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

The spectroscopically uncharacterized title compound, C₂₂H₂₇NO, was isolated as one of two diastereoisomeric β-aminoalcohols. By reference to two unchanging chiral C atoms of the cyclo­hexa­nol group, the mol­ecule was found to be the S,S diastereoisomer.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.047
• wR factor = 0.119
• Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



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           28.73
           From the CIF: _reflns_number_total               2698
           Count of symmetry unique reflns         2720
           Completeness (_total/calc)             99.19%
           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
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C18    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C23    = .          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   7 ALERT level G = General alerts; check

   6 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: COLLECT (Nonius, 1997); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

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

Crystal data

C22H27NO	Dx = 1.166 Mg m^−3
Mr = 321.45	Melting point: 394 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2651 reflections
a = 7.060 (4) Å	θ = 1.0–28.7°
b = 11.282 (6) Å	µ = 0.07 mm^−1
c = 22.982 (8) Å	T = 293 K
V = 1830.5 (16) Å^3	Prism, colourless
Z = 4	0.58 × 0.58 × 0.25 mm
F(000) = 696

Data collection

Nonius KappaCCD area-detector diffractometer	2698 independent reflections
Radiation source: fine-focus sealed tube	2108 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 28.7°, θmin = 1.8°
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	h = −9→9
Tmin = 0.910, Tmax = 0.980	k = −15→15
4682 measured reflections	l = −30→31

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: difference Fourier map
wR(F^2) = 0.119	H-atom parameters constrained
S = 1.17	w = 1/[σ^2(Fo^2) + (0.0423P)^2 + 0.2467P] where P = (Fo^2 + 2Fc^2)/3
2698 reflections	(Δ/σ)max = 0.001
219 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

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	0.2274 (4)	0.5915 (2)	0.16424 (10)	0.0554 (6)
H1A	0.3252	0.6513	0.1682	0.064*
H1B	0.1433	0.5986	0.1974	0.064*
N2	0.3154 (2)	0.47467 (15)	0.16525 (7)	0.0439 (4)
C3	0.4023 (3)	0.4426 (2)	0.10928 (9)	0.0480 (5)
H3	0.4635	0.3653	0.1144	0.055*
C4	0.2403 (3)	0.4261 (2)	0.06485 (8)	0.0461 (5)
H4	0.2990	0.4155	0.0266	0.053*
C5	0.0249 (3)	0.5680 (2)	0.01145 (9)	0.0529 (6)
H5	0.0289	0.5171	−0.0203	0.061*
C6	−0.0786 (3)	0.6714 (2)	0.00786 (10)	0.0599 (6)
H6	−0.1433	0.6901	−0.0262	0.069*
C7	−0.0856 (4)	0.7469 (2)	0.05488 (11)	0.0610 (6)
H7	−0.1555	0.8166	0.0527	0.070*
C8	0.0112 (3)	0.7190 (2)	0.10542 (11)	0.0567 (6)
H8	0.0057	0.7702	0.1371	0.065*
C9	0.1162 (3)	0.61548 (19)	0.10947 (9)	0.0461 (5)
C10	0.1240 (3)	0.5385 (2)	0.06206 (8)	0.0444 (5)
C11	0.5520 (4)	0.5279 (3)	0.08579 (11)	0.0725 (8)
H11A	0.6050	0.4963	0.0506	0.087*
H11B	0.6505	0.5377	0.1142	0.087*
H11C	0.4945	0.6033	0.0778	0.087*
C12	0.1259 (3)	0.3157 (2)	0.07727 (8)	0.0454 (5)
C13	0.1825 (4)	0.2070 (2)	0.05487 (10)	0.0597 (6)
H13	0.2876	0.2035	0.0306	0.069*
C14	0.0858 (5)	0.1038 (2)	0.06791 (10)	0.0686 (7)
H14	0.1271	0.0321	0.0526	0.079*
C15	−0.0700 (5)	0.1066 (2)	0.10318 (12)	0.0710 (7)
H15	−0.1348	0.0371	0.1120	0.082*
C16	−0.1297 (4)	0.2129 (2)	0.12545 (12)	0.0693 (7)
H16	−0.2358	0.2154	0.1494	0.080*
C17	−0.0333 (3)	0.3165 (2)	0.11256 (10)	0.0569 (6)
H17	−0.0761	0.3880	0.1279	0.065*
C18	0.4318 (3)	0.4506 (2)	0.21706 (9)	0.0503 (5)
H18	0.5064	0.3796	0.2083	0.058*
C19	0.5730 (4)	0.5457 (3)	0.23702 (12)	0.0799 (9)
H19A	0.6556	0.5668	0.2049	0.092*
H19B	0.5046	0.6163	0.2489	0.092*
C20	0.6920 (4)	0.5000 (4)	0.28801 (12)	0.0901 (10)
H20A	0.7661	0.4322	0.2755	0.104*
H20B	0.7790	0.5614	0.3005	0.104*
C21	0.5674 (5)	0.4645 (3)	0.33814 (11)	0.0752 (8)
H21A	0.5058	0.5344	0.3539	0.087*
H21B	0.6446	0.4299	0.3686	0.087*
C22	0.4189 (5)	0.3762 (2)	0.31941 (10)	0.0703 (7)
H22A	0.3341	0.3610	0.3518	0.081*
H22B	0.4803	0.3021	0.3093	0.081*
C23	0.3046 (4)	0.4190 (2)	0.26795 (9)	0.0555 (6)
H23	0.2341	0.4900	0.2796	0.064*
O24	0.1726 (3)	0.3293 (2)	0.25220 (8)	0.0876 (7)
H24	0.1583	0.3294	0.2168	0.105*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0586 (13)	0.0515 (13)	0.0560 (11)	0.0085 (11)	−0.0161 (11)	−0.0022 (11)
N2	0.0402 (8)	0.0497 (10)	0.0417 (8)	0.0033 (8)	−0.0035 (8)	0.0034 (8)
C3	0.0375 (10)	0.0585 (13)	0.0481 (10)	0.0027 (10)	0.0002 (9)	0.0039 (10)
C4	0.0406 (10)	0.0579 (13)	0.0398 (9)	−0.0005 (10)	0.0031 (9)	0.0017 (9)
C5	0.0449 (11)	0.0687 (15)	0.0450 (10)	−0.0067 (12)	−0.0025 (10)	0.0129 (11)
C6	0.0484 (12)	0.0735 (16)	0.0578 (12)	−0.0055 (13)	−0.0097 (11)	0.0237 (12)
C7	0.0506 (13)	0.0561 (13)	0.0763 (15)	0.0055 (12)	−0.0087 (13)	0.0180 (12)
C8	0.0533 (13)	0.0509 (13)	0.0660 (13)	0.0021 (11)	−0.0070 (12)	0.0043 (12)
C9	0.0398 (10)	0.0481 (11)	0.0503 (10)	−0.0025 (9)	−0.0044 (10)	0.0080 (10)
C10	0.0344 (10)	0.0534 (12)	0.0453 (10)	−0.0054 (9)	−0.0002 (9)	0.0098 (9)
C11	0.0451 (12)	0.106 (2)	0.0661 (15)	−0.0157 (16)	0.0022 (12)	0.0162 (15)
C12	0.0453 (11)	0.0505 (12)	0.0404 (9)	0.0037 (10)	−0.0059 (9)	−0.0016 (9)
C13	0.0664 (15)	0.0627 (15)	0.0499 (11)	0.0104 (14)	−0.0024 (12)	−0.0094 (11)
C14	0.094 (2)	0.0504 (14)	0.0619 (14)	0.0063 (15)	−0.0147 (15)	−0.0095 (12)
C15	0.0855 (19)	0.0518 (14)	0.0756 (15)	−0.0105 (15)	−0.0133 (17)	0.0044 (14)
C16	0.0628 (16)	0.0615 (16)	0.0837 (17)	−0.0094 (14)	0.0083 (15)	0.0032 (13)
C17	0.0520 (13)	0.0484 (13)	0.0702 (14)	0.0013 (11)	0.0074 (12)	−0.0018 (11)
C18	0.0474 (11)	0.0548 (13)	0.0487 (11)	0.0064 (12)	−0.0080 (10)	0.0058 (10)
C19	0.0671 (17)	0.105 (2)	0.0680 (15)	−0.0285 (18)	−0.0261 (14)	0.0213 (16)
C20	0.0689 (17)	0.126 (3)	0.0755 (17)	−0.014 (2)	−0.0309 (16)	0.0129 (18)
C21	0.0812 (18)	0.0871 (19)	0.0573 (13)	0.0080 (17)	−0.0211 (14)	0.0062 (14)
C22	0.0889 (19)	0.0678 (16)	0.0541 (12)	0.0051 (17)	−0.0093 (14)	0.0136 (12)
C23	0.0591 (13)	0.0580 (14)	0.0495 (11)	0.0019 (13)	−0.0046 (11)	0.0049 (10)
O24	0.0972 (15)	0.0973 (15)	0.0683 (11)	−0.0401 (14)	−0.0130 (12)	0.0218 (11)

Geometric parameters (Å, º)

C1—N2	1.457 (3)	C13—C14	1.382 (4)
C1—C9	1.508 (3)	C13—H13	0.9300
C1—H1A	0.9700	C14—C15	1.367 (4)
C1—H1B	0.9700	C14—H14	0.9300
N2—C3	1.470 (3)	C15—C16	1.370 (4)
N2—C18	1.472 (3)	C15—H15	0.9300
C3—C11	1.528 (3)	C16—C17	1.385 (3)
C3—C4	1.545 (3)	C16—H16	0.9300
C3—H3	0.9800	C17—H17	0.9300
C4—C10	1.511 (3)	C18—C23	1.518 (3)
C4—C12	1.511 (3)	C18—C19	1.534 (3)
C4—H4	0.9800	C18—H18	0.9800
C5—C6	1.379 (3)	C19—C20	1.532 (4)
C5—C10	1.397 (3)	C19—H19A	0.9700
C5—H5	0.9300	C19—H19B	0.9700
C6—C7	1.377 (3)	C20—C21	1.504 (4)
C6—H6	0.9300	C20—H20A	0.9700
C7—C8	1.384 (3)	C20—H20B	0.9700
C7—H7	0.9300	C21—C22	1.509 (4)
C8—C9	1.386 (3)	C21—H21A	0.9700
C8—H8	0.9300	C21—H21B	0.9700
C9—C10	1.395 (3)	C22—C23	1.511 (3)
C11—H11A	0.9600	C22—H22A	0.9700
C11—H11B	0.9600	C22—H22B	0.9700
C11—H11C	0.9600	C23—O24	1.422 (3)
C12—C17	1.386 (3)	C23—H23	0.9800
C12—C13	1.389 (3)	O24—H24	0.8200
N2—C1—C9	113.45 (18)	C12—C13—H13	119.3
N2—C1—H1A	108.9	C15—C14—C13	120.5 (3)
C9—C1—H1A	108.9	C15—C14—H14	119.8
N2—C1—H1B	108.9	C13—C14—H14	119.8
C9—C1—H1B	108.9	C14—C15—C16	119.3 (3)
H1A—C1—H1B	107.7	C14—C15—H15	120.4
C1—N2—C3	112.75 (17)	C16—C15—H15	120.4
C1—N2—C18	114.69 (17)	C15—C16—C17	120.5 (3)
C3—N2—C18	115.44 (16)	C15—C16—H16	119.8
N2—C3—C11	116.3 (2)	C17—C16—H16	119.8
N2—C3—C4	107.40 (16)	C16—C17—C12	121.2 (2)
C11—C3—C4	110.76 (17)	C16—C17—H17	119.4
N2—C3—H3	107.4	C12—C17—H17	119.4
C11—C3—H3	107.4	N2—C18—C23	109.66 (18)
C4—C3—H3	107.4	N2—C18—C19	118.41 (19)
C10—C4—C12	114.15 (17)	C23—C18—C19	108.58 (19)
C10—C4—C3	109.23 (18)	N2—C18—H18	106.5
C12—C4—C3	111.71 (17)	C23—C18—H18	106.5
C10—C4—H4	107.1	C19—C18—H18	106.5
C12—C4—H4	107.1	C20—C19—C18	110.5 (2)
C3—C4—H4	107.1	C20—C19—H19A	109.6
C6—C5—C10	121.1 (2)	C18—C19—H19A	109.6
C6—C5—H5	119.4	C20—C19—H19B	109.6
C10—C5—H5	119.4	C18—C19—H19B	109.6
C7—C6—C5	119.7 (2)	H19A—C19—H19B	108.1
C7—C6—H6	120.2	C21—C20—C19	110.8 (2)
C5—C6—H6	120.2	C21—C20—H20A	109.5
C6—C7—C8	120.0 (2)	C19—C20—H20A	109.5
C6—C7—H7	120.0	C21—C20—H20B	109.5
C8—C7—H7	120.0	C19—C20—H20B	109.5
C7—C8—C9	120.8 (2)	H20A—C20—H20B	108.1
C7—C8—H8	119.6	C20—C21—C22	111.3 (2)
C9—C8—H8	119.6	C20—C21—H21A	109.4
C8—C9—C10	119.6 (2)	C22—C21—H21A	109.4
C8—C9—C1	119.1 (2)	C20—C21—H21B	109.4
C10—C9—C1	121.30 (19)	C22—C21—H21B	109.4
C9—C10—C5	118.8 (2)	H21A—C21—H21B	108.0
C9—C10—C4	120.72 (18)	C21—C22—C23	112.6 (2)
C5—C10—C4	120.5 (2)	C21—C22—H22A	109.1
C3—C11—H11A	109.5	C23—C22—H22A	109.1
C3—C11—H11B	109.5	C21—C22—H22B	109.1
H11A—C11—H11B	109.5	C23—C22—H22B	109.1
C3—C11—H11C	109.5	H22A—C22—H22B	107.8
H11A—C11—H11C	109.5	O24—C23—C22	108.8 (2)
H11B—C11—H11C	109.5	O24—C23—C18	111.04 (19)
C17—C12—C13	117.1 (2)	C22—C23—C18	111.2 (2)
C17—C12—C4	122.6 (2)	O24—C23—H23	108.6
C13—C12—C4	120.3 (2)	C22—C23—H23	108.6
C14—C13—C12	121.4 (2)	C18—C23—H23	108.6
C14—C13—H13	119.3	C23—O24—H24	109.5
C9—C1—N2—C3	42.6 (3)	C10—C4—C12—C17	−33.5 (3)
C9—C1—N2—C18	177.45 (19)	C3—C4—C12—C17	91.0 (2)
C1—N2—C3—C11	56.9 (2)	C10—C4—C12—C13	148.90 (19)
C18—N2—C3—C11	−77.6 (2)	C3—C4—C12—C13	−86.6 (2)
C1—N2—C3—C4	−67.7 (2)	C17—C12—C13—C14	−0.9 (3)
C18—N2—C3—C4	157.76 (18)	C4—C12—C13—C14	176.8 (2)
N2—C3—C4—C10	56.7 (2)	C12—C13—C14—C15	0.5 (4)
C11—C3—C4—C10	−71.2 (2)	C13—C14—C15—C16	0.1 (4)
N2—C3—C4—C12	−70.5 (2)	C14—C15—C16—C17	−0.1 (4)
C11—C3—C4—C12	161.6 (2)	C15—C16—C17—C12	−0.4 (4)
C10—C5—C6—C7	−0.3 (3)	C13—C12—C17—C16	0.9 (3)
C5—C6—C7—C8	0.1 (4)	C4—C12—C17—C16	−176.8 (2)
C6—C7—C8—C9	0.1 (4)	C1—N2—C18—C23	78.7 (2)
C7—C8—C9—C10	−0.1 (3)	C3—N2—C18—C23	−147.69 (19)
C7—C8—C9—C1	177.0 (2)	C1—N2—C18—C19	−46.6 (3)
N2—C1—C9—C8	174.07 (19)	C3—N2—C18—C19	87.0 (3)
N2—C1—C9—C10	−8.9 (3)	N2—C18—C19—C20	−175.0 (2)
C8—C9—C10—C5	0.0 (3)	C23—C18—C19—C20	59.1 (3)
C1—C9—C10—C5	−177.1 (2)	C18—C19—C20—C21	−58.2 (4)
C8—C9—C10—C4	178.90 (19)	C19—C20—C21—C22	54.5 (4)
C1—C9—C10—C4	1.8 (3)	C20—C21—C22—C23	−53.5 (3)
C6—C5—C10—C9	0.2 (3)	C21—C22—C23—O24	178.3 (2)
C6—C5—C10—C4	−178.67 (19)	C21—C22—C23—C18	55.6 (3)
C12—C4—C10—C9	100.0 (2)	N2—C18—C23—O24	50.3 (3)
C3—C4—C10—C9	−25.9 (3)	C19—C18—C23—O24	−178.9 (2)
C12—C4—C10—C5	−81.1 (2)	N2—C18—C23—C22	171.6 (2)
C3—C4—C10—C5	153.01 (18)	C19—C18—C23—C22	−57.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O24—H24···N2	0.82	2.32	2.774 (2)	117