Isostructuralism in a series of methylester/methyl­amide derivatives of (R,R)-O,O′-dibenzoyl tartaric acid; inclusion properties and guest-dependent homeotypism of the crystals of (R,R)-O,O′-dibenzoyltartaric acid diamide

The compounds studied are methyl ester, amide and methylamide derivatives of (R,R)-O,O′-dibenzoyl tartaric acid. The molecules adopt the planar T conformation of the four-carbon chain with the terminal C=O bonds situated antiperiplanar with respect to the nearest C*—O bond. All investigated molecules occupy a twofold symmetry site in the crystal, including the mono(N-methylamide) monomethyl­ester which lacks the C₂ molecular symmetry. Connected with this is the static disorder in which the methylester and the N-methylamide groups replace each other and isostructuralism within the methylester/methylamide series. (R,R)-O,O′-Dibenzoyltartaric acid diamides [(R,R)-O,O′-dibenzoyl-2,3-dihydroxybutanediamides], both primary and secondary, form hydrogen-bond aggregation patterns typical for amides, despite the presence of other hydrogen-bond acceptors in the molecule. However, in primary amides such packing leads to the creation of homeotypic crystal structures in which structural voids are filled by cyclic solvent molecules (pyridine, 1,4-dioxane). The presence of polyamide ladders, consisting of `fused' hydrogen-bond rings, seems to be responsible for the low solubility and high melting point of these substances.

Computing details

Data collection: Kuma KM-4 Software (Kuma Diffraction, 1991) for bn11+1,4-dioxane, BN11+pyridine; SYNTEX Operation Manual for BN22, BOM; Kuma KM4CCD software (Kuma Diffraction, 1999) for BOM2. Cell refinement: Kuma KM-4 Software (Kuma Diffraction, 1991) for bn11+1,4-dioxane, BN11+pyridine; SYNTEX XTL Operation Manual for BN22, BOM; Kuma KM4CCD software for BOM2. Data reduction: Kuma KM-4 Software (Kuma Diffraction, 1991) for bn11+1,4-dioxane, BN11+pyridine; PRARA for BN22, BOM; Kuma KM4CCD software for BOM2. 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).

(bn11+1,4-dioxane) (R,R)-(-)-O,O'-Dibenzoyltartaric acid diamide

Crystal data

(C18H16N2O6)·(C4H8O2)	Dx = 1.345 Mg m^−3
Mr = 444.43	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, C2221	Cell parameters from 51 reflections
a = 5.253 (1) Å	θ = 12.2–23.6°
b = 26.748 (5) Å	µ = 0.87 mm^−1
c = 15.621 (3) Å	T = 293 K
V = 2194.9 (7) Å^3	Plate, colourless
Z = 4	0.40 × 0.30 × 0.05 mm
F(000) = 936

Data collection

KM-4 four circle diffractometer	Rint = 0.022
Radiation source: fine-focus sealed tube	θmax = 65.2°, θmin = 3.3°
Graphite monochromator	h = −5→5
Θ–2Θ scans	k = 0→31
1886 measured reflections	l = 0→18
1795 independent reflections	2 standard reflections every 100 reflections
1410 reflections with I > 2σ(I)	intensity decay: 2.2%

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)] = 0.049	w = 1/[σ^2(Fo^2) + (0.0893P)^2 + 0.2101P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.139	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.24 e Å^−3
1795 reflections	Δρmin = −0.18 e Å^−3
173 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
12 restraints	Extinction coefficient: 0.0020 (4)
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: −0.3 (4) The absolute structure of the crystals was assumed from the known absolute configuration of the reagents used in the synthesis

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	−0.4972 (6)	−0.47885 (10)	−0.38232 (15)	0.0436 (6)
C2	−0.4982 (6)	−0.47439 (10)	−0.47926 (15)	0.0436 (6)
H2	−0.3459	−0.4573	−0.4967	0.052*
C20	−0.6950 (6)	−0.39667 (12)	−0.50720 (18)	0.0557 (8)
C21	−0.8907 (7)	−0.37150 (12)	−0.5589 (2)	0.0602 (8)
C22	−0.9096 (10)	−0.31990 (15)	−0.5519 (3)	0.0919 (13)
H22	−0.7978	−0.3017	−0.5145	0.110*
C23	−1.0870 (12)	−0.2949 (2)	−0.6004 (4)	0.117 (2)
H23	−1.1005	−0.2591	−0.5983	0.140*
C24	−1.2411 (12)	−0.3205 (3)	−0.6551 (4)	0.123 (2)
H24	−1.3681	−0.3023	−0.6865	0.148*
C25	−1.2257 (10)	−0.3717 (2)	−0.6633 (3)	0.1028 (16)
H25	−1.3410	−0.3895	−0.6999	0.123*
C26	−1.0447 (7)	−0.39718 (15)	−0.6148 (2)	0.0681 (10)
H26	−1.0214	−0.4325	−0.6218	0.082*
N1	−0.7154 (5)	−0.47510 (10)	−0.34160 (13)	0.0537 (7)
H12	−0.8600	−0.4692	−0.3708	0.064*
H11	−0.7192	−0.4778	−0.2842	0.064*
O1	−0.2913 (4)	−0.48699 (9)	−0.34697 (12)	0.0554 (6)
O2	−0.7126 (4)	−0.44750 (7)	−0.51260 (10)	0.0479 (5)
O20	−0.5344 (6)	−0.37677 (9)	−0.46477 (17)	0.0793 (8)
O1S	−1.048 (3)	−0.3842 (2)	−0.2478 (10)	0.145 (5)	0.50
C2S	−1.100 (4)	−0.3547 (4)	−0.3198 (7)	0.126 (6)	0.50
H2S1	−1.2468	−0.3672	−0.3497	0.151*	0.50
H2S2	−0.9573	−0.3563	−0.3579	0.151*	0.50
C3S	−1.146 (4)	−0.3013 (4)	−0.2936 (11)	0.191 (14)	0.50
H3S1	−1.2948	−0.2982	−0.2582	0.229*	0.50
H3S2	−1.1701	−0.2809	−0.3437	0.229*	0.50
O4S	−0.932 (2)	−0.2837 (2)	−0.2486 (11)	0.152 (6)	0.50
C5S	−0.877 (4)	−0.3135 (4)	−0.1773 (8)	0.140 (9)	0.50
H5S1	−1.0242	−0.3118	−0.1411	0.167*	0.50
H5S2	−0.7330	−0.3014	−0.1456	0.167*	0.50
C6S	−0.828 (4)	−0.3668 (4)	−0.2053 (11)	0.176 (13)	0.50
H6S1	−0.6781	−0.3676	−0.2403	0.212*	0.50
H6S2	−0.8003	−0.3878	−0.1563	0.212*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0418 (14)	0.0566 (15)	0.0324 (11)	−0.0003 (14)	−0.0027 (13)	−0.0041 (11)
C2	0.0374 (13)	0.0616 (16)	0.0317 (11)	0.0014 (15)	−0.0035 (12)	0.0004 (11)
C20	0.0594 (19)	0.0613 (18)	0.0463 (15)	0.0009 (15)	−0.0017 (16)	−0.0004 (13)
C21	0.0633 (19)	0.0619 (19)	0.0555 (18)	0.0072 (15)	0.0073 (15)	0.0104 (15)
C22	0.104 (3)	0.070 (2)	0.102 (3)	0.018 (2)	0.006 (3)	0.009 (2)
C23	0.130 (5)	0.084 (3)	0.137 (5)	0.042 (3)	0.015 (4)	0.032 (3)
C24	0.118 (5)	0.125 (5)	0.127 (5)	0.049 (4)	0.002 (4)	0.052 (4)
C25	0.089 (3)	0.134 (5)	0.085 (3)	0.032 (3)	−0.020 (3)	0.021 (3)
C26	0.061 (2)	0.089 (2)	0.0537 (18)	0.0119 (17)	−0.0043 (16)	0.0143 (17)
N1	0.0407 (14)	0.0884 (18)	0.0322 (10)	0.0051 (13)	−0.0017 (10)	−0.0012 (11)
O1	0.0409 (11)	0.0895 (16)	0.0359 (9)	0.0044 (10)	−0.0062 (9)	−0.0035 (9)
O2	0.0493 (11)	0.0561 (11)	0.0383 (9)	0.0029 (9)	−0.0066 (9)	0.0014 (8)
O20	0.0846 (18)	0.0694 (15)	0.0838 (16)	−0.0090 (13)	−0.0199 (15)	−0.0105 (12)
O1S	0.186 (15)	0.093 (4)	0.156 (6)	−0.072 (9)	−0.030 (9)	0.036 (10)
C2S	0.201 (16)	0.107 (11)	0.070 (6)	−0.064 (11)	−0.041 (7)	0.009 (7)
C3S	0.27 (3)	0.085 (10)	0.22 (3)	0.057 (14)	−0.13 (2)	−0.047 (13)
O4S	0.158 (17)	0.074 (5)	0.222 (10)	−0.012 (5)	−0.005 (12)	0.047 (8)
C5S	0.27 (2)	0.067 (8)	0.078 (7)	−0.036 (11)	−0.018 (9)	0.000 (7)
C6S	0.27 (3)	0.093 (9)	0.167 (18)	0.004 (13)	−0.121 (19)	−0.050 (10)

Geometric parameters (Å, º)

C1—O1	1.234 (3)	C25—H25	0.9600
C1—N1	1.315 (4)	C26—H26	0.9600
C1—C2	1.519 (3)	N1—H12	0.9000
C2—O2	1.434 (3)	N1—H11	0.9000
C2—C2^i	1.515 (5)	O1S—C2S	1.402 (9)
C2—H2	0.9600	O1S—C6S	1.409 (10)
C20—O20	1.198 (4)	C2S—C3S	1.506 (9)
C20—O2	1.365 (4)	C2S—H2S1	0.9600
C20—C21	1.470 (5)	C2S—H2S2	0.9600
C21—C26	1.375 (5)	C3S—O4S	1.410 (10)
C21—C22	1.388 (5)	C3S—H3S1	0.9600
C22—C23	1.375 (7)	C3S—H3S2	0.9600
C22—H22	0.9601	O4S—C5S	1.399 (9)
C23—C24	1.362 (8)	C5S—C6S	1.514 (9)
C23—H23	0.9600	C5S—H5S1	0.9600
C24—C25	1.378 (9)	C5S—H5S2	0.9600
C24—H24	0.9600	C6S—H6S1	0.9600
C25—C26	1.394 (5)	C6S—H6S2	0.9600
O1—C1—N1	124.1 (2)	O4S^ii—C3S—C2S	128.0 (13)
O1—C1—C2	117.6 (2)	O4S—C3S—C2S	108.9 (9)
N1—C1—C2	118.2 (2)	C5S^ii—C3S—C6S^ii	55.8 (19)
O2—C2—C2^i	107.35 (17)	O4S^ii—C3S—C6S^ii	123.9 (16)
O2—C2—C1	113.8 (2)	O4S—C3S—C6S^ii	113.4 (10)
C2^i—C2—C1	110.8 (3)	C2S—C3S—C6S^ii	20.5 (11)
O2—C2—H2	108.3	C5S^ii—C3S—H3S1	132.8
C2^i—C2—H2	108.0	O4S^ii—C3S—H3S1	84.4
C1—C2—H2	108.5	O4S—C3S—H3S1	109.5
O20—C20—O2	121.6 (3)	C2S—C3S—H3S1	111.7
O20—C20—C21	126.4 (3)	C6S^ii—C3S—H3S1	91.7
O2—C20—C21	112.0 (3)	C5S^ii—C3S—H3S2	72.9
C26—C21—C22	120.3 (4)	O4S^ii—C3S—H3S2	110.9
C26—C21—C20	122.1 (3)	O4S—C3S—H3S2	108.7
C22—C21—C20	117.5 (4)	C2S—C3S—H3S2	109.7
C23—C22—C21	119.3 (5)	C6S^ii—C3S—H3S2	123.1
C23—C22—H22	120.2	H3S1—C3S—H3S2	108.4
C21—C22—H22	120.5	O4S^ii—O4S—C3S^ii	120 (3)
C24—C23—C22	120.2 (5)	O4S^ii—O4S—C5S	105 (3)
C24—C23—H23	118.6	C3S^ii—O4S—C5S	15.0 (19)
C22—C23—H23	121.1	O4S^ii—O4S—C3S	34.0 (17)
C23—C24—C25	121.6 (5)	C3S^ii—O4S—C3S	123.4 (13)
C23—C24—H24	118.6	C5S—O4S—C3S	111.8 (9)
C25—C24—H24	119.8	O4S^ii—O4S—C5S^ii	52 (2)
C24—C25—C26	118.4 (5)	C3S^ii—O4S—C5S^ii	120.7 (9)
C24—C25—H25	120.8	C5S—O4S—C5S^ii	112.9 (8)
C26—C25—H25	120.8	C3S—O4S—C5S^ii	17.5 (12)
C21—C26—C25	120.2 (4)	C3S^ii—C5S—C2S^ii	124 (3)
C21—C26—H26	119.3	C3S^ii—C5S—O4S	24 (3)
C25—C26—H26	120.4	C2S^ii—C5S—O4S	120.8 (11)
C1—N1—H12	120.3	C3S^ii—C5S—C6S	106 (3)
C1—N1—H11	119.7	C2S^ii—C5S—C6S	21.6 (15)
H12—N1—H11	120.0	O4S—C5S—C6S	110.0 (8)
C20—O2—C2	115.1 (2)	C3S^ii—C5S—O4S^ii	48 (3)
O1S^ii—O1S—C6S^ii	120 (4)	C2S^ii—C5S—O4S^ii	111.6 (15)
O1S^ii—O1S—C2S	95 (3)	O4S—C5S—O4S^ii	23.7 (10)
C6S^ii—O1S—C2S	25.6 (15)	C6S—C5S—O4S^ii	109.9 (7)
O1S^ii—O1S—C6S	42 (3)	C3S^ii—C5S—H5S1	127.6
C6S^ii—O1S—C6S	132.0 (11)	C2S^ii—C5S—H5S1	89.1
C2S—O1S—C6S	110.7 (9)	O4S—C5S—H5S1	106.0
O1S^ii—O1S—C2S^ii	66 (3)	C6S—C5S—H5S1	110.6
C6S^ii—O1S—C2S^ii	123.5 (8)	O4S^ii—C5S—H5S1	84.4
C2S—O1S—C2S^ii	111.3 (8)	C3S^ii—C5S—H5S2	92.7
C6S—O1S—C2S^ii	24.4 (12)	C2S^ii—C5S—H5S2	116.2
C6S^ii—C2S—C5S^ii	118 (3)	O4S—C5S—H5S2	112.3
C6S^ii—C2S—O1S	48 (2)	C6S—C5S—H5S2	109.6
C5S^ii—C2S—O1S	127.8 (11)	O4S^ii—C5S—H5S2	130.3
C6S^ii—C2S—C3S	103 (3)	H5S1—C5S—H5S2	108.3
C5S^ii—C2S—C3S	18.4 (12)	C2S^ii—C6S—O1S^ii	107 (4)
O1S—C2S—C3S	110.3 (9)	C2S^ii—C6S—O1S	89 (3)
C6S^ii—C2S—O1S^ii	67 (2)	O1S^ii—C6S—O1S	18.2 (17)
C5S^ii—C2S—O1S^ii	126.5 (15)	C2S^ii—C6S—C5S	40 (2)
O1S—C2S—O1S^ii	19.3 (14)	O1S^ii—C6S—C5S	119.8 (11)
C3S—C2S—O1S^ii	112.6 (7)	O1S—C6S—C5S	108.0 (9)
C6S^ii—C2S—H2S1	69.4	C2S^ii—C6S—C3S^ii	56.5 (18)
C5S^ii—C2S—H2S1	103.8	O1S^ii—C6S—C3S^ii	112.0 (13)
O1S—C2S—H2S1	110.6	O1S—C6S—C3S^ii	105.2 (10)
C3S—C2S—H2S1	109.5	C5S—C6S—C3S^ii	18.2 (9)
O1S^ii—C2S—H2S1	124.3	C2S^ii—C6S—H6S1	148.2
C6S^ii—C2S—H2S2	145.5	O1S^ii—C6S—H6S1	95.7
C5S^ii—C2S—H2S2	96.1	O1S—C6S—H6S1	113.5
O1S—C2S—H2S2	108.6	C5S—C6S—H6S1	108.8
C3S—C2S—H2S2	109.8	C3S^ii—C6S—H6S1	94.4
O1S^ii—C2S—H2S2	90.3	C2S^ii—C6S—H6S2	84.1
H2S1—C2S—H2S2	108.0	O1S^ii—C6S—H6S2	112.5
C5S^ii—C3S—O4S^ii	141 (5)	O1S—C6S—H6S2	108.0
C5S^ii—C3S—O4S	115 (4)	C5S—C6S—H6S2	110.2
O4S^ii—C3S—O4S	26.3 (16)	C3S^ii—C6S—H6S2	126.9
C5S^ii—C3S—C2S	37.6 (17)	H6S1—C6S—H6S2	108.4
O1—C1—C2—O2	−158.1 (2)	O4S^ii—C3S—O4S—C3S^ii	95 (4)
N1—C1—C2—O2	23.6 (4)	C2S—C3S—O4S—C3S^ii	−46.3 (18)
O1—C1—C2—C2^i	80.8 (3)	C6S^ii—C3S—O4S—C3S^ii	−25 (2)
N1—C1—C2—C2^i	−97.5 (3)	C5S^ii—C3S—O4S—C5S	−97 (3)
O20—C20—C21—C26	170.8 (3)	O4S^ii—C3S—O4S—C5S	84 (3)
O2—C20—C21—C26	−8.8 (4)	C2S—C3S—O4S—C5S	−57 (2)
O20—C20—C21—C22	−6.8 (5)	C6S^ii—C3S—O4S—C5S	−36 (2)
O2—C20—C21—C22	173.6 (3)	O4S^ii—C3S—O4S—C5S^ii	−179 (4)
C26—C21—C22—C23	1.1 (6)	C2S—C3S—O4S—C5S^ii	40.1 (18)
C20—C21—C22—C23	178.7 (4)	C6S^ii—C3S—O4S—C5S^ii	62 (2)
C21—C22—C23—C24	−0.4 (8)	O4S^ii—O4S—C5S—C3S^ii	178 (5)
C22—C23—C24—C25	0.3 (9)	C3S—O4S—C5S—C3S^ii	143 (4)
C23—C24—C25—C26	−0.8 (8)	C5S^ii—O4S—C5S—C3S^ii	124 (5)
C22—C21—C26—C25	−1.7 (6)	O4S^ii—O4S—C5S—C2S^ii	73 (3)
C20—C21—C26—C25	−179.2 (4)	C3S^ii—O4S—C5S—C2S^ii	−105 (5)
C24—C25—C26—C21	1.5 (7)	C3S—O4S—C5S—C2S^ii	38 (3)
O20—C20—O2—C2	−12.3 (4)	C5S^ii—O4S—C5S—C2S^ii	19 (2)
C21—C20—O2—C2	167.3 (2)	O4S^ii—O4S—C5S—C6S	94 (2)
C2^i—C2—O2—C20	−157.8 (2)	C3S^ii—O4S—C5S—C6S	−84 (5)
C1—C2—O2—C20	79.2 (3)	C3S—O4S—C5S—C6S	58.9 (18)
O1S^ii—O1S—C2S—C6S^ii	170 (3)	C5S^ii—O4S—C5S—C6S	39.9 (13)
C6S—O1S—C2S—C6S^ii	−150 (2)	C3S^ii—O4S—C5S—O4S^ii	−178 (5)
C2S^ii—O1S—C2S—C6S^ii	−124 (3)	C3S—O4S—C5S—O4S^ii	−35.1 (13)
O1S^ii—O1S—C2S—C5S^ii	−94 (4)	C5S^ii—O4S—C5S—O4S^ii	−54.0 (14)
C6S^ii—O1S—C2S—C5S^ii	96 (4)	O1S^ii—O1S—C6S—C2S^ii	169 (3)
C6S—O1S—C2S—C5S^ii	−54 (3)	C6S^ii—O1S—C6S—C2S^ii	79 (2)
C2S^ii—O1S—C2S—C5S^ii	−28 (2)	C2S—O1S—C6S—C2S^ii	96 (2)
O1S^ii—O1S—C2S—C3S	−100 (2)	C6S^ii—O1S—C6S—O1S^ii	−90 (4)
C6S^ii—O1S—C2S—C3S	89 (3)	C2S—O1S—C6S—O1S^ii	−73 (3)
C6S—O1S—C2S—C3S	−60.5 (17)	C2S^ii—O1S—C6S—O1S^ii	−169 (3)
C2S^ii—O1S—C2S—C3S	−34.4 (14)	O1S^ii—O1S—C6S—C5S	134 (3)
C6S^ii—O1S—C2S—O1S^ii	−170 (3)	C6S^ii—O1S—C6S—C5S	43 (2)
C6S—O1S—C2S—O1S^ii	39.8 (17)	C2S—O1S—C6S—C5S	60.3 (17)
C2S^ii—O1S—C2S—O1S^ii	65.9 (19)	C2S^ii—O1S—C6S—C5S	−35.9 (14)
C6S^ii—C2S—C3S—C5S^ii	−147 (7)	O1S^ii—O1S—C6S—C3S^ii	115 (3)
O1S—C2S—C3S—C5S^ii	163 (5)	C6S^ii—O1S—C6S—C3S^ii	25 (2)
O1S^ii—C2S—C3S—C5S^ii	142 (6)	C2S—O1S—C6S—C3S^ii	42 (2)
C6S^ii—C2S—C3S—O4S^ii	86 (4)	C2S^ii—O1S—C6S—C3S^ii	−54.7 (16)
C5S^ii—C2S—C3S—O4S^ii	−127 (7)	C3S^ii—C5S—C6S—C2S^ii	−149 (6)
O1S—C2S—C3S—O4S^ii	36 (3)	O4S—C5S—C6S—C2S^ii	−124 (4)
O1S^ii—C2S—C3S—O4S^ii	16 (4)	O4S^ii—C5S—C6S—C2S^ii	−99 (4)
C6S^ii—C2S—C3S—O4S	107 (3)	C3S^ii—C5S—C6S—O1S^ii	−69 (4)
C5S^ii—C2S—C3S—O4S	−106 (6)	C2S^ii—C5S—C6S—O1S^ii	80 (4)
O1S—C2S—C3S—O4S	57.1 (18)	O4S—C5S—C6S—O1S^ii	−44 (3)
O1S^ii—C2S—C3S—O4S	36 (2)	O4S^ii—C5S—C6S—O1S^ii	−19 (3)
C5S^ii—C2S—C3S—C6S^ii	147 (7)	C3S^ii—C5S—C6S—O1S	−84 (4)
O1S—C2S—C3S—C6S^ii	−50 (2)	C2S^ii—C5S—C6S—O1S	65 (4)
O1S^ii—C2S—C3S—C6S^ii	−70 (2)	O4S—C5S—C6S—O1S	−59.0 (16)
C5S^ii—C3S—O4S—O4S^ii	179 (4)	O4S^ii—C5S—C6S—O1S	−33.7 (18)
C2S—C3S—O4S—O4S^ii	−141 (3)	C2S^ii—C5S—C6S—C3S^ii	149 (6)
C6S^ii—C3S—O4S—O4S^ii	−120 (3)	O4S—C5S—C6S—C3S^ii	25 (3)
C5S^ii—C3S—O4S—C3S^ii	−86 (2)	O4S^ii—C5S—C6S—C3S^ii	50 (3)

Symmetry codes: (i) x, −y−1, −z−1; (ii) −x−2, y, −z−1/2.

(BN22) (R,R)-(-)-O,O'-Dibenzoyltartaric acid N,N'-dimethyldiamide

Crystal data

C20H20N2O6	Dx = 1.341 Mg m^−3
Mr = 384.38	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P21212	Cell parameters from 15 reflections
a = 10.282 (2) Å	θ = 10.5–14.2°
b = 18.024 (4) Å	µ = 0.10 mm^−1
c = 5.136 (1) Å	T = 293 K
V = 951.8 (3) Å^3	Plate, colourless
Z = 2	0.50 × 0.40 × 0.30 mm
F(000) = 404

Data collection

Syntex P21 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 26.1°, θmin = 2.3°
Graphite monochromator	h = −12→0
Θ–2Θ scans	k = −22→0
1097 measured reflections	l = −6→0
1097 independent reflections	3 standard reflections every 100 reflections
798 reflections with I > 2σ(I)	intensity decay: 3.6%

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)] = 0.045	w = 1/[σ^2(Fo^2) + (0.0827P)^2 + 0.1003P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.135	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.16 e Å^−3
1097 reflections	Δρmin = −0.17 e Å^−3
128 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.029 (8)
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: The absolute structure of the crystals was assumed from the known absolute configuration of the reagents used in the synthesis

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	0.3606 (3)	0.42810 (18)	−0.0754 (6)	0.0419 (8)
C2	0.5001 (3)	0.45734 (18)	−0.0704 (6)	0.0416 (8)
H2	0.5438	0.4407	−0.2250	0.050*
C10	0.1725 (4)	0.3870 (2)	0.1701 (9)	0.0623 (11)
H101	0.1352	0.4005	0.3348	0.075*
H102	0.1684	0.3341	0.1497	0.075*
H103	0.1226	0.4091	0.0324	0.075*
C20	0.6250 (3)	0.36326 (18)	0.1324 (8)	0.0443 (8)
C21	0.7272 (3)	0.34952 (18)	0.3265 (7)	0.0435 (8)
C22	0.7804 (4)	0.2781 (2)	0.3396 (9)	0.0626 (11)
H22	0.7478	0.2398	0.2273	0.075*
C23	0.8773 (5)	0.2626 (2)	0.5135 (10)	0.0700 (12)
H23	0.9151	0.2139	0.5167	0.084*
C24	0.9225 (4)	0.3171 (2)	0.6774 (10)	0.0693 (12)
H24	0.9879	0.3052	0.8042	0.083*
C25	0.8730 (4)	0.3875 (2)	0.6639 (9)	0.0653 (11)
H25	0.9040	0.4254	0.7798	0.078*
C26	0.7755 (3)	0.4041 (2)	0.4874 (8)	0.0499 (9)
H26	0.7434	0.4539	0.4719	0.060*
N1	0.3054 (3)	0.41111 (16)	0.1495 (6)	0.0474 (8)
H1	0.3536	0.4144	0.2952	0.057*
O1	0.3066 (3)	0.42443 (16)	−0.2890 (5)	0.0568 (7)
O2	0.5755 (2)	0.43427 (12)	0.1509 (4)	0.0435 (6)
O20	0.5853 (3)	0.32042 (14)	−0.0292 (5)	0.0593 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0493 (18)	0.0403 (17)	0.0361 (17)	0.0013 (15)	−0.0053 (16)	−0.0005 (16)
C2	0.0441 (16)	0.0468 (18)	0.0339 (15)	0.0005 (16)	−0.0013 (16)	−0.0020 (15)
C10	0.052 (2)	0.083 (3)	0.052 (2)	−0.015 (2)	0.002 (2)	−0.005 (2)
C20	0.0439 (17)	0.0403 (18)	0.0486 (19)	−0.0023 (15)	0.0031 (18)	0.0002 (17)
C21	0.0442 (17)	0.0410 (16)	0.0452 (18)	−0.0018 (14)	0.0011 (17)	0.0017 (15)
C22	0.068 (2)	0.048 (2)	0.072 (3)	−0.0006 (18)	−0.015 (2)	0.003 (2)
C23	0.070 (2)	0.054 (2)	0.086 (3)	0.010 (2)	−0.020 (3)	0.013 (2)
C24	0.056 (2)	0.072 (3)	0.081 (3)	0.005 (2)	−0.025 (2)	0.012 (3)
C25	0.058 (2)	0.071 (3)	0.067 (3)	−0.005 (2)	−0.020 (2)	−0.008 (2)
C26	0.0469 (19)	0.0481 (19)	0.055 (2)	0.0001 (16)	−0.0025 (17)	0.0023 (17)
N1	0.0460 (16)	0.0629 (18)	0.0333 (14)	−0.0108 (14)	−0.0049 (14)	0.0007 (14)
O1	0.0626 (15)	0.0703 (17)	0.0375 (13)	−0.0079 (14)	−0.0114 (13)	0.0017 (12)
O2	0.0436 (12)	0.0447 (13)	0.0421 (12)	0.0019 (9)	−0.0080 (11)	−0.0039 (11)
O20	0.0688 (16)	0.0462 (13)	0.0628 (16)	0.0014 (12)	−0.0128 (15)	−0.0063 (13)

Geometric parameters (Å, º)

C1—O1	1.232 (4)	C21—C26	1.377 (5)
C1—N1	1.323 (5)	C21—C22	1.400 (5)
C1—C2	1.528 (5)	C22—C23	1.367 (6)
C2—O2	1.437 (4)	C22—H22	0.9600
C2—C2^i	1.538 (6)	C23—C24	1.374 (6)
C2—H2	0.9600	C23—H23	0.9600
C10—N1	1.438 (5)	C24—C25	1.370 (6)
C10—H101	0.9600	C24—H24	0.9600
C10—H102	0.9600	C25—C26	1.384 (5)
C10—H103	0.9600	C25—H25	0.9600
C20—O20	1.205 (4)	C26—H26	0.9600
C20—O2	1.381 (4)	N1—H1	0.9000
C20—C21	1.470 (5)
O1—C1—N1	124.9 (3)	C22—C21—C20	117.8 (3)
O1—C1—C2	117.2 (3)	C23—C22—C21	120.2 (4)
N1—C1—C2	117.9 (3)	C23—C22—H22	120.0
O2—C2—C1	114.8 (3)	C21—C22—H22	119.8
O2—C2—C2^i	106.9 (2)	C22—C23—C24	120.1 (4)
C1—C2—C2^i	110.1 (3)	C22—C23—H23	119.5
O2—C2—H2	108.1	C24—C23—H23	120.4
C1—C2—H2	108.6	C25—C24—C23	120.3 (4)
C2^i—C2—H2	108.2	C25—C24—H24	120.0
N1—C10—H101	111.6	C23—C24—H24	119.6
N1—C10—H102	109.5	C24—C25—C26	120.1 (4)
H101—C10—H102	109.3	C24—C25—H25	120.3
N1—C10—H103	109.1	C26—C25—H25	119.5
H101—C10—H103	109.3	C21—C26—C25	120.0 (3)
H102—C10—H103	107.9	C21—C26—H26	119.6
O20—C20—O2	121.1 (3)	C25—C26—H26	120.4
O20—C20—C21	127.0 (3)	C1—N1—C10	122.8 (3)
O2—C20—C21	111.9 (3)	C1—N1—H1	118.3
C26—C21—C22	119.1 (3)	C10—N1—H1	118.8
C26—C21—C20	123.0 (3)	C20—O2—C2	114.4 (3)
O1—C1—C2—O2	−156.5 (3)	C23—C24—C25—C26	1.0 (8)
N1—C1—C2—O2	25.8 (4)	C22—C21—C26—C25	−1.7 (6)
O1—C1—C2—C2^i	82.9 (3)	C20—C21—C26—C25	−179.2 (4)
N1—C1—C2—C2^i	−94.8 (3)	C24—C25—C26—C21	0.6 (7)
O20—C20—C21—C26	173.4 (4)	O1—C1—N1—C10	−1.0 (6)
O2—C20—C21—C26	−6.2 (5)	C2—C1—N1—C10	176.5 (3)
O20—C20—C21—C22	−4.1 (6)	O20—C20—O2—C2	−14.4 (5)
O2—C20—C21—C22	176.2 (3)	C21—C20—O2—C2	165.2 (3)
C26—C21—C22—C23	1.2 (6)	C1—C2—O2—C20	79.7 (3)
C20—C21—C22—C23	178.9 (4)	C2^i—C2—O2—C20	−157.9 (3)
C21—C22—C23—C24	0.3 (8)	C1—C2—C2^i—C1^i	−178.0 (4)
C22—C23—C24—C25	−1.5 (8)

Symmetry code: (i) −x+1, −y+1, z.

(BN11+pyridine) (R,R)-(-)-O,O'-Dibenzoyltartaric acid diamide

Crystal data

(C18H16N2O6)·(C5H5N)	F(000) = 912
Mr = 435.43	Dx = 1.290 Mg m^−3
Monoclinic, C2	Cu Kα radiation, λ = 1.54178 Å
a = 27.898 (6) Å	Cell parameters from 53 reflections
b = 5.145 (1) Å	θ = 12.0–25.0°
c = 15.648 (3) Å	µ = 0.79 mm^−1
β = 93.49 (3)°	T = 293 K
V = 2241.9 (8) Å^3	Needle, colourless
Z = 4	0.60 × 0.12 × 0.08 mm

Data collection

KM-4 four circle diffractometer	Rint = 0.043
Radiation source: fine-focus sealed tube	θmax = 64.8°, θmin = 2.8°
Graphite monochromator	h = −32→32
Θ–2Θ scans	k = −6→6
3629 measured reflections	l = 0→18
3559 independent reflections	2 standard reflections every 100 reflections
1994 reflections with I > 2σ(I)	intensity decay: 0.4%

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)] = 0.046	w = 1/[σ^2(Fo^2) + (0.0746P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.139	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.19 e Å^−3
3559 reflections	Δρmin = −0.17 e Å^−3
290 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0021 (2)
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: The absolute structure of the crystals was assumed from the known absolute configuration of the reagents used in the synthesis

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	−0.02098 (13)	0.1124 (8)	−0.61983 (19)	0.0430 (8)
O1	−0.01389 (11)	−0.0982 (5)	−0.65479 (14)	0.0541 (8)
N1	−0.02395 (12)	0.3368 (6)	−0.66063 (17)	0.0551 (9)
H12	−0.0281	0.4849	−0.6314	0.066*
H11	−0.0219	0.3416	−0.7178	0.066*
C2	−0.02465 (12)	0.1138 (8)	−0.52310 (19)	0.0446 (9)
H2	−0.0410	−0.0415	−0.5074	0.054*
O2	−0.05053 (10)	0.3339 (4)	−0.49221 (14)	0.0466 (7)
C20	−0.09909 (17)	0.3187 (9)	−0.5049 (2)	0.0566 (11)
O20	−0.11806 (12)	0.1580 (7)	−0.5522 (2)	0.0817 (10)
C21	−0.12418 (17)	0.5156 (9)	−0.4549 (3)	0.0624 (12)
C22	−0.1735 (2)	0.5421 (12)	−0.4699 (4)	0.104 (2)
H22	−0.1906	0.4391	−0.5128	0.125*
C23	−0.1980 (3)	0.7237 (18)	−0.4205 (6)	0.132 (3)
H23	−0.2321	0.7439	−0.4294	0.159*
C24	−0.1728 (3)	0.8684 (18)	−0.3612 (5)	0.134 (3)
H24	−0.1898	0.9907	−0.3279	0.160*
C25	−0.1246 (2)	0.8463 (13)	−0.3473 (4)	0.1010 (18)
H25	−0.1077	0.9558	−0.3059	0.121*
C26	−0.10014 (18)	0.6652 (9)	−0.3932 (3)	0.0704 (14)
H26	−0.0662	0.6438	−0.3818	0.085*
C1'	−0.48202 (14)	−0.3805 (8)	−0.1174 (2)	0.0464 (9)
O1'	−0.48756 (11)	−0.1655 (5)	−0.15282 (15)	0.0592 (8)
N1'	−0.48161 (12)	−0.6012 (6)	−0.15855 (17)	0.0539 (9)
H12'	−0.4777	−0.7512	−0.1293	0.065*
H11'	−0.4850	−0.6034	−0.2161	0.065*
C2'	−0.47600 (13)	−0.3829 (8)	−0.02025 (19)	0.0446 (9)
H2'	−0.4590	−0.2282	−0.0022	0.054*
O2'	−0.44940 (10)	−0.6045 (5)	0.01372 (13)	0.0480 (7)
C20'	−0.40117 (17)	−0.5972 (9)	0.0022 (2)	0.0577 (11)
O20'	−0.38439 (12)	−0.4391 (7)	−0.0440 (2)	0.0813 (10)
C21'	−0.37431 (18)	−0.7991 (8)	0.0517 (3)	0.0659 (13)
C22'	−0.3273 (2)	−0.8420 (12)	0.0343 (4)	0.0985 (18)
H22'	−0.3133	−0.7452	−0.0104	0.118*
C23'	−0.3007 (3)	−1.0255 (18)	0.0804 (6)	0.137 (3)
H23'	−0.2682	−1.0590	0.0670	0.164*
C24'	−0.3208 (4)	−1.1577 (17)	0.1456 (6)	0.138 (3)
H24'	−0.3017	−1.2814	0.1786	0.165*
C25'	−0.3674 (3)	−1.1160 (13)	0.1637 (4)	0.117 (2)
H25'	−0.3810	−1.2121	0.2089	0.140*
C26'	−0.39442 (19)	−0.9358 (9)	0.1166 (3)	0.0750 (14)
H26'	−0.4272	−0.9053	0.1294	0.090*
N1S	−0.2191 (2)	−0.3953 (16)	−0.7090 (5)	0.139 (2)
C2S	−0.1804 (3)	−0.2495 (14)	−0.6912 (4)	0.114 (2)
H2S	−0.1816	−0.1176	−0.6480	0.136*
C3S	−0.1398 (3)	−0.2811 (18)	−0.7319 (6)	0.129 (3)
H3S	−0.1126	−0.1705	−0.7193	0.155*
C4S	−0.1387 (3)	−0.4756 (18)	−0.7921 (5)	0.119 (2)
H4S	−0.1098	−0.5132	−0.8201	0.143*
C5S	−0.1783 (4)	−0.6102 (17)	−0.8095 (5)	0.125 (2)
H5S	−0.1797	−0.7390	−0.8540	0.150*
C6S	−0.2154 (3)	−0.5667 (17)	−0.7658 (6)	0.133 (3)
H6S	−0.2430	−0.6743	−0.7786	0.159*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.070 (3)	0.0305 (18)	0.0279 (15)	0.001 (2)	0.0020 (15)	0.0012 (19)
O1	0.102 (2)	0.0295 (14)	0.0316 (12)	0.0058 (15)	0.0064 (13)	−0.0039 (12)
N1	0.107 (3)	0.0305 (19)	0.0278 (15)	0.0047 (19)	0.0074 (16)	0.0007 (14)
C2	0.074 (3)	0.0292 (18)	0.0308 (17)	0.003 (2)	0.0073 (16)	−0.0041 (19)
O2	0.0612 (19)	0.0393 (15)	0.0398 (13)	0.0047 (14)	0.0067 (12)	−0.0064 (12)
C20	0.069 (3)	0.054 (3)	0.046 (2)	−0.007 (2)	0.001 (2)	0.003 (2)
O20	0.080 (2)	0.079 (3)	0.083 (2)	−0.012 (2)	−0.0134 (17)	−0.016 (2)
C21	0.062 (3)	0.065 (3)	0.061 (3)	0.005 (2)	0.013 (2)	0.005 (2)
C22	0.083 (4)	0.112 (5)	0.119 (5)	0.018 (4)	0.012 (4)	0.008 (4)
C23	0.085 (5)	0.159 (8)	0.156 (7)	0.050 (5)	0.033 (5)	0.013 (6)
C24	0.140 (7)	0.135 (7)	0.132 (6)	0.047 (6)	0.059 (5)	−0.002 (6)
C25	0.120 (5)	0.101 (4)	0.086 (4)	0.032 (4)	0.034 (3)	−0.014 (4)
C26	0.082 (3)	0.071 (4)	0.060 (3)	0.010 (3)	0.022 (2)	−0.007 (2)
C1'	0.079 (3)	0.0318 (19)	0.0288 (16)	0.001 (2)	0.0086 (16)	0.000 (2)
O1'	0.117 (3)	0.0274 (15)	0.0338 (12)	0.0048 (16)	0.0121 (14)	0.0058 (12)
N1'	0.106 (3)	0.0288 (18)	0.0275 (15)	0.001 (2)	0.0110 (16)	0.0024 (15)
C2'	0.073 (3)	0.0310 (18)	0.0298 (16)	0.001 (2)	0.0034 (16)	0.0024 (19)
O2'	0.0660 (19)	0.0421 (15)	0.0361 (12)	0.0045 (15)	0.0059 (12)	0.0065 (12)
C20'	0.074 (3)	0.055 (3)	0.044 (2)	−0.007 (3)	0.008 (2)	−0.004 (2)
O20'	0.091 (2)	0.078 (2)	0.077 (2)	−0.0161 (19)	0.0230 (18)	0.0104 (18)
C21'	0.072 (3)	0.055 (3)	0.069 (3)	0.002 (2)	−0.005 (3)	−0.015 (2)
C22'	0.079 (4)	0.092 (5)	0.125 (5)	0.008 (4)	0.008 (4)	−0.009 (4)
C23'	0.090 (5)	0.138 (7)	0.178 (8)	0.041 (5)	−0.023 (5)	−0.022 (6)
C24'	0.156 (8)	0.108 (6)	0.141 (7)	0.055 (6)	−0.057 (6)	−0.005 (5)
C25'	0.158 (6)	0.095 (5)	0.093 (4)	0.037 (5)	−0.021 (4)	0.024 (4)
C26'	0.100 (4)	0.064 (3)	0.060 (3)	0.015 (3)	−0.010 (3)	0.009 (2)
N1S	0.097 (4)	0.153 (6)	0.171 (6)	−0.008 (5)	0.045 (4)	−0.042 (5)
C2S	0.128 (6)	0.109 (5)	0.104 (5)	−0.014 (5)	0.008 (5)	−0.017 (4)
C3S	0.099 (6)	0.138 (7)	0.149 (7)	−0.045 (5)	−0.012 (5)	0.016 (6)
C4S	0.095 (6)	0.141 (7)	0.125 (6)	0.024 (5)	0.030 (5)	0.021 (5)
C5S	0.137 (7)	0.133 (6)	0.108 (5)	−0.004 (6)	0.019 (5)	−0.024 (5)
C6S	0.100 (5)	0.151 (7)	0.149 (7)	−0.038 (5)	0.019 (5)	−0.052 (6)

Geometric parameters (Å, º)

C1—O1	1.235 (5)	C2'—C2'^ii	1.516 (7)
C1—N1	1.319 (5)	C2'—H2'	0.9601
C1—C2	1.523 (4)	O2'—C20'	1.369 (5)
N1—H12	0.9000	C20'—O20'	1.202 (5)
N1—H11	0.9000	C20'—C21'	1.474 (6)
C2—O2	1.442 (4)	C21'—C22'	1.373 (7)
C2—C2^i	1.514 (7)	C21'—C26'	1.382 (6)
C2—H2	0.9600	C22'—C23'	1.377 (10)
O2—C20	1.359 (5)	C22'—H22'	0.9600
C20—O20	1.209 (5)	C23'—C24'	1.374 (11)
C20—C21	1.481 (6)	C23'—H23'	0.9601
C21—C26	1.378 (6)	C24'—C25'	1.365 (10)
C21—C22	1.387 (7)	C24'—H24'	0.9600
C22—C23	1.415 (10)	C25'—C26'	1.380 (7)
C22—H22	0.9600	C25'—H25'	0.9600
C23—C24	1.352 (10)	C26'—H26'	0.9599
C23—H23	0.9600	N1S—C6S	1.261 (9)
C24—C25	1.355 (9)	N1S—C2S	1.332 (8)
C24—H24	0.9600	C2S—C3S	1.342 (10)
C25—C26	1.381 (7)	C2S—H2S	0.9601
C25—H25	0.9600	C3S—C4S	1.376 (10)
C26—H26	0.9599	C3S—H3S	0.9600
C1'—O1'	1.243 (5)	C4S—C5S	1.320 (10)
C1'—N1'	1.306 (5)	C4S—H4S	0.9600
C1'—C2'	1.520 (4)	C5S—C6S	1.294 (9)
N1'—H12'	0.9000	C5S—H5S	0.9599
N1'—H11'	0.9000	C6S—H6S	0.9599
C2'—O2'	1.444 (4)
O1—C1—N1	124.1 (3)	C2'^ii—C2'—C1'	111.8 (4)
O1—C1—C2	117.8 (3)	O2'—C2'—H2'	108.2
N1—C1—C2	118.1 (3)	C2'^ii—C2'—H2'	108.1
C1—N1—H12	120.1	C1'—C2'—H2'	108.1
C1—N1—H11	119.9	C20'—O2'—C2'	114.6 (3)
H12—N1—H11	120.0	O20'—C20'—O2'	121.3 (4)
O2—C2—C2^i	107.4 (2)	O20'—C20'—C21'	126.1 (4)
O2—C2—C1	113.7 (3)	O2'—C20'—C21'	112.6 (4)
C2^i—C2—C1	111.1 (3)	C22'—C21'—C26'	120.0 (5)
O2—C2—H2	108.2	C22'—C21'—C20'	118.0 (5)
C2^i—C2—H2	108.1	C26'—C21'—C20'	122.0 (4)
C1—C2—H2	108.2	C21'—C22'—C23'	119.8 (7)
C20—O2—C2	114.9 (3)	C21'—C22'—H22'	119.8
O20—C20—O2	121.6 (4)	C23'—C22'—H22'	120.4
O20—C20—C21	125.9 (5)	C24'—C23'—C22'	119.9 (7)
O2—C20—C21	112.5 (4)	C24'—C23'—H23'	120.5
C26—C21—C22	119.9 (5)	C22'—C23'—H23'	119.7
C26—C21—C20	121.8 (4)	C25'—C24'—C23'	120.8 (7)
C22—C21—C20	118.3 (5)	C25'—C24'—H24'	119.8
C21—C22—C23	118.7 (7)	C23'—C24'—H24'	119.4
C21—C22—H22	120.6	C24'—C25'—C26'	119.4 (7)
C23—C22—H22	120.7	C24'—C25'—H25'	119.8
C24—C23—C22	119.4 (7)	C26'—C25'—H25'	120.8
C24—C23—H23	120.5	C25'—C26'—C21'	120.1 (6)
C22—C23—H23	120.0	C25'—C26'—H26'	119.6
C23—C24—C25	122.1 (7)	C21'—C26'—H26'	120.3
C23—C24—H24	118.8	C6S—N1S—C2S	116.2 (6)
C25—C24—H24	119.1	N1S—C2S—C3S	122.0 (7)
C24—C25—C26	119.4 (7)	N1S—C2S—H2S	118.8
C24—C25—H25	120.0	C3S—C2S—H2S	119.2
C26—C25—H25	120.6	C2S—C3S—C4S	117.9 (7)
C21—C26—C25	120.4 (5)	C2S—C3S—H3S	120.7
C21—C26—H26	119.9	C4S—C3S—H3S	121.4
C25—C26—H26	119.7	C5S—C4S—C3S	118.0 (8)
O1'—C1'—N1'	124.0 (3)	C5S—C4S—H4S	121.1
O1'—C1'—C2'	117.1 (3)	C3S—C4S—H4S	120.9
N1'—C1'—C2'	118.8 (3)	C6S—C5S—C4S	119.1 (8)
C1'—N1'—H12'	120.0	C6S—C5S—H5S	120.3
C1'—N1'—H11'	120.0	C4S—C5S—H5S	120.5
H12'—N1'—H11'	120.0	N1S—C6S—C5S	126.6 (8)
O2'—C2'—C2'^ii	107.1 (2)	N1S—C6S—H6S	116.8
O2'—C2'—C1'	113.4 (3)	C5S—C6S—H6S	116.5
O1—C1—C2—O2	−157.2 (3)	N1'—C1'—C2'—C2'^ii	−94.3 (3)
N1—C1—C2—O2	25.0 (5)	C2'^ii—C2'—O2'—C20'	−163.5 (3)
O1—C1—C2—C2^i	81.5 (3)	C1'—C2'—O2'—C20'	72.7 (4)
N1—C1—C2—C2^i	−96.3 (3)	C2'—O2'—C20'—O20'	−10.9 (5)
C2^i—C2—O2—C20	−159.7 (3)	C2'—O2'—C20'—C21'	169.0 (3)
C1—C2—O2—C20	76.9 (4)	O20'—C20'—C21'—C22'	−11.3 (7)
C2—O2—C20—O20	−13.1 (5)	O2'—C20'—C21'—C22'	168.7 (4)
C2—O2—C20—C21	166.6 (3)	O20'—C20'—C21'—C26'	165.9 (4)
O20—C20—C21—C26	170.1 (4)	O2'—C20'—C21'—C26'	−14.0 (6)
O2—C20—C21—C26	−9.6 (5)	C26'—C21'—C22'—C23'	1.4 (8)
O20—C20—C21—C22	−8.0 (7)	C20'—C21'—C22'—C23'	178.7 (5)
O2—C20—C21—C22	172.3 (4)	C21'—C22'—C23'—C24'	−2.4 (11)
C26—C21—C22—C23	−0.2 (8)	C22'—C23'—C24'—C25'	2.2 (13)
C20—C21—C22—C23	178.0 (5)	C23'—C24'—C25'—C26'	−1.0 (12)
C21—C22—C23—C24	0.9 (11)	C24'—C25'—C26'—C21'	0.0 (9)
C22—C23—C24—C25	0.2 (13)	C22'—C21'—C26'—C25'	−0.2 (7)
C23—C24—C25—C26	−2.0 (12)	C20'—C21'—C26'—C25'	−177.4 (5)
C22—C21—C26—C25	−1.6 (7)	C6S—N1S—C2S—C3S	0.5 (12)
C20—C21—C26—C25	−179.7 (5)	N1S—C2S—C3S—C4S	−1.6 (12)
C24—C25—C26—C21	2.6 (8)	C2S—C3S—C4S—C5S	3.6 (11)
O1'—C1'—C2'—O2'	−153.8 (3)	C3S—C4S—C5S—C6S	−4.6 (12)
N1'—C1'—C2'—O2'	26.9 (5)	C2S—N1S—C6S—C5S	−1.7 (15)
O1'—C1'—C2'—C2'^ii	85.0 (3)	C4S—C5S—C6S—N1S	3.8 (15)

Symmetry codes: (i) −x, y, −z−1; (ii) −x−1, y, −z.

(BOM) Dimethyl (R,R)-(-)-O,O'-Dibenzoyltartrate

Crystal data

C20H18O8	Dx = 1.357 Mg m^−3
Mr = 386.34	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P21212	Cell parameters from 15 reflections
a = 9.462 (1) Å	θ = 6–17°
b = 17.653 (3) Å	µ = 0.90 mm^−1
c = 5.662 (1) Å	T = 293 K
V = 945.7 (3) Å^3	Needle, colourless
Z = 2	0.50 × 0.40 × 0.30 mm
F(000) = 404

Data collection

Syntex P21 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 57.2°, θmin = 5.0°
Graphite monochromator	h = −10→0
Θ–2Θ scans	k = −19→0
783 measured reflections	l = −6→0
783 independent reflections	2 standard reflections every 100 reflections
758 reflections with I > 2σ(I)	intensity decay: 2.0%

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)] = 0.025	w = 1/[σ^2(Fo^2) + (0.0428P)^2 + 0.1101P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.072	(Δ/σ)max < 0.001
S = 1.15	Δρmax = 0.13 e Å^−3
783 reflections	Δρmin = −0.09 e Å^−3
129 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0191 (15)
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: −0.5 (4) The absolute structure of the crystals was assumed from the known absolute configuration of the reagents used in the synthesis

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	−0.1451 (2)	0.07481 (11)	0.5486 (4)	0.0464 (6)
C2	0.0031 (2)	0.04329 (11)	0.5787 (4)	0.0447 (5)
H2	0.0411	0.0608	0.7261	0.054*
C10	−0.3109 (3)	0.12559 (15)	0.2803 (6)	0.0705 (7)
H101	−0.3208	0.1749	0.3498	0.085*
H102	−0.3788	0.0912	0.3468	0.085*
H103	−0.3259	0.1282	0.1129	0.085*
C20	0.1433 (2)	0.13642 (11)	0.3870 (4)	0.0463 (6)
C21	0.2473 (2)	0.14897 (11)	0.1960 (4)	0.0466 (5)
C22	0.3102 (2)	0.21992 (13)	0.1790 (5)	0.0622 (7)
H22	0.2860	0.2589	0.2903	0.075*
C23	0.4046 (3)	0.23485 (14)	0.0014 (6)	0.0742 (8)
H23	0.4478	0.2840	−0.0080	0.089*
C24	0.4391 (3)	0.17942 (16)	−0.1592 (5)	0.0713 (8)
H24	0.5046	0.1908	−0.2837	0.086*
C25	0.3797 (3)	0.10802 (16)	−0.1405 (5)	0.0676 (7)
H25	0.4050	0.0693	−0.2516	0.081*
C26	0.2839 (2)	0.09287 (12)	0.0369 (4)	0.0560 (6)
H26	0.2426	0.0434	0.0504	0.067*
O1	−0.22873 (19)	0.07376 (10)	0.7075 (3)	0.0707 (5)
O2	0.09775 (14)	0.06332 (7)	0.3912 (3)	0.0485 (4)
O10	−0.16872 (17)	0.10013 (9)	0.3333 (3)	0.0555 (5)
O20	0.09983 (18)	0.18266 (8)	0.5249 (3)	0.0612 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0555 (13)	0.0354 (10)	0.0483 (13)	0.0013 (10)	0.0052 (12)	−0.0009 (10)
C2	0.0497 (11)	0.0373 (10)	0.0472 (10)	0.0000 (9)	0.0002 (12)	−0.0007 (10)
C10	0.0593 (14)	0.0777 (16)	0.0745 (17)	0.0188 (13)	−0.0074 (14)	0.0012 (16)
C20	0.0451 (11)	0.0325 (10)	0.0613 (13)	0.0001 (9)	−0.0061 (11)	0.0023 (11)
C21	0.0427 (11)	0.0394 (10)	0.0577 (12)	0.0001 (9)	−0.0082 (11)	0.0077 (10)
C22	0.0601 (13)	0.0458 (12)	0.0808 (17)	−0.0043 (11)	0.0049 (14)	0.0030 (12)
C23	0.0680 (16)	0.0562 (15)	0.0983 (19)	−0.0113 (12)	0.0118 (18)	0.0164 (16)
C24	0.0579 (14)	0.0834 (18)	0.0726 (16)	−0.0070 (13)	0.0050 (14)	0.0153 (17)
C25	0.0642 (15)	0.0767 (16)	0.0617 (15)	0.0002 (13)	0.0066 (14)	−0.0011 (14)
C26	0.0554 (12)	0.0490 (12)	0.0637 (14)	−0.0039 (10)	−0.0034 (13)	0.0015 (12)
O1	0.0707 (11)	0.0775 (11)	0.0638 (10)	0.0166 (10)	0.0211 (11)	0.0060 (9)
O2	0.0485 (8)	0.0345 (7)	0.0625 (9)	−0.0035 (6)	0.0085 (8)	−0.0012 (7)
O10	0.0499 (8)	0.0591 (9)	0.0574 (10)	0.0074 (7)	0.0013 (8)	0.0054 (8)
O20	0.0687 (10)	0.0396 (8)	0.0752 (10)	−0.0028 (7)	0.0090 (10)	−0.0082 (8)

Geometric parameters (Å, º)

C1—O1	1.198 (3)	C20—C21	1.479 (3)
C1—O10	1.318 (3)	C21—C26	1.383 (3)
C1—C2	1.518 (3)	C21—C22	1.390 (3)
C2—O2	1.434 (2)	C22—C23	1.371 (4)
C2—C2^i	1.530 (4)	C22—H22	0.9600
C2—H2	0.9600	C23—C24	1.375 (4)
C10—O10	1.450 (3)	C23—H23	0.9600
C10—H101	0.9600	C24—C25	1.384 (4)
C10—H102	0.9600	C24—H24	0.9600
C10—H103	0.9600	C25—C26	1.379 (3)
C20—O20	1.202 (3)	C25—H25	0.9600
C20—O2	1.361 (2)	C26—H26	0.9600
O1—C1—O10	126.0 (2)	C26—C21—C20	122.39 (19)
O1—C1—C2	121.3 (2)	C22—C21—C20	118.1 (2)
O10—C1—C2	112.6 (2)	C23—C22—C21	120.2 (2)
O2—C2—C1	113.81 (16)	C23—C22—H22	119.9
O2—C2—C2^i	105.67 (15)	C21—C22—H22	119.8
C1—C2—C2^i	109.4 (2)	C22—C23—C24	120.2 (2)
O2—C2—H2	109.3	C22—C23—H23	119.5
C1—C2—H2	109.0	C24—C23—H23	120.3
C2^i—C2—H2	109.6	C23—C24—C25	120.1 (3)
O10—C10—H101	106.7	C23—C24—H24	119.3
O10—C10—H102	110.1	C25—C24—H24	120.6
H101—C10—H102	110.3	C26—C25—C24	119.9 (3)
O10—C10—H103	110.9	C26—C25—H25	120.2
H101—C10—H103	110.3	C24—C25—H25	119.9
H102—C10—H103	108.5	C25—C26—C21	120.0 (2)
O20—C20—O2	121.6 (2)	C25—C26—H26	120.2
O20—C20—C21	126.94 (18)	C21—C26—H26	119.8
O2—C20—C21	111.45 (18)	C20—O2—C2	116.40 (16)
C26—C21—C22	119.5 (2)	C1—O10—C10	117.0 (2)
O1—C1—C2—O2	−167.41 (19)	C22—C23—C24—C25	−0.7 (4)
O10—C1—C2—O2	14.3 (2)	C23—C24—C25—C26	1.2 (4)
O1—C1—C2—C2^i	74.7 (2)	C24—C25—C26—C21	−0.1 (4)
O10—C1—C2—C2^i	−103.62 (15)	C22—C21—C26—C25	−1.5 (3)
O20—C20—C21—C26	−175.9 (2)	C20—C21—C26—C25	178.9 (2)
O2—C20—C21—C26	3.6 (3)	O20—C20—O2—C2	−4.2 (3)
O20—C20—C21—C22	4.5 (3)	C21—C20—O2—C2	176.23 (16)
O2—C20—C21—C22	−176.02 (19)	C1—C2—O2—C20	73.2 (2)
C26—C21—C22—C23	1.9 (4)	C2^i—C2—O2—C20	−166.79 (18)
C20—C21—C22—C23	−178.4 (2)	O1—C1—O10—C10	−3.3 (3)
C21—C22—C23—C24	−0.8 (4)	C2—C1—O10—C10	174.96 (18)

Symmetry code: (i) −x, −y, z.

(BOM2) (R,R)-(-)-O,O'-Dibenzoyltartaric acid mono(N-methylamide) monomethylester

Crystal data

C20H19NO7	F(000) = 404
Mr = 385.36	Dx = 1.383 Mg m^−3
Orthorhombic, P21212	Mo Kα radiation, λ = 0.71073 Å
a = 9.898 (2) Å	µ = 0.11 mm^−1
b = 17.756 (4) Å	T = 160 K
c = 5.264 (1) Å	Needle, colourless
V = 925.1 (3) Å^3	0.70 × 0.15 × 0.15 mm
Z = 2

Data collection

Kuma KM4CCD κ-geometry diffractometer	966 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.059
Graphite monochromator	θmax = 25.0°, θmin = 4.3°
ω scans	h = −11→11
3976 measured reflections	k = −21→21
976 independent reflections	l = −6→3

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)] = 0.083	w = 1/[σ^2(Fo^2) + (0.P)^2 + 3.2945P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.168	(Δ/σ)max < 0.001
S = 1.14	Δρmax = 0.30 e Å^−3
976 reflections	Δρmin = −0.28 e Å^−3
128 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.014 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map	Absolute structure parameter: The absolute structure of the crystals was assumed from the known absolute configuration of the reagents used in the synthesis

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.

Static disorder in which the methylester and the N-methylamide groups replace each other.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	−1.1398 (7)	−0.4266 (3)	0.0565 (14)	0.0389 (17)
C2	−0.9987 (7)	−0.4568 (3)	0.0749 (12)	0.0318 (14)
H2	−0.9586	−0.4399	0.2309	0.038*
C10	−1.3173 (8)	−0.3773 (4)	−0.209 (2)	0.067 (3)
H101	−1.3280	−0.3261	−0.1547	0.081*
H102	−1.3412	−0.3815	−0.3856	0.081*
H103	−1.3766	−0.4093	−0.1135	0.081*
C20	−0.8620 (6)	−0.3630 (3)	−0.1203 (13)	0.0320 (15)
C21	−0.7557 (6)	−0.3498 (3)	−0.3145 (13)	0.0297 (14)
C22	−0.6997 (6)	−0.2791 (3)	−0.3252 (15)	0.0382 (16)
H22	−0.7276	−0.2406	−0.2085	0.046*
C23	−0.6012 (7)	−0.2639 (4)	−0.5058 (15)	0.0432 (17)
H23	−0.5614	−0.2147	−0.5137	0.052*
C24	−0.5604 (6)	−0.3196 (4)	−0.6727 (15)	0.0435 (17)
H24	−0.4936	−0.3085	−0.7995	0.052*
C25	−0.6173 (7)	−0.3905 (4)	−0.6610 (15)	0.0439 (17)
H25	−0.5897	−0.4291	−0.7778	0.053*
C26	−0.7157 (6)	−0.4063 (3)	−0.4766 (13)	0.0355 (15)
H26	−0.7534	−0.4559	−0.4631	0.043*
O1	−1.2134 (7)	−0.4269 (3)	0.2455 (15)	0.091 (3)
O10	−1.1774 (5)	−0.4021 (3)	−0.1724 (12)	0.0454 (14)	0.50
N1	−1.1774 (5)	−0.4021 (3)	−0.1724 (12)	0.0454 (14)	0.50
H1	−1.1181	−0.4008	−0.3019	0.054*	0.50
O2	−0.9122 (4)	−0.4354 (2)	−0.1312 (8)	0.0317 (10)
O20	−0.9026 (5)	−0.3182 (2)	0.0368 (9)	0.0403 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.044 (4)	0.020 (3)	0.052 (4)	−0.002 (3)	0.014 (4)	0.001 (3)
C2	0.036 (3)	0.028 (3)	0.031 (3)	−0.005 (3)	−0.001 (3)	−0.002 (3)
C10	0.050 (4)	0.058 (5)	0.094 (7)	0.019 (4)	−0.024 (5)	−0.018 (5)
C20	0.030 (3)	0.020 (3)	0.046 (4)	0.000 (2)	−0.002 (3)	0.002 (3)
C21	0.028 (3)	0.024 (3)	0.038 (4)	0.002 (2)	−0.001 (3)	0.004 (3)
C22	0.040 (3)	0.028 (3)	0.046 (4)	0.000 (3)	0.004 (3)	0.003 (3)
C23	0.040 (4)	0.040 (4)	0.050 (4)	−0.008 (3)	0.006 (4)	0.008 (4)
C24	0.038 (3)	0.043 (4)	0.050 (4)	−0.003 (3)	0.009 (4)	0.006 (4)
C25	0.039 (4)	0.044 (4)	0.049 (4)	0.001 (3)	0.002 (4)	−0.008 (4)
C26	0.031 (3)	0.033 (3)	0.042 (4)	0.000 (2)	−0.005 (3)	−0.002 (3)
O1	0.106 (5)	0.053 (3)	0.115 (6)	0.030 (3)	0.088 (5)	0.028 (4)
O10	0.040 (3)	0.047 (3)	0.050 (3)	0.012 (2)	−0.014 (3)	−0.007 (3)
N1	0.040 (3)	0.047 (3)	0.050 (3)	0.012 (2)	−0.014 (3)	−0.007 (3)
O2	0.033 (2)	0.0234 (19)	0.039 (2)	0.0023 (17)	0.002 (2)	−0.0014 (19)
O20	0.050 (3)	0.026 (2)	0.045 (3)	0.000 (2)	0.009 (3)	−0.006 (2)

Geometric parameters (Å, º)

C1—O1	1.232 (9)	C21—C22	1.373 (8)
C1—O10	1.334 (9)	C21—C26	1.375 (8)
C1—C2	1.499 (9)	C22—C23	1.388 (10)
C2—O2	1.433 (7)	C22—H22	0.9600
C2—C2^i	1.536 (11)	C23—C24	1.383 (10)
C2—H2	0.9600	C23—H23	0.9599
C10—O10	1.466 (8)	C24—C25	1.381 (9)
C10—H101	0.9600	C24—H24	0.9600
C10—H102	0.9600	C25—C26	1.403 (10)
C10—H103	0.9600	C25—H25	0.9600
C20—O20	1.217 (7)	C26—H26	0.9600
C20—O2	1.379 (7)	N1—H1	0.9000
C20—C21	1.486 (9)
O1—C1—O10	124.5 (7)	C26—C21—C20	121.1 (5)
O1—C1—C2	119.8 (7)	C21—C22—C23	119.3 (6)
O10—C1—C2	115.7 (6)	C21—C22—H22	120.6
O2—C2—C1	114.4 (5)	C23—C22—H22	120.1
O2—C2—C2^i	105.9 (4)	C24—C23—C22	120.1 (6)
C1—C2—C2^i	110.0 (6)	C24—C23—H23	120.2
O2—C2—H2	108.5	C22—C23—H23	119.7
C1—C2—H2	109.2	C25—C24—C23	120.3 (7)
C2^i—C2—H2	108.6	C25—C24—H24	120.0
O10—C10—H101	110.4	C23—C24—H24	119.7
O10—C10—H102	109.7	C24—C25—C26	119.7 (7)
H101—C10—H102	109.6	C24—C25—H25	120.4
O10—C10—H103	109.2	C26—C25—H25	119.9
H101—C10—H103	109.6	C21—C26—C25	118.9 (6)
H102—C10—H103	108.2	C21—C26—H26	120.7
O20—C20—O2	121.3 (6)	C25—C26—H26	120.3
O20—C20—C21	126.7 (5)	C1—O10—C10	118.7 (7)
O2—C20—C21	111.9 (5)	C1—O10—H1	120.7
C22—C21—C26	121.6 (6)	C10—O10—H1	120.5
C22—C21—C20	117.3 (6)	C20—O2—C2	115.5 (5)
O1—C1—C2—O2	−164.0 (6)	C22—C23—C24—C25	0.0 (11)
O10—C1—C2—O2	17.4 (8)	C23—C24—C25—C26	−0.8 (11)
O1—C1—C2—C2^i	76.9 (7)	C22—C21—C26—C25	−1.5 (9)
O10—C1—C2—C2^i	−101.7 (5)	C20—C21—C26—C25	178.4 (6)
O20—C20—C21—C22	−2.3 (10)	C24—C25—C26—C21	1.5 (10)
O2—C20—C21—C22	178.9 (6)	O1—C1—O10—C10	−3.3 (10)
O20—C20—C21—C26	177.8 (6)	C2—C1—O10—C10	175.3 (5)
O2—C20—C21—C26	−1.0 (8)	O20—C20—O2—C2	−8.7 (8)
C26—C21—C22—C23	0.7 (10)	C21—C20—O2—C2	170.2 (5)
C20—C21—C22—C23	−179.2 (6)	C1—C2—O2—C20	77.8 (6)
C21—C22—C23—C24	0.1 (11)	C2^i—C2—O2—C20	−160.8 (5)

Symmetry code: (i) −x−2, −y−1, z.