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The title compound, C21H14O4, containing three chiral C atoms, is a key inter­mediate in the design of chiral alcohols. Racemic dimers are generated by C—H...O hydrogen bonds formed between phen­yl C—H groups and ep­oxy O atoms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805010378/sj6065sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805010378/sj6065Isup2.hkl
Contains datablock I

CCDC reference: 272111

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.044
  • wR factor = 0.137
  • Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 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, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

(I) top
Crystal data top
C21H14O4F(000) = 688
Mr = 330.32Dx = 1.419 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4328 reflections
a = 10.5756 (6) Åθ = 2.9–25.1°
b = 10.5907 (6) ŵ = 0.10 mm1
c = 14.4795 (8) ÅT = 293 K
β = 107.548 (1)°Block, colourless
V = 1546.28 (15) Å30.47 × 0.45 × 0.23 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2918 reflections with I > 2σ(I)
φ and ω scansRint = 0.022
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
θmax = 28.0°, θmin = 2.4°
Tmin = 0.963, Tmax = 0.987h = 1313
10025 measured reflectionsk = 1310
3717 independent reflectionsl = 1919
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullOnly H-atom displacement parameters refined
R[F2 > 2σ(F2)] = 0.044 w = 1/[σ2(Fo2) + (0.0789P)2 + 0.1717P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.137(Δ/σ)max = 0.001
S = 1.05Δρmax = 0.31 e Å3
3717 reflectionsΔρmin = 0.22 e Å3
226 parameters
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.77165 (13)0.81851 (10)0.18396 (8)0.0638 (3)
O20.98001 (10)0.54251 (11)0.21628 (8)0.0550 (3)
O30.62251 (11)0.36982 (10)0.29165 (8)0.0521 (3)
O40.65758 (9)0.60111 (8)0.09972 (6)0.0396 (2)
C10.64455 (14)0.49214 (14)0.32260 (10)0.0452 (3)
C20.60597 (16)0.52300 (18)0.40357 (11)0.0591 (4)
H2A0.56210.4640.43040.071*
C30.63294 (19)0.6407 (2)0.44343 (12)0.0671 (5)
H3A0.60710.6620.49740.081*
C40.69841 (18)0.72797 (18)0.40370 (12)0.0636 (5)
H4A0.71750.80740.43190.076*
C50.73619 (15)0.69906 (15)0.32222 (10)0.0500 (4)
C60.81599 (18)0.78986 (15)0.28536 (12)0.0579 (4)
H6A0.85720.85920.32890.069*
C70.88910 (16)0.74344 (14)0.21995 (11)0.0531 (4)
H7A0.9740.78410.22450.064*
C80.88024 (13)0.60379 (13)0.20363 (9)0.0409 (3)
C90.74192 (12)0.54395 (12)0.18732 (8)0.0345 (3)
C100.70572 (13)0.57914 (13)0.27833 (9)0.0399 (3)
C110.74153 (11)0.40225 (12)0.17420 (9)0.0348 (3)
C120.79392 (12)0.34325 (12)0.10356 (9)0.0369 (3)
C130.83876 (14)0.41179 (14)0.03513 (10)0.0444 (3)
H13A0.83170.49940.03320.053*
C140.89218 (16)0.35140 (18)0.02810 (12)0.0581 (4)
H14A0.91940.39840.07290.07*
C150.90629 (18)0.21989 (19)0.02609 (13)0.0656 (5)
H15A0.94670.18010.06710.079*
C160.86032 (17)0.15047 (16)0.03646 (13)0.0581 (4)
H16A0.8690.06310.03730.07*
C170.79968 (13)0.20915 (13)0.09999 (10)0.0434 (3)
C180.74296 (15)0.13634 (14)0.15959 (11)0.0500 (4)
H18A0.74640.04870.15730.06*
C190.68406 (15)0.19230 (14)0.21952 (12)0.0503 (4)
H19A0.64340.14360.25590.06*
C200.68437 (13)0.32559 (13)0.22677 (10)0.0414 (3)
C210.52142 (14)0.60914 (17)0.09210 (11)0.0555 (4)
H21A0.47440.64850.03180.083*
H21B0.51060.65860.14480.083*
H21C0.48680.52580.09450.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0886 (9)0.0331 (6)0.0608 (7)0.0007 (5)0.0090 (6)0.0016 (5)
O20.0379 (5)0.0572 (7)0.0671 (7)0.0044 (4)0.0114 (4)0.0093 (5)
O30.0591 (6)0.0465 (6)0.0607 (6)0.0047 (5)0.0332 (5)0.0029 (5)
O40.0409 (5)0.0380 (5)0.0371 (4)0.0035 (4)0.0073 (3)0.0043 (4)
C10.0447 (7)0.0492 (8)0.0430 (7)0.0063 (6)0.0151 (6)0.0033 (6)
C20.0591 (9)0.0749 (11)0.0500 (8)0.0127 (8)0.0265 (7)0.0067 (8)
C30.0718 (11)0.0853 (13)0.0474 (8)0.0181 (10)0.0228 (8)0.0082 (8)
C40.0729 (11)0.0627 (11)0.0501 (8)0.0115 (8)0.0107 (8)0.0191 (8)
C50.0548 (8)0.0456 (8)0.0440 (7)0.0054 (6)0.0063 (6)0.0078 (6)
C60.0744 (10)0.0368 (8)0.0539 (8)0.0047 (7)0.0065 (7)0.0104 (6)
C70.0599 (9)0.0373 (8)0.0569 (8)0.0130 (7)0.0097 (7)0.0019 (6)
C80.0427 (7)0.0393 (7)0.0386 (6)0.0069 (5)0.0092 (5)0.0011 (5)
C90.0361 (6)0.0309 (6)0.0352 (6)0.0003 (5)0.0088 (4)0.0014 (4)
C100.0422 (6)0.0396 (7)0.0359 (6)0.0042 (5)0.0088 (5)0.0007 (5)
C110.0334 (6)0.0308 (6)0.0382 (6)0.0010 (4)0.0079 (5)0.0011 (5)
C120.0327 (6)0.0345 (6)0.0403 (6)0.0019 (5)0.0064 (5)0.0026 (5)
C130.0453 (7)0.0450 (8)0.0433 (7)0.0042 (6)0.0138 (5)0.0026 (6)
C140.0577 (9)0.0704 (11)0.0512 (8)0.0083 (8)0.0241 (7)0.0099 (7)
C150.0664 (10)0.0699 (12)0.0676 (10)0.0018 (9)0.0308 (9)0.0245 (9)
C160.0573 (9)0.0445 (8)0.0690 (10)0.0018 (7)0.0138 (7)0.0198 (7)
C170.0387 (6)0.0366 (7)0.0495 (7)0.0005 (5)0.0050 (5)0.0058 (5)
C180.0528 (8)0.0285 (6)0.0632 (9)0.0039 (6)0.0089 (7)0.0005 (6)
C190.0533 (8)0.0369 (7)0.0612 (9)0.0083 (6)0.0178 (7)0.0075 (6)
C200.0409 (6)0.0382 (7)0.0454 (7)0.0018 (5)0.0137 (5)0.0021 (5)
C210.0420 (7)0.0672 (11)0.0517 (8)0.0099 (7)0.0057 (6)0.0010 (7)
Geometric parameters (Å, º) top
O1—C61.433 (2)C9—C111.5126 (17)
O1—C71.434 (2)C9—C101.5251 (17)
O2—C81.2049 (17)C11—C201.3716 (18)
O3—C11.3676 (18)C11—C121.4441 (18)
O3—C201.3786 (17)C12—C131.4201 (19)
O4—C211.4131 (17)C12—C171.4230 (19)
O4—C91.4452 (14)C13—C141.371 (2)
C1—C101.389 (2)C13—H13A0.93
C1—C21.391 (2)C14—C151.400 (3)
C2—C31.367 (3)C14—H14A0.93
C2—H2A0.93C15—C161.365 (3)
C3—C41.380 (3)C15—H15A0.93
C3—H3A0.93C16—C171.414 (2)
C4—C51.389 (2)C16—H16A0.93
C4—H4A0.93C17—C181.418 (2)
C5—C101.413 (2)C18—C191.349 (2)
C5—C61.481 (2)C18—H18A0.93
C6—C71.476 (2)C19—C201.415 (2)
C6—H6A0.98C19—H19A0.93
C7—C81.496 (2)C21—H21A0.96
C7—H7A0.98C21—H21B0.96
C8—C91.5456 (17)C21—H21C0.96
C6—O1—C761.97 (11)C1—C10—C5117.61 (13)
C1—O3—C20118.43 (11)C1—C10—C9120.66 (12)
C21—O4—C9116.01 (10)C5—C10—C9121.70 (12)
O3—C1—C10122.30 (12)C20—C11—C12117.67 (12)
O3—C1—C2115.74 (14)C20—C11—C9120.17 (11)
C10—C1—C2121.93 (15)C12—C11—C9122.08 (11)
C3—C2—C1119.54 (17)C13—C12—C17117.25 (12)
C3—C2—H2A120.2C13—C12—C11123.58 (12)
C1—C2—H2A120.2C17—C12—C11119.16 (12)
C2—C3—C4120.12 (15)C14—C13—C12121.27 (14)
C2—C3—H3A119.9C14—C13—H13A119.4
C4—C3—H3A119.9C12—C13—H13A119.4
C3—C4—C5121.01 (16)C13—C14—C15120.88 (16)
C3—C4—H4A119.5C13—C14—H14A119.6
C5—C4—H4A119.5C15—C14—H14A119.6
C4—C5—C10119.68 (15)C16—C15—C14119.51 (15)
C4—C5—C6120.26 (14)C16—C15—H15A120.2
C10—C5—C6119.93 (13)C14—C15—H15A120.2
O1—C6—C759.06 (11)C15—C16—C17121.14 (15)
O1—C6—C5117.44 (13)C15—C16—H16A119.4
C7—C6—C5118.73 (13)C17—C16—H16A119.4
O1—C6—H6A116.4C16—C17—C18120.99 (14)
C7—C6—H6A116.4C16—C17—C12119.67 (14)
C5—C6—H6A116.4C18—C17—C12119.34 (13)
O1—C7—C658.97 (10)C19—C18—C17120.98 (13)
O1—C7—C8118.98 (12)C19—C18—H18A119.5
C6—C7—C8114.25 (13)C17—C18—H18A119.5
O1—C7—H7A117.2C18—C19—C20119.66 (13)
C6—C7—H7A117.2C18—C19—H19A120.2
C8—C7—H7A117.2C20—C19—H19A120.2
O2—C8—C7119.88 (12)C11—C20—O3123.79 (12)
O2—C8—C9123.19 (12)C11—C20—C19122.73 (13)
C7—C8—C9116.15 (12)O3—C20—C19113.48 (12)
O4—C9—C11109.13 (9)O4—C21—H21A109.5
O4—C9—C10113.99 (10)O4—C21—H21B109.5
C11—C9—C10111.04 (10)H21A—C21—H21B109.5
O4—C9—C8105.52 (9)O4—C21—H21C109.5
C11—C9—C8113.12 (10)H21A—C21—H21C109.5
C10—C9—C8103.91 (10)H21B—C21—H21C109.5
C20—O3—C1—C1012.27 (19)O4—C9—C10—C1106.68 (13)
C20—O3—C1—C2165.57 (13)C11—C9—C10—C117.08 (16)
O3—C1—C2—C3175.39 (14)C8—C9—C10—C1138.99 (12)
C10—C1—C2—C32.5 (2)O4—C9—C10—C575.19 (15)
C1—C2—C3—C40.2 (3)C11—C9—C10—C5161.06 (12)
C2—C3—C4—C51.0 (3)C8—C9—C10—C539.14 (15)
C3—C4—C5—C100.9 (2)O4—C9—C11—C20112.43 (12)
C3—C4—C5—C6174.94 (15)C10—C9—C11—C2014.06 (16)
C7—O1—C6—C5108.67 (15)C8—C9—C11—C20130.44 (12)
C4—C5—C6—O1130.95 (16)O4—C9—C11—C1264.28 (14)
C10—C5—C6—O153.2 (2)C10—C9—C11—C12169.23 (10)
C4—C5—C6—C7161.15 (14)C8—C9—C11—C1252.85 (15)
C10—C5—C6—C714.7 (2)C20—C11—C12—C13170.93 (12)
C6—O1—C7—C8102.39 (15)C9—C11—C12—C135.86 (18)
C5—C6—C7—O1106.50 (15)C20—C11—C12—C177.94 (17)
O1—C6—C7—C8110.44 (14)C9—C11—C12—C17175.27 (11)
C5—C6—C7—C83.9 (2)C17—C12—C13—C143.54 (19)
O1—C7—C8—O2165.86 (13)C11—C12—C13—C14177.57 (13)
C6—C7—C8—O2127.52 (15)C12—C13—C14—C151.1 (2)
O1—C7—C8—C923.89 (18)C13—C14—C15—C163.2 (3)
C6—C7—C8—C942.73 (17)C14—C15—C16—C170.6 (3)
C21—O4—C9—C1186.08 (13)C15—C16—C17—C18175.13 (15)
C21—O4—C9—C1038.70 (15)C15—C16—C17—C124.1 (2)
C21—O4—C9—C8152.07 (12)C13—C12—C17—C166.05 (19)
O2—C8—C9—O4127.70 (13)C11—C12—C17—C16175.01 (12)
C7—C8—C9—O462.40 (13)C13—C12—C17—C18173.23 (12)
O2—C8—C9—C118.47 (17)C11—C12—C17—C185.72 (18)
C7—C8—C9—C11178.36 (11)C16—C17—C18—C19179.39 (14)
O2—C8—C9—C10112.06 (14)C12—C17—C18—C190.1 (2)
C7—C8—C9—C1057.83 (14)C17—C18—C19—C203.1 (2)
O3—C1—C10—C5173.50 (13)C12—C11—C20—O3175.40 (12)
C2—C1—C10—C54.2 (2)C9—C11—C20—O31.45 (19)
O3—C1—C10—C94.7 (2)C12—C11—C20—C194.88 (19)
C2—C1—C10—C9177.58 (13)C9—C11—C20—C19178.27 (12)
C4—C5—C10—C13.4 (2)C1—O3—C20—C1115.67 (19)
C6—C5—C10—C1172.46 (13)C1—O3—C20—C19164.07 (12)
C4—C5—C10—C9178.44 (13)C18—C19—C20—C110.7 (2)
C6—C5—C10—C95.7 (2)C18—C19—C20—O3179.09 (13)
 

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