4-(Dimethyl­amino)­pyridinium tetra­chlorido(quinoline-2-carboxyl­ato-κ2N,O)stannate(IV)

Najafi, E.; Amini, M.M.; Ng, S.W.

doi:10.1107/S1600536811031473

4-(Dimethylamino)pyridinium tetrachlorido(quinoline-2-carboxylato-κ²N,O)stannate(IV)

In the title salt, (C₇H₁₁N₂)[SnCl₄(C₁₀H₆NO₂)], the Sn^IV atom is chelated by the N,O-bidentate carboxylate ions and four chloride ions, showing a distorted octahedral SnNOCl₄ coordination. In the crystal, the cation and anion are linked by a pyridinium–carboxylate N—H

O hydrogen bond.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811031473/xu5284sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536811031473/xu5284Isup2.hkl Contains datablock I

CCDC reference: 845227

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.021
wR factor = 0.047
Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......      0.960
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ          ?
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .         31 A   3 
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          2
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600        189

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Sn1    --  Cl1     ..        9.7 su
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

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

Comment top

We have recently synthesized some ammonium tetrachlorido(carboxylato)stannates; in a recent study, we reacted stannic chloride with pyridine-2-carboxylic acid and triethylamine to yield the chelated stannate salt (Najafi et al., 2011). The use of quinoline-2-carboxylic acid and 4-dimethyaminopyridine yielded the expected dimethylaminopyridinium stannate in which the amine is protonated on the aromatic nitrogen atom (Scheme I, Fig. 1). The Sn^IV atom is chelated by the N,O-bidentate carboxylate ligand and four chloride ions, and shows octahedral SnNOCl₄ coordination at the metal atom. The cation and anion are linked an N–H_pyridinium···O hydrogen bond (Table 1).

Related literature top

For a related ammonium tetrachlorido(pyridine-2-carboxylato)stannate(IV), see: Najafi et al. (2011).

Experimental top

Stannic chloride pentahydrate (1 mmol), quinoline-2-carboxylic acid (1 mmol) and 4-dimethylaminopyridine (1 mmol) were loaded into a convection tube and the tube was filled with dry methanol and kept at 333 K. Colorless crystals were collected from the side arm after several days.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of (C₇H₁₁N₂)[SnCl₄(C₁₀H₆NO₂)] at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

4-(Dimethylamino)pyridinium tetrachlorido(quinoline-2-carboxylato-κ²N,O)stannate(IV) top

Crystal data top

(C₇H₁₁N₂)[SnCl₄(C₁₀H₆NO₂)]	Z = 2
M_r = 555.83	F(000) = 548
Triclinic, P1	D_x = 1.771 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6681 (3) Å	Cell parameters from 5833 reflections
b = 8.8407 (4) Å	θ = 2.4–29.2°
c = 14.4447 (5) Å	µ = 1.76 mm⁻¹
α = 96.721 (3)°	T = 100 K
β = 91.924 (3)°	Block, colorless
γ = 108.038 (4)°	0.30 × 0.20 × 0.10 mm
V = 1042.43 (7) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4610 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4202 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.022
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.5°
ω scans	h = −8→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→11
T_min = 0.621, T_max = 0.844	l = −18→18
8056 measured reflections

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.047	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0181P)² + 0.127P] where P = (F_o² + 2F_c²)/3
4610 reflections	(Δ/σ)_max = 0.001
250 parameters	Δρ_max = 0.52 e Å⁻³
1 restraint	Δρ_min = −0.49 e Å⁻³

Crystal data top

(C₇H₁₁N₂)[SnCl₄(C₁₀H₆NO₂)]	γ = 108.038 (4)°
M_r = 555.83	V = 1042.43 (7) Å³
Triclinic, P1	Z = 2
a = 8.6681 (3) Å	Mo Kα radiation
b = 8.8407 (4) Å	µ = 1.76 mm⁻¹
c = 14.4447 (5) Å	T = 100 K
α = 96.721 (3)°	0.30 × 0.20 × 0.10 mm
β = 91.924 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4610 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	4202 reflections with I > 2σ(I)
T_min = 0.621, T_max = 0.844	R_int = 0.022
8056 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	1 restraint
wR(F²) = 0.047	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.52 e Å⁻³
4610 reflections	Δρ_min = −0.49 e Å⁻³
250 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.361135 (16)	0.258730 (15)	0.271428 (9)	0.01232 (5)
Cl1	0.16903 (6)	0.37830 (6)	0.33361 (4)	0.02211 (12)
Cl2	0.13953 (6)	0.04597 (6)	0.18599 (3)	0.01824 (11)
Cl3	0.41373 (6)	0.41174 (6)	0.14341 (4)	0.02133 (11)
Cl4	0.58090 (6)	0.44245 (6)	0.37084 (4)	0.02246 (12)
O1	0.51697 (17)	0.14313 (16)	0.21142 (9)	0.0165 (3)
O2	0.57573 (18)	−0.08559 (17)	0.19327 (10)	0.0207 (3)
N1	0.36250 (19)	0.06808 (18)	0.36458 (10)	0.0124 (3)
N2	1.0685 (2)	0.3405 (2)	−0.12106 (11)	0.0173 (4)
N3	0.7058 (2)	0.2281 (2)	0.05939 (12)	0.0203 (4)
H3	0.629 (2)	0.206 (3)	0.0979 (13)	0.024 (6)*
C1	0.2921 (2)	0.0400 (2)	0.44784 (13)	0.0134 (4)
C2	0.2404 (2)	0.1582 (2)	0.49972 (13)	0.0173 (4)
H2	0.2535	0.2582	0.4777	0.021*
C3	0.1712 (3)	0.1279 (3)	0.58221 (14)	0.0203 (5)
H3A	0.1369	0.2080	0.6172	0.024*
C4	0.1499 (3)	−0.0194 (3)	0.61614 (14)	0.0219 (5)
H4	0.0987	−0.0389	0.6726	0.026*
C5	0.2022 (2)	−0.1341 (3)	0.56843 (14)	0.0194 (5)
H5	0.1888	−0.2327	0.5923	0.023*
C6	0.2768 (2)	−0.1071 (2)	0.48305 (13)	0.0158 (4)
C7	0.3379 (2)	−0.2201 (2)	0.43302 (14)	0.0172 (4)
H7	0.3269	−0.3199	0.4550	0.021*
C8	0.4130 (2)	−0.1860 (2)	0.35297 (13)	0.0164 (4)
H8	0.4577	−0.2598	0.3196	0.020*
C9	0.4230 (2)	−0.0400 (2)	0.32101 (13)	0.0133 (4)
C10	0.5114 (2)	0.0037 (2)	0.23433 (13)	0.0145 (4)
C11	0.9504 (2)	0.3054 (2)	−0.06169 (13)	0.0143 (4)
C12	0.9714 (3)	0.2416 (2)	0.02178 (14)	0.0184 (4)
H12	1.0717	0.2248	0.0375	0.022*
C13	0.8486 (3)	0.2047 (2)	0.07897 (14)	0.0205 (5)
H13	0.8638	0.1612	0.1344	0.025*
C14	0.6811 (3)	0.2898 (2)	−0.01880 (14)	0.0199 (5)
H14	0.5797	0.3062	−0.0316	0.024*
C15	0.7983 (2)	0.3288 (2)	−0.07943 (14)	0.0166 (4)
H15	0.7784	0.3720	−0.1341	0.020*
C16	1.2127 (3)	0.2906 (3)	−0.10898 (16)	0.0242 (5)
H16A	1.2761	0.3488	−0.0511	0.036*
H16B	1.2794	0.3146	−0.1621	0.036*
H16C	1.1793	0.1750	−0.1057	0.036*
C17	1.0413 (3)	0.3978 (3)	−0.20898 (14)	0.0258 (5)
H17A	0.9928	0.4840	−0.1971	0.039*
H17B	0.9676	0.3091	−0.2522	0.039*
H17C	1.1454	0.4388	−0.2367	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01240 (7)	0.01035 (8)	0.01461 (8)	0.00357 (6)	0.00258 (5)	0.00280 (5)
Cl1	0.0238 (3)	0.0179 (3)	0.0275 (3)	0.0104 (2)	0.0071 (2)	0.0023 (2)
Cl2	0.0183 (3)	0.0146 (2)	0.0197 (2)	0.0034 (2)	−0.0038 (2)	0.00033 (19)
Cl3	0.0229 (3)	0.0214 (3)	0.0235 (3)	0.0086 (2)	0.0061 (2)	0.0125 (2)
Cl4	0.0208 (3)	0.0168 (3)	0.0243 (3)	−0.0010 (2)	−0.0032 (2)	0.0012 (2)
O1	0.0185 (7)	0.0168 (7)	0.0173 (7)	0.0084 (6)	0.0074 (6)	0.0045 (6)
O2	0.0244 (8)	0.0229 (8)	0.0197 (8)	0.0145 (7)	0.0054 (6)	0.0025 (6)
N1	0.0110 (8)	0.0117 (8)	0.0134 (8)	0.0021 (7)	0.0000 (7)	0.0015 (6)
N2	0.0155 (9)	0.0163 (9)	0.0181 (9)	0.0026 (7)	0.0042 (7)	0.0005 (7)
N3	0.0200 (10)	0.0245 (10)	0.0175 (9)	0.0072 (8)	0.0089 (8)	0.0042 (7)
C1	0.0110 (9)	0.0149 (10)	0.0122 (9)	0.0010 (8)	−0.0007 (8)	0.0027 (8)
C2	0.0167 (10)	0.0170 (11)	0.0171 (10)	0.0039 (9)	−0.0004 (8)	0.0024 (8)
C3	0.0164 (11)	0.0256 (12)	0.0177 (10)	0.0062 (9)	0.0013 (9)	−0.0013 (9)
C4	0.0159 (11)	0.0329 (13)	0.0134 (10)	0.0027 (10)	0.0022 (8)	0.0030 (9)
C5	0.0159 (10)	0.0194 (11)	0.0183 (10)	−0.0027 (9)	−0.0010 (9)	0.0075 (9)
C6	0.0126 (10)	0.0164 (10)	0.0155 (10)	0.0006 (8)	−0.0029 (8)	0.0032 (8)
C7	0.0187 (11)	0.0117 (10)	0.0187 (10)	0.0012 (9)	−0.0048 (9)	0.0034 (8)
C8	0.0166 (10)	0.0146 (10)	0.0169 (10)	0.0052 (9)	−0.0034 (8)	−0.0013 (8)
C9	0.0113 (9)	0.0139 (10)	0.0136 (10)	0.0033 (8)	−0.0012 (8)	0.0003 (8)
C10	0.0120 (10)	0.0171 (10)	0.0136 (10)	0.0039 (8)	−0.0016 (8)	0.0019 (8)
C11	0.0157 (10)	0.0098 (9)	0.0154 (10)	0.0021 (8)	0.0023 (8)	−0.0022 (7)
C12	0.0170 (10)	0.0204 (11)	0.0193 (10)	0.0084 (9)	0.0006 (9)	0.0020 (8)
C13	0.0245 (12)	0.0204 (11)	0.0179 (10)	0.0077 (10)	0.0017 (9)	0.0062 (8)
C14	0.0178 (11)	0.0230 (12)	0.0198 (11)	0.0096 (9)	0.0000 (9)	−0.0020 (9)
C15	0.0195 (11)	0.0174 (10)	0.0143 (10)	0.0086 (9)	−0.0002 (8)	0.0002 (8)
C16	0.0132 (10)	0.0261 (12)	0.0317 (12)	0.0054 (9)	0.0070 (9)	−0.0015 (10)
C17	0.0333 (13)	0.0236 (12)	0.0204 (11)	0.0065 (10)	0.0118 (10)	0.0068 (9)

Geometric parameters (Å, º) top

Sn1—O1	2.0848 (13)	C4—H4	0.9500
Sn1—N1	2.2790 (16)	C5—C6	1.422 (3)
Sn1—Cl1	2.3802 (5)	C5—H5	0.9500
Sn1—Cl4	2.3840 (5)	C6—C7	1.409 (3)
Sn1—Cl3	2.3912 (5)	C7—C8	1.365 (3)
Sn1—Cl2	2.4106 (5)	C7—H7	0.9500
O1—C10	1.301 (2)	C8—C9	1.400 (3)
O2—C10	1.213 (2)	C8—H8	0.9500
N1—C9	1.333 (2)	C9—C10	1.516 (3)
N1—C1	1.381 (2)	C11—C15	1.416 (3)
N2—C11	1.343 (2)	C11—C12	1.419 (3)
N2—C17	1.459 (3)	C12—C13	1.353 (3)
N2—C16	1.460 (3)	C12—H12	0.9500
N3—C13	1.343 (3)	C13—H13	0.9500
N3—C14	1.348 (3)	C14—C15	1.353 (3)
N3—H3	0.869 (9)	C14—H14	0.9500
C1—C2	1.408 (3)	C15—H15	0.9500
C1—C6	1.421 (3)	C16—H16A	0.9800
C2—C3	1.369 (3)	C16—H16B	0.9800
C2—H2	0.9500	C16—H16C	0.9800
C3—C4	1.406 (3)	C17—H17A	0.9800
C3—H3A	0.9500	C17—H17B	0.9800
C4—C5	1.360 (3)	C17—H17C	0.9800

O1—Sn1—N1	75.24 (5)	C7—C6—C5	122.27 (19)
O1—Sn1—Cl1	176.27 (4)	C1—C6—C5	118.72 (19)
N1—Sn1—Cl1	104.74 (4)	C8—C7—C6	119.87 (18)
O1—Sn1—Cl4	90.93 (4)	C8—C7—H7	120.1
N1—Sn1—Cl4	88.46 (4)	C6—C7—H7	120.1
Cl1—Sn1—Cl4	92.797 (19)	C7—C8—C9	118.64 (19)
O1—Sn1—Cl3	85.08 (4)	C7—C8—H8	120.7
N1—Sn1—Cl3	160.21 (4)	C9—C8—H8	120.7
Cl1—Sn1—Cl3	94.762 (18)	N1—C9—C8	123.44 (17)
Cl4—Sn1—Cl3	93.991 (19)	N1—C9—C10	116.83 (17)
O1—Sn1—Cl2	87.29 (4)	C8—C9—C10	119.70 (17)
N1—Sn1—Cl2	83.40 (4)	O2—C10—O1	124.30 (18)
Cl1—Sn1—Cl2	89.002 (18)	O2—C10—C9	120.59 (18)
Cl4—Sn1—Cl2	171.852 (17)	O1—C10—C9	115.05 (17)
Cl3—Sn1—Cl2	93.779 (18)	N2—C11—C15	121.88 (18)
C10—O1—Sn1	118.81 (12)	N2—C11—C12	121.52 (19)
C9—N1—C1	119.22 (16)	C15—C11—C12	116.60 (18)
C9—N1—Sn1	110.22 (12)	C13—C12—C11	119.88 (19)
C1—N1—Sn1	129.82 (13)	C13—C12—H12	120.1
C11—N2—C17	120.69 (18)	C11—C12—H12	120.1
C11—N2—C16	120.42 (17)	N3—C13—C12	121.67 (19)
C17—N2—C16	117.65 (17)	N3—C13—H13	119.2
C13—N3—C14	120.35 (18)	C12—C13—H13	119.2
C13—N3—H3	120.3 (15)	N3—C14—C15	121.2 (2)
C14—N3—H3	119.4 (15)	N3—C14—H14	119.4
N1—C1—C2	120.50 (17)	C15—C14—H14	119.4
N1—C1—C6	119.72 (17)	C14—C15—C11	120.29 (19)
C2—C1—C6	119.74 (17)	C14—C15—H15	119.9
C3—C2—C1	119.50 (19)	C11—C15—H15	119.9
C3—C2—H2	120.2	N2—C16—H16A	109.5
C1—C2—H2	120.2	N2—C16—H16B	109.5
C2—C3—C4	121.3 (2)	H16A—C16—H16B	109.5
C2—C3—H3A	119.3	N2—C16—H16C	109.5
C4—C3—H3A	119.3	H16A—C16—H16C	109.5
C5—C4—C3	120.29 (19)	H16B—C16—H16C	109.5
C5—C4—H4	119.9	N2—C17—H17A	109.5
C3—C4—H4	119.9	N2—C17—H17B	109.5
C4—C5—C6	120.34 (19)	H17A—C17—H17B	109.5
C4—C5—H5	119.8	N2—C17—H17C	109.5
C6—C5—H5	119.8	H17A—C17—H17C	109.5
C7—C6—C1	119.00 (17)	H17B—C17—H17C	109.5

N1—Sn1—O1—C10	17.16 (14)	C4—C5—C6—C1	−1.4 (3)
Cl4—Sn1—O1—C10	105.32 (14)	C1—C6—C7—C8	1.2 (3)
Cl3—Sn1—O1—C10	−160.75 (14)	C5—C6—C7—C8	−177.90 (19)
Cl2—Sn1—O1—C10	−66.72 (14)	C6—C7—C8—C9	−1.9 (3)
O1—Sn1—N1—C9	−16.03 (12)	C1—N1—C9—C8	2.9 (3)
Cl1—Sn1—N1—C9	160.11 (12)	Sn1—N1—C9—C8	−168.24 (16)
Cl4—Sn1—N1—C9	−107.40 (12)	C1—N1—C9—C10	−174.97 (16)
Cl3—Sn1—N1—C9	−9.9 (2)	Sn1—N1—C9—C10	13.9 (2)
Cl2—Sn1—N1—C9	72.90 (12)	C7—C8—C9—N1	−0.2 (3)
O1—Sn1—N1—C1	174.03 (17)	C7—C8—C9—C10	177.68 (17)
Cl1—Sn1—N1—C1	−9.83 (16)	Sn1—O1—C10—O2	167.37 (15)
Cl4—Sn1—N1—C1	82.65 (16)	Sn1—O1—C10—C9	−15.3 (2)
Cl3—Sn1—N1—C1	−179.84 (11)	N1—C9—C10—O2	176.83 (18)
Cl2—Sn1—N1—C1	−97.05 (16)	C8—C9—C10—O2	−1.1 (3)
C9—N1—C1—C2	174.22 (18)	N1—C9—C10—O1	−0.6 (3)
Sn1—N1—C1—C2	−16.6 (3)	C8—C9—C10—O1	−178.61 (17)
C9—N1—C1—C6	−3.6 (3)	C17—N2—C11—C15	−2.8 (3)
Sn1—N1—C1—C6	165.62 (14)	C16—N2—C11—C15	−169.76 (18)
N1—C1—C2—C3	−179.86 (18)	C17—N2—C11—C12	176.65 (18)
C6—C1—C2—C3	−2.1 (3)	C16—N2—C11—C12	9.6 (3)
C1—C2—C3—C4	−0.3 (3)	N2—C11—C12—C13	−178.67 (19)
C2—C3—C4—C5	1.8 (3)	C15—C11—C12—C13	0.8 (3)
C3—C4—C5—C6	−0.9 (3)	C14—N3—C13—C12	0.0 (3)
N1—C1—C6—C7	1.6 (3)	C11—C12—C13—N3	−0.5 (3)
C2—C1—C6—C7	−176.23 (18)	C13—N3—C14—C15	0.3 (3)
N1—C1—C6—C5	−179.32 (17)	N3—C14—C15—C11	−0.1 (3)
C2—C1—C6—C5	2.9 (3)	N2—C11—C15—C14	178.95 (19)
C4—C5—C6—C7	177.70 (19)	C12—C11—C15—C14	−0.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.87 (1)	1.98 (1)	2.816 (2)	160 (2)

Experimental details

Crystal data
Chemical formula	(C₇H₁₁N₂)[SnCl₄(C₁₀H₆NO₂)]
M_r	555.83
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.6681 (3), 8.8407 (4), 14.4447 (5)
α, β, γ (°)	96.721 (3), 91.924 (3), 108.038 (4)
V (Å³)	1042.43 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.76
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.621, 0.844
No. of measured, independent and observed [I > 2σ(I)] reflections	8056, 4610, 4202
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.047, 1.06
No. of reflections	4610
No. of parameters	250
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.49

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).