The effect of amino acid backbone length on mol­ecular packing: crystalline tartrates of glycine, β-alanine, γ-amino­butyric acid (GABA) and DL-α-amino­butyric acid (AABA)

We report a novel 1:1 cocrystal of β-alanine with DL-tartaric acid, C₃H₇NO₂·C₄H₆O₆, (II), and three new mol­ecular salts of DL-tartaric acid with β-alanine {3-aza­niumyl­propanoic acid–3-aza­niumyl­propano­ate DL-tartaric acid–DL-tartrate, [H(C₃H₇NO₂)₂]⁺·[H(C₄H₅O₆)₂]⁻, (III)}, γ-amino­butyric acid [3-carb­oxy­pro­pan­aminium DL-tartrate, C₄H₁₀NO₂⁺·C₄H₅O₆⁻, (IV)] and DL-α-amino­butyric acid {DL-2-aza­niumyl­butanoic acid–DL-2-aza­niumyl­butano­ate DL-tartaric acid–DL-tartrate, [H(C₄H₉NO₂)₂]⁺·[H(C₄H₅O₆)₂]⁻, (V)}. The crystal structures of binary crystals of DL-tartaric acid with glycine, (I), β-alanine, (II) and (III), GABA, (IV), and DL-AABA, (V), have similar mol­ecular packing and crystallographic motifs. The shortest amino acid (i.e. glycine) forms a cocrystal, (I), with DL-tartaric acid, whereas the larger amino acids form mol­ecular salts, viz. (IV) and (V). β-Alanine is the only amino acid capable of forming both a cocrystal [i.e. (II)] and a mol­ecular salt [i.e. (III)] with DL-tartaric acid. The cocrystals of glycine and β-alanine with DL-tartaric acid, i.e. (I) and (II), respectively, contain chains of amino acid zwitterions, similar to the structure of pure glycine. In the structures of the mol­ecular salts of amino acids, the amino acid cations form isolated dimers [of β-alanine in (III), GABA in (IV) and DL-AABA in (V)], which are linked by strong O—H...O hydrogen bonds. Moreover, the three crystal structures comprise different types of dimeric cations, i.e. (A...A)⁺ in (III) and (V), and A⁺...A⁺ in (IV). Mol­ecular salts (IV) and (V) are the first examples of mol­ecular salts of GABA and DL-AABA that contain dimers of amino acid cations. The geometry of each investigated amino acid (except DL-AABA) correlates with the melting point of its mixed crystal.

Computing details

For all structures, data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for beta-ala_DL-tart_II; SHELXS (Sheldrick, 2008) for beta-ala_DL-tart_III; SHELXT (Sheldrick, 2015a) for DL-AABA_DL-tart_V. For all structures, program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

β-Alanine–DL-tartaric acid (1/1) (beta-ala_DL-tart_II)

Crystal data

C3H7NO2·C4H6O6	F(000) = 504
Mr = 239.18	Dx = 1.626 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 4.88596 (17) Å	Cell parameters from 4805 reflections
b = 9.4420 (2) Å	θ = 1.9–27.7°
c = 21.7319 (6) Å	µ = 0.15 mm^−1
β = 103.021 (3)°	T = 293 K
V = 976.78 (5) Å^3	Block, colourless
Z = 4	0.86 × 0.12 × 0.08 mm

Data collection

Agilent Xcalibur Ruby Gemini ultra diffractometer	1996 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1889 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 10.3457 pixels mm^-1	θmax = 26.4°, θmin = 1.9°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −11→11
Tmin = 0.791, Tmax = 1.000	l = −27→27
12471 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.027	H-atom parameters constrained
wR(F^2) = 0.072	w = 1/[σ^2(Fo^2) + (0.0381P)^2 + 0.1523P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1996 reflections	Δρmax = 0.21 e Å^−3
151 parameters	Δρmin = −0.17 e Å^−3
0 restraints

Special details

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

Refinement. Refined as a 2-component twin.

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

	x	y	z	Uiso*/Ueq
O4	0.2841 (2)	0.64658 (11)	0.00115 (6)	0.0347 (3)
H4	0.366835	0.584657	0.024619	0.042*
O3	0.7265 (2)	0.61737 (11)	−0.06679 (5)	0.0292 (2)
H3	0.891706	0.628304	−0.048873	0.035*
O6	0.8728 (3)	0.87259 (11)	0.05260 (5)	0.0376 (3)
H6	0.996236	0.876041	0.085139	0.045*
O1	0.1750 (3)	0.86171 (12)	−0.11791 (5)	0.0400 (3)
H1	0.044420	0.864370	−0.149112	0.048*
C4	0.7182 (3)	0.76069 (15)	0.05370 (6)	0.0257 (3)
C3	0.4722 (3)	0.75774 (15)	−0.00302 (7)	0.0250 (3)
H3A	0.370268	0.847456	−0.004176	0.030*
O5	0.7605 (3)	0.66850 (13)	0.09322 (5)	0.0406 (3)
O7	0.7307 (2)	0.58365 (11)	0.30080 (5)	0.0311 (3)
O8	0.7092 (3)	0.38062 (11)	0.35126 (5)	0.0401 (3)
O2	0.2879 (2)	0.66539 (11)	−0.16318 (5)	0.0333 (3)
C2	0.5776 (3)	0.74545 (14)	−0.06436 (6)	0.0227 (3)
H2	0.702772	0.825350	−0.066754	0.027*
C5	0.6129 (3)	0.46909 (14)	0.30895 (6)	0.0236 (3)
C1	0.3293 (3)	0.75113 (14)	−0.12109 (7)	0.0229 (3)
C6	0.3351 (3)	0.43399 (15)	0.26446 (7)	0.0252 (3)
H6A	0.361525	0.352096	0.239470	0.030*
H6B	0.201323	0.407929	0.289377	0.030*
N1	0.3915 (3)	0.58754 (13)	0.17552 (6)	0.0334 (3)
H1A	0.325984	0.664811	0.153656	0.050*
H1B	0.390468	0.515443	0.149088	0.050*
H1C	0.566431	0.603181	0.197164	0.050*
C7	0.2106 (3)	0.55276 (16)	0.22007 (7)	0.0269 (3)
H7A	0.025827	0.524954	0.196286	0.032*
H7B	0.188929	0.636301	0.244517	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0258 (6)	0.0374 (6)	0.0372 (6)	−0.0056 (5)	−0.0006 (5)	0.0099 (5)
O3	0.0207 (5)	0.0295 (5)	0.0336 (6)	0.0058 (4)	−0.0016 (5)	−0.0020 (4)
O6	0.0412 (7)	0.0329 (6)	0.0307 (6)	−0.0072 (5)	−0.0088 (5)	−0.0021 (5)
O1	0.0421 (7)	0.0389 (6)	0.0300 (6)	0.0191 (6)	−0.0107 (5)	−0.0073 (5)
C4	0.0262 (8)	0.0275 (7)	0.0221 (7)	0.0022 (6)	0.0028 (6)	−0.0025 (6)
C3	0.0233 (7)	0.0250 (7)	0.0247 (7)	−0.0005 (6)	0.0012 (6)	0.0003 (6)
O5	0.0439 (7)	0.0447 (7)	0.0285 (6)	−0.0035 (6)	−0.0019 (5)	0.0113 (5)
O7	0.0262 (6)	0.0301 (5)	0.0317 (6)	−0.0083 (4)	−0.0046 (5)	0.0018 (5)
O8	0.0394 (7)	0.0309 (6)	0.0386 (6)	−0.0017 (5)	−0.0153 (6)	0.0095 (5)
O2	0.0324 (6)	0.0318 (6)	0.0304 (6)	0.0031 (5)	−0.0042 (5)	−0.0077 (5)
C2	0.0214 (8)	0.0211 (6)	0.0236 (7)	−0.0004 (5)	0.0007 (6)	−0.0005 (5)
C5	0.0228 (7)	0.0225 (6)	0.0231 (7)	0.0026 (6)	−0.0001 (6)	−0.0032 (5)
C1	0.0226 (8)	0.0221 (7)	0.0226 (7)	−0.0001 (6)	0.0021 (6)	0.0022 (5)
C6	0.0236 (7)	0.0253 (7)	0.0240 (7)	−0.0025 (6)	−0.0003 (6)	0.0020 (6)
N1	0.0447 (9)	0.0279 (6)	0.0291 (7)	0.0077 (6)	0.0117 (6)	0.0038 (5)
C7	0.0218 (7)	0.0302 (8)	0.0260 (8)	0.0005 (6)	−0.0005 (6)	0.0007 (6)

Geometric parameters (Å, º)

O4—H4	0.8200	O2—C1	1.2041 (17)
O4—C3	1.4112 (18)	C2—H2	0.9800
O3—H3	0.8200	C2—C1	1.5231 (19)
O3—C2	1.4185 (17)	C5—C6	1.515 (2)
O6—H6	0.8200	C6—H6A	0.9700
O6—C4	1.3024 (18)	C6—H6B	0.9700
O1—H1	0.8200	C6—C7	1.515 (2)
O1—C1	1.2990 (17)	N1—H1A	0.8900
C4—C3	1.516 (2)	N1—H1B	0.8900
C4—O5	1.2075 (17)	N1—H1C	0.8900
C3—H3A	0.9800	N1—C7	1.487 (2)
C3—C2	1.5381 (19)	C7—H7A	0.9700
O7—C5	1.2564 (17)	C7—H7B	0.9700
O8—C5	1.2528 (17)
C3—O4—H4	109.5	O1—C1—C2	110.56 (12)
C2—O3—H3	109.5	O2—C1—O1	125.49 (14)
C4—O6—H6	109.5	O2—C1—C2	123.93 (13)
C1—O1—H1	109.5	C5—C6—H6A	108.6
O6—C4—C3	110.93 (12)	C5—C6—H6B	108.6
O5—C4—O6	126.21 (14)	H6A—C6—H6B	107.6
O5—C4—C3	122.86 (13)	C7—C6—C5	114.71 (12)
O4—C3—C4	111.72 (12)	C7—C6—H6A	108.6
O4—C3—H3A	108.1	C7—C6—H6B	108.6
O4—C3—C2	110.46 (12)	H1A—N1—H1B	109.5
C4—C3—H3A	108.1	H1A—N1—H1C	109.5
C4—C3—C2	110.32 (12)	H1B—N1—H1C	109.5
C2—C3—H3A	108.1	C7—N1—H1A	109.5
O3—C2—C3	111.79 (11)	C7—N1—H1B	109.5
O3—C2—H2	108.8	C7—N1—H1C	109.5
O3—C2—C1	108.75 (11)	C6—C7—H7A	109.3
C3—C2—H2	108.8	C6—C7—H7B	109.3
C1—C2—C3	109.74 (11)	N1—C7—C6	111.44 (12)
C1—C2—H2	108.8	N1—C7—H7A	109.3
O7—C5—C6	118.12 (12)	N1—C7—H7B	109.3
O8—C5—O7	124.70 (13)	H7A—C7—H7B	108.0
O8—C5—C6	117.18 (12)
O4—C3—C2—O3	−61.53 (15)	C3—C2—C1—O1	52.44 (15)
O4—C3—C2—C1	59.22 (14)	C3—C2—C1—O2	−128.76 (15)
O3—C2—C1—O1	175.01 (13)	O5—C4—C3—O4	8.0 (2)
O3—C2—C1—O2	−6.18 (19)	O5—C4—C3—C2	−115.30 (16)
O6—C4—C3—O4	−173.00 (13)	O7—C5—C6—C7	−8.10 (19)
O6—C4—C3—C2	63.73 (15)	O8—C5—C6—C7	172.23 (14)
C4—C3—C2—O3	62.47 (14)	C5—C6—C7—N1	64.50 (16)
C4—C3—C2—C1	−176.77 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3^i	0.82	2.21	2.8778 (15)	139
O3—H3···O4^ii	0.82	1.99	2.8048 (15)	175
O6—H6···O8^iii	0.82	1.76	2.5728 (15)	173
O1—H1···O7^iv	0.82	1.74	2.5240 (16)	160
N1—H1A···O8^v	0.89	2.05	2.8477 (17)	149
N1—H1C···O7	0.89	2.22	2.8508 (17)	127

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

3-Azaniumylpropanoic acid–3-azaniumylpropanoate DL-tartaric acid–DL-tartrate (beta-ala_DL-tart_III)

Crystal data

C6H15N2O4^+·C8H11O12^−	Z = 1
Mr = 478.37	F(000) = 252
Triclinic, P1	Dx = 1.655 Mg m^−3
a = 4.9216 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.5949 (6) Å	Cell parameters from 2996 reflections
c = 12.1187 (7) Å	θ = 1.8–27.8°
α = 108.610 (6)°	µ = 0.15 mm^−1
β = 97.243 (5)°	T = 293 K
γ = 92.752 (5)°	Block, colourless
V = 479.82 (6) Å^3	0.3 × 0.14 × 0.12 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	1962 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1626 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 10.3457 pixels mm^-1	θmax = 26.4°, θmin = 1.8°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −10→10
Tmin = 0.965, Tmax = 1.000	l = −15→15
6002 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0499P)^2 + 0.2341P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
1962 reflections	Δρmax = 0.25 e Å^−3
154 parameters	Δρmin = −0.27 e Å^−3
0 restraints

Special details

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

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

	x	y	z	Uiso*/Ueq
O3	0.2694 (3)	0.99355 (16)	0.13191 (12)	0.0259 (3)
O6	0.1929 (3)	0.59451 (15)	0.06566 (11)	0.0291 (3)
O4	0.7460 (2)	0.84652 (15)	0.02993 (11)	0.0265 (3)
H4	0.901138	0.877581	0.066836	0.032*
O1	0.8831 (3)	0.97686 (15)	0.31713 (11)	0.0294 (3)
H1	0.998520	1.049321	0.361066	0.035*
O5	0.3221 (3)	0.63581 (17)	−0.09339 (11)	0.0332 (3)
O8	0.4355 (3)	0.85520 (15)	0.44061 (12)	0.0337 (3)
O2	0.6977 (3)	1.18792 (16)	0.27615 (14)	0.0404 (4)
C3	0.5851 (3)	0.77953 (19)	0.09600 (14)	0.0188 (4)
H3A	0.701002	0.719059	0.136726	0.023*
C2	0.4658 (3)	0.91587 (19)	0.18716 (14)	0.0194 (4)
H2	0.373911	0.866092	0.236630	0.023*
N1	0.2081 (3)	0.36309 (18)	0.23089 (14)	0.0285 (4)
H1A	0.314904	0.365175	0.177231	0.043*
H1B	0.033510	0.338485	0.196660	0.043*
H1C	0.257938	0.287190	0.263126	0.043*
O7	0.7675 (3)	0.77751 (18)	0.54905 (14)	0.0481 (4)
C5	0.5866 (4)	0.7502 (2)	0.46338 (16)	0.0260 (4)
C1	0.6937 (3)	1.0436 (2)	0.26560 (14)	0.0213 (4)
C4	0.3501 (3)	0.6606 (2)	0.01279 (15)	0.0202 (4)
C7	0.2382 (4)	0.5271 (2)	0.32363 (16)	0.0263 (4)
H7A	0.136349	0.522122	0.386131	0.032*
H7B	0.162704	0.607591	0.290620	0.032*
C6	0.5368 (4)	0.5792 (2)	0.37317 (17)	0.0288 (4)
H6A	0.638730	0.575852	0.309083	0.035*
H6B	0.607583	0.500798	0.409362	0.035*
H6	0.000000	0.500000	0.000000	0.091 (15)*
H8	0.500000	1.000000	0.500000	0.122 (19)*
H3	0.319 (7)	1.027 (4)	0.086 (3)	0.093 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0200 (6)	0.0286 (7)	0.0282 (7)	0.0037 (5)	−0.0019 (5)	0.0100 (6)
O6	0.0252 (7)	0.0309 (7)	0.0275 (7)	−0.0118 (5)	−0.0017 (5)	0.0086 (6)
O4	0.0186 (6)	0.0319 (7)	0.0278 (7)	−0.0072 (5)	0.0034 (5)	0.0092 (5)
O1	0.0245 (7)	0.0267 (7)	0.0295 (7)	−0.0029 (5)	−0.0103 (5)	0.0050 (5)
O5	0.0260 (7)	0.0457 (8)	0.0215 (7)	−0.0083 (6)	−0.0025 (5)	0.0062 (6)
O8	0.0428 (8)	0.0224 (7)	0.0303 (7)	0.0035 (6)	−0.0040 (6)	0.0044 (6)
O2	0.0362 (8)	0.0218 (7)	0.0553 (10)	−0.0054 (6)	−0.0131 (7)	0.0102 (6)
C3	0.0156 (8)	0.0189 (8)	0.0216 (8)	−0.0020 (6)	−0.0008 (6)	0.0078 (6)
C2	0.0175 (8)	0.0194 (8)	0.0202 (8)	−0.0014 (6)	−0.0010 (6)	0.0067 (6)
N1	0.0238 (8)	0.0234 (8)	0.0306 (8)	−0.0019 (6)	−0.0038 (6)	0.0017 (6)
O7	0.0507 (9)	0.0316 (8)	0.0470 (9)	−0.0099 (7)	−0.0270 (7)	0.0068 (7)
C5	0.0253 (9)	0.0241 (9)	0.0256 (9)	−0.0053 (7)	−0.0013 (7)	0.0069 (7)
C1	0.0191 (8)	0.0234 (9)	0.0187 (8)	−0.0010 (7)	0.0002 (7)	0.0047 (7)
C4	0.0162 (8)	0.0185 (8)	0.0237 (9)	0.0010 (6)	−0.0003 (6)	0.0051 (7)
C7	0.0219 (9)	0.0232 (9)	0.0264 (9)	0.0016 (7)	−0.0007 (7)	−0.0004 (7)
C6	0.0228 (9)	0.0256 (9)	0.0315 (10)	0.0006 (7)	−0.0016 (8)	0.0027 (8)

Geometric parameters (Å, º)

O3—C2	1.419 (2)	C3—C4	1.528 (2)
O3—H3	0.76 (3)	C2—H2	0.9800
O6—C4	1.283 (2)	C2—C1	1.521 (2)
O6—H6	1.2317 (11)	N1—H1A	0.8900
O4—H4	0.8200	N1—H1B	0.8900
O4—C3	1.4178 (19)	N1—H1C	0.8900
O1—H1	0.8200	N1—C7	1.483 (2)
O1—C1	1.312 (2)	O7—C5	1.232 (2)
O5—C4	1.224 (2)	C5—C6	1.512 (2)
O8—C5	1.271 (2)	C7—H7A	0.9700
O8—H8	1.2249 (12)	C7—H7B	0.9700
O2—C1	1.204 (2)	C7—C6	1.505 (2)
C3—H3A	0.9800	C6—H6A	0.9700
C3—C2	1.530 (2)	C6—H6B	0.9700
C2—O3—H3	115 (3)	C7—N1—H1C	109.5
C4—O6—H6	114.32 (12)	O8—C5—C6	114.91 (16)
C3—O4—H4	109.5	O7—C5—O8	125.87 (17)
C1—O1—H1	109.5	O7—C5—C6	119.21 (17)
C5—O8—H8	116.71 (13)	O1—C1—C2	111.95 (14)
O4—C3—H3A	109.1	O2—C1—O1	125.10 (15)
O4—C3—C2	110.97 (13)	O2—C1—C2	122.94 (16)
O4—C3—C4	109.37 (13)	O6—C4—C3	113.48 (14)
C2—C3—H3A	109.1	O5—C4—O6	125.53 (15)
C4—C3—H3A	109.1	O5—C4—C3	120.98 (15)
C4—C3—C2	109.30 (13)	N1—C7—H7A	109.6
O3—C2—C3	111.15 (13)	N1—C7—H7B	109.6
O3—C2—H2	108.4	N1—C7—C6	110.22 (15)
O3—C2—C1	109.77 (13)	H7A—C7—H7B	108.1
C3—C2—H2	108.4	C6—C7—H7A	109.6
C1—C2—C3	110.57 (13)	C6—C7—H7B	109.6
C1—C2—H2	108.4	C5—C6—H6A	108.9
H1A—N1—H1B	109.5	C5—C6—H6B	108.9
H1A—N1—H1C	109.5	C7—C6—C5	113.50 (15)
H1B—N1—H1C	109.5	C7—C6—H6A	108.9
C7—N1—H1A	109.5	C7—C6—H6B	108.9
C7—N1—H1B	109.5	H6A—C6—H6B	107.7
O3—C2—C1—O1	−178.92 (14)	C3—C2—C1—O2	122.88 (19)
O3—C2—C1—O2	−0.1 (2)	C2—C3—C4—O6	−58.10 (18)
O4—C3—C2—O3	67.20 (16)	C2—C3—C4—O5	121.42 (17)
O4—C3—C2—C1	−54.98 (18)	N1—C7—C6—C5	176.51 (15)
O4—C3—C4—O6	−179.77 (14)	O7—C5—C6—C7	143.16 (19)
O4—C3—C4—O5	−0.2 (2)	C4—C3—C2—O3	−53.49 (17)
O8—C5—C6—C7	−38.2 (2)	C4—C3—C2—C1	−175.68 (13)
C3—C2—C1—O1	−55.93 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3^i	0.82	1.97	2.7653 (17)	165
O1—H1···O7^ii	0.82	1.79	2.6092 (18)	174
N1—H1A···O4^iii	0.89	2.56	3.142 (2)	124
N1—H1A···O5^iii	0.89	2.16	3.017 (2)	161
N1—H1B···O5^iv	0.89	2.08	2.916 (2)	155
N1—H1B···O2^v	0.89	2.52	3.064 (2)	121
N1—H1C···O2^vi	0.89	2.37	2.986 (2)	127
O6—H6···O6^iv	1.23	1.23	2.464 (2)	180
O8—H8···O8^vii	1.22	1.22	2.4498 (19)	180

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

3-Carboxypropanaminium DL-tartrate (GABA_DL-tart_IV)

Crystal data

C4H10NO2^+·C4H5O6^−	Z = 4
Mr = 253.21	F(000) = 536
Triclinic, P1	Dx = 1.531 Mg m^−3
a = 9.5645 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.6521 (7) Å	Cell parameters from 3135 reflections
c = 14.3793 (8) Å	θ = 2.5–27.9°
α = 100.043 (6)°	µ = 0.14 mm^−1
β = 99.159 (6)°	T = 293 K
γ = 118.841 (8)°	Block, colourless
V = 1098.50 (16) Å^3	0.50 × 0.19 × 0.04 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	4471 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3662 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 10.3457 pixels mm^-1	θmax = 26.4°, θmin = 2.5°
ω scans	h = −11→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −11→12
Tmin = 0.837, Tmax = 1.000	l = −16→17
7048 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.121	w = 1/[σ^2(Fo^2) + (0.0573P)^2 + 0.3075P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
4471 reflections	Δρmax = 0.34 e Å^−3
317 parameters	Δρmin = −0.43 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
O27	0.2335 (2)	0.3689 (2)	0.92438 (10)	0.0559 (5)
H27	0.234925	0.453119	0.948700	0.067*
O28	0.3116 (3)	0.2105 (2)	0.97021 (11)	0.0611 (5)
N21	0.15229 (19)	0.48352 (18)	1.29836 (11)	0.0315 (3)
H21A	0.081446	0.505581	1.266198	0.047*
H21B	0.201127	0.551880	1.359302	0.047*
H21C	0.097334	0.379626	1.300724	0.047*
C25	0.2971 (2)	0.3285 (2)	0.99280 (13)	0.0333 (4)
C26	0.3525 (2)	0.4299 (2)	1.09787 (13)	0.0343 (4)
H26A	0.416804	0.546062	1.101709	0.041*
H26B	0.424871	0.404818	1.137152	0.041*
C27	0.2082 (2)	0.3992 (2)	1.14145 (12)	0.0287 (4)
H27A	0.136324	0.426941	1.104287	0.034*
H27B	0.142897	0.283547	1.138669	0.034*
C28	0.2799 (2)	0.5059 (2)	1.24674 (13)	0.0331 (4)
H28A	0.355721	0.480358	1.281845	0.040*
H28B	0.343526	0.620878	1.247988	0.040*
O17	0.2916 (2)	0.78703 (18)	0.89978 (11)	0.0528 (4)
H17	0.288267	0.707847	0.865098	0.063*
O18	0.2343 (3)	0.63217 (19)	1.00016 (12)	0.0670 (6)
N11	0.18466 (18)	0.96254 (17)	1.30101 (11)	0.0300 (3)
H11A	0.099736	0.860186	1.290229	0.045*
H11B	0.161938	1.034584	1.331430	0.045*
H11C	0.276063	0.975514	1.338566	0.045*
C15	0.2619 (2)	0.7581 (2)	0.98005 (13)	0.0322 (4)
C16	0.2598 (3)	0.8926 (2)	1.04874 (14)	0.0396 (5)
H16A	0.172193	0.906233	1.016206	0.048*
H16B	0.364693	0.995464	1.061857	0.048*
C17	0.2329 (2)	0.8619 (2)	1.14583 (13)	0.0322 (4)
H17A	0.134656	0.753652	1.133485	0.039*
H17B	0.327482	0.862586	1.182886	0.039*
C18	0.2117 (3)	0.9914 (2)	1.20568 (14)	0.0347 (4)
H18A	0.310174	1.099484	1.217999	0.042*
H18B	0.117522	0.990906	1.168334	0.042*
O21	0.45891 (15)	0.33231 (15)	0.54409 (9)	0.0289 (3)
H21	0.469131	0.270225	0.502773	0.035*
O22	0.24110 (16)	0.26931 (16)	0.42271 (9)	0.0343 (3)
O23	0.17396 (15)	0.46887 (14)	0.53599 (9)	0.0277 (3)
H23	0.101937	0.386506	0.491266	0.033*
O24	0.08990 (14)	0.18626 (13)	0.61368 (9)	0.0278 (3)
H24	0.118448	0.120257	0.597192	0.033*
O25	0.05168 (15)	0.38627 (15)	0.74327 (9)	0.0305 (3)
O26	0.31479 (15)	0.59350 (14)	0.77576 (9)	0.0313 (3)
C21	0.3294 (2)	0.33719 (19)	0.50715 (12)	0.0215 (3)
C22	0.2927 (2)	0.43689 (19)	0.58254 (12)	0.0211 (3)
H22	0.396102	0.542966	0.616712	0.025*
C23	0.23280 (19)	0.34588 (19)	0.65918 (12)	0.0218 (3)
H23A	0.321942	0.335473	0.694751	0.026*
C24	0.1933 (2)	0.4480 (2)	0.73227 (11)	0.0224 (3)
O11	0.67246 (17)	−0.09112 (15)	0.20349 (10)	0.0416 (4)
H11	0.693006	−0.127099	0.154893	0.050*
O12	0.93554 (16)	0.11821 (16)	0.24006 (10)	0.0373 (3)
O13	0.89270 (14)	0.30379 (13)	0.37845 (9)	0.0265 (3)
H13	0.863097	0.367061	0.399222	0.032*
O14	0.80716 (15)	0.02295 (15)	0.45153 (9)	0.0296 (3)
H14	0.869032	0.102185	0.500402	0.035*
O15	0.71741 (16)	0.20586 (15)	0.55839 (9)	0.0335 (3)
O16	0.51851 (14)	0.15786 (14)	0.42978 (9)	0.0287 (3)
C11	0.7995 (2)	0.0580 (2)	0.25300 (12)	0.0259 (4)
C12	0.75111 (19)	0.14582 (19)	0.32773 (12)	0.0224 (3)
H12	0.663850	0.159266	0.292717	0.027*
C13	0.6861 (2)	0.04870 (19)	0.40067 (12)	0.0218 (3)
H13A	0.586340	−0.058992	0.364098	0.026*
C14	0.6386 (2)	0.14525 (19)	0.47132 (12)	0.0219 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O27	0.1109 (14)	0.0599 (10)	0.0257 (7)	0.0668 (10)	0.0182 (8)	0.0108 (7)
O28	0.1201 (15)	0.0574 (10)	0.0379 (8)	0.0673 (11)	0.0296 (9)	0.0155 (7)
N21	0.0350 (8)	0.0316 (8)	0.0281 (8)	0.0166 (7)	0.0165 (7)	0.0050 (6)
C25	0.0484 (11)	0.0333 (10)	0.0278 (9)	0.0250 (9)	0.0198 (9)	0.0115 (8)
C26	0.0341 (10)	0.0454 (11)	0.0249 (9)	0.0226 (9)	0.0115 (8)	0.0051 (8)
C27	0.0299 (9)	0.0312 (9)	0.0236 (9)	0.0154 (8)	0.0095 (7)	0.0054 (7)
C28	0.0267 (9)	0.0421 (11)	0.0254 (9)	0.0155 (8)	0.0113 (8)	0.0024 (8)
O17	0.1020 (13)	0.0450 (9)	0.0354 (8)	0.0490 (9)	0.0381 (9)	0.0166 (7)
O18	0.1423 (17)	0.0533 (10)	0.0511 (10)	0.0712 (11)	0.0570 (11)	0.0296 (8)
N11	0.0324 (8)	0.0296 (8)	0.0272 (8)	0.0159 (7)	0.0131 (6)	0.0032 (6)
C15	0.0437 (11)	0.0312 (9)	0.0297 (10)	0.0236 (9)	0.0165 (8)	0.0092 (8)
C16	0.0651 (14)	0.0327 (10)	0.0344 (11)	0.0313 (10)	0.0267 (10)	0.0115 (8)
C17	0.0448 (11)	0.0334 (10)	0.0285 (9)	0.0259 (9)	0.0170 (8)	0.0091 (8)
C18	0.0498 (12)	0.0331 (10)	0.0312 (10)	0.0264 (9)	0.0205 (9)	0.0094 (8)
O21	0.0315 (7)	0.0365 (7)	0.0247 (6)	0.0249 (6)	0.0074 (5)	0.0008 (5)
O22	0.0416 (7)	0.0415 (7)	0.0228 (6)	0.0291 (6)	0.0034 (6)	−0.0012 (5)
O23	0.0343 (7)	0.0292 (6)	0.0258 (6)	0.0238 (6)	0.0051 (5)	0.0035 (5)
O24	0.0285 (6)	0.0223 (6)	0.0350 (7)	0.0161 (5)	0.0118 (5)	0.0029 (5)
O25	0.0305 (7)	0.0343 (7)	0.0317 (7)	0.0202 (6)	0.0141 (5)	0.0061 (5)
O26	0.0325 (7)	0.0288 (7)	0.0254 (6)	0.0130 (6)	0.0097 (5)	−0.0007 (5)
C21	0.0243 (8)	0.0206 (8)	0.0212 (8)	0.0128 (7)	0.0088 (7)	0.0047 (6)
C22	0.0242 (8)	0.0224 (8)	0.0212 (8)	0.0160 (7)	0.0074 (7)	0.0036 (6)
C23	0.0223 (8)	0.0243 (8)	0.0219 (8)	0.0155 (7)	0.0059 (7)	0.0042 (6)
C24	0.0295 (9)	0.0293 (9)	0.0153 (7)	0.0199 (7)	0.0084 (7)	0.0068 (6)
O11	0.0441 (8)	0.0315 (7)	0.0363 (8)	0.0132 (6)	0.0189 (6)	−0.0057 (6)
O12	0.0338 (7)	0.0406 (7)	0.0393 (8)	0.0210 (6)	0.0189 (6)	0.0030 (6)
O13	0.0267 (6)	0.0206 (6)	0.0334 (7)	0.0141 (5)	0.0121 (5)	0.0022 (5)
O14	0.0351 (7)	0.0299 (6)	0.0301 (7)	0.0244 (6)	0.0052 (5)	0.0041 (5)
O15	0.0446 (8)	0.0368 (7)	0.0233 (7)	0.0273 (6)	0.0064 (6)	0.0031 (5)
O16	0.0266 (6)	0.0349 (7)	0.0295 (7)	0.0214 (6)	0.0088 (5)	0.0031 (5)
C11	0.0316 (9)	0.0275 (9)	0.0219 (8)	0.0184 (8)	0.0091 (7)	0.0047 (7)
C12	0.0228 (8)	0.0239 (8)	0.0230 (8)	0.0148 (7)	0.0077 (7)	0.0034 (6)
C13	0.0227 (8)	0.0203 (8)	0.0251 (8)	0.0137 (7)	0.0079 (7)	0.0043 (6)
C14	0.0241 (8)	0.0198 (8)	0.0256 (9)	0.0125 (7)	0.0127 (7)	0.0073 (6)

Geometric parameters (Å, º)

O27—H27	0.8200	C18—H18A	0.9700
O27—C25	1.289 (2)	C18—H18B	0.9700
O28—C25	1.209 (2)	O21—H21	0.8200
N21—H21A	0.8900	O21—C21	1.2943 (19)
N21—H21B	0.8900	O22—C21	1.216 (2)
N21—H21C	0.8900	O23—H23	0.8200
N21—C28	1.475 (2)	O23—C22	1.4151 (18)
C25—C26	1.500 (2)	O24—H24	0.8200
C26—H26A	0.9700	O24—C23	1.4149 (19)
C26—H26B	0.9700	O25—C24	1.240 (2)
C26—C27	1.527 (2)	O26—C24	1.265 (2)
C27—H27A	0.9700	C21—C22	1.519 (2)
C27—H27B	0.9700	C22—H22	0.9800
C27—C28	1.506 (2)	C22—C23	1.539 (2)
C28—H28A	0.9700	C23—H23A	0.9800
C28—H28B	0.9700	C23—C24	1.531 (2)
O17—H17	0.8200	O11—H11	0.8200
O17—C15	1.277 (2)	O11—C11	1.317 (2)
O18—C15	1.211 (2)	O12—C11	1.204 (2)
N11—H11A	0.8900	O13—H13	0.8200
N11—H11B	0.8900	O13—C12	1.4130 (19)
N11—H11C	0.8900	O14—H14	0.8200
N11—C18	1.483 (2)	O14—C13	1.4171 (19)
C15—C16	1.499 (2)	O15—C14	1.223 (2)
C16—H16A	0.9700	O16—C14	1.278 (2)
C16—H16B	0.9700	C11—C12	1.519 (2)
C16—C17	1.513 (3)	C12—H12	0.9800
C17—H17A	0.9700	C12—C13	1.534 (2)
C17—H17B	0.9700	C13—H13A	0.9800
C17—C18	1.507 (2)	C13—C14	1.527 (2)
C25—O27—H27	109.5	C18—C17—H17B	109.4
H21A—N21—H21B	109.5	N11—C18—C17	111.94 (15)
H21A—N21—H21C	109.5	N11—C18—H18A	109.2
H21B—N21—H21C	109.5	N11—C18—H18B	109.2
C28—N21—H21A	109.5	C17—C18—H18A	109.2
C28—N21—H21B	109.5	C17—C18—H18B	109.2
C28—N21—H21C	109.5	H18A—C18—H18B	107.9
O27—C25—C26	119.29 (16)	C21—O21—H21	109.5
O28—C25—O27	118.87 (17)	C22—O23—H23	109.5
O28—C25—C26	121.83 (18)	C23—O24—H24	109.5
C25—C26—H26A	108.9	O21—C21—C22	112.46 (13)
C25—C26—H26B	108.9	O22—C21—O21	126.04 (15)
C25—C26—C27	113.19 (15)	O22—C21—C22	121.49 (14)
H26A—C26—H26B	107.8	O23—C22—C21	110.75 (13)
C27—C26—H26A	108.9	O23—C22—H22	108.3
C27—C26—H26B	108.9	O23—C22—C23	110.91 (13)
C26—C27—H27A	110.1	C21—C22—H22	108.3
C26—C27—H27B	110.1	C21—C22—C23	110.27 (12)
H27A—C27—H27B	108.4	C23—C22—H22	108.3
C28—C27—C26	108.01 (14)	O24—C23—C22	111.18 (13)
C28—C27—H27A	110.1	O24—C23—H23A	109.0
C28—C27—H27B	110.1	O24—C23—C24	109.88 (13)
N21—C28—C27	113.32 (14)	C22—C23—H23A	109.0
N21—C28—H28A	108.9	C24—C23—C22	108.69 (12)
N21—C28—H28B	108.9	C24—C23—H23A	109.0
C27—C28—H28A	108.9	O25—C24—O26	126.30 (15)
C27—C28—H28B	108.9	O25—C24—C23	119.82 (15)
H28A—C28—H28B	107.7	O26—C24—C23	113.87 (14)
C15—O17—H17	109.5	C11—O11—H11	109.5
H11A—N11—H11B	109.5	C12—O13—H13	109.5
H11A—N11—H11C	109.5	C13—O14—H14	109.5
H11B—N11—H11C	109.5	O11—C11—C12	110.99 (14)
C18—N11—H11A	109.5	O12—C11—O11	124.74 (15)
C18—N11—H11B	109.5	O12—C11—C12	124.27 (15)
C18—N11—H11C	109.5	O13—C12—C11	108.03 (13)
O17—C15—C16	114.47 (16)	O13—C12—H12	108.9
O18—C15—O17	124.07 (17)	O13—C12—C13	110.25 (13)
O18—C15—C16	121.44 (17)	C11—C12—H12	108.9
C15—C16—H16A	108.7	C11—C12—C13	111.91 (13)
C15—C16—H16B	108.7	C13—C12—H12	108.9
C15—C16—C17	114.38 (15)	O14—C13—C12	110.84 (13)
H16A—C16—H16B	107.6	O14—C13—H13A	108.8
C17—C16—H16A	108.7	O14—C13—C14	111.66 (13)
C17—C16—H16B	108.7	C12—C13—H13A	108.8
C16—C17—H17A	109.4	C14—C13—C12	107.91 (12)
C16—C17—H17B	109.4	C14—C13—H13A	108.8
H17A—C17—H17B	108.0	O15—C14—O16	126.40 (15)
C18—C17—C16	111.31 (15)	O15—C14—C13	119.69 (14)
C18—C17—H17A	109.4	O16—C14—C13	113.87 (14)
O27—C25—C26—C27	75.0 (2)	C21—C22—C23—O24	−57.58 (16)
O28—C25—C26—C27	−105.7 (2)	C21—C22—C23—C24	−178.66 (12)
C25—C26—C27—C28	179.31 (16)	C22—C23—C24—O25	121.65 (16)
C26—C27—C28—N21	−178.20 (15)	C22—C23—C24—O26	−57.62 (17)
O17—C15—C16—C17	−177.19 (18)	O11—C11—C12—O13	179.60 (14)
O18—C15—C16—C17	4.1 (3)	O11—C11—C12—C13	58.04 (19)
C15—C16—C17—C18	−173.17 (18)	O12—C11—C12—O13	−1.4 (2)
C16—C17—C18—N11	179.80 (16)	O12—C11—C12—C13	−122.93 (18)
O21—C21—C22—O23	167.67 (13)	O13—C12—C13—O14	−61.98 (16)
O21—C21—C22—C23	−69.19 (17)	O13—C12—C13—C14	60.57 (16)
O22—C21—C22—O23	−13.6 (2)	O14—C13—C14—O15	8.4 (2)
O22—C21—C22—C23	109.58 (17)	O14—C13—C14—O16	−173.69 (13)
O23—C22—C23—O24	65.47 (16)	C11—C12—C13—O14	58.29 (17)
O23—C22—C23—C24	−55.61 (16)	C11—C12—C13—C14	−179.16 (13)
O24—C23—C24—O25	−0.2 (2)	C12—C13—C14—O15	−113.65 (16)
O24—C23—C24—O26	−179.49 (13)	C12—C13—C14—O16	64.26 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O27—H27···O18	0.82	1.76	2.5805 (19)	179
N21—H21A···O25^i	0.89	2.00	2.828 (2)	154
N21—H21B···O15^ii	0.89	2.11	2.8651 (19)	142
N21—H21C···O12^iii	0.89	2.13	2.966 (2)	155
O17—H17···O26	0.82	1.68	2.4663 (17)	161
N11—H11A···O25^i	0.89	2.01	2.8813 (19)	166
N11—H11B···O22^iv	0.89	2.10	2.9105 (19)	151
N11—H11C···O15^ii	0.89	2.50	3.1013 (19)	126
N11—H11C···O16^iv	0.89	2.12	2.8760 (19)	143
O21—H21···O16	0.82	1.66	2.4740 (16)	172
O23—H23···O13^v	0.82	2.06	2.7519 (17)	142
O24—H24···O14^vi	0.82	1.92	2.7346 (16)	174
O11—H11···O28^vi	0.82	1.82	2.6220 (19)	165
O13—H13···O23^vii	0.82	1.91	2.7190 (15)	171
O14—H14···O24^viii	0.82	2.14	2.7986 (17)	138

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

DL-2-Azaniumylbutanoic acid–DL-2-azaniumylbutanoate DL-tartaric acid–DL-tartrate (DL-AABA_DL-tart_V)

Crystal data

C8H19N2O4^+·C8H11O12^−	Z = 1
Mr = 506.42	F(000) = 268
Triclinic, P1	Dx = 1.577 Mg m^−3
a = 4.9336 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.0324 (7) Å	Cell parameters from 3350 reflections
c = 11.3232 (7) Å	θ = 1.9–28.0°
α = 103.464 (6)°	µ = 0.14 mm^−1
β = 94.310 (5)°	T = 293 K
γ = 99.766 (5)°	Block, colourless
V = 533.29 (6) Å^3	0.35 × 0.06 × 0.05 mm

Data collection

Agilent Xcalibur Ruby Gemini ultra diffractometer	2175 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1874 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 10.3457 pixels mm^-1	θmax = 26.4°, θmin = 1.9°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −12→12
Tmin = 0.976, Tmax = 1.000	l = −14→14
6684 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.086	w = 1/[σ^2(Fo^2) + (0.0403P)^2 + 0.1383P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
2175 reflections	Δρmax = 0.25 e Å^−3
191 parameters	Δρmin = −0.18 e Å^−3
23 restraints

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O4	0.75632 (19)	0.32598 (10)	1.01072 (9)	0.0255 (2)
H4	0.897682	0.338873	0.977863	0.031*
O8	1.3362 (2)	0.40774 (11)	0.42712 (9)	0.0280 (2)
O3	0.2374 (2)	0.37769 (11)	0.90602 (10)	0.0297 (3)
H3	0.315593	0.458190	0.911471	0.036*
O5	0.4124 (2)	0.17297 (12)	1.11607 (9)	0.0334 (3)
O2	0.6681 (2)	0.48190 (11)	0.79870 (10)	0.0346 (3)
O7	1.0746 (2)	0.37688 (12)	0.57402 (9)	0.0336 (3)
O6	0.1444 (2)	0.06657 (11)	0.94098 (9)	0.0338 (3)
O1	0.6739 (2)	0.26841 (11)	0.68302 (10)	0.0356 (3)
H1	0.789165	0.311031	0.649796	0.043*
N1	0.9600 (3)	0.28541 (15)	0.24398 (12)	0.0282 (4)	0.929 (2)
H1A	0.807242	0.258948	0.190655	0.042*	0.929 (2)
H1B	1.082913	0.232909	0.218571	0.042*	0.929 (2)
H1C	1.031632	0.374641	0.249848	0.042*	0.929 (2)
C5	1.1146 (3)	0.35785 (14)	0.46582 (12)	0.0212 (3)
C3	0.5533 (3)	0.22179 (14)	0.92920 (12)	0.0202 (3)
H3A	0.645756	0.152254	0.881010	0.024*
C2	0.3900 (3)	0.28414 (14)	0.84129 (12)	0.0210 (3)
H2	0.260983	0.208003	0.783101	0.025*
C4	0.3585 (3)	0.15024 (14)	1.00450 (12)	0.0213 (3)
C1	0.5908 (3)	0.35722 (15)	0.77114 (12)	0.0229 (3)
C6	0.8900 (3)	0.26824 (14)	0.36602 (12)	0.0222 (3)
H6A	0.715811	0.300498	0.380465	0.027*
C7	0.8473 (3)	0.11414 (16)	0.36772 (15)	0.0268 (4)	0.929 (2)
H7A	0.762672	0.102602	0.440209	0.032*	0.929 (2)
H7B	0.719585	0.059729	0.296961	0.032*	0.929 (2)
C8	1.1142 (5)	0.0565 (2)	0.3669 (2)	0.0375 (5)	0.929 (2)
H8A	1.197986	0.065941	0.294702	0.056*	0.929 (2)
H8B	1.072898	−0.040321	0.367434	0.056*	0.929 (2)
H8C	1.239846	0.107750	0.438085	0.056*	0.929 (2)
N1A	0.836 (3)	0.3589 (18)	0.2746 (14)	0.0219 (19)	0.071 (2)
H1AA	0.698469	0.311535	0.216960	0.033*	0.071 (2)
H1AB	0.988911	0.379034	0.239957	0.033*	0.071 (2)
H1AC	0.790358	0.437759	0.314762	0.033*	0.071 (2)
C8A	1.006 (6)	0.066 (3)	0.376 (2)	0.025 (2)	0.071 (2)
H8AA	1.113371	0.121108	0.450788	0.038*	0.071 (2)
H8AB	1.100309	−0.005838	0.338088	0.038*	0.071 (2)
H8AC	0.827912	0.024295	0.392840	0.038*	0.071 (2)
C7A	0.975 (4)	0.141 (2)	0.3067 (19)	0.0248 (12)	0.071 (2)
H7AA	0.836722	0.089739	0.238668	0.030*	0.071 (2)
H7AB	1.148022	0.164339	0.274037	0.030*	0.071 (2)
H8	1.500000	0.500000	0.500000	0.087 (11)*
H6	0.000000	0.000000	1.000000	0.128 (16)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0172 (5)	0.0317 (6)	0.0247 (5)	−0.0050 (4)	0.0030 (4)	0.0084 (4)
O8	0.0209 (5)	0.0341 (6)	0.0230 (5)	−0.0046 (4)	0.0042 (4)	0.0023 (4)
O3	0.0265 (5)	0.0270 (5)	0.0400 (6)	0.0069 (4)	0.0147 (5)	0.0123 (5)
O5	0.0285 (6)	0.0457 (7)	0.0241 (5)	−0.0075 (5)	0.0017 (4)	0.0159 (5)
O2	0.0443 (7)	0.0258 (6)	0.0340 (6)	−0.0013 (5)	0.0141 (5)	0.0111 (5)
O7	0.0312 (6)	0.0435 (6)	0.0219 (5)	−0.0018 (5)	0.0079 (4)	0.0048 (5)
O6	0.0300 (6)	0.0382 (6)	0.0274 (6)	−0.0144 (5)	−0.0002 (4)	0.0129 (5)
O1	0.0430 (7)	0.0322 (6)	0.0336 (6)	0.0039 (5)	0.0212 (5)	0.0090 (5)
N1	0.0278 (7)	0.0307 (8)	0.0237 (7)	−0.0032 (6)	−0.0036 (5)	0.0106 (6)
C5	0.0204 (6)	0.0211 (7)	0.0221 (7)	0.0041 (5)	0.0036 (5)	0.0051 (5)
C3	0.0178 (6)	0.0201 (7)	0.0218 (7)	−0.0003 (5)	0.0043 (5)	0.0059 (5)
C2	0.0200 (7)	0.0213 (7)	0.0210 (7)	0.0000 (5)	0.0042 (5)	0.0062 (5)
C4	0.0212 (7)	0.0206 (7)	0.0229 (7)	0.0010 (5)	0.0033 (5)	0.0086 (5)
C1	0.0233 (7)	0.0273 (7)	0.0195 (7)	0.0029 (6)	0.0031 (5)	0.0098 (6)
C6	0.0168 (6)	0.0263 (7)	0.0234 (7)	0.0020 (5)	0.0033 (5)	0.0073 (6)
C7	0.0267 (8)	0.0241 (8)	0.0279 (8)	−0.0016 (7)	0.0023 (7)	0.0078 (6)
C8	0.0407 (12)	0.0313 (10)	0.0431 (11)	0.0151 (10)	0.0014 (10)	0.0100 (8)
N1A	0.018 (4)	0.027 (3)	0.019 (4)	0.001 (3)	0.003 (3)	0.004 (3)
C8A	0.018 (4)	0.027 (4)	0.027 (4)	0.003 (4)	0.001 (4)	0.002 (4)
C7A	0.019 (2)	0.028 (2)	0.026 (2)	0.0018 (19)	0.003 (2)	0.0044 (19)

Geometric parameters (Å, º)

O4—H4	0.8200	C2—H2	0.9800
O4—C3	1.4157 (16)	C2—C1	1.5142 (18)
O8—C5	1.2750 (16)	C6—H6A	0.9800
O8—H8	1.2170 (9)	C6—C7	1.529 (2)
O3—H3	0.8200	C6—N1A	1.565 (16)
O3—C2	1.4098 (16)	C6—C7A	1.44 (2)
O5—C4	1.2301 (16)	C7—H7A	0.9700
O2—C1	1.2025 (17)	C7—H7B	0.9700
O7—C5	1.2315 (16)	C7—C8	1.525 (3)
O6—C4	1.2813 (16)	C8—H8A	0.9600
O6—H6	1.2322 (9)	C8—H8B	0.9600
O1—H1	0.8200	C8—H8C	0.9600
O1—C1	1.3148 (17)	N1A—H1AA	0.8900
N1—H1A	0.8900	N1A—H1AB	0.8900
N1—H1B	0.8900	N1A—H1AC	0.8900
N1—H1C	0.8900	C8A—H8AA	0.9600
N1—C6	1.4902 (18)	C8A—H8AB	0.9600
C5—C6	1.5214 (18)	C8A—H8AC	0.9600
C3—H3A	0.9800	C8A—C7A	1.22 (4)
C3—C2	1.5400 (18)	C7A—H7AA	0.9700
C3—C4	1.5297 (17)	C7A—H7AB	0.9700
C3—O4—H4	109.5	C5—C6—C7	111.67 (11)
C5—O8—H8	116.90 (10)	C5—C6—N1A	106.9 (6)
C2—O3—H3	109.5	C7—C6—H6A	108.2
C4—O6—H6	114.10 (10)	C7A—C6—C5	110.5 (8)
C1—O1—H1	109.5	C7A—C6—N1A	112.0 (10)
H1A—N1—H1B	109.5	C6—C7—H7A	108.8
H1A—N1—H1C	109.5	C6—C7—H7B	108.8
H1B—N1—H1C	109.5	H7A—C7—H7B	107.7
C6—N1—H1A	109.5	C8—C7—C6	113.72 (14)
C6—N1—H1B	109.5	C8—C7—H7A	108.8
C6—N1—H1C	109.5	C8—C7—H7B	108.8
O8—C5—C6	114.66 (11)	C7—C8—H8A	109.5
O7—C5—O8	125.25 (13)	C7—C8—H8B	109.5
O7—C5—C6	120.10 (12)	C7—C8—H8C	109.5
O4—C3—H3A	108.8	H8A—C8—H8B	109.5
O4—C3—C2	111.44 (11)	H8A—C8—H8C	109.5
O4—C3—C4	108.41 (10)	H8B—C8—H8C	109.5
C2—C3—H3A	108.8	C6—N1A—H1AA	109.5
C4—C3—H3A	108.8	C6—N1A—H1AB	109.5
C4—C3—C2	110.64 (11)	C6—N1A—H1AC	109.5
O3—C2—C3	110.81 (11)	H1AA—N1A—H1AB	109.5
O3—C2—H2	108.8	H1AA—N1A—H1AC	109.5
O3—C2—C1	110.71 (11)	H1AB—N1A—H1AC	109.5
C3—C2—H2	108.8	H8AA—C8A—H8AB	109.5
C1—C2—C3	108.97 (11)	H8AA—C8A—H8AC	109.5
C1—C2—H2	108.8	H8AB—C8A—H8AC	109.5
O5—C4—O6	124.93 (12)	C7A—C8A—H8AA	109.5
O5—C4—C3	120.95 (12)	C7A—C8A—H8AB	109.5
O6—C4—C3	114.12 (11)	C7A—C8A—H8AC	109.5
O2—C1—O1	125.78 (13)	C6—C7A—H7AA	109.0
O2—C1—C2	122.08 (13)	C6—C7A—H7AB	109.0
O1—C1—C2	112.08 (12)	C8A—C7A—C6	113 (2)
N1—C6—C5	110.10 (11)	C8A—C7A—H7AA	109.0
N1—C6—H6A	108.2	C8A—C7A—H7AB	109.0
N1—C6—C7	110.26 (12)	H7AA—C7A—H7AB	107.8
C5—C6—H6A	108.2
O4—C3—C2—O3	−64.28 (13)	O7—C5—C6—N1A	125.5 (7)
O4—C3—C2—C1	57.77 (14)	O7—C5—C6—C7A	−112.4 (9)
O4—C3—C4—O5	−9.52 (18)	N1—C6—C7—C8	71.12 (17)
O4—C3—C4—O6	171.22 (12)	C5—C6—C7—C8	−51.63 (18)
O8—C5—C6—N1	−12.38 (17)	C5—C6—C7A—C8A	64 (2)
O8—C5—C6—C7	110.46 (14)	C3—C2—C1—O2	−100.37 (15)
O8—C5—C6—N1A	−54.6 (7)	C3—C2—C1—O1	77.04 (14)
O8—C5—C6—C7A	67.5 (9)	C2—C3—C4—O5	−132.00 (14)
O3—C2—C1—O2	21.74 (18)	C2—C3—C4—O6	48.74 (16)
O3—C2—C1—O1	−160.85 (12)	C4—C3—C2—O3	56.41 (14)
O7—C5—C6—N1	167.80 (13)	C4—C3—C2—C1	178.47 (11)
O7—C5—C6—C7	−69.36 (17)	N1A—C6—C7A—C8A	−176.9 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3^i	0.82	1.94	2.7567 (13)	177
O3—H3···O4^ii	0.82	2.24	2.8961 (14)	138
O1—H1···O7	0.82	1.81	2.6228 (14)	169
N1—H1A···O4^iii	0.89	2.30	2.8969 (16)	125
N1—H1A···O5^iii	0.89	2.02	2.8785 (16)	161
N1—H1B···O5^iv	0.89	2.15	2.9887 (19)	156
N1—H1C···O2^v	0.89	2.08	2.8733 (16)	148
N1A—H1AA···O5^iii	0.89	1.89	2.761 (16)	165
N1A—H1AB···O2^v	0.89	2.14	2.970 (16)	154
N1A—H1AC···O7^v	0.89	1.96	2.745 (17)	146
C7A—H7AA···O6^vi	0.97	2.28	3.03 (2)	133
O6—H6···O6^vii	1.23	1.23	2.4644 (19)	180
O8—H8···O8^viii	1.22	1.22	2.4341 (19)	180

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+2; (iii) x, y, z−1; (iv) x+1, y, z−1; (v) −x+2, −y+1, −z+1; (vi) −x+1, −y, −z+1; (vii) −x, −y, −z+2; (viii) −x+3, −y+1, −z+1.