Buy article online - an online subscription or single-article purchase is required to access this article.
share
share
Issue contentsclose
Statistics
close
Download citation
closeDownload citation
Format BIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Text
Plain Text
Supporting information
Supporting informationclose
Download PDF of article
Download PDF of articleclose
Acta Cryst. (2007). E63, o3008
https://doi.org/10.1107/S1600536807024968
Download PDF of article
Download PDF of articleclose
Supporting information
Supporting informationclose
Download citation
closeDownload citation
Format BIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Text
Plain Text
Statistics
close
Issue contentsclose
share
link to html

1-[(6-Chloro­pyridin-3-yl)meth­yl]-4-[2,6-dinitro-4-(trifluoro­meth­yl)phen­yl]­piperazine

M.-Y. Cai, X.-Y. Xu, H.-J. Li, Z.-Y. Zou and L. Li
In the title compound, C17H15ClF3N5O4, the piperazine ring has a chair conformation, with the benzene and pyridine rings attached to the piperazine in equatorial positions. In addition, C—H...N, C—H...O and C—H...F inter­molecular hydrogen bonds link mol­ecules into a two-dimensional network structure. The F atoms are disordered over two sites in an approximately 5:1 ratio.
Read articleSimilar articles

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024968/wk2055sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024968/wk2055Isup2.hkl
Contains datablock I

CCDC reference: 620669

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in main residue
  • R factor = 0.049
  • wR factor = 0.153
  • Data-to-parameter ratio = 11.2

checkCIF/PLATON results

No syntax errors found




Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT301_ALERT_3_C Main Residue  Disorder .........................       9.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  F1      ..       3.18 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5     ..  O4      ..       2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3     ..  F3      ..       2.62 Ang.


Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         94


   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

The derivatives of arylpiperazine are a core fragment of many bioactive compounds and have been widely investigated and found to show a variety of pharmacological effects, such as the ligands of the serotonin receptors (Barbaro et al., 2001; Grundt et al., 2005; Lopez-Rodriguez et al., 2002, respectively). Introduction of an O-substituent in the aryl ring of the arylpiperazine derivative often greatly affects the affinity of the compound for binding the receptor, in part due to the influence of substituent on the compound conformation. As part of our investigation on the stereochemistry of the arylpiperazine derivatives, the crystal structure of the title compound C17H15ClF3N5O4 (I), has been determined.

The molecular structure is shown in Fig. 1. Owing to the delocalization of the π-electrons in the phenyl ring, the bond length of C11—N3 is shorter than a single bond compared with C6—N2, C7—N2, C10—N2, C8—N3 and C9—N3 (Table 1). Additionally, the bond length of C1—N1 is shorter than that of C5—N1 due to the electron-withdrawing effect of Cl1. In the crystal structure (Fig. 2 and Table 2), a weak intermolecular hydrogen-bond contact exists between atoms C3 and F3, forming chains along the c axis. The solid state structure is also enhanced significantly by weak hydrogen-bond C15—H15···O2, C5—H5···O4, C8—H8A···O2 and C13—H13···N1.

Related literature top

For related literature, see: Barbaro et al. (2001); Grundt et al. (2005); Lopez-Rodriguez et al. (2002).

Experimental top

A solution of 6-chloro-3-(chloromethyl)pyridine (2 mmol) in ethanol (10 ml) was added dropwise into a solution of piperazine (4 mmol) and triethylamine (0.2 ml)in ethanol (30 ml) at 323–328 K. Then the mixture was stirred for 5 h at 328 K. After cooling, the mixture was treated with water (50 ml) and extracted with CH2Cl2 (3*50 ml). The organic layer was washed with water, dried over anhydrous Na2SO4, and concentrated to yield 1-((6-chloropyridin-3-yl)methyl)piperazine. A mixture of 2-chloro-1,3-dinitro-5-(trifluoromethyl)benzene (1 mmol), 1-((6-chloropyridin-3-yl)methyl)piperazine (1 mmol), K2CO3 (1 mmol) and dimethylformamide (15 ml) was stirred at 313 K for 3 h. After cooling, the mixture was treated with water (50 ml), and extracted with CH2Cl2 (3*50 ml). The organic layer was washed with water, dried over anhydrous Na2SO4, and concentrated. The residue was chromatographed over a column of silica gel and eluted with petroleum ether-ethyl acetate (4:1 v/v) to give the desired product (51% yield). Single crystals suitable for X-ray analysis were obtained from methanol solution (m.p. 435.7–437.5 K.).

Refinement top

The CF3 disorder was modelled with the 3 Fatoms over 2 sites F1, F2 and F3 and F1', F2', F3' and their occupancies refined competitively to 0.836 (6) and 0.164 (6). The C—F distances were restrained to with 1.27±0.02 Å. All H atom were initially located in a difference Fourier map, placed in geometrically idealized position and constrained to ride on their parent atom with C—H distances in the range 0.86–0.96 Å and Uiso(H) = 1.2eq(C).

Structure description top

The derivatives of arylpiperazine are a core fragment of many bioactive compounds and have been widely investigated and found to show a variety of pharmacological effects, such as the ligands of the serotonin receptors (Barbaro et al., 2001; Grundt et al., 2005; Lopez-Rodriguez et al., 2002, respectively). Introduction of an O-substituent in the aryl ring of the arylpiperazine derivative often greatly affects the affinity of the compound for binding the receptor, in part due to the influence of substituent on the compound conformation. As part of our investigation on the stereochemistry of the arylpiperazine derivatives, the crystal structure of the title compound C17H15ClF3N5O4 (I), has been determined.

The molecular structure is shown in Fig. 1. Owing to the delocalization of the π-electrons in the phenyl ring, the bond length of C11—N3 is shorter than a single bond compared with C6—N2, C7—N2, C10—N2, C8—N3 and C9—N3 (Table 1). Additionally, the bond length of C1—N1 is shorter than that of C5—N1 due to the electron-withdrawing effect of Cl1. In the crystal structure (Fig. 2 and Table 2), a weak intermolecular hydrogen-bond contact exists between atoms C3 and F3, forming chains along the c axis. The solid state structure is also enhanced significantly by weak hydrogen-bond C15—H15···O2, C5—H5···O4, C8—H8A···O2 and C13—H13···N1.

For related literature, see: Barbaro et al. (2001); Grundt et al. (2005); Lopez-Rodriguez et al. (2002).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 2002); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with the atom numbering, showing displacement ellipsoids drawn at the 30% probability level. For clarity, the minor disorder component is omitted.
[Figure 2] Fig. 2. The two-dimensional network structure of (I) formed by intermolecular hydrogen bonding interactions (shown as dashed lines). The minor disorder component is omitted for clarity.
1-[(6-Chloropyridin-3-yl)methyl]-4-[2,6-dinitro-4- (trifluoromethyl)phenyl]piperazine top
Crystal data top
C17H15ClF3N5O4Z = 2
Mr = 445.79F(000) = 456
Triclinic, P1Dx = 1.534 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.131 (2) ÅCell parameters from 4932 reflections
b = 10.171 (3) Åθ = 1.9–24.6°
c = 13.159 (3) ŵ = 0.26 mm−1
α = 79.992 (5)°T = 298 K
β = 73.465 (4)°Block, colorless
γ = 68.099 (4)°0.39 × 0.32 × 0.24 mm
V = 965.2 (4) Å3
Data collection top
Bruker APEX area-detector
diffractometer		3361 independent reflections
Radiation source: fine-focus sealed tube2387 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
φ and ω scansθmax = 25.1°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		h = −9→9
Tmin = 0.901, Tmax = 0.937k = −12→7
4840 measured reflectionsl = −15→14
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0852P)2 + 0.0325P]
where P = (Fo2 + 2Fc2)/3
3361 reflections(Δ/σ)max = 0.001
299 parametersΔρmax = 0.41 e Å−3
94 restraintsΔρmin = −0.28 e Å−3
Crystal data top
C17H15ClF3N5O4γ = 68.099 (4)°
Mr = 445.79V = 965.2 (4) Å3
Triclinic, P1Z = 2
a = 8.131 (2) ÅMo Kα radiation
b = 10.171 (3) ŵ = 0.26 mm−1
c = 13.159 (3) ÅT = 298 K
α = 79.992 (5)°0.39 × 0.32 × 0.24 mm
β = 73.465 (4)°
Data collection top
Bruker APEX area-detector
diffractometer		3361 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		2387 reflections with I > 2σ(I)
Tmin = 0.901, Tmax = 0.937Rint = 0.049
4840 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04994 restraints
wR(F2) = 0.153H-atom parameters constrained
S = 1.09Δρmax = 0.41 e Å−3
3361 reflectionsΔρmin = −0.28 e Å−3
299 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
xyzUiso*/UeqOcc. (<1)
C10.7887 (5)0.7133 (4)0.9578 (3)0.0690 (9)
C20.6835 (5)0.6354 (5)1.0161 (3)0.0755 (10)
H20.59020.67061.07510.091*
C30.7197 (5)0.5047 (4)0.9848 (3)0.0698 (10)
H30.65120.44871.02300.084*
C40.8582 (4)0.4550 (4)0.8963 (2)0.0618 (9)
C50.9543 (5)0.5425 (4)0.8464 (3)0.0711 (10)
H51.05000.50990.78780.085*
C60.8963 (5)0.3145 (4)0.8573 (3)0.0716 (9)
H6A1.02120.28100.81520.086*
H6B0.88450.24610.91780.086*
C70.7992 (5)0.1801 (4)0.7693 (3)0.0687 (9)
H7A0.77620.12290.83530.082*
H7B0.92500.13580.73140.082*
C80.6745 (5)0.1841 (4)0.7032 (2)0.0632 (8)
H8A0.69380.08850.68860.076*
H8B0.54810.22660.74070.076*
C90.6850 (4)0.4126 (3)0.6243 (2)0.0558 (8)
H9A0.55780.45800.65910.067*
H9B0.71290.46710.55760.067*
C100.8044 (4)0.4098 (3)0.6939 (2)0.0574 (8)
H10A0.93160.37220.65610.069*
H10B0.77940.50600.71000.069*
C110.6827 (4)0.2451 (3)0.5118 (2)0.0495 (7)
C120.8179 (4)0.2309 (3)0.4177 (2)0.0512 (7)
C130.8032 (4)0.2031 (3)0.3236 (2)0.0563 (8)
H130.89720.19790.26270.068*
C140.6456 (4)0.1826 (3)0.3203 (2)0.0531 (7)
C150.5092 (4)0.1902 (3)0.4110 (2)0.0555 (8)
H150.40510.17260.41040.067*
C160.5276 (4)0.2240 (3)0.5028 (2)0.0516 (7)
C170.6235 (5)0.1551 (4)0.2189 (3)0.0692 (9)
Cl10.7482 (2)0.87989 (14)0.99492 (11)0.1126 (5)
N10.9221 (4)0.6711 (4)0.8747 (2)0.0763 (9)
N20.7724 (4)0.3222 (3)0.79287 (19)0.0588 (7)
N30.7159 (3)0.2685 (2)0.60416 (18)0.0520 (6)
N40.9940 (4)0.2365 (3)0.4205 (2)0.0644 (7)
N50.3677 (3)0.2454 (4)0.5935 (2)0.0656 (7)
O11.0076 (4)0.3452 (3)0.4285 (2)0.0932 (9)
O21.1174 (4)0.1253 (4)0.4163 (4)0.1380 (14)
O30.2940 (4)0.1571 (3)0.6140 (2)0.0954 (9)
O40.3156 (3)0.3535 (3)0.6374 (2)0.0912 (9)
F10.662 (3)0.0229 (16)0.2097 (13)0.094 (5)0.164 (6)
F20.456 (2)0.194 (2)0.2174 (14)0.097 (5)0.164 (6)
F30.706 (3)0.203 (2)0.1355 (11)0.087 (5)0.164 (6)
F1'0.5160 (7)0.0821 (5)0.2310 (3)0.1118 (14)0.836 (6)
F2'0.5492 (7)0.2745 (4)0.1667 (3)0.1255 (16)0.836 (6)
F3'0.7771 (5)0.0868 (6)0.1564 (3)0.1275 (17)0.836 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.070 (2)0.085 (2)0.0592 (19)−0.0259 (18)−0.0246 (17)−0.0084 (17)
C20.069 (2)0.106 (3)0.0493 (19)−0.028 (2)−0.0090 (16)−0.0140 (19)
C30.067 (2)0.099 (3)0.0507 (19)−0.041 (2)−0.0125 (16)0.0024 (18)
C40.0554 (18)0.081 (2)0.0526 (18)−0.0245 (17)−0.0191 (15)−0.0020 (16)
C50.0573 (19)0.095 (3)0.061 (2)−0.032 (2)−0.0004 (16)−0.0135 (19)
C60.075 (2)0.076 (2)0.065 (2)−0.0225 (19)−0.0247 (18)−0.0008 (17)
C70.087 (2)0.055 (2)0.0597 (19)−0.0256 (18)−0.0173 (18)0.0074 (15)
C80.076 (2)0.0559 (19)0.0567 (19)−0.0302 (16)−0.0053 (16)−0.0038 (14)
C90.0631 (18)0.0478 (17)0.0546 (17)−0.0200 (15)−0.0098 (14)−0.0043 (13)
C100.0621 (18)0.0559 (19)0.0558 (18)−0.0249 (15)−0.0112 (15)−0.0030 (14)
C110.0445 (15)0.0467 (16)0.0552 (17)−0.0161 (13)−0.0057 (13)−0.0078 (12)
C120.0405 (14)0.0585 (18)0.0568 (18)−0.0206 (13)−0.0067 (13)−0.0099 (14)
C130.0496 (16)0.064 (2)0.0549 (18)−0.0234 (15)−0.0032 (14)−0.0094 (14)
C140.0509 (16)0.0524 (17)0.0599 (17)−0.0210 (13)−0.0168 (14)−0.0010 (13)
C150.0449 (16)0.0564 (19)0.070 (2)−0.0232 (14)−0.0165 (15)0.0016 (15)
C160.0377 (14)0.0492 (17)0.0610 (19)−0.0127 (13)−0.0037 (13)−0.0050 (13)
C170.072 (2)0.082 (3)0.065 (2)−0.037 (2)−0.0234 (18)0.0014 (19)
Cl10.1419 (11)0.0949 (9)0.1115 (10)−0.0327 (8)−0.0469 (8)−0.0247 (7)
N10.0707 (19)0.096 (2)0.071 (2)−0.0408 (18)−0.0118 (16)−0.0089 (17)
N20.0673 (16)0.0586 (16)0.0510 (15)−0.0238 (13)−0.0139 (13)−0.0005 (12)
N30.0568 (14)0.0505 (15)0.0481 (14)−0.0226 (12)−0.0048 (11)−0.0057 (11)
N40.0459 (14)0.081 (2)0.0682 (17)−0.0248 (15)−0.0024 (12)−0.0230 (14)
N50.0415 (14)0.076 (2)0.0690 (18)−0.0172 (15)−0.0021 (12)−0.0052 (15)
O10.0840 (17)0.0972 (19)0.119 (2)−0.0597 (16)−0.0191 (15)−0.0056 (16)
O20.0605 (17)0.134 (3)0.235 (4)−0.0209 (18)−0.037 (2)−0.079 (3)
O30.0716 (17)0.102 (2)0.105 (2)−0.0489 (17)0.0107 (15)0.0008 (16)
O40.0546 (14)0.102 (2)0.100 (2)−0.0168 (14)0.0134 (13)−0.0421 (17)
F10.111 (7)0.088 (6)0.088 (7)−0.028 (5)−0.034 (5)−0.016 (4)
F20.090 (6)0.114 (8)0.096 (7)−0.029 (5)−0.040 (5)−0.018 (5)
F30.097 (7)0.096 (7)0.070 (6)−0.042 (5)−0.014 (4)−0.005 (4)
F1'0.140 (3)0.151 (3)0.097 (2)−0.102 (3)−0.041 (2)−0.005 (2)
F2'0.181 (4)0.110 (3)0.098 (2)−0.043 (2)−0.080 (2)0.0219 (18)
F3'0.093 (2)0.196 (4)0.102 (2)−0.027 (2)−0.0241 (18)−0.084 (2)
Geometric parameters (Å, º) top
C1—N11.303 (4)C9—H9B0.9700
C1—C21.367 (5)C10—N21.461 (4)
C1—Cl11.732 (4)C10—H10A0.9700
C2—C31.361 (5)C10—H10B0.9700
C2—H20.9300C11—C121.391 (4)
C3—C41.383 (5)C11—N31.393 (4)
C3—H30.9300C11—C161.395 (4)
C4—C51.363 (5)C12—C131.364 (4)
C4—C61.495 (5)C12—N41.465 (4)
C5—N11.333 (5)C13—C141.386 (4)
C5—H50.9300C13—H130.9300
C6—N21.465 (4)C14—C151.370 (4)
C6—H6A0.9700C14—C171.482 (5)
C6—H6B0.9700C15—C161.373 (4)
C7—N21.455 (4)C15—H150.9300
C7—C81.498 (5)C16—N51.469 (4)
C7—H7A0.9700C17—F31.240 (13)
C7—H7B0.9700C17—F21.275 (14)
C8—N31.458 (4)C17—F11.281 (14)
C8—H8A0.9700N4—O11.177 (4)
C8—H8B0.9700N4—O21.197 (4)
C9—N31.451 (4)N5—O41.207 (4)
C9—C101.503 (4)N5—O31.210 (4)
C9—H9A0.9700
N1—C1—C2124.7 (4)C9—C10—H10A109.4
N1—C1—Cl1115.9 (3)N2—C10—H10B109.4
C2—C1—Cl1119.4 (3)C9—C10—H10B109.4
C3—C2—C1117.8 (3)H10A—C10—H10B108.0
C3—C2—H2121.1C12—C11—N3119.6 (2)
C1—C2—H2121.1C12—C11—C16113.4 (3)
C2—C3—C4120.1 (3)N3—C11—C16126.8 (3)
C2—C3—H3119.9C13—C12—C11124.7 (3)
C4—C3—H3119.9C13—C12—N4117.0 (2)
C5—C4—C3116.1 (3)C11—C12—N4118.1 (3)
C5—C4—C6122.5 (3)C12—C13—C14118.8 (3)
C3—C4—C6121.4 (3)C12—C13—H13120.6
N1—C5—C4125.2 (3)C14—C13—H13120.6
N1—C5—H5117.4C15—C14—C13119.6 (3)
C4—C5—H5117.4C15—C14—C17120.2 (3)
N2—C6—C4112.3 (3)C13—C14—C17120.2 (3)
N2—C6—H6A109.1C14—C15—C16119.3 (3)
C4—C6—H6A109.1C14—C15—H15120.3
N2—C6—H6B109.1C16—C15—H15120.3
C4—C6—H6B109.1C15—C16—C11124.0 (3)
H6A—C6—H6B107.9C15—C16—N5116.2 (3)
N2—C7—C8111.3 (3)C11—C16—N5119.8 (3)
N2—C7—H7A109.4F3—C17—F2108.7 (13)
C8—C7—H7A109.4F3—C17—F1107.3 (12)
N2—C7—H7B109.4F2—C17—F196.7 (13)
C8—C7—H7B109.4F3—C17—C14117.3 (8)
H7A—C7—H7B108.0F2—C17—C14111.8 (8)
N3—C8—C7107.6 (3)F1—C17—C14113.1 (7)
N3—C8—H8A110.2C1—N1—C5116.0 (3)
C7—C8—H8A110.2C7—N2—C10109.8 (2)
N3—C8—H8B110.2C7—N2—C6109.9 (3)
C7—C8—H8B110.2C10—N2—C6110.4 (3)
H8A—C8—H8B108.5C11—N3—C9119.1 (2)
N3—C9—C10109.6 (2)C11—N3—C8120.4 (2)
N3—C9—H9A109.8C9—N3—C8111.0 (2)
C10—C9—H9A109.8O1—N4—O2123.7 (3)
N3—C9—H9B109.8O1—N4—C12120.3 (3)
C10—C9—H9B109.8O2—N4—C12116.0 (3)
H9A—C9—H9B108.2O4—N5—O3125.7 (3)
N2—C10—C9111.0 (2)O4—N5—C16117.0 (3)
N2—C10—H10A109.4O3—N5—C16117.2 (3)
N1—C1—C2—C3−0.4 (5)C13—C14—C17—F198.4 (12)
Cl1—C1—C2—C3−179.8 (3)C15—C14—C17—F3'−149.5 (4)
C1—C2—C3—C4−0.5 (5)C13—C14—C17—F3'31.5 (5)
C2—C3—C4—C51.4 (5)C15—C14—C17—F1'−27.9 (5)
C2—C3—C4—C6−177.4 (3)C13—C14—C17—F1'153.0 (4)
C3—C4—C5—N1−1.6 (5)C15—C14—C17—F2'90.2 (4)
C6—C4—C5—N1177.2 (3)C13—C14—C17—F2'−88.8 (4)
C5—C4—C6—N2−97.5 (4)C2—C1—N1—C50.2 (5)
C3—C4—C6—N281.2 (4)Cl1—C1—N1—C5179.6 (3)
N2—C7—C8—N360.1 (4)C4—C5—N1—C10.8 (5)
N3—C9—C10—N2−56.4 (3)C8—C7—N2—C10−58.3 (4)
N3—C11—C12—C13177.7 (3)C8—C7—N2—C6−179.9 (3)
C16—C11—C12—C131.7 (4)C9—C10—N2—C755.7 (3)
N3—C11—C12—N42.1 (4)C9—C10—N2—C6177.0 (3)
C16—C11—C12—N4−173.9 (3)C4—C6—N2—C7−172.4 (3)
C11—C12—C13—C14−2.1 (5)C4—C6—N2—C1066.4 (4)
N4—C12—C13—C14173.6 (3)C12—C11—N3—C985.1 (3)
C12—C13—C14—C15−0.2 (4)C16—C11—N3—C9−99.5 (3)
C12—C13—C14—C17178.8 (3)C12—C11—N3—C8−131.6 (3)
C13—C14—C15—C162.8 (4)C16—C11—N3—C843.8 (4)
C17—C14—C15—C16−176.2 (3)C10—C9—N3—C11−153.9 (2)
C14—C15—C16—C11−3.3 (5)C10—C9—N3—C859.6 (3)
C14—C15—C16—N5173.5 (3)C7—C8—N3—C11153.2 (3)
C12—C11—C16—C151.0 (4)C7—C8—N3—C9−60.8 (3)
N3—C11—C16—C15−174.6 (3)C13—C12—N4—O1110.7 (4)
C12—C11—C16—N5−175.7 (3)C11—C12—N4—O1−73.3 (4)
N3—C11—C16—N58.7 (5)C13—C12—N4—O2−70.7 (4)
C15—C14—C17—F3151.7 (12)C11—C12—N4—O2105.3 (4)
C13—C14—C17—F3−27.3 (13)C15—C16—N5—O4−128.9 (3)
C15—C14—C17—F225.2 (13)C11—C16—N5—O448.0 (4)
C13—C14—C17—F2−153.8 (12)C15—C16—N5—O347.2 (4)
C15—C14—C17—F1−82.6 (12)C11—C16—N5—O3−135.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···O2i0.972.523.387 (5)149
C13—H13···N1ii0.932.513.331 (4)147
C15—H15···O2iii0.932.543.466 (4)178
C5—H5···O4iv0.932.683.593 (5)166
C3—H3···F3v0.932.623.370 (16)138
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+2, −y+1, −z+1; (iii) x−1, y, z; (iv) x+1, y, z; (v) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC17H15ClF3N5O4
Mr445.79
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)8.131 (2), 10.171 (3), 13.159 (3)
α, β, γ (°)79.992 (5), 73.465 (4), 68.099 (4)
V (Å3)965.2 (4)
Z2
Radiation typeMo Kα
µ (mm−1)0.26
Crystal size (mm)0.39 × 0.32 × 0.24
Data collection
DiffractometerBruker APEX area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.901, 0.937
No. of measured, independent and
observed [I > 2σ(I)] reflections		4840, 3361, 2387
Rint0.049
(sin θ/λ)max (Å−1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.153, 1.09
No. of reflections3361
No. of parameters299
No. of restraints94
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.41, −0.28

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Bruker, 2002), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···O2i0.972.523.387 (5)149.2
C13—H13···N1ii0.932.513.331 (4)146.8
C15—H15···O2iii0.932.543.466 (4)177.9
C5—H5···O4iv0.932.683.593 (5)165.8
C3—H3···F3v0.932.623.370 (16)137.6
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+2, −y+1, −z+1; (iii) x−1, y, z; (iv) x+1, y, z; (v) x, y, z+1.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS