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In the title cocrystal, trimethoprim maleate [2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidin-1-ium maleate], C
14H
19N
4O
3+·C
4H
3O
4−, 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.
Supporting information
CCDC reference: 163930
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.
Crystal data top
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) Å3 | 0.31 × 0.26 × 0.17 mm |
Z = 4 | |
Data collection top
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 top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.1407P)2] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.065 | (Δ/σ)max < 0.001 |
wR(F2) = 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+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
278 parameters | Extinction coefficient: 0.0017 (5) |
0 restraints | |
Special details top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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···C10i | 3.352 (8) | C6'···H10C | 2.6945 |
O1···C10ii | 3.355 (8) | C6'···H10B | 2.7785 |
O2···O3 | 2.674 (6) | C6'···H6v | 3.0419 |
O2···O1 | 2.669 (5) | C7···H4B | 2.5441 |
O3···C9 | 3.249 (7) | C8···H10Cii | 3.0607 |
O3···O2 | 2.674 (6) | C8···H2' | 2.5500 |
O3···C8iii | 3.329 (8) | C9···H8Aiii | 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···C2iv | 3.324 (6) | C14···H4 | 2.13 (6) |
O6···C11 | 3.094 (7) | C14···H8Cvii | 3.0831 |
O6···C13v | 3.344 (7) | C14···H2Bvi | 2.7597 |
O6···O4 | 2.423 (6) | H1···O5 | 1.8998 |
O6···N2vi | 3.113 (6) | H1···C11 | 2.6224 |
O7···N4vii | 2.829 (6) | H1···O4 | 2.6931 |
O7···N2vi | 3.041 (6) | H1···H2A | 2.2629 |
O1···H10Cii | 2.5893 | H2'···C8 | 2.5500 |
O1···H9A | 2.8863 | H2'···H7B | 2.3882 |
O1···H10Ai | 2.6674 | H2'···H8C | 2.4545 |
O2···H10Ai | 2.7129 | H2'···H8B | 2.2552 |
O2···H8Aiii | 2.6001 | H2A···C11 | 3.0165 |
O3···H9C | 2.8297 | H2A···H1 | 2.2629 |
O3···H8Aiii | 2.6065 | H2A···O4 | 2.1326 |
O3···H8Bviii | 2.8700 | H2B···O6vi | 2.6415 |
O4···H1 | 2.6931 | H2B···O7vi | 2.1991 |
O4···H12v | 2.7346 | H2B···C14vi | 2.7597 |
O4···H2A | 2.1326 | H4···O6 | 1.36 (6) |
O5···H1 | 1.8998 | H4···C13 | 2.42 (6) |
O6···H13v | 2.6182 | H4···C14 | 2.13 (6) |
O6···H4 | 1.36 (6) | H4A···N3ix | 2.1306 |
O6···H2Bvi | 2.6415 | H4A···C2ix | 3.0891 |
O7···H4Bvii | 2.1365 | H4A···C4ix | 3.0141 |
O7···H2Bvi | 2.1991 | H4A···H4Aix | 2.5077 |
N1···O5 | 2.747 (6) | H4B···O7xi | 2.1365 |
N2···O4 | 2.936 (6) | H4B···C1' | 2.7991 |
N2···O6vi | 3.113 (6) | H4B···C7 | 2.5441 |
N2···O7vi | 3.041 (6) | H4B···H7B | 2.2138 |
N3···N4ix | 2.985 (5) | H6···C6'iv | 3.0419 |
N3···C4x | 3.436 (6) | H6···H7A | 2.3860 |
N4···O7xi | 2.829 (6) | H6'···C5 | 2.6416 |
N4···C1' | 3.256 (5) | H6'···C6 | 2.9612 |
N4···C6v | 3.357 (6) | H6'···C10 | 2.5180 |
N4···N3ix | 2.985 (5) | H6'···H10C | 2.2118 |
N4···C2x | 3.414 (6) | H6'···H10B | 2.4118 |
N3···H4Aix | 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···O5v | 3.324 (6) | H7B···N4 | 2.7368 |
C2···C4x | 3.367 (6) | H7B···H2' | 2.3882 |
C2···N4x | 3.414 (6) | H7B···H4B | 2.2138 |
C3'···C10ii | 3.550 (8) | H8A···O2i | 2.6001 |
C4···C2x | 3.367 (6) | H8A···O3i | 2.6065 |
C4···N3x | 3.436 (6) | H8A···C9i | 2.8056 |
C4···C6' | 3.534 (6) | H8B···H2' | 2.2552 |
C6···C6' | 3.556 (7) | H8B···O3ii | 2.8700 |
C6···N4iv | 3.357 (6) | H8B···C2' | 2.7368 |
C6'···C4 | 3.534 (6) | H8C···C14xi | 3.0831 |
C6'···C6 | 3.556 (7) | H8C···H2' | 2.4545 |
C8···O3i | 3.329 (8) | H8C···C2' | 2.8456 |
C9···O1 | 3.290 (7) | H9A···C3' | 3.0414 |
C9···O3 | 3.249 (7) | H9A···H10Cii | 2.5202 |
C10···O1viii | 3.355 (8) | H9A···O1 | 2.8863 |
C10···O1iii | 3.352 (8) | H9C···O3 | 2.8297 |
C10···C3'viii | 3.550 (8) | H9C···C5' | 2.9353 |
C11···O6 | 3.094 (7) | H10A···O2iii | 2.7129 |
C13···O6iv | 3.344 (7) | H10A···O1iii | 2.6674 |
C14···O4 | 3.085 (7) | H10B···C6' | 2.7785 |
C1'···H4B | 2.7991 | H10B···H6' | 2.4118 |
C2···H4Aix | 3.0891 | H10C···H6' | 2.2118 |
C2'···H8B | 2.7368 | H10C···O1viii | 2.5893 |
C2'···H8C | 2.8456 | H10C···C6' | 2.6945 |
C3'···H7Av | 2.9041 | H10C···C8viii | 3.0607 |
C3'···H9A | 3.0414 | H10C···H9Aviii | 2.5202 |
C3'···H10Cii | 3.0074 | H10C···C3'viii | 3.0074 |
C4···H4Aix | 3.0141 | H12···O4iv | 2.7346 |
C4'···H7Av | 2.9303 | H13···O6iv | 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) top
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···O7vi | 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···N3ix | 0.8603 | 2.1306 | 2.985 (5) | 172.14 |
N4—H4B···O7xi | 0.8594 | 2.1365 | 2.829 (6) | 137.28 |
C10—H10C···O1viii | 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. |
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