In the title compound, trimethoprim trifluoroacetate [or 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidin-1-ium trifluoroacetate], C
14H
19N
4O
3+·C
2F
3O
2−, the trimethoprim molecule is protonated at N-1. The carboxylate group of the trifluoroacetate anion binds with the protonated pyrimidine ring of trimethoprim (TMP) by two nearly parallel N—H
O hydrogen bonds. This is reminiscent of the carboxylate–trimethoprim interaction observed in dihydrofolate reductase (DHFR)–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 atom N3. The 2-amino group of one TMP motif and the 4-amino group of another motif (both of these motifs are members of a base pair) are bridged by one of the methoxy O atom of a third TMP motif, leading to a five-membered (excluding H atoms) hydrogen-bonded chelate. One of the H atoms of the 2-amino group is also involved in a bifurcated hydrogen bond involving two methoxy O atoms of a trimethoprim motif, leading to a five-membered (including the H atom) hydrogen-bonded chelate. The pyrimidine ring makes a dihedral angle of 83.69 (10)° with the phenyl ring in the trimethoprim cation. In the trifluoroacetate moiety, the average F—C bond distance is 1.261 Å and F—C—C and F—C—F bond angles are 114.7 and 103.7° respectively.
Supporting information
CCDC reference: 189886
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.059
- wR factor = 0.188
- Data-to-parameter ratio = 15.9
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level A:
REFLT_03
From the CIF: _diffrn_reflns_theta_max 31.69
From the CIF: _reflns_number_total 5238
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 6176
Completeness (_total/calc) 84.81%
Alert A: < 85% complete (theta max?)
Alert Level B:
PLAT_031 Alert B Refined Extinction parameter within range .... 1.93 Sigma
Alert Level C:
DIFMX_01 Alert C The maximum difference density is > 0.1*ZMAX*0.75
_refine_diff_density_max given = 0.885
Test value = 0.675
DIFMX_02 Alert C The minimum difference density is > 0.1*ZMAX*0.75
The relevant atom site should be identified.
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 31.69
From the CIF: _reflns_number_total 5238
From the CIF: _diffrn_reflns_limit_ max hkl 13. 27. 14.
From the CIF: _diffrn_reflns_limit_ min hkl -13. -27. -14.
TEST1: Expected hkl limits for theta max
Calculated maximum hkl 15. 28. 14.
Calculated minimum hkl -15. -28. -14.
ALERT: Expected hkl max differ from CIF values
1 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
2 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, 1997).
2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidinium trifluoroacetate
top
Crystal data top
C14H19N4O3+·C2F3O2− | F(000) = 840 |
Mr = 404.35 | Dx = 1.471 Mg m−3 |
Monoclinic, P21/a | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2yab | Cell parameters from 25 reflections |
a = 10.380 (2) Å | θ = 2.1–30.2° |
b = 19.091 (3) Å | µ = 0.13 mm−1 |
c = 9.947 (2) Å | T = 293 K |
β = 112.17 (2)° | Needle, colourless |
V = 1825.4 (6) Å3 | 0.31 × 0.27 × 0.16 mm |
Z = 4 | |
Data collection top
Bruker AXS SMART with CCD diffractometer | 2610 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.050 |
Graphite monochromator | θmax = 31.7°, θmin = 2.1° |
ω–2θ scans | h = −13→13 |
26370 measured reflections | k = −27→27 |
5238 independent reflections | l = −14→14 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.059 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.188 | w = 1/[σ2(Fo2) + (0.1018P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max = 0.001 |
5238 reflections | Δρmax = 0.89 e Å−3 |
330 parameters | Δρmin = −0.58 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc* = kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 constraints | Extinction coefficient: 0.0029 (15) |
Primary atom site location: structure-invariant direct methods | |
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 | |
F1 | 0.4475 (2) | 0.16233 (12) | 0.3157 (2) | 0.0936 (9) | |
F2 | 0.4714 (2) | 0.09689 (14) | 0.1676 (4) | 0.1359 (13) | |
F3 | 0.3817 (3) | 0.19790 (16) | 0.1150 (3) | 0.1329 (11) | |
O4 | 0.2165 (2) | 0.08095 (13) | 0.2557 (2) | 0.0773 (9) | |
O5 | 0.1433 (2) | 0.11576 (12) | 0.0341 (2) | 0.0651 (7) | |
C11 | 0.2315 (3) | 0.10962 (13) | 0.1552 (3) | 0.0460 (8) | |
C12 | 0.3828 (3) | 0.14051 (15) | 0.1863 (3) | 0.0502 (9) | |
O1 | 0.11771 (19) | 0.31918 (8) | 0.82547 (18) | 0.0478 (6) | |
O2 | 0.23186 (19) | 0.39773 (8) | 0.68314 (18) | 0.0467 (5) | |
O3 | 0.3141 (2) | 0.34283 (8) | 0.48532 (18) | 0.0499 (6) | |
N1 | 0.0385 (2) | −0.01329 (10) | 0.7924 (2) | 0.0411 (6) | |
N2 | 0.1432 (3) | −0.07531 (13) | 0.9951 (3) | 0.0552 (8) | |
N3 | 0.2908 (2) | −0.01012 (10) | 0.9143 (2) | 0.0397 (6) | |
N4 | 0.4337 (2) | 0.05719 (12) | 0.8368 (3) | 0.0479 (8) | |
C1' | 0.2057 (2) | 0.18174 (11) | 0.6194 (2) | 0.0344 (6) | |
C2 | 0.1592 (2) | −0.03257 (12) | 0.9011 (2) | 0.0387 (7) | |
C2' | 0.1586 (3) | 0.21118 (12) | 0.7175 (2) | 0.0368 (7) | |
C3' | 0.1646 (2) | 0.28386 (11) | 0.7345 (2) | 0.0356 (7) | |
C4 | 0.3013 (2) | 0.03427 (11) | 0.8185 (2) | 0.0366 (7) | |
C4' | 0.2196 (2) | 0.32633 (11) | 0.6575 (2) | 0.0365 (7) | |
C5 | 0.1775 (2) | 0.05658 (11) | 0.7008 (2) | 0.0356 (6) | |
C5' | 0.2649 (2) | 0.29652 (11) | 0.5579 (2) | 0.0375 (7) | |
C6 | 0.0493 (3) | 0.03106 (12) | 0.6941 (3) | 0.0400 (7) | |
C6' | 0.2587 (3) | 0.22399 (12) | 0.5400 (2) | 0.0378 (7) | |
C7 | 0.1888 (3) | 0.10367 (12) | 0.5876 (3) | 0.0395 (8) | |
C8 | 0.0695 (4) | 0.27814 (17) | 0.9144 (3) | 0.0608 (13) | |
C9 | 0.1219 (4) | 0.43876 (16) | 0.5805 (4) | 0.0580 (10) | |
C10 | 0.3340 (4) | 0.31743 (19) | 0.3649 (3) | 0.0628 (13) | |
H1 | −0.045 (3) | −0.0308 (16) | 0.783 (3) | 0.067 (9)* | |
H2' | 0.127 (3) | 0.1823 (13) | 0.768 (3) | 0.045 (7)* | |
H2A | 0.052 (4) | −0.0875 (18) | 0.994 (4) | 0.086 (11)* | |
H2B | 0.219 (3) | −0.0876 (15) | 1.067 (3) | 0.056 (8)* | |
H4A | 0.512 (4) | 0.0447 (17) | 0.907 (4) | 0.074 (10)* | |
H4B | 0.446 (3) | 0.0886 (15) | 0.781 (3) | 0.052 (8)* | |
H6 | −0.039 (3) | 0.0435 (12) | 0.622 (3) | 0.038 (6)* | |
H6' | 0.291 (3) | 0.2014 (13) | 0.476 (3) | 0.047 (7)* | |
H7A | 0.278 (3) | 0.0904 (13) | 0.570 (3) | 0.050 (7)* | |
H7B | 0.098 (3) | 0.0954 (14) | 0.502 (3) | 0.051 (7)* | |
H8A | 0.059 (4) | 0.3162 (19) | 0.982 (4) | 0.097 (11)* | |
H8B | −0.030 (4) | 0.2518 (19) | 0.867 (4) | 0.085 (11)* | |
H8C | 0.152 (4) | 0.249 (2) | 0.969 (4) | 0.097 (12)* | |
H9A | 0.118 (4) | 0.483 (2) | 0.617 (4) | 0.098 (12)* | |
H9B | 0.140 (5) | 0.441 (2) | 0.497 (5) | 0.120 (16)* | |
H9C | 0.021 (4) | 0.4232 (18) | 0.558 (4) | 0.083 (11)* | |
H10A | 0.248 (3) | 0.2922 (16) | 0.303 (3) | 0.059 (8)* | |
H10B | 0.349 (3) | 0.3582 (19) | 0.312 (4) | 0.083 (10)* | |
H10C | 0.420 (4) | 0.2892 (17) | 0.388 (3) | 0.072 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.0902 (15) | 0.1141 (17) | 0.0756 (13) | −0.0402 (12) | 0.0304 (12) | −0.0292 (12) |
F2 | 0.0738 (15) | 0.126 (2) | 0.224 (3) | −0.0138 (13) | 0.0744 (18) | −0.096 (2) |
F3 | 0.0837 (16) | 0.161 (2) | 0.142 (2) | −0.0300 (15) | 0.0291 (15) | 0.0857 (19) |
O4 | 0.0668 (14) | 0.1024 (18) | 0.0597 (12) | −0.0248 (12) | 0.0203 (10) | 0.0280 (12) |
O5 | 0.0596 (12) | 0.0801 (15) | 0.0501 (11) | −0.0080 (10) | 0.0143 (10) | 0.0126 (10) |
C11 | 0.0501 (15) | 0.0404 (13) | 0.0507 (15) | 0.0002 (11) | 0.0225 (12) | 0.0060 (11) |
C12 | 0.0512 (15) | 0.0575 (16) | 0.0455 (14) | 0.0006 (12) | 0.0224 (12) | 0.0062 (12) |
O1 | 0.0716 (12) | 0.0382 (9) | 0.0442 (9) | 0.0045 (8) | 0.0339 (9) | −0.0055 (7) |
O2 | 0.0645 (11) | 0.0282 (8) | 0.0411 (9) | −0.0003 (7) | 0.0128 (8) | −0.0026 (7) |
O3 | 0.0755 (12) | 0.0383 (9) | 0.0450 (9) | −0.0073 (8) | 0.0330 (9) | 0.0030 (7) |
N1 | 0.0397 (11) | 0.0446 (11) | 0.0386 (10) | −0.0045 (9) | 0.0144 (9) | 0.0058 (8) |
N2 | 0.0470 (14) | 0.0664 (15) | 0.0488 (13) | −0.0054 (11) | 0.0141 (11) | 0.0242 (11) |
N3 | 0.0413 (11) | 0.0376 (10) | 0.0398 (10) | −0.0009 (8) | 0.0149 (8) | 0.0063 (8) |
N4 | 0.0463 (13) | 0.0465 (13) | 0.0506 (13) | −0.0060 (10) | 0.0181 (11) | 0.0128 (10) |
C1' | 0.0413 (12) | 0.0311 (11) | 0.0314 (10) | 0.0032 (9) | 0.0143 (9) | 0.0017 (8) |
C2 | 0.0443 (13) | 0.0337 (11) | 0.0381 (12) | −0.0018 (10) | 0.0155 (10) | 0.0032 (9) |
C2' | 0.0458 (13) | 0.0335 (12) | 0.0351 (11) | −0.0006 (10) | 0.0199 (10) | 0.0002 (9) |
C3' | 0.0421 (12) | 0.0350 (12) | 0.0308 (10) | 0.0029 (9) | 0.0151 (9) | −0.0018 (8) |
C4 | 0.0440 (13) | 0.0287 (10) | 0.0395 (11) | −0.0010 (9) | 0.0184 (10) | −0.0012 (9) |
C4' | 0.0456 (13) | 0.0270 (10) | 0.0346 (11) | 0.0012 (9) | 0.0125 (10) | −0.0011 (8) |
C5 | 0.0493 (13) | 0.0268 (10) | 0.0333 (10) | −0.0010 (9) | 0.0184 (10) | −0.0016 (8) |
C5' | 0.0460 (13) | 0.0338 (11) | 0.0343 (11) | 0.0016 (10) | 0.0170 (10) | 0.0053 (9) |
C6 | 0.0439 (13) | 0.0393 (12) | 0.0350 (11) | 0.0026 (10) | 0.0129 (10) | 0.0036 (9) |
C6' | 0.0490 (14) | 0.0341 (12) | 0.0346 (11) | 0.0030 (10) | 0.0207 (10) | 0.0009 (9) |
C7 | 0.0540 (15) | 0.0338 (12) | 0.0355 (12) | −0.0005 (10) | 0.0222 (11) | −0.0006 (9) |
C8 | 0.094 (3) | 0.0520 (17) | 0.0555 (17) | 0.0138 (17) | 0.0500 (18) | 0.0032 (14) |
C9 | 0.074 (2) | 0.0368 (14) | 0.0559 (17) | 0.0122 (14) | 0.0162 (15) | 0.0035 (13) |
C10 | 0.092 (3) | 0.0614 (19) | 0.0478 (16) | −0.0151 (19) | 0.0410 (17) | −0.0003 (14) |
Geometric parameters (Å, º) top
F1—C12 | 1.276 (3) | C1'—C7 | 1.520 (3) |
F2—C12 | 1.305 (4) | C1'—C2' | 1.366 (3) |
F3—C12 | 1.303 (4) | C2'—C3' | 1.396 (3) |
O4—C11 | 1.200 (4) | C3'—C4' | 1.378 (3) |
O5—C11 | 1.213 (3) | C4—C5 | 1.438 (3) |
O1—C3' | 1.357 (3) | C4'—C5' | 1.370 (3) |
O1—C8 | 1.407 (4) | C5—C7 | 1.480 (3) |
O2—C4' | 1.384 (3) | C5—C6 | 1.395 (4) |
O2—C9 | 1.442 (4) | C5'—C6' | 1.394 (3) |
O3—C10 | 1.378 (4) | C2'—H2' | 0.89 (3) |
O3—C5' | 1.357 (3) | C6—H6 | 0.96 (3) |
N1—C2 | 1.361 (3) | C6'—H6' | 0.93 (3) |
N1—C6 | 1.330 (3) | C7—H7A | 1.04 (3) |
N2—C2 | 1.298 (3) | C7—H7B | 1.02 (3) |
N3—C2 | 1.390 (3) | C8—H8A | 1.02 (4) |
N3—C4 | 1.310 (3) | C8—H8B | 1.08 (4) |
N4—C4 | 1.387 (3) | C8—H8C | 0.99 (4) |
N1—H1 | 0.90 (3) | C9—H9A | 0.93 (4) |
N2—H2A | 0.97 (4) | C9—H9B | 0.92 (5) |
N2—H2B | 0.87 (3) | C9—H9C | 1.03 (4) |
N4—H4B | 0.86 (3) | C10—H10A | 1.00 (3) |
N4—H4A | 0.88 (4) | C10—H10B | 0.98 (4) |
C11—C12 | 1.595 (5) | C10—H10C | 0.99 (4) |
C1'—C6' | 1.380 (3) | | |
| | | |
F1···O4 | 2.728 (3) | C5···H2' | 2.60 (3) |
F1···C10 | 3.291 (4) | C5'···H9B | 3.01 (4) |
F1···C9i | 3.216 (4) | C6···H2' | 3.01 (3) |
F1···C5'i | 3.359 (3) | C6'···H10C | 2.92 (4) |
F2···N4ii | 3.108 (4) | C6'···H10A | 2.66 (3) |
F2···O4 | 3.100 (3) | C7···H4B | 2.65 (3) |
F2···O5 | 3.175 (4) | C8···H2' | 2.55 (3) |
F3···C8iii | 3.306 (5) | C8···H4Bv | 2.93 (3) |
F3···O5 | 2.780 (4) | C9···H9Axiii | 2.93 (4) |
F1···H10C | 2.57 (3) | C9···H9Cxiii | 3.08 (4) |
F1···H6' | 2.77 (3) | C10···H6' | 2.59 (3) |
F1···H9Ci | 2.77 (4) | C10···H7Bi | 3.05 (3) |
F2···H4Aii | 2.83 (3) | C11···H2Aviii | 2.78 (4) |
F3···H8Civ | 2.48 (4) | C11···H1viii | 2.70 (3) |
F3···H8Aiii | 2.65 (4) | H1···H2A | 2.24 (5) |
O1···N4v | 3.065 (3) | H1···O4viii | 1.93 (3) |
O1···C9 | 3.351 (4) | H1···O5viii | 2.90 (3) |
O1···N2vi | 3.172 (3) | H1···C11viii | 2.70 (3) |
O1···O2 | 2.631 (3) | H2'···O5xi | 2.88 (3) |
O2···O3 | 2.639 (3) | H2'···C5 | 2.60 (3) |
O2···O1 | 2.631 (3) | H2'···C6 | 3.01 (3) |
O2···N2vi | 3.010 (3) | H2'···C8 | 2.55 (3) |
O3···C9 | 3.107 (4) | H2'···H8B | 2.57 (5) |
O3···O2 | 2.639 (3) | H2'···H8C | 2.30 (5) |
O4···C9vii | 3.282 (4) | H2A···H1 | 2.24 (5) |
O4···N1viii | 2.819 (3) | H2A···O5viii | 2.01 (4) |
O4···F2 | 3.100 (3) | H2A···C11viii | 2.78 (4) |
O4···F1 | 2.728 (3) | H2B···O1ix | 2.41 (3) |
O5···F2 | 3.175 (4) | H2B···O2ix | 2.36 (3) |
O5···N2viii | 2.979 (4) | H2B···C3'ix | 3.10 (3) |
O5···C2iv | 3.156 (3) | H2B···C4'ix | 3.05 (3) |
O5···F3 | 2.780 (4) | H4A···F2ii | 2.83 (3) |
O5···C8iv | 3.305 (4) | H4A···N3x | 2.24 (4) |
O1···H2Bvi | 2.41 (3) | H4A···C4x | 3.08 (4) |
O1···H4Bv | 2.42 (3) | H4A···H4Ax | 2.60 (5) |
O2···H2Bvi | 2.36 (3) | H4B···C1' | 2.99 (3) |
O2···H6i | 2.89 (3) | H4B···C7 | 2.65 (3) |
O3···H6i | 2.71 (3) | H4B···H7A | 2.16 (4) |
O3···H9B | 2.64 (5) | H4B···O1i | 2.42 (3) |
O4···H9Avii | 2.53 (4) | H4B···C8i | 2.93 (3) |
O4···H1viii | 1.93 (3) | H6···H7B | 2.39 (4) |
O5···H2'iv | 2.88 (3) | H6···O2v | 2.89 (3) |
O5···H8Civ | 2.63 (4) | H6···O3v | 2.71 (3) |
O5···H1viii | 2.90 (3) | H6'···F1 | 2.77 (3) |
O5···H2Aviii | 2.01 (4) | H6'···C10 | 2.59 (3) |
N1···O4viii | 2.819 (3) | H6'···H7A | 2.34 (4) |
N2···O1ix | 3.172 (3) | H6'···H10A | 2.36 (4) |
N2···O2ix | 3.010 (3) | H6'···H10C | 2.50 (5) |
N2···O5viii | 2.979 (4) | H7A···N4 | 2.61 (3) |
N3···N4x | 3.126 (3) | H7A···H4B | 2.16 (4) |
N4···F2ii | 3.108 (4) | H7A···H6' | 2.34 (4) |
N4···N3x | 3.126 (3) | H7A···H9Ci | 2.58 (6) |
N4···C8i | 3.412 (4) | H7B···H6 | 2.39 (4) |
N4···O1i | 3.065 (3) | H7B···C10v | 3.05 (3) |
N3···H4Ax | 2.24 (4) | H8A···F3xii | 2.65 (4) |
N4···H7A | 2.61 (3) | H8A···N4v | 2.86 (4) |
N4···H8Ai | 2.86 (4) | H8B···C2' | 2.97 (4) |
C2···O5xi | 3.156 (3) | H8B···H2' | 2.57 (5) |
C2···C11xi | 3.590 (3) | H8B···C2'v | 3.09 (4) |
C5'···F1v | 3.359 (3) | H8B···C3'v | 3.02 (4) |
C8···F3xii | 3.306 (5) | H8B···C4'v | 3.04 (4) |
C8···N4v | 3.412 (4) | H8C···F3xi | 2.48 (4) |
C8···O5xi | 3.305 (4) | H8C···O5xi | 2.63 (4) |
C9···O1 | 3.351 (4) | H8C···C2' | 2.63 (4) |
C9···O3 | 3.107 (4) | H8C···H2' | 2.30 (5) |
C9···C9xiii | 3.373 (5) | H9A···O4xiv | 2.53 (4) |
C9···F1v | 3.216 (4) | H9A···C9xiii | 2.93 (4) |
C9···O4xiv | 3.282 (4) | H9A···H9Cxiii | 2.53 (5) |
C10···F1 | 3.291 (4) | H9B···O3 | 2.64 (5) |
C11···C2iv | 3.590 (3) | H9B···C5' | 3.01 (4) |
C1'···H10Cv | 3.04 (4) | H9C···C9xiii | 3.08 (4) |
C1'···H4B | 2.99 (3) | H9C···H9Axiii | 2.53 (5) |
C2···H10Bvii | 2.95 (4) | H9C···F1v | 2.77 (4) |
C2'···H8C | 2.63 (4) | H9C···H7Av | 2.58 (6) |
C2'···H8Bi | 3.09 (4) | H10A···C6' | 2.66 (3) |
C2'···H8B | 2.97 (4) | H10A···H6' | 2.36 (4) |
C3'···H8Bi | 3.02 (4) | H10B···C2xiv | 2.95 (4) |
C3'···H2Bvi | 3.10 (3) | H10C···F1 | 2.57 (3) |
C4···H4Ax | 3.08 (4) | H10C···C6' | 2.92 (4) |
C4'···H2Bvi | 3.05 (3) | H10C···H6' | 2.50 (5) |
C4'···H8Bi | 3.04 (4) | H10C···C1'i | 3.04 (4) |
| | | |
C3'—O1—C8 | 116.4 (2) | C4—C5—C6 | 118.6 (2) |
C4'—O2—C9 | 114.3 (2) | C6—C5—C7 | 121.6 (2) |
C5'—O3—C10 | 116.3 (2) | C4—C5—C7 | 119.8 (2) |
C2—N1—C6 | 116.7 (2) | O3—C5'—C6' | 126.0 (2) |
C2—N3—C4 | 118.64 (19) | C4'—C5'—C6' | 119.5 (2) |
C2—N1—H1 | 122.9 (18) | O3—C5'—C4' | 114.50 (19) |
C6—N1—H1 | 120.3 (18) | N1—C6—C5 | 122.1 (2) |
H2A—N2—H2B | 121 (3) | C1'—C6'—C5' | 121.1 (2) |
C2—N2—H2B | 116 (2) | C1'—C7—C5 | 118.3 (2) |
C2—N2—H2A | 122 (2) | C1'—C2'—H2' | 117.2 (18) |
H4A—N4—H4B | 113 (3) | C3'—C2'—H2' | 123.9 (18) |
C4—N4—H4A | 126 (3) | N1—C6—H6 | 112.7 (18) |
C4—N4—H4B | 121 (2) | C5—C6—H6 | 125.2 (18) |
O5—C11—C12 | 118.4 (3) | C1'—C6'—H6' | 116.4 (16) |
O4—C11—O5 | 125.8 (3) | C5'—C6'—H6' | 122.5 (17) |
O4—C11—C12 | 115.8 (3) | C1'—C7—H7A | 103.6 (14) |
F1—C12—F2 | 102.8 (3) | C1'—C7—H7B | 108.9 (15) |
F3—C12—C11 | 113.6 (3) | C5—C7—H7A | 108.2 (15) |
F1—C12—F3 | 99.7 (3) | C5—C7—H7B | 103.2 (17) |
F1—C12—C11 | 114.9 (3) | H7A—C7—H7B | 115 (2) |
F2—C12—F3 | 108.7 (3) | O1—C8—H8A | 100 (2) |
F2—C12—C11 | 115.6 (2) | O1—C8—H8B | 119 (2) |
C6'—C1'—C7 | 119.6 (2) | O1—C8—H8C | 103 (2) |
C2'—C1'—C6' | 119.7 (2) | H8A—C8—H8B | 107 (3) |
C2'—C1'—C7 | 120.5 (2) | H8A—C8—H8C | 109 (3) |
N1—C2—N3 | 124.68 (19) | H8B—C8—H8C | 117 (3) |
N2—C2—N3 | 120.9 (2) | O2—C9—H9A | 111 (2) |
N1—C2—N2 | 114.4 (2) | O2—C9—H9B | 107 (3) |
C1'—C2'—C3' | 118.9 (2) | O2—C9—H9C | 118 (2) |
O1—C3'—C4' | 113.96 (19) | H9A—C9—H9B | 111 (3) |
C2'—C3'—C4' | 121.7 (2) | H9A—C9—H9C | 99 (3) |
O1—C3'—C2' | 124.3 (2) | H9B—C9—H9C | 111 (4) |
N3—C4—N4 | 117.3 (2) | O3—C10—H10A | 108.3 (18) |
N3—C4—C5 | 119.3 (2) | O3—C10—H10B | 107 (2) |
N4—C4—C5 | 123.4 (2) | O3—C10—H10C | 114.0 (16) |
O2—C4'—C3' | 120.37 (19) | H10A—C10—H10B | 110 (3) |
O2—C4'—C5' | 120.63 (19) | H10A—C10—H10C | 113 (3) |
C3'—C4'—C5' | 119.0 (2) | H10B—C10—H10C | 104 (3) |
| | | |
C8—O1—C3'—C4' | −175.6 (2) | C7—C1'—C6'—C5' | 174.6 (2) |
C8—O1—C3'—C2' | 4.6 (3) | C2'—C1'—C7—C5 | −25.3 (4) |
C9—O2—C4'—C3' | −98.9 (3) | C1'—C2'—C3'—O1 | 178.2 (2) |
C9—O2—C4'—C5' | 82.7 (3) | C1'—C2'—C3'—C4' | −1.5 (3) |
C10—O3—C5'—C6' | 13.4 (4) | O1—C3'—C4'—C5' | −177.34 (19) |
C10—O3—C5'—C4' | −167.2 (2) | O1—C3'—C4'—O2 | 4.2 (3) |
C6—N1—C2—N3 | −1.1 (3) | C2'—C3'—C4'—C5' | 2.4 (3) |
C2—N1—C6—C5 | 0.3 (3) | C2'—C3'—C4'—O2 | −176.1 (2) |
C6—N1—C2—N2 | 179.3 (2) | N3—C4—C5—C6 | 1.2 (3) |
C4—N3—C2—N2 | −178.5 (2) | N4—C4—C5—C7 | 3.1 (3) |
C4—N3—C2—N1 | 1.9 (3) | N3—C4—C5—C7 | −176.7 (2) |
C2—N3—C4—N4 | 178.3 (2) | N4—C4—C5—C6 | −179.0 (2) |
C2—N3—C4—C5 | −1.9 (3) | C3'—C4'—C5'—O3 | 178.48 (19) |
O5—C11—C12—F2 | −91.7 (3) | O2—C4'—C5'—C6' | 176.4 (2) |
O5—C11—C12—F3 | 35.0 (4) | O2—C4'—C5'—O3 | −3.1 (3) |
O4—C11—C12—F1 | −32.3 (4) | C3'—C4'—C5'—C6' | −2.1 (3) |
O5—C11—C12—F1 | 148.8 (3) | C4—C5—C6—N1 | −0.3 (3) |
O4—C11—C12—F3 | −146.2 (3) | C7—C5—C6—N1 | 177.5 (2) |
O4—C11—C12—F2 | 87.2 (4) | C4—C5—C7—C1' | −81.6 (3) |
C2'—C1'—C6'—C5' | −0.1 (4) | C6—C5—C7—C1' | 100.6 (3) |
C7—C1'—C2'—C3' | −174.3 (2) | O3—C5'—C6'—C1' | −179.6 (2) |
C6'—C1'—C2'—C3' | 0.4 (3) | C4'—C5'—C6'—C1' | 1.0 (3) |
C6'—C1'—C7—C5 | 160.0 (2) | | |
Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) −x+1, −y, −z+1; (iii) x+1/2, −y+1/2, z−1; (iv) x, y, z−1; (v) x−1/2, −y+1/2, z; (vi) −x+1/2, y+1/2, −z+2; (vii) −x+1/2, y−1/2, −z+1; (viii) −x, −y, −z+1; (ix) −x+1/2, y−1/2, −z+2; (x) −x+1, −y, −z+2; (xi) x, y, z+1; (xii) x−1/2, −y+1/2, z+1; (xiii) −x, −y+1, −z+1; (xiv) −x+1/2, y+1/2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4viii | 0.90 (3) | 1.93 (3) | 2.819 (3) | 170 (3) |
N2—H2A···O5viii | 0.97 (4) | 2.01 (4) | 2.979 (4) | 173 (3) |
N2—H2B···O1ix | 0.87 (3) | 2.41 (3) | 3.172 (3) | 146 (2) |
N2—H2B···O2ix | 0.87 (3) | 2.36 (3) | 3.010 (3) | 132 (3) |
N4—H4A···N3x | 0.88 (4) | 2.24 (4) | 3.126 (3) | 179 (4) |
N4—H4B···O1i | 0.86 (3) | 2.42 (3) | 3.065 (3) | 132 (2) |
C8—H8C···F3xi | 0.99 (4) | 2.48 (4) | 3.457 (5) | 169 (3) |
C9—H9A···O4xiv | 0.93 (4) | 2.53 (4) | 3.282 (4) | 138 (4) |
Symmetry codes: (i) x+1/2, −y+1/2, z; (viii) −x, −y, −z+1; (ix) −x+1/2, y−1/2, −z+2; (x) −x+1, −y, −z+2; (xi) x, y, z+1; (xiv) −x+1/2, y+1/2, −z+1. |