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Four new cocrystals of pyrimidin-2-amine and propane-1,3-di­carb­oxy­lic (glutaric) acid were crystallized from three different solvents (aceto­nitrile, methanol and a 50:50 wt% mixture of methanol and chloro­form) and their crystal structures determined. Two of the cocrystals, namely pyrimidin-2-amine-glutaric acid (1/1), C4H5N3·C6H8O4, (I) and (II), are polymorphs. The glutaric acid mol­ecule in (I) has a linear conformation, whereas it is twisted in (II). The pyrimidin-2-amine-glutaric acid (2/1) cocrystal, 2C4H5N3·C6H8O4, (III), contains glutaric acid in its linear form. Cocrystal-salt bis­(2-amino­pyrimidinium) glutarate-glutaric acid (1/2), 2C4H6N3+·C6H6O42-·2C6H8O4, (IV), was crystallized from the same solvent as cocrystal (II), supporting the idea of a cocrystal-salt continuum when both the neutral and ionic forms are present in appreciable concentrations in solution. The diversity of the packing motifs in (I)-(IV) is mainly caused by the conformational flexibility of glutaric acid, while the hydrogen-bond patterns show certain similarities in all four structures.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615004283/lg3157sup1.cif
Contains datablocks I, II, III, IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615004283/lg3157Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615004283/lg3157IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615004283/lg3157IIIsup4.hkl
Contains datablock III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615004283/lg3157IVsup5.hkl
Contains datablock IV

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615004283/lg3157Isup6.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615004283/lg3157IIsup7.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615004283/lg3157IIIsup8.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615004283/lg3157IVsup9.cml
Supplementary material

CCDC references: 1051730; 1051729; 1051728; 1051727

Computing details top

For all compounds, data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (I), (III), (IV); SUPERFLIP (Palatinus & Chapius, 2007) for (II). For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(I) Pyrimidin-2-amine–glutaric acid (1/1) top
Crystal data top
C4H5N3·C5H8O4Dx = 1.407 Mg m3
Mr = 227.22Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcmCell parameters from 2706 reflections
a = 4.1667 (4) Åθ = 3.2–30.9°
b = 12.6657 (11) ŵ = 0.11 mm1
c = 20.3238 (18) ÅT = 120 K
V = 1072.57 (17) Å3Prism, clear light colourless
Z = 40.44 × 0.36 × 0.14 mm
F(000) = 480
Data collection top
Bruker SMART CCD 6000 area detector
diffractometer
1525 independent reflections
Radiation source: sealed X-ray tube, sealed X-ray tube1208 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 5.6 pixels mm-1θmax = 29.5°, θmin = 2.0°
ω scansh = 55
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
k = 1717
Tmin = 0.428, Tmax = 1.000l = 2727
9365 measured reflections
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)] = 0.054Hydrogen site location: difference Fourier map
wR(F2) = 0.149All H-atom parameters refined
S = 1.06 w = 1/[σ2(Fo2) + (0.075P)2 + 0.7P]
where P = (Fo2 + 2Fc2)/3
1525 reflections(Δ/σ)max < 0.001
105 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.31 e Å3
Special details top

Experimental. Absorption correction: SADABS-2006/1 (Bruker,2006) was used for absorption correction. R(int) was 0.0378 before and 0.0274 after correction. The Ratio of minimum to maximum transmission is 0.4278. The λ/2 correction factor is 0.0015.

The data collection nominally covered a full sphere of reciprocal space by a combination of 3 sets of ω scans each set at different φ and/or 2θ angles and each scan (3 s exposure) covering -0.300° degrees in ω. The crystal to detector distance was 5.85 cm.

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
O10.0812 (3)0.45503 (8)0.42387 (5)0.0274 (3)
O20.2865 (3)0.30700 (9)0.38120 (5)0.0307 (3)
N10.0630 (5)0.37091 (15)0.25000.0289 (4)
N20.2000 (3)0.50020 (10)0.30879 (6)0.0236 (3)
C10.1154 (5)0.45857 (16)0.25000.0228 (4)
C20.3857 (4)0.58639 (11)0.30791 (7)0.0251 (3)
C30.4894 (6)0.63265 (16)0.25000.0267 (4)
C40.2530 (3)0.36731 (11)0.42703 (7)0.0215 (3)
C50.4034 (4)0.35156 (11)0.49387 (7)0.0221 (3)
C60.5961 (5)0.25000.50000.0226 (4)
H1A0.132 (6)0.3467 (18)0.2868 (11)0.042 (6)*
H10.012 (7)0.4621 (19)0.3836 (12)0.049 (6)*
H20.444 (5)0.6172 (15)0.3487 (10)0.027 (5)*
H30.620 (7)0.692 (2)0.25000.034 (7)*
H5A0.232 (4)0.3555 (14)0.5261 (9)0.023 (4)*
H5B0.539 (5)0.4150 (16)0.5018 (10)0.035 (5)*
H60.732 (5)0.2443 (16)0.4620 (10)0.030 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0352 (6)0.0241 (5)0.0228 (5)0.0080 (4)0.0021 (4)0.0005 (4)
O20.0436 (7)0.0247 (5)0.0238 (6)0.0070 (5)0.0012 (5)0.0022 (4)
N10.0393 (11)0.0262 (9)0.0212 (9)0.0084 (8)0.0000.000
N20.0267 (6)0.0214 (6)0.0226 (6)0.0005 (5)0.0007 (4)0.0004 (4)
C10.0245 (9)0.0209 (9)0.0230 (9)0.0016 (7)0.0000.000
C20.0275 (7)0.0219 (7)0.0258 (7)0.0006 (6)0.0015 (5)0.0025 (5)
C30.0286 (10)0.0215 (9)0.0300 (10)0.0031 (8)0.0000.000
C40.0240 (6)0.0183 (6)0.0222 (6)0.0007 (5)0.0023 (5)0.0021 (5)
C50.0249 (7)0.0185 (6)0.0229 (7)0.0007 (5)0.0000 (5)0.0003 (5)
C60.0223 (9)0.0196 (9)0.0260 (10)0.0000.0000.0022 (7)
Geometric parameters (Å, º) top
O1—C41.3234 (17)C2—H20.95 (2)
O1—H10.91 (3)C3—C2i1.3840 (19)
O2—C41.2127 (18)C3—H30.93 (3)
N1—C11.336 (3)C4—C51.509 (2)
N1—H1A0.86 (2)C5—C61.5216 (17)
N2—C11.3527 (15)C5—H5A0.970 (19)
N2—C21.3381 (19)C5—H5B0.99 (2)
C1—N2i1.3528 (15)C6—C5ii1.5216 (17)
C2—C31.3840 (19)C6—H60.96 (2)
C4—O1—H1110.9 (15)O1—C4—C5112.29 (12)
C1—N1—H1A118.9 (15)O2—C4—O1123.63 (13)
C2—N2—C1117.18 (13)O2—C4—C5124.08 (13)
N1—C1—N2117.96 (9)C4—C5—C6113.86 (11)
N1—C1—N2i117.96 (9)C4—C5—H5A107.1 (11)
N2—C1—N2i124.08 (18)C4—C5—H5B105.9 (12)
N2—C2—C3122.50 (14)C6—C5—H5A112.2 (11)
N2—C2—H2118.2 (12)C6—C5—H5B111.8 (12)
C3—C2—H2119.3 (12)H5A—C5—H5B105.4 (16)
C2i—C3—C2116.52 (19)C5—C6—C5ii116.29 (17)
C2—C3—H3121.74 (10)C5ii—C6—H6108.3 (12)
C2i—C3—H3121.74 (10)C5—C6—H6108.1 (12)
O1—C4—C5—C6178.52 (12)C2—N2—C1—N1178.29 (16)
O2—C4—C5—C61.9 (2)C2—N2—C1—N2i1.8 (3)
N2—C2—C3—C2i1.3 (3)C4—C5—C6—C5ii74.96 (10)
C1—N2—C2—C30.2 (2)
Symmetry codes: (i) x, y, z+1/2; (ii) x, y+1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O20.86 (2)2.08 (2)2.9381 (14)173 (2)
O1—H1···N20.91 (3)1.78 (3)2.6775 (17)170 (2)
(II) Pyrimidin-2-amine–glutaric acid (1/1) top
Crystal data top
C4H5N3·C5H8O4Z = 2
Mr = 227.22F(000) = 240
Triclinic, P1Dx = 1.437 Mg m3
a = 6.0184 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.4714 (5) ÅCell parameters from 5873 reflections
c = 12.0911 (7) Åθ = 2.8–30.9°
α = 84.371 (1)°µ = 0.11 mm1
β = 89.906 (1)°T = 120 K
γ = 76.094 (2)°Block, clear light colourless
V = 525.07 (6) Å30.56 × 0.3 × 0.24 mm
Data collection top
Bruker SMART CCD 6000 area-detector
diffractometer
2794 independent reflections
Radiation source: sealed X-ray tube, sealed X-ray tube2279 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 5.6 pixels mm-1θmax = 29.0°, θmin = 1.7°
ω scansh = 88
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
k = 1010
Tmin = 0.539, Tmax = 1.000l = 1616
12033 measured reflections
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: difference Fourier map
wR(F2) = 0.126All H-atom parameters refined
S = 1.04 w = 1/[σ2(Fo2) + (0.080P)2 + 0.090P]
where P = (Fo2 + 2Fc2)/3
2794 reflections(Δ/σ)max < 0.001
197 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.26 e Å3
Special details top

Experimental. Absorption correction: SADABS-2006/1 (Bruker,2006) was used for absorption correction. R(int) was 0.0600 before and 0.0237 after correction. The Ratio of minimum to maximum transmission is 0.5386. The λ/2 correction factor is 0.0015.

The data collection nominally covered a full sphere of reciprocal space by a combination of 6 sets of ω scans each set at different φ and/or 2θ angles and each scan (5 s exposure) covering -0.300° degrees in ω. The crystal to detector distance was 4.85 cm.

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
O10.46021 (15)0.32178 (13)0.61425 (6)0.0309 (2)
O20.64621 (15)0.17335 (12)0.47659 (6)0.0312 (2)
O30.13451 (14)0.23991 (12)0.11736 (6)0.0279 (2)
O40.21468 (15)0.42911 (12)0.11277 (7)0.0332 (2)
C210.47520 (19)0.26733 (15)0.51269 (8)0.0240 (2)
C220.24898 (18)0.33965 (16)0.45089 (8)0.0248 (2)
C230.24434 (18)0.30029 (15)0.33035 (8)0.0229 (2)
C240.00358 (19)0.38108 (15)0.28162 (8)0.0231 (2)
C250.03390 (19)0.35239 (15)0.16201 (8)0.0239 (2)
H10.587 (4)0.273 (3)0.6584 (19)0.071 (6)*
H30.086 (4)0.230 (3)0.0469 (19)0.064 (6)*
H22A0.136 (3)0.285 (2)0.4930 (13)0.034 (4)*
H22B0.201 (3)0.474 (2)0.4558 (13)0.035 (4)*
H23A0.350 (2)0.3549 (19)0.2902 (11)0.023 (3)*
H23B0.286 (2)0.170 (2)0.3265 (11)0.024 (3)*
H24A0.105 (2)0.3244 (19)0.3239 (12)0.028 (3)*
H24B0.046 (2)0.514 (2)0.2875 (12)0.026 (3)*
N10.67341 (18)0.32172 (15)0.90019 (8)0.0319 (2)
N21.05289 (16)0.16702 (13)0.91090 (7)0.0242 (2)
N30.83099 (17)0.18650 (13)0.74480 (7)0.0248 (2)
C10.85433 (19)0.22400 (15)0.85062 (8)0.0232 (2)
C21.2312 (2)0.06618 (17)0.86220 (9)0.0280 (2)
C31.2216 (2)0.01773 (17)0.75500 (9)0.0292 (2)
C41.0131 (2)0.08427 (16)0.69945 (9)0.0270 (2)
H1A0.547 (3)0.376 (2)0.8634 (15)0.047 (5)*
H1B0.700 (3)0.357 (2)0.9633 (15)0.041 (4)*
H21.377 (3)0.024 (2)0.9054 (14)0.042 (4)*
H40.999 (3)0.051 (2)0.6219 (14)0.039 (4)*
H3A1.347 (3)0.056 (2)0.7205 (14)0.039 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0322 (4)0.0432 (5)0.0151 (4)0.0021 (4)0.0052 (3)0.0096 (3)
O20.0294 (4)0.0422 (5)0.0197 (4)0.0017 (3)0.0034 (3)0.0094 (3)
O30.0276 (4)0.0387 (5)0.0163 (4)0.0038 (3)0.0043 (3)0.0082 (3)
O40.0349 (5)0.0363 (5)0.0231 (4)0.0039 (3)0.0124 (3)0.0087 (3)
C210.0294 (5)0.0296 (5)0.0145 (4)0.0091 (4)0.0027 (4)0.0040 (4)
C220.0244 (5)0.0349 (6)0.0154 (4)0.0065 (4)0.0021 (4)0.0060 (4)
C230.0239 (5)0.0305 (5)0.0151 (4)0.0070 (4)0.0030 (4)0.0047 (4)
C240.0256 (5)0.0274 (5)0.0164 (4)0.0052 (4)0.0033 (4)0.0057 (4)
C250.0284 (5)0.0259 (5)0.0176 (5)0.0071 (4)0.0046 (4)0.0026 (4)
N10.0319 (5)0.0391 (6)0.0208 (5)0.0027 (4)0.0087 (4)0.0111 (4)
N20.0273 (5)0.0291 (5)0.0170 (4)0.0074 (4)0.0042 (3)0.0041 (3)
N30.0340 (5)0.0258 (4)0.0150 (4)0.0076 (4)0.0055 (3)0.0031 (3)
C10.0303 (5)0.0236 (5)0.0161 (4)0.0071 (4)0.0050 (4)0.0026 (3)
C20.0265 (5)0.0355 (6)0.0233 (5)0.0090 (4)0.0026 (4)0.0056 (4)
C30.0299 (6)0.0360 (6)0.0232 (5)0.0087 (5)0.0040 (4)0.0082 (4)
C40.0376 (6)0.0287 (5)0.0176 (5)0.0128 (4)0.0008 (4)0.0046 (4)
Geometric parameters (Å, º) top
O1—C211.3273 (12)C24—H24A0.977 (14)
O1—H10.91 (3)C24—H24B0.975 (14)
O2—C211.2058 (14)N1—C11.3340 (15)
O3—C251.3049 (14)N1—H1A0.872 (19)
O3—H30.92 (2)N1—H1B0.860 (19)
O4—C251.2256 (13)N2—C11.3557 (13)
C21—C221.5081 (14)N2—C21.3274 (15)
C22—C231.5165 (14)N3—C11.3509 (13)
C22—H22A0.990 (15)N3—C41.3279 (15)
C22—H22B0.987 (16)C2—C31.3844 (15)
C23—C241.5244 (15)C2—H20.989 (17)
C23—H23A0.942 (13)C3—C41.3821 (16)
C23—H23B0.948 (14)C3—H3A0.947 (17)
C24—C251.5078 (13)C4—H41.002 (17)
C21—O1—H1114.4 (14)H24A—C24—H24B106.3 (12)
C25—O3—H3106.6 (14)O3—C25—C24115.72 (9)
O1—C21—C22110.07 (9)O4—C25—O3123.60 (9)
O2—C21—O1124.15 (10)O4—C25—C24120.66 (10)
O2—C21—C22125.77 (9)C1—N1—H1A121.7 (12)
C21—C22—C23116.16 (9)C1—N1—H1B116.1 (11)
C21—C22—H22A106.6 (9)H1A—N1—H1B119.6 (17)
C21—C22—H22B107.9 (9)C2—N2—C1117.05 (9)
C23—C22—H22A109.8 (9)C4—N3—C1117.28 (9)
C23—C22—H22B109.7 (9)N1—C1—N2117.21 (9)
H22A—C22—H22B106.1 (12)N1—C1—N3119.07 (10)
C22—C23—C24109.04 (9)N3—C1—N2123.71 (10)
C22—C23—H23A109.4 (8)N2—C2—C3123.18 (10)
C22—C23—H23B109.3 (8)N2—C2—H2117.8 (10)
C24—C23—H23A109.9 (8)C3—C2—H2119.0 (10)
C24—C23—H23B109.8 (8)C2—C3—H3A123.5 (10)
H23A—C23—H23B109.3 (11)C4—C3—C2115.66 (11)
C23—C24—H24A109.4 (8)C4—C3—H3A120.8 (10)
C23—C24—H24B111.7 (8)N3—C4—C3123.09 (10)
C25—C24—C23116.40 (9)N3—C4—H4119.0 (10)
C25—C24—H24A105.5 (9)C3—C4—H4117.9 (10)
C25—C24—H24B106.9 (8)
O1—C21—C22—C23175.72 (9)C1—N2—C2—C30.26 (17)
O2—C21—C22—C234.43 (17)C1—N3—C4—C30.59 (17)
C21—C22—C23—C24179.45 (9)C2—N2—C1—N1178.48 (10)
C22—C23—C24—C25179.14 (9)C2—N2—C1—N31.20 (16)
C23—C24—C25—O39.08 (14)C2—C3—C4—N30.71 (18)
C23—C24—C25—O4172.23 (10)C4—N3—C1—N1178.06 (10)
N2—C2—C3—C41.16 (18)C4—N3—C1—N21.61 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N30.91 (3)1.76 (3)2.6659 (12)178 (2)
O3—H3···N2i0.92 (2)1.78 (2)2.6774 (12)166 (2)
N1—H1A···O4ii0.872 (19)2.209 (19)2.9302 (14)139.8 (16)
N1—H1B···O4iii0.860 (19)2.035 (19)2.8938 (12)176.0 (16)
Symmetry codes: (i) x1, y, z1; (ii) x, y+1, z+1; (iii) x+1, y, z+1.
(III) Pyrimidin-2-amine–glutaric acid (2/1) top
Crystal data top
2C4H5N3·C5H8O4F(000) = 680
Mr = 322.33Dx = 1.347 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.2625 (4) ÅCell parameters from 3520 reflections
b = 15.0558 (6) Åθ = 2.4–31.0°
c = 11.1755 (4) ŵ = 0.10 mm1
β = 113.032 (1)°T = 120 K
V = 1589.08 (11) Å3Block, dull light colourless
Z = 40.34 × 0.32 × 0.15 mm
Data collection top
Bruker SMART CCD 6000 area-detector
diffractometer
3041 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, sealed X-ray tubeRint = 0.036
Graphite monochromatorθmax = 29.5°, θmin = 2.3°
Detector resolution: 5.6 pixels mm-1h = 1014
ω scansk = 2020
12296 measured reflectionsl = 1315
4412 independent reflections
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)] = 0.043Hydrogen site location: difference Fourier map
wR(F2) = 0.123All H-atom parameters refined
S = 0.99 w = 1/[σ2(Fo2) + (0.070P)2]
where P = (Fo2 + 2Fc2)/3
4412 reflections(Δ/σ)max = 0.001
280 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.27 e Å3
Special details top

Experimental. The data collection nominally covered a full sphere of reciprocal space by a combination of 3 sets of ω scans each set at different φ and/or 2θ angles and each scan (5 s exposure) covering -0.300° degrees in ω. The crystal to detector distance was 4.85 cm.

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
O10.68972 (11)0.63776 (5)1.01872 (9)0.0321 (2)
O20.69066 (11)0.49164 (6)1.05452 (9)0.0346 (2)
O30.39617 (11)0.35873 (6)0.45576 (8)0.0334 (2)
O40.48362 (10)0.29041 (6)0.64924 (8)0.0317 (2)
C310.65891 (13)0.55456 (8)0.98042 (12)0.0264 (3)
C320.57995 (16)0.54654 (8)0.83610 (12)0.0291 (3)
C330.54088 (14)0.45193 (8)0.78846 (11)0.0252 (3)
C340.47157 (15)0.44969 (8)0.64170 (11)0.0258 (3)
C350.45143 (13)0.35799 (8)0.58448 (11)0.0248 (3)
H10.7370 (19)0.6431 (11)1.1104 (18)0.054 (5)*
H30.391 (2)0.2974 (13)0.4157 (18)0.073 (6)*
H32A0.4931 (17)0.5837 (11)0.8104 (15)0.046 (4)*
H32B0.6422 (16)0.5732 (11)0.7983 (15)0.043 (4)*
H33A0.6298 (15)0.4162 (10)0.8216 (13)0.030 (4)*
H33B0.4775 (15)0.4272 (10)0.8263 (13)0.031 (4)*
H34A0.3760 (16)0.4792 (10)0.6086 (14)0.031 (4)*
H34B0.5290 (17)0.4826 (10)0.6055 (15)0.038 (4)*
N10.86027 (13)0.51591 (7)0.33091 (11)0.0293 (3)
N20.80550 (11)0.66261 (7)0.27509 (10)0.0279 (2)
N30.93238 (12)0.61994 (7)0.49646 (10)0.0289 (2)
C10.86719 (13)0.60143 (8)0.36838 (12)0.0253 (3)
C20.80468 (15)0.74611 (8)0.31460 (13)0.0311 (3)
C30.86327 (15)0.77124 (9)0.44277 (13)0.0317 (3)
C40.92825 (14)0.70457 (8)0.53077 (13)0.0307 (3)
H1A0.8247 (17)0.5046 (10)0.2438 (17)0.041 (4)*
H1B0.9212 (19)0.4787 (11)0.3878 (16)0.046 (5)*
H20.7613 (15)0.7882 (9)0.2452 (13)0.029 (4)*
H3A0.8596 (16)0.8299 (11)0.4692 (14)0.037 (4)*
H40.9753 (16)0.7183 (10)0.6248 (15)0.037 (4)*
N210.48258 (13)0.12266 (8)0.52422 (11)0.0351 (3)
N220.37737 (12)0.20413 (7)0.33644 (10)0.0296 (2)
N230.40845 (12)0.04683 (7)0.32978 (11)0.0314 (3)
C210.42208 (14)0.12440 (8)0.39505 (12)0.0280 (3)
C220.31796 (15)0.20493 (9)0.20696 (13)0.0316 (3)
C230.30087 (15)0.12904 (9)0.13313 (14)0.0333 (3)
C240.34809 (14)0.05092 (9)0.20099 (13)0.0326 (3)
H21A0.4872 (17)0.1747 (12)0.5681 (15)0.048 (5)*
H21B0.5110 (17)0.0677 (12)0.5681 (16)0.046 (4)*
H220.2861 (15)0.2618 (10)0.1669 (13)0.030 (4)*
H230.2582 (16)0.1320 (10)0.0399 (16)0.040 (4)*
H240.3369 (15)0.0050 (10)0.1539 (14)0.031 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0473 (6)0.0204 (4)0.0236 (5)0.0021 (4)0.0084 (4)0.0019 (3)
O20.0497 (6)0.0223 (4)0.0250 (5)0.0006 (4)0.0072 (4)0.0011 (3)
O30.0505 (6)0.0237 (5)0.0212 (5)0.0023 (4)0.0087 (4)0.0015 (3)
O40.0464 (6)0.0216 (4)0.0258 (5)0.0016 (4)0.0125 (4)0.0012 (3)
C310.0317 (7)0.0220 (6)0.0257 (6)0.0002 (5)0.0114 (5)0.0017 (4)
C320.0420 (8)0.0213 (6)0.0227 (6)0.0002 (5)0.0114 (5)0.0007 (4)
C330.0331 (7)0.0207 (6)0.0219 (6)0.0007 (5)0.0107 (5)0.0003 (4)
C340.0344 (7)0.0210 (6)0.0214 (6)0.0006 (5)0.0103 (5)0.0007 (4)
C350.0288 (7)0.0233 (6)0.0227 (6)0.0029 (5)0.0104 (5)0.0012 (4)
N10.0366 (6)0.0227 (5)0.0241 (6)0.0022 (4)0.0071 (5)0.0017 (4)
N20.0318 (6)0.0224 (5)0.0250 (5)0.0013 (4)0.0064 (4)0.0006 (4)
N30.0346 (6)0.0261 (5)0.0239 (5)0.0009 (4)0.0091 (4)0.0017 (4)
C10.0258 (6)0.0235 (6)0.0257 (6)0.0007 (5)0.0088 (5)0.0009 (4)
C20.0341 (7)0.0227 (6)0.0313 (7)0.0011 (5)0.0072 (5)0.0002 (5)
C30.0353 (7)0.0233 (6)0.0336 (7)0.0022 (5)0.0103 (5)0.0060 (5)
C40.0339 (7)0.0286 (7)0.0273 (7)0.0027 (5)0.0094 (5)0.0056 (5)
N210.0518 (8)0.0223 (6)0.0287 (6)0.0018 (5)0.0131 (5)0.0014 (5)
N220.0367 (6)0.0224 (5)0.0287 (6)0.0030 (4)0.0116 (4)0.0024 (4)
N230.0360 (6)0.0246 (5)0.0340 (6)0.0005 (4)0.0141 (5)0.0048 (4)
C210.0297 (7)0.0237 (6)0.0318 (7)0.0013 (5)0.0132 (5)0.0024 (5)
C220.0367 (8)0.0261 (6)0.0310 (7)0.0036 (5)0.0123 (5)0.0009 (5)
C230.0367 (8)0.0348 (7)0.0278 (7)0.0022 (6)0.0119 (6)0.0045 (5)
C240.0344 (8)0.0295 (7)0.0353 (7)0.0019 (5)0.0153 (6)0.0087 (5)
Geometric parameters (Å, º) top
O1—C311.3215 (14)N2—C21.3336 (16)
O1—H10.950 (19)N3—C11.3508 (16)
O2—C311.2157 (14)N3—C41.3361 (16)
O3—C351.3239 (14)C2—C31.3721 (18)
O3—H31.02 (2)C2—H20.965 (14)
O4—C351.2170 (14)C3—C41.3806 (18)
C31—C321.4999 (17)C3—H3A0.937 (16)
C32—C331.5187 (17)C4—H40.991 (15)
C32—H32A0.994 (17)N21—C211.3299 (17)
C32—H32B0.979 (16)N21—H21A0.915 (18)
C33—C341.5113 (16)N21—H21B0.948 (18)
C33—H33A0.997 (14)N22—C211.3584 (16)
C33—H33B0.978 (14)N22—C221.3324 (17)
C34—C351.5013 (16)N23—C211.3548 (15)
C34—H34A1.006 (15)N23—C241.3271 (17)
C34—H34B0.971 (16)C22—C231.3799 (18)
N1—C11.3472 (15)C22—H220.962 (15)
N1—H1A0.912 (17)C23—C241.3804 (19)
N1—H1B0.893 (18)C23—H230.961 (16)
N2—C11.3490 (16)C24—H240.976 (14)
C31—O1—H1112.7 (10)C4—N3—C1116.28 (11)
C35—O3—H3113.4 (11)N1—C1—N2117.43 (11)
O1—C31—C32112.62 (10)N1—C1—N3118.08 (11)
O2—C31—O1123.47 (11)N2—C1—N3124.48 (11)
O2—C31—C32123.91 (11)N2—C2—C3123.28 (12)
C31—C32—C33114.20 (10)N2—C2—H2114.5 (8)
C31—C32—H32A108.1 (9)C3—C2—H2122.2 (8)
C31—C32—H32B105.2 (9)C2—C3—C4115.81 (12)
C33—C32—H32A110.0 (10)C2—C3—H3A122.2 (9)
C33—C32—H32B111.1 (9)C4—C3—H3A121.9 (9)
H32A—C32—H32B107.9 (13)N3—C4—C3123.34 (12)
C32—C33—H33A107.3 (8)N3—C4—H4116.5 (9)
C32—C33—H33B109.5 (8)C3—C4—H4120.2 (9)
C34—C33—C32110.42 (10)C21—N21—H21A118.0 (10)
C34—C33—H33A111.4 (8)C21—N21—H21B119.8 (10)
C34—C33—H33B110.5 (8)H21A—N21—H21B122.0 (14)
H33A—C33—H33B107.6 (12)C22—N22—C21117.16 (11)
C33—C34—H34A111.5 (8)C24—N23—C21116.74 (11)
C33—C34—H34B109.6 (9)N21—C21—N22117.83 (11)
C35—C34—C33114.24 (10)N21—C21—N23118.26 (12)
C35—C34—H34A107.3 (8)N23—C21—N22123.91 (12)
C35—C34—H34B107.3 (9)N22—C22—C23122.61 (12)
H34A—C34—H34B106.5 (12)N22—C22—H22116.2 (8)
O3—C35—C34112.59 (10)C23—C22—H22121.2 (8)
O4—C35—O3123.66 (11)C22—C23—C24116.22 (13)
O4—C35—C34123.74 (11)C22—C23—H23120.5 (9)
C1—N1—H1A117.5 (10)C24—C23—H23123.3 (9)
C1—N1—H1B116.2 (11)N23—C24—C23123.36 (12)
H1A—N1—H1B121.2 (15)N23—C24—H24116.8 (8)
C2—N2—C1116.72 (11)C23—C24—H24119.8 (8)
O1—C31—C32—C33179.23 (11)C2—C3—C4—N31.6 (2)
O2—C31—C32—C330.4 (2)C4—N3—C1—N1175.37 (12)
C31—C32—C33—C34175.83 (11)C4—N3—C1—N23.12 (19)
C32—C33—C34—C35170.19 (11)N22—C22—C23—C240.5 (2)
C33—C34—C35—O3177.24 (11)C21—N22—C22—C230.2 (2)
C33—C34—C35—O42.08 (19)C21—N23—C24—C230.4 (2)
N2—C2—C3—C41.8 (2)C22—N22—C21—N21179.50 (12)
C1—N2—C2—C30.4 (2)C22—N22—C21—N230.62 (19)
C1—N3—C4—C30.67 (19)C22—C23—C24—N230.8 (2)
C2—N2—C1—N1175.52 (12)C24—N23—C21—N21179.78 (12)
C2—N2—C1—N32.98 (19)C24—N23—C21—N220.34 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N2i0.950 (19)1.719 (19)2.6639 (13)172.4 (17)
O3—H3···N221.02 (2)1.64 (2)2.6518 (13)174.0 (17)
N1—H1A···O2ii0.912 (17)2.031 (17)2.9149 (15)162.6 (14)
N1—H1B···N3iii0.893 (18)2.149 (18)3.0367 (16)172.7 (15)
N21—H21A···O40.915 (18)1.972 (18)2.8843 (14)175.1 (15)
N21—H21B···N23iv0.948 (18)2.055 (18)2.9995 (16)174.6 (14)
Symmetry codes: (i) x, y, z+1; (ii) x, y, z1; (iii) x+2, y+1, z+1; (iv) x+1, y, z+1.
(IV) Bis(2-aminopyrimidinium) glutarate–glutaric acid (1/2) top
Crystal data top
2C4H6N3+·C5H6O42·2C5H8O4Z = 2
Mr = 586.56F(000) = 620
Triclinic, P1Dx = 1.424 Mg m3
a = 5.4848 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.1944 (5) ÅCell parameters from 7339 reflections
c = 22.9123 (11) Åθ = 2.5–31.0°
α = 91.781 (1)°µ = 0.12 mm1
β = 92.371 (1)°T = 120 K
γ = 103.011 (1)°Prism, clear light colourless
V = 1368.32 (12) Å30.56 × 0.48 × 0.3 mm
Data collection top
Bruker SMART CCD 6000 area-detector
diffractometer
7579 independent reflections
Radiation source: sealed X-ray tube, sealed X-ray tube6181 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Detector resolution: 5.6 pixels mm-1θmax = 29.5°, θmin = 1.9°
ω scansh = 77
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
k = 1515
Tmin = 0.451, Tmax = 1.000l = 3131
15931 measured reflections
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)] = 0.039Hydrogen site location: difference Fourier map
wR(F2) = 0.111All H-atom parameters refined
S = 1.05 w = 1/[σ2(Fo2) + (0.060P)2 + 0.260P]
where P = (Fo2 + 2Fc2)/3
7579 reflections(Δ/σ)max < 0.001
506 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.22 e Å3
Special details top

Experimental. Absorption correction: SADABS-2006/1 (Bruker,2006) was used for absorption correction. R(int) was 0.0453 before and 0.0179 after correction. The Ratio of minimum to maximum transmission is 0.4506. The λ/2 correction factor is 0.0015.

The data collection nominally covered a full sphere of reciprocal space by a combination of 3 sets of ω scans each set at different φ angles and each scan (3 s exposure) covering -0.300° degrees in ω. The crystal to detector distance was 4.85 cm.

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
N10.74164 (19)0.50115 (9)0.55845 (4)0.02358 (19)
H1A0.667 (3)0.5281 (14)0.5889 (7)0.033 (4)*
H1B0.896 (3)0.5412 (16)0.5491 (7)0.039 (4)*
N20.75251 (19)0.35661 (10)0.48495 (4)0.0260 (2)
N30.41079 (18)0.33150 (9)0.54674 (4)0.02209 (19)
H30.327 (3)0.3632 (17)0.5796 (8)0.047 (5)*
C10.6367 (2)0.39652 (10)0.53034 (5)0.0212 (2)
C20.6365 (2)0.25248 (12)0.45721 (5)0.0295 (3)
H20.720 (3)0.2254 (14)0.4249 (7)0.031 (4)*
C30.4055 (2)0.18104 (12)0.47231 (6)0.0298 (3)
H3A0.324 (3)0.1027 (15)0.4517 (7)0.031 (4)*
C40.2966 (2)0.22500 (11)0.51838 (5)0.0261 (2)
H40.137 (3)0.1865 (14)0.5329 (7)0.028 (4)*
N210.51819 (19)0.87371 (9)0.05909 (4)0.02289 (19)
H21A0.588 (3)0.8363 (15)0.0858 (7)0.031 (4)*
H21B0.607 (3)0.9470 (17)0.0463 (8)0.047 (5)*
N220.17011 (18)0.71181 (9)0.05092 (4)0.02133 (19)
H220.243 (3)0.6699 (16)0.0788 (8)0.045 (5)*
N230.19675 (18)0.88334 (8)0.00809 (4)0.02194 (19)
C210.2961 (2)0.82320 (10)0.03392 (5)0.0197 (2)
C220.0587 (2)0.65813 (10)0.02684 (5)0.0234 (2)
H22A0.136 (3)0.5779 (14)0.0423 (7)0.027 (4)*
C230.1664 (2)0.71499 (11)0.01545 (5)0.0244 (2)
H230.329 (3)0.6789 (14)0.0341 (7)0.028 (4)*
C240.0272 (2)0.82963 (11)0.03120 (5)0.0233 (2)
H240.092 (3)0.8750 (13)0.0608 (6)0.026 (4)*
O310.29014 (16)0.28725 (7)0.33716 (4)0.02530 (18)
H310.132 (4)0.3180 (18)0.3518 (9)0.058 (6)*
O320.28534 (16)0.11670 (8)0.39024 (4)0.02988 (19)
O331.32610 (17)0.22579 (8)0.30235 (4)0.0312 (2)
H331.400 (4)0.305 (2)0.3164 (9)0.061 (6)*
O341.03244 (17)0.25675 (8)0.36179 (4)0.0333 (2)
C310.3828 (2)0.17173 (10)0.35494 (5)0.0209 (2)
C320.6234 (2)0.11885 (10)0.32588 (5)0.0230 (2)
H32A0.739 (3)0.1737 (15)0.3332 (7)0.037 (4)*
H32B0.583 (3)0.1301 (14)0.2823 (7)0.031 (4)*
C330.7422 (2)0.01351 (10)0.34386 (5)0.0236 (2)
H33A0.617 (3)0.0641 (14)0.3361 (7)0.031 (4)*
H33B0.791 (3)0.0211 (15)0.3874 (7)0.038 (4)*
C340.9763 (2)0.06083 (10)0.31042 (5)0.0228 (2)
H34A1.100 (3)0.0120 (14)0.3155 (7)0.028 (4)*
H34B0.935 (3)0.0581 (15)0.2674 (8)0.039 (4)*
C351.1097 (2)0.19109 (10)0.32794 (5)0.0212 (2)
O410.54306 (15)0.44004 (7)0.34901 (4)0.02515 (17)
O420.84209 (14)0.60795 (7)0.36792 (3)0.02203 (16)
O430.67728 (16)0.72032 (8)0.14741 (4)0.0302 (2)
O440.32959 (15)0.57898 (7)0.12760 (4)0.02490 (17)
C410.74516 (19)0.51051 (9)0.33709 (5)0.0184 (2)
C420.8772 (2)0.48562 (10)0.28302 (5)0.0200 (2)
H42A0.804 (3)0.4006 (13)0.2680 (6)0.023 (3)*
H42B1.056 (3)0.4955 (14)0.2930 (7)0.030 (4)*
C430.84395 (19)0.57577 (10)0.23555 (5)0.0193 (2)
H43A0.909 (3)0.6618 (13)0.2518 (6)0.025 (3)*
H43B0.949 (3)0.5657 (13)0.2019 (7)0.028 (4)*
C440.5715 (2)0.55580 (11)0.21365 (5)0.0229 (2)
H44A0.498 (3)0.4672 (16)0.2050 (7)0.040 (4)*
H44B0.462 (3)0.5834 (15)0.2420 (7)0.039 (4)*
C450.5273 (2)0.62339 (10)0.15951 (5)0.0206 (2)
O510.10781 (18)0.15869 (8)0.19147 (4)0.0368 (2)
H510.042 (4)0.2042 (19)0.1775 (9)0.060 (6)*
O520.02073 (16)0.03209 (7)0.12487 (4)0.02748 (18)
O531.09283 (15)0.36457 (7)0.15514 (4)0.02512 (18)
H531.161 (4)0.4396 (19)0.1419 (9)0.058 (6)*
O540.74059 (15)0.37242 (7)0.10348 (4)0.02663 (18)
C510.1597 (2)0.05632 (9)0.16281 (5)0.0199 (2)
C520.4091 (2)0.02425 (10)0.18254 (5)0.0201 (2)
H52A0.537 (3)0.0277 (14)0.1782 (7)0.029 (4)*
H52B0.403 (3)0.0443 (14)0.2238 (7)0.028 (4)*
C530.4849 (2)0.13960 (9)0.14814 (5)0.0200 (2)
H53A0.368 (3)0.1932 (14)0.1547 (7)0.031 (4)*
H53B0.481 (3)0.1175 (14)0.1061 (7)0.028 (4)*
C540.7494 (2)0.20567 (10)0.16794 (5)0.0212 (2)
H54A0.866 (3)0.1519 (14)0.1616 (7)0.030 (4)*
H54B0.755 (3)0.2283 (14)0.2105 (7)0.033 (4)*
C550.8541 (2)0.32273 (9)0.13804 (5)0.0198 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0218 (5)0.0253 (5)0.0229 (5)0.0031 (4)0.0039 (4)0.0016 (4)
N20.0248 (5)0.0305 (5)0.0230 (5)0.0064 (4)0.0041 (4)0.0006 (4)
N30.0207 (4)0.0245 (4)0.0210 (4)0.0043 (4)0.0023 (3)0.0037 (4)
C10.0200 (5)0.0249 (5)0.0195 (5)0.0061 (4)0.0007 (4)0.0050 (4)
C20.0308 (6)0.0322 (6)0.0251 (6)0.0064 (5)0.0041 (5)0.0026 (5)
C30.0292 (6)0.0300 (6)0.0276 (6)0.0017 (5)0.0001 (5)0.0029 (5)
C40.0236 (5)0.0273 (5)0.0258 (5)0.0025 (4)0.0000 (4)0.0034 (4)
N210.0219 (5)0.0213 (4)0.0248 (5)0.0035 (4)0.0014 (4)0.0034 (4)
N220.0225 (5)0.0200 (4)0.0214 (4)0.0044 (4)0.0010 (3)0.0037 (3)
N230.0229 (5)0.0219 (4)0.0212 (4)0.0053 (4)0.0012 (3)0.0033 (3)
C210.0213 (5)0.0188 (5)0.0194 (5)0.0051 (4)0.0037 (4)0.0002 (4)
C220.0222 (5)0.0221 (5)0.0251 (5)0.0029 (4)0.0033 (4)0.0011 (4)
C230.0210 (5)0.0257 (5)0.0249 (5)0.0020 (4)0.0009 (4)0.0002 (4)
C240.0236 (5)0.0254 (5)0.0216 (5)0.0065 (4)0.0006 (4)0.0038 (4)
O310.0195 (4)0.0215 (4)0.0312 (4)0.0032 (3)0.0033 (3)0.0003 (3)
O320.0270 (4)0.0262 (4)0.0346 (5)0.0017 (3)0.0066 (4)0.0011 (4)
O330.0257 (4)0.0226 (4)0.0407 (5)0.0051 (3)0.0135 (4)0.0047 (4)
O340.0285 (5)0.0252 (4)0.0427 (5)0.0027 (3)0.0136 (4)0.0056 (4)
C310.0175 (5)0.0196 (5)0.0238 (5)0.0007 (4)0.0017 (4)0.0051 (4)
C320.0192 (5)0.0188 (5)0.0287 (6)0.0012 (4)0.0026 (4)0.0034 (4)
C330.0204 (5)0.0191 (5)0.0288 (6)0.0011 (4)0.0028 (4)0.0016 (4)
C340.0199 (5)0.0176 (5)0.0290 (6)0.0001 (4)0.0029 (4)0.0021 (4)
C350.0181 (5)0.0192 (5)0.0245 (5)0.0003 (4)0.0009 (4)0.0039 (4)
O410.0223 (4)0.0216 (4)0.0274 (4)0.0045 (3)0.0070 (3)0.0004 (3)
O420.0191 (4)0.0211 (4)0.0227 (4)0.0021 (3)0.0028 (3)0.0011 (3)
O430.0242 (4)0.0257 (4)0.0339 (5)0.0087 (3)0.0067 (3)0.0127 (3)
O440.0204 (4)0.0208 (4)0.0295 (4)0.0033 (3)0.0056 (3)0.0080 (3)
C410.0166 (5)0.0179 (4)0.0196 (5)0.0017 (4)0.0003 (4)0.0043 (4)
C420.0192 (5)0.0184 (5)0.0217 (5)0.0023 (4)0.0035 (4)0.0029 (4)
C430.0175 (5)0.0201 (5)0.0187 (5)0.0001 (4)0.0016 (4)0.0032 (4)
C440.0189 (5)0.0237 (5)0.0230 (5)0.0022 (4)0.0004 (4)0.0071 (4)
C450.0173 (5)0.0186 (5)0.0239 (5)0.0006 (4)0.0002 (4)0.0034 (4)
O510.0310 (5)0.0274 (4)0.0418 (5)0.0139 (4)0.0146 (4)0.0181 (4)
O520.0220 (4)0.0224 (4)0.0352 (5)0.0010 (3)0.0048 (3)0.0089 (3)
O530.0186 (4)0.0185 (4)0.0348 (4)0.0030 (3)0.0032 (3)0.0066 (3)
O540.0217 (4)0.0230 (4)0.0339 (4)0.0021 (3)0.0014 (3)0.0076 (3)
C510.0192 (5)0.0166 (4)0.0219 (5)0.0006 (4)0.0023 (4)0.0021 (4)
C520.0188 (5)0.0168 (4)0.0217 (5)0.0023 (4)0.0004 (4)0.0023 (4)
C530.0169 (5)0.0162 (4)0.0251 (5)0.0005 (4)0.0006 (4)0.0025 (4)
C540.0191 (5)0.0163 (4)0.0260 (5)0.0009 (4)0.0006 (4)0.0035 (4)
C550.0179 (5)0.0155 (4)0.0246 (5)0.0006 (4)0.0019 (4)0.0001 (4)
Geometric parameters (Å, º) top
N1—H1A0.900 (16)C33—H33A0.997 (16)
N1—H1B0.902 (18)C33—H33B1.018 (17)
N1—C11.3179 (15)C33—C341.5220 (15)
N2—C11.3558 (14)C34—H34A0.970 (15)
N2—C21.3245 (17)C34—H34B1.001 (17)
N3—H30.994 (19)C34—C351.5107 (15)
N3—C11.3623 (14)O41—C411.2532 (13)
N3—C41.3484 (16)O42—C411.2773 (13)
C2—H20.964 (16)O43—C451.2517 (13)
C2—C31.4005 (18)O44—C451.2753 (14)
C3—H3A0.986 (16)C41—C421.5100 (14)
C3—C41.3658 (17)C42—H42A0.991 (14)
C4—H40.964 (15)C42—H42B0.978 (16)
N21—H21A0.873 (17)C42—C431.5392 (15)
N21—H21B0.917 (19)C43—H43A1.003 (14)
N21—C211.3219 (15)C43—H43B1.002 (15)
N22—H220.933 (19)C43—C441.5217 (15)
N22—C211.3596 (14)C44—H44A0.994 (17)
N22—C221.3500 (15)C44—H44B0.988 (17)
N23—C211.3560 (14)C44—C451.5119 (15)
N23—C241.3208 (15)O51—H510.90 (2)
C22—H22A0.986 (15)O51—C511.3195 (13)
C22—C231.3616 (16)O52—C511.2097 (14)
C23—H230.966 (16)O53—H530.91 (2)
C23—C241.4037 (16)O53—C551.3254 (13)
C24—H240.962 (15)O54—C551.2111 (14)
O31—H310.94 (2)C51—C521.5021 (15)
O31—C311.3231 (13)C52—H52A1.015 (15)
O32—C311.2133 (14)C52—H52B0.970 (15)
O33—H330.93 (2)C52—C531.5200 (14)
O33—C351.3293 (13)C53—H53A0.983 (15)
O34—C351.2056 (14)C53—H53B0.985 (15)
C31—C321.5103 (15)C53—C541.5162 (15)
C32—H32A0.990 (17)C54—H54A0.982 (15)
C32—H32B1.011 (16)C54—H54B0.998 (16)
C32—C331.5150 (15)C54—C551.5054 (14)
H1A—N1—H1B120.5 (15)H34A—C34—H34B105.8 (13)
C1—N1—H1A120.4 (11)C35—C34—C33113.74 (10)
C1—N1—H1B118.9 (11)C35—C34—H34A105.8 (9)
C2—N2—C1117.28 (10)C35—C34—H34B107.3 (10)
C1—N3—H3119.9 (11)O33—C35—C34112.42 (10)
C4—N3—H3119.3 (11)O34—C35—O33123.14 (10)
C4—N3—C1120.79 (10)O34—C35—C34124.44 (10)
N1—C1—N2119.60 (10)O41—C41—O42122.31 (10)
N1—C1—N3119.27 (10)O41—C41—C42120.32 (10)
N2—C1—N3121.12 (11)O42—C41—C42117.30 (9)
N2—C2—H2116.5 (10)C41—C42—H42A108.7 (8)
N2—C2—C3124.25 (11)C41—C42—H42B109.3 (9)
C3—C2—H2119.3 (10)C41—C42—C43110.42 (8)
C2—C3—H3A122.9 (9)H42A—C42—H42B110.0 (12)
C4—C3—C2116.26 (12)C43—C42—H42A109.3 (8)
C4—C3—H3A120.8 (9)C43—C42—H42B109.1 (9)
N3—C4—C3120.29 (11)C42—C43—H43A108.9 (8)
N3—C4—H4114.5 (9)C42—C43—H43B109.9 (8)
C3—C4—H4125.2 (9)H43A—C43—H43B106.1 (12)
H21A—N21—H21B119.1 (16)C44—C43—C42111.55 (8)
C21—N21—H21A121.5 (11)C44—C43—H43A111.0 (8)
C21—N21—H21B119.3 (12)C44—C43—H43B109.2 (9)
C21—N22—H22120.2 (11)C43—C44—H44A110.7 (10)
C22—N22—H22118.8 (11)C43—C44—H44B113.9 (10)
C22—N22—C21121.03 (10)H44A—C44—H44B106.0 (14)
C24—N23—C21117.21 (9)C45—C44—C43115.21 (9)
N21—C21—N22119.32 (10)C45—C44—H44A107.3 (10)
N21—C21—N23119.66 (10)C45—C44—H44B102.9 (10)
N23—C21—N22121.02 (10)O43—C45—O44121.71 (10)
N22—C22—H22A115.0 (9)O43—C45—C44120.91 (10)
N22—C22—C23120.12 (10)O44—C45—C44117.37 (9)
C23—C22—H22A124.8 (9)C51—O51—H51108.7 (13)
C22—C23—H23122.5 (9)C55—O53—H53113.5 (13)
C22—C23—C24116.21 (11)O51—C51—C52112.22 (9)
C24—C23—H23121.3 (9)O52—C51—O51123.03 (10)
N23—C24—C23124.39 (11)O52—C51—C52124.75 (9)
N23—C24—H24114.9 (9)C51—C52—H52A106.5 (9)
C23—C24—H24120.7 (9)C51—C52—H52B107.5 (9)
C31—O31—H31111.7 (12)C51—C52—C53114.20 (9)
C35—O33—H33107.4 (12)H52A—C52—H52B107.8 (12)
O31—C31—C32111.24 (9)C53—C52—H52A109.5 (9)
O32—C31—O31123.73 (10)C53—C52—H52B111.1 (9)
O32—C31—C32125.03 (10)C52—C53—H53A109.8 (9)
C31—C32—H32A107.6 (10)C52—C53—H53B109.9 (9)
C31—C32—H32B106.2 (9)H53A—C53—H53B109.1 (12)
C31—C32—C33114.65 (10)C54—C53—C52108.98 (9)
H32A—C32—H32B103.5 (13)C54—C53—H53A110.2 (9)
C33—C32—H32A112.1 (10)C54—C53—H53B108.9 (9)
C33—C32—H32B112.0 (9)C53—C54—H54A110.1 (9)
C32—C33—H33A108.6 (9)C53—C54—H54B109.4 (9)
C32—C33—H33B110.1 (9)H54A—C54—H54B108.6 (13)
C32—C33—C34111.02 (10)C55—C54—C53115.86 (9)
H33A—C33—H33B108.3 (13)C55—C54—H54A106.4 (9)
C34—C33—H33A110.2 (9)C55—C54—H54B106.1 (9)
C34—C33—H33B108.6 (10)O53—C55—C54109.69 (9)
C33—C34—H34A112.8 (9)O54—C55—O53124.34 (10)
C33—C34—H34B110.9 (10)O54—C55—C54125.97 (10)
N2—C2—C3—C40.8 (2)O32—C31—C32—C330.26 (17)
C1—N2—C2—C30.92 (19)C31—C32—C33—C34177.34 (9)
C1—N3—C4—C30.48 (17)C32—C33—C34—C35177.82 (10)
C2—N2—C1—N1178.35 (11)C33—C34—C35—O33173.73 (10)
C2—N2—C1—N30.30 (16)C33—C34—C35—O345.45 (17)
C2—C3—C4—N30.09 (18)O41—C41—C42—C43105.43 (11)
C4—N3—C1—N1179.04 (10)O42—C41—C42—C4371.56 (12)
C4—N3—C1—N20.39 (16)C41—C42—C43—C4465.71 (12)
N22—C22—C23—C240.37 (16)C42—C43—C44—C45169.11 (9)
C21—N22—C22—C230.46 (16)C43—C44—C45—O4326.06 (16)
C21—N23—C24—C230.49 (17)C43—C44—C45—O44155.25 (10)
C22—N22—C21—N21179.02 (10)O51—C51—C52—C53176.30 (10)
C22—N22—C21—N230.56 (16)O52—C51—C52—C533.27 (16)
C22—C23—C24—N230.41 (17)C51—C52—C53—C54174.19 (9)
C24—N23—C21—N21179.03 (10)C52—C53—C54—C55179.96 (9)
C24—N23—C21—N220.55 (15)C53—C54—C55—O53174.00 (9)
O31—C31—C32—C33180.00 (10)C53—C54—C55—O545.96 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···N2i0.902 (18)2.196 (18)3.0918 (14)172.3 (15)
N1—H1A···O41ii0.900 (16)1.942 (16)2.8315 (13)169.4 (15)
N3—H3···O42ii0.994 (19)1.618 (19)2.6022 (12)170.2 (17)
N21—H21A···O430.873 (17)2.066 (17)2.9240 (13)167.4 (15)
N21—H21B···N23iii0.917 (19)2.190 (19)3.1049 (14)174.9 (16)
N22—H22···O440.933 (19)1.660 (19)2.5853 (12)170.7 (17)
O31—H31···O42iv0.94 (2)1.68 (2)2.6094 (11)169.6 (19)
O33—H33···O41v0.93 (2)1.67 (2)2.6003 (12)173 (2)
O51—H51···O43iv0.90 (2)1.69 (2)2.5899 (12)175 (2)
O53—H53···O44v0.91 (2)1.68 (2)2.5698 (11)169 (2)
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+1, y+1, z+1; (iii) x+1, y+2, z; (iv) x1, y1, z; (v) x+1, y, z.
 

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