Absolute configuration of N-[(R)-3-methyl-2-butyl]-(S)-2-(6-methoxy-2-naphthyl)­propion­amide

Dupont, L.; Khelili, S.; Pirotte, B.; Tinant, B.; De Tullio, P.

doi:10.1107/S1600536801010285

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Absolute configuration of N-[(R)-3-methyl-2-butyl]-(S)-2-(6-methoxy-2-naphthyl)propionamide

L. Dupont, S. Khelili, B. Pirotte, B. Tinant and P. De Tullio

The title compound, C₁₉H₂₅NO₂, was made in order to confirm the absolute configuration of (R)-3-methyl-2-butylamine obtained from commercially available (R/S)-3-methyl-2-butylamine (racemate) after fractional crystallization of its ammonium salt with the optically pure carboxylic acid derivative, (S)-naproxene.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801010285/wn6026sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801010285/wn6026Isup2.hkl Contains datablock I

CCDC reference: 170785

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.053
wR factor = 0.149
Data-to-parameter ratio = 13.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



STRVAL_01
         From the CIF: _refine_ls_abs_structure_Flack   -0.300
         From the CIF: _refine_ls_abs_structure_Flack_su    1.200
           Alert C Flack parameter is too small

THETM_01  Alert C The value of sine(theta_max)/wavelength is less than 0.590
          Calculated sin(theta_max)/wavelength =    0.5815

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           24.41
         From the CIF: _reflns_number_total               5448
         Count of symmetry unique reflns         2860
         Completeness (_total/calc)            190.49%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      2588
         Fraction of Friedel pairs measured     0.905
         Are heavy atom types Z>Si present           no
          ALERT: MoKa measured Friedel data cannot be used to
                 determine absolute structure in a light-atom
                 study EXCEPT under VERY special conditions.
                 It is preferred that Friedel data is merged in such cases.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

Comment top

(R)-3-Methyl-2-butylamine reacted with succinimidyl (S)-(6-methoxynaphth-2-yl)propionate to form the corresponding amide, i.e. the title compound, (I). The Flack (1983) parameter -0.3 (12) calculated after crystal structure refinement does not allow us to determine reliably the absolute configuration. Nevertheless, since the product was prepared from (S)-naproxene, the C12A and C12B atoms have an S configuration and the chirality of C15A and C15B, deduced from the torsional angles, is R. The stacking of the molecules is the result of van der Waals contacts, and of N1A—H···O2B and N1B—H···O2Aⁱ [symmetry code: (i) 1 + x, y, 1 + z] hydrogen bonds. Molecules A and B form infinite ABABAB··· chains in a direction parallel to the diagonal of the a and c axes.

Experimental top

The preparation of the title compound is described in Khelili et al. (1999). Crystals were obtained by slow evaporation of a methanol solution.

Computing details top

Cell refinement: marHKL (Klein & Bartels, 2000); data reduction: marHKL (Klein & Bartels, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. The molecular structure with atom-labelling schemes of molecules A and B. Displacement ellipsoids are shown at 50% probability levels and H atoms are drawn as small circles of arbitrary radii.

N-[(R)-3-methyl-2-butyl]-(S)-2-(6-methoxy-2-naphthyl)propionamide top

Crystal data top

C₁₉H₂₅NO₂	F(000) = 648
M_r = 299.40	D_x = 1.164 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71069 Å
a = 6.879 (2) Å	Cell parameters from 133 reflections
b = 29.563 (9) Å	θ = 2.5–24.5°
c = 8.511 (3) Å	µ = 0.08 mm⁻¹
β = 99.11 (2)°	T = 293 K
V = 1709.0 (9) Å³	Prism, colourless
Z = 4	0.34 × 0.23 × 0.23 mm

Data collection top

MAR345 image-plate diffractometer	4896 reflections with I > 2σ(I)
Radiation source: RU200 rotating anode	R_int = 0.056
Graphite monochromator	θ_max = 24.4°, θ_min = 2.8°
Detector resolution: 6.66 pixels mm^-1	h = −7→7
222 images, 150mm, ΔΦ 2° scans	k = −34→34
19313 measured reflections	l = −9→9
5448 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: H atoms were placed at standard calculated positions, except H(N1A) and H(N1B) which were obtained from difference map.
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.053	w = 1/[σ²(F_o²) + (0.1033P)² + 0.0697P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.150	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.23 e Å⁻³
5448 reflections	Δρ_min = −0.20 e Å⁻³
414 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.171 (12)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.3 (12)

Crystal data top

C₁₉H₂₅NO₂	V = 1709.0 (9) Å³
M_r = 299.40	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 6.879 (2) Å	µ = 0.08 mm⁻¹
b = 29.563 (9) Å	T = 293 K
c = 8.511 (3) Å	0.34 × 0.23 × 0.23 mm
β = 99.11 (2)°

Data collection top

MAR345 image-plate diffractometer	4896 reflections with I > 2σ(I)
19313 measured reflections	R_int = 0.056
5448 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.150	Δρ_max = 0.23 e Å⁻³
S = 1.06	Δρ_min = −0.20 e Å⁻³
5448 reflections	Absolute structure: Flack (1983)
414 parameters	Absolute structure parameter: −0.3 (12)
1 restraint

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

	x	y	z	U_iso*/U_eq
C1A	0.8795 (5)	0.29334 (14)	−0.1585 (5)	0.1109 (12)
H1A	0.8928	0.2687	−0.2297	0.166*
H2A	0.9727	0.2897	−0.0627	0.166*
H3A	0.9041	0.3214	−0.2085	0.166*
C2A	0.6323 (4)	0.32952 (10)	−0.0339 (4)	0.0745 (7)
C3A	0.7437 (4)	0.36648 (9)	0.0083 (3)	0.0701 (7)
H4A	0.8683	0.3689	−0.0202	0.084*
C4A	0.6700 (3)	0.40182 (8)	0.0966 (3)	0.0602 (6)
C5A	0.7811 (4)	0.44039 (8)	0.1465 (4)	0.0686 (7)
H5A	0.9092	0.4428	0.1252	0.082*
C6A	0.7054 (3)	0.47402 (8)	0.2247 (3)	0.0647 (6)
H6A	0.7832	0.4992	0.2559	0.078*
C7A	0.5091 (3)	0.47253 (7)	0.2618 (3)	0.0542 (5)
C8A	0.4036 (3)	0.43429 (8)	0.2198 (3)	0.0603 (6)
H7A	0.2776	0.4318	0.2456	0.072*
C9A	0.4796 (3)	0.39770 (8)	0.1373 (3)	0.0584 (5)
C10A	0.3681 (4)	0.35861 (9)	0.0933 (4)	0.0753 (7)
H8A	0.2432	0.3556	0.1208	0.090*
C11A	0.4427 (4)	0.32486 (10)	0.0100 (4)	0.0833 (8)
H9A	0.3690	0.2989	−0.0178	0.100*
C12A	0.4351 (3)	0.51331 (7)	0.3417 (3)	0.0525 (5)
H10A	0.5196	0.5177	0.4446	0.063*
C13A	0.2219 (4)	0.50999 (10)	0.3707 (4)	0.0720 (7)
H11A	0.1909	0.5358	0.4304	0.108*
H12A	0.2054	0.4829	0.4295	0.108*
H13A	0.1354	0.5091	0.2705	0.108*
C14A	0.4558 (3)	0.55512 (7)	0.2372 (2)	0.0493 (5)
C15A	0.6693 (4)	0.62180 (9)	0.2099 (3)	0.0652 (6)
H14A	0.5949	0.6220	0.1018	0.078*
C16A	0.8890 (4)	0.61429 (12)	0.1984 (4)	0.0835 (8)
H15A	0.9310	0.6366	0.1289	0.125*
H16A	0.9062	0.5846	0.1569	0.125*
H17A	0.9662	0.6170	0.3023	0.125*
C17A	0.6288 (5)	0.66553 (10)	0.2901 (4)	0.0791 (8)
H18A	0.6953	0.6644	0.4008	0.095*
C18A	0.4108 (5)	0.67128 (12)	0.2905 (4)	0.0937 (9)
H19A	0.3900	0.6947	0.3643	0.141*
H20A	0.3566	0.6434	0.3218	0.141*
H21A	0.3471	0.6794	0.1857	0.141*
C19A	0.7125 (9)	0.70641 (13)	0.2068 (7)	0.146 (2)
H22A	0.7822	0.6955	0.1251	0.219*
H23A	0.8008	0.7233	0.2837	0.219*
H24A	0.6061	0.7256	0.1602	0.219*
N1A	0.6015 (3)	0.58300 (7)	0.2959 (2)	0.0600 (5)
H25A	0.674 (4)	0.5749 (9)	0.399 (3)	0.072*
O1A	0.6865 (3)	0.29359 (8)	−0.1209 (3)	0.0926 (6)
O2A	0.3479 (2)	0.56055 (6)	0.10909 (18)	0.0638 (4)
C1B	1.4133 (5)	0.28841 (11)	0.4488 (5)	0.0954 (10)
H1B	1.4852	0.3128	0.4108	0.143*
H2B	1.4403	0.2609	0.3964	0.143*
H3B	1.4529	0.2851	0.5615	0.143*
C2B	1.1441 (4)	0.33587 (8)	0.4836 (3)	0.0624 (6)
C3B	1.2575 (3)	0.36409 (8)	0.5873 (3)	0.0612 (6)
H4B	1.3906	0.3578	0.6180	0.073*
C4B	1.1744 (3)	0.40273 (7)	0.6484 (3)	0.0548 (5)
C5B	1.2848 (3)	0.43316 (8)	0.7546 (3)	0.0630 (6)
H5B	1.4183	0.4278	0.7871	0.076*
C6B	1.2012 (3)	0.47019 (7)	0.8109 (3)	0.0578 (6)
H6B	1.2784	0.4892	0.8821	0.069*
C7B	0.9991 (3)	0.48051 (7)	0.7637 (3)	0.0497 (5)
C8B	0.8885 (3)	0.45100 (7)	0.6601 (3)	0.0525 (5)
H7B	0.7554	0.4570	0.6281	0.063*
C9B	0.9706 (3)	0.41237 (7)	0.6015 (3)	0.0518 (5)
C10B	0.8583 (3)	0.38165 (8)	0.4936 (3)	0.0628 (6)
H8B	0.7245	0.3870	0.4619	0.075*
C11B	0.9417 (4)	0.34519 (8)	0.4366 (3)	0.0664 (6)
H9B	0.8652	0.3259	0.3656	0.080*
C12B	0.9178 (3)	0.52326 (7)	0.8281 (3)	0.0517 (5)
H10B	0.9860	0.5280	0.9369	0.062*
C13B	0.6956 (3)	0.52122 (9)	0.8328 (3)	0.0636 (6)
H11B	0.6568	0.5475	0.8865	0.095*
H12B	0.6663	0.4945	0.8888	0.095*
H13B	0.6249	0.5204	0.7262	0.095*
C14B	0.9612 (3)	0.56364 (7)	0.7280 (2)	0.0497 (5)
C15B	1.1743 (3)	0.63025 (8)	0.7141 (3)	0.0586 (6)
H14B	1.1059	0.6309	0.6040	0.070*
C16B	1.3948 (4)	0.62548 (13)	0.7123 (5)	0.0938 (10)
H15B	1.4360	0.6479	0.6428	0.141*
H16B	1.4220	0.5959	0.6750	0.141*
H17B	1.4652	0.6297	0.8180	0.141*
C17B	1.1237 (5)	0.67353 (10)	0.7980 (4)	0.0821 (8)
H18B	1.1815	0.6712	0.9106	0.098*
C18B	0.9055 (5)	0.67922 (13)	0.7879 (5)	0.1041 (11)
H19B	0.8790	0.7043	0.8531	0.156*
H20B	0.8501	0.6522	0.8247	0.156*
H21B	0.8477	0.6849	0.6795	0.156*
C19B	1.2091 (9)	0.71554 (14)	0.7288 (8)	0.154 (2)
H22B	1.3500	0.7133	0.7436	0.232*
H23B	1.1720	0.7420	0.7822	0.232*
H24B	1.1587	0.7177	0.6172	0.232*
N1B	1.1086 (3)	0.59047 (7)	0.7934 (2)	0.0571 (5)
H25B	1.181 (4)	0.5859 (10)	0.901 (3)	0.069*
O1B	1.2087 (3)	0.29784 (6)	0.4159 (3)	0.0818 (6)
O2B	0.8661 (2)	0.57009 (6)	0.59501 (19)	0.0678 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1A	0.102 (2)	0.096 (2)	0.141 (3)	0.0166 (19)	0.040 (2)	−0.026 (2)
C2A	0.0831 (18)	0.0627 (15)	0.0750 (16)	0.0152 (13)	0.0040 (13)	−0.0093 (13)
C3A	0.0661 (15)	0.0690 (16)	0.0719 (15)	0.0096 (12)	0.0004 (12)	0.0032 (13)
C4A	0.0557 (12)	0.0604 (13)	0.0622 (13)	0.0013 (10)	0.0024 (11)	0.0086 (11)
C5A	0.0528 (12)	0.0613 (15)	0.0912 (18)	−0.0034 (10)	0.0104 (12)	0.0056 (13)
C6A	0.0541 (12)	0.0568 (13)	0.0828 (17)	−0.0010 (10)	0.0095 (12)	0.0047 (12)
C7A	0.0526 (12)	0.0531 (12)	0.0523 (11)	−0.0008 (9)	−0.0060 (10)	0.0100 (9)
C8A	0.0551 (12)	0.0609 (13)	0.0628 (13)	−0.0030 (10)	0.0033 (10)	0.0006 (10)
C9A	0.0519 (12)	0.0584 (12)	0.0608 (13)	−0.0036 (10)	−0.0031 (10)	0.0057 (10)
C10A	0.0630 (13)	0.0676 (16)	0.0964 (19)	−0.0113 (12)	0.0161 (13)	−0.0088 (14)
C11A	0.0782 (17)	0.0692 (16)	0.102 (2)	−0.0086 (14)	0.0118 (16)	−0.0149 (16)
C12A	0.0539 (11)	0.0543 (12)	0.0466 (11)	−0.0011 (9)	−0.0003 (9)	0.0056 (9)
C13A	0.0644 (14)	0.0712 (16)	0.0836 (18)	−0.0001 (12)	0.0216 (13)	0.0053 (13)
C14A	0.0510 (10)	0.0512 (11)	0.0430 (10)	−0.0011 (9)	−0.0014 (9)	0.0001 (9)
C15A	0.0773 (15)	0.0624 (14)	0.0532 (13)	−0.0123 (11)	0.0021 (11)	0.0047 (11)
C16A	0.0720 (17)	0.093 (2)	0.089 (2)	0.0003 (14)	0.0225 (15)	0.0143 (16)
C17A	0.097 (2)	0.0628 (16)	0.0795 (18)	−0.0071 (14)	0.0197 (16)	0.0009 (13)
C18A	0.098 (2)	0.091 (2)	0.094 (2)	0.0227 (17)	0.0226 (18)	−0.0009 (17)
C19A	0.207 (5)	0.066 (2)	0.188 (5)	−0.030 (3)	0.102 (4)	−0.003 (3)
N1A	0.0698 (12)	0.0565 (11)	0.0477 (10)	−0.0121 (8)	−0.0087 (9)	0.0075 (8)
O1A	0.0889 (13)	0.0792 (13)	0.1099 (16)	0.0081 (10)	0.0166 (12)	−0.0271 (12)
O2A	0.0665 (9)	0.0660 (10)	0.0516 (9)	−0.0051 (7)	−0.0133 (7)	0.0052 (7)
C1B	0.090 (2)	0.080 (2)	0.119 (3)	0.0225 (16)	0.0235 (19)	−0.0139 (18)
C2B	0.0693 (14)	0.0507 (13)	0.0682 (14)	0.0009 (11)	0.0143 (12)	−0.0027 (11)
C3B	0.0554 (12)	0.0552 (13)	0.0726 (14)	0.0032 (10)	0.0085 (11)	0.0032 (11)
C4B	0.0544 (12)	0.0496 (12)	0.0580 (12)	0.0011 (9)	0.0018 (10)	0.0063 (9)
C5B	0.0478 (11)	0.0650 (14)	0.0714 (14)	0.0005 (10)	−0.0058 (10)	−0.0020 (11)
C6B	0.0520 (12)	0.0547 (13)	0.0617 (13)	−0.0021 (10)	−0.0067 (10)	−0.0037 (10)
C7B	0.0524 (11)	0.0494 (11)	0.0443 (10)	0.0008 (9)	−0.0022 (9)	0.0040 (8)
C8B	0.0474 (10)	0.0497 (12)	0.0569 (13)	−0.0018 (8)	−0.0018 (9)	0.0008 (9)
C9B	0.0508 (11)	0.0472 (11)	0.0545 (12)	−0.0043 (9)	−0.0002 (9)	0.0025 (9)
C10B	0.0581 (12)	0.0560 (13)	0.0703 (15)	−0.0016 (10)	−0.0024 (11)	−0.0058 (10)
C11B	0.0691 (14)	0.0555 (13)	0.0705 (15)	−0.0037 (11)	−0.0009 (12)	−0.0097 (11)
C12B	0.0564 (12)	0.0526 (12)	0.0439 (11)	0.0017 (9)	0.0012 (9)	0.0017 (9)
C13B	0.0601 (13)	0.0700 (15)	0.0611 (14)	0.0027 (11)	0.0113 (11)	−0.0018 (11)
C14B	0.0548 (11)	0.0494 (11)	0.0422 (10)	0.0040 (9)	−0.0007 (9)	0.0004 (9)
C15B	0.0559 (12)	0.0592 (13)	0.0581 (13)	−0.0056 (10)	0.0010 (10)	0.0106 (10)
C16B	0.0634 (16)	0.118 (3)	0.101 (2)	0.0088 (15)	0.0161 (16)	0.031 (2)
C17B	0.0913 (19)	0.0650 (16)	0.091 (2)	−0.0090 (14)	0.0195 (16)	0.0063 (14)
C18B	0.105 (2)	0.098 (2)	0.116 (3)	0.0285 (19)	0.038 (2)	0.009 (2)
C19B	0.180 (5)	0.073 (2)	0.230 (6)	−0.023 (3)	0.095 (5)	0.011 (3)
N1B	0.0612 (11)	0.0544 (11)	0.0515 (11)	−0.0049 (8)	−0.0044 (9)	0.0073 (8)
O1B	0.0772 (12)	0.0615 (11)	0.1081 (16)	0.0038 (9)	0.0194 (11)	−0.0196 (10)
O2B	0.0766 (10)	0.0682 (11)	0.0503 (9)	−0.0081 (8)	−0.0156 (8)	0.0074 (7)

Geometric parameters (Å, º) top

C1A—O1A	1.414 (4)	C1B—O1B	1.418 (3)
C1A—H1A	0.9600	C1B—H1B	0.9600
C1A—H2A	0.9600	C1B—H2B	0.9600
C1A—H3A	0.9600	C1B—H3B	0.9600
C2A—C3A	1.350 (4)	C2B—C3B	1.366 (3)
C2A—O1A	1.380 (3)	C2B—O1B	1.369 (3)
C2A—C11A	1.419 (4)	C2B—C11B	1.414 (3)
C3A—C4A	1.426 (4)	C3B—C4B	1.413 (3)
C3A—H4A	0.9300	C3B—H4B	0.9300
C4A—C5A	1.401 (4)	C4B—C5B	1.409 (3)
C4A—C9A	1.411 (3)	C4B—C9B	1.424 (3)
C5A—C6A	1.346 (4)	C5B—C6B	1.359 (3)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—C7A	1.435 (3)	C6B—C7B	1.417 (3)
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—C8A	1.360 (3)	C7B—C8B	1.381 (3)
C7A—C12A	1.511 (3)	C7B—C12B	1.519 (3)
C8A—C9A	1.433 (3)	C8B—C9B	1.400 (3)
C8A—H7A	0.9300	C8B—H7B	0.9300
C9A—C10A	1.405 (3)	C9B—C10B	1.429 (3)
C10A—C11A	1.370 (4)	C10B—C11B	1.347 (3)
C10A—H8A	0.9300	C10B—H8B	0.9300
C11A—H9A	0.9300	C11B—H9B	0.9300
C12A—C13A	1.529 (3)	C12B—C14B	1.523 (3)
C12A—C14A	1.543 (3)	C12B—C13B	1.537 (3)
C12A—H10A	0.9800	C12B—H10B	0.9800
C13A—H11A	0.9600	C13B—H11B	0.9600
C13A—H12A	0.9600	C13B—H12B	0.9600
C13A—H13A	0.9600	C13B—H13B	0.9600
C14A—O2A	1.228 (3)	C14B—O2B	1.229 (3)
C14A—N1A	1.332 (3)	C14B—N1B	1.337 (3)
C15A—N1A	1.475 (3)	C15B—N1B	1.463 (3)
C15A—C17A	1.508 (4)	C15B—C16B	1.526 (4)
C15A—C16A	1.546 (4)	C15B—C17B	1.532 (4)
C15A—H14A	0.9800	C15B—H14B	0.9800
C16A—H15A	0.9600	C16B—H15B	0.9600
C16A—H16A	0.9600	C16B—H16B	0.9600
C16A—H17A	0.9600	C16B—H17B	0.9600
C17A—C18A	1.510 (4)	C17B—C18B	1.499 (5)
C17A—C19A	1.557 (5)	C17B—C19B	1.531 (5)
C17A—H18A	0.9800	C17B—H18B	0.9800
C18A—H19A	0.9600	C18B—H19B	0.9600
C18A—H20A	0.9600	C18B—H20B	0.9600
C18A—H21A	0.9600	C18B—H21B	0.9600
C19A—H22A	0.9600	C19B—H22B	0.9600
C19A—H23A	0.9600	C19B—H23B	0.9600
C19A—H24A	0.9600	C19B—H24B	0.9600
N1A—H25A	0.97 (3)	N1B—H25B	0.98 (3)

O1A—C1A—H1A	109.5	O1B—C1B—H1B	109.5
O1A—C1A—H2A	109.5	O1B—C1B—H2B	109.5
H1A—C1A—H2A	109.5	H1B—C1B—H2B	109.5
O1A—C1A—H3A	109.5	O1B—C1B—H3B	109.5
H1A—C1A—H3A	109.5	H1B—C1B—H3B	109.5
H2A—C1A—H3A	109.5	H2B—C1B—H3B	109.5
C3A—C2A—O1A	125.1 (3)	C3B—C2B—O1B	125.7 (2)
C3A—C2A—C11A	121.0 (2)	C3B—C2B—C11B	120.0 (2)
O1A—C2A—C11A	113.9 (3)	O1B—C2B—C11B	114.3 (2)
C2A—C3A—C4A	119.9 (2)	C2B—C3B—C4B	120.5 (2)
C2A—C3A—H4A	120.0	C2B—C3B—H4B	119.7
C4A—C3A—H4A	120.0	C4B—C3B—H4B	119.7
C5A—C4A—C9A	118.6 (2)	C5B—C4B—C3B	122.9 (2)
C5A—C4A—C3A	122.2 (2)	C5B—C4B—C9B	117.3 (2)
C9A—C4A—C3A	119.1 (2)	C3B—C4B—C9B	119.8 (2)
C6A—C5A—C4A	121.0 (2)	C6B—C5B—C4B	121.7 (2)
C6A—C5A—H5A	119.5	C6B—C5B—H5B	119.2
C4A—C5A—H5A	119.5	C4B—C5B—H5B	119.2
C5A—C6A—C7A	122.5 (2)	C5B—C6B—C7B	121.6 (2)
C5A—C6A—H6A	118.8	C5B—C6B—H6B	119.2
C7A—C6A—H6A	118.8	C7B—C6B—H6B	119.2
C8A—C7A—C6A	116.7 (2)	C8B—C7B—C6B	117.48 (19)
C8A—C7A—C12A	125.3 (2)	C8B—C7B—C12B	123.98 (19)
C6A—C7A—C12A	118.04 (19)	C6B—C7B—C12B	118.53 (19)
C7A—C8A—C9A	122.3 (2)	C7B—C8B—C9B	122.02 (19)
C7A—C8A—H7A	118.8	C7B—C8B—H7B	119.0
C9A—C8A—H7A	118.8	C9B—C8B—H7B	119.0
C10A—C9A—C4A	119.6 (2)	C8B—C9B—C4B	119.88 (19)
C10A—C9A—C8A	121.7 (2)	C8B—C9B—C10B	122.65 (19)
C4A—C9A—C8A	118.7 (2)	C4B—C9B—C10B	117.5 (2)
C11A—C10A—C9A	120.2 (2)	C11B—C10B—C9B	121.5 (2)
C11A—C10A—H8A	119.9	C11B—C10B—H8B	119.3
C9A—C10A—H8A	119.9	C9B—C10B—H8B	119.3
C10A—C11A—C2A	120.0 (3)	C10B—C11B—C2B	120.7 (2)
C10A—C11A—H9A	120.0	C10B—C11B—H9B	119.6
C2A—C11A—H9A	120.0	C2B—C11B—H9B	119.6
C7A—C12A—C13A	114.94 (19)	C7B—C12B—C14B	109.53 (16)
C7A—C12A—C14A	108.13 (16)	C7B—C12B—C13B	113.68 (19)
C13A—C12A—C14A	108.85 (18)	C14B—C12B—C13B	109.24 (18)
C7A—C12A—H10A	108.2	C7B—C12B—H10B	108.1
C13A—C12A—H10A	108.2	C14B—C12B—H10B	108.1
C14A—C12A—H10A	108.2	C13B—C12B—H10B	108.1
C12A—C13A—H11A	109.5	C12B—C13B—H11B	109.5
C12A—C13A—H12A	109.5	C12B—C13B—H12B	109.5
H11A—C13A—H12A	109.5	H11B—C13B—H12B	109.5
C12A—C13A—H13A	109.5	C12B—C13B—H13B	109.5
H11A—C13A—H13A	109.5	H11B—C13B—H13B	109.5
H12A—C13A—H13A	109.5	H12B—C13B—H13B	109.5
O2A—C14A—N1A	124.4 (2)	O2B—C14B—N1B	123.3 (2)
O2A—C14A—C12A	121.23 (18)	O2B—C14B—C12B	120.89 (18)
N1A—C14A—C12A	114.33 (18)	N1B—C14B—C12B	115.77 (18)
N1A—C15A—C17A	110.3 (2)	N1B—C15B—C16B	108.1 (2)
N1A—C15A—C16A	108.0 (2)	N1B—C15B—C17B	110.27 (19)
C17A—C15A—C16A	113.8 (2)	C16B—C15B—C17B	112.4 (2)
N1A—C15A—H14A	108.2	N1B—C15B—H14B	108.7
C17A—C15A—H14A	108.2	C16B—C15B—H14B	108.7
C16A—C15A—H14A	108.2	C17B—C15B—H14B	108.7
C15A—C16A—H15A	109.5	C15B—C16B—H15B	109.5
C15A—C16A—H16A	109.5	C15B—C16B—H16B	109.5
H15A—C16A—H16A	109.5	H15B—C16B—H16B	109.5
C15A—C16A—H17A	109.5	C15B—C16B—H17B	109.5
H15A—C16A—H17A	109.5	H15B—C16B—H17B	109.5
H16A—C16A—H17A	109.5	H16B—C16B—H17B	109.5
C15A—C17A—C18A	110.6 (3)	C18B—C17B—C19B	109.2 (3)
C15A—C17A—C19A	110.6 (3)	C18B—C17B—C15B	111.5 (3)
C18A—C17A—C19A	110.6 (3)	C19B—C17B—C15B	111.6 (3)
C15A—C17A—H18A	108.3	C18B—C17B—H18B	108.1
C18A—C17A—H18A	108.3	C19B—C17B—H18B	108.1
C19A—C17A—H18A	108.3	C15B—C17B—H18B	108.1
C17A—C18A—H19A	109.5	C17B—C18B—H19B	109.5
C17A—C18A—H20A	109.5	C17B—C18B—H20B	109.5
H19A—C18A—H20A	109.5	H19B—C18B—H20B	109.5
C17A—C18A—H21A	109.5	C17B—C18B—H21B	109.5
H19A—C18A—H21A	109.5	H19B—C18B—H21B	109.5
H20A—C18A—H21A	109.5	H20B—C18B—H21B	109.5
C17A—C19A—H22A	109.5	C17B—C19B—H22B	109.5
C17A—C19A—H23A	109.5	C17B—C19B—H23B	109.5
H22A—C19A—H23A	109.5	H22B—C19B—H23B	109.5
C17A—C19A—H24A	109.5	C17B—C19B—H24B	109.5
H22A—C19A—H24A	109.5	H22B—C19B—H24B	109.5
H23A—C19A—H24A	109.5	H23B—C19B—H24B	109.5
C14A—N1A—C15A	124.98 (19)	C14B—N1B—C15B	123.64 (19)
C14A—N1A—H25A	115.8 (16)	C14B—N1B—H25B	123.2 (16)
C15A—N1A—H25A	119.0 (16)	C15B—N1B—H25B	113.2 (16)
C2A—O1A—C1A	118.0 (3)	C2B—O1B—C1B	117.2 (2)

O1A—C2A—C3A—C4A	179.0 (2)	O1B—C2B—C3B—C4B	179.3 (2)
C11A—C2A—C3A—C4A	−0.8 (4)	C11B—C2B—C3B—C4B	0.0 (4)
C2A—C3A—C4A—C5A	178.5 (3)	C2B—C3B—C4B—C5B	−179.5 (2)
C2A—C3A—C4A—C9A	−0.7 (4)	C2B—C3B—C4B—C9B	0.0 (3)
C9A—C4A—C5A—C6A	−3.3 (4)	C3B—C4B—C5B—C6B	179.7 (2)
C3A—C4A—C5A—C6A	177.6 (2)	C9B—C4B—C5B—C6B	0.2 (4)
C4A—C5A—C6A—C7A	0.1 (4)	C4B—C5B—C6B—C7B	−1.0 (4)
C5A—C6A—C7A—C8A	2.7 (3)	C5B—C6B—C7B—C8B	1.1 (3)
C5A—C6A—C7A—C12A	−176.6 (2)	C5B—C6B—C7B—C12B	−178.2 (2)
C6A—C7A—C8A—C9A	−2.3 (3)	C6B—C7B—C8B—C9B	−0.5 (3)
C12A—C7A—C8A—C9A	176.9 (2)	C12B—C7B—C8B—C9B	178.81 (19)
C5A—C4A—C9A—C10A	−177.8 (3)	C7B—C8B—C9B—C4B	−0.3 (3)
C3A—C4A—C9A—C10A	1.4 (3)	C7B—C8B—C9B—C10B	−179.7 (2)
C5A—C4A—C9A—C8A	3.5 (3)	C5B—C4B—C9B—C8B	0.4 (3)
C3A—C4A—C9A—C8A	−177.3 (2)	C3B—C4B—C9B—C8B	−179.1 (2)
C7A—C8A—C9A—C10A	−179.4 (3)	C5B—C4B—C9B—C10B	179.9 (2)
C7A—C8A—C9A—C4A	−0.7 (3)	C3B—C4B—C9B—C10B	0.4 (3)
C4A—C9A—C10A—C11A	−0.7 (4)	C8B—C9B—C10B—C11B	178.7 (2)
C8A—C9A—C10A—C11A	177.9 (3)	C4B—C9B—C10B—C11B	−0.7 (4)
C9A—C10A—C11A—C2A	−0.8 (5)	C9B—C10B—C11B—C2B	0.7 (4)
C3A—C2A—C11A—C10A	1.5 (5)	C3B—C2B—C11B—C10B	−0.3 (4)
O1A—C2A—C11A—C10A	−178.3 (3)	O1B—C2B—C11B—C10B	−179.8 (2)
C8A—C7A—C12A—C13A	−1.7 (3)	C8B—C7B—C12B—C14B	−96.5 (2)
C6A—C7A—C12A—C13A	177.4 (2)	C6B—C7B—C12B—C14B	82.8 (2)
C8A—C7A—C12A—C14A	−123.6 (2)	C8B—C7B—C12B—C13B	26.0 (3)
C6A—C7A—C12A—C14A	55.6 (2)	C6B—C7B—C12B—C13B	−154.6 (2)
C7A—C12A—C14A—O2A	71.6 (2)	C7B—C12B—C14B—O2B	75.6 (2)
C13A—C12A—C14A—O2A	−53.9 (3)	C13B—C12B—C14B—O2B	−49.5 (3)
C7A—C12A—C14A—N1A	−106.6 (2)	C7B—C12B—C14B—N1B	−103.6 (2)
C13A—C12A—C14A—N1A	127.9 (2)	C13B—C12B—C14B—N1B	131.2 (2)
N1A—C15A—C17A—C18A	−60.8 (3)	N1B—C15B—C17B—C18B	−63.5 (3)
C16A—C15A—C17A—C18A	177.6 (3)	C16B—C15B—C17B—C18B	175.8 (3)
N1A—C15A—C17A—C19A	176.2 (3)	N1B—C15B—C17B—C19B	174.1 (3)
C16A—C15A—C17A—C19A	54.7 (4)	C16B—C15B—C17B—C19B	53.4 (4)
O2A—C14A—N1A—C15A	−6.8 (4)	O2B—C14B—N1B—C15B	−0.5 (3)
C12A—C14A—N1A—C15A	171.3 (2)	C12B—C14B—N1B—C15B	178.7 (2)
C17A—C15A—N1A—C14A	114.6 (3)	C16B—C15B—N1B—C14B	−125.4 (3)
C16A—C15A—N1A—C14A	−120.5 (3)	C17B—C15B—N1B—C14B	111.4 (3)
C3A—C2A—O1A—C1A	5.5 (5)	C3B—C2B—O1B—C1B	−4.0 (4)
C11A—C2A—O1A—C1A	−174.7 (3)	C11B—C2B—O1B—C1B	175.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H25A···O2B	0.97 (3)	1.96 (3)	2.911 (3)	166 (2)
N1B—H25B···O2Aⁱ	0.98 (3)	2.09 (3)	3.051 (3)	166 (2)

Symmetry code: (i) x+1, y, z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₅NO₂
M_r	299.40
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	6.879 (2), 29.563 (9), 8.511 (3)
β (°)	99.11 (2)
V (Å³)	1709.0 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.34 × 0.23 × 0.23

Data collection
Diffractometer	MAR345 image-plate diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	19313, 5448, 4896
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.581

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.150, 1.06
No. of reflections	5448
No. of parameters	414
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.20
Absolute structure	Flack (1983)
Absolute structure parameter	−0.3 (12)

Computer programs: marHKL (Klein & Bartels, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), SHELXL97.

Selected geometric parameters (Å, º) top

C1A—O1A	1.414 (4)	C1B—O1B	1.418 (3)
C2A—O1A	1.380 (3)	C2B—O1B	1.369 (3)
C14A—O2A	1.228 (3)	C14B—O2B	1.229 (3)
C14A—N1A	1.332 (3)	C14B—N1B	1.337 (3)
C15A—N1A	1.475 (3)	C15B—N1B	1.463 (3)

O2A—C14A—N1A	124.4 (2)	O2B—C14B—N1B	123.3 (2)
O2A—C14A—C12A	121.23 (18)	O2B—C14B—C12B	120.89 (18)
N1A—C14A—C12A	114.33 (18)	N1B—C14B—C12B	115.77 (18)
C2A—O1A—C1A	118.0 (3)	C2B—O1B—C1B	117.2 (2)

C7A—C12A—C14A—O2A	71.6 (2)	C7B—C12B—C14B—O2B	75.6 (2)
C7A—C12A—C14A—N1A	−106.6 (2)	C7B—C12B—C14B—N1B	−103.6 (2)
C12A—C14A—N1A—C15A	171.3 (2)	C12B—C14B—N1B—C15B	178.7 (2)
C17A—C15A—N1A—C14A	114.6 (3)	C16B—C15B—N1B—C14B	−125.4 (3)
C16A—C15A—N1A—C14A	−120.5 (3)	C17B—C15B—N1B—C14B	111.4 (3)
C3A—C2A—O1A—C1A	5.5 (5)	C3B—C2B—O1B—C1B	−4.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H25A···O2B	0.97 (3)	1.96 (3)	2.911 (3)	166 (2)
N1B—H25B···O2Aⁱ	0.98 (3)	2.09 (3)	3.051 (3)	166 (2)

Symmetry code: (i) x+1, y, z+1.

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