The absolute configuration of a new amino­alkyl­phenol derived from (R)-(–)-2-phenyl­glycine

The chiral amino­alkyl­phenol N-[(S)-1-(5-methyl-2-hydroxy­phen­yl)eth­yl]-N–[(R)-2-hydr­oxy-1-phenyl­ethyl]amine, C₁₇H₂₁NO₂, was synthesized starting from R-(-)-2-phenyl­glycine. The corresponding hydro­chloride salt was prepared and crystallized as an ethyl acetate solvate, affording N-[(R)-2-hydr­oxy-1-phenyl­ethyl]-N-[(S)-1-(5-methyl-2-hydroxy­phen­yl)eth­yl]aminium chloride ethyl acetate solvate, C₁₇H₂₂NO₂⁺·Cl⁻·C₄H₈O₂, and the absolute configuration of the new stereogenic centre determined, from which that of the chiral amino­alkyl­phenol was inferred. The dihedral angle between the two aromatic rings is 40.74 (11)°.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.052
• wR factor = 0.144
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level B
SYMMS02_ALERT_1_B  The unit-cell lengths a and c should not be equal for a
            monoclinic cell
  Cell      12.0430    7.7441   12.0430
  Angles    90.0000  103.0700   90.0000

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.59 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.25 Ratio
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C19
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.20
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C20    -   C21    ...       1.39 Ang.
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.08

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           25.15
           From the CIF: _reflns_number_total               3672
           Count of symmetry unique reflns         2122
           Completeness (_total/calc)            173.04%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1550
           Fraction of Friedel pairs measured     0.730
           Are heavy atom types Z>Si present        yes

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

(I)

Crystal data

C17H22NO2^+·Cl^−·C4H8O2	F(000) = 424
Mr = 395.91	Dx = 1.202 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2743 reflections
a = 12.043 (2) Å	θ = 2.7–25.9°
b = 7.7441 (16) Å	µ = 0.20 mm^−1
c = 12.043 (2) Å	T = 298 K
β = 103.07 (2)°	Block, colourless
V = 1094.2 (4) Å^3	0.50 × 0.40 × 0.12 mm
Z = 2

Data collection

Bruker SMART diffractometer	3672 independent reflections
Radiation source: fine-focus sealed tube	3546 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 25.2°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→10
Tmin = 0.907, Tmax = 0.977	k = −8→9
5629 measured reflections	l = −14→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.144	w = 1/[σ^2(Fo^2) + (0.0958P)^2 + 0.1694P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
3672 reflections	Δρmax = 0.23 e Å^−3
250 parameters	Δρmin = −0.23 e Å^−3
168 restraints	Absolute structure: Flack (1983), 1550 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (8)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2637 (3)	−0.0013 (5)	0.7310 (3)	0.0566 (9)
H1	0.3309	−0.0010	0.7872	0.068*
C2	0.2609 (4)	−0.0814 (6)	0.6285 (4)	0.0757 (12)
H2	0.3254	−0.1370	0.6159	0.091*
C3	0.1609 (5)	−0.0787 (6)	0.5437 (3)	0.0766 (12)
H3A	0.1592	−0.1292	0.4732	0.092*
C4	0.0663 (4)	−0.0029 (6)	0.5637 (3)	0.0663 (10)
H4A	−0.0007	−0.0037	0.5074	0.080*
C5	0.0681 (3)	0.0758 (5)	0.6668 (3)	0.0508 (7)
H5	0.0023	0.1272	0.6795	0.061*
C6	0.1672 (2)	0.0790 (4)	0.7514 (2)	0.0391 (6)
C7	0.1726 (2)	0.1551 (4)	0.8672 (2)	0.0372 (6)
H7	0.2529	0.1721	0.9048	0.045*
C8	0.1193 (3)	0.0372 (4)	0.9420 (3)	0.0497 (8)
H8A	0.0407	0.0125	0.9049	0.060*
H8B	0.1607	−0.0711	0.9550	0.060*
C9	0.1625 (2)	0.4678 (4)	0.8003 (2)	0.0335 (6)
H9	0.1809	0.4181	0.7318	0.040*
C10	0.0717 (2)	0.6066 (4)	0.7627 (3)	0.0452 (7)
H10A	0.0520	0.6566	0.8286	0.068*
H10B	0.0051	0.5556	0.7149	0.068*
H10C	0.1009	0.6948	0.7210	0.068*
C11	0.2707 (2)	0.5407 (4)	0.8735 (2)	0.0363 (6)
C12	0.3636 (2)	0.5700 (4)	0.8266 (3)	0.0426 (7)
H12	0.3613	0.5303	0.7532	0.051*
C13	0.4603 (3)	0.6567 (5)	0.8852 (3)	0.0540 (8)
C14	0.5599 (3)	0.6900 (7)	0.8299 (4)	0.0865 (15)
H14A	0.5842	0.8079	0.8426	0.130*
H14B	0.5367	0.6687	0.7494	0.130*
H14C	0.6219	0.6145	0.8627	0.130*
C15	0.4619 (3)	0.7109 (5)	0.9941 (3)	0.0596 (9)
H15	0.5254	0.7700	1.0349	0.072*
C16	0.3719 (3)	0.6800 (5)	1.0446 (3)	0.0571 (9)
H16	0.3759	0.7161	1.1191	0.069*
C17	0.2761 (2)	0.5958 (4)	0.9850 (2)	0.0414 (7)
C18	0.2151 (4)	0.3088 (12)	0.3504 (5)	0.115 (2)
H18A	0.1362	0.3288	0.3492	0.172*
H18B	0.2253	0.1914	0.3293	0.172*
H18C	0.2389	0.3853	0.2975	0.172*
C19	0.2845 (5)	0.3413 (10)	0.4665 (5)	0.112 (2)
C20	0.4620 (7)	0.3021 (15)	0.5910 (6)	0.158 (3)
H20A	0.4786	0.4246	0.6000	0.189*
H20B	0.4269	0.2651	0.6520	0.189*
C21	0.5616 (7)	0.209 (2)	0.5941 (7)	0.215 (6)
H21A	0.5501	0.0908	0.6120	0.322*
H21B	0.6224	0.2572	0.6514	0.322*
H21C	0.5809	0.2160	0.5212	0.322*
Cl1	0.84321 (5)	0.30827 (11)	0.78328 (5)	0.0458 (2)
N1	0.11353 (17)	0.3263 (3)	0.86111 (17)	0.0337 (5)
H1A	0.1153	0.3618	0.9326	0.040*
H1B	0.0399	0.3114	0.8257	0.040*
O1	0.2635 (5)	0.4201 (8)	0.5468 (4)	0.155 (2)
O2	0.3851 (3)	0.2682 (8)	0.4793 (3)	0.1270 (16)
O3	0.1831 (2)	0.5626 (4)	1.02948 (19)	0.0572 (6)
H3	0.1828	0.6291	1.0824	0.086*
O4	0.1245 (3)	0.1230 (4)	1.0469 (2)	0.0726 (8)
H4	0.1428	0.0540	1.0995	0.109*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.061 (2)	0.051 (2)	0.061 (2)	0.0024 (16)	0.0211 (16)	−0.0005 (17)
C2	0.099 (3)	0.062 (3)	0.082 (3)	0.011 (2)	0.055 (3)	−0.008 (2)
C3	0.126 (4)	0.063 (3)	0.052 (2)	−0.006 (3)	0.044 (2)	−0.0100 (19)
C4	0.089 (3)	0.065 (3)	0.0407 (16)	−0.003 (2)	0.0072 (17)	−0.0080 (17)
C5	0.0629 (19)	0.0463 (19)	0.0424 (16)	0.0012 (15)	0.0106 (14)	−0.0048 (14)
C6	0.0529 (16)	0.0249 (14)	0.0412 (14)	0.0020 (12)	0.0144 (12)	0.0007 (12)
C7	0.0408 (14)	0.0305 (15)	0.0380 (14)	0.0011 (11)	0.0041 (11)	−0.0005 (12)
C8	0.077 (2)	0.0326 (17)	0.0394 (15)	0.0029 (15)	0.0132 (14)	0.0054 (13)
C9	0.0376 (13)	0.0302 (15)	0.0328 (13)	−0.0041 (11)	0.0083 (11)	0.0011 (11)
C10	0.0427 (15)	0.0351 (17)	0.0534 (17)	−0.0048 (12)	0.0015 (13)	0.0098 (13)
C11	0.0391 (13)	0.0255 (14)	0.0435 (14)	−0.0005 (11)	0.0077 (11)	−0.0037 (12)
C12	0.0463 (15)	0.0352 (17)	0.0473 (15)	0.0020 (13)	0.0130 (12)	−0.0011 (13)
C13	0.0355 (15)	0.049 (2)	0.076 (2)	0.0001 (13)	0.0098 (14)	−0.0015 (17)
C14	0.053 (2)	0.105 (4)	0.107 (3)	−0.027 (3)	0.028 (2)	−0.015 (3)
C15	0.0406 (17)	0.055 (2)	0.077 (2)	−0.0034 (15)	0.0009 (16)	−0.0108 (19)
C16	0.0549 (19)	0.062 (2)	0.0498 (18)	−0.0013 (17)	0.0010 (14)	−0.0197 (16)
C17	0.0442 (15)	0.0358 (17)	0.0444 (15)	0.0004 (12)	0.0104 (12)	−0.0061 (13)
C18	0.073 (3)	0.143 (5)	0.123 (4)	−0.002 (4)	0.008 (2)	−0.040 (5)
C19	0.099 (3)	0.128 (6)	0.113 (4)	−0.005 (3)	0.036 (3)	−0.031 (4)
C20	0.150 (5)	0.205 (8)	0.113 (4)	0.000 (6)	0.018 (4)	−0.062 (6)
C21	0.111 (5)	0.382 (19)	0.135 (6)	0.027 (8)	−0.006 (4)	−0.050 (9)
Cl1	0.0459 (4)	0.0519 (4)	0.0398 (3)	−0.0060 (3)	0.0103 (2)	0.0042 (3)
N1	0.0385 (10)	0.0302 (12)	0.0327 (10)	−0.0034 (10)	0.0085 (8)	−0.0019 (10)
O1	0.203 (5)	0.154 (5)	0.128 (3)	0.003 (4)	0.077 (3)	−0.049 (3)
O2	0.081 (2)	0.174 (5)	0.119 (3)	0.017 (2)	0.0092 (18)	−0.036 (3)
O3	0.0624 (14)	0.0640 (17)	0.0501 (13)	−0.0141 (12)	0.0226 (11)	−0.0245 (12)
O4	0.126 (2)	0.0545 (17)	0.0411 (12)	0.0029 (15)	0.0262 (15)	0.0052 (12)

Geometric parameters (Å, º)

C1—C2	1.375 (5)	C12—H12	0.9300
C1—C6	1.388 (5)	C13—C15	1.374 (5)
C1—H1	0.9300	C13—C14	1.521 (5)
C2—C3	1.393 (6)	C14—H14A	0.9600
C2—H2	0.9300	C14—H14B	0.9600
C3—C4	1.351 (6)	C14—H14C	0.9600
C3—H3A	0.9300	C15—C16	1.379 (5)
C4—C5	1.378 (5)	C15—H15	0.9300
C4—H4A	0.9300	C16—C17	1.378 (4)
C5—C6	1.383 (4)	C16—H16	0.9300
C5—H5	0.9300	C17—O3	1.370 (4)
C6—C7	1.503 (4)	C18—C19	1.479 (7)
C7—N1	1.499 (4)	C18—H18A	0.9600
C7—C8	1.521 (4)	C18—H18B	0.9600
C7—H7	0.9800	C18—H18C	0.9600
C8—O4	1.416 (4)	C19—O1	1.217 (7)
C8—H8A	0.9700	C19—O2	1.314 (7)
C8—H8B	0.9700	C20—C21	1.391 (8)
C9—C11	1.508 (4)	C20—O2	1.474 (7)
C9—N1	1.510 (3)	C20—H20A	0.9700
C9—C10	1.527 (4)	C20—H20B	0.9700
C9—H9	0.9800	C21—H21A	0.9600
C10—H10A	0.9600	C21—H21B	0.9600
C10—H10B	0.9600	C21—H21C	0.9600
C10—H10C	0.9600	N1—H1A	0.9000
C11—C12	1.382 (4)	N1—H1B	0.9000
C11—C17	1.396 (4)	O3—H3	0.8200
C12—C13	1.390 (4)	O4—H4	0.8200
C2—C1—C6	120.6 (3)	C15—C13—C12	117.5 (3)
C2—C1—H1	119.7	C15—C13—C14	121.6 (3)
C6—C1—H1	119.7	C12—C13—C14	120.9 (3)
C1—C2—C3	119.6 (4)	C13—C14—H14A	109.5
C1—C2—H2	120.2	C13—C14—H14B	109.5
C3—C2—H2	120.2	H14A—C14—H14B	109.5
C4—C3—C2	120.0 (3)	C13—C14—H14C	109.5
C4—C3—H3A	120.0	H14A—C14—H14C	109.5
C2—C3—H3A	120.0	H14B—C14—H14C	109.5
C3—C4—C5	120.8 (4)	C13—C15—C16	121.7 (3)
C3—C4—H4A	119.6	C13—C15—H15	119.2
C5—C4—H4A	119.6	C16—C15—H15	119.2
C4—C5—C6	120.4 (3)	C17—C16—C15	120.1 (3)
C4—C5—H5	119.8	C17—C16—H16	119.9
C6—C5—H5	119.8	C15—C16—H16	119.9
C5—C6—C1	118.7 (3)	O3—C17—C16	123.2 (3)
C5—C6—C7	122.7 (3)	O3—C17—C11	117.0 (2)
C1—C6—C7	118.5 (3)	C16—C17—C11	119.8 (3)
N1—C7—C6	112.4 (2)	C19—C18—H18A	109.5
N1—C7—C8	107.5 (2)	C19—C18—H18B	109.5
C6—C7—C8	112.2 (2)	H18A—C18—H18B	109.5
N1—C7—H7	108.2	C19—C18—H18C	109.5
C6—C7—H7	108.2	H18A—C18—H18C	109.5
C8—C7—H7	108.2	H18B—C18—H18C	109.5
O4—C8—C7	107.9 (3)	O1—C19—O2	118.3 (6)
O4—C8—H8A	110.1	O1—C19—C18	131.4 (7)
C7—C8—H8A	110.1	O2—C19—C18	110.3 (5)
O4—C8—H8B	110.1	C21—C20—O2	107.0 (6)
C7—C8—H8B	110.1	C21—C20—H20A	110.3
H8A—C8—H8B	108.4	O2—C20—H20A	110.3
C11—C9—N1	111.6 (2)	C21—C20—H20B	110.3
C11—C9—C10	112.1 (2)	O2—C20—H20B	110.3
N1—C9—C10	108.8 (2)	H20A—C20—H20B	108.6
C11—C9—H9	108.1	C20—C21—H21A	109.5
N1—C9—H9	108.1	C20—C21—H21B	109.5
C10—C9—H9	108.1	H21A—C21—H21B	109.5
C9—C10—H10A	109.5	C20—C21—H21C	109.5
C9—C10—H10B	109.5	H21A—C21—H21C	109.5
H10A—C10—H10B	109.5	H21B—C21—H21C	109.5
C9—C10—H10C	109.5	C7—N1—C9	115.7 (2)
H10A—C10—H10C	109.5	C7—N1—H1A	108.4
H10B—C10—H10C	109.5	C9—N1—H1A	108.4
C12—C11—C17	118.6 (2)	C7—N1—H1B	108.4
C12—C11—C9	119.6 (2)	C9—N1—H1B	108.4
C17—C11—C9	121.5 (2)	H1A—N1—H1B	107.4
C11—C12—C13	122.3 (3)	C19—O2—C20	113.7 (5)
C11—C12—H12	118.9	C17—O3—H3	109.5
C13—C12—H12	118.9	C8—O4—H4	109.5
C6—C1—C2—C3	1.3 (6)	C9—C11—C12—C13	171.7 (3)
C1—C2—C3—C4	−2.2 (7)	C11—C12—C13—C15	1.2 (5)
C2—C3—C4—C5	1.4 (7)	C11—C12—C13—C14	−178.7 (4)
C3—C4—C5—C6	0.3 (6)	C12—C13—C15—C16	0.5 (6)
C4—C5—C6—C1	−1.2 (5)	C14—C13—C15—C16	−179.7 (4)
C4—C5—C6—C7	−176.9 (3)	C13—C15—C16—C17	−1.3 (6)
C2—C1—C6—C5	0.4 (5)	C15—C16—C17—O3	−179.3 (3)
C2—C1—C6—C7	176.3 (3)	C15—C16—C17—C11	0.4 (5)
C5—C6—C7—N1	−45.3 (4)	C12—C11—C17—O3	−179.1 (3)
C1—C6—C7—N1	139.0 (3)	C9—C11—C17—O3	7.3 (4)
C5—C6—C7—C8	76.1 (4)	C12—C11—C17—C16	1.2 (5)
C1—C6—C7—C8	−99.7 (3)	C9—C11—C17—C16	−172.4 (3)
N1—C7—C8—O4	−53.6 (3)	C6—C7—N1—C9	−62.0 (3)
C6—C7—C8—O4	−177.7 (3)	C8—C7—N1—C9	174.0 (2)
N1—C9—C11—C12	135.5 (3)	C11—C9—N1—C7	−76.6 (3)
C10—C9—C11—C12	−102.1 (3)	C10—C9—N1—C7	159.2 (2)
N1—C9—C11—C17	−50.9 (3)	O1—C19—O2—C20	−3.2 (11)
C10—C9—C11—C17	71.4 (3)	C18—C19—O2—C20	177.0 (7)
C17—C11—C12—C13	−2.0 (4)	C21—C20—O2—C19	176.7 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.90	2.00	2.719 (3)	136
N1—H1A···O3	0.90	2.00	2.719 (3)	136
N1—H1B···Cl1^i	0.90	2.31	3.181 (2)	163
O3—H3···Cl1^ii	0.82	2.21	3.022 (2)	172
O4—H4···Cl1^iii	0.82	2.35	3.149 (3)	164

Symmetry codes: (i) x−1, y, z; (ii) −x+1, y+1/2, −z+2; (iii) −x+1, y−1/2, −z+2.