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.
Supporting information
CCDC references: 1406963; 1406962; 1406961; 1406960
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(1
H,3
H)-dione–benzene-1,2-diol (1/1)
top
Crystal data top
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) Å3 | Block, colourless |
Z = 8 | 0.18 × 0.15 × 0.08 mm |
F(000) = 992 | |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.134 | w = 1/[σ2(Fo2) + (0.0581P)2 + 0.5148P] where P = (Fo2 + 2Fc2)/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 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O7i | 0.871 (19) | 1.973 (19) | 2.842 (2) | 176 (2) |
N3—H2N···O7ii | 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···O16iii | 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(1
H,3
H)-dione–benzene-1,3-diol (2/1)
top
Crystal data top
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) Å3 | Needle, colourless |
Z = 4 | 0.18 × 0.11 × 0.09 mm |
F(000) = 760 | |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.135 | w = 1/[σ2(Fo2) + (0.0604P)2 + 0.6359P] where P = (Fo2 + 2Fc2)/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 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C11i | 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—C12i | 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) | C11i—C10—C11 | 119.4 (2) |
C6—C5—C4 | 117.83 (14) | C11i—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 | C12i—C13—C12 | 121.6 (2) |
C5—C9—H9C | 109.5 | C12i—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) | C11i—C10—C11—O14 | 177.76 (16) |
C9—C5—C6—N1 | 177.90 (18) | C11i—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—C12i | −1.26 (12) |
Symmetry code: (i) −x+1, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O7ii | 0.86 (2) | 1.97 (2) | 2.8247 (17) | 175 (2) |
N3—H2N···O7iii | 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(1
H,3
H)-dione–benzene-1,4-diol (2/1)
top
Crystal data top
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) Å3 | Block, colourless |
Z = 2 | 0.19 × 0.17 × 0.11 mm |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.0761P)2 + 0.1217P] where P = (Fo2 + 2Fc2)/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 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C12i | 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—C10i | 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—C12i | 117.99 (11) |
C4—C5—C9 | 118.78 (10) | O13—C10—C11 | 122.52 (10) |
C5—C6—N1 | 122.51 (9) | C12i—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—C10i | 120.34 (12) |
H9A—C9—H9B | 109.5 | C11—C12—H12 | 119.8 |
C5—C9—H9C | 109.5 | C10i—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) | C12i—C10—C11—C12 | 0.1 (2) |
N3—C2—N1—C6 | −1.05 (16) | C10—C11—C12—C10i | −0.1 (2) |
Symmetry code: (i) −x+1, −y−1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H2N···O7ii | 0.879 (16) | 2.002 (17) | 2.8784 (12) | 174.6 (14) |
N3—H1N···O7iii | 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(1
H,3
H)-dione–benzene-1,2,3-triol (1/2)
top
Crystal data top
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) Å3 | 0.17 × 0.06 × 0.05 mm |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.131 | w = 1/[σ2(Fo2) + (0.0811P)2 + 0.1267P] where P = (Fo2 + 2Fc2)/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 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···O7i | 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···O8i | 0.90 (2) | 1.85 (2) | 2.7460 (15) | 174 (2) |
O18A—H3O···O8ii | 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···O16Aiii | 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···O16Aiv | 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. |