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Neutralization of 4-[(2,2,3,3-tetrafluoropropoxy)methyl]pyridine with hydrohalo acids H
X (
X = Cl and Br) yielded the pyridinium salts 4-[(2,2,3,3-tetrafluoropropoxy)methyl]pyridinium chloride, C
9H
10F
4NO
+·Cl
−, (1), and 4-[(2,2,3,3-tetrafluoropropoxy)methyl]pyridinium bromide, C
9H
10F
4NO
+·Br
−, (2), both carrying a fluorous side chain at the
para position of the pyridinium ring. Single-crystal X-ray diffraction techniques revealed that (1) and (2) are isomorphous. The halide anions accept four hydrogen bonds from N—H,
ortho-C—H and CF
2—H groups. Two cations and two anions form a centrosymmetric dimeric building block, utilizing complimentary N—H
XH—C
sp3 connections. These dimers are further crosslinked, utilizing another complimentary C
sp2—H
XH—C
sp2 connection. The pyridinium rings are π-stacked, forming columns running parallel to the
a axis that make angles of
ca 44–45° with the normal to the pyridinium plane. There are also supramolecular C—H
F—C interactions, namely bifurcated C—H
F and bifurcated C—F
H interactions; additionally, one type II C—F
F—C halogen bond has been observed.
Supporting information
CCDC references: 1537616; 1537615
For both compounds, data collection: APEX2 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a). Program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015b) and SIR92 (Altomare et al., 1993) for i16197; SHELXL2013 (Sheldrick, 2015b) for i16318. Molecular graphics: shelXle (Hübschle et al., 2011) for i16197; shelXle (Hübschle et al., 2011) and for i16318. Software used to prepare material for publication: SHELXTL (Sheldrick, 2008) for i16197; WinGX (Farrugia, 2012) for i16318.
(i16197) 4-[(2,2,3,3-Tetrafluoropropoxy)methyl]pyridinium chloride
top
Crystal data top
C9H10F4NO+·Cl− | F(000) = 528 |
Mr = 259.63 | Dx = 1.610 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 4.7874 (4) Å | Cell parameters from 2075 reflections |
b = 8.2086 (6) Å | θ = 2.6–27.1° |
c = 27.2894 (18) Å | µ = 0.39 mm−1 |
β = 92.803 (4)° | T = 100 K |
V = 1071.13 (14) Å3 | Plate, colourless |
Z = 4 | 0.32 × 0.30 × 0.02 mm |
Data collection top
Bruker APEXII CCD diffractometer | 2007 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.064 |
Absorption correction: multi-scan (SADABS; Bruker, 1996) | θmax = 27.1°, θmin = 2.6° |
Tmin = 0.875, Tmax = 0.971 | h = −6→6 |
31900 measured reflections | k = −10→10 |
2356 independent reflections | l = −34→34 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.031 | All H-atom parameters refined |
wR(F2) = 0.071 | w = 1/[σ2(Fo2) + (0.0275P)2 + 0.541P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.002 |
2356 reflections | Δρmax = 0.33 e Å−3 |
185 parameters | Δρmin = −0.25 e Å−3 |
Special details top
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. The diffraction data were collected at 100 (1) K, employing a
Bruker CCD diffractometer SMART (Bruker, 2001); the refinement was performed
with the SHELXL-2013 program package (Sheldrick, 2015). Cell refinement:
SMART; absorption correction: SADABS (Sheldrick, 2015); data reduction: SAINT
(Bruker, 2001); program(s) used to solve structure: SIR92 (Altomare et
al., 1993); program(s) used to refine structure: molecular graphics:
ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for
publication: WinGX (Farrugia, 2012). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 1.06998 (8) | 0.23740 (4) | 0.54207 (2) | 0.01628 (11) | |
F1 | −0.41306 (18) | 0.71203 (11) | 0.25298 (3) | 0.0192 (2) | |
F2 | 0.03030 (19) | 0.70185 (13) | 0.27420 (3) | 0.0251 (2) | |
F3 | −0.5332 (2) | 0.77524 (13) | 0.34747 (4) | 0.0291 (3) | |
F4 | −0.2340 (3) | 0.94451 (12) | 0.31776 (4) | 0.0396 (3) | |
O1 | −0.0587 (2) | 0.46628 (12) | 0.34176 (4) | 0.0181 (3) | |
N1 | 0.6283 (3) | 0.23528 (16) | 0.46065 (5) | 0.0152 (3) | |
C1 | 0.4980 (3) | 0.10408 (19) | 0.44159 (5) | 0.0165 (3) | |
C2 | 0.2848 (3) | 0.12348 (19) | 0.40664 (5) | 0.0146 (3) | |
C3 | 0.2051 (3) | 0.27954 (18) | 0.39149 (5) | 0.0116 (3) | |
C4 | 0.3417 (3) | 0.41255 (19) | 0.41306 (5) | 0.0134 (3) | |
C5 | 0.5562 (3) | 0.3868 (2) | 0.44760 (5) | 0.0151 (3) | |
C6 | −0.0204 (3) | 0.29861 (18) | 0.35182 (5) | 0.0128 (3) | |
C7 | −0.2588 (3) | 0.49700 (19) | 0.30287 (5) | 0.0148 (3) | |
C8 | −0.2283 (3) | 0.67391 (19) | 0.29078 (5) | 0.0143 (3) | |
C9 | −0.2666 (4) | 0.78916 (19) | 0.33344 (6) | 0.0194 (4) | |
H1 | 0.566 (3) | 0.001 (2) | 0.4526 (6) | 0.016 (4)* | |
H1A | 0.762 (4) | 0.224 (2) | 0.4819 (7) | 0.028 (5)* | |
H2 | 0.196 (3) | 0.031 (2) | 0.3934 (6) | 0.017 (4)* | |
H4 | 0.294 (3) | 0.516 (2) | 0.4043 (6) | 0.013 (4)* | |
H5 | 0.662 (3) | 0.472 (2) | 0.4628 (6) | 0.016 (4)* | |
H6A | 0.032 (3) | 0.243 (2) | 0.3220 (6) | 0.015 (4)* | |
H6B | −0.191 (4) | 0.250 (2) | 0.3620 (6) | 0.013 (4)* | |
H7A | −0.446 (4) | 0.476 (2) | 0.3124 (6) | 0.017 (4)* | |
H7B | −0.219 (3) | 0.435 (2) | 0.2737 (6) | 0.017 (4)* | |
H9 | −0.140 (4) | 0.769 (2) | 0.3610 (6) | 0.015 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0179 (2) | 0.01525 (19) | 0.01528 (18) | 0.00206 (15) | −0.00332 (13) | −0.00042 (14) |
F1 | 0.0186 (5) | 0.0230 (5) | 0.0153 (4) | 0.0031 (4) | −0.0055 (4) | 0.0053 (4) |
F2 | 0.0141 (5) | 0.0362 (6) | 0.0250 (5) | −0.0048 (4) | 0.0023 (4) | 0.0116 (4) |
F3 | 0.0267 (6) | 0.0338 (6) | 0.0270 (5) | 0.0082 (5) | 0.0026 (4) | −0.0106 (4) |
F4 | 0.0646 (8) | 0.0112 (5) | 0.0414 (6) | −0.0043 (5) | −0.0122 (5) | 0.0038 (4) |
O1 | 0.0242 (6) | 0.0099 (5) | 0.0189 (5) | 0.0010 (5) | −0.0120 (4) | 0.0010 (4) |
N1 | 0.0127 (7) | 0.0211 (7) | 0.0116 (6) | 0.0026 (5) | 0.0000 (5) | 0.0014 (5) |
C1 | 0.0192 (8) | 0.0142 (8) | 0.0165 (7) | 0.0044 (6) | 0.0040 (6) | 0.0040 (6) |
C2 | 0.0169 (8) | 0.0121 (7) | 0.0148 (7) | −0.0008 (6) | 0.0024 (6) | −0.0003 (6) |
C3 | 0.0110 (7) | 0.0142 (7) | 0.0099 (6) | 0.0010 (6) | 0.0043 (5) | 0.0001 (5) |
C4 | 0.0169 (8) | 0.0111 (8) | 0.0125 (7) | 0.0013 (6) | 0.0028 (6) | 0.0007 (6) |
C5 | 0.0159 (8) | 0.0171 (8) | 0.0125 (7) | −0.0015 (6) | 0.0028 (6) | −0.0023 (6) |
C6 | 0.0157 (8) | 0.0098 (7) | 0.0130 (7) | −0.0005 (6) | 0.0001 (6) | 0.0002 (6) |
C7 | 0.0148 (8) | 0.0153 (8) | 0.0137 (7) | 0.0003 (6) | −0.0043 (6) | −0.0002 (6) |
C8 | 0.0099 (7) | 0.0197 (8) | 0.0129 (7) | −0.0009 (6) | −0.0029 (6) | 0.0049 (6) |
C9 | 0.0243 (9) | 0.0113 (8) | 0.0221 (8) | −0.0006 (7) | −0.0053 (7) | 0.0018 (6) |
Geometric parameters (Å, º) top
F1—C8 | 1.3621 (15) | C3—C4 | 1.389 (2) |
F2—C8 | 1.3581 (17) | C3—C6 | 1.499 (2) |
F3—C9 | 1.355 (2) | C4—C5 | 1.376 (2) |
F4—C9 | 1.3565 (18) | C4—H4 | 0.907 (18) |
O1—C6 | 1.4137 (18) | C5—H5 | 0.949 (17) |
O1—C7 | 1.4171 (17) | C6—H6A | 0.976 (17) |
N1—C5 | 1.334 (2) | C6—H6B | 0.963 (17) |
N1—C1 | 1.337 (2) | C7—C8 | 1.498 (2) |
N1—H1A | 0.85 (2) | C7—H7A | 0.962 (17) |
C1—C2 | 1.372 (2) | C7—H7B | 0.970 (17) |
C1—H1 | 0.954 (18) | C8—C9 | 1.518 (2) |
C2—C3 | 1.394 (2) | C9—H9 | 0.957 (18) |
C2—H2 | 0.933 (18) | | |
| | | |
C6—O1—C7 | 113.28 (11) | O1—C6—H6B | 110.8 (10) |
C5—N1—C1 | 122.50 (14) | C3—C6—H6B | 109.8 (10) |
C5—N1—H1A | 117.3 (13) | H6A—C6—H6B | 107.8 (14) |
C1—N1—H1A | 120.3 (13) | O1—C7—C8 | 105.53 (12) |
N1—C1—C2 | 119.61 (15) | O1—C7—H7A | 111.9 (10) |
N1—C1—H1 | 116.6 (10) | C8—C7—H7A | 109.4 (10) |
C2—C1—H1 | 123.7 (10) | O1—C7—H7B | 111.7 (10) |
C1—C2—C3 | 119.77 (15) | C8—C7—H7B | 107.6 (10) |
C1—C2—H2 | 119.0 (10) | H7A—C7—H7B | 110.5 (14) |
C3—C2—H2 | 121.2 (10) | F2—C8—F1 | 106.12 (11) |
C4—C3—C2 | 118.72 (13) | F2—C8—C7 | 109.72 (13) |
C4—C3—C6 | 122.10 (13) | F1—C8—C7 | 108.83 (12) |
C2—C3—C6 | 119.16 (13) | F2—C8—C9 | 107.26 (13) |
C5—C4—C3 | 119.32 (14) | F1—C8—C9 | 109.82 (12) |
C5—C4—H4 | 119.6 (10) | C7—C8—C9 | 114.73 (13) |
C3—C4—H4 | 121.1 (10) | F3—C9—F4 | 107.04 (13) |
N1—C5—C4 | 120.05 (14) | F3—C9—C8 | 108.37 (12) |
N1—C5—H5 | 116.6 (10) | F4—C9—C8 | 108.90 (13) |
C4—C5—H5 | 123.3 (10) | F3—C9—H9 | 109.6 (10) |
O1—C6—C3 | 108.90 (12) | F4—C9—H9 | 109.2 (10) |
O1—C6—H6A | 109.3 (10) | C8—C9—H9 | 113.5 (10) |
C3—C6—H6A | 110.3 (10) | | |
(i16318) 4-[(2,2,3,3-Tetrafluoropropoxy)methyl]pyridinium bromide
top
Crystal data top
C9H10F4NO+·Br− | F(000) = 600 |
Mr = 304.09 | Dx = 1.828 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 4.7977 (3) Å | Cell parameters from 6743 reflections |
b = 8.3123 (6) Å | θ = 2.9–27.1° |
c = 27.739 (2) Å | µ = 3.75 mm−1 |
β = 92.646 (3)° | T = 100 K |
V = 1105.04 (13) Å3 | Niddle, colourless |
Z = 4 | 0.36 × 0.08 × 0.06 mm |
Data collection top
Bruker APEXII CCD diffractometer | 2166 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.041 |
Absorption correction: multi-scan (SADABS; Bruker, 1996) | θmax = 27.1°, θmin = 2.6° |
Tmin = 0.735, Tmax = 0.971 | h = −6→6 |
21424 measured reflections | k = −10→10 |
2446 independent reflections | l = −33→35 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.021 | All H-atom parameters refined |
wR(F2) = 0.047 | w = 1/[σ2(Fo2) + (0.0179P)2 + 0.7397P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.003 |
2446 reflections | Δρmax = 0.39 e Å−3 |
185 parameters | Δρmin = −0.31 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.4699 (4) | 0.1025 (2) | 0.43760 (7) | 0.0173 (4) | |
C2 | 0.2618 (4) | 0.1251 (2) | 0.40283 (6) | 0.0145 (4) | |
C3 | 0.1886 (3) | 0.2801 (2) | 0.38822 (6) | 0.0116 (3) | |
C4 | 0.3268 (4) | 0.4105 (2) | 0.41008 (6) | 0.0136 (4) | |
C5 | 0.5350 (4) | 0.3818 (2) | 0.44457 (6) | 0.0155 (4) | |
C6 | −0.0345 (4) | 0.3020 (2) | 0.34910 (6) | 0.0127 (3) | |
C7 | −0.2648 (4) | 0.4990 (2) | 0.30097 (6) | 0.0146 (4) | |
C8 | −0.2301 (3) | 0.6737 (2) | 0.28885 (6) | 0.0141 (4) | |
C9 | −0.2679 (4) | 0.7886 (2) | 0.33060 (7) | 0.0202 (4) | |
N1 | 0.6027 (3) | 0.23085 (18) | 0.45707 (5) | 0.0155 (3) | |
O1 | −0.0669 (3) | 0.46736 (14) | 0.33916 (5) | 0.0184 (3) | |
F1 | −0.4116 (2) | 0.71197 (13) | 0.25147 (4) | 0.0191 (2) | |
F2 | 0.0300 (2) | 0.69929 (14) | 0.27276 (4) | 0.0251 (3) | |
F3 | −0.5340 (3) | 0.77647 (15) | 0.34442 (4) | 0.0315 (3) | |
F4 | −0.2321 (3) | 0.94153 (14) | 0.31507 (5) | 0.0407 (3) | |
Br1 | 1.06227 (4) | 0.23738 (2) | 0.54243 (2) | 0.01457 (6) | |
H1 | 0.529 (4) | 0.001 (2) | 0.4487 (7) | 0.015 (5)* | |
H1A | 0.732 (5) | 0.217 (3) | 0.4777 (8) | 0.025 (6)* | |
H2 | 0.174 (4) | 0.035 (2) | 0.3897 (7) | 0.014 (5)* | |
H4 | 0.280 (4) | 0.517 (2) | 0.4020 (6) | 0.011 (5)* | |
H5 | 0.640 (4) | 0.463 (2) | 0.4591 (7) | 0.012 (5)* | |
H6A | 0.019 (4) | 0.245 (2) | 0.3201 (8) | 0.017 (5)* | |
H6B | −0.209 (4) | 0.256 (2) | 0.3581 (7) | 0.015 (5)* | |
H7A | −0.457 (4) | 0.479 (2) | 0.3110 (7) | 0.011 (5)* | |
H7B | −0.232 (4) | 0.437 (2) | 0.2725 (7) | 0.014 (5)* | |
H9 | −0.145 (4) | 0.767 (2) | 0.3576 (8) | 0.016 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0204 (10) | 0.0138 (9) | 0.0179 (9) | 0.0032 (7) | 0.0034 (8) | 0.0046 (7) |
C2 | 0.0155 (9) | 0.0117 (8) | 0.0163 (9) | −0.0001 (7) | 0.0012 (7) | 0.0004 (7) |
C3 | 0.0113 (8) | 0.0139 (8) | 0.0097 (8) | 0.0016 (6) | 0.0034 (6) | −0.0006 (6) |
C4 | 0.0162 (9) | 0.0112 (8) | 0.0136 (9) | 0.0006 (7) | 0.0034 (7) | 0.0006 (7) |
C5 | 0.0158 (9) | 0.0172 (9) | 0.0137 (9) | −0.0025 (7) | 0.0023 (7) | −0.0018 (7) |
C6 | 0.0144 (9) | 0.0093 (8) | 0.0144 (9) | 0.0007 (7) | −0.0003 (7) | −0.0005 (7) |
C7 | 0.0166 (10) | 0.0145 (9) | 0.0123 (9) | 0.0000 (7) | −0.0042 (7) | −0.0004 (7) |
C8 | 0.0099 (8) | 0.0195 (9) | 0.0126 (8) | −0.0012 (7) | −0.0028 (7) | 0.0050 (7) |
C9 | 0.0263 (11) | 0.0128 (9) | 0.0210 (10) | 0.0001 (8) | −0.0054 (8) | 0.0003 (7) |
N1 | 0.0121 (8) | 0.0222 (8) | 0.0122 (7) | 0.0032 (6) | −0.0003 (6) | 0.0036 (6) |
O1 | 0.0250 (7) | 0.0100 (6) | 0.0190 (7) | 0.0003 (5) | −0.0119 (5) | 0.0008 (5) |
F1 | 0.0189 (6) | 0.0233 (6) | 0.0145 (5) | 0.0028 (4) | −0.0059 (4) | 0.0052 (4) |
F2 | 0.0142 (5) | 0.0362 (7) | 0.0248 (6) | −0.0050 (5) | 0.0015 (4) | 0.0112 (5) |
F3 | 0.0284 (7) | 0.0369 (7) | 0.0292 (7) | 0.0083 (5) | 0.0027 (5) | −0.0117 (5) |
F4 | 0.0679 (9) | 0.0116 (6) | 0.0408 (8) | −0.0033 (6) | −0.0158 (7) | 0.0034 (5) |
Br1 | 0.01588 (10) | 0.01375 (9) | 0.01384 (9) | 0.00135 (7) | −0.00178 (6) | 0.00000 (7) |
Geometric parameters (Å, º) top
C1—N1 | 1.343 (2) | C6—H6B | 0.97 (2) |
C1—C2 | 1.369 (3) | C7—O1 | 1.414 (2) |
C1—H1 | 0.94 (2) | C7—C8 | 1.502 (2) |
C2—C3 | 1.391 (2) | C7—H7A | 0.989 (18) |
C2—H2 | 0.92 (2) | C7—H7B | 0.96 (2) |
C3—C4 | 1.394 (2) | C8—F1 | 1.3605 (19) |
C3—C6 | 1.500 (2) | C8—F2 | 1.361 (2) |
C4—C5 | 1.372 (3) | C8—C9 | 1.518 (3) |
C4—H4 | 0.939 (19) | C9—F3 | 1.354 (2) |
C5—N1 | 1.338 (2) | C9—F4 | 1.356 (2) |
C5—H5 | 0.92 (2) | C9—H9 | 0.95 (2) |
C6—O1 | 1.409 (2) | N1—H1A | 0.83 (2) |
C6—H6A | 0.98 (2) | | |
| | | |
N1—C1—C2 | 119.46 (17) | O1—C7—H7A | 111.0 (11) |
N1—C1—H1 | 116.7 (12) | C8—C7—H7A | 110.1 (11) |
C2—C1—H1 | 123.8 (12) | O1—C7—H7B | 112.7 (11) |
C1—C2—C3 | 119.89 (17) | C8—C7—H7B | 107.9 (11) |
C1—C2—H2 | 118.1 (12) | H7A—C7—H7B | 109.4 (15) |
C3—C2—H2 | 122.0 (12) | F1—C8—F2 | 106.13 (13) |
C2—C3—C4 | 118.98 (16) | F1—C8—C7 | 108.85 (14) |
C2—C3—C6 | 119.03 (15) | F2—C8—C7 | 109.72 (15) |
C4—C3—C6 | 121.98 (15) | F1—C8—C9 | 109.84 (15) |
C5—C4—C3 | 118.99 (17) | F2—C8—C9 | 107.18 (15) |
C5—C4—H4 | 119.3 (11) | C7—C8—C9 | 114.77 (15) |
C3—C4—H4 | 121.7 (11) | F3—C9—F4 | 107.13 (16) |
N1—C5—C4 | 120.27 (17) | F3—C9—C8 | 108.46 (15) |
N1—C5—H5 | 116.8 (12) | F4—C9—C8 | 109.03 (16) |
C4—C5—H5 | 122.9 (12) | F3—C9—H9 | 108.9 (13) |
O1—C6—C3 | 109.18 (14) | F4—C9—H9 | 110.0 (12) |
O1—C6—H6A | 110.1 (11) | C8—C9—H9 | 113.1 (12) |
C3—C6—H6A | 109.3 (12) | C5—N1—C1 | 122.38 (16) |
O1—C6—H6B | 110.4 (11) | C5—N1—H1A | 118.0 (15) |
C3—C6—H6B | 111.3 (12) | C1—N1—H1A | 119.6 (15) |
H6A—C6—H6B | 106.5 (16) | C6—O1—C7 | 113.08 (13) |
O1—C7—C8 | 105.66 (14) | | |
Hydrogen-bond geometry for (1) and (2) (Å, °) topSalt | D—H···A | Symmetry code | D—H | H···A | D···A | D—H···A |
(1) | N1—H1A···Cl1 | | 0.85 (2) | 2.16 (2) | 2.992 (2) | 168 (2) |
| C1—H1···Cl1 | -x+2, -y, -z+1 | 0.95 (2) | 2.72 (2) | 3.571 (2) | 150 (1) |
| C5—H5···Cl1 | -x+2, -y+1, -z+1 | 0.95 (2) | 2.62 (2) | 3.499 (2) | 154 (1) |
| C9—H9···Cl1 | -x+1, -y+1, -z+1 | 0.96 (2) | 2.65 (2) | 3.487 (2) | 146 (2) |
| C2—H4···O1* | | 0.91 (2) | 2.38 (2) | 2.700 (2) | 100 (1) |
(2) | N1—H1A···Br1 | | 0.83 (2) | 2.35 (2) | 3.161 (2) | 166 (2) |
| C1—H1···Br1 | -x+2, -y, -z+1 | 0.94 (2) | 2.79 (2) | 3.635 (2) | 150 (2) |
| C5—H5···Br1 | -x+2, -y+1, -z+1 | 0.92 (2) | 2.87 (2) | 3.717 (2) | 153 (2) |
| C9—H9···Br1 | -x+1, -y+1, -z+1 | 0.95 (2) | 2.78 (2) | 3.620 (2) | 148 (2) |
| C4—H4···O1* | | 0.94 (2) | 2.39 (2) | 2.705 (2) | 99 (2) |
Note: (*) intramolecular hydrogen bond. |
C—H···F—C and C—F···F—C weak interactions for (1) and (2) (Å, °) topSalt | D—H(F)···A | Symmetry code | D—H(F) | H(F)···A | D···A | D—H(F)···A |
(1) | C6—H6A···F2 | -x, y-1/2, -z+1/2 | 0.98 (2) | 2.65 (2) | 3.528 (2) | 149 (1) |
| C7—H7B···F1 | -x-1, y+1/2, -z+1/2 | 0.97 (2) | 2.62 (2) | 3.167 (2) | 116 (1) |
| C7—H7B···F2 | -x, y-1/2, -z+1/2 | 0.97 (2) | 2.51 (2) | 3.423 (2) | 156 (1) |
| C8—F1···F2 | x-1, y, z | 1.362 (2) | 2.756 (1) | 3.563 (2) | 115.6 (1) |
| C8—F2···F1 | x+1, y, z | 1.358 (2) | 2.756 (1) | 4.097 (2) | 169.0 (1) |
| C8—F2···F3 | x+1, y, z | 1.358 (2) | 2.884 (1) | 3.695 (2) | 116.5 (1) |
| C9—F3···F2 | x-1, y, z | 1.355 (2) | 2.884 (1) | 3.732 (2) | 118.8 (1) |
(2) | C6—H6A···F2 | -x, y-1/2, -z+1/2 | 0.98 (2) | 2.60 (2) | 3.487 (2) | 150 (2) |
| C7—H7B···F1 | -x-1, y+1/2, -z+1/2 | 0.96 (2) | 2.60 (2) | 3.164 (2) | 118 (1) |
| C7—H7B···F2 | -x, y-1/2, -z+1/2 | 0.96 (2) | 2.56 (2) | 3.445 (2) | 154 (2) |
| C8—F1···F2 | x-1, y, z | 1.361 (2) | 2.772 (1) | 3.564 (2) | 114.8 (1) |
| C8—F2···F1 | x+1, y, z | 1.361 (2) | 2.772 (1) | 4.120 (1) | 170.2 (1) |
| C8—F2···F3 | x+1, y, z | 1.361 (2) | 2.890 (2) | 3.713 (1) | 117.0 (1) |
| C9—F3···F2 | x-1, y, z | 1.354 (2) | 2.890 (2) | 3.738 (1) | 118.9 (1) |
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