3-Ethyl 5-methyl 2-hydr­oxy-6-methyl-4-(4-nitro­phen­yl)-2-trifluoro­methyl-1,2,3,4-tetra­hydro­pyridine-3,5-dicarboxyl­ate

Yu, C.-X.; Qian, P.-L.; Ping, J.-J.; Yao, C.-S.

doi:10.1107/S1600536808024835

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1737

doi:10.1107/S1600536808024835

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3-Ethyl 5-methyl 2-hydroxy-6-methyl-4-(4-nitrophenyl)-2-trifluoromethyl-1,2,3,4-tetrahydropyridine-3,5-dicarboxylate

Chen-Xia Yu,^a,^b Pei-Li Qian,^c Jia-Jing Ping ^c and Chang-Sheng Yao ^a,^b ^*

^aSchool of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116, People's Republic of China, ^bKey Laboratory of Biotechnology for Medicinal Plants, Xuzhou Normal University, Xuzhou 221116, People's Republic of China, and ^cKewen College, Xuzhou Normal University, Xuzhou 221116, People's Republic of China
^*Correspondence e-mail: chshengyaonk@mail.nankai.edu.cn

(Received 22 July 2008; accepted 2 August 2008; online 9 August 2008)

In the title compound, C₁₈H₁₉F₃N₂O₇, the tetrahydropyridine ring adopts a half-chair conformation. The nitro group is disordered over two sites with occupancies of 0.780 (15) and 0.220 (15). An intramolecular N—H⋯F hydrogen bond is observed in the molecular structure. The molecules are linked into a two-dimensional network parallel to (100) by O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For related literature, see: Achiwa & Kato (1999 ); Dubur et al. (1989 ); Hermann et al. (2003 ); Ulrich (2004 ).

Experimental

Crystal data

C₁₈H₁₉F₃N₂O₇
M_r = 432.35
Monoclinic, C 2/c
a = 28.678 (6) Å
b = 9.6678 (19) Å
c = 14.120 (3) Å
β = 95.72 (3)°
V = 3895.1 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 293 (2) K
0.16 × 0.16 × 0.04 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002 ) T_min = 0.979, T_max = 0.995
11673 measured reflections
3438 independent reflections
2572 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.150
S = 1.06
3438 reflections
284 parameters
14 restraints
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7⋯O5ⁱ	0.82	1.98	2.783 (3)	166
N2—H2⋯O3ⁱⁱ	0.86	2.20	3.030 (3)	163
N2—H2⋯F2	0.86	2.42	2.735 (2)	102
C5—H5⋯O2ⁱⁱⁱ	0.93	2.51	3.432 (4)	171
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ ; (ii) $[x, -y+1, z+{\script{1\over 2}}]$ ; (iii) $[-x, y, -z+{\script{3\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2002); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808024835/ci2642sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808024835/ci2642Isup2.hkl

checkCIF report

Comment top

1,4-Dihydropyridines are well known compounds as a consequence of their pharmacological profile as the most important calcium channel modulators (Achiwa & Kato, 1999). 4-Aryl-2,6-dimethyl-1,4-dihydropyridine -3,5-dicarboxylate derivatives are widely used for the treatment of cardiovascular diseases such as hypertension, angina pectoris and infarction (Dubur et al., 1989). In addition, compounds that contain fluorine have special bioactivity, for example, flumioxazin is a widely used herbicide (Hermann et al., 2003; Ulrich,2004). This led us to pay much attention to the synthesis and bioactivity of these fluoro-compounds. During the synthesis of trifluoromethylated 1,4-dihydropyridine derivatives, an intermediate, the title compound, was isolated. We report here the crystal structure of the title compound.

In the title molecule (Fig.1), the pyridine ring adopts a half-chair conformation, with atoms C10 and C11 deviating from the N2/C7/C8/C9 plane by 0.261 (4) Å and -0.544 (4)Å, respectively. The dihedral angle between the N2/C7/C8/C9 and C1-C6 planes is 72.30 (9)°. The N atom of the nitro group adopts a planar configuration in the major disorder component, while pyramidal configuration in the minor disorder component. An intramolecular N2—H2···F2 hydrogen bond is observed in the molecular structure.

The crystal packing is stabilized by O—H···O, N—H···O and C—H···O intermolecular hydrogen bonds (Table 1) which link the molecules into a two-dimensional network parallel to the (1 0 0) (Fig. 2).

Related literature top

For related literature, see: Achiwa & Kato (1999); Dubur et al. (1989); Hermann et al. (2003); Ulrich (2004).

Experimental top

The title compound was synthesized by the reaction of 4-nitrobenzaldehyde (1 mmol), methyl 3-amino-but-2-enoate (1 mmol) and ethyl 4,4,4-trifluoro-3-oxobutanoate (1 mmol) catalyzed by triethylbenzylaminium chloride (0.02 g) in water (10 ml) at 363 K. After cooling, the reaction mixture was washed with water and recrystallized from ethanol, to obtain single crystals suitable for X-ray diffraction.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2002); cell refinement: CrystalClear (Rigaku/MSC, 2002); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. Both disorder components are shown. The dashed line indicates a hydrogen bond.
	Fig. 2. The packing diagram of the title compound. Intermolecular hydrogen bonds are shown as dashed lines and H atoms not involved in hydrogen bonding have been omitted for clarity.

3-Ethyl 5-methyl 2-hydroxy-6-methyl-4-(4-nitrophenyl)-2-trifluoromethyl- 1,2,3,4-tetrahydropyridine-3,5-dicarboxylate top

Crystal data top

C₁₈H₁₉F₃N₂O₇	F(000) = 1792
M_r = 432.35	D_x = 1.475 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3562 reflections
a = 28.678 (6) Å	θ = 2.2–25.0°
b = 9.6678 (19) Å	µ = 0.13 mm⁻¹
c = 14.120 (3) Å	T = 293 K
β = 95.72 (3)°	Prism, colourless
V = 3895.1 (13) Å³	0.16 × 0.16 × 0.04 mm
Z = 8

Data collection top

Rigaku Saturn diffractometer	3438 independent reflections
Radiation source: rotating anode	2572 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.043
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.0°, θ_min = 2.2°
ω scans	h = −33→34
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002)	k = −11→11
T_min = 0.979, T_max = 0.995	l = −16→12
11673 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0873P)²] where P = (F_o² + 2F_c²)/3
3438 reflections	(Δ/σ)_max = 0.001
284 parameters	Δρ_max = 0.22 e Å⁻³
14 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₈H₁₉F₃N₂O₇	V = 3895.1 (13) Å³
M_r = 432.35	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 28.678 (6) Å	µ = 0.13 mm⁻¹
b = 9.6678 (19) Å	T = 293 K
c = 14.120 (3) Å	0.16 × 0.16 × 0.04 mm
β = 95.72 (3)°

Data collection top

Rigaku Saturn diffractometer	3438 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002)	2572 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.995	R_int = 0.043
11673 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	14 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.06	Δρ_max = 0.22 e Å⁻³
3438 reflections	Δρ_min = −0.21 e Å⁻³
284 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	0.08689 (6)	0.58977 (17)	0.93658 (13)	0.0775 (5)
F2	0.15032 (7)	0.70065 (15)	0.97856 (12)	0.0800 (6)
F3	0.12464 (6)	0.68534 (15)	0.83137 (11)	0.0725 (5)
O1	0.0452 (7)	−0.100 (2)	0.5112 (8)	0.086 (6)	0.220 (15)
O1'	0.06713 (19)	−0.1837 (7)	0.5322 (3)	0.090 (2)	0.780 (15)
O2	0.01478 (8)	−0.1793 (3)	0.63009 (19)	0.0972 (9)
O3	0.13847 (6)	0.44788 (18)	0.67834 (12)	0.0545 (5)
O4	0.06795 (6)	0.44145 (19)	0.73469 (12)	0.0594 (5)
O5	0.21673 (6)	0.00503 (18)	1.01751 (13)	0.0546 (5)
O6	0.21490 (6)	0.01870 (17)	0.85947 (12)	0.0512 (5)
O7	0.19972 (6)	0.52220 (18)	0.86560 (12)	0.0512 (5)
H7	0.2218	0.5189	0.9071	0.077*
N1	0.05038 (9)	−0.1349 (3)	0.6024 (2)	0.0738 (8)
N2	0.16656 (7)	0.42268 (18)	0.99703 (13)	0.0432 (5)
H2	0.1630	0.4725	1.0463	0.052*
C1	0.13495 (7)	0.1409 (2)	0.77500 (16)	0.0353 (5)
C2	0.14347 (8)	0.1173 (2)	0.68116 (16)	0.0424 (6)
H2A	0.1683	0.1621	0.6565	0.051*
C3	0.11549 (9)	0.0281 (2)	0.62409 (18)	0.0485 (6)
H3	0.1210	0.0132	0.5611	0.058*
C4	0.07957 (8)	−0.0378 (2)	0.66212 (18)	0.0469 (6)
C5	0.07026 (9)	−0.0190 (3)	0.75489 (19)	0.0502 (6)
H5	0.0458	−0.0659	0.7793	0.060*
C6	0.09829 (8)	0.0715 (2)	0.81067 (17)	0.0446 (6)
H6	0.0924	0.0860	0.8735	0.053*
C7	0.16340 (7)	0.2485 (2)	0.83367 (15)	0.0365 (5)
H7A	0.1902	0.2747	0.7996	0.044*
C8	0.18168 (7)	0.2018 (2)	0.93315 (15)	0.0354 (5)
C9	0.18004 (7)	0.2873 (2)	1.00940 (15)	0.0368 (5)
C10	0.15830 (8)	0.4834 (2)	0.90448 (17)	0.0427 (6)
C11	0.13175 (8)	0.3763 (2)	0.83985 (16)	0.0373 (5)
H11	0.1044	0.3473	0.8711	0.045*
C12	0.11414 (9)	0.4275 (2)	0.74130 (17)	0.0418 (6)
C13	0.04231 (12)	0.4735 (4)	0.6429 (2)	0.0755 (9)
H13A	0.0637	0.5090	0.5997	0.091*
H13B	0.0189	0.5439	0.6509	0.091*
C14	0.01957 (13)	0.3484 (4)	0.6032 (2)	0.0918 (11)
H14A	0.0430	0.2830	0.5884	0.138*
H14B	−0.0001	0.3712	0.5462	0.138*
H14C	0.0008	0.3086	0.6488	0.138*
C15	0.20522 (8)	0.0677 (2)	0.94376 (17)	0.0396 (5)
C16	0.23732 (10)	−0.1148 (3)	0.8569 (2)	0.0651 (8)
H16A	0.2607	−0.1231	0.9101	0.098*
H16B	0.2518	−0.1237	0.7987	0.098*
H16C	0.2143	−0.1864	0.8601	0.098*
C17	0.19319 (8)	0.2520 (2)	1.11186 (15)	0.0460 (6)
H17A	0.1907	0.3331	1.1502	0.069*
H17B	0.2249	0.2184	1.1198	0.069*
H17C	0.1725	0.1818	1.1313	0.069*
C18	0.12955 (10)	0.6156 (2)	0.91287 (19)	0.0543 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0761 (12)	0.0770 (11)	0.0819 (13)	0.0222 (9)	0.0199 (10)	−0.0030 (9)
F2	0.1242 (15)	0.0509 (9)	0.0612 (11)	0.0076 (9)	−0.0094 (10)	−0.0176 (8)
F3	0.1081 (13)	0.0524 (9)	0.0544 (10)	0.0161 (8)	−0.0046 (9)	0.0094 (7)
O1	0.085 (8)	0.118 (10)	0.055 (7)	−0.032 (7)	0.008 (5)	−0.026 (6)
O1'	0.093 (3)	0.111 (4)	0.069 (2)	−0.038 (3)	0.023 (2)	−0.052 (2)
O2	0.0728 (14)	0.1166 (18)	0.1066 (19)	−0.0437 (14)	0.0303 (14)	−0.0568 (16)
O3	0.0674 (11)	0.0622 (11)	0.0344 (10)	−0.0019 (8)	0.0074 (9)	0.0101 (8)
O4	0.0528 (11)	0.0799 (12)	0.0425 (11)	0.0022 (9)	−0.0094 (9)	0.0098 (9)
O5	0.0621 (11)	0.0555 (10)	0.0458 (11)	0.0078 (8)	0.0028 (9)	0.0114 (9)
O6	0.0595 (11)	0.0521 (10)	0.0420 (10)	0.0109 (8)	0.0042 (9)	−0.0055 (8)
O7	0.0536 (10)	0.0592 (10)	0.0403 (10)	−0.0162 (9)	0.0018 (8)	0.0045 (8)
N1	0.0681 (16)	0.0885 (18)	0.0668 (18)	−0.0311 (14)	0.0167 (14)	−0.0349 (15)
N2	0.0620 (13)	0.0418 (10)	0.0254 (10)	0.0000 (9)	0.0027 (9)	−0.0041 (8)
C1	0.0372 (12)	0.0379 (11)	0.0307 (12)	0.0012 (9)	0.0025 (10)	−0.0011 (9)
C2	0.0468 (13)	0.0470 (13)	0.0348 (13)	−0.0064 (11)	0.0109 (11)	−0.0042 (11)
C3	0.0543 (15)	0.0555 (14)	0.0368 (14)	−0.0044 (12)	0.0099 (12)	−0.0133 (11)
C4	0.0476 (14)	0.0504 (13)	0.0425 (14)	−0.0070 (11)	0.0032 (12)	−0.0148 (11)
C5	0.0478 (14)	0.0553 (14)	0.0487 (15)	−0.0135 (12)	0.0103 (12)	−0.0045 (12)
C6	0.0506 (14)	0.0524 (13)	0.0318 (13)	−0.0075 (11)	0.0097 (11)	−0.0045 (11)
C7	0.0392 (12)	0.0414 (11)	0.0291 (11)	−0.0038 (9)	0.0047 (10)	0.0004 (10)
C8	0.0356 (11)	0.0421 (11)	0.0286 (12)	−0.0036 (9)	0.0028 (9)	0.0022 (9)
C9	0.0360 (11)	0.0447 (12)	0.0294 (12)	−0.0058 (10)	0.0008 (9)	0.0023 (10)
C10	0.0536 (14)	0.0420 (12)	0.0320 (13)	−0.0026 (10)	0.0022 (11)	0.0012 (10)
C11	0.0420 (12)	0.0408 (11)	0.0291 (12)	−0.0032 (10)	0.0030 (10)	0.0001 (9)
C12	0.0521 (14)	0.0390 (12)	0.0338 (13)	−0.0027 (10)	0.0016 (12)	0.0007 (10)
C13	0.076 (2)	0.095 (2)	0.0499 (18)	0.0053 (18)	−0.0195 (16)	0.0128 (17)
C14	0.091 (2)	0.114 (3)	0.065 (2)	−0.019 (2)	−0.0149 (19)	−0.008 (2)
C15	0.0373 (12)	0.0449 (12)	0.0363 (13)	−0.0063 (10)	0.0015 (10)	−0.0001 (11)
C16	0.0681 (18)	0.0536 (15)	0.072 (2)	0.0125 (13)	0.0009 (16)	−0.0161 (14)
C17	0.0544 (14)	0.0520 (13)	0.0309 (13)	−0.0051 (11)	0.0000 (11)	0.0020 (11)
C18	0.0761 (19)	0.0455 (14)	0.0403 (15)	0.0047 (13)	0.0008 (14)	−0.0029 (12)

Geometric parameters (Å, º) top

F1—C18	1.324 (3)	C5—C6	1.380 (3)
F2—C18	1.335 (3)	C5—H5	0.93
F3—C18	1.329 (3)	C6—H6	0.93
O1—N1	1.325 (13)	C7—C8	1.518 (3)
O1'—N1	1.237 (4)	C7—C11	1.541 (3)
O2—N1	1.208 (3)	C7—H7A	0.98
O3—C12	1.200 (3)	C8—C9	1.362 (3)
O4—C12	1.326 (3)	C8—C15	1.462 (3)
O4—C13	1.458 (3)	C9—C17	1.498 (3)
O5—C15	1.221 (3)	C10—C18	1.532 (3)
O6—C15	1.336 (3)	C10—C11	1.532 (3)
O6—C16	1.444 (3)	C11—C12	1.515 (3)
O7—C10	1.408 (3)	C11—H11	0.98
O7—H7	0.82	C13—C14	1.459 (5)
N1—C4	1.467 (3)	C13—H13A	0.97
N2—C9	1.371 (3)	C13—H13B	0.97
N2—C10	1.431 (3)	C14—H14A	0.96
N2—H2	0.86	C14—H14B	0.96
C1—C6	1.384 (3)	C14—H14C	0.96
C1—C2	1.390 (3)	C16—H16A	0.96
C1—C7	1.516 (3)	C16—H16B	0.96
C2—C3	1.381 (3)	C16—H16C	0.96
C2—H2A	0.93	C17—H17A	0.96
C3—C4	1.366 (3)	C17—H17B	0.96
C3—H3	0.93	C17—H17C	0.96
C4—C5	1.375 (4)

C12—O4—C13	119.7 (2)	N2—C10—C11	107.09 (18)
C15—O6—C16	118.2 (2)	C18—C10—C11	111.8 (2)
C10—O7—H7	109.5	C12—C11—C10	115.27 (18)
O2—N1—O1'	122.1 (3)	C12—C11—C7	110.74 (18)
O1'—N1—C4	117.4 (2)	C10—C11—C7	108.39 (18)
O2—N1—C4	119.6 (2)	C12—C11—H11	107.4
O2—N1—O1	112.9 (7)	C10—C11—H11	107.4
O1—N1—C4	113.5 (6)	C7—C11—H11	107.4
C9—N2—C10	121.81 (19)	O3—C12—O4	125.6 (2)
C9—N2—H2	119.1	O3—C12—C11	124.7 (2)
C10—N2—H2	119.1	O4—C12—C11	109.7 (2)
C6—C1—C2	118.6 (2)	O4—C13—C14	109.4 (3)
C6—C1—C7	121.39 (19)	O4—C13—H13A	109.8
C2—C1—C7	119.82 (19)	C14—C13—H13A	109.8
C3—C2—C1	120.8 (2)	O4—C13—H13B	109.8
C3—C2—H2A	119.6	C14—C13—H13B	109.8
C1—C2—H2A	119.6	H13A—C13—H13B	108.2
C4—C3—C2	118.6 (2)	C13—C14—H14A	109.5
C4—C3—H3	120.7	C13—C14—H14B	109.5
C2—C3—H3	120.7	H14A—C14—H14B	109.5
C3—C4—C5	122.6 (2)	C13—C14—H14C	109.5
C3—C4—N1	118.8 (2)	H14A—C14—H14C	109.5
C5—C4—N1	118.6 (2)	H14B—C14—H14C	109.5
C4—C5—C6	118.0 (2)	O5—C15—O6	121.4 (2)
C4—C5—H5	121.0	O5—C15—C8	127.6 (2)
C6—C5—H5	121.0	O6—C15—C8	111.0 (2)
C5—C6—C1	121.3 (2)	O6—C16—H16A	109.5
C5—C6—H6	119.3	O6—C16—H16B	109.5
C1—C6—H6	119.3	H16A—C16—H16B	109.5
C1—C7—C8	114.77 (17)	O6—C16—H16C	109.5
C1—C7—C11	107.06 (17)	H16A—C16—H16C	109.5
C8—C7—C11	109.70 (17)	H16B—C16—H16C	109.5
C1—C7—H7A	108.4	C9—C17—H17A	109.5
C8—C7—H7A	108.4	C9—C17—H17B	109.5
C11—C7—H7A	108.4	H17A—C17—H17B	109.5
C9—C8—C15	120.6 (2)	C9—C17—H17C	109.5
C9—C8—C7	121.00 (19)	H17A—C17—H17C	109.5
C15—C8—C7	118.15 (19)	H17B—C17—H17C	109.5
C8—C9—N2	120.7 (2)	F1—C18—F3	107.1 (2)
C8—C9—C17	126.9 (2)	F1—C18—F2	107.5 (2)
N2—C9—C17	112.41 (19)	F3—C18—F2	106.9 (2)
O7—C10—N2	113.3 (2)	F1—C18—C10	112.3 (2)
O7—C10—C18	106.83 (19)	F3—C18—C10	111.6 (2)
N2—C10—C18	108.25 (19)	F2—C18—C10	111.2 (2)
O7—C10—C11	109.64 (18)

C6—C1—C2—C3	1.0 (3)	O7—C10—C11—C12	−64.1 (3)
C7—C1—C2—C3	−174.7 (2)	N2—C10—C11—C12	172.51 (19)
C1—C2—C3—C4	−0.7 (4)	C18—C10—C11—C12	54.1 (3)
C2—C3—C4—C5	−0.2 (4)	O7—C10—C11—C7	60.6 (2)
C2—C3—C4—N1	−178.7 (2)	N2—C10—C11—C7	−62.8 (2)
O2—N1—C4—C3	−169.9 (3)	C18—C10—C11—C7	178.84 (19)
O1'—N1—C4—C3	20.9 (6)	C1—C7—C11—C12	−56.5 (2)
O1—N1—C4—C3	−32.6 (13)	C8—C7—C11—C12	178.39 (18)
O2—N1—C4—C5	11.5 (4)	C1—C7—C11—C10	176.15 (17)
O1'—N1—C4—C5	−157.7 (5)	C8—C7—C11—C10	51.0 (2)
O1—N1—C4—C5	148.8 (12)	C13—O4—C12—O3	5.3 (4)
C3—C4—C5—C6	0.7 (4)	C13—O4—C12—C11	−172.6 (2)
N1—C4—C5—C6	179.3 (2)	C10—C11—C12—O3	74.1 (3)
C4—C5—C6—C1	−0.4 (4)	C7—C11—C12—O3	−49.4 (3)
C2—C1—C6—C5	−0.4 (3)	C10—C11—C12—O4	−108.0 (2)
C7—C1—C6—C5	175.2 (2)	C7—C11—C12—O4	128.5 (2)
C6—C1—C7—C8	50.4 (3)	C12—O4—C13—C14	102.9 (3)
C2—C1—C7—C8	−134.0 (2)	C16—O6—C15—O5	3.2 (3)
C6—C1—C7—C11	−71.6 (3)	C16—O6—C15—C8	−178.7 (2)
C2—C1—C7—C11	104.0 (2)	C9—C8—C15—O5	16.0 (3)
C1—C7—C8—C9	−137.4 (2)	C7—C8—C15—O5	−169.7 (2)
C11—C7—C8—C9	−16.9 (3)	C9—C8—C15—O6	−161.96 (19)
C1—C7—C8—C15	48.4 (2)	C7—C8—C15—O6	12.3 (3)
C11—C7—C8—C15	168.92 (18)	O7—C10—C18—F1	171.4 (2)
C15—C8—C9—N2	166.91 (19)	N2—C10—C18—F1	−66.2 (3)
C7—C8—C9—N2	−7.1 (3)	C11—C10—C18—F1	51.5 (3)
C15—C8—C9—C17	−11.1 (3)	O7—C10—C18—F3	51.2 (3)
C7—C8—C9—C17	174.88 (19)	N2—C10—C18—F3	173.5 (2)
C10—N2—C9—C8	−6.4 (3)	C11—C10—C18—F3	−68.8 (3)
C10—N2—C9—C17	171.9 (2)	O7—C10—C18—F2	−68.1 (3)
C9—N2—C10—O7	−79.4 (3)	N2—C10—C18—F2	54.3 (3)
C9—N2—C10—C18	162.2 (2)	C11—C10—C18—F2	172.0 (2)
C9—N2—C10—C11	41.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7···O5ⁱ	0.82	1.98	2.783 (3)	166
N2—H2···O3ⁱⁱ	0.86	2.20	3.030 (3)	163
N2—H2···F2	0.86	2.42	2.735 (2)	102
C5—H5···O2ⁱⁱⁱ	0.93	2.51	3.432 (4)	171

Symmetry codes: (i) −x+1/2, −y+1/2, −z+2; (ii) x, −y+1, z+1/2; (iii) −x, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₉F₃N₂O₇
M_r	432.35
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	28.678 (6), 9.6678 (19), 14.120 (3)
β (°)	95.72 (3)
V (Å³)	3895.1 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.16 × 0.16 × 0.04

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2002)
T_min, T_max	0.979, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	11673, 3438, 2572
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.150, 1.06
No. of reflections	3438
No. of parameters	284
No. of restraints	14
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.21

Computer programs: CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7···O5ⁱ	0.82	1.98	2.783 (3)	166
N2—H2···O3ⁱⁱ	0.86	2.20	3.030 (3)	163
N2—H2···F2	0.86	2.42	2.735 (2)	102
C5—H5···O2ⁱⁱⁱ	0.93	2.51	3.432 (4)	171

Symmetry codes: (i) −x+1/2, −y+1/2, −z+2; (ii) x, −y+1, z+1/2; (iii) −x, y, −z+3/2.

Acknowledgements

The authors thank the Natural Science Foundation of Xuzhou Normal University (grant No. 06XLB07) and the Natural Science Foundation of Xuzhou City (grant No. XJ07065) for financial support.

References

Achiwa, K. & Kato, T. (1999). Curr. Org. Chem. 3, 77–106. CAS Google Scholar
Dubur, G. J., Veveris, M. M., Weinheimer, G., Bisenieks, E. A., Makarova, N. R., Kimenis, A. A., Uldrikis, J. R., Lukevics, E. J., Dooley, D. & Osswald, H. (1989). Arzneim. Forsch. 39, 1185–1189. CAS Google Scholar
Hermann, B., Erwin, H. & Hansjorg, K. (2003). US patent 2 003 176 284. Google Scholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ulrich, H. (2004). US patent 2 004 033 897. Google Scholar

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Volume 64| Part 9| September 2008| Page o1737

doi:10.1107/S1600536808024835

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

3-Ethyl 5-methyl 2-hydr­­oxy-6-methyl-4-(4-nitro­phen­yl)-2-tri­fluoro­methyl-1,2,3,4-tetra­hydro­pyridine-3,5-di­carboxyl­ate

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3-Ethyl 5-methyl 2-hydroxy-6-methyl-4-(4-nitrophenyl)-2-trifluoromethyl-1,2,3,4-tetrahydropyridine-3,5-dicarboxylate