3-(4-Bromo­benzo­yl)-N-phenyl-1,3-oxazolidin-2-imine

The title compound, C₁₇H₁₅BrN₂O₂, was prepared by the reaction of 2-anilino-4-methyl-2-oxazoline with 4-bromo­benzoyl chloride in the presence of potassium tert-butoxide at room temperature. X-ray crystallographic analysis shows that the endo-substituted product is formed.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.075
• wR factor = 0.196
• Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C17 H15 Br N2 O2

Alert level G
ABSTM02_ALERT_3_G  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.578     0.895
            Tmin and Tmax expected:      0.547     0.975
            RR =      1.150
            Please check that your absorption correction is appropriate.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: STADI4 (Stoe & Cie, 1996); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

3-(4-Bromobenzoyl)-N-phenyl-1,3-oxazolidin-2-imine

Crystal data

C17H15BrN2O2	Z = 2
Mr = 359.22	F(000) = 364
Triclinic, P1	Dx = 1.492 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 5.867 (1) Å	Cell parameters from 34 reflections
b = 10.638 (2) Å	θ = 9.6–10.5°
c = 13.982 (3) Å	µ = 2.58 mm^−1
α = 69.44 (3)°	T = 298 K
β = 78.09 (3)°	Plate, colourless
γ = 86.28 (3)°	0.30 × 0.20 × 0.01 mm
V = 799.5 (3) Å^3

Data collection

Stoe Stadi-4 diffractometer	2237 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 27.5°, θmin = 1.6°
ω/2–θ scans	h = 0→7
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 1996)	k = −13→13
Tmin = 0.578, Tmax = 0.895	l = −17→18
3646 measured reflections	3 standard reflections every 60 min
3646 independent reflections	intensity decay: 3.9%

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.196	H-atom parameters constrained
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0712P)^2 + 1.6199P] where P = (Fo^2 + 2Fc^2)/3
3646 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.98 e Å^−3
0 restraints	Δρmin = −0.76 e Å^−3

Special details

Experimental. R_F = 0.5 (ethyl acetate); ¹H NMR (CDCl₃): δ 7.65–7.52 (m, 4H), 7.24–7.18 (m, 2H), 7.03–6.97 (m, 1H), 6.86–6.82 (m, 2H), 4.73–4.65 (m, 1H), 4.50 (dd, 1H, J = 7.1, 8.4 Hz), 4.06 (dd, 1H, J = 4.3, 8.4 Hz), 1.55 (d, 3H, J = 6.3 Hz); ¹³C NMR (CDCl₃): δ 168.8, 145.9, 144.9, 133.7, 130.7, 130.6, 128.6, 126.0, 123.6, 122.8, 71.3, 52.2, 18.0; EIMS m/z 76.9 (57), 154.8 (55), 156.8 (54), 182.8 (100), 184.8 (99), 329.9 (31), 331.9 (30), 358.9 (38, M)

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.

The highest residual peak is situated 0.96?Å from Br and the largest hole is 0.95?Å from Br

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
Br1	0.63171 (13)	0.77555 (8)	0.51242 (6)	0.0745 (3)
O1	0.2226 (9)	1.0005 (5)	0.0660 (4)	0.0707 (14)
O2	−0.1085 (7)	1.3644 (4)	0.1195 (3)	0.0478 (10)
N1	0.0684 (8)	1.1756 (4)	0.1102 (3)	0.0402 (10)
N2	0.1949 (8)	1.2898 (4)	0.2081 (4)	0.0412 (10)
C1	0.4982 (10)	0.8684 (6)	0.3943 (5)	0.0484 (14)
C2	0.2774 (11)	0.9219 (6)	0.4090 (5)	0.0519 (15)
H2	0.1956	0.9128	0.4755	0.062*
C3	0.1808 (10)	0.9896 (6)	0.3219 (4)	0.0476 (14)
H3	0.0334	1.0269	0.3302	0.057*
C4	0.3025 (9)	1.0016 (5)	0.2236 (4)	0.0398 (12)
C5	0.5226 (10)	0.9453 (5)	0.2104 (5)	0.0456 (13)
H5	0.6027	0.9520	0.1440	0.055*
C6	0.6216 (10)	0.8797 (6)	0.2959 (5)	0.0498 (14)
H6	0.7698	0.8434	0.2876	0.060*
C7	0.1997 (10)	1.0590 (5)	0.1277 (4)	0.0452 (13)
C8	−0.0520 (10)	1.2220 (6)	0.0214 (4)	0.0467 (14)
H8	−0.1321	1.1469	0.0167	0.056*
C9	−0.2259 (11)	1.3151 (7)	0.0574 (5)	0.0548 (15)
H9A	−0.2639	1.3885	−0.0016	0.066*
H9B	−0.3681	1.2671	0.0990	0.066*
C10	0.0611 (9)	1.2766 (5)	0.1529 (4)	0.0363 (11)
C11	0.1602 (9)	1.3907 (5)	0.2535 (4)	0.0370 (12)
C12	0.3452 (10)	1.4748 (6)	0.2388 (5)	0.0489 (14)
H12	0.4870	1.4661	0.1974	0.059*
C13	0.3202 (12)	1.5709 (6)	0.2850 (6)	0.0599 (17)
H13	0.4454	1.6272	0.2737	0.072*
C14	0.1154 (13)	1.5854 (7)	0.3472 (5)	0.0605 (18)
H14	0.1001	1.6512	0.3776	0.073*
C15	−0.0686 (12)	1.5007 (7)	0.3641 (5)	0.0580 (17)
H15	−0.2079	1.5080	0.4078	0.070*
C16	−0.0480 (10)	1.4056 (6)	0.3170 (4)	0.0472 (14)
H16	−0.1747	1.3507	0.3278	0.057*
C17	0.1112 (14)	1.2914 (7)	−0.0796 (5)	0.071 (2)
H17A	0.2316	1.2306	−0.0926	0.085*
H17B	0.1800	1.3683	−0.0753	0.085*
H17C	0.0264	1.3199	−0.1353	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0647 (5)	0.0829 (6)	0.0600 (4)	0.0019 (4)	−0.0254 (3)	0.0021 (3)
O1	0.102 (4)	0.060 (3)	0.074 (3)	0.030 (3)	−0.046 (3)	−0.041 (3)
O2	0.050 (2)	0.048 (2)	0.052 (2)	0.0144 (18)	−0.0184 (19)	−0.0231 (19)
N1	0.045 (3)	0.039 (2)	0.041 (2)	0.006 (2)	−0.015 (2)	−0.016 (2)
N2	0.039 (2)	0.041 (3)	0.050 (3)	0.0016 (19)	−0.014 (2)	−0.019 (2)
C1	0.048 (3)	0.041 (3)	0.052 (3)	−0.003 (3)	−0.019 (3)	−0.006 (3)
C2	0.055 (4)	0.050 (3)	0.047 (3)	−0.002 (3)	−0.007 (3)	−0.013 (3)
C3	0.039 (3)	0.050 (3)	0.052 (3)	0.004 (3)	−0.009 (3)	−0.017 (3)
C4	0.042 (3)	0.033 (3)	0.047 (3)	0.001 (2)	−0.011 (2)	−0.016 (2)
C5	0.049 (3)	0.038 (3)	0.048 (3)	0.005 (2)	−0.005 (3)	−0.016 (2)
C6	0.038 (3)	0.046 (3)	0.063 (4)	0.007 (2)	−0.010 (3)	−0.016 (3)
C7	0.057 (4)	0.038 (3)	0.045 (3)	0.001 (3)	−0.016 (3)	−0.017 (3)
C8	0.056 (3)	0.045 (3)	0.046 (3)	0.002 (3)	−0.021 (3)	−0.018 (3)
C9	0.056 (4)	0.062 (4)	0.057 (4)	0.012 (3)	−0.025 (3)	−0.027 (3)
C10	0.036 (3)	0.033 (3)	0.035 (3)	0.001 (2)	−0.004 (2)	−0.009 (2)
C11	0.036 (3)	0.040 (3)	0.038 (3)	0.006 (2)	−0.013 (2)	−0.014 (2)
C12	0.041 (3)	0.052 (3)	0.059 (4)	−0.002 (3)	−0.008 (3)	−0.026 (3)
C13	0.060 (4)	0.051 (4)	0.080 (5)	0.000 (3)	−0.024 (4)	−0.032 (4)
C14	0.083 (5)	0.059 (4)	0.060 (4)	0.021 (4)	−0.035 (4)	−0.038 (3)
C15	0.063 (4)	0.073 (4)	0.041 (3)	0.020 (4)	−0.015 (3)	−0.024 (3)
C16	0.048 (3)	0.055 (4)	0.041 (3)	0.003 (3)	−0.009 (3)	−0.020 (3)
C17	0.100 (6)	0.060 (4)	0.044 (3)	0.010 (4)	−0.010 (4)	−0.010 (3)

Geometric parameters (Å, º)

Br1—C1	1.898 (5)	C8—C17	1.502 (9)
O1—C7	1.212 (7)	C8—C9	1.511 (8)
O2—C10	1.359 (6)	C8—H8	0.9800
O2—C9	1.455 (7)	C9—H9A	0.9700
N1—C7	1.390 (7)	C9—H9B	0.9700
N1—C10	1.396 (7)	C11—C12	1.388 (8)
N1—C8	1.473 (7)	C11—C16	1.390 (8)
N2—C10	1.253 (7)	C12—C13	1.375 (8)
N2—C11	1.411 (7)	C12—H12	0.9300
C1—C6	1.384 (8)	C13—C14	1.365 (10)
C1—C2	1.386 (8)	C13—H13	0.9300
C2—C3	1.392 (8)	C14—C15	1.380 (10)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.378 (8)	C15—C16	1.375 (8)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.393 (7)	C16—H16	0.9300
C4—C7	1.499 (7)	C17—H17A	0.9600
C5—C6	1.379 (8)	C17—H17B	0.9600
C5—H5	0.9300	C17—H17C	0.9600
C6—H6	0.9300
C10—O2—C9	108.9 (4)	O2—C9—H9A	110.9
C7—N1—C10	129.6 (4)	C8—C9—H9A	110.9
C7—N1—C8	120.2 (4)	O2—C9—H9B	110.9
C10—N1—C8	109.1 (4)	C8—C9—H9B	110.9
C10—N2—C11	121.5 (5)	H9A—C9—H9B	108.9
C6—C1—C2	121.5 (5)	N2—C10—O2	125.0 (5)
C6—C1—Br1	119.5 (4)	N2—C10—N1	126.6 (5)
C2—C1—Br1	119.0 (5)	O2—C10—N1	108.3 (4)
C1—C2—C3	118.6 (6)	C12—C11—C16	118.0 (5)
C1—C2—H2	120.7	C12—C11—N2	118.9 (5)
C3—C2—H2	120.7	C16—C11—N2	123.0 (5)
C4—C3—C2	120.3 (5)	C13—C12—C11	120.5 (6)
C4—C3—H3	119.9	C13—C12—H12	119.8
C2—C3—H3	119.9	C11—C12—H12	119.8
C3—C4—C5	120.4 (5)	C14—C13—C12	121.3 (6)
C3—C4—C7	123.2 (5)	C14—C13—H13	119.4
C5—C4—C7	116.0 (5)	C12—C13—H13	119.4
C6—C5—C4	119.8 (5)	C13—C14—C15	118.9 (6)
C6—C5—H5	120.1	C13—C14—H14	120.6
C4—C5—H5	120.1	C15—C14—H14	120.6
C5—C6—C1	119.4 (5)	C16—C15—C14	120.6 (6)
C5—C6—H6	120.3	C16—C15—H15	119.7
C1—C6—H6	120.3	C14—C15—H15	119.7
O1—C7—N1	118.9 (5)	C15—C16—C11	120.7 (6)
O1—C7—C4	119.9 (5)	C15—C16—H16	119.6
N1—C7—C4	121.2 (5)	C11—C16—H16	119.6
N1—C8—C17	112.0 (5)	C8—C17—H17A	109.5
N1—C8—C9	99.1 (4)	C8—C17—H17B	109.5
C17—C8—C9	113.6 (5)	H17A—C17—H17B	109.5
N1—C8—H8	110.6	C8—C17—H17C	109.5
C17—C8—H8	110.6	H17A—C17—H17C	109.5
C9—C8—H8	110.6	H17B—C17—H17C	109.5
O2—C9—C8	104.4 (4)