PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. Sep 1, 2012; 68(Pt 9): o2680.
Published online Aug 11, 2012. doi:  10.1107/S160053681203454X
PMCID: PMC3435702
5-(4-Bromo­phen­yl)-3-(4-fluoro­phen­yl)-1-phenyl-4,5-dihydro-1H-pyrazole
Hoong-Kun Fun,a* Tze Shyang Chia,a M. Sapnakumari,b B. Narayana,b and B. K. Sarojinic
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
cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India
Correspondence e-mail: hkfun/at/usm.my
Thomson Reuters ResearcherID: A-3561-2009.
Received July 26, 2012; Accepted August 3, 2012.
In the title compound, C21H16BrFN2, the fluoro-substituted benzene ring is disordered over two orientations about the C—F bond and the C—C bond between the benzene and pyrazole groups with a site-occupancy ratio of 0.516 (8):0.484 (8). The central pyrazole ring [maximum deviation = 0.035 (3) Å] makes dihedral angles of 22.4 (2), 11.0 (2), 77.19 (16) and 7.44 (17)° with the two disorder components of the benzene ring, the bromo-substituted benzene ring and the phenyl ring, respectively. In the crystal, mol­ecules are linked into a layer parallel to the bc plane through C—H(...)π inter­actions.
Related literature  
For background to pyrazoline derivatives, see: Fun et al. (2010 [triangle]); Samshuddin et al. (2010 [triangle], 2011 [triangle]). For a related structure, see: Samshuddin et al. (2010 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]).
An external file that holds a picture, illustration, etc.
Object name is e-68-o2680-scheme1.jpg Object name is e-68-o2680-scheme1.jpg
Crystal data  
  • C21H16BrFN2
  • M r = 395.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-68-o2680-efi1.jpg
  • a = 20.5345 (5) Å
  • b = 5.2689 (1) Å
  • c = 16.1929 (5) Å
  • β = 104.443 (2)°
  • V = 1696.61 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.44 mm−1
  • T = 100 K
  • 0.25 × 0.13 × 0.09 mm
Data collection  
  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.583, T max = 0.818
  • 16716 measured reflections
  • 4974 independent reflections
  • 3761 reflections with I > 2σ(I)
  • R int = 0.048
Refinement  
  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.113
  • S = 1.01
  • 4974 reflections
  • 263 parameters
  • 130 restraints
  • H-atom parameters constrained
  • Δρmax = 1.26 e Å−3
  • Δρmin = −0.99 e Å−3
Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).
Table 1
Table 1
Hydrogen-bond geometry (Å, °)
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681203454X/is5174sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203454X/is5174Isup2.hkl
Supplementary material file. DOI: 10.1107/S160053681203454X/is5174Isup3.cml
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC also thanks the Malaysian Government and USM for the award of a research fellowship. BN thanks the UGC for financial assistance through the SAP and BSR one-time grant for the purchase of chemicals.
supplementary crystallographic information
Comment
In continuation of our work on synthesis of pyrazoline derivatives (Fun et al., 2010; Samshuddin et al., 2010, 2011), the title compound was prepared and its crystal structure is now reported.
The asymmetric unit of the title compound is shown in Fig. 1. The fluoro-substituted benzene ring is disordered over two positions (C16–C21 and C16/C17X/C18X/C19/C20X/C21X) rotated about the C9—C16···C19—F1 axis with a site-occupancy ratio of 0.516 (8):0.484 (8). The central pyrazole ring [N1/N2/C7–C9; maximum deviation = 0.035 (3) Å at atom C7] makes dihedral angles of 77.19 (16), 7.44 (17), 22.4 (2) and 11.0 (2)° with the C1–C6 (A), C10–C15 (B), C16–C21 (C) and C16/C17X/C18X/C19/C20X/C21X (D) benzene rings, respectively. The dihedral angles between the benzene rings are A/B = 83.25 (15)°, A/C = 87.1 (2)°, A/D = 67.2 (2)°, B/C = 22.6 (2)° and B/D = 16.1 (2)°. The bond lengths and angles are comparable to those found in a related structure (Samshuddin et al., 2010). In the crystal, molecules are linked into a layer parallel to (100) through intermolecular C—H···π interactions (Table 1), involving Cg1 which is the centroid of the C10–C15 ring.
Experimental
A mixture of (2E)-3-(4-bromophenyl)-1-(4-fluorophenyl)prop-2-en-1-one (3.05 g, 0.01 mol) and phenyl hydrazine (0.98 ml, 0.01 mol) in 50 ml of glacial acetic acid was refluxed for 6 h. The reaction mixture was cooled and poured into 50 ml ice-cold water. The precipitate was collected by filtration and purified by recrystallization from toluene. Orange blocks were grown from ethanol by slow evaporation method (m.p. 397–399 K).
Refinement
All H atoms were positioned geometrically (C—H = 0.95, 0.99 and 1.00 Å) and refined using a riding model with Uiso(H) = 1.2Ueq(C). The fluoro-substituted benzene ring is statistically disordered over two conformations with a site-occupancy ratio of 0.516 (8):0.484 (8). Similarity (SAME), similar-ADP (SIMU) and FLAT restraints were used for the major and minor components of disordered fluoro-substituted benzene ring (C16–C21 and C16/C17X/C18X/C19/C20X/C21X). The highest peak is located at 0.31 Å from atom C17, whereas the deepest hole is located at 0.34 Å from atom C21.
Figures
Fig. 1.
Fig. 1.
The molecular structure of the title compound with atom labels with 50% probability displacement ellipsoids. The minor component of disorder is indicated by the open bonds.
Crystal data
C21H16BrFN2F(000) = 800
Mr = 395.27Dx = 1.547 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4161 reflections
a = 20.5345 (5) Åθ = 2.9–30.0°
b = 5.2689 (1) ŵ = 2.44 mm1
c = 16.1929 (5) ÅT = 100 K
β = 104.443 (2)°Block, orange
V = 1696.61 (7) Å30.25 × 0.13 × 0.09 mm
Z = 4
Data collection
Bruker SMART APEXII CCD area-detector diffractometer4974 independent reflections
Radiation source: fine-focus sealed tube3761 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
[var phi] and ω scansθmax = 30.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −29→28
Tmin = 0.583, Tmax = 0.818k = −7→7
16716 measured reflectionsl = −20→22
Refinement
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0403P)2 + 3.9007P] where P = (Fo2 + 2Fc2)/3
4974 reflections(Δ/σ)max = 0.001
263 parametersΔρmax = 1.26 e Å3
130 restraintsΔρmin = −0.99 e Å3
Special details
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)
xyzUiso*/UeqOcc. (<1)
Br10.438172 (16)0.29092 (7)0.31781 (2)0.02527 (11)
F11.03501 (11)1.0361 (5)0.31750 (17)0.0482 (7)
N10.76496 (13)0.5313 (5)0.52597 (18)0.0205 (6)
N20.82467 (12)0.5535 (5)0.50180 (17)0.0189 (5)
C10.58983 (16)0.7495 (6)0.4593 (2)0.0198 (6)
H1A0.59300.89420.49510.024*
C20.52691 (16)0.6511 (6)0.4199 (2)0.0210 (7)
H2A0.48720.72810.42820.025*
C30.52306 (15)0.4394 (6)0.3684 (2)0.0194 (6)
C40.58002 (16)0.3298 (6)0.3531 (2)0.0212 (6)
H4A0.57650.18660.31660.025*
C50.64254 (16)0.4316 (6)0.3919 (2)0.0202 (6)
H5A0.68190.35930.38080.024*
C60.64832 (15)0.6383 (6)0.4469 (2)0.0175 (6)
C70.71689 (15)0.7394 (6)0.4928 (2)0.0184 (6)
H7A0.71250.85230.54080.022*
C80.75404 (15)0.8818 (6)0.4346 (2)0.0193 (6)
H8A0.72920.86940.37400.023*
H8B0.76061.06300.45080.023*
C90.82035 (15)0.7440 (6)0.4509 (2)0.0183 (6)
C100.76131 (15)0.3686 (6)0.59269 (19)0.0171 (6)
C110.81265 (15)0.1909 (6)0.6237 (2)0.0202 (6)
H11A0.85150.18800.60200.024*
C120.80621 (16)0.0197 (6)0.6863 (2)0.0232 (7)
H12A0.8408−0.10140.70680.028*
C130.75020 (17)0.0222 (7)0.7196 (2)0.0237 (7)
H13A0.7461−0.09660.76210.028*
C140.70032 (16)0.2001 (7)0.6900 (2)0.0238 (7)
H14A0.66200.20380.71290.029*
C150.70535 (16)0.3739 (6)0.6272 (2)0.0213 (6)
H15A0.67080.49580.60780.026*
C160.87551 (16)0.8212 (6)0.4136 (2)0.0228 (7)
C190.98129 (18)0.9645 (7)0.3479 (2)0.0333 (8)
C170.8674 (3)0.9700 (12)0.3440 (4)0.0143 (13)0.516 (8)
H17A0.82321.02180.31530.017*0.516 (8)
C180.9209 (4)1.0507 (15)0.3126 (5)0.0138 (14)0.516 (8)
H18A0.91391.16640.26620.017*0.516 (8)
C200.9970 (4)0.8198 (14)0.4250 (5)0.0348 (17)0.516 (8)
H20A1.04200.77480.45260.042*0.516 (8)
C210.9429 (3)0.7482 (13)0.4575 (5)0.0287 (16)0.516 (8)
H21A0.95050.65130.50850.034*0.516 (8)
C17X0.8755 (4)1.0417 (15)0.3726 (4)0.0186 (15)0.484 (8)
H17B0.83871.15440.36840.022*0.484 (8)
C18X0.9274 (5)1.1126 (19)0.3360 (5)0.0211 (17)0.484 (8)
H18B0.92431.26360.30310.025*0.484 (8)
C20X0.9841 (3)0.7160 (14)0.3859 (4)0.0226 (14)0.484 (8)
H20B1.02100.60520.38780.027*0.484 (8)
C21X0.9309 (3)0.6444 (14)0.4195 (4)0.0200 (14)0.484 (8)
H21B0.93070.48340.44580.024*0.484 (8)
Atomic displacement parameters (Å2)
U11U22U33U12U13U23
Br10.01981 (15)0.03041 (18)0.02509 (18)−0.00327 (13)0.00464 (12)−0.00043 (15)
F10.0264 (11)0.0682 (17)0.0583 (16)0.0129 (11)0.0263 (11)0.0328 (14)
N10.0165 (12)0.0241 (14)0.0221 (14)0.0036 (10)0.0071 (11)0.0078 (11)
N20.0164 (11)0.0212 (14)0.0202 (14)0.0005 (10)0.0064 (10)0.0037 (11)
C10.0255 (15)0.0129 (16)0.0224 (15)0.0022 (11)0.0084 (13)−0.0011 (12)
C20.0204 (14)0.0199 (16)0.0258 (17)0.0022 (11)0.0114 (13)0.0010 (13)
C30.0180 (13)0.0225 (16)0.0182 (15)−0.0019 (11)0.0051 (12)0.0032 (13)
C40.0254 (15)0.0202 (17)0.0179 (15)0.0027 (12)0.0050 (12)−0.0005 (12)
C50.0201 (14)0.0223 (16)0.0182 (15)0.0072 (12)0.0050 (12)0.0003 (12)
C60.0192 (14)0.0164 (14)0.0174 (15)0.0020 (11)0.0057 (12)0.0026 (11)
C70.0182 (13)0.0170 (16)0.0198 (15)0.0027 (11)0.0043 (12)0.0004 (12)
C80.0207 (14)0.0174 (14)0.0209 (16)0.0019 (11)0.0073 (12)0.0021 (12)
C90.0192 (13)0.0164 (16)0.0193 (15)0.0014 (11)0.0048 (12)0.0010 (12)
C100.0183 (13)0.0182 (14)0.0132 (14)−0.0042 (11)0.0008 (11)0.0002 (11)
C110.0168 (13)0.0219 (15)0.0203 (15)−0.0022 (12)0.0017 (12)0.0010 (13)
C120.0214 (15)0.0212 (16)0.0233 (17)−0.0021 (12)−0.0015 (13)0.0038 (13)
C130.0279 (16)0.0258 (17)0.0165 (16)−0.0049 (13)0.0039 (13)0.0062 (13)
C140.0247 (15)0.0282 (17)0.0197 (16)−0.0057 (13)0.0082 (13)0.0009 (14)
C150.0218 (14)0.0231 (16)0.0193 (16)0.0006 (12)0.0055 (13)0.0012 (13)
C160.0207 (14)0.0230 (16)0.0251 (16)0.0023 (12)0.0066 (12)0.0045 (13)
C190.0246 (16)0.042 (2)0.038 (2)0.0051 (15)0.0157 (15)0.0160 (17)
C170.011 (2)0.022 (3)0.007 (3)−0.002 (2)−0.004 (2)0.002 (2)
C180.015 (3)0.020 (4)0.005 (3)−0.004 (2)0.000 (3)−0.001 (2)
C200.023 (3)0.041 (4)0.040 (4)0.003 (3)0.005 (3)0.014 (3)
C210.026 (3)0.033 (4)0.028 (3)0.003 (3)0.006 (3)0.012 (3)
C17X0.018 (3)0.018 (3)0.019 (4)0.001 (3)0.004 (3)0.000 (3)
C18X0.026 (3)0.022 (4)0.013 (4)−0.004 (3)0.001 (3)0.000 (3)
C20X0.022 (3)0.026 (3)0.020 (3)0.001 (3)0.006 (2)−0.005 (3)
C21X0.027 (3)0.020 (3)0.014 (3)−0.001 (2)0.005 (2)−0.005 (2)
Geometric parameters (Å, º)
Br1—C31.900 (3)C12—C131.386 (5)
F1—C191.368 (4)C12—H12A0.9500
N1—N21.382 (3)C13—C141.383 (5)
N1—C101.395 (4)C13—H13A0.9500
N1—C71.484 (4)C14—C151.391 (5)
N2—C91.288 (4)C14—H14A0.9500
C1—C21.391 (5)C15—H15A0.9500
C1—C61.395 (4)C16—C17X1.338 (9)
C1—H1A0.9500C16—C171.349 (8)
C2—C31.383 (5)C16—C211.441 (7)
C2—H2A0.9500C16—C21X1.454 (7)
C3—C41.381 (4)C19—C181.310 (9)
C4—C51.389 (4)C19—C18X1.328 (11)
C4—H4A0.9500C19—C201.429 (8)
C5—C61.393 (4)C19—C20X1.442 (8)
C5—H5A0.9500C17—C181.389 (9)
C6—C71.516 (4)C17—H17A0.9500
C7—C81.546 (4)C18—H18A0.9500
C7—H7A1.0000C20—C211.395 (9)
C8—C91.507 (4)C20—H20A0.9500
C8—H8A0.9900C21—H21A0.9500
C8—H8B0.9900C17X—C18X1.394 (10)
C9—C161.467 (4)C17X—H17B0.9500
C10—C151.398 (4)C18X—H18B0.9500
C10—C111.406 (4)C20X—C21X1.389 (9)
C11—C121.388 (5)C20X—H20B0.9500
C11—H11A0.9500C21X—H21B0.9500
N2—N1—C10119.6 (2)C12—C13—H13A120.4
N2—N1—C7113.1 (2)C13—C14—C15121.1 (3)
C10—N1—C7125.1 (3)C13—C14—H14A119.5
C9—N2—N1108.8 (2)C15—C14—H14A119.5
C2—C1—C6120.8 (3)C14—C15—C10119.8 (3)
C2—C1—H1A119.6C14—C15—H15A120.1
C6—C1—H1A119.6C10—C15—H15A120.1
C3—C2—C1118.9 (3)C17X—C16—C21110.9 (4)
C3—C2—H2A120.5C17—C16—C21118.1 (5)
C1—C2—H2A120.5C17X—C16—C21X119.5 (5)
C4—C3—C2121.5 (3)C17—C16—C21X111.1 (4)
C4—C3—Br1118.5 (2)C17X—C16—C9122.7 (4)
C2—C3—Br1120.0 (2)C17—C16—C9123.9 (4)
C3—C4—C5119.1 (3)C21—C16—C9117.9 (4)
C3—C4—H4A120.5C21X—C16—C9117.8 (4)
C5—C4—H4A120.5C18—C19—F1120.5 (5)
C4—C5—C6120.9 (3)C18X—C19—F1120.2 (5)
C4—C5—H5A119.6C18—C19—C20123.3 (5)
C6—C5—H5A119.6C18X—C19—C20116.0 (5)
C5—C6—C1118.8 (3)F1—C19—C20115.8 (4)
C5—C6—C7120.6 (3)C18—C19—C20X115.7 (5)
C1—C6—C7120.6 (3)C18X—C19—C20X122.6 (6)
N1—C7—C6111.7 (2)F1—C19—C20X117.0 (4)
N1—C7—C8101.2 (2)C16—C17—C18122.7 (6)
C6—C7—C8114.3 (3)C16—C17—H17A118.7
N1—C7—H7A109.8C18—C17—H17A118.7
C6—C7—H7A109.8C19—C18—C17118.9 (7)
C8—C7—H7A109.8C19—C18—H18A120.6
C9—C8—C7102.8 (2)C17—C18—H18A120.6
C9—C8—H8A111.2C21—C20—C19116.5 (6)
C7—C8—H8A111.2C21—C20—H20A121.7
C9—C8—H8B111.2C19—C20—H20A121.7
C7—C8—H8B111.2C20—C21—C16119.9 (6)
H8A—C8—H8B109.1C20—C21—H21A120.0
N2—C9—C16122.8 (3)C16—C21—H21A120.0
N2—C9—C8113.7 (3)C16—C17X—C18X122.6 (7)
C16—C9—C8123.4 (3)C16—C17X—H17B118.7
N1—C10—C15120.4 (3)C18X—C17X—H17B118.7
N1—C10—C11120.4 (3)C19—C18X—C17X118.6 (8)
C15—C10—C11119.2 (3)C19—C18X—H18B120.7
C12—C11—C10119.7 (3)C17X—C18X—H18B120.7
C12—C11—H11A120.2C21X—C20X—C19117.5 (6)
C10—C11—H11A120.2C21X—C20X—H20B121.2
C13—C12—C11121.1 (3)C19—C20X—H20B121.2
C13—C12—H12A119.4C20X—C21X—C16118.6 (6)
C11—C12—H12A119.4C20X—C21X—H21B120.7
C14—C13—C12119.1 (3)C16—C21X—H21B120.7
C14—C13—H13A120.4
C10—N1—N2—C9−168.5 (3)C8—C9—C16—C17−19.9 (5)
C7—N1—N2—C9−4.5 (4)N2—C9—C16—C21−23.3 (5)
C6—C1—C2—C30.4 (5)C8—C9—C16—C21155.5 (4)
C1—C2—C3—C4−2.2 (5)N2—C9—C16—C21X13.7 (5)
C1—C2—C3—Br1177.1 (2)C8—C9—C16—C21X−167.4 (4)
C2—C3—C4—C51.4 (5)C17X—C16—C17—C1880.8 (12)
Br1—C3—C4—C5−177.9 (2)C21—C16—C17—C181.2 (4)
C3—C4—C5—C61.3 (5)C21X—C16—C17—C18−33.9 (4)
C4—C5—C6—C1−3.0 (5)C9—C16—C17—C18176.7 (4)
C4—C5—C6—C7176.6 (3)C18X—C19—C18—C17−85.6 (19)
C2—C1—C6—C52.2 (5)F1—C19—C18—C17178.7 (4)
C2—C1—C6—C7−177.5 (3)C20—C19—C18—C17−9.2 (6)
N2—N1—C7—C6128.1 (3)C20X—C19—C18—C1728.6 (6)
C10—N1—C7—C6−69.1 (4)C16—C17—C18—C195.1 (6)
N2—N1—C7—C86.1 (3)C18—C19—C20—C216.8 (6)
C10—N1—C7—C8168.9 (3)C18X—C19—C20—C2130.2 (7)
C5—C6—C7—N1−42.2 (4)F1—C19—C20—C21179.2 (5)
C1—C6—C7—N1137.4 (3)C20X—C19—C20—C21−80.2 (8)
C5—C6—C7—C871.9 (4)C19—C20—C21—C16−0.2 (7)
C1—C6—C7—C8−108.4 (3)C17X—C16—C21—C20−30.3 (6)
N1—C7—C8—C9−5.0 (3)C17—C16—C21—C20−3.5 (6)
C6—C7—C8—C9−125.3 (3)C21X—C16—C21—C2082.0 (8)
N1—N2—C9—C16179.7 (3)C9—C16—C21—C20−179.3 (4)
N1—N2—C9—C80.7 (4)C17—C16—C17X—C18X−77.7 (12)
C7—C8—C9—N23.0 (4)C21—C16—C17X—C18X34.0 (5)
C7—C8—C9—C16−175.9 (3)C21X—C16—C17X—C18X−1.0 (4)
N2—N1—C10—C15169.6 (3)C9—C16—C17X—C18X−178.8 (4)
C7—N1—C10—C157.7 (5)C18—C19—C18X—C17X87.1 (19)
N2—N1—C10—C11−12.9 (4)F1—C19—C18X—C17X−175.8 (4)
C7—N1—C10—C11−174.7 (3)C20—C19—C18X—C17X−28.3 (6)
N1—C10—C11—C12−175.9 (3)C20X—C19—C18X—C17X9.7 (6)
C15—C10—C11—C121.7 (5)C16—C17X—C18X—C19−5.4 (6)
C10—C11—C12—C13−0.7 (5)C18—C19—C20X—C21X−30.8 (6)
C11—C12—C13—C14−0.5 (5)C18X—C19—C20X—C21X−7.4 (6)
C12—C13—C14—C150.6 (5)F1—C19—C20X—C21X177.9 (4)
C13—C14—C15—C100.5 (5)C20—C19—C20X—C21X81.3 (8)
N1—C10—C15—C14176.0 (3)C19—C20X—C21X—C160.8 (6)
C11—C10—C15—C14−1.6 (5)C17X—C16—C21X—C20X3.1 (5)
N2—C9—C16—C17X−168.4 (4)C17—C16—C21X—C20X29.6 (5)
C8—C9—C16—C17X10.4 (5)C21—C16—C21X—C20X−79.9 (8)
N2—C9—C16—C17161.2 (4)C9—C16—C21X—C20X−178.9 (4)
Hydrogen-bond geometry (Å, º)
Cg1 is the centroid of the C10–C15 ring.
D—H···AD—HH···AD···AD—H···A
C7—H7A···Cg1i1.002.603.522 (3)153
C17—H17A···Cg1ii0.952.993.752 (6)138
Symmetry codes: (i) x, y+1, z; (ii) x, −y+1/2, z−3/2.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5174).
References
  • Bruker (2009). SADABS, APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.
  • Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010). Acta Cryst. E66, o582–o583. [PMC free article] [PubMed]
  • Samshuddin, S., Narayana, B., Baktir, Z., Akkurt, M. & Yathirajan, H. S. (2011). Der Pharma Chem. 3, 487–493.
  • Samshuddin, S., Narayana, B., Yathirajan, H. S., Safwan, A. P. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1279–o1280. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of
International Union of Crystallography