Interplay between dipolar, stacking and hydrogen-bond interactions in the crystal structures of unsymmetrically substituted esters, amides and nitriles of (R,R)-O,O′-dibenzoyltartaric acid

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.

Computing details

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

(boh1) (R,R)-(-)-O,O'-Dibenzoyltartaric acid monoamide

Crystal data

(C18H15NO7)·0.15(H2O)	Z = 4
Mr = 360.01	F(000) = 750
Monoclinic, P21	Dx = 1.345 Mg m^−3
a = 7.3930 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 19.950 (1) Å	µ = 0.11 mm^−1
c = 12.1630 (6) Å	T = 120 K
β = 97.770 (4)°	Prism, colourless
V = 1777.45 (16) Å^3	0.25 × 0.20 × 0.20 mm

Data collection

Kuma KM4CCD κ-geometry diffractometer	2463 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.047
Graphite monochromator	θmax = 27.5°, θmin = 4.1°
ω scans	h = −9→6
11340 measured reflections	k = −22→25
4144 independent reflections	l = −14→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.072	Calculated w = 1/[σ^2(Fo^2) + (0.0337P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.84	(Δ/σ)max < 0.001
4144 reflections	Δρmax = 0.15 e Å^−3
489 parameters	Δρmin = −0.16 e Å^−3
13 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.4587 (4)	0.49114 (15)	0.4556 (3)	0.0302 (7)
C2	0.6632 (4)	0.50111 (15)	0.4608 (2)	0.0275 (7)
H2	0.7030	0.5360	0.5130	0.033*
C3	0.7652 (4)	0.43642 (14)	0.4948 (2)	0.0272 (7)
H3	0.7584	0.4273	0.5718	0.033*
C4	0.9638 (4)	0.44468 (15)	0.4781 (2)	0.0272 (7)
C20	0.6433 (4)	0.58012 (15)	0.3175 (2)	0.0305 (7)
C21	0.7085 (4)	0.60169 (17)	0.2144 (2)	0.0335 (7)
C22	0.6695 (4)	0.66748 (18)	0.1797 (3)	0.0389 (8)
H22	0.5947	0.6954	0.2195	0.047*
C23	0.7407 (5)	0.69266 (19)	0.0877 (3)	0.0503 (10)
H23	0.7161	0.7381	0.0641	0.060*
C24	0.8472 (5)	0.6520 (2)	0.0302 (3)	0.0509 (10)
H24	0.8979	0.6690	−0.0330	0.061*
C25	0.8825 (5)	0.5861 (2)	0.0628 (3)	0.0528 (10)
H25	0.9551	0.5578	0.0220	0.063*
C26	0.8125 (4)	0.56069 (17)	0.1552 (3)	0.0408 (8)
H26	0.8372	0.5152	0.1786	0.049*
C30	0.5861 (3)	0.33600 (14)	0.4786 (2)	0.0255 (6)
C31	0.5094 (3)	0.28404 (14)	0.3997 (2)	0.0245 (6)
C32	0.5026 (4)	0.21836 (15)	0.4367 (3)	0.0322 (7)
H32	0.5439	0.2078	0.5131	0.039*
C33	0.4358 (4)	0.16848 (16)	0.3648 (3)	0.0365 (8)
H33	0.4373	0.1227	0.3898	0.044*
C34	0.3690 (4)	0.18388 (16)	0.2552 (3)	0.0361 (8)
H34	0.3188	0.1492	0.2054	0.043*
C35	0.3714 (4)	0.24930 (16)	0.2192 (3)	0.0356 (8)
H35	0.3242	0.2600	0.1437	0.043*
C36	0.4451 (4)	0.29985 (15)	0.2893 (2)	0.0308 (7)
H36	0.4500	0.3452	0.2631	0.037*
O1	0.3641 (3)	0.47297 (11)	0.37253 (17)	0.0404 (6)
O2	0.7092 (2)	0.51889 (9)	0.35325 (15)	0.0291 (5)
O3	0.6861 (2)	0.38145 (10)	0.42845 (14)	0.0280 (5)
O4	1.0549 (2)	0.48690 (10)	0.53853 (16)	0.0327 (5)
O10	0.4031 (3)	0.50124 (10)	0.55265 (16)	0.0329 (5)
H10	0.285 (5)	0.4947 (19)	0.550 (3)	0.066 (12)*
O20	0.5478 (3)	0.61289 (10)	0.37096 (16)	0.0393 (5)
O30	0.5663 (3)	0.33970 (10)	0.57551 (16)	0.0347 (5)
N4	1.0266 (3)	0.40846 (12)	0.40109 (19)	0.0312 (6)
H41	1.1434	0.4126	0.3884	0.037*
H42	0.9519	0.3790	0.3613	0.037*
C1'	1.0331 (8)	0.3726 (3)	1.0028 (4)	0.0361 (14)	0.70
C1A	0.9993 (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'	0.7813	0.4045	1.0600	0.055*
C3'	0.7230 (4)	0.38591 (16)	0.8905 (2)	0.0382 (8)
H3'	0.7747	0.4260	0.8637	0.046*
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'	0.9281	0.2078	1.3105	0.052*
C23'	0.8527 (5)	0.1125 (2)	1.2624 (3)	0.0517 (10)
H23'	0.9089	0.0913	1.3294	0.062*
C24'	0.7659 (5)	0.07369 (19)	1.1777 (3)	0.0506 (9)
H24'	0.7529	0.0262	1.1874	0.061*
C25'	0.6907 (5)	0.10348 (18)	1.0793 (3)	0.0466 (9)
H25'	0.6285	0.0768	1.0200	0.056*
C26'	0.7068 (4)	0.17220 (17)	1.0653 (3)	0.0406 (8)
H26'	0.6565	0.1925	0.9962	0.049*
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'	1.1031	0.3178	0.6021	0.062*
C33'	1.0675 (5)	0.2202 (3)	0.5525 (3)	0.0638 (12)
H33'	1.1418	0.2221	0.4935	0.077*
C34'	0.9836 (5)	0.1608 (3)	0.5740 (3)	0.0641 (12)
H34'	1.0005	0.1217	0.5304	0.077*
C35'	0.8740 (5)	0.1570 (2)	0.6572 (3)	0.0529 (10)
H35'	0.8175	0.1154	0.6732	0.063*
C36'	0.8450 (4)	0.21371 (18)	0.7195 (3)	0.0411 (8)
H36'	0.7678	0.2118	0.7770	0.049*
O1'	1.1181 (6)	0.3216 (2)	1.0027 (4)	0.0415 (11)	0.70
O1A	1.1081 (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'	1.2422	0.4320	1.0010	0.044*	0.70
O10A	1.0293 (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'	0.2920	0.3747	0.7918	0.049*
H42'	0.4662	0.3505	0.7436	0.049*
O1W	1.3569 (10)	0.4791 (4)	1.1373 (6)	0.049 (2)*	0.30

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0278 (17)	0.0284 (17)	0.0353 (18)	−0.0013 (14)	0.0077 (15)	−0.0064 (15)
C2	0.0246 (16)	0.0333 (18)	0.0257 (16)	−0.0056 (13)	0.0070 (13)	−0.0056 (14)
C3	0.0265 (16)	0.0296 (17)	0.0257 (16)	−0.0086 (13)	0.0050 (13)	−0.0068 (13)
C4	0.0256 (16)	0.0268 (16)	0.0291 (17)	−0.0018 (13)	0.0037 (14)	0.0026 (14)
C20	0.0264 (16)	0.0308 (18)	0.0334 (17)	−0.0029 (14)	0.0009 (14)	−0.0047 (15)
C21	0.0280 (17)	0.042 (2)	0.0293 (16)	−0.0055 (14)	−0.0013 (14)	−0.0004 (15)
C22	0.0319 (18)	0.047 (2)	0.0358 (18)	−0.0026 (16)	−0.0041 (15)	0.0027 (17)
C23	0.044 (2)	0.054 (2)	0.050 (2)	−0.0078 (17)	−0.0070 (19)	0.0150 (19)
C24	0.041 (2)	0.076 (3)	0.034 (2)	−0.009 (2)	−0.0001 (17)	0.014 (2)
C25	0.049 (2)	0.071 (3)	0.039 (2)	−0.002 (2)	0.0102 (18)	0.003 (2)
C26	0.043 (2)	0.043 (2)	0.0371 (19)	−0.0037 (16)	0.0071 (16)	−0.0012 (16)
C30	0.0189 (15)	0.0288 (17)	0.0287 (17)	0.0031 (13)	0.0032 (12)	0.0035 (14)
C31	0.0200 (15)	0.0259 (17)	0.0282 (17)	−0.0038 (13)	0.0057 (13)	−0.0001 (14)
C32	0.0311 (17)	0.0341 (18)	0.0312 (17)	−0.0061 (14)	0.0039 (14)	0.0084 (15)
C33	0.0407 (19)	0.0267 (17)	0.042 (2)	−0.0096 (15)	0.0067 (16)	0.0017 (15)
C34	0.0369 (19)	0.0343 (19)	0.0362 (19)	−0.0064 (15)	0.0015 (15)	−0.0060 (16)
C35	0.043 (2)	0.0336 (18)	0.0269 (17)	−0.0012 (15)	−0.0065 (14)	0.0007 (15)
C36	0.0384 (18)	0.0232 (16)	0.0304 (17)	−0.0024 (14)	0.0033 (14)	0.0035 (14)
O1	0.0275 (12)	0.0599 (16)	0.0343 (13)	−0.0125 (11)	0.0056 (10)	−0.0138 (11)
O2	0.0272 (11)	0.0297 (12)	0.0322 (11)	−0.0012 (9)	0.0111 (9)	−0.0026 (10)
O3	0.0294 (11)	0.0270 (11)	0.0284 (10)	−0.0082 (9)	0.0070 (9)	−0.0028 (9)
O4	0.0250 (11)	0.0361 (12)	0.0374 (12)	−0.0041 (10)	0.0056 (9)	−0.0119 (11)
O10	0.0219 (12)	0.0436 (13)	0.0348 (12)	−0.0020 (10)	0.0100 (10)	−0.0089 (10)
O20	0.0385 (13)	0.0393 (13)	0.0408 (13)	0.0065 (11)	0.0072 (11)	−0.0038 (11)
O30	0.0361 (12)	0.0415 (13)	0.0266 (12)	−0.0063 (10)	0.0045 (9)	0.0027 (10)
N4	0.0266 (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)

C1—O1	1.204 (3)	C1'—O10A	1.640 (10)
C1—O10	1.317 (3)	C1A—O1A	1.187 (15)
C1—C2	1.518 (4)	C1A—O10A	1.346 (13)
C2—O2	1.440 (3)	C1A—C2'	1.367 (11)
C2—C3	1.523 (4)	C1A—O10'	1.450 (12)
C2—H2	0.9614	C1A—O1'	1.558 (11)
C3—O3	1.438 (3)	C2'—O2'	1.436 (4)
C3—C4	1.518 (4)	C2'—C3'	1.524 (4)
C3—H3	0.9614	C2'—H2'	0.9612
C4—O4	1.253 (3)	C3'—O3'	1.440 (3)
C4—N4	1.317 (3)	C3'—C4'	1.527 (4)
C20—O20	1.213 (3)	C3'—H3'	0.9614
C20—O2	1.364 (3)	C4'—O4'	1.235 (3)
C20—C21	1.467 (4)	C4'—N4'	1.317 (4)
C21—C26	1.389 (4)	C20'—O20'	1.217 (3)
C21—C22	1.397 (5)	C20'—O2'	1.362 (3)
C22—C23	1.392 (4)	C20'—C21'	1.475 (4)
C22—H22	0.9614	C21'—C22'	1.393 (4)
C23—C24	1.384 (5)	C21'—C26'	1.396 (4)
C23—H23	0.9613	C22'—C23'	1.381 (5)
C24—C25	1.388 (5)	C22'—H22'	0.9613
C24—H24	0.9613	C23'—C24'	1.375 (5)
C25—C26	1.395 (4)	C23'—H23'	0.9613
C25—H25	0.9612	C24'—C25'	1.384 (5)
C26—H26	0.9613	C24'—H24'	0.9613
C30—O30	1.210 (3)	C25'—C26'	1.389 (5)
C30—O3	1.365 (3)	C25'—H25'	0.9614
C30—C31	1.473 (4)	C26'—H26'	0.9613
C31—C32	1.389 (4)	C30'—O30'	1.209 (4)
C31—C36	1.398 (4)	C30'—O3'	1.365 (4)
C32—C33	1.372 (4)	C30'—C31'	1.477 (5)
C32—H32	0.9613	C31'—C36'	1.381 (4)
C33—C34	1.392 (4)	C31'—C32'	1.403 (4)
C33—H33	0.9613	C32'—C33'	1.384 (5)
C34—C35	1.377 (4)	C32'—H32'	0.9613
C34—H34	0.9613	C33'—C34'	1.379 (6)
C35—C36	1.384 (4)	C33'—H33'	0.9613
C35—H35	0.9613	C34'—C35'	1.381 (5)
C36—H36	0.9613	C34'—H34'	0.9614
O10—H10	0.88 (4)	C35'—C36'	1.395 (5)
N4—H41	0.9011	C35'—H35'	0.9613
N4—H42	0.9012	C36'—H36'	0.9612
C1'—C1A	0.573 (10)	O1'—O1A	0.529 (10)
C1'—O1A	0.982 (12)	O10'—O10A	1.060 (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—O10	125.6 (3)	O10A—C1A—O10'	44.4 (5)
O1—C1—C2	122.5 (3)	C2'—C1A—O10'	121.1 (8)
O10—C1—C2	111.8 (3)	C1'—C1A—O1'	42.1 (12)
O2—C2—C1	110.5 (2)	O1A—C1A—O1'	15.9 (6)
O2—C2—C3	106.6 (2)	O10A—C1A—O1'	134.8 (9)
C1—C2—C3	110.7 (2)	C2'—C1A—O1'	114.3 (8)
O2—C2—H2	109.5	O10'—C1A—O1'	96.9 (6)
C1—C2—H2	109.7	C1A—C2'—O2'	109.6 (5)
C3—C2—H2	109.8	C1A—C2'—C3'	124.1 (5)
O3—C3—C4	109.6 (2)	O2'—C2'—C3'	105.7 (3)
O3—C3—C2	110.2 (2)	C1A—C2'—C1'	20.0 (4)
C4—C3—C2	108.9 (2)	O2'—C2'—C1'	109.6 (3)
O3—C3—H3	109.4	C3'—C2'—C1'	106.7 (3)
C4—C3—H3	109.2	C1A—C2'—H2'	94.6
C2—C3—H3	109.6	O2'—C2'—H2'	110.5
O4—C4—N4	125.0 (3)	C3'—C2'—H2'	111.8
O4—C4—C3	116.6 (2)	C1'—C2'—H2'	112.2
N4—C4—C3	118.4 (3)	O3'—C3'—C2'	109.3 (2)
O20—C20—O2	121.3 (3)	O3'—C3'—C4'	109.3 (2)
O20—C20—C21	125.6 (3)	C2'—C3'—C4'	112.3 (3)
O2—C20—C21	113.0 (3)	O3'—C3'—H3'	108.5
C26—C21—C22	120.2 (3)	C2'—C3'—H3'	108.4
C26—C21—C20	122.6 (3)	C4'—C3'—H3'	108.9
C22—C21—C20	117.1 (3)	O4'—C4'—N4'	124.5 (3)
C23—C22—C21	119.8 (3)	O4'—C4'—C3'	118.7 (3)
C23—C22—H22	120.1	N4'—C4'—C3'	116.7 (3)
C21—C22—H22	120.1	O20'—C20'—O2'	121.4 (3)
C24—C23—C22	119.8 (3)	O20'—C20'—C21'	126.4 (3)
C24—C23—H23	119.9	O2'—C20'—C21'	112.2 (3)
C22—C23—H23	120.3	C22'—C21'—C26'	119.7 (3)
C23—C24—C25	120.5 (3)	C22'—C21'—C20'	118.3 (3)
C23—C24—H24	120.5	C26'—C21'—C20'	122.0 (3)
C25—C24—H24	118.9	C23'—C22'—C21'	119.4 (3)
C24—C25—C26	119.9 (3)	C23'—C22'—H22'	120.7
C24—C25—H25	120.4	C21'—C22'—H22'	119.9
C26—C25—H25	119.7	C24'—C23'—C22'	121.2 (3)
C21—C26—C25	119.7 (3)	C24'—C23'—H23'	119.5
C21—C26—H26	119.9	C22'—C23'—H23'	119.3
C25—C26—H26	120.4	C23'—C24'—C25'	119.9 (3)
O30—C30—O3	122.6 (3)	C23'—C24'—H24'	120.5
O30—C30—C31	126.2 (3)	C25'—C24'—H24'	119.6
O3—C30—C31	111.1 (2)	C24'—C25'—C26'	119.9 (3)
C32—C31—C36	120.1 (3)	C24'—C25'—H25'	120.5
C32—C31—C30	118.7 (3)	C26'—C25'—H25'	119.6
C36—C31—C30	121.2 (3)	C25'—C26'—C21'	119.9 (3)
C33—C32—C31	120.2 (3)	C25'—C26'—H26'	119.6
C33—C32—H32	119.8	C21'—C26'—H26'	120.4
C31—C32—H32	120.0	O30'—C30'—O3'	121.7 (3)
C32—C33—C34	120.1 (3)	O30'—C30'—C31'	125.8 (3)
C32—C33—H33	119.9	O3'—C30'—C31'	112.5 (3)
C34—C33—H33	120.0	C36'—C31'—C32'	120.1 (3)
C35—C34—C33	119.7 (3)	C36'—C31'—C30'	122.2 (3)
C35—C34—H34	120.2	C32'—C31'—C30'	117.7 (3)
C33—C34—H34	120.1	C33'—C32'—C31'	119.9 (4)
C34—C35—C36	121.0 (3)	C33'—C32'—H32'	120.4
C34—C35—H35	119.7	C31'—C32'—H32'	119.7
C36—C35—H35	119.3	C34'—C33'—C32'	119.7 (4)
C35—C36—C31	118.8 (3)	C34'—C33'—H33'	119.5
C35—C36—H36	120.7	C32'—C33'—H33'	120.7
C31—C36—H36	120.5	C33'—C34'—C35'	120.7 (4)
C20—O2—C2	113.1 (2)	C33'—C34'—H34'	119.9
C30—O3—C3	117.4 (2)	C35'—C34'—H34'	119.4
C1—O10—H10	112 (2)	C34'—C35'—C36'	120.1 (4)
C4—N4—H41	120.6	C34'—C35'—H35'	120.7
C4—N4—H42	119.4	C36'—C35'—H35'	119.2
H41—N4—H42	120.0	C31'—C36'—C35'	119.5 (3)
C1A—C1'—O1A	96.0 (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'—C1A	38.0 (17)
O1A—C1'—O10'	120.4 (9)	C1'—O1'—C1A	18.7 (5)
O1'—C1'—O10'	126.0 (5)	O1'—O1A—C1'	100.5 (19)
C1A—C1'—C2'	54.9 (14)	O1'—O1A—C1A	126 (2)
O1A—C1'—C2'	119.1 (9)	C1'—O1A—C1A	28.7 (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'—O10A	50.1 (14)	O10A—O10'—C1'	85.9 (5)
O1A—C1'—O10A	118.8 (8)	O10A—O10'—C1A	62.6 (5)
O1'—C1'—O10A	141.7 (5)	C1'—O10'—C1A	23.3 (4)
O10'—C1'—O10A	40.1 (3)	O10A—O10'—H10'	127.7
C2'—C1'—O10A	84.4 (4)	C1'—O10'—H10'	109.8
C1'—C1A—O1A	55.4 (13)	C1A—O10'—H10'	122.0
C1'—C1A—O10A	110.8 (18)	O10'—O10A—C1A	73.0 (7)
O1A—C1A—O10A	128.3 (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—O2	28.5 (4)	C21'—C22'—C23'—C24'	−0.1 (5)
O10—C1—C2—O2	−154.9 (2)	C22'—C23'—C24'—C25'	−0.9 (5)
O1—C1—C2—C3	−89.5 (3)	C23'—C24'—C25'—C26'	1.5 (5)
O10—C1—C2—C3	87.2 (3)	C24'—C25'—C26'—C21'	−1.1 (5)
O2—C2—C3—O3	−71.0 (2)	C22'—C21'—C26'—C25'	0.0 (5)
C1—C2—C3—O3	49.3 (3)	C20'—C21'—C26'—C25'	178.4 (3)
O2—C2—C3—C4	49.2 (3)	O30'—C30'—C31'—C36'	166.6 (3)
C1—C2—C3—C4	169.5 (2)	O3'—C30'—C31'—C36'	−14.5 (4)
O3—C3—C4—O4	−173.7 (2)	O30'—C30'—C31'—C32'	−14.4 (5)
C2—C3—C4—O4	65.7 (3)	O3'—C30'—C31'—C32'	164.6 (3)
O3—C3—C4—N4	7.4 (3)	C36'—C31'—C32'—C33'	0.5 (5)
C2—C3—C4—N4	−113.1 (3)	C30'—C31'—C32'—C33'	−178.5 (3)
O20—C20—C21—C26	−177.7 (3)	C31'—C32'—C33'—C34'	−0.8 (5)
O2—C20—C21—C26	5.6 (4)	C32'—C33'—C34'—C35'	0.1 (5)
O20—C20—C21—C22	5.4 (4)	C33'—C34'—C35'—C36'	0.9 (5)
O2—C20—C21—C22	−171.2 (3)	C32'—C31'—C36'—C35'	0.4 (5)
C26—C21—C22—C23	−2.3 (4)	C30'—C31'—C36'—C35'	179.5 (3)
C20—C21—C22—C23	174.7 (3)	C34'—C35'—C36'—C31'	−1.2 (5)
C21—C22—C23—C24	1.1 (5)	C1A—C1'—O1'—O1A	−28 (3)
C22—C23—C24—C25	0.5 (5)	O10'—C1'—O1'—O1A	86 (2)
C23—C24—C25—C26	−0.9 (5)	C2'—C1'—O1'—O1A	−93 (2)
C22—C21—C26—C25	1.9 (5)	O10A—C1'—O1'—O1A	33 (2)
C20—C21—C26—C25	−174.8 (3)	O1A—C1'—O1'—C1A	28 (3)
C24—C25—C26—C21	−0.3 (5)	O10'—C1'—O1'—C1A	114 (2)
O30—C30—C31—C32	−38.1 (4)	C2'—C1'—O1'—C1A	−64.5 (18)
O3—C30—C31—C32	141.9 (2)	O10A—C1'—O1'—C1A	61.4 (17)
O30—C30—C31—C36	142.2 (3)	C1'—C1A—O1'—O1A	142 (3)
O3—C30—C31—C36	−37.8 (3)	O10A—C1A—O1'—O1A	73 (3)
C36—C31—C32—C33	1.2 (4)	C2'—C1A—O1'—O1A	−132 (3)
C30—C31—C32—C33	−178.5 (3)	O10'—C1A—O1'—O1A	99 (3)
C31—C32—C33—C34	−2.1 (4)	O1A—C1A—O1'—C1'	−142 (3)
C32—C33—C34—C35	0.4 (4)	O10A—C1A—O1'—C1'	−69.4 (18)
C33—C34—C35—C36	2.3 (5)	C2'—C1A—O1'—C1'	85.8 (18)
C34—C35—C36—C31	−3.1 (5)	O10'—C1A—O1'—C1'	−43.0 (15)
C32—C31—C36—C35	1.4 (4)	C1A—O1'—O1A—C1'	−14.2 (13)
C30—C31—C36—C35	−178.9 (3)	C1'—O1'—O1A—C1A	14.2 (13)
O20—C20—O2—C2	−3.7 (4)	C1A—C1'—O1A—O1'	156 (2)
C21—C20—O2—C2	173.1 (2)	O10'—C1'—O1A—O1'	−110.6 (17)
C1—C2—O2—C20	66.4 (3)	C2'—C1'—O1A—O1'	102.7 (18)
C3—C2—O2—C20	−173.1 (2)	O10A—C1'—O1A—O1'	−157.1 (15)
O30—C30—O3—C3	−1.8 (4)	O1'—C1'—O1A—C1A	−156 (2)
C31—C30—O3—C3	178.2 (2)	O10'—C1'—O1A—C1A	93.8 (16)
C4—C3—O3—C30	133.0 (2)	C2'—C1'—O1A—C1A	−52.9 (15)
C2—C3—O3—C30	−107.3 (2)	O10A—C1'—O1A—C1A	47.3 (14)
O1'—C1'—C1A—O1A	11.9 (10)	C1'—C1A—O1A—O1'	−30 (3)
O10'—C1'—C1A—O1A	−120.6 (10)	O10A—C1A—O1A—O1'	−120 (2)
C2'—C1'—C1A—O1A	121.6 (11)	C2'—C1A—O1A—O1'	55 (3)
O10A—C1'—C1A—O1A	−122.9 (12)	O10'—C1A—O1A—O1'	−83 (3)
O1A—C1'—C1A—O10A	122.9 (12)	O10A—C1A—O1A—C1'	−90.3 (19)
O1'—C1'—C1A—O10A	134.8 (10)	C2'—C1A—O1A—C1'	84.9 (18)
O10'—C1'—C1A—O10A	2.3 (12)	O10'—C1A—O1A—C1'	−53.1 (13)
C2'—C1'—C1A—O10A	−115.5 (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'—O10A	−2.8 (15)
C2'—C1'—C1A—O1'	109.7 (11)	O1A—C1'—O10'—O10A	−99.8 (10)
O10A—C1'—C1A—O1'	−134.8 (10)	O1'—C1'—O10'—O10A	−130.0 (7)
C1'—C1A—C2'—O2'	93.6 (17)	C2'—C1'—O10'—O10A	48.8 (6)
O1A—C1A—C2'—O2'	35.5 (13)	O1A—C1'—O10'—C1A	−97.1 (16)
O10A—C1A—C2'—O2'	−148.5 (6)	O1'—C1'—O10'—C1A	−127.2 (17)
O10'—C1A—C2'—O2'	165.0 (7)	C2'—C1'—O10'—C1A	51.6 (14)
O1'—C1A—C2'—O2'	49.7 (8)	O10A—C1'—O10'—C1A	2.8 (15)
C1'—C1A—C2'—C3'	−32 (2)	C1'—C1A—O10'—O10A	176.9 (17)
O1A—C1A—C2'—C3'	−90.5 (12)	O1A—C1A—O10'—O10A	−137.3 (10)
O10A—C1A—C2'—C3'	85.5 (8)	C2'—C1A—O10'—O10A	82.9 (10)
O10'—C1A—C2'—C3'	38.9 (11)	O1'—C1A—O10'—O10A	−153.2 (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—C1A	1.2 (7)
O1A—C1'—C2'—C1A	75.8 (19)	C1A—O10'—O10A—C1'	−1.2 (7)
O1'—C1'—C2'—C1A	105.5 (19)	C1'—C1A—O10A—O10'	−3.0 (16)
O10'—C1'—C2'—C1A	−73.3 (17)	O1A—C1A—O10A—O10'	58.6 (12)
O10A—C1'—C2'—C1A	−44.1 (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—C1A	−72.3 (18)
C1A—C2'—C3'—O3'	76.5 (7)	O1'—C1'—O10A—C1A	−88.1 (19)
O2'—C2'—C3'—O3'	−51.3 (3)	O10'—C1'—O10A—C1A	−176.4 (19)
C1'—C2'—C3'—O3'	65.4 (3)	C2'—C1'—O10A—C1A	47.9 (17)
C1A—C2'—C3'—C4'	−162.1 (6)	H2—C2—O2—C20	−54.5
O2'—C2'—C3'—C4'	70.2 (3)	H3—C3—O3—C30	13.3
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—O4	−6.5
O3'—C3'—C4'—N4'	−21.7 (4)	H2—C2—C20—O20	−53.3
C2'—C3'—C4'—N4'	−143.2 (3)	H3—C3—C1—O10	11.2
O20'—C20'—C21'—C22'	−4.8 (5)	H3—C3—C30—O30	11.2
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)

Crystal data

(C19H17NO7)·(H2O)	Dx = 1.355 Mg m^−3
Mr = 389.35	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121	Cell parameters from 40 reflections
a = 8.7977 (8) Å	θ = 12.8–23.9°
b = 10.752 (1) Å	µ = 0.91 mm^−1
c = 20.177 (2) Å	T = 293 K
V = 1908.6 (3) Å^3	Prism, colourless
Z = 4	0.3 × 0.2 × 0.1 mm
F(000) = 816

Data collection

KM-4 four circle diffractometer	Rint = 0.013
Radiation source: fine-focus sealed tube	θmax = 67.9°, θmin = 4.4°
Graphite monochromator	h = −9→9
Θ–2Θ scans	k = 0→12
3086 measured reflections	l = 0→24
2841 independent reflections	2 standard reflections every 100 reflections
2522 reflections with I > 2σ(I)	intensity decay: 2.8%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.028	Calculated w = 1/[σ^2(Fo^2) + (0.0425P)^2 + 0.1715P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.076	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.12 e Å^−3
2841 reflections	Δρmin = −0.13 e Å^−3
266 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0052 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.13 (19)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2694 (2)	0.45907 (18)	0.76410 (9)	0.0447 (4)
C2	0.0993 (2)	0.47894 (16)	0.76102 (9)	0.0420 (4)
H2	0.0506	0.4001	0.7542	0.040*
C3	0.0414 (2)	0.53418 (16)	0.82515 (8)	0.0415 (4)
H3	0.0737	0.4808	0.8606	0.040*
C4	−0.1314 (2)	0.54050 (17)	0.82723 (8)	0.0433 (4)
C20	0.0747 (2)	0.51075 (17)	0.64673 (9)	0.0448 (4)
C21	0.0155 (2)	0.58988 (17)	0.59351 (10)	0.0450 (4)
C22	0.0347 (3)	0.5498 (2)	0.52880 (10)	0.0635 (6)
H22	0.0898	0.4746	0.5198	0.070*
C23	−0.0293 (4)	0.6162 (2)	0.47761 (11)	0.0739 (7)
H23	−0.0133	0.5899	0.4327	0.080*
C24	−0.1134 (3)	0.7205 (2)	0.49004 (11)	0.0652 (6)
H24	−0.1601	0.7647	0.4541	0.080*
C25	−0.1299 (3)	0.7625 (2)	0.55403 (11)	0.0661 (6)
H25	−0.1867	0.8369	0.5626	0.080*
C26	−0.0656 (3)	0.69728 (18)	0.60571 (10)	0.0574 (5)
H26	−0.0784	0.7261	0.6504	0.070*
C30	0.1956 (2)	0.66716 (19)	0.89077 (9)	0.0500 (5)
C31	0.2653 (2)	0.79004 (18)	0.89572 (10)	0.0480 (5)
C32	0.3324 (3)	0.8245 (2)	0.95496 (12)	0.0769 (7)
H32	0.3321	0.7686	0.9921	0.070*
C33	0.4004 (4)	0.9404 (3)	0.95987 (17)	0.0975 (10)
H33	0.4424	0.9668	1.0015	0.110*
C34	0.4044 (3)	1.0181 (3)	0.90694 (18)	0.0922 (9)
H34	0.4565	1.0962	0.9107	0.110*
C35	0.3402 (3)	0.9847 (2)	0.84839 (14)	0.0747 (7)
H35	0.3426	1.0411	0.8115	0.110*
C36	0.2694 (2)	0.87053 (19)	0.84221 (11)	0.0531 (5)
H36	0.2235	0.8464	0.8010	0.070*
C41	−0.3574 (3)	0.6626 (2)	0.85022 (13)	0.0707 (6)
H411	−0.4072	0.6078	0.8196	0.140*
H412	−0.3857	0.7472	0.8413	0.140*
H413	−0.3869	0.6428	0.8948	0.140*
N4	−0.19436 (18)	0.64710 (15)	0.84234 (8)	0.0506 (4)
H4	−0.1337	0.7135	0.8486	0.070*
O1	0.36154 (16)	0.53294 (13)	0.74493 (8)	0.0650 (4)
O2	0.05716 (15)	0.56050 (10)	0.70785 (6)	0.0451 (3)
O3	0.10880 (14)	0.65382 (10)	0.83588 (6)	0.0427 (3)
O4	−0.20046 (17)	0.44394 (13)	0.81663 (8)	0.0647 (4)
O10	0.30009 (18)	0.35320 (13)	0.79278 (7)	0.0567 (4)
H10	0.411 (3)	0.341 (2)	0.7946 (12)	0.076 (7)*
O20	0.1307 (2)	0.40943 (13)	0.63916 (7)	0.0606 (4)
O30	0.2121 (3)	0.58422 (17)	0.92939 (10)	0.1019 (8)
O1W	0.57215 (18)	0.27430 (15)	0.81209 (8)	0.0558 (4)
H1W	0.649 (3)	0.328 (3)	0.8139 (12)	0.077 (8)*
H2W	0.605 (4)	0.206 (3)	0.7906 (15)	0.105 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0488 (11)	0.0359 (10)	0.0495 (9)	0.0006 (9)	0.0035 (8)	0.0014 (9)
C2	0.0454 (10)	0.0320 (9)	0.0485 (9)	−0.0013 (8)	−0.0040 (8)	0.0037 (8)
C3	0.0456 (10)	0.0344 (9)	0.0445 (9)	−0.0052 (8)	−0.0048 (8)	0.0048 (8)
C4	0.0454 (10)	0.0403 (10)	0.0441 (9)	−0.0065 (9)	0.0008 (8)	0.0012 (8)
C20	0.0483 (10)	0.0373 (10)	0.0488 (10)	0.0019 (9)	0.0077 (8)	−0.0020 (8)
C21	0.0537 (11)	0.0385 (9)	0.0428 (9)	−0.0014 (8)	0.0056 (8)	0.0005 (8)
C22	0.0854 (16)	0.0560 (12)	0.0491 (11)	0.0101 (12)	0.0136 (11)	−0.0027 (10)
C23	0.109 (2)	0.0724 (16)	0.0401 (10)	0.0027 (15)	0.0038 (12)	0.0010 (10)
C24	0.0875 (17)	0.0551 (13)	0.0530 (12)	−0.0041 (13)	−0.0093 (11)	0.0114 (10)
C25	0.0911 (17)	0.0453 (12)	0.0617 (13)	0.0117 (12)	−0.0117 (12)	0.0027 (10)
C26	0.0786 (14)	0.0468 (11)	0.0470 (10)	0.0105 (11)	−0.0030 (10)	−0.0043 (9)
C30	0.0545 (11)	0.0498 (11)	0.0456 (10)	−0.0001 (10)	−0.0111 (9)	0.0001 (10)
C31	0.0405 (10)	0.0483 (11)	0.0553 (11)	0.0002 (8)	−0.0053 (8)	−0.0095 (9)
C32	0.0945 (19)	0.0668 (15)	0.0694 (14)	−0.0060 (15)	−0.0277 (13)	−0.0105 (12)
C33	0.108 (3)	0.0798 (19)	0.104 (2)	−0.0200 (18)	−0.0438 (19)	−0.0300 (18)
C34	0.0836 (19)	0.0637 (16)	0.129 (2)	−0.0244 (15)	−0.0124 (18)	−0.0186 (17)
C35	0.0723 (16)	0.0578 (14)	0.0939 (18)	−0.0213 (12)	0.0072 (14)	−0.0025 (13)
C36	0.0490 (12)	0.0494 (11)	0.0610 (12)	−0.0060 (9)	0.0058 (9)	−0.0048 (10)
C41	0.0478 (12)	0.0688 (15)	0.0955 (16)	0.0017 (11)	0.0092 (12)	0.0011 (13)
N4	0.0411 (8)	0.0424 (9)	0.0682 (10)	−0.0025 (7)	0.0033 (8)	−0.0025 (8)
O1	0.0504 (8)	0.0506 (8)	0.0941 (11)	−0.0062 (7)	0.0044 (8)	0.0171 (8)
O2	0.0561 (8)	0.0371 (7)	0.0420 (6)	0.0054 (6)	−0.0017 (6)	0.0001 (5)
O3	0.0454 (7)	0.0360 (7)	0.0468 (6)	−0.0060 (5)	−0.0079 (5)	0.0018 (5)
O4	0.0562 (9)	0.0484 (8)	0.0894 (11)	−0.0158 (7)	0.0044 (8)	−0.0117 (8)
O10	0.0485 (9)	0.0456 (8)	0.0760 (9)	0.0064 (7)	0.0036 (7)	0.0169 (7)
O20	0.0786 (10)	0.0441 (8)	0.0590 (8)	0.0146 (7)	0.0083 (7)	−0.0016 (6)
O30	0.157 (2)	0.0641 (11)	0.0847 (12)	−0.0277 (12)	−0.0672 (13)	0.0241 (10)
O1W	0.0462 (8)	0.0468 (8)	0.0744 (10)	−0.0027 (7)	0.0012 (7)	−0.0050 (7)

Geometric parameters (Å, º)

C1—O1	1.199 (2)	C26—H26	0.9601
C1—O10	1.305 (2)	C30—O30	1.193 (2)
C1—C2	1.513 (3)	C30—O3	1.353 (2)
C2—O2	1.434 (2)	C30—C31	1.460 (3)
C2—C3	1.512 (2)	C31—C32	1.384 (3)
C2—H2	0.9599	C31—C36	1.384 (3)
C3—O3	1.433 (2)	C32—C33	1.386 (4)
C3—C4	1.522 (3)	C32—H32	0.9600
C3—H3	0.9600	C33—C34	1.356 (4)
C4—O4	1.222 (2)	C33—H33	0.9599
C4—N4	1.309 (2)	C34—C35	1.358 (4)
C20—O20	1.205 (2)	C34—H34	0.9600
C20—O2	1.353 (2)	C35—C36	1.382 (3)
C20—C21	1.465 (3)	C35—H35	0.9599
C21—C26	1.380 (3)	C36—H36	0.9600
C21—C22	1.385 (3)	C41—N4	1.453 (3)
C22—C23	1.376 (3)	C41—H411	0.9599
C22—H22	0.9599	C41—H412	0.9599
C23—C24	1.366 (3)	C41—H413	0.9599
C23—H23	0.9600	N4—H4	0.9000
C24—C25	1.375 (3)	O10—H10	0.99 (3)
C24—H24	0.9600	O1W—H1W	0.89 (3)
C25—C26	1.378 (3)	O1W—H2W	0.90 (3)
C25—H25	0.9600
O1—C1—O10	125.53 (18)	C25—C26—H26	119.9
O1—C1—C2	124.18 (17)	C21—C26—H26	119.9
O10—C1—C2	110.23 (16)	O30—C30—O3	121.61 (18)
O2—C2—C3	108.23 (14)	O30—C30—C31	125.49 (18)
O2—C2—C1	111.88 (15)	O3—C30—C31	112.89 (16)
C3—C2—C1	110.70 (15)	C32—C31—C36	119.7 (2)
O2—C2—H2	108.5	C32—C31—C30	118.7 (2)
C3—C2—H2	108.6	C36—C31—C30	121.56 (18)
C1—C2—H2	108.8	C31—C32—C33	119.1 (2)
O3—C3—C2	110.03 (14)	C31—C32—H32	120.4
O3—C3—C4	111.65 (15)	C33—C32—H32	120.5
C2—C3—C4	112.18 (14)	C34—C33—C32	120.6 (2)
O3—C3—H3	107.6	C34—C33—H33	119.7
C2—C3—H3	107.6	C32—C33—H33	119.6
C4—C3—H3	107.5	C33—C34—C35	120.8 (2)
O4—C4—N4	125.03 (17)	C33—C34—H34	119.3
O4—C4—C3	117.00 (17)	C35—C34—H34	119.9
N4—C4—C3	117.92 (16)	C34—C35—C36	120.0 (3)
O20—C20—O2	121.28 (17)	C34—C35—H35	119.9
O20—C20—C21	125.24 (17)	C36—C35—H35	120.1
O2—C20—C21	113.45 (15)	C35—C36—C31	119.8 (2)
C26—C21—C22	119.4 (2)	C35—C36—H36	120.5
C26—C21—C20	122.61 (18)	C31—C36—H36	119.7
C22—C21—C20	117.82 (18)	N4—C41—H411	108.1
C23—C22—C21	119.7 (2)	N4—C41—H412	110.2
C23—C22—H22	120.1	H411—C41—H412	110.1
C21—C22—H22	120.2	N4—C41—H413	110.1
C24—C23—C22	120.6 (2)	H411—C41—H413	110.1
C24—C23—H23	119.7	H412—C41—H413	108.4
C22—C23—H23	119.7	C4—N4—C41	122.97 (18)
C23—C24—C25	119.9 (2)	C4—N4—H4	118.4
C23—C24—H24	119.9	C41—N4—H4	118.6
C25—C24—H24	120.2	C20—O2—C2	114.24 (13)
C24—C25—C26	120.0 (2)	C30—O3—C3	116.90 (14)
C24—C25—H25	119.9	C1—O10—H10	109.6 (14)
C26—C25—H25	120.1	H1W—O1W—H2W	108 (3)
C25—C26—C21	120.19 (19)
O1—C1—C2—O2	27.5 (3)	C20—C21—C26—C25	−174.4 (2)
O10—C1—C2—O2	−155.04 (14)	O30—C30—C31—C32	−13.2 (4)
O1—C1—C2—C3	−93.3 (2)	O3—C30—C31—C32	167.8 (2)
O10—C1—C2—C3	84.15 (18)	O30—C30—C31—C36	164.9 (2)
O2—C2—C3—O3	−60.75 (17)	O3—C30—C31—C36	−14.2 (3)
C1—C2—C3—O3	62.21 (18)	C36—C31—C32—C33	1.2 (4)
O2—C2—C3—C4	64.20 (18)	C30—C31—C32—C33	179.3 (2)
C1—C2—C3—C4	−172.85 (15)	C31—C32—C33—C34	−1.6 (5)
O3—C3—C4—O4	177.84 (15)	C32—C33—C34—C35	0.9 (5)
C2—C3—C4—O4	53.8 (2)	C33—C34—C35—C36	0.1 (5)
O3—C3—C4—N4	−4.4 (2)	C34—C35—C36—C31	−0.5 (4)
C2—C3—C4—N4	−128.47 (17)	C32—C31—C36—C35	−0.1 (3)
O20—C20—C21—C26	171.0 (2)	C30—C31—C36—C35	−178.2 (2)
O2—C20—C21—C26	−7.2 (3)	O4—C4—N4—C41	1.8 (3)
O20—C20—C21—C22	−4.8 (3)	C3—C4—N4—C41	−175.78 (18)
O2—C20—C21—C22	176.97 (19)	O20—C20—O2—C2	−4.6 (3)
C26—C21—C22—C23	−1.0 (4)	C21—C20—O2—C2	173.64 (16)
C20—C21—C22—C23	175.0 (2)	C3—C2—O2—C20	−167.38 (14)
C21—C22—C23—C24	−1.0 (4)	C1—C2—O2—C20	70.39 (19)
C22—C23—C24—C25	2.5 (4)	O30—C30—O3—C3	−1.9 (3)
C23—C24—C25—C26	−2.1 (4)	C31—C30—O3—C3	177.14 (15)
C24—C25—C26—C21	0.1 (4)	C2—C3—O3—C30	−118.29 (17)
C22—C21—C26—C25	1.4 (3)	C4—C3—O3—C30	116.47 (17)

(boh3) (R,R)-(-)-O,O'-Dibenzoyltartaric acid mono(N,N-dimethylamide)

Crystal data

C20H19NO7	F(000) = 808
Mr = 385.36	Dx = 1.318 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
a = 8.6699 (6) Å	µ = 0.10 mm^−1
b = 12.0105 (7) Å	T = 120 K
c = 18.657 (1) Å	Prism, colourless
V = 1942.8 (2) Å^3	0.5 × 0.2 × 0.1 mm
Z = 4

Data collection

Kuma KM4CCD κ-geometry diffractometer	2444 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.073
Graphite monochromator	θmax = 28.3°, θmin = 4.1°
ω scans	h = −11→11
19283 measured reflections	k = −8→16
2726 independent reflections	l = −24→24

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.117	Calculated w = 1/[σ^2(Fo^2) + (0.0639P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max < 0.001
2726 reflections	Δρmax = 0.22 e Å^−3
257 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	−0.0724 (3)	−0.1814 (2)	0.29720 (12)	0.0288 (5)
C2	0.0568 (3)	−0.10213 (19)	0.32011 (12)	0.0274 (5)
H2	0.1259	−0.1411	0.3515	0.033*
C3	0.1483 (3)	−0.0578 (2)	0.25687 (13)	0.0275 (5)
H3	0.1911	−0.1189	0.2303	0.033*
C4	0.2787 (3)	0.0195 (2)	0.28122 (13)	0.0294 (5)
O1	−0.1964 (2)	−0.18285 (17)	0.32598 (11)	0.0436 (5)
O10	−0.0271 (2)	−0.24888 (14)	0.24550 (10)	0.0332 (4)
H10	−0.102 (4)	−0.294 (3)	0.2354 (18)	0.056 (10)*
O2	−0.0105 (2)	−0.01127 (13)	0.35842 (8)	0.0325 (4)
O3	0.04257 (18)	0.00241 (13)	0.21205 (8)	0.0274 (4)
O4	0.2550 (2)	0.11963 (14)	0.29196 (10)	0.0377 (4)
N4	0.4159 (2)	−0.02778 (17)	0.29345 (11)	0.0322 (5)
C41	0.5433 (3)	0.0442 (2)	0.31734 (18)	0.0439 (7)
H411	0.5135	0.0781	0.3618	0.053*
H412	0.5640	0.1004	0.2821	0.053*
H413	0.6351	0.0006	0.3239	0.053*
C42	0.4510 (3)	−0.1429 (2)	0.27353 (16)	0.0394 (6)
H421	0.3808	−0.1937	0.2962	0.047*
H422	0.5547	−0.1606	0.2875	0.047*
H423	0.4436	−0.1507	0.2224	0.047*
C20	0.0160 (3)	−0.00687 (19)	0.42985 (12)	0.0280 (5)
O20	0.0952 (3)	−0.07459 (19)	0.45973 (11)	0.0613 (7)
C21	−0.0616 (3)	0.08829 (19)	0.46425 (12)	0.0269 (5)
C22	−0.0595 (3)	0.0944 (2)	0.53897 (14)	0.0366 (6)
H22	−0.0082	0.0376	0.5662	0.044*
C23	−0.1307 (3)	0.1832 (2)	0.57343 (15)	0.0429 (7)
H23	−0.1308	0.1867	0.6248	0.052*
C24	−0.2010 (3)	0.2654 (3)	0.53423 (17)	0.0459 (7)
H24	−0.2496	0.3264	0.5586	0.055*
C25	−0.2028 (3)	0.2605 (2)	0.45977 (16)	0.0447 (7)
H25	−0.2519	0.3187	0.4329	0.054*
C26	−0.1337 (3)	0.1715 (2)	0.42473 (14)	0.0343 (6)
H26	−0.1356	0.1674	0.3733	0.041*
C30	0.1011 (3)	0.0260 (2)	0.14575 (13)	0.0302 (5)
O30	0.2332 (2)	0.00535 (16)	0.13089 (9)	0.0391 (4)
C31	−0.0143 (3)	0.0775 (2)	0.09803 (13)	0.0308 (5)
C32	0.0281 (4)	0.0958 (2)	0.02714 (14)	0.0389 (6)
H32	0.1299	0.0767	0.0111	0.047*
C33	−0.0788 (4)	0.1420 (2)	−0.01993 (15)	0.0480 (8)
H33	−0.0505	0.1549	−0.0690	0.058*
C34	−0.2242 (4)	0.1695 (2)	0.00305 (16)	0.0455 (7)
H34	−0.2970	0.2014	−0.0299	0.055*
C35	−0.2652 (4)	0.1516 (2)	0.07331 (16)	0.0439 (7)
H35	−0.3673	0.1707	0.0891	0.053*
C36	−0.1618 (3)	0.1045 (2)	0.12116 (14)	0.0344 (6)
H36	−0.1905	0.0923	0.1702	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0308 (12)	0.0302 (12)	0.0255 (11)	0.0054 (10)	−0.0003 (10)	0.0060 (10)
C2	0.0307 (12)	0.0271 (12)	0.0246 (11)	0.0093 (10)	−0.0008 (10)	0.0000 (9)
C3	0.0274 (12)	0.0248 (12)	0.0303 (12)	0.0052 (9)	−0.0029 (10)	−0.0020 (9)
C4	0.0289 (12)	0.0300 (12)	0.0294 (12)	0.0024 (10)	−0.0014 (10)	−0.0009 (10)
O1	0.0305 (10)	0.0562 (12)	0.0440 (11)	0.0029 (9)	0.0059 (8)	−0.0019 (9)
O10	0.0327 (10)	0.0290 (9)	0.0379 (10)	−0.0032 (8)	0.0035 (8)	−0.0041 (8)
O2	0.0423 (10)	0.0301 (8)	0.0251 (8)	0.0141 (8)	−0.0012 (7)	−0.0018 (7)
O3	0.0287 (8)	0.0290 (8)	0.0246 (8)	0.0032 (7)	−0.0012 (7)	0.0003 (7)
O4	0.0366 (10)	0.0275 (9)	0.0490 (11)	0.0050 (8)	−0.0106 (9)	−0.0067 (8)
N4	0.0280 (10)	0.0303 (11)	0.0384 (11)	0.0002 (9)	−0.0019 (9)	−0.0021 (9)
C41	0.0351 (14)	0.0371 (15)	0.0596 (18)	−0.0041 (12)	−0.0121 (14)	−0.0011 (13)
C42	0.0292 (13)	0.0351 (14)	0.0538 (17)	0.0077 (11)	−0.0002 (12)	−0.0047 (12)
C20	0.0286 (11)	0.0273 (11)	0.0280 (11)	0.0013 (10)	−0.0054 (10)	−0.0021 (9)
O20	0.0839 (17)	0.0613 (13)	0.0387 (11)	0.0445 (13)	−0.0224 (11)	−0.0144 (10)
C21	0.0243 (11)	0.0280 (11)	0.0285 (12)	−0.0011 (9)	−0.0012 (10)	−0.0035 (9)
C22	0.0394 (14)	0.0376 (14)	0.0328 (13)	0.0065 (12)	−0.0068 (12)	−0.0033 (11)
C23	0.0439 (15)	0.0505 (17)	0.0343 (14)	0.0093 (13)	−0.0052 (12)	−0.0117 (12)
C24	0.0428 (15)	0.0442 (16)	0.0506 (17)	0.0135 (13)	−0.0040 (14)	−0.0175 (14)
C25	0.0498 (17)	0.0365 (15)	0.0480 (17)	0.0157 (13)	−0.0001 (14)	−0.0006 (13)
C26	0.0365 (13)	0.0312 (13)	0.0352 (13)	0.0061 (11)	0.0027 (11)	−0.0005 (10)
C30	0.0333 (13)	0.0262 (11)	0.0310 (12)	−0.0023 (10)	0.0026 (11)	−0.0032 (10)
O30	0.0338 (9)	0.0470 (10)	0.0365 (10)	0.0014 (8)	0.0052 (8)	−0.0001 (8)
C31	0.0384 (13)	0.0247 (11)	0.0293 (12)	−0.0070 (10)	−0.0033 (11)	−0.0018 (9)
C32	0.0499 (16)	0.0357 (13)	0.0311 (12)	−0.0058 (13)	0.0010 (12)	0.0014 (11)
C33	0.069 (2)	0.0436 (16)	0.0315 (14)	−0.0099 (15)	−0.0079 (14)	0.0068 (12)
C34	0.062 (2)	0.0333 (14)	0.0414 (15)	−0.0038 (14)	−0.0211 (15)	0.0016 (12)
C35	0.0491 (16)	0.0392 (14)	0.0433 (16)	0.0034 (13)	−0.0113 (14)	−0.0008 (12)
C36	0.0413 (14)	0.0325 (13)	0.0293 (12)	0.0025 (11)	−0.0041 (11)	−0.0010 (11)

Geometric parameters (Å, º)

C1—O1	1.201 (3)	C21—C26	1.390 (3)
C1—O10	1.320 (3)	C21—C22	1.396 (3)
C1—C2	1.531 (3)	C22—C23	1.390 (4)
C2—O2	1.429 (3)	C22—H22	0.9599
C2—C3	1.518 (3)	C23—C24	1.372 (4)
C2—H2	0.9600	C23—H23	0.9601
C3—O3	1.436 (3)	C24—C25	1.390 (4)
C3—C4	1.531 (3)	C24—H24	0.9600
C3—H3	0.9600	C25—C26	1.389 (4)
C4—O4	1.237 (3)	C25—H25	0.9600
C4—N4	1.337 (3)	C26—H26	0.9600
O10—H10	0.87 (4)	C30—O30	1.205 (3)
O2—C20	1.353 (3)	C30—C31	1.475 (4)
O3—C30	1.366 (3)	C31—C36	1.388 (4)
N4—C42	1.464 (3)	C31—C32	1.390 (3)
N4—C41	1.472 (3)	C32—C33	1.392 (4)
C41—H411	0.9599	C32—H32	0.9600
C41—H412	0.9599	C33—C34	1.372 (5)
C41—H413	0.9600	C33—H33	0.9601
C42—H421	0.9600	C34—C35	1.375 (4)
C42—H422	0.9600	C34—H34	0.9600
C42—H423	0.9600	C35—C36	1.386 (4)
C20—O20	1.201 (3)	C35—H35	0.9600
C20—C21	1.474 (3)	C36—H36	0.9600
O1—C1—O10	125.7 (2)	C26—C21—C22	119.9 (2)
O1—C1—C2	122.6 (2)	C26—C21—C20	122.1 (2)
O10—C1—C2	111.6 (2)	C22—C21—C20	118.0 (2)
O2—C2—C3	109.51 (19)	C23—C22—C21	119.8 (2)
O2—C2—C1	108.40 (19)	C23—C22—H22	120.4
C3—C2—C1	112.57 (19)	C21—C22—H22	119.8
O2—C2—H2	108.8	C24—C23—C22	120.2 (3)
C3—C2—H2	108.6	C24—C23—H23	120.0
C1—C2—H2	108.9	C22—C23—H23	119.8
O3—C3—C2	107.19 (18)	C23—C24—C25	120.5 (3)
O3—C3—C4	109.84 (18)	C23—C24—H24	119.5
C2—C3—C4	111.59 (19)	C25—C24—H24	120.1
O3—C3—H3	109.3	C26—C25—C24	119.9 (3)
C2—C3—H3	109.5	C26—C25—H25	120.4
C4—C3—H3	109.3	C24—C25—H25	119.7
O4—C4—N4	122.2 (2)	C25—C26—C21	119.8 (2)
O4—C4—C3	121.0 (2)	C25—C26—H26	120.2
N4—C4—C3	116.8 (2)	C21—C26—H26	120.0
C1—O10—H10	109 (2)	O30—C30—O3	121.2 (2)
C20—O2—C2	116.93 (18)	O30—C30—C31	126.3 (2)
C30—O3—C3	113.23 (18)	O3—C30—C31	112.4 (2)
C4—N4—C42	122.8 (2)	C36—C31—C32	120.1 (2)
C4—N4—C41	118.0 (2)	C36—C31—C30	122.4 (2)
C42—N4—C41	118.4 (2)	C32—C31—C30	117.5 (2)
N4—C41—H411	108.0	C31—C32—C33	119.2 (3)
N4—C41—H412	110.2	C31—C32—H32	120.2
H411—C41—H412	110.1	C33—C32—H32	120.6
N4—C41—H413	109.9	C34—C33—C32	120.7 (3)
H411—C41—H413	110.1	C34—C33—H33	119.6
H412—C41—H413	108.4	C32—C33—H33	119.7
N4—C42—H421	110.9	C33—C34—C35	119.9 (3)
N4—C42—H422	109.6	C33—C34—H34	120.0
H421—C42—H422	109.5	C35—C34—H34	120.1
N4—C42—H423	109.3	C34—C35—C36	120.7 (3)
H421—C42—H423	109.5	C34—C35—H35	119.5
H422—C42—H423	108.1	C36—C35—H35	119.8
O20—C20—O2	121.8 (2)	C35—C36—C31	119.4 (2)
O20—C20—C21	125.7 (2)	C35—C36—H36	120.6
O2—C20—C21	112.43 (19)	C31—C36—H36	119.9
O1—C1—C2—O2	−20.7 (3)	O20—C20—C21—C22	−8.1 (4)
O10—C1—C2—O2	162.20 (18)	O2—C20—C21—C22	172.1 (2)
O1—C1—C2—C3	−142.0 (2)	C26—C21—C22—C23	0.5 (4)
O10—C1—C2—C3	40.9 (3)	C20—C21—C22—C23	179.6 (2)
O2—C2—C3—O3	−59.9 (2)	C21—C22—C23—C24	−0.9 (4)
C1—C2—C3—O3	60.8 (2)	C22—C23—C24—C25	0.4 (4)
O2—C2—C3—C4	60.4 (2)	C23—C24—C25—C26	0.4 (5)
C1—C2—C3—C4	−178.91 (18)	C24—C25—C26—C21	−0.7 (4)
O3—C3—C4—O4	33.1 (3)	C22—C21—C26—C25	0.3 (4)
C2—C3—C4—O4	−85.6 (3)	C20—C21—C26—C25	−178.8 (2)
O3—C3—C4—N4	−150.1 (2)	C3—O3—C30—O30	−6.0 (3)
C2—C3—C4—N4	91.2 (3)	C3—O3—C30—C31	174.16 (18)
C3—C2—O2—C20	−127.5 (2)	O30—C30—C31—C36	−175.9 (2)
C1—C2—O2—C20	109.4 (2)	O3—C30—C31—C36	3.9 (3)
C2—C3—O3—C30	−166.44 (18)	O30—C30—C31—C32	5.9 (4)
C4—C3—O3—C30	72.2 (2)	O3—C30—C31—C32	−174.3 (2)
O4—C4—N4—C42	−172.9 (2)	C36—C31—C32—C33	0.4 (4)
C3—C4—N4—C42	10.3 (3)	C30—C31—C32—C33	178.6 (2)
O4—C4—N4—C41	−2.8 (4)	C31—C32—C33—C34	0.1 (4)
C3—C4—N4—C41	−179.6 (2)	C32—C33—C34—C35	0.2 (4)
C2—O2—C20—O20	1.6 (3)	C33—C34—C35—C36	−1.0 (4)
C2—O2—C20—C21	−178.59 (19)	C34—C35—C36—C31	1.4 (4)
O20—C20—C21—C26	171.0 (3)	C32—C31—C36—C35	−1.1 (4)
O2—C20—C21—C26	−8.8 (3)	C30—C31—C36—C35	−179.2 (2)

(bn13) (R,R)-(-)-O,O'-Dibenzoyltartaric acid N,N-dimethyldiamide

Crystal data

C20H20N2O6	F(000) = 808
Mr = 384.38	Dx = 1.355 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
a = 8.9153 (6) Å	µ = 0.10 mm^−1
b = 11.758 (1) Å	T = 150 K
c = 17.976 (1) Å	Plate, colourless
V = 1884.4 (2) Å^3	0.40 × 0.20 × 0.05 mm
Z = 4

Data collection

Kuma KM4CCD κ-geometry diffractometer	1697 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.069
Graphite monochromator	θmax = 28.3°, θmin = 4.1°
ω scans	h = −8→11
12108 measured reflections	k = −15→15
2545 independent reflections	l = −22→23

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.099	Calculated w = 1/[σ^2(Fo^2) + (0.0471P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max < 0.001
2545 reflections	Δρmax = 0.17 e Å^−3
253 parameters	Δρmin = −0.23 e Å^−3
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1554 (3)	−0.9495 (2)	−1.00258 (16)	0.0268 (6)
C2	−0.0044 (3)	−0.9472 (2)	−1.03195 (16)	0.0265 (6)
H2	−0.0174	−1.0117	−1.0640	0.032*
C3	−0.1140 (3)	−0.9592 (2)	−0.96750 (16)	0.0246 (6)
H3	−0.0878	−1.0253	−0.9390	0.029*
C4	−0.2770 (3)	−0.9709 (2)	−0.99273 (17)	0.0264 (6)
C20	−0.1138 (3)	−0.8643 (3)	−1.13987 (16)	0.0288 (7)
C21	−0.1185 (3)	−0.7624 (3)	−1.18797 (17)	0.0279 (7)
C22	−0.1850 (3)	−0.7741 (3)	−1.25814 (18)	0.0384 (8)
H22	−0.2232	−0.8465	−1.2738	0.046*
C23	−0.1940 (4)	−0.6809 (4)	−1.3047 (2)	0.0481 (9)
H23	−0.2403	−0.6884	−1.3526	0.058*
C24	−0.1384 (4)	−0.5767 (3)	−1.2828 (2)	0.0440 (9)
H24	−0.1484	−0.5117	−1.3147	0.053*
C25	−0.0694 (3)	−0.5659 (3)	−1.21449 (19)	0.0399 (9)
H25	−0.0280	−0.4942	−1.1994	0.048*
C26	−0.0590 (3)	−0.6583 (3)	−1.16705 (18)	0.0319 (8)
H26	−0.0093	−0.6512	−1.1199	0.038*
C30	−0.1610 (3)	−0.8738 (3)	−0.85191 (16)	0.0268 (7)
C31	−0.1374 (3)	−0.7731 (3)	−0.80403 (16)	0.0278 (7)
C32	−0.2147 (3)	−0.7702 (3)	−0.73644 (17)	0.0349 (8)
H32	−0.2795	−0.8318	−0.7227	0.042*
C33	−0.1974 (4)	−0.6777 (3)	−0.68925 (18)	0.0404 (8)
H33	−0.2517	−0.6738	−0.6432	0.048*
C34	−0.1027 (3)	−0.5903 (3)	−0.70909 (19)	0.0397 (8)
H34	−0.0900	−0.5267	−0.6762	0.048*
C35	−0.0238 (4)	−0.5931 (3)	−0.77557 (18)	0.0385 (8)
H35	0.0429	−0.5321	−0.7884	0.046*
C36	−0.0422 (3)	−0.6844 (3)	−0.82361 (17)	0.0334 (8)
H36	0.0109	−0.6867	−0.8700	0.040*
C41	−0.4694 (3)	−1.0877 (3)	−1.0485 (2)	0.0455 (9)
H411	−0.5378	−1.1169	−1.0121	0.055*
H412	−0.4628	−1.1392	−1.0898	0.055*
H413	−0.5043	−1.0157	−1.0667	0.055*
C42	−0.2303 (4)	−1.1767 (3)	−1.0076 (2)	0.0503 (10)
H421	−0.1823	−1.1784	−0.9599	0.060*
H422	−0.1560	−1.1763	−1.0462	0.060*
H423	−0.2912	−1.2433	−1.0137	0.060*
O1	0.1997 (2)	−1.03923 (17)	−0.97496 (13)	0.0380 (5)
O2	−0.0317 (2)	−0.84678 (16)	−1.07580 (11)	0.0268 (5)
O3	−0.0973 (2)	−0.86096 (17)	−0.92126 (11)	0.0277 (5)
O4	−0.3591 (2)	−0.88621 (16)	−0.99564 (11)	0.0329 (5)
O20	−0.1718 (2)	−0.95470 (19)	−1.15341 (12)	0.0393 (6)
O30	−0.2256 (2)	−0.95943 (18)	−0.83470 (12)	0.0351 (5)
N1	0.2387 (3)	−0.85587 (19)	−1.00891 (14)	0.0326 (6)
H11	0.3334	−0.8545	−0.9919	0.039*
H12	0.1991	−0.7936	−1.0303	0.039*
N4	−0.3220 (3)	−1.07442 (19)	−1.01389 (14)	0.0302 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0284 (16)	0.0247 (14)	0.0273 (15)	0.0021 (12)	0.0047 (14)	−0.0012 (15)
C2	0.0313 (16)	0.0219 (15)	0.0264 (15)	−0.0011 (13)	−0.0011 (14)	−0.0026 (13)
C3	0.0324 (15)	0.0178 (13)	0.0234 (14)	0.0000 (12)	0.0031 (13)	−0.0033 (13)
C4	0.0274 (15)	0.0233 (14)	0.0285 (16)	−0.0023 (12)	0.0059 (13)	−0.0028 (14)
C20	0.0248 (15)	0.0376 (18)	0.0241 (16)	0.0020 (14)	0.0031 (13)	−0.0049 (15)
C21	0.0233 (15)	0.0343 (18)	0.0260 (17)	0.0026 (13)	0.0016 (13)	−0.0014 (14)
C22	0.0386 (19)	0.046 (2)	0.0309 (18)	−0.0013 (17)	−0.0052 (15)	−0.0022 (17)
C23	0.047 (2)	0.065 (3)	0.0314 (19)	0.005 (2)	−0.0083 (16)	0.0066 (19)
C24	0.0343 (18)	0.057 (2)	0.041 (2)	0.0047 (17)	0.0008 (16)	0.0189 (19)
C25	0.0315 (17)	0.044 (2)	0.045 (2)	0.0012 (15)	−0.0015 (16)	0.0088 (18)
C26	0.0279 (16)	0.0374 (19)	0.0303 (17)	0.0019 (14)	−0.0006 (13)	0.0011 (15)
C30	0.0254 (15)	0.0294 (17)	0.0256 (16)	0.0067 (13)	0.0036 (13)	0.0019 (14)
C31	0.0253 (15)	0.0326 (16)	0.0255 (16)	0.0036 (13)	−0.0028 (13)	0.0005 (14)
C32	0.0363 (18)	0.0395 (18)	0.0289 (17)	0.0027 (15)	0.0043 (14)	0.0007 (15)
C33	0.0453 (19)	0.050 (2)	0.0263 (18)	0.0050 (18)	0.0032 (15)	−0.0072 (16)
C34	0.0395 (18)	0.042 (2)	0.037 (2)	0.0023 (16)	−0.0052 (16)	−0.0119 (17)
C35	0.0353 (18)	0.041 (2)	0.039 (2)	−0.0061 (16)	−0.0002 (16)	−0.0096 (16)
C36	0.0317 (16)	0.0403 (19)	0.0281 (17)	−0.0025 (14)	0.0024 (14)	−0.0052 (15)
C41	0.0283 (17)	0.0390 (19)	0.069 (3)	−0.0073 (15)	0.0002 (17)	−0.0133 (19)
C42	0.054 (2)	0.0245 (15)	0.073 (3)	0.0021 (15)	−0.008 (2)	−0.0069 (19)
O1	0.0358 (12)	0.0282 (11)	0.0501 (14)	0.0049 (10)	0.0026 (11)	0.0116 (11)
O2	0.0316 (10)	0.0246 (10)	0.0242 (11)	−0.0001 (9)	−0.0010 (9)	0.0033 (9)
O3	0.0327 (11)	0.0253 (11)	0.0250 (11)	−0.0006 (9)	0.0042 (9)	−0.0038 (10)
O4	0.0331 (11)	0.0271 (10)	0.0385 (12)	0.0030 (9)	0.0022 (10)	−0.0009 (11)
O20	0.0439 (13)	0.0342 (12)	0.0399 (13)	−0.0068 (11)	−0.0061 (11)	−0.0051 (11)
O30	0.0407 (12)	0.0308 (12)	0.0338 (12)	−0.0007 (10)	0.0078 (10)	0.0050 (11)
N1	0.0286 (13)	0.0297 (13)	0.0395 (16)	−0.0024 (11)	−0.0072 (12)	0.0071 (13)
N4	0.0284 (13)	0.0227 (12)	0.0394 (16)	−0.0020 (10)	0.0044 (12)	−0.0040 (11)

Geometric parameters (Å, º)

C1—O1	1.232 (3)	C30—O30	1.201 (3)
C1—N1	1.332 (3)	C30—O3	1.378 (3)
C1—C2	1.519 (4)	C30—C31	1.479 (4)
C2—O2	1.441 (3)	C31—C36	1.390 (4)
C2—C3	1.522 (4)	C31—C32	1.397 (4)
C2—H2	0.9594	C32—C33	1.388 (4)
C3—O3	1.431 (3)	C32—H32	0.9593
C3—C4	1.528 (4)	C33—C34	1.377 (5)
C3—H3	0.9594	C33—H33	0.9592
C4—O4	1.237 (3)	C34—C35	1.387 (4)
C4—N4	1.337 (3)	C34—H34	0.9595
C20—O20	1.207 (4)	C35—C36	1.388 (4)
C20—O2	1.380 (3)	C35—H35	0.9593
C20—C21	1.477 (4)	C36—H36	0.9594
C21—C26	1.386 (4)	C41—N4	1.462 (4)
C21—C22	1.400 (4)	C41—H411	0.9592
C22—C23	1.381 (5)	C41—H412	0.9595
C22—H22	0.9594	C41—H413	0.9594
C23—C24	1.378 (5)	C42—N4	1.459 (4)
C23—H23	0.9593	C42—H421	0.9592
C24—C25	1.380 (5)	C42—H422	0.9592
C24—H24	0.9594	C42—H423	0.9593
C25—C26	1.385 (4)	N1—H11	0.8991
C25—H25	0.9594	N1—H12	0.8994
C26—H26	0.9594
O1—C1—N1	124.3 (3)	O30—C30—C31	126.1 (3)
O1—C1—C2	117.1 (2)	O3—C30—C31	112.3 (2)
N1—C1—C2	118.6 (2)	C36—C31—C32	120.2 (3)
O2—C2—C1	111.3 (2)	C36—C31—C30	122.7 (3)
O2—C2—C3	112.6 (2)	C32—C31—C30	117.1 (3)
C1—C2—C3	109.6 (2)	C33—C32—C31	119.7 (3)
O2—C2—H2	107.4	C33—C32—H32	120.1
C1—C2—H2	108.0	C31—C32—H32	120.2
C3—C2—H2	107.8	C34—C33—C32	119.6 (3)
O3—C3—C2	107.5 (2)	C34—C33—H33	119.8
O3—C3—C4	110.1 (2)	C32—C33—H33	120.6
C2—C3—C4	113.1 (2)	C33—C34—C35	121.1 (3)
O3—C3—H3	108.5	C33—C34—H34	119.6
C2—C3—H3	109.0	C35—C34—H34	119.3
C4—C3—H3	108.5	C34—C35—C36	119.6 (3)
O4—C4—N4	122.9 (3)	C34—C35—H35	120.3
O4—C4—C3	120.2 (2)	C36—C35—H35	120.1
N4—C4—C3	116.8 (2)	C35—C36—C31	119.7 (3)
O20—C20—O2	121.8 (3)	C35—C36—H36	120.3
O20—C20—C21	125.7 (3)	C31—C36—H36	120.0
O2—C20—C21	112.5 (3)	N4—C41—H411	108.6
C26—C21—C22	119.5 (3)	N4—C41—H412	110.0
C26—C21—C20	123.1 (3)	H411—C41—H412	110.0
C22—C21—C20	117.4 (3)	N4—C41—H413	110.0
C23—C22—C21	119.5 (3)	H411—C41—H413	110.0
C23—C22—H22	120.4	H412—C41—H413	108.3
C21—C22—H22	120.0	N4—C42—H421	109.6
C24—C23—C22	120.7 (3)	N4—C42—H422	109.1
C24—C23—H23	119.5	H421—C42—H422	109.8
C22—C23—H23	119.8	N4—C42—H423	110.3
C23—C24—C25	119.8 (3)	H421—C42—H423	109.8
C23—C24—H24	120.3	H422—C42—H423	108.2
C25—C24—H24	119.9	C20—O2—C2	115.1 (2)
C24—C25—C26	120.4 (3)	C30—O3—C3	113.2 (2)
C24—C25—H25	120.3	C1—N1—H11	120.6
C26—C25—H25	119.3	C1—N1—H12	119.4
C25—C26—C21	120.0 (3)	H11—N1—H12	120.0
C25—C26—H26	120.4	C4—N4—C42	124.1 (2)
C21—C26—H26	119.6	C4—N4—C41	119.2 (2)
O30—C30—O3	121.5 (3)	C42—N4—C41	116.6 (2)
O1—C1—C2—O2	−168.2 (2)	O30—C30—C31—C36	169.8 (3)
N1—C1—C2—O2	11.0 (4)	O3—C30—C31—C36	−9.2 (4)
O1—C1—C2—C3	66.6 (3)	O30—C30—C31—C32	−9.6 (4)
N1—C1—C2—C3	−114.2 (3)	O3—C30—C31—C32	171.3 (2)
O2—C2—C3—O3	−59.9 (3)	C36—C31—C32—C33	0.8 (4)
C1—C2—C3—O3	64.5 (3)	C30—C31—C32—C33	−179.8 (3)
O2—C2—C3—C4	61.8 (3)	C31—C32—C33—C34	−0.8 (5)
C1—C2—C3—C4	−173.7 (2)	C32—C33—C34—C35	−0.1 (5)
O3—C3—C4—O4	24.8 (4)	C33—C34—C35—C36	1.1 (5)
C2—C3—C4—O4	−95.5 (3)	C34—C35—C36—C31	−1.1 (5)
O3—C3—C4—N4	−157.9 (2)	C32—C31—C36—C35	0.2 (5)
C2—C3—C4—N4	81.8 (3)	C30—C31—C36—C35	−179.2 (3)
O20—C20—C21—C26	175.2 (3)	O20—C20—O2—C2	7.8 (4)
O2—C20—C21—C26	−5.9 (4)	C21—C20—O2—C2	−171.3 (2)
O20—C20—C21—C22	−5.7 (4)	C1—C2—O2—C20	138.4 (2)
O2—C20—C21—C22	173.3 (2)	C3—C2—O2—C20	−98.1 (3)
C26—C21—C22—C23	−1.8 (5)	O30—C30—O3—C3	−1.3 (4)
C20—C21—C22—C23	179.1 (3)	C31—C30—O3—C3	177.8 (2)
C21—C22—C23—C24	0.0 (5)	C2—C3—O3—C30	−164.5 (2)
C22—C23—C24—C25	1.7 (5)	C4—C3—O3—C30	71.8 (3)
C23—C24—C25—C26	−1.6 (5)	O4—C4—N4—C42	−176.8 (3)
C24—C25—C26—C21	−0.2 (5)	C3—C4—N4—C42	6.0 (5)
C22—C21—C26—C25	1.9 (4)	O4—C4—N4—C41	5.9 (5)
C20—C21—C26—C25	−179.0 (3)	C3—C4—N4—C41	−171.3 (2)

(bn23) (R,R)-(-)-O,O'-Dibenzoyltartaric acid N,N,N'-trimethyldiamide

Crystal data

C21H22N2O6	F(000) = 420
Mr = 398.41	Dx = 1.284 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 8.901 (1) Å	Cell parameters from 30 reflections
b = 11.272 (1) Å	θ = 8.4–11.3°
c = 10.414 (1) Å	µ = 0.10 mm^−1
β = 99.47 (1)°	T = 293 K
V = 1030.62 (18) Å^3	Prism, colourless
Z = 2	0.6 × 0.3 × 0.3 mm

Data collection

KM-4 four circle diffractometer	Rint = 0.016
Radiation source: fine-focus sealed tube	θmax = 26.1°, θmin = 2.0°
Graphite monochromator	h = −11→10
Θ–2Θ scans	k = −13→13
4029 measured reflections	l = 0→12
2127 independent reflections	2 standard reflections every 100 reflections
1752 reflections with I > 2σ(I)	intensity decay: 1.9%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.084	Calculated w = 1/[σ^2(Fo^2) + (0.0444P)^2 + 0.128P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
2127 reflections	Δρmax = 0.14 e Å^−3
262 parameters	Δρmin = −0.13 e Å^−3
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	−0.1058 (2)	0.2708 (2)	0.6381 (2)	0.0370 (5)
C2	0.0669 (2)	0.25491 (19)	0.6591 (2)	0.0364 (5)
H2	0.0962	0.2045	0.7334	0.050*
C3	0.1145 (2)	0.19547 (19)	0.5419 (2)	0.0363 (5)
H3	0.0613	0.1216	0.5244	0.050*
C4	0.2872 (3)	0.1737 (2)	0.5606 (2)	0.0420 (5)
C11	−0.3207 (3)	0.4017 (3)	0.6478 (3)	0.0571 (7)
H111	−0.3388	0.4846	0.6600	0.100*
H112	−0.3593	0.3565	0.7134	0.100*
H113	−0.3734	0.3769	0.5643	0.100*
C20	0.2511 (3)	0.3733 (2)	0.7927 (2)	0.0476 (6)
C21	0.3356 (3)	0.4873 (2)	0.7996 (3)	0.0474 (6)
C22	0.4292 (4)	0.5129 (3)	0.9159 (3)	0.0775 (10)
H22	0.4324	0.4608	0.9892	0.070*
C23	0.5158 (5)	0.6155 (4)	0.9255 (4)	0.0944 (13)
H23	0.5795	0.6348	1.0064	0.100*
C24	0.5114 (4)	0.6891 (3)	0.8217 (4)	0.0872 (11)
H24	0.5739	0.7590	0.8288	0.100*
C25	0.4183 (3)	0.6637 (3)	0.7059 (3)	0.0668 (8)
H25	0.4158	0.7162	0.6329	0.100*
C26	0.3292 (3)	0.5622 (2)	0.6949 (3)	0.0504 (6)
H26	0.2636	0.5441	0.6146	0.070*
C30	0.0511 (3)	0.2247 (2)	0.3156 (2)	0.0415 (5)
C31	0.0220 (3)	0.3132 (2)	0.2103 (2)	0.0430 (5)
C32	−0.0820 (4)	0.2850 (3)	0.1003 (2)	0.0616 (7)
H32	−0.1323	0.2094	0.0941	0.070*
C33	−0.1131 (5)	0.3667 (4)	−0.0001 (3)	0.0844 (11)
H33	−0.1869	0.3488	−0.0756	0.100*
C34	−0.0362 (5)	0.4733 (4)	0.0086 (3)	0.0857 (12)
H34	−0.0574	0.5298	−0.0610	0.100*
C35	0.0676 (4)	0.5015 (3)	0.1170 (3)	0.0732 (9)
H35	0.1221	0.5753	0.1208	0.100*
C36	0.0959 (3)	0.4221 (2)	0.2194 (3)	0.0528 (6)
H36	0.1661	0.4421	0.2965	0.070*
C41	0.5065 (3)	0.0604 (3)	0.6616 (3)	0.0694 (8)
H411	0.5300	−0.0064	0.6112	0.140*
H412	0.5381	0.0450	0.7527	0.140*
H413	0.5594	0.1296	0.6388	0.140*
C42	0.2500 (3)	−0.0082 (2)	0.6873 (3)	0.0602 (7)
H421	0.3064	−0.0809	0.7015	0.140*
H422	0.1566	−0.0217	0.6285	0.140*
H423	0.2254	0.0202	0.7682	0.140*
N1	−0.1586 (2)	0.37839 (19)	0.6559 (2)	0.0439 (5)
H1	−0.0923	0.4387	0.6736	0.050*
N4	0.3417 (2)	0.07952 (19)	0.6326 (2)	0.0478 (5)
O1	−0.1847 (2)	0.18349 (17)	0.6098 (2)	0.0628 (5)
O2	0.14441 (16)	0.36662 (14)	0.68353 (14)	0.0380 (3)
O3	0.07368 (18)	0.27469 (14)	0.43422 (14)	0.0419 (4)
O4	0.3675 (2)	0.24239 (18)	0.5121 (2)	0.0657 (6)
O20	0.2724 (3)	0.2960 (2)	0.8700 (2)	0.0960 (10)
O30	0.0524 (3)	0.11960 (17)	0.29874 (19)	0.0626 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0351 (11)	0.0349 (11)	0.0409 (11)	−0.0020 (10)	0.0057 (9)	0.0019 (10)
C2	0.0360 (11)	0.0287 (11)	0.0430 (11)	−0.0033 (9)	0.0020 (9)	0.0044 (9)
C3	0.0371 (11)	0.0290 (10)	0.0416 (11)	−0.0008 (9)	0.0033 (9)	0.0034 (9)
C4	0.0383 (11)	0.0379 (12)	0.0506 (12)	−0.0024 (10)	0.0099 (10)	0.0002 (11)
C11	0.0430 (14)	0.0563 (17)	0.0730 (17)	0.0094 (12)	0.0121 (12)	0.0024 (14)
C20	0.0477 (12)	0.0441 (13)	0.0450 (13)	0.0010 (11)	−0.0103 (10)	0.0006 (12)
C21	0.0407 (12)	0.0443 (13)	0.0535 (14)	−0.0008 (11)	−0.0029 (10)	−0.0075 (12)
C22	0.084 (2)	0.068 (2)	0.069 (2)	−0.0161 (18)	−0.0203 (17)	−0.0052 (17)
C23	0.094 (3)	0.076 (2)	0.098 (3)	−0.029 (2)	−0.029 (2)	−0.021 (2)
C24	0.074 (2)	0.058 (2)	0.126 (3)	−0.0261 (18)	0.009 (2)	−0.029 (2)
C25	0.0662 (18)	0.0462 (15)	0.093 (2)	−0.0094 (14)	0.0265 (16)	−0.0058 (16)
C26	0.0434 (12)	0.0446 (14)	0.0637 (16)	−0.0005 (11)	0.0099 (11)	−0.0055 (13)
C30	0.0439 (12)	0.0360 (12)	0.0446 (13)	0.0036 (10)	0.0067 (10)	−0.0036 (10)
C31	0.0470 (13)	0.0426 (13)	0.0408 (12)	0.0078 (10)	0.0111 (10)	0.0005 (10)
C32	0.085 (2)	0.0562 (17)	0.0413 (13)	0.0002 (15)	0.0050 (13)	−0.0037 (13)
C33	0.119 (3)	0.088 (2)	0.0416 (15)	0.006 (2)	−0.0020 (16)	0.0090 (17)
C34	0.128 (3)	0.077 (2)	0.0539 (18)	0.013 (2)	0.022 (2)	0.0260 (18)
C35	0.097 (2)	0.0613 (18)	0.067 (2)	−0.0040 (18)	0.0308 (18)	0.0196 (16)
C36	0.0569 (15)	0.0475 (14)	0.0566 (15)	−0.0006 (12)	0.0168 (12)	0.0048 (13)
C41	0.0381 (13)	0.078 (2)	0.090 (2)	0.0056 (14)	0.0043 (13)	0.0133 (18)
C42	0.0502 (15)	0.0467 (15)	0.085 (2)	0.0062 (12)	0.0149 (14)	0.0253 (15)
N1	0.0367 (10)	0.0387 (10)	0.0557 (11)	0.0015 (8)	0.0061 (8)	−0.0021 (9)
N4	0.0336 (10)	0.0447 (11)	0.0648 (13)	0.0032 (9)	0.0074 (9)	0.0111 (10)
O1	0.0403 (9)	0.0404 (10)	0.1072 (16)	−0.0084 (8)	0.0101 (9)	−0.0078 (11)
O2	0.0357 (7)	0.0346 (8)	0.0404 (8)	−0.0050 (6)	−0.0031 (6)	0.0016 (7)
O3	0.0544 (9)	0.0313 (8)	0.0388 (8)	0.0050 (7)	0.0040 (7)	0.0014 (7)
O4	0.0487 (10)	0.0594 (12)	0.0933 (14)	−0.0038 (9)	0.0247 (10)	0.0235 (11)
O20	0.120 (2)	0.0638 (15)	0.0810 (15)	−0.0290 (14)	−0.0531 (15)	0.0286 (13)
O30	0.0960 (15)	0.0338 (9)	0.0554 (11)	0.0070 (9)	0.0052 (10)	−0.0041 (8)

Geometric parameters (Å, º)

C1—O1	1.217 (3)	C25—C26	1.386 (4)
C1—N1	1.325 (3)	C25—H25	0.9600
C1—C2	1.527 (3)	C26—H26	0.9600
C2—O2	1.438 (3)	C30—O30	1.198 (3)
C2—C3	1.513 (3)	C30—O3	1.342 (3)
C2—H2	0.9600	C30—C31	1.474 (3)
C3—O3	1.433 (2)	C31—C32	1.386 (4)
C3—C4	1.537 (3)	C31—C36	1.388 (4)
C3—H3	0.9599	C32—C33	1.387 (4)
C4—O4	1.218 (3)	C32—H32	0.9600
C4—N4	1.344 (3)	C33—C34	1.378 (6)
C11—N1	1.455 (3)	C33—H33	0.9600
C11—H111	0.9600	C34—C35	1.374 (6)
C11—H112	0.9600	C34—H34	0.9600
C11—H113	0.9600	C35—C36	1.383 (4)
C20—O20	1.180 (3)	C35—H35	0.9600
C20—O2	1.358 (3)	C36—H36	0.9600
C20—C21	1.485 (4)	C41—N4	1.464 (3)
C21—C26	1.373 (4)	C41—H411	0.9600
C21—C22	1.383 (4)	C41—H412	0.9600
C22—C23	1.384 (5)	C41—H413	0.9600
C22—H22	0.9600	C42—N4	1.456 (3)
C23—C24	1.358 (6)	C42—H421	0.9600
C23—H23	0.9600	C42—H422	0.9600
C24—C25	1.377 (5)	C42—H423	0.9600
C24—H24	0.9600	N1—H1	0.9000
O1—C1—N1	124.8 (2)	C21—C26—H26	120.0
O1—C1—C2	117.9 (2)	C25—C26—H26	120.4
N1—C1—C2	117.34 (19)	O30—C30—O3	123.1 (2)
O2—C2—C3	109.89 (17)	O30—C30—C31	124.4 (2)
O2—C2—C1	111.42 (17)	O3—C30—C31	112.5 (2)
C3—C2—C1	110.19 (17)	C32—C31—C36	120.3 (2)
O2—C2—H2	108.4	C32—C31—C30	118.2 (2)
C3—C2—H2	108.2	C36—C31—C30	121.6 (2)
C1—C2—H2	108.6	C31—C32—C33	119.6 (3)
O3—C3—C2	106.68 (16)	C31—C32—H32	120.0
O3—C3—C4	108.51 (17)	C33—C32—H32	120.4
C2—C3—C4	112.07 (17)	C34—C33—C32	119.6 (3)
O3—C3—H3	109.7	C34—C33—H33	120.2
C2—C3—H3	110.0	C32—C33—H33	120.2
C4—C3—H3	109.7	C35—C34—C33	121.0 (3)
O4—C4—N4	123.5 (2)	C35—C34—H34	119.3
O4—C4—C3	119.3 (2)	C33—C34—H34	119.7
N4—C4—C3	117.3 (2)	C34—C35—C36	119.8 (3)
N1—C11—H111	110.7	C34—C35—H35	120.1
N1—C11—H112	109.3	C36—C35—H35	120.2
H111—C11—H112	109.6	C35—C36—C31	119.7 (3)
N1—C11—H113	109.4	C35—C36—H36	120.2
H111—C11—H113	109.6	C31—C36—H36	120.1
H112—C11—H113	108.1	N4—C41—H411	107.7
O20—C20—O2	122.8 (2)	N4—C41—H412	110.5
O20—C20—C21	125.6 (2)	H411—C41—H412	110.1
O2—C20—C21	111.5 (2)	N4—C41—H413	110.2
C26—C21—C22	120.5 (3)	H411—C41—H413	110.1
C26—C21—C20	122.7 (2)	H412—C41—H413	108.4
C22—C21—C20	116.8 (3)	N4—C42—H421	109.1
C21—C22—C23	119.1 (3)	N4—C42—H422	109.9
C21—C22—H22	120.2	H421—C42—H422	109.8
C23—C22—H22	120.7	N4—C42—H423	109.9
C24—C23—C22	120.7 (3)	H421—C42—H423	109.8
C24—C23—H23	119.7	H422—C42—H423	108.3
C22—C23—H23	119.6	C1—N1—C11	121.9 (2)
C23—C24—C25	120.3 (3)	C1—N1—H1	119.0
C23—C24—H24	120.0	C11—N1—H1	119.1
C25—C24—H24	119.7	C4—N4—C42	125.5 (2)
C24—C25—C26	119.9 (3)	C4—N4—C41	119.2 (2)
C24—C25—H25	119.8	C42—N4—C41	115.3 (2)
C26—C25—H25	120.3	C20—O2—C2	116.43 (18)
C21—C26—C25	119.6 (3)	C30—O3—C3	116.05 (17)
O1—C1—C2—O2	176.3 (2)	O3—C30—C31—C32	−143.5 (2)
N1—C1—C2—O2	−5.7 (3)	O30—C30—C31—C36	−144.6 (3)
O1—C1—C2—C3	54.0 (3)	O3—C30—C31—C36	36.6 (3)
N1—C1—C2—C3	−128.0 (2)	C36—C31—C32—C33	−0.7 (4)
O2—C2—C3—O3	−59.8 (2)	C30—C31—C32—C33	179.4 (3)
C1—C2—C3—O3	63.3 (2)	C31—C32—C33—C34	2.3 (5)
O2—C2—C3—C4	58.8 (2)	C32—C33—C34—C35	−2.0 (6)
C1—C2—C3—C4	−178.06 (18)	C33—C34—C35—C36	0.0 (6)
O3—C3—C4—O4	18.2 (3)	C34—C35—C36—C31	1.6 (5)
C2—C3—C4—O4	−99.3 (3)	C32—C31—C36—C35	−1.3 (4)
O3—C3—C4—N4	−162.89 (19)	C30—C31—C36—C35	178.6 (3)
C2—C3—C4—N4	79.6 (3)	O1—C1—N1—C11	2.5 (4)
O20—C20—C21—C26	165.4 (3)	C2—C1—N1—C11	−175.4 (2)
O2—C20—C21—C26	−13.8 (3)	O4—C4—N4—C42	−176.8 (3)
O20—C20—C21—C22	−11.2 (5)	C3—C4—N4—C42	4.3 (4)
O2—C20—C21—C22	169.6 (3)	O4—C4—N4—C41	3.5 (4)
C26—C21—C22—C23	0.3 (5)	C3—C4—N4—C41	−175.3 (2)
C20—C21—C22—C23	177.1 (3)	O20—C20—O2—C2	−5.8 (4)
C21—C22—C23—C24	−1.2 (6)	C21—C20—O2—C2	173.40 (18)
C22—C23—C24—C25	1.1 (6)	C3—C2—O2—C20	−110.7 (2)
C23—C24—C25—C26	−0.3 (5)	C1—C2—O2—C20	126.8 (2)
C22—C21—C26—C25	0.5 (4)	O30—C30—O3—C3	5.8 (4)
C20—C21—C26—C25	−176.0 (3)	C31—C30—O3—C3	−175.35 (18)
C24—C25—C26—C21	−0.5 (4)	C2—C3—O3—C30	−155.48 (18)
O30—C30—C31—C32	35.3 (4)	C4—C3—O3—C30	83.6 (2)

(bom1) (R,R)-(-)-O,O'-Dibenzoyltartaric acid monoamide monomethylester

Crystal data

C19H17NO7	Dx = 1.306 Mg m^−3
Mr = 371.34	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 38 reflections
a = 7.193 (1) Å	θ = 11.5–13.9°
b = 14.515 (2) Å	µ = 0.10 mm^−1
c = 18.083 (2) Å	T = 293 K
V = 1888.0 (4) Å^3	Prism, colourless
Z = 4	0.7 × 0.6 × 0.6 mm
F(000) = 776

Data collection

KM-4 four circle diffractometer	Rint = 0.015
Radiation source: fine-focus sealed tube	θmax = 26.1°, θmin = 1.8°
Graphite monochromator	h = −8→8
Θ–2Θ scans	k = 0→17
3976 measured reflections	l = 0→22
2145 independent reflections	3 standard reflections every 100 reflections
1709 reflections with I > 2σ(I)	intensity decay: 2.1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.090	Calculated w = 1/[σ^2(Fo^2) + (0.0534P)^2 + 0.1331P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2145 reflections	Δρmax = 0.13 e Å^−3
244 parameters	Δρmin = −0.12 e Å^−3
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	−0.2644 (3)	0.48246 (15)	0.53306 (13)	0.0544 (5)
C2	−0.1100 (3)	0.54720 (15)	0.50830 (11)	0.0491 (5)
H2	−0.1627	0.5932	0.4764	0.050*
C3	−0.0168 (3)	0.59531 (14)	0.57273 (11)	0.0459 (4)
H3	−0.1091	0.6274	0.6011	0.050*
C4	0.1229 (3)	0.66472 (13)	0.54348 (10)	0.0433 (4)
C10	−0.3462 (5)	0.3313 (2)	0.5629 (2)	0.0965 (11)
H101	−0.3712	0.3438	0.6187	0.140*
H102	−0.3025	0.2694	0.5561	0.140*
H103	−0.4589	0.3388	0.5351	0.140*
C20	−0.0132 (3)	0.46667 (16)	0.40236 (11)	0.0549 (5)
C21	0.1376 (3)	0.41568 (15)	0.36611 (11)	0.0553 (6)
C22	0.1009 (5)	0.37242 (19)	0.29921 (13)	0.0776 (8)
H22	−0.0206	0.3769	0.2775	0.080*
C23	0.2398 (7)	0.3231 (2)	0.26407 (16)	0.0956 (12)
H23	0.2153	0.2929	0.2179	0.110*
C24	0.4139 (6)	0.3176 (2)	0.29506 (19)	0.0939 (11)
H24	0.5101	0.2834	0.2706	0.110*
C25	0.4508 (5)	0.36073 (18)	0.36054 (18)	0.0816 (8)
H25	0.5724	0.3565	0.3821	0.110*
C26	0.3121 (3)	0.40996 (16)	0.39596 (13)	0.0602 (6)
H26	0.3388	0.4406	0.4418	0.080*
C30	−0.0187 (3)	0.49977 (16)	0.68002 (11)	0.0530 (5)
C31	0.0966 (4)	0.43965 (14)	0.72731 (10)	0.0544 (5)
C32	0.0189 (5)	0.40893 (17)	0.79307 (12)	0.0721 (8)
H32	−0.1069	0.4247	0.8056	0.080*
C33	0.1251 (7)	0.35422 (19)	0.84023 (14)	0.0858 (11)
H33	0.0728	0.3323	0.8858	0.110*
C34	0.2998 (7)	0.3321 (2)	0.82293 (16)	0.0948 (11)
H34	0.3713	0.2948	0.8563	0.110*
C35	0.3791 (6)	0.3634 (2)	0.75829 (17)	0.0980 (11)
H35	0.5052	0.3475	0.7464	0.110*
C36	0.2779 (5)	0.41715 (19)	0.71048 (13)	0.0743 (8)
H36	0.3320	0.4392	0.6653	0.080*
N4	0.2994 (2)	0.65145 (13)	0.55836 (10)	0.0538 (5)
H41	0.3850	0.6914	0.5413	0.080*
H42	0.3348	0.6026	0.5856	0.080*
O1	−0.4163 (2)	0.50872 (12)	0.54705 (12)	0.0799 (5)
O2	0.03430 (18)	0.50116 (10)	0.46892 (7)	0.0493 (3)
O3	0.07664 (19)	0.53076 (9)	0.61982 (7)	0.0461 (3)
O4	0.0656 (2)	0.72970 (10)	0.50694 (10)	0.0648 (4)
O10	−0.2082 (2)	0.39661 (11)	0.53785 (10)	0.0655 (4)
O20	−0.1674 (3)	0.47659 (17)	0.37819 (10)	0.0852 (6)
O30	−0.1750 (3)	0.52134 (17)	0.69146 (10)	0.0835 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0388 (10)	0.0565 (12)	0.0678 (13)	0.0090 (9)	−0.0058 (10)	0.0073 (11)
C2	0.0369 (9)	0.0544 (11)	0.0559 (11)	0.0070 (9)	−0.0026 (9)	0.0090 (9)
C3	0.0405 (10)	0.0493 (10)	0.0480 (10)	0.0118 (9)	0.0072 (9)	0.0036 (9)
C4	0.0469 (10)	0.0410 (9)	0.0419 (9)	0.0100 (9)	0.0043 (9)	0.0005 (8)
C10	0.0860 (19)	0.0703 (16)	0.133 (3)	0.0007 (16)	0.020 (2)	0.0442 (18)
C20	0.0557 (12)	0.0650 (13)	0.0439 (10)	−0.0135 (11)	−0.0078 (10)	0.0087 (10)
C21	0.0724 (15)	0.0508 (11)	0.0427 (10)	−0.0194 (11)	0.0043 (10)	0.0000 (9)
C22	0.106 (2)	0.0757 (16)	0.0507 (13)	−0.0289 (17)	0.0016 (15)	−0.0036 (12)
C23	0.162 (4)	0.0689 (17)	0.0556 (16)	−0.034 (2)	0.032 (2)	−0.0185 (13)
C24	0.122 (3)	0.0614 (16)	0.098 (2)	−0.0226 (19)	0.050 (2)	−0.0209 (16)
C25	0.0807 (19)	0.0613 (14)	0.103 (2)	−0.0104 (14)	0.0280 (17)	−0.0188 (15)
C26	0.0659 (14)	0.0512 (12)	0.0634 (13)	−0.0105 (12)	0.0119 (12)	−0.0117 (11)
C30	0.0574 (13)	0.0601 (12)	0.0415 (10)	−0.0081 (11)	0.0080 (9)	−0.0021 (10)
C31	0.0810 (16)	0.0452 (10)	0.0370 (9)	−0.0095 (11)	0.0040 (11)	−0.0003 (9)
C32	0.108 (2)	0.0652 (13)	0.0425 (11)	−0.0291 (16)	0.0097 (13)	−0.0010 (11)
C33	0.158 (3)	0.0589 (14)	0.0406 (12)	−0.022 (2)	−0.0021 (18)	0.0094 (11)
C34	0.162 (4)	0.0637 (17)	0.0585 (17)	0.015 (2)	−0.021 (2)	0.0112 (13)
C35	0.126 (3)	0.094 (2)	0.0749 (17)	0.036 (2)	−0.008 (2)	0.0226 (16)
C36	0.098 (2)	0.0701 (15)	0.0551 (13)	0.0198 (16)	0.0088 (14)	0.0160 (12)
N4	0.0438 (9)	0.0539 (10)	0.0638 (11)	0.0018 (8)	0.0012 (8)	0.0193 (8)
O1	0.0362 (8)	0.0715 (10)	0.1319 (16)	0.0085 (8)	0.0060 (10)	0.0112 (11)
O2	0.0402 (7)	0.0637 (8)	0.0441 (7)	0.0032 (7)	−0.0039 (6)	−0.0026 (7)
O3	0.0475 (7)	0.0508 (7)	0.0399 (6)	0.0064 (6)	0.0069 (6)	0.0088 (6)
O4	0.0627 (9)	0.0527 (9)	0.0791 (10)	0.0164 (8)	−0.0013 (8)	0.0211 (8)
O10	0.0562 (8)	0.0576 (9)	0.0825 (11)	0.0083 (7)	0.0118 (9)	0.0196 (8)
O20	0.0641 (11)	0.1244 (16)	0.0672 (10)	−0.0046 (12)	−0.0246 (9)	0.0009 (11)
O30	0.0558 (10)	0.1283 (17)	0.0664 (10)	0.0055 (12)	0.0205 (9)	0.0193 (12)

Geometric parameters (Å, º)

C1—O1	1.185 (3)	C23—H23	0.9600
C1—O10	1.313 (3)	C24—C25	1.365 (4)
C1—C2	1.522 (3)	C24—H24	0.9600
C2—O2	1.425 (2)	C25—C26	1.384 (4)
C2—C3	1.515 (3)	C25—H25	0.9600
C2—H2	0.9600	C26—H26	0.9601
C3—O3	1.433 (2)	C30—O30	1.185 (3)
C3—C4	1.518 (3)	C30—O3	1.363 (2)
C3—H3	0.9600	C30—C31	1.477 (3)
C4—O4	1.223 (2)	C31—C36	1.379 (4)
C4—N4	1.312 (3)	C31—C32	1.388 (3)
C10—O10	1.445 (3)	C32—C33	1.393 (4)
C10—H101	1.0404	C32—H32	0.9600
C10—H102	0.9599	C33—C34	1.334 (6)
C10—H103	0.9600	C33—H33	0.9599
C20—O20	1.201 (3)	C34—C35	1.378 (5)
C20—O2	1.348 (3)	C34—H34	0.9599
C20—C21	1.468 (3)	C35—C36	1.373 (4)
C21—C26	1.369 (3)	C35—H35	0.9600
C21—C22	1.388 (3)	C36—H36	0.9600
C22—C23	1.384 (5)	N4—H41	0.9001
C22—H22	0.9599	N4—H42	0.9000
C23—C24	1.374 (5)
O1—C1—O10	125.1 (2)	C25—C24—C23	120.3 (3)
O1—C1—C2	122.5 (2)	C25—C24—H24	119.8
O10—C1—C2	112.38 (17)	C23—C24—H24	119.9
O2—C2—C3	106.14 (15)	C24—C25—C26	119.9 (3)
O2—C2—C1	112.89 (17)	C24—C25—H25	120.0
C3—C2—C1	112.42 (17)	C26—C25—H25	120.1
O2—C2—H2	108.3	C21—C26—C25	120.6 (2)
C3—C2—H2	108.4	C21—C26—H26	119.7
C1—C2—H2	108.5	C25—C26—H26	119.6
O3—C3—C2	111.29 (16)	O30—C30—O3	122.0 (2)
O3—C3—C4	109.32 (15)	O30—C30—C31	126.0 (2)
C2—C3—C4	109.34 (16)	O3—C30—C31	112.01 (19)
O3—C3—H3	108.8	C36—C31—C32	119.6 (3)
C2—C3—H3	109.2	C36—C31—C30	122.9 (2)
C4—C3—H3	108.8	C32—C31—C30	117.4 (3)
O4—C4—N4	123.4 (2)	C31—C32—C33	119.1 (3)
O4—C4—C3	118.51 (18)	C31—C32—H32	120.3
N4—C4—C3	118.13 (17)	C33—C32—H32	120.5
O10—C10—H101	108.0	C34—C33—C32	120.7 (3)
O10—C10—H102	110.4	C34—C33—H33	119.3
H101—C10—H102	110.1	C32—C33—H33	120.0
O10—C10—H103	109.9	C33—C34—C35	120.7 (3)
H101—C10—H103	110.1	C33—C34—H34	119.5
H102—C10—H103	108.4	C35—C34—H34	119.8
O20—C20—O2	121.0 (2)	C36—C35—C34	120.1 (4)
O20—C20—C21	125.5 (2)	C36—C35—H35	119.8
O2—C20—C21	113.51 (19)	C34—C35—H35	120.1
C26—C21—C22	119.4 (3)	C35—C36—C31	119.8 (3)
C26—C21—C20	122.15 (19)	C35—C36—H36	120.7
C22—C21—C20	118.5 (2)	C31—C36—H36	119.5
C23—C22—C21	119.8 (3)	C4—N4—H41	119.8
C23—C22—H22	120.3	C4—N4—H42	120.2
C21—C22—H22	119.9	H41—N4—H42	120.0
C24—C23—C22	120.0 (3)	C20—O2—C2	115.84 (16)
C24—C23—H23	119.7	C30—O3—C3	117.03 (16)
C22—C23—H23	120.2	C1—O10—C10	115.57 (19)
O1—C1—C2—O2	−158.0 (2)	C24—C25—C26—C21	0.2 (4)
O10—C1—C2—O2	23.0 (3)	O30—C30—C31—C36	179.8 (3)
O1—C1—C2—C3	81.9 (3)	O3—C30—C31—C36	−1.2 (3)
O10—C1—C2—C3	−97.1 (2)	O30—C30—C31—C32	−3.4 (4)
O2—C2—C3—O3	−59.67 (19)	O3—C30—C31—C32	175.63 (19)
C1—C2—C3—O3	64.2 (2)	C36—C31—C32—C33	−1.3 (4)
O2—C2—C3—C4	61.19 (19)	C30—C31—C32—C33	−178.2 (2)
C1—C2—C3—C4	−174.94 (15)	C31—C32—C33—C34	0.6 (4)
O3—C3—C4—O4	−174.23 (17)	C32—C33—C34—C35	0.4 (5)
C2—C3—C4—O4	63.7 (2)	C33—C34—C35—C36	−0.7 (5)
O3—C3—C4—N4	6.2 (2)	C34—C35—C36—C31	−0.1 (5)
C2—C3—C4—N4	−115.8 (2)	C32—C31—C36—C35	1.0 (4)
O20—C20—C21—C26	177.7 (3)	C30—C31—C36—C35	177.8 (3)
O2—C20—C21—C26	−4.1 (3)	O20—C20—O2—C2	1.5 (3)
O20—C20—C21—C22	−2.0 (4)	C21—C20—O2—C2	−176.83 (17)
O2—C20—C21—C22	176.22 (19)	C3—C2—O2—C20	−169.20 (16)
C26—C21—C22—C23	0.9 (4)	C1—C2—O2—C20	67.2 (2)
C20—C21—C22—C23	−179.4 (2)	O30—C30—O3—C3	3.6 (3)
C21—C22—C23—C24	−0.5 (4)	C31—C30—O3—C3	−175.47 (17)
C22—C23—C24—C25	0.0 (5)	C2—C3—O3—C30	−95.13 (19)
C23—C24—C25—C26	0.2 (4)	C4—C3—O3—C30	144.00 (17)
C22—C21—C26—C25	−0.8 (4)	O1—C1—O10—C10	−0.5 (4)
C20—C21—C26—C25	179.6 (2)	C2—C1—O10—C10	178.5 (2)

(bom3) (R,R)-(-)-O,O'-Dibenzoyltartaric acid mono(N,N-dimethylamide) monomethylester

Crystal data

C21H21NO7	F(000) = 420
Mr = 399.39	Dx = 1.338 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54178 Å
a = 8.127 (1) Å	Cell parameters from 25 reflections
b = 14.109 (2) Å	θ = 12.0–19.9°
c = 8.733 (1) Å	µ = 0.85 mm^−1
β = 97.97 (1)°	T = 293 K
V = 991.7 (2) Å^3	Plate, colourless
Z = 2	0.8 × 0.4 × 0.3 mm

Data collection

KM-4 four circle diffractometer	Rint = 0.030
Radiation source: fine-focus sealed tube	θmax = 64.9°, θmin = 5.1°
Graphite monochromator	h = −9→9
Θ–2Θ scans	k = −16→16
3222 measured reflections	l = −10→0
3110 independent reflections	2 standard reflections every 100 reflections
3016 reflections with I > 2σ(I)	intensity decay: 0.8%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.033	Calculated w = 1/[σ^2(Fo^2) + (0.0624P)^2 + 0.0749P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.089	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.17 e Å^−3
3110 reflections	Δρmin = −0.17 e Å^−3
263 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0221 (12)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.28 (15)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.3415 (2)	0.52804 (12)	0.3065 (2)	0.0443 (4)
C2	0.4593 (2)	0.50098 (12)	0.45013 (17)	0.0397 (3)
H2	0.5444	0.4603	0.4210	0.040*
C3	0.5404 (2)	0.58867 (11)	0.53249 (18)	0.0390 (3)
H3	0.5919	0.6263	0.4608	0.040*
C4	0.67080 (19)	0.56146 (11)	0.67095 (17)	0.0389 (3)
C10	0.3336 (3)	0.5746 (3)	0.0468 (2)	0.0816 (8)
H101	0.2578	0.6249	0.0617	0.110*
H102	0.2732	0.5198	0.0051	0.110*
H103	0.4066	0.5942	−0.0248	0.110*
C20	0.4407 (2)	0.37471 (11)	0.62577 (19)	0.0441 (4)
C21	0.3204 (2)	0.31809 (11)	0.7005 (2)	0.0454 (4)
C22	0.3781 (3)	0.26559 (17)	0.8303 (3)	0.0665 (6)
H22	0.4939	0.2672	0.8712	0.060*
C23	0.2693 (4)	0.2111 (2)	0.9005 (3)	0.0846 (8)
H23	0.3087	0.1760	0.9925	0.090*
C24	0.1057 (4)	0.20666 (18)	0.8404 (3)	0.0749 (7)
H24	0.0303	0.1687	0.8897	0.090*
C25	0.0476 (3)	0.25662 (18)	0.7103 (3)	0.0713 (6)
H25	−0.0675	0.2522	0.6673	0.090*
C26	0.1548 (3)	0.31291 (15)	0.6393 (2)	0.0579 (5)
H26	0.1136	0.3482	0.5480	0.060*
C30	0.4562 (2)	0.72413 (11)	0.65773 (18)	0.0408 (4)
C31	0.3187 (2)	0.76799 (11)	0.72762 (19)	0.0419 (4)
C32	0.3574 (3)	0.84408 (13)	0.8269 (2)	0.0508 (4)
H32	0.4699	0.8664	0.8476	0.060*
C33	0.2342 (3)	0.88773 (16)	0.8961 (3)	0.0675 (6)
H33	0.2603	0.9408	0.9639	0.090*
C34	0.0736 (3)	0.85526 (19)	0.8658 (3)	0.0720 (6)
H34	−0.0120	0.8847	0.9148	0.090*
C35	0.0343 (3)	0.78038 (19)	0.7674 (3)	0.0695 (6)
H35	−0.0784	0.7586	0.7460	0.090*
C36	0.1566 (2)	0.73613 (15)	0.6985 (2)	0.0552 (5)
H36	0.1299	0.6831	0.6308	0.060*
C41	0.9433 (2)	0.50997 (18)	0.7719 (2)	0.0631 (5)
H411	0.9119	0.4570	0.7985	0.110*
H412	0.9465	0.5542	0.8558	0.110*
H413	1.0526	0.5056	0.7426	0.110*
C42	0.8695 (2)	0.52504 (17)	0.4882 (2)	0.0611 (5)
H421	0.8566	0.4593	0.4610	0.090*
H422	0.9825	0.5440	0.4859	0.090*
H423	0.7994	0.5628	0.4144	0.090*
N4	0.82432 (16)	0.54087 (11)	0.64164 (15)	0.0443 (3)
O1	0.19441 (17)	0.52637 (15)	0.29316 (18)	0.0811 (6)
O2	0.36355 (15)	0.44940 (8)	0.54709 (14)	0.0436 (3)
O3	0.40971 (14)	0.64119 (8)	0.58640 (13)	0.0436 (3)
O4	0.63072 (15)	0.56063 (10)	0.80091 (13)	0.0512 (3)
O10	0.42805 (15)	0.55154 (13)	0.19504 (14)	0.0599 (4)
O20	0.58681 (17)	0.35861 (10)	0.63187 (17)	0.0577 (3)
O30	0.59353 (16)	0.75669 (9)	0.66181 (15)	0.0510 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0407 (8)	0.0535 (10)	0.0391 (8)	0.0013 (7)	0.0069 (7)	−0.0030 (6)
C2	0.0426 (8)	0.0437 (8)	0.0339 (8)	0.0020 (7)	0.0098 (6)	−0.0016 (6)
C3	0.0413 (8)	0.0411 (8)	0.0361 (8)	0.0018 (6)	0.0100 (6)	0.0001 (6)
C4	0.0442 (8)	0.0374 (7)	0.0359 (8)	−0.0013 (6)	0.0085 (6)	−0.0027 (6)
C10	0.0631 (12)	0.140 (3)	0.0403 (10)	−0.0021 (15)	0.0020 (9)	0.0218 (13)
C20	0.0531 (10)	0.0384 (9)	0.0393 (8)	0.0017 (7)	0.0011 (7)	−0.0046 (7)
C21	0.0608 (11)	0.0376 (8)	0.0377 (8)	0.0012 (7)	0.0069 (7)	−0.0029 (6)
C22	0.0744 (14)	0.0705 (13)	0.0517 (11)	−0.0039 (11)	−0.0019 (10)	0.0157 (10)
C23	0.112 (2)	0.0866 (18)	0.0546 (13)	−0.0084 (15)	0.0082 (13)	0.0281 (12)
C24	0.0919 (18)	0.0693 (14)	0.0671 (14)	−0.0162 (12)	0.0240 (13)	0.0125 (11)
C25	0.0653 (13)	0.0748 (14)	0.0758 (15)	−0.0129 (11)	0.0165 (11)	0.0031 (11)
C26	0.0615 (12)	0.0572 (11)	0.0543 (11)	−0.0018 (9)	0.0050 (9)	0.0093 (9)
C30	0.0496 (9)	0.0369 (7)	0.0353 (8)	0.0005 (7)	0.0037 (7)	0.0028 (6)
C31	0.0501 (9)	0.0390 (8)	0.0360 (8)	0.0033 (7)	0.0038 (7)	0.0025 (6)
C32	0.0604 (11)	0.0450 (9)	0.0472 (10)	−0.0017 (8)	0.0078 (8)	−0.0030 (7)
C33	0.0890 (16)	0.0554 (11)	0.0602 (13)	0.0102 (11)	0.0178 (11)	−0.0127 (9)
C34	0.0729 (14)	0.0823 (16)	0.0627 (13)	0.0262 (12)	0.0156 (11)	−0.0107 (11)
C35	0.0484 (11)	0.0936 (17)	0.0664 (13)	0.0100 (11)	0.0081 (9)	−0.0084 (12)
C36	0.0497 (10)	0.0614 (11)	0.0539 (11)	0.0018 (8)	0.0055 (8)	−0.0104 (8)
C41	0.0523 (11)	0.0801 (13)	0.0542 (11)	0.0112 (10)	−0.0021 (9)	0.0045 (10)
C42	0.0483 (9)	0.0884 (15)	0.0493 (10)	0.0062 (10)	0.0164 (8)	−0.0005 (9)
N4	0.0397 (7)	0.0540 (8)	0.0389 (7)	−0.0001 (6)	0.0042 (6)	−0.0004 (6)
O1	0.0434 (7)	0.1419 (18)	0.0582 (8)	−0.0016 (9)	0.0074 (6)	0.0203 (9)
O2	0.0493 (6)	0.0393 (6)	0.0439 (6)	0.0015 (5)	0.0124 (5)	0.0028 (5)
O3	0.0431 (6)	0.0401 (6)	0.0478 (7)	0.0022 (5)	0.0074 (5)	−0.0052 (5)
O4	0.0619 (7)	0.0582 (7)	0.0349 (6)	0.0063 (6)	0.0118 (5)	−0.0010 (5)
O10	0.0451 (6)	0.0946 (10)	0.0400 (6)	0.0018 (7)	0.0065 (5)	0.0154 (7)
O20	0.0535 (8)	0.0563 (8)	0.0617 (8)	0.0059 (6)	0.0022 (6)	0.0023 (6)
O30	0.0476 (7)	0.0494 (7)	0.0568 (8)	−0.0069 (5)	0.0100 (6)	−0.0014 (5)

Geometric parameters (Å, º)

C1—O1	1.185 (2)	C25—C26	1.387 (3)
C1—O10	1.320 (2)	C25—H25	0.9600
C1—C2	1.518 (2)	C26—H26	0.9600
C2—O2	1.4266 (19)	C30—O30	1.203 (2)
C2—C3	1.533 (2)	C30—O3	1.355 (2)
C2—H2	0.9600	C30—C31	1.481 (2)
C3—O3	1.4276 (19)	C31—C36	1.381 (3)
C3—C4	1.542 (2)	C31—C32	1.389 (3)
C3—H3	0.9599	C32—C33	1.383 (3)
C4—O4	1.2234 (18)	C32—H32	0.9600
C4—N4	1.340 (2)	C33—C34	1.374 (4)
C10—O10	1.448 (2)	C33—H33	0.9600
C10—H101	0.9601	C34—C35	1.371 (4)
C10—H102	0.9600	C34—H34	0.9600
C10—H103	0.9600	C35—C36	1.380 (3)
C20—O20	1.203 (2)	C35—H35	0.9600
C20—O2	1.362 (2)	C36—H36	0.9600
C20—C21	1.482 (3)	C41—N4	1.454 (3)
C21—C26	1.379 (3)	C41—H411	0.8334
C21—C22	1.381 (3)	C41—H412	0.9600
C22—C23	1.378 (3)	C41—H413	0.9600
C22—H22	0.9600	C42—N4	1.455 (2)
C23—C24	1.361 (4)	C42—H421	0.9600
C23—H23	0.9600	C42—H422	0.9600
C24—C25	1.365 (4)	C42—H423	0.9599
C24—H24	0.9600
O1—C1—O10	124.50 (17)	C21—C26—C25	119.8 (2)
O1—C1—C2	126.04 (16)	C21—C26—H26	120.2
O10—C1—C2	109.43 (13)	C25—C26—H26	119.9
O2—C2—C1	106.57 (13)	O30—C30—O3	122.82 (15)
O2—C2—C3	111.57 (12)	O30—C30—C31	125.33 (15)
C1—C2—C3	111.45 (13)	O3—C30—C31	111.85 (14)
O2—C2—H2	108.9	C36—C31—C32	119.63 (16)
C1—C2—H2	109.1	C36—C31—C30	122.87 (15)
C3—C2—H2	109.2	C32—C31—C30	117.50 (16)
O3—C3—C2	106.40 (12)	C33—C32—C31	120.1 (2)
O3—C3—C4	109.42 (12)	C33—C32—H32	120.0
C2—C3—C4	111.78 (12)	C31—C32—H32	119.9
O3—C3—H3	109.8	C34—C33—C32	119.6 (2)
C2—C3—H3	109.8	C34—C33—H33	120.1
C4—C3—H3	109.6	C32—C33—H33	120.4
O4—C4—N4	123.36 (15)	C35—C34—C33	120.63 (19)
O4—C4—C3	119.18 (14)	C35—C34—H34	119.5
N4—C4—C3	117.46 (13)	C33—C34—H34	119.8
O10—C10—H101	108.4	C34—C35—C36	120.2 (2)
O10—C10—H102	109.7	C34—C35—H35	120.1
H101—C10—H102	110.0	C36—C35—H35	119.7
O10—C10—H103	110.4	C35—C36—C31	119.88 (19)
H101—C10—H103	110.0	C35—C36—H36	120.4
H102—C10—H103	108.4	C31—C36—H36	119.7
O20—C20—O2	123.42 (16)	N4—C41—H411	106.9
O20—C20—C21	125.88 (16)	N4—C41—H412	110.3
O2—C20—C21	110.70 (15)	H411—C41—H412	110.3
C26—C21—C22	119.43 (19)	N4—C41—H413	110.5
C26—C21—C20	121.73 (16)	H411—C41—H413	110.3
C22—C21—C20	118.76 (18)	H412—C41—H413	108.5
C23—C22—C21	119.9 (2)	N4—C42—H421	110.1
C23—C22—H22	120.3	N4—C42—H422	109.9
C21—C22—H22	119.8	H421—C42—H422	109.6
C24—C23—C22	120.4 (2)	N4—C42—H423	109.3
C24—C23—H23	119.6	H421—C42—H423	109.6
C22—C23—H23	120.0	H422—C42—H423	108.2
C23—C24—C25	120.3 (2)	C4—N4—C41	116.85 (14)
C23—C24—H24	120.2	C4—N4—C42	124.73 (14)
C25—C24—H24	119.5	C41—N4—C42	116.69 (15)
C24—C25—C26	120.1 (2)	C20—O2—C2	116.30 (13)
C24—C25—H25	119.9	C30—O3—C3	115.29 (13)
C26—C25—H25	120.0	C1—O10—C10	116.44 (15)
O1—C1—C2—O2	15.8 (3)	O30—C30—C31—C32	−11.2 (2)
O10—C1—C2—O2	−162.37 (14)	O3—C30—C31—C32	168.90 (14)
O1—C1—C2—C3	−106.1 (2)	C36—C31—C32—C33	−0.1 (3)
O10—C1—C2—C3	75.69 (18)	C30—C31—C32—C33	−179.79 (18)
O2—C2—C3—O3	−53.80 (15)	C31—C32—C33—C34	0.0 (3)
C1—C2—C3—O3	65.20 (15)	C32—C33—C34—C35	−0.3 (4)
O2—C2—C3—C4	65.60 (16)	C33—C34—C35—C36	0.6 (4)
C1—C2—C3—C4	−175.40 (13)	C34—C35—C36—C31	−0.6 (4)
O3—C3—C4—O4	20.9 (2)	C32—C31—C36—C35	0.4 (3)
C2—C3—C4—O4	−96.66 (17)	C30—C31—C36—C35	−179.92 (18)
O3—C3—C4—N4	−158.29 (14)	O4—C4—N4—C41	4.3 (3)
C2—C3—C4—N4	84.11 (17)	C3—C4—N4—C41	−176.51 (17)
O20—C20—C21—C26	−151.1 (2)	O4—C4—N4—C42	168.77 (18)
O2—C20—C21—C26	29.0 (2)	C3—C4—N4—C42	−12.0 (2)
O20—C20—C21—C22	25.7 (3)	O20—C20—O2—C2	9.5 (2)
O2—C20—C21—C22	−154.32 (18)	C21—C20—O2—C2	−170.52 (13)
C26—C21—C22—C23	−2.1 (3)	C1—C2—O2—C20	142.16 (14)
C20—C21—C22—C23	−178.9 (2)	C3—C2—O2—C20	−95.97 (15)
C21—C22—C23—C24	1.7 (4)	O30—C30—O3—C3	7.5 (2)
C22—C23—C24—C25	−0.4 (4)	C31—C30—O3—C3	−172.65 (12)
C23—C24—C25—C26	−0.6 (4)	C2—C3—O3—C30	−177.45 (12)
C22—C21—C26—C25	1.2 (3)	C4—C3—O3—C30	61.63 (16)
C20—C21—C26—C25	177.93 (19)	O1—C1—O10—C10	−1.3 (3)
C24—C25—C26—C21	0.1 (4)	C2—C1—O10—C10	176.9 (2)
O30—C30—C31—C36	169.09 (18)	C20—O20—C30^i—O30^i	9.00 (15)
O3—C30—C31—C36	−10.8 (2)	C30^i—O30^i—C20—O20	9.46 (16)

Symmetry code: (i) −x+1, y−1/2, −z+1.

(bcn3) N,N-Dimethyl(2R,3S)-2,3-dibenzoyloxy-3-cyanopropanamide

Crystal data

C20H18N2O5	F(000) = 384
Mr = 366.36	Dx = 1.306 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 7.749 (2) Å	Cell parameters from 15 reflections
b = 14.144 (4) Å	θ = 6.0–17.3°
c = 9.063 (2) Å	µ = 0.10 mm^−1
β = 110.34 (2)°	T = 293 K
V = 931.4 (4) Å^3	Plate, colourless
Z = 2	0.5 × 0.4 × 0.4 mm

Data collection

Syntex P21 diffractometer	Rint = 0.033
Radiation source: fine-focus sealed tube	θmax = 27.6°, θmin = 2.4°
Graphite monochromator	h = 0→9
Θ–2Θ scans	k = −17→17
3921 measured reflections	l = −11→11
2129 independent reflections	2 standard reflections every 100 reflections
1423 reflections with I > 2σ(I)	intensity decay: 4.4%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.044	Calculated w = 1/[σ^2(Fo^2) + (0.0503P)^2 + 0.092P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.107	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.12 e Å^−3
2129 reflections	Δρmin = −0.12 e Å^−3
245 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.036 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.3064 (5)	0.6552 (3)	0.3428 (4)	0.0619 (9)
C2	0.4712 (5)	0.6247 (2)	0.4762 (4)	0.0547 (8)
H2	0.5489	0.5881	0.4354	0.050*
C3	0.5782 (5)	0.7097 (2)	0.5649 (4)	0.0503 (8)
H3	0.6192	0.7473	0.4953	0.050*
C4	0.7450 (4)	0.6810 (2)	0.7081 (3)	0.0525 (8)
C20	0.5104 (6)	0.4865 (2)	0.6349 (4)	0.0561 (8)
C21	0.4133 (5)	0.4224 (2)	0.7081 (4)	0.0576 (9)
C22	0.5187 (6)	0.3547 (3)	0.8138 (4)	0.0709 (11)
H22	0.6489	0.3510	0.8355	0.070*
C23	0.4340 (8)	0.2936 (3)	0.8851 (5)	0.0831 (13)
H23	0.5049	0.2474	0.9589	0.120*
C24	0.2486 (9)	0.2974 (3)	0.8536 (5)	0.0854 (14)
H24	0.1928	0.2547	0.9062	0.120*
C25	0.1424 (7)	0.3631 (3)	0.7467 (6)	0.0829 (13)
H25	0.0118	0.3654	0.7237	0.120*
C26	0.2253 (6)	0.4251 (3)	0.6754 (5)	0.0697 (10)
H26	0.1530	0.4703	0.6001	0.070*
C30	0.5198 (5)	0.8502 (2)	0.6770 (4)	0.0514 (8)
C31	0.3969 (5)	0.9021 (2)	0.7418 (4)	0.0513 (8)
C32	0.4721 (6)	0.9787 (2)	0.8396 (4)	0.0600 (9)
H32	0.5989	0.9953	0.8628	0.070*
C33	0.3638 (7)	1.0297 (3)	0.9052 (5)	0.0748 (12)
H33	0.4159	1.0816	0.9749	0.120*
C34	0.1853 (7)	1.0062 (4)	0.8714 (5)	0.0835 (13)
H34	0.1115	1.0427	0.9164	0.120*
C35	0.1098 (6)	0.9319 (4)	0.7744 (6)	0.0939 (15)
H35	−0.0183	0.9177	0.7497	0.120*
C36	0.2158 (5)	0.8782 (3)	0.7103 (5)	0.0728 (11)
H36	0.1645	0.8240	0.6462	0.070*
C41	1.0595 (5)	0.6330 (4)	0.8212 (4)	0.0834 (13)
H411	1.0575	0.6651	0.9139	0.120*
H412	1.1725	0.6468	0.8043	0.120*
H413	1.0533	0.5659	0.8350	0.120*
C42	0.9216 (5)	0.6524 (4)	0.5312 (4)	0.0750 (11)
H421	1.0477	0.6646	0.5435	0.120*
H422	0.8422	0.6962	0.4576	0.120*
H423	0.8880	0.5894	0.4925	0.120*
N1	0.1844 (5)	0.6776 (3)	0.2385 (4)	0.0863 (10)
N4	0.9032 (3)	0.6630 (2)	0.6848 (3)	0.0567 (7)
O2	0.4026 (3)	0.56466 (15)	0.5714 (3)	0.0576 (6)
O3	0.4524 (3)	0.76432 (14)	0.6158 (2)	0.0518 (6)
O4	0.7270 (3)	0.6761 (2)	0.8372 (2)	0.0670 (7)
O20	0.6591 (4)	0.47527 (19)	0.6266 (3)	0.0713 (7)
O30	0.6642 (4)	0.87897 (18)	0.6745 (3)	0.0669 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.071 (2)	0.066 (2)	0.0481 (19)	−0.0067 (19)	0.0202 (18)	−0.0021 (17)
C2	0.066 (2)	0.0545 (19)	0.0482 (17)	0.0014 (17)	0.0260 (16)	−0.0009 (15)
C3	0.0606 (19)	0.0448 (18)	0.0497 (16)	0.0041 (14)	0.0245 (15)	−0.0007 (14)
C4	0.0632 (19)	0.0489 (19)	0.0442 (17)	0.0047 (16)	0.0171 (14)	0.0009 (14)
C20	0.072 (2)	0.0429 (18)	0.0493 (17)	0.0029 (17)	0.0158 (17)	−0.0069 (15)
C21	0.081 (3)	0.0425 (17)	0.0469 (18)	0.0007 (17)	0.0187 (17)	−0.0046 (14)
C22	0.096 (3)	0.045 (2)	0.060 (2)	−0.0002 (19)	0.012 (2)	−0.0026 (17)
C23	0.118 (4)	0.054 (2)	0.058 (2)	−0.010 (2)	0.008 (2)	0.0018 (18)
C24	0.132 (4)	0.060 (3)	0.065 (3)	−0.020 (3)	0.035 (3)	0.003 (2)
C25	0.096 (3)	0.070 (3)	0.091 (3)	−0.010 (2)	0.042 (3)	0.005 (2)
C26	0.085 (3)	0.054 (2)	0.071 (2)	0.0052 (19)	0.027 (2)	0.0120 (19)
C30	0.056 (2)	0.0464 (18)	0.0500 (18)	−0.0047 (16)	0.0162 (16)	0.0011 (15)
C31	0.059 (2)	0.0418 (18)	0.0520 (17)	0.0021 (15)	0.0186 (15)	0.0022 (15)
C32	0.075 (2)	0.0468 (18)	0.0604 (19)	−0.0001 (18)	0.0268 (18)	0.0043 (17)
C33	0.104 (4)	0.052 (2)	0.067 (2)	0.010 (2)	0.029 (2)	0.0002 (19)
C34	0.092 (3)	0.084 (3)	0.077 (3)	0.029 (3)	0.032 (2)	−0.006 (2)
C35	0.062 (2)	0.120 (4)	0.103 (3)	0.008 (3)	0.033 (2)	−0.019 (3)
C36	0.060 (2)	0.075 (3)	0.084 (3)	−0.003 (2)	0.0249 (19)	−0.024 (2)
C41	0.072 (2)	0.102 (4)	0.066 (2)	0.019 (2)	0.0106 (19)	−0.003 (2)
C42	0.075 (2)	0.094 (3)	0.063 (2)	0.011 (2)	0.0336 (17)	0.002 (2)
N1	0.083 (2)	0.097 (3)	0.0652 (19)	−0.005 (2)	0.0081 (18)	0.004 (2)
N4	0.0582 (15)	0.0604 (16)	0.0504 (14)	0.0058 (15)	0.0173 (12)	−0.0010 (14)
O2	0.0736 (15)	0.0434 (13)	0.0604 (13)	0.0019 (11)	0.0292 (11)	0.0011 (11)
O3	0.0548 (14)	0.0435 (12)	0.0593 (12)	0.0007 (10)	0.0227 (11)	−0.0019 (10)
O4	0.0838 (15)	0.0741 (17)	0.0468 (13)	0.0097 (14)	0.0275 (11)	0.0005 (12)
O20	0.0717 (18)	0.0611 (16)	0.0831 (17)	0.0078 (13)	0.0295 (14)	−0.0006 (13)
O30	0.0601 (16)	0.0615 (16)	0.0832 (17)	−0.0095 (12)	0.0301 (13)	−0.0066 (13)

Geometric parameters (Å, º)

C1—N1	1.125 (4)	C26—H26	0.9600
C1—C2	1.485 (5)	C30—O30	1.198 (4)
C2—O2	1.438 (4)	C30—O3	1.362 (4)
C2—C3	1.522 (4)	C30—C31	1.476 (5)
C2—H2	0.9601	C31—C36	1.374 (5)
C3—O3	1.440 (4)	C31—C32	1.392 (5)
C3—C4	1.534 (4)	C32—C33	1.387 (6)
C3—H3	0.9600	C32—H32	0.9600
C4—O4	1.228 (4)	C33—C34	1.350 (6)
C4—N4	1.339 (4)	C33—H33	0.9601
C20—O20	1.191 (4)	C34—C35	1.365 (7)
C20—O2	1.385 (4)	C34—H34	0.9599
C20—C21	1.475 (5)	C35—C36	1.386 (6)
C21—C26	1.382 (6)	C35—H35	0.9600
C21—C22	1.399 (5)	C36—H36	0.9600
C22—C23	1.375 (6)	C41—N4	1.461 (4)
C22—H22	0.9600	C41—H411	0.9600
C23—C24	1.365 (7)	C41—H412	0.9600
C23—H23	0.9600	C41—H413	0.9599
C24—C25	1.388 (7)	C42—N4	1.455 (4)
C24—H24	0.9599	C42—H421	0.9600
C25—C26	1.375 (6)	C42—H422	0.9600
C25—H25	0.9600	C42—H423	0.9600
N1—C1—C2	177.8 (4)	O30—C30—C31	125.1 (3)
O2—C2—C1	105.5 (3)	O3—C30—C31	113.3 (3)
O2—C2—C3	113.4 (2)	C36—C31—C32	119.7 (3)
C1—C2—C3	110.9 (3)	C36—C31—C30	123.3 (3)
O2—C2—H2	109.0	C32—C31—C30	117.0 (3)
C1—C2—H2	108.6	C33—C32—C31	119.7 (4)
C3—C2—H2	109.2	C33—C32—H32	120.2
O3—C3—C2	106.7 (3)	C31—C32—H32	120.0
O3—C3—C4	109.6 (2)	C34—C33—C32	119.9 (4)
C2—C3—C4	112.5 (3)	C34—C33—H33	120.0
O3—C3—H3	109.3	C32—C33—H33	120.1
C2—C3—H3	109.5	C33—C34—C35	120.8 (4)
C4—C3—H3	109.2	C33—C34—H34	119.1
O4—C4—N4	123.6 (3)	C35—C34—H34	120.2
O4—C4—C3	118.7 (3)	C34—C35—C36	120.6 (4)
N4—C4—C3	117.7 (3)	C34—C35—H35	119.2
O20—C20—O2	122.5 (3)	C36—C35—H35	120.3
O20—C20—C21	127.1 (4)	C31—C36—C35	119.3 (4)
O2—C20—C21	110.5 (3)	C31—C36—H36	120.1
C26—C21—C22	119.2 (4)	C35—C36—H36	120.7
C26—C21—C20	123.4 (3)	N4—C41—H411	110.0
C22—C21—C20	117.4 (4)	N4—C41—H412	109.8
C23—C22—C21	119.4 (4)	H411—C41—H412	109.7
C23—C22—H22	120.6	N4—C41—H413	109.5
C21—C22—H22	120.0	H411—C41—H413	109.7
C24—C23—C22	121.2 (4)	H412—C41—H413	108.2
C24—C23—H23	118.6	N4—C42—H421	107.7
C22—C23—H23	120.2	N4—C42—H422	110.3
C23—C24—C25	119.8 (4)	H421—C42—H422	110.2
C23—C24—H24	119.7	N4—C42—H423	110.0
C25—C24—H24	120.5	H421—C42—H423	110.2
C26—C25—C24	119.7 (5)	H422—C42—H423	108.5
C26—C25—H25	120.4	C4—N4—C42	124.7 (3)
C24—C25—H25	119.9	C4—N4—C41	117.2 (3)
C25—C26—C21	120.7 (4)	C42—N4—C41	116.8 (3)
C25—C26—H26	120.4	C20—O2—C2	115.2 (3)
C21—C26—H26	118.8	C30—O3—C3	113.7 (3)
O30—C30—O3	121.6 (3)
O2—C2—C3—O3	−61.3 (3)	O3—C30—C31—C32	164.8 (3)
C1—C2—C3—O3	57.3 (3)	C36—C31—C32—C33	0.4 (5)
O2—C2—C3—C4	59.0 (4)	C30—C31—C32—C33	−179.5 (3)
C1—C2—C3—C4	177.5 (3)	C31—C32—C33—C34	−1.3 (6)
O3—C3—C4—O4	24.8 (4)	C32—C33—C34—C35	0.7 (6)
C2—C3—C4—O4	−93.8 (4)	C33—C34—C35—C36	0.9 (8)
O3—C3—C4—N4	−155.0 (3)	C32—C31—C36—C35	1.1 (6)
C2—C3—C4—N4	86.4 (4)	C30—C31—C36—C35	−179.0 (4)
O20—C20—C21—C26	−160.7 (4)	C34—C35—C36—C31	−1.8 (7)
O2—C20—C21—C26	18.4 (5)	O4—C4—N4—C42	168.9 (4)
O20—C20—C21—C22	18.1 (5)	C3—C4—N4—C42	−11.3 (5)
O2—C20—C21—C22	−162.8 (3)	O4—C4—N4—C41	2.0 (5)
C26—C21—C22—C23	−1.3 (5)	C3—C4—N4—C41	−178.2 (3)
C20—C21—C22—C23	179.8 (3)	O20—C20—O2—C2	8.2 (4)
C21—C22—C23—C24	0.6 (6)	C21—C20—O2—C2	−170.9 (3)
C22—C23—C24—C25	0.6 (6)	C1—C2—O2—C20	141.3 (3)
C23—C24—C25—C26	−1.1 (6)	C3—C2—O2—C20	−97.1 (3)
C24—C25—C26—C21	0.4 (6)	O30—C30—O3—C3	6.0 (4)
C22—C21—C26—C25	0.8 (6)	C31—C30—O3—C3	−174.9 (2)
C20—C21—C26—C25	179.6 (3)	C2—C3—O3—C30	−170.8 (2)
O30—C30—C31—C36	164.0 (4)	C4—C3—O3—C30	67.2 (3)
O3—C30—C31—C36	−15.1 (4)	C20—O20—C30^i—O30^i	11.3 (3)
O30—C30—C31—C32	−16.1 (5)	C30^i—O30^i—C20—O20	11.7 (3)

Symmetry code: (i) −x+1, y−1/2, −z+1.