12-Chloro-6-cyclo-hexyl-5,6,7,12-tetra-hydro-dibenzo[c,f][1,5]aza-stibocine.

In the title organometallic complex, [Sb(C(20)H(23)N)Cl], the central anti-mony-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 inter-action exists between the Sb and N atoms on 1,5-aza-stibocine. Inter-molecular 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 = 434.59

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.092

S = 1.05

3644 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.78 e Å−3

Δρmin = −0.55 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811021477/vm2099sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811021477/vm2099Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Sb(C20H23N)Cl]	F(000) = 872
Mr = 434.59	Dx = 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

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

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(Fo2) + (0.0544P)2 + 0.1065P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.020
3644 reflections	Δρmax = 0.78 e Å−3
209 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .