The title compound, C
8H
12N
+·C
14H
13O
3−, is the less soluble diastereomeric salt of 2-hydroxymethyl-2-(2-naphthyl)propanoic acid with (
R)-(+)-phenylethylamine. The ammonium group of the cation and the carboxylate group of the anion are linked
via N—H
O hydrogen bonds, forming ribbons along the
b axis.
Supporting information
CCDC reference: 272046
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.011 Å
- Disorder in main residue
- R factor = 0.048
- wR factor = 0.102
- Data-to-parameter ratio = 7.6
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 38 Perc.
PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size ....... 0.90 mm
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 11
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.60
PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C14 H13 O3
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 25.00
From the CIF: _reflns_number_total 1854
Count of symmetry unique reflns 1857
Completeness (_total/calc) 99.84%
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
0 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
6 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
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.
(
R)-1-Phenyl-1-ethylammonium
(
R)-2-hydroxymethyl-2-(2-naphthyl)propanoate
top
Crystal data top
C8H12N+·C14H13O3− | F(000) = 376 |
Mr = 351.44 | Dx = 1.213 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 25 reflections |
a = 12.791 (2) Å | θ = 10.1–11.8° |
b = 6.4448 (16) Å | µ = 0.08 mm−1 |
c = 12.068 (3) Å | T = 298 K |
β = 104.741 (16)° | Needle, colorless |
V = 962.1 (4) Å3 | 0.9 × 0.1 × 0.05 mm |
Z = 2 | |
Data collection top
Rigaku AFC-7R diffractometer | Rint = 0.024 |
ω–2θ scans | θmax = 25.0° |
Absorption correction: integration (ABSCOR; Higashi, 1999) | h = −6→15 |
Tmin = 0.992, Tmax = 0.996 | k = 0→7 |
2165 measured reflections | l = −14→13 |
1854 independent reflections | 3 standard reflections every 150 reflections |
698 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.048 | w = 1/[σ2(Fo2) + (0.0179P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.102 | (Δ/σ)max = 0.016 |
S = 0.97 | Δρmax = 0.16 e Å−3 |
1854 reflections | Δρmin = −0.19 e Å−3 |
244 parameters | Absolute structure: see text |
Special details top
Refinement. Refinement using reflections with F2 > 0.0 σ(F2). The
weighted R-factor (wR), goodness of fit (S) and
R-factor (gt) are based on F, with F set to zero for
negative F. The threshold expression of F2 > 2.0
σ(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.2178 (4) | 0.1328 (8) | 0.0667 (4) | 0.052 (1) | |
O2 | 0.1292 (3) | −0.1683 (7) | 0.0477 (3) | 0.049 (1) | |
O3A | 0.4034 (5) | 0.088 (1) | −0.0053 (6) | 0.082 (3) | 0.70 |
O3B | 0.522 (1) | −0.151 (3) | 0.144 (2) | 0.103 (7) | 0.30 |
N4 | 0.0723 (4) | 0.4311 (8) | 0.0981 (4) | 0.043 (1) | |
C5 | 0.3239 (5) | −0.182 (1) | 0.1008 (6) | 0.042 (2) | |
C6 | 0.2165 (6) | −0.062 (1) | 0.0704 (5) | 0.038 (2) | |
C7 | 0.4176 (5) | −0.030 (1) | 0.1003 (6) | 0.061 (2) | |
C8 | 0.3199 (5) | −0.351 (1) | 0.0109 (6) | 0.063 (2) | |
C9 | 0.3413 (5) | −0.265 (1) | 0.2237 (7) | 0.051 (2) | |
C10 | 0.3167 (5) | −0.142 (1) | 0.3064 (7) | 0.051 (2) | |
C11 | 0.3321 (6) | −0.208 (1) | 0.4203 (7) | 0.058 (2) | |
C12 | 0.3048 (6) | −0.087 (1) | 0.5040 (7) | 0.070 (2) | |
C13 | 0.3165 (6) | −0.155 (2) | 0.6126 (8) | 0.085 (3) | |
C14 | 0.3594 (7) | −0.353 (2) | 0.6449 (7) | 0.086 (3) | |
C15 | 0.3879 (7) | −0.479 (2) | 0.5663 (9) | 0.084 (3) | |
C16 | 0.3742 (6) | −0.411 (1) | 0.4509 (8) | 0.056 (2) | |
C17 | 0.4001 (6) | −0.532 (1) | 0.3665 (9) | 0.070 (3) | |
C18 | 0.3836 (6) | −0.463 (1) | 0.2566 (7) | 0.059 (2) | |
C19 | 0.0365 (7) | 0.181 (1) | 0.2359 (6) | 0.076 (3) | |
C20 | 0.0757 (5) | 0.396 (1) | 0.2216 (6) | 0.051 (2) | |
C21 | 0.0135 (5) | 0.560 (1) | 0.2682 (6) | 0.048 (2) | |
C22 | 0.0582 (5) | 0.643 (1) | 0.3732 (6) | 0.053 (2) | |
C23 | −0.0007 (7) | 0.777 (1) | 0.4241 (6) | 0.063 (2) | |
C24 | −0.1056 (7) | 0.826 (1) | 0.3710 (6) | 0.067 (2) | |
C25 | −0.1506 (6) | 0.745 (1) | 0.2639 (7) | 0.078 (3) | |
C26 | −0.0922 (6) | 0.612 (2) | 0.2137 (6) | 0.071 (2) | |
H3A | 0.3381 | 0.1653 | −0.0189 | 0.0978* | 0.70 |
H3B | 0.5263 | −0.2562 | 0.0899 | 0.1231* | 0.30 |
H4A | 0.1214 | 0.3393 | 0.0758 | 0.0517* | |
H4B | 0.0012 | 0.4060 | 0.0524 | 0.0517* | |
H4C | 0.0922 | 0.5704 | 0.0878 | 0.0517* | |
H7A1 | 0.4826 | −0.1078 | 0.1119 | 0.0729* | 0.70 |
H7A2 | 0.4235 | 0.0651 | 0.1618 | 0.0729* | 0.70 |
H7B1 | 0.4155 | 0.0844 | 0.1494 | 0.0729* | 0.30 |
H7B2 | 0.4121 | 0.0190 | 0.0248 | 0.0729* | 0.30 |
H8A | 0.2614 | −0.4421 | 0.0099 | 0.0757* | |
H8B | 0.3100 | −0.2882 | −0.0624 | 0.0757* | |
H8C | 0.3858 | −0.4264 | 0.0291 | 0.0757* | |
H10 | 0.2882 | −0.0071 | 0.2858 | 0.0609* | |
H12 | 0.2770 | 0.0485 | 0.4844 | 0.0836* | |
H13 | 0.2955 | −0.0690 | 0.6671 | 0.1022* | |
H14 | 0.3687 | −0.3988 | 0.7216 | 0.1028* | |
H15 | 0.4169 | −0.6128 | 0.5886 | 0.1009* | |
H17 | 0.4300 | −0.6664 | 0.3858 | 0.0842* | |
H18 | 0.4011 | −0.5512 | 0.2008 | 0.0707* | |
H19A | −0.0362 | 0.1668 | 0.1920 | 0.0915* | |
H19B | 0.0806 | 0.0829 | 0.2104 | 0.0915* | |
H19C | 0.0401 | 0.1569 | 0.3145 | 0.0915* | |
H20 | 0.1492 | 0.4039 | 0.2641 | 0.0615* | |
H22 | 0.1304 | 0.6087 | 0.4122 | 0.0639* | |
H23 | 0.0323 | 0.8361 | 0.4967 | 0.0759* | |
H24 | −0.1464 | 0.9142 | 0.4072 | 0.0809* | |
H25 | −0.2224 | 0.7818 | 0.2244 | 0.0939* | |
H26 | −0.1249 | 0.5542 | 0.1406 | 0.0847* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.052 (3) | 0.034 (3) | 0.070 (4) | 0.004 (3) | 0.015 (2) | 0.006 (3) |
O2 | 0.033 (3) | 0.044 (3) | 0.065 (3) | −0.005 (3) | 0.004 (2) | 0.005 (3) |
O3A | 0.046 (4) | 0.091 (7) | 0.115 (6) | −0.012 (5) | 0.034 (4) | 0.028 (6) |
O3B | 0.07 (1) | 0.09 (2) | 0.15 (2) | −0.03 (1) | 0.04 (1) | −0.04 (2) |
N4 | 0.039 (3) | 0.032 (4) | 0.061 (4) | 0.003 (3) | 0.017 (3) | 0.002 (4) |
C5 | 0.032 (4) | 0.038 (5) | 0.062 (5) | 0.001 (4) | 0.022 (4) | 0.001 (5) |
C6 | 0.043 (5) | 0.042 (5) | 0.032 (4) | 0.016 (5) | 0.014 (4) | 0.001 (5) |
C7 | 0.045 (5) | 0.050 (6) | 0.089 (6) | 0.002 (4) | 0.020 (5) | 0.008 (5) |
C8 | 0.061 (5) | 0.050 (5) | 0.082 (6) | 0.003 (5) | 0.025 (4) | −0.013 (5) |
C9 | 0.031 (4) | 0.035 (5) | 0.086 (6) | 0.006 (4) | 0.014 (4) | −0.001 (5) |
C10 | 0.043 (4) | 0.042 (5) | 0.066 (5) | 0.011 (4) | 0.012 (4) | 0.001 (5) |
C11 | 0.040 (4) | 0.064 (7) | 0.068 (7) | −0.015 (5) | 0.013 (4) | −0.015 (6) |
C12 | 0.067 (6) | 0.081 (6) | 0.055 (5) | 0.006 (5) | 0.003 (5) | 0.001 (6) |
C13 | 0.057 (5) | 0.13 (1) | 0.069 (7) | 0.002 (7) | 0.015 (5) | 0.004 (7) |
C14 | 0.059 (6) | 0.124 (10) | 0.067 (7) | −0.004 (7) | 0.004 (5) | 0.044 (8) |
C15 | 0.062 (6) | 0.094 (8) | 0.089 (7) | −0.006 (6) | 0.006 (6) | 0.015 (8) |
C16 | 0.046 (5) | 0.044 (6) | 0.073 (7) | 0.004 (5) | 0.007 (4) | 0.011 (5) |
C17 | 0.057 (5) | 0.045 (6) | 0.097 (7) | 0.009 (5) | −0.001 (6) | 0.011 (6) |
C18 | 0.050 (5) | 0.042 (6) | 0.079 (6) | 0.015 (5) | 0.006 (5) | −0.001 (5) |
C19 | 0.118 (7) | 0.040 (6) | 0.086 (7) | 0.016 (6) | 0.054 (6) | 0.022 (5) |
C20 | 0.050 (4) | 0.056 (6) | 0.048 (5) | 0.007 (4) | 0.013 (4) | 0.009 (5) |
C21 | 0.053 (5) | 0.047 (5) | 0.047 (5) | 0.002 (5) | 0.019 (4) | −0.005 (5) |
C22 | 0.062 (5) | 0.057 (5) | 0.042 (5) | 0.004 (5) | 0.016 (4) | 0.015 (5) |
C23 | 0.081 (6) | 0.059 (6) | 0.053 (5) | −0.004 (5) | 0.023 (5) | −0.003 (5) |
C24 | 0.084 (6) | 0.053 (6) | 0.073 (6) | 0.005 (6) | 0.033 (5) | −0.008 (6) |
C25 | 0.044 (5) | 0.102 (8) | 0.087 (6) | 0.025 (5) | 0.013 (5) | −0.010 (6) |
C26 | 0.046 (5) | 0.092 (7) | 0.064 (5) | 0.007 (5) | −0.003 (4) | −0.023 (6) |
Geometric parameters (Å, º) top
O1—C6 | 1.255 (9) | C12—H12 | 0.950 |
O2—C6 | 1.280 (8) | C13—C14 | 1.40 (2) |
O3A—C7 | 1.46 (1) | C13—H13 | 0.950 |
O3A—H3A | 0.950 | C14—C15 | 1.37 (2) |
O3B—C7 | 1.52 (2) | C14—H14 | 0.950 |
O3B—H3B | 0.950 | C15—C16 | 1.43 (1) |
N4—C20 | 1.497 (9) | C15—H15 | 0.950 |
N4—H4A | 0.950 | C16—C17 | 1.39 (1) |
N4—H4B | 0.950 | C17—C18 | 1.36 (1) |
N4—H4C | 0.950 | C17—H17 | 0.950 |
C5—C6 | 1.539 (9) | C18—H18 | 0.950 |
C5—C7 | 1.551 (10) | C19—C20 | 1.50 (1) |
C5—C8 | 1.53 (1) | C19—H19A | 0.950 |
C5—C9 | 1.54 (1) | C19—H19B | 0.950 |
C7—H7A1 | 0.950 | C19—H19C | 0.950 |
C7—H7A2 | 0.950 | C20—C21 | 1.51 (1) |
C7—H7B1 | 0.950 | C20—H20 | 0.950 |
C7—H7B2 | 0.950 | C21—C22 | 1.362 (10) |
C8—H8A | 0.950 | C21—C26 | 1.386 (9) |
C8—H8B | 0.950 | C22—C23 | 1.39 (1) |
C8—H8C | 0.950 | C22—H22 | 0.950 |
C9—C10 | 1.37 (1) | C23—C24 | 1.37 (1) |
C9—C18 | 1.41 (1) | C23—H23 | 0.950 |
C10—C11 | 1.40 (1) | C24—C25 | 1.38 (1) |
C10—H10 | 0.950 | C24—H24 | 0.950 |
C11—C12 | 1.39 (1) | C25—C26 | 1.38 (1) |
C11—C16 | 1.42 (1) | C25—H25 | 0.950 |
C12—C13 | 1.35 (1) | C26—H26 | 0.950 |
| | | |
C7—O3A—H3A | 109.5 | C12—C13—C14 | 120.2 (10) |
C7—O3B—H3B | 109.5 | C12—C13—H13 | 119.9 |
C20—N4—H4A | 109.5 | C14—C13—H13 | 119.9 |
C20—N4—H4B | 109.5 | C13—C14—C15 | 120.1 (9) |
C20—N4—H4C | 109.5 | C13—C14—H14 | 119.9 |
H4A—N4—H4B | 109.5 | C15—C14—H14 | 119.9 |
H4A—N4—H4C | 109.5 | C14—C15—C16 | 120.3 (9) |
H4B—N4—H4C | 109.5 | C14—C15—H15 | 119.9 |
C6—C5—C7 | 108.8 (6) | C16—C15—H15 | 119.9 |
C6—C5—C8 | 108.9 (5) | C11—C16—C15 | 118.7 (9) |
C6—C5—C9 | 107.8 (6) | C11—C16—C17 | 118.1 (8) |
C7—C5—C8 | 109.5 (6) | C15—C16—C17 | 123.2 (8) |
C7—C5—C9 | 107.4 (5) | C16—C17—C18 | 121.4 (7) |
C8—C5—C9 | 114.3 (6) | C16—C17—H17 | 119.3 |
O1—C6—O2 | 123.2 (6) | C18—C17—H17 | 119.3 |
O1—C6—C5 | 119.6 (6) | C9—C18—C17 | 121.7 (8) |
O2—C6—C5 | 117.2 (6) | C9—C18—H18 | 119.1 |
O3A—C7—O3B | 118.2 (10) | C17—C18—H18 | 119.1 |
O3A—C7—C5 | 114.2 (5) | C20—C19—H19A | 109.5 |
O3A—C7—H7A1 | 108.3 | C20—C19—H19B | 109.5 |
O3A—C7—H7A2 | 108.3 | C20—C19—H19C | 109.5 |
O3B—C7—C5 | 106.6 (9) | H19A—C19—H19B | 109.5 |
O3B—C7—H7B1 | 110.2 | H19A—C19—H19C | 109.5 |
O3B—C7—H7B2 | 110.2 | H19B—C19—H19C | 109.5 |
C5—C7—H7A1 | 108.3 | N4—C20—C19 | 109.2 (5) |
C5—C7—H7A2 | 108.3 | N4—C20—C21 | 112.3 (5) |
C5—C7—H7B1 | 110.2 | N4—C20—H20 | 107.6 |
C5—C7—H7B2 | 110.2 | C19—C20—C21 | 112.2 (6) |
H7A1—C7—H7A2 | 109.5 | C19—C20—H20 | 107.6 |
H7B1—C7—H7B2 | 109.5 | C21—C20—H20 | 107.6 |
C5—C8—H8A | 109.5 | C20—C21—C22 | 119.0 (6) |
C5—C8—H8B | 109.5 | C20—C21—C26 | 122.3 (6) |
C5—C8—H8C | 109.5 | C22—C21—C26 | 118.3 (7) |
H8A—C8—H8B | 109.5 | C21—C22—C23 | 120.7 (6) |
H8A—C8—H8C | 109.5 | C21—C22—H22 | 119.6 |
H8B—C8—H8C | 109.5 | C23—C22—H22 | 119.6 |
C5—C9—C10 | 119.9 (6) | C22—C23—C24 | 120.9 (6) |
C5—C9—C18 | 122.5 (7) | C22—C23—H23 | 119.5 |
C10—C9—C18 | 117.6 (8) | C24—C23—H23 | 119.5 |
C9—C10—C11 | 122.4 (7) | C23—C24—C25 | 118.6 (8) |
C9—C10—H10 | 118.8 | C23—C24—H24 | 120.7 |
C11—C10—H10 | 118.8 | C25—C24—H24 | 120.7 |
C10—C11—C12 | 122.8 (8) | C24—C25—C26 | 120.3 (7) |
C10—C11—C16 | 118.8 (8) | C24—C25—H25 | 119.8 |
C12—C11—C16 | 118.3 (8) | C26—C25—H25 | 119.8 |
C11—C12—C13 | 122.3 (9) | C21—C26—C25 | 121.1 (6) |
C11—C12—H12 | 118.8 | C21—C26—H26 | 119.5 |
C13—C12—H12 | 118.8 | C25—C26—H26 | 119.5 |
| | | |
O1—C6—C5—C7 | −10.2 (8) | C10—C11—C12—C13 | 177.6 (7) |
O1—C6—C5—C8 | −129.5 (7) | C10—C11—C16—C15 | −178.8 (7) |
O1—C6—C5—C9 | 106.1 (7) | C10—C11—C16—C17 | 1 (1) |
O2—C6—C5—C7 | 168.4 (6) | C11—C10—C9—C18 | −0.2 (10) |
O2—C6—C5—C8 | 49.1 (8) | C11—C12—C13—C14 | 1 (1) |
O2—C6—C5—C9 | −75.4 (7) | C11—C16—C15—C14 | 0 (1) |
O3A—C7—C5—C6 | −53.8 (8) | C11—C16—C17—C18 | −1 (1) |
O3A—C7—C5—C8 | 65.1 (8) | C12—C11—C16—C15 | 0 (1) |
O3A—C7—C5—C9 | −170.3 (6) | C12—C11—C16—C17 | 179.2 (7) |
O3B—C7—C5—C6 | 173.8 (9) | C12—C13—C14—C15 | −1 (1) |
O3B—C7—C5—C8 | −67.3 (10) | C13—C12—C11—C16 | 0 (1) |
O3B—C7—C5—C9 | 57 (1) | C13—C14—C15—C16 | 0 (1) |
N4—C20—C21—C22 | −136.0 (7) | C14—C15—C16—C17 | −179.1 (8) |
N4—C20—C21—C26 | 51.3 (9) | C15—C16—C17—C18 | 178.5 (7) |
C5—C9—C10—C11 | −179.3 (6) | C19—C20—C21—C22 | 100.5 (8) |
C5—C9—C18—C17 | 178.9 (6) | C19—C20—C21—C26 | −72.2 (9) |
C6—C5—C9—C10 | −40.6 (8) | C20—C21—C22—C23 | −173.3 (7) |
C6—C5—C9—C18 | 140.4 (6) | C20—C21—C26—C25 | 173.2 (8) |
C7—C5—C9—C10 | 76.6 (8) | C21—C22—C23—C24 | 1 (1) |
C7—C5—C9—C18 | −102.4 (7) | C21—C26—C25—C24 | −1 (1) |
C8—C5—C9—C10 | −161.8 (6) | C22—C21—C26—C25 | 0 (1) |
C8—C5—C9—C18 | 19.2 (9) | C22—C23—C24—C25 | −2 (1) |
C9—C10—C11—C12 | −178.2 (7) | C23—C22—C21—C26 | 0 (1) |
C9—C10—C11—C16 | 0 (1) | C23—C24—C25—C26 | 2 (1) |
C9—C18—C17—C16 | 1 (1) | C23—C24—C25—C26 | 2 (1) |
C10—C9—C18—C17 | 0 (1) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3A—H3A···O1 | 0.95 | 2.07 | 2.743 (9) | 126 |
O3B—H3B···O3Ai | 0.95 | 1.82 | 2.71 (2) | 154 |
N4—H4A···O1 | 0.95 | 1.84 | 2.769 (7) | 166 |
N4—H4B···O2ii | 0.95 | 1.86 | 2.801 (6) | 172 |
N4—H4C···O2iii | 0.95 | 1.85 | 2.791 (7) | 172 |
Symmetry codes: (i) −x+1, y−1/2, −z; (ii) −x, y+1/2, −z; (iii) x, y+1, z. |