Three cocrystals and a cocrystal salt of pyrimidin-2-amine and glutaric acid

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.

Computing details

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)

Crystal data

C4H5N3·C5H8O4	Dx = 1.407 Mg m^−3
Mr = 227.22	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcm	Cell parameters from 2706 reflections
a = 4.1667 (4) Å	θ = 3.2–30.9°
b = 12.6657 (11) Å	µ = 0.11 mm^−1
c = 20.3238 (18) Å	T = 120 K
V = 1072.57 (17) Å^3	Prism, clear light colourless
Z = 4	0.44 × 0.36 × 0.14 mm
F(000) = 480

Data collection

Bruker SMART CCD 6000 area detector diffractometer	1525 independent reflections
Radiation source: sealed X-ray tube, sealed X-ray tube	1208 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 5.6 pixels mm^-1	θmax = 29.5°, θmin = 2.0°
ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Bruker, 2006)	k = −17→17
Tmin = 0.428, Tmax = 1.000	l = −27→27
9365 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: difference Fourier map
wR(F^2) = 0.149	All H-atom parameters refined
S = 1.06	w = 1/[σ^2(Fo^2) + (0.075P)^2 + 0.7P] where P = (Fo^2 + 2Fc^2)/3
1525 reflections	(Δ/σ)max < 0.001
105 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.0812 (3)	0.45503 (8)	0.42387 (5)	0.0274 (3)
O2	0.2865 (3)	0.30700 (9)	0.38120 (5)	0.0307 (3)
N1	0.0630 (5)	0.37091 (15)	0.2500	0.0289 (4)
N2	−0.2000 (3)	0.50020 (10)	0.30879 (6)	0.0236 (3)
C1	−0.1154 (5)	0.45857 (16)	0.2500	0.0228 (4)
C2	−0.3857 (4)	0.58639 (11)	0.30791 (7)	0.0251 (3)
C3	−0.4894 (6)	0.63265 (16)	0.2500	0.0267 (4)
C4	0.2530 (3)	0.36731 (11)	0.42703 (7)	0.0215 (3)
C5	0.4034 (4)	0.35156 (11)	0.49387 (7)	0.0221 (3)
C6	0.5961 (5)	0.2500	0.5000	0.0226 (4)
H1A	0.132 (6)	0.3467 (18)	0.2868 (11)	0.042 (6)*
H1	−0.012 (7)	0.4621 (19)	0.3836 (12)	0.049 (6)*
H2	−0.444 (5)	0.6172 (15)	0.3487 (10)	0.027 (5)*
H3	−0.620 (7)	0.692 (2)	0.2500	0.034 (7)*
H5A	0.232 (4)	0.3555 (14)	0.5261 (9)	0.023 (4)*
H5B	0.539 (5)	0.4150 (16)	0.5018 (10)	0.035 (5)*
H6	0.732 (5)	0.2443 (16)	0.4620 (10)	0.030 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0352 (6)	0.0241 (5)	0.0228 (5)	0.0080 (4)	−0.0021 (4)	−0.0005 (4)
O2	0.0436 (7)	0.0247 (5)	0.0238 (6)	0.0070 (5)	−0.0012 (5)	−0.0022 (4)
N1	0.0393 (11)	0.0262 (9)	0.0212 (9)	0.0084 (8)	0.000	0.000
N2	0.0267 (6)	0.0214 (6)	0.0226 (6)	−0.0005 (5)	0.0007 (4)	−0.0004 (4)
C1	0.0245 (9)	0.0209 (9)	0.0230 (9)	−0.0016 (7)	0.000	0.000
C2	0.0275 (7)	0.0219 (7)	0.0258 (7)	−0.0006 (6)	0.0015 (5)	−0.0025 (5)
C3	0.0286 (10)	0.0215 (9)	0.0300 (10)	0.0031 (8)	0.000	0.000
C4	0.0240 (6)	0.0183 (6)	0.0222 (6)	−0.0007 (5)	0.0023 (5)	0.0021 (5)
C5	0.0249 (7)	0.0185 (6)	0.0229 (7)	−0.0007 (5)	0.0000 (5)	−0.0003 (5)
C6	0.0223 (9)	0.0196 (9)	0.0260 (10)	0.000	0.000	0.0022 (7)

Geometric parameters (Å, º)

O1—C4	1.3234 (17)	C2—H2	0.95 (2)
O1—H1	0.91 (3)	C3—C2^i	1.3840 (19)
O2—C4	1.2127 (18)	C3—H3	0.93 (3)
N1—C1	1.336 (3)	C4—C5	1.509 (2)
N1—H1A	0.86 (2)	C5—C6	1.5216 (17)
N2—C1	1.3527 (15)	C5—H5A	0.970 (19)
N2—C2	1.3381 (19)	C5—H5B	0.99 (2)
C1—N2^i	1.3528 (15)	C6—C5^ii	1.5216 (17)
C2—C3	1.3840 (19)	C6—H6	0.96 (2)
C4—O1—H1	110.9 (15)	O1—C4—C5	112.29 (12)
C1—N1—H1A	118.9 (15)	O2—C4—O1	123.63 (13)
C2—N2—C1	117.18 (13)	O2—C4—C5	124.08 (13)
N1—C1—N2	117.96 (9)	C4—C5—C6	113.86 (11)
N1—C1—N2^i	117.96 (9)	C4—C5—H5A	107.1 (11)
N2—C1—N2^i	124.08 (18)	C4—C5—H5B	105.9 (12)
N2—C2—C3	122.50 (14)	C6—C5—H5A	112.2 (11)
N2—C2—H2	118.2 (12)	C6—C5—H5B	111.8 (12)
C3—C2—H2	119.3 (12)	H5A—C5—H5B	105.4 (16)
C2^i—C3—C2	116.52 (19)	C5—C6—C5^ii	116.29 (17)
C2—C3—H3	121.74 (10)	C5^ii—C6—H6	108.3 (12)
C2^i—C3—H3	121.74 (10)	C5—C6—H6	108.1 (12)
O1—C4—C5—C6	178.52 (12)	C2—N2—C1—N1	−178.29 (16)
O2—C4—C5—C6	−1.9 (2)	C2—N2—C1—N2^i	1.8 (3)
N2—C2—C3—C2^i	−1.3 (3)	C4—C5—C6—C5^ii	−74.96 (10)
C1—N2—C2—C3	−0.2 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.86 (2)	2.08 (2)	2.9381 (14)	173 (2)
O1—H1···N2	0.91 (3)	1.78 (3)	2.6775 (17)	170 (2)

(II) Pyrimidin-2-amine–glutaric acid (1/1)

Crystal data

C4H5N3·C5H8O4	Z = 2
Mr = 227.22	F(000) = 240
Triclinic, P1	Dx = 1.437 Mg m^−3
a = 6.0184 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.4714 (5) Å	Cell parameters from 5873 reflections
c = 12.0911 (7) Å	θ = 2.8–30.9°
α = 84.371 (1)°	µ = 0.11 mm^−1
β = 89.906 (1)°	T = 120 K
γ = 76.094 (2)°	Block, clear light colourless
V = 525.07 (6) Å^3	0.56 × 0.3 × 0.24 mm

Data collection

Bruker SMART CCD 6000 area-detector diffractometer	2794 independent reflections
Radiation source: sealed X-ray tube, sealed X-ray tube	2279 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 5.6 pixels mm^-1	θmax = 29.0°, θmin = 1.7°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2006)	k = −10→10
Tmin = 0.539, Tmax = 1.000	l = −16→16
12033 measured reflections

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: difference Fourier map
wR(F^2) = 0.126	All H-atom parameters refined
S = 1.04	w = 1/[σ^2(Fo^2) + (0.080P)^2 + 0.090P] where P = (Fo^2 + 2Fc^2)/3
2794 reflections	(Δ/σ)max < 0.001
197 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.46021 (15)	0.32178 (13)	0.61425 (6)	0.0309 (2)
O2	0.64621 (15)	0.17335 (12)	0.47659 (6)	0.0312 (2)
O3	0.13451 (14)	0.23991 (12)	0.11736 (6)	0.0279 (2)
O4	−0.21468 (15)	0.42911 (12)	0.11277 (7)	0.0332 (2)
C21	0.47520 (19)	0.26733 (15)	0.51269 (8)	0.0240 (2)
C22	0.24898 (18)	0.33965 (16)	0.45089 (8)	0.0248 (2)
C23	0.24434 (18)	0.30029 (15)	0.33035 (8)	0.0229 (2)
C24	0.00358 (19)	0.38108 (15)	0.28162 (8)	0.0231 (2)
C25	−0.03390 (19)	0.35239 (15)	0.16201 (8)	0.0239 (2)
H1	0.587 (4)	0.273 (3)	0.6584 (19)	0.071 (6)*
H3	0.086 (4)	0.230 (3)	0.0469 (19)	0.064 (6)*
H22A	0.136 (3)	0.285 (2)	0.4930 (13)	0.034 (4)*
H22B	0.201 (3)	0.474 (2)	0.4558 (13)	0.035 (4)*
H23A	0.350 (2)	0.3549 (19)	0.2902 (11)	0.023 (3)*
H23B	0.286 (2)	0.170 (2)	0.3265 (11)	0.024 (3)*
H24A	−0.105 (2)	0.3244 (19)	0.3239 (12)	0.028 (3)*
H24B	−0.046 (2)	0.514 (2)	0.2875 (12)	0.026 (3)*
N1	0.67341 (18)	0.32172 (15)	0.90019 (8)	0.0319 (2)
N2	1.05289 (16)	0.16702 (13)	0.91090 (7)	0.0242 (2)
N3	0.83099 (17)	0.18650 (13)	0.74480 (7)	0.0248 (2)
C1	0.85433 (19)	0.22400 (15)	0.85062 (8)	0.0232 (2)
C2	1.2312 (2)	0.06618 (17)	0.86220 (9)	0.0280 (2)
C3	1.2216 (2)	0.01773 (17)	0.75500 (9)	0.0292 (2)
C4	1.0131 (2)	0.08427 (16)	0.69945 (9)	0.0270 (2)
H1A	0.547 (3)	0.376 (2)	0.8634 (15)	0.047 (5)*
H1B	0.700 (3)	0.357 (2)	0.9633 (15)	0.041 (4)*
H2	1.377 (3)	0.024 (2)	0.9054 (14)	0.042 (4)*
H4	0.999 (3)	0.051 (2)	0.6219 (14)	0.039 (4)*
H3A	1.347 (3)	−0.056 (2)	0.7205 (14)	0.039 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0322 (4)	0.0432 (5)	0.0151 (4)	−0.0021 (4)	−0.0052 (3)	−0.0096 (3)
O2	0.0294 (4)	0.0422 (5)	0.0197 (4)	−0.0017 (3)	−0.0034 (3)	−0.0094 (3)
O3	0.0276 (4)	0.0387 (5)	0.0163 (4)	−0.0038 (3)	−0.0043 (3)	−0.0082 (3)
O4	0.0349 (5)	0.0363 (5)	0.0231 (4)	0.0039 (3)	−0.0124 (3)	−0.0087 (3)
C21	0.0294 (5)	0.0296 (5)	0.0145 (4)	−0.0091 (4)	−0.0027 (4)	−0.0040 (4)
C22	0.0244 (5)	0.0349 (6)	0.0154 (4)	−0.0065 (4)	−0.0021 (4)	−0.0060 (4)
C23	0.0239 (5)	0.0305 (5)	0.0151 (4)	−0.0070 (4)	−0.0030 (4)	−0.0047 (4)
C24	0.0256 (5)	0.0274 (5)	0.0164 (4)	−0.0052 (4)	−0.0033 (4)	−0.0057 (4)
C25	0.0284 (5)	0.0259 (5)	0.0176 (5)	−0.0071 (4)	−0.0046 (4)	−0.0026 (4)
N1	0.0319 (5)	0.0391 (6)	0.0208 (5)	0.0027 (4)	−0.0087 (4)	−0.0111 (4)
N2	0.0273 (5)	0.0291 (5)	0.0170 (4)	−0.0074 (4)	−0.0042 (3)	−0.0041 (3)
N3	0.0340 (5)	0.0258 (4)	0.0150 (4)	−0.0076 (4)	−0.0055 (3)	−0.0031 (3)
C1	0.0303 (5)	0.0236 (5)	0.0161 (4)	−0.0071 (4)	−0.0050 (4)	−0.0026 (3)
C2	0.0265 (5)	0.0355 (6)	0.0233 (5)	−0.0090 (4)	−0.0026 (4)	−0.0056 (4)
C3	0.0299 (6)	0.0360 (6)	0.0232 (5)	−0.0087 (5)	0.0040 (4)	−0.0082 (4)
C4	0.0376 (6)	0.0287 (5)	0.0176 (5)	−0.0128 (4)	−0.0008 (4)	−0.0046 (4)

Geometric parameters (Å, º)

O1—C21	1.3273 (12)	C24—H24A	0.977 (14)
O1—H1	0.91 (3)	C24—H24B	0.975 (14)
O2—C21	1.2058 (14)	N1—C1	1.3340 (15)
O3—C25	1.3049 (14)	N1—H1A	0.872 (19)
O3—H3	0.92 (2)	N1—H1B	0.860 (19)
O4—C25	1.2256 (13)	N2—C1	1.3557 (13)
C21—C22	1.5081 (14)	N2—C2	1.3274 (15)
C22—C23	1.5165 (14)	N3—C1	1.3509 (13)
C22—H22A	0.990 (15)	N3—C4	1.3279 (15)
C22—H22B	0.987 (16)	C2—C3	1.3844 (15)
C23—C24	1.5244 (15)	C2—H2	0.989 (17)
C23—H23A	0.942 (13)	C3—C4	1.3821 (16)
C23—H23B	0.948 (14)	C3—H3A	0.947 (17)
C24—C25	1.5078 (13)	C4—H4	1.002 (17)
C21—O1—H1	114.4 (14)	H24A—C24—H24B	106.3 (12)
C25—O3—H3	106.6 (14)	O3—C25—C24	115.72 (9)
O1—C21—C22	110.07 (9)	O4—C25—O3	123.60 (9)
O2—C21—O1	124.15 (10)	O4—C25—C24	120.66 (10)
O2—C21—C22	125.77 (9)	C1—N1—H1A	121.7 (12)
C21—C22—C23	116.16 (9)	C1—N1—H1B	116.1 (11)
C21—C22—H22A	106.6 (9)	H1A—N1—H1B	119.6 (17)
C21—C22—H22B	107.9 (9)	C2—N2—C1	117.05 (9)
C23—C22—H22A	109.8 (9)	C4—N3—C1	117.28 (9)
C23—C22—H22B	109.7 (9)	N1—C1—N2	117.21 (9)
H22A—C22—H22B	106.1 (12)	N1—C1—N3	119.07 (10)
C22—C23—C24	109.04 (9)	N3—C1—N2	123.71 (10)
C22—C23—H23A	109.4 (8)	N2—C2—C3	123.18 (10)
C22—C23—H23B	109.3 (8)	N2—C2—H2	117.8 (10)
C24—C23—H23A	109.9 (8)	C3—C2—H2	119.0 (10)
C24—C23—H23B	109.8 (8)	C2—C3—H3A	123.5 (10)
H23A—C23—H23B	109.3 (11)	C4—C3—C2	115.66 (11)
C23—C24—H24A	109.4 (8)	C4—C3—H3A	120.8 (10)
C23—C24—H24B	111.7 (8)	N3—C4—C3	123.09 (10)
C25—C24—C23	116.40 (9)	N3—C4—H4	119.0 (10)
C25—C24—H24A	105.5 (9)	C3—C4—H4	117.9 (10)
C25—C24—H24B	106.9 (8)
O1—C21—C22—C23	175.72 (9)	C1—N2—C2—C3	−0.26 (17)
O2—C21—C22—C23	−4.43 (17)	C1—N3—C4—C3	−0.59 (17)
C21—C22—C23—C24	179.45 (9)	C2—N2—C1—N1	178.48 (10)
C22—C23—C24—C25	−179.14 (9)	C2—N2—C1—N3	−1.20 (16)
C23—C24—C25—O3	9.08 (14)	C2—C3—C4—N3	−0.71 (18)
C23—C24—C25—O4	−172.23 (10)	C4—N3—C1—N1	−178.06 (10)
N2—C2—C3—C4	1.16 (18)	C4—N3—C1—N2	1.61 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3	0.91 (3)	1.76 (3)	2.6659 (12)	178 (2)
O3—H3···N2^i	0.92 (2)	1.78 (2)	2.6774 (12)	166 (2)
N1—H1A···O4^ii	0.872 (19)	2.209 (19)	2.9302 (14)	139.8 (16)
N1—H1B···O4^iii	0.860 (19)	2.035 (19)	2.8938 (12)	176.0 (16)

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

(III) Pyrimidin-2-amine–glutaric acid (2/1)

Crystal data

2C4H5N3·C5H8O4	F(000) = 680
Mr = 322.33	Dx = 1.347 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.2625 (4) Å	Cell parameters from 3520 reflections
b = 15.0558 (6) Å	θ = 2.4–31.0°
c = 11.1755 (4) Å	µ = 0.10 mm^−1
β = 113.032 (1)°	T = 120 K
V = 1589.08 (11) Å^3	Block, dull light colourless
Z = 4	0.34 × 0.32 × 0.15 mm

Data collection

Bruker SMART CCD 6000 area-detector diffractometer	3041 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, sealed X-ray tube	Rint = 0.036
Graphite monochromator	θmax = 29.5°, θmin = 2.3°
Detector resolution: 5.6 pixels mm^-1	h = −10→14
ω scans	k = −20→20
12296 measured reflections	l = −13→15
4412 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: difference Fourier map
wR(F^2) = 0.123	All H-atom parameters refined
S = 0.99	w = 1/[σ^2(Fo^2) + (0.070P)^2] where P = (Fo^2 + 2Fc^2)/3
4412 reflections	(Δ/σ)max = 0.001
280 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.68972 (11)	0.63776 (5)	1.01872 (9)	0.0321 (2)
O2	0.69066 (11)	0.49164 (6)	1.05452 (9)	0.0346 (2)
O3	0.39617 (11)	0.35873 (6)	0.45576 (8)	0.0334 (2)
O4	0.48362 (10)	0.29041 (6)	0.64924 (8)	0.0317 (2)
C31	0.65891 (13)	0.55456 (8)	0.98042 (12)	0.0264 (3)
C32	0.57995 (16)	0.54654 (8)	0.83610 (12)	0.0291 (3)
C33	0.54088 (14)	0.45193 (8)	0.78846 (11)	0.0252 (3)
C34	0.47157 (15)	0.44969 (8)	0.64170 (11)	0.0258 (3)
C35	0.45143 (13)	0.35799 (8)	0.58448 (11)	0.0248 (3)
H1	0.7370 (19)	0.6431 (11)	1.1104 (18)	0.054 (5)*
H3	0.391 (2)	0.2974 (13)	0.4157 (18)	0.073 (6)*
H32A	0.4931 (17)	0.5837 (11)	0.8104 (15)	0.046 (4)*
H32B	0.6422 (16)	0.5732 (11)	0.7983 (15)	0.043 (4)*
H33A	0.6298 (15)	0.4162 (10)	0.8216 (13)	0.030 (4)*
H33B	0.4775 (15)	0.4272 (10)	0.8263 (13)	0.031 (4)*
H34A	0.3760 (16)	0.4792 (10)	0.6086 (14)	0.031 (4)*
H34B	0.5290 (17)	0.4826 (10)	0.6055 (15)	0.038 (4)*
N1	0.86027 (13)	0.51591 (7)	0.33091 (11)	0.0293 (3)
N2	0.80550 (11)	0.66261 (7)	0.27509 (10)	0.0279 (2)
N3	0.93238 (12)	0.61994 (7)	0.49646 (10)	0.0289 (2)
C1	0.86719 (13)	0.60143 (8)	0.36838 (12)	0.0253 (3)
C2	0.80468 (15)	0.74611 (8)	0.31460 (13)	0.0311 (3)
C3	0.86327 (15)	0.77124 (9)	0.44277 (13)	0.0317 (3)
C4	0.92825 (14)	0.70457 (8)	0.53077 (13)	0.0307 (3)
H1A	0.8247 (17)	0.5046 (10)	0.2438 (17)	0.041 (4)*
H1B	0.9212 (19)	0.4787 (11)	0.3878 (16)	0.046 (5)*
H2	0.7613 (15)	0.7882 (9)	0.2452 (13)	0.029 (4)*
H3A	0.8596 (16)	0.8299 (11)	0.4692 (14)	0.037 (4)*
H4	0.9753 (16)	0.7183 (10)	0.6248 (15)	0.037 (4)*
N21	0.48258 (13)	0.12266 (8)	0.52422 (11)	0.0351 (3)
N22	0.37737 (12)	0.20413 (7)	0.33644 (10)	0.0296 (2)
N23	0.40845 (12)	0.04683 (7)	0.32978 (11)	0.0314 (3)
C21	0.42208 (14)	0.12440 (8)	0.39505 (12)	0.0280 (3)
C22	0.31796 (15)	0.20493 (9)	0.20696 (13)	0.0316 (3)
C23	0.30087 (15)	0.12904 (9)	0.13313 (14)	0.0333 (3)
C24	0.34809 (14)	0.05092 (9)	0.20099 (13)	0.0326 (3)
H21A	0.4872 (17)	0.1747 (12)	0.5681 (15)	0.048 (5)*
H21B	0.5110 (17)	0.0677 (12)	0.5681 (16)	0.046 (4)*
H22	0.2861 (15)	0.2618 (10)	0.1669 (13)	0.030 (4)*
H23	0.2582 (16)	0.1320 (10)	0.0399 (16)	0.040 (4)*
H24	0.3369 (15)	−0.0050 (10)	0.1539 (14)	0.031 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0473 (6)	0.0204 (4)	0.0236 (5)	−0.0021 (4)	0.0084 (4)	−0.0019 (3)
O2	0.0497 (6)	0.0223 (4)	0.0250 (5)	0.0006 (4)	0.0072 (4)	0.0011 (3)
O3	0.0505 (6)	0.0237 (5)	0.0212 (5)	−0.0023 (4)	0.0087 (4)	−0.0015 (3)
O4	0.0464 (6)	0.0216 (4)	0.0258 (5)	−0.0016 (4)	0.0125 (4)	0.0012 (3)
C31	0.0317 (7)	0.0220 (6)	0.0257 (6)	0.0002 (5)	0.0114 (5)	−0.0017 (4)
C32	0.0420 (8)	0.0213 (6)	0.0227 (6)	0.0002 (5)	0.0114 (5)	−0.0007 (4)
C33	0.0331 (7)	0.0207 (6)	0.0219 (6)	−0.0007 (5)	0.0107 (5)	−0.0003 (4)
C34	0.0344 (7)	0.0210 (6)	0.0214 (6)	−0.0006 (5)	0.0103 (5)	−0.0007 (4)
C35	0.0288 (7)	0.0233 (6)	0.0227 (6)	−0.0029 (5)	0.0104 (5)	−0.0012 (4)
N1	0.0366 (6)	0.0227 (5)	0.0241 (6)	0.0022 (4)	0.0071 (5)	−0.0017 (4)
N2	0.0318 (6)	0.0224 (5)	0.0250 (5)	−0.0013 (4)	0.0064 (4)	−0.0006 (4)
N3	0.0346 (6)	0.0261 (5)	0.0239 (5)	0.0009 (4)	0.0091 (4)	−0.0017 (4)
C1	0.0258 (6)	0.0235 (6)	0.0257 (6)	−0.0007 (5)	0.0088 (5)	−0.0009 (4)
C2	0.0341 (7)	0.0227 (6)	0.0313 (7)	−0.0011 (5)	0.0072 (5)	0.0002 (5)
C3	0.0353 (7)	0.0233 (6)	0.0336 (7)	−0.0022 (5)	0.0103 (5)	−0.0060 (5)
C4	0.0339 (7)	0.0286 (7)	0.0273 (7)	−0.0027 (5)	0.0094 (5)	−0.0056 (5)
N21	0.0518 (8)	0.0223 (6)	0.0287 (6)	0.0018 (5)	0.0131 (5)	−0.0014 (5)
N22	0.0367 (6)	0.0224 (5)	0.0287 (6)	−0.0030 (4)	0.0116 (4)	−0.0024 (4)
N23	0.0360 (6)	0.0246 (5)	0.0340 (6)	0.0005 (4)	0.0141 (5)	−0.0048 (4)
C21	0.0297 (7)	0.0237 (6)	0.0318 (7)	−0.0013 (5)	0.0132 (5)	−0.0024 (5)
C22	0.0367 (8)	0.0261 (6)	0.0310 (7)	−0.0036 (5)	0.0123 (5)	−0.0009 (5)
C23	0.0367 (8)	0.0348 (7)	0.0278 (7)	−0.0022 (6)	0.0119 (6)	−0.0045 (5)
C24	0.0344 (8)	0.0295 (7)	0.0353 (7)	−0.0019 (5)	0.0153 (6)	−0.0087 (5)

Geometric parameters (Å, º)

O1—C31	1.3215 (14)	N2—C2	1.3336 (16)
O1—H1	0.950 (19)	N3—C1	1.3508 (16)
O2—C31	1.2157 (14)	N3—C4	1.3361 (16)
O3—C35	1.3239 (14)	C2—C3	1.3721 (18)
O3—H3	1.02 (2)	C2—H2	0.965 (14)
O4—C35	1.2170 (14)	C3—C4	1.3806 (18)
C31—C32	1.4999 (17)	C3—H3A	0.937 (16)
C32—C33	1.5187 (17)	C4—H4	0.991 (15)
C32—H32A	0.994 (17)	N21—C21	1.3299 (17)
C32—H32B	0.979 (16)	N21—H21A	0.915 (18)
C33—C34	1.5113 (16)	N21—H21B	0.948 (18)
C33—H33A	0.997 (14)	N22—C21	1.3584 (16)
C33—H33B	0.978 (14)	N22—C22	1.3324 (17)
C34—C35	1.5013 (16)	N23—C21	1.3548 (15)
C34—H34A	1.006 (15)	N23—C24	1.3271 (17)
C34—H34B	0.971 (16)	C22—C23	1.3799 (18)
N1—C1	1.3472 (15)	C22—H22	0.962 (15)
N1—H1A	0.912 (17)	C23—C24	1.3804 (19)
N1—H1B	0.893 (18)	C23—H23	0.961 (16)
N2—C1	1.3490 (16)	C24—H24	0.976 (14)
C31—O1—H1	112.7 (10)	C4—N3—C1	116.28 (11)
C35—O3—H3	113.4 (11)	N1—C1—N2	117.43 (11)
O1—C31—C32	112.62 (10)	N1—C1—N3	118.08 (11)
O2—C31—O1	123.47 (11)	N2—C1—N3	124.48 (11)
O2—C31—C32	123.91 (11)	N2—C2—C3	123.28 (12)
C31—C32—C33	114.20 (10)	N2—C2—H2	114.5 (8)
C31—C32—H32A	108.1 (9)	C3—C2—H2	122.2 (8)
C31—C32—H32B	105.2 (9)	C2—C3—C4	115.81 (12)
C33—C32—H32A	110.0 (10)	C2—C3—H3A	122.2 (9)
C33—C32—H32B	111.1 (9)	C4—C3—H3A	121.9 (9)
H32A—C32—H32B	107.9 (13)	N3—C4—C3	123.34 (12)
C32—C33—H33A	107.3 (8)	N3—C4—H4	116.5 (9)
C32—C33—H33B	109.5 (8)	C3—C4—H4	120.2 (9)
C34—C33—C32	110.42 (10)	C21—N21—H21A	118.0 (10)
C34—C33—H33A	111.4 (8)	C21—N21—H21B	119.8 (10)
C34—C33—H33B	110.5 (8)	H21A—N21—H21B	122.0 (14)
H33A—C33—H33B	107.6 (12)	C22—N22—C21	117.16 (11)
C33—C34—H34A	111.5 (8)	C24—N23—C21	116.74 (11)
C33—C34—H34B	109.6 (9)	N21—C21—N22	117.83 (11)
C35—C34—C33	114.24 (10)	N21—C21—N23	118.26 (12)
C35—C34—H34A	107.3 (8)	N23—C21—N22	123.91 (12)
C35—C34—H34B	107.3 (9)	N22—C22—C23	122.61 (12)
H34A—C34—H34B	106.5 (12)	N22—C22—H22	116.2 (8)
O3—C35—C34	112.59 (10)	C23—C22—H22	121.2 (8)
O4—C35—O3	123.66 (11)	C22—C23—C24	116.22 (13)
O4—C35—C34	123.74 (11)	C22—C23—H23	120.5 (9)
C1—N1—H1A	117.5 (10)	C24—C23—H23	123.3 (9)
C1—N1—H1B	116.2 (11)	N23—C24—C23	123.36 (12)
H1A—N1—H1B	121.2 (15)	N23—C24—H24	116.8 (8)
C2—N2—C1	116.72 (11)	C23—C24—H24	119.8 (8)
O1—C31—C32—C33	−179.23 (11)	C2—C3—C4—N3	−1.6 (2)
O2—C31—C32—C33	0.4 (2)	C4—N3—C1—N1	−175.37 (12)
C31—C32—C33—C34	−175.83 (11)	C4—N3—C1—N2	3.12 (19)
C32—C33—C34—C35	170.19 (11)	N22—C22—C23—C24	0.5 (2)
C33—C34—C35—O3	−177.24 (11)	C21—N22—C22—C23	0.2 (2)
C33—C34—C35—O4	2.08 (19)	C21—N23—C24—C23	0.4 (2)
N2—C2—C3—C4	1.8 (2)	C22—N22—C21—N21	179.50 (12)
C1—N2—C2—C3	0.4 (2)	C22—N22—C21—N23	−0.62 (19)
C1—N3—C4—C3	−0.67 (19)	C22—C23—C24—N23	−0.8 (2)
C2—N2—C1—N1	175.52 (12)	C24—N23—C21—N21	−179.78 (12)
C2—N2—C1—N3	−2.98 (19)	C24—N23—C21—N22	0.34 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2^i	0.950 (19)	1.719 (19)	2.6639 (13)	172.4 (17)
O3—H3···N22	1.02 (2)	1.64 (2)	2.6518 (13)	174.0 (17)
N1—H1A···O2^ii	0.912 (17)	2.031 (17)	2.9149 (15)	162.6 (14)
N1—H1B···N3^iii	0.893 (18)	2.149 (18)	3.0367 (16)	172.7 (15)
N21—H21A···O4	0.915 (18)	1.972 (18)	2.8843 (14)	175.1 (15)
N21—H21B···N23^iv	0.948 (18)	2.055 (18)	2.9995 (16)	174.6 (14)

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

(IV) Bis(2-aminopyrimidinium) glutarate–glutaric acid (1/2)

Crystal data

2C4H6N3^+·C5H6O4^2^−·2C5H8O4	Z = 2
Mr = 586.56	F(000) = 620
Triclinic, P1	Dx = 1.424 Mg m^−3
a = 5.4848 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.1944 (5) Å	Cell parameters from 7339 reflections
c = 22.9123 (11) Å	θ = 2.5–31.0°
α = 91.781 (1)°	µ = 0.12 mm^−1
β = 92.371 (1)°	T = 120 K
γ = 103.011 (1)°	Prism, clear light colourless
V = 1368.32 (12) Å^3	0.56 × 0.48 × 0.3 mm

Data collection

Bruker SMART CCD 6000 area-detector diffractometer	7579 independent reflections
Radiation source: sealed X-ray tube, sealed X-ray tube	6181 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 5.6 pixels mm^-1	θmax = 29.5°, θmin = 1.9°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2006)	k = −15→15
Tmin = 0.451, Tmax = 1.000	l = −31→31
15931 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: difference Fourier map
wR(F^2) = 0.111	All H-atom parameters refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.060P)^2 + 0.260P] where P = (Fo^2 + 2Fc^2)/3
7579 reflections	(Δ/σ)max < 0.001
506 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.74164 (19)	0.50115 (9)	0.55845 (4)	0.02358 (19)
H1A	0.667 (3)	0.5281 (14)	0.5889 (7)	0.033 (4)*
H1B	0.896 (3)	0.5412 (16)	0.5491 (7)	0.039 (4)*
N2	0.75251 (19)	0.35661 (10)	0.48495 (4)	0.0260 (2)
N3	0.41079 (18)	0.33150 (9)	0.54674 (4)	0.02209 (19)
H3	0.327 (3)	0.3632 (17)	0.5796 (8)	0.047 (5)*
C1	0.6367 (2)	0.39652 (10)	0.53034 (5)	0.0212 (2)
C2	0.6365 (2)	0.25248 (12)	0.45721 (5)	0.0295 (3)
H2	0.720 (3)	0.2254 (14)	0.4249 (7)	0.031 (4)*
C3	0.4055 (2)	0.18104 (12)	0.47231 (6)	0.0298 (3)
H3A	0.324 (3)	0.1027 (15)	0.4517 (7)	0.031 (4)*
C4	0.2966 (2)	0.22500 (11)	0.51838 (5)	0.0261 (2)
H4	0.137 (3)	0.1865 (14)	0.5329 (7)	0.028 (4)*
N21	0.51819 (19)	0.87371 (9)	0.05909 (4)	0.02289 (19)
H21A	0.588 (3)	0.8363 (15)	0.0858 (7)	0.031 (4)*
H21B	0.607 (3)	0.9470 (17)	0.0463 (8)	0.047 (5)*
N22	0.17011 (18)	0.71181 (9)	0.05092 (4)	0.02133 (19)
H22	0.243 (3)	0.6699 (16)	0.0788 (8)	0.045 (5)*
N23	0.19675 (18)	0.88334 (8)	−0.00809 (4)	0.02194 (19)
C21	0.2961 (2)	0.82320 (10)	0.03392 (5)	0.0197 (2)
C22	−0.0587 (2)	0.65813 (10)	0.02684 (5)	0.0234 (2)
H22A	−0.136 (3)	0.5779 (14)	0.0423 (7)	0.027 (4)*
C23	−0.1664 (2)	0.71499 (11)	−0.01545 (5)	0.0244 (2)
H23	−0.329 (3)	0.6789 (14)	−0.0341 (7)	0.028 (4)*
C24	−0.0272 (2)	0.82963 (11)	−0.03120 (5)	0.0233 (2)
H24	−0.092 (3)	0.8750 (13)	−0.0608 (6)	0.026 (4)*
O31	0.29014 (16)	−0.28725 (7)	0.33716 (4)	0.02530 (18)
H31	0.132 (4)	−0.3180 (18)	0.3518 (9)	0.058 (6)*
O32	0.28534 (16)	−0.11670 (8)	0.39024 (4)	0.02988 (19)
O33	1.32610 (17)	0.22579 (8)	0.30235 (4)	0.0312 (2)
H33	1.400 (4)	0.305 (2)	0.3164 (9)	0.061 (6)*
O34	1.03244 (17)	0.25675 (8)	0.36179 (4)	0.0333 (2)
C31	0.3828 (2)	−0.17173 (10)	0.35494 (5)	0.0209 (2)
C32	0.6234 (2)	−0.11885 (10)	0.32588 (5)	0.0230 (2)
H32A	0.739 (3)	−0.1737 (15)	0.3332 (7)	0.037 (4)*
H32B	0.583 (3)	−0.1301 (14)	0.2823 (7)	0.031 (4)*
C33	0.7422 (2)	0.01351 (10)	0.34386 (5)	0.0236 (2)
H33A	0.617 (3)	0.0641 (14)	0.3361 (7)	0.031 (4)*
H33B	0.791 (3)	0.0211 (15)	0.3874 (7)	0.038 (4)*
C34	0.9763 (2)	0.06083 (10)	0.31042 (5)	0.0228 (2)
H34A	1.100 (3)	0.0120 (14)	0.3155 (7)	0.028 (4)*
H34B	0.935 (3)	0.0581 (15)	0.2674 (8)	0.039 (4)*
C35	1.1097 (2)	0.19109 (10)	0.32794 (5)	0.0212 (2)
O41	0.54306 (15)	0.44004 (7)	0.34901 (4)	0.02515 (17)
O42	0.84209 (14)	0.60795 (7)	0.36792 (3)	0.02203 (16)
O43	0.67728 (16)	0.72032 (8)	0.14741 (4)	0.0302 (2)
O44	0.32959 (15)	0.57898 (7)	0.12760 (4)	0.02490 (17)
C41	0.74516 (19)	0.51051 (9)	0.33709 (5)	0.0184 (2)
C42	0.8772 (2)	0.48562 (10)	0.28302 (5)	0.0200 (2)
H42A	0.804 (3)	0.4006 (13)	0.2680 (6)	0.023 (3)*
H42B	1.056 (3)	0.4955 (14)	0.2930 (7)	0.030 (4)*
C43	0.84395 (19)	0.57577 (10)	0.23555 (5)	0.0193 (2)
H43A	0.909 (3)	0.6618 (13)	0.2518 (6)	0.025 (3)*
H43B	0.949 (3)	0.5657 (13)	0.2019 (7)	0.028 (4)*
C44	0.5715 (2)	0.55580 (11)	0.21365 (5)	0.0229 (2)
H44A	0.498 (3)	0.4672 (16)	0.2050 (7)	0.040 (4)*
H44B	0.462 (3)	0.5834 (15)	0.2420 (7)	0.039 (4)*
C45	0.5273 (2)	0.62339 (10)	0.15951 (5)	0.0206 (2)
O51	0.10781 (18)	−0.15869 (8)	0.19147 (4)	0.0368 (2)
H51	−0.042 (4)	−0.2042 (19)	0.1775 (9)	0.060 (6)*
O52	0.02073 (16)	−0.03209 (7)	0.12487 (4)	0.02748 (18)
O53	1.09283 (15)	0.36457 (7)	0.15514 (4)	0.02512 (18)
H53	1.161 (4)	0.4396 (19)	0.1419 (9)	0.058 (6)*
O54	0.74059 (15)	0.37242 (7)	0.10348 (4)	0.02663 (18)
C51	0.1597 (2)	−0.05632 (9)	0.16281 (5)	0.0199 (2)
C52	0.4091 (2)	0.02425 (10)	0.18254 (5)	0.0201 (2)
H52A	0.537 (3)	−0.0277 (14)	0.1782 (7)	0.029 (4)*
H52B	0.403 (3)	0.0443 (14)	0.2238 (7)	0.028 (4)*
C53	0.4849 (2)	0.13960 (9)	0.14814 (5)	0.0200 (2)
H53A	0.368 (3)	0.1932 (14)	0.1547 (7)	0.031 (4)*
H53B	0.481 (3)	0.1175 (14)	0.1061 (7)	0.028 (4)*
C54	0.7494 (2)	0.20567 (10)	0.16794 (5)	0.0212 (2)
H54A	0.866 (3)	0.1519 (14)	0.1616 (7)	0.030 (4)*
H54B	0.755 (3)	0.2283 (14)	0.2105 (7)	0.033 (4)*
C55	0.8541 (2)	0.32273 (9)	0.13804 (5)	0.0198 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0218 (5)	0.0253 (5)	0.0229 (5)	0.0031 (4)	0.0039 (4)	0.0016 (4)
N2	0.0248 (5)	0.0305 (5)	0.0230 (5)	0.0064 (4)	0.0041 (4)	0.0006 (4)
N3	0.0207 (4)	0.0245 (4)	0.0210 (4)	0.0043 (4)	0.0023 (3)	0.0037 (4)
C1	0.0200 (5)	0.0249 (5)	0.0195 (5)	0.0061 (4)	0.0007 (4)	0.0050 (4)
C2	0.0308 (6)	0.0322 (6)	0.0251 (6)	0.0064 (5)	0.0041 (5)	−0.0026 (5)
C3	0.0292 (6)	0.0300 (6)	0.0276 (6)	0.0017 (5)	−0.0001 (5)	−0.0029 (5)
C4	0.0236 (5)	0.0273 (5)	0.0258 (5)	0.0025 (4)	0.0000 (4)	0.0034 (4)
N21	0.0219 (5)	0.0213 (4)	0.0248 (5)	0.0035 (4)	−0.0014 (4)	0.0034 (4)
N22	0.0225 (5)	0.0200 (4)	0.0214 (4)	0.0044 (4)	0.0010 (3)	0.0037 (3)
N23	0.0229 (5)	0.0219 (4)	0.0212 (4)	0.0053 (4)	0.0012 (3)	0.0033 (3)
C21	0.0213 (5)	0.0188 (5)	0.0194 (5)	0.0051 (4)	0.0037 (4)	0.0002 (4)
C22	0.0222 (5)	0.0221 (5)	0.0251 (5)	0.0029 (4)	0.0033 (4)	0.0011 (4)
C23	0.0210 (5)	0.0257 (5)	0.0249 (5)	0.0020 (4)	0.0009 (4)	−0.0002 (4)
C24	0.0236 (5)	0.0254 (5)	0.0216 (5)	0.0065 (4)	0.0006 (4)	0.0038 (4)
O31	0.0195 (4)	0.0215 (4)	0.0312 (4)	−0.0032 (3)	0.0033 (3)	−0.0003 (3)
O32	0.0270 (4)	0.0262 (4)	0.0346 (5)	0.0017 (3)	0.0066 (4)	−0.0011 (4)
O33	0.0257 (4)	0.0226 (4)	0.0407 (5)	−0.0051 (3)	0.0135 (4)	−0.0047 (4)
O34	0.0285 (5)	0.0252 (4)	0.0427 (5)	−0.0027 (3)	0.0136 (4)	−0.0056 (4)
C31	0.0175 (5)	0.0196 (5)	0.0238 (5)	0.0007 (4)	−0.0017 (4)	0.0051 (4)
C32	0.0192 (5)	0.0188 (5)	0.0287 (6)	−0.0012 (4)	0.0026 (4)	0.0034 (4)
C33	0.0204 (5)	0.0191 (5)	0.0288 (6)	−0.0011 (4)	0.0028 (4)	0.0016 (4)
C34	0.0199 (5)	0.0176 (5)	0.0290 (6)	0.0001 (4)	0.0029 (4)	0.0021 (4)
C35	0.0181 (5)	0.0192 (5)	0.0245 (5)	0.0003 (4)	0.0009 (4)	0.0039 (4)
O41	0.0223 (4)	0.0216 (4)	0.0274 (4)	−0.0045 (3)	0.0070 (3)	−0.0004 (3)
O42	0.0191 (4)	0.0211 (4)	0.0227 (4)	−0.0021 (3)	0.0028 (3)	−0.0011 (3)
O43	0.0242 (4)	0.0257 (4)	0.0339 (5)	−0.0087 (3)	−0.0067 (3)	0.0127 (3)
O44	0.0204 (4)	0.0208 (4)	0.0295 (4)	−0.0033 (3)	−0.0056 (3)	0.0080 (3)
C41	0.0166 (5)	0.0179 (4)	0.0196 (5)	0.0017 (4)	0.0003 (4)	0.0043 (4)
C42	0.0192 (5)	0.0184 (5)	0.0217 (5)	0.0023 (4)	0.0035 (4)	0.0029 (4)
C43	0.0175 (5)	0.0201 (5)	0.0187 (5)	0.0001 (4)	0.0016 (4)	0.0032 (4)
C44	0.0189 (5)	0.0237 (5)	0.0230 (5)	−0.0022 (4)	−0.0004 (4)	0.0071 (4)
C45	0.0173 (5)	0.0186 (5)	0.0239 (5)	−0.0006 (4)	0.0002 (4)	0.0034 (4)
O51	0.0310 (5)	0.0274 (4)	0.0418 (5)	−0.0139 (4)	−0.0146 (4)	0.0181 (4)
O52	0.0220 (4)	0.0224 (4)	0.0352 (5)	−0.0010 (3)	−0.0048 (3)	0.0089 (3)
O53	0.0186 (4)	0.0185 (4)	0.0348 (4)	−0.0030 (3)	−0.0032 (3)	0.0066 (3)
O54	0.0217 (4)	0.0230 (4)	0.0339 (4)	0.0021 (3)	−0.0014 (3)	0.0076 (3)
C51	0.0192 (5)	0.0166 (4)	0.0219 (5)	−0.0006 (4)	0.0023 (4)	0.0021 (4)
C52	0.0188 (5)	0.0168 (4)	0.0217 (5)	−0.0023 (4)	0.0004 (4)	0.0023 (4)
C53	0.0169 (5)	0.0162 (4)	0.0251 (5)	−0.0005 (4)	0.0006 (4)	0.0025 (4)
C54	0.0191 (5)	0.0163 (4)	0.0260 (5)	−0.0009 (4)	−0.0006 (4)	0.0035 (4)
C55	0.0179 (5)	0.0155 (4)	0.0246 (5)	0.0006 (4)	0.0019 (4)	−0.0001 (4)

Geometric parameters (Å, º)

N1—H1A	0.900 (16)	C33—H33A	0.997 (16)
N1—H1B	0.902 (18)	C33—H33B	1.018 (17)
N1—C1	1.3179 (15)	C33—C34	1.5220 (15)
N2—C1	1.3558 (14)	C34—H34A	0.970 (15)
N2—C2	1.3245 (17)	C34—H34B	1.001 (17)
N3—H3	0.994 (19)	C34—C35	1.5107 (15)
N3—C1	1.3623 (14)	O41—C41	1.2532 (13)
N3—C4	1.3484 (16)	O42—C41	1.2773 (13)
C2—H2	0.964 (16)	O43—C45	1.2517 (13)
C2—C3	1.4005 (18)	O44—C45	1.2753 (14)
C3—H3A	0.986 (16)	C41—C42	1.5100 (14)
C3—C4	1.3658 (17)	C42—H42A	0.991 (14)
C4—H4	0.964 (15)	C42—H42B	0.978 (16)
N21—H21A	0.873 (17)	C42—C43	1.5392 (15)
N21—H21B	0.917 (19)	C43—H43A	1.003 (14)
N21—C21	1.3219 (15)	C43—H43B	1.002 (15)
N22—H22	0.933 (19)	C43—C44	1.5217 (15)
N22—C21	1.3596 (14)	C44—H44A	0.994 (17)
N22—C22	1.3500 (15)	C44—H44B	0.988 (17)
N23—C21	1.3560 (14)	C44—C45	1.5119 (15)
N23—C24	1.3208 (15)	O51—H51	0.90 (2)
C22—H22A	0.986 (15)	O51—C51	1.3195 (13)
C22—C23	1.3616 (16)	O52—C51	1.2097 (14)
C23—H23	0.966 (16)	O53—H53	0.91 (2)
C23—C24	1.4037 (16)	O53—C55	1.3254 (13)
C24—H24	0.962 (15)	O54—C55	1.2111 (14)
O31—H31	0.94 (2)	C51—C52	1.5021 (15)
O31—C31	1.3231 (13)	C52—H52A	1.015 (15)
O32—C31	1.2133 (14)	C52—H52B	0.970 (15)
O33—H33	0.93 (2)	C52—C53	1.5200 (14)
O33—C35	1.3293 (13)	C53—H53A	0.983 (15)
O34—C35	1.2056 (14)	C53—H53B	0.985 (15)
C31—C32	1.5103 (15)	C53—C54	1.5162 (15)
C32—H32A	0.990 (17)	C54—H54A	0.982 (15)
C32—H32B	1.011 (16)	C54—H54B	0.998 (16)
C32—C33	1.5150 (15)	C54—C55	1.5054 (14)
H1A—N1—H1B	120.5 (15)	H34A—C34—H34B	105.8 (13)
C1—N1—H1A	120.4 (11)	C35—C34—C33	113.74 (10)
C1—N1—H1B	118.9 (11)	C35—C34—H34A	105.8 (9)
C2—N2—C1	117.28 (10)	C35—C34—H34B	107.3 (10)
C1—N3—H3	119.9 (11)	O33—C35—C34	112.42 (10)
C4—N3—H3	119.3 (11)	O34—C35—O33	123.14 (10)
C4—N3—C1	120.79 (10)	O34—C35—C34	124.44 (10)
N1—C1—N2	119.60 (10)	O41—C41—O42	122.31 (10)
N1—C1—N3	119.27 (10)	O41—C41—C42	120.32 (10)
N2—C1—N3	121.12 (11)	O42—C41—C42	117.30 (9)
N2—C2—H2	116.5 (10)	C41—C42—H42A	108.7 (8)
N2—C2—C3	124.25 (11)	C41—C42—H42B	109.3 (9)
C3—C2—H2	119.3 (10)	C41—C42—C43	110.42 (8)
C2—C3—H3A	122.9 (9)	H42A—C42—H42B	110.0 (12)
C4—C3—C2	116.26 (12)	C43—C42—H42A	109.3 (8)
C4—C3—H3A	120.8 (9)	C43—C42—H42B	109.1 (9)
N3—C4—C3	120.29 (11)	C42—C43—H43A	108.9 (8)
N3—C4—H4	114.5 (9)	C42—C43—H43B	109.9 (8)
C3—C4—H4	125.2 (9)	H43A—C43—H43B	106.1 (12)
H21A—N21—H21B	119.1 (16)	C44—C43—C42	111.55 (8)
C21—N21—H21A	121.5 (11)	C44—C43—H43A	111.0 (8)
C21—N21—H21B	119.3 (12)	C44—C43—H43B	109.2 (9)
C21—N22—H22	120.2 (11)	C43—C44—H44A	110.7 (10)
C22—N22—H22	118.8 (11)	C43—C44—H44B	113.9 (10)
C22—N22—C21	121.03 (10)	H44A—C44—H44B	106.0 (14)
C24—N23—C21	117.21 (9)	C45—C44—C43	115.21 (9)
N21—C21—N22	119.32 (10)	C45—C44—H44A	107.3 (10)
N21—C21—N23	119.66 (10)	C45—C44—H44B	102.9 (10)
N23—C21—N22	121.02 (10)	O43—C45—O44	121.71 (10)
N22—C22—H22A	115.0 (9)	O43—C45—C44	120.91 (10)
N22—C22—C23	120.12 (10)	O44—C45—C44	117.37 (9)
C23—C22—H22A	124.8 (9)	C51—O51—H51	108.7 (13)
C22—C23—H23	122.5 (9)	C55—O53—H53	113.5 (13)
C22—C23—C24	116.21 (11)	O51—C51—C52	112.22 (9)
C24—C23—H23	121.3 (9)	O52—C51—O51	123.03 (10)
N23—C24—C23	124.39 (11)	O52—C51—C52	124.75 (9)
N23—C24—H24	114.9 (9)	C51—C52—H52A	106.5 (9)
C23—C24—H24	120.7 (9)	C51—C52—H52B	107.5 (9)
C31—O31—H31	111.7 (12)	C51—C52—C53	114.20 (9)
C35—O33—H33	107.4 (12)	H52A—C52—H52B	107.8 (12)
O31—C31—C32	111.24 (9)	C53—C52—H52A	109.5 (9)
O32—C31—O31	123.73 (10)	C53—C52—H52B	111.1 (9)
O32—C31—C32	125.03 (10)	C52—C53—H53A	109.8 (9)
C31—C32—H32A	107.6 (10)	C52—C53—H53B	109.9 (9)
C31—C32—H32B	106.2 (9)	H53A—C53—H53B	109.1 (12)
C31—C32—C33	114.65 (10)	C54—C53—C52	108.98 (9)
H32A—C32—H32B	103.5 (13)	C54—C53—H53A	110.2 (9)
C33—C32—H32A	112.1 (10)	C54—C53—H53B	108.9 (9)
C33—C32—H32B	112.0 (9)	C53—C54—H54A	110.1 (9)
C32—C33—H33A	108.6 (9)	C53—C54—H54B	109.4 (9)
C32—C33—H33B	110.1 (9)	H54A—C54—H54B	108.6 (13)
C32—C33—C34	111.02 (10)	C55—C54—C53	115.86 (9)
H33A—C33—H33B	108.3 (13)	C55—C54—H54A	106.4 (9)
C34—C33—H33A	110.2 (9)	C55—C54—H54B	106.1 (9)
C34—C33—H33B	108.6 (10)	O53—C55—C54	109.69 (9)
C33—C34—H34A	112.8 (9)	O54—C55—O53	124.34 (10)
C33—C34—H34B	110.9 (10)	O54—C55—C54	125.97 (10)
N2—C2—C3—C4	0.8 (2)	O32—C31—C32—C33	−0.26 (17)
C1—N2—C2—C3	−0.92 (19)	C31—C32—C33—C34	−177.34 (9)
C1—N3—C4—C3	−0.48 (17)	C32—C33—C34—C35	−177.82 (10)
C2—N2—C1—N1	−178.35 (11)	C33—C34—C35—O33	173.73 (10)
C2—N2—C1—N3	0.30 (16)	C33—C34—C35—O34	−5.45 (17)
C2—C3—C4—N3	−0.09 (18)	O41—C41—C42—C43	105.43 (11)
C4—N3—C1—N1	179.04 (10)	O42—C41—C42—C43	−71.56 (12)
C4—N3—C1—N2	0.39 (16)	C41—C42—C43—C44	−65.71 (12)
N22—C22—C23—C24	−0.37 (16)	C42—C43—C44—C45	−169.11 (9)
C21—N22—C22—C23	0.46 (16)	C43—C44—C45—O43	−26.06 (16)
C21—N23—C24—C23	−0.49 (17)	C43—C44—C45—O44	155.25 (10)
C22—N22—C21—N21	179.02 (10)	O51—C51—C52—C53	176.30 (10)
C22—N22—C21—N23	−0.56 (16)	O52—C51—C52—C53	−3.27 (16)
C22—C23—C24—N23	0.41 (17)	C51—C52—C53—C54	−174.19 (9)
C24—N23—C21—N21	−179.03 (10)	C52—C53—C54—C55	−179.96 (9)
C24—N23—C21—N22	0.55 (15)	C53—C54—C55—O53	−174.00 (9)
O31—C31—C32—C33	180.00 (10)	C53—C54—C55—O54	5.96 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···N2^i	0.902 (18)	2.196 (18)	3.0918 (14)	172.3 (15)
N1—H1A···O41^ii	0.900 (16)	1.942 (16)	2.8315 (13)	169.4 (15)
N3—H3···O42^ii	0.994 (19)	1.618 (19)	2.6022 (12)	170.2 (17)
N21—H21A···O43	0.873 (17)	2.066 (17)	2.9240 (13)	167.4 (15)
N21—H21B···N23^iii	0.917 (19)	2.190 (19)	3.1049 (14)	174.9 (16)
N22—H22···O44	0.933 (19)	1.660 (19)	2.5853 (12)	170.7 (17)
O31—H31···O42^iv	0.94 (2)	1.68 (2)	2.6094 (11)	169.6 (19)
O33—H33···O41^v	0.93 (2)	1.67 (2)	2.6003 (12)	173 (2)
O51—H51···O43^iv	0.90 (2)	1.69 (2)	2.5899 (12)	175 (2)
O53—H53···O44^v	0.91 (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) x−1, y−1, z; (v) x+1, y, z.