3,5-Bis(4-fluoro­phen­yl)-1-(4-nitro­phen­yl)-4,5-dihydro-1H-pyrazole

Samshuddin, S.; Narayana, B.; Yathirajan, H.S.; Gerber, T.; Hosten, E.; Betz, R.

doi:10.1107/S160053681204370X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Pages o3216-o3217

doi:10.1107/S160053681204370X

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3,5-Bis(4-fluorophenyl)-1-(4-nitrophenyl)-4,5-dihydro-1H-pyrazole

Seranthimata Samshuddin,^a Badiadka Narayana,^a Hemmige S. Yathirajan,^b Thomas Gerber,^c Eric Hosten ^c and Richard Betz ^c ^*

^aMangalore University, Department of Studies in Chemistry, Mangalagangotri 574 199, India, ^bUniversity of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India, and ^cNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
^*Correspondence e-mail: richard.betz@webmail.co.za

(Received 17 October 2012; accepted 22 October 2012; online 27 October 2012)

In the title compound, C₂₁H₁₅F₂N₃O₂, a pyrazole derivative bearing three aromatic substituents, the central five-membered heterocyclic ring makes dihedral angles of 1.77 (14), 3.68 (13) and 72.15 (14)° with the three benzene rings. In the crystal, C—H⋯O and C—H⋯F interactions connect the molecules into double layers parallel to the bc plane.

Related literature

For general information about the pharmacological properties and medical applications of pyrazole derivatives, see: Kumar et al. (2009 ); Sarojini et al. (2010 ); Samshuddin et al. (2012 ). For the crystal structures of other pyrazole derivatives, see: Baktır et al. (2011 ); Jasinski et al. (2012 ). For the puckering analysis of cyclic motifs, see: Cremer & Pople (1975 ). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ); Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₁H₁₅F₂N₃O₂
M_r = 379.36
Monoclinic, P 2₁ /c
a = 13.2884 (13) Å
b = 12.7364 (10) Å
c = 11.4656 (9) Å
β = 115.324 (3)°
V = 1754.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 200 K
0.57 × 0.33 × 0.27 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.692, T_max = 0.971
15973 measured reflections
4301 independent reflections
3066 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.221
S = 1.06
4301 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O2ⁱ	0.95	2.41	3.305 (3)	157
C16—H16⋯F2ⁱⁱ	0.95	2.55	3.427 (3)	154
C26—H26⋯F1ⁱⁱⁱ	0.95	2.56	3.494 (3)	169
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681204370X/is5210sup1.cif

Supporting information file. DOI: 10.1107/S160053681204370X/is5210Isup2.cdx

Structure factors: contains datablock I. DOI: 10.1107/S160053681204370X/is5210Isup3.hkl

Supporting information file. DOI: 10.1107/S160053681204370X/is5210Isup4.cml

checkCIF report

Comment top

Pyrazole derivatives are well known for their broad spectrum of pharmacological properties and have been found – among others – to exhibit antimicrobial, antioxidant, antiamoebic, anti-inflammatory, analgesic, antidepressant and anticancer activity (Kumar et al., 2009; Sarojini et al., 2010; Samshuddin et al., 2012). Because of these various interesting fields of application as well as their fairly assessable path of synthesis, the pyrazoline ring became a center of attraction for organic chemists. The crystal structures of some pyrazolines derived from 4,4'-difluoro chalcone have been reported (Baktır et al., 2011; Jasinski et al., 2012). Fuelled by our ongoing interest in pharmacological active compounds, the title compound was synthesized.

Three phenyl-derived substituents are bonded to a central 4,5-dihydro-1H-pyrazole moiety. The least-squares planes defined by the C11–C16, C31–C36 and C21–C26 benzene rings enclose dihedral angles of 1.77 (14), 3.68 (13) and 72.15 (14)°, respectively, with the least-squares plane defined by the intracyclic atoms of the central five-membered heterocycle with the largest angle formed by one of the two para-fluoro phenyl groups. A conformational analysis of the 4,5-dihydro-1H-pyrazole moiety is precluded due to its low puckering amplitude (Cremer & Pople, 1975). The nitro group is slightly tilted out of plane of the least-square plane defined by the carbon atoms of the aromatic moiety it is bonded to, the corresponding O2—N3—C34—C35 torsion angle being 17.0 (3)° (Fig. 1).

In the crystal, C—H···O and C—H···F contacts can be observed whose range falls by more than 0.1 Å below the sum of van-der-Waals radii of the atoms participating in them. These are exclusively supported by hydrogen atoms bonded to para-fluoro phenyl groups. Metrical parameters as well as information about the symmetry of these contacts are summarized in Table 1. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for the C—H···O contacts is C(12) on the unary level, while the C—H···F contacts necessitate a C(11)C(11) descriptor on the same level. In total, the molecules are connected to double layers parallel to the bc plane. The shortest intercentroid distance between two aromatic systems was measured at 4.8923 (17) Å and is observed between the two different fluorinated phenyl groups in neighbouring molecules. Taking into account the centroid of the 4,5-dihydro-1H-pyrazole moiety as well, the shortest intercentroid distance is found at 3.5918 (15) Å between this pyrazole unit and the nitrated phenyl group (Fig. 2). The packing of the title compound in the crystal structure is shown in Figure 3.

Related literature top

For general information about the pharmacological properties and medical applications of pyrazole derivatives, see: Kumar et al. (2009); Sarojini et al. (2010); Samshuddin et al. (2012). For the crystal structures of other pyrazole derivatives, see: Baktır et al. (2011); Jasinski et al. (2012). For the puckering analysis of cyclic motifs, see: Cremer & Pople (1975). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental top

A mixture of 4,4'-difluoro chalcone (2.68 g, 0.01 mol) and 4-nitrophenyl hydrazine (1.53 g, 0.01 mol) was refluxed in glacial acetic acid (50 ml) for 6 h. The reaction mixture was cooled and pourred into ice-cold water (50 ml). The precipitate was collected by filtration and purified by recrystallization from ethanol (yield: 74%). Yellow blocks, suitable for the X-ray diffraction study, were grown from a DMF solution by slow evaporation at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level).
	Fig. 2. Intermolecular contacts, viewed along [-1 0 0]. For clarity, only an arbitrary selection of intermolecular contacts is shown. [Symmetry codes: (i) x, -y + 1/2, z + 1/2; (ii) x, -y - 1/2, z - 1/2].
	Fig. 3. Molecular packing of the title compound, viewed along [0 1 0] (anisotropic displacement ellipsoids drawn at 50% probability level).

3,5-Bis(4-fluorophenyl)-1-(4-nitrophenyl)-4,5-dihydro-1H-pyrazole top

Crystal data top

C₂₁H₁₅F₂N₃O₂	F(000) = 784
M_r = 379.36	D_x = 1.437 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 443 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.2884 (13) Å	Cell parameters from 6702 reflections
b = 12.7364 (10) Å	θ = 2.3–27.9°
c = 11.4656 (9) Å	µ = 0.11 mm⁻¹
β = 115.324 (3)°	T = 200 K
V = 1754.0 (3) Å³	Block, orange
Z = 4	0.57 × 0.33 × 0.27 mm

Data collection top

Bruker APEXII CCD diffractometer	4301 independent reflections
Radiation source: fine-focus sealed tube	3066 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −17→17
T_min = 0.692, T_max = 0.971	k = −15→16
15973 measured reflections	l = −15→14

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.221	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.1331P)² + 0.5062P] where P = (F_o² + 2F_c²)/3
4301 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₂₁H₁₅F₂N₃O₂	V = 1754.0 (3) Å³
M_r = 379.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.2884 (13) Å	µ = 0.11 mm⁻¹
b = 12.7364 (10) Å	T = 200 K
c = 11.4656 (9) Å	0.57 × 0.33 × 0.27 mm
β = 115.324 (3)°

Data collection top

Bruker APEXII CCD diffractometer	4301 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3066 reflections with I > 2σ(I)
T_min = 0.692, T_max = 0.971	R_int = 0.052
15973 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.221	H-atom parameters constrained
S = 1.06	Δρ_max = 0.41 e Å⁻³
4301 reflections	Δρ_min = −0.39 e Å⁻³
253 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
F1	0.11689 (15)	−0.42461 (13)	−0.04507 (17)	0.0638 (5)
F2	0.01460 (13)	0.43563 (13)	0.35591 (18)	0.0611 (5)
O1	0.61528 (16)	0.02802 (17)	1.00769 (16)	0.0536 (5)
O2	0.57223 (18)	0.19339 (18)	0.98021 (18)	0.0663 (6)
N1	0.30617 (15)	−0.05788 (13)	0.36124 (16)	0.0305 (4)
N2	0.32892 (15)	0.04326 (14)	0.40815 (16)	0.0327 (4)
N3	0.56940 (16)	0.10368 (18)	0.93869 (18)	0.0428 (5)
C1	0.25491 (17)	−0.05414 (16)	0.23711 (18)	0.0297 (4)
C2	0.2351 (2)	0.05569 (17)	0.1837 (2)	0.0368 (5)
H2A	0.1545	0.0717	0.1396	0.044*
H2B	0.2688	0.0663	0.1225	0.044*
C3	0.29364 (18)	0.12390 (17)	0.30617 (19)	0.0322 (5)
H3	0.3607	0.1583	0.3047	0.039*
C11	0.21963 (17)	−0.15094 (17)	0.16168 (18)	0.0298 (4)
C12	0.24429 (19)	−0.24829 (18)	0.2240 (2)	0.0354 (5)
H12	0.2849	−0.2511	0.3151	0.042*
C13	0.2103 (2)	−0.34014 (19)	0.1545 (3)	0.0426 (5)
H13	0.2270	−0.4063	0.1968	0.051*
C14	0.1515 (2)	−0.3339 (2)	0.0222 (2)	0.0431 (6)
C15	0.1269 (2)	−0.2404 (2)	−0.0425 (2)	0.0437 (6)
H15	0.0871	−0.2385	−0.1338	0.052*
C16	0.16125 (19)	−0.14838 (19)	0.0279 (2)	0.0375 (5)
H16	0.1448	−0.0827	−0.0156	0.045*
C21	0.21828 (17)	0.20653 (17)	0.32160 (18)	0.0303 (4)
C22	0.2177 (2)	0.30641 (19)	0.2750 (3)	0.0495 (6)
H22	0.2653	0.3225	0.2350	0.059*
C23	0.1486 (3)	0.3840 (2)	0.2857 (3)	0.0570 (7)
H23	0.1479	0.4525	0.2528	0.068*
C24	0.08164 (19)	0.35925 (19)	0.3447 (3)	0.0422 (6)
C25	0.0790 (2)	0.2616 (2)	0.3912 (2)	0.0431 (6)
H25	0.0308	0.2464	0.4309	0.052*
C26	0.14779 (19)	0.18489 (19)	0.3796 (2)	0.0390 (5)
H26	0.1468	0.1163	0.4117	0.047*
C31	0.39135 (16)	0.05788 (16)	0.53770 (18)	0.0289 (4)
C32	0.42036 (18)	−0.02827 (17)	0.62266 (19)	0.0321 (4)
H32	0.3995	−0.0972	0.5896	0.039*
C33	0.47889 (18)	−0.01300 (18)	0.7534 (2)	0.0344 (5)
H33	0.4983	−0.0711	0.8108	0.041*
C34	0.50939 (17)	0.08796 (18)	0.80077 (19)	0.0331 (5)
C35	0.48391 (18)	0.17349 (18)	0.7191 (2)	0.0348 (5)
H35	0.5063	0.2419	0.7534	0.042*
C36	0.42597 (18)	0.15954 (18)	0.5877 (2)	0.0346 (5)
H36	0.4095	0.2181	0.5311	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0698 (11)	0.0542 (10)	0.0696 (11)	−0.0138 (8)	0.0319 (9)	−0.0309 (8)
F2	0.0490 (9)	0.0516 (10)	0.0853 (12)	0.0049 (7)	0.0312 (9)	−0.0195 (8)
O1	0.0509 (10)	0.0741 (14)	0.0274 (8)	0.0024 (9)	0.0089 (7)	−0.0019 (8)
O2	0.0681 (13)	0.0731 (14)	0.0428 (10)	0.0056 (11)	0.0096 (9)	−0.0301 (10)
N1	0.0346 (9)	0.0314 (9)	0.0248 (8)	0.0006 (7)	0.0119 (7)	−0.0021 (7)
N2	0.0425 (10)	0.0293 (9)	0.0234 (8)	0.0018 (7)	0.0113 (7)	0.0009 (7)
N3	0.0354 (10)	0.0617 (14)	0.0292 (9)	−0.0014 (9)	0.0117 (8)	−0.0124 (9)
C1	0.0316 (10)	0.0352 (11)	0.0239 (9)	0.0015 (8)	0.0133 (8)	−0.0014 (8)
C2	0.0474 (13)	0.0379 (12)	0.0248 (9)	0.0063 (10)	0.0151 (9)	0.0025 (8)
C3	0.0356 (11)	0.0350 (11)	0.0267 (9)	0.0027 (8)	0.0139 (8)	0.0035 (8)
C11	0.0301 (10)	0.0366 (11)	0.0233 (9)	0.0008 (8)	0.0121 (8)	−0.0025 (8)
C12	0.0364 (11)	0.0373 (11)	0.0308 (10)	0.0015 (9)	0.0127 (9)	0.0014 (9)
C13	0.0449 (13)	0.0362 (12)	0.0505 (14)	0.0009 (10)	0.0240 (11)	−0.0002 (10)
C14	0.0418 (13)	0.0435 (13)	0.0490 (13)	−0.0072 (10)	0.0243 (11)	−0.0179 (11)
C15	0.0465 (14)	0.0559 (15)	0.0288 (10)	−0.0052 (11)	0.0162 (10)	−0.0114 (10)
C16	0.0428 (12)	0.0456 (13)	0.0233 (9)	0.0011 (10)	0.0132 (9)	−0.0011 (9)
C21	0.0319 (10)	0.0334 (11)	0.0261 (9)	−0.0009 (8)	0.0128 (8)	−0.0010 (8)
C22	0.0518 (15)	0.0375 (13)	0.0737 (18)	0.0024 (11)	0.0408 (14)	0.0105 (12)
C23	0.0619 (17)	0.0300 (13)	0.091 (2)	0.0033 (12)	0.0439 (16)	0.0080 (13)
C24	0.0311 (11)	0.0396 (13)	0.0511 (14)	0.0004 (9)	0.0132 (10)	−0.0151 (10)
C25	0.0375 (12)	0.0548 (15)	0.0420 (12)	0.0000 (10)	0.0217 (10)	−0.0030 (11)
C26	0.0415 (12)	0.0412 (12)	0.0392 (11)	−0.0023 (10)	0.0221 (10)	0.0042 (9)
C31	0.0287 (10)	0.0344 (11)	0.0251 (9)	0.0009 (8)	0.0128 (8)	−0.0020 (8)
C32	0.0363 (11)	0.0330 (11)	0.0255 (9)	−0.0020 (8)	0.0118 (8)	−0.0023 (8)
C33	0.0369 (11)	0.0404 (12)	0.0256 (9)	−0.0004 (9)	0.0132 (8)	0.0004 (8)
C34	0.0273 (10)	0.0460 (12)	0.0244 (9)	0.0007 (9)	0.0094 (8)	−0.0073 (9)
C35	0.0317 (11)	0.0355 (11)	0.0376 (11)	−0.0023 (9)	0.0151 (9)	−0.0097 (9)
C36	0.0332 (11)	0.0354 (11)	0.0355 (11)	−0.0003 (9)	0.0150 (9)	−0.0007 (9)

Geometric parameters (Å, º) top

F1—C14	1.356 (3)	C15—C16	1.385 (3)
F2—C24	1.362 (3)	C15—H15	0.9500
O1—N3	1.230 (3)	C16—H16	0.9500
O2—N3	1.232 (3)	C21—C22	1.378 (3)
N1—C1	1.289 (2)	C21—C26	1.388 (3)
N1—N2	1.379 (2)	C22—C23	1.389 (4)
N2—C31	1.369 (2)	C22—H22	0.9500
N2—C3	1.474 (3)	C23—C24	1.364 (4)
N3—C34	1.448 (3)	C23—H23	0.9500
C1—C11	1.463 (3)	C24—C25	1.360 (4)
C1—C2	1.504 (3)	C25—C26	1.383 (3)
C2—C3	1.548 (3)	C25—H25	0.9500
C2—H2A	0.9900	C26—H26	0.9500
C2—H2B	0.9900	C31—C32	1.407 (3)
C3—C21	1.514 (3)	C31—C36	1.411 (3)
C3—H3	1.0000	C32—C33	1.376 (3)
C11—C16	1.392 (3)	C32—H32	0.9500
C11—C12	1.398 (3)	C33—C34	1.387 (3)
C12—C13	1.378 (3)	C33—H33	0.9500
C12—H12	0.9500	C34—C35	1.381 (3)
C13—C14	1.380 (4)	C35—C36	1.379 (3)
C13—H13	0.9500	C35—H35	0.9500
C14—C15	1.367 (4)	C36—H36	0.9500

C1—N1—N2	108.68 (16)	C15—C16—H16	119.6
C31—N2—N1	118.70 (16)	C11—C16—H16	119.6
C31—N2—C3	127.24 (18)	C22—C21—C26	118.4 (2)
N1—N2—C3	113.53 (16)	C22—C21—C3	119.40 (18)
O1—N3—O2	123.6 (2)	C26—C21—C3	122.22 (19)
O1—N3—C34	118.9 (2)	C21—C22—C23	121.1 (2)
O2—N3—C34	117.5 (2)	C21—C22—H22	119.4
N1—C1—C11	120.38 (18)	C23—C22—H22	119.4
N1—C1—C2	113.68 (18)	C24—C23—C22	118.4 (2)
C11—C1—C2	125.93 (17)	C24—C23—H23	120.8
C1—C2—C3	102.70 (16)	C22—C23—H23	120.8
C1—C2—H2A	111.2	C25—C24—F2	119.2 (2)
C3—C2—H2A	111.2	C25—C24—C23	122.5 (2)
C1—C2—H2B	111.2	F2—C24—C23	118.3 (2)
C3—C2—H2B	111.2	C24—C25—C26	118.6 (2)
H2A—C2—H2B	109.1	C24—C25—H25	120.7
N2—C3—C21	113.17 (16)	C26—C25—H25	120.7
N2—C3—C2	101.21 (16)	C25—C26—C21	121.0 (2)
C21—C3—C2	113.27 (18)	C25—C26—H26	119.5
N2—C3—H3	109.6	C21—C26—H26	119.5
C21—C3—H3	109.6	N2—C31—C32	120.28 (18)
C2—C3—H3	109.6	N2—C31—C36	120.42 (19)
C16—C11—C12	118.82 (19)	C32—C31—C36	119.30 (19)
C16—C11—C1	121.22 (19)	C33—C32—C31	120.3 (2)
C12—C11—C1	119.97 (18)	C33—C32—H32	119.9
C13—C12—C11	120.7 (2)	C31—C32—H32	119.9
C13—C12—H12	119.7	C32—C33—C34	119.5 (2)
C11—C12—H12	119.7	C32—C33—H33	120.3
C12—C13—C14	118.5 (2)	C34—C33—H33	120.3
C12—C13—H13	120.7	C35—C34—C33	121.33 (19)
C14—C13—H13	120.7	C35—C34—N3	119.5 (2)
F1—C14—C15	119.3 (2)	C33—C34—N3	119.2 (2)
F1—C14—C13	118.1 (2)	C36—C35—C34	120.0 (2)
C15—C14—C13	122.6 (2)	C36—C35—H35	120.0
C14—C15—C16	118.6 (2)	C34—C35—H35	120.0
C14—C15—H15	120.7	C35—C36—C31	119.6 (2)
C16—C15—H15	120.7	C35—C36—H36	120.2
C15—C16—C11	120.8 (2)	C31—C36—H36	120.2

C1—N1—N2—C31	−174.73 (17)	C2—C3—C21—C26	85.0 (2)
C1—N1—N2—C3	−2.4 (2)	C26—C21—C22—C23	0.1 (4)
N2—N1—C1—C11	−179.48 (17)	C3—C21—C22—C23	179.1 (3)
N2—N1—C1—C2	−0.7 (2)	C21—C22—C23—C24	0.6 (5)
N1—C1—C2—C3	3.2 (2)	C22—C23—C24—C25	−1.0 (4)
C11—C1—C2—C3	−178.07 (19)	C22—C23—C24—F2	179.5 (3)
C31—N2—C3—C21	−62.7 (3)	F2—C24—C25—C26	−179.8 (2)
N1—N2—C3—C21	125.73 (19)	C23—C24—C25—C26	0.8 (4)
C31—N2—C3—C2	175.7 (2)	C24—C25—C26—C21	0.0 (4)
N1—N2—C3—C2	4.2 (2)	C22—C21—C26—C25	−0.4 (3)
C1—C2—C3—N2	−4.1 (2)	C3—C21—C26—C25	−179.3 (2)
C1—C2—C3—C21	−125.55 (18)	N1—N2—C31—C32	−7.3 (3)
N1—C1—C11—C16	178.05 (19)	C3—N2—C31—C32	−178.48 (19)
C2—C1—C11—C16	−0.6 (3)	N1—N2—C31—C36	173.54 (18)
N1—C1—C11—C12	−1.8 (3)	C3—N2—C31—C36	2.4 (3)
C2—C1—C11—C12	179.6 (2)	N2—C31—C32—C33	−177.13 (19)
C16—C11—C12—C13	−0.8 (3)	C36—C31—C32—C33	2.0 (3)
C1—C11—C12—C13	179.1 (2)	C31—C32—C33—C34	−0.2 (3)
C11—C12—C13—C14	0.0 (3)	C32—C33—C34—C35	−1.2 (3)
C12—C13—C14—F1	−179.0 (2)	C32—C33—C34—N3	178.99 (18)
C12—C13—C14—C15	0.8 (4)	O1—N3—C34—C35	−162.4 (2)
F1—C14—C15—C16	178.9 (2)	O2—N3—C34—C35	17.0 (3)
C13—C14—C15—C16	−0.9 (4)	O1—N3—C34—C33	17.4 (3)
C14—C15—C16—C11	0.1 (3)	O2—N3—C34—C33	−163.2 (2)
C12—C11—C16—C15	0.7 (3)	C33—C34—C35—C36	0.7 (3)
C1—C11—C16—C15	−179.1 (2)	N3—C34—C35—C36	−179.45 (18)
N2—C3—C21—C22	151.6 (2)	C34—C35—C36—C31	1.1 (3)
C2—C3—C21—C22	−94.0 (3)	N2—C31—C36—C35	176.68 (18)
N2—C3—C21—C26	−29.5 (3)	C32—C31—C36—C35	−2.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2ⁱ	0.95	2.41	3.305 (3)	157
C16—H16···F2ⁱⁱ	0.95	2.55	3.427 (3)	154
C26—H26···F1ⁱⁱⁱ	0.95	2.56	3.494 (3)	169

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₅F₂N₃O₂
M_r	379.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	13.2884 (13), 12.7364 (10), 11.4656 (9)
β (°)	115.324 (3)
V (Å³)	1754.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.57 × 0.33 × 0.27

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.692, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	15973, 4301, 3066
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.221, 1.06
No. of reflections	4301
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.39

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2ⁱ	0.95	2.41	3.305 (3)	157
C16—H16···F2ⁱⁱ	0.95	2.55	3.427 (3)	154
C26—H26···F1ⁱⁱⁱ	0.95	2.56	3.494 (3)	169

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

Acknowledgements

BN thanks the UGC for financial assistance through a BSR one-time grant for the purchase of chemicals. SS thanks Mangalore University for the research facilities.

References

Baktır, Z., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o1292–o1293. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Jasinski, J. P., Golen, J. A., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2012). Crystals, 2, 1108–1115. CrossRef CAS Google Scholar
Kumar, S., Bawa, S., Drabu, S., Kumar, R. & Gupta, H. (2009). Recent Pat. Anti-infect. Drug Discov. 4, 154–163. CrossRef PubMed CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Samshuddin, S., Narayana, B., Sarojini, B. K., Khan, M. T. H., Yathirajan, H. S., Raj, C. G. D. & Raghavendra, R. (2012). Med. Chem. Res. 21, 2012–2022. Web of Science CSD CrossRef CAS Google Scholar
Sarojini, B. K., Vidyagayatri, M., Darshanraj, C. G., Bharath, B. R. & Manjunatha, H. (2010). Lett. Drug Des. Discov. 7, 214–224. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar