Binary co-crystals of the active pharmaceutical ingredient 1,4-bis(4-pyridyl)-2,3-diaza-1,3-butadiene and camphoric acid

Co-crystals comprising the active pharmaceutical ingredient 1,4-bis(4-pyridyl)-2,3-diaza-1,3-butadiene, C₁₂H₁₀N₄, and the chiral co-formers (+)-, (−)- and (rac)-camphoric acid (cam), C₁₀H₁₆O₄, have been synthesized. Two different stoichiometries of the API and co-former are obtained, namely 1:1 and 3:2. Crystallization experiments suggest that the 3:2 co-crystal is kinetically favoured over the 1:1 co-crystal. Single-crystal X-ray diffraction analysis of the co-crystals reveals N—H...O hydrogen bonding as the primary driving force for crystallization of the supramolecular structures. The 1:1 co-crystal contains undulating hydrogen-bonded ribbons, in which the chiral cam molecules impart a helical twist. The 3:2 co-crystal contains discrete Z-shaped motifs comprising three molecules of the API and two molecules of cam. The 3:2 co-crystals with (+)-cam, (−)-cam (space group P2₁) and (rac)-cam (space group P2₁/n) are isostructural. The enantiomeric co-crystals contain pseudo-symmetry consistent with space group P2₁/n, and the co-crystal with (rac)-cam represents a solid solution between the co-crystals containing (+)-cam and (−)-cam.

Computing details

For all compounds, data collection: SMART (Bruker, 2008); cell refinement: SMART; data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97.

Figures

(ccp11)

Crystal data

C12H10N4·C10H16O4	F(000) = 872
Mr = 410.47	Dx = 1.306 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5868 reflections
a = 7.2598 (11) Å	θ = 2.5–28.2°
b = 10.2744 (15) Å	µ = 0.09 mm^−1
c = 27.997 (4) Å	T = 150 K
V = 2088.3 (5) Å^3	Plate, yellow
Z = 4	0.23 × 0.11 × 0.09 mm

Data collection

Bruker SMART APEX CCD diffractometer	4834 independent reflections
Radiation source: fine-focus sealed tube	4686 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω and φ scans	θmax = 28.0°, θmin = 1.5°
Absorption correction: multi-scan SADABS (Bruker, 2008)	h = −9→9
Tmin = 0.979, Tmax = 0.992	k = −12→13
12500 measured reflections	l = −21→36

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0482P)^2 + 0.7672P] where P = (Fo^2 + 2Fc^2)/3
4834 reflections	(Δ/σ)max < 0.001
282 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
N1	0.0406 (2)	0.88912 (16)	0.13837 (6)	0.0195 (3)
N2	0.6433 (2)	0.87659 (16)	0.22967 (6)	0.0201 (3)
N3	0.8147 (2)	0.92533 (16)	0.24548 (6)	0.0209 (4)
N4	1.4240 (2)	0.95420 (16)	0.32922 (6)	0.0187 (3)
C1	0.2888 (3)	0.81464 (18)	0.18764 (6)	0.0183 (4)
H1	0.3371	0.7493	0.2081	0.022*
C2	0.1182 (3)	0.79962 (19)	0.16671 (7)	0.0198 (4)
H2	0.0522	0.7215	0.1727	0.024*
C3	0.1362 (3)	0.99764 (19)	0.12946 (7)	0.0219 (4)
H3	0.0827	1.0619	0.1094	0.026*
C4	0.3101 (3)	1.02048 (19)	0.14820 (7)	0.0212 (4)
H4	0.3743	1.0984	0.1407	0.025*
C5	0.3894 (3)	0.92800 (18)	0.17812 (7)	0.0184 (4)
C6	0.5714 (3)	0.95315 (19)	0.19909 (7)	0.0211 (4)
H6	0.6374	1.0287	0.1896	0.025*
C7	0.8892 (3)	0.85399 (18)	0.27737 (6)	0.0177 (4)
H7	0.8273	0.7788	0.2889	0.021*
C8	1.0727 (3)	0.88954 (18)	0.29613 (6)	0.0172 (4)
C9	1.1548 (3)	1.00770 (18)	0.28402 (7)	0.0182 (4)
H9	1.0922	1.0679	0.2640	0.022*
C10	1.3282 (3)	1.03615 (19)	0.30142 (7)	0.0202 (4)
H10	1.3821	1.1175	0.2933	0.024*
C11	1.3447 (3)	0.84079 (19)	0.34080 (7)	0.0204 (4)
H11	1.4112	0.7821	0.3606	0.024*
C12	1.1707 (3)	0.80469 (18)	0.32546 (7)	0.0194 (4)
H12	1.1191	0.7236	0.3348	0.023*
O1	0.2655 (2)	0.52565 (13)	0.12468 (5)	0.0209 (3)
H1C	0.353 (4)	0.500 (2)	0.1422 (9)	0.033 (7)*
O2	0.2392 (2)	0.31321 (13)	0.10887 (5)	0.0225 (3)
O3	0.2399 (2)	0.63474 (13)	−0.08384 (5)	0.0222 (3)
H3C	0.324 (4)	0.624 (3)	−0.1045 (10)	0.047 (8)*
O4	0.2176 (2)	0.41848 (13)	−0.09293 (5)	0.0215 (3)
C13	0.2005 (3)	0.42547 (18)	0.09968 (6)	0.0162 (4)
C14	0.0764 (2)	0.46710 (17)	0.05834 (6)	0.0143 (3)
C15	0.0027 (3)	0.34745 (18)	0.03156 (7)	0.0176 (4)
H15A	−0.1045	0.3096	0.0485	0.021*
H15B	0.0993	0.2800	0.0285	0.021*
C16	−0.0540 (3)	0.39916 (19)	−0.01778 (7)	0.0197 (4)
H16A	−0.1868	0.4211	−0.0182	0.024*
H16B	−0.0296	0.3332	−0.0428	0.024*
C17	0.0642 (2)	0.52248 (17)	−0.02638 (6)	0.0150 (3)
H17	−0.0207	0.5989	−0.0289	0.018*
C18	0.1792 (3)	0.51700 (18)	−0.07144 (7)	0.0164 (4)
C19	0.1896 (2)	0.54201 (17)	0.01911 (6)	0.0147 (4)
C20	−0.0848 (3)	0.54934 (18)	0.07751 (7)	0.0181 (4)
H20A	−0.1607	0.4961	0.0989	0.027*
H20B	−0.1600	0.5801	0.0507	0.027*
H20C	−0.0362	0.6242	0.0952	0.027*
C21	0.3811 (3)	0.47884 (19)	0.01256 (7)	0.0201 (4)
H21A	0.4524	0.4882	0.0421	0.030*
H21B	0.4463	0.5220	−0.0137	0.030*
H21C	0.3662	0.3862	0.0051	0.030*
C22	0.2186 (3)	0.68729 (18)	0.02948 (7)	0.0196 (4)
H22A	0.2837	0.7277	0.0026	0.029*
H22B	0.2919	0.6972	0.0587	0.029*
H22C	0.0988	0.7297	0.0338	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0190 (8)	0.0239 (8)	0.0155 (8)	0.0023 (7)	−0.0020 (6)	−0.0007 (6)
N2	0.0175 (8)	0.0242 (8)	0.0188 (8)	−0.0001 (7)	−0.0012 (6)	−0.0028 (7)
N3	0.0171 (8)	0.0250 (8)	0.0205 (8)	−0.0005 (7)	−0.0023 (6)	−0.0008 (7)
N4	0.0156 (7)	0.0244 (8)	0.0160 (8)	0.0005 (6)	0.0006 (6)	−0.0034 (6)
C1	0.0217 (9)	0.0172 (8)	0.0160 (9)	0.0036 (7)	−0.0003 (7)	−0.0004 (7)
C2	0.0200 (9)	0.0193 (9)	0.0202 (9)	−0.0018 (7)	0.0009 (8)	−0.0033 (7)
C3	0.0212 (9)	0.0238 (10)	0.0205 (9)	0.0049 (8)	−0.0017 (8)	0.0028 (8)
C4	0.0212 (9)	0.0194 (9)	0.0229 (10)	−0.0016 (8)	0.0008 (8)	0.0028 (8)
C5	0.0185 (9)	0.0218 (9)	0.0149 (9)	0.0019 (7)	0.0001 (7)	−0.0036 (7)
C6	0.0204 (9)	0.0227 (10)	0.0201 (9)	−0.0021 (8)	0.0001 (8)	−0.0001 (7)
C7	0.0187 (9)	0.0188 (9)	0.0155 (9)	−0.0013 (7)	0.0009 (7)	−0.0025 (7)
C8	0.0171 (9)	0.0216 (9)	0.0129 (8)	0.0030 (7)	0.0009 (7)	−0.0045 (7)
C9	0.0200 (9)	0.0184 (9)	0.0162 (9)	0.0020 (7)	−0.0015 (7)	0.0015 (7)
C10	0.0227 (9)	0.0191 (9)	0.0188 (9)	−0.0024 (8)	0.0032 (8)	0.0001 (7)
C11	0.0200 (9)	0.0225 (9)	0.0188 (9)	0.0060 (7)	−0.0015 (7)	−0.0007 (7)
C12	0.0211 (9)	0.0174 (8)	0.0197 (9)	−0.0002 (7)	0.0010 (8)	−0.0006 (7)
O1	0.0223 (7)	0.0198 (6)	0.0206 (7)	0.0028 (6)	−0.0074 (6)	−0.0005 (5)
O2	0.0262 (7)	0.0179 (6)	0.0234 (7)	0.0011 (6)	−0.0060 (6)	0.0048 (5)
O3	0.0257 (7)	0.0197 (6)	0.0213 (7)	−0.0006 (6)	0.0086 (6)	0.0019 (5)
O4	0.0230 (7)	0.0215 (7)	0.0200 (7)	−0.0013 (6)	0.0027 (6)	−0.0045 (5)
C13	0.0147 (8)	0.0188 (8)	0.0151 (9)	−0.0005 (7)	0.0029 (7)	−0.0001 (7)
C14	0.0149 (8)	0.0133 (8)	0.0148 (8)	0.0003 (7)	0.0009 (7)	0.0007 (6)
C15	0.0194 (9)	0.0152 (8)	0.0181 (9)	−0.0031 (7)	0.0006 (7)	0.0004 (7)
C16	0.0184 (9)	0.0226 (9)	0.0180 (9)	−0.0072 (7)	−0.0008 (7)	0.0005 (7)
C17	0.0130 (8)	0.0161 (8)	0.0158 (8)	0.0005 (7)	0.0016 (7)	−0.0001 (7)
C18	0.0141 (8)	0.0207 (9)	0.0145 (8)	0.0005 (7)	−0.0010 (7)	0.0024 (7)
C19	0.0129 (8)	0.0155 (8)	0.0157 (9)	−0.0010 (7)	0.0014 (7)	0.0003 (7)
C20	0.0184 (9)	0.0193 (9)	0.0168 (9)	0.0038 (7)	0.0031 (8)	0.0015 (7)
C21	0.0131 (8)	0.0262 (9)	0.0209 (9)	0.0028 (7)	−0.0005 (7)	0.0003 (8)
C22	0.0220 (10)	0.0172 (8)	0.0195 (9)	−0.0037 (8)	0.0006 (8)	0.0000 (7)

Geometric parameters (Å, º)

N1—C3	1.337 (3)	O2—C13	1.215 (2)
N1—C2	1.339 (3)	O3—C18	1.333 (2)
N2—C6	1.274 (3)	O3—H3C	0.85 (3)
N2—N3	1.413 (2)	O4—C18	1.210 (2)
N3—C7	1.275 (3)	C13—C14	1.528 (2)
N4—C11	1.340 (3)	C14—C15	1.536 (2)
N4—C10	1.341 (3)	C14—C20	1.540 (2)
C1—C2	1.379 (3)	C14—C19	1.573 (2)
C1—C5	1.401 (3)	C15—C16	1.536 (3)
C1—H1	0.9500	C15—H15A	0.9900
C2—H2	0.9500	C15—H15B	0.9900
C3—C4	1.387 (3)	C16—C17	1.549 (2)
C3—H3	0.9500	C16—H16A	0.9900
C4—C5	1.391 (3)	C16—H16B	0.9900
C4—H4	0.9500	C17—C18	1.514 (2)
C5—C6	1.469 (3)	C17—C19	1.578 (3)
C6—H6	0.9500	C17—H17	1.0000
C7—C8	1.478 (3)	C19—C22	1.535 (2)
C7—H7	0.9500	C19—C21	1.546 (3)
C8—C12	1.393 (3)	C20—H20A	0.9800
C8—C9	1.394 (3)	C20—H20B	0.9800
C9—C10	1.381 (3)	C20—H20C	0.9800
C9—H9	0.9500	C21—H21A	0.9800
C10—H10	0.9500	C21—H21B	0.9800
C11—C12	1.385 (3)	C21—H21C	0.9800
C11—H11	0.9500	C22—H22A	0.9800
C12—H12	0.9500	C22—H22B	0.9800
O1—C13	1.331 (2)	C22—H22C	0.9800
O1—H1C	0.85 (3)
C3—N1—C2	117.69 (17)	C13—C14—C19	110.96 (14)
C6—N2—N3	110.64 (16)	C15—C14—C19	103.47 (14)
C7—N3—N2	112.89 (16)	C20—C14—C19	111.83 (14)
C11—N4—C10	117.62 (17)	C14—C15—C16	104.80 (14)
C2—C1—C5	118.74 (18)	C14—C15—H15A	110.8
C2—C1—H1	120.6	C16—C15—H15A	110.8
C5—C1—H1	120.6	C14—C15—H15B	110.8
N1—C2—C1	123.59 (18)	C16—C15—H15B	110.8
N1—C2—H2	118.2	H15A—C15—H15B	108.9
C1—C2—H2	118.2	C15—C16—C17	105.92 (15)
N1—C3—C4	122.90 (18)	C15—C16—H16A	110.6
N1—C3—H3	118.6	C17—C16—H16A	110.6
C4—C3—H3	118.6	C15—C16—H16B	110.6
C3—C4—C5	119.27 (18)	C17—C16—H16B	110.6
C3—C4—H4	120.4	H16A—C16—H16B	108.7
C5—C4—H4	120.4	C18—C17—C16	113.87 (15)
C4—C5—C1	117.80 (18)	C18—C17—C19	111.03 (15)
C4—C5—C6	119.54 (18)	C16—C17—C19	107.34 (14)
C1—C5—C6	122.65 (17)	C18—C17—H17	108.1
N2—C6—C5	121.89 (18)	C16—C17—H17	108.1
N2—C6—H6	119.1	C19—C17—H17	108.1
C5—C6—H6	119.1	O4—C18—O3	123.60 (17)
N3—C7—C8	119.25 (17)	O4—C18—C17	124.93 (16)
N3—C7—H7	120.4	O3—C18—C17	111.43 (15)
C8—C7—H7	120.4	C22—C19—C21	107.88 (15)
C12—C8—C9	118.02 (18)	C22—C19—C14	114.56 (15)
C12—C8—C7	121.01 (17)	C21—C19—C14	110.33 (14)
C9—C8—C7	120.95 (17)	C22—C19—C17	110.82 (15)
C10—C9—C8	119.23 (18)	C21—C19—C17	111.70 (14)
C10—C9—H9	120.4	C14—C19—C17	101.53 (13)
C8—C9—H9	120.4	C14—C20—H20A	109.5
N4—C10—C9	122.99 (18)	C14—C20—H20B	109.5
N4—C10—H10	118.5	H20A—C20—H20B	109.5
C9—C10—H10	118.5	C14—C20—H20C	109.5
N4—C11—C12	123.38 (18)	H20A—C20—H20C	109.5
N4—C11—H11	118.3	H20B—C20—H20C	109.5
C12—C11—H11	118.3	C19—C21—H21A	109.5
C11—C12—C8	118.76 (18)	C19—C21—H21B	109.5
C11—C12—H12	120.6	H21A—C21—H21B	109.5
C8—C12—H12	120.6	C19—C21—H21C	109.5
C13—O1—H1C	109.2 (17)	H21A—C21—H21C	109.5
C18—O3—H3C	107 (2)	H21B—C21—H21C	109.5
O2—C13—O1	122.76 (17)	C19—C22—H22A	109.5
O2—C13—C14	124.23 (16)	C19—C22—H22B	109.5
O1—C13—C14	113.01 (15)	H22A—C22—H22B	109.5
C13—C14—C15	110.56 (14)	C19—C22—H22C	109.5
C13—C14—C20	109.74 (14)	H22A—C22—H22C	109.5
C15—C14—C20	110.15 (15)	H22B—C22—H22C	109.5
C6—N2—N3—C7	177.80 (17)	O2—C13—C14—C19	−112.1 (2)
C3—N1—C2—C1	1.2 (3)	O1—C13—C14—C19	66.97 (19)
C5—C1—C2—N1	−1.5 (3)	C13—C14—C15—C16	−159.19 (15)
C2—N1—C3—C4	0.0 (3)	C20—C14—C15—C16	79.35 (18)
N1—C3—C4—C5	−0.8 (3)	C19—C14—C15—C16	−40.33 (18)
C3—C4—C5—C1	0.4 (3)	C14—C15—C16—C17	25.12 (19)
C3—C4—C5—C6	−178.39 (17)	C15—C16—C17—C18	122.90 (17)
C2—C1—C5—C4	0.7 (3)	C15—C16—C17—C19	−0.42 (19)
C2—C1—C5—C6	179.43 (17)	C16—C17—C18—O4	−18.5 (3)
N3—N2—C6—C5	−177.75 (16)	C19—C17—C18—O4	102.8 (2)
C4—C5—C6—N2	174.22 (19)	C16—C17—C18—O3	163.84 (16)
C1—C5—C6—N2	−4.5 (3)	C19—C17—C18—O3	−74.87 (19)
N2—N3—C7—C8	177.63 (15)	C13—C14—C19—C22	−83.18 (18)
N3—C7—C8—C12	−170.28 (18)	C15—C14—C19—C22	158.23 (15)
N3—C7—C8—C9	8.1 (3)	C20—C14—C19—C22	39.7 (2)
C12—C8—C9—C10	−0.1 (3)	C13—C14—C19—C21	38.78 (19)
C7—C8—C9—C10	−178.56 (16)	C15—C14—C19—C21	−79.81 (17)
C11—N4—C10—C9	−0.9 (3)	C20—C14—C19—C21	161.67 (15)
C8—C9—C10—N4	0.9 (3)	C13—C14—C19—C17	157.34 (14)
C10—N4—C11—C12	0.2 (3)	C15—C14—C19—C17	38.75 (16)
N4—C11—C12—C8	0.6 (3)	C20—C14—C19—C17	−79.77 (17)
C9—C8—C12—C11	−0.6 (3)	C18—C17—C19—C22	89.36 (18)
C7—C8—C12—C11	177.88 (17)	C16—C17—C19—C22	−145.59 (15)
O2—C13—C14—C15	2.1 (3)	C18—C17—C19—C21	−30.96 (19)
O1—C13—C14—C15	−178.81 (15)	C16—C17—C19—C21	94.09 (17)
O2—C13—C14—C20	123.8 (2)	C18—C17—C19—C14	−148.53 (14)
O1—C13—C14—C20	−57.11 (19)	C16—C17—C19—C14	−23.49 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···N4^i	0.85 (3)	1.86 (3)	2.699 (2)	169 (3)
O3—H3C···N1^ii	0.85 (3)	1.84 (3)	2.675 (2)	167 (3)

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

(ccp32)

Crystal data

3(C12H10N4)·2(C10H16O4)	F(000) = 1092
Mr = 1031.18	Dx = 1.325 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4895 reflections
a = 9.9568 (17) Å	θ = 2.4–28.1°
b = 12.914 (2) Å	µ = 0.09 mm^−1
c = 20.203 (4) Å	T = 110 K
β = 95.734 (3)°	Block, yellow
V = 2584.7 (8) Å^3	0.68 × 0.48 × 0.10 mm
Z = 2

Data collection

Bruker SMART APEX CCD diffractometer	9631 independent reflections
Radiation source: fine-focus sealed tube	8918 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
ω and φ scans	θmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan SADABS (Bruker, 2008)	h = −10→12
Tmin = 0.941, Tmax = 0.991	k = −15→16
12491 measured reflections	l = −25→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.178	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0847P)^2 + 1.6575P] where P = (Fo^2 + 2Fc^2)/3
9631 reflections	(Δ/σ)max = 0.001
695 parameters	Δρmax = 0.39 e Å^−3
1 restraint	Δρmin = −0.29 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1	1.2428 (2)	0.6358 (2)	0.46591 (12)	0.0213 (6)
H1C	1.2846	0.6736	0.4427	0.032*
O2	1.0961 (3)	0.6341 (3)	0.37576 (13)	0.0369 (8)
O3	0.8226 (3)	0.5275 (2)	0.64989 (12)	0.0277 (7)
O4	0.6638 (3)	0.5436 (3)	0.56443 (12)	0.0295 (7)
H4C	0.6201	0.5680	0.5930	0.044*
O5	0.6886 (3)	0.4666 (3)	0.85365 (13)	0.0312 (7)
O6	0.8385 (2)	0.4669 (3)	0.94262 (13)	0.0275 (7)
H6C	0.8878	0.4440	0.9159	0.041*
O7	0.2698 (2)	0.3594 (2)	1.03924 (12)	0.0236 (6)
H7C	0.2258	0.3260	1.0640	0.035*
O8	0.4103 (3)	0.3809 (2)	1.13210 (12)	0.0262 (6)
N1	−0.1893 (4)	1.1378 (3)	0.9240 (2)	0.0383 (9)
N2	0.1174 (3)	0.9157 (3)	0.80028 (17)	0.0307 (8)
N3	0.1737 (3)	0.8654 (3)	0.74784 (17)	0.0295 (8)
N4	0.5106 (3)	0.6357 (3)	0.64606 (16)	0.0253 (8)
N5	0.6086 (3)	0.2565 (2)	0.60750 (14)	0.0170 (6)
N6	0.2791 (3)	0.4743 (3)	0.72367 (15)	0.0196 (7)
N7	0.2335 (3)	0.5324 (3)	0.77666 (15)	0.0179 (7)
N8	−0.1069 (3)	0.7468 (3)	0.88922 (16)	0.0224 (7)
N9	0.6933 (4)	−0.1350 (3)	0.59125 (18)	0.0343 (9)
N10	0.3850 (3)	0.0986 (3)	0.70498 (16)	0.0247 (7)
N11	0.3252 (3)	0.1482 (3)	0.75705 (15)	0.0241 (7)
N12	−0.0144 (3)	0.3692 (3)	0.86052 (16)	0.0263 (8)
C1	−0.1544 (4)	1.1012 (4)	0.8099 (2)	0.0325 (10)
H1	−0.1794	1.1144	0.7651	0.039*
C2	−0.2155 (4)	1.1532 (3)	0.8591 (3)	0.0370 (11)
H2	−0.2801	1.2028	0.8454	0.044*
C3	−0.0942 (4)	1.0673 (3)	0.9420 (2)	0.0291 (9)
H3	−0.0724	1.0556	0.9872	0.035*
C4	−0.0266 (4)	1.0112 (4)	0.8980 (2)	0.0274 (9)
H4	0.0371	0.9619	0.9134	0.033*
C5	−0.0548 (4)	1.0292 (3)	0.8295 (2)	0.0282 (9)
C6	0.0180 (4)	0.9731 (4)	0.7808 (2)	0.0287 (9)
H6	−0.0090	0.9798	0.7356	0.034*
C7	0.2843 (4)	0.8212 (3)	0.76873 (19)	0.0249 (9)
H7	0.3174	0.8281	0.8132	0.030*
C8	0.3606 (4)	0.7594 (3)	0.7242 (2)	0.0230 (8)
C9	0.4763 (4)	0.7073 (3)	0.75123 (18)	0.0224 (8)
H9	0.5050	0.7128	0.7963	0.027*
C10	0.5475 (4)	0.6475 (3)	0.71020 (19)	0.0231 (8)
H10	0.6251	0.6139	0.7286	0.028*
C11	0.3987 (4)	0.6856 (4)	0.62037 (19)	0.0290 (10)
H11	0.3717	0.6781	0.5752	0.035*
C12	0.3226 (4)	0.7466 (4)	0.65752 (19)	0.0273 (9)
H12	0.2455	0.7793	0.6377	0.033*
C13	0.5971 (3)	0.3409 (3)	0.71182 (18)	0.0208 (8)
H13	0.6388	0.3568	0.7538	0.025*
C14	0.6639 (4)	0.2830 (3)	0.66847 (18)	0.0221 (8)
H14	0.7514	0.2613	0.6819	0.027*
C15	0.4828 (4)	0.2887 (3)	0.58927 (17)	0.0175 (7)
H15	0.4431	0.2707	0.5472	0.021*
C16	0.4086 (3)	0.3476 (3)	0.62980 (17)	0.0179 (8)
H16	0.3211	0.3682	0.6153	0.021*
C17	0.4674 (3)	0.3753 (3)	0.69260 (17)	0.0152 (7)
C18	0.3977 (3)	0.4375 (3)	0.73973 (17)	0.0174 (8)
H18	0.4404	0.4505	0.7820	0.021*
C19	0.1171 (3)	0.5698 (3)	0.75995 (17)	0.0177 (8)
H19	0.0765	0.5581	0.7171	0.021*
C20	0.0442 (3)	0.6313 (3)	0.80636 (17)	0.0167 (7)
C21	−0.0866 (3)	0.6630 (3)	0.78496 (18)	0.0206 (8)
H21	−0.1262	0.6462	0.7427	0.025*
C22	−0.1567 (4)	0.7208 (3)	0.82872 (19)	0.0224 (8)
H22	−0.2438	0.7423	0.8142	0.027*
C23	0.0198 (3)	0.7167 (3)	0.90946 (18)	0.0213 (8)
H23	0.0569	0.7356	0.9518	0.026*
C24	0.0976 (4)	0.6585 (3)	0.86985 (18)	0.0216 (8)
H24	0.1844	0.6381	0.8858	0.026*
C25	0.6610 (4)	−0.0848 (4)	0.7025 (2)	0.0309 (9)
H25	0.6858	−0.0930	0.7478	0.037*
C26	0.7245 (4)	−0.1413 (4)	0.6563 (2)	0.0337 (10)
H26	0.7933	−0.1864	0.6720	0.040*
C27	0.5969 (4)	−0.0680 (4)	0.5700 (2)	0.0330 (10)
H27	0.5748	−0.0618	0.5244	0.040*
C28	0.5274 (4)	−0.0071 (3)	0.61141 (19)	0.0250 (9)
H28	0.4609	0.0385	0.5938	0.030*
C29	0.5589 (4)	−0.0152 (3)	0.67975 (19)	0.0226 (8)
C30	0.4859 (4)	0.0424 (3)	0.72710 (18)	0.0224 (8)
H30	0.5122	0.0384	0.7725	0.027*
C31	0.2160 (4)	0.1917 (3)	0.7350 (2)	0.0243 (9)
H31	0.1863	0.1862	0.6900	0.029*
C32	0.1350 (4)	0.2507 (3)	0.77874 (18)	0.0191 (8)
C33	0.0279 (4)	0.3116 (3)	0.75205 (18)	0.0222 (8)
H33	0.0040	0.3134	0.7064	0.027*
C34	−0.0422 (4)	0.3693 (3)	0.7947 (2)	0.0257 (9)
H34	−0.1129	0.4106	0.7764	0.031*
C35	0.0883 (4)	0.3087 (4)	0.88620 (19)	0.0297 (10)
H35	0.1089	0.3076	0.9321	0.036*
C36	0.1642 (4)	0.2485 (3)	0.8475 (2)	0.0254 (9)
H36	0.2336	0.2071	0.8671	0.030*
C37	0.7851 (3)	0.5208 (3)	0.59085 (19)	0.0203 (8)
C38	0.8773 (3)	0.4842 (3)	0.53852 (16)	0.0149 (7)
C39	1.0106 (3)	0.4350 (3)	0.56976 (17)	0.0187 (7)
H39A	1.0344	0.4622	0.6141	0.022*
H39B	1.0014	0.3604	0.5726	0.022*
C40	1.1200 (3)	0.4635 (3)	0.52369 (16)	0.0154 (6)
H40A	1.1920	0.5030	0.5477	0.019*
H40B	1.1583	0.4015	0.5060	0.019*
C41	1.0473 (3)	0.5285 (3)	0.46752 (17)	0.0160 (7)
H41	1.0070	0.4797	0.4340	0.019*
C42	1.1301 (4)	0.6047 (3)	0.43149 (17)	0.0199 (8)
C43	0.9273 (3)	0.5810 (3)	0.50009 (17)	0.0170 (7)
C44	0.7998 (4)	0.4074 (3)	0.49226 (18)	0.0230 (8)
H44A	0.7730	0.3494	0.5176	0.035*
H44B	0.8564	0.3838	0.4595	0.035*
H44C	0.7211	0.4404	0.4704	0.035*
C45	0.9794 (3)	0.6662 (3)	0.54842 (17)	0.0184 (7)
H45A	1.0230	0.7189	0.5247	0.028*
H45B	1.0429	0.6372	0.5823	0.028*
H45C	0.9051	0.6960	0.5686	0.028*
C46	0.8229 (3)	0.6279 (3)	0.44886 (18)	0.0234 (8)
H46A	0.7474	0.6523	0.4706	0.035*
H46B	0.7928	0.5763	0.4165	0.035*
H46C	0.8624	0.6848	0.4271	0.035*
C47	0.7162 (4)	0.4826 (3)	0.91225 (17)	0.0180 (8)
C48	0.6130 (3)	0.5179 (3)	0.95726 (16)	0.0156 (7)
C49	0.6635 (4)	0.5694 (3)	1.02424 (19)	0.0279 (9)
H49A	0.6749	0.6434	1.0185	0.033*
H49B	0.7493	0.5400	1.0419	0.033*
C50	0.5516 (4)	0.5472 (3)	1.07278 (18)	0.0277 (8)
H50A	0.5904	0.5138	1.1133	0.033*
H50B	0.5077	0.6108	1.0843	0.033*
C51	0.4522 (3)	0.4754 (3)	1.03298 (16)	0.0151 (7)
H51	0.3840	0.5194	1.0085	0.018*
C52	0.3776 (3)	0.4004 (3)	1.07447 (18)	0.0169 (7)
C53	0.5329 (4)	0.4224 (3)	0.98113 (18)	0.0220 (8)
C54	0.5194 (4)	0.5952 (3)	0.9176 (2)	0.0291 (9)
H54A	0.5705	0.6549	0.9068	0.044*
H54B	0.4489	0.6161	0.9438	0.044*
H54C	0.4805	0.5630	0.8773	0.044*
C55	0.6250 (4)	0.3407 (3)	1.0125 (2)	0.0327 (9)
H55A	0.6763	0.3110	0.9795	0.049*
H55B	0.5725	0.2876	1.0310	0.049*
H55C	0.6853	0.3711	1.0472	0.049*
C56	0.4404 (4)	0.3727 (3)	0.92377 (19)	0.0312 (9)
H56A	0.4937	0.3517	0.8891	0.047*
H56B	0.3740	0.4222	0.9065	0.047*
H56C	0.3960	0.3133	0.9402	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0247 (13)	0.0231 (15)	0.0171 (12)	−0.0045 (11)	0.0075 (10)	0.0028 (12)
O2	0.0354 (15)	0.051 (2)	0.0237 (15)	−0.0113 (14)	0.0024 (12)	0.0165 (15)
O3	0.0366 (15)	0.0356 (18)	0.0121 (12)	−0.0042 (13)	0.0086 (10)	−0.0037 (12)
O4	0.0279 (14)	0.042 (2)	0.0203 (13)	0.0019 (13)	0.0121 (11)	−0.0077 (13)
O5	0.0330 (14)	0.0398 (19)	0.0223 (14)	−0.0034 (13)	0.0106 (11)	−0.0072 (13)
O6	0.0170 (12)	0.0339 (18)	0.0327 (14)	−0.0018 (12)	0.0079 (10)	−0.0120 (14)
O7	0.0251 (13)	0.0265 (16)	0.0203 (13)	−0.0094 (11)	0.0083 (10)	0.0036 (12)
O8	0.0254 (13)	0.0361 (18)	0.0171 (13)	−0.0031 (12)	0.0026 (10)	0.0117 (12)
N1	0.044 (2)	0.027 (2)	0.045 (2)	0.0048 (17)	0.0105 (17)	−0.0067 (18)
N2	0.0387 (19)	0.027 (2)	0.0286 (18)	0.0020 (16)	0.0151 (15)	−0.0007 (17)
N3	0.0296 (18)	0.030 (2)	0.0298 (18)	−0.0008 (15)	0.0085 (14)	−0.0003 (17)
N4	0.0229 (15)	0.025 (2)	0.0301 (17)	−0.0044 (14)	0.0122 (13)	−0.0047 (16)
N5	0.0199 (14)	0.0147 (17)	0.0179 (15)	−0.0014 (12)	0.0094 (12)	0.0010 (13)
N6	0.0234 (15)	0.0170 (17)	0.0190 (15)	−0.0046 (13)	0.0044 (12)	−0.0039 (14)
N7	0.0161 (14)	0.0195 (18)	0.0194 (15)	0.0004 (12)	0.0078 (11)	−0.0065 (13)
N8	0.0250 (15)	0.0181 (18)	0.0256 (17)	0.0006 (13)	0.0090 (13)	−0.0024 (14)
N9	0.050 (2)	0.022 (2)	0.035 (2)	0.0025 (16)	0.0246 (16)	0.0028 (16)
N10	0.0260 (16)	0.0245 (19)	0.0243 (16)	0.0022 (14)	0.0065 (13)	−0.0066 (15)
N11	0.0315 (17)	0.023 (2)	0.0196 (15)	0.0019 (15)	0.0115 (13)	−0.0040 (15)
N12	0.0250 (16)	0.031 (2)	0.0236 (16)	−0.0041 (14)	0.0057 (13)	−0.0092 (16)
C1	0.032 (2)	0.023 (2)	0.042 (2)	0.0028 (17)	0.0028 (18)	0.007 (2)
C2	0.032 (2)	0.014 (2)	0.065 (3)	0.0109 (17)	0.003 (2)	−0.003 (2)
C3	0.030 (2)	0.019 (2)	0.040 (2)	0.0014 (16)	0.0059 (17)	0.0005 (19)
C4	0.0196 (17)	0.026 (2)	0.037 (2)	−0.0024 (16)	−0.0001 (16)	0.0002 (19)
C5	0.0232 (19)	0.020 (2)	0.043 (2)	−0.0037 (16)	0.0116 (16)	−0.0058 (19)
C6	0.0256 (19)	0.029 (2)	0.033 (2)	−0.0038 (17)	0.0083 (16)	−0.0038 (19)
C7	0.034 (2)	0.021 (2)	0.0205 (18)	−0.0073 (17)	0.0086 (16)	−0.0025 (18)
C8	0.0197 (18)	0.020 (2)	0.030 (2)	−0.0071 (15)	0.0082 (15)	0.0024 (17)
C9	0.0228 (17)	0.028 (2)	0.0164 (17)	−0.0136 (16)	0.0030 (14)	−0.0055 (16)
C10	0.0209 (17)	0.023 (2)	0.0251 (19)	−0.0070 (15)	0.0005 (14)	−0.0016 (17)
C11	0.039 (2)	0.034 (3)	0.0147 (17)	−0.0046 (18)	0.0044 (16)	0.0000 (17)
C12	0.035 (2)	0.028 (2)	0.0207 (19)	0.0016 (17)	0.0084 (16)	0.0083 (18)
C13	0.0147 (16)	0.027 (2)	0.0205 (17)	0.0024 (15)	0.0015 (13)	0.0027 (17)
C14	0.0210 (18)	0.023 (2)	0.0228 (19)	0.0035 (15)	0.0059 (15)	−0.0011 (17)
C15	0.0287 (18)	0.0143 (19)	0.0099 (16)	−0.0031 (15)	0.0037 (14)	0.0022 (15)
C16	0.0185 (17)	0.018 (2)	0.0174 (17)	0.0022 (14)	0.0028 (13)	0.0047 (16)
C17	0.0194 (16)	0.0113 (19)	0.0153 (16)	−0.0008 (14)	0.0031 (13)	0.0015 (15)
C18	0.0177 (16)	0.019 (2)	0.0163 (17)	−0.0028 (14)	0.0055 (13)	−0.0014 (15)
C19	0.0230 (17)	0.016 (2)	0.0142 (16)	−0.0012 (14)	0.0022 (13)	−0.0058 (15)
C20	0.0191 (16)	0.0107 (19)	0.0216 (17)	0.0005 (13)	0.0083 (13)	0.0011 (16)
C21	0.0220 (17)	0.020 (2)	0.0195 (17)	−0.0016 (15)	0.0014 (14)	−0.0075 (16)
C22	0.0195 (17)	0.020 (2)	0.028 (2)	0.0038 (15)	0.0033 (15)	−0.0026 (18)
C23	0.0194 (17)	0.024 (2)	0.0203 (18)	0.0012 (15)	0.0004 (14)	−0.0051 (17)
C24	0.0209 (18)	0.024 (2)	0.0211 (18)	−0.0017 (16)	0.0060 (14)	−0.0003 (17)
C25	0.036 (2)	0.026 (2)	0.032 (2)	−0.0020 (18)	0.0121 (17)	0.0004 (19)
C26	0.044 (2)	0.026 (2)	0.035 (2)	0.0074 (19)	0.0185 (18)	0.0084 (19)
C27	0.043 (2)	0.033 (3)	0.025 (2)	−0.008 (2)	0.0136 (18)	−0.0075 (19)
C28	0.031 (2)	0.017 (2)	0.029 (2)	−0.0049 (16)	0.0132 (16)	−0.0036 (17)
C29	0.0280 (19)	0.013 (2)	0.0283 (19)	−0.0064 (15)	0.0102 (15)	0.0010 (16)
C30	0.0313 (19)	0.019 (2)	0.0172 (17)	−0.0053 (16)	0.0060 (14)	−0.0005 (16)
C31	0.0256 (19)	0.027 (2)	0.0215 (18)	−0.0046 (16)	0.0093 (15)	0.0007 (18)
C32	0.0246 (18)	0.016 (2)	0.0177 (17)	−0.0035 (15)	0.0072 (14)	−0.0013 (16)
C33	0.0274 (19)	0.027 (2)	0.0127 (17)	−0.0054 (16)	0.0039 (14)	0.0034 (16)
C34	0.0182 (17)	0.022 (2)	0.038 (2)	0.0000 (15)	0.0086 (15)	0.0046 (19)
C35	0.028 (2)	0.045 (3)	0.0167 (18)	0.0027 (18)	0.0057 (15)	−0.0064 (19)
C36	0.0257 (18)	0.025 (2)	0.026 (2)	0.0026 (16)	0.0053 (15)	−0.0005 (18)
C37	0.0195 (17)	0.014 (2)	0.028 (2)	−0.0073 (14)	0.0094 (14)	−0.0012 (17)
C38	0.0213 (16)	0.0108 (19)	0.0128 (15)	−0.0023 (13)	0.0025 (13)	−0.0030 (15)
C39	0.0263 (17)	0.0144 (19)	0.0159 (16)	0.0024 (14)	0.0052 (13)	0.0004 (14)
C40	0.0182 (15)	0.0108 (17)	0.0175 (15)	0.0033 (12)	0.0024 (12)	0.0054 (13)
C41	0.0217 (17)	0.0117 (19)	0.0149 (16)	−0.0029 (14)	0.0037 (13)	−0.0036 (15)
C42	0.0247 (17)	0.022 (2)	0.0142 (16)	0.0045 (16)	0.0066 (13)	0.0028 (16)
C43	0.0229 (16)	0.0114 (18)	0.0186 (16)	0.0001 (13)	0.0106 (13)	−0.0006 (14)
C44	0.0315 (19)	0.0172 (19)	0.0217 (18)	−0.0032 (15)	0.0093 (14)	−0.0007 (15)
C45	0.0187 (15)	0.0137 (17)	0.0227 (17)	−0.0016 (13)	0.0020 (13)	0.0007 (15)
C46	0.0191 (16)	0.025 (2)	0.0261 (18)	0.0010 (14)	0.0009 (13)	0.0106 (16)
C47	0.0257 (18)	0.016 (2)	0.0128 (16)	−0.0072 (15)	0.0028 (13)	−0.0046 (15)
C48	0.0212 (17)	0.0134 (19)	0.0127 (15)	−0.0066 (14)	0.0040 (13)	0.0030 (15)
C49	0.033 (2)	0.022 (2)	0.030 (2)	−0.0011 (16)	0.0064 (16)	−0.0055 (18)
C50	0.040 (2)	0.017 (2)	0.0256 (19)	−0.0051 (16)	−0.0012 (15)	−0.0021 (16)
C51	0.0218 (17)	0.0135 (19)	0.0108 (15)	0.0024 (14)	0.0056 (13)	0.0018 (15)
C52	0.0174 (16)	0.0128 (19)	0.0217 (18)	0.0015 (14)	0.0074 (13)	0.0001 (16)
C53	0.035 (2)	0.0065 (18)	0.0276 (19)	−0.0026 (14)	0.0204 (16)	0.0020 (15)
C54	0.0323 (19)	0.025 (2)	0.028 (2)	0.0005 (16)	−0.0039 (16)	−0.0089 (18)
C55	0.040 (2)	0.021 (2)	0.041 (2)	0.0060 (17)	0.0215 (18)	0.0063 (19)
C56	0.047 (2)	0.022 (2)	0.0268 (19)	−0.0158 (17)	0.0157 (17)	−0.0091 (17)

Geometric parameters (Å, º)

O1—C42	1.322 (4)	C23—H23	0.9300
O1—H1C	0.8200	C24—H24	0.9300
O2—C42	1.204 (4)	C25—C26	1.386 (6)
O3—C37	1.217 (4)	C25—C29	1.400 (6)
O4—C37	1.305 (4)	C25—H25	0.9300
O4—H4C	0.8200	C26—H26	0.9300
O5—C47	1.206 (4)	C27—C28	1.383 (5)
O6—C47	1.324 (4)	C27—H27	0.9300
O6—H6C	0.8200	C28—C29	1.389 (6)
O7—C52	1.336 (4)	C28—H28	0.9300
O7—H7C	0.8200	C29—C30	1.461 (5)
O8—C52	1.204 (4)	C30—H30	0.9300
N1—C2	1.326 (6)	C31—C32	1.468 (5)
N1—C3	1.337 (5)	C31—H31	0.9300
N2—C6	1.268 (5)	C32—C33	1.389 (6)
N2—N3	1.406 (5)	C32—C36	1.392 (5)
N3—C7	1.274 (5)	C33—C34	1.381 (5)
N4—C10	1.320 (5)	C33—H33	0.9300
N4—C11	1.345 (5)	C34—H34	0.9300
N5—C15	1.336 (5)	C35—C36	1.380 (5)
N5—C14	1.343 (5)	C35—H35	0.9300
N6—C18	1.283 (5)	C36—H36	0.9300
N6—N7	1.419 (3)	C37—C38	1.542 (5)
N7—C19	1.270 (5)	C38—C44	1.519 (5)
N8—C22	1.315 (5)	C38—C39	1.548 (5)
N8—C23	1.345 (5)	C38—C43	1.578 (5)
N9—C26	1.322 (6)	C39—C40	1.546 (4)
N9—C27	1.331 (6)	C39—H39A	0.9700
N10—C30	1.283 (5)	C39—H39B	0.9700
N10—N11	1.413 (4)	C40—C41	1.534 (5)
N11—C31	1.265 (5)	C40—H40A	0.9700
N12—C34	1.331 (5)	C40—H40B	0.9700
N12—C35	1.348 (5)	C41—C42	1.516 (5)
C1—C2	1.389 (6)	C41—C43	1.574 (4)
C1—C5	1.388 (6)	C41—H41	0.9800
C1—H1	0.9300	C43—C46	1.518 (5)
C2—H2	0.9300	C43—C45	1.527 (5)
C3—C4	1.374 (6)	C44—H44A	0.9600
C3—H3	0.9300	C44—H44B	0.9600
C4—C5	1.403 (6)	C44—H44C	0.9600
C4—H4	0.9300	C45—H45A	0.9600
C5—C6	1.469 (6)	C45—H45B	0.9600
C6—H6	0.9300	C45—H45C	0.9600
C7—C8	1.470 (5)	C46—H46A	0.9600
C7—H7	0.9300	C46—H46B	0.9600
C8—C12	1.372 (5)	C46—H46C	0.9600
C8—C9	1.397 (6)	C47—C48	1.509 (5)
C9—C10	1.380 (5)	C48—C54	1.536 (5)
C9—H9	0.9300	C48—C49	1.546 (5)
C10—H10	0.9300	C48—C53	1.571 (5)
C11—C12	1.369 (6)	C49—C50	1.582 (5)
C11—H11	0.9300	C49—H49A	0.9700
C12—H12	0.9300	C49—H49B	0.9700
C13—C14	1.372 (5)	C50—C51	1.525 (5)
C13—C17	1.384 (5)	C50—H50A	0.9700
C13—H13	0.9300	C50—H50B	0.9700
C14—H14	0.9300	C51—C52	1.522 (5)
C15—C16	1.384 (5)	C51—C53	1.543 (4)
C15—H15	0.9300	C51—H51	0.9800
C16—C17	1.390 (5)	C53—C55	1.496 (5)
C16—H16	0.9300	C53—C56	1.546 (5)
C17—C18	1.472 (4)	C54—H54A	0.9600
C18—H18	0.9300	C54—H54B	0.9600
C19—C20	1.473 (5)	C54—H54C	0.9600
C19—H19	0.9300	C55—H55A	0.9600
C20—C24	1.384 (5)	C55—H55B	0.9600
C20—C21	1.393 (5)	C55—H55C	0.9600
C21—C22	1.396 (5)	C56—H56A	0.9600
C21—H21	0.9300	C56—H56B	0.9600
C22—H22	0.9300	C56—H56C	0.9600
C23—C24	1.389 (5)
C42—O1—H1C	109.5	N12—C34—H34	118.1
C37—O4—H4C	109.5	C33—C34—H34	118.1
C47—O6—H6C	109.5	N12—C35—C36	123.1 (4)
C52—O7—H7C	109.5	N12—C35—H35	118.5
C2—N1—C3	115.8 (4)	C36—C35—H35	118.5
C6—N2—N3	113.2 (3)	C35—C36—C32	118.8 (4)
C7—N3—N2	110.7 (3)	C35—C36—H36	120.6
C10—N4—C11	117.6 (3)	C32—C36—H36	120.6
C15—N5—C14	117.4 (3)	O3—C37—O4	124.4 (3)
C18—N6—N7	111.1 (3)	O3—C37—C38	123.3 (3)
C19—N7—N6	110.7 (3)	O4—C37—C38	112.3 (3)
C22—N8—C23	117.6 (3)	C44—C38—C37	108.7 (3)
C26—N9—C27	116.8 (4)	C44—C38—C39	110.2 (3)
C30—N10—N11	111.8 (3)	C37—C38—C39	113.0 (3)
C31—N11—N10	110.5 (3)	C44—C38—C43	112.3 (3)
C34—N12—C35	117.3 (3)	C37—C38—C43	109.4 (3)
C2—C1—C5	118.1 (4)	C39—C38—C43	103.1 (3)
C2—C1—H1	120.9	C40—C39—C38	106.5 (3)
C5—C1—H1	120.9	C40—C39—H39A	110.4
N1—C2—C1	125.3 (4)	C38—C39—H39A	110.4
N1—C2—H2	117.3	C40—C39—H39B	110.4
C1—C2—H2	117.3	C38—C39—H39B	110.4
N1—C3—C4	124.3 (4)	H39A—C39—H39B	108.6
N1—C3—H3	117.9	C41—C40—C39	105.4 (2)
C4—C3—H3	117.9	C41—C40—H40A	110.7
C3—C4—C5	119.2 (4)	C39—C40—H40A	110.7
C3—C4—H4	120.4	C41—C40—H40B	110.7
C5—C4—H4	120.4	C39—C40—H40B	110.7
C1—C5—C4	117.3 (4)	H40A—C40—H40B	108.8
C1—C5—C6	121.7 (4)	C42—C41—C40	118.1 (3)
C4—C5—C6	121.0 (4)	C42—C41—C43	113.1 (3)
N2—C6—C5	120.2 (4)	C40—C41—C43	104.4 (3)
N2—C6—H6	119.9	C42—C41—H41	106.9
C5—C6—H6	119.9	C40—C41—H41	106.9
N3—C7—C8	121.5 (4)	C43—C41—H41	106.9
N3—C7—H7	119.2	O2—C42—O1	122.7 (4)
C8—C7—H7	119.2	O2—C42—C41	122.6 (3)
C12—C8—C9	117.5 (4)	O1—C42—C41	114.7 (3)
C12—C8—C7	123.9 (4)	C46—C43—C45	108.3 (3)
C9—C8—C7	118.6 (4)	C46—C43—C41	112.6 (3)
C10—C9—C8	119.2 (3)	C45—C43—C41	110.7 (3)
C10—C9—H9	120.4	C46—C43—C38	115.0 (3)
C8—C9—H9	120.4	C45—C43—C38	111.1 (3)
N4—C10—C9	123.0 (4)	C41—C43—C38	98.8 (3)
N4—C10—H10	118.5	C38—C44—H44A	109.5
C9—C10—H10	118.5	C38—C44—H44B	109.5
N4—C11—C12	123.1 (4)	H44A—C44—H44B	109.5
N4—C11—H11	118.4	C38—C44—H44C	109.5
C12—C11—H11	118.4	H44A—C44—H44C	109.5
C11—C12—C8	119.6 (4)	H44B—C44—H44C	109.5
C11—C12—H12	120.2	C43—C45—H45A	109.5
C8—C12—H12	120.2	C43—C45—H45B	109.5
C14—C13—C17	119.6 (3)	H45A—C45—H45B	109.5
C14—C13—H13	120.2	C43—C45—H45C	109.5
C17—C13—H13	120.2	H45A—C45—H45C	109.5
N5—C14—C13	123.0 (3)	H45B—C45—H45C	109.5
N5—C14—H14	118.5	C43—C46—H46A	109.5
C13—C14—H14	118.5	C43—C46—H46B	109.5
N5—C15—C16	123.3 (3)	H46A—C46—H46B	109.5
N5—C15—H15	118.3	C43—C46—H46C	109.5
C16—C15—H15	118.3	H46A—C46—H46C	109.5
C15—C16—C17	118.7 (3)	H46B—C46—H46C	109.5
C15—C16—H16	120.6	O5—C47—O6	122.5 (3)
C17—C16—H16	120.6	O5—C47—C48	122.8 (3)
C13—C17—C16	118.0 (3)	O6—C47—C48	114.7 (3)
C13—C17—C18	118.8 (3)	C47—C48—C54	107.2 (3)
C16—C17—C18	123.2 (3)	C47—C48—C49	118.4 (3)
N6—C18—C17	121.3 (3)	C54—C48—C49	107.7 (3)
N6—C18—H18	119.3	C47—C48—C53	110.1 (3)
C17—C18—H18	119.3	C54—C48—C53	111.8 (3)
N7—C19—C20	122.0 (3)	C49—C48—C53	101.5 (3)
N7—C19—H19	119.0	C48—C49—C50	106.1 (3)
C20—C19—H19	119.0	C48—C49—H49A	110.5
C24—C20—C21	118.3 (3)	C50—C49—H49A	110.5
C24—C20—C19	124.0 (3)	C48—C49—H49B	110.5
C21—C20—C19	117.7 (3)	C50—C49—H49B	110.5
C20—C21—C22	118.2 (3)	H49A—C49—H49B	108.7
C20—C21—H21	120.9	C51—C50—C49	104.1 (3)
C22—C21—H21	120.9	C51—C50—H50A	110.9
N8—C22—C21	124.0 (3)	C49—C50—H50A	110.9
N8—C22—H22	118.0	C51—C50—H50B	110.9
C21—C22—H22	118.0	C49—C50—H50B	110.9
N8—C23—C24	122.8 (3)	H50A—C50—H50B	109.0
N8—C23—H23	118.6	C52—C51—C50	115.0 (3)
C24—C23—H23	118.6	C52—C51—C53	114.0 (3)
C20—C24—C23	119.1 (3)	C50—C51—C53	105.8 (3)
C20—C24—H24	120.4	C52—C51—H51	107.2
C23—C24—H24	120.4	C50—C51—H51	107.2
C26—C25—C29	118.8 (4)	C53—C51—H51	107.2
C26—C25—H25	120.6	O8—C52—O7	123.9 (3)
C29—C25—H25	120.6	O8—C52—C51	124.5 (3)
N9—C26—C25	124.0 (4)	O7—C52—C51	111.7 (3)
N9—C26—H26	118.0	C55—C53—C51	111.4 (3)
C25—C26—H26	118.0	C55—C53—C56	108.6 (3)
N9—C27—C28	124.3 (4)	C51—C53—C56	112.4 (3)
N9—C27—H27	117.9	C55—C53—C48	112.0 (3)
C28—C27—H27	117.9	C51—C53—C48	100.0 (3)
C27—C28—C29	118.8 (4)	C56—C53—C48	112.3 (3)
C27—C28—H28	120.6	C48—C54—H54A	109.5
C29—C28—H28	120.6	C48—C54—H54B	109.5
C28—C29—C25	117.3 (4)	H54A—C54—H54B	109.5
C28—C29—C30	122.3 (4)	C48—C54—H54C	109.5
C25—C29—C30	120.3 (4)	H54A—C54—H54C	109.5
N10—C30—C29	118.9 (3)	H54B—C54—H54C	109.5
N10—C30—H30	120.6	C53—C55—H55A	109.5
C29—C30—H30	120.6	C53—C55—H55B	109.5
N11—C31—C32	121.5 (4)	H55A—C55—H55B	109.5
N11—C31—H31	119.2	C53—C55—H55C	109.5
C32—C31—H31	119.2	H55A—C55—H55C	109.5
C33—C32—C36	118.4 (3)	H55B—C55—H55C	109.5
C33—C32—C31	120.4 (3)	C53—C56—H56A	109.5
C36—C32—C31	121.2 (4)	C53—C56—H56B	109.5
C34—C33—C32	118.6 (3)	H56A—C56—H56B	109.5
C34—C33—H33	120.7	C53—C56—H56C	109.5
C32—C33—H33	120.7	H56A—C56—H56C	109.5
N12—C34—C33	123.7 (4)	H56B—C56—H56C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···N5^i	0.82	1.88	2.694 (4)	176
O4—H4C···N4	0.82	1.83	2.639 (4)	171
O6—H6C···N12^ii	0.82	1.83	2.641 (4)	169
O7—H7C···N8^iii	0.82	1.89	2.702 (4)	172

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

(ccr32)

Crystal data

3(C12H10N4)·2(C10H16O4)	F(000) = 1092
Mr = 1031.18	Dx = 1.320 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4215 reflections
a = 9.9407 (10) Å	θ = 2.4–28.2°
b = 12.9624 (13) Å	µ = 0.09 mm^−1
c = 20.247 (2) Å	T = 150 K
β = 95.928 (2)°	Plate, yellow
V = 2595.0 (4) Å^3	0.23 × 0.11 × 0.04 mm
Z = 2

Data collection

Bruker SMART APEX CCD diffractometer	4541 independent reflections
Radiation source: fine-focus sealed tube	3787 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω and φ scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan SADABS (Bruker, 2008)	h = −11→9
Tmin = 0.979, Tmax = 0.996	k = −15→13
12644 measured reflections	l = −20→24

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0459P)^2 + 0.8495P] where P = (Fo^2 + 2Fc^2)/3
4541 reflections	(Δ/σ)max < 0.001
412 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	−0.08958 (13)	0.95695 (12)	0.30786 (7)	0.0430 (4)
H1C	−0.145 (3)	0.927 (2)	0.3421 (14)	0.081 (8)*
O2	0.06248 (14)	0.96506 (12)	0.39631 (6)	0.0461 (4)
O3	0.48108 (13)	0.85649 (11)	0.21087 (7)	0.0390 (3)
H3C	0.537 (3)	0.816 (2)	0.1830 (13)	0.074 (8)*
O4	0.34053 (14)	0.87419 (12)	0.11849 (7)	0.0486 (4)
C13	0.03267 (18)	0.97642 (14)	0.33711 (9)	0.0306 (4)
C18	0.37294 (18)	0.89556 (14)	0.17641 (9)	0.0303 (4)
C14	0.13302 (17)	1.01288 (13)	0.29066 (8)	0.0256 (4)	0.641 (3)
C15	0.0824 (5)	1.0627 (4)	0.2244 (2)	0.0340 (10)	0.641 (3)
H15A	0.0709	1.1379	0.2300	0.041*	0.641 (3)
H15B	−0.0058	1.0327	0.2069	0.041*	0.641 (3)
C16	0.1914 (3)	1.0406 (2)	0.17567 (13)	0.0297 (7)	0.641 (3)
H16A	0.1506	1.0052	0.1351	0.036*	0.641 (3)
H16B	0.2342	1.1055	0.1627	0.036*	0.641 (3)
C17	0.29606 (17)	0.97009 (13)	0.21587 (8)	0.0259 (4)	0.641 (3)
H17	0.3647	1.0167	0.2400	0.031*	0.641 (3)
C19	0.2182 (5)	0.9192 (5)	0.2687 (3)	0.0262 (11)	0.641 (3)
C20	0.2259 (5)	1.0915 (3)	0.3320 (2)	0.0344 (10)	0.641 (3)
H20A	0.1719	1.1508	0.3436	0.052*	0.641 (3)
H20B	0.2974	1.1150	0.3056	0.052*	0.641 (3)
H20C	0.2667	1.0582	0.3727	0.052*	0.641 (3)
C21	0.1232 (3)	0.8348 (2)	0.23736 (18)	0.0368 (8)	0.641 (3)
H21A	0.0578	0.8657	0.2035	0.055*	0.641 (3)
H21B	0.0749	0.8027	0.2718	0.055*	0.641 (3)
H21C	0.1763	0.7824	0.2168	0.055*	0.641 (3)
C22	0.3108 (4)	0.8700 (2)	0.32544 (15)	0.0371 (9)	0.641 (3)
H22A	0.2565	0.8479	0.3607	0.056*	0.641 (3)
H22B	0.3783	0.9205	0.3433	0.056*	0.641 (3)
H22C	0.3567	0.8101	0.3086	0.056*	0.641 (3)
C14A	0.13302 (17)	1.01288 (13)	0.29066 (8)	0.0256 (4)	0.359 (3)
C15A	0.2615 (9)	1.0605 (6)	0.3191 (4)	0.0293 (17)	0.359 (3)
H15C	0.2859	1.0349	0.3648	0.035*	0.359 (3)
H15D	0.2514	1.1364	0.3209	0.035*	0.359 (3)
C16A	0.3721 (5)	1.0320 (4)	0.2749 (2)	0.0272 (13)	0.359 (3)
H16C	0.4426	0.9889	0.2996	0.033*	0.359 (3)
H16D	0.4150	1.0946	0.2586	0.033*	0.359 (3)
C17A	0.29606 (17)	0.97009 (13)	0.21587 (8)	0.0259 (4)	0.359 (3)
H17A	0.2528	1.0219	0.1838	0.031*	0.359 (3)
C19A	0.1770 (9)	0.9146 (9)	0.2498 (5)	0.023 (2)	0.359 (3)
C20A	0.0546 (12)	1.0923 (8)	0.2435 (5)	0.051 (2)	0.359 (3)
H20D	0.0201	1.1479	0.2699	0.077*	0.359 (3)
H20E	−0.0211	1.0578	0.2176	0.077*	0.359 (3)
H20F	0.1157	1.1213	0.2133	0.077*	0.359 (3)
C21A	0.0722 (5)	0.8724 (5)	0.1967 (3)	0.0352 (14)	0.359 (3)
H21D	0.1111	0.8146	0.1739	0.053*	0.359 (3)
H21E	0.0449	0.9269	0.1646	0.053*	0.359 (3)
H21F	−0.0070	0.8485	0.2175	0.053*	0.359 (3)
C22A	0.2300 (5)	0.8308 (4)	0.2974 (3)	0.0272 (13)	0.359 (3)
H22D	0.1544	0.7990	0.3174	0.041*	0.359 (3)
H22E	0.2937	0.8607	0.3324	0.041*	0.359 (3)
H22F	0.2763	0.7782	0.2733	0.041*	0.359 (3)
N1	0.55714 (19)	1.13128 (14)	0.16838 (10)	0.0524 (5)
N2	0.86784 (17)	0.90730 (13)	0.04956 (8)	0.0417 (4)
N3	0.92698 (17)	0.85981 (13)	−0.00306 (8)	0.0416 (4)
N4	1.26097 (16)	0.63882 (13)	−0.11011 (8)	0.0391 (4)
C1	0.72220 (19)	1.00527 (15)	0.14525 (10)	0.0375 (5)
H1	0.7886	0.9566	0.1620	0.045*
C2	0.6521 (2)	1.06189 (16)	0.18776 (11)	0.0454 (5)
H2	0.6726	1.0508	0.2341	0.055*
C3	0.5301 (2)	1.14399 (17)	0.10304 (13)	0.0521 (6)
H3	0.4623	1.1925	0.0877	0.063*
C4	0.5944 (2)	1.09107 (16)	0.05624 (11)	0.0438 (5)
H4	0.5705	1.1029	0.0102	0.053*
C5	0.69429 (18)	1.02052 (14)	0.07732 (10)	0.0357 (5)
C6	0.7686 (2)	0.96519 (15)	0.02916 (10)	0.0386 (5)
H6	0.7427	0.9726	−0.0171	0.046*
C7	1.03603 (19)	0.81378 (15)	0.01796 (10)	0.0365 (5)
H7	1.0676	0.8170	0.0638	0.044*
C8	1.11376 (18)	0.75588 (14)	−0.02731 (9)	0.0313 (4)
C9	1.0808 (2)	0.75541 (17)	−0.09512 (9)	0.0409 (5)
H9	1.0070	0.7953	−0.1146	0.049*
C10	1.1560 (2)	0.69647 (18)	−0.13417 (10)	0.0461 (5)
H10	1.1319	0.6968	−0.1808	0.055*
C11	1.29345 (19)	0.64035 (15)	−0.04475 (10)	0.0382 (5)
H11	1.3686	0.6004	−0.0267	0.046*
C12	1.22359 (18)	0.69691 (15)	−0.00190 (10)	0.0358 (5)
H12	1.2503	0.6956	0.0445	0.043*
N5	0.64034 (15)	0.74245 (11)	0.14003 (7)	0.0312 (4)
N6	0.97686 (15)	0.52846 (11)	0.02657 (7)	0.0299 (3)
C23	0.84243 (18)	0.65255 (14)	0.12027 (9)	0.0309 (4)
H23	0.9311	0.6309	0.1364	0.037*
C24	0.76608 (18)	0.71014 (14)	0.15968 (9)	0.0327 (4)
H24	0.8046	0.7279	0.2031	0.039*
C25	0.58888 (18)	0.71799 (15)	0.07868 (9)	0.0344 (4)
H25	0.5001	0.7409	0.0639	0.041*
C26	0.65784 (18)	0.66117 (14)	0.03571 (9)	0.0332 (4)
H26	0.6172	0.6457	−0.0077	0.040*
C27	0.78775 (17)	0.62668 (13)	0.05656 (8)	0.0267 (4)
C28	0.85970 (17)	0.56555 (14)	0.01009 (9)	0.0286 (4)
H28	0.8175	0.5534	−0.0335	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0310 (8)	0.0558 (9)	0.0439 (8)	−0.0009 (6)	0.0112 (6)	0.0082 (7)
O2	0.0477 (9)	0.0635 (10)	0.0291 (8)	0.0068 (7)	0.0139 (6)	0.0108 (7)
O3	0.0385 (8)	0.0440 (8)	0.0364 (8)	0.0127 (6)	0.0131 (6)	−0.0018 (6)
O4	0.0479 (9)	0.0612 (10)	0.0376 (8)	0.0080 (7)	0.0085 (7)	−0.0192 (7)
C13	0.0333 (10)	0.0292 (10)	0.0307 (10)	0.0090 (8)	0.0096 (8)	0.0017 (8)
C18	0.0329 (10)	0.0286 (10)	0.0311 (10)	−0.0026 (8)	0.0119 (8)	−0.0023 (8)
C14	0.0300 (9)	0.0249 (9)	0.0224 (9)	0.0046 (7)	0.0058 (7)	0.0015 (7)
C15	0.033 (2)	0.035 (3)	0.034 (3)	0.0014 (18)	0.0024 (18)	0.0051 (18)
C16	0.0342 (16)	0.0261 (15)	0.0284 (15)	0.0032 (12)	0.0009 (12)	0.0054 (12)
C17	0.0290 (9)	0.0252 (9)	0.0244 (9)	−0.0002 (7)	0.0063 (7)	−0.0010 (7)
C19	0.027 (3)	0.021 (2)	0.032 (3)	−0.004 (2)	0.0073 (19)	−0.005 (2)
C20	0.044 (3)	0.030 (3)	0.030 (2)	0.0030 (17)	0.0086 (18)	−0.0053 (18)
C21	0.0427 (19)	0.0276 (17)	0.043 (2)	−0.0058 (15)	0.0173 (17)	−0.0045 (15)
C22	0.046 (2)	0.0344 (17)	0.0329 (17)	0.0167 (15)	0.0121 (15)	0.0056 (14)
C14A	0.0300 (9)	0.0249 (9)	0.0224 (9)	0.0046 (7)	0.0058 (7)	0.0015 (7)
C15A	0.045 (5)	0.024 (4)	0.021 (3)	−0.006 (3)	0.012 (3)	−0.008 (3)
C16A	0.027 (3)	0.028 (3)	0.027 (3)	−0.008 (2)	0.006 (2)	−0.007 (2)
C17A	0.0290 (9)	0.0252 (9)	0.0244 (9)	−0.0002 (7)	0.0063 (7)	−0.0010 (7)
C19A	0.019 (5)	0.025 (4)	0.026 (5)	−0.007 (4)	0.005 (3)	−0.007 (4)
C20A	0.055 (6)	0.048 (6)	0.054 (6)	0.000 (4)	0.019 (4)	0.008 (4)
C21A	0.029 (3)	0.042 (3)	0.033 (3)	0.002 (2)	−0.005 (2)	−0.013 (3)
C22A	0.028 (3)	0.021 (3)	0.033 (3)	0.002 (2)	0.005 (2)	0.000 (2)
N1	0.0542 (12)	0.0386 (10)	0.0670 (14)	0.0029 (9)	0.0189 (10)	−0.0085 (9)
N2	0.0453 (10)	0.0389 (10)	0.0436 (10)	0.0028 (8)	0.0171 (8)	−0.0011 (8)
N3	0.0437 (10)	0.0424 (10)	0.0410 (10)	0.0040 (8)	0.0160 (8)	−0.0002 (8)
N4	0.0310 (9)	0.0449 (10)	0.0428 (10)	−0.0070 (7)	0.0110 (7)	−0.0076 (8)
C1	0.0331 (10)	0.0315 (10)	0.0485 (12)	−0.0037 (8)	0.0072 (9)	−0.0023 (9)
C2	0.0478 (13)	0.0380 (12)	0.0519 (13)	−0.0025 (10)	0.0115 (10)	−0.0072 (10)
C3	0.0450 (13)	0.0367 (12)	0.0760 (17)	0.0091 (10)	0.0127 (12)	0.0019 (11)
C4	0.0423 (12)	0.0363 (11)	0.0531 (13)	−0.0022 (9)	0.0066 (10)	0.0006 (10)
C5	0.0304 (10)	0.0279 (10)	0.0502 (12)	−0.0070 (8)	0.0103 (9)	−0.0032 (9)
C6	0.0383 (11)	0.0360 (11)	0.0426 (11)	−0.0064 (9)	0.0097 (9)	−0.0012 (9)
C7	0.0395 (11)	0.0361 (11)	0.0352 (10)	−0.0050 (9)	0.0106 (9)	−0.0012 (8)
C8	0.0290 (9)	0.0294 (10)	0.0366 (10)	−0.0087 (8)	0.0090 (8)	−0.0012 (8)
C9	0.0380 (11)	0.0514 (13)	0.0335 (11)	0.0067 (9)	0.0040 (9)	0.0012 (9)
C10	0.0415 (12)	0.0656 (15)	0.0313 (11)	0.0019 (11)	0.0046 (9)	−0.0074 (10)
C11	0.0271 (10)	0.0372 (11)	0.0510 (13)	−0.0049 (8)	0.0072 (9)	0.0018 (9)
C12	0.0326 (10)	0.0424 (11)	0.0329 (10)	−0.0071 (9)	0.0054 (8)	0.0004 (9)
N5	0.0327 (8)	0.0291 (8)	0.0337 (8)	0.0026 (6)	0.0119 (7)	0.0003 (7)
N6	0.0294 (8)	0.0306 (8)	0.0314 (8)	−0.0005 (6)	0.0111 (6)	−0.0061 (6)
C23	0.0288 (10)	0.0328 (10)	0.0315 (10)	0.0055 (8)	0.0047 (8)	0.0025 (8)
C24	0.0357 (10)	0.0346 (10)	0.0282 (10)	0.0032 (8)	0.0053 (8)	−0.0018 (8)
C25	0.0263 (9)	0.0369 (11)	0.0403 (11)	0.0055 (8)	0.0051 (8)	−0.0031 (9)
C26	0.0295 (10)	0.0371 (11)	0.0329 (10)	0.0022 (8)	0.0028 (8)	−0.0049 (8)
C27	0.0286 (9)	0.0236 (9)	0.0293 (9)	−0.0008 (7)	0.0089 (7)	0.0000 (7)
C28	0.0273 (10)	0.0311 (10)	0.0280 (9)	0.0006 (8)	0.0055 (7)	−0.0018 (8)

Geometric parameters (Å, º)

O1—C13	1.320 (2)	C22A—H22E	0.9800
O1—H1C	1.01 (3)	C22A—H22F	0.9800
O2—C13	1.214 (2)	N1—C3	1.333 (3)
O3—C18	1.320 (2)	N1—C2	1.333 (3)
O3—H3C	0.98 (3)	N2—C6	1.274 (2)
O4—C18	1.216 (2)	N2—N3	1.410 (2)
C13—C14	1.516 (2)	N3—C7	1.272 (2)
C18—C17	1.510 (2)	N4—C11	1.330 (3)
C14—C15	1.526 (5)	N4—C10	1.334 (3)
C14—C20	1.560 (5)	C1—C2	1.375 (3)
C14—C19	1.571 (7)	C1—C5	1.389 (3)
C15—C16	1.566 (5)	C1—H1	0.9500
C15—H15A	0.9900	C2—H2	0.9500
C15—H15B	0.9900	C3—C4	1.379 (3)
C16—C17	1.551 (3)	C3—H3	0.9500
C16—H16A	0.9900	C4—C5	1.385 (3)
C16—H16B	0.9900	C4—H4	0.9500
C17—C19	1.533 (7)	C5—C6	1.469 (3)
C17—H17	1.0000	C6—H6	0.9500
C19—C22	1.535 (6)	C7—C8	1.465 (3)
C19—C21	1.538 (5)	C7—H7	0.9500
C20—H20A	0.9800	C8—C9	1.378 (3)
C20—H20B	0.9800	C8—C12	1.387 (3)
C20—H20C	0.9800	C9—C10	1.375 (3)
C21—H21A	0.9800	C9—H9	0.9500
C21—H21B	0.9800	C10—H10	0.9500
C21—H21C	0.9800	C11—C12	1.377 (3)
C22—H22A	0.9800	C11—H11	0.9500
C22—H22B	0.9800	C12—H12	0.9500
C22—H22C	0.9800	N5—C25	1.332 (2)
C15A—C16A	1.532 (8)	N5—C24	1.339 (2)
C15A—H15C	0.9900	N6—C28	1.272 (2)
C15A—H15D	0.9900	N6—N6^i	1.420 (3)
C16A—H16C	0.9900	C23—C24	1.377 (2)
C16A—H16D	0.9900	C23—C27	1.388 (2)
C19A—C22A	1.510 (12)	C23—H23	0.9500
C19A—C21A	1.519 (8)	C24—H24	0.9500
C20A—H20D	0.9800	C25—C26	1.376 (3)
C20A—H20E	0.9800	C25—H25	0.9500
C20A—H20F	0.9800	C26—C27	1.390 (2)
C21A—H21D	0.9800	C26—H26	0.9500
C21A—H21E	0.9800	C27—C28	1.471 (2)
C21A—H21F	0.9800	C28—H28	0.9500
C22A—H22D	0.9800
C13—O1—H1C	108.1 (15)	C3—N1—C2	116.09 (19)
C18—O3—H3C	112.3 (15)	C6—N2—N3	112.42 (17)
O2—C13—O1	122.64 (17)	C7—N3—N2	111.06 (17)
O2—C13—C14	122.79 (17)	C11—N4—C10	117.10 (17)
O1—C13—C14	114.56 (15)	C2—C1—C5	118.80 (19)
O4—C18—O3	122.85 (17)	C2—C1—H1	120.6
O4—C18—C17	123.90 (17)	C5—C1—H1	120.6
O3—C18—C17	113.24 (15)	N1—C2—C1	124.4 (2)
C13—C14—C15	119.9 (2)	N1—C2—H2	117.8
C13—C14—C20	105.2 (2)	C1—C2—H2	117.8
C15—C14—C20	108.6 (3)	N1—C3—C4	124.1 (2)
C13—C14—C19	110.1 (3)	N1—C3—H3	118.0
C15—C14—C19	102.5 (3)	C4—C3—H3	118.0
C20—C14—C19	110.5 (3)	C3—C4—C5	119.0 (2)
C14—C15—C16	106.9 (3)	C3—C4—H4	120.5
C14—C15—H15A	110.4	C5—C4—H4	120.5
C16—C15—H15A	110.4	C4—C5—C1	117.57 (19)
C14—C15—H15B	110.4	C4—C5—C6	120.75 (19)
C16—C15—H15B	110.4	C1—C5—C6	121.67 (18)
H15A—C15—H15B	108.6	N2—C6—C5	119.85 (19)
C17—C16—C15	104.3 (2)	N2—C6—H6	120.1
C17—C16—H16A	110.9	C5—C6—H6	120.1
C15—C16—H16A	110.9	N3—C7—C8	121.15 (18)
C17—C16—H16B	110.9	N3—C7—H7	119.4
C15—C16—H16B	110.9	C8—C7—H7	119.4
H16A—C16—H16B	108.9	C9—C8—C12	117.65 (18)
C18—C17—C19	114.4 (3)	C9—C8—C7	122.62 (18)
C18—C17—C16	116.62 (16)	C12—C8—C7	119.72 (17)
C19—C17—C16	105.1 (2)	C10—C9—C8	119.20 (19)
C18—C17—H17	106.7	C10—C9—H9	120.4
C19—C17—H17	106.7	C8—C9—H9	120.4
C16—C17—H17	106.7	N4—C10—C9	123.55 (19)
C17—C19—C22	113.2 (4)	N4—C10—H10	118.2
C17—C19—C21	110.5 (4)	C9—C10—H10	118.2
C22—C19—C21	108.0 (5)	N4—C11—C12	123.27 (19)
C17—C19—C14	101.0 (4)	N4—C11—H11	118.4
C22—C19—C14	114.1 (4)	C12—C11—H11	118.4
C21—C19—C14	109.9 (3)	C11—C12—C8	119.23 (18)
C16A—C15A—H15C	110.0	C11—C12—H12	120.4
C16A—C15A—H15D	110.0	C8—C12—H12	120.4
H15C—C15A—H15D	108.4	C25—N5—C24	117.35 (15)
C15A—C16A—H16C	110.9	C28—N6—N6^i	110.92 (17)
C15A—C16A—H16D	110.9	C24—C23—C27	118.90 (16)
H16C—C16A—H16D	108.9	C24—C23—H23	120.6
C22A—C19A—C21A	111.2 (8)	C27—C23—H23	120.6
H20D—C20A—H20E	109.5	N5—C24—C23	123.43 (17)
H20D—C20A—H20F	109.5	N5—C24—H24	118.3
H20E—C20A—H20F	109.5	C23—C24—H24	118.3
C19A—C21A—H21D	109.5	N5—C25—C26	123.29 (17)
C19A—C21A—H21E	109.5	N5—C25—H25	118.4
H21D—C21A—H21E	109.5	C26—C25—H25	118.4
C19A—C21A—H21F	109.5	C25—C26—C27	119.21 (17)
H21D—C21A—H21F	109.5	C25—C26—H26	120.4
H21E—C21A—H21F	109.5	C27—C26—H26	120.4
C19A—C22A—H22D	109.5	C23—C27—C26	117.82 (16)
C19A—C22A—H22E	109.5	C23—C27—C28	123.70 (16)
H22D—C22A—H22E	109.5	C26—C27—C28	118.48 (16)
C19A—C22A—H22F	109.5	N6—C28—C27	121.89 (16)
H22D—C22A—H22F	109.5	N6—C28—H28	119.1
H22E—C22A—H22F	109.5	C27—C28—H28	119.1
O2—C13—C14—C15	−157.6 (3)	C5—C1—C2—N1	0.3 (3)
O1—C13—C14—C15	23.0 (3)	C2—N1—C3—C4	−0.6 (3)
O2—C13—C14—C20	−35.2 (3)	N1—C3—C4—C5	−0.5 (3)
O1—C13—C14—C20	145.5 (2)	C3—C4—C5—C1	1.4 (3)
O2—C13—C14—C19	83.9 (3)	C3—C4—C5—C6	−177.85 (18)
O1—C13—C14—C19	−95.4 (2)	C2—C1—C5—C4	−1.3 (3)
C13—C14—C15—C16	−152.0 (2)	C2—C1—C5—C6	177.92 (18)
C20—C14—C15—C16	87.2 (3)	N3—N2—C6—C5	179.67 (16)
C19—C14—C15—C16	−29.8 (4)	C4—C5—C6—N2	173.99 (18)
C14—C15—C16—C17	4.5 (4)	C1—C5—C6—N2	−5.2 (3)
O4—C18—C17—C19	108.7 (3)	N2—N3—C7—C8	178.08 (16)
O3—C18—C17—C19	−72.3 (3)	N3—C7—C8—C9	5.9 (3)
O4—C18—C17—C16	−14.5 (3)	N3—C7—C8—C12	−172.68 (18)
O3—C18—C17—C16	164.55 (17)	C12—C8—C9—C10	0.7 (3)
C15—C16—C17—C18	151.4 (3)	C7—C8—C9—C10	−177.89 (19)
C15—C16—C17—C19	23.5 (4)	C11—N4—C10—C9	−0.6 (3)
C18—C17—C19—C22	66.8 (4)	C8—C9—C10—N4	−0.2 (3)
C16—C17—C19—C22	−164.0 (3)	C10—N4—C11—C12	0.7 (3)
C18—C17—C19—C21	−54.5 (4)	N4—C11—C12—C8	−0.2 (3)
C16—C17—C19—C21	74.7 (4)	C9—C8—C12—C11	−0.6 (3)
C18—C17—C19—C14	−170.80 (19)	C7—C8—C12—C11	178.07 (17)
C16—C17—C19—C14	−41.6 (3)	C25—N5—C24—C23	−0.9 (3)
C13—C14—C19—C17	172.45 (18)	C27—C23—C24—N5	0.4 (3)
C15—C14—C19—C17	43.8 (3)	C24—N5—C25—C26	0.6 (3)
C20—C14—C19—C17	−71.8 (3)	N5—C25—C26—C27	0.2 (3)
C13—C14—C19—C22	−65.8 (4)	C24—C23—C27—C26	0.3 (3)
C15—C14—C19—C22	165.6 (4)	C24—C23—C27—C28	−179.98 (17)
C20—C14—C19—C22	50.0 (5)	C25—C26—C27—C23	−0.6 (3)
C13—C14—C19—C21	55.7 (4)	C25—C26—C27—C28	179.67 (17)
C15—C14—C19—C21	−73.0 (5)	N6^i—N6—C28—C27	179.13 (17)
C20—C14—C19—C21	171.5 (3)	C23—C27—C28—N6	2.8 (3)
C6—N2—N3—C7	171.31 (17)	C26—C27—C28—N6	−177.52 (17)
C3—N1—C2—C1	0.6 (3)

Symmetry code: (i) −x+2, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···N4^ii	1.01 (3)	1.65 (3)	2.649 (2)	170 (2)
O3—H3C···N5	0.98 (3)	1.71 (3)	2.6866 (19)	176 (2)

Symmetry code: (ii) x−3/2, −y+3/2, z+1/2.