Diethyl 2,6-dihy­droxy-4-(3-nitro­phen­yl)-2,6-bis­(trifluoro­meth­yl)piperidine-3,5-dicarboxyl­ate

Fun, H.-K.; Arshad, S.; Reddy, B.P.; Vijayakumar, V.; Sarveswari, S.

doi:10.1107/S1600536811055346

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages o400-o401

doi:10.1107/S1600536811055346

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Diethyl 2,6-dihydroxy-4-(3-nitrophenyl)-2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate

Hoong-Kun Fun,^a ^*‡ Suhana Arshad,^a B. Palakshi Reddy,^b V. Vijayakumar ^b and S. Sarveswari ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India
^*Correspondence e-mail: hkfun@usm.my

(Received 16 December 2011; accepted 23 December 2011; online 14 January 2012)

In the title compound, C₁₉H₂₀F₆N₂O₈, the ethoxy and ethyl groups are disordered over two sets of sites, with occupancy ratios of 0.212 (18):0.788 (18) and 0.746 (6):0.254 (6), respectively. The piperidine ring adopts a chair conformation. In the molecule, intramolecular O—H⋯O hydrogen bonds form two S(6) ring motifs. In the crystal, molecules are linked via O—H⋯O and C—H⋯O hydrogen bonds, forming dimers.

Related literature

For studies on 1,4-dihydropyridine and piperidones reported by our group, see: Palakshi Reddy et al. (2011a ,b ,c ); Rathore et al. (2009 ); Rajesh et al. (2011 ). For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For ring conformations, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₉H₂₀F₆N₂O₈
M_r = 518.37
Monoclinic, C 2/c
a = 17.7353 (16) Å
b = 15.2025 (14) Å
c = 17.3003 (16) Å
β = 91.049 (2)°
V = 4663.7 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 296 K
0.21 × 0.21 × 0.14 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.970, T_max = 0.980
19801 measured reflections
5339 independent reflections
3229 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.125
S = 1.02
5339 reflections
376 parameters
104 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H1O7⋯O6	0.95 (3)	2.06 (3)	2.848 (2)	139 (3)
O8—H1O8⋯O4	0.94 (3)	2.09 (3)	2.839 (2)	136 (2)
O7—H1O7⋯O4ⁱ	0.95 (3)	2.28 (3)	2.882 (2)	121 (2)
O8—H1O8⋯O6ⁱ	0.94 (3)	2.26 (3)	2.877 (2)	123 (2)
C11—H11A⋯O7ⁱ	0.93	2.50	3.272 (2)	141
C11—H11A⋯O8ⁱ	0.93	2.44	3.222 (2)	142
Symmetry code: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811055346/rz2690sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811055346/rz2690Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811055346/rz2690Isup3.cml

checkCIF report

Comment top

In continuation of our earlier interest in 1,4-DHP's and piperidones (Palakshi Reddy et al., 2011a, b, c; Rathore et al., 2009; Rajesh et al., 2011), herein we report synthesis and crystal structure of diethyl 4-(3-nitrophenyl)-2,6-bis(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarboxylate.

In the molecular structure (Fig. 1), the ethoxy and ethyl groups are disordered over two sets of sites, with 0.212 (18):0.788 (18) and 0.746 (6):0.254 (6) occupancy ratios, respectively. The piperidine ring (N1/C1–C5) adopts a chair conformation with puckering parameters Q = 0.5933 (18) Å, θ = 166.58 (17)° and ϕ = 2.5 (8)° (Cremer & Pople, 1975). In addition, the mean plane through the piperidine ring and the benzene ring (C6–C10) are approximately perpedicular to each other with a dihedral angle of 89.59 (11)°. Intramolecular O7—H1O7···O6 and O8—H1O8···O4 hydrogen bonds (Table 1) stabilize the molecular structure and form two S(6) ring motifs (Bernstein et al., 1995). Bond lengths (Allen et al., 1987) and angles are within normal range.

The crystal packing is shown in Fig. 2. The molecules are linked via intermolecular O7—H1O7···O4, O8—H1O8···O6, C11—H11A···O7 and C11—H11A···O8 hydrogen bonds (Table 1) to form dimers.

Related literature top

For studies on 1,4-dihydropyridine and piperidones reported by our group, see: Palakshi Reddy et al. (2011a,b,c); Rathore et al. (2009); Rajesh et al. (2011). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformations, see: Cremer & Pople (1975).

Experimental top

A mixture of 3-nitrobenzaldehyde (1 mmol), ethyl 4,4,4-trifluoro-3-oxobutanoate (2 mmol) and ammonium acetate (1 mmol) were mixed along with 10 ml of ethanol and refluxed for about 2 h. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was cooled to room temperature and allowed to stand for 2 days. The solid product obtained was washed with ether and recrystallized from ethanol to give colourless crystals. M. p.: 395–397 K. Yield: 80%.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. All disordered components are shown. Intramolecular hydrogen bonds are shown as dashed lines
	Fig. 2. The crystal packing of the title compound viewed along the c axis. Dashed lines represent intermolecular hydrogen bonds. Only the major disordered components are shown.

Diethyl 2,6-dihydroxy-4-(3-nitrophenyl)- 2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate top

Crystal data top

C₁₉H₂₀F₆N₂O₈	F(000) = 2128
M_r = 518.37	D_x = 1.477 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4307 reflections
a = 17.7353 (16) Å	θ = 2.9–27.1°
b = 15.2025 (14) Å	µ = 0.14 mm⁻¹
c = 17.3003 (16) Å	T = 296 K
β = 91.049 (2)°	Block, colourless
V = 4663.7 (7) Å³	0.21 × 0.21 × 0.14 mm
Z = 8

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	5339 independent reflections
Radiation source: fine-focus sealed tube	3229 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −23→22
T_min = 0.970, T_max = 0.980	k = −19→19
19801 measured reflections	l = −22→22

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.125	w = 1/[σ²(F_o²) + (0.0493P)² + 2.0652P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
5339 reflections	Δρ_max = 0.21 e Å⁻³
376 parameters	Δρ_min = −0.19 e Å⁻³
104 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00084 (15)

Crystal data top

C₁₉H₂₀F₆N₂O₈	V = 4663.7 (7) Å³
M_r = 518.37	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 17.7353 (16) Å	µ = 0.14 mm⁻¹
b = 15.2025 (14) Å	T = 296 K
c = 17.3003 (16) Å	0.21 × 0.21 × 0.14 mm
β = 91.049 (2)°

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	5339 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3229 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.980	R_int = 0.028
19801 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	104 restraints
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.21 e Å⁻³
5339 reflections	Δρ_min = −0.19 e Å⁻³
376 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.

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	U_iso*/U_eq	Occ. (<1)
F1	0.36213 (8)	0.39434 (9)	0.23934 (8)	0.0892 (5)
F2	0.44369 (7)	0.30673 (10)	0.19217 (8)	0.0896 (5)
F3	0.37694 (9)	0.26642 (10)	0.28772 (7)	0.0906 (5)
F4	0.10958 (8)	0.36187 (10)	0.23426 (8)	0.0903 (5)
F5	0.04642 (7)	0.25576 (11)	0.18300 (8)	0.0940 (5)
F6	0.11954 (8)	0.23302 (10)	0.28156 (7)	0.0887 (5)
O1	0.26864 (19)	−0.15284 (15)	−0.12905 (13)	0.1564 (11)
O2	0.27330 (16)	−0.01793 (15)	−0.15351 (11)	0.1287 (9)
O3	0.4418 (19)	0.106 (3)	0.163 (2)	0.060 (4)	0.212 (18)
C13	0.4982 (16)	0.046 (2)	0.1072 (17)	0.103 (5)	0.212 (18)
H13A	0.4682	0.0137	0.0696	0.123*	0.212 (18)
H13B	0.5317	0.0851	0.0795	0.123*	0.212 (18)
C14	0.5328 (18)	−0.001 (2)	0.145 (2)	0.146 (8)	0.212 (18)
H14A	0.5785	−0.0162	0.1188	0.219*	0.212 (18)
H14B	0.5040	−0.0539	0.1532	0.219*	0.212 (18)
H14C	0.5449	0.0258	0.1934	0.219*	0.212 (18)
O3A	0.4362 (6)	0.0929 (8)	0.1583 (7)	0.085 (2)	0.788 (18)
C13A	0.5125 (4)	0.0683 (6)	0.1339 (4)	0.0949 (19)	0.788 (18)
H13C	0.5483	0.0687	0.1770	0.114*	0.788 (18)
H13D	0.5305	0.1067	0.0934	0.114*	0.788 (18)
C14A	0.4973 (5)	−0.0272 (5)	0.1033 (5)	0.127 (3)	0.788 (18)
H14D	0.5434	−0.0518	0.0846	0.191*	0.788 (18)
H14E	0.4604	−0.0253	0.0621	0.191*	0.788 (18)
H14F	0.4789	−0.0630	0.1446	0.191*	0.788 (18)
O4	0.41966 (8)	0.17953 (11)	0.05490 (9)	0.0736 (5)
O6	0.09483 (8)	0.14011 (10)	0.04494 (8)	0.0658 (4)
N1	0.24395 (8)	0.29412 (10)	0.19612 (8)	0.0462 (4)
H1N1	0.2380	0.3481	0.1947	0.069*
N2	0.27191 (15)	−0.07751 (16)	−0.10851 (13)	0.0909 (7)
O7	0.16066 (8)	0.30333 (9)	0.09062 (8)	0.0552 (4)
O8	0.32528 (8)	0.32280 (9)	0.09458 (8)	0.0551 (4)
C1	0.32495 (9)	0.17525 (12)	0.15245 (10)	0.0447 (4)
H1A	0.3228	0.1466	0.2031	0.054*
C2	0.25852 (9)	0.14162 (11)	0.10170 (9)	0.0413 (4)
H2A	0.2559	0.1780	0.0549	0.050*
C3	0.18628 (10)	0.15865 (12)	0.14797 (10)	0.0455 (4)
H3A	0.1924	0.1309	0.1988	0.055*
C4	0.17731 (10)	0.25802 (12)	0.16000 (10)	0.0471 (4)
C5	0.31612 (10)	0.27463 (12)	0.16372 (10)	0.0458 (4)
C6	0.26648 (11)	0.04661 (12)	0.07686 (10)	0.0480 (4)
C7	0.27170 (15)	−0.02213 (14)	0.12943 (13)	0.0756 (7)
H7A	0.2712	−0.0101	0.1821	0.091*
C8	0.27757 (19)	−0.10787 (16)	0.10466 (16)	0.0975 (10)
H8A	0.2809	−0.1532	0.1406	0.117*
C9	0.27849 (17)	−0.12666 (15)	0.02689 (16)	0.0892 (8)
H9A	0.2826	−0.1844	0.0097	0.107*
C10	0.27314 (13)	−0.05851 (14)	−0.02482 (12)	0.0649 (6)
C11	0.26732 (11)	0.02741 (13)	−0.00142 (11)	0.0525 (5)
H11A	0.2640	0.0724	−0.0378	0.063*
C12	0.39930 (11)	0.15197 (14)	0.11582 (12)	0.0543 (5)
C15	0.11874 (11)	0.11741 (14)	0.10727 (11)	0.0530 (5)
O5	0.09056 (9)	0.05249 (11)	0.14855 (9)	0.0774 (5)
C16	0.0290 (7)	0.0034 (8)	0.1123 (8)	0.088 (2)	0.746 (6)
H16A	0.0284	−0.0558	0.1331	0.105*	0.746 (6)
H16B	0.0375	−0.0007	0.0572	0.105*	0.746 (6)
C17	−0.0461 (2)	0.0461 (3)	0.1254 (3)	0.1125 (18)	0.746 (6)
H17A	−0.0856	0.0084	0.1062	0.169*	0.746 (6)
H17B	−0.0483	0.1014	0.0987	0.169*	0.746 (6)
H17C	−0.0524	0.0558	0.1798	0.169*	0.746 (6)
C16A	0.020 (2)	−0.006 (3)	0.121 (3)	0.110 (7)	0.254 (6)
H16C	−0.0045	−0.0335	0.1640	0.132*	0.254 (6)
H16D	−0.0160	0.0283	0.0908	0.132*	0.254 (6)
C17A	0.0617 (8)	−0.0715 (10)	0.0718 (8)	0.129 (6)	0.254 (6)
H17D	0.0261	−0.1119	0.0490	0.194*	0.254 (6)
H17E	0.0973	−0.1033	0.1035	0.194*	0.254 (6)
H17F	0.0879	−0.0411	0.0317	0.194*	0.254 (6)
C18	0.37467 (12)	0.31059 (15)	0.22174 (12)	0.0631 (6)
C19	0.11297 (13)	0.27698 (17)	0.21556 (12)	0.0662 (6)
H1O7	0.1249 (18)	0.270 (2)	0.0612 (18)	0.131 (12)*
H1O8	0.3669 (16)	0.3016 (18)	0.0676 (16)	0.107 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.1027 (11)	0.0731 (9)	0.0911 (10)	−0.0184 (8)	−0.0143 (8)	−0.0273 (8)
F2	0.0528 (8)	0.1192 (12)	0.0964 (10)	−0.0196 (7)	−0.0136 (7)	−0.0125 (9)
F3	0.1094 (11)	0.1064 (11)	0.0548 (7)	−0.0210 (9)	−0.0313 (7)	0.0068 (7)
F4	0.0893 (10)	0.0979 (11)	0.0846 (9)	0.0251 (8)	0.0223 (7)	−0.0234 (8)
F5	0.0472 (7)	0.1460 (14)	0.0895 (10)	0.0020 (8)	0.0177 (7)	−0.0190 (9)
F6	0.0921 (10)	0.1193 (12)	0.0559 (8)	0.0020 (8)	0.0331 (7)	0.0065 (8)
O1	0.278 (4)	0.0839 (15)	0.1069 (17)	0.0169 (18)	−0.0065 (19)	−0.0513 (13)
O2	0.235 (3)	0.0943 (16)	0.0572 (11)	0.0125 (16)	0.0104 (14)	−0.0131 (11)
O3	0.044 (7)	0.079 (8)	0.057 (7)	0.004 (6)	−0.012 (6)	−0.002 (6)
C13	0.079 (8)	0.125 (10)	0.103 (10)	0.054 (8)	−0.009 (8)	−0.031 (9)
C14	0.138 (15)	0.166 (17)	0.132 (16)	0.080 (13)	−0.004 (13)	−0.017 (14)
O3A	0.073 (4)	0.105 (5)	0.078 (3)	0.048 (3)	0.006 (3)	0.011 (3)
C13A	0.078 (3)	0.126 (5)	0.080 (3)	0.052 (3)	−0.007 (2)	−0.012 (3)
C14A	0.142 (6)	0.118 (5)	0.123 (5)	0.060 (4)	0.038 (4)	0.009 (4)
O4	0.0514 (9)	0.1103 (13)	0.0595 (9)	0.0113 (8)	0.0097 (7)	0.0095 (9)
O6	0.0560 (9)	0.0897 (11)	0.0515 (8)	−0.0178 (7)	−0.0057 (7)	0.0130 (8)
N1	0.0508 (9)	0.0483 (9)	0.0396 (8)	−0.0002 (7)	0.0042 (7)	−0.0060 (7)
N2	0.132 (2)	0.0692 (15)	0.0711 (14)	0.0120 (13)	0.0019 (13)	−0.0252 (12)
O7	0.0592 (8)	0.0592 (9)	0.0471 (7)	0.0066 (7)	−0.0009 (6)	0.0057 (6)
O8	0.0608 (9)	0.0571 (8)	0.0475 (7)	−0.0029 (7)	0.0057 (6)	0.0089 (6)
C1	0.0440 (10)	0.0502 (10)	0.0399 (9)	0.0018 (8)	−0.0015 (7)	0.0017 (8)
C2	0.0446 (10)	0.0419 (10)	0.0375 (9)	−0.0009 (8)	0.0014 (7)	0.0024 (7)
C3	0.0443 (10)	0.0533 (11)	0.0389 (9)	−0.0062 (8)	0.0027 (7)	0.0050 (8)
C4	0.0442 (10)	0.0583 (12)	0.0391 (9)	−0.0002 (8)	0.0062 (8)	−0.0001 (8)
C5	0.0466 (10)	0.0516 (11)	0.0392 (9)	−0.0041 (8)	0.0007 (8)	0.0000 (8)
C6	0.0562 (11)	0.0420 (10)	0.0456 (10)	−0.0019 (8)	0.0001 (8)	0.0043 (8)
C7	0.120 (2)	0.0524 (13)	0.0545 (12)	0.0009 (13)	−0.0073 (12)	0.0081 (11)
C8	0.167 (3)	0.0501 (14)	0.0751 (17)	0.0019 (16)	−0.0128 (18)	0.0135 (13)
C9	0.136 (2)	0.0401 (12)	0.0913 (19)	0.0018 (14)	−0.0111 (17)	−0.0053 (13)
C10	0.0848 (16)	0.0515 (12)	0.0583 (12)	0.0006 (11)	−0.0009 (11)	−0.0111 (10)
C11	0.0652 (13)	0.0460 (11)	0.0462 (10)	0.0023 (9)	0.0020 (9)	0.0001 (9)
C12	0.0459 (11)	0.0676 (13)	0.0494 (11)	0.0056 (9)	−0.0035 (9)	−0.0047 (10)
C15	0.0502 (11)	0.0625 (13)	0.0466 (11)	−0.0102 (9)	0.0058 (9)	0.0052 (9)
O5	0.0769 (11)	0.0878 (11)	0.0671 (9)	−0.0391 (9)	−0.0074 (8)	0.0215 (8)
C16	0.082 (4)	0.095 (4)	0.086 (4)	−0.056 (3)	−0.011 (3)	0.019 (3)
C17	0.075 (3)	0.134 (4)	0.129 (4)	−0.032 (3)	0.012 (2)	−0.007 (3)
C16A	0.101 (14)	0.120 (13)	0.109 (12)	−0.031 (12)	−0.013 (10)	0.037 (10)
C17A	0.136 (11)	0.134 (12)	0.116 (10)	−0.064 (9)	−0.050 (8)	0.012 (8)
C18	0.0622 (14)	0.0700 (15)	0.0568 (12)	−0.0126 (11)	−0.0081 (10)	−0.0028 (11)
C19	0.0577 (13)	0.0868 (17)	0.0546 (12)	0.0053 (12)	0.0142 (10)	−0.0058 (12)

Geometric parameters (Å, º) top

F1—C18	1.329 (3)	C1—C2	1.544 (2)
F2—C18	1.337 (2)	C1—H1A	0.9800
F3—C18	1.324 (2)	C2—C6	1.514 (2)
F4—C19	1.332 (3)	C2—C3	1.545 (2)
F5—C19	1.338 (3)	C2—H2A	0.9800
F6—C19	1.326 (3)	C3—C15	1.514 (3)
O1—N2	1.200 (3)	C3—C4	1.534 (3)
O2—N2	1.195 (3)	C3—H3A	0.9800
O3—C12	1.31 (4)	C4—C19	1.533 (3)
O3—C13	1.67 (5)	C5—C18	1.532 (3)
C13—C14	1.14 (5)	C6—C11	1.386 (2)
C13—H13A	0.9700	C6—C7	1.387 (3)
C13—H13B	0.9700	C7—C8	1.377 (3)
C14—H14A	0.9600	C7—H7A	0.9300
C14—H14B	0.9600	C8—C9	1.376 (3)
C14—H14C	0.9600	C8—H8A	0.9300
O3A—C12	1.326 (12)	C9—C10	1.371 (3)
O3A—C13A	1.473 (13)	C9—H9A	0.9300
C13A—C14A	1.567 (18)	C10—C11	1.372 (3)
C13A—H13C	0.9700	C11—H11A	0.9300
C13A—H13D	0.9700	C15—O5	1.322 (2)
C14A—H14D	0.9600	O5—C16	1.454 (11)
C14A—H14E	0.9600	O5—C16A	1.59 (4)
C14A—H14F	0.9600	C16—C17	1.503 (14)
O4—C12	1.196 (2)	C16—H16A	0.9700
O6—C15	1.202 (2)	C16—H16B	0.9700
N1—C4	1.436 (2)	C17—H17A	0.9600
N1—C5	1.438 (2)	C17—H17B	0.9600
N1—H1N1	0.8269	C17—H17C	0.9600
N2—C10	1.476 (3)	C16A—C17A	1.51 (4)
O7—C4	1.410 (2)	C16A—H16C	0.9700
O7—H1O7	0.95 (3)	C16A—H16D	0.9700
O8—C5	1.414 (2)	C17A—H17D	0.9600
O8—H1O8	0.94 (3)	C17A—H17E	0.9600
C1—C12	1.515 (3)	C17A—H17F	0.9600
C1—C5	1.532 (3)

C12—O3—C13	106 (3)	C11—C6—C7	118.70 (18)
C14—C13—O3	110 (3)	C11—C6—C2	118.75 (16)
C14—C13—H13A	111.0	C7—C6—C2	122.54 (17)
O3—C13—H13A	109.7	C8—C7—C6	120.9 (2)
C14—C13—H13B	109.7	C8—C7—H7A	119.5
O3—C13—H13B	109.7	C6—C7—H7A	119.5
H13A—C13—H13B	108.2	C9—C8—C7	120.2 (2)
C12—O3A—C13A	117.4 (10)	C9—C8—H8A	119.9
O3A—C13A—C14A	100.3 (9)	C7—C8—H8A	119.9
O3A—C13A—H13C	111.7	C10—C9—C8	118.6 (2)
C14A—C13A—H13C	111.7	C10—C9—H9A	120.7
O3A—C13A—H13D	111.7	C8—C9—H9A	120.7
C14A—C13A—H13D	111.7	C9—C10—C11	122.1 (2)
H13C—C13A—H13D	109.5	C9—C10—N2	119.5 (2)
C13A—C14A—H14D	109.5	C11—C10—N2	118.4 (2)
C13A—C14A—H14E	109.5	C10—C11—C6	119.42 (18)
H14D—C14A—H14E	109.5	C10—C11—H11A	120.3
C13A—C14A—H14F	109.5	C6—C11—H11A	120.3
H14D—C14A—H14F	109.5	O4—C12—O3	123.9 (19)
H14E—C14A—H14F	109.5	O4—C12—O3A	124.9 (6)
C4—N1—C5	118.89 (14)	O4—C12—C1	124.46 (18)
C4—N1—H1N1	105.3	O3—C12—C1	111.2 (19)
C5—N1—H1N1	107.8	O3A—C12—C1	110.6 (6)
O2—N2—O1	122.1 (2)	O6—C15—O5	124.63 (18)
O2—N2—C10	119.4 (2)	O6—C15—C3	124.15 (17)
O1—N2—C10	118.5 (3)	O5—C15—C3	111.21 (16)
C4—O7—H1O7	109.0 (19)	C15—O5—C16	116.0 (6)
C5—O8—H1O8	110.3 (17)	C15—O5—C16A	123.6 (17)
C12—C1—C5	112.05 (15)	O5—C16—C17	112.0 (8)
C12—C1—C2	110.23 (14)	O5—C16—H16A	109.2
C5—C1—C2	108.68 (14)	C17—C16—H16A	109.2
C12—C1—H1A	108.6	O5—C16—H16B	109.2
C5—C1—H1A	108.6	C17—C16—H16B	109.2
C2—C1—H1A	108.6	H16A—C16—H16B	107.9
C6—C2—C1	113.77 (14)	C17A—C16A—O5	99 (2)
C6—C2—C3	112.92 (14)	C17A—C16A—H16C	112.0
C1—C2—C3	106.34 (13)	O5—C16A—H16C	112.0
C6—C2—H2A	107.9	C17A—C16A—H16D	112.0
C1—C2—H2A	107.9	O5—C16A—H16D	112.0
C3—C2—H2A	107.9	H16C—C16A—H16D	109.7
C15—C3—C4	112.82 (16)	C16A—C17A—H17D	109.5
C15—C3—C2	110.25 (15)	C16A—C17A—H17E	109.5
C4—C3—C2	108.93 (14)	H17D—C17A—H17E	109.5
C15—C3—H3A	108.2	C16A—C17A—H17F	109.5
C4—C3—H3A	108.2	H17D—C17A—H17F	109.5
C2—C3—H3A	108.2	H17E—C17A—H17F	109.5
O7—C4—N1	109.97 (15)	F3—C18—F1	106.91 (18)
O7—C4—C19	107.16 (15)	F3—C18—F2	107.10 (19)
N1—C4—C19	105.75 (15)	F1—C18—F2	106.74 (18)
O7—C4—C3	112.72 (14)	F3—C18—C5	113.17 (17)
N1—C4—C3	110.43 (15)	F1—C18—C5	112.19 (18)
C19—C4—C3	110.53 (16)	F2—C18—C5	110.38 (17)
O8—C5—N1	109.87 (15)	F6—C19—F4	106.42 (18)
O8—C5—C1	112.92 (14)	F6—C19—F5	107.68 (19)
N1—C5—C1	110.29 (14)	F4—C19—F5	107.00 (19)
O8—C5—C18	106.40 (15)	F6—C19—C4	112.99 (18)
N1—C5—C18	105.58 (15)	F4—C19—C4	111.84 (19)
C1—C5—C18	111.45 (16)	F5—C19—C4	110.60 (17)

C12—O3—C13—C14	−174 (4)	C7—C6—C11—C10	0.1 (3)
C12—O3A—C13A—C14A	−108.6 (8)	C2—C6—C11—C10	−178.85 (18)
C12—C1—C2—C6	48.7 (2)	C13—O3—C12—O4	−33 (3)
C5—C1—C2—C6	171.81 (14)	C13—O3—C12—O3A	66 (13)
C12—C1—C2—C3	173.59 (15)	C13—O3—C12—C1	153.9 (18)
C5—C1—C2—C3	−63.26 (17)	C13A—O3A—C12—O4	8.6 (12)
C6—C2—C3—C15	−47.4 (2)	C13A—O3A—C12—O3	−80 (14)
C1—C2—C3—C15	−172.88 (15)	C13A—O3A—C12—C1	−175.2 (8)
C6—C2—C3—C4	−171.73 (14)	C5—C1—C12—O4	−57.3 (3)
C1—C2—C3—C4	62.81 (17)	C2—C1—C12—O4	63.8 (3)
C5—N1—C4—O7	−74.3 (2)	C5—C1—C12—O3	115.9 (16)
C5—N1—C4—C19	170.28 (16)	C2—C1—C12—O3	−123.0 (16)
C5—N1—C4—C3	50.7 (2)	C5—C1—C12—O3A	126.5 (5)
C15—C3—C4—O7	−54.4 (2)	C2—C1—C12—O3A	−112.3 (5)
C2—C3—C4—O7	68.37 (18)	C4—C3—C15—O6	57.1 (3)
C15—C3—C4—N1	−177.85 (14)	C2—C3—C15—O6	−65.0 (3)
C2—C3—C4—N1	−55.08 (18)	C4—C3—C15—O5	−124.01 (18)
C15—C3—C4—C19	65.5 (2)	C2—C3—C15—O5	113.95 (18)
C2—C3—C4—C19	−171.74 (15)	O6—C15—O5—C16	3.6 (7)
C4—N1—C5—O8	73.9 (2)	C3—C15—O5—C16	−175.3 (6)
C4—N1—C5—C1	−51.2 (2)	O6—C15—O5—C16A	0 (2)
C4—N1—C5—C18	−171.71 (16)	C3—C15—O5—C16A	−179 (2)
C12—C1—C5—O8	54.7 (2)	C15—O5—C16—C17	−85.9 (8)
C2—C1—C5—O8	−67.35 (18)	C16A—O5—C16—C17	74 (16)
C12—C1—C5—N1	178.06 (14)	C15—O5—C16A—C17A	84 (3)
C2—C1—C5—N1	56.01 (18)	C16—O5—C16A—C17A	63 (15)
C12—C1—C5—C18	−65.0 (2)	O8—C5—C18—F3	−174.73 (17)
C2—C1—C5—C18	172.94 (15)	N1—C5—C18—F3	68.5 (2)
C1—C2—C6—C11	−120.73 (19)	C1—C5—C18—F3	−51.2 (2)
C3—C2—C6—C11	117.93 (19)	O8—C5—C18—F1	64.2 (2)
C1—C2—C6—C7	60.4 (2)	N1—C5—C18—F1	−52.5 (2)
C3—C2—C6—C7	−61.0 (2)	C1—C5—C18—F1	−172.31 (16)
C11—C6—C7—C8	0.0 (4)	O8—C5—C18—F2	−54.7 (2)
C2—C6—C7—C8	178.9 (2)	N1—C5—C18—F2	−171.46 (17)
C6—C7—C8—C9	0.1 (5)	C1—C5—C18—F2	68.8 (2)
C7—C8—C9—C10	−0.3 (5)	O7—C4—C19—F6	175.74 (18)
C8—C9—C10—C11	0.3 (4)	N1—C4—C19—F6	−67.0 (2)
C8—C9—C10—N2	−178.3 (3)	C3—C4—C19—F6	52.6 (2)
O2—N2—C10—C9	−174.1 (3)	O7—C4—C19—F4	−64.2 (2)
O1—N2—C10—C9	6.8 (4)	N1—C4—C19—F4	53.1 (2)
O2—N2—C10—C11	7.2 (4)	C3—C4—C19—F4	172.61 (17)
O1—N2—C10—C11	−171.9 (3)	O7—C4—C19—F5	55.0 (2)
C9—C10—C11—C6	−0.2 (4)	N1—C4—C19—F5	172.24 (18)
N2—C10—C11—C6	178.4 (2)	C3—C4—C19—F5	−68.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H1O7···O6	0.95 (3)	2.06 (3)	2.848 (2)	139 (3)
O8—H1O8···O4	0.94 (3)	2.09 (3)	2.839 (2)	136 (2)
O7—H1O7···O4ⁱ	0.95 (3)	2.28 (3)	2.882 (2)	121 (2)
O8—H1O8···O6ⁱ	0.94 (3)	2.26 (3)	2.877 (2)	123 (2)
C11—H11A···O7ⁱ	0.93	2.50	3.272 (2)	141
C11—H11A···O8ⁱ	0.93	2.44	3.222 (2)	142

Symmetry code: (i) −x+1/2, −y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₀F₆N₂O₈
M_r	518.37
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	17.7353 (16), 15.2025 (14), 17.3003 (16)
β (°)	91.049 (2)
V (Å³)	4663.7 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.21 × 0.21 × 0.14

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.970, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	19801, 5339, 3229
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.125, 1.02
No. of reflections	5339
No. of parameters	376
No. of restraints	104
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.19

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H1O7···O6	0.95 (3)	2.06 (3)	2.848 (2)	139 (3)
O8—H1O8···O4	0.94 (3)	2.09 (3)	2.839 (2)	136 (2)
O7—H1O7···O4ⁱ	0.95 (3)	2.28 (3)	2.882 (2)	121 (2)
O8—H1O8···O6ⁱ	0.94 (3)	2.26 (3)	2.877 (2)	123 (2)
C11—H11A···O7ⁱ	0.9300	2.5000	3.272 (2)	141.00
C11—H11A···O8ⁱ	0.9300	2.4400	3.222 (2)	142.00

Symmetry code: (i) −x+1/2, −y+1/2, −z.

Footnotes

‡Visiting Professor, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). SA thanks the Malaysian Government and USM for the Academic Staff Training Scheme (ASTS) award. BPR, VV and SS are grateful to VIT University for providing facilities to carry out the research work.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
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Rajesh, K., Palakshi Reddy, B. & Vijayakumar, V. (2011). Ultrason. Sonochem. doi:10.1016/j.ultsonch.2011.10.018. Google Scholar
Rathore, R. S., Reddy, B. P., Vijayakumar, V., Ragavan, R. V. & Narasimhamurthy, T. (2009). Acta Cryst. B65, 375–381. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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Volume 68| Part 2| February 2012| Pages o400-o401

doi:10.1107/S1600536811055346

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di­ethyl 2,6-dihy­dr­oxy-4-(3-nitro­phen­yl)-2,6-bis­­(tri­fluoro­meth­yl)piperidine-3,5-di­carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

Diethyl 2,6-dihydroxy-4-(3-nitrophenyl)-2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate