A monoclinic polymorph of α-diphenyl­phosphor­yl-o-cresol

When attempting the synthesis of the copper complex of the title compound {systematic name: 2-[(diphenyl­phosphor­yl)­meth­yl]phenol}, C₁₉H₁₇O₂P, a new monoclinic polymorphic modification of the ligand was obtained instead of the complex. The variations of mol­ecular geometry and supramol­ecular organization in the crystal structures of the two polymorphs are discussed.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.040
• wR factor = 0.119
• Data-to-parameter ratio = 16.9

checkCIF/PLATON results

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: PROFIT (Strel'tsov & Zavodnik, 1989); program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1994); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus; software used to prepare material for publication: SHELXTL-Plus.

2-[(diphenylphosphoryl)methyl]phenol

Crystal data

C19H17O2P	F(000) = 648
Mr = 308.30	Dx = 1.312 Mg m^−3
Monoclinic, P21/n	Melting point: 429.0 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.092 (2) Å	Cell parameters from 48 reflections
b = 10.521 (2) Å	θ = 4.2–12.2°
c = 14.699 (3) Å	µ = 0.18 mm^−1
β = 90.43 (3)°	T = 298 K
V = 1560.7 (5) Å^3	Prism, colorless
Z = 4	0.35 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.033
Radiation source: fine-focus sealed tube	θmax = 30.0°, θmin = 2.4°
Graphite monochromator	h = 0→14
ω/2θ scans	k = 0→14
4817 measured reflections	l = −20→20
4519 independent reflections	2 standard reflections every 98 reflections
3352 reflections with I > 2σ(I)	intensity decay: 2%

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)] = 0.040	Hydrogen site location: difference Fourier map
wR(F^2) = 0.119	All H-atom parameters refined
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0705P)^2 + 0.2609P] where P = (Fo^2 + 2Fc^2)/3
4519 reflections	(Δ/σ)max = 0.001
267 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.27 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
P1	0.54374 (3)	0.26801 (3)	0.14859 (2)	0.03072 (11)
O1	0.43072 (10)	0.32461 (11)	0.09655 (7)	0.0385 (2)
O2	0.63300 (11)	0.54052 (11)	0.04973 (7)	0.0405 (2)
H2O	0.612 (2)	0.587 (2)	0.0082 (17)	0.074 (7)*
C1	0.65700 (14)	0.38394 (15)	0.19982 (11)	0.0379 (3)
H2	0.7326 (18)	0.3865 (18)	0.1627 (12)	0.045 (5)*
H1A	0.679 (2)	0.351 (2)	0.2596 (14)	0.056 (5)*
C2	0.59881 (13)	0.51492 (14)	0.20688 (9)	0.0330 (3)
C3	0.58598 (13)	0.58942 (13)	0.12852 (9)	0.0325 (3)
C4	0.53058 (16)	0.71019 (15)	0.13393 (11)	0.0398 (3)
H4	0.5192 (17)	0.7589 (17)	0.0772 (12)	0.038 (4)*
C5	0.49068 (18)	0.75807 (16)	0.21731 (12)	0.0461 (4)
H5	0.4537 (19)	0.843 (2)	0.2205 (13)	0.051 (5)*
C14	0.48213 (13)	0.16999 (13)	0.23957 (9)	0.0313 (3)
C6	0.50678 (17)	0.68697 (18)	0.29543 (12)	0.0464 (4)
H6	0.483 (2)	0.719 (2)	0.3561 (14)	0.056 (6)*
C19	0.56449 (15)	0.12126 (16)	0.30764 (10)	0.0393 (3)
H19	0.6536 (18)	0.1403 (18)	0.3072 (11)	0.042 (5)*
C7	0.55956 (15)	0.56553 (17)	0.28973 (10)	0.0403 (3)
H7	0.5688 (18)	0.5105 (18)	0.3445 (13)	0.043 (5)*
C8	0.64706 (14)	0.16822 (15)	0.07898 (9)	0.0353 (3)
C16	0.29732 (17)	0.05968 (17)	0.30573 (12)	0.0449 (4)
H16	0.208 (2)	0.042 (2)	0.3074 (14)	0.057 (6)*
C15	0.34838 (14)	0.13939 (16)	0.23964 (10)	0.0381 (3)
H15	0.2941 (19)	0.1708 (19)	0.1949 (13)	0.048 (5)*
C18	0.51217 (18)	0.04203 (18)	0.37391 (11)	0.0465 (4)
H18	0.572 (2)	0.011 (2)	0.4166 (15)	0.072 (7)*
C9	0.73272 (18)	0.22591 (19)	0.01746 (12)	0.0489 (4)
H9	0.736 (2)	0.325 (3)	0.0153 (15)	0.068 (6)*
C17	0.37949 (18)	0.01132 (17)	0.37272 (11)	0.0459 (4)
H17	0.343 (2)	−0.043 (2)	0.4181 (14)	0.053 (5)*
C13	0.63801 (18)	0.03653 (17)	0.08029 (12)	0.0478 (4)
H13	0.576 (2)	−0.005 (2)	0.1227 (14)	0.053 (5)*
C10	0.8080 (2)	0.1529 (2)	−0.04071 (13)	0.0584 (5)
H10	0.868 (2)	0.190 (3)	−0.0853 (17)	0.083 (8)*
C12	0.7131 (2)	−0.0360 (2)	0.02158 (16)	0.0635 (5)
H12	0.710 (2)	−0.133 (2)	0.0254 (16)	0.079 (7)*
C11	0.7978 (2)	0.0225 (2)	−0.03846 (14)	0.0601 (5)
H11	0.845 (3)	−0.020 (3)	−0.0789 (18)	0.082 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.02840 (17)	0.03483 (18)	0.02895 (17)	0.00094 (13)	0.00183 (12)	0.00431 (13)
O1	0.0344 (5)	0.0439 (6)	0.0371 (5)	0.0010 (4)	−0.0032 (4)	0.0094 (4)
O2	0.0465 (6)	0.0439 (6)	0.0311 (5)	0.0063 (5)	0.0044 (4)	0.0041 (4)
C1	0.0321 (7)	0.0395 (8)	0.0421 (8)	−0.0013 (6)	−0.0035 (6)	0.0066 (6)
C2	0.0282 (6)	0.0370 (7)	0.0337 (6)	−0.0052 (5)	−0.0009 (5)	0.0014 (5)
C3	0.0296 (6)	0.0352 (7)	0.0326 (6)	−0.0051 (5)	0.0004 (5)	0.0008 (5)
C4	0.0424 (8)	0.0350 (8)	0.0419 (8)	−0.0042 (6)	0.0020 (6)	0.0026 (6)
C5	0.0505 (9)	0.0366 (8)	0.0514 (9)	−0.0040 (7)	0.0059 (7)	−0.0069 (7)
C14	0.0317 (6)	0.0351 (7)	0.0272 (6)	0.0045 (5)	0.0049 (5)	0.0022 (5)
C6	0.0492 (9)	0.0499 (9)	0.0401 (8)	−0.0071 (7)	0.0060 (7)	−0.0103 (7)
C19	0.0323 (7)	0.0495 (9)	0.0361 (7)	0.0081 (6)	0.0025 (5)	0.0060 (6)
C7	0.0388 (7)	0.0498 (9)	0.0323 (7)	−0.0083 (6)	0.0004 (5)	0.0018 (6)
C8	0.0314 (6)	0.0435 (8)	0.0310 (6)	0.0004 (6)	0.0044 (5)	0.0013 (6)
C16	0.0377 (8)	0.0501 (9)	0.0470 (8)	−0.0032 (7)	0.0106 (6)	0.0048 (7)
C15	0.0329 (7)	0.0456 (8)	0.0358 (7)	0.0007 (6)	0.0018 (5)	0.0048 (6)
C18	0.0525 (9)	0.0531 (10)	0.0339 (7)	0.0135 (8)	0.0024 (7)	0.0103 (7)
C9	0.0493 (9)	0.0523 (10)	0.0453 (8)	0.0025 (7)	0.0171 (7)	0.0096 (7)
C17	0.0553 (9)	0.0452 (9)	0.0373 (8)	0.0049 (7)	0.0155 (7)	0.0073 (6)
C13	0.0479 (9)	0.0448 (9)	0.0507 (9)	−0.0096 (7)	0.0171 (7)	−0.0103 (7)
C10	0.0552 (10)	0.0713 (13)	0.0492 (10)	0.0019 (9)	0.0240 (8)	0.0048 (9)
C12	0.0627 (12)	0.0535 (11)	0.0745 (13)	−0.0120 (9)	0.0248 (10)	−0.0254 (10)
C11	0.0526 (10)	0.0737 (13)	0.0542 (11)	−0.0033 (9)	0.0205 (8)	−0.0229 (10)

Geometric parameters (Å, º)

P1—O1	1.4925 (11)	C19—H19	0.921 (18)
P1—C14	1.8031 (14)	C7—H7	0.995 (18)
P1—C8	1.8035 (15)	C8—C13	1.389 (2)
P1—C1	1.8298 (16)	C8—C9	1.395 (2)
O2—C3	1.3561 (17)	C16—C17	1.380 (3)
O2—H2O	0.81 (3)	C16—C15	1.386 (2)
C1—C2	1.502 (2)	C16—H16	0.92 (2)
C1—H2	0.941 (19)	C15—H15	0.914 (19)
C1—H1A	0.97 (2)	C18—C17	1.377 (3)
C2—C7	1.389 (2)	C18—H18	0.93 (2)
C2—C3	1.398 (2)	C9—C10	1.381 (3)
C3—C4	1.391 (2)	C9—H9	1.04 (3)
C4—C5	1.388 (2)	C17—H17	0.96 (2)
C4—H4	0.984 (18)	C13—C12	1.382 (2)
C5—C6	1.379 (3)	C13—H13	0.99 (2)
C5—H5	0.97 (2)	C10—C11	1.377 (3)
C14—C15	1.388 (2)	C10—H10	0.98 (3)
C14—C19	1.394 (2)	C12—C11	1.378 (3)
C6—C7	1.387 (3)	C12—H12	1.02 (3)
C6—H6	0.98 (2)	C11—H11	0.89 (3)
C19—C18	1.389 (2)
O1—P1—C14	109.99 (6)	C6—C7—C2	121.20 (15)
O1—P1—C8	112.60 (7)	C6—C7—H7	121.4 (11)
C14—P1—C8	106.97 (7)	C2—C7—H7	117.4 (11)
O1—P1—C1	114.68 (7)	C13—C8—C9	118.97 (15)
C14—P1—C1	107.09 (7)	C13—C8—P1	122.32 (11)
C8—P1—C1	105.04 (7)	C9—C8—P1	118.57 (13)
C3—O2—H2O	108.6 (17)	C17—C16—C15	119.92 (15)
C2—C1—P1	113.37 (10)	C17—C16—H16	119.3 (13)
C2—C1—H2	109.4 (12)	C15—C16—H16	120.7 (13)
P1—C1—H2	106.7 (11)	C16—C15—C14	120.52 (14)
C2—C1—H1A	110.5 (13)	C16—C15—H15	119.9 (12)
P1—C1—H1A	105.9 (13)	C14—C15—H15	119.6 (12)
H2—C1—H1A	110.9 (17)	C17—C18—C19	120.42 (15)
C7—C2—C3	118.81 (14)	C17—C18—H18	123.6 (14)
C7—C2—C1	121.77 (14)	C19—C18—H18	116.0 (14)
C3—C2—C1	119.41 (13)	C10—C9—C8	120.38 (18)
O2—C3—C4	122.60 (13)	C10—C9—H9	121.3 (12)
O2—C3—C2	117.38 (13)	C8—C9—H9	118.3 (12)
C4—C3—C2	119.99 (13)	C18—C17—C16	120.11 (15)
C5—C4—C3	120.11 (15)	C18—C17—H17	120.8 (12)
C5—C4—H4	121.7 (11)	C16—C17—H17	119.1 (12)
C3—C4—H4	118.1 (11)	C12—C13—C8	120.36 (17)
C6—C5—C4	120.36 (16)	C12—C13—H13	119.9 (13)
C6—C5—H5	120.2 (11)	C8—C13—H13	119.7 (12)
C4—C5—H5	119.4 (11)	C11—C10—C9	119.86 (18)
C15—C14—C19	119.27 (13)	C11—C10—H10	117.5 (16)
C15—C14—P1	118.30 (11)	C9—C10—H10	122.6 (16)
C19—C14—P1	122.40 (11)	C11—C12—C13	119.94 (19)
C5—C6—C7	119.49 (15)	C11—C12—H12	120.0 (14)
C5—C6—H6	122.8 (13)	C13—C12—H12	119.9 (14)
C7—C6—H6	117.7 (13)	C10—C11—C12	120.48 (18)
C18—C19—C14	119.76 (14)	C10—C11—H11	116.5 (17)
C18—C19—H19	120.8 (11)	C12—C11—H11	123.0 (17)
C14—C19—H19	119.5 (11)
O1—P1—C1—C2	17.83 (13)	C3—C2—C7—C6	0.9 (2)
C14—P1—C1—C2	−104.50 (11)	C1—C2—C7—C6	179.56 (14)
C8—P1—C1—C2	142.00 (11)	O1—P1—C8—C13	−101.06 (15)
P1—C1—C2—C7	106.83 (14)	C14—P1—C8—C13	19.89 (16)
P1—C1—C2—C3	−74.49 (15)	C1—P1—C8—C13	133.47 (15)
C7—C2—C3—O2	175.85 (12)	O1—P1—C8—C9	74.65 (14)
C1—C2—C3—O2	−2.87 (19)	C14—P1—C8—C9	−164.41 (13)
C7—C2—C3—C4	−2.2 (2)	C1—P1—C8—C9	−50.82 (14)
C1—C2—C3—C4	179.12 (13)	C17—C16—C15—C14	0.7 (3)
O2—C3—C4—C5	−176.46 (14)	C19—C14—C15—C16	−1.0 (2)
C2—C3—C4—C5	1.4 (2)	P1—C14—C15—C16	177.08 (12)
C3—C4—C5—C6	0.6 (2)	C14—C19—C18—C17	0.0 (3)
O1—P1—C14—C15	12.19 (14)	C13—C8—C9—C10	−0.5 (3)
C8—P1—C14—C15	−110.40 (12)	P1—C8—C9—C10	−176.30 (15)
C1—P1—C14—C15	137.42 (12)	C19—C18—C17—C16	−0.3 (3)
O1—P1—C14—C19	−169.79 (12)	C15—C16—C17—C18	−0.1 (3)
C8—P1—C14—C19	67.62 (14)	C9—C8—C13—C12	0.2 (3)
C1—P1—C14—C19	−44.57 (14)	P1—C8—C13—C12	175.84 (16)
C4—C5—C6—C7	−1.9 (3)	C8—C9—C10—C11	0.4 (3)
C15—C14—C19—C18	0.6 (2)	C8—C13—C12—C11	0.2 (3)
P1—C14—C19—C18	−177.39 (13)	C9—C10—C11—C12	−0.1 (4)
C5—C6—C7—C2	1.2 (2)	C13—C12—C11—C10	−0.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1^i	0.81 (2)	1.84 (3)	2.6513 (16)	172 (2)

Symmetry code: (i) −x+1, −y+1, −z.