Four cocrystals of thymine with phenolic coformers: influence of the coformer on hydrogen bonding

Cocrystals are mol­ecular solids composed of at least two types of neutral chemical species held together by noncovalent forces. Crystallization of thymine [systematic name: 5-methyl­pyrimidine-2,4(1H,3H)-dione] with four phenolic coformers resulted in cocrystal formation, viz. catechol (benzene-1,2-diol) giving thymine-catechol (1/1), C₅H₆N₂O₂·C₆H₆O₂, (I), resorcinol (benzene-1,3-diol) giving thymine-resorcinol (2/1), 2C₅H₆N₂O₂·C₆H₆O₂, (II), hydro­quinone (benzene-1,4-diol) giving thymine-hydro­quinone (2/1), 2C₅H₆N₂O₂·C₆H₆O₂, (III), and pyrogallol (benzene-1,2,3-triol) giving thymine-pyrogallol (1/2), C₅H₆N₂O₂·2C₆H₆O₃, (IV). The resorcinol mol­ecule in (II) occupies a twofold axis, while the hydro­quinone mol­ecule in (III) is situated on a centre of inversion. Thymine-thymine base pairing is common across all four structures, albeit with different patterns. In (I)-(III), the base pair is propagated into an infinite one-dimensional ribbon, whereas it exists as a discrete dimeric unit in (IV). In (I)-(III), the two donor N atoms and one carbonyl acceptor O atom of thymine are involved in thymine-thymine base pairing and the remaining carbonyl O atom is hydrogen bonded to the coformer. In contrast, in (IV), just one donor N atom and one acceptor O atom are involved in base pairing, and the remaining donor N atom and acceptor O atom of thymine form hydrogen bonds to the coformer mol­ecules. Thus, the utilization of the donor and acceptor atoms of thymine in the hydrogen bonding is influenced by the coformers.

Computing details

For all compounds, data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

(I) 5-Methylpyrimidine-2,4(1H,3H)-dione–benzene-1,2-diol (1/1)

Crystal data

C5H6N2O2·C6H6O2	Dx = 1.368 Mg m^−3
Mr = 236.23	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 7224 reflections
a = 6.9132 (8) Å	θ = 3.2–27.6°
b = 8.9917 (10) Å	µ = 0.11 mm^−1
c = 36.898 (4) Å	T = 294 K
V = 2293.6 (4) Å^3	Block, colourless
Z = 8	0.18 × 0.15 × 0.08 mm
F(000) = 992

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2311 reflections with I > 2σ(I)
ω scans	Rint = 0.030
Absorption correction: multi-scan (SADABS; Bruker, 2001)	θmax = 28.2°, θmin = 2.2°
Tmin = 0.93, Tmax = 0.98	h = −8→8
24525 measured reflections	k = −11→11
2768 independent reflections	l = −47→48

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.134	w = 1/[σ^2(Fo^2) + (0.0581P)^2 + 0.5148P] where P = (Fo^2 + 2Fc^2)/3
S = 1.17	(Δ/σ)max < 0.001
2768 reflections	Δρmax = 0.23 e Å^−3
171 parameters	Δρmin = −0.17 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
C2	0.06793 (18)	0.17018 (16)	0.47840 (4)	0.0351 (3)
C4	−0.11589 (19)	0.00171 (16)	0.43924 (4)	0.0367 (3)
C5	0.06574 (19)	−0.05643 (17)	0.42554 (4)	0.0385 (3)
C6	0.2295 (2)	−0.00084 (17)	0.43921 (4)	0.0401 (3)
H6	0.3468	−0.0383	0.4309	0.048*
C9	0.0594 (2)	−0.1761 (2)	0.39744 (5)	0.0512 (4)
H9A	0.1883	−0.2104	0.3926	0.077*
H9B	0.0035	−0.1373	0.3756	0.077*
H9C	−0.0178	−0.2574	0.4061	0.077*
N1	0.23193 (17)	0.10980 (14)	0.46510 (3)	0.0399 (3)
H1N	0.339 (3)	0.145 (2)	0.4743 (5)	0.051 (5)*
N3	−0.09944 (16)	0.11398 (14)	0.46474 (3)	0.0381 (3)
H2N	−0.206 (3)	0.154 (2)	0.4732 (5)	0.048 (5)*
O7	0.06794 (13)	0.26938 (13)	0.50170 (3)	0.0444 (3)
O8	−0.27799 (14)	−0.04084 (14)	0.43056 (3)	0.0483 (3)
C10	−0.4722 (3)	−0.0185 (2)	0.33773 (5)	0.0526 (4)
C11	−0.3432 (3)	0.09660 (19)	0.33232 (5)	0.0517 (4)
C12	−0.3707 (3)	0.1932 (2)	0.30377 (5)	0.0667 (5)
H12	−0.2861	0.2724	0.3003	0.080*
C13	−0.5229 (4)	0.1726 (3)	0.28038 (6)	0.0819 (7)
H13	−0.5413	0.2379	0.2611	0.098*
C14	−0.6477 (4)	0.0561 (3)	0.28534 (7)	0.0901 (8)
H14	−0.7490	0.0413	0.2692	0.108*
C15	−0.6239 (3)	−0.0396 (3)	0.31421 (6)	0.0757 (6)
H15	−0.7099	−0.1178	0.3177	0.091*
O16	−0.44933 (18)	−0.11560 (15)	0.36626 (4)	0.0579 (3)
H1O	−0.370 (3)	−0.079 (3)	0.3818 (7)	0.082 (7)*
O17	−0.1939 (2)	0.10467 (17)	0.35633 (4)	0.0641 (4)
H2O	−0.139 (4)	0.189 (3)	0.3564 (7)	0.084 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0254 (6)	0.0405 (7)	0.0396 (7)	−0.0015 (5)	−0.0004 (5)	−0.0012 (6)
C4	0.0288 (6)	0.0439 (7)	0.0374 (7)	−0.0023 (5)	−0.0026 (5)	−0.0004 (6)
C5	0.0324 (7)	0.0399 (7)	0.0431 (7)	0.0007 (6)	0.0008 (5)	−0.0022 (6)
C6	0.0284 (7)	0.0436 (8)	0.0483 (8)	0.0025 (6)	0.0051 (6)	−0.0043 (6)
C9	0.0427 (8)	0.0524 (9)	0.0585 (10)	0.0051 (7)	−0.0029 (7)	−0.0156 (8)
N1	0.0226 (6)	0.0473 (7)	0.0498 (7)	−0.0022 (5)	−0.0003 (5)	−0.0070 (5)
N3	0.0221 (6)	0.0469 (7)	0.0452 (7)	0.0009 (5)	0.0007 (5)	−0.0069 (5)
O7	0.0258 (5)	0.0555 (7)	0.0518 (6)	−0.0013 (4)	−0.0003 (4)	−0.0158 (5)
O8	0.0299 (5)	0.0628 (7)	0.0521 (6)	−0.0069 (5)	−0.0040 (4)	−0.0120 (5)
C10	0.0514 (9)	0.0550 (10)	0.0515 (9)	0.0074 (8)	−0.0032 (7)	−0.0092 (8)
C11	0.0541 (9)	0.0507 (9)	0.0502 (9)	0.0108 (8)	0.0025 (7)	−0.0100 (7)
C12	0.0778 (13)	0.0634 (11)	0.0591 (11)	0.0117 (10)	0.0080 (10)	−0.0021 (9)
C13	0.1006 (18)	0.0892 (16)	0.0558 (11)	0.0267 (15)	−0.0066 (12)	0.0045 (11)
C14	0.0838 (16)	0.116 (2)	0.0706 (14)	0.0163 (16)	−0.0276 (12)	−0.0046 (14)
C15	0.0668 (12)	0.0881 (15)	0.0720 (13)	−0.0037 (12)	−0.0187 (10)	−0.0074 (12)
O16	0.0549 (8)	0.0580 (7)	0.0608 (7)	−0.0082 (6)	−0.0127 (6)	−0.0040 (6)
O17	0.0592 (8)	0.0574 (8)	0.0756 (9)	−0.0076 (6)	−0.0117 (6)	0.0058 (7)

Geometric parameters (Å, º)

C2—O7	1.2387 (17)	C10—C15	1.374 (3)
C2—N1	1.3495 (17)	C10—O16	1.377 (2)
C2—N3	1.3595 (17)	C10—C11	1.380 (3)
C4—O8	1.2267 (17)	C11—O17	1.362 (2)
C4—N3	1.3847 (19)	C11—C12	1.378 (3)
C4—C5	1.4510 (19)	C12—C13	1.374 (3)
C5—C6	1.336 (2)	C12—H12	0.9300
C5—C9	1.495 (2)	C13—C14	1.369 (4)
C6—N1	1.3795 (19)	C13—H13	0.9300
C6—H6	0.9300	C14—C15	1.379 (4)
C9—H9A	0.9600	C14—H14	0.9300
C9—H9B	0.9600	C15—H15	0.9300
C9—H9C	0.9600	O16—H1O	0.86 (3)
N1—H1N	0.871 (19)	O17—H2O	0.85 (3)
N3—H2N	0.881 (19)
O7—C2—N1	122.82 (12)	C2—N3—H2N	115.5 (12)
O7—C2—N3	121.67 (12)	C4—N3—H2N	118.1 (12)
N1—C2—N3	115.51 (13)	C15—C10—O16	118.86 (18)
O8—C4—N3	118.67 (12)	C15—C10—C11	120.32 (19)
O8—C4—C5	125.96 (13)	O16—C10—C11	120.81 (15)
N3—C4—C5	115.36 (12)	O17—C11—C12	124.60 (18)
C6—C5—C4	117.84 (13)	O17—C11—C10	115.79 (16)
C6—C5—C9	123.77 (13)	C12—C11—C10	119.61 (18)
C4—C5—C9	118.39 (12)	C13—C12—C11	120.0 (2)
C5—C6—N1	122.78 (13)	C13—C12—H12	120.0
C5—C6—H6	118.6	C11—C12—H12	120.0
N1—C6—H6	118.6	C14—C13—C12	120.1 (2)
C5—C9—H9A	109.5	C14—C13—H13	119.9
C5—C9—H9B	109.5	C12—C13—H13	119.9
H9A—C9—H9B	109.5	C13—C14—C15	120.4 (2)
C5—C9—H9C	109.5	C13—C14—H14	119.8
H9A—C9—H9C	109.5	C15—C14—H14	119.8
H9B—C9—H9C	109.5	C10—C15—C14	119.5 (2)
C2—N1—C6	122.13 (12)	C10—C15—H15	120.2
C2—N1—H1N	115.0 (12)	C14—C15—H15	120.2
C6—N1—H1N	122.8 (12)	C10—O16—H1O	109.8 (16)
C2—N3—C4	126.36 (12)	C11—O17—H2O	113.0 (17)
O8—C4—C5—C6	−177.21 (15)	C5—C4—N3—C2	−1.9 (2)
N3—C4—C5—C6	1.9 (2)	C15—C10—C11—O17	−177.65 (18)
O8—C4—C5—C9	2.0 (2)	O16—C10—C11—O17	1.1 (2)
N3—C4—C5—C9	−178.95 (13)	C15—C10—C11—C12	2.0 (3)
C4—C5—C6—N1	−1.0 (2)	O16—C10—C11—C12	−179.28 (16)
C9—C5—C6—N1	179.90 (15)	O17—C11—C12—C13	177.97 (18)
O7—C2—N1—C6	179.88 (14)	C10—C11—C12—C13	−1.6 (3)
N3—C2—N1—C6	0.4 (2)	C11—C12—C13—C14	0.0 (3)
C5—C6—N1—C2	−0.2 (2)	C12—C13—C14—C15	1.3 (4)
O7—C2—N3—C4	−178.76 (14)	O16—C10—C15—C14	−179.5 (2)
N1—C2—N3—C4	0.7 (2)	C11—C10—C15—C14	−0.7 (3)
O8—C4—N3—C2	177.31 (14)	C13—C14—C15—C10	−1.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O7^i	0.871 (19)	1.973 (19)	2.842 (2)	176 (2)
N3—H2N···O7^ii	0.881 (19)	1.939 (19)	2.814 (2)	172 (2)
O16—H1O···O8	0.86 (3)	1.94 (3)	2.736 (2)	154 (2)
O16—H1O···O17	0.86 (3)	2.26 (2)	2.678 (2)	110.4 (19)
O17—H2O···O16^iii	0.85 (3)	1.89 (3)	2.728 (2)	167 (2)

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

(II) 5-Methylpyrimidine-2,4(1H,3H)-dione–benzene-1,3-diol (2/1)

Crystal data

2C5H6N2O2·C6H6O2	Dx = 1.430 Mg m^−3
Mr = 362.34	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 5292 reflections
a = 6.9499 (7) Å	θ = 3.0–27.8°
b = 9.0237 (10) Å	µ = 0.11 mm^−1
c = 26.828 (3) Å	T = 294 K
V = 1682.5 (3) Å^3	Needle, colourless
Z = 4	0.18 × 0.11 × 0.09 mm
F(000) = 760

Data collection

Bruker SMART APEX CCD area-detector diffractometer	1804 reflections with I > 2σ(I)
ω scans	Rint = 0.027
Absorption correction: multi-scan (SADABS; Bruker, 2001)	θmax = 28.3°, θmin = 1.5°
Tmin = 0.93, Tmax = 0.98	h = −9→9
18036 measured reflections	k = −12→11
2053 independent reflections	l = −35→35

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.135	w = 1/[σ^2(Fo^2) + (0.0604P)^2 + 0.6359P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.001
2053 reflections	Δρmax = 0.24 e Å^−3
132 parameters	Δρmin = −0.24 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
C2	−0.07636 (19)	0.32869 (16)	0.47064 (5)	0.0316 (3)
C4	0.1030 (2)	0.49840 (16)	0.41648 (5)	0.0325 (3)
C5	−0.0782 (2)	0.54865 (18)	0.39597 (6)	0.0375 (4)
C6	−0.2403 (2)	0.49198 (18)	0.41510 (6)	0.0390 (4)
H6	−0.3578	0.5258	0.4030	0.047*
C9	−0.0753 (3)	0.6606 (2)	0.35470 (8)	0.0594 (5)
H9A	−0.2047	0.6891	0.3467	0.089*
H9B	−0.0152	0.6181	0.3258	0.089*
H9C	−0.0040	0.7462	0.3652	0.089*
N1	−0.24038 (19)	0.38586 (15)	0.45190 (5)	0.0377 (3)
H1N	−0.346 (3)	0.354 (2)	0.4646 (7)	0.048 (5)*
N3	0.08942 (17)	0.38759 (14)	0.45211 (5)	0.0331 (3)
H2N	0.195 (3)	0.355 (2)	0.4653 (7)	0.041 (5)*
O7	−0.07500 (14)	0.23058 (13)	0.50296 (4)	0.0413 (3)
O8	0.26309 (15)	0.54574 (14)	0.40549 (4)	0.0425 (3)
C10	0.5000	0.7480 (2)	0.2500	0.0400 (5)
H10	0.5000	0.8510	0.2500	0.048*
C11	0.4423 (2)	0.67069 (18)	0.29187 (6)	0.0372 (4)
C12	0.4383 (3)	0.51775 (19)	0.29181 (7)	0.0509 (5)
H12	0.3946	0.4659	0.3195	0.061*
C13	0.5000	0.4434 (3)	0.2500	0.0655 (8)
H13	0.5000	0.3403	0.2500	0.079*
O14	0.3922 (2)	0.74992 (15)	0.33346 (5)	0.0522 (4)
H1O	0.346 (4)	0.687 (3)	0.3553 (9)	0.075 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0256 (7)	0.0362 (7)	0.0331 (7)	−0.0012 (5)	0.0001 (5)	0.0023 (6)
C4	0.0305 (7)	0.0362 (7)	0.0309 (7)	−0.0003 (5)	0.0034 (5)	0.0014 (6)
C5	0.0349 (8)	0.0377 (8)	0.0399 (8)	0.0014 (6)	−0.0008 (6)	0.0062 (6)
C6	0.0296 (7)	0.0413 (8)	0.0461 (8)	0.0033 (6)	−0.0066 (6)	0.0065 (7)
C9	0.0467 (10)	0.0650 (12)	0.0665 (12)	0.0041 (9)	−0.0016 (9)	0.0327 (10)
N1	0.0233 (6)	0.0433 (7)	0.0464 (7)	−0.0022 (5)	0.0002 (5)	0.0097 (6)
N3	0.0226 (6)	0.0407 (7)	0.0359 (6)	0.0013 (5)	−0.0003 (5)	0.0068 (5)
O7	0.0265 (5)	0.0512 (7)	0.0463 (6)	−0.0010 (4)	0.0008 (4)	0.0178 (5)
O8	0.0312 (5)	0.0527 (7)	0.0436 (6)	−0.0047 (5)	0.0053 (4)	0.0108 (5)
C10	0.0448 (12)	0.0300 (10)	0.0453 (12)	0.000	0.0090 (10)	0.000
C11	0.0355 (8)	0.0387 (8)	0.0375 (8)	0.0010 (6)	0.0032 (6)	−0.0026 (6)
C12	0.0727 (12)	0.0378 (9)	0.0423 (9)	−0.0026 (8)	0.0095 (8)	0.0070 (7)
C13	0.110 (3)	0.0313 (12)	0.0550 (15)	0.000	0.0145 (16)	0.000
O14	0.0689 (9)	0.0438 (7)	0.0440 (7)	−0.0018 (6)	0.0195 (6)	−0.0037 (5)

Geometric parameters (Å, º)

C2—O7	1.2393 (18)	N1—H1N	0.86 (2)
C2—N1	1.3485 (18)	N3—H2N	0.86 (2)
C2—N3	1.3627 (18)	C10—C11^i	1.3817 (19)
C4—O8	1.2276 (17)	C10—C11	1.3818 (19)
C4—N3	1.3867 (19)	C10—H10	0.9300
C4—C5	1.447 (2)	C11—O14	1.3701 (19)
C5—C6	1.340 (2)	C11—C12	1.380 (2)
C5—C9	1.499 (2)	C12—C13	1.376 (2)
C6—N1	1.375 (2)	C12—H12	0.9300
C6—H6	0.9300	C13—C12^i	1.376 (2)
C9—H9A	0.9600	C13—H13	0.9300
C9—H9B	0.9600	O14—H1O	0.88 (3)
C9—H9C	0.9600
O7—C2—N1	122.73 (13)	C2—N1—H1N	116.5 (13)
O7—C2—N3	121.83 (13)	C6—N1—H1N	121.2 (13)
N1—C2—N3	115.44 (13)	C2—N3—C4	126.18 (12)
O8—C4—N3	118.57 (13)	C2—N3—H2N	116.0 (12)
O8—C4—C5	126.03 (13)	C4—N3—H2N	117.7 (12)
N3—C4—C5	115.39 (12)	C11^i—C10—C11	119.4 (2)
C6—C5—C4	117.83 (14)	C11^i—C10—H10	120.3
C6—C5—C9	123.46 (14)	C11—C10—H10	120.3
C4—C5—C9	118.71 (13)	O14—C11—C12	121.17 (15)
C5—C6—N1	122.74 (13)	O14—C11—C10	118.19 (15)
C5—C6—H6	118.6	C12—C11—C10	120.63 (15)
N1—C6—H6	118.6	C13—C12—C11	118.84 (17)
C5—C9—H9A	109.5	C13—C12—H12	120.6
C5—C9—H9B	109.5	C11—C12—H12	120.6
H9A—C9—H9B	109.5	C12^i—C13—C12	121.6 (2)
C5—C9—H9C	109.5	C12^i—C13—H13	119.2
H9A—C9—H9C	109.5	C12—C13—H13	119.2
H9B—C9—H9C	109.5	C11—O14—H1O	107.5 (17)
C2—N1—C6	122.26 (13)
O8—C4—C5—C6	−175.07 (16)	O7—C2—N3—C4	−179.22 (14)
N3—C4—C5—C6	4.2 (2)	N1—C2—N3—C4	−0.1 (2)
O8—C4—C5—C9	4.9 (3)	O8—C4—N3—C2	176.05 (14)
N3—C4—C5—C9	−175.78 (16)	C5—C4—N3—C2	−3.3 (2)
C4—C5—C6—N1	−2.1 (2)	C11^i—C10—C11—O14	177.76 (16)
C9—C5—C6—N1	177.90 (18)	C11^i—C10—C11—C12	−1.30 (12)
O7—C2—N1—C6	−178.27 (15)	O14—C11—C12—C13	−176.48 (14)
N3—C2—N1—C6	2.6 (2)	C10—C11—C12—C13	2.6 (2)
C5—C6—N1—C2	−1.5 (3)	C11—C12—C13—C12^i	−1.26 (12)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O7^ii	0.86 (2)	1.97 (2)	2.8247 (17)	175 (2)
N3—H2N···O7^iii	0.86 (2)	1.97 (2)	2.8336 (16)	176 (2)
O14—H1O···O8	0.88 (3)	1.94 (3)	2.8167 (17)	175 (2)

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

(III) 5-Methylpyrimidine-2,4(1H,3H)-dione–benzene-1,4-diol (2/1)

Crystal data

2C5H6N2O2·C6H6O2	F(000) = 380
Mr = 362.34	Dx = 1.453 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.204 (3) Å	Cell parameters from 5536 reflections
b = 6.9634 (13) Å	θ = 2.9–28.3°
c = 8.4505 (15) Å	µ = 0.11 mm^−1
β = 97.639 (3)°	T = 294 K
V = 828.4 (3) Å^3	Block, colourless
Z = 2	0.19 × 0.17 × 0.11 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	1795 reflections with I > 2σ(I)
ω scans	Rint = 0.016
Absorption correction: multi-scan (SADABS; Bruker, 2001)	θmax = 28.3°, θmin = 2.9°
Tmin = 0.95, Tmax = 0.99	h = −18→18
9216 measured reflections	k = −8→9
1993 independent reflections	l = −11→11

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.123	w = 1/[σ^2(Fo^2) + (0.0761P)^2 + 0.1217P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1993 reflections	Δρmax = 0.30 e Å^−3
131 parameters	Δρmin = −0.16 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
C2	0.05890 (8)	0.07119 (14)	0.68305 (13)	0.0326 (2)
C4	0.16775 (7)	−0.11392 (15)	0.54085 (13)	0.0333 (2)
C5	0.20629 (8)	0.06465 (15)	0.48908 (14)	0.0357 (3)
C6	0.16838 (8)	0.22928 (16)	0.53445 (13)	0.0368 (3)
H6	0.1917	0.3451	0.5011	0.044*
C9	0.28532 (10)	0.05661 (18)	0.38818 (19)	0.0506 (3)
H9A	0.3000	0.1842	0.3561	0.076*
H9B	0.2661	−0.0202	0.2951	0.076*
H9C	0.3405	0.0006	0.4486	0.076*
N1	0.09611 (7)	0.23300 (13)	0.62866 (11)	0.0368 (2)
H1N	0.0699 (10)	−0.201 (2)	0.6705 (18)	0.050 (4)*
N3	0.09643 (6)	−0.09626 (12)	0.63644 (11)	0.0339 (2)
H2N	0.0694 (10)	0.340 (2)	0.6545 (18)	0.047 (4)*
O7	−0.00587 (6)	0.07241 (10)	0.76821 (11)	0.0417 (2)
O8	0.19223 (6)	−0.27636 (11)	0.50584 (11)	0.0452 (2)
C10	0.40986 (8)	−0.46666 (16)	0.41857 (14)	0.0394 (3)
C11	0.43502 (8)	−0.39291 (17)	0.57083 (14)	0.0432 (3)
H11	0.3914	−0.3210	0.6187	0.052*
C12	0.52483 (9)	−0.42616 (17)	0.65162 (16)	0.0455 (3)
H12	0.5414	−0.3762	0.7536	0.055*
O13	0.32155 (7)	−0.43836 (14)	0.33328 (12)	0.0513 (3)
H3O	0.2831 (14)	−0.376 (3)	0.393 (2)	0.074 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0362 (5)	0.0249 (5)	0.0370 (5)	0.0006 (3)	0.0054 (4)	−0.0011 (3)
C4	0.0335 (5)	0.0285 (5)	0.0381 (5)	0.0019 (4)	0.0054 (4)	−0.0001 (4)
C5	0.0371 (5)	0.0317 (5)	0.0388 (5)	−0.0020 (4)	0.0067 (4)	0.0027 (4)
C6	0.0426 (6)	0.0280 (5)	0.0404 (5)	−0.0052 (4)	0.0072 (4)	0.0021 (4)
C9	0.0514 (7)	0.0412 (6)	0.0638 (8)	−0.0004 (5)	0.0252 (6)	0.0059 (5)
N1	0.0447 (5)	0.0219 (4)	0.0451 (5)	0.0004 (3)	0.0110 (4)	−0.0015 (3)
N3	0.0384 (5)	0.0216 (4)	0.0433 (5)	−0.0003 (3)	0.0105 (4)	0.0007 (3)
O7	0.0467 (5)	0.0267 (4)	0.0556 (5)	0.0012 (3)	0.0211 (4)	−0.0011 (3)
O8	0.0476 (5)	0.0294 (4)	0.0617 (5)	0.0043 (3)	0.0193 (4)	−0.0024 (3)
C10	0.0383 (6)	0.0342 (5)	0.0473 (6)	0.0009 (4)	0.0117 (4)	0.0013 (4)
C11	0.0430 (6)	0.0410 (6)	0.0487 (7)	0.0067 (5)	0.0172 (5)	−0.0043 (5)
C12	0.0475 (7)	0.0466 (7)	0.0437 (6)	0.0037 (5)	0.0115 (5)	−0.0074 (5)
O13	0.0431 (5)	0.0542 (6)	0.0565 (6)	0.0096 (4)	0.0061 (4)	−0.0078 (4)

Geometric parameters (Å, º)

C2—O7	1.2412 (13)	C9—H9C	0.9600
C2—N1	1.3509 (13)	N1—H2N	0.879 (16)
C2—N3	1.3619 (13)	N3—H1N	0.886 (17)
C4—O8	1.2310 (13)	C10—O13	1.3753 (15)
C4—N3	1.3825 (14)	C10—C12^i	1.3841 (16)
C4—C5	1.4495 (14)	C10—C11	1.3873 (18)
C5—C6	1.3439 (15)	C11—C12	1.3839 (17)
C5—C9	1.4983 (16)	C11—H11	0.9300
C6—N1	1.3805 (14)	C12—C10^i	1.3841 (16)
C6—H6	0.9300	C12—H12	0.9300
C9—H9A	0.9600	O13—H3O	0.91 (2)
C9—H9B	0.9600
O7—C2—N1	123.04 (9)	H9B—C9—H9C	109.5
O7—C2—N3	121.50 (9)	C2—N1—C6	122.36 (9)
N1—C2—N3	115.46 (10)	C2—N1—H2N	115.1 (10)
O8—C4—N3	118.33 (9)	C6—N1—H2N	122.5 (10)
O8—C4—C5	125.85 (10)	C2—N3—C4	126.19 (9)
N3—C4—C5	115.82 (9)	C2—N3—H1N	114.3 (9)
C6—C5—C4	117.64 (10)	C4—N3—H1N	119.5 (9)
C6—C5—C9	123.59 (10)	O13—C10—C12^i	117.99 (11)
C4—C5—C9	118.78 (10)	O13—C10—C11	122.52 (10)
C5—C6—N1	122.51 (9)	C12^i—C10—C11	119.49 (11)
C5—C6—H6	118.7	C12—C11—C10	120.17 (11)
N1—C6—H6	118.7	C12—C11—H11	119.9
C5—C9—H9A	109.5	C10—C11—H11	119.9
C5—C9—H9B	109.5	C11—C12—C10^i	120.34 (12)
H9A—C9—H9B	109.5	C11—C12—H12	119.8
C5—C9—H9C	109.5	C10^i—C12—H12	119.8
H9A—C9—H9C	109.5	C10—O13—H3O	110.5 (12)
O8—C4—C5—C6	177.60 (11)	C5—C6—N1—C2	0.56 (18)
N3—C4—C5—C6	−1.58 (16)	O7—C2—N3—C4	179.34 (10)
O8—C4—C5—C9	−2.16 (19)	N1—C2—N3—C4	0.15 (17)
N3—C4—C5—C9	178.65 (10)	O8—C4—N3—C2	−178.10 (10)
C4—C5—C6—N1	0.82 (17)	C5—C4—N3—C2	1.15 (17)
C9—C5—C6—N1	−179.42 (11)	O13—C10—C11—C12	179.81 (11)
O7—C2—N1—C6	179.78 (10)	C12^i—C10—C11—C12	0.1 (2)
N3—C2—N1—C6	−1.05 (16)	C10—C11—C12—C10^i	−0.1 (2)

Symmetry code: (i) −x+1, −y−1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2N···O7^ii	0.879 (16)	2.002 (17)	2.8784 (12)	174.6 (14)
N3—H1N···O7^iii	0.886 (17)	1.926 (17)	2.8111 (12)	176.1 (14)
O13—H3O···O8	0.91 (2)	1.84 (2)	2.7359 (13)	171.6 (18)

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

(IV) 5-Methylpyrimidine-2,4(1H,3H)-dione–benzene-1,2,3-triol (1/2)

Crystal data

C5H6N2O2·2C6H6O3	Z = 2
Mr = 378.33	F(000) = 396
Triclinic, P1	Dx = 1.484 Mg m^−3
a = 6.9652 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2125 (19) Å	Cell parameters from 5658 reflections
c = 12.951 (2) Å	θ = 2.9–28.0°
α = 97.218 (3)°	µ = 0.12 mm^−1
β = 99.189 (3)°	T = 294 K
γ = 108.549 (3)°	Plate, colourless
V = 846.7 (3) Å^3	0.17 × 0.06 × 0.05 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3295 reflections with I > 2σ(I)
ω scans	Rint = 0.026
Absorption correction: multi-scan (SADABS; Bruker, 2001)	θmax = 28.1°, θmin = 1.6°
Tmin = 0.93, Tmax = 0.97	h = −9→9
9492 measured reflections	k = −13→13
3876 independent reflections	l = −16→17

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.131	w = 1/[σ^2(Fo^2) + (0.0811P)^2 + 0.1267P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3876 reflections	Δρmax = 0.40 e Å^−3
277 parameters	Δρmin = −0.21 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
C2	0.3691 (2)	0.78633 (13)	0.46045 (10)	0.0347 (3)
C4	0.33483 (19)	0.79165 (13)	0.26989 (10)	0.0318 (3)
C5	0.24976 (19)	0.63993 (13)	0.24749 (10)	0.0344 (3)
C6	0.2361 (2)	0.57387 (14)	0.33104 (11)	0.0389 (3)
H6	0.1848	0.4761	0.3179	0.047*
C9	0.1803 (2)	0.56287 (15)	0.13386 (11)	0.0437 (3)
H9A	0.1270	0.4635	0.1323	0.065*
H9B	0.2959	0.5844	0.0994	0.065*
H9C	0.0738	0.5916	0.0973	0.065*
N1	0.2946 (2)	0.64448 (12)	0.43483 (9)	0.0400 (3)
H1N	0.297 (3)	0.602 (2)	0.4876 (16)	0.056 (5)*
N3	0.38754 (18)	0.85454 (11)	0.37635 (8)	0.0349 (3)
H2N	0.443 (3)	0.951 (2)	0.3935 (14)	0.051 (5)*
O7	0.41733 (18)	0.85216 (10)	0.55386 (7)	0.0448 (3)
O8	0.36205 (16)	0.86785 (10)	0.20225 (7)	0.0415 (2)
C10A	0.0768 (2)	0.84928 (13)	0.75311 (10)	0.0338 (3)
C11A	0.24804 (18)	0.84800 (12)	0.82449 (9)	0.0304 (3)
C12A	0.2351 (2)	0.83645 (13)	0.92954 (10)	0.0335 (3)
C13A	0.0518 (2)	0.83135 (14)	0.96268 (11)	0.0397 (3)
H13A	0.0425	0.8258	1.0329	0.048*
C14A	−0.1163 (2)	0.83453 (16)	0.89047 (12)	0.0437 (3)
H14A	−0.2376	0.8315	0.9131	0.052*
C15A	−0.1064 (2)	0.84208 (15)	0.78540 (12)	0.0415 (3)
H15A	−0.2206	0.8423	0.7372	0.050*
O16A	0.08891 (17)	0.86224 (11)	0.64914 (7)	0.0415 (2)
H1O	0.205 (4)	0.852 (2)	0.6359 (17)	0.069 (6)*
O17A	0.42668 (14)	0.85211 (10)	0.78862 (7)	0.0353 (2)
H2O	0.504 (3)	0.942 (2)	0.7919 (14)	0.049 (5)*
O18A	0.40493 (16)	0.83019 (12)	0.99403 (8)	0.0452 (3)
H3O	0.389 (3)	0.833 (2)	1.0608 (16)	0.055 (5)*
C10B	0.2995 (2)	0.48722 (14)	0.69600 (11)	0.0370 (3)
C11B	0.2169 (2)	0.36068 (14)	0.62317 (10)	0.0357 (3)
C12B	0.1639 (2)	0.23452 (14)	0.66014 (11)	0.0385 (3)
C13B	0.1944 (2)	0.23437 (15)	0.76864 (12)	0.0433 (3)
H13B	0.1599	0.1499	0.7932	0.052*
C14B	0.2767 (2)	0.36140 (16)	0.84004 (11)	0.0434 (3)
H14B	0.2970	0.3615	0.9128	0.052*
C15B	0.3291 (2)	0.48821 (15)	0.80470 (11)	0.0407 (3)
H15B	0.3835	0.5729	0.8532	0.049*
O16B	0.3469 (2)	0.60497 (11)	0.65181 (9)	0.0547 (3)
H4O	0.390 (3)	0.674 (2)	0.6982 (17)	0.060 (6)*
O17B	0.19057 (19)	0.36604 (12)	0.51664 (8)	0.0487 (3)
H5O	0.127 (4)	0.287 (3)	0.4805 (19)	0.076 (7)*
O18B	0.0806 (2)	0.11680 (11)	0.58150 (9)	0.0582 (3)
H6O	0.070 (3)	0.047 (3)	0.6076 (17)	0.070 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0429 (6)	0.0343 (6)	0.0263 (6)	0.0104 (5)	0.0109 (5)	0.0076 (5)
C4	0.0346 (6)	0.0351 (6)	0.0259 (6)	0.0112 (5)	0.0087 (4)	0.0059 (5)
C5	0.0365 (6)	0.0339 (6)	0.0307 (6)	0.0106 (5)	0.0072 (5)	0.0029 (5)
C6	0.0483 (7)	0.0297 (6)	0.0351 (7)	0.0096 (5)	0.0079 (5)	0.0039 (5)
C9	0.0517 (8)	0.0405 (7)	0.0331 (7)	0.0131 (6)	0.0058 (6)	−0.0014 (5)
N1	0.0558 (7)	0.0331 (6)	0.0297 (6)	0.0111 (5)	0.0108 (5)	0.0098 (4)
N3	0.0470 (6)	0.0293 (5)	0.0262 (5)	0.0083 (5)	0.0109 (4)	0.0056 (4)
O7	0.0665 (7)	0.0371 (5)	0.0259 (5)	0.0099 (5)	0.0130 (4)	0.0057 (4)
O8	0.0551 (6)	0.0395 (5)	0.0281 (5)	0.0116 (4)	0.0120 (4)	0.0091 (4)
C10A	0.0403 (6)	0.0303 (6)	0.0300 (6)	0.0111 (5)	0.0070 (5)	0.0063 (4)
C11A	0.0339 (6)	0.0281 (5)	0.0288 (6)	0.0090 (4)	0.0093 (5)	0.0051 (4)
C12A	0.0392 (6)	0.0331 (6)	0.0274 (6)	0.0108 (5)	0.0080 (5)	0.0057 (4)
C13A	0.0471 (7)	0.0424 (7)	0.0325 (6)	0.0150 (6)	0.0167 (5)	0.0081 (5)
C14A	0.0398 (7)	0.0471 (8)	0.0489 (8)	0.0163 (6)	0.0187 (6)	0.0107 (6)
C15A	0.0371 (7)	0.0452 (7)	0.0432 (8)	0.0162 (6)	0.0059 (6)	0.0097 (6)
O16A	0.0491 (6)	0.0497 (6)	0.0282 (5)	0.0194 (5)	0.0068 (4)	0.0117 (4)
O17A	0.0372 (5)	0.0373 (5)	0.0328 (5)	0.0119 (4)	0.0136 (4)	0.0069 (4)
O18A	0.0465 (6)	0.0649 (7)	0.0277 (5)	0.0226 (5)	0.0081 (4)	0.0124 (4)
C10B	0.0422 (7)	0.0334 (6)	0.0354 (7)	0.0118 (5)	0.0092 (5)	0.0090 (5)
C11B	0.0403 (6)	0.0361 (6)	0.0316 (6)	0.0139 (5)	0.0076 (5)	0.0079 (5)
C12B	0.0431 (7)	0.0336 (6)	0.0378 (7)	0.0123 (5)	0.0066 (5)	0.0079 (5)
C13B	0.0518 (8)	0.0385 (7)	0.0409 (8)	0.0140 (6)	0.0110 (6)	0.0157 (6)
C14B	0.0500 (8)	0.0500 (8)	0.0314 (7)	0.0171 (6)	0.0100 (6)	0.0112 (6)
C15B	0.0461 (7)	0.0407 (7)	0.0330 (7)	0.0135 (6)	0.0073 (5)	0.0039 (5)
O16B	0.0888 (9)	0.0311 (5)	0.0366 (6)	0.0111 (5)	0.0111 (6)	0.0076 (4)
O17B	0.0716 (7)	0.0369 (5)	0.0312 (5)	0.0121 (5)	0.0060 (5)	0.0075 (4)
O18B	0.0927 (9)	0.0308 (5)	0.0408 (6)	0.0134 (6)	0.0014 (6)	0.0069 (4)

Geometric parameters (Å, º)

C2—O7	1.2452 (16)	C13A—H13A	0.9300
C2—N1	1.3505 (17)	C14A—C15A	1.384 (2)
C2—N3	1.3663 (16)	C14A—H14A	0.9300
C4—O8	1.2407 (15)	C15A—H15A	0.9300
C4—N3	1.3836 (16)	O16A—H1O	0.89 (2)
C4—C5	1.4436 (18)	O17A—H2O	0.90 (2)
C5—C6	1.3456 (19)	O18A—H3O	0.89 (2)
C5—C9	1.5028 (18)	C10B—O16B	1.3650 (17)
C6—N1	1.3739 (17)	C10B—C15B	1.3881 (19)
C6—H6	0.9300	C10B—C11B	1.3922 (19)
C9—H9A	0.9600	C11B—O17B	1.3729 (16)
C9—H9B	0.9600	C11B—C12B	1.3908 (19)
C9—H9C	0.9600	C12B—O18B	1.3708 (17)
N1—H1N	0.85 (2)	C12B—C13B	1.388 (2)
N3—H2N	0.92 (2)	C13B—C14B	1.387 (2)
C10A—O16A	1.3827 (16)	C13B—H13B	0.9300
C10A—C15A	1.388 (2)	C14B—C15B	1.386 (2)
C10A—C11A	1.3921 (18)	C14B—H14B	0.9300
C11A—O17A	1.3864 (15)	C15B—H15B	0.9300
C11A—C12A	1.3951 (17)	O16B—H4O	0.81 (2)
C12A—O18A	1.3592 (16)	O17B—H5O	0.83 (3)
C12A—C13A	1.3982 (19)	O18B—H6O	0.82 (2)
C13A—C14A	1.389 (2)
O7—C2—N1	123.07 (12)	C14A—C13A—C12A	119.87 (12)
O7—C2—N3	121.49 (12)	C14A—C13A—H13A	120.1
N1—C2—N3	115.45 (11)	C12A—C13A—H13A	120.1
O8—C4—N3	118.63 (11)	C15A—C14A—C13A	121.10 (13)
O8—C4—C5	125.50 (12)	C15A—C14A—H14A	119.4
N3—C4—C5	115.87 (11)	C13A—C14A—H14A	119.4
C6—C5—C4	117.53 (11)	C14A—C15A—C10A	118.89 (13)
C6—C5—C9	122.94 (12)	C14A—C15A—H15A	120.6
C4—C5—C9	119.53 (12)	C10A—C15A—H15A	120.6
C5—C6—N1	122.91 (12)	C10A—O16A—H1O	109.7 (14)
C5—C6—H6	118.5	C11A—O17A—H2O	108.6 (11)
N1—C6—H6	118.5	C12A—O18A—H3O	110.7 (12)
C5—C9—H9A	109.5	O16B—C10B—C15B	124.48 (13)
C5—C9—H9B	109.5	O16B—C10B—C11B	114.95 (12)
H9A—C9—H9B	109.5	C15B—C10B—C11B	120.57 (12)
C5—C9—H9C	109.5	O17B—C11B—C12B	122.51 (12)
H9A—C9—H9C	109.5	O17B—C11B—C10B	118.05 (12)
H9B—C9—H9C	109.5	C12B—C11B—C10B	119.44 (12)
C2—N1—C6	122.16 (12)	O18B—C12B—C13B	125.14 (13)
C2—N1—H1N	115.2 (14)	O18B—C12B—C11B	114.43 (13)
C6—N1—H1N	122.4 (14)	C13B—C12B—C11B	120.43 (13)
C2—N3—C4	126.04 (11)	C14B—C13B—C12B	119.35 (13)
C2—N3—H2N	115.8 (11)	C14B—C13B—H13B	120.3
C4—N3—H2N	118.2 (11)	C12B—C13B—H13B	120.3
O16A—C10A—C15A	118.78 (12)	C15B—C14B—C13B	121.05 (13)
O16A—C10A—C11A	120.24 (12)	C15B—C14B—H14B	119.5
C15A—C10A—C11A	120.95 (12)	C13B—C14B—H14B	119.5
O17A—C11A—C10A	119.23 (11)	C14B—C15B—C10B	119.16 (13)
O17A—C11A—C12A	120.88 (11)	C14B—C15B—H15B	120.4
C10A—C11A—C12A	119.83 (11)	C10B—C15B—H15B	120.4
O18A—C12A—C11A	116.90 (11)	C10B—O16B—H4O	109.6 (14)
O18A—C12A—C13A	123.79 (12)	C11B—O17B—H5O	110.4 (16)
C11A—C12A—C13A	119.31 (12)	C12B—O18B—H6O	109.7 (16)
O8—C4—C5—C6	178.31 (13)	O18A—C12A—C13A—C14A	−178.23 (13)
N3—C4—C5—C6	−2.22 (18)	C11A—C12A—C13A—C14A	1.5 (2)
O8—C4—C5—C9	−1.9 (2)	C12A—C13A—C14A—C15A	0.3 (2)
N3—C4—C5—C9	177.60 (12)	C13A—C14A—C15A—C10A	−1.3 (2)
C4—C5—C6—N1	1.6 (2)	O16A—C10A—C15A—C14A	−177.56 (13)
C9—C5—C6—N1	−178.25 (13)	C11A—C10A—C15A—C14A	0.4 (2)
O7—C2—N1—C6	177.90 (13)	O16B—C10B—C11B—O17B	−0.37 (19)
N3—C2—N1—C6	−1.7 (2)	C15B—C10B—C11B—O17B	179.85 (13)
C5—C6—N1—C2	0.5 (2)	O16B—C10B—C11B—C12B	179.83 (13)
O7—C2—N3—C4	−178.71 (13)	C15B—C10B—C11B—C12B	0.0 (2)
N1—C2—N3—C4	0.9 (2)	O17B—C11B—C12B—O18B	−1.0 (2)
O8—C4—N3—C2	−179.45 (12)	C10B—C11B—C12B—O18B	178.84 (13)
C5—C4—N3—C2	1.05 (19)	O17B—C11B—C12B—C13B	179.69 (13)
O16A—C10A—C11A—O17A	−3.50 (18)	C10B—C11B—C12B—C13B	−0.5 (2)
C15A—C10A—C11A—O17A	178.53 (12)	O18B—C12B—C13B—C14B	−178.74 (15)
O16A—C10A—C11A—C12A	179.29 (11)	C11B—C12B—C13B—C14B	0.5 (2)
C15A—C10A—C11A—C12A	1.32 (19)	C12B—C13B—C14B—C15B	−0.1 (2)
O17A—C11A—C12A—O18A	0.30 (18)	C13B—C14B—C15B—C10B	−0.4 (2)
C10A—C11A—C12A—O18A	177.46 (11)	O16B—C10B—C15B—C14B	−179.37 (14)
O17A—C11A—C12A—C13A	−179.43 (11)	C11B—C10B—C15B—C14B	0.4 (2)
C10A—C11A—C12A—C13A	−2.27 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O16B	0.85 (2)	2.09 (2)	2.8713 (17)	151 (2)
N1—H1N···O17B	0.85 (2)	2.38 (2)	3.0701 (16)	138 (2)
N3—H2N···O7^i	0.92 (2)	1.91 (2)	2.8237 (16)	172 (2)
O16A—H1O···O7	0.89 (2)	1.95 (2)	2.7903 (16)	156 (2)
O16A—H1O···O17A	0.89 (2)	2.31 (2)	2.7665 (14)	112 (2)
O17A—H2O···O8^i	0.90 (2)	1.85 (2)	2.7460 (15)	174 (2)
O18A—H3O···O8^ii	0.89 (2)	1.87 (2)	2.7530 (14)	172 (2)
O16B—H4O···O17A	0.81 (2)	1.96 (2)	2.7364 (15)	163 (2)
O17B—H5O···O16A^iii	0.83 (3)	2.12 (3)	2.8904 (15)	155 (2)
O17B—H5O···O18B	0.83 (3)	2.27 (2)	2.6970 (16)	112 (2)
O18B—H6O···O16A^iv	0.82 (2)	2.06 (2)	2.8602 (16)	166 (2)

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