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Crystallization of 5,5'-diphenyl-2,2'-(p-phenylene)di-1,3-oxazole (POPOP), C24H16N2O2, from chloroform or 1,4-dioxane yielded crystals in pure and solvated forms, respectively. The solvated crystals of POPOP were found to contain 1,4-dioxane in a strict 1:2 compound-solvent stoichiometry, C24H16N2O2·C4H8O2, thus being a defined solvent-inclusion compound. The crystal system is monoclinic in both cases and the asymmetric unit of the cell contains only half of the molecule (plus one dioxane molecule in the case of the solvated structure), owing to the centrosymmetry of the di-1,3-oxazole molecule.
Supporting information
CCDC references: 786818; 786819
For both compounds, data collection: SMART (Bruker, 2003); cell refinement: SMART (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
(I) 5,5'-diphenyl-2,2'-(
p-phenylene)di-1,3-oxazole
top
Crystal data top
C24H16N2O2 | F(000) = 380 |
Mr = 364.39 | Dx = 1.315 Mg m−3 |
Monoclinic, P21/c | Melting point = 517–519 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 9.1393 (14) Å | Cell parameters from 2741 reflections |
b = 5.2461 (8) Å | θ = 2.2–29.2° |
c = 19.204 (3) Å | µ = 0.09 mm−1 |
β = 91.807 (11)° | T = 153 K |
V = 920.3 (3) Å3 | Plate, colourless |
Z = 2 | 0.27 × 0.14 × 0.11 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2107 independent reflections |
Radiation source: fine-focus sealed tube | 1644 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
φ and ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −11→11 |
Tmin = 0.978, Tmax = 0.991 | k = −6→6 |
16533 measured reflections | l = −24→24 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.094 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0404P)2 + 0.2332P] where P = (Fo2 + 2Fc2)/3 |
2107 reflections | (Δ/σ)max < 0.001 |
127 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
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) |
C1 | 0.38668 (13) | 0.8295 (2) | −0.01505 (6) | 0.0247 (3) | |
H1 | 0.3091 | 0.7135 | −0.0253 | 0.030* | |
C2 | 0.57922 (13) | 0.9840 (2) | 0.06280 (6) | 0.0248 (3) | |
H2 | 0.6331 | 0.9733 | 0.1058 | 0.030* | |
C3 | 0.46596 (13) | 0.8113 (2) | 0.04816 (6) | 0.0222 (3) | |
C4 | 0.43224 (13) | 0.6177 (2) | 0.09976 (6) | 0.0224 (3) | |
C5 | 0.42273 (14) | 0.3743 (2) | 0.18784 (6) | 0.0261 (3) | |
H5 | 0.4451 | 0.2979 | 0.2318 | 0.031* | |
C6 | 0.31054 (13) | 0.3051 (2) | 0.14422 (6) | 0.0234 (3) | |
C7 | 0.19573 (13) | 0.1136 (2) | 0.14648 (6) | 0.0237 (3) | |
C8 | 0.08296 (15) | 0.1035 (3) | 0.09601 (7) | 0.0306 (3) | |
H8 | 0.0797 | 0.2243 | 0.0591 | 0.037* | |
C9 | −0.02462 (15) | −0.0822 (3) | 0.09940 (7) | 0.0362 (3) | |
H9 | −0.1007 | −0.0888 | 0.0646 | 0.043* | |
C10 | −0.02188 (15) | −0.2579 (3) | 0.15314 (8) | 0.0352 (3) | |
H10 | −0.0961 | −0.3841 | 0.1554 | 0.042* | |
C11 | 0.08988 (15) | −0.2491 (2) | 0.20384 (7) | 0.0318 (3) | |
H11 | 0.0920 | −0.3694 | 0.2408 | 0.038* | |
C12 | 0.19801 (14) | −0.0655 (2) | 0.20057 (7) | 0.0267 (3) | |
H12 | 0.2744 | −0.0609 | 0.2353 | 0.032* | |
Cg1 | 0.0867 | −0.0729 | 0.1499 | 0.010* | 0.00 |
Cg2 | 0.3962 | 0.4663 | 0.1355 | 0.010* | 0.00 |
N1 | 0.50023 (12) | 0.57309 (19) | 0.15899 (5) | 0.0258 (2) | |
O1 | 0.31544 (9) | 0.46141 (16) | 0.08657 (4) | 0.0234 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0252 (6) | 0.0238 (6) | 0.0250 (6) | −0.0009 (5) | 0.0003 (5) | −0.0011 (5) |
C2 | 0.0262 (6) | 0.0262 (6) | 0.0219 (6) | 0.0025 (5) | −0.0013 (5) | 0.0001 (5) |
C3 | 0.0246 (6) | 0.0217 (6) | 0.0206 (6) | 0.0039 (5) | 0.0036 (5) | −0.0007 (5) |
C4 | 0.0242 (6) | 0.0212 (6) | 0.0219 (6) | 0.0009 (5) | 0.0015 (5) | −0.0027 (5) |
C5 | 0.0327 (7) | 0.0228 (6) | 0.0227 (6) | 0.0009 (5) | 0.0008 (5) | 0.0026 (5) |
C6 | 0.0286 (6) | 0.0214 (6) | 0.0204 (6) | 0.0045 (5) | 0.0041 (5) | 0.0015 (5) |
C7 | 0.0252 (6) | 0.0225 (6) | 0.0236 (6) | 0.0032 (5) | 0.0047 (5) | −0.0020 (5) |
C8 | 0.0333 (7) | 0.0320 (7) | 0.0265 (7) | −0.0010 (6) | 0.0007 (5) | 0.0027 (5) |
C9 | 0.0315 (7) | 0.0419 (8) | 0.0351 (8) | −0.0044 (6) | −0.0002 (6) | −0.0071 (6) |
C10 | 0.0333 (7) | 0.0305 (7) | 0.0424 (8) | −0.0064 (6) | 0.0104 (6) | −0.0065 (6) |
C11 | 0.0347 (7) | 0.0248 (7) | 0.0364 (7) | 0.0026 (5) | 0.0117 (6) | 0.0034 (5) |
C12 | 0.0271 (6) | 0.0256 (7) | 0.0275 (6) | 0.0042 (5) | 0.0047 (5) | 0.0012 (5) |
N1 | 0.0307 (6) | 0.0242 (5) | 0.0224 (5) | −0.0001 (4) | −0.0004 (4) | 0.0013 (4) |
O1 | 0.0260 (4) | 0.0235 (4) | 0.0209 (4) | −0.0011 (3) | 0.0007 (3) | 0.0024 (3) |
Geometric parameters (Å, º) top
C1—C2i | 1.3832 (17) | C6—C7 | 1.4544 (17) |
C1—C3 | 1.3970 (17) | C7—C8 | 1.3934 (18) |
C1—H1 | 0.9500 | C7—C12 | 1.4002 (17) |
C2—C1i | 1.3832 (17) | C8—C9 | 1.3871 (19) |
C2—C3 | 1.3977 (17) | C8—H8 | 0.9500 |
C2—H2 | 0.9500 | C9—C10 | 1.383 (2) |
C3—C4 | 1.4584 (17) | C9—H9 | 0.9500 |
C4—N1 | 1.3001 (15) | C10—C11 | 1.390 (2) |
C4—O1 | 1.3635 (14) | C10—H10 | 0.9500 |
C5—C6 | 1.3530 (17) | C11—C12 | 1.3825 (18) |
C5—N1 | 1.3859 (16) | C11—H11 | 0.9500 |
C5—H5 | 0.9500 | C12—H12 | 0.9500 |
C6—O1 | 1.3797 (14) | | |
| | | |
C2i—C1—C3 | 120.19 (11) | C8—C7—C6 | 121.60 (11) |
C2i—C1—H1 | 119.9 | C12—C7—C6 | 119.46 (11) |
C3—C1—H1 | 119.9 | C9—C8—C7 | 120.26 (12) |
C1i—C2—C3 | 120.41 (11) | C9—C8—H8 | 119.9 |
C1i—C2—H2 | 119.8 | C7—C8—H8 | 119.9 |
C3—C2—H2 | 119.8 | C10—C9—C8 | 120.45 (13) |
C1—C3—C2 | 119.40 (11) | C10—C9—H9 | 119.8 |
C1—C3—C4 | 121.54 (11) | C8—C9—H9 | 119.8 |
C2—C3—C4 | 119.06 (11) | C9—C10—C11 | 119.74 (13) |
N1—C4—O1 | 113.83 (10) | C9—C10—H10 | 120.1 |
N1—C4—C3 | 127.92 (11) | C11—C10—H10 | 120.1 |
O1—C4—C3 | 118.26 (10) | C12—C11—C10 | 120.14 (13) |
C6—C5—N1 | 109.96 (11) | C12—C11—H11 | 119.9 |
C6—C5—H5 | 125.0 | C10—C11—H11 | 119.9 |
N1—C5—H5 | 125.0 | C11—C12—C7 | 120.47 (12) |
C5—C6—O1 | 107.11 (11) | C11—C12—H12 | 119.8 |
C5—C6—C7 | 134.45 (11) | C7—C12—H12 | 119.8 |
O1—C6—C7 | 118.44 (10) | C4—N1—C5 | 104.43 (10) |
C8—C7—C12 | 118.94 (12) | C4—O1—C6 | 104.68 (9) |
| | | |
C2i—C1—C3—C2 | 0.4 (2) | C6—C7—C8—C9 | 179.70 (12) |
C2i—C1—C3—C4 | 179.67 (11) | C7—C8—C9—C10 | 0.5 (2) |
C1i—C2—C3—C1 | −0.4 (2) | C8—C9—C10—C11 | −0.3 (2) |
C1i—C2—C3—C4 | −179.69 (11) | C9—C10—C11—C12 | −0.1 (2) |
C1—C3—C4—N1 | 177.04 (12) | C10—C11—C12—C7 | 0.28 (19) |
C2—C3—C4—N1 | −3.70 (19) | C8—C7—C12—C11 | −0.10 (19) |
C1—C3—C4—O1 | −3.43 (17) | C6—C7—C12—C11 | 179.89 (11) |
C2—C3—C4—O1 | 175.83 (10) | O1—C4—N1—C5 | −0.56 (14) |
N1—C5—C6—O1 | −0.13 (14) | C3—C4—N1—C5 | 178.99 (12) |
N1—C5—C6—C7 | 179.87 (12) | C6—C5—N1—C4 | 0.41 (14) |
C5—C6—C7—C8 | 172.92 (14) | N1—C4—O1—C6 | 0.50 (13) |
O1—C6—C7—C8 | −7.09 (17) | C3—C4—O1—C6 | −179.10 (10) |
C5—C6—C7—C12 | −7.1 (2) | C5—C6—O1—C4 | −0.20 (12) |
O1—C6—C7—C12 | 172.92 (10) | C7—C6—O1—C4 | 179.80 (10) |
C12—C7—C8—C9 | −0.31 (19) | | |
Symmetry code: (i) −x+1, −y+2, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···N1ii | 0.95 | 2.44 | 3.3932 (16) | 176 |
C11—H11···Cg1iii | 0.95 | 2.90 | 3.6966 (14) | 142 |
Symmetry codes: (ii) −x+1, y−1/2, −z+1/2; (iii) −x, y−1/2, −z+1/2. |
(II) 5,5'-diphenyl-2,2'-(
p-phenylene)di-1,3-oxazole dioxane disolvate
top
Crystal data top
C24H16N2O2·2C4H8O2 | F(000) = 572 |
Mr = 540.60 | Dx = 1.354 Mg m−3 |
Monoclinic, P21/n | Melting point = 519–519 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 12.2424 (6) Å | Cell parameters from 4956 reflections |
b = 5.9115 (3) Å | θ = 3.4–32.3° |
c = 18.5046 (9) Å | µ = 0.09 mm−1 |
β = 97.977 (3)° | T = 153 K |
V = 1326.24 (11) Å3 | Needle, colourless |
Z = 2 | 0.44 × 0.11 × 0.09 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2324 independent reflections |
Radiation source: fine-focus sealed tube | 1857 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
φ and ω scans | θmax = 25.0°, θmin = 3.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −14→14 |
Tmin = 0.960, Tmax = 0.992 | k = −6→7 |
22800 measured reflections | l = −22→22 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.075 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0318P)2 + 0.4537P] where P = (Fo2 + 2Fc2)/3 |
2324 reflections | (Δ/σ)max < 0.001 |
181 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
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) |
C1 | 0.40678 (10) | 0.1364 (2) | −0.01121 (7) | 0.0227 (3) | |
H1 | 0.3429 | 0.2293 | −0.0189 | 0.027* | |
C2 | 0.58498 (10) | 0.0496 (2) | 0.05524 (7) | 0.0230 (3) | |
H2 | 0.6432 | 0.0834 | 0.0932 | 0.028* | |
C3 | 0.49169 (10) | 0.1887 (2) | 0.04453 (7) | 0.0211 (3) | |
C4 | 0.48480 (10) | 0.3818 (2) | 0.09274 (7) | 0.0211 (3) | |
C5 | 0.50790 (11) | 0.6286 (2) | 0.17666 (7) | 0.0257 (3) | |
H5 | 0.5396 | 0.7111 | 0.2184 | 0.031* | |
C6 | 0.41094 (10) | 0.6784 (2) | 0.13583 (7) | 0.0212 (3) | |
C7 | 0.32829 (10) | 0.8534 (2) | 0.13969 (7) | 0.0222 (3) | |
C8 | 0.22431 (11) | 0.8439 (2) | 0.09840 (7) | 0.0279 (3) | |
H8 | 0.2060 | 0.7220 | 0.0655 | 0.033* | |
C9 | 0.14739 (12) | 1.0118 (3) | 0.10520 (8) | 0.0328 (3) | |
H9 | 0.0766 | 1.0044 | 0.0768 | 0.039* | |
C10 | 0.17278 (12) | 1.1902 (2) | 0.15296 (8) | 0.0319 (3) | |
H10 | 0.1194 | 1.3037 | 0.1578 | 0.038* | |
C11 | 0.27666 (11) | 1.2024 (2) | 0.19378 (7) | 0.0288 (3) | |
H11 | 0.2948 | 1.3253 | 0.2263 | 0.035* | |
C12 | 0.35364 (11) | 1.0356 (2) | 0.18707 (7) | 0.0248 (3) | |
H12 | 0.4247 | 1.0450 | 0.2150 | 0.030* | |
N1 | 0.55444 (9) | 0.44003 (19) | 0.14900 (6) | 0.0255 (3) | |
O1 | 0.39440 (7) | 0.51870 (15) | 0.08077 (5) | 0.0215 (2) | |
C13 | 0.61584 (12) | 1.3224 (2) | 0.33040 (8) | 0.0315 (3) | |
H13A | 0.6465 | 1.4635 | 0.3126 | 0.038* | |
H13B | 0.5354 | 1.3212 | 0.3138 | 0.038* | |
C14 | 0.66792 (12) | 1.1228 (3) | 0.29878 (8) | 0.0344 (4) | |
H14A | 0.6516 | 1.1274 | 0.2449 | 0.041* | |
H14B | 0.7490 | 1.1296 | 0.3124 | 0.041* | |
C15 | 0.64950 (13) | 0.9120 (3) | 0.40270 (8) | 0.0355 (4) | |
H15A | 0.7302 | 0.9159 | 0.4181 | 0.043* | |
H15B | 0.6206 | 0.7701 | 0.4212 | 0.043* | |
C16 | 0.59690 (13) | 1.1111 (2) | 0.43462 (8) | 0.0338 (3) | |
H16A | 0.5158 | 1.1018 | 0.4216 | 0.041* | |
H16B | 0.6141 | 1.1065 | 0.4885 | 0.041* | |
O2 | 0.63519 (8) | 1.31862 (16) | 0.40845 (5) | 0.0326 (3) | |
O3 | 0.62697 (9) | 0.91601 (17) | 0.32503 (5) | 0.0379 (3) | |
CG1 | 0.2505 | 1.0229 | 0.1462 | 0.010* | 0.00 |
CG2 | 0.4705 | 0.5295 | 0.1270 | 0.010* | 0.00 |
CG3 | 0.5000 | 0.0000 | 0.0000 | 0.010* | 0.00 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0224 (6) | 0.0219 (7) | 0.0242 (7) | 0.0029 (5) | 0.0049 (5) | 0.0037 (5) |
C2 | 0.0227 (6) | 0.0236 (7) | 0.0226 (7) | −0.0011 (5) | 0.0027 (5) | 0.0017 (5) |
C3 | 0.0252 (6) | 0.0191 (7) | 0.0204 (6) | −0.0020 (5) | 0.0077 (5) | 0.0035 (5) |
C4 | 0.0210 (6) | 0.0194 (7) | 0.0236 (6) | 0.0000 (5) | 0.0058 (5) | 0.0044 (5) |
C5 | 0.0296 (7) | 0.0226 (7) | 0.0248 (7) | −0.0010 (6) | 0.0033 (6) | −0.0033 (6) |
C6 | 0.0271 (7) | 0.0177 (7) | 0.0197 (6) | −0.0026 (5) | 0.0063 (5) | −0.0008 (5) |
C7 | 0.0269 (7) | 0.0197 (7) | 0.0216 (6) | −0.0021 (5) | 0.0090 (5) | 0.0034 (5) |
C8 | 0.0312 (7) | 0.0254 (8) | 0.0271 (7) | 0.0001 (6) | 0.0043 (6) | −0.0025 (6) |
C9 | 0.0291 (7) | 0.0323 (8) | 0.0367 (8) | 0.0044 (6) | 0.0031 (6) | 0.0035 (7) |
C10 | 0.0347 (8) | 0.0250 (8) | 0.0383 (8) | 0.0077 (6) | 0.0134 (7) | 0.0045 (6) |
C11 | 0.0384 (8) | 0.0203 (7) | 0.0306 (8) | −0.0028 (6) | 0.0145 (6) | −0.0016 (6) |
C12 | 0.0269 (7) | 0.0238 (7) | 0.0249 (7) | −0.0040 (6) | 0.0084 (5) | 0.0007 (6) |
N1 | 0.0264 (6) | 0.0225 (6) | 0.0270 (6) | 0.0007 (5) | 0.0019 (5) | −0.0011 (5) |
O1 | 0.0236 (4) | 0.0192 (5) | 0.0223 (5) | 0.0019 (4) | 0.0047 (4) | −0.0013 (4) |
C13 | 0.0343 (8) | 0.0279 (8) | 0.0312 (8) | −0.0002 (6) | 0.0008 (6) | 0.0048 (6) |
C14 | 0.0354 (8) | 0.0359 (9) | 0.0315 (8) | 0.0026 (7) | 0.0041 (6) | 0.0031 (7) |
C15 | 0.0481 (9) | 0.0240 (8) | 0.0325 (8) | −0.0009 (7) | −0.0009 (7) | 0.0016 (6) |
C16 | 0.0416 (8) | 0.0283 (8) | 0.0308 (8) | −0.0019 (6) | 0.0030 (6) | 0.0027 (6) |
O2 | 0.0420 (6) | 0.0222 (5) | 0.0318 (5) | −0.0016 (4) | −0.0015 (4) | −0.0019 (4) |
O3 | 0.0533 (7) | 0.0266 (6) | 0.0321 (6) | −0.0018 (5) | −0.0006 (5) | −0.0045 (5) |
Geometric parameters (Å, º) top
C1—C2i | 1.3805 (19) | C10—H10 | 0.9500 |
C1—C3 | 1.3936 (18) | C11—C12 | 1.3813 (19) |
C1—H1 | 0.9500 | C11—H11 | 0.9500 |
C2—C1i | 1.3805 (19) | C12—H12 | 0.9500 |
C2—C3 | 1.3990 (18) | C13—O2 | 1.4310 (17) |
C2—H2 | 0.9500 | C13—C14 | 1.498 (2) |
C3—C4 | 1.4587 (18) | C13—H13A | 0.9900 |
C4—N1 | 1.2971 (16) | C13—H13B | 0.9900 |
C4—O1 | 1.3641 (15) | C14—O3 | 1.4314 (18) |
C5—C6 | 1.3482 (18) | C14—H14A | 0.9900 |
C5—N1 | 1.3820 (17) | C14—H14B | 0.9900 |
C5—H5 | 0.9500 | C15—O3 | 1.4257 (17) |
C6—O1 | 1.3830 (15) | C15—C16 | 1.501 (2) |
C6—C7 | 1.4557 (18) | C15—H15A | 0.9900 |
C7—C8 | 1.3919 (18) | C15—H15B | 0.9900 |
C7—C12 | 1.3963 (19) | C16—O2 | 1.4221 (17) |
C8—C9 | 1.386 (2) | C16—H16A | 0.9900 |
C8—H8 | 0.9500 | C16—H16B | 0.9900 |
C9—C10 | 1.383 (2) | CG3—C2i | 1.3849 (13) |
C9—H9 | 0.9500 | CG3—C1i | 1.3894 (13) |
C10—C11 | 1.388 (2) | | |
| | | |
C2i—C1—C3 | 120.34 (12) | C11—C12—C7 | 120.81 (13) |
C2i—C1—H1 | 119.8 | C11—C12—H12 | 119.6 |
C3—C1—H1 | 119.8 | C7—C12—H12 | 119.6 |
C1i—C2—C3 | 120.64 (12) | C4—N1—C5 | 104.62 (11) |
C1i—C2—H2 | 119.7 | C4—O1—C6 | 104.63 (10) |
C3—C2—H2 | 119.7 | O2—C13—C14 | 111.22 (11) |
C1—C3—C2 | 119.02 (12) | O2—C13—H13A | 109.4 |
C1—C3—C4 | 121.71 (11) | C14—C13—H13A | 109.4 |
C2—C3—C4 | 119.26 (11) | O2—C13—H13B | 109.4 |
N1—C4—O1 | 113.64 (11) | C14—C13—H13B | 109.4 |
N1—C4—C3 | 127.68 (12) | H13A—C13—H13B | 108.0 |
O1—C4—C3 | 118.65 (11) | O3—C14—C13 | 110.61 (11) |
C6—C5—N1 | 110.16 (11) | O3—C14—H14A | 109.5 |
C6—C5—H5 | 124.9 | C13—C14—H14A | 109.5 |
N1—C5—H5 | 124.9 | O3—C14—H14B | 109.5 |
C5—C6—O1 | 106.94 (11) | C13—C14—H14B | 109.5 |
C5—C6—C7 | 133.75 (12) | H14A—C14—H14B | 108.1 |
O1—C6—C7 | 119.30 (11) | O3—C15—C16 | 110.49 (12) |
C8—C7—C12 | 118.84 (12) | O3—C15—H15A | 109.6 |
C8—C7—C6 | 122.23 (12) | C16—C15—H15A | 109.6 |
C12—C7—C6 | 118.93 (12) | O3—C15—H15B | 109.6 |
C9—C8—C7 | 120.16 (13) | C16—C15—H15B | 109.6 |
C9—C8—H8 | 119.9 | H15A—C15—H15B | 108.1 |
C7—C8—H8 | 119.9 | O2—C16—C15 | 111.27 (12) |
C10—C9—C8 | 120.58 (13) | O2—C16—H16A | 109.4 |
C10—C9—H9 | 119.7 | C15—C16—H16A | 109.4 |
C8—C9—H9 | 119.7 | O2—C16—H16B | 109.4 |
C9—C10—C11 | 119.67 (13) | C15—C16—H16B | 109.4 |
C9—C10—H10 | 120.2 | H16A—C16—H16B | 108.0 |
C11—C10—H10 | 120.2 | C16—O2—C13 | 109.93 (10) |
C12—C11—C10 | 119.93 (13) | C15—O3—C14 | 109.17 (11) |
C12—C11—H11 | 120.0 | C2i—CG3—C1i | 120.32 (8) |
C10—C11—H11 | 120.0 | | |
| | | |
C2i—C1—C3—C2 | −0.2 (2) | C9—C10—C11—C12 | −0.7 (2) |
C2i—C1—C3—C4 | −179.00 (11) | C10—C11—C12—C7 | −0.2 (2) |
C1i—C2—C3—C1 | 0.2 (2) | C8—C7—C12—C11 | 0.87 (19) |
C1i—C2—C3—C4 | 179.03 (11) | C6—C7—C12—C11 | −178.36 (12) |
C1—C3—C4—N1 | 175.38 (13) | O1—C4—N1—C5 | −0.05 (14) |
C2—C3—C4—N1 | −3.4 (2) | C3—C4—N1—C5 | −178.03 (12) |
C1—C3—C4—O1 | −2.51 (18) | C6—C5—N1—C4 | −0.03 (14) |
C2—C3—C4—O1 | 178.69 (11) | N1—C4—O1—C6 | 0.10 (14) |
N1—C5—C6—O1 | 0.09 (14) | C3—C4—O1—C6 | 178.28 (10) |
N1—C5—C6—C7 | 179.60 (13) | C5—C6—O1—C4 | −0.11 (13) |
C5—C6—C7—C8 | −167.72 (14) | C7—C6—O1—C4 | −179.71 (11) |
O1—C6—C7—C8 | 11.75 (18) | O2—C13—C14—O3 | 57.68 (15) |
C5—C6—C7—C12 | 11.5 (2) | O3—C15—C16—O2 | −58.38 (16) |
O1—C6—C7—C12 | −169.05 (11) | C15—C16—O2—C13 | 56.11 (15) |
C12—C7—C8—C9 | −0.7 (2) | C14—C13—O2—C16 | −55.87 (15) |
C6—C7—C8—C9 | 178.46 (12) | C16—C15—O3—C14 | 58.57 (15) |
C7—C8—C9—C10 | −0.1 (2) | C13—C14—O3—C15 | −58.42 (15) |
C8—C9—C10—C11 | 0.8 (2) | | |
Symmetry code: (i) −x+1, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14A···N1ii | 0.99 | 2.72 | 3.4728 (18) | 133 |
C5—H5···O3 | 0.95 | 2.43 | 3.3821 (16) | 178 |
C15—H15B···O2iii | 0.99 | 2.69 | 3.5146 (18) | 141 |
C14—H14B···N1iv | 0.99 | 2.66 | 3.5697 (18) | 153 |
C13—H13A···O3ii | 0.99 | 2.70 | 3.5138 (18) | 140 |
Symmetry codes: (ii) x, y+1, z; (iii) x, y−1, z; (iv) −x+3/2, y+1/2, −z+1/2. |
Interplanar angles and centroid-to-centroid distances (°, Å) of POPOP in
(I) and in its 1,4-dioxane inclusion analogue, (II) top | (I) | | (II) | |
| Angle | Distance | Angle | Distance |
A/B | 3.89 (19) | 3.72 | 3.77 (20) | 3.69 |
B/C | 6.92 (10) | 3.74 | 11.54 (9) | 4.08 |
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