In the title compound, trimethoprim salicylate methanol solvate [3,4,5-trimethoxybenzyl)pyrimidin-1-ium salicylate methanol solvate], C
14H
19N
4O
3+·C
7H
5O
3−·CH
4O, the trimethoprim molecule is protonated at N1. The carboxylate group of the salicylate ion interacts with the protonated pyrimidine moiety of trimethoprim through a pair of nearly parallel N—H
O hydrogen bonds. This is reminiscent of the carboxylate–trimethoprim interaction observed in dihydrofolate reductase–trimethoprim complexes. The pyrimidine moieties of the trimethoprim cations are centrosymmetrically paired through a pair of N—H
N hydrogen bonds involving the 4-amino group and the unsubstituted pyrimidine N atom. The pyrimidine plane makes a dihedral angle of 89.5 (4)° with the phenyl ring in the trimethoprim cation.
Supporting information
CCDC reference: 180801
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- H-atom completeness 86%
- R factor = 0.063
- wR factor = 0.216
- Data-to-parameter ratio = 10.7
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level B:
PLAT_353 Alert B Long N-H Bond (0.87A) N(2) - H(2B) = 1.09 Ang.
Alert Level C:
DIFMX_01 Alert C The maximum difference density is > 0.1*ZMAX*0.75
_refine_diff_density_max given = 0.621
Test value = 0.600
DIFMX_02 Alert C The minimum difference density is > 0.1*ZMAX*0.75
The relevant atom site should be identified.
PLAT_321 Alert C Check Hybridisation of C(1A) in solvent/ion ?
PLAT_353 Alert C Long N-H Bond (0.87A) N(1) - H(1) = 1.04 Ang.
General Notes
FORMU_01 There is a discrepancy between the atom counts in the
_chemical_formula_sum and the formula from the _atom_site* data.
Atom count from _chemical_formula_sum:C22 H28 N4 O7
Atom count from the _atom_site data: C22 H24 N4 O7
CELLZ_01
From the CIF: _cell_formula_units_Z 2
From the CIF: _chemical_formula_sum C22 H28 N4 O7
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 44.00 44.00 0.00
H 56.00 48.00 8.00
N 8.00 8.00 0.00
O 14.00 14.00 0.00
Difference between formula and atom_site contents detected.
WARNING: H atoms missing from atom site list. Is this intentional?
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
4 Alert Level C = Please check
Data collection: MolEN (Fair, 1990); cell refinement: MolEN; data reduction: MolEN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 1990).
Crystal data top
C14H19N4O3+·C7H5O3−·CH4O | Z = 2 |
Mr = 460.48 | F(000) = 488 |
Triclinic, P1 | Dx = 1.383 Mg m−3 |
a = 10.0139 (19) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.2600 (19) Å | Cell parameters from 25 reflections |
c = 11.984 (9) Å | θ = 10–15° |
α = 105.93 (3)° | µ = 0.10 mm−1 |
β = 109.17 (5)° | T = 293 K |
γ = 92.50 (2)° | Needle, colourless |
V = 1106.1 (10) Å3 | 0.3 × 0.3 × 0.15 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | 2855 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.036 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
ω–2θ scans | h = −11→11 |
Absorption correction: ψ scan (North et al., 1968) | k = −12→12 |
Tmin = 0.97, Tmax = 0.99 | l = −13→14 |
4377 measured reflections | 2 standard reflections every 60 min |
3889 independent reflections | intensity decay: none |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.216 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.65 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
3889 reflections | (Δ/σ)max < 0.001 |
365 parameters | Δρmax = 0.62 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
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 | 0.4218 (2) | 0.6256 (3) | 0.5894 (2) | 0.0823 (9) | |
O2 | 0.4464 (2) | 0.4437 (3) | 0.7128 (2) | 0.0854 (9) | |
O3 | 0.2303 (3) | 0.2147 (3) | 0.6258 (2) | 0.0917 (11) | |
N1 | −0.3240 (2) | 0.0649 (2) | 0.15946 (19) | 0.0437 (7) | |
N2 | −0.3404 (3) | −0.1479 (3) | 0.0256 (2) | 0.0554 (8) | |
N3 | −0.1505 (2) | 0.0151 (2) | 0.06668 (18) | 0.0419 (6) | |
N4 | 0.0411 (2) | 0.1747 (2) | 0.1141 (2) | 0.0491 (7) | |
C2 | −0.2701 (3) | −0.0213 (3) | 0.0832 (2) | 0.0412 (7) | |
C4 | −0.0788 (2) | 0.1423 (2) | 0.1319 (2) | 0.0378 (7) | |
C5 | −0.1277 (2) | 0.2390 (2) | 0.2156 (2) | 0.0398 (7) | |
C6 | −0.2533 (3) | 0.1938 (3) | 0.2231 (2) | 0.0419 (7) | |
C7 | −0.0483 (3) | 0.3805 (3) | 0.2867 (2) | 0.0438 (8) | |
C8 | 0.0865 (2) | 0.3906 (2) | 0.3947 (2) | 0.0385 (7) | |
C9 | 0.1938 (3) | 0.5017 (3) | 0.4352 (3) | 0.0457 (8) | |
C10 | 0.3136 (3) | 0.5178 (3) | 0.5397 (3) | 0.0538 (9) | |
C11 | 0.3263 (3) | 0.4244 (3) | 0.6069 (3) | 0.0564 (9) | |
C12 | 0.2229 (3) | 0.3113 (3) | 0.5624 (2) | 0.0542 (9) | |
C13 | 0.1023 (3) | 0.2964 (3) | 0.4589 (2) | 0.0469 (8) | |
C14 | 0.4159 (6) | 0.7222 (5) | 0.5235 (5) | 0.101 (2) | |
C15 | 0.4187 (4) | 0.4731 (4) | 0.8263 (3) | 0.0823 (13) | |
C16 | 0.3194 (7) | 0.1231 (5) | 0.6157 (5) | 0.129 (3) | |
O4 | 0.4364 (2) | 1.0021 (2) | 0.2017 (2) | 0.0633 (7) | |
O5 | 0.4079 (2) | 0.7936 (2) | 0.07043 (18) | 0.0588 (7) | |
O6 | 0.2159 (3) | 0.6108 (2) | 0.0426 (2) | 0.0743 (8) | |
C1' | 0.2460 (3) | 0.8390 (3) | 0.1789 (2) | 0.0475 (8) | |
C2' | 0.1747 (3) | 0.7053 (3) | 0.1228 (3) | 0.0523 (9) | |
C3' | 0.0546 (3) | 0.6663 (4) | 0.1490 (3) | 0.0668 (11) | |
C4' | 0.0094 (4) | 0.7599 (4) | 0.2305 (4) | 0.0757 (15) | |
C5' | 0.0815 (5) | 0.8911 (5) | 0.2853 (5) | 0.0857 (17) | |
C6' | 0.1987 (3) | 0.9316 (3) | 0.2603 (3) | 0.0656 (11) | |
C7' | 0.3731 (3) | 0.8833 (3) | 0.1496 (2) | 0.0488 (8) | |
O7 | 0.2737 (3) | 0.3882 (3) | 0.1610 (3) | 0.0950 (11) | |
C1A | 0.3360 (10) | 0.2692 (11) | 0.2206 (9) | 0.207 (5) | |
H1 | −0.423 (6) | 0.052 (5) | 0.168 (5) | 0.15 (2)* | |
H2A | −0.319 (4) | −0.208 (4) | −0.022 (4) | 0.081 (12)* | |
H2B | −0.439 (4) | −0.180 (3) | 0.037 (3) | 0.078 (10)* | |
H4A | 0.06893 | 0.11571 | 0.06313 | 0.0589* | |
H4B | 0.09080 | 0.25451 | 0.15345 | 0.0589* | |
H6 | −0.303 (3) | 0.242 (3) | 0.268 (2) | 0.046 (7)* | |
H7A | −0.031 (3) | 0.416 (3) | 0.231 (3) | 0.044 (7)* | |
H7B | −0.102 (4) | 0.437 (3) | 0.318 (3) | 0.068 (9)* | |
H9 | 0.189 (4) | 0.555 (3) | 0.388 (3) | 0.070 (10)* | |
H13 | 0.035 (3) | 0.220 (3) | 0.437 (2) | 0.046 (7)* | |
H14A | 0.418 (5) | 0.689 (4) | 0.441 (5) | 0.109 (15)* | |
H14B | 0.339 (4) | 0.779 (4) | 0.514 (3) | 0.078 (12)* | |
H14C | 0.488 (6) | 0.806 (5) | 0.559 (5) | 0.129 (16)* | |
H15A | 0.36391 | 0.39416 | 0.82663 | 0.1236* | |
H15B | 0.50759 | 0.49596 | 0.89510 | 0.1236* | |
H15C | 0.36586 | 0.54900 | 0.83323 | 0.1236* | |
H16A | 0.41624 | 0.16863 | 0.65622 | 0.1933* | |
H16B | 0.30362 | 0.05605 | 0.65405 | 0.1933* | |
H16C | 0.30240 | 0.07871 | 0.52958 | 0.1933* | |
H3' | 0.022 (4) | 0.565 (4) | 0.108 (3) | 0.084 (11)* | |
H4' | −0.084 (4) | 0.750 (3) | 0.250 (3) | 0.085 (11)* | |
H5' | 0.058 (5) | 0.940 (5) | 0.330 (5) | 0.106 (16)* | |
H6' | 0.249 (4) | 1.021 (3) | 0.295 (3) | 0.065 (9)* | |
H6A | 0.300 (5) | 0.666 (4) | 0.032 (4) | 0.094 (12)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0527 (12) | 0.0803 (16) | 0.0876 (16) | −0.0240 (11) | 0.0289 (12) | −0.0150 (13) |
O2 | 0.0471 (12) | 0.123 (2) | 0.0583 (13) | 0.0211 (12) | 0.0046 (10) | 0.0004 (13) |
O3 | 0.122 (2) | 0.105 (2) | 0.0787 (16) | 0.0501 (17) | 0.0468 (15) | 0.0568 (15) |
N1 | 0.0361 (11) | 0.0499 (12) | 0.0473 (11) | 0.0020 (9) | 0.0194 (9) | 0.0131 (9) |
N2 | 0.0486 (13) | 0.0488 (14) | 0.0656 (15) | −0.0060 (10) | 0.0297 (12) | 0.0030 (12) |
N3 | 0.0348 (10) | 0.0436 (11) | 0.0450 (11) | −0.0021 (8) | 0.0187 (8) | 0.0057 (9) |
N4 | 0.0394 (11) | 0.0469 (12) | 0.0564 (13) | −0.0081 (9) | 0.0245 (10) | 0.0019 (10) |
C2 | 0.0343 (12) | 0.0471 (14) | 0.0422 (12) | −0.0005 (10) | 0.0151 (10) | 0.0127 (10) |
C4 | 0.0306 (11) | 0.0455 (13) | 0.0385 (12) | 0.0011 (10) | 0.0114 (9) | 0.0162 (10) |
C5 | 0.0350 (12) | 0.0439 (13) | 0.0393 (12) | 0.0022 (10) | 0.0134 (10) | 0.0113 (10) |
C6 | 0.0392 (12) | 0.0474 (14) | 0.0419 (12) | 0.0076 (11) | 0.0198 (11) | 0.0110 (10) |
C7 | 0.0430 (13) | 0.0444 (14) | 0.0448 (14) | 0.0064 (11) | 0.0175 (11) | 0.0125 (11) |
C8 | 0.0387 (12) | 0.0357 (12) | 0.0416 (12) | 0.0023 (9) | 0.0187 (10) | 0.0078 (10) |
C9 | 0.0453 (14) | 0.0398 (13) | 0.0532 (15) | 0.0015 (11) | 0.0255 (12) | 0.0068 (12) |
C10 | 0.0355 (13) | 0.0552 (16) | 0.0585 (16) | −0.0053 (11) | 0.0237 (12) | −0.0084 (13) |
C11 | 0.0386 (14) | 0.0768 (19) | 0.0449 (14) | 0.0164 (13) | 0.0130 (12) | 0.0058 (14) |
C12 | 0.0587 (17) | 0.0589 (17) | 0.0466 (15) | 0.0186 (14) | 0.0197 (13) | 0.0160 (13) |
C13 | 0.0546 (15) | 0.0372 (13) | 0.0454 (14) | 0.0012 (12) | 0.0171 (12) | 0.0089 (10) |
C14 | 0.106 (4) | 0.072 (3) | 0.113 (4) | −0.034 (3) | 0.063 (3) | −0.011 (3) |
C15 | 0.084 (2) | 0.104 (3) | 0.0426 (16) | 0.023 (2) | 0.0104 (16) | 0.0102 (17) |
C16 | 0.204 (6) | 0.102 (3) | 0.132 (4) | 0.076 (4) | 0.087 (4) | 0.074 (3) |
O4 | 0.0501 (11) | 0.0606 (12) | 0.0802 (14) | −0.0110 (9) | 0.0311 (10) | 0.0161 (10) |
O5 | 0.0486 (11) | 0.0674 (12) | 0.0612 (12) | −0.0053 (9) | 0.0272 (9) | 0.0137 (10) |
O6 | 0.0708 (14) | 0.0628 (13) | 0.0874 (16) | −0.0140 (11) | 0.0408 (12) | 0.0080 (11) |
C1' | 0.0363 (12) | 0.0592 (16) | 0.0521 (14) | 0.0018 (11) | 0.0147 (11) | 0.0269 (12) |
C2' | 0.0418 (14) | 0.0630 (17) | 0.0558 (16) | −0.0009 (12) | 0.0194 (12) | 0.0228 (13) |
C3' | 0.0518 (17) | 0.075 (2) | 0.080 (2) | −0.0094 (15) | 0.0242 (15) | 0.0353 (18) |
C4' | 0.0564 (18) | 0.091 (3) | 0.105 (3) | 0.0080 (18) | 0.0490 (19) | 0.045 (2) |
C5' | 0.082 (3) | 0.089 (3) | 0.110 (3) | 0.018 (2) | 0.065 (3) | 0.029 (2) |
C6' | 0.0555 (17) | 0.0611 (19) | 0.090 (2) | 0.0021 (15) | 0.0377 (17) | 0.0250 (17) |
C7' | 0.0325 (12) | 0.0626 (16) | 0.0530 (15) | −0.0064 (11) | 0.0136 (11) | 0.0241 (13) |
O7 | 0.0862 (18) | 0.0902 (18) | 0.106 (2) | −0.0091 (14) | 0.0464 (16) | 0.0141 (15) |
C1A | 0.170 (8) | 0.241 (10) | 0.191 (8) | 0.008 (7) | 0.054 (6) | 0.050 (7) |
Geometric parameters (Å, º) top
O1—C10 | 1.365 (4) | C10—C11 | 1.396 (5) |
O1—C14 | 1.419 (6) | C11—C12 | 1.377 (5) |
O2—C11 | 1.391 (4) | C12—C13 | 1.384 (4) |
O2—C15 | 1.431 (4) | C6—H6 | 0.91 (3) |
O3—C12 | 1.396 (4) | C7—H7B | 0.90 (4) |
O3—C16 | 1.333 (7) | C7—H7A | 0.90 (3) |
O4—C7' | 1.238 (4) | C9—H9 | 0.88 (3) |
O5—C7' | 1.278 (4) | C13—H13 | 0.93 (3) |
O6—C2' | 1.348 (4) | C14—H14A | 0.96 (5) |
O6—H6A | 1.06 (5) | C14—H14C | 0.99 (6) |
O7—C1A | 1.626 (12) | C14—H14B | 0.98 (4) |
N1—C6 | 1.357 (4) | C15—H15C | 0.9605 |
N1—C2 | 1.353 (4) | C15—H15B | 0.9596 |
N2—C2 | 1.330 (4) | C15—H15A | 0.9599 |
N3—C2 | 1.331 (4) | C16—H16B | 0.9598 |
N3—C4 | 1.349 (3) | C16—H16A | 0.9598 |
N4—C4 | 1.330 (3) | C16—H16C | 0.9599 |
N1—H1 | 1.04 (6) | C1'—C6' | 1.383 (4) |
N2—H2B | 1.09 (4) | C1'—C2' | 1.392 (5) |
N2—H2A | 0.81 (4) | C1'—C7' | 1.510 (4) |
N4—H4A | 0.8606 | C2'—C3' | 1.407 (5) |
N4—H4B | 0.8596 | C3'—C4' | 1.376 (6) |
C4—C5 | 1.431 (3) | C4'—C5' | 1.372 (7) |
C5—C7 | 1.497 (4) | C5'—C6' | 1.377 (6) |
C5—C6 | 1.361 (4) | C3'—H3' | 1.01 (4) |
C7—C8 | 1.508 (4) | C4'—H4' | 1.04 (4) |
C8—C9 | 1.392 (4) | C5'—H5' | 0.73 (5) |
C8—C13 | 1.376 (4) | C6'—H6' | 0.94 (3) |
C9—C10 | 1.385 (5) | | |
| | | |
O1···O2 | 2.655 (5) | C6···H15Cii | 3.0704 |
O1···C1Ai | 2.651 (11) | C6'···H16Civ | 2.9596 |
O2···C16 | 3.218 (7) | C7···H4B | 2.5780 |
O2···O1 | 2.655 (5) | C7'···H6A | 2.22 (4) |
O2···O3 | 2.832 (5) | C7'···H16Ai | 2.7756 |
O2···C1Ai | 3.327 (12) | C7'···H1v | 2.53 (6) |
O2···O7i | 2.912 (5) | C7'···H2Bv | 2.66 (4) |
O3···C4'ii | 3.364 (6) | C8···H4B | 2.8603 |
O3···C15 | 3.074 (5) | C9···H14B | 2.89 (4) |
O3···O2 | 2.832 (5) | C9···H14A | 2.86 (5) |
O4···C16i | 3.274 (7) | C10···H6ii | 2.91 (3) |
O4···C2iii | 3.337 (4) | C11···H7Bii | 2.96 (4) |
O4···C1Aiv | 2.936 (12) | C11···H16A | 2.9589 |
O4···N1v | 2.696 (4) | C11···H14Ai | 3.02 (5) |
O5···C6iii | 3.388 (4) | C12···H15A | 2.8679 |
O5···N2v | 2.817 (4) | C12···H7Bii | 3.09 (4) |
O5···O6 | 2.499 (4) | C14···H9 | 2.54 (4) |
O6···O5 | 2.499 (4) | C14···H6ii | 3.01 (3) |
O6···O7 | 2.987 (5) | C15···H15Bxi | 3.0939 |
O7···C15i | 3.275 (6) | H1···H2B | 2.43 (6) |
O7···N4 | 2.926 (4) | H1···C7'viii | 2.53 (6) |
O7···N2vi | 3.102 (5) | H1···O4viii | 1.68 (6) |
O7···O2i | 2.912 (5) | H1···O5viii | 2.81 (6) |
O7···O6 | 2.987 (5) | H2A···O7vi | 2.30 (4) |
O1···H6ii | 2.53 (3) | H2A···C1Avi | 2.23 (4) |
O2···H16A | 2.6938 | H2B···C7'viii | 2.66 (4) |
O2···H14Ai | 2.74 (5) | H2B···O5viii | 1.74 (4) |
O3···H15A | 2.4921 | H2B···H1 | 2.43 (6) |
O3···H4'ii | 2.38 (4) | H3'···H7A | 2.54 (5) |
O4···H6' | 2.47 (4) | H3'···H3'iii | 2.45 (5) |
O4···H16Ai | 2.8910 | H3'···O6iii | 2.68 (4) |
O4···H1v | 1.68 (6) | H4'···O3ii | 2.38 (4) |
O4···H16Bi | 2.8050 | H4A···C4vi | 3.0427 |
O4···H14Cvii | 2.83 (5) | H4A···N3vi | 2.1616 |
O5···H6A | 1.52 (5) | H4A···H4Avi | 2.4906 |
O5···H2Bv | 1.74 (4) | H4A···C1A | 2.8072 |
O5···H1v | 2.81 (6) | H4B···O7 | 2.2018 |
O6···H3'iii | 2.68 (4) | H4B···C1A | 2.3028 |
O7···H2Avi | 2.30 (4) | H4B···C8 | 2.8603 |
O7···H15Bi | 2.8000 | H4B···C7 | 2.5780 |
O7···H4B | 2.2018 | H4B···H7A | 2.2742 |
N1···O4viii | 2.696 (4) | H6···C10ii | 2.91 (3) |
N1···C7'viii | 3.440 (5) | H6···C14ii | 3.01 (3) |
N2···O7vi | 3.102 (5) | H6···O1ii | 2.53 (3) |
N2···O5viii | 2.817 (4) | H6···H7B | 2.57 (5) |
N2···C1Avi | 2.886 (10) | H6'···H16Civ | 2.5712 |
N3···N4vi | 3.019 (4) | H6'···C1Aiv | 3.10 (4) |
N3···C7'iii | 3.266 (4) | H6'···O4 | 2.47 (4) |
N4···O7 | 2.926 (4) | H6A···C7' | 2.22 (4) |
N4···N3vi | 3.019 (4) | H6A···O5 | 1.52 (5) |
N4···C8 | 3.353 (4) | H7A···N4 | 2.74 (3) |
N4···C1A | 2.808 (11) | H7A···H3' | 2.54 (5) |
N1···H16Bix | 2.7967 | H7A···H4B | 2.2742 |
N3···H4Avi | 2.1616 | H7A···H9 | 2.44 (5) |
N4···H7A | 2.74 (3) | H7B···C11ii | 2.96 (4) |
C1A···O4x | 2.936 (12) | H7B···C12ii | 3.09 (4) |
C1A···N4 | 2.808 (11) | H7B···H6 | 2.57 (5) |
C1A···O1i | 2.651 (11) | H9···H7A | 2.44 (5) |
C1A···O2i | 3.327 (12) | H9···H14A | 2.42 (7) |
C1A···C14i | 3.227 (12) | H9···C14 | 2.54 (4) |
C1A···N2vi | 2.886 (10) | H9···H14B | 2.47 (5) |
C2···C7'iii | 3.355 (5) | H13···C5 | 2.68 (2) |
C2···O4iii | 3.337 (4) | H14A···H9 | 2.42 (7) |
C4···C13 | 3.581 (4) | H14A···O2i | 2.74 (5) |
C4'···O3ii | 3.364 (6) | H14A···C9 | 2.86 (5) |
C6···O5iii | 3.388 (4) | H14A···C11i | 3.02 (5) |
C7'···N1v | 3.440 (5) | H14B···H9 | 2.47 (5) |
C7'···N3iii | 3.266 (4) | H14B···C9 | 2.89 (4) |
C7'···C16i | 3.439 (7) | H14C···C1Ai | 2.98 (6) |
C7'···C2iii | 3.355 (5) | H14C···O4vii | 2.83 (5) |
C8···N4 | 3.353 (4) | H15A···O3 | 2.4921 |
C13···C4 | 3.581 (4) | H15A···C12 | 2.8679 |
C14···C1Ai | 3.227 (12) | H15B···C15xi | 3.0939 |
C15···O7i | 3.275 (6) | H15B···H15Bxi | 2.5474 |
C15···O3 | 3.074 (5) | H15B···O7i | 2.8000 |
C16···O4i | 3.274 (7) | H15C···C6ii | 3.0704 |
C16···C7'i | 3.439 (7) | H16A···O4i | 2.8910 |
C16···O2 | 3.218 (7) | H16A···C11 | 2.9589 |
C1A···H4B | 2.3028 | H16A···C7'i | 2.7756 |
C1A···H14Ci | 2.98 (6) | H16A···O2 | 2.6938 |
C1A···H2Avi | 2.23 (4) | H16B···N1ix | 2.7967 |
C1A···H6'x | 3.10 (4) | H16B···O4i | 2.8050 |
C1A···H4A | 2.8072 | H16C···C6'x | 2.9596 |
C4···H4Avi | 3.0427 | H16C···H6'x | 2.5712 |
C5···H13 | 2.68 (2) | H16C···C5'x | 3.0742 |
C5'···H16Civ | 3.0742 | | |
| | | |
C10—O1—C14 | 117.3 (3) | C8—C7—H7A | 112 (2) |
C11—O2—C15 | 114.9 (3) | C8—C9—H9 | 119 (2) |
C12—O3—C16 | 118.6 (4) | C10—C9—H9 | 121 (2) |
C2'—O6—H6A | 104 (2) | C8—C13—H13 | 123.5 (16) |
C2—N1—C6 | 119.1 (2) | C12—C13—H13 | 115.7 (17) |
C2—N3—C4 | 118.0 (2) | O1—C14—H14B | 120 (2) |
C2—N1—H1 | 128 (3) | O1—C14—H14C | 120 (3) |
C6—N1—H1 | 112 (3) | H14A—C14—H14B | 103 (4) |
H2A—N2—H2B | 112 (4) | H14A—C14—H14C | 101 (4) |
C2—N2—H2A | 126 (3) | H14B—C14—H14C | 90 (4) |
C2—N2—H2B | 121.5 (18) | O1—C14—H14A | 117 (3) |
C4—N4—H4A | 119.97 | O2—C15—H15B | 109.49 |
H4A—N4—H4B | 119.96 | O2—C15—H15C | 109.43 |
C4—N4—H4B | 120.06 | O2—C15—H15A | 109.48 |
N2—C2—N3 | 120.1 (3) | H15A—C15—H15C | 109.44 |
N1—C2—N2 | 117.1 (3) | H15B—C15—H15C | 109.47 |
N1—C2—N3 | 122.8 (3) | H15A—C15—H15B | 109.51 |
N3—C4—C5 | 122.6 (2) | O3—C16—H16A | 109.46 |
N4—C4—C5 | 121.0 (2) | O3—C16—H16C | 109.46 |
N3—C4—N4 | 116.4 (2) | H16A—C16—H16B | 109.50 |
C6—C5—C7 | 122.7 (2) | O3—C16—H16B | 109.41 |
C4—C5—C7 | 122.3 (2) | H16B—C16—H16C | 109.51 |
C4—C5—C6 | 115.0 (2) | H16A—C16—H16C | 109.50 |
N1—C6—C5 | 122.4 (3) | C2'—C1'—C7' | 120.2 (3) |
C5—C7—C8 | 115.8 (2) | C6'—C1'—C7' | 120.2 (3) |
C7—C8—C9 | 119.5 (2) | C2'—C1'—C6' | 119.7 (3) |
C9—C8—C13 | 119.0 (2) | O6—C2'—C3' | 118.2 (3) |
C7—C8—C13 | 121.3 (2) | C1'—C2'—C3' | 119.5 (3) |
C8—C9—C10 | 120.3 (3) | O6—C2'—C1' | 122.2 (3) |
O1—C10—C11 | 114.9 (3) | C2'—C3'—C4' | 119.9 (4) |
C9—C10—C11 | 120.3 (3) | C3'—C4'—C5' | 119.7 (4) |
O1—C10—C9 | 124.7 (3) | C4'—C5'—C6' | 121.3 (5) |
O2—C11—C12 | 121.7 (3) | C1'—C6'—C5' | 119.9 (4) |
O2—C11—C10 | 119.4 (3) | O4—C7'—C1' | 119.2 (3) |
C10—C11—C12 | 118.8 (3) | O5—C7'—C1' | 116.7 (3) |
O3—C12—C11 | 121.2 (3) | O4—C7'—O5 | 124.0 (3) |
C11—C12—C13 | 120.6 (3) | C2'—C3'—H3' | 109 (2) |
O3—C12—C13 | 118.0 (3) | C4'—C3'—H3' | 130 (2) |
C8—C13—C12 | 120.8 (3) | C3'—C4'—H4' | 128.4 (18) |
N1—C6—H6 | 110.1 (19) | C5'—C4'—H4' | 111.4 (18) |
C5—C6—H6 | 127.5 (19) | C4'—C5'—H5' | 119 (4) |
C5—C7—H7A | 106 (2) | C6'—C5'—H5' | 120 (4) |
C5—C7—H7B | 113 (2) | C1'—C6'—H6' | 117 (2) |
C8—C7—H7B | 106 (2) | C5'—C6'—H6' | 123 (2) |
H7A—C7—H7B | 104 (3) | | |
| | | |
C14—O1—C10—C9 | −5.1 (5) | C8—C9—C10—O1 | −177.4 (3) |
C14—O1—C10—C11 | 178.7 (4) | C8—C9—C10—C11 | −1.4 (5) |
C15—O2—C11—C12 | −69.2 (4) | C9—C10—C11—C12 | 4.6 (5) |
C15—O2—C11—C10 | 114.4 (4) | O1—C10—C11—O2 | −2.5 (4) |
C16—O3—C12—C13 | 107.2 (4) | C9—C10—C11—O2 | −178.9 (3) |
C16—O3—C12—C11 | −78.2 (4) | O1—C10—C11—C12 | −179.0 (3) |
C6—N1—C2—N3 | −0.6 (4) | C10—C11—C12—C13 | −5.5 (5) |
C2—N1—C6—C5 | −1.7 (4) | C10—C11—C12—O3 | 180.0 (3) |
C6—N1—C2—N2 | 178.0 (2) | O2—C11—C12—C13 | 178.1 (3) |
C2—N3—C4—C5 | −1.1 (3) | O2—C11—C12—O3 | 3.6 (5) |
C2—N3—C4—N4 | 179.3 (2) | C11—C12—C13—C8 | 3.3 (4) |
C4—N3—C2—N1 | 1.9 (4) | O3—C12—C13—C8 | 177.9 (3) |
C4—N3—C2—N2 | −176.6 (2) | C6'—C1'—C2'—C3' | 0.5 (5) |
N4—C4—C5—C6 | 178.6 (2) | C6'—C1'—C2'—O6 | 179.9 (3) |
N4—C4—C5—C7 | 0.2 (3) | C2'—C1'—C6'—C5' | 0.0 (5) |
N3—C4—C5—C6 | −1.0 (3) | C7'—C1'—C6'—C5' | 179.1 (3) |
N3—C4—C5—C7 | −179.4 (2) | C2'—C1'—C7'—O4 | −179.0 (3) |
C6—C5—C7—C8 | 107.1 (3) | C2'—C1'—C7'—O5 | 1.4 (4) |
C4—C5—C6—N1 | 2.4 (4) | C6'—C1'—C7'—O4 | 1.9 (4) |
C4—C5—C7—C8 | −74.6 (3) | C6'—C1'—C7'—O5 | −177.7 (3) |
C7—C5—C6—N1 | −179.3 (2) | C7'—C1'—C2'—O6 | 0.8 (4) |
C5—C7—C8—C9 | 155.2 (2) | C7'—C1'—C2'—C3' | −178.7 (3) |
C5—C7—C8—C13 | −28.7 (3) | C1'—C2'—C3'—C4' | −0.6 (5) |
C7—C8—C13—C12 | −176.1 (3) | O6—C2'—C3'—C4' | 179.9 (3) |
C9—C8—C13—C12 | 0.0 (4) | C2'—C3'—C4'—C5' | 0.3 (6) |
C13—C8—C9—C10 | −0.9 (4) | C3'—C4'—C5'—C6' | 0.1 (7) |
C7—C8—C9—C10 | 175.3 (3) | C4'—C5'—C6'—C1' | −0.3 (7) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) −x, −y+1, −z; (iv) x, y+1, z; (v) x+1, y+1, z; (vi) −x, −y, −z; (vii) −x+1, −y+2, −z+1; (viii) x−1, y−1, z; (ix) −x, −y, −z+1; (x) x, y−1, z; (xi) −x+1, −y+1, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4viii | 1.04 (6) | 1.68 (6) | 2.696 (4) | 165 (5) |
N2—H2A···O7vi | 0.81 (4) | 2.30 (4) | 3.102 (5) | 176 (5) |
N2—H2B···O5viii | 1.09 (4) | 1.74 (4) | 2.817 (4) | 171 (2) |
N4—H4A···N3vi | 0.8606 | 2.1616 | 3.019 (4) | 174 |
N4—H4B···O7 | 0.8596 | 2.2018 | 2.926 (4) | 142 |
O6—H6A···O5 | 1.06 (5) | 1.52 (5) | 2.499 (4) | 151 (4) |
C4′—H4′···O3ii | 1.04 (4) | 2.38 (4) | 3.364 (6) | 156 (3) |
C6—H6···O1ii | 0.91 (3) | 2.53 (3) | 3.436 (4) | 175 (2) |
C6′—H6′···O4 | 0.94 (3) | 2.47 (4) | 2.812 (4) | 102 (3) |
C15—H15A···O3 | 0.9599 | 2.4921 | 3.074 (5) | 119 |
Symmetry codes: (ii) −x, −y+1, −z+1; (vi) −x, −y, −z; (viii) x−1, y−1, z. |