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Crystal structure of ethyl 2,4-di­chloro­quinoline-3-carboxyl­ate

aCentro de Graduados e Investigación en Química del Instituto, Tecnológico de, Tijuana, Apdo. Postal 1166, 22500, Tijuana, B.C., Mexico, and bInstituto de Química, Universidad Nacional Autónoma de, México, Circuito, Exterior, S. N., Ciudad Universitaria, Coyoacán, México, D. F. 04510, Mexico
*Correspondence e-mail: dchavez@tectijuana.mx

Edited by G. S. Nichol, University of Edinburgh, Scotland (Received 9 July 2015; accepted 30 October 2015; online 14 November 2015)

In the crystal structure of the title compound, C12H9Cl2NO2, the mean planes through the quinoline and carboxyl­ate groups have r.m.s. deviations of 0.006 and 0.021 Å, respectively, and form a dihedral angle of 87.06 (19)°. In the crystal, mol­ecules are linked via very weak C—H⋯O hydrogen bonds, forming chains, which propagate along the c-axis direction.

1. Related literature

For the potential of related compounds in anti-HIV treatment, see: Maartens et al. (2014[Maartens, G., Celum, C. & Lewin, S. R. (2014). Lancet, 384, 258-271.]); Hopkins et al. (2004[Hopkins, A. L., Ren, J., Milton, J., Hazen, R. J., Chan, J. H., Stuart, D. I. & Stammers, D. K. (2004). J. Med. Chem. 47, 5912-5922.]). For a related structure, see: Reyes et al. (2013[Reyes, H., Aguirre, G. & Chávez, D. (2013). Acta Cryst. E69, o1534.])

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C12H9Cl2NO2

  • Mr = 270.10

  • Monoclinic, P 21 /c

  • a = 8.5860 (4) Å

  • b = 19.9082 (11) Å

  • c = 7.1304 (4) Å

  • β = 100.262 (1)°

  • V = 1199.32 (11) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.53 mm−1

  • T = 298 K

  • 0.50 × 0.25 × 0.16 mm

2.2. Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • 6785 measured reflections

  • 2197 independent reflections

  • 1833 reflections with I > 2σ(I)

  • Rint = 0.024

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.094

  • S = 1.05

  • 2197 reflections

  • 156 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C7—H7⋯O1i 0.93 2.69 3.586 (3) 162
Symmetry code: (i) [x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2012[Bruker (2012). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2012[Bruker (2012). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Chemical context top

The HIV (human immunodeficiency virus) is responsible of the acquired immunodeficiency syndrome (AIDS). The actual treatment consists of a group of several drugs known as anti-retrovirals which inhibit important proteins for virus replication, including reverse transcriptase (Maartens et al., 2014).

As part of the synthesis of promising compounds as anti-retrovirals, Stammers and coworkers, maintaining as base structure a quinolone core, found compounds that showed activity in the inhibition of the reverse transcriptase. They obtained a dibromide quinolone in C2/C4 as an inter­mediate. After that, they were able to remove the C2 bromine in an acetic acid solution and finally, the C4 bromine was substituted by alkyl-sulfurated compounds to get the final molecules which have been proven activity against HIV (Hopkins et al., 2004),

As part of our ongoing research, we have synthesized different pyridin-2 (1H)-one analogues (Reyes et al., 2013). In this work, we developed a methodology to obtain derivatives of quinolone, with saturated and unsaturated amines in in C4 with ethyl 4-hy­droxy-2-oxo-1,2-di­hydro­quinoline-3-carboxilate as a starting material. Chlorination of the quinolone core results in the dichlorinated compound ethyl 2,4-di­chloro­quinoline-3-carboxyl­ate with a yield of 70% and a crystal structure was obtained. The inter­mediate of inter­est, the ethyl 4-chloro-2-oxo-1,2-di­hydro­quinoline-3-carboxyl­ate, was obtained after treatment of the dichlorinated compound with an acetic acid solution following the methodology described by Stammers (Hopkins et al., 2004) in >98% yield (see experimental section in supplementary material).

The structure of the compound is shown in Fig. 1. The two aromatic rings of quinoline are fused almost coaxially, with a dihedral angle between their planes of C8—C9—C10—C4= 179.21 (14)o. The carboxyl­ate group is in an anti­periplanar conformation to the quinoline with a torsion angle C12—O2—C11—C3 = -179.39 (15)°, and bonded to the quinoline over the plane C3—C11—O2 by 110.46 (14)o. The deviation of the bond length values for C2—Cl1= 1.745 (2) and C4— Cl 2= 1.7248 (16) from the standard values can be attributed for the sp2 hybridization of the quinoline ring. In the crystal, molecules are linked via O1—H7 inter­molecular hydrogen bonds forming chains propagating along the c axis direction. (Fig. 2).

Synthesis and crystallization top

The synthesis of ethyl 2,4-di­chloro­quinoline-3-carboxyl­ate and ethyl 4-chloro-2-oxo-1,2-di­hydro­quinoline-3-carboxyl­ate includes reagents and reagent grade solvents, which were used without further purification. In a 100 mL round bottom flask equipped with a magnetic stirrer was placed 500 mg of ethyl 4-hy­droxy-2-oxo-1,2-di­hydro­quinoline-3-carboxyl­ate (2.15 mmol) and 1.96 g of benzyl­tri­ethyl­ammonium chloride in 15 mL of aceto­nitrile. Under continuous stirring, 0.88 mL of the phospho­ryl chloride (9.46 mmol) was added drop by drop. The mixture was stirred at 40o C for 30 min and later at reflux for 1 h. Then, the solvent was evaporated and 15 mL of cold water was added and stirred for 1 h. Then a precipitate was obtained corresponding to a mixture of ethyl 2,4-di­chloro­quinoline-3-carboxyl­ate and ethyl 4-chloro-2-oxo-1,2-di­hydro­quinoline-3-carboxyl­ate. The precipitate was dissolved in 3 mL of di­chloro­methane-methanol (1:1, v/v). Partial evaporation leads to crystals (not suitable for X-ray diffraction) of ethyl 4-chloro-2-oxo-1,2-di­hydro­quinoline-3-carboxyl­ate (0.65 mmol, 30%). The rest corresponded to ethyl 2,4-di­chloro­quinoline-3-carboxyl­ate (1.5 mmol, 70%). The latter compound was placed in a round bottom flask of 50 mL containing acetic acid (10 mL) and water (5 mL). The mixture was stirred under reflux for 24 h. After cooling, the product was extracted with ethyl ether to afford ethyl 4-chloro-2-oxo-1,2-di­hydro­quinoline-3-carboxyl­ate (>98%).

Ethyl 2,4-di­chloro­quinoline-3-carboxyl­ate: m.p. 83-85 °C. 1H RMN (DMSO-d6): δ 8.27 (dd, J = 8.3, 0.6 Hz, H-5), 8.09 (dd, J = 8.3, 0.6 Hz, H-8), 8.03 (ddd, J = 7.7, 6.9, 1.4 Hz, H-7), 7.89 (ddd, J = 7.7, 6.9, 1.4 Hz, H-6) 4.51 (q, J = 7.1 Hz, COOCH2CH3), 1.39 (t, J = 7.1 Hz, COOCH2CH3). 13C RMN (DMSO-d6): δ 163.5, 147.2, 144.7, 141.1, 133.7, 130.2, 129.1, 127.1, 124.9, 124.3, 63.4, 14.3. IEMS m/e (int. rel): [M]+ 269 (32), [M]++2 271 (21), [M]++4 273 (3), 241 (26), 223 (100), 195 (17), 161 (28) amu.

Crystals of the title compound suitable for X-ray diffraction were obtained by dissolving 15 mg of ethyl 2,4-di­chloro­quinoline-3-carboxyl­ate in 0.5 mL of ethanol-di-ethyl ether (1:1, v / v) and placing the solution in a glass vial. The solution was allowed to stand at room temperature for 7 days and the crystals formed were filtered.

Refinement details top

The C-bound H atoms were positioned geometrically and refined using a riding model with d(C—H) = 1.00 Å, Uiso = 1.2Ueq(C) for Csp3—H, d(C—H) = 0.99 Å, Uiso = 1.2Ueq(C) for CH2 groups, d(C—H) = 0.95 Å, Uiso = 1.2Ueq(C) for aromatic C—H.

Related literature top

For the potential of related compounds in anti-HIV treatment, see: Maartens et al. (2014); Hopkins et al. (2004). For a related structure, see: Reyes et al. (2013)

Structure description top

The HIV (human immunodeficiency virus) is responsible of the acquired immunodeficiency syndrome (AIDS). The actual treatment consists of a group of several drugs known as anti-retrovirals which inhibit important proteins for virus replication, including reverse transcriptase (Maartens et al., 2014).

As part of the synthesis of promising compounds as anti-retrovirals, Stammers and coworkers, maintaining as base structure a quinolone core, found compounds that showed activity in the inhibition of the reverse transcriptase. They obtained a dibromide quinolone in C2/C4 as an inter­mediate. After that, they were able to remove the C2 bromine in an acetic acid solution and finally, the C4 bromine was substituted by alkyl-sulfurated compounds to get the final molecules which have been proven activity against HIV (Hopkins et al., 2004),

As part of our ongoing research, we have synthesized different pyridin-2 (1H)-one analogues (Reyes et al., 2013). In this work, we developed a methodology to obtain derivatives of quinolone, with saturated and unsaturated amines in in C4 with ethyl 4-hy­droxy-2-oxo-1,2-di­hydro­quinoline-3-carboxilate as a starting material. Chlorination of the quinolone core results in the dichlorinated compound ethyl 2,4-di­chloro­quinoline-3-carboxyl­ate with a yield of 70% and a crystal structure was obtained. The inter­mediate of inter­est, the ethyl 4-chloro-2-oxo-1,2-di­hydro­quinoline-3-carboxyl­ate, was obtained after treatment of the dichlorinated compound with an acetic acid solution following the methodology described by Stammers (Hopkins et al., 2004) in >98% yield (see experimental section in supplementary material).

The structure of the compound is shown in Fig. 1. The two aromatic rings of quinoline are fused almost coaxially, with a dihedral angle between their planes of C8—C9—C10—C4= 179.21 (14)o. The carboxyl­ate group is in an anti­periplanar conformation to the quinoline with a torsion angle C12—O2—C11—C3 = -179.39 (15)°, and bonded to the quinoline over the plane C3—C11—O2 by 110.46 (14)o. The deviation of the bond length values for C2—Cl1= 1.745 (2) and C4— Cl 2= 1.7248 (16) from the standard values can be attributed for the sp2 hybridization of the quinoline ring. In the crystal, molecules are linked via O1—H7 inter­molecular hydrogen bonds forming chains propagating along the c axis direction. (Fig. 2).

For the potential of related compounds in anti-HIV treatment, see: Maartens et al. (2014); Hopkins et al. (2004). For a related structure, see: Reyes et al. (2013)

Synthesis and crystallization top

The synthesis of ethyl 2,4-di­chloro­quinoline-3-carboxyl­ate and ethyl 4-chloro-2-oxo-1,2-di­hydro­quinoline-3-carboxyl­ate includes reagents and reagent grade solvents, which were used without further purification. In a 100 mL round bottom flask equipped with a magnetic stirrer was placed 500 mg of ethyl 4-hy­droxy-2-oxo-1,2-di­hydro­quinoline-3-carboxyl­ate (2.15 mmol) and 1.96 g of benzyl­tri­ethyl­ammonium chloride in 15 mL of aceto­nitrile. Under continuous stirring, 0.88 mL of the phospho­ryl chloride (9.46 mmol) was added drop by drop. The mixture was stirred at 40o C for 30 min and later at reflux for 1 h. Then, the solvent was evaporated and 15 mL of cold water was added and stirred for 1 h. Then a precipitate was obtained corresponding to a mixture of ethyl 2,4-di­chloro­quinoline-3-carboxyl­ate and ethyl 4-chloro-2-oxo-1,2-di­hydro­quinoline-3-carboxyl­ate. The precipitate was dissolved in 3 mL of di­chloro­methane-methanol (1:1, v/v). Partial evaporation leads to crystals (not suitable for X-ray diffraction) of ethyl 4-chloro-2-oxo-1,2-di­hydro­quinoline-3-carboxyl­ate (0.65 mmol, 30%). The rest corresponded to ethyl 2,4-di­chloro­quinoline-3-carboxyl­ate (1.5 mmol, 70%). The latter compound was placed in a round bottom flask of 50 mL containing acetic acid (10 mL) and water (5 mL). The mixture was stirred under reflux for 24 h. After cooling, the product was extracted with ethyl ether to afford ethyl 4-chloro-2-oxo-1,2-di­hydro­quinoline-3-carboxyl­ate (>98%).

Ethyl 2,4-di­chloro­quinoline-3-carboxyl­ate: m.p. 83-85 °C. 1H RMN (DMSO-d6): δ 8.27 (dd, J = 8.3, 0.6 Hz, H-5), 8.09 (dd, J = 8.3, 0.6 Hz, H-8), 8.03 (ddd, J = 7.7, 6.9, 1.4 Hz, H-7), 7.89 (ddd, J = 7.7, 6.9, 1.4 Hz, H-6) 4.51 (q, J = 7.1 Hz, COOCH2CH3), 1.39 (t, J = 7.1 Hz, COOCH2CH3). 13C RMN (DMSO-d6): δ 163.5, 147.2, 144.7, 141.1, 133.7, 130.2, 129.1, 127.1, 124.9, 124.3, 63.4, 14.3. IEMS m/e (int. rel): [M]+ 269 (32), [M]++2 271 (21), [M]++4 273 (3), 241 (26), 223 (100), 195 (17), 161 (28) amu.

Crystals of the title compound suitable for X-ray diffraction were obtained by dissolving 15 mg of ethyl 2,4-di­chloro­quinoline-3-carboxyl­ate in 0.5 mL of ethanol-di-ethyl ether (1:1, v / v) and placing the solution in a glass vial. The solution was allowed to stand at room temperature for 7 days and the crystals formed were filtered.

Refinement details top

The C-bound H atoms were positioned geometrically and refined using a riding model with d(C—H) = 1.00 Å, Uiso = 1.2Ueq(C) for Csp3—H, d(C—H) = 0.99 Å, Uiso = 1.2Ueq(C) for CH2 groups, d(C—H) = 0.95 Å, Uiso = 1.2Ueq(C) for aromatic C—H.

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXTL (Sheldrick, 2015); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2015); software used to prepare material for publication: SHELXTL (Sheldrick, 2015).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Crystal packing viewed along the a axis. The intermolecular C—H···O hydrogen bonds are shown as dashed lines.
Ethyl 2,4-dichloroquinoline-3-carboxylate top
Crystal data top
C12H9Cl2NO2F(000) = 552
Mr = 270.10Dx = 1.496 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.5860 (4) ÅCell parameters from 4843 reflections
b = 19.9082 (11) Åθ = 2.4–25.4°
c = 7.1304 (4) ŵ = 0.53 mm1
β = 100.262 (1)°T = 298 K
V = 1199.32 (11) Å3Prism, colourless
Z = 40.50 × 0.25 × 0.16 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
Rint = 0.024
Detector resolution: 0.83 pixels mm-1θmax = 25.4°, θmin = 2.1°
ω scansh = 1010
6785 measured reflectionsk = 2323
2197 independent reflectionsl = 88
1833 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.035 w = 1/[σ2(Fo2) + (0.052P)2 + 0.1257P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.094(Δ/σ)max = 0.001
S = 1.05Δρmax = 0.22 e Å3
2197 reflectionsΔρmin = 0.21 e Å3
156 parametersExtinction correction: SHELXL2013 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.010 (2)
Crystal data top
C12H9Cl2NO2V = 1199.32 (11) Å3
Mr = 270.10Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.5860 (4) ŵ = 0.53 mm1
b = 19.9082 (11) ÅT = 298 K
c = 7.1304 (4) Å0.50 × 0.25 × 0.16 mm
β = 100.262 (1)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
1833 reflections with I > 2σ(I)
6785 measured reflectionsRint = 0.024
2197 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.094H-atom parameters constrained
S = 1.05Δρmax = 0.22 e Å3
2197 reflectionsΔρmin = 0.21 e Å3
156 parameters
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.85142 (7)0.95554 (3)0.67524 (10)0.0847 (2)
Cl20.49224 (5)0.73357 (2)0.59388 (7)0.05637 (19)
O10.48324 (17)0.90370 (7)0.44065 (18)0.0701 (4)
O20.48524 (14)0.89699 (6)0.75480 (17)0.0565 (3)
N10.96891 (17)0.83536 (9)0.7101 (2)0.0567 (4)
C20.8376 (2)0.86809 (9)0.6757 (2)0.0514 (4)
C30.68405 (18)0.84036 (8)0.6379 (2)0.0435 (4)
C40.67539 (18)0.77181 (8)0.6378 (2)0.0415 (4)
C50.8137 (3)0.66071 (10)0.6754 (3)0.0621 (5)
H50.71870.63720.65050.075*
C60.9535 (3)0.62696 (13)0.7135 (3)0.0816 (7)
H60.95310.58020.71430.098*
C71.0976 (3)0.66121 (14)0.7514 (3)0.0838 (8)
H71.19180.63710.77790.101*
C81.1014 (2)0.72928 (13)0.7498 (3)0.0705 (6)
H81.19810.75160.77480.085*
C90.9593 (2)0.76660 (10)0.7105 (2)0.0511 (5)
C100.81366 (19)0.73162 (9)0.6738 (2)0.0451 (4)
C110.5396 (2)0.88399 (9)0.5963 (2)0.0478 (4)
C120.3434 (2)0.93853 (11)0.7367 (3)0.0674 (5)
H12A0.25750.91820.64810.081*
H12B0.36380.98280.68970.081*
C130.3010 (3)0.94358 (13)0.9279 (3)0.0858 (7)
H13A0.27210.90000.96810.129*
H13B0.21330.97380.92350.129*
H13C0.39000.96021.01660.129*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0773 (4)0.0613 (3)0.1107 (5)0.0197 (3)0.0034 (3)0.0015 (3)
Cl20.0445 (3)0.0641 (3)0.0597 (3)0.01024 (19)0.0070 (2)0.0018 (2)
O10.0713 (9)0.0848 (10)0.0506 (8)0.0213 (7)0.0009 (7)0.0096 (7)
O20.0498 (7)0.0681 (8)0.0529 (7)0.0183 (6)0.0129 (6)0.0081 (6)
N10.0395 (8)0.0795 (11)0.0508 (9)0.0050 (7)0.0070 (6)0.0022 (8)
C20.0455 (10)0.0606 (11)0.0475 (10)0.0066 (8)0.0064 (8)0.0016 (8)
C30.0393 (9)0.0544 (10)0.0367 (8)0.0011 (7)0.0069 (7)0.0000 (7)
C40.0377 (8)0.0548 (10)0.0325 (8)0.0016 (7)0.0073 (6)0.0002 (7)
C50.0719 (13)0.0630 (12)0.0520 (11)0.0133 (10)0.0128 (9)0.0027 (9)
C60.0980 (19)0.0785 (15)0.0680 (14)0.0429 (14)0.0143 (13)0.0066 (11)
C70.0768 (16)0.118 (2)0.0564 (13)0.0554 (16)0.0110 (11)0.0060 (13)
C80.0445 (11)0.120 (2)0.0476 (11)0.0239 (11)0.0085 (8)0.0009 (11)
C90.0412 (9)0.0793 (13)0.0337 (9)0.0101 (8)0.0090 (7)0.0001 (8)
C100.0451 (9)0.0608 (11)0.0301 (8)0.0100 (8)0.0088 (7)0.0016 (7)
C110.0440 (9)0.0499 (9)0.0481 (10)0.0006 (7)0.0042 (8)0.0018 (8)
C120.0544 (11)0.0706 (12)0.0778 (13)0.0229 (10)0.0136 (10)0.0079 (11)
C130.0641 (14)0.1089 (19)0.0878 (16)0.0215 (13)0.0227 (12)0.0130 (14)
Geometric parameters (Å, º) top
Cl1—C21.745 (2)C6—C71.396 (4)
Cl2—C41.7248 (16)C6—H60.9300
O1—C111.195 (2)C7—C81.356 (4)
O2—C111.323 (2)C7—H70.9300
O2—C121.459 (2)C8—C91.413 (3)
N1—C21.287 (2)C8—H80.9300
N1—C91.371 (3)C9—C101.414 (2)
C2—C31.411 (2)C12—C131.476 (3)
C3—C41.367 (2)C12—H12A0.9700
C3—C111.500 (2)C12—H12B0.9700
C4—C101.417 (2)C13—H13A0.9600
C5—C61.360 (3)C13—H13B0.9600
C5—C101.412 (3)C13—H13C0.9600
C5—H50.9300
C11—O2—C12116.84 (14)C9—C8—H8119.8
C2—N1—C9117.06 (15)N1—C9—C8118.38 (18)
N1—C2—C3126.55 (18)N1—C9—C10122.85 (15)
N1—C2—Cl1116.62 (14)C8—C9—C10118.77 (19)
C3—C2—Cl1116.83 (14)C5—C10—C9119.45 (16)
C4—C3—C2116.09 (15)C5—C10—C4124.43 (17)
C4—C3—C11122.35 (14)C9—C10—C4116.12 (16)
C2—C3—C11121.55 (15)O1—C11—O2125.64 (16)
C3—C4—C10121.33 (15)O1—C11—C3123.90 (16)
C3—C4—Cl2119.25 (12)O2—C11—C3110.46 (14)
C10—C4—Cl2119.42 (13)O2—C12—C13107.24 (16)
C6—C5—C10119.7 (2)O2—C12—H12A110.3
C6—C5—H5120.2C13—C12—H12A110.3
C10—C5—H5120.2O2—C12—H12B110.3
C5—C6—C7121.2 (2)C13—C12—H12B110.3
C5—C6—H6119.4H12A—C12—H12B108.5
C7—C6—H6119.4C12—C13—H13A109.5
C8—C7—C6120.5 (2)C12—C13—H13B109.5
C8—C7—H7119.7H13A—C13—H13B109.5
C6—C7—H7119.7C12—C13—H13C109.5
C7—C8—C9120.4 (2)H13A—C13—H13C109.5
C7—C8—H8119.8H13B—C13—H13C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O1i0.932.693.586 (3)162
Symmetry code: (i) x+1, y+3/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O1i0.932.693.586 (3)162.2
Symmetry code: (i) x+1, y+3/2, z+1/2.
 

Acknowledgements

We gratefully acknowledge support for this project by Consejo Nacional de Ciencia y Tecnología (CONACyT Grant 155029). AC and HR acknowledge support from CONACyT in the form of graduate scholarships.

References

First citationBruker (2012). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
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