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Four datasets on [2,2]-paracyclophane were collected in-house and at the Advanced Photon Source at two different temperatures for charge density investigation. Global data quality indicators such as high resolution, high I/σ(I) values, low merging R values and high multiplicity were matched for all four datasets. The structural parameters did not show significant differences, but the synchrotron data depicted deficiencies in the topological analysis. In retrospect these deficiencies could be assigned to the low quality of the innermost data, which could have been identified by e.g. merging R values for only these reflections. In the multipole refinement these deficiencies could be monitored using DRK-plot and residual density analysis. In this particular example the differences in the topological parameters were relatively small but significant.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520614026080/bm5068sup1.cif
Contains datablocks para, aps1, mo2, aps2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614026080/bm5068parasup2.hkl
Contains datablock para

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614026080/bm5068aps1sup3.hkl
Contains datablock aps1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614026080/bm5068mo2sup4.hkl
Contains datablock mo2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614026080/bm5068aps2sup5.hkl
Contains datablock aps2

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520614026080/bm5068sup6.pdf
Supporting tables and figures

CCDC references: 1036458; 1036459; 1036460; 1036461

Computing details top

For all compounds, data collection: ApexII; cell refinement: SAINT V8.30C; data reduction: SAINT V8.30C. Program(s) used to solve structure: SHELXS in SHELXTL Version 2008/4 for aps1, mo2, aps2. For all compounds, program(s) used to refine structure: Volkov et al., (2006); molecular graphics: Volkov et al., (2006); software used to prepare material for publication: Volkov et al., (2006).

(para) [2,2]-Paracyclophane top
Crystal data top
C16H16F(000) = 224
Mr = 208.29Dx = 1.278 Mg m3
Tetragonal, P4n2Mo Kα radiation, λ = 0.71073 Å
a = 7.6726 (1) ŵ = 0.07 mm1
c = 9.1910 (2) ÅT = 15 K
V = 541.06 (2) Å3Block, colorless
Z = 20.23 × 0.20 × 0.16 mm
Data collection top
APEX II CCD
diffractometer
4297 reflections with I > 2σ(I)
Radiation source: Mo TXSRint = 0.021
ω scansθmax = 62.7°, θmin = 3.5°
Absorption correction: multi-scan
SADABS-2014/2,Sheldrick
h = 1915
Tmin = 0.975, Tmax = 1.000k = 1918
32293 measured reflectionsl = 2222
4407 independent reflections
Refinement top
Refinement on F24389 reflections
Least-squares matrix: full118 parameters
R[F2 > 2σ(F2)] = 0.0130 restraints
wR(F2) = 0.032 w2 = q/[s2(Fo2) + (0.01 P)2 + 0.01 P + 0.00 + 0.00 sin(th)]
where P = (0.3333 Fo2 + 0.6667 Fc2) q = 1.0
S = 2.13(Δ/σ)max < 0.001
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C(1)0.123242 (15)0.633427 (14)0.903323 (10)0.006
C(2)0.250923 (15)0.535568 (15)0.831235 (12)0.007
C(3)0.061568 (16)0.583716 (15)1.053601 (12)0.008
C(4)0.255107 (15)0.529904 (15)0.679554 (12)0.007
H(2)0.329760.4461450.8928930.008193 (18)
H(4)0.3392030.4404890.6229370.008169 (18)
H(31)0.0156270.6895881.0980050.01022 (2)
H(32)0.1687010.5551011.1268590.01022 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C(1)0.00604 (3)0.00599 (3)0.00614 (2)0.00027 (2)0.00004 (2)0.00009 (2)
C(2)0.00600 (3)0.00707 (3)0.00738 (3)0.00102 (2)0.00052 (2)0.00029 (2)
C(3)0.00914 (4)0.00849 (3)0.00595 (3)0.00218 (3)0.00008 (2)0.00063 (2)
C(4)0.00601 (3)0.00702 (3)0.00742 (3)0.00106 (2)0.00039 (2)0.00042 (2)
Geometric parameters (Å, º) top
C(1)—C(2)1.4009 (2)C(2)—H(2)1.0760 (1)
C(1)—C(3)1.5090 (2)C(3)—H(31)1.0850 (1)
C(1)—C(4)i1.4017 (2)C(3)—H(32)1.0850 (1)
C(2)—C(4)1.3952 (1)C(4)—H(4)1.0760 (1)
C(2)—C(1)—C(3)121.113 (10)C(1)—C(3)—H(31)109.040 (10)
C(2)—C(1)—C(4)i117.210 (9)C(1)—C(3)—H(32)112.432 (10)
C(3)—C(1)—C(4)i120.368 (10)H(31)—C(3)—H(32)109.368 (9)
C(1)—C(2)—C(4)120.358 (10)C(1)i—C(4)—C(2)120.783 (11)
C(1)—C(2)—H(2)119.064 (10)C(1)i—C(4)—H(4)117.539 (10)
C(4)—C(2)—H(2)119.570 (11)C(2)—C(4)—H(4)121.125 (11)
Symmetry code: (i) y1/2, x+1/2, z+3/2.
(aps1) [2,2]-Paracyclophane top
Crystal data top
C16H16F(000) = 224
Mr = 208.29Dx = 1.282 Mg m3
Tetragonal, P4n2Synchrotron radiation, λ = 0.3936 Å
a = 7.6619 (1) ŵ = 0.07 mm1
c = 9.1830 (2) ÅT = 15 K
V = 539.09 (2) Å3Block, colorless
Z = 20.12 × 0.11 × 0.10 mm
Data collection top
ApexII CCD
diffractometer
4303 reflections with I > 2σ(I)
Radiation source: 15-ID-B,APSRint = 0.056
phi scansθmax = 29.4°, θmin = 1.9°
Absorption correction: multi-scan
SADABS-2014/2,Sheldrick
h = 1419
Tmin = 0.936, Tmax = 1.000k = 1418
41593 measured reflectionsl = 2222
4407 independent reflections
Refinement top
Refinement on F24388 reflections
Least-squares matrix: full118 parameters
R[F2 > 2σ(F2)] = 0.0170 restraints
wR(F2) = 0.035 w2 = q/[s2(Fo2) + (0.01 P)2 + 0.00 P + 0.00 + 0.00 sin(th)]
where P = (0.3333 Fo2 + 0.6667 Fc2) q = 1.0
S = 1.36(Δ/σ)max < 0.001
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C(1)0.123238 (14)0.633459 (13)0.903296 (9)0.006
C(2)0.250865 (13)0.535576 (14)0.831254 (11)0.007
C(3)0.061543 (15)0.583712 (15)1.053621 (10)0.008
C(4)0.255142 (13)0.529920 (14)0.679587 (11)0.007
H(2)0.3269730.4422520.8915370.008122 (18)
H(4)0.3423410.4404290.6260980.008119 (17)
H(31)0.0154460.6862621.1037490.01013 (2)
H(32)0.1722740.5547791.1232020.01013 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C(1)0.00596 (3)0.00588 (3)0.00599 (2)0.00034 (2)0.000035 (18)0.000110 (18)
C(2)0.00590 (3)0.00688 (3)0.00717 (2)0.00098 (2)0.000495 (18)0.000362 (19)
C(3)0.00896 (3)0.00827 (3)0.00570 (2)0.00212 (3)0.00007 (2)0.00060 (2)
C(4)0.00585 (3)0.00689 (3)0.00727 (2)0.00102 (2)0.000398 (19)0.00045 (2)
Geometric parameters (Å, º) top
C(1)—C(2)1.3987 (2)C(2)—H(2)1.0760 (1)
C(1)—C(3)1.5081 (1)C(3)—H(31)1.0850 (1)
C(1)—C(4)i1.3999 (2)C(3)—H(32)1.0850 (1)
C(2)—C(4)1.3938 (1)C(4)—H(4)1.0760 (1)
C(2)—C(1)—C(3)121.102 (9)C(1)—C(3)—H(31)112.070 (9)
C(2)—C(1)—C(4)i117.195 (8)C(1)—C(3)—H(32)110.219 (9)
C(3)—C(1)—C(4)i120.391 (9)H(31)—C(3)—H(32)108.858 (8)
C(1)—C(2)—C(4)120.380 (9)C(1)i—C(4)—C(2)120.780 (9)
C(1)—C(2)—H(2)119.463 (9)C(1)i—C(4)—H(4)119.393 (9)
C(4)—C(2)—H(2)118.730 (10)C(2)—C(4)—H(4)119.377 (10)
Symmetry code: (i) y1/2, x+1/2, z+3/2.
(mo2) [2,2]-Paracyclophane top
Crystal data top
C16H16F(000) = 224
Mr = 208.29Dx = 1.278 Mg m3
Tetragonal, P4n2Mo Kα radiation, λ = 0.71073 Å
a = 7.6761 (1) ŵ = 0.07 mm1
c = 9.1966 (2) ÅT = 35 K
V = 541.89 (2) Å3Block, colorless
Z = 20.23 × 0.20 × 0.16 mm
Data collection top
APEX II CCD
diffractometer
3763 reflections with I > 2σ(I)
Radiation source: Mo TXSRint = 0.017
ω scansθmax = 57.9°, θmin = 3.5°
Absorption correction: multi-scan
SADABS-2014/2,Sheldrick
h = 1817
Tmin = 0.975, Tmax = 1.000k = 1817
34569 measured reflectionsl = 2119
3834 independent reflections
Refinement top
Refinement on F23822 reflections
Least-squares matrix: full118 parameters
R[F2 > 2σ(F2)] = 0.0120 restraints
wR(F2) = 0.027 w2 = q/[s2(Fo2) + (0.01 P)2 + 0.01 P + 0.00 + 0.00 sin(th)]
where P = (0.3333 Fo2 + 0.6667 Fc2) q = 1.0
S = 2.78(Δ/σ)max < 0.001
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C(1)0.123525 (14)0.633022 (14)0.903242 (11)0.008
C(2)0.250907 (14)0.535369 (15)0.830826 (12)0.009
C(3)0.062172 (16)0.583105 (16)1.053466 (12)0.011
C(4)0.254854 (14)0.530090 (14)0.679214 (12)0.009
H(2)0.3288750.4445530.8917210.01056 (2)
H(4)0.3396710.4412570.6228270.01054 (2)
H(31)0.0151760.6880541.0990470.01315 (3)
H(32)0.168780.5528751.1267080.01315 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C(1)0.00781 (3)0.00781 (3)0.00852 (3)0.00069 (2)0.00012 (2)0.00024 (2)
C(2)0.00743 (3)0.00872 (3)0.01042 (3)0.00106 (2)0.00084 (2)0.00044 (2)
C(3)0.01232 (4)0.01174 (4)0.00823 (3)0.00343 (3)0.00007 (3)0.00093 (3)
C(4)0.00732 (3)0.00875 (3)0.01054 (3)0.00112 (2)0.00071 (2)0.00068 (2)
Geometric parameters (Å, º) top
C(1)—C(2)1.4005 (2)C(2)—H(2)1.0760 (1)
C(1)—C(3)1.5091 (2)C(3)—H(31)1.0850 (1)
C(1)—C(4)i1.4014 (2)C(3)—H(32)1.0850 (1)
C(2)—C(4)1.3952 (1)C(4)—H(4)1.0760 (1)
C(2)—C(1)—C(3)121.153 (11)C(1)—C(3)—H(31)109.631 (10)
C(2)—C(1)—C(4)i117.204 (9)C(1)—C(3)—H(32)112.785 (10)
C(3)—C(1)—C(4)i120.338 (11)H(31)—C(3)—H(32)109.370 (10)
C(1)—C(2)—C(4)120.392 (10)C(1)i—C(4)—C(2)120.756 (10)
C(1)—C(2)—H(2)119.182 (10)C(1)i—C(4)—H(4)117.861 (10)
C(4)—C(2)—H(2)119.290 (11)C(2)—C(4)—H(4)120.875 (11)
Symmetry code: (i) y1/2, x+1/2, z+3/2.
(aps2) [2,2]-Paracyclophane top
Crystal data top
C16H16F(000) = 224
Mr = 208.29Dx = 1.282 Mg m3
Tetragonal, P4n2Synchrotron radiation, λ = 0.3936 Å
a = 7.6648 (1) ŵ = 0.07 mm1
c = 9.1858 (2) ÅT = 35 K
V = 539.66 (2) Å3Block, colorless
Z = 20.12 × 0.11 × 0.10 mm
Data collection top
ApexII CCD
diffractometer
3418 reflections with I > 2σ(I)
Radiation source: 15-ID-B, APSRint = 0.043
phi scansθmax = 27.2°, θmin = 1.9°
Absorption correction: multi-scan
SADABS-2014/2,Sheldrick
h = 1713
Tmin = 0.924, Tmax = 1.000k = 1117
29629 measured reflectionsl = 2115
3544 independent reflections
Refinement top
Refinement on F23525 reflections
Least-squares matrix: full118 parameters
R[F2 > 2σ(F2)] = 0.0160 restraints
wR(F2) = 0.035 w2 = q/[s2(Fo2) + (0.02 P)2 + 0.00 P + 0.00 + 0.00 sin(th)]
where P = (0.3333 Fo2 + 0.6667 Fc2) q = 1.0
S = 1.80(Δ/σ)max < 0.001
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C(1)0.123500 (16)0.633105 (16)0.903241 (11)0.008
C(2)0.250905 (16)0.535411 (17)0.830887 (14)0.009
C(3)0.062107 (19)0.583167 (18)1.053483 (12)0.011
C(4)0.254879 (16)0.530092 (16)0.679265 (14)0.009
H(2)0.3228210.439910.8922880.01074 (2)
H(4)0.341410.4434340.6220.01072 (2)
H(31)0.1689690.5502531.1259170.01336 (3)
H(32)0.0158250.6869841.1005870.01336 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C(1)0.00784 (4)0.00787 (4)0.00858 (3)0.00067 (3)0.00004 (3)0.00025 (3)
C(2)0.00751 (4)0.00880 (4)0.01033 (4)0.00105 (3)0.00085 (3)0.00045 (3)
C(3)0.01230 (4)0.01167 (4)0.00828 (3)0.00328 (3)0.00008 (3)0.00095 (3)
C(4)0.00740 (4)0.00876 (4)0.01055 (4)0.00107 (3)0.00071 (3)0.00065 (3)
Geometric parameters (Å, º) top
C(1)—C(2)1.3986 (2)C(2)—H(2)1.0760 (1)
C(1)—C(3)1.5075 (2)C(3)—H(31)1.0850 (1)
C(1)—C(4)i1.3993 (2)C(3)—H(32)1.0850 (2)
C(2)—C(4)1.3937 (2)C(4)—H(4)1.0760 (1)
C(2)—C(1)—C(3)121.135 (12)C(1)—C(3)—H(31)112.631 (11)
C(2)—C(1)—C(4)i117.192 (9)C(1)—C(3)—H(32)110.531 (12)
C(3)—C(1)—C(4)i120.363 (12)H(31)—C(3)—H(32)109.973 (10)
C(1)—C(2)—C(4)120.386 (11)C(1)i—C(4)—C(2)120.777 (11)
C(1)—C(2)—H(2)118.218 (11)C(1)i—C(4)—H(4)117.529 (11)
C(4)—C(2)—H(2)119.520 (12)C(2)—C(4)—H(4)121.337 (12)
Symmetry code: (i) y1/2, x+1/2, z+3/2.
 

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