Chiral versus racemic building blocks in supra­molecular chemistry: tartrate salts of organic diamines

Farrell, D.M.M.; Ferguson, G.; Lough, A.J.; Glidewell, C.

doi:10.1107/S0108768101019632

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Chiral versus racemic building blocks in supramolecular chemistry: tartrate salts of organic diamines

D. M. M. Farrell, G. Ferguson, A. J. Lough and C. Glidewell

In the 1:1 adducts C₁₂H₁₀N₂·C₄H₆O₆ formed between 1,2-bis(4′-pyridyl)ethene and racemic tartaric acid [(I), triclinic P $\bar 1$ , Z′ = 1] and (2R,3R)-tartaric acid [(II), triclinic P1, Z′ = 2], the ionic components are linked by hard hydrogen bonds into single sheets, which are further linked by C—H

O hydrogen bonds. In the analogous adducts C₁₀H₁₈N₂·C₄H₆O₆ formed by 4,4′-bipyridyl with racemic tartaric acid [(III), triclinic P $\bar 1$ , Z′ = 1] and the chiral acid [(IV), monoclinic P2₁, Z′ = 1], the hard hydrogen bonds generate bilayers which are again linked by C—H

O hydrogen bonds. Piperazine forms a 1:1 salt [{(C₄H₁₀N₂)H₂}²⁺]·[(C₄H₄O₆)²⁻] with (2R,3R)-tartaric acid [(V), monoclinic P2₁] sheets, which are linked by the cations to form a pillared-layer framework. In each of the 1:2 salts formed by racemic tartaric acid with piperazine [(VI), monoclinic P2₁/n, Z′ = 0.5] and 1,4-diazabicyclo[2.2.2]octane (DABCO) [(VII), monoclinic P2₁/n, Z′ = 0.5], the cation lies across a centre of inversion, with the [{HN(CH₂CH₂)₃NH}²⁺] cation disordered over two sets of sites: in both (VI) and (VII) the anions form a three-dimensional framework encapsulating large voids which accommodate the cations. The salt formed between DABCO and (2R,3R)-tartaric acid [(VIII), orthorhombic P2₁2₁2₁, Z′ = 1] has 3:4 stoichiometry and contains four different types of ion, [{HN(CH₂CH₂)₃NH}²⁺]₂·[N(CH₂CH₂)₃NH]⁺·3(C₄H₅O₆)⁻·C₄H₄O₆²⁻: the hard hydrogen bonds generate a three-dimensional framework.

Keywords: chiral; racemic; supramolecular chemistry; adducts; hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768101019632/na0130sup1.cif Contains datablocks global, I, II, III, IV, V, VI, VII, VIII
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768101019632/na0130Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768101019632/na0130IIsup3.hkl Contains datablock II
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768101019632/na0130IIIsup4.hkl Contains datablock III
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768101019632/na0130IVsup5.hkl Contains datablock IV
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768101019632/na0130Vsup6.hkl Contains datablock V
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768101019632/na0130VIsup7.hkl Contains datablock VI
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768101019632/na0130VIIsup8.hkl Contains datablock VII
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768101019632/na0130VIIIsup9.hkl Contains datablock VIII

CCDC references: 184891; 184892; 184893; 184894; 184895; 184896; 184897; 184898

Computing details top

For all compounds, data collection: Kappa-CCD server software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997b) and PRPKAPPA (Ferguson, 1999).

(I) 1,2-Bis-(4'-pyridyl)ethene–racemic tartaric acid (1/1) top

Crystal data top

C₁₆H₁₆N₂O₆	Z = 2
M_r = 332.31	F(000) = 348
Triclinic, P1	D_x = 1.461 Mg m⁻³
a = 8.8780 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.6130 (13) Å	Cell parameters from 2118 reflections
c = 10.1020 (13) Å	θ = 3.0–25.1°
α = 73.665 (7)°	µ = 0.11 mm⁻¹
β = 66.433 (8)°	T = 150 K
γ = 79.141 (6)°	Needle, colourless
V = 755.51 (17) Å³	0.40 × 0.14 × 0.10 mm

Data collection top

Kappa-CCD diffractometer	2621 independent reflections
Radiation source: fine-focus sealed X-ray tube	1709 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
φ scans, and ω scans with κ offsets	θ_max = 25.1°, θ_min = 3.0°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→10
T_min = 0.956, T_max = 0.989	k = −10→11
5383 measured reflections	l = −10→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.052	H-atom parameters constrained
wR(F²) = 0.144	w = 1/[σ²(F_o²) + (0.0568P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2621 reflections	Δρ_max = 0.21 e Å⁻³
247 parameters	Δρ_min = −0.23 e Å⁻³
17 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (7)

Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.4055 (2)	0.87612 (16)	0.47579 (19)	0.0337 (5)	0.915 (2)
O2	0.2343 (2)	0.84545 (16)	0.3757 (2)	0.0362 (5)	0.915 (2)
O3	0.1591 (3)	1.3510 (2)	0.1831 (3)	0.0398 (6)	0.915 (2)
O4	0.1355 (3)	1.41090 (19)	0.3891 (2)	0.0449 (6)	0.915 (2)
O5	0.4384 (2)	1.15481 (17)	0.3299 (2)	0.0341 (5)	0.915 (2)
O6	0.1003 (2)	1.12484 (19)	0.5456 (2)	0.0331 (5)	0.915 (2)
C1	0.3198 (4)	0.9209 (3)	0.3965 (3)	0.0298 (7)	0.915 (2)
C2	0.3185 (3)	1.0840 (3)	0.3207 (3)	0.0282 (7)	0.915 (2)
C3	0.1451 (3)	1.1569 (3)	0.3897 (3)	0.0279 (7)	0.915 (2)
C4	0.1454 (3)	1.3211 (3)	0.3231 (3)	0.0299 (7)	0.915 (2)
N11	0.3648 (2)	0.60208 (19)	0.6138 (2)	0.0309 (5)
C12	0.4337 (3)	0.5445 (2)	0.7146 (3)	0.0329 (6)
C13	0.4079 (3)	0.4033 (2)	0.7966 (3)	0.0325 (6)
C14	0.3113 (3)	0.3211 (2)	0.7727 (3)	0.0288 (6)
C15	0.2433 (3)	0.3856 (2)	0.6646 (3)	0.0306 (6)
C16	0.2712 (3)	0.5266 (2)	0.5878 (3)	0.0314 (6)
C17	0.2829 (3)	0.1722 (2)	0.8622 (3)	0.0322 (6)
N21	0.1429 (3)	−0.3652 (2)	1.0706 (2)	0.0326 (6)
C22	0.1199 (3)	−0.3111 (2)	0.9426 (3)	0.0325 (6)
C23	0.1456 (3)	−0.1689 (2)	0.8625 (3)	0.0296 (6)
C24	0.1973 (3)	−0.0764 (2)	0.9162 (3)	0.0272 (6)
C25	0.2164 (3)	−0.1315 (2)	1.0515 (3)	0.0344 (7)
C26	0.1877 (3)	−0.2753 (3)	1.1245 (3)	0.0352 (7)
C27	0.2278 (3)	0.0732 (2)	0.8287 (3)	0.0295 (6)
O31	0.4055 (2)	0.87612 (16)	0.47579 (19)	0.0337 (5)	0.085 (2)
O32	0.2343 (2)	0.84545 (16)	0.3757 (2)	0.0362 (5)	0.085 (2)
O33	0.108 (2)	1.376 (2)	0.228 (3)	0.036 (3)*	0.085 (2)
O34	0.380 (2)	1.3774 (16)	0.114 (2)	0.036 (3)*	0.085 (2)
O35	0.311 (3)	1.1716 (15)	0.440 (2)	0.036 (3)*	0.085 (2)
O36	0.429 (2)	1.0906 (16)	0.144 (2)	0.036 (3)*	0.085 (2)
C31	0.298 (2)	0.9250 (14)	0.417 (2)	0.036 (3)*	0.085 (2)
C32	0.236 (2)	1.0884 (17)	0.390 (2)	0.036 (3)*	0.085 (2)
C33	0.268 (2)	1.1466 (14)	0.2257 (19)	0.036 (3)*	0.085 (2)
C34	0.2581 (19)	1.3142 (15)	0.186 (2)	0.040*	0.085 (2)
H3	0.1625	1.4411	0.1478	0.060*	0.915 (2)
H5	0.4604	1.1105	0.4053	0.051*	0.915 (2)
H6	−0.0027	1.1378	0.5864	0.050*	0.915 (2)
H2	0.3414	1.0936	0.2134	0.034*	0.915 (2)
H3A	0.0650	1.1170	0.3660	0.033*	0.915 (2)
H11	0.3812	0.6923	0.5628	0.037*
H12	0.5003	0.6002	0.7303	0.040*
H13	0.4561	0.3622	0.8693	0.039*
H15	0.1782	0.3323	0.6444	0.037*
H16	0.2237	0.5713	0.5152	0.038*
H17	0.3058	0.1450	0.9506	0.039*
H22	0.0841	−0.3730	0.9044	0.039*
H23	0.1278	−0.1352	0.7715	0.036*
H25	0.2489	−0.0714	1.0940	0.041*
H26	0.2007	−0.3111	1.2174	0.042*
H27	0.2057	0.1014	0.7398	0.035*
H32	0.1147	1.0976	0.4461	0.043*	0.085 (2)
H33	0.1849	1.1132	0.2008	0.043*	0.085 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0413 (11)	0.0259 (9)	0.0356 (12)	−0.0072 (7)	−0.0196 (9)	0.0013 (8)
O2	0.0444 (12)	0.0265 (9)	0.0416 (12)	−0.0066 (8)	−0.0200 (10)	−0.0053 (8)
O3	0.0666 (18)	0.0210 (11)	0.0336 (16)	−0.0061 (10)	−0.0243 (13)	0.0013 (9)
O4	0.0720 (17)	0.0273 (11)	0.0420 (14)	−0.0022 (9)	−0.0282 (13)	−0.0085 (9)
O5	0.0368 (12)	0.0251 (10)	0.0400 (14)	−0.0094 (8)	−0.0168 (10)	0.0015 (8)
O6	0.0344 (12)	0.0334 (10)	0.0272 (12)	−0.0041 (8)	−0.0089 (9)	−0.0035 (8)
C1	0.0363 (17)	0.0232 (14)	0.0286 (18)	−0.0043 (11)	−0.0108 (15)	−0.0044 (12)
C2	0.0320 (16)	0.0240 (14)	0.0264 (17)	−0.0054 (11)	−0.0108 (14)	−0.0004 (11)
C3	0.0361 (17)	0.0247 (14)	0.0234 (16)	−0.0072 (11)	−0.0127 (13)	−0.0006 (11)
C4	0.0321 (17)	0.0262 (14)	0.0336 (19)	−0.0020 (11)	−0.0162 (15)	−0.0046 (13)
N11	0.0330 (13)	0.0221 (10)	0.0292 (13)	−0.0034 (8)	−0.0052 (11)	−0.0022 (9)
C12	0.0334 (15)	0.0271 (14)	0.0374 (17)	−0.0048 (10)	−0.0116 (13)	−0.0066 (11)
C13	0.0372 (16)	0.0243 (13)	0.0327 (16)	−0.0032 (11)	−0.0125 (13)	−0.0016 (11)
C14	0.0287 (14)	0.0226 (12)	0.0272 (15)	−0.0022 (10)	−0.0044 (12)	−0.0028 (10)
C15	0.0314 (15)	0.0266 (13)	0.0293 (16)	−0.0051 (10)	−0.0073 (13)	−0.0038 (11)
C16	0.0319 (15)	0.0289 (14)	0.0269 (16)	−0.0011 (10)	−0.0057 (12)	−0.0052 (11)
C17	0.0382 (16)	0.0268 (13)	0.0283 (16)	−0.0053 (11)	−0.0137 (13)	0.0025 (11)
N21	0.0367 (13)	0.0267 (11)	0.0326 (14)	−0.0054 (9)	−0.0129 (11)	−0.0019 (9)
C22	0.0332 (15)	0.0282 (13)	0.0351 (17)	−0.0035 (10)	−0.0107 (13)	−0.0080 (11)
C23	0.0320 (15)	0.0261 (13)	0.0273 (15)	−0.0033 (10)	−0.0109 (12)	−0.0005 (10)
C24	0.0268 (14)	0.0241 (12)	0.0259 (15)	−0.0016 (10)	−0.0070 (12)	−0.0032 (10)
C25	0.0473 (18)	0.0262 (14)	0.0330 (17)	−0.0076 (11)	−0.0182 (14)	−0.0036 (11)
C26	0.0402 (16)	0.0311 (14)	0.0324 (17)	−0.0052 (11)	−0.0156 (14)	0.0003 (11)
C27	0.0324 (15)	0.0250 (13)	0.0267 (15)	−0.0031 (10)	−0.0082 (12)	−0.0027 (11)
O31	0.0413 (11)	0.0259 (9)	0.0356 (12)	−0.0072 (7)	−0.0196 (9)	0.0013 (8)
O32	0.0444 (12)	0.0265 (9)	0.0416 (12)	−0.0066 (8)	−0.0200 (10)	−0.0053 (8)

Geometric parameters (Å, º) top

O1—C1	1.255 (3)	C16—H16	0.95
O2—C1	1.251 (3)	C17—C27	1.322 (3)
O3—C4	1.321 (4)	C17—H17	0.95
O3—H3	0.84	N21—C26	1.329 (3)
O4—C4	1.203 (3)	N21—C22	1.334 (3)
O5—C2	1.411 (3)	C22—C23	1.387 (3)
O5—H5	0.84	C22—H22	0.95
O6—C3	1.417 (3)	C23—C24	1.386 (3)
O6—H6	0.84	C23—H23	0.95
C1—C2	1.540 (4)	C24—C25	1.387 (3)
C2—C3	1.535 (4)	C24—C27	1.471 (3)
C2—H2	1.00	C25—C26	1.388 (3)
C3—C4	1.531 (3)	C25—H25	0.95
C3—H3A	1.00	C26—H26	0.95
N11—C12	1.331 (3)	C27—H27	0.95
N11—C16	1.339 (3)	O33—C34	1.306 (10)
N11—H11	0.88	O34—C34	1.201 (9)
C12—C13	1.384 (3)	O35—C32	1.418 (10)
C12—H12	0.95	O36—C33	1.424 (10)
C13—C14	1.396 (3)	C31—C32	1.548 (10)
C13—H13	0.95	C32—C33	1.52 (2)
C14—C15	1.395 (3)	C32—H32	1.00
C14—C17	1.468 (3)	C33—C34	1.541 (7)
C15—C16	1.373 (3)	C33—H33	1.00
C15—H15	0.95

O2—C1—O1	125.9 (2)	C27—C17—H17	117.6
O2—C1—C2	117.6 (2)	C14—C17—H17	117.6
O1—C1—C2	116.5 (2)	C26—N21—C22	117.4 (2)
O5—C2—C3	110.6 (2)	N21—C22—C23	123.2 (2)
O5—C2—C1	113.5 (2)	N21—C22—H22	118.4
C3—C2—C1	108.6 (2)	C23—C22—H22	118.4
O5—C2—H2	108.0	C24—C23—C22	119.4 (2)
C3—C2—H2	108.0	C24—C23—H23	120.3
C1—C2—H2	108.0	C22—C23—H23	120.3
O6—C3—C4	111.6 (2)	C23—C24—C25	117.3 (2)
O6—C3—C2	108.8 (2)	C23—C24—C27	119.0 (2)
C4—C3—C2	109.0 (2)	C25—C24—C27	123.7 (2)
O6—C3—H3A	109.1	C24—C25—C26	119.5 (2)
C4—C3—H3A	109.1	C24—C25—H25	120.3
C2—C3—H3A	109.1	C26—C25—H25	120.3
O4—C4—O3	124.4 (3)	N21—C26—C25	123.2 (2)
O4—C4—C3	124.6 (3)	N21—C26—H26	118.4
O3—C4—C3	111.0 (2)	C25—C26—H26	118.4
C12—N11—C16	121.9 (2)	C17—C27—C24	126.2 (2)
C12—N11—H11	119.1	C17—C27—H27	116.9
C16—N11—H11	119.1	C24—C27—H27	116.9
N11—C12—C13	119.7 (2)	O35—C32—C33	110.6 (13)
N11—C12—H12	120.1	O35—C32—C31	112.7 (10)
C13—C12—H12	120.1	C33—C32—C31	108.8 (11)
C12—C13—C14	120.1 (2)	O35—C32—H32	108.2
C12—C13—H13	119.9	C33—C32—H32	108.2
C14—C13—H13	119.9	C31—C32—H32	108.2
C15—C14—C13	118.1 (2)	O36—C33—C32	108.3 (12)
C15—C14—C17	122.5 (2)	O36—C33—C34	109.6 (8)
C13—C14—C17	119.5 (2)	C32—C33—C34	110.6 (12)
C16—C15—C14	119.4 (2)	O36—C33—H33	109.5
C16—C15—H15	120.3	C32—C33—H33	109.5
C14—C15—H15	120.3	C34—C33—H33	109.5
N11—C16—C15	120.8 (2)	O34—C34—O33	125.3 (14)
N11—C16—H16	119.6	O34—C34—C33	120.7 (10)
C15—C16—H16	119.6	O33—C34—C33	113.9 (10)
C27—C17—C14	124.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O1	0.88	1.75	2.628 (2)	175
O3—H3···N21ⁱ	0.84	1.81	2.645 (3)	172
O5—H5···O1	0.84	2.25	2.677 (2)	112
O5—H5···O1ⁱⁱ	0.84	2.04	2.748 (3)	142
O6—H6···O2ⁱⁱⁱ	0.84	1.92	2.731 (3)	162
C27—H27···O6^iv	0.95	2.43	3.359 (3)	165

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

(II) 1,2-Bis-(4'-pyridyl)ethene–(2R,3R)-tartaric acid (1/) top

Crystal data top

C₁₂H₁₁N₂·C₁₂H₁₀N₂·C₄H₆O₆·C₄H₅O₆	Z = 1
M_r = 664.62	F(000) = 348
Triclinic, P1	D_x = 1.487 Mg m⁻³
a = 8.6195 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.5654 (4) Å	Cell parameters from 3134 reflections
c = 9.8727 (4) Å	θ = 2.7–27.5°
α = 103.1622 (18)°	µ = 0.12 mm⁻¹
β = 109.9123 (18)°	T = 150 K
γ = 90.262 (3)°	Needle, colourless
V = 742.22 (5) Å³	0.24 × 0.14 × 0.10 mm

Data collection top

Kappa-CCD diffractometer	3390 independent reflections
Radiation source: fine-focus sealed X-ray tube	1944 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
φ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 2.7°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→11
T_min = 0.973, T_max = 0.989	k = −12→12
8988 measured reflections	l = −12→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.138	w = 1/[σ²(F_o²) + (0.0574P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max = 0.001
3390 reflections	Δρ_max = 0.30 e Å⁻³
442 parameters	Δρ_min = −0.25 e Å⁻³
3 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (3)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O11	0.7906 (3)	−0.3609 (3)	0.0884 (3)	0.0320 (9)
O12	1.0049 (4)	−0.3598 (3)	0.2952 (3)	0.0315 (9)
O13	1.2433 (4)	−0.6049 (3)	−0.1194 (4)	0.0301 (8)
O14	0.9746 (4)	−0.6726 (4)	−0.2444 (3)	0.0398 (11)
O15	1.1136 (4)	−0.5908 (3)	0.1604 (3)	0.0297 (9)
O16	1.1916 (4)	−0.3659 (3)	0.0382 (4)	0.0308 (9)
C11	0.9306 (5)	−0.4068 (5)	0.1644 (5)	0.0245 (11)
C12	0.9873 (5)	−0.5275 (4)	0.0664 (4)	0.0215 (11)
C13	1.0491 (5)	−0.4636 (5)	−0.0396 (5)	0.0234 (11)
C14	1.0875 (5)	−0.5920 (5)	−0.1459 (5)	0.0257 (11)
O21	0.7857 (4)	0.1535 (3)	0.0800 (3)	0.0327 (9)
O22	0.9939 (4)	0.1260 (3)	0.2815 (3)	0.0332 (9)
O23	1.2316 (4)	−0.1029 (3)	−0.1313 (3)	0.0283 (8)
O24	0.9687 (4)	−0.2003 (4)	−0.2441 (4)	0.0388 (10)
O25	1.0875 (4)	−0.0992 (3)	0.1363 (3)	0.0307 (9)
O26	1.1554 (4)	0.1311 (3)	0.0159 (4)	0.0299 (9)
C21	0.9131 (5)	0.0933 (5)	0.1477 (5)	0.0252 (11)
C22	0.9609 (5)	−0.0308 (5)	0.0461 (5)	0.0245 (11)
C23	1.0211 (5)	0.0229 (5)	−0.0630 (5)	0.0260 (12)
C24	1.0770 (5)	−0.1055 (5)	−0.1561 (5)	0.0232 (10)
N31	0.6907 (4)	−0.1542 (4)	0.2531 (4)	0.0274 (9)
C32	0.5490 (5)	−0.0959 (5)	0.1970 (5)	0.0316 (12)
C33	0.5026 (5)	0.0247 (5)	0.2783 (5)	0.0308 (12)
C34	0.6071 (5)	0.0890 (5)	0.4233 (5)	0.0231 (10)
C35	0.7517 (6)	0.0259 (5)	0.4794 (5)	0.0284 (12)
C36	0.7870 (5)	−0.0946 (5)	0.3919 (5)	0.0273 (11)
C37	0.5715 (5)	0.2194 (5)	0.5176 (5)	0.0261 (11)
N41	0.3158 (4)	0.6567 (4)	0.7386 (4)	0.0247 (9)
C42	0.4606 (5)	0.6047 (5)	0.7959 (5)	0.0284 (11)
C43	0.5040 (5)	0.4815 (5)	0.7168 (5)	0.0294 (12)
C44	0.3946 (5)	0.4109 (5)	0.5761 (5)	0.0253 (11)
C45	0.2446 (5)	0.4692 (5)	0.5196 (5)	0.0250 (11)
C46	0.2093 (5)	0.5920 (5)	0.6039 (5)	0.0235 (10)
C47	0.4288 (5)	0.2804 (4)	0.4824 (5)	0.0242 (10)
N51	0.7032 (4)	0.3515 (4)	0.2573 (4)	0.0274 (9)
C52	0.5622 (5)	0.4091 (5)	0.1984 (5)	0.0313 (12)
C53	0.5130 (5)	0.5281 (5)	0.2799 (5)	0.0300 (11)
C54	0.6163 (5)	0.5881 (5)	0.4286 (5)	0.0234 (10)
C55	0.7597 (5)	0.5237 (5)	0.4867 (5)	0.0268 (11)
C56	0.7987 (5)	0.4041 (4)	0.3990 (5)	0.0249 (11)
C57	0.5793 (5)	0.7162 (5)	0.5206 (5)	0.0271 (11)
N61	0.3147 (4)	1.1595 (4)	0.7346 (4)	0.0221 (8)
C62	0.4629 (5)	1.1098 (5)	0.7867 (5)	0.0297 (12)
C63	0.5081 (5)	0.9851 (5)	0.7121 (5)	0.0294 (12)
C64	0.3979 (5)	0.9058 (5)	0.5776 (5)	0.0234 (10)
C65	0.2431 (5)	0.9566 (5)	0.5244 (5)	0.0264 (11)
C66	0.2071 (5)	1.0829 (5)	0.6037 (5)	0.0260 (11)
C67	0.4344 (5)	0.7745 (5)	0.4856 (5)	0.0271 (11)
H11	0.7512	−0.3092	0.1476	0.048*	0.69 (7)
H13	1.2554	−0.6822	−0.1740	0.045*
H15	1.1218	−0.6743	0.1144	0.045*
H16	1.1630	−0.2820	0.0581	0.046*
H12	0.8921	−0.6016	0.0062	0.026*
H13A	0.9587	−0.4131	−0.0983	0.028*
H21	0.7483	0.2486	0.1750	0.049*
H25	1.1227	−0.0484	0.2239	0.046*
H26	1.2400	0.1040	−0.0030	0.045*
H22	0.8620	−0.1019	−0.0109	0.029*
H23	0.9283	0.0643	−0.1304	0.031*
H31	0.7188	−0.2296	0.1995	0.033*	0.31 (7)
H32	0.4777	−0.1383	0.0982	0.038*
H33	0.4009	0.0630	0.2357	0.037*
H35	0.8261	0.0655	0.5777	0.034*
H36	0.8859	−0.1374	0.4334	0.033*
H37	0.6560	0.2628	0.6095	0.031*
H41	0.2900	0.7348	0.7904	0.030*
H42	0.5348	0.6525	0.8918	0.034*
H43	0.6076	0.4453	0.7581	0.035*
H45	0.1677	0.4245	0.4238	0.030*
H46	0.1072	0.6315	0.5654	0.028*
H47	0.3437	0.2366	0.3909	0.029*
H52	0.4938	0.3678	0.0984	0.038*
H53	0.4126	0.5679	0.2366	0.036*
H55	0.8311	0.5615	0.5864	0.032*
H56	0.8954	0.3587	0.4407	0.030*
H57	0.6638	0.7614	0.6119	0.033*
H62	0.5404	1.1623	0.8790	0.036*
H63	0.6148	0.9539	0.7532	0.035*
H65	0.1624	0.9045	0.4338	0.032*
H66	0.1018	1.1172	0.5643	0.031*
H67	0.3491	0.7283	0.3953	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O11	0.0232 (15)	0.037 (2)	0.0286 (18)	0.0107 (15)	0.0083 (14)	−0.0037 (17)
O12	0.0376 (18)	0.029 (2)	0.025 (2)	0.0115 (15)	0.0105 (15)	0.0022 (16)
O13	0.0317 (18)	0.0250 (19)	0.034 (2)	0.0035 (14)	0.0183 (16)	−0.0019 (15)
O14	0.0306 (17)	0.050 (3)	0.0290 (19)	0.0077 (18)	0.0063 (15)	−0.0034 (19)
O15	0.036 (2)	0.0237 (19)	0.028 (2)	0.0095 (15)	0.0096 (16)	0.0065 (16)
O16	0.033 (2)	0.0189 (18)	0.041 (2)	0.0028 (16)	0.0152 (18)	0.0056 (16)
C11	0.028 (3)	0.018 (2)	0.029 (3)	0.0028 (19)	0.013 (2)	0.005 (2)
C12	0.023 (2)	0.020 (2)	0.020 (2)	0.0037 (19)	0.0070 (19)	0.002 (2)
C13	0.024 (2)	0.020 (3)	0.024 (3)	0.007 (2)	0.008 (2)	0.003 (2)
C14	0.027 (2)	0.028 (3)	0.025 (3)	0.009 (2)	0.010 (2)	0.012 (2)
O21	0.0321 (17)	0.033 (2)	0.0267 (19)	0.0089 (15)	0.0103 (15)	−0.0039 (15)
O22	0.042 (2)	0.034 (2)	0.024 (2)	0.0133 (16)	0.0130 (16)	0.0049 (17)
O23	0.0317 (18)	0.0238 (18)	0.0328 (19)	0.0052 (14)	0.0196 (15)	0.0004 (15)
O24	0.0331 (17)	0.038 (3)	0.0328 (19)	0.0025 (17)	0.0057 (15)	−0.0068 (18)
O25	0.045 (2)	0.0260 (19)	0.027 (2)	0.0136 (16)	0.0185 (18)	0.0088 (16)
O26	0.036 (2)	0.0225 (18)	0.036 (2)	0.0032 (16)	0.0219 (18)	0.0021 (16)
C21	0.029 (3)	0.023 (2)	0.029 (3)	0.006 (2)	0.018 (2)	0.005 (2)
C22	0.028 (3)	0.019 (2)	0.029 (3)	0.0073 (19)	0.013 (2)	0.007 (2)
C23	0.030 (3)	0.018 (3)	0.029 (3)	0.003 (2)	0.012 (2)	0.003 (2)
C24	0.030 (2)	0.022 (3)	0.020 (2)	0.008 (2)	0.011 (2)	0.006 (2)
N31	0.029 (2)	0.026 (2)	0.027 (2)	0.0057 (17)	0.0121 (18)	0.0007 (18)
C32	0.037 (3)	0.029 (3)	0.027 (3)	0.009 (2)	0.013 (2)	0.001 (2)
C33	0.028 (2)	0.028 (3)	0.038 (3)	0.013 (2)	0.014 (2)	0.008 (2)
C34	0.033 (2)	0.019 (2)	0.027 (3)	0.0062 (19)	0.020 (2)	0.007 (2)
C35	0.028 (2)	0.026 (3)	0.028 (3)	−0.001 (2)	0.012 (2)	−0.001 (2)
C36	0.026 (2)	0.026 (3)	0.032 (3)	0.004 (2)	0.014 (2)	0.005 (2)
C37	0.029 (2)	0.026 (3)	0.024 (2)	0.000 (2)	0.013 (2)	0.002 (2)
N41	0.029 (2)	0.022 (2)	0.027 (2)	0.0079 (16)	0.0163 (17)	0.0037 (18)
C42	0.027 (2)	0.028 (3)	0.025 (3)	0.006 (2)	0.006 (2)	0.001 (2)
C43	0.024 (2)	0.030 (3)	0.034 (3)	0.008 (2)	0.010 (2)	0.009 (2)
C44	0.034 (2)	0.020 (3)	0.032 (3)	0.003 (2)	0.022 (2)	0.008 (2)
C45	0.027 (2)	0.025 (3)	0.024 (2)	0.0023 (19)	0.0116 (19)	0.003 (2)
C46	0.023 (2)	0.026 (3)	0.022 (2)	0.0005 (18)	0.0094 (18)	0.006 (2)
C47	0.025 (2)	0.020 (2)	0.027 (2)	0.0000 (18)	0.0110 (19)	0.002 (2)
N51	0.028 (2)	0.025 (2)	0.030 (2)	0.0051 (17)	0.0135 (17)	0.0016 (18)
C52	0.029 (2)	0.030 (3)	0.031 (3)	0.006 (2)	0.009 (2)	0.004 (2)
C53	0.030 (2)	0.026 (3)	0.035 (3)	0.007 (2)	0.013 (2)	0.008 (2)
C54	0.025 (2)	0.020 (2)	0.025 (3)	−0.0025 (19)	0.011 (2)	0.001 (2)
C55	0.024 (2)	0.028 (3)	0.023 (3)	−0.0029 (19)	0.006 (2)	−0.001 (2)
C56	0.024 (2)	0.021 (3)	0.031 (3)	0.0038 (19)	0.014 (2)	0.003 (2)
C57	0.030 (2)	0.024 (3)	0.029 (3)	0.0011 (19)	0.012 (2)	0.007 (2)
N61	0.0233 (18)	0.019 (2)	0.025 (2)	0.0074 (15)	0.0094 (16)	0.0059 (17)
C62	0.028 (2)	0.029 (3)	0.028 (3)	0.000 (2)	0.008 (2)	0.003 (2)
C63	0.027 (2)	0.030 (3)	0.034 (3)	0.008 (2)	0.015 (2)	0.008 (2)
C64	0.027 (2)	0.019 (2)	0.026 (2)	0.0058 (19)	0.013 (2)	0.006 (2)
C65	0.026 (2)	0.029 (3)	0.023 (2)	0.0015 (19)	0.0077 (19)	0.005 (2)
C66	0.021 (2)	0.031 (3)	0.030 (3)	0.0050 (19)	0.0118 (19)	0.011 (2)
C67	0.029 (2)	0.027 (3)	0.029 (3)	−0.0004 (19)	0.017 (2)	0.004 (2)

Geometric parameters (Å, º) top

O11—C11	1.323 (5)	C37—C47	1.335 (5)
O11—H11	0.84	C37—H37	0.95
O12—C11	1.204 (5)	N41—C42	1.333 (6)
O13—C14	1.290 (5)	N41—C46	1.335 (5)
O13—H13	0.84	N41—H41	0.88
O14—C14	1.222 (5)	C42—C43	1.386 (6)
O15—C12	1.409 (5)	C42—H42	0.95
O15—H15	0.84	C43—C44	1.396 (6)
O16—C13	1.411 (5)	C43—H43	0.95
O16—H16	0.84	C44—C45	1.397 (6)
C11—C12	1.525 (6)	C44—C47	1.471 (6)
C12—C13	1.556 (5)	C45—C46	1.377 (6)
C12—H12	1.00	C45—H45	0.95
C13—C14	1.541 (6)	C46—H46	0.95
C13—H13A	1.00	C47—H47	0.95
O21—C21	1.290 (5)	N51—C56	1.334 (5)
O21—H21	1.2770	N51—C52	1.337 (6)
O22—C21	1.229 (5)	C52—C53	1.394 (6)
O23—C24	1.270 (5)	C52—H52	0.95
O24—C24	1.237 (5)	C53—C54	1.413 (6)
O25—C22	1.422 (5)	C53—H53	0.95
O25—H25	0.84	C54—C55	1.386 (6)
O26—C23	1.424 (5)	C54—C57	1.457 (6)
O26—H26	0.84	C55—C56	1.387 (6)
C21—C22	1.526 (6)	C55—H55	0.95
C22—C23	1.524 (5)	C56—H56	0.95
C22—H22	1.00	C57—C67	1.338 (5)
C23—C24	1.542 (5)	C57—H57	0.95
C23—H23	1.00	N61—C62	1.339 (6)
N31—C36	1.326 (5)	N61—C66	1.346 (5)
N31—C32	1.340 (6)	C62—C63	1.384 (6)
N31—H31	0.88	C62—H62	0.95
C32—C33	1.391 (6)	C63—C64	1.384 (6)
C32—H32	0.95	C63—H63	0.95
C33—C34	1.398 (6)	C64—C65	1.392 (6)
C33—H33	0.95	C64—C67	1.476 (6)
C34—C35	1.383 (6)	C65—C66	1.381 (6)
C34—C37	1.478 (6)	C65—H65	0.95
C35—C36	1.377 (6)	C66—H66	0.95
C35—H35	0.95	C67—H67	0.95
C36—H36	0.95

C11—O11—H11	109.5	C47—C37—H37	117.7
C14—O13—H13	109.5	C34—C37—H37	117.7
C12—O15—H15	109.5	C42—N41—C46	121.0 (4)
C13—O16—H16	109.5	C42—N41—H41	119.5
O12—C11—O11	124.4 (4)	C46—N41—H41	119.5
O12—C11—C12	123.7 (4)	N41—C42—C43	120.6 (4)
O11—C11—C12	111.9 (4)	N41—C42—H42	119.7
O15—C12—C11	107.8 (3)	C43—C42—H42	119.7
O15—C12—C13	111.9 (3)	C42—C43—C44	119.6 (4)
C11—C12—C13	109.1 (3)	C42—C43—H43	120.2
O15—C12—H12	109.4	C44—C43—H43	120.2
C11—C12—H12	109.4	C43—C44—C45	118.0 (4)
C13—C12—H12	109.4	C43—C44—C47	124.1 (4)
O16—C13—C14	110.2 (3)	C45—C44—C47	117.9 (4)
O16—C13—C12	112.2 (3)	C46—C45—C44	119.4 (4)
C14—C13—C12	106.7 (3)	C46—C45—H45	120.3
O16—C13—H13A	109.2	C44—C45—H45	120.3
C14—C13—H13A	109.2	N41—C46—C45	121.3 (4)
C12—C13—H13A	109.2	N41—C46—H46	119.3
O14—C14—O13	125.3 (4)	C45—C46—H46	119.3
O14—C14—C13	120.2 (4)	C37—C47—C44	124.3 (4)
O13—C14—C13	114.5 (4)	C37—C47—H47	117.9
C21—O21—H21	109.5	C44—C47—H47	117.9
C22—O25—H25	109.5	C56—N51—C52	120.4 (4)
C23—O26—H26	109.5	N51—C52—C53	121.8 (4)
O22—C21—O21	126.4 (4)	N51—C52—H52	119.1
O22—C21—C22	119.5 (4)	C53—C52—H52	119.1
O21—C21—C22	114.1 (4)	C52—C53—C54	118.4 (4)
O25—C22—C23	110.3 (3)	C52—C53—H53	120.8
O25—C22—C21	108.3 (4)	C54—C53—H53	120.8
C23—C22—C21	111.2 (3)	C55—C54—C53	118.2 (4)
O25—C22—H22	109.0	C55—C54—C57	119.3 (4)
C23—C22—H22	109.0	C53—C54—C57	122.4 (4)
C21—C22—H22	109.0	C54—C55—C56	119.9 (4)
O26—C23—C22	109.9 (3)	C54—C55—H55	120.0
O26—C23—C24	110.1 (3)	C56—C55—H55	120.0
C22—C23—C24	108.8 (3)	N51—C56—C55	121.3 (4)
O26—C23—H23	109.3	N51—C56—H56	119.4
C22—C23—H23	109.3	C55—C56—H56	119.4
C24—C23—H23	109.3	C67—C57—C54	124.6 (4)
O24—C24—O23	127.0 (4)	C67—C57—H57	117.7
O24—C24—C23	117.4 (4)	C54—C57—H57	117.7
O23—C24—C23	115.6 (4)	C62—N61—C66	117.4 (4)
C36—N31—C32	117.8 (4)	N61—C62—C63	122.9 (4)
C36—N31—H31	121.1	N61—C62—H62	118.6
C32—N31—H31	121.1	C63—C62—H62	118.6
N31—C32—C33	122.3 (4)	C64—C63—C62	120.0 (4)
N31—C32—H32	118.8	C64—C63—H63	120.0
C33—C32—H32	118.8	C62—C63—H63	120.0
C32—C33—C34	119.4 (4)	C63—C64—C65	117.1 (4)
C32—C33—H33	120.3	C63—C64—C67	124.8 (4)
C34—C33—H33	120.3	C65—C64—C67	118.1 (4)
C35—C34—C33	117.2 (4)	C66—C65—C64	119.8 (4)
C35—C34—C37	119.1 (4)	C66—C65—H65	120.1
C33—C34—C37	123.7 (4)	C64—C65—H65	120.1
C36—C35—C34	119.6 (4)	N61—C66—C65	122.8 (4)
C36—C35—H35	120.2	N61—C66—H66	118.6
C34—C35—H35	120.2	C65—C66—H66	118.6
N31—C36—C35	123.6 (5)	C57—C67—C64	124.5 (4)
N31—C36—H36	118.2	C57—C67—H67	117.7
C35—C36—H36	118.2	C64—C67—H67	117.7
C47—C37—C34	124.5 (4)

O12—C11—C12—O15	12.8 (6)	C33—C34—C37—C47	8.1 (7)
O11—C11—C12—O15	−167.1 (3)	C46—N41—C42—C43	−0.2 (7)
O12—C11—C12—C13	−108.9 (5)	N41—C42—C43—C44	−0.3 (7)
O11—C11—C12—C13	71.3 (4)	C42—C43—C44—C45	0.7 (6)
O15—C12—C13—O16	−54.3 (4)	C42—C43—C44—C47	179.5 (4)
C11—C12—C13—O16	64.9 (4)	C43—C44—C45—C46	−0.6 (6)
O15—C12—C13—C14	66.5 (4)	C47—C44—C45—C46	−179.5 (4)
C11—C12—C13—C14	−174.3 (4)	C42—N41—C46—C45	0.3 (7)
O16—C13—C14—O14	−165.0 (4)	C44—C45—C46—N41	0.1 (7)
C12—C13—C14—O14	72.9 (5)	C34—C37—C47—C44	−179.4 (4)
O16—C13—C14—O13	15.9 (5)	C43—C44—C47—C37	−3.9 (7)
C12—C13—C14—O13	−106.2 (4)	C45—C44—C47—C37	174.9 (4)
O22—C21—C22—O25	7.0 (5)	C56—N51—C52—C53	2.4 (7)
O21—C21—C22—O25	−172.3 (4)	N51—C52—C53—C54	0.0 (7)
O22—C21—C22—C23	−114.3 (4)	C52—C53—C54—C55	−1.3 (6)
O21—C21—C22—C23	66.4 (5)	C52—C53—C54—C57	177.3 (4)
O25—C22—C23—O26	−64.0 (4)	C53—C54—C55—C56	0.3 (6)
C21—C22—C23—O26	56.1 (5)	C57—C54—C55—C56	−178.3 (4)
O25—C22—C23—C24	56.6 (4)	C52—N51—C56—C55	−3.4 (6)
C21—C22—C23—C24	176.7 (4)	C54—C55—C56—N51	2.0 (7)
O26—C23—C24—O24	−171.7 (4)	C55—C54—C57—C67	−169.4 (4)
C22—C23—C24—O24	67.8 (5)	C53—C54—C57—C67	12.1 (7)
O26—C23—C24—O23	9.5 (5)	C66—N61—C62—C63	0.1 (7)
C22—C23—C24—O23	−111.0 (4)	N61—C62—C63—C64	−0.1 (7)
C36—N31—C32—C33	1.0 (7)	C62—C63—C64—C65	−0.7 (6)
N31—C32—C33—C34	0.6 (7)	C62—C63—C64—C67	177.7 (4)
C32—C33—C34—C35	−1.3 (6)	C63—C64—C65—C66	1.5 (7)
C32—C33—C34—C37	178.4 (4)	C67—C64—C65—C66	−176.9 (4)
C33—C34—C35—C36	0.4 (6)	C62—N61—C66—C65	0.9 (7)
C37—C34—C35—C36	−179.3 (4)	C64—C65—C66—N61	−1.7 (7)
C32—N31—C36—C35	−2.0 (7)	C54—C57—C67—C64	−178.8 (4)
C34—C35—C36—N31	1.3 (7)	C63—C64—C67—C57	−0.4 (7)
C35—C34—C37—C47	−172.2 (4)	C65—C64—C67—C57	177.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···N31	0.84	1.80	2.607 (5)	162
N31—H31···O11	0.88	1.73	2.607 (5)	172
O13—H13···N61ⁱ	0.84	1.75	2.583 (4)	170
O15—H15···O26ⁱⁱ	0.84	1.97	2.806 (4)	176
O16—H16···O25	0.84	1.95	2.781 (4)	169
O21—H21···N51	1.28	1.28	2.551 (5)	173
O25—H25···O22	0.84	2.09	2.597 (4)	119
O26—H26···O23	0.84	2.08	2.595 (4)	119
N41—H41···O23ⁱⁱⁱ	0.88	1.73	2.602 (4)	172
C42—H42···O11^iv	0.95	2.42	3.241 (5)	145
C45—H45···O15^v	0.95	2.45	3.243 (5)	141
C53—H53···O16^v	0.95	2.43	3.320 (6)	156
C62—H62···O21^iv	0.95	2.37	3.202 (5)	145

Symmetry codes: (i) x+1, y−2, z−1; (ii) x, y−1, z; (iii) x−1, y+1, z+1; (iv) x, y+1, z+1; (v) x−1, y+1, z.

(III) 4,4'-Bipyridyl–racemic tartaric acid (1/1) top

Crystal data top

C₁₀H₉N₂·C₄H₅O₆	Z = 2
M_r = 306.27	F(000) = 320
Triclinic, P1	D_x = 1.529 Mg m⁻³
a = 4.7847 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2505 (5) Å	Cell parameters from 2831 reflections
c = 13.8412 (8) Å	θ = 3.0–27.9°
α = 99.434 (2)°	µ = 0.12 mm⁻¹
β = 91.252 (2)°	T = 150 K
γ = 96.163 (2)°	Plate, colourless
V = 665.26 (6) Å³	0.40 × 0.20 × 0.08 mm

Data collection top

Kappa-CCD diffractometer	3049 independent reflections
Radiation source: fine-focus sealed X-ray tube	1936 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
φ scans, and ω scans with κ offsets	θ_max = 27.9°, θ_min = 3.0°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→6
T_min = 0.953, T_max = 0.990	k = −13→13
8786 measured reflections	l = −17→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.134	w = 1/[σ²(F_o²) + (0.0653P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max < 0.001
3049 reflections	Δρ_max = 0.27 e Å⁻³
205 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.019 (6)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N11	0.2544 (3)	0.20324 (16)	0.59042 (12)	0.0269 (4)
C12	0.1952 (4)	0.32372 (19)	0.62979 (14)	0.0257 (5)
C13	0.0131 (4)	0.34124 (19)	0.70597 (14)	0.0255 (5)
C14	−0.1125 (4)	0.23143 (18)	0.74266 (13)	0.0225 (4)
C15	−0.0416 (5)	0.1074 (2)	0.70116 (16)	0.0360 (6)
C16	0.1431 (5)	0.0959 (2)	0.62581 (17)	0.0385 (6)
N21	−0.7003 (3)	0.28193 (17)	0.97151 (12)	0.0286 (4)
C22	−0.5782 (5)	0.1704 (2)	0.95177 (16)	0.0339 (5)
C23	−0.3857 (4)	0.1487 (2)	0.87864 (15)	0.0306 (5)
C24	−0.3117 (4)	0.24868 (19)	0.82355 (14)	0.0236 (4)
C25	−0.4369 (4)	0.36565 (19)	0.84544 (14)	0.0254 (5)
C26	−0.6301 (4)	0.3775 (2)	0.91882 (14)	0.0268 (5)
O1	0.5657 (3)	0.17785 (13)	0.44338 (10)	0.0300 (4)
O2	0.7385 (3)	0.39070 (13)	0.49545 (10)	0.0295 (4)
O5	1.1305 (3)	0.38255 (13)	0.35856 (10)	0.0267 (4)
O6	0.6064 (3)	0.37535 (13)	0.25214 (10)	0.0264 (3)
O3	0.9586 (3)	0.33075 (14)	0.11472 (10)	0.0315 (4)
O4	1.0591 (3)	0.13839 (15)	0.15602 (10)	0.0356 (4)
C1	0.7286 (4)	0.28508 (19)	0.43810 (13)	0.0224 (4)
C2	0.9199 (4)	0.27272 (18)	0.35128 (13)	0.0223 (4)
C3	0.7441 (4)	0.26101 (18)	0.25526 (14)	0.0231 (4)
C4	0.9377 (4)	0.23790 (19)	0.16942 (14)	0.0246 (5)
H11	0.3671	0.1939	0.5410	0.032*	0.60 (4)
H12	0.2793	0.3992	0.6052	0.031*
H13	−0.0263	0.4282	0.7333	0.031*
H15	−0.1206	0.0301	0.7247	0.043*
H16	0.1922	0.0105	0.5986	0.046*
H22	−0.6248	0.1023	0.9895	0.041*
H23	−0.3058	0.0669	0.8664	0.037*
H25	−0.3906	0.4369	0.8105	0.030*
H26	−0.7165	0.4574	0.9321	0.032*
H1	0.4650	0.1912	0.4922	0.045*	0.40 (4)
H5	1.1168	0.4344	0.4115	0.040*
H6	0.4594	0.3708	0.2841	0.040*
H3	1.0751	0.3131	0.0713	0.047*
H2A	1.0139	0.1899	0.3495	0.027*
H3A	0.5988	0.1822	0.2504	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N11	0.0300 (9)	0.0248 (9)	0.0269 (9)	0.0041 (7)	0.0105 (7)	0.0057 (7)
C12	0.0273 (10)	0.0248 (11)	0.0258 (10)	0.0026 (8)	0.0056 (8)	0.0067 (8)
C13	0.0284 (10)	0.0208 (10)	0.0283 (11)	0.0062 (8)	0.0069 (8)	0.0037 (8)
C14	0.0238 (10)	0.0220 (10)	0.0226 (10)	0.0046 (8)	0.0054 (8)	0.0038 (8)
C15	0.0475 (13)	0.0213 (11)	0.0415 (13)	0.0052 (9)	0.0242 (10)	0.0079 (9)
C16	0.0498 (14)	0.0231 (11)	0.0441 (13)	0.0073 (10)	0.0272 (11)	0.0048 (10)
N21	0.0297 (9)	0.0324 (10)	0.0251 (9)	0.0061 (8)	0.0072 (7)	0.0060 (8)
C22	0.0405 (12)	0.0321 (12)	0.0340 (12)	0.0105 (10)	0.0148 (10)	0.0138 (10)
C23	0.0378 (12)	0.0268 (11)	0.0310 (11)	0.0106 (9)	0.0145 (9)	0.0100 (9)
C24	0.0251 (10)	0.0237 (10)	0.0218 (10)	0.0019 (8)	0.0054 (8)	0.0036 (8)
C25	0.0284 (10)	0.0247 (10)	0.0242 (10)	0.0044 (8)	0.0039 (8)	0.0059 (8)
C26	0.0279 (10)	0.0259 (11)	0.0262 (11)	0.0076 (8)	0.0049 (8)	0.0001 (8)
O1	0.0368 (8)	0.0243 (8)	0.0291 (8)	0.0010 (6)	0.0163 (6)	0.0042 (6)
O2	0.0311 (8)	0.0287 (8)	0.0270 (8)	0.0017 (6)	0.0088 (6)	−0.0005 (6)
O5	0.0270 (7)	0.0257 (8)	0.0256 (8)	−0.0004 (6)	0.0082 (6)	0.0006 (6)
O6	0.0253 (7)	0.0281 (8)	0.0285 (8)	0.0080 (6)	0.0095 (6)	0.0080 (6)
O3	0.0369 (8)	0.0349 (8)	0.0277 (8)	0.0134 (7)	0.0168 (6)	0.0119 (7)
O4	0.0491 (9)	0.0288 (8)	0.0327 (9)	0.0152 (7)	0.0181 (7)	0.0072 (7)
C1	0.0240 (10)	0.0234 (10)	0.0214 (10)	0.0058 (8)	0.0053 (8)	0.0061 (8)
C2	0.0229 (9)	0.0201 (10)	0.0240 (10)	0.0024 (8)	0.0078 (7)	0.0034 (8)
C3	0.0244 (10)	0.0215 (10)	0.0241 (10)	0.0036 (8)	0.0075 (8)	0.0045 (8)
C4	0.0271 (10)	0.0233 (10)	0.0232 (10)	0.0020 (8)	0.0051 (8)	0.0036 (8)

Geometric parameters (Å, º) top

N11—C12	1.328 (3)	C25—C26	1.388 (3)
N11—C16	1.341 (2)	C25—H25	0.95
N11—H11	0.88	C26—H26	0.95
C12—C13	1.384 (3)	O1—C1	1.291 (2)
C12—H12	0.95	O1—H1	0.84
C13—C14	1.393 (3)	O2—C1	1.229 (2)
C13—H13	0.95	O5—C2	1.417 (2)
C14—C15	1.386 (3)	O5—H5	0.84
C14—C24	1.487 (3)	O6—C3	1.411 (2)
C15—C16	1.380 (3)	O6—H6	0.84
C15—H15	0.95	O3—C4	1.307 (2)
C16—H16	0.95	O3—H3	0.84
N21—C22	1.330 (3)	O4—C4	1.218 (2)
N21—C26	1.333 (3)	C1—C2	1.523 (3)
C22—C23	1.390 (3)	C2—C3	1.538 (3)
C22—H22	0.95	C2—H2A	1.00
C23—C24	1.396 (3)	C3—C4	1.526 (3)
C23—H23	0.95	C3—H3A	1.00
C24—C25	1.390 (3)

C12—N11—C16	120.2 (2)	C26—C25—C24	119.4 (2)
C12—N11—H11	119.9	C26—C25—H25	120.3
C16—N11—H11	119.9	C24—C25—H25	120.3
N11—C12—C13	121.2 (2)	N21—C26—C25	123.1 (2)
N11—C12—H12	119.4	N21—C26—H26	118.5
C13—C12—H12	119.4	C25—C26—H26	118.5
C12—C13—C14	120.07 (19)	C1—O1—H1	109.5
C12—C13—H13	120.0	C2—O5—H5	109.5
C14—C13—H13	120.0	C3—O6—H6	109.5
C15—C14—C13	117.2 (2)	C4—O3—H3	109.5
C15—C14—C24	122.2 (2)	O2—C1—O1	125.9 (2)
C13—C14—C24	120.6 (2)	O2—C1—C2	120.1 (2)
C16—C15—C14	120.3 (2)	O1—C1—C2	114.1 (2)
C16—C15—H15	119.9	O5—C2—C1	112.0 (2)
C14—C15—H15	119.9	O5—C2—C3	109.4 (2)
N11—C16—C15	121.0 (2)	C1—C2—C3	109.9 (2)
N11—C16—H16	119.5	O5—C2—H2A	108.5
C15—C16—H16	119.5	C1—C2—H2A	108.5
C22—N21—C26	117.7 (2)	C3—C2—H2A	108.5
N21—C22—C23	123.3 (2)	O6—C3—C4	110.7 (2)
N21—C22—H22	118.4	O6—C3—C2	111.7 (2)
C23—C22—H22	118.4	C4—C3—C2	108.6 (2)
C22—C23—C24	119.0 (2)	O6—C3—H3A	108.6
C22—C23—H23	120.5	C4—C3—H3A	108.6
C24—C23—H23	120.5	C2—C3—H3A	108.6
C25—C24—C23	117.4 (2)	O4—C4—O3	124.8 (2)
C25—C24—C14	120.5 (2)	O4—C4—C3	120.0 (2)
C23—C24—C14	122.1 (2)	O3—C4—C3	115.2 (2)

C16—N11—C12—C13	−1.7 (3)	C23—C24—C25—C26	−1.0 (3)
N11—C12—C13—C14	−0.2 (3)	C14—C24—C25—C26	177.6 (2)
C12—C13—C14—C15	1.4 (3)	C22—N21—C26—C25	−0.2 (3)
C12—C13—C14—C24	−179.1 (2)	C24—C25—C26—N21	1.1 (3)
C13—C14—C15—C16	−0.9 (3)	O2—C1—C2—O5	11.4 (3)
C24—C14—C15—C16	179.6 (2)	O1—C1—C2—O5	−168.7 (2)
C12—N11—C16—C15	2.2 (3)	O2—C1—C2—C3	−110.4 (2)
C14—C15—C16—N11	−0.9 (4)	O1—C1—C2—C3	69.5 (2)
C26—N21—C22—C23	−0.9 (3)	O5—C2—C3—O6	−61.3 (2)
N21—C22—C23—C24	1.0 (3)	C1—C2—C3—O6	62.0 (2)
C22—C23—C24—C25	0.0 (3)	O5—C2—C3—C4	61.0 (2)
C22—C23—C24—C14	−178.6 (2)	C1—C2—C3—C4	−175.6 (2)
C15—C14—C24—C25	−162.4 (2)	O6—C3—C4—O4	−174.8 (2)
C13—C14—C24—C25	18.1 (3)	C2—C3—C4—O4	62.3 (2)
C15—C14—C24—C23	16.1 (3)	O6—C3—C4—O3	5.2 (2)
C13—C14—C24—C23	−163.4 (2)	C2—C3—C4—O3	−117.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O1	0.88	1.66	2.544 (2)	177
O1—H1···N11	0.84	1.71	2.544 (2)	175
O3—H3···N21ⁱ	0.84	1.78	2.614 (2)	174
O5—H5···O2ⁱⁱ	0.84	2.07	2.823 (2)	149
O5—H5···O2	0.84	2.22	2.693 (2)	116
O6—H6···O5ⁱⁱⁱ	0.84	1.90	2.740 (2)	173
C16—H16···O1^iv	0.95	2.36	3.279 (3)	164
C23—H23···O4^iv	0.95	2.50	3.448 (3)	175

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

(IV) 4,4'-Bipyridyl–(2R,3R)-tartaric acid (1/1) top

Crystal data top

C₁₄H₁₄N₂O₆	F(000) = 320
M_r = 306.27	D_x = 1.548 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 10.4430 (13) Å	Cell parameters from 1394 reflections
b = 4.4665 (6) Å	θ = 3.4–26.4°
c = 14.110 (2) Å	µ = 0.12 mm⁻¹
β = 92.954 (5)°	T = 150 K
V = 657.27 (15) Å³	Block, colourless
Z = 2	0.25 × 0.22 × 0.20 mm

Data collection top

Kappa-CCD diffractometer	1394 independent reflections
Radiation source: fine-focus sealed X-ray tube	1022 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
φ scans, and ω scans with κ offsets	θ_max = 26.4°, θ_min = 3.4°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→12
T_min = 0.970, T_max = 0.976	k = 0→5
1234567 measured reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.124	w = 1/[σ²(F_o²) + (0.0578P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
1394 reflections	Δρ_max = 0.23 e Å⁻³
204 parameters	Δρ_min = −0.24 e Å⁻³
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.030 (8)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.3114 (3)	0.5431 (7)	0.5344 (2)	0.0355 (8)
O2	0.1115 (3)	0.3951 (7)	0.4935 (2)	0.0362 (8)
O3	0.1755 (3)	0.1688 (7)	0.8691 (2)	0.0379 (8)
O4	0.3528 (3)	0.0004 (7)	0.8060 (2)	0.0371 (8)
O5	0.1167 (3)	0.0099 (7)	0.6305 (2)	0.0366 (8)
O6	0.1275 (3)	0.5255 (7)	0.7352 (2)	0.0350 (7)
C1	0.2101 (4)	0.3913 (10)	0.5436 (3)	0.0303 (10)
C2	0.2229 (4)	0.1921 (10)	0.6283 (3)	0.0295 (10)
C3	0.2369 (4)	0.3602 (10)	0.7219 (3)	0.0293 (10)
C4	0.2603 (4)	0.1584 (10)	0.8039 (3)	0.0295 (10)
N11	0.2947 (3)	0.8805 (9)	0.3949 (2)	0.0326 (9)
N21	0.2158 (3)	1.8094 (9)	0.0079 (3)	0.0367 (9)
C12	0.1804 (4)	0.9176 (11)	0.3511 (3)	0.0350 (11)
C13	0.1651 (4)	1.0992 (11)	0.2747 (3)	0.0354 (11)
C14	0.2681 (4)	1.2462 (10)	0.2432 (3)	0.0273 (10)
C15	0.3868 (4)	1.2039 (11)	0.2907 (3)	0.0349 (11)
C16	0.3960 (4)	1.0212 (11)	0.3666 (3)	0.0350 (10)
C22	0.3298 (5)	1.6972 (12)	0.0309 (3)	0.0449 (13)
C23	0.3520 (4)	1.5134 (12)	0.1065 (3)	0.0391 (11)
C24	0.2512 (4)	1.4399 (9)	0.1610 (3)	0.0290 (10)
C25	0.1326 (4)	1.5553 (11)	0.1364 (3)	0.0351 (11)
C26	0.1190 (4)	1.7399 (12)	0.0607 (3)	0.0369 (11)
H1	0.3022	0.6529	0.4862	0.053*	0.50
H3	0.1948	0.0431	0.9117	0.057*
H5	0.0702	0.0351	0.5808	0.055*
H6	0.1281	0.6806	0.7016	0.052*
H2A	0.3003	0.0630	0.6223	0.035*
H3A	0.3110	0.5010	0.7191	0.035*
H11	0.3027	0.7590	0.4439	0.039*	0.50
H12	0.1083	0.8151	0.3737	0.042*
H13	0.0830	1.1235	0.2435	0.042*
H15	0.4607	1.3032	0.2698	0.042*
H16	0.4765	0.9940	0.3999	0.042*
H22	0.3993	1.7470	−0.0070	0.054*
H23	0.4355	1.4371	0.1215	0.047*
H25	0.0608	1.5062	0.1721	0.042*
H26	0.0369	1.8228	0.0448	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0393 (17)	0.0355 (17)	0.0318 (16)	−0.0016 (16)	0.0013 (13)	0.0116 (15)
O2	0.0398 (17)	0.0328 (16)	0.0349 (16)	−0.0013 (15)	−0.0071 (14)	0.0026 (15)
O3	0.0453 (19)	0.0367 (19)	0.0324 (17)	0.0062 (15)	0.0084 (15)	0.0127 (14)
O4	0.0377 (17)	0.0388 (18)	0.0347 (16)	0.0089 (16)	0.0004 (13)	0.0094 (15)
O5	0.0409 (17)	0.0308 (17)	0.0369 (17)	−0.0070 (16)	−0.0089 (14)	0.0078 (15)
O6	0.0373 (16)	0.0288 (16)	0.0394 (17)	0.0075 (15)	0.0076 (13)	0.0074 (15)
C1	0.036 (2)	0.026 (2)	0.029 (2)	−0.001 (2)	0.004 (2)	0.003 (2)
C2	0.030 (2)	0.026 (2)	0.031 (2)	0.0005 (19)	−0.0030 (19)	0.004 (2)
C3	0.028 (2)	0.029 (2)	0.031 (2)	0.002 (2)	0.0013 (19)	0.006 (2)
C4	0.029 (2)	0.033 (2)	0.027 (2)	−0.002 (2)	0.0020 (19)	0.001 (2)
N11	0.037 (2)	0.0293 (19)	0.0313 (19)	−0.0015 (18)	0.0014 (17)	0.0051 (17)
N21	0.041 (2)	0.036 (2)	0.033 (2)	0.0002 (19)	0.0010 (18)	0.0045 (19)
C12	0.036 (2)	0.036 (3)	0.033 (2)	−0.004 (2)	0.001 (2)	0.004 (2)
C13	0.031 (2)	0.037 (3)	0.038 (3)	−0.003 (2)	−0.002 (2)	0.005 (2)
C14	0.028 (2)	0.028 (2)	0.025 (2)	0.0008 (19)	0.0012 (18)	0.0030 (19)
C15	0.034 (2)	0.036 (2)	0.034 (2)	−0.002 (2)	0.000 (2)	0.006 (2)
C16	0.038 (2)	0.032 (2)	0.034 (2)	−0.001 (2)	−0.005 (2)	0.007 (2)
C22	0.043 (3)	0.053 (3)	0.039 (3)	0.001 (3)	0.008 (2)	0.018 (3)
C23	0.035 (2)	0.044 (3)	0.038 (2)	0.006 (2)	0.005 (2)	0.011 (2)
C24	0.032 (2)	0.029 (2)	0.025 (2)	−0.0056 (19)	0.0023 (17)	0.0009 (19)
C25	0.034 (2)	0.035 (2)	0.036 (2)	−0.001 (2)	0.0002 (19)	0.011 (2)
C26	0.038 (3)	0.038 (3)	0.034 (2)	0.001 (2)	−0.003 (2)	0.008 (2)

Geometric parameters (Å, º) top

O1—C1	1.269 (5)	N21—C26	1.323 (5)
O1—H1	0.84	C12—C13	1.352 (6)
O2—C1	1.218 (5)	C12—H12	0.95
O3—C4	1.310 (5)	C13—C14	1.355 (6)
O3—H3	0.84	C13—H13	0.95
O4—C4	1.195 (5)	C14—C15	1.392 (6)
O5—C2	1.378 (5)	C14—C24	1.449 (6)
O5—H5	0.84	C15—C16	1.345 (6)
O6—C3	1.381 (5)	C15—H15	0.95
O6—H6	0.84	C16—H16	0.95
C1—C2	1.490 (6)	C22—C23	1.357 (6)
C2—C3	1.520 (6)	C22—H22	0.95
C2—H2A	1.00	C23—C24	1.375 (6)
C3—C4	1.477 (6)	C23—H23	0.95
C3—H3A	1.00	C24—C25	1.369 (6)
N11—C16	1.310 (6)	C25—C26	1.352 (6)
N11—C12	1.325 (5)	C25—H25	0.95
N11—H11	0.88	C26—H26	0.95
N21—C22	1.317 (6)

C1—O1—H1	109.5	C13—C12—H12	119.6
C4—O3—H3	109.5	C12—C13—C14	119.3 (4)
C2—O5—H5	109.5	C12—C13—H13	120.4
C3—O6—H6	109.5	C14—C13—H13	120.4
O2—C1—O1	128.1 (4)	C13—C14—C15	118.6 (4)
O2—C1—C2	120.8 (4)	C13—C14—C24	119.0 (4)
O1—C1—C2	111.1 (4)	C15—C14—C24	122.4 (4)
O5—C2—C1	109.4 (3)	C16—C15—C14	119.4 (4)
O5—C2—C3	108.2 (3)	C16—C15—H15	120.3
C1—C2—C3	113.7 (4)	C14—C15—H15	120.3
O5—C2—H2A	108.5	N11—C16—C15	120.5 (4)
C1—C2—H2A	108.5	N11—C16—H16	119.7
C3—C2—H2A	108.5	C15—C16—H16	119.7
O6—C3—C4	108.9 (3)	N21—C22—C23	122.7 (4)
O6—C3—C2	109.9 (3)	N21—C22—H22	118.6
C4—C3—C2	112.6 (3)	C23—C22—H22	118.6
O6—C3—H3A	108.5	C22—C23—C24	118.6 (4)
C4—C3—H3A	108.5	C22—C23—H23	120.7
C2—C3—H3A	108.5	C24—C23—H23	120.7
O4—C4—O3	125.3 (4)	C25—C24—C23	118.5 (4)
O4—C4—C3	118.7 (4)	C25—C24—C14	119.9 (4)
O3—C4—C3	116.0 (4)	C23—C24—C14	121.6 (4)
C16—N11—C12	121.3 (4)	C26—C25—C24	119.1 (4)
C16—N11—H11	119.3	C26—C25—H25	120.4
C12—N11—H11	119.3	C24—C25—H25	120.4
C22—N21—C26	118.6 (4)	N21—C26—C25	122.4 (4)
N11—C12—C13	120.9 (4)	N21—C26—H26	118.8
N11—C12—H12	119.6	C25—C26—H26	118.8

O2—C1—C2—O5	6.2 (5)	C13—C14—C15—C16	−0.4 (7)
O1—C1—C2—O5	−174.0 (4)	C24—C14—C15—C16	179.9 (4)
O2—C1—C2—C3	−114.9 (4)	C12—N11—C16—C15	−1.2 (7)
O1—C1—C2—C3	64.8 (5)	C14—C15—C16—N11	1.0 (7)
O5—C2—C3—O6	−58.5 (4)	C26—N21—C22—C23	0.0 (8)
C1—C2—C3—O6	63.2 (5)	N21—C22—C23—C24	0.4 (8)
O5—C2—C3—C4	63.0 (4)	C22—C23—C24—C25	0.1 (7)
C1—C2—C3—C4	−175.2 (3)	C22—C23—C24—C14	−179.6 (5)
O6—C3—C4—O4	−178.6 (4)	C13—C14—C24—C25	22.6 (6)
C2—C3—C4—O4	59.3 (5)	C15—C14—C24—C25	−157.8 (4)
O6—C3—C4—O3	1.5 (5)	C13—C14—C24—C23	−157.6 (4)
C2—C3—C4—O3	−120.6 (4)	C15—C14—C24—C23	22.0 (6)
C16—N11—C12—C13	1.0 (7)	C23—C24—C25—C26	−1.0 (7)
N11—C12—C13—C14	−0.4 (7)	C14—C24—C25—C26	178.8 (4)
C12—C13—C14—C15	0.2 (7)	C22—N21—C26—C25	−0.9 (7)
C12—C13—C14—C24	179.8 (4)	C24—C25—C26—N21	1.4 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O1	0.88	1.60	2.479 (5)	178
O1—H1···N11	0.84	1.64	2.479 (5)	176
O3—H3···N21ⁱ	0.84	1.72	2.550 (4)	171
O5—H5···O2	0.84	2.08	2.586 (4)	118
O5—H5···O2ⁱⁱ	0.84	2.21	2.929 (4)	144
O6—H6···O5ⁱⁱⁱ	0.84	1.78	2.619 (4)	176
C15—H15···O4^iv	0.95	2.43	3.375 (5)	170
C23—H23···O4^iv	0.95	2.40	3.262 (5)	150

Symmetry codes: (i) x, y−2, z+1; (ii) −x, y−1/2, −z+1; (iii) x, y+1, z; (iv) −x+1, y+3/2, −z+1.

(V) Piperazine–(2R,3R)-tartaric acid (1/1) top

Crystal data top

C₄H₁₂N₂·C₄H₄O₆	F(000) = 252
M_r = 236.23	D_x = 1.521 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 6.4043 (3) Å	Cell parameters from 1118 reflections
b = 9.0860 (5) Å	θ = 3.2–27.5°
c = 9.3734 (4) Å	µ = 0.13 mm⁻¹
β = 109.006 (3)°	T = 150 K
V = 515.70 (4) Å³	Needle, colourless
Z = 2	0.28 × 0.10 × 0.08 mm

Data collection top

Kappa-CCD diffractometer	1241 independent reflections
Radiation source: fine-focus sealed X-ray tube	1061 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
φ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→8
T_min = 0.964, T_max = 0.990	k = 0→11
3749 measured reflections	l = −12→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.088	w = 1/[σ²(F_o²) + (0.0293P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
1241 reflections	Δρ_max = 0.19 e Å⁻³
148 parameters	Δρ_min = −0.18 e Å⁻³
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.057 (18)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N11	0.6752 (3)	0.4588 (3)	0.6733 (2)	0.0218 (5)
N14	0.3480 (3)	0.5406 (3)	0.8060 (2)	0.0203 (5)
C12	0.5186 (4)	0.3465 (4)	0.6953 (3)	0.0231 (6)
C13	0.4443 (4)	0.3900 (3)	0.8269 (3)	0.0223 (6)
C15	0.5076 (4)	0.6521 (3)	0.7870 (3)	0.0233 (6)
C16	0.5784 (4)	0.6098 (3)	0.6534 (3)	0.0232 (6)
O1	1.0097 (3)	0.4036 (2)	−0.05976 (19)	0.0243 (5)
O2	1.2387 (3)	0.5818 (2)	0.06616 (18)	0.0242 (5)
O3	1.0608 (3)	0.4915 (3)	0.5164 (2)	0.0334 (5)
O4	0.7004 (3)	0.4618 (3)	0.39278 (19)	0.0276 (5)
O5	0.9700 (3)	0.2861 (2)	0.1863 (2)	0.0231 (4)
O6	0.7233 (3)	0.5573 (2)	0.13543 (18)	0.0243 (5)
C1	1.1092 (4)	0.4756 (3)	0.0577 (3)	0.0190 (5)
C2	1.0706 (4)	0.4270 (3)	0.2039 (3)	0.0191 (6)
C3	0.9288 (4)	0.5406 (3)	0.2516 (3)	0.0198 (5)
C4	0.8949 (4)	0.4936 (3)	0.4004 (3)	0.0220 (6)
H11A	0.7130	0.4344	0.5896	0.026*
H11B	0.8020	0.4580	0.7556	0.026*
H14A	0.3072	0.5650	0.8885	0.024*
H14B	0.2232	0.5416	0.7223	0.024*
H12A	0.5920	0.2492	0.7150	0.028*
H12B	0.3889	0.3388	0.6026	0.028*
H13A	0.3327	0.3188	0.8366	0.027*
H13B	0.5720	0.3867	0.9212	0.027*
H15A	0.6382	0.6565	0.8795	0.028*
H15B	0.4374	0.7505	0.7701	0.028*
H16A	0.4492	0.6133	0.5601	0.028*
H16B	0.6891	0.6812	0.6428	0.028*
H2	1.2171	0.4207	0.2853	0.023*
H3	1.0075	0.6373	0.2678	0.024*
H5	0.9205	0.2647	0.0942	0.035*
H6	0.6203	0.5382	0.1696	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N11	0.0205 (10)	0.0287 (14)	0.0179 (9)	0.0003 (9)	0.0089 (8)	−0.0012 (10)
N14	0.0210 (9)	0.0212 (13)	0.0197 (10)	−0.0007 (9)	0.0081 (8)	0.0003 (9)
C12	0.0273 (12)	0.0206 (14)	0.0229 (12)	0.0005 (11)	0.0101 (10)	−0.0017 (11)
C13	0.0246 (12)	0.0198 (15)	0.0237 (13)	0.0009 (11)	0.0096 (10)	0.0016 (12)
C15	0.0258 (12)	0.0207 (16)	0.0248 (13)	−0.0007 (11)	0.0101 (10)	−0.0013 (11)
C16	0.0221 (12)	0.0277 (17)	0.0195 (11)	−0.0052 (11)	0.0064 (10)	−0.0002 (11)
O1	0.0252 (9)	0.0284 (12)	0.0197 (8)	−0.0009 (8)	0.0079 (7)	−0.0019 (8)
O2	0.0267 (9)	0.0254 (12)	0.0231 (8)	−0.0031 (8)	0.0117 (7)	−0.0008 (8)
O3	0.0275 (10)	0.0515 (16)	0.0189 (9)	0.0023 (10)	0.0046 (7)	−0.0008 (9)
O4	0.0251 (9)	0.0388 (13)	0.0216 (9)	−0.0039 (9)	0.0113 (7)	−0.0003 (9)
O5	0.0290 (9)	0.0197 (10)	0.0218 (9)	−0.0021 (8)	0.0100 (8)	−0.0005 (8)
O6	0.0207 (8)	0.0321 (12)	0.0205 (8)	0.0030 (8)	0.0072 (7)	0.0021 (8)
C1	0.0166 (11)	0.0203 (14)	0.0206 (12)	0.0022 (10)	0.0068 (9)	−0.0012 (11)
C2	0.0181 (11)	0.0189 (15)	0.0202 (11)	0.0005 (10)	0.0061 (9)	−0.0006 (10)
C3	0.0184 (10)	0.0211 (14)	0.0199 (11)	0.0002 (10)	0.0062 (9)	−0.0021 (11)
C4	0.0249 (12)	0.0236 (16)	0.0177 (11)	0.0013 (12)	0.0072 (10)	−0.0019 (11)

Geometric parameters (Å, º) top

N11—C12	1.491 (4)	C16—H16A	0.99
N11—C16	1.492 (4)	C16—H16B	0.99
N11—H11A	0.92	O1—C1	1.261 (3)
N11—H11B	0.92	O2—C1	1.258 (3)
N14—C13	1.487 (4)	O3—C4	1.249 (3)
N14—C15	1.491 (3)	O4—C4	1.258 (3)
N14—H14A	0.92	O5—C2	1.419 (3)
N14—H14B	0.92	O5—H5	0.84
C12—C13	1.512 (3)	O6—C3	1.416 (3)
C12—H12A	0.99	O6—H6	0.84
C12—H12B	0.99	C1—C2	1.535 (3)
C13—H13A	0.99	C2—C3	1.534 (4)
C13—H13B	0.99	C2—H2	1.00
C15—C16	1.514 (3)	C3—C4	1.541 (3)
C15—H15A	0.99	C3—H3	1.00
C15—H15B	0.99

C12—N11—C16	112.1 (2)	C16—C15—H15B	109.9
C12—N11—H11A	109.2	H15A—C15—H15B	108.3
C16—N11—H11A	109.2	N11—C16—C15	110.8 (2)
C12—N11—H11B	109.2	N11—C16—H16A	109.5
C16—N11—H11B	109.2	C15—C16—H16A	109.5
H11A—N11—H11B	107.9	N11—C16—H16B	109.5
C13—N14—C15	111.7 (2)	C15—C16—H16B	109.5
C13—N14—H14A	109.3	H16A—C16—H16B	108.1
C15—N14—H14A	109.3	C2—O5—H5	109.5
C13—N14—H14B	109.3	C3—O6—H6	109.5
C15—N14—H14B	109.3	O2—C1—O1	126.1 (2)
H14A—N14—H14B	107.9	O2—C1—C2	117.3 (2)
N11—C12—C13	109.8 (2)	O1—C1—C2	116.6 (2)
N11—C12—H12A	109.7	O5—C2—C3	110.6 (2)
C13—C12—H12A	109.7	O5—C2—C1	110.8 (2)
N11—C12—H12B	109.7	C3—C2—C1	110.5 (2)
C13—C12—H12B	109.7	O5—C2—H2	108.3
H12A—C12—H12B	108.2	C3—C2—H2	108.3
N14—C13—C12	111.1 (2)	C1—C2—H2	108.3
N14—C13—H13A	109.4	O6—C3—C2	109.8 (2)
C12—C13—H13A	109.4	O6—C3—C4	110.9 (2)
N14—C13—H13B	109.4	C2—C3—C4	110.4 (2)
C12—C13—H13B	109.4	O6—C3—H3	108.6
H13A—C13—H13B	108.0	C2—C3—H3	108.6
N14—C15—C16	109.1 (2)	C4—C3—H3	108.6
N14—C15—H15A	109.9	O3—C4—O4	126.3 (2)
C16—C15—H15A	109.9	O3—C4—C3	117.5 (2)
N14—C15—H15B	109.9	O4—C4—C3	116.2 (2)

C16—N11—C12—C13	−55.5 (3)	O1—C1—C2—C3	−108.7 (3)
C15—N14—C13—C12	−57.7 (3)	O5—C2—C3—O6	−64.1 (2)
N11—C12—C13—N14	55.2 (3)	C1—C2—C3—O6	58.9 (3)
C13—N14—C15—C16	57.7 (3)	O5—C2—C3—C4	58.4 (3)
C12—N11—C16—C15	57.2 (3)	C1—C2—C3—C4	−178.6 (2)
N14—C15—C16—N11	−56.9 (3)	O6—C3—C4—O3	−171.9 (2)
O2—C1—C2—O5	−164.9 (2)	C2—C3—C4—O3	66.2 (3)
O1—C1—C2—O5	14.2 (3)	O6—C3—C4—O4	7.8 (4)
O2—C1—C2—C3	72.2 (3)	C2—C3—C4—O4	−114.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11B···O1ⁱ	0.92	1.87	2.759 (3)	161
N11—H11A···O4	0.92	1.84	2.686 (2)	152
N14—H14A···O2ⁱⁱ	0.92	1.86	2.773 (2)	170
N14—H14B···O3ⁱⁱⁱ	0.92	1.93	2.775 (3)	153
O5—H5···O1	0.84	2.13	2.628 (3)	118
O5—H5···O2^iv	0.84	2.25	2.962 (3)	143
O6—H6···O4	0.84	2.10	2.613 (2)	119
O6—H6···O2ⁱⁱⁱ	0.84	2.35	2.965 (2)	130

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

(VI) Piperazine–racemic tartaric acid (1/2) top

Crystal data top

C₄H₁₂N₂·2(C₄H₅O₆)	F(000) = 408
M_r = 386.32	D_x = 1.653 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.5439 (3) Å	Cell parameters from 1794 reflections
b = 15.7915 (8) Å	θ = 2.6–27.5°
c = 7.5357 (4) Å	µ = 0.15 mm⁻¹
β = 94.484 (2)°	T = 150 K
V = 776.34 (7) Å³	Plate, colourless
Z = 2	0.24 × 0.22 × 0.08 mm

Data collection top

Kappa-CCD diffractometer	1776 independent reflections
Radiation source: fine-focus sealed X-ray tube	1252 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
φ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 2.6°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→8
T_min = 0.965, T_max = 0.988	k = 0→20
6672 measured reflections	l = −9→9

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0756P)²] where P = (F_o² + 2F_c²)/3
1776 reflections	(Δ/σ)_max < 0.001
121 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Special details top

Geometry. Mean-plane data from the final SHELXL97 refinement run:-

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

6.3814 (0.0015) x + 2.7093 (0.0144) y - 1.6269 (0.0079) z = 1.8142 (0.0093)

* 0.0054 (0.0016) C1 * -0.0015 (0.0005) C2 * -0.0018 (0.0005) O1 * -0.0021 (0.0006) O2

Rms deviation of fitted atoms = 0.0031

1.2416 (0.0157) x + 14.8739 (0.0047) y - 2.1943 (0.0085) z = 9.8140 (0.0043)

Angle to previous plane (with approximate e.s.d.) = 67.33 (15)

* 0.0039 (0.0011) C1 * -0.0039 (0.0010) C2 * -0.0040 (0.0011) C3 * 0.0039 (0.0011) C4

Rms deviation of fitted atoms = 0.0039

- 5.9072 (0.0026) x + 6.7673 (0.0134) y + 0.2429 (0.0076) z = 5.8433 (0.0098)

Angle to previous plane (with approximate e.s.d.) = 75.93 (14)

* -0.0012 (0.0004) C3 * 0.0045 (0.0016) C4 * -0.0016 (0.0006) O3 * -0.0016 (0.0006) O4

Rms deviation of fitted atoms = 0.0026

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	−0.0820 (2)	0.70392 (9)	−0.26361 (19)	0.0189 (4)
O2	−0.0115 (2)	0.56612 (10)	−0.21608 (19)	0.0212 (4)
O3	−0.2094 (2)	0.66547 (9)	0.41691 (18)	0.0185 (4)
O4	−0.0736 (2)	0.78731 (9)	0.32579 (19)	0.0203 (4)
O5	0.1053 (2)	0.59686 (9)	0.13482 (19)	0.0192 (4)
O6	−0.3419 (2)	0.62559 (9)	0.07477 (18)	0.0167 (4)
C1	−0.0273 (3)	0.63842 (14)	−0.1623 (3)	0.0161 (5)
C2	0.0107 (3)	0.66347 (13)	0.0326 (3)	0.0159 (5)
C3	−0.1934 (3)	0.69076 (13)	0.1021 (3)	0.0153 (5)
C4	−0.1563 (3)	0.71703 (13)	0.2976 (3)	0.0153 (5)
N1	0.4486 (3)	0.55942 (11)	0.3602 (2)	0.0173 (4)
C12	0.5315 (3)	0.47449 (13)	0.3193 (3)	0.0182 (5)
C13	0.6681 (3)	0.44324 (14)	0.4768 (3)	0.0191 (5)
H1	−0.1223	0.6869	−0.3661	0.028*
H5	0.0338	0.5528	0.1212	0.029*
H6	−0.4356	0.6417	−0.0001	0.025*
H2	0.1053	0.7133	0.0400	0.019*
H3	−0.2443	0.7415	0.0325	0.018*
H1A	0.3635	0.5778	0.2651	0.021*
H1B	0.5550	0.5974	0.3774	0.021*
H12A	0.6110	0.4781	0.2131	0.022*
H12B	0.4172	0.4342	0.2931	0.022*
H13A	0.7195	0.3859	0.4514	0.023*
H13B	0.7876	0.4814	0.4974	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0225 (8)	0.0215 (8)	0.0125 (8)	0.0003 (6)	−0.0011 (6)	−0.0002 (6)
O2	0.0267 (9)	0.0185 (9)	0.0185 (8)	0.0010 (6)	0.0024 (6)	−0.0014 (6)
O3	0.0228 (8)	0.0208 (8)	0.0114 (7)	−0.0023 (6)	−0.0005 (6)	0.0017 (6)
O4	0.0212 (8)	0.0217 (9)	0.0178 (8)	−0.0052 (6)	−0.0003 (6)	−0.0025 (6)
O5	0.0181 (8)	0.0196 (8)	0.0192 (8)	0.0008 (6)	−0.0036 (6)	0.0044 (6)
O6	0.0156 (7)	0.0191 (8)	0.0148 (8)	−0.0032 (6)	−0.0025 (5)	0.0009 (6)
C1	0.0124 (10)	0.0196 (11)	0.0167 (11)	−0.0019 (8)	0.0035 (7)	0.0007 (8)
C2	0.0158 (10)	0.0159 (10)	0.0157 (10)	0.0006 (8)	0.0001 (8)	0.0017 (8)
C3	0.0161 (10)	0.0149 (10)	0.0145 (10)	−0.0013 (8)	−0.0011 (8)	0.0006 (8)
C4	0.0134 (10)	0.0187 (11)	0.0134 (10)	0.0024 (8)	−0.0006 (7)	−0.0009 (8)
N1	0.0169 (9)	0.0191 (10)	0.0159 (9)	0.0015 (7)	0.0003 (7)	0.0018 (7)
C12	0.0206 (10)	0.0189 (11)	0.0153 (11)	0.0007 (8)	0.0023 (8)	−0.0009 (8)
C13	0.0183 (10)	0.0204 (11)	0.0190 (11)	0.0028 (8)	0.0045 (8)	0.0011 (9)

Geometric parameters (Å, º) top

O1—C1	1.319 (2)	C3—C4	1.532 (3)
O1—H1	0.84	C3—H3	1.00
O2—C1	1.219 (3)	N1—C12	1.488 (3)
O3—C4	1.281 (2)	N1—C13ⁱ	1.497 (3)
O4—C4	1.246 (3)	N1—H1A	0.92
O5—C2	1.417 (2)	N1—H1B	0.92
O5—H5	0.84	C12—C13	1.512 (3)
O6—C3	1.419 (2)	C12—H12A	0.99
O6—H6	0.84	C12—H12B	0.99
C1—C2	1.523 (3)	C13—N1ⁱ	1.497 (3)
C2—C3	1.534 (3)	C13—H13A	0.99
C2—H2	1.00	C13—H13B	0.99

C1—O1—H1	109.5	O3—C4—C3	118.1 (2)
C2—O5—H5	109.5	C12—N1—C13ⁱ	111.2 (2)
C3—O6—H6	109.5	C12—N1—H1A	109.4
O2—C1—O1	124.6 (2)	C13ⁱ—N1—H1A	109.4
O2—C1—C2	123.6 (2)	C12—N1—H1B	109.4
O1—C1—C2	111.8 (2)	C13ⁱ—N1—H1B	109.4
O5—C2—C1	111.3 (2)	H1A—N1—H1B	108.0
O5—C2—C3	112.2 (2)	N1—C12—C13	109.5 (2)
C1—C2—C3	108.8 (2)	N1—C12—H12A	109.8
O5—C2—H2	108.2	C13—C12—H12A	109.8
C1—C2—H2	108.2	N1—C12—H12B	109.8
C3—C2—H2	108.2	C13—C12—H12B	109.8
O6—C3—C4	113.1 (2)	H12A—C12—H12B	108.2
O6—C3—C2	110.6 (2)	N1ⁱ—C13—C12	110.2 (2)
C4—C3—C2	109.1 (2)	N1ⁱ—C13—H13A	109.6
O6—C3—H3	108.0	C12—C13—H13A	109.6
C4—C3—H3	108.0	N1ⁱ—C13—H13B	109.6
C2—C3—H3	108.0	C12—C13—H13B	109.6
O4—C4—O3	125.8 (2)	H13A—C13—H13B	108.1
O4—C4—C3	116.1 (2)

O2—C1—C2—O5	11.9 (3)	C1—C2—C3—C4	−179.4 (2)
O1—C1—C2—O5	−169.1 (2)	O6—C3—C4—O4	−161.1 (2)
O2—C1—C2—C3	−112.2 (2)	C2—C3—C4—O4	75.4 (2)
O1—C1—C2—C3	66.8 (2)	O6—C3—C4—O3	19.7 (2)
O5—C2—C3—O6	−67.8 (2)	C2—C3—C4—O3	−103.7 (2)
C1—C2—C3—O6	55.7 (2)	C13ⁱ—N1—C12—C13	−57.9 (2)
O5—C2—C3—C4	57.1 (2)	N1—C12—C13—N1ⁱ	57.3 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3ⁱⁱ	0.84	1.72	2.558 (2)	173
O5—H5···O2ⁱⁱⁱ	0.84	2.02	2.727 (2)	142
O6—H6···O4^iv	0.84	1.90	2.696 (2)	158
N1—H1B···O3^v	0.92	1.88	2.801 (2)	174
N1—H1A···O5	0.92	1.91	2.772 (2)	155

Symmetry codes: (ii) x, y, z−1; (iii) −x, −y+1, −z; (iv) x−1/2, −y+3/2, z−1/2; (v) x+1, y, z.

(VII) 1,4-Diazabicyclo[2.2.2]octane–racemic tartaric acid (1/2) top

Crystal data top

(C₆H₁₃N₂)·2(C₄H_5.5O₆)	F(000) = 436
M_r = 412.35	D_x = 1.560 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.3240 (1) Å	Cell parameters from 2029 reflections
b = 15.9935 (3) Å	θ = 3.0–27.4°
c = 7.5149 (1) Å	µ = 0.14 mm⁻¹
β = 94.4050 (11)°	T = 150 K
V = 877.67 (2) Å³	Block, colourless
Z = 2	0.38 × 0.35 × 0.32 mm

Data collection top

Kappa-CCD diffractometer	1991 independent reflections
Radiation source: fine-focus sealed X-ray tube	1756 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
φ scans, and ω scans with κ offsets	θ_max = 27.4°, θ_min = 3.0°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→9
T_min = 0.950, T_max = 0.957	k = 0→20
8773 measured reflections	l = −9→9

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0365P)² + 0.3876P] where P = (F_o² + 2F_c²)/3
1991 reflections	(Δ/σ)_max = 0.001
162 parameters	Δρ_max = 0.30 e Å⁻³
9 restraints	Δρ_min = −0.30 e Å⁻³

Special details top

Geometry. Mean-plane data from the final SHELXL97 refinement run:-

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 7.1870 (0.0010) x + 2.4068 (0.0125) y + 1.4661 (0.0052) z = 3.2416 (0.0092)

* 0.0012 (0.0012) C1 * -0.0003 (0.0003) C2 * -0.0004 (0.0004) O1 * -0.0005 (0.0005) O2

Rms deviation of fitted atoms = 0.0007

- 2.0482 (0.0100) x + 14.7873 (0.0045) y + 2.0999 (0.0049) z = 11.8786 (0.0066)

Angle to previous plane (with approximate e.s.d.) = 63.60 (10)

* 0.0250 (0.0006) C1 * -0.0259 (0.0006) C2 * -0.0236 (0.0006) C3 * 0.0245 (0.0006) C4

Rms deviation of fitted atoms = 0.0248

6.4202 (0.0022) x + 7.6965 (0.0087) y - 0.5111 (0.0050) z = 5.8277 (0.0068)

Angle to previous plane (with approximate e.s.d.) = 78.49 (8)

* -0.0019 (0.0003) C3 * 0.0070 (0.0010) C4 * -0.0025 (0.0004) O3 * -0.0026 (0.0004) O4

Rms deviation of fitted atoms = 0.0041

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.3866 (6)	0.5503 (3)	0.5390 (4)	0.0193 (6)	0.50
C11	0.5731 (3)	0.56561 (16)	0.6266 (3)	0.0240 (5)	0.50
C12	0.3825 (3)	0.56567 (15)	0.3427 (3)	0.0225 (5)	0.50
C13	0.3285 (3)	0.46297 (15)	0.5725 (4)	0.0250 (5)	0.50
C21	0.7112 (3)	0.51351 (16)	0.5304 (4)	0.0213 (5)	0.50
C22	0.5060 (3)	0.50157 (15)	0.2591 (3)	0.0202 (5)	0.50
C23	0.4744 (3)	0.40468 (15)	0.5061 (3)	0.0236 (5)	0.50
N2	0.6066 (5)	0.4545 (2)	0.4073 (4)	0.0193 (6)	0.50
O1	0.03402 (14)	0.71219 (6)	1.20838 (11)	0.0272 (2)
O2	−0.01999 (19)	0.57534 (6)	1.16823 (13)	0.0435 (3)
O3	0.13914 (12)	0.67580 (6)	0.52707 (11)	0.0237 (2)
O4	0.00622 (13)	0.79264 (6)	0.61703 (12)	0.0273 (2)
O5	−0.10384 (13)	0.59470 (6)	0.81670 (12)	0.0249 (2)
O6	0.27340 (12)	0.63911 (5)	0.86094 (12)	0.0228 (2)
C1	−0.0082 (2)	0.64607 (8)	1.11104 (16)	0.0262 (3)
C2	−0.04163 (17)	0.66609 (8)	0.91325 (15)	0.0210 (3)
C3	0.13421 (16)	0.70084 (7)	0.84113 (15)	0.0185 (3)
C4	0.09017 (15)	0.72576 (7)	0.64564 (15)	0.0177 (2)
H1A	0.3048	0.5867	0.5876	0.023*	0.50
H11A	0.5771	0.5494	0.7540	0.029*	0.50
H11B	0.6040	0.6257	0.6198	0.029*	0.50
H12A	0.4263	0.6230	0.3201	0.027*	0.50
H12B	0.2555	0.5604	0.2885	0.027*	0.50
H13A	0.2081	0.4516	0.5079	0.030*	0.50
H13B	0.3173	0.4542	0.7016	0.030*	0.50
H21A	0.7884	0.5506	0.4619	0.026*	0.50
H21B	0.7919	0.4820	0.6183	0.026*	0.50
H22A	0.4311	0.4627	0.1812	0.024*	0.50
H22B	0.5936	0.5303	0.1860	0.024*	0.50
H23A	0.5402	0.3760	0.6087	0.028*	0.50
H23B	0.4155	0.3616	0.4262	0.028*	0.50
H2A	0.6886	0.4181	0.3591	0.023*	0.50
H1	0.0617	0.6975	1.3143	0.041*
H5	−0.0448	0.5526	0.8555	0.037*
H6	0.3602	0.6569	0.9302	0.034*
H2	−0.1387	0.7101	0.8987	0.025*
H3	0.1746	0.7515	0.9115	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0190 (6)	0.0192 (7)	0.0198 (19)	0.0024 (5)	0.0030 (11)	−0.0024 (11)
C11	0.0213 (12)	0.0245 (13)	0.0256 (13)	0.0007 (10)	−0.0017 (10)	−0.0092 (10)
C12	0.0254 (12)	0.0224 (12)	0.0194 (11)	0.0049 (10)	0.0005 (9)	0.0052 (9)
C13	0.0245 (13)	0.0256 (13)	0.0258 (14)	−0.0032 (10)	0.0085 (11)	0.0036 (11)
C21	0.0179 (11)	0.0235 (12)	0.0221 (13)	0.0013 (9)	−0.0019 (9)	−0.0046 (11)
C22	0.0207 (11)	0.0255 (13)	0.0146 (10)	0.0008 (9)	0.0017 (8)	0.0014 (9)
C23	0.0323 (13)	0.0164 (12)	0.0225 (12)	−0.0038 (10)	0.0050 (10)	0.0017 (9)
N2	0.0190 (6)	0.0192 (7)	0.0198 (19)	0.0024 (5)	0.0030 (11)	−0.0024 (11)
O1	0.0468 (6)	0.0218 (5)	0.0129 (4)	0.0050 (4)	0.0026 (4)	0.0001 (3)
O2	0.0892 (9)	0.0217 (5)	0.0191 (5)	0.0035 (5)	0.0001 (5)	0.0033 (4)
O3	0.0304 (5)	0.0269 (5)	0.0139 (4)	0.0064 (4)	0.0026 (3)	−0.0025 (3)
O4	0.0365 (5)	0.0262 (5)	0.0184 (4)	0.0117 (4)	−0.0021 (4)	0.0020 (3)
O5	0.0290 (5)	0.0246 (5)	0.0206 (4)	−0.0008 (4)	−0.0020 (3)	−0.0007 (4)
O6	0.0227 (4)	0.0202 (5)	0.0238 (5)	0.0045 (3)	−0.0089 (3)	−0.0028 (3)
C1	0.0414 (7)	0.0216 (6)	0.0159 (6)	0.0069 (5)	0.0049 (5)	0.0005 (5)
C2	0.0285 (6)	0.0208 (6)	0.0138 (5)	0.0052 (5)	0.0015 (4)	−0.0003 (4)
C3	0.0250 (6)	0.0162 (5)	0.0135 (5)	0.0047 (4)	−0.0032 (4)	−0.0021 (4)
C4	0.0179 (5)	0.0207 (6)	0.0143 (5)	0.0007 (4)	−0.0003 (4)	−0.0002 (4)

Geometric parameters (Å, º) top

N1—C11	1.490 (3)	C22—H22A	0.99
N1—C12	1.493 (3)	C22—H22B	0.99
N1—C13	1.488 (3)	C23—H23A	0.99
N2—C21	1.491 (3)	C23—H23B	0.99
N2—C22	1.491 (3)	O1—C1	1.309 (2)
N2—C23	1.495 (3)	O1—H1	0.84
N1—H1A	0.93	O2—C1	1.216 (2)
N2—H2A	0.93	O3—C4	1.269 (2)
C11—C21	1.534 (3)	O4—C4	1.244 (2)
C11—H11A	0.99	O5—C2	1.410 (2)
C11—H11B	0.99	O5—H5	0.84
C12—C22	1.533 (3)	O6—C3	1.419 (2)
C12—H12A	0.99	O6—H6	0.84
C12—H12B	0.99	C1—C2	1.522 (2)
C13—C23	1.531 (3)	C2—C3	1.539 (2)
C13—H13A	0.99	C2—H2	1.00
C13—H13B	0.99	C3—C4	1.532 (2)
C21—H21A	0.99	C3—H3	1.00
C21—H21B	0.99

C13—N1—C11	110.1 (3)	H21A—C21—H21B	108.4
C13—N1—C12	109.7 (3)	N2—C22—C12	107.7 (3)
C11—N1—C12	110.9 (3)	N2—C22—H22A	110.2
C13—N1—H1A	108.7	C12—C22—H22A	110.2
C11—N1—H1A	108.7	N2—C22—H22B	110.2
C12—N1—H1A	108.7	C12—C22—H22B	110.2
C21—N2—C22	110.2 (3)	H22A—C22—H22B	108.5
C21—N2—C23	110.6 (3)	N2—C23—C13	109.4 (3)
C22—N2—C23	109.8 (3)	N2—C23—H23A	109.8
C21—N2—H2A	108.8	C13—C23—H23A	109.8
C22—N2—H2A	108.8	N2—C23—H23B	109.8
C23—N2—H2A	108.8	C13—C23—H23B	109.8
N1—C11—C21	108.5 (3)	H23A—C23—H23B	108.2
N1—C11—H11A	110.0	C1—O1—H1	109.5
C21—C11—H11A	110.0	C2—O5—H5	109.5
N1—C11—H11B	110.0	C3—O6—H6	109.5
C21—C11—H11B	110.0	O2—C1—O1	125.1 (2)
H11A—C11—H11B	108.4	O2—C1—C2	122.1 (2)
N1—C12—C22	109.1 (3)	O1—C1—C2	112.9 (2)
N1—C12—H12A	109.9	O5—C2—C1	110.7 (2)
C22—C12—H12A	109.9	O5—C2—C3	110.94 (9)
N1—C12—H12B	109.9	C1—C2—C3	110.1 (2)
C22—C12—H12B	109.9	O5—C2—H2	108.3
H12A—C12—H12B	108.3	C1—C2—H2	108.3
N1—C13—C23	107.5 (3)	C3—C2—H2	108.3
N1—C13—H13A	110.2	O6—C3—C4	112.22 (9)
C23—C13—H13A	110.2	O6—C3—C2	109.01 (9)
N1—C13—H13B	110.2	C4—C3—C2	108.14 (9)
C23—C13—H13B	110.2	O6—C3—H3	109.1
H13A—C13—H13B	108.5	C4—C3—H3	109.1
N2—C21—C11	108.1 (3)	C2—C3—H3	109.1
N2—C21—H21A	110.1	O3—C4—O4	125.6 (2)
C11—C21—H21A	110.1	O3—C4—C3	117.4 (2)
N2—C21—H21B	110.1	O4—C4—C3	117.0 (2)
C11—C21—H21B	110.1

C13—N1—C11—C21	68.1 (3)	C13—C23—N2—C22	−56.2 (3)
C12—N1—C11—C21	−53.5 (4)	O2—C1—C2—O5	5.98 (19)
C13—N1—C12—C22	−57.1 (3)	O1—C1—C2—O5	−174.3 (2)
C11—N1—C12—C22	64.8 (3)	O2—C1—C2—C3	−117.1 (2)
C11—N1—C13—C23	−56.2 (3)	O1—C1—C2—C3	62.7 (2)
C12—N1—C13—C23	66.2 (3)	O5—C2—C3—O6	−61.2 (2)
N1—C11—C21—N2	−10.5 (3)	C1—C2—C3—O6	61.7 (2)
N1—C12—C22—N2	−7.9 (3)	O5—C2—C3—C4	61.0 (2)
N1—C13—C23—N2	−8.5 (3)	C1—C2—C3—C4	−176.1 (2)
C11—C21—N2—C22	68.0 (3)	O6—C3—C4—O3	18.9 (2)
C11—C21—N2—C23	−53.5 (4)	C2—C3—C4—O3	−101.4 (2)
C12—C22—N2—C21	−56.7 (3)	O6—C3—C4—O4	−162.4 (2)
C12—C22—N2—C23	65.3 (3)	C2—C3—C4—O4	77.3 (2)
C13—C23—N2—C21	65.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.93	1.90	2.701 (5)	142
N1—H1A···O6	0.93	2.25	2.977 (4)	135
N2—H2A···O6ⁱ	0.93	1.93	2.711 (5)	141
N2—H2A···O3ⁱ	0.93	2.10	2.813 (5)	132
O1—H1···O3ⁱⁱ	0.84	1.69	2.527 (2)	173
O5—H5···O2ⁱⁱⁱ	0.84	2.11	2.866 (2)	149
O6—H6···O4^iv	0.84	1.88	2.702 (2)	166

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z+1; (iii) −x, −y+1, −z+2; (iv) x+1/2, −y+3/2, z+1/2.

(VIII) 1,4-Diazabicyclo[2.2.2]octane–(2R,3R)-tartaric acid (3/4) top

Crystal data top

2(C₆H₁₄N₂)·C₆H₁₃N₂·3(C₄H₅O₆)·C₄H₄O₆	D_x = 1.532 Mg m⁻³
M_r = 936.88	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 3754 reflections
a = 8.8886 (1) Å	θ = 2.7–25.0°
b = 10.0973 (4) Å	µ = 0.13 mm⁻¹
c = 45.2601 (7) Å	T = 150 K
V = 4062.13 (18) Å³	Block, colourless
Z = 4	0.34 × 0.30 × 0.26 mm
F(000) = 1992

Data collection top

Kappa-CCD diffractometer	4039 independent reflections
Radiation source: fine-focus sealed X-ray tube	2872 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
φ scans, and ω scans with κ offsets	θ_max = 25.0°, θ_min = 2.7°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→10
T_min = 0.957, T_max = 0.967	k = 0→12
15464 measured reflections	l = 0→53

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0417P)² + 0.4863P] where P = (F_o² + 2F_c²)/3
4039 reflections	(Δ/σ)_max = 0.001
588 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O11	0.5958 (3)	−0.8801 (3)	0.22558 (5)	0.0351 (7)
O12	0.4231 (3)	−0.7305 (3)	0.23828 (5)	0.0354 (7)
O13	0.5827 (3)	−0.9635 (3)	0.33938 (5)	0.0318 (7)
O14	0.5408 (4)	−1.1430 (3)	0.31265 (5)	0.0346 (7)
O15	0.3758 (3)	−0.8422 (3)	0.29145 (5)	0.0331 (7)
O16	0.6939 (3)	−0.8264 (3)	0.29295 (6)	0.0292 (7)
C11	0.5006 (5)	−0.8337 (4)	0.24289 (8)	0.0263 (10)
C12	0.4687 (4)	−0.9116 (4)	0.27110 (7)	0.0243 (9)
C13	0.6154 (4)	−0.9454 (4)	0.28678 (8)	0.0242 (9)
C14	0.5790 (4)	−1.0187 (4)	0.31533 (9)	0.0278 (10)
O21	0.4988 (3)	−0.2247 (3)	0.39168 (6)	0.0349 (7)
O22	0.7428 (3)	−0.2454 (3)	0.40268 (7)	0.0515 (9)
O23	0.4792 (3)	0.2176 (3)	0.42626 (5)	0.0321 (7)
O24	0.4965 (3)	0.1409 (3)	0.47261 (5)	0.0326 (7)
O25	0.7593 (3)	0.0001 (3)	0.42496 (6)	0.0310 (7)
O26	0.4945 (4)	−0.1106 (3)	0.45634 (5)	0.0324 (7)
C21	0.6285 (5)	−0.1803 (4)	0.40184 (8)	0.0309 (11)
C22	0.6191 (4)	−0.0358 (4)	0.41198 (8)	0.0240 (9)
C23	0.4889 (4)	−0.0155 (4)	0.43324 (7)	0.0237 (9)
C24	0.4881 (5)	0.1267 (4)	0.44451 (9)	0.0269 (10)
O31	0.6253 (3)	1.3214 (3)	0.59324 (6)	0.0386 (8)
O32	0.3845 (3)	1.2560 (3)	0.59144 (6)	0.0344 (7)
O33	0.5900 (4)	0.8243 (3)	0.56373 (6)	0.0389 (8)
O34	0.5277 (3)	0.8806 (3)	0.51764 (5)	0.0310 (7)
O35	0.7228 (3)	1.1145 (3)	0.56409 (6)	0.0339 (7)
O36	0.4349 (3)	1.1203 (3)	0.53238 (5)	0.0311 (7)
C31	0.5215 (5)	1.2379 (4)	0.58800 (8)	0.0281 (10)
C32	0.5782 (4)	1.1028 (4)	0.57745 (8)	0.0240 (10)
C33	0.4727 (4)	1.0346 (4)	0.55629 (7)	0.0242 (9)
C34	0.5379 (5)	0.9020 (4)	0.54563 (9)	0.0273 (10)
O41	0.5487 (3)	1.9677 (3)	0.77983 (5)	0.0340 (7)
O42	0.4089 (3)	1.7966 (3)	0.76499 (5)	0.0331 (7)
O43	0.5247 (3)	2.0036 (3)	0.66220 (6)	0.0384 (8)
O44	0.5157 (3)	2.1935 (3)	0.68644 (5)	0.0340 (7)
O45	0.3139 (3)	1.9157 (3)	0.71667 (6)	0.0407 (8)
O46	0.6248 (3)	1.8663 (3)	0.70867 (6)	0.0331 (7)
C41	0.4656 (5)	1.9108 (4)	0.76181 (8)	0.0274 (10)
C42	0.4264 (4)	1.9820 (4)	0.73303 (8)	0.0295 (10)
C43	0.5701 (5)	1.9950 (4)	0.71461 (8)	0.0276 (10)
C44	0.5361 (5)	2.0643 (4)	0.68543 (9)	0.0284 (10)
N51	0.5490 (4)	−0.6821 (3)	0.34082 (6)	0.0275 (8)
N52	0.5285 (4)	−0.4632 (3)	0.36761 (6)	0.0271 (8)
C51	0.4036 (5)	−0.6770 (4)	0.35704 (9)	0.0339 (11)
C52	0.3862 (5)	−0.5367 (5)	0.36946 (10)	0.0486 (13)
C53	0.6757 (5)	−0.6715 (4)	0.36254 (9)	0.0374 (12)
C54	0.6482 (6)	−0.5447 (5)	0.38074 (10)	0.0457 (13)
C55	0.5565 (6)	−0.5738 (4)	0.31907 (8)	0.0417 (13)
C56	0.5650 (7)	−0.4425 (4)	0.33635 (8)	0.0522 (15)
N61	0.5080 (4)	0.3889 (3)	0.49091 (6)	0.0264 (8)
N62	0.5364 (4)	0.6254 (3)	0.50670 (6)	0.0277 (8)
C61	0.3588 (5)	0.4404 (4)	0.50135 (9)	0.0320 (11)
C62	0.3733 (5)	0.5909 (4)	0.50455 (9)	0.0318 (11)
C63	0.6192 (5)	0.3972 (4)	0.51560 (8)	0.0292 (10)
C64	0.6087 (5)	0.5372 (4)	0.52891 (8)	0.0305 (10)
C65	0.5616 (5)	0.4689 (4)	0.46545 (8)	0.0284 (10)
C66	0.6108 (5)	0.6048 (4)	0.47713 (7)	0.0298 (10)
N71	0.5791 (4)	1.5139 (3)	0.62859 (6)	0.0264 (8)
N72	0.5640 (4)	1.7194 (3)	0.65867 (6)	0.0286 (8)
C71	0.4387 (5)	1.5109 (4)	0.64636 (8)	0.0313 (10)
C72	0.4201 (5)	1.6456 (4)	0.66203 (8)	0.0329 (11)
C73	0.5768 (5)	1.6302 (4)	0.60825 (8)	0.0289 (10)
C74	0.5875 (5)	1.7565 (4)	0.62688 (8)	0.0337 (11)
C75	0.7122 (5)	1.5191 (5)	0.64856 (8)	0.0335 (11)
C76	0.6931 (5)	1.6371 (4)	0.66942 (9)	0.0352 (11)
H14	0.5480	−1.1659	0.2949	0.052*
H15	0.3093	−0.8002	0.2822	0.050*
H16	0.7869	−0.8411	0.2929	0.044*
H12	0.4172	−0.9961	0.2656	0.029*
H13	0.6783	−1.0032	0.2738	0.029*
H21	0.5112	−0.3002	0.3843	0.052*
H25	0.7835	0.0766	0.4194	0.046*
H26	0.5278	−0.0748	0.4718	0.049*
H22	0.6022	0.0213	0.3942	0.029*
H23	0.3934	−0.0300	0.4220	0.028*
H35	0.7660	1.1827	0.5705	0.051*
H36	0.4738	1.0916	0.5167	0.047*
H32	0.5890	1.0448	0.5952	0.029*
H33	0.3777	1.0148	0.5673	0.029*
H44	0.5504	2.2233	0.7024	0.051*
H45	0.2880	1.8466	0.7257	0.061*
H46	0.7102	1.8572	0.7164	0.050*
H42	0.3893	2.0729	0.7379	0.035*
H43	0.6472	2.0464	0.7259	0.033*
H51	0.5562	−0.7627	0.3310	0.033*
H51A	0.4034	−0.7426	0.3733	0.041*
H51B	0.3193	−0.6977	0.3435	0.041*
H52A	0.3076	−0.4890	0.3582	0.058*
H52B	0.3537	−0.5418	0.3904	0.058*
H53A	0.7732	−0.6659	0.3521	0.045*
H53B	0.6775	−0.7500	0.3756	0.045*
H54A	0.6196	−0.5692	0.4012	0.055*
H54B	0.7424	−0.4925	0.3817	0.055*
H55A	0.4661	−0.5748	0.3063	0.050*
H55B	0.6466	−0.5841	0.3064	0.050*
H56A	0.6675	−0.4051	0.3346	0.063*
H56B	0.4934	−0.3781	0.3277	0.063*
H61	0.4976	0.3010	0.4851	0.032*
H62	0.5469	0.7133	0.5125	0.033*
H61A	0.3322	0.4000	0.5206	0.038*
H61B	0.2792	0.4183	0.4869	0.038*
H62A	0.3279	0.6354	0.4872	0.038*
H62B	0.3198	0.6210	0.5225	0.038*
H63A	0.7221	0.3807	0.5081	0.035*
H63B	0.5960	0.3299	0.5308	0.035*
H64A	0.5482	0.5353	0.5473	0.037*
H64B	0.7105	0.5704	0.5338	0.037*
H65A	0.4798	0.4795	0.4508	0.034*
H65B	0.6473	0.4240	0.4557	0.034*
H66A	0.7216	0.6077	0.4793	0.036*
H66B	0.5800	0.6753	0.4632	0.036*
H71	0.5844	1.4369	0.6174	0.032*
H72	0.5591	1.7964	0.6699	0.034*
H71A	0.4440	1.4389	0.6612	0.038*
H71B	0.3512	1.4941	0.6334	0.038*
H72A	0.3365	1.6962	0.6530	0.039*
H72B	0.3973	1.6320	0.6832	0.039*
H73A	0.4824	1.6305	0.5966	0.035*
H73B	0.6626	1.6253	0.5944	0.035*
H74A	0.6875	1.7980	0.6243	0.040*
H74B	0.5097	1.8207	0.6206	0.040*
H75A	0.8054	1.5294	0.6368	0.040*
H75B	0.7196	1.4360	0.6601	0.040*
H76A	0.6729	1.6054	0.6897	0.042*
H76B	0.7863	1.6907	0.6697	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O11	0.0355 (18)	0.0404 (18)	0.0294 (15)	0.0056 (16)	0.0008 (14)	−0.0014 (14)
O12	0.044 (2)	0.0262 (17)	0.0358 (16)	0.0053 (16)	0.0031 (14)	0.0074 (14)
O13	0.0406 (19)	0.0307 (17)	0.0242 (14)	0.0009 (15)	−0.0006 (13)	−0.0019 (14)
O14	0.051 (2)	0.0261 (17)	0.0267 (15)	−0.0032 (16)	−0.0007 (15)	−0.0033 (13)
O15	0.0310 (17)	0.0384 (19)	0.0299 (15)	0.0096 (15)	0.0008 (13)	0.0018 (14)
O16	0.0270 (16)	0.0264 (17)	0.0343 (16)	−0.0022 (14)	0.0033 (14)	−0.0045 (13)
C11	0.028 (2)	0.027 (3)	0.024 (2)	−0.003 (2)	−0.004 (2)	−0.005 (2)
C12	0.028 (2)	0.020 (2)	0.025 (2)	0.0014 (19)	0.0022 (19)	−0.0021 (18)
C13	0.026 (2)	0.021 (2)	0.026 (2)	0.0006 (19)	−0.0015 (19)	0.0006 (19)
C14	0.025 (2)	0.027 (3)	0.031 (2)	0.008 (2)	−0.0035 (19)	−0.002 (2)
O21	0.0371 (19)	0.0274 (17)	0.0400 (17)	−0.0019 (15)	−0.0046 (14)	−0.0116 (14)
O22	0.031 (2)	0.033 (2)	0.090 (3)	0.0065 (17)	−0.0023 (17)	−0.0223 (19)
O23	0.0382 (19)	0.0248 (17)	0.0335 (15)	0.0037 (15)	−0.0001 (14)	0.0013 (14)
O24	0.0431 (18)	0.0289 (17)	0.0259 (15)	−0.0009 (15)	0.0031 (14)	−0.0027 (13)
O25	0.0287 (17)	0.0255 (18)	0.0388 (17)	−0.0034 (14)	0.0008 (13)	−0.0017 (14)
O26	0.050 (2)	0.0206 (16)	0.0259 (14)	−0.0046 (16)	0.0006 (14)	0.0006 (13)
C21	0.032 (3)	0.030 (3)	0.031 (2)	−0.001 (2)	0.009 (2)	−0.001 (2)
C22	0.027 (2)	0.021 (2)	0.024 (2)	−0.003 (2)	−0.0036 (18)	−0.0012 (18)
C23	0.027 (2)	0.021 (2)	0.023 (2)	0.000 (2)	0.0017 (18)	0.0005 (18)
C24	0.024 (2)	0.023 (2)	0.033 (2)	0.002 (2)	0.0014 (19)	−0.002 (2)
O31	0.0389 (19)	0.0259 (17)	0.0510 (19)	−0.0018 (16)	0.0053 (15)	−0.0122 (14)
O32	0.0272 (18)	0.0320 (18)	0.0440 (17)	0.0035 (15)	0.0053 (14)	−0.0042 (14)
O33	0.060 (2)	0.0263 (17)	0.0302 (16)	0.0083 (17)	−0.0037 (15)	0.0036 (14)
O34	0.0424 (19)	0.0241 (16)	0.0264 (15)	−0.0019 (15)	0.0008 (14)	−0.0022 (13)
O35	0.0251 (17)	0.0317 (19)	0.0449 (18)	−0.0033 (15)	0.0063 (14)	−0.0157 (15)
O36	0.0383 (18)	0.0281 (16)	0.0269 (14)	0.0051 (15)	−0.0007 (14)	−0.0001 (13)
C31	0.034 (3)	0.026 (3)	0.024 (2)	0.000 (2)	0.001 (2)	−0.001 (2)
C32	0.023 (2)	0.025 (2)	0.023 (2)	−0.004 (2)	0.0004 (18)	−0.0005 (18)
C33	0.027 (2)	0.022 (2)	0.024 (2)	0.004 (2)	−0.0003 (18)	0.0024 (19)
C34	0.031 (3)	0.026 (3)	0.025 (2)	−0.003 (2)	0.0042 (19)	0.001 (2)
O41	0.0342 (17)	0.0340 (17)	0.0336 (15)	−0.0033 (15)	−0.0077 (14)	−0.0025 (14)
O42	0.0363 (18)	0.0270 (18)	0.0359 (15)	−0.0037 (15)	−0.0051 (14)	0.0044 (14)
O43	0.057 (2)	0.0315 (18)	0.0269 (15)	−0.0005 (16)	−0.0013 (15)	−0.0049 (14)
O44	0.0465 (19)	0.0292 (18)	0.0264 (15)	−0.0014 (16)	−0.0060 (14)	−0.0038 (13)
O45	0.0373 (19)	0.046 (2)	0.0390 (18)	−0.0108 (16)	−0.0136 (15)	0.0138 (16)
O46	0.0340 (18)	0.0281 (17)	0.0373 (16)	0.0080 (15)	−0.0064 (14)	−0.0085 (14)
C41	0.026 (2)	0.027 (3)	0.028 (2)	0.006 (2)	0.001 (2)	0.002 (2)
C42	0.027 (2)	0.027 (2)	0.034 (2)	−0.001 (2)	−0.0071 (19)	0.003 (2)
C43	0.031 (2)	0.021 (2)	0.031 (2)	0.003 (2)	0.0013 (19)	−0.0007 (19)
C44	0.028 (2)	0.023 (3)	0.035 (2)	−0.001 (2)	0.003 (2)	−0.003 (2)
N51	0.035 (2)	0.0224 (19)	0.0250 (17)	0.0028 (17)	−0.0003 (16)	−0.0039 (15)
N52	0.026 (2)	0.0264 (19)	0.0287 (18)	0.0025 (17)	0.0001 (15)	−0.0051 (16)
C51	0.029 (3)	0.030 (3)	0.043 (3)	−0.006 (2)	0.006 (2)	−0.006 (2)
C52	0.042 (3)	0.039 (3)	0.065 (3)	−0.009 (3)	0.011 (3)	−0.017 (3)
C53	0.032 (3)	0.033 (3)	0.047 (3)	0.001 (2)	−0.011 (2)	−0.008 (2)
C54	0.052 (3)	0.035 (3)	0.050 (3)	0.004 (3)	−0.013 (2)	−0.012 (2)
C55	0.072 (4)	0.026 (3)	0.027 (2)	0.002 (3)	0.008 (2)	0.000 (2)
C56	0.098 (4)	0.025 (3)	0.034 (3)	−0.001 (3)	0.012 (3)	−0.001 (2)
N61	0.026 (2)	0.0224 (19)	0.0308 (18)	−0.0007 (17)	0.0003 (16)	−0.0054 (16)
N62	0.033 (2)	0.0199 (19)	0.0303 (19)	−0.0038 (18)	−0.0014 (16)	−0.0053 (16)
C61	0.027 (3)	0.036 (3)	0.033 (2)	−0.003 (2)	−0.0005 (19)	−0.006 (2)
C62	0.030 (3)	0.026 (3)	0.040 (3)	0.003 (2)	0.002 (2)	−0.005 (2)
C63	0.034 (2)	0.028 (3)	0.026 (2)	0.001 (2)	−0.006 (2)	−0.001 (2)
C64	0.036 (3)	0.027 (2)	0.029 (2)	0.001 (2)	−0.006 (2)	0.000 (2)
C65	0.037 (3)	0.027 (2)	0.021 (2)	−0.003 (2)	0.0025 (19)	0.0007 (19)
C66	0.036 (3)	0.027 (3)	0.027 (2)	−0.003 (2)	0.0070 (19)	−0.0018 (19)
N71	0.035 (2)	0.0204 (19)	0.0241 (17)	0.0018 (17)	−0.0001 (15)	−0.0044 (15)
N72	0.040 (2)	0.025 (2)	0.0211 (17)	−0.0011 (18)	0.0018 (16)	−0.0035 (15)
C71	0.035 (3)	0.028 (3)	0.031 (2)	−0.003 (2)	0.0031 (19)	−0.0003 (19)
C72	0.029 (3)	0.035 (3)	0.034 (2)	−0.003 (2)	0.005 (2)	−0.003 (2)
C73	0.034 (3)	0.029 (2)	0.023 (2)	−0.003 (2)	0.0006 (19)	0.004 (2)
C74	0.045 (3)	0.021 (2)	0.035 (2)	−0.002 (2)	0.007 (2)	−0.004 (2)
C75	0.034 (3)	0.035 (3)	0.031 (2)	0.010 (2)	−0.0037 (19)	−0.005 (2)
C76	0.032 (3)	0.034 (3)	0.040 (3)	0.002 (2)	−0.006 (2)	−0.004 (2)

Geometric parameters (Å, º) top

O11—C11	1.244 (5)	C51—C52	1.532 (6)
O12—C11	1.267 (5)	C51—H51A	0.99
O13—C14	1.223 (4)	C51—H51B	0.99
O14—C14	1.306 (5)	C52—H52A	0.99
O14—H14	0.84	C52—H52B	0.99
O15—C12	1.422 (4)	C53—C54	1.542 (6)
O15—H15	0.84	C53—H53A	0.99
O16—C13	1.418 (4)	C53—H53B	0.99
O16—H16	0.84	C54—H54A	0.99
C11—C12	1.526 (5)	C54—H54B	0.99
C12—C13	1.523 (5)	C55—C56	1.541 (5)
C12—H12	1.00	C55—H55A	0.99
C13—C14	1.524 (5)	C55—H55B	0.99
C13—H13	1.00	C56—H56A	0.99
O21—C21	1.320 (5)	C56—H56B	0.99
O21—H21	0.84	N61—C65	1.485 (5)
O22—C21	1.211 (5)	N61—C63	1.494 (5)
O23—C24	1.237 (4)	N61—C61	1.501 (5)
O24—C24	1.282 (4)	N61—H61	0.93
O25—C22	1.425 (4)	N62—C64	1.489 (5)
O25—H25	0.84	N62—C62	1.494 (5)
O26—C23	1.421 (4)	N62—C66	1.507 (5)
O26—H26	0.84	N62—H62	0.93
C21—C22	1.532 (6)	C61—C62	1.532 (6)
C22—C23	1.519 (5)	C61—H61A	0.99
C22—H22	1.00	C61—H61B	0.99
C23—C24	1.524 (5)	C62—H62A	0.99
C23—H23	1.00	C62—H62B	0.99
O31—C31	1.272 (5)	C63—C64	1.539 (5)
O32—C31	1.242 (5)	C63—H63A	0.99
O33—C34	1.225 (4)	C63—H63B	0.99
O34—C34	1.288 (4)	C64—H64A	0.99
O35—C32	1.426 (4)	C64—H64B	0.99
O35—H35	0.84	C65—C66	1.534 (5)
O36—C33	1.425 (4)	C65—H65A	0.99
O36—H36	0.84	C65—H65B	0.99
C31—C32	1.530 (6)	C66—H66A	0.99
C32—C33	1.507 (5)	C66—H66B	0.99
C32—H32	1.00	N71—C71	1.486 (5)
C33—C34	1.537 (5)	N71—C75	1.490 (5)
C33—H33	1.00	N71—C73	1.491 (5)
O41—C41	1.241 (4)	N71—H71	0.93
O42—C41	1.267 (5)	N72—C72	1.488 (5)
O43—C44	1.221 (4)	N72—C76	1.498 (5)
O44—C44	1.318 (4)	N72—C74	1.501 (5)
O44—H44	0.84	N72—H72	0.93
O45—C42	1.413 (4)	C71—C72	1.543 (5)
O45—H45	0.84	C71—H71A	0.99
O46—C43	1.413 (4)	C71—H71B	0.99
O46—H46	0.84	C72—H72A	0.99
C41—C42	1.528 (5)	C72—H72B	0.99
C42—C43	1.531 (5)	C73—C74	1.532 (5)
C42—H42	1.00	C73—H73A	0.99
C43—C44	1.525 (5)	C73—H73B	0.99
C43—H43	1.00	C74—H74A	0.99
N51—C55	1.473 (5)	C74—H74B	0.99
N51—C51	1.487 (5)	C75—C76	1.529 (6)
N51—C53	1.499 (5)	C75—H75A	0.99
N51—H51	0.93	C75—H75B	0.99
N52—C56	1.467 (5)	C76—H76A	0.99
N52—C52	1.469 (5)	C76—H76B	0.99
N52—C54	1.470 (5)

C14—O14—H14	109.5	C53—C54—H54A	109.4
C12—O15—H15	109.5	N52—C54—H54B	109.4
C13—O16—H16	109.5	C53—C54—H54B	109.4
O11—C11—O12	125.1 (4)	H54A—C54—H54B	108.0
O11—C11—C12	117.3 (4)	N51—C55—C56	107.6 (3)
O12—C11—C12	117.4 (3)	N51—C55—H55A	110.2
O15—C12—C13	107.8 (3)	C56—C55—H55A	110.2
O15—C12—C11	113.3 (3)	N51—C55—H55B	110.2
C13—C12—C11	110.2 (3)	C56—C55—H55B	110.2
O15—C12—H12	108.4	H55A—C55—H55B	108.5
C13—C12—H12	108.4	N52—C56—C55	110.9 (3)
C11—C12—H12	108.4	N52—C56—H56A	109.5
O16—C13—C12	108.8 (3)	C55—C56—H56A	109.5
O16—C13—C14	110.4 (3)	N52—C56—H56B	109.5
C12—C13—C14	108.8 (3)	C55—C56—H56B	109.5
O16—C13—H13	109.6	H56A—C56—H56B	108.1
C12—C13—H13	109.6	C65—N61—C63	109.7 (3)
C14—C13—H13	109.6	C65—N61—C61	109.8 (3)
O13—C14—O14	121.8 (4)	C63—N61—C61	109.2 (3)
O13—C14—C13	121.9 (4)	C65—N61—H61	109.3
O14—C14—C13	116.3 (3)	C63—N61—H61	109.3
C21—O21—H21	109.5	C61—N61—H61	109.3
C22—O25—H25	109.5	C64—N62—C62	108.9 (3)
C23—O26—H26	109.5	C64—N62—C66	109.1 (3)
O22—C21—O21	124.0 (4)	C62—N62—C66	109.6 (3)
O22—C21—C22	123.6 (4)	C64—N62—H62	109.7
O21—C21—C22	112.4 (4)	C62—N62—H62	109.7
O25—C22—C23	111.8 (3)	C66—N62—H62	109.7
O25—C22—C21	108.5 (3)	N61—C61—C62	107.4 (3)
C23—C22—C21	111.1 (3)	N61—C61—H61A	110.2
O25—C22—H22	108.5	C62—C61—H61A	110.2
C23—C22—H22	108.5	N61—C61—H61B	110.2
C21—C22—H22	108.5	C62—C61—H61B	110.2
O26—C23—C22	110.4 (3)	H61A—C61—H61B	108.5
O26—C23—C24	113.0 (3)	N62—C62—C61	108.6 (3)
C22—C23—C24	110.0 (3)	N62—C62—H62A	110.0
O26—C23—H23	107.7	C61—C62—H62A	110.0
C22—C23—H23	107.7	N62—C62—H62B	110.0
C24—C23—H23	107.7	C61—C62—H62B	110.0
O23—C24—O24	125.7 (4)	H62A—C62—H62B	108.4
O23—C24—C23	118.4 (3)	N61—C63—C64	107.7 (3)
O24—C24—C23	115.9 (3)	N61—C63—H63A	110.2
C32—O35—H35	109.5	C64—C63—H63A	110.2
C33—O36—H36	109.5	N61—C63—H63B	110.2
O32—C31—O31	126.2 (4)	C64—C63—H63B	110.2
O32—C31—C32	119.5 (4)	H63A—C63—H63B	108.5
O31—C31—C32	114.2 (4)	N62—C64—C63	108.1 (3)
O35—C32—C33	109.2 (3)	N62—C64—H64A	110.1
O35—C32—C31	110.8 (3)	C63—C64—H64A	110.1
C33—C32—C31	113.6 (3)	N62—C64—H64B	110.1
O35—C32—H32	107.6	C63—C64—H64B	110.1
C33—C32—H32	107.6	H64A—C64—H64B	108.4
C31—C32—H32	107.6	N61—C65—C66	108.1 (3)
O36—C33—C32	110.6 (3)	N61—C65—H65A	110.1
O36—C33—C34	112.3 (3)	C66—C65—H65A	110.1
C32—C33—C34	111.3 (3)	N61—C65—H65B	110.1
O36—C33—H33	107.5	C66—C65—H65B	110.1
C32—C33—H33	107.5	H65A—C65—H65B	108.4
C34—C33—H33	107.5	N62—C66—C65	107.7 (3)
O33—C34—O34	125.2 (4)	N62—C66—H66A	110.2
O33—C34—C33	119.4 (3)	C65—C66—H66A	110.2
O34—C34—C33	115.4 (4)	N62—C66—H66B	110.2
C44—O44—H44	109.5	C65—C66—H66B	110.2
C42—O45—H45	109.5	H66A—C66—H66B	108.5
C43—O46—H46	109.5	C71—N71—C75	109.8 (3)
O41—C41—O42	125.6 (3)	C71—N71—C73	109.8 (3)
O41—C41—C42	118.6 (4)	C75—N71—C73	111.0 (3)
O42—C41—C42	115.8 (4)	C71—N71—H71	108.7
O45—C42—C41	112.7 (3)	C75—N71—H71	108.7
O45—C42—C43	110.2 (3)	C73—N71—H71	108.7
C41—C42—C43	108.3 (3)	C72—N72—C76	110.3 (3)
O45—C42—H42	108.5	C72—N72—C74	110.0 (3)
C41—C42—H42	108.5	C76—N72—C74	110.1 (3)
C43—C42—H42	108.5	C72—N72—H72	108.8
O46—C43—C44	109.0 (3)	C76—N72—H72	108.8
O46—C43—C42	108.2 (3)	C74—N72—H72	108.8
C44—C43—C42	110.2 (3)	N71—C71—C72	108.7 (3)
O46—C43—H43	109.8	N71—C71—H71A	110.0
C44—C43—H43	109.8	C72—C71—H71A	110.0
C42—C43—H43	109.8	N71—C71—H71B	110.0
O43—C44—O44	121.0 (4)	C72—C71—H71B	110.0
O43—C44—C43	122.1 (4)	H71A—C71—H71B	108.3
O44—C44—C43	116.8 (3)	N72—C72—C71	107.6 (3)
C55—N51—C51	110.1 (3)	N72—C72—H72A	110.2
C55—N51—C53	110.5 (3)	C71—C72—H72A	110.2
C51—N51—C53	109.1 (3)	N72—C72—H72B	110.2
C55—N51—H51	109.0	C71—C72—H72B	110.2
C51—N51—H51	109.0	H72A—C72—H72B	108.5
C53—N51—H51	109.0	N71—C73—C74	108.3 (3)
C56—N52—C52	108.5 (3)	N71—C73—H73A	110.0
C56—N52—C54	108.1 (4)	C74—C73—H73A	110.0
C52—N52—C54	108.5 (3)	N71—C73—H73B	110.0
N51—C51—C52	107.5 (3)	C74—C73—H73B	110.0
N51—C51—H51A	110.2	H73A—C73—H73B	108.4
C52—C51—H51A	110.2	N72—C74—C73	108.1 (3)
N51—C51—H51B	110.2	N72—C74—H74A	110.1
C52—C51—H51B	110.2	C73—C74—H74A	110.1
H51A—C51—H51B	108.5	N72—C74—H74B	110.1
N52—C52—C51	111.1 (4)	C73—C74—H74B	110.1
N52—C52—H52A	109.4	H74A—C74—H74B	108.4
C51—C52—H52A	109.4	N71—C75—C76	108.3 (3)
N52—C52—H52B	109.4	N71—C75—H75A	110.0
C51—C52—H52B	109.4	C76—C75—H75A	110.0
H52A—C52—H52B	108.0	N71—C75—H75B	110.0
N51—C53—C54	106.9 (3)	C76—C75—H75B	110.0
N51—C53—H53A	110.3	H75A—C75—H75B	108.4
C54—C53—H53A	110.3	N72—C76—C75	108.5 (3)
N51—C53—H53B	110.3	N72—C76—H76A	110.0
C54—C53—H53B	110.3	C75—C76—H76A	110.0
H53A—C53—H53B	108.6	N72—C76—H76B	110.0
N52—C54—C53	111.3 (3)	C75—C76—H76B	110.0
N52—C54—H54A	109.4	H76A—C76—H76B	108.4

O11—C11—C12—O15	171.3 (3)	C42—C43—C44—O44	75.8 (5)
O12—C11—C12—O15	−12.0 (5)	C55—N51—C51—C52	−52.9 (4)
O11—C11—C12—C13	50.4 (5)	C53—N51—C51—C52	68.5 (4)
O12—C11—C12—C13	−133.0 (4)	C56—N52—C52—C51	66.1 (5)
O15—C12—C13—O16	−66.6 (4)	C54—N52—C52—C51	−51.1 (5)
C11—C12—C13—O16	57.6 (4)	N51—C51—C52—N52	−13.0 (5)
O15—C12—C13—C14	53.8 (4)	C55—N51—C53—C54	66.7 (4)
C11—C12—C13—C14	178.0 (3)	C51—N51—C53—C54	−54.5 (4)
O16—C13—C14—O13	17.5 (5)	C56—N52—C54—C53	−52.1 (5)
C12—C13—C14—O13	−101.9 (4)	C52—N52—C54—C53	65.4 (4)
O16—C13—C14—O14	−163.8 (3)	N51—C53—C54—N52	−11.2 (5)
C12—C13—C14—O14	76.9 (4)	C51—N51—C55—C56	67.6 (5)
O22—C21—C22—O25	−6.1 (5)	C53—N51—C55—C56	−53.0 (5)
O21—C21—C22—O25	174.9 (3)	C52—N52—C56—C55	−50.7 (5)
O22—C21—C22—C23	−129.4 (4)	C54—N52—C56—C55	66.7 (5)
O21—C21—C22—C23	51.6 (4)	N51—C55—C56—N52	−12.9 (6)
O25—C22—C23—O26	−70.4 (4)	C65—N61—C61—C62	−48.5 (4)
C21—C22—C23—O26	51.0 (4)	C63—N61—C61—C62	71.9 (4)
O25—C22—C23—C24	55.0 (4)	C64—N62—C62—C61	−48.3 (4)
C21—C22—C23—C24	176.4 (3)	C66—N62—C62—C61	71.0 (4)
O26—C23—C24—O23	−178.0 (3)	N61—C61—C62—N62	−19.7 (4)
C22—C23—C24—O23	58.0 (5)	C65—N61—C63—C64	71.9 (4)
O26—C23—C24—O24	1.8 (5)	C61—N61—C63—C64	−48.6 (4)
C22—C23—C24—O24	−122.1 (4)	C62—N62—C64—C63	71.8 (4)
O32—C31—C32—O35	157.4 (3)	C66—N62—C64—C63	−47.8 (4)
O31—C31—C32—O35	−24.5 (5)	N61—C63—C64—N62	−19.8 (4)
O32—C31—C32—C33	33.9 (5)	C63—N61—C65—C66	−47.8 (4)
O31—C31—C32—C33	−147.9 (3)	C61—N61—C65—C66	72.3 (4)
O35—C32—C33—O36	−71.9 (4)	C64—N62—C66—C65	72.0 (4)
C31—C32—C33—O36	52.5 (4)	C62—N62—C66—C65	−47.2 (4)
O35—C32—C33—C34	53.7 (4)	N61—C65—C66—N62	−20.4 (4)
C31—C32—C33—C34	178.0 (3)	C75—N71—C71—C72	68.0 (4)
O36—C33—C34—O33	172.4 (4)	C73—N71—C71—C72	−54.3 (4)
C32—C33—C34—O33	47.8 (5)	C76—N72—C72—C71	−53.9 (4)
O36—C33—C34—O34	−9.9 (5)	C74—N72—C72—C71	67.7 (4)
C32—C33—C34—O34	−134.5 (4)	N71—C71—C72—N72	−11.4 (4)
O41—C41—C42—O45	−171.0 (3)	C71—N71—C73—C74	67.9 (4)
O42—C41—C42—O45	9.1 (5)	C75—N71—C73—C74	−53.7 (4)
O41—C41—C42—C43	66.8 (4)	C72—N72—C74—C73	−54.3 (4)
O42—C41—C42—C43	−113.1 (4)	C76—N72—C74—C73	67.4 (4)
O45—C42—C43—O46	−63.4 (4)	N71—C73—C74—N72	−11.6 (4)
C41—C42—C43—O46	60.3 (4)	C71—N71—C75—C76	−54.6 (4)
O45—C42—C43—C44	55.7 (4)	C73—N71—C75—C76	67.0 (4)
C41—C42—C43—C44	179.4 (3)	C72—N72—C76—C75	67.4 (4)
O46—C43—C44—O43	16.1 (6)	C74—N72—C76—C75	−54.2 (4)
C42—C43—C44—O43	−102.5 (5)	N71—C75—C76—N72	−10.6 (5)
O46—C43—C44—O44	−165.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O14—H14···O12ⁱ	0.84	1.66	2.489 (3)	171
O15—H15···O42ⁱⁱ	0.84	2.09	2.837 (4)	148
O15—H15···O12	0.84	2.34	2.691 (3)	106
O16—H16···O41ⁱⁱⁱ	0.84	2.03	2.761 (4)	145
O21—H21···N52	0.84	1.82	2.656 (4)	178
O25—H25···O32^iv	0.84	1.98	2.803 (4)	168
O26—H26···O34^v	0.84	2.12	2.791 (3)	136
O26—H26···O24	0.84	2.20	2.643 (4)	113
O35—H35···O31	0.84	2.14	2.619 (4)	116
O35—H35···O23^iv	0.84	2.15	2.874 (4)	144
O36—H36···O24^vi	0.84	2.07	2.768 (3)	141
O36—H36···O34	0.84	2.18	2.643 (4)	114
O44—H44···O42^vii	0.84	1.69	2.523 (3)	170
O45—H45···O42	0.84	2.14	2.635 (4)	118
O45—H45···O12^viii	0.84	2.29	2.982 (4)	141
O46—H46···O11^ix	0.84	1.79	2.603 (4)	162
N51—H51···O13	0.93	2.08	2.858 (4)	141
N51—H51···O16	0.93	2.21	2.911 (4)	132
N61—H61···O24	0.93	1.71	2.640 (4)	174
N62—H62···O34	0.93	1.71	2.625 (4)	166
N71—H71···O31	0.93	1.64	2.551 (4)	166
N72—H72···O46	0.93	1.98	2.759 (4)	140
N72—H72···O43	0.93	2.14	2.895 (4)	137

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1/2, −y+1, z−1/2; (iii) −x+3/2, −y+1, z−1/2; (iv) x+1/2, −y+3/2, −z+1; (v) x, y−1, z; (vi) x, y+1, z; (vii) −x+1, y+1/2, −z+3/2; (viii) −x+1/2, −y+1, z+1/2; (ix) −x+3/2, −y+1, z+1/2.

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Chiral versus racemic building blocks in supra­molecular chemistry: tartrate salts of organic diamines

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Chiral versus racemic building blocks in supramolecular chemistry: tartrate salts of organic diamines