The title compound, (C
6H
15N
4O
2)
3·CrF
6·3H
2O, is isostructural with the vanadium analogue. One of the argininium cations is partially disordered over two different conformations. A complex network of N—H
O, N—H
F, O—H
O and O—H
F hydrogen bonds supports the structure.
Supporting information
CCDC reference: 289759
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.028
- wR factor = 0.076
- Data-to-parameter ratio = 14.2
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ....... 5
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.95
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.70 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13B
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Cr1
PLAT301_ALERT_3_C Main Residue Disorder ......................... 10.00 Perc.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10B .. F3 .. 2.60 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9H .. F3 .. 2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6A .. F2 .. 2.63 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 18.70 Deg.
C14A -C15 -C14B 1.555 1.555 1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3
C6 H15 N4 O2
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C18 H51 Cr1 F6 N12 O9
Atom count from _chemical_formula_moiety:H6 Cr1 F6 O3
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 25.48
From the CIF: _reflns_number_total 6118
Count of symmetry unique reflns 3273
Completeness (_total/calc) 186.92%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 2845
Fraction of Friedel pairs measured 0.869
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
13 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 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
6 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Tris(
L-argininium) hexafluorochromate(III) trihydrate
top
Crystal data top
(C6H15N4O2)3·CrF6·3H2O | F(000) = 786 |
Mr = 745.71 | Dx = 1.500 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 25 reflections |
a = 10.8194 (15) Å | θ = 9.8–15.7° |
b = 9.0434 (15) Å | µ = 0.44 mm−1 |
c = 16.998 (2) Å | T = 293 K |
β = 96.890 (12)° | Prism, green |
V = 1651.2 (4) Å3 | 0.34 × 0.22 × 0.15 mm |
Z = 2 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 5397 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 25.5°, θmin = 2.6° |
profile data from ω/2θ scans | h = −13→13 |
Absorption correction: ψ scan North et al. (1968) | k = −10→10 |
Tmin = 0.884, Tmax = 0.984 | l = −20→20 |
12219 measured reflections | 3 standard reflections every 180 min |
6118 independent reflections | intensity decay: 7% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difmap and geom |
R[F2 > 2σ(F2)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.076 | w = 1/[σ2(Fo2) + (0.0451P)2 + 0.3634P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
6118 reflections | Δρmax = 0.28 e Å−3 |
432 parameters | Δρmin = −0.29 e Å−3 |
1 restraint | Absolute structure: Flack (1983), with 2845 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.010 (14) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) 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 | Occ. (<1) |
O5 | 0.00167 (17) | 0.6492 (2) | 0.41979 (10) | 0.0465 (4) | |
O6 | −0.1085 (2) | 0.4836 (3) | 0.47856 (12) | 0.0616 (6) | |
N12 | 0.0364 (2) | 0.4770 (3) | 0.61211 (12) | 0.0516 (6) | |
H12A | 0.0095 | 0.3908 | 0.5915 | 0.077* | |
H12B | −0.0256 | 0.5228 | 0.6321 | 0.077* | |
H12C | 0.0987 | 0.4616 | 0.6504 | 0.077* | |
C13A | 0.5643 (6) | 0.4348 (8) | 0.4851 (4) | 0.0411 (18)* | 0.547 (4) |
N10A | 0.6384 (4) | 0.4981 (5) | 0.4407 (3) | 0.0469 (11)* | 0.547 (4) |
H10A | 0.7173 | 0.4829 | 0.4494 | 0.056* | 0.547 (4) |
H10B | 0.6085 | 0.5552 | 0.4026 | 0.056* | 0.547 (4) |
N9A | 0.6049 (5) | 0.3477 (5) | 0.5433 (3) | 0.0497 (12)* | 0.547 (4) |
H9E | 0.6833 | 0.3302 | 0.5535 | 0.060* | 0.547 (4) |
H9F | 0.5533 | 0.3074 | 0.5716 | 0.060* | 0.547 (4) |
N11A | 0.4384 (4) | 0.4313 (5) | 0.4539 (2) | 0.0449 (10)* | 0.547 (4) |
H11A | 0.4252 | 0.5018 | 0.4200 | 0.054* | 0.547 (4) |
C14A | 0.3309 (6) | 0.3592 (8) | 0.4570 (4) | 0.0542 (16)* | 0.547 (4) |
H14A | 0.3575 | 0.2665 | 0.4824 | 0.065* | 0.547 (4) |
H14B | 0.3051 | 0.3339 | 0.4020 | 0.065* | 0.547 (4) |
C13B | 0.5494 (6) | 0.4057 (7) | 0.4875 (4) | 0.0230 (16)* | 0.453 (4) |
N9B | 0.6495 (5) | 0.3976 (7) | 0.5503 (3) | 0.0445 (13)* | 0.453 (4) |
H9G | 0.7225 | 0.4279 | 0.5428 | 0.053* | 0.453 (4) |
H9H | 0.6368 | 0.3624 | 0.5956 | 0.053* | 0.453 (4) |
N10B | 0.5681 (5) | 0.4562 (6) | 0.4226 (3) | 0.0479 (13)* | 0.453 (4) |
H10C | 0.5063 | 0.4743 | 0.3872 | 0.057* | 0.453 (4) |
H10D | 0.6429 | 0.4733 | 0.4128 | 0.057* | 0.453 (4) |
N11B | 0.4417 (4) | 0.3725 (5) | 0.5133 (3) | 0.0401 (12)* | 0.453 (4) |
H11B | 0.4401 | 0.3864 | 0.5632 | 0.048* | 0.453 (4) |
C14B | 0.3474 (6) | 0.3272 (8) | 0.4794 (4) | 0.0433 (16)* | 0.453 (4) |
H14C | 0.3444 | 0.2230 | 0.4926 | 0.052* | 0.453 (4) |
H14D | 0.3572 | 0.3318 | 0.4234 | 0.052* | 0.453 (4) |
C15 | 0.2171 (3) | 0.3883 (4) | 0.4868 (2) | 0.0620 (8) | |
H15A | 0.2007 | 0.3080 | 0.5219 | 0.074* | |
H15B | 0.1513 | 0.3874 | 0.4427 | 0.074* | |
C16 | 0.2096 (3) | 0.5318 (3) | 0.53084 (17) | 0.0509 (7) | |
H16A | 0.2395 | 0.6108 | 0.4995 | 0.061* | |
H16B | 0.2647 | 0.5261 | 0.5802 | 0.061* | |
C17 | 0.0807 (2) | 0.5705 (3) | 0.54925 (14) | 0.0442 (6) | |
H17 | 0.0842 | 0.6725 | 0.5689 | 0.053* | |
C18 | −0.0194 (2) | 0.5662 (3) | 0.47653 (13) | 0.0384 (6) | |
O1 | −0.11357 (14) | 0.6287 (2) | 0.10928 (9) | 0.0409 (4) | |
O2 | −0.08743 (16) | 0.5861 (3) | −0.01584 (10) | 0.0614 (6) | |
N1 | 0.61281 (18) | 0.5439 (2) | 0.05838 (10) | 0.0336 (4) | |
H1A | 0.6866 | 0.5776 | 0.0721 | 0.040* | |
H1B | 0.5587 | 0.5454 | 0.0915 | 0.040* | |
N2 | 0.66765 (18) | 0.4887 (3) | −0.06356 (11) | 0.0378 (5) | |
H21 | 0.7411 | 0.5228 | −0.0491 | 0.045* | |
H22 | 0.6492 | 0.4538 | −0.1106 | 0.045* | |
N3 | 0.47024 (16) | 0.4362 (2) | −0.03686 (10) | 0.0318 (4) | |
H3 | 0.4564 | 0.4071 | −0.0853 | 0.038* | |
N4 | 0.12335 (15) | 0.7020 (2) | 0.15329 (10) | 0.0320 (4) | |
H4A | 0.1057 | 0.6300 | 0.1858 | 0.048* | |
H4B | 0.0792 | 0.7821 | 0.1620 | 0.048* | |
H4C | 0.2042 | 0.7231 | 0.1620 | 0.048* | |
C1 | 0.5828 (2) | 0.4900 (3) | −0.01334 (13) | 0.0273 (5) | |
C2 | 0.3682 (2) | 0.4214 (3) | 0.01062 (13) | 0.0306 (5) | |
H2A | 0.4020 | 0.3925 | 0.0638 | 0.037* | |
H2B | 0.3143 | 0.3422 | −0.0113 | 0.037* | |
C3 | 0.2897 (2) | 0.5598 (3) | 0.01601 (14) | 0.0348 (5) | |
H3A | 0.3364 | 0.6327 | 0.0492 | 0.042* | |
H3B | 0.2691 | 0.6021 | −0.0364 | 0.042* | |
C4 | 0.1713 (2) | 0.5208 (3) | 0.05074 (15) | 0.0348 (5) | |
H4D | 0.1935 | 0.4654 | 0.0992 | 0.042* | |
H4E | 0.1215 | 0.4564 | 0.0138 | 0.042* | |
C5 | 0.09122 (18) | 0.6528 (3) | 0.06922 (12) | 0.0289 (4) | |
H5 | 0.1091 | 0.7347 | 0.0346 | 0.035* | |
C6 | −0.04913 (19) | 0.6194 (3) | 0.05401 (13) | 0.0337 (5) | |
O3 | 0.04646 (15) | 0.2149 (2) | 0.28779 (11) | 0.0455 (4) | |
O4 | 0.09058 (14) | 0.43988 (19) | 0.24696 (11) | 0.0430 (4) | |
N5 | −0.66000 (19) | 0.3234 (2) | 0.23416 (14) | 0.0389 (5) | |
H5A | −0.6080 | 0.3812 | 0.2149 | 0.047* | |
H5B | −0.7319 | 0.3561 | 0.2425 | 0.047* | |
N6 | −0.71125 (19) | 0.0976 (2) | 0.27997 (14) | 0.0436 (5) | |
H6A | −0.6930 | 0.0067 | 0.2909 | 0.052* | |
H6B | −0.7828 | 0.1320 | 0.2879 | 0.052* | |
N7 | −0.52055 (17) | 0.1286 (2) | 0.23947 (13) | 0.0388 (5) | |
H7 | −0.5057 | 0.0398 | 0.2561 | 0.047* | |
N8 | −0.13067 (16) | 0.5544 (2) | 0.27264 (11) | 0.0291 (4) | |
H8A | −0.0770 | 0.6006 | 0.3082 | 0.044* | |
H8B | −0.2080 | 0.5784 | 0.2805 | 0.044* | |
H8C | −0.1172 | 0.5816 | 0.2241 | 0.044* | |
C7 | −0.62923 (19) | 0.1843 (2) | 0.25099 (13) | 0.0290 (5) | |
C8 | −0.42333 (19) | 0.1999 (3) | 0.20199 (14) | 0.0362 (5) | |
H8D | −0.4601 | 0.2759 | 0.1663 | 0.043* | |
H8E | −0.3845 | 0.1276 | 0.1707 | 0.043* | |
C9 | −0.3253 (2) | 0.2686 (3) | 0.26079 (15) | 0.0369 (6) | |
H9C | −0.3032 | 0.1998 | 0.3040 | 0.044* | |
H9D | −0.3590 | 0.3569 | 0.2827 | 0.044* | |
C10 | −0.2090 (2) | 0.3093 (3) | 0.22373 (14) | 0.0348 (5) | |
H101 | −0.2322 | 0.3708 | 0.1776 | 0.042* | |
H102 | −0.1711 | 0.2198 | 0.2061 | 0.042* | |
C11 | −0.11364 (18) | 0.3919 (2) | 0.28132 (13) | 0.0273 (4) | |
H11 | −0.1284 | 0.3651 | 0.3353 | 0.033* | |
C12 | 0.01995 (19) | 0.3477 (2) | 0.27090 (14) | 0.0296 (5) | |
Cr1 | 0.49704 (3) | 0.71574 (4) | 0.252087 (18) | 0.01879 (6) | |
F1 | 0.47150 (15) | 0.55540 (16) | 0.18108 (8) | 0.0432 (4) | |
F2 | 0.52296 (14) | 0.87441 (16) | 0.32413 (7) | 0.0389 (3) | |
F3 | 0.39670 (12) | 0.62185 (15) | 0.32183 (7) | 0.0341 (3) | |
F4 | 0.35180 (11) | 0.81164 (15) | 0.20105 (8) | 0.0343 (3) | |
F5 | 0.59500 (12) | 0.81517 (15) | 0.18282 (7) | 0.0324 (3) | |
F6 | 0.64292 (12) | 0.62530 (18) | 0.30262 (8) | 0.0433 (4) | |
O7 | 0.82415 (19) | 0.8913 (3) | 0.24899 (12) | 0.0508 (5) | |
H71 | 0.855 (4) | 0.906 (5) | 0.210 (2) | 0.076* | |
H72 | 0.748 (4) | 0.871 (5) | 0.228 (2) | 0.076* | |
O8 | 0.1745 (2) | 0.7744 (3) | 0.32883 (14) | 0.0561 (5) | |
H81 | 0.132 (4) | 0.725 (5) | 0.352 (2) | 0.084* | |
H82 | 0.222 (4) | 0.710 (5) | 0.322 (2) | 0.084* | |
O9 | 1.00848 (19) | 0.9973 (2) | 0.15416 (12) | 0.0497 (5) | |
H91 | 1.025 (3) | 1.039 (5) | 0.109 (2) | 0.075* | |
H92 | 1.034 (3) | 1.063 (5) | 0.184 (2) | 0.075* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O5 | 0.0489 (10) | 0.0535 (10) | 0.0372 (9) | 0.0038 (9) | 0.0058 (8) | 0.0030 (8) |
O6 | 0.0588 (12) | 0.0728 (14) | 0.0498 (11) | −0.0172 (11) | −0.0072 (9) | 0.0104 (10) |
N12 | 0.0485 (12) | 0.0741 (16) | 0.0317 (11) | 0.0132 (12) | 0.0027 (9) | 0.0042 (11) |
C15 | 0.0460 (15) | 0.0569 (18) | 0.080 (2) | 0.0042 (14) | −0.0052 (15) | −0.0172 (16) |
C16 | 0.0545 (16) | 0.0511 (16) | 0.0443 (15) | −0.0062 (13) | −0.0052 (12) | −0.0040 (12) |
C17 | 0.0489 (14) | 0.0510 (16) | 0.0309 (12) | 0.0087 (12) | −0.0025 (10) | −0.0057 (11) |
C18 | 0.0431 (13) | 0.0377 (13) | 0.0335 (12) | 0.0103 (11) | 0.0015 (10) | −0.0040 (10) |
O1 | 0.0250 (7) | 0.0663 (12) | 0.0323 (8) | −0.0037 (8) | 0.0067 (6) | −0.0035 (8) |
O2 | 0.0325 (9) | 0.119 (2) | 0.0320 (9) | −0.0105 (11) | 0.0018 (7) | −0.0180 (11) |
N1 | 0.0300 (9) | 0.0476 (12) | 0.0228 (9) | −0.0045 (9) | 0.0016 (7) | −0.0118 (8) |
N2 | 0.0322 (10) | 0.0537 (13) | 0.0289 (10) | −0.0067 (9) | 0.0088 (8) | −0.0153 (9) |
N3 | 0.0267 (9) | 0.0459 (11) | 0.0225 (8) | 0.0014 (8) | 0.0020 (7) | −0.0142 (8) |
N4 | 0.0260 (8) | 0.0368 (10) | 0.0326 (9) | −0.0037 (8) | 0.0007 (6) | −0.0037 (9) |
C1 | 0.0279 (11) | 0.0276 (11) | 0.0263 (11) | 0.0057 (9) | 0.0028 (8) | −0.0031 (9) |
C2 | 0.0268 (10) | 0.0351 (12) | 0.0300 (11) | 0.0010 (9) | 0.0036 (8) | −0.0069 (9) |
C3 | 0.0308 (11) | 0.0397 (13) | 0.0350 (12) | 0.0037 (10) | 0.0083 (9) | −0.0012 (10) |
C4 | 0.0302 (11) | 0.0311 (12) | 0.0443 (13) | −0.0013 (9) | 0.0092 (10) | −0.0031 (10) |
C5 | 0.0264 (10) | 0.0332 (10) | 0.0274 (10) | −0.0004 (9) | 0.0051 (8) | −0.0024 (9) |
C6 | 0.0263 (10) | 0.0440 (14) | 0.0308 (11) | −0.0019 (10) | 0.0037 (9) | −0.0036 (10) |
O3 | 0.0360 (8) | 0.0327 (8) | 0.0703 (11) | 0.0061 (8) | 0.0163 (7) | 0.0093 (10) |
O4 | 0.0270 (8) | 0.0355 (9) | 0.0692 (11) | 0.0014 (7) | 0.0173 (7) | 0.0109 (8) |
N5 | 0.0299 (9) | 0.0226 (9) | 0.0658 (14) | 0.0028 (8) | 0.0120 (9) | 0.0060 (9) |
N6 | 0.0324 (10) | 0.0259 (10) | 0.0746 (15) | 0.0010 (9) | 0.0152 (10) | 0.0084 (10) |
N7 | 0.0264 (9) | 0.0205 (10) | 0.0696 (14) | −0.0009 (7) | 0.0065 (9) | 0.0081 (9) |
N8 | 0.0240 (8) | 0.0301 (10) | 0.0337 (9) | 0.0037 (8) | 0.0052 (7) | −0.0025 (8) |
C7 | 0.0262 (10) | 0.0204 (12) | 0.0399 (12) | −0.0013 (8) | 0.0017 (9) | −0.0020 (8) |
C8 | 0.0281 (10) | 0.0350 (13) | 0.0461 (12) | −0.0007 (10) | 0.0064 (9) | −0.0016 (11) |
C9 | 0.0310 (12) | 0.0411 (13) | 0.0388 (13) | −0.0080 (10) | 0.0055 (10) | −0.0024 (10) |
C10 | 0.0290 (11) | 0.0364 (13) | 0.0389 (12) | −0.0056 (10) | 0.0045 (9) | −0.0065 (10) |
C11 | 0.0239 (9) | 0.0280 (11) | 0.0309 (10) | 0.0004 (8) | 0.0072 (8) | 0.0020 (9) |
C12 | 0.0257 (10) | 0.0298 (12) | 0.0337 (11) | 0.0020 (9) | 0.0052 (8) | −0.0010 (9) |
Cr1 | 0.02276 (13) | 0.01764 (12) | 0.01635 (12) | 0.00124 (12) | 0.00392 (9) | 0.00185 (11) |
F1 | 0.0726 (10) | 0.0280 (7) | 0.0326 (7) | −0.0156 (7) | 0.0214 (7) | −0.0103 (6) |
F2 | 0.0624 (9) | 0.0308 (7) | 0.0223 (6) | −0.0032 (7) | 0.0009 (6) | −0.0042 (5) |
F3 | 0.0355 (6) | 0.0367 (8) | 0.0322 (7) | 0.0014 (6) | 0.0131 (5) | 0.0105 (6) |
F4 | 0.0275 (6) | 0.0379 (8) | 0.0357 (7) | 0.0002 (6) | −0.0037 (5) | 0.0141 (6) |
F5 | 0.0327 (6) | 0.0405 (8) | 0.0245 (6) | −0.0065 (6) | 0.0060 (5) | 0.0106 (6) |
F6 | 0.0293 (7) | 0.0536 (9) | 0.0488 (8) | 0.0163 (7) | 0.0116 (6) | 0.0249 (7) |
O7 | 0.0422 (10) | 0.0667 (13) | 0.0422 (10) | −0.0174 (10) | 0.0000 (8) | −0.0014 (10) |
O8 | 0.0528 (12) | 0.0499 (11) | 0.0688 (14) | 0.0029 (9) | 0.0203 (10) | 0.0035 (10) |
O9 | 0.0614 (12) | 0.0497 (12) | 0.0394 (10) | −0.0072 (9) | 0.0113 (9) | −0.0006 (8) |
Geometric parameters (Å, º) top
O5—C18 | 1.264 (3) | N4—H4B | 0.8900 |
O6—C18 | 1.223 (3) | N4—H4C | 0.8900 |
N12—C17 | 1.486 (4) | C2—C3 | 1.522 (3) |
N12—H12A | 0.8900 | C2—H2A | 0.9700 |
N12—H12B | 0.8900 | C2—H2B | 0.9700 |
N12—H12C | 0.8900 | C3—C4 | 1.515 (3) |
C13A—N10A | 1.298 (8) | C3—H3A | 0.9700 |
C13A—N9A | 1.299 (8) | C3—H3B | 0.9700 |
C13A—N11A | 1.401 (7) | C4—C5 | 1.529 (3) |
N10A—H10A | 0.8600 | C4—H4D | 0.9700 |
N10A—H10B | 0.8600 | C4—H4E | 0.9700 |
N9A—H9E | 0.8600 | C5—C6 | 1.539 (3) |
N9A—H9F | 0.8600 | C5—H5 | 0.9800 |
N11A—C14A | 1.340 (7) | O3—C12 | 1.259 (3) |
N11A—H11A | 0.8600 | O4—C12 | 1.233 (3) |
C14A—C15 | 1.411 (7) | N5—C7 | 1.324 (3) |
C14A—H14A | 0.9700 | N5—H5A | 0.8600 |
C14A—H14B | 0.9700 | N5—H5B | 0.8600 |
C13B—N10B | 1.232 (8) | N6—C7 | 1.323 (3) |
C13B—N11B | 1.329 (8) | N6—H6A | 0.8600 |
C13B—N9B | 1.429 (8) | N6—H6B | 0.8600 |
N9B—H9G | 0.8600 | N7—C7 | 1.316 (3) |
N9B—H9H | 0.8600 | N7—C8 | 1.445 (3) |
N10B—H10C | 0.8600 | N7—H7 | 0.8600 |
N10B—H10D | 0.8600 | N8—C11 | 1.487 (3) |
N11B—C14B | 1.183 (8) | N8—H8A | 0.8900 |
N11B—H11B | 0.8600 | N8—H8B | 0.8900 |
C14B—C15 | 1.533 (7) | N8—H8C | 0.8900 |
C14B—H14C | 0.9700 | C8—C9 | 1.502 (3) |
C14B—H14D | 0.9700 | C8—H8D | 0.9700 |
C15—C16 | 1.505 (4) | C8—H8E | 0.9700 |
C15—H15A | 0.9700 | C9—C10 | 1.519 (3) |
C15—H15B | 0.9700 | C9—H9C | 0.9700 |
C16—C17 | 1.506 (4) | C9—H9D | 0.9700 |
C16—H16A | 0.9700 | C10—C11 | 1.529 (3) |
C16—H16B | 0.9700 | C10—H101 | 0.9700 |
C17—C18 | 1.543 (3) | C10—H102 | 0.9700 |
C17—H17 | 0.9800 | C11—C12 | 1.530 (3) |
O1—C6 | 1.238 (3) | C11—H11 | 0.9800 |
O2—C6 | 1.247 (3) | Cr1—F2 | 1.8855 (14) |
N1—C1 | 1.317 (3) | Cr1—F1 | 1.8857 (14) |
N1—H1A | 0.8600 | Cr1—F6 | 1.8902 (13) |
N1—H1B | 0.8600 | Cr1—F3 | 1.9010 (13) |
N2—C1 | 1.327 (3) | Cr1—F5 | 1.9020 (13) |
N2—H21 | 0.8600 | Cr1—F4 | 1.9096 (13) |
N2—H22 | 0.8600 | O7—H71 | 0.79 (4) |
N3—C1 | 1.327 (3) | O7—H72 | 0.88 (4) |
N3—C2 | 1.450 (3) | O8—H81 | 0.78 (4) |
N3—H3 | 0.8600 | O8—H82 | 0.79 (4) |
N4—C5 | 1.497 (3) | O9—H91 | 0.89 (4) |
N4—H4A | 0.8900 | O9—H92 | 0.80 (4) |
| | | |
C17—N12—H12A | 109.5 | N3—C2—H2B | 108.5 |
C17—N12—H12B | 109.5 | C3—C2—H2B | 108.5 |
H12A—N12—H12B | 109.5 | H2A—C2—H2B | 107.5 |
C17—N12—H12C | 109.5 | C4—C3—C2 | 109.6 (2) |
H12A—N12—H12C | 109.5 | C4—C3—H3A | 109.7 |
H12B—N12—H12C | 109.5 | C2—C3—H3A | 109.7 |
N10A—C13A—N9A | 122.3 (6) | C4—C3—H3B | 109.7 |
N10A—C13A—N11A | 115.5 (5) | C2—C3—H3B | 109.7 |
N9A—C13A—N11A | 119.9 (6) | H3A—C3—H3B | 108.2 |
C13A—N10A—H10A | 120.0 | C3—C4—C5 | 115.1 (2) |
C13A—N10A—H10B | 120.0 | C3—C4—H4D | 108.5 |
H10A—N10A—H10B | 120.0 | C5—C4—H4D | 108.5 |
C13A—N9A—H9E | 120.0 | C3—C4—H4E | 108.5 |
C13A—N9A—H9F | 120.0 | C5—C4—H4E | 108.5 |
H9E—N9A—H9F | 120.0 | H4D—C4—H4E | 107.5 |
C14A—N11A—C13A | 143.6 (6) | N4—C5—C4 | 110.83 (18) |
C14A—N11A—H11A | 108.2 | N4—C5—C6 | 109.26 (17) |
C13A—N11A—H11A | 108.2 | C4—C5—C6 | 112.59 (19) |
N11A—C14A—C15 | 136.3 (6) | N4—C5—H5 | 108.0 |
N11A—C14A—H14A | 103.1 | C4—C5—H5 | 108.0 |
C15—C14A—H14A | 103.1 | C6—C5—H5 | 108.0 |
N11A—C14A—H14B | 103.1 | O1—C6—O2 | 125.9 (2) |
C15—C14A—H14B | 103.1 | O1—C6—C5 | 119.55 (19) |
H14A—C14A—H14B | 105.1 | O2—C6—C5 | 114.56 (19) |
N10B—C13B—N11B | 128.6 (6) | C7—N5—H5A | 120.0 |
N10B—C13B—N9B | 119.8 (6) | C7—N5—H5B | 120.0 |
N11B—C13B—N9B | 111.0 (5) | H5A—N5—H5B | 120.0 |
C13B—N9B—H9G | 120.0 | C7—N6—H6A | 120.0 |
C13B—N9B—H9H | 120.0 | C7—N6—H6B | 120.0 |
H9G—N9B—H9H | 120.0 | H6A—N6—H6B | 120.0 |
C13B—N10B—H10C | 120.0 | C7—N7—C8 | 127.25 (19) |
C13B—N10B—H10D | 120.0 | C7—N7—H7 | 116.4 |
H10C—N10B—H10D | 120.0 | C8—N7—H7 | 116.4 |
C14B—N11B—C13B | 131.0 (6) | C11—N8—H8A | 109.5 |
C14B—N11B—H11B | 114.5 | C11—N8—H8B | 109.5 |
C13B—N11B—H11B | 114.5 | H8A—N8—H8B | 109.5 |
N11B—C14B—C15 | 125.6 (6) | C11—N8—H8C | 109.5 |
N11B—C14B—H14C | 105.9 | H8A—N8—H8C | 109.5 |
C15—C14B—H14C | 105.9 | H8B—N8—H8C | 109.5 |
N11B—C14B—H14D | 105.9 | N7—C7—N6 | 118.66 (19) |
C15—C14B—H14D | 105.9 | N7—C7—N5 | 122.6 (2) |
H14C—C14B—H14D | 106.2 | N6—C7—N5 | 118.8 (2) |
C14A—C15—C16 | 116.2 (4) | N7—C8—C9 | 112.6 (2) |
C14A—C15—C14B | 18.7 (3) | N7—C8—H8D | 109.1 |
C16—C15—C14B | 117.2 (3) | C9—C8—H8D | 109.1 |
C14A—C15—H15A | 108.2 | N7—C8—H8E | 109.1 |
C16—C15—H15A | 108.2 | C9—C8—H8E | 109.1 |
C14B—C15—H15A | 91.1 | H8D—C8—H8E | 107.8 |
C14A—C15—H15B | 108.2 | C8—C9—C10 | 112.2 (2) |
C16—C15—H15B | 108.2 | C8—C9—H9C | 109.2 |
C14B—C15—H15B | 122.1 | C10—C9—H9C | 109.2 |
H15A—C15—H15B | 107.4 | C8—C9—H9D | 109.2 |
C15—C16—C17 | 114.2 (2) | C10—C9—H9D | 109.2 |
C15—C16—H16A | 108.7 | H9C—C9—H9D | 107.9 |
C17—C16—H16A | 108.7 | C9—C10—C11 | 112.44 (19) |
C15—C16—H16B | 108.7 | C9—C10—H101 | 109.1 |
C17—C16—H16B | 108.7 | C11—C10—H101 | 109.1 |
H16A—C16—H16B | 107.6 | C9—C10—H102 | 109.1 |
N12—C17—C16 | 113.8 (2) | C11—C10—H102 | 109.1 |
N12—C17—C18 | 107.8 (2) | H101—C10—H102 | 107.8 |
C16—C17—C18 | 113.9 (2) | N8—C11—C10 | 110.69 (18) |
N12—C17—H17 | 107.0 | N8—C11—C12 | 110.76 (17) |
C16—C17—H17 | 107.0 | C10—C11—C12 | 111.86 (18) |
C18—C17—H17 | 107.0 | N8—C11—H11 | 107.8 |
O6—C18—O5 | 126.8 (2) | C10—C11—H11 | 107.8 |
O6—C18—C17 | 118.2 (2) | C12—C11—H11 | 107.8 |
O5—C18—C17 | 115.0 (2) | O4—C12—O3 | 125.9 (2) |
C1—N1—H1A | 120.0 | O4—C12—C11 | 119.53 (19) |
C1—N1—H1B | 120.0 | O3—C12—C11 | 114.53 (19) |
H1A—N1—H1B | 120.0 | F2—Cr1—F1 | 179.29 (7) |
C1—N2—H21 | 120.0 | F2—Cr1—F6 | 89.03 (7) |
C1—N2—H22 | 120.0 | F1—Cr1—F6 | 90.48 (7) |
H21—N2—H22 | 120.0 | F2—Cr1—F3 | 89.23 (6) |
C1—N3—C2 | 126.75 (18) | F1—Cr1—F3 | 90.28 (6) |
C1—N3—H3 | 116.6 | F6—Cr1—F3 | 91.80 (6) |
C2—N3—H3 | 116.6 | F2—Cr1—F5 | 89.53 (6) |
C5—N4—H4A | 109.5 | F1—Cr1—F5 | 90.97 (6) |
C5—N4—H4B | 109.5 | F6—Cr1—F5 | 89.37 (6) |
H4A—N4—H4B | 109.5 | F3—Cr1—F5 | 178.28 (7) |
C5—N4—H4C | 109.5 | F2—Cr1—F4 | 89.98 (7) |
H4A—N4—H4C | 109.5 | F1—Cr1—F4 | 90.52 (7) |
H4B—N4—H4C | 109.5 | F6—Cr1—F4 | 178.59 (7) |
N1—C1—N2 | 119.1 (2) | F3—Cr1—F4 | 89.19 (6) |
N1—C1—N3 | 122.0 (2) | F5—Cr1—F4 | 89.62 (6) |
N2—C1—N3 | 118.9 (2) | H71—O7—H72 | 99 (3) |
N3—C2—C3 | 115.2 (2) | H81—O8—H82 | 94 (4) |
N3—C2—H2A | 108.5 | H91—O9—H92 | 98 (4) |
C3—C2—H2A | 108.5 | | |
| | | |
N10A—C13A—N11A—C14A | 156.5 (7) | C1—N3—C2—C3 | 84.0 (3) |
N9A—C13A—N11A—C14A | −6.6 (12) | N3—C2—C3—C4 | 167.26 (18) |
C13A—N11A—C14A—C15 | 108.3 (10) | C2—C3—C4—C5 | 172.63 (19) |
N10B—C13B—N11B—C14B | 33.2 (12) | C3—C4—C5—N4 | −92.8 (2) |
N9B—C13B—N11B—C14B | −156.0 (7) | C3—C4—C5—C6 | 144.5 (2) |
C13B—N11B—C14B—C15 | −132.6 (7) | N4—C5—C6—O1 | −3.4 (3) |
N11A—C14A—C15—C16 | −4.1 (10) | C4—C5—C6—O1 | 120.2 (2) |
N11A—C14A—C15—C14B | −101.9 (17) | N4—C5—C6—O2 | 175.8 (2) |
N11B—C14B—C15—C14A | 101.7 (17) | C4—C5—C6—O2 | −60.6 (3) |
N11B—C14B—C15—C16 | 10.0 (9) | C8—N7—C7—N6 | 173.9 (2) |
C14A—C15—C16—C17 | 170.1 (4) | C8—N7—C7—N5 | −5.6 (4) |
C14B—C15—C16—C17 | −169.0 (4) | C7—N7—C8—C9 | 96.4 (3) |
C15—C16—C17—N12 | 72.1 (3) | N7—C8—C9—C10 | 165.9 (2) |
C15—C16—C17—C18 | −52.0 (4) | C8—C9—C10—C11 | 174.8 (2) |
N12—C17—C18—O6 | −5.5 (3) | C9—C10—C11—N8 | −93.1 (2) |
C16—C17—C18—O6 | 121.8 (3) | C9—C10—C11—C12 | 142.9 (2) |
N12—C17—C18—O5 | 175.4 (2) | N8—C11—C12—O4 | −9.7 (3) |
C16—C17—C18—O5 | −57.3 (3) | C10—C11—C12—O4 | 114.3 (2) |
C2—N3—C1—N1 | −3.1 (4) | N8—C11—C12—O3 | 171.0 (2) |
C2—N3—C1—N2 | 176.6 (2) | C10—C11—C12—O3 | −65.0 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N12—H12A···O5i | 0.89 | 2.20 | 3.034 (3) | 157 |
N12—H12B···O3ii | 0.89 | 2.23 | 2.948 (3) | 137 |
N12—H12C···O7iii | 0.89 | 1.92 | 2.756 (3) | 156 |
N10A—H10B···F6 | 0.86 | 1.89 | 2.620 (5) | 141 |
N10A—H10B···F3 | 0.86 | 2.60 | 3.302 (5) | 140 |
N10B—H10D···F6 | 0.86 | 2.32 | 2.748 (6) | 111 |
N10B—H10C···F3 | 0.86 | 2.03 | 2.803 (6) | 150 |
N10A—H10A···O6iv | 0.86 | 1.89 | 2.740 (5) | 169 |
N11B—H11B···F2iii | 0.86 | 1.91 | 2.744 (5) | 163 |
N11A—H11A···F3 | 0.86 | 1.98 | 2.823 (4) | 165 |
N9A—H9E···O8iii | 0.86 | 2.43 | 3.102 (5) | 136 |
N9B—H9H···O8iii | 0.86 | 2.41 | 2.855 (6) | 113 |
N9B—H9G···O6iv | 0.86 | 2.29 | 3.117 (6) | 160 |
N9A—H9F···F2iii | 0.86 | 2.13 | 2.793 (5) | 133 |
N9B—H9H···F2iii | 0.86 | 2.33 | 3.006 (6) | 136 |
N9A—H9F···F3iii | 0.86 | 2.48 | 3.072 (5) | 127 |
N9B—H9H···F3iii | 0.86 | 2.64 | 3.384 (6) | 146 |
N1—H1A···O1iv | 0.86 | 2.23 | 3.080 (2) | 171 |
N1—H1B···F1 | 0.86 | 1.89 | 2.732 (2) | 167 |
N2—H21···O2iv | 0.86 | 1.96 | 2.818 (3) | 176 |
N2—H22···F4v | 0.86 | 2.00 | 2.820 (2) | 158 |
N3—H3···F5v | 0.86 | 1.88 | 2.726 (2) | 168 |
N4—H4A···O4 | 0.89 | 2.03 | 2.901 (3) | 168 |
N4—H4B···O9vi | 0.89 | 2.09 | 2.946 (3) | 161 |
N4—H4C···F4 | 0.89 | 1.84 | 2.696 (2) | 161 |
N5—H5B···O4vi | 0.86 | 2.07 | 2.929 (3) | 173 |
N5—H5A···F1vi | 0.86 | 1.92 | 2.747 (2) | 162 |
N6—H6A···F4vii | 0.86 | 2.42 | 3.028 (3) | 128 |
N6—H6A···F2vii | 0.86 | 2.63 | 3.256 (3) | 131 |
N6—H6B···O3vi | 0.86 | 1.99 | 2.846 (3) | 171 |
N7—H7···F2vii | 0.86 | 1.89 | 2.723 (2) | 162 |
N8—H8A···O5 | 0.89 | 2.03 | 2.860 (3) | 154 |
N8—H8B···F6vi | 0.89 | 1.75 | 2.640 (2) | 176 |
N8—H8C···O1 | 0.89 | 2.00 | 2.884 (2) | 171 |
O7—H71···O9 | 0.79 (4) | 2.17 (4) | 2.875 (3) | 148 (4) |
O7—H72···F5 | 0.88 (4) | 1.81 (4) | 2.687 (2) | 175 (4) |
O8—H81···O5 | 0.78 (4) | 2.05 (4) | 2.804 (3) | 165 (5) |
O8—H82···F3 | 0.79 (4) | 2.06 (4) | 2.787 (3) | 154 (4) |
O9—H91···O2viii | 0.89 (4) | 1.85 (4) | 2.718 (3) | 166 (4) |
O9—H92···O3ix | 0.80 (4) | 2.23 (4) | 2.996 (3) | 160 (4) |
Symmetry codes: (i) −x, y−1/2, −z+1; (ii) −x, y+1/2, −z+1; (iii) −x+1, y−1/2, −z+1; (iv) x+1, y, z; (v) −x+1, y−1/2, −z; (vi) x−1, y, z; (vii) x−1, y−1, z; (viii) −x+1, y+1/2, −z; (ix) x+1, y+1, z. |