Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C19H17O4P, was obtained as colorless block-shaped crystals by the reaction of diphenyl phosphite and benzaldehyde. The crystal structure is stabilized by strong inter­molecular O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680601419X/wk2008sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680601419X/wk2008Isup2.hkl
Contains datablock I

CCDC reference: 608519

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.051
  • wR factor = 0.142
  • Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C8 -C13 1.36 Ang. PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C14 -C19 1.37 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Diphenyl (hydroxyphenylmethyl)phosphonate top
Crystal data top
C19H17O4PF(000) = 712
Mr = 340.30Dx = 1.392 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3127 reflections
a = 10.349 (3) Åθ = 2.4–28.2°
b = 7.881 (2) ŵ = 0.19 mm1
c = 20.362 (6) ÅT = 273 K
β = 102.075 (5)°Block, colorless
V = 1624.0 (8) Å30.29 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker APEX area-detector
diffractometer
2857 independent reflections
Radiation source: fine-focus sealed tube2472 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1211
Tmin = 0.947, Tmax = 0.967k = 99
7898 measured reflectionsl = 2423
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0849P)2 + 0.3832P]
where P = (Fo2 + 2Fc2)/3
2857 reflections(Δ/σ)max < 0.001
217 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.39 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
P10.05915 (5)0.18038 (8)0.17188 (3)0.0325 (2)
O10.25977 (17)0.1043 (3)0.26179 (8)0.0553 (5)
H1B0.31300.03180.27910.083*
C10.2131 (2)0.0652 (3)0.19367 (10)0.0382 (5)
H1A0.19520.05680.18900.046*
O20.03791 (17)0.0800 (2)0.20729 (9)0.0525 (5)
C20.3064 (2)0.1157 (3)0.14900 (10)0.0340 (5)
O30.00787 (15)0.1280 (2)0.09686 (7)0.0413 (4)
C30.4049 (2)0.2322 (3)0.16908 (13)0.0477 (6)
H3A0.41690.28030.21160.057*
O40.06661 (14)0.3619 (2)0.18491 (7)0.0375 (4)
C40.4865 (3)0.2785 (4)0.12638 (15)0.0565 (7)
H4A0.55360.35700.14050.068*
C50.4691 (3)0.2098 (4)0.06388 (15)0.0535 (7)
H5A0.52310.24300.03500.064*
C60.3727 (2)0.0924 (3)0.04379 (12)0.0477 (6)
H6A0.36140.04470.00120.057*
C70.2920 (2)0.0439 (3)0.08583 (11)0.0401 (6)
H7A0.22710.03770.07190.048*
C80.0956 (2)0.1331 (3)0.26030 (11)0.0373 (5)
C90.2250 (2)0.0869 (3)0.25534 (12)0.0483 (6)
H9A0.27120.03080.21750.058*
C100.2844 (3)0.1253 (4)0.30755 (15)0.0618 (8)
H10A0.37190.09420.30550.074*
C110.2164 (3)0.2085 (4)0.36221 (15)0.0649 (8)
H11A0.25740.23400.39750.078*
C120.0882 (3)0.2550 (4)0.36574 (13)0.0589 (8)
H12A0.04230.31330.40310.071*
C130.0268 (2)0.2158 (3)0.31414 (12)0.0461 (6)
H13A0.06090.24590.31640.055*
C140.0621 (2)0.2312 (3)0.04572 (11)0.0360 (5)
C150.1767 (2)0.3093 (3)0.05175 (13)0.0478 (6)
H15A0.20950.29780.09070.057*
C160.2426 (2)0.4055 (4)0.00118 (14)0.0552 (7)
H16A0.32110.45930.00190.066*
C170.1937 (3)0.4226 (4)0.05831 (13)0.0550 (7)
H17A0.23890.48760.09390.066*
C180.0790 (3)0.3444 (3)0.06281 (13)0.0534 (7)
H18A0.04570.35640.10160.064*
C190.0122 (2)0.2481 (3)0.01097 (12)0.0432 (6)
H19A0.06640.19470.01420.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0316 (3)0.0387 (4)0.0276 (3)0.0006 (2)0.0071 (2)0.0003 (2)
O10.0571 (11)0.0753 (14)0.0305 (9)0.0233 (9)0.0023 (8)0.0049 (8)
C10.0392 (13)0.0435 (14)0.0312 (11)0.0081 (10)0.0060 (10)0.0041 (10)
O20.0594 (11)0.0515 (11)0.0561 (11)0.0151 (9)0.0334 (9)0.0121 (9)
C20.0307 (11)0.0366 (13)0.0330 (11)0.0078 (9)0.0030 (9)0.0013 (9)
O30.0436 (9)0.0448 (10)0.0322 (9)0.0060 (7)0.0003 (7)0.0025 (7)
C30.0409 (14)0.0541 (16)0.0460 (14)0.0011 (11)0.0045 (11)0.0137 (12)
O40.0372 (9)0.0386 (9)0.0360 (8)0.0006 (7)0.0061 (7)0.0004 (7)
C40.0392 (14)0.0540 (17)0.078 (2)0.0114 (12)0.0155 (14)0.0174 (15)
C50.0466 (15)0.0566 (17)0.0648 (18)0.0011 (12)0.0285 (14)0.0010 (14)
C60.0443 (14)0.0603 (17)0.0412 (13)0.0038 (12)0.0155 (11)0.0044 (12)
C70.0358 (12)0.0447 (14)0.0390 (12)0.0023 (10)0.0059 (10)0.0070 (11)
C80.0391 (12)0.0408 (13)0.0351 (12)0.0014 (10)0.0148 (10)0.0051 (10)
C90.0405 (14)0.0583 (17)0.0452 (14)0.0099 (12)0.0074 (11)0.0017 (12)
C100.0423 (15)0.080 (2)0.072 (2)0.0064 (14)0.0313 (14)0.0031 (16)
C110.074 (2)0.078 (2)0.0537 (18)0.0067 (16)0.0386 (16)0.0052 (15)
C120.0691 (19)0.074 (2)0.0360 (14)0.0148 (15)0.0161 (13)0.0067 (13)
C130.0386 (13)0.0585 (16)0.0419 (14)0.0081 (11)0.0101 (11)0.0020 (12)
C140.0325 (12)0.0387 (13)0.0337 (12)0.0061 (9)0.0001 (10)0.0018 (10)
C150.0371 (13)0.0615 (17)0.0456 (14)0.0002 (11)0.0103 (11)0.0050 (12)
C160.0378 (14)0.0590 (18)0.0648 (17)0.0045 (12)0.0013 (13)0.0055 (14)
C170.0568 (17)0.0534 (17)0.0472 (15)0.0075 (13)0.0067 (13)0.0112 (13)
C180.0630 (18)0.0578 (17)0.0379 (14)0.0148 (14)0.0071 (13)0.0022 (12)
C190.0395 (13)0.0533 (16)0.0372 (13)0.0068 (11)0.0092 (11)0.0047 (11)
Geometric parameters (Å, º) top
P1—O41.4541 (17)C8—C91.371 (3)
P1—O31.5640 (16)C9—C101.369 (3)
P1—O21.5677 (16)C9—H9A0.9300
P1—C11.806 (2)C10—C111.355 (4)
O1—C11.404 (3)C10—H10A0.9300
O1—H1B0.8200C11—C121.364 (4)
C1—C21.512 (3)C11—H11A0.9300
C1—H1A0.9800C12—C131.372 (4)
O2—C81.402 (3)C12—H12A0.9300
C2—C31.369 (3)C13—H13A0.9300
C2—C71.384 (3)C14—C151.364 (3)
O3—C141.398 (3)C14—C191.366 (3)
C3—C41.382 (4)C15—C161.376 (4)
C3—H3A0.9300C15—H15A0.9300
C4—C51.360 (4)C16—C171.369 (4)
C4—H4A0.9300C16—H16A0.9300
C5—C61.360 (4)C17—C181.357 (4)
C5—H5A0.9300C17—H17A0.9300
C6—C71.369 (3)C18—C191.365 (4)
C6—H6A0.9300C18—H18A0.9300
C7—H7A0.9300C19—H19A0.9300
C8—C131.344 (3)
O4—P1—O3115.60 (9)C9—C8—O2115.5 (2)
O4—P1—O2115.29 (9)C10—C9—C8118.3 (2)
O3—P1—O2101.35 (9)C10—C9—H9A120.8
O4—P1—C1116.05 (11)C8—C9—H9A120.8
O3—P1—C1102.06 (9)C11—C10—C9120.3 (3)
O2—P1—C1104.50 (11)C11—C10—H10A119.9
C1—O1—H1B109.5C9—C10—H10A119.9
O1—C1—C2113.91 (19)C10—C11—C12120.4 (3)
O1—C1—P1103.66 (15)C10—C11—H11A119.8
C2—C1—P1111.20 (15)C12—C11—H11A119.8
O1—C1—H1A109.3C11—C12—C13120.0 (3)
C2—C1—H1A109.3C11—C12—H12A120.0
P1—C1—H1A109.3C13—C12—H12A120.0
C8—O2—P1128.34 (15)C8—C13—C12118.9 (2)
C3—C2—C7118.7 (2)C8—C13—H13A120.6
C3—C2—C1121.7 (2)C12—C13—H13A120.6
C7—C2—C1119.5 (2)C15—C14—C19121.5 (2)
C14—O3—P1126.23 (15)C15—C14—O3121.3 (2)
C2—C3—C4120.3 (2)C19—C14—O3117.2 (2)
C2—C3—H3A119.9C14—C15—C16118.4 (2)
C4—C3—H3A119.9C14—C15—H15A120.8
C5—C4—C3120.3 (2)C16—C15—H15A120.8
C5—C4—H4A119.8C17—C16—C15120.6 (3)
C3—C4—H4A119.8C17—C16—H16A119.7
C6—C5—C4119.8 (2)C15—C16—H16A119.7
C6—C5—H5A120.1C18—C17—C16119.8 (3)
C4—C5—H5A120.1C18—C17—H17A120.1
C5—C6—C7120.5 (2)C16—C17—H17A120.1
C5—C6—H6A119.8C17—C18—C19120.6 (2)
C7—C6—H6A119.8C17—C18—H18A119.7
C6—C7—C2120.3 (2)C19—C18—H18A119.7
C6—C7—H7A119.8C18—C19—C14119.1 (2)
C2—C7—H7A119.8C18—C19—H19A120.4
C13—C8—C9122.1 (2)C14—C19—H19A120.4
C13—C8—O2122.3 (2)
O4—P1—C1—O155.55 (18)C3—C2—C7—C61.7 (4)
O3—P1—C1—O1177.85 (15)C1—C2—C7—C6177.7 (2)
O2—P1—C1—O172.59 (17)P1—O2—C8—C1343.4 (3)
O4—P1—C1—C267.24 (18)P1—O2—C8—C9140.1 (2)
O3—P1—C1—C259.36 (18)C13—C8—C9—C100.7 (4)
O2—P1—C1—C2164.62 (15)O2—C8—C9—C10175.8 (2)
O4—P1—O2—C815.2 (2)C8—C9—C10—C110.6 (5)
O3—P1—O2—C8140.8 (2)C9—C10—C11—C120.1 (5)
C1—P1—O2—C8113.4 (2)C10—C11—C12—C130.8 (5)
O1—C1—C2—C318.8 (3)C9—C8—C13—C120.0 (4)
P1—C1—C2—C397.9 (2)O2—C8—C13—C12176.3 (2)
O1—C1—C2—C7161.8 (2)C11—C12—C13—C80.7 (5)
P1—C1—C2—C781.5 (2)P1—O3—C14—C1555.5 (3)
O4—P1—O3—C1417.9 (2)P1—O3—C14—C19125.6 (2)
O2—P1—O3—C14107.50 (18)C19—C14—C15—C160.6 (4)
C1—P1—O3—C14144.80 (17)O3—C14—C15—C16178.3 (2)
C7—C2—C3—C41.0 (4)C14—C15—C16—C170.3 (4)
C1—C2—C3—C4178.4 (2)C15—C16—C17—C180.1 (4)
C2—C3—C4—C50.5 (4)C16—C17—C18—C190.3 (4)
C3—C4—C5—C61.3 (4)C17—C18—C19—C140.0 (4)
C4—C5—C6—C70.6 (4)C15—C14—C19—C180.5 (4)
C5—C6—C7—C21.0 (4)O3—C14—C19—C18178.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1B···O4i0.821.872.691 (2)178
Symmetry code: (i) x+1/2, y1/2, z+1/2.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds