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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520613031260/bi5004sup1.cif
Contains datablocks ccp11, ccp32, ccr32, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520613031260/bi5004ccp11sup2.hkl
Contains datablock ccp11

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520613031260/bi5004ccp32sup3.hkl
Contains datablock ccp32

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520613031260/bi5004ccr32sup4.hkl
Contains datablock ccr32

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520613031260/bi5004sup5.pdf
Synthesis, spectroscopic and thermal characterization

CCDC references: 947210; 947212; 947213

Computing details top

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 top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
(ccp11) top
Crystal data top
C12H10N4·C10H16O4F(000) = 872
Mr = 410.47Dx = 1.306 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5868 reflections
a = 7.2598 (11) Åθ = 2.5–28.2°
b = 10.2744 (15) ŵ = 0.09 mm1
c = 27.997 (4) ÅT = 150 K
V = 2088.3 (5) Å3Plate, yellow
Z = 40.23 × 0.11 × 0.09 mm
Data collection top
Bruker SMART APEX CCD
diffractometer
4834 independent reflections
Radiation source: fine-focus sealed tube4686 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
ω and φ scansθmax = 28.0°, θmin = 1.5°
Absorption correction: multi-scan
SADABS (Bruker, 2008)
h = 99
Tmin = 0.979, Tmax = 0.992k = 1213
12500 measured reflectionsl = 2136
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 1.13 w = 1/[σ2(Fo2) + (0.0482P)2 + 0.7672P]
where P = (Fo2 + 2Fc2)/3
4834 reflections(Δ/σ)max < 0.001
282 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C12H10N4·C10H16O4V = 2088.3 (5) Å3
Mr = 410.47Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.2598 (11) ŵ = 0.09 mm1
b = 10.2744 (15) ÅT = 150 K
c = 27.997 (4) Å0.23 × 0.11 × 0.09 mm
Data collection top
Bruker SMART APEX CCD
diffractometer
4834 independent reflections
Absorption correction: multi-scan
SADABS (Bruker, 2008)
4686 reflections with I > 2σ(I)
Tmin = 0.979, Tmax = 0.992Rint = 0.026
12500 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 1.13Δρmax = 0.34 e Å3
4834 reflectionsΔρmin = 0.25 e Å3
282 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
N10.0406 (2)0.88912 (16)0.13837 (6)0.0195 (3)
N20.6433 (2)0.87659 (16)0.22967 (6)0.0201 (3)
N30.8147 (2)0.92533 (16)0.24548 (6)0.0209 (4)
N41.4240 (2)0.95420 (16)0.32922 (6)0.0187 (3)
C10.2888 (3)0.81464 (18)0.18764 (6)0.0183 (4)
H10.33710.74930.20810.022*
C20.1182 (3)0.79962 (19)0.16671 (7)0.0198 (4)
H20.05220.72150.17270.024*
C30.1362 (3)0.99764 (19)0.12946 (7)0.0219 (4)
H30.08271.06190.10940.026*
C40.3101 (3)1.02048 (19)0.14820 (7)0.0212 (4)
H40.37431.09840.14070.025*
C50.3894 (3)0.92800 (18)0.17812 (7)0.0184 (4)
C60.5714 (3)0.95315 (19)0.19909 (7)0.0211 (4)
H60.63741.02870.18960.025*
C70.8892 (3)0.85399 (18)0.27737 (6)0.0177 (4)
H70.82730.77880.28890.021*
C81.0727 (3)0.88954 (18)0.29613 (6)0.0172 (4)
C91.1548 (3)1.00770 (18)0.28402 (7)0.0182 (4)
H91.09221.06790.26400.022*
C101.3282 (3)1.03615 (19)0.30142 (7)0.0202 (4)
H101.38211.11750.29330.024*
C111.3447 (3)0.84079 (19)0.34080 (7)0.0204 (4)
H111.41120.78210.36060.024*
C121.1707 (3)0.80469 (18)0.32546 (7)0.0194 (4)
H121.11910.72360.33480.023*
O10.2655 (2)0.52565 (13)0.12468 (5)0.0209 (3)
H1C0.353 (4)0.500 (2)0.1422 (9)0.033 (7)*
O20.2392 (2)0.31321 (13)0.10887 (5)0.0225 (3)
O30.2399 (2)0.63474 (13)0.08384 (5)0.0222 (3)
H3C0.324 (4)0.624 (3)0.1045 (10)0.047 (8)*
O40.2176 (2)0.41848 (13)0.09293 (5)0.0215 (3)
C130.2005 (3)0.42547 (18)0.09968 (6)0.0162 (4)
C140.0764 (2)0.46710 (17)0.05834 (6)0.0143 (3)
C150.0027 (3)0.34745 (18)0.03156 (7)0.0176 (4)
H15A0.10450.30960.04850.021*
H15B0.09930.28000.02850.021*
C160.0540 (3)0.39916 (19)0.01778 (7)0.0197 (4)
H16A0.18680.42110.01820.024*
H16B0.02960.33320.04280.024*
C170.0642 (2)0.52248 (17)0.02638 (6)0.0150 (3)
H170.02070.59890.02890.018*
C180.1792 (3)0.51700 (18)0.07144 (7)0.0164 (4)
C190.1896 (2)0.54201 (17)0.01911 (6)0.0147 (4)
C200.0848 (3)0.54934 (18)0.07751 (7)0.0181 (4)
H20A0.16070.49610.09890.027*
H20B0.16000.58010.05070.027*
H20C0.03620.62420.09520.027*
C210.3811 (3)0.47884 (19)0.01256 (7)0.0201 (4)
H21A0.45240.48820.04210.030*
H21B0.44630.52200.01370.030*
H21C0.36620.38620.00510.030*
C220.2186 (3)0.68729 (18)0.02948 (7)0.0196 (4)
H22A0.28370.72770.00260.029*
H22B0.29190.69720.05870.029*
H22C0.09880.72970.03380.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0190 (8)0.0239 (8)0.0155 (8)0.0023 (7)0.0020 (6)0.0007 (6)
N20.0175 (8)0.0242 (8)0.0188 (8)0.0001 (7)0.0012 (6)0.0028 (7)
N30.0171 (8)0.0250 (8)0.0205 (8)0.0005 (7)0.0023 (6)0.0008 (7)
N40.0156 (7)0.0244 (8)0.0160 (8)0.0005 (6)0.0006 (6)0.0034 (6)
C10.0217 (9)0.0172 (8)0.0160 (9)0.0036 (7)0.0003 (7)0.0004 (7)
C20.0200 (9)0.0193 (9)0.0202 (9)0.0018 (7)0.0009 (8)0.0033 (7)
C30.0212 (9)0.0238 (10)0.0205 (9)0.0049 (8)0.0017 (8)0.0028 (8)
C40.0212 (9)0.0194 (9)0.0229 (10)0.0016 (8)0.0008 (8)0.0028 (8)
C50.0185 (9)0.0218 (9)0.0149 (9)0.0019 (7)0.0001 (7)0.0036 (7)
C60.0204 (9)0.0227 (10)0.0201 (9)0.0021 (8)0.0001 (8)0.0001 (7)
C70.0187 (9)0.0188 (9)0.0155 (9)0.0013 (7)0.0009 (7)0.0025 (7)
C80.0171 (9)0.0216 (9)0.0129 (8)0.0030 (7)0.0009 (7)0.0045 (7)
C90.0200 (9)0.0184 (9)0.0162 (9)0.0020 (7)0.0015 (7)0.0015 (7)
C100.0227 (9)0.0191 (9)0.0188 (9)0.0024 (8)0.0032 (8)0.0001 (7)
C110.0200 (9)0.0225 (9)0.0188 (9)0.0060 (7)0.0015 (7)0.0007 (7)
C120.0211 (9)0.0174 (8)0.0197 (9)0.0002 (7)0.0010 (8)0.0006 (7)
O10.0223 (7)0.0198 (6)0.0206 (7)0.0028 (6)0.0074 (6)0.0005 (5)
O20.0262 (7)0.0179 (6)0.0234 (7)0.0011 (6)0.0060 (6)0.0048 (5)
O30.0257 (7)0.0197 (6)0.0213 (7)0.0006 (6)0.0086 (6)0.0019 (5)
O40.0230 (7)0.0215 (7)0.0200 (7)0.0013 (6)0.0027 (6)0.0045 (5)
C130.0147 (8)0.0188 (8)0.0151 (9)0.0005 (7)0.0029 (7)0.0001 (7)
C140.0149 (8)0.0133 (8)0.0148 (8)0.0003 (7)0.0009 (7)0.0007 (6)
C150.0194 (9)0.0152 (8)0.0181 (9)0.0031 (7)0.0006 (7)0.0004 (7)
C160.0184 (9)0.0226 (9)0.0180 (9)0.0072 (7)0.0008 (7)0.0005 (7)
C170.0130 (8)0.0161 (8)0.0158 (8)0.0005 (7)0.0016 (7)0.0001 (7)
C180.0141 (8)0.0207 (9)0.0145 (8)0.0005 (7)0.0010 (7)0.0024 (7)
C190.0129 (8)0.0155 (8)0.0157 (9)0.0010 (7)0.0014 (7)0.0003 (7)
C200.0184 (9)0.0193 (9)0.0168 (9)0.0038 (7)0.0031 (8)0.0015 (7)
C210.0131 (8)0.0262 (9)0.0209 (9)0.0028 (7)0.0005 (7)0.0003 (8)
C220.0220 (10)0.0172 (8)0.0195 (9)0.0037 (8)0.0006 (8)0.0000 (7)
Geometric parameters (Å, º) top
N1—C31.337 (3)O2—C131.215 (2)
N1—C21.339 (3)O3—C181.333 (2)
N2—C61.274 (3)O3—H3C0.85 (3)
N2—N31.413 (2)O4—C181.210 (2)
N3—C71.275 (3)C13—C141.528 (2)
N4—C111.340 (3)C14—C151.536 (2)
N4—C101.341 (3)C14—C201.540 (2)
C1—C21.379 (3)C14—C191.573 (2)
C1—C51.401 (3)C15—C161.536 (3)
C1—H10.9500C15—H15A0.9900
C2—H20.9500C15—H15B0.9900
C3—C41.387 (3)C16—C171.549 (2)
C3—H30.9500C16—H16A0.9900
C4—C51.391 (3)C16—H16B0.9900
C4—H40.9500C17—C181.514 (2)
C5—C61.469 (3)C17—C191.578 (3)
C6—H60.9500C17—H171.0000
C7—C81.478 (3)C19—C221.535 (2)
C7—H70.9500C19—C211.546 (3)
C8—C121.393 (3)C20—H20A0.9800
C8—C91.394 (3)C20—H20B0.9800
C9—C101.381 (3)C20—H20C0.9800
C9—H90.9500C21—H21A0.9800
C10—H100.9500C21—H21B0.9800
C11—C121.385 (3)C21—H21C0.9800
C11—H110.9500C22—H22A0.9800
C12—H120.9500C22—H22B0.9800
O1—C131.331 (2)C22—H22C0.9800
O1—H1C0.85 (3)
C3—N1—C2117.69 (17)C13—C14—C19110.96 (14)
C6—N2—N3110.64 (16)C15—C14—C19103.47 (14)
C7—N3—N2112.89 (16)C20—C14—C19111.83 (14)
C11—N4—C10117.62 (17)C14—C15—C16104.80 (14)
C2—C1—C5118.74 (18)C14—C15—H15A110.8
C2—C1—H1120.6C16—C15—H15A110.8
C5—C1—H1120.6C14—C15—H15B110.8
N1—C2—C1123.59 (18)C16—C15—H15B110.8
N1—C2—H2118.2H15A—C15—H15B108.9
C1—C2—H2118.2C15—C16—C17105.92 (15)
N1—C3—C4122.90 (18)C15—C16—H16A110.6
N1—C3—H3118.6C17—C16—H16A110.6
C4—C3—H3118.6C15—C16—H16B110.6
C3—C4—C5119.27 (18)C17—C16—H16B110.6
C3—C4—H4120.4H16A—C16—H16B108.7
C5—C4—H4120.4C18—C17—C16113.87 (15)
C4—C5—C1117.80 (18)C18—C17—C19111.03 (15)
C4—C5—C6119.54 (18)C16—C17—C19107.34 (14)
C1—C5—C6122.65 (17)C18—C17—H17108.1
N2—C6—C5121.89 (18)C16—C17—H17108.1
N2—C6—H6119.1C19—C17—H17108.1
C5—C6—H6119.1O4—C18—O3123.60 (17)
N3—C7—C8119.25 (17)O4—C18—C17124.93 (16)
N3—C7—H7120.4O3—C18—C17111.43 (15)
C8—C7—H7120.4C22—C19—C21107.88 (15)
C12—C8—C9118.02 (18)C22—C19—C14114.56 (15)
C12—C8—C7121.01 (17)C21—C19—C14110.33 (14)
C9—C8—C7120.95 (17)C22—C19—C17110.82 (15)
C10—C9—C8119.23 (18)C21—C19—C17111.70 (14)
C10—C9—H9120.4C14—C19—C17101.53 (13)
C8—C9—H9120.4C14—C20—H20A109.5
N4—C10—C9122.99 (18)C14—C20—H20B109.5
N4—C10—H10118.5H20A—C20—H20B109.5
C9—C10—H10118.5C14—C20—H20C109.5
N4—C11—C12123.38 (18)H20A—C20—H20C109.5
N4—C11—H11118.3H20B—C20—H20C109.5
C12—C11—H11118.3C19—C21—H21A109.5
C11—C12—C8118.76 (18)C19—C21—H21B109.5
C11—C12—H12120.6H21A—C21—H21B109.5
C8—C12—H12120.6C19—C21—H21C109.5
C13—O1—H1C109.2 (17)H21A—C21—H21C109.5
C18—O3—H3C107 (2)H21B—C21—H21C109.5
O2—C13—O1122.76 (17)C19—C22—H22A109.5
O2—C13—C14124.23 (16)C19—C22—H22B109.5
O1—C13—C14113.01 (15)H22A—C22—H22B109.5
C13—C14—C15110.56 (14)C19—C22—H22C109.5
C13—C14—C20109.74 (14)H22A—C22—H22C109.5
C15—C14—C20110.15 (15)H22B—C22—H22C109.5
C6—N2—N3—C7177.80 (17)O2—C13—C14—C19112.1 (2)
C3—N1—C2—C11.2 (3)O1—C13—C14—C1966.97 (19)
C5—C1—C2—N11.5 (3)C13—C14—C15—C16159.19 (15)
C2—N1—C3—C40.0 (3)C20—C14—C15—C1679.35 (18)
N1—C3—C4—C50.8 (3)C19—C14—C15—C1640.33 (18)
C3—C4—C5—C10.4 (3)C14—C15—C16—C1725.12 (19)
C3—C4—C5—C6178.39 (17)C15—C16—C17—C18122.90 (17)
C2—C1—C5—C40.7 (3)C15—C16—C17—C190.42 (19)
C2—C1—C5—C6179.43 (17)C16—C17—C18—O418.5 (3)
N3—N2—C6—C5177.75 (16)C19—C17—C18—O4102.8 (2)
C4—C5—C6—N2174.22 (19)C16—C17—C18—O3163.84 (16)
C1—C5—C6—N24.5 (3)C19—C17—C18—O374.87 (19)
N2—N3—C7—C8177.63 (15)C13—C14—C19—C2283.18 (18)
N3—C7—C8—C12170.28 (18)C15—C14—C19—C22158.23 (15)
N3—C7—C8—C98.1 (3)C20—C14—C19—C2239.7 (2)
C12—C8—C9—C100.1 (3)C13—C14—C19—C2138.78 (19)
C7—C8—C9—C10178.56 (16)C15—C14—C19—C2179.81 (17)
C11—N4—C10—C90.9 (3)C20—C14—C19—C21161.67 (15)
C8—C9—C10—N40.9 (3)C13—C14—C19—C17157.34 (14)
C10—N4—C11—C120.2 (3)C15—C14—C19—C1738.75 (16)
N4—C11—C12—C80.6 (3)C20—C14—C19—C1779.77 (17)
C9—C8—C12—C110.6 (3)C18—C17—C19—C2289.36 (18)
C7—C8—C12—C11177.88 (17)C16—C17—C19—C22145.59 (15)
O2—C13—C14—C152.1 (3)C18—C17—C19—C2130.96 (19)
O1—C13—C14—C15178.81 (15)C16—C17—C19—C2194.09 (17)
O2—C13—C14—C20123.8 (2)C18—C17—C19—C14148.53 (14)
O1—C13—C14—C2057.11 (19)C16—C17—C19—C1423.49 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1C···N4i0.85 (3)1.86 (3)2.699 (2)169 (3)
O3—H3C···N1ii0.85 (3)1.84 (3)2.675 (2)167 (3)
Symmetry codes: (i) x+2, y1/2, z+1/2; (ii) x+1/2, y+3/2, z.
(ccp32) top
Crystal data top
3(C12H10N4)·2(C10H16O4)F(000) = 1092
Mr = 1031.18Dx = 1.325 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4895 reflections
a = 9.9568 (17) Åθ = 2.4–28.1°
b = 12.914 (2) ŵ = 0.09 mm1
c = 20.203 (4) ÅT = 110 K
β = 95.734 (3)°Block, yellow
V = 2584.7 (8) Å30.68 × 0.48 × 0.10 mm
Z = 2
Data collection top
Bruker SMART APEX CCD
diffractometer
9631 independent reflections
Radiation source: fine-focus sealed tube8918 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ω and φ scansθmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan
SADABS (Bruker, 2008)
h = 1012
Tmin = 0.941, Tmax = 0.991k = 1516
12491 measured reflectionsl = 2522
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0847P)2 + 1.6575P]
where P = (Fo2 + 2Fc2)/3
9631 reflections(Δ/σ)max = 0.001
695 parametersΔρmax = 0.39 e Å3
1 restraintΔρmin = 0.29 e Å3
Crystal data top
3(C12H10N4)·2(C10H16O4)V = 2584.7 (8) Å3
Mr = 1031.18Z = 2
Monoclinic, P21Mo Kα radiation
a = 9.9568 (17) ŵ = 0.09 mm1
b = 12.914 (2) ÅT = 110 K
c = 20.203 (4) Å0.68 × 0.48 × 0.10 mm
β = 95.734 (3)°
Data collection top
Bruker SMART APEX CCD
diffractometer
9631 independent reflections
Absorption correction: multi-scan
SADABS (Bruker, 2008)
8918 reflections with I > 2σ(I)
Tmin = 0.941, Tmax = 0.991Rint = 0.029
12491 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0711 restraint
wR(F2) = 0.178H-atom parameters constrained
S = 1.11Δρmax = 0.39 e Å3
9631 reflectionsΔρmin = 0.29 e Å3
695 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
O11.2428 (2)0.6358 (2)0.46591 (12)0.0213 (6)
H1C1.28460.67360.44270.032*
O21.0961 (3)0.6341 (3)0.37576 (13)0.0369 (8)
O30.8226 (3)0.5275 (2)0.64989 (12)0.0277 (7)
O40.6638 (3)0.5436 (3)0.56443 (12)0.0295 (7)
H4C0.62010.56800.59300.044*
O50.6886 (3)0.4666 (3)0.85365 (13)0.0312 (7)
O60.8385 (2)0.4669 (3)0.94262 (13)0.0275 (7)
H6C0.88780.44400.91590.041*
O70.2698 (2)0.3594 (2)1.03924 (12)0.0236 (6)
H7C0.22580.32601.06400.035*
O80.4103 (3)0.3809 (2)1.13210 (12)0.0262 (6)
N10.1893 (4)1.1378 (3)0.9240 (2)0.0383 (9)
N20.1174 (3)0.9157 (3)0.80028 (17)0.0307 (8)
N30.1737 (3)0.8654 (3)0.74784 (17)0.0295 (8)
N40.5106 (3)0.6357 (3)0.64606 (16)0.0253 (8)
N50.6086 (3)0.2565 (2)0.60750 (14)0.0170 (6)
N60.2791 (3)0.4743 (3)0.72367 (15)0.0196 (7)
N70.2335 (3)0.5324 (3)0.77666 (15)0.0179 (7)
N80.1069 (3)0.7468 (3)0.88922 (16)0.0224 (7)
N90.6933 (4)0.1350 (3)0.59125 (18)0.0343 (9)
N100.3850 (3)0.0986 (3)0.70498 (16)0.0247 (7)
N110.3252 (3)0.1482 (3)0.75705 (15)0.0241 (7)
N120.0144 (3)0.3692 (3)0.86052 (16)0.0263 (8)
C10.1544 (4)1.1012 (4)0.8099 (2)0.0325 (10)
H10.17941.11440.76510.039*
C20.2155 (4)1.1532 (3)0.8591 (3)0.0370 (11)
H20.28011.20280.84540.044*
C30.0942 (4)1.0673 (3)0.9420 (2)0.0291 (9)
H30.07241.05560.98720.035*
C40.0266 (4)1.0112 (4)0.8980 (2)0.0274 (9)
H40.03710.96190.91340.033*
C50.0548 (4)1.0292 (3)0.8295 (2)0.0282 (9)
C60.0180 (4)0.9731 (4)0.7808 (2)0.0287 (9)
H60.00900.97980.73560.034*
C70.2843 (4)0.8212 (3)0.76873 (19)0.0249 (9)
H70.31740.82810.81320.030*
C80.3606 (4)0.7594 (3)0.7242 (2)0.0230 (8)
C90.4763 (4)0.7073 (3)0.75123 (18)0.0224 (8)
H90.50500.71280.79630.027*
C100.5475 (4)0.6475 (3)0.71020 (19)0.0231 (8)
H100.62510.61390.72860.028*
C110.3987 (4)0.6856 (4)0.62037 (19)0.0290 (10)
H110.37170.67810.57520.035*
C120.3226 (4)0.7466 (4)0.65752 (19)0.0273 (9)
H120.24550.77930.63770.033*
C130.5971 (3)0.3409 (3)0.71182 (18)0.0208 (8)
H130.63880.35680.75380.025*
C140.6639 (4)0.2830 (3)0.66847 (18)0.0221 (8)
H140.75140.26130.68190.027*
C150.4828 (4)0.2887 (3)0.58927 (17)0.0175 (7)
H150.44310.27070.54720.021*
C160.4086 (3)0.3476 (3)0.62980 (17)0.0179 (8)
H160.32110.36820.61530.021*
C170.4674 (3)0.3753 (3)0.69260 (17)0.0152 (7)
C180.3977 (3)0.4375 (3)0.73973 (17)0.0174 (8)
H180.44040.45050.78200.021*
C190.1171 (3)0.5698 (3)0.75995 (17)0.0177 (8)
H190.07650.55810.71710.021*
C200.0442 (3)0.6313 (3)0.80636 (17)0.0167 (7)
C210.0866 (3)0.6630 (3)0.78496 (18)0.0206 (8)
H210.12620.64620.74270.025*
C220.1567 (4)0.7208 (3)0.82872 (19)0.0224 (8)
H220.24380.74230.81420.027*
C230.0198 (3)0.7167 (3)0.90946 (18)0.0213 (8)
H230.05690.73560.95180.026*
C240.0976 (4)0.6585 (3)0.86985 (18)0.0216 (8)
H240.18440.63810.88580.026*
C250.6610 (4)0.0848 (4)0.7025 (2)0.0309 (9)
H250.68580.09300.74780.037*
C260.7245 (4)0.1413 (4)0.6563 (2)0.0337 (10)
H260.79330.18640.67200.040*
C270.5969 (4)0.0680 (4)0.5700 (2)0.0330 (10)
H270.57480.06180.52440.040*
C280.5274 (4)0.0071 (3)0.61141 (19)0.0250 (9)
H280.46090.03850.59380.030*
C290.5589 (4)0.0152 (3)0.67975 (19)0.0226 (8)
C300.4859 (4)0.0424 (3)0.72710 (18)0.0224 (8)
H300.51220.03840.77250.027*
C310.2160 (4)0.1917 (3)0.7350 (2)0.0243 (9)
H310.18630.18620.69000.029*
C320.1350 (4)0.2507 (3)0.77874 (18)0.0191 (8)
C330.0279 (4)0.3116 (3)0.75205 (18)0.0222 (8)
H330.00400.31340.70640.027*
C340.0422 (4)0.3693 (3)0.7947 (2)0.0257 (9)
H340.11290.41060.77640.031*
C350.0883 (4)0.3087 (4)0.88620 (19)0.0297 (10)
H350.10890.30760.93210.036*
C360.1642 (4)0.2485 (3)0.8475 (2)0.0254 (9)
H360.23360.20710.86710.030*
C370.7851 (3)0.5208 (3)0.59085 (19)0.0203 (8)
C380.8773 (3)0.4842 (3)0.53852 (16)0.0149 (7)
C391.0106 (3)0.4350 (3)0.56976 (17)0.0187 (7)
H39A1.03440.46220.61410.022*
H39B1.00140.36040.57260.022*
C401.1200 (3)0.4635 (3)0.52369 (16)0.0154 (6)
H40A1.19200.50300.54770.019*
H40B1.15830.40150.50600.019*
C411.0473 (3)0.5285 (3)0.46752 (17)0.0160 (7)
H411.00700.47970.43400.019*
C421.1301 (4)0.6047 (3)0.43149 (17)0.0199 (8)
C430.9273 (3)0.5810 (3)0.50009 (17)0.0170 (7)
C440.7998 (4)0.4074 (3)0.49226 (18)0.0230 (8)
H44A0.77300.34940.51760.035*
H44B0.85640.38380.45950.035*
H44C0.72110.44040.47040.035*
C450.9794 (3)0.6662 (3)0.54842 (17)0.0184 (7)
H45A1.02300.71890.52470.028*
H45B1.04290.63720.58230.028*
H45C0.90510.69600.56860.028*
C460.8229 (3)0.6279 (3)0.44886 (18)0.0234 (8)
H46A0.74740.65230.47060.035*
H46B0.79280.57630.41650.035*
H46C0.86240.68480.42710.035*
C470.7162 (4)0.4826 (3)0.91225 (17)0.0180 (8)
C480.6130 (3)0.5179 (3)0.95726 (16)0.0156 (7)
C490.6635 (4)0.5694 (3)1.02424 (19)0.0279 (9)
H49A0.67490.64341.01850.033*
H49B0.74930.54001.04190.033*
C500.5516 (4)0.5472 (3)1.07278 (18)0.0277 (8)
H50A0.59040.51381.11330.033*
H50B0.50770.61081.08430.033*
C510.4522 (3)0.4754 (3)1.03298 (16)0.0151 (7)
H510.38400.51941.00850.018*
C520.3776 (3)0.4004 (3)1.07447 (18)0.0169 (7)
C530.5329 (4)0.4224 (3)0.98113 (18)0.0220 (8)
C540.5194 (4)0.5952 (3)0.9176 (2)0.0291 (9)
H54A0.57050.65490.90680.044*
H54B0.44890.61610.94380.044*
H54C0.48050.56300.87730.044*
C550.6250 (4)0.3407 (3)1.0125 (2)0.0327 (9)
H55A0.67630.31100.97950.049*
H55B0.57250.28761.03100.049*
H55C0.68530.37111.04720.049*
C560.4404 (4)0.3727 (3)0.92377 (19)0.0312 (9)
H56A0.49370.35170.88910.047*
H56B0.37400.42220.90650.047*
H56C0.39600.31330.94020.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0247 (13)0.0231 (15)0.0171 (12)0.0045 (11)0.0075 (10)0.0028 (12)
O20.0354 (15)0.051 (2)0.0237 (15)0.0113 (14)0.0024 (12)0.0165 (15)
O30.0366 (15)0.0356 (18)0.0121 (12)0.0042 (13)0.0086 (10)0.0037 (12)
O40.0279 (14)0.042 (2)0.0203 (13)0.0019 (13)0.0121 (11)0.0077 (13)
O50.0330 (14)0.0398 (19)0.0223 (14)0.0034 (13)0.0106 (11)0.0072 (13)
O60.0170 (12)0.0339 (18)0.0327 (14)0.0018 (12)0.0079 (10)0.0120 (14)
O70.0251 (13)0.0265 (16)0.0203 (13)0.0094 (11)0.0083 (10)0.0036 (12)
O80.0254 (13)0.0361 (18)0.0171 (13)0.0031 (12)0.0026 (10)0.0117 (12)
N10.044 (2)0.027 (2)0.045 (2)0.0048 (17)0.0105 (17)0.0067 (18)
N20.0387 (19)0.027 (2)0.0286 (18)0.0020 (16)0.0151 (15)0.0007 (17)
N30.0296 (18)0.030 (2)0.0298 (18)0.0008 (15)0.0085 (14)0.0003 (17)
N40.0229 (15)0.025 (2)0.0301 (17)0.0044 (14)0.0122 (13)0.0047 (16)
N50.0199 (14)0.0147 (17)0.0179 (15)0.0014 (12)0.0094 (12)0.0010 (13)
N60.0234 (15)0.0170 (17)0.0190 (15)0.0046 (13)0.0044 (12)0.0039 (14)
N70.0161 (14)0.0195 (18)0.0194 (15)0.0004 (12)0.0078 (11)0.0065 (13)
N80.0250 (15)0.0181 (18)0.0256 (17)0.0006 (13)0.0090 (13)0.0024 (14)
N90.050 (2)0.022 (2)0.035 (2)0.0025 (16)0.0246 (16)0.0028 (16)
N100.0260 (16)0.0245 (19)0.0243 (16)0.0022 (14)0.0065 (13)0.0066 (15)
N110.0315 (17)0.023 (2)0.0196 (15)0.0019 (15)0.0115 (13)0.0040 (15)
N120.0250 (16)0.031 (2)0.0236 (16)0.0041 (14)0.0057 (13)0.0092 (16)
C10.032 (2)0.023 (2)0.042 (2)0.0028 (17)0.0028 (18)0.007 (2)
C20.032 (2)0.014 (2)0.065 (3)0.0109 (17)0.003 (2)0.003 (2)
C30.030 (2)0.019 (2)0.040 (2)0.0014 (16)0.0059 (17)0.0005 (19)
C40.0196 (17)0.026 (2)0.037 (2)0.0024 (16)0.0001 (16)0.0002 (19)
C50.0232 (19)0.020 (2)0.043 (2)0.0037 (16)0.0116 (16)0.0058 (19)
C60.0256 (19)0.029 (2)0.033 (2)0.0038 (17)0.0083 (16)0.0038 (19)
C70.034 (2)0.021 (2)0.0205 (18)0.0073 (17)0.0086 (16)0.0025 (18)
C80.0197 (18)0.020 (2)0.030 (2)0.0071 (15)0.0082 (15)0.0024 (17)
C90.0228 (17)0.028 (2)0.0164 (17)0.0136 (16)0.0030 (14)0.0055 (16)
C100.0209 (17)0.023 (2)0.0251 (19)0.0070 (15)0.0005 (14)0.0016 (17)
C110.039 (2)0.034 (3)0.0147 (17)0.0046 (18)0.0044 (16)0.0000 (17)
C120.035 (2)0.028 (2)0.0207 (19)0.0016 (17)0.0084 (16)0.0083 (18)
C130.0147 (16)0.027 (2)0.0205 (17)0.0024 (15)0.0015 (13)0.0027 (17)
C140.0210 (18)0.023 (2)0.0228 (19)0.0035 (15)0.0059 (15)0.0011 (17)
C150.0287 (18)0.0143 (19)0.0099 (16)0.0031 (15)0.0037 (14)0.0022 (15)
C160.0185 (17)0.018 (2)0.0174 (17)0.0022 (14)0.0028 (13)0.0047 (16)
C170.0194 (16)0.0113 (19)0.0153 (16)0.0008 (14)0.0031 (13)0.0015 (15)
C180.0177 (16)0.019 (2)0.0163 (17)0.0028 (14)0.0055 (13)0.0014 (15)
C190.0230 (17)0.016 (2)0.0142 (16)0.0012 (14)0.0022 (13)0.0058 (15)
C200.0191 (16)0.0107 (19)0.0216 (17)0.0005 (13)0.0083 (13)0.0011 (16)
C210.0220 (17)0.020 (2)0.0195 (17)0.0016 (15)0.0014 (14)0.0075 (16)
C220.0195 (17)0.020 (2)0.028 (2)0.0038 (15)0.0033 (15)0.0026 (18)
C230.0194 (17)0.024 (2)0.0203 (18)0.0012 (15)0.0004 (14)0.0051 (17)
C240.0209 (18)0.024 (2)0.0211 (18)0.0017 (16)0.0060 (14)0.0003 (17)
C250.036 (2)0.026 (2)0.032 (2)0.0020 (18)0.0121 (17)0.0004 (19)
C260.044 (2)0.026 (2)0.035 (2)0.0074 (19)0.0185 (18)0.0084 (19)
C270.043 (2)0.033 (3)0.025 (2)0.008 (2)0.0136 (18)0.0075 (19)
C280.031 (2)0.017 (2)0.029 (2)0.0049 (16)0.0132 (16)0.0036 (17)
C290.0280 (19)0.013 (2)0.0283 (19)0.0064 (15)0.0102 (15)0.0010 (16)
C300.0313 (19)0.019 (2)0.0172 (17)0.0053 (16)0.0060 (14)0.0005 (16)
C310.0256 (19)0.027 (2)0.0215 (18)0.0046 (16)0.0093 (15)0.0007 (18)
C320.0246 (18)0.016 (2)0.0177 (17)0.0035 (15)0.0072 (14)0.0013 (16)
C330.0274 (19)0.027 (2)0.0127 (17)0.0054 (16)0.0039 (14)0.0034 (16)
C340.0182 (17)0.022 (2)0.038 (2)0.0000 (15)0.0086 (15)0.0046 (19)
C350.028 (2)0.045 (3)0.0167 (18)0.0027 (18)0.0057 (15)0.0064 (19)
C360.0257 (18)0.025 (2)0.026 (2)0.0026 (16)0.0053 (15)0.0005 (18)
C370.0195 (17)0.014 (2)0.028 (2)0.0073 (14)0.0094 (14)0.0012 (17)
C380.0213 (16)0.0108 (19)0.0128 (15)0.0023 (13)0.0025 (13)0.0030 (15)
C390.0263 (17)0.0144 (19)0.0159 (16)0.0024 (14)0.0052 (13)0.0004 (14)
C400.0182 (15)0.0108 (17)0.0175 (15)0.0033 (12)0.0024 (12)0.0054 (13)
C410.0217 (17)0.0117 (19)0.0149 (16)0.0029 (14)0.0037 (13)0.0036 (15)
C420.0247 (17)0.022 (2)0.0142 (16)0.0045 (16)0.0066 (13)0.0028 (16)
C430.0229 (16)0.0114 (18)0.0186 (16)0.0001 (13)0.0106 (13)0.0006 (14)
C440.0315 (19)0.0172 (19)0.0217 (18)0.0032 (15)0.0093 (14)0.0007 (15)
C450.0187 (15)0.0137 (17)0.0227 (17)0.0016 (13)0.0020 (13)0.0007 (15)
C460.0191 (16)0.025 (2)0.0261 (18)0.0010 (14)0.0009 (13)0.0106 (16)
C470.0257 (18)0.016 (2)0.0128 (16)0.0072 (15)0.0028 (13)0.0046 (15)
C480.0212 (17)0.0134 (19)0.0127 (15)0.0066 (14)0.0040 (13)0.0030 (15)
C490.033 (2)0.022 (2)0.030 (2)0.0011 (16)0.0064 (16)0.0055 (18)
C500.040 (2)0.017 (2)0.0256 (19)0.0051 (16)0.0012 (15)0.0021 (16)
C510.0218 (17)0.0135 (19)0.0108 (15)0.0024 (14)0.0056 (13)0.0018 (15)
C520.0174 (16)0.0128 (19)0.0217 (18)0.0015 (14)0.0074 (13)0.0001 (16)
C530.035 (2)0.0065 (18)0.0276 (19)0.0026 (14)0.0204 (16)0.0020 (15)
C540.0323 (19)0.025 (2)0.028 (2)0.0005 (16)0.0039 (16)0.0089 (18)
C550.040 (2)0.021 (2)0.041 (2)0.0060 (17)0.0215 (18)0.0063 (19)
C560.047 (2)0.022 (2)0.0268 (19)0.0158 (17)0.0157 (17)0.0091 (17)
Geometric parameters (Å, º) top
O1—C421.322 (4)C23—H230.9300
O1—H1C0.8200C24—H240.9300
O2—C421.204 (4)C25—C261.386 (6)
O3—C371.217 (4)C25—C291.400 (6)
O4—C371.305 (4)C25—H250.9300
O4—H4C0.8200C26—H260.9300
O5—C471.206 (4)C27—C281.383 (5)
O6—C471.324 (4)C27—H270.9300
O6—H6C0.8200C28—C291.389 (6)
O7—C521.336 (4)C28—H280.9300
O7—H7C0.8200C29—C301.461 (5)
O8—C521.204 (4)C30—H300.9300
N1—C21.326 (6)C31—C321.468 (5)
N1—C31.337 (5)C31—H310.9300
N2—C61.268 (5)C32—C331.389 (6)
N2—N31.406 (5)C32—C361.392 (5)
N3—C71.274 (5)C33—C341.381 (5)
N4—C101.320 (5)C33—H330.9300
N4—C111.345 (5)C34—H340.9300
N5—C151.336 (5)C35—C361.380 (5)
N5—C141.343 (5)C35—H350.9300
N6—C181.283 (5)C36—H360.9300
N6—N71.419 (3)C37—C381.542 (5)
N7—C191.270 (5)C38—C441.519 (5)
N8—C221.315 (5)C38—C391.548 (5)
N8—C231.345 (5)C38—C431.578 (5)
N9—C261.322 (6)C39—C401.546 (4)
N9—C271.331 (6)C39—H39A0.9700
N10—C301.283 (5)C39—H39B0.9700
N10—N111.413 (4)C40—C411.534 (5)
N11—C311.265 (5)C40—H40A0.9700
N12—C341.331 (5)C40—H40B0.9700
N12—C351.348 (5)C41—C421.516 (5)
C1—C21.389 (6)C41—C431.574 (4)
C1—C51.388 (6)C41—H410.9800
C1—H10.9300C43—C461.518 (5)
C2—H20.9300C43—C451.527 (5)
C3—C41.374 (6)C44—H44A0.9600
C3—H30.9300C44—H44B0.9600
C4—C51.403 (6)C44—H44C0.9600
C4—H40.9300C45—H45A0.9600
C5—C61.469 (6)C45—H45B0.9600
C6—H60.9300C45—H45C0.9600
C7—C81.470 (5)C46—H46A0.9600
C7—H70.9300C46—H46B0.9600
C8—C121.372 (5)C46—H46C0.9600
C8—C91.397 (6)C47—C481.509 (5)
C9—C101.380 (5)C48—C541.536 (5)
C9—H90.9300C48—C491.546 (5)
C10—H100.9300C48—C531.571 (5)
C11—C121.369 (6)C49—C501.582 (5)
C11—H110.9300C49—H49A0.9700
C12—H120.9300C49—H49B0.9700
C13—C141.372 (5)C50—C511.525 (5)
C13—C171.384 (5)C50—H50A0.9700
C13—H130.9300C50—H50B0.9700
C14—H140.9300C51—C521.522 (5)
C15—C161.384 (5)C51—C531.543 (4)
C15—H150.9300C51—H510.9800
C16—C171.390 (5)C53—C551.496 (5)
C16—H160.9300C53—C561.546 (5)
C17—C181.472 (4)C54—H54A0.9600
C18—H180.9300C54—H54B0.9600
C19—C201.473 (5)C54—H54C0.9600
C19—H190.9300C55—H55A0.9600
C20—C241.384 (5)C55—H55B0.9600
C20—C211.393 (5)C55—H55C0.9600
C21—C221.396 (5)C56—H56A0.9600
C21—H210.9300C56—H56B0.9600
C22—H220.9300C56—H56C0.9600
C23—C241.389 (5)
C42—O1—H1C109.5N12—C34—H34118.1
C37—O4—H4C109.5C33—C34—H34118.1
C47—O6—H6C109.5N12—C35—C36123.1 (4)
C52—O7—H7C109.5N12—C35—H35118.5
C2—N1—C3115.8 (4)C36—C35—H35118.5
C6—N2—N3113.2 (3)C35—C36—C32118.8 (4)
C7—N3—N2110.7 (3)C35—C36—H36120.6
C10—N4—C11117.6 (3)C32—C36—H36120.6
C15—N5—C14117.4 (3)O3—C37—O4124.4 (3)
C18—N6—N7111.1 (3)O3—C37—C38123.3 (3)
C19—N7—N6110.7 (3)O4—C37—C38112.3 (3)
C22—N8—C23117.6 (3)C44—C38—C37108.7 (3)
C26—N9—C27116.8 (4)C44—C38—C39110.2 (3)
C30—N10—N11111.8 (3)C37—C38—C39113.0 (3)
C31—N11—N10110.5 (3)C44—C38—C43112.3 (3)
C34—N12—C35117.3 (3)C37—C38—C43109.4 (3)
C2—C1—C5118.1 (4)C39—C38—C43103.1 (3)
C2—C1—H1120.9C40—C39—C38106.5 (3)
C5—C1—H1120.9C40—C39—H39A110.4
N1—C2—C1125.3 (4)C38—C39—H39A110.4
N1—C2—H2117.3C40—C39—H39B110.4
C1—C2—H2117.3C38—C39—H39B110.4
N1—C3—C4124.3 (4)H39A—C39—H39B108.6
N1—C3—H3117.9C41—C40—C39105.4 (2)
C4—C3—H3117.9C41—C40—H40A110.7
C3—C4—C5119.2 (4)C39—C40—H40A110.7
C3—C4—H4120.4C41—C40—H40B110.7
C5—C4—H4120.4C39—C40—H40B110.7
C1—C5—C4117.3 (4)H40A—C40—H40B108.8
C1—C5—C6121.7 (4)C42—C41—C40118.1 (3)
C4—C5—C6121.0 (4)C42—C41—C43113.1 (3)
N2—C6—C5120.2 (4)C40—C41—C43104.4 (3)
N2—C6—H6119.9C42—C41—H41106.9
C5—C6—H6119.9C40—C41—H41106.9
N3—C7—C8121.5 (4)C43—C41—H41106.9
N3—C7—H7119.2O2—C42—O1122.7 (4)
C8—C7—H7119.2O2—C42—C41122.6 (3)
C12—C8—C9117.5 (4)O1—C42—C41114.7 (3)
C12—C8—C7123.9 (4)C46—C43—C45108.3 (3)
C9—C8—C7118.6 (4)C46—C43—C41112.6 (3)
C10—C9—C8119.2 (3)C45—C43—C41110.7 (3)
C10—C9—H9120.4C46—C43—C38115.0 (3)
C8—C9—H9120.4C45—C43—C38111.1 (3)
N4—C10—C9123.0 (4)C41—C43—C3898.8 (3)
N4—C10—H10118.5C38—C44—H44A109.5
C9—C10—H10118.5C38—C44—H44B109.5
N4—C11—C12123.1 (4)H44A—C44—H44B109.5
N4—C11—H11118.4C38—C44—H44C109.5
C12—C11—H11118.4H44A—C44—H44C109.5
C11—C12—C8119.6 (4)H44B—C44—H44C109.5
C11—C12—H12120.2C43—C45—H45A109.5
C8—C12—H12120.2C43—C45—H45B109.5
C14—C13—C17119.6 (3)H45A—C45—H45B109.5
C14—C13—H13120.2C43—C45—H45C109.5
C17—C13—H13120.2H45A—C45—H45C109.5
N5—C14—C13123.0 (3)H45B—C45—H45C109.5
N5—C14—H14118.5C43—C46—H46A109.5
C13—C14—H14118.5C43—C46—H46B109.5
N5—C15—C16123.3 (3)H46A—C46—H46B109.5
N5—C15—H15118.3C43—C46—H46C109.5
C16—C15—H15118.3H46A—C46—H46C109.5
C15—C16—C17118.7 (3)H46B—C46—H46C109.5
C15—C16—H16120.6O5—C47—O6122.5 (3)
C17—C16—H16120.6O5—C47—C48122.8 (3)
C13—C17—C16118.0 (3)O6—C47—C48114.7 (3)
C13—C17—C18118.8 (3)C47—C48—C54107.2 (3)
C16—C17—C18123.2 (3)C47—C48—C49118.4 (3)
N6—C18—C17121.3 (3)C54—C48—C49107.7 (3)
N6—C18—H18119.3C47—C48—C53110.1 (3)
C17—C18—H18119.3C54—C48—C53111.8 (3)
N7—C19—C20122.0 (3)C49—C48—C53101.5 (3)
N7—C19—H19119.0C48—C49—C50106.1 (3)
C20—C19—H19119.0C48—C49—H49A110.5
C24—C20—C21118.3 (3)C50—C49—H49A110.5
C24—C20—C19124.0 (3)C48—C49—H49B110.5
C21—C20—C19117.7 (3)C50—C49—H49B110.5
C20—C21—C22118.2 (3)H49A—C49—H49B108.7
C20—C21—H21120.9C51—C50—C49104.1 (3)
C22—C21—H21120.9C51—C50—H50A110.9
N8—C22—C21124.0 (3)C49—C50—H50A110.9
N8—C22—H22118.0C51—C50—H50B110.9
C21—C22—H22118.0C49—C50—H50B110.9
N8—C23—C24122.8 (3)H50A—C50—H50B109.0
N8—C23—H23118.6C52—C51—C50115.0 (3)
C24—C23—H23118.6C52—C51—C53114.0 (3)
C20—C24—C23119.1 (3)C50—C51—C53105.8 (3)
C20—C24—H24120.4C52—C51—H51107.2
C23—C24—H24120.4C50—C51—H51107.2
C26—C25—C29118.8 (4)C53—C51—H51107.2
C26—C25—H25120.6O8—C52—O7123.9 (3)
C29—C25—H25120.6O8—C52—C51124.5 (3)
N9—C26—C25124.0 (4)O7—C52—C51111.7 (3)
N9—C26—H26118.0C55—C53—C51111.4 (3)
C25—C26—H26118.0C55—C53—C56108.6 (3)
N9—C27—C28124.3 (4)C51—C53—C56112.4 (3)
N9—C27—H27117.9C55—C53—C48112.0 (3)
C28—C27—H27117.9C51—C53—C48100.0 (3)
C27—C28—C29118.8 (4)C56—C53—C48112.3 (3)
C27—C28—H28120.6C48—C54—H54A109.5
C29—C28—H28120.6C48—C54—H54B109.5
C28—C29—C25117.3 (4)H54A—C54—H54B109.5
C28—C29—C30122.3 (4)C48—C54—H54C109.5
C25—C29—C30120.3 (4)H54A—C54—H54C109.5
N10—C30—C29118.9 (3)H54B—C54—H54C109.5
N10—C30—H30120.6C53—C55—H55A109.5
C29—C30—H30120.6C53—C55—H55B109.5
N11—C31—C32121.5 (4)H55A—C55—H55B109.5
N11—C31—H31119.2C53—C55—H55C109.5
C32—C31—H31119.2H55A—C55—H55C109.5
C33—C32—C36118.4 (3)H55B—C55—H55C109.5
C33—C32—C31120.4 (3)C53—C56—H56A109.5
C36—C32—C31121.2 (4)C53—C56—H56B109.5
C34—C33—C32118.6 (3)H56A—C56—H56B109.5
C34—C33—H33120.7C53—C56—H56C109.5
C32—C33—H33120.7H56A—C56—H56C109.5
N12—C34—C33123.7 (4)H56B—C56—H56C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1C···N5i0.821.882.694 (4)176
O4—H4C···N40.821.832.639 (4)171
O6—H6C···N12ii0.821.832.641 (4)169
O7—H7C···N8iii0.821.892.702 (4)172
Symmetry codes: (i) x+2, y+1/2, z+1; (ii) x+1, y, z; (iii) x, y1/2, z+2.
(ccr32) top
Crystal data top
3(C12H10N4)·2(C10H16O4)F(000) = 1092
Mr = 1031.18Dx = 1.320 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4215 reflections
a = 9.9407 (10) Åθ = 2.4–28.2°
b = 12.9624 (13) ŵ = 0.09 mm1
c = 20.247 (2) ÅT = 150 K
β = 95.928 (2)°Plate, yellow
V = 2595.0 (4) Å30.23 × 0.11 × 0.04 mm
Z = 2
Data collection top
Bruker SMART APEX CCD
diffractometer
4541 independent reflections
Radiation source: fine-focus sealed tube3787 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω and φ scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
SADABS (Bruker, 2008)
h = 119
Tmin = 0.979, Tmax = 0.996k = 1513
12644 measured reflectionsl = 2024
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.12 w = 1/[σ2(Fo2) + (0.0459P)2 + 0.8495P]
where P = (Fo2 + 2Fc2)/3
4541 reflections(Δ/σ)max < 0.001
412 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
3(C12H10N4)·2(C10H16O4)V = 2595.0 (4) Å3
Mr = 1031.18Z = 2
Monoclinic, P21/nMo Kα radiation
a = 9.9407 (10) ŵ = 0.09 mm1
b = 12.9624 (13) ÅT = 150 K
c = 20.247 (2) Å0.23 × 0.11 × 0.04 mm
β = 95.928 (2)°
Data collection top
Bruker SMART APEX CCD
diffractometer
4541 independent reflections
Absorption correction: multi-scan
SADABS (Bruker, 2008)
3787 reflections with I > 2σ(I)
Tmin = 0.979, Tmax = 0.996Rint = 0.027
12644 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.12Δρmax = 0.19 e Å3
4541 reflectionsΔρmin = 0.18 e Å3
412 parameters
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.08958 (13)0.95695 (12)0.30786 (7)0.0430 (4)
H1C0.145 (3)0.927 (2)0.3421 (14)0.081 (8)*
O20.06248 (14)0.96506 (12)0.39631 (6)0.0461 (4)
O30.48108 (13)0.85649 (11)0.21087 (7)0.0390 (3)
H3C0.537 (3)0.816 (2)0.1830 (13)0.074 (8)*
O40.34053 (14)0.87419 (12)0.11849 (7)0.0486 (4)
C130.03267 (18)0.97642 (14)0.33711 (9)0.0306 (4)
C180.37294 (18)0.89556 (14)0.17641 (9)0.0303 (4)
C140.13302 (17)1.01288 (13)0.29066 (8)0.0256 (4)0.641 (3)
C150.0824 (5)1.0627 (4)0.2244 (2)0.0340 (10)0.641 (3)
H15A0.07091.13790.23000.041*0.641 (3)
H15B0.00581.03270.20690.041*0.641 (3)
C160.1914 (3)1.0406 (2)0.17567 (13)0.0297 (7)0.641 (3)
H16A0.15061.00520.13510.036*0.641 (3)
H16B0.23421.10550.16270.036*0.641 (3)
C170.29606 (17)0.97009 (13)0.21587 (8)0.0259 (4)0.641 (3)
H170.36471.01670.24000.031*0.641 (3)
C190.2182 (5)0.9192 (5)0.2687 (3)0.0262 (11)0.641 (3)
C200.2259 (5)1.0915 (3)0.3320 (2)0.0344 (10)0.641 (3)
H20A0.17191.15080.34360.052*0.641 (3)
H20B0.29741.11500.30560.052*0.641 (3)
H20C0.26671.05820.37270.052*0.641 (3)
C210.1232 (3)0.8348 (2)0.23736 (18)0.0368 (8)0.641 (3)
H21A0.05780.86570.20350.055*0.641 (3)
H21B0.07490.80270.27180.055*0.641 (3)
H21C0.17630.78240.21680.055*0.641 (3)
C220.3108 (4)0.8700 (2)0.32544 (15)0.0371 (9)0.641 (3)
H22A0.25650.84790.36070.056*0.641 (3)
H22B0.37830.92050.34330.056*0.641 (3)
H22C0.35670.81010.30860.056*0.641 (3)
C14A0.13302 (17)1.01288 (13)0.29066 (8)0.0256 (4)0.359 (3)
C15A0.2615 (9)1.0605 (6)0.3191 (4)0.0293 (17)0.359 (3)
H15C0.28591.03490.36480.035*0.359 (3)
H15D0.25141.13640.32090.035*0.359 (3)
C16A0.3721 (5)1.0320 (4)0.2749 (2)0.0272 (13)0.359 (3)
H16C0.44260.98890.29960.033*0.359 (3)
H16D0.41501.09460.25860.033*0.359 (3)
C17A0.29606 (17)0.97009 (13)0.21587 (8)0.0259 (4)0.359 (3)
H17A0.25281.02190.18380.031*0.359 (3)
C19A0.1770 (9)0.9146 (9)0.2498 (5)0.023 (2)0.359 (3)
C20A0.0546 (12)1.0923 (8)0.2435 (5)0.051 (2)0.359 (3)
H20D0.02011.14790.26990.077*0.359 (3)
H20E0.02111.05780.21760.077*0.359 (3)
H20F0.11571.12130.21330.077*0.359 (3)
C21A0.0722 (5)0.8724 (5)0.1967 (3)0.0352 (14)0.359 (3)
H21D0.11110.81460.17390.053*0.359 (3)
H21E0.04490.92690.16460.053*0.359 (3)
H21F0.00700.84850.21750.053*0.359 (3)
C22A0.2300 (5)0.8308 (4)0.2974 (3)0.0272 (13)0.359 (3)
H22D0.15440.79900.31740.041*0.359 (3)
H22E0.29370.86070.33240.041*0.359 (3)
H22F0.27630.77820.27330.041*0.359 (3)
N10.55714 (19)1.13128 (14)0.16838 (10)0.0524 (5)
N20.86784 (17)0.90730 (13)0.04956 (8)0.0417 (4)
N30.92698 (17)0.85981 (13)0.00306 (8)0.0416 (4)
N41.26097 (16)0.63882 (13)0.11011 (8)0.0391 (4)
C10.72220 (19)1.00527 (15)0.14525 (10)0.0375 (5)
H10.78860.95660.16200.045*
C20.6521 (2)1.06189 (16)0.18776 (11)0.0454 (5)
H20.67261.05080.23410.055*
C30.5301 (2)1.14399 (17)0.10304 (13)0.0521 (6)
H30.46231.19250.08770.063*
C40.5944 (2)1.09107 (16)0.05624 (11)0.0438 (5)
H40.57051.10290.01020.053*
C50.69429 (18)1.02052 (14)0.07732 (10)0.0357 (5)
C60.7686 (2)0.96519 (15)0.02916 (10)0.0386 (5)
H60.74270.97260.01710.046*
C71.03603 (19)0.81378 (15)0.01796 (10)0.0365 (5)
H71.06760.81700.06380.044*
C81.11376 (18)0.75588 (14)0.02731 (9)0.0313 (4)
C91.0808 (2)0.75541 (17)0.09512 (9)0.0409 (5)
H91.00700.79530.11460.049*
C101.1560 (2)0.69647 (18)0.13417 (10)0.0461 (5)
H101.13190.69680.18080.055*
C111.29345 (19)0.64035 (15)0.04475 (10)0.0382 (5)
H111.36860.60040.02670.046*
C121.22359 (18)0.69691 (15)0.00190 (10)0.0358 (5)
H121.25030.69560.04450.043*
N50.64034 (15)0.74245 (11)0.14003 (7)0.0312 (4)
N60.97686 (15)0.52846 (11)0.02657 (7)0.0299 (3)
C230.84243 (18)0.65255 (14)0.12027 (9)0.0309 (4)
H230.93110.63090.13640.037*
C240.76608 (18)0.71014 (14)0.15968 (9)0.0327 (4)
H240.80460.72790.20310.039*
C250.58888 (18)0.71799 (15)0.07868 (9)0.0344 (4)
H250.50010.74090.06390.041*
C260.65784 (18)0.66117 (14)0.03571 (9)0.0332 (4)
H260.61720.64570.00770.040*
C270.78775 (17)0.62668 (13)0.05656 (8)0.0267 (4)
C280.85970 (17)0.56555 (14)0.01009 (9)0.0286 (4)
H280.81750.55340.03350.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0310 (8)0.0558 (9)0.0439 (8)0.0009 (6)0.0112 (6)0.0082 (7)
O20.0477 (9)0.0635 (10)0.0291 (8)0.0068 (7)0.0139 (6)0.0108 (7)
O30.0385 (8)0.0440 (8)0.0364 (8)0.0127 (6)0.0131 (6)0.0018 (6)
O40.0479 (9)0.0612 (10)0.0376 (8)0.0080 (7)0.0085 (7)0.0192 (7)
C130.0333 (10)0.0292 (10)0.0307 (10)0.0090 (8)0.0096 (8)0.0017 (8)
C180.0329 (10)0.0286 (10)0.0311 (10)0.0026 (8)0.0119 (8)0.0023 (8)
C140.0300 (9)0.0249 (9)0.0224 (9)0.0046 (7)0.0058 (7)0.0015 (7)
C150.033 (2)0.035 (3)0.034 (3)0.0014 (18)0.0024 (18)0.0051 (18)
C160.0342 (16)0.0261 (15)0.0284 (15)0.0032 (12)0.0009 (12)0.0054 (12)
C170.0290 (9)0.0252 (9)0.0244 (9)0.0002 (7)0.0063 (7)0.0010 (7)
C190.027 (3)0.021 (2)0.032 (3)0.004 (2)0.0073 (19)0.005 (2)
C200.044 (3)0.030 (3)0.030 (2)0.0030 (17)0.0086 (18)0.0053 (18)
C210.0427 (19)0.0276 (17)0.043 (2)0.0058 (15)0.0173 (17)0.0045 (15)
C220.046 (2)0.0344 (17)0.0329 (17)0.0167 (15)0.0121 (15)0.0056 (14)
C14A0.0300 (9)0.0249 (9)0.0224 (9)0.0046 (7)0.0058 (7)0.0015 (7)
C15A0.045 (5)0.024 (4)0.021 (3)0.006 (3)0.012 (3)0.008 (3)
C16A0.027 (3)0.028 (3)0.027 (3)0.008 (2)0.006 (2)0.007 (2)
C17A0.0290 (9)0.0252 (9)0.0244 (9)0.0002 (7)0.0063 (7)0.0010 (7)
C19A0.019 (5)0.025 (4)0.026 (5)0.007 (4)0.005 (3)0.007 (4)
C20A0.055 (6)0.048 (6)0.054 (6)0.000 (4)0.019 (4)0.008 (4)
C21A0.029 (3)0.042 (3)0.033 (3)0.002 (2)0.005 (2)0.013 (3)
C22A0.028 (3)0.021 (3)0.033 (3)0.002 (2)0.005 (2)0.000 (2)
N10.0542 (12)0.0386 (10)0.0670 (14)0.0029 (9)0.0189 (10)0.0085 (9)
N20.0453 (10)0.0389 (10)0.0436 (10)0.0028 (8)0.0171 (8)0.0011 (8)
N30.0437 (10)0.0424 (10)0.0410 (10)0.0040 (8)0.0160 (8)0.0002 (8)
N40.0310 (9)0.0449 (10)0.0428 (10)0.0070 (7)0.0110 (7)0.0076 (8)
C10.0331 (10)0.0315 (10)0.0485 (12)0.0037 (8)0.0072 (9)0.0023 (9)
C20.0478 (13)0.0380 (12)0.0519 (13)0.0025 (10)0.0115 (10)0.0072 (10)
C30.0450 (13)0.0367 (12)0.0760 (17)0.0091 (10)0.0127 (12)0.0019 (11)
C40.0423 (12)0.0363 (11)0.0531 (13)0.0022 (9)0.0066 (10)0.0006 (10)
C50.0304 (10)0.0279 (10)0.0502 (12)0.0070 (8)0.0103 (9)0.0032 (9)
C60.0383 (11)0.0360 (11)0.0426 (11)0.0064 (9)0.0097 (9)0.0012 (9)
C70.0395 (11)0.0361 (11)0.0352 (10)0.0050 (9)0.0106 (9)0.0012 (8)
C80.0290 (9)0.0294 (10)0.0366 (10)0.0087 (8)0.0090 (8)0.0012 (8)
C90.0380 (11)0.0514 (13)0.0335 (11)0.0067 (9)0.0040 (9)0.0012 (9)
C100.0415 (12)0.0656 (15)0.0313 (11)0.0019 (11)0.0046 (9)0.0074 (10)
C110.0271 (10)0.0372 (11)0.0510 (13)0.0049 (8)0.0072 (9)0.0018 (9)
C120.0326 (10)0.0424 (11)0.0329 (10)0.0071 (9)0.0054 (8)0.0004 (9)
N50.0327 (8)0.0291 (8)0.0337 (8)0.0026 (6)0.0119 (7)0.0003 (7)
N60.0294 (8)0.0306 (8)0.0314 (8)0.0005 (6)0.0111 (6)0.0061 (6)
C230.0288 (10)0.0328 (10)0.0315 (10)0.0055 (8)0.0047 (8)0.0025 (8)
C240.0357 (10)0.0346 (10)0.0282 (10)0.0032 (8)0.0053 (8)0.0018 (8)
C250.0263 (9)0.0369 (11)0.0403 (11)0.0055 (8)0.0051 (8)0.0031 (9)
C260.0295 (10)0.0371 (11)0.0329 (10)0.0022 (8)0.0028 (8)0.0049 (8)
C270.0286 (9)0.0236 (9)0.0293 (9)0.0008 (7)0.0089 (7)0.0000 (7)
C280.0273 (10)0.0311 (10)0.0280 (9)0.0006 (8)0.0055 (7)0.0018 (8)
Geometric parameters (Å, º) top
O1—C131.320 (2)C22A—H22E0.9800
O1—H1C1.01 (3)C22A—H22F0.9800
O2—C131.214 (2)N1—C31.333 (3)
O3—C181.320 (2)N1—C21.333 (3)
O3—H3C0.98 (3)N2—C61.274 (2)
O4—C181.216 (2)N2—N31.410 (2)
C13—C141.516 (2)N3—C71.272 (2)
C18—C171.510 (2)N4—C111.330 (3)
C14—C151.526 (5)N4—C101.334 (3)
C14—C201.560 (5)C1—C21.375 (3)
C14—C191.571 (7)C1—C51.389 (3)
C15—C161.566 (5)C1—H10.9500
C15—H15A0.9900C2—H20.9500
C15—H15B0.9900C3—C41.379 (3)
C16—C171.551 (3)C3—H30.9500
C16—H16A0.9900C4—C51.385 (3)
C16—H16B0.9900C4—H40.9500
C17—C191.533 (7)C5—C61.469 (3)
C17—H171.0000C6—H60.9500
C19—C221.535 (6)C7—C81.465 (3)
C19—C211.538 (5)C7—H70.9500
C20—H20A0.9800C8—C91.378 (3)
C20—H20B0.9800C8—C121.387 (3)
C20—H20C0.9800C9—C101.375 (3)
C21—H21A0.9800C9—H90.9500
C21—H21B0.9800C10—H100.9500
C21—H21C0.9800C11—C121.377 (3)
C22—H22A0.9800C11—H110.9500
C22—H22B0.9800C12—H120.9500
C22—H22C0.9800N5—C251.332 (2)
C15A—C16A1.532 (8)N5—C241.339 (2)
C15A—H15C0.9900N6—C281.272 (2)
C15A—H15D0.9900N6—N6i1.420 (3)
C16A—H16C0.9900C23—C241.377 (2)
C16A—H16D0.9900C23—C271.388 (2)
C19A—C22A1.510 (12)C23—H230.9500
C19A—C21A1.519 (8)C24—H240.9500
C20A—H20D0.9800C25—C261.376 (3)
C20A—H20E0.9800C25—H250.9500
C20A—H20F0.9800C26—C271.390 (2)
C21A—H21D0.9800C26—H260.9500
C21A—H21E0.9800C27—C281.471 (2)
C21A—H21F0.9800C28—H280.9500
C22A—H22D0.9800
C13—O1—H1C108.1 (15)C3—N1—C2116.09 (19)
C18—O3—H3C112.3 (15)C6—N2—N3112.42 (17)
O2—C13—O1122.64 (17)C7—N3—N2111.06 (17)
O2—C13—C14122.79 (17)C11—N4—C10117.10 (17)
O1—C13—C14114.56 (15)C2—C1—C5118.80 (19)
O4—C18—O3122.85 (17)C2—C1—H1120.6
O4—C18—C17123.90 (17)C5—C1—H1120.6
O3—C18—C17113.24 (15)N1—C2—C1124.4 (2)
C13—C14—C15119.9 (2)N1—C2—H2117.8
C13—C14—C20105.2 (2)C1—C2—H2117.8
C15—C14—C20108.6 (3)N1—C3—C4124.1 (2)
C13—C14—C19110.1 (3)N1—C3—H3118.0
C15—C14—C19102.5 (3)C4—C3—H3118.0
C20—C14—C19110.5 (3)C3—C4—C5119.0 (2)
C14—C15—C16106.9 (3)C3—C4—H4120.5
C14—C15—H15A110.4C5—C4—H4120.5
C16—C15—H15A110.4C4—C5—C1117.57 (19)
C14—C15—H15B110.4C4—C5—C6120.75 (19)
C16—C15—H15B110.4C1—C5—C6121.67 (18)
H15A—C15—H15B108.6N2—C6—C5119.85 (19)
C17—C16—C15104.3 (2)N2—C6—H6120.1
C17—C16—H16A110.9C5—C6—H6120.1
C15—C16—H16A110.9N3—C7—C8121.15 (18)
C17—C16—H16B110.9N3—C7—H7119.4
C15—C16—H16B110.9C8—C7—H7119.4
H16A—C16—H16B108.9C9—C8—C12117.65 (18)
C18—C17—C19114.4 (3)C9—C8—C7122.62 (18)
C18—C17—C16116.62 (16)C12—C8—C7119.72 (17)
C19—C17—C16105.1 (2)C10—C9—C8119.20 (19)
C18—C17—H17106.7C10—C9—H9120.4
C19—C17—H17106.7C8—C9—H9120.4
C16—C17—H17106.7N4—C10—C9123.55 (19)
C17—C19—C22113.2 (4)N4—C10—H10118.2
C17—C19—C21110.5 (4)C9—C10—H10118.2
C22—C19—C21108.0 (5)N4—C11—C12123.27 (19)
C17—C19—C14101.0 (4)N4—C11—H11118.4
C22—C19—C14114.1 (4)C12—C11—H11118.4
C21—C19—C14109.9 (3)C11—C12—C8119.23 (18)
C16A—C15A—H15C110.0C11—C12—H12120.4
C16A—C15A—H15D110.0C8—C12—H12120.4
H15C—C15A—H15D108.4C25—N5—C24117.35 (15)
C15A—C16A—H16C110.9C28—N6—N6i110.92 (17)
C15A—C16A—H16D110.9C24—C23—C27118.90 (16)
H16C—C16A—H16D108.9C24—C23—H23120.6
C22A—C19A—C21A111.2 (8)C27—C23—H23120.6
H20D—C20A—H20E109.5N5—C24—C23123.43 (17)
H20D—C20A—H20F109.5N5—C24—H24118.3
H20E—C20A—H20F109.5C23—C24—H24118.3
C19A—C21A—H21D109.5N5—C25—C26123.29 (17)
C19A—C21A—H21E109.5N5—C25—H25118.4
H21D—C21A—H21E109.5C26—C25—H25118.4
C19A—C21A—H21F109.5C25—C26—C27119.21 (17)
H21D—C21A—H21F109.5C25—C26—H26120.4
H21E—C21A—H21F109.5C27—C26—H26120.4
C19A—C22A—H22D109.5C23—C27—C26117.82 (16)
C19A—C22A—H22E109.5C23—C27—C28123.70 (16)
H22D—C22A—H22E109.5C26—C27—C28118.48 (16)
C19A—C22A—H22F109.5N6—C28—C27121.89 (16)
H22D—C22A—H22F109.5N6—C28—H28119.1
H22E—C22A—H22F109.5C27—C28—H28119.1
O2—C13—C14—C15157.6 (3)C5—C1—C2—N10.3 (3)
O1—C13—C14—C1523.0 (3)C2—N1—C3—C40.6 (3)
O2—C13—C14—C2035.2 (3)N1—C3—C4—C50.5 (3)
O1—C13—C14—C20145.5 (2)C3—C4—C5—C11.4 (3)
O2—C13—C14—C1983.9 (3)C3—C4—C5—C6177.85 (18)
O1—C13—C14—C1995.4 (2)C2—C1—C5—C41.3 (3)
C13—C14—C15—C16152.0 (2)C2—C1—C5—C6177.92 (18)
C20—C14—C15—C1687.2 (3)N3—N2—C6—C5179.67 (16)
C19—C14—C15—C1629.8 (4)C4—C5—C6—N2173.99 (18)
C14—C15—C16—C174.5 (4)C1—C5—C6—N25.2 (3)
O4—C18—C17—C19108.7 (3)N2—N3—C7—C8178.08 (16)
O3—C18—C17—C1972.3 (3)N3—C7—C8—C95.9 (3)
O4—C18—C17—C1614.5 (3)N3—C7—C8—C12172.68 (18)
O3—C18—C17—C16164.55 (17)C12—C8—C9—C100.7 (3)
C15—C16—C17—C18151.4 (3)C7—C8—C9—C10177.89 (19)
C15—C16—C17—C1923.5 (4)C11—N4—C10—C90.6 (3)
C18—C17—C19—C2266.8 (4)C8—C9—C10—N40.2 (3)
C16—C17—C19—C22164.0 (3)C10—N4—C11—C120.7 (3)
C18—C17—C19—C2154.5 (4)N4—C11—C12—C80.2 (3)
C16—C17—C19—C2174.7 (4)C9—C8—C12—C110.6 (3)
C18—C17—C19—C14170.80 (19)C7—C8—C12—C11178.07 (17)
C16—C17—C19—C1441.6 (3)C25—N5—C24—C230.9 (3)
C13—C14—C19—C17172.45 (18)C27—C23—C24—N50.4 (3)
C15—C14—C19—C1743.8 (3)C24—N5—C25—C260.6 (3)
C20—C14—C19—C1771.8 (3)N5—C25—C26—C270.2 (3)
C13—C14—C19—C2265.8 (4)C24—C23—C27—C260.3 (3)
C15—C14—C19—C22165.6 (4)C24—C23—C27—C28179.98 (17)
C20—C14—C19—C2250.0 (5)C25—C26—C27—C230.6 (3)
C13—C14—C19—C2155.7 (4)C25—C26—C27—C28179.67 (17)
C15—C14—C19—C2173.0 (5)N6i—N6—C28—C27179.13 (17)
C20—C14—C19—C21171.5 (3)C23—C27—C28—N62.8 (3)
C6—N2—N3—C7171.31 (17)C26—C27—C28—N6177.52 (17)
C3—N1—C2—C10.6 (3)
Symmetry code: (i) x+2, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1C···N4ii1.01 (3)1.65 (3)2.649 (2)170 (2)
O3—H3C···N50.98 (3)1.71 (3)2.6866 (19)176 (2)
Symmetry code: (ii) x3/2, y+3/2, z+1/2.

Experimental details

(CCP11)(CCP32)(ccr32)
Crystal data
Chemical formulaC12H10N4·C10H16O43(C12H10N4)·2(C10H16O4)3(C12H10N4)·2(C10H16O4)
Mr410.471031.181031.18
Crystal system, space groupOrthorhombic, P212121Monoclinic, P21Monoclinic, P21/n
Temperature (K)150110150
a, b, c (Å)7.2598 (11), 10.2744 (15), 27.997 (4)9.9568 (17), 12.914 (2), 20.203 (4)9.9407 (10), 12.9624 (13), 20.247 (2)
α, β, γ (°)90, 90, 9090, 95.734 (3), 9090, 95.928 (2), 90
V3)2088.3 (5)2584.7 (8)2595.0 (4)
Z422
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.090.090.09
Crystal size (mm)0.23 × 0.11 × 0.090.68 × 0.48 × 0.100.23 × 0.11 × 0.04
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Bruker SMART APEX CCD
diffractometer
Bruker SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
SADABS (Bruker, 2008)
Multi-scan
SADABS (Bruker, 2008)
Multi-scan
SADABS (Bruker, 2008)
Tmin, Tmax0.979, 0.9920.941, 0.9910.979, 0.996
No. of measured, independent and
observed [I > 2σ(I)] reflections
12500, 4834, 4686 12491, 9631, 8918 12644, 4541, 3787
Rint0.0260.0290.027
(sin θ/λ)max1)0.6600.6390.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.109, 1.13 0.071, 0.178, 1.11 0.049, 0.117, 1.12
No. of reflections483496314541
No. of parameters282695412
No. of restraints010
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH-atom parameters constrainedH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.34, 0.250.39, 0.290.19, 0.18

Computer programs: SMART (Bruker, 2008), SMART, SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), SHELXL97.

Hydrogen-bond geometry (Å, º) for (ccp11) top
D—H···AD—HH···AD···AD—H···A
O1—H1C···N4i0.85 (3)1.86 (3)2.699 (2)169 (3)
O3—H3C···N1ii0.85 (3)1.84 (3)2.675 (2)167 (3)
Symmetry codes: (i) x+2, y1/2, z+1/2; (ii) x+1/2, y+3/2, z.
Hydrogen-bond geometry (Å, º) for (ccp32) top
D—H···AD—HH···AD···AD—H···A
O1—H1C···N5i0.821.882.694 (4)176
O4—H4C···N40.821.832.639 (4)171
O6—H6C···N12ii0.821.832.641 (4)169
O7—H7C···N8iii0.821.892.702 (4)172
Symmetry codes: (i) x+2, y+1/2, z+1; (ii) x+1, y, z; (iii) x, y1/2, z+2.
Hydrogen-bond geometry (Å, º) for (ccr32) top
D—H···AD—HH···AD···AD—H···A
O1—H1C···N4i1.01 (3)1.65 (3)2.649 (2)170 (2)
O3—H3C···N50.98 (3)1.71 (3)2.6866 (19)176 (2)
Symmetry code: (i) x3/2, y+3/2, z+1/2.
 

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