(S)-1-[3,5-Bis­(trifluoro­meth­yl)phen­yl]-N-methylethyl­amine–(R)-2-hydroxy­butane­dioic acid (1/1)

Zhu, H.-B.; Ji, J.-F.; Wang, H.

doi:10.1107/S1600536808043201

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o197

doi:10.1107/S1600536808043201

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(S)-1-[3,5-Bis(trifluoromethyl)phenyl]-N-methylethylamine–(R)-2-hydroxybutanedioic acid (1/1)

Hai-Bin Zhu,^a ^* Jun-Feng Ji ^a and Hai Wang ^a

^aSchool of Chemistry and Chemical Engineering, Southeast University, Nanjing, People's Republic of China
^*Correspondence e-mail: zhuhaibin@seu.edu.cn

(Received 8 December 2008; accepted 18 December 2008; online 24 December 2008)

In the title compound, C₁₁H₁₁F₆N·C₄H₆O₅, a key intermediate in the synthesis of the NK1 receptor antagonist of casopitant, the F atoms of the trifluoromethyl groups are disordered over two sites with equal occupancies. In the crystal, the components are linked by bifurcated N—H⋯(O,O) hydrogen bonds.

Related literature

The title compound is a key intermediate for the synthesis of casopitant, which is an NK1 receptor antagonist (Humphrey, 2003 ) for the treatment of chemotheraphy-induced nausea and vomiting (CINV) (Lohr, 2008 ).

Experimental

Crystal data

C₁₁H₁₁F₆N·C₄H₆O₅
M_r = 405.30
Monoclinic, P 2₁
a = 6.6770 (13) Å
b = 8.4510 (17) Å
c = 16.366 (3) Å
β = 100.05 (3)°
V = 909.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 298 (2) K
0.30 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.957, T_max = 0.985
1915 measured reflections
1757 independent reflections
1067 reflections with I > 2σ(I)
R_int = 0.058
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.154
S = 1.00
1757 reflections
220 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯O4ⁱ	0.86	2.37	2.914 (7)	122
N—H0A⋯O3ⁱⁱ	0.86	2.20	2.887 (7)	137
Symmetry codes: (i) x-1, y, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

Data collection: CAD-4 Software (Enraf–Nonius,1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808043201/at2692sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808043201/at2692Isup2.hkl

checkCIF report

Comment top

The title compound, C₁₁H₁₁F₆N.C₄H₆O₅, is a key intermediate for the synthesis of casopitant, which is an NK1 receptor antagonist (Humphrey, 2003) for the treatment of chemotheraphy-induced nausea and vomiting (CINV) (Lohr, 2008).

The molecular structure of the title compound is shown in Fig.1. The F atoms of the trifluoromethyl group are disordered over two sites in a 0.50:0.50 ratio. N—H···O hydrogen bonding interactions occur between (S)-1-(3, 5-bis(trifluoromethyl)-phenyl)ethylamine N-monomethyl and (R)-2-hydroxybutanedioic acid (Table 1).

Related literature top

For the NK1 receptor antagonist, see: Humphrey (2003).

Experimental top

To a solution of 3, 5-bis(trifluoromethyl)-phenyl)ethylamine N-monomethyl (2.71 g, 10 mmol) in EtOAc (25 ml), (R)-2-hydroxybutanedioic acid (1.34,10 mmol) was added portionwise. The suspension was stirred for 2h at 298 K, then for 3 h at 273 K. The suspension was filtered and the cake was washed with EtOAc (20 ml). The solid was dried under vacucum obtaining the crude title compound (1.48 g). Single crystal of the title compound suitable for X-ray diffraction was obtained by slow evaporation of the EtOAc solution of the title compound.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius,1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, drawn with 30% probability ellipsoids.

(S)-1-[3,5-Bis(trifluoromethyl)phenyl]-N-methylethylamine– (R)-2-hydroxybutanedioic acid (1/1) top

Crystal data top

C₁₁H₁₁F₆N·C₄H₆O₅	F(000) = 416
M_r = 405.30	D_x = 1.480 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 6.6770 (13) Å	θ = 9–12°
b = 8.4510 (17) Å	µ = 0.15 mm⁻¹
c = 16.366 (3) Å	T = 298 K
β = 100.05 (3)°	Needle, colourless
V = 909.3 (3) Å³	0.30 × 0.10 × 0.10 mm
Z = 2

Data collection top

Enraf–Nonius CAD-4 diffractometer	1067 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.058
Graphite monochromator	θ_max = 25.3°, θ_min = 1.3°
ω/2θ scans	h = 0→7
Absorption correction: ψ scan (North et al., 1968)	k = 0→10
T_min = 0.957, T_max = 0.985	l = −19→19
1915 measured reflections	3 standard reflections every 200 reflections
1757 independent reflections	intensity decay: 1%

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.060P)² + 0.3P] where P = (F_o² + 2F_c²)/3
1757 reflections	(Δ/σ)_max < 0.001
220 parameters	Δρ_max = 0.18 e Å⁻³
2 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₁H₁₁F₆N·C₄H₆O₅	V = 909.3 (3) Å³
M_r = 405.30	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 6.6770 (13) Å	µ = 0.15 mm⁻¹
b = 8.4510 (17) Å	T = 298 K
c = 16.366 (3) Å	0.30 × 0.10 × 0.10 mm
β = 100.05 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1067 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.058
T_min = 0.957, T_max = 0.985	3 standard reflections every 200 reflections
1915 measured reflections	intensity decay: 1%
1757 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	2 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.00	Δρ_max = 0.18 e Å⁻³
1757 reflections	Δρ_min = −0.27 e Å⁻³
220 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	0.9058 (17)	0.4852 (16)	0.9973 (8)	0.112	0.50
F3	0.9270 (13)	0.6270 (13)	0.8772 (6)	0.083	0.50
F2	1.0892 (15)	0.4013 (14)	0.9084 (6)	0.101	0.50
F1'	0.7985 (16)	0.6070 (16)	0.9651 (7)	0.111	0.50
F2'	1.000 (2)	0.4376 (16)	0.9758 (7)	0.111	0.50
F3'	0.9991 (17)	0.5461 (16)	0.8769 (7)	0.115	0.50
F4	0.5055 (13)	−0.0158 (14)	0.9651 (7)	0.085	0.50
F5	0.3781 (15)	−0.0926 (12)	0.8429 (6)	0.080	0.50
F6	0.6975 (13)	−0.0918 (12)	0.8664 (6)	0.078	0.50
F4'	0.5831 (15)	−0.0443 (15)	0.9665 (8)	0.097	0.50
F5'	0.3083 (15)	−0.0556 (14)	0.8707 (6)	0.095	0.50
F6'	0.6174 (16)	−0.1374 (14)	0.8609 (7)	0.093	0.50
N	0.3387 (7)	0.3503 (6)	0.6045 (3)	0.0464 (12)
H0A	0.2534	0.2888	0.5744	0.056*
C1	0.8859 (12)	0.4933 (11)	0.9164 (5)	0.081
C2	0.5244 (14)	−0.0104 (14)	0.8816 (5)	0.094 (3)
C3	0.5326 (11)	0.1454 (10)	0.8548 (4)	0.063 (2)
C4	0.4157 (10)	0.2037 (8)	0.7869 (4)	0.0543 (17)
H4A	0.3136	0.1408	0.7574	0.065*
C5	0.4445 (9)	0.3611 (9)	0.7587 (4)	0.0527 (16)
C6	0.5931 (11)	0.4465 (10)	0.8000 (4)	0.072 (2)
H6A	0.6137	0.5488	0.7821	0.087*
C7	0.7249 (13)	0.3856 (12)	0.8723 (5)	0.080 (2)
C8	0.6962 (12)	0.2426 (12)	0.8978 (5)	0.079 (3)
H8A	0.7817	0.2026	0.9441	0.095*
C9	0.3017 (8)	0.4239 (8)	0.6855 (3)	0.0482 (15)
H9A	0.3274	0.5377	0.6823	0.058*
C10	0.0783 (9)	0.4033 (9)	0.6903 (4)	0.0646 (19)
H10A	0.0507	0.4508	0.7405	0.097*
H10B	0.0461	0.2926	0.6902	0.097*
H10C	−0.0033	0.4535	0.6433	0.097*
C11	0.5373 (9)	0.3961 (9)	0.5832 (4)	0.0606 (18)
H11A	0.5542	0.3455	0.5323	0.091*
H11B	0.6447	0.3636	0.6269	0.091*
H11C	0.5419	0.5088	0.5766	0.091*
O1	0.6777 (8)	0.0742 (7)	0.6474 (4)	0.0869 (18)
O2	0.5220 (7)	−0.1471 (5)	0.6689 (3)	0.0652 (13)
H2A	0.4226	−0.0912	0.6526	0.098*
O3	0.8263 (6)	−0.2740 (5)	0.5576 (3)	0.0579 (12)
H3A	0.8825	−0.3437	0.5351	0.087*
O4	1.1965 (6)	0.0264 (5)	0.6157 (3)	0.0540 (11)
O5	0.9516 (7)	0.0076 (6)	0.5086 (3)	0.0678 (15)
H5A	1.0184	0.0743	0.4888	0.102*
C12	0.6858 (11)	−0.0671 (9)	0.6676 (4)	0.0551 (17)
C13	0.8797 (9)	−0.1508 (8)	0.6891 (4)	0.0522 (15)
H13A	0.8587	−0.2481	0.7179	0.063*
H13B	0.9744	−0.0857	0.7265	0.063*
C14	0.9715 (8)	−0.1898 (7)	0.6122 (3)	0.0428 (14)
H14A	1.0894	−0.2588	0.6292	0.051*
C15	1.0461 (9)	−0.0360 (7)	0.5766 (4)	0.0464 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.112	0.112	0.112	0.000	0.020	0.000
F3	0.083	0.083	0.083	0.000	0.015	0.000
F2	0.101	0.101	0.101	0.000	0.018	0.000
F1'	0.111	0.111	0.111	0.000	0.019	0.000
F2'	0.111	0.111	0.111	0.000	0.019	0.000
F3'	0.115	0.115	0.115	0.000	0.020	0.000
F4	0.085	0.085	0.085	0.000	0.015	0.000
F5	0.080	0.080	0.080	0.000	0.014	0.000
F6	0.078	0.078	0.078	0.000	0.014	0.000
F4'	0.097	0.097	0.097	0.000	0.017	0.000
F5'	0.095	0.095	0.095	0.000	0.017	0.000
F6'	0.093	0.093	0.093	0.000	0.016	0.000
N	0.050 (3)	0.044 (3)	0.047 (3)	−0.015 (3)	0.010 (2)	−0.004 (3)
C1	0.072	0.100	0.067	−0.033	−0.003	0.033
C2	0.097 (7)	0.114 (8)	0.069 (6)	0.014 (7)	0.012 (5)	0.000 (6)
C3	0.063 (4)	0.065 (5)	0.059 (4)	0.016 (4)	0.005 (4)	0.000 (4)
C4	0.055 (4)	0.058 (4)	0.048 (3)	−0.002 (4)	0.002 (3)	0.002 (3)
C5	0.053 (4)	0.065 (5)	0.042 (3)	−0.004 (4)	0.013 (3)	−0.002 (3)
C6	0.075 (5)	0.084 (6)	0.055 (4)	−0.014 (5)	0.003 (4)	−0.012 (4)
C7	0.068 (5)	0.076 (6)	0.089 (6)	−0.003 (5)	−0.006 (4)	0.001 (5)
C8	0.068 (5)	0.102 (7)	0.061 (5)	0.000 (5)	−0.007 (4)	−0.014 (5)
C9	0.053 (3)	0.045 (3)	0.045 (3)	0.009 (3)	0.003 (3)	0.007 (3)
C10	0.054 (4)	0.069 (5)	0.073 (4)	0.005 (4)	0.017 (3)	0.014 (4)
C11	0.047 (3)	0.062 (4)	0.072 (4)	−0.015 (3)	0.010 (3)	0.003 (4)
O1	0.081 (4)	0.067 (4)	0.120 (5)	0.011 (3)	0.037 (3)	0.010 (4)
O2	0.068 (3)	0.053 (3)	0.074 (3)	−0.002 (3)	0.009 (2)	0.002 (3)
O3	0.059 (3)	0.043 (2)	0.074 (3)	−0.012 (2)	0.018 (2)	−0.011 (2)
O4	0.046 (2)	0.053 (3)	0.062 (3)	−0.011 (2)	0.009 (2)	−0.002 (2)
O5	0.082 (3)	0.066 (3)	0.052 (2)	−0.022 (3)	0.003 (2)	0.015 (3)
C12	0.062 (4)	0.061 (4)	0.046 (4)	−0.003 (4)	0.022 (3)	−0.005 (3)
C13	0.060 (4)	0.051 (4)	0.048 (3)	0.005 (4)	0.016 (3)	0.003 (3)
C14	0.041 (3)	0.048 (4)	0.042 (3)	0.007 (3)	0.014 (3)	0.006 (3)
C15	0.046 (3)	0.036 (3)	0.061 (4)	0.005 (3)	0.020 (3)	−0.004 (3)

Geometric parameters (Å, º) top

F1—C1	1.309 (14)	C7—C8	1.304 (13)
F3—C1	1.352 (13)	C8—H8A	0.9300
F2—C1	1.589 (14)	C9—C10	1.517 (8)
F1'—C1	1.436 (13)	C9—H9A	0.9800
F2'—C1	1.219 (13)	C10—H10A	0.9600
F3'—C1	1.167 (12)	C10—H10B	0.9600
F4—C2	1.395 (13)	C10—H10C	0.9600
F5—C2	1.274 (12)	C11—H11A	0.9600
F6—C2	1.404 (11)	C11—H11B	0.9600
F4'—C2	1.405 (14)	C11—H11C	0.9600
F5'—C2	1.474 (13)	O1—C12	1.237 (9)
F6'—C2	1.313 (15)	O2—C12	1.290 (8)
N—C11	1.480 (7)	O2—H2A	0.8200
N—C9	1.523 (7)	O3—C14	1.394 (7)
N—H0A	0.8600	O3—H3A	0.8200
C1—C7	1.495 (11)	O4—C15	1.213 (7)
C2—C3	1.392 (13)	O5—C15	1.236 (7)
C3—C4	1.336 (9)	O5—H5A	0.8200
C3—C8	1.447 (11)	C12—C13	1.463 (9)
C4—C5	1.432 (10)	C13—C14	1.530 (8)
C4—H4A	0.9300	C13—H13A	0.9700
C5—C6	1.315 (9)	C13—H13B	0.9700
C5—C9	1.492 (8)	C14—C15	1.543 (8)
C6—C7	1.441 (10)	C14—H14A	0.9800
C6—H6A	0.9300

C11—N—C9	112.7 (5)	C5—C6—C7	121.6 (8)
C11—N—H0A	123.6	C5—C6—H6A	119.2
C9—N—H0A	123.6	C7—C6—H6A	119.2
F3'—C1—F2'	102.5 (11)	C8—C7—C6	119.4 (8)
F3'—C1—F1	128.3 (11)	C8—C7—C1	122.9 (8)
F2'—C1—F3	123.5 (10)	C6—C7—C1	117.6 (8)
F1—C1—F3	122.1 (10)	C7—C8—C3	120.8 (8)
F3'—C1—F1'	114.7 (11)	C7—C8—H8A	119.6
F2'—C1—F1'	94.2 (9)	C3—C8—H8A	119.6
F1—C1—F1'	56.8 (8)	C5—C9—C10	114.4 (5)
F3—C1—F1'	80.8 (8)	C5—C9—N	112.1 (5)
F3'—C1—C7	116.5 (10)	C10—C9—N	108.0 (5)
F2'—C1—C7	116.5 (9)	C5—C9—H9A	107.3
F1—C1—C7	113.2 (9)	C10—C9—H9A	107.3
F3—C1—C7	117.9 (7)	N—C9—H9A	107.3
F1'—C1—C7	110.3 (8)	C9—C10—H10A	109.5
F3'—C1—F2	59.7 (8)	C9—C10—H10B	109.5
F2'—C1—F2	56.9 (8)	H10A—C10—H10B	109.5
F1—C1—F2	96.9 (8)	C9—C10—H10C	109.5
F3—C1—F2	97.0 (8)	H10A—C10—H10C	109.5
F1'—C1—F2	144.0 (8)	H10B—C10—H10C	109.5
C7—C1—F2	102.4 (8)	N—C11—H11A	109.5
F5—C2—F6'	77.4 (9)	N—C11—H11B	109.5
F5—C2—C3	115.3 (9)	H11A—C11—H11B	109.5
F6'—C2—C3	130.1 (9)	N—C11—H11C	109.5
F5—C2—F4	106.1 (10)	H11A—C11—H11C	109.5
F6'—C2—F4	110.7 (10)	H11B—C11—H11C	109.5
C3—C2—F4	110.8 (10)	C12—O2—H2A	109.5
F5—C2—F6	103.2 (10)	C14—O3—H3A	109.5
C3—C2—F6	109.2 (9)	C15—O5—H5A	109.5
F4—C2—F6	112.1 (8)	O1—C12—O2	120.8 (7)
F5—C2—F4'	116.0 (10)	O1—C12—C13	121.8 (7)
F6'—C2—F4'	91.5 (9)	O2—C12—C13	117.4 (7)
C3—C2—F4'	119.0 (10)	C12—C13—C14	111.8 (5)
F6—C2—F4'	88.8 (8)	C12—C13—H13A	109.3
F6'—C2—F5'	104.7 (10)	C14—C13—H13A	109.3
C3—C2—F5'	107.4 (9)	C12—C13—H13B	109.3
F4—C2—F5'	81.7 (8)	C14—C13—H13B	109.3
F6—C2—F5'	132.1 (11)	H13A—C13—H13B	107.9
F4'—C2—F5'	99.5 (9)	O3—C14—C13	107.7 (4)
C4—C3—C2	124.2 (8)	O3—C14—C15	115.0 (5)
C4—C3—C8	118.5 (8)	C13—C14—C15	109.4 (5)
C2—C3—C8	116.8 (8)	O3—C14—H14A	108.2
C3—C4—C5	121.2 (7)	C13—C14—H14A	108.2
C3—C4—H4A	119.4	C15—C14—H14A	108.2
C5—C4—H4A	119.4	O4—C15—O5	126.3 (6)
C6—C5—C4	118.4 (7)	O4—C15—C14	117.3 (5)
C6—C5—C9	122.5 (7)	O5—C15—C14	116.3 (5)
C4—C5—C9	119.1 (6)

F5—C2—C3—C4	−8.6 (14)	F2—C1—C7—C8	63.3 (12)
F6'—C2—C3—C4	86.2 (14)	F3'—C1—C7—C6	−56.5 (14)
F4—C2—C3—C4	−129.1 (9)	F2'—C1—C7—C6	−177.7 (11)
F6—C2—C3—C4	107.0 (10)	F1—C1—C7—C6	138.1 (10)
F4'—C2—C3—C4	−153.3 (8)	F3—C1—C7—C6	−13.7 (14)
F5'—C2—C3—C4	−41.5 (11)	F1'—C1—C7—C6	76.5 (10)
F5—C2—C3—C8	179.6 (8)	F2—C1—C7—C6	−118.7 (8)
F6'—C2—C3—C8	−85.6 (13)	C6—C7—C8—C3	−0.6 (14)
F4—C2—C3—C8	59.1 (11)	C1—C7—C8—C3	177.4 (8)
F6—C2—C3—C8	−64.8 (10)	C4—C3—C8—C7	2.0 (13)
F4'—C2—C3—C8	34.8 (13)	C2—C3—C8—C7	174.3 (9)
F5'—C2—C3—C8	146.6 (8)	C6—C5—C9—C10	−128.2 (7)
C2—C3—C4—C5	−174.3 (8)	C4—C5—C9—C10	49.9 (8)
C8—C3—C4—C5	−2.6 (11)	C6—C5—C9—N	108.5 (7)
C3—C4—C5—C6	1.8 (11)	C4—C5—C9—N	−73.5 (7)
C3—C4—C5—C9	−176.3 (6)	C11—N—C9—C5	−66.8 (7)
C4—C5—C6—C7	−0.3 (11)	C11—N—C9—C10	166.3 (5)
C9—C5—C6—C7	177.8 (7)	O1—C12—C13—C14	−75.2 (9)
C5—C6—C7—C8	−0.3 (13)	O2—C12—C13—C14	103.5 (7)
C5—C6—C7—C1	−178.4 (8)	C12—C13—C14—O3	−55.0 (7)
F3'—C1—C7—C8	125.5 (13)	C12—C13—C14—C15	70.6 (7)
F2'—C1—C7—C8	4.3 (17)	O3—C14—C15—O4	−167.3 (5)
F1—C1—C7—C8	−39.9 (15)	C13—C14—C15—O4	71.4 (6)
F3—C1—C7—C8	168.3 (10)	O3—C14—C15—O5	9.4 (7)
F1'—C1—C7—C8	−101.5 (12)	C13—C14—C15—O5	−111.9 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···O4ⁱ	0.86	2.37	2.914 (7)	122
N—H0A···O3ⁱⁱ	0.86	2.20	2.887 (7)	137

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₁F₆N·C₄H₆O₅
M_r	405.30
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	6.6770 (13), 8.4510 (17), 16.366 (3)
β (°)	100.05 (3)
V (Å³)	909.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.30 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.957, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	1915, 1757, 1067
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.154, 1.00
No. of reflections	1757
No. of parameters	220
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.27

Computer programs: CAD-4 Software (Enraf–Nonius,1989), CAD-4 Software, XCAD4 (Harms & Wocadlo, 1995), 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
N—H0A···O4ⁱ	0.86	2.37	2.914 (7)	121.7
N—H0A···O3ⁱⁱ	0.86	2.20	2.887 (7)	137.0

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

Acknowledgements

The authors thank the China Postdoctoral Research Fund (20070411010) and the Young Teachers' Starting Fund of Southeast University for support.

References

Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Humphrey, J. M. (2003). Curr. Topics Med. Chem. 3, 1423–1435. Web of Science CrossRef CAS Google Scholar
Lohr, L. (2008). Cancer J. 14, 85–93. Web of Science CrossRef PubMed CAS Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 1| January 2009| Page o197

doi:10.1107/S1600536808043201

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

(S)-1-[3,5-Bis­(tri­fluoro­meth­yl)phen­yl]-N-methylethyl­amine–(R)-2-hy­droxy­butane­dioic acid (1/1)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(S)-1-[3,5-Bis(trifluoromethyl)phenyl]-N-methylethylamine–(R)-2-hydroxybutanedioic acid (1/1)