In the title compound, C
18H
20ClO
4P, the P atom is in a distorted tetrahedral configuration. In the crystal structure, molecules are linked by intermolecular C—H
O and O—H
O hydrogen bonds.
Supporting information
CCDC reference: 628427
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.006 Å
- R factor = 0.054
- wR factor = 0.112
- Data-to-parameter ratio = 17.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.08 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.08 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for C8 - C11 .. 5.95 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT731_ALERT_1_C Bond Calc 0.81(3), Rep 0.814(10) ...... 3.00 su-Ra
O4 -H4A 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.81(3), Rep 0.814(10) ...... 3.00 su-Ra
O4 -H4A 1.555 1.555
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 26.99
From the CIF: _reflns_number_total 3837
Count of symmetry unique reflns 2148
Completeness (_total/calc) 178.63%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1689
Fraction of Friedel pairs measured 0.786
Are heavy atom types Z>Si present yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of P1 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12 = . R
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
4 ALERT level G = General alerts; check
5 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
2 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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.
2-[(4-Chlorophenyl)hydroxymethyl]-5,5-dimethyl-4-phenyl-1,3,2-
dioxaphosphorinan-2-one
top
Crystal data top
C18H20ClO4P | F(000) = 384 |
Mr = 366.76 | Dx = 1.353 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.5609 (14) Å | Cell parameters from 1701 reflections |
b = 6.4450 (9) Å | θ = 3.0–19.2° |
c = 14.1161 (19) Å | µ = 0.32 mm−1 |
β = 110.475 (2)° | T = 292 K |
V = 900.1 (2) Å3 | Needle, colorless |
Z = 2 | 0.30 × 0.10 × 0.05 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2940 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 27.0°, θmin = 1.5° |
φ and ω scans | h = −13→13 |
6763 measured reflections | k = −8→8 |
3837 independent reflections | l = −18→15 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.112 | w = 1/[σ2(Fo2) + (0.0477P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
3837 reflections | Δρmax = 0.30 e Å−3 |
222 parameters | Δρmin = −0.23 e Å−3 |
2 restraints | Absolute structure: Flack (1983), 1711 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.11 (9) |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.7869 (4) | 0.4345 (7) | 0.3121 (3) | 0.0733 (12) | |
H1 | 0.7661 | 0.3308 | 0.2632 | 0.088* | |
C2 | 0.7837 (5) | 0.3911 (11) | 0.4070 (5) | 0.111 (2) | |
H2 | 0.7619 | 0.2585 | 0.4223 | 0.133* | |
C3 | 0.8128 (6) | 0.5450 (14) | 0.4785 (4) | 0.123 (3) | |
H3 | 0.8111 | 0.5164 | 0.5426 | 0.148* | |
C4 | 0.8446 (5) | 0.7423 (12) | 0.4556 (4) | 0.110 (2) | |
H4 | 0.8626 | 0.8468 | 0.5040 | 0.132* | |
C5 | 0.8497 (4) | 0.7845 (8) | 0.3611 (3) | 0.0722 (12) | |
H5 | 0.8727 | 0.9166 | 0.3461 | 0.087* | |
C6 | 0.8206 (3) | 0.6293 (6) | 0.2890 (3) | 0.0522 (9) | |
C7 | 0.8224 (3) | 0.6693 (5) | 0.1847 (2) | 0.0422 (8) | |
H7 | 0.7634 | 0.5668 | 0.1390 | 0.051* | |
C8 | 0.9611 (3) | 0.6594 (5) | 0.1718 (2) | 0.0421 (8) | |
C9 | 1.0204 (3) | 0.4411 (6) | 0.1976 (3) | 0.0562 (9) | |
H9A | 0.9561 | 0.3408 | 0.1586 | 0.084* | |
H9B | 1.0407 | 0.4148 | 0.2683 | 0.084* | |
H9C | 1.1018 | 0.4309 | 0.1821 | 0.084* | |
C10 | 1.0617 (3) | 0.8184 (6) | 0.2361 (3) | 0.0616 (11) | |
H10A | 1.1420 | 0.8163 | 0.2189 | 0.092* | |
H10B | 1.0844 | 0.7848 | 0.3063 | 0.092* | |
H10C | 1.0219 | 0.9542 | 0.2234 | 0.092* | |
C11 | 0.9365 (3) | 0.6936 (5) | 0.0603 (3) | 0.0510 (9) | |
H11A | 1.0221 | 0.6851 | 0.0493 | 0.061* | |
H11B | 0.8787 | 0.5837 | 0.0214 | 0.061* | |
C12 | 0.6008 (3) | 0.8405 (5) | −0.0450 (2) | 0.0401 (7) | |
H12 | 0.6069 | 0.6901 | −0.0339 | 0.048* | |
C13 | 0.5934 (3) | 0.8872 (5) | −0.1514 (2) | 0.0413 (7) | |
C14 | 0.6288 (3) | 0.7374 (6) | −0.2082 (3) | 0.0521 (9) | |
H14 | 0.6537 | 0.6056 | −0.1813 | 0.062* | |
C15 | 0.6274 (4) | 0.7821 (7) | −0.3047 (3) | 0.0617 (10) | |
H15 | 0.6503 | 0.6806 | −0.3427 | 0.074* | |
C16 | 0.5921 (3) | 0.9767 (8) | −0.3434 (3) | 0.0604 (9) | |
C17 | 0.5519 (4) | 1.1255 (6) | −0.2902 (3) | 0.0602 (10) | |
H17 | 0.5242 | 1.2554 | −0.3185 | 0.072* | |
C18 | 0.5530 (3) | 1.0800 (6) | −0.1943 (2) | 0.0517 (8) | |
H18 | 0.5263 | 1.1807 | −0.1580 | 0.062* | |
Cl1 | 0.59736 (12) | 1.0368 (2) | −0.46172 (8) | 0.0987 (5) | |
O1 | 0.8739 (2) | 0.8931 (4) | 0.02358 (17) | 0.0492 (6) | |
O2 | 0.7628 (2) | 0.8759 (3) | 0.15361 (15) | 0.0449 (6) | |
O3 | 0.7338 (2) | 1.1924 (3) | 0.04441 (18) | 0.0519 (6) | |
O4 | 0.4888 (2) | 0.9201 (3) | −0.02239 (18) | 0.0487 (6) | |
H4A | 0.434 (3) | 0.830 (4) | −0.025 (3) | 0.073* | |
P1 | 0.74643 (7) | 0.96582 (13) | 0.04676 (6) | 0.0385 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.072 (2) | 0.079 (3) | 0.073 (3) | 0.018 (2) | 0.032 (2) | 0.032 (3) |
C2 | 0.111 (4) | 0.131 (5) | 0.115 (5) | 0.047 (4) | 0.070 (4) | 0.075 (4) |
C3 | 0.123 (4) | 0.197 (8) | 0.068 (3) | 0.082 (5) | 0.057 (3) | 0.077 (5) |
C4 | 0.112 (4) | 0.171 (7) | 0.049 (3) | 0.061 (4) | 0.028 (3) | 0.012 (4) |
C5 | 0.077 (3) | 0.096 (4) | 0.045 (2) | 0.019 (2) | 0.023 (2) | 0.007 (2) |
C6 | 0.0424 (17) | 0.071 (3) | 0.042 (2) | 0.0105 (16) | 0.0134 (15) | 0.0118 (19) |
C7 | 0.0416 (16) | 0.0381 (19) | 0.0415 (19) | 0.0044 (14) | 0.0080 (14) | 0.0010 (15) |
C8 | 0.0376 (15) | 0.0425 (19) | 0.0433 (19) | 0.0025 (14) | 0.0104 (14) | −0.0033 (15) |
C9 | 0.0504 (17) | 0.051 (2) | 0.060 (2) | 0.0121 (17) | 0.0094 (16) | 0.0016 (19) |
C10 | 0.0456 (19) | 0.063 (3) | 0.066 (3) | −0.0042 (18) | 0.0073 (17) | −0.008 (2) |
C11 | 0.0450 (18) | 0.049 (2) | 0.062 (2) | 0.0096 (16) | 0.0231 (17) | −0.0023 (18) |
C12 | 0.0400 (16) | 0.0343 (19) | 0.047 (2) | −0.0022 (13) | 0.0172 (14) | 0.0013 (15) |
C13 | 0.0355 (15) | 0.0434 (18) | 0.0412 (18) | −0.0047 (14) | 0.0088 (13) | 0.0032 (15) |
C14 | 0.0528 (19) | 0.051 (2) | 0.047 (2) | −0.0028 (17) | 0.0110 (16) | −0.0054 (18) |
C15 | 0.061 (2) | 0.073 (3) | 0.049 (2) | −0.003 (2) | 0.0181 (19) | −0.014 (2) |
C16 | 0.0515 (18) | 0.082 (3) | 0.0444 (19) | −0.012 (2) | 0.0123 (15) | 0.004 (2) |
C17 | 0.066 (2) | 0.056 (3) | 0.054 (2) | −0.0008 (18) | 0.0147 (19) | 0.0109 (19) |
C18 | 0.0526 (19) | 0.054 (2) | 0.048 (2) | −0.0023 (18) | 0.0164 (16) | −0.001 (2) |
Cl1 | 0.1131 (9) | 0.1350 (14) | 0.0539 (6) | −0.0044 (8) | 0.0368 (6) | 0.0135 (7) |
O1 | 0.0446 (11) | 0.0513 (15) | 0.0560 (14) | 0.0055 (10) | 0.0230 (10) | 0.0078 (11) |
O2 | 0.0434 (11) | 0.0500 (14) | 0.0413 (13) | 0.0118 (10) | 0.0150 (10) | 0.0024 (11) |
O3 | 0.0420 (12) | 0.0423 (15) | 0.0633 (16) | −0.0003 (11) | 0.0082 (11) | −0.0006 (12) |
O4 | 0.0394 (11) | 0.0426 (16) | 0.0684 (15) | −0.0065 (9) | 0.0243 (11) | −0.0082 (12) |
P1 | 0.0355 (4) | 0.0362 (4) | 0.0427 (4) | 0.0025 (4) | 0.0121 (3) | 0.0016 (4) |
Geometric parameters (Å, º) top
C1—C6 | 1.375 (6) | C10—H10C | 0.9600 |
C1—C2 | 1.380 (6) | C11—O1 | 1.456 (4) |
C1—H1 | 0.9300 | C11—H11A | 0.9700 |
C2—C3 | 1.371 (9) | C11—H11B | 0.9700 |
C2—H2 | 0.9300 | C12—O4 | 1.425 (3) |
C3—C4 | 1.382 (10) | C12—C13 | 1.507 (4) |
C3—H3 | 0.9300 | C12—P1 | 1.817 (3) |
C4—C5 | 1.380 (6) | C12—H12 | 0.9800 |
C4—H4 | 0.9300 | C13—C18 | 1.383 (5) |
C5—C6 | 1.383 (5) | C13—C14 | 1.387 (5) |
C5—H5 | 0.9300 | C14—C15 | 1.388 (5) |
C6—C7 | 1.502 (4) | C14—H14 | 0.9300 |
C7—O2 | 1.472 (4) | C15—C16 | 1.366 (6) |
C7—C8 | 1.539 (4) | C15—H15 | 0.9300 |
C7—H7 | 0.9800 | C16—C17 | 1.374 (5) |
C8—C11 | 1.519 (4) | C16—Cl1 | 1.735 (3) |
C8—C10 | 1.526 (5) | C17—C18 | 1.380 (5) |
C8—C9 | 1.532 (5) | C17—H17 | 0.9300 |
C9—H9A | 0.9600 | C18—H18 | 0.9300 |
C9—H9B | 0.9600 | O1—P1 | 1.564 (2) |
C9—H9C | 0.9600 | O2—P1 | 1.568 (2) |
C10—H10A | 0.9600 | O3—P1 | 1.466 (2) |
C10—H10B | 0.9600 | O4—H4A | 0.814 (10) |
| | | |
C6—C1—C2 | 120.7 (5) | H10B—C10—H10C | 109.5 |
C6—C1—H1 | 119.6 | O1—C11—C8 | 112.9 (3) |
C2—C1—H1 | 119.6 | O1—C11—H11A | 109.0 |
C3—C2—C1 | 119.5 (5) | C8—C11—H11A | 109.0 |
C3—C2—H2 | 120.2 | O1—C11—H11B | 109.0 |
C1—C2—H2 | 120.2 | C8—C11—H11B | 109.0 |
C2—C3—C4 | 120.3 (5) | H11A—C11—H11B | 107.8 |
C2—C3—H3 | 119.9 | O4—C12—C13 | 113.2 (2) |
C4—C3—H3 | 119.9 | O4—C12—P1 | 104.02 (19) |
C5—C4—C3 | 120.1 (6) | C13—C12—P1 | 111.0 (2) |
C5—C4—H4 | 119.9 | O4—C12—H12 | 109.5 |
C3—C4—H4 | 119.9 | C13—C12—H12 | 109.5 |
C4—C5—C6 | 119.7 (5) | P1—C12—H12 | 109.5 |
C4—C5—H5 | 120.2 | C18—C13—C14 | 118.4 (3) |
C6—C5—H5 | 120.2 | C18—C13—C12 | 121.1 (3) |
C1—C6—C5 | 119.7 (4) | C14—C13—C12 | 120.4 (3) |
C1—C6—C7 | 118.9 (4) | C13—C14—C15 | 120.7 (4) |
C5—C6—C7 | 121.5 (3) | C13—C14—H14 | 119.7 |
O2—C7—C6 | 107.3 (2) | C15—C14—H14 | 119.7 |
O2—C7—C8 | 109.1 (2) | C16—C15—C14 | 119.4 (4) |
C6—C7—C8 | 116.6 (2) | C16—C15—H15 | 120.3 |
O2—C7—H7 | 107.8 | C14—C15—H15 | 120.3 |
C6—C7—H7 | 107.8 | C15—C16—C17 | 121.0 (3) |
C8—C7—H7 | 107.8 | C15—C16—Cl1 | 119.6 (3) |
C11—C8—C10 | 110.5 (3) | C17—C16—Cl1 | 119.4 (4) |
C11—C8—C9 | 106.7 (3) | C16—C17—C18 | 119.3 (4) |
C10—C8—C9 | 109.5 (3) | C16—C17—H17 | 120.4 |
C11—C8—C7 | 107.0 (2) | C18—C17—H17 | 120.4 |
C10—C8—C7 | 113.3 (3) | C17—C18—C13 | 121.1 (4) |
C9—C8—C7 | 109.7 (3) | C17—C18—H18 | 119.5 |
C8—C9—H9A | 109.5 | C13—C18—H18 | 119.5 |
C8—C9—H9B | 109.5 | C11—O1—P1 | 120.48 (19) |
H9A—C9—H9B | 109.5 | C7—O2—P1 | 120.84 (18) |
C8—C9—H9C | 109.5 | C12—O4—H4A | 112 (3) |
H9A—C9—H9C | 109.5 | O3—P1—O1 | 111.83 (13) |
H9B—C9—H9C | 109.5 | O3—P1—O2 | 111.64 (13) |
C8—C10—H10A | 109.5 | O1—P1—O2 | 106.09 (11) |
C8—C10—H10B | 109.5 | O3—P1—C12 | 112.29 (14) |
H10A—C10—H10B | 109.5 | O1—P1—C12 | 107.05 (13) |
C8—C10—H10C | 109.5 | O2—P1—C12 | 107.60 (13) |
H10A—C10—H10C | 109.5 | | |
| | | |
C6—C1—C2—C3 | 0.8 (7) | C18—C13—C14—C15 | 1.8 (5) |
C1—C2—C3—C4 | 0.3 (8) | C12—C13—C14—C15 | −177.3 (3) |
C2—C3—C4—C5 | −1.2 (8) | C13—C14—C15—C16 | 0.7 (5) |
C3—C4—C5—C6 | 1.1 (7) | C14—C15—C16—C17 | −3.1 (5) |
C2—C1—C6—C5 | −0.9 (6) | C14—C15—C16—Cl1 | 177.2 (3) |
C2—C1—C6—C7 | −179.9 (3) | C15—C16—C17—C18 | 2.9 (5) |
C4—C5—C6—C1 | −0.1 (6) | Cl1—C16—C17—C18 | −177.4 (2) |
C4—C5—C6—C7 | 178.9 (3) | C16—C17—C18—C13 | −0.3 (5) |
C1—C6—C7—O2 | 139.3 (3) | C14—C13—C18—C17 | −2.0 (5) |
C5—C6—C7—O2 | −39.6 (4) | C12—C13—C18—C17 | 177.1 (3) |
C1—C6—C7—C8 | −98.0 (4) | C8—C11—O1—P1 | −48.8 (3) |
C5—C6—C7—C8 | 83.0 (4) | C6—C7—O2—P1 | −178.86 (19) |
O2—C7—C8—C11 | −61.2 (3) | C8—C7—O2—P1 | 54.0 (3) |
C6—C7—C8—C11 | 177.1 (3) | C11—O1—P1—O3 | 155.1 (2) |
O2—C7—C8—C10 | 60.8 (3) | C11—O1—P1—O2 | 33.2 (3) |
C6—C7—C8—C10 | −60.9 (4) | C11—O1—P1—C12 | −81.5 (3) |
O2—C7—C8—C9 | −176.5 (2) | C7—O2—P1—O3 | −158.9 (2) |
C6—C7—C8—C9 | 61.8 (4) | C7—O2—P1—O1 | −36.8 (2) |
C10—C8—C11—O1 | −63.7 (3) | C7—O2—P1—C12 | 77.5 (2) |
C9—C8—C11—O1 | 177.4 (2) | O4—C12—P1—O3 | −54.5 (2) |
C7—C8—C11—O1 | 60.0 (3) | C13—C12—P1—O3 | 67.5 (3) |
O4—C12—C13—C18 | 42.4 (4) | O4—C12—P1—O1 | −177.56 (18) |
P1—C12—C13—C18 | −74.1 (3) | C13—C12—P1—O1 | −55.6 (2) |
O4—C12—C13—C14 | −138.5 (3) | O4—C12—P1—O2 | 68.8 (2) |
P1—C12—C13—C14 | 105.0 (3) | C13—C12—P1—O2 | −169.2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11A···O1i | 0.97 | 2.57 | 3.290 (4) | 131 |
C12—H12···O4ii | 0.98 | 2.29 | 3.126 (4) | 143 |
C9—H9A···O3iii | 0.96 | 2.52 | 3.439 (4) | 159 |
O4—H4A···O3ii | 0.81 (1) | 1.91 (2) | 2.696 (3) | 161 (4) |
Symmetry codes: (i) −x+2, y−1/2, −z; (ii) −x+1, y−1/2, −z; (iii) x, y−1, z. |