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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.
Supporting information
CCDC reference: 170785
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
The preparation of the title compound is described in Khelili et al.
(1999). Crystals were obtained by slow evaporation of a methanol solution.
H atoms were constrained (included as riding atoms) except for HN1A and HN1B
which were refined, with isotropic displacement parameters fixed at
1.2Ueq of the parent atom (1.5Ueq for methyl atoms).
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.
N-[(
R)-3-methyl-2-butyl]-(
S)-2-(6-methoxy-2-naphthyl)propionamide
top
Crystal data top
C19H25NO2 | F(000) = 648 |
Mr = 299.40 | Dx = 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 | Rint = 0.056 |
Graphite monochromator | θmax = 24.4°, θmin = 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(Fo2) + (0.1033P)2 + 0.0697P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.150 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.23 e Å−3 |
5448 reflections | Δρmin = −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 |
Mr = 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 | Rint = 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 | Δρmax = 0.23 e Å−3 |
S = 1.06 | Δρmin = −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 | Uiso*/Ueq | |
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 |
Mr | 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 |
Rint | 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 |
Δρmax, Δρmin (e Å−3) | 0.23, −0.20 |
Absolute structure | Flack (1983) |
Absolute structure parameter | −0.3 (12) |
Selected geometric parameters (Å, º) topC1A—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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(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.