(R)-1-(2-Hydr­oxy-5-methyl­phen­yl)-N-[(S)-1-(2-meth­oxy-5-methyl­phen­yl)-2-phenyl­ethyl]butan-1-aminium chloride

Zhang, G.-Y.; Li, M.; Wang, W.-H.; Gu, X.-G.

doi:10.1107/S1600536807050714

Buy article online - an online subscription or single-article purchase is required to access this article.

(R)-1-(2-Hydroxy-5-methylphenyl)-N-[(S)-1-(2-methoxy-5-methylphenyl)-2-phenylethyl]butan-1-aminium chloride

G.-Y. Zhang, M. Li, W.-H. Wang and X.-G. Gu

2-{(R)-1-[(S)-1-(2-Methoxy-5-methylphenyl)-2-phenylethylamino]butyl}-4-methylphenol has been synthesized and its absolute configuration determined from the crystal structure of its hydrochloride, the title compound, C₂₇H₃₄NO₂⁺·Cl⁻. The absolute configuration of the stereogenic center that carries the 2-methoxy-5-methylphenyl substituent was found to be R. Intermolecular N—H

Cl and O—H

Cl and intramolecular N—H

O hydrogen bonds stabilize the structure.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050714/sj2377sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050714/sj2377Isup2.hkl Contains datablock I

CCDC reference: 667394

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R factor = 0.039
wR factor = 0.100
Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C19    -   C20     ..       5.23 su

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           25.50
           From the CIF: _reflns_number_total               4534
           Count of symmetry unique reflns         2577
           Completeness (_total/calc)            175.94%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1957
           Fraction of Friedel pairs measured     0.759
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17    = .          R

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The search for new chiral ligands to be used in asymmetric catalysis is of great interest in the field of synthetic chemistry. (Cimarelli et al., 2002; Tseng & Yang, 2004). Among them, enantiopure aminoalkyphenols have attracted wide attention as they can be used in asymmetric catalytic reactions (Puigjaner et al., 1999; Guangyou et al., 2003; Li et al., 2004; Watts et al. 2005), an active area of research in organic chemistry (Joshi & Malhotra, 2003). However, most aminoalkylphenols are derived from readily available natural products (Soai & Niwa, 1992). The synthesis of new aminoalkylphenols is therefore of interest because of their potential as asymmetric catalysts.

In this paper, we report the absolute structure of the title compound (I) a hydrochloride derivative of the aminoalkylphenol 2-((R)-1-((S)-1–2-methoxy-5-methylphenyl-2-phenylethylamino)butyl)-4- methylphenol. As well as the known S configuration of C8, the structure reveals an R configuration for the strereogenic centre at C17. The asymmetric unit of the title compound (Fig. 1) consists of a C₂₇H₃₄NO₂⁺ cation and a Cl^- anion. The dihedral angles between the benzene rings A (C1—C6), B (C9—C15) and C (C21—C27) are 54.51 ° for A/B, 56.51 ° for A/C and 21.17 ° for B/C respectively.

The conformation of the molecule is influenced by two intramolecular N—H···O hydrogen bonds. In the crystal structure, the Cl^- anion forms O—H···Cl and N—H···Cl hydrogen bonds to give a continuous two-dimensional framework structure Table 1, Fig. 2.

Related literature top

For general background, see: Cimarelli et al. (2002); Guangyou et al. (2003); Joshi & Malhotra (2003); Li et al. (2004); Puigjaner et al. (1999); Soai & Niwa (1992); Tseng & Yang (2004); Watts et al. (2005). For related structures, see: Yang et al. (2005).

Experimental top

Compound (II) was prepared according to the procedure of Yang et al. (2005). Compound (II) was reacted at room temperature with concentrated HCl to yield a white precipitate. The solvent was removed and the solid residue recrystallized from an ethanol/hexane (4:1, v/v) mixture to yield compound (I) (m.p. 492–494 K).

Structure description top

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997b); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms represented as spheres of arbitrary radii.
	Fig. 2. Crystal packing of (I); dashed lines indicate hydrogen bonds.

(R)-1-(2-Hydroxy-5-methylphenyl)-N-[(S)-1-(2-methoxy-5-methylphenyl)-2- phenylethyl]butan-1-aminium chloride top

Crystal data top

C₂₇H₃₄NO₂⁺·Cl⁻	F(000) = 944
M_r = 440.00	D_x = 1.194 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4734 reflections
a = 9.8553 (14) Å	θ = 2.3–26.9°
b = 13.1962 (19) Å	µ = 0.18 mm⁻¹
c = 18.825 (3) Å	T = 298 K
V = 2448.2 (6) Å³	Block, colourless
Z = 4	0.48 × 0.40 × 0.32 mm

Data collection top

Bruker SMART CCD area-detecter diffractometer	4534 independent reflections
Radiation source: fine-focus sealed tube	3992 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 25.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997a)	h = −11→11
T_min = 0.919, T_max = 0.945	k = −15→15
12855 measured reflections	l = −22→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0549P)² + 0.1969P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
4534 reflections	Δρ_max = 0.16 e Å⁻³
285 parameters	Δρ_min = −0.15 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1957 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.05 (6)

Crystal data top

C₂₇H₃₄NO₂⁺·Cl⁻	V = 2448.2 (6) Å³
M_r = 440.00	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.8553 (14) Å	µ = 0.18 mm⁻¹
b = 13.1962 (19) Å	T = 298 K
c = 18.825 (3) Å	0.48 × 0.40 × 0.32 mm

Data collection top

Bruker SMART CCD area-detecter diffractometer	4534 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997a)	3992 reflections with I > 2σ(I)
T_min = 0.919, T_max = 0.945	R_int = 0.026
12855 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.100	Δρ_max = 0.16 e Å⁻³
S = 1.03	Δρ_min = −0.15 e Å⁻³
4534 reflections	Absolute structure: Flack (1983), 1957 Friedel pairs
285 parameters	Absolute structure parameter: −0.05 (6)
0 restraints

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
C1	0.5112 (3)	0.44927 (19)	0.38399 (13)	0.0624 (6)
H1	0.5257	0.5105	0.3608	0.075*
C2	0.4101 (3)	0.3849 (2)	0.36021 (17)	0.0802 (9)
H2	0.3591	0.4024	0.3205	0.096*
C3	0.3847 (3)	0.2961 (2)	0.39456 (19)	0.0798 (9)
H3	0.3159	0.2534	0.3790	0.096*
C4	0.4607 (3)	0.2709 (2)	0.45149 (17)	0.0766 (8)
H4	0.4437	0.2103	0.4751	0.092*
C5	0.5633 (3)	0.33371 (18)	0.47519 (14)	0.0608 (6)
H5	0.6147	0.3148	0.5144	0.073*
C6	0.5905 (2)	0.42420 (15)	0.44130 (11)	0.0465 (5)
C7	0.6996 (2)	0.49521 (16)	0.46668 (12)	0.0500 (5)
H7A	0.7391	0.5302	0.4264	0.060*
H7B	0.7709	0.4568	0.4899	0.060*
C8	0.6407 (2)	0.57302 (14)	0.51898 (11)	0.0408 (4)
H8	0.5527	0.5943	0.4999	0.049*
C9	0.6151 (2)	0.53212 (14)	0.59232 (10)	0.0388 (4)
C10	0.4840 (2)	0.52856 (15)	0.61839 (12)	0.0443 (5)
H10	0.4132	0.5502	0.5895	0.053*
C11	0.4545 (2)	0.49376 (16)	0.68641 (13)	0.0530 (5)
C12	0.5602 (2)	0.45930 (17)	0.72691 (13)	0.0573 (6)
H12	0.5424	0.4340	0.7721	0.069*
C13	0.6923 (2)	0.46093 (17)	0.70283 (12)	0.0535 (5)
H13	0.7621	0.4364	0.7313	0.064*
C14	0.72006 (19)	0.49929 (14)	0.63609 (11)	0.0444 (5)
C15	0.3097 (3)	0.4976 (2)	0.71320 (18)	0.0828 (9)
H15A	0.2549	0.4512	0.6864	0.124*
H15B	0.2748	0.5651	0.7077	0.124*
H15C	0.3076	0.4790	0.7625	0.124*
C16	0.9601 (2)	0.4959 (2)	0.65607 (15)	0.0716 (7)
H16A	0.9458	0.5351	0.6984	0.107*
H16B	1.0424	0.5175	0.6334	0.107*
H16C	0.9671	0.4254	0.6683	0.107*
C17	0.6689 (2)	0.75214 (14)	0.56655 (10)	0.0426 (5)
H17	0.5706	0.7415	0.5681	0.051*
C18	0.6927 (3)	0.85349 (15)	0.53024 (12)	0.0524 (5)
H18A	0.7893	0.8674	0.5290	0.063*
H18B	0.6606	0.8497	0.4816	0.063*
C19	0.6206 (3)	0.93971 (18)	0.56818 (15)	0.0762 (8)
H19A	0.5263	0.9212	0.5754	0.091*
H19B	0.6614	0.9491	0.6146	0.091*
C20	0.6263 (4)	1.0368 (2)	0.52876 (17)	0.0946 (10)
H20A	0.7188	1.0517	0.5166	0.142*
H20B	0.5906	1.0901	0.5579	0.142*
H20C	0.5733	1.0313	0.4861	0.142*
C21	0.71962 (19)	0.74655 (13)	0.64187 (10)	0.0413 (4)
C22	0.6296 (2)	0.73690 (15)	0.69791 (11)	0.0465 (5)
H22	0.5371	0.7343	0.6882	0.056*
C23	0.6720 (3)	0.73095 (17)	0.76779 (12)	0.0554 (6)
C24	0.5724 (3)	0.7149 (2)	0.82768 (14)	0.0807 (8)
H24A	0.4818	0.7261	0.8106	0.121*
H24B	0.5917	0.7617	0.8654	0.121*
H24C	0.5803	0.6468	0.8451	0.121*
C25	0.8098 (3)	0.73871 (18)	0.78093 (12)	0.0581 (6)
H25	0.8408	0.7364	0.8276	0.070*
C26	0.9023 (2)	0.74980 (17)	0.72650 (12)	0.0542 (5)
H26	0.9943	0.7556	0.7367	0.065*
C27	0.85830 (19)	0.75234 (15)	0.65706 (10)	0.0437 (5)
N1	0.72890 (17)	0.66615 (12)	0.52202 (8)	0.0419 (4)
H1A	0.7427	0.6888	0.4775	0.050*
H1B	0.8102	0.6490	0.5402	0.050*
O1	0.94600 (13)	0.75705 (13)	0.60056 (7)	0.0544 (4)
H1C	1.0242	0.7609	0.6152	0.082*
O2	0.84902 (14)	0.51013 (12)	0.60891 (8)	0.0544 (4)
Cl1	0.24550 (5)	0.77487 (5)	0.63820 (3)	0.05994 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0754 (16)	0.0561 (13)	0.0558 (14)	0.0171 (13)	−0.0103 (13)	−0.0065 (11)
C2	0.0720 (17)	0.094 (2)	0.0746 (18)	0.0262 (16)	−0.0246 (16)	−0.0237 (18)
C3	0.0617 (16)	0.078 (2)	0.100 (2)	−0.0006 (14)	0.0007 (17)	−0.0346 (18)
C4	0.0858 (18)	0.0517 (14)	0.092 (2)	−0.0097 (14)	0.0121 (17)	−0.0063 (14)
C5	0.0716 (16)	0.0556 (14)	0.0553 (14)	0.0041 (12)	−0.0036 (13)	0.0042 (11)
C6	0.0585 (12)	0.0420 (11)	0.0389 (11)	0.0080 (9)	0.0027 (10)	−0.0065 (9)
C7	0.0540 (12)	0.0513 (12)	0.0449 (11)	0.0008 (10)	0.0058 (10)	−0.0046 (10)
C8	0.0398 (10)	0.0410 (10)	0.0416 (11)	0.0006 (8)	−0.0037 (9)	−0.0001 (8)
C9	0.0425 (10)	0.0347 (9)	0.0392 (11)	0.0006 (8)	−0.0011 (9)	0.0001 (8)
C10	0.0395 (10)	0.0404 (10)	0.0530 (12)	0.0027 (8)	−0.0014 (9)	0.0048 (9)
C11	0.0526 (12)	0.0468 (12)	0.0595 (13)	−0.0027 (10)	0.0099 (11)	0.0079 (11)
C12	0.0689 (15)	0.0530 (12)	0.0501 (13)	−0.0002 (11)	0.0064 (12)	0.0147 (11)
C13	0.0575 (13)	0.0509 (12)	0.0522 (13)	0.0078 (10)	−0.0092 (11)	0.0112 (10)
C14	0.0437 (11)	0.0409 (10)	0.0487 (11)	0.0042 (9)	−0.0026 (9)	−0.0009 (9)
C15	0.0637 (15)	0.0852 (19)	0.099 (2)	0.0069 (15)	0.0311 (16)	0.0299 (17)
C16	0.0501 (12)	0.0897 (18)	0.0751 (17)	0.0157 (13)	−0.0160 (13)	−0.0003 (15)
C17	0.0427 (10)	0.0412 (11)	0.0438 (11)	0.0015 (9)	−0.0007 (9)	−0.0031 (9)
C18	0.0666 (14)	0.0466 (12)	0.0440 (11)	−0.0007 (10)	−0.0109 (11)	0.0021 (9)
C19	0.112 (2)	0.0498 (14)	0.0672 (17)	0.0066 (14)	−0.0046 (17)	−0.0053 (12)
C20	0.141 (3)	0.0593 (15)	0.084 (2)	0.0184 (18)	−0.030 (2)	−0.0071 (15)
C21	0.0461 (10)	0.0360 (9)	0.0417 (10)	0.0006 (8)	−0.0008 (9)	−0.0002 (8)
C22	0.0512 (11)	0.0395 (10)	0.0489 (12)	0.0003 (9)	0.0073 (10)	−0.0019 (9)
C23	0.0738 (15)	0.0475 (12)	0.0449 (12)	0.0054 (11)	0.0129 (11)	0.0023 (10)
C24	0.101 (2)	0.0830 (18)	0.0579 (16)	0.0039 (16)	0.0287 (16)	0.0080 (14)
C25	0.0784 (16)	0.0618 (14)	0.0340 (10)	0.0073 (13)	−0.0051 (11)	0.0002 (10)
C26	0.0569 (12)	0.0582 (13)	0.0474 (12)	0.0036 (11)	−0.0074 (10)	0.0000 (11)
C27	0.0476 (11)	0.0459 (11)	0.0376 (10)	−0.0008 (9)	−0.0009 (9)	−0.0011 (9)
N1	0.0431 (9)	0.0456 (9)	0.0369 (8)	0.0009 (7)	−0.0019 (8)	−0.0018 (7)
O1	0.0426 (7)	0.0778 (11)	0.0429 (8)	−0.0060 (8)	−0.0001 (7)	0.0022 (8)
O2	0.0373 (7)	0.0730 (10)	0.0529 (9)	0.0089 (7)	−0.0032 (7)	0.0043 (8)
Cl1	0.0536 (3)	0.0789 (4)	0.0473 (3)	−0.0029 (3)	−0.0117 (3)	0.0066 (3)

Geometric parameters (Å, º) top

C1—C6	1.372 (3)	C16—H16A	0.9600
C1—C2	1.384 (4)	C16—H16B	0.9600
C1—H1	0.9300	C16—H16C	0.9600
C2—C3	1.361 (4)	C17—C21	1.505 (3)
C2—H2	0.9300	C17—C18	1.520 (3)
C3—C4	1.349 (4)	C17—N1	1.530 (2)
C3—H3	0.9300	C17—H17	0.9800
C4—C5	1.382 (4)	C18—C19	1.520 (3)
C4—H4	0.9300	C18—H18A	0.9700
C5—C6	1.380 (3)	C18—H18B	0.9700
C5—H5	0.9300	C19—C20	1.481 (4)
C6—C7	1.504 (3)	C19—H19A	0.9700
C7—C8	1.536 (3)	C19—H19B	0.9700
C7—H7A	0.9700	C20—H20A	0.9600
C7—H7B	0.9700	C20—H20B	0.9600
C8—C9	1.504 (3)	C20—H20C	0.9600
C8—N1	1.506 (2)	C21—C22	1.385 (3)
C8—H8	0.9800	C21—C27	1.398 (3)
C9—C10	1.383 (3)	C22—C23	1.383 (3)
C9—C14	1.391 (3)	C22—H22	0.9300
C10—C11	1.391 (3)	C23—C25	1.384 (3)
C10—H10	0.9300	C23—C24	1.510 (3)
C11—C12	1.368 (3)	C24—H24A	0.9600
C11—C15	1.515 (3)	C24—H24B	0.9600
C12—C13	1.379 (3)	C24—H24C	0.9600
C12—H12	0.9300	C25—C26	1.379 (3)
C13—C14	1.382 (3)	C25—H25	0.9300
C13—H13	0.9300	C26—C27	1.378 (3)
C14—O2	1.378 (2)	C26—H26	0.9300
C15—H15A	0.9600	C27—O1	1.372 (2)
C15—H15B	0.9600	N1—H1A	0.9000
C15—H15C	0.9600	N1—H1B	0.9000
C16—O2	1.422 (3)	O1—H1C	0.8200

C6—C1—C2	121.1 (3)	H16A—C16—H16C	109.5
C6—C1—H1	119.5	H16B—C16—H16C	109.5
C2—C1—H1	119.5	C21—C17—C18	114.55 (17)
C3—C2—C1	120.5 (3)	C21—C17—N1	110.58 (15)
C3—C2—H2	119.8	C18—C17—N1	110.28 (16)
C1—C2—H2	119.8	C21—C17—H17	107.0
C4—C3—C2	119.2 (3)	C18—C17—H17	107.0
C4—C3—H3	120.4	N1—C17—H17	107.0
C2—C3—H3	120.4	C19—C18—C17	112.03 (19)
C3—C4—C5	121.0 (3)	C19—C18—H18A	109.2
C3—C4—H4	119.5	C17—C18—H18A	109.2
C5—C4—H4	119.5	C19—C18—H18B	109.2
C6—C5—C4	120.8 (3)	C17—C18—H18B	109.2
C6—C5—H5	119.6	H18A—C18—H18B	107.9
C4—C5—H5	119.6	C20—C19—C18	113.2 (2)
C1—C6—C5	117.5 (2)	C20—C19—H19A	108.9
C1—C6—C7	120.4 (2)	C18—C19—H19A	108.9
C5—C6—C7	122.1 (2)	C20—C19—H19B	108.9
C6—C7—C8	110.46 (17)	C18—C19—H19B	108.9
C6—C7—H7A	109.6	H19A—C19—H19B	107.8
C8—C7—H7A	109.6	C19—C20—H20A	109.5
C6—C7—H7B	109.6	C19—C20—H20B	109.5
C8—C7—H7B	109.6	H20A—C20—H20B	109.5
H7A—C7—H7B	108.1	C19—C20—H20C	109.5
C9—C8—N1	110.78 (15)	H20A—C20—H20C	109.5
C9—C8—C7	114.31 (16)	H20B—C20—H20C	109.5
N1—C8—C7	110.58 (16)	C22—C21—C27	118.40 (18)
C9—C8—H8	106.9	C22—C21—C17	120.64 (17)
N1—C8—H8	106.9	C27—C21—C17	120.96 (17)
C7—C8—H8	106.9	C23—C22—C21	122.4 (2)
C10—C9—C14	118.27 (18)	C23—C22—H22	118.8
C10—C9—C8	119.65 (18)	C21—C22—H22	118.8
C14—C9—C8	122.07 (18)	C22—C23—C25	117.6 (2)
C9—C10—C11	122.22 (19)	C22—C23—C24	121.4 (2)
C9—C10—H10	118.9	C25—C23—C24	121.0 (2)
C11—C10—H10	118.9	C23—C24—H24A	109.5
C12—C11—C10	117.6 (2)	C23—C24—H24B	109.5
C12—C11—C15	122.9 (2)	H24A—C24—H24B	109.5
C10—C11—C15	119.5 (2)	C23—C24—H24C	109.5
C11—C12—C13	122.0 (2)	H24A—C24—H24C	109.5
C11—C12—H12	119.0	H24B—C24—H24C	109.5
C13—C12—H12	119.0	C26—C25—C23	121.6 (2)
C12—C13—C14	119.4 (2)	C26—C25—H25	119.2
C12—C13—H13	120.3	C23—C25—H25	119.2
C14—C13—H13	120.3	C27—C26—C25	120.0 (2)
O2—C14—C13	123.95 (19)	C27—C26—H26	120.0
O2—C14—C9	115.68 (18)	C25—C26—H26	120.0
C13—C14—C9	120.36 (19)	O1—C27—C26	122.58 (18)
C11—C15—H15A	109.5	O1—C27—C21	117.36 (17)
C11—C15—H15B	109.5	C26—C27—C21	120.02 (19)
H15A—C15—H15B	109.5	C8—N1—C17	113.77 (14)
C11—C15—H15C	109.5	C8—N1—H1A	108.8
H15A—C15—H15C	109.5	C17—N1—H1A	108.8
H15B—C15—H15C	109.5	C8—N1—H1B	108.8
O2—C16—H16A	109.5	C17—N1—H1B	108.8
O2—C16—H16B	109.5	H1A—N1—H1B	107.7
H16A—C16—H16B	109.5	C27—O1—H1C	109.5
O2—C16—H16C	109.5	C14—O2—C16	117.69 (17)

C6—C1—C2—C3	1.8 (4)	C8—C9—C14—C13	−179.15 (19)
C1—C2—C3—C4	−1.0 (4)	C21—C17—C18—C19	−61.2 (3)
C2—C3—C4—C5	0.0 (4)	N1—C17—C18—C19	173.31 (19)
C3—C4—C5—C6	0.2 (4)	C17—C18—C19—C20	−172.2 (2)
C2—C1—C6—C5	−1.5 (3)	C18—C17—C21—C22	113.4 (2)
C2—C1—C6—C7	−179.8 (2)	N1—C17—C21—C22	−121.26 (19)
C4—C5—C6—C1	0.5 (3)	C18—C17—C21—C27	−65.7 (2)
C4—C5—C6—C7	178.7 (2)	N1—C17—C21—C27	59.6 (2)
C1—C6—C7—C8	86.5 (2)	C27—C21—C22—C23	−1.2 (3)
C5—C6—C7—C8	−91.7 (2)	C17—C21—C22—C23	179.64 (19)
C6—C7—C8—C9	76.7 (2)	C21—C22—C23—C25	2.3 (3)
C6—C7—C8—N1	−157.42 (17)	C21—C22—C23—C24	−176.7 (2)
N1—C8—C9—C10	117.71 (19)	C22—C23—C25—C26	−1.4 (4)
C7—C8—C9—C10	−116.6 (2)	C24—C23—C25—C26	177.7 (2)
N1—C8—C9—C14	−60.9 (2)	C23—C25—C26—C27	−0.7 (4)
C7—C8—C9—C14	64.9 (2)	C25—C26—C27—O1	−176.0 (2)
C14—C9—C10—C11	0.2 (3)	C25—C26—C27—C21	1.8 (3)
C8—C9—C10—C11	−178.45 (19)	C22—C21—C27—O1	177.00 (17)
C9—C10—C11—C12	−2.1 (3)	C17—C21—C27—O1	−3.9 (3)
C9—C10—C11—C15	176.4 (2)	C22—C21—C27—C26	−0.9 (3)
C10—C11—C12—C13	1.7 (4)	C17—C21—C27—C26	178.25 (18)
C15—C11—C12—C13	−176.8 (2)	C9—C8—N1—C17	−58.7 (2)
C11—C12—C13—C14	0.6 (4)	C7—C8—N1—C17	173.50 (16)
C12—C13—C14—O2	175.8 (2)	C21—C17—N1—C8	93.05 (18)
C12—C13—C14—C9	−2.7 (3)	C18—C17—N1—C8	−139.22 (17)
C10—C9—C14—O2	−176.33 (17)	C13—C14—O2—C16	−10.1 (3)
C8—C9—C14—O2	2.3 (3)	C9—C14—O2—C16	168.4 (2)
C10—C9—C14—C13	2.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···Cl1ⁱ	0.82	2.23	3.0446 (15)	171
N1—H1A···Cl1ⁱⁱ	0.90	2.23	3.1193 (18)	169
N1—H1B···O2	0.90	2.28	2.884 (2)	125
N1—H1B···O1	0.90	2.26	2.864 (2)	124

Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₇H₃₄NO₂⁺·Cl⁻
M_r	440.00
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	9.8553 (14), 13.1962 (19), 18.825 (3)
V (Å³)	2448.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.48 × 0.40 × 0.32

Data collection
Diffractometer	Bruker SMART CCD area-detecter
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997a)
T_min, T_max	0.919, 0.945
No. of measured, independent and observed [I > 2σ(I)] reflections	12855, 4534, 3992
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.100, 1.03
No. of reflections	4534
No. of parameters	285
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.15
Absolute structure	Flack (1983), 1957 Friedel pairs
Absolute structure parameter	−0.05 (6)

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997b), SHELXL97 (Sheldrick, 1997b), PLATON (Spek, 2003), SHELXTL (Bruker, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···Cl1ⁱ	0.82	2.23	3.0446 (15)	171.4
N1—H1A···Cl1ⁱⁱ	0.90	2.23	3.1193 (18)	169.3
N1—H1B···O2	0.90	2.28	2.884 (2)	124.7
N1—H1B···O1	0.90	2.26	2.864 (2)	124.0

Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+3/2, −z+1.

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page