Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811031461/xu5283sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536811031461/xu5283Isup2.hkl |
CCDC reference: 845226
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.005 Å
- R factor = 0.041
- wR factor = 0.095
- Data-to-parameter ratio = 17.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.965 PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ? PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 4 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 194
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 8 PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF .... ? PLAT154_ALERT_1_G The su's on the Cell Angles are Equal .......... 0.00300 Deg. PLAT432_ALERT_2_G Short Inter X...Y Contact O4 .. C23 .. 2.93 Ang. PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 4
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 4 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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
Stannic chloride pentahydrate (0.35 g, 1 mmol), 10-hydroxybenzo[h]quinoline (0.20 g, 1 mmol) and 2-methyl-8-hydroxyquinoline (0.16 g, 1 mmol) were loaded into a convection tube and the tube was filled with dry methanol and kept at 333 K. Yellow crystals were collected from the side arm after several days (in approximately yield 80%, m.p. 538 K).
Carbon-bound H-atoms were placed in calculated positions [C—H 0.95 to 0.98 Å, Uiso(H) 1.2 to 1.5Ueq(C)] and were included in the refinement in the riding model approximation.
The ammonium and hydroxy H-atoms were located in a difference Fourier map, and were refined with distance restraints of N–H 0.88±0.01, O–H 0.84±0.01 Å; their temperature factors were refined.
The final difference Fourier map had a peak as well as a hole in the vicinity ot Sn1.
Omitted from the refinement was the (0 0 2) reflection.
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).
Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of (C14H10NO)[SnCl4(C10H8NO)].2CH3OH, at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. |
(C13H10NO)[SnCl4(C10H8NO)]·2CH4O | Z = 2 |
Mr = 678.97 | F(000) = 680 |
Triclinic, P1 | Dx = 1.701 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5645 (2) Å | Cell parameters from 6565 reflections |
b = 10.1112 (3) Å | θ = 2.3–29.3° |
c = 17.7837 (5) Å | µ = 1.40 mm−1 |
α = 98.105 (3)° | T = 100 K |
β = 95.653 (3)° | Prism, yellow |
γ = 97.509 (3)° | 0.30 × 0.30 × 0.10 mm |
V = 1325.56 (6) Å3 |
Agilent SuperNova Dual diffractometer with an Atlas detector | 5871 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 5239 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.056 |
Detector resolution: 10.4041 pixels mm-1 | θmax = 27.5°, θmin = 2.5° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) | k = −10→12 |
Tmin = 0.678, Tmax = 0.873 | l = −22→23 |
10548 measured reflections |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0329P)2 + 1.5116P] where P = (Fo2 + 2Fc2)/3 |
5871 reflections | (Δ/σ)max = 0.001 |
340 parameters | Δρmax = 1.23 e Å−3 |
4 restraints | Δρmin = −1.14 e Å−3 |
(C13H10NO)[SnCl4(C10H8NO)]·2CH4O | γ = 97.509 (3)° |
Mr = 678.97 | V = 1325.56 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.5645 (2) Å | Mo Kα radiation |
b = 10.1112 (3) Å | µ = 1.40 mm−1 |
c = 17.7837 (5) Å | T = 100 K |
α = 98.105 (3)° | 0.30 × 0.30 × 0.10 mm |
β = 95.653 (3)° |
Agilent SuperNova Dual diffractometer with an Atlas detector | 5871 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) | 5239 reflections with I > 2σ(I) |
Tmin = 0.678, Tmax = 0.873 | Rint = 0.056 |
10548 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 4 restraints |
wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 1.23 e Å−3 |
5871 reflections | Δρmin = −1.14 e Å−3 |
340 parameters |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.86883 (3) | 0.09428 (2) | 0.789295 (13) | 0.01747 (8) | |
Cl1 | 0.86363 (16) | −0.14417 (9) | 0.78823 (6) | 0.0417 (3) | |
Cl2 | 0.63271 (12) | 0.06051 (9) | 0.68485 (5) | 0.02469 (19) | |
Cl3 | 0.66698 (12) | 0.09658 (10) | 0.88638 (5) | 0.0303 (2) | |
Cl4 | 1.10456 (13) | 0.09761 (11) | 0.70839 (5) | 0.0340 (2) | |
O1 | 0.8665 (3) | 0.2980 (2) | 0.78929 (13) | 0.0164 (5) | |
O2 | 0.3798 (4) | 0.4948 (3) | 0.64356 (15) | 0.0274 (6) | |
H2 | 0.453 (5) | 0.464 (4) | 0.672 (2) | 0.041* | |
O3 | 0.5605 (3) | 0.4044 (3) | 0.75020 (15) | 0.0261 (6) | |
H3 | 0.649 (4) | 0.363 (4) | 0.752 (3) | 0.039* | |
O4 | 0.4163 (4) | 0.7760 (3) | 0.73826 (19) | 0.0459 (8) | |
H4 | 0.507 (5) | 0.836 (4) | 0.749 (3) | 0.069* | |
N1 | 1.0833 (4) | 0.1902 (3) | 0.88721 (15) | 0.0165 (6) | |
N2 | 0.2612 (4) | 0.6931 (3) | 0.58555 (18) | 0.0226 (6) | |
H1 | 0.304 (5) | 0.673 (4) | 0.6302 (12) | 0.027* | |
C1 | 1.0870 (4) | 0.3279 (3) | 0.89787 (19) | 0.0164 (7) | |
C2 | 0.9706 (4) | 0.3813 (3) | 0.84513 (19) | 0.0165 (7) | |
C3 | 0.9725 (5) | 0.5190 (3) | 0.8541 (2) | 0.0210 (7) | |
H3A | 0.8964 | 0.5564 | 0.8197 | 0.025* | |
C4 | 1.0860 (5) | 0.6053 (4) | 0.9140 (2) | 0.0240 (8) | |
H4A | 1.0843 | 0.6999 | 0.9191 | 0.029* | |
C5 | 1.1982 (5) | 0.5561 (4) | 0.9646 (2) | 0.0229 (7) | |
H5 | 1.2740 | 0.6159 | 1.0043 | 0.028* | |
C6 | 1.2003 (4) | 0.4154 (3) | 0.95736 (19) | 0.0192 (7) | |
C7 | 1.3109 (5) | 0.3538 (4) | 1.0069 (2) | 0.0234 (8) | |
H7 | 1.3881 | 0.4078 | 1.0484 | 0.028* | |
C8 | 1.3067 (5) | 0.2178 (4) | 0.9950 (2) | 0.0254 (8) | |
H8 | 1.3821 | 0.1773 | 1.0281 | 0.031* | |
C9 | 1.1914 (5) | 0.1355 (4) | 0.9339 (2) | 0.0213 (7) | |
C10 | 1.1918 (6) | −0.0137 (4) | 0.9208 (2) | 0.0320 (9) | |
H10A | 1.2077 | −0.0433 | 0.8673 | 0.048* | |
H10B | 1.0775 | −0.0596 | 0.9321 | 0.048* | |
H10C | 1.2907 | −0.0360 | 0.9543 | 0.048* | |
C11 | 0.2292 (4) | 0.6061 (4) | 0.5177 (2) | 0.0189 (7) | |
C12 | 0.2715 (4) | 0.4711 (4) | 0.5116 (2) | 0.0202 (7) | |
C13 | 0.3479 (4) | 0.4138 (4) | 0.5739 (2) | 0.0215 (7) | |
C14 | 0.3861 (5) | 0.2837 (4) | 0.5632 (2) | 0.0245 (8) | |
H14 | 0.4354 | 0.2465 | 0.6053 | 0.029* | |
C15 | 0.3524 (5) | 0.2065 (4) | 0.4906 (2) | 0.0256 (8) | |
H15 | 0.3810 | 0.1171 | 0.4835 | 0.031* | |
C16 | 0.2783 (5) | 0.2574 (4) | 0.4289 (2) | 0.0256 (8) | |
H16 | 0.2563 | 0.2032 | 0.3798 | 0.031* | |
C17 | 0.2354 (4) | 0.3891 (4) | 0.4384 (2) | 0.0214 (7) | |
C18 | 0.1589 (5) | 0.4437 (4) | 0.3745 (2) | 0.0263 (8) | |
H18 | 0.1362 | 0.3889 | 0.3256 | 0.032* | |
C19 | 0.1186 (5) | 0.5699 (4) | 0.3819 (2) | 0.0262 (8) | |
H19 | 0.0654 | 0.6017 | 0.3385 | 0.031* | |
C20 | 0.1542 (4) | 0.6568 (4) | 0.4535 (2) | 0.0222 (7) | |
C21 | 0.1174 (5) | 0.7900 (4) | 0.4624 (2) | 0.0295 (9) | |
H21 | 0.0681 | 0.8246 | 0.4193 | 0.035* | |
C22 | 0.1518 (5) | 0.8716 (4) | 0.5327 (2) | 0.0288 (8) | |
H22 | 0.1253 | 0.9615 | 0.5388 | 0.035* | |
C23 | 0.2259 (5) | 0.8189 (4) | 0.5943 (2) | 0.0290 (8) | |
H23 | 0.2517 | 0.8735 | 0.6432 | 0.035* | |
C24 | 0.4551 (6) | 0.3602 (4) | 0.8063 (2) | 0.0329 (9) | |
H24A | 0.5270 | 0.3807 | 0.8566 | 0.049* | |
H24B | 0.4163 | 0.2626 | 0.7935 | 0.049* | |
H24C | 0.3496 | 0.4069 | 0.8075 | 0.049* | |
C25 | 0.4131 (7) | 0.7114 (5) | 0.8025 (2) | 0.0414 (10) | |
H25A | 0.5218 | 0.6691 | 0.8094 | 0.062* | |
H25B | 0.3070 | 0.6420 | 0.7955 | 0.062* | |
H25C | 0.4083 | 0.7777 | 0.8479 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.02318 (13) | 0.01235 (12) | 0.01641 (13) | 0.00327 (9) | −0.00053 (9) | 0.00207 (8) |
Cl1 | 0.0566 (7) | 0.0134 (4) | 0.0472 (6) | 0.0041 (4) | −0.0256 (5) | 0.0014 (4) |
Cl2 | 0.0283 (4) | 0.0200 (4) | 0.0237 (4) | 0.0035 (3) | −0.0062 (4) | 0.0027 (3) |
Cl3 | 0.0279 (5) | 0.0373 (5) | 0.0282 (5) | −0.0008 (4) | 0.0084 (4) | 0.0156 (4) |
Cl4 | 0.0331 (5) | 0.0530 (6) | 0.0187 (4) | 0.0224 (5) | 0.0053 (4) | −0.0007 (4) |
O1 | 0.0193 (11) | 0.0139 (11) | 0.0167 (11) | 0.0049 (9) | 0.0023 (9) | 0.0027 (9) |
O2 | 0.0339 (15) | 0.0294 (15) | 0.0213 (14) | 0.0096 (12) | −0.0004 (12) | 0.0102 (11) |
O3 | 0.0230 (13) | 0.0351 (15) | 0.0266 (14) | 0.0133 (11) | 0.0089 (11) | 0.0143 (11) |
O4 | 0.0452 (18) | 0.049 (2) | 0.0390 (18) | −0.0141 (15) | −0.0075 (15) | 0.0209 (15) |
N1 | 0.0194 (13) | 0.0164 (14) | 0.0144 (14) | 0.0025 (11) | 0.0040 (11) | 0.0031 (11) |
N2 | 0.0192 (14) | 0.0256 (16) | 0.0242 (16) | 0.0015 (13) | 0.0018 (13) | 0.0104 (13) |
C1 | 0.0184 (15) | 0.0135 (15) | 0.0180 (16) | −0.0004 (13) | 0.0074 (13) | 0.0036 (12) |
C2 | 0.0167 (15) | 0.0177 (16) | 0.0167 (16) | 0.0029 (13) | 0.0083 (13) | 0.0039 (12) |
C3 | 0.0242 (17) | 0.0179 (17) | 0.0240 (18) | 0.0047 (14) | 0.0099 (15) | 0.0078 (14) |
C4 | 0.0272 (18) | 0.0135 (16) | 0.032 (2) | 0.0002 (14) | 0.0135 (16) | 0.0024 (14) |
C5 | 0.0218 (17) | 0.0196 (18) | 0.0244 (19) | −0.0027 (14) | 0.0071 (15) | −0.0042 (14) |
C6 | 0.0171 (16) | 0.0209 (17) | 0.0186 (17) | −0.0020 (13) | 0.0088 (14) | −0.0001 (13) |
C7 | 0.0196 (17) | 0.029 (2) | 0.0192 (18) | 0.0016 (15) | 0.0024 (14) | −0.0036 (14) |
C8 | 0.0246 (18) | 0.029 (2) | 0.0218 (18) | 0.0049 (16) | −0.0029 (15) | 0.0050 (15) |
C9 | 0.0249 (17) | 0.0204 (18) | 0.0192 (17) | 0.0047 (14) | 0.0020 (14) | 0.0047 (13) |
C10 | 0.040 (2) | 0.0217 (19) | 0.032 (2) | 0.0077 (17) | −0.0115 (18) | 0.0049 (16) |
C11 | 0.0128 (15) | 0.0243 (18) | 0.0214 (18) | 0.0013 (13) | 0.0046 (13) | 0.0090 (14) |
C12 | 0.0129 (15) | 0.0285 (19) | 0.0222 (18) | 0.0034 (14) | 0.0064 (14) | 0.0109 (14) |
C13 | 0.0182 (16) | 0.0268 (19) | 0.0217 (18) | 0.0034 (14) | 0.0051 (14) | 0.0089 (14) |
C14 | 0.0200 (17) | 0.029 (2) | 0.029 (2) | 0.0058 (15) | 0.0065 (15) | 0.0139 (15) |
C15 | 0.0227 (18) | 0.0247 (19) | 0.033 (2) | 0.0053 (15) | 0.0108 (16) | 0.0089 (15) |
C16 | 0.0238 (18) | 0.031 (2) | 0.0235 (19) | 0.0039 (16) | 0.0095 (15) | 0.0048 (15) |
C17 | 0.0166 (16) | 0.0291 (19) | 0.0215 (18) | 0.0039 (14) | 0.0079 (14) | 0.0100 (14) |
C18 | 0.0283 (19) | 0.036 (2) | 0.0170 (17) | 0.0049 (16) | 0.0064 (15) | 0.0081 (15) |
C19 | 0.0215 (17) | 0.040 (2) | 0.0220 (19) | 0.0068 (16) | 0.0067 (15) | 0.0156 (16) |
C20 | 0.0170 (16) | 0.030 (2) | 0.0236 (18) | 0.0041 (14) | 0.0071 (14) | 0.0135 (15) |
C21 | 0.0214 (18) | 0.038 (2) | 0.035 (2) | 0.0083 (17) | 0.0081 (17) | 0.0216 (18) |
C22 | 0.0288 (19) | 0.027 (2) | 0.034 (2) | 0.0071 (16) | 0.0080 (17) | 0.0113 (16) |
C23 | 0.0278 (19) | 0.024 (2) | 0.036 (2) | 0.0037 (16) | 0.0039 (17) | 0.0075 (16) |
C24 | 0.037 (2) | 0.034 (2) | 0.034 (2) | 0.0086 (18) | 0.0181 (18) | 0.0113 (17) |
C25 | 0.055 (3) | 0.037 (2) | 0.033 (2) | 0.006 (2) | 0.009 (2) | 0.0052 (19) |
Sn1—O1 | 2.063 (2) | C9—C10 | 1.494 (5) |
Sn1—N1 | 2.272 (3) | C10—H10A | 0.9800 |
Sn1—Cl4 | 2.3988 (10) | C10—H10B | 0.9800 |
Sn1—Cl2 | 2.4011 (8) | C10—H10C | 0.9800 |
Sn1—Cl1 | 2.4036 (9) | C11—C20 | 1.414 (5) |
Sn1—Cl3 | 2.4145 (9) | C11—C12 | 1.435 (5) |
O1—C2 | 1.324 (4) | C12—C17 | 1.422 (5) |
O2—C13 | 1.366 (4) | C12—C13 | 1.429 (5) |
O2—H2 | 0.843 (10) | C13—C14 | 1.375 (5) |
O3—C24 | 1.421 (5) | C14—C15 | 1.393 (5) |
O3—H3 | 0.835 (10) | C14—H14 | 0.9500 |
O4—C25 | 1.395 (5) | C15—C16 | 1.376 (5) |
O4—H4 | 0.838 (10) | C15—H15 | 0.9500 |
N1—C9 | 1.333 (4) | C16—C17 | 1.403 (5) |
N1—C1 | 1.374 (4) | C16—H16 | 0.9500 |
N2—C23 | 1.325 (5) | C17—C18 | 1.436 (5) |
N2—C11 | 1.369 (5) | C18—C19 | 1.342 (5) |
N2—H1 | 0.888 (10) | C18—H18 | 0.9500 |
C1—C6 | 1.413 (5) | C19—C20 | 1.423 (5) |
C1—C2 | 1.433 (5) | C19—H19 | 0.9500 |
C2—C3 | 1.377 (5) | C20—C21 | 1.401 (5) |
C3—C4 | 1.412 (5) | C21—C22 | 1.380 (6) |
C3—H3A | 0.9500 | C21—H21 | 0.9500 |
C4—C5 | 1.366 (5) | C22—C23 | 1.385 (5) |
C4—H4A | 0.9500 | C22—H22 | 0.9500 |
C5—C6 | 1.413 (5) | C23—H23 | 0.9500 |
C5—H5 | 0.9500 | C24—H24A | 0.9800 |
C6—C7 | 1.418 (5) | C24—H24B | 0.9800 |
C7—C8 | 1.358 (5) | C24—H24C | 0.9800 |
C7—H7 | 0.9500 | C25—H25A | 0.9800 |
C8—C9 | 1.415 (5) | C25—H25B | 0.9800 |
C8—H8 | 0.9500 | C25—H25C | 0.9800 |
O1—Sn1—N1 | 77.28 (9) | C9—C10—H10C | 109.5 |
O1—Sn1—Cl4 | 90.31 (7) | H10A—C10—H10C | 109.5 |
N1—Sn1—Cl4 | 86.85 (7) | H10B—C10—H10C | 109.5 |
O1—Sn1—Cl2 | 86.01 (6) | N2—C11—C20 | 116.6 (3) |
N1—Sn1—Cl2 | 163.26 (7) | N2—C11—C12 | 121.9 (3) |
Cl4—Sn1—Cl2 | 94.22 (3) | C20—C11—C12 | 121.5 (3) |
O1—Sn1—Cl1 | 178.56 (7) | C17—C12—C13 | 117.9 (3) |
N1—Sn1—Cl1 | 103.94 (7) | C17—C12—C11 | 117.7 (3) |
Cl4—Sn1—Cl1 | 90.53 (4) | C13—C12—C11 | 124.4 (3) |
Cl2—Sn1—Cl1 | 92.77 (3) | O2—C13—C14 | 122.6 (3) |
O1—Sn1—Cl3 | 90.14 (7) | O2—C13—C12 | 116.5 (3) |
N1—Sn1—Cl3 | 84.93 (7) | C14—C13—C12 | 120.8 (3) |
Cl4—Sn1—Cl3 | 171.46 (3) | C13—C14—C15 | 120.0 (3) |
Cl2—Sn1—Cl3 | 94.32 (3) | C13—C14—H14 | 120.0 |
Cl1—Sn1—Cl3 | 89.20 (4) | C15—C14—H14 | 120.0 |
C2—O1—Sn1 | 116.63 (19) | C16—C15—C14 | 121.1 (3) |
C13—O2—H2 | 109 (3) | C16—C15—H15 | 119.5 |
C24—O3—H3 | 105 (3) | C14—C15—H15 | 119.5 |
C25—O4—H4 | 104 (4) | C15—C16—C17 | 120.2 (3) |
C9—N1—C1 | 119.5 (3) | C15—C16—H16 | 119.9 |
C9—N1—Sn1 | 131.3 (2) | C17—C16—H16 | 119.9 |
C1—N1—Sn1 | 109.2 (2) | C16—C17—C12 | 119.9 (3) |
C23—N2—C11 | 124.4 (3) | C16—C17—C18 | 120.7 (3) |
C23—N2—H1 | 110 (3) | C12—C17—C18 | 119.3 (3) |
C11—N2—H1 | 126 (3) | C19—C18—C17 | 121.8 (3) |
N1—C1—C6 | 122.7 (3) | C19—C18—H18 | 119.1 |
N1—C1—C2 | 117.1 (3) | C17—C18—H18 | 119.1 |
C6—C1—C2 | 120.3 (3) | C18—C19—C20 | 121.1 (3) |
O1—C2—C3 | 122.2 (3) | C18—C19—H19 | 119.4 |
O1—C2—C1 | 119.5 (3) | C20—C19—H19 | 119.4 |
C3—C2—C1 | 118.3 (3) | C21—C20—C11 | 119.3 (3) |
C2—C3—C4 | 120.8 (3) | C21—C20—C19 | 122.2 (3) |
C2—C3—H3A | 119.6 | C11—C20—C19 | 118.5 (3) |
C4—C3—H3A | 119.6 | C22—C21—C20 | 121.0 (4) |
C5—C4—C3 | 121.7 (3) | C22—C21—H21 | 119.5 |
C5—C4—H4A | 119.2 | C20—C21—H21 | 119.5 |
C3—C4—H4A | 119.2 | C21—C22—C23 | 118.2 (4) |
C4—C5—C6 | 119.3 (3) | C21—C22—H22 | 120.9 |
C4—C5—H5 | 120.3 | C23—C22—H22 | 120.9 |
C6—C5—H5 | 120.3 | N2—C23—C22 | 120.6 (4) |
C1—C6—C5 | 119.6 (3) | N2—C23—H23 | 119.7 |
C1—C6—C7 | 116.4 (3) | C22—C23—H23 | 119.7 |
C5—C6—C7 | 123.9 (3) | O3—C24—H24A | 109.5 |
C8—C7—C6 | 120.1 (3) | O3—C24—H24B | 109.5 |
C8—C7—H7 | 120.0 | H24A—C24—H24B | 109.5 |
C6—C7—H7 | 120.0 | O3—C24—H24C | 109.5 |
C7—C8—C9 | 120.8 (3) | H24A—C24—H24C | 109.5 |
C7—C8—H8 | 119.6 | H24B—C24—H24C | 109.5 |
C9—C8—H8 | 119.6 | O4—C25—H25A | 109.5 |
N1—C9—C8 | 120.5 (3) | O4—C25—H25B | 109.5 |
N1—C9—C10 | 119.5 (3) | H25A—C25—H25B | 109.5 |
C8—C9—C10 | 119.9 (3) | O4—C25—H25C | 109.5 |
C9—C10—H10A | 109.5 | H25A—C25—H25C | 109.5 |
C9—C10—H10B | 109.5 | H25B—C25—H25C | 109.5 |
H10A—C10—H10B | 109.5 | ||
N1—Sn1—O1—C2 | −5.0 (2) | C1—N1—C9—C10 | −178.0 (3) |
Cl4—Sn1—O1—C2 | −91.7 (2) | Sn1—N1—C9—C10 | 5.3 (5) |
Cl2—Sn1—O1—C2 | 174.1 (2) | C7—C8—C9—N1 | −0.7 (6) |
Cl3—Sn1—O1—C2 | 79.8 (2) | C7—C8—C9—C10 | 178.6 (4) |
O1—Sn1—N1—C9 | −178.4 (3) | C23—N2—C11—C20 | 0.3 (5) |
Cl4—Sn1—N1—C9 | −87.4 (3) | C23—N2—C11—C12 | 179.5 (3) |
Cl2—Sn1—N1—C9 | 178.4 (2) | N2—C11—C12—C17 | −179.2 (3) |
Cl1—Sn1—N1—C9 | 2.4 (3) | C20—C11—C12—C17 | 0.0 (5) |
Cl3—Sn1—N1—C9 | 90.3 (3) | N2—C11—C12—C13 | 0.6 (5) |
O1—Sn1—N1—C1 | 4.6 (2) | C20—C11—C12—C13 | 179.8 (3) |
Cl4—Sn1—N1—C1 | 95.7 (2) | C17—C12—C13—O2 | −179.5 (3) |
Cl2—Sn1—N1—C1 | 1.5 (4) | C11—C12—C13—O2 | 0.7 (5) |
Cl1—Sn1—N1—C1 | −174.57 (19) | C17—C12—C13—C14 | 0.3 (5) |
Cl3—Sn1—N1—C1 | −86.7 (2) | C11—C12—C13—C14 | −179.4 (3) |
C9—N1—C1—C6 | −0.7 (5) | O2—C13—C14—C15 | −179.3 (3) |
Sn1—N1—C1—C6 | 176.6 (3) | C12—C13—C14—C15 | 0.8 (5) |
C9—N1—C1—C2 | 178.8 (3) | C13—C14—C15—C16 | −1.0 (5) |
Sn1—N1—C1—C2 | −3.8 (3) | C14—C15—C16—C17 | 0.0 (5) |
Sn1—O1—C2—C3 | −175.9 (2) | C15—C16—C17—C12 | 1.2 (5) |
Sn1—O1—C2—C1 | 4.7 (4) | C15—C16—C17—C18 | 179.7 (3) |
N1—C1—C2—O1 | −0.2 (4) | C13—C12—C17—C16 | −1.3 (5) |
C6—C1—C2—O1 | 179.4 (3) | C11—C12—C17—C16 | 178.4 (3) |
N1—C1—C2—C3 | −179.6 (3) | C13—C12—C17—C18 | −179.9 (3) |
C6—C1—C2—C3 | 0.0 (5) | C11—C12—C17—C18 | −0.1 (5) |
O1—C2—C3—C4 | −179.5 (3) | C16—C17—C18—C19 | −179.2 (3) |
C1—C2—C3—C4 | −0.2 (5) | C12—C17—C18—C19 | −0.7 (5) |
C2—C3—C4—C5 | 0.3 (5) | C17—C18—C19—C20 | 1.5 (6) |
C3—C4—C5—C6 | −0.3 (5) | N2—C11—C20—C21 | 0.1 (5) |
N1—C1—C6—C5 | 179.5 (3) | C12—C11—C20—C21 | −179.2 (3) |
C2—C1—C6—C5 | 0.0 (5) | N2—C11—C20—C19 | −179.9 (3) |
N1—C1—C6—C7 | −0.5 (5) | C12—C11—C20—C19 | 0.8 (5) |
C2—C1—C6—C7 | 180.0 (3) | C18—C19—C20—C21 | 178.4 (3) |
C4—C5—C6—C1 | 0.2 (5) | C18—C19—C20—C11 | −1.6 (5) |
C4—C5—C6—C7 | −179.8 (3) | C11—C20—C21—C22 | −0.6 (5) |
C1—C6—C7—C8 | 1.2 (5) | C19—C20—C21—C22 | 179.4 (4) |
C5—C6—C7—C8 | −178.9 (3) | C20—C21—C22—C23 | 0.9 (6) |
C6—C7—C8—C9 | −0.6 (5) | C11—N2—C23—C22 | 0.0 (6) |
C1—N1—C9—C8 | 1.3 (5) | C21—C22—C23—N2 | −0.5 (6) |
Sn1—N1—C9—C8 | −175.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3 | 0.84 (1) | 1.75 (2) | 2.570 (3) | 164 (5) |
O3—H3···O1 | 0.84 (1) | 1.94 (2) | 2.746 (3) | 162 (4) |
N2—H1···O4 | 0.89 (1) | 2.09 (3) | 2.816 (4) | 138 (3) |
Experimental details
Crystal data | |
Chemical formula | (C13H10NO)[SnCl4(C10H8NO)]·2CH4O |
Mr | 678.97 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 7.5645 (2), 10.1112 (3), 17.7837 (5) |
α, β, γ (°) | 98.105 (3), 95.653 (3), 97.509 (3) |
V (Å3) | 1325.56 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.40 |
Crystal size (mm) | 0.30 × 0.30 × 0.10 |
Data collection | |
Diffractometer | Agilent SuperNova Dual diffractometer with an Atlas detector |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2010) |
Tmin, Tmax | 0.678, 0.873 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10548, 5871, 5239 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.095, 1.11 |
No. of reflections | 5871 |
No. of parameters | 340 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.23, −1.14 |
Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3 | 0.84 (1) | 1.75 (2) | 2.570 (3) | 164 (5) |
O3—H3···O1 | 0.84 (1) | 1.94 (2) | 2.746 (3) | 162 (4) |
N2—H1···O4 | 0.89 (1) | 2.09 (3) | 2.816 (4) | 138 (3) |
We have been attempting to synthesize mixed-chelate tin(IV) compounds; in a recent study, we reacted stannic chloride with 8-hydroxyquinoline and 2-methyl-8-hydroxyquinoline (Vafaee et al., 2010). However, the reaction yielded 2-methyl-8-hydroxyquinolinium tetrachlorido(quinolin-8-olato)stannate as an acetonitrile solvate. The ligand that enages in coordination is the one that is less sterically crowded. A similar synthesis but with 10-hydroxybenzo[h]quinoline and 2-methyl-8-hydroxyquinoline in methanol medium yielded the di-solvated title salt (Scheme I, Fig. 1). Similarly, the less sterically crowded ligand engages in chelation, so that the more crowded ligand is now protonated. The SnIV atom shows octahedral SnNOCl4 coordination. The cation and anion are linked to the methanol molecules by O–H···O and N–H···O hydrogen bonds. One of the solvent molecules functions only as acceptor whereas the other functions both as a donor as well as acceptor.