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The crystal structures of 8-phen­oxy­carbonyl-1,8-diaza­bicyclo­[5.4.0]undec-7-enium chloride, C16H21N2O2+·Cl, (I), and 8-meth­oxy­carbonyl-1,8-diaza­bicyclo­[5.4.0]undec-7-enium chloride monohydrate, C11H19N2O2+·Cl·H2O, (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 P21/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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113005970/cu3025sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113005970/cu3025Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113005970/cu3025IIsup3.hkl
Contains datablock II

CCDC references: 934627; 934628

Computing details top

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+·ClF(000) = 656
Mr = 308.81Dx = 1.352 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9878 reflections
a = 10.1805 (2) Åθ = 2–29°
b = 14.5849 (4) ŵ = 0.26 mm1
c = 10.3843 (2) ÅT = 298 K
β = 100.404 (1)°Prism, white
V = 1516.53 (6) Å30.90 × 0.40 × 0.27 mm
Z = 4
Data collection top
Bruker Kappa APEXII area-detector
diffractometer
3554 reflections with I > 2.0σ(I)
Graphite monochromatorRint = 0.027
φ and ω scansθmax = 31.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008)
h = 1412
Tmin = 0.91, Tmax = 1.00k = 2121
39738 measured reflectionsl = 1515
4837 independent reflections
Refinement top
Refinement on FPrimary atom site location: difference Fourier map
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.042H-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 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.13 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.85069 (4)0.10490 (2)0.20583 (3)0.0480
O10.40154 (8)0.55211 (6)0.07040 (8)0.0385
O20.32680 (9)0.40625 (6)0.07409 (9)0.0417
N10.15437 (10)0.57211 (7)0.28431 (9)0.0344
N80.25368 (10)0.48888 (6)0.10362 (9)0.0337
C20.07738 (13)0.65225 (9)0.34609 (13)0.0416
C30.06487 (13)0.65452 (10)0.31996 (15)0.0469
C40.07413 (13)0.69317 (9)0.18631 (15)0.0456
C50.00636 (14)0.63953 (9)0.07298 (14)0.0429
C60.15843 (12)0.64129 (8)0.07089 (12)0.0365
C70.19496 (10)0.56724 (8)0.15804 (10)0.0304
C90.24339 (16)0.40367 (8)0.18216 (12)0.0452
C100.27039 (15)0.42780 (10)0.31587 (13)0.0458
C110.16987 (15)0.49768 (9)0.37692 (12)0.0444
C120.33536 (10)0.48952 (8)0.02219 (10)0.0312
C130.41693 (11)0.38161 (8)0.18820 (11)0.0337
C140.41560 (13)0.42385 (9)0.30592 (13)0.0420
C150.50279 (16)0.39026 (11)0.41462 (14)0.0515
C160.58553 (14)0.31721 (12)0.40372 (15)0.0534
C170.58127 (15)0.27437 (11)0.28559 (17)0.0553
C180.49621 (14)0.30707 (10)0.17600 (14)0.0473
H210.07760.64690.44030.0502*
H220.12330.70880.31450.0475*
H310.10150.59290.32920.0554*
H320.11470.69360.38830.0556*
H410.04040.75570.18210.0533*
H420.16770.69340.17780.0562*
H510.02450.57620.07590.0494*
H520.00810.66660.00760.0519*
H610.20250.63210.01480.0441*
H620.18260.70010.10090.0452*
H910.30830.36070.13920.0561*
H920.15540.37940.18700.0547*
H1010.36220.45220.30560.0558*
H1020.26010.37420.37190.0545*
H1110.08110.46870.40140.0531*
H1120.19710.52530.45130.0528*
H1410.35910.47370.31090.0504*
H1510.50620.41870.49460.0642*
H1610.64670.29700.47710.0649*
H1710.63470.22310.27630.0673*
H1810.48940.27990.09520.0582*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.05566 (19)0.04221 (17)0.04751 (17)0.00742 (14)0.01309 (13)0.00748 (13)
O10.0386 (4)0.0369 (4)0.0369 (4)0.0034 (3)0.0014 (3)0.0004 (3)
O20.0431 (4)0.0390 (4)0.0375 (4)0.0079 (3)0.0077 (3)0.0104 (3)
N10.0391 (5)0.0336 (5)0.0287 (4)0.0027 (4)0.0007 (4)0.0026 (4)
N80.0398 (5)0.0300 (4)0.0285 (4)0.0003 (4)0.0015 (4)0.0010 (3)
C20.0483 (7)0.0378 (6)0.0354 (6)0.0015 (5)0.0010 (5)0.0104 (5)
C30.0392 (6)0.0412 (7)0.0540 (8)0.0027 (5)0.0085 (5)0.0114 (6)
C40.0341 (6)0.0377 (6)0.0643 (8)0.0007 (5)0.0069 (5)0.0102 (6)
C50.0449 (6)0.0399 (6)0.0456 (7)0.0046 (5)0.0130 (5)0.0058 (5)
C60.0407 (6)0.0320 (5)0.0344 (5)0.0022 (4)0.0001 (4)0.0017 (4)
C70.0300 (5)0.0306 (5)0.0290 (5)0.0038 (4)0.0011 (4)0.0018 (4)
C90.0664 (8)0.0302 (6)0.0352 (6)0.0003 (5)0.0007 (5)0.0039 (5)
C100.0527 (7)0.0459 (7)0.0387 (6)0.0021 (6)0.0083 (5)0.0081 (5)
C110.0588 (8)0.0465 (7)0.0269 (5)0.0012 (6)0.0045 (5)0.0031 (5)
C120.0287 (5)0.0342 (5)0.0295 (5)0.0011 (4)0.0023 (4)0.0026 (4)
C130.0315 (5)0.0345 (6)0.0334 (5)0.0011 (4)0.0013 (4)0.0080 (4)
C140.0434 (6)0.0417 (6)0.0397 (6)0.0080 (5)0.0045 (5)0.0024 (5)
C150.0598 (8)0.0596 (9)0.0332 (6)0.0009 (7)0.0030 (5)0.0061 (6)
C160.0411 (7)0.0638 (9)0.0528 (8)0.0058 (6)0.0017 (6)0.0286 (7)
C170.0463 (7)0.0517 (8)0.0697 (10)0.0177 (6)0.0153 (7)0.0187 (7)
C180.0522 (7)0.0451 (7)0.0465 (7)0.0070 (6)0.0140 (6)0.0016 (6)
Geometric parameters (Å, º) top
O1—C121.1900 (14)C6—H610.931
O2—C121.3379 (14)C6—H620.960
O2—C131.4080 (13)C9—C101.5050 (19)
N1—C21.4868 (15)C9—H910.960
N1—C71.3036 (14)C9—H920.956
N1—C111.4776 (16)C10—C111.501 (2)
N8—C71.3642 (14)C10—H1010.987
N8—C91.4799 (15)C10—H1020.968
N8—C121.4162 (14)C11—H1110.989
C2—C31.521 (2)C11—H1120.956
C2—H210.982C13—C141.3712 (18)
C2—H220.975C13—C181.3733 (18)
C3—C41.517 (2)C14—C151.3929 (19)
C3—H310.971C14—H1410.934
C3—H320.977C15—C161.376 (2)
C4—C51.5232 (18)C15—H1510.924
C4—H410.972C16—C171.370 (2)
C4—H420.972C16—H1610.940
C5—C61.5446 (18)C17—C181.384 (2)
C5—H510.974C17—H1710.939
C5—H520.960C18—H1810.919
C6—C71.4984 (16)
C12—O2—C13119.39 (9)N8—C9—C10107.79 (11)
C2—N1—C7121.57 (10)N8—C9—H91108.5
C2—N1—C11114.00 (10)C10—C9—H91110.9
C7—N1—C11124.26 (10)N8—C9—H92108.2
C7—N8—C9119.55 (9)C10—C9—H92111.3
C7—N8—C12121.13 (9)H91—C9—H92110.0
C9—N8—C12119.03 (9)C9—C10—C11108.92 (11)
N1—C2—C3112.63 (10)C9—C10—H101108.2
N1—C2—H21105.8C11—C10—H101111.2
C3—C2—H21110.7C9—C10—H102110.3
N1—C2—H22109.6C11—C10—H102107.6
C3—C2—H22109.6H101—C10—H102110.6
H21—C2—H22108.4C10—C11—N1111.64 (10)
C2—C3—C4112.95 (11)C10—C11—H111109.9
C2—C3—H31108.9N1—C11—H111106.3
C4—C3—H31110.4C10—C11—H112110.7
C2—C3—H32105.6N1—C11—H112107.3
C4—C3—H32109.7H111—C11—H112110.9
H31—C3—H32109.1N8—C12—O2107.19 (9)
C3—C4—C5113.73 (11)N8—C12—O1125.91 (10)
C3—C4—H41108.1O2—C12—O1126.87 (10)
C5—C4—H41108.1O2—C13—C14121.72 (11)
C3—C4—H42108.0O2—C13—C18115.40 (11)
C5—C4—H42109.3C14—C13—C18122.58 (11)
H41—C4—H42109.6C13—C14—C15117.19 (13)
C4—C5—C6113.60 (11)C13—C14—H141120.3
C4—C5—H51109.7C15—C14—H141122.5
C6—C5—H51109.5C14—C15—C16121.05 (14)
C4—C5—H52108.5C14—C15—H151119.1
C6—C5—H52107.0C16—C15—H151119.9
H51—C5—H52108.5C15—C16—C17120.40 (12)
C5—C6—C7109.69 (10)C15—C16—H161120.1
C5—C6—H61108.6C17—C16—H161119.5
C7—C6—H61110.1C16—C17—C18119.52 (13)
C5—C6—H62109.0C16—C17—H171122.0
C7—C6—H62110.0C18—C17—H171118.5
H61—C6—H62109.3C17—C18—C13119.19 (14)
C6—C7—N8119.45 (10)C17—C18—H181122.3
C6—C7—N1120.01 (10)C13—C18—H181118.5
N8—C7—N1119.86 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H22···Cl1i0.982.943.849 (1)155
C4—H41···Cl1i0.972.843.749 (1)154
C11—H112···Cl1ii0.962.853.728 (1)154
C14—H141···Cl1iii0.932.853.771 (1)169
C10—H101···C14i0.992.893.846 (2)162
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+1/2, z1/2; (iii) x+1, y+1/2, z+1/2.
(II) 8-Methcarbonyl-1,8-diazabicyclo[5.4.0]undec-7-enium chloride monohydrate top
Crystal data top
C11H19N2O2+·Cl·H2OF(000) = 568
Mr = 264.75Dx = 1.288 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3652 reflections
a = 6.6506 (4) Åθ = 3–29°
b = 15.5432 (10) ŵ = 0.28 mm1
c = 13.2041 (10) ÅT = 298 K
β = 90.237 (5)°Plate, colourless
V = 1364.92 (16) Å30.75 × 0.65 × 0.15 mm
Z = 4
Data collection top
Bruker Kappa APEXII area-detector
diffractometer
2701 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
φ and ω scansθmax = 30.6°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008)
h = 99
Tmin = 0.83, Tmax = 0.96k = 2222
11826 measured reflectionsl = 1818
3855 independent reflections
Refinement top
Refinement on FPrimary atom site location: difference Fourier map
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.047H-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 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.16 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.41552 (7)0.87503 (3)0.61643 (4)0.0569
O10.5971 (2)0.66390 (9)0.56781 (10)0.0601
O20.79531 (19)0.73500 (9)0.67768 (11)0.0592
O30.2997 (3)1.06825 (11)0.56573 (13)0.0761
N10.2507 (2)0.59960 (10)0.80859 (10)0.0468
N80.5147 (2)0.67413 (9)0.73703 (10)0.0449
C20.1326 (3)0.51965 (14)0.82348 (15)0.0569
C30.0059 (3)0.50014 (15)0.73534 (17)0.0623
C40.0966 (3)0.45566 (15)0.64698 (19)0.0682
C50.2718 (3)0.50506 (13)0.60252 (15)0.0583
C60.4378 (3)0.52549 (11)0.67906 (13)0.0460
C70.3971 (2)0.60281 (10)0.74269 (11)0.0404
C90.5069 (3)0.73859 (13)0.82006 (13)0.0566
C100.2906 (4)0.75419 (15)0.84552 (15)0.0658
C110.1898 (3)0.67222 (15)0.87372 (14)0.0614
C120.6350 (3)0.68942 (11)0.65085 (13)0.0471
C130.9168 (3)0.76464 (16)0.5933 (2)0.0737
H210.04990.52850.88110.0685*
H220.22110.47070.83510.0671*
H310.10960.46120.75930.0745*
H320.06470.55380.71410.0741*
H410.00100.44410.59500.0823*
H420.14780.40130.67150.0816*
H510.22780.55970.57460.0700*
H520.32890.47150.54900.0700*
H610.56410.53540.64470.0552*
H620.45570.47780.72430.0549*
H910.57140.79000.79480.0680*
H920.58050.71510.87810.0674*
H1010.28420.79160.90220.0795*
H1020.22560.78100.78760.0792*
H1110.04450.67750.86790.0731*
H1120.22450.65740.94110.0738*
H1311.03300.79130.62040.1107*
H1320.94940.71540.55170.1110*
H1330.84380.80480.55360.1108*
H3010.37721.08160.52000.1136*
H3020.33681.01820.57870.1138*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0580 (3)0.0568 (2)0.0559 (2)0.0071 (2)0.00181 (18)0.00610 (19)
O10.0738 (9)0.0602 (8)0.0465 (7)0.0106 (7)0.0173 (6)0.0026 (6)
O20.0448 (7)0.0662 (8)0.0666 (8)0.0095 (6)0.0019 (6)0.0124 (6)
O30.0726 (10)0.0702 (9)0.0856 (11)0.0074 (8)0.0267 (8)0.0039 (8)
N10.0378 (7)0.0650 (9)0.0377 (6)0.0020 (6)0.0032 (5)0.0063 (6)
N80.0454 (8)0.0512 (7)0.0382 (6)0.0032 (6)0.0037 (5)0.0002 (5)
C20.0410 (10)0.0702 (12)0.0595 (10)0.0003 (8)0.0108 (8)0.0218 (9)
C30.0355 (9)0.0698 (12)0.0815 (14)0.0071 (8)0.0013 (9)0.0142 (10)
C40.0545 (12)0.0660 (12)0.0841 (14)0.0131 (9)0.0080 (10)0.0009 (11)
C50.0599 (11)0.0594 (10)0.0557 (10)0.0072 (9)0.0016 (8)0.0079 (8)
C60.0361 (8)0.0470 (8)0.0550 (9)0.0015 (6)0.0086 (7)0.0030 (7)
C70.0334 (7)0.0515 (8)0.0362 (7)0.0035 (6)0.0004 (5)0.0064 (6)
C90.0686 (12)0.0577 (10)0.0433 (8)0.0062 (9)0.0016 (8)0.0060 (7)
C100.0793 (14)0.0715 (12)0.0467 (9)0.0163 (11)0.0074 (9)0.0092 (9)
C110.0566 (11)0.0870 (14)0.0406 (9)0.0115 (10)0.0095 (7)0.0026 (9)
C120.0454 (9)0.0471 (8)0.0487 (8)0.0002 (7)0.0089 (7)0.0047 (7)
C130.0558 (13)0.0754 (14)0.0901 (15)0.0115 (10)0.0220 (11)0.0194 (12)
Geometric parameters (Å, º) top
O1—C121.192 (2)C4—H420.966
O2—C121.327 (2)C5—C61.527 (3)
O2—C131.454 (2)C5—H510.971
O3—H3010.822C5—H520.959
O3—H3020.833C6—C71.492 (2)
N1—C21.484 (2)C6—H610.969
N1—C71.309 (2)C6—H620.960
N1—C111.477 (3)C9—C101.498 (3)
N8—C71.359 (2)C9—H910.968
N8—C91.486 (2)C9—H920.978
N8—C121.414 (2)C10—C111.488 (3)
C2—C31.512 (3)C10—H1010.949
C2—H210.951C10—H1020.971
C2—H220.974C11—H1110.973
C3—C41.520 (3)C11—H1120.947
C3—H310.971C13—H1310.946
C3—H320.963C13—H1320.967
C4—C51.515 (3)C13—H1330.947
C4—H410.960
C12—O2—C13114.39 (16)C7—C6—H61107.2
H301—O3—H302101.6C5—C6—H62109.8
C2—N1—C7121.03 (16)C7—C6—H62107.1
C2—N1—C11114.61 (15)H61—C6—H62107.9
C7—N1—C11124.36 (16)C6—C7—N8121.37 (14)
C7—N8—C9119.19 (14)C6—C7—N1118.72 (15)
C7—N8—C12120.60 (14)N8—C7—N1119.82 (15)
C9—N8—C12120.12 (14)N8—C9—C10108.11 (16)
N1—C2—C3112.79 (15)N8—C9—H91106.6
N1—C2—H21107.0C10—C9—H91111.8
C3—C2—H21106.9N8—C9—H92107.9
N1—C2—H22110.8C10—C9—H92111.2
C3—C2—H22109.3H91—C9—H92111.0
H21—C2—H22109.8C9—C10—C11110.58 (18)
C2—C3—C4114.07 (17)C9—C10—H101108.8
C2—C3—H31107.8C11—C10—H101107.8
C4—C3—H31106.7C9—C10—H102108.5
C2—C3—H32107.2C11—C10—H102111.4
C4—C3—H32110.7H101—C10—H102109.6
H31—C3—H32110.3C10—C11—N1112.58 (15)
C3—C4—C5114.52 (18)C10—C11—H111110.9
C3—C4—H41109.2N1—C11—H111107.1
C5—C4—H41109.6C10—C11—H112109.6
C3—C4—H42107.4N1—C11—H112107.2
C5—C4—H42107.6H111—C11—H112109.4
H41—C4—H42108.2N8—C12—O2109.37 (15)
C4—C5—C6113.80 (17)N8—C12—O1124.49 (16)
C4—C5—H51111.1O2—C12—O1126.14 (16)
C6—C5—H51106.6O2—C13—H131107.7
C4—C5—H52108.5O2—C13—H132108.1
C6—C5—H52108.3H131—C13—H132112.2
H51—C5—H52108.4O2—C13—H133110.3
C5—C6—C7114.08 (15)H131—C13—H133109.7
C5—C6—H61110.4H132—C13—H133108.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H301···Cl1i0.822.373.192 (2)177
O3—H302···Cl10.832.343.171 (2)176
C5—H52···O1ii0.962.663.568 (3)159
C11—H112···Cl1iii0.952.683.609 (2)166
C13—H131···Cl1iv0.952.863.746 (2)157
C13—H133···O3i0.952.703.634 (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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