Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046272/xu2328sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046272/xu2328Isup2.hkl |
CCDC reference: 663659
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.008 Å
- R factor = 0.056
- wR factor = 0.181
- Data-to-parameter ratio = 16.7
checkCIF/PLATON results
No syntax errors found
Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.399 0.842 Tmin(prime) and Tmax expected: 0.781 0.836 RR(prime) = 0.507 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.50 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for Cl1
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for Cl1 - O1 .. 6.11 su PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl2 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Cd1 (2) 1.97 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 17
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 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 2 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
For the only reference in the literature to N-[2,3-dihydro-2-(3-pyridinyl)-1H-isoindol-1-ylidene]-3-pyridinamine, see Vanden Eynde et al. (1992). The title compound was synthesized using the same procedure as for the 4-pyridyl analogue (Mulyana et al., 2005); Mulyana et al. (2005) also report the crystal structure of the ethanol-coordinated Cd(NO3)2 adduct.
The ligand was synthesized from o-phthalaldehyde and 3-aminopyridine (in place of 4-aminopyridine) according to the procedure described by Mulyana et al. (2005). An aqueous solution (5 ml) of cadmium perchlorate hexahydrate (0.210 g, 0.5 mmol) was added dropwise to an methanol solution (15 ml) containing N-[2,3-dihydro-2-(3-pyridinyl)-1H-isoindol-1-ylidene]-3-pyridinamine (0.286 g, 1 mmol). The resulting mixture was heated for 0.5 h. Colorless prismatic crystals were obtained from the solution after several days.
The Cl–O distance in the free perchlorate was refined with a distance restraint of Cl–O = 1.440±0.005 Å and the C–O distance in the methanol molecule was restrained to 1.450±0.005 Å (somewhat tight restraints were used). The anisotropic displacement parameters of the methanol atoms were restrained to be nearly isotropic.
The carbon-bound H atoms were generated geometrically (C–H 0.93 – 0.96 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C). The water and methanolic H atoms were placed in chemically sensible positions on the basis of hydrogen bonding interactions but they were not refined; U(H) was set to 1.5Ueq(O).
The N-[2,3-dihydro-2-(4-pyridinyl)-1H-isoindol-1-ylidene]-4-pyridinamine N-heterocycle forms an ethanol-coordinated adduct with cadmium dinitrate; the compound exists as a linear chain as the ligand functions as a bridge through its pyridyl N-atoms (Mulyana et al., 2005). N-[2,3-Dihydro-2-(3-pyridinyl)-1H-isoindol-1-ylidene]-3-pyridinamine forms a 2:1 adduct with cadmium perchlorate, but the position of the donor pyridyl N-atoms restricts the formation of a chain structure.
The dinuclear dication in [Cd2(C17H14N4)4(H2O)2(ClO4)2] 2[ClO4].2(CH3OH) lies about a twofold rotation axis. Aside from the four N atoms, the Cd is also linked to the water and perchlorate O atoms, the O atoms being cis to each other in the octahedral geometry (Table 1). The charge is balanced by two perchlorate ions; these interact weakly with the coordinated water and free methanol molecules (Table 2).
For the only reference in the literature to N-[2,3-dihydro-2-(3-pyridinyl)-1H-isoindol-1-ylidene]-3-pyridinamine, see Vanden Eynde et al. (1992). The title compound was synthesized using the same procedure as for the 4-pyridyl analogue (Mulyana et al., 2005); Mulyana et al. (2005) also report the crystal structure of the ethanol-coordinated Cd(NO3)2 adduct.
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); 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).
[Cd2(ClO4)2(C17H14N4)4(H2O)2](ClO4)2·2CH4O | F(000) = 3792 |
Mr = 1868.04 | Dx = 1.618 Mg m−3 |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 36081 reflections |
a = 21.0869 (6) Å | θ = 3.0–27.5° |
b = 14.8065 (4) Å | µ = 0.78 mm−1 |
c = 24.5650 (6) Å | T = 295 K |
V = 7669.8 (4) Å3 | Prism, colorless |
Z = 4 | 0.31 × 0.26 × 0.23 mm |
Rigaku R-AXIS RAPID IP diffractometer | 8748 independent reflections |
Radiation source: fine-focus sealed tube | 4867 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.077 |
ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −27→27 |
Tmin = 0.399, Tmax = 0.842 | k = −19→17 |
70672 measured reflections | l = −31→31 |
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)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.181 | w = 1/[σ2(Fo2) + (0.0926P)2 + 0.6395P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
8748 reflections | Δρmax = 0.82 e Å−3 |
525 parameters | Δρmin = −0.92 e Å−3 |
17 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0010 (2) |
[Cd2(ClO4)2(C17H14N4)4(H2O)2](ClO4)2·2CH4O | V = 7669.8 (4) Å3 |
Mr = 1868.04 | Z = 4 |
Orthorhombic, Pbcn | Mo Kα radiation |
a = 21.0869 (6) Å | µ = 0.78 mm−1 |
b = 14.8065 (4) Å | T = 295 K |
c = 24.5650 (6) Å | 0.31 × 0.26 × 0.23 mm |
Rigaku R-AXIS RAPID IP diffractometer | 8748 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 4867 reflections with I > 2σ(I) |
Tmin = 0.399, Tmax = 0.842 | Rint = 0.077 |
70672 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 17 restraints |
wR(F2) = 0.181 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.82 e Å−3 |
8748 reflections | Δρmin = −0.92 e Å−3 |
525 parameters |
x | y | z | Uiso*/Ueq | ||
Cd1 | 0.635902 (17) | 0.65940 (2) | 0.627490 (13) | 0.05385 (17) | |
Cl1 | 0.74313 (8) | 0.47014 (11) | 0.60565 (7) | 0.0835 (4) | |
Cl2 | 0.53500 (9) | 0.81815 (11) | 0.36251 (6) | 0.0824 (4) | |
O1 | 0.7036 (2) | 0.5440 (3) | 0.58675 (14) | 0.0824 (12) | |
O2 | 0.7426 (3) | 0.4662 (4) | 0.66334 (17) | 0.1157 (17) | |
O3 | 0.7203 (3) | 0.3871 (3) | 0.5849 (2) | 0.1266 (19) | |
O4 | 0.8058 (3) | 0.4856 (4) | 0.5878 (3) | 0.157 (3) | |
O5 | 0.5253 (4) | 0.8874 (4) | 0.4008 (3) | 0.166 (3) | |
O6 | 0.5543 (4) | 0.8587 (5) | 0.3128 (2) | 0.163 (3) | |
O7 | 0.4781 (3) | 0.7685 (6) | 0.3600 (3) | 0.203 (4) | |
O8 | 0.5853 (3) | 0.7629 (4) | 0.3823 (3) | 0.161 (3) | |
O9 | 0.5898 (4) | 0.8544 (4) | 0.5059 (3) | 0.153 (3) | |
H9o | 0.5933 | 0.8495 | 0.4715 | 0.229* | |
O1w | 0.67378 (17) | 0.7619 (2) | 0.56473 (13) | 0.0669 (9) | |
H1w1 | 0.7050 | 0.7940 | 0.5754 | 0.100* | |
H1w2 | 0.6461 | 0.7963 | 0.5502 | 0.100* | |
N1 | 0.5972 (2) | 0.5502 (3) | 0.68868 (15) | 0.0577 (10) | |
N2 | 0.5722 (2) | 0.5292 (3) | 0.83597 (15) | 0.0610 (11) | |
N3 | 0.60584 (19) | 0.5596 (3) | 0.92480 (15) | 0.0568 (10) | |
N4 | 0.4370 (2) | 0.6175 (3) | 0.93989 (15) | 0.0571 (10) | |
N5 | 0.56585 (18) | 0.7712 (3) | 0.66228 (15) | 0.0519 (9) | |
N6 | 0.39646 (18) | 0.7952 (3) | 0.69501 (15) | 0.0555 (10) | |
N7 | 0.29018 (18) | 0.7710 (3) | 0.67160 (15) | 0.0543 (10) | |
N8 | 0.2817 (2) | 0.7036 (3) | 0.81592 (16) | 0.0630 (11) | |
C1 | 0.5938 (3) | 0.4629 (3) | 0.6737 (2) | 0.0652 (13) | |
H1 | 0.5983 | 0.4486 | 0.6371 | 0.078* | |
C2 | 0.5841 (3) | 0.3945 (4) | 0.7100 (2) | 0.0740 (15) | |
H2 | 0.5808 | 0.3351 | 0.6981 | 0.089* | |
C3 | 0.5791 (3) | 0.4154 (4) | 0.7651 (2) | 0.0703 (15) | |
H3 | 0.5733 | 0.3697 | 0.7906 | 0.084* | |
C4 | 0.5828 (2) | 0.5038 (3) | 0.78171 (18) | 0.0546 (11) | |
C5 | 0.5907 (2) | 0.5696 (3) | 0.74220 (18) | 0.0545 (11) | |
H5 | 0.5916 | 0.6298 | 0.7529 | 0.065* | |
C6 | 0.6173 (3) | 0.5363 (3) | 0.87058 (19) | 0.0557 (12) | |
C7 | 0.6870 (2) | 0.5257 (3) | 0.8650 (2) | 0.0593 (12) | |
C8 | 0.7249 (3) | 0.5074 (4) | 0.8197 (2) | 0.0717 (15) | |
H8 | 0.7072 | 0.4978 | 0.7855 | 0.086* | |
C9 | 0.7896 (3) | 0.5042 (4) | 0.8275 (3) | 0.0794 (17) | |
H9 | 0.8158 | 0.4915 | 0.7980 | 0.095* | |
C10 | 0.8163 (3) | 0.5192 (4) | 0.8776 (3) | 0.093 (2) | |
H10 | 0.8602 | 0.5174 | 0.8813 | 0.112* | |
C11 | 0.7794 (3) | 0.5368 (4) | 0.9225 (3) | 0.0842 (18) | |
H11 | 0.7976 | 0.5460 | 0.9565 | 0.101* | |
C12 | 0.7141 (3) | 0.5403 (3) | 0.9154 (2) | 0.0671 (14) | |
C13 | 0.6648 (3) | 0.5607 (4) | 0.9568 (2) | 0.0672 (14) | |
H13 | 0.6641 | 0.5151 | 0.9852 | 0.081* | |
H13B | 0.6718 | 0.6194 | 0.9733 | 0.081* | |
C14 | 0.5484 (2) | 0.5836 (3) | 0.94858 (18) | 0.0533 (11) | |
C15 | 0.5449 (3) | 0.6060 (3) | 1.00350 (19) | 0.0643 (13) | |
H15 | 0.5811 | 0.6041 | 1.0252 | 0.077* | |
C16 | 0.4877 (3) | 0.6309 (3) | 1.0255 (2) | 0.0665 (14) | |
H16 | 0.4845 | 0.6431 | 1.0625 | 0.080* | |
C17 | 0.4347 (3) | 0.6380 (3) | 0.9925 (2) | 0.0651 (14) | |
H17 | 0.3966 | 0.6575 | 1.0075 | 0.078* | |
C18 | 0.4921 (2) | 0.5902 (3) | 0.91875 (18) | 0.0538 (11) | |
H18 | 0.4930 | 0.5746 | 0.8821 | 0.065* | |
C19 | 0.5831 (2) | 0.8585 (3) | 0.6609 (2) | 0.0601 (13) | |
H19 | 0.6250 | 0.8727 | 0.6529 | 0.072* | |
C20 | 0.5412 (3) | 0.9274 (4) | 0.6710 (2) | 0.0672 (14) | |
H20 | 0.5552 | 0.9869 | 0.6709 | 0.081* | |
C21 | 0.4790 (2) | 0.9087 (3) | 0.68110 (19) | 0.0600 (12) | |
H21 | 0.4503 | 0.9552 | 0.6873 | 0.072* | |
C22 | 0.4592 (2) | 0.8191 (3) | 0.68203 (16) | 0.0502 (11) | |
C23 | 0.5045 (2) | 0.7530 (3) | 0.67357 (17) | 0.0507 (11) | |
H23 | 0.4921 | 0.6928 | 0.6758 | 0.061* | |
C24 | 0.3530 (2) | 0.7902 (3) | 0.65882 (18) | 0.0521 (11) | |
C25 | 0.3553 (2) | 0.8023 (3) | 0.59882 (18) | 0.0566 (12) | |
C26 | 0.4052 (3) | 0.8169 (4) | 0.5640 (2) | 0.0687 (14) | |
H26 | 0.4465 | 0.8206 | 0.5772 | 0.082* | |
C27 | 0.3930 (4) | 0.8260 (4) | 0.5089 (2) | 0.0832 (18) | |
H27 | 0.4262 | 0.8356 | 0.4847 | 0.100* | |
C28 | 0.3314 (4) | 0.8208 (4) | 0.4899 (2) | 0.097 (2) | |
H28 | 0.3239 | 0.8272 | 0.4528 | 0.116* | |
C29 | 0.2814 (4) | 0.8065 (4) | 0.5238 (2) | 0.0857 (19) | |
H29 | 0.2402 | 0.8047 | 0.5104 | 0.103* | |
C30 | 0.2936 (3) | 0.7948 (3) | 0.5790 (2) | 0.0650 (14) | |
C31 | 0.2486 (3) | 0.7760 (4) | 0.62388 (18) | 0.0658 (14) | |
H31 | 0.2178 | 0.8242 | 0.6276 | 0.079* | |
H31B | 0.2264 | 0.7194 | 0.6181 | 0.079* | |
C32 | 0.2651 (2) | 0.7455 (3) | 0.72242 (19) | 0.0552 (11) | |
C33 | 0.2017 (2) | 0.7243 (4) | 0.7285 (2) | 0.0661 (13) | |
H33 | 0.1740 | 0.7308 | 0.6993 | 0.079* | |
C34 | 0.1797 (3) | 0.6936 (4) | 0.7776 (3) | 0.0788 (16) | |
H34 | 0.1369 | 0.6800 | 0.7819 | 0.095* | |
C35 | 0.2207 (3) | 0.6831 (4) | 0.8204 (2) | 0.0742 (15) | |
H35 | 0.2054 | 0.6610 | 0.8533 | 0.089* | |
C36 | 0.3031 (2) | 0.7365 (3) | 0.76821 (18) | 0.0558 (11) | |
H36 | 0.3454 | 0.7541 | 0.7658 | 0.067* | |
C37 | 0.5692 (4) | 0.9435 (5) | 0.5193 (3) | 0.136 (3) | |
H37A | 0.5237 | 0.9447 | 0.5213 | 0.203* | |
H37B | 0.5832 | 0.9849 | 0.4917 | 0.203* | |
H37C | 0.5867 | 0.9609 | 0.5538 | 0.203* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cd1 | 0.0483 (2) | 0.0615 (3) | 0.0518 (2) | 0.00206 (16) | 0.00526 (15) | −0.00315 (15) |
Cl1 | 0.0760 (10) | 0.0842 (11) | 0.0903 (10) | 0.0239 (9) | 0.0060 (8) | 0.0004 (8) |
Cl2 | 0.0913 (12) | 0.0785 (10) | 0.0773 (9) | −0.0042 (9) | 0.0064 (8) | −0.0024 (7) |
O1 | 0.090 (3) | 0.083 (3) | 0.074 (2) | 0.048 (2) | 0.003 (2) | −0.0037 (19) |
O2 | 0.126 (4) | 0.143 (4) | 0.078 (3) | 0.018 (3) | −0.019 (3) | 0.010 (3) |
O3 | 0.154 (5) | 0.081 (3) | 0.145 (4) | 0.017 (3) | −0.030 (4) | −0.029 (3) |
O4 | 0.087 (4) | 0.156 (5) | 0.229 (7) | 0.043 (4) | 0.061 (4) | 0.057 (5) |
O5 | 0.188 (7) | 0.143 (5) | 0.165 (6) | 0.017 (5) | 0.012 (5) | −0.068 (5) |
O6 | 0.189 (7) | 0.193 (7) | 0.108 (4) | 0.027 (5) | 0.022 (5) | 0.048 (4) |
O7 | 0.175 (7) | 0.217 (9) | 0.218 (7) | −0.110 (7) | −0.058 (6) | 0.009 (6) |
O8 | 0.125 (5) | 0.157 (6) | 0.200 (6) | 0.055 (4) | 0.045 (4) | 0.088 (5) |
O9 | 0.195 (6) | 0.112 (4) | 0.151 (5) | −0.011 (4) | −0.085 (4) | 0.014 (3) |
O1w | 0.064 (2) | 0.069 (2) | 0.067 (2) | −0.0084 (18) | 0.0102 (17) | 0.0027 (17) |
N1 | 0.060 (3) | 0.058 (2) | 0.055 (2) | 0.006 (2) | 0.0026 (19) | 0.0016 (18) |
N2 | 0.055 (3) | 0.071 (3) | 0.057 (2) | 0.010 (2) | −0.0024 (19) | 0.0027 (19) |
N3 | 0.049 (2) | 0.067 (3) | 0.055 (2) | −0.003 (2) | −0.0071 (18) | 0.0079 (18) |
N4 | 0.061 (3) | 0.054 (2) | 0.056 (2) | 0.004 (2) | 0.0051 (19) | 0.0052 (18) |
N5 | 0.043 (2) | 0.053 (2) | 0.060 (2) | 0.0064 (18) | 0.0048 (17) | −0.0044 (17) |
N6 | 0.041 (2) | 0.073 (3) | 0.053 (2) | 0.002 (2) | −0.0021 (17) | 0.0018 (18) |
N7 | 0.043 (2) | 0.060 (2) | 0.060 (2) | 0.0029 (18) | −0.0110 (17) | −0.0008 (18) |
N8 | 0.049 (3) | 0.078 (3) | 0.062 (2) | 0.003 (2) | 0.0024 (19) | 0.004 (2) |
C1 | 0.071 (4) | 0.060 (3) | 0.065 (3) | 0.001 (3) | 0.009 (3) | −0.008 (2) |
C2 | 0.076 (4) | 0.058 (3) | 0.087 (4) | 0.002 (3) | 0.003 (3) | −0.011 (3) |
C3 | 0.071 (4) | 0.061 (3) | 0.080 (4) | 0.010 (3) | 0.004 (3) | 0.012 (3) |
C4 | 0.048 (3) | 0.063 (3) | 0.052 (2) | 0.002 (2) | −0.001 (2) | 0.002 (2) |
C5 | 0.050 (3) | 0.056 (3) | 0.058 (3) | 0.003 (2) | 0.006 (2) | −0.003 (2) |
C6 | 0.054 (3) | 0.052 (3) | 0.061 (3) | 0.004 (2) | 0.000 (2) | 0.016 (2) |
C7 | 0.048 (3) | 0.046 (3) | 0.083 (3) | 0.003 (2) | −0.002 (2) | 0.010 (2) |
C8 | 0.062 (4) | 0.065 (4) | 0.088 (4) | 0.005 (3) | 0.007 (3) | 0.011 (3) |
C9 | 0.055 (4) | 0.065 (4) | 0.118 (5) | 0.013 (3) | 0.015 (3) | 0.018 (3) |
C10 | 0.053 (4) | 0.067 (4) | 0.159 (7) | 0.002 (3) | −0.005 (4) | 0.020 (4) |
C11 | 0.059 (4) | 0.071 (4) | 0.123 (5) | 0.001 (3) | −0.023 (4) | −0.001 (3) |
C12 | 0.054 (3) | 0.054 (3) | 0.093 (4) | 0.004 (2) | −0.009 (3) | 0.010 (3) |
C13 | 0.058 (3) | 0.070 (3) | 0.073 (3) | −0.002 (3) | −0.019 (3) | 0.006 (3) |
C14 | 0.058 (3) | 0.048 (3) | 0.054 (3) | −0.003 (2) | −0.003 (2) | 0.009 (2) |
C15 | 0.075 (4) | 0.058 (3) | 0.060 (3) | −0.002 (3) | −0.011 (3) | 0.005 (2) |
C16 | 0.088 (4) | 0.060 (3) | 0.052 (3) | 0.008 (3) | 0.000 (3) | 0.001 (2) |
C17 | 0.077 (4) | 0.059 (3) | 0.059 (3) | 0.009 (3) | 0.008 (3) | 0.004 (2) |
C18 | 0.052 (3) | 0.059 (3) | 0.051 (2) | 0.002 (2) | 0.004 (2) | 0.007 (2) |
C19 | 0.049 (3) | 0.056 (3) | 0.076 (3) | 0.001 (2) | 0.005 (2) | 0.000 (2) |
C20 | 0.068 (4) | 0.057 (3) | 0.077 (3) | 0.002 (3) | 0.006 (3) | 0.003 (2) |
C21 | 0.052 (3) | 0.056 (3) | 0.072 (3) | 0.007 (2) | 0.004 (2) | 0.003 (2) |
C22 | 0.047 (3) | 0.062 (3) | 0.041 (2) | 0.003 (2) | −0.0047 (19) | 0.0064 (19) |
C23 | 0.044 (3) | 0.056 (3) | 0.052 (2) | 0.003 (2) | 0.0015 (19) | 0.002 (2) |
C24 | 0.052 (3) | 0.050 (3) | 0.054 (3) | 0.005 (2) | −0.008 (2) | 0.000 (2) |
C25 | 0.072 (4) | 0.050 (3) | 0.048 (2) | 0.004 (2) | −0.012 (2) | 0.001 (2) |
C26 | 0.084 (4) | 0.066 (3) | 0.057 (3) | −0.001 (3) | −0.006 (3) | 0.003 (2) |
C27 | 0.114 (5) | 0.080 (4) | 0.055 (3) | −0.001 (4) | −0.003 (3) | 0.005 (3) |
C28 | 0.145 (7) | 0.095 (5) | 0.051 (3) | −0.002 (5) | −0.029 (4) | 0.007 (3) |
C29 | 0.105 (5) | 0.085 (4) | 0.067 (4) | −0.006 (4) | −0.036 (4) | 0.003 (3) |
C30 | 0.079 (4) | 0.054 (3) | 0.062 (3) | 0.003 (3) | −0.024 (3) | −0.004 (2) |
C31 | 0.061 (3) | 0.065 (3) | 0.071 (3) | 0.006 (3) | −0.027 (3) | −0.006 (2) |
C32 | 0.048 (3) | 0.048 (3) | 0.069 (3) | 0.006 (2) | −0.003 (2) | −0.004 (2) |
C33 | 0.047 (3) | 0.073 (4) | 0.078 (3) | 0.003 (3) | −0.013 (3) | −0.001 (3) |
C34 | 0.048 (3) | 0.084 (4) | 0.105 (5) | −0.003 (3) | 0.007 (3) | 0.000 (3) |
C35 | 0.050 (3) | 0.089 (4) | 0.083 (4) | −0.004 (3) | 0.009 (3) | 0.006 (3) |
C36 | 0.046 (3) | 0.065 (3) | 0.057 (3) | 0.001 (2) | −0.005 (2) | 0.003 (2) |
C37 | 0.123 (6) | 0.141 (6) | 0.143 (6) | 0.005 (5) | −0.011 (5) | 0.021 (5) |
Cd1—O1 | 2.442 (3) | C9—C10 | 1.373 (8) |
Cd1—O1w | 2.306 (3) | C9—H9 | 0.9300 |
Cd1—N1 | 2.354 (4) | C10—C11 | 1.374 (9) |
Cd1—N4i | 2.343 (4) | C10—H10 | 0.9300 |
Cd1—N5 | 2.378 (4) | C11—C12 | 1.389 (8) |
Cd1—N8i | 2.319 (4) | C11—H11 | 0.9300 |
Cl1—O4 | 1.410 (6) | C12—C13 | 1.485 (8) |
Cl1—O3 | 1.415 (5) | C13—H13 | 0.9700 |
Cl1—O2 | 1.418 (4) | C13—H13B | 0.9700 |
Cl1—O1 | 1.450 (4) | C14—C15 | 1.391 (6) |
Cl2—O5 | 1.406 (4) | C14—C18 | 1.399 (7) |
Cl2—O7 | 1.408 (4) | C15—C16 | 1.373 (7) |
Cl2—O6 | 1.419 (4) | C15—H15 | 0.9300 |
Cl2—O8 | 1.425 (4) | C16—C17 | 1.383 (7) |
O9—C37 | 1.428 (5) | C16—H16 | 0.9300 |
O9—H9o | 0.85 | C17—H17 | 0.9300 |
O1w—H1w1 | 0.85 | C18—H18 | 0.9300 |
O1w—H1w2 | 0.85 | C19—C20 | 1.372 (7) |
N1—C1 | 1.344 (6) | C19—H19 | 0.9300 |
N1—C5 | 1.353 (5) | C20—C21 | 1.362 (7) |
N2—C6 | 1.280 (6) | C20—H20 | 0.9300 |
N2—C4 | 1.403 (6) | C21—C22 | 1.392 (7) |
N3—C14 | 1.391 (6) | C21—H21 | 0.9300 |
N3—C6 | 1.397 (6) | C22—C23 | 1.385 (6) |
N3—C13 | 1.472 (6) | C23—H23 | 0.9300 |
N4—C17 | 1.329 (6) | C24—C25 | 1.485 (7) |
N4—C18 | 1.334 (6) | C25—C26 | 1.372 (7) |
N4—Cd1i | 2.343 (4) | C25—C30 | 1.394 (7) |
N5—C19 | 1.342 (6) | C26—C27 | 1.385 (7) |
N5—C23 | 1.350 (6) | C26—H26 | 0.9300 |
N6—C24 | 1.279 (6) | C27—C28 | 1.382 (11) |
N6—C22 | 1.405 (6) | C27—H27 | 0.9300 |
N7—C24 | 1.391 (6) | C28—C29 | 1.360 (10) |
N7—C32 | 1.407 (6) | C28—H28 | 0.9300 |
N7—C31 | 1.466 (5) | C29—C30 | 1.393 (7) |
N8—C35 | 1.327 (7) | C29—H29 | 0.9300 |
N8—C36 | 1.347 (6) | C30—C31 | 1.481 (7) |
N8—Cd1i | 2.319 (4) | C31—H31 | 0.9700 |
C1—C2 | 1.364 (7) | C31—H31B | 0.9700 |
C1—H1 | 0.9300 | C32—C33 | 1.381 (7) |
C2—C3 | 1.393 (7) | C32—C36 | 1.387 (6) |
C2—H2 | 0.9300 | C33—C34 | 1.371 (8) |
C3—C4 | 1.373 (7) | C33—H33 | 0.9300 |
C3—H3 | 0.9300 | C34—C35 | 1.370 (8) |
C4—C5 | 1.385 (6) | C34—H34 | 0.9300 |
C5—H5 | 0.9300 | C35—H35 | 0.9300 |
C6—C7 | 1.484 (7) | C36—H36 | 0.9300 |
C7—C12 | 1.381 (7) | C37—H37A | 0.9600 |
C7—C8 | 1.397 (7) | C37—H37B | 0.9600 |
C8—C9 | 1.378 (8) | C37—H37C | 0.9600 |
C8—H8 | 0.9300 | ||
O1w—Cd1—N8i | 87.44 (14) | C7—C12—C13 | 110.9 (5) |
O1w—Cd1—N4i | 85.96 (13) | C11—C12—C13 | 128.0 (6) |
N8i—Cd1—N4i | 171.83 (14) | N3—C13—C12 | 102.9 (4) |
O1w—Cd1—N1 | 177.61 (12) | N3—C13—H13 | 111.2 |
N8i—Cd1—N1 | 94.06 (15) | C12—C13—H13 | 111.2 |
N4i—Cd1—N1 | 92.38 (14) | N3—C13—H13B | 111.2 |
O1w—Cd1—N5 | 89.83 (13) | C12—C13—H13B | 111.2 |
N8i—Cd1—N5 | 93.05 (14) | H13—C13—H13B | 109.1 |
N4i—Cd1—N5 | 91.76 (14) | N3—C14—C15 | 121.0 (4) |
N1—Cd1—N5 | 91.94 (14) | N3—C14—C18 | 122.5 (4) |
O1w—Cd1—O1 | 89.10 (13) | C15—C14—C18 | 116.5 (5) |
N8i—Cd1—O1 | 90.30 (15) | C16—C15—C14 | 119.5 (5) |
N4i—Cd1—O1 | 84.78 (14) | C16—C15—H15 | 120.3 |
N1—Cd1—O1 | 89.04 (14) | C14—C15—H15 | 120.3 |
N5—Cd1—O1 | 176.44 (13) | C15—C16—C17 | 120.0 (5) |
O4—Cl1—O3 | 110.3 (4) | C15—C16—H16 | 120.0 |
O4—Cl1—O2 | 109.0 (4) | C17—C16—H16 | 120.0 |
O3—Cl1—O2 | 108.7 (3) | N4—C17—C16 | 121.5 (5) |
O4—Cl1—O1 | 108.4 (3) | N4—C17—H17 | 119.2 |
O3—Cl1—O1 | 110.1 (3) | C16—C17—H17 | 119.2 |
O2—Cl1—O1 | 110.2 (3) | N4—C18—C14 | 123.8 (4) |
O5—Cl2—O7 | 106.6 (5) | N4—C18—H18 | 118.1 |
O5—Cl2—O6 | 107.9 (5) | C14—C18—H18 | 118.1 |
O7—Cl2—O6 | 115.3 (5) | N5—C19—C20 | 122.5 (5) |
O5—Cl2—O8 | 107.4 (5) | N5—C19—H19 | 118.7 |
O7—Cl2—O8 | 110.4 (5) | C20—C19—H19 | 118.7 |
O6—Cl2—O8 | 108.8 (4) | C21—C20—C19 | 120.1 (5) |
Cl1—O1—Cd1 | 137.1 (2) | C21—C20—H20 | 120.0 |
C37—O9—H9o | 109.4 | C19—C20—H20 | 120.0 |
Cd1—O1w—H1w1 | 115.3 | C20—C21—C22 | 119.1 (5) |
Cd1—O1w—H1w2 | 115.9 | C20—C21—H21 | 120.5 |
H1w1—O1w—H1w2 | 109.0 | C22—C21—H21 | 120.5 |
C1—N1—C5 | 117.7 (4) | C23—C22—C21 | 117.7 (4) |
C1—N1—Cd1 | 120.3 (3) | C23—C22—N6 | 120.4 (4) |
C5—N1—Cd1 | 120.6 (3) | C21—C22—N6 | 121.8 (4) |
C6—N2—C4 | 122.3 (4) | N5—C23—C22 | 123.4 (4) |
C14—N3—C6 | 127.9 (4) | N5—C23—H23 | 118.3 |
C14—N3—C13 | 120.6 (4) | C22—C23—H23 | 118.3 |
C6—N3—C13 | 111.5 (4) | N6—C24—N7 | 122.5 (4) |
C17—N4—C18 | 118.7 (4) | N6—C24—C25 | 131.2 (5) |
C17—N4—Cd1i | 127.0 (4) | N7—C24—C25 | 106.3 (4) |
C18—N4—Cd1i | 112.1 (3) | C26—C25—C30 | 120.8 (5) |
C19—N5—C23 | 117.2 (4) | C26—C25—C24 | 131.5 (5) |
C19—N5—Cd1 | 119.6 (3) | C30—C25—C24 | 107.8 (4) |
C23—N5—Cd1 | 122.0 (3) | C25—C26—C27 | 118.8 (6) |
C24—N6—C22 | 122.1 (4) | C25—C26—H26 | 120.6 |
C24—N7—C32 | 127.8 (4) | C27—C26—H26 | 120.6 |
C24—N7—C31 | 112.3 (4) | C28—C27—C26 | 120.0 (7) |
C32—N7—C31 | 119.9 (4) | C28—C27—H27 | 120.0 |
C35—N8—C36 | 118.7 (5) | C26—C27—H27 | 120.0 |
C35—N8—Cd1i | 127.7 (4) | C29—C28—C27 | 122.0 (6) |
C36—N8—Cd1i | 111.9 (3) | C29—C28—H28 | 119.0 |
N1—C1—C2 | 122.9 (5) | C27—C28—H28 | 119.0 |
N1—C1—H1 | 118.6 | C28—C29—C30 | 118.2 (6) |
C2—C1—H1 | 118.6 | C28—C29—H29 | 120.9 |
C1—C2—C3 | 118.8 (5) | C30—C29—H29 | 120.9 |
C1—C2—H2 | 120.6 | C29—C30—C25 | 120.2 (6) |
C3—C2—H2 | 120.6 | C29—C30—C31 | 129.0 (5) |
C4—C3—C2 | 119.7 (5) | C25—C30—C31 | 110.8 (4) |
C4—C3—H3 | 120.1 | N7—C31—C30 | 102.7 (4) |
C2—C3—H3 | 120.1 | N7—C31—H31 | 111.2 |
C3—C4—C5 | 118.0 (4) | C30—C31—H31 | 111.2 |
C3—C4—N2 | 121.9 (4) | N7—C31—H31B | 111.2 |
C5—C4—N2 | 119.8 (5) | C30—C31—H31B | 111.2 |
N1—C5—C4 | 122.9 (4) | H31—C31—H31B | 109.1 |
N1—C5—H5 | 118.5 | C33—C32—C36 | 116.7 (5) |
C4—C5—H5 | 118.5 | C33—C32—N7 | 121.3 (4) |
N2—C6—N3 | 121.6 (5) | C36—C32—N7 | 121.9 (4) |
N2—C6—C7 | 131.8 (5) | C34—C33—C32 | 119.9 (5) |
N3—C6—C7 | 106.6 (4) | C34—C33—H33 | 120.0 |
C12—C7—C8 | 120.6 (5) | C32—C33—H33 | 120.0 |
C12—C7—C6 | 108.1 (4) | C35—C34—C33 | 119.9 (5) |
C8—C7—C6 | 131.3 (5) | C35—C34—H34 | 120.0 |
C9—C8—C7 | 117.5 (6) | C33—C34—H34 | 120.0 |
C9—C8—H8 | 121.2 | N8—C35—C34 | 121.5 (5) |
C7—C8—H8 | 121.2 | N8—C35—H35 | 119.2 |
C10—C9—C8 | 121.8 (6) | C34—C35—H35 | 119.2 |
C10—C9—H9 | 119.1 | N8—C36—C32 | 123.1 (5) |
C8—C9—H9 | 119.1 | N8—C36—H36 | 118.4 |
C9—C10—C11 | 121.1 (6) | C32—C36—H36 | 118.4 |
C9—C10—H10 | 119.5 | O9—C37—H37A | 109.5 |
C11—C10—H10 | 119.5 | O9—C37—H37B | 109.5 |
C10—C11—C12 | 118.0 (6) | H37A—C37—H37B | 109.5 |
C10—C11—H11 | 121.0 | O9—C37—H37C | 109.5 |
C12—C11—H11 | 121.0 | H37A—C37—H37C | 109.5 |
C7—C12—C11 | 121.0 (6) | H37B—C37—H37C | 109.5 |
O4—Cl1—O1—Cd1 | −120.7 (5) | C13—N3—C14—C18 | 175.0 (4) |
O3—Cl1—O1—Cd1 | 118.4 (4) | N3—C14—C15—C16 | 178.8 (5) |
O2—Cl1—O1—Cd1 | −1.5 (5) | C18—C14—C15—C16 | 1.4 (7) |
O1w—Cd1—O1—Cl1 | 140.1 (4) | C14—C15—C16—C17 | −3.2 (8) |
N8i—Cd1—O1—Cl1 | 52.7 (4) | C18—N4—C17—C16 | −0.5 (7) |
N4i—Cd1—O1—Cl1 | −133.8 (4) | Cd1i—N4—C17—C16 | −162.4 (4) |
N1—Cd1—O1—Cl1 | −41.4 (4) | C15—C16—C17—N4 | 2.8 (8) |
N8i—Cd1—N1—C1 | −120.6 (4) | C17—N4—C18—C14 | −1.4 (7) |
N4i—Cd1—N1—C1 | 54.3 (4) | Cd1i—N4—C18—C14 | 163.0 (4) |
N5—Cd1—N1—C1 | 146.2 (4) | N3—C14—C18—N4 | −176.4 (4) |
O1—Cd1—N1—C1 | −30.4 (4) | C15—C14—C18—N4 | 1.0 (7) |
N8i—Cd1—N1—C5 | 45.4 (4) | C23—N5—C19—C20 | 0.6 (7) |
N4i—Cd1—N1—C5 | −139.6 (4) | Cd1—N5—C19—C20 | 167.9 (4) |
N5—Cd1—N1—C5 | −47.8 (4) | N5—C19—C20—C21 | −2.2 (8) |
O1—Cd1—N1—C5 | 135.6 (4) | C19—C20—C21—C22 | 1.2 (8) |
O1w—Cd1—N5—C19 | −31.4 (4) | C20—C21—C22—C23 | 1.3 (7) |
N8i—Cd1—N5—C19 | 56.0 (4) | C20—C21—C22—N6 | 176.6 (4) |
N4i—Cd1—N5—C19 | −117.4 (4) | C24—N6—C22—C23 | −96.3 (5) |
N1—Cd1—N5—C19 | 150.2 (4) | C24—N6—C22—C21 | 88.4 (6) |
O1w—Cd1—N5—C23 | 135.2 (3) | C19—N5—C23—C22 | 2.0 (6) |
N8i—Cd1—N5—C23 | −137.3 (3) | Cd1—N5—C23—C22 | −165.0 (3) |
N4i—Cd1—N5—C23 | 49.3 (3) | C21—C22—C23—N5 | −2.9 (6) |
N1—Cd1—N5—C23 | −43.2 (3) | N6—C22—C23—N5 | −178.4 (4) |
C5—N1—C1—C2 | 0.1 (8) | C22—N6—C24—N7 | −176.8 (4) |
Cd1—N1—C1—C2 | 166.6 (4) | C22—N6—C24—C25 | 2.9 (8) |
N1—C1—C2—C3 | −1.8 (9) | C32—N7—C24—N6 | −7.1 (8) |
C1—C2—C3—C4 | 1.2 (8) | C31—N7—C24—N6 | 175.5 (5) |
C2—C3—C4—C5 | 0.8 (8) | C32—N7—C24—C25 | 173.2 (4) |
C2—C3—C4—N2 | 174.0 (5) | C31—N7—C24—C25 | −4.3 (5) |
C6—N2—C4—C3 | 92.8 (6) | N6—C24—C25—C26 | 4.6 (9) |
C6—N2—C4—C5 | −94.2 (6) | N7—C24—C25—C26 | −175.7 (5) |
C1—N1—C5—C4 | 2.1 (7) | N6—C24—C25—C30 | −176.5 (5) |
Cd1—N1—C5—C4 | −164.3 (4) | N7—C24—C25—C30 | 3.2 (5) |
C3—C4—C5—N1 | −2.5 (7) | C30—C25—C26—C27 | 1.4 (8) |
N2—C4—C5—N1 | −175.8 (4) | C24—C25—C26—C27 | −179.8 (5) |
C4—N2—C6—N3 | −178.5 (4) | C25—C26—C27—C28 | 0.3 (9) |
C4—N2—C6—C7 | 3.1 (9) | C26—C27—C28—C29 | −0.2 (10) |
C14—N3—C6—N2 | −4.5 (8) | C27—C28—C29—C30 | −1.6 (10) |
C13—N3—C6—N2 | 178.3 (5) | C28—C29—C30—C25 | 3.2 (9) |
C14—N3—C6—C7 | 174.3 (4) | C28—C29—C30—C31 | −178.1 (6) |
C13—N3—C6—C7 | −2.9 (5) | C26—C25—C30—C29 | −3.2 (8) |
N2—C6—C7—C12 | −179.7 (5) | C24—C25—C30—C29 | 177.8 (5) |
N3—C6—C7—C12 | 1.6 (5) | C26—C25—C30—C31 | 178.0 (5) |
N2—C6—C7—C8 | 2.2 (10) | C24—C25—C30—C31 | −1.1 (6) |
N3—C6—C7—C8 | −176.4 (5) | C24—N7—C31—C30 | 3.5 (5) |
C12—C7—C8—C9 | 0.3 (8) | C32—N7—C31—C30 | −174.1 (4) |
C6—C7—C8—C9 | 178.2 (5) | C29—C30—C31—N7 | 179.9 (5) |
C7—C8—C9—C10 | −0.7 (9) | C25—C30—C31—N7 | −1.4 (6) |
C8—C9—C10—C11 | 1.0 (10) | C24—N7—C32—C33 | −176.9 (5) |
C9—C10—C11—C12 | −1.0 (9) | C31—N7—C32—C33 | 0.4 (7) |
C8—C7—C12—C11 | −0.3 (8) | C24—N7—C32—C36 | 0.2 (7) |
C6—C7—C12—C11 | −178.6 (5) | C31—N7—C32—C36 | 177.5 (4) |
C8—C7—C12—C13 | 178.5 (5) | C36—C32—C33—C34 | −1.8 (8) |
C6—C7—C12—C13 | 0.2 (6) | N7—C32—C33—C34 | 175.5 (5) |
C10—C11—C12—C7 | 0.6 (9) | C32—C33—C34—C35 | −0.8 (9) |
C10—C11—C12—C13 | −178.0 (5) | C36—N8—C35—C34 | 0.8 (9) |
C14—N3—C13—C12 | −174.5 (4) | Cd1i—N8—C35—C34 | −163.1 (4) |
C6—N3—C13—C12 | 2.9 (5) | C33—C34—C35—N8 | 1.4 (9) |
C7—C12—C13—N3 | −1.8 (6) | C35—N8—C36—C32 | −3.6 (8) |
C11—C12—C13—N3 | 176.9 (5) | Cd1i—N8—C36—C32 | 162.7 (4) |
C6—N3—C14—C15 | −179.3 (5) | C33—C32—C36—N8 | 4.1 (7) |
C13—N3—C14—C15 | −2.3 (7) | N7—C32—C36—N8 | −173.2 (4) |
C6—N3—C14—C18 | −2.0 (7) |
Symmetry code: (i) −x+1, y, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O3ii | 0.85 | 2.11 | 2.945 (6) | 167 |
O1w—H1w2···O9 | 0.85 | 1.83 | 2.665 (7) | 167 |
O9—H9o···O5 | 0.85 | 2.32 | 2.959 (9) | 132 |
Symmetry code: (ii) −x+3/2, y+1/2, z. |
Experimental details
Crystal data | |
Chemical formula | [Cd2(ClO4)2(C17H14N4)4(H2O)2](ClO4)2·2CH4O |
Mr | 1868.04 |
Crystal system, space group | Orthorhombic, Pbcn |
Temperature (K) | 295 |
a, b, c (Å) | 21.0869 (6), 14.8065 (4), 24.5650 (6) |
V (Å3) | 7669.8 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.78 |
Crystal size (mm) | 0.31 × 0.26 × 0.23 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID IP |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.399, 0.842 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 70672, 8748, 4867 |
Rint | 0.077 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.181, 1.09 |
No. of reflections | 8748 |
No. of parameters | 525 |
No. of restraints | 17 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.82, −0.92 |
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).
Cd1—O1 | 2.442 (3) | Cd1—N4i | 2.343 (4) |
Cd1—O1w | 2.306 (3) | Cd1—N5 | 2.378 (4) |
Cd1—N1 | 2.354 (4) | Cd1—N8i | 2.319 (4) |
Symmetry code: (i) −x+1, y, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O3ii | 0.85 | 2.11 | 2.945 (6) | 167 |
O1w—H1w2···O9 | 0.85 | 1.83 | 2.665 (7) | 167 |
O9—H9o···O5 | 0.85 | 2.32 | 2.959 (9) | 132 |
Symmetry code: (ii) −x+3/2, y+1/2, z. |
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The N-[2,3-dihydro-2-(4-pyridinyl)-1H-isoindol-1-ylidene]-4-pyridinamine N-heterocycle forms an ethanol-coordinated adduct with cadmium dinitrate; the compound exists as a linear chain as the ligand functions as a bridge through its pyridyl N-atoms (Mulyana et al., 2005). N-[2,3-Dihydro-2-(3-pyridinyl)-1H-isoindol-1-ylidene]-3-pyridinamine forms a 2:1 adduct with cadmium perchlorate, but the position of the donor pyridyl N-atoms restricts the formation of a chain structure.
The dinuclear dication in [Cd2(C17H14N4)4(H2O)2(ClO4)2] 2[ClO4].2(CH3OH) lies about a twofold rotation axis. Aside from the four N atoms, the Cd is also linked to the water and perchlorate O atoms, the O atoms being cis to each other in the octahedral geometry (Table 1). The charge is balanced by two perchlorate ions; these interact weakly with the coordinated water and free methanol molecules (Table 2).