Rhodamine 6G hexa­chlorido­stannate(IV) acetonitrile disolvate

Venkatraman, R.; Sitole, L.; Fronczek, F.R.

doi:10.1107/S1600536807066287

Rhodamine 6G hexachloridostannate(IV) acetonitrile disolvate

R. Venkatraman, L. Sitole and F. R. Fronczek

In the title compound, bis({6-ethylamino-10-[2-(methoxycarbonyl)phenyl]-2,7-dimethylxanthen-3-ylidene}ethanaminium) hexachloridotin(IV) acetonitrile disolvate, (C₂₇H₂₉N₂O₃)₂[SnCl₆]·2C₂H₃N, the octahedral SnCl₆²⁻ anion lies on an inversion center. The xanthene ring system is essentially planar, with an average deviation of 0.020 Å, and the substituent benzene ring forms a dihedral angle of 85.89 (2)° with it. The Sn—Cl distances are in the range 2.4237 (3)–2.4454 (3) Å. There are N—H

Cl hydrogen bonds between SnCl₆²⁻ ions and rhodamine 6G cations as well as π–π stacking interactions between rhodamine 6G cations (interplanar distance of 3.827 Å).

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807066287/pv2056sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807066287/pv2056Isup2.hkl Contains datablock I

CCDC reference: 674356

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Key indicators

Single-crystal X-ray study
T = 90 K
Mean (C-C) = 0.002 Å
R factor = 0.029
wR factor = 0.073
Data-to-parameter ratio = 39.8

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Comment top

The excellent photo-physical properties of rhodamines are well known (Herz, 1974; Johnson & McGrane, 1993; Nguyen & Meyer, 1992), and recently metal complexes of rhodamine 6 G have been reported by several authors (Bhagavthy et al., 1993; Fun et al., 1997; Wang et al., 1997; Liu et al., 1998). The aggregative properties of cationic species of the dye were observed to be dependent on the anionic environment created by the metal ions. We have synthesized a rhodamine 6 G derivative, 9-[2-methoxycarbonyl)phenyl]-3,6-bis(ethylamino)-2,7-dimethylxanthylium hexachlorotin(IV) diacetonitrile solvate, (I), the structure of which is presented in this paper.

The structure of (I) consists of discrete SnCl₆^2- anions lying on inversion centers, rhodamine 6 G cations and acetonitrile solvent molecules (Fig. 1). The xanthene ring of the cation is planar within an average deviation of 0.020 Å (maximum deviation is 0.045 (1) Å for C4), and the phenyl ring forms a dihedral angle of 85.89 (2)° with it. The C—N distances N1—C24 and N2—C26 are normal for this type of single bond, whereas C3—N1 and C11—N2 are much shorter, showing partial double-bond character; details are in the Table. A similar trend is observed in the other rhodamine 6 G cations (Wang et al., 1997; Liu et al., 1998).

Both hydrogen bonding between cations and anions and π-π stacking interactions between rhodamine 6 G cations exist. Parallel rhodamine ions related by the inversion center have an interplanar distance of 3.827 Å (Fig. 2), and are slipped such that their O1—C13 bonds exactly overlap.

Related literature top

For related literature, see: Bhagavthy et al. (1993); Fun et al. (1997); Herz (1974); Johnson & McGrane (1993); Liu et al. (1998); Nguyen & Meyer (1992); Wang et al. (1997). For the structure of the analogous ethyl ester as the chloride salt hydrate, see: Adhikesavalu et al. (2001).

Experimental top

Diphenyl tin dichloride (0.344 g, 1 mmol) was dissolved in 20 ml me thanol, and then 20 ml of methanol solution of rhodamine 6 G (0.479 g, 1 mmol) was added. The bright red solution was refluxed for 1 hr, whereafter red brown solid were obtained on cooling. Suitable size crystals were obtained by the recrystallization at room temperature from acetonitrile (yield ca 85%).

Structure description top

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. Numbering scheme and ellipsoids at the 50% level. (i = 1 - x, -y, -z).
	Fig. 2. The unit cell, showing stacking of rhodamine cations and hydrogen bonding.

bis({6-ethylamino-10-[2-(methoxycarbonyl)phenyl]-2,7-dimethylxanthen-3- ylidene}ethanaminium) hexachloridotin(IV) acetonitrile disolvate top

Crystal data top

(C₂₇H₂₉N₂O₃)₂[SnCl₆]·2C₂H₃N	Z = 1
M_r = 1272.54	F(000) = 654
Triclinic, P1	D_x = 1.440 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7871 (10) Å	Cell parameters from 13141 reflections
b = 11.7827 (11) Å	θ = 2.5–36.8°
c = 13.2893 (12) Å	µ = 0.76 mm⁻¹
α = 80.583 (4)°	T = 90 K
β = 77.309 (4)°	Fragment, red-orange
γ = 82.467 (4)°	0.28 × 0.27 × 0.25 mm
V = 1467.7 (2) Å³

Data collection top

Nonius KappaCCD diffractometer with Oxford Cryostream	14412 independent reflections
Radiation source: fine-focus sealed tube	12969 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω scans with κ offsets	θ_max = 36.8°, θ_min = 2.7°
Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997)	h = −16→16
T_min = 0.815, T_max = 0.832	k = −19→19
54250 measured reflections	l = −22→21

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)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.073	w = 1/[σ²(F_o²) + (0.0303P)² + 0.821P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
14412 reflections	Δρ_max = 0.74 e Å⁻³
362 parameters	Δρ_min = −1.24 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0053 (5)

Crystal data top

(C₂₇H₂₉N₂O₃)₂[SnCl₆]·2C₂H₃N	γ = 82.467 (4)°
M_r = 1272.54	V = 1467.7 (2) Å³
Triclinic, P1	Z = 1
a = 9.7871 (10) Å	Mo Kα radiation
b = 11.7827 (11) Å	µ = 0.76 mm⁻¹
c = 13.2893 (12) Å	T = 90 K
α = 80.583 (4)°	0.28 × 0.27 × 0.25 mm
β = 77.309 (4)°

Data collection top

Nonius KappaCCD diffractometer with Oxford Cryostream	14412 independent reflections
Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997)	12969 reflections with I > 2σ(I)
T_min = 0.815, T_max = 0.832	R_int = 0.024
54250 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.74 e Å⁻³
14412 reflections	Δρ_min = −1.24 e Å⁻³
362 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
Sn1	0.5000	0.0000	0.0000	0.00926 (3)
Cl1	0.53900 (3)	0.04133 (2)	0.164917 (19)	0.01502 (5)
Cl2	0.51522 (3)	0.20275 (2)	−0.07554 (2)	0.01362 (4)
Cl3	0.24802 (3)	0.04038 (2)	0.05732 (2)	0.01381 (4)
O1	0.40633 (8)	0.58975 (7)	0.38427 (6)	0.01354 (13)
O2	1.06811 (9)	0.46854 (8)	0.36352 (7)	0.01853 (15)
O3	0.83375 (10)	0.47563 (9)	0.39044 (9)	0.0272 (2)
N1	0.42673 (10)	0.33594 (9)	0.13842 (8)	0.01642 (17)
H1N	0.4731 (19)	0.3059 (16)	0.0897 (14)	0.020*
N2	0.35159 (10)	0.83221 (9)	0.64389 (7)	0.01542 (16)
H2N	0.3892 (19)	0.8743 (16)	0.6750 (14)	0.019*
C1	0.48174 (10)	0.54161 (9)	0.30004 (8)	0.01118 (15)
C2	0.41464 (10)	0.46614 (9)	0.26289 (8)	0.01275 (16)
H2	0.3206	0.4516	0.2948	0.015*
C3	0.48671 (11)	0.41085 (9)	0.17721 (8)	0.01291 (16)
C4	0.63032 (11)	0.43418 (9)	0.12992 (8)	0.01360 (16)
C5	0.69115 (11)	0.51151 (9)	0.16815 (8)	0.01310 (16)
H5	0.7846	0.5275	0.1359	0.016*
C6	0.62049 (10)	0.56913 (9)	0.25423 (8)	0.01122 (15)
C7	0.68061 (10)	0.64746 (8)	0.29612 (8)	0.01058 (15)
C8	0.60111 (10)	0.69685 (9)	0.38325 (8)	0.01108 (15)
C9	0.65144 (10)	0.77664 (9)	0.43315 (8)	0.01170 (15)
H9	0.7429	0.8005	0.4054	0.014*
C10	0.57244 (11)	0.82019 (9)	0.51976 (8)	0.01222 (15)
C11	0.43234 (11)	0.78594 (9)	0.56098 (8)	0.01258 (16)
C12	0.38037 (11)	0.70714 (9)	0.51364 (8)	0.01331 (16)
H12	0.2889	0.6832	0.5408	0.016*
C13	0.46414 (10)	0.66475 (9)	0.42693 (8)	0.01159 (15)
C14	0.70941 (13)	0.37222 (11)	0.04109 (10)	0.0197 (2)
H14A	0.8074	0.3907	0.0232	0.030*
H14B	0.6655	0.3969	−0.0195	0.030*
H14C	0.7069	0.2886	0.0616	0.030*
C15	0.62856 (12)	0.90417 (10)	0.57043 (9)	0.01553 (17)
H15A	0.7239	0.9186	0.5326	0.023*
H15B	0.6310	0.8716	0.6428	0.023*
H15C	0.5674	0.9770	0.5689	0.023*
C16	0.82316 (10)	0.68456 (8)	0.24669 (8)	0.01064 (15)
C17	0.94862 (10)	0.62467 (9)	0.27097 (8)	0.01147 (15)
C18	1.07793 (11)	0.66730 (9)	0.22341 (8)	0.01360 (16)
H18	1.1625	0.6273	0.2402	0.016*
C19	1.08333 (11)	0.76787 (9)	0.15174 (8)	0.01417 (17)
H19	1.1713	0.7963	0.1196	0.017*
C20	0.95942 (12)	0.82636 (10)	0.12744 (9)	0.01498 (17)
H20	0.9629	0.8948	0.0784	0.018*
C21	0.82987 (11)	0.78526 (9)	0.17463 (8)	0.01412 (17)
H21	0.7457	0.8260	0.1576	0.017*
C22	0.94161 (11)	0.51676 (9)	0.34679 (9)	0.01400 (17)
C23	1.06484 (13)	0.36159 (11)	0.43498 (10)	0.0211 (2)
H23A	0.9925	0.3717	0.4976	0.032*
H23B	1.1569	0.3406	0.4543	0.032*
H23C	1.0429	0.3000	0.4014	0.032*
C24	0.28833 (12)	0.29543 (10)	0.18084 (9)	0.01633 (18)
H24A	0.2628	0.3019	0.2562	0.020*
H24B	0.2931	0.2127	0.1733	0.020*
C25	0.17375 (14)	0.36257 (13)	0.12788 (12)	0.0258 (2)
H25A	0.1665	0.4443	0.1367	0.039*
H25B	0.0836	0.3314	0.1593	0.039*
H25C	0.1973	0.3554	0.0535	0.039*
C26	0.20472 (12)	0.81093 (11)	0.68565 (9)	0.0185 (2)
H26A	0.2000	0.7296	0.7190	0.022*
H26B	0.1527	0.8234	0.6281	0.022*
C27	0.13662 (13)	0.89136 (12)	0.76511 (10)	0.0232 (2)
H27A	0.1871	0.8779	0.8227	0.035*
H27B	0.0382	0.8763	0.7920	0.035*
H27C	0.1406	0.9718	0.7319	0.035*
N3	−0.01218 (17)	0.87440 (15)	0.42927 (13)	0.0429 (4)
C28	0.09893 (16)	0.88240 (12)	0.37996 (11)	0.0259 (2)
C29	0.23901 (15)	0.89178 (14)	0.31671 (11)	0.0267 (3)
H29A	0.2723	0.8203	0.2862	0.040*
H29B	0.3031	0.9042	0.3603	0.040*
H29C	0.2364	0.9571	0.2609	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01002 (4)	0.00916 (4)	0.00947 (4)	−0.00130 (3)	−0.00229 (3)	−0.00309 (3)
Cl1	0.01755 (10)	0.01736 (11)	0.01246 (10)	−0.00091 (8)	−0.00530 (8)	−0.00629 (8)
Cl2	0.01605 (10)	0.01023 (9)	0.01489 (10)	−0.00222 (7)	−0.00319 (8)	−0.00189 (7)
Cl3	0.01070 (9)	0.01542 (10)	0.01489 (10)	−0.00084 (7)	−0.00195 (7)	−0.00214 (8)
O1	0.0112 (3)	0.0151 (3)	0.0155 (3)	−0.0041 (2)	0.0009 (2)	−0.0078 (3)
O2	0.0122 (3)	0.0194 (4)	0.0205 (4)	0.0012 (3)	−0.0034 (3)	0.0050 (3)
O3	0.0140 (4)	0.0235 (4)	0.0401 (6)	−0.0072 (3)	−0.0080 (4)	0.0150 (4)
N1	0.0148 (4)	0.0163 (4)	0.0198 (4)	−0.0041 (3)	0.0003 (3)	−0.0103 (3)
N2	0.0155 (4)	0.0181 (4)	0.0135 (4)	−0.0043 (3)	0.0004 (3)	−0.0073 (3)
C1	0.0097 (3)	0.0108 (4)	0.0131 (4)	−0.0009 (3)	−0.0008 (3)	−0.0041 (3)
C2	0.0104 (4)	0.0126 (4)	0.0162 (4)	−0.0023 (3)	−0.0012 (3)	−0.0058 (3)
C3	0.0126 (4)	0.0116 (4)	0.0155 (4)	−0.0019 (3)	−0.0024 (3)	−0.0047 (3)
C4	0.0120 (4)	0.0142 (4)	0.0150 (4)	−0.0018 (3)	−0.0005 (3)	−0.0058 (3)
C5	0.0109 (4)	0.0143 (4)	0.0143 (4)	−0.0017 (3)	−0.0002 (3)	−0.0054 (3)
C6	0.0094 (3)	0.0113 (4)	0.0132 (4)	−0.0014 (3)	−0.0015 (3)	−0.0034 (3)
C7	0.0092 (3)	0.0106 (4)	0.0119 (4)	−0.0011 (3)	−0.0016 (3)	−0.0022 (3)
C8	0.0106 (4)	0.0112 (4)	0.0118 (4)	−0.0019 (3)	−0.0017 (3)	−0.0026 (3)
C9	0.0116 (4)	0.0114 (4)	0.0128 (4)	−0.0022 (3)	−0.0026 (3)	−0.0026 (3)
C10	0.0133 (4)	0.0121 (4)	0.0123 (4)	−0.0023 (3)	−0.0031 (3)	−0.0030 (3)
C11	0.0136 (4)	0.0126 (4)	0.0115 (4)	−0.0019 (3)	−0.0010 (3)	−0.0032 (3)
C12	0.0129 (4)	0.0138 (4)	0.0135 (4)	−0.0039 (3)	0.0007 (3)	−0.0052 (3)
C13	0.0112 (4)	0.0115 (4)	0.0127 (4)	−0.0025 (3)	−0.0015 (3)	−0.0038 (3)
C14	0.0171 (5)	0.0222 (5)	0.0207 (5)	−0.0045 (4)	0.0030 (4)	−0.0129 (4)
C15	0.0174 (4)	0.0168 (4)	0.0149 (4)	−0.0039 (3)	−0.0038 (3)	−0.0067 (3)
C16	0.0095 (3)	0.0114 (4)	0.0114 (4)	−0.0020 (3)	−0.0014 (3)	−0.0028 (3)
C17	0.0099 (4)	0.0109 (4)	0.0135 (4)	−0.0015 (3)	−0.0016 (3)	−0.0020 (3)
C18	0.0097 (4)	0.0142 (4)	0.0168 (4)	−0.0018 (3)	−0.0015 (3)	−0.0029 (3)
C19	0.0122 (4)	0.0149 (4)	0.0153 (4)	−0.0037 (3)	−0.0001 (3)	−0.0034 (3)
C20	0.0152 (4)	0.0147 (4)	0.0144 (4)	−0.0045 (3)	−0.0019 (3)	0.0005 (3)
C21	0.0121 (4)	0.0140 (4)	0.0158 (4)	−0.0018 (3)	−0.0031 (3)	−0.0002 (3)
C22	0.0124 (4)	0.0128 (4)	0.0167 (4)	−0.0012 (3)	−0.0042 (3)	−0.0002 (3)
C23	0.0200 (5)	0.0197 (5)	0.0199 (5)	0.0023 (4)	−0.0043 (4)	0.0049 (4)
C24	0.0158 (4)	0.0139 (4)	0.0206 (5)	−0.0046 (3)	−0.0018 (4)	−0.0065 (4)
C25	0.0188 (5)	0.0259 (6)	0.0337 (7)	−0.0029 (4)	−0.0078 (5)	−0.0030 (5)
C26	0.0152 (4)	0.0217 (5)	0.0186 (5)	−0.0044 (4)	0.0023 (4)	−0.0088 (4)
C27	0.0178 (5)	0.0290 (6)	0.0230 (5)	−0.0010 (4)	0.0017 (4)	−0.0134 (5)
N3	0.0356 (7)	0.0410 (8)	0.0433 (8)	−0.0075 (6)	0.0048 (6)	0.0053 (7)
C28	0.0311 (6)	0.0223 (6)	0.0233 (6)	−0.0063 (5)	−0.0045 (5)	0.0009 (4)
C29	0.0252 (6)	0.0370 (7)	0.0190 (5)	−0.0098 (5)	−0.0050 (4)	−0.0010 (5)

Geometric parameters (Å, º) top

Sn1—Cl3	2.4237 (3)	C14—H14A	0.9800
Sn1—Cl3ⁱ	2.4237 (3)	C14—H14B	0.9800
Sn1—Cl1ⁱ	2.4396 (3)	C14—H14C	0.9800
Sn1—Cl1	2.4396 (3)	C15—H15A	0.9800
Sn1—Cl2ⁱ	2.4454 (3)	C15—H15B	0.9800
Sn1—Cl2	2.4454 (3)	C15—H15C	0.9800
O1—C1	1.3618 (12)	C16—C21	1.3966 (15)
O1—C13	1.3632 (12)	C16—C17	1.4080 (14)
O2—C22	1.3417 (13)	C17—C18	1.4017 (14)
O2—C23	1.4479 (15)	C17—C22	1.4865 (15)
O3—C22	1.2078 (14)	C18—C19	1.3925 (15)
N1—C3	1.3443 (13)	C18—H18	0.9500
N1—C24	1.4583 (15)	C19—C20	1.3893 (16)
N1—H1N	0.81 (2)	C19—H19	0.9500
N2—C11	1.3553 (13)	C20—C21	1.3955 (15)
N2—C26	1.4613 (15)	C20—H20	0.9500
N2—H2N	0.86 (2)	C21—H21	0.9500
C1—C2	1.3802 (14)	C23—H23A	0.9800
C1—C6	1.4169 (14)	C23—H23B	0.9800
C2—C3	1.4099 (14)	C23—H23C	0.9800
C2—H2	0.9500	C24—C25	1.5201 (18)
C3—C4	1.4500 (15)	C24—H24A	0.9900
C4—C5	1.3673 (14)	C24—H24B	0.9900
C4—C14	1.5027 (15)	C25—H25A	0.9800
C5—C6	1.4252 (14)	C25—H25B	0.9800
C5—H5	0.9500	C25—H25C	0.9800
C6—C7	1.4008 (14)	C26—C27	1.5198 (16)
C7—C8	1.4109 (14)	C26—H26A	0.9900
C7—C16	1.4941 (14)	C26—H26B	0.9900
C8—C13	1.4128 (14)	C27—H27A	0.9800
C8—C9	1.4266 (14)	C27—H27B	0.9800
C9—C10	1.3727 (14)	C27—H27C	0.9800
C9—H9	0.9500	N3—C28	1.146 (2)
C10—C11	1.4442 (15)	C28—C29	1.450 (2)
C10—C15	1.5024 (14)	C29—H29A	0.9800
C11—C12	1.4043 (14)	C29—H29B	0.9800
C12—C13	1.3839 (14)	C29—H29C	0.9800
C12—H12	0.9500

Cl3—Sn1—Cl3ⁱ	180.0	H14A—C14—H14C	109.5
Cl3—Sn1—Cl1ⁱ	89.363 (10)	H14B—C14—H14C	109.5
Cl3ⁱ—Sn1—Cl1ⁱ	90.638 (10)	C10—C15—H15A	109.5
Cl3—Sn1—Cl1	90.638 (10)	C10—C15—H15B	109.5
Cl3ⁱ—Sn1—Cl1	89.362 (10)	H15A—C15—H15B	109.5
Cl1ⁱ—Sn1—Cl1	180.0	C10—C15—H15C	109.5
Cl3—Sn1—Cl2ⁱ	90.291 (10)	H15A—C15—H15C	109.5
Cl3ⁱ—Sn1—Cl2ⁱ	89.709 (10)	H15B—C15—H15C	109.5
Cl1ⁱ—Sn1—Cl2ⁱ	90.829 (10)	C21—C16—C17	119.27 (9)
Cl1—Sn1—Cl2ⁱ	89.170 (10)	C21—C16—C7	117.43 (9)
Cl3—Sn1—Cl2	89.709 (10)	C17—C16—C7	123.29 (9)
Cl3ⁱ—Sn1—Cl2	90.290 (10)	C18—C17—C16	119.71 (9)
Cl1ⁱ—Sn1—Cl2	89.171 (11)	C18—C17—C22	121.02 (9)
Cl1—Sn1—Cl2	90.830 (10)	C16—C17—C22	119.27 (9)
Cl2ⁱ—Sn1—Cl2	180.0	C19—C18—C17	120.52 (10)
C1—O1—C13	120.30 (8)	C19—C18—H18	119.7
C22—O2—C23	114.57 (9)	C17—C18—H18	119.7
C3—N1—C24	126.24 (9)	C20—C19—C18	119.63 (10)
C3—N1—H1N	118.0 (13)	C20—C19—H19	120.2
C24—N1—H1N	115.6 (13)	C18—C19—H19	120.2
C11—N2—C26	123.53 (9)	C19—C20—C21	120.47 (10)
C11—N2—H2N	118.5 (12)	C19—C20—H20	119.8
C26—N2—H2N	118.0 (12)	C21—C20—H20	119.8
O1—C1—C2	116.05 (9)	C20—C21—C16	120.40 (10)
O1—C1—C6	121.03 (9)	C20—C21—H21	119.8
C2—C1—C6	122.93 (9)	C16—C21—H21	119.8
C1—C2—C3	119.50 (9)	O3—C22—O2	122.39 (10)
C1—C2—H2	120.3	O3—C22—C17	124.24 (10)
C3—C2—H2	120.3	O2—C22—C17	113.37 (9)
N1—C3—C2	121.95 (10)	O2—C23—H23A	109.5
N1—C3—C4	118.77 (9)	O2—C23—H23B	109.5
C2—C3—C4	119.29 (9)	H23A—C23—H23B	109.5
C5—C4—C3	119.00 (9)	O2—C23—H23C	109.5
C5—C4—C14	121.49 (10)	H23A—C23—H23C	109.5
C3—C4—C14	119.51 (9)	H23B—C23—H23C	109.5
C4—C5—C6	122.88 (9)	N1—C24—C25	113.19 (10)
C4—C5—H5	118.6	N1—C24—H24A	108.9
C6—C5—H5	118.6	C25—C24—H24A	108.9
C7—C6—C1	119.38 (9)	N1—C24—H24B	108.9
C7—C6—C5	124.23 (9)	C25—C24—H24B	108.9
C1—C6—C5	116.38 (9)	H24A—C24—H24B	107.8
C6—C7—C8	118.96 (9)	C24—C25—H25A	109.5
C6—C7—C16	121.31 (9)	C24—C25—H25B	109.5
C8—C7—C16	119.63 (9)	H25A—C25—H25B	109.5
C7—C8—C13	119.28 (9)	C24—C25—H25C	109.5
C7—C8—C9	124.03 (9)	H25A—C25—H25C	109.5
C13—C8—C9	116.67 (9)	H25B—C25—H25C	109.5
C10—C9—C8	122.33 (9)	N2—C26—C27	110.50 (10)
C10—C9—H9	118.8	N2—C26—H26A	109.5
C8—C9—H9	118.8	C27—C26—H26A	109.5
C9—C10—C11	119.04 (9)	N2—C26—H26B	109.5
C9—C10—C15	121.00 (9)	C27—C26—H26B	109.5
C11—C10—C15	119.95 (9)	H26A—C26—H26B	108.1
N2—C11—C12	120.82 (10)	C26—C27—H27A	109.5
N2—C11—C10	119.37 (9)	C26—C27—H27B	109.5
C12—C11—C10	119.80 (9)	H27A—C27—H27B	109.5
C13—C12—C11	119.16 (9)	C26—C27—H27C	109.5
C13—C12—H12	120.4	H27A—C27—H27C	109.5
C11—C12—H12	120.4	H27B—C27—H27C	109.5
O1—C13—C12	115.99 (9)	N3—C28—C29	179.32 (18)
O1—C13—C8	121.03 (9)	C28—C29—H29A	109.5
C12—C13—C8	122.98 (9)	C28—C29—H29B	109.5
C4—C14—H14A	109.5	H29A—C29—H29B	109.5
C4—C14—H14B	109.5	C28—C29—H29C	109.5
H14A—C14—H14B	109.5	H29A—C29—H29C	109.5
C4—C14—H14C	109.5	H29B—C29—H29C	109.5

C13—O1—C1—C2	179.54 (9)	C9—C10—C11—C12	1.40 (15)
C13—O1—C1—C6	−0.75 (15)	C15—C10—C11—C12	−179.79 (10)
O1—C1—C2—C3	−178.69 (9)	N2—C11—C12—C13	177.80 (10)
C6—C1—C2—C3	1.61 (16)	C10—C11—C12—C13	−0.92 (16)
C24—N1—C3—C2	−4.43 (18)	C1—O1—C13—C12	−178.66 (9)
C24—N1—C3—C4	174.88 (11)	C1—O1—C13—C8	1.91 (15)
C1—C2—C3—N1	179.50 (10)	C11—C12—C13—O1	−179.22 (9)
C1—C2—C3—C4	0.18 (16)	C11—C12—C13—C8	0.19 (16)
N1—C3—C4—C5	179.10 (11)	C7—C8—C13—O1	−2.03 (15)
C2—C3—C4—C5	−1.56 (16)	C9—C8—C13—O1	179.45 (9)
N1—C3—C4—C14	−1.55 (16)	C7—C8—C13—C12	178.58 (10)
C2—C3—C4—C14	177.78 (11)	C9—C8—C13—C12	0.06 (15)
C3—C4—C5—C6	1.23 (17)	C6—C7—C16—C21	93.07 (12)
C14—C4—C5—C6	−178.10 (11)	C8—C7—C16—C21	−83.31 (12)
O1—C1—C6—C7	−0.26 (15)	C6—C7—C16—C17	−88.32 (13)
C2—C1—C6—C7	179.42 (10)	C8—C7—C16—C17	95.30 (12)
O1—C1—C6—C5	178.39 (9)	C21—C16—C17—C18	0.58 (15)
C2—C1—C6—C5	−1.93 (15)	C7—C16—C17—C18	−178.01 (9)
C4—C5—C6—C7	179.04 (10)	C21—C16—C17—C22	−179.32 (9)
C4—C5—C6—C1	0.46 (16)	C7—C16—C17—C22	2.09 (15)
C1—C6—C7—C8	0.11 (15)	C16—C17—C18—C19	−0.52 (15)
C5—C6—C7—C8	−178.42 (10)	C22—C17—C18—C19	179.38 (10)
C1—C6—C7—C16	−176.29 (9)	C17—C18—C19—C20	0.11 (16)
C5—C6—C7—C16	5.18 (16)	C18—C19—C20—C21	0.25 (16)
C6—C7—C8—C13	1.00 (15)	C19—C20—C21—C16	−0.19 (16)
C16—C7—C8—C13	177.46 (9)	C17—C16—C21—C20	−0.23 (15)
C6—C7—C8—C9	179.40 (10)	C7—C16—C21—C20	178.44 (10)
C16—C7—C8—C9	−4.14 (15)	C23—O2—C22—O3	2.09 (17)
C7—C8—C9—C10	−177.98 (10)	C23—O2—C22—C17	−178.43 (10)
C13—C8—C9—C10	0.46 (15)	C18—C17—C22—O3	179.92 (12)
C8—C9—C10—C11	−1.18 (15)	C16—C17—C22—O3	−0.18 (17)
C8—C9—C10—C15	−179.97 (10)	C18—C17—C22—O2	0.46 (15)
C26—N2—C11—C12	−4.18 (17)	C16—C17—C22—O2	−179.64 (9)
C26—N2—C11—C10	174.54 (10)	C3—N1—C24—C25	96.39 (14)
C9—C10—C11—N2	−177.33 (10)	C11—N2—C26—C27	−169.80 (11)
C15—C10—C11—N2	1.48 (15)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Cl2	0.81 (2)	2.61 (2)	3.3644 (10)	156 (2)
N2—H2N···Cl1ⁱⁱ	0.86 (2)	2.75 (2)	3.5603 (10)	159 (2)

Symmetry code: (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	(C₂₇H₂₉N₂O₃)₂[SnCl₆]·2C₂H₃N
M_r	1272.54
Crystal system, space group	Triclinic, P1
Temperature (K)	90
a, b, c (Å)	9.7871 (10), 11.7827 (11), 13.2893 (12)
α, β, γ (°)	80.583 (4), 77.309 (4), 82.467 (4)
V (Å³)	1467.7 (2)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.76
Crystal size (mm)	0.28 × 0.27 × 0.25

Data collection
Diffractometer	Nonius KappaCCD diffractometer with Oxford Cryostream
Absorption correction	Multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.815, 0.832
No. of measured, independent and observed [I > 2σ(I)] reflections	54250, 14412, 12969
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.843

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.073, 1.03
No. of reflections	14412
No. of parameters	362
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.74, −1.24

Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997).