2-(4-Fluoro­phen­oxy)-N-methyl­acetamide

The asymmetric unit of the title compound, C₉H₁₀FNO₂, contains two mol­ecules. Intra- and inter­molecular N—H...O and C—H...F hydrogen bonds link the mol­ecules into a three-dimensional framework; they seem to be effective in the stabilization of the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.070
• wR factor = 0.194
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.02
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C9

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

   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1985); 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 (Bruker, 2000); software used to prepare material for publication: SHELXTL.

2-(4-fluorophenoxy)-N-methylacetamide

Crystal data

C9H10FNO2	F(000) = 768
Mr = 183.18	Dx = 1.338 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 7.6070 (15) Å	θ = 10–13°
b = 15.623 (3) Å	µ = 0.11 mm^−1
c = 15.306 (3) Å	T = 298 K
β = 90.16 (3)°	Block, colorless
V = 1819.0 (6) Å^3	0.30 × 0.20 × 0.10 mm
Z = 8

Data collection

Enraf–Nonius CAD-4 diffractometer	1864 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 26.0°, θmin = 1.9°
ω/2θ scans	h = −9→9
Absorption correction: ψ scan (North et al., 1968)	k = 0→19
Tmin = 0.928, Tmax = 0.969	l = 0→18
3556 measured reflections	3 standard reflections every 200 reflections
3556 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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.194	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.09P)^2] where P = (Fo^2 + 2Fc^2)/3
3556 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq
F1	0.7190 (4)	0.0100 (2)	0.4820 (2)	0.1420 (12)
O1	0.9867 (3)	0.24187 (15)	0.71760 (14)	0.0633 (7)
O2	0.7856 (3)	0.44958 (15)	0.69072 (16)	0.0714 (7)
N1	0.6977 (3)	0.33435 (18)	0.76973 (16)	0.0571 (7)
H1A	0.7233	0.2831	0.7860	0.068*
C1	0.7831 (6)	0.0689 (3)	0.5403 (3)	0.0916 (14)
C2	0.8676 (6)	0.0405 (3)	0.6145 (3)	0.0906 (13)
H2A	0.8810	−0.0177	0.6254	0.109*
C3	0.9319 (5)	0.1008 (2)	0.6723 (3)	0.0718 (11)
H3A	0.9873	0.0830	0.7234	0.086*
C4	0.9151 (4)	0.1874 (2)	0.6552 (2)	0.0561 (9)
C5	0.8302 (5)	0.2139 (3)	0.5798 (2)	0.0685 (10)
H5A	0.8161	0.2720	0.5683	0.082*
C6	0.7662 (5)	0.1535 (3)	0.5217 (2)	0.0839 (13)
H6A	0.7118	0.1708	0.4702	0.101*
C7	0.9846 (4)	0.3310 (2)	0.7002 (2)	0.0650 (10)
H7A	1.0128	0.3397	0.6391	0.078*
H7B	1.0765	0.3579	0.7346	0.078*
C8	0.8097 (4)	0.3763 (2)	0.7198 (2)	0.0532 (8)
C9	0.5318 (5)	0.3721 (2)	0.7982 (2)	0.0702 (10)
H9A	0.4688	0.3316	0.8334	0.105*
H9B	0.4622	0.3870	0.7480	0.105*
H9C	0.5553	0.4227	0.8320	0.105*
F2	0.1365 (3)	0.17462 (14)	0.40790 (15)	0.0873 (7)
O3	0.3832 (3)	0.45673 (14)	0.58358 (14)	0.0611 (6)
O4	0.3031 (3)	0.67419 (16)	0.64043 (16)	0.0712 (7)
N2	0.4978 (3)	0.57710 (18)	0.69226 (17)	0.0578 (7)
H2B	0.5391	0.5262	0.6866	0.069*
C10	0.1956 (5)	0.2462 (2)	0.4502 (2)	0.0585 (9)
C11	0.3168 (5)	0.2360 (2)	0.5167 (2)	0.0625 (9)
H11A	0.3572	0.1819	0.5324	0.075*
C12	0.3758 (5)	0.3077 (2)	0.5590 (2)	0.0586 (9)
H12A	0.4580	0.3021	0.6037	0.070*
C13	0.3159 (4)	0.3882 (2)	0.53679 (19)	0.0487 (8)
C14	0.1940 (4)	0.3972 (2)	0.46881 (19)	0.0537 (8)
H14A	0.1537	0.4511	0.4524	0.064*
C15	0.1345 (4)	0.3246 (2)	0.4264 (2)	0.0605 (9)
H15A	0.0524	0.3294	0.3815	0.073*
C16	0.3009 (4)	0.5382 (2)	0.5739 (2)	0.0549 (8)
H16A	0.1751	0.5320	0.5817	0.066*
H16B	0.3211	0.5594	0.5152	0.066*
C17	0.3705 (4)	0.6021 (2)	0.6389 (2)	0.0532 (8)
C18	0.5712 (5)	0.6320 (2)	0.7601 (2)	0.0732 (11)
H18A	0.6623	0.6017	0.7908	0.110*
H18B	0.4802	0.6478	0.8004	0.110*
H18C	0.6195	0.6826	0.7340	0.110*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.150 (3)	0.147 (3)	0.128 (2)	0.006 (2)	−0.036 (2)	−0.058 (2)
O1	0.0614 (15)	0.0634 (16)	0.0652 (14)	0.0081 (12)	−0.0061 (12)	0.0062 (12)
O2	0.0737 (16)	0.0606 (15)	0.0799 (16)	0.0061 (13)	0.0080 (13)	0.0232 (13)
N1	0.0578 (17)	0.0590 (17)	0.0544 (15)	0.0046 (14)	0.0055 (14)	0.0116 (13)
C1	0.088 (3)	0.099 (4)	0.088 (3)	0.005 (3)	−0.007 (3)	−0.031 (3)
C2	0.101 (3)	0.072 (3)	0.098 (3)	0.008 (3)	−0.004 (3)	−0.008 (3)
C3	0.074 (3)	0.071 (3)	0.070 (2)	0.010 (2)	−0.005 (2)	0.008 (2)
C4	0.0452 (18)	0.069 (2)	0.0536 (18)	0.0077 (17)	0.0050 (16)	0.0067 (17)
C5	0.061 (2)	0.083 (3)	0.061 (2)	0.015 (2)	0.0049 (19)	0.009 (2)
C6	0.077 (3)	0.117 (4)	0.057 (2)	0.013 (3)	−0.010 (2)	−0.006 (2)
C7	0.054 (2)	0.071 (3)	0.070 (2)	−0.0001 (18)	−0.0013 (18)	0.0089 (19)
C8	0.0518 (19)	0.058 (2)	0.0503 (17)	−0.0016 (16)	−0.0016 (16)	0.0051 (16)
C9	0.065 (2)	0.085 (3)	0.061 (2)	0.011 (2)	0.0103 (19)	0.0112 (19)
F2	0.0951 (16)	0.0712 (14)	0.0954 (16)	−0.0074 (12)	−0.0110 (13)	−0.0246 (12)
O3	0.0623 (14)	0.0591 (14)	0.0619 (14)	0.0113 (12)	−0.0176 (11)	−0.0135 (11)
O4	0.0731 (16)	0.0591 (15)	0.0812 (16)	0.0155 (13)	−0.0151 (13)	−0.0187 (13)
N2	0.0569 (17)	0.0600 (17)	0.0564 (16)	0.0036 (14)	−0.0042 (14)	−0.0116 (14)
C10	0.061 (2)	0.056 (2)	0.059 (2)	−0.0063 (17)	0.0036 (17)	−0.0172 (17)
C11	0.073 (2)	0.052 (2)	0.063 (2)	0.0102 (18)	−0.0005 (19)	−0.0026 (17)
C12	0.066 (2)	0.061 (2)	0.0492 (17)	0.0107 (18)	−0.0070 (16)	−0.0010 (17)
C13	0.0486 (18)	0.056 (2)	0.0411 (16)	0.0002 (16)	0.0014 (15)	−0.0073 (15)
C14	0.054 (2)	0.059 (2)	0.0476 (17)	0.0014 (16)	−0.0039 (16)	−0.0022 (16)
C15	0.058 (2)	0.070 (2)	0.0531 (19)	0.0010 (18)	−0.0085 (16)	−0.0088 (18)
C16	0.0548 (19)	0.052 (2)	0.0578 (19)	0.0064 (16)	−0.0045 (16)	−0.0082 (16)
C17	0.0466 (18)	0.059 (2)	0.0541 (18)	0.0012 (16)	0.0010 (16)	−0.0105 (16)
C18	0.068 (2)	0.081 (3)	0.070 (2)	0.005 (2)	−0.017 (2)	−0.019 (2)

Geometric parameters (Å, º)

F1—C1	1.370 (5)	F2—C10	1.368 (4)
O1—C4	1.390 (4)	O3—C13	1.385 (4)
O1—C7	1.417 (4)	O3—C16	1.427 (4)
O2—C8	1.242 (4)	O4—C17	1.238 (4)
N1—C8	1.321 (4)	N2—C17	1.324 (4)
N1—C9	1.461 (4)	N2—C18	1.457 (4)
N1—H1A	0.8600	N2—H2B	0.8600
C1—C6	1.358 (6)	C10—C15	1.359 (5)
C1—C2	1.377 (6)	C10—C11	1.381 (5)
C2—C3	1.381 (6)	C11—C12	1.369 (4)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.384 (5)	C12—C13	1.380 (4)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.384 (5)	C13—C14	1.399 (4)
C5—C6	1.384 (5)	C14—C15	1.383 (4)
C5—H5A	0.9300	C14—H14A	0.9300
C6—H6A	0.9300	C15—H15A	0.9300
C7—C8	1.537 (5)	C16—C17	1.504 (4)
C7—H7A	0.9700	C16—H16A	0.9700
C7—H7B	0.9700	C16—H16B	0.9700
C9—H9A	0.9600	C18—H18A	0.9600
C9—H9B	0.9600	C18—H18B	0.9600
C9—H9C	0.9600	C18—H18C	0.9600
C4—O1—C7	117.9 (3)	C13—O3—C16	118.3 (2)
C8—N1—C9	122.1 (3)	C17—N2—C18	123.0 (3)
C8—N1—H1A	118.9	C17—N2—H2B	118.5
C9—N1—H1A	118.9	C18—N2—H2B	118.5
C6—C1—F1	118.9 (5)	C15—C10—F2	119.8 (3)
C6—C1—C2	122.0 (4)	C15—C10—C11	121.9 (3)
F1—C1—C2	119.0 (5)	F2—C10—C11	118.2 (3)
C1—C2—C3	118.1 (4)	C12—C11—C10	118.1 (3)
C1—C2—H2A	120.9	C12—C11—H11A	120.9
C3—C2—H2A	120.9	C10—C11—H11A	120.9
C2—C3—C4	120.9 (4)	C11—C12—C13	121.5 (3)
C2—C3—H3A	119.5	C11—C12—H12A	119.3
C4—C3—H3A	119.5	C13—C12—H12A	119.3
C3—C4—C5	119.6 (4)	C12—C13—O3	117.1 (3)
C3—C4—O1	115.7 (3)	C12—C13—C14	119.5 (3)
C5—C4—O1	124.8 (3)	O3—C13—C14	123.4 (3)
C6—C5—C4	119.6 (4)	C15—C14—C13	118.8 (3)
C6—C5—H5A	120.2	C15—C14—H14A	120.6
C4—C5—H5A	120.2	C13—C14—H14A	120.6
C1—C6—C5	119.8 (4)	C10—C15—C14	120.1 (3)
C1—C6—H6A	120.1	C10—C15—H15A	119.9
C5—C6—H6A	120.1	C14—C15—H15A	119.9
O1—C7—C8	115.1 (3)	O3—C16—C17	111.7 (3)
O1—C7—H7A	108.5	O3—C16—H16A	109.3
C8—C7—H7A	108.5	C17—C16—H16A	109.3
O1—C7—H7B	108.5	O3—C16—H16B	109.3
C8—C7—H7B	108.5	C17—C16—H16B	109.3
H7A—C7—H7B	107.5	H16A—C16—H16B	107.9
O2—C8—N1	124.7 (3)	O4—C17—N2	124.0 (3)
O2—C8—C7	118.8 (3)	O4—C17—C16	118.1 (3)
N1—C8—C7	116.4 (3)	N2—C17—C16	117.9 (3)
N1—C9—H9A	109.5	N2—C18—H18A	109.5
N1—C9—H9B	109.5	N2—C18—H18B	109.5
H9A—C9—H9B	109.5	H18A—C18—H18B	109.5
N1—C9—H9C	109.5	N2—C18—H18C	109.5
H9A—C9—H9C	109.5	H18A—C18—H18C	109.5
H9B—C9—H9C	109.5	H18B—C18—H18C	109.5
C6—C1—C2—C3	1.8 (7)	C15—C10—C11—C12	−0.1 (5)
F1—C1—C2—C3	179.7 (4)	F2—C10—C11—C12	−180.0 (3)
C1—C2—C3—C4	−1.3 (6)	C10—C11—C12—C13	0.4 (5)
C2—C3—C4—C5	1.1 (5)	C11—C12—C13—O3	179.8 (3)
C2—C3—C4—O1	−179.3 (3)	C11—C12—C13—C14	−0.9 (5)
C7—O1—C4—C3	175.4 (3)	C16—O3—C13—C12	−168.4 (3)
C7—O1—C4—C5	−5.0 (4)	C16—O3—C13—C14	12.4 (4)
C3—C4—C5—C6	−1.3 (5)	C12—C13—C14—C15	1.0 (5)
O1—C4—C5—C6	179.1 (3)	O3—C13—C14—C15	−179.8 (3)
F1—C1—C6—C5	−180.0 (4)	F2—C10—C15—C14	−179.9 (3)
C2—C1—C6—C5	−2.1 (7)	C11—C10—C15—C14	0.3 (5)
C4—C5—C6—C1	1.8 (6)	C13—C14—C15—C10	−0.7 (5)
C4—O1—C7—C8	81.4 (4)	C13—O3—C16—C17	171.1 (2)
C9—N1—C8—O2	−1.6 (5)	C18—N2—C17—O4	1.0 (5)
C9—N1—C8—C7	175.9 (3)	C18—N2—C17—C16	−177.6 (3)
O1—C7—C8—O2	−166.0 (3)	O3—C16—C17—O4	−176.2 (3)
O1—C7—C8—N1	16.3 (4)	O3—C16—C17—N2	2.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	2.35	2.751 (3)	109
N1—H1A···O4^i	0.86	2.05	2.855 (4)	155
N2—H2B···O2	0.86	2.23	2.960 (3)	143
N2—H2B···O3	0.86	2.25	2.656 (3)	109
C2—H2A···F2^ii	0.93	2.51	3.378 (5)	156

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, −y, −z+1.