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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 9| September 2011| Pages o2537-o2538
doi:10.1107/S1600536811034969

2-Chloro-N-[2-(2-fluoro­benzo­yl)-4-nitro­phen­yl]-N-methyl­acetamide

B. P. Siddaraju,a Jerry P. Jasinski,b* James A. Golen,b H. S. Yathirajana and C. R. Rajuc

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and cDepartment of Chemistry, PES College of Science, Mandya 571 401, India
*Correspondence e-mail: jjasinski@keene.edu

(Received 16 August 2011; accepted 25 August 2011; online 31 August 2011)

The title compound, C16H12ClFN2O4, crystallizes with two mol­ecules in the asymmetric unit in which the dihedral angles between the mean planes of the two benzene rings are 65.1 (7) and 65.6 (6)°. In each mol­ecule, the nitro group displays rotational disorder over two orientations in a 0.503 (11):0.497 (11) ratio and the Cl atom is disordered in a 0.432 (5):0.568 (5) ratio. In one mol­ecule, the F atoms is statistically disordered over two positions. The crystal packing features weak inter­molecular C—H⋯O and C—H⋯Cl inter­actions, which form a layered network.

Related literature

For anti-anaphylactic and disease-related agents, see: Evans et al. (1987[Evans, D., Cracknell, M. E., Saunders, J. C., Smith, C. E., Willamson, W. R. N., Dowson, W. & Sweatman, W. J. F. (1987). J. Med. Chem. 30, 1321-1327.]). For an inter­mediate in the synthesis of flunitra­zepam (systematic name: 6-(2-fluoro­phen­yl)-2-methyl-9-nitro-2,5-diaza­bicyclo­[5.4.0]undeca-5,8,10,12-tetraen-3-one), see: Malanciuc et al. (2009[Malanciuc, C., Arama, C., Saramet, I., Monciu, C. M., Nedelcu, A. & Constantinescu, C. (2009). Farmacia, 57, 167-183.]). For related structures, see: Dutkiewicz et al. (2010[Dutkiewicz, G., Siddaraju, B. P., Yathirajan, H. S., Narayana, B. & Kubicki, M. (2010). Acta Cryst. E66, o499.]); Jasinski et al. (2009[Jasinski, J. P., Butcher, R. J., Hakim Al-Arique, Q. N. M., Yathirajan, H. S. & Ramesha, A. R. (2009). Acta Cryst. E65, o1908-o1909.]); Khan et al. (2010[Khan, F. N., Roopan, S. M., Malathi, N., Hathwar, V. R. & Akkurt, M. (2010). Acta Cryst. E66, o1434.]); Malathy Sony et al. (2005a[Malathy Sony, S. M., Charles, P., Ponnuswamy, M. N. & Nethaji, M. (2005a). Acta Cryst. E61, o632-o634.],b[Malathy Sony, S. M., Charles, P., Ponnuswamy, M. N. & Nethaji, M. (2005b). Acta Cryst. E61, o801-o803.]); Prasanna & Guru Row (2000[Prasanna, M. D. & Guru Row, T. N. (2000). CrystEngComm, 2, 134-140.]). For standard bond lengths, see Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C16H12ClFN2O4

  • Mr = 350.73

  • Triclinic, [P \overline 1]

  • a = 8.1339 (6) Å

  • b = 10.9639 (8) Å

  • c = 17.8690 (11) Å

  • α = 81.251 (6)°

  • β = 82.239 (6)°

  • γ = 87.937 (6)°

  • V = 1560.38 (19) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.28 mm−1

  • T = 200 K

  • 0.24 × 0.16 × 0.12 mm
Data collection

  • Oxford Diffraction Xcalibur Eos Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.936, Tmax = 0.967

  • 13030 measured reflections

  • 6373 independent reflections

  • 3774 reflections with I > 2σ(I)

  • Rint = 0.041
Refinement

  • R[F2 > 2σ(F2)] = 0.066

  • wR(F2) = 0.172

  • S = 1.03

  • 6373 reflections

  • 448 parameters

  • 16 restraints

  • H-atom parameters constrained

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C32—H32A⋯O1 0.98 2.48 3.383 (4) 154
C29—H29⋯O5i 0.95 2.50 3.194 (5) 130
C28—H28⋯Cl1Aii 0.95 2.74 3.543 (6) 143
C17—H17A⋯O1 0.99 2.38 3.348 (4) 165
C16—H16B⋯O2iii 0.98 2.47 3.45 (1) 176
C7—H7⋯O7iv 0.95 2.37 3.31 (2) 173
Symmetry codes: (i) x+1, y, z; (ii) -x+2, -y, -z+1; (iii) -x+1, -y+1, -z; (iv) -x+1, -y, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811034969/im2312sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811034969/im2312Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811034969/im2312Isup3.cml

checkCIF report


Comment top

Benzophenone and related compounds have been reported to act as antiallergic, anti-inflammatory, antiasthmatic, antimalarial, antimicrobial and antianaphylactic agents (Evans et al., 1987). The title compound is an intermediate in the synthesis of certain anxiolytic, anticonvulsant and sedative drugs and is also used as an intermediate to synthesize flunitrazepam, which is used as a potent hypnotic and powerful sedative, anticonvulsant, anxiolytic, amnestic, and skeletal muscle relaxant drug (Malanciuc et al., 2009). The crystal structures of 2-chloroacetamido-5-chloro-2'-fluorobenzophenone (Prasanna & Guru Row, 2000), N-(2-benzoyl-4-chlorophenyl)-2- chloroacetamide (Malathy Sony et al., 2005a), 2-methoxy-5-methylphenyl phenyl ketone (Malathy Sony et al., 2005b), 2-amino-5-nitrophenyl 2-chlorophenyl ketone (Jasinski et al., 2009), N-[4-chloro-2-(2-chlorobenzoyl)phenyl]acetamide (Khan et al., 2010) and 2-chloro-N-[4-chloro-2-(2-chlorobenzoyl)phenyl]acetamide (Dutkiewicz et al., 2010) have been reported. In view of the importance of the title compound, C16H12N2O4ClF, the crystal structure of (I) is reported.

The title compound, C16H12N2O4ClF, crystallizes with two molecules in the asymmetric unit (Fig. 1). The dihedral angle between the mean planes of the two benzene rings is 65.1 (7)° and 65.6 (6)°, respectively. Bond lengths are in normal ranges (Allen et al., 1987). The two nitro groups display rotational disorder over two positions in a ratio of 0.503 (11) : 0.497 (11). In addition, disorder is observed concerning both chlorine atoms in a ratio of 0.432 (5) : 0.568 (5). One of the fluorine atoms (F2) is statistically disordered (0.50 (0)) over two positions (F2 and F2A). The crystal packing is realized by weak intermolecular C—H···O and C—H···Cl interactions forming a supermolecular 2-D network (Fig. 2).

Related literature top

For anti-anaphylactic and disease-related agents, see: Evans et al. (1987). For an intermediate in the synthesis of the sedative, anticonvulsant, anxiolytic, amnestic and skeletal muscle relaxant drug flunitrazepam (bsystematic name: 6-(2-fluorophenyl)-2-methyl-9-nitro-2,5-diazabicyclo[5.4.0]undeca-5,8,10,12-tetraen-3-one), see: Malanciuc et al. (2009). For related structures, see: Dutkiewicz et al. (2010); Jasinski et al. (2009); Khan et al. (2010); Malathy Sony et al. (2005a,b); Prasanna & Guru Row (2000). For standard bond lengths, see Allen et al. (1987).

Experimental top

The title compound was obtained as a gift sample from R.L. Fine Chem., Bangalore, India. The compound was recrystallized from acetone (m.p.: 387–389 K).

Refinement top

The two nitro groups are rotationally disordered over two positions [O2 & O3 (0.503 (11), O2A & O3A (0.497 (11)) and O6 & O7 (0.503 (11), O6A & O7A (0.497 (11)]. In addition, disorder is observed concerning Cl1 & Cl2 (0.432 (5)) and Cl1A & Cl2A (0.568 (5)). Moreover, F2 and F2A are disordered (0.50 (0)) over two positions. All H atoms were placed in their calculated positions and then refined using the riding model with C–H lengths of 0.95 Å (CH), 0.99 Å (CH2) or 0.98 Å (CH3). The isotropic displacement parameters for these atoms were set to 1.19–1.20 (CH, CH2) or 1.50 (CH3) times Ueq of the parent atom.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title molecule showing two molecules in the asymmetric unit, displacement ellipsoids are depicted on the 30% probability level. Dashed lines represent disordered atoms.
[Figure 2] Fig. 2. Packing diagram of the title compound viewed down the b axis. Dashed lines indicate weak intermolecular C—H···O and C—H···Cl interactions.
2-Chloro-N-[2-(2-fluorobenzoyl)-4-nitrophenyl]-N- methylacetamide top
Crystal data top
C16H12ClFN2O4Z = 4
Mr = 350.73F(000) = 720
Triclinic, P1Dx = 1.493 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.1339 (6) ÅCell parameters from 2929 reflections
b = 10.9639 (8) Åθ = 3.1–32.4°
c = 17.8690 (11) ŵ = 0.28 mm−1
α = 81.251 (6)°T = 200 K
β = 82.239 (6)°Block, colorless
γ = 87.937 (6)°0.24 × 0.16 × 0.12 mm
V = 1560.38 (19) Å3
Data collection top
Oxford Diffraction Xcalibur Eos Gemini
diffractometer		6373 independent reflections
Radiation source: Enhance (Mo) X-ray Source3774 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
Detector resolution: 16.1500 pixels mm-1θmax = 26.4°, θmin = 3.1°
ω scansh = −10→10
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2010)		k = −12→13
Tmin = 0.936, Tmax = 0.967l = −22→21
13030 measured reflections
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0665P)2 + 0.3335P]
where P = (Fo2 + 2Fc2)/3
6373 reflections(Δ/σ)max = 0.012
448 parametersΔρmax = 0.32 e Å−3
16 restraintsΔρmin = −0.36 e Å−3
Crystal data top
C16H12ClFN2O4γ = 87.937 (6)°
Mr = 350.73V = 1560.38 (19) Å3
Triclinic, P1Z = 4
a = 8.1339 (6) ÅMo Kα radiation
b = 10.9639 (8) ŵ = 0.28 mm−1
c = 17.8690 (11) ÅT = 200 K
α = 81.251 (6)°0.24 × 0.16 × 0.12 mm
β = 82.239 (6)°
Data collection top
Oxford Diffraction Xcalibur Eos Gemini
diffractometer		6373 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2010)		3774 reflections with I > 2σ(I)
Tmin = 0.936, Tmax = 0.967Rint = 0.041
13030 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06616 restraints
wR(F2) = 0.172H-atom parameters constrained
S = 1.03Δρmax = 0.32 e Å−3
6373 reflectionsΔρmin = −0.36 e Å−3
448 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*/UeqOcc. (<1)
C10.6305 (4)0.5284 (3)0.37754 (17)0.0528 (9)
H1A0.50920.52220.39300.063*
H1B0.65540.61700.36180.063*
C20.6740 (4)0.4643 (3)0.30868 (17)0.0397 (7)
C30.6349 (4)0.4613 (2)0.17778 (16)0.0357 (7)
C40.7948 (4)0.4601 (3)0.13956 (18)0.0409 (7)
H40.88380.48890.16120.049*
C50.8253 (4)0.4175 (3)0.07052 (18)0.0447 (8)
H50.93520.41420.04490.054*
C60.6941 (4)0.3797 (3)0.03924 (17)0.0444 (8)
C70.5340 (4)0.3788 (3)0.07590 (17)0.0431 (8)
H70.44550.35250.05290.052*
C80.5044 (4)0.4168 (3)0.14665 (17)0.0379 (7)
C90.3307 (4)0.4051 (3)0.18774 (19)0.0448 (8)
C100.3030 (4)0.3575 (3)0.27043 (19)0.0434 (8)
C110.3959 (4)0.2618 (3)0.3054 (2)0.0508 (9)
C120.3721 (5)0.2190 (4)0.3814 (2)0.0683 (11)
H120.43740.15260.40300.082*
C130.2500 (6)0.2752 (4)0.4261 (2)0.0799 (13)
H130.23260.24860.47970.096*
C140.1531 (5)0.3689 (4)0.3946 (3)0.0760 (13)
H140.06920.40650.42630.091*
C150.1775 (4)0.4089 (4)0.3168 (2)0.0598 (10)
H150.10780.47200.29500.072*
C160.5018 (4)0.6286 (3)0.24344 (19)0.0491 (8)
H16A0.40590.61840.28330.074*
H16B0.46330.64810.19330.074*
H16C0.57020.69610.25160.074*
C170.8713 (5)0.0822 (3)0.37310 (19)0.0630 (10)
H17A0.82360.16650.36290.076*
H17B0.99340.09000.36820.076*
C180.8310 (4)0.0101 (3)0.31241 (19)0.0455 (8)
C190.8622 (4)−0.0031 (3)0.17869 (17)0.0411 (7)
C200.7930 (5)0.0703 (3)0.1207 (2)0.0652 (10)
H200.77350.15550.12370.078*
C210.7519 (6)0.0231 (4)0.0590 (2)0.0734 (12)
H210.70640.07450.01890.088*
C220.7787 (4)−0.1018 (3)0.05717 (19)0.0540 (9)
C230.8398 (4)−0.1771 (3)0.11459 (18)0.0435 (8)
H230.8512−0.26310.11270.052*
C240.8858 (4)−0.1294 (3)0.17617 (17)0.0378 (7)
C250.9562 (4)−0.2199 (3)0.23510 (17)0.0388 (7)
C261.0948 (4)−0.1857 (3)0.27359 (18)0.0399 (7)
C271.1021 (4)−0.2291 (3)0.3501 (2)0.0531 (9)
H311.0170−0.28140.37780.064*0.50
C281.2290 (6)−0.1986 (4)0.3868 (2)0.0709 (11)
H281.2299−0.22810.43960.085*
C291.3531 (5)−0.1262 (4)0.3474 (3)0.0747 (13)
H291.4411−0.10530.37290.090*
C301.3528 (4)−0.0830 (3)0.2716 (3)0.0655 (11)
H301.4407−0.03360.24370.079*
C321.0045 (5)0.1643 (3)0.2218 (2)0.0575 (10)
H32A0.93430.23710.22940.086*
H32B1.05550.17220.16840.086*
H32C1.09160.15780.25520.086*
N10.6014 (3)0.5132 (2)0.24675 (13)0.0349 (6)
N20.7239 (4)0.3326 (3)−0.03396 (17)0.0622 (9)
N30.9025 (3)0.0527 (2)0.24041 (14)0.0408 (6)
N40.7393 (4)−0.1532 (4)−0.00907 (19)0.0699 (9)
O10.7643 (3)0.3733 (2)0.30914 (13)0.0539 (6)
O20.6212 (9)0.2889 (10)−0.0650 (6)0.0682 (10)0.503 (11)
O30.8746 (8)0.3465 (9)−0.0608 (4)0.0682 (10)0.503 (11)
O2A0.5898 (8)0.3148 (10)−0.0579 (6)0.0682 (10)0.497 (11)
O3A0.8581 (8)0.3038 (9)−0.0666 (5)0.0682 (10)0.497 (11)
O40.2145 (3)0.4335 (3)0.15219 (15)0.0671 (7)
O50.7432 (3)−0.0798 (2)0.32668 (13)0.0598 (7)
O60.6964 (13)−0.0882 (7)−0.0642 (5)0.0802 (18)0.503 (11)
O70.775 (2)−0.2652 (7)−0.0057 (5)0.0802 (18)0.503 (11)
O6A0.6291 (12)−0.0950 (8)−0.0452 (5)0.0802 (18)0.497 (11)
O7A0.7985 (19)−0.2503 (8)−0.0264 (6)0.0802 (18)0.497 (11)
O80.9024 (3)−0.32484 (19)0.24960 (14)0.0583 (7)
F10.5148 (2)0.20503 (17)0.26090 (12)0.0662 (6)
F20.9848 (4)−0.3000 (3)0.39096 (18)0.0501 (9)0.50
F2A1.2279 (7)−0.0727 (5)0.1659 (4)0.1118 (19)0.50
Cl10.7252 (8)0.4779 (4)0.45561 (19)0.0750 (4)0.432 (5)
Cl20.8013 (6)0.0204 (5)0.46559 (17)0.0750 (4)0.432 (5)
Cl1A0.7034 (6)0.4317 (3)0.45940 (14)0.0750 (4)0.568 (5)
Cl2A0.7300 (5)0.0317 (4)0.45918 (13)0.0750 (4)0.568 (5)
C311.2222 (4)−0.1128 (3)0.2367 (2)0.0509 (9)
H31A1.2206−0.08100.18430.061*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.053 (2)0.063 (2)0.0410 (18)0.0030 (17)−0.0029 (16)−0.0080 (16)
C20.0333 (17)0.0402 (18)0.0450 (18)−0.0049 (14)−0.0034 (14)−0.0045 (14)
C30.0358 (16)0.0265 (15)0.0444 (17)0.0022 (12)−0.0076 (14)−0.0023 (13)
C40.0337 (17)0.0350 (17)0.0520 (19)−0.0020 (13)−0.0042 (14)−0.0010 (14)
C50.0420 (18)0.0380 (17)0.0484 (19)0.0056 (14)0.0035 (15)0.0015 (15)
C60.054 (2)0.0348 (17)0.0411 (17)0.0102 (14)−0.0026 (16)−0.0008 (14)
C70.051 (2)0.0329 (17)0.0482 (18)0.0036 (14)−0.0151 (16)−0.0074 (14)
C80.0362 (17)0.0332 (16)0.0460 (17)0.0030 (12)−0.0099 (14)−0.0080 (13)
C90.0365 (18)0.0419 (18)0.060 (2)0.0009 (14)−0.0116 (16)−0.0168 (16)
C100.0318 (17)0.0420 (18)0.058 (2)−0.0080 (14)−0.0018 (15)−0.0150 (15)
C110.043 (2)0.0416 (19)0.066 (2)−0.0086 (15)0.0026 (17)−0.0086 (17)
C120.071 (3)0.058 (2)0.068 (3)−0.008 (2)0.001 (2)0.009 (2)
C130.083 (3)0.085 (3)0.064 (3)−0.021 (3)0.014 (3)−0.004 (2)
C140.061 (3)0.087 (3)0.076 (3)−0.003 (2)0.017 (2)−0.022 (3)
C150.040 (2)0.068 (2)0.072 (3)−0.0051 (17)0.0019 (18)−0.017 (2)
C160.050 (2)0.0418 (19)0.058 (2)0.0097 (15)−0.0119 (17)−0.0141 (16)
C170.080 (3)0.053 (2)0.060 (2)0.0080 (19)−0.011 (2)−0.0182 (18)
C180.0444 (19)0.0406 (19)0.052 (2)0.0103 (15)−0.0063 (16)−0.0103 (15)
C190.0424 (18)0.0344 (17)0.0465 (18)−0.0006 (13)−0.0052 (15)−0.0070 (14)
C200.093 (3)0.0361 (19)0.071 (2)0.0108 (18)−0.032 (2)−0.0048 (18)
C210.107 (3)0.053 (2)0.065 (2)0.007 (2)−0.042 (2)0.001 (2)
C220.061 (2)0.054 (2)0.050 (2)−0.0052 (17)−0.0132 (18)−0.0119 (17)
C230.0443 (18)0.0379 (17)0.0496 (19)−0.0034 (14)−0.0060 (15)−0.0104 (15)
C240.0353 (16)0.0313 (16)0.0463 (17)−0.0012 (12)−0.0038 (14)−0.0057 (13)
C250.0376 (17)0.0305 (16)0.0481 (18)−0.0015 (13)−0.0031 (14)−0.0069 (13)
C260.0368 (17)0.0294 (16)0.0551 (19)0.0012 (13)−0.0084 (15)−0.0099 (14)
C270.058 (2)0.048 (2)0.057 (2)0.0092 (17)−0.0190 (18)−0.0144 (17)
C280.084 (3)0.067 (3)0.072 (3)0.020 (2)−0.036 (2)−0.024 (2)
C290.057 (3)0.070 (3)0.115 (4)0.014 (2)−0.039 (3)−0.049 (3)
C300.040 (2)0.052 (2)0.110 (4)−0.0059 (17)−0.006 (2)−0.031 (2)
C320.070 (2)0.0360 (18)0.067 (2)−0.0078 (16)−0.0020 (19)−0.0130 (16)
N10.0324 (13)0.0309 (13)0.0445 (14)0.0010 (10)−0.0107 (11)−0.0106 (11)
N20.084 (2)0.0527 (19)0.0444 (18)0.0192 (17)0.0021 (17)−0.0048 (14)
N30.0432 (15)0.0307 (13)0.0497 (15)−0.0001 (11)−0.0049 (12)−0.0106 (11)
N40.074 (2)0.081 (3)0.061 (2)−0.0025 (19)−0.0255 (18)−0.0142 (19)
O10.0547 (14)0.0482 (14)0.0569 (14)0.0132 (11)−0.0104 (12)−0.0023 (11)
O20.0908 (18)0.065 (4)0.0550 (16)0.0240 (17)−0.0022 (13)−0.0412 (18)
O30.0908 (18)0.065 (4)0.0550 (16)0.0240 (17)−0.0022 (13)−0.0412 (18)
O2A0.0908 (18)0.065 (4)0.0550 (16)0.0240 (17)−0.0022 (13)−0.0412 (18)
O3A0.0908 (18)0.065 (4)0.0550 (16)0.0240 (17)−0.0022 (13)−0.0412 (18)
O40.0392 (14)0.091 (2)0.0759 (17)0.0017 (13)−0.0212 (13)−0.0155 (15)
O50.0565 (15)0.0591 (15)0.0610 (15)−0.0140 (12)0.0073 (12)−0.0096 (12)
O60.088 (4)0.103 (2)0.057 (3)0.002 (3)−0.022 (3)−0.026 (2)
O70.088 (4)0.103 (2)0.057 (3)0.002 (3)−0.022 (3)−0.026 (2)
O6A0.088 (4)0.103 (2)0.057 (3)0.002 (3)−0.022 (3)−0.026 (2)
O7A0.088 (4)0.103 (2)0.057 (3)0.002 (3)−0.022 (3)−0.026 (2)
O80.0678 (16)0.0332 (12)0.0758 (16)−0.0164 (11)−0.0232 (13)0.0017 (11)
F10.0638 (13)0.0448 (11)0.0829 (15)0.0077 (9)0.0073 (11)−0.0042 (10)
F20.056 (2)0.055 (2)0.0343 (18)−0.0175 (18)−0.0003 (17)0.0099 (16)
F2A0.095 (4)0.092 (4)0.139 (5)−0.020 (3)0.016 (4)−0.012 (4)
Cl10.0919 (13)0.0855 (10)0.0464 (5)0.0205 (15)−0.0146 (5)−0.0069 (6)
Cl20.0919 (13)0.0855 (10)0.0464 (5)0.0205 (15)−0.0146 (5)−0.0069 (6)
Cl1A0.0919 (13)0.0855 (10)0.0464 (5)0.0205 (15)−0.0146 (5)−0.0069 (6)
Cl2A0.0919 (13)0.0855 (10)0.0464 (5)0.0205 (15)−0.0146 (5)−0.0069 (6)
C310.049 (2)0.0389 (19)0.061 (2)−0.0036 (15)0.0027 (18)−0.0052 (17)
Geometric parameters (Å, º) top
C1—C21.503 (4)C17—H17B0.9900
C1—Cl11.694 (6)C18—O51.213 (4)
C1—Cl1A1.825 (5)C18—N31.359 (4)
C1—H1A0.9900C19—C201.382 (5)
C1—H1B0.9900C19—C241.398 (4)
C2—O11.217 (4)C19—N31.420 (4)
C2—N11.354 (4)C20—C211.371 (5)
C3—C41.385 (4)C20—H200.9500
C3—C81.398 (4)C21—C221.383 (5)
C3—N11.424 (4)C21—H210.9500
C4—C51.373 (4)C22—C231.353 (5)
C4—H40.9500C22—N41.463 (5)
C5—C61.374 (5)C23—C241.387 (4)
C5—H50.9500C23—H230.9500
C6—C71.376 (4)C24—C251.491 (4)
C6—N21.465 (4)C25—O81.224 (3)
C7—C81.378 (4)C25—C261.484 (4)
C7—H70.9500C26—C311.365 (4)
C8—C91.502 (4)C26—C271.386 (4)
C9—O41.214 (4)C27—C281.372 (5)
C9—C101.480 (5)C27—H310.9500
C10—C151.385 (4)C28—C291.357 (6)
C10—C111.390 (5)C28—H280.9500
C11—C121.359 (5)C29—C301.366 (6)
C11—F11.361 (4)C29—H290.9500
C12—C131.377 (6)C30—C311.375 (5)
C12—H120.9500C30—H300.9500
C13—C141.370 (6)C32—N31.473 (4)
C13—H130.9500C32—H32A0.9800
C14—C151.383 (5)C32—H32B0.9800
C14—H140.9500C32—H32C0.9800
C15—H150.9500N2—O21.212 (7)
C16—N11.476 (4)N2—O3A1.221 (6)
C16—H16A0.9800N2—O2A1.256 (7)
C16—H16B0.9800N2—O31.260 (6)
C16—H16C0.9800N4—O61.208 (7)
C17—C181.512 (5)N4—O7A1.218 (7)
C17—Cl21.717 (5)N4—O71.245 (7)
C17—Cl2A1.817 (4)N4—O6A1.272 (6)
C17—H17A0.9900C31—H31A0.9500
C2—C1—Cl1117.8 (3)N3—C18—C17114.8 (3)
C2—C1—Cl1A108.3 (3)C20—C19—C24119.6 (3)
C2—C1—H1A107.9C20—C19—N3118.2 (3)
Cl1—C1—H1A107.9C24—C19—N3122.2 (3)
Cl1A—C1—H1A99.7C21—C20—C19121.5 (3)
C2—C1—H1B107.9C21—C20—H20119.2
Cl1—C1—H1B107.9C19—C20—H20119.2
Cl1A—C1—H1B124.8C20—C21—C22117.9 (4)
H1A—C1—H1B107.2C20—C21—H21121.1
O1—C2—N1122.4 (3)C22—C21—H21121.1
O1—C2—C1122.5 (3)C23—C22—C21122.0 (3)
N1—C2—C1115.0 (3)C23—C22—N4119.4 (3)
C4—C3—C8119.9 (3)C21—C22—N4118.6 (3)
C4—C3—N1120.3 (3)C22—C23—C24120.4 (3)
C8—C3—N1119.7 (3)C22—C23—H23119.8
C5—C4—C3120.3 (3)C24—C23—H23119.8
C5—C4—H4119.8C23—C24—C19118.5 (3)
C3—C4—H4119.8C23—C24—C25116.1 (3)
C4—C5—C6118.8 (3)C19—C24—C25125.4 (3)
C4—C5—H5120.6O8—C25—C26119.9 (3)
C6—C5—H5120.6O8—C25—C24119.2 (3)
C5—C6—C7122.3 (3)C26—C25—C24120.9 (2)
C5—C6—N2119.8 (3)C31—C26—C27116.2 (3)
C7—C6—N2117.8 (3)C31—C26—C25123.0 (3)
C8—C7—C6118.8 (3)C27—C26—C25120.8 (3)
C8—C7—H7120.6C28—C27—C26121.7 (4)
C6—C7—H7120.6C28—C27—H31119.1
C7—C8—C3119.7 (3)C26—C27—H31119.1
C7—C8—C9117.4 (3)C29—C28—C27119.7 (4)
C3—C8—C9122.9 (3)C29—C28—H28120.1
O4—C9—C10120.9 (3)C27—C28—H28120.1
O4—C9—C8119.3 (3)C30—C29—C28120.7 (4)
C10—C9—C8119.8 (3)C30—C29—H29119.7
C15—C10—C11116.9 (3)C28—C29—H29119.7
C15—C10—C9119.4 (3)C29—C30—C31118.3 (4)
C11—C10—C9123.7 (3)C29—C30—H30120.8
C12—C11—F1117.7 (3)C31—C30—H30120.8
C12—C11—C10123.7 (3)N3—C32—H32A109.5
F1—C11—C10118.5 (3)N3—C32—H32B109.5
C11—C12—C13117.6 (4)H32A—C32—H32B109.5
C11—C12—H12121.2N3—C32—H32C109.5
C13—C12—H12121.2H32A—C32—H32C109.5
C14—C13—C12121.1 (4)H32B—C32—H32C109.5
C14—C13—H13119.4C2—N1—C3120.1 (2)
C12—C13—H13119.4C2—N1—C16123.0 (2)
C13—C14—C15120.0 (4)C3—N1—C16116.5 (2)
C13—C14—H14120.0O2—N2—O3A105.4 (5)
C15—C14—H14120.0O3A—N2—O2A122.1 (4)
C10—C15—C14120.4 (4)O2—N2—O3124.8 (4)
C10—C15—H15119.8O2A—N2—O3137.8 (7)
C14—C15—H15119.8O2—N2—C6126.2 (5)
N1—C16—H16A109.5O3A—N2—C6126.5 (5)
N1—C16—H16B109.5O2A—N2—C6111.2 (4)
H16A—C16—H16B109.5O3—N2—C6108.9 (5)
N1—C16—H16C109.5C18—N3—C19119.0 (2)
H16A—C16—H16C109.5C18—N3—C32122.9 (3)
H16B—C16—H16C109.5C19—N3—C32117.6 (2)
C18—C17—Cl2115.6 (3)O6—N4—O7A110.7 (7)
C18—C17—Cl2A107.1 (3)O6—N4—O7125.0 (5)
C18—C17—H17A108.4O7A—N4—O6A120.9 (6)
Cl2—C17—H17A108.4O7—N4—O6A126.4 (9)
Cl2A—C17—H17A96.2O6—N4—C22121.7 (5)
C18—C17—H17B108.4O7A—N4—C22123.0 (6)
Cl2—C17—H17B108.4O7—N4—C22112.7 (6)
Cl2A—C17—H17B127.7O6A—N4—C22116.0 (5)
H17A—C17—H17B107.4C26—C31—C30123.3 (4)
O5—C18—N3122.3 (3)C26—C31—H31A118.4
O5—C18—C17122.8 (3)C30—C31—H31A118.4
Cl1—C1—C2—O15.3 (5)C20—C19—C24—C25−178.9 (3)
Cl1A—C1—C2—O1−9.9 (4)N3—C19—C24—C25−0.9 (4)
Cl1—C1—C2—N1−176.5 (3)C23—C24—C25—O8−35.0 (4)
Cl1A—C1—C2—N1168.3 (2)C19—C24—C25—O8144.5 (3)
C8—C3—C4—C51.2 (4)C23—C24—C25—C26142.3 (3)
N1—C3—C4—C5−175.7 (3)C19—C24—C25—C26−38.2 (4)
C3—C4—C5—C61.9 (4)O8—C25—C26—C31139.5 (3)
C4—C5—C6—C7−2.4 (5)C24—C25—C26—C31−37.7 (4)
C4—C5—C6—N2−179.3 (3)O8—C25—C26—C27−39.4 (4)
C5—C6—C7—C8−0.2 (5)C24—C25—C26—C27143.4 (3)
N2—C6—C7—C8176.7 (3)C31—C26—C27—C281.1 (5)
C6—C7—C8—C33.4 (4)C25—C26—C27—C28−179.9 (3)
C6—C7—C8—C9−175.2 (3)C26—C27—C28—C29−1.4 (6)
C4—C3—C8—C7−3.9 (4)C27—C28—C29—C300.2 (6)
N1—C3—C8—C7173.1 (3)C28—C29—C30—C311.3 (6)
C4—C3—C8—C9174.7 (3)O1—C2—N1—C3−2.6 (4)
N1—C3—C8—C9−8.4 (4)C1—C2—N1—C3179.2 (2)
C7—C8—C9—O4−42.2 (4)O1—C2—N1—C16−175.3 (3)
C3—C8—C9—O4139.2 (3)C1—C2—N1—C166.5 (4)
C7—C8—C9—C10136.9 (3)C4—C3—N1—C2−61.7 (4)
C3—C8—C9—C10−41.7 (4)C8—C3—N1—C2121.3 (3)
O4—C9—C10—C15−39.3 (4)C4—C3—N1—C16111.4 (3)
C8—C9—C10—C15141.7 (3)C8—C3—N1—C16−65.6 (3)
O4—C9—C10—C11140.2 (3)C5—C6—N2—O2174.7 (8)
C8—C9—C10—C11−38.9 (4)C7—C6—N2—O2−2.3 (9)
C15—C10—C11—C12−1.4 (5)C5—C6—N2—O3A12.5 (8)
C9—C10—C11—C12179.1 (3)C7—C6—N2—O3A−164.5 (7)
C15—C10—C11—F1176.8 (3)C5—C6—N2—O2A−172.9 (6)
C9—C10—C11—F1−2.7 (4)C7—C6—N2—O2A10.0 (7)
F1—C11—C12—C13−179.0 (3)C5—C6—N2—O3−6.4 (6)
C10—C11—C12—C13−0.8 (5)C7—C6—N2—O3176.6 (5)
C11—C12—C13—C141.6 (6)O5—C18—N3—C195.5 (5)
C12—C13—C14—C15−0.3 (7)C17—C18—N3—C19−175.3 (3)
C11—C10—C15—C142.8 (5)O5—C18—N3—C32177.7 (3)
C9—C10—C15—C14−177.7 (3)C17—C18—N3—C32−3.1 (4)
C13—C14—C15—C10−2.1 (6)C20—C19—N3—C18120.9 (3)
Cl2—C17—C18—O56.0 (5)C24—C19—N3—C18−57.1 (4)
Cl2A—C17—C18—O5−13.0 (4)C20—C19—N3—C32−51.8 (4)
Cl2—C17—C18—N3−173.1 (3)C24—C19—N3—C32130.2 (3)
Cl2A—C17—C18—N3167.8 (3)C23—C22—N4—O6−174.4 (7)
C24—C19—C20—C21−2.3 (6)C21—C22—N4—O65.8 (8)
N3—C19—C20—C21179.6 (3)C23—C22—N4—O7A−20.9 (10)
C19—C20—C21—C221.3 (6)C21—C22—N4—O7A159.2 (10)
C20—C21—C22—C231.6 (6)C23—C22—N4—O7−2.8 (9)
C20—C21—C22—N4−178.6 (3)C21—C22—N4—O7177.3 (8)
C21—C22—C23—C24−3.3 (5)C23—C22—N4—O6A154.2 (7)
N4—C22—C23—C24176.8 (3)C21—C22—N4—O6A−25.7 (8)
C22—C23—C24—C192.2 (4)C27—C26—C31—C300.4 (5)
C22—C23—C24—C25−178.3 (3)C25—C26—C31—C30−178.6 (3)
C20—C19—C24—C230.6 (4)C29—C30—C31—C26−1.6 (5)
N3—C19—C24—C23178.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C32—H32A···O10.982.483.383 (4)154
C29—H29···O5i0.952.503.194 (5)130
C28—H28···Cl1Aii0.952.743.543 (6)143
C17—H17A···O10.992.383.348 (4)165
C16—H16B···O2iii0.982.473.45 (1)176
C7—H7···O7iv0.952.373.31 (2)173
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y, −z+1; (iii) −x+1, −y+1, −z; (iv) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formulaC16H12ClFN2O4
Mr350.73
Crystal system, space groupTriclinic, P1
Temperature (K)200
a, b, c (Å)8.1339 (6), 10.9639 (8), 17.8690 (11)
α, β, γ (°)81.251 (6), 82.239 (6), 87.937 (6)
V (Å3)1560.38 (19)
Z4
Radiation typeMo Kα
µ (mm−1)0.28
Crystal size (mm)0.24 × 0.16 × 0.12
Data collection
DiffractometerOxford Diffraction Xcalibur Eos Gemini
diffractometer
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2010)
Tmin, Tmax0.936, 0.967
No. of measured, independent and
observed [I > 2σ(I)] reflections		13030, 6373, 3774
Rint0.041
(sin θ/λ)max (Å−1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.172, 1.03
No. of reflections6373
No. of parameters448
No. of restraints16
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.32, −0.36

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C32—H32A···O10.982.483.383 (4)153.5
C29—H29···O5i0.952.503.194 (5)130.4
C28—H28···Cl1Aii0.952.743.543 (6)143.2
C17—H17A···O10.992.383.348 (4)164.5
C16—H16B···O2iii0.982.473.45 (1)175.7
C7—H7···O7iv0.952.373.31 (2)173.3
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y, −z+1; (iii) −x+1, −y+1, −z; (iv) −x+1, −y, −z.
 

Acknowledgements

BPS thanks the University of Mysore for access to their research facilities. HSY thanks R. L. Fine Chem, Bangalore, for the title compound. JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 9| September 2011| Pages o2537-o2538
doi:10.1107/S1600536811034969
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