(R)-1-Phen­yl-1-ethyl­ammonium (R)-2-hydroxy­meth­yl-2-(2-naphth­yl)propanoate

The title compound, C₈H₁₂N⁺·C₁₄H₁₃O₃⁻, 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.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3	0.9 × 0.1 × 0.05 mm
Z = 2

Data collection

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

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.048	w = 1/[σ^2(Fo^2) + (0.0179P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O3A^i	0.95	1.82	2.71 (2)	154
N4—H4A···O1	0.95	1.84	2.769 (7)	166
N4—H4B···O2^ii	0.95	1.86	2.801 (6)	172
N4—H4C···O2^iii	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.