2-(9H-Fluoren-9-yl)-4-(4-fluoro-anilino)-4-oxo-butanoic acid.

In the title compound, C23H18FNO3, the tricyclic 9-fluorenyl system is approximately planar (r.m.s. deviation = 0.0279 Å). The N-C(=O) bond length is comparatively short [1.359 (3) Å], which is typical for such conjugated systems. The N atom has a planar configuration [sum of bond angles= 359.8°] due to conjugation of its lone pair with the π-system of the carbonyl group. In the crystal, a three-dimensional network is formed through N-H⋯O and O-H⋯O hydrogen bonds between the amide and carb-oxy-lic acid groups and carbonyl O-atom acceptors.

Related literature

For the synthesis of various succinic anhydrides, see: Clar (1942 ▶). For biological studies on substituted succinimides, see: Carroll et al. (2007 ▶); Miller & Johns (1951 ▶); Patsalos (2005 ▶); Rankin et al. (1986 ▶). For the synthesis of substituted phenysuccinamic acids, see: Galustyan et al. (2000 ▶); Stephani et al. (2002 ▶).

Experimental

Crystal data

C23H18FNO3

M = 375.38

Monoclinic,

a = 10.2048 (6) Å

b = 18.5170 (11) Å

c = 9.6164 (6) Å

β = 90.494 (4)°

V = 1817.07 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.45 × 0.10 × 0.03 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: numerical (SADABS; Bruker, 2008 ▶) T min = 0.957, T max = 0.997

8408 measured reflections

3205 independent reflections

1744 reflections with I > 2σ(I)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.104

S = 1.00

3205 reflections

261 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813013779/mw2107sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013779/mw2107Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813013779/mw2107Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H18FNO3	F(000) = 784
Mr = 375.38	Dx = 1.372 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.2048 (6) Å	Cell parameters from 8408 reflections
b = 18.5170 (11) Å	θ = 2.3–25.0°
c = 9.6164 (6) Å	µ = 0.10 mm−1
β = 90.494 (4)°	T = 296 K
V = 1817.07 (19) Å3	Plate, colourless
Z = 4	0.45 × 0.10 × 0.03 mm

Bruker SMART APEXII CCD area-detector diffractometer	3205 independent reflections
Radiation source: fine-focus sealed tube	1744 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.081
ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: numerical (SADABS; Bruker, 2008)	h = −12→11
Tmin = 0.957, Tmax = 0.997	k = −22→19
8408 measured reflections	l = −11→11

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.027P)2] where P = (Fo2 + 2Fc2)/3
3205 reflections	(Δ/σ)max < 0.001
261 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq
C18	0.0042 (3)	0.33919 (14)	0.9353 (3)	0.0216 (7)
C14	0.2656 (2)	0.11015 (14)	0.9369 (3)	0.0202 (7)
H14	0.2753	0.1104	0.8356	0.024*
C15	0.1482 (3)	0.06320 (16)	0.9696 (3)	0.0229 (7)
C17	0.1516 (3)	0.23277 (15)	0.8999 (3)	0.0203 (7)
C13	0.3918 (2)	0.07796 (15)	0.9989 (3)	0.0214 (7)
H13	0.3919	0.0254	0.9864	0.026*
C11	0.5535 (3)	0.10772 (16)	0.7975 (3)	0.0319 (8)
H11	0.5028	0.0842	0.7306	0.038*
C19	−0.0347 (3)	0.35150 (16)	0.7993 (3)	0.0296 (8)
H19	−0.0054	0.3213	0.7288	0.035*
C7	0.5909 (3)	0.14513 (15)	1.0345 (3)	0.0259 (7)
C20	−0.1172 (3)	0.40861 (16)	0.7674 (3)	0.0323 (8)
H20	−0.1438	0.4170	0.6761	0.039*
C2	0.3348 (3)	0.08065 (16)	1.2646 (3)	0.0330 (8)
H2	0.2598	0.0526	1.2538	0.040*
C4	0.4815 (3)	0.14928 (17)	1.4117 (3)	0.0413 (9)
H4	0.5029	0.1676	1.4990	0.050*
C1	0.4133 (3)	0.09618 (15)	1.1518 (3)	0.0236 (7)
C16	0.2473 (3)	0.18896 (14)	0.9832 (3)	0.0202 (7)
H16A	0.2193	0.1889	1.0794	0.024*
H16B	0.3319	0.2128	0.9802	0.024*
C12	0.5141 (3)	0.11031 (14)	0.9341 (3)	0.0231 (7)
C23	−0.0407 (3)	0.38466 (16)	1.0388 (3)	0.0341 (8)
H23	−0.0158	0.3766	1.1308	0.041*
C21	−0.1584 (3)	0.45197 (17)	0.8716 (4)	0.0379 (9)
C3	0.3702 (3)	0.10780 (17)	1.3944 (3)	0.0399 (9)
H3	0.3180	0.0978	1.4708	0.048*
C8	0.7078 (3)	0.17802 (16)	0.9971 (3)	0.0346 (8)
H8	0.7591	0.2017	1.0633	0.042*
C9	0.7465 (3)	0.17492 (17)	0.8601 (4)	0.0403 (9)
H9	0.8251	0.1962	0.8342	0.048*
C6	0.5273 (3)	0.13700 (15)	1.1689 (3)	0.0280 (8)
C22	−0.1219 (3)	0.44173 (17)	1.0068 (3)	0.0441 (10)
H22	−0.1514	0.4727	1.0760	0.053*
C10	0.6708 (3)	0.14094 (17)	0.7615 (3)	0.0408 (9)
H10	0.6980	0.1401	0.6695	0.049*
C5	0.5615 (3)	0.16381 (16)	1.2995 (3)	0.0371 (9)
H5	0.6373	0.1912	1.3112	0.045*
O3	0.13680 (18)	0.22640 (10)	0.77394 (19)	0.0278 (5)
O2	0.15591 (18)	0.00507 (11)	1.0272 (2)	0.0308 (5)
O1	0.0355 (2)	0.09099 (11)	0.9269 (2)	0.0361 (6)
N1	0.0878 (2)	0.28259 (13)	0.9779 (2)	0.0206 (6)
F1	−0.23954 (19)	0.50859 (10)	0.83812 (19)	0.0604 (6)
H1O	−0.038 (3)	0.0582 (18)	0.943 (3)	0.086 (13)*
H1N	0.106 (2)	0.2840 (13)	1.067 (3)	0.025 (8)*

	U11	U22	U33	U12	U13	U23
C18	0.0223 (17)	0.0195 (18)	0.0232 (17)	0.0001 (14)	0.0031 (14)	0.0025 (14)
C14	0.0212 (17)	0.0185 (17)	0.0208 (16)	−0.0012 (13)	−0.0029 (13)	−0.0015 (13)
C15	0.0235 (18)	0.0241 (19)	0.0212 (16)	−0.0002 (15)	−0.0008 (14)	−0.0043 (15)
C17	0.0206 (17)	0.0203 (18)	0.0201 (17)	−0.0037 (14)	−0.0002 (14)	0.0041 (14)
C13	0.0202 (17)	0.0189 (17)	0.0249 (17)	−0.0007 (13)	−0.0062 (14)	0.0026 (14)
C11	0.0275 (19)	0.033 (2)	0.035 (2)	0.0073 (16)	−0.0026 (16)	0.0010 (16)
C19	0.0331 (19)	0.0319 (19)	0.0236 (18)	0.0101 (16)	−0.0028 (15)	0.0008 (15)
C7	0.0214 (17)	0.0211 (18)	0.0350 (19)	0.0025 (14)	−0.0050 (16)	0.0035 (15)
C20	0.036 (2)	0.034 (2)	0.0263 (18)	0.0095 (17)	−0.0052 (16)	0.0077 (16)
C2	0.0294 (19)	0.036 (2)	0.0334 (19)	−0.0054 (16)	−0.0049 (16)	0.0091 (16)
C4	0.052 (2)	0.043 (2)	0.028 (2)	0.0059 (19)	−0.0134 (19)	−0.0004 (17)
C1	0.0211 (17)	0.0223 (18)	0.0275 (18)	0.0015 (14)	−0.0009 (15)	0.0063 (14)
C16	0.0191 (17)	0.0213 (17)	0.0203 (16)	0.0005 (13)	−0.0008 (13)	−0.0002 (13)
C12	0.0201 (17)	0.0206 (17)	0.0285 (18)	0.0032 (13)	0.0008 (15)	0.0071 (14)
C23	0.050 (2)	0.032 (2)	0.0201 (17)	0.0133 (17)	0.0068 (16)	0.0042 (15)
C21	0.035 (2)	0.030 (2)	0.048 (2)	0.0173 (17)	0.0076 (18)	0.0156 (18)
C3	0.040 (2)	0.053 (2)	0.027 (2)	−0.0014 (18)	−0.0026 (17)	0.0085 (17)
C8	0.0218 (18)	0.036 (2)	0.045 (2)	−0.0044 (15)	−0.0080 (17)	0.0117 (17)
C9	0.0217 (19)	0.044 (2)	0.055 (2)	−0.0021 (16)	0.0040 (19)	0.0211 (19)
C6	0.0289 (19)	0.0236 (19)	0.0316 (19)	0.0000 (15)	−0.0056 (16)	0.0029 (15)
C22	0.066 (3)	0.036 (2)	0.031 (2)	0.0247 (19)	0.0153 (19)	0.0060 (17)
C10	0.033 (2)	0.049 (2)	0.040 (2)	0.0059 (18)	0.0094 (18)	0.0125 (19)
C5	0.033 (2)	0.038 (2)	0.040 (2)	−0.0025 (16)	−0.0096 (18)	0.0042 (17)
O3	0.0411 (14)	0.0281 (12)	0.0141 (11)	0.0038 (10)	−0.0010 (10)	−0.0011 (10)
O2	0.0260 (13)	0.0231 (13)	0.0430 (13)	−0.0037 (10)	−0.0082 (10)	0.0084 (11)
O1	0.0187 (12)	0.0319 (14)	0.0576 (15)	−0.0008 (11)	−0.0042 (11)	0.0148 (11)
N1	0.0266 (15)	0.0235 (15)	0.0116 (14)	0.0062 (12)	−0.0018 (12)	0.0010 (12)
F1	0.0747 (16)	0.0495 (13)	0.0572 (13)	0.0380 (11)	0.0059 (12)	0.0156 (11)

C18—C19	1.383 (4)	C2—C1	1.385 (4)
C18—C23	1.385 (4)	C2—C3	1.390 (4)
C18—N1	1.410 (3)	C2—H2	0.9300
C14—C15	1.516 (3)	C4—C3	1.380 (4)
C14—C13	1.535 (3)	C4—C5	1.385 (4)
C14—C16	1.538 (3)	C4—H4	0.9300
C14—H14	0.9800	C1—C6	1.396 (4)
C15—O2	1.212 (3)	C16—H16A	0.9700
C15—O1	1.322 (3)	C16—H16B	0.9700
C17—O3	1.225 (3)	C23—C22	1.377 (4)
C17—N1	1.359 (3)	C23—H23	0.9300
C17—C16	1.497 (4)	C21—C22	1.362 (4)
C13—C1	1.522 (4)	C21—F1	1.373 (3)
C13—C12	1.522 (3)	C3—H3	0.9300
C13—H13	0.9800	C8—C9	1.380 (4)
C11—C12	1.378 (4)	C8—H8	0.9300
C11—C10	1.391 (4)	C9—C10	1.371 (4)
C11—H11	0.9300	C9—H9	0.9300
C19—C20	1.384 (4)	C6—C5	1.392 (4)
C19—H19	0.9300	C22—H22	0.9300
C7—C8	1.390 (4)	C10—H10	0.9300
C7—C12	1.396 (4)	C5—H5	0.9300
C7—C6	1.458 (4)	O1—H1O	0.98 (4)
C20—C21	1.353 (4)	N1—H1N	0.88 (2)
C20—H20	0.9300
C19—C18—C23	119.1 (3)	C6—C1—C13	110.3 (2)
C19—C18—N1	124.5 (3)	C17—C16—C14	116.1 (2)
C23—C18—N1	116.5 (3)	C17—C16—H16A	108.3
C15—C14—C13	111.0 (2)	C14—C16—H16A	108.3
C15—C14—C16	112.7 (2)	C17—C16—H16B	108.3
C13—C14—C16	111.1 (2)	C14—C16—H16B	108.3
C15—C14—H14	107.3	H16A—C16—H16B	107.4
C13—C14—H14	107.3	C11—C12—C7	120.6 (3)
C16—C14—H14	107.3	C11—C12—C13	128.6 (3)
O2—C15—O1	122.7 (3)	C7—C12—C13	110.8 (2)
O2—C15—C14	123.8 (3)	C22—C23—C18	120.5 (3)
O1—C15—C14	113.5 (3)	C22—C23—H23	119.7
O3—C17—N1	123.8 (3)	C18—C23—H23	119.7
O3—C17—C16	123.5 (3)	C20—C21—C22	122.7 (3)
N1—C17—C16	112.7 (2)	C20—C21—F1	118.0 (3)
C1—C13—C12	101.3 (2)	C22—C21—F1	119.3 (3)
C1—C13—C14	113.7 (2)	C4—C3—C2	121.1 (3)
C12—C13—C14	112.1 (2)	C4—C3—H3	119.4
C1—C13—H13	109.8	C2—C3—H3	119.4
C12—C13—H13	109.8	C9—C8—C7	118.8 (3)
C14—C13—H13	109.8	C9—C8—H8	120.6
C12—C11—C10	118.7 (3)	C7—C8—H8	120.6
C12—C11—H11	120.7	C10—C9—C8	121.0 (3)
C10—C11—H11	120.7	C10—C9—H9	119.5
C18—C19—C20	120.3 (3)	C8—C9—H9	119.5
C18—C19—H19	119.9	C5—C6—C1	120.1 (3)
C20—C19—H19	119.9	C5—C6—C7	130.7 (3)
C8—C7—C12	120.1 (3)	C1—C6—C7	109.2 (3)
C8—C7—C6	131.6 (3)	C21—C22—C23	118.6 (3)
C12—C7—C6	108.3 (3)	C21—C22—H22	120.7
C21—C20—C19	118.8 (3)	C23—C22—H22	120.7
C21—C20—H20	120.6	C9—C10—C11	120.8 (3)
C19—C20—H20	120.6	C9—C10—H10	119.6
C1—C2—C3	118.7 (3)	C11—C10—H10	119.6
C1—C2—H2	120.6	C4—C5—C6	119.2 (3)
C3—C2—H2	120.6	C4—C5—H5	120.4
C3—C4—C5	120.3 (3)	C6—C5—H5	120.4
C3—C4—H4	119.9	C15—O1—H1O	112 (2)
C5—C4—H4	119.9	C17—N1—C18	129.5 (2)
C2—C1—C6	120.5 (3)	C17—N1—H1N	117.8 (17)
C2—C1—C13	129.2 (3)	C18—N1—H1N	112.5 (17)
C13—C14—C15—O2	−5.7 (4)	C14—C13—C12—C7	119.0 (3)
C16—C14—C15—O2	−131.0 (3)	C19—C18—C23—C22	−0.6 (5)
C13—C14—C15—O1	175.6 (2)	N1—C18—C23—C22	179.5 (3)
C16—C14—C15—O1	50.3 (3)	C19—C20—C21—C22	0.0 (5)
C15—C14—C13—C1	−82.6 (3)	C19—C20—C21—F1	179.7 (3)
C16—C14—C13—C1	43.7 (3)	C5—C4—C3—C2	−0.9 (5)
C15—C14—C13—C12	163.2 (2)	C1—C2—C3—C4	−0.2 (5)
C16—C14—C13—C12	−70.6 (3)	C12—C7—C8—C9	−0.6 (4)
C23—C18—C19—C20	0.2 (4)	C6—C7—C8—C9	177.5 (3)
N1—C18—C19—C20	−180.0 (3)	C7—C8—C9—C10	0.8 (5)
C18—C19—C20—C21	0.2 (5)	C2—C1—C6—C5	−1.4 (4)
C3—C2—C1—C6	1.4 (4)	C13—C1—C6—C5	175.8 (3)
C3—C2—C1—C13	−175.2 (3)	C2—C1—C6—C7	179.9 (3)
C12—C13—C1—C2	−179.8 (3)	C13—C1—C6—C7	−2.9 (3)
C14—C13—C1—C2	59.7 (4)	C8—C7—C6—C5	4.4 (5)
C12—C13—C1—C6	3.3 (3)	C12—C7—C6—C5	−177.4 (3)
C14—C13—C1—C6	−117.1 (3)	C8—C7—C6—C1	−177.1 (3)
O3—C17—C16—C14	−36.1 (4)	C12—C7—C6—C1	1.1 (3)
N1—C17—C16—C14	147.0 (2)	C20—C21—C22—C23	−0.5 (5)
C15—C14—C16—C17	−71.6 (3)	F1—C21—C22—C23	179.9 (3)
C13—C14—C16—C17	163.1 (2)	C18—C23—C22—C21	0.8 (5)
C10—C11—C12—C7	−0.5 (4)	C8—C9—C10—C11	−0.9 (5)
C10—C11—C12—C13	−179.5 (3)	C12—C11—C10—C9	0.7 (5)
C8—C7—C12—C11	0.4 (4)	C3—C4—C5—C6	0.9 (5)
C6—C7—C12—C11	−178.1 (3)	C1—C6—C5—C4	0.2 (4)
C8—C7—C12—C13	179.6 (2)	C7—C6—C5—C4	178.6 (3)
C6—C7—C12—C13	1.1 (3)	O3—C17—N1—C18	−5.9 (5)
C1—C13—C12—C11	176.4 (3)	C16—C17—N1—C18	171.1 (3)
C14—C13—C12—C11	−61.9 (4)	C19—C18—N1—C17	4.0 (5)
C1—C13—C12—C7	−2.6 (3)	C23—C18—N1—C17	−176.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2i	0.98 (4)	1.71 (4)	2.682 (3)	175 (3)
N1—H1N···O3ii	0.88 (2)	2.02 (3)	2.891 (3)	172 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O2i	0.98 (4)	1.71 (4)	2.682 (3)	175 (3)
N1—H1N⋯O3ii	0.88 (2)	2.02 (3)	2.891 (3)	172 (2)

Symmetry codes: (i) ; (ii) .