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Pharmaceutical cocrystals are crystalline solids formed by an active pharmaceutical ingredient and a cocrystal former. The cocrystals 2,6-di­amino­pyridine (DAP)–piracetam [PIR; systematic name: 2-(2-oxopyrrolidin-1-yl)acetamide] (1/1), C5H7N3·C6H10N2O2, (I), and 2,6-di­amino­pyridine–theophylline (TEO; systematic name: 1,3-dimethyl-7H-purine-2,6-dione) (1/1), C5H7N3·C7H8N4O2, (II), were prepared by the solvent-assisted grinding method and were characterized by IR spectroscopy and powder X-ray diffraction. Cocrystal (I) crystallized in the ortho­rhom­bic space group Pbca and showed a 1:1 stoichiometry. The DAP and PIR molecules are linked by an N—H...O hydrogen-bond inter­action. Self-assembly of PIR mol­ecules forms a sheet of C(4) and C(7) chains. Cocrystal (II) crystallized in the monoclinic P21/c space group and also showed a 1:1 stoichiometry. The DAP and TEO molecules are connected by N—H...N and N—H...O hydrogen bonds, forming an R22(9) heterosynthon. A bidimensional supra­molecular array is formed by inter­linked DAP–TEO tetra­mers, producing a two-dimensional sheet.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961701230X/fn3239sup1.cif
Contains datablocks global, nemvucol73_0ma_a, monop21c_a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961701230X/fn3239nemvucol73_0ma_asup2.hkl
Contains datablock nemvucol73_0ma_a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961701230X/fn3239monop21c_asup3.hkl
Contains datablock monop21c_a

CCDC references: 1570704; 1570703

Computing details top

For both structures, data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SORTAV (Blessing, 1995); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

2,6-Diaminopyridine–2-(2-oxopyrrolidin-1-yl)acetamide (1/1) (nemvucol73_0ma_a) top
Crystal data top
C5H7N3·C6H10N2O2F(000) = 1072
Mr = 251.3Dx = 1.324 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 8544 reflections
a = 12.5854 (10) Åθ = 2.6–25.7°
b = 10.0901 (7) ŵ = 0.10 mm1
c = 19.8568 (16) ÅT = 293 K
V = 2521.6 (3) Å3Block, brown
Z = 80.3 × 0.2 × 0.1 mm
Data collection top
Bruker APEXII
diffractometer
2112 independent reflections
Radiation source: sealed x-ray tube1916 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
φ or ω oscillation scansθmax = 24.7°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
h = 1414
Tmin = 0.596, Tmax = 0.745k = 1111
9412 measured reflectionsl = 2322
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.136 w = 1/[σ2(Fo2) + (0.0372P)2 + 1.9621P]
where P = (Fo2 + 2Fc2)/3
S = 1.19(Δ/σ)max < 0.001
2112 reflectionsΔρmax = 0.23 e Å3
188 parametersΔρmin = 0.23 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.075 (4)
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C20.15470 (18)0.1293 (2)0.38814 (11)0.0408 (6)
C30.2301 (2)0.2293 (3)0.38717 (14)0.0521 (7)
H30.26580.25140.34770.063*
C40.2505 (2)0.2951 (3)0.44659 (14)0.0563 (7)
H40.30080.36260.44750.068*
C50.1969 (2)0.2617 (3)0.50482 (14)0.0514 (6)
H50.21010.30610.5450.062*
C60.12310 (19)0.1604 (2)0.50179 (12)0.0440 (6)
C120.49435 (16)0.3921 (2)0.19766 (11)0.0388 (5)
C130.5447 (2)0.5128 (3)0.16806 (13)0.0525 (7)
H13A0.62130.50970.17330.063*
H13B0.51810.59230.18980.063*
C140.5144 (2)0.5111 (3)0.09418 (14)0.0621 (8)
H14A0.48430.59570.0810.074*
H14B0.57630.49370.06650.074*
C150.4337 (2)0.4022 (2)0.08593 (12)0.0486 (6)
H15A0.36420.43850.07580.058*
H15B0.45420.34220.05010.058*
C160.38073 (18)0.2096 (2)0.16114 (12)0.0392 (6)
H16A0.42140.15960.19390.047*
H16B0.3830.16070.11910.047*
C170.26679 (17)0.2141 (2)0.18463 (10)0.0333 (5)
O120.50567 (13)0.34866 (18)0.25556 (8)0.0515 (5)
O170.21837 (14)0.10905 (16)0.19204 (9)0.0523 (5)
N10.10113 (15)0.09509 (18)0.44420 (9)0.0408 (5)
N20.1316 (2)0.0578 (3)0.33194 (12)0.0593 (7)
N60.0664 (3)0.1216 (3)0.55693 (13)0.0751 (9)
N110.43314 (14)0.33441 (18)0.15079 (9)0.0359 (5)
N180.22281 (17)0.3300 (2)0.19661 (10)0.0390 (5)
H2A0.157 (2)0.086 (3)0.2952 (15)0.056 (8)*
H2B0.087 (2)0.004 (3)0.3335 (12)0.041 (7)*
H6A0.019 (2)0.055 (3)0.5551 (14)0.062 (8)*
H6B0.080 (3)0.157 (3)0.5916 (18)0.074 (10)*
H18A0.156 (2)0.334 (3)0.2109 (13)0.047 (7)*
H18B0.256 (2)0.404 (3)0.1909 (12)0.043 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0407 (12)0.0380 (12)0.0435 (13)0.0055 (10)0.0004 (10)0.0048 (10)
C30.0521 (15)0.0476 (14)0.0565 (15)0.0018 (12)0.0073 (12)0.0095 (12)
C40.0537 (15)0.0425 (14)0.0727 (18)0.0158 (12)0.0074 (13)0.0090 (13)
C50.0571 (15)0.0458 (14)0.0511 (14)0.0073 (12)0.0139 (12)0.0016 (11)
C60.0484 (13)0.0417 (13)0.0419 (13)0.0025 (10)0.0083 (10)0.0040 (10)
C120.0289 (11)0.0468 (13)0.0407 (13)0.0062 (9)0.0017 (9)0.0038 (10)
C130.0468 (14)0.0510 (15)0.0598 (16)0.0075 (12)0.0021 (12)0.0036 (12)
C140.0673 (18)0.0609 (17)0.0580 (17)0.0095 (14)0.0066 (14)0.0137 (13)
C150.0603 (15)0.0509 (14)0.0346 (12)0.0009 (12)0.0017 (11)0.0045 (10)
C160.0418 (12)0.0333 (11)0.0425 (12)0.0049 (9)0.0013 (10)0.0005 (9)
C170.0421 (12)0.0299 (11)0.0278 (10)0.0017 (9)0.0001 (9)0.0007 (8)
O120.0499 (10)0.0661 (11)0.0385 (9)0.0027 (8)0.0093 (7)0.0042 (8)
O170.0598 (11)0.0326 (9)0.0645 (11)0.0086 (8)0.0149 (8)0.0009 (8)
N10.0434 (10)0.0389 (10)0.0402 (11)0.0040 (8)0.0027 (8)0.0032 (8)
N20.0746 (17)0.0612 (15)0.0422 (13)0.0162 (13)0.0096 (12)0.0024 (11)
N60.097 (2)0.091 (2)0.0377 (13)0.0467 (17)0.0010 (13)0.0065 (13)
N110.0359 (10)0.0388 (10)0.0329 (10)0.0011 (8)0.0005 (7)0.0019 (8)
N180.0379 (11)0.0312 (11)0.0478 (12)0.0012 (9)0.0086 (8)0.0001 (8)
Geometric parameters (Å, º) top
C2—N11.346 (3)C14—H14A0.97
C2—N21.360 (3)C14—H14B0.97
C2—C31.386 (3)C15—N111.459 (3)
C3—C41.378 (4)C15—H15A0.97
C3—H30.93C15—H15B0.97
C4—C51.381 (4)C16—N111.436 (3)
C4—H40.93C16—C171.509 (3)
C5—C61.383 (3)C16—H16A0.97
C5—H50.93C16—H16B0.97
C6—N11.348 (3)C17—O171.232 (3)
C6—N61.364 (3)C17—N181.315 (3)
C12—O121.239 (3)N2—H2A0.85 (3)
C12—N111.341 (3)N2—H2B0.84 (3)
C12—C131.493 (3)N6—H6A0.90 (3)
C13—C141.516 (4)N6—H6B0.79 (4)
C13—H13A0.97N18—H18A0.88 (3)
C13—H13B0.97N18—H18B0.87 (3)
C14—C151.505 (4)
N1—C2—N2115.8 (2)H14A—C14—H14B108.6
N1—C2—C3122.8 (2)N11—C15—C14104.4 (2)
N2—C2—C3121.4 (2)N11—C15—H15A110.9
C4—C3—C2117.8 (2)C14—C15—H15A110.9
C4—C3—H3121.1N11—C15—H15B110.9
C2—C3—H3121.1C14—C15—H15B110.9
C3—C4—C5120.6 (2)H15A—C15—H15B108.9
C3—C4—H4119.7N11—C16—C17117.03 (17)
C5—C4—H4119.7N11—C16—H16A108
C4—C5—C6118.2 (2)C17—C16—H16A108
C4—C5—H5120.9N11—C16—H16B108
C6—C5—H5120.9C17—C16—H16B108
N1—C6—N6115.7 (2)H16A—C16—H16B107.3
N1—C6—C5122.4 (2)O17—C17—N18122.4 (2)
N6—C6—C5121.9 (2)O17—C17—C16118.77 (19)
O12—C12—N11123.8 (2)N18—C17—C16118.86 (19)
O12—C12—C13127.2 (2)C2—N1—C6118.3 (2)
N11—C12—C13108.9 (2)C2—N2—H2A116.8 (19)
C12—C13—C14105.3 (2)C2—N2—H2B120.3 (17)
C12—C13—H13A110.7H2A—N2—H2B122 (3)
C14—C13—H13A110.7C6—N6—H6A121.9 (19)
C12—C13—H13B110.7C6—N6—H6B117 (2)
C14—C13—H13B110.7H6A—N6—H6B121 (3)
H13A—C13—H13B108.8C12—N11—C16123.03 (18)
C15—C14—C13106.5 (2)C12—N11—C15113.98 (19)
C15—C14—H14A110.4C16—N11—C15122.68 (18)
C13—C14—H14A110.4C17—N18—H18A119.8 (17)
C15—C14—H14B110.4C17—N18—H18B122.6 (17)
C13—C14—H14B110.4H18A—N18—H18B118 (2)
N1—C2—C3—C40.3 (4)N2—C2—N1—C6178.2 (2)
N2—C2—C3—C4178.6 (2)C3—C2—N1—C60.8 (3)
C2—C3—C4—C50.1 (4)N6—C6—N1—C2180.0 (2)
C3—C4—C5—C60.4 (4)C5—C6—N1—C21.1 (3)
C4—C5—C6—N10.9 (4)O12—C12—N11—C165.2 (3)
C4—C5—C6—N6179.7 (3)C13—C12—N11—C16174.40 (19)
O12—C12—C13—C14173.6 (2)O12—C12—N11—C15178.9 (2)
N11—C12—C13—C146.0 (3)C13—C12—N11—C150.7 (3)
C12—C13—C14—C158.8 (3)C17—C16—N11—C1295.4 (2)
C13—C14—C15—N118.4 (3)C17—C16—N11—C1591.4 (2)
N11—C16—C17—O17177.80 (19)C14—C15—N11—C125.0 (3)
N11—C16—C17—N182.3 (3)C14—C15—N11—C16168.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O170.85 (3)2.20 (3)3.029 (3)166 (3)
N2—H2B···O12i0.84 (3)2.44 (3)3.121 (3)138 (2)
N6—H6A···N1ii0.90 (3)2.14 (3)3.038 (4)176 (3)
N18—H18A···O12iii0.89 (3)2.01 (3)2.899 (3)178 (3)
N18—H18B···N110.86 (3)2.47 (3)2.799 (3)104 (2)
N18—H18B···O17iv0.86 (3)2.09 (3)2.913 (3)158 (2)
Symmetry codes: (i) x+1/2, y1/2, z; (ii) x, y, z+1; (iii) x1/2, y, z+1/2; (iv) x+1/2, y+1/2, z.
2,6-Diaminopyridine–1,3-dimethyl-7H-purine-2,6-dione (1/1) (monop21c_a) top
Crystal data top
C5H7N3·C7H8N4O2F(000) = 608
Mr = 289.31Dx = 1.441 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9001 reflections
a = 9.5439 (3) Åθ = 2.6–25.8°
b = 15.6588 (5) ŵ = 0.11 mm1
c = 9.4887 (3) ÅT = 293 K
β = 109.927 (1)°Prism, grey
V = 1333.15 (7) Å30.3 × 0.2 × 0.1 mm
Z = 4
Data collection top
Bruker APEX-II
diffractometer
2564 independent reflections
Radiation source: sealed x-ray tube2381 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
φ or ω oscillation scansθmax = 25.8°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
h = 1111
Tmin = 0.704, Tmax = 0.745k = 1919
30803 measured reflectionsl = 1111
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0555P)2 + 0.4344P]
where P = (Fo2 + 2Fc2)/3
2564 reflections(Δ/σ)max = 0.001
216 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.18 e Å3
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C20.21247 (15)0.81387 (9)0.54567 (15)0.0368 (3)
C30.10890 (18)0.87773 (10)0.54065 (18)0.0467 (4)
H30.12150.9330.51110.056*
C40.01177 (18)0.85673 (11)0.5805 (2)0.0546 (4)
H40.08220.89830.57780.066*
C50.03043 (18)0.77507 (11)0.6245 (2)0.0523 (4)
H50.11180.76090.65270.063*
C60.07612 (15)0.71453 (9)0.62537 (15)0.0382 (3)
C110.72267 (17)0.63726 (11)0.3094 (2)0.0511 (4)
H11A0.80310.59840.31870.077*
H11B0.7530.67810.38950.077*
H11C0.69670.66650.2150.077*
C120.56570 (15)0.51097 (9)0.24475 (15)0.0366 (3)
C130.41450 (19)0.38156 (10)0.1791 (2)0.0523 (4)
H13A0.39560.38530.07320.079*
H13B0.32960.35690.19620.079*
H13C0.50040.34630.22460.079*
C140.34892 (14)0.50266 (8)0.31251 (14)0.0334 (3)
C150.37949 (14)0.58001 (8)0.38233 (14)0.0333 (3)
C160.50554 (14)0.62997 (8)0.38947 (15)0.0351 (3)
C180.17543 (16)0.52711 (9)0.39562 (17)0.0416 (3)
N10.19525 (12)0.73342 (7)0.58614 (12)0.0358 (3)
N20.33778 (15)0.83020 (9)0.51273 (16)0.0481 (3)
N60.06279 (16)0.63045 (9)0.65948 (16)0.0463 (3)
N110.59354 (12)0.58973 (7)0.31676 (13)0.0364 (3)
N130.44179 (12)0.46717 (7)0.24499 (13)0.0371 (3)
N170.26514 (12)0.59486 (7)0.43666 (13)0.0375 (3)
N190.22118 (13)0.46826 (7)0.32006 (14)0.0403 (3)
O120.65115 (12)0.48205 (7)0.18507 (13)0.0497 (3)
O160.54008 (12)0.69939 (6)0.45042 (13)0.0491 (3)
H2A0.341 (2)0.8797 (13)0.462 (2)0.060 (5)*
H2B0.392 (2)0.7878 (13)0.503 (2)0.061 (5)*
H6A0.148 (2)0.5994 (12)0.700 (2)0.060 (5)*
H6B0.002 (2)0.6222 (12)0.698 (2)0.061 (5)*
H170.249 (2)0.6465 (12)0.488 (2)0.056 (5)*
H180.0839 (19)0.5229 (11)0.4224 (19)0.051 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0393 (7)0.0370 (7)0.0349 (6)0.0027 (5)0.0139 (5)0.0032 (5)
C30.0539 (9)0.0366 (7)0.0513 (8)0.0035 (6)0.0199 (7)0.0020 (6)
C40.0481 (9)0.0485 (9)0.0704 (11)0.0106 (7)0.0244 (8)0.0101 (8)
C50.0428 (8)0.0535 (9)0.0710 (11)0.0003 (7)0.0329 (8)0.0113 (8)
C60.0369 (7)0.0421 (7)0.0405 (7)0.0044 (6)0.0193 (6)0.0078 (6)
C110.0424 (8)0.0516 (9)0.0699 (10)0.0094 (7)0.0328 (8)0.0061 (8)
C120.0359 (7)0.0371 (7)0.0406 (7)0.0047 (5)0.0178 (6)0.0015 (5)
C130.0563 (9)0.0411 (8)0.0677 (10)0.0049 (7)0.0315 (8)0.0165 (7)
C140.0342 (6)0.0320 (6)0.0371 (7)0.0024 (5)0.0163 (5)0.0029 (5)
C150.0334 (6)0.0326 (6)0.0384 (7)0.0027 (5)0.0181 (5)0.0012 (5)
C160.0348 (7)0.0328 (7)0.0409 (7)0.0023 (5)0.0170 (5)0.0012 (5)
C180.0396 (7)0.0393 (7)0.0543 (8)0.0030 (6)0.0270 (6)0.0003 (6)
N10.0351 (6)0.0369 (6)0.0398 (6)0.0006 (4)0.0185 (5)0.0027 (5)
N20.0501 (8)0.0409 (7)0.0629 (8)0.0012 (6)0.0315 (6)0.0052 (6)
N60.0450 (7)0.0454 (7)0.0588 (8)0.0053 (6)0.0311 (7)0.0001 (6)
N110.0325 (6)0.0362 (6)0.0455 (6)0.0005 (4)0.0197 (5)0.0002 (5)
N130.0388 (6)0.0327 (6)0.0451 (6)0.0005 (4)0.0210 (5)0.0048 (5)
N170.0385 (6)0.0353 (6)0.0466 (6)0.0005 (5)0.0246 (5)0.0016 (5)
N190.0399 (6)0.0363 (6)0.0506 (7)0.0040 (5)0.0233 (5)0.0009 (5)
O120.0476 (6)0.0506 (6)0.0624 (7)0.0042 (5)0.0338 (5)0.0080 (5)
O160.0482 (6)0.0366 (6)0.0702 (7)0.0071 (4)0.0301 (5)0.0124 (5)
Geometric parameters (Å, º) top
C2—N11.3434 (18)C13—H13A0.96
C2—N21.3594 (18)C13—H13B0.96
C2—C31.395 (2)C13—H13C0.96
C3—C41.369 (2)C14—N191.3569 (16)
C3—H30.93C14—C151.3636 (18)
C4—C51.375 (2)C14—N131.3756 (16)
C4—H40.93C15—N171.3764 (16)
C5—C61.388 (2)C15—C161.4170 (18)
C5—H50.93C16—O161.2227 (17)
C6—N11.3444 (17)C16—N111.4048 (16)
C6—N61.372 (2)C18—N191.3294 (18)
C11—N111.4617 (17)C18—N171.3354 (18)
C11—H11A0.96C18—H180.992 (17)
C11—H11B0.96N2—H2A0.92 (2)
C11—H11C0.96N2—H2B0.86 (2)
C12—O121.2272 (16)N6—H6A0.91 (2)
C12—N131.3677 (17)N6—H6B0.83 (2)
C12—N111.3908 (18)N17—H170.982 (18)
C13—N131.4645 (18)
N1—C2—N2116.42 (13)N19—C14—C15111.98 (11)
N1—C2—C3121.84 (13)N19—C14—N13126.68 (12)
N2—C2—C3121.72 (14)C15—C14—N13121.33 (12)
C4—C3—C2118.12 (14)C14—C15—N17105.45 (11)
C4—C3—H3120.9C14—C15—C16123.45 (12)
C2—C3—H3120.9N17—C15—C16131.10 (12)
C3—C4—C5121.01 (14)O16—C16—N11121.41 (12)
C3—C4—H4119.5O16—C16—C15126.94 (12)
C5—C4—H4119.5N11—C16—C15111.64 (11)
C4—C5—C6117.81 (14)N19—C18—N17114.34 (12)
C4—C5—H5121.1N19—C18—H18124.9 (10)
C6—C5—H5121.1N17—C18—H18120.7 (10)
N1—C6—N6115.57 (12)C2—N1—C6118.87 (12)
N1—C6—C5122.34 (14)C2—N2—H2A118.1 (12)
N6—C6—C5122.02 (13)C2—N2—H2B118.8 (13)
N11—C11—H11A109.5H2A—N2—H2B117.7 (17)
N11—C11—H11B109.5C6—N6—H6A118.1 (12)
H11A—C11—H11B109.5C6—N6—H6B113.3 (14)
N11—C11—H11C109.5H6A—N6—H6B115.1 (18)
H11A—C11—H11C109.5C12—N11—C16126.36 (11)
H11B—C11—H11C109.5C12—N11—C11116.81 (11)
O12—C12—N13121.78 (13)C16—N11—C11116.75 (12)
O12—C12—N11120.54 (12)C12—N13—C14119.53 (11)
N13—C12—N11117.67 (11)C12—N13—C13119.10 (11)
N13—C13—H13A109.5C14—N13—C13121.31 (12)
N13—C13—H13B109.5C18—N17—C15105.54 (11)
H13A—C13—H13B109.5C18—N17—H17127.2 (11)
N13—C13—H13C109.5C15—N17—H17127.1 (11)
H13A—C13—H13C109.5C18—N19—C14102.68 (11)
H13B—C13—H13C109.5
N1—C2—C3—C40.9 (2)O12—C12—N11—C113.6 (2)
N2—C2—C3—C4177.74 (14)N13—C12—N11—C11177.30 (13)
C2—C3—C4—C50.1 (2)O16—C16—N11—C12179.63 (13)
C3—C4—C5—C60.7 (3)C15—C16—N11—C120.14 (19)
C4—C5—C6—N10.5 (2)O16—C16—N11—C113.8 (2)
C4—C5—C6—N6176.32 (15)C15—C16—N11—C11176.72 (12)
N19—C14—C15—N170.08 (15)O12—C12—N13—C14179.53 (13)
N13—C14—C15—N17179.70 (12)N11—C12—N13—C141.33 (19)
N19—C14—C15—C16179.33 (12)O12—C12—N13—C133.2 (2)
N13—C14—C15—C160.9 (2)N11—C12—N13—C13175.92 (13)
C14—C15—C16—O16179.67 (14)N19—C14—N13—C12178.80 (12)
N17—C15—C16—O161.1 (2)C15—C14—N13—C121.5 (2)
C14—C15—C16—N110.21 (19)N19—C14—N13—C134.0 (2)
N17—C15—C16—N11179.47 (13)C15—C14—N13—C13175.74 (13)
N2—C2—N1—C6177.52 (12)N19—C18—N17—C150.62 (17)
C3—C2—N1—C61.2 (2)C14—C15—N17—C180.40 (15)
N6—C6—N1—C2177.48 (12)C16—C15—N17—C18178.95 (14)
C5—C6—N1—C20.5 (2)N17—C18—N19—C140.56 (17)
O12—C12—N11—C16179.86 (13)C15—C14—N19—C180.27 (15)
N13—C12—N11—C160.7 (2)N13—C14—N19—C18179.96 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O12i0.92 (2)2.14 (2)3.0533 (18)170.8 (17)
N2—H2B···O160.87 (2)2.16 (2)3.0085 (18)168.6 (18)
N6—H6A···O12ii0.91 (2)2.251 (19)3.1603 (19)174.8 (17)
N6—H6B···N19iii0.83 (2)2.48 (2)3.183 (2)142.8 (16)
N17—H17···N10.98 (2)1.819 (19)2.7945 (16)171.3 (18)
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+1, y+1, z+1; (iii) x, y+1, z+1.
 

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