Low-temperature phase transition in glycine–glutaric acid co-crystals studied by single-crystal X-ray diffraction, Raman spectroscopy and differential scanning calorimetry

Zakharov, B.A.; Losev, E.A.; Kolesov, B.A.; Drebushchak, V.A.; Boldyreva, E.V.

doi:10.1107/S0108768112015972

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Low-temperature phase transition in glycine-glutaric acid co-crystals studied by single-crystal X-ray diffraction, Raman spectroscopy and differential scanning calorimetry

B. A. Zakharov, E. A. Losev, B. A. Kolesov, V. A. Drebushchak and E. V. Boldyreva

The occurrence of a first-order reversible phase transition in glycine-glutaric acid co-crystals at 220-230 K has been confirmed by three different techniques - single-crystal X-ray diffraction, polarized Raman spectroscopy and differential scanning calorimetry. The most interesting feature of this phase transition is that every second glutaric acid molecule changes its conformation, and this fact results in the space-group symmetry change from P2₁/c to $P\bar 1$ . The topology of the hydrogen-bonded motifs remains almost the same and hydrogen bonds do not switch to other atoms, although the hydrogen bond lengths do change and some of the bonds become inequivalent.

Keywords: phase transition; amino acid co-crystals; hydrogen bonds; single-crystal to single-crystal transformation; conformational polymorphism.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768112015972/gp5050sup1.cif Contains datablocks 300, 275, 250, 225, 200, 175, 150, 125, 100
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768112015972/gp5050300sup2.hkl Contains datablock 300
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768112015972/gp5050275sup3.hkl Contains datablock 275
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768112015972/gp5050250sup4.hkl Contains datablock 250
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768112015972/gp5050225sup5.hkl Contains datablock 225
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768112015972/gp5050100sup6.hkl Contains datablock 100
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768112015972/gp5050125sup7.hkl Contains datablock 125
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768112015972/gp5050150sup8.hkl Contains datablock 150
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768112015972/gp5050175sup9.hkl Contains datablock 175
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768112015972/gp5050200sup10.hkl Contains datablock 200
	Portable Document Format (PDF) file https://doi.org/10.1107/S0108768112015972/gp5050sup11.pdf Procedure of indexing diffraction patterns from domains in glycine and photographs of co-crystal

CCDC references: 889409; 889410; 889411; 889412; 889413; 889414; 889415; 889416; 889417

Computing details top

For all compounds, data collection: STOE X-AREA (Stoe & Cie, 2006); cell refinement: STOE X-AREA (Stoe & Cie, 2006); data reduction: STOE X-RED (Stoe & Cie, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and X-STEP32 (Stoe & Cie, 2000); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: Mercury (Macrae et al., 2006), PLATON (Spek, 2009), enCIFer (Allen et al., 2004).

Figures top

(300) Propane-1,3-dicarboxylic acid – Aminoethanoic acid (1/1) top

Crystal data top

C₅H₈O₄·C₂H₅NO₂	F(000) = 440
M_r = 207.18	D_x = 1.434 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3307 reflections
a = 4.9110 (7) Å	θ = 2.0–29.2°
b = 20.922 (3) Å	µ = 0.13 mm⁻¹
c = 10.2744 (15) Å	T = 300 K
β = 114.586 (10)°	Prism, colourless
V = 959.9 (2) Å³	0.32 × 0.17 × 0.10 mm
Z = 4

Data collection top

STOE IPDS 2 diffractometer	1421 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.046
Detector resolution: 6.67 pixels mm^-1	θ_max = 29.2°, θ_min = 2.0°
rotation method scans	h = −5→6
6828 measured reflections	k = −28→24
2578 independent reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: difference Fourier map
wR(F²) = 0.096	H-atom parameters constrained
S = 0.89	w = 1/[σ²(F_o²) + (0.0419P)²] where P = (F_o² + 2F_c²)/3
2578 reflections	(Δ/σ)_max < 0.001
130 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₅H₈O₄·C₂H₅NO₂	V = 959.9 (2) Å³
M_r = 207.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.9110 (7) Å	µ = 0.13 mm⁻¹
b = 20.922 (3) Å	T = 300 K
c = 10.2744 (15) Å	0.32 × 0.17 × 0.10 mm
β = 114.586 (10)°

Data collection top

STOE IPDS 2 diffractometer	1421 reflections with I > 2σ(I)
6828 measured reflections	R_int = 0.046
2578 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 0.89	Δρ_max = 0.19 e Å⁻³
2578 reflections	Δρ_min = −0.17 e Å⁻³
130 parameters

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.1303 (3)	0.44553 (6)	0.33353 (12)	0.0431 (3)
O5	0.6180 (3)	0.64113 (6)	0.22044 (13)	0.0492 (4)
O3	0.2017 (3)	0.91549 (6)	−0.03314 (12)	0.0412 (3)
N1	0.5566 (4)	0.52554 (7)	0.33624 (14)	0.0360 (4)
H1A	0.6599	0.5565	0.3179	0.054*
H1B	0.6819	0.5000	0.4039	0.054*
H1C	0.4268	0.5426	0.3661	0.054*
C2	0.3932 (4)	0.48823 (8)	0.20491 (17)	0.0334 (4)
H2A	0.5357	0.4649	0.1802	0.040*
H2B	0.2843	0.5172	0.1268	0.040*
O6	0.8167 (4)	0.59463 (6)	0.09106 (14)	0.0501 (4)
H6	0.8418	0.6018	0.0184	0.075*
O2	0.0510 (3)	0.40246 (7)	0.12345 (14)	0.0543 (4)
C1	0.1753 (4)	0.44149 (8)	0.22259 (17)	0.0332 (4)
C7	0.6740 (4)	0.64281 (8)	0.11621 (17)	0.0347 (4)
O4	0.1063 (4)	0.84677 (6)	0.10598 (16)	0.0565 (4)
H4	0.0356	0.8788	0.1260	0.085*
C5	0.4645 (5)	0.75376 (9)	0.06721 (18)	0.0423 (5)
H5A	0.3195	0.7383	0.1012	0.051*
H5B	0.6295	0.7725	0.1481	0.051*
C6	0.5810 (5)	0.69752 (8)	0.01277 (18)	0.0379 (4)
H6B	0.4261	0.6831	−0.0774	0.045*
H6A	0.7512	0.7112	−0.0050	0.045*
C3	0.2064 (4)	0.86107 (8)	0.01003 (17)	0.0345 (4)
C4	0.3204 (5)	0.80483 (9)	−0.04245 (19)	0.0443 (5)
H4A	0.4651	0.8199	−0.0771	0.053*
H4B	0.1546	0.7861	−0.1230	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0537 (9)	0.0417 (7)	0.0454 (7)	−0.0153 (7)	0.0319 (6)	−0.0063 (6)
O5	0.0761 (11)	0.0384 (7)	0.0480 (7)	0.0049 (7)	0.0405 (7)	0.0067 (6)
O3	0.0536 (9)	0.0293 (6)	0.0473 (7)	0.0004 (6)	0.0275 (6)	0.0027 (5)
N1	0.0422 (10)	0.0321 (8)	0.0396 (7)	−0.0084 (7)	0.0228 (7)	0.0000 (6)
C2	0.0348 (11)	0.0350 (9)	0.0344 (8)	−0.0021 (8)	0.0186 (8)	−0.0002 (7)
O6	0.0726 (11)	0.0360 (7)	0.0510 (8)	0.0163 (7)	0.0349 (8)	0.0061 (6)
O2	0.0612 (10)	0.0556 (9)	0.0575 (8)	−0.0243 (8)	0.0358 (7)	−0.0237 (7)
C1	0.0331 (11)	0.0306 (9)	0.0389 (9)	0.0014 (8)	0.0180 (8)	−0.0015 (7)
C7	0.0408 (12)	0.0277 (9)	0.0377 (8)	−0.0027 (8)	0.0184 (8)	−0.0020 (7)
O4	0.0853 (12)	0.0378 (8)	0.0758 (9)	0.0195 (8)	0.0627 (9)	0.0160 (7)
C5	0.0587 (14)	0.0335 (10)	0.0419 (9)	0.0103 (9)	0.0280 (9)	0.0057 (7)
C6	0.0483 (13)	0.0325 (9)	0.0398 (9)	0.0048 (9)	0.0252 (9)	0.0037 (7)
C3	0.0374 (11)	0.0328 (9)	0.0367 (9)	0.0041 (8)	0.0189 (8)	0.0041 (7)
C4	0.0581 (14)	0.0389 (11)	0.0461 (10)	0.0129 (10)	0.0318 (10)	0.0087 (8)

Geometric parameters (Å, º) top

O1—C1	1.2508 (19)	C7—C6	1.498 (2)
O5—C7	1.212 (2)	O4—C3	1.306 (2)
O3—C3	1.219 (2)	O4—H4	0.8200
N1—C2	1.474 (2)	C5—C4	1.500 (2)
N1—H1A	0.8900	C5—C6	1.514 (2)
N1—H1B	0.8900	C5—H5A	0.9700
N1—H1C	0.8900	C5—H5B	0.9700
C2—C1	1.515 (2)	C6—H6B	0.9700
C2—H2A	0.9700	C6—H6A	0.9700
C2—H2B	0.9700	C3—C4	1.497 (2)
O6—C7	1.313 (2)	C4—H4A	0.9700
O6—H6	0.8200	C4—H4B	0.9700
O2—C1	1.249 (2)

C2—N1—H1A	109.5	C4—C5—H5A	108.7
C2—N1—H1B	109.5	C6—C5—H5A	108.7
H1A—N1—H1B	109.5	C4—C5—H5B	108.7
C2—N1—H1C	109.5	C6—C5—H5B	108.7
H1A—N1—H1C	109.5	H5A—C5—H5B	107.6
H1B—N1—H1C	109.5	C7—C6—C5	112.48 (13)
N1—C2—C1	112.00 (13)	C7—C6—H6B	109.1
N1—C2—H2A	109.2	C5—C6—H6B	109.1
C1—C2—H2A	109.2	C7—C6—H6A	109.1
N1—C2—H2B	109.2	C5—C6—H6A	109.1
C1—C2—H2B	109.2	H6B—C6—H6A	107.8
H2A—C2—H2B	107.9	O3—C3—O4	122.19 (16)
C7—O6—H6	109.5	O3—C3—C4	123.82 (15)
O2—C1—O1	125.15 (17)	O4—C3—C4	113.98 (15)
O2—C1—C2	117.00 (15)	C3—C4—C5	114.82 (14)
O1—C1—C2	117.83 (15)	C3—C4—H4A	108.6
O5—C7—O6	119.17 (15)	C5—C4—H4A	108.6
O5—C7—C6	122.33 (16)	C3—C4—H4B	108.6
O6—C7—C6	118.49 (14)	C5—C4—H4B	108.6
C3—O4—H4	109.5	H4A—C4—H4B	107.5
C4—C5—C6	114.14 (14)

N1—C2—C1—O2	−171.95 (16)	C4—C5—C6—C7	−170.01 (18)
N1—C2—C1—O1	9.1 (2)	O3—C3—C4—C5	147.7 (2)
O5—C7—C6—C5	10.4 (3)	O4—C3—C4—C5	−33.3 (3)
O6—C7—C6—C5	−170.82 (17)	C6—C5—C4—C3	−179.48 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O3ⁱ	0.89	2.14	2.9671 (19)	154
N1—H1C···O3ⁱⁱ	0.89	2.00	2.8824 (19)	169
N1—H1A···O5	0.89	2.00	2.7665 (18)	143
O4—H4···O1ⁱⁱⁱ	0.82	1.75	2.5706 (18)	178
O6—H6···O2^iv	0.82	1.75	2.5444 (18)	164

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

(275) Propane-1,3-dicarboxylic acid – Aminoethanoic acid (1/1) top

Crystal data top

C₅H₈O₄·C₂H₅NO₂	F(000) = 440
M_r = 207.18	D_x = 1.438 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3205 reflections
a = 4.9022 (7) Å	θ = 2.0–29.2°
b = 20.901 (3) Å	µ = 0.13 mm⁻¹
c = 10.2730 (15) Å	T = 275 K
β = 114.60 (1)°	Prism, colourless
V = 957.0 (2) Å³	0.32 × 0.17 × 0.10 mm
Z = 4

Data collection top

STOE IPDS 2 diffractometer	1461 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.047
Detector resolution: 6.67 pixels mm^-1	θ_max = 29.2°, θ_min = 2.0°
rotation method scans	h = −5→6
6792 measured reflections	k = −28→24
2570 independent reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: difference Fourier map
wR(F²) = 0.085	H-atom parameters constrained
S = 0.87	w = 1/[σ²(F_o²) + (0.0364P)²] where P = (F_o² + 2F_c²)/3
2570 reflections	(Δ/σ)_max = 0.001
130 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₅H₈O₄·C₂H₅NO₂	V = 957.0 (2) Å³
M_r = 207.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.9022 (7) Å	µ = 0.13 mm⁻¹
b = 20.901 (3) Å	T = 275 K
c = 10.2730 (15) Å	0.32 × 0.17 × 0.10 mm
β = 114.60 (1)°

Data collection top

STOE IPDS 2 diffractometer	1461 reflections with I > 2σ(I)
6792 measured reflections	R_int = 0.047
2570 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 0.87	Δρ_max = 0.16 e Å⁻³
2570 reflections	Δρ_min = −0.18 e Å⁻³
130 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.1302 (3)	0.44534 (6)	0.33384 (11)	0.0391 (3)
O5	0.6205 (3)	0.64085 (6)	0.22111 (12)	0.0434 (3)
O3	0.2021 (3)	0.91559 (5)	−0.03340 (11)	0.0368 (3)
N1	0.5575 (3)	0.52520 (6)	0.33659 (13)	0.0325 (3)
H1A	0.6613	0.5562	0.3184	0.049*
H1B	0.6827	0.4996	0.4043	0.049*
H1C	0.4274	0.5424	0.3664	0.049*
C2	0.3937 (4)	0.48788 (8)	0.20508 (15)	0.0302 (4)
H2A	0.5364	0.4643	0.1807	0.036*
H2B	0.2857	0.5170	0.1269	0.036*
O6	0.8202 (3)	0.59420 (6)	0.09161 (12)	0.0452 (3)
H6	0.8488	0.6018	0.0200	0.068*
O2	0.0470 (3)	0.40245 (6)	0.12262 (13)	0.0489 (4)
C1	0.1736 (4)	0.44130 (8)	0.22219 (16)	0.0304 (4)
C7	0.6768 (4)	0.64243 (8)	0.11682 (16)	0.0310 (4)
O4	0.1064 (4)	0.84659 (6)	0.10554 (15)	0.0518 (4)
H4	0.0380	0.8788	0.1264	0.078*
C5	0.4674 (4)	0.75361 (8)	0.06781 (16)	0.0377 (4)
H5A	0.3234	0.7382	0.1026	0.045*
H5B	0.6335	0.7725	0.1482	0.045*
C6	0.5829 (4)	0.69733 (7)	0.01302 (17)	0.0341 (4)
H6B	0.4271	0.6830	−0.0770	0.041*
H6A	0.7530	0.7110	−0.0051	0.041*
C3	0.2068 (4)	0.86087 (8)	0.00940 (16)	0.0321 (4)
C4	0.3207 (5)	0.80467 (8)	−0.04307 (17)	0.0398 (5)
H4A	0.4646	0.8197	−0.0783	0.048*
H4B	0.1543	0.7857	−0.1231	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0477 (8)	0.0394 (7)	0.0401 (6)	−0.0147 (6)	0.0281 (6)	−0.0068 (5)
O5	0.0665 (10)	0.0342 (7)	0.0416 (6)	0.0049 (7)	0.0346 (7)	0.0065 (5)
O3	0.0474 (8)	0.0267 (6)	0.0414 (6)	0.0001 (6)	0.0234 (6)	0.0021 (5)
N1	0.0377 (9)	0.0291 (7)	0.0369 (7)	−0.0079 (7)	0.0218 (6)	0.0001 (6)
C2	0.0314 (10)	0.0312 (8)	0.0310 (8)	−0.0021 (8)	0.0158 (7)	−0.0006 (6)
O6	0.0660 (10)	0.0323 (7)	0.0462 (7)	0.0155 (7)	0.0321 (7)	0.0058 (5)
O2	0.0540 (9)	0.0498 (8)	0.0525 (7)	−0.0223 (7)	0.0318 (7)	−0.0231 (6)
C1	0.0294 (10)	0.0269 (8)	0.0379 (8)	0.0016 (8)	0.0168 (7)	−0.0005 (7)
C7	0.0349 (10)	0.0251 (8)	0.0340 (8)	−0.0020 (8)	0.0153 (7)	−0.0016 (6)
O4	0.0787 (11)	0.0346 (7)	0.0694 (8)	0.0180 (7)	0.0579 (8)	0.0149 (6)
C5	0.0517 (12)	0.0303 (9)	0.0382 (8)	0.0092 (9)	0.0256 (8)	0.0048 (7)
C6	0.0438 (12)	0.0285 (8)	0.0368 (8)	0.0053 (8)	0.0234 (8)	0.0035 (7)
C3	0.0347 (11)	0.0317 (9)	0.0326 (8)	0.0033 (8)	0.0166 (8)	0.0037 (7)
C4	0.0525 (13)	0.0345 (10)	0.0410 (9)	0.0109 (9)	0.0279 (9)	0.0073 (7)

Geometric parameters (Å, º) top

O1—C1	1.2534 (18)	C7—C6	1.502 (2)
O5—C7	1.2132 (18)	O4—C3	1.3082 (19)
O3—C3	1.2221 (19)	O4—H4	0.8200
N1—C2	1.4749 (19)	C5—C4	1.507 (2)
N1—H1A	0.8900	C5—C6	1.512 (2)
N1—H1B	0.8900	C5—H5A	0.9700
N1—H1C	0.8900	C5—H5B	0.9700
C2—C1	1.517 (2)	C6—H6B	0.9700
C2—H2A	0.9700	C6—H6A	0.9700
C2—H2B	0.9700	C3—C4	1.494 (2)
O6—C7	1.3149 (19)	C4—H4A	0.9700
O6—H6	0.8200	C4—H4B	0.9700
O2—C1	1.2499 (19)

C2—N1—H1A	109.5	C4—C5—H5A	108.8
C2—N1—H1B	109.5	C6—C5—H5A	108.8
H1A—N1—H1B	109.5	C4—C5—H5B	108.8
C2—N1—H1C	109.5	C6—C5—H5B	108.8
H1A—N1—H1C	109.5	H5A—C5—H5B	107.7
H1B—N1—H1C	109.5	C7—C6—C5	112.43 (12)
N1—C2—C1	112.07 (12)	C7—C6—H6B	109.1
N1—C2—H2A	109.2	C5—C6—H6B	109.1
C1—C2—H2A	109.2	C7—C6—H6A	109.1
N1—C2—H2B	109.2	C5—C6—H6A	109.1
C1—C2—H2B	109.2	H6B—C6—H6A	107.9
H2A—C2—H2B	107.9	O3—C3—O4	121.90 (15)
C7—O6—H6	109.5	O3—C3—C4	124.04 (14)
O2—C1—O1	125.25 (16)	O4—C3—C4	114.06 (14)
O2—C1—C2	117.19 (14)	C3—C4—C5	114.62 (13)
O1—C1—C2	117.56 (14)	C3—C4—H4A	108.6
O5—C7—O6	119.35 (14)	C5—C4—H4A	108.6
O5—C7—C6	122.17 (15)	C3—C4—H4B	108.6
O6—C7—C6	118.47 (13)	C5—C4—H4B	108.6
C3—O4—H4	109.5	H4A—C4—H4B	107.6
C4—C5—C6	113.85 (13)

N1—C2—C1—O2	−172.37 (15)	C4—C5—C6—C7	−169.69 (17)
N1—C2—C1—O1	8.5 (2)	O3—C3—C4—C5	147.16 (18)
O5—C7—C6—C5	10.6 (3)	O4—C3—C4—C5	−33.7 (2)
O6—C7—C6—C5	−170.55 (16)	C6—C5—C4—C3	−179.64 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O3ⁱ	0.89	2.13	2.9564 (18)	154
N1—H1C···O3ⁱⁱ	0.89	2.00	2.8789 (18)	169
N1—H1A···O5	0.89	2.00	2.7658 (17)	143
O4—H4···O1ⁱⁱⁱ	0.82	1.75	2.5680 (17)	176
O6—H6···O2^iv	0.82	1.74	2.5425 (17)	165

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

(250) Propane-1,3-dicarboxylic acid – Aminoethanoic acid (1/1) top

Crystal data top

C₅H₈O₄·C₂H₅NO₂	F(000) = 440
M_r = 207.18	D_x = 1.442 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3499 reflections
a = 4.8960 (6) Å	θ = 2.0–29.5°
b = 20.878 (2) Å	µ = 0.13 mm⁻¹
c = 10.2701 (13) Å	T = 250 K
β = 114.634 (9)°	Prism, colourless
V = 954.3 (2) Å³	0.32 × 0.17 × 0.10 mm
Z = 4

Data collection top

STOE IPDS 2 diffractometer	1535 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.045
Detector resolution: 6.67 pixels mm^-1	θ_max = 29.2°, θ_min = 2.0°
rotation method scans	h = −5→6
6775 measured reflections	k = −28→24
2562 independent reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: difference Fourier map
wR(F²) = 0.086	H-atom parameters constrained
S = 0.88	w = 1/[σ²(F_o²) + (0.0377P)²] where P = (F_o² + 2F_c²)/3
2562 reflections	(Δ/σ)_max < 0.001
130 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₅H₈O₄·C₂H₅NO₂	V = 954.3 (2) Å³
M_r = 207.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.8960 (6) Å	µ = 0.13 mm⁻¹
b = 20.878 (2) Å	T = 250 K
c = 10.2701 (13) Å	0.32 × 0.17 × 0.10 mm
β = 114.634 (9)°

Data collection top

STOE IPDS 2 diffractometer	1535 reflections with I > 2σ(I)
6775 measured reflections	R_int = 0.045
2562 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 0.88	Δρ_max = 0.16 e Å⁻³
2562 reflections	Δρ_min = −0.20 e Å⁻³
130 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.1300 (3)	0.44533 (6)	0.33405 (11)	0.0352 (3)
O5	0.6231 (3)	0.64055 (5)	0.22156 (11)	0.0386 (3)
O3	0.2029 (3)	0.91557 (5)	−0.03367 (11)	0.0332 (3)
N1	0.5587 (3)	0.52504 (6)	0.33685 (13)	0.0294 (3)
H1A	0.6627	0.5566	0.3182	0.044*
H1B	0.6866	0.4992	0.4053	0.044*
H1C	0.4270	0.5422	0.3673	0.044*
C2	0.3943 (4)	0.48752 (7)	0.20504 (15)	0.0277 (3)
H2A	0.5386	0.4635	0.1808	0.033*
H2B	0.2860	0.5169	0.1258	0.033*
O6	0.8236 (3)	0.59387 (6)	0.09217 (12)	0.0411 (3)
H6	0.8544	0.6018	0.0202	0.062*
O2	0.0439 (3)	0.40249 (6)	0.12210 (13)	0.0446 (3)
C1	0.1725 (4)	0.44122 (8)	0.22194 (15)	0.0275 (3)
C7	0.6793 (4)	0.64212 (7)	0.11717 (15)	0.0280 (3)
O4	0.1064 (3)	0.84645 (6)	0.10527 (14)	0.0464 (4)
H4	0.0338	0.8789	0.1252	0.070*
C5	0.4699 (4)	0.75347 (8)	0.06795 (16)	0.0331 (4)
H5A	0.3249	0.7379	0.1036	0.040*
H5B	0.6381	0.7728	0.1488	0.040*
C6	0.5856 (4)	0.69709 (7)	0.01315 (16)	0.0304 (4)
H6B	0.4280	0.6826	−0.0779	0.036*
H6A	0.7579	0.7109	−0.0050	0.036*
C3	0.2068 (4)	0.86084 (8)	0.00894 (15)	0.0284 (4)
C4	0.3212 (4)	0.80446 (8)	−0.04366 (17)	0.0348 (4)
H4A	0.4662	0.8197	−0.0797	0.042*
H4B	0.1528	0.7851	−0.1243	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0427 (8)	0.0349 (6)	0.0366 (6)	−0.0127 (6)	0.0251 (5)	−0.0051 (5)
O5	0.0582 (9)	0.0310 (6)	0.0371 (6)	0.0045 (6)	0.0304 (6)	0.0058 (5)
O3	0.0418 (8)	0.0242 (6)	0.0384 (6)	−0.0003 (6)	0.0216 (5)	0.0020 (5)
N1	0.0346 (8)	0.0264 (7)	0.0326 (6)	−0.0066 (6)	0.0193 (6)	0.0002 (5)
C2	0.0288 (9)	0.0284 (8)	0.0288 (7)	−0.0002 (7)	0.0151 (7)	0.0000 (6)
O6	0.0596 (9)	0.0301 (6)	0.0415 (6)	0.0143 (6)	0.0291 (6)	0.0057 (5)
O2	0.0492 (9)	0.0463 (7)	0.0468 (7)	−0.0206 (7)	0.0285 (6)	−0.0213 (6)
C1	0.0272 (9)	0.0254 (8)	0.0326 (7)	0.0016 (7)	0.0152 (7)	0.0007 (6)
C7	0.0327 (10)	0.0223 (7)	0.0298 (7)	−0.0022 (7)	0.0139 (7)	−0.0016 (6)
O4	0.0712 (10)	0.0300 (7)	0.0632 (8)	0.0166 (7)	0.0529 (7)	0.0134 (6)
C5	0.0459 (11)	0.0253 (8)	0.0336 (8)	0.0076 (8)	0.0219 (7)	0.0044 (6)
C6	0.0391 (11)	0.0256 (8)	0.0321 (8)	0.0036 (7)	0.0205 (7)	0.0029 (6)
C3	0.0301 (10)	0.0276 (8)	0.0300 (7)	0.0020 (7)	0.0150 (7)	0.0032 (6)
C4	0.0460 (12)	0.0296 (9)	0.0352 (8)	0.0106 (8)	0.0234 (8)	0.0069 (6)

Geometric parameters (Å, º) top

O1—C1	1.2553 (17)	C7—C6	1.503 (2)
O5—C7	1.2133 (18)	O4—C3	1.3098 (19)
O3—C3	1.2210 (18)	O4—H4	0.8300
N1—C2	1.4783 (19)	C5—C4	1.510 (2)
N1—H1A	0.9000	C5—C6	1.513 (2)
N1—H1B	0.9000	C5—H5A	0.9800
N1—H1C	0.9000	C5—H5B	0.9800
C2—C1	1.517 (2)	C6—H6B	0.9800
C2—H2A	0.9800	C6—H6A	0.9800
C2—H2B	0.9800	C3—C4	1.498 (2)
O6—C7	1.3157 (19)	C4—H4A	0.9800
O6—H6	0.8300	C4—H4B	0.9800
O2—C1	1.2503 (19)

C2—N1—H1A	109.5	C4—C5—H5A	108.8
C2—N1—H1B	109.5	C6—C5—H5A	108.8
H1A—N1—H1B	109.5	C4—C5—H5B	108.8
C2—N1—H1C	109.5	C6—C5—H5B	108.8
H1A—N1—H1C	109.5	H5A—C5—H5B	107.7
H1B—N1—H1C	109.5	C7—C6—C5	112.35 (12)
N1—C2—C1	112.06 (12)	C7—C6—H6B	109.1
N1—C2—H2A	109.2	C5—C6—H6B	109.1
C1—C2—H2A	109.2	C7—C6—H6A	109.1
N1—C2—H2B	109.2	C5—C6—H6A	109.1
C1—C2—H2B	109.2	H6B—C6—H6A	107.9
H2A—C2—H2B	107.9	O3—C3—O4	122.06 (15)
C7—O6—H6	109.5	O3—C3—C4	123.95 (14)
O2—C1—O1	125.25 (15)	O4—C3—C4	113.99 (13)
O2—C1—C2	117.26 (13)	C3—C4—C5	114.49 (12)
O1—C1—C2	117.48 (13)	C3—C4—H4A	108.6
O5—C7—O6	119.32 (14)	C5—C4—H4A	108.6
O5—C7—C6	122.28 (14)	C3—C4—H4B	108.6
O6—C7—C6	118.39 (13)	C5—C4—H4B	108.6
C3—O4—H4	109.5	H4A—C4—H4B	107.6
C4—C5—C6	113.75 (12)

N1—C2—C1—O2	−172.80 (15)	C4—C5—C6—C7	−169.33 (16)
N1—C2—C1—O1	8.0 (2)	O3—C3—C4—C5	146.67 (17)
O5—C7—C6—C5	10.5 (2)	O4—C3—C4—C5	−33.9 (2)
O6—C7—C6—C5	−170.40 (15)	C6—C5—C4—C3	−179.68 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O3ⁱ	0.90	2.12	2.9504 (17)	153
N1—H1C···O3ⁱⁱ	0.90	1.99	2.8760 (18)	170
N1—H1A···O5	0.90	1.98	2.7621 (17)	144
O4—H4···O1ⁱⁱⁱ	0.83	1.74	2.5676 (16)	178
O6—H6···O2^iv	0.83	1.73	2.5414 (16)	165

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

(225) Propane-1,3-dicarboxylic acid – Aminoethanoic acid (1/1) top

Crystal data top

C₅H₈O₄·C₂H₅NO₂	F(000) = 440
M_r = 207.18	D_x = 1.446 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3782 reflections
a = 4.8888 (6) Å	θ = 2.0–29.5°
b = 20.859 (2) Å	µ = 0.13 mm⁻¹
c = 10.2664 (13) Å	T = 225 K
β = 114.648 (9)°	Prism, colourless
V = 951.6 (2) Å³	0.32 × 0.17 × 0.10 mm
Z = 4

Data collection top

STOE IPDS 2 diffractometer	1594 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.043
Detector resolution: 6.67 pixels mm^-1	θ_max = 29.2°, θ_min = 2.0°
rotation method scans	h = −5→6
6775 measured reflections	k = −28→24
2558 independent reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: difference Fourier map
wR(F²) = 0.081	H-atom parameters constrained
S = 0.88	w = 1/[σ²(F_o²) + (0.037P)²] where P = (F_o² + 2F_c²)/3
2558 reflections	(Δ/σ)_max < 0.001
130 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₅H₈O₄·C₂H₅NO₂	V = 951.6 (2) Å³
M_r = 207.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.8888 (6) Å	µ = 0.13 mm⁻¹
b = 20.859 (2) Å	T = 225 K
c = 10.2664 (13) Å	0.32 × 0.17 × 0.10 mm
β = 114.648 (9)°

Data collection top

STOE IPDS 2 diffractometer	1594 reflections with I > 2σ(I)
6775 measured reflections	R_int = 0.043
2558 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.081	H-atom parameters constrained
S = 0.88	Δρ_max = 0.21 e Å⁻³
2558 reflections	Δρ_min = −0.18 e Å⁻³
130 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.1297 (3)	0.44519 (5)	0.33441 (10)	0.0314 (3)
O5	0.6253 (3)	0.64046 (5)	0.22218 (10)	0.0346 (3)
O3	0.2033 (3)	0.91561 (5)	−0.03396 (10)	0.0296 (3)
N1	0.5594 (3)	0.52477 (6)	0.33723 (12)	0.0263 (3)
H1A	0.6652	0.5561	0.3190	0.039*
H1B	0.6859	0.4987	0.4058	0.039*
H1C	0.4275	0.5422	0.3673	0.039*
C2	0.3944 (3)	0.48745 (7)	0.20527 (14)	0.0251 (3)
H2A	0.5387	0.4633	0.1809	0.030*
H2B	0.2864	0.5170	0.1261	0.030*
O6	0.8268 (3)	0.59350 (5)	0.09291 (11)	0.0366 (3)
H6	0.8563	0.6012	0.0205	0.055*
O2	0.0402 (3)	0.40272 (6)	0.12133 (12)	0.0403 (3)
C1	0.1715 (3)	0.44119 (7)	0.22204 (14)	0.0247 (3)
C7	0.6820 (4)	0.64190 (7)	0.11764 (14)	0.0249 (3)
O4	0.1061 (3)	0.84624 (5)	0.10478 (13)	0.0423 (3)
H4	0.0407	0.8790	0.1277	0.063*
C5	0.4719 (4)	0.75334 (7)	0.06844 (14)	0.0300 (4)
H5A	0.6403	0.7727	0.1493	0.036*
H5B	0.3267	0.7377	0.1041	0.036*
C6	0.5880 (4)	0.69689 (7)	0.01334 (15)	0.0276 (3)
H6B	0.4301	0.6823	−0.0778	0.033*
H6A	0.7604	0.7107	−0.0049	0.033*
C3	0.2072 (3)	0.86082 (7)	0.00868 (14)	0.0259 (3)
C4	0.3223 (4)	0.80435 (7)	−0.04410 (15)	0.0320 (4)
H4A	0.4675	0.8196	−0.0801	0.038*
H4B	0.1537	0.7849	−0.1247	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0382 (7)	0.0317 (6)	0.0323 (5)	−0.0113 (5)	0.0225 (5)	−0.0052 (4)
O5	0.0512 (8)	0.0277 (6)	0.0338 (5)	0.0037 (5)	0.0266 (5)	0.0051 (4)
O3	0.0376 (7)	0.0217 (5)	0.0332 (5)	0.0002 (5)	0.0183 (5)	0.0016 (4)
N1	0.0308 (7)	0.0234 (6)	0.0295 (6)	−0.0054 (6)	0.0173 (5)	0.0006 (5)
C2	0.0259 (8)	0.0269 (7)	0.0255 (6)	−0.0005 (7)	0.0136 (6)	0.0002 (6)
O6	0.0515 (8)	0.0273 (6)	0.0376 (6)	0.0121 (6)	0.0251 (6)	0.0044 (5)
O2	0.0431 (8)	0.0427 (7)	0.0421 (6)	−0.0173 (6)	0.0249 (6)	−0.0182 (5)
C1	0.0237 (8)	0.0231 (7)	0.0296 (7)	0.0015 (6)	0.0133 (6)	−0.0012 (6)
C7	0.0282 (9)	0.0207 (7)	0.0268 (6)	−0.0022 (6)	0.0124 (6)	−0.0011 (5)
O4	0.0647 (9)	0.0280 (6)	0.0565 (7)	0.0156 (6)	0.0475 (7)	0.0125 (5)
C5	0.0402 (10)	0.0249 (8)	0.0294 (7)	0.0073 (7)	0.0191 (7)	0.0038 (6)
C6	0.0347 (9)	0.0234 (7)	0.0294 (7)	0.0037 (7)	0.0181 (6)	0.0027 (6)
C3	0.0263 (8)	0.0262 (7)	0.0265 (7)	0.0017 (7)	0.0123 (6)	0.0023 (6)
C4	0.0434 (11)	0.0272 (8)	0.0322 (7)	0.0089 (7)	0.0225 (7)	0.0062 (6)

Geometric parameters (Å, º) top

O1—C1	1.2554 (16)	C7—C6	1.5042 (19)
O5—C7	1.2159 (17)	O4—C3	1.3103 (17)
O3—C3	1.2212 (17)	O4—H4	0.8300
N1—C2	1.4766 (18)	C5—C6	1.515 (2)
N1—H1A	0.9000	C5—C4	1.516 (2)
N1—H1B	0.9000	C5—H5A	0.9800
N1—H1C	0.9000	C5—H5B	0.9800
C2—C1	1.518 (2)	C6—H6B	0.9800
C2—H2A	0.9800	C6—H6A	0.9800
C2—H2B	0.9800	C3—C4	1.501 (2)
O6—C7	1.3170 (17)	C4—H4A	0.9800
O6—H6	0.8300	C4—H4B	0.9800
O2—C1	1.2536 (17)

C2—N1—H1A	109.5	C6—C5—H5A	108.9
C2—N1—H1B	109.5	C4—C5—H5A	108.9
H1A—N1—H1B	109.5	C6—C5—H5B	108.9
C2—N1—H1C	109.5	C4—C5—H5B	108.9
H1A—N1—H1C	109.5	H5A—C5—H5B	107.7
H1B—N1—H1C	109.5	C7—C6—C5	112.19 (11)
N1—C2—C1	111.98 (11)	C7—C6—H6B	109.2
N1—C2—H2A	109.2	C5—C6—H6B	109.2
C1—C2—H2A	109.2	C7—C6—H6A	109.2
N1—C2—H2B	109.2	C5—C6—H6A	109.2
C1—C2—H2B	109.2	H6B—C6—H6A	107.9
H2A—C2—H2B	107.9	O3—C3—O4	122.19 (14)
C7—O6—H6	109.5	O3—C3—C4	123.87 (13)
O2—C1—O1	125.24 (14)	O4—C3—C4	113.93 (12)
O2—C1—C2	117.27 (12)	C3—C4—C5	114.22 (11)
O1—C1—C2	117.49 (12)	C3—C4—H4A	108.7
O5—C7—O6	119.33 (13)	C5—C4—H4A	108.7
O5—C7—C6	122.19 (13)	C3—C4—H4B	108.7
O6—C7—C6	118.47 (12)	C5—C4—H4B	108.7
C3—O4—H4	109.5	H4A—C4—H4B	107.6
C6—C5—C4	113.44 (11)

N1—C2—C1—O2	−173.27 (13)	C4—C5—C6—C7	−169.30 (14)
N1—C2—C1—O1	7.84 (19)	O3—C3—C4—C5	146.60 (16)
O5—C7—C6—C5	10.6 (2)	O4—C3—C4—C5	−34.2 (2)
O6—C7—C6—C5	−170.43 (14)	C6—C5—C4—C3	−179.71 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O3ⁱ	0.90	2.11	2.9420 (16)	154
N1—H1C···O3ⁱⁱ	0.90	1.98	2.8716 (16)	170
N1—H1A···O5	0.90	1.99	2.7641 (15)	143
O4—H4···O1ⁱⁱⁱ	0.83	1.74	2.5650 (15)	175
O6—H6···O2^iv	0.83	1.73	2.5417 (15)	165

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

(200) Propane-1,3-dicarboxylic acid – Aminoethanoic acid (1/1) top

Crystal data top

C₅H₈O₄·C₂H₅NO₂	Z = 4
M_r = 207.18	F(000) = 440
Triclinic, P1	D_x = 1.486 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.9155 (7) Å	Cell parameters from 6919 reflections
b = 20.215 (3) Å	θ = 2.0–29.6°
c = 10.1862 (16) Å	µ = 0.13 mm⁻¹
α = 85.578 (14)°	T = 200 K
β = 113.133 (11)°	Prism, colourless
γ = 88.301 (13)°	0.40 × 0.23 × 0.10 mm
V = 926.1 (2) Å³

Data collection top

STOE IPDS 2 diffractometer	2491 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.055
Detector resolution: 6.67 pixels mm^-1	θ_max = 29.2°, θ_min = 2.0°
rotation method scans	h = −6→5
9663 measured reflections	k = −27→27
4312 independent reflections	l = −13→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: difference Fourier map
wR(F²) = 0.081	H-atom parameters constrained
S = 0.89	w = 1/[σ²(F_o²) + (0.0266P)²] where P = (F_o² + 2F_c²)/3
4312 reflections	(Δ/σ)_max = 0.001
259 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₅H₈O₄·C₂H₅NO₂	γ = 88.301 (13)°
M_r = 207.18	V = 926.1 (2) Å³
Triclinic, P1	Z = 4
a = 4.9155 (7) Å	Mo Kα radiation
b = 20.215 (3) Å	µ = 0.13 mm⁻¹
c = 10.1862 (16) Å	T = 200 K
α = 85.578 (14)°	0.40 × 0.23 × 0.10 mm
β = 113.133 (11)°

Data collection top

STOE IPDS 2 diffractometer	2491 reflections with I > 2σ(I)
9663 measured reflections	R_int = 0.055
4312 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.081	H-atom parameters constrained
S = 0.89	Δρ_max = 0.19 e Å⁻³
4312 reflections	Δρ_min = −0.21 e Å⁻³
259 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O23	0.1871 (4)	0.58896 (6)	0.45166 (16)	0.0260 (4)
O25	0.6524 (4)	0.84815 (6)	0.75064 (16)	0.0284 (4)
O26	0.8511 (4)	0.90410 (6)	0.62247 (16)	0.0289 (4)
H26	0.8788	0.9011	0.5468	0.043*
O21	0.1282 (3)	1.05514 (6)	0.82424 (16)	0.0261 (3)
O22	0.0124 (4)	1.09123 (7)	0.59539 (16)	0.0297 (4)
O13	0.7719 (3)	0.08769 (6)	1.01431 (16)	0.0250 (3)
O24	0.0718 (4)	0.65453 (6)	0.59001 (18)	0.0316 (4)
H24	0.0020	0.6197	0.6105	0.047*
O16	0.1845 (4)	0.40381 (7)	0.90921 (17)	0.0328 (4)
H16	0.1809	0.4042	0.9909	0.049*
O14	0.7927 (4)	0.15354 (6)	0.83429 (16)	0.0297 (4)
H14	0.8949	0.1206	0.8291	0.045*
O15	0.4073 (4)	0.34554 (6)	0.80336 (18)	0.0374 (4)
N21	0.5779 (4)	0.97095 (7)	0.84561 (18)	0.0225 (4)
H21A	0.6957	0.9380	0.8351	0.034*
H21B	0.4520	0.9529	0.8822	0.034*
H21C	0.6926	0.9992	0.9064	0.034*
C22	0.4041 (5)	1.00798 (9)	0.7040 (2)	0.0200 (4)
H22A	0.3119	0.9759	0.6331	0.024*
H22B	0.5394	1.0335	0.6720	0.024*
C13	0.7020 (5)	0.14025 (8)	0.9381 (2)	0.0197 (4)
C25	0.4718 (5)	0.74512 (9)	0.5767 (2)	0.0219 (4)
H25A	0.3256	0.7615	0.6133	0.026*
H25B	0.6275	0.7168	0.6557	0.026*
C23	0.1863 (5)	0.64326 (9)	0.4972 (2)	0.0204 (4)
C21	0.1633 (5)	1.05543 (8)	0.7089 (2)	0.0190 (4)
C26	0.6120 (5)	0.80423 (8)	0.5320 (2)	0.0209 (4)
H26A	0.7865	0.7880	0.5151	0.025*
H26B	0.4674	0.8273	0.4408	0.025*
C24	0.3174 (5)	0.70327 (9)	0.4526 (2)	0.0239 (5)
H24A	0.1576	0.7313	0.3749	0.029*
H24B	0.4623	0.6882	0.4139	0.029*
C16	0.5015 (5)	0.30815 (9)	1.0471 (2)	0.0243 (5)
H16A	0.3435	0.2907	1.0748	0.029*
H16B	0.6250	0.3348	1.1237	0.029*
C14	0.5083 (5)	0.19546 (9)	0.9534 (2)	0.0233 (4)
H14A	0.3877	0.1772	1.0042	0.028*
H14B	0.3713	0.2152	0.8571	0.028*
C15	0.6943 (5)	0.24964 (9)	1.0370 (2)	0.0286 (5)
H15A	0.8238	0.2302	1.1349	0.034*
H15B	0.8231	0.2660	0.9889	0.034*
C27	0.7073 (5)	0.85271 (8)	0.6442 (2)	0.0198 (4)
C17	0.3605 (5)	0.35270 (9)	0.9092 (2)	0.0245 (5)
O11	0.8400 (3)	0.55159 (6)	0.65415 (15)	0.0254 (3)
O12	0.9335 (4)	0.58758 (7)	0.86847 (17)	0.0301 (4)
N11	0.4288 (4)	0.47027 (7)	0.66308 (18)	0.0216 (4)
H11A	0.3137	0.4400	0.6832	0.032*
H11B	0.5664	0.4489	0.6396	0.032*
H11C	0.3131	0.4997	0.5882	0.032*
C12	0.5809 (5)	0.50654 (8)	0.7909 (2)	0.0191 (4)
H12A	0.6858	0.4741	0.8753	0.023*
H12B	0.4314	0.5331	0.8108	0.023*
C11	0.8023 (5)	0.55239 (8)	0.7686 (2)	0.0188 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O23	0.0322 (10)	0.0197 (7)	0.0298 (9)	−0.0035 (6)	0.0153 (8)	−0.0067 (6)
O25	0.0419 (10)	0.0231 (7)	0.0283 (9)	−0.0067 (6)	0.0213 (8)	−0.0080 (6)
O26	0.0392 (10)	0.0242 (7)	0.0295 (9)	−0.0116 (6)	0.0189 (8)	−0.0074 (6)
O21	0.0308 (9)	0.0263 (7)	0.0239 (8)	0.0063 (6)	0.0144 (7)	−0.0009 (6)
O22	0.0279 (9)	0.0339 (8)	0.0268 (9)	0.0078 (6)	0.0127 (7)	0.0068 (6)
O13	0.0293 (9)	0.0192 (7)	0.0264 (9)	0.0014 (6)	0.0118 (7)	0.0003 (5)
O24	0.0453 (11)	0.0234 (7)	0.0428 (10)	−0.0147 (7)	0.0328 (9)	−0.0115 (6)
O16	0.0458 (12)	0.0251 (7)	0.0305 (9)	0.0107 (6)	0.0201 (9)	0.0021 (6)
O14	0.0396 (11)	0.0245 (7)	0.0308 (9)	0.0094 (6)	0.0222 (8)	0.0043 (6)
O15	0.0639 (13)	0.0248 (8)	0.0372 (10)	0.0047 (7)	0.0362 (10)	0.0024 (6)
N21	0.0264 (10)	0.0208 (8)	0.0225 (9)	0.0036 (7)	0.0121 (8)	−0.0029 (6)
C22	0.0201 (11)	0.0220 (9)	0.0195 (10)	−0.0014 (7)	0.0093 (9)	−0.0033 (7)
C13	0.0183 (11)	0.0191 (9)	0.0221 (11)	−0.0045 (7)	0.0075 (9)	−0.0062 (7)
C25	0.0258 (12)	0.0215 (9)	0.0215 (11)	−0.0061 (8)	0.0119 (9)	−0.0043 (7)
C23	0.0184 (11)	0.0217 (9)	0.0203 (11)	−0.0031 (7)	0.0066 (9)	−0.0026 (7)
C21	0.0180 (11)	0.0172 (9)	0.0241 (11)	−0.0050 (7)	0.0102 (9)	−0.0036 (7)
C26	0.0251 (12)	0.0194 (9)	0.0201 (11)	−0.0037 (7)	0.0107 (9)	−0.0035 (7)
C24	0.0307 (13)	0.0234 (9)	0.0218 (11)	−0.0083 (8)	0.0137 (10)	−0.0056 (7)
C16	0.0268 (12)	0.0205 (9)	0.0235 (11)	0.0004 (8)	0.0071 (10)	−0.0055 (7)
C14	0.0227 (12)	0.0191 (9)	0.0300 (12)	−0.0010 (7)	0.0122 (10)	−0.0037 (7)
C15	0.0228 (12)	0.0266 (10)	0.0280 (12)	0.0045 (8)	0.0008 (10)	−0.0066 (8)
C27	0.0209 (11)	0.0161 (9)	0.0211 (11)	0.0032 (7)	0.0077 (9)	0.0004 (7)
C17	0.0324 (13)	0.0163 (9)	0.0298 (12)	−0.0050 (8)	0.0171 (11)	−0.0032 (8)
O11	0.0305 (9)	0.0265 (7)	0.0249 (8)	−0.0123 (6)	0.0155 (7)	−0.0069 (6)
O12	0.0331 (10)	0.0333 (8)	0.0306 (9)	−0.0149 (7)	0.0165 (8)	−0.0163 (6)
N11	0.0254 (10)	0.0214 (8)	0.0218 (9)	−0.0076 (7)	0.0128 (8)	−0.0028 (6)
C12	0.0187 (11)	0.0208 (9)	0.0190 (10)	−0.0015 (7)	0.0088 (9)	−0.0020 (7)
C11	0.0158 (10)	0.0169 (9)	0.0238 (11)	0.0005 (7)	0.0084 (9)	−0.0009 (7)

Geometric parameters (Å, º) top

O23—C23	1.225 (2)	C25—H25B	0.9900
O25—C27	1.214 (2)	C23—C24	1.512 (3)
O26—C27	1.326 (2)	C26—C27	1.505 (3)
O26—H26	0.8400	C26—H26A	0.9900
O21—C21	1.252 (2)	C26—H26B	0.9900
O22—C21	1.256 (2)	C24—H24A	0.9900
O13—C13	1.221 (2)	C24—H24B	0.9900
O24—C23	1.306 (2)	C16—C17	1.506 (3)
O24—H24	0.8400	C16—C15	1.529 (3)
O16—C17	1.328 (3)	C16—H16A	0.9900
O16—H16	0.8400	C16—H16B	0.9900
O14—C13	1.313 (2)	C14—C15	1.533 (3)
O14—H14	0.8400	C14—H14A	0.9900
O15—C17	1.205 (3)	C14—H14B	0.9900
N21—C22	1.482 (2)	C15—H15A	0.9900
N21—H21A	0.9100	C15—H15B	0.9900
N21—H21B	0.9100	O11—C11	1.252 (2)
N21—H21C	0.9100	O12—C11	1.257 (2)
C22—C21	1.520 (3)	N11—C12	1.486 (3)
C22—H22A	0.9900	N11—H11A	0.9100
C22—H22B	0.9900	N11—H11B	0.9100
C13—C14	1.502 (3)	N11—H11C	0.9100
C25—C26	1.524 (2)	C12—C11	1.522 (3)
C25—C24	1.530 (3)	C12—H12A	0.9900
C25—H25A	0.9900	C12—H12B	0.9900

C27—O26—H26	109.5	C25—C24—H24B	109.1
C23—O24—H24	109.5	H24A—C24—H24B	107.8
C17—O16—H16	109.5	C17—C16—C15	113.30 (18)
C13—O14—H14	109.5	C17—C16—H16A	108.9
C22—N21—H21A	109.5	C15—C16—H16A	108.9
C22—N21—H21B	109.5	C17—C16—H16B	108.9
H21A—N21—H21B	109.5	C15—C16—H16B	108.9
C22—N21—H21C	109.5	H16A—C16—H16B	107.7
H21A—N21—H21C	109.5	C13—C14—C15	111.21 (18)
H21B—N21—H21C	109.5	C13—C14—H14A	109.4
N21—C22—C21	112.13 (16)	C15—C14—H14A	109.4
N21—C22—H22A	109.2	C13—C14—H14B	109.4
C21—C22—H22A	109.2	C15—C14—H14B	109.4
N21—C22—H22B	109.2	H14A—C14—H14B	108.0
C21—C22—H22B	109.2	C16—C15—C14	112.17 (19)
H22A—C22—H22B	107.9	C16—C15—H15A	109.2
O13—C13—O14	122.23 (18)	C14—C15—H15A	109.2
O13—C13—C14	124.05 (18)	C16—C15—H15B	109.2
O14—C13—C14	113.72 (16)	C14—C15—H15B	109.2
C26—C25—C24	112.25 (16)	H15A—C15—H15B	107.9
C26—C25—H25A	109.2	O25—C27—O26	118.69 (18)
C24—C25—H25A	109.2	O25—C27—C26	123.50 (17)
C26—C25—H25B	109.2	O26—C27—C26	117.78 (17)
C24—C25—H25B	109.2	O15—C17—O16	119.58 (19)
H25A—C25—H25B	107.9	O15—C17—C16	123.7 (2)
O23—C23—O24	122.74 (17)	O16—C17—C16	116.62 (18)
O23—C23—C24	123.6 (2)	C12—N11—H11A	109.5
O24—C23—C24	113.64 (17)	C12—N11—H11B	109.5
O21—C21—O22	125.30 (19)	H11A—N11—H11B	109.5
O21—C21—C22	117.85 (17)	C12—N11—H11C	109.5
O22—C21—C22	116.85 (17)	H11A—N11—H11C	109.5
C27—C26—C25	111.92 (17)	H11B—N11—H11C	109.5
C27—C26—H26A	109.2	N11—C12—C11	111.60 (16)
C25—C26—H26A	109.2	N11—C12—H12A	109.3
C27—C26—H26B	109.2	C11—C12—H12A	109.3
C25—C26—H26B	109.2	N11—C12—H12B	109.3
H26A—C26—H26B	107.9	C11—C12—H12B	109.3
C23—C24—C25	112.57 (17)	H12A—C12—H12B	108.0
C23—C24—H24A	109.1	O11—C11—O12	125.71 (18)
C25—C24—H24A	109.1	O11—C11—C12	117.77 (17)
C23—C24—H24B	109.1	O12—C11—C12	116.51 (18)

N21—C22—C21—O21	−4.0 (2)	C17—C16—C15—C14	−75.0 (2)
N21—C22—C21—O22	176.98 (16)	C13—C14—C15—C16	176.98 (18)
C24—C25—C26—C27	168.16 (18)	C25—C26—C27—O25	−6.6 (3)
O23—C23—C24—C25	−142.3 (2)	C25—C26—C27—O26	175.47 (18)
O24—C23—C24—C25	37.5 (3)	C15—C16—C17—O15	−4.1 (3)
C26—C25—C24—C23	178.14 (18)	C15—C16—C17—O16	178.57 (19)
O13—C13—C14—C15	99.0 (2)	N11—C12—C11—O11	−3.6 (2)
O14—C13—C14—C15	−80.7 (2)	N11—C12—C11—O12	176.97 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O14—H14···O21ⁱ	0.84	1.74	2.580 (2)	176
O16—H16···O12ⁱⁱ	0.84	1.75	2.565 (2)	164
N11—H11A···O15	0.91	2.12	2.827 (2)	134
N11—H11B···O23ⁱⁱⁱ	0.91	1.96	2.860 (2)	168
N11—H11C···O23	0.91	2.11	2.971 (2)	158
O24—H24···O11^iv	0.84	1.72	2.5636 (18)	176
O26—H26···O22^v	0.84	1.73	2.555 (2)	167
N21—H21A···O25	0.91	2.05	2.798 (2)	139
N21—H21B···O13ⁱⁱ	0.91	1.96	2.861 (2)	172
N21—H21C···O13^vi	0.91	2.14	2.984 (2)	155

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

(175) Propane-1,3-dicarboxylic acid – Aminoethanoic acid (1/1) top

Crystal data top

C₅H₈O₄·C₂H₅NO₂	Z = 4
M_r = 207.18	F(000) = 440
Triclinic, P1	D_x = 1.490 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.9098 (7) Å	Cell parameters from 7461 reflections
b = 20.194 (3) Å	θ = 2.1–29.6°
c = 10.1777 (15) Å	µ = 0.13 mm⁻¹
α = 85.571 (13)°	T = 175 K
β = 113.118 (10)°	Prism, colourless
γ = 88.306 (12)°	0.40 × 0.23 × 0.10 mm
V = 923.3 (2) Å³

Data collection top

STOE IPDS 2 diffractometer	2580 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.052
Detector resolution: 6.67 pixels mm^-1	θ_max = 29.2°, θ_min = 2.0°
rotation method scans	h = −6→5
9568 measured reflections	k = −27→27
4319 independent reflections	l = −13→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: difference Fourier map
wR(F²) = 0.088	H-atom parameters constrained
S = 0.89	w = 1/[σ²(F_o²) + (0.0329P)²] where P = (F_o² + 2F_c²)/3
4319 reflections	(Δ/σ)_max < 0.001
259 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₅H₈O₄·C₂H₅NO₂	γ = 88.306 (12)°
M_r = 207.18	V = 923.3 (2) Å³
Triclinic, P1	Z = 4
a = 4.9098 (7) Å	Mo Kα radiation
b = 20.194 (3) Å	µ = 0.13 mm⁻¹
c = 10.1777 (15) Å	T = 175 K
α = 85.571 (13)°	0.40 × 0.23 × 0.10 mm
β = 113.118 (10)°

Data collection top

STOE IPDS 2 diffractometer	2580 reflections with I > 2σ(I)
9568 measured reflections	R_int = 0.052
4319 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 0.89	Δρ_max = 0.22 e Å⁻³
4319 reflections	Δρ_min = −0.23 e Å⁻³
259 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O23	0.1870 (4)	0.58898 (6)	0.45114 (16)	0.0223 (3)
O25	0.6532 (4)	0.84810 (6)	0.75156 (17)	0.0248 (3)
O26	0.8537 (4)	0.90432 (6)	0.62332 (17)	0.0253 (4)
H26	0.8731	0.9023	0.5453	0.038*
O21	0.1280 (4)	1.05536 (6)	0.82397 (16)	0.0232 (3)
O22	0.0102 (4)	1.09092 (7)	0.59471 (17)	0.0263 (4)
O13	0.7721 (3)	0.08762 (6)	1.01479 (16)	0.0206 (3)
O24	0.0731 (4)	0.65463 (6)	0.59004 (18)	0.0271 (4)
H24	0.0011	0.6199	0.6096	0.041*
O16	0.1825 (4)	0.40414 (7)	0.90858 (17)	0.0281 (4)
H16	0.1714	0.4036	0.9889	0.042*
O14	0.7902 (4)	0.15354 (7)	0.83352 (17)	0.0262 (4)
H14	0.8959	0.1209	0.8296	0.039*
O15	0.4050 (4)	0.34553 (7)	0.80242 (18)	0.0324 (4)
N21	0.5783 (4)	0.97136 (7)	0.84576 (19)	0.0194 (4)
H21A	0.6999	0.9390	0.8359	0.029*
H21B	0.4525	0.9525	0.8815	0.029*
H21C	0.6895	1.0000	0.9071	0.029*
C22	0.4044 (5)	1.00819 (9)	0.7039 (2)	0.0174 (4)
H22A	0.3135	0.9760	0.6330	0.021*
H22B	0.5395	1.0340	0.6719	0.021*
C13	0.6991 (5)	0.14026 (9)	0.9372 (2)	0.0167 (4)
C25	0.4744 (5)	0.74496 (9)	0.5774 (2)	0.0189 (4)
H25A	0.3283	0.7612	0.6144	0.023*
H25B	0.6304	0.7165	0.6561	0.023*
C23	0.1879 (5)	0.64342 (9)	0.4973 (2)	0.0174 (4)
C21	0.1618 (5)	1.05536 (9)	0.7083 (2)	0.0172 (4)
C26	0.6149 (5)	0.80440 (9)	0.5328 (2)	0.0181 (4)
H26A	0.7902	0.7883	0.5163	0.022*
H26B	0.4704	0.8274	0.4414	0.022*
C24	0.3189 (5)	0.70327 (9)	0.4523 (2)	0.0204 (4)
H24A	0.1590	0.7314	0.3748	0.025*
H24B	0.4636	0.6882	0.4135	0.025*
C16	0.4997 (5)	0.30820 (9)	1.0471 (2)	0.0213 (4)
H16A	0.3413	0.2907	1.0747	0.026*
H16B	0.6229	0.3349	1.1238	0.026*
C14	0.5064 (5)	0.19536 (9)	0.9533 (2)	0.0201 (4)
H14A	0.3859	0.1769	1.0042	0.024*
H14B	0.3689	0.2153	0.8571	0.024*
C15	0.6933 (5)	0.24963 (9)	1.0374 (2)	0.0251 (5)
H15A	0.8221	0.2302	1.1355	0.030*
H15B	0.8229	0.2659	0.9897	0.030*
C27	0.7086 (5)	0.85301 (8)	0.6451 (2)	0.0173 (4)
C17	0.3590 (5)	0.35270 (9)	0.9092 (2)	0.0202 (4)
O11	0.8391 (3)	0.55165 (6)	0.65370 (16)	0.0223 (3)
O12	0.9358 (4)	0.58730 (7)	0.86881 (17)	0.0259 (4)
N11	0.4277 (4)	0.47053 (7)	0.66306 (18)	0.0187 (4)
H11A	0.3117	0.4404	0.6830	0.028*
H11B	0.5652	0.4490	0.6395	0.028*
H11C	0.3126	0.5001	0.5882	0.028*
C12	0.5803 (5)	0.50660 (9)	0.7910 (2)	0.0166 (4)
H12A	0.6848	0.4740	0.8753	0.020*
H12B	0.4311	0.5333	0.8111	0.020*
C11	0.8031 (5)	0.55238 (8)	0.7686 (2)	0.0168 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O23	0.0276 (9)	0.0155 (7)	0.0266 (9)	−0.0038 (6)	0.0128 (7)	−0.0062 (5)
O25	0.0364 (10)	0.0207 (7)	0.0244 (9)	−0.0062 (6)	0.0183 (8)	−0.0074 (5)
O26	0.0346 (10)	0.0213 (7)	0.0245 (9)	−0.0103 (6)	0.0151 (8)	−0.0065 (6)
O21	0.0272 (9)	0.0230 (7)	0.0217 (8)	0.0057 (6)	0.0130 (7)	−0.0014 (6)
O22	0.0259 (9)	0.0286 (8)	0.0247 (9)	0.0073 (6)	0.0125 (7)	0.0066 (6)
O13	0.0233 (9)	0.0159 (6)	0.0222 (8)	0.0001 (5)	0.0089 (7)	−0.0001 (5)
O24	0.0394 (10)	0.0194 (7)	0.0370 (10)	−0.0121 (7)	0.0286 (9)	−0.0097 (6)
O16	0.0381 (11)	0.0225 (7)	0.0254 (9)	0.0085 (6)	0.0160 (8)	0.0018 (6)
O14	0.0339 (10)	0.0221 (7)	0.0269 (9)	0.0089 (6)	0.0187 (8)	0.0041 (6)
O15	0.0544 (12)	0.0215 (7)	0.0330 (10)	0.0028 (7)	0.0309 (9)	0.0018 (6)
N21	0.0239 (10)	0.0165 (8)	0.0199 (9)	0.0024 (6)	0.0113 (8)	−0.0019 (6)
C22	0.0172 (11)	0.0188 (9)	0.0167 (10)	−0.0025 (7)	0.0070 (8)	−0.0028 (7)
C13	0.0172 (11)	0.0159 (8)	0.0176 (11)	−0.0030 (7)	0.0071 (9)	−0.0036 (7)
C25	0.0197 (11)	0.0187 (9)	0.0195 (10)	−0.0039 (7)	0.0088 (9)	−0.0024 (7)
C23	0.0174 (11)	0.0184 (9)	0.0161 (10)	−0.0018 (7)	0.0065 (9)	−0.0008 (7)
C21	0.0164 (11)	0.0158 (9)	0.0220 (11)	−0.0044 (7)	0.0100 (9)	−0.0036 (7)
C26	0.0219 (11)	0.0166 (9)	0.0179 (10)	−0.0026 (7)	0.0094 (9)	−0.0041 (7)
C24	0.0254 (12)	0.0201 (9)	0.0196 (11)	−0.0070 (8)	0.0120 (10)	−0.0055 (7)
C16	0.0217 (12)	0.0185 (9)	0.0203 (11)	0.0000 (8)	0.0043 (9)	−0.0052 (7)
C14	0.0199 (11)	0.0173 (9)	0.0250 (11)	−0.0009 (7)	0.0108 (9)	−0.0035 (7)
C15	0.0211 (12)	0.0223 (10)	0.0262 (12)	0.0045 (8)	0.0031 (10)	−0.0060 (8)
C27	0.0159 (10)	0.0147 (8)	0.0192 (11)	0.0020 (7)	0.0052 (9)	−0.0005 (7)
C17	0.0235 (12)	0.0155 (9)	0.0250 (12)	−0.0040 (8)	0.0128 (10)	−0.0027 (7)
O11	0.0278 (9)	0.0226 (7)	0.0217 (8)	−0.0101 (6)	0.0144 (7)	−0.0051 (5)
O12	0.0278 (9)	0.0294 (8)	0.0259 (9)	−0.0126 (6)	0.0136 (7)	−0.0141 (6)
N11	0.0233 (10)	0.0171 (8)	0.0192 (9)	−0.0069 (7)	0.0116 (8)	−0.0025 (6)
C12	0.0164 (11)	0.0186 (9)	0.0157 (10)	−0.0016 (7)	0.0075 (8)	−0.0018 (7)
C11	0.0164 (10)	0.0143 (8)	0.0209 (11)	0.0007 (7)	0.0091 (9)	−0.0003 (7)

Geometric parameters (Å, º) top

O23—C23	1.228 (2)	C25—H25B	0.9900
O25—C27	1.214 (3)	C23—C24	1.509 (3)
O26—C27	1.328 (2)	C26—C27	1.506 (3)
O26—H26	0.8400	C26—H26A	0.9900
O21—C21	1.252 (3)	C26—H26B	0.9900
O22—C21	1.253 (2)	C24—H24A	0.9900
O13—C13	1.228 (2)	C24—H24B	0.9900
O24—C23	1.305 (3)	C16—C17	1.504 (3)
O24—H24	0.8400	C16—C15	1.529 (3)
O16—C17	1.331 (3)	C16—H16A	0.9900
O16—H16	0.8400	C16—H16B	0.9900
O14—C13	1.311 (2)	C14—C15	1.537 (3)
O14—H14	0.8400	C14—H14A	0.9900
O15—C17	1.212 (3)	C14—H14B	0.9900
N21—C22	1.482 (3)	C15—H15A	0.9900
N21—H21A	0.9100	C15—H15B	0.9900
N21—H21B	0.9100	O11—C11	1.251 (2)
N21—H21C	0.9100	O12—C11	1.256 (2)
C22—C21	1.520 (3)	N11—C12	1.483 (3)
C22—H22A	0.9900	N11—H11A	0.9100
C22—H22B	0.9900	N11—H11B	0.9100
C13—C14	1.499 (3)	N11—H11C	0.9100
C25—C26	1.527 (3)	C12—C11	1.525 (3)
C25—C24	1.534 (3)	C12—H12A	0.9900
C25—H25A	0.9900	C12—H12B	0.9900

C27—O26—H26	109.5	C25—C24—H24B	109.2
C23—O24—H24	109.5	H24A—C24—H24B	107.9
C17—O16—H16	109.5	C17—C16—C15	113.39 (18)
C13—O14—H14	109.5	C17—C16—H16A	108.9
C22—N21—H21A	109.5	C15—C16—H16A	108.9
C22—N21—H21B	109.5	C17—C16—H16B	108.9
H21A—N21—H21B	109.5	C15—C16—H16B	108.9
C22—N21—H21C	109.5	H16A—C16—H16B	107.7
H21A—N21—H21C	109.5	C13—C14—C15	111.32 (18)
H21B—N21—H21C	109.5	C13—C14—H14A	109.4
N21—C22—C21	112.08 (16)	C15—C14—H14A	109.4
N21—C22—H22A	109.2	C13—C14—H14B	109.4
C21—C22—H22A	109.2	C15—C14—H14B	109.4
N21—C22—H22B	109.2	H14A—C14—H14B	108.0
C21—C22—H22B	109.2	C16—C15—C14	112.01 (18)
H22A—C22—H22B	107.9	C16—C15—H15A	109.2
O13—C13—O14	122.14 (18)	C14—C15—H15A	109.2
O13—C13—C14	123.87 (18)	C16—C15—H15B	109.2
O14—C13—C14	113.97 (16)	C14—C15—H15B	109.2
C26—C25—C24	112.14 (17)	H15A—C15—H15B	107.9
C26—C25—H25A	109.2	O25—C27—O26	119.15 (18)
C24—C25—H25A	109.2	O25—C27—C26	123.38 (17)
C26—C25—H25B	109.2	O26—C27—C26	117.45 (18)
C24—C25—H25B	109.2	O15—C17—O16	119.13 (18)
H25A—C25—H25B	107.9	O15—C17—C16	123.97 (19)
O23—C23—O24	122.57 (17)	O16—C17—C16	116.85 (18)
O23—C23—C24	123.5 (2)	C12—N11—H11A	109.5
O24—C23—C24	113.88 (17)	C12—N11—H11B	109.5
O21—C21—O22	125.3 (2)	H11A—N11—H11B	109.5
O21—C21—C22	117.76 (18)	C12—N11—H11C	109.5
O22—C21—C22	116.92 (18)	H11A—N11—H11C	109.5
C27—C26—C25	111.87 (17)	H11B—N11—H11C	109.5
C27—C26—H26A	109.2	N11—C12—C11	111.48 (16)
C25—C26—H26A	109.2	N11—C12—H12A	109.3
C27—C26—H26B	109.2	C11—C12—H12A	109.3
C25—C26—H26B	109.2	N11—C12—H12B	109.3
H26A—C26—H26B	107.9	C11—C12—H12B	109.3
C23—C24—C25	112.18 (17)	H12A—C12—H12B	108.0
C23—C24—H24A	109.2	O11—C11—O12	125.87 (18)
C25—C24—H24A	109.2	O11—C11—C12	117.66 (17)
C23—C24—H24B	109.2	O12—C11—C12	116.47 (18)

N21—C22—C21—O21	−3.4 (2)	C17—C16—C15—C14	−74.9 (2)
N21—C22—C21—O22	177.07 (17)	C13—C14—C15—C16	176.58 (18)
C24—C25—C26—C27	167.68 (18)	C25—C26—C27—O25	−6.3 (3)
O23—C23—C24—C25	−142.6 (2)	C25—C26—C27—O26	175.11 (18)
O24—C23—C24—C25	37.7 (3)	C15—C16—C17—O15	−3.7 (3)
C26—C25—C24—C23	178.32 (18)	C15—C16—C17—O16	178.74 (18)
O13—C13—C14—C15	98.0 (2)	N11—C12—C11—O11	−3.2 (2)
O14—C13—C14—C15	−80.7 (2)	N11—C12—C11—O12	177.22 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O14—H14···O21ⁱ	0.84	1.74	2.579 (2)	178
O16—H16···O12ⁱⁱ	0.84	1.74	2.567 (2)	166
N11—H11A···O15	0.91	2.12	2.826 (2)	133
N11—H11B···O23ⁱⁱⁱ	0.91	1.96	2.860 (2)	168
N11—H11C···O23	0.91	2.10	2.967 (2)	158
O24—H24···O11^iv	0.84	1.73	2.5655 (18)	176
O26—H26···O22^v	0.84	1.73	2.552 (2)	166
N21—H21A···O25	0.91	2.07	2.800 (2)	137
N21—H21B···O13ⁱⁱ	0.91	1.95	2.859 (2)	172
N21—H21C···O13^vi	0.91	2.12	2.974 (2)	156

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

(150) Propane-1,3-dicarboxylic acid – Aminoethanoic acid (1/1) top

Crystal data top

C₅H₈O₄·C₂H₅NO₂	Z = 4
M_r = 207.18	F(000) = 440
Triclinic, P1	D_x = 1.496 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.9021 (7) Å	Cell parameters from 7886 reflections
b = 20.167 (3) Å	θ = 2.1–29.6°
c = 10.1686 (15) Å	µ = 0.13 mm⁻¹
α = 85.540 (11)°	T = 150 K
β = 113.122 (10)°	Prism, colourless
γ = 88.270 (11)°	0.40 × 0.23 × 0.10 mm
V = 919.7 (2) Å³

Data collection top

STOE IPDS 2 diffractometer	2840 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.040
Detector resolution: 6.67 pixels mm^-1	θ_max = 29.2°, θ_min = 2.0°
rotation method scans	h = −6→5
10066 measured reflections	k = −27→27
4417 independent reflections	l = −13→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: difference Fourier map
wR(F²) = 0.077	H-atom parameters constrained
S = 0.88	w = 1/[σ²(F_o²) + (0.0327P)²] where P = (F_o² + 2F_c²)/3
4417 reflections	(Δ/σ)_max = 0.001
259 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₅H₈O₄·C₂H₅NO₂	γ = 88.270 (11)°
M_r = 207.18	V = 919.7 (2) Å³
Triclinic, P1	Z = 4
a = 4.9021 (7) Å	Mo Kα radiation
b = 20.167 (3) Å	µ = 0.13 mm⁻¹
c = 10.1686 (15) Å	T = 150 K
α = 85.540 (11)°	0.40 × 0.23 × 0.10 mm
β = 113.122 (10)°

Data collection top

STOE IPDS 2 diffractometer	2840 reflections with I > 2σ(I)
10066 measured reflections	R_int = 0.040
4417 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.077	H-atom parameters constrained
S = 0.88	Δρ_max = 0.21 e Å⁻³
4417 reflections	Δρ_min = −0.20 e Å⁻³
259 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O23	0.1874 (3)	0.58914 (5)	0.45078 (12)	0.0203 (3)
O25	0.6546 (3)	0.84812 (5)	0.75242 (13)	0.0223 (3)
O26	0.8549 (3)	0.90476 (5)	0.62412 (13)	0.0228 (3)
H26	0.8755	0.9028	0.5463	0.034*
O21	0.1276 (3)	1.05551 (5)	0.82410 (12)	0.0206 (2)
O22	0.0071 (3)	1.09063 (5)	0.59387 (13)	0.0232 (3)
O13	0.7716 (3)	0.08766 (5)	1.01507 (12)	0.0190 (2)
O24	0.0737 (3)	0.65465 (5)	0.59016 (14)	0.0243 (3)
H24	−0.0057	0.6204	0.6065	0.036*
O16	0.1809 (3)	0.40439 (5)	0.90802 (13)	0.0255 (3)
H16	0.1707	0.4040	0.9886	0.038*
O14	0.7880 (3)	0.15347 (5)	0.83294 (13)	0.0232 (3)
H14	0.8872	0.1201	0.8266	0.035*
O15	0.4039 (3)	0.34547 (5)	0.80201 (14)	0.0290 (3)
N21	0.5793 (3)	0.97142 (6)	0.84584 (14)	0.0179 (3)
H21A	0.7037	0.9394	0.8364	0.027*
H21B	0.4531	0.9520	0.8807	0.027*
H21C	0.6879	1.0002	0.9076	0.027*
C22	0.4054 (4)	1.00833 (7)	0.70355 (17)	0.0160 (3)
H22A	0.3151	0.9761	0.6325	0.019*
H22B	0.5407	1.0343	0.6718	0.019*
C13	0.6982 (4)	0.14032 (7)	0.93729 (16)	0.0157 (3)
C25	0.4768 (4)	0.74507 (7)	0.57750 (17)	0.0168 (3)
H25A	0.3307	0.7613	0.6146	0.020*
H25B	0.6328	0.7164	0.6562	0.020*
C23	0.1886 (4)	0.64362 (7)	0.49715 (17)	0.0160 (3)
C21	0.1611 (4)	1.05547 (7)	0.70778 (17)	0.0155 (3)
C26	0.6178 (4)	0.80449 (7)	0.53373 (17)	0.0173 (3)
H26A	0.7941	0.7884	0.5178	0.021*
H26B	0.4738	0.8275	0.4419	0.021*
C24	0.3205 (4)	0.70337 (7)	0.45289 (18)	0.0197 (3)
H24A	0.1606	0.7317	0.3753	0.024*
H24B	0.4653	0.6882	0.4140	0.024*
C16	0.4986 (4)	0.30835 (7)	1.04724 (18)	0.0202 (3)
H16A	0.3402	0.2911	1.0752	0.024*
H16B	0.6230	0.3351	1.1237	0.024*
C14	0.5041 (4)	0.19555 (7)	0.95314 (18)	0.0186 (3)
H14A	0.3831	0.1771	1.0038	0.022*
H14B	0.3668	0.2155	0.8567	0.022*
C15	0.6904 (4)	0.24967 (8)	1.03731 (19)	0.0233 (4)
H15A	0.8191	0.2301	1.1355	0.028*
H15B	0.8208	0.2659	0.9898	0.028*
C27	0.7102 (4)	0.85318 (7)	0.64558 (17)	0.0159 (3)
C17	0.3573 (4)	0.35294 (7)	0.90864 (18)	0.0196 (3)
O11	0.8392 (3)	0.55172 (5)	0.65368 (12)	0.0202 (2)
O12	0.9381 (3)	0.58701 (5)	0.86944 (13)	0.0231 (3)
N11	0.4275 (3)	0.47064 (6)	0.66303 (14)	0.0176 (3)
H11A	0.3137	0.4399	0.6834	0.026*
H11B	0.5653	0.4497	0.6386	0.026*
H11C	0.3097	0.5002	0.5885	0.026*
C12	0.5797 (4)	0.50657 (7)	0.79090 (17)	0.0161 (3)
H12A	0.6837	0.4738	0.8753	0.019*
H12B	0.4301	0.5334	0.8108	0.019*
C11	0.8035 (3)	0.55227 (7)	0.76915 (17)	0.0149 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O23	0.0243 (7)	0.0161 (5)	0.0228 (6)	−0.0029 (4)	0.0112 (5)	−0.0050 (4)
O25	0.0321 (7)	0.0192 (5)	0.0213 (6)	−0.0043 (5)	0.0160 (6)	−0.0054 (4)
O26	0.0321 (7)	0.0192 (5)	0.0223 (6)	−0.0088 (5)	0.0151 (6)	−0.0058 (4)
O21	0.0226 (6)	0.0212 (5)	0.0190 (6)	0.0041 (4)	0.0100 (5)	−0.0014 (4)
O22	0.0222 (7)	0.0267 (6)	0.0207 (6)	0.0051 (5)	0.0102 (5)	0.0047 (4)
O13	0.0216 (6)	0.0154 (5)	0.0199 (6)	0.0002 (4)	0.0083 (5)	−0.0004 (4)
O24	0.0339 (7)	0.0184 (5)	0.0329 (7)	−0.0106 (5)	0.0247 (6)	−0.0090 (5)
O16	0.0354 (8)	0.0208 (6)	0.0229 (7)	0.0077 (5)	0.0155 (6)	0.0011 (4)
O14	0.0309 (7)	0.0200 (5)	0.0229 (6)	0.0071 (5)	0.0168 (6)	0.0035 (4)
O15	0.0480 (9)	0.0201 (6)	0.0300 (7)	0.0020 (5)	0.0281 (7)	0.0010 (5)
N21	0.0205 (7)	0.0163 (6)	0.0179 (7)	0.0030 (5)	0.0091 (6)	−0.0017 (5)
C22	0.0165 (8)	0.0170 (7)	0.0159 (7)	−0.0020 (5)	0.0076 (6)	−0.0025 (5)
C13	0.0153 (8)	0.0151 (7)	0.0159 (8)	−0.0027 (6)	0.0047 (7)	−0.0038 (5)
C25	0.0205 (8)	0.0165 (7)	0.0163 (8)	−0.0041 (6)	0.0096 (7)	−0.0037 (5)
C23	0.0145 (8)	0.0174 (7)	0.0150 (8)	−0.0013 (5)	0.0046 (6)	−0.0017 (5)
C21	0.0151 (8)	0.0146 (7)	0.0182 (8)	−0.0037 (5)	0.0078 (6)	−0.0029 (5)
C26	0.0213 (8)	0.0161 (7)	0.0168 (8)	−0.0031 (6)	0.0095 (7)	−0.0030 (5)
C24	0.0249 (9)	0.0193 (7)	0.0178 (8)	−0.0065 (6)	0.0108 (7)	−0.0047 (6)
C16	0.0221 (9)	0.0162 (7)	0.0213 (8)	−0.0001 (6)	0.0072 (7)	−0.0045 (6)
C14	0.0190 (8)	0.0155 (7)	0.0223 (8)	−0.0009 (6)	0.0091 (7)	−0.0027 (6)
C15	0.0185 (9)	0.0206 (8)	0.0252 (9)	0.0031 (6)	0.0025 (7)	−0.0051 (6)
C27	0.0153 (8)	0.0128 (7)	0.0184 (8)	0.0013 (5)	0.0056 (6)	−0.0003 (5)
C17	0.0247 (9)	0.0143 (7)	0.0241 (9)	−0.0038 (6)	0.0139 (7)	−0.0031 (6)
O11	0.0243 (7)	0.0207 (5)	0.0199 (6)	−0.0086 (4)	0.0124 (5)	−0.0043 (4)
O12	0.0247 (7)	0.0261 (6)	0.0233 (6)	−0.0103 (5)	0.0123 (5)	−0.0117 (4)
N11	0.0214 (7)	0.0163 (6)	0.0185 (7)	−0.0063 (5)	0.0110 (6)	−0.0022 (5)
C12	0.0157 (8)	0.0176 (7)	0.0164 (7)	−0.0015 (6)	0.0078 (6)	−0.0023 (5)
C11	0.0136 (8)	0.0136 (7)	0.0185 (8)	0.0011 (5)	0.0077 (6)	−0.0009 (5)

Geometric parameters (Å, º) top

O23—C23	1.2280 (18)	C25—H25B	0.9900
O25—C27	1.2176 (19)	C23—C24	1.505 (2)
O26—C27	1.3279 (18)	C26—C27	1.503 (2)
O26—H26	0.8400	C26—H26A	0.9900
O21—C21	1.2563 (19)	C26—H26B	0.9900
O22—C21	1.2518 (19)	C24—H24A	0.9900
O13—C13	1.2271 (17)	C24—H24B	0.9900
O24—C23	1.3056 (19)	C16—C17	1.508 (2)
O24—H24	0.8400	C16—C15	1.523 (2)
O16—C17	1.328 (2)	C16—H16A	0.9900
O16—H16	0.8400	C16—H16B	0.9900
O14—C13	1.3117 (19)	C14—C15	1.533 (2)
O14—H14	0.8400	C14—H14A	0.9900
O15—C17	1.212 (2)	C14—H14B	0.9900
N21—C22	1.483 (2)	C15—H15A	0.9900
N21—H21A	0.9100	C15—H15B	0.9900
N21—H21B	0.9100	O11—C11	1.2541 (19)
N21—H21C	0.9100	O12—C11	1.2557 (19)
C22—C21	1.523 (2)	N11—C12	1.480 (2)
C22—H22A	0.9900	N11—H11A	0.9100
C22—H22B	0.9900	N11—H11B	0.9100
C13—C14	1.502 (2)	N11—H11C	0.9100
C25—C26	1.523 (2)	C12—C11	1.524 (2)
C25—C24	1.530 (2)	C12—H12A	0.9900
C25—H25A	0.9900	C12—H12B	0.9900

C27—O26—H26	109.5	C25—C24—H24B	109.1
C23—O24—H24	109.5	H24A—C24—H24B	107.8
C17—O16—H16	109.5	C17—C16—C15	113.27 (14)
C13—O14—H14	109.5	C17—C16—H16A	108.9
C22—N21—H21A	109.5	C15—C16—H16A	108.9
C22—N21—H21B	109.5	C17—C16—H16B	108.9
H21A—N21—H21B	109.5	C15—C16—H16B	108.9
C22—N21—H21C	109.5	H16A—C16—H16B	107.7
H21A—N21—H21C	109.5	C13—C14—C15	111.24 (14)
H21B—N21—H21C	109.5	C13—C14—H14A	109.4
N21—C22—C21	111.96 (13)	C15—C14—H14A	109.4
N21—C22—H22A	109.2	C13—C14—H14B	109.4
C21—C22—H22A	109.2	C15—C14—H14B	109.4
N21—C22—H22B	109.2	H14A—C14—H14B	108.0
C21—C22—H22B	109.2	C16—C15—C14	112.36 (14)
H22A—C22—H22B	107.9	C16—C15—H15A	109.1
O13—C13—O14	122.15 (14)	C14—C15—H15A	109.1
O13—C13—C14	123.87 (14)	C16—C15—H15B	109.1
O14—C13—C14	113.97 (12)	C14—C15—H15B	109.1
C26—C25—C24	112.64 (13)	H15A—C15—H15B	107.9
C26—C25—H25A	109.1	O25—C27—O26	119.01 (14)
C24—C25—H25A	109.1	O25—C27—C26	123.29 (13)
C26—C25—H25B	109.1	O26—C27—C26	117.69 (14)
C24—C25—H25B	109.1	O15—C17—O16	119.42 (14)
H25A—C25—H25B	107.8	O15—C17—C16	123.78 (15)
O23—C23—O24	122.42 (13)	O16—C17—C16	116.75 (14)
O23—C23—C24	123.66 (15)	C12—N11—H11A	109.5
O24—C23—C24	113.92 (13)	C12—N11—H11B	109.5
O22—C21—O21	125.27 (15)	H11A—N11—H11B	109.5
O22—C21—C22	117.00 (14)	C12—N11—H11C	109.5
O21—C21—C22	117.72 (13)	H11A—N11—H11C	109.5
C27—C26—C25	112.15 (13)	H11B—N11—H11C	109.5
C27—C26—H26A	109.2	N11—C12—C11	111.57 (13)
C25—C26—H26A	109.2	N11—C12—H12A	109.3
C27—C26—H26B	109.2	C11—C12—H12A	109.3
C25—C26—H26B	109.2	N11—C12—H12B	109.3
H26A—C26—H26B	107.9	C11—C12—H12B	109.3
C23—C24—C25	112.62 (13)	H12A—C12—H12B	108.0
C23—C24—H24A	109.1	O11—C11—O12	125.60 (14)
C25—C24—H24A	109.1	O11—C11—C12	117.52 (13)
C23—C24—H24B	109.1	O12—C11—C12	116.87 (14)

N21—C22—C21—O22	177.79 (13)	C17—C16—C15—C14	−74.51 (18)
N21—C22—C21—O21	−2.99 (18)	C13—C14—C15—C16	176.54 (14)
C24—C25—C26—C27	167.31 (14)	C25—C26—C27—O25	−5.9 (2)
O23—C23—C24—C25	−142.48 (16)	C25—C26—C27—O26	175.38 (14)
O24—C23—C24—C25	37.6 (2)	C15—C16—C17—O15	−4.0 (2)
C26—C25—C24—C23	178.41 (14)	C15—C16—C17—O16	178.47 (14)
O13—C13—C14—C15	97.87 (18)	N11—C12—C11—O11	−2.93 (19)
O14—C13—C14—C15	−81.22 (17)	N11—C12—C11—O12	177.57 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O14—H14···O21ⁱ	0.84	1.74	2.5745 (16)	174
O16—H16···O12ⁱⁱ	0.84	1.74	2.5658 (17)	166
N11—H11A···O15	0.91	2.11	2.8238 (16)	135
N11—H11B···O23ⁱⁱⁱ	0.91	1.96	2.8554 (18)	169
N11—H11C···O23	0.91	2.10	2.9644 (17)	158
O24—H24···O11^iv	0.84	1.72	2.5626 (14)	176
O26—H26···O22^v	0.84	1.73	2.5550 (16)	166
N21—H21A···O25	0.91	2.07	2.7944 (17)	136
N21—H21B···O13ⁱⁱ	0.91	1.95	2.8551 (17)	171
N21—H21C···O13^vi	0.91	2.11	2.9719 (18)	157

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

(125) Propane-1,3-dicarboxylic acid – Aminoethanoic acid (1/1) top

Crystal data top

C₅H₈O₄·C₂H₅NO₂	Z = 4
M_r = 207.18	F(000) = 440
Triclinic, P1	D_x = 1.501 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.8952 (6) Å	Cell parameters from 8370 reflections
b = 20.151 (3) Å	θ = 2.1–29.6°
c = 10.1585 (13) Å	µ = 0.13 mm⁻¹
α = 85.518 (11)°	T = 125 K
β = 113.088 (9)°	Prism, colourless
γ = 88.264 (11)°	0.40 × 0.23 × 0.10 mm
V = 916.9 (2) Å³

Data collection top

STOE IPDS 2 diffractometer	2935 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.038
Detector resolution: 6.67 pixels mm^-1	θ_max = 29.2°, θ_min = 2.0°
rotation method scans	h = −6→5
9997 measured reflections	k = −27→27
4391 independent reflections	l = −13→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: difference Fourier map
wR(F²) = 0.075	H-atom parameters constrained
S = 0.90	w = 1/[σ²(F_o²) + (0.0331P)²] where P = (F_o² + 2F_c²)/3
4391 reflections	(Δ/σ)_max = 0.001
259 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₅H₈O₄·C₂H₅NO₂	γ = 88.264 (11)°
M_r = 207.18	V = 916.9 (2) Å³
Triclinic, P1	Z = 4
a = 4.8952 (6) Å	Mo Kα radiation
b = 20.151 (3) Å	µ = 0.13 mm⁻¹
c = 10.1585 (13) Å	T = 125 K
α = 85.518 (11)°	0.40 × 0.23 × 0.10 mm
β = 113.088 (9)°

Data collection top

STOE IPDS 2 diffractometer	2935 reflections with I > 2σ(I)
9997 measured reflections	R_int = 0.038
4391 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 0.90	Δρ_max = 0.23 e Å⁻³
4391 reflections	Δρ_min = −0.20 e Å⁻³
259 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O23	0.1879 (3)	0.58911 (5)	0.45029 (12)	0.0173 (2)
O25	0.6557 (3)	0.84815 (5)	0.75302 (12)	0.0188 (2)
O26	0.8564 (3)	0.90507 (5)	0.62477 (12)	0.0192 (2)
H26	0.8812	0.9026	0.5480	0.029*
O21	0.1277 (3)	1.05564 (5)	0.82429 (12)	0.0176 (2)
O22	0.0047 (3)	1.09042 (5)	0.59311 (12)	0.0196 (2)
O13	0.7715 (3)	0.08758 (5)	1.01545 (12)	0.0163 (2)
O24	0.0747 (3)	0.65473 (5)	0.59045 (13)	0.0208 (3)
H24	−0.0037	0.6204	0.6074	0.031*
O16	0.1792 (3)	0.40479 (5)	0.90748 (13)	0.0218 (3)
H16	0.1693	0.4046	0.9882	0.033*
O14	0.7857 (3)	0.15346 (5)	0.83223 (12)	0.0199 (2)
H14	0.8885	0.1204	0.8271	0.030*
O15	0.4030 (3)	0.34543 (5)	0.80176 (13)	0.0248 (3)
N21	0.5804 (3)	0.97171 (6)	0.84609 (14)	0.0152 (3)
H21A	0.7024	0.9391	0.8366	0.023*
H21B	0.4542	0.9530	0.8821	0.023*
H21C	0.6917	1.0005	0.9071	0.023*
C22	0.4059 (3)	1.00839 (7)	0.70358 (16)	0.0137 (3)
H22A	0.3164	0.9760	0.6327	0.016*
H22B	0.5408	1.0345	0.6717	0.016*
C13	0.6967 (3)	0.14032 (7)	0.93711 (16)	0.0133 (3)
C25	0.4781 (4)	0.74509 (7)	0.57783 (16)	0.0151 (3)
H25A	0.3315	0.7613	0.6149	0.018*
H25B	0.6344	0.7164	0.6566	0.018*
C23	0.1894 (3)	0.64365 (7)	0.49710 (16)	0.0142 (3)
C21	0.1601 (3)	1.05532 (7)	0.70766 (16)	0.0136 (3)
C26	0.6191 (4)	0.80469 (7)	0.53377 (16)	0.0149 (3)
H26A	0.7955	0.7886	0.5176	0.018*
H26B	0.4748	0.8278	0.4421	0.018*
C24	0.3224 (4)	0.70350 (7)	0.45288 (17)	0.0168 (3)
H24A	0.1628	0.7319	0.3751	0.020*
H24B	0.4678	0.6882	0.4142	0.020*
C16	0.4975 (4)	0.30849 (7)	1.04730 (17)	0.0172 (3)
H16A	0.3387	0.2914	1.0754	0.021*
H16B	0.6223	0.3352	1.1237	0.021*
C14	0.5022 (4)	0.19550 (7)	0.95298 (17)	0.0158 (3)
H14A	0.3807	0.1770	1.0035	0.019*
H14B	0.3651	0.2156	0.8565	0.019*
C15	0.6889 (4)	0.24962 (7)	1.03760 (18)	0.0198 (3)
H15A	0.8168	0.2299	1.1359	0.024*
H15B	0.8204	0.2658	0.9904	0.024*
C27	0.7117 (3)	0.85331 (7)	0.64638 (16)	0.0139 (3)
C17	0.3562 (4)	0.35311 (7)	0.90847 (17)	0.0166 (3)
O11	0.8392 (3)	0.55171 (5)	0.65348 (12)	0.0172 (2)
O12	0.9398 (3)	0.58671 (5)	0.86977 (12)	0.0197 (2)
N11	0.4250 (3)	0.47085 (6)	0.66249 (14)	0.0150 (3)
H11A	0.3073	0.4409	0.6821	0.023*
H11B	0.5625	0.4490	0.6390	0.023*
H11C	0.3109	0.5007	0.5875	0.023*
C12	0.5791 (3)	0.50673 (7)	0.79119 (16)	0.0136 (3)
H12A	0.6823	0.4739	0.8756	0.016*
H12B	0.4301	0.5338	0.8111	0.016*
C11	0.8048 (3)	0.55207 (7)	0.76937 (16)	0.0135 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O23	0.0199 (6)	0.0139 (5)	0.0194 (6)	−0.0023 (4)	0.0087 (5)	−0.0043 (4)
O25	0.0263 (6)	0.0168 (5)	0.0176 (6)	−0.0036 (4)	0.0126 (5)	−0.0041 (4)
O26	0.0264 (7)	0.0163 (5)	0.0197 (6)	−0.0069 (4)	0.0133 (5)	−0.0050 (4)
O21	0.0199 (6)	0.0188 (5)	0.0159 (6)	0.0028 (4)	0.0092 (5)	−0.0012 (4)
O22	0.0188 (6)	0.0216 (5)	0.0180 (6)	0.0037 (4)	0.0085 (5)	0.0041 (4)
O13	0.0182 (6)	0.0130 (5)	0.0170 (6)	0.0001 (4)	0.0066 (5)	−0.0007 (4)
O24	0.0291 (7)	0.0156 (5)	0.0282 (6)	−0.0091 (5)	0.0210 (6)	−0.0072 (4)
O16	0.0301 (7)	0.0175 (5)	0.0195 (6)	0.0063 (4)	0.0126 (6)	0.0007 (4)
O14	0.0268 (7)	0.0164 (5)	0.0201 (6)	0.0056 (4)	0.0144 (5)	0.0023 (4)
O15	0.0412 (8)	0.0178 (5)	0.0246 (6)	0.0015 (5)	0.0238 (6)	0.0006 (4)
N21	0.0173 (7)	0.0144 (6)	0.0148 (6)	0.0023 (5)	0.0075 (5)	−0.0014 (4)
C22	0.0138 (7)	0.0151 (6)	0.0123 (7)	−0.0007 (5)	0.0052 (6)	−0.0016 (5)
C13	0.0129 (7)	0.0128 (6)	0.0141 (7)	−0.0027 (5)	0.0049 (6)	−0.0033 (5)
C25	0.0183 (8)	0.0149 (7)	0.0152 (7)	−0.0040 (5)	0.0094 (6)	−0.0035 (5)
C23	0.0117 (7)	0.0160 (7)	0.0135 (7)	−0.0008 (5)	0.0036 (6)	−0.0014 (5)
C21	0.0129 (7)	0.0127 (6)	0.0168 (7)	−0.0040 (5)	0.0069 (6)	−0.0032 (5)
C26	0.0178 (8)	0.0144 (7)	0.0141 (7)	−0.0022 (5)	0.0080 (6)	−0.0016 (5)
C24	0.0210 (8)	0.0157 (7)	0.0164 (7)	−0.0050 (6)	0.0099 (7)	−0.0033 (5)
C16	0.0186 (8)	0.0147 (7)	0.0172 (8)	−0.0004 (5)	0.0054 (6)	−0.0047 (5)
C14	0.0159 (8)	0.0140 (7)	0.0182 (8)	−0.0001 (5)	0.0077 (6)	−0.0016 (5)
C15	0.0161 (8)	0.0180 (7)	0.0206 (8)	0.0020 (6)	0.0019 (7)	−0.0048 (6)
C27	0.0124 (7)	0.0115 (6)	0.0152 (7)	0.0012 (5)	0.0031 (6)	−0.0007 (5)
C17	0.0206 (8)	0.0120 (6)	0.0204 (8)	−0.0046 (5)	0.0109 (7)	−0.0033 (5)
O11	0.0210 (6)	0.0179 (5)	0.0169 (6)	−0.0071 (4)	0.0111 (5)	−0.0041 (4)
O12	0.0200 (6)	0.0229 (5)	0.0197 (6)	−0.0079 (4)	0.0097 (5)	−0.0094 (4)
N11	0.0182 (7)	0.0139 (6)	0.0156 (6)	−0.0048 (5)	0.0091 (5)	−0.0016 (4)
C12	0.0131 (7)	0.0145 (6)	0.0137 (7)	−0.0016 (5)	0.0058 (6)	−0.0021 (5)
C11	0.0130 (7)	0.0119 (6)	0.0161 (7)	0.0004 (5)	0.0064 (6)	−0.0010 (5)

Geometric parameters (Å, º) top

O23—C23	1.2303 (18)	C25—H25B	0.9900
O25—C27	1.2150 (19)	C23—C24	1.5073 (19)
O26—C27	1.3299 (17)	C26—C27	1.506 (2)
O26—H26	0.8400	C26—H26A	0.9900
O21—C21	1.2561 (19)	C26—H26B	0.9900
O22—C21	1.2561 (18)	C24—H24A	0.9900
O13—C13	1.2297 (17)	C24—H24B	0.9900
O24—C23	1.3069 (19)	C16—C17	1.508 (2)
O24—H24	0.8400	C16—C15	1.522 (2)
O16—C17	1.3315 (19)	C16—H16A	0.9900
O16—H16	0.8400	C16—H16B	0.9900
O14—C13	1.3122 (18)	C14—C15	1.534 (2)
O14—H14	0.8400	C14—H14A	0.9900
O15—C17	1.213 (2)	C14—H14B	0.9900
N21—C22	1.4820 (19)	C15—H15A	0.9900
N21—H21A	0.9100	C15—H15B	0.9900
N21—H21B	0.9100	O11—C11	1.2535 (18)
N21—H21C	0.9100	O12—C11	1.2549 (18)
C22—C21	1.523 (2)	N11—C12	1.4860 (19)
C22—H22A	0.9900	N11—H11A	0.9100
C22—H22B	0.9900	N11—H11B	0.9100
C13—C14	1.501 (2)	N11—H11C	0.9100
C25—C26	1.5256 (19)	C12—C11	1.525 (2)
C25—C24	1.530 (2)	C12—H12A	0.9900
C25—H25A	0.9900	C12—H12B	0.9900

C27—O26—H26	109.5	C25—C24—H24B	109.1
C23—O24—H24	109.5	H24A—C24—H24B	107.8
C17—O16—H16	109.5	C17—C16—C15	113.34 (13)
C13—O14—H14	109.5	C17—C16—H16A	108.9
C22—N21—H21A	109.5	C15—C16—H16A	108.9
C22—N21—H21B	109.5	C17—C16—H16B	108.9
H21A—N21—H21B	109.5	C15—C16—H16B	108.9
C22—N21—H21C	109.5	H16A—C16—H16B	107.7
H21A—N21—H21C	109.5	C13—C14—C15	111.18 (13)
H21B—N21—H21C	109.5	C13—C14—H14A	109.4
N21—C22—C21	111.89 (12)	C15—C14—H14A	109.4
N21—C22—H22A	109.2	C13—C14—H14B	109.4
C21—C22—H22A	109.2	C15—C14—H14B	109.4
N21—C22—H22B	109.2	H14A—C14—H14B	108.0
C21—C22—H22B	109.2	C16—C15—C14	112.47 (13)
H22A—C22—H22B	107.9	C16—C15—H15A	109.1
O13—C13—O14	122.16 (14)	C14—C15—H15A	109.1
O13—C13—C14	123.89 (13)	C16—C15—H15B	109.1
O14—C13—C14	113.94 (12)	C14—C15—H15B	109.1
C26—C25—C24	112.40 (12)	H15A—C15—H15B	107.8
C26—C25—H25A	109.1	O25—C27—O26	119.09 (13)
C24—C25—H25A	109.1	O25—C27—C26	123.40 (13)
C26—C25—H25B	109.1	O26—C27—C26	117.50 (13)
C24—C25—H25B	109.1	O15—C17—O16	119.43 (14)
H25A—C25—H25B	107.9	O15—C17—C16	123.68 (14)
O23—C23—O24	122.54 (13)	O16—C17—C16	116.84 (13)
O23—C23—C24	123.56 (15)	C12—N11—H11A	109.5
O24—C23—C24	113.90 (13)	C12—N11—H11B	109.5
O22—C21—O21	125.25 (15)	H11A—N11—H11B	109.5
O22—C21—C22	117.00 (13)	C12—N11—H11C	109.5
O21—C21—C22	117.75 (13)	H11A—N11—H11C	109.5
C27—C26—C25	111.91 (12)	H11B—N11—H11C	109.5
C27—C26—H26A	109.2	N11—C12—C11	111.46 (12)
C25—C26—H26A	109.2	N11—C12—H12A	109.3
C27—C26—H26B	109.2	C11—C12—H12A	109.3
C25—C26—H26B	109.2	N11—C12—H12B	109.3
H26A—C26—H26B	107.9	C11—C12—H12B	109.3
C23—C24—C25	112.47 (13)	H12A—C12—H12B	108.0
C23—C24—H24A	109.1	O11—C11—O12	125.71 (14)
C25—C24—H24A	109.1	O11—C11—C12	117.59 (13)
C23—C24—H24B	109.1	O12—C11—C12	116.70 (13)

N21—C22—C21—O22	177.84 (12)	C17—C16—C15—C14	−74.23 (17)
N21—C22—C21—O21	−2.58 (18)	C13—C14—C15—C16	176.32 (13)
C24—C25—C26—C27	167.46 (13)	C25—C26—C27—O25	−6.1 (2)
O23—C23—C24—C25	−142.69 (16)	C25—C26—C27—O26	175.42 (13)
O24—C23—C24—C25	37.30 (19)	C15—C16—C17—O15	−4.1 (2)
C26—C25—C24—C23	178.60 (13)	C15—C16—C17—O16	178.32 (13)
O13—C13—C14—C15	97.45 (17)	N11—C12—C11—O11	−2.49 (18)
O14—C13—C14—C15	−81.62 (16)	N11—C12—C11—O12	177.39 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O14—H14···O21ⁱ	0.84	1.74	2.5739 (16)	175
O16—H16···O12ⁱⁱ	0.84	1.74	2.5644 (16)	166
N11—H11A···O15	0.91	2.13	2.8245 (15)	133
N11—H11B···O23ⁱⁱⁱ	0.91	1.96	2.8537 (18)	168
N11—H11C···O23	0.91	2.09	2.9564 (17)	159
O24—H24···O11^iv	0.84	1.72	2.5623 (14)	176
O26—H26···O22^v	0.84	1.73	2.5539 (16)	167
N21—H21A···O25	0.91	2.06	2.7956 (17)	137
N21—H21B···O13ⁱⁱ	0.91	1.95	2.8522 (17)	172
N21—H21C···O13^vi	0.91	2.11	2.9639 (17)	156

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

(100) Propane-1,3-dicarboxylic acid – Aminoethanoic acid (1/1) top

Crystal data top

C₅H₈O₄·C₂H₅NO₂	Z = 4
M_r = 207.18	F(000) = 440
Triclinic, P1	D_x = 1.505 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.8884 (7) Å	Cell parameters from 8917 reflections
b = 20.136 (3) Å	θ = 2.1–29.6°
c = 10.1518 (15) Å	µ = 0.13 mm⁻¹
α = 85.486 (13)°	T = 100 K
β = 113.065 (10)°	Prism, colourless
γ = 88.263 (12)°	0.40 × 0.23 × 0.10 mm
V = 914.5 (2) Å³

Data collection top

STOE IPDS 2 diffractometer	2766 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.052
Detector resolution: 6.67 pixels mm^-1	θ_max = 29.2°, θ_min = 2.0°
rotation method scans	h = −6→5
8816 measured reflections	k = −27→27
4247 independent reflections	l = −13→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.053	Hydrogen site location: difference Fourier map
wR(F²) = 0.097	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0367P)²] where P = (F_o² + 2F_c²)/3
4247 reflections	(Δ/σ)_max = 0.001
259 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₅H₈O₄·C₂H₅NO₂	γ = 88.263 (12)°
M_r = 207.18	V = 914.5 (2) Å³
Triclinic, P1	Z = 4
a = 4.8884 (7) Å	Mo Kα radiation
b = 20.136 (3) Å	µ = 0.13 mm⁻¹
c = 10.1518 (15) Å	T = 100 K
α = 85.486 (13)°	0.40 × 0.23 × 0.10 mm
β = 113.065 (10)°

Data collection top

STOE IPDS 2 diffractometer	2766 reflections with I > 2σ(I)
8816 measured reflections	R_int = 0.052
4247 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 0.98	Δρ_max = 0.31 e Å⁻³
4247 reflections	Δρ_min = −0.29 e Å⁻³
259 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O23	0.1875 (4)	0.58907 (6)	0.44968 (16)	0.0138 (3)
O25	0.6555 (4)	0.84827 (7)	0.75344 (17)	0.0154 (3)
O26	0.8581 (4)	0.90525 (7)	0.62556 (17)	0.0151 (3)
H26	0.8961	0.9012	0.5527	0.023*
O21	0.1280 (4)	1.05580 (7)	0.82434 (16)	0.0145 (3)
O22	0.0018 (4)	1.09019 (7)	0.59227 (17)	0.0161 (3)
O13	0.7712 (3)	0.08755 (6)	1.01603 (16)	0.0129 (3)
O24	0.0754 (4)	0.65477 (7)	0.59062 (18)	0.0164 (3)
H24	0.0083	0.6196	0.6125	0.025*
O16	0.1782 (4)	0.40501 (7)	0.90676 (17)	0.0170 (3)
H16	0.1737	0.4056	0.9885	0.025*
O14	0.7839 (4)	0.15336 (7)	0.83151 (17)	0.0159 (3)
H14	0.8916	0.1208	0.8282	0.024*
O15	0.4030 (4)	0.34543 (7)	0.80174 (18)	0.0197 (4)
N21	0.5811 (4)	0.97199 (8)	0.84592 (19)	0.0124 (4)
H21A	0.7074	0.9402	0.8369	0.019*
H21B	0.4552	0.9522	0.8809	0.019*
H21C	0.6881	1.0011	0.9075	0.019*
C22	0.4058 (5)	1.00861 (9)	0.7031 (2)	0.0107 (4)
H22A	0.3168	0.9761	0.6324	0.013*
H22B	0.5406	1.0348	0.6710	0.013*
C13	0.6952 (5)	0.14024 (9)	0.9368 (2)	0.0105 (4)
C25	0.4806 (5)	0.74504 (9)	0.5787 (2)	0.0114 (4)
H25A	0.3343	0.7610	0.6162	0.014*
H25B	0.6376	0.7163	0.6570	0.014*
C23	0.1899 (5)	0.64358 (9)	0.4969 (2)	0.0111 (4)
C21	0.1586 (5)	1.05554 (9)	0.7067 (2)	0.0104 (4)
C26	0.6206 (5)	0.80486 (9)	0.5342 (2)	0.0117 (4)
H26A	0.7977	0.7890	0.5182	0.014*
H26B	0.4758	0.8279	0.4424	0.014*
C24	0.3238 (5)	0.70367 (9)	0.4524 (2)	0.0129 (4)
H24A	0.1643	0.7322	0.3748	0.015*
H24B	0.4693	0.6884	0.4136	0.015*
C16	0.4952 (5)	0.30859 (9)	1.0473 (2)	0.0133 (4)
H16A	0.3355	0.2915	1.0749	0.016*
H16B	0.6194	0.3354	1.1238	0.016*
C14	0.5003 (5)	0.19553 (9)	0.9527 (2)	0.0120 (4)
H14A	0.3781	0.1770	1.0030	0.014*
H14B	0.3636	0.2158	0.8562	0.014*
C15	0.6883 (5)	0.24948 (10)	1.0379 (2)	0.0158 (4)
H15A	0.8156	0.2296	1.1363	0.019*
H15B	0.8206	0.2656	0.9911	0.019*
C27	0.7122 (5)	0.85358 (9)	0.6466 (2)	0.0106 (4)
C17	0.3553 (5)	0.35312 (9)	0.9077 (2)	0.0123 (4)
O11	0.8386 (4)	0.55177 (7)	0.65326 (16)	0.0139 (3)
O12	0.9420 (4)	0.58647 (7)	0.87026 (17)	0.0158 (3)
N11	0.4247 (4)	0.47105 (8)	0.66252 (19)	0.0123 (4)
H11A	0.3045	0.4416	0.6817	0.018*
H11B	0.5623	0.4486	0.6400	0.018*
H11C	0.3129	0.5010	0.5871	0.018*
C12	0.5787 (5)	0.50689 (9)	0.7909 (2)	0.0106 (4)
H12A	0.6816	0.4740	0.8754	0.013*
H12B	0.4295	0.5341	0.8107	0.013*
C11	0.8053 (5)	0.55222 (9)	0.7695 (2)	0.0102 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O23	0.0166 (8)	0.0109 (7)	0.0153 (8)	−0.0032 (5)	0.0071 (7)	−0.0045 (5)
O25	0.0215 (9)	0.0136 (7)	0.0153 (8)	−0.0030 (6)	0.0113 (7)	−0.0037 (5)
O26	0.0203 (9)	0.0134 (7)	0.0149 (8)	−0.0055 (6)	0.0099 (7)	−0.0037 (5)
O21	0.0166 (8)	0.0154 (7)	0.0132 (8)	0.0024 (6)	0.0080 (7)	−0.0008 (5)
O22	0.0156 (8)	0.0177 (7)	0.0153 (8)	0.0030 (6)	0.0074 (7)	0.0022 (5)
O13	0.0139 (8)	0.0104 (6)	0.0135 (8)	0.0001 (5)	0.0046 (7)	−0.0004 (5)
O24	0.0226 (9)	0.0125 (7)	0.0226 (9)	−0.0079 (6)	0.0166 (7)	−0.0061 (6)
O16	0.0244 (10)	0.0142 (7)	0.0147 (8)	0.0048 (6)	0.0109 (7)	0.0001 (5)
O14	0.0214 (9)	0.0119 (7)	0.0172 (8)	0.0045 (6)	0.0118 (7)	0.0027 (5)
O15	0.0315 (10)	0.0133 (7)	0.0207 (9)	0.0019 (6)	0.0180 (8)	0.0007 (6)
N21	0.0146 (9)	0.0100 (7)	0.0131 (9)	0.0019 (6)	0.0065 (8)	−0.0006 (6)
C22	0.0121 (10)	0.0113 (9)	0.0108 (10)	−0.0008 (7)	0.0066 (8)	−0.0014 (7)
C13	0.0096 (10)	0.0101 (8)	0.0116 (10)	−0.0024 (7)	0.0035 (9)	−0.0035 (7)
C25	0.0100 (10)	0.0134 (9)	0.0110 (10)	−0.0022 (7)	0.0042 (8)	−0.0020 (7)
C23	0.0090 (10)	0.0135 (9)	0.0098 (10)	0.0002 (7)	0.0028 (8)	−0.0011 (7)
C21	0.0090 (10)	0.0095 (8)	0.0142 (10)	−0.0033 (7)	0.0057 (9)	−0.0017 (7)
C26	0.0145 (11)	0.0097 (8)	0.0130 (10)	−0.0018 (7)	0.0075 (9)	−0.0025 (7)
C24	0.0157 (11)	0.0130 (9)	0.0120 (10)	−0.0038 (7)	0.0070 (9)	−0.0030 (7)
C16	0.0135 (11)	0.0112 (9)	0.0128 (10)	−0.0002 (7)	0.0024 (9)	−0.0030 (7)
C14	0.0144 (11)	0.0101 (9)	0.0132 (10)	−0.0001 (7)	0.0074 (9)	−0.0012 (7)
C15	0.0128 (11)	0.0155 (9)	0.0157 (11)	0.0020 (8)	0.0018 (9)	−0.0038 (7)
C27	0.0087 (10)	0.0091 (8)	0.0115 (10)	0.0016 (7)	0.0018 (8)	0.0002 (7)
C17	0.0127 (11)	0.0094 (9)	0.0155 (11)	−0.0032 (7)	0.0063 (9)	−0.0017 (7)
O11	0.0169 (9)	0.0139 (7)	0.0136 (8)	−0.0050 (6)	0.0083 (7)	−0.0033 (5)
O12	0.0162 (8)	0.0182 (7)	0.0156 (8)	−0.0067 (6)	0.0075 (7)	−0.0079 (6)
N11	0.0159 (9)	0.0116 (8)	0.0123 (9)	−0.0040 (6)	0.0082 (8)	−0.0016 (6)
C12	0.0121 (11)	0.0117 (9)	0.0097 (10)	−0.0017 (7)	0.0058 (8)	−0.0020 (7)
C11	0.0092 (10)	0.0092 (8)	0.0137 (10)	0.0011 (7)	0.0061 (8)	−0.0004 (7)

Geometric parameters (Å, º) top

O23—C23	1.230 (2)	C25—H25B	0.9900
O25—C27	1.218 (3)	C23—C24	1.514 (3)
O26—C27	1.329 (2)	C26—C27	1.506 (3)
O26—H26	0.8400	C26—H26A	0.9900
O21—C21	1.261 (3)	C26—H26B	0.9900
O22—C21	1.251 (3)	C24—H24A	0.9900
O13—C13	1.232 (2)	C24—H24B	0.9900
O24—C23	1.309 (3)	C16—C17	1.511 (3)
O24—H24	0.8400	C16—C15	1.528 (3)
O16—C17	1.334 (3)	C16—H16A	0.9900
O16—H16	0.8400	C16—H16B	0.9900
O14—C13	1.313 (3)	C14—C15	1.536 (3)
O14—H14	0.8400	C14—H14A	0.9900
O15—C17	1.206 (3)	C14—H14B	0.9900
N21—C22	1.483 (3)	C15—H15A	0.9900
N21—H21A	0.9100	C15—H15B	0.9900
N21—H21B	0.9100	O11—C11	1.254 (3)
N21—H21C	0.9100	O12—C11	1.254 (3)
C22—C21	1.525 (3)	N11—C12	1.483 (3)
C22—H22A	0.9900	N11—H11A	0.9100
C22—H22B	0.9900	N11—H11B	0.9100
C13—C14	1.502 (3)	N11—H11C	0.9100
C25—C26	1.526 (3)	C12—C11	1.525 (3)
C25—C24	1.537 (3)	C12—H12A	0.9900
C25—H25A	0.9900	C12—H12B	0.9900

C27—O26—H26	109.5	C25—C24—H24B	109.2
C23—O24—H24	109.5	H24A—C24—H24B	107.9
C17—O16—H16	109.5	C17—C16—C15	113.01 (18)
C13—O14—H14	109.5	C17—C16—H16A	109.0
C22—N21—H21A	109.5	C15—C16—H16A	109.0
C22—N21—H21B	109.5	C17—C16—H16B	109.0
H21A—N21—H21B	109.5	C15—C16—H16B	109.0
C22—N21—H21C	109.5	H16A—C16—H16B	107.8
H21A—N21—H21C	109.5	C13—C14—C15	111.04 (18)
H21B—N21—H21C	109.5	C13—C14—H14A	109.4
N21—C22—C21	112.03 (17)	C15—C14—H14A	109.4
N21—C22—H22A	109.2	C13—C14—H14B	109.4
C21—C22—H22A	109.2	C15—C14—H14B	109.4
N21—C22—H22B	109.2	H14A—C14—H14B	108.0
C21—C22—H22B	109.2	C16—C15—C14	112.16 (18)
H22A—C22—H22B	107.9	C16—C15—H15A	109.2
O13—C13—O14	122.31 (19)	C14—C15—H15A	109.2
O13—C13—C14	123.72 (19)	C16—C15—H15B	109.2
O14—C13—C14	113.96 (16)	C14—C15—H15B	109.2
C26—C25—C24	111.99 (17)	H15A—C15—H15B	107.9
C26—C25—H25A	109.2	O25—C27—O26	119.10 (18)
C24—C25—H25A	109.2	O25—C27—C26	123.30 (17)
C26—C25—H25B	109.2	O26—C27—C26	117.60 (18)
C24—C25—H25B	109.2	O15—C17—O16	119.60 (19)
H25A—C25—H25B	107.9	O15—C17—C16	124.0 (2)
O23—C23—O24	122.71 (18)	O16—C17—C16	116.40 (19)
O23—C23—C24	123.5 (2)	C12—N11—H11A	109.5
O24—C23—C24	113.84 (17)	C12—N11—H11B	109.5
O22—C21—O21	125.5 (2)	H11A—N11—H11B	109.5
O22—C21—C22	117.20 (18)	C12—N11—H11C	109.5
O21—C21—C22	117.27 (18)	H11A—N11—H11C	109.5
C27—C26—C25	111.88 (17)	H11B—N11—H11C	109.5
C27—C26—H26A	109.2	N11—C12—C11	111.66 (17)
C25—C26—H26A	109.2	N11—C12—H12A	109.3
C27—C26—H26B	109.2	C11—C12—H12A	109.3
C25—C26—H26B	109.2	N11—C12—H12B	109.3
H26A—C26—H26B	107.9	C11—C12—H12B	109.3
C23—C24—C25	112.07 (17)	H12A—C12—H12B	107.9
C23—C24—H24A	109.2	O12—C11—O11	125.93 (19)
C25—C24—H24A	109.2	O12—C11—C12	116.87 (18)
C23—C24—H24B	109.2	O11—C11—C12	117.20 (18)

N21—C22—C21—O22	178.23 (17)	C17—C16—C15—C14	−74.2 (2)
N21—C22—C21—O21	−2.3 (2)	C13—C14—C15—C16	176.23 (18)
C24—C25—C26—C27	167.06 (18)	C25—C26—C27—O25	−6.2 (3)
O23—C23—C24—C25	−142.8 (2)	C25—C26—C27—O26	174.87 (18)
O24—C23—C24—C25	37.3 (3)	C15—C16—C17—O15	−4.0 (3)
C26—C25—C24—C23	178.91 (18)	C15—C16—C17—O16	178.57 (17)
O13—C13—C14—C15	96.8 (2)	N11—C12—C11—O12	177.91 (18)
O14—C13—C14—C15	−82.0 (2)	N11—C12—C11—O11	−2.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O14—H14···O21ⁱ	0.84	1.73	2.571 (2)	177
O16—H16···O12ⁱⁱ	0.84	1.75	2.568 (2)	164
N11—H11A···O15	0.91	2.14	2.824 (2)	131
N11—H11B···O23ⁱⁱⁱ	0.91	1.96	2.851 (2)	168
N11—H11C···O23	0.91	2.08	2.953 (2)	160
O24—H24···O11^iv	0.84	1.72	2.5611 (19)	175
O26—H26···O22^v	0.84	1.73	2.555 (2)	168
N21—H21A···O25	0.91	2.08	2.793 (2)	135
N21—H21B···O13ⁱⁱ	0.91	1.95	2.849 (2)	171
N21—H21C···O13^vi	0.91	2.10	2.961 (2)	158

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

Experimental details

	(300)	(275)	(250)	(225)
Crystal data
Chemical formula	C₅H₈O₄·C₂H₅NO₂	C₅H₈O₄·C₂H₅NO₂	C₅H₈O₄·C₂H₅NO₂	C₅H₈O₄·C₂H₅NO₂
M_r	207.18	207.18	207.18	207.18
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, P2₁/c	Monoclinic, P2₁/c	Monoclinic, P2₁/c
Temperature (K)	300	275	250	225
a, b, c (Å)	4.9110 (7), 20.922 (3), 10.2744 (15)	4.9022 (7), 20.901 (3), 10.2730 (15)	4.8960 (6), 20.878 (2), 10.2701 (13)	4.8888 (6), 20.859 (2), 10.2664 (13)
α, β, γ (°)	90, 114.586 (10), 90	90, 114.60 (1), 90	90, 114.634 (9), 90	90, 114.648 (9), 90
V (Å³)	959.9 (2)	957.0 (2)	954.3 (2)	951.6 (2)
Z	4	4	4	4
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.13	0.13	0.13	0.13
Crystal size (mm)	0.32 × 0.17 × 0.10	0.32 × 0.17 × 0.10	0.32 × 0.17 × 0.10	0.32 × 0.17 × 0.10

Data collection
Diffractometer	STOE IPDS 2 diffractometer	STOE IPDS 2 diffractometer	STOE IPDS 2 diffractometer	STOE IPDS 2 diffractometer
Absorption correction	–	–	–	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6828, 2578, 1421	6792, 2570, 1461	6775, 2562, 1535	6775, 2558, 1594
R_int	0.046	0.047	0.045	0.043
(sin θ/λ)_max (Å⁻¹)	0.686	0.687	0.686	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.096, 0.89	0.043, 0.085, 0.87	0.044, 0.086, 0.88	0.042, 0.081, 0.88
No. of reflections	2578	2570	2562	2558
No. of parameters	130	130	130	130
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.17	0.16, −0.18	0.16, −0.20	0.21, −0.18

	(200)	(175)	(150)	(125)
Crystal data
Chemical formula	C₅H₈O₄·C₂H₅NO₂	C₅H₈O₄·C₂H₅NO₂	C₅H₈O₄·C₂H₅NO₂	C₅H₈O₄·C₂H₅NO₂
M_r	207.18	207.18	207.18	207.18
Crystal system, space group	Triclinic, P1	Triclinic, P1	Triclinic, P1	Triclinic, P1
Temperature (K)	200	175	150	125
a, b, c (Å)	4.9155 (7), 20.215 (3), 10.1862 (16)	4.9098 (7), 20.194 (3), 10.1777 (15)	4.9021 (7), 20.167 (3), 10.1686 (15)	4.8952 (6), 20.151 (3), 10.1585 (13)
α, β, γ (°)	85.578 (14), 113.133 (11), 88.301 (13)	85.571 (13), 113.118 (10), 88.306 (12)	85.540 (11), 113.122 (10), 88.270 (11)	85.518 (11), 113.088 (9), 88.264 (11)
V (Å³)	926.1 (2)	923.3 (2)	919.7 (2)	916.9 (2)
Z	4	4	4	4
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.13	0.13	0.13	0.13
Crystal size (mm)	0.40 × 0.23 × 0.10	0.40 × 0.23 × 0.10	0.40 × 0.23 × 0.10	0.40 × 0.23 × 0.10

Data collection
Diffractometer	STOE IPDS 2 diffractometer	STOE IPDS 2 diffractometer	STOE IPDS 2 diffractometer	STOE IPDS 2 diffractometer
Absorption correction	–	–	–	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9663, 4312, 2491	9568, 4319, 2580	10066, 4417, 2840	9997, 4391, 2935
R_int	0.055	0.052	0.040	0.038
(sin θ/λ)_max (Å⁻¹)	0.686	0.687	0.686	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.081, 0.89	0.049, 0.088, 0.89	0.039, 0.077, 0.88	0.039, 0.075, 0.90
No. of reflections	4312	4319	4417	4391
No. of parameters	259	259	259	259
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.21	0.22, −0.23	0.21, −0.20	0.23, −0.20

	(100)
Crystal data
Chemical formula	C₅H₈O₄·C₂H₅NO₂
M_r	207.18
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	4.8884 (7), 20.136 (3), 10.1518 (15)
α, β, γ (°)	85.486 (13), 113.065 (10), 88.263 (12)
V (Å³)	914.5 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.40 × 0.23 × 0.10

Data collection
Diffractometer	STOE IPDS 2 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8816, 4247, 2766
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.097, 0.98
No. of reflections	4247
No. of parameters	259
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.29

Computer programs: STOE X-AREA (Stoe & Cie, 2006), STOE X-RED (Stoe & Cie, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and X-STEP32 (Stoe & Cie, 2000), Mercury (Macrae et al., 2006), PLATON (Spek, 2009), enCIFer (Allen et al., 2004).

Hydrogen-bond geometry (Å, º) for (300) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O3ⁱ	0.89	2.14	2.9671 (19)	154.2
N1—H1C···O3ⁱⁱ	0.89	2.00	2.8824 (19)	169.4
N1—H1A···O5	0.89	2.00	2.7665 (18)	143.2
O4—H4···O1ⁱⁱⁱ	0.82	1.75	2.5706 (18)	177.5
O6—H6···O2^iv	0.82	1.75	2.5444 (18)	164.4

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

Hydrogen-bond geometry (Å, º) for (275) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O3ⁱ	0.89	2.13	2.9564 (18)	154.2
N1—H1C···O3ⁱⁱ	0.89	2.00	2.8789 (18)	169.4
N1—H1A···O5	0.89	2.00	2.7658 (17)	143.2
O4—H4···O1ⁱⁱⁱ	0.82	1.75	2.5680 (17)	176.4
O6—H6···O2^iv	0.82	1.74	2.5425 (17)	164.5

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

Hydrogen-bond geometry (Å, º) for (250) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O3ⁱ	0.90	2.12	2.9504 (17)	153.4
N1—H1C···O3ⁱⁱ	0.90	1.99	2.8760 (18)	169.5
N1—H1A···O5	0.90	1.98	2.7621 (17)	143.8
O4—H4···O1ⁱⁱⁱ	0.83	1.74	2.5676 (16)	177.9
O6—H6···O2^iv	0.83	1.73	2.5414 (16)	164.6

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

Hydrogen-bond geometry (Å, º) for (225) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O3ⁱ	0.90	2.11	2.9420 (16)	154.0
N1—H1C···O3ⁱⁱ	0.90	1.98	2.8716 (16)	169.5
N1—H1A···O5	0.90	1.99	2.7641 (15)	143.2
O4—H4···O1ⁱⁱⁱ	0.83	1.74	2.5650 (15)	174.7
O6—H6···O2^iv	0.83	1.73	2.5417 (15)	164.9

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

Hydrogen-bond geometry (Å, º) for (200) top

D—H···A	D—H	H···A	D···A	D—H···A
O14—H14···O21ⁱ	0.84	1.74	2.580 (2)	176.1
O16—H16···O12ⁱⁱ	0.84	1.75	2.565 (2)	163.5
N11—H11A···O15	0.91	2.12	2.827 (2)	133.5
N11—H11B···O23ⁱⁱⁱ	0.91	1.96	2.860 (2)	168.1
N11—H11C···O23	0.91	2.11	2.971 (2)	158.0
O24—H24···O11^iv	0.84	1.72	2.5636 (18)	176.0
O26—H26···O22^v	0.84	1.73	2.555 (2)	167.3
N21—H21A···O25	0.91	2.05	2.798 (2)	138.5
N21—H21B···O13ⁱⁱ	0.91	1.96	2.861 (2)	172.2
N21—H21C···O13^vi	0.91	2.14	2.984 (2)	154.5

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

Hydrogen-bond geometry (Å, º) for (175) top

D—H···A	D—H	H···A	D···A	D—H···A
O14—H14···O21ⁱ	0.84	1.74	2.579 (2)	177.5
O16—H16···O12ⁱⁱ	0.84	1.74	2.567 (2)	165.9
N11—H11A···O15	0.91	2.12	2.826 (2)	133.2
N11—H11B···O23ⁱⁱⁱ	0.91	1.96	2.860 (2)	168.2
N11—H11C···O23	0.91	2.10	2.967 (2)	158.3
O24—H24···O11^iv	0.84	1.73	2.5655 (18)	176.3
O26—H26···O22^v	0.84	1.73	2.552 (2)	165.7
N21—H21A···O25	0.91	2.07	2.800 (2)	136.8
N21—H21B···O13ⁱⁱ	0.91	1.95	2.859 (2)	171.8
N21—H21C···O13^vi	0.91	2.12	2.974 (2)	156.1

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

Hydrogen-bond geometry (Å, º) for (150) top

D—H···A	D—H	H···A	D···A	D—H···A
O14—H14···O21ⁱ	0.84	1.74	2.5745 (16)	173.6
O16—H16···O12ⁱⁱ	0.84	1.74	2.5658 (17)	165.6
N11—H11A···O15	0.91	2.11	2.8238 (16)	134.5
N11—H11B···O23ⁱⁱⁱ	0.91	1.96	2.8554 (18)	169.3
N11—H11C···O23	0.91	2.10	2.9644 (17)	157.5
O24—H24···O11^iv	0.84	1.72	2.5626 (14)	175.5
O26—H26···O22^v	0.84	1.73	2.5550 (16)	166.1
N21—H21A···O25	0.91	2.07	2.7944 (17)	135.6
N21—H21B···O13ⁱⁱ	0.91	1.95	2.8551 (17)	171.1
N21—H21C···O13^vi	0.91	2.11	2.9719 (18)	157.0

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

Hydrogen-bond geometry (Å, º) for (125) top

D—H···A	D—H	H···A	D···A	D—H···A
O14—H14···O21ⁱ	0.84	1.74	2.5739 (16)	175.1
O16—H16···O12ⁱⁱ	0.84	1.74	2.5644 (16)	165.7
N11—H11A···O15	0.91	2.13	2.8245 (15)	132.5
N11—H11B···O23ⁱⁱⁱ	0.91	1.96	2.8537 (18)	168.4
N11—H11C···O23	0.91	2.09	2.9564 (17)	158.6
O24—H24···O11^iv	0.84	1.72	2.5623 (14)	176.1
O26—H26···O22^v	0.84	1.73	2.5539 (16)	167.0
N21—H21A···O25	0.91	2.06	2.7956 (17)	136.8
N21—H21B···O13ⁱⁱ	0.91	1.95	2.8522 (17)	172.2
N21—H21C···O13^vi	0.91	2.11	2.9639 (17)	156.0

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

Hydrogen-bond geometry (Å, º) for (100) top

D—H···A	D—H	H···A	D···A	D—H···A
O14—H14···O21ⁱ	0.84	1.73	2.571 (2)	177.3
O16—H16···O12ⁱⁱ	0.84	1.75	2.568 (2)	163.8
N11—H11A···O15	0.91	2.14	2.824 (2)	131.3
N11—H11B···O23ⁱⁱⁱ	0.91	1.96	2.851 (2)	167.5
N11—H11C···O23	0.91	2.08	2.953 (2)	159.5
O24—H24···O11^iv	0.84	1.72	2.5611 (19)	174.5
O26—H26···O22^v	0.84	1.73	2.555 (2)	167.8
N21—H21A···O25	0.91	2.08	2.793 (2)	134.6
N21—H21B···O13ⁱⁱ	0.91	1.95	2.849 (2)	171.4
N21—H21C···O13^vi	0.91	2.10	2.961 (2)	157.7

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

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