12-Chloro-6-cyclo­hexyl-5,6,7,12-tetra­hydro­dibenzo[c,f][1,5]aza­stibocine

Yi, W.; Tan, N.

doi:10.1107/S1600536811021477

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m917

doi:10.1107/S1600536811021477

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12-Chloro-6-cyclohexyl-5,6,7,12-tetrahydrodibenzo[c,f][1,5]azastibocine

Weiguo Yi ^a ^* and Nianyuan Tan ^b ^*

^aHunan Chemical Vocational Technology College, Zhuzhou 421000, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Hunan Institute of Engineering, Xiangtan 411104, People's Republic of China
^*Correspondence e-mail: ywg6279@126.com, nytan@sina.com

(Received 25 May 2011; accepted 3 June 2011; online 11 June 2011)

In the title organometallic complex, [Sb(C₂₀H₂₃N)Cl], the central antimony-containing part of the complex exhibits a pseudo-trigonal-bipyramidal geometry, where two C atoms and a lone electron pair of the Sb atom exist at the equatorial positions, while the N and Cl atoms are located at the apical positions, and a transannular interaction exists between the Sb and N atoms on 1,5-azastibocine. Intermolecular C—H⋯Cl hydrogen bonds are also observed.

Related literature

For general background, see: Yin et al. (2008 ); Chovancová et al. (2009 ); Opris et al. (2009 ); Svoboda et al. (2010 ); Tan & Zhang (2011 ). For related structures, see: Kakusawa et al. (2006 ); Xia et al. (2010 ).

Experimental

Crystal data

[Sb(C₂₀H₂₃N)Cl]
M_r = 434.59
Monoclinic, P 2₁ /c
a = 10.0771 (7) Å
b = 16.2881 (12) Å
c = 12.2040 (9) Å
β = 111.812 (1)°
V = 1859.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 1.63 mm⁻¹
T = 293 K
0.37 × 0.35 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ) T_min = 0.653, T_max = 1.000
10058 measured reflections
3644 independent reflections
3107 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.092
S = 1.05
3644 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.78 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯Cl1ⁱ	0.97	2.80	3.695 (4)	154
Symmetry code: (i) -x+1, -y+2, -z.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811021477/vm2099sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811021477/vm2099Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811021477/vm2099Isup3.cml

checkCIF report

Comment top

The chemistry of hypervalent compounds bearing heavier pnictogens (in particular Sb, Bi) has been studied intensively in recent years (Yin et al., 2008; Chovancová et al., 2009; Svoboda et al., 2010; Tan & Zhang, 2011). Intramolecular interactions between antimony and sp³-nitrogen atoms have been widely reported (Kakusawa et al., 2006; Opris et al., 2009; Xia et al., 2010). Here, we reported the crystal structure of the title organometallic complex (Fig. 1). The central antimony-containing part of the complex shows a distorted pseudo trigonal-bipyramidal structure. The C1, C8 atoms along with a lone electron pair of the Sb atom exist at the equatorial positions while the N1 and Cl1 atoms are located at the apical positions. The Sb–C1 and Sb–C8 distance is 2.144 (4) Å and 2.134 (3) Å, respectively. The C1–Sb–C8 angle is 98.17 (12)°, while the N1–Sb–Cl1 angle is 162.92 (7)° (rather than 180°). The Sb–N1 distance (2.397 (3) Å) is shorter than the sum of the van der Waals radii of nitrogen and antimony atoms (3.74 Å) (Kakusawa et al., 2006), indicating that coordination exists between the two atoms. The complex also displays intermolecular hydrogen-bonding interaction between the CH₂ groups and chlorine atom Cl1 (Table 1).

Related literature top

For general background, see: Yin et al. (2008); Chovancová et al. (2009); Opris et al. (2009); Svoboda et al. (2010); Tan & Zhang (2011). For related structures, see: Kakusawa et al. (2006); Xia et al. (2010).

Experimental top

N,N-bis(2-bromobenzyl)cyclohexanamine (2.186 g, 5.0 mmol) was allowed to react with n-BuLi (2.5 M, 4.0 ml, 10 mmol) at -50 ^oC, and the resulting solution was added to a mixture of SbCl₃ (1.141 g, 5.0 mmol) in Et₂O (80 ml) at -78 ^oC. The obtained mixture was gradually warmed to room temperature and stirred for 12 h. Then the solvent was removed under vacuum and the residue was extracted with toluene, and the insoluble material was removed by filtration. The organic layer was washed with de-ionized H₂O and dried over anhydrous Na₂SO₄. After the solvent was removed under reduced pressure, the residue was recrystallized from CH₂Cl₂/hexane to obtain the title compound in the form of colorless crystals.

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, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A packing diagram of the title compound viewed down the a axis.

12-Chloro-6-cyclohexyl-5,6,7,12- tetrahydrodibenzo[c,f][1,5]azastibocine top

Crystal data top

[Sb(C₂₀H₂₃N)Cl]	F(000) = 872
M_r = 434.59	D_x = 1.552 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 527.15 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.0771 (7) Å	Cell parameters from 5285 reflections
b = 16.2881 (12) Å	θ = 4.4–55.7°
c = 12.2040 (9) Å	µ = 1.63 mm⁻¹
β = 111.812 (1)°	T = 293 K
V = 1859.7 (2) Å³	Prismatic, colorless
Z = 4	0.37 × 0.35 × 0.21 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3644 independent reflections
Radiation source: fine-focus sealed tube	3107 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 10.00 pixels mm^-1	θ_max = 26.0°, θ_min = 2.2°
ϕ and ω scans	h = −12→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −20→19
T_min = 0.653, T_max = 1.000	l = −15→14
10058 measured reflections

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)] = 0.032	H-atom parameters constrained
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.0544P)² + 0.1065P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.020
3644 reflections	Δρ_max = 0.78 e Å⁻³
209 parameters	Δρ_min = −0.55 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0030 (4)

Crystal data top

[Sb(C₂₀H₂₃N)Cl]	V = 1859.7 (2) Å³
M_r = 434.59	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.0771 (7) Å	µ = 1.63 mm⁻¹
b = 16.2881 (12) Å	T = 293 K
c = 12.2040 (9) Å	0.37 × 0.35 × 0.21 mm
β = 111.812 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3644 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	3107 reflections with I > 2σ(I)
T_min = 0.653, T_max = 1.000	R_int = 0.047
10058 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.05	Δρ_max = 0.78 e Å⁻³
3644 reflections	Δρ_min = −0.55 e Å⁻³
209 parameters

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
Sb	0.38578 (2)	1.037779 (13)	0.117005 (18)	0.04278 (12)
Cl1	0.43763 (12)	1.19188 (5)	0.12783 (8)	0.0597 (3)
N1	0.3869 (3)	0.89526 (15)	0.1662 (2)	0.0400 (6)
C1	0.6082 (4)	1.0063 (2)	0.1912 (3)	0.0459 (8)
C2	0.7215 (5)	1.0616 (3)	0.2281 (4)	0.0615 (10)
H2	0.7033	1.1177	0.2246	0.074*
C3	0.8613 (5)	1.0335 (3)	0.2700 (5)	0.0772 (14)
H3	0.9367	1.0707	0.2947	0.093*
C4	0.8882 (5)	0.9511 (3)	0.2750 (5)	0.0734 (13)
H4	0.9822	0.9324	0.3034	0.088*
C5	0.7772 (4)	0.8953 (3)	0.2383 (4)	0.0647 (11)
H5	0.7968	0.8393	0.2424	0.078*
C6	0.6365 (4)	0.9224 (2)	0.1953 (3)	0.0475 (8)
C7	0.5159 (4)	0.8623 (2)	0.1497 (3)	0.0505 (9)
H7A	0.4943	0.8521	0.0666	0.061*
H7B	0.5436	0.8107	0.1917	0.061*
C8	0.3459 (3)	1.04120 (18)	0.2769 (3)	0.0405 (7)
C9	0.3038 (4)	1.1103 (2)	0.3214 (3)	0.0544 (9)
H9	0.2980	1.1605	0.2836	0.065*
C10	0.2703 (4)	1.1057 (3)	0.4213 (4)	0.0662 (11)
H10	0.2449	1.1530	0.4515	0.079*
C11	0.2746 (4)	1.0317 (3)	0.4757 (4)	0.0641 (11)
H11	0.2484	1.0286	0.5410	0.077*
C12	0.3175 (4)	0.9621 (2)	0.4344 (3)	0.0530 (10)
H12	0.3233	0.9124	0.4733	0.064*
C13	0.3522 (3)	0.96613 (19)	0.3339 (3)	0.0413 (7)
C14	0.4045 (4)	0.89040 (19)	0.2921 (3)	0.0445 (7)
H14A	0.5048	0.8823	0.3398	0.053*
H14B	0.3523	0.8431	0.3033	0.053*
C15	0.2520 (4)	0.8556 (2)	0.0804 (3)	0.0546 (9)
H15	0.2451	0.8713	0.0009	0.066*
C16	0.2535 (5)	0.7640 (2)	0.0841 (5)	0.0772 (13)
H16A	0.2598	0.7455	0.1615	0.093*
H16B	0.3362	0.7435	0.0702	0.093*
C17	0.1141 (5)	0.7300 (3)	−0.0122 (5)	0.1008 (18)
H17A	0.1129	0.7441	−0.0898	0.121*
H17B	0.1127	0.6706	−0.0065	0.121*
C18	−0.0157 (5)	0.7648 (3)	0.0023 (5)	0.0968 (17)
H18A	−0.1006	0.7448	−0.0607	0.116*
H18B	−0.0193	0.7461	0.0767	0.116*
C19	−0.0150 (5)	0.8545 (3)	0.0004 (5)	0.0885 (15)
H19A	−0.0989	0.8749	0.0125	0.106*
H19B	−0.0197	0.8731	−0.0765	0.106*
C20	0.1202 (4)	0.8898 (2)	0.0964 (4)	0.0636 (10)
H20A	0.1197	0.9492	0.0907	0.076*
H20B	0.1217	0.8751	0.1739	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sb	0.05674 (19)	0.03541 (16)	0.03702 (16)	0.00115 (9)	0.01840 (11)	−0.00007 (8)
Cl1	0.0872 (7)	0.0321 (4)	0.0647 (6)	−0.0061 (4)	0.0338 (5)	−0.0033 (4)
N1	0.0432 (15)	0.0373 (14)	0.0405 (14)	0.0032 (11)	0.0168 (11)	−0.0007 (11)
C1	0.051 (2)	0.0490 (19)	0.0467 (19)	−0.0022 (16)	0.0285 (16)	−0.0007 (15)
C2	0.067 (3)	0.059 (2)	0.067 (3)	−0.007 (2)	0.035 (2)	−0.007 (2)
C3	0.057 (3)	0.096 (4)	0.084 (3)	−0.022 (2)	0.032 (2)	−0.017 (3)
C4	0.051 (2)	0.095 (4)	0.081 (3)	0.005 (2)	0.034 (2)	−0.002 (3)
C5	0.058 (2)	0.075 (3)	0.069 (3)	0.009 (2)	0.033 (2)	0.001 (2)
C6	0.053 (2)	0.050 (2)	0.048 (2)	0.0037 (16)	0.0287 (16)	0.0017 (15)
C7	0.061 (2)	0.0412 (18)	0.059 (2)	0.0029 (16)	0.0332 (18)	−0.0030 (16)
C8	0.0390 (17)	0.0445 (18)	0.0372 (17)	0.0020 (13)	0.0134 (13)	−0.0059 (13)
C9	0.053 (2)	0.058 (2)	0.050 (2)	0.0065 (17)	0.0155 (16)	−0.0105 (16)
C10	0.056 (2)	0.084 (3)	0.061 (3)	0.010 (2)	0.0237 (19)	−0.026 (2)
C11	0.056 (2)	0.094 (3)	0.049 (2)	−0.003 (2)	0.0279 (19)	−0.015 (2)
C12	0.044 (2)	0.076 (3)	0.040 (2)	−0.0035 (16)	0.0162 (16)	0.0037 (16)
C13	0.0347 (17)	0.052 (2)	0.0355 (17)	−0.0007 (13)	0.0118 (13)	−0.0021 (13)
C14	0.0472 (18)	0.0436 (18)	0.0433 (18)	0.0026 (14)	0.0177 (14)	0.0068 (14)
C15	0.057 (2)	0.0428 (19)	0.059 (2)	−0.0008 (16)	0.0163 (18)	−0.0080 (16)
C16	0.069 (3)	0.048 (2)	0.105 (4)	−0.0050 (19)	0.020 (2)	−0.012 (2)
C17	0.085 (4)	0.065 (3)	0.131 (5)	−0.017 (3)	0.016 (3)	−0.041 (3)
C18	0.066 (3)	0.080 (3)	0.128 (5)	−0.020 (3)	0.018 (3)	−0.021 (3)
C19	0.062 (3)	0.076 (3)	0.106 (4)	−0.004 (2)	0.007 (3)	−0.016 (3)
C20	0.051 (2)	0.057 (2)	0.075 (3)	−0.0014 (18)	0.0144 (19)	−0.0096 (19)

Geometric parameters (Å, º) top

Sb—C8	2.134 (3)	C10—H10	0.9300
Sb—C1	2.144 (4)	C11—C12	1.374 (5)
Sb—N1	2.397 (3)	C11—H11	0.9300
Sb—Cl1	2.5573 (9)	C12—C13	1.396 (5)
N1—C14	1.481 (4)	C12—H12	0.9300
N1—C7	1.487 (4)	C13—C14	1.503 (4)
N1—C15	1.518 (4)	C14—H14A	0.9700
C1—C2	1.391 (5)	C14—H14B	0.9700
C1—C6	1.393 (5)	C15—C16	1.493 (5)
C2—C3	1.385 (6)	C15—C20	1.518 (5)
C2—H2	0.9300	C15—H15	0.9800
C3—C4	1.367 (6)	C16—C17	1.560 (6)
C3—H3	0.9300	C16—H16A	0.9700
C4—C5	1.381 (6)	C16—H16B	0.9700
C4—H4	0.9300	C17—C18	1.495 (7)
C5—C6	1.389 (5)	C17—H17A	0.9700
C5—H5	0.9300	C17—H17B	0.9700
C6—C7	1.497 (5)	C18—C19	1.462 (6)
C7—H7A	0.9700	C18—H18A	0.9700
C7—H7B	0.9700	C18—H18B	0.9700
C8—C9	1.383 (4)	C19—C20	1.541 (6)
C8—C13	1.397 (4)	C19—H19A	0.9700
C9—C10	1.382 (6)	C19—H19B	0.9700
C9—H9	0.9300	C20—H20A	0.9700
C10—C11	1.369 (6)	C20—H20B	0.9700

C8—Sb—C1	98.17 (12)	C11—C12—C13	119.9 (4)
C8—Sb—N1	77.37 (10)	C11—C12—H12	120.0
C1—Sb—N1	75.86 (11)	C13—C12—H12	120.0
C8—Sb—Cl1	91.80 (8)	C8—C13—C12	119.9 (3)
C1—Sb—Cl1	92.95 (10)	C8—C13—C14	120.4 (3)
N1—Sb—Cl1	162.92 (7)	C12—C13—C14	119.6 (3)
C14—N1—C7	110.3 (3)	N1—C14—C13	112.7 (3)
C14—N1—C15	115.1 (3)	N1—C14—H14A	109.0
C7—N1—C15	110.9 (3)	C13—C14—H14A	109.0
C14—N1—Sb	107.40 (18)	N1—C14—H14B	109.0
C7—N1—Sb	103.79 (19)	C13—C14—H14B	109.0
C15—N1—Sb	108.64 (19)	H14A—C14—H14B	107.8
C2—C1—C6	119.4 (4)	C16—C15—C20	111.2 (3)
C2—C1—Sb	125.8 (3)	C16—C15—N1	114.1 (3)
C6—C1—Sb	114.7 (2)	C20—C15—N1	110.9 (3)
C3—C2—C1	120.4 (4)	C16—C15—H15	106.7
C3—C2—H2	119.8	C20—C15—H15	106.7
C1—C2—H2	119.8	N1—C15—H15	106.7
C4—C3—C2	119.9 (4)	C15—C16—C17	109.6 (4)
C4—C3—H3	120.0	C15—C16—H16A	109.7
C2—C3—H3	120.0	C17—C16—H16A	109.7
C3—C4—C5	120.6 (4)	C15—C16—H16B	109.7
C3—C4—H4	119.7	C17—C16—H16B	109.7
C5—C4—H4	119.7	H16A—C16—H16B	108.2
C4—C5—C6	120.2 (4)	C18—C17—C16	111.0 (4)
C4—C5—H5	119.9	C18—C17—H17A	109.4
C6—C5—H5	119.9	C16—C17—H17A	109.4
C5—C6—C1	119.5 (3)	C18—C17—H17B	109.4
C5—C6—C7	120.4 (3)	C16—C17—H17B	109.4
C1—C6—C7	120.0 (3)	H17A—C17—H17B	108.0
N1—C7—C6	110.1 (3)	C19—C18—C17	111.5 (4)
N1—C7—H7A	109.6	C19—C18—H18A	109.3
C6—C7—H7A	109.6	C17—C18—H18A	109.3
N1—C7—H7B	109.6	C19—C18—H18B	109.3
C6—C7—H7B	109.6	C17—C18—H18B	109.3
H7A—C7—H7B	108.2	H18A—C18—H18B	108.0
C9—C8—C13	118.7 (3)	C18—C19—C20	111.6 (4)
C9—C8—Sb	124.7 (3)	C18—C19—H19A	109.3
C13—C8—Sb	116.3 (2)	C20—C19—H19A	109.3
C10—C9—C8	120.9 (4)	C18—C19—H19B	109.3
C10—C9—H9	119.5	C20—C19—H19B	109.3
C8—C9—H9	119.5	H19A—C19—H19B	108.0
C11—C10—C9	120.0 (4)	C15—C20—C19	109.5 (4)
C11—C10—H10	120.0	C15—C20—H20A	109.8
C9—C10—H10	120.0	C19—C20—H20A	109.8
C10—C11—C12	120.4 (4)	C15—C20—H20B	109.8
C10—C11—H11	119.8	C19—C20—H20B	109.8
C12—C11—H11	119.8	H20A—C20—H20B	108.2

C8—Sb—N1—C14	−17.0 (2)	C1—Sb—C8—C13	−68.2 (3)
C1—Sb—N1—C14	84.9 (2)	N1—Sb—C8—C13	5.3 (2)
Cl1—Sb—N1—C14	34.7 (4)	Cl1—Sb—C8—C13	−161.4 (2)
C8—Sb—N1—C7	−133.8 (2)	C13—C8—C9—C10	0.8 (5)
C1—Sb—N1—C7	−31.9 (2)	Sb—C8—C9—C10	175.3 (3)
Cl1—Sb—N1—C7	−82.1 (3)	C8—C9—C10—C11	−1.9 (6)
C8—Sb—N1—C15	108.1 (2)	C9—C10—C11—C12	2.6 (6)
C1—Sb—N1—C15	−150.0 (2)	C10—C11—C12—C13	−2.2 (6)
Cl1—Sb—N1—C15	159.8 (2)	C9—C8—C13—C12	−0.5 (5)
C8—Sb—C1—C2	−91.1 (3)	Sb—C8—C13—C12	−175.4 (3)
N1—Sb—C1—C2	−165.8 (3)	C9—C8—C13—C14	−176.9 (3)
Cl1—Sb—C1—C2	1.2 (3)	Sb—C8—C13—C14	8.2 (4)
C8—Sb—C1—C6	92.5 (2)	C11—C12—C13—C8	1.2 (5)
N1—Sb—C1—C6	17.8 (2)	C11—C12—C13—C14	177.6 (3)
Cl1—Sb—C1—C6	−175.2 (2)	C7—N1—C14—C13	137.9 (3)
C6—C1—C2—C3	−0.9 (6)	C15—N1—C14—C13	−95.7 (3)
Sb—C1—C2—C3	−177.2 (3)	Sb—N1—C14—C13	25.4 (3)
C1—C2—C3—C4	0.1 (7)	C8—C13—C14—N1	−24.4 (4)
C2—C3—C4—C5	0.2 (8)	C12—C13—C14—N1	159.2 (3)
C3—C4—C5—C6	0.3 (7)	C14—N1—C15—C16	−72.1 (4)
C4—C5—C6—C1	−1.0 (6)	C7—N1—C15—C16	54.0 (4)
C4—C5—C6—C7	176.9 (4)	Sb—N1—C15—C16	167.5 (3)
C2—C1—C6—C5	1.3 (5)	C14—N1—C15—C20	54.4 (4)
Sb—C1—C6—C5	178.0 (3)	C7—N1—C15—C20	−179.5 (3)
C2—C1—C6—C7	−176.6 (3)	Sb—N1—C15—C20	−66.0 (3)
Sb—C1—C6—C7	0.0 (4)	C20—C15—C16—C17	56.9 (5)
C14—N1—C7—C6	−74.4 (3)	N1—C15—C16—C17	−176.8 (4)
C15—N1—C7—C6	156.9 (3)	C15—C16—C17—C18	−55.8 (6)
Sb—N1—C7—C6	40.4 (3)	C16—C17—C18—C19	56.2 (7)
C5—C6—C7—N1	151.3 (3)	C17—C18—C19—C20	−57.1 (7)
C1—C6—C7—N1	−30.7 (4)	C16—C15—C20—C19	−57.3 (5)
C1—Sb—C8—C9	117.3 (3)	N1—C15—C20—C19	174.6 (3)
N1—Sb—C8—C9	−169.3 (3)	C18—C19—C20—C15	57.0 (6)
Cl1—Sb—C8—C9	24.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···Cl1ⁱ	0.97	2.80	3.695 (4)	154

Symmetry code: (i) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	[Sb(C₂₀H₂₃N)Cl]
M_r	434.59
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.0771 (7), 16.2881 (12), 12.2040 (9)
β (°)	111.812 (1)
V (Å³)	1859.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.63
Crystal size (mm)	0.37 × 0.35 × 0.21

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1999)
T_min, T_max	0.653, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10058, 3644, 3107
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.092, 1.05
No. of reflections	3644
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.78, −0.55

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···Cl1ⁱ	0.97	2.80	3.695 (4)	154.3

Symmetry code: (i) −x+1, −y+2, −z.

Acknowledgements

The authors thank the NSFC for financial support (grant No. 21003040).

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