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The crystal structures of 8-phenoxycarbonyl-1,8-diazabicyclo[5.4.0]undec-7-enium chloride, C
16H
21N
2O
2+·Cl
−, (I), and 8-methoxycarbonyl-1,8-diazabicyclo[5.4.0]undec-7-enium chloride monohydrate, C
11H
19N
2O
2+·Cl
−·H
2O, (II), recently reported by Carafa, Mesto & Quaranta [
Eur. J. Org. Chem. (2011), pp. 2458–2465], are analysed and discussed with a focus on crystal interaction assembly. Both compounds crystallize in the space group
P2
1/
c. The crystal packings are characterized by dimers linked through π–π stacking interactions and intermolecular nonclassical hydrogen bonds, respectively. Additional intermolecular C—H
Cl interactions [in (I) and (II)] and classical O—H
Cl hydrogen bonds [in (II)] are also evident and contribute to generating three-dimensional hydrogen-bonded networks.
Supporting information
CCDC references: 934627; 934628
For both compounds, data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).
(I) 8-Phenoxycarbonyl-1,8-diazabicyclo[5.4.0]undec-7-enium chloride
top
Crystal data top
C16H21N2O2+·Cl− | F(000) = 656 |
Mr = 308.81 | Dx = 1.352 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9878 reflections |
a = 10.1805 (2) Å | θ = 2–29° |
b = 14.5849 (4) Å | µ = 0.26 mm−1 |
c = 10.3843 (2) Å | T = 298 K |
β = 100.404 (1)° | Prism, white |
V = 1516.53 (6) Å3 | 0.90 × 0.40 × 0.27 mm |
Z = 4 | |
Data collection top
Bruker Kappa APEXII area-detector diffractometer | 3554 reflections with I > 2.0σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scans | θmax = 31.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008) | h = −14→12 |
Tmin = 0.91, Tmax = 1.00 | k = −21→21 |
39738 measured reflections | l = −15→15 |
4837 independent reflections | |
Refinement top
Refinement on F | Primary atom site location: difference Fourier map |
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) = 0.042 | H-atom parameters constrained |
S = 1.05 | Method, part 1, Chebychev polynomial, (Watkin, 1994; Prince, 1982)
[weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)2]2
Ai are:
0.623 0.530 0.324 |
3285 reflections | (Δ/σ)max = 0.0002191 |
190 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.13 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.85069 (4) | 0.10490 (2) | 0.20583 (3) | 0.0480 | |
O1 | 0.40154 (8) | 0.55211 (6) | 0.07040 (8) | 0.0385 | |
O2 | 0.32680 (9) | 0.40625 (6) | 0.07409 (9) | 0.0417 | |
N1 | 0.15437 (10) | 0.57211 (7) | −0.28431 (9) | 0.0344 | |
N8 | 0.25368 (10) | 0.48888 (6) | −0.10362 (9) | 0.0337 | |
C2 | 0.07738 (13) | 0.65225 (9) | −0.34609 (13) | 0.0416 | |
C3 | −0.06487 (13) | 0.65452 (10) | −0.31996 (15) | 0.0469 | |
C4 | −0.07413 (13) | 0.69317 (9) | −0.18631 (15) | 0.0456 | |
C5 | 0.00636 (14) | 0.63953 (9) | −0.07298 (14) | 0.0429 | |
C6 | 0.15843 (12) | 0.64129 (8) | −0.07089 (12) | 0.0365 | |
C7 | 0.19496 (10) | 0.56724 (8) | −0.15804 (10) | 0.0304 | |
C9 | 0.24339 (16) | 0.40367 (8) | −0.18216 (12) | 0.0452 | |
C10 | 0.27039 (15) | 0.42780 (10) | −0.31587 (13) | 0.0458 | |
C11 | 0.16987 (15) | 0.49768 (9) | −0.37692 (12) | 0.0444 | |
C12 | 0.33536 (10) | 0.48952 (8) | 0.02219 (10) | 0.0312 | |
C13 | 0.41693 (11) | 0.38161 (8) | 0.18820 (11) | 0.0337 | |
C14 | 0.41560 (13) | 0.42385 (9) | 0.30592 (13) | 0.0420 | |
C15 | 0.50279 (16) | 0.39026 (11) | 0.41462 (14) | 0.0515 | |
C16 | 0.58553 (14) | 0.31721 (12) | 0.40372 (15) | 0.0534 | |
C17 | 0.58127 (15) | 0.27437 (11) | 0.28559 (17) | 0.0553 | |
C18 | 0.49621 (14) | 0.30707 (10) | 0.17600 (14) | 0.0473 | |
H21 | 0.0776 | 0.6469 | −0.4403 | 0.0502* | |
H22 | 0.1233 | 0.7088 | −0.3145 | 0.0475* | |
H31 | −0.1015 | 0.5929 | −0.3292 | 0.0554* | |
H32 | −0.1147 | 0.6936 | −0.3883 | 0.0556* | |
H41 | −0.0404 | 0.7557 | −0.1821 | 0.0533* | |
H42 | −0.1677 | 0.6934 | −0.1778 | 0.0562* | |
H51 | −0.0245 | 0.5762 | −0.0759 | 0.0494* | |
H52 | −0.0081 | 0.6666 | 0.0076 | 0.0519* | |
H61 | 0.2025 | 0.6321 | 0.0148 | 0.0441* | |
H62 | 0.1826 | 0.7001 | −0.1009 | 0.0452* | |
H91 | 0.3083 | 0.3607 | −0.1392 | 0.0561* | |
H92 | 0.1554 | 0.3794 | −0.1870 | 0.0547* | |
H101 | 0.3622 | 0.4522 | −0.3056 | 0.0558* | |
H102 | 0.2601 | 0.3742 | −0.3719 | 0.0545* | |
H111 | 0.0811 | 0.4687 | −0.4014 | 0.0531* | |
H112 | 0.1971 | 0.5253 | −0.4513 | 0.0528* | |
H141 | 0.3591 | 0.4737 | 0.3109 | 0.0504* | |
H151 | 0.5062 | 0.4187 | 0.4946 | 0.0642* | |
H161 | 0.6467 | 0.2970 | 0.4771 | 0.0649* | |
H171 | 0.6347 | 0.2231 | 0.2763 | 0.0673* | |
H181 | 0.4894 | 0.2799 | 0.0952 | 0.0582* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.05566 (19) | 0.04221 (17) | 0.04751 (17) | −0.00742 (14) | 0.01309 (13) | −0.00748 (13) |
O1 | 0.0386 (4) | 0.0369 (4) | 0.0369 (4) | −0.0034 (3) | −0.0014 (3) | 0.0004 (3) |
O2 | 0.0431 (4) | 0.0390 (4) | 0.0375 (4) | −0.0079 (3) | −0.0077 (3) | 0.0104 (3) |
N1 | 0.0391 (5) | 0.0336 (5) | 0.0287 (4) | −0.0027 (4) | 0.0007 (4) | 0.0026 (4) |
N8 | 0.0398 (5) | 0.0300 (4) | 0.0285 (4) | 0.0003 (4) | −0.0015 (4) | −0.0010 (3) |
C2 | 0.0483 (7) | 0.0378 (6) | 0.0354 (6) | −0.0015 (5) | −0.0010 (5) | 0.0104 (5) |
C3 | 0.0392 (6) | 0.0412 (7) | 0.0540 (8) | −0.0027 (5) | −0.0085 (5) | 0.0114 (6) |
C4 | 0.0341 (6) | 0.0377 (6) | 0.0643 (8) | 0.0007 (5) | 0.0069 (5) | 0.0102 (6) |
C5 | 0.0449 (6) | 0.0399 (6) | 0.0456 (7) | 0.0046 (5) | 0.0130 (5) | 0.0058 (5) |
C6 | 0.0407 (6) | 0.0320 (5) | 0.0344 (5) | 0.0022 (4) | −0.0001 (4) | −0.0017 (4) |
C7 | 0.0300 (5) | 0.0306 (5) | 0.0290 (5) | −0.0038 (4) | 0.0011 (4) | 0.0018 (4) |
C9 | 0.0664 (8) | 0.0302 (6) | 0.0352 (6) | 0.0003 (5) | −0.0007 (5) | −0.0039 (5) |
C10 | 0.0527 (7) | 0.0459 (7) | 0.0387 (6) | 0.0021 (6) | 0.0083 (5) | −0.0081 (5) |
C11 | 0.0588 (8) | 0.0465 (7) | 0.0269 (5) | −0.0012 (6) | 0.0045 (5) | −0.0031 (5) |
C12 | 0.0287 (5) | 0.0342 (5) | 0.0295 (5) | 0.0011 (4) | 0.0023 (4) | 0.0026 (4) |
C13 | 0.0315 (5) | 0.0345 (6) | 0.0334 (5) | −0.0011 (4) | 0.0013 (4) | 0.0080 (4) |
C14 | 0.0434 (6) | 0.0417 (6) | 0.0397 (6) | 0.0080 (5) | 0.0045 (5) | 0.0024 (5) |
C15 | 0.0598 (8) | 0.0596 (9) | 0.0332 (6) | 0.0009 (7) | 0.0030 (5) | 0.0061 (6) |
C16 | 0.0411 (7) | 0.0638 (9) | 0.0528 (8) | 0.0058 (6) | 0.0017 (6) | 0.0286 (7) |
C17 | 0.0463 (7) | 0.0517 (8) | 0.0697 (10) | 0.0177 (6) | 0.0153 (7) | 0.0187 (7) |
C18 | 0.0522 (7) | 0.0451 (7) | 0.0465 (7) | 0.0070 (6) | 0.0140 (6) | 0.0016 (6) |
Geometric parameters (Å, º) top
O1—C12 | 1.1900 (14) | C6—H61 | 0.931 |
O2—C12 | 1.3379 (14) | C6—H62 | 0.960 |
O2—C13 | 1.4080 (13) | C9—C10 | 1.5050 (19) |
N1—C2 | 1.4868 (15) | C9—H91 | 0.960 |
N1—C7 | 1.3036 (14) | C9—H92 | 0.956 |
N1—C11 | 1.4776 (16) | C10—C11 | 1.501 (2) |
N8—C7 | 1.3642 (14) | C10—H101 | 0.987 |
N8—C9 | 1.4799 (15) | C10—H102 | 0.968 |
N8—C12 | 1.4162 (14) | C11—H111 | 0.989 |
C2—C3 | 1.521 (2) | C11—H112 | 0.956 |
C2—H21 | 0.982 | C13—C14 | 1.3712 (18) |
C2—H22 | 0.975 | C13—C18 | 1.3733 (18) |
C3—C4 | 1.517 (2) | C14—C15 | 1.3929 (19) |
C3—H31 | 0.971 | C14—H141 | 0.934 |
C3—H32 | 0.977 | C15—C16 | 1.376 (2) |
C4—C5 | 1.5232 (18) | C15—H151 | 0.924 |
C4—H41 | 0.972 | C16—C17 | 1.370 (2) |
C4—H42 | 0.972 | C16—H161 | 0.940 |
C5—C6 | 1.5446 (18) | C17—C18 | 1.384 (2) |
C5—H51 | 0.974 | C17—H171 | 0.939 |
C5—H52 | 0.960 | C18—H181 | 0.919 |
C6—C7 | 1.4984 (16) | | |
| | | |
C12—O2—C13 | 119.39 (9) | N8—C9—C10 | 107.79 (11) |
C2—N1—C7 | 121.57 (10) | N8—C9—H91 | 108.5 |
C2—N1—C11 | 114.00 (10) | C10—C9—H91 | 110.9 |
C7—N1—C11 | 124.26 (10) | N8—C9—H92 | 108.2 |
C7—N8—C9 | 119.55 (9) | C10—C9—H92 | 111.3 |
C7—N8—C12 | 121.13 (9) | H91—C9—H92 | 110.0 |
C9—N8—C12 | 119.03 (9) | C9—C10—C11 | 108.92 (11) |
N1—C2—C3 | 112.63 (10) | C9—C10—H101 | 108.2 |
N1—C2—H21 | 105.8 | C11—C10—H101 | 111.2 |
C3—C2—H21 | 110.7 | C9—C10—H102 | 110.3 |
N1—C2—H22 | 109.6 | C11—C10—H102 | 107.6 |
C3—C2—H22 | 109.6 | H101—C10—H102 | 110.6 |
H21—C2—H22 | 108.4 | C10—C11—N1 | 111.64 (10) |
C2—C3—C4 | 112.95 (11) | C10—C11—H111 | 109.9 |
C2—C3—H31 | 108.9 | N1—C11—H111 | 106.3 |
C4—C3—H31 | 110.4 | C10—C11—H112 | 110.7 |
C2—C3—H32 | 105.6 | N1—C11—H112 | 107.3 |
C4—C3—H32 | 109.7 | H111—C11—H112 | 110.9 |
H31—C3—H32 | 109.1 | N8—C12—O2 | 107.19 (9) |
C3—C4—C5 | 113.73 (11) | N8—C12—O1 | 125.91 (10) |
C3—C4—H41 | 108.1 | O2—C12—O1 | 126.87 (10) |
C5—C4—H41 | 108.1 | O2—C13—C14 | 121.72 (11) |
C3—C4—H42 | 108.0 | O2—C13—C18 | 115.40 (11) |
C5—C4—H42 | 109.3 | C14—C13—C18 | 122.58 (11) |
H41—C4—H42 | 109.6 | C13—C14—C15 | 117.19 (13) |
C4—C5—C6 | 113.60 (11) | C13—C14—H141 | 120.3 |
C4—C5—H51 | 109.7 | C15—C14—H141 | 122.5 |
C6—C5—H51 | 109.5 | C14—C15—C16 | 121.05 (14) |
C4—C5—H52 | 108.5 | C14—C15—H151 | 119.1 |
C6—C5—H52 | 107.0 | C16—C15—H151 | 119.9 |
H51—C5—H52 | 108.5 | C15—C16—C17 | 120.40 (12) |
C5—C6—C7 | 109.69 (10) | C15—C16—H161 | 120.1 |
C5—C6—H61 | 108.6 | C17—C16—H161 | 119.5 |
C7—C6—H61 | 110.1 | C16—C17—C18 | 119.52 (13) |
C5—C6—H62 | 109.0 | C16—C17—H171 | 122.0 |
C7—C6—H62 | 110.0 | C18—C17—H171 | 118.5 |
H61—C6—H62 | 109.3 | C17—C18—C13 | 119.19 (14) |
C6—C7—N8 | 119.45 (10) | C17—C18—H181 | 122.3 |
C6—C7—N1 | 120.01 (10) | C13—C18—H181 | 118.5 |
N8—C7—N1 | 119.86 (10) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H22···Cl1i | 0.98 | 2.94 | 3.849 (1) | 155 |
C4—H41···Cl1i | 0.97 | 2.84 | 3.749 (1) | 154 |
C11—H112···Cl1ii | 0.96 | 2.85 | 3.728 (1) | 154 |
C14—H141···Cl1iii | 0.93 | 2.85 | 3.771 (1) | 169 |
C10—H101···C14i | 0.99 | 2.89 | 3.846 (2) | 162 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, y+1/2, −z−1/2; (iii) −x+1, y+1/2, −z+1/2. |
(II) 8-Methcarbonyl-1,8-diazabicyclo[5.4.0]undec-7-enium chloride monohydrate
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Crystal data top
C11H19N2O2+·Cl−·H2O | F(000) = 568 |
Mr = 264.75 | Dx = 1.288 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3652 reflections |
a = 6.6506 (4) Å | θ = 3–29° |
b = 15.5432 (10) Å | µ = 0.28 mm−1 |
c = 13.2041 (10) Å | T = 298 K |
β = 90.237 (5)° | Plate, colourless |
V = 1364.92 (16) Å3 | 0.75 × 0.65 × 0.15 mm |
Z = 4 | |
Data collection top
Bruker Kappa APEXII area-detector diffractometer | 2701 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
φ and ω scans | θmax = 30.6°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008) | h = −9→9 |
Tmin = 0.83, Tmax = 0.96 | k = −22→22 |
11826 measured reflections | l = −18→18 |
3855 independent reflections | |
Refinement top
Refinement on F | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.047 | H-atom parameters constrained |
S = 1.02 | Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)2]2
Ai are:
0.871 1.05 0.637 0.264 0.809E-01 |
2457 reflections | (Δ/σ)max = 0.001 |
154 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.41552 (7) | 0.87503 (3) | 0.61643 (4) | 0.0569 | |
O1 | 0.5971 (2) | 0.66390 (9) | 0.56781 (10) | 0.0601 | |
O2 | 0.79531 (19) | 0.73500 (9) | 0.67768 (11) | 0.0592 | |
O3 | 0.2997 (3) | 1.06825 (11) | 0.56573 (13) | 0.0761 | |
N1 | 0.2507 (2) | 0.59960 (10) | 0.80859 (10) | 0.0468 | |
N8 | 0.5147 (2) | 0.67413 (9) | 0.73703 (10) | 0.0449 | |
C2 | 0.1326 (3) | 0.51965 (14) | 0.82348 (15) | 0.0569 | |
C3 | −0.0059 (3) | 0.50014 (15) | 0.73534 (17) | 0.0623 | |
C4 | 0.0966 (3) | 0.45566 (15) | 0.64698 (19) | 0.0682 | |
C5 | 0.2718 (3) | 0.50506 (13) | 0.60252 (15) | 0.0583 | |
C6 | 0.4378 (3) | 0.52549 (11) | 0.67906 (13) | 0.0460 | |
C7 | 0.3971 (2) | 0.60281 (10) | 0.74269 (11) | 0.0404 | |
C9 | 0.5069 (3) | 0.73859 (13) | 0.82006 (13) | 0.0566 | |
C10 | 0.2906 (4) | 0.75419 (15) | 0.84552 (15) | 0.0658 | |
C11 | 0.1898 (3) | 0.67222 (15) | 0.87372 (14) | 0.0614 | |
C12 | 0.6350 (3) | 0.68942 (11) | 0.65085 (13) | 0.0471 | |
C13 | 0.9168 (3) | 0.76464 (16) | 0.5933 (2) | 0.0737 | |
H21 | 0.0499 | 0.5285 | 0.8811 | 0.0685* | |
H22 | 0.2211 | 0.4707 | 0.8351 | 0.0671* | |
H31 | −0.1096 | 0.4612 | 0.7593 | 0.0745* | |
H32 | −0.0647 | 0.5538 | 0.7141 | 0.0741* | |
H41 | −0.0010 | 0.4441 | 0.5950 | 0.0823* | |
H42 | 0.1478 | 0.4013 | 0.6715 | 0.0816* | |
H51 | 0.2278 | 0.5597 | 0.5746 | 0.0700* | |
H52 | 0.3289 | 0.4715 | 0.5490 | 0.0700* | |
H61 | 0.5641 | 0.5354 | 0.6447 | 0.0552* | |
H62 | 0.4557 | 0.4778 | 0.7243 | 0.0549* | |
H91 | 0.5714 | 0.7900 | 0.7948 | 0.0680* | |
H92 | 0.5805 | 0.7151 | 0.8781 | 0.0674* | |
H101 | 0.2842 | 0.7916 | 0.9022 | 0.0795* | |
H102 | 0.2256 | 0.7810 | 0.7876 | 0.0792* | |
H111 | 0.0445 | 0.6775 | 0.8679 | 0.0731* | |
H112 | 0.2245 | 0.6574 | 0.9411 | 0.0738* | |
H131 | 1.0330 | 0.7913 | 0.6204 | 0.1107* | |
H132 | 0.9494 | 0.7154 | 0.5517 | 0.1110* | |
H133 | 0.8438 | 0.8048 | 0.5536 | 0.1108* | |
H301 | 0.3772 | 1.0816 | 0.5200 | 0.1136* | |
H302 | 0.3368 | 1.0182 | 0.5787 | 0.1138* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0580 (3) | 0.0568 (2) | 0.0559 (2) | −0.0071 (2) | 0.00181 (18) | 0.00610 (19) |
O1 | 0.0738 (9) | 0.0602 (8) | 0.0465 (7) | −0.0106 (7) | 0.0173 (6) | −0.0026 (6) |
O2 | 0.0448 (7) | 0.0662 (8) | 0.0666 (8) | −0.0095 (6) | 0.0019 (6) | 0.0124 (6) |
O3 | 0.0726 (10) | 0.0702 (9) | 0.0856 (11) | 0.0074 (8) | 0.0267 (8) | 0.0039 (8) |
N1 | 0.0378 (7) | 0.0650 (9) | 0.0377 (6) | 0.0020 (6) | 0.0032 (5) | 0.0063 (6) |
N8 | 0.0454 (8) | 0.0512 (7) | 0.0382 (6) | −0.0032 (6) | 0.0037 (5) | −0.0002 (5) |
C2 | 0.0410 (10) | 0.0702 (12) | 0.0595 (10) | 0.0003 (8) | 0.0108 (8) | 0.0218 (9) |
C3 | 0.0355 (9) | 0.0698 (12) | 0.0815 (14) | −0.0071 (8) | −0.0013 (9) | 0.0142 (10) |
C4 | 0.0545 (12) | 0.0660 (12) | 0.0841 (14) | −0.0131 (9) | −0.0080 (10) | −0.0009 (11) |
C5 | 0.0599 (11) | 0.0594 (10) | 0.0557 (10) | −0.0072 (9) | 0.0016 (8) | −0.0079 (8) |
C6 | 0.0361 (8) | 0.0470 (8) | 0.0550 (9) | 0.0015 (6) | 0.0086 (7) | 0.0030 (7) |
C7 | 0.0334 (7) | 0.0515 (8) | 0.0362 (7) | 0.0035 (6) | −0.0004 (5) | 0.0064 (6) |
C9 | 0.0686 (12) | 0.0577 (10) | 0.0433 (8) | −0.0062 (9) | −0.0016 (8) | −0.0060 (7) |
C10 | 0.0793 (14) | 0.0715 (12) | 0.0467 (9) | 0.0163 (11) | 0.0074 (9) | −0.0092 (9) |
C11 | 0.0566 (11) | 0.0870 (14) | 0.0406 (9) | 0.0115 (10) | 0.0095 (7) | −0.0026 (9) |
C12 | 0.0454 (9) | 0.0471 (8) | 0.0487 (8) | 0.0002 (7) | 0.0089 (7) | 0.0047 (7) |
C13 | 0.0558 (13) | 0.0754 (14) | 0.0901 (15) | −0.0115 (10) | 0.0220 (11) | 0.0194 (12) |
Geometric parameters (Å, º) top
O1—C12 | 1.192 (2) | C4—H42 | 0.966 |
O2—C12 | 1.327 (2) | C5—C6 | 1.527 (3) |
O2—C13 | 1.454 (2) | C5—H51 | 0.971 |
O3—H301 | 0.822 | C5—H52 | 0.959 |
O3—H302 | 0.833 | C6—C7 | 1.492 (2) |
N1—C2 | 1.484 (2) | C6—H61 | 0.969 |
N1—C7 | 1.309 (2) | C6—H62 | 0.960 |
N1—C11 | 1.477 (3) | C9—C10 | 1.498 (3) |
N8—C7 | 1.359 (2) | C9—H91 | 0.968 |
N8—C9 | 1.486 (2) | C9—H92 | 0.978 |
N8—C12 | 1.414 (2) | C10—C11 | 1.488 (3) |
C2—C3 | 1.512 (3) | C10—H101 | 0.949 |
C2—H21 | 0.951 | C10—H102 | 0.971 |
C2—H22 | 0.974 | C11—H111 | 0.973 |
C3—C4 | 1.520 (3) | C11—H112 | 0.947 |
C3—H31 | 0.971 | C13—H131 | 0.946 |
C3—H32 | 0.963 | C13—H132 | 0.967 |
C4—C5 | 1.515 (3) | C13—H133 | 0.947 |
C4—H41 | 0.960 | | |
| | | |
C12—O2—C13 | 114.39 (16) | C7—C6—H61 | 107.2 |
H301—O3—H302 | 101.6 | C5—C6—H62 | 109.8 |
C2—N1—C7 | 121.03 (16) | C7—C6—H62 | 107.1 |
C2—N1—C11 | 114.61 (15) | H61—C6—H62 | 107.9 |
C7—N1—C11 | 124.36 (16) | C6—C7—N8 | 121.37 (14) |
C7—N8—C9 | 119.19 (14) | C6—C7—N1 | 118.72 (15) |
C7—N8—C12 | 120.60 (14) | N8—C7—N1 | 119.82 (15) |
C9—N8—C12 | 120.12 (14) | N8—C9—C10 | 108.11 (16) |
N1—C2—C3 | 112.79 (15) | N8—C9—H91 | 106.6 |
N1—C2—H21 | 107.0 | C10—C9—H91 | 111.8 |
C3—C2—H21 | 106.9 | N8—C9—H92 | 107.9 |
N1—C2—H22 | 110.8 | C10—C9—H92 | 111.2 |
C3—C2—H22 | 109.3 | H91—C9—H92 | 111.0 |
H21—C2—H22 | 109.8 | C9—C10—C11 | 110.58 (18) |
C2—C3—C4 | 114.07 (17) | C9—C10—H101 | 108.8 |
C2—C3—H31 | 107.8 | C11—C10—H101 | 107.8 |
C4—C3—H31 | 106.7 | C9—C10—H102 | 108.5 |
C2—C3—H32 | 107.2 | C11—C10—H102 | 111.4 |
C4—C3—H32 | 110.7 | H101—C10—H102 | 109.6 |
H31—C3—H32 | 110.3 | C10—C11—N1 | 112.58 (15) |
C3—C4—C5 | 114.52 (18) | C10—C11—H111 | 110.9 |
C3—C4—H41 | 109.2 | N1—C11—H111 | 107.1 |
C5—C4—H41 | 109.6 | C10—C11—H112 | 109.6 |
C3—C4—H42 | 107.4 | N1—C11—H112 | 107.2 |
C5—C4—H42 | 107.6 | H111—C11—H112 | 109.4 |
H41—C4—H42 | 108.2 | N8—C12—O2 | 109.37 (15) |
C4—C5—C6 | 113.80 (17) | N8—C12—O1 | 124.49 (16) |
C4—C5—H51 | 111.1 | O2—C12—O1 | 126.14 (16) |
C6—C5—H51 | 106.6 | O2—C13—H131 | 107.7 |
C4—C5—H52 | 108.5 | O2—C13—H132 | 108.1 |
C6—C5—H52 | 108.3 | H131—C13—H132 | 112.2 |
H51—C5—H52 | 108.4 | O2—C13—H133 | 110.3 |
C5—C6—C7 | 114.08 (15) | H131—C13—H133 | 109.7 |
C5—C6—H61 | 110.4 | H132—C13—H133 | 108.8 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H301···Cl1i | 0.82 | 2.37 | 3.192 (2) | 177 |
O3—H302···Cl1 | 0.83 | 2.34 | 3.171 (2) | 176 |
C5—H52···O1ii | 0.96 | 2.66 | 3.568 (3) | 159 |
C11—H112···Cl1iii | 0.95 | 2.68 | 3.609 (2) | 166 |
C13—H131···Cl1iv | 0.95 | 2.86 | 3.746 (2) | 157 |
C13—H133···O3i | 0.95 | 2.70 | 3.634 (3) | 170 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x, −y+3/2, z+1/2; (iv) x+1, y, z. |
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