



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314616010105/su4055sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2414314616010105/su4055Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314616010105/su4055Isup3.cml |
CCDC reference: 1486919
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.005 Å
- R factor = 0.065
- wR factor = 0.245
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.2 Note PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.6 Note PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.005 Ang. PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 3.176 Check PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 20 Report
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details found in the CIF Please Do ! PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large 0.14 Report PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note) 0.003 Degree PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 3 Note PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2014 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 6 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density 1 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 5 ALERT level C = Check. Ensure it is not caused by an omission or oversight 8 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: Due to the collabration between two Universities involving synthesis, collecting data and structure solution. |
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
C6H10N3O+·C2F3O2− | Z = 2 |
Mr = 253.19 | F(000) = 260 |
Triclinic, P1 | Dx = 1.557 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 4.8087 (2) Å | Cell parameters from 2385 reflections |
b = 11.0283 (5) Å | θ = 2.3–28.6° |
c = 11.1135 (5) Å | µ = 0.15 mm−1 |
α = 108.704 (3)° | T = 100 K |
β = 96.174 (3)° | Plate, colourless |
γ = 100.533 (3)° | 0.37 × 0.21 × 0.07 mm |
V = 540.03 (4) Å3 |
Bruker SMART APEXII CCD area-detector diffractometer | 2467 independent reflections |
Radiation source: fine-focus sealed tube | 1674 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.060 |
φ and ω scans | θmax = 27.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −6→6 |
Tmin = 0.946, Tmax = 0.989 | k = −14→14 |
8256 measured reflections | l = −14→14 |
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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.245 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.1439P)2 + 0.1968P] where P = (Fo2 + 2Fc2)/3 |
2467 reflections | (Δ/σ)max < 0.001 |
168 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat operating at 100.0 (1) K. |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.4551 (4) | 1.1091 (2) | 0.17382 (19) | 0.0228 (5) | |
N1 | 1.1022 (5) | 1.0528 (2) | 0.2807 (2) | 0.0167 (5) | |
N2 | 0.7855 (5) | 0.8428 (2) | 0.1855 (2) | 0.0163 (5) | |
N3 | 0.7455 (6) | 0.9851 (3) | 0.3832 (2) | 0.0195 (6) | |
C1 | 1.2280 (6) | 1.0222 (3) | 0.1804 (3) | 0.0158 (6) | |
C2 | 1.1430 (6) | 0.9018 (3) | 0.0739 (3) | 0.0179 (6) | |
H2A | 1.2385 | 0.8853 | 0.0017 | 0.021* | |
C3 | 0.9158 (6) | 0.8112 (3) | 0.0812 (3) | 0.0171 (6) | |
C4 | 0.8787 (6) | 0.9604 (3) | 0.2842 (2) | 0.0147 (6) | |
C5 | 1.5516 (7) | 1.2318 (3) | 0.2847 (3) | 0.0251 (7) | |
H5A | 1.7297 | 1.2834 | 0.2738 | 0.038* | |
H5B | 1.5865 | 1.2115 | 0.3639 | 0.038* | |
H5C | 1.4031 | 1.2825 | 0.2907 | 0.038* | |
C6 | 0.7968 (7) | 0.6779 (3) | −0.0186 (3) | 0.0230 (7) | |
H6A | 0.5868 | 0.6619 | −0.0380 | 0.035* | |
H6B | 0.8501 | 0.6110 | 0.0140 | 0.035* | |
H6C | 0.8753 | 0.6731 | −0.0974 | 0.035* | |
F1 | 0.1552 (5) | 0.49986 (19) | 0.3587 (2) | 0.0416 (6) | |
F2 | −0.1411 (5) | 0.6237 (2) | 0.4158 (2) | 0.0436 (6) | |
F3 | −0.1740 (4) | 0.50887 (18) | 0.21656 (18) | 0.0311 (5) | |
O2 | 0.3283 (4) | 0.66321 (19) | 0.20575 (18) | 0.0214 (5) | |
O3 | 0.2727 (5) | 0.8038 (2) | 0.39445 (19) | 0.0243 (5) | |
C7 | 0.0153 (7) | 0.5820 (3) | 0.3252 (3) | 0.0223 (7) | |
C8 | 0.2262 (6) | 0.6949 (3) | 0.3065 (3) | 0.0159 (6) | |
H1N3 | 0.807 (7) | 1.059 (4) | 0.446 (4) | 0.022 (8)* | |
H2N3 | 0.592 (9) | 0.925 (4) | 0.385 (4) | 0.035 (10)* | |
H1N2 | 0.628 (8) | 0.792 (4) | 0.197 (3) | 0.023 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0223 (11) | 0.0158 (11) | 0.0236 (11) | −0.0036 (8) | 0.0021 (9) | 0.0031 (9) |
N1 | 0.0157 (12) | 0.0118 (11) | 0.0180 (11) | 0.0001 (9) | −0.0016 (9) | 0.0020 (9) |
N2 | 0.0177 (13) | 0.0098 (11) | 0.0156 (11) | 0.0005 (9) | −0.0003 (9) | −0.0010 (9) |
N3 | 0.0196 (13) | 0.0110 (12) | 0.0194 (12) | −0.0012 (10) | 0.0021 (10) | −0.0034 (10) |
C1 | 0.0147 (14) | 0.0122 (13) | 0.0190 (13) | 0.0029 (11) | −0.0009 (10) | 0.0049 (11) |
C2 | 0.0174 (14) | 0.0161 (14) | 0.0161 (13) | 0.0017 (11) | −0.0003 (11) | 0.0024 (11) |
C3 | 0.0159 (14) | 0.0160 (14) | 0.0150 (12) | 0.0021 (11) | −0.0024 (10) | 0.0020 (11) |
C4 | 0.0154 (13) | 0.0111 (13) | 0.0155 (12) | 0.0035 (10) | −0.0015 (10) | 0.0027 (10) |
C5 | 0.0221 (16) | 0.0120 (14) | 0.0332 (16) | −0.0043 (11) | −0.0017 (13) | 0.0039 (12) |
C6 | 0.0294 (17) | 0.0128 (14) | 0.0177 (13) | 0.0001 (12) | −0.0007 (12) | −0.0027 (11) |
F1 | 0.0434 (13) | 0.0260 (11) | 0.0592 (14) | 0.0030 (9) | −0.0028 (10) | 0.0266 (10) |
F2 | 0.0482 (14) | 0.0313 (11) | 0.0390 (12) | −0.0079 (10) | 0.0241 (10) | 0.0000 (9) |
F3 | 0.0276 (11) | 0.0195 (9) | 0.0308 (10) | −0.0099 (8) | −0.0033 (8) | −0.0007 (8) |
O2 | 0.0251 (12) | 0.0133 (10) | 0.0187 (10) | −0.0016 (8) | 0.0035 (8) | −0.0006 (8) |
O3 | 0.0291 (12) | 0.0107 (10) | 0.0226 (11) | −0.0026 (8) | 0.0057 (9) | −0.0045 (8) |
C7 | 0.0225 (15) | 0.0172 (15) | 0.0206 (14) | −0.0018 (12) | 0.0019 (12) | 0.0022 (12) |
C8 | 0.0158 (14) | 0.0085 (12) | 0.0186 (13) | −0.0004 (10) | −0.0033 (10) | 0.0019 (10) |
O1—C1 | 1.340 (3) | C3—C6 | 1.493 (4) |
O1—C5 | 1.464 (4) | C5—H5A | 0.9800 |
N1—C1 | 1.305 (3) | C5—H5B | 0.9800 |
N1—C4 | 1.353 (3) | C5—H5C | 0.9800 |
N2—C3 | 1.354 (3) | C6—H6A | 0.9800 |
N2—C4 | 1.362 (3) | C6—H6B | 0.9800 |
N2—H1N2 | 0.90 (4) | C6—H6C | 0.9800 |
N3—C4 | 1.311 (3) | F1—C7 | 1.341 (4) |
N3—H1N3 | 0.86 (4) | F2—C7 | 1.335 (3) |
N3—H2N3 | 0.90 (4) | F3—C7 | 1.344 (3) |
C1—C2 | 1.422 (4) | O2—C8 | 1.244 (3) |
C2—C3 | 1.368 (4) | O3—C8 | 1.244 (3) |
C2—H2A | 0.9500 | C7—C8 | 1.540 (4) |
C1—O1—C5 | 116.5 (2) | O1—C5—H5B | 109.5 |
C1—N1—C4 | 116.7 (2) | H5A—C5—H5B | 109.5 |
C3—N2—C4 | 121.9 (2) | O1—C5—H5C | 109.5 |
C3—N2—H1N2 | 125 (2) | H5A—C5—H5C | 109.5 |
C4—N2—H1N2 | 113 (2) | H5B—C5—H5C | 109.5 |
C4—N3—H1N3 | 119 (2) | C3—C6—H6A | 109.5 |
C4—N3—H2N3 | 120 (2) | C3—C6—H6B | 109.5 |
H1N3—N3—H2N3 | 121 (3) | H6A—C6—H6B | 109.5 |
N1—C1—O1 | 119.1 (2) | C3—C6—H6C | 109.5 |
N1—C1—C2 | 125.2 (3) | H6A—C6—H6C | 109.5 |
O1—C1—C2 | 115.7 (2) | H6B—C6—H6C | 109.5 |
C3—C2—C1 | 116.1 (2) | F2—C7—F1 | 107.4 (2) |
C3—C2—H2A | 121.9 | F2—C7—F3 | 106.1 (2) |
C1—C2—H2A | 121.9 | F1—C7—F3 | 106.5 (2) |
N2—C3—C2 | 118.7 (2) | F2—C7—C8 | 113.2 (2) |
N2—C3—C6 | 116.6 (2) | F1—C7—C8 | 111.1 (2) |
C2—C3—C6 | 124.7 (2) | F3—C7—C8 | 112.1 (2) |
N3—C4—N1 | 119.5 (2) | O2—C8—O3 | 129.4 (2) |
N3—C4—N2 | 119.2 (3) | O2—C8—C7 | 114.8 (2) |
N1—C4—N2 | 121.3 (2) | O3—C8—C7 | 115.8 (2) |
O1—C5—H5A | 109.5 | ||
C4—N1—C1—O1 | −178.3 (2) | C1—N1—C4—N3 | 179.4 (3) |
C4—N1—C1—C2 | 2.0 (4) | C1—N1—C4—N2 | −1.9 (4) |
C5—O1—C1—N1 | 2.3 (4) | C3—N2—C4—N3 | −179.4 (3) |
C5—O1—C1—C2 | −178.0 (2) | C3—N2—C4—N1 | 1.8 (4) |
N1—C1—C2—C3 | −1.9 (4) | F2—C7—C8—O2 | −164.9 (3) |
O1—C1—C2—C3 | 178.4 (2) | F1—C7—C8—O2 | 74.2 (3) |
C4—N2—C3—C2 | −1.7 (4) | F3—C7—C8—O2 | −44.9 (4) |
C4—N2—C3—C6 | 178.6 (2) | F2—C7—C8—O3 | 16.0 (4) |
C1—C2—C3—N2 | 1.6 (4) | F1—C7—C8—O3 | −105.0 (3) |
C1—C2—C3—C6 | −178.7 (3) | F3—C7—C8—O3 | 135.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H1N3···O3i | 0.86 (4) | 2.05 (4) | 2.822 (3) | 148 (3) |
N3—H2N3···O3 | 0.90 (4) | 1.88 (5) | 2.782 (4) | 178 (5) |
N2—H1N2···O2 | 0.90 (4) | 1.86 (4) | 2.758 (3) | 170 (4) |
C2—H2A···O1ii | 0.95 | 2.58 | 3.514 (4) | 168 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+3, −y+2, −z. |