1,1′-(Propane-1,3-diyl)dipyridinium dibromidodichloridocadmate(II)

Liu, X.-C.; Shi, J.; Niu, Y.-Y.; Xu, N.; Ng, S.W.

doi:10.1107/S1600536807025597

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1,1'-(Propane-1,3-diyl)dipyridinium dibromidodichloridocadmate(II)

X.-C. Liu, J. Shi, Y.-Y. Niu, N. Xu and S. W. Ng

The Cd atom in the title compound, (C₁₃H₁₆N₂)[CdBr₂Cl₂], is coordinated by four halogen atoms in a tetrahedral geometry. The four halogen atoms are each disordered between Br and Cl, with the Br:Cl ratios being approximately 0.5:0.5, 0.6:0.4, 0.4:0.6 and 0.8:0.2.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807025597/wn2142sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807025597/wn2142Isup2.hkl Contains datablock I

CCDC reference: 654685

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.012 Å
Disorder in main residue
R factor = 0.037
wR factor = 0.121
Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.25 Ratio
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.95
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT301_ALERT_3_C Main Residue  Disorder .........................      17.00 Perc.
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         12

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C13 H16 Br2.25 Cd1 Cl1.75 N
            Atom count from _chemical_formula_moiety:
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          6

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The preceding paper reports the structure of the tetrahedral dibromidodichloridocadmate(II), which has been isolated as the 1,2-ethanedipyridinium salt (Liu et al., 2007). The structure of propyl-1,3-di(4-pyridinium) tetrabromidocadmate(II) has been reported in the non-centrosymmetric space group Cc (Kao & Chen, 2004). The title compound, [C₁₃H₁₆N₂][CdBr₂Cl₂] is not, however, isostructural. The cadmium atom in the centrosymmetric structure is coordinated by four halogen atoms in a tetrahedral geometry; the halogen atoms are disordered (Fig. 1). The cations and anions do not have signification interactions with each other.

Related literature top

For related literature, see: Kao & Chen (2004); Liu et al. (2007).

Experimental top

The salt was synthesized from the reaction of 1,3-propanedipyridinium dibromide (0.036 g, 0.1 mmol) in methanol (5 ml) and cadmium dichloride (0.037 g, 0.2 mmol) in DMF (10 ml). The mixture was set aside for the formation of colourless crystals in 30% yield after several days.

Structure description top

For related literature, see: Kao & Chen (2004); Liu et al. (2007).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top

Fig. 1. The structure of [C₁₃H₁₆N₂][CdBr₂Cl₂], with displacement ellipsoids drawn at the 50% probability level. The bromine and chlorine atoms are disordered; the figure depicts the anion as a [CdX₄]^2- species. Hydrogen atoms are drawn as spheres of arbitrary radius.

Propane-1,3-diyldipyridinium dibromidodichloridocadmate(II) top

Crystal data top

(C₁₃H₁₆N₂)[CdBr₂Cl₂]	F(000) = 1058
M_r = 554.51	D_x = 2.003 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2441 reflections
a = 8.1159 (6) Å	θ = 2.7–21.3°
b = 15.058 (1) Å	µ = 6.32 mm⁻¹
c = 15.103 (1) Å	T = 295 K
β = 95.023 (1)°	Block, colourless
V = 1838.6 (2) Å³	0.15 × 0.10 × 0.08 mm
Z = 4

Data collection top

Bruker APEX area-detector diffractometer	3220 independent reflections
Radiation source: fine-focus sealed tube	2287 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
φ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.409, T_max = 0.632	k = −17→17
10838 measured reflections	l = −17→17

Refinement top

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0638P)²] where P = (F_o² + 2F_c²)/3
3220 reflections	(Δ/σ)_max = 0.001
201 parameters	Δρ_max = 0.82 e Å⁻³
6 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

(C₁₃H₁₆N₂)[CdBr₂Cl₂]	V = 1838.6 (2) Å³
M_r = 554.51	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.1159 (6) Å	µ = 6.32 mm⁻¹
b = 15.058 (1) Å	T = 295 K
c = 15.103 (1) Å	0.15 × 0.10 × 0.08 mm
β = 95.023 (1)°

Data collection top

Bruker APEX area-detector diffractometer	3220 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2287 reflections with I > 2σ(I)
T_min = 0.409, T_max = 0.632	R_int = 0.034
10838 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	6 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.08	Δρ_max = 0.82 e Å⁻³
3220 reflections	Δρ_min = −0.63 e Å⁻³
201 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cd1	0.25358 (6)	0.20461 (3)	0.28984 (3)	0.0586 (2)
Br1	0.4650 (9)	0.3290 (3)	0.2721 (6)	0.0757 (10)	0.4863 (18)
Cl1	0.485 (2)	0.3078 (9)	0.2754 (14)	0.0757 (10)	0.5137 (18)
Br2	0.3988 (7)	0.0714 (3)	0.3716 (4)	0.0712 (8)	0.561 (2)
Cl2	0.416 (2)	0.0906 (10)	0.3671 (15)	0.0712 (8)	0.439 (2)
Br3	0.1618 (15)	0.1511 (12)	0.1337 (11)	0.0651 (15)	0.431 (2)
Cl3	0.135 (3)	0.145 (2)	0.139 (2)	0.0651 (15)	0.569 (2)
Br4	0.0147 (3)	0.27032 (12)	0.36647 (16)	0.0712 (5)	0.771 (2)
Cl4	−0.011 (3)	0.2488 (14)	0.3558 (16)	0.0712 (5)	0.229 (2)
N1	0.6152 (5)	0.1612 (3)	0.0464 (3)	0.0528 (12)
C1	0.6960 (9)	0.1278 (5)	−0.0181 (5)	0.0695 (18)
H1	0.7119	0.1625	−0.0676	0.083*
C2	0.7553 (10)	0.0450 (6)	−0.0135 (6)	0.095 (3)
H2	0.8148	0.0240	−0.0590	0.114*
C3	0.7317 (11)	−0.0074 (6)	0.0538 (8)	0.098 (3)
H3	0.7691	−0.0658	0.0551	0.118*
C4	0.6496 (10)	0.0269 (6)	0.1227 (7)	0.096 (3)
H4	0.6339	−0.0077	0.1723	0.115*
C5	0.5921 (8)	0.1118 (5)	0.1169 (5)	0.073 (2)
H5	0.5362	0.1354	0.1628	0.088*
N2	0.9403 (6)	0.3797 (3)	0.1317 (3)	0.0568 (13)
C6	1.0594 (8)	0.3774 (5)	0.0759 (4)	0.0649 (17)
H6	1.0619	0.3315	0.0347	0.078*
C7	1.1779 (9)	0.4426 (6)	0.0793 (6)	0.084 (2)
H7	1.2612	0.4416	0.0409	0.101*
C8	1.1712 (9)	0.5093 (6)	0.1404 (6)	0.087 (2)
H8	1.2503	0.5541	0.1435	0.104*
C9	1.0487 (11)	0.5103 (6)	0.1970 (5)	0.087 (2)
H9	1.0438	0.5555	0.2386	0.105*
C10	0.9341 (9)	0.4443 (5)	0.1915 (5)	0.0731 (19)
H10	0.8505	0.4443	0.2299	0.088*
C11	0.5538 (8)	0.2530 (4)	0.0405 (5)	0.0660 (18)
H11A	0.4859	0.2640	0.0891	0.079*
H11B	0.4847	0.2604	−0.0147	0.079*
C12	0.6934 (8)	0.3208 (4)	0.0443 (5)	0.0657 (18)
H12A	0.7527	0.3149	−0.0084	0.079*
H12B	0.6470	0.3801	0.0446	0.079*
C13	0.8126 (8)	0.3086 (5)	0.1259 (5)	0.073 (2)
H13A	0.7524	0.3100	0.1786	0.087*
H13B	0.8660	0.2511	0.1235	0.087*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.0570 (3)	0.0650 (3)	0.0539 (3)	0.0085 (2)	0.0050 (2)	−0.0107 (2)
Br1	0.077 (2)	0.062 (3)	0.0900 (11)	−0.0072 (19)	0.0218 (13)	−0.022 (2)
Cl1	0.077 (2)	0.062 (3)	0.0900 (11)	−0.0072 (19)	0.0218 (13)	−0.022 (2)
Br2	0.0635 (15)	0.056 (2)	0.0904 (11)	0.0047 (14)	−0.0153 (10)	0.0029 (17)
Cl2	0.0635 (15)	0.056 (2)	0.0904 (11)	0.0047 (14)	−0.0153 (10)	0.0029 (17)
Br3	0.067 (4)	0.072 (3)	0.056 (2)	0.003 (3)	0.004 (2)	−0.0156 (17)
Cl3	0.067 (4)	0.072 (3)	0.056 (2)	0.003 (3)	0.004 (2)	−0.0156 (17)
Br4	0.0762 (11)	0.0748 (13)	0.0660 (9)	0.0202 (8)	0.0252 (7)	0.0008 (8)
Cl4	0.0762 (11)	0.0748 (13)	0.0660 (9)	0.0202 (8)	0.0252 (7)	0.0008 (8)
N1	0.051 (3)	0.056 (3)	0.051 (3)	−0.005 (2)	0.001 (2)	0.006 (2)
C1	0.085 (5)	0.064 (5)	0.062 (4)	−0.008 (4)	0.018 (4)	−0.010 (4)
C2	0.099 (7)	0.077 (6)	0.111 (7)	−0.005 (5)	0.025 (5)	−0.025 (5)
C3	0.083 (6)	0.056 (5)	0.150 (9)	−0.001 (4)	−0.025 (6)	−0.015 (6)
C4	0.092 (6)	0.076 (6)	0.112 (7)	−0.019 (5)	−0.028 (5)	0.043 (6)
C5	0.060 (4)	0.092 (6)	0.069 (5)	−0.013 (4)	0.012 (3)	0.009 (4)
N2	0.052 (3)	0.060 (3)	0.057 (3)	0.010 (3)	−0.001 (2)	0.005 (3)
C6	0.060 (4)	0.071 (5)	0.065 (4)	0.007 (4)	0.012 (3)	−0.006 (3)
C7	0.076 (5)	0.094 (6)	0.085 (6)	−0.001 (5)	0.020 (4)	0.009 (5)
C8	0.068 (5)	0.075 (5)	0.114 (7)	−0.008 (4)	−0.014 (5)	0.011 (5)
C9	0.090 (6)	0.075 (6)	0.091 (6)	0.017 (5)	−0.018 (5)	−0.018 (5)
C10	0.065 (4)	0.088 (5)	0.065 (4)	0.020 (4)	0.001 (3)	−0.006 (4)
C11	0.057 (4)	0.063 (4)	0.076 (5)	0.002 (3)	−0.004 (3)	0.009 (4)
C12	0.072 (4)	0.052 (4)	0.070 (4)	0.004 (3)	−0.011 (3)	0.005 (3)
C13	0.062 (4)	0.073 (5)	0.081 (5)	−0.006 (4)	−0.002 (4)	0.015 (4)

Geometric parameters (Å, º) top

Cd1—Cl2	2.404 (19)	N2—C10	1.331 (8)
Cd1—Cl1	2.46 (2)	N2—C6	1.338 (8)
Cd1—Br3	2.540 (17)	N2—C13	1.488 (8)
Cd1—Br4	2.544 (2)	C6—C7	1.373 (10)
Cd1—Cl4	2.53 (2)	C6—H6	0.9300
Cd1—Cl3	2.55 (3)	C7—C8	1.368 (11)
Cd1—Br1	2.570 (8)	C7—H7	0.9300
Cd1—Br2	2.585 (5)	C8—C9	1.366 (11)
N1—C1	1.320 (8)	C8—H8	0.9300
N1—C5	1.327 (8)	C9—C10	1.358 (10)
N1—C11	1.469 (8)	C9—H9	0.9300
C1—C2	1.336 (11)	C10—H10	0.9300
C1—H1	0.9300	C11—C12	1.522 (9)
C2—C3	1.314 (12)	C11—H11A	0.9700
C2—H2	0.9300	C11—H11B	0.9700
C3—C4	1.383 (12)	C12—C13	1.511 (9)
C3—H3	0.9300	C12—H12A	0.9700
C4—C5	1.362 (11)	C12—H12B	0.9700
C4—H4	0.9300	C13—H13A	0.9700
C5—H5	0.9300	C13—H13B	0.9700

Cl2—Cd1—Cl1	95.9 (5)	C5—C4—H4	120.4
Cl2—Cd1—Br3	109.1 (7)	C3—C4—H4	120.4
Cl1—Cd1—Br3	106.4 (6)	N1—C5—C4	120.4 (7)
Cl2—Cd1—Br4	117.7 (6)	N1—C5—H5	119.8
Cl1—Cd1—Br4	114.4 (3)	C4—C5—H5	119.8
Br3—Cd1—Br4	111.9 (3)	C10—N2—C6	121.3 (6)
Cl2—Cd1—Cl4	116.4 (8)	C10—N2—C13	119.9 (6)
Cl1—Cd1—Cl4	123.3 (6)	C6—N2—C13	118.8 (6)
Br3—Cd1—Cl4	105.0 (6)	N2—C6—C7	119.9 (7)
Br4—Cd1—Cl4	9.3 (5)	N2—C6—H6	120.0
Cl2—Cd1—Cl3	109.2 (9)	C7—C6—H6	120.0
Cl1—Cd1—Cl3	112.1 (8)	C8—C7—C6	118.8 (7)
Br3—Cd1—Cl3	5.9 (7)	C8—C7—H7	120.6
Br4—Cd1—Cl3	107.3 (6)	C6—C7—H7	120.6
Cl4—Cd1—Cl3	100.1 (7)	C7—C8—C9	120.3 (8)
Cl2—Cd1—Br1	103.2 (4)	C7—C8—H8	119.9
Cl1—Cd1—Br1	7.9 (4)	C9—C8—H8	119.9
Br3—Cd1—Br1	106.2 (4)	C10—C9—C8	119.0 (8)
Br4—Cd1—Br1	107.84 (13)	C10—C9—H9	120.5
Cl4—Cd1—Br1	116.5 (5)	C8—C9—H9	120.5
Cl3—Cd1—Br1	111.6 (6)	N2—C10—C9	120.6 (7)
Cl2—Cd1—Br2	6.4 (5)	N2—C10—H10	119.7
Cl1—Cd1—Br2	102.2 (4)	C9—C10—H10	119.7
Br3—Cd1—Br2	106.4 (4)	N1—C11—C12	112.4 (5)
Br4—Cd1—Br2	114.72 (16)	N1—C11—H11A	109.1
Cl4—Cd1—Br2	112.5 (6)	C12—C11—H11A	109.1
Cl3—Cd1—Br2	105.8 (8)	N1—C11—H11B	109.1
Br1—Cd1—Br2	109.55 (17)	C12—C11—H11B	109.1
C1—N1—C5	119.6 (6)	H11A—C11—H11B	107.9
C1—N1—C11	120.1 (5)	C13—C12—C11	111.8 (6)
C5—N1—C11	120.3 (6)	C13—C12—H12A	109.3
N1—C1—C2	121.1 (7)	C11—C12—H12A	109.3
N1—C1—H1	119.4	C13—C12—H12B	109.3
C2—C1—H1	119.4	C11—C12—H12B	109.3
C3—C2—C1	121.7 (8)	H12A—C12—H12B	107.9
C3—C2—H2	119.2	N2—C13—C12	110.7 (6)
C1—C2—H2	119.2	N2—C13—H13A	109.5
C2—C3—C4	118.0 (8)	C12—C13—H13A	109.5
C2—C3—H3	121.0	N2—C13—H13B	109.5
C4—C3—H3	121.0	C12—C13—H13B	109.5
C5—C4—C3	119.2 (8)	H13A—C13—H13B	108.1

C5—N1—C1—C2	−0.2 (10)	C6—C7—C8—C9	0.2 (12)
C11—N1—C1—C2	178.9 (7)	C7—C8—C9—C10	0.0 (12)
N1—C1—C2—C3	2.1 (13)	C6—N2—C10—C9	0.4 (10)
C1—C2—C3—C4	−3.0 (13)	C13—N2—C10—C9	−179.2 (6)
C2—C3—C4—C5	2.1 (12)	C8—C9—C10—N2	−0.3 (11)
C1—N1—C5—C4	−0.7 (9)	C1—N1—C11—C12	−66.1 (7)
C11—N1—C5—C4	−179.7 (6)	C5—N1—C11—C12	112.9 (7)
C3—C4—C5—N1	−0.3 (11)	N1—C11—C12—C13	−54.8 (8)
C10—N2—C6—C7	−0.2 (10)	C10—N2—C13—C12	106.4 (7)
C13—N2—C6—C7	179.4 (6)	C6—N2—C13—C12	−73.3 (8)
N2—C6—C7—C8	−0.1 (11)	C11—C12—C13—N2	−175.6 (5)

Experimental details

Crystal data
Chemical formula	(C₁₃H₁₆N₂)[CdBr₂Cl₂]
M_r	554.51
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	8.1159 (6), 15.058 (1), 15.103 (1)
β (°)	95.023 (1)
V (Å³)	1838.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.32
Crystal size (mm)	0.15 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEX area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.409, 0.632
No. of measured, independent and observed [I > 2σ(I)] reflections	10838, 3220, 2287
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.121, 1.08
No. of reflections	3220
No. of parameters	201
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.82, −0.63

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).

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