[N,N'-Bis(1-benzoyl­ethyl­idene)propyl­ene­diiminato(2-)]dipyrrolidinecobalt(III) perchlorate

In the title compound, [Co(C₂₃H₂₄N₂O₂)(C₄H₉N)₂]ClO₄, the N,N'-bis­(1-benzoyl­ethyl­idene)propyl­enediimine dianion, (BA)₂pn, coordinates the Co^III ion in four equatorial positions and the two amine (pyrrolidine, prldn) mol­ecules occupy the two axial positions. The Co^III ion has a slightly distorted octa­hedral coordination geometry. The N atoms of the pyrrolidine axial ligands are involved in hydrogen bonds with the O atoms of the perchlorate anions, forming chains along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 183 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.050
• wR factor = 0.120
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.119
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.18 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.13 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C13
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         Cl

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 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
   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

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S1. Comment

Quadridentate Schiff base cobalt complexes have been extensively used to mimic the cobalamine (B₁₂) coenzyme (Hirota et al., 1998), as dioxygen carriers and oxygen activators (Yamada, 1999; Henson et al., 1999), and in enantioselective reduction (Nagata et al., 1995). Co(III) Schiff base complexes with two amines in the axial positions have also been used as antimicrobial agents (Böttcher et al., 1997). More recently the interest in the influence of steric and electronic factors of both the equatorial chelating Schiff base ligand and the axial amines on the stability and reaction kinetics of these complexes have been renewed (Dreos et al., 2003; Amirnasr et al., 2005). In continuation of our work in this field, herein we report the X-ray structure of trans-[Co((BA)₂pn)(prldn)₂]ClO₄, (I).

As shown in Fig. 1, the structure exhibits a distorted octahedral environment around cobalt, with the (BA)₂pn ligand occupying the four equatorial positions. The Co—O1 [1.903 (2)] and Co—O2 [1.897 (2) Å] bonds of the (BA)₂pn (Table 1) are nearly the same and are in agreement with those reported for trans-[Co^III((BA)₂en)(ta)₂]PF₆, (II), [1.9004 (9) Å] (Amirnasr et al., 2005). The Co—N1 [1.937 (3)] and Co—N2 [1.992 (2) Å] bonds of the (BA)₂pn, however, are considerably longer than those of the corresponding ones [1.901 (1) Å] in (II) (Amirnasr et al., 2005) implying the existence of a higher steric hindrance in the N(CH₂)₃N chelate ring relative to N(CH₂)₂N. The axial Co—N3 [2.006 (3)] and Co—N4 [2.006 (3) Å] bonds are in agreement with those reported for trans-[Co^III(salophen)(prldn)₂]ClO₄ [2.006 (2) and 2.004 (2) Å] (Amirnasr et al., 2001).

The diagonal angles of 172.08 (10)° and 172.17 (10)° are indicative of a slight tetrahedral distortion of the basal coordination of Co(III), which in the case of perfect planarity have values of 180°. This distortion is also reflected by the selected torsion angles of the coordinating ligand (Table 1) and the angle [2.90 (11)°] between the best least-square planes of (Co/O1/C1—C3/N1) and (Co/N2/C7—C9/O2).

The N atoms of both pyrrolidine axial ligands are involved in the H bonds with the O atoms of the perchlorate anions forming chains along the a axis (Table 2, Fig. 2). This behavior has also been evidenced in the IR spectrum of the complex. The fairly broad band of medium intesity appearing at 1278 cm⁻¹, which corresponds to the intramolecular hydrogen bonding in the free ligand (Yamazaki & Hohokabe, 1971), is absent in the complex. The bands corresponding to the axial amine N—H stretching vibrations appear in the range of (3200–3300) cm⁻¹. These bands, as expected, are shifted to lower frequencies by 150 cm⁻¹ relative to the uncoordinated amine.

S2. Experimental

Equimolar (0.5 mmol) quantities of cobalt(II) acetate tetrahydrate and the ligand H₂(BA)₂pn [prepared according to the method of McCarthy et al. (1955)] were dissolved in methanol and pyrrolidine (1.5 mmol) was added to the solution and air was bubbled slowly through the reaction mixture for 3 h. Solid NaClO₄ (0.5 mmol) was then added to the resulting clear red solution and stirred for 5 min. The solution was filtered off and the filtrate was left undisturbed to give dark red-brown crystals of the complex (yield 0.250 g, 76%, m.p. 443 K) suitable for X-ray crystallography.

S3. Refinement

The structure was first solved using data from a Siemens SMART CCD system at room temperature (unit cell: a=9.4240 (3), b=12.0882 (4), c=29.4795 (8) Å, β=98.741°, space group: P2₁/n) but failed due to dynamic disorders of the perchlorate, phenyl rings and the propylene moiety reflected in high thermal parameters of the respective O/C atoms, and difficulties with modeling the disorder. Cooling at and below 173 K results in cracking of crystals. By careful examination in the range of 173 to 223 K, a more starisfactory result was obtained at 183 K.

H atoms were positioned geometrically [0.93 (NH), 0.95 (CH), 0.99 (CH₂) and 0.98 Å (CH₃)] and constrained to ride on their parent atoms with U_iso(H) = 1.2 (1.5 methyl) U_eq(C/N).

Computing details

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELX97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecular structure of the title compound, (I), with displacement ellipsoids drawn at 40% probability level. H atoms are omitted for clarity.
	Fig. 2. The extended chain structure of (I). The dashed lines denote hydrogen bonds.

[N,N'-Bis(1-benzoylethylidene)propylenediiminato(2-)]dipyrrolidinecobalt(III) perchlorate

Crystal data

[Co(C23H24N2O2)(C4H9N)2]ClO4	F(000) = 1392
Mr = 661.07	Dx = 1.398 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 7739 reflections
a = 9.323 (2) Å	θ = 1–25°
b = 13.355 (1) Å	µ = 0.68 mm^−1
c = 25.701 (1) Å	T = 183 K
β = 101.030 (2)°	Rectangular prism, dark red-brown
V = 3140.9 (7) Å^3	0.34 × 0.08 × 0.04 mm
Z = 4

Data collection

Nonius KappaCCD area-detector diffractometer	5948 independent reflections
Radiation source: fine-focus sealed tube	3975 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.119
ω and ϕ scans	θmax = 25.8°, θmin = 1.7°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −11→11
Tmin = 0.855, Tmax = 0.977	k = −16→16
30114 measured reflections	l = −31→31

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0496P)^2 + 2.0135P] where P = (Fo^2 + 2Fc^2)/3
5948 reflections	(Δ/σ)max < 0.001
390 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.56 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Co	0.48037 (4)	0.75504 (3)	0.136068 (15)	0.02246 (13)
Cl	−0.00675 (9)	0.58229 (6)	0.18551 (3)	0.0347 (2)
O1	0.4935 (2)	0.89679 (15)	0.13568 (8)	0.0266 (5)
N1	0.6136 (3)	0.74653 (18)	0.20641 (9)	0.0240 (6)
C1	0.5994 (3)	0.9509 (2)	0.16092 (12)	0.0248 (7)
O2	0.3678 (2)	0.77904 (16)	0.06725 (8)	0.0265 (5)
N2	0.4407 (3)	0.61269 (19)	0.13012 (10)	0.0260 (6)
C2	0.7073 (3)	0.9147 (2)	0.20072 (12)	0.0276 (7)
H2	0.7882	0.9571	0.2134	0.033*
C3	0.7060 (3)	0.8190 (2)	0.22405 (12)	0.0248 (7)
N3	0.6524 (3)	0.7398 (2)	0.10027 (10)	0.0294 (6)
H3	0.7329	0.7282	0.1271	0.035*
N4	0.3028 (3)	0.77545 (19)	0.16824 (10)	0.0252 (6)
H4	0.2561	0.7136	0.1665	0.030*
C4	0.6197 (4)	0.6606 (2)	0.24375 (12)	0.0299 (8)
H4A	0.5931	0.6851	0.2770	0.036*
H4B	0.7218	0.6362	0.2525	0.036*
C5	0.5218 (4)	0.5734 (2)	0.22358 (13)	0.0308 (8)
H5A	0.4190	0.5910	0.2242	0.037*
H5B	0.5487	0.5147	0.2470	0.037*
C6	0.5368 (4)	0.5472 (2)	0.16750 (13)	0.0331 (8)
H6A	0.6395	0.5562	0.1634	0.040*
H6B	0.5094	0.4763	0.1600	0.040*
C7	0.3248 (3)	0.5738 (2)	0.09949 (12)	0.0288 (7)
C8	0.2317 (4)	0.6295 (2)	0.05978 (12)	0.0304 (8)
H8	0.1422	0.5993	0.0433	0.036*
C9	0.2607 (3)	0.7234 (2)	0.04339 (12)	0.0259 (7)
C10	0.2830 (4)	0.4649 (2)	0.10411 (15)	0.0408 (9)
H10A	0.3519	0.4222	0.0899	0.061*
H10B	0.1840	0.4539	0.0839	0.061*
H10C	0.2862	0.4484	0.1415	0.061*
O11	0.1488 (2)	0.58179 (18)	0.18954 (10)	0.0424 (6)
C11	0.5961 (3)	1.0585 (2)	0.14427 (12)	0.0274 (7)
O12	−0.0631 (3)	0.67948 (18)	0.16650 (11)	0.0504 (7)
C12	0.4726 (4)	1.0956 (3)	0.11123 (17)	0.0586 (13)
H12	0.3913	1.0528	0.0998	0.070*
O13	−0.0728 (3)	0.5057 (2)	0.15042 (12)	0.0691 (9)
C13	0.4663 (5)	1.1945 (3)	0.0946 (2)	0.0787 (17)
H13	0.3797	1.2196	0.0729	0.094*
O14	−0.0379 (3)	0.5660 (2)	0.23736 (11)	0.0594 (8)
C14	0.5850 (5)	1.2564 (3)	0.10946 (16)	0.0505 (10)
H14	0.5825	1.3232	0.0966	0.061*
C15	0.7058 (4)	1.2214 (3)	0.14271 (14)	0.0381 (9)
H15	0.7870	1.2644	0.1538	0.046*
C16	0.7110 (4)	1.1232 (2)	0.16041 (13)	0.0345 (8)
H16	0.7954	1.1000	0.1841	0.041*
C20	0.8163 (4)	0.8064 (3)	0.27527 (13)	0.0335 (8)
H20A	0.7647	0.7976	0.3048	0.050*
H20B	0.8785	0.8660	0.2815	0.050*
H20C	0.8770	0.7474	0.2726	0.050*
C21	0.1659 (3)	0.7706 (2)	−0.00354 (12)	0.0273 (7)
C22	0.1646 (4)	0.8740 (3)	−0.00972 (13)	0.0356 (8)
H22	0.2286	0.9142	0.0150	0.043*
C23	0.0709 (4)	0.9192 (3)	−0.05156 (14)	0.0440 (9)
H23	0.0694	0.9900	−0.0549	0.053*
C24	−0.0194 (4)	0.8619 (3)	−0.08815 (15)	0.0482 (10)
H24	−0.0839	0.8931	−0.1166	0.058*
C25	−0.0169 (4)	0.7592 (3)	−0.08377 (14)	0.0457 (10)
H25	−0.0791	0.7198	−0.1094	0.055*
C26	0.0755 (4)	0.7133 (3)	−0.04222 (13)	0.0370 (9)
H26	0.0778	0.6423	−0.0398	0.044*
C31	0.6497 (4)	0.6564 (3)	0.06169 (14)	0.0392 (9)
H31A	0.5552	0.6549	0.0364	0.047*
H31B	0.6641	0.5912	0.0803	0.047*
C32	0.7755 (4)	0.6777 (3)	0.03277 (15)	0.0469 (10)
H32A	0.8637	0.6392	0.0489	0.056*
H32B	0.7479	0.6592	−0.0051	0.056*
C33	0.8041 (4)	0.7889 (3)	0.03864 (15)	0.0466 (10)
H33A	0.7914	0.8216	0.0035	0.056*
H33B	0.9046	0.8019	0.0582	0.056*
C34	0.6912 (4)	0.8279 (3)	0.06983 (14)	0.0392 (9)
H34A	0.7332	0.8823	0.0942	0.047*
H34B	0.6038	0.8537	0.0455	0.047*
C41	0.1907 (3)	0.8483 (3)	0.13957 (13)	0.0320 (8)
H41A	0.1096	0.8117	0.1169	0.038*
H41B	0.2360	0.8936	0.1168	0.038*
C42	0.1337 (4)	0.9082 (3)	0.18193 (14)	0.0456 (10)
H42A	0.1746	0.9768	0.1846	0.055*
H42B	0.0257	0.9126	0.1735	0.055*
C43	0.1843 (4)	0.8510 (3)	0.23333 (13)	0.0348 (8)
H43A	0.1988	0.8964	0.2643	0.042*
H43B	0.1135	0.7981	0.2381	0.042*
C44	0.3274 (4)	0.8064 (2)	0.22521 (12)	0.0290 (8)
H44A	0.4068	0.8566	0.2329	0.035*
H44B	0.3541	0.7478	0.2487	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co	0.0201 (2)	0.0259 (2)	0.0205 (2)	−0.00056 (19)	0.00176 (16)	−0.00040 (19)
Cl	0.0246 (4)	0.0337 (5)	0.0442 (5)	0.0004 (4)	0.0022 (4)	0.0067 (4)
O1	0.0256 (12)	0.0255 (11)	0.0274 (12)	−0.0015 (10)	0.0022 (9)	0.0024 (10)
N1	0.0224 (14)	0.0275 (14)	0.0217 (13)	0.0030 (12)	0.0033 (10)	0.0014 (12)
C1	0.0219 (17)	0.0288 (17)	0.0239 (16)	−0.0035 (14)	0.0054 (13)	−0.0035 (14)
O2	0.0216 (12)	0.0330 (12)	0.0227 (11)	−0.0043 (10)	−0.0013 (9)	0.0010 (9)
N2	0.0245 (15)	0.0267 (14)	0.0264 (14)	0.0022 (12)	0.0034 (12)	−0.0021 (12)
C2	0.0219 (17)	0.0298 (17)	0.0294 (17)	−0.0018 (14)	0.0006 (13)	−0.0008 (14)
C3	0.0218 (17)	0.0296 (17)	0.0230 (16)	0.0035 (14)	0.0039 (13)	−0.0042 (14)
N3	0.0230 (14)	0.0432 (17)	0.0204 (13)	0.0017 (13)	0.0003 (11)	−0.0032 (13)
N4	0.0236 (14)	0.0246 (14)	0.0268 (14)	−0.0010 (11)	0.0032 (11)	−0.0017 (11)
C4	0.0298 (19)	0.0321 (18)	0.0262 (17)	0.0018 (15)	0.0014 (14)	0.0064 (14)
C5	0.0319 (19)	0.0271 (18)	0.0328 (18)	0.0027 (15)	0.0042 (15)	0.0109 (15)
C6	0.0304 (19)	0.0296 (18)	0.0361 (19)	0.0069 (15)	−0.0015 (15)	0.0015 (15)
C7	0.0309 (19)	0.0297 (18)	0.0265 (17)	−0.0013 (15)	0.0075 (15)	−0.0020 (14)
C8	0.0262 (18)	0.0309 (18)	0.0311 (18)	−0.0053 (15)	−0.0019 (14)	−0.0016 (15)
C9	0.0192 (17)	0.039 (2)	0.0204 (16)	−0.0001 (14)	0.0064 (13)	−0.0060 (14)
C10	0.048 (2)	0.0289 (19)	0.045 (2)	−0.0021 (17)	0.0052 (18)	−0.0047 (16)
O11	0.0215 (12)	0.0443 (15)	0.0624 (17)	0.0017 (11)	0.0102 (11)	0.0094 (13)
C11	0.0307 (19)	0.0276 (17)	0.0231 (16)	−0.0001 (14)	0.0031 (14)	−0.0032 (14)
O12	0.0380 (15)	0.0394 (15)	0.0681 (18)	0.0099 (12)	−0.0045 (13)	0.0172 (13)
C12	0.049 (3)	0.039 (2)	0.073 (3)	−0.008 (2)	−0.025 (2)	0.008 (2)
O13	0.0608 (19)	0.0541 (18)	0.081 (2)	−0.0090 (15)	−0.0160 (17)	−0.0170 (16)
C13	0.072 (3)	0.041 (3)	0.102 (4)	−0.003 (2)	−0.036 (3)	0.025 (3)
O14	0.0545 (18)	0.071 (2)	0.0595 (18)	0.0016 (15)	0.0283 (14)	0.0197 (15)
C14	0.062 (3)	0.028 (2)	0.058 (3)	−0.001 (2)	0.003 (2)	0.0070 (19)
C15	0.046 (2)	0.0321 (19)	0.037 (2)	−0.0114 (17)	0.0116 (18)	−0.0013 (16)
C16	0.033 (2)	0.0328 (19)	0.0350 (19)	−0.0049 (16)	0.0013 (16)	0.0006 (16)
C20	0.033 (2)	0.036 (2)	0.0280 (18)	−0.0006 (16)	−0.0029 (15)	−0.0015 (15)
C21	0.0224 (17)	0.0345 (19)	0.0250 (17)	−0.0028 (14)	0.0047 (13)	0.0022 (14)
C22	0.033 (2)	0.042 (2)	0.0293 (19)	−0.0026 (17)	0.0008 (15)	−0.0019 (16)
C23	0.047 (2)	0.044 (2)	0.039 (2)	0.0034 (19)	0.0032 (18)	0.0093 (18)
C24	0.038 (2)	0.067 (3)	0.034 (2)	−0.003 (2)	−0.0056 (17)	0.018 (2)
C25	0.042 (2)	0.061 (3)	0.0282 (19)	−0.018 (2)	−0.0075 (16)	0.0101 (19)
C26	0.034 (2)	0.046 (2)	0.0297 (19)	−0.0106 (17)	0.0036 (16)	0.0009 (16)
C31	0.038 (2)	0.045 (2)	0.037 (2)	0.0035 (18)	0.0109 (16)	−0.0065 (17)
C32	0.043 (2)	0.066 (3)	0.035 (2)	0.014 (2)	0.0165 (18)	−0.0042 (19)
C33	0.033 (2)	0.076 (3)	0.032 (2)	−0.009 (2)	0.0107 (16)	−0.0080 (19)
C34	0.040 (2)	0.049 (2)	0.0333 (19)	−0.0132 (18)	0.0176 (16)	−0.0069 (17)
C41	0.0237 (18)	0.0382 (19)	0.0334 (18)	0.0057 (15)	0.0036 (14)	0.0027 (15)
C42	0.049 (2)	0.052 (2)	0.037 (2)	0.025 (2)	0.0107 (17)	0.0025 (18)
C43	0.034 (2)	0.038 (2)	0.0343 (19)	0.0075 (16)	0.0126 (16)	−0.0015 (16)
C44	0.0321 (19)	0.0315 (18)	0.0237 (17)	0.0017 (15)	0.0064 (14)	0.0002 (14)

Geometric parameters (Å, º)

Co—O1	1.897 (2)	C13—H13	0.9500
Co—O2	1.903 (2)	C14—C15	1.360 (5)
Co—N2	1.937 (3)	C14—H14	0.9500
Co—N1	1.991 (2)	C15—C16	1.386 (5)
Co—N4	2.006 (3)	C15—H15	0.9500
Co—N3	2.007 (3)	C16—H16	0.9500
Cl—O13	1.423 (3)	C21—C22	1.391 (5)
Cl—O11	1.434 (2)	C21—C26	1.401 (5)
Cl—O14	1.434 (3)	C22—C23	1.387 (5)
Cl—O12	1.450 (2)	C22—H22	0.9500
O1—C1	1.293 (3)	C23—C24	1.370 (5)
N1—C3	1.317 (4)	C23—H23	0.9500
N1—C4	1.490 (4)	C24—C25	1.375 (5)
C1—C2	1.378 (4)	C24—H24	0.9500
C1—C11	1.498 (4)	C25—C26	1.381 (5)
O2—C9	1.300 (4)	C25—H25	0.9500
N2—C7	1.316 (4)	C26—H26	0.9500
N2—C6	1.470 (4)	C31—C32	1.531 (5)
C2—C3	1.413 (4)	C31—H31A	0.9900
C2—H2	0.9500	C31—H31B	0.9900
C3—C20	1.517 (4)	C32—C33	1.512 (5)
N3—C31	1.488 (4)	C32—H32A	0.9900
N3—C34	1.495 (4)	C32—H32B	0.9900
N3—H3	0.9300	C33—C34	1.531 (5)
N4—C44	1.496 (4)	C33—H33A	0.9900
N4—C41	1.512 (4)	C33—H33B	0.9900
N4—H4	0.9300	C34—H34A	0.9900
C4—C5	1.509 (4)	C34—H34B	0.9900
C4—H4A	0.9900	C41—C42	1.526 (5)
C4—H4B	0.9900	C41—H41A	0.9900
C5—C6	1.516 (5)	C41—H41B	0.9900
C5—H5A	0.9900	C42—C43	1.521 (5)
C5—H5B	0.9900	C42—H42A	0.9900
C6—H6A	0.9900	C42—H42B	0.9900
C6—H6B	0.9900	C43—C44	1.512 (5)
C7—C8	1.417 (4)	C43—H43A	0.9900
C7—C10	1.516 (4)	C43—H43B	0.9900
C8—C9	1.366 (4)	C44—H44A	0.9900
C8—H8	0.9500	C44—H44B	0.9900
C9—C21	1.492 (4)	C10—H10A	0.9800
C11—C16	1.377 (4)	C10—H10B	0.9800
C11—C12	1.385 (5)	C10—H10C	0.9800
C12—C13	1.386 (5)	C20—H20A	0.9800
C12—H12	0.9500	C20—H20B	0.9800
C13—C14	1.375 (6)	C20—H20C	0.9800
O1—Co—O2	81.48 (9)	C15—C14—H14	120.2
O1—Co—N2	172.06 (10)	C13—C14—H14	120.2
O2—Co—N2	91.66 (10)	C14—C15—C16	120.3 (3)
O1—Co—N1	91.83 (9)	C14—C15—H15	119.9
O2—Co—N1	172.16 (10)	C16—C15—H15	119.9
N2—Co—N1	95.28 (10)	C11—C16—C15	121.2 (3)
O1—Co—N4	85.76 (10)	C11—C16—H16	119.4
O2—Co—N4	90.48 (10)	C15—C16—H16	119.4
N2—Co—N4	90.33 (11)	C22—C21—C26	118.1 (3)
N1—Co—N4	93.11 (10)	C22—C21—C9	120.2 (3)
O1—Co—N3	92.32 (10)	C26—C21—C9	121.7 (3)
O2—Co—N3	86.44 (10)	C23—C22—C21	120.7 (3)
N2—Co—N3	91.23 (11)	C23—C22—H22	119.6
N1—Co—N3	89.77 (10)	C21—C22—H22	119.6
N4—Co—N3	176.59 (10)	C24—C23—C22	120.2 (4)
O13—Cl—O11	110.6 (2)	C24—C23—H23	119.9
O13—Cl—O14	109.8 (2)	C22—C23—H23	119.9
O11—Cl—O14	108.3 (2)	C23—C24—C25	120.1 (3)
O13—Cl—O12	110.2 (2)	C23—C24—H24	119.9
O11—Cl—O12	108.9 (2)	C25—C24—H24	119.9
O14—Cl—O12	108.9 (2)	C24—C25—C26	120.3 (3)
C1—O1—Co	126.8 (2)	C24—C25—H25	119.8
C3—N1—C4	113.7 (2)	C26—C25—H25	119.8
C3—N1—Co	121.6 (2)	C25—C26—C21	120.5 (3)
C4—N1—Co	124.7 (2)	C25—C26—H26	119.8
O1—C1—C2	123.7 (3)	C21—C26—H26	119.8
O1—C1—C11	114.9 (3)	N3—C31—C32	105.5 (3)
C2—C1—C11	121.4 (3)	N3—C31—H31A	110.6
C9—O2—Co	125.4 (2)	C32—C31—H31A	110.6
C7—N2—C6	119.0 (3)	N3—C31—H31B	110.6
C7—N2—Co	123.8 (2)	C32—C31—H31B	110.6
C6—N2—Co	116.7 (2)	H31A—C31—H31B	108.8
C1—C2—C3	124.7 (3)	C33—C32—C31	105.7 (3)
C1—C2—H2	117.7	C33—C32—H32A	110.6
C3—C2—H2	117.7	C31—C32—H32A	110.6
N1—C3—C2	125.2 (3)	C33—C32—H32B	110.6
N1—C3—C20	120.5 (3)	C31—C32—H32B	110.6
C2—C3—C20	114.2 (3)	H32A—C32—H32B	108.7
C31—N3—C34	102.4 (3)	C32—C33—C34	105.1 (3)
C31—N3—Co	117.9 (2)	C32—C33—H33A	110.7
C34—N3—Co	117.1 (2)	C34—C33—H33A	110.7
C31—N3—H3	106.2	C32—C33—H33B	110.7
C34—N3—H3	106.2	C34—C33—H33B	110.7
Co—N3—H3	106.2	H33A—C33—H33B	108.8
C44—N4—C41	105.2 (2)	N3—C34—C33	105.4 (3)
C44—N4—Co	117.2 (2)	N3—C34—H34A	110.7
C41—N4—Co	115.7 (2)	C33—C34—H34A	110.7
C44—N4—H4	106.0	N3—C34—H34B	110.7
C41—N4—H4	106.0	C33—C34—H34B	110.7
Co—N4—H4	106.0	H34A—C34—H34B	108.8
N1—C4—C5	115.3 (2)	N4—C41—C42	107.0 (3)
N1—C4—H4A	108.5	N4—C41—H41A	110.3
C5—C4—H4A	108.5	C42—C41—H41A	110.3
N1—C4—H4B	108.5	N4—C41—H41B	110.3
C5—C4—H4B	108.5	C42—C41—H41B	110.3
H4A—C4—H4B	107.5	H41A—C41—H41B	108.6
C4—C5—C6	110.2 (3)	C43—C42—C41	105.3 (3)
C4—C5—H5A	109.6	C43—C42—H42A	110.7
C6—C5—H5A	109.6	C41—C42—H42A	110.7
C4—C5—H5B	109.6	C43—C42—H42B	110.7
C6—C5—H5B	109.6	C41—C42—H42B	110.7
H5A—C5—H5B	108.1	H42A—C42—H42B	108.8
N2—C6—C5	109.2 (3)	C44—C43—C42	102.3 (3)
N2—C6—H6A	109.8	C44—C43—H43A	111.3
C5—C6—H6A	109.8	C42—C43—H43A	111.3
N2—C6—H6B	109.8	C44—C43—H43B	111.3
C5—C6—H6B	109.8	C42—C43—H43B	111.3
H6A—C6—H6B	108.3	H43A—C43—H43B	109.2
N2—C7—C8	122.9 (3)	N4—C44—C43	105.6 (3)
N2—C7—C10	121.7 (3)	N4—C44—H44A	110.6
C8—C7—C10	115.4 (3)	C43—C44—H44A	110.6
C9—C8—C7	125.0 (3)	N4—C44—H44B	110.6
C9—C8—H8	117.5	C43—C44—H44B	110.6
C7—C8—H8	117.5	H44A—C44—H44B	108.7
O2—C9—C8	124.0 (3)	C7—C10—H10A	109.5
O2—C9—C21	115.0 (3)	C7—C10—H10B	109.5
C8—C9—C21	121.0 (3)	H10A—C10—H10B	109.5
C16—C11—C12	117.9 (3)	C7—C10—H10C	109.5
C16—C11—C1	122.9 (3)	H10A—C10—H10C	109.5
C12—C11—C1	119.2 (3)	H10B—C10—H10C	109.5
C11—C12—C13	120.7 (4)	C3—C20—H20A	109.5
C11—C12—H12	119.6	C3—C20—H20B	109.5
C13—C12—H12	119.6	H20A—C20—H20B	109.5
C14—C13—C12	120.2 (4)	C3—C20—H20C	109.5
C14—C13—H13	119.9	H20A—C20—H20C	109.5
C12—C13—H13	119.9	H20B—C20—H20C	109.5
C15—C14—C13	119.6 (4)
N1—C3—C2—C1	10.0 (5)	N1—C4—C5—C6	46.6 (4)
O1—C1—C2—C3	−9.1 (5)	N2—C6—C5—C4	−83.8 (3)
N2—C7—C8—C9	9.8 (5)	O1—C1—C11—C16	−169.2 (3)
O2—C9—C8—C7	−10.1 (5)	O2—C8—C21—C26	163.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O12^i	0.93	2.08	2.975 (3)	161
N4—H4···O11	0.93	2.16	3.058 (3)	161
C4—H4B···O14^i	0.99	2.53	3.466 (4)	158
C5—H5A···O11	0.99	2.51	3.422 (4)	153

Symmetry code: (i) x+1, y, z.