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At low temperatures the organic salt adamantan-1-ammonium 4-fluorobenzoate, C
10H
18N
+·C
7H
4FO
2−, possesses an incommensurately modulated crystal structure. The effect of the modulation on the atomic arrangement and intermolecular interactions is studied by analysing single-crystal X-ray diffraction data within the (3 + 1)-dimensional superspace approach and superspace group
P2
1/
n(α0γ)00. The modulation strongly affects the position of the atoms as well as their atomic displacement parameters. Nevertheless, the molecular cations and anions are built by rigid moieties, which vary their orientation with respect to each other as a function of the phase of the modulation
t. Cations and anions are connected into slabs by dense N—H
O and C—H
F hydrogen-bonded networks, which are characterized by being rather rigid and which show only a little variation as a function of the phase of the modulation
t.
Supporting information
B-IncStrDB reference: 9672EtfncG
CCDC reference: 995840
Crystal data top
C17H22FNO2 | V = 1498.06 (3) Å3 |
Mr = 291.4 | Z = 4 |
Monoclinic, P21/n(α0γ)00† | F(000) = 624 |
q = 0.423700a* + 0.428400c* | Dx = 1.291 Mg m−3 |
a = 10.8498 (1) Å | Cu Kα radiation, λ = 1.5418 Å |
b = 6.5247 (1) Å | µ = 0.75 mm−1 |
c = 21.3826 (3) Å | T = 97 K |
β = 98.246 (1)° | 0.80 × 0.02 × 0.02 mm |
† Symmetry operations: (1) x1, x2, x3, x4; (2) −x1+1/2, x2+1/2, −x3+1/2, −x4; (3) −x1, −x2, −x3, −x4; (4) x1+1/2, −x2+1/2, x3+1/2, x4.
|
Data collection top
Oxford Diffraction CCD diffractometer | 6001 reflections with I > 3σ(I) |
Radiation source: X-ray tube | Rint = 0.033 |
Graphite monochromator | θmax = 65.7°, θmin = 3.5° |
Absorption correction: empirical ? | h = −12→12 |
Tmin = ?, Tmax = ? | k = −7→3 |
29463 measured reflections | l = −25→25 |
11225 independent reflections | |
Refinement top
Refinement on F | 307 constraints |
R[F2 > 2σ(F2)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.071 | Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.000121F2) |
S = 1.76 | (Δ/σ)max = 0.003 |
11225 reflections | Δρmax = 0.26 e Å−3 |
991 parameters | Δρmin = −0.27 e Å−3 |
6 restraints | |
Crystal data top
C17H22FNO2 | β = 98.246 (1)° |
Mr = 291.4 | V = 1498.06 (3) Å3 |
Monoclinic, P21/n(α0γ)00† | Z = 4 |
q = 0.423700a* + 0.428400c* | Cu Kα radiation |
a = 10.8498 (1) Å | µ = 0.75 mm−1 |
b = 6.5247 (1) Å | T = 97 K |
c = 21.3826 (3) Å | 0.80 × 0.02 × 0.02 mm |
† Symmetry operations: (1) x1, x2, x3, x4; (2) −x1+1/2, x2+1/2, −x3+1/2, −x4; (3) −x1, −x2, −x3, −x4; (4) x1+1/2, −x2+1/2, x3+1/2, x4.
|
Data collection top
Oxford Diffraction CCD diffractometer | 11225 independent reflections |
Absorption correction: empirical ? | 6001 reflections with I > 3σ(I) |
Tmin = ?, Tmax = ? | Rint = 0.033 |
29463 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.051 | 6 restraints |
wR(F2) = 0.071 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.76 | Δρmax = 0.26 e Å−3 |
11225 reflections | Δρmin = −0.27 e Å−3 |
991 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C01 | −0.06259 (9) | 0.38058 (15) | −0.15316 (6) | 0.0306 (3) | |
C02 | 0.02518 (9) | 0.29051 (15) | −0.09876 (5) | 0.0310 (3) | |
C03 | 0.09126 (11) | 0.41989 (16) | −0.05531 (6) | 0.0390 (4) | |
C04 | 0.17229 (11) | 0.34689 (17) | −0.00443 (6) | 0.0428 (4) | |
C05 | 0.18623 (11) | 0.14257 (17) | 0.00211 (6) | 0.0420 (4) | |
C06 | 0.12363 (16) | 0.00717 (19) | −0.03990 (8) | 0.0523 (5) | |
C07 | 0.04147 (13) | 0.08249 (17) | −0.09034 (6) | 0.0423 (4) | |
F08 | 0.26562 (8) | 0.06883 (11) | 0.05162 (4) | 0.0608 (3) | |
O09 | −0.12359 (7) | 0.26017 (11) | −0.19206 (4) | 0.0375 (3) | |
O10 | −0.06978 (8) | 0.57222 (12) | −0.15579 (4) | 0.0418 (3) | |
N11 | 0.14166 (8) | 0.13244 (13) | 0.24462 (4) | 0.0317 (3) | |
C12 | 0.05548 (9) | 0.13331 (13) | 0.29297 (5) | 0.0285 (3) | |
C13 | 0.09251 (10) | −0.03906 (13) | 0.34078 (5) | 0.0331 (3) | |
C14 | 0.00475 (11) | −0.03839 (14) | 0.39012 (6) | 0.0372 (4) | |
C15 | 0.01334 (10) | 0.16851 (14) | 0.42492 (6) | 0.0355 (3) | |
C16 | −0.02291 (9) | 0.34135 (13) | 0.37675 (5) | 0.0322 (3) | |
C17 | 0.06498 (9) | 0.34024 (13) | 0.32721 (5) | 0.0307 (3) | |
C18 | −0.07819 (9) | 0.09895 (13) | 0.26048 (5) | 0.0307 (3) | |
C19 | −0.16604 (9) | 0.10039 (14) | 0.30998 (6) | 0.0349 (3) | |
C20 | −0.15685 (10) | 0.30724 (14) | 0.34471 (6) | 0.0351 (3) | |
C21 | −0.12916 (11) | −0.07209 (14) | 0.35808 (6) | 0.0385 (4) | |
H03 | 0.080475 | 0.563804 | −0.060677 | 0.0468* | |
H04 | 0.217471 | 0.43786 | 0.025433 | 0.0514* | |
H06 | 0.136534 | −0.136056 | −0.034428 | 0.0627* | |
H07 | −0.004502 | −0.009952 | −0.119586 | 0.0507* | |
H11a | 0.2175 (10) | 0.1501 (13) | 0.2626 (6) | 0.0476* | |
H11b | 0.1354 (10) | 0.0108 (15) | 0.2242 (5) | 0.0476* | |
H11c | 0.1202 (11) | 0.2339 (14) | 0.2166 (5) | 0.0476* | |
H13a | 0.08697 | −0.168485 | 0.319235 | 0.0398* | |
H13b | 0.176266 | −0.017357 | 0.361068 | 0.0398* | |
H14 | 0.028077 | −0.146646 | 0.419828 | 0.0446* | |
H15a | −0.042676 | 0.168648 | 0.455798 | 0.0425* | |
H15b | 0.097066 | 0.18964 | 0.445341 | 0.0425* | |
H16 | −0.016901 | 0.471243 | 0.398035 | 0.0387* | |
H17a | 0.148861 | 0.360879 | 0.347481 | 0.0368* | |
H17b | 0.042131 | 0.44794 | 0.297245 | 0.0368* | |
H18a | −0.101038 | 0.206473 | 0.23045 | 0.0369* | |
H18b | −0.083604 | −0.030917 | 0.239188 | 0.0369* | |
H19 | −0.249823 | 0.079757 | 0.289558 | 0.0419* | |
H20a | −0.180233 | 0.415363 | 0.314982 | 0.0421* | |
H20b | −0.211836 | 0.307131 | 0.37607 | 0.0421* | |
H21a | −0.184235 | −0.07108 | 0.389397 | 0.0462* | |
H21b | −0.135038 | −0.201758 | 0.336676 | 0.0462* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C01 | 0.0232 (5) | 0.0433 (6) | 0.0247 (7) | 0.0005 (3) | 0.0019 (4) | 0.0020 (4) |
C02 | 0.0230 (5) | 0.0467 (6) | 0.0234 (7) | −0.0027 (4) | 0.0032 (4) | 0.0014 (4) |
C03 | 0.0354 (6) | 0.0436 (6) | 0.0348 (8) | 0.0074 (4) | −0.0057 (5) | −0.0057 (4) |
C04 | 0.0354 (6) | 0.0522 (6) | 0.0364 (8) | 0.0020 (4) | −0.0101 (5) | −0.0082 (5) |
C05 | 0.0367 (6) | 0.0543 (6) | 0.0314 (8) | −0.0051 (5) | −0.0080 (5) | 0.0120 (5) |
C06 | 0.0618 (11) | 0.0448 (6) | 0.0443 (9) | −0.0158 (7) | −0.0125 (8) | 0.0165 (6) |
C07 | 0.0453 (8) | 0.0439 (6) | 0.0338 (8) | −0.0171 (6) | −0.0077 (6) | 0.0076 (5) |
F08 | 0.0613 (5) | 0.0646 (4) | 0.0465 (5) | −0.0057 (3) | −0.0260 (4) | 0.0175 (3) |
O09 | 0.0274 (4) | 0.0536 (4) | 0.0284 (5) | 0.0009 (3) | −0.0064 (3) | −0.0047 (3) |
O10 | 0.0420 (4) | 0.0496 (5) | 0.0302 (5) | 0.0002 (3) | −0.0074 (3) | 0.0048 (3) |
N11 | 0.0233 (4) | 0.0460 (5) | 0.0238 (5) | 0.0006 (3) | −0.0038 (3) | 0.0024 (4) |
C12 | 0.0251 (5) | 0.0360 (5) | 0.0229 (6) | 0.0030 (3) | −0.0012 (4) | 0.0020 (4) |
C13 | 0.0328 (5) | 0.0378 (5) | 0.0274 (7) | 0.0083 (4) | −0.0009 (4) | 0.0020 (4) |
C14 | 0.0441 (6) | 0.0351 (5) | 0.0318 (7) | 0.0075 (4) | 0.0039 (5) | 0.0087 (4) |
C15 | 0.0372 (6) | 0.0447 (5) | 0.0241 (6) | 0.0063 (4) | 0.0029 (4) | 0.0021 (4) |
C16 | 0.0344 (5) | 0.0337 (4) | 0.0273 (6) | 0.0039 (3) | −0.0002 (4) | −0.0014 (4) |
C17 | 0.0275 (5) | 0.0348 (5) | 0.0273 (6) | 0.0003 (3) | −0.0040 (4) | 0.0023 (4) |
C18 | 0.0252 (5) | 0.0369 (5) | 0.0280 (6) | 0.0010 (3) | −0.0031 (4) | 0.0003 (4) |
C19 | 0.0243 (5) | 0.0434 (5) | 0.0357 (7) | −0.0003 (3) | −0.0002 (4) | −0.0016 (4) |
C20 | 0.0303 (5) | 0.0381 (5) | 0.0363 (7) | 0.0064 (3) | 0.0023 (4) | 0.0011 (4) |
C21 | 0.0412 (6) | 0.0353 (5) | 0.0408 (8) | −0.0026 (4) | 0.0119 (5) | 0.0013 (4) |
Geometric parameters (Å, º) top | Average | Minimum | Maximum |
C01—C02 | 1.513 (5) | 1.498 (5) | 1.528 (5) |
C01—O09 | 1.261 (4) | 1.239 (5) | 1.280 (4) |
C01—O10 | 1.254 (4) | 1.236 (4) | 1.268 (4) |
C02—C03 | 1.386 (5) | 1.365 (5) | 1.405 (5) |
C02—C07 | 1.388 (5) | 1.368 (5) | 1.406 (5) |
C03—C04 | 1.382 (6) | 1.371 (6) | 1.393 (6) |
C04—C05 | 1.360 (5) | 1.344 (5) | 1.380 (5) |
C05—C06 | 1.378 (6) | 1.356 (6) | 1.402 (6) |
C05—F08 | 1.355 (5) | 1.346 (5) | 1.365 (5) |
C06—C07 | 1.388 (6) | 1.380 (7) | 1.397 (6) |
N11—C12 | 1.491 (5) | 1.479 (5) | 1.499 (5) |
C12—C13 | 1.535 (4) | 1.528 (4) | 1.540 (4) |
C12—C17 | 1.533 (4) | 1.520 (4) | 1.548 (4) |
C12—C18 | 1.533 (4) | 1.526 (4) | 1.542 (4) |
C13—C14 | 1.520 (5) | 1.513 (5) | 1.527 (5) |
C14—C15 | 1.538 (4) | 1.527 (4) | 1.551 (4) |
C14—C21 | 1.531 (5) | 1.524 (5) | 1.535 (5) |
C15—C16 | 1.541 (5) | 1.535 (5) | 1.547 (4) |
C16—C17 | 1.525 (5) | 1.518 (5) | 1.531 (5) |
C16—C20 | 1.532 (5) | 1.521 (5) | 1.544 (5) |
C18—C19 | 1.524 (5) | 1.515 (5) | 1.532 (5) |
C19—C20 | 1.537 (4) | 1.516 (4) | 1.558 (4) |
C19—C21 | 1.539 (5) | 1.530 (5) | 1.548 (5) |
| | | |
C02—C01—O09 | 118.6 (3) | 117.0 (3) | 119.7 (3) |
C02—C01—O10 | 116.8 (3) | 116.0 (3) | 117.7 (3) |
O09—C01—O10 | 124.7 (3) | 123.9 (3) | 125.5 (4) |
C01—C02—C03 | 119.1 (3) | 118.1 (3) | 119.7 (3) |
C01—C02—C07 | 122.4 (3) | 121.7 (3) | 123.1 (3) |
C03—C02—C07 | 118.5 (3) | 117.8 (4) | 119.4 (3) |
C02—C03—C04 | 121.6 (3) | 120.9 (3) | 122.3 (3) |
C03—C04—C05 | 118.1 (4) | 117.4 (4) | 118.9 (4) |
C04—C05—C06 | 122.6 (4) | 121.4 (4) | 124.1 (4) |
C04—C05—F08 | 118.9 (4) | 118.1 (4) | 119.4 (4) |
C06—C05—F08 | 118.5 (3) | 117.6 (4) | 119.4 (3) |
C05—C06—C07 | 118.5 (4) | 117.5 (4) | 119.7 (3) |
C02—C07—C06 | 120.5 (4) | 120.1 (4) | 120.8 (4) |
N11—C12—C13 | 109.2 (3) | 108.8 (3) | 109.5 (3) |
N11—C12—C17 | 109.2 (3) | 108.9 (3) | 109.5 (3) |
N11—C12—C18 | 109.4 (3) | 108.5 (3) | 110.2 (3) |
C13—C12—C17 | 109.6 (3) | 109.1 (3) | 110.2 (3) |
C13—C12—C18 | 109.6 (2) | 109.1 (3) | 110.0 (2) |
C17—C12—C18 | 109.9 (2) | 109.4 (2) | 110.4 (3) |
C12—C13—C14 | 109.3 (3) | 109.1 (3) | 109.6 (3) |
C13—C14—C15 | 109.8 (3) | 109.6 (3) | 110.0 (3) |
C13—C14—C21 | 109.8 (3) | 109.4 (3) | 110.1 (3) |
C15—C14—C21 | 109.3 (3) | 108.6 (3) | 109.7 (3) |
C14—C15—C16 | 109.1 (3) | 108.4 (3) | 109.9 (3) |
C15—C16—C17 | 109.6 (3) | 109.4 (3) | 109.9 (3) |
C15—C16—C20 | 109.1 (3) | 108.8 (3) | 109.3 (3) |
C17—C16—C20 | 109.7 (3) | 109.5 (3) | 110.0 (3) |
C12—C17—C16 | 109.3 (3) | 109.0 (3) | 109.7 (3) |
C12—C18—C19 | 109.3 (3) | 108.8 (3) | 109.7 (3) |
C18—C19—C20 | 109.7 (3) | 109.5 (3) | 110.1 (3) |
C18—C19—C21 | 109.4 (3) | 109.0 (3) | 109.6 (3) |
C20—C19—C21 | 109.1 (3) | 108.4 (3) | 109.7 (3) |
C16—C20—C19 | 109.6 (3) | 109.0 (3) | 110.0 (3) |
C14—C21—C19 | 109.5 (3) | 109.1 (3) | 109.9 (3) |
| | | |
O10—C01—C02—C04 | 0.8 (3) | -9.8 (3) | 9.0 (3) |
O09—C01—C02—C06 | 0.6 (4) | -15.6 (4) | 15.1 (4) |
O09—C01—C02—C04 | -46.8 (3) | -180.00 (6) | 179.6 (3) |
O10—C01—C02—C06 | -8.8 (3) | -179.9 (3) | 179.4 (3) |
Experimental details
Crystal data |
Chemical formula | C17H22FNO2 |
Mr | 291.4 |
Crystal system, space group | Monoclinic, P21/n(α0γ)00† |
Temperature (K) | 97 |
Wave vectors | q = 0.423700a* + 0.428400c* |
a, b, c (Å) | 10.8498 (1), 6.5247 (1), 21.3826 (3) |
β (°) | 98.246 (1) |
V (Å3) | 1498.06 (3) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.75 |
Crystal size (mm) | 0.80 × 0.02 × 0.02 |
|
Data collection |
Diffractometer | Oxford Diffraction CCD diffractometer |
Absorption correction | Empirical |
No. of measured, independent and observed [I > 3σ(I)] reflections | 29463, 11225, 6001 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.591 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.071, 1.76 |
No. of reflections | 11225 |
No. of parameters | 991 |
No. of restraints | 6 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.26, −0.27 |
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