N-(2-Fluoro­phen­yl)phthalimide

In the title compound, C₁₄H₈FNO₂, the dihedral angle between the two planar ring systems is 59.95 (4)°.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.037
• wR factor = 0.104
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT301_ALERT_3_C Main Residue  Disorder .........................       5.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C1     -   C2     ...       1.38 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C2     -   C3     ...       1.38 Ang.

   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
   2 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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

N-(2-Fluorophenyl)phthalimide

Crystal data

C14H8FNO2	F(000) = 992
Mr = 241.21	Dx = 1.465 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1794 reflections
a = 11.622 (3) Å	θ = 2.4–22.5°
b = 7.8368 (16) Å	µ = 0.11 mm^−1
c = 24.017 (5) Å	T = 294 K
V = 2187.5 (8) Å^3	Prism, white
Z = 8	0.26 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2240 independent reflections
Radiation source: fine-focus sealed tube	1169 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.066
φ and ω scans	θmax = 26.4°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −13→14
Tmin = 0.967, Tmax = 0.983	k = −7→9
11486 measured reflections	l = −29→29

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0411P)^2 + 0.2748P] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.001
2240 reflections	Δρmax = 0.13 e Å^−3
174 parameters	Δρmin = −0.12 e Å^−3
2 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0218 (14)

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 > 2σ(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)
F1	0.45336 (15)	−0.0205 (2)	0.31890 (7)	0.0741 (7)	0.681 (3)
F1'	0.8064 (3)	0.2372 (5)	0.32862 (16)	0.0722 (16)	0.319 (3)
N1	0.61566 (13)	0.14038 (19)	0.38251 (6)	0.0461 (4)
O1	0.78204 (14)	−0.0051 (2)	0.40639 (6)	0.0779 (5)
O2	0.45026 (12)	0.30430 (19)	0.38866 (6)	0.0658 (5)
C1	0.62486 (17)	0.1271 (2)	0.32346 (8)	0.0459 (5)
C2	0.54049 (18)	0.0479 (3)	0.29278 (9)	0.0540 (6)
H2	0.4761	0.0054	0.3111	0.065*	0.319 (3)
C3	0.5477 (2)	0.0293 (3)	0.23594 (9)	0.0636 (6)
H3	0.4889	−0.0235	0.2160	0.076*
C4	0.6433 (2)	0.0902 (3)	0.20940 (9)	0.0660 (7)
H4	0.6501	0.0774	0.1710	0.079*
C5	0.7294 (2)	0.1700 (3)	0.23856 (9)	0.0664 (6)
H5	0.7940	0.2115	0.2201	0.080*
C6	0.71918 (19)	0.1882 (3)	0.29553 (9)	0.0591 (6)
H6	0.7773	0.2428	0.3153	0.071*	0.681 (3)
C7	0.69670 (18)	0.0731 (3)	0.41974 (8)	0.0498 (5)
C8	0.65634 (16)	0.1192 (2)	0.47600 (8)	0.0443 (5)
C9	0.70264 (18)	0.0835 (3)	0.52747 (9)	0.0553 (6)
H9	0.7694	0.0190	0.5309	0.066*
C10	0.6470 (2)	0.1463 (3)	0.57373 (9)	0.0620 (6)
H10	0.6773	0.1253	0.6089	0.074*
C11	0.54689 (19)	0.2401 (3)	0.56882 (9)	0.0614 (6)
H11	0.5105	0.2802	0.6007	0.074*
C12	0.49990 (17)	0.2751 (3)	0.51708 (9)	0.0562 (6)
H12	0.4325	0.3381	0.5136	0.067*
C13	0.55637 (15)	0.2134 (2)	0.47096 (8)	0.0441 (5)
C14	0.52877 (17)	0.2300 (2)	0.41065 (8)	0.0477 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0669 (13)	0.0951 (15)	0.0602 (12)	−0.0328 (11)	−0.0079 (9)	0.0096 (10)
F1'	0.060 (3)	0.074 (3)	0.082 (3)	−0.016 (2)	0.007 (2)	−0.013 (2)
N1	0.0466 (10)	0.0483 (10)	0.0434 (10)	0.0043 (8)	−0.0088 (8)	0.0000 (8)
O1	0.0755 (12)	0.0902 (12)	0.0681 (10)	0.0404 (10)	−0.0126 (9)	−0.0130 (8)
O2	0.0548 (9)	0.0819 (11)	0.0609 (10)	0.0190 (8)	−0.0058 (7)	0.0129 (8)
C1	0.0483 (12)	0.0437 (12)	0.0457 (12)	0.0021 (10)	−0.0053 (10)	−0.0020 (10)
C2	0.0558 (14)	0.0526 (13)	0.0534 (14)	−0.0077 (11)	−0.0081 (11)	0.0087 (11)
C3	0.0760 (17)	0.0644 (15)	0.0504 (14)	−0.0019 (13)	−0.0174 (13)	−0.0003 (11)
C4	0.0840 (19)	0.0636 (16)	0.0505 (13)	0.0090 (13)	−0.0001 (13)	−0.0001 (12)
C5	0.0707 (16)	0.0647 (15)	0.0637 (16)	0.0013 (12)	0.0156 (13)	−0.0058 (12)
C6	0.0537 (14)	0.0629 (15)	0.0607 (15)	−0.0021 (12)	−0.0038 (12)	−0.0126 (11)
C7	0.0498 (13)	0.0439 (12)	0.0557 (13)	0.0051 (10)	−0.0090 (10)	−0.0036 (10)
C8	0.0437 (11)	0.0433 (11)	0.0459 (12)	−0.0027 (9)	−0.0059 (10)	0.0033 (10)
C9	0.0496 (13)	0.0583 (14)	0.0578 (14)	−0.0016 (10)	−0.0106 (11)	0.0072 (11)
C10	0.0606 (15)	0.0762 (16)	0.0492 (13)	−0.0112 (13)	−0.0063 (11)	0.0086 (12)
C11	0.0619 (15)	0.0749 (16)	0.0473 (14)	−0.0083 (13)	0.0065 (11)	0.0029 (11)
C12	0.0472 (12)	0.0642 (14)	0.0573 (14)	0.0023 (10)	0.0029 (11)	0.0076 (11)
C13	0.0426 (11)	0.0430 (11)	0.0468 (12)	−0.0054 (9)	−0.0029 (9)	0.0058 (9)
C14	0.0415 (12)	0.0467 (12)	0.0548 (13)	−0.0009 (10)	−0.0038 (10)	0.0062 (10)

Geometric parameters (Å, º)

F1—C2	1.307 (2)	C5—C6	1.381 (3)
F1'—C6	1.344 (4)	C5—H5	0.9300
N1—C7	1.402 (2)	C6—H6	0.9300
N1—C14	1.403 (2)	C7—C8	1.475 (3)
N1—C1	1.426 (2)	C8—C9	1.377 (2)
O1—C7	1.209 (2)	C8—C13	1.382 (3)
O2—C14	1.204 (2)	C9—C10	1.377 (3)
C1—C6	1.371 (3)	C9—H9	0.9300
C1—C2	1.374 (3)	C10—C11	1.381 (3)
C2—C3	1.376 (3)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.385 (3)
C3—C4	1.367 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.375 (3)
C4—C5	1.372 (3)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.489 (3)
C7—N1—C14	111.39 (16)	O1—C7—N1	124.94 (19)
C7—N1—C1	123.81 (16)	O1—C7—C8	128.89 (18)
C14—N1—C1	124.71 (15)	N1—C7—C8	106.17 (17)
C6—C1—C2	117.74 (19)	C9—C8—C13	121.05 (18)
C6—C1—N1	121.39 (17)	C9—C8—C7	130.42 (18)
C2—C1—N1	120.85 (18)	C13—C8—C7	108.53 (16)
F1—C2—C1	118.73 (19)	C10—C9—C8	117.91 (19)
F1—C2—C3	118.7 (2)	C10—C9—H9	121.0
C1—C2—C3	122.5 (2)	C8—C9—H9	121.0
C1—C2—H2	118.8	C9—C10—C11	121.2 (2)
C3—C2—H2	118.8	C9—C10—H10	119.4
C4—C3—C2	118.3 (2)	C11—C10—H10	119.4
C4—C3—H3	120.8	C10—C11—C12	120.9 (2)
C2—C3—H3	120.8	C10—C11—H11	119.5
C3—C4—C5	121.0 (2)	C12—C11—H11	119.5
C3—C4—H4	119.5	C13—C12—C11	117.70 (19)
C5—C4—H4	119.5	C13—C12—H12	121.1
C4—C5—C6	119.3 (2)	C11—C12—H12	121.1
C4—C5—H5	120.3	C12—C13—C8	121.23 (18)
C6—C5—H5	120.3	C12—C13—C14	130.53 (18)
F1'—C6—C1	114.4 (2)	C8—C13—C14	108.25 (17)
F1'—C6—C5	123.4 (3)	O2—C14—N1	125.17 (18)
C1—C6—C5	121.2 (2)	O2—C14—C13	129.19 (19)
C1—C6—H6	119.4	N1—C14—C13	105.64 (16)
C5—C6—H6	119.4
C7—N1—C1—C6	−57.3 (3)	N1—C7—C8—C9	179.16 (19)
C14—N1—C1—C6	118.9 (2)	O1—C7—C8—C13	178.1 (2)
C7—N1—C1—C2	120.9 (2)	N1—C7—C8—C13	−1.3 (2)
C14—N1—C1—C2	−62.9 (3)	C13—C8—C9—C10	−0.8 (3)
C6—C1—C2—F1	175.82 (19)	C7—C8—C9—C10	178.8 (2)
N1—C1—C2—F1	−2.4 (3)	C8—C9—C10—C11	1.0 (3)
C6—C1—C2—C3	−0.3 (3)	C9—C10—C11—C12	−0.6 (3)
N1—C1—C2—C3	−178.48 (18)	C10—C11—C12—C13	0.0 (3)
F1—C2—C3—C4	−175.2 (2)	C11—C12—C13—C8	0.2 (3)
C1—C2—C3—C4	0.9 (3)	C11—C12—C13—C14	−179.51 (19)
C2—C3—C4—C5	−0.8 (3)	C9—C8—C13—C12	0.2 (3)
C3—C4—C5—C6	0.3 (3)	C7—C8—C13—C12	−179.45 (17)
C2—C1—C6—F1'	−169.2 (2)	C9—C8—C13—C14	179.96 (17)
N1—C1—C6—F1'	9.1 (3)	C7—C8—C13—C14	0.3 (2)
C2—C1—C6—C5	−0.4 (3)	C7—N1—C14—O2	177.88 (19)
N1—C1—C6—C5	177.86 (19)	C1—N1—C14—O2	1.3 (3)
C4—C5—C6—F1'	168.1 (3)	C7—N1—C14—C13	−1.6 (2)
C4—C5—C6—C1	0.4 (3)	C1—N1—C14—C13	−178.15 (16)
C14—N1—C7—O1	−177.7 (2)	C12—C13—C14—O2	1.1 (3)
C1—N1—C7—O1	−1.1 (3)	C8—C13—C14—O2	−178.7 (2)
C14—N1—C7—C8	1.8 (2)	C12—C13—C14—N1	−179.53 (19)
C1—N1—C7—C8	178.40 (16)	C8—C13—C14—N1	0.7 (2)
O1—C7—C8—C9	−1.4 (4)