0.0293 (12)0.0070 (10)0.0033 (11)0.0018 (9)
C320.0499 (16)0.0357 (13)0.0311 (12)0.0058 (13)0.0010 (12)0.0014 (11)
C330.069 (2)0.0436 (16)0.0315 (14)0.0099 (15)0.0079 (14)0.0068 (12)
C340.062 (2)0.0333 (14)0.0414 (15)0.0038 (14)0.0211 (15)0.0016 (12)
C350.0491 (16)0.0392 (14)0.0433 (16)0.0034 (13)0.0113 (14)0.0008 (12)
C360.0413 (14)0.0325 (13)0.0293 (12)0.0025 (11)0.0041 (11)0.0010 (11)
Geometric parameters (Å, º) top
C1—O11.201 (3)C21—C261.390 (3)
C1—O101.320 (3)C21—C221.396 (3)
C1—C21.531 (3)C22—C231.390 (4)
C2—O21.429 (3)C22—H220.9599
C2—C31.518 (3)C23—C241.372 (4)
C2—H20.9600C23—H230.9601
C3—O31.436 (3)C24—C251.390 (4)
C3—C41.531 (3)C24—H240.9600
C3—H30.9600C25—C261.389 (4)
C4—O41.237 (3)C25—H250.9600
C4—N41.337 (3)C26—H260.9600
O10—H100.87 (4)C30—O301.205 (3)
O2—C201.353 (3)C30—C311.475 (4)
O3—C301.366 (3)C31—C361.388 (4)
N4—C421.464 (3)C31—C321.390 (3)
N4—C411.472 (3)C32—C331.392 (4)
C41—H4110.9599C32—H320.9600
C41—H4120.9599C33—C341.372 (5)
C41—H4130.9600C33—H330.9601
C42—H4210.9600C34—C351.375 (4)
C42—H4220.9600C34—H340.9600
C42—H4230.9600C35—C361.386 (4)
C20—O201.201 (3)C35—H350.9600
C20—C211.474 (3)C36—H360.9600
O1—C1—O10125.7 (2)C26—C21—C22119.9 (2)
O1—C1—C2122.6 (2)C26—C21—C20122.1 (2)
O10—C1—C2111.6 (2)C22—C21—C20118.0 (2)
O2—C2—C3109.51 (19)C23—C22—C21119.8 (2)
O2—C2—C1108.40 (19)C23—C22—H22120.4
C3—C2—C1112.57 (19)C21—C22—H22119.8
O2—C2—H2108.8C24—C23—C22120.2 (3)
C3—C2—H2108.6C24—C23—H23120.0
C1—C2—H2108.9C22—C23—H23119.8
O3—C3—C2107.19 (18)C23—C24—C25120.5 (3)
O3—C3—C4109.84 (18)C23—C24—H24119.5
C2—C3—C4111.59 (19)C25—C24—H24120.1
O3—C3—H3109.3C26—C25—C24119.9 (3)
C2—C3—H3109.5C26—C25—H25120.4
C4—C3—H3109.3C24—C25—H25119.7
O4—C4—N4122.2 (2)C25—C26—C21119.8 (2)
O4—C4—C3121.0 (2)C25—C26—H26120.2
N4—C4—C3116.8 (2)C21—C26—H26120.0
C1—O10—H10109 (2)O30—C30—O3121.2 (2)
C20—O2—C2116.93 (18)O30—C30—C31126.3 (2)
C30—O3—C3113.23 (18)O3—C30—C31112.4 (2)
C4—N4—C42122.8 (2)C36—C31—C32120.1 (2)
C4—N4—C41118.0 (2)C36—C31—C30122.4 (2)
C42—N4—C41118.4 (2)C32—C31—C30117.5 (2)
N4—C41—H411108.0C31—C32—C33119.2 (3)
N4—C41—H412110.2C31—C32—H32120.2
H411—C41—H412110.1C33—C32—H32120.6
N4—C41—H413109.9C34—C33—C32120.7 (3)
H411—C41—H413110.1C34—C33—H33119.6
H412—C41—H413108.4C32—C33—H33119.7
N4—C42—H421110.9C33—C34—C35119.9 (3)
N4—C42—H422109.6C33—C34—H34120.0
H421—C42—H422109.5C35—C34—H34120.1
N4—C42—H423109.3C34—C35—C36120.7 (3)
H421—C42—H423109.5C34—C35—H35119.5
H422—C42—H423108.1C36—C35—H35119.8
O20—C20—O2121.8 (2)C35—C36—C31119.4 (2)
O20—C20—C21125.7 (2)C35—C36—H36120.6
O2—C20—C21112.43 (19)C31—C36—H36119.9
O1—C1—C2—O220.7 (3)O20—C20—C21—C228.1 (4)
O10—C1—C2—O2162.20 (18)O2—C20—C21—C22172.1 (2)
O1—C1—C2—C3142.0 (2)C26—C21—C22—C230.5 (4)
O10—C1—C2—C340.9 (3)C20—C21—C22—C23179.6 (2)
O2—C2—C3—O359.9 (2)C21—C22—C23—C240.9 (4)
C1—C2—C3—O360.8 (2)C22—C23—C24—C250.4 (4)
O2—C2—C3—C460.4 (2)C23—C24—C25—C260.4 (5)
C1—C2—C3—C4178.91 (18)C24—C25—C26—C210.7 (4)
O3—C3—C4—O433.1 (3)C22—C21—C26—C250.3 (4)
C2—C3—C4—O485.6 (3)C20—C21—C26—C25178.8 (2)
O3—C3—C4—N4150.1 (2)C3—O3—C30—O306.0 (3)
C2—C3—C4—N491.2 (3)C3—O3—C30—C31174.16 (18)
C3—C2—O2—C20127.5 (2)O30—C30—C31—C36175.9 (2)
C1—C2—O2—C20109.4 (2)O3—C30—C31—C363.9 (3)
C2—C3—O3—C30166.44 (18)O30—C30—C31—C325.9 (4)
C4—C3—O3—C3072.2 (2)O3—C30—C31—C32174.3 (2)
O4—C4—N4—C42172.9 (2)C36—C31—C32—C330.4 (4)
C3—C4—N4—C4210.3 (3)C30—C31—C32—C33178.6 (2)
O4—C4—N4—C412.8 (4)C31—C32—C33—C340.1 (4)
C3—C4—N4—C41179.6 (2)C32—C33—C34—C350.2 (4)
C2—O2—C20—O201.6 (3)C33—C34—C35—C361.0 (4)
C2—O2—C20—C21178.59 (19)C34—C35—C36—C311.4 (4)
O20—C20—C21—C26171.0 (3)C32—C31—C36—C351.1 (4)
O2—C20—C21—C268.8 (3)C30—C31—C36—C35179.2 (2)
(bn13) (R,R)-(-)-O,O'-Dibenzoyltartaric acid N,N-dimethyldiamide top
Crystal data top
C20H20N2O6F(000) = 808
Mr = 384.38Dx = 1.355 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 8.9153 (6) ŵ = 0.10 mm1
b = 11.758 (1) ÅT = 150 K
c = 17.976 (1) ÅPlate, colourless
V = 1884.4 (2) Å30.40 × 0.20 × 0.05 mm
Z = 4
Data collection top
Kuma KM4CCD κ-geometry
diffractometer
1697 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.069
Graphite monochromatorθmax = 28.3°, θmin = 4.1°
ω scansh = 811
12108 measured reflectionsk = 1515
2545 independent reflectionsl = 2223
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)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.099Calculated w = 1/[σ2(Fo2) + (0.0471P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
2545 reflectionsΔρmax = 0.17 e Å3
253 parametersΔρmin = 0.23 e Å3
0 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods
Crystal data top
C20H20N2O6V = 1884.4 (2) Å3
Mr = 384.38Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.9153 (6) ŵ = 0.10 mm1
b = 11.758 (1) ÅT = 150 K
c = 17.976 (1) Å0.40 × 0.20 × 0.05 mm
Data collection top
Kuma KM4CCD κ-geometry
diffractometer
1697 reflections with I > 2σ(I)
12108 measured reflectionsRint = 0.069
2545 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 0.98Δρmax = 0.17 e Å3
2545 reflectionsΔρmin = 0.23 e Å3
253 parametersAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
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
C10.1554 (3)0.9495 (2)1.00258 (16)0.0268 (6)
C20.0044 (3)0.9472 (2)1.03195 (16)0.0265 (6)
H20.01741.01171.06400.032*
C30.1140 (3)0.9592 (2)0.96750 (16)0.0246 (6)
H30.08781.02530.93900.029*
C40.2770 (3)0.9709 (2)0.99273 (17)0.0264 (6)
C200.1138 (3)0.8643 (3)1.13987 (16)0.0288 (7)
C210.1185 (3)0.7624 (3)1.18797 (17)0.0279 (7)
C220.1850 (3)0.7741 (3)1.25814 (18)0.0384 (8)
H220.22320.84651.27380.046*
C230.1940 (4)0.6809 (4)1.3047 (2)0.0481 (9)
H230.24030.68841.35260.058*
C240.1384 (4)0.5767 (3)1.2828 (2)0.0440 (9)
H240.14840.51171.31470.053*
C250.0694 (3)0.5659 (3)1.21449 (19)0.0399 (9)
H250.02800.49421.19940.048*
C260.0590 (3)0.6583 (3)1.16705 (18)0.0319 (8)
H260.00930.65121.11990.038*
C300.1610 (3)0.8738 (3)0.85191 (16)0.0268 (7)
C310.1374 (3)0.7731 (3)0.80403 (16)0.0278 (7)
C320.2147 (3)0.7702 (3)0.73644 (17)0.0349 (8)
H320.27950.83180.72270.042*
C330.1974 (4)0.6777 (3)0.68925 (18)0.0404 (8)
H330.25170.67380.64320.048*
C340.1027 (3)0.5903 (3)0.70909 (19)0.0397 (8)
H340.09000.52670.67620.048*
C350.0238 (4)0.5931 (3)0.77557 (18)0.0385 (8)
H350.04290.53210.78840.046*
C360.0422 (3)0.6844 (3)0.82361 (17)0.0334 (8)
H360.01090.68670.87000.040*
C410.4694 (3)1.0877 (3)1.0485 (2)0.0455 (9)
H4110.53781.11691.01210.055*
H4120.46281.13921.08980.055*
H4130.50431.01571.06670.055*
C420.2303 (4)1.1767 (3)1.0076 (2)0.0503 (10)
H4210.18231.17840.95990.060*
H4220.15601.17631.04620.060*
H4230.29121.24331.01370.060*
O10.1997 (2)1.03923 (17)0.97496 (13)0.0380 (5)
O20.0317 (2)0.84678 (16)1.07580 (11)0.0268 (5)
O30.0973 (2)0.86096 (17)0.92126 (11)0.0277 (5)
O40.3591 (2)0.88621 (16)0.99564 (11)0.0329 (5)
O200.1718 (2)0.95470 (19)1.15341 (12)0.0393 (6)
O300.2256 (2)0.95943 (18)0.83470 (12)0.0351 (5)
N10.2387 (3)0.85587 (19)1.00891 (14)0.0326 (6)
H110.33340.85450.99190.039*
H120.19910.79361.03030.039*
N40.3220 (3)1.07442 (19)1.01389 (14)0.0302 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0284 (16)0.0247 (14)0.0273 (15)0.0021 (12)0.0047 (14)0.0012 (15)
C20.0313 (16)0.0219 (15)0.0264 (15)0.0011 (13)0.0011 (14)0.0026 (13)
C30.0324 (15)0.0178 (13)0.0234 (14)0.0000 (12)0.0031 (13)0.0033 (13)
C40.0274 (15)0.0233 (14)0.0285 (16)0.0023 (12)0.0059 (13)0.0028 (14)
C200.0248 (15)0.0376 (18)0.0241 (16)0.0020 (14)0.0031 (13)0.0049 (15)
C210.0233 (15)0.0343 (18)0.0260 (17)0.0026 (13)0.0016 (13)0.0014 (14)
C220.0386 (19)0.046 (2)0.0309 (18)0.0013 (17)0.0052 (15)0.0022 (17)
C230.047 (2)0.065 (3)0.0314 (19)0.005 (2)0.0083 (16)0.0066 (19)
C240.0343 (18)0.057 (2)0.041 (2)0.0047 (17)0.0008 (16)0.0189 (19)
C250.0315 (17)0.044 (2)0.045 (2)0.0012 (15)0.0015 (16)0.0088 (18)
C260.0279 (16)0.0374 (19)0.0303 (17)0.0019 (14)0.0006 (13)0.0011 (15)
C300.0254 (15)0.0294 (17)0.0256 (16)0.0067 (13)0.0036 (13)0.0019 (14)
C310.0253 (15)0.0326 (16)0.0255 (16)0.0036 (13)0.0028 (13)0.0005 (14)
C320.0363 (18)0.0395 (18)0.0289 (17)0.0027 (15)0.0043 (14)0.0007 (15)
C330.0453 (19)0.050 (2)0.0263 (18)0.0050 (18)0.0032 (15)0.0072 (16)
C340.0395 (18)0.042 (2)0.037 (2)0.0023 (16)0.0052 (16)0.0119 (17)
C350.0353 (18)0.041 (2)0.039 (2)0.0061 (16)0.0002 (16)0.0096 (16)
C360.0317 (16)0.0403 (19)0.0281 (17)0.0025 (14)0.0024 (14)0.0052 (15)
C410.0283 (17)0.0390 (19)0.069 (3)0.0073 (15)0.0002 (17)0.0133 (19)
C420.054 (2)0.0245 (15)0.073 (3)0.0021 (15)0.008 (2)0.0069 (19)
O10.0358 (12)0.0282 (11)0.0501 (14)0.0049 (10)0.0026 (11)0.0116 (11)
O20.0316 (10)0.0246 (10)0.0242 (11)0.0001 (9)0.0010 (9)0.0033 (9)
O30.0327 (11)0.0253 (11)0.0250 (11)0.0006 (9)0.0042 (9)0.0038 (10)
O40.0331 (11)0.0271 (10)0.0385 (12)0.0030 (9)0.0022 (10)0.0009 (11)
O200.0439 (13)0.0342 (12)0.0399 (13)0.0068 (11)0.0061 (11)0.0051 (11)
O300.0407 (12)0.0308 (12)0.0338 (12)0.0007 (10)0.0078 (10)0.0050 (11)
N10.0286 (13)0.0297 (13)0.0395 (16)0.0024 (11)0.0072 (12)0.0071 (13)
N40.0284 (13)0.0227 (12)0.0394 (16)0.0020 (10)0.0044 (12)0.0040 (11)
Geometric parameters (Å, º) top
C1—O11.232 (3)C30—O301.201 (3)
C1—N11.332 (3)C30—O31.378 (3)
C1—C21.519 (4)C30—C311.479 (4)
C2—O21.441 (3)C31—C361.390 (4)
C2—C31.522 (4)C31—C321.397 (4)
C2—H20.9594C32—C331.388 (4)
C3—O31.431 (3)C32—H320.9593
C3—C41.528 (4)C33—C341.377 (5)
C3—H30.9594C33—H330.9592
C4—O41.237 (3)C34—C351.387 (4)
C4—N41.337 (3)C34—H340.9595
C20—O201.207 (4)C35—C361.388 (4)
C20—O21.380 (3)C35—H350.9593
C20—C211.477 (4)C36—H360.9594
C21—C261.386 (4)C41—N41.462 (4)
C21—C221.400 (4)C41—H4110.9592
C22—C231.381 (5)C41—H4120.9595
C22—H220.9594C41—H4130.9594
C23—C241.378 (5)C42—N41.459 (4)
C23—H230.9593C42—H4210.9592
C24—C251.380 (5)C42—H4220.9592
C24—H240.9594C42—H4230.9593
C25—C261.385 (4)N1—H110.8991
C25—H250.9594N1—H120.8994
C26—H260.9594
O1—C1—N1124.3 (3)O30—C30—C31126.1 (3)
O1—C1—C2117.1 (2)O3—C30—C31112.3 (2)
N1—C1—C2118.6 (2)C36—C31—C32120.2 (3)
O2—C2—C1111.3 (2)C36—C31—C30122.7 (3)
O2—C2—C3112.6 (2)C32—C31—C30117.1 (3)
C1—C2—C3109.6 (2)C33—C32—C31119.7 (3)
O2—C2—H2107.4C33—C32—H32120.1
C1—C2—H2108.0C31—C32—H32120.2
C3—C2—H2107.8C34—C33—C32119.6 (3)
O3—C3—C2107.5 (2)C34—C33—H33119.8
O3—C3—C4110.1 (2)C32—C33—H33120.6
C2—C3—C4113.1 (2)C33—C34—C35121.1 (3)
O3—C3—H3108.5C33—C34—H34119.6
C2—C3—H3109.0C35—C34—H34119.3
C4—C3—H3108.5C34—C35—C36119.6 (3)
O4—C4—N4122.9 (3)C34—C35—H35120.3
O4—C4—C3120.2 (2)C36—C35—H35120.1
N4—C4—C3116.8 (2)C35—C36—C31119.7 (3)
O20—C20—O2121.8 (3)C35—C36—H36120.3
O20—C20—C21125.7 (3)C31—C36—H36120.0
O2—C20—C21112.5 (3)N4—C41—H411108.6
C26—C21—C22119.5 (3)N4—C41—H412110.0
C26—C21—C20123.1 (3)H411—C41—H412110.0
C22—C21—C20117.4 (3)N4—C41—H413110.0
C23—C22—C21119.5 (3)H411—C41—H413110.0
C23—C22—H22120.4H412—C41—H413108.3
C21—C22—H22120.0N4—C42—H421109.6
C24—C23—C22120.7 (3)N4—C42—H422109.1
C24—C23—H23119.5H421—C42—H422109.8
C22—C23—H23119.8N4—C42—H423110.3
C23—C24—C25119.8 (3)H421—C42—H423109.8
C23—C24—H24120.3H422—C42—H423108.2
C25—C24—H24119.9C20—O2—C2115.1 (2)
C24—C25—C26120.4 (3)C30—O3—C3113.2 (2)
C24—C25—H25120.3C1—N1—H11120.6
C26—C25—H25119.3C1—N1—H12119.4
C25—C26—C21120.0 (3)H11—N1—H12120.0
C25—C26—H26120.4C4—N4—C42124.1 (2)
C21—C26—H26119.6C4—N4—C41119.2 (2)
O30—C30—O3121.5 (3)C42—N4—C41116.6 (2)
O1—C1—C2—O2168.2 (2)O30—C30—C31—C36169.8 (3)
N1—C1—C2—O211.0 (4)O3—C30—C31—C369.2 (4)
O1—C1—C2—C366.6 (3)O30—C30—C31—C329.6 (4)
N1—C1—C2—C3114.2 (3)O3—C30—C31—C32171.3 (2)
O2—C2—C3—O359.9 (3)C36—C31—C32—C330.8 (4)
C1—C2—C3—O364.5 (3)C30—C31—C32—C33179.8 (3)
O2—C2—C3—C461.8 (3)C31—C32—C33—C340.8 (5)
C1—C2—C3—C4173.7 (2)C32—C33—C34—C350.1 (5)
O3—C3—C4—O424.8 (4)C33—C34—C35—C361.1 (5)
C2—C3—C4—O495.5 (3)C34—C35—C36—C311.1 (5)
O3—C3—C4—N4157.9 (2)C32—C31—C36—C350.2 (5)
C2—C3—C4—N481.8 (3)C30—C31—C36—C35179.2 (3)
O20—C20—C21—C26175.2 (3)O20—C20—O2—C27.8 (4)
O2—C20—C21—C265.9 (4)C21—C20—O2—C2171.3 (2)
O20—C20—C21—C225.7 (4)C1—C2—O2—C20138.4 (2)
O2—C20—C21—C22173.3 (2)C3—C2—O2—C2098.1 (3)
C26—C21—C22—C231.8 (5)O30—C30—O3—C31.3 (4)
C20—C21—C22—C23179.1 (3)C31—C30—O3—C3177.8 (2)
C21—C22—C23—C240.0 (5)C2—C3—O3—C30164.5 (2)
C22—C23—C24—C251.7 (5)C4—C3—O3—C3071.8 (3)
C23—C24—C25—C261.6 (5)O4—C4—N4—C42176.8 (3)
C24—C25—C26—C210.2 (5)C3—C4—N4—C426.0 (5)
C22—C21—C26—C251.9 (4)O4—C4—N4—C415.9 (5)
C20—C21—C26—C25179.0 (3)C3—C4—N4—C41171.3 (2)
(bn23) (R,R)-(-)-O,O'-Dibenzoyltartaric acid N,N,N'-trimethyldiamide top
Crystal data top
C21H22N2O6F(000) = 420
Mr = 398.41Dx = 1.284 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 8.901 (1) ÅCell parameters from 30 reflections
b = 11.272 (1) Åθ = 8.4–11.3°
c = 10.414 (1) ŵ = 0.10 mm1
β = 99.47 (1)°T = 293 K
V = 1030.62 (18) Å3Prism, colourless
Z = 20.6 × 0.3 × 0.3 mm
Data collection top
KM-4 four circle
diffractometer
Rint = 0.016
Radiation source: fine-focus sealed tubeθmax = 26.1°, θmin = 2.0°
Graphite monochromatorh = 1110
Θ–2Θ scansk = 1313
4029 measured reflectionsl = 012
2127 independent reflections2 standard reflections every 100 reflections
1752 reflections with I > 2σ(I) intensity decay: 1.9%
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)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.084Calculated w = 1/[σ2(Fo2) + (0.0444P)2 + 0.128P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2127 reflectionsΔρmax = 0.14 e Å3
262 parametersΔρmin = 0.13 e Å3
1 restraintAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods
Crystal data top
C21H22N2O6V = 1030.62 (18) Å3
Mr = 398.41Z = 2
Monoclinic, P21Mo Kα radiation
a = 8.901 (1) ŵ = 0.10 mm1
b = 11.272 (1) ÅT = 293 K
c = 10.414 (1) Å0.6 × 0.3 × 0.3 mm
β = 99.47 (1)°
Data collection top
KM-4 four circle
diffractometer
Rint = 0.016
4029 measured reflections2 standard reflections every 100 reflections
2127 independent reflections intensity decay: 1.9%
1752 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0311 restraint
wR(F2) = 0.084H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.14 e Å3
2127 reflectionsΔρmin = 0.13 e Å3
262 parametersAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
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
C10.1058 (2)0.2708 (2)0.6381 (2)0.0370 (5)
C20.0669 (2)0.25491 (19)0.6591 (2)0.0364 (5)
H20.09620.20450.73340.050*
C30.1145 (2)0.19547 (19)0.5419 (2)0.0363 (5)
H30.06130.12160.52440.050*
C40.2872 (3)0.1737 (2)0.5606 (2)0.0420 (5)
C110.3207 (3)0.4017 (3)0.6478 (3)0.0571 (7)
H1110.33880.48460.66000.100*
H1120.35930.35650.71340.100*
H1130.37340.37690.56430.100*
C200.2511 (3)0.3733 (2)0.7927 (2)0.0476 (6)
C210.3356 (3)0.4873 (2)0.7996 (3)0.0474 (6)
C220.4292 (4)0.5129 (3)0.9159 (3)0.0775 (10)
H220.43240.46080.98920.070*
C230.5158 (5)0.6155 (4)0.9255 (4)0.0944 (13)
H230.57950.63481.00640.100*
C240.5114 (4)0.6891 (3)0.8217 (4)0.0872 (11)
H240.57390.75900.82880.100*
C250.4183 (3)0.6637 (3)0.7059 (3)0.0668 (8)
H250.41580.71620.63290.100*
C260.3292 (3)0.5622 (2)0.6949 (3)0.0504 (6)
H260.26360.54410.61460.070*
C300.0511 (3)0.2247 (2)0.3156 (2)0.0415 (5)
C310.0220 (3)0.3132 (2)0.2103 (2)0.0430 (5)
C320.0820 (4)0.2850 (3)0.1003 (2)0.0616 (7)
H320.13230.20940.09410.070*
C330.1131 (5)0.3667 (4)0.0001 (3)0.0844 (11)
H330.18690.34880.07560.100*
C340.0362 (5)0.4733 (4)0.0086 (3)0.0857 (12)
H340.05740.52980.06100.100*
C350.0676 (4)0.5015 (3)0.1170 (3)0.0732 (9)
H350.12210.57530.12080.100*
C360.0959 (3)0.4221 (2)0.2194 (3)0.0528 (6)
H360.16610.44210.29650.070*
C410.5065 (3)0.0604 (3)0.6616 (3)0.0694 (8)
H4110.53000.00640.61120.140*
H4120.53810.04500.75270.140*
H4130.55940.12960.63880.140*
C420.2500 (3)0.0082 (2)0.6873 (3)0.0602 (7)
H4210.30640.08090.70150.140*
H4220.15660.02170.62850.140*
H4230.22540.02020.76820.140*
N10.1586 (2)0.37839 (19)0.6559 (2)0.0439 (5)
H10.09230.43870.67360.050*
N40.3417 (2)0.07952 (19)0.6326 (2)0.0478 (5)
O10.1847 (2)0.18349 (17)0.6098 (2)0.0628 (5)
O20.14441 (16)0.36662 (14)0.68353 (14)0.0380 (3)
O30.07368 (18)0.27469 (14)0.43422 (14)0.0419 (4)
O40.3675 (2)0.24239 (18)0.5121 (2)0.0657 (6)
O200.2724 (3)0.2960 (2)0.8700 (2)0.0960 (10)
O300.0524 (3)0.11960 (17)0.29874 (19)0.0626 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0351 (11)0.0349 (11)0.0409 (11)0.0020 (10)0.0057 (9)0.0019 (10)
C20.0360 (11)0.0287 (11)0.0430 (11)0.0033 (9)0.0020 (9)0.0044 (9)
C30.0371 (11)0.0290 (10)0.0416 (11)0.0008 (9)0.0033 (9)0.0034 (9)
C40.0383 (11)0.0379 (12)0.0506 (12)0.0024 (10)0.0099 (10)0.0002 (11)
C110.0430 (14)0.0563 (17)0.0730 (17)0.0094 (12)0.0121 (12)0.0024 (14)
C200.0477 (12)0.0441 (13)0.0450 (13)0.0010 (11)0.0103 (10)0.0006 (12)
C210.0407 (12)0.0443 (13)0.0535 (14)0.0008 (11)0.0029 (10)0.0075 (12)
C220.084 (2)0.068 (2)0.069 (2)0.0161 (18)0.0203 (17)0.0052 (17)
C230.094 (3)0.076 (2)0.098 (3)0.029 (2)0.029 (2)0.021 (2)
C240.074 (2)0.058 (2)0.126 (3)0.0261 (18)0.009 (2)0.029 (2)
C250.0662 (18)0.0462 (15)0.093 (2)0.0094 (14)0.0265 (16)0.0058 (16)
C260.0434 (12)0.0446 (14)0.0637 (16)0.0005 (11)0.0099 (11)0.0055 (13)
C300.0439 (12)0.0360 (12)0.0446 (13)0.0036 (10)0.0067 (10)0.0036 (10)
C310.0470 (13)0.0426 (13)0.0408 (12)0.0078 (10)0.0111 (10)0.0005 (10)
C320.085 (2)0.0562 (17)0.0413 (13)0.0002 (15)0.0050 (13)0.0037 (13)
C330.119 (3)0.088 (2)0.0416 (15)0.006 (2)0.0020 (16)0.0090 (17)
C340.128 (3)0.077 (2)0.0539 (18)0.013 (2)0.022 (2)0.0260 (18)
C350.097 (2)0.0613 (18)0.067 (2)0.0040 (18)0.0308 (18)0.0196 (16)
C360.0569 (15)0.0475 (14)0.0566 (15)0.0006 (12)0.0168 (12)0.0048 (13)
C410.0381 (13)0.078 (2)0.090 (2)0.0056 (14)0.0043 (13)0.0133 (18)
C420.0502 (15)0.0467 (15)0.085 (2)0.0062 (12)0.0149 (14)0.0253 (15)
N10.0367 (10)0.0387 (10)0.0557 (11)0.0015 (8)0.0061 (8)0.0021 (9)
N40.0336 (10)0.0447 (11)0.0648 (13)0.0032 (9)0.0074 (9)0.0111 (10)
O10.0403 (9)0.0404 (10)0.1072 (16)0.0084 (8)0.0101 (9)0.0078 (11)
O20.0357 (7)0.0346 (8)0.0404 (8)0.0050 (6)0.0031 (6)0.0016 (7)
O30.0544 (9)0.0313 (8)0.0388 (8)0.0050 (7)0.0040 (7)0.0014 (7)
O40.0487 (10)0.0594 (12)0.0933 (14)0.0038 (9)0.0247 (10)0.0235 (11)
O200.120 (2)0.0638 (15)0.0810 (15)0.0290 (14)0.0531 (15)0.0286 (13)
O300.0960 (15)0.0338 (9)0.0554 (11)0.0070 (9)0.0052 (10)0.0041 (8)
Geometric parameters (Å, º) top
C1—O11.217 (3)C25—C261.386 (4)
C1—N11.325 (3)C25—H250.9600
C1—C21.527 (3)C26—H260.9600
C2—O21.438 (3)C30—O301.198 (3)
C2—C31.513 (3)C30—O31.342 (3)
C2—H20.9600C30—C311.474 (3)
C3—O31.433 (2)C31—C321.386 (4)
C3—C41.537 (3)C31—C361.388 (4)
C3—H30.9599C32—C331.387 (4)
C4—O41.218 (3)C32—H320.9600
C4—N41.344 (3)C33—C341.378 (6)
C11—N11.455 (3)C33—H330.9600
C11—H1110.9600C34—C351.374 (6)
C11—H1120.9600C34—H340.9600
C11—H1130.9600C35—C361.383 (4)
C20—O201.180 (3)C35—H350.9600
C20—O21.358 (3)C36—H360.9600
C20—C211.485 (4)C41—N41.464 (3)
C21—C261.373 (4)C41—H4110.9600
C21—C221.383 (4)C41—H4120.9600
C22—C231.384 (5)C41—H4130.9600
C22—H220.9600C42—N41.456 (3)
C23—C241.358 (6)C42—H4210.9600
C23—H230.9600C42—H4220.9600
C24—C251.377 (5)C42—H4230.9600
C24—H240.9600N1—H10.9000
O1—C1—N1124.8 (2)C21—C26—H26120.0
O1—C1—C2117.9 (2)C25—C26—H26120.4
N1—C1—C2117.34 (19)O30—C30—O3123.1 (2)
O2—C2—C3109.89 (17)O30—C30—C31124.4 (2)
O2—C2—C1111.42 (17)O3—C30—C31112.5 (2)
C3—C2—C1110.19 (17)C32—C31—C36120.3 (2)
O2—C2—H2108.4C32—C31—C30118.2 (2)
C3—C2—H2108.2C36—C31—C30121.6 (2)
C1—C2—H2108.6C31—C32—C33119.6 (3)
O3—C3—C2106.68 (16)C31—C32—H32120.0
O3—C3—C4108.51 (17)C33—C32—H32120.4
C2—C3—C4112.07 (17)C34—C33—C32119.6 (3)
O3—C3—H3109.7C34—C33—H33120.2
C2—C3—H3110.0C32—C33—H33120.2
C4—C3—H3109.7C35—C34—C33121.0 (3)
O4—C4—N4123.5 (2)C35—C34—H34119.3
O4—C4—C3119.3 (2)C33—C34—H34119.7
N4—C4—C3117.3 (2)C34—C35—C36119.8 (3)
N1—C11—H111110.7C34—C35—H35120.1
N1—C11—H112109.3C36—C35—H35120.2
H111—C11—H112109.6C35—C36—C31119.7 (3)
N1—C11—H113109.4C35—C36—H36120.2
H111—C11—H113109.6C31—C36—H36120.1
H112—C11—H113108.1N4—C41—H411107.7
O20—C20—O2122.8 (2)N4—C41—H412110.5
O20—C20—C21125.6 (2)H411—C41—H412110.1
O2—C20—C21111.5 (2)N4—C41—H413110.2
C26—C21—C22120.5 (3)H411—C41—H413110.1
C26—C21—C20122.7 (2)H412—C41—H413108.4
C22—C21—C20116.8 (3)N4—C42—H421109.1
C21—C22—C23119.1 (3)N4—C42—H422109.9
C21—C22—H22120.2H421—C42—H422109.8
C23—C22—H22120.7N4—C42—H423109.9
C24—C23—C22120.7 (3)H421—C42—H423109.8
C24—C23—H23119.7H422—C42—H423108.3
C22—C23—H23119.6C1—N1—C11121.9 (2)
C23—C24—C25120.3 (3)C1—N1—H1119.0
C23—C24—H24120.0C11—N1—H1119.1
C25—C24—H24119.7C4—N4—C42125.5 (2)
C24—C25—C26119.9 (3)C4—N4—C41119.2 (2)
C24—C25—H25119.8C42—N4—C41115.3 (2)
C26—C25—H25120.3C20—O2—C2116.43 (18)
C21—C26—C25119.6 (3)C30—O3—C3116.05 (17)
O1—C1—C2—O2176.3 (2)O3—C30—C31—C32143.5 (2)
N1—C1—C2—O25.7 (3)O30—C30—C31—C36144.6 (3)
O1—C1—C2—C354.0 (3)O3—C30—C31—C3636.6 (3)
N1—C1—C2—C3128.0 (2)C36—C31—C32—C330.7 (4)
O2—C2—C3—O359.8 (2)C30—C31—C32—C33179.4 (3)
C1—C2—C3—O363.3 (2)C31—C32—C33—C342.3 (5)
O2—C2—C3—C458.8 (2)C32—C33—C34—C352.0 (6)
C1—C2—C3—C4178.06 (18)C33—C34—C35—C360.0 (6)
O3—C3—C4—O418.2 (3)C34—C35—C36—C311.6 (5)
C2—C3—C4—O499.3 (3)C32—C31—C36—C351.3 (4)
O3—C3—C4—N4162.89 (19)C30—C31—C36—C35178.6 (3)
C2—C3—C4—N479.6 (3)O1—C1—N1—C112.5 (4)
O20—C20—C21—C26165.4 (3)C2—C1—N1—C11175.4 (2)
O2—C20—C21—C2613.8 (3)O4—C4—N4—C42176.8 (3)
O20—C20—C21—C2211.2 (5)C3—C4—N4—C424.3 (4)
O2—C20—C21—C22169.6 (3)O4—C4—N4—C413.5 (4)
C26—C21—C22—C230.3 (5)C3—C4—N4—C41175.3 (2)
C20—C21—C22—C23177.1 (3)O20—C20—O2—C25.8 (4)
C21—C22—C23—C241.2 (6)C21—C20—O2—C2173.40 (18)
C22—C23—C24—C251.1 (6)C3—C2—O2—C20110.7 (2)
C23—C24—C25—C260.3 (5)C1—C2—O2—C20126.8 (2)
C22—C21—C26—C250.5 (4)O30—C30—O3—C35.8 (4)
C20—C21—C26—C25176.0 (3)C31—C30—O3—C3175.35 (18)
C24—C25—C26—C210.5 (4)C2—C3—O3—C30155.48 (18)
O30—C30—C31—C3235.3 (4)C4—C3—O3—C3083.6 (2)
(bom1) (R,R)-(-)-O,O'-Dibenzoyltartaric acid monoamide monomethylester top
Crystal data top
C19H17NO7Dx = 1.306 Mg m3
Mr = 371.34Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 38 reflections
a = 7.193 (1) Åθ = 11.5–13.9°
b = 14.515 (2) ŵ = 0.10 mm1
c = 18.083 (2) ÅT = 293 K
V = 1888.0 (4) Å3Prism, colourless
Z = 40.7 × 0.6 × 0.6 mm
F(000) = 776
Data collection top
KM-4 four circle
diffractometer
Rint = 0.015
Radiation source: fine-focus sealed tubeθmax = 26.1°, θmin = 1.8°
Graphite monochromatorh = 88
Θ–2Θ scansk = 017
3976 measured reflectionsl = 022
2145 independent reflections3 standard reflections every 100 reflections
1709 reflections with I > 2σ(I) intensity decay: 2.1%
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)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090Calculated w = 1/[σ2(Fo2) + (0.0534P)2 + 0.1331P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2145 reflectionsΔρmax = 0.13 e Å3
244 parametersΔρmin = 0.12 e Å3
0 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods
Crystal data top
C19H17NO7V = 1888.0 (4) Å3
Mr = 371.34Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.193 (1) ŵ = 0.10 mm1
b = 14.515 (2) ÅT = 293 K
c = 18.083 (2) Å0.7 × 0.6 × 0.6 mm
Data collection top
KM-4 four circle
diffractometer
Rint = 0.015
3976 measured reflections3 standard reflections every 100 reflections
2145 independent reflections intensity decay: 2.1%
1709 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.13 e Å3
2145 reflectionsΔρmin = 0.12 e Å3
244 parametersAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
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
C10.2644 (3)0.48246 (15)0.53306 (13)0.0544 (5)
C20.1100 (3)0.54720 (15)0.50830 (11)0.0491 (5)
H20.16270.59320.47640.050*
C30.0168 (3)0.59531 (14)0.57273 (11)0.0459 (4)
H30.10910.62740.60110.050*
C40.1229 (3)0.66472 (13)0.54348 (10)0.0433 (4)
C100.3462 (5)0.3313 (2)0.5629 (2)0.0965 (11)
H1010.37120.34380.61870.140*
H1020.30250.26940.55610.140*
H1030.45890.33880.53510.140*
C200.0132 (3)0.46667 (16)0.40236 (11)0.0549 (5)
C210.1376 (3)0.41568 (15)0.36611 (11)0.0553 (6)
C220.1009 (5)0.37242 (19)0.29921 (13)0.0776 (8)
H220.02060.37690.27750.080*
C230.2398 (7)0.3231 (2)0.26407 (16)0.0956 (12)
H230.21530.29290.21790.110*
C240.4139 (6)0.3176 (2)0.29506 (19)0.0939 (11)
H240.51010.28340.27060.110*
C250.4508 (5)0.36073 (18)0.36054 (18)0.0816 (8)
H250.57240.35650.38210.110*
C260.3121 (3)0.40996 (16)0.39596 (13)0.0602 (6)
H260.33880.44060.44180.080*
C300.0187 (3)0.49977 (16)0.68002 (11)0.0530 (5)
C310.0966 (4)0.43965 (14)0.72731 (10)0.0544 (5)
C320.0189 (5)0.40893 (17)0.79307 (12)0.0721 (8)
H320.10690.42470.80560.080*
C330.1251 (7)0.35422 (19)0.84023 (14)0.0858 (11)
H330.07280.33230.88580.110*
C340.2998 (7)0.3321 (2)0.82293 (16)0.0948 (11)
H340.37130.29480.85630.110*
C350.3791 (6)0.3634 (2)0.75829 (17)0.0980 (11)
H350.50520.34750.74640.110*
C360.2779 (5)0.41715 (19)0.71048 (13)0.0743 (8)
H360.33200.43920.66530.080*
N40.2994 (2)0.65145 (13)0.55836 (10)0.0538 (5)
H410.38500.69140.54130.080*
H420.33480.60260.58560.080*
O10.4163 (2)0.50872 (12)0.54705 (12)0.0799 (5)
O20.03430 (18)0.50116 (10)0.46892 (7)0.0493 (3)
O30.07664 (19)0.53076 (9)0.61982 (7)0.0461 (3)
O40.0656 (2)0.72970 (10)0.50694 (10)0.0648 (4)
O100.2082 (2)0.39661 (11)0.53785 (10)0.0655 (4)
O200.1674 (3)0.47659 (17)0.37819 (10)0.0852 (6)
O300.1750 (3)0.52134 (17)0.69146 (10)0.0835 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0388 (10)0.0565 (12)0.0678 (13)0.0090 (9)0.0058 (10)0.0073 (11)
C20.0369 (9)0.0544 (11)0.0559 (11)0.0070 (9)0.0026 (9)0.0090 (9)
C30.0405 (10)0.0493 (10)0.0480 (10)0.0118 (9)0.0072 (9)0.0036 (9)
C40.0469 (10)0.0410 (9)0.0419 (9)0.0100 (9)0.0043 (9)0.0005 (8)
C100.0860 (19)0.0703 (16)0.133 (3)0.0007 (16)0.020 (2)0.0442 (18)
C200.0557 (12)0.0650 (13)0.0439 (10)0.0135 (11)0.0078 (10)0.0087 (10)
C210.0724 (15)0.0508 (11)0.0427 (10)0.0194 (11)0.0043 (10)0.0000 (9)
C220.106 (2)0.0757 (16)0.0507 (13)0.0289 (17)0.0016 (15)0.0036 (12)
C230.162 (4)0.0689 (17)0.0556 (16)0.034 (2)0.032 (2)0.0185 (13)
C240.122 (3)0.0614 (16)0.098 (2)0.0226 (19)0.050 (2)0.0209 (16)
C250.0807 (19)0.0613 (14)0.103 (2)0.0104 (14)0.0280 (17)0.0188 (15)
C260.0659 (14)0.0512 (12)0.0634 (13)0.0105 (12)0.0119 (12)0.0117 (11)
C300.0574 (13)0.0601 (12)0.0415 (10)0.0081 (11)0.0080 (9)0.0021 (10)
C310.0810 (16)0.0452 (10)0.0370 (9)0.0095 (11)0.0040 (11)0.0003 (9)
C320.108 (2)0.0652 (13)0.0425 (11)0.0291 (16)0.0097 (13)0.0010 (11)
C330.158 (3)0.0589 (14)0.0406 (12)0.022 (2)0.0021 (18)0.0094 (11)
C340.162 (4)0.0637 (17)0.0585 (17)0.015 (2)0.021 (2)0.0112 (13)
C350.126 (3)0.094 (2)0.0749 (17)0.036 (2)0.008 (2)0.0226 (16)
C360.098 (2)0.0701 (15)0.0551 (13)0.0198 (16)0.0088 (14)0.0160 (12)
N40.0438 (9)0.0539 (10)0.0638 (11)0.0018 (8)0.0012 (8)0.0193 (8)
O10.0362 (8)0.0715 (10)0.1319 (16)0.0085 (8)0.0060 (10)0.0112 (11)
O20.0402 (7)0.0637 (8)0.0441 (7)0.0032 (7)0.0039 (6)0.0026 (7)
O30.0475 (7)0.0508 (7)0.0399 (6)0.0064 (6)0.0069 (6)0.0088 (6)
O40.0627 (9)0.0527 (9)0.0791 (10)0.0164 (8)0.0013 (8)0.0211 (8)
O100.0562 (8)0.0576 (9)0.0825 (11)0.0083 (7)0.0118 (9)0.0196 (8)
O200.0641 (11)0.1244 (16)0.0672 (10)0.0046 (12)0.0246 (9)0.0009 (11)
O300.0558 (10)0.1283 (17)0.0664 (10)0.0055 (12)0.0205 (9)0.0193 (12)
Geometric parameters (Å, º) top
C1—O11.185 (3)C23—H230.9600
C1—O101.313 (3)C24—C251.365 (4)
C1—C21.522 (3)C24—H240.9600
C2—O21.425 (2)C25—C261.384 (4)
C2—C31.515 (3)C25—H250.9600
C2—H20.9600C26—H260.9601
C3—O31.433 (2)C30—O301.185 (3)
C3—C41.518 (3)C30—O31.363 (2)
C3—H30.9600C30—C311.477 (3)
C4—O41.223 (2)C31—C361.379 (4)
C4—N41.312 (3)C31—C321.388 (3)
C10—O101.445 (3)C32—C331.393 (4)
C10—H1011.0404C32—H320.9600
C10—H1020.9599C33—C341.334 (6)
C10—H1030.9600C33—H330.9599
C20—O201.201 (3)C34—C351.378 (5)
C20—O21.348 (3)C34—H340.9599
C20—C211.468 (3)C35—C361.373 (4)
C21—C261.369 (3)C35—H350.9600
C21—C221.388 (3)C36—H360.9600
C22—C231.384 (5)N4—H410.9001
C22—H220.9599N4—H420.9000
C23—C241.374 (5)
O1—C1—O10125.1 (2)C25—C24—C23120.3 (3)
O1—C1—C2122.5 (2)C25—C24—H24119.8
O10—C1—C2112.38 (17)C23—C24—H24119.9
O2—C2—C3106.14 (15)C24—C25—C26119.9 (3)
O2—C2—C1112.89 (17)C24—C25—H25120.0
C3—C2—C1112.42 (17)C26—C25—H25120.1
O2—C2—H2108.3C21—C26—C25120.6 (2)
C3—C2—H2108.4C21—C26—H26119.7
C1—C2—H2108.5C25—C26—H26119.6
O3—C3—C2111.29 (16)O30—C30—O3122.0 (2)
O3—C3—C4109.32 (15)O30—C30—C31126.0 (2)
C2—C3—C4109.34 (16)O3—C30—C31112.01 (19)
O3—C3—H3108.8C36—C31—C32119.6 (3)
C2—C3—H3109.2C36—C31—C30122.9 (2)
C4—C3—H3108.8C32—C31—C30117.4 (3)
O4—C4—N4123.4 (2)C31—C32—C33119.1 (3)
O4—C4—C3118.51 (18)C31—C32—H32120.3
N4—C4—C3118.13 (17)C33—C32—H32120.5
O10—C10—H101108.0C34—C33—C32120.7 (3)
O10—C10—H102110.4C34—C33—H33119.3
H101—C10—H102110.1C32—C33—H33120.0
O10—C10—H103109.9C33—C34—C35120.7 (3)
H101—C10—H103110.1C33—C34—H34119.5
H102—C10—H103108.4C35—C34—H34119.8
O20—C20—O2121.0 (2)C36—C35—C34120.1 (4)
O20—C20—C21125.5 (2)C36—C35—H35119.8
O2—C20—C21113.51 (19)C34—C35—H35120.1
C26—C21—C22119.4 (3)C35—C36—C31119.8 (3)
C26—C21—C20122.15 (19)C35—C36—H36120.7
C22—C21—C20118.5 (2)C31—C36—H36119.5
C23—C22—C21119.8 (3)C4—N4—H41119.8
C23—C22—H22120.3C4—N4—H42120.2
C21—C22—H22119.9H41—N4—H42120.0
C24—C23—C22120.0 (3)C20—O2—C2115.84 (16)
C24—C23—H23119.7C30—O3—C3117.03 (16)
C22—C23—H23120.2C1—O10—C10115.57 (19)
O1—C1—C2—O2158.0 (2)C24—C25—C26—C210.2 (4)
O10—C1—C2—O223.0 (3)O30—C30—C31—C36179.8 (3)
O1—C1—C2—C381.9 (3)O3—C30—C31—C361.2 (3)
O10—C1—C2—C397.1 (2)O30—C30—C31—C323.4 (4)
O2—C2—C3—O359.67 (19)O3—C30—C31—C32175.63 (19)
C1—C2—C3—O364.2 (2)C36—C31—C32—C331.3 (4)
O2—C2—C3—C461.19 (19)C30—C31—C32—C33178.2 (2)
C1—C2—C3—C4174.94 (15)C31—C32—C33—C340.6 (4)
O3—C3—C4—O4174.23 (17)C32—C33—C34—C350.4 (5)
C2—C3—C4—O463.7 (2)C33—C34—C35—C360.7 (5)
O3—C3—C4—N46.2 (2)C34—C35—C36—C310.1 (5)
C2—C3—C4—N4115.8 (2)C32—C31—C36—C351.0 (4)
O20—C20—C21—C26177.7 (3)C30—C31—C36—C35177.8 (3)
O2—C20—C21—C264.1 (3)O20—C20—O2—C21.5 (3)
O20—C20—C21—C222.0 (4)C21—C20—O2—C2176.83 (17)
O2—C20—C21—C22176.22 (19)C3—C2—O2—C20169.20 (16)
C26—C21—C22—C230.9 (4)C1—C2—O2—C2067.2 (2)
C20—C21—C22—C23179.4 (2)O30—C30—O3—C33.6 (3)
C21—C22—C23—C240.5 (4)C31—C30—O3—C3175.47 (17)
C22—C23—C24—C250.0 (5)C2—C3—O3—C3095.13 (19)
C23—C24—C25—C260.2 (4)C4—C3—O3—C30144.00 (17)
C22—C21—C26—C250.8 (4)O1—C1—O10—C100.5 (4)
C20—C21—C26—C25179.6 (2)C2—C1—O10—C10178.5 (2)
(bom3) (R,R)-(-)-O,O'-Dibenzoyltartaric acid mono(N,N-dimethylamide) monomethylester top
Crystal data top
C21H21NO7F(000) = 420
Mr = 399.39Dx = 1.338 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
a = 8.127 (1) ÅCell parameters from 25 reflections
b = 14.109 (2) Åθ = 12.0–19.9°
c = 8.733 (1) ŵ = 0.85 mm1
β = 97.97 (1)°T = 293 K
V = 991.7 (2) Å3Plate, colourless
Z = 20.8 × 0.4 × 0.3 mm
Data collection top
KM-4 four circle
diffractometer
Rint = 0.030
Radiation source: fine-focus sealed tubeθmax = 64.9°, θmin = 5.1°
Graphite monochromatorh = 99
Θ–2Θ scansk = 1616
3222 measured reflectionsl = 100
3110 independent reflections2 standard reflections every 100 reflections
3016 reflections with I > 2σ(I) intensity decay: 0.8%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.033Calculated w = 1/[σ2(Fo2) + (0.0624P)2 + 0.0749P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.089(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.17 e Å3
3110 reflectionsΔρmin = 0.17 e Å3
263 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0221 (12)
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: 0.28 (15)
Crystal data top
C21H21NO7V = 991.7 (2) Å3
Mr = 399.39Z = 2
Monoclinic, P21Cu Kα radiation
a = 8.127 (1) ŵ = 0.85 mm1
b = 14.109 (2) ÅT = 293 K
c = 8.733 (1) Å0.8 × 0.4 × 0.3 mm
β = 97.97 (1)°
Data collection top
KM-4 four circle
diffractometer
Rint = 0.030
3222 measured reflections2 standard reflections every 100 reflections
3110 independent reflections intensity decay: 0.8%
3016 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.089Δρmax = 0.17 e Å3
S = 1.06Δρmin = 0.17 e Å3
3110 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
263 parametersAbsolute structure parameter: 0.28 (15)
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
C10.3415 (2)0.52804 (12)0.3065 (2)0.0443 (4)
C20.4593 (2)0.50098 (12)0.45013 (17)0.0397 (3)
H20.54440.46030.42100.040*
C30.5404 (2)0.58867 (11)0.53249 (18)0.0390 (3)
H30.59190.62630.46080.040*
C40.67080 (19)0.56146 (11)0.67095 (17)0.0389 (3)
C100.3336 (3)0.5746 (3)0.0468 (2)0.0816 (8)
H1010.25780.62490.06170.110*
H1020.27320.51980.00510.110*
H1030.40660.59420.02480.110*
C200.4407 (2)0.37471 (11)0.62577 (19)0.0441 (4)
C210.3204 (2)0.31809 (11)0.7005 (2)0.0454 (4)
C220.3781 (3)0.26559 (17)0.8303 (3)0.0665 (6)
H220.49390.26720.87120.060*
C230.2693 (4)0.2111 (2)0.9005 (3)0.0846 (8)
H230.30870.17600.99250.090*
C240.1057 (4)0.20666 (18)0.8404 (3)0.0749 (7)
H240.03030.16870.88970.090*
C250.0476 (3)0.25662 (18)0.7103 (3)0.0713 (6)
H250.06750.25220.66730.090*
C260.1548 (3)0.31291 (15)0.6393 (2)0.0579 (5)
H260.11360.34820.54800.060*
C300.4562 (2)0.72413 (11)0.65773 (18)0.0408 (4)
C310.3187 (2)0.76799 (11)0.72762 (19)0.0419 (4)
C320.3574 (3)0.84408 (13)0.8269 (2)0.0508 (4)
H320.46990.86640.84760.060*
C330.2342 (3)0.88773 (16)0.8961 (3)0.0675 (6)
H330.26030.94080.96390.090*
C340.0736 (3)0.85526 (19)0.8658 (3)0.0720 (6)
H340.01200.88470.91480.090*
C350.0343 (3)0.78038 (19)0.7674 (3)0.0695 (6)
H350.07840.75860.74600.090*
C360.1566 (2)0.73613 (15)0.6985 (2)0.0552 (5)
H360.12990.68310.63080.060*
C410.9433 (2)0.50997 (18)0.7719 (2)0.0631 (5)
H4110.91190.45700.79850.110*
H4120.94650.55420.85580.110*
H4131.05260.50560.74260.110*
C420.8695 (2)0.52504 (17)0.4882 (2)0.0611 (5)
H4210.85660.45930.46100.090*
H4220.98250.54400.48590.090*
H4230.79940.56280.41440.090*
N40.82432 (16)0.54087 (11)0.64164 (15)0.0443 (3)
O10.19441 (17)0.52637 (15)0.29316 (18)0.0811 (6)
O20.36355 (15)0.44940 (8)0.54709 (14)0.0436 (3)
O30.40971 (14)0.64119 (8)0.58640 (13)0.0436 (3)
O40.63072 (15)0.56063 (10)0.80091 (13)0.0512 (3)
O100.42805 (15)0.55154 (13)0.19504 (14)0.0599 (4)
O200.58681 (17)0.35861 (10)0.63187 (17)0.0577 (3)
O300.59353 (16)0.75669 (9)0.66181 (15)0.0510 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0407 (8)0.0535 (10)0.0391 (8)0.0013 (7)0.0069 (7)0.0030 (6)
C20.0426 (8)0.0437 (8)0.0339 (8)0.0020 (7)0.0098 (6)0.0016 (6)
C30.0413 (8)0.0411 (8)0.0361 (8)0.0018 (6)0.0100 (6)0.0001 (6)
C40.0442 (8)0.0374 (7)0.0359 (8)0.0013 (6)0.0085 (6)0.0027 (6)
C100.0631 (12)0.140 (3)0.0403 (10)0.0021 (15)0.0020 (9)0.0218 (13)
C200.0531 (10)0.0384 (9)0.0393 (8)0.0017 (7)0.0011 (7)0.0046 (7)
C210.0608 (11)0.0376 (8)0.0377 (8)0.0012 (7)0.0069 (7)0.0029 (6)
C220.0744 (14)0.0705 (13)0.0517 (11)0.0039 (11)0.0019 (10)0.0157 (10)
C230.112 (2)0.0866 (18)0.0546 (13)0.0084 (15)0.0082 (13)0.0281 (12)
C240.0919 (18)0.0693 (14)0.0671 (14)0.0162 (12)0.0240 (13)0.0125 (11)
C250.0653 (13)0.0748 (14)0.0758 (15)0.0129 (11)0.0165 (11)0.0031 (11)
C260.0615 (12)0.0572 (11)0.0543 (11)0.0018 (9)0.0050 (9)0.0093 (9)
C300.0496 (9)0.0369 (7)0.0353 (8)0.0005 (7)0.0037 (7)0.0028 (6)
C310.0501 (9)0.0390 (8)0.0360 (8)0.0033 (7)0.0038 (7)0.0025 (6)
C320.0604 (11)0.0450 (9)0.0472 (10)0.0017 (8)0.0078 (8)0.0030 (7)
C330.0890 (16)0.0554 (11)0.0602 (13)0.0102 (11)0.0178 (11)0.0127 (9)
C340.0729 (14)0.0823 (16)0.0627 (13)0.0262 (12)0.0156 (11)0.0107 (11)
C350.0484 (11)0.0936 (17)0.0664 (13)0.0100 (11)0.0081 (9)0.0084 (12)
C360.0497 (10)0.0614 (11)0.0539 (11)0.0018 (8)0.0055 (8)0.0104 (8)
C410.0523 (11)0.0801 (13)0.0542 (11)0.0112 (10)0.0021 (9)0.0045 (10)
C420.0483 (9)0.0884 (15)0.0493 (10)0.0062 (10)0.0164 (8)0.0005 (9)
N40.0397 (7)0.0540 (8)0.0389 (7)0.0001 (6)0.0042 (6)0.0004 (6)
O10.0434 (7)0.1419 (18)0.0582 (8)0.0016 (9)0.0074 (6)0.0203 (9)
O20.0493 (6)0.0393 (6)0.0439 (6)0.0015 (5)0.0124 (5)0.0028 (5)
O30.0431 (6)0.0401 (6)0.0478 (7)0.0022 (5)0.0074 (5)0.0052 (5)
O40.0619 (7)0.0582 (7)0.0349 (6)0.0063 (6)0.0118 (5)0.0010 (5)
O100.0451 (6)0.0946 (10)0.0400 (6)0.0018 (7)0.0065 (5)0.0154 (7)
O200.0535 (8)0.0563 (8)0.0617 (8)0.0059 (6)0.0022 (6)0.0023 (6)
O300.0476 (7)0.0494 (7)0.0568 (8)0.0069 (5)0.0100 (6)0.0014 (5)
Geometric parameters (Å, º) top
C1—O11.185 (2)C25—C261.387 (3)
C1—O101.320 (2)C25—H250.9600
C1—C21.518 (2)C26—H260.9600
C2—O21.4266 (19)C30—O301.203 (2)
C2—C31.533 (2)C30—O31.355 (2)
C2—H20.9600C30—C311.481 (2)
C3—O31.4276 (19)C31—C361.381 (3)
C3—C41.542 (2)C31—C321.389 (3)
C3—H30.9599C32—C331.383 (3)
C4—O41.2234 (18)C32—H320.9600
C4—N41.340 (2)C33—C341.374 (4)
C10—O101.448 (2)C33—H330.9600
C10—H1010.9601C34—C351.371 (4)
C10—H1020.9600C34—H340.9600
C10—H1030.9600C35—C361.380 (3)
C20—O201.203 (2)C35—H350.9600
C20—O21.362 (2)C36—H360.9600
C20—C211.482 (3)C41—N41.454 (3)
C21—C261.379 (3)C41—H4110.8334
C21—C221.381 (3)C41—H4120.9600
C22—C231.378 (3)C41—H4130.9600
C22—H220.9600C42—N41.455 (2)
C23—C241.361 (4)C42—H4210.9600
C23—H230.9600C42—H4220.9600
C24—C251.365 (4)C42—H4230.9599
C24—H240.9600
O1—C1—O10124.50 (17)C21—C26—C25119.8 (2)
O1—C1—C2126.04 (16)C21—C26—H26120.2
O10—C1—C2109.43 (13)C25—C26—H26119.9
O2—C2—C1106.57 (13)O30—C30—O3122.82 (15)
O2—C2—C3111.57 (12)O30—C30—C31125.33 (15)
C1—C2—C3111.45 (13)O3—C30—C31111.85 (14)
O2—C2—H2108.9C36—C31—C32119.63 (16)
C1—C2—H2109.1C36—C31—C30122.87 (15)
C3—C2—H2109.2C32—C31—C30117.50 (16)
O3—C3—C2106.40 (12)C33—C32—C31120.1 (2)
O3—C3—C4109.42 (12)C33—C32—H32120.0
C2—C3—C4111.78 (12)C31—C32—H32119.9
O3—C3—H3109.8C34—C33—C32119.6 (2)
C2—C3—H3109.8C34—C33—H33120.1
C4—C3—H3109.6C32—C33—H33120.4
O4—C4—N4123.36 (15)C35—C34—C33120.63 (19)
O4—C4—C3119.18 (14)C35—C34—H34119.5
N4—C4—C3117.46 (13)C33—C34—H34119.8
O10—C10—H101108.4C34—C35—C36120.2 (2)
O10—C10—H102109.7C34—C35—H35120.1
H101—C10—H102110.0C36—C35—H35119.7
O10—C10—H103110.4C35—C36—C31119.88 (19)
H101—C10—H103110.0C35—C36—H36120.4
H102—C10—H103108.4C31—C36—H36119.7
O20—C20—O2123.42 (16)N4—C41—H411106.9
O20—C20—C21125.88 (16)N4—C41—H412110.3
O2—C20—C21110.70 (15)H411—C41—H412110.3
C26—C21—C22119.43 (19)N4—C41—H413110.5
C26—C21—C20121.73 (16)H411—C41—H413110.3
C22—C21—C20118.76 (18)H412—C41—H413108.5
C23—C22—C21119.9 (2)N4—C42—H421110.1
C23—C22—H22120.3N4—C42—H422109.9
C21—C22—H22119.8H421—C42—H422109.6
C24—C23—C22120.4 (2)N4—C42—H423109.3
C24—C23—H23119.6H421—C42—H423109.6
C22—C23—H23120.0H422—C42—H423108.2
C23—C24—C25120.3 (2)C4—N4—C41116.85 (14)
C23—C24—H24120.2C4—N4—C42124.73 (14)
C25—C24—H24119.5C41—N4—C42116.69 (15)
C24—C25—C26120.1 (2)C20—O2—C2116.30 (13)
C24—C25—H25119.9C30—O3—C3115.29 (13)
C26—C25—H25120.0C1—O10—C10116.44 (15)
O1—C1—C2—O215.8 (3)O30—C30—C31—C3211.2 (2)
O10—C1—C2—O2162.37 (14)O3—C30—C31—C32168.90 (14)
O1—C1—C2—C3106.1 (2)C36—C31—C32—C330.1 (3)
O10—C1—C2—C375.69 (18)C30—C31—C32—C33179.79 (18)
O2—C2—C3—O353.80 (15)C31—C32—C33—C340.0 (3)
C1—C2—C3—O365.20 (15)C32—C33—C34—C350.3 (4)
O2—C2—C3—C465.60 (16)C33—C34—C35—C360.6 (4)
C1—C2—C3—C4175.40 (13)C34—C35—C36—C310.6 (4)
O3—C3—C4—O420.9 (2)C32—C31—C36—C350.4 (3)
C2—C3—C4—O496.66 (17)C30—C31—C36—C35179.92 (18)
O3—C3—C4—N4158.29 (14)O4—C4—N4—C414.3 (3)
C2—C3—C4—N484.11 (17)C3—C4—N4—C41176.51 (17)
O20—C20—C21—C26151.1 (2)O4—C4—N4—C42168.77 (18)
O2—C20—C21—C2629.0 (2)C3—C4—N4—C4212.0 (2)
O20—C20—C21—C2225.7 (3)O20—C20—O2—C29.5 (2)
O2—C20—C21—C22154.32 (18)C21—C20—O2—C2170.52 (13)
C26—C21—C22—C232.1 (3)C1—C2—O2—C20142.16 (14)
C20—C21—C22—C23178.9 (2)C3—C2—O2—C2095.97 (15)
C21—C22—C23—C241.7 (4)O30—C30—O3—C37.5 (2)
C22—C23—C24—C250.4 (4)C31—C30—O3—C3172.65 (12)
C23—C24—C25—C260.6 (4)C2—C3—O3—C30177.45 (12)
C22—C21—C26—C251.2 (3)C4—C3—O3—C3061.63 (16)
C20—C21—C26—C25177.93 (19)O1—C1—O10—C101.3 (3)
C24—C25—C26—C210.1 (4)C2—C1—O10—C10176.9 (2)
O30—C30—C31—C36169.09 (18)C20—O20—C30i—O30i9.00 (15)
O3—C30—C31—C3610.8 (2)C30i—O30i—C20—O209.46 (16)
Symmetry code: (i) x+1, y1/2, z+1.
(bcn3) N,N-Dimethyl(2R,3S)-2,3-dibenzoyloxy-3-cyanopropanamide top
Crystal data top
C20H18N2O5F(000) = 384
Mr = 366.36Dx = 1.306 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 7.749 (2) ÅCell parameters from 15 reflections
b = 14.144 (4) Åθ = 6.0–17.3°
c = 9.063 (2) ŵ = 0.10 mm1
β = 110.34 (2)°T = 293 K
V = 931.4 (4) Å3Plate, colourless
Z = 20.5 × 0.4 × 0.4 mm
Data collection top
Syntex P21
diffractometer
Rint = 0.033
Radiation source: fine-focus sealed tubeθmax = 27.6°, θmin = 2.4°
Graphite monochromatorh = 09
Θ–2Θ scansk = 1717
3921 measured reflectionsl = 1111
2129 independent reflections2 standard reflections every 100 reflections
1423 reflections with I > 2σ(I) intensity decay: 4.4%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.044Calculated w = 1/[σ2(Fo2) + (0.0503P)2 + 0.092P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.107(Δ/σ)max < 0.001
S = 1.01Δρmax = 0.12 e Å3
2129 reflectionsΔρmin = 0.12 e Å3
245 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.036 (5)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map
Crystal data top
C20H18N2O5V = 931.4 (4) Å3
Mr = 366.36Z = 2
Monoclinic, P21Mo Kα radiation
a = 7.749 (2) ŵ = 0.10 mm1
b = 14.144 (4) ÅT = 293 K
c = 9.063 (2) Å0.5 × 0.4 × 0.4 mm
β = 110.34 (2)°
Data collection top
Syntex P21
diffractometer
Rint = 0.033
3921 measured reflections2 standard reflections every 100 reflections
2129 independent reflections intensity decay: 4.4%
1423 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0441 restraint
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.12 e Å3
2129 reflectionsΔρmin = 0.12 e Å3
245 parametersAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
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
C10.3064 (5)0.6552 (3)0.3428 (4)0.0619 (9)
C20.4712 (5)0.6247 (2)0.4762 (4)0.0547 (8)
H20.54890.58810.43540.050*
C30.5782 (5)0.7097 (2)0.5649 (4)0.0503 (8)
H30.61920.74730.49530.050*
C40.7450 (4)0.6810 (2)0.7081 (3)0.0525 (8)
C200.5104 (6)0.4865 (2)0.6349 (4)0.0561 (8)
C210.4133 (5)0.4224 (2)0.7081 (4)0.0576 (9)
C220.5187 (6)0.3547 (3)0.8138 (4)0.0709 (11)
H220.64890.35100.83550.070*
C230.4340 (8)0.2936 (3)0.8851 (5)0.0831 (13)
H230.50490.24740.95890.120*
C240.2486 (9)0.2974 (3)0.8536 (5)0.0854 (14)
H240.19280.25470.90620.120*
C250.1424 (7)0.3631 (3)0.7467 (6)0.0829 (13)
H250.01180.36540.72370.120*
C260.2253 (6)0.4251 (3)0.6754 (5)0.0697 (10)
H260.15300.47030.60010.070*
C300.5198 (5)0.8502 (2)0.6770 (4)0.0514 (8)
C310.3969 (5)0.9021 (2)0.7418 (4)0.0513 (8)
C320.4721 (6)0.9787 (2)0.8396 (4)0.0600 (9)
H320.59890.99530.86280.070*
C330.3638 (7)1.0297 (3)0.9052 (5)0.0748 (12)
H330.41591.08160.97490.120*
C340.1853 (7)1.0062 (4)0.8714 (5)0.0835 (13)
H340.11151.04270.91640.120*
C350.1098 (6)0.9319 (4)0.7744 (6)0.0939 (15)
H350.01830.91770.74970.120*
C360.2158 (5)0.8782 (3)0.7103 (5)0.0728 (11)
H360.16450.82400.64620.070*
C411.0595 (5)0.6330 (4)0.8212 (4)0.0834 (13)
H4111.05750.66510.91390.120*
H4121.17250.64680.80430.120*
H4131.05330.56590.83500.120*
C420.9216 (5)0.6524 (4)0.5312 (4)0.0750 (11)
H4211.04770.66460.54350.120*
H4220.84220.69620.45760.120*
H4230.88800.58940.49250.120*
N10.1844 (5)0.6776 (3)0.2385 (4)0.0863 (10)
N40.9032 (3)0.6630 (2)0.6848 (3)0.0567 (7)
O20.4026 (3)0.56466 (15)0.5714 (3)0.0576 (6)
O30.4524 (3)0.76432 (14)0.6158 (2)0.0518 (6)
O40.7270 (3)0.6761 (2)0.8372 (2)0.0670 (7)
O200.6591 (4)0.47527 (19)0.6266 (3)0.0713 (7)
O300.6642 (4)0.87897 (18)0.6745 (3)0.0669 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.071 (2)0.066 (2)0.0481 (19)0.0067 (19)0.0202 (18)0.0021 (17)
C20.066 (2)0.0545 (19)0.0482 (17)0.0014 (17)0.0260 (16)0.0009 (15)
C30.0606 (19)0.0448 (18)0.0497 (16)0.0041 (14)0.0245 (15)0.0007 (14)
C40.0632 (19)0.0489 (19)0.0442 (17)0.0047 (16)0.0171 (14)0.0009 (14)
C200.072 (2)0.0429 (18)0.0493 (17)0.0029 (17)0.0158 (17)0.0069 (15)
C210.081 (3)0.0425 (17)0.0469 (18)0.0007 (17)0.0187 (17)0.0046 (14)
C220.096 (3)0.045 (2)0.060 (2)0.0002 (19)0.012 (2)0.0026 (17)
C230.118 (4)0.054 (2)0.058 (2)0.010 (2)0.008 (2)0.0018 (18)
C240.132 (4)0.060 (3)0.065 (3)0.020 (3)0.035 (3)0.003 (2)
C250.096 (3)0.070 (3)0.091 (3)0.010 (2)0.042 (3)0.005 (2)
C260.085 (3)0.054 (2)0.071 (2)0.0052 (19)0.027 (2)0.0120 (19)
C300.056 (2)0.0464 (18)0.0500 (18)0.0047 (16)0.0162 (16)0.0011 (15)
C310.059 (2)0.0418 (18)0.0520 (17)0.0021 (15)0.0186 (15)0.0022 (15)
C320.075 (2)0.0468 (18)0.0604 (19)0.0001 (18)0.0268 (18)0.0043 (17)
C330.104 (4)0.052 (2)0.067 (2)0.010 (2)0.029 (2)0.0002 (19)
C340.092 (3)0.084 (3)0.077 (3)0.029 (3)0.032 (2)0.006 (2)
C350.062 (2)0.120 (4)0.103 (3)0.008 (3)0.033 (2)0.019 (3)
C360.060 (2)0.075 (3)0.084 (3)0.003 (2)0.0249 (19)0.024 (2)
C410.072 (2)0.102 (4)0.066 (2)0.019 (2)0.0106 (19)0.003 (2)
C420.075 (2)0.094 (3)0.063 (2)0.011 (2)0.0336 (17)0.002 (2)
N10.083 (2)0.097 (3)0.0652 (19)0.005 (2)0.0081 (18)0.004 (2)
N40.0582 (15)0.0604 (16)0.0504 (14)0.0058 (15)0.0173 (12)0.0010 (14)
O20.0736 (15)0.0434 (13)0.0604 (13)0.0019 (11)0.0292 (11)0.0011 (11)
O30.0548 (14)0.0435 (12)0.0593 (12)0.0007 (10)0.0227 (11)0.0019 (10)
O40.0838 (15)0.0741 (17)0.0468 (13)0.0097 (14)0.0275 (11)0.0005 (12)
O200.0717 (18)0.0611 (16)0.0831 (17)0.0078 (13)0.0295 (14)0.0006 (13)
O300.0601 (16)0.0615 (16)0.0832 (17)0.0095 (12)0.0301 (13)0.0066 (13)
Geometric parameters (Å, º) top
C1—N11.125 (4)C26—H260.9600
C1—C21.485 (5)C30—O301.198 (4)
C2—O21.438 (4)C30—O31.362 (4)
C2—C31.522 (4)C30—C311.476 (5)
C2—H20.9601C31—C361.374 (5)
C3—O31.440 (4)C31—C321.392 (5)
C3—C41.534 (4)C32—C331.387 (6)
C3—H30.9600C32—H320.9600
C4—O41.228 (4)C33—C341.350 (6)
C4—N41.339 (4)C33—H330.9601
C20—O201.191 (4)C34—C351.365 (7)
C20—O21.385 (4)C34—H340.9599
C20—C211.475 (5)C35—C361.386 (6)
C21—C261.382 (6)C35—H350.9600
C21—C221.399 (5)C36—H360.9600
C22—C231.375 (6)C41—N41.461 (4)
C22—H220.9600C41—H4110.9600
C23—C241.365 (7)C41—H4120.9600
C23—H230.9600C41—H4130.9599
C24—C251.388 (7)C42—N41.455 (4)
C24—H240.9599C42—H4210.9600
C25—C261.375 (6)C42—H4220.9600
C25—H250.9600C42—H4230.9600
N1—C1—C2177.8 (4)O30—C30—C31125.1 (3)
O2—C2—C1105.5 (3)O3—C30—C31113.3 (3)
O2—C2—C3113.4 (2)C36—C31—C32119.7 (3)
C1—C2—C3110.9 (3)C36—C31—C30123.3 (3)
O2—C2—H2109.0C32—C31—C30117.0 (3)
C1—C2—H2108.6C33—C32—C31119.7 (4)
C3—C2—H2109.2C33—C32—H32120.2
O3—C3—C2106.7 (3)C31—C32—H32120.0
O3—C3—C4109.6 (2)C34—C33—C32119.9 (4)
C2—C3—C4112.5 (3)C34—C33—H33120.0
O3—C3—H3109.3C32—C33—H33120.1
C2—C3—H3109.5C33—C34—C35120.8 (4)
C4—C3—H3109.2C33—C34—H34119.1
O4—C4—N4123.6 (3)C35—C34—H34120.2
O4—C4—C3118.7 (3)C34—C35—C36120.6 (4)
N4—C4—C3117.7 (3)C34—C35—H35119.2
O20—C20—O2122.5 (3)C36—C35—H35120.3
O20—C20—C21127.1 (4)C31—C36—C35119.3 (4)
O2—C20—C21110.5 (3)C31—C36—H36120.1
C26—C21—C22119.2 (4)C35—C36—H36120.7
C26—C21—C20123.4 (3)N4—C41—H411110.0
C22—C21—C20117.4 (4)N4—C41—H412109.8
C23—C22—C21119.4 (4)H411—C41—H412109.7
C23—C22—H22120.6N4—C41—H413109.5
C21—C22—H22120.0H411—C41—H413109.7
C24—C23—C22121.2 (4)H412—C41—H413108.2
C24—C23—H23118.6N4—C42—H421107.7
C22—C23—H23120.2N4—C42—H422110.3
C23—C24—C25119.8 (4)H421—C42—H422110.2
C23—C24—H24119.7N4—C42—H423110.0
C25—C24—H24120.5H421—C42—H423110.2
C26—C25—C24119.7 (5)H422—C42—H423108.5
C26—C25—H25120.4C4—N4—C42124.7 (3)
C24—C25—H25119.9C4—N4—C41117.2 (3)
C25—C26—C21120.7 (4)C42—N4—C41116.8 (3)
C25—C26—H26120.4C20—O2—C2115.2 (3)
C21—C26—H26118.8C30—O3—C3113.7 (3)
O30—C30—O3121.6 (3)
O2—C2—C3—O361.3 (3)O3—C30—C31—C32164.8 (3)
C1—C2—C3—O357.3 (3)C36—C31—C32—C330.4 (5)
O2—C2—C3—C459.0 (4)C30—C31—C32—C33179.5 (3)
C1—C2—C3—C4177.5 (3)C31—C32—C33—C341.3 (6)
O3—C3—C4—O424.8 (4)C32—C33—C34—C350.7 (6)
C2—C3—C4—O493.8 (4)C33—C34—C35—C360.9 (8)
O3—C3—C4—N4155.0 (3)C32—C31—C36—C351.1 (6)
C2—C3—C4—N486.4 (4)C30—C31—C36—C35179.0 (4)
O20—C20—C21—C26160.7 (4)C34—C35—C36—C311.8 (7)
O2—C20—C21—C2618.4 (5)O4—C4—N4—C42168.9 (4)
O20—C20—C21—C2218.1 (5)C3—C4—N4—C4211.3 (5)
O2—C20—C21—C22162.8 (3)O4—C4—N4—C412.0 (5)
C26—C21—C22—C231.3 (5)C3—C4—N4—C41178.2 (3)
C20—C21—C22—C23179.8 (3)O20—C20—O2—C28.2 (4)
C21—C22—C23—C240.6 (6)C21—C20—O2—C2170.9 (3)
C22—C23—C24—C250.6 (6)C1—C2—O2—C20141.3 (3)
C23—C24—C25—C261.1 (6)C3—C2—O2—C2097.1 (3)
C24—C25—C26—C210.4 (6)O30—C30—O3—C36.0 (4)
C22—C21—C26—C250.8 (6)C31—C30—O3—C3174.9 (2)
C20—C21—C26—C25179.6 (3)C2—C3—O3—C30170.8 (2)
O30—C30—C31—C36164.0 (4)C4—C3—O3—C3067.2 (3)
O3—C30—C31—C3615.1 (4)C20—O20—C30i—O30i11.3 (3)
O30—C30—C31—C3216.1 (5)C30i—O30i—C20—O2011.7 (3)
Symmetry code: (i) x+1, y1/2, z+1.

Experimental details

(boh1)(boh2)(boh3)(bn13)
Crystal data
Chemical formula(C18H15NO7)·0.15(H2O)(C19H17NO7)·(H2O)C20H19NO7C20H20N2O6
Mr360.01389.35385.36384.38
Crystal system, space groupMonoclinic, P21Orthorhombic, P212121Orthorhombic, P212121Orthorhombic, P212121
Temperature (K)120293120150
a, b, c (Å)7.3930 (4), 19.950 (1), 12.1630 (6)8.7977 (8), 10.752 (1), 20.177 (2)8.6699 (6), 12.0105 (7), 18.657 (1)8.9153 (6), 11.758 (1), 17.976 (1)
α, β, γ (°)90, 97.770 (4), 9090, 90, 9090, 90, 9090, 90, 90
V3)1777.45 (16)1908.6 (3)1942.8 (2)1884.4 (2)
Z4444
Radiation typeMo KαCu KαMo KαMo Kα
µ (mm1)0.110.910.100.10
Crystal size (mm)0.25 × 0.20 × 0.200.3 × 0.2 × 0.10.5 × 0.2 × 0.10.40 × 0.20 × 0.05
Data collection
DiffractometerKuma KM4CCD κ-geometry
diffractometer
KM-4 four circle
diffractometer
Kuma KM4CCD κ-geometry
diffractometer
Kuma KM4CCD κ-geometry
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
11340, 4144, 2463 3086, 2841, 2522 19283, 2726, 2444 12108, 2545, 1697
Rint0.0470.0130.0730.069
(sin θ/λ)max1)0.6490.6010.6670.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.072, 0.84 0.028, 0.076, 1.08 0.051, 0.117, 1.13 0.049, 0.099, 0.98
No. of reflections4144284127262545
No. of parameters489266257253
No. of restraints13000
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.15, 0.160.12, 0.130.22, 0.200.17, 0.23
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 parameter?0.13 (19)??


(bn23)(bom1)(bom3)(bcn3)
Crystal data
Chemical formulaC21H22N2O6C19H17NO7C21H21NO7C20H18N2O5
Mr398.41371.34399.39366.36
Crystal system, space groupMonoclinic, P21Orthorhombic, P212121Monoclinic, P21Monoclinic, P21
Temperature (K)293293293293
a, b, c (Å)8.901 (1), 11.272 (1), 10.414 (1)7.193 (1), 14.515 (2), 18.083 (2)8.127 (1), 14.109 (2), 8.733 (1)7.749 (2), 14.144 (4), 9.063 (2)
α, β, γ (°)90, 99.47 (1), 9090, 90, 9090, 97.97 (1), 9090, 110.34 (2), 90
V3)1030.62 (18)1888.0 (4)991.7 (2)931.4 (4)
Z2422
Radiation typeMo KαMo KαCu KαMo Kα
µ (mm1)0.100.100.850.10
Crystal size (mm)0.6 × 0.3 × 0.30.7 × 0.6 × 0.60.8 × 0.4 × 0.30.5 × 0.4 × 0.4
Data collection
DiffractometerKM-4 four circle
diffractometer
KM-4 four circle
diffractometer
KM-4 four circle
diffractometer
Syntex P21
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4029, 2127, 1752 3976, 2145, 1709 3222, 3110, 3016 3921, 2129, 1423
Rint0.0160.0150.0300.033
(sin θ/λ)max1)0.6180.6180.5870.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.084, 1.04 0.032, 0.090, 1.05 0.033, 0.089, 1.06 0.044, 0.107, 1.01
No. of reflections2127214531102129
No. of parameters262244263245
No. of restraints1011
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.14, 0.130.13, 0.120.17, 0.170.12, 0.12
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 parameter??0.28 (15)?

Computer programs: Kuma KM4CCD software (Kuma Diffraction, 1999), Kuma KM-4 Software (Kuma Diffraction, 1991), SYNTEX Operation Manual, Kuma KM4CCD software, Kuma KM-4 Software, SYNTEX XTL Operation Manual, PRARA, SHELXS86 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), Simens Analytical X-Ray Instruments (1989).

 

Follow Acta Cryst. B
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds