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The title molecule, C
10H
14F
6N
2O
2, possesses a crystallographically imposed centre of symmetry. In the crystal structure, intermolecular N—H
O hydrogen bonds link the molecules into two-dimensional crimped layers parallel to the
bc plane.
Supporting information
CCDC reference: 624192
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.060
- wR factor = 0.157
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.63 mm
PLAT213_ALERT_2_C Atom F2 has ADP max/min Ratio ............. 3.40 prola
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C5
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.40
PLAT301_ALERT_3_C Main Residue Disorder ......................... 23.00 Perc.
PLAT431_ALERT_2_C Short Inter HL..A Contact F2 .. O1 .. 2.94 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 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
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
N,
N'-Bis(2,2,2-trifluoroacetyl)hexane-1,6-diamine
top
Crystal data top
C10H14F6N2O2 | F(000) = 316 |
Mr = 308.23 | Dx = 1.511 Mg m−3 |
Monoclinic, P21/c | Melting point: 403.2 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 7.2009 (14) Å | Cell parameters from 5297 reflections |
b = 10.498 (2) Å | θ = 3.4–27.5° |
c = 8.9607 (18) Å | µ = 0.16 mm−1 |
β = 90.51 (3)° | T = 296 K |
V = 677.4 (2) Å3 | Block, colourless |
Z = 2 | 0.63 × 0.60 × 0.21 mm |
Data collection top
Rigaku R-AXIS RAPID IP diffractometer | 1544 independent reflections |
Radiation source: rotating anode | 1298 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
ω scans | θmax = 27.5°, θmin = 3.4° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −9→9 |
Tmin = 0.907, Tmax = 0.968 | k = −13→13 |
6508 measured reflections | l = −11→11 |
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)] = 0.060 | H-atom parameters constrained |
wR(F2) = 0.157 | w = 1/[σ2(Fo2) + (0.0583P)2 + 0.4876P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.005 |
1544 reflections | Δρmax = 0.41 e Å−3 |
103 parameters | Δρmin = −0.33 e Å−3 |
30 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.13 (2) |
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) |
F1 | 1.4120 (2) | 0.1436 (2) | 0.5701 (3) | 0.1077 (11) | 0.906 (4) |
F2 | 1.2537 (4) | 0.1375 (3) | 0.3734 (2) | 0.1524 (19) | 0.906 (4) |
F3 | 1.2395 (3) | −0.01080 (17) | 0.5285 (3) | 0.0984 (10) | 0.906 (4) |
F1A | 1.3610 (16) | 0.0416 (11) | 0.5939 (13) | 0.066 (4)* | 0.094 (4) |
F2A | 1.3534 (17) | 0.1975 (10) | 0.4499 (15) | 0.066 (4)* | 0.094 (4) |
F3A | 1.1829 (19) | 0.0407 (11) | 0.4093 (11) | 0.066 (4)* | 0.094 (4) |
O1 | 1.0702 (2) | 0.14462 (17) | 0.72761 (17) | 0.0574 (5) | |
N1 | 1.0016 (2) | 0.26638 (18) | 0.52643 (18) | 0.0447 (5) | |
H1A | 1.0312 | 0.2841 | 0.4360 | 0.054* | |
C1 | 0.5659 (3) | 0.4697 (2) | 0.5555 (2) | 0.0489 (6) | |
H1B | 0.4964 | 0.4122 | 0.6188 | 0.059* | |
H1C | 0.6186 | 0.5357 | 0.6187 | 0.059* | |
C2 | 0.7228 (3) | 0.3963 (2) | 0.4829 (2) | 0.0486 (6) | |
H2A | 0.6708 | 0.3312 | 0.4180 | 0.058* | |
H2B | 0.7950 | 0.4539 | 0.4219 | 0.058* | |
C3 | 0.8479 (3) | 0.3347 (2) | 0.5965 (2) | 0.0504 (6) | |
H3A | 0.8976 | 0.3996 | 0.6628 | 0.061* | |
H3B | 0.7762 | 0.2756 | 0.6560 | 0.061* | |
C4 | 1.0946 (3) | 0.1787 (2) | 0.5993 (2) | 0.0415 (5) | |
C5 | 1.2507 (3) | 0.11244 (18) | 0.5144 (2) | 0.0549 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.0419 (10) | 0.116 (2) | 0.166 (3) | −0.0002 (10) | 0.0151 (12) | −0.0385 (17) |
F2 | 0.183 (3) | 0.218 (4) | 0.0574 (12) | 0.145 (3) | 0.0544 (15) | 0.0335 (16) |
F3 | 0.0947 (16) | 0.0541 (11) | 0.147 (2) | 0.0160 (10) | 0.0330 (14) | −0.0219 (12) |
O1 | 0.0658 (11) | 0.0653 (11) | 0.0413 (9) | 0.0145 (8) | 0.0057 (7) | 0.0053 (7) |
N1 | 0.0439 (9) | 0.0516 (10) | 0.0387 (9) | 0.0106 (7) | 0.0091 (7) | 0.0026 (7) |
C1 | 0.0435 (11) | 0.0556 (13) | 0.0476 (11) | 0.0100 (9) | 0.0030 (9) | −0.0039 (10) |
C2 | 0.0432 (11) | 0.0562 (13) | 0.0465 (11) | 0.0094 (9) | 0.0053 (9) | −0.0005 (9) |
C3 | 0.0474 (12) | 0.0596 (13) | 0.0443 (11) | 0.0157 (10) | 0.0080 (9) | −0.0026 (10) |
C4 | 0.0411 (10) | 0.0440 (11) | 0.0393 (10) | 0.0030 (8) | 0.0025 (8) | −0.0037 (8) |
C5 | 0.0516 (13) | 0.0580 (14) | 0.0555 (13) | 0.0145 (10) | 0.0096 (10) | −0.0010 (11) |
Geometric parameters (Å, º) top
F1—C5 | 1.302 (2) | C1—C1i | 1.510 (4) |
F2—C5 | 1.291 (2) | C1—C2 | 1.519 (3) |
F3—C5 | 1.302 (2) | C1—H1B | 0.9700 |
F1A—C5 | 1.297 (3) | C1—H1C | 0.9700 |
F2A—C5 | 1.298 (3) | C2—C3 | 1.500 (3) |
F3A—C5 | 1.298 (3) | C2—H2A | 0.9700 |
O1—C4 | 1.219 (3) | C2—H2B | 0.9700 |
N1—C4 | 1.309 (3) | C3—H3A | 0.9700 |
N1—C3 | 1.465 (3) | C3—H3B | 0.9700 |
N1—H1A | 0.8600 | C4—C5 | 1.530 (3) |
| | | |
C4—N1—C3 | 121.05 (17) | N1—C4—C5 | 116.54 (17) |
C4—N1—H1A | 119.5 | F2—C5—F1A | 129.7 (7) |
C3—N1—H1A | 119.5 | F2—C5—F3A | 54.4 (6) |
C1i—C1—C2 | 113.4 (2) | F1A—C5—F3A | 106.9 (3) |
C1i—C1—H1B | 108.9 | F2—C5—F2A | 53.8 (6) |
C2—C1—H1B | 108.9 | F1A—C5—F2A | 106.9 (3) |
C1i—C1—H1C | 108.9 | F3A—C5—F2A | 106.8 (3) |
C2—C1—H1C | 108.9 | F2—C5—F3 | 107.39 (19) |
H1B—C1—H1C | 107.7 | F1A—C5—F3 | 54.2 (6) |
C3—C2—C1 | 111.85 (18) | F3A—C5—F3 | 58.1 (6) |
C3—C2—H2A | 109.2 | F2A—C5—F3 | 139.7 (7) |
C1—C2—H2A | 109.2 | F2—C5—F1 | 107.50 (19) |
C3—C2—H2B | 109.2 | F1A—C5—F1 | 52.7 (6) |
C1—C2—H2B | 109.2 | F3A—C5—F1 | 138.8 (7) |
H2A—C2—H2B | 107.9 | F2A—C5—F1 | 59.2 (6) |
N1—C3—C2 | 111.81 (18) | F3—C5—F1 | 105.54 (17) |
N1—C3—H3A | 109.3 | F2—C5—C4 | 114.40 (18) |
C2—C3—H3A | 109.3 | F1A—C5—C4 | 115.9 (7) |
N1—C3—H3B | 109.3 | F3A—C5—C4 | 110.6 (7) |
C2—C3—H3B | 109.3 | F2A—C5—C4 | 109.4 (7) |
H3A—C3—H3B | 107.9 | F3—C5—C4 | 110.93 (18) |
O1—C4—N1 | 126.83 (19) | F1—C5—C4 | 110.62 (18) |
O1—C4—C5 | 116.63 (18) | | |
| | | |
C1i—C1—C2—C3 | −178.6 (2) | O1—C4—C5—F3A | 111.0 (7) |
C4—N1—C3—C2 | −160.8 (2) | N1—C4—C5—F3A | −69.2 (7) |
C1—C2—C3—N1 | −178.70 (19) | O1—C4—C5—F2A | −131.6 (7) |
C3—N1—C4—O1 | −0.9 (4) | N1—C4—C5—F2A | 48.2 (7) |
C3—N1—C4—C5 | 179.28 (18) | O1—C4—C5—F3 | 48.5 (3) |
O1—C4—C5—F2 | 170.2 (2) | N1—C4—C5—F3 | −131.7 (2) |
N1—C4—C5—F2 | −10.0 (3) | O1—C4—C5—F1 | −68.2 (3) |
O1—C4—C5—F1A | −10.7 (7) | N1—C4—C5—F1 | 111.6 (2) |
N1—C4—C5—F1A | 169.1 (7) | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1ii | 0.86 | 2.03 | 2.883 (2) | 169 |
Symmetry code: (ii) x, −y+1/2, z−1/2. |
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