The title compound, [Co(C16H21Cl2N2O)2]ClO4, possesses two independent half-molecules of the cation in the asymmetric unit. The symmetry of both cations is Ci. The CoIII atoms are six-coordinated by four N and two O atoms from two Schiff bases, forming slightly distorted octahedral coordination environments.
Supporting information
CCDC reference: 287701
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- Disorder in solvent or counterion
- R factor = 0.073
- wR factor = 0.160
- Data-to-parameter ratio = 17.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.63 Ratio
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.61 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C27
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl5
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 44.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT420_ALERT_2_C D-H Without Acceptor N4 - H4 ... ?
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl4 .. O5' .. 3.02 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
3,5-Dichlorosalicylaldehyde (0.1 mmol, 19.1 mg) and N-cyclohexyl-1,3-diaminopropane (0.1 mmol, 15.6 mg) were dissolved in MeOH (10 ml). The mixture was stirred for 15 min to give a clear yellow solution, then a MeOH solution of Co(ClO4)3·7H2O (0.1 mmol, 48.3 mg) was added. The mixture was stirred at room temperature for 15 min and filtered. The filtrate was kept in air for 3 d, and brown block-shaped crystals were formed at the bottom of the vessel on slow evaporation of the solvent.
Atoms H2 and H4 were located in a difference Fourier map and refined isotropically, with N—H distances restrained to 0.90 (1) Å and Uiso = 0.08 Å2. All other H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å, and with Uiso(H) = 1.2Ueq(C). The O atoms of the perchlorate anion are disordered over two distinct sites with occupancies of 0.581 (2) and 0.419 (2). The Cl—O and O···O distances in both disordered components were restrained to be equal.
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
Crystal data top
[Co(C16H21Cl2N2O)2]·ClO4 | F(000) = 1688 |
Mr = 814.88 | Dx = 1.501 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6581 reflections |
a = 16.136 (2) Å | θ = 2.2–25.2° |
b = 12.752 (2) Å | µ = 0.90 mm−1 |
c = 17.771 (2) Å | T = 298 K |
β = 99.486 (1)° | Block, brown |
V = 3606.7 (8) Å3 | 0.35 × 0.17 × 0.13 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 8227 independent reflections |
Radiation source: fine-focus sealed tube | 6373 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ω scan | θmax = 27.5°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −20→20 |
Tmin = 0.745, Tmax = 0.893 | k = −16→16 |
30380 measured reflections | l = −23→23 |
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)] = 0.073 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.160 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.15 | w = 1/[σ2(Fo2) + (0.0524P)2 + 4.3537P] where P = (Fo2 + 2Fc2)/3 |
8227 reflections | (Δ/σ)max < 0.001 |
479 parameters | Δρmax = 0.56 e Å−3 |
44 restraints | Δρmin = −0.38 e Å−3 |
Crystal data top
[Co(C16H21Cl2N2O)2]·ClO4 | V = 3606.7 (8) Å3 |
Mr = 814.88 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.136 (2) Å | µ = 0.90 mm−1 |
b = 12.752 (2) Å | T = 298 K |
c = 17.771 (2) Å | 0.35 × 0.17 × 0.13 mm |
β = 99.486 (1)° | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 8227 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 6373 reflections with I > 2σ(I) |
Tmin = 0.745, Tmax = 0.893 | Rint = 0.038 |
30380 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.073 | 44 restraints |
wR(F2) = 0.160 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.15 | Δρmax = 0.56 e Å−3 |
8227 reflections | Δρmin = −0.38 e Å−3 |
479 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 | Uiso*/Ueq | Occ. (<1) |
Co1 | 0.5000 | 0.5000 | 0.5000 | 0.03075 (16) | |
Co2 | 0.0000 | 1.0000 | 0.5000 | 0.03254 (17) | |
Cl1 | 0.26386 (8) | 0.89156 (11) | 0.63441 (8) | 0.0788 (4) | |
Cl2 | 0.34603 (10) | 1.29238 (14) | 0.70003 (9) | 0.0995 (6) | |
Cl3 | 0.43179 (10) | 0.62425 (12) | 0.73226 (7) | 0.0821 (4) | |
Cl4 | 0.10614 (10) | 0.53039 (15) | 0.63682 (11) | 0.1060 (6) | |
Cl5 | 0.14237 (8) | 0.36283 (11) | 0.32176 (8) | 0.0682 (3) | |
O1 | 0.11362 (16) | 0.98064 (18) | 0.54379 (14) | 0.0398 (6) | |
O2 | 0.45250 (16) | 0.5593 (2) | 0.58013 (13) | 0.0391 (6) | |
O3 | 0.1297 (9) | 0.2565 (6) | 0.3122 (8) | 0.152 (6) | 0.581 (13) |
O4 | 0.0955 (9) | 0.4111 (10) | 0.2609 (7) | 0.199 (9) | 0.581 (13) |
O5 | 0.1252 (7) | 0.3949 (10) | 0.3904 (5) | 0.128 (6) | 0.581 (13) |
O6 | 0.2270 (5) | 0.3794 (12) | 0.3196 (6) | 0.148 (7) | 0.581 (13) |
O3' | 0.1837 (7) | 0.4467 (8) | 0.2953 (6) | 0.085 (4) | 0.419 (13) |
O4' | 0.1857 (11) | 0.3234 (13) | 0.3880 (9) | 0.173 (9) | 0.419 (13) |
O5' | 0.0665 (9) | 0.4022 (10) | 0.3370 (14) | 0.184 (12) | 0.419 (13) |
O6' | 0.1234 (12) | 0.2846 (14) | 0.2692 (10) | 0.213 (16) | 0.419 (13) |
N1 | 0.02139 (19) | 1.1435 (2) | 0.47560 (17) | 0.0382 (7) | |
N2 | 0.0271 (2) | 0.9563 (3) | 0.39813 (17) | 0.0420 (7) | |
N3 | 0.39328 (19) | 0.5043 (2) | 0.43304 (16) | 0.0357 (6) | |
N4 | 0.5239 (2) | 0.6442 (2) | 0.46371 (17) | 0.0412 (7) | |
C1 | 0.1640 (2) | 1.0530 (3) | 0.57701 (19) | 0.0374 (8) | |
C2 | 0.2397 (3) | 1.0241 (3) | 0.6233 (2) | 0.0489 (10) | |
C3 | 0.2946 (3) | 1.0970 (4) | 0.6610 (2) | 0.0596 (13) | |
H3 | 0.3439 | 1.0757 | 0.6919 | 0.072* | |
C4 | 0.2751 (3) | 1.2016 (4) | 0.6523 (2) | 0.0594 (13) | |
C5 | 0.2056 (3) | 1.2348 (4) | 0.6058 (2) | 0.0546 (11) | |
H5 | 0.1948 | 1.3062 | 0.5993 | 0.066* | |
C6 | 0.1497 (2) | 1.1611 (3) | 0.5671 (2) | 0.0417 (9) | |
C7 | 0.0821 (2) | 1.1986 (3) | 0.5095 (2) | 0.0427 (9) | |
H7 | 0.0832 | 1.2690 | 0.4961 | 0.051* | |
C8 | −0.0328 (3) | 1.1904 (3) | 0.4090 (2) | 0.0507 (10) | |
H8A | −0.0131 | 1.2604 | 0.4002 | 0.061* | |
H8B | −0.0899 | 1.1959 | 0.4192 | 0.061* | |
C9 | −0.0317 (3) | 1.1232 (4) | 0.3383 (2) | 0.0593 (12) | |
H9A | −0.0853 | 1.0876 | 0.3261 | 0.071* | |
H9B | −0.0262 | 1.1691 | 0.2959 | 0.071* | |
C10 | 0.0363 (3) | 1.0433 (4) | 0.3452 (2) | 0.0562 (11) | |
H10A | 0.0380 | 1.0142 | 0.2950 | 0.067* | |
H10B | 0.0896 | 1.0778 | 0.3622 | 0.067* | |
C11 | 0.0934 (2) | 0.8711 (3) | 0.4020 (2) | 0.0403 (8) | |
H11 | 0.1007 | 0.8420 | 0.4537 | 0.048* | |
C12 | 0.1785 (3) | 0.9098 (4) | 0.3898 (3) | 0.0631 (12) | |
H12A | 0.1974 | 0.9651 | 0.4261 | 0.076* | |
H12B | 0.1745 | 0.9387 | 0.3388 | 0.076* | |
C13 | 0.2413 (3) | 0.8205 (5) | 0.3999 (4) | 0.0901 (19) | |
H13A | 0.2951 | 0.8455 | 0.3894 | 0.108* | |
H13B | 0.2492 | 0.7962 | 0.4523 | 0.108* | |
C14 | 0.2119 (4) | 0.7316 (5) | 0.3475 (4) | 0.098 (2) | |
H14A | 0.2522 | 0.6747 | 0.3565 | 0.118* | |
H14B | 0.2089 | 0.7545 | 0.2951 | 0.118* | |
C15 | 0.1272 (4) | 0.6926 (4) | 0.3592 (3) | 0.0782 (17) | |
H15A | 0.1310 | 0.6641 | 0.4103 | 0.094* | |
H15B | 0.1090 | 0.6369 | 0.3231 | 0.094* | |
C16 | 0.0623 (3) | 0.7825 (3) | 0.3481 (3) | 0.0585 (12) | |
H16A | 0.0546 | 0.8072 | 0.2958 | 0.070* | |
H16B | 0.0085 | 0.7574 | 0.3586 | 0.070* | |
C17 | 0.3748 (2) | 0.5528 (3) | 0.5899 (2) | 0.0409 (9) | |
C18 | 0.3525 (3) | 0.5803 (3) | 0.6611 (3) | 0.0553 (11) | |
C19 | 0.2714 (4) | 0.5732 (4) | 0.6745 (3) | 0.0707 (15) | |
H19 | 0.2590 | 0.5908 | 0.7222 | 0.085* | |
C20 | 0.2084 (3) | 0.5400 (4) | 0.6176 (3) | 0.0673 (14) | |
C21 | 0.2252 (3) | 0.5164 (3) | 0.5472 (3) | 0.0555 (11) | |
H21 | 0.1818 | 0.4966 | 0.5087 | 0.067* | |
C22 | 0.3080 (2) | 0.5217 (3) | 0.5322 (2) | 0.0419 (9) | |
C23 | 0.3215 (2) | 0.5092 (3) | 0.4553 (2) | 0.0409 (8) | |
H23 | 0.2740 | 0.5041 | 0.4179 | 0.049* | |
C24 | 0.3943 (3) | 0.5118 (3) | 0.3505 (2) | 0.0432 (9) | |
H24A | 0.3372 | 0.5170 | 0.3233 | 0.052* | |
H24B | 0.4195 | 0.4490 | 0.3333 | 0.052* | |
C25 | 0.4443 (3) | 0.6076 (4) | 0.3330 (2) | 0.0546 (11) | |
H25A | 0.4958 | 0.5838 | 0.3172 | 0.065* | |
H25B | 0.4120 | 0.6446 | 0.2903 | 0.065* | |
C26 | 0.4662 (3) | 0.6825 (3) | 0.3969 (2) | 0.0552 (11) | |
H26A | 0.4910 | 0.7441 | 0.3777 | 0.066* | |
H26B | 0.4146 | 0.7046 | 0.4136 | 0.066* | |
C27 | 0.5510 (2) | 0.7249 (3) | 0.5255 (2) | 0.0371 (8) | |
H27 | 0.5676 | 0.6860 | 0.5732 | 0.044* | |
C28 | 0.6282 (3) | 0.7827 (4) | 0.5100 (3) | 0.0611 (12) | |
H28A | 0.6147 | 0.8225 | 0.4631 | 0.073* | |
H28B | 0.6719 | 0.7327 | 0.5038 | 0.073* | |
C29 | 0.6599 (4) | 0.8566 (5) | 0.5758 (3) | 0.0831 (17) | |
H29A | 0.6804 | 0.8157 | 0.6211 | 0.100* | |
H29B | 0.7065 | 0.8975 | 0.5633 | 0.100* | |
C30 | 0.5916 (5) | 0.9298 (4) | 0.5923 (4) | 0.097 (2) | |
H30A | 0.6126 | 0.9715 | 0.6371 | 0.117* | |
H30B | 0.5765 | 0.9772 | 0.5496 | 0.117* | |
C31 | 0.5148 (4) | 0.8706 (4) | 0.6058 (3) | 0.0826 (17) | |
H31A | 0.4711 | 0.9200 | 0.6131 | 0.099* | |
H31B | 0.5283 | 0.8290 | 0.6518 | 0.099* | |
C32 | 0.4826 (3) | 0.7989 (3) | 0.5387 (3) | 0.0563 (11) | |
H32A | 0.4344 | 0.7595 | 0.5494 | 0.068* | |
H32B | 0.4649 | 0.8406 | 0.4932 | 0.068* | |
H2 | −0.0222 (17) | 0.927 (4) | 0.377 (3) | 0.080* | |
H4 | 0.570 (2) | 0.634 (4) | 0.442 (3) | 0.080* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co1 | 0.0352 (3) | 0.0304 (3) | 0.0268 (3) | −0.0033 (3) | 0.0056 (3) | 0.0014 (3) |
Co2 | 0.0376 (4) | 0.0286 (3) | 0.0297 (3) | −0.0012 (3) | 0.0004 (3) | 0.0030 (3) |
Cl1 | 0.0605 (7) | 0.0767 (9) | 0.0889 (9) | 0.0122 (6) | −0.0182 (7) | 0.0182 (7) |
Cl2 | 0.0873 (10) | 0.1170 (13) | 0.0863 (10) | −0.0608 (10) | −0.0087 (8) | −0.0174 (9) |
Cl3 | 0.1070 (11) | 0.0937 (10) | 0.0501 (7) | −0.0106 (8) | 0.0261 (7) | −0.0272 (7) |
Cl4 | 0.0724 (9) | 0.1263 (14) | 0.1361 (15) | 0.0153 (9) | 0.0673 (10) | 0.0199 (11) |
Cl5 | 0.0534 (7) | 0.0792 (9) | 0.0698 (8) | −0.0222 (6) | 0.0035 (6) | 0.0070 (7) |
O1 | 0.0427 (14) | 0.0320 (13) | 0.0411 (14) | 0.0007 (11) | −0.0039 (11) | 0.0009 (11) |
O2 | 0.0448 (15) | 0.0417 (15) | 0.0327 (13) | −0.0040 (12) | 0.0118 (11) | −0.0027 (11) |
O3 | 0.181 (12) | 0.056 (6) | 0.217 (16) | −0.010 (6) | 0.030 (12) | 0.012 (7) |
O4 | 0.237 (18) | 0.176 (12) | 0.140 (11) | 0.073 (12) | −0.100 (11) | 0.015 (9) |
O5 | 0.129 (10) | 0.186 (13) | 0.079 (6) | −0.077 (10) | 0.048 (6) | −0.011 (7) |
O6 | 0.086 (7) | 0.253 (16) | 0.111 (8) | −0.096 (9) | 0.037 (6) | −0.079 (10) |
O3' | 0.057 (7) | 0.124 (9) | 0.076 (7) | −0.012 (6) | 0.017 (5) | 0.029 (6) |
O4' | 0.147 (15) | 0.140 (14) | 0.205 (18) | 0.020 (11) | −0.046 (14) | 0.066 (13) |
O5' | 0.108 (12) | 0.125 (12) | 0.36 (3) | 0.027 (10) | 0.153 (17) | 0.036 (18) |
O6' | 0.163 (18) | 0.33 (4) | 0.152 (18) | −0.15 (2) | 0.031 (14) | −0.13 (2) |
N1 | 0.0463 (18) | 0.0300 (16) | 0.0375 (16) | 0.0009 (13) | 0.0045 (14) | 0.0056 (13) |
N2 | 0.052 (2) | 0.0385 (17) | 0.0341 (17) | 0.0014 (15) | 0.0040 (14) | 0.0014 (14) |
N3 | 0.0423 (17) | 0.0337 (15) | 0.0305 (15) | −0.0044 (13) | 0.0045 (12) | 0.0023 (12) |
N4 | 0.056 (2) | 0.0319 (16) | 0.0345 (16) | −0.0073 (15) | 0.0054 (14) | 0.0044 (13) |
C1 | 0.0390 (19) | 0.044 (2) | 0.0294 (18) | −0.0041 (16) | 0.0075 (15) | 0.0037 (15) |
C2 | 0.043 (2) | 0.062 (3) | 0.041 (2) | −0.0052 (19) | 0.0035 (17) | 0.0095 (19) |
C3 | 0.042 (2) | 0.097 (4) | 0.037 (2) | −0.016 (2) | −0.0037 (18) | 0.011 (2) |
C4 | 0.055 (3) | 0.075 (3) | 0.045 (2) | −0.036 (2) | 0.003 (2) | −0.002 (2) |
C5 | 0.057 (3) | 0.056 (3) | 0.052 (2) | −0.023 (2) | 0.012 (2) | −0.002 (2) |
C6 | 0.043 (2) | 0.045 (2) | 0.038 (2) | −0.0131 (17) | 0.0090 (16) | 0.0001 (17) |
C7 | 0.053 (2) | 0.0293 (18) | 0.048 (2) | −0.0059 (17) | 0.0145 (18) | 0.0028 (16) |
C8 | 0.059 (3) | 0.039 (2) | 0.051 (2) | 0.0027 (19) | 0.001 (2) | 0.0154 (18) |
C9 | 0.073 (3) | 0.060 (3) | 0.042 (2) | 0.008 (2) | 0.001 (2) | 0.019 (2) |
C10 | 0.071 (3) | 0.061 (3) | 0.038 (2) | 0.009 (2) | 0.013 (2) | 0.011 (2) |
C11 | 0.046 (2) | 0.039 (2) | 0.0349 (19) | 0.0037 (17) | 0.0032 (16) | −0.0003 (16) |
C12 | 0.051 (3) | 0.064 (3) | 0.077 (3) | −0.002 (2) | 0.014 (2) | 0.004 (3) |
C13 | 0.060 (3) | 0.089 (4) | 0.126 (5) | 0.020 (3) | 0.031 (3) | 0.010 (4) |
C14 | 0.128 (6) | 0.078 (4) | 0.099 (5) | 0.063 (4) | 0.051 (4) | 0.023 (4) |
C15 | 0.125 (5) | 0.046 (3) | 0.057 (3) | 0.020 (3) | −0.002 (3) | −0.003 (2) |
C16 | 0.077 (3) | 0.045 (2) | 0.048 (2) | 0.000 (2) | −0.007 (2) | −0.0096 (19) |
C17 | 0.052 (2) | 0.033 (2) | 0.042 (2) | 0.0013 (17) | 0.0189 (18) | 0.0030 (16) |
C18 | 0.072 (3) | 0.048 (2) | 0.051 (3) | 0.001 (2) | 0.026 (2) | −0.003 (2) |
C19 | 0.089 (4) | 0.065 (3) | 0.072 (3) | 0.010 (3) | 0.052 (3) | 0.000 (3) |
C20 | 0.059 (3) | 0.069 (3) | 0.086 (4) | 0.014 (2) | 0.045 (3) | 0.017 (3) |
C21 | 0.046 (2) | 0.054 (3) | 0.070 (3) | 0.0085 (19) | 0.019 (2) | 0.014 (2) |
C22 | 0.041 (2) | 0.036 (2) | 0.051 (2) | 0.0034 (16) | 0.0152 (17) | 0.0069 (17) |
C23 | 0.0375 (19) | 0.038 (2) | 0.045 (2) | −0.0031 (16) | 0.0017 (16) | 0.0092 (17) |
C24 | 0.047 (2) | 0.050 (2) | 0.0300 (18) | −0.0049 (18) | −0.0005 (16) | 0.0024 (16) |
C25 | 0.069 (3) | 0.058 (3) | 0.035 (2) | −0.017 (2) | 0.0005 (19) | 0.0093 (19) |
C26 | 0.075 (3) | 0.044 (2) | 0.041 (2) | −0.007 (2) | −0.007 (2) | 0.0138 (18) |
C27 | 0.044 (2) | 0.0310 (18) | 0.0362 (19) | −0.0025 (15) | 0.0058 (16) | −0.0013 (15) |
C28 | 0.063 (3) | 0.056 (3) | 0.066 (3) | −0.020 (2) | 0.013 (2) | 0.000 (2) |
C29 | 0.078 (4) | 0.078 (4) | 0.089 (4) | −0.044 (3) | 0.004 (3) | −0.014 (3) |
C30 | 0.144 (6) | 0.043 (3) | 0.094 (4) | −0.013 (4) | −0.013 (4) | −0.019 (3) |
C31 | 0.101 (4) | 0.060 (3) | 0.083 (4) | 0.023 (3) | 0.002 (3) | −0.028 (3) |
C32 | 0.059 (3) | 0.046 (2) | 0.061 (3) | 0.011 (2) | 0.000 (2) | −0.007 (2) |
Geometric parameters (Å, º) top
Co1—O2i | 1.883 (2) | C10—H10B | 0.9700 |
Co1—O2 | 1.883 (2) | C11—C12 | 1.509 (6) |
Co1—N3i | 1.926 (3) | C11—C16 | 1.512 (5) |
Co1—N3 | 1.926 (3) | C11—H11 | 0.9800 |
Co1—N4i | 2.007 (3) | C12—C13 | 1.515 (7) |
Co1—N4 | 2.007 (3) | C12—H12A | 0.9700 |
Co2—O1 | 1.886 (2) | C12—H12B | 0.9700 |
Co2—O1ii | 1.886 (2) | C13—C14 | 1.493 (9) |
Co2—N1 | 1.924 (3) | C13—H13A | 0.9700 |
Co2—N1ii | 1.924 (3) | C13—H13B | 0.9700 |
Co2—N2 | 2.010 (3) | C14—C15 | 1.501 (8) |
Co2—N2ii | 2.010 (3) | C14—H14A | 0.9700 |
Cl1—C2 | 1.739 (5) | C14—H14B | 0.9700 |
Cl2—C4 | 1.746 (4) | C15—C16 | 1.543 (6) |
Cl3—C18 | 1.738 (5) | C15—H15A | 0.9700 |
Cl4—C20 | 1.743 (5) | C15—H15B | 0.9700 |
Cl5—O5 | 1.357 (7) | C16—H16A | 0.9700 |
Cl5—O4 | 1.361 (7) | C16—H16B | 0.9700 |
Cl5—O4' | 1.363 (9) | C17—C18 | 1.416 (5) |
Cl5—O6' | 1.367 (9) | C17—C22 | 1.416 (6) |
Cl5—O3 | 1.377 (7) | C18—C19 | 1.370 (6) |
Cl5—O3' | 1.384 (8) | C19—C20 | 1.378 (8) |
Cl5—O6 | 1.388 (7) | C19—H19 | 0.9300 |
Cl5—O5' | 1.390 (8) | C20—C21 | 1.357 (7) |
O1—C1 | 1.304 (4) | C21—C22 | 1.406 (5) |
O2—C17 | 1.296 (4) | C21—H21 | 0.9300 |
N1—C7 | 1.274 (5) | C22—C23 | 1.429 (5) |
N1—C8 | 1.478 (5) | C23—H23 | 0.9300 |
N2—C10 | 1.479 (5) | C24—C25 | 1.523 (5) |
N2—C11 | 1.518 (5) | C24—H24A | 0.9700 |
N2—H2 | 0.90 (4) | C24—H24B | 0.9700 |
N3—C23 | 1.286 (5) | C25—C26 | 1.482 (6) |
N3—C24 | 1.472 (4) | C25—H25A | 0.9700 |
N4—C26 | 1.466 (5) | C25—H25B | 0.9700 |
N4—C27 | 1.517 (5) | C26—H26A | 0.9700 |
N4—H4 | 0.90 (4) | C26—H26B | 0.9700 |
C1—C2 | 1.404 (5) | C27—C32 | 1.500 (5) |
C1—C6 | 1.405 (5) | C27—C28 | 1.512 (5) |
C2—C3 | 1.379 (6) | C27—H27 | 0.9800 |
C3—C4 | 1.372 (7) | C28—C29 | 1.523 (7) |
C3—H3 | 0.9300 | C28—H28A | 0.9700 |
C4—C5 | 1.348 (6) | C28—H28B | 0.9700 |
C5—C6 | 1.403 (5) | C29—C30 | 1.509 (8) |
C5—H5 | 0.9300 | C29—H29A | 0.9700 |
C6—C7 | 1.447 (5) | C29—H29B | 0.9700 |
C7—H7 | 0.9300 | C30—C31 | 1.503 (9) |
C8—C9 | 1.523 (6) | C30—H30A | 0.9700 |
C8—H8A | 0.9700 | C30—H30B | 0.9700 |
C8—H8B | 0.9700 | C31—C32 | 1.524 (6) |
C9—C10 | 1.487 (6) | C31—H31A | 0.9700 |
C9—H9A | 0.9700 | C31—H31B | 0.9700 |
C9—H9B | 0.9700 | C32—H32A | 0.9700 |
C10—H10A | 0.9700 | C32—H32B | 0.9700 |
| | | |
O2i—Co1—O2 | 180.0 | C9—C10—H10B | 108.6 |
O2i—Co1—N3i | 91.26 (12) | H10A—C10—H10B | 107.6 |
O2—Co1—N3i | 88.74 (12) | C12—C11—C16 | 111.7 (4) |
O2i—Co1—N3 | 88.74 (12) | C12—C11—N2 | 114.3 (3) |
O2—Co1—N3 | 91.26 (12) | C16—C11—N2 | 110.4 (3) |
N3i—Co1—N3 | 180.0 | C12—C11—H11 | 106.7 |
O2i—Co1—N4i | 89.93 (12) | C16—C11—H11 | 106.7 |
O2—Co1—N4i | 90.07 (12) | N2—C11—H11 | 106.7 |
N3i—Co1—N4i | 88.58 (13) | C11—C12—C13 | 110.1 (4) |
N3—Co1—N4i | 91.42 (13) | C11—C12—H12A | 109.6 |
O2i—Co1—N4 | 90.07 (12) | C13—C12—H12A | 109.6 |
O2—Co1—N4 | 89.93 (12) | C11—C12—H12B | 109.6 |
N3i—Co1—N4 | 91.42 (13) | C13—C12—H12B | 109.6 |
N3—Co1—N4 | 88.58 (13) | H12A—C12—H12B | 108.2 |
N4i—Co1—N4 | 180.0 | C14—C13—C12 | 111.0 (5) |
O1—Co2—O1ii | 180.0 | C14—C13—H13A | 109.4 |
O1—Co2—N1 | 91.10 (12) | C12—C13—H13A | 109.4 |
O1ii—Co2—N1 | 88.90 (12) | C14—C13—H13B | 109.4 |
O1—Co2—N1ii | 88.90 (12) | C12—C13—H13B | 109.4 |
O1ii—Co2—N1ii | 91.10 (12) | H13A—C13—H13B | 108.0 |
N1—Co2—N1ii | 180.0 | C13—C14—C15 | 111.7 (5) |
O1—Co2—N2 | 89.69 (12) | C13—C14—H14A | 109.3 |
O1ii—Co2—N2 | 90.31 (12) | C15—C14—H14A | 109.3 |
N1—Co2—N2 | 89.27 (13) | C13—C14—H14B | 109.3 |
N1ii—Co2—N2 | 90.73 (13) | C15—C14—H14B | 109.3 |
O1—Co2—N2ii | 90.31 (12) | H14A—C14—H14B | 107.9 |
O1ii—Co2—N2ii | 89.69 (12) | C14—C15—C16 | 110.5 (4) |
N1—Co2—N2ii | 90.73 (13) | C14—C15—H15A | 109.5 |
N1ii—Co2—N2ii | 89.27 (13) | C16—C15—H15A | 109.5 |
N2—Co2—N2ii | 180.0 | C14—C15—H15B | 109.5 |
O5—Cl5—O4 | 114.2 (7) | C16—C15—H15B | 109.5 |
O5—Cl5—O4' | 59.1 (8) | H15A—C15—H15B | 108.1 |
O4—Cl5—O4' | 173.1 (9) | C11—C16—C15 | 109.1 (4) |
O5—Cl5—O6' | 141.1 (8) | C11—C16—H16A | 109.9 |
O4—Cl5—O6' | 75.8 (10) | C15—C16—H16A | 109.9 |
O4'—Cl5—O6' | 110.3 (8) | C11—C16—H16B | 109.9 |
O5—Cl5—O3 | 111.1 (6) | C15—C16—H16B | 109.9 |
O4—Cl5—O3 | 107.2 (7) | H16A—C16—H16B | 108.3 |
O4'—Cl5—O3 | 77.8 (8) | O2—C17—C18 | 119.9 (4) |
O5—Cl5—O3' | 104.7 (6) | O2—C17—C22 | 124.0 (3) |
O4—Cl5—O3' | 67.4 (7) | C18—C17—C22 | 116.1 (4) |
O4'—Cl5—O3' | 111.8 (7) | C19—C18—C17 | 122.0 (5) |
O6'—Cl5—O3' | 113.5 (8) | C19—C18—Cl3 | 120.3 (4) |
O3—Cl5—O3' | 142.1 (7) | C17—C18—Cl3 | 117.7 (3) |
O5—Cl5—O6 | 109.0 (5) | C18—C19—C20 | 120.2 (4) |
O4—Cl5—O6 | 109.2 (7) | C18—C19—H19 | 119.9 |
O4'—Cl5—O6 | 73.4 (8) | C20—C19—H19 | 119.9 |
O6'—Cl5—O6 | 101.7 (9) | C21—C20—C19 | 120.6 (4) |
O3—Cl5—O6 | 105.9 (7) | C21—C20—Cl4 | 120.3 (5) |
O3'—Cl5—O6 | 48.8 (6) | C19—C20—Cl4 | 119.1 (4) |
O5—Cl5—O5' | 53.1 (8) | C20—C21—C22 | 120.3 (5) |
O4—Cl5—O5' | 66.4 (9) | C20—C21—H21 | 119.8 |
O4'—Cl5—O5' | 107.9 (8) | C22—C21—H21 | 119.8 |
O6'—Cl5—O5' | 107.0 (8) | C21—C22—C17 | 120.7 (4) |
O3—Cl5—O5' | 105.2 (9) | C21—C22—C23 | 118.4 (4) |
O3'—Cl5—O5' | 106.0 (6) | C17—C22—C23 | 120.4 (3) |
O6—Cl5—O5' | 148.4 (9) | N3—C23—C22 | 125.9 (4) |
C1—O1—Co2 | 125.8 (2) | N3—C23—H23 | 117.0 |
C17—O2—Co1 | 126.7 (2) | C22—C23—H23 | 117.0 |
C7—N1—C8 | 117.6 (3) | N3—C24—C25 | 110.5 (3) |
C7—N1—Co2 | 124.8 (3) | N3—C24—H24A | 109.6 |
C8—N1—Co2 | 117.5 (2) | C25—C24—H24A | 109.6 |
C10—N2—C11 | 114.9 (3) | N3—C24—H24B | 109.6 |
C10—N2—Co2 | 115.1 (3) | C25—C24—H24B | 109.6 |
C11—N2—Co2 | 114.5 (2) | H24A—C24—H24B | 108.1 |
C10—N2—H2 | 103 (3) | C26—C25—C24 | 115.3 (3) |
C11—N2—H2 | 107 (3) | C26—C25—H25A | 108.4 |
Co2—N2—H2 | 101 (3) | C24—C25—H25A | 108.4 |
C23—N3—C24 | 117.5 (3) | C26—C25—H25B | 108.4 |
C23—N3—Co1 | 124.8 (3) | C24—C25—H25B | 108.4 |
C24—N3—Co1 | 117.5 (2) | H25A—C25—H25B | 107.5 |
C26—N4—C27 | 115.4 (3) | N4—C26—C25 | 116.4 (4) |
C26—N4—Co1 | 115.8 (2) | N4—C26—H26A | 108.2 |
C27—N4—Co1 | 115.9 (2) | C25—C26—H26A | 108.2 |
C26—N4—H4 | 99 (3) | N4—C26—H26B | 108.2 |
C27—N4—H4 | 105 (3) | C25—C26—H26B | 108.2 |
Co1—N4—H4 | 103 (3) | H26A—C26—H26B | 107.3 |
O1—C1—C2 | 119.8 (4) | C32—C27—C28 | 111.8 (4) |
O1—C1—C6 | 124.1 (3) | C32—C27—N4 | 114.1 (3) |
C2—C1—C6 | 116.1 (4) | C28—C27—N4 | 110.3 (3) |
C3—C2—C1 | 122.3 (4) | C32—C27—H27 | 106.7 |
C3—C2—Cl1 | 119.1 (3) | C28—C27—H27 | 106.7 |
C1—C2—Cl1 | 118.6 (3) | N4—C27—H27 | 106.7 |
C4—C3—C2 | 118.9 (4) | C27—C28—C29 | 110.1 (4) |
C4—C3—H3 | 120.5 | C27—C28—H28A | 109.6 |
C2—C3—H3 | 120.5 | C29—C28—H28A | 109.6 |
C5—C4—C3 | 121.8 (4) | C27—C28—H28B | 109.6 |
C5—C4—Cl2 | 120.1 (4) | C29—C28—H28B | 109.6 |
C3—C4—Cl2 | 118.1 (4) | H28A—C28—H28B | 108.2 |
C4—C5—C6 | 119.5 (4) | C30—C29—C28 | 111.6 (5) |
C4—C5—H5 | 120.2 | C30—C29—H29A | 109.3 |
C6—C5—H5 | 120.2 | C28—C29—H29A | 109.3 |
C5—C6—C1 | 121.1 (4) | C30—C29—H29B | 109.3 |
C5—C6—C7 | 118.3 (4) | C28—C29—H29B | 109.3 |
C1—C6—C7 | 120.1 (3) | H29A—C29—H29B | 108.0 |
N1—C7—C6 | 125.7 (3) | C31—C30—C29 | 111.6 (4) |
N1—C7—H7 | 117.2 | C31—C30—H30A | 109.3 |
C6—C7—H7 | 117.2 | C29—C30—H30A | 109.3 |
N1—C8—C9 | 110.3 (3) | C31—C30—H30B | 109.3 |
N1—C8—H8A | 109.6 | C29—C30—H30B | 109.3 |
C9—C8—H8A | 109.6 | H30A—C30—H30B | 108.0 |
N1—C8—H8B | 109.6 | C30—C31—C32 | 111.2 (5) |
C9—C8—H8B | 109.6 | C30—C31—H31A | 109.4 |
H8A—C8—H8B | 108.1 | C32—C31—H31A | 109.4 |
C10—C9—C8 | 115.3 (4) | C30—C31—H31B | 109.4 |
C10—C9—H9A | 108.5 | C32—C31—H31B | 109.4 |
C8—C9—H9A | 108.5 | H31A—C31—H31B | 108.0 |
C10—C9—H9B | 108.5 | C27—C32—C31 | 109.5 (4) |
C8—C9—H9B | 108.5 | C27—C32—H32A | 109.8 |
H9A—C9—H9B | 107.5 | C31—C32—H32A | 109.8 |
N2—C10—C9 | 114.6 (4) | C27—C32—H32B | 109.8 |
N2—C10—H10A | 108.6 | C31—C32—H32B | 109.8 |
C9—C10—H10A | 108.6 | H32A—C32—H32B | 108.2 |
N2—C10—H10B | 108.6 | | |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O4iii | 0.90 (4) | 2.55 (4) | 3.223 (8) | 132 (4) |
Symmetry code: (iii) −x, y+1/2, −z+1/2. |
Experimental details
Crystal data |
Chemical formula | [Co(C16H21Cl2N2O)2]·ClO4 |
Mr | 814.88 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 16.136 (2), 12.752 (2), 17.771 (2) |
β (°) | 99.486 (1) |
V (Å3) | 3606.7 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.90 |
Crystal size (mm) | 0.35 × 0.17 × 0.13 |
|
Data collection |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.745, 0.893 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 30380, 8227, 6373 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.650 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.073, 0.160, 1.15 |
No. of reflections | 8227 |
No. of parameters | 479 |
No. of restraints | 44 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.56, −0.38 |
Selected geometric parameters (Å, º) topCo1—O2 | 1.883 (2) | Co2—O1 | 1.886 (2) |
Co1—N3 | 1.926 (3) | Co2—N1 | 1.924 (3) |
Co1—N4 | 2.007 (3) | Co2—N2 | 2.010 (3) |
| | | |
O2i—Co1—O2 | 180.0 | O1—Co2—O1ii | 180.0 |
O2i—Co1—N3 | 88.74 (12) | O1—Co2—N1 | 91.10 (12) |
O2—Co1—N3 | 91.26 (12) | O1ii—Co2—N1 | 88.90 (12) |
N3i—Co1—N3 | 180.0 | N1—Co2—N1ii | 180.0 |
O2i—Co1—N4 | 90.07 (12) | O1—Co2—N2 | 89.69 (12) |
O2—Co1—N4 | 89.93 (12) | O1ii—Co2—N2 | 90.31 (12) |
N3i—Co1—N4 | 91.42 (13) | N1—Co2—N2 | 89.27 (13) |
N3—Co1—N4 | 88.58 (13) | N1ii—Co2—N2 | 90.73 (13) |
N4i—Co1—N4 | 180.0 | N2—Co2—N2ii | 180.0 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O4iii | 0.90 (4) | 2.55 (4) | 3.223 (8) | 132 (4) |
Symmetry code: (iii) −x, y+1/2, −z+1/2. |
Schiff base complexes are very important in coordination chemistry because of their easy preparation, interesting structures and excellent properties (Chang et al., 1998; Chaturvedl, 1977; Archer & Wang, 1990; Costamagna et al., 1992; Bhatia et al., 1981). In order to investigate the crystal structures of such complexes, a new cobalt(III) complex, (I), is reported here.
Compound (I) is a perchlorate salt of discrete mononuclear cobalt(III) complex cations (Fig. 1). The structure is similar to that recently reported for the cobalt(III) complex containing the 3-[(3-cyclohexylaminopropylimino)methyl]naphthalen-2-olate ligand (Li et al., 2004). The are two independent half-molecules of the cation in the asymmetric unit. The symmetry of both cations is Ci. Both CoIII atoms are in a slightly distorted octahedral geometry provided by two O and four N atoms from two Schiff bases. The bond lengths and angles involving the Co atoms are the same (within experimental error) in each molecule (Table 1) and are comparable to those of the complex previously cited. As expected, the cyclohexyl groups adopt a chair conformations to minimize the steric effects. The unique ClO4− anion is disordered over two sites with occupancies 0.581 (2):0.419 (2). The crystal packing is shown in Fig. 2.