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The title compound, C23H29NO4, has been obtained by a Grignard reaction of 3-tert-butyl 4-methyl (4S)-2,2-dimethyl­oxazolidine-3,4-dicarboxyl­ate with phenyl­magnesium bromide. An intra­molecular hydrogen bond occurs between the oxazole and hydr­oxy groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806033071/xu2111sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806033071/xu2111Isup2.hkl
Contains datablock I

CCDC reference: 625011

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.064
  • wR factor = 0.157
  • Data-to-parameter ratio = 9.8

checkCIF/PLATON results

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Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.00 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.80 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C21 - C22 .. 5.32 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 26.00 From the CIF: _reflns_number_total 2480 Count of symmetry unique reflns 2491 Completeness (_total/calc) 99.56% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 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 0 ALERT type 5 Informative message, check

Computing details top

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

(4S)-tert-Butyl 4-(hydroxydiphenylmethyl)-2,2-dimethyloxazolidine-3-carboxylate top
Crystal data top
C23H29NO4F(000) = 824
Mr = 383.47Dx = 1.163 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4105 reflections
a = 6.167 (2) Åθ = 2.3–24.7°
b = 17.497 (6) ŵ = 0.08 mm1
c = 20.288 (7) ÅT = 273 K
V = 2189.2 (13) Å3Chunk, colorless
Z = 40.48 × 0.25 × 0.11 mm
Data collection top
Bruker APEX area-detector
diffractometer
2480 independent reflections
Radiation source: fine-focus sealed tube2254 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
φ and ω scansθmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
h = 77
Tmin = 0.955, Tmax = 0.989k = 2120
11521 measured reflectionsl = 2125
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)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H-atom parameters constrained
S = 1.31 w = 1/[σ2(Fo2) + (0.0764P)2 + 0.0673P]
where P = (Fo2 + 2Fc2)/3
2480 reflections(Δ/σ)max < 0.001
253 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.24 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
O40.0012 (4)0.28710 (14)0.79700 (11)0.0467 (6)
H1D0.01650.31420.76440.070*
O10.2173 (5)0.36416 (12)0.69246 (12)0.0557 (7)
O20.5455 (5)0.13574 (14)0.71818 (11)0.0542 (7)
N10.3347 (5)0.24015 (14)0.69882 (11)0.0351 (6)
C180.2747 (6)0.29832 (16)0.88335 (14)0.0343 (7)
C110.2099 (5)0.25824 (17)0.81766 (14)0.0336 (7)
O30.3499 (4)0.14694 (13)0.62314 (10)0.0464 (6)
C40.3844 (6)0.27648 (16)0.76335 (14)0.0327 (7)
H21A0.52900.26130.77850.039*
C210.3716 (8)0.3649 (2)1.00641 (16)0.0544 (11)
H20A0.40260.38621.04730.065*
C50.3839 (8)0.36072 (18)0.74297 (17)0.0519 (10)
H19A0.34790.39340.78000.062*
H19B0.52380.37580.72550.062*
C130.0003 (7)0.1334 (2)0.80355 (18)0.0517 (9)
H18A0.10910.16180.78330.062*
C20.2419 (7)0.29738 (19)0.65099 (16)0.0445 (9)
C120.1844 (5)0.17068 (18)0.82732 (13)0.0345 (7)
C160.3212 (9)0.0477 (2)0.86366 (19)0.0588 (11)
H15A0.43080.01930.88350.071*
C190.1174 (6)0.33900 (18)0.91841 (16)0.0428 (8)
H14A0.02130.34420.90090.051*
C230.4844 (6)0.29368 (18)0.91040 (15)0.0395 (8)
H13A0.59330.26890.88700.047*
C60.4229 (6)0.17102 (18)0.68303 (15)0.0371 (7)
C220.5316 (7)0.3257 (2)0.97179 (15)0.0485 (9)
H11A0.66990.32090.98950.058*
C170.3434 (7)0.12649 (19)0.85734 (17)0.0476 (9)
H10A0.46750.15010.87360.057*
C150.1370 (8)0.0113 (2)0.8407 (2)0.0621 (12)
H9A0.12020.04120.84570.074*
C200.1664 (8)0.3721 (2)0.97976 (17)0.0542 (11)
H8A0.06010.39901.00260.065*
C30.3974 (8)0.3160 (2)0.59442 (18)0.0642 (12)
H7A0.53670.32940.61210.096*
H7B0.34110.35810.56940.096*
H7C0.41180.27210.56630.096*
C70.4180 (7)0.0718 (2)0.59701 (18)0.0510 (10)
C140.0238 (8)0.0548 (2)0.8097 (2)0.0664 (13)
H5A0.14710.03100.79310.080*
C10.0146 (7)0.2755 (2)0.6270 (2)0.0598 (11)
H4A0.07620.26450.66420.090*
H4B0.02390.23110.59930.090*
H4C0.04630.31710.60240.090*
C100.2990 (10)0.0689 (3)0.5300 (2)0.0814 (16)
H3A0.35430.10840.50180.122*
H3B0.14660.07660.53690.122*
H3C0.32240.02000.50980.122*
C90.3305 (11)0.0092 (2)0.6414 (2)0.0859 (18)
H2A0.17580.01410.64480.129*
H2B0.39420.01380.68440.129*
H2C0.36590.03980.62300.129*
C80.6622 (9)0.0694 (3)0.5882 (3)0.098 (2)
H1A0.70640.11010.55940.148*
H1B0.70330.02120.56920.148*
H1C0.73150.07530.63020.148*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.0416 (15)0.0564 (15)0.0423 (13)0.0101 (12)0.0070 (12)0.0000 (11)
O10.084 (2)0.0338 (12)0.0490 (14)0.0140 (13)0.0064 (15)0.0042 (10)
O20.0633 (18)0.0543 (15)0.0450 (13)0.0253 (14)0.0168 (13)0.0090 (11)
N10.0465 (17)0.0356 (13)0.0232 (12)0.0077 (12)0.0027 (12)0.0000 (10)
C180.047 (2)0.0289 (14)0.0267 (14)0.0021 (15)0.0042 (15)0.0013 (11)
C110.0340 (18)0.0389 (16)0.0278 (14)0.0001 (14)0.0028 (14)0.0029 (12)
O30.0635 (16)0.0464 (13)0.0294 (10)0.0144 (13)0.0082 (11)0.0081 (9)
C40.0380 (18)0.0316 (15)0.0284 (14)0.0022 (13)0.0095 (14)0.0021 (12)
C210.090 (3)0.0464 (19)0.0268 (16)0.024 (2)0.002 (2)0.0031 (14)
C50.077 (3)0.0373 (17)0.0419 (18)0.005 (2)0.0028 (19)0.0021 (14)
C130.052 (2)0.050 (2)0.053 (2)0.0070 (19)0.0066 (19)0.0069 (17)
C20.059 (2)0.0378 (16)0.0363 (17)0.0108 (18)0.0097 (18)0.0036 (13)
C120.0410 (19)0.0405 (16)0.0219 (13)0.0050 (15)0.0040 (14)0.0045 (12)
C160.082 (3)0.0416 (19)0.052 (2)0.000 (2)0.009 (2)0.0084 (16)
C190.048 (2)0.0402 (17)0.0401 (17)0.0012 (16)0.0098 (17)0.0000 (14)
C230.048 (2)0.0396 (16)0.0311 (15)0.0012 (17)0.0055 (16)0.0008 (13)
C60.0387 (18)0.0424 (17)0.0301 (15)0.0083 (15)0.0017 (15)0.0013 (13)
C220.061 (2)0.0498 (19)0.0346 (17)0.0115 (19)0.0067 (18)0.0003 (15)
C170.055 (2)0.0397 (18)0.048 (2)0.0084 (17)0.0154 (19)0.0029 (14)
C150.092 (4)0.0377 (18)0.056 (2)0.024 (2)0.005 (3)0.0026 (16)
C200.082 (3)0.0448 (19)0.0361 (18)0.005 (2)0.016 (2)0.0065 (15)
C30.081 (3)0.070 (3)0.043 (2)0.003 (2)0.006 (2)0.0207 (19)
C70.062 (3)0.048 (2)0.0426 (19)0.0115 (18)0.0040 (19)0.0161 (16)
C140.073 (3)0.058 (2)0.068 (3)0.031 (2)0.008 (3)0.012 (2)
C10.061 (3)0.065 (2)0.053 (2)0.022 (2)0.020 (2)0.0021 (19)
C100.114 (5)0.085 (3)0.046 (2)0.010 (3)0.014 (3)0.028 (2)
C90.126 (5)0.051 (2)0.081 (3)0.002 (3)0.014 (3)0.002 (2)
C80.075 (4)0.116 (5)0.104 (4)0.020 (3)0.013 (3)0.058 (4)
Geometric parameters (Å, º) top
O4—C111.445 (4)C16—H15A0.9300
O4—H1D0.8200C19—C201.406 (5)
O1—C21.448 (4)C19—H14A0.9300
O1—C51.452 (5)C23—C221.397 (4)
O2—C61.209 (4)C23—H13A0.9300
N1—C61.364 (4)C22—H11A0.9300
N1—C41.487 (4)C17—H10A0.9300
N1—C21.507 (4)C15—C141.399 (7)
C18—C191.398 (5)C15—H9A0.9300
C18—C231.407 (5)C20—H8A0.9300
C18—C111.558 (4)C3—H7A0.9600
C11—C121.553 (4)C3—H7B0.9600
C11—C41.573 (5)C3—H7C0.9600
O3—C61.363 (4)C7—C91.516 (6)
O3—C71.479 (4)C7—C81.517 (7)
C4—C51.531 (4)C7—C101.546 (6)
C4—H21A0.9800C14—H5A0.9300
C21—C201.381 (7)C1—H4A0.9600
C21—C221.392 (6)C1—H4B0.9600
C21—H20A0.9300C1—H4C0.9600
C5—H19A0.9700C10—H3A0.9600
C5—H19B0.9700C10—H3B0.9600
C13—C141.389 (5)C10—H3C0.9600
C13—C121.398 (5)C9—H2A0.9600
C13—H18A0.9300C9—H2B0.9600
C2—C31.531 (5)C9—H2C0.9600
C2—C11.533 (6)C8—H1A0.9600
C12—C171.389 (5)C8—H1B0.9600
C16—C151.383 (6)C8—H1C0.9600
C16—C171.392 (5)
C11—O4—H1D109.5O3—C6—N1110.6 (3)
C2—O1—C5107.6 (3)C21—C22—C23120.0 (4)
C6—N1—C4120.2 (3)C21—C22—H11A120.0
C6—N1—C2126.1 (2)C23—C22—H11A120.0
C4—N1—C2111.2 (2)C12—C17—C16121.5 (4)
C19—C18—C23118.0 (3)C12—C17—H10A119.3
C19—C18—C11119.1 (3)C16—C17—H10A119.3
C23—C18—C11122.9 (3)C16—C15—C14118.9 (3)
O4—C11—C12106.9 (3)C16—C15—H9A120.6
O4—C11—C18108.6 (3)C14—C15—H9A120.6
C12—C11—C18111.2 (2)C21—C20—C19120.4 (4)
O4—C11—C4109.6 (2)C21—C20—H8A119.8
C12—C11—C4111.0 (2)C19—C20—H8A119.8
C18—C11—C4109.4 (2)C2—C3—H7A109.5
C6—O3—C7120.0 (3)C2—C3—H7B109.5
N1—C4—C5100.0 (2)H7A—C3—H7B109.5
N1—C4—C11112.9 (3)C2—C3—H7C109.5
C5—C4—C11112.5 (3)H7A—C3—H7C109.5
N1—C4—H21A110.4H7B—C3—H7C109.5
C5—C4—H21A110.4O3—C7—C9109.1 (3)
C11—C4—H21A110.4O3—C7—C8110.4 (4)
C20—C21—C22119.8 (3)C9—C7—C8113.8 (5)
C20—C21—H20A120.1O3—C7—C10102.0 (3)
C22—C21—H20A120.1C9—C7—C10109.3 (4)
O1—C5—C4103.4 (3)C8—C7—C10111.5 (4)
O1—C5—H19A111.1C13—C14—C15120.4 (4)
C4—C5—H19A111.1C13—C14—H5A119.8
O1—C5—H19B111.1C15—C14—H5A119.8
C4—C5—H19B111.1C2—C1—H4A109.5
H19A—C5—H19B109.0C2—C1—H4B109.5
C14—C13—C12121.1 (4)H4A—C1—H4B109.5
C14—C13—H18A119.5C2—C1—H4C109.5
C12—C13—H18A119.5H4A—C1—H4C109.5
O1—C2—N1101.6 (2)H4B—C1—H4C109.5
O1—C2—C3109.3 (3)C7—C10—H3A109.5
N1—C2—C3112.7 (3)C7—C10—H3B109.5
O1—C2—C1106.9 (3)H3A—C10—H3B109.5
N1—C2—C1112.7 (3)C7—C10—H3C109.5
C3—C2—C1112.8 (3)H3A—C10—H3C109.5
C17—C12—C13117.8 (3)H3B—C10—H3C109.5
C17—C12—C11122.2 (3)C7—C9—H2A109.5
C13—C12—C11119.9 (3)C7—C9—H2B109.5
C15—C16—C17120.4 (4)H2A—C9—H2B109.5
C15—C16—H15A119.8C7—C9—H2C109.5
C17—C16—H15A119.8H2A—C9—H2C109.5
C18—C19—C20120.7 (4)H2B—C9—H2C109.5
C18—C19—H14A119.6C7—C8—H1A109.5
C20—C19—H14A119.6C7—C8—H1B109.5
C22—C23—C18121.1 (3)H1A—C8—H1B109.5
C22—C23—H13A119.5C7—C8—H1C109.5
C18—C23—H13A119.5H1A—C8—H1C109.5
O2—C6—O3125.1 (3)H1B—C8—H1C109.5
O2—C6—N1124.3 (3)
 

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