(3R,4R)-(–)-3-Hydroxy­methyl-4-phenyl-2-o-toluoyl-1,2,3,4-tetra­hydro­isoquinoline

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.

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

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Computing details

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

Crystal data

C24H23NO2	Dx = 1.249 Mg m^−3
Mr = 357.43	Melting point = 458–462 K
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 58 reflections
a = 9.0424 (10) Å	θ = 14.7–29.1°
b = 10.4114 (11) Å	µ = 0.62 mm^−1
c = 20.191 (2) Å	T = 293 K
V = 1900.9 (3) Å^3	Block, colourless
Z = 4	0.40 × 0.20 × 0.15 mm
F(000) = 760

Data collection

Kuma KM-4 diffractometer	Rint = 0.013
Radiation source: fine-focus sealed tube	θmax = 70.1°, θmin = 4.4°
Graphite monochromator	h = −11→11
ω/2θ scans	k = 0→12
3740 measured reflections	l = 0→24
3480 independent reflections	2 standard reflections every 100 reflections
3297 reflections with I > 2σ(I)	intensity decay: <2%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.029	w = 1/[σ^2(Fo^2) + (0.0537P)^2 + 0.1426P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.087	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.13 e Å^−3
3480 reflections	Δρmin = −0.09 e Å^−3
250 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0036 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with how many Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.0 (2)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.44091 (19)	0.83719 (13)	0.11613 (8)	0.0544 (4)
H1A	0.5004	0.7669	0.1329	0.065*
H1B	0.3510	0.8008	0.0978	0.065*
N2	0.52246 (12)	0.90153 (10)	0.06302 (5)	0.0403 (2)
C3	0.49068 (14)	1.03822 (11)	0.05355 (6)	0.0381 (3)
H3	0.5544	1.0708	0.0181	0.046*
C4	0.52938 (13)	1.10955 (12)	0.11789 (6)	0.0391 (3)
H4	0.4976	1.1989	0.1125	0.047*
C5	0.40131 (15)	1.12892 (15)	0.22788 (7)	0.0509 (3)
H5	0.4300	1.2147	0.2291	0.061*
C6	0.31886 (18)	1.07900 (18)	0.27948 (8)	0.0607 (4)
H6	0.2928	1.1306	0.3152	0.073*
C7	0.27576 (18)	0.9527 (2)	0.27748 (8)	0.0628 (4)
H7	0.2192	0.9188	0.3118	0.075*
C8	0.31584 (17)	0.87600 (15)	0.22498 (8)	0.0556 (4)
H8	0.2859	0.7906	0.2242	0.067*
C9	0.40056 (15)	0.92433 (13)	0.17301 (7)	0.0448 (3)
C10	0.44190 (14)	1.05321 (13)	0.17442 (6)	0.0415 (3)
C11	0.61862 (15)	0.83351 (12)	0.02637 (7)	0.0444 (3)
O12	0.64271 (14)	0.71940 (10)	0.03810 (7)	0.0694 (3)
C13	0.69725 (15)	0.90063 (13)	−0.02888 (7)	0.0459 (3)
C14	0.64575 (19)	0.89127 (15)	−0.09363 (8)	0.0582 (4)
C15	0.7243 (3)	0.95566 (19)	−0.14280 (9)	0.0748 (5)
H15	0.6895	0.9541	−0.1861	0.090*
C16	0.8521 (3)	1.02133 (19)	−0.12863 (11)	0.0795 (6)
H16	0.9029	1.0628	−0.1625	0.095*
C17	0.9059 (2)	1.02653 (17)	−0.06503 (11)	0.0715 (5)
H17	0.9935	1.0698	−0.0558	0.086*
C18	0.82795 (17)	0.96670 (14)	−0.01513 (8)	0.0545 (3)
H18	0.8628	0.9704	0.0282	0.065*
C19	0.5136 (2)	0.8105 (2)	−0.11049 (12)	0.0873 (6)
H19A	0.5421	0.7218	−0.1123	0.131*
H19B	0.4751	0.8363	−0.1528	0.131*
H19C	0.4388	0.8218	−0.0772	0.131*
C20	0.32977 (15)	1.06018 (14)	0.03368 (7)	0.0486 (3)
H20A	0.2656	1.0189	0.0658	0.058*
H20B	0.3089	1.1515	0.0345	0.058*
O21	0.29829 (13)	1.01154 (10)	−0.02983 (5)	0.0565 (3)
H21	0.252 (2)	0.936 (2)	−0.0248 (10)	0.072 (6)*
C22	0.69512 (14)	1.11086 (12)	0.13077 (6)	0.0415 (3)
C23	0.77994 (17)	1.20927 (15)	0.10436 (8)	0.0541 (3)
H23	0.7351	1.2731	0.0792	0.065*
C24	0.93128 (19)	1.2131 (2)	0.11528 (11)	0.0724 (5)
H24	0.9873	1.2797	0.0976	0.087*
C25	0.99895 (18)	1.1188 (2)	0.15213 (10)	0.0771 (6)
H25	1.1005	1.1217	0.1594	0.092*
C26	0.91606 (19)	1.0203 (2)	0.17825 (9)	0.0698 (5)
H26	0.9617	0.9563	0.2030	0.084*
C27	0.76452 (17)	1.01635 (16)	0.16772 (7)	0.0543 (3)
H27	0.7090	0.9496	0.1856	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0642 (9)	0.0388 (7)	0.0601 (9)	−0.0047 (6)	0.0136 (7)	0.0059 (6)
N2	0.0432 (6)	0.0334 (5)	0.0443 (5)	0.0020 (4)	0.0020 (5)	0.0024 (4)
C3	0.0385 (6)	0.0338 (6)	0.0421 (6)	0.0013 (5)	0.0003 (5)	0.0042 (5)
C4	0.0390 (6)	0.0343 (5)	0.0441 (6)	0.0012 (5)	0.0018 (5)	0.0018 (5)
C5	0.0433 (7)	0.0609 (8)	0.0485 (7)	−0.0021 (6)	0.0033 (6)	−0.0054 (6)
C6	0.0500 (8)	0.0837 (11)	0.0485 (8)	0.0001 (8)	0.0102 (7)	−0.0046 (7)
C7	0.0500 (8)	0.0898 (12)	0.0486 (8)	−0.0018 (8)	0.0104 (7)	0.0151 (8)
C8	0.0505 (8)	0.0584 (8)	0.0579 (8)	−0.0034 (7)	0.0036 (7)	0.0164 (7)
C9	0.0409 (6)	0.0466 (6)	0.0469 (7)	0.0009 (5)	0.0009 (6)	0.0089 (5)
C10	0.0346 (6)	0.0467 (7)	0.0432 (7)	0.0019 (5)	0.0009 (5)	0.0033 (5)
C11	0.0425 (7)	0.0375 (6)	0.0533 (7)	0.0016 (5)	−0.0004 (6)	−0.0025 (5)
O12	0.0778 (8)	0.0394 (5)	0.0909 (8)	0.0134 (5)	0.0217 (7)	0.0052 (5)
C13	0.0449 (7)	0.0424 (6)	0.0503 (7)	0.0070 (5)	0.0051 (6)	−0.0042 (5)
C14	0.0604 (9)	0.0601 (9)	0.0540 (8)	0.0148 (7)	−0.0006 (7)	−0.0045 (7)
C15	0.0946 (15)	0.0756 (11)	0.0541 (9)	0.0265 (11)	0.0084 (9)	0.0073 (8)
C16	0.0896 (14)	0.0669 (10)	0.0820 (13)	0.0125 (10)	0.0320 (11)	0.0186 (9)
C17	0.0598 (9)	0.0578 (9)	0.0968 (14)	−0.0024 (8)	0.0202 (10)	0.0033 (9)
C18	0.0487 (8)	0.0494 (7)	0.0654 (9)	0.0009 (6)	0.0073 (7)	−0.0050 (6)
C19	0.0717 (12)	0.1122 (17)	0.0781 (13)	0.0028 (12)	−0.0171 (11)	−0.0237 (12)
C20	0.0444 (7)	0.0488 (7)	0.0527 (7)	0.0053 (6)	−0.0059 (6)	0.0007 (6)
O21	0.0634 (6)	0.0509 (5)	0.0553 (6)	−0.0100 (5)	−0.0163 (5)	0.0044 (4)
C22	0.0393 (6)	0.0452 (6)	0.0400 (6)	−0.0013 (5)	0.0025 (5)	−0.0067 (5)
C23	0.0500 (8)	0.0541 (8)	0.0583 (8)	−0.0074 (6)	0.0075 (7)	−0.0035 (7)
C24	0.0496 (9)	0.0856 (12)	0.0820 (12)	−0.0234 (9)	0.0132 (8)	−0.0162 (10)
C25	0.0378 (8)	0.1195 (17)	0.0739 (12)	−0.0052 (10)	0.0014 (8)	−0.0299 (11)
C26	0.0503 (8)	0.1013 (14)	0.0579 (9)	0.0167 (9)	−0.0090 (7)	−0.0056 (9)
C27	0.0480 (7)	0.0643 (9)	0.0506 (7)	0.0043 (7)	−0.0024 (6)	0.0029 (7)

Geometric parameters (Å, º)

C1—N2	1.4638 (17)	C14—C19	1.501 (3)
C1—C9	1.508 (2)	C15—C16	1.373 (3)
C1—H1A	0.9700	C15—H15	0.9300
C1—H1B	0.9700	C16—C17	1.374 (3)
N2—C11	1.3436 (16)	C16—H16	0.9300
N2—C3	1.4644 (15)	C17—C18	1.378 (2)
C3—C20	1.5265 (18)	C17—H17	0.9300
C3—C4	1.5368 (18)	C18—H18	0.9300
C3—H3	0.9800	C19—H19A	0.9600
C4—C10	1.5077 (17)	C19—H19B	0.9600
C4—C22	1.5211 (17)	C19—H19C	0.9600
C4—H4	0.9800	C20—O21	1.4079 (18)
C5—C6	1.383 (2)	C20—H20A	0.9700
C5—C10	1.3860 (19)	C20—H20B	0.9700
C5—H5	0.9300	O21—H21	0.90 (2)
C6—C7	1.372 (3)	C22—C27	1.385 (2)
C6—H6	0.9300	C22—C23	1.387 (2)
C7—C8	1.376 (3)	C23—C24	1.387 (2)
C7—H7	0.9300	C23—H23	0.9300
C8—C9	1.393 (2)	C24—C25	1.375 (3)
C8—H8	0.9300	C24—H24	0.9300
C9—C10	1.3932 (19)	C25—C26	1.375 (3)
C11—O12	1.2309 (16)	C25—H25	0.9300
C11—C13	1.4960 (19)	C26—C27	1.387 (2)
C13—C14	1.391 (2)	C26—H26	0.9300
C13—C18	1.395 (2)	C27—H27	0.9300
C14—C15	1.393 (3)
N2—C1—C9	113.86 (11)	C13—C14—C19	121.26 (16)
N2—C1—H1A	108.8	C15—C14—C19	120.96 (17)
C9—C1—H1A	108.8	C16—C15—C14	121.37 (17)
N2—C1—H1B	108.8	C16—C15—H15	119.3
C9—C1—H1B	108.8	C14—C15—H15	119.3
H1A—C1—H1B	107.7	C15—C16—C17	120.81 (17)
C11—N2—C1	119.23 (11)	C15—C16—H16	119.6
C11—N2—C3	124.56 (10)	C17—C16—H16	119.6
C1—N2—C3	116.20 (10)	C16—C17—C18	118.98 (18)
N2—C3—C20	111.52 (10)	C16—C17—H17	120.5
N2—C3—C4	108.33 (10)	C18—C17—H17	120.5
C20—C3—C4	111.52 (11)	C17—C18—C13	120.68 (16)
N2—C3—H3	108.5	C17—C18—H18	119.7
C20—C3—H3	108.5	C13—C18—H18	119.7
C4—C3—H3	108.5	C14—C19—H19A	109.5
C10—C4—C22	113.01 (10)	C14—C19—H19B	109.5
C10—C4—C3	109.42 (10)	H19A—C19—H19B	109.5
C22—C4—C3	111.92 (10)	C14—C19—H19C	109.5
C10—C4—H4	107.4	H19A—C19—H19C	109.5
C22—C4—H4	107.4	H19B—C19—H19C	109.5
C3—C4—H4	107.4	O21—C20—C3	112.22 (12)
C6—C5—C10	121.05 (14)	O21—C20—H20A	109.2
C6—C5—H5	119.5	C3—C20—H20A	109.2
C10—C5—H5	119.5	O21—C20—H20B	109.2
C7—C6—C5	119.42 (15)	C3—C20—H20B	109.2
C7—C6—H6	120.3	H20A—C20—H20B	107.9
C5—C6—H6	120.3	C20—O21—H21	107.8 (13)
C6—C7—C8	120.27 (14)	C27—C22—C23	118.78 (13)
C6—C7—H7	119.9	C27—C22—C4	122.15 (13)
C8—C7—H7	119.9	C23—C22—C4	119.07 (13)
C7—C8—C9	121.03 (15)	C22—C23—C24	120.39 (17)
C7—C8—H8	119.5	C22—C23—H23	119.8
C9—C8—H8	119.5	C24—C23—H23	119.8
C8—C9—C10	118.69 (14)	C25—C24—C23	120.32 (17)
C8—C9—C1	119.29 (13)	C25—C24—H24	119.8
C10—C9—C1	122.00 (12)	C23—C24—H24	119.8
C5—C10—C9	119.51 (12)	C24—C25—C26	119.80 (15)
C5—C10—C4	120.48 (12)	C24—C25—H25	120.1
C9—C10—C4	120.00 (12)	C26—C25—H25	120.1
O12—C11—N2	121.15 (13)	C25—C26—C27	120.13 (19)
O12—C11—C13	120.68 (12)	C25—C26—H26	119.9
N2—C11—C13	118.17 (10)	C27—C26—H26	119.9
C14—C13—C18	120.33 (14)	C22—C27—C26	120.58 (17)
C14—C13—C11	120.59 (13)	C22—C27—H27	119.7
C18—C13—C11	118.98 (12)	C26—C27—H27	119.7
C13—C14—C15	117.73 (16)
C9—C1—N2—C11	150.62 (12)	C3—N2—C11—C13	−1.16 (19)
C9—C1—N2—C3	−29.93 (18)	O12—C11—C13—C14	83.25 (18)
C11—N2—C3—C20	116.59 (14)	N2—C11—C13—C14	−97.40 (16)
C1—N2—C3—C20	−62.83 (15)	O12—C11—C13—C18	−93.08 (17)
C11—N2—C3—C4	−120.31 (13)	N2—C11—C13—C18	86.28 (16)
C1—N2—C3—C4	60.27 (15)	C18—C13—C14—C15	−3.5 (2)
N2—C3—C4—C10	−57.68 (13)	C11—C13—C14—C15	−179.76 (13)
C20—C3—C4—C10	65.42 (13)	C18—C13—C14—C19	174.19 (15)
N2—C3—C4—C22	68.38 (13)	C11—C13—C14—C19	−2.1 (2)
C20—C3—C4—C22	−168.52 (11)	C13—C14—C15—C16	3.0 (2)
C10—C5—C6—C7	−0.4 (2)	C19—C14—C15—C16	−174.72 (18)
C5—C6—C7—C8	0.8 (2)	C14—C15—C16—C17	−0.6 (3)
C6—C7—C8—C9	0.0 (2)	C15—C16—C17—C18	−1.2 (3)
C7—C8—C9—C10	−1.3 (2)	C16—C17—C18—C13	0.7 (2)
C7—C8—C9—C1	−179.47 (14)	C14—C13—C18—C17	1.7 (2)
N2—C1—C9—C8	176.57 (13)	C11—C13—C18—C17	178.08 (13)
N2—C1—C9—C10	−1.6 (2)	N2—C3—C20—O21	−67.49 (14)
C6—C5—C10—C9	−0.8 (2)	C4—C3—C20—O21	171.24 (10)
C6—C5—C10—C4	178.85 (13)	C10—C4—C22—C27	32.87 (17)
C8—C9—C10—C5	1.6 (2)	C3—C4—C22—C27	−91.20 (14)
C1—C9—C10—C5	179.78 (13)	C10—C4—C22—C23	−147.57 (13)
C8—C9—C10—C4	−178.03 (12)	C3—C4—C22—C23	88.35 (15)
C1—C9—C10—C4	0.13 (19)	C27—C22—C23—C24	−0.5 (2)
C22—C4—C10—C5	84.52 (15)	C4—C22—C23—C24	179.97 (14)
C3—C4—C10—C5	−150.04 (12)	C22—C23—C24—C25	0.4 (3)
C22—C4—C10—C9	−95.83 (14)	C23—C24—C25—C26	0.0 (3)
C3—C4—C10—C9	29.60 (15)	C24—C25—C26—C27	−0.3 (3)
C1—N2—C11—O12	−2.4 (2)	C23—C22—C27—C26	0.2 (2)
C3—N2—C11—O12	178.19 (13)	C4—C22—C27—C26	179.74 (14)
C1—N2—C11—C13	178.25 (13)	C25—C26—C27—C22	0.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O21—H21···O12^i	0.90 (2)	1.91 (2)	2.7907 (16)	165.0 (19)
C19—H19C···O21	0.96	2.54	3.290 (2)	135
C23—H23···O21^ii	0.93	2.52	3.2774 (19)	139

Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) x+1/2, −y+5/2, −z.