Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C24H17F10N3O2, exhibits intra­molecular N-H...O hydrogen bonding, as well as intra­molecular Ar...ArF face-to-face inter­actions. The mol­ecules are linked together by N-H...F-C hydrogen bonds, forming chains parallel to the a axis. Adjacent symmetry-related chains are combined in double zipper-like ribbons by parallel ArF...ArF offset [pi]-stacking inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107057939/sf3060sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107057939/sf3060Isup2.hkl
Contains datablock I

CCDC reference: 672567

Comment top

Interest in tris-amine derivatives, RN(CH2CH2NHR')2, has grown steadily over the past two decades. These ligands are widely used to stabilize unusual metal oxidation states and coordination geometry around various metal centres (Fauré et al., 1999; Ward et al., 2002; Gade & Mountford, 2001). Their complexes were applied in several catalytic processes (Gade & Mountford, 2001; Schrodi et al., 2001). Particular attention has been paid to the complexes of fluorinated tris-amine ligands, due to the electron-withdrawal properties of the C6F5-group and additional secondary Ar—F···M interactions (Schrock et al., 1998; Cochran et al., 2000). Here, we report the structure of the title mixed aryl/pentafluoroaryl substituted bis(aminoethyl)carbamate, (I).

As expected for carbamate derivatives, the C11—N1 and C11—O2 bond lengths of (I) are almost equal [1.356 (2) and 1.351 (2) Å, respectively], due to strong conjugation effects (Fig. 1). This causes the central carbamate moiety (N1/O1/O2/C11), together with the adjacent α-carbon atoms (C12/C21/C31), to be planar within 0.110 (1) Å. Compound (I) contains three outward aryl substituents. One of them, the fluorinated ring C23–C28, is linked to the carbamate fragment by a C6F5N—H···O hydrogen bond [2.07 (2) Å]. To the best of our knowledge, similar hydrogen bonding has been observed only once before, in the structure of 2-(pentafluorophenylamino)-pent-2-en-4-one, C6F5NHC(Me)CHCOMe (Gordon et al., 2002). The rotation of the C23–C28 aryl ring around the N2—C23 bond seems to be restricted, due to noticeable conjugation with the neighbouring amine atom N2. This is confirmed by the C24—C23—N2—H2 torsion angle [-5.6 (17)°] and by sufficient shortening of N2—C23 bond distance [1.375 (2) Å]. The other two aryl groups, C13–C18 and C33–C38, are nearly parallel [dihedral angle 11.56 (6)°] and are bonded by the well known Ar···ArF face-to-face interaction (Dunitz, 2004), with a centroid-to-centroid separation of 3.749 Å and a displacement angle (Janiak, 2000) of 15.0°. Thus, the conformation of the molecule of (I) is completely predetermined by the aforementioned intramolecular interactions.

In the crystal structure of (I), translationally related molecules are linked together by C6F5N—H···F—C hydrogen bonds [2.17 (2) Å], forming chains parallel to the a axis (Fig. 2). The low propensity of organic fluorine to participate in hydrogen bonding has been the subject of several reports (Howard et al., 1996; Dunitz & Taylor, 1997). However, in this case, this unusual hydrogen bonding may result from the high acidity of atom H3, caused by the neighbouring highly electron-withdrawing C6F5 group. Adjacent symmetry-related chains are combined in double zipper-like ribbons by parallel ArF···ArF offset π-stacking interactions (Fig. 3). The interplanar ArF···ArF distance is 3.8191 (4) Å, the centroid-to-centroid separation is 3.902 Å and the displacement angle is 25.0°. Finally, these chains are linked by intermolecular Ar···ArF interactions, forming a complex three-dimensional network.

In conclusion, the molecular geometry and crystal packing of (I) are determined by the different types of secondary bonding formed by the C6F5NH– groups.

Related literature top

For related literature, see: Cochran et al. (2000); Dunitz (2004); Dunitz & Taylor (1997); Fauré et al. (1999); Gade & Mountford (2001); Gordon et al. (2002); Howard et al. (1996); Janiak (2000); Schrock et al. (1998); Schrodi et al. (2001); Ward et al. (2002).

Experimental top

The title compound was obtained as a side product from an alkylation reaction of HN(CH2CH2NHC6F5)2 with benzyl chloride in the presence of K2CO3, according to the general method described by Cochran et al. (2000). [Recrystallization from which solvent?]

Refinement top

H atoms were located in a difference Fourier map and refined freely. [Please check added text]

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXTL (Bruker, 2003); program(s) used to refine structure: SHELXTL (Bruker, 2003); molecular graphics: SHELXTL (Bruker, 2003); software used to prepare material for publication: SHELXTL (Bruker, 2003).

Figures top
[Figure 1] Fig. 1. The structure of (I), showing the numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. Dashed lines indicate hydrogen bonds and the Ar···ArF face-to-face interaction.
[Figure 2] Fig. 2. The hydrogen-bonded (dashed lines) chains in (I), parallel to the a axis. H atoms not involved in hydrogen bonds have been omitted.
[Figure 3] Fig. 3. Double zipper-like chains parallel to the a axis. Dashed lines indicate hydrogen bonds and ArF···ArF offset π-stacking interactions. H atoms not involved in hydrogen bonds have been omitted.
Benzyl N,N-bis[2-(pentafluoroanilino)ethyl]carbamate top
Crystal data top
C24H17F10N3O2F(000) = 2304
Mr = 569.41Dx = 1.624 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 8495 reflections
a = 7.6382 (7) Åθ = 2.5–29.8°
b = 14.9272 (15) ŵ = 0.16 mm1
c = 40.857 (4) ÅT = 120 K
V = 4658.4 (8) Å3Block, colourless
Z = 80.30 × 0.20 × 0.20 mm
Data collection top
Bruker SMART 1K
diffractometer
5603 independent reflections
Radiation source: fine-focus sealed tube4174 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
ω scansθmax = 28.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
h = 910
Tmin = 0.925, Tmax = 1.000k = 199
25323 measured reflectionsl = 5348
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102All H-atom parameters refined
S = 1.04 w = 1/[σ2(Fo2) + (0.0347P)2 + 2.4908P]
where P = (Fo2 + 2Fc2)/3
5603 reflections(Δ/σ)max < 0.001
420 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C24H17F10N3O2V = 4658.4 (8) Å3
Mr = 569.41Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 7.6382 (7) ŵ = 0.16 mm1
b = 14.9272 (15) ÅT = 120 K
c = 40.857 (4) Å0.30 × 0.20 × 0.20 mm
Data collection top
Bruker SMART 1K
diffractometer
5603 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
4174 reflections with I > 2σ(I)
Tmin = 0.925, Tmax = 1.000Rint = 0.048
25323 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.102All H-atom parameters refined
S = 1.04Δρmax = 0.25 e Å3
5603 reflectionsΔρmin = 0.27 e Å3
420 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*/Ueq
N10.22240 (19)0.16839 (10)0.14863 (4)0.0215 (3)
N20.4225 (2)0.06994 (11)0.20308 (4)0.0284 (4)
N30.0730 (2)0.28221 (11)0.09205 (4)0.0240 (3)
O10.32683 (17)0.02918 (9)0.13640 (3)0.0284 (3)
O20.06745 (16)0.07645 (8)0.11586 (3)0.0237 (3)
C110.2138 (2)0.08699 (12)0.13402 (4)0.0221 (4)
C120.0422 (3)0.01483 (13)0.10390 (5)0.0292 (4)
C130.1128 (2)0.01703 (11)0.08137 (5)0.0241 (4)
C140.0908 (3)0.04241 (12)0.04890 (5)0.0289 (4)
C150.2351 (3)0.05220 (13)0.02839 (5)0.0318 (5)
C160.4013 (3)0.03634 (13)0.04027 (5)0.0308 (4)
C170.4241 (3)0.00885 (13)0.07244 (5)0.0286 (4)
C180.2811 (3)0.00029 (12)0.09300 (5)0.0254 (4)
C210.3887 (2)0.19409 (13)0.16399 (5)0.0256 (4)
C220.4053 (3)0.16794 (13)0.19981 (5)0.0271 (4)
C230.3807 (2)0.02600 (12)0.23162 (5)0.0245 (4)
C240.3146 (3)0.06146 (13)0.23106 (5)0.0296 (4)
C250.2777 (3)0.10982 (13)0.25884 (5)0.0350 (5)
C260.3033 (3)0.07221 (14)0.28932 (5)0.0367 (5)
C270.3676 (3)0.01344 (14)0.29108 (5)0.0338 (5)
C280.4070 (3)0.06099 (12)0.26309 (5)0.0285 (4)
C310.0755 (2)0.23139 (11)0.15058 (5)0.0214 (4)
C320.0895 (3)0.30861 (12)0.12617 (5)0.0245 (4)
C330.0787 (2)0.25282 (11)0.07725 (4)0.0191 (4)
C340.0692 (2)0.21446 (12)0.04612 (4)0.0228 (4)
C350.2125 (2)0.18822 (11)0.02825 (4)0.0240 (4)
C360.3783 (2)0.19818 (12)0.04110 (4)0.0237 (4)
C370.3928 (2)0.23370 (12)0.07200 (5)0.0226 (4)
C380.2484 (2)0.26037 (11)0.08975 (4)0.0206 (4)
F240.28452 (19)0.09986 (8)0.20144 (3)0.0436 (3)
F250.2119 (2)0.19330 (8)0.25656 (3)0.0569 (4)
F260.2651 (2)0.11886 (9)0.31666 (3)0.0586 (4)
F270.3941 (2)0.05121 (9)0.32056 (3)0.0527 (4)
F280.47823 (18)0.14354 (8)0.26672 (3)0.0420 (3)
F340.09213 (14)0.20300 (8)0.03285 (3)0.0330 (3)
F350.19206 (16)0.15264 (8)0.00181 (3)0.0338 (3)
F360.52101 (14)0.17269 (8)0.02426 (3)0.0336 (3)
F370.55281 (13)0.24290 (9)0.08591 (3)0.0351 (3)
F380.27832 (13)0.29414 (7)0.12014 (2)0.0276 (2)
H20.396 (3)0.0424 (15)0.1852 (6)0.034 (6)*
H30.166 (3)0.2639 (15)0.0824 (6)0.037 (6)*
H140.029 (3)0.0537 (14)0.0414 (5)0.032 (6)*
H150.216 (3)0.0712 (15)0.0075 (6)0.040 (6)*
H160.495 (3)0.0441 (15)0.0263 (6)0.040 (6)*
H170.538 (3)0.0026 (14)0.0802 (5)0.036 (6)*
H180.301 (3)0.0165 (14)0.1155 (6)0.033 (6)*
H1210.151 (3)0.0349 (15)0.0926 (5)0.038 (6)*
H1220.017 (3)0.0534 (14)0.1239 (5)0.032 (6)*
H2110.398 (2)0.2601 (13)0.1628 (5)0.024 (5)*
H2120.482 (3)0.1711 (13)0.1514 (5)0.027 (5)*
H2210.510 (3)0.1978 (13)0.2086 (5)0.026 (5)*
H2220.297 (3)0.1902 (13)0.2127 (5)0.022 (5)*
H3110.031 (3)0.1985 (12)0.1472 (5)0.020 (5)*
H3120.070 (2)0.2555 (13)0.1736 (5)0.022 (5)*
H3220.205 (3)0.3387 (13)0.1280 (5)0.026 (5)*
H3210.002 (3)0.3544 (14)0.1317 (5)0.029 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0217 (7)0.0205 (7)0.0224 (8)0.0012 (6)0.0030 (6)0.0010 (6)
N20.0374 (10)0.0270 (8)0.0208 (9)0.0053 (7)0.0051 (7)0.0006 (7)
N30.0183 (7)0.0299 (8)0.0239 (8)0.0007 (6)0.0001 (6)0.0047 (7)
O10.0313 (7)0.0307 (7)0.0230 (7)0.0096 (6)0.0031 (6)0.0035 (6)
O20.0279 (7)0.0180 (6)0.0252 (7)0.0016 (5)0.0042 (5)0.0029 (5)
C110.0253 (9)0.0245 (9)0.0165 (9)0.0011 (7)0.0016 (7)0.0011 (7)
C120.0337 (11)0.0207 (9)0.0332 (11)0.0025 (8)0.0038 (9)0.0053 (8)
C130.0315 (10)0.0154 (8)0.0254 (10)0.0002 (7)0.0012 (8)0.0024 (7)
C140.0339 (11)0.0247 (9)0.0281 (11)0.0003 (8)0.0059 (9)0.0040 (8)
C150.0508 (13)0.0255 (9)0.0189 (10)0.0032 (9)0.0029 (9)0.0032 (8)
C160.0398 (12)0.0244 (10)0.0284 (11)0.0061 (9)0.0085 (10)0.0019 (8)
C170.0303 (10)0.0268 (10)0.0287 (11)0.0025 (8)0.0024 (9)0.0002 (8)
C180.0375 (11)0.0194 (8)0.0192 (10)0.0006 (8)0.0034 (8)0.0024 (7)
C210.0237 (9)0.0273 (10)0.0259 (10)0.0033 (8)0.0027 (8)0.0014 (8)
C220.0304 (10)0.0262 (9)0.0245 (10)0.0003 (8)0.0073 (8)0.0002 (8)
C230.0246 (9)0.0254 (9)0.0235 (10)0.0060 (8)0.0058 (8)0.0018 (7)
C240.0400 (11)0.0266 (9)0.0221 (10)0.0037 (8)0.0037 (9)0.0065 (8)
C250.0476 (13)0.0232 (10)0.0341 (12)0.0038 (9)0.0027 (10)0.0028 (8)
C260.0527 (14)0.0337 (11)0.0236 (11)0.0020 (10)0.0021 (10)0.0034 (8)
C270.0476 (12)0.0335 (11)0.0203 (10)0.0022 (9)0.0099 (9)0.0061 (8)
C280.0331 (10)0.0236 (9)0.0289 (10)0.0001 (8)0.0106 (9)0.0012 (8)
C310.0244 (9)0.0186 (8)0.0212 (10)0.0000 (7)0.0013 (7)0.0018 (7)
C320.0248 (9)0.0188 (8)0.0299 (10)0.0030 (8)0.0056 (8)0.0023 (7)
C330.0203 (8)0.0182 (8)0.0187 (9)0.0015 (7)0.0004 (7)0.0049 (7)
C340.0219 (9)0.0234 (9)0.0230 (9)0.0044 (7)0.0070 (7)0.0034 (7)
C350.0332 (10)0.0197 (8)0.0192 (9)0.0022 (7)0.0016 (8)0.0004 (7)
C360.0238 (9)0.0222 (9)0.0250 (10)0.0014 (7)0.0049 (7)0.0003 (7)
C370.0177 (8)0.0256 (9)0.0246 (10)0.0012 (7)0.0039 (7)0.0021 (7)
C380.0244 (8)0.0207 (8)0.0167 (9)0.0022 (7)0.0032 (7)0.0004 (7)
F240.0747 (9)0.0309 (6)0.0250 (6)0.0028 (6)0.0042 (6)0.0099 (5)
F250.0976 (12)0.0318 (7)0.0415 (8)0.0218 (7)0.0030 (8)0.0024 (6)
F260.1011 (12)0.0473 (8)0.0272 (7)0.0189 (8)0.0017 (8)0.0077 (6)
F270.0932 (11)0.0439 (7)0.0210 (6)0.0125 (7)0.0138 (7)0.0041 (5)
F280.0636 (9)0.0300 (6)0.0323 (7)0.0119 (6)0.0184 (6)0.0010 (5)
F340.0254 (6)0.0437 (7)0.0298 (6)0.0073 (5)0.0110 (5)0.0007 (5)
F350.0452 (7)0.0344 (6)0.0219 (6)0.0053 (5)0.0039 (5)0.0070 (5)
F360.0303 (6)0.0393 (6)0.0311 (6)0.0062 (5)0.0104 (5)0.0031 (5)
F370.0174 (5)0.0574 (8)0.0307 (6)0.0008 (5)0.0033 (5)0.0023 (6)
F380.0258 (5)0.0372 (6)0.0198 (6)0.0033 (5)0.0025 (4)0.0051 (4)
Geometric parameters (Å, º) top
N1—C111.355 (2)C22—H2210.98 (2)
N1—C311.466 (2)C22—H2221.03 (2)
N1—C211.468 (2)C23—C241.400 (3)
N2—C231.375 (2)C23—C281.402 (3)
N2—C221.475 (2)C24—F241.359 (2)
N2—H20.86 (2)C24—C251.374 (3)
N3—C331.379 (2)C25—F251.347 (2)
N3—C321.454 (2)C25—C261.380 (3)
N3—H30.86 (2)C26—F261.348 (2)
O1—C111.224 (2)C26—C271.372 (3)
O2—C111.351 (2)C27—F271.345 (2)
O2—C121.460 (2)C27—C281.379 (3)
C12—C131.500 (3)C28—F281.355 (2)
C12—H1210.99 (2)C31—C321.528 (2)
C12—H1221.02 (2)C31—H3110.960 (19)
C13—C141.390 (3)C31—H3121.01 (2)
C13—C181.395 (3)C32—H3220.99 (2)
C14—C151.392 (3)C32—H3210.98 (2)
C14—H140.98 (2)C33—C341.397 (2)
C15—C161.380 (3)C33—C381.398 (2)
C15—H150.91 (2)C34—F341.3572 (19)
C16—C171.388 (3)C34—C351.373 (3)
C16—H160.92 (2)C35—F351.347 (2)
C17—C181.384 (3)C35—C361.378 (3)
C17—H170.94 (2)C36—F361.344 (2)
C18—H180.96 (2)C36—C371.374 (3)
C21—C221.520 (3)C37—F371.355 (2)
C21—H2110.99 (2)C37—C381.378 (2)
C21—H2120.94 (2)C38—F381.3592 (19)
C11—N1—C31124.19 (15)N2—C23—C24120.96 (17)
C11—N1—C21117.67 (15)N2—C23—C28124.50 (17)
C31—N1—C21118.13 (14)C24—C23—C28114.46 (17)
C23—N2—C22121.97 (16)F24—C24—C25118.65 (17)
C23—N2—H2115.9 (15)F24—C24—C23117.97 (17)
C22—N2—H2112.1 (15)C25—C24—C23123.38 (18)
C33—N3—C32125.41 (16)F25—C25—C24120.35 (18)
C33—N3—H3113.3 (15)F25—C25—C26119.46 (19)
C32—N3—H3116.9 (15)C24—C25—C26120.17 (18)
C11—O2—C12113.69 (14)F26—C26—C27121.03 (19)
O1—C11—O2123.02 (16)F26—C26—C25120.45 (19)
O1—C11—N1124.25 (17)C27—C26—C25118.52 (19)
O2—C11—N1112.72 (15)F27—C27—C26119.45 (19)
O2—C12—C13109.27 (15)F27—C27—C28119.59 (18)
O2—C12—H121109.0 (13)C26—C27—C28120.95 (18)
C13—C12—H121111.6 (13)F28—C28—C27117.70 (17)
O2—C12—H122106.6 (12)F28—C28—C23119.78 (17)
C13—C12—H122109.3 (12)C27—C28—C23122.50 (18)
H121—C12—H122111.0 (17)N1—C31—C32113.25 (15)
C14—C13—C18119.15 (18)N1—C31—H311108.2 (11)
C14—C13—C12119.77 (18)C32—C31—H311110.6 (11)
C18—C13—C12120.94 (17)N1—C31—H312108.2 (11)
C13—C14—C15120.52 (19)C32—C31—H312110.1 (11)
C13—C14—H14117.2 (12)H311—C31—H312106.3 (15)
C15—C14—H14122.3 (12)N3—C32—C31114.53 (15)
C16—C15—C14119.91 (19)N3—C32—H322105.7 (11)
C16—C15—H15121.9 (15)C31—C32—H322110.8 (12)
C14—C15—H15118.2 (15)N3—C32—H321110.4 (12)
C15—C16—C17119.9 (2)C31—C32—H321109.1 (12)
C15—C16—H16118.2 (14)H322—C32—H321105.9 (16)
C17—C16—H16121.8 (14)N3—C33—C34119.09 (16)
C18—C17—C16120.34 (19)N3—C33—C38126.41 (16)
C18—C17—H17120.5 (14)C34—C33—C38114.45 (16)
C16—C17—H17119.1 (14)F34—C34—C35118.39 (16)
C17—C18—C13120.12 (18)F34—C34—C33117.56 (16)
C17—C18—H18118.6 (13)C35—C34—C33124.04 (16)
C13—C18—H18121.3 (13)F35—C35—C34120.31 (16)
N1—C21—C22114.62 (16)F35—C35—C36119.76 (16)
N1—C21—H211107.6 (11)C34—C35—C36119.93 (16)
C22—C21—H211107.3 (11)F36—C36—C37120.96 (16)
N1—C21—H212108.9 (12)F36—C36—C35121.29 (16)
C22—C21—H212111.7 (12)C37—C36—C35117.75 (16)
H211—C21—H212106.3 (16)F37—C37—C36119.81 (16)
N2—C22—C21110.46 (16)F37—C37—C38118.15 (16)
N2—C22—H221110.2 (11)C36—C37—C38122.04 (16)
C21—C22—H221107.7 (12)F38—C38—C37116.95 (15)
N2—C22—H222110.1 (11)F38—C38—C33121.29 (15)
C21—C22—H222110.0 (11)C37—C38—C33121.75 (16)
H221—C22—H222108.2 (15)
C12—O2—C11—O19.7 (2)F27—C27—C28—F282.6 (3)
C12—O2—C11—N1171.34 (16)C26—C27—C28—F28176.77 (19)
C31—N1—C11—O1168.92 (17)F27—C27—C28—C23179.29 (19)
C21—N1—C11—O19.9 (3)C26—C27—C28—C231.3 (3)
C31—N1—C11—O212.2 (2)N2—C23—C28—F280.1 (3)
C21—N1—C11—O2169.04 (15)C24—C23—C28—F28176.93 (17)
C11—O2—C12—C13174.26 (15)N2—C23—C28—C27178.14 (19)
O2—C12—C13—C14118.74 (19)C24—C23—C28—C271.2 (3)
O2—C12—C13—C1865.6 (2)C11—N1—C31—C32102.95 (19)
C18—C13—C14—C151.3 (3)C21—N1—C31—C3278.3 (2)
C12—C13—C14—C15174.49 (17)C33—N3—C32—C3170.0 (2)
C13—C14—C15—C160.2 (3)N1—C31—C32—N367.2 (2)
C14—C15—C16—C171.3 (3)C32—N3—C33—C34168.50 (16)
C15—C16—C17—C181.9 (3)C32—N3—C33—C3814.2 (3)
C16—C17—C18—C130.8 (3)N3—C33—C34—F344.1 (2)
C14—C13—C18—C170.7 (3)C38—C33—C34—F34178.36 (15)
C12—C13—C18—C17174.97 (17)N3—C33—C34—C35175.66 (17)
C11—N1—C21—C2290.3 (2)C38—C33—C34—C351.9 (3)
C31—N1—C21—C2288.6 (2)F34—C34—C35—F350.5 (2)
C23—N2—C22—C21157.51 (17)C33—C34—C35—F35179.24 (16)
N1—C21—C22—N270.2 (2)F34—C34—C35—C36179.45 (16)
C22—N2—C23—C24148.31 (19)C33—C34—C35—C360.8 (3)
C22—N2—C23—C2834.9 (3)F35—C35—C36—F360.3 (3)
N2—C23—C24—F243.3 (3)C34—C35—C36—F36179.65 (16)
C28—C23—C24—F24179.60 (17)F35—C35—C36—C37179.18 (16)
N2—C23—C24—C25177.17 (19)C34—C35—C36—C370.7 (3)
C28—C23—C24—C250.1 (3)F36—C36—C37—F370.3 (3)
F24—C24—C25—F250.5 (3)C35—C36—C37—F37178.56 (16)
C23—C24—C25—F25179.08 (19)F36—C36—C37—C38179.97 (16)
F24—C24—C25—C26178.7 (2)C35—C36—C37—C381.1 (3)
C23—C24—C25—C260.9 (3)F37—C37—C38—F380.0 (2)
F25—C25—C26—F260.9 (3)C36—C37—C38—F38179.67 (16)
C24—C25—C26—F26179.1 (2)F37—C37—C38—C33179.75 (16)
F25—C25—C26—C27178.9 (2)C36—C37—C38—C330.1 (3)
C24—C25—C26—C270.7 (3)N3—C33—C38—F384.4 (3)
F26—C26—C27—F270.5 (3)C34—C33—C38—F38178.20 (15)
C25—C26—C27—F27179.7 (2)N3—C33—C38—C37175.86 (17)
F26—C26—C27—C28179.8 (2)C34—C33—C38—C371.5 (2)
C25—C26—C27—C280.4 (3)C24—C23—N2—H25.6 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O10.86 (2)2.07 (2)2.886 (2)157 (2)
N3—H3···F37i0.86 (2)2.17 (2)2.9282 (19)147 (2)
Symmetry code: (i) x1, y, z.

Experimental details

Crystal data
Chemical formulaC24H17F10N3O2
Mr569.41
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)120
a, b, c (Å)7.6382 (7), 14.9272 (15), 40.857 (4)
V3)4658.4 (8)
Z8
Radiation typeMo Kα
µ (mm1)0.16
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART 1K
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2003)
Tmin, Tmax0.925, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
25323, 5603, 4174
Rint0.048
(sin θ/λ)max1)0.661
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.102, 1.04
No. of reflections5603
No. of parameters420
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.25, 0.27

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXTL (Bruker, 2003).

Selected geometric parameters (Å, º) top
N1—C111.355 (2)O1—C111.224 (2)
N2—C231.375 (2)O2—C111.351 (2)
N3—C331.379 (2)
C11—N1—C31124.19 (15)C11—O2—C12113.69 (14)
C11—N1—C21117.67 (15)O1—C11—O2123.02 (16)
C31—N1—C21118.13 (14)O1—C11—N1124.25 (17)
C23—N2—C22121.97 (16)O2—C11—N1112.72 (15)
C33—N3—C32125.41 (16)
C24—C23—N2—H25.6 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O10.86 (2)2.07 (2)2.886 (2)157 (2)
N3—H3···F37i0.86 (2)2.17 (2)2.9282 (19)147 (2)
Symmetry code: (i) x1, y, z.
 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

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