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At low temperatures the organic salt adamantan-1-ammonium 4-fluorobenzoate, C10H18N+·C7H4FO2, 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 P21/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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520614007707/dk5025sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614007707/dk5025Isup2.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520614007707/dk5025sup3.pdf
Extra figures and tables

B-IncStrDB reference: 9672EtfncG

CCDC reference: 995840

Computing details top

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
(I) top
Crystal data top
C17H22FNO2V = 1498.06 (3) Å3
Mr = 291.4Z = 4
Monoclinic, P21/n(α0γ)00†F(000) = 624
q = 0.423700a* + 0.428400c*Dx = 1.291 Mg m3
a = 10.8498 (1) ÅCu Kα radiation, λ = 1.5418 Å
b = 6.5247 (1) ŵ = 0.75 mm1
c = 21.3826 (3) ÅT = 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 tubeRint = 0.033
Graphite monochromatorθmax = 65.7°, θmin = 3.5°
Absorption correction: empirical
?
h = 1212
Tmin = ?, Tmax = ?k = 73
29463 measured reflectionsl = 2525
11225 independent reflections
Refinement top
Refinement on F307 constraints
R[F2 > 2σ(F2)] = 0.051H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.071Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.000121F2)
S = 1.76(Δ/σ)max = 0.003
11225 reflectionsΔρmax = 0.26 e Å3
991 parametersΔρmin = 0.27 e Å3
6 restraints
Crystal data top
C17H22FNO2β = 98.246 (1)°
Mr = 291.4V = 1498.06 (3) Å3
Monoclinic, P21/n(α0γ)00†Z = 4
q = 0.423700a* + 0.428400c*Cu Kα radiation
a = 10.8498 (1) ŵ = 0.75 mm1
b = 6.5247 (1) ÅT = 97 K
c = 21.3826 (3) Å0.80 × 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)] = 0.0516 restraints
wR(F2) = 0.071H atoms treated by a mixture of independent and constrained refinement
S = 1.76Δρmax = 0.26 e Å3
11225 reflectionsΔρmin = 0.27 e Å3
991 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C010.06259 (9)0.38058 (15)0.15316 (6)0.0306 (3)
C020.02518 (9)0.29051 (15)0.09876 (5)0.0310 (3)
C030.09126 (11)0.41989 (16)0.05531 (6)0.0390 (4)
C040.17229 (11)0.34689 (17)0.00443 (6)0.0428 (4)
C050.18623 (11)0.14257 (17)0.00211 (6)0.0420 (4)
C060.12363 (16)0.00717 (19)0.03990 (8)0.0523 (5)
C070.04147 (13)0.08249 (17)0.09034 (6)0.0423 (4)
F080.26562 (8)0.06883 (11)0.05162 (4)0.0608 (3)
O090.12359 (7)0.26017 (11)0.19206 (4)0.0375 (3)
O100.06978 (8)0.57222 (12)0.15579 (4)0.0418 (3)
N110.14166 (8)0.13244 (13)0.24462 (4)0.0317 (3)
C120.05548 (9)0.13331 (13)0.29297 (5)0.0285 (3)
C130.09251 (10)0.03906 (13)0.34078 (5)0.0331 (3)
C140.00475 (11)0.03839 (14)0.39012 (6)0.0372 (4)
C150.01334 (10)0.16851 (14)0.42492 (6)0.0355 (3)
C160.02291 (9)0.34135 (13)0.37675 (5)0.0322 (3)
C170.06498 (9)0.34024 (13)0.32721 (5)0.0307 (3)
C180.07819 (9)0.09895 (13)0.26048 (5)0.0307 (3)
C190.16604 (9)0.10039 (14)0.30998 (6)0.0349 (3)
C200.15685 (10)0.30724 (14)0.34471 (6)0.0351 (3)
C210.12916 (11)0.07209 (14)0.35808 (6)0.0385 (4)
H030.0804750.5638040.0606770.0468*
H040.2174710.437860.0254330.0514*
H060.1365340.1360560.0344280.0627*
H070.0045020.0099520.1195860.0507*
H11a0.2175 (10)0.1501 (13)0.2626 (6)0.0476*
H11b0.1354 (10)0.0108 (15)0.2242 (5)0.0476*
H11c0.1202 (11)0.2339 (14)0.2166 (5)0.0476*
H13a0.086970.1684850.3192350.0398*
H13b0.1762660.0173570.3610680.0398*
H140.0280770.1466460.4198280.0446*
H15a0.0426760.1686480.4557980.0425*
H15b0.0970660.189640.4453410.0425*
H160.0169010.4712430.3980350.0387*
H17a0.1488610.3608790.3474810.0368*
H17b0.0421310.447940.2972450.0368*
H18a0.1010380.2064730.230450.0369*
H18b0.0836040.0309170.2391880.0369*
H190.2498230.0797570.2895580.0419*
H20a0.1802330.4153630.3149820.0421*
H20b0.2118360.3071310.376070.0421*
H21a0.1842350.071080.3893970.0462*
H21b0.1350380.2017580.3366760.0462*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C010.0232 (5)0.0433 (6)0.0247 (7)0.0005 (3)0.0019 (4)0.0020 (4)
C020.0230 (5)0.0467 (6)0.0234 (7)0.0027 (4)0.0032 (4)0.0014 (4)
C030.0354 (6)0.0436 (6)0.0348 (8)0.0074 (4)0.0057 (5)0.0057 (4)
C040.0354 (6)0.0522 (6)0.0364 (8)0.0020 (4)0.0101 (5)0.0082 (5)
C050.0367 (6)0.0543 (6)0.0314 (8)0.0051 (5)0.0080 (5)0.0120 (5)
C060.0618 (11)0.0448 (6)0.0443 (9)0.0158 (7)0.0125 (8)0.0165 (6)
C070.0453 (8)0.0439 (6)0.0338 (8)0.0171 (6)0.0077 (6)0.0076 (5)
F080.0613 (5)0.0646 (4)0.0465 (5)0.0057 (3)0.0260 (4)0.0175 (3)
O090.0274 (4)0.0536 (4)0.0284 (5)0.0009 (3)0.0064 (3)0.0047 (3)
O100.0420 (4)0.0496 (5)0.0302 (5)0.0002 (3)0.0074 (3)0.0048 (3)
N110.0233 (4)0.0460 (5)0.0238 (5)0.0006 (3)0.0038 (3)0.0024 (4)
C120.0251 (5)0.0360 (5)0.0229 (6)0.0030 (3)0.0012 (4)0.0020 (4)
C130.0328 (5)0.0378 (5)0.0274 (7)0.0083 (4)0.0009 (4)0.0020 (4)
C140.0441 (6)0.0351 (5)0.0318 (7)0.0075 (4)0.0039 (5)0.0087 (4)
C150.0372 (6)0.0447 (5)0.0241 (6)0.0063 (4)0.0029 (4)0.0021 (4)
C160.0344 (5)0.0337 (4)0.0273 (6)0.0039 (3)0.0002 (4)0.0014 (4)
C170.0275 (5)0.0348 (5)0.0273 (6)0.0003 (3)0.0040 (4)0.0023 (4)
C180.0252 (5)0.0369 (5)0.0280 (6)0.0010 (3)0.0031 (4)0.0003 (4)
C190.0243 (5)0.0434 (5)0.0357 (7)0.0003 (3)0.0002 (4)0.0016 (4)
C200.0303 (5)0.0381 (5)0.0363 (7)0.0064 (3)0.0023 (4)0.0011 (4)
C210.0412 (6)0.0353 (5)0.0408 (8)0.0026 (4)0.0119 (5)0.0013 (4)
Geometric parameters (Å, º) top
AverageMinimumMaximum
C01—C021.513 (5)1.498 (5)1.528 (5)
C01—O091.261 (4)1.239 (5)1.280 (4)
C01—O101.254 (4)1.236 (4)1.268 (4)
C02—C031.386 (5)1.365 (5)1.405 (5)
C02—C071.388 (5)1.368 (5)1.406 (5)
C03—C041.382 (6)1.371 (6)1.393 (6)
C04—C051.360 (5)1.344 (5)1.380 (5)
C05—C061.378 (6)1.356 (6)1.402 (6)
C05—F081.355 (5)1.346 (5)1.365 (5)
C06—C071.388 (6)1.380 (7)1.397 (6)
N11—C121.491 (5)1.479 (5)1.499 (5)
C12—C131.535 (4)1.528 (4)1.540 (4)
C12—C171.533 (4)1.520 (4)1.548 (4)
C12—C181.533 (4)1.526 (4)1.542 (4)
C13—C141.520 (5)1.513 (5)1.527 (5)
C14—C151.538 (4)1.527 (4)1.551 (4)
C14—C211.531 (5)1.524 (5)1.535 (5)
C15—C161.541 (5)1.535 (5)1.547 (4)
C16—C171.525 (5)1.518 (5)1.531 (5)
C16—C201.532 (5)1.521 (5)1.544 (5)
C18—C191.524 (5)1.515 (5)1.532 (5)
C19—C201.537 (4)1.516 (4)1.558 (4)
C19—C211.539 (5)1.530 (5)1.548 (5)
C02—C01—O09118.6 (3)117.0 (3)119.7 (3)
C02—C01—O10116.8 (3)116.0 (3)117.7 (3)
O09—C01—O10124.7 (3)123.9 (3)125.5 (4)
C01—C02—C03119.1 (3)118.1 (3)119.7 (3)
C01—C02—C07122.4 (3)121.7 (3)123.1 (3)
C03—C02—C07118.5 (3)117.8 (4)119.4 (3)
C02—C03—C04121.6 (3)120.9 (3)122.3 (3)
C03—C04—C05118.1 (4)117.4 (4)118.9 (4)
C04—C05—C06122.6 (4)121.4 (4)124.1 (4)
C04—C05—F08118.9 (4)118.1 (4)119.4 (4)
C06—C05—F08118.5 (3)117.6 (4)119.4 (3)
C05—C06—C07118.5 (4)117.5 (4)119.7 (3)
C02—C07—C06120.5 (4)120.1 (4)120.8 (4)
N11—C12—C13109.2 (3)108.8 (3)109.5 (3)
N11—C12—C17109.2 (3)108.9 (3)109.5 (3)
N11—C12—C18109.4 (3)108.5 (3)110.2 (3)
C13—C12—C17109.6 (3)109.1 (3)110.2 (3)
C13—C12—C18109.6 (2)109.1 (3)110.0 (2)
C17—C12—C18109.9 (2)109.4 (2)110.4 (3)
C12—C13—C14109.3 (3)109.1 (3)109.6 (3)
C13—C14—C15109.8 (3)109.6 (3)110.0 (3)
C13—C14—C21109.8 (3)109.4 (3)110.1 (3)
C15—C14—C21109.3 (3)108.6 (3)109.7 (3)
C14—C15—C16109.1 (3)108.4 (3)109.9 (3)
C15—C16—C17109.6 (3)109.4 (3)109.9 (3)
C15—C16—C20109.1 (3)108.8 (3)109.3 (3)
C17—C16—C20109.7 (3)109.5 (3)110.0 (3)
C12—C17—C16109.3 (3)109.0 (3)109.7 (3)
C12—C18—C19109.3 (3)108.8 (3)109.7 (3)
C18—C19—C20109.7 (3)109.5 (3)110.1 (3)
C18—C19—C21109.4 (3)109.0 (3)109.6 (3)
C20—C19—C21109.1 (3)108.4 (3)109.7 (3)
C16—C20—C19109.6 (3)109.0 (3)110.0 (3)
C14—C21—C19109.5 (3)109.1 (3)109.9 (3)
O10—C01—C02—C040.8 (3)-9.8 (3)9.0 (3)
O09—C01—C02—C060.6 (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 formulaC17H22FNO2
Mr291.4
Crystal system, space groupMonoclinic, P21/n(α0γ)00†
Temperature (K)97
Wave vectorsq = 0.423700a* + 0.428400c*
a, b, c (Å)10.8498 (1), 6.5247 (1), 21.3826 (3)
β (°) 98.246 (1)
V3)1498.06 (3)
Z4
Radiation typeCu Kα
µ (mm1)0.75
Crystal size (mm)0.80 × 0.02 × 0.02
Data collection
DiffractometerOxford Diffraction CCD
diffractometer
Absorption correctionEmpirical
No. of measured, independent and
observed [I > 3σ(I)] reflections
29463, 11225, 6001
Rint0.033
(sin θ/λ)max1)0.591
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.071, 1.76
No. of reflections11225
No. of parameters991
No. of restraints6
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.26, 0.27

† 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.

 

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