Clemizoledichlorocobalt(II)

The structure of di­chloro­[1-(p-chloro­benzyl)-2-(1-pyrrol­idinyl­methyl-N)-1,3-benz­imidazole-N³]­cobalt(II), [Co­Cl₂(C₁₉­H₂₀ClN₃)], contains a mol­ecule of clemizole bound in a bidentate manner to cobalt through its imidazole and pyrrolidinyl N atoms, with significantly different Co-N distances of 1.976 (5) and 2.126 (5) Å, respectively. The geometry around cobalt is distorted tetrahedral, with significantly different Co-Cl distances of 2.217 (2) and 2.233 (2) Å, and the pyrrolidinyl ring is disordered.

S1. Comment

The crystal structures of clemizole hydrochloride (Parvez, 1996), clemizoledichlorozinc(II) (Parvez & Sabir, 1996a), clemizole as a free base (Parvez & Sabir, 1996b), clemizole tetrachlorocuprate(II) and clemizole tetrachlorocobaltate(II) (Parvez & Sabir, 1997) have been reported from our laboratory. This H₁ antihistamine has now been incorporated into a cobalt complex to investigate further the effects such complex formation may have on the conformation of the clemizole moiety. In this paper, we report the structure of clemizoledichlorocobalt(II), (I).

In (I) (Fig. 1), the clemizole is coordinated in a bidentate manner to cobalt via pyrrolidinyl and imidazole N atoms with significantly different Co—N distances of 1.976 (5) and 2.125 (5) Å, respectively. The Co atom is also bound to two Cl atoms with Co—Cl distances of 2.233 (2) and 2.217 (2) Å. The geometry around cobalt is distorted tetrahedral. Similar distances and geometry have been reported for a number of closely related cobalt complexes, e.g. dichlorobis(2-methoxypyridine)cobalt(II) (Allan et al., 1981), bis(1,3-benzothiazole)dichlorocobalt(II) (Oughtred et al., 1982), dichlorobis[2-(4-thiazolyl)-1H-benzimidazole-N,N']cobalt(II) monohydrate (Umadevi et al., 1995), dichloro[phenylbis(2-pyridyl)phosphine-N,N']cobalt(II) ethanol solvate (Ehrlich et al., 1984) and bis(N-2-propylsalicylideneamino-N,O)cobalt(II) (Elerman et al., 1996).

The molecular dimensions in the benzimidazole part of the ligand are normal while the pyrrolidinyl ring is disordered. The important bond distances are: C_sp²—Cl 1.747 (7) Å and mean C_sp³—C_sp² 1.51 (2), C—C_aromatic 1.383 (11), N—C_sp² 1.390 (4) and N—C_sp³ 1.482 (3) Å, not including the disordered pyrrolidinyl ring. It is interesting to note that the N1—C7 bond [1.340 (7) Å] is much shorter than expected for a single bond and that the N2—C7 bond [1.337 (7) Å] is much longer than a double bond; these bonds must represent a delocalized system with a mean N ≐C distance of 1.339 (2) Å; the corresponding distances in the structure of clemizoledichlorozinc(II) (Parvez & Sabir, 1996a) were 1.357 (5) and 1.321 (5) Å, respectively. The pyrrolidinyl ring in (I) is disordered over two sites with inequivalent site-occupancy factors, therefore, its N—C and C—C distances were constrained at 1.48 (1) and 1.50 (1) Å during refinement. The separation between pairs of C atoms of the pyrrolidinyl ring is in the range 0.47–0.77 Å.

The benzimidazole and phenyl rings are essentially planar, with maximum deviations of atoms from the least-squares planes being 0.013 (6) and 0.021 (4) Å, respectively. The dihedral angle between these planes is 86.2 (2)°; the corresponding angle in the structures of clemizole dichlorozinc, clemizole hydrochloride, clemizole as a free base, clemizole tetrachlorocuperate(II) and clemizole tetrachlorocobaltate(II) are 81.1 (4) (Parvez & Sabir, 1996a), 82.8 (9) (Parvez, 1996), 68.8 (6) (Parvez & Sabir, 1996b), 70.5 (6) and 82.7 (9)° (Parvez & Sabir, 1997), respectively. An examination of the N1—C8—C9—C14 torsion angle in these complex molecules shows that the orientation of the phenyl ring with respect to the imidazole ring in (I) [torsion angle 115.0 (6)°] is somewhat similar to the orientation of these rings in the free base (torsion angle 125°) and clemizole tetrachlorocobaltate(II) (torsion angle 116°); the rest of the structures have torsion angles in the range of 133–153°. The major and minor conformers of the disordered pyrrolidinyl ring have an N3-envelope conformation with N3 0.62 (5) and 0.64 (5) Å out of the planes composed of the C16–C19 and C16'–C19' atoms, respectively; a similar conformation of the five-membered ring has been observed in the crystal structures mentioned above.

The structure of (I) is composed of independent complex molecules separated by normal van der Waals distances and is devoid of any intermolecular interactions. The imidazole moieties of the molecules, which lie about inversion centers, are stacked parallel to each other.

S2. Experimental

The title compound was synthesized by adding 1.0 mmol of CoCl₂·6H₂0 to 2.0 mmol of clemizole hydrochloride in 20 ml of ethanol. NH₄OH was added until the pH was 8–9. The solution was evaporated slowly at room temperature and blue prismatic crystals separated after a few days.

S3. Refinement

The C atoms of the pyrrolidinyl ring were disordered with inequivalent site-occupancy factors 0.76 and 0.24 which were established in the early refinement cycles. In the final rounds of calculations, the site-occupancy factors of these C atoms were fixed and the atoms of the minor conformer were refined with isotropic displacement parameters; the N—C and C—C distances in the pyrrolidinyl ring were fixed at 1.48 (1) and 1.50 (1) Å, respectively, using the command DFIX in SHELXL97 (Sheldrick, 1997). H atoms were included in the refinement at idealized positions with aromatic C—H and methylene C—H distances of 0.95 and 0.99 Å, respectively. The isotropicdisplacement parameters of the H atoms were set equal to 1.2U_eq of the C atoms to which they were bonded.

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1994); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN; software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

Fig. 1. ORTEPII (Johnson, 1976) drawing of (I) with displacement ellipsoids plotted at 50% probability level. The minor fraction of the disordered pyrrolidinyl ring atoms are not shown.

Dichloro[1-(p-chlorophenylmethyl)-2-(1-pyrrolidinylmethyl)benzimidazole- N,N'']Cobalt(II)

Crystal data

[CoCl2(C19H20ClN3)]	F(000) = 932
Mr = 455.66	Dx = 1.516 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
a = 9.647 (6) Å	Cell parameters from 25 reflections
b = 12.675 (6) Å	θ = 10.0–25.0°
c = 16.359 (5) Å	µ = 1.27 mm^−1
β = 93.77 (4)°	T = 170 K
V = 1996 (2) Å^3	Prismatic, blue
Z = 4	0.40 × 0.22 × 0.16 mm

Data collection

Rigaku AFC-6S diffractometer	1425 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.097
Graphite monochromator	θmax = 25.0°, θmin = 2.5°
ω/2θ scans	h = 0→11
Absorption correction: empirical (using intensity measurements) ψ scan (3 reflections; North et al., 1968)	k = 0→15
Tmin = 0.63, Tmax = 0.82	l = −19→19
3754 measured reflections	3 standard reflections every 200 reflections
3533 independent reflections	intensity decay: none

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.136	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0384P)^2] where P = (Fo^2 + 2Fc^2)/3
3533 reflections	(Δ/σ)max < 0.001
251 parameters	Δρmax = 0.40 e Å^−3
34 restraints	Δρmin = −0.44 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Co1	0.84005 (8)	0.49515 (8)	0.68276 (5)	0.0383 (3)
Cl1	0.1710 (2)	1.07964 (15)	0.60736 (13)	0.0659 (6)
Cl2	0.91205 (18)	0.33425 (15)	0.64955 (11)	0.0542 (5)
Cl3	1.00581 (18)	0.61391 (15)	0.70886 (12)	0.0571 (5)
N1	0.4642 (5)	0.6056 (4)	0.5979 (3)	0.0398 (14)
N2	0.6872 (5)	0.5596 (4)	0.6135 (3)	0.0341 (13)
N3	0.6877 (5)	0.4875 (4)	0.7708 (3)	0.0371 (13)
C1	0.5240 (6)	0.6347 (5)	0.5259 (4)	0.0371 (17)
C2	0.4696 (7)	0.6844 (5)	0.4549 (4)	0.0408 (17)
H2	0.3744	0.7036	0.4477	0.049*
C3	0.5608 (7)	0.7042 (6)	0.3959 (4)	0.0513 (19)
H3	0.5281	0.7393	0.3471	0.062*
C4	0.7011 (7)	0.6743 (5)	0.4054 (4)	0.0446 (18)
H4	0.7602	0.6875	0.3623	0.054*
C5	0.7544 (7)	0.6259 (5)	0.4763 (4)	0.0405 (17)
H5	0.8498	0.6073	0.4834	0.049*
C6	0.6637 (6)	0.6055 (5)	0.5369 (4)	0.0366 (16)
C7	0.5645 (6)	0.5611 (5)	0.6470 (4)	0.0353 (16)
C8	0.3168 (6)	0.6190 (5)	0.6155 (4)	0.0415 (17)
H8A	0.3015	0.5876	0.6695	0.050*
H8B	0.2574	0.5806	0.5736	0.050*
C9	0.2739 (6)	0.7344 (5)	0.6157 (4)	0.0346 (15)
C10	0.3348 (6)	0.8014 (6)	0.6741 (4)	0.0413 (17)
H10	0.4006	0.7748	0.7147	0.050*
C11	0.3004 (7)	0.9063 (6)	0.6735 (4)	0.0437 (18)
H11	0.3405	0.9523	0.7144	0.052*
C12	0.2073 (7)	0.9447 (5)	0.6132 (4)	0.0400 (18)
C13	0.1423 (7)	0.8783 (6)	0.5565 (4)	0.0485 (19)
H13	0.0748	0.9047	0.5168	0.058*
C14	0.1766 (6)	0.7724 (6)	0.5579 (4)	0.0414 (17)
H14	0.1327	0.7257	0.5188	0.050*
C15	0.5513 (7)	0.5190 (6)	0.7311 (4)	0.057 (2)
H15A	0.5091	0.5736	0.7649	0.069*
H15B	0.4885	0.4572	0.7282	0.069*
C16	0.7306 (12)	0.5653 (7)	0.8370 (5)	0.050 (3)	0.76
H16A	0.6515	0.5831	0.8700	0.059*	0.76
H16B	0.7668	0.6309	0.8134	0.059*	0.76
C17	0.8437 (10)	0.5083 (8)	0.8886 (6)	0.056 (3)	0.76
H17A	0.9363	0.5244	0.8690	0.067*	0.76
H17B	0.8427	0.5295	0.9468	0.067*	0.76
C18	0.8108 (11)	0.3928 (9)	0.8785 (7)	0.068 (3)	0.76
H18A	0.7892	0.3614	0.9316	0.081*	0.76
H18B	0.8905	0.3546	0.8574	0.081*	0.76
C19	0.6855 (10)	0.3869 (7)	0.8177 (6)	0.052 (3)	0.76
H19A	0.6927	0.3255	0.7807	0.062*	0.76
H19B	0.5987	0.3806	0.8464	0.062*	0.76
C16'	0.727 (5)	0.534 (3)	0.8521 (13)	0.051 (6)*	0.24
H16C	0.6464	0.5403	0.8863	0.061*	0.24
H16D	0.7707	0.6046	0.8472	0.061*	0.24
C17'	0.830 (4)	0.453 (2)	0.885 (3)	0.048 (6)*	0.24
H17C	0.9241	0.4688	0.8680	0.057*	0.24
H17D	0.8330	0.4507	0.9458	0.057*	0.24
C18'	0.778 (4)	0.350 (2)	0.849 (2)	0.063 (6)*	0.24
H18C	0.7447	0.3043	0.8929	0.076*	0.24
H18D	0.8538	0.3132	0.8231	0.076*	0.24
C19'	0.661 (4)	0.3744 (12)	0.787 (2)	0.046 (6)*	0.24
H19C	0.6670	0.3312	0.7367	0.055*	0.24
H19D	0.5694	0.3636	0.8093	0.055*	0.24

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0285 (4)	0.0470 (5)	0.0400 (5)	0.0027 (5)	0.0065 (3)	0.0030 (5)
Cl1	0.0694 (14)	0.0401 (11)	0.0922 (16)	0.0049 (10)	0.0347 (12)	0.0068 (11)
Cl2	0.0467 (11)	0.0645 (13)	0.0505 (11)	0.0199 (9)	−0.0042 (9)	−0.0150 (10)
Cl3	0.0399 (10)	0.0549 (12)	0.0766 (14)	−0.0089 (9)	0.0040 (9)	0.0162 (11)
N1	0.031 (3)	0.038 (3)	0.051 (4)	0.002 (3)	0.008 (3)	−0.001 (3)
N2	0.030 (3)	0.039 (3)	0.034 (3)	0.004 (3)	0.005 (2)	0.001 (3)
N3	0.039 (3)	0.039 (3)	0.034 (3)	0.008 (3)	0.009 (2)	0.003 (3)
C1	0.038 (4)	0.031 (4)	0.042 (4)	−0.010 (3)	0.006 (3)	−0.003 (3)
C2	0.037 (4)	0.030 (4)	0.055 (5)	0.007 (3)	−0.002 (3)	0.006 (4)
C3	0.051 (5)	0.054 (5)	0.048 (5)	0.005 (4)	−0.001 (4)	0.014 (4)
C4	0.053 (5)	0.032 (4)	0.049 (5)	−0.004 (4)	0.011 (4)	0.004 (4)
C5	0.038 (4)	0.030 (4)	0.053 (5)	−0.002 (3)	0.004 (3)	0.000 (3)
C6	0.032 (4)	0.034 (4)	0.044 (4)	−0.005 (3)	0.012 (3)	−0.004 (3)
C7	0.033 (4)	0.036 (4)	0.038 (4)	−0.006 (3)	0.011 (3)	−0.004 (3)
C8	0.028 (4)	0.040 (4)	0.056 (5)	−0.004 (3)	0.008 (3)	0.000 (4)
C9	0.024 (3)	0.036 (4)	0.045 (4)	−0.001 (3)	0.006 (3)	−0.001 (3)
C10	0.028 (3)	0.049 (5)	0.047 (4)	0.000 (4)	0.000 (3)	−0.005 (4)
C11	0.034 (4)	0.050 (5)	0.048 (5)	−0.004 (3)	0.010 (3)	−0.010 (4)
C12	0.043 (4)	0.035 (4)	0.045 (4)	0.004 (4)	0.024 (4)	−0.001 (4)
C13	0.039 (4)	0.062 (5)	0.044 (5)	0.013 (4)	0.003 (3)	0.001 (4)
C14	0.034 (4)	0.053 (5)	0.037 (4)	−0.001 (4)	0.000 (3)	−0.012 (4)
C15	0.036 (4)	0.085 (6)	0.053 (4)	0.009 (4)	0.014 (3)	0.007 (5)
C16	0.043 (5)	0.055 (7)	0.052 (6)	0.003 (5)	0.018 (5)	−0.008 (5)
C17	0.051 (5)	0.082 (7)	0.036 (5)	0.002 (6)	0.008 (4)	−0.008 (6)
C18	0.075 (7)	0.079 (7)	0.050 (6)	0.025 (7)	0.017 (5)	0.017 (6)
C19	0.050 (6)	0.054 (6)	0.055 (7)	0.000 (5)	0.025 (5)	0.009 (5)

Geometric parameters (Å, º)

Co1—N2	1.976 (5)	C10—H10	0.9500
Co1—N3	2.126 (5)	C11—C12	1.379 (9)
Co1—Cl3	2.217 (2)	C11—H11	0.9500
Co1—Cl2	2.233 (2)	C12—C13	1.373 (9)
Cl1—C12	1.747 (7)	C13—C14	1.382 (9)
N1—C7	1.340 (7)	C13—H13	0.9500
N1—C1	1.394 (7)	C14—H14	0.9500
N1—C8	1.479 (7)	C15—H15A	0.9900
N2—C7	1.337 (7)	C15—H15B	0.9900
N2—C6	1.386 (7)	C16—C17	1.517 (8)
N3—C19'	1.482 (10)	C16—H16A	0.9900
N3—C16'	1.485 (10)	C16—H16B	0.9900
N3—C15	1.484 (8)	C17—C18	1.505 (9)
N3—C19	1.489 (7)	C17—H17A	0.9900
N3—C16	1.503 (7)	C17—H17B	0.9900
C1—C2	1.394 (8)	C18—C19	1.516 (8)
C1—C6	1.399 (8)	C18—H18A	0.9900
C2—C3	1.370 (9)	C18—H18B	0.9900
C2—H2	0.9500	C19—H19A	0.9900
C3—C4	1.404 (9)	C19—H19B	0.9900
C3—H3	0.9500	C16'—C17'	1.508 (10)
C4—C5	1.382 (8)	C16'—H16C	0.9900
C4—H4	0.9500	C16'—H16D	0.9900
C5—C6	1.389 (8)	C17'—C18'	1.501 (10)
C5—H5	0.9500	C17'—H17C	0.9900
C7—C15	1.489 (8)	C17'—H17D	0.9900
C8—C9	1.521 (8)	C18'—C19'	1.503 (10)
C8—H8A	0.9900	C18'—H18C	0.9900
C8—H8B	0.9900	C18'—H18D	0.9900
C9—C14	1.374 (8)	C19'—H19C	0.9900
C9—C10	1.381 (8)	C19'—H19D	0.9900
C10—C11	1.370 (9)
N2—Co1—N3	83.34 (18)	C13—C12—C11	120.9 (6)
N2—Co1—Cl3	109.35 (16)	C13—C12—Cl1	118.8 (6)
N3—Co1—Cl3	115.01 (15)	C11—C12—Cl1	120.2 (6)
N2—Co1—Cl2	118.05 (16)	C12—C13—C14	119.1 (7)
N3—Co1—Cl2	111.27 (15)	C12—C13—H13	120.5
Cl3—Co1—Cl2	115.79 (8)	C14—C13—H13	120.5
C7—N1—C1	107.2 (5)	C9—C14—C13	120.2 (6)
C7—N1—C8	126.7 (5)	C9—C14—H14	119.9
C1—N1—C8	126.2 (5)	C13—C14—H14	119.9
C7—N2—C6	105.6 (5)	N3—C15—C7	111.9 (5)
C7—N2—Co1	114.7 (4)	N3—C15—H15A	109.2
C6—N2—Co1	139.7 (4)	C7—C15—H15A	109.2
C19'—N3—C16'	105 (2)	N3—C15—H15B	109.2
C19'—N3—C15	100.4 (13)	C7—C15—H15B	109.2
C16'—N3—C15	116.9 (16)	H15A—C15—H15B	107.9
C19'—N3—C19	21.9 (14)	N3—C16—C17	104.1 (7)
C16'—N3—C19	83.9 (15)	N3—C16—H16A	110.9
C15—N3—C19	114.5 (6)	C17—C16—H16A	110.9
C19'—N3—C16	123.3 (15)	N3—C16—H16B	110.9
C16'—N3—C16	17.9 (17)	C17—C16—H16B	110.9
C15—N3—C16	109.5 (6)	H16A—C16—H16B	109.0
C19—N3—C16	101.7 (6)	C18—C17—C16	105.2 (7)
C19'—N3—Co1	107.4 (17)	C18—C17—H17A	110.7
C16'—N3—Co1	116.2 (19)	C16—C17—H17A	110.7
C15—N3—Co1	108.9 (3)	C18—C17—H17B	110.7
C19—N3—Co1	115.0 (5)	C16—C17—H17B	110.7
C16—N3—Co1	106.7 (5)	H17A—C17—H17B	108.8
N1—C1—C2	132.1 (6)	C17—C18—C19	105.9 (7)
N1—C1—C6	105.7 (6)	C17—C18—H18A	110.6
C2—C1—C6	122.2 (6)	C19—C18—H18A	110.6
C3—C2—C1	116.5 (6)	C17—C18—H18B	110.6
C3—C2—H2	121.8	C19—C18—H18B	110.6
C1—C2—H2	121.8	H18A—C18—H18B	108.7
C2—C3—C4	122.1 (6)	N3—C19—C18	104.9 (7)
C2—C3—H3	118.9	N3—C19—H19A	110.8
C4—C3—H3	118.9	C18—C19—H19A	110.8
C5—C4—C3	121.0 (6)	N3—C19—H19B	110.8
C5—C4—H4	119.5	C18—C19—H19B	110.8
C3—C4—H4	119.5	H19A—C19—H19B	108.8
C4—C5—C6	117.7 (6)	N3—C16'—C17'	100 (2)
C4—C5—H5	121.1	N3—C16'—H16C	111.8
C6—C5—H5	121.1	C17'—C16'—H16C	111.8
N2—C6—C5	130.6 (6)	N3—C16'—H16D	111.8
N2—C6—C1	109.0 (5)	C17'—C16'—H16D	111.8
C5—C6—C1	120.4 (6)	H16C—C16'—H16D	109.5
N2—C7—N1	112.6 (5)	C18'—C17'—C16'	105 (3)
N2—C7—C15	120.4 (6)	C18'—C17'—H17C	110.7
N1—C7—C15	127.0 (6)	C16'—C17'—H17C	110.7
N1—C8—C9	112.1 (5)	C18'—C17'—H17D	110.7
N1—C8—H8A	109.2	C16'—C17'—H17D	110.7
C9—C8—H8A	109.2	H17C—C17'—H17D	108.8
N1—C8—H8B	109.2	C17'—C18'—C19'	108 (3)
C9—C8—H8B	109.2	C17'—C18'—H18C	110.2
H8A—C8—H8B	107.9	C19'—C18'—H18C	110.2
C14—C9—C10	120.1 (6)	C17'—C18'—H18D	110.2
C14—C9—C8	120.6 (6)	C19'—C18'—H18D	110.2
C10—C9—C8	119.3 (6)	H18C—C18'—H18D	108.5
C11—C10—C9	120.0 (6)	N3—C19'—C18'	100.8 (19)
C11—C10—H10	120.0	N3—C19'—H19C	111.6
C9—C10—H10	120.0	C18'—C19'—H19C	111.6
C10—C11—C12	119.6 (7)	N3—C19'—H19D	111.6
C10—C11—H11	120.2	C18'—C19'—H19D	111.6
C12—C11—H11	120.2	H19C—C19'—H19D	109.4
N3—Co1—N2—C7	−5.1 (4)	C7—N1—C8—C9	119.4 (7)
Cl3—Co1—N2—C7	−119.3 (4)	C1—N1—C8—C9	−62.3 (8)
Cl2—Co1—N2—C7	105.5 (4)	N1—C8—C9—C14	115.0 (6)
N3—Co1—N2—C6	175.7 (7)	N1—C8—C9—C10	−64.3 (8)
Cl3—Co1—N2—C6	61.5 (7)	C14—C9—C10—C11	−1.3 (9)
Cl2—Co1—N2—C6	−73.7 (7)	C8—C9—C10—C11	178.0 (5)
N2—Co1—N3—C19'	115.3 (12)	C9—C10—C11—C12	−1.5 (9)
Cl3—Co1—N3—C19'	−136.4 (12)	C10—C11—C12—C13	3.8 (9)
Cl2—Co1—N3—C19'	−2.3 (12)	C10—C11—C12—Cl1	−175.6 (5)
N2—Co1—N3—C16'	−127.0 (15)	C11—C12—C13—C14	−3.2 (10)
Cl3—Co1—N3—C16'	−18.7 (15)	Cl1—C12—C13—C14	176.3 (5)
Cl2—Co1—N3—C16'	115.4 (15)	C10—C9—C14—C13	1.9 (9)
N2—Co1—N3—C15	7.4 (5)	C8—C9—C14—C13	−177.4 (6)
Cl3—Co1—N3—C15	115.7 (4)	C12—C13—C14—C9	0.3 (10)
Cl2—Co1—N3—C15	−110.1 (4)	C19'—N3—C15—C7	−120.9 (18)
N2—Co1—N3—C19	137.4 (5)	C16'—N3—C15—C7	126 (2)
Cl3—Co1—N3—C19	−114.3 (5)	C19—N3—C15—C7	−138.6 (7)
Cl2—Co1—N3—C19	19.8 (5)	C16—N3—C15—C7	108.0 (7)
N2—Co1—N3—C16	−110.7 (5)	Co1—N3—C15—C7	−8.3 (7)
Cl3—Co1—N3—C16	−2.4 (5)	N2—C7—C15—N3	5.0 (9)
Cl2—Co1—N3—C16	131.8 (4)	N1—C7—C15—N3	−173.0 (6)
C7—N1—C1—C2	−179.3 (6)	C19'—N3—C16—C17	46 (2)
C8—N1—C1—C2	2.1 (10)	C16'—N3—C16—C17	46 (6)
C7—N1—C1—C6	−0.6 (7)	C15—N3—C16—C17	163.2 (7)
C8—N1—C1—C6	−179.1 (5)	C19—N3—C16—C17	41.7 (9)
N1—C1—C2—C3	178.1 (7)	Co1—N3—C16—C17	−79.1 (7)
C6—C1—C2—C3	−0.5 (9)	N3—C16—C17—C18	−27.9 (10)
C1—C2—C3—C4	1.3 (10)	C16—C17—C18—C19	3.3 (11)
C2—C3—C4—C5	−2.0 (11)	C19'—N3—C19—C18	149 (5)
C3—C4—C5—C6	1.7 (10)	C16'—N3—C19—C18	−40.8 (19)
C7—N2—C6—C5	178.9 (6)	C15—N3—C19—C18	−157.6 (7)
Co1—N2—C6—C5	−2.0 (11)	C16—N3—C19—C18	−39.7 (9)
C7—N2—C6—C1	0.3 (7)	Co1—N3—C19—C18	75.2 (8)
Co1—N2—C6—C1	179.5 (5)	C17—C18—C19—N3	22.7 (10)
C4—C5—C6—N2	−179.3 (6)	C19'—N3—C16'—C17'	46 (4)
C4—C5—C6—C1	−0.9 (9)	C15—N3—C16'—C17'	157 (2)
N1—C1—C6—N2	0.2 (7)	C19—N3—C16'—C17'	43 (3)
C2—C1—C6—N2	179.1 (5)	C16—N3—C16'—C17'	−134 (9)
N1—C1—C6—C5	−178.6 (5)	Co1—N3—C16'—C17'	−72 (3)
C2—C1—C6—C5	0.3 (9)	N3—C16'—C17'—C18'	−33 (4)
C6—N2—C7—N1	−0.7 (7)	C16'—C17'—C18'—C19'	9 (5)
Co1—N2—C7—N1	179.9 (4)	C16'—N3—C19'—C18'	−41 (3)
C6—N2—C7—C15	−179.0 (6)	C15—N3—C19'—C18'	−163 (2)
Co1—N2—C7—C15	1.6 (8)	C19—N3—C19'—C18'	−30 (3)
C1—N1—C7—N2	0.8 (7)	C16—N3—C19'—C18'	−41 (3)
C8—N1—C7—N2	179.4 (5)	Co1—N3—C19'—C18'	83 (3)
C1—N1—C7—C15	178.9 (6)	C17'—C18'—C19'—N3	19 (4)
C8—N1—C7—C15	−2.5 (10)