In the crystal structure of the title compound, C6H11N3O22+·C4F4O42-, the anions and cations are linked to each other through hydrogen bonds.
Supporting information
CCDC reference: 238696
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.022
- wR factor = 0.056
- Data-to-parameter ratio = 6.3
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact F3 .. C3 .. 2.86 Ang.
Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.34
PLAT431_ALERT_2_C Short Inter HL..A Contact F3 .. O6 .. 2.98 Ang.
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 25.99
From the CIF: _reflns_number_total 1413
Count of symmetry unique reflns 1412
Completeness (_total/calc) 100.07%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1
Fraction of Friedel pairs measured 0.001
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Farrugia, 1997); software used to prepare material for publication: PARST (Nardelli, 1995) and WinGX (Farrugia, 1999).
L-histidinium tetrafluorosuccinate
top
Crystal data top
C6H11N3O22+·C4F4O42− | F(000) = 704 |
Mr = 345.22 | Dx = 1.779 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 21085 reflections |
a = 21.8863 (16) Å | θ = 1.8–29.9° |
b = 5.1411 (4) Å | µ = 0.18 mm−1 |
c = 15.5619 (12) Å | T = 293 K |
β = 132.601 (5)° | Block, colourless |
V = 1288.9 (2) Å3 | 0.56 × 0.48 × 0.36 mm |
Z = 4 | |
Data collection top
Stoe IPDS 2 diffractometer | 1413 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1374 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.032 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 1.8° |
ω scans | h = −26→26 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −6→6 |
Tmin = 0.906, Tmax = 0.938 | l = −19→18 |
12924 measured reflections | |
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)] = 0.022 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.056 | w = 1/[σ2(Fo2) + (0.0296P)2 + 0.5241P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
1413 reflections | Δρmax = 0.22 e Å−3 |
223 parameters | Δρmin = −0.19 e Å−3 |
1 restraint | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0264 (18) |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su'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 |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR
and all goodnesses of fit S are based on F2,
conventional R-factors R are based on F, with F
set to zero for negative F2. The observed criterion of F2 >
σ(F2) is used only for calculating -R-factor-obs
etc. and is not relevant to the choice of reflections for
refinement. R-factors based on F2 are statistically about
twice as large as those based on F, and R-factors based on ALL
data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.24064 (9) | 0.4506 (3) | 0.07144 (13) | 0.0338 (4) | |
O2 | 0.36130 (8) | 0.6629 (3) | 0.17469 (13) | 0.0353 (4) | |
N1 | 0.38737 (10) | 0.5093 (4) | 0.48735 (13) | 0.0319 (5) | |
N2 | 0.30145 (9) | 0.8253 (4) | 0.40107 (13) | 0.0266 (4) | |
N3 | 0.16775 (9) | 0.8316 (4) | 0.09251 (13) | 0.0258 (4) | |
C1 | 0.33574 (10) | 0.8073 (4) | 0.35236 (14) | 0.0229 (5) | |
C2 | 0.38977 (11) | 0.6072 (5) | 0.40733 (15) | 0.0295 (5) | |
C3 | 0.33386 (11) | 0.6453 (5) | 0.48182 (15) | 0.0305 (5) | |
C4 | 0.31258 (11) | 0.9919 (4) | 0.26055 (15) | 0.0236 (5) | |
C5 | 0.25209 (10) | 0.8835 (4) | 0.13627 (14) | 0.0212 (5) | |
C6 | 0.28341 (11) | 0.6383 (4) | 0.12341 (14) | 0.0229 (5) | |
F1 | 0.64530 (7) | 0.1552 (3) | 0.36415 (10) | 0.0360 (3) | |
F2 | 0.58220 (8) | 0.2542 (3) | 0.18492 (12) | 0.0450 (5) | |
F3 | 0.53414 (7) | −0.2686 (2) | 0.27280 (11) | 0.0363 (4) | |
F4 | 0.46968 (7) | −0.1148 (3) | 0.10037 (10) | 0.0418 (4) | |
O3 | 0.69644 (8) | −0.2930 (3) | 0.34758 (12) | 0.0332 (4) | |
O4 | 0.65080 (10) | −0.1545 (4) | 0.17649 (13) | 0.0410 (5) | |
O5 | 0.49928 (8) | 0.1655 (3) | 0.32986 (11) | 0.0335 (4) | |
O6 | 0.41846 (7) | 0.2822 (3) | 0.14309 (11) | 0.0306 (4) | |
C7 | 0.65465 (11) | −0.1541 (4) | 0.25954 (16) | 0.0260 (5) | |
C8 | 0.60086 (12) | 0.0536 (4) | 0.25571 (16) | 0.0264 (5) | |
C9 | 0.51829 (11) | −0.0478 (4) | 0.21401 (15) | 0.0247 (5) | |
C10 | 0.47427 (10) | 0.1533 (4) | 0.23147 (15) | 0.0238 (5) | |
H1N | 0.41940 | 0.39430 | 0.53800 | 0.042 (7)* | |
H2 | 0.42270 | 0.53630 | 0.39850 | 0.053 (8)* | |
H2N | 0.26480 | 0.95700 | 0.38240 | 0.044 (7)* | |
H3 | 0.32350 | 0.64110 | 0.52900 | 0.040 (6)* | |
H3A | 0.16830 | 0.69290 | 0.12920 | 0.040 (7)* | |
H3B | 0.15020 | 0.96760 | 0.10710 | 0.039 (7)* | |
H3C | 0.13000 | 0.80120 | 0.01350 | 0.037 (6)* | |
H4A | 0.29200 | 1.15230 | 0.26590 | 0.030 (6)* | |
H4B | 0.36120 | 1.04420 | 0.27680 | 0.024 (5)* | |
H5 | 0.24610 | 1.00840 | 0.09150 | 0.027 (6)* | |
H22 | 0.3808 (19) | 0.515 (8) | 0.167 (3) | 0.070 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0397 (7) | 0.0217 (7) | 0.0427 (8) | −0.0002 (6) | 0.0290 (7) | −0.0044 (7) |
O2 | 0.0302 (7) | 0.0336 (8) | 0.0455 (8) | 0.0028 (7) | 0.0270 (6) | −0.0092 (7) |
N1 | 0.0302 (8) | 0.0370 (10) | 0.0224 (7) | 0.0094 (8) | 0.0154 (6) | 0.0083 (8) |
N2 | 0.0260 (7) | 0.0320 (9) | 0.0254 (7) | 0.0038 (7) | 0.0189 (6) | −0.0004 (7) |
N3 | 0.0239 (7) | 0.0292 (8) | 0.0245 (7) | 0.0054 (7) | 0.0165 (6) | 0.0032 (7) |
C1 | 0.0202 (7) | 0.0282 (10) | 0.0201 (8) | −0.0001 (8) | 0.0136 (7) | −0.0031 (8) |
C2 | 0.0261 (9) | 0.0381 (11) | 0.0250 (8) | 0.0080 (9) | 0.0176 (7) | 0.0032 (9) |
C3 | 0.0277 (9) | 0.0410 (11) | 0.0227 (8) | 0.0011 (10) | 0.0170 (7) | 0.0015 (9) |
C4 | 0.0274 (8) | 0.0200 (9) | 0.0278 (8) | 0.0004 (8) | 0.0204 (7) | −0.0027 (8) |
C5 | 0.0260 (8) | 0.0201 (9) | 0.0223 (8) | 0.0027 (7) | 0.0183 (7) | 0.0034 (7) |
C6 | 0.0289 (8) | 0.0219 (9) | 0.0220 (8) | 0.0040 (8) | 0.0189 (7) | 0.0030 (7) |
F1 | 0.0287 (5) | 0.0398 (7) | 0.0408 (6) | −0.0082 (6) | 0.0240 (5) | −0.0160 (6) |
F2 | 0.0580 (8) | 0.0317 (7) | 0.0672 (9) | 0.0153 (7) | 0.0511 (7) | 0.0202 (7) |
F3 | 0.0308 (6) | 0.0250 (6) | 0.0497 (7) | 0.0006 (5) | 0.0259 (5) | 0.0063 (6) |
F4 | 0.0343 (6) | 0.0516 (9) | 0.0268 (6) | 0.0053 (6) | 0.0156 (5) | −0.0129 (6) |
O3 | 0.0351 (7) | 0.0342 (8) | 0.0360 (7) | 0.0132 (6) | 0.0264 (6) | 0.0099 (7) |
O4 | 0.0517 (8) | 0.0473 (10) | 0.0434 (8) | 0.0181 (8) | 0.0399 (7) | 0.0113 (8) |
O5 | 0.0310 (6) | 0.0467 (9) | 0.0249 (6) | −0.0063 (7) | 0.0198 (6) | −0.0098 (7) |
O6 | 0.0264 (6) | 0.0339 (8) | 0.0271 (6) | 0.0089 (6) | 0.0164 (6) | −0.0004 (6) |
C7 | 0.0255 (8) | 0.0251 (9) | 0.0335 (9) | 0.0018 (8) | 0.0224 (8) | 0.0009 (8) |
C8 | 0.0299 (9) | 0.0238 (9) | 0.0320 (9) | 0.0029 (8) | 0.0235 (8) | 0.0022 (8) |
C9 | 0.0234 (8) | 0.0251 (9) | 0.0207 (8) | 0.0022 (8) | 0.0130 (7) | −0.0009 (7) |
C10 | 0.0183 (7) | 0.0277 (10) | 0.0244 (8) | −0.0013 (8) | 0.0140 (7) | −0.0047 (8) |
Geometric parameters (Å, º) top
F1—C8 | 1.358 (2) | N2—H2N | 0.9332 |
F2—C8 | 1.355 (3) | N3—H3B | 0.8978 |
F3—C9 | 1.348 (2) | N3—H3C | 0.9185 |
F4—C9 | 1.353 (2) | N3—H3A | 0.9085 |
O1—C6 | 1.199 (3) | C1—C4 | 1.490 (3) |
O2—C6 | 1.310 (3) | C1—C2 | 1.349 (3) |
O2—H22 | 0.92 (5) | C4—C5 | 1.529 (2) |
O3—C7 | 1.236 (2) | C5—C6 | 1.512 (3) |
O4—C7 | 1.237 (3) | C2—H2 | 0.8974 |
O5—C10 | 1.230 (2) | C3—H3 | 0.9035 |
O6—C10 | 1.244 (2) | C4—H4B | 0.9509 |
N1—C3 | 1.316 (4) | C4—H4A | 0.9698 |
N1—C2 | 1.377 (3) | C5—H5 | 0.8895 |
N2—C3 | 1.316 (3) | C7—C8 | 1.560 (4) |
N2—C1 | 1.384 (3) | C8—C9 | 1.540 (4) |
N3—C5 | 1.497 (3) | C9—C10 | 1.557 (4) |
N1—H1N | 0.8451 | | |
| | | |
F1···C3i | 3.368 (3) | N2···N1 | 2.135 (3) |
F1···C3ii | 3.290 (3) | N2···C7x | 3.416 (3) |
F1···O3iii | 3.124 (2) | N2···F1x | 3.181 (3) |
F1···F3 | 2.829 (2) | N2···O3xi | 2.690 (3) |
F1···O3 | 2.649 (2) | N3···O6vii | 2.775 (2) |
F1···C3iv | 3.187 (3) | N3···O4xi | 3.079 (3) |
F1···O5 | 2.862 (3) | N3···O1 | 2.683 (3) |
F1···N2iv | 3.181 (3) | N3···F2x | 3.062 (3) |
F2···N3iv | 3.062 (3) | N3···O4x | 2.958 (3) |
F2···F4 | 2.647 (2) | C1···O2 | 3.256 (3) |
F2···O6 | 3.183 (3) | C2···C2ii | 3.572 (4) |
F2···C7iii | 3.259 (3) | C2···C6 | 3.323 (2) |
F2···O3iii | 3.084 (2) | C2···O2 | 3.244 (3) |
F2···O4 | 2.637 (3) | C2···C4v | 3.585 (3) |
F3···O6v | 2.983 (2) | C3···F1ii | 3.290 (3) |
F3···O3 | 2.897 (3) | C3···F1x | 3.187 (3) |
F3···O5 | 2.696 (2) | C3···C7x | 3.369 (3) |
F3···F1 | 2.829 (2) | C3···F3ix | 2.862 (2) |
F3···C10v | 3.134 (2) | C3···O3ix | 3.158 (3) |
F3···C3i | 2.862 (2) | C3···F1ix | 3.368 (3) |
F3···O2v | 2.991 (3) | C3···O3x | 3.159 (3) |
F3···N1i | 3.083 (2) | C4···C2iii | 3.585 (3) |
F4···F2 | 2.647 (2) | C4···O1iii | 3.229 (2) |
F4···O6 | 2.622 (2) | C4···O4xi | 3.359 (4) |
F1···H3ii | 2.8168 | C5···O1vii | 3.360 (3) |
F2···H3Biv | 2.7065 | C5···O6vii | 3.337 (2) |
F2···H3Aiv | 2.5718 | C5···O1iii | 3.040 (3) |
F3···H22v | 2.78 (5) | C6···C2 | 3.323 (2) |
F3···H3i | 2.5351 | C6···O6 | 3.310 (3) |
F4···H3Cvi | 2.6907 | C6···O1vii | 3.145 (3) |
O1···C5v | 3.040 (3) | C7···C3iv | 3.369 (3) |
O1···C4v | 3.229 (2) | C7···F2v | 3.259 (3) |
O1···N3 | 2.683 (3) | C7···N2iv | 3.416 (3) |
O1···C5vi | 3.360 (3) | C9···O2v | 3.398 (3) |
O1···C6vi | 3.145 (3) | C10···O2v | 3.208 (3) |
O1···O2vi | 3.204 (2) | C10···O2 | 3.286 (3) |
O1···O6vii | 3.231 (2) | C10···F3iii | 3.134 (2) |
O2···O1vii | 3.204 (2) | C1···H3A | 2.9338 |
O2···C10iii | 3.208 (3) | C2···H4Av | 2.9183 |
O2···F3iii | 2.991 (3) | C2···H2ii | 3.0528 |
O2···C10 | 3.286 (3) | C6···H5vi | 3.0206 |
O2···O6 | 2.544 (3) | C7···H3Aiv | 2.8647 |
O2···C1 | 3.256 (3) | C7···H3Bviii | 3.0178 |
O2···C2 | 3.244 (3) | C7···H2Nviii | 2.6879 |
O2···C9iii | 3.398 (3) | C10···H22 | 2.42 (4) |
O3···F3 | 2.897 (3) | C10···H1Nii | 2.9187 |
O3···F2v | 3.084 (2) | C10···H4Bv | 3.0495 |
O3···C3i | 3.158 (3) | C10···H3Cvi | 2.9226 |
O3···F1v | 3.124 (2) | H1N···O5ii | 1.9558 |
O3···C3iv | 3.159 (3) | H1N···C10ii | 2.9187 |
O3···F1 | 2.649 (2) | H2···C2ii | 3.0528 |
O3···N2viii | 2.690 (3) | H2···O2 | 2.8327 |
O4···F2 | 2.637 (3) | H2N···C7xi | 2.6879 |
O4···N3iv | 2.958 (3) | H2N···O3xi | 1.7568 |
O4···C4viii | 3.359 (4) | H2N···H4A | 2.4719 |
O4···N3viii | 3.079 (3) | H3···F1ii | 2.8168 |
O5···N1ii | 2.796 (2) | H3···F3ix | 2.5351 |
O5···F1 | 2.862 (3) | H3···O3ix | 2.2647 |
O5···F3 | 2.696 (2) | H3A···C1 | 2.9338 |
O6···F4 | 2.622 (2) | H3A···F2x | 2.5718 |
O6···C6 | 3.310 (3) | H3A···O4x | 2.0639 |
O6···F3iii | 2.983 (2) | H3A···O1 | 2.6063 |
O6···F2 | 3.183 (3) | H3A···C7x | 2.8647 |
O6···N3vi | 2.775 (2) | H3B···H4A | 2.5015 |
O6···O2 | 2.544 (3) | H3B···F2x | 2.7065 |
O6···C5vi | 3.337 (2) | H3B···C7xi | 3.0178 |
O6···O1vi | 3.231 (2) | H3B···O4xi | 2.2185 |
O1···H5v | 2.2868 | H3C···O6vii | 1.8904 |
O1···H3C | 2.6400 | H3C···C10vii | 2.9226 |
O1···H5vi | 2.7565 | H3C···F4vii | 2.6907 |
O1···H4Av | 2.8580 | H3C···O1 | 2.6400 |
O1···H3A | 2.6063 | H4A···C2iii | 2.9183 |
O2···H4B | 2.5244 | H4A···H2N | 2.4719 |
O2···H2 | 2.8327 | H4A···O1iii | 2.8580 |
O3···H3i | 2.2647 | H4A···O4xi | 2.5791 |
O3···H2Nviii | 1.7568 | H4A···H3B | 2.5015 |
O4···H4Aviii | 2.5791 | H4B···O5iii | 2.6125 |
O4···H3Aiv | 2.0639 | H4B···O2 | 2.5244 |
O4···H3Bviii | 2.2185 | H4B···C10iii | 3.0495 |
O5···H4Bv | 2.6125 | H5···O1iii | 2.2868 |
O5···H22 | 2.74 (4) | H5···O1vii | 2.7565 |
O5···H1Nii | 1.9558 | H5···C6vii | 3.0206 |
O6···H22 | 1.63 (5) | H22···O6 | 1.63 (5) |
O6···H3Cvi | 1.8904 | H22···C10 | 2.42 (4) |
N1···N2 | 2.135 (3) | H22···F3iii | 2.78 (5) |
N1···O5ii | 2.796 (2) | H22···O5 | 2.74 (4) |
N1···F3ix | 3.083 (2) | | |
| | | |
C6—O2—H22 | 112 (3) | N2—C3—H3 | 121.55 |
C2—N1—C3 | 108.9 (2) | C1—C4—H4A | 109.62 |
C1—N2—C3 | 109.5 (2) | C1—C4—H4B | 109.40 |
C3—N1—H1N | 124.92 | C5—C4—H4A | 111.33 |
C2—N1—H1N | 125.73 | C5—C4—H4B | 107.12 |
C3—N2—H2N | 126.99 | H4A—C4—H4B | 103.76 |
C1—N2—H2N | 123.25 | N3—C5—H5 | 106.84 |
C5—N3—H3A | 111.49 | C4—C5—H5 | 105.66 |
C5—N3—H3B | 110.68 | C6—C5—H5 | 109.75 |
C5—N3—H3C | 110.75 | O3—C7—O4 | 129.3 (3) |
H3B—N3—H3C | 108.66 | O3—C7—C8 | 114.3 (2) |
H3A—N3—H3B | 106.16 | O4—C7—C8 | 116.44 (19) |
H3A—N3—H3C | 108.97 | F1—C8—F2 | 106.61 (17) |
N2—C1—C2 | 105.74 (19) | F1—C8—C7 | 109.18 (18) |
N2—C1—C4 | 121.6 (2) | F1—C8—C9 | 107.6 (2) |
C2—C1—C4 | 132.6 (2) | F2—C8—C7 | 110.9 (2) |
N1—C2—C1 | 107.4 (2) | F2—C8—C9 | 107.05 (19) |
N1—C3—N2 | 108.5 (2) | C7—C8—C9 | 115.11 (18) |
C1—C4—C5 | 114.98 (17) | F3—C9—F4 | 106.63 (16) |
C4—C5—C6 | 112.92 (17) | F3—C9—C8 | 108.04 (18) |
N3—C5—C4 | 112.7 (2) | F3—C9—C10 | 110.3 (2) |
N3—C5—C6 | 108.74 (18) | F4—C9—C8 | 107.3 (2) |
O1—C6—C5 | 122.9 (2) | F4—C9—C10 | 111.41 (18) |
O2—C6—C5 | 111.01 (18) | C8—C9—C10 | 112.95 (17) |
O1—C6—O2 | 126.1 (2) | O5—C10—O6 | 128.7 (2) |
N1—C2—H2 | 121.09 | O5—C10—C9 | 116.38 (18) |
C1—C2—H2 | 131.53 | O6—C10—C9 | 114.90 (17) |
N1—C3—H3 | 129.49 | | |
| | | |
C2—N1—C3—N2 | 0.4 (3) | O4—C7—C8—F1 | −138.9 (2) |
C3—N1—C2—C1 | −0.2 (3) | O4—C7—C8—F2 | −21.8 (3) |
C3—N2—C1—C4 | −178.21 (19) | O4—C7—C8—C9 | 99.9 (3) |
C1—N2—C3—N1 | −0.5 (3) | F1—C8—C9—F3 | −73.8 (2) |
C3—N2—C1—C2 | 0.4 (2) | F1—C8—C9—F4 | 171.54 (16) |
N2—C1—C4—C5 | −102.7 (2) | F1—C8—C9—C10 | 48.4 (2) |
C4—C1—C2—N1 | 178.2 (2) | F2—C8—C9—F3 | 171.88 (17) |
N2—C1—C2—N1 | −0.1 (2) | F2—C8—C9—F4 | 57.3 (2) |
C2—C1—C4—C5 | 79.2 (3) | F2—C8—C9—C10 | −65.9 (2) |
C1—C4—C5—N3 | 67.1 (3) | C7—C8—C9—F3 | 48.1 (2) |
C1—C4—C5—C6 | −56.6 (3) | C7—C8—C9—F4 | −66.5 (2) |
N3—C5—C6—O1 | 9.2 (3) | C7—C8—C9—C10 | 170.36 (15) |
N3—C5—C6—O2 | −171.53 (15) | F3—C9—C10—O5 | 39.5 (3) |
C4—C5—C6—O1 | 135.1 (2) | F3—C9—C10—O6 | −141.1 (2) |
C4—C5—C6—O2 | −45.7 (3) | F4—C9—C10—O5 | 157.6 (2) |
O3—C7—C8—F1 | 39.9 (3) | F4—C9—C10—O6 | −22.9 (3) |
O3—C7—C8—F2 | 157.1 (2) | C8—C9—C10—O5 | −81.5 (2) |
O3—C7—C8—C9 | −81.2 (2) | C8—C9—C10—O6 | 97.9 (2) |
Symmetry codes: (i) −x+1, y−1, −z+1; (ii) −x+1, y, −z+1; (iii) x, y+1, z; (iv) x+1/2, y−1/2, z; (v) x, y−1, z; (vi) −x+1/2, y−1/2, −z; (vii) −x+1/2, y+1/2, −z; (viii) x+1/2, y−3/2, z; (ix) −x+1, y+1, −z+1; (x) x−1/2, y+1/2, z; (xi) x−1/2, y+3/2, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O5ii | 0.85 | 1.96 | 2.796 (2) | 172 |
N2—H2N···O3xi | 0.93 | 1.76 | 2.690 (3) | 179 |
N3—H3A···O4x | 0.91 | 2.06 | 2.958 (3) | 168 |
N3—H3B···O4xi | 0.90 | 2.22 | 3.079 (3) | 160 |
N3—H3C···O6vii | 0.92 | 1.89 | 2.775 (2) | 161 |
O2—H22···O6 | 0.92 (5) | 1.63 (5) | 2.544 (3) | 171 (4) |
C3—H3···F3ix | 0.90 | 2.54 | 2.862 (2) | 102 |
C3—H3···O3ix | 0.90 | 2.26 | 3.158 (3) | 170 |
C4—H4A···O4xi | 0.97 | 2.58 | 3.359 (4) | 138 |
C5—H5···O1iii | 0.89 | 2.29 | 3.040 (3) | 142 |
Symmetry codes: (ii) −x+1, y, −z+1; (iii) x, y+1, z; (vii) −x+1/2, y+1/2, −z; (ix) −x+1, y+1, −z+1; (x) x−1/2, y+1/2, z; (xi) x−1/2, y+3/2, z. |