2-[3,5-Bis­(4-fluoro­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]-4,6-bis(4-fluoro­phenyl)pyrimidine

Fun, H.-K.; Chia, T.S.; Samshuddin, S.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536812006976

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o807-o808

doi:10.1107/S1600536812006976

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2-[3,5-Bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]-4,6-bis(4-fluorophenyl)pyrimidine

Hoong-Kun Fun,^a ^*‡ Tze Shyang Chia,^a S. Samshuddin,^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, Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 10 February 2012; accepted 16 February 2012; online 24 February 2012)

In the title compound, C₃₁H₂₀F₄N₄, the pyrazole ring adopts an envelope conformation and forms a dihedral angle of 9.91 (6)° with the adjacent pyrimidine ring. The pyrimidine ring forms dihedral angles of 9.23 (6) and 2.16 (5)° with its adjacent fluoro-substituted benzene rings, whereas these angles are 88.22 (6) and 9.66 (6)° for the pyrazole ring and its adjacent benzene rings. In the crystal, molecules are linked by C—H⋯F hydrogen bonds into ribbons along [01-1]. The crystal packing is further stabilized by C—H⋯π and by π–π interactions, with centroid–centroid distances of 3.7428 (7) and 3.7630 (6) Å.

Related literature

For related literature, see: Calabresi et al. (1975 ); El-Hashash et al. (1993 ); Huang & Huang (2002 ); Marquez & Russ (2002 ); Townsend & Drach (2002 ). For related structures and background to various derivatives of 4,4′-difluorochalcone, see: Fun et al. (2010a ,b , 2011 , 2012 ). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ). For ring conformations and ring puckering analysis, see: Cremer & Pople (1975 ). For reference bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₃₁H₂₀F₄N₄
M_r = 524.51
Triclinic, $[P \overline 1]$
a = 10.1020 (1) Å
b = 10.1106 (1) Å
c = 12.3886 (1) Å
α = 104.719 (1)°
β = 98.275 (1)°
γ = 102.167 (1)°
V = 1169.94 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.38 × 0.26 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.959, T_max = 0.987
30262 measured reflections
8234 independent reflections
6443 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.132
S = 1.04
8234 reflections
352 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg5 is the centroid of the C20–C25 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯F4ⁱ	0.93	2.43	3.2759 (16)	151
C31—H31A⋯F3ⁱⁱ	0.93	2.53	3.3208 (14)	143
C1—H1A⋯Cg5ⁱⁱⁱ	0.93	2.98	3.7144 (14)	137
C15—H15A⋯Cg5^iv	0.93	2.74	3.6459 (13)	166
Symmetry codes: (i) x, y-1, z+1; (ii) -x+1, -y+2, -z; (iii) x, y-1, z; (iv) -x+1, -y+1, -z.

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/S1600536812006976/fj2517sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812006976/fj2517Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812006976/fj2517Isup3.cml

checkCIF report

Comment top

The importance of pyrimidines and analogous compounds in pharmaceutical and biological fields is well known (Townsend & Drach, 2002). Some substituted pyrimidines and their derivatives have been reported to possess antimicrobial and antifungal activities (El-Hashash et al., 1993). It has incidental antiviral activity against herpes and vaccinia infections (Calabresi et al., 1975). With the development of clinically useful pyrimidine-based antitumor (Huang & Huang, 2002) and antiviral (Marquez & Russ, 2002) drugs, there has been noticeable interest in synthetic manipulations of pyrimidines. In view of the biological importance of pyrimidines and in continuation of our work on synthesis of various derivatives of 4,4'-difluoro chalcone (Fun et al., 2010a,b;2011;2012), the title compound is prepared and its crystal structure is reported.

The molecular structure of the title compound is shown in Fig. 1. The pyrazole ring (N3/N4/C17–C19) adopts an envelope conformation [puckering parameters Q = 0.1757 (11) Å and ϕ = 135.8 (4)° (Cremer & Pople, 1975)] and forms a dihedral angle of 9.91 (6)° with the adjacent pyrimidine ring (N1/N2/C7–C10) (maximum deviation = 0.011 (1) Å at atom N1). The pyrimidine ring forms dihedral angles of 9.23 (6) and 2.16 (5)° with its adjacent fluoro-substituted benzene rings (C1–C6 & C11–C16, respectively), whereas for pyrazole ring these angles are 88.22 (6) and 9.66 (6)° (C20–C25 & C26–C31, respectively). In the crystal packing, the molecules are linked by intermolecular C—H···F hydrogen bonds into ribbons along [01–1]. The crystal packing is further stabilized by C–H···π interactions (Table 1), involving Cg5 which is the centroid of C20–C25 ring. π–π interactions are also observed with Cg2···Cg4 = 3.7428 (7) Å (symmetry code = 1-X,1-Y,-Z) and Cg2···Cg6 = 3.7630 (6) Å (symmetry code = 2-X,2-Y,-Z), where Cg2, Cg4 and Cg6 are the centroids of N1/N2/C7–C10, C11–C16 and C26–C31 rings, respectively.

Related literature top

For the importance of pyrimidines and related compounds in pharmaceutical and biological fields, see: Calabresi et al. (1975); El-Hashash et al. (1993); Huang & Huang (2002); Marquez & Russ (2002); Townsend & Drach (2002). For related structures and background to various derivatives of 4,4'-difluorochalcone, see: Fun et al. (2010a,b, 2011, 2012). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986). For ring conformations and ring puckering analysis, see: Cremer & Pople (1975). For reference bond lengths, see: Allen et al. (1987).

Experimental top

A mixture of 4,4'-difluoro chalcone (2.44 g, 0.01 mol) and amino guanidine hydrochloride (0.065 g, 0.005 mol) in 25 ml e thanol was refluxed for 24 h in the presence of sodium ethoxide (2 ml). The reaction mixture was cooled to room temperature and refrigerated overnight. The solid product obtained was filtered and recrystallized from ethanol to get a yellow powder. The single crystals were grown from MDC by slow evaporation method and the yield of the compound was 49% (m.p.: 548 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 with atom labels and 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. The dashed lines represent the hydrogen bonds. For clarity sake, hydrogen atoms not involved in hydrogen bonding have been omitted.

2-[3,5-Bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]- 4,6-bis(4-fluorophenyl)pyrimidine top

Crystal data top

C₃₁H₂₀F₄N₄	Z = 2
M_r = 524.51	F(000) = 540
Triclinic, P1	D_x = 1.489 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.1020 (1) Å	Cell parameters from 9041 reflections
b = 10.1106 (1) Å	θ = 2.6–32.2°
c = 12.3886 (1) Å	µ = 0.11 mm⁻¹
α = 104.719 (1)°	T = 100 K
β = 98.275 (1)°	Block, orange
γ = 102.167 (1)°	0.38 × 0.26 × 0.12 mm
V = 1169.94 (2) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	8234 independent reflections
Radiation source: fine-focus sealed tube	6443 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 32.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
T_min = 0.959, T_max = 0.987	k = −15→15
30262 measured reflections	l = −18→18

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.069P)² + 0.3191P] where P = (F_o² + 2F_c²)/3
8234 reflections	(Δ/σ)_max < 0.001
352 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₃₁H₂₀F₄N₄	γ = 102.167 (1)°
M_r = 524.51	V = 1169.94 (2) Å³
Triclinic, P1	Z = 2
a = 10.1020 (1) Å	Mo Kα radiation
b = 10.1106 (1) Å	µ = 0.11 mm⁻¹
c = 12.3886 (1) Å	T = 100 K
α = 104.719 (1)°	0.38 × 0.26 × 0.12 mm
β = 98.275 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	8234 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	6443 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.987	R_int = 0.029
30262 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.04	Δρ_max = 0.47 e Å⁻³
8234 reflections	Δρ_min = −0.23 e Å⁻³
352 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
F1	0.89250 (10)	0.66229 (9)	0.65306 (6)	0.0382 (2)
F2	0.46323 (8)	0.14504 (8)	−0.40779 (6)	0.02907 (17)
F3	0.41746 (8)	1.23828 (8)	0.34142 (7)	0.02823 (17)
F4	0.85454 (8)	1.31912 (8)	−0.39439 (6)	0.02724 (17)
N1	0.80575 (9)	0.81293 (10)	0.19025 (7)	0.01531 (16)
N2	0.73090 (9)	0.71218 (9)	−0.01349 (8)	0.01557 (16)
N3	0.82490 (10)	0.95255 (9)	0.07072 (7)	0.01658 (17)
N4	0.81772 (9)	0.97309 (10)	−0.03568 (7)	0.01557 (17)
C1	0.79155 (15)	0.54528 (13)	0.34519 (10)	0.0270 (3)
H1A	0.7638	0.4614	0.2856	0.032*
C2	0.82258 (16)	0.54050 (14)	0.45700 (11)	0.0333 (3)
H2A	0.8166	0.4545	0.4728	0.040*
C3	0.86230 (14)	0.66581 (14)	0.54355 (10)	0.0255 (2)
C4	0.87484 (13)	0.79565 (13)	0.52391 (10)	0.0235 (2)
H4A	0.9030	0.8790	0.5841	0.028*
C5	0.84417 (12)	0.79855 (12)	0.41174 (10)	0.0210 (2)
H5A	0.8523	0.8852	0.3969	0.025*
C6	0.80148 (11)	0.67431 (11)	0.32098 (9)	0.01634 (19)
C7	0.77219 (10)	0.68237 (11)	0.20211 (9)	0.01509 (18)
C8	0.78434 (10)	0.81953 (11)	0.08231 (9)	0.01468 (18)
C9	0.69487 (10)	0.58258 (11)	−0.00015 (9)	0.01464 (18)
C10	0.71525 (11)	0.56267 (11)	0.10790 (9)	0.01625 (19)
H10A	0.6917	0.4727	0.1169	0.019*
C11	0.63204 (10)	0.46548 (11)	−0.10704 (9)	0.01510 (18)
C12	0.61879 (12)	0.49503 (12)	−0.21201 (9)	0.0189 (2)
H12A	0.6493	0.5878	−0.2137	0.023*
C13	0.56065 (13)	0.38780 (13)	−0.31367 (10)	0.0220 (2)
H13A	0.5510	0.4078	−0.3832	0.026*
C14	0.51758 (12)	0.25068 (12)	−0.30883 (10)	0.0210 (2)
C15	0.52830 (12)	0.21662 (12)	−0.20708 (10)	0.0204 (2)
H15A	0.4980	0.1235	−0.2063	0.025*
C16	0.58535 (11)	0.32499 (12)	−0.10650 (9)	0.0180 (2)
H16A	0.5928	0.3041	−0.0373	0.022*
C17	0.86637 (11)	1.08631 (11)	0.16485 (8)	0.01558 (18)
H17A	0.9378	1.0824	0.2256	0.019*
C18	0.92757 (11)	1.19104 (11)	0.10206 (9)	0.01707 (19)
H18A	0.8960	1.2766	0.1209	0.020*
H18B	1.0280	1.2159	0.1198	0.020*
C19	0.87065 (10)	1.10600 (11)	−0.02133 (9)	0.01479 (18)
C20	0.74267 (11)	1.12033 (11)	0.21187 (9)	0.01539 (18)
C21	0.74268 (11)	1.14552 (12)	0.32750 (9)	0.0183 (2)
H21A	0.8178	1.1375	0.3762	0.022*
C22	0.63167 (12)	1.18269 (12)	0.37163 (9)	0.0207 (2)
H22A	0.6310	1.1975	0.4487	0.025*
C23	0.52321 (11)	1.19689 (12)	0.29813 (10)	0.0206 (2)
C24	0.51718 (12)	1.17086 (12)	0.18210 (10)	0.0211 (2)
H24A	0.4418	1.1796	0.1342	0.025*
C25	0.62721 (11)	1.13136 (12)	0.13951 (9)	0.0185 (2)
H25A	0.6247	1.1118	0.0616	0.022*
C26	0.87168 (10)	1.16138 (11)	−0.11947 (9)	0.01481 (18)
C27	0.92096 (11)	1.30626 (11)	−0.10361 (9)	0.01704 (19)
H27A	0.9579	1.3672	−0.0303	0.020*
C28	0.91544 (12)	1.36053 (12)	−0.19632 (10)	0.0193 (2)
H28A	0.9478	1.4570	−0.1860	0.023*
C29	0.86081 (11)	1.26735 (12)	−0.30369 (9)	0.0193 (2)
C30	0.81118 (12)	1.12320 (12)	−0.32338 (9)	0.0197 (2)
H30A	0.7745	1.0632	−0.3971	0.024*
C31	0.81755 (11)	1.07049 (12)	−0.23047 (9)	0.01756 (19)
H31A	0.7856	0.9737	−0.2419	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0612 (6)	0.0311 (4)	0.0157 (3)	0.0003 (4)	−0.0045 (3)	0.0118 (3)
F2	0.0366 (4)	0.0216 (4)	0.0209 (3)	0.0025 (3)	0.0030 (3)	−0.0020 (3)
F3	0.0246 (3)	0.0301 (4)	0.0304 (4)	0.0098 (3)	0.0107 (3)	0.0046 (3)
F4	0.0355 (4)	0.0302 (4)	0.0214 (3)	0.0086 (3)	0.0041 (3)	0.0180 (3)
N1	0.0177 (4)	0.0148 (4)	0.0152 (4)	0.0044 (3)	0.0035 (3)	0.0072 (3)
N2	0.0183 (4)	0.0132 (4)	0.0158 (4)	0.0036 (3)	0.0034 (3)	0.0059 (3)
N3	0.0254 (4)	0.0127 (4)	0.0124 (4)	0.0038 (3)	0.0040 (3)	0.0057 (3)
N4	0.0196 (4)	0.0151 (4)	0.0140 (4)	0.0047 (3)	0.0043 (3)	0.0071 (3)
C1	0.0418 (7)	0.0163 (5)	0.0174 (5)	−0.0014 (5)	−0.0033 (5)	0.0078 (4)
C2	0.0533 (8)	0.0191 (6)	0.0211 (5)	−0.0027 (5)	−0.0061 (5)	0.0120 (5)
C3	0.0329 (6)	0.0258 (6)	0.0155 (5)	0.0014 (5)	−0.0011 (4)	0.0105 (4)
C4	0.0335 (6)	0.0210 (5)	0.0158 (5)	0.0087 (5)	0.0019 (4)	0.0052 (4)
C5	0.0294 (5)	0.0178 (5)	0.0173 (5)	0.0081 (4)	0.0037 (4)	0.0071 (4)
C6	0.0180 (4)	0.0165 (5)	0.0152 (4)	0.0032 (4)	0.0021 (3)	0.0076 (4)
C7	0.0158 (4)	0.0154 (5)	0.0161 (4)	0.0046 (3)	0.0035 (3)	0.0078 (4)
C8	0.0164 (4)	0.0135 (4)	0.0159 (4)	0.0041 (3)	0.0038 (3)	0.0068 (4)
C9	0.0143 (4)	0.0142 (4)	0.0168 (4)	0.0042 (3)	0.0031 (3)	0.0064 (4)
C10	0.0184 (4)	0.0141 (4)	0.0170 (4)	0.0031 (4)	0.0024 (4)	0.0073 (4)
C11	0.0161 (4)	0.0138 (4)	0.0162 (4)	0.0045 (3)	0.0034 (3)	0.0053 (4)
C12	0.0237 (5)	0.0164 (5)	0.0175 (5)	0.0055 (4)	0.0041 (4)	0.0066 (4)
C13	0.0277 (5)	0.0209 (5)	0.0169 (5)	0.0066 (4)	0.0037 (4)	0.0051 (4)
C14	0.0212 (5)	0.0186 (5)	0.0196 (5)	0.0046 (4)	0.0034 (4)	0.0004 (4)
C15	0.0209 (5)	0.0153 (5)	0.0248 (5)	0.0035 (4)	0.0055 (4)	0.0060 (4)
C16	0.0188 (4)	0.0159 (5)	0.0205 (5)	0.0045 (4)	0.0043 (4)	0.0070 (4)
C17	0.0194 (4)	0.0132 (4)	0.0129 (4)	0.0024 (4)	0.0016 (3)	0.0042 (3)
C18	0.0210 (5)	0.0141 (4)	0.0149 (4)	0.0014 (4)	0.0030 (4)	0.0052 (4)
C19	0.0169 (4)	0.0140 (4)	0.0142 (4)	0.0033 (3)	0.0033 (3)	0.0060 (4)
C20	0.0187 (4)	0.0121 (4)	0.0142 (4)	0.0017 (3)	0.0020 (3)	0.0046 (3)
C21	0.0213 (5)	0.0188 (5)	0.0143 (4)	0.0041 (4)	0.0025 (4)	0.0052 (4)
C22	0.0243 (5)	0.0201 (5)	0.0165 (5)	0.0044 (4)	0.0054 (4)	0.0040 (4)
C23	0.0197 (5)	0.0167 (5)	0.0245 (5)	0.0040 (4)	0.0065 (4)	0.0042 (4)
C24	0.0198 (5)	0.0212 (5)	0.0212 (5)	0.0050 (4)	0.0012 (4)	0.0064 (4)
C25	0.0220 (5)	0.0181 (5)	0.0145 (4)	0.0037 (4)	0.0020 (4)	0.0056 (4)
C26	0.0161 (4)	0.0142 (4)	0.0156 (4)	0.0038 (3)	0.0038 (3)	0.0069 (4)
C27	0.0193 (4)	0.0156 (5)	0.0172 (4)	0.0035 (4)	0.0037 (4)	0.0073 (4)
C28	0.0220 (5)	0.0169 (5)	0.0215 (5)	0.0042 (4)	0.0053 (4)	0.0104 (4)
C29	0.0208 (5)	0.0235 (5)	0.0188 (5)	0.0076 (4)	0.0046 (4)	0.0138 (4)
C30	0.0238 (5)	0.0208 (5)	0.0152 (4)	0.0057 (4)	0.0030 (4)	0.0070 (4)
C31	0.0209 (5)	0.0158 (5)	0.0164 (4)	0.0040 (4)	0.0038 (4)	0.0061 (4)

Geometric parameters (Å, º) top

F1—C3	1.3582 (12)	C13—H13A	0.9300
F2—C14	1.3561 (13)	C14—C15	1.3844 (16)
F3—C23	1.3577 (13)	C15—C16	1.3852 (16)
F4—C29	1.3538 (11)	C15—H15A	0.9300
N1—C7	1.3429 (13)	C16—H16A	0.9300
N1—C8	1.3445 (12)	C17—C20	1.5193 (15)
N2—C8	1.3386 (14)	C17—C18	1.5458 (14)
N2—C9	1.3428 (13)	C17—H17A	0.9800
N3—C8	1.3712 (13)	C18—C19	1.5090 (14)
N3—N4	1.3798 (11)	C18—H18A	0.9700
N3—C17	1.4777 (14)	C18—H18B	0.9700
N4—C19	1.2929 (13)	C19—C26	1.4625 (13)
C1—C2	1.3909 (16)	C20—C21	1.3897 (14)
C1—C6	1.3980 (15)	C20—C25	1.4076 (14)
C1—H1A	0.9300	C21—C22	1.3955 (16)
C2—C3	1.3738 (19)	C21—H21A	0.9300
C2—H2A	0.9300	C22—C23	1.3769 (16)
C3—C4	1.3784 (17)	C22—H22A	0.9300
C4—C5	1.3886 (15)	C23—C24	1.3839 (16)
C4—H4A	0.9300	C24—C25	1.3864 (16)
C5—C6	1.3938 (16)	C24—H24A	0.9300
C5—H5A	0.9300	C25—H25A	0.9300
C6—C7	1.4861 (14)	C26—C27	1.3966 (14)
C7—C10	1.3975 (15)	C26—C31	1.4015 (15)
C9—C10	1.3964 (13)	C27—C28	1.3921 (14)
C9—C11	1.4842 (15)	C27—H27A	0.9300
C10—H10A	0.9300	C28—C29	1.3763 (16)
C11—C12	1.4008 (14)	C28—H28A	0.9300
C11—C16	1.4013 (14)	C29—C30	1.3824 (16)
C12—C13	1.3898 (16)	C30—C31	1.3848 (14)
C12—H12A	0.9300	C30—H30A	0.9300
C13—C14	1.3822 (16)	C31—H31A	0.9300

C7—N1—C8	115.54 (9)	C11—C16—H16A	119.4
C8—N2—C9	116.12 (9)	N3—C17—C20	111.40 (8)
C8—N3—N4	121.04 (9)	N3—C17—C18	100.36 (8)
C8—N3—C17	125.56 (8)	C20—C17—C18	112.75 (8)
N4—N3—C17	113.14 (8)	N3—C17—H17A	110.6
C19—N4—N3	107.85 (8)	C20—C17—H17A	110.6
C2—C1—C6	121.00 (11)	C18—C17—H17A	110.6
C2—C1—H1A	119.5	C19—C18—C17	101.79 (8)
C6—C1—H1A	119.5	C19—C18—H18A	111.4
C3—C2—C1	118.41 (11)	C17—C18—H18A	111.4
C3—C2—H2A	120.8	C19—C18—H18B	111.4
C1—C2—H2A	120.8	C17—C18—H18B	111.4
F1—C3—C2	118.88 (10)	H18A—C18—H18B	109.3
F1—C3—C4	118.40 (11)	N4—C19—C26	120.47 (9)
C2—C3—C4	122.71 (10)	N4—C19—C18	113.62 (8)
C3—C4—C5	118.12 (11)	C26—C19—C18	125.90 (9)
C3—C4—H4A	120.9	C21—C20—C25	118.57 (10)
C5—C4—H4A	120.9	C21—C20—C17	120.88 (9)
C4—C5—C6	121.40 (10)	C25—C20—C17	120.52 (9)
C4—C5—H5A	119.3	C20—C21—C22	120.97 (10)
C6—C5—H5A	119.3	C20—C21—H21A	119.5
C5—C6—C1	118.34 (10)	C22—C21—H21A	119.5
C5—C6—C7	119.64 (9)	C23—C22—C21	118.33 (10)
C1—C6—C7	121.99 (10)	C23—C22—H22A	120.8
N1—C7—C10	121.61 (9)	C21—C22—H22A	120.8
N1—C7—C6	115.61 (9)	F3—C23—C22	118.54 (10)
C10—C7—C6	122.78 (9)	F3—C23—C24	118.54 (10)
N2—C8—N1	127.67 (9)	C22—C23—C24	122.93 (11)
N2—C8—N3	117.20 (9)	C23—C24—C25	117.86 (10)
N1—C8—N3	115.12 (9)	C23—C24—H24A	121.1
N2—C9—C10	121.18 (10)	C25—C24—H24A	121.1
N2—C9—C11	115.31 (9)	C24—C25—C20	121.28 (10)
C10—C9—C11	123.50 (9)	C24—C25—H25A	119.4
C9—C10—C7	117.85 (9)	C20—C25—H25A	119.4
C9—C10—H10A	121.1	C27—C26—C31	119.09 (9)
C7—C10—H10A	121.1	C27—C26—C19	120.48 (9)
C12—C11—C16	118.56 (10)	C31—C26—C19	120.37 (9)
C12—C11—C9	119.53 (9)	C28—C27—C26	120.75 (10)
C16—C11—C9	121.91 (9)	C28—C27—H27A	119.6
C13—C12—C11	120.98 (10)	C26—C27—H27A	119.6
C13—C12—H12A	119.5	C29—C28—C27	118.12 (10)
C11—C12—H12A	119.5	C29—C28—H28A	120.9
C14—C13—C12	118.31 (10)	C27—C28—H28A	120.9
C14—C13—H13A	120.8	F4—C29—C28	118.58 (10)
C12—C13—H13A	120.8	F4—C29—C30	118.33 (10)
F2—C14—C13	118.70 (10)	C28—C29—C30	123.09 (10)
F2—C14—C15	118.61 (10)	C29—C30—C31	118.24 (10)
C13—C14—C15	122.68 (11)	C29—C30—H30A	120.9
C14—C15—C16	118.22 (10)	C31—C30—H30A	120.9
C14—C15—H15A	120.9	C30—C31—C26	120.72 (10)
C16—C15—H15A	120.9	C30—C31—H31A	119.6
C15—C16—C11	121.23 (10)	C26—C31—H31A	119.6
C15—C16—H16A	119.4

C8—N3—N4—C19	−175.75 (9)	C13—C14—C15—C16	−0.36 (17)
C17—N3—N4—C19	9.72 (12)	C14—C15—C16—C11	−0.41 (16)
C6—C1—C2—C3	0.5 (2)	C12—C11—C16—C15	0.57 (16)
C1—C2—C3—F1	179.84 (13)	C9—C11—C16—C15	−179.29 (10)
C1—C2—C3—C4	−1.1 (2)	C8—N3—C17—C20	−71.63 (12)
F1—C3—C4—C5	179.83 (11)	N4—N3—C17—C20	102.61 (9)
C2—C3—C4—C5	0.8 (2)	C8—N3—C17—C18	168.78 (10)
C3—C4—C5—C6	0.17 (19)	N4—N3—C17—C18	−16.98 (11)
C4—C5—C6—C1	−0.74 (18)	N3—C17—C18—C19	16.42 (10)
C4—C5—C6—C7	−178.88 (10)	C20—C17—C18—C19	−102.19 (10)
C2—C1—C6—C5	0.4 (2)	N3—N4—C19—C26	−177.14 (9)
C2—C1—C6—C7	178.49 (12)	N3—N4—C19—C18	2.85 (12)
C8—N1—C7—C10	−1.71 (14)	C17—C18—C19—N4	−13.07 (12)
C8—N1—C7—C6	177.45 (9)	C17—C18—C19—C26	166.92 (10)
C5—C6—C7—N1	7.77 (14)	N3—C17—C20—C21	125.54 (10)
C1—C6—C7—N1	−170.30 (11)	C18—C17—C20—C21	−122.51 (10)
C5—C6—C7—C10	−173.07 (10)	N3—C17—C20—C25	−56.48 (12)
C1—C6—C7—C10	8.86 (17)	C18—C17—C20—C25	55.47 (13)
C9—N2—C8—N1	−0.24 (16)	C25—C20—C21—C22	−0.77 (16)
C9—N2—C8—N3	178.53 (9)	C17—C20—C21—C22	177.25 (10)
C7—N1—C8—N2	1.70 (15)	C20—C21—C22—C23	−1.41 (17)
C7—N1—C8—N3	−177.10 (9)	C21—C22—C23—F3	−177.53 (10)
N4—N3—C8—N2	−3.49 (14)	C21—C22—C23—C24	2.47 (18)
C17—N3—C8—N2	170.33 (9)	F3—C23—C24—C25	178.77 (10)
N4—N3—C8—N1	175.44 (9)	C22—C23—C24—C25	−1.23 (18)
C17—N3—C8—N1	−10.74 (15)	C23—C24—C25—C20	−1.09 (17)
C8—N2—C9—C10	−1.20 (14)	C21—C20—C25—C24	2.06 (16)
C8—N2—C9—C11	178.28 (9)	C17—C20—C25—C24	−175.97 (10)
N2—C9—C10—C7	1.11 (15)	N4—C19—C26—C27	175.99 (10)
C11—C9—C10—C7	−178.34 (9)	C18—C19—C26—C27	−4.00 (16)
N1—C7—C10—C9	0.45 (15)	N4—C19—C26—C31	−1.19 (15)
C6—C7—C10—C9	−178.66 (9)	C18—C19—C26—C31	178.82 (10)
N2—C9—C11—C12	2.11 (14)	C31—C26—C27—C28	0.63 (16)
C10—C9—C11—C12	−178.42 (10)	C19—C26—C27—C28	−176.58 (10)
N2—C9—C11—C16	−178.03 (9)	C26—C27—C28—C29	−0.32 (16)
C10—C9—C11—C16	1.44 (16)	C27—C28—C29—F4	179.78 (10)
C16—C11—C12—C13	0.02 (16)	C27—C28—C29—C30	0.15 (17)
C9—C11—C12—C13	179.89 (10)	F4—C29—C30—C31	−179.93 (10)
C11—C12—C13—C14	−0.74 (17)	C28—C29—C30—C31	−0.31 (17)
C12—C13—C14—F2	−178.73 (10)	C29—C30—C31—C26	0.62 (16)
C12—C13—C14—C15	0.93 (18)	C27—C26—C31—C30	−0.79 (16)
F2—C14—C15—C16	179.29 (10)	C19—C26—C31—C30	176.43 (10)

Hydrogen-bond geometry (Å, º) top

Cg5 is the centroid of the C20–C25 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···F4ⁱ	0.93	2.43	3.2759 (16)	151
C31—H31A···F3ⁱⁱ	0.93	2.53	3.3208 (14)	143
C1—H1A···Cg5ⁱⁱⁱ	0.93	2.98	3.7144 (14)	137
C15—H15A···Cg5^iv	0.93	2.74	3.6459 (13)	166

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

Experimental details

Crystal data
Chemical formula	C₃₁H₂₀F₄N₄
M_r	524.51
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	10.1020 (1), 10.1106 (1), 12.3886 (1)
α, β, γ (°)	104.719 (1), 98.275 (1), 102.167 (1)
V (Å³)	1169.94 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.38 × 0.26 × 0.12

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.959, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	30262, 8234, 6443
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.751

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.132, 1.04
No. of reflections	8234
No. of parameters	352
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.23

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

Hydrogen-bond geometry (Å, º) top

Cg5 is the centroid of the C20–C25 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···F4ⁱ	0.9300	2.4300	3.2759 (16)	151.00
C31—H31A···F3ⁱⁱ	0.9300	2.5300	3.3208 (14)	143.00
C1—H1A···Cg5ⁱⁱⁱ	0.9300	2.98	3.7144 (14)	137
C15—H15A···Cg5^iv	0.9300	2.74	3.6459 (13)	166

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and TSC thank the Universiti Sains Malaysia (USM) for a Research University Grant (No. 1001/PFIZIK/811160). TSC thanks the Malaysian Government and USM for the award of the post of Research Officer under the Research University Grant No. 1001/PSKBP/8630013. BN thanks the UGC for financial assistance through SAP and BSR one-time grant for the purchase of chemicals. SS thanks Mangalore University for the research facilities.

References

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Volume 68| Part 3| March 2012| Pages o807-o808

doi:10.1107/S1600536812006976

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

2-[3,5-Bis­(4-fluoro­phen­yl)-4,5-di­hydro-1H-pyrazol-1-yl]-4,6-bis­(4-fluoro­phenyl)pyrimidine

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

2-[3,5-Bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]-4,6-bis(4-fluorophenyl)pyrimidine