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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o518.
Published online 2008 January 25. doi:  10.1107/S1600536807068444
PMCID: PMC2960160

1-[(Diethyl­amino­carbon­yl)meth­yl]-2-[hydr­oxy(6-methoxy­quinolin-4-yl)meth­yl]-5-vinyl-1-azoniabicyclo­[2.2.2]octane chloride monohydrate

Abstract

In the title compound, C26H36N3O3 +·Cl·H2O, the mol­ecular structure of the cation is stabilized by a number of C—H(...)O intra­molecular inter­actions. In the crystal structure, O—H(...)Cl and C—H(...)Cl hydrogen bonds link the ions into a ribbon-like structure along the a axis.

Related literature

For related structures, see: Oleksyn et al. (1979 [triangle]); Zhang et al. (2006 [triangle]).

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Object name is e-64-0o518-scheme1.jpg

Experimental

Crystal data

  • C26H36N3O3 +·Cl·H2O
  • M r = 492.04
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o518-efi1.jpg
  • a = 8.2213 (12) Å
  • b = 17.441 (3) Å
  • c = 18.161 (3) Å
  • V = 2604.0 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.18 mm−1
  • T = 292 K
  • 0.24 × 0.20 × 0.16 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.938, T max = 0.973
  • 15334 measured reflections
  • 5361 independent reflections
  • 3043 reflections with I > 2σ(I)
  • R int = 0.061

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.111
  • S = 0.99
  • 5361 reflections
  • 311 parameters
  • H-atom parameters constrained
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.18 e Å−3
  • Absolute structure: Flack (1983 [triangle]), with 2317 Friedel pairs
  • Flack parameter: 0.14 (9)

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Bruker, 1999 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807068444/ci2541sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068444/ci2541Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge financial support from the Youth Foundation of Jiangnan University (grant No. 104000-52210691).

supplementary crystallographic information

Comment

In the title compound (Fig. 1), the quinoline ring system is planar with a maximum deviation of 0.026 (3) Å for atom C8. Bond lengths and angles are comparable to those observed in a related cinchonine structure (Oleksyn et al., 1979) but the molecules differ slightly in the relative orientations of azoniabicyclo[2.2.2]octane and quinoline units.

The structure of cation is stabilized by a number of C—H···O intramolecular interactions. In the crystal structure O—H···Cl, C—H···Cl and Ow···Cl interactions link the ions into a ribbon along the a axis (Fig.2). Similar packing arrangement is found in the structure of a related cinchonine quaternary salt (Zhang et al., 2006).

Experimental

The title compound was prepared by the reaction of 2-chloro-N,N-diethylacetamide (3 mmol) with quinine (2 mmol) in acetone (5 ml) refluxed for 5 h under a N2 atmosphere. The resulting precipitate was isolated by filtration, washed, dried, and recrystallized from Et2O and CH2Cl2 (7:1). Single crystals suitable for X-ray diffraction study were obtained from CH2Cl2 by slow evaporation at room temperature.

Refinement

H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with O—H = 0.82 Å, C—H = 0.93–0.98 Å, and Uiso(H) = 1.5Ueq(OOH, CCH3) or 1.2Ueq(C). Each methyl group was allowed to rotate freely about its C—C bond. H-atoms bound to the oxygen atom of the water molecule could not be located from difference Fourier maps.

Figures

Fig. 1.
The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids. Water molecule has been omitted for clarity.
Fig. 2.
The molecular packing of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonding have been omitted.

Crystal data

C26H36N3O3+·Cl·H2OF000 = 1056
Mr = 492.04Dx = 1.255 Mg m3
Orthorhombic, P212121Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2754 reflections
a = 8.2213 (12) Åθ = 2.3–21.7º
b = 17.441 (3) ŵ = 0.18 mm1
c = 18.161 (3) ÅT = 292 K
V = 2604.0 (7) Å3Block, colourless
Z = 40.24 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer5361 independent reflections
Radiation source: fine-focus sealed tube3043 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.062
T = 292 Kθmax = 26.5º
[var phi] and ω scansθmin = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −6→10
Tmin = 0.938, Tmax = 0.973k = −21→21
15334 measured reflectionsl = −19→22

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.048  w = 1/[σ2(Fo2) + (0.0381P)2 + 0.4431P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.111(Δ/σ)max = 0.001
S = 1.00Δρmax = 0.15 e Å3
5361 reflectionsΔρmin = −0.18 e Å3
311 parametersExtinction correction: none
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 2317 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.14 (9)

Special details

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)

xyzUiso*/Ueq
O10.3225 (4)0.93582 (15)0.56437 (14)0.0753 (8)
O20.4216 (3)0.66267 (12)0.82251 (11)0.0479 (6)
H20.35250.67370.85330.072*
O30.5222 (3)0.90203 (12)0.78329 (11)0.0526 (6)
N20.6959 (3)0.76896 (13)0.82281 (11)0.0354 (6)
N30.4329 (4)0.92548 (14)0.89798 (14)0.0464 (7)
C10.3147 (4)0.73809 (18)0.63577 (14)0.0376 (7)
C20.3419 (4)0.81809 (18)0.63353 (16)0.0410 (8)
H2A0.38780.84260.67390.049*
C30.3012 (5)0.8596 (2)0.57254 (18)0.0539 (9)
C40.2293 (5)0.8234 (2)0.51162 (18)0.0663 (12)
H40.20160.85230.47050.080*
C50.2000 (5)0.7482 (3)0.51186 (17)0.0637 (10)
H50.15150.72540.47110.076*
C60.2417 (4)0.7029 (2)0.57315 (17)0.0470 (9)
N10.2080 (4)0.62659 (18)0.56833 (16)0.0588 (8)
C70.2426 (4)0.5857 (2)0.6256 (2)0.0548 (10)
H70.22060.53350.62320.066*
C80.3111 (4)0.61412 (19)0.69128 (17)0.0474 (8)
H80.32990.58140.73080.057*
C90.3497 (4)0.69032 (18)0.69654 (15)0.0363 (8)
C100.4145 (7)0.9754 (2)0.6174 (3)0.1019 (17)
H10A0.51590.94940.62500.153*
H10B0.35520.97730.66290.153*
H10C0.43511.02670.60050.153*
C110.4261 (4)0.72014 (16)0.76742 (14)0.0328 (7)
H110.36440.76480.78450.039*
C120.6021 (3)0.74435 (18)0.75294 (13)0.0320 (7)
H120.59830.78900.72020.038*
C130.7026 (4)0.68341 (19)0.71416 (16)0.0414 (8)
H13A0.69180.68920.66130.050*
H13B0.66320.63290.72760.050*
C140.8815 (4)0.6912 (2)0.73606 (18)0.0486 (9)
H140.95060.66140.70270.058*
C150.9306 (4)0.7755 (2)0.73507 (17)0.0527 (9)
H151.04700.77750.74660.063*
C160.8411 (4)0.81627 (19)0.79803 (16)0.0440 (8)
H16A0.91480.82370.83910.053*
H16B0.80450.86630.78150.053*
C190.8954 (5)0.6608 (2)0.81431 (18)0.0571 (10)
H19A1.00310.67150.83360.069*
H19B0.87930.60570.81460.069*
C200.7671 (4)0.69938 (17)0.86258 (16)0.0464 (9)
H20A0.81600.71550.90870.056*
H20B0.68100.66310.87370.056*
C170.9092 (5)0.8107 (3)0.6606 (2)0.0611 (11)
H170.94960.78220.62140.073*
C180.8428 (6)0.8751 (3)0.6433 (2)0.0897 (15)
H18A0.79990.90650.67990.108*
H18B0.83770.89020.59430.108*
C210.5994 (4)0.81309 (17)0.87826 (14)0.0370 (7)
H21A0.67140.82800.91810.044*
H21B0.51720.77940.89880.044*
C220.5158 (4)0.88459 (17)0.84909 (17)0.0388 (8)
C230.3385 (5)0.9913 (2)0.8714 (2)0.0639 (11)
H23A0.39631.01520.83090.077*
H23B0.32971.02880.91070.077*
C240.1710 (6)0.9696 (3)0.8462 (3)0.116 (2)
H24A0.11160.94790.88660.174*
H24B0.17880.93270.80710.174*
H24C0.11541.01450.82870.174*
C250.4319 (5)0.9119 (2)0.97795 (17)0.0571 (10)
H25A0.45900.85870.98740.069*
H25B0.32330.92100.99680.069*
C260.5499 (6)0.9624 (2)1.0182 (2)0.0776 (14)
H26A0.52981.01501.00560.116*
H26B0.65890.94891.00440.116*
H26C0.53650.95561.07030.116*
Cl10.19903 (11)0.74211 (6)0.93207 (4)0.0619 (3)
O40.9536 (5)0.8684 (2)−0.01438 (18)0.1224 (12)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.102 (2)0.0584 (17)0.0655 (16)0.0077 (16)−0.0188 (19)0.0180 (14)
O20.0541 (17)0.0496 (14)0.0399 (12)−0.0007 (12)0.0049 (12)0.0114 (11)
O30.0734 (18)0.0461 (14)0.0383 (13)0.0105 (13)0.0025 (13)0.0030 (11)
N20.0321 (14)0.0401 (15)0.0341 (12)0.0020 (13)0.0009 (13)−0.0032 (11)
N30.055 (2)0.0343 (16)0.0500 (16)0.0071 (15)0.0124 (15)−0.0005 (12)
C10.0311 (17)0.048 (2)0.0341 (15)0.0033 (17)0.0008 (15)−0.0072 (15)
C20.040 (2)0.049 (2)0.0342 (17)0.0088 (17)−0.0035 (16)0.0010 (15)
C30.060 (2)0.055 (2)0.046 (2)0.012 (2)−0.001 (2)0.0022 (18)
C40.082 (3)0.078 (3)0.0381 (19)0.016 (3)−0.009 (2)0.005 (2)
C50.073 (3)0.080 (3)0.0382 (18)0.009 (3)−0.015 (2)−0.009 (2)
C60.044 (2)0.055 (2)0.0419 (19)0.0060 (17)−0.0009 (17)−0.0078 (17)
N10.0565 (19)0.065 (2)0.0547 (18)0.0069 (17)−0.0075 (18)−0.0142 (17)
C70.045 (2)0.050 (2)0.069 (2)−0.0047 (18)−0.001 (2)−0.020 (2)
C80.0370 (19)0.051 (2)0.054 (2)−0.0063 (18)0.0021 (18)−0.0017 (16)
C90.0263 (18)0.0421 (19)0.0403 (17)−0.0032 (15)0.0043 (15)−0.0049 (15)
C100.146 (5)0.049 (3)0.111 (4)−0.002 (3)−0.038 (4)0.019 (3)
C110.0324 (18)0.0349 (17)0.0310 (15)0.0007 (14)0.0006 (14)0.0008 (13)
C120.0288 (16)0.0425 (18)0.0247 (13)0.0041 (15)−0.0030 (13)−0.0017 (13)
C130.0324 (18)0.051 (2)0.0407 (17)0.0089 (18)−0.0004 (17)−0.0122 (15)
C140.032 (2)0.062 (2)0.051 (2)0.0098 (18)−0.0014 (17)−0.0197 (18)
C150.0279 (19)0.073 (3)0.057 (2)−0.0010 (19)0.0005 (18)−0.0126 (19)
C160.034 (2)0.053 (2)0.0451 (18)−0.0070 (17)−0.0019 (17)−0.0046 (16)
C190.048 (2)0.058 (2)0.065 (2)0.0162 (19)−0.016 (2)−0.0141 (19)
C200.052 (2)0.044 (2)0.0426 (18)0.0094 (17)−0.0153 (18)−0.0010 (15)
C170.043 (2)0.086 (3)0.054 (2)−0.013 (2)0.014 (2)−0.004 (2)
C180.110 (4)0.095 (4)0.064 (3)−0.020 (3)0.022 (3)0.009 (3)
C210.0422 (19)0.0399 (18)0.0288 (14)0.0031 (16)−0.0018 (15)−0.0058 (14)
C220.040 (2)0.0332 (18)0.0427 (19)−0.0022 (16)−0.0007 (16)−0.0042 (15)
C230.075 (3)0.040 (2)0.077 (3)0.020 (2)0.010 (2)0.0034 (19)
C240.057 (3)0.106 (4)0.186 (6)0.015 (3)0.008 (4)0.059 (4)
C250.076 (3)0.051 (2)0.0440 (19)0.003 (2)0.023 (2)−0.0046 (17)
C260.117 (4)0.061 (3)0.055 (2)−0.019 (3)−0.001 (3)−0.0084 (19)
Cl10.0504 (5)0.0839 (7)0.0515 (5)−0.0123 (5)0.0083 (5)−0.0087 (5)
O40.128 (3)0.127 (3)0.113 (2)−0.002 (2)0.014 (2)−0.004 (2)

Geometric parameters (Å, °)

O1—C31.349 (4)C13—C141.529 (4)
O1—C101.406 (5)C13—H13A0.97
O2—C111.417 (3)C13—H13B0.97
O2—H20.82C14—C191.521 (5)
O3—C221.234 (3)C14—C151.525 (5)
N2—C211.495 (3)C14—H140.98
N2—C161.519 (4)C15—C171.496 (5)
N2—C201.529 (4)C15—C161.535 (4)
N2—C121.546 (3)C15—H150.98
N3—C221.327 (4)C16—H16A0.97
N3—C231.468 (4)C16—H16B0.97
N3—C251.472 (4)C19—C201.528 (4)
C1—C91.412 (4)C19—H19A0.97
C1—C21.414 (4)C19—H19B0.97
C1—C61.425 (4)C20—H20A0.97
C2—C31.365 (4)C20—H20B0.97
C2—H2A0.93C17—C181.287 (5)
C3—C41.405 (5)C17—H170.93
C4—C51.333 (5)C18—H18A0.93
C4—H40.93C18—H18B0.93
C5—C61.407 (5)C21—C221.519 (4)
C5—H50.93C21—H21A0.97
C6—N11.363 (4)C21—H21B0.97
N1—C71.293 (4)C23—C241.500 (6)
C7—C81.409 (4)C23—H23A0.97
C7—H70.93C23—H23B0.97
C8—C91.370 (4)C24—H24A0.96
C8—H80.93C24—H24B0.96
C9—C111.524 (4)C24—H24C0.96
C10—H10A0.96C25—C261.500 (5)
C10—H10B0.96C25—H25A0.97
C10—H10C0.96C25—H25B0.97
C11—C121.530 (4)C26—H26A0.96
C11—H110.98C26—H26B0.96
C12—C131.519 (4)C26—H26C0.96
C12—H120.98
C3—O1—C10118.6 (3)C19—C14—H14110.5
C11—O2—H2109.5C15—C14—H14110.5
C21—N2—C16109.7 (2)C13—C14—H14110.5
C21—N2—C20107.1 (2)C17—C15—C14112.1 (3)
C16—N2—C20105.7 (2)C17—C15—C16115.2 (3)
C21—N2—C12115.5 (2)C14—C15—C16108.2 (3)
C16—N2—C12107.4 (2)C17—C15—H15107.0
C20—N2—C12111.0 (2)C14—C15—H15107.0
C22—N3—C23118.2 (3)C16—C15—H15107.0
C22—N3—C25125.2 (3)N2—C16—C15110.2 (3)
C23—N3—C25116.6 (3)N2—C16—H16A109.6
C9—C1—C2124.9 (3)C15—C16—H16A109.6
C9—C1—C6117.1 (3)N2—C16—H16B109.6
C2—C1—C6117.9 (3)C15—C16—H16B109.6
C3—C2—C1120.6 (3)H16A—C16—H16B108.1
C3—C2—H2A119.7C14—C19—C20109.3 (3)
C1—C2—H2A119.7C14—C19—H19A109.8
O1—C3—C2125.5 (3)C20—C19—H19A109.8
O1—C3—C4114.3 (3)C14—C19—H19B109.8
C2—C3—C4120.2 (3)C20—C19—H19B109.8
C5—C4—C3121.1 (3)H19A—C19—H19B108.3
C5—C4—H4119.5C19—C20—N2110.0 (2)
C3—C4—H4119.5C19—C20—H20A109.7
C4—C5—C6120.7 (3)N2—C20—H20A109.7
C4—C5—H5119.6C19—C20—H20B109.7
C6—C5—H5119.6N2—C20—H20B109.7
N1—C6—C5116.6 (3)H20A—C20—H20B108.2
N1—C6—C1123.9 (3)C18—C17—C15129.0 (4)
C5—C6—C1119.5 (3)C18—C17—H17115.5
C7—N1—C6116.3 (3)C15—C17—H17115.5
N1—C7—C8125.1 (3)C17—C18—H18A120.0
N1—C7—H7117.5C17—C18—H18B120.0
C8—C7—H7117.5H18A—C18—H18B120.0
C9—C8—C7119.5 (3)N2—C21—C22115.3 (2)
C9—C8—H8120.2N2—C21—H21A108.4
C7—C8—H8120.2C22—C21—H21A108.4
C8—C9—C1118.1 (3)N2—C21—H21B108.4
C8—C9—C11119.1 (3)C22—C21—H21B108.4
C1—C9—C11122.9 (3)H21A—C21—H21B107.5
O1—C10—H10A109.5O3—C22—N3122.5 (3)
O1—C10—H10B109.5O3—C22—C21121.4 (3)
H10A—C10—H10B109.5N3—C22—C21116.1 (3)
O1—C10—H10C109.5N3—C23—C24112.9 (3)
H10A—C10—H10C109.5N3—C23—H23A109.0
H10B—C10—H10C109.5C24—C23—H23A109.0
O2—C11—C9110.1 (2)N3—C23—H23B109.0
O2—C11—C12110.0 (2)C24—C23—H23B109.0
C9—C11—C12109.8 (2)H23A—C23—H23B107.8
O2—C11—H11109.0C23—C24—H24A109.5
C9—C11—H11109.0C23—C24—H24B109.5
C12—C11—H11109.0H24A—C24—H24B109.5
C13—C12—C11113.6 (3)C23—C24—H24C109.5
C13—C12—N2107.7 (2)H24A—C24—H24C109.5
C11—C12—N2114.0 (2)H24B—C24—H24C109.5
C13—C12—H12107.0N3—C25—C26112.5 (3)
C11—C12—H12107.0N3—C25—H25A109.1
N2—C12—H12107.0C26—C25—H25A109.1
C12—C13—C14109.9 (2)N3—C25—H25B109.1
C12—C13—H13A109.7C26—C25—H25B109.1
C14—C13—H13A109.7H25A—C25—H25B107.8
C12—C13—H13B109.7C25—C26—H26A109.5
C14—C13—H13B109.7C25—C26—H26B109.5
H13A—C13—H13B108.2H26A—C26—H26B109.5
C19—C14—C15109.1 (3)C25—C26—H26C109.5
C19—C14—C13106.5 (3)H26A—C26—H26C109.5
C15—C14—C13109.7 (3)H26B—C26—H26C109.5
C9—C1—C2—C3−178.8 (3)C16—N2—C12—C11−160.6 (2)
C6—C1—C2—C3−1.0 (5)C20—N2—C12—C1184.3 (3)
C10—O1—C3—C29.8 (6)C11—C12—C13—C14−150.9 (3)
C10—O1—C3—C4−170.9 (4)N2—C12—C13—C14−23.6 (3)
C1—C2—C3—O1−179.6 (3)C12—C13—C14—C1974.2 (3)
C1—C2—C3—C41.0 (5)C12—C13—C14—C15−43.7 (4)
O1—C3—C4—C5−179.7 (4)C19—C14—C15—C17−176.2 (3)
C2—C3—C4—C5−0.3 (6)C13—C14—C15—C17−59.8 (4)
C3—C4—C5—C6−0.5 (6)C19—C14—C15—C16−48.0 (3)
C4—C5—C6—N1−179.7 (4)C13—C14—C15—C1668.3 (3)
C4—C5—C6—C10.5 (5)C21—N2—C16—C15−173.8 (2)
C9—C1—C6—N1−1.6 (5)C20—N2—C16—C1571.1 (3)
C2—C1—C6—N1−179.6 (3)C12—N2—C16—C15−47.5 (3)
C9—C1—C6—C5178.2 (3)C17—C15—C16—N2107.2 (3)
C2—C1—C6—C50.2 (4)C14—C15—C16—N2−19.1 (3)
C5—C6—N1—C7−178.2 (3)C15—C14—C19—C2067.4 (4)
C1—C6—N1—C71.6 (5)C13—C14—C19—C20−50.9 (4)
C6—N1—C7—C80.1 (5)C14—C19—C20—N2−14.0 (4)
N1—C7—C8—C9−1.8 (5)C21—N2—C20—C19−168.1 (3)
C7—C8—C9—C11.7 (5)C16—N2—C20—C19−51.2 (3)
C7—C8—C9—C11−179.1 (3)C12—N2—C20—C1964.9 (3)
C2—C1—C9—C8177.7 (3)C14—C15—C17—C18133.4 (5)
C6—C1—C9—C8−0.1 (4)C16—C15—C17—C189.1 (6)
C2—C1—C9—C11−1.5 (5)C16—N2—C21—C2266.6 (3)
C6—C1—C9—C11−179.4 (3)C20—N2—C21—C22−179.1 (3)
C8—C9—C11—O2−9.1 (4)C12—N2—C21—C22−55.0 (3)
C1—C9—C11—O2170.2 (3)C23—N3—C22—O33.5 (5)
C8—C9—C11—C12112.2 (3)C25—N3—C22—O3−174.3 (3)
C1—C9—C11—C12−68.6 (4)C23—N3—C22—C21−174.8 (3)
O2—C11—C12—C1370.3 (3)C25—N3—C22—C217.4 (5)
C9—C11—C12—C13−51.0 (3)N2—C21—C22—O33.3 (4)
O2—C11—C12—N2−53.6 (3)N2—C21—C22—N3−178.4 (3)
C9—C11—C12—N2−175.0 (2)C22—N3—C23—C2486.3 (4)
C21—N2—C12—C13−164.9 (2)C25—N3—C23—C24−95.7 (4)
C16—N2—C12—C1372.3 (3)C22—N3—C25—C2696.8 (4)
C20—N2—C12—C13−42.8 (3)C23—N3—C25—C26−81.1 (4)
C21—N2—C12—C11−37.8 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···Cl10.822.253.038 (2)161
C19—H19A···Cl1i0.972.703.580 (4)150
C20—H20B···O20.972.333.001 (4)126
C21—H21B···Cl10.972.763.650 (3)152
C21—H21B···O20.972.583.169 (4)119

Symmetry codes: (i) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2541).

References

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  • Bruker (1999). SAINT (Version 5.2) and SHELXTL (Version 5.10). Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Oleksyn, B., Lebioda, Ł. & Ciechanowicz-Rutkowska, M. (1979). Acta Cryst. B35, 440–444.
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  • Zhang, L. P., Chen, X. D., Lv, J. & Wang, Y. M. (2006). J. Mol. Struct.789, 169–176.

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