(R)-N-[(R)-1-(2-Hydroxy-5-methyl­phenyl)-2-phenyl­ethyl]-2-methyl-1-phenyl­propyl­ammonium chloride

In the title compound, C₂₅H₃₀NO⁺·Cl⁻, the mol­ecules are linked by a combination of inter­molecular N—H...Cl and O—H...Cl hydrogen bonds and intra­molecular N—H...O hydrogen bonds. The absolute configuration of the new stereogenic centre (the C atom adjacent to the N atom on the phenol side) is determined to have an R configuration.

S1. Comment

The synthesis of enantiopure amine alcohols with a variety of functionalities is an important subject of research because this class of compounds are widespread in natural products, show pharmacological activity and have recently found application in asymmetric synthesis as chiral bases, auxiliaries and ligands (Cimarelli et al., 2002). Chiral aminophenols, which are similar to amino alcohols, are important building blocks in organic synthesis, and have attracted increasing attention in recent years owing to their effect in asymmetric synthesis and asymmetric induction (Cimarelli & Palmieri, 2000; Cimarelli et al., 2001; Palmieri 2000; Xu et al., 2002, and references therein).

As part of our continuing studies of chiral aminophenols, we have established the molecular structure of 4-methyl-2-[(1R)-1-{[(1R)-2-methyl-1-phenylpropyl]amino}phenylethyl]phenol, (II), which was initially prepared to test its asymmetric catalytic activity. Aminoalkylphenol (II) was prepared by conventional condensation of (R)-2-methyl-1-phenylpropan-1-amine with 1-(2-hydroxy-5-methylphenyl)-2-phenylethanone, followed by reduction using sodium borohydride in a tetrahydrofuran–ethanol (1:1 v/v) mixture. The isolated yield and the diastereoisomeric excess, d.e. (determined by chiral high-performance liquid chromatography), are 82.7 and 99.5%, respectively. Compound (R,R)-(II) was obtained as the main product.

In addition to the synthesis of the novel chiral aminoalkylphenol, (II), its hydrochloride, (I), was also synthesized. The occurrence of a Cl atom in compound (I) helps in establishing the absolute configuration of the compound and thus in deducing the absolute configuration of (II). Therefore, an X-ray study of the title compound, (I), was carried out and we present the results here.

Selected bond lengths and angles of (I), including those of the new stereogenic carbon centre (C8), are reported in Table 1. As shown in Fig. 1, the absolute configuration of (I) is (R,R), so it can be deduced that the absolute configuration of (II) is also (R,R).

An extensive network of hydrogen bonds, listed in Table 2, appears to be a key factor in the stabilization of this structure. The molecules of compound (I) (Fig. 1) are linked by a combination of intermolecular N—H···Cl and O—H···Cl hydrogen bonds, and intramolecular N—H···O hydrogen bonds (Fig. 1). An interesting feature of the structure is that the intermolecular N—H···Cl and O—H···Cl hydrogen-bonding interactions result in the formation of helical chains running parallel to the b axis (Fig. 2). Atom N1 acts as a hydrogen-bond donor to phenol atom O1, with N···O = 2.711 (3) Å, which indicates a comparatively strong intramolecular hydrogen bond (Table 2). No aromatic π–π stacking interactions are present in the structure of (I).

The terminal benzene rings are neither parallel nor normal to each other [interplanar angles: 49.17 (12)° for A/B, 62.74 (12)° for B/C and 15.39 (15)° for A/C; rings are as defined in Fig. 1].

S2. Experimental

The title compound was prepared according to the procedure of Yang et al. (2005). (R)-2-Methyl-1-phenylpropan-1-amine (0.9 mmol) and 1-(2-hydroxy-5-methylphenyl)-2-phenylethanone (0.9 mmol) were dissolved in methanol (10 ml) and reacted at room temperature for 48 h. After removal of the solvent, NaBH₄ (4.5 mmol) was added to the solution in tetrahydrofuran–ethanol (20 ml; 1:1 v/v) and stirred at 273 K until the solution became colourless. The solvent was then removed under reduced pressure. Water (Volume?) was added to the residue and 1 N HCl was added dropwise until hydrogen production ceased, and the mixture was then neutralized with aqueous Na₂CO₃. The mixture was then extracted with CHCl₃ and the organic layer was dried over anhydrous sodium sulfate. The solvent was then removed under reduced pressure. Further purification was carried out by thin-layer silica-gel chromatography (chloroform) to give chiral (II) [colourless solid; yield 86.3%; [α]²²_D = 84.1 (c_0.5, CHCl₃)]. Compound (II) (Quantity?) and concentrated HCl (Volume?) were reacted in methanol (Volume?) at room temperature. The solvent was removed and the solid residue was recrystallized from a mixed solvent of ethyl acetate and ethanol (95:1 v/v) to yield compound (I) (m.p. 475–476 K).

S3. Refinement

All H atoms were included in calculated positions and treated as riding on their parent atoms, with N—H = 0.90, O—H = 0.82, C—H(aromatic) = 0.93, C—H(methyl) = 0.96, C—H(methylene) = 0.97 and C—H(methine) = 0.98 Å, and with U_iso(H) = 1.2U_eq(C,N,O), or 1.5U_eq(CH₃).

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); 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.

Figures

	Fig. 1. The asymmetric unit of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as spheres of arbitrary radii. Hydrogen bonds are indicated by double dashed lines. [Symmetry code: (i) ? Please provide symmetry code.]
	Fig. 2. A packing diagram of (I), viewed down the a axis, showing the formation of helical chains through N—H···Cl and O—H···Cl hydrogen bonds (double dashed lines) along b. H atoms not involved in hydrogen bonding have been omitted. [Symmetry codes: (i) ?; (ii) ?; (iii) ? Please provide symmetry codes.]

(R)—N-[(R)-1-(2-Hydroxy-5-methylphenyl)-2-phenylethyl]-2-methyl-1- phenylpropylammonium chloride

Crystal data

C25H30NO^+·Cl^−	F(000) = 848
Mr = 395.95	Dx = 1.148 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P2ac2ab	Cell parameters from 1603 reflections
a = 9.964 (2) Å	θ = 2.3–18.8°
b = 11.565 (2) Å	µ = 0.18 mm^−1
c = 19.882 (4) Å	T = 298 K
V = 2291.1 (8) Å^3	Block, colourless
Z = 4	0.21 × 0.15 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4040 independent reflections
Radiation source: fine-focus sealed tube	2725 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
ϕ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −6→11
Tmin = 0.962, Tmax = 0.981	k = −12→13
11656 measured reflections	l = −23→23

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)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.0373P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max = 0.001
4040 reflections	Δρmax = 0.31 e Å^−3
257 parameters	Δρmin = −0.13 e Å^−3
0 restraints	Absolute structure: Flack (1983), with 1736 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.07 (8)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1463 (3)	0.5176 (2)	0.88723 (14)	0.0467 (8)
C2	0.1408 (4)	0.6082 (3)	0.93194 (14)	0.0526 (8)
H2	0.0649	0.6549	0.9339	0.063*
C3	0.2478 (4)	0.6295 (3)	0.97370 (16)	0.0564 (9)
H3	0.2435	0.6914	1.0034	0.068*
C4	0.3614 (3)	0.5614 (3)	0.97276 (14)	0.0492 (8)
C5	0.4820 (4)	0.5902 (3)	1.01569 (17)	0.0786 (11)
H5A	0.5198	0.5202	1.0334	0.118*
H5B	0.4549	0.6395	1.0521	0.118*
H5C	0.5479	0.6293	0.9888	0.118*
C6	0.3634 (3)	0.4690 (2)	0.92814 (13)	0.0446 (8)
H6	0.4387	0.4216	0.9267	0.053*
C7	0.2567 (3)	0.4451 (2)	0.88567 (13)	0.0392 (7)
C8	0.2611 (3)	0.3412 (2)	0.83939 (11)	0.0410 (7)
H8	0.3523	0.3096	0.8398	0.049*
C9	0.1629 (3)	0.2444 (2)	0.85856 (14)	0.0515 (8)
H9A	0.0755	0.2778	0.8678	0.062*
H9B	0.1533	0.1917	0.8209	0.062*
C10	0.2099 (3)	0.1779 (3)	0.91947 (13)	0.0470 (8)
C11	0.1790 (4)	0.2133 (3)	0.98405 (15)	0.0690 (11)
H11	0.1273	0.2793	0.9906	0.083*
C12	0.2245 (5)	0.1511 (3)	1.03900 (17)	0.0907 (15)
H12	0.2037	0.1758	1.0823	0.109*
C13	0.2990 (4)	0.0547 (4)	1.0301 (2)	0.0942 (14)
H13	0.3305	0.0142	1.0673	0.113*
C14	0.3283 (4)	0.0166 (4)	0.9670 (2)	0.0943 (13)
H14	0.3776	−0.0509	0.9610	0.113*
C15	0.2840 (4)	0.0791 (3)	0.91200 (17)	0.0727 (11)
H15	0.3051	0.0535	0.8690	0.087*
C16	0.3237 (3)	0.4615 (2)	0.73565 (13)	0.0438 (8)
H16	0.3304	0.5298	0.7646	0.053*
C17	0.2646 (4)	0.5003 (3)	0.66817 (15)	0.0598 (9)
H17	0.2578	0.4325	0.6388	0.072*
C18	0.1256 (4)	0.5526 (3)	0.67546 (16)	0.0877 (12)
H18A	0.0630	0.4935	0.6883	0.132*
H18B	0.0984	0.5858	0.6333	0.132*
H18C	0.1274	0.6117	0.7094	0.132*
C19	0.3581 (5)	0.5866 (3)	0.63542 (18)	0.1053 (15)
H19A	0.3659	0.6538	0.6635	0.158*
H19B	0.3228	0.6087	0.5924	0.158*
H19C	0.4450	0.5522	0.6296	0.158*
C20	0.4622 (3)	0.4092 (2)	0.73013 (14)	0.0442 (8)
C21	0.5691 (4)	0.4562 (3)	0.76413 (15)	0.0575 (9)
H21	0.5541	0.5179	0.7932	0.069*
C22	0.6982 (4)	0.4145 (4)	0.75654 (19)	0.0754 (11)
H22	0.7693	0.4485	0.7795	0.090*
C23	0.7197 (4)	0.3219 (3)	0.7144 (2)	0.0759 (11)
H23	0.8059	0.2926	0.7090	0.091*
C24	0.6153 (4)	0.2728 (3)	0.68051 (18)	0.0671 (10)
H24	0.6306	0.2103	0.6520	0.080*
C25	0.4874 (4)	0.3154 (3)	0.68839 (14)	0.0532 (8)
H25	0.4167	0.2809	0.6654	0.064*
Cl1	0.15209 (11)	0.18788 (7)	0.66694 (4)	0.0772 (3)
N1	0.2278 (2)	0.37861 (18)	0.76843 (10)	0.0420 (6)
H1A	0.2226	0.3149	0.7426	0.050*
H1B	0.1459	0.4115	0.7688	0.050*
O1	0.0433 (2)	0.49385 (17)	0.84297 (11)	0.0578 (6)
H1	−0.0019	0.5522	0.8373	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.044 (2)	0.0520 (19)	0.0442 (16)	−0.0006 (18)	−0.0025 (18)	−0.0014 (14)
C2	0.050 (2)	0.0526 (18)	0.0552 (18)	0.0068 (18)	0.0027 (19)	−0.0128 (16)
C3	0.069 (3)	0.0454 (18)	0.0542 (18)	−0.006 (2)	0.009 (2)	−0.0159 (16)
C4	0.052 (2)	0.0521 (19)	0.0436 (17)	−0.0124 (19)	0.0010 (18)	−0.0027 (15)
C5	0.078 (3)	0.083 (3)	0.075 (2)	−0.009 (2)	−0.021 (2)	−0.020 (2)
C6	0.049 (2)	0.0430 (17)	0.0421 (16)	−0.0010 (16)	−0.0018 (17)	0.0022 (14)
C7	0.042 (2)	0.0417 (16)	0.0341 (14)	−0.0016 (16)	−0.0001 (16)	0.0013 (13)
C8	0.0463 (19)	0.0394 (16)	0.0372 (15)	−0.0019 (14)	−0.0027 (16)	0.0021 (13)
C9	0.060 (2)	0.0471 (16)	0.0478 (16)	−0.0111 (18)	−0.0019 (18)	−0.0024 (14)
C10	0.057 (2)	0.0411 (16)	0.0426 (17)	−0.0123 (18)	0.0009 (16)	0.0040 (15)
C11	0.108 (3)	0.044 (2)	0.054 (2)	−0.006 (2)	0.004 (2)	−0.0059 (16)
C12	0.154 (5)	0.073 (3)	0.045 (2)	−0.021 (3)	−0.011 (3)	0.006 (2)
C13	0.101 (4)	0.099 (3)	0.083 (3)	−0.005 (3)	−0.033 (3)	0.036 (3)
C14	0.091 (3)	0.092 (3)	0.099 (3)	0.025 (3)	0.010 (3)	0.023 (3)
C15	0.083 (3)	0.074 (2)	0.061 (2)	0.017 (2)	0.019 (2)	0.0049 (19)
C16	0.058 (2)	0.0325 (15)	0.0413 (16)	−0.0026 (16)	0.0031 (17)	−0.0012 (13)
C17	0.077 (3)	0.0557 (18)	0.0472 (17)	0.0193 (19)	0.004 (2)	0.0057 (16)
C18	0.093 (3)	0.099 (3)	0.072 (2)	0.038 (3)	−0.010 (3)	0.017 (2)
C19	0.121 (4)	0.104 (3)	0.092 (3)	0.017 (3)	0.026 (3)	0.057 (3)
C20	0.054 (2)	0.0364 (17)	0.0420 (16)	−0.0031 (16)	0.0063 (18)	0.0091 (14)
C21	0.065 (3)	0.056 (2)	0.0517 (19)	−0.016 (2)	0.006 (2)	−0.0002 (17)
C22	0.055 (3)	0.087 (3)	0.084 (3)	−0.012 (2)	−0.005 (2)	0.011 (2)
C23	0.055 (3)	0.076 (3)	0.097 (3)	0.008 (3)	0.015 (3)	0.016 (3)
C24	0.067 (3)	0.059 (2)	0.075 (2)	0.009 (2)	0.012 (2)	−0.0034 (18)
C25	0.057 (2)	0.0452 (17)	0.0572 (19)	0.0023 (19)	0.0032 (18)	−0.0053 (17)
Cl1	0.0950 (8)	0.0655 (5)	0.0712 (5)	−0.0223 (6)	−0.0194 (6)	−0.0136 (5)
N1	0.0440 (16)	0.0408 (13)	0.0412 (12)	0.0002 (13)	−0.0044 (13)	−0.0021 (11)
O1	0.0460 (14)	0.0664 (14)	0.0609 (12)	0.0099 (11)	−0.0092 (13)	−0.0108 (13)

Geometric parameters (Å, º)

C1—C2	1.376 (4)	C14—H14	0.9300
C1—O1	1.379 (3)	C15—H15	0.9300
C1—C7	1.383 (4)	C16—N1	1.502 (3)
C2—C3	1.374 (4)	C16—C20	1.510 (4)
C2—H2	0.9300	C16—C17	1.533 (4)
C3—C4	1.379 (4)	C16—H16	0.9800
C3—H3	0.9300	C17—C19	1.514 (4)
C4—C6	1.389 (4)	C17—C18	1.519 (4)
C4—C5	1.511 (4)	C17—H17	0.9800
C5—H5A	0.9600	C18—H18A	0.9600
C5—H5B	0.9600	C18—H18B	0.9600
C5—H5C	0.9600	C18—H18C	0.9600
C6—C7	1.385 (4)	C19—H19A	0.9600
C6—H6	0.9300	C19—H19B	0.9600
C7—C8	1.515 (3)	C19—H19C	0.9600
C8—N1	1.513 (3)	C20—C21	1.373 (4)
C8—C9	1.535 (4)	C20—C25	1.389 (4)
C8—H8	0.9800	C21—C22	1.382 (5)
C9—C10	1.509 (4)	C21—H21	0.9300
C9—H9A	0.9700	C22—C23	1.377 (5)
C9—H9B	0.9700	C22—H22	0.9300
C10—C15	1.368 (4)	C23—C24	1.363 (5)
C10—C11	1.382 (4)	C23—H23	0.9300
C11—C12	1.385 (5)	C24—C25	1.375 (4)
C11—H11	0.9300	C24—H24	0.9300
C12—C13	1.350 (5)	C25—H25	0.9300
C12—H12	0.9300	N1—H1A	0.9000
C13—C14	1.361 (5)	N1—H1B	0.9000
C13—H13	0.9300	O1—H1	0.8200
C14—C15	1.384 (5)
C2—C1—O1	122.3 (3)	C10—C15—H15	119.2
C2—C1—C7	120.5 (3)	C14—C15—H15	119.2
O1—C1—C7	117.2 (2)	N1—C16—C20	111.0 (2)
C3—C2—C1	119.7 (3)	N1—C16—C17	108.8 (2)
C3—C2—H2	120.1	C20—C16—C17	113.9 (2)
C1—C2—H2	120.1	N1—C16—H16	107.7
C2—C3—C4	121.8 (3)	C20—C16—H16	107.7
C2—C3—H3	119.1	C17—C16—H16	107.7
C4—C3—H3	119.1	C19—C17—C18	109.8 (3)
C3—C4—C6	117.3 (3)	C19—C17—C16	109.5 (3)
C3—C4—C5	121.3 (3)	C18—C17—C16	112.6 (3)
C6—C4—C5	121.3 (3)	C19—C17—H17	108.3
C4—C5—H5A	109.5	C18—C17—H17	108.3
C4—C5—H5B	109.5	C16—C17—H17	108.3
H5A—C5—H5B	109.5	C17—C18—H18A	109.5
C4—C5—H5C	109.5	C17—C18—H18B	109.5
H5A—C5—H5C	109.5	H18A—C18—H18B	109.5
H5B—C5—H5C	109.5	C17—C18—H18C	109.5
C7—C6—C4	122.2 (3)	H18A—C18—H18C	109.5
C7—C6—H6	118.9	H18B—C18—H18C	109.5
C4—C6—H6	118.9	C17—C19—H19A	109.5
C1—C7—C6	118.4 (3)	C17—C19—H19B	109.5
C1—C7—C8	121.1 (3)	H19A—C19—H19B	109.5
C6—C7—C8	120.4 (3)	C17—C19—H19C	109.5
N1—C8—C7	109.5 (2)	H19A—C19—H19C	109.5
N1—C8—C9	107.5 (2)	H19B—C19—H19C	109.5
C7—C8—C9	114.2 (2)	C21—C20—C25	117.6 (3)
N1—C8—H8	108.5	C21—C20—C16	121.0 (3)
C7—C8—H8	108.5	C25—C20—C16	121.4 (3)
C9—C8—H8	108.5	C20—C21—C22	122.0 (3)
C10—C9—C8	111.9 (2)	C20—C21—H21	119.0
C10—C9—H9A	109.2	C22—C21—H21	119.0
C8—C9—H9A	109.2	C23—C22—C21	118.8 (4)
C10—C9—H9B	109.2	C23—C22—H22	120.6
C8—C9—H9B	109.2	C21—C22—H22	120.6
H9A—C9—H9B	107.9	C24—C23—C22	120.4 (4)
C15—C10—C11	117.9 (3)	C24—C23—H23	119.8
C15—C10—C9	120.4 (3)	C22—C23—H23	119.8
C11—C10—C9	121.7 (3)	C23—C24—C25	120.1 (3)
C10—C11—C12	120.4 (3)	C23—C24—H24	120.0
C10—C11—H11	119.8	C25—C24—H24	120.0
C12—C11—H11	119.8	C24—C25—C20	121.1 (3)
C13—C12—C11	120.4 (4)	C24—C25—H25	119.5
C13—C12—H12	119.8	C20—C25—H25	119.5
C11—C12—H12	119.8	C16—N1—C8	116.6 (2)
C12—C13—C14	120.4 (4)	C16—N1—H1A	108.1
C12—C13—H13	119.8	C8—N1—H1A	108.1
C14—C13—H13	119.8	C16—N1—H1B	108.1
C13—C14—C15	119.4 (4)	C8—N1—H1B	108.1
C13—C14—H14	120.3	H1A—N1—H1B	107.3
C15—C14—H14	120.3	C1—O1—H1	109.5
C10—C15—C14	121.5 (3)	C1—O1—H1	109.5
O1—C1—C2—C3	−178.4 (3)	C12—C13—C14—C15	1.7 (7)
C7—C1—C2—C3	2.4 (4)	C11—C10—C15—C14	−0.6 (6)
C1—C2—C3—C4	−0.7 (5)	C9—C10—C15—C14	−180.0 (3)
C2—C3—C4—C6	−0.6 (4)	C13—C14—C15—C10	−0.8 (6)
C2—C3—C4—C5	176.0 (3)	N1—C16—C17—C19	178.3 (2)
C3—C4—C6—C7	0.3 (4)	C20—C16—C17—C19	−57.4 (3)
C5—C4—C6—C7	−176.3 (3)	N1—C16—C17—C18	55.8 (3)
C2—C1—C7—C6	−2.6 (4)	C20—C16—C17—C18	−179.9 (3)
O1—C1—C7—C6	178.1 (2)	N1—C16—C20—C21	−115.8 (3)
C2—C1—C7—C8	176.6 (2)	C17—C16—C20—C21	121.1 (3)
O1—C1—C7—C8	−2.7 (4)	N1—C16—C20—C25	67.1 (3)
C4—C6—C7—C1	1.3 (4)	C17—C16—C20—C25	−56.1 (3)
C4—C6—C7—C8	−178.0 (2)	C25—C20—C21—C22	1.5 (4)
C1—C7—C8—N1	51.8 (3)	C16—C20—C21—C22	−175.8 (3)
C6—C7—C8—N1	−128.9 (3)	C20—C21—C22—C23	−1.1 (5)
C1—C7—C8—C9	−68.7 (3)	C21—C22—C23—C24	0.4 (5)
C6—C7—C8—C9	110.5 (3)	C22—C23—C24—C25	−0.2 (5)
N1—C8—C9—C10	163.9 (2)	C23—C24—C25—C20	0.6 (5)
C7—C8—C9—C10	−74.5 (3)	C21—C20—C25—C24	−1.2 (4)
C8—C9—C10—C15	−93.5 (3)	C16—C20—C25—C24	176.0 (3)
C8—C9—C10—C11	87.2 (4)	C20—C16—N1—C8	60.8 (3)
C15—C10—C11—C12	1.2 (5)	C17—C16—N1—C8	−173.2 (2)
C9—C10—C11—C12	−179.4 (3)	C7—C8—N1—C16	63.7 (3)
C10—C11—C12—C13	−0.4 (6)	C9—C8—N1—C16	−171.8 (2)
C11—C12—C13—C14	−1.1 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl1^i	0.82	2.17	2.978 (2)	169
N1—H1B···O1	0.90	2.03	2.711 (3)	131
N1—H1A···Cl1	0.90	2.22	3.083 (2)	162

Symmetry code: (i) −x, y+1/2, −z+3/2.