6-Phenyl-6,7-dihydro-dibenzo[c,f][1,5]aza-bis-mocin-12(5H)-yl perchlorate.

In the title compound, [Bi(C(20)H(17)N)(ClO(4))] or C(20)H(17)BiClNO(4), the Bi(III) ion assumes a distorted ψ trigonal-bipyramidal geometry, with two C atoms and the electron lone pair of the Bi atom at the equatorial positions and an amine N atom and a perchlorate O atom at the apical positions. Weak inter-molecular C-H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For the synthesis of 12-chloro-6-phenyl-5,6,7,12-tetra­hydro­dibenzo[c,f][1,5]aza­bis­mocine, see: Zhang et al. (2009 ▶). For general background, see: Shimada et al. (2004 ▶); Yin et al. (2008 ▶); Zhang et al. (2010 ▶); Tan & Zhang (2011 ▶). For related structures, see: Ohkata et al. (1989 ▶); Minoura et al. (1999 ▶).

Experimental

Crystal data

[Bi(C20H17N)(ClO4)]

M = 579.78

Monoclinic,

a = 12.0635 (10) Å

b = 14.0755 (12) Å

c = 11.5121 (10) Å

β = 107.590 (2)°

V = 1863.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 9.63 mm−1

T = 293 K

0.32 × 0.21 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan(SADABS; Bruker, 2001 ▶) T min = 0.100, T max = 0.145

9267 measured reflections

3279 independent reflections

2585 reflections with I > 2σ(I)

R int = 0.166

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.163

S = 1.02

3279 reflections

244 parameters

H-atom parameters constrained

Δρmax = 4.89 e Å−3

Δρmin = −4.14 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811021039/xu5208sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021039/xu5208Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811021039/xu5208Isup3.cml

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

[Bi(C20H17N)(ClO4)]	F(000) = 1104
Mr = 579.78	Dx = 2.067 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2936 reflections
a = 12.0635 (10) Å	θ = 2.7–24.2°
b = 14.0755 (12) Å	µ = 9.63 mm−1
c = 11.5121 (10) Å	T = 293 K
β = 107.590 (2)°	Prismatic, colorless
V = 1863.4 (3) Å3	0.32 × 0.21 × 0.20 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	3279 independent reflections
Radiation source: fine-focus sealed tube	2585 reflections with I > 2σ(I)
graphite	Rint = 0.166
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2001)	h = −10→14
Tmin = 0.100, Tmax = 0.145	k = −13→16
9267 measured reflections	l = −13→13

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0816P)2] where P = (Fo2 + 2Fc2)/3
3279 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 4.89 e Å−3
0 restraints	Δρmin = −4.14 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Bi	0.74646 (4)	0.77309 (3)	0.84604 (4)	0.0321 (2)
Cl1	0.7240 (3)	1.0213 (2)	0.8825 (3)	0.0378 (7)
N1	0.7225 (7)	0.6171 (8)	0.7606 (7)	0.033 (2)
O1	0.7940 (9)	0.9494 (7)	0.8480 (10)	0.063 (3)
O2	0.6291 (9)	0.9730 (7)	0.9075 (10)	0.069 (3)
O3	0.6836 (10)	1.0854 (8)	0.7850 (10)	0.071 (3)
O4	0.7937 (12)	1.0687 (8)	0.9874 (10)	0.086 (4)
C1	0.6226 (11)	0.7895 (8)	0.6574 (11)	0.037 (3)
C2	0.6002 (10)	0.8714 (8)	0.5878 (10)	0.034 (3)
H2	0.6373	0.9281	0.6181	0.041*
C3	0.5204 (11)	0.8671 (9)	0.4706 (11)	0.041 (3)
H3	0.5026	0.9222	0.4241	0.049*
C4	0.4688 (12)	0.7846 (8)	0.4240 (12)	0.042 (3)
H4	0.4163	0.7830	0.3459	0.051*
C5	0.4949 (11)	0.7005 (9)	0.4943 (11)	0.037 (3)
H5	0.4603	0.6435	0.4617	0.045*
C6	0.5695 (10)	0.7026 (9)	0.6080 (10)	0.033 (3)
C7	0.5996 (10)	0.6133 (8)	0.6827 (9)	0.031 (3)
H7A	0.5489	0.6068	0.7335	0.037*
H7B	0.5881	0.5586	0.6292	0.037*
C8	0.8978 (11)	0.7594 (8)	0.7776 (11)	0.030 (3)
C9	0.9896 (11)	0.8252 (10)	0.7942 (12)	0.047 (3)
H9	0.9914	0.8787	0.8421	0.056*
C10	1.0741 (11)	0.8122 (10)	0.7424 (14)	0.051 (4)
H10	1.1337	0.8565	0.7542	0.062*
C11	1.0723 (14)	0.7321 (10)	0.6709 (16)	0.055 (4)
H11	1.1291	0.7246	0.6321	0.066*
C12	0.9893 (10)	0.6651 (9)	0.6570 (11)	0.038 (3)
H12	0.9919	0.6101	0.6132	0.045*
C13	0.8986 (9)	0.6785 (8)	0.7091 (9)	0.030 (2)
C14	0.8015 (10)	0.6065 (8)	0.6812 (10)	0.033 (3)
H14A	0.8350	0.5433	0.6923	0.040*
H14B	0.7555	0.6128	0.5965	0.040*
C15	0.7472 (9)	0.5399 (9)	0.8534 (10)	0.033 (3)
C16	0.6852 (11)	0.4552 (9)	0.8367 (12)	0.041 (3)
H16	0.6240	0.4455	0.7659	0.049*
C17	0.7139 (13)	0.3865 (10)	0.9238 (14)	0.053 (4)
H17	0.6723	0.3298	0.9117	0.064*
C18	0.8062 (14)	0.4002 (11)	1.0325 (14)	0.058 (4)
H18	0.8251	0.3532	1.0919	0.069*
C19	0.8671 (14)	0.4831 (12)	1.0489 (13)	0.064 (4)
H19	0.9281	0.4920	1.1202	0.077*
C20	0.8408 (11)	0.5534 (11)	0.9634 (11)	0.050 (3)
H20	0.8833	0.6097	0.9763	0.060*

	U11	U22	U33	U12	U13	U23
Bi	0.0313 (3)	0.0438 (3)	0.0201 (3)	0.00040 (18)	0.0062 (2)	−0.00470 (18)
Cl1	0.0407 (17)	0.0414 (16)	0.0248 (14)	0.0024 (13)	0.0001 (12)	0.0037 (13)
N1	0.018 (5)	0.070 (7)	0.007 (4)	0.002 (4)	−0.001 (4)	0.001 (4)
O1	0.047 (6)	0.064 (7)	0.079 (8)	0.005 (5)	0.020 (5)	−0.009 (6)
O2	0.054 (6)	0.076 (7)	0.086 (8)	0.001 (5)	0.036 (6)	0.026 (6)
O3	0.082 (8)	0.065 (7)	0.059 (7)	0.000 (6)	0.008 (6)	0.034 (6)
O4	0.122 (11)	0.076 (8)	0.035 (6)	−0.017 (7)	−0.015 (6)	−0.011 (6)
C1	0.038 (7)	0.045 (7)	0.033 (7)	0.005 (5)	0.016 (6)	−0.005 (6)
C2	0.041 (7)	0.038 (6)	0.025 (6)	0.005 (5)	0.012 (5)	0.003 (5)
C3	0.043 (7)	0.053 (8)	0.032 (7)	0.013 (6)	0.019 (6)	0.013 (6)
C4	0.044 (8)	0.049 (8)	0.030 (7)	0.006 (6)	0.006 (6)	−0.004 (6)
C5	0.034 (7)	0.050 (8)	0.022 (6)	0.002 (5)	−0.002 (5)	−0.008 (5)
C6	0.021 (6)	0.054 (7)	0.025 (6)	0.000 (5)	0.006 (5)	0.007 (5)
C7	0.033 (6)	0.036 (6)	0.020 (5)	−0.006 (5)	0.003 (5)	0.004 (5)
C8	0.030 (7)	0.038 (6)	0.027 (6)	0.001 (5)	0.015 (5)	0.003 (5)
C9	0.045 (8)	0.045 (8)	0.048 (8)	−0.013 (6)	0.010 (6)	−0.015 (7)
C10	0.031 (7)	0.058 (8)	0.066 (9)	−0.013 (6)	0.015 (7)	0.005 (8)
C11	0.051 (10)	0.066 (10)	0.058 (10)	0.007 (7)	0.030 (8)	0.012 (8)
C12	0.035 (7)	0.046 (7)	0.034 (6)	0.004 (5)	0.012 (5)	−0.003 (6)
C13	0.031 (6)	0.039 (6)	0.020 (5)	0.002 (5)	0.006 (5)	0.003 (5)
C14	0.034 (6)	0.042 (7)	0.026 (6)	−0.001 (5)	0.014 (5)	−0.003 (5)
C15	0.036 (7)	0.036 (7)	0.030 (6)	0.004 (5)	0.015 (5)	0.006 (5)
C16	0.038 (7)	0.045 (8)	0.039 (7)	0.005 (6)	0.010 (6)	0.010 (6)
C17	0.059 (9)	0.045 (8)	0.063 (9)	0.005 (7)	0.029 (8)	0.020 (7)
C18	0.066 (10)	0.063 (10)	0.050 (9)	0.020 (8)	0.026 (8)	0.024 (8)
C19	0.061 (10)	0.083 (12)	0.041 (8)	0.011 (9)	0.005 (7)	0.018 (8)
C20	0.042 (8)	0.069 (10)	0.027 (7)	0.000 (7)	−0.007 (6)	0.004 (7)

Bi—N1	2.387 (10)	C8—C13	1.387 (17)
Bi—O1	2.546 (10)	C8—C9	1.411 (17)
Bi—C1	2.245 (13)	C9—C10	1.340 (18)
Bi—C8	2.204 (12)	C9—H9	0.9300
Cl1—O3	1.407 (10)	C10—C11	1.39 (2)
Cl1—O4	1.413 (10)	C10—H10	0.9300
Cl1—O2	1.434 (10)	C11—C12	1.349 (19)
Cl1—O1	1.448 (10)	C11—H11	0.9300
N1—C7	1.484 (13)	C12—C13	1.410 (16)
N1—C15	1.490 (15)	C12—H12	0.9300
N1—C14	1.514 (12)	C13—C14	1.508 (15)
C1—C2	1.383 (16)	C14—H14A	0.9700
C1—C6	1.418 (17)	C14—H14B	0.9700
C2—C3	1.402 (17)	C15—C16	1.389 (18)
C2—H2	0.9300	C15—C20	1.432 (16)
C3—C4	1.351 (18)	C16—C17	1.360 (18)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.414 (18)	C17—C18	1.41 (2)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.347 (16)	C18—C19	1.36 (2)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.504 (16)	C19—C20	1.365 (19)
C7—H7A	0.9700	C19—H19	0.9300
C7—H7B	0.9700	C20—H20	0.9300
C8—Bi—C1	92.5 (5)	C13—C8—C9	118.4 (11)
C8—Bi—N1	77.4 (4)	C13—C8—Bi	115.1 (8)
C1—Bi—N1	74.6 (4)	C9—C8—Bi	126.5 (9)
C8—Bi—O1	83.1 (4)	C10—C9—C8	121.5 (13)
C1—Bi—O1	89.4 (4)	C10—C9—H9	119.3
N1—Bi—O1	154.0 (3)	C8—C9—H9	119.3
O3—Cl1—O4	110.7 (7)	C9—C10—C11	119.7 (13)
O3—Cl1—O2	111.0 (7)	C9—C10—H10	120.2
O4—Cl1—O2	110.9 (7)	C11—C10—H10	120.2
O3—Cl1—O1	108.6 (7)	C12—C11—C10	120.9 (13)
O4—Cl1—O1	108.6 (8)	C12—C11—H11	119.5
O2—Cl1—O1	106.9 (6)	C10—C11—H11	119.5
C7—N1—C15	110.7 (9)	C11—C12—C13	120.0 (12)
C7—N1—C14	109.2 (8)	C11—C12—H12	120.0
C15—N1—C14	109.6 (8)	C13—C12—H12	120.0
C7—N1—Bi	104.8 (7)	C8—C13—C12	119.4 (11)
C15—N1—Bi	113.7 (6)	C8—C13—C14	122.3 (10)
C14—N1—Bi	108.6 (7)	C12—C13—C14	118.2 (10)
Cl1—O1—Bi	122.3 (6)	C13—C14—N1	113.3 (9)
C2—C1—C6	120.1 (12)	C13—C14—H14A	108.9
C2—C1—Bi	127.1 (9)	N1—C14—H14A	108.9
C6—C1—Bi	112.7 (8)	C13—C14—H14B	108.9
C1—C2—C3	118.6 (12)	N1—C14—H14B	108.9
C1—C2—H2	120.7	H14A—C14—H14B	107.7
C3—C2—H2	120.7	C16—C15—C20	119.0 (11)
C4—C3—C2	121.3 (12)	C16—C15—N1	123.0 (10)
C4—C3—H3	119.4	C20—C15—N1	118.0 (11)
C2—C3—H3	119.4	C17—C16—C15	120.1 (13)
C3—C4—C5	119.8 (13)	C17—C16—H16	119.9
C3—C4—H4	120.1	C15—C16—H16	119.9
C5—C4—H4	120.1	C16—C17—C18	120.8 (14)
C6—C5—C4	120.4 (12)	C16—C17—H17	119.6
C6—C5—H5	119.8	C18—C17—H17	119.6
C4—C5—H5	119.8	C19—C18—C17	119.2 (13)
C5—C6—C1	119.8 (12)	C19—C18—H18	120.4
C5—C6—C7	120.9 (11)	C17—C18—H18	120.4
C1—C6—C7	119.3 (11)	C18—C19—C20	121.6 (15)
N1—C7—C6	109.9 (9)	C18—C19—H19	119.2
N1—C7—H7A	109.7	C20—C19—H19	119.2
C6—C7—H7A	109.7	C19—C20—C15	119.4 (14)
N1—C7—H7B	109.7	C19—C20—H20	120.3
C6—C7—H7B	109.7	C15—C20—H20	120.3
H7A—C7—H7B	108.2

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3i	0.93	2.46	3.137 (17)	130
C14—H14B···O2ii	0.97	2.55	3.398 (16)	146

Table 1

Selected bond lengths (Å)

Bi—N1	2.387 (10)
Bi—O1	2.546 (10)
Bi—C1	2.245 (13)
Bi—C8	2.204 (12)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O3i	0.93	2.46	3.137 (17)	130
C14—H14B⋯O2ii	0.97	2.55	3.398 (16)	146

Symmetry codes: (i) ; (ii) .