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

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

doi:10.1107/S0108768102000642

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

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

(S)-Malic acid forms a salt with N,N′-dimethylpiperazine, [MeN(CH₂CH₂)₂NMe]H₂²⁺·2C₄H₅O₅⁻ (1) (triclinic, P1, Z′ = 1), in which the cations link pairs of hydrogen-bonded anion chains to form a molecular ladder. With 4,4′-bipyridyl, (S)-malic acid forms a 1:1 adduct which crystallizes from methanol to yield two polymorphs, (2) (triclinic, P1, Z′ = 1) and (3) (monoclinic, C2, Z′ = 1), while racemic malic acid with 4,4′-bipyridyl also forms a 1:1 adduct, (4) (monoclinic, P2₁/c, Z′ = 1). In each of (2), (3) and (4) the components are linked by O—H

N and N—H

O into chains of alternating bipyridyl and malate units, which are linked into sheets by O—H

O hydrogen bonds. In each of the 1:1 adducts (5) and (6), formed by, respectively, (S)-malic acid and racemic malic acid with 1,2-bis(4′-pyridyl)ethene, the diamine is disordered over two sets of sites, related by a 180° rotation about the N

N vector. In (5), (C₁₂H₁₀N₂)H⁺·C₄H₅O₅⁻ (triclinic, P1, Z′ = 1), the components are again linked by a combination of N—H

O and O—H

O hydrogen bonds into sheets, while in (6) (triclinic, P ${\overline 1}$ , Z′ = 0.5) there is only partial transfer of the H atom from O to N and the malate component is disordered across a centre of inversion. With 1,4-diazabicyclo[2.2.2]octane, racemic malic acid forms a 1:2 salt, [(C₆H₁₂N₂)H₂]²⁺·2C₄H₅O₅⁻ (7) (monoclinic, P2₁/c, Z′ = 2), while (S)-malic acid forms a 1:1 adduct, (8) (monoclinic, P2₁, Z′ = 3). There are thus six independent molecular components in each. In (7) the ions are linked by an extensive series of N—H

O and O—H

O hydrogen bonds into a three-dimensional framework, but in (8) there is extensive disorder involving all six components, and no refinement proved to be feasible.

Keywords: hydrogen bonding; malic acid; chiral versus racemic; supramolecular chemistry.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768102000642/na0134sup1.cif Contains datablocks global, 1, 2, 3, 4, 5, 6, 7
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768102000642/na01341sup2.hkl Contains datablock 1
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768102000642/na01342sup3.hkl Contains datablock 2
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768102000642/na01343sup4.hkl Contains datablock 3
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768102000642/na01344sup5.hkl Contains datablock 4
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768102000642/na01345sup6.hkl Contains datablock 5
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768102000642/na01346sup7.hkl Contains datablock 6
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768102000642/na01347sup8.hkl Contains datablock 7

CCDC references: 188104; 188105; 188106; 188107; 188108; 188109; 188110

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).

(1) N,N'-Dimethylpiperazine–(S)-malic acid (1/2) top

Crystal data top

C₆H₁₆N₂·2(C₄H₅O₅)	Z = 1
M_r = 382.37	F(000) = 204
Triclinic, P1	D_x = 1.426 Mg m⁻³
a = 5.8757 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.8751 (4) Å	Cell parameters from 1913 reflections
c = 10.6165 (7) Å	θ = 2.8–27.6°
α = 70.345 (2)°	µ = 0.12 mm⁻¹
β = 74.500 (2)°	T = 293 K
γ = 87.435 (3)°	Plate, colourless
V = 445.24 (4) Å³	0.35 × 0.27 × 0.13 mm

Data collection top

Kappa-CCD diffractometer	2041 independent reflections
Radiation source: fine-focus sealed X-ray tube	1476 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
φ scans, and ω scans with κ offsets	θ_max = 27.6°, θ_min = 2.8°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→7
T_min = 0.959, T_max = 0.984	k = −10→10
6309 measured reflections	l = −12→13

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)] = 0.041	H-atom parameters constrained
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0602P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max < 0.001
2041 reflections	Δρ_max = 0.19 e Å⁻³
242 parameters	Δρ_min = −0.15 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: 0.106 (18)

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.

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)

0.2346 (0.0116) x + 7.8176 (0.0018) y + 2.3720 (0.0191) z = 3.9234 (0.0179)

* 0.0112 (0.0029) C11 * -0.0031 (0.0008) C12 * -0.0042 (0.0011) O11 * -0.0039 (0.0010) O12

Rms deviation of fitted atoms = 0.0065

- 0.6617 (0.0248) x + 7.0762 (0.0051) y - 1.1634 (0.0150) z = 0.3924 (0.0176)

Angle to previous plane (with approximate e.s.d.) = 19.57 (0.13)

* 0.1204 (0.0015) C11 * -0.3060 (0.0025) C12 * 0.3267 (0.0024) C13 * -0.1410 (0.0013) C14

Rms deviation of fitted atoms = 0.2423

- 2.0854 (0.0128) x + 7.0585 (0.0089) y + 0.2080 (0.0258) z = 1.8413 (0.0335)

Angle to previous plane (with approximate e.s.d.) = 18.48 (0.26)

* 0.0030 (0.0009) C13 * -0.0103 (0.0030) C14 * 0.0035 (0.0010) O13 * 0.0038 (0.0011) O14

Rms deviation of fitted atoms = 0.0059

- 1.0912 (0.0101) x + 7.2585 (0.0056) y - 0.3458 (0.0188) z = 4.1292 (0.0141)

Angle to previous plane (with approximate e.s.d.) = 11.75 (0.22)

* 0.0089 (0.0025) C21 * -0.0025 (0.0007) C22 * -0.0033 (0.0009) O21 * -0.0031 (0.0009) O22

Rms deviation of fitted atoms = 0.0051

0.4287 (0.0252) x + 7.7524 (0.0034) y + 1.9225 (0.0158) z = 6.0610 (0.0200)

Angle to previous plane (with approximate e.s.d.) = 17.20 (0.15)

* 0.1314 (0.0014) C21 * -0.3302 (0.0025) C22 * 0.3466 (0.0027) C23 * -0.1477 (0.0015) C24

Rms deviation of fitted atoms = 0.2589

0.9739 (0.0126) x + 6.8995 (0.0080) y - 1.0125 (0.0234) z = 6.4349 (0.0099)

Angle to previous plane (with approximate e.s.d.) = 18.77 (0.18)

* 0.0039 (0.0010) C23 * -0.0134 (0.0035) C24 * 0.0044 (0.0011) O23 * 0.0051 (0.0013) O24

Rms deviation of fitted atoms = 0.0077

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

	x	y	z	U_iso*/U_eq
O11	0.1017 (4)	0.2619 (4)	0.7792 (2)	0.0531 (7)
O12	−0.1490 (4)	0.2068 (4)	0.9857 (3)	0.0618 (8)
O13	−0.1483 (5)	0.1815 (4)	1.2248 (3)	0.0660 (8)
O14	0.1033 (6)	0.2531 (5)	1.3185 (3)	0.0791 (10)
O15	0.4739 (4)	0.2495 (4)	0.8703 (2)	0.0543 (7)
C11	0.0599 (6)	0.2269 (5)	0.9051 (4)	0.0406 (8)
C12	0.2603 (5)	0.1972 (5)	0.9771 (3)	0.0379 (7)
C13	0.2426 (6)	0.3012 (5)	1.0762 (3)	0.0443 (8)
C14	0.0591 (7)	0.2410 (5)	1.2163 (4)	0.0457 (9)
O21	0.9097 (4)	0.7161 (4)	0.2286 (3)	0.0514 (7)
O22	1.1659 (4)	0.7450 (3)	0.0268 (3)	0.0438 (6)
O23	1.1703 (4)	0.7377 (4)	−0.2070 (3)	0.0621 (8)
O24	0.9014 (6)	0.7595 (5)	−0.3180 (3)	0.0743 (10)
O25	0.5447 (4)	0.7033 (5)	0.1388 (3)	0.0622 (8)
C21	0.9589 (5)	0.7193 (4)	0.1065 (3)	0.0342 (7)
C22	0.7605 (5)	0.6852 (5)	0.0484 (3)	0.0388 (7)
C23	0.7780 (5)	0.8086 (5)	−0.1011 (3)	0.0427 (7)
C24	0.9540 (6)	0.7641 (5)	−0.2180 (4)	0.0464 (9)
N1	0.4785 (5)	0.6850 (4)	0.4166 (3)	0.0403 (7)
N4	0.5214 (5)	0.3149 (4)	0.5834 (3)	0.0437 (7)
C2	0.2957 (6)	0.5420 (5)	0.4492 (4)	0.0435 (8)
C3	0.4014 (7)	0.3610 (5)	0.4704 (4)	0.0460 (9)
C5	0.7014 (6)	0.4597 (5)	0.5537 (4)	0.0475 (9)
C6	0.5962 (6)	0.6408 (5)	0.5317 (4)	0.0478 (9)
C7	0.3747 (8)	0.8657 (6)	0.3894 (5)	0.0652 (12)
C8	0.6309 (8)	0.1370 (6)	0.6045 (4)	0.0646 (12)
H13	−0.1506	0.1756	1.1494	0.099*
H15	0.5841	0.2471	0.9046	0.081*
H12A	0.2615	0.0681	1.0286	0.045*
H13A	0.2145	0.4254	1.0277	0.053*
H13B	0.3963	0.3017	1.0937	0.053*
H23	1.1814	0.7548	−0.1367	0.093*
H25	0.4401	0.7193	0.0987	0.093*
H22A	0.7660	0.5600	0.0499	0.047*
H23A	0.6225	0.8088	−0.1165	0.051*
H23B	0.8169	0.9305	−0.1084	0.051*
H1	0.5897	0.6861	0.3380	0.048*
H4	0.4108	0.3089	0.6636	0.052*
H2A	0.2216	0.5694	0.3737	0.052*
H2B	0.1747	0.5388	0.5326	0.052*
H3A	0.2777	0.2695	0.4933	0.055*
H3B	0.5146	0.3618	0.3849	0.055*
H5A	0.8255	0.4637	0.4713	0.057*
H5B	0.7721	0.4319	0.6306	0.057*
H6A	0.4813	0.6405	0.6166	0.057*
H6B	0.7196	0.7325	0.5091	0.057*
H7A	0.2661	0.8711	0.4733	0.098*
H7B	0.2923	0.8848	0.3193	0.098*
H7C	0.4987	0.9576	0.3581	0.098*
H8A	0.7399	0.1372	0.5191	0.097*
H8B	0.5097	0.0434	0.6335	0.097*
H8C	0.7138	0.1154	0.6747	0.097*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O11	0.0340 (14)	0.094 (2)	0.0326 (16)	0.0004 (12)	−0.0101 (11)	−0.0210 (13)
O12	0.0277 (14)	0.120 (2)	0.0406 (16)	−0.0036 (14)	−0.0075 (11)	−0.0312 (15)
O13	0.0463 (17)	0.116 (2)	0.0355 (15)	−0.0174 (15)	−0.0021 (12)	−0.0288 (15)
O14	0.067 (2)	0.141 (3)	0.0486 (18)	0.0042 (18)	−0.0172 (15)	−0.0554 (19)
O15	0.0291 (14)	0.101 (2)	0.0328 (15)	0.0007 (13)	−0.0055 (11)	−0.0238 (13)
C11	0.0322 (19)	0.056 (2)	0.0351 (19)	0.0007 (14)	−0.0082 (15)	−0.0173 (14)
C12	0.0299 (15)	0.0521 (19)	0.0288 (16)	0.0049 (13)	−0.0050 (12)	−0.0127 (14)
C13	0.0393 (16)	0.057 (2)	0.0399 (18)	−0.0003 (14)	−0.0116 (13)	−0.0201 (15)
C14	0.045 (2)	0.062 (2)	0.036 (2)	0.0085 (16)	−0.0134 (15)	−0.0230 (16)
O21	0.0395 (15)	0.0864 (18)	0.0327 (15)	0.0006 (12)	−0.0118 (11)	−0.0237 (12)
O22	0.0289 (13)	0.0655 (15)	0.0386 (14)	0.0017 (10)	−0.0090 (10)	−0.0196 (11)
O23	0.0380 (14)	0.109 (2)	0.0451 (17)	0.0148 (15)	−0.0070 (12)	−0.0380 (16)
O24	0.063 (2)	0.129 (3)	0.0429 (18)	0.0071 (17)	−0.0163 (15)	−0.0428 (18)
O25	0.0261 (13)	0.131 (2)	0.0306 (14)	−0.0009 (14)	−0.0066 (11)	−0.0280 (14)
C21	0.0295 (17)	0.0423 (17)	0.0292 (17)	0.0032 (12)	−0.0080 (13)	−0.0103 (12)
C22	0.0289 (15)	0.0534 (19)	0.0322 (16)	−0.0018 (13)	−0.0071 (12)	−0.0126 (14)
C23	0.0330 (14)	0.063 (2)	0.0333 (16)	0.0060 (14)	−0.0112 (12)	−0.0164 (14)
C24	0.0382 (19)	0.065 (2)	0.0340 (19)	0.0025 (16)	−0.0091 (15)	−0.0149 (15)
N1	0.0300 (14)	0.0571 (17)	0.0318 (15)	−0.0021 (12)	−0.0013 (11)	−0.0174 (12)
N4	0.0424 (17)	0.0572 (18)	0.0291 (15)	0.0027 (13)	−0.0059 (12)	−0.0143 (12)
C2	0.0295 (18)	0.064 (2)	0.0348 (19)	−0.0036 (14)	−0.0056 (15)	−0.0152 (15)
C3	0.048 (2)	0.060 (2)	0.033 (2)	−0.0056 (17)	−0.0127 (16)	−0.0167 (15)
C5	0.0302 (18)	0.078 (3)	0.0326 (19)	−0.0056 (16)	−0.0090 (15)	−0.0155 (16)
C6	0.0386 (19)	0.072 (2)	0.035 (2)	−0.0124 (16)	−0.0056 (15)	−0.0235 (17)
C7	0.068 (3)	0.064 (3)	0.053 (3)	0.011 (2)	−0.002 (2)	−0.018 (2)
C8	0.071 (3)	0.070 (3)	0.042 (2)	0.017 (2)	−0.003 (2)	−0.0155 (18)

Geometric parameters (Å, º) top

O11—C11	1.227 (4)	C23—H23B	0.97
O12—C11	1.276 (4)	N1—C2	1.480 (4)
O13—C14	1.295 (5)	N1—C7	1.490 (5)
O13—H13	0.82	N1—C6	1.496 (5)
O14—C14	1.215 (5)	N1—H1	0.91
O15—C12	1.415 (4)	N4—C5	1.485 (5)
O15—H15	0.82	N4—C3	1.485 (5)
C11—C12	1.537 (5)	N4—C8	1.488 (5)
C12—C13	1.518 (4)	N4—H4	0.91
C12—H12A	0.98	C2—C3	1.499 (5)
C13—C14	1.521 (5)	C2—H2A	0.97
C13—H13A	0.97	C2—H2B	0.97
C13—H13B	0.97	C3—H3A	0.97
O21—C21	1.242 (4)	C3—H3B	0.97
O22—C21	1.262 (4)	C5—C6	1.499 (5)
O23—C24	1.308 (5)	C5—H5A	0.97
O23—H23	0.82	C5—H5B	0.97
O24—C24	1.194 (5)	C6—H6A	0.97
O25—C22	1.405 (4)	C6—H6B	0.97
O25—H25	0.82	C7—H7A	0.96
C21—C22	1.528 (5)	C7—H7B	0.96
C22—C23	1.536 (4)	C7—H7C	0.96
C22—H22A	0.98	C8—H8A	0.96
C23—C24	1.519 (4)	C8—H8B	0.96
C23—H23A	0.97	C8—H8C	0.96

C14—O13—H13	109.5	C7—N1—H1	108.0
C12—O15—H15	109.5	C6—N1—H1	108.0
O11—C11—O12	123.3 (3)	C5—N4—C3	109.9 (3)
O11—C11—C12	121.3 (3)	C5—N4—C8	110.6 (3)
O12—C11—C12	115.3 (3)	C3—N4—C8	112.1 (3)
O15—C12—C13	109.7 (3)	C5—N4—H4	108.0
O15—C12—C11	106.5 (3)	C3—N4—H4	108.0
C13—C12—C11	114.6 (2)	C8—N4—H4	108.0
O15—C12—H12A	108.6	N1—C2—C3	111.0 (3)
C13—C12—H12A	108.6	N1—C2—H2A	109.4
C11—C12—H12A	108.6	C3—C2—H2A	109.4
C12—C13—C14	119.9 (3)	N1—C2—H2B	109.4
C12—C13—H13A	107.4	C3—C2—H2B	109.4
C14—C13—H13A	107.4	H2A—C2—H2B	108.0
C12—C13—H13B	107.4	N4—C3—C2	111.3 (3)
C14—C13—H13B	107.4	N4—C3—H3A	109.4
H13A—C13—H13B	106.9	C2—C3—H3A	109.4
O14—C14—O13	120.1 (4)	N4—C3—H3B	109.4
O14—C14—C13	120.7 (4)	C2—C3—H3B	109.4
O13—C14—C13	119.1 (3)	H3A—C3—H3B	108.0
C24—O23—H23	109.5	N4—C5—C6	111.8 (3)
C22—O25—H25	109.5	N4—C5—H5A	109.2
O21—C21—O22	124.0 (3)	C6—C5—H5A	109.2
O21—C21—C22	118.9 (3)	N4—C5—H5B	109.2
O22—C21—C22	117.0 (3)	C6—C5—H5B	109.2
O25—C22—C21	107.6 (3)	H5A—C5—H5B	107.9
O25—C22—C23	110.8 (2)	N1—C6—C5	110.5 (3)
C21—C22—C23	114.3 (3)	N1—C6—H6A	109.5
O25—C22—H22A	108.0	C5—C6—H6A	109.5
C21—C22—H22A	108.0	N1—C6—H6B	109.5
C23—C22—H22A	108.0	C5—C6—H6B	109.5
C24—C23—C22	117.8 (3)	H6A—C6—H6B	108.1
C24—C23—H23A	107.9	N1—C7—H7A	109.5
C22—C23—H23A	107.9	N1—C7—H7B	109.5
C24—C23—H23B	107.9	H7A—C7—H7B	109.5
C22—C23—H23B	107.9	N1—C7—H7C	109.5
H23A—C23—H23B	107.2	H7A—C7—H7C	109.5
O24—C24—O23	121.1 (4)	H7B—C7—H7C	109.5
O24—C24—C23	122.1 (3)	N4—C8—H8A	109.5
O23—C24—C23	116.8 (3)	N4—C8—H8B	109.5
C2—N1—C7	110.8 (3)	H8A—C8—H8B	109.5
C2—N1—C6	109.4 (3)	N4—C8—H8C	109.5
C7—N1—C6	112.4 (3)	H8A—C8—H8C	109.5
C2—N1—H1	108.0	H8B—C8—H8C	109.5

O11—C11—C12—O15	10.1 (4)	C21—C22—C23—C24	78.1 (4)
O12—C11—C12—O15	−172.1 (3)	C22—C23—C24—O24	132.3 (4)
O11—C11—C12—C13	131.6 (3)	C22—C23—C24—O23	−50.4 (5)
O12—C11—C12—C13	−50.6 (4)	C7—N1—C2—C3	177.5 (3)
O15—C12—C13—C14	−166.3 (3)	C6—N1—C2—C3	−58.0 (3)
C11—C12—C13—C14	73.9 (4)	C5—N4—C3—C2	−55.6 (4)
C12—C13—C14—O14	143.7 (4)	C8—N4—C3—C2	−179.0 (3)
C12—C13—C14—O13	−38.3 (5)	N1—C2—C3—N4	58.0 (4)
O21—C21—C22—O25	15.5 (4)	C3—N4—C5—C6	55.6 (4)
O22—C21—C22—O25	−166.2 (3)	C8—N4—C5—C6	179.9 (3)
O21—C21—C22—C23	139.1 (3)	C2—N1—C6—C5	57.3 (3)
O22—C21—C22—C23	−42.6 (4)	C7—N1—C6—C5	−179.0 (3)
O25—C22—C23—C24	−160.1 (3)	N4—C5—C6—N1	−57.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···O12	0.82	1.67	2.480 (4)	169
O15—H15···O12ⁱ	0.82	1.95	2.763 (4)	172
O23—H23···O22	0.82	1.69	2.494 (4)	167
O25—H25···O22ⁱⁱ	0.82	1.94	2.751 (3)	173
N1—H1···O21	0.91	1.90	2.736 (4)	151
N1—H1···O25	0.91	2.16	2.824 (4)	129
N4—H4···O11	0.91	1.87	2.710 (4)	152
N4—H4···O15	0.91	2.21	2.849 (4)	126
C6—H6A···O23ⁱⁱⁱ	0.97	2.54	3.476 (5)	163
C7—H7A···O24ⁱⁱⁱ	0.96	2.57	3.453 (6)	153
C7—H7C···O13^iv	0.96	2.55	3.489 (6)	167
C8—H8A···O14^v	0.96	2.52	3.408 (5)	153

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

(2) 4,4'-Bipyridyl–(S)-malic acid (1/1),triclinic polymorph top

Crystal data top

C₁₀H_8.5N₂·C₄H_5.5O₅	Z = 1
M_r = 290.27	F(000) = 152
Triclinic, P1	D_x = 1.491 Mg m⁻³
a = 5.1647 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 6.2749 (5) Å	Cell parameters from 1351 reflections
c = 10.2126 (9) Å	θ = 3.7–27.4°
α = 83.235 (3)°	µ = 0.12 mm⁻¹
β = 89.808 (3)°	T = 150 K
γ = 79.601 (3)°	Block, colourless
V = 323.21 (5) Å³	0.40 × 0.30 × 0.30 mm

Data collection top

Kappa-CCD diffractometer	1465 independent reflections
Radiation source: fine-focus sealed X-ray tube	1195 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
φ scans, and ω scans with κ offsets	θ_max = 27.4°, θ_min = 3.7°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = 0→6
T_min = 0.956, T_max = 0.966	k = −7→8
3702 measured reflections	l = −13→13

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0823P)² + 0.0245P] where P = (F_o² + 2F_c²)/3
1465 reflections	(Δ/σ)_max < 0.001
195 parameters	Δρ_max = 0.41 e Å⁻³
3 restraints	Δρ_min = −0.25 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	Occ. (<1)
O1	0.4999 (4)	0.5001 (4)	0.4999 (3)	0.0299 (6)
O2	0.5276 (5)	0.1762 (4)	0.6218 (3)	0.0370 (7)
O3	0.0331 (4)	−0.0958 (4)	0.3020 (2)	0.0302 (6)
O4	0.1493 (5)	0.1301 (4)	0.1360 (2)	0.0345 (6)
O5	0.0886 (5)	0.4473 (4)	0.3617 (3)	0.0411 (7)
C1	0.4325 (7)	0.3122 (6)	0.5305 (3)	0.0251 (8)
C2	0.2265 (6)	0.2619 (5)	0.4367 (3)	0.0249 (8)
C3	0.3680 (6)	0.1000 (6)	0.3468 (3)	0.0259 (8)
C4	0.1730 (6)	0.0464 (5)	0.2506 (3)	0.0253 (8)
N11	0.8519 (6)	0.5652 (5)	0.6578 (3)	0.0257 (6)
N21	1.7390 (6)	0.7974 (5)	1.1249 (3)	0.0264 (6)
C12	0.9171 (7)	0.4272 (6)	0.7682 (4)	0.0286 (8)
C13	1.0959 (7)	0.4635 (6)	0.8609 (4)	0.0283 (8)
C14	1.2095 (6)	0.6499 (6)	0.8391 (3)	0.0228 (7)
C15	1.1430 (7)	0.7881 (6)	0.7232 (3)	0.0279 (8)
C16	0.9630 (7)	0.7417 (6)	0.6354 (3)	0.0278 (8)
C22	1.6992 (6)	0.9162 (6)	1.0073 (4)	0.0272 (8)
C23	1.5299 (7)	0.8738 (6)	0.9119 (3)	0.0266 (8)
C24	1.3973 (6)	0.6992 (6)	0.9383 (3)	0.0231 (7)
C25	1.4408 (7)	0.5763 (6)	1.0613 (4)	0.0295 (8)
C26	1.6124 (7)	0.6289 (7)	1.1515 (4)	0.0312 (9)
H1	0.6102	0.5187	0.5558	0.045*	0.50
H3	−0.0552	−0.1321	0.2421	0.045*
H5	0.1439	0.5580	0.3806	0.062*
H2	0.0974	0.1897	0.4905	0.030*
H3A	0.5062	0.1643	0.2974	0.031*
H3B	0.4538	−0.0354	0.4010	0.031*
H11	0.7372	0.5394	0.6009	0.031*	0.50
H12	0.8386	0.3010	0.7835	0.034*
H13	1.1401	0.3629	0.9380	0.034*
H15	1.2206	0.9142	0.7042	0.034*
H16	0.9174	0.8384	0.5568	0.033*
H22	1.7901	1.0346	0.9878	0.033*
H23	1.5049	0.9630	0.8294	0.032*
H25	1.3532	0.4566	1.0836	0.035*
H26	1.6413	0.5427	1.2349	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0338 (13)	0.0276 (13)	0.0302 (14)	−0.0129 (10)	−0.0120 (10)	0.0003 (10)
O2	0.0480 (16)	0.0339 (15)	0.0307 (15)	−0.0169 (13)	−0.0153 (12)	0.0054 (12)
O3	0.0375 (14)	0.0338 (15)	0.0233 (13)	−0.0186 (11)	−0.0111 (10)	−0.0007 (10)
O4	0.0467 (15)	0.0366 (15)	0.0237 (13)	−0.0199 (12)	−0.0068 (11)	0.0022 (11)
O5	0.0416 (14)	0.0304 (13)	0.0508 (17)	−0.0042 (11)	−0.0169 (12)	−0.0054 (12)
C1	0.0285 (17)	0.0284 (19)	0.0204 (18)	−0.0090 (14)	−0.0023 (13)	−0.0054 (15)
C2	0.0248 (16)	0.0241 (17)	0.0272 (19)	−0.0078 (14)	−0.0034 (13)	−0.0031 (14)
C3	0.0258 (17)	0.0280 (19)	0.0251 (18)	−0.0073 (15)	−0.0080 (13)	−0.0043 (14)
C4	0.0261 (17)	0.0230 (18)	0.028 (2)	−0.0056 (14)	−0.0046 (14)	−0.0046 (15)
N11	0.0265 (13)	0.0295 (16)	0.0232 (15)	−0.0095 (12)	−0.0049 (11)	−0.0049 (12)
N21	0.0271 (14)	0.0307 (16)	0.0231 (15)	−0.0107 (12)	−0.0048 (11)	−0.0019 (12)
C12	0.0354 (19)	0.0271 (18)	0.0258 (19)	−0.0136 (15)	−0.0076 (14)	−0.0011 (15)
C13	0.0341 (18)	0.0288 (18)	0.0233 (18)	−0.0109 (15)	−0.0092 (14)	0.0000 (14)
C14	0.0226 (15)	0.0280 (18)	0.0184 (17)	−0.0057 (14)	−0.0021 (12)	−0.0038 (13)
C15	0.0286 (16)	0.032 (2)	0.025 (2)	−0.0127 (15)	−0.0046 (14)	−0.0018 (16)
C16	0.0294 (17)	0.0305 (19)	0.0252 (19)	−0.0116 (15)	−0.0064 (13)	−0.0008 (15)
C22	0.0272 (17)	0.0301 (18)	0.026 (2)	−0.0110 (14)	−0.0045 (13)	−0.0028 (15)
C23	0.0312 (17)	0.0291 (19)	0.0210 (18)	−0.0115 (14)	−0.0034 (13)	−0.0001 (14)
C24	0.0225 (15)	0.0256 (17)	0.0228 (17)	−0.0071 (13)	−0.0039 (12)	−0.0045 (14)
C25	0.0333 (18)	0.0297 (19)	0.028 (2)	−0.0159 (16)	−0.0084 (14)	0.0032 (15)
C26	0.0341 (19)	0.039 (2)	0.023 (2)	−0.0147 (17)	−0.0073 (14)	0.0014 (16)

Geometric parameters (Å, º) top

O1—C1	1.292 (4)	N21—C26	1.341 (5)
O1—H1	0.84	C12—C13	1.391 (5)
O2—C1	1.226 (4)	C12—H12	0.95
O3—C4	1.309 (4)	C13—C14	1.395 (5)
O3—H3	0.84	C13—H13	0.95
O4—C4	1.222 (4)	C14—C15	1.387 (5)
O5—C2	1.394 (4)	C14—C24	1.501 (4)
O5—H5	0.84	C15—C16	1.385 (5)
C1—C2	1.532 (4)	C15—H15	0.95
C2—C3	1.535 (4)	C16—H16	0.95
C2—H2	1.00	C22—C23	1.391 (5)
C3—C4	1.516 (5)	C22—H22	0.95
C3—H3A	0.99	C23—C24	1.393 (5)
C3—H3B	0.99	C23—H23	0.95
N11—C16	1.333 (5)	C24—C25	1.391 (5)
N11—C12	1.342 (5)	C25—C26	1.388 (5)
N11—H11	0.88	C25—H25	0.95
N21—C22	1.333 (5)	C26—H26	0.95

C1—O1—H1	109.5	C12—C13—C14	119.0 (3)
C4—O3—H3	109.5	C12—C13—H13	120.5
C2—O5—H5	109.5	C14—C13—H13	120.5
O2—C1—O1	125.2 (3)	C15—C14—C13	118.0 (3)
O2—C1—C2	120.5 (3)	C15—C14—C24	121.1 (3)
O1—C1—C2	114.2 (3)	C13—C14—C24	120.9 (3)
O5—C2—C1	113.3 (3)	C16—C15—C14	119.8 (4)
O5—C2—C3	110.5 (3)	C16—C15—H15	120.1
C1—C2—C3	108.0 (2)	C14—C15—H15	120.1
O5—C2—H2	108.3	N11—C16—C15	121.9 (3)
C1—C2—H2	108.3	N11—C16—H16	119.0
C3—C2—H2	108.3	C15—C16—H16	119.0
C4—C3—C2	110.2 (2)	N21—C22—C23	122.7 (4)
C4—C3—H3A	109.6	N21—C22—H22	118.7
C2—C3—H3A	109.6	C23—C22—H22	118.7
C4—C3—H3B	109.6	C22—C23—C24	119.4 (3)
C2—C3—H3B	109.6	C22—C23—H23	120.3
H3A—C3—H3B	108.1	C24—C23—H23	120.3
O4—C4—O3	123.6 (3)	C25—C24—C23	117.4 (3)
O4—C4—C3	122.6 (3)	C25—C24—C14	121.4 (3)
O3—C4—C3	113.8 (3)	C23—C24—C14	121.1 (3)
C16—N11—C12	119.2 (3)	C26—C25—C24	119.9 (4)
C16—N11—H11	120.4	C26—C25—H25	120.1
C12—N11—H11	120.4	C24—C25—H25	120.1
C22—N21—C26	118.5 (3)	N21—C26—C25	122.2 (3)
N11—C12—C13	122.0 (3)	N21—C26—H26	118.9
N11—C12—H12	119.0	C25—C26—H26	118.9
C13—C12—H12	119.0

O2—C1—C2—O5	164.0 (3)	C12—N11—C16—C15	−0.4 (5)
O1—C1—C2—O5	−19.0 (4)	C14—C15—C16—N11	−0.7 (6)
O2—C1—C2—C3	−73.3 (4)	C26—N21—C22—C23	0.7 (5)
O1—C1—C2—C3	103.6 (3)	N21—C22—C23—C24	−0.7 (5)
O5—C2—C3—C4	−55.0 (3)	C22—C23—C24—C25	0.6 (5)
C1—C2—C3—C4	−179.4 (3)	C22—C23—C24—C14	179.0 (3)
C2—C3—C4—O4	100.7 (4)	C15—C14—C24—C25	172.2 (4)
C2—C3—C4—O3	−78.9 (3)	C13—C14—C24—C25	−7.6 (4)
C16—N11—C12—C13	0.5 (6)	C15—C14—C24—C23	−6.1 (5)
N11—C12—C13—C14	0.5 (6)	C13—C14—C24—C23	174.0 (4)
C12—C13—C14—C15	−1.7 (5)	C23—C24—C25—C26	−0.5 (5)
C12—C13—C14—C24	178.2 (3)	C14—C24—C25—C26	−178.9 (3)
C13—C14—C15—C16	1.8 (5)	C22—N21—C26—C25	−0.6 (6)
C24—C14—C15—C16	−178.1 (3)	C24—C25—C26—N21	0.5 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N11	0.84	1.71	2.553 (4)	175
O3—H3···N21ⁱ	0.84	1.75	2.588 (4)	176
O5—H5···O1	0.84	2.16	2.646 (3)	117
O5—H5···O3ⁱⁱ	0.84	2.20	2.823 (4)	131
N11—H11···O1	0.88	1.67	2.553 (4)	175
C13—H13···O4ⁱⁱⁱ	0.95	2.35	3.280 (5)	167
C15—H15···O2^iv	0.95	2.56	3.477 (4)	163
C23—H23···O2^iv	0.95	2.38	3.324 (4)	170
C25—H25···O4ⁱⁱⁱ	0.95	2.47	3.420 (5)	176

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

(3) 4,4'-Bipyridyl–(S)-malic acid (1/1), monoclinic polymorph top

Crystal data top

2(C₁₀H_8.5N₂)·2(C₄H_5.5O₅)	F(000) = 608
M_r = 580.54	D_x = 1.440 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 20.500 (4) Å	Cell parameters from 1263 reflections
b = 4.6656 (9) Å	θ = 2.7–25.0°
c = 14.201 (3) Å	µ = 0.11 mm⁻¹
β = 99.68 (3)°	T = 150 K
V = 1338.9 (5) Å³	Needle, colourless
Z = 2	0.25 × 0.12 × 0.12 mm

Data collection top

Kappa-CCD diffractometer	1343 independent reflections
Radiation source: fine-focus sealed X-ray tube	963 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
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 = −23→24
T_min = 0.973, T_max = 0.987	k = −5→4
4367 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)] = 0.045	H-atom parameters constrained
wR(F²) = 0.123	w = 1/[σ²(F_o²) + (0.0487P)² + 0.1485P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
1343 reflections	Δρ_max = 0.21 e Å⁻³
194 parameters	Δρ_min = −0.20 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: 0.009 (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)
O1	0.09059 (13)	0.5000 (9)	0.44330 (18)	0.0397 (9)
O2	0.20025 (13)	0.5691 (8)	0.48473 (18)	0.0344 (9)
O3	0.16031 (13)	0.8164 (9)	0.11410 (18)	0.0369 (8)
O4	0.06471 (14)	0.9767 (8)	0.14985 (19)	0.0407 (9)
O5	0.20213 (15)	0.9555 (8)	0.34347 (19)	0.0397 (9)
C1	0.1476 (2)	0.6085 (11)	0.4325 (3)	0.0302 (11)
C2	0.14279 (19)	0.8025 (11)	0.3460 (2)	0.0286 (10)
C3	0.1256 (2)	0.6267 (10)	0.2534 (3)	0.0304 (11)
C4	0.1132 (2)	0.8241 (11)	0.1667 (3)	0.0292 (10)
N11	0.09983 (17)	0.1794 (9)	0.5896 (2)	0.0325 (10)
N21	0.14390 (17)	−0.8094 (9)	0.9739 (2)	0.0333 (10)
C12	0.1568 (2)	0.0436 (11)	0.6157 (3)	0.0324 (11)
C13	0.1668 (2)	−0.1510 (12)	0.6907 (3)	0.0334 (12)
C14	0.11619 (19)	−0.2079 (11)	0.7423 (3)	0.0273 (10)
C15	0.0573 (2)	−0.0593 (12)	0.7150 (3)	0.0363 (12)
C16	0.0506 (2)	0.1280 (12)	0.6385 (3)	0.0398 (14)
C22	0.0889 (2)	−0.6581 (13)	0.9533 (3)	0.0404 (13)
C23	0.0774 (2)	−0.4598 (13)	0.8804 (3)	0.0386 (13)
C24	0.12626 (19)	−0.4156 (11)	0.8245 (3)	0.0280 (11)
C25	0.1840 (2)	−0.5704 (11)	0.8466 (3)	0.0304 (11)
C26	0.1909 (2)	−0.7639 (11)	0.9220 (3)	0.0315 (11)
H1	0.0946	0.4142	0.4960	0.060*
H3	0.1515	0.9334	0.0688	0.055*	0.50
H5	0.2233	0.9725	0.3992	0.059*
H2	0.1065	0.9441	0.3482	0.034*
H3A	0.1626	0.4949	0.2475	0.037*
H3B	0.0857	0.5097	0.2559	0.037*
H21	0.1491	−0.9361	1.0205	0.040*	0.50
H12	0.1921	0.0811	0.5819	0.039*
H13	0.2082	−0.2456	0.7068	0.040*
H15	0.0216	−0.0864	0.7490	0.044*
H16	0.0095	0.2237	0.6199	0.048*
H22	0.0553	−0.6876	0.9909	0.048*
H23	0.0370	−0.3556	0.8685	0.046*
H25	0.2188	−0.5452	0.8107	0.036*
H26	0.2311	−0.8681	0.9371	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0343 (17)	0.056 (3)	0.0283 (15)	−0.0098 (18)	0.0038 (13)	0.0139 (16)
O2	0.0278 (16)	0.044 (2)	0.0302 (15)	−0.0019 (17)	0.0014 (13)	0.0060 (15)
O3	0.0314 (16)	0.049 (2)	0.0323 (16)	0.0050 (17)	0.0122 (13)	0.0131 (16)
O4	0.0338 (17)	0.054 (2)	0.0352 (16)	0.011 (2)	0.0086 (13)	0.0153 (17)
O5	0.0422 (18)	0.045 (2)	0.0288 (14)	−0.0165 (17)	−0.0014 (13)	0.0054 (15)
C1	0.033 (2)	0.035 (3)	0.025 (2)	−0.004 (2)	0.013 (2)	−0.001 (2)
C2	0.024 (2)	0.036 (3)	0.026 (2)	−0.004 (2)	0.0047 (16)	0.002 (2)
C3	0.032 (2)	0.031 (3)	0.028 (2)	−0.003 (2)	0.0024 (18)	0.005 (2)
C4	0.030 (2)	0.032 (3)	0.024 (2)	−0.006 (3)	0.0004 (18)	0.003 (2)
N11	0.028 (2)	0.038 (3)	0.0312 (19)	−0.0003 (19)	0.0051 (16)	0.0062 (18)
N21	0.032 (2)	0.038 (3)	0.0294 (18)	−0.002 (2)	0.0036 (16)	0.0094 (18)
C12	0.033 (2)	0.036 (3)	0.031 (2)	−0.002 (2)	0.0101 (19)	0.002 (2)
C13	0.028 (2)	0.036 (3)	0.036 (2)	0.002 (2)	0.0077 (19)	0.002 (2)
C14	0.029 (2)	0.028 (3)	0.026 (2)	−0.001 (2)	0.0045 (17)	−0.001 (2)
C15	0.026 (2)	0.044 (3)	0.040 (2)	−0.003 (2)	0.0073 (19)	0.013 (2)
C16	0.027 (2)	0.050 (4)	0.042 (3)	0.003 (2)	0.003 (2)	0.015 (3)
C22	0.030 (2)	0.055 (4)	0.039 (3)	0.010 (3)	0.013 (2)	0.014 (2)
C23	0.030 (2)	0.049 (4)	0.038 (2)	0.006 (3)	0.0097 (19)	0.015 (3)
C24	0.026 (2)	0.031 (3)	0.026 (2)	−0.001 (2)	0.0021 (17)	−0.002 (2)
C25	0.024 (2)	0.037 (3)	0.030 (2)	−0.002 (2)	0.0069 (17)	0.005 (2)
C26	0.029 (2)	0.033 (3)	0.033 (2)	0.001 (2)	0.0065 (19)	0.001 (2)

Geometric parameters (Å, º) top

O1—C1	1.306 (5)	N21—H21	0.88
O1—H1	0.84	C12—C13	1.388 (7)
O2—C1	1.217 (5)	C12—H12	0.95
O3—C4	1.318 (5)	C13—C14	1.392 (5)
O3—H3	0.84	C13—H13	0.95
O4—C4	1.213 (5)	C14—C15	1.390 (6)
O5—C2	1.416 (5)	C14—C24	1.505 (6)
O5—H5	0.84	C15—C16	1.384 (6)
C1—C2	1.516 (6)	C15—H15	0.95
C2—C3	1.539 (6)	C16—H16	0.95
C2—H2	1.00	C22—C23	1.379 (7)
C3—C4	1.524 (6)	C22—H22	0.95
C3—H3A	0.99	C23—C24	1.394 (6)
C3—H3B	0.99	C23—H23	0.95
N11—C12	1.326 (5)	C24—C25	1.378 (6)
N11—C16	1.340 (5)	C25—C26	1.390 (6)
N21—C22	1.320 (6)	C25—H25	0.95
N21—C26	1.325 (5)	C26—H26	0.95

C1—O1—H1	109.5	C12—C13—C14	120.1 (4)
C4—O3—H3	109.5	C12—C13—H13	120.0
C2—O5—H5	109.5	C14—C13—H13	120.0
O2—C1—O1	126.1 (4)	C15—C14—C13	116.6 (4)
O2—C1—C2	121.0 (4)	C15—C14—C24	122.5 (4)
O1—C1—C2	112.9 (4)	C13—C14—C24	120.9 (4)
O5—C2—C1	112.5 (3)	C16—C15—C14	120.1 (4)
O5—C2—C3	108.7 (3)	C16—C15—H15	120.0
C1—C2—C3	110.4 (4)	C14—C15—H15	120.0
O5—C2—H2	108.4	N11—C16—C15	122.4 (4)
C1—C2—H2	108.4	N11—C16—H16	118.8
C3—C2—H2	108.4	C15—C16—H16	118.8
C4—C3—C2	110.5 (4)	N21—C22—C23	123.9 (4)
C4—C3—H3A	109.5	N21—C22—H22	118.0
C2—C3—H3A	109.5	C23—C22—H22	118.0
C4—C3—H3B	109.5	C22—C23—C24	118.5 (4)
C2—C3—H3B	109.5	C22—C23—H23	120.7
H3A—C3—H3B	108.1	C24—C23—H23	120.7
O4—C4—O3	124.0 (4)	C25—C24—C23	117.7 (4)
O4—C4—C3	122.3 (4)	C25—C24—C14	121.0 (4)
O3—C4—C3	113.7 (4)	C23—C24—C14	121.3 (4)
C12—N11—C16	118.4 (4)	C24—C25—C26	119.2 (4)
C22—N21—C26	117.7 (4)	C24—C25—H25	120.4
C22—N21—H21	121.2	C26—C25—H25	120.4
C26—N21—H21	121.2	N21—C26—C25	122.9 (4)
N11—C12—C13	122.5 (4)	N21—C26—H26	118.5
N11—C12—H12	118.8	C25—C26—H26	118.5
C13—C12—H12	118.8

O2—C1—C2—O5	−8.7 (6)	C12—N11—C16—C15	0.4 (7)
O1—C1—C2—O5	170.3 (4)	C14—C15—C16—N11	−1.7 (8)
O2—C1—C2—C3	112.9 (5)	C26—N21—C22—C23	1.0 (8)
O1—C1—C2—C3	−68.1 (5)	N21—C22—C23—C24	0.2 (9)
O5—C2—C3—C4	−62.5 (5)	C22—C23—C24—C25	−1.0 (7)
C1—C2—C3—C4	173.6 (3)	C22—C23—C24—C14	178.4 (4)
C2—C3—C4—O4	−70.0 (6)	C15—C14—C24—C25	176.6 (5)
C2—C3—C4—O3	108.6 (4)	C13—C14—C24—C25	−4.7 (7)
C16—N11—C12—C13	0.8 (7)	C15—C14—C24—C23	−2.8 (7)
N11—C12—C13—C14	−0.7 (7)	C13—C14—C24—C23	175.8 (5)
C12—C13—C14—C15	−0.6 (7)	C23—C24—C25—C26	0.6 (7)
C12—C13—C14—C24	−179.3 (4)	C14—C24—C25—C26	−178.8 (4)
C13—C14—C15—C16	1.7 (7)	C22—N21—C26—C25	−1.4 (7)
C24—C14—C15—C16	−179.6 (4)	C24—C25—C26—N21	0.6 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N11	0.84	1.71	2.541 (5)	169
O3—H3···N21ⁱ	0.84	1.79	2.627 (5)	173
O5—H5···O2	0.84	2.33	2.702 (4)	107
O5—H5···O2ⁱⁱ	0.84	2.12	2.932 (4)	162
N21—H21···O3ⁱⁱⁱ	0.88	1.75	2.627 (5)	179
C15—H15···O4^iv	0.95	2.48	3.403 (5)	165
C16—H16···O1^v	0.95	2.46	3.407 (6)	173

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

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

Crystal data top

C₁₀H_8.5N₂·C₄H_5.5O₅	F(000) = 608
M_r = 290.27	D_x = 1.450 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.1274 (8) Å	Cell parameters from 3105 reflections
b = 4.7459 (3) Å	θ = 2.7–27.5°
c = 20.1749 (13) Å	µ = 0.11 mm⁻¹
β = 100.565 (3)°	T = 150 K
V = 1329.74 (14) Å³	Needle, colourless
Z = 4	0.28 × 0.12 × 0.12 mm

Data collection top

Kappa-CCD diffractometer	3029 independent reflections
Radiation source: fine-focus sealed X-ray tube	1416 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.011
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→18
T_min = 0.969, T_max = 0.987	k = 0→6
11155 measured reflections	l = −26→25

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)] = 0.060	H-atom parameters constrained
wR(F²) = 0.189	w = 1/[σ²(F_o²) + (0.0815P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max < 0.001
3029 reflections	Δρ_max = 0.27 e Å⁻³
194 parameters	Δρ_min = −0.29 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: 0.008 (2)

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	0.43907 (15)	0.5037 (6)	0.08902 (10)	0.0393 (7)
O2	0.48186 (15)	0.4477 (5)	0.20084 (10)	0.0363 (6)
O3	0.11054 (15)	0.1783 (6)	0.15430 (11)	0.0410 (7)
O4	0.15342 (16)	−0.0307 (6)	0.06572 (11)	0.0438 (7)
O5	0.34279 (15)	0.0552 (6)	0.20387 (11)	0.0401 (7)
C1	0.4294 (2)	0.3980 (8)	0.14710 (15)	0.0302 (8)
C2	0.3458 (2)	0.1917 (8)	0.14221 (16)	0.0347 (9)
C3	0.2508 (2)	0.3472 (9)	0.12011 (17)	0.0401 (9)
C4	0.1666 (2)	0.1444 (8)	0.10980 (16)	0.0319 (8)
N11	0.58205 (17)	0.8388 (6)	0.09907 (12)	0.0297 (7)
N21	0.96865 (18)	1.8090 (6)	0.13977 (13)	0.0325 (7)
C12	0.6118 (2)	0.9651 (7)	0.15769 (15)	0.0309 (8)
C13	0.6874 (2)	1.1562 (8)	0.16752 (15)	0.0312 (8)
C14	0.7341 (2)	1.2177 (7)	0.11466 (14)	0.0263 (8)
C15	0.7021 (2)	1.0815 (8)	0.05357 (15)	0.0378 (9)
C16	0.6259 (2)	0.8943 (8)	0.04748 (15)	0.0390 (10)
C22	0.9463 (2)	1.6556 (8)	0.08411 (16)	0.0360 (9)
C23	0.8716 (2)	1.4607 (8)	0.07333 (16)	0.0349 (9)
C24	0.8166 (2)	1.4214 (7)	0.12356 (14)	0.0269 (8)
C25	0.8402 (2)	1.5795 (8)	0.18220 (15)	0.0316 (8)
C26	0.9163 (2)	1.7683 (7)	0.18809 (16)	0.0319 (8)
H1	0.4934	0.5801	0.0926	0.059*	0.50
H3	0.0635	0.0678	0.1455	0.062*
H5	0.3976	0.0608	0.2285	0.060*
H2	0.3524	0.0458	0.1076	0.042*
H3A	0.2424	0.4878	0.1548	0.048*
H3B	0.2523	0.4491	0.0775	0.048*
H11	0.5337	0.7191	0.0942	0.036*	0.50
H12	0.5804	0.9235	0.1943	0.037*
H13	0.7070	1.2441	0.2101	0.037*
H15	0.7325	1.1170	0.0161	0.045*
H16	0.6043	0.8032	0.0055	0.047*
H22	0.9834	1.6803	0.0497	0.043*
H23	0.8581	1.3560	0.0325	0.042*
H25	0.8048	1.5587	0.2177	0.038*
H26	0.9322	1.8744	0.2285	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0366 (13)	0.0521 (19)	0.0296 (12)	−0.0191 (12)	0.0071 (10)	0.0044 (11)
O2	0.0295 (11)	0.0476 (18)	0.0308 (12)	−0.0062 (11)	0.0027 (10)	−0.0016 (11)
O3	0.0344 (13)	0.0525 (19)	0.0383 (13)	−0.0144 (12)	0.0123 (11)	−0.0079 (12)
O4	0.0395 (14)	0.057 (2)	0.0376 (13)	−0.0102 (13)	0.0152 (11)	−0.0078 (13)
O5	0.0302 (12)	0.0501 (18)	0.0375 (13)	−0.0084 (12)	−0.0001 (10)	0.0151 (12)
C1	0.0282 (16)	0.033 (2)	0.0300 (17)	−0.0029 (16)	0.0078 (14)	0.0004 (15)
C2	0.0288 (17)	0.041 (3)	0.0337 (18)	−0.0067 (16)	0.0046 (14)	0.0063 (16)
C3	0.0314 (18)	0.048 (3)	0.0403 (19)	−0.0028 (17)	0.0050 (15)	0.0116 (17)
C4	0.0247 (16)	0.040 (2)	0.0306 (17)	0.0003 (16)	0.0036 (14)	0.0073 (16)
N11	0.0262 (13)	0.0342 (19)	0.0291 (14)	−0.0054 (13)	0.0066 (11)	−0.0020 (12)
N21	0.0293 (14)	0.0323 (19)	0.0363 (15)	−0.0040 (13)	0.0065 (12)	−0.0006 (13)
C12	0.0280 (16)	0.036 (2)	0.0311 (17)	−0.0005 (16)	0.0120 (14)	0.0005 (15)
C13	0.0274 (16)	0.039 (2)	0.0284 (17)	−0.0034 (15)	0.0099 (13)	−0.0046 (15)
C14	0.0236 (15)	0.027 (2)	0.0291 (16)	0.0002 (14)	0.0062 (13)	0.0013 (14)
C15	0.0383 (19)	0.049 (3)	0.0279 (17)	−0.0137 (18)	0.0113 (15)	0.0000 (16)
C16	0.043 (2)	0.052 (3)	0.0243 (16)	−0.0145 (19)	0.0100 (15)	−0.0034 (16)
C22	0.0319 (18)	0.045 (3)	0.0335 (18)	−0.0094 (17)	0.0133 (15)	−0.0016 (17)
C23	0.0319 (17)	0.042 (3)	0.0315 (17)	−0.0061 (16)	0.0085 (14)	−0.0031 (16)
C24	0.0254 (15)	0.027 (2)	0.0287 (16)	0.0017 (14)	0.0056 (13)	0.0044 (14)
C25	0.0294 (17)	0.037 (2)	0.0296 (17)	−0.0029 (16)	0.0080 (13)	−0.0010 (15)
C26	0.0317 (17)	0.031 (2)	0.0328 (17)	−0.0015 (16)	0.0055 (14)	−0.0023 (15)

Geometric parameters (Å, º) top

O1—C1	1.304 (4)	N21—C26	1.341 (4)
O1—H1	0.84	C12—C13	1.387 (5)
O2—C1	1.219 (4)	C12—H12	0.95
O3—C4	1.311 (4)	C13—C14	1.384 (4)
O3—H3	0.84	C13—H13	0.95
O4—C4	1.206 (4)	C14—C15	1.392 (4)
O5—C2	1.410 (4)	C14—C24	1.499 (4)
O5—H5	0.84	C15—C16	1.384 (5)
C1—C2	1.524 (5)	C15—H15	0.95
C2—C3	1.525 (5)	C16—H16	0.95
C2—H2	1.00	C22—C23	1.390 (5)
C3—C4	1.514 (5)	C22—H22	0.95
C3—H3A	0.99	C23—C24	1.398 (4)
C3—H3B	0.99	C23—H23	0.95
N11—C12	1.324 (4)	C24—C25	1.389 (4)
N11—C16	1.331 (4)	C25—C26	1.388 (4)
N11—H11	0.88	C25—H25	0.95
N21—C22	1.327 (4)	C26—H26	0.95

C1—O1—H1	109.5	C14—C13—C12	119.4 (3)
C4—O3—H3	109.5	C14—C13—H13	120.3
C2—O5—H5	109.5	C12—C13—H13	120.3
O2—C1—O1	125.3 (3)	C13—C14—C15	117.5 (3)
O2—C1—C2	121.3 (3)	C13—C14—C24	120.9 (3)
O1—C1—C2	113.4 (3)	C15—C14—C24	121.7 (3)
O5—C2—C1	112.7 (3)	C16—C15—C14	119.9 (3)
O5—C2—C3	108.2 (3)	C16—C15—H15	120.1
C1—C2—C3	109.8 (3)	C14—C15—H15	120.1
O5—C2—H2	108.7	N11—C16—C15	121.6 (3)
C1—C2—H2	108.7	N11—C16—H16	119.2
C3—C2—H2	108.7	C15—C16—H16	119.2
C4—C3—C2	111.1 (3)	N21—C22—C23	123.6 (3)
C4—C3—H3A	109.4	N21—C22—H22	118.2
C2—C3—H3A	109.4	C23—C22—H22	118.2
C4—C3—H3B	109.4	C22—C23—C24	118.8 (3)
C2—C3—H3B	109.4	C22—C23—H23	120.6
H3A—C3—H3B	108.0	C24—C23—H23	120.6
O4—C4—O3	123.9 (3)	C25—C24—C23	117.9 (3)
O4—C4—C3	123.4 (3)	C25—C24—C14	120.7 (3)
O3—C4—C3	112.7 (3)	C23—C24—C14	121.5 (3)
C12—N11—C16	119.4 (3)	C26—C25—C24	118.9 (3)
C12—N11—H11	120.3	C26—C25—H25	120.6
C16—N11—H11	120.3	C24—C25—H25	120.6
C22—N21—C26	117.3 (3)	N21—C26—C25	123.5 (3)
N11—C12—C13	122.3 (3)	N21—C26—H26	118.2
N11—C12—H12	118.9	C25—C26—H26	118.2
C13—C12—H12	118.9

O2—C1—C2—O5	−5.0 (5)	C12—N11—C16—C15	0.0 (5)
O1—C1—C2—O5	173.3 (3)	C14—C15—C16—N11	−0.4 (6)
O2—C1—C2—C3	115.7 (3)	C26—N21—C22—C23	0.9 (5)
O1—C1—C2—C3	−66.0 (4)	N21—C22—C23—C24	−0.2 (5)
O5—C2—C3—C4	−60.7 (4)	C22—C23—C24—C25	−0.4 (5)
C1—C2—C3—C4	175.8 (3)	C22—C23—C24—C14	179.1 (3)
C2—C3—C4—O4	−66.8 (4)	C13—C14—C24—C25	−8.2 (5)
C2—C3—C4—O3	112.6 (3)	C15—C14—C24—C25	172.4 (3)
C16—N11—C12—C13	0.3 (5)	C13—C14—C24—C23	172.4 (3)
N11—C12—C13—C14	−0.3 (5)	C15—C14—C24—C23	−7.0 (5)
C12—C13—C14—C15	−0.1 (5)	C23—C24—C25—C26	0.3 (5)
C12—C13—C14—C24	−179.5 (3)	C14—C24—C25—C26	−179.2 (3)
C13—C14—C15—C16	0.4 (5)	C22—N21—C26—C25	−1.0 (5)
C24—C14—C15—C16	179.8 (3)	C24—C25—C26—N21	0.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N11	0.84	1.74	2.549 (3)	161
O3—H3···N21ⁱ	0.84	1.81	2.638 (3)	171
O5—H5···O2	0.84	2.31	2.716 (3)	110
O5—H5···O2ⁱⁱ	0.84	2.08	2.889 (3)	161
N11—H11···O1	0.88	1.67	2.549 (3)	176
C12—H12···O2ⁱⁱⁱ	0.95	2.44	3.360 (4)	164
C13—H13···O5^iv	0.95	2.48	3.302 (4)	145
C16—H16···O1^v	0.95	2.39	3.327 (4)	169
C23—H23···O4^v	0.95	2.49	3.434 (4)	170

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

(5) 1,2-Bis-(4'-pyridyl)ethene–(S)-malic acid (1/1) top

Crystal data top

C₁₂H₁₁N₂·C₄H₅O₅	Z = 1
M_r = 316.31	F(000) = 166
Triclinic, P1	D_x = 1.453 Mg m⁻³
a = 4.9325 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.3343 (4) Å	Cell parameters from 1174 reflections
c = 9.3502 (7) Å	θ = 4.2–25.2°
α = 72.751 (2)°	µ = 0.11 mm⁻¹
β = 89.414 (2)°	T = 150 K
γ = 80.207 (2)°	Plate, colourless
V = 361.41 (4) Å³	0.32 × 0.30 × 0.18 mm

Data collection top

Kappa-CCD diffractometer	2167 independent reflections
Radiation source: fine-focus sealed X-ray tube	1958 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
φ scans, and ω scans with κ offsets	θ_max = 25.2°, θ_min = 4.2°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −5→5
T_min = 0.966, T_max = 0.981	k = −9→9
3171 measured reflections	l = −11→11

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0558P)² + 0.1P] where P = (F_o² + 2F_c²)/3
2167 reflections	(Δ/σ)_max = 0.004
179 parameters	Δρ_max = 0.31 e Å⁻³
65 restraints	Δρ_min = −0.27 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	Occ. (<1)
O1	0.1770 (5)	0.4736 (3)	0.7433 (3)	0.0391 (6)
O2	0.1626 (5)	0.7361 (3)	0.5892 (3)	0.0386 (6)
O3	0.8240 (6)	0.5326 (3)	0.2644 (3)	0.0493 (7)
O4	0.8080 (5)	0.2620 (3)	0.3901 (3)	0.0416 (6)
O5	0.7073 (5)	0.3826 (3)	0.6727 (3)	0.0384 (5)
C1	0.2724 (7)	0.5798 (4)	0.6424 (4)	0.0309 (7)
C2	0.5393 (7)	0.5249 (4)	0.5705 (4)	0.0316 (8)
C3	0.4595 (7)	0.4750 (5)	0.4331 (4)	0.0392 (9)
C4	0.7154 (7)	0.4256 (5)	0.3529 (4)	0.0351 (8)
N21	−1.7570 (4)	1.1735 (2)	1.2546 (2)	0.0301 (6)*	0.529 (4)
C22	−1.7068 (12)	1.2875 (6)	1.1272 (5)	0.0321 (9)*	0.529 (4)
C23	−1.4878 (10)	1.2531 (6)	1.0398 (5)	0.0289 (10)*	0.529 (4)
C24	−1.3134 (9)	1.0955 (6)	1.0842 (5)	0.0222 (9)*	0.529 (4)
C25	−1.3716 (11)	0.9785 (6)	1.2166 (5)	0.0286 (9)*	0.529 (4)
C26	−1.5886 (13)	1.0229 (5)	1.3016 (7)	0.0305 (9)*	0.529 (4)
C27	−1.0854 (10)	1.0612 (7)	0.9918 (6)	0.0285 (13)*	0.529 (4)
N11	−0.2485 (4)	0.8209 (2)	0.7372 (2)	0.0283 (6)*	0.529 (4)
C12	−0.3010 (12)	0.7007 (5)	0.8597 (5)	0.0315 (8)*	0.529 (4)
C13	−0.5164 (10)	0.7255 (6)	0.9524 (6)	0.0294 (10)*	0.529 (4)
C14	−0.6835 (10)	0.8855 (6)	0.9159 (5)	0.0242 (10)*	0.529 (4)
C15	−0.6199 (10)	1.0109 (6)	0.7908 (5)	0.0284 (10)*	0.529 (4)
C16	−0.4010 (14)	0.9770 (5)	0.7029 (8)	0.0323 (9)*	0.529 (4)
C17	−0.9085 (10)	0.9154 (7)	1.0119 (6)	0.0242 (12)*	0.529 (4)
N21A	−1.7570 (4)	1.1735 (2)	1.2546 (2)	0.0301 (6)*	0.471 (4)
C22A	−1.6700 (13)	1.2600 (7)	1.1230 (5)	0.0321 (9)*	0.471 (4)
C23A	−1.4447 (11)	1.1941 (6)	1.0542 (6)	0.0289 (10)*	0.471 (4)
C24A	−1.2970 (10)	1.0321 (6)	1.1249 (6)	0.0222 (9)*	0.471 (4)
C25A	−1.3921 (11)	0.9407 (7)	1.2601 (6)	0.0286 (9)*	0.471 (4)
C26A	−1.6298 (14)	1.0126 (5)	1.3155 (8)	0.0305 (9)*	0.471 (4)
C27A	−1.0623 (11)	0.9507 (7)	1.0616 (6)	0.0255 (14)*	0.471 (4)
N11A	−0.2485 (4)	0.8209 (2)	0.7372 (2)	0.0283 (6)*	0.471 (4)
C12A	−0.3400 (13)	0.7184 (6)	0.8596 (6)	0.0315 (8)*	0.471 (4)
C13A	−0.5672 (11)	0.7811 (7)	0.9290 (6)	0.0294 (10)*	0.471 (4)
C14A	−0.6998 (11)	0.9497 (6)	0.8719 (6)	0.0242 (10)*	0.471 (4)
C15A	−0.6001 (11)	1.0537 (7)	0.7442 (6)	0.0284 (10)*	0.471 (4)
C16A	−0.3749 (16)	0.9825 (5)	0.6789 (8)	0.0323 (9)*	0.471 (4)
C17A	−0.9387 (12)	1.0228 (8)	0.9389 (7)	0.0303 (15)*	0.471 (4)
H4	0.9464	0.2432	0.3406	0.062*
H5	0.8481	0.4130	0.6988	0.058*
H2	0.6426	0.6222	0.5382	0.038*
H3A	0.3593	0.3778	0.4653	0.047*
H3B	0.3357	0.5723	0.3635	0.047*
H22	−1.8245	1.3954	1.0954	0.039*	0.529 (4)
H23	−1.4573	1.3370	0.9499	0.035*	0.529 (4)
H25	−1.2625	0.8677	1.2491	0.034*	0.529 (4)
H26	−1.6176	0.9444	1.3951	0.037*	0.529 (4)
H27	−1.0591	1.1532	0.9072	0.034*	0.529 (4)
H11	−0.0754	0.7932	0.6629	0.034*
H12	−0.1848	0.5922	0.8849	0.038*	0.529 (4)
H13	−0.5483	0.6361	1.0378	0.035*	0.529 (4)
H15	−0.7284	1.1219	0.7648	0.034*	0.529 (4)
H16	−0.3599	1.0648	0.6186	0.039*	0.529 (4)
H17	−0.9316	0.8227	1.0966	0.029*	0.529 (4)
H22A	−1.7665	1.3716	1.0741	0.039*	0.471 (4)
H23A	−1.3922	1.2593	0.9596	0.035*	0.471 (4)
H25A	−1.2959	0.8307	1.3138	0.034*	0.471 (4)
H26A	−1.7055	0.9438	1.4011	0.037*	0.471 (4)
H27A	−0.9908	0.8347	1.1131	0.031*	0.471 (4)
H12A	−0.2503	0.6032	0.8991	0.038*	0.471 (4)
H13A	−0.6324	0.7082	1.0160	0.035*	0.471 (4)
H15A	−0.6836	1.1699	0.7028	0.034*	0.471 (4)
H16A	−0.3086	1.0512	0.5899	0.039*	0.471 (4)
H17A	−1.0163	1.1379	0.8876	0.036*	0.471 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0288 (13)	0.0401 (13)	0.0477 (14)	−0.0031 (10)	0.0083 (11)	−0.0138 (11)
O2	0.0332 (13)	0.0364 (13)	0.0435 (13)	0.0015 (10)	0.0135 (10)	−0.0125 (10)
O3	0.0509 (17)	0.0432 (15)	0.0509 (15)	0.0031 (12)	0.0160 (13)	−0.0165 (12)
O4	0.0365 (14)	0.0431 (14)	0.0511 (15)	−0.0052 (10)	0.0225 (11)	−0.0248 (11)
O5	0.0290 (12)	0.0400 (11)	0.0464 (12)	−0.0013 (8)	0.0047 (9)	−0.0159 (9)
C1	0.0288 (17)	0.0358 (18)	0.0334 (17)	−0.0079 (14)	0.0056 (14)	−0.0173 (14)
C2	0.0304 (19)	0.0326 (16)	0.0334 (16)	0.0001 (13)	0.0022 (14)	−0.0155 (13)
C3	0.0243 (18)	0.055 (2)	0.046 (2)	0.0019 (15)	0.0038 (15)	−0.0312 (17)
C4	0.0319 (19)	0.0413 (19)	0.0356 (18)	0.0016 (15)	−0.0001 (15)	−0.0212 (16)

Geometric parameters (Å, º) top

O1—C1	1.238 (4)	C12—H12	0.95
O2—C1	1.272 (4)	C13—C14	1.392 (2)
O3—C4	1.218 (4)	C13—H13	0.95
O4—C4	1.303 (4)	C14—C15	1.392 (2)
O4—H4	0.84	C14—C17	1.455 (5)
O5—C2	1.421 (4)	C15—C16	1.392 (2)
O5—H5	0.84	C15—H15	0.95
C1—C2	1.534 (4)	C16—H16	0.95
C2—C3	1.537 (4)	C17—H17	0.95
C2—H2	1.00	C22A—C23A	1.392 (2)
C3—C4	1.520 (5)	C22A—H22A	0.95
C3—H3A	0.99	C23A—C24A	1.392 (2)
C3—H3B	0.99	C23A—H23A	0.95
N21—C22	1.336 (2)	C24A—C25A	1.392 (2)
N21—C26	1.336 (2)	C24A—C27A	1.452 (5)
C22—C23	1.391 (2)	C25A—C26A	1.391 (2)
C22—H22	0.95	C25A—H25A	0.95
C23—C24	1.392 (2)	C26A—H26A	0.95
C23—H23	0.95	C27A—C17A	1.323 (6)
C24—C25	1.392 (2)	C27A—H27A	0.95
C24—C27	1.453 (5)	C12A—C13A	1.392 (2)
C25—C26	1.392 (2)	C12A—H12A	0.95
C25—H25	0.95	C13A—C14A	1.392 (2)
C26—H26	0.95	C13A—H13A	0.95
C27—C17	1.334 (5)	C14A—C15A	1.392 (2)
C27—H27	0.95	C14A—C17A	1.456 (6)
N11—C12	1.336 (2)	C15A—C16A	1.392 (2)
N11—C16	1.336 (2)	C15A—H15A	0.95
N11—H11	1.1317	C16A—H16A	0.95
C12—C13	1.391 (2)	C17A—H17A	0.95

C1—O2—H11	116.2	C13—C12—H12	118.1
C4—O4—H4	109.5	C12—C13—C14	117.8 (5)
C2—O5—H5	109.5	C12—C13—H13	121.1
O1—C1—O2	124.8 (3)	C14—C13—H13	121.1
O1—C1—C2	119.9 (3)	C13—C14—C15	117.6 (4)
O2—C1—C2	115.3 (3)	C13—C14—C17	119.0 (4)
O5—C2—C1	110.8 (3)	C15—C14—C17	123.4 (4)
O5—C2—C3	109.3 (2)	C16—C15—C14	121.4 (5)
C1—C2—C3	107.7 (2)	C16—C15—H15	119.3
O5—C2—H2	109.7	C14—C15—H15	119.3
C1—C2—H2	109.7	N11—C16—C15	119.9 (4)
C3—C2—H2	109.7	N11—C16—H16	120.0
C4—C3—C2	110.3 (2)	C15—C16—H16	120.0
C4—C3—H3A	109.6	C27—C17—C14	125.9 (4)
C2—C3—H3A	109.6	C27—C17—H17	117.0
C4—C3—H3B	109.6	C14—C17—H17	117.0
C2—C3—H3B	109.6	C23A—C22A—H22A	118.5
H3A—C3—H3B	108.1	C24A—C23A—C22A	119.5 (5)
O3—C4—O4	124.1 (3)	C24A—C23A—H23A	120.2
O3—C4—C3	121.6 (3)	C22A—C23A—H23A	120.2
O4—C4—C3	114.3 (3)	C23A—C24A—C25A	117.2 (5)
C22—N21—C26	119.2 (3)	C23A—C24A—C27A	123.9 (4)
N21—C22—C23	122.1 (4)	C25A—C24A—C27A	118.8 (4)
N21—C22—H22	118.9	C26A—C25A—C24A	119.2 (5)
C23—C22—H22	118.9	C26A—C25A—H25A	120.4
C22—C23—C24	119.9 (4)	C24A—C25A—H25A	120.4
C22—C23—H23	120.1	C25A—C26A—H26A	118.3
C24—C23—H23	120.1	C17A—C27A—C24A	126.1 (5)
C23—C24—C25	116.9 (4)	C17A—C27A—H27A	116.9
C23—C24—C27	119.3 (4)	C24A—C27A—H27A	116.9
C25—C24—C27	123.8 (4)	C13A—C12A—H12A	120.1
C26—C25—C24	120.4 (5)	C14A—C13A—C12A	120.5 (5)
C26—C25—H25	119.8	C14A—C13A—H13A	119.7
C24—C25—H25	119.8	C12A—C13A—H13A	119.7
N21—C26—C25	121.4 (4)	C13A—C14A—C15A	118.6 (5)
N21—C26—H26	119.3	C13A—C14A—C17A	123.2 (4)
C25—C26—H26	119.3	C15A—C14A—C17A	118.2 (4)
C17—C27—C24	127.5 (4)	C16A—C15A—C14A	118.1 (5)
C17—C27—H27	116.2	C16A—C15A—H15A	121.0
C24—C27—H27	116.2	C14A—C15A—H15A	121.0
C12—N11—C16	119.4 (3)	C15A—C16A—H16A	118.9
C12—N11—H11	121.1	C27A—C17A—C14A	128.8 (5)
C16—N11—H11	119.5	C27A—C17A—H17A	115.6
N11—C12—C13	123.7 (4)	C14A—C17A—H17A	115.6
N11—C12—H12	118.1

O1—C1—C2—O5	−27.5 (4)	C12—C13—C14—C17	−179.4 (5)
O2—C1—C2—O5	153.6 (3)	C13—C14—C15—C16	1.4 (10)
O1—C1—C2—C3	92.0 (3)	C17—C14—C15—C16	179.4 (7)
O2—C1—C2—C3	−86.9 (3)	C12—N11—C16—C15	−2.9 (11)
O5—C2—C3—C4	−61.7 (3)	C14—C15—C16—N11	0.7 (12)
C1—C2—C3—C4	177.9 (3)	C24—C27—C17—C14	179.4 (7)
C2—C3—C4—O3	−82.4 (4)	C13—C14—C17—C27	180.0 (5)
C2—C3—C4—O4	96.2 (3)	C15—C14—C17—C27	2.0 (8)
C26—N21—C22—C23	1.5 (8)	C22A—C23A—C24A—C25A	2.7 (9)
N21—C22—C23—C24	0.2 (8)	C22A—C23A—C24A—C27A	178.9 (6)
C22—C23—C24—C25	0.4 (8)	C23A—C24A—C25A—C26A	1.5 (10)
C22—C23—C24—C27	180.0 (5)	C27A—C24A—C25A—C26A	−174.9 (7)
C23—C24—C25—C26	−2.5 (9)	C23A—C24A—C27A—C17A	7.7 (10)
C27—C24—C25—C26	177.8 (7)	C25A—C24A—C27A—C17A	−176.2 (6)
C22—N21—C26—C25	−3.7 (11)	C12A—C13A—C14A—C15A	0.0 (9)
C24—C25—C26—N21	4.3 (12)	C12A—C13A—C14A—C17A	179.8 (6)
C23—C24—C27—C17	−175.8 (5)	C13A—C14A—C15A—C16A	0.9 (10)
C25—C24—C27—C17	3.8 (9)	C17A—C14A—C15A—C16A	−178.9 (8)
C16—N11—C12—C13	3.0 (9)	C24A—C27A—C17A—C14A	178.4 (8)
N11—C12—C13—C14	−0.9 (9)	C13A—C14A—C17A—C27A	2.5 (10)
C12—C13—C14—C15	−1.3 (8)	C15A—C14A—C17A—C27A	−177.7 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···N21ⁱ	0.84	1.76	2.591 (3)	172
O5—H5···O1ⁱⁱ	0.84	1.86	2.702 (3)	175
N11—H11···O2	1.13	1.44	2.561 (3)	171
C16—H16···O4ⁱⁱⁱ	0.95	2.51	3.451 (7)	171
C23—H23···O1^iv	0.95	2.52	3.136 (5)	123
C26—H26···O2^v	0.95	2.49	3.401 (7)	160
C27—H27···O5^iv	0.95	2.57	3.393 (6)	145

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

(6) 1,2-Bis-(4'-pyridyl)ethene–racemic malic acid (1/1) top

Crystal data top

2(C₆H₅N)·C₄H₆O₅	Z = 1
M_r = 316.31	F(000) = 166
Triclinic, P1	D_x = 1.446 Mg m⁻³
a = 4.9566 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.4178 (10) Å	Cell parameters from 1243 reflections
c = 9.2538 (14) Å	θ = 2.9–25.1°
α = 73.213 (5)°	µ = 0.11 mm⁻¹
β = 89.915 (6)°	T = 150 K
γ = 79.750 (7)°	Plate, colourless
V = 363.24 (8) Å³	0.30 × 0.30 × 0.12 mm

Data collection top

Kappa-CCD diffractometer	1286 independent reflections
Radiation source: fine-focus sealed X-ray tube	774 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.078
φ scans, and ω scans with κ offsets	θ_max = 25.1°, θ_min = 2.9°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −5→0
T_min = 0.968, T_max = 0.987	k = −10→9
3458 measured reflections	l = −10→11

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.179	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0867P)²] where P = (F_o² + 2F_c²)/3
1286 reflections	(Δ/σ)_max < 0.001
131 parameters	Δρ_max = 0.23 e Å⁻³
32 restraints	Δρ_min = −0.24 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	Occ. (<1)
O1	0.1686 (4)	0.7374 (2)	0.5969 (2)	0.0597 (7)
O2	0.1810 (4)	0.4751 (2)	0.7389 (3)	0.0821 (8)
O5	0.7175 (7)	0.3878 (4)	0.6921 (4)	0.0564 (10)	0.50
C1	0.2780 (6)	0.5790 (4)	0.6433 (4)	0.0604 (8)
C2	0.5392 (6)	0.5282 (4)	0.5671 (4)	0.0692 (9)
N11	−0.2457 (3)	0.82431 (19)	0.74047 (18)	0.0423 (6)	0.50
C12	−0.3349 (11)	0.7343 (7)	0.8692 (5)	0.0444 (10)	0.50
C13	−0.5620 (11)	0.7980 (6)	0.9377 (8)	0.0413 (14)	0.50
C14	−0.7036 (10)	0.9616 (5)	0.8708 (5)	0.0328 (13)	0.50
C15	−0.6078 (14)	1.0535 (8)	0.7368 (6)	0.0404 (14)	0.50
C16	−0.3791 (13)	0.9816 (4)	0.6747 (7)	0.0458 (10)	0.50
C17	−0.9429 (9)	1.0353 (6)	0.9373 (4)	0.0464 (10)	0.50
N21	−0.2457 (3)	0.82431 (19)	0.74047 (18)	0.0423 (6)	0.50
C22	−0.2976 (12)	0.7054 (7)	0.8627 (5)	0.0444 (10)	0.50
C23	−0.5139 (12)	0.7362 (6)	0.9528 (8)	0.0413 (14)	0.50
C24	−0.6839 (10)	0.8943 (5)	0.9170 (5)	0.0328 (13)	0.50
C25	−0.6260 (14)	1.0163 (8)	0.7892 (6)	0.0404 (14)	0.50
C26	−0.4062 (12)	0.9770 (4)	0.7040 (7)	0.0458 (10)	0.50
C27	−0.9114 (8)	0.9277 (5)	1.0110 (6)	0.0464 (10)	0.50
H1	−0.044 (6)	0.7650 (11)	0.671 (3)	0.090*
H5	0.915 (12)	0.432 (4)	0.717 (5)	0.085*	0.50
H2A	0.6349	0.6265	0.5315	0.083*
H2B	0.6549	0.4360	0.6484	0.084*	0.50
H12	−0.2396	0.6225	0.9157	0.053*	0.50
H13	−0.6198	0.7305	1.0293	0.050*	0.50
H15	−0.6988	1.1657	0.6876	0.048*	0.50
H16	−0.3162	1.0460	0.5831	0.055*	0.50
H17	−1.0213	1.1440	0.8827	0.056*	0.50
H22	−0.1837	0.5967	0.8888	0.053*	0.50
H23	−0.5458	0.6491	1.0391	0.050*	0.50
H25	−0.7362	1.1261	0.7602	0.048*	0.50
H26	−0.3691	1.0616	0.6171	0.055*	0.50
H27	−0.9292	0.8387	1.0931	0.056*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0597 (13)	0.0554 (12)	0.0605 (13)	0.0025 (9)	0.0227 (10)	−0.0197 (9)
O2	0.0610 (15)	0.0556 (13)	0.115 (2)	0.0012 (11)	0.0157 (13)	−0.0101 (13)
O5	0.053 (2)	0.047 (2)	0.060 (2)	0.0020 (17)	0.0008 (18)	−0.0091 (17)
C1	0.0547 (19)	0.0573 (18)	0.069 (2)	0.0027 (15)	0.0036 (15)	−0.0258 (15)
C2	0.0519 (18)	0.070 (2)	0.092 (2)	0.0025 (15)	0.0033 (16)	−0.0402 (17)
N11	0.0418 (13)	0.0432 (12)	0.0426 (13)	−0.0030 (9)	0.0082 (10)	−0.0164 (10)
C12	0.042 (2)	0.044 (2)	0.0486 (17)	0.0012 (16)	0.0120 (13)	−0.0213 (15)
C13	0.041 (3)	0.036 (5)	0.046 (2)	0.001 (3)	0.011 (2)	−0.015 (3)
C14	0.0357 (18)	0.025 (4)	0.032 (3)	0.003 (2)	0.003 (2)	−0.005 (3)
C15	0.0451 (19)	0.041 (3)	0.029 (4)	0.000 (2)	0.012 (3)	−0.006 (3)
C16	0.0496 (19)	0.0488 (16)	0.039 (2)	−0.0007 (13)	0.0132 (17)	−0.0189 (14)
C17	0.046 (3)	0.047 (3)	0.047 (3)	−0.005 (3)	0.004 (2)	−0.0159 (18)
N21	0.0418 (13)	0.0432 (12)	0.0426 (13)	−0.0030 (9)	0.0082 (10)	−0.0164 (10)
C22	0.042 (2)	0.044 (2)	0.0486 (17)	0.0012 (16)	0.0120 (13)	−0.0213 (15)
C23	0.041 (3)	0.036 (5)	0.046 (2)	0.001 (3)	0.011 (2)	−0.015 (3)
C24	0.0357 (18)	0.025 (4)	0.032 (3)	0.003 (2)	0.003 (2)	−0.005 (3)
C25	0.0451 (19)	0.041 (3)	0.029 (4)	0.000 (2)	0.012 (3)	−0.006 (3)
C26	0.0496 (19)	0.0488 (16)	0.039 (2)	−0.0007 (13)	0.0132 (17)	−0.0189 (14)
C27	0.046 (3)	0.047 (3)	0.047 (3)	−0.005 (3)	0.004 (2)	−0.0159 (18)

Geometric parameters (Å, º) top

O1—C1	1.292 (3)	C14—C17	1.458 (6)
O1—H1	1.2772	C15—C16	1.392 (2)
O2—C1	1.217 (4)	C15—H15	0.95
O5—C2	1.536 (5)	C16—H16	0.95
O5—H5	1.15	C17—H17	0.92
C1—C2	1.527 (4)	C22—C23	1.392 (2)
C2—C2ⁱ	1.525 (6)	C22—H22	0.95
C2—H2A	1.00	C23—C24	1.392 (2)
C2—H2B	1.001 (3)	C23—H23	0.95
N11—C12	1.336 (2)	C24—C25	1.392 (2)
N11—C16	1.336 (2)	C24—C27	1.461 (6)
C12—C13	1.392 (2)	C25—C26	1.392 (2)
C12—H12	0.95	C25—H25	0.95
C13—C14	1.392 (2)	C26—H26	0.95
C13—H13	0.95	C27—H27	0.92
C14—C15	1.392 (2)

C1—O1—H1	109.5	C13—C14—C15	117.3 (6)
C2—O5—H5	109.5	C13—C14—C17	121.9 (4)
H5—O5—H2B	110.1	C15—C14—C17	120.8 (4)
O2—C1—O1	123.4 (3)	C16—C15—C14	120.2 (6)
O2—C1—C2	121.3 (3)	C16—C15—H15	119.9
O1—C1—C2	115.2 (3)	C14—C15—H15	119.9
C1—C2—C2ⁱ	108.6 (3)	N11—C16—C15	121.7 (5)
C1—C2—O5	104.7 (3)	N11—C16—H16	119.2
C2ⁱ—C2—O5	113.9 (3)	C15—C16—H16	119.2
C1—C2—H2A	109.8	C14—C17—H17	114.4
C2ⁱ—C2—H2A	109.8	C23—C22—H22	119.1
O5—C2—H2A	109.8	C22—C23—C24	120.2 (6)
C1—C2—H2B	104.7 (3)	C22—C23—H23	119.9
C2ⁱ—C2—H2B	113.5 (3)	C24—C23—H23	119.9
H2A—C2—H2B	110.2	C25—C24—C23	117.0 (6)
C12—N11—C16	118.9 (4)	C25—C24—C27	122.5 (4)
N11—C12—C13	122.5 (5)	C23—C24—C27	120.5 (4)
N11—C12—H12	118.7	C24—C25—C26	119.8 (6)
C13—C12—H12	118.7	C24—C25—H25	120.1
C12—C13—C14	119.4 (6)	C26—C25—H25	120.1
C12—C13—H13	120.3	C25—C26—H26	118.9
C14—C13—H13	120.3	C24—C27—H27	115.1

O2—C1—C2—C2ⁱ	86.0 (4)	C13—C14—C15—C16	0.00 (9)
O1—C1—C2—C2ⁱ	−92.9 (4)	C17—C14—C15—C16	179.98 (6)
O2—C1—C2—O5	−36.0 (4)	C12—N11—C16—C15	−0.03 (7)
O1—C1—C2—O5	145.1 (3)	C14—C15—C16—N11	0.03 (10)
C16—N11—C12—C13	0.02 (3)	C22—C23—C24—C25	−0.01 (7)
N11—C12—C13—C14	0.01 (3)	C22—C23—C24—C27	180.00 (4)
C12—C13—C14—C15	−0.01 (7)	C23—C24—C25—C26	0.00 (9)
C12—C13—C14—C17	180.00 (4)	C27—C24—C25—C26	179.98 (6)

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···N11	1.28	1.29	2.556 (2)	168
O5—H5···O2ⁱⁱ	1.15	1.46	2.606 (4)	173
C16—H16···O1ⁱⁱⁱ	0.95	2.31	3.231 (6)	162
C17—H17···O5^iv	0.92	2.44	3.336 (6)	163

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

(7) 1,4-Diazabicyclo[2.2.2]octane–racemic malic acid (1/2) top

Crystal data top

C₆H₁₄N₂·2(C₄H₅O₅)	F(000) = 1616
M_r = 380.35	D_x = 1.520 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.7309 (3) Å	Cell parameters from 7524 reflections
b = 20.9103 (5) Å	θ = 2.6–27.5°
c = 12.5400 (3) Å	µ = 0.13 mm⁻¹
β = 95.1780 (13)°	T = 150 K
V = 3324.61 (14) Å³	Block, colourless
Z = 8	0.32 × 0.28 × 0.25 mm

Data collection top

Kappa-CCD diffractometer	7603 independent reflections
Radiation source: fine-focus sealed X-ray tube	4395 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
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 = −16→16
T_min = 0.960, T_max = 0.968	k = −27→0
27049 measured reflections	l = 0→16

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.168	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0827P)²] where P = (F_o² + 2F_c²)/3
7603 reflections	(Δ/σ)_max < 0.001
477 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.41 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
O31	−0.19566 (12)	0.08235 (7)	0.95529 (14)	0.0298 (4)
O32	−0.34918 (11)	0.08840 (7)	1.02664 (13)	0.0261 (4)
O33	−0.34121 (14)	0.02652 (7)	0.75445 (14)	0.0366 (4)
O34	−0.38660 (13)	−0.07572 (7)	0.72874 (14)	0.0316 (4)
O35	−0.19734 (11)	−0.04261 (7)	0.94739 (13)	0.0255 (4)
C31	−0.27671 (16)	0.05708 (10)	0.98577 (18)	0.0226 (5)
C32	−0.29190 (16)	−0.01511 (10)	0.97878 (18)	0.0217 (5)
C33	−0.38806 (17)	−0.03469 (10)	0.90436 (19)	0.0252 (5)
C34	−0.36908 (16)	−0.02398 (11)	0.78921 (19)	0.0241 (5)
O41	0.72979 (12)	0.33317 (7)	0.06519 (14)	0.0314 (4)
O42	0.87632 (12)	0.33440 (7)	−0.01937 (13)	0.0265 (4)
O43	0.89313 (15)	0.27364 (8)	0.25743 (15)	0.0398 (5)
O44	0.89804 (14)	0.16783 (7)	0.27401 (14)	0.0344 (4)
O45	0.71985 (11)	0.20890 (7)	0.07055 (14)	0.0275 (4)
C41	0.80484 (17)	0.30533 (10)	0.02710 (18)	0.0225 (5)
C42	0.81313 (16)	0.23303 (9)	0.03164 (19)	0.0214 (5)
C43	0.91113 (16)	0.20987 (10)	0.10115 (19)	0.0251 (5)
C44	0.90077 (16)	0.22107 (10)	0.21825 (19)	0.0242 (5)
O51	0.22332 (12)	0.08133 (7)	0.57270 (13)	0.0295 (4)
O52	0.36071 (11)	0.07624 (7)	0.47544 (13)	0.0249 (4)
O53	0.36421 (16)	0.01013 (8)	0.74928 (15)	0.0465 (5)
O54	0.36728 (14)	−0.09545 (7)	0.76492 (14)	0.0331 (4)
O55	0.18690 (11)	−0.04218 (7)	0.55724 (13)	0.0260 (4)
C51	0.28875 (16)	0.05042 (10)	0.52499 (18)	0.0213 (5)
C52	0.28488 (16)	−0.02247 (10)	0.52250 (18)	0.0216 (5)
C53	0.37806 (17)	−0.05265 (10)	0.59126 (19)	0.0251 (5)
C54	0.36995 (16)	−0.04155 (10)	0.70902 (19)	0.0243 (5)
O61	0.32047 (12)	0.32925 (7)	0.45456 (14)	0.0299 (4)
O62	0.16959 (12)	0.32980 (7)	0.53256 (13)	0.0248 (4)
O63	0.18862 (15)	0.26389 (7)	0.26083 (14)	0.0362 (4)
O64	0.14163 (14)	0.16205 (7)	0.23741 (14)	0.0344 (4)
O65	0.33439 (11)	0.20396 (7)	0.45648 (13)	0.0240 (4)
C61	0.24380 (16)	0.30124 (10)	0.49017 (17)	0.0207 (5)
C62	0.23717 (16)	0.22826 (9)	0.48722 (18)	0.0204 (5)
C63	0.14380 (16)	0.20343 (10)	0.41326 (18)	0.0238 (5)
C64	0.16017 (16)	0.21353 (10)	0.29713 (19)	0.0226 (5)
N11	−0.05889 (13)	0.04254 (8)	0.82428 (15)	0.0235 (4)
N12	0.08793 (14)	0.04396 (8)	0.70412 (16)	0.0237 (4)
C11	0.0026 (2)	−0.01766 (10)	0.8382 (2)	0.0356 (6)
C12	0.0948 (2)	−0.01470 (12)	0.7702 (3)	0.0529 (9)
C13	−0.10353 (18)	0.04907 (15)	0.7111 (2)	0.0418 (7)
C14	−0.0135 (2)	0.04582 (18)	0.6389 (2)	0.0654 (10)
C15	0.01182 (18)	0.09788 (10)	0.8529 (2)	0.0310 (6)
C16	0.0974 (2)	0.09986 (14)	0.7765 (3)	0.0588 (10)
N21	0.44278 (14)	0.28942 (8)	0.30983 (16)	0.0242 (4)
N22	0.58228 (13)	0.29243 (8)	0.18237 (15)	0.0231 (4)
C21	0.4336 (2)	0.23159 (12)	0.2413 (2)	0.0383 (7)
C22	0.5134 (2)	0.23524 (10)	0.1594 (2)	0.0335 (6)
C23	0.54843 (18)	0.29019 (13)	0.3709 (2)	0.0379 (6)
C24	0.63326 (18)	0.28926 (15)	0.2931 (2)	0.0422 (7)
C25	0.4282 (2)	0.34721 (12)	0.2421 (2)	0.0420 (7)
C26	0.51628 (18)	0.35108 (10)	0.1681 (2)	0.0327 (6)
H34	−0.3729	−0.0676	0.6659	0.047*
H35	−0.2009	−0.0826	0.9518	0.038*
H32	−0.3024	−0.0311	1.0522	0.026*
H33A	−0.4037	−0.0804	0.9156	0.030*
H33B	−0.4500	−0.0094	0.9218	0.030*
H44	0.8892	0.1767	0.3379	0.052*
H45	0.7121	0.1703	0.0529	0.041*
H42	0.8172	0.2167	−0.0428	0.026*
H43A	0.9214	0.1636	0.0887	0.030*
H43B	0.9740	0.2328	0.0800	0.030*
H54	0.3637	−0.0867	0.8299	0.050*
H55	0.1778	−0.0813	0.5442	0.039*
H52	0.2879	−0.0368	0.4468	0.026*
H53A	0.3796	−0.0992	0.5772	0.030*
H53B	0.4449	−0.0341	0.5707	0.030*
H64	0.1487	0.1710	0.1732	0.052*
H65	0.3342	0.1639	0.4605	0.036*
H62	0.2285	0.2129	0.5614	0.025*
H63A	0.1342	0.1572	0.4265	0.029*
H63B	0.0788	0.2258	0.4300	0.029*
H11	−0.1135	0.0420	0.8688	0.028*
H12	0.1426	0.0445	0.6597	0.028*
H11A	−0.0430	−0.0546	0.8163	0.043*
H11B	0.0286	−0.0232	0.9145	0.043*
H12A	0.1618	−0.0148	0.8169	0.064*
H12B	0.0941	−0.0528	0.7232	0.064*
H13A	−0.1410	0.0904	0.7009	0.050*
H13B	−0.1546	0.0142	0.6927	0.050*
H14A	−0.0212	0.0071	0.5935	0.079*
H14B	−0.0160	0.0837	0.5913	0.079*
H15A	0.0439	0.0933	0.9275	0.037*
H15B	−0.0292	0.1381	0.8478	0.037*
H16A	0.0910	0.1397	0.7339	0.071*
H16B	0.1675	0.0996	0.8177	0.071*
H21	0.3910	0.2883	0.3576	0.029*
H22	0.6340	0.2934	0.1345	0.028*
H21A	0.3615	0.2288	0.2046	0.046*
H21B	0.4464	0.1929	0.2859	0.046*
H22A	0.5569	0.1959	0.1626	0.040*
H22B	0.4766	0.2387	0.0866	0.040*
H23A	0.5562	0.2524	0.4185	0.045*
H23B	0.5559	0.3291	0.4159	0.045*
H24A	0.6812	0.3262	0.3069	0.051*
H24B	0.6754	0.2496	0.3028	0.051*
H25A	0.4293	0.3858	0.2879	0.050*
H25B	0.3591	0.3453	0.1992	0.050*
H26A	0.4860	0.3545	0.0928	0.039*
H26B	0.5601	0.3895	0.1855	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O31	0.0305 (9)	0.0229 (8)	0.0376 (11)	−0.0061 (7)	0.0127 (7)	−0.0043 (7)
O32	0.0283 (8)	0.0245 (8)	0.0264 (10)	0.0043 (7)	0.0080 (7)	0.0000 (7)
O33	0.0533 (11)	0.0291 (9)	0.0273 (11)	−0.0086 (8)	0.0032 (8)	0.0045 (8)
O34	0.0433 (10)	0.0309 (9)	0.0216 (10)	−0.0055 (7)	0.0086 (8)	−0.0014 (7)
O35	0.0238 (8)	0.0195 (8)	0.0341 (11)	0.0020 (6)	0.0084 (7)	0.0021 (7)
C31	0.0256 (11)	0.0249 (11)	0.0174 (13)	−0.0005 (9)	0.0027 (9)	−0.0004 (9)
C32	0.0235 (11)	0.0233 (11)	0.0188 (13)	0.0015 (9)	0.0046 (9)	0.0006 (9)
C33	0.0255 (11)	0.0264 (12)	0.0240 (14)	−0.0034 (9)	0.0029 (9)	0.0004 (10)
C34	0.0199 (11)	0.0274 (12)	0.0250 (14)	−0.0001 (9)	0.0009 (9)	0.0002 (10)
O41	0.0339 (9)	0.0236 (8)	0.0395 (11)	0.0075 (7)	0.0180 (8)	0.0065 (7)
O42	0.0291 (8)	0.0253 (8)	0.0263 (10)	−0.0008 (7)	0.0091 (7)	0.0019 (7)
O43	0.0608 (12)	0.0301 (9)	0.0280 (11)	−0.0020 (8)	0.0018 (9)	−0.0039 (8)
O44	0.0515 (11)	0.0281 (9)	0.0253 (10)	0.0041 (8)	0.0137 (9)	0.0024 (7)
O45	0.0240 (8)	0.0235 (8)	0.0362 (11)	−0.0027 (6)	0.0091 (7)	−0.0039 (7)
C41	0.0258 (11)	0.0233 (11)	0.0185 (13)	0.0012 (9)	0.0028 (9)	0.0021 (9)
C42	0.0227 (11)	0.0195 (11)	0.0224 (13)	0.0016 (8)	0.0040 (9)	−0.0030 (9)
C43	0.0237 (11)	0.0269 (12)	0.0254 (14)	0.0036 (9)	0.0057 (9)	0.0006 (10)
C44	0.0197 (10)	0.0255 (12)	0.0270 (14)	0.0004 (9)	0.0006 (9)	0.0005 (10)
O51	0.0359 (9)	0.0213 (8)	0.0336 (11)	0.0048 (7)	0.0158 (8)	0.0017 (7)
O52	0.0277 (8)	0.0241 (8)	0.0238 (9)	−0.0017 (6)	0.0082 (7)	−0.0005 (7)
O53	0.0883 (15)	0.0233 (9)	0.0267 (11)	0.0016 (9)	−0.0004 (10)	−0.0018 (8)
O54	0.0488 (10)	0.0251 (8)	0.0271 (10)	0.0058 (7)	0.0131 (8)	0.0042 (7)
O55	0.0243 (8)	0.0238 (8)	0.0306 (10)	−0.0017 (6)	0.0070 (7)	−0.0039 (7)
C51	0.0220 (10)	0.0243 (11)	0.0176 (12)	0.0001 (9)	0.0010 (9)	0.0013 (9)
C52	0.0215 (11)	0.0249 (11)	0.0188 (13)	−0.0001 (9)	0.0042 (9)	0.0000 (9)
C53	0.0251 (11)	0.0237 (11)	0.0268 (14)	0.0037 (9)	0.0035 (9)	0.0016 (10)
C54	0.0225 (11)	0.0263 (12)	0.0235 (13)	0.0028 (9)	−0.0007 (9)	0.0044 (10)
O61	0.0338 (9)	0.0233 (8)	0.0347 (11)	−0.0064 (7)	0.0141 (7)	−0.0042 (7)
O62	0.0280 (8)	0.0233 (8)	0.0239 (9)	0.0035 (6)	0.0069 (7)	0.0018 (7)
O63	0.0583 (12)	0.0257 (9)	0.0247 (10)	−0.0031 (8)	0.0043 (8)	0.0022 (7)
O64	0.0482 (10)	0.0314 (9)	0.0252 (10)	−0.0143 (8)	0.0114 (8)	−0.0086 (8)
O65	0.0246 (8)	0.0194 (8)	0.0286 (10)	0.0018 (6)	0.0054 (6)	0.0005 (7)
C61	0.0236 (11)	0.0232 (11)	0.0153 (12)	0.0012 (9)	0.0013 (9)	0.0006 (9)
C62	0.0235 (11)	0.0217 (11)	0.0168 (12)	0.0011 (9)	0.0055 (9)	0.0009 (9)
C63	0.0247 (11)	0.0259 (11)	0.0214 (13)	−0.0044 (9)	0.0051 (9)	−0.0030 (9)
C64	0.0187 (10)	0.0237 (11)	0.0253 (14)	0.0008 (9)	0.0013 (9)	−0.0012 (10)
N11	0.0200 (9)	0.0272 (10)	0.0242 (12)	−0.0009 (7)	0.0064 (8)	−0.0002 (8)
N12	0.0227 (9)	0.0247 (10)	0.0245 (11)	0.0020 (7)	0.0064 (8)	0.0026 (8)
C11	0.0454 (15)	0.0213 (12)	0.0433 (18)	0.0039 (11)	0.0210 (12)	0.0041 (11)
C12	0.0617 (18)	0.0373 (15)	0.066 (2)	0.0214 (14)	0.0401 (17)	0.0241 (15)
C13	0.0246 (12)	0.075 (2)	0.0255 (16)	0.0033 (12)	−0.0009 (11)	−0.0055 (14)
C14	0.0256 (14)	0.141 (3)	0.0294 (18)	0.0136 (17)	0.0007 (12)	0.0091 (19)
C15	0.0332 (13)	0.0261 (12)	0.0344 (16)	−0.0038 (10)	0.0073 (11)	−0.0057 (11)
C16	0.0609 (19)	0.0481 (17)	0.074 (2)	−0.0297 (15)	0.0402 (17)	−0.0342 (16)
N21	0.0218 (9)	0.0263 (10)	0.0254 (12)	−0.0015 (8)	0.0069 (8)	−0.0018 (8)
N22	0.0209 (9)	0.0251 (10)	0.0240 (11)	0.0026 (8)	0.0059 (8)	0.0022 (8)
C21	0.0414 (14)	0.0389 (14)	0.0371 (17)	−0.0138 (12)	0.0183 (12)	−0.0130 (12)
C22	0.0391 (14)	0.0252 (12)	0.0384 (17)	−0.0041 (10)	0.0160 (12)	−0.0061 (11)
C23	0.0291 (13)	0.0619 (18)	0.0224 (15)	−0.0049 (12)	0.0005 (10)	−0.0039 (12)
C24	0.0237 (12)	0.078 (2)	0.0241 (15)	−0.0014 (12)	0.0011 (10)	0.0087 (14)
C25	0.0411 (15)	0.0338 (14)	0.054 (2)	0.0135 (12)	0.0207 (13)	0.0162 (13)
C26	0.0315 (12)	0.0220 (11)	0.0459 (17)	0.0030 (10)	0.0103 (11)	0.0088 (11)

Geometric parameters (Å, º) top

O31—C31	1.249 (2)	C63—C64	1.504 (3)
O32—C31	1.276 (2)	C63—H63A	0.99
O33—C34	1.208 (3)	C63—H63B	0.99
O34—C34	1.328 (3)	N11—C11	1.484 (3)
O34—H34	0.84	N11—C13	1.487 (3)
O35—C32	1.421 (2)	N11—C15	1.490 (3)
O35—H35	0.84	N11—H11	0.93
C31—C32	1.523 (3)	N12—C14	1.465 (3)
C32—C33	1.527 (3)	N12—C12	1.478 (3)
C32—H32	1.00	N12—C16	1.478 (3)
C33—C34	1.502 (3)	N12—H12	0.93
C33—H33A	0.99	C11—C12	1.514 (3)
C33—H33B	0.99	C11—H11A	0.99
O41—C41	1.250 (3)	C11—H11B	0.99
O42—C41	1.278 (2)	C12—H12A	0.99
O43—C44	1.212 (3)	C12—H12B	0.99
O44—C44	1.317 (3)	C13—C14	1.525 (3)
O44—H44	0.84	C13—H13A	0.99
O45—C42	1.417 (2)	C13—H13B	0.99
O45—H45	0.84	C14—H14A	0.99
C41—C42	1.516 (3)	C14—H14B	0.99
C42—C43	1.534 (3)	C15—C16	1.515 (3)
C42—H42	1.00	C15—H15A	0.99
C43—C44	1.505 (3)	C15—H15B	0.99
C43—H43A	0.99	C16—H16A	0.99
C43—H43B	0.99	C16—H16B	0.99
O51—C51	1.249 (2)	N21—C25	1.479 (3)
O52—C51	1.273 (2)	N21—C21	1.482 (3)
O53—C54	1.198 (3)	N21—C23	1.486 (3)
O54—C54	1.329 (3)	N21—H21	0.93
O54—H54	0.84	N22—C24	1.480 (3)
O55—C52	1.419 (2)	N22—C26	1.488 (3)
O55—H55	0.84	N22—C22	1.496 (3)
C51—C52	1.525 (3)	N22—H22	0.93
C52—C53	1.538 (3)	C21—C22	1.510 (3)
C52—H52	1.00	C21—H21A	0.99
C53—C54	1.508 (3)	C21—H21B	0.99
C53—H53A	0.99	C22—H22A	0.99
C53—H53B	0.99	C22—H22B	0.99
O61—C61	1.255 (2)	C23—C24	1.519 (3)
O62—C61	1.274 (2)	C23—H23A	0.99
O63—C64	1.215 (3)	C23—H23B	0.99
O64—C64	1.320 (3)	C24—H24A	0.99
O64—H64	0.84	C24—H24B	0.99
O65—C62	1.423 (2)	C25—C26	1.520 (3)
O65—H65	0.84	C25—H25A	0.99
C61—C62	1.529 (3)	C25—H25B	0.99
C62—C63	1.531 (3)	C26—H26A	0.99
C62—H62	1.00	C26—H26B	0.99

C34—O34—H34	109.5	C12—N12—C16	108.3 (2)
C32—O35—H35	109.5	C14—N12—H12	109.6
O31—C31—O32	123.6 (2)	C12—N12—H12	109.6
O31—C31—C32	120.4 (2)	C16—N12—H12	109.6
O32—C31—C32	116.1 (2)	N11—C11—C12	109.1 (2)
O35—C32—C31	108.1 (2)	N11—C11—H11A	109.9
O35—C32—C33	112.0 (2)	C12—C11—H11A	109.9
C31—C32—C33	113.1 (2)	N11—C11—H11B	109.9
O35—C32—H32	107.8	C12—C11—H11B	109.9
C31—C32—H32	107.8	H11A—C11—H11B	108.3
C33—C32—H32	107.8	N12—C12—C11	109.9 (2)
C34—C33—C32	111.0 (2)	N12—C12—H12A	109.7
C34—C33—H33A	109.4	C11—C12—H12A	109.7
C32—C33—H33A	109.4	N12—C12—H12B	109.7
C34—C33—H33B	109.4	C11—C12—H12B	109.7
C32—C33—H33B	109.4	H12A—C12—H12B	108.2
H33A—C33—H33B	108.0	N11—C13—C14	108.6 (2)
O33—C34—O34	123.1 (2)	N11—C13—H13A	110.0
O33—C34—C33	123.7 (2)	C14—C13—H13A	110.0
O34—C34—C33	113.2 (2)	N11—C13—H13B	110.0
C44—O44—H44	109.5	C14—C13—H13B	110.0
C42—O45—H45	109.5	H13A—C13—H13B	108.3
O41—C41—O42	123.6 (2)	N12—C14—C13	110.0 (2)
O41—C41—C42	120.2 (2)	N12—C14—H14A	109.7
O42—C41—C42	116.2 (2)	C13—C14—H14A	109.7
O45—C42—C41	108.1 (2)	N12—C14—H14B	109.7
O45—C42—C43	110.8 (2)	C13—C14—H14B	109.7
C41—C42—C43	112.7 (2)	H14A—C14—H14B	108.2
O45—C42—H42	108.4	N11—C15—C16	108.8 (2)
C41—C42—H42	108.4	N11—C15—H15A	109.9
C43—C42—H42	108.4	C16—C15—H15A	109.9
C44—C43—C42	111.5 (2)	N11—C15—H15B	109.9
C44—C43—H43A	109.3	C16—C15—H15B	109.9
C42—C43—H43A	109.3	H15A—C15—H15B	108.3
C44—C43—H43B	109.3	N12—C16—C15	110.1 (2)
C42—C43—H43B	109.3	N12—C16—H16A	109.6
H43A—C43—H43B	108.0	C15—C16—H16A	109.6
O43—C44—O44	123.0 (2)	N12—C16—H16B	109.6
O43—C44—C43	123.7 (2)	C15—C16—H16B	109.6
O44—C44—C43	113.3 (2)	H16A—C16—H16B	108.2
C54—O54—H54	109.5	C25—N21—C21	109.5 (2)
C52—O55—H55	109.5	C25—N21—C23	110.3 (2)
O51—C51—O52	123.7 (2)	C21—N21—C23	109.2 (2)
O51—C51—C52	120.4 (2)	C25—N21—H21	109.3
O52—C51—C52	115.9 (2)	C21—N21—H21	109.3
O55—C52—C51	108.2 (2)	C23—N21—H21	109.3
O55—C52—C53	111.3 (2)	C24—N22—C26	110.2 (2)
C51—C52—C53	112.1 (2)	C24—N22—C22	110.2 (2)
O55—C52—H52	108.4	C26—N22—C22	108.7 (2)
C51—C52—H52	108.4	C24—N22—H22	109.3
C53—C52—H52	108.4	C26—N22—H22	109.3
C54—C53—C52	111.6 (2)	C22—N22—H22	109.3
C54—C53—H53A	109.3	N21—C21—C22	109.3 (2)
C52—C53—H53A	109.3	N21—C21—H21A	109.8
C54—C53—H53B	109.3	C22—C21—H21A	109.8
C52—C53—H53B	109.3	N21—C21—H21B	109.8
H53A—C53—H53B	108.0	C22—C21—H21B	109.8
O53—C54—O54	122.5 (2)	H21A—C21—H21B	108.3
O53—C54—C53	124.3 (2)	N22—C22—C21	109.2 (2)
O54—C54—C53	113.2 (2)	N22—C22—H22A	109.8
C64—O64—H64	109.5	C21—C22—H22A	109.8
C62—O65—H65	109.5	N22—C22—H22B	109.8
O61—C61—O62	124.0 (2)	C21—C22—H22B	109.8
O61—C61—C62	120.0 (2)	H22A—C22—H22B	108.3
O62—C61—C62	115.9 (2)	N21—C23—C24	109.4 (2)
O65—C62—C61	108.4 (2)	N21—C23—H23A	109.8
O65—C62—C63	111.2 (2)	C24—C23—H23A	109.8
C61—C62—C63	113.0 (2)	N21—C23—H23B	109.8
O65—C62—H62	108.0	C24—C23—H23B	109.8
C61—C62—H62	108.0	H23A—C23—H23B	108.2
C63—C62—H62	108.0	N22—C24—C23	109.0 (2)
C64—C63—C62	111.8 (2)	N22—C24—H24A	109.9
C64—C63—H63A	109.3	C23—C24—H24A	109.9
C62—C63—H63A	109.3	N22—C24—H24B	109.9
C64—C63—H63B	109.3	C23—C24—H24B	109.9
C62—C63—H63B	109.3	H24A—C24—H24B	108.3
H63A—C63—H63B	107.9	N21—C25—C26	109.4 (2)
O63—C64—O64	122.5 (2)	N21—C25—H25A	109.8
O63—C64—C63	123.8 (2)	C26—C25—H25A	109.8
O64—C64—C63	113.7 (2)	N21—C25—H25B	109.8
C11—N11—C13	110.0 (2)	C26—C25—H25B	109.8
C11—N11—C15	109.3 (2)	H25A—C25—H25B	108.2
C13—N11—C15	109.2 (2)	N22—C26—C25	108.8 (2)
C11—N11—H11	109.4	N22—C26—H26A	109.9
C13—N11—H11	109.4	C25—C26—H26A	109.9
C15—N11—H11	109.4	N22—C26—H26B	109.9
C14—N12—C12	109.8 (2)	C25—C26—H26B	109.9
C14—N12—C16	109.9 (2)	H26A—C26—H26B	108.3

O31—C31—C32—O35	7.0 (3)	C62—C63—C64—O64	131.2 (2)
O32—C31—C32—O35	−171.1 (2)	C13—N11—C11—C12	62.9 (3)
O31—C31—C32—C33	−117.6 (2)	C15—N11—C11—C12	−57.0 (3)
O32—C31—C32—C33	64.3 (3)	C14—N12—C12—C11	−56.5 (3)
O35—C32—C33—C34	−50.2 (2)	C16—N12—C12—C11	63.6 (3)
C31—C32—C33—C34	72.2 (2)	N11—C11—C12—N12	−5.5 (3)
C32—C33—C34—O33	−53.9 (3)	C11—N11—C13—C14	−56.3 (3)
C32—C33—C34—O34	126.5 (2)	C15—N11—C13—C14	63.6 (3)
O41—C41—C42—O45	7.1 (3)	C12—N12—C14—C13	63.0 (3)
O42—C41—C42—O45	−171.2 (2)	C16—N12—C14—C13	−56.1 (3)
O41—C41—C42—C43	−115.7 (2)	N11—C13—C14—N12	−5.7 (3)
O42—C41—C42—C43	65.9 (3)	C11—N11—C15—C16	62.7 (3)
O45—C42—C43—C44	−49.8 (2)	C13—N11—C15—C16	−57.7 (3)
C41—C42—C43—C44	71.5 (2)	C14—N12—C16—C15	62.3 (3)
C42—C43—C44—O43	−63.1 (3)	C12—N12—C16—C15	−57.8 (3)
C42—C43—C44—O44	115.2 (2)	N11—C15—C16—N12	−4.2 (3)
O51—C51—C52—O55	13.6 (3)	C25—N21—C21—C22	57.0 (3)
O52—C51—C52—O55	−165.8 (2)	C23—N21—C21—C22	−63.9 (3)
O51—C51—C52—C53	−109.6 (2)	C24—N22—C22—C21	56.6 (3)
O52—C51—C52—C53	71.1 (3)	C26—N22—C22—C21	−64.2 (3)
O55—C52—C53—C54	−52.3 (2)	N21—C21—C22—N22	5.9 (3)
C51—C52—C53—C54	69.1 (2)	C25—N21—C23—C24	−62.1 (3)
C52—C53—C54—O53	−57.3 (3)	C21—N21—C23—C24	58.3 (3)
C52—C53—C54—O54	121.3 (2)	C26—N22—C24—C23	57.9 (3)
O61—C61—C62—O65	9.0 (3)	C22—N22—C24—C23	−62.0 (3)
O62—C61—C62—O65	−169.3 (2)	N21—C23—C24—N22	3.9 (3)
O61—C61—C62—C63	−114.7 (2)	C21—N21—C25—C26	−63.4 (3)
O62—C61—C62—C63	67.0 (3)	C23—N21—C25—C26	56.7 (3)
O65—C62—C63—C64	−50.9 (2)	C24—N22—C26—C25	−63.2 (3)
C61—C62—C63—C64	71.3 (2)	C22—N22—C26—C25	57.6 (3)
C62—C63—C64—O63	−48.2 (3)	N21—C25—C26—N22	4.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O31	0.93	1.79	2.634 (2)	150
N12—H12···O51	0.93	1.74	2.610 (2)	154
N21—H21···O61	0.93	1.79	2.631 (2)	148
N22—H22···O41	0.93	1.77	2.629 (2)	153
O34—H34···O52ⁱ	0.84	1.80	2.611 (2)	161
O35—H35···O62ⁱⁱ	0.84	1.88	2.700 (2)	165
O44—H44···O42ⁱⁱⁱ	0.84	1.83	2.631 (2)	160
O45—H45···O32^iv	0.84	1.90	2.709 (2)	161
O54—H54···O32^v	0.84	1.83	2.649 (2)	166
O55—H55···O42^vi	0.84	1.91	2.732 (2)	167
O64—H64···O62^vii	0.84	1.80	2.630 (2)	167
O65—H65···O52	0.84	1.87	2.699 (2)	169
C12—H12B···O44^viii	0.99	2.41	3.252 (3)	143
C15—H15B···O43^ix	0.99	2.34	3.258 (3)	154
C22—H22A···O54^viii	0.99	2.45	3.390 (3)	158
C23—H23B···O32^x	0.99	2.46	3.391 (3)	156
C26—H26B···O33^x	0.99	2.28	3.265 (3)	171

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

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Format		BIBTeX
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		RefMan
		Refer
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		CIF
		SGML
		Text
		Plain Text