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In the title compound, trimethoprim tri­fluoro­acetate [or 2,4-di­amino-5-(3,4,5-tri­methoxy­benzyl)­pyrimidin-1-ium tri­fluoro­acetate], C14H19N4O3+·C2F3O2, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802009509/cv6116sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802009509/cv6116Isup2.hkl
Contains datablock I

CCDC reference: 189886

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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


Red Alert 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?)
Amber Alert Alert Level B:
PLAT_031 Alert B Refined Extinction parameter within range .... 1.93 Sigma
Yellow Alert 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

Computing details top

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+·C2F3O2F(000) = 840
Mr = 404.35Dx = 1.471 Mg m3
Monoclinic, P21/aMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yabCell parameters from 25 reflections
a = 10.380 (2) Åθ = 2.1–30.2°
b = 19.091 (3) ŵ = 0.13 mm1
c = 9.947 (2) ÅT = 293 K
β = 112.17 (2)°Needle, colourless
V = 1825.4 (6) Å30.31 × 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 tubeRint = 0.050
Graphite monochromatorθmax = 31.7°, θmin = 2.1°
ω–2θ scansh = 1313
26370 measured reflectionsk = 2727
5238 independent reflectionsl = 1414
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059H 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 reflectionsΔρmax = 0.89 e Å3
330 parametersΔρmin = 0.58 e Å3
0 restraintsExtinction correction: SHELXL97, Fc* = kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraintsExtinction 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
xyzUiso*/Ueq
F10.4475 (2)0.16233 (12)0.3157 (2)0.0936 (9)
F20.4714 (2)0.09689 (14)0.1676 (4)0.1359 (13)
F30.3817 (3)0.19790 (16)0.1150 (3)0.1329 (11)
O40.2165 (2)0.08095 (13)0.2557 (2)0.0773 (9)
O50.1433 (2)0.11576 (12)0.0341 (2)0.0651 (7)
C110.2315 (3)0.10962 (13)0.1552 (3)0.0460 (8)
C120.3828 (3)0.14051 (15)0.1863 (3)0.0502 (9)
O10.11771 (19)0.31918 (8)0.82547 (18)0.0478 (6)
O20.23186 (19)0.39773 (8)0.68314 (18)0.0467 (5)
O30.3141 (2)0.34283 (8)0.48532 (18)0.0499 (6)
N10.0385 (2)0.01329 (10)0.7924 (2)0.0411 (6)
N20.1432 (3)0.07531 (13)0.9951 (3)0.0552 (8)
N30.2908 (2)0.01012 (10)0.9143 (2)0.0397 (6)
N40.4337 (2)0.05719 (12)0.8368 (3)0.0479 (8)
C1'0.2057 (2)0.18174 (11)0.6194 (2)0.0344 (6)
C20.1592 (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)
C40.3013 (2)0.03427 (11)0.8185 (2)0.0366 (7)
C4'0.2196 (2)0.32633 (11)0.6575 (2)0.0365 (7)
C50.1775 (2)0.05658 (11)0.7008 (2)0.0356 (6)
C5'0.2649 (2)0.29652 (11)0.5579 (2)0.0375 (7)
C60.0493 (3)0.03106 (12)0.6941 (3)0.0400 (7)
C6'0.2587 (3)0.22399 (12)0.5400 (2)0.0378 (7)
C70.1888 (3)0.10367 (12)0.5876 (3)0.0395 (8)
C80.0695 (4)0.27814 (17)0.9144 (3)0.0608 (13)
C90.1219 (4)0.43876 (16)0.5805 (4)0.0580 (10)
C100.3340 (4)0.31743 (19)0.3649 (3)0.0628 (13)
H10.045 (3)0.0308 (16)0.783 (3)0.067 (9)*
H2'0.127 (3)0.1823 (13)0.768 (3)0.045 (7)*
H2A0.052 (4)0.0875 (18)0.994 (4)0.086 (11)*
H2B0.219 (3)0.0876 (15)1.067 (3)0.056 (8)*
H4A0.512 (4)0.0447 (17)0.907 (4)0.074 (10)*
H4B0.446 (3)0.0886 (15)0.781 (3)0.052 (8)*
H60.039 (3)0.0435 (12)0.622 (3)0.038 (6)*
H6'0.291 (3)0.2014 (13)0.476 (3)0.047 (7)*
H7A0.278 (3)0.0904 (13)0.570 (3)0.050 (7)*
H7B0.098 (3)0.0954 (14)0.502 (3)0.051 (7)*
H8A0.059 (4)0.3162 (19)0.982 (4)0.097 (11)*
H8B0.030 (4)0.2518 (19)0.867 (4)0.085 (11)*
H8C0.152 (4)0.249 (2)0.969 (4)0.097 (12)*
H9A0.118 (4)0.483 (2)0.617 (4)0.098 (12)*
H9B0.140 (5)0.441 (2)0.497 (5)0.120 (16)*
H9C0.021 (4)0.4232 (18)0.558 (4)0.083 (11)*
H10A0.248 (3)0.2922 (16)0.303 (3)0.059 (8)*
H10B0.349 (3)0.3582 (19)0.312 (4)0.083 (10)*
H10C0.420 (4)0.2892 (17)0.388 (3)0.072 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0902 (15)0.1141 (17)0.0756 (13)0.0402 (12)0.0304 (12)0.0292 (12)
F20.0738 (15)0.126 (2)0.224 (3)0.0138 (13)0.0744 (18)0.096 (2)
F30.0837 (16)0.161 (2)0.142 (2)0.0300 (15)0.0291 (15)0.0857 (19)
O40.0668 (14)0.1024 (18)0.0597 (12)0.0248 (12)0.0203 (10)0.0280 (12)
O50.0596 (12)0.0801 (15)0.0501 (11)0.0080 (10)0.0143 (10)0.0126 (10)
C110.0501 (15)0.0404 (13)0.0507 (15)0.0002 (11)0.0225 (12)0.0060 (11)
C120.0512 (15)0.0575 (16)0.0455 (14)0.0006 (12)0.0224 (12)0.0062 (12)
O10.0716 (12)0.0382 (9)0.0442 (9)0.0045 (8)0.0339 (9)0.0055 (7)
O20.0645 (11)0.0282 (8)0.0411 (9)0.0003 (7)0.0128 (8)0.0026 (7)
O30.0755 (12)0.0383 (9)0.0450 (9)0.0073 (8)0.0330 (9)0.0030 (7)
N10.0397 (11)0.0446 (11)0.0386 (10)0.0045 (9)0.0144 (9)0.0058 (8)
N20.0470 (14)0.0664 (15)0.0488 (13)0.0054 (11)0.0141 (11)0.0242 (11)
N30.0413 (11)0.0376 (10)0.0398 (10)0.0009 (8)0.0149 (8)0.0063 (8)
N40.0463 (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)
C20.0443 (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)
C40.0440 (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)
C50.0493 (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)
C60.0439 (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)
C70.0540 (15)0.0338 (12)0.0355 (12)0.0005 (10)0.0222 (11)0.0006 (9)
C80.094 (3)0.0520 (17)0.0555 (17)0.0138 (17)0.0500 (18)0.0032 (14)
C90.074 (2)0.0368 (14)0.0559 (17)0.0122 (14)0.0162 (15)0.0035 (13)
C100.092 (3)0.0614 (19)0.0478 (16)0.0151 (19)0.0410 (17)0.0003 (14)
Geometric parameters (Å, º) top
F1—C121.276 (3)C1'—C71.520 (3)
F2—C121.305 (4)C1'—C2'1.366 (3)
F3—C121.303 (4)C2'—C3'1.396 (3)
O4—C111.200 (4)C3'—C4'1.378 (3)
O5—C111.213 (3)C4—C51.438 (3)
O1—C3'1.357 (3)C4'—C5'1.370 (3)
O1—C81.407 (4)C5—C71.480 (3)
O2—C4'1.384 (3)C5—C61.395 (4)
O2—C91.442 (4)C5'—C6'1.394 (3)
O3—C101.378 (4)C2'—H2'0.89 (3)
O3—C5'1.357 (3)C6—H60.96 (3)
N1—C21.361 (3)C6'—H6'0.93 (3)
N1—C61.330 (3)C7—H7A1.04 (3)
N2—C21.298 (3)C7—H7B1.02 (3)
N3—C21.390 (3)C8—H8A1.02 (4)
N3—C41.310 (3)C8—H8B1.08 (4)
N4—C41.387 (3)C8—H8C0.99 (4)
N1—H10.90 (3)C9—H9A0.93 (4)
N2—H2A0.97 (4)C9—H9B0.92 (5)
N2—H2B0.87 (3)C9—H9C1.03 (4)
N4—H4B0.86 (3)C10—H10A1.00 (3)
N4—H4A0.88 (4)C10—H10B0.98 (4)
C11—C121.595 (5)C10—H10C0.99 (4)
C1'—C6'1.380 (3)
F1···O42.728 (3)C5···H2'2.60 (3)
F1···C103.291 (4)C5'···H9B3.01 (4)
F1···C9i3.216 (4)C6···H2'3.01 (3)
F1···C5'i3.359 (3)C6'···H10C2.92 (4)
F2···N4ii3.108 (4)C6'···H10A2.66 (3)
F2···O43.100 (3)C7···H4B2.65 (3)
F2···O53.175 (4)C8···H2'2.55 (3)
F3···C8iii3.306 (5)C8···H4Bv2.93 (3)
F3···O52.780 (4)C9···H9Axiii2.93 (4)
F1···H10C2.57 (3)C9···H9Cxiii3.08 (4)
F1···H6'2.77 (3)C10···H6'2.59 (3)
F1···H9Ci2.77 (4)C10···H7Bi3.05 (3)
F2···H4Aii2.83 (3)C11···H2Aviii2.78 (4)
F3···H8Civ2.48 (4)C11···H1viii2.70 (3)
F3···H8Aiii2.65 (4)H1···H2A2.24 (5)
O1···N4v3.065 (3)H1···O4viii1.93 (3)
O1···C93.351 (4)H1···O5viii2.90 (3)
O1···N2vi3.172 (3)H1···C11viii2.70 (3)
O1···O22.631 (3)H2'···O5xi2.88 (3)
O2···O32.639 (3)H2'···C52.60 (3)
O2···O12.631 (3)H2'···C63.01 (3)
O2···N2vi3.010 (3)H2'···C82.55 (3)
O3···C93.107 (4)H2'···H8B2.57 (5)
O3···O22.639 (3)H2'···H8C2.30 (5)
O4···C9vii3.282 (4)H2A···H12.24 (5)
O4···N1viii2.819 (3)H2A···O5viii2.01 (4)
O4···F23.100 (3)H2A···C11viii2.78 (4)
O4···F12.728 (3)H2B···O1ix2.41 (3)
O5···F23.175 (4)H2B···O2ix2.36 (3)
O5···N2viii2.979 (4)H2B···C3'ix3.10 (3)
O5···C2iv3.156 (3)H2B···C4'ix3.05 (3)
O5···F32.780 (4)H4A···F2ii2.83 (3)
O5···C8iv3.305 (4)H4A···N3x2.24 (4)
O1···H2Bvi2.41 (3)H4A···C4x3.08 (4)
O1···H4Bv2.42 (3)H4A···H4Ax2.60 (5)
O2···H2Bvi2.36 (3)H4B···C1'2.99 (3)
O2···H6i2.89 (3)H4B···C72.65 (3)
O3···H6i2.71 (3)H4B···H7A2.16 (4)
O3···H9B2.64 (5)H4B···O1i2.42 (3)
O4···H9Avii2.53 (4)H4B···C8i2.93 (3)
O4···H1viii1.93 (3)H6···H7B2.39 (4)
O5···H2'iv2.88 (3)H6···O2v2.89 (3)
O5···H8Civ2.63 (4)H6···O3v2.71 (3)
O5···H1viii2.90 (3)H6'···F12.77 (3)
O5···H2Aviii2.01 (4)H6'···C102.59 (3)
N1···O4viii2.819 (3)H6'···H7A2.34 (4)
N2···O1ix3.172 (3)H6'···H10A2.36 (4)
N2···O2ix3.010 (3)H6'···H10C2.50 (5)
N2···O5viii2.979 (4)H7A···N42.61 (3)
N3···N4x3.126 (3)H7A···H4B2.16 (4)
N4···F2ii3.108 (4)H7A···H6'2.34 (4)
N4···N3x3.126 (3)H7A···H9Ci2.58 (6)
N4···C8i3.412 (4)H7B···H62.39 (4)
N4···O1i3.065 (3)H7B···C10v3.05 (3)
N3···H4Ax2.24 (4)H8A···F3xii2.65 (4)
N4···H7A2.61 (3)H8A···N4v2.86 (4)
N4···H8Ai2.86 (4)H8B···C2'2.97 (4)
C2···O5xi3.156 (3)H8B···H2'2.57 (5)
C2···C11xi3.590 (3)H8B···C2'v3.09 (4)
C5'···F1v3.359 (3)H8B···C3'v3.02 (4)
C8···F3xii3.306 (5)H8B···C4'v3.04 (4)
C8···N4v3.412 (4)H8C···F3xi2.48 (4)
C8···O5xi3.305 (4)H8C···O5xi2.63 (4)
C9···O13.351 (4)H8C···C2'2.63 (4)
C9···O33.107 (4)H8C···H2'2.30 (5)
C9···C9xiii3.373 (5)H9A···O4xiv2.53 (4)
C9···F1v3.216 (4)H9A···C9xiii2.93 (4)
C9···O4xiv3.282 (4)H9A···H9Cxiii2.53 (5)
C10···F13.291 (4)H9B···O32.64 (5)
C11···C2iv3.590 (3)H9B···C5'3.01 (4)
C1'···H10Cv3.04 (4)H9C···C9xiii3.08 (4)
C1'···H4B2.99 (3)H9C···H9Axiii2.53 (5)
C2···H10Bvii2.95 (4)H9C···F1v2.77 (4)
C2'···H8C2.63 (4)H9C···H7Av2.58 (6)
C2'···H8Bi3.09 (4)H10A···C6'2.66 (3)
C2'···H8B2.97 (4)H10A···H6'2.36 (4)
C3'···H8Bi3.02 (4)H10B···C2xiv2.95 (4)
C3'···H2Bvi3.10 (3)H10C···F12.57 (3)
C4···H4Ax3.08 (4)H10C···C6'2.92 (4)
C4'···H2Bvi3.05 (3)H10C···H6'2.50 (5)
C4'···H8Bi3.04 (4)H10C···C1'i3.04 (4)
C3'—O1—C8116.4 (2)C4—C5—C6118.6 (2)
C4'—O2—C9114.3 (2)C6—C5—C7121.6 (2)
C5'—O3—C10116.3 (2)C4—C5—C7119.8 (2)
C2—N1—C6116.7 (2)O3—C5'—C6'126.0 (2)
C2—N3—C4118.64 (19)C4'—C5'—C6'119.5 (2)
C2—N1—H1122.9 (18)O3—C5'—C4'114.50 (19)
C6—N1—H1120.3 (18)N1—C6—C5122.1 (2)
H2A—N2—H2B121 (3)C1'—C6'—C5'121.1 (2)
C2—N2—H2B116 (2)C1'—C7—C5118.3 (2)
C2—N2—H2A122 (2)C1'—C2'—H2'117.2 (18)
H4A—N4—H4B113 (3)C3'—C2'—H2'123.9 (18)
C4—N4—H4A126 (3)N1—C6—H6112.7 (18)
C4—N4—H4B121 (2)C5—C6—H6125.2 (18)
O5—C11—C12118.4 (3)C1'—C6'—H6'116.4 (16)
O4—C11—O5125.8 (3)C5'—C6'—H6'122.5 (17)
O4—C11—C12115.8 (3)C1'—C7—H7A103.6 (14)
F1—C12—F2102.8 (3)C1'—C7—H7B108.9 (15)
F3—C12—C11113.6 (3)C5—C7—H7A108.2 (15)
F1—C12—F399.7 (3)C5—C7—H7B103.2 (17)
F1—C12—C11114.9 (3)H7A—C7—H7B115 (2)
F2—C12—F3108.7 (3)O1—C8—H8A100 (2)
F2—C12—C11115.6 (2)O1—C8—H8B119 (2)
C6'—C1'—C7119.6 (2)O1—C8—H8C103 (2)
C2'—C1'—C6'119.7 (2)H8A—C8—H8B107 (3)
C2'—C1'—C7120.5 (2)H8A—C8—H8C109 (3)
N1—C2—N3124.68 (19)H8B—C8—H8C117 (3)
N2—C2—N3120.9 (2)O2—C9—H9A111 (2)
N1—C2—N2114.4 (2)O2—C9—H9B107 (3)
C1'—C2'—C3'118.9 (2)O2—C9—H9C118 (2)
O1—C3'—C4'113.96 (19)H9A—C9—H9B111 (3)
C2'—C3'—C4'121.7 (2)H9A—C9—H9C99 (3)
O1—C3'—C2'124.3 (2)H9B—C9—H9C111 (4)
N3—C4—N4117.3 (2)O3—C10—H10A108.3 (18)
N3—C4—C5119.3 (2)O3—C10—H10B107 (2)
N4—C4—C5123.4 (2)O3—C10—H10C114.0 (16)
O2—C4'—C3'120.37 (19)H10A—C10—H10B110 (3)
O2—C4'—C5'120.63 (19)H10A—C10—H10C113 (3)
C3'—C4'—C5'119.0 (2)H10B—C10—H10C104 (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—C525.3 (4)
C9—O2—C4'—C3'98.9 (3)C1'—C2'—C3'—O1178.2 (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'—O24.2 (3)
C6—N1—C2—N31.1 (3)C2'—C3'—C4'—C5'2.4 (3)
C2—N1—C6—C50.3 (3)C2'—C3'—C4'—O2176.1 (2)
C6—N1—C2—N2179.3 (2)N3—C4—C5—C61.2 (3)
C4—N3—C2—N2178.5 (2)N4—C4—C5—C73.1 (3)
C4—N3—C2—N11.9 (3)N3—C4—C5—C7176.7 (2)
C2—N3—C4—N4178.3 (2)N4—C4—C5—C6179.0 (2)
C2—N3—C4—C51.9 (3)C3'—C4'—C5'—O3178.48 (19)
O5—C11—C12—F291.7 (3)O2—C4'—C5'—C6'176.4 (2)
O5—C11—C12—F335.0 (4)O2—C4'—C5'—O33.1 (3)
O4—C11—C12—F132.3 (4)C3'—C4'—C5'—C6'2.1 (3)
O5—C11—C12—F1148.8 (3)C4—C5—C6—N10.3 (3)
O4—C11—C12—F3146.2 (3)C7—C5—C6—N1177.5 (2)
O4—C11—C12—F287.2 (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—C5160.0 (2)
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+1, y, z+1; (iii) x+1/2, y+1/2, z1; (iv) x, y, z1; (v) x1/2, y+1/2, z; (vi) x+1/2, y+1/2, z+2; (vii) x+1/2, y1/2, z+1; (viii) x, y, z+1; (ix) x+1/2, y1/2, z+2; (x) x+1, y, z+2; (xi) x, y, z+1; (xii) x1/2, 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···AD—HH···AD···AD—H···A
N1—H1···O4viii0.90 (3)1.93 (3)2.819 (3)170 (3)
N2—H2A···O5viii0.97 (4)2.01 (4)2.979 (4)173 (3)
N2—H2B···O1ix0.87 (3)2.41 (3)3.172 (3)146 (2)
N2—H2B···O2ix0.87 (3)2.36 (3)3.010 (3)132 (3)
N4—H4A···N3x0.88 (4)2.24 (4)3.126 (3)179 (4)
N4—H4B···O1i0.86 (3)2.42 (3)3.065 (3)132 (2)
C8—H8C···F3xi0.99 (4)2.48 (4)3.457 (5)169 (3)
C9—H9A···O4xiv0.93 (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, y1/2, z+2; (x) x+1, y, z+2; (xi) x, y, z+1; (xiv) x+1/2, y+1/2, z+1.
 

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