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The title compound, C16H20NO2P [O=P(C6H5)(C6H4OH)(Et2N) or P(Ph)(PhOH)(Et2N)], crystallizes as a 21:79 racemic mixture of the R and S isomers in the asymmetric unit and is stabilized by strong intramolecular hydrogen bonds with H...O = 1.97 (4) and 1.84 (5) Å. The Tolman cone angle is calculated to be 199°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804014850/hg6060sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804014850/hg6060Isup2.hkl
Contains datablock I

CCDC reference: 245329

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.057
  • wR factor = 0.145
  • Data-to-parameter ratio = 19.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.77 Ratio PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C15 PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT415_ALERT_2_C Short Inter D-H..H-X H10 .. H2B .. 2.12 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H8A .. O1 .. 2.61 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART-NT (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus and XPREP (Bruker, 1999); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top
Crystal data top
C16H20NO2PF(000) = 616
Mr = 289.3Dx = 1.232 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybcCell parameters from 789 reflections
a = 8.4348 (15) Åθ = 2.9–22.9°
b = 13.635 (2) ŵ = 0.18 mm1
c = 13.842 (2) ÅT = 294 K
β = 101.606 (3)°Plates, colorless
V = 1559.4 (5) Å30.44 × 0.15 × 0.08 mm
Z = 4
Data collection top
Bruker SMART 1K CCD
diffractometer
Rint = 0.060
ω scansθmax = 28.3°, θmin = 2.1°
10440 measured reflectionsh = 911
3854 independent reflectionsk = 1816
2053 reflections with I > 2σ(I)l = 1817
Refinement top
Refinement on F24 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.057 w = 1/[σ2(Fo2) + (0.0595P)2 + 0.1233P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.145(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.27 e Å3
3854 reflectionsΔρmin = 0.29 e Å3
199 parameters
Special details top

Experimental. The intensity data was collected on a Siemens SMART CCD 1 K diffractometer using an exposure time of 30 s/frame. A total of 1350 frames were collected with a frame width of 0.3° covering up to θ = 28.33° with 98.9% completeness accomplished. The first 50 frames were recollected at the end of each data collection to check for decay; none was found.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
P0.33957 (8)0.47060 (5)0.23808 (5)0.0386 (2)
O10.2463 (2)0.44905 (13)0.31624 (12)0.0522 (5)
N0.3091 (2)0.57609 (14)0.17943 (13)0.0431 (5)
C130.1536 (3)0.5914 (2)0.1095 (2)0.0591 (8)
H13A0.08390.63220.14060.071*
H13B0.10040.52860.09440.071*
C140.1756 (5)0.6394 (3)0.0147 (2)0.0920 (11)
H14A0.23140.70060.02940.138*
H14B0.07160.6510.02670.138*
H14C0.23780.5970.01880.138*
C150.3802 (3)0.66596 (19)0.2303 (2)0.0557 (7)
H15A0.37920.7170.18130.067*
H15B0.49250.65270.25990.067*
C160.2977 (5)0.7045 (3)0.3088 (3)0.1025 (13)
H16A0.1840.71190.28230.154*
H16B0.34310.7670.33130.154*
H16C0.3130.65930.36310.154*
C10.5534 (3)0.46614 (16)0.28914 (17)0.0370 (5)
C30.7691 (4)0.4318 (2)0.4279 (2)0.0720 (9)
H30.80270.41550.49410.086*
C40.8805 (4)0.4466 (2)0.3714 (3)0.0693 (9)
H40.99020.44020.39870.083*
C50.8321 (4)0.4709 (3)0.2742 (3)0.0725 (9)
H50.90880.48010.23540.087*
C60.6705 (3)0.4819 (2)0.2336 (2)0.0584 (8)
H60.63920.50010.16770.07*
C70.2973 (3)0.37750 (17)0.14421 (17)0.0403 (6)
C90.2049 (4)0.2134 (2)0.0949 (2)0.0708 (9)
H90.15710.15490.10840.085*
C100.2555 (4)0.2245 (3)0.0087 (3)0.0793 (10)
H100.24290.17310.03640.095*
C110.3251 (4)0.3106 (3)0.0130 (2)0.0768 (10)
H110.35760.3180.07290.092*
C120.3463 (3)0.3856 (2)0.0545 (2)0.0603 (8)
H120.39490.44350.03980.072*
O20.5261 (11)0.4095 (10)0.4487 (6)0.091 (5)0.213 (6)
C20.6049 (4)0.4408 (2)0.3877 (2)0.0553 (7)
H2A0.52920.42980.4270.066*0.787 (6)
C80.2242 (3)0.2899 (2)0.16384 (19)0.0522 (7)
H8A0.18830.28230.22270.063*0.213 (6)
O80.1689 (4)0.2719 (2)0.2458 (2)0.0788 (11)0.787 (6)
H2B0.427 (3)0.415 (13)0.424 (7)0.118*0.213 (6)
H8B0.173 (6)0.326 (4)0.277 (4)0.118*0.787 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P0.0364 (4)0.0379 (4)0.0414 (4)0.0006 (3)0.0074 (3)0.0001 (3)
O10.0476 (11)0.0569 (12)0.0562 (10)0.0030 (8)0.0202 (9)0.0003 (9)
N0.0423 (12)0.0357 (12)0.0467 (11)0.0005 (9)0.0018 (10)0.0011 (10)
C130.0474 (17)0.0524 (18)0.0691 (18)0.0046 (13)0.0083 (14)0.0081 (15)
C140.098 (3)0.097 (3)0.068 (2)0.010 (2)0.0127 (19)0.027 (2)
C150.0586 (18)0.0367 (15)0.0660 (17)0.0032 (13)0.0016 (15)0.0033 (14)
C160.151 (4)0.065 (2)0.103 (3)0.016 (2)0.053 (3)0.031 (2)
C10.0375 (13)0.0306 (12)0.0415 (13)0.0003 (11)0.0043 (11)0.0027 (11)
C30.073 (2)0.065 (2)0.0643 (19)0.0067 (17)0.0189 (18)0.0163 (16)
C40.0444 (18)0.060 (2)0.094 (3)0.0096 (14)0.0091 (18)0.0106 (18)
C50.0453 (18)0.091 (3)0.084 (2)0.0014 (17)0.0198 (18)0.022 (2)
C60.0433 (17)0.082 (2)0.0503 (15)0.0015 (15)0.0114 (14)0.0036 (15)
C70.0391 (14)0.0369 (14)0.0424 (13)0.0021 (11)0.0020 (11)0.0014 (11)
C90.078 (2)0.0389 (18)0.085 (2)0.0062 (15)0.0093 (19)0.0044 (17)
C100.090 (3)0.062 (2)0.078 (2)0.0061 (19)0.003 (2)0.0277 (19)
C110.094 (3)0.077 (2)0.0624 (19)0.009 (2)0.0210 (18)0.0255 (18)
C120.068 (2)0.0550 (18)0.0583 (17)0.0096 (15)0.0145 (15)0.0091 (15)
O20.059 (7)0.166 (12)0.043 (6)0.045 (7)0.001 (5)0.027 (6)
C20.0523 (18)0.0591 (18)0.0509 (16)0.0069 (14)0.0020 (15)0.0026 (14)
C80.0545 (17)0.0470 (18)0.0507 (16)0.0026 (13)0.0001 (14)0.0058 (14)
O80.106 (2)0.0608 (19)0.072 (2)0.0267 (17)0.0213 (17)0.0048 (14)
Geometric parameters (Å, º) top
P—O11.4896 (17)C3—C21.391 (4)
P—N1.646 (2)C3—H30.93
P—C71.800 (2)C4—C51.365 (4)
P—C11.801 (2)C4—H40.93
N—C151.479 (3)C5—C61.374 (4)
N—C131.480 (3)C5—H50.93
C13—C141.511 (4)C6—H60.93
C13—H13A0.97C7—C121.390 (3)
C13—H13B0.97C7—C81.396 (3)
C14—H14A0.96C9—C101.355 (4)
C14—H14B0.96C9—C81.400 (4)
C14—H14C0.96C9—H90.93
C15—C161.499 (4)C10—C111.372 (5)
C15—H15A0.97C10—H100.93
C15—H15B0.97C11—C121.373 (4)
C16—H16A0.96C11—H110.93
C16—H16B0.96C12—H120.93
C16—H16C0.96O2—H2B0.84 (2)
C1—C61.385 (3)C2—H2A0.93
C1—C21.390 (4)C8—H8A0.93
C3—C41.353 (4)O8—H8B0.85 (5)
O1—P—N118.53 (10)C2—C1—P119.0 (2)
O1—P—C7109.16 (11)C4—C3—C2120.5 (3)
N—P—C7105.75 (10)C4—C3—H3119.7
O1—P—C1110.00 (10)C2—C3—H3119.7
N—P—C1105.53 (10)C3—C4—C5120.0 (3)
C7—P—C1107.27 (11)C3—C4—H4120
C15—N—C13114.6 (2)C5—C4—H4120
C15—N—P118.76 (16)C4—C5—C6120.4 (3)
C13—N—P118.38 (16)C4—C5—H5119.8
N—C13—C14112.4 (2)C6—C5—H5119.8
N—C13—H13A109.1C5—C6—C1121.0 (3)
C14—C13—H13A109.1C5—C6—H6119.5
N—C13—H13B109.1C1—C6—H6119.5
C14—C13—H13B109.1C12—C7—C8117.7 (2)
H13A—C13—H13B107.9C12—C7—P122.49 (19)
C13—C14—H14A109.5C8—C7—P119.61 (19)
C13—C14—H14B109.5C10—C9—C8120.2 (3)
H14A—C14—H14B109.5C10—C9—H9119.9
C13—C14—H14C109.5C8—C9—H9119.9
H14A—C14—H14C109.5C9—C10—C11120.9 (3)
H14B—C14—H14C109.5C9—C10—H10119.6
N—C15—C16115.6 (2)C11—C10—H10119.6
N—C15—H15A108.4C10—C11—C12119.4 (3)
C16—C15—H15A108.4C10—C11—H11120.3
N—C15—H15B108.4C12—C11—H11120.3
C16—C15—H15B108.4C11—C12—C7121.8 (3)
H15A—C15—H15B107.4C11—C12—H12119.1
C15—C16—H16A109.5C7—C12—H12119.1
C15—C16—H16B109.5C1—C2—C3120.2 (3)
H16A—C16—H16B109.5C1—C2—H2A119.9
C15—C16—H16C109.5C3—C2—H2A119.9
H16A—C16—H16C109.5C7—C8—C9120.0 (3)
H16B—C16—H16C109.5C7—C8—H8A120
C6—C1—C2117.8 (2)C9—C8—H8A120
C6—C1—P123.12 (19)
O1—P—N—C1575.8 (2)P—C1—C6—C5175.4 (2)
C7—P—N—C15161.42 (19)O1—P—C7—C12169.7 (2)
C1—P—N—C1547.9 (2)N—P—C7—C1241.2 (2)
O1—P—N—C1370.9 (2)C1—P—C7—C1271.1 (2)
C7—P—N—C1351.9 (2)O1—P—C7—C815.6 (2)
C1—P—N—C13165.38 (18)N—P—C7—C8144.2 (2)
C15—N—C13—C1475.3 (3)C1—P—C7—C8103.6 (2)
P—N—C13—C14136.6 (2)C8—C9—C10—C110.5 (5)
C13—N—C15—C1673.3 (3)C9—C10—C11—C121.2 (5)
P—N—C15—C1674.6 (3)C10—C11—C12—C70.8 (5)
O1—P—C1—C6179.1 (2)C8—C7—C12—C110.3 (4)
N—P—C1—C651.9 (2)P—C7—C12—C11174.5 (2)
C7—P—C1—C660.5 (2)C6—C1—C2—C30.0 (4)
O1—P—C1—C22.6 (2)P—C1—C2—C3176.7 (2)
N—P—C1—C2131.5 (2)C4—C3—C2—C10.7 (4)
C7—P—C1—C2116.0 (2)C12—C7—C8—C91.0 (4)
C2—C3—C4—C50.3 (5)P—C7—C8—C9173.9 (2)
C3—C4—C5—C60.9 (5)C10—C9—C8—C70.7 (4)
C4—C5—C6—C11.7 (5)C14—C13—C15—C16128.2 (3)
C2—C1—C6—C51.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2B···O10.84 (2)1.97 (4)2.735 (9)152 (7)
O8—H8B···O10.85 (5)1.84 (5)2.637 (3)157 (5)
C2—H2A···O10.932.582.989 (3)107
C8—H8A···O10.932.613.006 (3)106
Comparative geometrical data (Å, °) for OP(Ph)(X)(N(Y)(Z)) compounds top
(X)(Y)(Z)OPN—POP—NC—N—CΘTRef.
(PhOH)(Et)(Et)1.491 (4)1.646 (4)118.6 (2)114.4 (4)199a
(Ph)(Me)(Me)1.4811.681117.5115.1b
(Ph)(Etn)1.4791.672117.659.8177c
(Ph)(Me)(PhEt)1.489 (1)1.646 (2)117.9 (1)114.0 (1)179d
(PhOMe)(Et)(Et)1.4731.654118.3114.3177e
Notes: (a) This work; (b) Ul-Haque & Caughlan (1976) (methyl H atoms not included in structure from CSD); (c) Davidowitz et al. (1985); (d) Cameron & Duncanson (1981); (e) Utenova et al. (1998). CSD data extracted from Cambridge Structural Database for a, b, c and d, no s.u. values available. ΘT = Tolman cone angle. Me = methyl, Et = ethyl, Ph = phenyl, PhOH = 2-hydroxyphenyl, Etn = ethylene, PhEt = phenylethyl.
 

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