Crystal structure of (1S,2R)-2-[(3R,4S)-3-methyl-4-phenyl-1,2,3,4-tetra­hydro­isoquinolin-2-yl]-1,2-di­phenyl­ethanol

Ben Ali, K.; Retailleau, P.

doi:10.1107/S2056989019011964

Crystal structure of (1S,2R)-2-[(3R,4S)-3-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinolin-2-yl]-1,2-diphenylethanol

The title chiral β-amino alcohol was isolated as one of two diastereomeric β-amino alcohols, the title molecule being found to be the (S,R) diastereoisomer. In the crystal, molecules are packed in a herringbone manner parallel to (103) and (10 $\overline{3}$ ) via weak C—H

O and C—H

π(ring) interactions.

Keywords: crystal structure; chiral β-amino alcohol; tetrahydroisoquinoline; hydrogen bond; Hirshfeld surface analysis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019011964/ff2162sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019011964/ff2162Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019011964/ff2162Isup3.cml Supplementary material

CCDC reference: 1950166

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.038
wR factor = 0.083
Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C27      ..O19      .      99.90 Degree

Alert level G
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          1 Note
PLAT791_ALERT_4_G Model has Chirality at C3          (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C4          (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C18         (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C19         (Chiral SPGR)          S Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  10 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997); COLLECT (Hooft, 1998); cell refinement: CrysAlis PRO (Rigaku OD, 2019); data reduction: CrysAlis PRO (Rigaku OD, 2019); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2015b).

(1S,2R)-2-[(3R,4S)-3-Methyl-4-phenyl-1,2,3,4-tetrahydroisoquinolin-2-yl]-1,2-diphenylethanol top

Crystal data top

C₃₀H₂₉NO	D_x = 1.151 Mg m⁻³
M_r = 419.54	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 6302 reflections
a = 7.3009 (8) Å	θ = 2.0–24.2°
b = 11.0552 (11) Å	µ = 0.07 mm⁻¹
c = 30.006 (3) Å	T = 293 K
V = 2421.8 (4) Å³	Prism, colorless
Z = 4	0.59 × 0.45 × 0.35 mm
F(000) = 896

Data collection top

Nonius KappaCCD area detector diffractometer	4427 independent reflections
Radiation source: 1.5kW sealed tube	3948 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and φ scans	θ_max = 25.4°, θ_min = 2.7°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2019)	h = −8→8
T_min = 0.844, T_max = 1.000	k = −13→13
21751 measured reflections	l = −36→36

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.038	w = 1/[σ²(F_o²) + (0.0304P)² + 0.3321P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.083	(Δ/σ)_max < 0.001
S = 1.07	Δρ_max = 0.11 e Å⁻³
4425 reflections	Δρ_min = −0.11 e Å⁻³
295 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0139 (11)
Primary atom site location: dual	Absolute structure: Refined as an inversion twin.
Secondary atom site location: difference Fourier map

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.3286 (4)	−0.0015 (2)	0.21766 (7)	0.0459 (6)
H1A	0.428447	−0.038350	0.234113	0.053*
H1B	0.243483	−0.065133	0.209524	0.053*
N2	0.4019 (2)	0.05352 (14)	0.17689 (6)	0.0355 (4)
C3	0.5027 (3)	0.16552 (19)	0.18741 (7)	0.0400 (5)
H3	0.556815	0.195001	0.159563	0.046*
C4	0.3616 (3)	0.26023 (18)	0.20271 (7)	0.0379 (5)
H4	0.430488	0.329448	0.214349	0.044*
C5	0.1547 (3)	0.2891 (2)	0.26931 (7)	0.0471 (6)
H5	0.162708	0.372208	0.264993	0.054*
C6	0.0507 (3)	0.2447 (3)	0.30407 (8)	0.0553 (7)
H6	−0.009196	0.297836	0.323159	0.064*
C7	0.0357 (4)	0.1222 (3)	0.31050 (8)	0.0576 (7)
H7	−0.035474	0.092057	0.333677	0.066*
C8	0.1265 (3)	0.0443 (2)	0.28246 (8)	0.0518 (6)
H8	0.116921	−0.038604	0.287084	0.060*
C9	0.2328 (3)	0.0871 (2)	0.24723 (7)	0.0405 (5)
C10	0.2479 (3)	0.2114 (2)	0.24055 (7)	0.0383 (5)
C11	0.6589 (3)	0.1502 (2)	0.22101 (9)	0.0567 (7)
H11A	0.726198	0.224575	0.223262	0.068*
H11B	0.739191	0.086877	0.211187	0.068*
H11C	0.609065	0.129700	0.249634	0.068*
C12	0.2492 (3)	0.30571 (18)	0.16372 (7)	0.0400 (5)
C13	0.3195 (4)	0.3956 (2)	0.13673 (8)	0.0570 (7)
H13	0.431991	0.430129	0.143737	0.066*
C14	0.2254 (5)	0.4350 (3)	0.09946 (9)	0.0707 (9)
H14	0.275393	0.495164	0.081543	0.081*
C15	0.0593 (5)	0.3858 (3)	0.08888 (9)	0.0699 (9)
H15	−0.003927	0.412441	0.063832	0.080*
C16	−0.0138 (4)	0.2967 (3)	0.11542 (9)	0.0623 (7)
H16	−0.126869	0.262995	0.108399	0.072*
C17	0.0809 (3)	0.2573 (2)	0.15257 (8)	0.0488 (6)
H17	0.030362	0.197119	0.170385	0.056*
C18	0.5032 (3)	−0.03477 (18)	0.14947 (7)	0.0367 (5)
H18	0.600714	−0.070012	0.167776	0.042*
C19	0.3684 (3)	−0.13740 (19)	0.13610 (8)	0.0416 (5)
H19	0.338016	−0.182861	0.163143	0.048*
O19	0.2046 (2)	−0.08765 (16)	0.11933 (6)	0.0560 (5)
HOH	0.198 (4)	−0.016 (3)	0.1307 (9)	0.067*
C20	0.5896 (3)	0.02111 (19)	0.10855 (7)	0.0394 (5)
C21	0.4942 (4)	0.0997 (2)	0.08094 (8)	0.0553 (7)
H21	0.377223	0.125320	0.088719	0.064*
C22	0.5742 (5)	0.1398 (3)	0.04165 (9)	0.0730 (8)
H22	0.510686	0.192712	0.023154	0.084*
C23	0.7467 (5)	0.1018 (3)	0.02999 (10)	0.0778 (10)
H23	0.798359	0.127746	0.003312	0.089*
C24	0.8428 (4)	0.0263 (3)	0.05729 (10)	0.0685 (8)
H24	0.960600	0.001927	0.049589	0.079*
C25	0.7644 (3)	−0.0137 (2)	0.09627 (8)	0.0502 (6)
H25	0.830335	−0.065258	0.114775	0.058*
C26	0.4523 (3)	−0.22470 (19)	0.10333 (7)	0.0434 (5)
C27	0.4150 (4)	−0.2197 (2)	0.05843 (9)	0.0648 (8)
H27	0.330932	−0.163529	0.047712	0.075*
C28	0.5013 (5)	−0.2974 (3)	0.02915 (9)	0.0816 (10)
H28	0.474735	−0.293390	−0.001130	0.094*
C29	0.6252 (5)	−0.3798 (3)	0.04431 (11)	0.0786 (9)
H29	0.684240	−0.431168	0.024431	0.090*
C30	0.6622 (4)	−0.3865 (2)	0.08887 (11)	0.0693 (8)
H30	0.746120	−0.442975	0.099374	0.080*
C31	0.5752 (4)	−0.3097 (2)	0.11835 (9)	0.0533 (6)
H31	0.599963	−0.315488	0.148673	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0562 (15)	0.0388 (12)	0.0426 (13)	−0.0048 (11)	0.0068 (11)	0.0038 (10)
N2	0.0361 (10)	0.0336 (8)	0.0369 (9)	−0.0008 (8)	0.0058 (8)	0.0001 (7)
C3	0.0384 (12)	0.0391 (11)	0.0426 (12)	−0.0037 (10)	0.0039 (10)	−0.0003 (9)
C4	0.0419 (13)	0.0322 (10)	0.0395 (12)	−0.0059 (10)	0.0006 (10)	−0.0037 (9)
C5	0.0441 (13)	0.0536 (14)	0.0437 (13)	0.0038 (11)	−0.0043 (11)	−0.0078 (11)
C6	0.0421 (14)	0.0826 (19)	0.0413 (13)	0.0074 (14)	0.0005 (11)	−0.0127 (13)
C7	0.0482 (15)	0.0850 (19)	0.0395 (13)	−0.0076 (14)	0.0064 (12)	0.0015 (13)
C8	0.0552 (15)	0.0596 (14)	0.0406 (13)	−0.0126 (13)	0.0031 (12)	0.0036 (11)
C9	0.0423 (13)	0.0472 (12)	0.0320 (11)	−0.0030 (11)	0.0010 (10)	0.0002 (9)
C10	0.0364 (12)	0.0442 (12)	0.0342 (11)	0.0002 (10)	−0.0019 (10)	−0.0030 (9)
C11	0.0433 (14)	0.0589 (15)	0.0680 (17)	−0.0014 (12)	−0.0081 (13)	−0.0064 (13)
C12	0.0494 (14)	0.0319 (10)	0.0387 (12)	0.0043 (11)	0.0068 (10)	−0.0036 (9)
C13	0.0653 (17)	0.0470 (13)	0.0586 (16)	−0.0024 (13)	0.0074 (14)	0.0085 (12)
C14	0.093 (2)	0.0637 (17)	0.0558 (17)	0.0100 (18)	0.0123 (17)	0.0203 (14)
C15	0.091 (2)	0.0766 (19)	0.0426 (15)	0.0331 (19)	−0.0020 (15)	0.0037 (14)
C16	0.0589 (16)	0.0737 (17)	0.0544 (16)	0.0111 (15)	−0.0078 (14)	−0.0108 (14)
C17	0.0526 (15)	0.0485 (13)	0.0452 (13)	0.0024 (12)	−0.0009 (11)	0.0013 (11)
C18	0.0336 (11)	0.0391 (11)	0.0375 (11)	0.0034 (10)	−0.0016 (10)	0.0010 (9)
C19	0.0396 (12)	0.0390 (11)	0.0463 (13)	0.0003 (10)	−0.0006 (10)	−0.0009 (10)
O19	0.0414 (9)	0.0551 (10)	0.0715 (12)	0.0037 (8)	−0.0092 (9)	−0.0069 (9)
C20	0.0415 (13)	0.0403 (11)	0.0364 (12)	−0.0010 (10)	0.0015 (10)	−0.0042 (9)
C21	0.0617 (17)	0.0595 (14)	0.0448 (14)	0.0047 (14)	0.0015 (12)	0.0049 (12)
C22	0.097 (2)	0.0752 (19)	0.0467 (15)	−0.0039 (19)	−0.0026 (17)	0.0129 (14)
C23	0.095 (3)	0.091 (2)	0.0469 (16)	−0.024 (2)	0.0244 (17)	−0.0042 (16)
C24	0.0622 (18)	0.082 (2)	0.0616 (18)	−0.0138 (17)	0.0209 (15)	−0.0176 (16)
C25	0.0452 (14)	0.0532 (14)	0.0522 (15)	−0.0035 (12)	0.0073 (11)	−0.0090 (11)
C26	0.0456 (14)	0.0384 (11)	0.0461 (13)	−0.0055 (11)	−0.0012 (11)	−0.0046 (10)
C27	0.086 (2)	0.0577 (15)	0.0507 (16)	0.0103 (16)	−0.0131 (15)	−0.0060 (12)
C28	0.122 (3)	0.076 (2)	0.0477 (16)	0.007 (2)	−0.0009 (18)	−0.0158 (15)
C29	0.095 (2)	0.0622 (18)	0.078 (2)	0.0071 (19)	0.0216 (19)	−0.0239 (16)
C30	0.069 (2)	0.0568 (16)	0.082 (2)	0.0137 (15)	0.0011 (17)	−0.0151 (15)
C31	0.0581 (16)	0.0453 (12)	0.0563 (15)	0.0058 (12)	−0.0049 (13)	−0.0066 (11)

Geometric parameters (Å, º) top

C1—N2	1.467 (3)	C16—C17	1.382 (3)
C1—C9	1.496 (3)	C16—H16	0.9300
C1—H1A	0.9700	C17—H17	0.9300
C1—H1B	0.9700	C18—C20	1.512 (3)
N2—C3	1.475 (3)	C18—C19	1.555 (3)
N2—C18	1.475 (3)	C18—H18	0.9800
C3—C11	1.531 (3)	C19—O19	1.409 (3)
C3—C4	1.539 (3)	C19—C26	1.508 (3)
C3—H3	0.9800	C19—H19	0.9800
C4—C10	1.507 (3)	O19—HOH	0.86 (3)
C4—C12	1.515 (3)	C20—C25	1.383 (3)
C4—H4	0.9800	C20—C21	1.388 (3)
C5—C6	1.380 (3)	C21—C22	1.389 (4)
C5—C10	1.395 (3)	C21—H21	0.9300
C5—H5	0.9300	C22—C23	1.373 (4)
C6—C7	1.372 (4)	C22—H22	0.9300
C6—H6	0.9300	C23—C24	1.364 (4)
C7—C8	1.374 (4)	C23—H23	0.9300
C7—H7	0.9300	C24—C25	1.375 (4)
C8—C9	1.394 (3)	C24—H24	0.9300
C8—H8	0.9300	C25—H25	0.9300
C9—C10	1.393 (3)	C26—C31	1.375 (3)
C11—H11A	0.9600	C26—C27	1.376 (3)
C11—H11B	0.9600	C27—C28	1.381 (4)
C11—H11C	0.9600	C27—H27	0.9300
C12—C13	1.380 (3)	C28—C29	1.362 (4)
C12—C17	1.381 (3)	C28—H28	0.9300
C13—C14	1.383 (4)	C29—C30	1.366 (4)
C13—H13	0.9300	C29—H29	0.9300
C14—C15	1.367 (4)	C30—C31	1.381 (4)
C14—H14	0.9300	C30—H30	0.9300
C15—C16	1.374 (4)	C31—H31	0.9300
C15—H15	0.9300

N2—C1—C9	113.18 (17)	C16—C15—H15	120.2
N2—C1—H1A	108.9	C15—C16—C17	119.9 (3)
C9—C1—H1A	108.9	C15—C16—H16	120.0
N2—C1—H1B	108.9	C17—C16—H16	120.0
C9—C1—H1B	108.9	C12—C17—C16	121.2 (2)
H1A—C1—H1B	107.8	C12—C17—H17	119.4
C1—N2—C3	110.59 (16)	C16—C17—H17	119.4
C1—N2—C18	111.93 (16)	N2—C18—C20	113.06 (16)
C3—N2—C18	115.13 (16)	N2—C18—C19	108.02 (16)
N2—C3—C11	114.83 (18)	C20—C18—C19	110.66 (17)
N2—C3—C4	107.52 (17)	N2—C18—H18	108.3
C11—C3—C4	112.15 (18)	C20—C18—H18	108.3
N2—C3—H3	107.3	C19—C18—H18	108.3
C11—C3—H3	107.3	O19—C19—C26	111.22 (19)
C4—C3—H3	107.3	O19—C19—C18	110.15 (17)
C10—C4—C12	113.71 (18)	C26—C19—C18	112.22 (18)
C10—C4—C3	110.49 (17)	O19—C19—H19	107.7
C12—C4—C3	110.99 (17)	C26—C19—H19	107.7
C10—C4—H4	107.1	C18—C19—H19	107.7
C12—C4—H4	107.1	C19—O19—HOH	105 (2)
C3—C4—H4	107.1	C25—C20—C21	118.6 (2)
C6—C5—C10	121.1 (2)	C25—C20—C18	119.2 (2)
C6—C5—H5	119.4	C21—C20—C18	122.1 (2)
C10—C5—H5	119.4	C20—C21—C22	119.7 (3)
C7—C6—C5	120.1 (2)	C20—C21—H21	120.1
C7—C6—H6	120.0	C22—C21—H21	120.1
C5—C6—H6	120.0	C23—C22—C21	120.3 (3)
C6—C7—C8	119.6 (2)	C23—C22—H22	119.9
C6—C7—H7	120.2	C21—C22—H22	119.9
C8—C7—H7	120.2	C24—C23—C22	120.4 (3)
C7—C8—C9	121.3 (2)	C24—C23—H23	119.8
C7—C8—H8	119.3	C22—C23—H23	119.8
C9—C8—H8	119.3	C23—C24—C25	119.5 (3)
C10—C9—C8	119.2 (2)	C23—C24—H24	120.2
C10—C9—C1	121.60 (19)	C25—C24—H24	120.2
C8—C9—C1	119.2 (2)	C24—C25—C20	121.4 (3)
C9—C10—C5	118.7 (2)	C24—C25—H25	119.3
C9—C10—C4	120.36 (19)	C20—C25—H25	119.3
C5—C10—C4	121.0 (2)	C31—C26—C27	118.6 (2)
C3—C11—H11A	109.5	C31—C26—C19	119.3 (2)
C3—C11—H11B	109.5	C27—C26—C19	122.2 (2)
H11A—C11—H11B	109.5	C26—C27—C28	120.5 (3)
C3—C11—H11C	109.5	C26—C27—H27	119.8
H11A—C11—H11C	109.5	C28—C27—H27	119.8
H11B—C11—H11C	109.5	C29—C28—C27	120.4 (3)
C13—C12—C17	117.9 (2)	C29—C28—H28	119.8
C13—C12—C4	119.3 (2)	C27—C28—H28	119.8
C17—C12—C4	122.7 (2)	C28—C29—C30	119.7 (3)
C12—C13—C14	121.1 (3)	C28—C29—H29	120.2
C12—C13—H13	119.5	C30—C29—H29	120.2
C14—C13—H13	119.5	C29—C30—C31	120.2 (3)
C15—C14—C13	120.2 (3)	C29—C30—H30	119.9
C15—C14—H14	119.9	C31—C30—H30	119.9
C13—C14—H14	119.9	C26—C31—C30	120.7 (3)
C14—C15—C16	119.7 (3)	C26—C31—H31	119.7
C14—C15—H15	120.2	C30—C31—H31	119.7

C9—C1—N2—C3	47.4 (2)	C13—C12—C17—C16	0.5 (3)
C9—C1—N2—C18	177.26 (19)	C4—C12—C17—C16	−176.6 (2)
C1—N2—C3—C11	56.3 (2)	C15—C16—C17—C12	−0.1 (4)
C18—N2—C3—C11	−71.7 (2)	C1—N2—C18—C20	−176.66 (18)
C1—N2—C3—C4	−69.2 (2)	C3—N2—C18—C20	−49.2 (2)
C18—N2—C3—C4	162.68 (16)	C1—N2—C18—C19	60.5 (2)
N2—C3—C4—C10	54.4 (2)	C3—N2—C18—C19	−172.04 (17)
C11—C3—C4—C10	−72.8 (2)	N2—C18—C19—O19	48.5 (2)
N2—C3—C4—C12	−72.7 (2)	C20—C18—C19—O19	−75.7 (2)
C11—C3—C4—C12	160.16 (19)	N2—C18—C19—C26	173.03 (17)
C10—C5—C6—C7	−0.8 (4)	C20—C18—C19—C26	48.8 (2)
C5—C6—C7—C8	0.8 (4)	N2—C18—C20—C25	138.8 (2)
C6—C7—C8—C9	−0.6 (4)	C19—C18—C20—C25	−99.9 (2)
C7—C8—C9—C10	0.4 (4)	N2—C18—C20—C21	−46.1 (3)
C7—C8—C9—C1	−179.9 (2)	C19—C18—C20—C21	75.2 (2)
N2—C1—C9—C10	−12.7 (3)	C25—C20—C21—C22	1.0 (4)
N2—C1—C9—C8	167.7 (2)	C18—C20—C21—C22	−174.2 (2)
C8—C9—C10—C5	−0.4 (3)	C20—C21—C22—C23	0.2 (4)
C1—C9—C10—C5	179.9 (2)	C21—C22—C23—C24	−1.4 (5)
C8—C9—C10—C4	−179.9 (2)	C22—C23—C24—C25	1.3 (4)
C1—C9—C10—C4	0.4 (3)	C23—C24—C25—C20	−0.1 (4)
C6—C5—C10—C9	0.6 (3)	C21—C20—C25—C24	−1.1 (3)
C6—C5—C10—C4	−179.8 (2)	C18—C20—C25—C24	174.2 (2)
C12—C4—C10—C9	104.1 (2)	O19—C19—C26—C31	−159.3 (2)
C3—C4—C10—C9	−21.5 (3)	C18—C19—C26—C31	76.8 (3)
C12—C4—C10—C5	−75.4 (2)	O19—C19—C26—C27	23.1 (3)
C3—C4—C10—C5	159.02 (19)	C18—C19—C26—C27	−100.8 (3)
C10—C4—C12—C13	152.5 (2)	C31—C26—C27—C28	−0.9 (4)
C3—C4—C12—C13	−82.2 (2)	C19—C26—C27—C28	176.8 (3)
C10—C4—C12—C17	−30.5 (3)	C26—C27—C28—C29	−0.2 (5)
C3—C4—C12—C17	94.8 (2)	C27—C28—C29—C30	0.9 (5)
C17—C12—C13—C14	−0.7 (4)	C28—C29—C30—C31	−0.4 (5)
C4—C12—C13—C14	176.5 (2)	C27—C26—C31—C30	1.4 (4)
C12—C13—C14—C15	0.5 (4)	C19—C26—C31—C30	−176.4 (2)
C13—C14—C15—C16	−0.1 (4)	C29—C30—C31—C26	−0.8 (4)
C14—C15—C16—C17	−0.1 (4)

Hydrogen-bond geometry (Å, º) top

Cg2, Cg3, Cg4 and Cg5 are the centroids of the C5–C10, C12-C17, C20–C25, and C26–C31 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O19—HOH···N2	0.86 (3)	2.18 (3)	2.737 (2)	123 (2)
C27—H27···O19	0.93	2.48	2.798 (3)	100
C21—H21···Cg3	0.93	3.14	3.930 (4)	144
C6—H6···O19ⁱ	0.93	2.57	3.492 (3)	170
C14—H14···Cg5ⁱⁱ	0.93	2.95	3.770 (4)	147
C16—H16···Cg4ⁱⁱⁱ	0.93	2.92	3.743 (3)	148
C31—H31···Cg2^iv	0.93	2.96	3.803 (3)	152

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

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Crystal structure of (1S,2R)-2-[(3R,4S)-3-methyl-4-phenyl-1,2,3,4-tetra­hydro­isoquinolin-2-yl]-1,2-di­phenyl­ethanol

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structure of (1S,2R)-2-[(3R,4S)-3-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinolin-2-yl]-1,2-diphenylethanol