Packing and polytypism in 1,10-phenanthrolin-1-ium (2-carboxyethyl)(2-carboxylatoethyl)dichloro­stannate(IV)

Somphon, W.; Haller, K.J.; Rae, A.D.; Ng, S.W.

doi:10.1107/S0108768106002461

Packing and polytypism in 1,10-phenanthrolin-1-ium (2-carboxyethyl)(2-carboxylatoethyl)dichlorostannate(IV)

W. Somphon, K. J. Haller, A. D. Rae and S. W. Ng

The 1:1 adduct of [SnCl₂(C₂H₄COOCH₃)₂] and 1,10-phenanthroline, (C₁₂H₈N₂), which was set aside for 25 years, when recrystallized from ethanol was found to be the salt [C₁₂H₉N₂]⁺·[SnCl₂(C₂H₄COO)(C₂H₄COOH)]⁻. The Sn^IV atom in the anion has pseudo-octahedral coordination with two cis Cl atoms, two C atoms and two O atoms trans to the Cl atoms. The possibility of alternative stacking of layers perpendicular to c* offers an explanation for observed twinning and polytypism. An ordered, untwinned, Z = 2 crystal structure was determined. Pairs of adjacent anions are linked together by strong intermolecular O—H

O⁻ hydrogen bonds, and the cation contains a strong intramolecular N—H

N hydrogen bond between its two N atoms. The protonated ring of the cation exhibits increased Lewis acidity and is linked into a network with the anions using a strong N—H

O and weak C—H

O and C—H

Cl interactions. The remaining rings of the cation form weaker C—H

O and C—H

Cl interactions. The cations stack in columns along a with an interplanar spacing of 3.24 Å for separations between cations inversion-related about (1, $1\over2$ , $1\over2$ ) and 3.34 Å for separations between cations inversion-related about ( $1\over2$ , $1\over2$ , $1\over2$ ).

Keywords: polytypism; twinning; stacking faults; supramolecular structure.

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Supporting information

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768106002461/bs5018sup1.cif
Contains datablock kh02d

CCDC reference: 605622

Computing details top

Data collection: Collect (Nonius BV, 1997-2000); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare, et al., 1999); program(s) used to refine structure: SHELXTL (Bruker AXS Inc. 1998); molecular graphics: ORTEP (Burnett & Johnson 1996; Farrugia 1997).

Figures top

1,10-Phenanthrolin-1-ium (2-Carboxyethyl)(2-carboxylatoethyl)dichlorostannate(IV) top

Crystal data top

C₁₂H₉N₂⁺·C₆H₉Cl₂O₄Sn⁻	Z = 2
M_r = 515.94	F(000) = 512
Triclinic, P1	D_x = 1.760 Mg m⁻³
a = 7.1204 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.5017 (2) Å	Cell parameters from 25992 reflections
c = 12.5780 (2) Å	θ = 2.9–29.6°
α = 114.4242 (11)°	µ = 1.61 mm⁻¹
β = 92.5620 (11)°	T = 200 K
γ = 104.3542 (12)°	Needle, transparent colorless
V = 973.78 (3) Å³	0.17 × 0.14 × 0.12 mm

Data collection top

Bruker Nonius KappaCCD diffractometer	5019 independent reflections
Radiation source: fine-focus sealed X-ray tube	4174 reflections with I > 2σ(I)
Horizonatlly mounted graphite crystal monochromator	R_int = 0.035
Detector resolution: 9 pixels mm^-1	θ_max = 28.7°, θ_min = 3.0°
ϕ scan plus ω scans with κ offsets	h = −9→9
Absorption correction: multi-scan SORTAV, (Blessing, 1995)	k = −16→16
T_min = 0.798, T_max = 0.824	l = −16→16
28062 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.059	w = 1/[σ²(F_o²) + (0.P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max = 0.003
5019 reflections	Δρ_max = 1.31 e Å⁻³
251 parameters	Δρ_min = −0.68 e Å⁻³
0 restraints

Crystal data top

C₁₂H₉N₂⁺·C₆H₉Cl₂O₄Sn⁻	γ = 104.3542 (12)°
M_r = 515.94	V = 973.78 (3) Å³
Triclinic, P1	Z = 2
a = 7.1204 (1) Å	Mo Kα radiation
b = 12.5017 (2) Å	µ = 1.61 mm⁻¹
c = 12.5780 (2) Å	T = 200 K
α = 114.4242 (11)°	0.17 × 0.14 × 0.12 mm
β = 92.5620 (11)°

Data collection top

Bruker Nonius KappaCCD diffractometer	5019 independent reflections
Absorption correction: multi-scan SORTAV, (Blessing, 1995)	4174 reflections with I > 2σ(I)
T_min = 0.798, T_max = 0.824	R_int = 0.035
28062 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.059	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	Δρ_max = 1.31 e Å⁻³
5019 reflections	Δρ_min = −0.68 e Å⁻³
251 parameters

Special details top

Experimental. The data crsytal was cut from a larger needle shaped crystal by cleaving along an obvious twin plane (reentrant angles), followed by cutting approximately perpendicular to the twin plane. The crystal was difficult to cut, and fragmented giving a somewhat irregular shaped data crystal.

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.

TABLE of Least Squares Planes (x,y,z in crystal coordinates) and deviations of individual atoms from the planes. Atoms used to define the planes are preceded with *. (Perpendicular contact distances are calculated to the 14 atom phenanthroline plane for the C—H···π bonds. The phenanthrolinium ions related by the centers at (0, 1/2, 1/2) overlap at the edges of the N containing rings, while the phenanthrolinium ions related by the centers at (1/2, 1/2, 1/2) overlap the faces of the N containing rings.

Plane 1: 14 Atom Phenanthronine Plane 6.580 (1) x + 1.570 (6) y − 3.774 (5) z = 3.856 (2) * 0.019 (2) C31 * −0.002 (2) C32 * −0.011 (2) C33 * 0.009 (2) N34 * 0.017 (2) C35 * 0.014 (2) C36 * −0.034 (2) C37 * −0.036 (2) C38 * 0.017 (2) C39 * 0.014 (2) C40 * −0.026 (2) N41 * −0.031 (2) C42 * 0.015 (2) C43 * 0.036 (2) C44 Rms deviation of fitted atoms = 0.022 Deviation of the hydrogen bonded to C41 − 0.100 (0.028) H41N Deviation of the C–H···pi bonded hydrogen atoms of the pi-pi stacks centers at: (0, 1/2, 1/2) (1/2, 1/2, 1/2) 3.277 (3) H33 2_766 − 3.235 (8) H41N 2_666 3.345 (8) H41N 2_766 − 3.366 (2) H43 2_666 3.309 (3) H42 2_766 − 3.399 (2) H44 2_666

Plane 2: 6 Atom Middle Ring Plane 6.524 (3) x + 1.826 (11) y − 3.878 (11) z = 3.924 (7) * −0.007 (2) C35 * 0.015 (2) C36 * −0.007 (2) C37 * −0.009 (2) C38 * 0.018 (2) C39 * −0.010 (2) C40 0.020 (4) C31 − 0.026 (4) C32 − 0.059 (4) C33 − 0.040 (3) N34 − 0.074 (3) N41 − 0.080 (4) C42 − 0.010 (4) C43 0.036 (4) C44 Rms deviation of fitted atoms = 0.012

Plane 3: 6 Atom Unprotonated Ring Plane 6.604 (3) x + 1.480 (12) y − 3.669 (12) z = 3.899 (8) * 0.007 (2) C31 * −0.001 (2) C32 * −0.006 (2) C33 * 0.005 (2) N34 * 0.001 (2) C35 * −0.007 (2) C36 − 0.069 (4) C37 − 0.079 (5) C38 − 0.022 (4) C39 − 0.011 (4) C40 − 0.047 (4) N41 − 0.059 (5) C42 − 0.027 (6) C43 − 0.011 (6) C44 Rms deviation of fitted atoms = 0.005

Plane 4: 6 Atom Protonated Ring Plane 6.640 (2) x + 1.288 (12) y − 3.627 (12) z = 3.821 (5) * −0.013 (2) C39 * 0.013 (2) C40 * −0.002 (2) N41 * −0.009 (2) C42 * 0.008 (2) C43 * 0.003 (2) C44 0.001 (5) C31 0.010 (6) C32 0.026 (5) C33 0.042 (4) N34 0.021 (4) C35 − 0.009 (4) C36 − 0.086 (4) C37 − 0.092 (4) C38 − 0.059 (9) H41N Rms deviation of fitted atoms = 0.009

Interplanar Angles: Phenanthroline Unprotonated Protonated Middle Ring 1.18 (8) 1.65 (10) 2.50 (10) Protonated Ring 1.32 (8) 0.90 (10) Unprotonated Ring 0.55 (8)

Refinement. Refinement on F² for ALL reflections. Weighted R-factors wR and all goodness of fit values S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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. xyz and U were refined for the OH and NH hydrogen atoms. The CH₂ and CH hydrogen atoms were included in the refinement as riding atom contributions with idealized geometry, and CH distances set at the temperature adjusted values of 0.99 Angstroms for the CH² H atoms and 0.95 Angstroms for the CH distances as defined within SHELXTL.

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

	x	y	z	U_iso*/U_eq
Sn1	0.40500 (2)	0.111904 (14)	0.817654 (13)	0.02452 (6)
Cl11	0.24231 (10)	0.04003 (6)	0.94939 (6)	0.04213 (16)
Cl12	0.40291 (10)	0.32885 (5)	0.92664 (5)	0.03442 (14)
O11	0.6070 (2)	0.17256 (16)	0.68119 (14)	0.0326 (4)
C11	0.7736 (3)	0.2339 (2)	0.7372 (2)	0.0264 (5)
O12	0.9075 (3)	0.29248 (17)	0.69688 (16)	0.0330 (4)
H12O	0.870 (5)	0.276 (3)	0.636 (3)	0.049 (7)*
C12	0.8357 (3)	0.2489 (2)	0.8595 (2)	0.0314 (5)
H12A	0.8293	0.3297	0.9186	0.038*
H12B	0.9737	0.2473	0.8683	0.038*
C13	0.7052 (3)	0.1477 (2)	0.8840 (2)	0.0305 (5)
H13A	0.7220	0.1730	0.9704	0.037*
H13B	0.7451	0.0718	0.8458	0.037*
O13	0.3818 (3)	−0.08906 (15)	0.69251 (14)	0.0316 (4)
C14	0.2685 (3)	−0.1283 (2)	0.5948 (2)	0.0254 (5)
O14	0.2180 (2)	−0.23959 (14)	0.51962 (14)	0.0293 (4)
C15	0.1926 (3)	−0.0373 (2)	0.5686 (2)	0.0266 (5)
H15A	0.0640	−0.0807	0.5153	0.032*
H15B	0.2853	−0.0018	0.5272	0.032*
C16	0.1690 (3)	0.0657 (2)	0.6813 (2)	0.0263 (5)
H16A	0.0418	0.0387	0.7050	0.032*
H16B	0.1709	0.1384	0.6676	0.032*
C31	0.8463 (4)	0.7657 (3)	0.7673 (3)	0.0414 (7)
H31	0.8537	0.8498	0.8105	0.050*
C32	0.8916 (4)	0.7009 (3)	0.8249 (3)	0.0428 (7)
H32	0.9292	0.7394	0.9085	0.051*
C33	0.8819 (4)	0.5779 (2)	0.7591 (2)	0.0353 (6)
H33	0.9128	0.5342	0.8005	0.042*
N34	0.8320 (3)	0.51821 (18)	0.64223 (17)	0.0294 (4)
C35	0.7857 (3)	0.5827 (2)	0.5861 (2)	0.0262 (5)
C36	0.7889 (3)	0.7064 (2)	0.6440 (2)	0.0333 (6)
C37	0.7293 (4)	0.7645 (2)	0.5768 (3)	0.0400 (7)
H37	0.7278	0.8474	0.6168	0.048*
C38	0.6753 (4)	0.7045 (2)	0.4584 (3)	0.0385 (6)
H38	0.6358	0.7455	0.4164	0.046*
C39	0.6767 (3)	0.5798 (2)	0.3949 (2)	0.0317 (6)
C40	0.7274 (3)	0.5197 (2)	0.4592 (2)	0.0260 (5)
N41	0.7171 (3)	0.39916 (19)	0.40163 (18)	0.0259 (4)
H41N	0.735 (4)	0.360 (3)	0.435 (3)	0.049 (7)*
C42	0.6642 (4)	0.3356 (2)	0.2841 (2)	0.0329 (6)
H42	0.6577	0.2511	0.2468	0.039*
C43	0.6189 (4)	0.3925 (3)	0.2167 (2)	0.0390 (6)
H43	0.5840	0.3477	0.1331	0.047*
C44	0.6244 (4)	0.5134 (3)	0.2712 (2)	0.0378 (6)
H44	0.5929	0.5527	0.2253	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.02707 (9)	0.02620 (9)	0.02103 (9)	0.00771 (7)	0.00218 (6)	0.01127 (7)
Cl11	0.0500 (4)	0.0443 (4)	0.0345 (3)	0.0064 (3)	0.0137 (3)	0.0231 (3)
Cl12	0.0443 (4)	0.0259 (3)	0.0296 (3)	0.0112 (3)	−0.0016 (3)	0.0091 (3)
O11	0.0277 (9)	0.0439 (10)	0.0232 (9)	0.0010 (8)	−0.0010 (7)	0.0177 (8)
C11	0.0275 (12)	0.0285 (13)	0.0237 (12)	0.0094 (10)	0.0045 (10)	0.0112 (10)
O12	0.0305 (10)	0.0394 (11)	0.0269 (10)	0.0017 (8)	0.0009 (8)	0.0176 (9)
C12	0.0257 (12)	0.0414 (15)	0.0256 (12)	0.0051 (11)	0.0006 (10)	0.0163 (11)
C13	0.0289 (13)	0.0406 (14)	0.0271 (13)	0.0111 (11)	0.0022 (10)	0.0196 (12)
O13	0.0379 (10)	0.0278 (9)	0.0247 (9)	0.0137 (8)	−0.0032 (7)	0.0060 (7)
C14	0.0268 (12)	0.0277 (12)	0.0232 (12)	0.0083 (10)	0.0054 (9)	0.0123 (10)
O14	0.0394 (10)	0.0243 (9)	0.0226 (8)	0.0101 (7)	0.0021 (7)	0.0087 (7)
C15	0.0311 (13)	0.0266 (12)	0.0219 (11)	0.0087 (10)	−0.0008 (10)	0.0109 (10)
C16	0.0261 (12)	0.0259 (12)	0.0268 (12)	0.0077 (9)	−0.0012 (10)	0.0119 (10)
C31	0.0332 (14)	0.0330 (14)	0.0455 (17)	0.0066 (11)	0.0061 (12)	0.0069 (13)
C32	0.0359 (15)	0.0448 (17)	0.0314 (14)	0.0063 (13)	−0.0015 (12)	0.0051 (13)
C33	0.0308 (14)	0.0424 (15)	0.0297 (14)	0.0079 (11)	−0.0001 (11)	0.0151 (12)
N34	0.0254 (10)	0.0331 (11)	0.0289 (11)	0.0067 (9)	0.0020 (8)	0.0141 (9)
C35	0.0206 (11)	0.0279 (12)	0.0309 (13)	0.0053 (9)	0.0057 (9)	0.0144 (11)
C36	0.0239 (12)	0.0317 (13)	0.0437 (15)	0.0065 (10)	0.0095 (11)	0.0165 (12)
C37	0.0330 (14)	0.0326 (14)	0.0625 (19)	0.0106 (11)	0.0153 (13)	0.0273 (14)
C38	0.0289 (13)	0.0434 (16)	0.0621 (19)	0.0140 (12)	0.0148 (13)	0.0385 (15)
C39	0.0204 (12)	0.0425 (15)	0.0448 (15)	0.0084 (10)	0.0091 (11)	0.0312 (13)
C40	0.0184 (11)	0.0319 (13)	0.0338 (13)	0.0062 (9)	0.0067 (9)	0.0205 (11)
N41	0.0264 (10)	0.0318 (11)	0.0269 (11)	0.0092 (9)	0.0049 (8)	0.0194 (9)
C42	0.0327 (14)	0.0388 (14)	0.0248 (12)	0.0054 (11)	0.0020 (10)	0.0151 (11)
C43	0.0361 (15)	0.0550 (18)	0.0293 (13)	0.0067 (13)	0.0015 (11)	0.0259 (13)
C44	0.0299 (13)	0.0571 (18)	0.0422 (16)	0.0120 (12)	0.0078 (12)	0.0370 (15)

Geometric parameters (Å, º) top

Sn1—C13	2.127 (2)	C31—C36	1.401 (4)
Sn1—C16	2.131 (2)	C32—C33	1.395 (4)
Sn1—O13	2.3060 (17)	C33—N34	1.326 (3)
Sn1—Cl11	2.4045 (6)	N34—C35	1.356 (3)
Sn1—Cl12	2.4864 (6)	C35—C36	1.404 (3)
Sn1—O11	2.5192 (18)	C35—C40	1.442 (3)
O11—C11	1.232 (3)	C36—C37	1.431 (4)
C11—O12	1.307 (3)	C37—C38	1.346 (4)
C11—C12	1.502 (3)	C38—C39	1.431 (4)
O12—H12O	0.72 (3)	C39—C40	1.400 (3)
C12—C13	1.524 (3)	C39—C44	1.405 (4)
O13—C14	1.272 (3)	C40—N41	1.356 (3)
C14—O14	1.262 (3)	N41—C42	1.337 (3)
C14—C15	1.515 (3)	N41—H41N	0.79 (3)
C15—C16	1.521 (3)	C42—C43	1.384 (3)
C31—C32	1.370 (4)	C43—C44	1.366 (4)

C13—Sn1—C16	153.22 (9)	C14—C15—C16	111.6 (2)
C13—Sn1—O13	91.47 (8)	C15—C16—Sn1	108.65 (14)
C16—Sn1—O13	77.42 (7)	C32—C31—C36	119.3 (3)
C13—Sn1—Cl11	101.30 (7)	C31—C32—C33	119.1 (3)
C16—Sn1—Cl11	102.65 (7)	N34—C33—C32	123.9 (2)
O13—Sn1—Cl11	88.45 (5)	C33—N34—C35	116.5 (2)
C13—Sn1—Cl12	94.67 (7)	N34—C35—C36	124.1 (2)
C16—Sn1—Cl12	94.47 (6)	N34—C35—C40	117.8 (2)
O13—Sn1—Cl12	171.40 (4)	C36—C35—C40	118.1 (2)
Cl11—Sn1—Cl12	96.24 (2)	C31—C36—C35	117.0 (2)
C13—Sn1—O11	72.78 (7)	C31—C36—C37	123.4 (2)
C16—Sn1—O11	82.30 (7)	C35—C36—C37	119.6 (2)
O13—Sn1—O11	87.19 (6)	C38—C37—C36	121.6 (3)
Cl11—Sn1—O11	172.54 (4)	C37—C38—C39	120.8 (2)
Cl12—Sn1—O11	88.87 (4)	C40—C39—C44	118.2 (2)
C11—O11—Sn1	107.83 (14)	C40—C39—C38	118.5 (2)
O11—C11—O12	123.2 (2)	C44—C39—C38	123.2 (2)
O11—C11—C12	121.8 (2)	N41—C40—C39	119.5 (2)
O12—C11—C12	115.0 (2)	N41—C40—C35	119.2 (2)
C11—O12—H12O	108 (3)	C39—C40—C35	121.3 (2)
C11—C12—C13	111.7 (2)	C42—N41—C40	122.1 (2)
C12—C13—Sn1	110.5 (2)	C42—N41—H41N	115 (2)
C14—O13—Sn1	112.33 (14)	C40—N41—H41N	123 (2)
O14—C14—O13	122.4 (2)	N41—C42—C43	120.2 (2)
O14—C14—C15	119.3 (2)	C44—C43—C42	119.6 (2)
O13—C14—C15	118.4 (2)	C43—C44—C39	120.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12O···O14ⁱ	0.72 (3)	1.86 (3)	2.579 (2)	177 (3)
N41—H41N···O14ⁱ	0.79 (3)	1.91 (3)	2.688 (2)	166 (3)
N41—H41N···N34	0.79 (3)	2.46 (3)	2.737 (3)	102 (2)
C42—H42···O13ⁱ	0.95	2.40	3.154 (3)	136
C43—H43···Cl12ⁱⁱ	0.95	2.74	3.578 (3)	148
C44—H44···Cl12ⁱⁱⁱ	0.95	2.86	3.785 (3)	165
C37—H37···O13^iv	0.95	2.86	3.458 (3)	123
C38—H38···O11ⁱⁱⁱ	0.95	2.70	3.596 (3)	158
C31—H31···Cl11^v	0.95	2.95	3.578 (3)	125
C31—H31···Cl11^vi	0.95	3.04	3.619 (3)	121
C32—H32···Cl11^v	0.95	3.18	3.691 (3)	116
C33—H33···O12	0.95	2.74	3.377 (3)	125

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y, z−1; (iii) −x+1, −y+1, −z+1; (iv) x, y+1, z; (v) −x+1, −y+1, −z+2; (vi) x+1, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₂H₉N₂⁺·C₆H₉Cl₂O₄Sn⁻
M_r	515.94
Crystal system, space group	Triclinic, P1
Temperature (K)	200
a, b, c (Å)	7.1204 (1), 12.5017 (2), 12.5780 (2)
α, β, γ (°)	114.4242 (11), 92.5620 (11), 104.3542 (12)
V (Å³)	973.78 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.61
Crystal size (mm)	0.17 × 0.14 × 0.12

Data collection
Diffractometer	Bruker Nonius KappaCCD diffractometer
Absorption correction	Multi-scan SORTAV, (Blessing, 1995)
T_min, T_max	0.798, 0.824
No. of measured, independent and observed [I > 2σ(I)] reflections	28062, 5019, 4174
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.675

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.059, 0.97
No. of reflections	5019
No. of parameters	251
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.31, −0.68

Computer programs: Collect (Nonius BV, 1997-2000), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare, et al., 1999), SHELXTL (Bruker AXS Inc. 1998), ORTEP (Burnett & Johnson 1996; Farrugia 1997).

Selected geometric parameters (Å, º) top

Sn1—C13	2.127 (2)	C31—C36	1.401 (4)
Sn1—C16	2.131 (2)	C32—C33	1.395 (4)
Sn1—O13	2.3060 (17)	C33—N34	1.326 (3)
Sn1—Cl11	2.4045 (6)	N34—C35	1.356 (3)
Sn1—Cl12	2.4864 (6)	C35—C36	1.404 (3)
Sn1—O11	2.5192 (18)	C35—C40	1.442 (3)
O11—C11	1.232 (3)	C36—C37	1.431 (4)
C11—O12	1.307 (3)	C37—C38	1.346 (4)
C11—C12	1.502 (3)	C38—C39	1.431 (4)
O12—H12O	0.72 (3)	C39—C40	1.400 (3)
C12—C13	1.524 (3)	C39—C44	1.405 (4)
O13—C14	1.272 (3)	C40—N41	1.356 (3)
C14—O14	1.262 (3)	N41—C42	1.337 (3)
C14—C15	1.515 (3)	N41—H41N	0.79 (3)
C15—C16	1.521 (3)	C42—C43	1.384 (3)
C31—C32	1.370 (4)	C43—C44	1.366 (4)

C13—Sn1—C16	153.22 (9)	C14—C15—C16	111.6 (2)
C13—Sn1—O13	91.47 (8)	C15—C16—Sn1	108.65 (14)
C16—Sn1—O13	77.42 (7)	C32—C31—C36	119.3 (3)
C13—Sn1—Cl11	101.30 (7)	C31—C32—C33	119.1 (3)
C16—Sn1—Cl11	102.65 (7)	N34—C33—C32	123.9 (2)
O13—Sn1—Cl11	88.45 (5)	C33—N34—C35	116.5 (2)
C13—Sn1—Cl12	94.67 (7)	N34—C35—C36	124.1 (2)
C16—Sn1—Cl12	94.47 (6)	N34—C35—C40	117.8 (2)
O13—Sn1—Cl12	171.40 (4)	C36—C35—C40	118.1 (2)
Cl11—Sn1—Cl12	96.24 (2)	C31—C36—C35	117.0 (2)
C13—Sn1—O11	72.78 (7)	C31—C36—C37	123.4 (2)
C16—Sn1—O11	82.30 (7)	C35—C36—C37	119.6 (2)
O13—Sn1—O11	87.19 (6)	C38—C37—C36	121.6 (3)
Cl11—Sn1—O11	172.54 (4)	C37—C38—C39	120.8 (2)
Cl12—Sn1—O11	88.87 (4)	C40—C39—C44	118.2 (2)
C11—O11—Sn1	107.83 (14)	C40—C39—C38	118.5 (2)
O11—C11—O12	123.2 (2)	C44—C39—C38	123.2 (2)
O11—C11—C12	121.8 (2)	N41—C40—C39	119.5 (2)
O12—C11—C12	115.0 (2)	N41—C40—C35	119.2 (2)
C11—O12—H12O	108 (3)	C39—C40—C35	121.3 (2)
C11—C12—C13	111.7 (2)	C42—N41—C40	122.1 (2)
C12—C13—Sn1	110.5 (2)	C42—N41—H41N	115 (2)
C14—O13—Sn1	112.33 (14)	C40—N41—H41N	123 (2)
O14—C14—O13	122.4 (2)	N41—C42—C43	120.2 (2)
O14—C14—C15	119.3 (2)	C44—C43—C42	119.6 (2)
O13—C14—C15	118.4 (2)	C43—C44—C39	120.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12O···O14ⁱ	0.72 (3)	1.86 (3)	2.579 (2)	177.3 (33)
N41—H41N···O14ⁱ	0.79 (3)	1.91 (3)	2.688 (2)	166.3 (30)
N41—H41N···N34	0.79 (3)	2.46 (3)	2.737 (3)	101.9 (24)
C42—H42···O13ⁱ	0.95	2.40	3.154 (3)	136.0
C43—H43···Cl12ⁱⁱ	0.95	2.74	3.578 (3)	147.8
C44—H44···Cl12ⁱⁱⁱ	0.95	2.86	3.785 (3)	165.4
C37—H37···O13^iv	0.95	2.86	3.458 (3)	122.5
C38—H38···O11ⁱⁱⁱ	0.95	2.70	3.596 (3)	158.4
C31—H31···Cl11^v	0.95	2.95	3.578 (3)	125.1
C31—H31···Cl11^vi	0.95	3.04	3.619 (3)	121.2
C32—H32···Cl11^v	0.95	3.18	3.691 (3)	116.4
C33—H33···O12	0.95	2.74	3.377 (3)	125.3

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y, z−1; (iii) −x+1, −y+1, −z+1; (iv) x, y+1, z; (v) −x+1, −y+1, −z+2; (vi) x+1, y+1, z.

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Packing and polytypism in 1,10-phenanthrolin-1-ium (2-carboxyethyl)(2-carboxylatoethyl)dichloro­stannate(IV)

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Packing and polytypism in 1,10-phenanthrolin-1-ium (2-carboxyethyl)(2-carboxylatoethyl)dichlorostannate(IV)