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The tetra­hydro­furan ring in trans-4R(S)-phenyl­tetra­hydro-2R(S)-furyl­methyl p-nitro­benzoate, C18H17NO5, adopts a 1T5 conformation in the solid state. The phenyl group and the functionalized CH2 substituent are located in pseudo-equatorial positions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803027028/ya6180sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803027028/ya6180Isup2.hkl
Contains datablock I

CCDC reference: 232130

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.074
  • wR factor = 0.244
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C ABSMU01_ALERT_1_C The ratio of given/expected absorption coefficient lies outside the range 0.99 <> 1.01 Calculated value of mu = 0.098 Value of mu given = 0.100 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.75 mm PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms ..... 1 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... N1 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C7 PLAT331_ALERT_2_C Small Av. Phenyl C-C Dist. C7 - C12 = 1.37 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C2 - C6 = 1.41 Ang. PLAT751_ALERT_4_C Bond Calc 1.41259, Rep 1.412(3) ...... Senseless su C5 -O1 1.555 1.555 PLAT752_ALERT_4_C Angle Calc 104.29, Rep 104.25(18) ...... Senseless su C3 -C4 -C5 1.555 1.555 1.555 PLAT752_ALERT_4_C Angle Calc 115.45, Rep 115.50(15) ...... Senseless su C5 -C4 -C7 1.555 1.555 1.555 PLAT752_ALERT_4_C Angle Calc 104.74, Rep 104.79(14) ...... Senseless su O1 -C5 -C4 1.555 1.555 1.555 PLAT752_ALERT_4_C Angle Calc 106.00, Rep 106.0(2) ...... Senseless su C5 -O1 -C2 1.555 1.555 1.555 PLAT753_ALERT_4_C Torsion Calc 16.04, Rep 16.0(4) ...... Senseless su C2 -C3 -C4 -C5 1.555 1.555 1.555 1.555 PLAT753_ALERT_4_C Torsion Calc -33.98, Rep -34.0(2) ...... Senseless su C3 -C4 -C5 -O1 1.555 1.555 1.555 1.555 PLAT753_ALERT_4_C Torsion Calc -166.61, Rep -166.6(3) ...... Senseless su C7 -C4 -C5 -O1 1.555 1.555 1.555 1.555 PLAT753_ALERT_4_C Torsion Calc -101.44, Rep -101.5(3) ...... Senseless su C5 -C4 -C7 -C12 1.555 1.555 1.555 1.555 PLAT753_ALERT_4_C Torsion Calc 78.57, Rep 78.6(3) ...... Senseless su C5 -C4 -C7 -C8 1.555 1.555 1.555 1.555 PLAT753_ALERT_4_C Torsion Calc 39.10, Rep 39.1(3) ...... Senseless su C4 -C5 -O1 -C2 1.555 1.555 1.555 1.555 PLAT753_ALERT_4_C Torsion Calc -151.99, Rep -152.0(4) ...... Senseless su C6 -C2 -O1 -C5 1.555 1.555 1.555 1.555 PLAT753_ALERT_4_C Torsion Calc -28.39, Rep -28.3(5) ...... Senseless su C3 -C2 -O1 -C5 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 22 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 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 14 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Diffractometer Control Software (Enraf-Nonius, 1993); cell refinement: CAD-4 Diffractometer Control Software; data reduction: CAD-4 Diffractometer Control Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

trans-(4-Phenyltetrahydro-2-furyl)methyl p-nitrobenzoate top
Crystal data top
C18H17NO5Dx = 1.326 Mg m3
Mr = 327.33Melting point: 324 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 6.993 (1) ÅCell parameters from 25 reflections
b = 14.490 (2) Åθ = 3.6–12.8°
c = 16.274 (3) ŵ = 0.10 mm1
β = 96.07 (2)°T = 299 K
V = 1639.8 (4) Å3Prism, colourless
Z = 40.75 × 0.60 × 0.43 mm
F(000) = 688
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.051
Radiation source: fine-focus sealed tubeθmax = 26.0°, θmin = 1.9°
Graphite monochromatorh = 81
ω/2θ scansk = 170
3886 measured reflectionsl = 2020
3212 independent reflections3 standard reflections every 120 min
2250 reflections with I > 2σ(I) intensity decay: 2.2%
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)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.244H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.1114P)2 + 0.9016P]
where P = (Fo2 + 2Fc2)/3
3212 reflections(Δ/σ)max = 0.004
215 parametersΔρmax = 0.60 e Å3
0 restraintsΔρmin = 0.36 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
C20.3889 (7)0.9062 (3)0.1955 (2)0.1037 (13)
H20.28470.86100.18660.124*
C30.4517 (6)0.9346 (3)0.1117 (2)0.1018 (14)
H3A0.36340.91050.06690.122*
H3B0.45651.00130.10690.122*
C40.6441 (5)0.8944 (2)0.10999 (14)0.0880 (11)
H40.73480.94340.12890.106*
C50.6587 (5)0.8245 (2)0.17760 (14)0.1020 (14)
H5A0.60330.76620.15800.122*
H5B0.79180.81450.19910.122*
C60.3276 (7)0.9802 (3)0.2425 (2)0.1011 (14)
H6A0.21371.00820.21360.121*
H6B0.42771.02670.24970.121*
C70.7055 (5)0.8616 (2)0.02853 (17)0.0720 (9)
C80.5931 (6)0.8076 (3)0.0278 (2)0.0939 (12)
H80.47160.78900.01620.113*
C90.6595 (8)0.7813 (3)0.1010 (2)0.1093 (15)
H90.58300.74470.13810.131*
C100.8340 (8)0.8082 (3)0.1190 (2)0.0997 (13)
H100.87680.79140.16910.120*
C110.9446 (6)0.8585 (3)0.0658 (3)0.0971 (12)
H111.06640.87570.07820.117*
C120.8826 (6)0.8862 (3)0.0083 (2)0.0838 (10)
H120.96270.92200.04470.101*
C130.2772 (4)1.0107 (2)0.3796 (2)0.0705 (8)
C140.2448 (3)0.9712 (2)0.46180 (18)0.0604 (7)
C150.2586 (4)1.0303 (2)0.5286 (2)0.0659 (7)
H150.28851.09210.52150.079*
C160.2284 (4)0.9984 (2)0.60607 (19)0.0687 (8)
H160.23891.03780.65140.082*
C170.1824 (4)0.9068 (2)0.61448 (18)0.0647 (7)
C180.1672 (4)0.8466 (2)0.5492 (2)0.0720 (8)
H180.13590.78500.55660.086*
C190.1992 (4)0.8793 (2)0.4721 (2)0.0686 (8)
H190.19020.83950.42700.082*
N10.1497 (4)0.8720 (2)0.69681 (19)0.0826 (8)
O10.5537 (4)0.86273 (19)0.23888 (13)0.1015 (10)
O20.2848 (4)0.94652 (18)0.32287 (14)0.0865 (7)
O30.2959 (4)1.09144 (19)0.36656 (18)0.0993 (8)
O40.1158 (5)0.7907 (2)0.70411 (19)0.1182 (11)
O50.1539 (5)0.9275 (3)0.75342 (17)0.1200 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.121 (3)0.123 (3)0.071 (2)0.040 (3)0.027 (2)0.016 (2)
C30.122 (3)0.122 (3)0.064 (2)0.057 (3)0.0274 (19)0.024 (2)
C40.119 (3)0.088 (2)0.0587 (18)0.023 (2)0.0167 (17)0.0023 (16)
C50.151 (4)0.103 (3)0.0556 (17)0.063 (3)0.028 (2)0.0134 (17)
C60.122 (3)0.114 (3)0.074 (2)0.047 (2)0.041 (2)0.026 (2)
C70.107 (3)0.0610 (17)0.0493 (15)0.0138 (16)0.0153 (15)0.0032 (13)
C80.122 (3)0.078 (2)0.086 (2)0.024 (2)0.034 (2)0.0093 (19)
C90.169 (5)0.085 (3)0.076 (2)0.022 (3)0.024 (3)0.025 (2)
C100.148 (4)0.094 (3)0.064 (2)0.019 (3)0.041 (2)0.0035 (19)
C110.098 (3)0.105 (3)0.092 (3)0.016 (2)0.032 (2)0.023 (2)
C120.090 (2)0.082 (2)0.077 (2)0.0030 (18)0.0030 (18)0.0033 (17)
C130.0529 (15)0.081 (2)0.081 (2)0.0144 (14)0.0250 (14)0.0067 (17)
C140.0422 (13)0.0693 (17)0.0727 (17)0.0071 (12)0.0205 (12)0.0036 (14)
C150.0486 (14)0.0658 (16)0.086 (2)0.0021 (12)0.0182 (13)0.0027 (15)
C160.0526 (15)0.082 (2)0.0731 (18)0.0006 (14)0.0156 (13)0.0120 (15)
C170.0500 (14)0.0784 (19)0.0689 (17)0.0082 (13)0.0215 (12)0.0030 (14)
C180.0748 (19)0.0630 (17)0.083 (2)0.0077 (14)0.0297 (16)0.0058 (15)
C190.0692 (18)0.0668 (18)0.0734 (18)0.0090 (14)0.0239 (14)0.0046 (14)
N10.0730 (17)0.100 (2)0.0797 (19)0.0087 (15)0.0309 (14)0.0083 (17)
O10.149 (2)0.1042 (19)0.0568 (12)0.0619 (17)0.0349 (13)0.0224 (12)
O20.0984 (17)0.0947 (17)0.0722 (14)0.0203 (13)0.0356 (12)0.0115 (12)
O30.113 (2)0.0807 (17)0.111 (2)0.0087 (14)0.0451 (15)0.0230 (15)
O40.159 (3)0.096 (2)0.109 (2)0.0216 (19)0.058 (2)0.0303 (17)
O50.141 (3)0.147 (3)0.0790 (17)0.036 (2)0.0445 (17)0.0165 (18)
Geometric parameters (Å, º) top
C2—C61.408 (6)C10—C111.318 (6)
C2—O11.432 (5)C10—H100.9300
C2—C31.532 (5)C11—C121.382 (6)
C2—H20.9800C11—H110.9300
C3—C41.470 (5)C12—H120.9300
C3—H3A0.9700C13—O31.199 (4)
C3—H3B0.9700C13—O21.316 (4)
C4—C51.4903C13—C141.493 (4)
C4—C71.512 (3)C14—C151.379 (4)
C4—H40.9800C14—C191.384 (4)
C5—O11.412 (3)C15—C161.379 (4)
C5—H5A0.9700C15—H150.9300
C5—H5B0.9700C16—C171.376 (5)
C6—O21.457 (4)C16—H160.9300
C6—H6A0.9700C17—C181.370 (4)
C6—H6B0.9700C17—N11.472 (4)
C7—C121.362 (5)C18—C191.382 (4)
C7—C81.385 (5)C18—H180.9300
C8—C91.376 (5)C19—H190.9300
C8—H80.9300N1—O41.210 (4)
C9—C101.343 (6)N1—O51.221 (4)
C9—H90.9300
C6—C2—O1110.0 (4)C10—C9—H9119.8
C6—C2—C3114.3 (4)C8—C9—H9119.8
O1—C2—C3105.4 (3)C11—C10—C9120.0 (4)
C6—C2—H2109.0C11—C10—H10120.0
O1—C2—H2109.0C9—C10—H10120.0
C3—C2—H2109.0C10—C11—C12121.1 (4)
C4—C3—C2105.1 (3)C10—C11—H11119.4
C4—C3—H3A110.7C12—C11—H11119.4
C2—C3—H3A110.7C7—C12—C11120.8 (4)
C4—C3—H3B110.7C7—C12—H12119.6
C2—C3—H3B110.7C11—C12—H12119.6
H3A—C3—H3B108.8O3—C13—O2123.5 (3)
C3—C4—C5104.25 (18)O3—C13—C14124.2 (3)
C3—C4—C7119.1 (3)O2—C13—C14112.3 (3)
C5—C4—C7115.50 (15)C15—C14—C19120.0 (3)
C3—C4—H4105.6C15—C14—C13117.7 (3)
C5—C4—H4105.6C19—C14—C13122.3 (3)
C7—C4—H4105.6C16—C15—C14120.5 (3)
O1—C5—C4104.79 (14)C16—C15—H15119.7
O1—C5—H5A110.8C14—C15—H15119.7
C4—C5—H5A110.8C17—C16—C15118.3 (3)
O1—C5—H5B110.8C17—C16—H16120.8
C4—C5—H5B110.8C15—C16—H16120.8
H5A—C5—H5B108.9C18—C17—C16122.4 (3)
C2—C6—O2109.6 (3)C18—C17—N1118.8 (3)
C2—C6—H6A109.7C16—C17—N1118.7 (3)
O2—C6—H6A109.7C17—C18—C19118.7 (3)
C2—C6—H6B109.7C17—C18—H18120.7
O2—C6—H6B109.7C19—C18—H18120.7
H6A—C6—H6B108.2C18—C19—C14120.1 (3)
C12—C7—C8117.0 (3)C18—C19—H19120.0
C12—C7—C4118.6 (3)C14—C19—H19120.0
C8—C7—C4124.3 (3)O4—N1—O5123.8 (3)
C9—C8—C7120.6 (4)O4—N1—C17118.3 (3)
C9—C8—H8119.7O5—N1—C17117.9 (3)
C7—C8—H8119.7C5—O1—C2106.0 (2)
C10—C9—C8120.4 (4)C13—O2—C6114.9 (3)
C6—C2—C3—C4127.6 (4)O3—C13—C14—C19171.5 (3)
O1—C2—C3—C46.7 (5)O2—C13—C14—C199.2 (4)
C2—C3—C4—C516.0 (4)C19—C14—C15—C160.4 (4)
C2—C3—C4—C7146.6 (3)C13—C14—C15—C16179.3 (2)
C3—C4—C5—O134.0 (2)C14—C15—C16—C170.7 (4)
C7—C4—C5—O1166.6 (3)C15—C16—C17—C180.5 (4)
O1—C2—C6—O257.6 (5)C15—C16—C17—N1179.9 (2)
C3—C2—C6—O2175.9 (3)C16—C17—C18—C190.0 (4)
C3—C4—C7—C12133.3 (4)N1—C17—C18—C19179.6 (3)
C5—C4—C7—C12101.5 (3)C17—C18—C19—C140.3 (4)
C3—C4—C7—C846.7 (5)C15—C14—C19—C180.1 (4)
C5—C4—C7—C878.6 (3)C13—C14—C19—C18178.8 (3)
C12—C7—C8—C90.4 (6)C18—C17—N1—O42.1 (4)
C4—C7—C8—C9179.5 (3)C16—C17—N1—O4177.5 (3)
C7—C8—C9—C100.5 (7)C18—C17—N1—O5176.2 (3)
C8—C9—C10—C111.4 (7)C16—C17—N1—O54.2 (4)
C9—C10—C11—C121.4 (7)C4—C5—O1—C239.1 (3)
C8—C7—C12—C110.4 (5)C6—C2—O1—C5152.0 (4)
C4—C7—C12—C11179.5 (3)C3—C2—O1—C528.3 (5)
C10—C11—C12—C70.5 (6)O3—C13—O2—C62.9 (5)
O3—C13—C14—C157.5 (4)C14—C13—O2—C6176.5 (3)
O2—C13—C14—C15171.9 (2)C2—C6—O2—C13162.3 (4)
 

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