Methyl 2-[3-(4-bromo­phen­yl)-1,2,4-oxadiazol-5-ylmeth­oxy]phenyl­acetate

The title compound, C₁₈H₁₅FN₂O₄, was synthesized by the reaction of methyl (2-hydroxy­phen­yl)acetate and 3-(4-bromo)phenyl-5-chloro­methyl-1,2,4-oxadiazole. Weak intra­molecular C—H...N hydrogen bonds are observed in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.109
• wR factor = 0.209
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C
RFACG01_ALERT_3_C  The value of the R factor is > 0.10
            R factor given   0.109
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         41 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT082_ALERT_2_C High R1 Value ..................................       0.11
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O4     -   N1      ..       5.98 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     -   C11     ..       5.63 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C10    -   C11     ..       6.31 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O4
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.26
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10

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

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

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXL97.

Methyl 2-[3-(4-bromophenyl)-1,2,4-oxadiazol-5-ylmethoxy]phenylacetate

Crystal data

C18H15FN2O4	F(000) = 712
Mr = 342.32	Dx = 1.395 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.603 (2) Å	θ = 9–12°
b = 9.0170 (18) Å	µ = 0.11 mm^−1
c = 15.692 (3) Å	T = 293 K
β = 96.90 (3)°	Block, colourless
V = 1629.9 (6) Å^3	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	1291 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 26.0°, θmin = 1.8°
ω/2θ scans	h = −14→14
Absorption correction: ψ scan (North et al., 1968)	k = 0→11
Tmin = 0.969, Tmax = 0.989	l = 0→19
3165 measured reflections	3 standard reflections every 200 reflections
3165 independent reflections	intensity decay: none

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)] = 0.109	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.209	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.01P)^2 + 5P] where P = (Fo^2 + 2Fc^2)/3
3165 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.68 e Å^−3
0 restraints	Δρmin = −0.45 e Å^−3

Special details

Experimental. Spectroscopic analysis: ¹H NMR (CDCl₃, δ, p.p.m.): 7.94–7.97 (m, 2H), 7.61–7.63 (m, 2H), 7.23–7.29 (m, 2H), 6.97–7.03 (m, 2H), 5.35 (s, 2H), 3.72 (s, 2H), 3.69 (s, 3H).

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
F	0.4898 (3)	0.2473 (6)	0.4994 (3)	0.0954 (16)
O1	0.7321 (3)	0.7721 (6)	−0.1643 (2)	0.0651 (14)
O2	0.9232 (3)	0.7700 (6)	−0.1265 (2)	0.0691 (15)
O3	0.8133 (3)	0.5368 (6)	0.0158 (3)	0.0631 (13)
O4	0.7548 (4)	0.1632 (5)	0.0800 (3)	0.0666 (14)
N1	0.7001 (5)	0.1150 (7)	0.1501 (3)	0.0599 (16)
N2	0.7229 (4)	0.3618 (6)	0.1527 (3)	0.0501 (14)
C1	0.7515 (5)	0.7550 (9)	−0.2521 (3)	0.0640 (19)
H1B	0.6782	0.7481	−0.2875	0.096*
H1C	0.7955	0.6664	−0.2582	0.096*
H1D	0.7937	0.8391	−0.2694	0.096*
C2	0.8269 (5)	0.7841 (8)	−0.1071 (4)	0.0569 (19)
C3	0.7983 (5)	0.8292 (10)	−0.0167 (4)	0.078 (3)
H3A	0.7959	0.9365	−0.0127	0.093*
H3B	0.7222	0.7914	−0.0083	0.093*
C4	0.8853 (4)	0.7707 (9)	0.0514 (3)	0.0462 (17)
C5	0.9619 (6)	0.8680 (9)	0.1000 (5)	0.066 (2)
H5A	0.9575	0.9693	0.0888	0.079*
C6	1.0449 (6)	0.8144 (9)	0.1655 (4)	0.063 (2)
H6A	1.0954	0.8771	0.1990	0.076*
C7	1.0465 (5)	0.6635 (10)	0.1765 (4)	0.063 (2)
H7A	1.1022	0.6246	0.2181	0.076*
C8	0.9725 (5)	0.5656 (9)	0.1311 (4)	0.0565 (19)
H8A	0.9767	0.4645	0.1428	0.068*
C9	0.8949 (5)	0.6193 (9)	0.0700 (4)	0.0560 (18)
C10	0.8265 (6)	0.3775 (9)	0.0198 (4)	0.064 (2)
H10A	0.9083	0.3533	0.0312	0.076*
H10B	0.7972	0.3352	−0.0354	0.076*
C11	0.7654 (5)	0.3116 (7)	0.0857 (3)	0.0372 (14)
C12	0.6825 (4)	0.2398 (8)	0.1900 (4)	0.0428 (14)
C13	0.6287 (4)	0.2430 (8)	0.2702 (4)	0.0460 (15)
C14	0.5978 (5)	0.1119 (9)	0.3094 (4)	0.0607 (19)
H14A	0.6111	0.0221	0.2831	0.073*
C15	0.5491 (6)	0.1092 (10)	0.3841 (5)	0.069 (2)
H15A	0.5273	0.0209	0.4084	0.083*
C16	0.5340 (5)	0.2449 (13)	0.4217 (4)	0.069 (2)
C17	0.5638 (6)	0.3778 (10)	0.3880 (4)	0.068 (2)
H17A	0.5533	0.4673	0.4155	0.081*
C18	0.6105 (5)	0.3717 (8)	0.3107 (4)	0.0550 (17)
H18A	0.6302	0.4602	0.2856	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F	0.061 (2)	0.174 (5)	0.055 (2)	0.004 (3)	0.0249 (18)	0.006 (3)
O1	0.036 (2)	0.120 (4)	0.038 (2)	0.000 (3)	−0.0031 (18)	0.001 (3)
O2	0.037 (2)	0.129 (5)	0.042 (2)	0.006 (3)	0.0087 (19)	0.002 (3)
O3	0.036 (2)	0.082 (4)	0.070 (3)	−0.006 (2)	0.000 (2)	−0.014 (3)
O4	0.069 (3)	0.064 (3)	0.067 (3)	0.006 (3)	0.011 (3)	0.005 (3)
N1	0.076 (4)	0.062 (4)	0.046 (3)	0.003 (3)	0.025 (3)	0.007 (3)
N2	0.041 (3)	0.066 (4)	0.042 (3)	−0.008 (3)	0.002 (2)	−0.005 (3)
C1	0.058 (4)	0.097 (6)	0.036 (3)	−0.014 (4)	0.001 (3)	−0.005 (4)
C2	0.042 (4)	0.097 (6)	0.030 (3)	0.007 (4)	−0.001 (3)	0.001 (4)
C3	0.044 (4)	0.133 (8)	0.058 (4)	0.012 (4)	0.014 (3)	0.020 (5)
C4	0.020 (3)	0.093 (6)	0.025 (3)	0.003 (3)	0.001 (2)	0.005 (3)
C5	0.052 (4)	0.073 (5)	0.078 (5)	−0.004 (4)	0.029 (4)	0.009 (4)
C6	0.047 (4)	0.092 (6)	0.048 (4)	−0.016 (4)	−0.003 (3)	−0.010 (4)
C7	0.034 (4)	0.110 (7)	0.044 (4)	−0.011 (4)	0.001 (3)	−0.012 (4)
C8	0.029 (3)	0.097 (6)	0.043 (3)	0.001 (4)	0.000 (3)	−0.008 (4)
C9	0.036 (4)	0.090 (6)	0.044 (4)	−0.003 (4)	0.015 (3)	−0.014 (4)
C10	0.051 (4)	0.094 (6)	0.048 (4)	0.002 (4)	0.013 (3)	−0.016 (4)
C11	0.035 (3)	0.058 (4)	0.020 (3)	−0.005 (3)	0.010 (2)	−0.005 (3)
C12	0.026 (3)	0.052 (4)	0.049 (3)	−0.003 (3)	0.002 (2)	0.010 (4)
C13	0.025 (3)	0.067 (4)	0.046 (3)	−0.004 (3)	0.005 (2)	0.000 (4)
C14	0.054 (4)	0.073 (5)	0.058 (4)	0.001 (4)	0.017 (3)	−0.001 (4)
C15	0.058 (5)	0.094 (7)	0.058 (5)	−0.007 (4)	0.020 (4)	0.014 (5)
C16	0.023 (3)	0.142 (8)	0.042 (4)	−0.004 (5)	0.010 (3)	0.002 (6)
C17	0.051 (4)	0.097 (7)	0.057 (5)	0.006 (4)	0.016 (4)	−0.010 (5)
C18	0.044 (4)	0.066 (5)	0.055 (4)	0.000 (4)	0.004 (3)	0.001 (4)

Geometric parameters (Å, º)

F—C16	1.378 (7)	C5—H5A	0.9300
O1—C2	1.338 (6)	C6—C7	1.372 (10)
O1—C1	1.430 (6)	C6—H6A	0.9300
O2—C2	1.200 (6)	C7—C8	1.370 (9)
O3—C9	1.408 (7)	C7—H7A	0.9300
O3—C10	1.445 (8)	C8—C9	1.326 (8)
O4—C11	1.345 (7)	C8—H8A	0.9300
O4—N1	1.403 (6)	C10—C11	1.450 (8)
N1—C12	1.315 (8)	C10—H10A	0.9700
N2—C11	1.295 (6)	C10—H10B	0.9700
N2—C12	1.355 (7)	C12—C13	1.470 (8)
C1—H1B	0.9600	C13—C18	1.352 (9)
C1—H1C	0.9600	C13—C14	1.399 (9)
C1—H1D	0.9600	C14—C15	1.362 (8)
C2—C3	1.551 (8)	C14—H14A	0.9300
C3—C4	1.476 (8)	C15—C16	1.379 (11)
C3—H3A	0.9700	C15—H15A	0.9300
C3—H3B	0.9700	C16—C17	1.371 (11)
C4—C9	1.398 (9)	C17—C18	1.388 (8)
C4—C5	1.407 (9)	C17—H17A	0.9300
C5—C6	1.407 (9)	C18—H18A	0.9300
C2—O1—C1	116.3 (4)	C7—C8—H8A	121.0
C9—O3—C10	116.0 (5)	C8—C9—C4	122.5 (7)
C11—O4—N1	107.6 (5)	C8—C9—O3	126.4 (7)
C12—N1—O4	102.6 (5)	C4—C9—O3	111.1 (6)
C11—N2—C12	104.6 (5)	O3—C10—C11	112.3 (6)
O1—C1—H1B	109.5	O3—C10—H10A	109.1
O1—C1—H1C	109.5	C11—C10—H10A	109.1
H1B—C1—H1C	109.5	O3—C10—H10B	109.1
O1—C1—H1D	109.5	C11—C10—H10B	109.1
H1B—C1—H1D	109.5	H10A—C10—H10B	107.9
H1C—C1—H1D	109.5	N2—C11—O4	111.1 (5)
O2—C2—O1	122.5 (5)	N2—C11—C10	134.6 (6)
O2—C2—C3	124.6 (5)	O4—C11—C10	114.1 (6)
O1—C2—C3	112.7 (5)	N1—C12—N2	114.1 (5)
C4—C3—C2	111.4 (5)	N1—C12—C13	122.0 (6)
C4—C3—H3A	109.3	N2—C12—C13	123.9 (6)
C2—C3—H3A	109.3	C18—C13—C14	117.1 (5)
C4—C3—H3B	109.3	C18—C13—C12	121.7 (6)
C2—C3—H3B	109.3	C14—C13—C12	121.2 (6)
H3A—C3—H3B	108.0	C15—C14—C13	123.3 (7)
C9—C4—C5	117.8 (6)	C15—C14—H14A	118.3
C9—C4—C3	122.0 (6)	C13—C14—H14A	118.3
C5—C4—C3	120.2 (7)	C14—C15—C16	116.1 (7)
C6—C5—C4	121.0 (7)	C14—C15—H15A	122.0
C6—C5—H5A	119.5	C16—C15—H15A	122.0
C4—C5—H5A	119.5	C17—C16—F	117.7 (9)
C7—C6—C5	115.5 (7)	C17—C16—C15	124.1 (6)
C7—C6—H6A	122.2	F—C16—C15	118.2 (8)
C5—C6—H6A	122.2	C16—C17—C18	116.5 (7)
C8—C7—C6	125.1 (7)	C16—C17—H17A	121.8
C8—C7—H7A	117.4	C18—C17—H17A	121.8
C6—C7—H7A	117.4	C13—C18—C17	123.0 (7)
C9—C8—C7	118.0 (8)	C13—C18—H18A	118.5
C9—C8—H8A	121.0	C17—C18—H18A	118.5
C11—O4—N1—C12	0.6 (6)	N1—O4—C11—N2	0.1 (7)
C1—O1—C2—O2	−5.6 (11)	N1—O4—C11—C10	176.8 (5)
C1—O1—C2—C3	170.1 (6)	O3—C10—C11—N2	−17.6 (10)
O2—C2—C3—C4	−33.4 (11)	O3—C10—C11—O4	166.8 (5)
O1—C2—C3—C4	151.1 (6)	O4—N1—C12—N2	−1.2 (6)
C2—C3—C4—C9	−69.3 (8)	O4—N1—C12—C13	−178.4 (5)
C2—C3—C4—C5	110.9 (7)	C11—N2—C12—N1	1.3 (6)
C9—C4—C5—C6	−0.2 (9)	C11—N2—C12—C13	178.5 (5)
C3—C4—C5—C6	179.6 (6)	N1—C12—C13—C18	−179.7 (6)
C4—C5—C6—C7	1.1 (10)	N2—C12—C13—C18	3.3 (8)
C5—C6—C7—C8	−2.0 (11)	N1—C12—C13—C14	2.5 (8)
C6—C7—C8—C9	1.9 (11)	N2—C12—C13—C14	−174.5 (5)
C7—C8—C9—C4	−0.8 (9)	C18—C13—C14—C15	1.3 (9)
C7—C8—C9—O3	178.9 (6)	C12—C13—C14—C15	179.2 (6)
C5—C4—C9—C8	0.0 (9)	C13—C14—C15—C16	−1.7 (10)
C3—C4—C9—C8	−179.8 (5)	C14—C15—C16—C17	0.6 (10)
C5—C4—C9—O3	−179.7 (5)	C14—C15—C16—F	−177.2 (5)
C3—C4—C9—O3	0.5 (8)	F—C16—C17—C18	178.6 (5)
C10—O3—C9—C8	−8.9 (9)	C15—C16—C17—C18	0.8 (10)
C10—O3—C9—C4	170.7 (5)	C14—C13—C18—C17	0.3 (9)
C9—O3—C10—C11	87.9 (6)	C12—C13—C18—C17	−177.6 (5)
C12—N2—C11—O4	−0.8 (6)	C16—C17—C18—C13	−1.3 (9)
C12—N2—C11—C10	−176.5 (6)