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The title compound, C20H25NO2, a condensation product of l-ephedrine and 4-propoxy­aldehyde, is of interest in studies on weak interactions. It crystallizes with C—H...O and C—H...π(arene) intermolecular interactions as a one-dimensional chain [C...O = 3.3745 (19) Å, C—H...O = 139°; C—H...Cg1 = 3.6987 (16) Å, C—H...Cg1 = 161°, where Cg1 is the centroid of the symmetry-related 4-propoxy-substituted aromatic ring].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803028733/cf6304sup1.cif
Contains datablocks global, IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803028733/cf6304IVsup2.hkl
Contains datablock IV

CCDC reference: 234890

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.031
  • wR factor = 0.079
  • Data-to-parameter ratio = 10.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H23 .. CG1 = 2.79 Ang.
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 27.50 From the CIF: _reflns_number_total 2136 Count of symmetry unique reflns 2159 Completeness (_total/calc) 98.93% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PREP8 (Ferguson, 1998).

(2S,4S,5R)-(-)-2-(4-propoxyphenyl)-3,4-dimethyl-5-phenyl-1,3-oxazolidine top
Crystal data top
C20H25NO2F(000) = 336
Mr = 311.41Dx = 1.177 Mg m3
Monoclinic, P21Melting point: 344 K
Hall symbol: p_2ybMo Kα radiation, λ = 0.71073 Å
a = 9.2962 (2) ÅCell parameters from 14364 reflections
b = 8.2755 (2) Åθ = 2.6–27.5°
c = 11.4267 (3) ŵ = 0.08 mm1
β = 91.0830 (11)°T = 150 K
V = 878.91 (4) Å3Block, colourless
Z = 20.36 × 0.30 × 0.20 mm
Data collection top
Nonius KappaCCD
diffractometer
1988 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tubeRint = 0.036
Graphite monochromatorθmax = 27.5°, θmin = 3.0°
φ and ω scans with κ offsetsh = 1212
8081 measured reflectionsk = 910
2136 independent reflectionsl = 1314
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.079 w = 1/[σ2(Fo2) + (0.0392P)2 + 0.0616P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
2136 reflectionsΔρmax = 0.14 e Å3
212 parametersΔρmin = 0.11 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.068 (15)
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.

Cambridge Structural search on propoxyaromatic derivatives ———————————————————- Query Refcode ANG1 ANG2 TOR1 1 CIBCOF 114.243 124.847 20.268 1 DOVVEP 115.584 124.952 0.549 1 DOVVEP 116.417 124.358 - 0.309 1 FUNYOC 124.781 116.229 174.433 1 JILVUV 124.992 115.066 176.017 1 JILVUV 125.589 115.823 - 178.477 1 JULTUF 125.077 114.808 175.562 1 JULTUF 125.847 113.872 - 178.221 1 JULTUF 125.668 115.065 - 178.716 1 JULTUF 125.787 115.778 175.458 1 JULTUF01 125.330 115.567 179.724 1 JULTUF01 125.129 115.114 - 174.997 1 JULTUF01 124.846 115.194 - 176.362 1 JULTUF01 125.091 115.457 179.503 1 LONMEG 125.293 115.310 - 174.706 1 LONMIK 116.035 125.107 0.848 1 OCERAP 116.124 124.679 - 5.123 1 PEYGAB 116.025 124.493 - 2.659 1 PIGHUI 115.234 124.913 2.248 1 ZZZLAO10 123.895 115.843 - 179.157 1 XOSKUL 116.515 124.789 - 5.215 1 LUSFIO 115.101 125.458 - 4.903 1 LUSFIO 115.978 125.619 5.761

Specified hydrogen bonds (with e.s.d.'s except fixed and riding H) ————————————————————– D—H H···A D···A <(DHA)

0.95 2.99 3.750 (2) 138.1 C23—H23···C11_$2 0.95 2.95 3.663 (2) 133.0 C23—H23···C12_$2 0.95 3.10 3.884 (2) 141.4 C23—H23···C13_$2 0.95 3.25 4.152 (2) 159.1 C23—H23···C14_$2 0.95 3.26 4.205 (2) 174.3 C23—H23···C15_$2 0.95 3.14 4.017 (2) 155.1 C23—H23···C16_$2 0.95 2.60 3.374 (2) 139.0 C22—H22···O1_$2

Planes data ###########

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

5.4276(0.0049)x + 5.5914(0.0040)y + 5.0163(0.0064)z = 5.3766(0.0019)

* -0.0039(0.0010) C21 * 0.0037(0.0011) C22 * 0.0004(0.0011) C23 * -0.0042(0.0011) C24 * 0.0040(0.0012) C25 * 0.0001(0.0012) C26 - 0.0367(0.0024) C2 1.0033(0.0027) N3 - 0.0242(0.0022) O31

Rms deviation of fitted atoms = 0.0032

6.3817(0.0053)x - 4.9149(0.0065)y + 4.6448(0.0094)z = 2.0603(0.0054)

Angle to previous plane (with approximate e.s.d.) = 79.14 (5)

* 0.0677(0.0009) O1 * -0.0432(0.0005) C2 * 0.0392(0.0005) C4 * -0.0637(0.0008) C5 0.3018(0.0035) C31 0.8534(0.0031) C41 0.9774(0.0027) C11 0.6124(0.0026) C21 0.6017(0.0021) N3 2.4693(0.0051) O31

Rms deviation of fitted atoms = 0.0549

7.5676(0.0039)x + 4.7708(0.0049)y - 0.9804(0.0089)z = 7.0274(0.0041)

Angle to previous plane (with approximate e.s.d.) = 79.23 (5)

* 0.0038(0.0011) C11 * -0.0050(0.0012) C12 * 0.0019(0.0013) C13 * 0.0023(0.0013) C14 * -0.0034(0.0014) C15 * 0.0003(0.0012) C16 - 0.9213(0.0027) O1 1.0898(0.0035) N3 - 3.0060(0.0065) O31

Rms deviation of fitted atoms = 0.0031

5.4276(0.0049)x + 5.5914(0.0040)y + 5.0163(0.0064)z = 5.3766(0.0019)

Angle to previous plane (with approximate e.s.d.) = 33.58 (7)

* -0.0039(0.0010) C21 * 0.0037(0.0011) C22 * 0.0004(0.0011) C23 * -0.0042(0.0011) C24 * 0.0040(0.0012) C25 * 0.0001(0.0012) C26 - 0.0367(0.0024) C2 1.0033(0.0027) N3 - 0.0242(0.0022) O31

Rms deviation of fitted atoms = 0.0032

6.3817(0.0053)x - 4.9149(0.0065)y + 4.6448(0.0094)z = 2.0603(0.0054)

Angle to previous plane (with approximate e.s.d.)= 79.14 (5)

* 0.0677(0.0009) O1 * -0.0432(0.0005) C2 * 0.0392(0.0005) C4 * -0.0637(0.0008) C5 0.3018(0.0035) C31 0.8534(0.0031) C41 0.9774(0.0027) C11 0.6124(0.0026) C21 0.6017(0.0021) N3 2.4693(0.0051) O31

Rms deviation of fitted atoms = 0.0549

6.2495(0.0113)x + 4.9688(0.0152)y + 4.8026(0.0106)z = 5.5802(0.0070)

Angle to previous plane (with approximate e.s.d.) = 73.35 (10)

* 0.0406 (0.0009) O31 * -0.0373 (0.0008) C32 * -0.0429 (0.0009) C33 * 0.0396 (0.0009) C34 0.0867 (0.0057) C21 0.0603 (0.0027) C24 0.0663 (0.0074) C2 - 1.0601 (0.0070) O1

Rms deviation of fitted atoms = 0.0401

5.4276(0.0049)x + 5.5914(0.0040)y + 5.0163(0.0064)z = 5.3766(0.0019)

Angle to previous plane (with approximate e.s.d.) = 6.7 (2)

* -0.0039 (0.0010) C21 * 0.0037 (0.0011) C22 * 0.0004 (0.0011) C23 * -0.0042 (0.0011) C24 * 0.0040 (0.0012) C25 * 0.0001 (0.0012) C26 - 0.0242 (0.0022) O31 - 1.2464 (0.0025) O1

Rms deviation of fitted atoms = 0.0032

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
O10.62951 (11)0.25267 (14)0.13941 (9)0.0336 (3)
C20.64463 (15)0.37668 (18)0.05284 (12)0.0284 (3)
N30.79419 (13)0.42830 (16)0.06489 (10)0.0298 (3)
C310.82173 (18)0.5817 (2)0.00494 (14)0.0400 (4)
C40.80871 (16)0.4413 (2)0.19220 (13)0.0319 (3)
C410.96437 (19)0.4422 (2)0.22974 (17)0.0447 (4)
C50.71528 (16)0.2981 (2)0.23745 (13)0.0316 (3)
C110.79682 (16)0.15241 (19)0.27952 (13)0.0335 (3)
C120.86946 (17)0.0513 (2)0.20172 (15)0.0384 (4)
C130.9480 (2)0.0799 (2)0.2413 (2)0.0504 (5)
C140.9534 (2)0.1127 (3)0.3595 (2)0.0595 (6)
C150.8799 (2)0.0135 (3)0.43796 (19)0.0602 (6)
C160.80236 (19)0.1184 (3)0.39881 (14)0.0456 (4)
C210.60989 (15)0.31007 (18)0.06553 (12)0.0282 (3)
C220.49376 (16)0.36969 (19)0.12624 (13)0.0296 (3)
C230.45726 (15)0.30686 (19)0.23513 (13)0.0298 (3)
C240.53876 (15)0.1832 (2)0.28387 (12)0.0287 (3)
C250.65725 (16)0.1231 (2)0.22425 (13)0.0345 (3)
C260.69145 (15)0.1862 (2)0.11617 (13)0.0337 (3)
O310.51184 (12)0.11104 (15)0.38943 (9)0.0361 (3)
C320.39621 (16)0.1753 (2)0.45720 (13)0.0327 (3)
C330.38810 (17)0.0773 (2)0.56802 (14)0.0377 (4)
C340.2810 (2)0.1468 (3)0.65260 (16)0.0527 (5)
H20.57850.46850.07240.034*
H31A0.75560.66420.03580.060*
H31B0.92120.61550.01800.060*
H31C0.80680.56820.07920.060*
H40.76250.54440.21870.038*
H41A1.01100.54200.20270.067*
H41B0.96810.43640.31530.067*
H41C1.01460.34890.19550.067*
H50.65030.33740.30210.038*
H120.86550.07220.12010.046*
H130.99800.14720.18690.060*
H141.00700.20250.38680.071*
H150.88280.03610.51940.072*
H160.75280.18570.45350.055*
H220.43790.45490.09320.036*
H230.37700.34870.27550.036*
H250.71420.03920.25790.041*
H260.77180.14440.07580.040*
H32A0.30430.16790.41240.039*
H32B0.41460.29030.47610.039*
H33A0.48440.07370.60640.045*
H33B0.35990.03490.54810.045*
H34A0.31240.25490.67710.079*
H34B0.27520.07660.72140.079*
H34C0.18610.15400.61410.079*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0342 (5)0.0392 (6)0.0276 (5)0.0073 (5)0.0087 (4)0.0026 (5)
C20.0276 (6)0.0318 (7)0.0257 (7)0.0008 (6)0.0025 (5)0.0023 (6)
N30.0290 (6)0.0338 (7)0.0268 (6)0.0023 (5)0.0028 (5)0.0027 (5)
C310.0463 (9)0.0408 (9)0.0331 (8)0.0092 (7)0.0018 (7)0.0012 (7)
C40.0358 (7)0.0310 (7)0.0292 (7)0.0008 (6)0.0073 (6)0.0037 (6)
C410.0424 (9)0.0413 (9)0.0510 (10)0.0111 (8)0.0192 (8)0.0065 (8)
C50.0314 (7)0.0395 (8)0.0241 (7)0.0035 (6)0.0043 (5)0.0033 (6)
C110.0324 (7)0.0373 (9)0.0311 (7)0.0081 (6)0.0059 (6)0.0042 (6)
C120.0386 (8)0.0368 (9)0.0401 (9)0.0036 (7)0.0038 (7)0.0027 (7)
C130.0457 (10)0.0361 (9)0.0697 (13)0.0018 (8)0.0117 (9)0.0029 (9)
C140.0542 (11)0.0425 (11)0.0827 (16)0.0081 (9)0.0286 (11)0.0218 (11)
C150.0653 (13)0.0657 (14)0.0504 (12)0.0212 (11)0.0265 (10)0.0249 (10)
C160.0475 (9)0.0580 (11)0.0317 (8)0.0128 (8)0.0098 (7)0.0074 (8)
C210.0276 (6)0.0299 (7)0.0270 (7)0.0008 (6)0.0014 (5)0.0018 (6)
C220.0307 (7)0.0297 (7)0.0284 (7)0.0027 (6)0.0027 (5)0.0031 (6)
C230.0301 (7)0.0324 (7)0.0272 (7)0.0026 (6)0.0061 (6)0.0000 (6)
C240.0298 (7)0.0327 (7)0.0237 (6)0.0003 (6)0.0034 (5)0.0024 (6)
C250.0316 (7)0.0398 (9)0.0322 (8)0.0093 (6)0.0050 (6)0.0083 (7)
C260.0294 (7)0.0402 (8)0.0319 (7)0.0067 (6)0.0079 (6)0.0061 (7)
O310.0386 (6)0.0433 (7)0.0266 (5)0.0094 (5)0.0106 (4)0.0098 (5)
C320.0336 (7)0.0370 (8)0.0279 (7)0.0021 (6)0.0083 (6)0.0005 (6)
C330.0397 (8)0.0431 (9)0.0307 (8)0.0020 (7)0.0080 (6)0.0063 (7)
C340.0626 (11)0.0601 (12)0.0362 (9)0.0003 (10)0.0211 (8)0.0056 (8)
Geometric parameters (Å, º) top
O1—C21.4305 (18)C2—H21.000
O1—C51.4373 (17)C31—H31A0.980
C2—N31.4635 (18)C31—H31B0.980
C2—C211.5014 (19)C31—H31C0.980
N3—C311.463 (2)C4—H41.000
N3—C41.4676 (18)C41—H41A0.980
C4—C411.517 (2)C41—H41B0.980
C4—C51.552 (2)C41—H41C0.980
C5—C111.508 (2)C5—H51.000
C11—C121.387 (2)C12—H120.950
C11—C161.394 (2)C13—H130.950
C12—C131.389 (3)C14—H140.950
C13—C141.379 (3)C15—H150.950
C14—C151.386 (3)C16—H160.950
C15—C161.387 (3)C22—H220.950
C21—C221.385 (2)C23—H230.950
C21—C261.394 (2)C25—H250.950
C22—C231.396 (2)C26—H260.950
C23—C241.384 (2)C32—H32A0.990
C24—O311.3731 (17)C32—H32B0.990
C24—C251.398 (2)C33—H33A0.990
C25—C261.383 (2)C33—H33B0.990
O31—C321.4386 (17)C34—H34A0.980
C32—C331.507 (2)C34—H34B0.980
C33—C341.514 (2)C34—H34C0.980
C2—O1—C5107.60 (11)C5—C4—H4108.4
O1—C2—N3103.03 (11)C4—C41—H41A109.5
O1—C2—C21109.85 (12)C4—C41—H41B109.5
N3—C2—C21114.38 (12)H41A—C41—H41B109.5
C31—N3—C2111.56 (12)C4—C41—H41C109.5
C31—N3—C4112.46 (12)H41A—C41—H41C109.5
C2—N3—C4102.71 (11)H41B—C41—H41C109.5
N3—C4—C41112.76 (13)O1—C5—H5108.9
N3—C4—C5102.30 (11)C11—C5—H5108.9
C41—C4—C5116.15 (14)C4—C5—H5108.9
O1—C5—C11109.19 (12)C11—C12—H12119.5
O1—C5—C4104.80 (12)C13—C12—H12119.5
C11—C5—C4115.79 (12)C14—C13—H13119.9
C12—C11—C16118.58 (16)C12—C13—H13119.9
C12—C11—C5121.31 (14)C13—C14—H14120.3
C16—C11—C5120.10 (15)C15—C14—H14120.3
C11—C12—C13121.01 (17)C14—C15—H15119.7
C14—C13—C12120.1 (2)C16—C15—H15119.7
C13—C14—C15119.34 (19)C15—C16—H16119.9
C14—C15—C16120.68 (19)C11—C16—H16119.9
C15—C16—C11120.2 (2)C21—C22—H22119.4
C22—C21—C26118.49 (13)C23—C22—H22119.4
C22—C21—C2120.22 (13)C24—C23—H23120.2
C26—C21—C2121.28 (13)C22—C23—H23120.2
C21—C22—C23121.23 (14)C26—C25—H25120.1
C24—C23—C22119.58 (13)C24—C25—H25120.1
O31—C24—C23124.58 (13)C25—C26—H26119.5
O31—C24—C25115.60 (13)C21—C26—H26119.5
C23—C24—C25119.82 (13)O31—C32—H32A110.2
C26—C25—C24119.85 (14)C33—C32—H32A110.2
C25—C26—C21121.03 (14)O31—C32—H32B110.2
C24—O31—C32117.55 (12)C33—C32—H32B110.2
O31—C32—C33107.64 (13)H32A—C32—H32B108.5
C32—C33—C34112.06 (15)C32—C33—H33A109.2
O1—C2—H2109.8C34—C33—H33A109.2
N3—C2—H2109.8C32—C33—H33B109.2
C21—C2—H2109.8C34—C33—H33B109.2
N3—C31—H31A109.5H33A—C33—H33B107.9
N3—C31—H31B109.5C33—C34—H34A109.5
H31A—C31—H31B109.5C33—C34—H34B109.5
N3—C31—H31C109.5H34A—C34—H34B109.5
H31A—C31—H31C109.5C33—C34—H34C109.5
H31B—C31—H31C109.5H34A—C34—H34C109.5
N3—C4—H4108.4H34B—C34—H34C109.5
C41—C4—H4108.4
C5—O1—C2—N335.09 (14)C12—C13—C14—C150.0 (3)
C5—O1—C2—C21157.36 (12)C13—C14—C15—C160.5 (3)
O1—C2—N3—C31165.60 (11)C14—C15—C16—C110.3 (3)
C21—C2—N3—C3175.22 (16)C12—C11—C16—C150.4 (2)
O1—C2—N3—C444.92 (14)C5—C11—C16—C15178.55 (16)
C21—C2—N3—C4164.10 (13)O1—C2—C21—C22116.58 (15)
C31—N3—C4—C4177.85 (18)N3—C2—C21—C22128.16 (15)
C2—N3—C4—C41162.09 (14)O1—C2—C21—C2662.48 (17)
C31—N3—C4—C5156.66 (12)N3—C2—C21—C2652.78 (19)
C2—N3—C4—C536.61 (14)C26—C21—C22—C230.7 (2)
C2—O1—C5—C11136.36 (12)C2—C21—C22—C23178.39 (14)
C2—O1—C5—C411.71 (15)C21—C22—C23—C240.3 (2)
N3—C4—C5—O115.80 (15)C22—C23—C24—O31179.17 (14)
C41—C4—C5—O1139.03 (14)C22—C23—C24—C250.5 (2)
N3—C4—C5—C11104.55 (14)O31—C24—C25—C26178.86 (15)
C41—C4—C5—C1118.68 (19)C23—C24—C25—C260.8 (2)
O1—C5—C11—C1246.28 (18)C24—C25—C26—C210.4 (3)
C4—C5—C11—C1271.67 (18)C22—C21—C26—C250.4 (2)
O1—C5—C11—C16134.80 (14)C2—C21—C26—C25178.72 (15)
C4—C5—C11—C16107.25 (16)C23—C24—O31—C324.0 (2)
C16—C11—C12—C130.9 (2)C25—C24—O31—C32176.37 (14)
C5—C11—C12—C13178.03 (15)C24—O31—C32—C33179.93 (13)
C11—C12—C13—C140.7 (3)O31—C32—C33—C34173.36 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22···O1i0.952.603.3745 (19)139
C23—H23···Cg1i0.952.793.6987 (16)161
Symmetry code: (i) x+1, y+1/2, z.
 

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