2-(3-Nitro­phen­yl)-2-oxazoline

The title compound, C₉H₈N₂O₃, was obtained by a zinc chloride-promoted addition and ring-closure reaction involving 3-nitro­benzonitrile and 2-ethano­lamine. The planar oxazoline and aromatic rings of the mol­ecule are almost coplanar, with a dihedral angle of 8.79 (5)° between them. The oxazoline ring is disordered over two positions, rendering the oxygen and nitro­gen positions indistinguishable.

Key indicators

• Single-crystal X-ray study
• T = 198 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.036
• wR factor = 0.110
• Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT301_ALERT_3_C Main Residue  Disorder .........................      12.00 Perc.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.

2-(3-Nitrophenyl)-2-oxazoline

Crystal data

C9H8N2O3	F(000) = 400
Mr = 192.17	Dx = 1.497 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2968 reflections
a = 6.0910 (5) Å	θ = 3.4–27.3°
b = 19.7825 (18) Å	µ = 0.12 mm^−1
c = 7.1119 (7) Å	T = 198 K
β = 95.584 (2)°	Plate, colourless
V = 852.88 (13) Å^3	0.48 × 0.23 × 0.05 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	1902 independent reflections
Radiation source: fine-focus sealed tube, Bruker AXS SMART1000/P4	1466 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997b)	h = −7→7
Tmin = 0.872, Tmax = 0.994	k = −25→24
5794 measured reflections	l = −8→8

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: difference Fourier map
wR(F^2) = 0.110	All H-atom parameters refined
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0634P)^2] where P = (Fo^2 + 2Fc^2)/3
1902 reflections	(Δ/σ)max < 0.001
159 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

Experimental. Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections.

1H NMR (CDCl3, 300 MHz, p.p.m.): δ 3.76 (s, br, 2H, NH2), 4.05 (t, 2H, J = 9.6 Hz: CH2), 4.42 (t, 2H: CH2), 6.80 (m, 1H, ArH), 7.20 (t, 1H, ArH), 7.29 (m, 2H, ArH); IR (KBr): 1646 (s), 1231 (s), 1083 (s).

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.24042 (17)	0.10833 (5)	0.30583 (15)	0.0381 (3)
O1	0.31635 (18)	0.05341 (5)	0.35663 (15)	0.0559 (3)
O2	0.05629 (16)	0.11549 (5)	0.22320 (15)	0.0520 (3)
C1	0.37635 (18)	0.16858 (6)	0.34727 (16)	0.0296 (3)
C2	0.28217 (19)	0.23123 (6)	0.31350 (16)	0.0280 (3)
C3	0.40887 (18)	0.28843 (6)	0.35840 (16)	0.0283 (3)
C4	0.6275 (2)	0.28106 (7)	0.43408 (17)	0.0334 (3)
C5	0.7169 (2)	0.21749 (7)	0.46451 (18)	0.0372 (3)
C6	0.5925 (2)	0.16040 (7)	0.42235 (17)	0.0356 (3)
C7	0.3088 (2)	0.35532 (6)	0.32997 (16)	0.0327 (3)
N8	0.11211 (16)	0.36198 (5)	0.24134 (14)	0.0399 (3)	0.50
O8	0.11211 (16)	0.36198 (5)	0.24134 (14)	0.0399 (3)	0.50
C9	0.0574 (2)	0.43370 (7)	0.2513 (2)	0.0453 (4)
C10	0.2657 (3)	0.46592 (8)	0.3420 (3)	0.0519 (4)
O11	0.41284 (17)	0.40924 (5)	0.39606 (15)	0.0455 (3)	0.50
N11	0.41284 (17)	0.40924 (5)	0.39606 (15)	0.0455 (3)	0.50
H2	0.134 (3)	0.2372 (7)	0.266 (2)	0.046 (4)*
H4	0.714 (2)	0.3197 (8)	0.462 (2)	0.041 (4)*
H5	0.865 (3)	0.2127 (8)	0.515 (2)	0.055 (4)*
H6	0.652 (2)	0.1162 (8)	0.4451 (19)	0.041 (4)*
H9A	0.013 (2)	0.4510 (8)	0.125 (2)	0.051 (4)*
H9B	−0.069 (2)	0.4382 (8)	0.3281 (19)	0.054 (4)*
H10A	0.336 (3)	0.4922 (9)	0.258 (2)	0.070 (5)*
H10B	0.244 (3)	0.4909 (9)	0.458 (2)	0.070 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0419 (6)	0.0334 (7)	0.0403 (6)	−0.0006 (5)	0.0111 (5)	−0.0048 (5)
O1	0.0684 (7)	0.0308 (6)	0.0694 (7)	0.0035 (5)	0.0116 (5)	0.0028 (5)
O2	0.0403 (6)	0.0468 (6)	0.0679 (7)	−0.0075 (4)	−0.0003 (5)	−0.0128 (5)
C1	0.0311 (6)	0.0334 (7)	0.0250 (6)	0.0003 (5)	0.0059 (4)	−0.0015 (5)
C2	0.0242 (5)	0.0348 (7)	0.0251 (6)	0.0011 (5)	0.0025 (4)	−0.0011 (5)
C3	0.0290 (6)	0.0344 (7)	0.0219 (6)	−0.0008 (5)	0.0043 (4)	−0.0014 (5)
C4	0.0296 (6)	0.0432 (8)	0.0274 (6)	−0.0062 (5)	0.0026 (5)	−0.0031 (5)
C5	0.0256 (6)	0.0559 (9)	0.0296 (6)	0.0041 (6)	0.0000 (5)	0.0000 (6)
C6	0.0348 (6)	0.0416 (8)	0.0308 (6)	0.0103 (5)	0.0044 (5)	0.0030 (5)
C7	0.0395 (7)	0.0328 (7)	0.0263 (6)	−0.0008 (5)	0.0065 (5)	−0.0023 (5)
N8	0.0384 (5)	0.0306 (6)	0.0492 (6)	0.0039 (4)	−0.0037 (4)	−0.0028 (4)
O8	0.0384 (5)	0.0306 (6)	0.0492 (6)	0.0039 (4)	−0.0037 (4)	−0.0028 (4)
C9	0.0528 (8)	0.0335 (8)	0.0501 (9)	0.0095 (6)	0.0077 (7)	0.0005 (6)
C10	0.0655 (10)	0.0304 (8)	0.0595 (10)	−0.0007 (7)	0.0050 (8)	−0.0037 (7)
O11	0.0479 (6)	0.0339 (6)	0.0529 (6)	−0.0050 (5)	−0.0036 (5)	−0.0072 (5)
N11	0.0479 (6)	0.0339 (6)	0.0529 (6)	−0.0050 (5)	−0.0036 (5)	−0.0072 (5)

Geometric parameters (Å, º)

N1—O1	1.2217 (14)	C5—H5	0.941 (16)
N1—O2	1.2227 (14)	C6—H6	0.954 (15)
N1—C1	1.4647 (15)	C7—N8	1.3048 (15)
C1—C2	1.3770 (16)	C7—O11	1.3049 (15)
C1—C6	1.3813 (17)	N8—C9	1.4607 (17)
C2—C3	1.3893 (16)	C9—C10	1.508 (2)
C2—H2	0.942 (16)	C9—H9A	0.977 (14)
C3—C4	1.3947 (16)	C9—H9B	0.991 (14)
C3—C7	1.4627 (17)	C10—O11	1.4632 (18)
C4—C5	1.3791 (18)	C10—H10A	0.925 (19)
C4—H4	0.940 (15)	C10—H10B	0.981 (17)
C5—C6	1.3767 (19)
O1—N1—O2	123.25 (11)	C5—C6—H6	121.4 (8)
O1—N1—C1	118.28 (11)	C1—C6—H6	120.4 (8)
O2—N1—C1	118.47 (10)	N8—C7—O11	118.84 (11)
C2—C1—C6	122.55 (11)	N8—C7—C3	120.59 (10)
C2—C1—N1	118.65 (10)	O11—C7—C3	120.56 (11)
C6—C1—N1	118.78 (11)	C7—N8—C9	106.14 (10)
C1—C2—C3	118.71 (11)	N8—C9—C10	104.16 (11)
C1—C2—H2	123.0 (9)	N8—C9—H9A	109.9 (9)
C3—C2—H2	118.2 (9)	C10—C9—H9A	113.2 (9)
C2—C3—C4	119.46 (11)	N8—C9—H9B	107.9 (9)
C2—C3—C7	119.36 (10)	C10—C9—H9B	113.2 (9)
C4—C3—C7	121.16 (11)	H9A—C9—H9B	108.3 (13)
C5—C4—C3	120.24 (12)	O11—C10—C9	104.88 (12)
C5—C4—H4	120.2 (9)	O11—C10—H10A	106.9 (12)
C3—C4—H4	119.6 (9)	C9—C10—H10A	112.4 (11)
C6—C5—C4	120.88 (11)	O11—C10—H10B	107.3 (10)
C6—C5—H5	119.1 (10)	C9—C10—H10B	113.2 (10)
C4—C5—H5	120.0 (10)	H10A—C10—H10B	111.6 (15)
C5—C6—C1	118.16 (12)	C7—O11—C10	105.56 (11)