(9H-Fluoren-9-yl)(phen-yl)phosphinic acid.

The crystal structure of the title compound, C19H15O2P, features pairs of mol-ecules joined by O-H⋯O hydrogen bonds across crystallographic inversion centers. In addition, π-π inter-actions, with a centroid-centroid distance of 3.6273 (9) Å between the fluorene ring systems, connect the dimers into chains along [01-1]. The three rings make dihedral angles of 1.34 (9), 1.52 (10) and 1.51 (7)° with each other.

Related literature

For related structues, see: Burrow et al. (2000 ▶); Vioux et al. (2004 ▶); Siqueira et al. (2006 ▶); Burrow & Siqueira da Silva (2011a ▶,b ▶); Burrow & Siqueira da Silva (2012 ▶). For a description of the Cambridge Structural Database and geometry checks using Mogul, see: Allen (2002 ▶); Bruno et al. (2004 ▶). For hydrogen-bond information, see: Jeffrey (1997 ▶). For the synthesis, see: Boyd & Regan (1994 ▶).

Experimental

Crystal data

C19H15O2P

M = 306.28

Triclinic,

a = 8.5736 (7) Å

b = 9.5668 (8) Å

c = 9.6750 (7) Å

α = 73.348 (5)°

β = 87.388 (5)°

γ = 83.619 (6)°

V = 755.49 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 100 K

0.28 × 0.13 × 0.07 mm

Data collection

Bruker X8 Kappa APEXII diffractometer

Absorption correction: numerical (SADABS; Bruker, 2012 ▶) T min = 0.941, T max = 0.988

21221 measured reflections

4614 independent reflections

3560 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.112

S = 1.03

4614 reflections

202 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2012 ▶); cell refinement: SAINT (Bruker, 2012 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681204891X/lh5563sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204891X/lh5563Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681204891X/lh5563Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681204891X/lh5563Isup4.cml

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

C19H15O2P	Z = 2
Mr = 306.28	F(000) = 320
Triclinic, P1	Dx = 1.346 Mg m−3
a = 8.5736 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.5668 (8) Å	Cell parameters from 3726 reflections
c = 9.6750 (7) Å	θ = 2.2–29.6°
α = 73.348 (5)°	µ = 0.19 mm−1
β = 87.388 (5)°	T = 100 K
γ = 83.619 (6)°	Block, colourless
V = 755.49 (10) Å3	0.28 × 0.13 × 0.07 mm

Bruker X8 Kappa APEXII diffractometer	4614 independent reflections
Radiation source: sealed ceramic X ray tube, Siemens KFF	3560 reflections with I > 2σ(I)
Graphite crystal monochromator	Rint = 0.047
Detector resolution: 8.3333 pixels mm-1	θmax = 30.6°, θmin = 3.1°
0.5 ° ω & φ scans	h = −12→12
Absorption correction: numerical (SADABS; Bruker, 2012)	k = −13→13
Tmin = 0.941, Tmax = 0.988	l = −13→13
21221 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0492P)2 + 0.2304P] where P = (Fo2 + 2Fc2)/3
4614 reflections	(Δ/σ)max = 0.001
202 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

Experimental. The crystal was cooled to 100 K under a cold nitrogen stream.

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
P1	0.38649 (4)	0.66642 (4)	0.34500 (4)	0.01663 (10)
O1	0.43045 (13)	0.51673 (11)	0.31276 (11)	0.0229 (2)
H1	0.468 (2)	0.446 (2)	0.390 (2)	0.034*
O2	0.46941 (12)	0.68440 (11)	0.47107 (10)	0.0194 (2)
C11	0.17814 (16)	0.68985 (15)	0.37075 (14)	0.0175 (3)
C12	0.11582 (17)	0.78050 (16)	0.45427 (15)	0.0211 (3)
H12	0.1836	0.8302	0.4944	0.025*
C13	−0.04498 (18)	0.79814 (18)	0.47880 (16)	0.0259 (3)
H13	−0.0872	0.8602	0.5353	0.031*
C14	−0.14413 (18)	0.72501 (18)	0.42077 (16)	0.0270 (3)
H14	−0.254	0.7363	0.4386	0.032*
C15	−0.08337 (18)	0.63552 (18)	0.33692 (16)	0.0263 (3)
H15	−0.1517	0.5862	0.297	0.032*
C16	0.07715 (18)	0.61796 (17)	0.31121 (16)	0.0228 (3)
H16	0.1185	0.5571	0.2532	0.027*
C21	0.43723 (16)	0.80119 (15)	0.18013 (14)	0.0169 (3)
H21	0.5521	0.786	0.1589	0.02*
C22	0.39388 (16)	0.95586 (15)	0.18998 (14)	0.0177 (3)
C23	0.44714 (18)	1.02482 (16)	0.28454 (15)	0.0224 (3)
H23	0.5212	0.9741	0.3566	0.027*
C24	0.3897 (2)	1.16927 (18)	0.27144 (17)	0.0272 (3)
H24	0.4249	1.218	0.3353	0.033*
C25	0.2816 (2)	1.24361 (17)	0.16620 (18)	0.0286 (4)
H25	0.2444	1.3428	0.1586	0.034*
C26	0.22646 (19)	1.17511 (17)	0.07137 (17)	0.0251 (3)
H26	0.1517	1.2262	0.0001	0.03*
C27	0.28382 (17)	1.02979 (15)	0.08387 (14)	0.0184 (3)
C28	0.25172 (17)	0.93164 (16)	−0.00072 (14)	0.0190 (3)
C29	0.15364 (18)	0.95394 (19)	−0.11764 (16)	0.0254 (3)
H29	0.0904	1.0443	−0.1533	0.031*
C30	0.15047 (19)	0.8417 (2)	−0.18061 (16)	0.0301 (4)
H30	0.0847	0.8558	−0.2609	0.036*
C31	0.2418 (2)	0.7084 (2)	−0.12883 (17)	0.0298 (4)
H31	0.2379	0.6331	−0.1743	0.036*
C32	0.33901 (19)	0.68459 (17)	−0.01075 (16)	0.0244 (3)
H32	0.4007	0.5934	0.0255	0.029*
C33	0.34340 (17)	0.79710 (16)	0.05227 (14)	0.0183 (3)

	U11	U22	U33	U12	U13	U23
P1	0.01661 (18)	0.01688 (17)	0.01648 (17)	−0.00126 (13)	−0.00200 (12)	−0.00478 (13)
O1	0.0300 (6)	0.0182 (5)	0.0207 (5)	0.0024 (4)	−0.0058 (4)	−0.0071 (4)
O2	0.0200 (5)	0.0194 (5)	0.0196 (5)	−0.0018 (4)	−0.0046 (4)	−0.0060 (4)
C11	0.0177 (7)	0.0192 (6)	0.0148 (6)	−0.0048 (5)	−0.0007 (5)	−0.0024 (5)
C12	0.0193 (7)	0.0264 (7)	0.0186 (6)	−0.0042 (6)	−0.0009 (5)	−0.0073 (5)
C13	0.0205 (7)	0.0342 (8)	0.0222 (7)	−0.0016 (6)	0.0021 (6)	−0.0076 (6)
C14	0.0163 (7)	0.0356 (9)	0.0247 (7)	−0.0047 (6)	0.0000 (6)	−0.0009 (6)
C15	0.0224 (8)	0.0301 (8)	0.0256 (7)	−0.0106 (6)	−0.0053 (6)	−0.0031 (6)
C16	0.0243 (8)	0.0234 (7)	0.0216 (7)	−0.0055 (6)	−0.0033 (6)	−0.0062 (6)
C21	0.0151 (6)	0.0191 (6)	0.0169 (6)	−0.0027 (5)	0.0010 (5)	−0.0054 (5)
C22	0.0175 (7)	0.0186 (6)	0.0174 (6)	−0.0052 (5)	0.0049 (5)	−0.0052 (5)
C23	0.0234 (8)	0.0253 (7)	0.0206 (7)	−0.0090 (6)	0.0033 (5)	−0.0078 (6)
C24	0.0330 (9)	0.0273 (8)	0.0269 (8)	−0.0133 (7)	0.0089 (6)	−0.0144 (6)
C25	0.0331 (9)	0.0199 (7)	0.0339 (8)	−0.0058 (6)	0.0124 (7)	−0.0102 (6)
C26	0.0227 (8)	0.0230 (7)	0.0265 (7)	−0.0005 (6)	0.0061 (6)	−0.0037 (6)
C27	0.0186 (7)	0.0199 (7)	0.0164 (6)	−0.0043 (5)	0.0048 (5)	−0.0048 (5)
C28	0.0179 (7)	0.0239 (7)	0.0149 (6)	−0.0043 (5)	0.0032 (5)	−0.0048 (5)
C29	0.0191 (7)	0.0367 (9)	0.0191 (7)	−0.0033 (6)	0.0010 (5)	−0.0057 (6)
C30	0.0247 (8)	0.0501 (10)	0.0190 (7)	−0.0090 (7)	−0.0006 (6)	−0.0135 (7)
C31	0.0322 (9)	0.0407 (9)	0.0244 (7)	−0.0133 (7)	0.0052 (6)	−0.0188 (7)
C32	0.0266 (8)	0.0264 (8)	0.0232 (7)	−0.0066 (6)	0.0061 (6)	−0.0112 (6)
C33	0.0186 (7)	0.0219 (7)	0.0157 (6)	−0.0052 (5)	0.0031 (5)	−0.0066 (5)

P1—O2	1.4997 (10)	C22—C27	1.403 (2)
P1—O1	1.5541 (11)	C23—C24	1.386 (2)
P1—C11	1.7905 (15)	C23—H23	0.95
P1—C21	1.8108 (14)	C24—C25	1.388 (2)
O1—H1	0.90 (2)	C24—H24	0.95
C11—C12	1.396 (2)	C25—C26	1.396 (2)
C11—C16	1.400 (2)	C25—H25	0.95
C12—C13	1.388 (2)	C26—C27	1.395 (2)
C12—H12	0.95	C26—H26	0.95
C13—C14	1.389 (2)	C27—C28	1.4648 (19)
C13—H13	0.95	C28—C29	1.393 (2)
C14—C15	1.387 (2)	C28—C33	1.404 (2)
C14—H14	0.95	C29—C30	1.381 (2)
C15—C16	1.388 (2)	C29—H29	0.95
C15—H15	0.95	C30—C31	1.392 (3)
C16—H16	0.95	C30—H30	0.95
C21—C22	1.5140 (19)	C31—C32	1.395 (2)
C21—C33	1.5181 (19)	C31—H31	0.95
C21—H21	1.0	C32—C33	1.385 (2)
C22—C23	1.3898 (19)	C32—H32	0.95
O2—P1—O1	114.59 (6)	C24—C23—C22	118.52 (15)
O2—P1—C11	110.59 (6)	C24—C23—H23	120.7
O1—P1—C11	108.24 (6)	C22—C23—H23	120.7
O2—P1—C21	110.70 (6)	C23—C24—C25	120.83 (15)
O1—P1—C21	104.29 (6)	C23—C24—H24	119.6
C11—P1—C21	108.08 (6)	C25—C24—H24	119.6
P1—O1—H1	113.2 (12)	C24—C25—C26	121.12 (15)
C12—C11—C16	119.49 (13)	C24—C25—H25	119.4
C12—C11—P1	118.86 (11)	C26—C25—H25	119.4
C16—C11—P1	121.64 (11)	C27—C26—C25	118.36 (15)
C13—C12—C11	120.14 (14)	C27—C26—H26	120.8
C13—C12—H12	119.9	C25—C26—H26	120.8
C11—C12—H12	119.9	C26—C27—C22	120.10 (14)
C12—C13—C14	119.98 (15)	C26—C27—C28	130.83 (14)
C12—C13—H13	120.0	C22—C27—C28	109.06 (12)
C14—C13—H13	120.0	C29—C28—C33	120.35 (14)
C15—C14—C13	120.26 (14)	C29—C28—C27	130.97 (14)
C15—C14—H14	119.9	C33—C28—C27	108.67 (12)
C13—C14—H14	119.9	C30—C29—C28	118.50 (15)
C14—C15—C16	120.11 (14)	C30—C29—H29	120.7
C14—C15—H15	119.9	C28—C29—H29	120.7
C16—C15—H15	119.9	C29—C30—C31	121.31 (15)
C15—C16—C11	120.00 (14)	C29—C30—H30	119.3
C15—C16—H16	120.0	C31—C30—H30	119.3
C11—C16—H16	120.0	C30—C31—C32	120.56 (15)
C22—C21—C33	102.97 (11)	C30—C31—H31	119.7
C22—C21—P1	111.40 (9)	C32—C31—H31	119.7
C33—C21—P1	112.47 (9)	C33—C32—C31	118.38 (15)
C22—C21—H21	109.9	C33—C32—H32	120.8
C33—C21—H21	109.9	C31—C32—H32	120.8
P1—C21—H21	109.9	C32—C33—C28	120.90 (14)
C23—C22—C27	121.07 (14)	C32—C33—C21	129.44 (14)
C23—C22—C21	129.34 (13)	C28—C33—C21	109.66 (12)
C27—C22—C21	109.59 (12)
O2—P1—C11—C12	28.54 (13)	C23—C24—C25—C26	0.5 (2)
O1—P1—C11—C12	154.83 (11)	C24—C25—C26—C27	−0.6 (2)
C21—P1—C11—C12	−92.78 (12)	C25—C26—C27—C22	0.1 (2)
O2—P1—C11—C16	−150.46 (11)	C25—C26—C27—C28	−178.32 (13)
O1—P1—C11—C16	−24.18 (13)	C23—C22—C27—C26	0.3 (2)
C21—P1—C11—C16	88.21 (13)	C21—C22—C27—C26	−179.72 (12)
C16—C11—C12—C13	0.5 (2)	C23—C22—C27—C28	179.08 (12)
P1—C11—C12—C13	−178.55 (11)	C21—C22—C27—C28	−0.95 (15)
C11—C12—C13—C14	0.3 (2)	C26—C27—C28—C29	−0.6 (3)
C12—C13—C14—C15	−0.7 (2)	C22—C27—C28—C29	−179.21 (14)
C13—C14—C15—C16	0.4 (2)	C26—C27—C28—C33	178.00 (14)
C14—C15—C16—C11	0.4 (2)	C22—C27—C28—C33	−0.60 (15)
C12—C11—C16—C15	−0.8 (2)	C33—C28—C29—C30	−0.8 (2)
P1—C11—C16—C15	178.15 (11)	C27—C28—C29—C30	177.70 (14)
O2—P1—C21—C22	−59.17 (11)	C28—C29—C30—C31	0.4 (2)
O1—P1—C21—C22	177.10 (9)	C29—C30—C31—C32	0.3 (2)
C11—P1—C21—C22	62.09 (11)	C30—C31—C32—C33	−0.7 (2)
O2—P1—C21—C33	−174.18 (9)	C31—C32—C33—C28	0.3 (2)
O1—P1—C21—C33	62.09 (11)	C31—C32—C33—C21	179.97 (13)
C11—P1—C21—C33	−52.93 (11)	C29—C28—C33—C32	0.4 (2)
C33—C21—C22—C23	−178.06 (13)	C27—C28—C33—C32	−178.41 (12)
P1—C21—C22—C23	61.18 (17)	C29—C28—C33—C21	−179.31 (12)
C33—C21—C22—C27	1.98 (14)	C27—C28—C33—C21	1.90 (15)
P1—C21—C22—C27	−118.78 (11)	C22—C21—C33—C32	177.99 (14)
C27—C22—C23—C24	−0.4 (2)	P1—C21—C33—C32	−61.99 (17)
C21—C22—C23—C24	179.68 (13)	C22—C21—C33—C28	−2.36 (14)
C22—C23—C24—C25	−0.1 (2)	P1—C21—C33—C28	117.67 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.90 (2)	1.61 (2)	2.5107 (15)	177.9 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.90 (2)	1.61 (2)	2.5107 (15)	177.9 (19)

Symmetry code: (i) .