Amino­pyrimidine–carboxyl­(ate) interactions in trimethoprim maleate, an antifolate drug

In the title cocrystal, trimethoprim maleate [2,4-di­amino-5-(3,4,5-tri­methoxy­benzyl)­pyrimidin-1-ium maleate], C₁₄H₁₉­N₄O₃⁺·­C₄H₃O₄⁻, the trimethoprim mol­ecule is protonated at N1. The carboxyl group of the maleate ion makes a specific double hydrogen bond of type N—H...O with the 2-amino group and the protonated N1 atom of the trimethoprim cation which is similar to the carboxyl­ate–trimethoprim cation interaction observed in the complex of di­hydro­folate reductase with trimethoprim. The pyrimidine moieties of trimethoprim cations are centrosymmetrically paired through a pair of N—H...N hydrogen bonds involving the 4-amino group and the pyridinium N3 atom of a symmetry-related molecule. One of the O atoms at the maleate carboxyl­ate group bridges the 2-­amino and 4-amino groups on either side of the paired trimethoprim cations. The other O atom of the carboxyl­ate group forms an intramolecular O—H...O hydrogen bond with the carboxyl group. These characteristic hydrogen bonds result in infinite two-dimensional aggregation of rings into a supramolecular ladder, which is further crosslinked through weak C—H...O interactions with methoxy groups of neighbouring trimethoprim mol­ecules to form a layered structure.

Computing details

Data collection: MolEN (Fair, 1990); cell refinement: MolEN; data reduction: MolEN; program(s) used to solve structure: SHELXL97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1997); software used to prepare material for publication: PLATON.

(I)

Crystal data

C14H19N4O3^+·C4H3O4^−	F(000) = 856
Mr = 406.40	Dx = 1.353 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 40 reflections
a = 28.485 (2) Å	θ = 6.8–21.3°
b = 12.964 (3) Å	µ = 0.89 mm^−1
c = 5.413 (2) Å	T = 293 K
β = 93.27 (3)°	Plate, pale yellow
V = 1995.7 (9) Å^3	0.31 × 0.26 × 0.17 mm
Z = 4

Data collection

Enraf-Nonius CAD-4 diffractometer	1522 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
Graphite monochromator	θmax = 70.0°, θmin = 3.1°
ω–2θ scans	h = −10→34
Absorption correction: ψ scan (North et al., 1968)	k = −14→15
Tmin = 0.757, Tmax = 0.863	l = −6→6
4200 measured reflections	3 standard reflections every 60 min
3796 independent reflections	intensity decay: none

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.1407P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.065	(Δ/σ)max < 0.001
wR(F^2) = 0.257	Δρmax = 0.28 e Å^−3
S = 0.91	Δρmin = −0.26 e Å^−3
3796 reflections	Extinction correction: shelxl, FC^*=KFC[1+0.001XFC^2Λ^3/SIN(2Θ)]^-1/4
278 parameters	Extinction coefficient: 0.0017 (5)
0 restraints

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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

	x	y	z	Uiso*/Ueq
O1	0.21895 (12)	0.3024 (3)	0.4220 (8)	0.0842 (14)
O2	0.25953 (11)	0.1254 (3)	0.3000 (7)	0.0784 (14)
O3	0.23285 (14)	−0.0537 (3)	0.4932 (8)	0.0933 (18)
N1	0.06606 (12)	−0.1333 (3)	1.1442 (7)	0.0601 (12)
N2	0.00963 (13)	−0.2302 (3)	0.9361 (7)	0.0619 (14)
N3	0.02812 (11)	−0.0719 (3)	0.7773 (7)	0.0513 (11)
N4	0.04689 (12)	0.0874 (3)	0.6292 (7)	0.0573 (12)
C1'	0.15639 (14)	0.1234 (3)	0.8153 (9)	0.0583 (16)
C2	0.03454 (14)	−0.1454 (3)	0.9531 (9)	0.0520 (14)
C2'	0.16910 (15)	0.2151 (3)	0.7059 (9)	0.0595 (14)
C3'	0.20366 (15)	0.2156 (3)	0.5385 (10)	0.0588 (16)
C4	0.05401 (14)	0.0156 (3)	0.8017 (8)	0.0499 (14)
C4'	0.22543 (15)	0.1249 (4)	0.4735 (10)	0.0631 (16)
C5	0.08861 (15)	0.0304 (3)	1.0012 (9)	0.0518 (14)
C5'	0.21124 (16)	0.0326 (3)	0.5765 (10)	0.0632 (17)
C6	0.09264 (15)	−0.0468 (4)	1.1702 (9)	0.0569 (16)
C6'	0.17685 (16)	0.0306 (4)	0.7466 (10)	0.0642 (19)
C7	0.12015 (15)	0.1240 (3)	1.0122 (9)	0.0595 (16)
C8	0.1942 (2)	0.3974 (4)	0.4513 (14)	0.112 (3)
C9	0.30535 (18)	0.1346 (5)	0.4060 (13)	0.109 (3)
C10	0.2148 (2)	−0.1506 (4)	0.5577 (13)	0.093 (3)
O4	0.05312 (15)	−0.3859 (3)	1.2700 (8)	0.0915 (18)
O5	0.08854 (14)	−0.2717 (3)	1.5165 (7)	0.0833 (16)
O6	0.04228 (14)	−0.5712 (3)	1.2529 (7)	0.0869 (16)
O7	0.05492 (14)	−0.7021 (3)	1.5007 (8)	0.0924 (16)
C11	0.07443 (17)	−0.3612 (4)	1.4753 (10)	0.0634 (19)
C12	0.08083 (18)	−0.4390 (4)	1.6728 (10)	0.0705 (19)
C13	0.07323 (18)	−0.5395 (4)	1.6710 (10)	0.0693 (17)
C14	0.05594 (17)	−0.6094 (4)	1.4660 (11)	0.0640 (19)
H1	0.06950	−0.18150	1.25290	0.082 (18)*
H2'	0.15430	0.27630	0.74570	0.066 (14)*
H2A	0.01360	−0.27740	1.04700	0.056 (7)*
H2B	−0.01070	−0.23870	0.81420	0.056 (7)*
H4A	0.02650	0.07730	0.50820	0.056 (7)*
H4B	0.06260	0.14400	0.63830	0.056 (7)*
H6	0.11400	−0.04030	1.30590	0.094 (19)*
H6'	0.16750	−0.03150	0.81420	0.074 (15)*
H7A	0.13640	0.12740	1.17430	0.122 (7)*
H7B	0.10090	0.18550	0.99170	0.122 (7)*
H8A	0.20920	0.45110	0.36230	0.122 (7)*
H8B	0.19470	0.41510	0.62360	0.122 (7)*
H8C	0.16230	0.38980	0.38760	0.122 (7)*
H9A	0.30910	0.20110	0.48280	0.122 (7)*
H9B	0.32740	0.12750	0.27960	0.122 (7)*
H9C	0.31090	0.08160	0.52810	0.122 (7)*
H10A	0.23280	−0.20420	0.48580	0.122 (7)*
H10B	0.18250	−0.15580	0.49670	0.122 (7)*
H10C	0.21660	−0.15780	0.73450	0.122 (7)*
H4	0.048 (2)	−0.467 (5)	1.273 (12)	0.12 (2)*
H12	0.09220	−0.41290	1.82470	0.071 (16)*
H13	0.07970	−0.57210	1.82220	0.11 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.083 (2)	0.056 (2)	0.118 (3)	−0.0030 (17)	0.043 (2)	0.011 (2)
O2	0.065 (2)	0.078 (2)	0.095 (3)	0.0001 (17)	0.029 (2)	0.002 (2)
O3	0.096 (3)	0.060 (2)	0.129 (4)	0.0098 (19)	0.050 (3)	0.002 (2)
N1	0.054 (2)	0.068 (2)	0.058 (2)	0.0016 (18)	0.0012 (18)	0.015 (2)
N2	0.074 (2)	0.053 (2)	0.058 (3)	−0.0060 (18)	−0.003 (2)	0.0100 (18)
N3	0.0501 (19)	0.0469 (19)	0.057 (2)	0.0019 (15)	0.0050 (16)	−0.0008 (17)
N4	0.060 (2)	0.053 (2)	0.058 (2)	−0.0043 (17)	−0.0046 (18)	0.0032 (19)
C1'	0.043 (2)	0.060 (3)	0.072 (3)	−0.0075 (19)	0.005 (2)	−0.001 (2)
C2	0.050 (2)	0.048 (2)	0.058 (3)	0.0026 (19)	0.004 (2)	0.003 (2)
C2'	0.058 (2)	0.048 (2)	0.073 (3)	0.006 (2)	0.009 (2)	0.002 (2)
C3'	0.051 (2)	0.044 (2)	0.082 (4)	0.0017 (19)	0.008 (2)	0.005 (2)
C4	0.047 (2)	0.051 (2)	0.052 (3)	0.0070 (18)	0.006 (2)	0.000 (2)
C4'	0.049 (2)	0.065 (3)	0.077 (3)	0.000 (2)	0.019 (2)	0.006 (3)
C5	0.052 (2)	0.049 (2)	0.055 (3)	0.0030 (18)	0.009 (2)	−0.003 (2)
C5'	0.060 (3)	0.054 (3)	0.077 (3)	0.006 (2)	0.016 (2)	−0.001 (3)
C6	0.044 (2)	0.063 (3)	0.064 (3)	0.002 (2)	0.006 (2)	0.001 (2)
C6'	0.059 (3)	0.055 (3)	0.079 (4)	−0.004 (2)	0.008 (2)	0.004 (2)
C7	0.050 (2)	0.062 (3)	0.067 (3)	−0.006 (2)	0.007 (2)	−0.004 (2)
C8	0.122 (5)	0.058 (3)	0.162 (7)	0.006 (3)	0.065 (5)	0.020 (4)
C9	0.063 (3)	0.125 (6)	0.144 (7)	−0.001 (3)	0.039 (4)	−0.020 (5)
C10	0.095 (4)	0.064 (3)	0.124 (6)	0.015 (3)	0.032 (4)	−0.001 (3)
O4	0.132 (4)	0.063 (2)	0.077 (3)	−0.005 (2)	−0.015 (3)	0.013 (2)
O5	0.111 (3)	0.059 (2)	0.080 (3)	−0.0064 (19)	0.007 (2)	0.0093 (19)
O6	0.121 (3)	0.063 (2)	0.074 (3)	−0.017 (2)	−0.018 (2)	0.0071 (19)
O7	0.111 (3)	0.060 (2)	0.104 (3)	−0.008 (2)	−0.012 (2)	0.014 (2)
C11	0.063 (3)	0.053 (3)	0.075 (4)	0.005 (2)	0.011 (3)	0.004 (3)
C12	0.079 (3)	0.069 (3)	0.064 (4)	0.003 (3)	0.008 (3)	0.005 (3)
C13	0.079 (3)	0.072 (3)	0.057 (3)	0.011 (3)	0.004 (3)	0.017 (3)
C14	0.067 (3)	0.051 (3)	0.075 (4)	0.001 (2)	0.013 (3)	0.007 (3)

Geometric parameters (Å, º)

O1—C3'	1.373 (6)	C3'—C4'	1.384 (6)
O1—C8	1.432 (7)	C4—C5	1.433 (6)
O2—C4'	1.389 (6)	C4'—C5'	1.390 (7)
O2—C9	1.401 (6)	C5—C7	1.509 (6)
O3—C5'	1.366 (6)	C5—C6	1.356 (7)
O3—C10	1.409 (7)	C5'—C6'	1.382 (7)
O4—C11	1.276 (7)	C2'—H2'	0.9295
O5—C11	1.244 (6)	C6—H6	0.9305
O6—C14	1.295 (7)	C6'—H6'	0.9296
O7—C14	1.217 (7)	C7—H7B	0.9704
O4—H4	1.06 (6)	C7—H7A	0.9694
N1—C6	1.356 (6)	C8—H8A	0.9606
N1—C2	1.340 (6)	C8—H8C	0.9584
N2—C2	1.309 (6)	C8—H8B	0.9598
N3—C2	1.352 (6)	C9—H9B	0.9592
N3—C4	1.355 (5)	C9—H9C	0.9602
N4—C4	1.326 (6)	C9—H9A	0.9604
N1—H1	0.8601	C10—H10C	0.9600
N2—H2B	0.8598	C10—H10A	0.9592
N2—H2A	0.8601	C10—H10B	0.9620
N4—H4A	0.8603	C11—C12	1.473 (8)
N4—H4B	0.8594	C12—C13	1.321 (7)
C1'—C7	1.526 (6)	C13—C14	1.494 (8)
C1'—C6'	1.396 (6)	C12—H12	0.9301
C1'—C2'	1.385 (6)	C13—H13	0.9302
C2'—C3'	1.376 (7)
O1···O2	2.669 (5)	C5'···H9C	2.9353
O1···C9	3.290 (7)	C6···H6'	2.9612
O1···C10^i	3.352 (8)	C6'···H10C	2.6945
O1···C10^ii	3.355 (8)	C6'···H10B	2.7785
O2···O3	2.674 (6)	C6'···H6^v	3.0419
O2···O1	2.669 (5)	C7···H4B	2.5441
O3···C9	3.249 (7)	C8···H10C^ii	3.0607
O3···O2	2.674 (6)	C8···H2'	2.5500
O3···C8^iii	3.329 (8)	C9···H8A^iii	2.8056
O4···N2	2.936 (6)	C10···H6'	2.5180
O4···O6	2.423 (6)	C11···H2A	3.0165
O4···C14	3.085 (7)	C11···H1	2.6224
O5···N1	2.747 (6)	C13···H4	2.42 (6)
O5···C2^iv	3.324 (6)	C14···H4	2.13 (6)
O6···C11	3.094 (7)	C14···H8C^vii	3.0831
O6···C13^v	3.344 (7)	C14···H2B^vi	2.7597
O6···O4	2.423 (6)	H1···O5	1.8998
O6···N2^vi	3.113 (6)	H1···C11	2.6224
O7···N4^vii	2.829 (6)	H1···O4	2.6931
O7···N2^vi	3.041 (6)	H1···H2A	2.2629
O1···H10C^ii	2.5893	H2'···C8	2.5500
O1···H9A	2.8863	H2'···H7B	2.3882
O1···H10A^i	2.6674	H2'···H8C	2.4545
O2···H10A^i	2.7129	H2'···H8B	2.2552
O2···H8A^iii	2.6001	H2A···C11	3.0165
O3···H9C	2.8297	H2A···H1	2.2629
O3···H8A^iii	2.6065	H2A···O4	2.1326
O3···H8B^viii	2.8700	H2B···O6^vi	2.6415
O4···H1	2.6931	H2B···O7^vi	2.1991
O4···H12^v	2.7346	H2B···C14^vi	2.7597
O4···H2A	2.1326	H4···O6	1.36 (6)
O5···H1	1.8998	H4···C13	2.42 (6)
O6···H13^v	2.6182	H4···C14	2.13 (6)
O6···H4	1.36 (6)	H4A···N3^ix	2.1306
O6···H2B^vi	2.6415	H4A···C2^ix	3.0891
O7···H4B^vii	2.1365	H4A···C4^ix	3.0141
O7···H2B^vi	2.1991	H4A···H4A^ix	2.5077
N1···O5	2.747 (6)	H4B···O7^xi	2.1365
N2···O4	2.936 (6)	H4B···C1'	2.7991
N2···O6^vi	3.113 (6)	H4B···C7	2.5441
N2···O7^vi	3.041 (6)	H4B···H7B	2.2138
N3···N4^ix	2.985 (5)	H6···C6'^iv	3.0419
N3···C4^x	3.436 (6)	H6···H7A	2.3860
N4···O7^xi	2.829 (6)	H6'···C5	2.6416
N4···C1'	3.256 (5)	H6'···C6	2.9612
N4···C6^v	3.357 (6)	H6'···C10	2.5180
N4···N3^ix	2.985 (5)	H6'···H10C	2.2118
N4···C2^x	3.414 (6)	H6'···H10B	2.4118
N3···H4A^ix	2.1306	H7A···C4'^iv	2.9303
N4···H7B	2.7368	H7A···H6	2.3860
C1'···N4	3.256 (5)	H7A···C3'^iv	2.9041
C2···O5^v	3.324 (6)	H7B···N4	2.7368
C2···C4^x	3.367 (6)	H7B···H2'	2.3882
C2···N4^x	3.414 (6)	H7B···H4B	2.2138
C3'···C10^ii	3.550 (8)	H8A···O2^i	2.6001
C4···C2^x	3.367 (6)	H8A···O3^i	2.6065
C4···N3^x	3.436 (6)	H8A···C9^i	2.8056
C4···C6'	3.534 (6)	H8B···H2'	2.2552
C6···C6'	3.556 (7)	H8B···O3^ii	2.8700
C6···N4^iv	3.357 (6)	H8B···C2'	2.7368
C6'···C4	3.534 (6)	H8C···C14^xi	3.0831
C6'···C6	3.556 (7)	H8C···H2'	2.4545
C8···O3^i	3.329 (8)	H8C···C2'	2.8456
C9···O1	3.290 (7)	H9A···C3'	3.0414
C9···O3	3.249 (7)	H9A···H10C^ii	2.5202
C10···O1^viii	3.355 (8)	H9A···O1	2.8863
C10···O1^iii	3.352 (8)	H9C···O3	2.8297
C10···C3'^viii	3.550 (8)	H9C···C5'	2.9353
C11···O6	3.094 (7)	H10A···O2^iii	2.7129
C13···O6^iv	3.344 (7)	H10A···O1^iii	2.6674
C14···O4	3.085 (7)	H10B···C6'	2.7785
C1'···H4B	2.7991	H10B···H6'	2.4118
C2···H4A^ix	3.0891	H10C···H6'	2.2118
C2'···H8B	2.7368	H10C···O1^viii	2.5893
C2'···H8C	2.8456	H10C···C6'	2.6945
C3'···H7A^v	2.9041	H10C···C8^viii	3.0607
C3'···H9A	3.0414	H10C···H9A^viii	2.5202
C3'···H10C^ii	3.0074	H10C···C3'^viii	3.0074
C4···H4A^ix	3.0141	H12···O4^iv	2.7346
C4'···H7A^v	2.9303	H13···O6^iv	2.6182
C5···H6'	2.6416
C3'—O1—C8	118.9 (4)	C1'—C2'—H2'	120.02
C4'—O2—C9	113.2 (4)	N1—C6—H6	119.53
C5'—O3—C10	118.1 (4)	C5—C6—H6	119.47
C11—O4—H4	107 (3)	C1'—C6'—H6'	120.53
C2—N1—C6	121.5 (4)	C5'—C6'—H6'	120.55
C2—N3—C4	118.1 (4)	C1'—C7—H7B	108.95
C6—N1—H1	119.26	C5—C7—H7A	108.95
C2—N1—H1	119.23	C5—C7—H7B	108.96
C2—N2—H2A	119.95	H7A—C7—H7B	107.68
H2A—N2—H2B	120.03	C1'—C7—H7A	108.99
C2—N2—H2B	120.02	O1—C8—H8A	109.38
C4—N4—H4A	119.92	O1—C8—H8C	109.53
H4A—N4—H4B	120.02	H8A—C8—H8B	109.37
C4—N4—H4B	120.05	O1—C8—H8B	109.45
C2'—C1'—C6'	120.1 (4)	H8B—C8—H8C	109.60
C2'—C1'—C7	119.9 (4)	H8A—C8—H8C	109.50
C6'—C1'—C7	120.0 (4)	O2—C9—H9A	109.38
N2—C2—N3	119.4 (4)	O2—C9—H9B	109.42
N1—C2—N3	121.3 (4)	H9A—C9—H9B	109.49
N1—C2—N2	119.3 (4)	H9A—C9—H9C	109.54
C1'—C2'—C3'	120.0 (4)	O2—C9—H9C	109.51
O1—C3'—C4'	114.9 (4)	H9B—C9—H9C	109.48
C2'—C3'—C4'	120.8 (4)	O3—C10—H10B	109.44
O1—C3'—C2'	124.3 (4)	O3—C10—H10C	109.53
N3—C4—C5	122.2 (4)	H10A—C10—H10B	109.44
N4—C4—C5	120.5 (4)	H10A—C10—H10C	109.55
N3—C4—N4	117.3 (4)	H10B—C10—H10C	109.33
O2—C4'—C5'	120.4 (4)	O3—C10—H10A	109.53
C3'—C4'—C5'	119.0 (4)	O4—C11—O5	121.5 (5)
O2—C4'—C3'	120.6 (4)	O5—C11—C12	118.9 (5)
C6—C5—C7	122.6 (4)	O4—C11—C12	119.5 (5)
C4—C5—C7	121.3 (4)	C11—C12—C13	131.0 (5)
C4—C5—C6	116.0 (4)	C12—C13—C14	130.6 (5)
O3—C5'—C6'	123.7 (4)	O6—C14—C13	120.0 (5)
O3—C5'—C4'	115.2 (4)	O7—C14—C13	119.6 (5)
C4'—C5'—C6'	121.1 (4)	O6—C14—O7	120.4 (5)
N1—C6—C5	121.0 (4)	C11—C12—H12	114.51
C1'—C6'—C5'	118.9 (4)	C13—C12—H12	114.46
C1'—C7—C5	113.2 (4)	C12—C13—H13	114.68
C3'—C2'—H2'	119.98	C14—C13—H13	114.72
C8—O1—C3'—C4'	171.6 (5)	C2'—C3'—C4'—O2	178.5 (4)
C8—O1—C3'—C2'	−7.7 (8)	C2'—C3'—C4'—C5'	1.2 (7)
C9—O2—C4'—C5'	−89.6 (6)	O1—C3'—C4'—C5'	−178.1 (4)
C9—O2—C4'—C3'	93.1 (6)	N4—C4—C5—C7	−4.2 (6)
C10—O3—C5'—C6'	9.0 (8)	N3—C4—C5—C6	−2.5 (6)
C10—O3—C5'—C4'	−169.6 (5)	N3—C4—C5—C7	174.3 (4)
C2—N1—C6—C5	−0.8 (7)	N4—C4—C5—C6	178.9 (4)
C6—N1—C2—N2	−179.9 (4)	C3'—C4'—C5'—C6'	−1.8 (8)
C6—N1—C2—N3	0.4 (7)	O2—C4'—C5'—O3	−0.4 (7)
C4—N3—C2—N1	−1.1 (6)	O2—C4'—C5'—C6'	−179.0 (5)
C2—N3—C4—C5	2.2 (6)	C3'—C4'—C5'—O3	176.9 (5)
C4—N3—C2—N2	179.2 (4)	C4—C5—C7—C1'	−70.0 (5)
C2—N3—C4—N4	−179.2 (4)	C4—C5—C6—N1	1.8 (6)
C2'—C1'—C6'—C5'	2.8 (7)	C7—C5—C6—N1	−175.0 (4)
C6'—C1'—C7—C5	−36.1 (6)	C6—C5—C7—C1'	106.6 (5)
C7—C1'—C2'—C3'	176.4 (4)	C4'—C5'—C6'—C1'	−0.2 (8)
C6'—C1'—C2'—C3'	−3.3 (7)	O3—C5'—C6'—C1'	−178.7 (5)
C7—C1'—C6'—C5'	−176.9 (4)	O5—C11—C12—C13	−173.0 (6)
C2'—C1'—C7—C5	144.2 (4)	O4—C11—C12—C13	9.6 (9)
C1'—C2'—C3'—O1	−179.5 (4)	C11—C12—C13—C14	0.8 (10)
C1'—C2'—C3'—C4'	1.3 (7)	C12—C13—C14—O7	174.3 (6)
O1—C3'—C4'—O2	−0.8 (7)	C12—C13—C14—O6	−5.5 (9)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5	0.8601	1.8998	2.747 (6)	167.83
N2—H2A···O4	0.8601	2.1326	2.936 (6)	155.29
N2—H2B···O7^vi	0.8598	2.1991	3.041 (6)	166.04
O4—H4···O6	1.06 (6)	1.36 (6)	2.423 (6)	174 (6)
N4—H4A···N3^ix	0.8603	2.1306	2.985 (5)	172.14
N4—H4B···O7^xi	0.8594	2.1365	2.829 (6)	137.28
C10—H10C···O1^viii	0.9600	2.5893	3.355 (8)	136.94

Symmetry codes: (vi) −x, −y−1, −z+2; (viii) −x+1/2, y−1/2, −z+3/2; (ix) −x, −y, −z+1; (xi) x, y+1, z−1.