(4R)-4-(Biphenyl-4-yl)-7-chloro-1,2,3,4-tetra­hydro­quinoline

Theissmann, T.; Bolte, M.

doi:10.1107/S160053681103830X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2747

https://doi.org/10.1107/S160053681103830X

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(4R)-4-(Biphenyl-4-yl)-7-chloro-1,2,3,4-tetrahydroquinoline

Thomas Theissmann ^a and Michael Bolte ^b ^*

^aInstitute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, and ^bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Str. 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: bolte@chemie.uni-frankfurt.de

(Received 9 September 2011; accepted 19 September 2011; online 30 September 2011)

The title compound, C₂₁H₁₈ClN, was synthesized by an enantioselective Brønsted acid-catalysed transfer hydrogenation reaction. The six-membered heterocycle adopts a half-chair conformation. It has the biphenyl residue in an axial position. The two rings of the biphenyl residue are almost coplanar [dihedral angle = 2.65 (9)°]. The crystal packing is stabilized by N—H⋯Cl hydrogen bonds, which connect the molecules into chains running along the a axis.

Related literature

For organocatalysed processes, see: Rueping, Sugiono & Schoepke (2010 ); Rueping, Dufour & Schoepke (2011 ). For Brønsted acid-catalysed transfer hydrogenations, see: Rueping et al. (2008 ); Rueping, Stoeckel et al. (2010 ). For the synthesis of the title compound, see: Rueping, Theissmann et al. (2011 ).

Experimental

Crystal data

C₂₁H₁₈ClN
M_r = 319.81
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.5354 (4) Å
b = 8.0039 (4) Å
c = 35.8207 (17) Å
V = 1587.03 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 173 K
0.35 × 0.21 × 0.11 mm

Data collection

STOE IPDS II two-circle-diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2009 ; Blessing, 1995 ) T_min = 0.921, T_max = 0.984
18042 measured reflections
3071 independent reflections
2867 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.079
S = 1.05
3071 reflections
213 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack (1983 ), 1240 Friedel pairs
Flack parameter: 0.01 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1ⁱ	0.90 (3)	2.66 (3)	3.5466 (17)	171 (2)
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: X-AREA (Stoe & Cie, 2001 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681103830X/lr2028sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681103830X/lr2028Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681103830X/lr2028Isup3.cml

checkCIF report

Comment top

Tetrahydroquinolines are widely distributed in nature. Due to their importance as synthetic intermediates in the preparation of pharmaceuticals, agrochemicals, and in material science, considerable effort has been made to prepare these important molecules. Recently organocatalyzed processes have found widespread applications (Rueping, Sugiono & Schoepke, 2010; Rueping, Dufour & Schoepke, 2011). In particular Brønsted acid catalyzed transfer hydrogenations have been reported to provide a series of N-heterocyclic compounds with highest enantioselectivities (Rueping et al., 2008; Rueping, Stoeckel et al., 2010). The title compound was synthesized for the first time following this methodology (Rueping, Theissmann et al., 2011) and colourless plates suitable for crystal structure determination were obtained.

The six-membered heterocycle in the title compound adopts a half chair conformation. It has the biphenyl residue in an axial position. The two rings of the biphenyl residue are almost coplanar [dihedral angle 2.65 (9)°]. The crystal packing is stabilized by N—H···Cl hydrogen bonds connecting the molecules to chains running along the a axis.

Related literature top

For organocatalysed processes, see: Rueping, Sugiono & Schoepke (2010); Rueping, Dufour & Schoepke (2011). For Brønsted acid-catalysed transfer hydrogenations, see: Rueping et al. (2008); Rueping, Stoeckel et al. (2010). For the synthesis of the title compound, see: Rueping, Theissmann et al. (2011).

Experimental top

The title compound has been synthesized as described by Rueping, Theissmann et al. (2011).

Structure description top

For organocatalysed processes, see: Rueping, Sugiono & Schoepke (2010); Rueping, Dufour & Schoepke (2011). For Brønsted acid-catalysed transfer hydrogenations, see: Rueping et al. (2008); Rueping, Stoeckel et al. (2010). For the synthesis of the title compound, see: Rueping, Theissmann et al. (2011).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level.
	Fig. 2. Packing diagram of the title compound. Hydrogen atoms bonded to C have been omitted for clarity. Hydrogen bonds are drawn as dashed lines.

(4R)-4-(biphenyl-4-yl)-7-chloro-1,2,3,4-tetrahydroquinoline top

Crystal data top

C₂₁H₁₈ClN	F(000) = 672
M_r = 319.81	D_x = 1.339 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 18030 reflections
a = 5.5354 (4) Å	θ = 2.3–26.4°
b = 8.0039 (4) Å	µ = 0.24 mm⁻¹
c = 35.8207 (17) Å	T = 173 K
V = 1587.03 (16) Å³	Plate, colourless
Z = 4	0.35 × 0.21 × 0.11 mm

Data collection top

STOE IPDS II two-circle- diffractometer	3071 independent reflections
Radiation source: fine-focus sealed tube	2867 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
ω scans	θ_max = 25.9°, θ_min = 2.3°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −6→6
T_min = 0.921, T_max = 0.984	k = −9→9
18042 measured reflections	l = −43→44

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.030	w = 1/[σ²(F_o²) + (0.0482P)² + 0.1208P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.079	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.21 e Å⁻³
3071 reflections	Δρ_min = −0.18 e Å⁻³
213 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.026 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1240 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.01 (5)

Crystal data top

C₂₁H₁₈ClN	V = 1587.03 (16) Å³
M_r = 319.81	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.5354 (4) Å	µ = 0.24 mm⁻¹
b = 8.0039 (4) Å	T = 173 K
c = 35.8207 (17) Å	0.35 × 0.21 × 0.11 mm

Data collection top

STOE IPDS II two-circle- diffractometer	3071 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	2867 reflections with I > 2σ(I)
T_min = 0.921, T_max = 0.984	R_int = 0.059
18042 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.079	Δρ_max = 0.21 e Å⁻³
S = 1.05	Δρ_min = −0.18 e Å⁻³
3071 reflections	Absolute structure: Flack (1983), 1240 Friedel pairs
213 parameters	Absolute structure parameter: 0.01 (5)
0 restraints

Special details top

Experimental. ;

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
Cl1	0.19210 (10)	0.59051 (5)	0.005768 (11)	0.04965 (15)
N1	0.1122 (3)	0.01504 (19)	0.06517 (4)	0.0428 (4)
H1	−0.002 (5)	0.000 (3)	0.0477 (7)	0.059 (6)*
C2	0.1862 (4)	−0.12356 (19)	0.08883 (4)	0.0407 (4)
H2A	0.1373	−0.2302	0.0771	0.049*
H2B	0.1034	−0.1151	0.1133	0.049*
C3	0.4575 (4)	−0.12319 (19)	0.09483 (5)	0.0406 (4)
H3A	0.5403	−0.1469	0.0709	0.049*
H3B	0.5017	−0.2120	0.1128	0.049*
C4	0.5406 (3)	0.04765 (18)	0.10990 (4)	0.0317 (3)
H4	0.7213	0.0481	0.1100	0.038*
C5	0.4573 (3)	0.18288 (17)	0.08315 (4)	0.0281 (3)
C6	0.2442 (3)	0.15963 (19)	0.06229 (4)	0.0308 (3)
C7	0.1654 (3)	0.28714 (19)	0.03814 (4)	0.0331 (3)
H7	0.0211	0.2739	0.0241	0.040*
C8	0.3000 (3)	0.43151 (18)	0.03507 (4)	0.0337 (3)
C9	0.5160 (3)	0.45488 (18)	0.05393 (4)	0.0349 (3)
H9	0.6092	0.5534	0.0506	0.042*
C10	0.5906 (3)	0.32869 (19)	0.07781 (4)	0.0327 (3)
H10	0.7381	0.3421	0.0910	0.039*
C11	0.4564 (3)	0.07013 (17)	0.15017 (4)	0.0277 (3)
C12	0.5861 (3)	−0.00906 (19)	0.17846 (4)	0.0319 (3)
H12	0.7295	−0.0682	0.1723	0.038*
C13	0.5108 (3)	−0.00350 (18)	0.21525 (4)	0.0311 (3)
H13	0.6035	−0.0590	0.2338	0.037*
C14	0.3006 (3)	0.08229 (16)	0.22576 (4)	0.0248 (3)
C15	0.1743 (3)	0.16460 (19)	0.19743 (4)	0.0304 (3)
H15	0.0325	0.2257	0.2035	0.037*
C16	0.2518 (3)	0.15902 (19)	0.16041 (4)	0.0310 (3)
H16	0.1628	0.2172	0.1418	0.037*
C21	0.2160 (3)	0.08270 (16)	0.26536 (4)	0.0249 (3)
C22	0.3477 (3)	0.00061 (19)	0.29322 (4)	0.0351 (4)
H22	0.4934	−0.0551	0.2868	0.042*
C23	0.2701 (3)	−0.0012 (2)	0.33005 (4)	0.0403 (4)
H23	0.3632	−0.0577	0.3484	0.048*
C24	0.0585 (3)	0.07846 (19)	0.34030 (4)	0.0357 (4)
H24	0.0048	0.0762	0.3655	0.043*
C25	−0.0739 (3)	0.1618 (2)	0.31320 (5)	0.0371 (4)
H25	−0.2188	0.2178	0.3199	0.045*
C26	0.0041 (3)	0.16382 (19)	0.27635 (4)	0.0321 (3)
H26	−0.0888	0.2217	0.2582	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0746 (3)	0.0413 (2)	0.0330 (2)	0.0169 (2)	0.0022 (2)	0.00881 (16)
N1	0.0445 (8)	0.0444 (8)	0.0394 (8)	−0.0146 (7)	−0.0043 (7)	0.0067 (6)
C2	0.0615 (11)	0.0297 (7)	0.0309 (8)	−0.0111 (8)	0.0079 (8)	−0.0035 (6)
C3	0.0623 (11)	0.0287 (8)	0.0309 (8)	0.0079 (8)	0.0097 (8)	−0.0005 (6)
C4	0.0329 (7)	0.0325 (7)	0.0296 (7)	0.0056 (6)	0.0058 (6)	0.0022 (6)
C5	0.0316 (8)	0.0290 (7)	0.0237 (7)	0.0038 (6)	0.0040 (6)	−0.0007 (5)
C6	0.0341 (8)	0.0337 (7)	0.0246 (7)	−0.0020 (6)	0.0060 (6)	−0.0018 (5)
C7	0.0337 (8)	0.0420 (8)	0.0237 (7)	0.0033 (7)	0.0008 (6)	−0.0011 (6)
C8	0.0473 (9)	0.0304 (7)	0.0235 (7)	0.0083 (7)	0.0045 (7)	0.0002 (5)
C9	0.0461 (9)	0.0271 (7)	0.0315 (7)	−0.0031 (7)	0.0041 (7)	−0.0018 (6)
C10	0.0351 (8)	0.0345 (7)	0.0284 (7)	−0.0023 (6)	0.0025 (6)	−0.0044 (6)
C11	0.0301 (7)	0.0250 (6)	0.0280 (7)	−0.0008 (6)	0.0016 (6)	0.0003 (6)
C12	0.0287 (7)	0.0335 (8)	0.0336 (8)	0.0093 (6)	0.0012 (6)	0.0005 (6)
C13	0.0312 (7)	0.0327 (7)	0.0294 (7)	0.0073 (6)	−0.0046 (6)	0.0016 (6)
C14	0.0253 (6)	0.0214 (6)	0.0278 (6)	−0.0025 (6)	−0.0017 (6)	−0.0012 (5)
C15	0.0278 (7)	0.0329 (7)	0.0306 (7)	0.0083 (6)	0.0009 (6)	−0.0003 (6)
C16	0.0312 (8)	0.0334 (7)	0.0285 (7)	0.0079 (6)	−0.0021 (6)	0.0037 (6)
C21	0.0281 (7)	0.0201 (6)	0.0266 (6)	−0.0038 (6)	−0.0018 (5)	−0.0023 (5)
C22	0.0377 (8)	0.0345 (8)	0.0330 (8)	0.0069 (7)	0.0011 (7)	0.0025 (6)
C23	0.0523 (10)	0.0389 (8)	0.0296 (8)	0.0077 (7)	−0.0025 (7)	0.0058 (6)
C24	0.0491 (9)	0.0307 (7)	0.0273 (7)	−0.0037 (7)	0.0057 (7)	−0.0027 (6)
C25	0.0374 (9)	0.0396 (8)	0.0344 (8)	0.0023 (7)	0.0045 (7)	−0.0068 (7)
C26	0.0317 (8)	0.0345 (7)	0.0302 (7)	0.0036 (7)	−0.0027 (6)	−0.0013 (6)

Geometric parameters (Å, º) top

Cl1—C8	1.7545 (15)	C11—C16	1.387 (2)
N1—C6	1.372 (2)	C11—C12	1.394 (2)
N1—C2	1.455 (2)	C12—C13	1.383 (2)
N1—H1	0.90 (3)	C12—H12	0.9500
C2—C3	1.517 (3)	C13—C14	1.402 (2)
C2—H2A	0.9900	C13—H13	0.9500
C2—H2B	0.9900	C14—C15	1.397 (2)
C3—C4	1.540 (2)	C14—C21	1.4937 (19)
C3—H3A	0.9900	C15—C16	1.395 (2)
C3—H3B	0.9900	C15—H15	0.9500
C4—C5	1.5175 (19)	C16—H16	0.9500
C4—C11	1.5267 (19)	C21—C26	1.398 (2)
C4—H4	1.0000	C21—C22	1.399 (2)
C5—C10	1.394 (2)	C22—C23	1.388 (2)
C5—C6	1.409 (2)	C22—H22	0.9500
C6—C7	1.407 (2)	C23—C24	1.383 (2)
C7—C8	1.379 (2)	C23—H23	0.9500
C7—H7	0.9500	C24—C25	1.387 (2)
C8—C9	1.386 (2)	C24—H24	0.9500
C9—C10	1.386 (2)	C25—C26	1.389 (2)
C9—H9	0.9500	C25—H25	0.9500
C10—H10	0.9500	C26—H26	0.9500

C6—N1—C2	122.48 (15)	C5—C10—H10	118.8
C6—N1—H1	115.7 (15)	C16—C11—C12	117.50 (13)
C2—N1—H1	120.3 (15)	C16—C11—C4	124.03 (13)
N1—C2—C3	111.07 (14)	C12—C11—C4	118.41 (13)
N1—C2—H2A	109.4	C13—C12—C11	121.50 (13)
C3—C2—H2A	109.4	C13—C12—H12	119.2
N1—C2—H2B	109.4	C11—C12—H12	119.2
C3—C2—H2B	109.4	C12—C13—C14	121.44 (13)
H2A—C2—H2B	108.0	C12—C13—H13	119.3
C2—C3—C4	110.31 (13)	C14—C13—H13	119.3
C2—C3—H3A	109.6	C15—C14—C13	116.80 (13)
C4—C3—H3A	109.6	C15—C14—C21	122.13 (12)
C2—C3—H3B	109.6	C13—C14—C21	121.06 (12)
C4—C3—H3B	109.6	C16—C15—C14	121.43 (13)
H3A—C3—H3B	108.1	C16—C15—H15	119.3
C5—C4—C11	114.82 (12)	C14—C15—H15	119.3
C5—C4—C3	108.73 (13)	C11—C16—C15	121.28 (13)
C11—C4—C3	110.15 (12)	C11—C16—H16	119.4
C5—C4—H4	107.6	C15—C16—H16	119.4
C11—C4—H4	107.6	C26—C21—C22	117.03 (13)
C3—C4—H4	107.6	C26—C21—C14	122.11 (12)
C10—C5—C6	118.75 (14)	C22—C21—C14	120.86 (13)
C10—C5—C4	121.53 (14)	C23—C22—C21	121.44 (15)
C6—C5—C4	119.69 (13)	C23—C22—H22	119.3
N1—C6—C7	119.52 (15)	C21—C22—H22	119.3
N1—C6—C5	121.15 (14)	C24—C23—C22	120.65 (15)
C7—C6—C5	119.33 (14)	C24—C23—H23	119.7
C8—C7—C6	119.28 (14)	C22—C23—H23	119.7
C8—C7—H7	120.4	C23—C24—C25	118.89 (14)
C6—C7—H7	120.4	C23—C24—H24	120.6
C7—C8—C9	122.71 (14)	C25—C24—H24	120.6
C7—C8—Cl1	118.13 (13)	C24—C25—C26	120.44 (15)
C9—C8—Cl1	119.17 (12)	C24—C25—H25	119.8
C8—C9—C10	117.34 (14)	C26—C25—H25	119.8
C8—C9—H9	121.3	C25—C26—C21	121.54 (14)
C10—C9—H9	121.3	C25—C26—H26	119.2
C9—C10—C5	122.47 (15)	C21—C26—H26	119.2
C9—C10—H10	118.8

C6—N1—C2—C3	−25.4 (2)	C5—C4—C11—C12	−157.97 (14)
N1—C2—C3—C4	54.08 (17)	C3—C4—C11—C12	78.90 (17)
C2—C3—C4—C5	−55.71 (17)	C16—C11—C12—C13	1.8 (2)
C2—C3—C4—C11	70.92 (17)	C4—C11—C12—C13	−175.56 (15)
C11—C4—C5—C10	88.01 (17)	C11—C12—C13—C14	−0.1 (2)
C3—C4—C5—C10	−148.10 (14)	C12—C13—C14—C15	−1.3 (2)
C11—C4—C5—C6	−93.87 (16)	C12—C13—C14—C21	177.88 (14)
C3—C4—C5—C6	30.02 (18)	C13—C14—C15—C16	1.1 (2)
C2—N1—C6—C7	178.40 (14)	C21—C14—C15—C16	−178.13 (13)
C2—N1—C6—C5	−1.7 (2)	C12—C11—C16—C15	−2.0 (2)
C10—C5—C6—N1	176.93 (14)	C4—C11—C16—C15	175.14 (14)
C4—C5—C6—N1	−1.2 (2)	C14—C15—C16—C11	0.6 (2)
C10—C5—C6—C7	−3.2 (2)	C15—C14—C21—C26	0.8 (2)
C4—C5—C6—C7	178.64 (13)	C13—C14—C21—C26	−178.40 (13)
N1—C6—C7—C8	−179.37 (14)	C15—C14—C21—C22	−179.32 (14)
C5—C6—C7—C8	0.7 (2)	C13—C14—C21—C22	1.5 (2)
C6—C7—C8—C9	2.3 (2)	C26—C21—C22—C23	0.5 (2)
C6—C7—C8—Cl1	−178.17 (11)	C14—C21—C22—C23	−179.43 (14)
C7—C8—C9—C10	−2.6 (2)	C21—C22—C23—C24	0.1 (2)
Cl1—C8—C9—C10	177.80 (11)	C22—C23—C24—C25	−0.6 (2)
C8—C9—C10—C5	0.0 (2)	C23—C24—C25—C26	0.5 (2)
C6—C5—C10—C9	2.8 (2)	C24—C25—C26—C21	0.1 (2)
C4—C5—C10—C9	−179.01 (14)	C22—C21—C26—C25	−0.6 (2)
C5—C4—C11—C16	24.9 (2)	C14—C21—C26—C25	179.31 (14)
C3—C4—C11—C16	−98.23 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1ⁱ	0.90 (3)	2.66 (3)	3.5466 (17)	171 (2)

Symmetry code: (i) x−1/2, −y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₈ClN
M_r	319.81
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	173
a, b, c (Å)	5.5354 (4), 8.0039 (4), 35.8207 (17)
V (Å³)	1587.03 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.35 × 0.21 × 0.11

Data collection
Diffractometer	STOE IPDS II two-circle- diffractometer
Absorption correction	Multi-scan (MULABS; Spek, 2009; Blessing, 1995)
T_min, T_max	0.921, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	18042, 3071, 2867
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.079, 1.05
No. of reflections	3071
No. of parameters	213
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.18
Absolute structure	Flack (1983), 1240 Friedel pairs
Absolute structure parameter	0.01 (5)

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1ⁱ	0.90 (3)	2.66 (3)	3.5466 (17)	171 (2)

Symmetry code: (i) x−1/2, −y+1/2, −z.

References

Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Rueping, M., Dufour, J. & Schoepke, F. R. (2011). Green Chem. 13, 1084–1105. Web of Science CrossRef CAS Google Scholar
Rueping, M., Stoeckel, M., Sugiono, E. & Theissmann, T. (2010). Tetrahedron, 66, 6565–6568. Web of Science CrossRef CAS Google Scholar
Rueping, M., Sugiono, E. & Schoepke, F. R. (2010). Synlett, pp. 852–865. Web of Science CrossRef Google Scholar
Rueping, M., Theissmann, T., Raja, S. & Bats, J. B. (2008). Adv. Synth. Catal. 350, 1001–1006. Web of Science CrossRef CAS Google Scholar
Rueping, M., Theissmann, T., Stoeckel, M. & Antonchick, A. P. (2011). Org. Biomol. Chem. 9, 6844–6850 Web of Science CSD CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar

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