Acta Cryst.(2002). E58, o1111±o1112 DOI: 10.1107/S1600536802016148 Bishwa Nath Yadavet al. C14H8N2O4
o1111
organic papers
Acta Crystallographica Section E Structure Reports
Online
ISSN 1600-5368
2-(2-Nitrophenyl)-4,5-benz-1,3-oxazin-6-one
Bishwa Nath Yadav, Shambhu Prasad and Satya Murti Prasad*
Department of Physics, Ranchi University, Ranchi 834008, India.
Correspondence e-mail: prasadsm50@hotmail.com
Key indicators Single-crystal X-ray study T= 293 K
Mean(C±C) = 0.003 AÊ Rfactor = 0.038 wRfactor = 0.105
Data-to-parameter ratio = 11.7
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2002 International Union of Crystallography Printed in Great Britain ± all rights reserved
In the title compound, C14H8N2O4, the planar benzoxazinone
moiety forms a dihedral angle of 54.54 (8) with the phenyl
ring. The crystal structure is stabilized by weak CÐH O hydrogen bonds and van der Waals interactions.
Comment
The preparation of several new 2-phenyl substituted phenyl benzoxazinones and evaluation of their biological activity against some pathogenic fungi and bacteria have been reported (Kumaret al., 1977). A project has been undertaken by us to study the crystal structures of some of these benzoxazinones to establish their stereochemistry. The present paper reports the structure of the title compound, C14H8N2O4(I), a benzoxazinone derivative.
A displacement ellipsoid plot of the molecule is shown in Fig. 1. The benzoxazinone moiety is essentially planar, with O2 deviating by a maximum of 0.037 (1) AÊ, and it forms a di-hedral angle of 54.54 (8) with the phenyl ring. The nitro
group is twisted out of the phenyl ring plane by 19.63 (11).
Although there is no ÐNH or ÐOH group available in the structure to form strong hydrogen bonds, the C atoms are involved in the formation of weak CÐH O hydrogen bonds with the O atoms O3 and O4 of the nitro group (Table 2 and Fig. 2). Some other short intermolecular contacts are listed in Table 3.
Experimental
The title compound was obtained by the reaction ofo-nitrobenzoyl chloride with anthranilic acid at 273 K (Kumar et al., 1977). The precipitate was recrystallized from EtOH/H2O (4:1) as pale-yellow
crystals. Crystal data
C14H8N2O4
Mr= 268.22
Monoclinic,P21=c
a= 4.1824 (6) AÊ
b= 22.191 (2) AÊ
c= 12.767 (1) AÊ = 93.26 (1)
V= 1183.0 (2) AÊ3
Z= 4
Dx= 1.506 Mg mÿ3
CuKradiation Cell parameters from 25
re¯ections = 11.2±35.2
= 0.96 mmÿ1
T= 293 (2) K Needle, light yellow 0.360.240.15 mm
Data collection
Enraf±Nonius CAD-4 diffractometer !±2scans
Absorption correction: scan (Northet al., 1968)
Tmin= 0.968,Tmax= 0.999
2438 measured re¯ections 2130 independent re¯ections 1739 re¯ections withI> 2(I)
Rint= 0.014
max= 67.7
h= 0!5
k= 0!26
l=ÿ15!15 3 standard re¯ections
frequency: 60 min intensity decay: none
Re®nement
Re®nement onF2
R[F2> 2(F2)] = 0.038
wR(F2) = 0.105
S= 1.06 2130 re¯ections 182 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.0456P)2
+ 0.4728P]
whereP= (Fo2+ 2Fc2)/3
(/)max< 0.001
max= 0.24 e AÊÿ3
min=ÿ0.15 e AÊÿ3
Extinction correction:SHELXL97 Extinction coef®cient: 0.0048 (6)
Table 1
Selected geometric parameters (AÊ,).
C5ÐN1 1.401 (2)
C7ÐO1 1.193 (2)
C7ÐO2 1.392 (2)
C8ÐN1 1.265 (2)
C8ÐO2 1.366 (2)
C14ÐN2 1.469 (2)
N2ÐO3 1.213 (2)
N2ÐO4 1.216 (2)
O1ÐC7ÐO2 117.08 (17)
O1ÐC7ÐC6 127.93 (17)
N1ÐC8ÐO2 126.33 (15)
O2ÐC8ÐC9 112.39 (14)
O3ÐN2ÐO4 123.76 (17)
O3ÐN2ÐC14 118.43 (15)
N1ÐC8ÐC9ÐC10 ÿ54.3 (2)
O2ÐC8ÐC9ÐC10 121.85 (18) N1ÐC8ÐC9ÐC14 127.61 (19)
O2ÐC8ÐC9ÐC14 ÿ56.3 (2)
C13ÐC14ÐN2ÐO3 158.17 (18)
C9ÐC14ÐN2ÐO3 ÿ18.0 (3)
C13ÐC14ÐN2ÐO4 ÿ20.3 (3) C9ÐC14ÐN2ÐO4 163.51 (19)
Table 2
Hydrogen-bonding geometry (AÊ,).
DÐH A DÐH H A D A DÐH A
C1ÐH1 O1iv 0.93 2.75 3.434 (2) 131
C12ÐH12 O1v 0.93 2.91 3.470 (3) 120
C13ÐH13 O1v 0.93 2.68 3.353 (2) 130
C12ÐH12 O3vi 0.93 2.61 3.386 (2) 141
C11ÐH11 O4vi 0.93 2.79 3.633 (3) 151
C2ÐH2 O4vii 0.93 2.84 3.342 (3) 115
C3ÐH3 O4vii 0.93 2.53 3.189 (2) 129
Symmetry codes: (iv) ÿx;ÿy;ÿz; (v) x;1
2ÿy;12z; (vi) xÿ1;12ÿy;12z; (vii) 1ÿx;yÿ1
2;12ÿz.
Table 3
Some short inter-molecular contacts shorter than 3.5 AÊ.
N1 C10i 3.353 (3)
O2 O3ii 3.045 (3)
O2 C5ii 3.485 (3)
O3 C9i 3.200 (3)
O3 C14i 3.103 (3)
O4 C11iii 3.245 (3)
Symmetry codes: (i) 1x;y;z; (ii)xÿ1;y;z; (iii)x;1 2ÿy;zÿ12.
After checking their presence in a difference map, all the H atoms were positioned geometrically and were treated as riding on their aromatic parent C atoms, with CÐH = 0.93 AÊ.
Data collection: CAD-4 EXPRESS (Enraf±Nonius, 1994); cell re®nement:CAD-4EXPRESS; data reduction:MoLEN(Fair,1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure:SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication:SHELXL97.
The authors thank Dr S. Kumar, Department of Chemistry, Ranchi University, Ranchi, and his co-workers for the gift of the crystals, and the Indian Institute of Technology, Chennai, India, for the collection of X-ray diffraction data.
References
Enraf±Nonius (1994).CAD-4EXPRESS. Enraf±Nonius, Delft, The Nether-lands.
Fair, C. K. (1990).MolEN.Enraf±Nonius, Delft, The Netherlands. Farrugia, L. J. (1997).J. Appl. Cryst.30, 565.
Kumar, S., Srivastava, A. K. & Sarkar, P. C. (1977).J. Inst. Chem. India,69, 116±117.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968).Acta Cryst.A24, 351± 359.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of GoÈttingen, Germany.
Figure 1
AnORTEP-3 plot (Farrugia, 1997) of the molecule, with 50% probability displacement ellipsoids for non-H atoms.
Figure 2
A view of the weak CÐH O hydrogen bonds in the title compound. Symmetry codes: (i)ÿx,ÿy,ÿz, (ii)x,1
2ÿy,12+z(iii) = 1 +x,12ÿy,12+z
and (iv) = 1ÿx,1
supporting information
sup-1
Acta Cryst. (2002). E58, o1111–o1112supporting information
Acta Cryst. (2002). E58, o1111–o1112 [doi:10.1107/S1600536802016148]
2-(2-Nitrophenyl)-4,5-benz-1,3-oxazin-6-one
Bishwa Nath Yadav, Shambhu Prasad and Satya Murti Prasad
S1. Comment
The preparation of several new 2-phenyl substituted phenyl benzoxinones and evaluation of their biological activity
against some pathogenic fungi and bacteria have been reported (Kumar et al., 1997). A project has been undertaken by us
to study the crystal structures of some of these benzoxinones to establish their stereochemistry. The present paper reports
the structure of the title compound, C14H8N2O4 (I), a benzoxinone derivative.
A displacement ellipsoid plot of the title molecule is shown in Fig. 1. The benzoxinone moiety is essentially planar, with
O2 deviating a maximum of 0.037 (1) Å and it forms a dihedral angle of 54.54 (8)° with the phenyl ring. The nitro group
is twisted out of the phenyl ring plane by 19.63 (11)°. Although there is no —NH or —OH group available in the
structure to form strong hydrogen bonds, the C atoms are involved in the formation of weak C—H···O hydrogen bonds
with the oxygen atoms O3 and O4 of the nitro group (Table 2 and Fig. 2). Some other short intermolecular contacts are
listed in Table 3.
S2. Experimental
The title compound was obtained by the reaction of o-nitrobenzoyl chloride on anthralinic acid in cold (273 K) (Kumar et
al., 1997). The precipitate was recrystallized from EtOH/H2O (4:1) as pale yellow crystals.
S3. Refinement
After checking their presence in a difference map, all the hydrogen atoms were fixed and geometrically were treated as
Figure 1
An ORTEP-3 plot (Farrugia, 1997) of the molecule, with 50% probability displacement ellipsoids for non-hydrogen
atoms.
Figure 2
A view of the weak C—H···O hydrogen bonds in the title compound. Symmetry codes: (i) −x, −y, −z, (ii) x, 1/2 − y, −1/2
+ z (iii) = 1 + x, 1/2 − y, −1/2 + z and (iv) = 1 − x, 1/2 + y, 1/2 − z.
2-(2′-Nitrophenyl)-4,5-benz-1,3-oxazin-6-one
Crystal data
C14H8N2O4
Mr = 268.22 Monoclinic, P21/c
Hall symbol: -P 2ybc a = 4.1824 (6) Å b = 22.191 (2) Å
c = 12.767 (1) Å β = 93.26 (1)° V = 1183.0 (2) Å3
[image:4.610.128.482.338.541.2]supporting information
sup-3
Acta Cryst. (2002). E58, o1111–o1112Cu Kα radiation, λ = 1.5418 Å Cell parameters from 25 reflections θ = 11.2–35.2°
µ = 0.96 mm−1
T = 293 K
Needles, light yellow 0.36 × 0.24 × 0.15 mm
Data collection
Enraf-Nonius CAD-4 diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
ω–2θ scans
Absorption correction: ψ scan (North et al., 1968)
Tmin = 0.968, Tmax = 0.999
2438 measured reflections
2130 independent reflections 1739 reflections with I > 2σ(I) Rint = 0.014
θmax = 67.7°, θmin = 4.0°
h = 0→5 k = 0→26 l = −15→15
3 standard reflections every 60 min intensity decay: none
Refinement
Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.038
wR(F2) = 0.105
S = 1.06 2130 reflections 182 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained w = 1/[σ2(F
o2) + (0.0456P)2 + 0.4728P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.24 e Å−3
Δρmin = −0.15 e Å−3
Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Extinction coefficient: 0.0048 (6)
Special details
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)
x y z Uiso*/Ueq
C1 0.3229 (5) −0.01215 (9) 0.13071 (15) 0.0488 (5)
H1 0.2493 −0.0088 0.0608 0.063*
C2 0.5058 (6) −0.06047 (9) 0.16334 (17) 0.0550 (5)
H2 0.5558 −0.0902 0.1156 0.069*
C3 0.6167 (5) −0.06517 (8) 0.26742 (17) 0.0525 (5)
H3 0.7425 −0.0980 0.2887 0.068*
C4 0.5443 (5) −0.02231 (8) 0.33934 (15) 0.0454 (4)
H4 0.6196 −0.0262 0.4090 0.054*
C5 0.3573 (4) 0.02718 (7) 0.30789 (13) 0.0369 (4)
C7 0.0492 (5) 0.08343 (8) 0.17082 (13) 0.0425 (4)
C8 0.1188 (4) 0.11534 (7) 0.35014 (13) 0.0361 (4)
C9 0.0280 (4) 0.16375 (7) 0.42316 (13) 0.0364 (4)
C10 −0.1239 (5) 0.14748 (9) 0.51246 (14) 0.0468 (5)
H10 −0.1578 0.1069 0.5265 0.056*
C11 −0.2260 (5) 0.19071 (10) 0.58126 (16) 0.0553 (5)
H11 −0.3282 0.1789 0.6408 0.065*
C12 −0.1777 (5) 0.25082 (10) 0.56230 (16) 0.0553 (5)
H12 −0.2487 0.2796 0.6086 0.064*
C13 −0.0248 (5) 0.26852 (8) 0.47518 (15) 0.0474 (5)
H13 0.0099 0.3092 0.4622 0.065*
C14 0.0768 (4) 0.22512 (8) 0.40701 (13) 0.0383 (4)
N1 0.2876 (4) 0.07100 (6) 0.38216 (11) 0.0390 (4)
N2 0.2595 (4) 0.24605 (7) 0.31904 (12) 0.0469 (4)
O1 −0.0650 (4) 0.09470 (7) 0.08535 (10) 0.0645 (5)
O2 −0.0164 (3) 0.12322 (5) 0.25113 (9) 0.0440 (3)
O3 0.4312 (4) 0.21035 (7) 0.27731 (11) 0.0570 (4)
O4 0.2345 (6) 0.29876 (7) 0.29373 (14) 0.0860 (6)
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C1 0.0628 (13) 0.0459 (11) 0.0380 (10) −0.0012 (9) 0.0051 (9) −0.0068 (8) C2 0.0688 (14) 0.0393 (10) 0.0577 (12) 0.0042 (9) 0.0120 (10) −0.0132 (9) C3 0.0607 (13) 0.0354 (10) 0.0618 (12) 0.0068 (9) 0.0058 (10) −0.0006 (9) C4 0.0556 (12) 0.0363 (9) 0.0439 (10) −0.0002 (8) 0.0000 (8) 0.0037 (8) C5 0.0429 (10) 0.0309 (8) 0.0369 (9) −0.0056 (7) 0.0038 (7) −0.0021 (7) C6 0.0455 (10) 0.0325 (8) 0.0359 (9) −0.0044 (7) 0.0052 (7) −0.0012 (7) C7 0.0573 (12) 0.0370 (9) 0.0329 (9) −0.0019 (8) 0.0011 (8) −0.0027 (7) C8 0.0455 (10) 0.0312 (8) 0.0315 (8) −0.0064 (7) 0.0001 (7) 0.0011 (7) C9 0.0397 (10) 0.0358 (9) 0.0335 (8) −0.0009 (7) −0.0003 (7) −0.0032 (7) C10 0.0542 (12) 0.0444 (10) 0.0419 (10) −0.0074 (9) 0.0045 (8) 0.0007 (8) C11 0.0569 (12) 0.0687 (14) 0.0418 (10) −0.0086 (10) 0.0148 (9) −0.0085 (9) C12 0.0584 (13) 0.0575 (12) 0.0509 (11) 0.0016 (10) 0.0101 (9) −0.0200 (9) C13 0.0560 (12) 0.0371 (10) 0.0489 (11) 0.0010 (8) 0.0023 (9) −0.0110 (8) C14 0.0421 (10) 0.0379 (9) 0.0349 (9) −0.0009 (7) 0.0022 (7) −0.0026 (7) N1 0.0508 (9) 0.0321 (7) 0.0339 (7) −0.0008 (6) 0.0005 (6) −0.0004 (6) N2 0.0602 (10) 0.0383 (8) 0.0420 (8) −0.0057 (7) 0.0023 (7) 0.0011 (7) O1 0.0994 (12) 0.0560 (9) 0.0362 (7) 0.0131 (8) −0.0125 (7) −0.0019 (6) O2 0.0592 (8) 0.0386 (7) 0.0335 (6) 0.0087 (6) −0.0047 (5) −0.0040 (5) O3 0.0596 (9) 0.0585 (9) 0.0548 (8) 0.0009 (7) 0.0200 (7) −0.0002 (7) O4 0.1446 (18) 0.0398 (9) 0.0768 (12) −0.0022 (9) 0.0351 (12) 0.0139 (7)
Geometric parameters (Å, º)
C1—C2 1.368 (3) C8—O2 1.366 (2)
C1—C6 1.396 (2) C8—C9 1.486 (2)
supporting information
sup-5
Acta Cryst. (2002). E58, o1111–o1112C2—C3 1.386 (3) C9—C14 1.394 (2)
C2—H2 0.93 C10—C11 1.385 (3)
C3—C4 1.368 (3) C10—H10 0.93
C3—H3 0.93 C11—C12 1.373 (3)
C4—C5 1.394 (2) C11—H11 0.93
C4—H4 0.93 C12—C13 1.371 (3)
C5—C6 1.396 (2) C12—H12 0.93
C5—N1 1.401 (2) C13—C14 1.381 (2)
C6—C7 1.453 (3) C13—H13 0.93
C7—O1 1.193 (2) C14—N2 1.469 (2)
C7—O2 1.392 (2) N2—O3 1.213 (2)
C8—N1 1.265 (2) N2—O4 1.216 (2)
N1···C10i 3.353 (3) O3···C9i 3.200 (3)
O2···O3ii 3.045 (3) O3···C14i 3.103 (3)
O2···C5ii 3.485 (3) O4···C11iii 3.245 (3)
C2—C1—C6 119.63 (18) C10—C9—C14 117.03 (16)
C2—C1—H1 120.2 C10—C9—C8 118.28 (15)
C6—C1—H1 120.2 C14—C9—C8 124.66 (15)
C1—C2—C3 120.10 (18) C9—C10—C11 120.95 (18)
C1—C2—H2 119.9 C9—C10—H10 119.5
C3—C2—H2 119.9 C11—C10—H10 119.5
C4—C3—C2 121.09 (18) C12—C11—C10 120.51 (18)
C4—C3—H3 119.5 C12—C11—H11 119.7
C2—C3—H3 119.5 C10—C11—H11 119.7
C3—C4—C5 119.77 (18) C13—C12—C11 120.09 (18)
C3—C4—H4 120.1 C13—C12—H12 120.0
C5—C4—H4 120.1 C11—C12—H12 120.0
C4—C5—C6 119.18 (16) C12—C13—C14 119.06 (18)
C4—C5—N1 119.14 (16) C12—C13—H13 120.5
C6—C5—N1 121.67 (15) C14—C13—H13 120.5
C5—C6—C1 120.22 (17) C13—C14—C9 122.35 (17)
C5—C6—C7 118.96 (15) C13—C14—N2 116.96 (16)
C1—C6—C7 120.81 (16) C9—C14—N2 120.58 (15)
O1—C7—O2 117.08 (17) C8—N1—C5 117.07 (14)
O1—C7—C6 127.93 (17) O3—N2—O4 123.76 (17)
O2—C7—C6 114.98 (14) O3—N2—C14 118.43 (15)
N1—C8—O2 126.33 (15) O4—N2—C14 117.79 (17)
N1—C8—C9 121.15 (15) C8—O2—C7 120.76 (14)
O2—C8—C9 112.39 (14)
C6—C1—C2—C3 −0.4 (3) C9—C10—C11—C12 −0.2 (3)
C1—C2—C3—C4 0.6 (3) C10—C11—C12—C13 −0.6 (3)
C2—C3—C4—C5 −0.3 (3) C11—C12—C13—C14 0.5 (3)
C3—C4—C5—C6 −0.1 (3) C12—C13—C14—C9 0.4 (3)
C3—C4—C5—N1 −179.40 (17) C12—C13—C14—N2 −175.73 (18)
N1—C5—C6—C1 179.57 (16) C8—C9—C14—C13 177.09 (17)
C4—C5—C6—C7 179.26 (17) C10—C9—C14—N2 174.90 (16)
N1—C5—C6—C7 −1.5 (3) C8—C9—C14—N2 −6.9 (3)
C2—C1—C6—C5 −0.1 (3) O2—C8—N1—C5 3.6 (3)
C2—C1—C6—C7 −179.00 (18) C9—C8—N1—C5 179.14 (15)
C5—C6—C7—O1 −179.8 (2) C4—C5—N1—C8 179.57 (16)
C1—C6—C7—O1 −0.9 (3) C6—C5—N1—C8 0.3 (2)
C5—C6—C7—O2 −0.9 (2) C13—C14—N2—O3 158.17 (18)
C1—C6—C7—O2 178.02 (16) C9—C14—N2—O3 −18.0 (3)
N1—C8—C9—C10 −54.3 (2) C13—C14—N2—O4 −20.3 (3)
O2—C8—C9—C10 121.85 (18) C9—C14—N2—O4 163.51 (19)
N1—C8—C9—C14 127.61 (19) N1—C8—O2—C7 −6.3 (3)
O2—C8—C9—C14 −56.3 (2) C9—C8—O2—C7 177.87 (15)
C14—C9—C10—C11 0.9 (3) O1—C7—O2—C8 −176.52 (17)
C8—C9—C10—C11 −177.32 (18) C6—C7—O2—C8 4.4 (2)
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) x, −y+1/2, z−1/2.
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
C1—H1···O1iv 0.93 2.75 3.434 (2) 131
C12—H12···O1v 0.93 2.91 3.470 (3) 120
C13—H13···O1v 0.93 2.68 3.353 (2) 130
C12—H12···O3vi 0.93 2.61 3.386 (2) 141
C11—H11···O4vi 0.93 2.79 3.633 (3) 151
C2—H2···O4vii 0.93 2.84 3.342 (3) 115
C3—H3···O4vii 0.93 2.53 3.189 (2) 129
