Supramolecular networks and Hirshfeld surfaces of oxydi­acetic acid and iminodi­acetic acid salts

Oxydi­acetic acid (Oda) and iminodi­acetic acid (Ida) have been combined with two di­amines, namely ethyl­enedi­amine (en) and o-phenyl­enedi­amine (o-phen), to give three molecular crystals of compositions [(Oda²⁻)(en²⁺)]·H₂O (Odaen), [(Ida⁻)(0.5en⁺)] (Idaen) and [(Oda⁻)(o-phen⁺)] (Odaophen). Single crystal X-ray structure determination of the three molecular salts revealed that the hydrogen bonding interactions form distinct supramolecular chains. In Odaen, water molecules and Oda²⁻ anions generate one-dimensional supramolecular chains where two chains overlap each other in zigzag form. In Odaophen, Oda⁻ anions generate a one-dimensional linear supramolecular chain. In Idaen, both intermolecular and intramolecular proton transfer occurs. Ida⁻ anions generate a one-dimensional zigzag chain. These one-dimensional supramolecular chains extend to form different two-dimensional supramolecular chains by the interaction of diaminium and monoaminium cations. Intermolecular close contacts are also examined using Hirshfeld analysis to reveal similarities and differences in the crystal structures.

Computing details

For all structures, data collection: APEX2 (Bruker, 2004); cell refinement: APEX2/SAINT (Bruker, 2004); data reduction: SAINT/XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altornare et al., 1993); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2014).

(Odaen)

Crystal data

C4H4O5·C2H10N2·H2O	F(000) = 456
Mr = 212.21	Dx = 1.416 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.1517 (4) Å	Cell parameters from 6884 reflections
b = 11.9600 (5) Å	θ = 2.8–32.5°
c = 8.9955 (4) Å	µ = 0.13 mm^−1
β = 114.322 (2)°	T = 293 K
V = 995.25 (7) Å^3	BLOCK, colourless
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection

Bruker axs kappa apex II CCD Diffractometer	1751 independent reflections
Radiation source: fine-focus sealed tube	1523 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
ω and φ scan	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan SADABS (Bruker, 2004)	h = −12→12
Tmin = 0.961, Tmax = 0.980	k = −14→14
14678 measured reflections	l = −10→10

Refinement

Refinement on F^2	3 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.096	w = 1/[σ^2(Fo^2) + (0.045P)^2 + 0.4717P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
1751 reflections	Δρmax = 0.36 e Å^−3
159 parameters	Δρmin = −0.32 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
O1	0.70624 (12)	0.11013 (10)	0.74876 (13)	0.0361 (3)
O2	0.90686 (13)	0.09199 (10)	1.04892 (13)	0.0397 (3)
O3	1.03928 (13)	0.22829 (11)	1.01514 (15)	0.0466 (4)
O5	0.48302 (13)	0.15399 (11)	0.32453 (13)	0.0426 (3)
O4	0.68919 (13)	0.06339 (11)	0.44199 (15)	0.0444 (3)
O6	0.74129 (16)	−0.22281 (14)	1.19017 (19)	0.0651 (5)
N1	0.66570 (15)	−0.04636 (12)	0.97259 (17)	0.0300 (3)
N2	0.91647 (15)	−0.07137 (12)	0.62676 (17)	0.0304 (3)
C5	0.56851 (17)	0.02961 (14)	1.0099 (2)	0.0322 (4)
H5A	0.5451	0.0936	0.9373	0.039*
H5B	0.6173	0.0566	1.1210	0.039*
C1	0.93002 (16)	0.16669 (13)	0.96682 (18)	0.0276 (3)
C6	1.02211 (17)	−0.00443 (14)	0.59094 (18)	0.0305 (4)
H6C	1.1167	−0.0391	0.6416	0.037*
H6D	1.0287	0.0699	0.6368	0.037*
C3	0.58231 (16)	0.14319 (14)	0.60976 (18)	0.0307 (4)
H3A	0.5687	0.2230	0.6163	0.037*
H3B	0.4985	0.1060	0.6127	0.037*
C2	0.81807 (17)	0.18991 (13)	0.79648 (18)	0.0319 (4)
H2A	0.7778	0.2639	0.7929	0.038*
H2B	0.8637	0.1885	0.7206	0.038*
C4	0.58826 (16)	0.11794 (13)	0.44745 (18)	0.0271 (3)
H1C	0.617 (2)	−0.0772 (16)	0.868 (3)	0.042 (5)*
H1A	0.744 (2)	−0.0047 (18)	0.973 (2)	0.046 (5)*
H2D	0.953 (2)	−0.0775 (16)	0.743 (3)	0.048 (5)*
H2E	0.825 (2)	−0.0362 (17)	0.584 (2)	0.045 (5)*
H1B	0.700 (2)	−0.1026 (18)	1.050 (3)	0.048 (5)*
H2C	0.908 (2)	−0.144 (2)	0.581 (3)	0.056 (6)*
H6A	0.813 (2)	−0.241 (2)	1.284 (2)	0.084 (8)*
H6B	0.660 (2)	−0.262 (2)	1.182 (3)	0.089 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0352 (6)	0.0354 (6)	0.0237 (6)	−0.0115 (5)	−0.0019 (5)	0.0068 (5)
O2	0.0368 (7)	0.0473 (7)	0.0254 (6)	−0.0096 (5)	0.0031 (5)	0.0089 (5)
O3	0.0383 (7)	0.0476 (7)	0.0377 (7)	−0.0167 (6)	−0.0008 (5)	0.0047 (6)
O5	0.0377 (7)	0.0541 (8)	0.0241 (6)	0.0185 (6)	0.0008 (5)	−0.0019 (5)
O4	0.0355 (7)	0.0578 (8)	0.0374 (7)	0.0192 (6)	0.0124 (5)	0.0027 (6)
O6	0.0406 (8)	0.0723 (10)	0.0584 (9)	−0.0172 (7)	−0.0038 (7)	0.0357 (8)
N1	0.0304 (7)	0.0330 (7)	0.0256 (7)	−0.0030 (6)	0.0104 (6)	0.0007 (6)
N2	0.0280 (7)	0.0331 (8)	0.0264 (7)	0.0021 (6)	0.0073 (6)	0.0046 (6)
C5	0.0346 (9)	0.0327 (8)	0.0302 (8)	−0.0047 (7)	0.0142 (7)	−0.0040 (6)
C1	0.0279 (8)	0.0281 (8)	0.0243 (8)	−0.0017 (6)	0.0081 (6)	−0.0017 (6)
C6	0.0262 (8)	0.0346 (8)	0.0261 (8)	0.0007 (6)	0.0061 (6)	0.0025 (6)
C3	0.0260 (8)	0.0367 (9)	0.0237 (8)	−0.0019 (6)	0.0044 (6)	0.0011 (6)
C2	0.0340 (9)	0.0300 (8)	0.0254 (8)	−0.0085 (7)	0.0060 (7)	0.0023 (6)
C4	0.0244 (8)	0.0262 (8)	0.0255 (8)	0.0003 (6)	0.0050 (6)	−0.0005 (6)

Geometric parameters (Å, º)

O1—C2	1.4079 (18)	N2—H2E	0.94 (2)
O1—C3	1.4166 (18)	N2—H2C	0.95 (2)
O2—C1	1.2418 (19)	C5—C5^i	1.505 (3)
O3—C1	1.2510 (19)	C5—H5A	0.9700
O5—C4	1.2557 (18)	C5—H5B	0.9700
O4—C4	1.2326 (19)	C1—C2	1.511 (2)
O6—H6A	0.880 (16)	C6—C6^ii	1.512 (3)
O6—H6B	0.921 (16)	C6—H6C	0.9700
N1—C5	1.478 (2)	C6—H6D	0.9700
N1—H1C	0.94 (2)	C3—C4	1.516 (2)
N1—H1A	0.93 (2)	C3—H3A	0.9700
N1—H1B	0.93 (2)	C3—H3B	0.9700
N2—C6	1.476 (2)	C2—H2A	0.9700
N2—H2D	0.96 (2)	C2—H2B	0.9700
C2—O1—C3	113.04 (12)	O3—C1—C2	115.67 (13)
H6A—O6—H6B	108.1 (19)	N2—C6—C6^ii	110.83 (16)
C5—N1—H1C	110.0 (12)	N2—C6—H6C	109.5
C5—N1—H1A	108.3 (12)	C6^ii—C6—H6C	109.5
H1C—N1—H1A	108.2 (16)	N2—C6—H6D	109.5
C5—N1—H1B	110.8 (13)	C6^ii—C6—H6D	109.5
H1C—N1—H1B	110.5 (17)	H6C—C6—H6D	108.1
H1A—N1—H1B	108.9 (18)	O1—C3—C4	114.91 (13)
C6—N2—H2D	106.7 (12)	O1—C3—H3A	108.5
C6—N2—H2E	110.5 (12)	C4—C3—H3A	108.5
H2D—N2—H2E	110.8 (17)	O1—C3—H3B	108.5
C6—N2—H2C	110.1 (13)	C4—C3—H3B	108.5
H2D—N2—H2C	109.4 (17)	H3A—C3—H3B	107.5
H2E—N2—H2C	109.4 (18)	O1—C2—C1	111.10 (12)
N1—C5—C5^i	110.78 (17)	O1—C2—H2A	109.4
N1—C5—H5A	109.5	C1—C2—H2A	109.4
C5^i—C5—H5A	109.5	O1—C2—H2B	109.4
N1—C5—H5B	109.5	C1—C2—H2B	109.4
C5^i—C5—H5B	109.5	H2A—C2—H2B	108.0
H5A—C5—H5B	108.1	O4—C4—O5	124.50 (15)
O2—C1—O3	125.10 (14)	O4—C4—C3	120.47 (13)
O2—C1—C2	119.20 (13)	O5—C4—C3	115.00 (13)
C2—O1—C3—C4	84.27 (17)	O3—C1—C2—O1	174.78 (14)
C3—O1—C2—C1	165.01 (13)	O1—C3—C4—O4	6.4 (2)
O2—C1—C2—O1	−7.0 (2)	O1—C3—C4—O5	−175.33 (14)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6C···O4^ii	0.97	2.40	3.145 (2)	133
N1—H1C···O5^iii	0.94 (2)	1.85 (2)	2.7849 (18)	172.5 (17)
N1—H1A···O1	0.93 (2)	2.34 (2)	2.8997 (18)	118.0 (15)
N1—H1A···O2	0.93 (2)	1.90 (2)	2.7961 (19)	159.9 (18)
N2—H2D···O2^iv	0.96 (2)	1.83 (2)	2.7347 (18)	155.8 (18)
N2—H2E···O4	0.94 (2)	1.87 (2)	2.7431 (18)	152.4 (17)
N1—H1B···O6	0.93 (2)	1.84 (2)	2.763 (2)	171.4 (19)
N2—H2C···O3^v	0.95 (2)	1.94 (2)	2.836 (2)	157.5 (19)
O6—H6A···O3^vi	0.88 (2)	1.85 (2)	2.7326 (18)	177 (3)
O6—H6B···O5^vii	0.92 (2)	1.75 (2)	2.6695 (18)	175 (2)

Symmetry codes: (ii) −x+2, −y, −z+1; (iii) −x+1, −y, −z+1; (iv) −x+2, −y, −z+2; (v) −x+2, y−1/2, −z+3/2; (vi) −x+2, y−1/2, −z+5/2; (vii) −x+1, y−1/2, −z+3/2.

(Odaophen)

Crystal data

C4H5O5·C6H9N2	F(000) = 1536
Mr = 242.23	Dx = 1.404 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.3828 (6) Å	Cell parameters from 9910 reflections
b = 23.9943 (17) Å	θ = 2.0–26.1°
c = 17.2844 (10) Å	µ = 0.11 mm^−1
β = 98.635 (3)°	T = 296 K
V = 3437.2 (4) Å^3	Block, brown
Z = 12	0.25 × 0.25 × 0.20 mm

Data collection

Bruker axs kappa apex II CCD Diffractometer	7322 independent reflections
Radiation source: fine-focus sealed tube	4455 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
ω and φ scan	θmax = 26.8°, θmin = 2.1°
Absorption correction: multi-scan SADABS (Bruker, 2004)	h = −10→10
Tmin = 0.964, Tmax = 0.979	k = −30→30
53011 measured reflections	l = −19→21

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.131	w = 1/[σ^2(Fo^2) + (0.055P)^2 + 1.2016P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
7322 reflections	Δρmax = 0.25 e Å^−3
520 parameters	Δρmin = −0.25 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
C1	0.7794 (2)	−0.09869 (9)	0.91838 (11)	0.0333 (5)
C2	0.6889 (3)	−0.13676 (9)	0.87110 (12)	0.0414 (5)
C3	0.6685 (3)	−0.18916 (11)	0.90194 (15)	0.0581 (7)
H3	0.6105	−0.2161	0.8708	0.070*
C4	0.7321 (4)	−0.20182 (11)	0.97715 (15)	0.0664 (8)
H4	0.7152	−0.2370	0.9970	0.080*
C5	0.8203 (3)	−0.16342 (11)	1.02352 (14)	0.0618 (7)
H5	0.8632	−0.1723	1.0748	0.074*
C6	0.8454 (3)	−0.11162 (10)	0.99380 (12)	0.0452 (6)
H6	0.9069	−0.0854	1.0247	0.054*
C7	0.0170 (2)	0.20620 (9)	0.78078 (11)	0.0340 (5)
C8	0.0792 (2)	0.15617 (8)	0.75874 (10)	0.0302 (4)
C9	0.0145 (3)	0.10586 (9)	0.77538 (12)	0.0403 (5)
H9	0.0596	0.0729	0.7605	0.048*
C10	−0.1173 (3)	0.10436 (11)	0.81410 (13)	0.0520 (6)
H10	−0.1621	0.0704	0.8254	0.062*
C11	−0.1820 (3)	0.15344 (12)	0.83587 (14)	0.0536 (7)
H11	−0.2711	0.1526	0.8621	0.064*
C12	−0.1168 (3)	0.20351 (11)	0.81938 (12)	0.0468 (6)
H12	−0.1628	0.2363	0.8343	0.056*
C13	0.1373 (3)	0.36304 (9)	0.95104 (12)	0.0384 (5)
C14	0.2912 (2)	0.36263 (8)	0.99270 (11)	0.0326 (5)
C15	0.3168 (3)	0.35604 (10)	1.07267 (12)	0.0445 (6)
H15	0.4216	0.3559	1.0996	0.053*
C16	0.1888 (3)	0.34966 (11)	1.11315 (14)	0.0583 (7)
H16	0.2061	0.3453	1.1672	0.070*
C17	0.0360 (3)	0.34989 (12)	1.07278 (15)	0.0601 (7)
H17	−0.0514	0.3458	1.0996	0.072*
C18	0.0101 (3)	0.35615 (10)	0.99328 (14)	0.0526 (6)
H18	−0.0950	0.3558	0.9669	0.063*
C19	0.7247 (3)	0.05334 (9)	1.04556 (11)	0.0339 (5)
C20	0.5827 (3)	0.07208 (10)	0.98886 (11)	0.0397 (5)
H20A	0.4840	0.0638	1.0095	0.048*
H20B	0.5882	0.1121	0.9813	0.048*
C21	0.4544 (3)	0.06257 (9)	0.85952 (11)	0.0367 (5)
H21A	0.4619	0.1025	0.8523	0.044*
H21B	0.3519	0.0546	0.8768	0.044*
C22	0.4620 (3)	0.03334 (9)	0.78307 (11)	0.0351 (5)
C23	0.9765 (3)	0.05155 (9)	1.28236 (11)	0.0377 (5)
C24	1.1165 (3)	0.02541 (11)	1.33248 (12)	0.0565 (7)
H24A	1.1037	−0.0148	1.3314	0.068*
H24B	1.2148	0.0343	1.3118	0.068*
C25	1.2457 (3)	0.01539 (10)	1.46126 (12)	0.0480 (6)
H25A	1.3512	0.0208	1.4458	0.058*
H25B	1.2214	−0.0241	1.4587	0.058*
C26	1.2476 (3)	0.03571 (9)	1.54288 (11)	0.0378 (5)
C27	0.5008 (3)	0.25483 (10)	0.82390 (11)	0.0365 (5)
C28	0.4868 (3)	0.28736 (10)	0.74859 (12)	0.0461 (6)
H28A	0.4454	0.3243	0.7564	0.055*
H28B	0.5925	0.2913	0.7328	0.055*
C29	0.3576 (3)	0.28778 (10)	0.61760 (11)	0.0474 (6)
H29A	0.4590	0.2910	0.5974	0.057*
H29B	0.3177	0.3250	0.6250	0.057*
C30	0.2387 (3)	0.25681 (9)	0.56061 (11)	0.0359 (5)
N1	0.8052 (2)	−0.04269 (8)	0.88922 (11)	0.0351 (4)
N2	0.6257 (3)	−0.12480 (12)	0.79395 (12)	0.0650 (7)
N3	0.0815 (3)	0.25746 (8)	0.76503 (12)	0.0433 (5)
N4	0.2230 (2)	0.15661 (8)	0.72050 (10)	0.0328 (4)
N5	0.1065 (3)	0.36780 (10)	0.86980 (11)	0.0501 (5)
N6	0.4324 (2)	0.36917 (9)	0.95375 (11)	0.0369 (4)
O1	0.72007 (19)	0.07290 (7)	1.11550 (8)	0.0491 (4)
H1	0.7991	0.0619	1.1453	0.074*
O2	0.83091 (19)	0.02399 (7)	1.02860 (8)	0.0487 (4)
O3	0.58187 (17)	0.04469 (6)	0.91704 (7)	0.0402 (4)
O4	0.56051 (19)	−0.00396 (7)	0.77854 (8)	0.0478 (4)
O5	0.36074 (19)	0.05060 (6)	0.72649 (8)	0.0462 (4)
O6	0.8812 (2)	0.08095 (7)	1.31061 (8)	0.0551 (5)
O7	0.96370 (19)	0.04021 (7)	1.20988 (8)	0.0488 (4)
O8	1.1298 (2)	0.04434 (7)	1.41017 (8)	0.0499 (4)
O9	1.16385 (19)	0.07332 (7)	1.56054 (8)	0.0478 (4)
O10	1.3517 (2)	0.00892 (7)	1.59209 (8)	0.0551 (5)
H10A	1.3502	0.0210	1.6363	0.083*
O11	0.5746 (2)	0.27998 (7)	0.88315 (8)	0.0500 (4)
O12	0.44613 (19)	0.20754 (7)	0.82468 (8)	0.0485 (4)
O13	0.38198 (18)	0.25944 (6)	0.68934 (7)	0.0393 (4)
O14	0.2161 (2)	0.28113 (7)	0.49259 (8)	0.0582 (5)
H14	0.1504	0.2633	0.4624	0.087*
O15	0.17223 (18)	0.21426 (6)	0.57534 (8)	0.0426 (4)
H1A	0.888 (3)	−0.0426 (10)	0.8555 (14)	0.054 (7)*
H1B	0.706 (3)	−0.0283 (11)	0.8577 (16)	0.070 (8)*
H1C	0.834 (3)	−0.0205 (11)	0.9307 (16)	0.066 (8)*
H2A	0.556 (4)	−0.1508 (13)	0.7764 (19)	0.089 (11)*
H2B	0.583 (4)	−0.0905 (14)	0.7877 (18)	0.087 (11)*
H3A	0.181 (3)	0.2573 (11)	0.7454 (15)	0.063 (8)*
H3B	0.079 (3)	0.2814 (11)	0.8023 (15)	0.060 (8)*
H4A	0.258 (3)	0.1193 (10)	0.7143 (12)	0.043 (6)*
H4B	0.203 (3)	0.1737 (10)	0.6709 (15)	0.054 (7)*
H4C	0.309 (3)	0.1765 (10)	0.7530 (14)	0.055 (7)*
H5A	0.181 (4)	0.3855 (12)	0.8455 (16)	0.074 (9)*
H5B	0.002 (4)	0.3767 (13)	0.8537 (18)	0.086 (10)*
H6A	0.514 (3)	0.3851 (10)	0.9861 (14)	0.048 (7)*
H6B	0.470 (3)	0.3348 (13)	0.9365 (16)	0.080 (9)*
H6C	0.408 (3)	0.3929 (12)	0.9063 (17)	0.076 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0349 (11)	0.0363 (12)	0.0280 (10)	0.0060 (9)	0.0030 (8)	−0.0006 (9)
C2	0.0466 (13)	0.0449 (14)	0.0299 (11)	0.0008 (11)	−0.0036 (9)	−0.0034 (10)
C3	0.0714 (18)	0.0470 (15)	0.0511 (15)	−0.0150 (13)	−0.0064 (13)	0.0004 (12)
C4	0.089 (2)	0.0491 (16)	0.0571 (17)	−0.0111 (15)	−0.0018 (15)	0.0148 (13)
C5	0.083 (2)	0.0590 (17)	0.0374 (13)	0.0000 (15)	−0.0112 (13)	0.0138 (12)
C6	0.0515 (14)	0.0470 (14)	0.0328 (11)	0.0018 (11)	−0.0075 (10)	0.0009 (10)
C7	0.0339 (11)	0.0417 (13)	0.0245 (10)	0.0061 (10)	−0.0017 (8)	0.0019 (9)
C8	0.0297 (11)	0.0379 (12)	0.0223 (9)	0.0024 (9)	0.0013 (8)	0.0026 (8)
C9	0.0420 (13)	0.0403 (13)	0.0374 (11)	−0.0022 (10)	0.0023 (10)	0.0013 (10)
C10	0.0488 (15)	0.0587 (17)	0.0483 (14)	−0.0120 (13)	0.0073 (11)	0.0070 (12)
C11	0.0388 (14)	0.080 (2)	0.0452 (13)	−0.0005 (13)	0.0156 (11)	0.0036 (13)
C12	0.0415 (14)	0.0606 (16)	0.0387 (12)	0.0120 (12)	0.0066 (10)	−0.0026 (11)
C13	0.0426 (13)	0.0359 (12)	0.0345 (11)	−0.0003 (10)	−0.0017 (10)	−0.0038 (9)
C14	0.0368 (12)	0.0313 (11)	0.0294 (10)	−0.0033 (9)	0.0043 (9)	0.0001 (8)
C15	0.0445 (14)	0.0549 (15)	0.0325 (11)	−0.0021 (11)	0.0007 (10)	0.0060 (10)
C16	0.0630 (18)	0.0774 (19)	0.0361 (13)	−0.0065 (14)	0.0124 (12)	0.0078 (12)
C17	0.0503 (16)	0.079 (2)	0.0547 (16)	−0.0087 (14)	0.0201 (13)	−0.0014 (13)
C18	0.0379 (14)	0.0641 (17)	0.0553 (15)	−0.0018 (12)	0.0048 (11)	−0.0038 (12)
C19	0.0414 (12)	0.0354 (12)	0.0246 (10)	−0.0005 (10)	0.0041 (9)	−0.0034 (9)
C20	0.0449 (13)	0.0478 (14)	0.0255 (10)	0.0097 (10)	0.0022 (9)	−0.0063 (9)
C21	0.0412 (13)	0.0411 (13)	0.0265 (10)	0.0090 (10)	0.0002 (9)	0.0023 (9)
C22	0.0405 (12)	0.0367 (12)	0.0267 (10)	0.0036 (10)	0.0008 (9)	0.0029 (9)
C23	0.0486 (13)	0.0419 (12)	0.0226 (10)	0.0004 (11)	0.0052 (9)	−0.0017 (9)
C24	0.0720 (18)	0.0677 (17)	0.0260 (11)	0.0234 (14)	−0.0048 (11)	−0.0110 (11)
C25	0.0639 (16)	0.0473 (14)	0.0290 (11)	0.0199 (12)	−0.0057 (10)	−0.0052 (10)
C26	0.0470 (13)	0.0375 (12)	0.0266 (10)	0.0074 (11)	−0.0018 (9)	0.0014 (9)
C27	0.0355 (12)	0.0455 (14)	0.0268 (11)	0.0077 (10)	−0.0010 (9)	−0.0031 (9)
C28	0.0579 (15)	0.0468 (14)	0.0293 (11)	−0.0099 (11)	−0.0078 (10)	−0.0014 (10)
C29	0.0649 (16)	0.0467 (14)	0.0269 (11)	−0.0133 (12)	−0.0051 (10)	0.0081 (10)
C30	0.0418 (12)	0.0411 (13)	0.0244 (10)	−0.0005 (10)	0.0033 (9)	0.0040 (9)
N1	0.0403 (11)	0.0375 (11)	0.0267 (9)	0.0047 (9)	0.0023 (8)	−0.0025 (8)
N2	0.099 (2)	0.0516 (15)	0.0350 (11)	−0.0072 (15)	−0.0223 (11)	−0.0047 (10)
N3	0.0485 (13)	0.0371 (12)	0.0440 (11)	0.0058 (9)	0.0056 (10)	−0.0008 (9)
N4	0.0366 (11)	0.0327 (10)	0.0291 (9)	0.0033 (8)	0.0055 (8)	0.0016 (8)
N5	0.0467 (13)	0.0655 (15)	0.0343 (11)	−0.0025 (12)	−0.0060 (10)	−0.0037 (10)
N6	0.0401 (11)	0.0410 (12)	0.0293 (9)	−0.0064 (9)	0.0042 (8)	−0.0007 (9)
O1	0.0551 (10)	0.0637 (11)	0.0257 (7)	0.0142 (8)	−0.0028 (7)	−0.0100 (7)
O2	0.0503 (10)	0.0603 (11)	0.0325 (8)	0.0157 (8)	−0.0036 (7)	−0.0115 (7)
O3	0.0467 (9)	0.0498 (9)	0.0211 (7)	0.0141 (7)	−0.0043 (6)	−0.0040 (6)
O4	0.0565 (10)	0.0527 (10)	0.0312 (8)	0.0226 (8)	−0.0032 (7)	−0.0027 (7)
O5	0.0577 (10)	0.0502 (10)	0.0264 (7)	0.0201 (8)	−0.0077 (7)	−0.0024 (7)
O6	0.0592 (11)	0.0742 (12)	0.0300 (8)	0.0202 (9)	0.0009 (7)	−0.0123 (8)
O7	0.0529 (10)	0.0703 (11)	0.0219 (7)	0.0096 (8)	0.0013 (6)	−0.0050 (7)
O8	0.0685 (11)	0.0550 (10)	0.0219 (7)	0.0241 (8)	−0.0077 (7)	−0.0063 (7)
O9	0.0579 (10)	0.0535 (10)	0.0295 (8)	0.0220 (8)	−0.0015 (7)	−0.0036 (7)
O10	0.0762 (12)	0.0572 (11)	0.0272 (8)	0.0312 (9)	−0.0076 (7)	−0.0046 (7)
O11	0.0624 (11)	0.0552 (10)	0.0274 (8)	0.0079 (8)	−0.0102 (7)	−0.0077 (7)
O12	0.0551 (10)	0.0520 (10)	0.0342 (8)	−0.0045 (8)	−0.0069 (7)	0.0081 (7)
O13	0.0511 (9)	0.0431 (9)	0.0205 (7)	−0.0096 (7)	−0.0049 (6)	0.0029 (6)
O14	0.0809 (12)	0.0603 (11)	0.0268 (8)	−0.0238 (9)	−0.0134 (8)	0.0140 (7)
O15	0.0474 (9)	0.0486 (10)	0.0297 (8)	−0.0076 (8)	−0.0014 (7)	0.0064 (7)

Geometric parameters (Å, º)

C1—C6	1.373 (3)	C21—H21B	0.9700
C1—C2	1.375 (3)	C22—O4	1.229 (2)
C1—N1	1.463 (3)	C22—O5	1.264 (2)
C2—C3	1.386 (3)	C23—O6	1.221 (2)
C2—N2	1.389 (3)	C23—O7	1.271 (2)
C3—C4	1.363 (3)	C23—C24	1.489 (3)
C3—H3	0.9300	C24—O8	1.406 (2)
C4—C5	1.364 (4)	C24—H24A	0.9700
C4—H4	0.9300	C24—H24B	0.9700
C5—C6	1.373 (3)	C25—O8	1.396 (3)
C5—H5	0.9300	C25—C26	1.490 (3)
C6—H6	0.9300	C25—H25A	0.9700
C7—C8	1.385 (3)	C25—H25B	0.9700
C7—N3	1.387 (3)	C26—O9	1.210 (2)
C7—C12	1.390 (3)	C26—O10	1.294 (2)
C8—C9	1.371 (3)	C27—O12	1.225 (3)
C8—N4	1.459 (3)	C27—O11	1.267 (2)
C9—C10	1.375 (3)	C27—C28	1.507 (3)
C9—H9	0.9300	C28—O13	1.414 (2)
C10—C11	1.373 (4)	C28—H28A	0.9700
C10—H10	0.9300	C28—H28B	0.9700
C11—C12	1.367 (3)	C29—O13	1.402 (2)
C11—H11	0.9300	C29—C30	1.490 (3)
C12—H12	0.9300	C29—H29A	0.9700
C13—C14	1.380 (3)	C29—H29B	0.9700
C13—C18	1.389 (3)	C30—O15	1.208 (2)
C13—N5	1.394 (3)	C30—O14	1.301 (2)
C14—C15	1.376 (3)	N1—H1A	0.97 (3)
C14—N6	1.455 (3)	N1—H1B	0.99 (3)
C15—C16	1.375 (3)	N1—H1C	0.90 (3)
C15—H15	0.9300	N2—H2A	0.88 (3)
C16—C17	1.363 (4)	N2—H2B	0.90 (3)
C16—H16	0.9300	N3—H3A	0.94 (3)
C17—C18	1.367 (3)	N3—H3B	0.87 (3)
C17—H17	0.9300	N4—H4A	0.95 (2)
C18—H18	0.9300	N4—H4B	0.94 (2)
C19—O2	1.205 (2)	N4—H4C	0.97 (3)
C19—O1	1.303 (2)	N5—H5A	0.91 (3)
C19—C20	1.493 (3)	N5—H5B	0.90 (3)
C20—O3	1.404 (2)	N6—H6A	0.90 (3)
C20—H20A	0.9700	N6—H6B	0.95 (3)
C20—H20B	0.9700	N6—H6C	0.99 (3)
C21—O3	1.412 (2)	O1—H1	0.8200
C21—C22	1.506 (3)	O10—H10A	0.8200
C21—H21A	0.9700	O14—H14	0.8200
C6—C1—C2	121.5 (2)	O5—C22—C21	114.49 (18)
C6—C1—N1	118.38 (19)	O6—C23—O7	123.7 (2)
C2—C1—N1	120.16 (18)	O6—C23—C24	121.11 (18)
C1—C2—C3	117.6 (2)	O7—C23—C24	115.19 (19)
C1—C2—N2	122.0 (2)	O8—C24—C23	111.21 (19)
C3—C2—N2	120.4 (2)	O8—C24—H24A	109.4
C4—C3—C2	121.0 (2)	C23—C24—H24A	109.4
C4—C3—H3	119.5	O8—C24—H24B	109.4
C2—C3—H3	119.5	C23—C24—H24B	109.4
C3—C4—C5	120.6 (2)	H24A—C24—H24B	108.0
C3—C4—H4	119.7	O8—C25—C26	110.10 (18)
C5—C4—H4	119.7	O8—C25—H25A	109.6
C4—C5—C6	119.4 (2)	C26—C25—H25A	109.6
C4—C5—H5	120.3	O8—C25—H25B	109.6
C6—C5—H5	120.3	C26—C25—H25B	109.6
C5—C6—C1	119.8 (2)	H25A—C25—H25B	108.2
C5—C6—H6	120.1	O9—C26—O10	124.34 (19)
C1—C6—H6	120.1	O9—C26—C25	123.94 (18)
C8—C7—N3	122.76 (19)	O10—C26—C25	111.71 (19)
C8—C7—C12	117.1 (2)	O12—C27—O11	124.79 (19)
N3—C7—C12	120.1 (2)	O12—C27—C28	120.58 (18)
C9—C8—C7	121.90 (19)	O11—C27—C28	114.6 (2)
C9—C8—N4	118.76 (18)	O13—C28—C27	109.84 (18)
C7—C8—N4	119.26 (18)	O13—C28—H28A	109.7
C8—C9—C10	119.8 (2)	C27—C28—H28A	109.7
C8—C9—H9	120.1	O13—C28—H28B	109.7
C10—C9—H9	120.1	C27—C28—H28B	109.7
C11—C10—C9	119.4 (2)	H28A—C28—H28B	108.2
C11—C10—H10	120.3	O13—C29—C30	109.71 (18)
C9—C10—H10	120.3	O13—C29—H29A	109.7
C12—C11—C10	120.6 (2)	C30—C29—H29A	109.7
C12—C11—H11	119.7	O13—C29—H29B	109.7
C10—C11—H11	119.7	C30—C29—H29B	109.7
C11—C12—C7	121.2 (2)	H29A—C29—H29B	108.2
C11—C12—H12	119.4	O15—C30—O14	124.06 (19)
C7—C12—H12	119.4	O15—C30—C29	124.46 (18)
C14—C13—C18	117.13 (19)	O14—C30—C29	111.48 (19)
C14—C13—N5	122.9 (2)	C1—N1—H1A	111.3 (14)
C18—C13—N5	119.9 (2)	C1—N1—H1B	110.8 (15)
C15—C14—C13	121.2 (2)	H1A—N1—H1B	107 (2)
C15—C14—N6	117.54 (19)	C1—N1—H1C	107.8 (17)
C13—C14—N6	121.29 (18)	H1A—N1—H1C	110 (2)
C16—C15—C14	120.6 (2)	H1B—N1—H1C	110 (2)
C16—C15—H15	119.7	C2—N2—H2A	109 (2)
C14—C15—H15	119.7	C2—N2—H2B	113 (2)
C17—C16—C15	119.0 (2)	H2A—N2—H2B	112 (3)
C17—C16—H16	120.5	C7—N3—H3A	117.2 (16)
C15—C16—H16	120.5	C7—N3—H3B	113.0 (17)
C16—C17—C18	120.7 (2)	H3A—N3—H3B	113 (2)
C16—C17—H17	119.7	C8—N4—H4A	109.6 (13)
C18—C17—H17	119.7	C8—N4—H4B	111.8 (14)
C17—C18—C13	121.5 (2)	H4A—N4—H4B	108.7 (19)
C17—C18—H18	119.2	C8—N4—H4C	109.6 (14)
C13—C18—H18	119.2	H4A—N4—H4C	108.0 (19)
O2—C19—O1	124.21 (19)	H4B—N4—H4C	109 (2)
O2—C19—C20	124.15 (18)	C13—N5—H5A	117.9 (18)
O1—C19—C20	111.64 (18)	C13—N5—H5B	110.7 (19)
O3—C20—C19	109.72 (17)	H5A—N5—H5B	117 (3)
O3—C20—H20A	109.7	C14—N6—H6A	110.8 (14)
C19—C20—H20A	109.7	C14—N6—H6B	112.8 (17)
O3—C20—H20B	109.7	H6A—N6—H6B	108 (2)
C19—C20—H20B	109.7	C14—N6—H6C	111.1 (15)
H20A—C20—H20B	108.2	H6A—N6—H6C	108 (2)
O3—C21—C22	110.45 (16)	H6B—N6—H6C	106 (2)
O3—C21—H21A	109.6	C19—O1—H1	109.5
C22—C21—H21A	109.6	C20—O3—C21	112.53 (15)
O3—C21—H21B	109.6	C25—O8—C24	113.03 (17)
C22—C21—H21B	109.6	C26—O10—H10A	109.5
H21A—C21—H21B	108.1	C29—O13—C28	113.78 (16)
O4—C22—O5	124.67 (18)	C30—O14—H14	109.5
O4—C22—C21	120.83 (17)
C6—C1—C2—C3	−0.9 (3)	C13—C14—C15—C16	0.0 (3)
N1—C1—C2—C3	−180.0 (2)	N6—C14—C15—C16	180.0 (2)
C6—C1—C2—N2	−177.9 (2)	C14—C15—C16—C17	0.1 (4)
N1—C1—C2—N2	3.0 (3)	C15—C16—C17—C18	0.2 (4)
C1—C2—C3—C4	1.8 (4)	C16—C17—C18—C13	−0.7 (4)
N2—C2—C3—C4	178.9 (3)	C14—C13—C18—C17	0.8 (4)
C2—C3—C4—C5	−1.3 (5)	N5—C13—C18—C17	178.3 (2)
C3—C4—C5—C6	−0.2 (5)	O2—C19—C20—O3	7.6 (3)
C4—C5—C6—C1	1.1 (4)	O1—C19—C20—O3	−172.71 (17)
C2—C1—C6—C5	−0.5 (3)	O3—C21—C22—O4	5.9 (3)
N1—C1—C6—C5	178.6 (2)	O3—C21—C22—O5	−173.96 (18)
N3—C7—C8—C9	179.50 (19)	O6—C23—C24—O8	−6.6 (4)
C12—C7—C8—C9	−1.3 (3)	O7—C23—C24—O8	174.4 (2)
N3—C7—C8—N4	2.9 (3)	O8—C25—C26—O9	−2.5 (3)
C12—C7—C8—N4	−177.88 (18)	O8—C25—C26—O10	178.7 (2)
C7—C8—C9—C10	0.9 (3)	O12—C27—C28—O13	10.4 (3)
N4—C8—C9—C10	177.51 (19)	O11—C27—C28—O13	−170.95 (18)
C8—C9—C10—C11	−0.3 (3)	O13—C29—C30—O15	1.2 (3)
C9—C10—C11—C12	0.0 (4)	O13—C29—C30—O14	−178.33 (19)
C10—C11—C12—C7	−0.5 (4)	C19—C20—O3—C21	−177.18 (17)
C8—C7—C12—C11	1.1 (3)	C22—C21—O3—C20	178.21 (18)
N3—C7—C12—C11	−179.7 (2)	C26—C25—O8—C24	−177.3 (2)
C18—C13—C14—C15	−0.4 (3)	C23—C24—O8—C25	171.8 (2)
N5—C13—C14—C15	−177.9 (2)	C30—C29—O13—C28	−176.81 (19)
C18—C13—C14—N6	179.6 (2)	C27—C28—O13—C29	178.01 (19)
N5—C13—C14—N6	2.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21A···O12	0.97	2.56	3.529 (3)	173
C28—H28A···O6^i	0.97	2.55	3.493 (3)	165
C29—H29B···O1^i	0.97	2.58	3.535 (3)	168
O1—H1···O7	0.82	1.72	2.539 (2)	178
O10—H10A···O5^ii	0.82	1.70	2.520 (2)	175
O14—H14···O11^i	0.82	1.76	2.542 (2)	159
N1—H1A···O7^iii	0.97 (3)	1.80 (3)	2.772 (2)	177 (2)
N1—H1B···O3	0.99 (3)	2.35 (3)	2.899 (2)	114.3 (19)
N1—H1B···O4	0.99 (3)	1.79 (3)	2.748 (2)	164 (2)
N1—H1C···O2	0.90 (3)	2.00 (3)	2.873 (2)	163 (2)
N2—H2A···N3^iv	0.88 (3)	2.54 (3)	3.392 (3)	165 (3)
N2—H2B···O4	0.90 (3)	2.09 (3)	2.955 (3)	162 (3)
N3—H3A···O13	0.94 (3)	2.07 (3)	3.008 (3)	173 (2)
N3—H3B···N5	0.87 (3)	2.37 (3)	3.197 (3)	159 (2)
N4—H4A···O5	0.95 (2)	1.86 (2)	2.789 (2)	165.2 (19)
N4—H4B···O15	0.94 (2)	1.90 (3)	2.841 (2)	175 (2)
N4—H4C···O12	0.97 (3)	1.73 (3)	2.688 (2)	170 (2)
N4—H4C···O13	0.97 (3)	2.40 (2)	2.893 (2)	111.2 (17)
N5—H5A···O6^i	0.91 (3)	2.03 (3)	2.927 (3)	168 (3)
N5—H5B···N2^v	0.90 (3)	2.62 (3)	3.190 (3)	122 (2)
N6—H6A···O9^i	0.90 (3)	1.93 (3)	2.828 (2)	171 (2)
N6—H6B···O11	0.95 (3)	1.89 (3)	2.815 (3)	164 (3)
N6—H6C···O6^i	0.99 (3)	1.75 (3)	2.724 (2)	165 (2)

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

(Idaen)

Crystal data

C4H6NO4·0.5(C2H10N2)	F(000) = 348
Mr = 163.16	Dx = 1.523 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.1027 (2) Å	Cell parameters from 5165 reflections
b = 16.0240 (7) Å	θ = 2.5–37.8°
c = 8.7273 (4) Å	µ = 0.13 mm^−1
β = 94.459 (2)°	T = 293 K
V = 711.43 (5) Å^3	BLOCK, colourless
Z = 4	0.35 × 0.25 × 0.20 mm

Data collection

Bruker axs kappa apex II CCD Diffractometer	1249 independent reflections
Radiation source: fine-focus sealed tube	1143 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
ω and φ scan	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan SADABS (Bruker, 2004)	h = −6→6
Tmin = 0.951, Tmax = 0.980	k = −19→19
7700 measured reflections	l = −10→10

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.032	w = 1/[σ^2(Fo^2) + (0.0353P)^2 + 0.3566P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.081	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.30 e Å^−3
1249 reflections	Δρmin = −0.18 e Å^−3
121 parameters	Extinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.011 (4)

Special details

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

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

	x	y	z	Uiso*/Ueq
C1	−0.0078 (3)	0.29413 (8)	0.92881 (16)	0.0208 (3)
C2	0.1246 (3)	0.24723 (9)	1.06511 (16)	0.0228 (3)
H2A	0.1658	0.2863	1.1484	0.027*
H2B	0.0024	0.2064	1.1004	0.027*
C3	0.3305 (3)	0.13564 (9)	0.91421 (17)	0.0270 (4)
H3A	0.2714	0.1591	0.8150	0.032*
H3B	0.1955	0.0979	0.9450	0.032*
C4	0.5844 (3)	0.08741 (9)	0.90038 (16)	0.0233 (3)
C5	0.1087 (3)	−0.00714 (10)	0.56171 (16)	0.0270 (4)
H5A	0.2414	−0.0431	0.5230	0.032*
H5B	0.1908	0.0457	0.5913	0.032*
N1	0.3696 (2)	0.20387 (7)	1.02893 (14)	0.0198 (3)
N2	0.0014 (3)	−0.04631 (8)	0.69674 (15)	0.0249 (3)
O1	−0.2451 (2)	0.31245 (6)	0.93836 (13)	0.0317 (3)
O2	0.1266 (2)	0.31209 (7)	0.82090 (12)	0.0298 (3)
O3	0.6081 (3)	0.05500 (9)	0.77295 (14)	0.0521 (4)
O4	0.7436 (2)	0.08419 (7)	1.01368 (12)	0.0347 (3)
H1B	0.449 (3)	0.1834 (11)	1.120 (2)	0.031 (4)*
H1A	0.482 (4)	0.2408 (11)	0.994 (2)	0.029 (4)*
H2E	0.130 (4)	−0.0544 (11)	0.772 (2)	0.036 (5)*
H2C	−0.130 (4)	−0.0132 (13)	0.736 (2)	0.043 (5)*
H2D	−0.076 (4)	−0.0954 (14)	0.666 (2)	0.044 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0201 (7)	0.0164 (7)	0.0254 (7)	−0.0024 (5)	−0.0012 (6)	−0.0011 (5)
C2	0.0217 (7)	0.0266 (7)	0.0207 (7)	0.0044 (6)	0.0044 (6)	0.0004 (6)
C3	0.0220 (8)	0.0299 (8)	0.0283 (8)	0.0021 (6)	−0.0022 (6)	−0.0087 (6)
C4	0.0231 (8)	0.0225 (7)	0.0243 (7)	0.0014 (6)	0.0021 (6)	−0.0005 (6)
C5	0.0237 (8)	0.0309 (8)	0.0259 (8)	−0.0017 (6)	−0.0021 (6)	0.0036 (6)
N1	0.0175 (6)	0.0219 (6)	0.0199 (6)	0.0013 (5)	0.0006 (5)	0.0005 (5)
N2	0.0292 (7)	0.0238 (7)	0.0212 (6)	0.0033 (6)	−0.0017 (5)	0.0003 (5)
O1	0.0211 (6)	0.0275 (6)	0.0466 (7)	0.0049 (4)	0.0028 (5)	0.0088 (5)
O2	0.0263 (6)	0.0383 (6)	0.0246 (6)	−0.0029 (5)	0.0002 (4)	0.0090 (5)
O3	0.0493 (8)	0.0726 (10)	0.0330 (7)	0.0311 (7)	−0.0053 (6)	−0.0217 (6)
O4	0.0300 (6)	0.0416 (7)	0.0311 (6)	0.0099 (5)	−0.0070 (5)	−0.0034 (5)

Geometric parameters (Å, º)

C1—O2	1.2410 (17)	C4—O3	1.2417 (19)
C1—O1	1.2550 (18)	C5—N2	1.4774 (19)
C1—C2	1.5202 (19)	C5—C5^i	1.502 (3)
C2—N1	1.4856 (17)	C5—H5A	0.9700
C2—H2A	0.9700	C5—H5B	0.9700
C2—H2B	0.9700	N1—H1B	0.927 (19)
C3—N1	1.4854 (18)	N1—H1A	0.895 (19)
C3—C4	1.522 (2)	N2—H2E	0.90 (2)
C3—H3A	0.9700	N2—H2C	0.94 (2)
C3—H3B	0.9700	N2—H2D	0.91 (2)
C4—O4	1.2307 (18)
O2—C1—O1	126.09 (13)	N2—C5—C5^i	109.74 (15)
O2—C1—C2	118.05 (12)	N2—C5—H5A	109.7
O1—C1—C2	115.84 (12)	C5^i—C5—H5A	109.7
N1—C2—C1	113.27 (11)	N2—C5—H5B	109.7
N1—C2—H2A	108.9	C5^i—C5—H5B	109.7
C1—C2—H2A	108.9	H5A—C5—H5B	108.2
N1—C2—H2B	108.9	C3—N1—C2	114.61 (11)
C1—C2—H2B	108.9	C3—N1—H1B	110.3 (11)
H2A—C2—H2B	107.7	C2—N1—H1B	107.4 (11)
N1—C3—C4	110.90 (12)	C3—N1—H1A	108.1 (11)
N1—C3—H3A	109.5	C2—N1—H1A	109.6 (11)
C4—C3—H3A	109.5	H1B—N1—H1A	106.5 (15)
N1—C3—H3B	109.5	C5—N2—H2E	110.3 (12)
C4—C3—H3B	109.5	C5—N2—H2C	111.7 (12)
H3A—C3—H3B	108.0	H2E—N2—H2C	108.5 (16)
O4—C4—O3	126.73 (14)	C5—N2—H2D	108.1 (12)
O4—C4—C3	118.05 (13)	H2E—N2—H2D	111.6 (16)
O3—C4—C3	115.22 (13)	H2C—N2—H2D	106.6 (17)
O2—C1—C2—N1	−19.90 (18)	N1—C3—C4—O3	−151.42 (14)
O1—C1—C2—N1	161.40 (12)	C4—C3—N1—C2	−172.36 (12)
N1—C3—C4—O4	28.56 (19)	C1—C2—N1—C3	−64.75 (16)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O4^ii	0.97	2.45	3.2667 (19)	142
C3—H3A···O2	0.97	2.56	3.0997 (19)	115
C3—H3B···O4^ii	0.97	2.44	3.2875 (19)	146
N1—H1B···O2^iii	0.927 (19)	1.908 (19)	2.7853 (16)	157.0 (16)
N1—H1A···O1^iv	0.895 (19)	1.897 (19)	2.7856 (16)	172.2 (16)
N2—H2E···O4^v	0.90 (2)	1.99 (2)	2.8174 (17)	152.1 (16)
N2—H2C···O3^ii	0.94 (2)	1.77 (2)	2.7042 (18)	169.1 (17)
N2—H2D···O1^vi	0.91 (2)	1.93 (2)	2.8255 (17)	168.5 (18)

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