N-(3,4-Difluoro­phen­yl)-2,2-diphenyl­acetamide

Fun, H.-K.; Ooi, C.W.; Nayak, P.S.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536812014675

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1349-o1350

doi:10.1107/S1600536812014675

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N-(3,4-Difluorophenyl)-2,2-diphenylacetamide

Hoong-Kun Fun,^a ^*‡ Chin Wei Ooi,^a Prakash S. Nayak,^b B. Narayana ^b and B. K. Sarojini ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Montepadavu, PO, Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 26 March 2012; accepted 4 April 2012; online 13 April 2012)

In the title compound, C₂₀H₁₅F₂NO, the mean plane of the acetamide group makes dihedral angles of 88.26 (6), 78.30 (7) and 9.83 (6)° with the two terminal benzene rings and difluoro-substituted benzene ring, respectively. One F atom is disordered over two orientations rotated by 180°, with a site-occupancy ratio of 0.557 (2):0.443 (2). An intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked via N—H⋯O hydrogen bonds into chains along the c axis. The crystal structure is further consolidated by C—H⋯π interactions.

Related literature

For the structural similarity of N-substituted 2-arylacetamides to the lateral chain of natural benzylpenicillin, see: Mijin & Marinkovic (2006 ); Mijin et al. (2008 ). For the coordination abilities of amides, see: Wu et al. (2008 , 2010 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For related structures, see: Praveen et al. (2011a ,b ,c ); Fun et al. (2011a ,b ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₀H₁₅F₂NO
M_r = 323.33
Monoclinic, P 2₁ /c
a = 9.9756 (2) Å
b = 18.0181 (3) Å
c = 9.8107 (2) Å
β = 117.064 (1)°
V = 1570.29 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.54 × 0.41 × 0.37 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.947, T_max = 0.964
30289 measured reflections
6276 independent reflections
4829 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.130
S = 1.03
6276 reflections
231 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1ⁱ	0.881 (15)	2.088 (16)	2.9134 (11)	155.7 (14)
C13—H13A⋯Cg1ⁱⁱ	0.95	2.98	3.7633 (11)	140
C16—H16A⋯Cg2ⁱⁱⁱ	0.95	2.82	3.5998 (15)	140
C20—H20A⋯O1	0.95	2.29	2.8878 (14)	120
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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/S1600536812014675/rz2732sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812014675/rz2732Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812014675/rz2732Isup3.cml

checkCIF report

Comment top

N-Substituted 2-arylacetamides are very interesting compounds because of their structural similarity to the lateral chain of natural benzylpenicillin (Mijin & Marinkovic, 2006; Mijin et al., 2008). Amides are also used as ligands due to their excellent coordination abilities (Wu et al., 2008, 2010). The crystal structures of some acetamide derivatives viz. N-(4-chloro-1,3-benzothiazol-2-yl)-2-(3-methylphenyl)acetamide monohydrate, N-(3-chloro-4-fluorophenyl)-2,2-diphenylacetamide and N-(3-chloro-4-fluorophenyl)-2-(naphthalen-1-yl)acetamide (Praveen et al., 2011a,b,c) have been recently reported. In continuation of our work on the synthesis of amides (Fun et al., 2011a,b), we report herein the crystal structure of the title compound (I).

The molecular structure of the title compound (I) is shown in Fig. 1. The mean plane of the acetamide group (C7/C14/N1/O1) makes dihedral angles of 88.26 (6), 78.30 (7) and 9.83 (6)° with the two terminal benzene rings (C1–C6 and C8–C13) and difluoro-substituted benzene ring (C15–C20), respectively. The F1 fluorine atom is disordered over two orientations rotated by 180° with a site-occupancy ratio of 0.557 (2):0.443 (2). The molecular structure is stabilized by an intramolecular C20—H20A···O1 hydrogen bond which generates an S(6) ring motif (Bernstein et al., 1995). The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to those found in related structures (Praveen et al., 2011a,b,c; Fun et al., 2011a,b). In the crystal structure (Fig. 2), the molecules are linked via intermolecular N1—H1N1···O1 hydrogen bonds (Table 1) into chains along the c axis. The crystal structure is further consolidated by C—H···π interactions (Table 1), involving the C1–C6 ring (centroid Cg 1) and C8—C13 ring (centroid Cg 2).

Related literature top

For the structural similarity of N-substituted 2-arylacetamides to the lateral chain of natural benzylpenicillin, see: Mijin & Marinkovic (2006); Mijin et al. (2008). For the coordination abilities of amides, see: Wu et al. (2008, 2010). For hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see: Praveen et al. (2011a,b,c); Fun et al. (2011a,b). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

Diphenylacetic acid (0.212 g, 1 mmol), 2,6-difluoroaniline (0.1 ml, 1 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.0 g, 0.01 mol) were dissolved in dichloromethane (20 mL). The mixture was stirred in presence of triethylamine at 273 K for about 3 h, then was poured into 100 ml of ice-cold aqueous hydrochloric acid with stirring, and extracted thrice with dichloromethane. The organic layer was washed with a saturated NaHCO₃ solution and brine solution, dried and concentrated under reduced pressure to give the title compound (I). Single crystals were grown from a methylene chloride/N,N-dimethyl formamide mixture (1:1 v/v) by the slow evaporation method (m.p.: 403–405 K).

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 50% probability displacement. An intramolecular hydrogen bond is shown a a dashed line. Bonds invoving the minor component of disorder are shown as open bonds.
	Fig. 2. The crystal packing of the major component of the title compound, viewed along the b axis. H atoms not involved in intermolecular hydrogen interactions (dashed lines) and the minor components of disorder have been omitted for clarity.

N-(3,4-Difluorophenyl)-2,2-diphenylacetamide top

Crystal data top

C₂₀H₁₅F₂NO	F(000) = 672
M_r = 323.33	D_x = 1.368 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9889 reflections
a = 9.9756 (2) Å	θ = 2.3–33.5°
b = 18.0181 (3) Å	µ = 0.10 mm⁻¹
c = 9.8107 (2) Å	T = 100 K
β = 117.064 (1)°	Block, colourless
V = 1570.29 (5) Å³	0.54 × 0.41 × 0.37 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6276 independent reflections
Radiation source: fine-focus sealed tube	4829 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 33.8°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
T_min = 0.947, T_max = 0.964	k = −21→28
30289 measured reflections	l = −15→15

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) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0529P)² + 0.484P] where P = (F_o² + 2F_c²)/3
6276 reflections	(Δ/σ)_max = 0.001
231 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₀H₁₅F₂NO	V = 1570.29 (5) Å³
M_r = 323.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.9756 (2) Å	µ = 0.10 mm⁻¹
b = 18.0181 (3) Å	T = 100 K
c = 9.8107 (2) Å	0.54 × 0.41 × 0.37 mm
β = 117.064 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6276 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4829 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.964	R_int = 0.028
30289 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.35 e Å⁻³
6276 reflections	Δρ_min = −0.22 e Å⁻³
231 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.47032 (19)	0.52149 (9)	0.89774 (16)	0.0561 (5)	0.557 (2)
F1X	0.56321 (18)	0.57786 (10)	0.4987 (2)	0.0389 (5)	0.443 (2)
F2	0.63567 (10)	0.50352 (5)	0.75745 (11)	0.0597 (3)
O1	0.13830 (10)	0.74131 (4)	0.30771 (8)	0.03033 (18)
N1	0.16602 (10)	0.70449 (5)	0.54187 (9)	0.02392 (17)
C1	−0.28769 (13)	0.78053 (6)	0.36744 (13)	0.0319 (2)
H1A	−0.2742	0.8252	0.4238	0.038*
C2	−0.42202 (15)	0.74209 (7)	0.31632 (16)	0.0392 (3)
H2A	−0.4989	0.7598	0.3397	0.047*
C3	−0.44453 (15)	0.67783 (8)	0.23120 (16)	0.0412 (3)
H3A	−0.5370	0.6516	0.1954	0.049*
C4	−0.33179 (16)	0.65211 (7)	0.19871 (15)	0.0409 (3)
H4A	−0.3472	0.6082	0.1397	0.049*
C5	−0.19550 (14)	0.69013 (7)	0.25202 (13)	0.0334 (2)
H5A	−0.1183	0.6718	0.2298	0.040*
C6	−0.17167 (12)	0.75480 (6)	0.33758 (11)	0.02586 (19)
C7	−0.02249 (12)	0.79671 (6)	0.40525 (10)	0.02398 (18)
H7A	0.0016	0.8095	0.5132	0.029*
C8	−0.02398 (12)	0.86899 (5)	0.32524 (11)	0.02398 (18)
C9	0.06364 (13)	0.92810 (6)	0.41162 (12)	0.0299 (2)
H9A	0.1219	0.9227	0.5192	0.036*
C10	0.06666 (15)	0.99493 (6)	0.34203 (14)	0.0344 (2)
H10A	0.1272	1.0348	0.4020	0.041*
C11	−0.01879 (15)	1.00341 (6)	0.18504 (14)	0.0335 (2)
H11A	−0.0178	1.0492	0.1374	0.040*
C12	−0.10549 (13)	0.94485 (6)	0.09827 (13)	0.0315 (2)
H12A	−0.1634	0.9505	−0.0093	0.038*
C13	−0.10860 (12)	0.87771 (6)	0.16718 (11)	0.02652 (19)
H13A	−0.1683	0.8378	0.1066	0.032*
C14	0.10303 (12)	0.74572 (5)	0.41253 (10)	0.02300 (18)
C15	0.28155 (11)	0.65108 (5)	0.58492 (10)	0.02453 (19)
C16	0.31134 (13)	0.61006 (6)	0.71693 (11)	0.0316 (2)
H16A	0.2508	0.6162	0.7679	0.038*
C17	0.43000 (15)	0.56061 (7)	0.77189 (13)	0.0407 (3)
H17A	0.4512	0.5327	0.8616	0.049*	0.443 (2)
C18	0.51753 (15)	0.55115 (7)	0.69909 (15)	0.0426 (3)
C19	0.48590 (14)	0.58994 (7)	0.56743 (14)	0.0370 (3)
H19A	0.5457	0.5822	0.5160	0.044*	0.557 (2)
C20	0.36784 (12)	0.64020 (6)	0.50857 (12)	0.0284 (2)
H20A	0.3463	0.6668	0.4173	0.034*
H1N1	0.1318 (17)	0.7138 (8)	0.6086 (17)	0.038 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0638 (10)	0.0395 (8)	0.0371 (7)	−0.0028 (7)	−0.0014 (7)	0.0203 (6)
F1X	0.0291 (8)	0.0390 (9)	0.0512 (10)	0.0090 (7)	0.0206 (7)	0.0087 (7)
F2	0.0463 (5)	0.0449 (5)	0.0598 (5)	0.0190 (4)	−0.0003 (4)	0.0138 (4)
O1	0.0440 (4)	0.0325 (4)	0.0208 (3)	0.0134 (3)	0.0203 (3)	0.0071 (3)
N1	0.0304 (4)	0.0267 (4)	0.0160 (3)	0.0008 (3)	0.0118 (3)	0.0027 (3)
C1	0.0358 (6)	0.0282 (5)	0.0345 (5)	0.0092 (4)	0.0184 (4)	0.0082 (4)
C2	0.0332 (6)	0.0376 (6)	0.0483 (7)	0.0096 (5)	0.0198 (5)	0.0154 (5)
C3	0.0347 (6)	0.0402 (7)	0.0429 (6)	−0.0029 (5)	0.0126 (5)	0.0131 (5)
C4	0.0485 (7)	0.0336 (6)	0.0398 (6)	−0.0085 (5)	0.0195 (6)	−0.0023 (5)
C5	0.0405 (6)	0.0308 (5)	0.0332 (5)	−0.0027 (5)	0.0205 (5)	−0.0032 (4)
C6	0.0326 (5)	0.0244 (4)	0.0223 (4)	0.0032 (4)	0.0140 (4)	0.0047 (3)
C7	0.0324 (5)	0.0243 (4)	0.0185 (4)	0.0036 (4)	0.0144 (3)	−0.0003 (3)
C8	0.0311 (5)	0.0225 (4)	0.0228 (4)	0.0043 (4)	0.0161 (4)	−0.0008 (3)
C9	0.0409 (6)	0.0266 (5)	0.0263 (4)	−0.0002 (4)	0.0189 (4)	−0.0054 (4)
C10	0.0471 (7)	0.0241 (5)	0.0403 (6)	−0.0028 (5)	0.0271 (5)	−0.0073 (4)
C11	0.0433 (6)	0.0236 (5)	0.0432 (6)	0.0061 (4)	0.0280 (5)	0.0052 (4)
C12	0.0350 (5)	0.0312 (5)	0.0304 (5)	0.0059 (4)	0.0167 (4)	0.0077 (4)
C13	0.0312 (5)	0.0257 (5)	0.0241 (4)	0.0030 (4)	0.0139 (4)	0.0016 (3)
C14	0.0307 (5)	0.0227 (4)	0.0169 (3)	0.0018 (4)	0.0120 (3)	0.0009 (3)
C15	0.0281 (5)	0.0220 (4)	0.0182 (3)	−0.0023 (4)	0.0059 (3)	0.0023 (3)
C16	0.0382 (6)	0.0274 (5)	0.0215 (4)	−0.0067 (4)	0.0069 (4)	0.0051 (4)
C17	0.0451 (7)	0.0289 (6)	0.0278 (5)	−0.0035 (5)	−0.0010 (5)	0.0100 (4)
C18	0.0370 (6)	0.0289 (6)	0.0396 (6)	0.0062 (5)	−0.0020 (5)	0.0058 (5)
C19	0.0332 (6)	0.0319 (6)	0.0374 (6)	0.0046 (5)	0.0086 (5)	0.0013 (4)
C20	0.0304 (5)	0.0270 (5)	0.0244 (4)	0.0035 (4)	0.0094 (4)	0.0035 (3)

Geometric parameters (Å, º) top

F1—C17	1.3157 (17)	C8—C9	1.3938 (15)
F1X—C19	1.253 (2)	C8—C13	1.3967 (13)
F2—C18	1.3561 (14)	C9—C10	1.3913 (16)
O1—C14	1.2316 (11)	C9—H9A	0.9500
N1—C14	1.3533 (12)	C10—C11	1.3883 (18)
N1—C15	1.4107 (14)	C10—H10A	0.9500
N1—H1N1	0.881 (15)	C11—C12	1.3843 (17)
C1—C2	1.3839 (18)	C11—H11A	0.9500
C1—C6	1.3960 (15)	C12—C13	1.3931 (15)
C1—H1A	0.9500	C12—H12A	0.9500
C2—C3	1.385 (2)	C13—H13A	0.9500
C2—H2A	0.9500	C15—C20	1.3882 (15)
C3—C4	1.381 (2)	C15—C16	1.4006 (13)
C3—H3A	0.9500	C16—C17	1.3802 (18)
C4—C5	1.3944 (18)	C16—H16A	0.9500
C4—H4A	0.9500	C17—C18	1.367 (2)
C5—C6	1.3918 (15)	C17—H17A	0.9500
C5—H5A	0.9500	C18—C19	1.3733 (18)
C6—C7	1.5253 (15)	C19—C20	1.3863 (16)
C7—C8	1.5172 (14)	C19—H19A	0.9500
C7—C14	1.5283 (14)	C20—H20A	0.9500
C7—H7A	1.0000

C14—N1—C15	128.51 (8)	C9—C10—H10A	120.0
C14—N1—H1N1	114.9 (10)	C12—C11—C10	119.66 (10)
C15—N1—H1N1	116.6 (10)	C12—C11—H11A	120.2
C2—C1—C6	121.09 (11)	C10—C11—H11A	120.2
C2—C1—H1A	119.5	C11—C12—C13	120.60 (10)
C6—C1—H1A	119.5	C11—C12—H12A	119.7
C1—C2—C3	120.10 (12)	C13—C12—H12A	119.7
C1—C2—H2A	120.0	C12—C13—C8	120.06 (10)
C3—C2—H2A	120.0	C12—C13—H13A	120.0
C4—C3—C2	119.61 (12)	C8—C13—H13A	120.0
C4—C3—H3A	120.2	O1—C14—N1	124.08 (9)
C2—C3—H3A	120.2	O1—C14—C7	122.62 (8)
C3—C4—C5	120.39 (12)	N1—C14—C7	113.25 (8)
C3—C4—H4A	119.8	C20—C15—C16	120.11 (10)
C5—C4—H4A	119.8	C20—C15—N1	123.88 (8)
C6—C5—C4	120.49 (11)	C16—C15—N1	115.95 (9)
C6—C5—H5A	119.8	C17—C16—C15	119.03 (11)
C4—C5—H5A	119.8	C17—C16—H16A	120.5
C5—C6—C1	118.30 (11)	C15—C16—H16A	120.5
C5—C6—C7	122.82 (10)	F1—C17—C18	115.35 (14)
C1—C6—C7	118.83 (9)	F1—C17—C16	123.65 (15)
C8—C7—C6	114.95 (8)	C18—C17—C16	120.96 (11)
C8—C7—C14	110.80 (8)	C18—C17—H17A	119.5
C6—C7—C14	109.82 (8)	C16—C17—H17A	119.5
C8—C7—H7A	107.0	F2—C18—C17	119.82 (12)
C6—C7—H7A	107.0	F2—C18—C19	120.18 (14)
C14—C7—H7A	107.0	C17—C18—C19	120.00 (11)
C9—C8—C13	118.95 (9)	F1X—C19—C18	118.92 (13)
C9—C8—C7	119.05 (9)	F1X—C19—C20	120.23 (13)
C13—C8—C7	121.99 (9)	C18—C19—C20	120.82 (12)
C10—C9—C8	120.71 (10)	C18—C19—H19A	119.6
C10—C9—H9A	119.6	C20—C19—H19A	119.6
C8—C9—H9A	119.6	C19—C20—C15	119.03 (10)
C11—C10—C9	120.01 (11)	C19—C20—H20A	120.5
C11—C10—H10A	120.0	C15—C20—H20A	120.5

C6—C1—C2—C3	−1.41 (17)	C15—N1—C14—O1	1.15 (17)
C1—C2—C3—C4	0.48 (18)	C15—N1—C14—C7	178.67 (9)
C2—C3—C4—C5	0.48 (19)	C8—C7—C14—O1	−37.01 (13)
C3—C4—C5—C6	−0.52 (19)	C6—C7—C14—O1	91.06 (11)
C4—C5—C6—C1	−0.38 (16)	C8—C7—C14—N1	145.43 (9)
C4—C5—C6—C7	177.03 (10)	C6—C7—C14—N1	−86.51 (10)
C2—C1—C6—C5	1.35 (16)	C14—N1—C15—C20	10.68 (16)
C2—C1—C6—C7	−176.17 (10)	C14—N1—C15—C16	−172.12 (10)
C5—C6—C7—C8	106.72 (11)	C20—C15—C16—C17	1.90 (16)
C1—C6—C7—C8	−75.88 (11)	N1—C15—C16—C17	−175.41 (10)
C5—C6—C7—C14	−19.02 (12)	C15—C16—C17—F1	177.53 (13)
C1—C6—C7—C14	158.38 (9)	C15—C16—C17—C18	−0.26 (18)
C6—C7—C8—C9	145.85 (9)	F1—C17—C18—F2	0.46 (19)
C14—C7—C8—C9	−88.93 (10)	C16—C17—C18—F2	178.43 (11)
C6—C7—C8—C13	−35.24 (13)	F1—C17—C18—C19	−179.40 (13)
C14—C7—C8—C13	89.99 (11)	C16—C17—C18—C19	−1.44 (19)
C13—C8—C9—C10	0.23 (16)	F2—C18—C19—F1X	3.4 (2)
C7—C8—C9—C10	179.18 (10)	C17—C18—C19—F1X	−176.70 (14)
C8—C9—C10—C11	0.33 (17)	F2—C18—C19—C20	−178.36 (11)
C9—C10—C11—C12	−0.68 (17)	C17—C18—C19—C20	1.50 (19)
C10—C11—C12—C13	0.46 (17)	F1X—C19—C20—C15	178.32 (14)
C11—C12—C13—C8	0.11 (16)	C18—C19—C20—C15	0.14 (18)
C9—C8—C13—C12	−0.45 (15)	C16—C15—C20—C19	−1.84 (16)
C7—C8—C13—C12	−179.37 (9)	N1—C15—C20—C19	175.24 (10)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.881 (15)	2.088 (16)	2.9134 (11)	155.7 (14)
C13—H13A···Cg1ⁱⁱ	0.95	2.98	3.7633 (11)	140
C16—H16A···Cg2ⁱⁱⁱ	0.95	2.82	3.5998 (15)	140
C20—H20A···O1	0.95	2.29	2.8878 (14)	120

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₅F₂NO
M_r	323.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.9756 (2), 18.0181 (3), 9.8107 (2)
β (°)	117.064 (1)
V (Å³)	1570.29 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.54 × 0.41 × 0.37

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.947, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	30289, 6276, 4829
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.783

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.130, 1.03
No. of reflections	6276
No. of parameters	231
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.22

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.881 (15)	2.088 (16)	2.9134 (11)	155.7 (14)
C13—H13A···Cg1ⁱⁱ	0.9500	2.98	3.7633 (11)	140
C16—H16A···Cg2ⁱⁱⁱ	0.9500	2.82	3.5998 (15)	140
C20—H20A···O1	0.9500	2.2900	2.8878 (14)	120.00

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and CWO thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). CWO also thanks the Malaysian Goverment and USM for the award of the post of Research Officer under Research University Grant No. 1001/PFIZIK/811160. BN thanks the UGC, New Delhi, and the Government of India for the purchase of chemicals through the SAP–DRS–Phase 1 programme.

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Volume 68| Part 5| May 2012| Pages o1349-o1350

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