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The absolute configuration of the title compound, C24H23NO2, has been confirmed as 3R,4R. The hydroxy­methyl group and phenyl ring at the asymmetric C atoms exhibit α and β orientations, respectively, and the non-planar heterocyclic ring of the tetra­hydro­isoquinoline system adopts an envelope conformation. The crystal structure is stabilized through hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806012189/tk2023sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806012189/tk2023Isup2.hkl
Contains datablock I

CCDC reference: 608509

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.029
  • wR factor = 0.087
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.20
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 70.10 From the CIF: _reflns_number_total 3480 Count of symmetry unique reflns 2075 Completeness (_total/calc) 167.71% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1405 Fraction of Friedel pairs measured 0.677 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: KM-4 Software (Kuma, 1996); cell refinement: KM-4 Software; data reduction: KM-4 Software; 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: WinGX (Farrugia, 1999).

(3R,4R)-(-)-3-Hydroxymethyl-4-phenyl-2-o-toluoyl-1,2,3,4-tetrahydroisoquinoline top
Crystal data top
C24H23NO2Dx = 1.249 Mg m3
Mr = 357.43Melting point = 458–462 K
Orthorhombic, P212121Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2abCell parameters from 58 reflections
a = 9.0424 (10) Åθ = 14.7–29.1°
b = 10.4114 (11) ŵ = 0.62 mm1
c = 20.191 (2) ÅT = 293 K
V = 1900.9 (3) Å3Block, colourless
Z = 40.40 × 0.20 × 0.15 mm
F(000) = 760
Data collection top
Kuma KM-4
diffractometer
Rint = 0.013
Radiation source: fine-focus sealed tubeθmax = 70.1°, θmin = 4.4°
Graphite monochromatorh = 1111
ω/2θ scansk = 012
3740 measured reflectionsl = 024
3480 independent reflections2 standard reflections every 100 reflections
3297 reflections with I > 2σ(I) intensity decay: <2%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.029 w = 1/[σ2(Fo2) + (0.0537P)2 + 0.1426P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.087(Δ/σ)max = 0.001
S = 1.07Δρmax = 0.13 e Å3
3480 reflectionsΔρmin = 0.09 e Å3
250 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0036 (4)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), with how many Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.0 (2)
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
C10.44091 (19)0.83719 (13)0.11613 (8)0.0544 (4)
H1A0.50040.76690.13290.065*
H1B0.35100.80080.09780.065*
N20.52246 (12)0.90153 (10)0.06302 (5)0.0403 (2)
C30.49068 (14)1.03822 (11)0.05355 (6)0.0381 (3)
H30.55441.07080.01810.046*
C40.52938 (13)1.10955 (12)0.11789 (6)0.0391 (3)
H40.49761.19890.11250.047*
C50.40131 (15)1.12892 (15)0.22788 (7)0.0509 (3)
H50.43001.21470.22910.061*
C60.31886 (18)1.07900 (18)0.27948 (8)0.0607 (4)
H60.29281.13060.31520.073*
C70.27576 (18)0.9527 (2)0.27748 (8)0.0628 (4)
H70.21920.91880.31180.075*
C80.31584 (17)0.87600 (15)0.22498 (8)0.0556 (4)
H80.28590.79060.22420.067*
C90.40056 (15)0.92433 (13)0.17301 (7)0.0448 (3)
C100.44190 (14)1.05321 (13)0.17442 (6)0.0415 (3)
C110.61862 (15)0.83351 (12)0.02637 (7)0.0444 (3)
O120.64271 (14)0.71940 (10)0.03810 (7)0.0694 (3)
C130.69725 (15)0.90063 (13)0.02888 (7)0.0459 (3)
C140.64575 (19)0.89127 (15)0.09363 (8)0.0582 (4)
C150.7243 (3)0.95566 (19)0.14280 (9)0.0748 (5)
H150.68950.95410.18610.090*
C160.8521 (3)1.02133 (19)0.12863 (11)0.0795 (6)
H160.90291.06280.16250.095*
C170.9059 (2)1.02653 (17)0.06503 (11)0.0715 (5)
H170.99351.06980.05580.086*
C180.82795 (17)0.96670 (14)0.01513 (8)0.0545 (3)
H180.86280.97040.02820.065*
C190.5136 (2)0.8105 (2)0.11049 (12)0.0873 (6)
H19A0.54210.72180.11230.131*
H19B0.47510.83630.15280.131*
H19C0.43880.82180.07720.131*
C200.32977 (15)1.06018 (14)0.03368 (7)0.0486 (3)
H20A0.26561.01890.06580.058*
H20B0.30891.15150.03450.058*
O210.29829 (13)1.01154 (10)0.02983 (5)0.0565 (3)
H210.252 (2)0.936 (2)0.0248 (10)0.072 (6)*
C220.69512 (14)1.11086 (12)0.13077 (6)0.0415 (3)
C230.77994 (17)1.20927 (15)0.10436 (8)0.0541 (3)
H230.73511.27310.07920.065*
C240.93128 (19)1.2131 (2)0.11528 (11)0.0724 (5)
H240.98731.27970.09760.087*
C250.99895 (18)1.1188 (2)0.15213 (10)0.0771 (6)
H251.10051.12170.15940.092*
C260.91606 (19)1.0203 (2)0.17825 (9)0.0698 (5)
H260.96170.95630.20300.084*
C270.76452 (17)1.01635 (16)0.16772 (7)0.0543 (3)
H270.70900.94960.18560.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0642 (9)0.0388 (7)0.0601 (9)0.0047 (6)0.0136 (7)0.0059 (6)
N20.0432 (6)0.0334 (5)0.0443 (5)0.0020 (4)0.0020 (5)0.0024 (4)
C30.0385 (6)0.0338 (6)0.0421 (6)0.0013 (5)0.0003 (5)0.0042 (5)
C40.0390 (6)0.0343 (5)0.0441 (6)0.0012 (5)0.0018 (5)0.0018 (5)
C50.0433 (7)0.0609 (8)0.0485 (7)0.0021 (6)0.0033 (6)0.0054 (6)
C60.0500 (8)0.0837 (11)0.0485 (8)0.0001 (8)0.0102 (7)0.0046 (7)
C70.0500 (8)0.0898 (12)0.0486 (8)0.0018 (8)0.0104 (7)0.0151 (8)
C80.0505 (8)0.0584 (8)0.0579 (8)0.0034 (7)0.0036 (7)0.0164 (7)
C90.0409 (6)0.0466 (6)0.0469 (7)0.0009 (5)0.0009 (6)0.0089 (5)
C100.0346 (6)0.0467 (7)0.0432 (7)0.0019 (5)0.0009 (5)0.0033 (5)
C110.0425 (7)0.0375 (6)0.0533 (7)0.0016 (5)0.0004 (6)0.0025 (5)
O120.0778 (8)0.0394 (5)0.0909 (8)0.0134 (5)0.0217 (7)0.0052 (5)
C130.0449 (7)0.0424 (6)0.0503 (7)0.0070 (5)0.0051 (6)0.0042 (5)
C140.0604 (9)0.0601 (9)0.0540 (8)0.0148 (7)0.0006 (7)0.0045 (7)
C150.0946 (15)0.0756 (11)0.0541 (9)0.0265 (11)0.0084 (9)0.0073 (8)
C160.0896 (14)0.0669 (10)0.0820 (13)0.0125 (10)0.0320 (11)0.0186 (9)
C170.0598 (9)0.0578 (9)0.0968 (14)0.0024 (8)0.0202 (10)0.0033 (9)
C180.0487 (8)0.0494 (7)0.0654 (9)0.0009 (6)0.0073 (7)0.0050 (6)
C190.0717 (12)0.1122 (17)0.0781 (13)0.0028 (12)0.0171 (11)0.0237 (12)
C200.0444 (7)0.0488 (7)0.0527 (7)0.0053 (6)0.0059 (6)0.0007 (6)
O210.0634 (6)0.0509 (5)0.0553 (6)0.0100 (5)0.0163 (5)0.0044 (4)
C220.0393 (6)0.0452 (6)0.0400 (6)0.0013 (5)0.0025 (5)0.0067 (5)
C230.0500 (8)0.0541 (8)0.0583 (8)0.0074 (6)0.0075 (7)0.0035 (7)
C240.0496 (9)0.0856 (12)0.0820 (12)0.0234 (9)0.0132 (8)0.0162 (10)
C250.0378 (8)0.1195 (17)0.0739 (12)0.0052 (10)0.0014 (8)0.0299 (11)
C260.0503 (8)0.1013 (14)0.0579 (9)0.0167 (9)0.0090 (7)0.0056 (9)
C270.0480 (7)0.0643 (9)0.0506 (7)0.0043 (7)0.0024 (6)0.0029 (7)
Geometric parameters (Å, º) top
C1—N21.4638 (17)C14—C191.501 (3)
C1—C91.508 (2)C15—C161.373 (3)
C1—H1A0.9700C15—H150.9300
C1—H1B0.9700C16—C171.374 (3)
N2—C111.3436 (16)C16—H160.9300
N2—C31.4644 (15)C17—C181.378 (2)
C3—C201.5265 (18)C17—H170.9300
C3—C41.5368 (18)C18—H180.9300
C3—H30.9800C19—H19A0.9600
C4—C101.5077 (17)C19—H19B0.9600
C4—C221.5211 (17)C19—H19C0.9600
C4—H40.9800C20—O211.4079 (18)
C5—C61.383 (2)C20—H20A0.9700
C5—C101.3860 (19)C20—H20B0.9700
C5—H50.9300O21—H210.90 (2)
C6—C71.372 (3)C22—C271.385 (2)
C6—H60.9300C22—C231.387 (2)
C7—C81.376 (3)C23—C241.387 (2)
C7—H70.9300C23—H230.9300
C8—C91.393 (2)C24—C251.375 (3)
C8—H80.9300C24—H240.9300
C9—C101.3932 (19)C25—C261.375 (3)
C11—O121.2309 (16)C25—H250.9300
C11—C131.4960 (19)C26—C271.387 (2)
C13—C141.391 (2)C26—H260.9300
C13—C181.395 (2)C27—H270.9300
C14—C151.393 (3)
N2—C1—C9113.86 (11)C13—C14—C19121.26 (16)
N2—C1—H1A108.8C15—C14—C19120.96 (17)
C9—C1—H1A108.8C16—C15—C14121.37 (17)
N2—C1—H1B108.8C16—C15—H15119.3
C9—C1—H1B108.8C14—C15—H15119.3
H1A—C1—H1B107.7C15—C16—C17120.81 (17)
C11—N2—C1119.23 (11)C15—C16—H16119.6
C11—N2—C3124.56 (10)C17—C16—H16119.6
C1—N2—C3116.20 (10)C16—C17—C18118.98 (18)
N2—C3—C20111.52 (10)C16—C17—H17120.5
N2—C3—C4108.33 (10)C18—C17—H17120.5
C20—C3—C4111.52 (11)C17—C18—C13120.68 (16)
N2—C3—H3108.5C17—C18—H18119.7
C20—C3—H3108.5C13—C18—H18119.7
C4—C3—H3108.5C14—C19—H19A109.5
C10—C4—C22113.01 (10)C14—C19—H19B109.5
C10—C4—C3109.42 (10)H19A—C19—H19B109.5
C22—C4—C3111.92 (10)C14—C19—H19C109.5
C10—C4—H4107.4H19A—C19—H19C109.5
C22—C4—H4107.4H19B—C19—H19C109.5
C3—C4—H4107.4O21—C20—C3112.22 (12)
C6—C5—C10121.05 (14)O21—C20—H20A109.2
C6—C5—H5119.5C3—C20—H20A109.2
C10—C5—H5119.5O21—C20—H20B109.2
C7—C6—C5119.42 (15)C3—C20—H20B109.2
C7—C6—H6120.3H20A—C20—H20B107.9
C5—C6—H6120.3C20—O21—H21107.8 (13)
C6—C7—C8120.27 (14)C27—C22—C23118.78 (13)
C6—C7—H7119.9C27—C22—C4122.15 (13)
C8—C7—H7119.9C23—C22—C4119.07 (13)
C7—C8—C9121.03 (15)C22—C23—C24120.39 (17)
C7—C8—H8119.5C22—C23—H23119.8
C9—C8—H8119.5C24—C23—H23119.8
C8—C9—C10118.69 (14)C25—C24—C23120.32 (17)
C8—C9—C1119.29 (13)C25—C24—H24119.8
C10—C9—C1122.00 (12)C23—C24—H24119.8
C5—C10—C9119.51 (12)C24—C25—C26119.80 (15)
C5—C10—C4120.48 (12)C24—C25—H25120.1
C9—C10—C4120.00 (12)C26—C25—H25120.1
O12—C11—N2121.15 (13)C25—C26—C27120.13 (19)
O12—C11—C13120.68 (12)C25—C26—H26119.9
N2—C11—C13118.17 (10)C27—C26—H26119.9
C14—C13—C18120.33 (14)C22—C27—C26120.58 (17)
C14—C13—C11120.59 (13)C22—C27—H27119.7
C18—C13—C11118.98 (12)C26—C27—H27119.7
C13—C14—C15117.73 (16)
C9—C1—N2—C11150.62 (12)C3—N2—C11—C131.16 (19)
C9—C1—N2—C329.93 (18)O12—C11—C13—C1483.25 (18)
C11—N2—C3—C20116.59 (14)N2—C11—C13—C1497.40 (16)
C1—N2—C3—C2062.83 (15)O12—C11—C13—C1893.08 (17)
C11—N2—C3—C4120.31 (13)N2—C11—C13—C1886.28 (16)
C1—N2—C3—C460.27 (15)C18—C13—C14—C153.5 (2)
N2—C3—C4—C1057.68 (13)C11—C13—C14—C15179.76 (13)
C20—C3—C4—C1065.42 (13)C18—C13—C14—C19174.19 (15)
N2—C3—C4—C2268.38 (13)C11—C13—C14—C192.1 (2)
C20—C3—C4—C22168.52 (11)C13—C14—C15—C163.0 (2)
C10—C5—C6—C70.4 (2)C19—C14—C15—C16174.72 (18)
C5—C6—C7—C80.8 (2)C14—C15—C16—C170.6 (3)
C6—C7—C8—C90.0 (2)C15—C16—C17—C181.2 (3)
C7—C8—C9—C101.3 (2)C16—C17—C18—C130.7 (2)
C7—C8—C9—C1179.47 (14)C14—C13—C18—C171.7 (2)
N2—C1—C9—C8176.57 (13)C11—C13—C18—C17178.08 (13)
N2—C1—C9—C101.6 (2)N2—C3—C20—O2167.49 (14)
C6—C5—C10—C90.8 (2)C4—C3—C20—O21171.24 (10)
C6—C5—C10—C4178.85 (13)C10—C4—C22—C2732.87 (17)
C8—C9—C10—C51.6 (2)C3—C4—C22—C2791.20 (14)
C1—C9—C10—C5179.78 (13)C10—C4—C22—C23147.57 (13)
C8—C9—C10—C4178.03 (12)C3—C4—C22—C2388.35 (15)
C1—C9—C10—C40.13 (19)C27—C22—C23—C240.5 (2)
C22—C4—C10—C584.52 (15)C4—C22—C23—C24179.97 (14)
C3—C4—C10—C5150.04 (12)C22—C23—C24—C250.4 (3)
C22—C4—C10—C995.83 (14)C23—C24—C25—C260.0 (3)
C3—C4—C10—C929.60 (15)C24—C25—C26—C270.3 (3)
C1—N2—C11—O122.4 (2)C23—C22—C27—C260.2 (2)
C3—N2—C11—O12178.19 (13)C4—C22—C27—C26179.74 (14)
C1—N2—C11—C13178.25 (13)C25—C26—C27—C220.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O21—H21···O12i0.90 (2)1.91 (2)2.7907 (16)165.0 (19)
C19—H19C···O210.962.543.290 (2)135
C23—H23···O21ii0.932.523.2774 (19)139
Symmetry codes: (i) x1/2, y+3/2, z; (ii) x+1/2, y+5/2, z.
 

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