Variable-temperature structural studies on valence tautomerism in cobalt bis­(dioxolene) molecular complexes

A variable-temperature single-crystal structural study of five valence tautomeric cobalt molecular complexes, Co^II(3,5-DBSQ)₂(DBPy)₂ (1), Co^II(3,5-DBSQ)₂(DBPy)₂·1.33C₇H₈ (1S), Co^II(3,5-DBSQ)₂(DCPy)₂·C₇H₈ (2S), Co^II(3,5-DBSQ)₂(TBPy)₂ (3) and Co^II(3,5-DBSQ)₂(TCPy)₂ (4) (S = toluene, 3,5-DBSQ = 3,5-di-tert-butylsemiquinonate, DBPy = 3,5-dibromopyridine, DCPy = 3,5-dichloropyridine, TBPy = 3,4,5-tribromopyridine and TCPy = 3,4,5-trichloropyridine) is reported. The re-crystallization of (1S) in toluene at 277 K resulted in a concomitant formation of a solvent-free polymorph, Co^II(3,5-DBSQ)₂(DBPy)₂ (1). Thermally induced valence tautomerism (VT) is observed only in (1S), (1) and (2S) [hs-Co^II(3,5-DBSQ)₂L₂ ↔ ls-Co^III(3,5-DBSQ)(3,5-DBCat)L₂ (hs = high spin, ls = low spin, 3,5-DBCat = 3,5-di-tert-butylcatecholate)], whereas (3) and (4) remain locked in the hs-Co^II(3,5-DBSQ)₂ state during cooling of the sample. Multi-temperature single-crystal studies demonstrate the change in cobalt coordination environment during the VT conversion. The non-solvated compound (1) shows a sharp VT transition (T_1/2 ∼ 245 K with ΔT ∼ 10 K) from hs-Co^II(3,5-DBSQ)₂(DBPy)₂ to ls-Co^III(3,5-DBSQ)(3,5-DBCat)(DBPy)₂ oxidation state, whereas the other polymorph with lattice solvent (1S) results in a broad transition (T_1/2 ∼ 150 K with ΔT ∼ 100 K). This increase in the VT transition temperature for (1) relative to (1S) illustrates the effect of lattice solvent on the VT transition mechanism. Additionally, the influence of halogen substitutions on the pyridine ring is discussed with respect to observed VT behaviour in the studied compounds.

Computing details

For all compounds, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2014).

(1_100K)

Crystal data

C38H46Br4CoN2O4	Z = 1
Mr = 973.34	F(000) = 487
Triclinic, P1	Dx = 1.707 Mg m^−3
a = 8.9545 (6) Å	Ag Kα radiation, λ = 0.56085 Å
b = 10.1012 (6) Å	Cell parameters from 22010 reflections
c = 11.5659 (8) Å	θ = 1.4–20.6°
α = 85.879 (3)°	µ = 2.52 mm^−1
β = 89.310 (4)°	T = 100 K
γ = 65.160 (3)°	Block, green
V = 946.72 (11) Å^3	0.20 × 0.17 × 0.14 mm

Data collection

Bruker Kappa APEX II CCD detector diffractometer	3770 independent reflections
Radiation source: Bruker, Kappa Apex II	3122 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.053
φ and ω scans	θmax = 20.6°, θmin = 1.4°
Absorption correction: multi-scan Bruker AXS, 2008	h = −11→10
Tmin = 0.632, Tmax = 0.719	k = −12→12
22010 measured reflections	l = −14→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.129	w = 1/[σ^2(Fo^2) + (0.0793P)^2 + 0.9045P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
3770 reflections	Δρmax = 1.94 e Å^−3
229 parameters	Δρmin = −1.05 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.4463 (5)	0.6134 (4)	0.2034 (3)	0.0148 (8)
C2	0.3133 (5)	0.5744 (4)	0.1857 (3)	0.0149 (8)
C3	0.1846 (5)	0.6072 (4)	0.2671 (3)	0.0162 (8)
C4	0.1988 (5)	0.6773 (4)	0.3634 (3)	0.0199 (8)
H4	0.1131	0.7030	0.4182	0.024*
C5	0.3321 (5)	0.7119 (4)	0.3843 (3)	0.0186 (8)
C6	0.4547 (5)	0.6810 (4)	0.3028 (3)	0.0173 (8)
H6	0.5444	0.7058	0.3145	0.021*
C7	0.0468 (5)	0.5594 (4)	0.2534 (3)	0.0197 (8)
C8	−0.0360 (5)	0.6064 (5)	0.1330 (4)	0.0239 (9)
H8A	−0.1338	0.5861	0.1315	0.036*
H8B	0.0413	0.5518	0.0747	0.036*
H8C	−0.0686	0.7114	0.1159	0.036*
C9	0.1173 (6)	0.3918 (5)	0.2712 (4)	0.0308 (10)
H9A	0.1669	0.3600	0.3491	0.046*
H9B	0.2013	0.3482	0.2133	0.046*
H9C	0.0286	0.3603	0.2626	0.046*
C10	−0.0877 (5)	0.6205 (5)	0.3442 (4)	0.0248 (9)
H10A	−0.0388	0.5874	0.4222	0.037*
H10B	−0.1728	0.5853	0.3329	0.037*
H10C	−0.1372	0.7276	0.3353	0.037*
C11	0.3395 (5)	0.7845 (5)	0.4954 (3)	0.0218 (9)
C13	0.5158 (8)	0.7511 (10)	0.5291 (6)	0.072 (2)
H13A	0.5605	0.8001	0.4716	0.108*
H13B	0.5826	0.6452	0.5320	0.108*
H13C	0.5181	0.7864	0.6055	0.108*
C12	0.2694 (9)	0.7263 (7)	0.5969 (4)	0.0527 (17)
H12A	0.2900	0.7623	0.6687	0.079*
H12B	0.3224	0.6191	0.6026	0.079*
H12C	0.1505	0.7600	0.5847	0.079*
C14	0.2417 (10)	0.9482 (5)	0.4773 (5)	0.059 (2)
H14A	0.2486	0.9939	0.5478	0.089*
H14B	0.1263	0.9704	0.4603	0.089*
H14C	0.2866	0.9866	0.4123	0.089*
C15	0.5644 (5)	0.2103 (4)	0.0889 (3)	0.0192 (8)
H15	0.4506	0.2413	0.0722	0.023*
C16	0.6560 (5)	0.0702 (4)	0.1365 (4)	0.0213 (9)
C17	0.8219 (5)	0.0221 (4)	0.1578 (3)	0.0189 (8)
H17	0.8858	−0.0738	0.1914	0.023*
C18	0.8920 (5)	0.1167 (4)	0.1291 (3)	0.0177 (8)
C19	0.7960 (5)	0.2586 (4)	0.0854 (3)	0.0173 (8)
H19	0.8451	0.3248	0.0691	0.021*
N1	0.6344 (4)	0.3031 (3)	0.0659 (3)	0.0159 (7)
O1	0.5607 (3)	0.5803 (3)	0.1234 (2)	0.0164 (6)
O2	0.3204 (3)	0.5060 (3)	0.0905 (2)	0.0160 (6)
Co1	0.5000	0.5000	0.0000	0.01392 (19)
Br1	1.12040 (5)	0.05595 (4)	0.15042 (3)	0.02452 (15)
Br2	0.55065 (5)	−0.05424 (4)	0.17038 (4)	0.03272 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0096 (18)	0.0136 (17)	0.0184 (17)	−0.0025 (14)	−0.0025 (14)	0.0013 (14)
C2	0.0136 (18)	0.0119 (17)	0.0154 (17)	−0.0018 (15)	−0.0022 (14)	0.0006 (13)
C3	0.0110 (18)	0.0155 (17)	0.0196 (18)	−0.0039 (15)	−0.0040 (14)	0.0041 (14)
C4	0.016 (2)	0.0212 (19)	0.0193 (18)	−0.0052 (16)	0.0019 (15)	−0.0015 (15)
C5	0.0147 (19)	0.0159 (18)	0.0225 (19)	−0.0038 (16)	−0.0026 (15)	−0.0022 (15)
C6	0.0150 (19)	0.0191 (18)	0.0192 (18)	−0.0087 (16)	−0.0029 (15)	0.0002 (14)
C7	0.015 (2)	0.0219 (19)	0.0232 (19)	−0.0086 (16)	−0.0007 (16)	0.0011 (15)
C8	0.017 (2)	0.030 (2)	0.027 (2)	−0.0119 (18)	0.0010 (17)	−0.0081 (17)
C9	0.022 (2)	0.025 (2)	0.048 (3)	−0.0120 (19)	0.004 (2)	−0.0022 (19)
C10	0.017 (2)	0.033 (2)	0.027 (2)	−0.0128 (19)	0.0002 (17)	−0.0016 (17)
C11	0.019 (2)	0.027 (2)	0.0215 (19)	−0.0110 (18)	−0.0016 (16)	−0.0062 (16)
C13	0.032 (3)	0.133 (7)	0.056 (4)	−0.030 (4)	0.005 (3)	−0.064 (4)
C12	0.095 (5)	0.064 (4)	0.022 (2)	−0.056 (4)	0.003 (3)	−0.007 (2)
C14	0.100 (5)	0.019 (2)	0.038 (3)	−0.003 (3)	−0.021 (3)	−0.011 (2)
C15	0.0124 (19)	0.0201 (19)	0.0232 (19)	−0.0052 (16)	0.0000 (15)	0.0001 (15)
C16	0.019 (2)	0.021 (2)	0.029 (2)	−0.0129 (17)	0.0024 (17)	−0.0037 (16)
C17	0.017 (2)	0.0192 (18)	0.0223 (19)	−0.0090 (16)	−0.0015 (16)	−0.0002 (15)
C18	0.0106 (18)	0.0229 (19)	0.0199 (18)	−0.0069 (16)	0.0000 (14)	−0.0045 (15)
C19	0.0138 (19)	0.0211 (19)	0.0171 (18)	−0.0078 (16)	−0.0006 (15)	0.0017 (14)
N1	0.0125 (16)	0.0175 (15)	0.0180 (15)	−0.0062 (13)	−0.0009 (12)	−0.0032 (12)
O1	0.0136 (14)	0.0185 (13)	0.0180 (13)	−0.0074 (11)	−0.0016 (10)	−0.0019 (10)
O2	0.0107 (13)	0.0177 (13)	0.0202 (13)	−0.0063 (11)	0.0005 (10)	−0.0022 (10)
Co1	0.0104 (4)	0.0149 (4)	0.0164 (4)	−0.0052 (3)	−0.0008 (3)	−0.0012 (3)
Br1	0.0132 (2)	0.0253 (2)	0.0328 (2)	−0.00620 (18)	−0.00629 (16)	0.00088 (17)
Br2	0.0185 (3)	0.0205 (2)	0.0594 (3)	−0.01045 (19)	−0.0078 (2)	0.01157 (19)

Geometric parameters (Å, º)

C1—O1	1.323 (4)	C11—C13	1.519 (7)
C1—C6	1.398 (5)	C15—N1	1.340 (5)
C1—C2	1.423 (6)	C15—C16	1.379 (6)
C2—O2	1.328 (4)	C16—C17	1.374 (6)
C2—C3	1.423 (5)	C16—Br2	1.882 (4)
C3—C4	1.397 (6)	C17—C18	1.368 (6)
C3—C7	1.515 (6)	C18—C19	1.386 (5)
C4—C5	1.406 (6)	C18—Br1	1.886 (4)
C5—C6	1.386 (5)	C19—N1	1.339 (5)
C5—C11	1.539 (5)	N1—Co1	1.943 (3)
C7—C8	1.532 (6)	O1—Co1	1.883 (3)
C7—C9	1.538 (6)	O2—Co1	1.890 (3)
C7—C10	1.541 (5)	Co1—O1^i	1.883 (3)
C11—C14	1.512 (6)	Co1—O2^i	1.890 (3)
C11—C12	1.520 (7)	Co1—N1^i	1.943 (3)
O1—C1—C6	122.4 (4)	C17—C16—Br2	120.6 (3)
O1—C1—C2	117.2 (3)	C15—C16—Br2	119.0 (3)
C6—C1—C2	120.4 (3)	C18—C17—C16	117.8 (4)
O2—C2—C3	123.9 (4)	C17—C18—C19	120.5 (4)
O2—C2—C1	115.5 (3)	C17—C18—Br1	120.2 (3)
C3—C2—C1	120.6 (3)	C19—C18—Br1	119.3 (3)
C4—C3—C2	116.0 (4)	N1—C19—C18	120.4 (4)
C4—C3—C7	122.3 (3)	C19—N1—C15	120.0 (3)
C2—C3—C7	121.5 (3)	C19—N1—Co1	120.7 (3)
C3—C4—C5	124.1 (4)	C15—N1—Co1	119.2 (3)
C6—C5—C4	118.8 (4)	C1—O1—Co1	109.6 (2)
C6—C5—C11	121.0 (4)	C2—O2—Co1	110.1 (2)
C4—C5—C11	120.2 (3)	O1^i—Co1—O1	180.0
C5—C6—C1	120.0 (4)	O1^i—Co1—O2^i	87.09 (11)
C3—C7—C8	112.2 (3)	O1—Co1—O2^i	92.91 (11)
C3—C7—C9	109.2 (3)	O1^i—Co1—O2	92.91 (11)
C8—C7—C9	108.3 (4)	O1—Co1—O2	87.09 (11)
C3—C7—C10	112.4 (3)	O2^i—Co1—O2	180.0
C8—C7—C10	107.8 (3)	O1^i—Co1—N1	89.22 (12)
C9—C7—C10	106.7 (3)	O1—Co1—N1	90.78 (12)
C14—C11—C12	109.0 (5)	O2^i—Co1—N1	89.54 (12)
C14—C11—C13	109.3 (5)	O2—Co1—N1	90.46 (12)
C12—C11—C13	106.7 (5)	O1^i—Co1—N1^i	90.78 (12)
C14—C11—C5	109.9 (3)	O1—Co1—N1^i	89.22 (12)
C12—C11—C5	110.6 (4)	O2^i—Co1—N1^i	90.46 (12)
C13—C11—C5	111.3 (4)	O2—Co1—N1^i	89.54 (12)
N1—C15—C16	120.7 (4)	N1—Co1—N1^i	180.0
C17—C16—C15	120.4 (4)
O1—C1—C2—O2	1.1 (5)	C6—C5—C11—C13	−26.5 (6)
C6—C1—C2—O2	−177.7 (3)	C4—C5—C11—C13	154.2 (5)
O1—C1—C2—C3	−179.5 (3)	N1—C15—C16—C17	−2.0 (6)
C6—C1—C2—C3	1.8 (5)	N1—C15—C16—Br2	178.6 (3)
O2—C2—C3—C4	178.8 (3)	C15—C16—C17—C18	−0.7 (6)
C1—C2—C3—C4	−0.6 (5)	Br2—C16—C17—C18	178.7 (3)
O2—C2—C3—C7	2.8 (5)	C16—C17—C18—C19	3.1 (6)
C1—C2—C3—C7	−176.6 (3)	C16—C17—C18—Br1	−177.6 (3)
C2—C3—C4—C5	−1.7 (6)	C17—C18—C19—N1	−2.9 (6)
C7—C3—C4—C5	174.3 (4)	Br1—C18—C19—N1	177.8 (3)
C3—C4—C5—C6	2.8 (6)	C18—C19—N1—C15	0.1 (5)
C3—C4—C5—C11	−177.8 (4)	C18—C19—N1—Co1	−178.1 (3)
C4—C5—C6—C1	−1.5 (6)	C16—C15—N1—C19	2.3 (5)
C11—C5—C6—C1	179.2 (3)	C16—C15—N1—Co1	−179.5 (3)
O1—C1—C6—C5	−179.4 (3)	C6—C1—O1—Co1	−177.0 (3)
C2—C1—C6—C5	−0.7 (5)	C2—C1—O1—Co1	4.2 (4)
C4—C3—C7—C8	131.9 (4)	C3—C2—O2—Co1	174.8 (3)
C2—C3—C7—C8	−52.3 (5)	C1—C2—O2—Co1	−5.8 (4)
C4—C3—C7—C9	−108.0 (4)	C1—O1—Co1—O2^i	174.1 (2)
C2—C3—C7—C9	67.7 (4)	C1—O1—Co1—O2	−5.9 (2)
C4—C3—C7—C10	10.2 (5)	C1—O1—Co1—N1	−96.3 (2)
C2—C3—C7—C10	−174.1 (3)	C1—O1—Co1—N1^i	83.7 (2)
C6—C5—C11—C14	94.7 (5)	C2—O2—Co1—O1^i	−173.5 (2)
C4—C5—C11—C14	−84.7 (5)	C2—O2—Co1—O1	6.5 (2)
C6—C5—C11—C12	−144.9 (5)	C2—O2—Co1—N1	97.3 (2)
C4—C5—C11—C12	35.8 (6)	C2—O2—Co1—N1^i	−82.7 (2)

Symmetry code: (i) −x+1, −y+1, −z.

(1_150K)

Crystal data

C38H46Br4CoN2O4	Z = 1
Mr = 973.34	F(000) = 487
Triclinic, P1	Dx = 1.698 Mg m^−3
a = 8.9612 (7) Å	Ag Kα radiation, λ = 0.56085 Å
b = 10.1111 (8) Å	Cell parameters from 17278 reflections
c = 11.5984 (9) Å	θ = 1.4–20.0°
α = 85.951 (5)°	µ = 2.51 mm^−1
β = 89.290 (3)°	T = 150 K
γ = 65.221 (4)°	Block, blue
V = 951.59 (13) Å^3	0.20 × 0.17 × 0.14 mm

Data collection

Bruker Kappa APEX II CCD detector diffractometer	3411 independent reflections
Radiation source: Bruker, Kappa Apex II	2731 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.044
φ and ω scans	θmax = 20.0°, θmin = 1.4°
Absorption correction: multi-scan Bruker AXS, 2008	h = −10→10
Tmin = 0.634, Tmax = 0.720	k = −12→12
17278 measured reflections	l = −14→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.120	w = 1/[σ^2(Fo^2) + (0.0697P)^2 + 0.3802P] where P = (Fo^2 + 2Fc^2)/3
S = 1.16	(Δ/σ)max = 0.001
3411 reflections	Δρmax = 1.33 e Å^−3
229 parameters	Δρmin = −0.82 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.5543 (5)	0.3859 (4)	0.7966 (3)	0.0163 (8)
C2	0.6861 (5)	0.4251 (4)	0.8148 (3)	0.0160 (8)
C3	0.8145 (5)	0.3923 (4)	0.7338 (3)	0.0177 (8)
C4	0.7996 (5)	0.3230 (4)	0.6373 (3)	0.0224 (9)
H4	0.8848	0.2982	0.5824	0.027*
C5	0.6680 (5)	0.2877 (4)	0.6160 (3)	0.0219 (9)
C6	0.5443 (5)	0.3191 (4)	0.6977 (3)	0.0200 (9)
H6	0.4540	0.2952	0.6859	0.024*
C7	0.9521 (5)	0.4403 (4)	0.7472 (3)	0.0222 (9)
C8	0.8827 (6)	0.6072 (5)	0.7314 (5)	0.0382 (12)
H8A	0.7999	0.6499	0.7901	0.057*
H8B	0.8318	0.6403	0.6542	0.057*
H8C	0.9718	0.6381	0.7397	0.057*
C9	1.0356 (6)	0.3923 (5)	0.8669 (4)	0.0294 (10)
H9A	1.1337	0.4119	0.8683	0.044*
H9B	1.0674	0.2875	0.8835	0.044*
H9C	0.9590	0.4467	0.9255	0.044*
C10	1.0862 (6)	0.3794 (5)	0.6570 (4)	0.0306 (11)
H10A	1.1725	0.4127	0.6694	0.046*
H10B	1.0379	0.4142	0.5792	0.046*
H10C	1.1336	0.2724	0.6646	0.046*
C11	0.6592 (6)	0.2162 (5)	0.5055 (4)	0.0266 (10)
C12	0.7273 (11)	0.2758 (8)	0.4044 (4)	0.068 (2)
H12A	0.6746	0.3828	0.4000	0.103*
H12B	0.7049	0.2413	0.3325	0.103*
H12C	0.8462	0.2419	0.4152	0.103*
C13	0.4856 (9)	0.2479 (11)	0.4724 (6)	0.088 (3)
H13A	0.4433	0.1946	0.5276	0.132*
H13B	0.4829	0.2169	0.3946	0.132*
H13C	0.4171	0.3530	0.4734	0.132*
C14	0.7586 (10)	0.0530 (6)	0.5232 (5)	0.075 (2)
H14A	0.8729	0.0322	0.5421	0.112*
H14B	0.7547	0.0073	0.4522	0.112*
H14C	0.7127	0.0136	0.5868	0.112*
C15	0.4365 (5)	0.7887 (4)	0.9113 (3)	0.0205 (9)
H15	0.5502	0.7577	0.9279	0.025*
C16	0.3446 (6)	0.9282 (4)	0.8639 (4)	0.0248 (10)
C17	0.1800 (5)	0.9762 (4)	0.8423 (3)	0.0236 (9)
H17	0.1165	1.0719	0.8088	0.028*
C18	0.1099 (5)	0.8819 (4)	0.8705 (3)	0.0213 (9)
C19	0.2057 (5)	0.7406 (4)	0.9140 (3)	0.0211 (9)
H19	0.1566	0.6744	0.9299	0.025*
N1	0.3655 (4)	0.6965 (3)	0.9338 (3)	0.0175 (7)
O1	0.4390 (3)	0.4196 (3)	0.8770 (2)	0.0185 (6)
O2	0.6799 (3)	0.4931 (3)	0.9101 (2)	0.0171 (6)
Co1	0.5000	0.5000	1.0000	0.0153 (2)
Br1	−0.11796 (5)	0.94272 (5)	0.84919 (4)	0.03098 (17)
Br2	0.45099 (6)	1.05180 (5)	0.82986 (5)	0.04170 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.011 (2)	0.0141 (17)	0.0203 (19)	−0.0021 (15)	−0.0001 (16)	0.0011 (14)
C2	0.013 (2)	0.0133 (18)	0.0196 (19)	−0.0031 (15)	−0.0024 (16)	0.0016 (14)
C3	0.014 (2)	0.0171 (18)	0.0222 (19)	−0.0074 (16)	−0.0009 (16)	0.0011 (15)
C4	0.017 (2)	0.024 (2)	0.022 (2)	−0.0049 (17)	0.0024 (17)	−0.0029 (16)
C5	0.019 (2)	0.0174 (19)	0.026 (2)	−0.0039 (16)	−0.0012 (17)	−0.0031 (15)
C6	0.018 (2)	0.0204 (19)	0.021 (2)	−0.0080 (17)	−0.0001 (17)	−0.0006 (15)
C7	0.014 (2)	0.025 (2)	0.028 (2)	−0.0087 (17)	0.0013 (18)	0.0002 (16)
C8	0.025 (3)	0.027 (2)	0.066 (3)	−0.015 (2)	0.004 (2)	0.000 (2)
C9	0.019 (2)	0.038 (2)	0.036 (2)	−0.016 (2)	0.001 (2)	−0.0100 (19)
C10	0.019 (2)	0.044 (3)	0.031 (2)	−0.016 (2)	0.002 (2)	−0.0013 (19)
C11	0.026 (3)	0.030 (2)	0.024 (2)	−0.0115 (19)	0.0009 (19)	−0.0064 (17)
C12	0.131 (7)	0.081 (4)	0.025 (3)	−0.075 (5)	0.009 (3)	−0.010 (3)
C13	0.045 (4)	0.164 (8)	0.065 (4)	−0.042 (5)	0.009 (3)	−0.080 (5)
C14	0.125 (7)	0.026 (3)	0.050 (3)	−0.005 (3)	−0.022 (4)	−0.016 (2)
C15	0.011 (2)	0.023 (2)	0.027 (2)	−0.0071 (16)	−0.0011 (17)	−0.0015 (16)
C16	0.027 (3)	0.021 (2)	0.031 (2)	−0.0139 (18)	0.0048 (19)	−0.0044 (17)
C17	0.020 (2)	0.025 (2)	0.026 (2)	−0.0099 (17)	−0.0014 (18)	−0.0003 (16)
C18	0.014 (2)	0.027 (2)	0.023 (2)	−0.0084 (17)	−0.0010 (17)	−0.0044 (16)
C19	0.022 (2)	0.024 (2)	0.0206 (19)	−0.0122 (17)	0.0009 (18)	−0.0016 (15)
N1	0.0143 (19)	0.0178 (16)	0.0204 (16)	−0.0068 (13)	−0.0004 (14)	−0.0017 (12)
O1	0.0127 (15)	0.0221 (14)	0.0215 (14)	−0.0079 (11)	0.0008 (11)	−0.0037 (11)
O2	0.0121 (15)	0.0186 (13)	0.0215 (13)	−0.0074 (11)	0.0000 (11)	−0.0021 (10)
Co1	0.0115 (4)	0.0158 (4)	0.0195 (4)	−0.0065 (3)	0.0005 (3)	−0.0020 (3)
Br1	0.0161 (3)	0.0319 (3)	0.0427 (3)	−0.00823 (19)	−0.00787 (19)	0.00124 (19)
Br2	0.0237 (3)	0.0251 (3)	0.0781 (4)	−0.0147 (2)	−0.0087 (2)	0.0156 (2)

Geometric parameters (Å, º)

C1—O1	1.335 (4)	C12—H12A	0.9800
C1—C6	1.394 (6)	C12—H12B	0.9800
C1—C2	1.416 (6)	C12—H12C	0.9800
C2—O2	1.331 (5)	C13—H13A	0.9800
C2—C3	1.419 (5)	C13—H13B	0.9800
C3—C4	1.398 (6)	C13—H13C	0.9800
C3—C7	1.516 (6)	C14—H14A	0.9800
C4—C5	1.397 (7)	C14—H14B	0.9800
C4—H4	0.9500	C14—H14C	0.9800
C5—C6	1.396 (6)	C15—N1	1.342 (5)
C5—C11	1.533 (6)	C15—C16	1.378 (6)
C6—H6	0.9500	C15—H15	0.9500
C7—C8	1.532 (6)	C16—C17	1.365 (6)
C7—C9	1.533 (6)	C16—Br2	1.883 (4)
C7—C10	1.536 (6)	C17—C18	1.365 (6)
C8—H8A	0.9800	C17—H17	0.9500
C8—H8B	0.9800	C18—C19	1.384 (6)
C8—H8C	0.9800	C18—Br1	1.883 (4)
C9—H9A	0.9800	C19—N1	1.327 (5)
C9—H9B	0.9800	C19—H19	0.9500
C9—H9C	0.9800	N1—Co1	1.947 (3)
C10—H10A	0.9800	O1—Co1	1.883 (3)
C10—H10B	0.9800	O2—Co1	1.888 (3)
C10—H10C	0.9800	Co1—O1^i	1.883 (3)
C11—C13	1.501 (8)	Co1—O2^i	1.888 (3)
C11—C14	1.511 (6)	Co1—N1^i	1.947 (3)
C11—C12	1.518 (7)
O1—C1—C6	122.0 (4)	C11—C12—H12C	109.5
O1—C1—C2	116.7 (3)	H12A—C12—H12C	109.5
C6—C1—C2	121.3 (3)	H12B—C12—H12C	109.5
O2—C2—C1	116.1 (3)	C11—C13—H13A	109.5
O2—C2—C3	123.6 (4)	C11—C13—H13B	109.5
C1—C2—C3	120.3 (3)	H13A—C13—H13B	109.5
C4—C3—C2	116.0 (4)	C11—C13—H13C	109.5
C4—C3—C7	122.3 (3)	H13A—C13—H13C	109.5
C2—C3—C7	121.6 (3)	H13B—C13—H13C	109.5
C5—C4—C3	124.6 (4)	C11—C14—H14A	109.5
C5—C4—H4	117.7	C11—C14—H14B	109.5
C3—C4—H4	117.7	H14A—C14—H14B	109.5
C6—C5—C4	118.4 (4)	C11—C14—H14C	109.5
C6—C5—C11	120.7 (4)	H14A—C14—H14C	109.5
C4—C5—C11	120.9 (4)	H14B—C14—H14C	109.5
C1—C6—C5	119.4 (4)	N1—C15—C16	120.0 (4)
C1—C6—H6	120.3	N1—C15—H15	120.0
C5—C6—H6	120.3	C16—C15—H15	120.0
C3—C7—C8	109.6 (3)	C17—C16—C15	120.9 (4)
C3—C7—C9	111.9 (3)	C17—C16—Br2	120.7 (3)
C8—C7—C9	108.0 (4)	C15—C16—Br2	118.4 (3)
C3—C7—C10	112.5 (4)	C18—C17—C16	117.7 (4)
C8—C7—C10	107.2 (3)	C18—C17—H17	121.1
C9—C7—C10	107.5 (4)	C16—C17—H17	121.1
C7—C8—H8A	109.5	C17—C18—C19	120.3 (4)
C7—C8—H8B	109.5	C17—C18—Br1	120.2 (3)
H8A—C8—H8B	109.5	C19—C18—Br1	119.5 (3)
C7—C8—H8C	109.5	N1—C19—C18	120.7 (4)
H8A—C8—H8C	109.5	N1—C19—H19	119.7
H8B—C8—H8C	109.5	C18—C19—H19	119.7
C7—C9—H9A	109.5	C19—N1—C15	120.2 (3)
C7—C9—H9B	109.5	C19—N1—Co1	121.0 (3)
H9A—C9—H9B	109.5	C15—N1—Co1	118.7 (3)
C7—C9—H9C	109.5	C1—O1—Co1	109.7 (3)
H9A—C9—H9C	109.5	C2—O2—Co1	109.9 (2)
H9B—C9—H9C	109.5	O1—Co1—O1^i	180.00 (9)
C7—C10—H10A	109.5	O1—Co1—O2	87.18 (11)
C7—C10—H10B	109.5	O1^i—Co1—O2	92.82 (11)
H10A—C10—H10B	109.5	O1—Co1—O2^i	92.82 (11)
C7—C10—H10C	109.5	O1^i—Co1—O2^i	87.18 (11)
H10A—C10—H10C	109.5	O2—Co1—O2^i	180.0
H10B—C10—H10C	109.5	O1—Co1—N1	90.56 (13)
C13—C11—C14	109.5 (6)	O1^i—Co1—N1	89.44 (13)
C13—C11—C12	106.3 (5)	O2—Co1—N1	90.70 (12)
C14—C11—C12	109.2 (5)	O2^i—Co1—N1	89.30 (12)
C13—C11—C5	111.9 (4)	O1—Co1—N1^i	89.44 (13)
C14—C11—C5	109.4 (4)	O1^i—Co1—N1^i	90.56 (13)
C12—C11—C5	110.4 (4)	O2—Co1—N1^i	89.30 (12)
C11—C12—H12A	109.5	O2^i—Co1—N1^i	90.70 (12)
C11—C12—H12B	109.5	N1—Co1—N1^i	180.00 (13)
H12A—C12—H12B	109.5
O1—C1—C2—O2	−0.7 (5)	C6—C5—C11—C12	143.9 (5)
C6—C1—C2—O2	177.6 (3)	C4—C5—C11—C12	−36.0 (6)
O1—C1—C2—C3	179.6 (3)	N1—C15—C16—C17	1.8 (6)
C6—C1—C2—C3	−2.1 (5)	N1—C15—C16—Br2	−178.3 (3)
O2—C2—C3—C4	−178.7 (3)	C15—C16—C17—C18	0.8 (6)
C1—C2—C3—C4	1.0 (5)	Br2—C16—C17—C18	−179.1 (3)
O2—C2—C3—C7	−3.2 (5)	C16—C17—C18—C19	−3.1 (6)
C1—C2—C3—C7	176.4 (3)	C16—C17—C18—Br1	177.4 (3)
C2—C3—C4—C5	1.1 (6)	C17—C18—C19—N1	3.0 (6)
C7—C3—C4—C5	−174.3 (4)	Br1—C18—C19—N1	−177.5 (3)
C3—C4—C5—C6	−2.0 (6)	C18—C19—N1—C15	−0.3 (6)
C3—C4—C5—C11	177.9 (4)	C18—C19—N1—Co1	177.9 (3)
O1—C1—C6—C5	179.4 (3)	C16—C15—N1—C19	−2.1 (6)
C2—C1—C6—C5	1.2 (5)	C16—C15—N1—Co1	179.7 (3)
C4—C5—C6—C1	0.8 (5)	C6—C1—O1—Co1	177.4 (3)
C11—C5—C6—C1	−179.2 (3)	C2—C1—O1—Co1	−4.3 (4)
C4—C3—C7—C8	108.4 (4)	C1—C2—O2—Co1	5.3 (4)
C2—C3—C7—C8	−66.8 (5)	C3—C2—O2—Co1	−175.0 (3)
C4—C3—C7—C9	−131.9 (4)	C1—O1—Co1—O2	5.7 (2)
C2—C3—C7—C9	52.9 (5)	C1—O1—Co1—O2^i	−174.3 (2)
C4—C3—C7—C10	−10.8 (5)	C1—O1—Co1—N1	96.4 (2)
C2—C3—C7—C10	174.1 (3)	C1—O1—Co1—N1^i	−83.6 (2)
C6—C5—C11—C13	25.7 (6)	C2—O2—Co1—O1	−6.2 (2)
C4—C5—C11—C13	−154.2 (6)	C2—O2—Co1—O1^i	173.8 (2)
C6—C5—C11—C14	−95.8 (6)	C2—O2—Co1—N1	−96.7 (2)
C4—C5—C11—C14	84.2 (6)	C2—O2—Co1—N1^i	83.3 (2)

Symmetry code: (i) −x+1, −y+1, −z+2.

(1_200K)

Crystal data

C38H46Br4CoN2O4	Z = 1
Mr = 973.34	F(000) = 487
Triclinic, P1	Dx = 1.675 Mg m^−3
a = 8.9788 (11) Å	Ag Kα radiation, λ = 0.56085 Å
b = 10.1598 (13) Å	Cell parameters from 12572 reflections
c = 11.6606 (15) Å	θ = 1.4–19.5°
α = 86.014 (5)°	µ = 2.47 mm^−1
β = 89.423 (5)°	T = 200 K
γ = 65.463 (4)°	Block, blue
V = 965.1 (2) Å^3	0.20 × 0.17 × 0.14 mm

Data collection

Bruker Kappa APEX II CCD detector diffractometer	3104 independent reflections
Radiation source: Bruker, Kappa Apex II	2330 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.051
φ and ω scans	θmax = 19.5°, θmin = 1.4°
Absorption correction: multi-scan Bruker AXS, 2008	h = −10→10
Tmin = 0.610, Tmax = 0.707	k = −12→12
12572 measured reflections	l = −13→13

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.150	w = 1/[σ^2(Fo^2) + (0.0885P)^2 + 0.5627P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
3104 reflections	Δρmax = 0.86 e Å^−3
229 parameters	Δρmin = −0.98 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.4461 (7)	0.6144 (5)	0.2028 (4)	0.0221 (12)
C2	0.3149 (7)	0.5749 (5)	0.1846 (4)	0.0218 (12)
C3	0.1867 (7)	0.6075 (5)	0.2657 (4)	0.0265 (13)
C4	0.2023 (7)	0.6761 (6)	0.3618 (5)	0.0293 (14)
H4	0.1178	0.7001	0.4167	0.035*
C5	0.3332 (7)	0.7116 (6)	0.3828 (4)	0.0272 (13)
C6	0.4576 (7)	0.6808 (6)	0.3015 (4)	0.0270 (13)
H6	0.5478	0.7045	0.3133	0.032*
C7	0.0482 (7)	0.5607 (6)	0.2514 (5)	0.0315 (14)
C8	−0.0353 (8)	0.6078 (7)	0.1325 (5)	0.0387 (15)
H8A	−0.1326	0.5872	0.1312	0.058*
H8B	0.0410	0.5544	0.0741	0.058*
H8C	−0.0678	0.7121	0.1161	0.058*
C9	0.1156 (9)	0.3940 (7)	0.2655 (7)	0.0499 (19)
H9A	0.1640	0.3598	0.3428	0.075*
H9B	0.1994	0.3518	0.2081	0.075*
H9C	0.0262	0.3642	0.2547	0.075*
C10	−0.0850 (8)	0.6202 (7)	0.3429 (5)	0.0411 (16)
H10A	−0.0346	0.5892	0.4199	0.062*
H10B	−0.1682	0.5827	0.3334	0.062*
H10C	−0.1363	0.7265	0.3334	0.062*
C11	0.3421 (8)	0.7836 (6)	0.4935 (5)	0.0347 (15)
C12	0.2425 (14)	0.9445 (8)	0.4774 (7)	0.093 (4)
H12A	0.2544	0.9902	0.5460	0.139*
H12B	0.1270	0.9645	0.4656	0.139*
H12C	0.2810	0.9839	0.4102	0.139*
C13	0.5150 (12)	0.7491 (15)	0.5268 (8)	0.111 (5)
H13A	0.5511	0.8165	0.4837	0.167*
H13B	0.5853	0.6495	0.5092	0.167*
H13C	0.5221	0.7588	0.6094	0.167*
C14	0.2793 (16)	0.7199 (11)	0.5953 (6)	0.092 (4)
H14A	0.3102	0.7477	0.6671	0.138*
H14B	0.3277	0.6139	0.5949	0.138*
H14C	0.1598	0.7571	0.5893	0.138*
C15	0.2072 (7)	0.7399 (6)	−0.0861 (4)	0.0278 (13)
H15	0.1580	0.6742	−0.0694	0.033*
C16	0.1111 (7)	0.8803 (6)	−0.1304 (5)	0.0278 (13)
C17	0.1834 (7)	0.9731 (6)	−0.1579 (5)	0.0318 (14)
H17	0.1207	1.0681	−0.1913	0.038*
C18	0.3480 (8)	0.9265 (6)	−0.1362 (5)	0.0321 (14)
C19	0.4373 (7)	0.7865 (6)	−0.0886 (5)	0.0282 (13)
H19	0.5505	0.7552	−0.0715	0.034*
N1	0.3674 (5)	0.6957 (5)	−0.0668 (4)	0.0239 (10)
O1	0.5610 (5)	0.5809 (4)	0.1230 (3)	0.0243 (9)
O2	0.3200 (4)	0.5073 (4)	0.0892 (3)	0.0243 (9)
Co1	0.5000	0.5000	0.0000	0.0211 (3)
Br1	0.45283 (9)	1.04920 (7)	−0.16991 (7)	0.0549 (3)
Br2	−0.11540 (8)	0.94138 (7)	−0.15116 (6)	0.0426 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.019 (3)	0.021 (2)	0.024 (3)	−0.006 (2)	−0.003 (2)	0.0011 (19)
C2	0.018 (3)	0.020 (2)	0.026 (3)	−0.007 (2)	−0.003 (2)	0.002 (2)
C3	0.024 (3)	0.024 (3)	0.030 (3)	−0.009 (2)	−0.002 (2)	0.005 (2)
C4	0.026 (3)	0.033 (3)	0.027 (3)	−0.011 (3)	0.000 (2)	0.001 (2)
C5	0.021 (3)	0.027 (3)	0.031 (3)	−0.007 (2)	−0.004 (2)	0.000 (2)
C6	0.025 (3)	0.028 (3)	0.029 (3)	−0.012 (2)	−0.007 (2)	−0.001 (2)
C7	0.019 (3)	0.033 (3)	0.040 (3)	−0.009 (3)	−0.001 (3)	0.005 (2)
C8	0.026 (4)	0.048 (4)	0.046 (3)	−0.017 (3)	−0.001 (3)	−0.013 (3)
C9	0.037 (4)	0.038 (4)	0.078 (5)	−0.020 (3)	0.003 (4)	0.001 (3)
C10	0.024 (3)	0.058 (4)	0.044 (4)	−0.021 (3)	0.002 (3)	−0.003 (3)
C11	0.030 (4)	0.039 (3)	0.034 (3)	−0.013 (3)	−0.003 (3)	−0.006 (2)
C12	0.151 (11)	0.040 (4)	0.061 (5)	−0.011 (5)	−0.027 (6)	−0.021 (4)
C13	0.055 (6)	0.203 (13)	0.084 (7)	−0.049 (7)	0.009 (5)	−0.097 (8)
C14	0.173 (12)	0.120 (8)	0.038 (4)	−0.112 (8)	0.011 (6)	−0.020 (4)
C15	0.028 (3)	0.030 (3)	0.027 (3)	−0.014 (3)	−0.001 (3)	0.000 (2)
C16	0.021 (3)	0.032 (3)	0.030 (3)	−0.012 (3)	−0.004 (2)	−0.001 (2)
C17	0.027 (3)	0.029 (3)	0.036 (3)	−0.009 (3)	−0.003 (3)	0.002 (2)
C18	0.032 (4)	0.027 (3)	0.042 (3)	−0.017 (3)	0.004 (3)	−0.003 (2)
C19	0.018 (3)	0.030 (3)	0.037 (3)	−0.011 (2)	−0.003 (2)	0.002 (2)
N1	0.017 (2)	0.027 (2)	0.028 (2)	−0.0096 (19)	−0.0043 (19)	0.0010 (17)
O1	0.019 (2)	0.0284 (19)	0.0281 (19)	−0.0121 (16)	−0.0009 (16)	−0.0020 (14)
O2	0.018 (2)	0.0242 (18)	0.0306 (19)	−0.0087 (16)	−0.0021 (16)	−0.0025 (14)
Co1	0.0163 (6)	0.0220 (5)	0.0260 (5)	−0.0089 (4)	−0.0013 (4)	−0.0010 (4)
Br1	0.0338 (4)	0.0348 (4)	0.0986 (6)	−0.0204 (3)	−0.0118 (4)	0.0212 (3)
Br2	0.0226 (4)	0.0445 (4)	0.0575 (4)	−0.0113 (3)	−0.0130 (3)	0.0032 (3)

Geometric parameters (Å, º)

C1—O1	1.334 (6)	C11—C14	1.526 (10)
C1—C6	1.399 (8)	C15—N1	1.333 (7)
C1—C2	1.415 (8)	C15—C16	1.389 (7)
C2—O2	1.339 (7)	C16—C17	1.370 (9)
C2—C3	1.426 (7)	C16—Br2	1.876 (6)
C3—C4	1.399 (8)	C17—C18	1.371 (9)
C3—C7	1.519 (9)	C18—C19	1.388 (8)
C4—C5	1.393 (9)	C18—Br1	1.870 (6)
C5—C6	1.405 (7)	C19—N1	1.324 (7)
C5—C11	1.546 (8)	N1—Co1	1.953 (4)
C7—C8	1.531 (9)	O1—Co1	1.894 (4)
C7—C9	1.541 (8)	O2—Co1	1.891 (4)
C7—C10	1.549 (8)	Co1—O2^i	1.891 (4)
C11—C13	1.492 (12)	Co1—O1^i	1.894 (4)
C11—C12	1.501 (9)	Co1—N1^i	1.953 (4)
O1—C1—C6	121.7 (6)	C17—C16—Br2	120.7 (4)
O1—C1—C2	116.6 (5)	C15—C16—Br2	120.1 (5)
C6—C1—C2	121.7 (5)	C16—C17—C18	118.9 (5)
O2—C2—C1	116.4 (4)	C17—C18—C19	119.4 (6)
O2—C2—C3	123.5 (5)	C17—C18—Br1	120.8 (4)
C1—C2—C3	120.1 (5)	C19—C18—Br1	119.8 (5)
C4—C3—C2	116.0 (6)	N1—C19—C18	121.2 (6)
C4—C3—C7	122.5 (5)	C19—N1—C15	120.1 (5)
C2—C3—C7	121.4 (5)	C19—N1—Co1	119.2 (4)
C5—C4—C3	124.5 (5)	C15—N1—Co1	120.7 (4)
C4—C5—C6	118.9 (5)	C1—O1—Co1	109.7 (4)
C4—C5—C11	120.8 (5)	C2—O2—Co1	109.8 (4)
C6—C5—C11	120.3 (6)	O2^i—Co1—O2	180.0
C1—C6—C5	118.7 (6)	O2^i—Co1—O1^i	87.07 (16)
C3—C7—C8	112.7 (5)	O2—Co1—O1^i	92.93 (16)
C3—C7—C9	109.8 (5)	O2^i—Co1—O1	92.93 (16)
C8—C7—C9	107.0 (6)	O2—Co1—O1	87.07 (16)
C3—C7—C10	112.2 (5)	O1^i—Co1—O1	180.0
C8—C7—C10	108.0 (5)	O2^i—Co1—N1^i	89.52 (16)
C9—C7—C10	106.9 (5)	O2—Co1—N1^i	90.48 (16)
C13—C11—C12	111.1 (8)	O1^i—Co1—N1^i	89.33 (18)
C13—C11—C14	104.1 (8)	O1—Co1—N1^i	90.67 (18)
C12—C11—C14	110.1 (7)	O2^i—Co1—N1	90.48 (16)
C13—C11—C5	111.3 (5)	O2—Co1—N1	89.52 (16)
C12—C11—C5	109.9 (5)	O1^i—Co1—N1	90.67 (18)
C14—C11—C5	110.3 (6)	O1—Co1—N1	89.33 (18)
N1—C15—C16	121.1 (6)	N1^i—Co1—N1	180.0
C17—C16—C15	119.2 (6)
O1—C1—C2—O2	0.2 (6)	C4—C5—C11—C14	37.9 (9)
C6—C1—C2—O2	−177.6 (4)	C6—C5—C11—C14	−142.1 (7)
O1—C1—C2—C3	−179.7 (4)	N1—C15—C16—C17	2.0 (8)
C6—C1—C2—C3	2.5 (7)	N1—C15—C16—Br2	−177.5 (4)
O2—C2—C3—C4	178.8 (4)	C15—C16—C17—C18	−2.7 (8)
C1—C2—C3—C4	−1.3 (7)	Br2—C16—C17—C18	176.9 (4)
O2—C2—C3—C7	2.8 (7)	C16—C17—C18—C19	0.8 (8)
C1—C2—C3—C7	−177.2 (4)	C16—C17—C18—Br1	−179.1 (4)
C2—C3—C4—C5	−0.8 (8)	C17—C18—C19—N1	1.9 (8)
C7—C3—C4—C5	175.1 (5)	Br1—C18—C19—N1	−178.1 (4)
C3—C4—C5—C6	1.7 (8)	C18—C19—N1—C15	−2.7 (8)
C3—C4—C5—C11	−178.3 (5)	C18—C19—N1—Co1	179.9 (4)
O1—C1—C6—C5	−179.2 (4)	C16—C15—N1—C19	0.7 (8)
C2—C1—C6—C5	−1.5 (7)	C16—C15—N1—Co1	178.1 (4)
C4—C5—C6—C1	−0.5 (7)	C6—C1—O1—Co1	−177.8 (4)
C11—C5—C6—C1	179.5 (5)	C2—C1—O1—Co1	4.4 (5)
C4—C3—C7—C8	131.9 (5)	C1—C2—O2—Co1	−4.8 (5)
C2—C3—C7—C8	−52.4 (6)	C3—C2—O2—Co1	175.2 (4)
C4—C3—C7—C9	−109.0 (6)	C2—O2—Co1—O1^i	−174.3 (3)
C2—C3—C7—C9	66.7 (6)	C2—O2—Co1—O1	5.7 (3)
C4—C3—C7—C10	9.7 (7)	C2—O2—Co1—N1^i	96.4 (3)
C2—C3—C7—C10	−174.6 (5)	C2—O2—Co1—N1	−83.6 (3)
C4—C5—C11—C13	152.9 (8)	C1—O1—Co1—O2^i	174.4 (3)
C6—C5—C11—C13	−27.1 (9)	C1—O1—Co1—O2	−5.6 (3)
C4—C5—C11—C12	−83.6 (8)	C1—O1—Co1—N1^i	−96.1 (3)
C6—C5—C11—C12	96.5 (8)	C1—O1—Co1—N1	83.9 (3)

Symmetry code: (i) −x+1, −y+1, −z.

(1_235K)

Crystal data

C38H46Br4CoN2O4	Z = 1
Mr = 973.34	F(000) = 487
Triclinic, P1	Dx = 1.656 Mg m^−3
a = 9.0047 (11) Å	Ag Kα radiation, λ = 0.56085 Å
b = 10.2138 (12) Å	Cell parameters from 18550 reflections
c = 11.6756 (14) Å	θ = 1.4–20.5°
α = 86.394 (4)°	µ = 2.45 mm^−1
β = 89.775 (5)°	T = 235 K
γ = 65.652 (4)°	Block, blue
V = 976.1 (2) Å^3	0.20 × 0.17 × 0.14 mm

Data collection

Bruker Kappa APEX II CCD detector diffractometer	3840 independent reflections
Radiation source: Bruker, Kappa Apex II	2784 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.049
φ and ω scans	θmax = 20.5°, θmin = 1.4°
Absorption correction: multi-scan Bruker AXS, 2008	h = −11→10
Tmin = 0.640, Tmax = 0.726	k = −12→12
18550 measured reflections	l = −14→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.149	w = 1/[σ^2(Fo^2) + (0.084P)^2 + 0.2837P] where P = (Fo^2 + 2Fc^2)/3
S = 1.14	(Δ/σ)max < 0.001
3840 reflections	Δρmax = 1.26 e Å^−3
229 parameters	Δρmin = −0.99 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.9462 (5)	0.6147 (4)	0.7026 (3)	0.0265 (9)
C2	0.8149 (5)	0.5754 (4)	0.6844 (4)	0.0272 (9)
C3	0.6871 (6)	0.6077 (4)	0.7651 (4)	0.0320 (10)
C4	0.7033 (6)	0.6763 (5)	0.8608 (4)	0.0354 (11)
H4	0.6202	0.7005	0.9149	0.042*
C5	0.8354 (6)	0.7115 (5)	0.8817 (4)	0.0339 (10)
C6	0.9570 (6)	0.6815 (5)	0.8014 (4)	0.0328 (10)
H6	1.0456	0.7057	0.8132	0.039*
C7	0.5489 (6)	0.5605 (5)	0.7507 (4)	0.0379 (11)
C8	0.4643 (7)	0.6105 (6)	0.6328 (5)	0.0471 (13)
H8A	0.3680	0.5906	0.6306	0.071*
H8B	0.5385	0.5595	0.5741	0.071*
H8C	0.4328	0.7132	0.6188	0.071*
C9	0.6157 (8)	0.3958 (6)	0.7636 (6)	0.0628 (17)
H9A	0.6616	0.3620	0.8404	0.094*
H9B	0.6997	0.3549	0.7078	0.094*
H9C	0.5280	0.3662	0.7506	0.094*
C10	0.4167 (7)	0.6215 (7)	0.8414 (5)	0.0521 (14)
H10A	0.4652	0.5881	0.9176	0.078*
H10B	0.3312	0.5889	0.8297	0.078*
H10C	0.3709	0.7259	0.8337	0.078*
C11	0.8440 (7)	0.7825 (5)	0.9934 (4)	0.0417 (12)
C12	0.7848 (16)	0.7185 (11)	1.0935 (6)	0.120 (4)
H12A	0.8181	0.7440	1.1647	0.179*
H12B	0.8314	0.6145	1.0913	0.179*
H12C	0.6668	0.7556	1.0891	0.179*
C13	1.0179 (11)	0.7550 (14)	1.0246 (8)	0.131 (5)
H13A	1.0564	0.8086	0.9698	0.197*
H13B	1.0867	0.6529	1.0231	0.197*
H13C	1.0219	0.7858	1.1010	0.197*
C14	0.7440 (14)	0.9425 (8)	0.9776 (7)	0.120 (4)
H14A	0.7639	0.9888	1.0422	0.180*
H14B	0.6292	0.9618	0.9731	0.180*
H14C	0.7745	0.9799	0.9072	0.180*
C15	0.7082 (6)	0.7398 (5)	0.4135 (4)	0.0337 (10)
H15	0.6589	0.6758	0.4298	0.040*
C16	0.6138 (6)	0.8798 (5)	0.3690 (4)	0.0364 (11)
C17	0.6847 (6)	0.9723 (5)	0.3416 (4)	0.0385 (12)
H17	0.6232	1.0657	0.3088	0.046*
C18	0.8501 (6)	0.9241 (5)	0.3638 (4)	0.0386 (11)
C19	0.9385 (6)	0.7870 (5)	0.4109 (4)	0.0359 (11)
H19	1.0502	0.7566	0.4279	0.043*
N1	0.8681 (5)	0.6960 (4)	0.4330 (3)	0.0308 (8)
O1	1.0603 (4)	0.5815 (3)	0.6234 (2)	0.0293 (7)
O2	0.8199 (4)	0.5084 (3)	0.5896 (3)	0.0300 (7)
Co1	1.0000	0.5000	0.5000	0.0253 (2)
Br1	0.95517 (8)	1.04641 (6)	0.32996 (7)	0.0669 (2)
Br2	0.38695 (7)	0.94016 (6)	0.34839 (5)	0.0533 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.025 (2)	0.0266 (19)	0.027 (2)	−0.0093 (17)	−0.0039 (18)	−0.0005 (16)
C2	0.026 (2)	0.0235 (19)	0.032 (2)	−0.0102 (17)	−0.0004 (18)	0.0020 (16)
C3	0.029 (3)	0.030 (2)	0.037 (2)	−0.0123 (18)	−0.001 (2)	0.0013 (18)
C4	0.028 (3)	0.040 (2)	0.036 (2)	−0.0117 (19)	0.004 (2)	−0.0050 (19)
C5	0.036 (3)	0.030 (2)	0.035 (2)	−0.0133 (19)	−0.001 (2)	−0.0023 (18)
C6	0.029 (3)	0.036 (2)	0.035 (2)	−0.0161 (19)	−0.0075 (19)	−0.0009 (18)
C7	0.026 (3)	0.043 (3)	0.047 (3)	−0.016 (2)	0.002 (2)	0.000 (2)
C8	0.032 (3)	0.057 (3)	0.057 (3)	−0.022 (2)	0.003 (2)	−0.014 (2)
C9	0.048 (4)	0.048 (3)	0.101 (5)	−0.030 (3)	0.006 (3)	0.003 (3)
C10	0.034 (3)	0.076 (4)	0.053 (3)	−0.029 (3)	0.005 (3)	−0.008 (3)
C11	0.041 (3)	0.044 (3)	0.039 (3)	−0.016 (2)	−0.002 (2)	−0.008 (2)
C12	0.240 (13)	0.139 (8)	0.039 (4)	−0.136 (9)	0.014 (5)	−0.022 (4)
C13	0.066 (6)	0.238 (12)	0.097 (6)	−0.056 (7)	0.007 (5)	−0.112 (7)
C14	0.184 (11)	0.059 (5)	0.083 (5)	−0.013 (6)	−0.032 (6)	−0.037 (4)
C15	0.034 (3)	0.036 (2)	0.034 (2)	−0.019 (2)	−0.002 (2)	−0.0024 (18)
C16	0.034 (3)	0.041 (3)	0.035 (2)	−0.016 (2)	−0.004 (2)	−0.0020 (19)
C17	0.037 (3)	0.034 (2)	0.043 (3)	−0.014 (2)	−0.002 (2)	0.000 (2)
C18	0.039 (3)	0.032 (2)	0.049 (3)	−0.018 (2)	0.003 (2)	−0.005 (2)
C19	0.026 (2)	0.035 (2)	0.047 (3)	−0.0128 (19)	0.000 (2)	−0.0014 (19)
N1	0.027 (2)	0.0350 (19)	0.0339 (19)	−0.0155 (16)	0.0016 (16)	−0.0053 (15)
O1	0.0222 (16)	0.0358 (15)	0.0343 (16)	−0.0159 (12)	−0.0011 (13)	−0.0052 (12)
O2	0.0242 (16)	0.0306 (15)	0.0384 (16)	−0.0143 (12)	0.0000 (13)	−0.0050 (12)
Co1	0.0212 (4)	0.0262 (4)	0.0305 (4)	−0.0117 (3)	0.0004 (3)	−0.0029 (3)
Br1	0.0442 (4)	0.0422 (3)	0.1184 (6)	−0.0256 (3)	−0.0102 (3)	0.0220 (3)
Br2	0.0306 (3)	0.0561 (3)	0.0701 (4)	−0.0155 (2)	−0.0134 (3)	0.0023 (3)

Geometric parameters (Å, º)

C1—O1	1.330 (5)	C11—C13	1.514 (10)
C1—C6	1.401 (6)	C15—N1	1.335 (6)
C1—C2	1.417 (7)	C15—C16	1.394 (6)
C2—O2	1.329 (5)	C16—C17	1.364 (7)
C2—C3	1.428 (6)	C16—Br2	1.886 (5)
C3—C4	1.394 (7)	C17—C18	1.381 (7)
C3—C7	1.522 (7)	C18—C19	1.373 (6)
C4—C5	1.403 (7)	C18—Br1	1.877 (5)
C5—C6	1.387 (6)	C19—N1	1.337 (6)
C5—C11	1.550 (7)	N1—Co1	1.970 (4)
C7—C8	1.529 (8)	O1—Co1	1.896 (3)
C7—C9	1.532 (7)	O2—Co1	1.901 (3)
C7—C10	1.545 (6)	Co1—O1^i	1.896 (3)
C11—C12	1.505 (9)	Co1—O2^i	1.901 (3)
C11—C14	1.505 (8)	Co1—N1^i	1.970 (4)
O1—C1—C6	121.8 (4)	C17—C16—Br2	120.4 (4)
O1—C1—C2	117.0 (4)	C15—C16—Br2	119.3 (4)
C6—C1—C2	121.1 (4)	C16—C17—C18	117.7 (4)
O2—C2—C1	116.0 (3)	C19—C18—C17	120.4 (5)
O2—C2—C3	123.5 (4)	C19—C18—Br1	119.5 (4)
C1—C2—C3	120.5 (4)	C17—C18—Br1	120.0 (4)
C4—C3—C2	115.7 (4)	N1—C19—C18	120.9 (5)
C4—C3—C7	122.6 (4)	C15—N1—C19	120.0 (4)
C2—C3—C7	121.6 (4)	C15—N1—Co1	120.4 (3)
C3—C4—C5	124.4 (4)	C19—N1—Co1	119.5 (3)
C6—C5—C4	119.1 (4)	C1—O1—Co1	109.8 (3)
C6—C5—C11	120.9 (5)	C2—O2—Co1	110.3 (3)
C4—C5—C11	119.9 (4)	O1^i—Co1—O1	180.00 (17)
C5—C6—C1	119.1 (5)	O1^i—Co1—O2	93.45 (13)
C3—C7—C8	111.8 (4)	O1—Co1—O2	86.54 (13)
C3—C7—C9	109.9 (4)	O1^i—Co1—O2^i	86.54 (13)
C8—C7—C9	108.0 (5)	O1—Co1—O2^i	93.46 (13)
C3—C7—C10	111.9 (4)	O2—Co1—O2^i	180.0
C8—C7—C10	107.1 (4)	O1^i—Co1—N1	91.00 (14)
C9—C7—C10	108.0 (4)	O1—Co1—N1	89.00 (14)
C12—C11—C14	110.6 (7)	O2—Co1—N1	89.60 (13)
C12—C11—C13	105.6 (7)	O2^i—Co1—N1	90.40 (13)
C14—C11—C13	108.9 (8)	O1^i—Co1—N1^i	89.00 (14)
C12—C11—C5	110.7 (5)	O1—Co1—N1^i	91.00 (14)
C14—C11—C5	109.5 (5)	O2—Co1—N1^i	90.40 (13)
C13—C11—C5	111.4 (4)	O2^i—Co1—N1^i	89.60 (13)
N1—C15—C16	120.5 (5)	N1—Co1—N1^i	180.0
C17—C16—C15	120.3 (5)
O1—C1—C2—O2	0.3 (5)	C6—C5—C11—C14	96.6 (7)
C6—C1—C2—O2	−177.8 (4)	C4—C5—C11—C14	−83.5 (7)
O1—C1—C2—C3	−179.7 (3)	C6—C5—C11—C13	−23.9 (8)
C6—C1—C2—C3	2.2 (6)	C4—C5—C11—C13	155.9 (7)
O2—C2—C3—C4	178.9 (4)	N1—C15—C16—C17	2.0 (7)
C1—C2—C3—C4	−1.1 (6)	N1—C15—C16—Br2	−177.5 (3)
O2—C2—C3—C7	3.0 (6)	C15—C16—C17—C18	−2.5 (7)
C1—C2—C3—C7	−177.0 (4)	Br2—C16—C17—C18	176.9 (4)
C2—C3—C4—C5	−1.0 (6)	C16—C17—C18—C19	0.6 (7)
C7—C3—C4—C5	174.8 (4)	C16—C17—C18—Br1	−179.3 (3)
C3—C4—C5—C6	2.2 (7)	C17—C18—C19—N1	2.1 (7)
C3—C4—C5—C11	−177.7 (4)	Br1—C18—C19—N1	−178.1 (3)
C4—C5—C6—C1	−1.1 (6)	C16—C15—N1—C19	0.6 (6)
C11—C5—C6—C1	178.8 (4)	C16—C15—N1—Co1	178.2 (3)
O1—C1—C6—C5	−179.0 (4)	C18—C19—N1—C15	−2.6 (7)
C2—C1—C6—C5	−1.0 (6)	C18—C19—N1—Co1	179.8 (3)
C4—C3—C7—C8	130.5 (5)	C6—C1—O1—Co1	−177.7 (3)
C2—C3—C7—C8	−53.9 (5)	C2—C1—O1—Co1	4.3 (4)
C4—C3—C7—C9	−109.6 (5)	C1—C2—O2—Co1	−4.6 (4)
C2—C3—C7—C9	66.0 (6)	C3—C2—O2—Co1	175.3 (3)
C4—C3—C7—C10	10.4 (6)	C1—O1—Co1—O2	−5.4 (3)
C2—C3—C7—C10	−174.1 (4)	C1—O1—Co1—O2^i	174.6 (3)
C6—C5—C11—C12	−141.2 (7)	C1—O1—Co1—N1	84.3 (3)
C4—C5—C11—C12	38.7 (8)	C1—O1—Co1—N1^i	−95.7 (3)

Symmetry code: (i) −x+2, −y+1, −z+1.

(1_250K)

Crystal data

C38H46Br4CoN2O4	Z = 1
Mr = 973.34	F(000) = 487
Triclinic, P1	Dx = 1.619 Mg m^−3
a = 8.9569 (9) Å	Ag Kα radiation, λ = 0.56085 Å
b = 10.7763 (10) Å	Cell parameters from 19168 reflections
c = 11.7042 (12) Å	θ = 1.4–20.6°
α = 85.308 (4)°	µ = 2.39 mm^−1
β = 87.784 (4)°	T = 250 K
γ = 62.483 (3)°	Block, blue
V = 998.56 (17) Å^3	0.20 × 0.17 × 0.14 mm

Data collection

Bruker Kappa APEX II CCD detector diffractometer	3924 independent reflections
Radiation source: Bruker, Kappa Apex II	2714 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.048
φ and ω scans	θmax = 20.7°, θmin = 1.4°
Absorption correction: multi-scan Bruker AXS, 2008	h = −11→10
Tmin = 0.646, Tmax = 0.731	k = −13→13
19168 measured reflections	l = −14→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.162	w = 1/[σ^2(Fo^2) + (0.0937P)^2 + 0.1567P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
3924 reflections	Δρmax = 0.91 e Å^−3
229 parameters	Δρmin = −0.93 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	−0.0586 (6)	0.1142 (4)	0.7097 (4)	0.0319 (10)
C2	0.1170 (6)	0.0732 (4)	0.6866 (4)	0.0311 (10)
C3	0.2126 (6)	0.1043 (4)	0.7648 (4)	0.0364 (11)
C4	0.1280 (7)	0.1717 (5)	0.8613 (4)	0.0412 (12)
H4	0.1882	0.1943	0.9128	0.049*
C5	−0.0424 (7)	0.2087 (5)	0.8873 (4)	0.0375 (11)
C6	−0.1351 (6)	0.1808 (5)	0.8103 (4)	0.0383 (11)
H6	−0.2491	0.2062	0.8252	0.046*
C7	0.3998 (7)	0.0585 (5)	0.7449 (4)	0.0433 (12)
C8	0.4290 (7)	0.1166 (6)	0.6279 (4)	0.0488 (13)
H8A	0.3580	0.2173	0.6200	0.073*
H8B	0.4014	0.0732	0.5682	0.073*
H8C	0.5462	0.0964	0.6208	0.073*
C9	0.4963 (8)	−0.1007 (6)	0.7521 (6)	0.0690 (18)
H9A	0.6150	−0.1296	0.7388	0.103*
H9B	0.4542	−0.1364	0.6944	0.103*
H9C	0.4812	−0.1377	0.8276	0.103*
C10	0.4740 (8)	0.1103 (7)	0.8357 (5)	0.0630 (16)
H10A	0.4134	0.2118	0.8341	0.094*
H10B	0.5920	0.0812	0.8190	0.094*
H10C	0.4633	0.0705	0.9110	0.094*
C11	−0.1208 (8)	0.2776 (5)	0.9984 (4)	0.0481 (13)
C12	0.0022 (12)	0.2092 (10)	1.0967 (6)	0.120 (4)
H12A	0.0977	0.2279	1.0837	0.180*
H12B	0.0407	0.1088	1.1017	0.180*
H12C	−0.0531	0.2472	1.1678	0.180*
C13	−0.2763 (16)	0.2652 (16)	1.0320 (8)	0.154 (6)
H13A	−0.3090	0.2943	1.1091	0.232*
H13B	−0.2544	0.1685	1.0293	0.232*
H13C	−0.3666	0.3247	0.9792	0.232*
C14	−0.1680 (15)	0.4301 (8)	0.9828 (7)	0.130 (5)
H14A	−0.2205	0.4748	1.0524	0.195*
H14B	−0.2464	0.4732	0.9195	0.195*
H14C	−0.0678	0.4414	0.9665	0.195*
C15	0.0466 (7)	0.2546 (5)	0.4111 (4)	0.0416 (12)
H15	0.1596	0.1936	0.4298	0.050*
C16	0.0046 (7)	0.3891 (5)	0.3669 (4)	0.0417 (11)
C17	−0.1574 (7)	0.4783 (5)	0.3380 (4)	0.0468 (13)
H17	−0.1877	0.5695	0.3057	0.056*
C18	−0.2762 (7)	0.4316 (5)	0.3575 (5)	0.0456 (12)
C19	−0.2279 (7)	0.2969 (5)	0.4030 (4)	0.0449 (12)
H19	−0.3101	0.2663	0.4168	0.054*
N1	−0.0672 (5)	0.2083 (4)	0.4282 (3)	0.0373 (9)
O1	−0.1415 (4)	0.0852 (3)	0.6373 (3)	0.0380 (7)
O2	0.1789 (4)	0.0091 (3)	0.5955 (3)	0.0349 (7)
Co1	0.0000	0.0000	0.5000	0.0303 (2)
Br1	−0.50290 (9)	0.55032 (6)	0.32259 (8)	0.0818 (3)
Br2	0.17243 (8)	0.44837 (6)	0.34859 (5)	0.0634 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.031 (3)	0.032 (2)	0.034 (2)	−0.0164 (19)	0.0014 (19)	0.0015 (17)
C2	0.028 (3)	0.028 (2)	0.034 (2)	−0.0105 (18)	0.0002 (19)	0.0024 (16)
C3	0.033 (3)	0.037 (2)	0.041 (2)	−0.018 (2)	−0.003 (2)	0.0023 (18)
C4	0.043 (3)	0.050 (3)	0.037 (2)	−0.026 (2)	−0.002 (2)	−0.005 (2)
C5	0.039 (3)	0.038 (2)	0.037 (2)	−0.019 (2)	0.004 (2)	−0.0041 (18)
C6	0.031 (3)	0.040 (2)	0.042 (3)	−0.015 (2)	0.006 (2)	−0.0037 (19)
C7	0.032 (3)	0.049 (3)	0.052 (3)	−0.022 (2)	−0.004 (2)	0.002 (2)
C8	0.039 (3)	0.056 (3)	0.057 (3)	−0.026 (2)	0.008 (2)	−0.010 (2)
C9	0.034 (4)	0.058 (3)	0.105 (5)	−0.014 (3)	0.001 (3)	0.004 (3)
C10	0.050 (4)	0.092 (4)	0.062 (4)	−0.046 (3)	−0.008 (3)	0.002 (3)
C11	0.054 (4)	0.052 (3)	0.040 (3)	−0.026 (3)	0.010 (2)	−0.011 (2)
C12	0.118 (8)	0.117 (7)	0.049 (4)	0.014 (6)	−0.010 (4)	−0.020 (4)
C13	0.158 (11)	0.290 (15)	0.104 (7)	−0.169 (12)	0.096 (7)	−0.122 (9)
C14	0.223 (13)	0.063 (5)	0.085 (5)	−0.050 (6)	0.051 (7)	−0.035 (4)
C15	0.038 (3)	0.047 (3)	0.036 (2)	−0.017 (2)	0.002 (2)	−0.002 (2)
C16	0.042 (3)	0.049 (3)	0.036 (2)	−0.023 (2)	0.004 (2)	−0.001 (2)
C17	0.045 (3)	0.044 (3)	0.050 (3)	−0.019 (2)	0.001 (3)	−0.006 (2)
C18	0.035 (3)	0.040 (2)	0.059 (3)	−0.015 (2)	−0.001 (2)	−0.003 (2)
C19	0.037 (3)	0.049 (3)	0.051 (3)	−0.022 (2)	0.001 (2)	−0.004 (2)
N1	0.035 (2)	0.042 (2)	0.036 (2)	−0.0184 (18)	0.0043 (17)	−0.0037 (16)
O1	0.0261 (19)	0.0485 (17)	0.0423 (17)	−0.0196 (14)	0.0033 (14)	−0.0057 (14)
O2	0.0269 (18)	0.0373 (15)	0.0410 (17)	−0.0152 (13)	0.0051 (14)	−0.0060 (13)
Co1	0.0274 (5)	0.0326 (4)	0.0321 (4)	−0.0146 (4)	0.0021 (3)	−0.0041 (3)
Br1	0.0380 (4)	0.0537 (4)	0.1430 (7)	−0.0154 (3)	−0.0124 (4)	0.0203 (4)
Br2	0.0536 (4)	0.0705 (4)	0.0777 (4)	−0.0405 (3)	0.0077 (3)	0.0045 (3)

Geometric parameters (Å, º)

C1—O1	1.293 (5)	C11—C12	1.514 (9)
C1—C6	1.412 (6)	C15—N1	1.329 (6)
C1—C2	1.445 (7)	C15—C16	1.378 (7)
C2—O2	1.282 (5)	C16—C17	1.356 (7)
C2—C3	1.435 (6)	C16—Br2	1.885 (5)
C3—C4	1.391 (7)	C17—C18	1.377 (8)
C3—C7	1.527 (7)	C18—C19	1.374 (7)
C4—C5	1.415 (7)	C18—Br1	1.872 (5)
C5—C6	1.388 (6)	C19—N1	1.337 (6)
C5—C11	1.529 (7)	N1—Co1	2.142 (4)
C7—C9	1.519 (7)	O1—Co1	2.010 (3)
C7—C8	1.523 (7)	O2—Co1	2.032 (3)
C7—C10	1.542 (7)	Co1—O1^i	2.010 (3)
C11—C14	1.492 (9)	Co1—O2^i	2.032 (3)
C11—C13	1.495 (11)	Co1—N1^i	2.142 (4)
O1—C1—C6	121.4 (4)	C17—C16—Br2	120.5 (4)
O1—C1—C2	118.2 (4)	C15—C16—Br2	119.7 (4)
C6—C1—C2	120.4 (4)	C16—C17—C18	118.2 (5)
O2—C2—C3	123.6 (4)	C19—C18—C17	119.7 (5)
O2—C2—C1	116.7 (4)	C19—C18—Br1	119.8 (4)
C3—C2—C1	119.7 (4)	C17—C18—Br1	120.5 (4)
C4—C3—C2	116.6 (4)	N1—C19—C18	121.8 (5)
C4—C3—C7	122.3 (4)	C15—N1—C19	118.3 (4)
C2—C3—C7	121.0 (4)	C15—N1—Co1	121.7 (3)
C3—C4—C5	124.6 (4)	C19—N1—Co1	120.0 (4)
C6—C5—C4	118.5 (4)	C1—O1—Co1	111.4 (3)
C6—C5—C11	121.3 (5)	C2—O2—Co1	111.9 (3)
C4—C5—C11	120.1 (4)	O1—Co1—O1^i	180.0
C5—C6—C1	120.2 (5)	O1—Co1—O2^i	98.73 (12)
C9—C7—C8	109.4 (5)	O1^i—Co1—O2^i	81.27 (12)
C9—C7—C3	109.6 (4)	O1—Co1—O2	81.27 (12)
C8—C7—C3	110.8 (4)	O1^i—Co1—O2	98.73 (12)
C9—C7—C10	107.5 (5)	O2^i—Co1—O2	180.0
C8—C7—C10	107.4 (4)	O1—Co1—N1^i	91.85 (14)
C3—C7—C10	112.0 (4)	O1^i—Co1—N1^i	88.15 (14)
C14—C11—C13	107.7 (8)	O2^i—Co1—N1^i	89.06 (13)
C14—C11—C12	109.9 (6)	O2—Co1—N1^i	90.94 (13)
C13—C11—C12	106.9 (8)	O1—Co1—N1	88.15 (14)
C14—C11—C5	109.2 (5)	O1^i—Co1—N1	91.85 (14)
C13—C11—C5	112.7 (5)	O2^i—Co1—N1	90.94 (13)
C12—C11—C5	110.4 (5)	O2—Co1—N1	89.06 (13)
N1—C15—C16	122.3 (5)	N1^i—Co1—N1	180.0
C17—C16—C15	119.7 (5)
O1—C1—C2—O2	−0.7 (5)	C6—C5—C11—C14	−100.1 (7)
C6—C1—C2—O2	177.8 (4)	C4—C5—C11—C14	80.0 (7)
O1—C1—C2—C3	179.7 (4)	C6—C5—C11—C13	19.4 (9)
C6—C1—C2—C3	−1.9 (6)	C4—C5—C11—C13	−160.4 (8)
O2—C2—C3—C4	−178.6 (4)	C6—C5—C11—C12	139.0 (7)
C1—C2—C3—C4	1.0 (6)	C4—C5—C11—C12	−40.9 (8)
O2—C2—C3—C7	−1.5 (6)	N1—C15—C16—C17	−0.8 (7)
C1—C2—C3—C7	178.1 (4)	N1—C15—C16—Br2	178.5 (3)
C2—C3—C4—C5	1.0 (7)	C15—C16—C17—C18	1.9 (7)
C7—C3—C4—C5	−176.0 (4)	Br2—C16—C17—C18	−177.4 (4)
C3—C4—C5—C6	−2.2 (7)	C16—C17—C18—C19	−1.2 (8)
C3—C4—C5—C11	177.6 (4)	C16—C17—C18—Br1	178.7 (4)
C4—C5—C6—C1	1.3 (6)	C17—C18—C19—N1	−0.7 (8)
C11—C5—C6—C1	−178.5 (4)	Br1—C18—C19—N1	179.4 (4)
O1—C1—C6—C5	179.1 (4)	C16—C15—N1—C19	−1.1 (7)
C2—C1—C6—C5	0.7 (6)	C16—C15—N1—Co1	−178.8 (3)
C4—C3—C7—C9	112.9 (5)	C18—C19—N1—C15	1.8 (7)
C2—C3—C7—C9	−64.0 (6)	C18—C19—N1—Co1	179.6 (4)
C4—C3—C7—C8	−126.2 (5)	C6—C1—O1—Co1	177.1 (3)
C2—C3—C7—C8	56.8 (5)	C2—C1—O1—Co1	−4.5 (4)
C4—C3—C7—C10	−6.3 (6)	C3—C2—O2—Co1	−174.9 (3)
C2—C3—C7—C10	176.8 (4)	C1—C2—O2—Co1	5.5 (4)

Symmetry code: (i) −x, −y, −z+1.

(1_296K)

Crystal data

C38H46Br4CoN2O4	Z = 1
Mr = 973.34	F(000) = 487
Triclinic, P1	Dx = 1.583 Mg m^−3
a = 9.0080 (18) Å	Ag Kα radiation, λ = 0.56085 Å
b = 10.899 (2) Å	Cell parameters from 10682 reflections
c = 11.769 (2) Å	θ = 1.7–20.8°
α = 85.328 (6)°	µ = 2.34 mm^−1
β = 87.483 (6)°	T = 296 K
γ = 62.462 (5)°	Block, blue
V = 1021.2 (4) Å^3	0.20 × 0.17 × 0.14 mm

Data collection

Bruker Kappa APEX II CCD detector diffractometer	4343 independent reflections
Radiation source: Bruker, Kappa Apex II	2492 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.051
φ and ω scans	θmax = 20.9°, θmin = 1.7°
Absorption correction: multi-scan Bruker AXS, 2008	h = −11→9
Tmin = 0.652, Tmax = 0.735	k = −13→13
10682 measured reflections	l = −14→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.061	H-atom parameters constrained
wR(F^2) = 0.175	w = 1/[σ^2(Fo^2) + (0.0942P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.001
4343 reflections	Δρmax = 1.39 e Å^−3
229 parameters	Δρmin = −0.66 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Br1	1.50267 (9)	0.45148 (7)	0.67736 (8)	0.0944 (3)
Br2	0.82897 (9)	0.55237 (7)	0.65176 (6)	0.0759 (3)
C1	1.0602 (6)	0.8855 (5)	0.2902 (4)	0.0355 (11)
C2	0.8827 (6)	0.9267 (5)	0.3128 (4)	0.0355 (11)
C3	0.7891 (6)	0.8951 (5)	0.2356 (4)	0.0414 (12)
C4	0.8722 (7)	0.8294 (5)	0.1395 (4)	0.0469 (13)
H4	0.8125	0.8085	0.0886	0.056*
C5	1.0435 (7)	0.7917 (5)	0.1136 (4)	0.0434 (12)
C6	1.1348 (6)	0.8186 (5)	0.1893 (4)	0.0430 (12)
H6	1.2472	0.7926	0.1742	0.052*
C7	0.6013 (6)	0.9399 (6)	0.2555 (5)	0.0480 (13)
C8	0.5731 (7)	0.8815 (6)	0.3715 (5)	0.0576 (15)
H8A	0.5986	0.9248	0.4304	0.086*
H8B	0.6447	0.7833	0.3789	0.086*
H8C	0.4583	0.8996	0.3786	0.086*
C9	0.5058 (8)	1.0996 (7)	0.2505 (7)	0.077 (2)
H9A	0.3890	1.1286	0.2653	0.116*
H9B	0.5194	1.1366	0.1761	0.116*
H9C	0.5494	1.1330	0.3068	0.116*
C10	0.5271 (8)	0.8897 (8)	0.1647 (6)	0.075 (2)
H10A	0.4121	0.9151	0.1831	0.112*
H10B	0.5893	0.7907	0.1633	0.112*
H10C	0.5338	0.9320	0.0912	0.112*
C11	1.1192 (8)	0.7230 (6)	0.0014 (5)	0.0529 (14)
C12	1.0031 (13)	0.7940 (11)	−0.0956 (7)	0.142 (5)
H12A	0.9232	0.7589	−0.0971	0.213*
H12B	1.0657	0.7770	−0.1657	0.213*
H12C	0.9454	0.8919	−0.0866	0.213*
C13	1.2802 (15)	0.7294 (15)	−0.0287 (9)	0.168 (6)
H13A	1.2595	0.8244	−0.0344	0.252*
H13B	1.3219	0.6897	−0.1004	0.252*
H13C	1.3615	0.6784	0.0296	0.252*
C14	1.1621 (15)	0.5735 (8)	0.0154 (8)	0.145 (5)
H14A	1.2432	0.5286	0.0749	0.218*
H14B	1.2079	0.5311	−0.0548	0.218*
H14C	1.0630	0.5643	0.0351	0.218*
C15	0.9562 (7)	0.7440 (6)	0.5903 (4)	0.0477 (13)
H15	0.8448	0.8040	0.5732	0.057*
C16	0.9977 (7)	0.6105 (6)	0.6331 (4)	0.0483 (13)
C17	1.1591 (7)	0.5217 (6)	0.6614 (5)	0.0527 (14)
H17	1.1892	0.4320	0.6921	0.063*
C18	1.2762 (7)	0.5693 (5)	0.6432 (5)	0.0535 (14)
C19	1.2285 (6)	0.7030 (5)	0.5982 (5)	0.0481 (13)
H19	1.3093	0.7331	0.5853	0.058*
Co1	1.0000	1.0000	0.5000	0.0360 (3)
N1	1.0689 (5)	0.7905 (4)	0.5727 (3)	0.0427 (10)
O1	1.1410 (4)	0.9138 (4)	0.3607 (3)	0.0434 (8)
O2	0.8204 (4)	0.9904 (3)	0.4035 (3)	0.0393 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0469 (4)	0.0627 (5)	0.1601 (8)	−0.0181 (3)	−0.0142 (4)	0.0275 (4)
Br2	0.0666 (5)	0.0808 (5)	0.0955 (6)	−0.0494 (4)	0.0126 (4)	0.0040 (4)
C1	0.036 (3)	0.037 (3)	0.038 (3)	−0.020 (2)	0.004 (2)	−0.001 (2)
C2	0.038 (3)	0.037 (3)	0.033 (3)	−0.018 (2)	0.004 (2)	−0.002 (2)
C3	0.037 (3)	0.043 (3)	0.045 (3)	−0.020 (2)	0.000 (2)	0.001 (2)
C4	0.051 (3)	0.059 (4)	0.043 (3)	−0.035 (3)	−0.002 (3)	−0.010 (3)
C5	0.047 (3)	0.041 (3)	0.045 (3)	−0.022 (2)	0.006 (2)	−0.009 (2)
C6	0.036 (3)	0.045 (3)	0.046 (3)	−0.018 (2)	0.009 (2)	−0.005 (2)
C7	0.033 (3)	0.060 (4)	0.055 (3)	−0.026 (3)	−0.002 (3)	0.002 (3)
C8	0.048 (3)	0.069 (4)	0.065 (4)	−0.035 (3)	0.009 (3)	−0.012 (3)
C9	0.043 (4)	0.069 (4)	0.117 (6)	−0.025 (3)	0.000 (4)	0.004 (4)
C10	0.057 (4)	0.123 (6)	0.067 (4)	−0.060 (4)	−0.009 (3)	−0.001 (4)
C11	0.063 (4)	0.058 (4)	0.038 (3)	−0.027 (3)	0.013 (3)	−0.015 (3)
C12	0.146 (9)	0.156 (9)	0.048 (5)	−0.002 (7)	−0.004 (5)	−0.028 (5)
C13	0.177 (11)	0.286 (15)	0.115 (8)	−0.162 (11)	0.109 (8)	−0.126 (9)
C14	0.252 (14)	0.063 (5)	0.099 (7)	−0.053 (7)	0.056 (8)	−0.039 (5)
C15	0.040 (3)	0.055 (4)	0.044 (3)	−0.020 (3)	0.001 (2)	0.002 (3)
C16	0.049 (3)	0.057 (4)	0.043 (3)	−0.029 (3)	0.004 (3)	0.001 (3)
C17	0.053 (4)	0.045 (3)	0.057 (4)	−0.021 (3)	0.007 (3)	−0.005 (3)
C18	0.039 (3)	0.041 (3)	0.071 (4)	−0.011 (2)	0.000 (3)	−0.005 (3)
C19	0.043 (3)	0.048 (3)	0.057 (4)	−0.024 (3)	0.002 (3)	−0.003 (3)
Co1	0.0342 (5)	0.0392 (6)	0.0371 (5)	−0.0187 (4)	0.0033 (4)	−0.0062 (4)
N1	0.042 (2)	0.044 (3)	0.043 (2)	−0.021 (2)	0.0044 (19)	0.0002 (19)
O1	0.0321 (18)	0.058 (2)	0.046 (2)	−0.0253 (17)	0.0047 (16)	−0.0098 (17)
O2	0.0303 (17)	0.047 (2)	0.044 (2)	−0.0204 (15)	0.0074 (15)	−0.0079 (16)

Geometric parameters (Å, º)

Br1—C18	1.881 (5)	C11—C14	1.487 (9)
Br2—C16	1.897 (6)	C11—C13	1.509 (11)
C1—O1	1.271 (5)	C12—H12A	0.9600
C1—C6	1.417 (7)	C12—H12B	0.9600
C1—C2	1.466 (7)	C12—H12C	0.9600
C2—O2	1.283 (5)	C13—H13A	0.9600
C2—C3	1.429 (7)	C13—H13B	0.9600
C3—C4	1.383 (7)	C13—H13C	0.9600
C3—C7	1.541 (7)	C14—H14A	0.9600
C4—C5	1.427 (7)	C14—H14B	0.9600
C4—H4	0.9300	C14—H14C	0.9600
C5—C6	1.374 (7)	C15—N1	1.331 (6)
C5—C11	1.543 (7)	C15—C16	1.379 (7)
C6—H6	0.9300	C15—H15	0.9300
C7—C8	1.520 (8)	C16—C17	1.360 (7)
C7—C9	1.541 (8)	C17—C18	1.377 (8)
C7—C10	1.545 (8)	C17—H17	0.9300
C8—H8A	0.9600	C18—C19	1.380 (8)
C8—H8B	0.9600	C19—N1	1.338 (6)
C8—H8C	0.9600	C19—H19	0.9300
C9—H9A	0.9600	Co1—O1^i	2.036 (3)
C9—H9B	0.9600	Co1—O1	2.036 (3)
C9—H9C	0.9600	Co1—O2^i	2.062 (3)
C10—H10A	0.9600	Co1—O2	2.062 (3)
C10—H10B	0.9600	Co1—N1	2.179 (4)
C10—H10C	0.9600	Co1—N1^i	2.179 (4)
C11—C12	1.485 (10)
O1—C1—C6	122.3 (4)	C11—C12—H12C	109.5
O1—C1—C2	118.6 (4)	H12A—C12—H12C	109.5
C6—C1—C2	119.0 (4)	H12B—C12—H12C	109.5
O2—C2—C3	123.7 (4)	C11—C13—H13A	109.5
O2—C2—C1	116.4 (4)	C11—C13—H13B	109.5
C3—C2—C1	119.9 (4)	H13A—C13—H13B	109.5
C4—C3—C2	117.1 (5)	C11—C13—H13C	109.5
C4—C3—C7	121.7 (5)	H13A—C13—H13C	109.5
C2—C3—C7	121.2 (4)	H13B—C13—H13C	109.5
C3—C4—C5	124.2 (5)	C11—C14—H14A	109.5
C3—C4—H4	117.9	C11—C14—H14B	109.5
C5—C4—H4	117.9	H14A—C14—H14B	109.5
C6—C5—C4	118.7 (5)	C11—C14—H14C	109.5
C6—C5—C11	122.4 (5)	H14A—C14—H14C	109.5
C4—C5—C11	118.9 (5)	H14B—C14—H14C	109.5
C5—C6—C1	121.0 (5)	N1—C15—C16	122.7 (5)
C5—C6—H6	119.5	N1—C15—H15	118.6
C1—C6—H6	119.5	C16—C15—H15	118.6
C8—C7—C9	109.3 (5)	C17—C16—C15	119.8 (5)
C8—C7—C3	110.4 (4)	C17—C16—Br2	120.5 (4)
C9—C7—C3	108.8 (4)	C15—C16—Br2	119.7 (4)
C8—C7—C10	107.7 (5)	C16—C17—C18	117.6 (5)
C9—C7—C10	108.1 (5)	C16—C17—H17	121.2
C3—C7—C10	112.5 (5)	C18—C17—H17	121.2
C7—C8—H8A	109.5	C17—C18—C19	120.2 (5)
C7—C8—H8B	109.5	C17—C18—Br1	120.2 (4)
H8A—C8—H8B	109.5	C19—C18—Br1	119.7 (4)
C7—C8—H8C	109.5	N1—C19—C18	121.8 (5)
H8A—C8—H8C	109.5	N1—C19—H19	119.1
H8B—C8—H8C	109.5	C18—C19—H19	119.1
C7—C9—H9A	109.5	O1^i—Co1—O1	180.00 (11)
C7—C9—H9B	109.5	O1^i—Co1—O2^i	80.40 (12)
H9A—C9—H9B	109.5	O1—Co1—O2^i	99.60 (13)
C7—C9—H9C	109.5	O1^i—Co1—O2	99.60 (13)
H9A—C9—H9C	109.5	O1—Co1—O2	80.40 (12)
H9B—C9—H9C	109.5	O2^i—Co1—O2	180.0
C7—C10—H10A	109.5	O1^i—Co1—N1	92.11 (15)
C7—C10—H10B	109.5	O1—Co1—N1	87.89 (15)
H10A—C10—H10B	109.5	O2^i—Co1—N1	90.67 (14)
C7—C10—H10C	109.5	O2—Co1—N1	89.33 (14)
H10A—C10—H10C	109.5	O1^i—Co1—N1^i	87.89 (15)
H10B—C10—H10C	109.5	O1—Co1—N1^i	92.11 (15)
C12—C11—C14	111.0 (7)	O2^i—Co1—N1^i	89.33 (14)
C12—C11—C13	107.1 (8)	O2—Co1—N1^i	90.67 (14)
C14—C11—C13	106.6 (7)	N1—Co1—N1^i	180.0
C12—C11—C5	111.3 (5)	C15—N1—C19	117.8 (5)
C14—C11—C5	109.5 (5)	C15—N1—Co1	121.7 (4)
C13—C11—C5	111.2 (5)	C19—N1—Co1	120.4 (4)
C11—C12—H12A	109.5	C1—O1—Co1	112.1 (3)
C11—C12—H12B	109.5	C2—O2—Co1	112.0 (3)
H12A—C12—H12B	109.5
O1—C1—C2—O2	0.5 (6)	C6—C5—C11—C12	−135.9 (8)
C6—C1—C2—O2	−178.0 (4)	C4—C5—C11—C12	43.7 (9)
O1—C1—C2—C3	−179.4 (4)	C6—C5—C11—C14	100.9 (7)
C6—C1—C2—C3	2.1 (7)	C4—C5—C11—C14	−79.4 (8)
O2—C2—C3—C4	178.1 (5)	C6—C5—C11—C13	−16.6 (9)
C1—C2—C3—C4	−1.9 (7)	C4—C5—C11—C13	163.0 (8)
O2—C2—C3—C7	1.5 (7)	N1—C15—C16—C17	1.6 (8)
C1—C2—C3—C7	−178.6 (4)	N1—C15—C16—Br2	−178.4 (4)
C2—C3—C4—C5	0.1 (8)	C15—C16—C17—C18	−1.6 (8)
C7—C3—C4—C5	176.8 (5)	Br2—C16—C17—C18	178.4 (4)
C3—C4—C5—C6	1.6 (8)	C16—C17—C18—C19	0.4 (8)
C3—C4—C5—C11	−178.0 (5)	C16—C17—C18—Br1	−178.7 (4)
C4—C5—C6—C1	−1.4 (7)	C17—C18—C19—N1	1.0 (9)
C11—C5—C6—C1	178.2 (5)	Br1—C18—C19—N1	−179.9 (4)
O1—C1—C6—C5	−178.8 (5)	C16—C15—N1—C19	−0.2 (7)
C2—C1—C6—C5	−0.3 (7)	C16—C15—N1—Co1	178.0 (4)
C4—C3—C7—C8	126.3 (5)	C18—C19—N1—C15	−1.1 (7)
C2—C3—C7—C8	−57.2 (6)	C18—C19—N1—Co1	−179.3 (4)
C4—C3—C7—C9	−113.8 (6)	C6—C1—O1—Co1	−176.9 (4)
C2—C3—C7—C9	62.7 (6)	C2—C1—O1—Co1	4.7 (5)
C4—C3—C7—C10	6.0 (7)	C3—C2—O2—Co1	174.6 (4)
C2—C3—C7—C10	−177.5 (5)	C1—C2—O2—Co1	−5.3 (5)

Symmetry code: (i) −x+2, −y+2, −z+1.

(1S_100K)

Crystal data

C38H46Br4CoN2O4	Dx = 1.537 Mg m^−3
Mr = 973.34	Ag Kα radiation, λ = 0.56085 Å
Trigonal, P3	Cell parameters from 23579 reflections
a = 20.1281 (7) Å	θ = 0.9–23.6°
c = 8.9942 (3) Å	µ = 2.27 mm^−1
V = 3155.7 (2) Å^3	T = 100 K
Z = 3	Block, blue
F(000) = 1461	0.25 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEX II CCD detector diffractometer	6428 independent reflections
Radiation source: Bruker, Kappa Apex II	3675 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.085
φ and ω scans	θmax = 23.6°, θmin = 0.9°
Absorption correction: multi-scan Bruker AXS, 2008	h = −26→28
Tmin = 0.601, Tmax = 0.713	k = −27→24
23579 measured reflections	l = −7→12

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.152	w = 1/[σ^2(Fo^2) + (0.0657P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.002
6428 reflections	Δρmax = 0.93 e Å^−3
223 parameters	Δρmin = −0.98 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.5850 (2)	0.9330 (2)	0.5125 (5)	0.0109 (8)
C2	0.5798 (2)	0.9528 (2)	0.6631 (5)	0.0125 (9)
C3	0.6136 (2)	0.9323 (2)	0.7802 (5)	0.0132 (9)
C4	0.6511 (2)	0.8928 (2)	0.7379 (5)	0.0158 (9)
H4	0.6739	0.8781	0.8140	0.019*
C5	0.6577 (2)	0.8731 (2)	0.5894 (5)	0.0147 (9)
C6	0.6232 (2)	0.8925 (2)	0.4788 (5)	0.0155 (9)
H6	0.6253	0.8784	0.3789	0.019*
C7	0.6103 (2)	0.9544 (3)	0.9412 (5)	0.0155 (9)
C8	0.6524 (3)	1.0425 (2)	0.9559 (6)	0.0198 (10)
H8A	0.6491	1.0564	1.0590	0.030*
H8B	0.6284	1.0633	0.8899	0.030*
H8C	0.7063	1.0638	0.9282	0.030*
C9	0.5265 (3)	0.9212 (3)	0.9945 (5)	0.0203 (10)
H9A	0.5262	0.9326	1.1003	0.030*
H9B	0.4984	0.8655	0.9796	0.030*
H9C	0.5018	0.9443	0.9373	0.030*
C10	0.6486 (3)	0.9238 (3)	1.0474 (6)	0.0250 (11)
H10A	0.7035	0.9485	1.0248	0.037*
H10B	0.6251	0.8682	1.0349	0.037*
H10C	0.6418	0.9353	1.1503	0.037*
C11	0.7055 (2)	0.8352 (2)	0.5586 (5)	0.0159 (9)
C12	0.6833 (4)	0.7681 (4)	0.6603 (7)	0.0470 (12)
H12A	0.7211	0.7512	0.6522	0.070*
H12B	0.6326	0.7259	0.6320	0.070*
H12C	0.6817	0.7834	0.7631	0.070*
C13	0.6972 (4)	0.8062 (4)	0.4039 (7)	0.0470 (12)
H13A	0.7193	0.8496	0.3346	0.070*
H13B	0.6427	0.7727	0.3811	0.070*
H13C	0.7241	0.7771	0.3938	0.070*
C14	0.7887 (3)	0.8933 (3)	0.5925 (10)	0.059 (2)
H14A	0.7935	0.9088	0.6970	0.088*
H14B	0.8055	0.9384	0.5288	0.088*
H14C	0.8207	0.8702	0.5735	0.088*
C15	0.6262 (2)	1.1485 (2)	0.5890 (5)	0.0160 (9)
H15	0.6093	1.1300	0.6868	0.019*
C16	0.6894 (3)	1.2212 (3)	0.5685 (5)	0.0181 (10)
C17	0.7142 (3)	1.2489 (3)	0.4270 (5)	0.0206 (10)
H17	0.7577	1.2982	0.4119	0.025*
C18	0.6744 (3)	1.2033 (3)	0.3090 (5)	0.0193 (10)
C19	0.6124 (2)	1.1304 (3)	0.3331 (5)	0.0160 (9)
H19	0.5862	1.0987	0.2504	0.019*
N1	0.5889 (2)	1.10393 (19)	0.4714 (4)	0.0133 (8)
O1	0.55234 (16)	0.95473 (16)	0.4092 (3)	0.0128 (6)
O2	0.54176 (16)	0.99113 (16)	0.6827 (3)	0.0121 (6)
Co1	0.5000	1.0000	0.5000	0.01082 (19)
Br1	0.70184 (3)	1.23597 (3)	0.11131 (6)	0.02748 (15)
Br2	0.74304 (3)	1.27900 (3)	0.73577 (6)	0.02633 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0058 (19)	0.0054 (19)	0.017 (2)	−0.0003 (16)	0.0012 (16)	0.0011 (16)
C2	0.009 (2)	0.009 (2)	0.018 (2)	0.0022 (17)	0.0018 (17)	0.0023 (17)
C3	0.010 (2)	0.012 (2)	0.014 (2)	0.0026 (17)	0.0000 (17)	−0.0007 (17)
C4	0.017 (2)	0.019 (2)	0.016 (2)	0.012 (2)	0.0019 (18)	0.0030 (18)
C5	0.016 (2)	0.010 (2)	0.022 (3)	0.0099 (18)	0.0067 (18)	0.0059 (18)
C6	0.019 (2)	0.015 (2)	0.013 (2)	0.0090 (19)	0.0044 (18)	−0.0027 (17)
C7	0.018 (2)	0.022 (2)	0.012 (2)	0.014 (2)	0.0010 (18)	0.0016 (18)
C8	0.022 (3)	0.013 (2)	0.022 (3)	0.007 (2)	−0.004 (2)	−0.0055 (19)
C9	0.023 (3)	0.018 (2)	0.017 (2)	0.008 (2)	0.002 (2)	0.0006 (19)
C10	0.035 (3)	0.034 (3)	0.017 (3)	0.026 (3)	0.000 (2)	0.001 (2)
C11	0.019 (2)	0.016 (2)	0.018 (2)	0.0120 (19)	0.0025 (19)	0.0001 (18)
C12	0.074 (3)	0.065 (3)	0.042 (3)	0.064 (3)	0.007 (2)	0.000 (2)
C13	0.074 (3)	0.065 (3)	0.042 (3)	0.064 (3)	0.007 (2)	0.000 (2)
C14	0.030 (3)	0.032 (3)	0.119 (7)	0.019 (3)	0.017 (4)	−0.009 (4)
C15	0.019 (2)	0.019 (2)	0.015 (2)	0.013 (2)	0.0001 (18)	0.0013 (18)
C16	0.018 (2)	0.016 (2)	0.020 (2)	0.008 (2)	−0.0012 (19)	−0.0043 (19)
C17	0.013 (2)	0.025 (3)	0.023 (3)	0.009 (2)	0.0020 (19)	0.003 (2)
C18	0.019 (2)	0.026 (3)	0.017 (2)	0.015 (2)	0.0038 (19)	0.007 (2)
C19	0.012 (2)	0.022 (2)	0.017 (2)	0.0108 (19)	0.0006 (18)	0.0005 (19)
N1	0.0126 (18)	0.0139 (19)	0.017 (2)	0.0092 (15)	0.0022 (15)	0.0016 (15)
O1	0.0134 (15)	0.0122 (15)	0.0133 (16)	0.0069 (13)	0.0013 (12)	0.0021 (12)
O2	0.0167 (15)	0.0100 (14)	0.0124 (16)	0.0087 (13)	0.0003 (12)	−0.0010 (12)
Co1	0.0116 (4)	0.0104 (4)	0.0113 (4)	0.0061 (3)	0.0006 (3)	0.0008 (3)
Br1	0.0262 (3)	0.0263 (3)	0.0192 (3)	0.0050 (2)	0.0062 (2)	0.0068 (2)
Br2	0.0279 (3)	0.0207 (3)	0.0207 (3)	0.0049 (2)	−0.0026 (2)	−0.0038 (2)

Geometric parameters (Å, º)

C1—O1	1.332 (5)	C12—H12A	0.9800
C1—C6	1.406 (6)	C12—H12B	0.9800
C1—C2	1.431 (6)	C12—H12C	0.9800
C2—O2	1.341 (5)	C13—H13A	0.9800
C2—C3	1.424 (6)	C13—H13B	0.9800
C3—C4	1.394 (6)	C13—H13C	0.9800
C3—C7	1.526 (6)	C14—H14A	0.9800
C4—C5	1.418 (6)	C14—H14B	0.9800
C4—H4	0.9500	C14—H14C	0.9800
C5—C6	1.376 (6)	C15—N1	1.347 (6)
C5—C11	1.524 (6)	C15—C16	1.389 (6)
C6—H6	0.9500	C15—H15	0.9500
C7—C10	1.538 (6)	C16—C17	1.379 (7)
C7—C8	1.542 (6)	C16—Br2	1.878 (5)
C7—C9	1.546 (6)	C17—C18	1.370 (7)
C8—H8A	0.9800	C17—H17	0.9500
C8—H8B	0.9800	C18—C19	1.387 (6)
C8—H8C	0.9800	C18—Br1	1.881 (5)
C9—H9A	0.9800	C19—N1	1.342 (6)
C9—H9B	0.9800	C19—H19	0.9500
C9—H9C	0.9800	N1—Co1	1.975 (3)
C10—H10A	0.9800	O1—Co1	1.889 (3)
C10—H10B	0.9800	O2—Co1	1.895 (3)
C10—H10C	0.9800	Co1—O1^i	1.889 (3)
C11—C13	1.486 (7)	Co1—O2^i	1.895 (3)
C11—C12	1.502 (7)	Co1—N1^i	1.975 (3)
C11—C14	1.519 (8)
O1—C1—C6	122.9 (4)	C11—C12—H12C	109.5
O1—C1—C2	116.8 (4)	H12A—C12—H12C	109.5
C6—C1—C2	120.2 (4)	H12B—C12—H12C	109.5
O2—C2—C3	124.3 (4)	C11—C13—H13A	109.5
O2—C2—C1	115.3 (4)	C11—C13—H13B	109.5
C3—C2—C1	120.4 (4)	H13A—C13—H13B	109.5
C4—C3—C2	115.9 (4)	C11—C13—H13C	109.5
C4—C3—C7	122.8 (4)	H13A—C13—H13C	109.5
C2—C3—C7	121.3 (4)	H13B—C13—H13C	109.5
C3—C4—C5	124.7 (4)	C11—C14—H14A	109.5
C3—C4—H4	117.6	C11—C14—H14B	109.5
C5—C4—H4	117.6	H14A—C14—H14B	109.5
C6—C5—C4	118.1 (4)	C11—C14—H14C	109.5
C6—C5—C11	123.0 (4)	H14A—C14—H14C	109.5
C4—C5—C11	118.8 (4)	H14B—C14—H14C	109.5
C5—C6—C1	120.6 (4)	N1—C15—C16	120.6 (4)
C5—C6—H6	119.7	N1—C15—H15	119.7
C1—C6—H6	119.7	C16—C15—H15	119.7
C3—C7—C10	111.6 (4)	C17—C16—C15	120.3 (4)
C3—C7—C8	109.7 (4)	C17—C16—Br2	120.6 (4)
C10—C7—C8	108.0 (4)	C15—C16—Br2	119.1 (4)
C3—C7—C9	111.5 (4)	C18—C17—C16	118.1 (4)
C10—C7—C9	106.9 (4)	C18—C17—H17	120.9
C8—C7—C9	108.9 (4)	C16—C17—H17	120.9
C7—C8—H8A	109.5	C17—C18—C19	120.2 (5)
C7—C8—H8B	109.5	C17—C18—Br1	121.8 (4)
H8A—C8—H8B	109.5	C19—C18—Br1	118.0 (4)
C7—C8—H8C	109.5	N1—C19—C18	121.1 (4)
H8A—C8—H8C	109.5	N1—C19—H19	119.4
H8B—C8—H8C	109.5	C18—C19—H19	119.4
C7—C9—H9A	109.5	C19—N1—C15	119.6 (4)
C7—C9—H9B	109.5	C19—N1—Co1	119.6 (3)
H9A—C9—H9B	109.5	C15—N1—Co1	120.7 (3)
C7—C9—H9C	109.5	C1—O1—Co1	110.1 (3)
H9A—C9—H9C	109.5	C2—O2—Co1	110.3 (3)
H9B—C9—H9C	109.5	O1^i—Co1—O1	180.0
C7—C10—H10A	109.5	O1^i—Co1—O2	92.94 (12)
C7—C10—H10B	109.5	O1—Co1—O2	87.06 (12)
H10A—C10—H10B	109.5	O1^i—Co1—O2^i	87.06 (12)
C7—C10—H10C	109.5	O1—Co1—O2^i	92.94 (12)
H10A—C10—H10C	109.5	O2—Co1—O2^i	180.00 (19)
H10B—C10—H10C	109.5	O1^i—Co1—N1^i	91.51 (13)
C13—C11—C12	107.0 (4)	O1—Co1—N1^i	88.49 (13)
C13—C11—C14	110.8 (5)	O2—Co1—N1^i	89.80 (14)
C12—C11—C14	106.8 (5)	O2^i—Co1—N1^i	90.19 (14)
C13—C11—C5	113.1 (4)	O1^i—Co1—N1	88.49 (13)
C12—C11—C5	111.2 (4)	O1—Co1—N1	91.51 (13)
C14—C11—C5	107.9 (4)	O2—Co1—N1	90.20 (14)
C11—C12—H12A	109.5	O2^i—Co1—N1	89.81 (14)
C11—C12—H12B	109.5	N1^i—Co1—N1	180.0
H12A—C12—H12B	109.5
O1—C1—C2—O2	0.3 (5)	C6—C5—C11—C14	110.3 (6)
C6—C1—C2—O2	−179.7 (4)	C4—C5—C11—C14	−66.6 (6)
O1—C1—C2—C3	−179.5 (4)	N1—C15—C16—C17	0.5 (7)
C6—C1—C2—C3	0.4 (6)	N1—C15—C16—Br2	−176.6 (3)
O2—C2—C3—C4	−179.7 (4)	C15—C16—C17—C18	0.8 (7)
C1—C2—C3—C4	0.1 (6)	Br2—C16—C17—C18	177.9 (3)
O2—C2—C3—C7	−1.2 (6)	C16—C17—C18—C19	−2.0 (7)
C1—C2—C3—C7	178.7 (4)	C16—C17—C18—Br1	178.7 (3)
C2—C3—C4—C5	0.5 (6)	C17—C18—C19—N1	1.8 (7)
C7—C3—C4—C5	−178.1 (4)	Br1—C18—C19—N1	−178.8 (3)
C3—C4—C5—C6	−1.6 (7)	C18—C19—N1—C15	−0.4 (6)
C3—C4—C5—C11	175.4 (4)	C18—C19—N1—Co1	179.7 (3)
C4—C5—C6—C1	2.1 (6)	C16—C15—N1—C19	−0.7 (6)
C11—C5—C6—C1	−174.8 (4)	C16—C15—N1—Co1	179.1 (3)
O1—C1—C6—C5	178.3 (4)	C6—C1—O1—Co1	175.2 (3)
C2—C1—C6—C5	−1.6 (6)	C2—C1—O1—Co1	−4.8 (4)
C4—C3—C7—C10	−3.2 (6)	C3—C2—O2—Co1	−175.9 (3)
C2—C3—C7—C10	178.3 (4)	C1—C2—O2—Co1	4.3 (4)
C4—C3—C7—C8	116.5 (5)	C1—O1—Co1—O2	5.7 (3)
C2—C3—C7—C8	−62.0 (5)	C1—O1—Co1—O2^i	−174.3 (3)
C4—C3—C7—C9	−122.7 (4)	C1—O1—Co1—N1^i	−84.2 (3)
C2—C3—C7—C9	58.8 (5)	C1—O1—Co1—N1	95.8 (3)
C6—C5—C11—C13	−12.5 (6)	C2—O2—Co1—O1^i	174.4 (3)
C4—C5—C11—C13	170.6 (5)	C2—O2—Co1—O1	−5.6 (3)
C6—C5—C11—C12	−133.0 (5)	C2—O2—Co1—N1^i	82.9 (3)
C4—C5—C11—C12	50.2 (6)	C2—O2—Co1—N1	−97.1 (3)

Symmetry code: (i) −x+1, −y+2, −z+1.

(1S_150K)

Crystal data

C38H46Br4CoN2O4	Dx = 1.514 Mg m^−3
Mr = 973.34	Ag Kα radiation, λ = 0.56085 Å
Trigonal, P3	Cell parameters from 13671 reflections
a = 20.255 (2) Å	θ = 0.9–20.6°
c = 9.0132 (10) Å	µ = 2.24 mm^−1
V = 3202.3 (8) Å^3	T = 150 K
Z = 3	Block, blue
F(000) = 1461	0.25 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEX II CCD detector diffractometer	4371 independent reflections
Radiation source: Bruker, Kappa Apex II	2538 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.102
φ and ω scans	θmax = 20.6°, θmin = 0.9°
Absorption correction: multi-scan Bruker AXS, 2008	h = −19→24
Tmin = 0.605, Tmax = 0.716	k = −25→24
13671 measured reflections	l = −11→9

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.070	H-atom parameters constrained
wR(F^2) = 0.187	w = 1/[σ^2(Fo^2) + (0.0787P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
4371 reflections	Δρmax = 0.81 e Å^−3
229 parameters	Δρmin = −1.21 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.3470 (4)	0.9326 (4)	0.5133 (8)	0.0186 (16)
C2	0.3717 (4)	0.9530 (4)	0.6663 (8)	0.0177 (16)
C3	0.3169 (4)	0.9327 (4)	0.7807 (8)	0.0165 (15)
C4	0.2421 (4)	0.8942 (4)	0.7382 (8)	0.0222 (17)
H4	0.2048	0.8797	0.8140	0.027*
C5	0.2158 (4)	0.8742 (4)	0.5921 (8)	0.0167 (16)
C6	0.2681 (4)	0.8926 (4)	0.4811 (8)	0.0217 (17)
H6	0.2513	0.8785	0.3817	0.026*
C7	0.3433 (4)	0.9537 (4)	0.9407 (8)	0.0220 (16)
C8	0.3888 (4)	1.0423 (4)	0.9569 (9)	0.032 (2)
H8A	0.3962	1.0559	1.0623	0.048*
H8B	0.3601	1.0639	0.9102	0.048*
H8C	0.4385	1.0627	0.9083	0.048*
C9	0.3933 (4)	0.9212 (4)	0.9962 (9)	0.0280 (18)
H9A	0.4404	0.9430	0.9378	0.042*
H9B	0.3655	0.8656	0.9852	0.042*
H9C	0.4059	0.9344	1.1010	0.042*
C10	0.2742 (5)	0.9234 (5)	1.0471 (9)	0.037 (2)
H10A	0.2922	0.9321	1.1500	0.055*
H10B	0.2405	0.8687	1.0306	0.055*
H10C	0.2461	0.9503	1.0280	0.055*
C11	0.1302 (4)	0.8357 (4)	0.5590 (9)	0.0250 (18)
C12	0.0871 (4)	0.7687 (5)	0.6621 (12)	0.048 (3)
H12A	0.1092	0.7823	0.7618	0.072*
H12B	0.0907	0.7250	0.6256	0.072*
H12C	0.0334	0.7552	0.6658	0.072*
C13	0.1094 (5)	0.8107 (7)	0.4026 (11)	0.068 (4)
H13A	0.1322	0.8553	0.3373	0.102*
H13B	0.0538	0.7839	0.3920	0.102*
H13C	0.1284	0.7763	0.3755	0.102*
C14	0.1048 (5)	0.8935 (5)	0.5921 (15)	0.068 (4)
H14A	0.1222	0.9149	0.6915	0.101*
H14B	0.0490	0.8683	0.5877	0.101*
H14C	0.1269	0.9346	0.5185	0.101*
C15	0.5231 (4)	1.1500 (4)	0.5886 (9)	0.0260 (18)
H15	0.5231	1.1324	0.6862	0.031*
C16	0.5307 (4)	1.2226 (4)	0.5651 (9)	0.0257 (18)
C17	0.5351 (4)	1.2510 (4)	0.4222 (9)	0.0291 (19)
H17	0.5409	1.3000	0.4055	0.035*
C18	0.5308 (4)	1.2052 (5)	0.3082 (9)	0.031 (2)
C19	0.5202 (4)	1.1332 (5)	0.3334 (9)	0.0274 (18)
H19	0.5157	1.1018	0.2513	0.033*
N1	0.5160 (3)	1.1068 (3)	0.4712 (7)	0.0187 (13)
O1	0.4002 (3)	0.9542 (2)	0.4095 (5)	0.0191 (11)
O2	0.4472 (3)	0.9907 (3)	0.6854 (5)	0.0183 (11)
Co1	0.5000	1.0000	0.5000	0.0150 (3)
Br1	0.53481 (6)	1.23703 (5)	0.11041 (10)	0.0464 (3)
Br2	0.53536 (5)	1.28005 (5)	0.73327 (10)	0.0407 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.021 (4)	0.014 (4)	0.021 (4)	0.009 (3)	−0.003 (3)	0.002 (3)
C2	0.019 (4)	0.009 (3)	0.021 (4)	0.004 (3)	0.001 (3)	0.002 (3)
C3	0.019 (4)	0.009 (3)	0.018 (4)	0.004 (3)	−0.001 (3)	0.000 (3)
C4	0.024 (4)	0.017 (4)	0.022 (4)	0.008 (3)	0.001 (3)	0.002 (3)
C5	0.013 (4)	0.017 (4)	0.022 (4)	0.009 (3)	0.002 (3)	0.012 (3)
C6	0.024 (4)	0.017 (4)	0.019 (4)	0.005 (3)	−0.009 (3)	−0.002 (3)
C7	0.021 (4)	0.025 (4)	0.016 (4)	0.009 (3)	0.002 (3)	−0.003 (3)
C8	0.033 (5)	0.026 (4)	0.026 (5)	0.006 (4)	0.000 (4)	−0.009 (4)
C9	0.027 (4)	0.018 (4)	0.029 (5)	0.005 (3)	0.003 (3)	0.006 (3)
C10	0.035 (5)	0.052 (6)	0.016 (5)	0.016 (4)	0.004 (4)	0.002 (4)
C11	0.019 (4)	0.025 (4)	0.025 (5)	0.007 (3)	−0.005 (3)	−0.005 (3)
C12	0.013 (4)	0.034 (5)	0.077 (8)	−0.003 (4)	−0.012 (4)	0.016 (5)
C13	0.024 (5)	0.116 (10)	0.040 (7)	0.018 (6)	−0.002 (4)	−0.018 (6)
C14	0.014 (5)	0.033 (6)	0.152 (12)	0.009 (4)	−0.017 (6)	0.003 (6)
C15	0.013 (4)	0.021 (4)	0.035 (5)	0.002 (3)	0.006 (3)	0.005 (3)
C16	0.011 (4)	0.034 (5)	0.028 (5)	0.007 (3)	0.002 (3)	−0.002 (3)
C17	0.017 (4)	0.028 (4)	0.037 (5)	0.008 (4)	−0.001 (3)	0.001 (4)
C18	0.028 (5)	0.047 (5)	0.026 (5)	0.025 (4)	0.001 (4)	0.010 (4)
C19	0.022 (4)	0.040 (5)	0.030 (5)	0.023 (4)	0.002 (3)	0.005 (4)
N1	0.011 (3)	0.025 (3)	0.017 (4)	0.007 (3)	−0.001 (2)	0.002 (3)
O1	0.023 (3)	0.014 (2)	0.014 (3)	0.005 (2)	0.000 (2)	0.004 (2)
O2	0.020 (3)	0.018 (3)	0.017 (3)	0.010 (2)	−0.004 (2)	−0.003 (2)
Co1	0.0125 (7)	0.0144 (7)	0.0161 (8)	0.0053 (6)	0.0006 (5)	0.0016 (5)
Br1	0.0686 (7)	0.0528 (6)	0.0317 (5)	0.0409 (5)	0.0027 (4)	0.0131 (4)
Br2	0.0535 (6)	0.0315 (5)	0.0348 (6)	0.0195 (4)	−0.0025 (4)	−0.0037 (4)

Geometric parameters (Å, º)

C1—O1	1.325 (8)	C12—H12A	0.9800
C1—C6	1.414 (10)	C12—H12B	0.9800
C1—C2	1.455 (10)	C12—H12C	0.9800
C2—O2	1.336 (8)	C13—H13A	0.9800
C2—C3	1.417 (10)	C13—H13B	0.9800
C3—C4	1.367 (10)	C13—H13C	0.9800
C3—C7	1.523 (10)	C14—H14A	0.9800
C4—C5	1.402 (10)	C14—H14B	0.9800
C4—H4	0.9500	C14—H14C	0.9800
C5—C6	1.366 (10)	C15—N1	1.334 (9)
C5—C11	1.534 (9)	C15—C16	1.415 (11)
C6—H6	0.9500	C15—H15	0.9500
C7—C9	1.540 (10)	C16—C17	1.395 (11)
C7—C10	1.549 (10)	C16—Br2	1.884 (8)
C7—C8	1.562 (10)	C17—C18	1.359 (11)
C8—H8A	0.9800	C17—H17	0.9500
C8—H8B	0.9800	C18—C19	1.381 (11)
C8—H8C	0.9800	C18—Br1	1.884 (8)
C9—H9A	0.9800	C19—N1	1.338 (9)
C9—H9B	0.9800	C19—H19	0.9500
C9—H9C	0.9800	N1—Co1	2.038 (6)
C10—H10A	0.9800	O1—Co1	1.933 (5)
C10—H10B	0.9800	O2—Co1	1.942 (5)
C10—H10C	0.9800	Co1—O1^i	1.933 (5)
C11—C13	1.485 (12)	Co1—O2^i	1.942 (5)
C11—C12	1.511 (11)	Co1—N1^i	2.038 (6)
C11—C14	1.527 (11)
O1—C1—C6	123.0 (7)	C11—C12—H12C	109.5
O1—C1—C2	117.9 (6)	H12A—C12—H12C	109.5
C6—C1—C2	119.1 (6)	H12B—C12—H12C	109.5
O2—C2—C3	125.3 (6)	C11—C13—H13A	109.5
O2—C2—C1	114.7 (6)	C11—C13—H13B	109.5
C3—C2—C1	120.0 (6)	H13A—C13—H13B	109.5
C4—C3—C2	116.4 (7)	C11—C13—H13C	109.5
C4—C3—C7	124.0 (6)	H13A—C13—H13C	109.5
C2—C3—C7	119.6 (6)	H13B—C13—H13C	109.5
C3—C4—C5	125.5 (7)	C11—C14—H14A	109.5
C3—C4—H4	117.3	C11—C14—H14B	109.5
C5—C4—H4	117.3	H14A—C14—H14B	109.5
C6—C5—C4	118.6 (6)	C11—C14—H14C	109.5
C6—C5—C11	121.4 (7)	H14A—C14—H14C	109.5
C4—C5—C11	119.9 (6)	H14B—C14—H14C	109.5
C5—C6—C1	120.4 (7)	N1—C15—C16	118.9 (7)
C5—C6—H6	119.8	N1—C15—H15	120.6
C1—C6—H6	119.8	C16—C15—H15	120.6
C3—C7—C9	113.8 (6)	C17—C16—C15	121.2 (7)
C3—C7—C10	110.7 (6)	C17—C16—Br2	121.0 (6)
C9—C7—C10	106.7 (6)	C15—C16—Br2	117.8 (6)
C3—C7—C8	109.4 (6)	C18—C17—C16	116.5 (7)
C9—C7—C8	109.0 (6)	C18—C17—H17	121.7
C10—C7—C8	107.0 (6)	C16—C17—H17	121.7
C7—C8—H8A	109.5	C17—C18—C19	121.3 (8)
C7—C8—H8B	109.5	C17—C18—Br1	120.3 (6)
H8A—C8—H8B	109.5	C19—C18—Br1	118.3 (6)
C7—C8—H8C	109.5	N1—C19—C18	121.3 (8)
H8A—C8—H8C	109.5	N1—C19—H19	119.3
H8B—C8—H8C	109.5	C18—C19—H19	119.3
C7—C9—H9A	109.5	C15—N1—C19	120.6 (7)
C7—C9—H9B	109.5	C15—N1—Co1	120.2 (5)
H9A—C9—H9B	109.5	C19—N1—Co1	119.2 (5)
C7—C9—H9C	109.5	C1—O1—Co1	110.1 (4)
H9A—C9—H9C	109.5	C2—O2—Co1	111.2 (4)
H9B—C9—H9C	109.5	O1—Co1—O1^i	180.0
C7—C10—H10A	109.5	O1—Co1—O2	85.60 (19)
C7—C10—H10B	109.5	O1^i—Co1—O2	94.40 (19)
H10A—C10—H10B	109.5	O1—Co1—O2^i	94.40 (19)
C7—C10—H10C	109.5	O1^i—Co1—O2^i	85.60 (19)
H10A—C10—H10C	109.5	O2—Co1—O2^i	180.0
H10B—C10—H10C	109.5	O1—Co1—N1	91.7 (2)
C13—C11—C12	109.8 (7)	O1^i—Co1—N1	88.3 (2)
C13—C11—C14	107.5 (8)	O2—Co1—N1	90.0 (2)
C12—C11—C14	107.7 (8)	O2^i—Co1—N1	90.0 (2)
C13—C11—C5	114.5 (7)	O1—Co1—N1^i	88.3 (2)
C12—C11—C5	109.6 (6)	O1^i—Co1—N1^i	91.7 (2)
C14—C11—C5	107.5 (6)	O2—Co1—N1^i	90.0 (2)
C11—C12—H12A	109.5	O2^i—Co1—N1^i	90.0 (2)
C11—C12—H12B	109.5	N1—Co1—N1^i	180.0
H12A—C12—H12B	109.5
O1—C1—C2—O2	−1.4 (9)	C6—C5—C11—C13	8.5 (11)
C6—C1—C2—O2	−180.0 (6)	C4—C5—C11—C13	−174.3 (8)
O1—C1—C2—C3	178.7 (6)	C6—C5—C11—C12	132.4 (8)
C6—C1—C2—C3	0.1 (9)	C4—C5—C11—C12	−50.4 (9)
O2—C2—C3—C4	179.9 (6)	C6—C5—C11—C14	−110.8 (9)
C1—C2—C3—C4	−0.2 (9)	C4—C5—C11—C14	66.4 (9)
O2—C2—C3—C7	−0.5 (10)	N1—C15—C16—C17	−3.7 (10)
C1—C2—C3—C7	179.4 (6)	N1—C15—C16—Br2	176.8 (5)
C2—C3—C4—C5	−0.7 (10)	C15—C16—C17—C18	0.8 (10)
C7—C3—C4—C5	179.8 (6)	Br2—C16—C17—C18	−179.7 (5)
C3—C4—C5—C6	1.5 (11)	C16—C17—C18—C19	2.0 (11)
C3—C4—C5—C11	−175.8 (6)	C16—C17—C18—Br1	179.2 (5)
C4—C5—C6—C1	−1.5 (10)	C17—C18—C19—N1	−2.0 (11)
C11—C5—C6—C1	175.8 (6)	Br1—C18—C19—N1	−179.2 (5)
O1—C1—C6—C5	−177.7 (6)	C16—C15—N1—C19	3.7 (10)
C2—C1—C6—C5	0.7 (10)	C16—C15—N1—Co1	−177.2 (5)
C4—C3—C7—C9	121.7 (7)	C18—C19—N1—C15	−1.0 (10)
C2—C3—C7—C9	−57.8 (8)	C18—C19—N1—Co1	179.9 (5)
C4—C3—C7—C10	1.6 (10)	C6—C1—O1—Co1	−175.6 (5)
C2—C3—C7—C10	−177.9 (6)	C2—C1—O1—Co1	5.9 (7)
C4—C3—C7—C8	−116.1 (7)	C3—C2—O2—Co1	176.0 (5)
C2—C3—C7—C8	64.4 (8)	C1—C2—O2—Co1	−3.9 (7)

Symmetry code: (i) −x+1, −y+2, −z+1.

(1S_175K)

Crystal data

C38H46Br4CoN2O4	Dx = 1.500 Mg m^−3
Mr = 973.34	Ag Kα radiation, λ = 0.56085 Å
Trigonal, P3	Cell parameters from 33637 reflections
a = 20.3624 (10) Å	θ = 0.9–23.7°
c = 9.0045 (5) Å	µ = 2.22 mm^−1
V = 3233.3 (4) Å^3	T = 175 K
Z = 3	Block, blue
F(000) = 1461	0.25 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEX II CCD detector diffractometer	6344 independent reflections
Radiation source: Bruker, Kappa Apex II	3377 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.092
φ and ω scans	θmax = 23.7°, θmin = 0.9°
Absorption correction: multi-scan Bruker AXS, 2008	h = −29→27
Tmin = 0.607, Tmax = 0.718	k = −29→24
33637 measured reflections	l = −11→12

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.073	H-atom parameters constrained
wR(F^2) = 0.204	w = 1/[σ^2(Fo^2) + (0.0893P)^2 + 4.9086P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
6344 reflections	Δρmax = 0.72 e Å^−3
229 parameters	Δρmin = −1.22 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.4121 (3)	0.0665 (3)	0.9844 (6)	0.0202 (10)
C2	0.4174 (3)	0.0466 (3)	0.8331 (6)	0.0201 (11)
C3	0.3833 (3)	0.0671 (3)	0.7169 (6)	0.0243 (11)
C4	0.3456 (3)	0.1045 (3)	0.7573 (7)	0.0271 (12)
H4	0.3222	0.1177	0.6809	0.033*
C5	0.3393 (3)	0.1247 (3)	0.9058 (6)	0.0256 (12)
C6	0.3726 (3)	0.1061 (3)	1.0183 (6)	0.0239 (11)
H6	0.3693	0.1195	1.1180	0.029*
C7	0.3874 (3)	0.0449 (3)	0.5552 (6)	0.0287 (12)
C8	0.4709 (3)	0.0786 (4)	0.5044 (7)	0.0365 (14)
H8A	0.4977	0.1338	0.5166	0.055*
H8B	0.4721	0.0662	0.3996	0.055*
H8C	0.4956	0.0572	0.5647	0.055*
C9	0.3460 (4)	−0.0423 (3)	0.5409 (7)	0.0379 (15)
H9A	0.3699	−0.0626	0.6069	0.057*
H9B	0.3492	−0.0561	0.4380	0.057*
H9C	0.2926	−0.0636	0.5687	0.057*
C10	0.3492 (4)	0.0749 (4)	0.4492 (7)	0.0448 (17)
H10A	0.2968	0.0564	0.4812	0.067*
H10B	0.3493	0.0570	0.3482	0.067*
H10C	0.3772	0.1305	0.4506	0.067*
C11	0.2939 (3)	0.1642 (3)	0.9381 (7)	0.0294 (13)
C12	0.3205 (4)	0.2327 (4)	0.8379 (9)	0.052 (2)
H12A	0.2904	0.2572	0.8577	0.079*
H12B	0.3140	0.2165	0.7338	0.079*
H12C	0.3741	0.2687	0.8572	0.079*
C13	0.2972 (6)	0.1873 (6)	1.0954 (9)	0.071 (3)
H13A	0.3503	0.2196	1.1251	0.106*
H13B	0.2734	0.1421	1.1586	0.106*
H13C	0.2702	0.2156	1.1065	0.106*
C14	0.2102 (4)	0.1084 (4)	0.8959 (12)	0.068 (3)
H14A	0.1901	0.0635	0.9601	0.103*
H14B	0.2076	0.0929	0.7920	0.103*
H14C	0.1801	0.1333	0.9089	0.103*
C15	0.3684 (3)	−0.1538 (3)	0.9163 (7)	0.0326 (13)
H15	0.3839	−0.1359	0.8179	0.039*
C16	0.3054 (3)	−0.2257 (3)	0.9381 (7)	0.0317 (13)
C17	0.2819 (4)	−0.2536 (4)	1.0797 (7)	0.0365 (14)
H17	0.2384	−0.3020	1.0959	0.044*
C18	0.3235 (3)	−0.2089 (4)	1.1953 (7)	0.0359 (14)
C19	0.3846 (3)	−0.1379 (4)	1.1696 (7)	0.0352 (14)
H19	0.4119	−0.1072	1.2520	0.042*
N1	0.4071 (3)	−0.1101 (3)	1.0298 (5)	0.0274 (10)
O1	0.4436 (2)	0.0466 (2)	1.0880 (4)	0.0250 (8)
O2	0.4541 (2)	0.01003 (19)	0.8117 (4)	0.0237 (8)
Co1	0.5000	0.0000	1.0000	0.0185 (2)
Br1	0.29720 (4)	−0.23959 (4)	1.39293 (8)	0.0550 (3)
Br2	0.25137 (4)	−0.28270 (4)	0.77087 (8)	0.0496 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.022 (2)	0.017 (2)	0.018 (3)	0.008 (2)	0.004 (2)	0.003 (2)
C2	0.020 (2)	0.013 (2)	0.026 (3)	0.0076 (19)	0.003 (2)	0.004 (2)
C3	0.031 (3)	0.021 (2)	0.022 (3)	0.013 (2)	0.002 (2)	−0.002 (2)
C4	0.031 (3)	0.023 (3)	0.028 (3)	0.014 (2)	−0.002 (2)	0.006 (2)
C5	0.032 (3)	0.026 (3)	0.026 (3)	0.019 (2)	0.006 (2)	0.000 (2)
C6	0.035 (3)	0.022 (2)	0.019 (3)	0.017 (2)	0.008 (2)	0.002 (2)
C7	0.037 (3)	0.032 (3)	0.021 (3)	0.020 (2)	−0.003 (2)	0.000 (2)
C8	0.040 (3)	0.045 (4)	0.023 (3)	0.020 (3)	0.002 (3)	−0.003 (3)
C9	0.050 (4)	0.035 (3)	0.031 (4)	0.022 (3)	−0.006 (3)	−0.008 (3)
C10	0.073 (5)	0.062 (4)	0.019 (3)	0.049 (4)	0.003 (3)	0.002 (3)
C11	0.037 (3)	0.024 (3)	0.035 (3)	0.021 (2)	0.005 (3)	−0.001 (2)
C12	0.068 (5)	0.041 (4)	0.069 (6)	0.042 (4)	0.023 (4)	0.013 (4)
C13	0.103 (7)	0.105 (7)	0.054 (5)	0.089 (6)	0.006 (5)	−0.011 (5)
C14	0.040 (4)	0.045 (4)	0.123 (9)	0.024 (4)	0.015 (5)	−0.007 (5)
C15	0.037 (3)	0.038 (3)	0.031 (3)	0.025 (3)	−0.002 (3)	−0.002 (3)
C16	0.033 (3)	0.025 (3)	0.038 (4)	0.015 (2)	0.002 (3)	−0.002 (3)
C17	0.040 (3)	0.038 (3)	0.037 (4)	0.023 (3)	0.004 (3)	0.005 (3)
C18	0.029 (3)	0.047 (4)	0.035 (4)	0.021 (3)	0.010 (3)	0.012 (3)
C19	0.031 (3)	0.052 (4)	0.030 (3)	0.025 (3)	0.004 (3)	0.006 (3)
N1	0.029 (2)	0.034 (2)	0.027 (3)	0.021 (2)	0.001 (2)	0.000 (2)
O1	0.038 (2)	0.0234 (18)	0.018 (2)	0.0186 (17)	0.0018 (16)	0.0021 (15)
O2	0.0264 (18)	0.0231 (18)	0.024 (2)	0.0140 (15)	0.0051 (16)	0.0005 (15)
Co1	0.0205 (5)	0.0174 (5)	0.0195 (5)	0.0108 (4)	0.0012 (4)	0.0028 (4)
Br1	0.0499 (4)	0.0642 (5)	0.0364 (4)	0.0176 (4)	0.0133 (3)	0.0177 (3)
Br2	0.0551 (4)	0.0402 (4)	0.0403 (4)	0.0139 (3)	−0.0011 (3)	−0.0046 (3)

Geometric parameters (Å, º)

C1—O1	1.305 (6)	C12—H12A	0.9800
C1—C6	1.430 (7)	C12—H12B	0.9800
C1—C2	1.440 (7)	C12—H12C	0.9800
C2—O2	1.305 (6)	C13—H13A	0.9800
C2—C3	1.429 (7)	C13—H13B	0.9800
C3—C4	1.372 (7)	C13—H13C	0.9800
C3—C7	1.538 (8)	C14—H14A	0.9800
C4—C5	1.424 (8)	C14—H14B	0.9800
C4—H4	0.9500	C14—H14C	0.9800
C5—C6	1.373 (8)	C15—N1	1.326 (8)
C5—C11	1.527 (7)	C15—C16	1.397 (8)
C6—H6	0.9500	C15—H15	0.9500
C7—C10	1.537 (8)	C16—C17	1.380 (9)
C7—C9	1.544 (8)	C16—Br2	1.883 (6)
C7—C8	1.551 (8)	C17—C18	1.363 (9)
C8—H8A	0.9800	C17—H17	0.9500
C8—H8B	0.9800	C18—C19	1.376 (9)
C8—H8C	0.9800	C18—Br1	1.873 (6)
C9—H9A	0.9800	C19—N1	1.363 (8)
C9—H9B	0.9800	C19—H19	0.9500
C9—H9C	0.9800	N1—Co1	2.106 (5)
C10—H10A	0.9800	O1—Co1	1.985 (4)
C10—H10B	0.9800	O2—Co1	1.995 (4)
C10—H10C	0.9800	Co1—O1^i	1.985 (4)
C11—C13	1.483 (10)	Co1—O2^i	1.995 (4)
C11—C12	1.516 (9)	Co1—N1^i	2.106 (5)
C11—C14	1.550 (10)
O1—C1—C6	121.6 (5)	C11—C12—H12C	109.5
O1—C1—C2	118.1 (4)	H12A—C12—H12C	109.5
C6—C1—C2	120.2 (5)	H12B—C12—H12C	109.5
O2—C2—C3	124.0 (5)	C11—C13—H13A	109.5
O2—C2—C1	116.4 (5)	C11—C13—H13B	109.5
C3—C2—C1	119.6 (4)	H13A—C13—H13B	109.5
C4—C3—C2	117.2 (5)	C11—C13—H13C	109.5
C4—C3—C7	122.7 (5)	H13A—C13—H13C	109.5
C2—C3—C7	120.1 (5)	H13B—C13—H13C	109.5
C3—C4—C5	124.5 (5)	C11—C14—H14A	109.5
C3—C4—H4	117.8	C11—C14—H14B	109.5
C5—C4—H4	117.8	H14A—C14—H14B	109.5
C6—C5—C4	119.0 (5)	C11—C14—H14C	109.5
C6—C5—C11	121.1 (5)	H14A—C14—H14C	109.5
C4—C5—C11	119.9 (5)	H14B—C14—H14C	109.5
C5—C6—C1	119.5 (5)	N1—C15—C16	121.4 (6)
C5—C6—H6	120.2	N1—C15—H15	119.3
C1—C6—H6	120.2	C16—C15—H15	119.3
C10—C7—C3	111.1 (5)	C17—C16—C15	120.6 (6)
C10—C7—C9	108.2 (5)	C17—C16—Br2	120.6 (5)
C3—C7—C9	109.8 (5)	C15—C16—Br2	118.7 (5)
C10—C7—C8	107.5 (5)	C18—C17—C16	117.3 (6)
C3—C7—C8	110.9 (5)	C18—C17—H17	121.3
C9—C7—C8	109.3 (5)	C16—C17—H17	121.3
C7—C8—H8A	109.5	C17—C18—C19	120.4 (6)
C7—C8—H8B	109.5	C17—C18—Br1	121.6 (5)
H8A—C8—H8B	109.5	C19—C18—Br1	117.9 (5)
C7—C8—H8C	109.5	N1—C19—C18	122.1 (6)
H8A—C8—H8C	109.5	N1—C19—H19	118.9
H8B—C8—H8C	109.5	C18—C19—H19	118.9
C7—C9—H9A	109.5	C15—N1—C19	118.0 (5)
C7—C9—H9B	109.5	C15—N1—Co1	122.2 (4)
H9A—C9—H9B	109.5	C19—N1—Co1	119.8 (4)
C7—C9—H9C	109.5	C1—O1—Co1	110.7 (3)
H9A—C9—H9C	109.5	C2—O2—Co1	111.4 (3)
H9B—C9—H9C	109.5	O1^i—Co1—O1	180.0
C7—C10—H10A	109.5	O1^i—Co1—O2	97.05 (14)
C7—C10—H10B	109.5	O1—Co1—O2	82.95 (14)
H10A—C10—H10B	109.5	O1^i—Co1—O2^i	82.95 (14)
C7—C10—H10C	109.5	O1—Co1—O2^i	97.05 (14)
H10A—C10—H10C	109.5	O2—Co1—O2^i	180.0
H10B—C10—H10C	109.5	O1^i—Co1—N1	88.20 (16)
C13—C11—C12	109.8 (6)	O1—Co1—N1	91.80 (16)
C13—C11—C5	113.9 (5)	O2—Co1—N1	89.98 (16)
C12—C11—C5	109.8 (5)	O2^i—Co1—N1	90.02 (16)
C13—C11—C14	109.1 (6)	O1^i—Co1—N1^i	91.80 (16)
C12—C11—C14	106.6 (6)	O1—Co1—N1^i	88.20 (16)
C5—C11—C14	107.4 (5)	O2—Co1—N1^i	90.02 (16)
C11—C12—H12A	109.5	O2^i—Co1—N1^i	89.98 (16)
C11—C12—H12B	109.5	N1—Co1—N1^i	180.0
H12A—C12—H12B	109.5
O1—C1—C2—O2	−0.4 (6)	C6—C5—C11—C13	6.6 (9)
C6—C1—C2—O2	−179.6 (4)	C4—C5—C11—C13	−175.4 (6)
O1—C1—C2—C3	179.7 (4)	C6—C5—C11—C12	130.2 (6)
C6—C1—C2—C3	0.5 (7)	C4—C5—C11—C12	−51.8 (7)
O2—C2—C3—C4	179.0 (5)	C6—C5—C11—C14	−114.3 (7)
C1—C2—C3—C4	−1.1 (7)	C4—C5—C11—C14	63.7 (7)
O2—C2—C3—C7	1.1 (8)	N1—C15—C16—C17	−0.5 (8)
C1—C2—C3—C7	−178.9 (4)	N1—C15—C16—Br2	177.7 (4)
C2—C3—C4—C5	0.9 (8)	C15—C16—C17—C18	−1.4 (8)
C7—C3—C4—C5	178.7 (5)	Br2—C16—C17—C18	−179.5 (4)
C3—C4—C5—C6	−0.1 (8)	C16—C17—C18—C19	2.4 (9)
C3—C4—C5—C11	−178.2 (5)	C16—C17—C18—Br1	179.4 (4)
C4—C5—C6—C1	−0.5 (8)	C17—C18—C19—N1	−1.7 (9)
C11—C5—C6—C1	177.5 (5)	Br1—C18—C19—N1	−178.8 (4)
O1—C1—C6—C5	−178.9 (5)	C16—C15—N1—C19	1.3 (8)
C2—C1—C6—C5	0.3 (7)	C16—C15—N1—Co1	−177.8 (4)
C4—C3—C7—C10	4.0 (8)	C18—C19—N1—C15	−0.3 (8)
C2—C3—C7—C10	−178.3 (5)	C18—C19—N1—Co1	178.9 (4)
C4—C3—C7—C9	−115.6 (6)	C6—C1—O1—Co1	−175.6 (4)
C2—C3—C7—C9	62.1 (7)	C2—C1—O1—Co1	5.1 (5)
C4—C3—C7—C8	123.5 (6)	C3—C2—O2—Co1	175.3 (4)
C2—C3—C7—C8	−58.8 (6)	C1—C2—O2—Co1	−4.6 (5)

Symmetry code: (i) −x+1, −y, −z+2.

(1S_200K)

Crystal data

C38H46Br4CoN2O4	Dx = 1.482 Mg m^−3
Mr = 973.34	Ag Kα radiation, λ = 0.56085 Å
Trigonal, P3	Cell parameters from 11725 reflections
a = 20.4697 (14) Å	θ = 0.9–20.6°
c = 9.0166 (6) Å	µ = 2.19 mm^−1
V = 3271.9 (5) Å^3	T = 200 K
Z = 3	Block, blue
F(000) = 1461	0.25 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEX II CCD detector diffractometer	4475 independent reflections
Radiation source: Bruker, Kappa Apex II	2029 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.110
φ and ω scans	θmax = 20.6°, θmin = 0.9°
Absorption correction: multi-scan Bruker AXS, 2008	h = −7→25
Tmin = 0.611, Tmax = 0.721	k = −24→25
11725 measured reflections	l = −10→11

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.071	H-atom parameters constrained
wR(F^2) = 0.199	w = 1/[σ^2(Fo^2) + (0.0782P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.89	(Δ/σ)max < 0.001
4475 reflections	Δρmax = 0.67 e Å^−3
229 parameters	Δρmin = −0.81 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.3444 (4)	0.9333 (4)	0.9869 (7)	0.0242 (17)
C2	0.3707 (4)	0.9543 (4)	0.8323 (8)	0.0277 (17)
C3	0.3157 (5)	0.9333 (4)	0.7152 (7)	0.0321 (19)
C4	0.2416 (4)	0.8962 (4)	0.7554 (8)	0.0308 (18)
H4	0.2049	0.8831	0.6794	0.037*
C5	0.2148 (4)	0.8752 (5)	0.9079 (8)	0.0335 (19)
C6	0.2675 (4)	0.8953 (5)	1.0165 (8)	0.0341 (19)
H6	0.2512	0.8830	1.1164	0.041*
C7	0.3421 (5)	0.9558 (5)	0.5543 (7)	0.038 (2)
C8	0.3905 (5)	0.9218 (5)	0.5028 (8)	0.047 (2)
H8A	0.4383	0.9456	0.5573	0.071*
H8B	0.4006	0.9308	0.3963	0.071*
H8C	0.3634	0.8674	0.5221	0.071*
C9	0.3865 (6)	1.0418 (5)	0.5411 (8)	0.048 (2)
H9A	0.3558	1.0627	0.5782	0.072*
H9B	0.3994	1.0561	0.4369	0.072*
H9C	0.4329	1.0618	0.5997	0.072*
C10	0.2744 (5)	0.9267 (5)	0.4490 (8)	0.050 (3)
H10A	0.2420	0.9469	0.4795	0.075*
H10B	0.2455	0.8715	0.4525	0.075*
H10C	0.2923	0.9432	0.3476	0.075*
C11	0.1300 (5)	0.8366 (5)	0.9362 (8)	0.037 (2)
C12	0.0879 (6)	0.7686 (6)	0.8370 (11)	0.070 (3)
H12A	0.1087	0.7350	0.8491	0.105*
H12B	0.0932	0.7850	0.7334	0.105*
H12C	0.0343	0.7416	0.8642	0.105*
C13	0.1104 (6)	0.8124 (7)	1.0953 (10)	0.076 (4)
H13A	0.1307	0.8571	1.1591	0.114*
H13B	0.1323	0.7813	1.1241	0.114*
H13C	0.0555	0.7831	1.1064	0.114*
C14	0.1021 (6)	0.8922 (6)	0.8979 (14)	0.082 (4)
H14A	0.0490	0.8700	0.9262	0.122*
H14B	0.1074	0.9023	0.7911	0.122*
H14C	0.1323	0.9395	0.9523	0.122*
C15	0.4771 (5)	0.8615 (5)	0.8309 (9)	0.038 (2)
H15	0.4804	0.8923	0.7493	0.046*
C16	0.4674 (5)	0.7907 (5)	0.8041 (9)	0.042 (2)
C17	0.4630 (5)	0.7445 (5)	0.9192 (8)	0.041 (2)
H17	0.4561	0.6956	0.9027	0.049*
C18	0.4692 (5)	0.7733 (5)	1.0588 (9)	0.040 (2)
C19	0.4782 (4)	0.8445 (5)	1.0825 (9)	0.040 (2)
H19	0.4816	0.8626	1.1808	0.048*
N1	0.4820 (4)	0.8877 (4)	0.9675 (7)	0.0357 (17)
O1	0.3959 (3)	0.9537 (3)	1.0869 (5)	0.0323 (13)
O2	0.4425 (3)	0.9901 (3)	0.8111 (5)	0.0302 (12)
Co1	0.5000	1.0000	1.0000	0.0272 (4)
Br1	0.46602 (7)	0.71661 (6)	1.22765 (10)	0.0615 (4)
Br2	0.46246 (7)	0.75935 (6)	0.60651 (10)	0.0663 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.022 (4)	0.012 (4)	0.029 (3)	0.002 (3)	−0.009 (3)	−0.007 (3)
C2	0.023 (4)	0.029 (4)	0.034 (4)	0.015 (4)	−0.002 (3)	−0.005 (3)
C3	0.037 (5)	0.027 (5)	0.025 (4)	0.011 (4)	0.000 (3)	0.003 (3)
C4	0.031 (5)	0.029 (5)	0.028 (4)	0.011 (4)	−0.005 (3)	0.002 (3)
C5	0.022 (4)	0.032 (5)	0.041 (4)	0.010 (4)	0.001 (4)	−0.002 (4)
C6	0.025 (5)	0.037 (5)	0.037 (4)	0.012 (4)	0.006 (4)	−0.002 (4)
C7	0.040 (5)	0.054 (6)	0.020 (3)	0.025 (5)	0.007 (4)	0.006 (4)
C8	0.054 (6)	0.056 (6)	0.029 (4)	0.025 (5)	0.004 (4)	0.000 (4)
C9	0.066 (7)	0.045 (6)	0.030 (4)	0.026 (5)	−0.001 (4)	0.014 (4)
C10	0.044 (6)	0.058 (7)	0.028 (4)	0.010 (5)	−0.010 (4)	−0.006 (4)
C11	0.029 (5)	0.038 (5)	0.041 (4)	0.015 (4)	0.000 (4)	−0.003 (4)
C12	0.033 (6)	0.060 (7)	0.095 (8)	0.007 (5)	0.008 (5)	−0.020 (6)
C13	0.033 (6)	0.119 (10)	0.054 (6)	0.020 (7)	0.001 (5)	0.014 (6)
C14	0.040 (7)	0.069 (8)	0.147 (11)	0.036 (6)	0.018 (7)	0.022 (8)
C15	0.033 (5)	0.046 (6)	0.043 (5)	0.025 (5)	−0.004 (4)	0.000 (4)
C16	0.043 (6)	0.050 (6)	0.038 (4)	0.027 (5)	0.003 (4)	−0.012 (4)
C17	0.039 (5)	0.037 (5)	0.043 (4)	0.016 (4)	−0.004 (4)	−0.008 (4)
C18	0.037 (5)	0.029 (5)	0.052 (5)	0.016 (4)	0.000 (4)	0.010 (4)
C19	0.024 (5)	0.037 (5)	0.047 (5)	0.006 (4)	−0.005 (4)	−0.002 (4)
N1	0.035 (4)	0.040 (4)	0.034 (3)	0.019 (4)	0.002 (3)	−0.006 (3)
O1	0.022 (3)	0.038 (3)	0.028 (2)	0.007 (3)	−0.007 (2)	−0.006 (2)
O2	0.030 (3)	0.034 (3)	0.025 (2)	0.015 (3)	0.005 (2)	0.001 (2)
Co1	0.0245 (8)	0.0261 (8)	0.0287 (7)	0.0108 (7)	−0.0025 (6)	−0.0034 (6)
Br1	0.0833 (8)	0.0498 (7)	0.0552 (6)	0.0361 (6)	0.0052 (5)	0.0077 (5)
Br2	0.0914 (9)	0.0730 (8)	0.0492 (5)	0.0522 (7)	−0.0048 (5)	−0.0214 (5)

Geometric parameters (Å, º)

C1—O1	1.289 (8)	C12—H12A	0.9800
C1—C6	1.388 (10)	C12—H12B	0.9800
C1—C2	1.478 (9)	C12—H12C	0.9800
C2—O2	1.286 (9)	C13—H13A	0.9800
C2—C3	1.443 (10)	C13—H13B	0.9800
C3—C4	1.364 (11)	C13—H13C	0.9800
C3—C7	1.536 (9)	C14—H14A	0.9800
C4—C5	1.464 (10)	C14—H14B	0.9800
C4—H4	0.9500	C14—H14C	0.9800
C5—C6	1.360 (10)	C15—N1	1.326 (9)
C5—C11	1.527 (11)	C15—C16	1.382 (12)
C6—H6	0.9500	C15—H15	0.9500
C7—C9	1.530 (12)	C16—C17	1.376 (11)
C7—C10	1.534 (11)	C16—Br2	1.880 (8)
C7—C8	1.540 (12)	C17—C18	1.369 (11)
C8—H8A	0.9800	C17—H17	0.9500
C8—H8B	0.9800	C18—C19	1.391 (12)
C8—H8C	0.9800	C18—Br1	1.896 (8)
C9—H9A	0.9800	C19—N1	1.338 (10)
C9—H9B	0.9800	C19—H19	0.9500
C9—H9C	0.9800	N1—Co1	2.159 (7)
C10—H10A	0.9800	O1—Co1	2.009 (5)
C10—H10B	0.9800	O2—Co1	2.023 (5)
C10—H10C	0.9800	Co1—O1^i	2.009 (5)
C11—C13	1.505 (11)	Co1—O2^i	2.023 (5)
C11—C12	1.512 (12)	Co1—N1^i	2.159 (7)
C11—C14	1.544 (13)
O1—C1—C6	124.2 (6)	C11—C12—H12C	109.5
O1—C1—C2	116.4 (6)	H12A—C12—H12C	109.5
C6—C1—C2	119.4 (6)	H12B—C12—H12C	109.5
O2—C2—C3	124.0 (6)	C11—C13—H13A	109.5
O2—C2—C1	116.9 (6)	C11—C13—H13B	109.5
C3—C2—C1	119.1 (7)	H13A—C13—H13B	109.5
C4—C3—C2	117.2 (6)	C11—C13—H13C	109.5
C4—C3—C7	123.0 (7)	H13A—C13—H13C	109.5
C2—C3—C7	119.8 (7)	H13B—C13—H13C	109.5
C3—C4—C5	124.2 (7)	C11—C14—H14A	109.5
C3—C4—H4	117.9	C11—C14—H14B	109.5
C5—C4—H4	117.9	H14A—C14—H14B	109.5
C6—C5—C4	117.6 (7)	C11—C14—H14C	109.5
C6—C5—C11	124.2 (7)	H14A—C14—H14C	109.5
C4—C5—C11	118.1 (7)	H14B—C14—H14C	109.5
C5—C6—C1	122.5 (7)	N1—C15—C16	121.9 (8)
C5—C6—H6	118.8	N1—C15—H15	119.1
C1—C6—H6	118.8	C16—C15—H15	119.1
C9—C7—C10	107.5 (7)	C17—C16—C15	120.9 (7)
C9—C7—C3	109.7 (6)	C17—C16—Br2	120.4 (7)
C10—C7—C3	110.8 (7)	C15—C16—Br2	118.6 (7)
C9—C7—C8	110.5 (7)	C18—C17—C16	115.9 (8)
C10—C7—C8	107.4 (7)	C18—C17—H17	122.0
C3—C7—C8	111.0 (7)	C16—C17—H17	122.0
C7—C8—H8A	109.5	C17—C18—C19	121.8 (8)
C7—C8—H8B	109.5	C17—C18—Br1	120.5 (7)
H8A—C8—H8B	109.5	C19—C18—Br1	117.7 (6)
C7—C8—H8C	109.5	N1—C19—C18	120.4 (8)
H8A—C8—H8C	109.5	N1—C19—H19	119.8
H8B—C8—H8C	109.5	C18—C19—H19	119.8
C7—C9—H9A	109.5	C15—N1—C19	119.0 (7)
C7—C9—H9B	109.5	C15—N1—Co1	119.6 (6)
H9A—C9—H9B	109.5	C19—N1—Co1	121.3 (5)
C7—C9—H9C	109.5	C1—O1—Co1	112.5 (4)
H9A—C9—H9C	109.5	C2—O2—Co1	111.9 (4)
H9B—C9—H9C	109.5	O1—Co1—O1^i	180.0
C7—C10—H10A	109.5	O1—Co1—O2^i	98.39 (19)
C7—C10—H10B	109.5	O1^i—Co1—O2^i	81.61 (19)
H10A—C10—H10B	109.5	O1—Co1—O2	81.61 (19)
C7—C10—H10C	109.5	O1^i—Co1—O2	98.39 (19)
H10A—C10—H10C	109.5	O2^i—Co1—O2	180.00 (12)
H10B—C10—H10C	109.5	O1—Co1—N1^i	91.4 (2)
C13—C11—C12	109.0 (8)	O1^i—Co1—N1^i	88.6 (2)
C13—C11—C5	112.1 (7)	O2^i—Co1—N1^i	89.9 (2)
C12—C11—C5	110.8 (7)	O2—Co1—N1^i	90.1 (2)
C13—C11—C14	108.7 (9)	O1—Co1—N1	88.6 (2)
C12—C11—C14	107.2 (8)	O1^i—Co1—N1	91.4 (2)
C5—C11—C14	109.0 (7)	O2^i—Co1—N1	90.1 (2)
C11—C12—H12A	109.5	O2—Co1—N1	89.9 (2)
C11—C12—H12B	109.5	N1^i—Co1—N1	180.0
H12A—C12—H12B	109.5
O1—C1—C2—O2	0.9 (10)	C6—C5—C11—C13	−9.0 (13)
C6—C1—C2—O2	179.3 (7)	C4—C5—C11—C13	175.0 (8)
O1—C1—C2—C3	−179.8 (7)	C6—C5—C11—C12	−130.9 (9)
C6—C1—C2—C3	−1.5 (11)	C4—C5—C11—C12	53.1 (10)
O2—C2—C3—C4	−179.3 (7)	C6—C5—C11—C14	111.3 (10)
C1—C2—C3—C4	1.5 (11)	C4—C5—C11—C14	−64.7 (10)
O2—C2—C3—C7	−1.8 (12)	N1—C15—C16—C17	−0.5 (13)
C1—C2—C3—C7	179.0 (7)	N1—C15—C16—Br2	−179.1 (6)
C2—C3—C4—C5	−1.4 (12)	C15—C16—C17—C18	−0.3 (13)
C7—C3—C4—C5	−178.8 (8)	Br2—C16—C17—C18	178.3 (7)
C3—C4—C5—C6	1.2 (13)	C16—C17—C18—C19	1.0 (13)
C3—C4—C5—C11	177.5 (8)	C16—C17—C18—Br1	−178.8 (6)
C4—C5—C6—C1	−1.1 (12)	C17—C18—C19—N1	−0.9 (13)
C11—C5—C6—C1	−177.1 (8)	Br1—C18—C19—N1	178.9 (6)
O1—C1—C6—C5	179.5 (8)	C16—C15—N1—C19	0.7 (12)
C2—C1—C6—C5	1.3 (12)	C16—C15—N1—Co1	178.5 (6)
C4—C3—C7—C9	115.1 (9)	C18—C19—N1—C15	0.0 (12)
C2—C3—C7—C9	−62.2 (10)	C18—C19—N1—Co1	−177.7 (6)
C4—C3—C7—C10	−3.4 (11)	C6—C1—O1—Co1	175.5 (6)
C2—C3—C7—C10	179.3 (7)	C2—C1—O1—Co1	−6.2 (8)
C4—C3—C7—C8	−122.6 (9)	C3—C2—O2—Co1	−174.4 (6)
C2—C3—C7—C8	60.1 (10)	C1—C2—O2—Co1	4.8 (8)

Symmetry code: (i) −x+1, −y+2, −z+2.

(1S_296K)

Crystal data

C38H46Br4CoN2O4	Dx = 1.445 Mg m^−3
Mr = 973.34	Ag Kα radiation, λ = 0.56085 Å
Trigonal, P3	Cell parameters from 28207 reflections
a = 20.688 (3) Å	θ = 0.9–20.6°
c = 9.0563 (15) Å	µ = 2.13 mm^−1
V = 3356.6 (12) Å^3	T = 296 K
Z = 3	Block, blue
F(000) = 1461	0.25 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEX II CCD detector diffractometer	4605 independent reflections
Radiation source: Bruker, Kappa Apex II	2101 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.135
φ and ω scans	θmax = 20.6°, θmin = 0.9°
Absorption correction: multi-scan Bruker AXS, 2008	h = −25→25
Tmin = 0.618, Tmax = 0.726	k = −25→25
28207 measured reflections	l = −10→11

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.075	H-atom parameters constrained
wR(F^2) = 0.227	w = 1/[σ^2(Fo^2) + (0.0998P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
4605 reflections	Δρmax = 0.70 e Å^−3
229 parameters	Δρmin = −0.83 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.3445 (4)	0.9344 (3)	0.0139 (7)	0.0379 (16)
C2	0.3704 (4)	0.9545 (4)	0.1675 (7)	0.0380 (16)
C3	0.3159 (4)	0.9341 (4)	0.2826 (7)	0.0436 (17)
C4	0.2426 (4)	0.8974 (4)	0.2415 (8)	0.0501 (19)
H4	0.2070	0.8847	0.3153	0.060*
C5	0.2164 (4)	0.8770 (4)	0.0923 (8)	0.0448 (18)
C6	0.2673 (4)	0.8952 (4)	−0.0152 (7)	0.0452 (18)
H6	0.2511	0.8814	−0.1119	0.054*
C7	0.3419 (4)	0.9576 (4)	0.4425 (8)	0.054 (2)
C8	0.3909 (5)	0.9239 (5)	0.4971 (9)	0.073 (3)
H8A	0.4359	0.9444	0.4398	0.109*
H8B	0.3635	0.8707	0.4855	0.109*
H8C	0.4032	0.9361	0.5993	0.109*
C9	0.3867 (5)	1.0410 (4)	0.4567 (9)	0.075 (3)
H9A	0.4009	1.0542	0.5580	0.113*
H9B	0.3572	1.0623	0.4246	0.113*
H9C	0.4307	1.0599	0.3966	0.113*
C10	0.2728 (5)	0.9283 (6)	0.5465 (9)	0.093 (3)
H10A	0.2892	0.9381	0.6473	0.140*
H10B	0.2412	0.8755	0.5326	0.140*
H10C	0.2454	0.9532	0.5235	0.140*
C11	0.1325 (4)	0.8371 (4)	0.0622 (8)	0.0504 (19)
C12	0.0919 (5)	0.7706 (5)	0.1644 (13)	0.093 (3)
H12A	0.1089	0.7855	0.2639	0.140*
H12B	0.1020	0.7319	0.1348	0.140*
H12C	0.0392	0.7522	0.1593	0.140*
C13	0.1136 (5)	0.8131 (7)	−0.0941 (11)	0.111 (4)
H13A	0.1386	0.8557	−0.1577	0.166*
H13B	0.0607	0.7901	−0.1079	0.166*
H13C	0.1295	0.7779	−0.1176	0.166*
C14	0.1050 (5)	0.8924 (5)	0.0996 (15)	0.108 (4)
H14A	0.1138	0.9056	0.2022	0.162*
H14B	0.0525	0.8694	0.0793	0.162*
H14C	0.1316	0.9366	0.0405	0.162*
C15	0.4763 (4)	0.8597 (4)	0.1662 (9)	0.055 (2)
H15	0.4794	0.8896	0.2457	0.065*
C16	0.4667 (4)	0.7907 (5)	0.1946 (9)	0.058 (2)
C17	0.4623 (4)	0.7457 (5)	0.0802 (11)	0.067 (2)
H17	0.4559	0.6984	0.0963	0.081*
C18	0.4680 (4)	0.7741 (4)	−0.0626 (10)	0.059 (2)
C19	0.4772 (4)	0.8435 (4)	−0.0800 (10)	0.057 (2)
H19	0.4807	0.8617	−0.1754	0.068*
O1	0.3954 (2)	0.9530 (2)	−0.0863 (5)	0.0445 (12)
O2	0.4411 (2)	0.9891 (2)	0.1892 (5)	0.0430 (11)
Br1	0.46587 (7)	0.71757 (6)	−0.22749 (12)	0.0935 (5)
Br2	0.46210 (7)	0.75904 (6)	0.39099 (12)	0.0991 (5)
Co1	0.5000	1.0000	0.0000	0.0397 (4)
N1	0.4813 (3)	0.8862 (3)	0.0320 (7)	0.0498 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.041 (4)	0.028 (4)	0.039 (4)	0.013 (3)	0.008 (3)	0.009 (3)
C2	0.044 (5)	0.030 (4)	0.036 (4)	0.016 (3)	0.007 (3)	0.004 (3)
C3	0.049 (5)	0.034 (4)	0.039 (4)	0.014 (4)	0.010 (3)	0.004 (3)
C4	0.042 (5)	0.053 (5)	0.053 (5)	0.022 (4)	0.007 (3)	−0.004 (4)
C5	0.032 (4)	0.041 (4)	0.051 (5)	0.010 (3)	−0.001 (3)	0.002 (3)
C6	0.047 (5)	0.053 (5)	0.029 (4)	0.020 (4)	−0.007 (3)	0.001 (3)
C7	0.047 (5)	0.064 (5)	0.036 (4)	0.017 (4)	0.010 (3)	−0.006 (4)
C8	0.079 (6)	0.075 (6)	0.055 (6)	0.031 (5)	−0.006 (4)	0.000 (4)
C9	0.090 (7)	0.058 (6)	0.054 (6)	0.019 (5)	0.000 (5)	−0.015 (4)
C10	0.067 (6)	0.135 (9)	0.040 (5)	0.022 (6)	0.013 (4)	−0.008 (5)
C11	0.033 (4)	0.047 (5)	0.059 (5)	0.012 (4)	0.003 (3)	0.009 (4)
C12	0.041 (5)	0.070 (7)	0.136 (10)	0.003 (5)	−0.007 (5)	0.020 (6)
C13	0.034 (5)	0.172 (11)	0.088 (8)	0.022 (6)	−0.016 (5)	−0.031 (7)
C14	0.054 (6)	0.072 (7)	0.205 (13)	0.037 (6)	−0.015 (7)	−0.018 (7)
C15	0.040 (5)	0.057 (5)	0.063 (5)	0.021 (4)	−0.001 (4)	0.004 (4)
C16	0.066 (6)	0.051 (5)	0.061 (6)	0.032 (5)	0.004 (4)	0.017 (4)
C17	0.062 (6)	0.049 (5)	0.092 (7)	0.029 (5)	−0.001 (5)	0.010 (5)
C18	0.048 (5)	0.047 (5)	0.085 (7)	0.026 (4)	−0.014 (4)	−0.010 (4)
C19	0.046 (5)	0.050 (5)	0.069 (6)	0.020 (4)	−0.004 (4)	0.006 (4)
O1	0.040 (3)	0.048 (3)	0.035 (3)	0.014 (2)	0.004 (2)	0.004 (2)
O2	0.034 (3)	0.038 (3)	0.047 (3)	0.010 (2)	−0.007 (2)	−0.003 (2)
Br1	0.1267 (10)	0.0734 (7)	0.0889 (8)	0.0565 (7)	−0.0076 (6)	−0.0155 (5)
Br2	0.1300 (10)	0.0964 (9)	0.0811 (8)	0.0642 (8)	0.0057 (6)	0.0357 (6)
Co1	0.0329 (8)	0.0354 (8)	0.0443 (8)	0.0122 (6)	0.0033 (6)	0.0048 (6)
N1	0.047 (4)	0.037 (4)	0.058 (4)	0.016 (3)	−0.004 (3)	0.005 (3)

Geometric parameters (Å, º)

C1—O1	1.294 (7)	C12—H12A	0.9600
C1—C6	1.408 (9)	C12—H12B	0.9600
C1—C2	1.474 (9)	C12—H12C	0.9600
C2—O2	1.282 (8)	C13—H13A	0.9600
C2—C3	1.436 (9)	C13—H13B	0.9600
C3—C4	1.366 (9)	C13—H13C	0.9600
C3—C7	1.537 (9)	C14—H14A	0.9600
C4—C5	1.438 (10)	C14—H14B	0.9600
C4—H4	0.9300	C14—H14C	0.9600
C5—C6	1.343 (9)	C15—N1	1.315 (9)
C5—C11	1.529 (9)	C15—C16	1.365 (10)
C6—H6	0.9300	C15—H15	0.9300
C7—C9	1.501 (11)	C16—C17	1.365 (11)
C7—C10	1.559 (10)	C16—Br2	1.881 (8)
C7—C8	1.569 (12)	C17—C18	1.402 (11)
C8—H8A	0.9600	C17—H17	0.9300
C8—H8B	0.9600	C18—C19	1.359 (10)
C8—H8C	0.9600	C18—Br1	1.884 (9)
C9—H9A	0.9600	C19—N1	1.320 (10)
C9—H9B	0.9600	C19—H19	0.9300
C9—H9C	0.9600	O1—Co1	2.033 (4)
C10—H10A	0.9600	O2—Co1	2.049 (4)
C10—H10B	0.9600	Co1—O1^i	2.033 (4)
C10—H10C	0.9600	Co1—O2^i	2.049 (5)
C11—C13	1.486 (12)	Co1—N1^i	2.206 (6)
C11—C12	1.517 (11)	Co1—N1	2.206 (6)
C11—C14	1.548 (11)
O1—C1—C6	124.0 (6)	C11—C12—H12C	109.5
O1—C1—C2	116.8 (6)	H12A—C12—H12C	109.5
C6—C1—C2	119.1 (6)	H12B—C12—H12C	109.5
O2—C2—C3	124.2 (6)	C11—C13—H13A	109.5
O2—C2—C1	117.0 (6)	C11—C13—H13B	109.5
C3—C2—C1	118.8 (6)	H13A—C13—H13B	109.5
C4—C3—C2	117.1 (6)	C11—C13—H13C	109.5
C4—C3—C7	123.3 (6)	H13A—C13—H13C	109.5
C2—C3—C7	119.5 (6)	H13B—C13—H13C	109.5
C3—C4—C5	124.8 (7)	C11—C14—H14A	109.5
C3—C4—H4	117.6	C11—C14—H14B	109.5
C5—C4—H4	117.6	H14A—C14—H14B	109.5
C6—C5—C4	118.1 (6)	C11—C14—H14C	109.5
C6—C5—C11	122.8 (7)	H14A—C14—H14C	109.5
C4—C5—C11	119.0 (6)	H14B—C14—H14C	109.5
C5—C6—C1	122.1 (6)	N1—C15—C16	123.3 (8)
C5—C6—H6	119.0	N1—C15—H15	118.3
C1—C6—H6	119.0	C16—C15—H15	118.3
C9—C7—C3	111.2 (6)	C17—C16—C15	119.8 (8)
C9—C7—C10	108.3 (7)	C17—C16—Br2	120.4 (6)
C3—C7—C10	109.7 (6)	C15—C16—Br2	119.8 (7)
C9—C7—C8	108.6 (7)	C16—C17—C18	116.8 (8)
C3—C7—C8	111.0 (6)	C16—C17—H17	121.6
C10—C7—C8	107.9 (7)	C18—C17—H17	121.6
C7—C8—H8A	109.5	C19—C18—C17	119.3 (8)
C7—C8—H8B	109.5	C19—C18—Br1	120.7 (7)
H8A—C8—H8B	109.5	C17—C18—Br1	120.0 (6)
C7—C8—H8C	109.5	N1—C19—C18	123.0 (8)
H8A—C8—H8C	109.5	N1—C19—H19	118.5
H8B—C8—H8C	109.5	C18—C19—H19	118.5
C7—C9—H9A	109.5	C1—O1—Co1	112.7 (4)
C7—C9—H9B	109.5	C2—O2—Co1	112.5 (4)
H9A—C9—H9B	109.5	O1^i—Co1—O1	180.0
C7—C9—H9C	109.5	O1^i—Co1—O2	99.37 (18)
H9A—C9—H9C	109.5	O1—Co1—O2	80.63 (18)
H9B—C9—H9C	109.5	O1^i—Co1—O2^i	80.63 (18)
C7—C10—H10A	109.5	O1—Co1—O2^i	99.37 (18)
C7—C10—H10B	109.5	O2—Co1—O2^i	180.0
H10A—C10—H10B	109.5	O1^i—Co1—N1^i	87.9 (2)
C7—C10—H10C	109.5	O1—Co1—N1^i	92.1 (2)
H10A—C10—H10C	109.5	O2—Co1—N1^i	90.3 (2)
H10B—C10—H10C	109.5	O2^i—Co1—N1^i	89.7 (2)
C13—C11—C12	110.1 (8)	O1^i—Co1—N1	92.1 (2)
C13—C11—C5	112.8 (6)	O1—Co1—N1	87.9 (2)
C12—C11—C5	110.2 (6)	O2—Co1—N1	89.7 (2)
C13—C11—C14	108.9 (8)	O2^i—Co1—N1	90.3 (2)
C12—C11—C14	107.2 (8)	N1^i—Co1—N1	180.0
C5—C11—C14	107.4 (6)	C15—N1—C19	117.8 (7)
C11—C12—H12A	109.5	C15—N1—Co1	120.1 (5)
C11—C12—H12B	109.5	C19—N1—Co1	122.1 (5)
H12A—C12—H12B	109.5
O1—C1—C2—O2	0.6 (8)	C6—C5—C11—C13	6.8 (11)
C6—C1—C2—O2	178.9 (6)	C4—C5—C11—C13	−174.3 (8)
O1—C1—C2—C3	−179.2 (6)	C6—C5—C11—C12	130.3 (8)
C6—C1—C2—C3	−0.8 (9)	C4—C5—C11—C12	−50.9 (10)
O2—C2—C3—C4	179.9 (6)	C6—C5—C11—C14	−113.2 (9)
C1—C2—C3—C4	−0.4 (9)	C4—C5—C11—C14	65.6 (9)
O2—C2—C3—C7	3.0 (10)	N1—C15—C16—C17	0.4 (12)
C1—C2—C3—C7	−177.3 (6)	N1—C15—C16—Br2	178.8 (6)
C2—C3—C4—C5	0.9 (11)	C15—C16—C17—C18	−0.1 (12)
C7—C3—C4—C5	177.6 (7)	Br2—C16—C17—C18	−178.5 (6)
C3—C4—C5—C6	−0.1 (11)	C16—C17—C18—C19	−0.2 (11)
C3—C4—C5—C11	−179.0 (7)	C16—C17—C18—Br1	178.0 (6)
C4—C5—C6—C1	−1.3 (11)	C17—C18—C19—N1	0.2 (12)
C11—C5—C6—C1	177.6 (6)	Br1—C18—C19—N1	−177.9 (5)
O1—C1—C6—C5	179.9 (7)	C6—C1—O1—Co1	−174.3 (5)
C2—C1—C6—C5	1.8 (10)	C2—C1—O1—Co1	3.9 (7)
C4—C3—C7—C9	−115.8 (8)	C3—C2—O2—Co1	175.0 (5)
C2—C3—C7—C9	60.8 (9)	C1—C2—O2—Co1	−4.7 (7)
C4—C3—C7—C10	4.0 (11)	C16—C15—N1—C19	−0.4 (11)
C2—C3—C7—C10	−179.4 (7)	C16—C15—N1—Co1	−178.2 (6)
C4—C3—C7—C8	123.2 (8)	C18—C19—N1—C15	0.0 (11)
C2—C3—C7—C8	−60.2 (8)	C18—C19—N1—Co1	177.9 (6)

Symmetry code: (i) −x+1, −y+2, −z.

(2S_100K)

Crystal data

C38H46Cl4CoN2O4	Dx = 1.284 Mg m^−3
Mr = 795.50	Ag Kα radiation, λ = 0.56085 Å
Trigonal, P3	Cell parameters from 25871 reflections
a = 20.0094 (13) Å	θ = 0.9–20.6°
c = 8.8987 (7) Å	µ = 0.37 mm^−1
V = 3085.5 (5) Å^3	T = 100 K
Z = 3	Block, blue
F(000) = 1245	0.18 × 0.16 × 0.10 mm

Data collection

Bruker Kappa APEX II CCD detector diffractometer	4265 independent reflections
Radiation source: Bruker, Kappa Apex II	2901 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.142
φ and ω scans	θmax = 20.6°, θmin = 0.9°
Absorption correction: multi-scan Bruker AXS, 2008	h = −24→25
Tmin = 0.936, Tmax = 0.964	k = −25→24
25871 measured reflections	l = −11→11

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.095	H-atom parameters constrained
wR(F^2) = 0.256	w = 1/[σ^2(Fo^2) + (0.1029P)^2 + 14.8759P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
4265 reflections	Δρmax = 0.99 e Å^−3
229 parameters	Δρmin = −0.87 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.0686 (3)	0.4163 (3)	0.5105 (6)	0.0156 (12)
C2	0.0479 (3)	0.4213 (3)	0.6647 (6)	0.0149 (12)
C3	0.0694 (3)	0.3871 (3)	0.7808 (7)	0.0174 (12)
C4	0.1089 (3)	0.3494 (3)	0.7387 (7)	0.0207 (13)
H4	0.1235	0.3260	0.8152	0.025*
C5	0.1285 (3)	0.3437 (3)	0.5892 (7)	0.0188 (13)
C6	0.1099 (3)	0.3781 (3)	0.4761 (7)	0.0189 (12)
H6	0.1247	0.3762	0.3755	0.023*
C7	0.0477 (4)	0.3914 (4)	0.9452 (7)	0.0216 (13)
C8	−0.0411 (3)	0.3487 (4)	0.9594 (8)	0.0249 (14)
H8A	−0.0556	0.3429	1.0658	0.037*
H8B	−0.0630	0.2976	0.9128	0.037*
H8C	−0.0612	0.3785	0.9084	0.037*
C9	0.0817 (4)	0.4742 (4)	0.9968 (7)	0.0221 (14)
H9A	0.0712	0.4751	1.1042	0.033*
H9B	0.0584	0.4992	0.9398	0.033*
H9C	0.1376	0.5018	0.9800	0.033*
C10	0.0767 (4)	0.3511 (4)	1.0504 (8)	0.0298 (16)
H10A	0.1328	0.3750	1.0406	0.045*
H10B	0.0522	0.2963	1.0238	0.045*
H10C	0.0637	0.3561	1.1544	0.045*
C11	0.1667 (4)	0.2947 (4)	0.5555 (8)	0.0250 (14)
C12	0.2327 (5)	0.3143 (6)	0.6652 (10)	0.050 (2)
H12A	0.2725	0.3686	0.6532	0.076*
H12B	0.2551	0.2815	0.6443	0.076*
H12C	0.2130	0.3054	0.7684	0.076*
C13	0.2009 (7)	0.3093 (7)	0.4008 (10)	0.071 (3)
H13A	0.2273	0.3648	0.3795	0.107*
H13B	0.1597	0.2817	0.3270	0.107*
H13C	0.2379	0.2910	0.3949	0.107*
C14	0.1064 (5)	0.2127 (5)	0.5750 (17)	0.087 (5)
H14A	0.1309	0.1820	0.5983	0.130*
H14B	0.0766	0.1936	0.4819	0.130*
H14C	0.0720	0.2082	0.6575	0.130*
C15	−0.1484 (3)	0.3767 (4)	0.5940 (7)	0.0223 (14)
H15	−0.1298	0.3961	0.6918	0.027*
C16	−0.2218 (4)	0.3123 (4)	0.5764 (7)	0.0259 (14)
C17	−0.2514 (4)	0.2852 (4)	0.4330 (7)	0.0259 (14)
H17	−0.3015	0.2419	0.4190	0.031*
C18	−0.2057 (4)	0.3230 (4)	0.3156 (8)	0.0256 (14)
C19	−0.1315 (4)	0.3858 (4)	0.3359 (7)	0.0230 (14)
H19	−0.1001	0.4108	0.2508	0.028*
N1	−0.1041 (3)	0.4112 (3)	0.4741 (6)	0.0177 (11)
O1	0.0459 (2)	0.4482 (2)	0.4080 (5)	0.0187 (9)
O2	0.0100 (2)	0.4584 (2)	0.6835 (5)	0.0169 (9)
Cl1	−0.23703 (11)	0.29540 (11)	0.1328 (2)	0.0393 (5)
Cl2	−0.27400 (10)	0.26654 (11)	0.7347 (2)	0.0365 (5)
Co1	0.0000	0.5000	0.5000	0.0143 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.012 (3)	0.021 (3)	0.014 (3)	0.008 (2)	0.000 (2)	−0.002 (2)
C2	0.012 (3)	0.021 (3)	0.013 (3)	0.009 (2)	0.000 (2)	−0.002 (2)
C3	0.018 (3)	0.024 (3)	0.012 (3)	0.011 (3)	0.000 (2)	0.001 (2)
C4	0.025 (3)	0.023 (3)	0.018 (3)	0.014 (3)	−0.005 (2)	0.000 (2)
C5	0.018 (3)	0.022 (3)	0.024 (3)	0.015 (3)	−0.005 (2)	−0.007 (2)
C6	0.021 (3)	0.019 (3)	0.012 (3)	0.008 (3)	−0.002 (2)	−0.004 (2)
C7	0.030 (3)	0.036 (4)	0.007 (3)	0.022 (3)	0.002 (2)	−0.002 (2)
C8	0.017 (3)	0.027 (3)	0.029 (4)	0.010 (3)	0.003 (3)	0.002 (3)
C9	0.023 (3)	0.035 (4)	0.011 (3)	0.016 (3)	0.000 (2)	−0.006 (3)
C10	0.039 (4)	0.044 (4)	0.016 (3)	0.028 (4)	0.002 (3)	0.005 (3)
C11	0.026 (3)	0.028 (4)	0.029 (4)	0.020 (3)	−0.004 (3)	−0.006 (3)
C12	0.052 (5)	0.083 (7)	0.046 (5)	0.056 (5)	−0.014 (4)	−0.017 (5)
C13	0.127 (9)	0.117 (9)	0.038 (5)	0.112 (8)	0.030 (6)	0.015 (5)
C14	0.040 (5)	0.033 (5)	0.184 (15)	0.017 (4)	0.017 (7)	−0.031 (7)
C15	0.018 (3)	0.027 (3)	0.021 (3)	0.011 (3)	−0.001 (2)	−0.002 (3)
C16	0.025 (3)	0.038 (4)	0.019 (3)	0.019 (3)	0.003 (3)	0.000 (3)
C17	0.028 (3)	0.028 (4)	0.020 (3)	0.013 (3)	−0.009 (3)	−0.005 (3)
C18	0.027 (3)	0.028 (3)	0.019 (3)	0.012 (3)	−0.008 (3)	−0.008 (3)
C19	0.028 (3)	0.020 (3)	0.020 (3)	0.012 (3)	−0.003 (3)	−0.001 (2)
N1	0.024 (3)	0.020 (3)	0.014 (3)	0.013 (2)	0.002 (2)	0.000 (2)
O1	0.022 (2)	0.025 (2)	0.015 (2)	0.0161 (19)	−0.0007 (17)	−0.0008 (17)
O2	0.017 (2)	0.025 (2)	0.013 (2)	0.0134 (18)	0.0018 (16)	0.0014 (16)
Cl1	0.0418 (11)	0.0387 (10)	0.0229 (9)	0.0094 (8)	−0.0097 (7)	−0.0079 (7)
Cl2	0.0282 (9)	0.0425 (10)	0.0273 (10)	0.0089 (8)	0.0059 (7)	0.0074 (8)
Co1	0.0154 (6)	0.0184 (6)	0.0106 (6)	0.0096 (5)	−0.0010 (4)	−0.0005 (4)

Geometric parameters (Å, º)

C1—O1	1.318 (7)	C11—C12	1.528 (10)
C1—C6	1.412 (8)	C15—N1	1.338 (8)
C1—C2	1.452 (8)	C15—C16	1.395 (9)
C2—O2	1.309 (7)	C16—C17	1.398 (9)
C2—C3	1.419 (8)	C16—Cl2	1.719 (7)
C3—C4	1.391 (8)	C17—C18	1.344 (10)
C3—C7	1.541 (8)	C18—C19	1.397 (9)
C4—C5	1.408 (9)	C18—Cl1	1.731 (7)
C5—C6	1.370 (9)	C19—N1	1.338 (8)
C5—C11	1.544 (8)	N1—Co1	1.962 (5)
C7—C9	1.513 (9)	O1—Co1	1.881 (4)
C7—C10	1.528 (9)	O2—Co1	1.889 (4)
C7—C8	1.545 (9)	Co1—O1^i	1.881 (4)
C11—C14	1.483 (11)	Co1—O2^i	1.889 (4)
C11—C13	1.499 (11)	Co1—N1^i	1.962 (5)
O1—C1—C6	123.4 (5)	C15—C16—Cl2	118.6 (5)
O1—C1—C2	116.2 (5)	C17—C16—Cl2	121.0 (5)
C6—C1—C2	120.4 (5)	C18—C17—C16	117.0 (6)
O2—C2—C3	125.5 (5)	C17—C18—C19	121.6 (6)
O2—C2—C1	115.2 (5)	C17—C18—Cl1	121.0 (5)
C3—C2—C1	119.3 (5)	C19—C18—Cl1	117.5 (5)
C4—C3—C2	117.2 (5)	N1—C19—C18	120.6 (6)
C4—C3—C7	122.6 (5)	C15—N1—C19	119.8 (5)
C2—C3—C7	120.2 (5)	C15—N1—Co1	120.2 (4)
C3—C4—C5	123.7 (5)	C19—N1—Co1	120.0 (4)
C6—C5—C4	119.8 (5)	C1—O1—Co1	110.3 (4)
C6—C5—C11	121.4 (6)	C2—O2—Co1	111.0 (3)
C4—C5—C11	118.7 (5)	O1—Co1—O1^i	180.0
C5—C6—C1	119.5 (6)	O1—Co1—O2	86.84 (17)
C9—C7—C10	108.1 (5)	O1^i—Co1—O2	93.16 (17)
C9—C7—C3	111.4 (5)	O1—Co1—O2^i	93.16 (17)
C10—C7—C3	111.1 (5)	O1^i—Co1—O2^i	86.84 (17)
C9—C7—C8	110.2 (5)	O2—Co1—O2^i	180.0
C10—C7—C8	107.1 (5)	O1—Co1—N1^i	87.76 (18)
C3—C7—C8	108.9 (5)	O1^i—Co1—N1^i	92.24 (18)
C14—C11—C13	111.2 (8)	O2—Co1—N1^i	89.96 (19)
C14—C11—C12	109.2 (8)	O2^i—Co1—N1^i	90.04 (19)
C13—C11—C12	106.6 (7)	O1—Co1—N1	92.24 (18)
C14—C11—C5	107.1 (6)	O1^i—Co1—N1	87.76 (19)
C13—C11—C5	112.1 (6)	O2—Co1—N1	90.04 (19)
C12—C11—C5	110.7 (5)	O2^i—Co1—N1	89.96 (19)
N1—C15—C16	120.5 (6)	N1^i—Co1—N1	180.0
C15—C16—C17	120.4 (6)
O1—C1—C2—O2	−1.1 (7)	C6—C5—C11—C12	135.9 (7)
C6—C1—C2—O2	179.7 (5)	C4—C5—C11—C12	−47.5 (8)
O1—C1—C2—C3	179.0 (5)	N1—C15—C16—C17	−2.9 (10)
C6—C1—C2—C3	−0.3 (8)	N1—C15—C16—Cl2	176.0 (5)
O2—C2—C3—C4	179.3 (5)	C15—C16—C17—C18	0.9 (10)
C1—C2—C3—C4	−0.8 (8)	Cl2—C16—C17—C18	−178.0 (5)
O2—C2—C3—C7	0.4 (9)	C16—C17—C18—C19	1.2 (10)
C1—C2—C3—C7	−179.7 (5)	C16—C17—C18—Cl1	−178.9 (5)
C2—C3—C4—C5	0.2 (9)	C17—C18—C19—N1	−1.4 (10)
C7—C3—C4—C5	179.1 (6)	Cl1—C18—C19—N1	178.8 (5)
C3—C4—C5—C6	1.4 (9)	C16—C15—N1—C19	2.8 (9)
C3—C4—C5—C11	−175.2 (6)	C16—C15—N1—Co1	−178.5 (5)
C4—C5—C6—C1	−2.4 (9)	C18—C19—N1—C15	−0.7 (9)
C11—C5—C6—C1	174.1 (5)	C18—C19—N1—Co1	−179.5 (5)
O1—C1—C6—C5	−177.3 (5)	C6—C1—O1—Co1	−175.4 (4)
C2—C1—C6—C5	1.9 (8)	C2—C1—O1—Co1	5.4 (6)
C4—C3—C7—C9	121.8 (6)	C3—C2—O2—Co1	176.1 (5)
C2—C3—C7—C9	−59.3 (7)	C1—C2—O2—Co1	−3.8 (6)
C4—C3—C7—C10	1.2 (8)	C1—O1—Co1—O2	−6.0 (4)
C2—C3—C7—C10	−179.9 (6)	C1—O1—Co1—O2^i	174.0 (4)
C4—C3—C7—C8	−116.5 (6)	C1—O1—Co1—N1^i	84.1 (4)
C2—C3—C7—C8	62.4 (7)	C1—O1—Co1—N1	−95.9 (4)
C6—C5—C11—C14	−105.2 (9)	C2—O2—Co1—O1	5.4 (4)
C4—C5—C11—C14	71.4 (9)	C2—O2—Co1—O1^i	−174.6 (4)
C6—C5—C11—C13	17.0 (10)	C2—O2—Co1—N1^i	−82.3 (4)
C4—C5—C11—C13	−166.4 (7)	C2—O2—Co1—N1	97.7 (4)

Symmetry code: (i) −x, −y+1, −z+1.

(2S_150K)

Crystal data

C38H46Cl4CoN2O4	Dx = 1.261 Mg m^−3
Mr = 795.50	Ag Kα radiation, λ = 0.56085 Å
Trigonal, P3	Cell parameters from 9956 reflections
a = 20.166 (3) Å	θ = 0.9–21.1°
c = 8.9271 (10) Å	µ = 0.37 mm^−1
V = 3143.9 (9) Å^3	T = 150 K
Z = 3	Block, blue
F(000) = 1245	0.18 × 0.16 × 0.10 mm

Data collection

Bruker Kappa APEX II CCD detector diffractometer	4641 independent reflections
Radiation source: Bruker, Kappa Apex II	2214 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.108
φ and ω scans	θmax = 21.2°, θmin = 0.9°
Absorption correction: multi-scan Bruker AXS, 2008	h = −25→16
Tmin = 0.937, Tmax = 0.964	k = −21→25
9956 measured reflections	l = −11→8

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.106	H-atom parameters constrained
wR(F^2) = 0.313	w = 1/[σ^2(Fo^2) + (0.1421P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
4641 reflections	Δρmax = 0.67 e Å^−3
229 parameters	Δρmin = −0.93 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.5848 (4)	0.9317 (4)	0.9862 (7)	0.0210 (15)
C2	0.5799 (4)	0.9520 (4)	0.8348 (7)	0.0198 (14)
C3	0.6145 (4)	0.9304 (4)	0.7172 (7)	0.0261 (16)
C4	0.6521 (4)	0.8931 (4)	0.7599 (8)	0.0300 (17)
H4	0.6768	0.8800	0.6846	0.036*
C5	0.6566 (4)	0.8728 (4)	0.9083 (8)	0.0258 (16)
C6	0.6234 (4)	0.8907 (4)	1.0218 (8)	0.0270 (17)
H6	0.6258	0.8763	1.1220	0.032*
C7	0.6101 (4)	0.9532 (4)	0.5558 (8)	0.0302 (17)
C8	0.5280 (5)	0.9198 (5)	0.5029 (8)	0.0339 (18)
H8A	0.5001	0.8644	0.5209	0.051*
H8B	0.5275	0.9297	0.3956	0.051*
H8C	0.5034	0.9437	0.5582	0.051*
C9	0.6510 (5)	1.0408 (4)	0.5410 (8)	0.0375 (19)
H9A	0.6189	1.0597	0.5846	0.056*
H9B	0.6600	1.0550	0.4349	0.056*
H9C	0.7001	1.0636	0.5941	0.056*
C10	0.6494 (6)	0.9237 (6)	0.4488 (8)	0.048 (2)
H10A	0.7026	0.9437	0.4802	0.072*
H10B	0.6483	0.9410	0.3467	0.072*
H10C	0.6222	0.8676	0.4513	0.072*
C11	0.7053 (5)	0.8343 (4)	0.9420 (9)	0.0352 (19)
C12	0.6834 (7)	0.7660 (6)	0.8347 (11)	0.062 (3)
H12A	0.6915	0.7841	0.7308	0.094*
H12B	0.6294	0.7274	0.8493	0.094*
H12C	0.7154	0.7432	0.8562	0.094*
C13	0.6932 (8)	0.8022 (8)	1.1001 (12)	0.093 (5)
H13A	0.7009	0.7579	1.1013	0.140*
H13B	0.6410	0.7863	1.1329	0.140*
H13C	0.7300	0.8416	1.1681	0.140*
C14	0.7876 (6)	0.8932 (6)	0.9216 (16)	0.088 (4)
H14A	0.8114	0.9121	1.0198	0.131*
H14B	0.7915	0.9358	0.8622	0.131*
H14C	0.8141	0.8703	0.8695	0.131*
C15	0.3843 (4)	0.8647 (5)	0.8382 (8)	0.0351 (19)
H15	0.4098	0.8949	0.7529	0.042*
C16	0.3224 (5)	0.7927 (5)	0.8166 (9)	0.037 (2)
C17	0.2854 (5)	0.7482 (5)	0.9347 (8)	0.038 (2)
H17	0.2430	0.6982	0.9209	0.046*
C18	0.3106 (5)	0.7770 (5)	1.0767 (8)	0.0344 (19)
C19	0.3751 (5)	0.8502 (5)	1.0916 (7)	0.0316 (18)
H19	0.3943	0.8690	1.1889	0.038*
N1	0.4100 (3)	0.8938 (4)	0.9741 (6)	0.0302 (15)
O1	0.5535 (3)	0.9539 (3)	1.0912 (5)	0.0288 (12)
O2	0.5427 (3)	0.9893 (3)	0.8153 (5)	0.0245 (11)
Cl1	0.26496 (15)	0.72569 (13)	1.2345 (2)	0.0553 (7)
Cl2	0.29496 (15)	0.76135 (16)	0.6340 (2)	0.0643 (8)
Co1	0.5000	1.0000	1.0000	0.0192 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.026 (4)	0.017 (3)	0.016 (3)	0.008 (3)	−0.006 (3)	−0.008 (3)
C2	0.027 (4)	0.016 (3)	0.018 (3)	0.012 (3)	−0.001 (3)	0.000 (3)
C3	0.042 (5)	0.021 (4)	0.017 (3)	0.018 (4)	−0.001 (3)	0.000 (3)
C4	0.041 (5)	0.034 (4)	0.021 (4)	0.023 (4)	−0.001 (3)	−0.007 (3)
C5	0.031 (4)	0.024 (4)	0.026 (4)	0.017 (3)	−0.012 (3)	−0.010 (3)
C6	0.029 (4)	0.027 (4)	0.018 (3)	0.008 (3)	−0.003 (3)	0.000 (3)
C7	0.038 (5)	0.038 (5)	0.021 (3)	0.023 (4)	−0.002 (3)	0.000 (3)
C8	0.043 (5)	0.038 (5)	0.017 (4)	0.018 (4)	−0.005 (3)	−0.004 (3)
C9	0.046 (5)	0.031 (4)	0.031 (4)	0.016 (4)	0.002 (4)	0.003 (3)
C10	0.073 (7)	0.076 (7)	0.013 (4)	0.051 (6)	0.009 (4)	0.004 (4)
C11	0.049 (5)	0.031 (4)	0.036 (4)	0.028 (4)	−0.014 (4)	−0.004 (3)
C12	0.077 (8)	0.064 (7)	0.064 (7)	0.048 (6)	−0.006 (5)	−0.009 (5)
C13	0.131 (11)	0.163 (13)	0.059 (7)	0.128 (11)	0.034 (7)	0.061 (8)
C14	0.042 (6)	0.047 (7)	0.178 (14)	0.025 (6)	−0.019 (7)	0.013 (7)
C15	0.026 (4)	0.054 (5)	0.025 (4)	0.019 (4)	−0.002 (3)	−0.007 (4)
C16	0.036 (5)	0.051 (5)	0.034 (4)	0.028 (4)	−0.010 (4)	−0.013 (4)
C17	0.046 (5)	0.041 (5)	0.034 (4)	0.028 (4)	0.001 (4)	−0.016 (4)
C18	0.046 (5)	0.039 (5)	0.020 (4)	0.023 (4)	0.005 (3)	0.004 (3)
C19	0.048 (5)	0.042 (5)	0.013 (3)	0.029 (4)	0.004 (3)	0.005 (3)
N1	0.029 (4)	0.040 (4)	0.026 (3)	0.021 (3)	0.001 (3)	−0.004 (3)
O1	0.043 (3)	0.030 (3)	0.018 (2)	0.022 (3)	−0.002 (2)	−0.004 (2)
O2	0.031 (3)	0.025 (3)	0.017 (2)	0.013 (2)	0.002 (2)	0.0058 (19)
Cl1	0.0696 (17)	0.0427 (14)	0.0418 (12)	0.0190 (13)	0.0114 (11)	0.0094 (10)
Cl2	0.0551 (16)	0.0788 (19)	0.0369 (12)	0.0169 (14)	−0.0150 (11)	−0.0185 (12)
Co1	0.0234 (8)	0.0212 (7)	0.0140 (6)	0.0119 (6)	0.0000 (5)	−0.0015 (5)

Geometric parameters (Å, º)

C1—O1	1.326 (8)	C11—C12	1.550 (12)
C1—C6	1.427 (10)	C15—N1	1.335 (9)
C1—C2	1.430 (9)	C15—C16	1.375 (11)
C2—O2	1.313 (8)	C16—C17	1.343 (11)
C2—C3	1.444 (9)	C16—Cl2	1.736 (8)
C3—C4	1.362 (10)	C17—C18	1.380 (10)
C3—C7	1.528 (9)	C18—C19	1.404 (11)
C4—C5	1.402 (9)	C18—Cl1	1.717 (8)
C5—C6	1.358 (10)	C19—N1	1.322 (9)
C5—C11	1.558 (10)	N1—Co1	2.011 (6)
C7—C8	1.518 (11)	O1—Co1	1.921 (5)
C7—C9	1.537 (11)	O2—Co1	1.922 (4)
C7—C10	1.537 (10)	Co1—O1^i	1.921 (5)
C11—C14	1.492 (13)	Co1—O2^i	1.922 (4)
C11—C13	1.521 (12)	Co1—N1^i	2.011 (6)
O1—C1—C6	121.9 (6)	C17—C16—Cl2	121.7 (7)
O1—C1—C2	117.3 (6)	C15—C16—Cl2	118.1 (6)
C6—C1—C2	120.8 (6)	C16—C17—C18	118.4 (8)
O2—C2—C1	115.5 (6)	C17—C18—C19	118.7 (7)
O2—C2—C3	125.3 (6)	C17—C18—Cl1	121.8 (7)
C1—C2—C3	119.2 (6)	C19—C18—Cl1	119.5 (6)
C4—C3—C2	116.7 (6)	N1—C19—C18	122.0 (7)
C4—C3—C7	124.2 (6)	C19—N1—C15	117.9 (7)
C2—C3—C7	119.0 (6)	C19—N1—Co1	120.9 (5)
C3—C4—C5	124.0 (7)	C15—N1—Co1	121.2 (5)
C6—C5—C4	121.1 (7)	C1—O1—Co1	109.9 (4)
C6—C5—C11	120.4 (6)	C2—O2—Co1	111.5 (4)
C4—C5—C11	118.4 (6)	O1^i—Co1—O1	180.0
C5—C6—C1	118.2 (6)	O1^i—Co1—O2	94.70 (19)
C8—C7—C3	112.0 (6)	O1—Co1—O2	85.30 (19)
C8—C7—C9	108.8 (6)	O1^i—Co1—O2^i	85.30 (19)
C3—C7—C9	110.4 (6)	O1—Co1—O2^i	94.70 (19)
C8—C7—C10	107.0 (6)	O2—Co1—O2^i	180.0 (3)
C3—C7—C10	110.5 (6)	O1^i—Co1—N1^i	87.7 (2)
C9—C7—C10	107.9 (7)	O1—Co1—N1^i	92.3 (2)
C14—C11—C13	109.3 (9)	O2—Co1—N1^i	90.1 (2)
C14—C11—C12	110.0 (9)	O2^i—Co1—N1^i	89.9 (2)
C13—C11—C12	106.3 (8)	O1^i—Co1—N1	92.3 (2)
C14—C11—C5	107.9 (7)	O1—Co1—N1	87.7 (2)
C13—C11—C5	112.6 (7)	O2—Co1—N1	89.9 (2)
C12—C11—C5	110.7 (6)	O2^i—Co1—N1	90.1 (2)
N1—C15—C16	122.7 (7)	N1^i—Co1—N1	180.0
C17—C16—C15	120.2 (7)
O1—C1—C2—O2	−1.7 (9)	C6—C5—C11—C14	−105.8 (9)
C6—C1—C2—O2	179.7 (6)	C4—C5—C11—C14	70.0 (10)
O1—C1—C2—C3	178.7 (6)	C6—C5—C11—C13	14.9 (12)
C6—C1—C2—C3	0.1 (10)	C4—C5—C11—C13	−169.3 (9)
O2—C2—C3—C4	178.8 (7)	C6—C5—C11—C12	133.8 (8)
C1—C2—C3—C4	−1.7 (10)	C4—C5—C11—C12	−50.4 (10)
O2—C2—C3—C7	1.3 (11)	N1—C15—C16—C17	−0.5 (12)
C1—C2—C3—C7	−179.2 (6)	N1—C15—C16—Cl2	−179.7 (6)
C2—C3—C4—C5	2.2 (11)	C15—C16—C17—C18	0.7 (12)
C7—C3—C4—C5	179.4 (7)	Cl2—C16—C17—C18	179.9 (6)
C3—C4—C5—C6	−0.8 (12)	C16—C17—C18—C19	−2.1 (12)
C3—C4—C5—C11	−176.6 (7)	C16—C17—C18—Cl1	177.8 (6)
C4—C5—C6—C1	−0.9 (11)	C17—C18—C19—N1	3.5 (12)
C11—C5—C6—C1	174.8 (6)	Cl1—C18—C19—N1	−176.4 (6)
O1—C1—C6—C5	−177.3 (6)	C18—C19—N1—C15	−3.2 (11)
C2—C1—C6—C5	1.2 (10)	C18—C19—N1—Co1	177.7 (6)
C4—C3—C7—C8	122.8 (8)	C16—C15—N1—C19	1.7 (11)
C2—C3—C7—C8	−59.9 (9)	C16—C15—N1—Co1	−179.2 (6)
C4—C3—C7—C9	−115.7 (8)	C6—C1—O1—Co1	−175.5 (5)
C2—C3—C7—C9	61.5 (9)	C2—C1—O1—Co1	5.9 (7)
C4—C3—C7—C10	3.6 (11)	C1—C2—O2—Co1	−3.5 (7)
C2—C3—C7—C10	−179.2 (7)	C3—C2—O2—Co1	176.0 (6)

Symmetry code: (i) −x+1, −y+2, −z+2.

(2S_175K)

Crystal data

C38H46Cl4CoN2O4	Dx = 1.250 Mg m^−3
Mr = 795.50	Ag Kα radiation, λ = 0.56085 Å
Trigonal, P3	Cell parameters from 13452 reflections
a = 20.243 (5) Å	θ = 0.9–20.6°
c = 8.933 (5) Å	µ = 0.36 mm^−1
V = 3170 (2) Å^3	T = 175 K
Z = 3	Block, blue
F(000) = 1245	0.18 × 0.16 × 0.10 mm

Data collection

Bruker Kappa APEX II CCD detector diffractometer	4286 independent reflections
Radiation source: Bruker, Kappa Apex II	2085 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.130
φ and ω scans	θmax = 20.6°, θmin = 0.9°
Absorption correction: multi-scan Bruker AXS, 2008	h = −25→22
Tmin = 0.937, Tmax = 0.965	k = −19→24
13452 measured reflections	l = −10→11

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.105	w = 1/[σ^2(Fo^2) + (0.1396P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.307	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.64 e Å^−3
4286 reflections	Δρmin = −0.50 e Å^−3
230 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.022 (4)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.6544 (4)	0.0678 (4)	0.9859 (7)	0.0284 (15)
C2	0.6286 (4)	0.0476 (4)	0.8355 (7)	0.0303 (16)
C3	0.6848 (4)	0.0684 (4)	0.7170 (8)	0.0370 (18)
C4	0.7599 (4)	0.1061 (4)	0.7575 (8)	0.0369 (17)
H4	0.7972	0.1192	0.6813	0.044*
C5	0.7855 (4)	0.1270 (4)	0.9091 (8)	0.0375 (18)
C6	0.7339 (4)	0.1087 (4)	1.0185 (8)	0.0380 (18)
H6	0.7505	0.1232	1.1187	0.046*
C7	0.6571 (4)	0.0464 (4)	0.5532 (8)	0.0415 (19)
C8	0.6115 (5)	−0.0402 (5)	0.5373 (10)	0.054 (2)
H8A	0.6412	−0.0623	0.5775	0.080*
H8B	0.6004	−0.0537	0.4313	0.080*
H8C	0.5635	−0.0602	0.5929	0.080*
C9	0.6083 (5)	0.0797 (5)	0.5041 (9)	0.046 (2)
H9A	0.5600	0.0550	0.5593	0.069*
H9B	0.5981	0.0712	0.3966	0.069*
H9C	0.6353	0.1347	0.5247	0.069*
C10	0.7260 (5)	0.0748 (5)	0.4484 (9)	0.055 (2)
H10A	0.7584	0.1302	0.4587	0.083*
H10B	0.7083	0.0622	0.3447	0.083*
H10C	0.7555	0.0500	0.4749	0.083*
C11	0.8716 (4)	0.1655 (4)	0.9411 (9)	0.0426 (19)
C12	0.8968 (6)	0.1086 (6)	0.9115 (15)	0.088 (4)
H12A	0.9438	0.1326	0.8521	0.132*
H12B	0.8568	0.0651	0.8561	0.132*
H12C	0.9062	0.0907	1.0068	0.132*
C13	0.8910 (6)	0.1960 (8)	1.0951 (13)	0.104 (5)
H13A	0.9426	0.2405	1.0964	0.156*
H13B	0.8889	0.1566	1.1620	0.156*
H13C	0.8545	0.2112	1.1290	0.156*
C14	0.9150 (5)	0.2339 (6)	0.8340 (11)	0.069 (3)
H14A	0.9047	0.2748	0.8619	0.104*
H14B	0.8980	0.2177	0.7310	0.104*
H14C	0.9699	0.2528	0.8414	0.104*
C15	0.4745 (4)	−0.1525 (5)	0.9083 (10)	0.052 (2)
H15	0.4747	−0.1340	0.8105	0.063*
C16	0.4663 (5)	−0.2244 (5)	0.9261 (10)	0.049 (2)
C17	0.4623 (5)	−0.2543 (5)	1.0674 (11)	0.056 (2)
H17	0.4555	−0.3039	1.0809	0.067*
C18	0.4684 (5)	−0.2102 (5)	1.1841 (10)	0.053 (2)
C19	0.4789 (5)	−0.1363 (5)	1.1623 (10)	0.052 (2)
H19	0.4836	−0.1057	1.2466	0.062*
N1	0.4822 (3)	−0.1094 (4)	1.0259 (7)	0.0406 (16)
O1	0.6016 (3)	0.0467 (3)	1.0898 (5)	0.0377 (12)
O2	0.5547 (3)	0.0111 (3)	0.8133 (5)	0.0340 (12)
Cl1	0.46394 (18)	−0.24181 (18)	1.3656 (3)	0.0841 (10)
Cl2	0.46222 (16)	−0.27512 (14)	0.7660 (3)	0.0743 (8)
Co1	0.5000	0.0000	1.0000	0.0279 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.028 (4)	0.026 (4)	0.028 (4)	0.012 (3)	0.002 (3)	0.001 (3)
C2	0.033 (4)	0.030 (4)	0.019 (3)	0.010 (3)	−0.002 (3)	−0.007 (3)
C3	0.047 (5)	0.024 (4)	0.034 (4)	0.014 (4)	0.002 (3)	0.005 (3)
C4	0.042 (5)	0.030 (4)	0.033 (4)	0.013 (4)	0.001 (3)	0.004 (3)
C5	0.030 (4)	0.037 (4)	0.043 (4)	0.015 (4)	−0.002 (3)	0.003 (3)
C6	0.054 (5)	0.032 (4)	0.036 (4)	0.027 (4)	−0.008 (4)	−0.003 (3)
C7	0.039 (4)	0.045 (5)	0.026 (4)	0.010 (4)	0.001 (3)	−0.005 (3)
C8	0.065 (6)	0.044 (5)	0.043 (5)	0.021 (5)	0.007 (4)	−0.007 (4)
C9	0.050 (5)	0.040 (5)	0.037 (5)	0.015 (4)	−0.005 (4)	−0.002 (3)
C10	0.054 (5)	0.073 (6)	0.027 (4)	0.023 (5)	0.009 (4)	−0.010 (4)
C11	0.030 (4)	0.043 (5)	0.048 (5)	0.013 (4)	0.000 (3)	0.010 (4)
C12	0.060 (7)	0.066 (7)	0.152 (12)	0.041 (6)	−0.031 (7)	−0.016 (7)
C13	0.052 (6)	0.162 (13)	0.078 (8)	0.038 (7)	−0.032 (6)	−0.059 (8)
C14	0.044 (5)	0.069 (7)	0.074 (7)	0.013 (5)	−0.003 (5)	0.013 (5)
C15	0.038 (5)	0.046 (5)	0.057 (6)	0.010 (4)	−0.002 (4)	−0.010 (4)
C16	0.039 (5)	0.047 (5)	0.048 (5)	0.011 (4)	0.004 (4)	0.001 (4)
C17	0.054 (6)	0.052 (6)	0.059 (6)	0.025 (5)	0.009 (4)	0.008 (5)
C18	0.046 (5)	0.063 (6)	0.053 (5)	0.030 (5)	0.001 (4)	0.016 (5)
C19	0.054 (5)	0.075 (6)	0.044 (5)	0.045 (5)	0.003 (4)	0.003 (4)
N1	0.030 (3)	0.055 (4)	0.039 (4)	0.023 (3)	−0.003 (3)	−0.006 (3)
O1	0.036 (3)	0.040 (3)	0.030 (3)	0.014 (2)	−0.002 (2)	0.001 (2)
O2	0.031 (3)	0.033 (3)	0.030 (3)	0.010 (2)	−0.002 (2)	−0.003 (2)
Cl1	0.119 (2)	0.108 (2)	0.0568 (17)	0.080 (2)	0.0093 (15)	0.0267 (15)
Cl2	0.095 (2)	0.0584 (16)	0.0639 (17)	0.0336 (15)	−0.0008 (14)	−0.0120 (12)
Co1	0.0253 (8)	0.0286 (8)	0.0264 (7)	0.0109 (6)	0.0019 (5)	0.0012 (5)

Geometric parameters (Å, º)

C1—O1	1.315 (8)	C11—C14	1.545 (11)
C1—C6	1.424 (10)	C15—N1	1.324 (10)
C1—C2	1.425 (9)	C15—C16	1.389 (12)
C2—O2	1.311 (8)	C16—C17	1.385 (12)
C2—C3	1.454 (10)	C16—Cl2	1.738 (9)
C3—C4	1.364 (10)	C17—C18	1.337 (12)
C3—C7	1.550 (10)	C18—C19	1.415 (12)
C4—C5	1.437 (10)	C18—Cl1	1.729 (9)
C5—C6	1.340 (10)	C19—N1	1.323 (10)
C5—C11	1.540 (10)	N1—Co1	2.071 (7)
C7—C9	1.513 (12)	O1—Co1	1.955 (5)
C7—C8	1.526 (11)	O2—Co1	1.952 (5)
C7—C10	1.533 (11)	Co1—O2^i	1.952 (5)
C11—C13	1.478 (13)	Co1—O1^i	1.955 (5)
C11—C12	1.499 (13)	Co1—N1^i	2.071 (7)
O1—C1—C6	122.9 (6)	C17—C16—Cl2	121.1 (7)
O1—C1—C2	116.9 (6)	C15—C16—Cl2	118.0 (7)
C6—C1—C2	120.3 (6)	C18—C17—C16	116.9 (9)
O2—C2—C1	117.0 (6)	C17—C18—C19	120.9 (8)
O2—C2—C3	124.1 (6)	C17—C18—Cl1	120.9 (7)
C1—C2—C3	118.9 (6)	C19—C18—Cl1	118.2 (7)
C4—C3—C2	117.4 (6)	N1—C19—C18	120.8 (8)
C4—C3—C7	123.6 (7)	C19—N1—C15	119.6 (8)
C2—C3—C7	119.1 (6)	C19—N1—Co1	119.3 (6)
C3—C4—C5	123.5 (7)	C15—N1—Co1	121.1 (6)
C6—C5—C4	119.3 (7)	C1—O1—Co1	110.8 (4)
C6—C5—C11	122.3 (7)	C2—O2—Co1	111.0 (4)
C4—C5—C11	118.3 (7)	O2—Co1—O2^i	180.0
C5—C6—C1	120.6 (7)	O2—Co1—O1^i	95.97 (19)
C9—C7—C8	109.3 (7)	O2^i—Co1—O1^i	84.02 (19)
C9—C7—C10	109.3 (7)	O2—Co1—O1	84.03 (19)
C8—C7—C10	106.7 (7)	O2^i—Co1—O1	95.98 (19)
C9—C7—C3	111.7 (6)	O1^i—Co1—O1	180.0
C8—C7—C3	110.0 (6)	O2—Co1—N1^i	89.8 (2)
C10—C7—C3	109.7 (6)	O2^i—Co1—N1^i	90.2 (2)
C13—C11—C12	111.3 (9)	O1^i—Co1—N1^i	92.8 (2)
C13—C11—C5	112.4 (7)	O1—Co1—N1^i	87.2 (2)
C12—C11—C5	108.2 (7)	O2—Co1—N1	90.2 (2)
C13—C11—C14	106.8 (8)	O2^i—Co1—N1	89.8 (2)
C12—C11—C14	108.7 (8)	O1^i—Co1—N1	87.2 (2)
C5—C11—C14	109.4 (6)	O1—Co1—N1	92.8 (2)
N1—C15—C16	120.8 (9)	N1^i—Co1—N1	180.0
C17—C16—C15	120.8 (8)
O1—C1—C2—O2	1.3 (9)	C6—C5—C11—C13	−13.8 (12)
C6—C1—C2—O2	−178.9 (6)	C4—C5—C11—C13	169.9 (9)
O1—C1—C2—C3	−178.7 (6)	C6—C5—C11—C12	109.5 (9)
C6—C1—C2—C3	1.0 (10)	C4—C5—C11—C12	−66.8 (10)
O2—C2—C3—C4	−179.7 (7)	C6—C5—C11—C14	−132.3 (8)
C1—C2—C3—C4	0.4 (10)	C4—C5—C11—C14	51.5 (10)
O2—C2—C3—C7	−0.1 (10)	N1—C15—C16—C17	3.1 (13)
C1—C2—C3—C7	179.9 (6)	N1—C15—C16—Cl2	−176.3 (6)
C2—C3—C4—C5	−1.1 (11)	C15—C16—C17—C18	−1.4 (13)
C7—C3—C4—C5	179.4 (7)	Cl2—C16—C17—C18	177.9 (7)
C3—C4—C5—C6	0.3 (11)	C16—C17—C18—C19	−0.3 (13)
C3—C4—C5—C11	176.7 (7)	C16—C17—C18—Cl1	179.8 (6)
C4—C5—C6—C1	1.1 (11)	C17—C18—C19—N1	0.6 (13)
C11—C5—C6—C1	−175.1 (6)	Cl1—C18—C19—N1	−179.5 (6)
O1—C1—C6—C5	177.9 (7)	C18—C19—N1—C15	1.0 (11)
C2—C1—C6—C5	−1.8 (10)	C18—C19—N1—Co1	−178.7 (6)
C4—C3—C7—C9	−122.5 (8)	C16—C15—N1—C19	−2.8 (12)
C2—C3—C7—C9	58.0 (9)	C16—C15—N1—Co1	176.9 (6)
C4—C3—C7—C8	116.1 (8)	C6—C1—O1—Co1	175.0 (5)
C2—C3—C7—C8	−63.5 (9)	C2—C1—O1—Co1	−5.3 (7)
C4—C3—C7—C10	−1.1 (10)	C1—C2—O2—Co1	3.4 (7)
C2—C3—C7—C10	179.4 (7)	C3—C2—O2—Co1	−176.6 (6)

Symmetry code: (i) −x+1, −y, −z+2.

(2S_200K)

Crystal data

C38H46Cl4CoN2O4	Dx = 1.237 Mg m^−3
Mr = 795.50	Ag Kα radiation, λ = 0.56085 Å
Trigonal, P3	Cell parameters from 26508 reflections
a = 20.334 (5) Å	θ = 0.9–20.6°
c = 8.945 (5) Å	µ = 0.36 mm^−1
V = 3203 (2) Å^3	T = 200 K
Z = 3	Block, blue
F(000) = 1245	0.18 × 0.16 × 0.10 mm

Data collection

Bruker Kappa APEX II CCD detector diffractometer	4414 independent reflections
Radiation source: Bruker, Kappa Apex II	2591 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.142
φ and ω scans	θmax = 20.6°, θmin = 0.9°
Absorption correction: multi-scan Bruker AXS, 2008	h = −25→25
Tmin = 0.938, Tmax = 0.965	k = −25→25
26508 measured reflections	l = −11→8

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.093	H-atom parameters constrained
wR(F^2) = 0.273	w = 1/[σ^2(Fo^2) + (0.1318P)^2 + 4.8693P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
4414 reflections	Δρmax = 0.51 e Å^−3
229 parameters	Δρmin = −0.68 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Co1	0.5000	0.0000	1.0000	0.0268 (3)
Cl2	0.26017 (14)	−0.27676 (13)	1.2307 (3)	0.0805 (7)
Cl1	0.29372 (14)	−0.24450 (16)	0.6341 (3)	0.0896 (9)
O2	0.4545 (2)	0.0113 (2)	1.1891 (4)	0.0326 (9)
O1	0.4434 (2)	0.0477 (2)	0.9122 (4)	0.0345 (10)
N1	0.4064 (3)	−0.1120 (3)	0.9720 (6)	0.0375 (12)
C2	0.4176 (3)	0.0477 (3)	1.1675 (6)	0.0325 (13)
C3	0.3832 (3)	0.0684 (3)	1.2851 (6)	0.0312 (13)
C7	0.3884 (4)	0.0464 (4)	1.4475 (7)	0.0398 (15)
C4	0.3458 (4)	0.1049 (3)	1.2447 (7)	0.0362 (14)
H4	0.3216	0.1178	1.3210	0.043*
C11	0.2938 (4)	0.1650 (4)	1.0619 (8)	0.0418 (15)
C5	0.3401 (4)	0.1257 (3)	1.0926 (7)	0.0370 (14)
C1	0.4125 (3)	0.0678 (3)	1.0137 (6)	0.0278 (12)
C6	0.3744 (3)	0.1085 (3)	0.9824 (7)	0.0334 (13)
H6	0.3728	0.1238	0.8827	0.040*
C18	0.3206 (4)	−0.2123 (5)	0.8171 (9)	0.0539 (19)
C19	0.3824 (4)	−0.1404 (4)	0.8373 (7)	0.0445 (16)
H19	0.4083	−0.1107	0.7522	0.053*
C8	0.4702 (4)	0.0803 (4)	1.4955 (7)	0.0478 (17)
H8A	0.4971	0.1352	1.4774	0.072*
H8B	0.4943	0.0571	1.4380	0.072*
H8C	0.4722	0.0707	1.6022	0.072*
C16	0.3068 (4)	−0.2261 (4)	1.0735 (8)	0.0493 (17)
C17	0.2817 (4)	−0.2563 (4)	0.9341 (10)	0.059 (2)
H17	0.2390	−0.3056	0.9208	0.070*
C13	0.3026 (6)	0.1939 (6)	0.9046 (10)	0.085 (3)
H13A	0.2867	0.2320	0.8993	0.127*
H13B	0.2710	0.1516	0.8375	0.127*
H13C	0.3560	0.2169	0.8744	0.127*
C15	0.3696 (4)	−0.1544 (4)	1.0898 (8)	0.0452 (16)
H15	0.3867	−0.1350	1.1875	0.054*
C9	0.3472 (5)	−0.0400 (4)	1.4628 (8)	0.0536 (19)
H9A	0.3747	−0.0601	1.4064	0.080*
H9B	0.2955	−0.0618	1.4233	0.080*
H9C	0.3450	−0.0537	1.5685	0.080*
C10	0.3491 (5)	0.0749 (5)	1.5553 (8)	0.060 (2)
H10A	0.3490	0.0563	1.6564	0.090*
H10B	0.2966	0.0560	1.5225	0.090*
H10C	0.3765	0.1306	1.5556	0.090*
C14	0.3197 (5)	0.2346 (5)	1.1643 (10)	0.067 (2)
H14A	0.3216	0.2200	1.2681	0.101*
H14B	0.2838	0.2532	1.1565	0.101*
H14C	0.3703	0.2747	1.1337	0.101*
C12	0.2116 (4)	0.1095 (5)	1.0933 (12)	0.078 (3)
H12A	0.2071	0.0844	1.1893	0.117*
H12B	0.1910	0.0713	1.0136	0.117*
H12C	0.1831	0.1366	1.0973	0.117*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0321 (6)	0.0273 (6)	0.0245 (6)	0.0175 (5)	0.0001 (4)	−0.0012 (4)
Cl2	0.0882 (17)	0.0625 (14)	0.0709 (15)	0.0229 (12)	0.0167 (12)	0.0183 (11)
Cl1	0.0723 (15)	0.108 (2)	0.0639 (15)	0.0262 (14)	−0.0239 (12)	−0.0354 (13)
O2	0.041 (2)	0.038 (2)	0.028 (2)	0.027 (2)	−0.0027 (17)	0.0015 (17)
O1	0.042 (2)	0.041 (2)	0.026 (2)	0.024 (2)	−0.0003 (18)	−0.0013 (17)
N1	0.035 (3)	0.045 (3)	0.041 (3)	0.026 (3)	0.001 (2)	0.000 (2)
C2	0.044 (4)	0.029 (3)	0.026 (3)	0.019 (3)	−0.001 (3)	−0.001 (2)
C3	0.042 (3)	0.027 (3)	0.026 (3)	0.019 (3)	0.001 (2)	−0.004 (2)
C7	0.060 (4)	0.045 (4)	0.027 (3)	0.036 (3)	0.004 (3)	−0.003 (3)
C4	0.045 (4)	0.038 (3)	0.027 (3)	0.022 (3)	0.000 (3)	−0.005 (3)
C11	0.048 (4)	0.042 (4)	0.045 (4)	0.029 (3)	−0.010 (3)	−0.009 (3)
C5	0.044 (4)	0.030 (3)	0.042 (4)	0.023 (3)	−0.013 (3)	−0.007 (3)
C1	0.027 (3)	0.026 (3)	0.029 (3)	0.012 (2)	−0.003 (2)	−0.003 (2)
C6	0.035 (3)	0.030 (3)	0.032 (3)	0.014 (3)	−0.006 (3)	−0.005 (2)
C18	0.049 (4)	0.066 (5)	0.056 (5)	0.035 (4)	−0.016 (4)	−0.020 (4)
C19	0.037 (4)	0.060 (4)	0.037 (4)	0.024 (3)	0.002 (3)	−0.003 (3)
C8	0.066 (5)	0.052 (4)	0.030 (4)	0.033 (4)	−0.008 (3)	−0.001 (3)
C16	0.058 (5)	0.051 (4)	0.047 (4)	0.033 (4)	0.005 (3)	0.001 (3)
C17	0.052 (5)	0.052 (5)	0.071 (6)	0.025 (4)	−0.002 (4)	−0.015 (4)
C13	0.117 (8)	0.136 (9)	0.058 (5)	0.106 (8)	0.007 (5)	0.029 (5)
C15	0.052 (4)	0.042 (4)	0.044 (4)	0.026 (3)	0.006 (3)	0.004 (3)
C9	0.070 (5)	0.052 (4)	0.043 (4)	0.034 (4)	0.016 (4)	0.015 (3)
C10	0.101 (6)	0.074 (5)	0.030 (4)	0.062 (5)	0.015 (4)	0.006 (3)
C14	0.096 (7)	0.059 (5)	0.072 (6)	0.058 (5)	−0.021 (5)	−0.015 (4)
C12	0.042 (4)	0.054 (5)	0.137 (9)	0.024 (4)	−0.011 (5)	0.011 (5)

Geometric parameters (Å, º)

Co1—O2^i	1.995 (4)	C3—C7	1.539 (8)
Co1—O2	1.995 (4)	C7—C8	1.509 (10)
Co1—O1^i	2.000 (4)	C7—C9	1.530 (9)
Co1—O1	2.000 (4)	C7—C10	1.539 (9)
Co1—N1	2.130 (5)	C4—C5	1.446 (9)
Co1—N1^i	2.130 (5)	C11—C13	1.501 (10)
Cl2—C16	1.720 (8)	C11—C12	1.503 (10)
Cl1—C18	1.746 (8)	C11—C5	1.534 (8)
O2—C2	1.305 (7)	C11—C14	1.541 (10)
O1—C1	1.282 (7)	C5—C6	1.350 (9)
N1—C19	1.320 (8)	C1—C6	1.416 (8)
N1—C15	1.330 (8)	C18—C17	1.347 (11)
C2—C3	1.439 (8)	C18—C19	1.384 (10)
C2—C1	1.454 (8)	C16—C17	1.371 (11)
C3—C4	1.351 (8)	C16—C15	1.383 (10)
O2^i—Co1—O2	180.0	C9—C7—C3	109.9 (5)
O2^i—Co1—O1^i	82.24 (15)	C8—C7—C10	108.1 (6)
O2—Co1—O1^i	97.76 (15)	C9—C7—C10	106.7 (6)
O2^i—Co1—O1	97.76 (15)	C3—C7—C10	111.0 (5)
O2—Co1—O1	82.24 (15)	C3—C4—C5	124.1 (6)
O1^i—Co1—O1	180.0	C13—C11—C12	109.9 (7)
O2^i—Co1—N1	89.70 (18)	C13—C11—C5	112.8 (6)
O2—Co1—N1	90.30 (18)	C12—C11—C5	108.6 (6)
O1^i—Co1—N1	87.17 (17)	C13—C11—C14	106.2 (7)
O1—Co1—N1	92.83 (17)	C12—C11—C14	108.7 (7)
O2^i—Co1—N1^i	90.30 (18)	C5—C11—C14	110.7 (5)
O2—Co1—N1^i	89.70 (18)	C6—C5—C4	119.0 (5)
O1^i—Co1—N1^i	92.83 (17)	C6—C5—C11	122.3 (6)
O1—Co1—N1^i	87.17 (17)	C4—C5—C11	118.6 (6)
N1—Co1—N1^i	180.0	O1—C1—C6	123.0 (5)
C2—O2—Co1	111.8 (3)	O1—C1—C2	117.7 (5)
C1—O1—Co1	111.7 (3)	C6—C1—C2	119.3 (5)
C19—N1—C15	118.3 (6)	C5—C6—C1	120.7 (6)
C19—N1—Co1	120.8 (5)	C17—C18—C19	121.5 (7)
C15—N1—Co1	120.9 (5)	C17—C18—Cl1	120.7 (6)
O2—C2—C3	124.0 (5)	C19—C18—Cl1	117.8 (6)
O2—C2—C1	116.2 (5)	N1—C19—C18	121.6 (7)
C3—C2—C1	119.7 (5)	C17—C16—C15	120.6 (7)
C4—C3—C2	117.1 (5)	C17—C16—Cl2	120.3 (6)
C4—C3—C7	123.5 (5)	C15—C16—Cl2	119.1 (6)
C2—C3—C7	119.4 (5)	C18—C17—C16	116.5 (7)
C8—C7—C9	110.1 (6)	N1—C15—C16	121.6 (7)
C8—C7—C3	110.9 (5)
Co1—O2—C2—C3	−175.8 (5)	Co1—O1—C1—C6	174.7 (4)
Co1—O2—C2—C1	3.8 (6)	Co1—O1—C1—C2	−5.2 (6)
O2—C2—C3—C4	−178.9 (6)	O2—C2—C1—O1	0.9 (8)
C1—C2—C3—C4	1.4 (8)	C3—C2—C1—O1	−179.4 (5)
O2—C2—C3—C7	−0.7 (9)	O2—C2—C1—C6	−179.0 (5)
C1—C2—C3—C7	179.6 (5)	C3—C2—C1—C6	0.7 (8)
C4—C3—C7—C8	−122.9 (6)	C4—C5—C6—C1	2.7 (9)
C2—C3—C7—C8	59.0 (7)	C11—C5—C6—C1	−175.9 (5)
C4—C3—C7—C9	115.1 (7)	O1—C1—C6—C5	177.3 (6)
C2—C3—C7—C9	−63.0 (7)	C2—C1—C6—C5	−2.8 (8)
C4—C3—C7—C10	−2.7 (9)	C15—N1—C19—C18	0.0 (9)
C2—C3—C7—C10	179.2 (6)	Co1—N1—C19—C18	−178.4 (5)
C2—C3—C4—C5	−1.6 (9)	C17—C18—C19—N1	0.6 (11)
C7—C3—C4—C5	−179.7 (6)	Cl1—C18—C19—N1	−179.8 (5)
C3—C4—C5—C6	−0.4 (10)	C19—C18—C17—C16	−0.3 (11)
C3—C4—C5—C11	178.2 (6)	Cl1—C18—C17—C16	−179.8 (5)
C13—C11—C5—C6	−10.3 (10)	C15—C16—C17—C18	−0.7 (11)
C12—C11—C5—C6	111.6 (8)	Cl2—C16—C17—C18	178.8 (6)
C14—C11—C5—C6	−129.1 (7)	C19—N1—C15—C16	−1.0 (9)
C13—C11—C5—C4	171.1 (7)	Co1—N1—C15—C16	177.4 (5)
C12—C11—C5—C4	−66.9 (8)	C17—C16—C15—N1	1.4 (11)
C14—C11—C5—C4	52.3 (8)	Cl2—C16—C15—N1	−178.1 (5)

Symmetry code: (i) −x+1, −y, −z+2.

(2S_296K)

Crystal data

C38H46Cl4CoN2O4	Dx = 1.191 Mg m^−3
Mr = 795.50	Ag Kα radiation, λ = 0.56085 Å
Trigonal, P3	Cell parameters from 11261 reflections
a = 20.643 (18) Å	θ = 0.9–21.1°
c = 9.015 (7) Å	µ = 0.35 mm^−1
V = 3327 (6) Å^3	T = 296 K
Z = 3	Block, blue
F(000) = 1245	0.18 × 0.16 × 0.10 mm

Data collection

Bruker Kappa APEX II CCD detector diffractometer	4870 independent reflections
Radiation source: Bruker, Kappa Apex II	1440 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.154
φ and ω scans	θmax = 21.1°, θmin = 0.9°
Absorption correction: multi-scan Bruker AXS, 2008	h = −23→21
Tmin = 0.940, Tmax = 0.966	k = −26→18
11261 measured reflections	l = −9→11

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.120	w = 1/[σ^2(Fo^2) + (0.1446P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.350	(Δ/σ)max < 0.001
S = 0.87	Δρmax = 0.65 e Å^−3
4870 reflections	Δρmin = −0.45 e Å^−3
230 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.029 (5)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.3454 (4)	0.9333 (4)	0.4892 (9)	0.0420 (19)
C2	0.3693 (5)	0.9539 (5)	0.3312 (9)	0.050 (2)
C3	0.3143 (5)	0.9321 (5)	0.2146 (10)	0.059 (2)
C4	0.2433 (5)	0.8971 (5)	0.2536 (10)	0.061 (2)
H4	0.2078	0.8856	0.1795	0.073*
C5	0.2163 (5)	0.8751 (5)	0.4069 (10)	0.056 (2)
C6	0.2666 (5)	0.8927 (4)	0.5189 (9)	0.052 (2)
H6	0.2497	0.8782	0.6155	0.062*
C7	0.3424 (5)	0.9540 (6)	0.0516 (10)	0.072 (3)
C8	0.3880 (6)	0.9185 (6)	0.0046 (11)	0.076 (3)
H8A	0.4341	0.9407	0.0589	0.113*
H8B	0.3984	0.9264	−0.0997	0.113*
H8C	0.3602	0.8658	0.0246	0.113*
C9	0.3886 (7)	1.0393 (6)	0.0357 (13)	0.099 (4)
H9A	0.3634	1.0616	0.0852	0.149*
H9B	0.3942	1.0524	−0.0675	0.149*
H9C	0.4370	1.0572	0.0794	0.149*
C10	0.2737 (6)	0.9271 (7)	−0.0570 (11)	0.103 (4)
H10A	0.2451	0.9502	−0.0296	0.155*
H10B	0.2427	0.8737	−0.0506	0.155*
H10C	0.2915	0.9408	−0.1568	0.155*
C11	0.1299 (5)	0.8365 (5)	0.4385 (11)	0.067 (3)
C12	0.0891 (6)	0.7697 (7)	0.3310 (17)	0.115 (5)
H12A	0.1121	0.7835	0.2350	0.173*
H12B	0.0375	0.7563	0.3233	0.173*
H12C	0.0924	0.7278	0.3680	0.173*
C13	0.1123 (7)	0.8094 (9)	0.5950 (16)	0.144 (7)
H13A	0.1393	0.7843	0.6208	0.216*
H13B	0.0596	0.7752	0.6045	0.216*
H13C	0.1267	0.8512	0.6602	0.216*
C14	0.1032 (6)	0.8918 (7)	0.4113 (17)	0.113 (5)
H14A	0.1083	0.9192	0.5007	0.170*
H14B	0.0517	0.8653	0.3816	0.170*
H14C	0.1328	0.9259	0.3342	0.170*
C15	0.4759 (5)	0.8567 (6)	0.3368 (11)	0.066 (3)
H15	0.4781	0.8840	0.2530	0.079*
C16	0.4667 (6)	0.7863 (7)	0.3228 (15)	0.093 (4)
C17	0.4628 (6)	0.7434 (6)	0.4336 (17)	0.090 (4)
H17	0.4585	0.6968	0.4193	0.108*
C18	0.4659 (6)	0.7737 (6)	0.5793 (13)	0.079 (3)
C19	0.4755 (5)	0.8448 (5)	0.5956 (13)	0.072 (3)
H19	0.4779	0.8644	0.6897	0.087*
Cl1	0.4631 (2)	0.7242 (2)	0.7325 (5)	0.1330 (15)
Cl2	0.4607 (3)	0.7535 (2)	0.1379 (5)	0.1427 (16)
Co1	0.5000	1.0000	0.5000	0.0493 (6)
N1	0.4816 (4)	0.8856 (4)	0.4724 (9)	0.061 (2)
O1	0.3950 (3)	0.9523 (3)	0.5866 (6)	0.0562 (15)
O2	0.4413 (3)	0.9876 (3)	0.3102 (6)	0.0522 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.038 (5)	0.038 (4)	0.045 (5)	0.014 (4)	−0.003 (4)	−0.002 (3)
C2	0.047 (5)	0.049 (5)	0.044 (5)	0.016 (4)	−0.006 (4)	0.001 (4)
C3	0.047 (5)	0.043 (5)	0.070 (7)	0.008 (4)	−0.006 (4)	−0.009 (4)
C4	0.063 (6)	0.059 (6)	0.046 (5)	0.019 (5)	−0.012 (4)	−0.007 (4)
C5	0.044 (5)	0.055 (5)	0.064 (6)	0.021 (4)	0.008 (4)	−0.004 (4)
C6	0.059 (6)	0.048 (5)	0.045 (5)	0.025 (4)	−0.004 (4)	−0.002 (4)
C7	0.061 (6)	0.086 (7)	0.041 (5)	0.016 (6)	−0.012 (4)	0.001 (5)
C8	0.087 (7)	0.095 (8)	0.045 (6)	0.046 (6)	0.008 (5)	0.002 (5)
C9	0.120 (10)	0.090 (8)	0.071 (8)	0.040 (8)	−0.021 (7)	0.024 (6)
C10	0.094 (8)	0.142 (11)	0.047 (7)	0.039 (8)	−0.009 (6)	0.015 (6)
C11	0.041 (5)	0.071 (6)	0.073 (7)	0.017 (5)	0.003 (5)	−0.012 (5)
C12	0.049 (7)	0.094 (9)	0.176 (15)	0.015 (6)	−0.001 (7)	−0.029 (9)
C13	0.072 (8)	0.217 (17)	0.128 (13)	0.062 (10)	0.065 (8)	0.067 (12)
C14	0.061 (7)	0.100 (9)	0.184 (15)	0.044 (7)	0.022 (8)	0.026 (9)
C15	0.070 (6)	0.075 (7)	0.057 (6)	0.039 (5)	−0.007 (5)	−0.010 (5)
C16	0.079 (8)	0.080 (8)	0.119 (11)	0.039 (7)	−0.002 (7)	−0.049 (8)
C17	0.064 (7)	0.051 (7)	0.147 (13)	0.022 (6)	−0.002 (7)	0.012 (8)
C18	0.072 (7)	0.069 (7)	0.089 (9)	0.030 (6)	0.001 (6)	0.010 (6)
C19	0.054 (6)	0.051 (6)	0.107 (9)	0.023 (5)	−0.011 (5)	0.005 (6)
Cl1	0.166 (4)	0.102 (3)	0.135 (3)	0.069 (3)	−0.001 (3)	0.037 (2)
Cl2	0.181 (4)	0.147 (3)	0.121 (3)	0.098 (3)	−0.016 (3)	−0.065 (3)
Co1	0.0441 (10)	0.0499 (11)	0.0459 (10)	0.0174 (8)	−0.0054 (7)	−0.0037 (7)
N1	0.040 (4)	0.061 (5)	0.080 (6)	0.024 (4)	−0.004 (4)	0.001 (4)
O1	0.053 (4)	0.068 (4)	0.040 (3)	0.025 (3)	−0.009 (3)	−0.005 (3)
O2	0.044 (4)	0.055 (3)	0.047 (3)	0.017 (3)	0.000 (3)	−0.001 (3)

Geometric parameters (Å, º)

C1—O1	1.253 (9)	C12—H12A	0.9600
C1—C6	1.433 (11)	C12—H12B	0.9600
C1—C2	1.499 (11)	C12—H12C	0.9600
C2—O2	1.302 (9)	C13—H13A	0.9600
C2—C3	1.444 (12)	C13—H13B	0.9600
C3—C4	1.318 (12)	C13—H13C	0.9600
C3—C7	1.561 (13)	C14—H14A	0.9600
C4—C5	1.474 (12)	C14—H14B	0.9600
C4—H4	0.9300	C14—H14C	0.9600
C5—C6	1.361 (11)	C15—N1	1.339 (11)
C5—C11	1.574 (12)	C15—C16	1.373 (15)
C6—H6	0.9300	C15—H15	0.9300
C7—C8	1.514 (14)	C16—C17	1.311 (17)
C7—C9	1.533 (14)	C16—Cl2	1.781 (12)
C7—C10	1.579 (13)	C17—C18	1.443 (16)
C8—H8A	0.9600	C17—H17	0.9300
C8—H8B	0.9600	C18—C19	1.386 (14)
C8—H8C	0.9600	C18—Cl1	1.702 (12)
C9—H9A	0.9600	C19—N1	1.362 (12)
C9—H9B	0.9600	C19—H19	0.9300
C9—H9C	0.9600	Co1—O1^i	2.036 (6)
C10—H10A	0.9600	Co1—O1	2.036 (6)
C10—H10B	0.9600	Co1—O2^i	2.037 (5)
C10—H10C	0.9600	Co1—O2	2.037 (5)
C11—C13	1.494 (15)	Co1—N1^i	2.210 (8)
C11—C14	1.515 (15)	Co1—N1	2.210 (8)
C11—C12	1.545 (14)
O1—C1—C6	124.2 (7)	C11—C12—H12C	109.5
O1—C1—C2	118.4 (7)	H12A—C12—H12C	109.5
C6—C1—C2	117.4 (7)	H12B—C12—H12C	109.5
O2—C2—C3	124.8 (7)	C11—C13—H13A	109.5
O2—C2—C1	114.6 (6)	C11—C13—H13B	109.5
C3—C2—C1	120.5 (7)	H13A—C13—H13B	109.5
C4—C3—C2	117.6 (9)	C11—C13—H13C	109.5
C4—C3—C7	124.1 (8)	H13A—C13—H13C	109.5
C2—C3—C7	118.3 (7)	H13B—C13—H13C	109.5
C3—C4—C5	124.4 (9)	C11—C14—H14A	109.5
C3—C4—H4	117.8	C11—C14—H14B	109.5
C5—C4—H4	117.8	H14A—C14—H14B	109.5
C6—C5—C4	119.5 (8)	C11—C14—H14C	109.5
C6—C5—C11	121.4 (8)	H14A—C14—H14C	109.5
C4—C5—C11	118.9 (8)	H14B—C14—H14C	109.5
C5—C6—C1	120.6 (8)	N1—C15—C16	119.4 (10)
C5—C6—H6	119.7	N1—C15—H15	120.3
C1—C6—H6	119.7	C16—C15—H15	120.3
C8—C7—C9	110.5 (9)	C17—C16—C15	125.1 (12)
C8—C7—C3	110.7 (8)	C17—C16—Cl2	119.1 (10)
C9—C7—C3	110.4 (8)	C15—C16—Cl2	115.8 (11)
C8—C7—C10	108.8 (9)	C16—C17—C18	115.1 (11)
C9—C7—C10	106.2 (9)	C16—C17—H17	122.4
C3—C7—C10	110.1 (8)	C18—C17—H17	122.4
C7—C8—H8A	109.5	C19—C18—C17	120.5 (11)
C7—C8—H8B	109.5	C19—C18—Cl1	119.6 (10)
H8A—C8—H8B	109.5	C17—C18—Cl1	119.7 (9)
C7—C8—H8C	109.5	N1—C19—C18	119.2 (11)
H8A—C8—H8C	109.5	N1—C19—H19	120.4
H8B—C8—H8C	109.5	C18—C19—H19	120.4
C7—C9—H9A	109.5	O1^i—Co1—O1	180.0
C7—C9—H9B	109.5	O1^i—Co1—O2^i	80.7 (2)
H9A—C9—H9B	109.5	O1—Co1—O2^i	99.3 (2)
C7—C9—H9C	109.5	O1^i—Co1—O2	99.3 (2)
H9A—C9—H9C	109.5	O1—Co1—O2	80.7 (2)
H9B—C9—H9C	109.5	O2^i—Co1—O2	180.0
C7—C10—H10A	109.5	O1^i—Co1—N1^i	87.3 (2)
C7—C10—H10B	109.5	O1—Co1—N1^i	92.7 (2)
H10A—C10—H10B	109.5	O2^i—Co1—N1^i	89.8 (3)
C7—C10—H10C	109.5	O2—Co1—N1^i	90.2 (3)
H10A—C10—H10C	109.5	O1^i—Co1—N1	92.7 (2)
H10B—C10—H10C	109.5	O1—Co1—N1	87.3 (2)
C13—C11—C14	108.9 (10)	O2^i—Co1—N1	90.2 (3)
C13—C11—C12	109.6 (11)	O2—Co1—N1	89.8 (3)
C14—C11—C12	109.2 (10)	N1^i—Co1—N1	180.0
C13—C11—C5	111.2 (8)	C15—N1—C19	120.6 (9)
C14—C11—C5	109.6 (8)	C15—N1—Co1	120.6 (7)
C12—C11—C5	108.2 (8)	C19—N1—Co1	118.8 (7)
C11—C12—H12A	109.5	C1—O1—Co1	112.9 (5)
C11—C12—H12B	109.5	C2—O2—Co1	113.2 (5)
H12A—C12—H12B	109.5

Symmetry code: (i) −x+1, −y+2, −z+1.

(3_100K)

Crystal data

C38H44Br6CoN2O4	Z = 1
Mr = 1131.14	F(000) = 555
Triclinic, P1	Dx = 1.733 Mg m^−3
a = 8.8113 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.7232 (5) Å	Cell parameters from 22375 reflections
c = 11.5220 (5) Å	θ = 1.8–26.0°
α = 91.925 (4)°	µ = 5.97 mm^−1
β = 93.441 (3)°	T = 100 K
γ = 93.722 (3)°	Block, blue
V = 1083.64 (8) Å^3	0.21 × 0.18 × 0.10 mm

Data collection

SuperNova, Single source at offset), Atlas diffractometer	4158 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2945 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.074
ω scans	θmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.35 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −10→10
Tmin = 0.367, Tmax = 0.587	k = −13→13
22375 measured reflections	l = −14→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.085	w = 1/[σ^2(Fo^2) + (0.0263P)^2 + 1.688P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
4158 reflections	Δρmax = 0.77 e Å^−3
238 parameters	Δρmin = −0.61 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.4495 (5)	0.9017 (4)	0.7720 (4)	0.0131 (10)
C2	0.2979 (5)	0.8963 (4)	0.8183 (4)	0.0148 (10)
C3	0.1681 (5)	0.8471 (4)	0.7461 (4)	0.0151 (10)
C4	0.1944 (5)	0.8070 (4)	0.6348 (4)	0.0203 (11)
H4	0.1092	0.7746	0.5860	0.024*
C5	0.3415 (6)	0.8107 (4)	0.5870 (4)	0.0198 (11)
C6	0.4645 (5)	0.8576 (4)	0.6564 (4)	0.0163 (10)
H6	0.5627	0.8607	0.6264	0.020*
C7	0.0078 (5)	0.8407 (4)	0.7933 (4)	0.0209 (11)
C8	−0.0354 (5)	0.9735 (4)	0.8239 (5)	0.0241 (12)
H8A	0.0292	1.0078	0.8911	0.036*
H8B	−0.1425	0.9711	0.8428	0.036*
H8C	−0.0206	1.0266	0.7573	0.036*
C9	0.0063 (5)	0.7621 (5)	0.9015 (4)	0.0235 (12)
H9A	0.0754	0.8030	0.9632	0.035*
H9B	0.0398	0.6789	0.8826	0.035*
H9C	−0.0973	0.7540	0.9282	0.035*
C10	−0.1127 (5)	0.7820 (5)	0.7037 (5)	0.0300 (13)
H10A	−0.2121	0.7769	0.7377	0.045*
H10B	−0.0858	0.6978	0.6807	0.045*
H10C	−0.1176	0.8336	0.6351	0.045*
C11	0.3525 (6)	0.7621 (5)	0.4636 (4)	0.0270 (12)
C12	0.2510 (6)	0.8340 (5)	0.3797 (5)	0.0312 (13)
H12A	0.1462	0.8282	0.4040	0.047*
H12B	0.2531	0.7976	0.3007	0.047*
H12C	0.2891	0.9219	0.3809	0.047*
C13	0.5154 (6)	0.7781 (6)	0.4238 (5)	0.0427 (16)
H13A	0.5526	0.8662	0.4337	0.064*
H13B	0.5160	0.7515	0.3417	0.064*
H13C	0.5818	0.7268	0.4707	0.064*
C14	0.2992 (8)	0.6218 (5)	0.4530 (5)	0.0437 (16)
H14A	0.3647	0.5748	0.5048	0.065*
H14B	0.3054	0.5911	0.3725	0.065*
H14C	0.1936	0.6106	0.4750	0.065*
C15	0.3306 (5)	1.2179 (4)	0.8907 (4)	0.0155 (10)
H15	0.2457	1.1587	0.8914	0.019*
C16	0.3088 (5)	1.3344 (4)	0.8453 (4)	0.0174 (11)
C17	0.4319 (5)	1.4217 (4)	0.8429 (4)	0.0157 (10)
C18	0.5720 (5)	1.3869 (4)	0.8867 (4)	0.0173 (11)
C19	0.5855 (5)	1.2686 (4)	0.9309 (4)	0.0157 (10)
H19	0.6827	1.2461	0.9601	0.019*
N1	0.4665 (4)	1.1863 (3)	0.9335 (3)	0.0148 (9)
O1	0.5633 (3)	0.9449 (3)	0.8397 (3)	0.0167 (7)
O2	0.2908 (3)	0.9373 (3)	0.9248 (3)	0.0168 (7)
Co1	0.5000	1.0000	1.0000	0.0139 (2)
Br1	0.75073 (6)	1.49482 (4)	0.88930 (5)	0.02575 (15)
Br2	0.41122 (7)	1.57889 (4)	0.77945 (5)	0.03014 (16)
Br3	0.11159 (6)	1.36582 (5)	0.78769 (5)	0.03332 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.012 (3)	0.010 (2)	0.018 (3)	0.0029 (19)	0.001 (2)	0.0030 (19)
C2	0.018 (3)	0.008 (2)	0.019 (3)	0.0030 (19)	0.000 (2)	0.0044 (19)
C3	0.014 (3)	0.013 (2)	0.019 (3)	0.0027 (19)	−0.001 (2)	0.003 (2)
C4	0.020 (3)	0.020 (2)	0.021 (3)	0.001 (2)	−0.002 (2)	0.005 (2)
C5	0.025 (3)	0.018 (2)	0.018 (3)	0.008 (2)	0.005 (2)	0.003 (2)
C6	0.014 (3)	0.017 (2)	0.018 (3)	0.003 (2)	−0.001 (2)	0.001 (2)
C7	0.020 (3)	0.023 (3)	0.020 (3)	0.002 (2)	0.001 (2)	0.001 (2)
C8	0.013 (3)	0.027 (3)	0.033 (3)	0.007 (2)	0.001 (2)	0.000 (2)
C9	0.016 (3)	0.026 (3)	0.028 (3)	−0.009 (2)	0.004 (2)	0.003 (2)
C10	0.013 (3)	0.035 (3)	0.041 (4)	−0.003 (2)	−0.003 (2)	0.003 (3)
C11	0.029 (3)	0.032 (3)	0.019 (3)	0.004 (2)	−0.001 (2)	−0.003 (2)
C12	0.035 (3)	0.037 (3)	0.021 (3)	0.001 (3)	−0.006 (3)	0.000 (2)
C13	0.035 (4)	0.071 (5)	0.022 (3)	0.005 (3)	0.006 (3)	−0.013 (3)
C14	0.073 (5)	0.033 (3)	0.024 (3)	0.011 (3)	−0.002 (3)	−0.008 (3)
C15	0.015 (3)	0.014 (2)	0.016 (3)	−0.002 (2)	0.003 (2)	0.0000 (19)
C16	0.017 (3)	0.017 (2)	0.019 (3)	0.008 (2)	0.002 (2)	−0.002 (2)
C17	0.025 (3)	0.011 (2)	0.011 (2)	0.003 (2)	0.002 (2)	−0.0012 (18)
C18	0.024 (3)	0.016 (2)	0.011 (3)	−0.002 (2)	0.005 (2)	−0.002 (2)
C19	0.015 (3)	0.020 (2)	0.013 (3)	0.004 (2)	0.000 (2)	0.001 (2)
N1	0.012 (2)	0.0151 (19)	0.018 (2)	0.0026 (17)	0.0033 (17)	0.0022 (16)
O1	0.0150 (18)	0.0195 (17)	0.0156 (18)	0.0025 (14)	−0.0014 (14)	0.0015 (14)
O2	0.0173 (18)	0.0169 (17)	0.0160 (19)	0.0015 (14)	−0.0005 (14)	0.0005 (14)
Co1	0.0145 (5)	0.0126 (4)	0.0143 (5)	0.0000 (4)	−0.0009 (4)	0.0006 (4)
Br1	0.0283 (3)	0.0202 (3)	0.0279 (3)	−0.0081 (2)	0.0053 (2)	0.0006 (2)
Br2	0.0465 (4)	0.0151 (3)	0.0295 (3)	0.0067 (2)	−0.0001 (3)	0.0067 (2)
Br3	0.0247 (3)	0.0297 (3)	0.0456 (4)	0.0104 (2)	−0.0080 (3)	0.0052 (3)

Geometric parameters (Å, º)

C1—O1	1.284 (5)	C15—N1	1.336 (5)
C1—C6	1.415 (6)	C15—C16	1.391 (6)
C1—C2	1.465 (6)	C16—C17	1.388 (6)
C2—O2	1.297 (5)	C16—Br3	1.878 (5)
C2—C3	1.434 (6)	C17—C18	1.384 (6)
C3—C4	1.377 (7)	C17—Br2	1.875 (4)
C3—C7	1.541 (7)	C18—C19	1.392 (6)
C4—C5	1.436 (7)	C18—Br1	1.891 (5)
C5—C6	1.366 (7)	C19—N1	1.328 (6)
C5—C11	1.509 (7)	N1—Co1	2.194 (3)
C7—C10	1.525 (7)	O1—Co1	2.040 (3)
C7—C9	1.529 (6)	O2—Co1	2.051 (3)
C7—C8	1.534 (6)	Co1—O1^i	2.040 (3)
C11—C13	1.534 (7)	Co1—O2^i	2.051 (3)
C11—C12	1.537 (7)	Co1—N1^i	2.194 (4)
C11—C14	1.545 (7)
O1—C1—C6	123.0 (4)	C15—C16—Br3	117.8 (4)
O1—C1—C2	118.0 (4)	C18—C17—C16	117.2 (4)
C6—C1—C2	119.0 (4)	C18—C17—Br2	121.1 (4)
O2—C2—C3	123.8 (4)	C16—C17—Br2	121.6 (3)
O2—C2—C1	116.4 (4)	C17—C18—C19	120.2 (4)
C3—C2—C1	119.8 (4)	C17—C18—Br1	122.4 (3)
C4—C3—C2	116.9 (4)	C19—C18—Br1	117.4 (4)
C4—C3—C7	122.7 (4)	N1—C19—C18	122.0 (4)
C2—C3—C7	120.5 (4)	C19—N1—C15	118.7 (4)
C3—C4—C5	124.7 (5)	C19—N1—Co1	119.4 (3)
C6—C5—C4	118.0 (4)	C15—N1—Co1	121.9 (3)
C6—C5—C11	123.4 (4)	C1—O1—Co1	112.5 (3)
C4—C5—C11	118.6 (4)	C2—O2—Co1	112.6 (3)
C5—C6—C1	121.7 (4)	O1—Co1—O1^i	180.0 (2)
C10—C7—C9	108.1 (4)	O1—Co1—O2	80.53 (12)
C10—C7—C8	107.9 (4)	O1^i—Co1—O2	99.47 (12)
C9—C7—C8	109.8 (4)	O1—Co1—O2^i	99.47 (12)
C10—C7—C3	111.9 (4)	O1^i—Co1—O2^i	80.53 (12)
C9—C7—C3	109.9 (4)	O2—Co1—O2^i	180.00 (16)
C8—C7—C3	109.2 (4)	O1—Co1—N1	88.89 (13)
C5—C11—C13	112.2 (4)	O1^i—Co1—N1	91.11 (13)
C5—C11—C12	110.2 (4)	O2—Co1—N1	89.59 (13)
C13—C11—C12	107.1 (4)	O2^i—Co1—N1	90.41 (13)
C5—C11—C14	109.9 (4)	O1—Co1—N1^i	91.11 (13)
C13—C11—C14	108.6 (5)	O1^i—Co1—N1^i	88.89 (13)
C12—C11—C14	108.8 (4)	O2—Co1—N1^i	90.41 (13)
N1—C15—C16	122.4 (4)	O2^i—Co1—N1^i	89.59 (13)
C17—C16—C15	119.5 (4)	N1—Co1—N1^i	180.0
C17—C16—Br3	122.7 (3)
O1—C1—C2—O2	0.7 (6)	C6—C5—C11—C12	−122.4 (5)
C6—C1—C2—O2	179.7 (4)	C4—C5—C11—C12	58.1 (6)
O1—C1—C2—C3	−179.1 (4)	C6—C5—C11—C14	117.8 (5)
C6—C1—C2—C3	−0.2 (6)	C4—C5—C11—C14	−61.7 (6)
O2—C2—C3—C4	−179.9 (4)	N1—C15—C16—C17	0.5 (7)
C1—C2—C3—C4	−0.1 (6)	N1—C15—C16—Br3	179.8 (3)
O2—C2—C3—C7	0.1 (6)	C15—C16—C17—C18	0.1 (7)
C1—C2—C3—C7	180.0 (4)	Br3—C16—C17—C18	−179.2 (3)
C2—C3—C4—C5	0.3 (7)	C15—C16—C17—Br2	178.5 (3)
C7—C3—C4—C5	−179.8 (4)	Br3—C16—C17—Br2	−0.8 (6)
C3—C4—C5—C6	−0.2 (7)	C16—C17—C18—C19	−0.1 (7)
C3—C4—C5—C11	179.4 (4)	Br2—C17—C18—C19	−178.5 (3)
C4—C5—C6—C1	−0.1 (7)	C16—C17—C18—Br1	179.8 (3)
C11—C5—C6—C1	−179.6 (4)	Br2—C17—C18—Br1	1.4 (6)
O1—C1—C6—C5	179.2 (4)	C17—C18—C19—N1	−0.4 (7)
C2—C1—C6—C5	0.3 (6)	Br1—C18—C19—N1	179.6 (3)
C4—C3—C7—C10	1.7 (6)	C18—C19—N1—C15	1.0 (7)
C2—C3—C7—C10	−178.3 (4)	C18—C19—N1—Co1	178.2 (3)
C4—C3—C7—C9	121.9 (5)	C16—C15—N1—C19	−1.0 (7)
C2—C3—C7—C9	−58.2 (5)	C16—C15—N1—Co1	−178.1 (3)
C4—C3—C7—C8	−117.6 (5)	C6—C1—O1—Co1	180.0 (3)
C2—C3—C7—C8	62.3 (5)	C2—C1—O1—Co1	−1.1 (5)
C6—C5—C11—C13	−3.1 (7)	C3—C2—O2—Co1	179.9 (3)
C4—C5—C11—C13	177.4 (4)	C1—C2—O2—Co1	0.0 (4)

Symmetry code: (i) −x+1, −y+2, −z+2.

(3_20K)

Crystal data

C38H44Br6CoN2O4	Z = 1
Mr = 1131.08	F(000) = 555
Triclinic, P1	Dx = 1.748 Mg m^−3
a = 8.8070 (6) Å	Synchrotron,monochromatic radiation, λ = 0.4997 Å
b = 10.6922 (8) Å	Cell parameters from 10578 reflections
c = 11.4658 (13) Å	θ = 1.3–17.4°
α = 91.692 (8)°	µ = 2.37 mm^−1
β = 93.393 (7)°	T = 20 K
γ = 93.903 (6)°	Block, blue
V = 1074.69 (16) Å^3	0.11 × 0.09 × 0.09 mm

Data collection

Rigaku kappa diffractometer	3504 reflections with I > 2σ(I)
Radiation source: SPring-8,BL02B1	Rint = 0.066
Absorption correction: empirical (using intensity measurements) Blessing, 1995	θmax = 18.2°, θmin = 1.3°
Tmin = 0.781, Tmax = 0.815	h = −10→11
10578 measured reflections	k = −13→13
4320 independent reflections	l = −14→13

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.060	w = 1/[σ^2(Fo^2) + (0.1006P)^2 + 1.3323P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.152	(Δ/σ)max < 0.001
S = 1.12	Δρmax = 1.81 e Å^−3
4320 reflections	Δρmin = −2.09 e Å^−3
232 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.020 (3)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.0497 (6)	0.0975 (5)	0.7284 (5)	0.0183 (9)
C2	0.2027 (6)	0.1026 (5)	0.6806 (5)	0.0183 (9)
C3	0.3305 (7)	0.1513 (5)	0.7548 (6)	0.0210 (13)
C4	0.3051 (7)	0.1914 (5)	0.8652 (6)	0.0209 (13)
H4	0.3908	0.2243	0.9135	0.025*
C5	0.1582 (7)	0.1879 (6)	0.9145 (5)	0.0211 (13)
C6	0.0349 (7)	0.1414 (6)	0.8442 (5)	0.0207 (13)
H6	−0.0635	0.1387	0.8742	0.025*
C7	0.4908 (7)	0.1576 (6)	0.7067 (5)	0.0203 (13)
C8	0.5342 (7)	0.0247 (6)	0.6748 (6)	0.0239 (14)
H8A	0.6380	0.0288	0.6480	0.036*
H8B	0.4629	−0.0122	0.6122	0.036*
H8C	0.5294	−0.0272	0.7436	0.036*
C9	0.4929 (7)	0.2382 (6)	0.5975 (5)	0.0223 (14)
H9A	0.4558	0.3203	0.6162	0.033*
H9B	0.4268	0.1962	0.5344	0.033*
H9C	0.5973	0.2493	0.5726	0.033*
C10	0.6132 (7)	0.2166 (6)	0.7974 (6)	0.0242 (14)
H10A	0.5859	0.3005	0.8215	0.036*
H10B	0.7123	0.2231	0.7626	0.036*
H10C	0.6191	0.1639	0.8658	0.036*
C11	0.1462 (7)	0.2381 (6)	1.0386 (6)	0.0253 (15)
C12	0.2503 (7)	0.1665 (6)	1.1229 (6)	0.0271 (15)
H12A	0.3554	0.1757	1.0991	0.041*
H12B	0.2152	0.0774	1.1201	0.041*
H12C	0.2461	0.2009	1.2027	0.041*
C13	−0.0164 (8)	0.2202 (7)	1.0776 (6)	0.0324 (16)
H13A	−0.0183	0.2478	1.1597	0.049*
H13B	−0.0517	0.1313	1.0688	0.049*
H13C	−0.0834	0.2699	1.0292	0.049*
C14	0.1977 (8)	0.3784 (6)	1.0458 (6)	0.0291 (15)
H14A	0.1892	0.4113	1.1256	0.044*
H14B	0.1329	0.4234	0.9914	0.044*
H14C	0.3040	0.3898	1.0249	0.044*
C15	0.0877 (7)	0.2684 (6)	0.4313 (5)	0.0216 (14)
H15	0.1848	0.2463	0.4614	0.026*
C16	0.0752 (7)	0.3861 (6)	0.3872 (5)	0.0204 (13)
C17	−0.0657 (7)	0.4229 (5)	0.3443 (5)	0.0203 (13)
C18	−0.1917 (7)	0.3339 (6)	0.3458 (6)	0.0240 (14)
C19	−0.1680 (7)	0.2185 (6)	0.3927 (6)	0.0239 (14)
H19	−0.2538	0.1602	0.3964	0.029*
Br1	−0.38717 (7)	0.36768 (6)	0.29043 (6)	0.0264 (2)
Br2	−0.08605 (7)	0.58057 (6)	0.28109 (6)	0.02451 (19)
Br3	0.25350 (7)	0.49433 (5)	0.38920 (5)	0.02260 (19)
Co1	0.0000	0.0000	0.5000	0.0166 (3)
N1	−0.0322 (6)	0.1836 (5)	0.4333 (4)	0.0214 (11)
O1	−0.0635 (4)	0.0551 (4)	0.6599 (4)	0.0198 (9)
O2	0.2075 (4)	0.0616 (4)	0.5748 (4)	0.0192 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.019 (2)	0.007 (2)	0.028 (2)	−0.0035 (16)	0.0018 (18)	0.0083 (17)
C2	0.019 (2)	0.007 (2)	0.028 (2)	−0.0035 (16)	0.0018 (18)	0.0083 (17)
C3	0.028 (3)	0.006 (3)	0.028 (3)	−0.004 (2)	0.002 (3)	0.005 (2)
C4	0.023 (3)	0.010 (3)	0.029 (3)	−0.004 (2)	−0.006 (3)	0.008 (2)
C5	0.021 (3)	0.015 (3)	0.026 (3)	−0.004 (2)	0.000 (3)	0.009 (3)
C6	0.020 (3)	0.014 (3)	0.027 (3)	−0.002 (2)	0.001 (2)	0.004 (3)
C7	0.022 (3)	0.012 (3)	0.027 (3)	−0.004 (2)	0.004 (3)	0.005 (2)
C8	0.019 (3)	0.021 (3)	0.031 (4)	−0.006 (3)	0.001 (3)	0.006 (3)
C9	0.024 (3)	0.020 (3)	0.020 (3)	−0.012 (3)	0.001 (2)	0.005 (3)
C10	0.019 (3)	0.017 (3)	0.035 (4)	−0.005 (2)	0.000 (3)	0.000 (3)
C11	0.027 (3)	0.019 (3)	0.030 (4)	−0.005 (3)	0.006 (3)	0.005 (3)
C12	0.033 (4)	0.021 (3)	0.027 (4)	−0.004 (3)	−0.001 (3)	0.003 (3)
C13	0.036 (4)	0.029 (4)	0.032 (4)	0.000 (3)	0.003 (3)	0.004 (3)
C14	0.039 (4)	0.018 (4)	0.030 (4)	−0.004 (3)	0.002 (3)	−0.001 (3)
C15	0.021 (3)	0.021 (3)	0.021 (3)	−0.006 (3)	−0.001 (2)	0.005 (3)
C16	0.022 (3)	0.013 (3)	0.025 (3)	−0.007 (2)	−0.001 (2)	0.003 (2)
C17	0.031 (3)	0.007 (3)	0.023 (3)	−0.002 (2)	0.001 (3)	0.003 (2)
C18	0.032 (3)	0.015 (3)	0.024 (3)	−0.003 (3)	0.006 (3)	−0.001 (3)
C19	0.020 (3)	0.020 (3)	0.031 (4)	−0.012 (3)	0.006 (3)	0.003 (3)
Br1	0.0228 (3)	0.0169 (3)	0.0387 (4)	−0.0022 (2)	−0.0025 (3)	0.0040 (3)
Br2	0.0305 (4)	0.0118 (3)	0.0307 (4)	−0.0026 (2)	0.0002 (3)	0.0054 (2)
Br3	0.0238 (3)	0.0137 (3)	0.0290 (4)	−0.0089 (2)	0.0010 (2)	0.0040 (2)
Co1	0.0185 (6)	0.0080 (6)	0.0225 (6)	−0.0054 (4)	−0.0004 (5)	0.0030 (4)
N1	0.026 (3)	0.014 (3)	0.024 (3)	−0.002 (2)	0.000 (2)	0.002 (2)
O1	0.021 (2)	0.015 (2)	0.022 (2)	−0.0082 (17)	−0.0011 (17)	0.0039 (17)
O2	0.020 (2)	0.011 (2)	0.026 (2)	−0.0052 (16)	0.0022 (17)	0.0040 (17)

Geometric parameters (Å, º)

C1—O1	1.281 (7)	C12—H12A	0.9800
C1—C6	1.411 (9)	C12—H12B	0.9800
C1—C2	1.483 (8)	C12—H12C	0.9800
C2—O2	1.281 (8)	C13—H13A	0.9800
C2—C3	1.429 (8)	C13—H13B	0.9800
C3—C4	1.361 (9)	C13—H13C	0.9800
C3—C7	1.543 (8)	C14—H14A	0.9800
C4—C5	1.440 (9)	C14—H14B	0.9800
C4—H4	0.9500	C14—H14C	0.9800
C5—C6	1.369 (8)	C15—N1	1.346 (7)
C5—C11	1.519 (9)	C15—C16	1.379 (8)
C6—H6	0.9500	C15—H15	0.9500
C7—C8	1.536 (9)	C16—C17	1.393 (8)
C7—C9	1.541 (8)	C16—Br3	1.885 (6)
C7—C10	1.542 (8)	C17—C18	1.413 (8)
C8—H8A	0.9800	C17—Br2	1.870 (6)
C8—H8B	0.9800	C18—C19	1.385 (9)
C8—H8C	0.9800	C18—Br1	1.862 (7)
C9—H9A	0.9800	C19—N1	1.338 (8)
C9—H9B	0.9800	C19—H19	0.9500
C9—H9C	0.9800	Co1—O1^i	2.031 (4)
C10—H10A	0.9800	Co1—O1	2.031 (4)
C10—H10B	0.9800	Co1—O2^i	2.032 (4)
C10—H10C	0.9800	Co1—O2	2.032 (4)
C11—C13	1.526 (9)	Co1—N1	2.158 (5)
C11—C14	1.535 (9)	Co1—N1^i	2.158 (5)
C11—C12	1.547 (9)
O1—C1—C6	123.4 (5)	C11—C12—H12C	109.5
O1—C1—C2	117.2 (6)	H12A—C12—H12C	109.5
C6—C1—C2	119.4 (5)	H12B—C12—H12C	109.5
O2—C2—C3	125.8 (5)	C11—C13—H13A	109.5
O2—C2—C1	116.0 (5)	C11—C13—H13B	109.5
C3—C2—C1	118.2 (6)	H13A—C13—H13B	109.5
C4—C3—C2	118.3 (6)	C11—C13—H13C	109.5
C4—C3—C7	122.7 (5)	H13A—C13—H13C	109.5
C2—C3—C7	119.1 (6)	H13B—C13—H13C	109.5
C3—C4—C5	125.0 (6)	C11—C14—H14A	109.5
C3—C4—H4	117.5	C11—C14—H14B	109.5
C5—C4—H4	117.5	H14A—C14—H14B	109.5
C6—C5—C4	117.3 (6)	C11—C14—H14C	109.5
C6—C5—C11	123.3 (6)	H14A—C14—H14C	109.5
C4—C5—C11	119.4 (5)	H14B—C14—H14C	109.5
C5—C6—C1	121.9 (6)	N1—C15—C16	122.6 (6)
C5—C6—H6	119.0	N1—C15—H15	118.7
C1—C6—H6	119.0	C16—C15—H15	118.7
C8—C7—C9	109.6 (5)	C15—C16—C17	120.4 (5)
C8—C7—C10	107.9 (5)	C15—C16—Br3	117.7 (5)
C9—C7—C10	107.8 (5)	C17—C16—Br3	121.8 (4)
C8—C7—C3	109.8 (5)	C16—C17—C18	117.2 (5)
C9—C7—C3	110.0 (5)	C16—C17—Br2	121.5 (4)
C10—C7—C3	111.8 (5)	C18—C17—Br2	121.2 (5)
C7—C8—H8A	109.5	C19—C18—C17	118.1 (6)
C7—C8—H8B	109.5	C19—C18—Br1	119.3 (5)
H8A—C8—H8B	109.5	C17—C18—Br1	122.5 (5)
C7—C8—H8C	109.5	N1—C19—C18	124.4 (6)
H8A—C8—H8C	109.5	N1—C19—H19	117.8
H8B—C8—H8C	109.5	C18—C19—H19	117.8
C7—C9—H9A	109.5	O1^i—Co1—O1	180.0
C7—C9—H9B	109.5	O1^i—Co1—O2^i	80.66 (16)
H9A—C9—H9B	109.5	O1—Co1—O2^i	99.34 (16)
C7—C9—H9C	109.5	O1^i—Co1—O2	99.34 (16)
H9A—C9—H9C	109.5	O1—Co1—O2	80.66 (16)
H9B—C9—H9C	109.5	O2^i—Co1—O2	180.0
C7—C10—H10A	109.5	O1^i—Co1—N1	88.83 (18)
C7—C10—H10B	109.5	O1—Co1—N1	91.17 (18)
H10A—C10—H10B	109.5	O2^i—Co1—N1	89.33 (17)
C7—C10—H10C	109.5	O2—Co1—N1	90.67 (17)
H10A—C10—H10C	109.5	O1^i—Co1—N1^i	91.17 (18)
H10B—C10—H10C	109.5	O1—Co1—N1^i	88.83 (18)
C5—C11—C13	111.8 (5)	O2^i—Co1—N1^i	90.67 (17)
C5—C11—C14	109.2 (5)	O2—Co1—N1^i	89.33 (17)
C13—C11—C14	109.3 (6)	N1—Co1—N1^i	180.0
C5—C11—C12	109.2 (6)	C19—N1—C15	117.3 (5)
C13—C11—C12	107.8 (5)	C19—N1—Co1	122.9 (4)
C14—C11—C12	109.5 (5)	C15—N1—Co1	119.8 (4)
C11—C12—H12A	109.5	C1—O1—Co1	112.7 (4)
C11—C12—H12B	109.5	C2—O2—Co1	113.4 (4)
H12A—C12—H12B	109.5
O1—C1—C2—O2	−1.2 (8)	C6—C5—C11—C14	−116.3 (6)
C6—C1—C2—O2	−179.7 (5)	C4—C5—C11—C14	62.0 (7)
O1—C1—C2—C3	179.1 (5)	C6—C5—C11—C12	124.0 (6)
C6—C1—C2—C3	0.5 (8)	C4—C5—C11—C12	−57.8 (7)
O2—C2—C3—C4	179.8 (5)	N1—C15—C16—C17	1.3 (10)
C1—C2—C3—C4	−0.5 (8)	N1—C15—C16—Br3	−179.6 (5)
O2—C2—C3—C7	0.3 (9)	C15—C16—C17—C18	−1.6 (10)
C1—C2—C3—C7	−179.9 (5)	Br3—C16—C17—C18	179.4 (5)
C2—C3—C4—C5	0.5 (9)	C15—C16—C17—Br2	−178.7 (5)
C7—C3—C4—C5	180.0 (5)	Br3—C16—C17—Br2	2.2 (8)
C3—C4—C5—C6	−0.6 (9)	C16—C17—C18—C19	2.1 (9)
C3—C4—C5—C11	−178.9 (6)	Br2—C17—C18—C19	179.3 (5)
C4—C5—C6—C1	0.6 (9)	C16—C17—C18—Br1	−179.4 (5)
C11—C5—C6—C1	178.8 (6)	Br2—C17—C18—Br1	−2.2 (8)
O1—C1—C6—C5	−179.0 (5)	C17—C18—C19—N1	−2.5 (10)
C2—C1—C6—C5	−0.6 (9)	Br1—C18—C19—N1	178.9 (5)
C4—C3—C7—C8	118.3 (6)	C18—C19—N1—C15	2.2 (10)
C2—C3—C7—C8	−62.2 (7)	C18—C19—N1—Co1	−177.7 (5)
C4—C3—C7—C9	−121.0 (6)	C16—C15—N1—C19	−1.5 (10)
C2—C3—C7—C9	58.4 (7)	C16—C15—N1—Co1	178.4 (5)
C4—C3—C7—C10	−1.3 (8)	C6—C1—O1—Co1	−180.0 (4)
C2—C3—C7—C10	178.1 (5)	C2—C1—O1—Co1	1.6 (6)
C6—C5—C11—C13	4.8 (9)	C3—C2—O2—Co1	179.9 (4)
C4—C5—C11—C13	−177.0 (5)	C1—C2—O2—Co1	0.1 (6)

Symmetry code: (i) −x, −y, −z+1.

(3_296K)

Crystal data

C38H44Br6CoN2O4	Z = 1
Mr = 1131.08	F(000) = 555
Triclinic, P1	Dx = 1.687 Mg m^−3
a = 8.8725 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.7980 (3) Å	Cell parameters from 46994 reflections
c = 11.6965 (4) Å	θ = 1.7–27.0°
α = 92.641 (2)°	µ = 5.81 mm^−1
β = 94.358 (3)°	T = 296 K
γ = 93.791 (2)°	Block, blue
V = 1113.43 (6) Å^3	0.21 × 0.18 × 0.10 mm

Data collection

SuperNova, Single source at offset), Atlas diffractometer	4830 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2879 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.074
ω scans	θmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.35 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −11→11
Tmin = 0.375, Tmax = 0.594	k = −13→13
46994 measured reflections	l = −14→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.0403P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
4830 reflections	Δρmax = 0.40 e Å^−3
238 parameters	Δρmin = −0.35 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	−0.0510 (4)	−0.1018 (3)	0.2754 (3)	0.0386 (8)
C2	−0.2005 (4)	−0.1062 (3)	0.3182 (3)	0.0390 (8)
C3	−0.3308 (4)	−0.1563 (3)	0.2456 (3)	0.0476 (9)
C4	−0.3034 (5)	−0.1967 (3)	0.1369 (4)	0.0554 (10)
H4	−0.3862	−0.2284	0.0883	0.066*
C5	−0.1585 (5)	−0.1941 (4)	0.0926 (3)	0.0544 (10)
C6	−0.0357 (5)	−0.1463 (3)	0.1617 (3)	0.0525 (10)
H6	0.0596	−0.1430	0.1335	0.063*
C7	−0.4896 (4)	−0.1618 (4)	0.2897 (4)	0.0594 (11)
C8	−0.5322 (5)	−0.0291 (4)	0.3175 (4)	0.0775 (14)
H8A	−0.4643	0.0083	0.3792	0.116*
H8B	−0.6342	−0.0314	0.3399	0.116*
H8C	−0.5249	0.0189	0.2508	0.116*
C9	−0.4913 (5)	−0.2371 (4)	0.3969 (4)	0.0737 (13)
H9A	−0.4249	−0.1954	0.4573	0.111*
H9B	−0.4576	−0.3181	0.3800	0.111*
H9C	−0.5925	−0.2451	0.4208	0.111*
C10	−0.6082 (5)	−0.2235 (5)	0.1994 (5)	0.0944 (17)
H10A	−0.7053	−0.2292	0.2305	0.142*
H10B	−0.5804	−0.3054	0.1782	0.142*
H10C	−0.6134	−0.1747	0.1329	0.142*
C11	−0.1449 (6)	−0.2436 (5)	−0.0306 (4)	0.0791 (14)
C12	−0.2412 (7)	−0.1670 (6)	−0.1135 (4)	0.1082 (19)
H12A	−0.3448	−0.1735	−0.0947	0.162*
H12B	−0.2353	−0.1985	−0.1910	0.162*
H12C	−0.2032	−0.0814	−0.1061	0.162*
C13	0.0185 (7)	−0.2318 (7)	−0.0644 (5)	0.150 (3)
H13A	0.0617	−0.1491	−0.0444	0.225*
H13B	0.0194	−0.2484	−0.1457	0.225*
H13C	0.0767	−0.2905	−0.0245	0.225*
C14	−0.2059 (8)	−0.3789 (5)	−0.0445 (5)	0.127 (2)
H14A	−0.1391	−0.4292	−0.0015	0.190*
H14B	−0.2122	−0.4058	−0.1242	0.190*
H14C	−0.3049	−0.3870	−0.0166	0.190*
C15	−0.1684 (4)	0.2158 (3)	0.3904 (3)	0.0502 (10)
H15	−0.2514	0.1587	0.3915	0.060*
C16	−0.1894 (5)	0.3296 (4)	0.3454 (3)	0.0558 (10)
C17	−0.0668 (5)	0.4172 (3)	0.3430 (3)	0.0534 (10)
C18	0.0714 (5)	0.3827 (3)	0.3861 (3)	0.0528 (10)
C19	0.0856 (4)	0.2666 (3)	0.4299 (3)	0.0502 (10)
H19	0.1805	0.2451	0.4586	0.060*
N1	−0.0336 (3)	0.1850 (3)	0.4321 (3)	0.0455 (7)
O1	0.0614 (3)	−0.0589 (2)	0.3432 (2)	0.0481 (6)
O2	−0.2079 (2)	−0.0639 (2)	0.4225 (2)	0.0433 (6)
Co1	0.0000	0.0000	0.5000	0.04050 (19)
Br1	0.24914 (6)	0.48946 (4)	0.38957 (4)	0.07889 (18)
Br2	−0.08846 (7)	0.57217 (4)	0.28220 (5)	0.0894 (2)
Br3	−0.38542 (6)	0.36046 (5)	0.28797 (6)	0.1058 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.036 (2)	0.0364 (18)	0.044 (2)	0.0044 (15)	0.0030 (17)	0.0021 (16)
C2	0.040 (2)	0.0323 (18)	0.045 (2)	0.0034 (15)	0.0014 (18)	0.0062 (16)
C3	0.047 (2)	0.040 (2)	0.054 (3)	0.0009 (17)	−0.0060 (19)	0.0037 (18)
C4	0.058 (3)	0.054 (2)	0.051 (3)	0.005 (2)	−0.013 (2)	−0.005 (2)
C5	0.066 (3)	0.055 (2)	0.042 (2)	0.013 (2)	−0.004 (2)	−0.0008 (19)
C6	0.058 (3)	0.053 (2)	0.049 (3)	0.012 (2)	0.009 (2)	0.0036 (19)
C7	0.040 (2)	0.064 (3)	0.072 (3)	−0.002 (2)	−0.003 (2)	0.003 (2)
C8	0.043 (2)	0.080 (3)	0.112 (4)	0.016 (2)	0.010 (2)	0.006 (3)
C9	0.052 (3)	0.080 (3)	0.089 (4)	−0.017 (2)	0.015 (2)	0.015 (3)
C10	0.046 (3)	0.128 (5)	0.103 (4)	−0.016 (3)	−0.010 (3)	−0.009 (3)
C11	0.091 (4)	0.097 (4)	0.047 (3)	0.013 (3)	−0.004 (3)	−0.012 (3)
C12	0.134 (5)	0.137 (5)	0.052 (3)	0.017 (4)	−0.010 (3)	0.010 (3)
C13	0.103 (5)	0.278 (10)	0.065 (4)	0.029 (5)	0.021 (4)	−0.066 (5)
C14	0.215 (7)	0.090 (4)	0.069 (4)	0.020 (5)	−0.009 (4)	−0.029 (3)
C15	0.050 (2)	0.045 (2)	0.055 (3)	0.0049 (18)	0.004 (2)	0.0029 (18)
C16	0.062 (3)	0.048 (2)	0.057 (3)	0.016 (2)	0.000 (2)	0.001 (2)
C17	0.074 (3)	0.038 (2)	0.050 (2)	0.012 (2)	0.009 (2)	0.0034 (17)
C18	0.074 (3)	0.038 (2)	0.046 (2)	−0.004 (2)	0.013 (2)	0.0006 (17)
C19	0.053 (2)	0.047 (2)	0.050 (2)	0.0016 (19)	0.0060 (19)	0.0031 (18)
N1	0.0513 (19)	0.0360 (16)	0.0486 (19)	−0.0018 (14)	0.0028 (15)	0.0046 (14)
O1	0.0403 (14)	0.0546 (15)	0.0476 (16)	−0.0005 (12)	−0.0010 (12)	−0.0020 (12)
O2	0.0437 (14)	0.0420 (13)	0.0438 (16)	−0.0005 (11)	0.0036 (12)	0.0014 (11)
Co1	0.0417 (4)	0.0363 (4)	0.0424 (4)	−0.0014 (3)	−0.0002 (3)	0.0020 (3)
Br1	0.0891 (4)	0.0598 (3)	0.0855 (4)	−0.0246 (2)	0.0173 (3)	0.0045 (2)
Br2	0.1427 (5)	0.0459 (3)	0.0827 (4)	0.0210 (3)	0.0061 (3)	0.0203 (2)
Br3	0.0805 (4)	0.0897 (4)	0.1459 (6)	0.0294 (3)	−0.0274 (3)	0.0206 (4)

Geometric parameters (Å, º)

C1—O1	1.274 (4)	C15—N1	1.326 (4)
C1—C6	1.412 (5)	C15—C16	1.377 (5)
C1—C2	1.452 (5)	C16—C17	1.397 (5)
C2—O2	1.290 (4)	C16—Br3	1.873 (4)
C2—C3	1.441 (5)	C17—C18	1.371 (5)
C3—C4	1.369 (5)	C17—Br2	1.863 (4)
C3—C7	1.535 (5)	C18—C19	1.386 (5)
C4—C5	1.421 (5)	C18—Br1	1.888 (4)
C5—C6	1.363 (5)	C19—N1	1.333 (4)
C5—C11	1.531 (6)	N1—Co1	2.214 (3)
C7—C9	1.525 (6)	O1—Co1	2.038 (2)
C7—C10	1.530 (6)	O2—Co1	2.054 (2)
C7—C8	1.533 (6)	Co1—O1^i	2.038 (2)
C11—C14	1.521 (7)	Co1—O2^i	2.054 (2)
C11—C13	1.530 (7)	Co1—N1^i	2.214 (3)
C11—C12	1.548 (7)
O1—C1—C6	122.9 (3)	C17—C16—Br3	122.1 (3)
O1—C1—C2	118.0 (3)	C18—C17—C16	116.5 (3)
C6—C1—C2	119.1 (3)	C18—C17—Br2	121.5 (3)
O2—C2—C3	123.4 (3)	C16—C17—Br2	122.0 (3)
O2—C2—C1	116.5 (3)	C17—C18—C19	120.8 (4)
C3—C2—C1	120.1 (3)	C17—C18—Br1	122.2 (3)
C4—C3—C2	116.0 (3)	C19—C18—Br1	117.1 (3)
C4—C3—C7	123.2 (3)	N1—C19—C18	121.5 (4)
C2—C3—C7	120.8 (3)	C15—N1—C19	119.0 (3)
C3—C4—C5	125.1 (4)	C15—N1—Co1	121.8 (2)
C6—C5—C4	118.6 (4)	C19—N1—Co1	119.2 (3)
C6—C5—C11	122.1 (4)	C1—O1—Co1	113.0 (2)
C4—C5—C11	119.4 (4)	C2—O2—Co1	112.7 (2)
C5—C6—C1	121.1 (4)	O1—Co1—O1^i	180.0
C9—C7—C10	108.1 (4)	O1—Co1—O2^i	100.16 (9)
C9—C7—C8	110.1 (4)	O1^i—Co1—O2^i	79.84 (9)
C10—C7—C8	108.4 (4)	O1—Co1—O2	79.84 (9)
C9—C7—C3	110.0 (3)	O1^i—Co1—O2	100.16 (9)
C10—C7—C3	111.3 (4)	O2^i—Co1—O2	180.0
C8—C7—C3	108.9 (3)	O1—Co1—N1^i	90.99 (10)
C14—C11—C13	109.7 (5)	O1^i—Co1—N1^i	89.01 (10)
C14—C11—C5	109.7 (4)	O2^i—Co1—N1^i	89.40 (10)
C13—C11—C5	112.3 (4)	O2—Co1—N1^i	90.60 (10)
C14—C11—C12	108.6 (4)	O1—Co1—N1	89.01 (10)
C13—C11—C12	107.7 (5)	O1^i—Co1—N1	90.99 (10)
C5—C11—C12	108.8 (4)	O2^i—Co1—N1	90.60 (10)
N1—C15—C16	122.1 (4)	O2—Co1—N1	89.40 (10)
C15—C16—C17	120.2 (4)	N1^i—Co1—N1	180.0
C15—C16—Br3	117.7 (3)
O1—C1—C2—O2	1.0 (4)	C6—C5—C11—C13	−0.3 (7)
C6—C1—C2—O2	−179.8 (3)	C4—C5—C11—C13	179.1 (5)
O1—C1—C2—C3	−178.7 (3)	C6—C5—C11—C12	−119.4 (5)
C6—C1—C2—C3	0.4 (5)	C4—C5—C11—C12	60.0 (6)
O2—C2—C3—C4	179.7 (3)	N1—C15—C16—C17	−0.2 (6)
C1—C2—C3—C4	−0.5 (5)	N1—C15—C16—Br3	179.4 (3)
O2—C2—C3—C7	0.1 (5)	C15—C16—C17—C18	0.6 (6)
C1—C2—C3—C7	179.9 (3)	Br3—C16—C17—C18	−179.0 (3)
C2—C3—C4—C5	0.8 (6)	C15—C16—C17—Br2	179.5 (3)
C7—C3—C4—C5	−179.6 (4)	Br3—C16—C17—Br2	0.0 (5)
C3—C4—C5—C6	−1.0 (6)	C16—C17—C18—C19	−0.4 (6)
C3—C4—C5—C11	179.5 (4)	Br2—C17—C18—C19	−179.4 (3)
C4—C5—C6—C1	0.9 (6)	C16—C17—C18—Br1	−180.0 (3)
C11—C5—C6—C1	−179.7 (4)	Br2—C17—C18—Br1	1.0 (5)
O1—C1—C6—C5	178.5 (3)	C17—C18—C19—N1	−0.1 (6)
C2—C1—C6—C5	−0.6 (5)	Br1—C18—C19—N1	179.5 (3)
C4—C3—C7—C9	122.6 (4)	C16—C15—N1—C19	−0.3 (5)
C2—C3—C7—C9	−57.8 (5)	C16—C15—N1—Co1	−178.4 (3)
C4—C3—C7—C10	2.9 (6)	C18—C19—N1—C15	0.5 (5)
C2—C3—C7—C10	−177.6 (4)	C18—C19—N1—Co1	178.6 (3)
C4—C3—C7—C8	−116.6 (4)	C6—C1—O1—Co1	179.1 (3)
C2—C3—C7—C8	63.0 (5)	C2—C1—O1—Co1	−1.7 (4)
C6—C5—C11—C14	122.0 (5)	C3—C2—O2—Co1	180.0 (3)
C4—C5—C11—C14	−58.6 (6)	C1—C2—O2—Co1	0.2 (3)

Symmetry code: (i) −x, −y, −z+1.

(4_100K)

Crystal data

C38H44Cl6CoN2O4	Z = 1
Mr = 864.38	F(000) = 447
Triclinic, P1	Dx = 1.355 Mg m^−3
a = 8.7762 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5578 (4) Å	Cell parameters from 20609 reflections
c = 11.4878 (5) Å	θ = 2.3–26.0°
α = 91.565 (3)°	µ = 0.82 mm^−1
β = 93.882 (2)°	T = 100 K
γ = 93.950 (4)°	Block, blue
V = 1058.92 (7) Å^3	0.23 × 0.20 × 0.16 mm

Data collection

SuperNova, Single source at offset), Atlas diffractometer	4160 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2864 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.066
ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.35 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'	h = −10→10
Tmin = 0.833, Tmax = 0.880	k = −13→13
20609 measured reflections	l = −14→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0392P)^2 + 1.9348P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
4160 reflections	Δρmax = 0.70 e Å^−3
238 parameters	Δρmin = −0.34 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.5502 (4)	0.0988 (3)	0.7292 (3)	0.0220 (8)
C2	0.7024 (4)	0.1068 (3)	0.6829 (3)	0.0221 (8)
C3	0.8332 (4)	0.1586 (3)	0.7555 (3)	0.0231 (8)
C4	0.8061 (4)	0.2001 (3)	0.8665 (3)	0.0258 (8)
H4	0.8912	0.2353	0.9151	0.031*
C5	0.6584 (4)	0.1940 (3)	0.9143 (3)	0.0256 (8)
C6	0.5342 (4)	0.1426 (3)	0.8450 (3)	0.0249 (8)
H6	0.4361	0.1363	0.8754	0.030*
C7	0.9935 (4)	0.1664 (3)	0.7089 (3)	0.0272 (8)
C8	0.9955 (4)	0.2473 (4)	0.5994 (3)	0.0303 (9)
H8A	0.9591	0.3308	0.6174	0.045*
H8B	0.9285	0.2047	0.5364	0.045*
H8C	1.1002	0.2579	0.5747	0.045*
C9	1.0370 (4)	0.0311 (4)	0.6780 (4)	0.0330 (9)
H9A	1.1424	0.0347	0.6544	0.050*
H9B	0.9674	−0.0056	0.6137	0.050*
H9C	1.0289	−0.0218	0.7464	0.050*
C10	1.1146 (4)	0.2270 (4)	0.7997 (4)	0.0378 (10)
H10A	1.0869	0.3121	0.8223	0.057*
H10B	1.2146	0.2333	0.7662	0.057*
H10C	1.1199	0.1744	0.8686	0.057*
C11	0.6455 (4)	0.2468 (4)	1.0383 (3)	0.0319 (9)
C12	0.7501 (5)	0.1782 (4)	1.1247 (4)	0.0400 (10)
H12A	0.8560	0.1892	1.1026	0.060*
H12B	0.7173	0.0875	1.1230	0.060*
H12C	0.7438	0.2142	1.2036	0.060*
C13	0.4810 (5)	0.2291 (5)	1.0769 (4)	0.0444 (11)
H13A	0.4784	0.2619	1.1574	0.067*
H13B	0.4471	0.1386	1.0728	0.067*
H13C	0.4126	0.2755	1.0253	0.067*
C14	0.6962 (5)	0.3890 (4)	1.0430 (4)	0.0436 (11)
H14A	0.6921	0.4232	1.1228	0.065*
H14B	0.6276	0.4337	0.9900	0.065*
H14C	0.8012	0.4010	1.0191	0.065*
C15	0.5815 (4)	0.2739 (3)	0.4284 (3)	0.0256 (8)
H15	0.6804	0.2510	0.4551	0.031*
C16	0.5663 (4)	0.3940 (3)	0.3853 (3)	0.0273 (8)
C17	0.4234 (5)	0.4288 (3)	0.3450 (3)	0.0289 (9)
C18	0.2996 (4)	0.3394 (3)	0.3506 (3)	0.0285 (8)
C19	0.3240 (4)	0.2215 (3)	0.3950 (3)	0.0252 (8)
H19	0.2391	0.1611	0.3979	0.030*
N1	0.4627 (3)	0.1893 (3)	0.4338 (3)	0.0239 (7)
O1	0.4369 (3)	0.0530 (2)	0.6608 (2)	0.0252 (6)
O2	0.7091 (3)	0.0656 (2)	0.5762 (2)	0.0232 (5)
Cl1	0.11666 (12)	0.37263 (10)	0.30215 (10)	0.0451 (3)
Cl2	0.40023 (14)	0.57621 (9)	0.28883 (9)	0.0442 (3)
Cl3	0.72867 (12)	0.49668 (9)	0.38213 (9)	0.0388 (3)
Co1	0.5000	0.0000	0.5000	0.02276 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0207 (18)	0.0179 (17)	0.027 (2)	0.0021 (14)	−0.0033 (15)	0.0044 (14)
C2	0.0225 (18)	0.0167 (17)	0.027 (2)	0.0009 (14)	−0.0004 (15)	0.0048 (15)
C3	0.0200 (18)	0.0196 (18)	0.029 (2)	0.0012 (14)	−0.0024 (15)	0.0047 (15)
C4	0.0214 (19)	0.0232 (19)	0.032 (2)	0.0007 (14)	−0.0039 (16)	0.0006 (16)
C5	0.028 (2)	0.0240 (19)	0.025 (2)	0.0045 (15)	0.0018 (16)	0.0038 (15)
C6	0.0191 (18)	0.0239 (19)	0.032 (2)	0.0025 (14)	0.0027 (16)	0.0048 (15)
C7	0.0167 (18)	0.030 (2)	0.033 (2)	−0.0034 (15)	−0.0019 (16)	0.0007 (16)
C8	0.0185 (19)	0.035 (2)	0.036 (2)	−0.0075 (15)	0.0023 (16)	0.0033 (17)
C9	0.0173 (19)	0.037 (2)	0.045 (3)	0.0050 (16)	0.0013 (17)	0.0019 (18)
C10	0.023 (2)	0.049 (3)	0.040 (3)	−0.0042 (18)	−0.0020 (18)	−0.002 (2)
C11	0.032 (2)	0.034 (2)	0.029 (2)	0.0015 (17)	0.0000 (17)	−0.0015 (17)
C12	0.039 (2)	0.050 (3)	0.030 (2)	−0.0004 (19)	−0.0028 (19)	0.0042 (19)
C13	0.033 (2)	0.069 (3)	0.031 (2)	0.005 (2)	0.0045 (19)	−0.010 (2)
C14	0.054 (3)	0.045 (3)	0.031 (2)	0.004 (2)	0.004 (2)	−0.0040 (19)
C15	0.026 (2)	0.030 (2)	0.0203 (19)	−0.0017 (15)	0.0010 (15)	−0.0010 (15)
C16	0.031 (2)	0.030 (2)	0.020 (2)	−0.0053 (16)	0.0017 (16)	−0.0021 (15)
C17	0.043 (2)	0.0221 (19)	0.022 (2)	0.0035 (16)	0.0038 (17)	−0.0002 (15)
C18	0.027 (2)	0.030 (2)	0.028 (2)	0.0062 (16)	−0.0031 (16)	−0.0007 (16)
C19	0.0230 (19)	0.0257 (19)	0.027 (2)	0.0023 (15)	0.0035 (16)	0.0001 (15)
N1	0.0222 (16)	0.0233 (16)	0.0255 (17)	−0.0013 (12)	0.0004 (13)	0.0019 (13)
O1	0.0190 (13)	0.0281 (13)	0.0282 (14)	0.0004 (10)	−0.0012 (11)	0.0026 (11)
O2	0.0180 (12)	0.0247 (13)	0.0265 (15)	−0.0002 (10)	0.0002 (10)	0.0004 (10)
Cl1	0.0359 (6)	0.0425 (6)	0.0574 (7)	0.0145 (5)	−0.0069 (5)	0.0071 (5)
Cl2	0.0692 (8)	0.0242 (5)	0.0397 (6)	0.0080 (5)	−0.0003 (5)	0.0077 (4)
Cl3	0.0436 (6)	0.0316 (5)	0.0391 (6)	−0.0147 (4)	0.0054 (5)	0.0008 (4)
Co1	0.0180 (4)	0.0224 (4)	0.0272 (4)	−0.0009 (3)	−0.0013 (3)	0.0011 (3)

Geometric parameters (Å, º)

C1—O1	1.284 (4)	C15—N1	1.331 (4)
C1—C6	1.415 (5)	C15—C16	1.385 (5)
C1—C2	1.469 (5)	C16—C17	1.384 (5)
C2—O2	1.295 (4)	C16—Cl3	1.733 (4)
C2—C3	1.439 (5)	C17—C18	1.395 (5)
C3—C4	1.377 (5)	C17—Cl2	1.720 (4)
C3—C7	1.537 (5)	C18—C19	1.383 (5)
C4—C5	1.439 (5)	C18—Cl1	1.726 (4)
C5—C6	1.376 (5)	C19—N1	1.337 (4)
C5—C11	1.530 (5)	N1—Co1	2.195 (3)
C7—C10	1.532 (5)	O1—Co1	2.038 (2)
C7—C8	1.540 (5)	O2—Co1	2.047 (2)
C7—C9	1.542 (5)	Co1—O1^i	2.038 (2)
C11—C14	1.535 (6)	Co1—O2^i	2.047 (2)
C11—C12	1.536 (5)	Co1—N1^i	2.195 (3)
C11—C13	1.540 (5)
O1—C1—C6	123.1 (3)	C15—C16—Cl3	118.6 (3)
O1—C1—C2	117.5 (3)	C16—C17—C18	117.4 (3)
C6—C1—C2	119.4 (3)	C16—C17—Cl2	121.1 (3)
O2—C2—C3	123.9 (3)	C18—C17—Cl2	121.4 (3)
O2—C2—C1	116.3 (3)	C19—C18—C17	119.4 (3)
C3—C2—C1	119.8 (3)	C19—C18—Cl1	119.3 (3)
C4—C3—C2	116.7 (3)	C17—C18—Cl1	121.3 (3)
C4—C3—C7	122.9 (3)	N1—C19—C18	122.4 (3)
C2—C3—C7	120.5 (3)	C15—N1—C19	118.5 (3)
C3—C4—C5	124.9 (3)	C15—N1—Co1	119.5 (2)
C6—C5—C4	118.1 (3)	C19—N1—Co1	121.9 (2)
C6—C5—C11	122.9 (3)	C1—O1—Co1	112.9 (2)
C4—C5—C11	119.0 (3)	C2—O2—Co1	112.9 (2)
C5—C6—C1	121.1 (3)	O1^i—Co1—O1	180.00 (5)
C10—C7—C3	111.6 (3)	O1^i—Co1—O2^i	80.35 (9)
C10—C7—C8	107.9 (3)	O1—Co1—O2^i	99.65 (9)
C3—C7—C8	110.3 (3)	O1^i—Co1—O2	99.65 (9)
C10—C7—C9	108.4 (3)	O1—Co1—O2	80.35 (9)
C3—C7—C9	109.0 (3)	O2^i—Co1—O2	180.00 (14)
C8—C7—C9	109.6 (3)	O1^i—Co1—N1	88.84 (10)
C5—C11—C14	108.7 (3)	O1—Co1—N1	91.16 (10)
C5—C11—C12	109.9 (3)	O2^i—Co1—N1	89.50 (10)
C14—C11—C12	109.1 (3)	O2—Co1—N1	90.50 (10)
C5—C11—C13	112.2 (3)	O1^i—Co1—N1^i	91.16 (10)
C14—C11—C13	109.0 (3)	O1—Co1—N1^i	88.84 (10)
C12—C11—C13	107.9 (3)	O2^i—Co1—N1^i	90.50 (10)
N1—C15—C16	122.4 (3)	O2—Co1—N1^i	89.50 (10)
C17—C16—C15	119.7 (3)	N1—Co1—N1^i	180.0
C17—C16—Cl3	121.6 (3)
O1—C1—C2—O2	−0.5 (4)	C6—C5—C11—C12	122.9 (4)
C6—C1—C2—O2	−179.8 (3)	C4—C5—C11—C12	−58.2 (4)
O1—C1—C2—C3	179.4 (3)	C6—C5—C11—C13	2.8 (5)
C6—C1—C2—C3	0.1 (5)	C4—C5—C11—C13	−178.3 (3)
O2—C2—C3—C4	179.0 (3)	N1—C15—C16—C17	−0.6 (5)
C1—C2—C3—C4	−0.9 (4)	N1—C15—C16—Cl3	180.0 (3)
O2—C2—C3—C7	−0.7 (5)	C15—C16—C17—C18	0.3 (5)
C1—C2—C3—C7	179.4 (3)	Cl3—C16—C17—C18	179.7 (3)
C2—C3—C4—C5	0.7 (5)	C15—C16—C17—Cl2	−179.1 (3)
C7—C3—C4—C5	−179.6 (3)	Cl3—C16—C17—Cl2	0.3 (5)
C3—C4—C5—C6	0.3 (5)	C16—C17—C18—C19	−0.2 (5)
C3—C4—C5—C11	−178.6 (3)	Cl2—C17—C18—C19	179.1 (3)
C4—C5—C6—C1	−1.1 (5)	C16—C17—C18—Cl1	−179.7 (3)
C11—C5—C6—C1	177.8 (3)	Cl2—C17—C18—Cl1	−0.3 (5)
O1—C1—C6—C5	−178.3 (3)	C17—C18—C19—N1	0.4 (6)
C2—C1—C6—C5	0.9 (5)	Cl1—C18—C19—N1	179.9 (3)
C4—C3—C7—C10	−0.9 (5)	C16—C15—N1—C19	0.7 (5)
C2—C3—C7—C10	178.8 (3)	C16—C15—N1—Co1	178.6 (3)
C4—C3—C7—C8	−120.8 (4)	C18—C19—N1—C15	−0.7 (5)
C2—C3—C7—C8	58.9 (4)	C18—C19—N1—Co1	−178.5 (3)
C4—C3—C7—C9	118.8 (4)	C6—C1—O1—Co1	179.7 (2)
C2—C3—C7—C9	−61.5 (4)	C2—C1—O1—Co1	0.5 (3)
C6—C5—C11—C14	−117.8 (4)	C3—C2—O2—Co1	−179.6 (2)
C4—C5—C11—C14	61.1 (4)	C1—C2—O2—Co1	0.3 (3)

Symmetry code: (i) −x+1, −y, −z+1.