Di­chloro­{methyl 4-[(1,4,7,10-tetra­aza­cyclo­dodec-1-yl)­methyl]­benzoate}­cobalt(III) methylsulfate

The title compound, [CoCl₂(C₁₇H₂₈N₄O₂)](CH₃O₄S), is formed from the esterification of the parent benzoic acid complex in refluxing methanol/sulfuric acid. The coordination around cobalt is distorted octahedral, with cis chloride ligands.

Key indicators

• Single-crystal X-ray study
• T = 103 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.034
• wR factor = 0.098
• Data-to-parameter ratio = 19.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.80 Ratio

Author Response: The largest Ueq's are in the region of C20 to C23. This terminal group off of a phenyl ring doesn't interact with any other atoms in the crystal structure. Thus even in this low temperature structure the thermal paramertes increase towards the end of this chain although the elipsoids themselves are not disotted and have resonable orientations.

PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       6.12 Ratio

Author Response: (see above) these are the riding hydrogens on C23 in the group described above.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.99
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.61 mm
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co     -   Cl1      =       6.90 su
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          3

   2 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 2000), XPREP (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

(I)

Crystal data

[Co(C17H28N4O2)Cl2]·CH3O4S	Z = 2
Mr = 561.37	F(000) = 584
Triclinic, P1	Dx = 1.561 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0250 (5) Å	Cell parameters from 8842 reflections
b = 8.2310 (5) Å	θ = 2.2–29.0°
c = 18.7105 (11) Å	µ = 1.07 mm^−1
α = 79.067 (1)°	T = 103 K
β = 80.884 (1)°	Prism, purple
γ = 83.636 (1)°	0.61 × 0.20 × 0.18 mm
V = 1193.97 (13) Å^3

Data collection

Bruker SMART 1000 CCD diffractometer	5701 independent reflections
Radiation source: sealed tube	5017 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 29.0°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→9
Tmin = 0.695, Tmax = 0.824	k = −11→10
12393 measured reflections	l = −24→25

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ^2(Fo^2) + (0.0608P)^2 + 0.977P] where P = (Fo^2 + 2Fc^2)/3
5700 reflections	(Δ/σ)max = 0.001
300 parameters	Δρmax = 0.89 e Å^−3
0 restraints	Δρmin = −0.50 e Å^−3

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Co	0.45115 (3)	0.57761 (3)	0.144491 (13)	0.01273 (8)
Cl1	0.24456 (6)	0.69652 (6)	0.07504 (3)	0.02035 (11)
Cl2	0.39295 (6)	0.32742 (6)	0.12132 (2)	0.01755 (11)
N1	0.3089 (2)	0.5669 (2)	0.24589 (9)	0.0156 (3)
C2	0.3092 (3)	0.7336 (2)	0.27026 (11)	0.0198 (4)
H2A	0.1967	0.7631	0.2971	0.024*
H2B	0.3947	0.7257	0.3038	0.024*
C3	0.3498 (3)	0.8659 (2)	0.20382 (11)	0.0207 (4)
H3A	0.2529	0.8933	0.1756	0.025*
H3B	0.3763	0.9681	0.2188	0.025*
N4	0.4989 (2)	0.7945 (2)	0.15915 (9)	0.0170 (3)
H4	0.585 (3)	0.790 (3)	0.1837 (14)	0.020*
C5	0.5508 (3)	0.8970 (2)	0.08651 (11)	0.0214 (4)
H5A	0.5973	0.9993	0.0925	0.026*
H5B	0.4528	0.9289	0.0591	0.026*
C6	0.6849 (3)	0.7900 (3)	0.04603 (12)	0.0219 (4)
H6A	0.6977	0.8349	−0.0073	0.026*
H6B	0.7951	0.7912	0.0633	0.026*
N7	0.6345 (2)	0.6139 (2)	0.05972 (9)	0.0170 (3)
H7	0.602 (3)	0.600 (3)	0.0198 (15)	0.020*
C8	0.7821 (2)	0.4934 (3)	0.07730 (11)	0.0202 (4)
H8A	0.8871	0.5309	0.0461	0.024*
H8B	0.7643	0.3824	0.0682	0.024*
C9	0.7968 (2)	0.4851 (2)	0.15789 (11)	0.0177 (4)
H9A	0.8830	0.3960	0.1742	0.021*
H9B	0.8282	0.5921	0.1665	0.021*
N10	0.6262 (2)	0.4491 (2)	0.19742 (9)	0.0143 (3)
H10	0.615 (3)	0.356 (3)	0.1919 (14)	0.017*
C11	0.5895 (2)	0.4546 (2)	0.27718 (10)	0.0167 (4)
H11A	0.6168	0.5618	0.2872	0.020*
H11B	0.6554	0.3631	0.3057	0.020*
C12	0.4006 (2)	0.4351 (2)	0.29650 (10)	0.0171 (4)
H12A	0.3764	0.3235	0.2905	0.021*
H12B	0.3622	0.4474	0.3483	0.021*
C13	0.1297 (2)	0.5284 (3)	0.24569 (11)	0.0204 (4)
H13A	0.1330	0.4437	0.2142	0.025*
H13B	0.0672	0.6302	0.2226	0.025*
C14	0.0302 (3)	0.4660 (3)	0.32012 (11)	0.0211 (4)
C15	0.0191 (3)	0.2959 (3)	0.34254 (13)	0.0282 (5)
H15A	0.0833	0.2214	0.3136	0.034*
C16	−0.0842 (3)	0.2326 (3)	0.40668 (14)	0.0336 (5)
H16A	−0.0914	0.1162	0.4208	0.040*
C17	−0.1766 (3)	0.3404 (3)	0.44990 (12)	0.0301 (5)
C18	−0.1645 (3)	0.5114 (3)	0.42879 (12)	0.0280 (5)
H18A	−0.2260	0.5854	0.4587	0.034*
C19	−0.0628 (3)	0.5736 (3)	0.36423 (12)	0.0249 (4)
H19A	−0.0564	0.6901	0.3500	0.030*
C20	−0.2973 (4)	0.2804 (4)	0.51714 (13)	0.0379 (6)
O21	−0.3696 (3)	0.3664 (3)	0.55986 (10)	0.0427 (5)
O22	−0.3185 (3)	0.1178 (3)	0.52328 (12)	0.0619 (7)
C23	−0.4380 (6)	0.0445 (6)	0.5876 (2)	0.0802 (14)
H23A	−0.4580	−0.0677	0.5823	0.104*
H23B	−0.5456	0.1138	0.5898	0.104*
H23C	−0.3892	0.0393	0.6328	0.104*
S	0.81037 (7)	−0.00403 (6)	0.23169 (3)	0.02219 (12)
O1	0.9664 (2)	0.0071 (2)	0.25846 (10)	0.0321 (4)
O2	0.6594 (2)	0.0750 (2)	0.26772 (10)	0.0337 (4)
O3	0.7910 (2)	−0.17199 (18)	0.22117 (10)	0.0291 (4)
O4	0.82127 (19)	0.10897 (19)	0.15025 (9)	0.0262 (3)
C4A	0.9755 (3)	0.0833 (3)	0.10085 (14)	0.0303 (5)
H4AA	0.9591	0.1363	0.0507	0.039*
H4AB	1.0047	−0.0360	0.1025	0.039*
H4AC	1.0675	0.1322	0.1159	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co	0.01322 (13)	0.01300 (13)	0.01269 (13)	0.00030 (9)	−0.00398 (9)	−0.00304 (9)
Cl1	0.0198 (2)	0.0243 (2)	0.0178 (2)	0.00428 (18)	−0.00830 (17)	−0.00447 (17)
Cl2	0.0198 (2)	0.0169 (2)	0.0182 (2)	−0.00360 (17)	−0.00524 (17)	−0.00556 (16)
N1	0.0139 (7)	0.0193 (8)	0.0145 (7)	−0.0005 (6)	−0.0039 (6)	−0.0044 (6)
C2	0.0227 (10)	0.0196 (9)	0.0187 (9)	0.0018 (7)	−0.0046 (7)	−0.0080 (7)
C3	0.0223 (10)	0.0170 (9)	0.0227 (10)	0.0025 (7)	−0.0028 (8)	−0.0061 (7)
N4	0.0197 (8)	0.0147 (7)	0.0165 (8)	0.0004 (6)	−0.0037 (6)	−0.0028 (6)
C5	0.0266 (10)	0.0153 (9)	0.0214 (10)	−0.0032 (8)	−0.0030 (8)	−0.0005 (7)
C6	0.0252 (10)	0.0191 (9)	0.0213 (10)	−0.0060 (8)	−0.0016 (8)	−0.0021 (7)
N7	0.0187 (8)	0.0184 (8)	0.0150 (8)	−0.0035 (6)	−0.0027 (6)	−0.0040 (6)
C8	0.0172 (9)	0.0221 (10)	0.0218 (9)	0.0005 (7)	−0.0014 (7)	−0.0075 (8)
C9	0.0141 (8)	0.0181 (9)	0.0221 (9)	−0.0004 (7)	−0.0039 (7)	−0.0060 (7)
N10	0.0155 (7)	0.0125 (7)	0.0166 (7)	0.0002 (6)	−0.0053 (6)	−0.0049 (6)
C11	0.0177 (9)	0.0168 (9)	0.0170 (9)	0.0002 (7)	−0.0072 (7)	−0.0036 (7)
C12	0.0186 (9)	0.0176 (9)	0.0155 (9)	−0.0009 (7)	−0.0054 (7)	−0.0015 (7)
C13	0.0139 (9)	0.0309 (11)	0.0180 (9)	−0.0023 (8)	−0.0032 (7)	−0.0072 (8)
C14	0.0168 (9)	0.0296 (11)	0.0187 (9)	−0.0035 (8)	−0.0040 (7)	−0.0065 (8)
C15	0.0269 (11)	0.0298 (11)	0.0298 (11)	−0.0062 (9)	0.0021 (9)	−0.0130 (9)
C16	0.0369 (13)	0.0302 (12)	0.0331 (13)	−0.0116 (10)	0.0018 (10)	−0.0044 (10)
C17	0.0315 (12)	0.0413 (13)	0.0189 (10)	−0.0110 (10)	−0.0015 (9)	−0.0058 (9)
C18	0.0274 (11)	0.0374 (12)	0.0191 (10)	−0.0008 (9)	−0.0001 (8)	−0.0088 (9)
C19	0.0232 (10)	0.0294 (11)	0.0208 (10)	0.0007 (8)	−0.0017 (8)	−0.0041 (8)
C20	0.0422 (14)	0.0529 (16)	0.0209 (11)	−0.0204 (12)	−0.0012 (10)	−0.0052 (11)
O21	0.0456 (11)	0.0612 (13)	0.0201 (8)	−0.0124 (9)	0.0050 (8)	−0.0076 (8)
O22	0.0860 (18)	0.0648 (15)	0.0366 (11)	−0.0461 (14)	0.0195 (11)	−0.0131 (10)
C23	0.115 (4)	0.085 (3)	0.0444 (19)	−0.061 (3)	0.014 (2)	−0.0116 (19)
S	0.0225 (2)	0.0147 (2)	0.0313 (3)	0.00114 (18)	−0.0075 (2)	−0.00744 (19)
O1	0.0292 (9)	0.0314 (9)	0.0415 (10)	−0.0011 (7)	−0.0137 (7)	−0.0144 (7)
O2	0.0296 (9)	0.0227 (8)	0.0449 (10)	0.0037 (7)	0.0014 (7)	−0.0048 (7)
O3	0.0359 (9)	0.0145 (7)	0.0415 (9)	0.0002 (6)	−0.0188 (7)	−0.0065 (6)
O4	0.0220 (7)	0.0204 (7)	0.0338 (9)	0.0043 (6)	−0.0045 (6)	−0.0020 (6)
C4A	0.0250 (11)	0.0308 (12)	0.0335 (12)	0.0060 (9)	−0.0031 (9)	−0.0071 (9)

Geometric parameters (Å, º)

Co—N4	1.9444 (17)	C11—C12	1.520 (3)
Co—N10	1.9462 (16)	C11—H11A	0.9900
Co—N7	1.9868 (17)	C11—H11B	0.9900
Co—N1	2.0453 (16)	C12—H12A	0.9900
Co—Cl1	2.2882 (5)	C12—H12B	0.9900
Co—Cl2	2.2940 (5)	C13—C14	1.519 (3)
N1—C12	1.507 (2)	C13—H13A	0.9900
N1—C13	1.507 (2)	C13—H13B	0.9900
N1—C2	1.526 (2)	C14—C15	1.392 (3)
C2—C3	1.508 (3)	C14—C19	1.399 (3)
C2—H2A	0.9900	C15—C16	1.394 (3)
C2—H2B	0.9900	C15—H15A	0.9500
C3—N4	1.480 (3)	C16—C17	1.389 (4)
C3—H3A	0.9900	C16—H16A	0.9500
C3—H3B	0.9900	C17—C18	1.398 (3)
N4—C5	1.482 (2)	C17—C20	1.500 (3)
N4—H4	0.88 (3)	C18—C19	1.390 (3)
C5—C6	1.515 (3)	C18—H18A	0.9500
C5—H5A	0.9900	C19—H19A	0.9500
C5—H5B	0.9900	C20—O21	1.205 (3)
C6—N7	1.512 (3)	C20—O22	1.349 (4)
C6—H6A	0.9900	O22—C23	1.489 (4)
C6—H6B	0.9900	C23—H23A	0.9800
N7—C8	1.495 (3)	C23—H23B	0.9800
N7—H7	0.86 (3)	C23—H23C	0.9800
C8—C9	1.519 (3)	S—O1	1.4384 (17)
C8—H8A	0.9900	S—O2	1.4418 (17)
C8—H8B	0.9900	S—O3	1.4611 (15)
C9—N10	1.481 (2)	S—O4	1.6226 (17)
C9—H9A	0.9900	O4—C4A	1.444 (3)
C9—H9B	0.9900	C4A—H4AA	0.9800
N10—C11	1.483 (2)	C4A—H4AB	0.9800
N10—H10	0.81 (3)	C4A—H4AC	0.9800
N4—Co—N10	96.74 (7)	C8—C9—H9B	110.8
N4—Co—N7	83.89 (7)	H9A—C9—H9B	108.9
N10—Co—N7	85.46 (7)	C9—N10—C11	118.87 (15)
N4—Co—N1	84.23 (7)	C9—N10—Co	110.64 (12)
N10—Co—N1	85.19 (7)	C11—N10—Co	111.37 (12)
N7—Co—N1	163.90 (7)	C9—N10—H10	104.5 (18)
N4—Co—Cl1	90.92 (5)	C11—N10—H10	108.1 (18)
N10—Co—Cl1	171.96 (5)	Co—N10—H10	101.6 (18)
N7—Co—Cl1	92.97 (5)	N10—C11—C12	104.35 (15)
N1—Co—Cl1	98.06 (5)	N10—C11—H11A	110.9
N4—Co—Cl2	177.16 (5)	C12—C11—H11A	110.9
N10—Co—Cl2	85.40 (5)	N10—C11—H11B	110.9
N7—Co—Cl2	94.45 (5)	C12—C11—H11B	110.9
N1—Co—Cl2	97.82 (5)	H11A—C11—H11B	108.9
Cl1—Co—Cl2	86.867 (19)	N1—C12—C11	108.26 (15)
C12—N1—C13	111.78 (15)	N1—C12—H12A	110.0
C12—N1—C2	108.72 (14)	C11—C12—H12A	110.0
C13—N1—C2	110.13 (15)	N1—C12—H12B	110.0
C12—N1—Co	105.53 (11)	C11—C12—H12B	110.0
C13—N1—Co	112.33 (12)	H12A—C12—H12B	108.4
C2—N1—Co	108.16 (12)	N1—C13—C14	116.35 (16)
C3—C2—N1	109.59 (16)	N1—C13—H13A	108.2
C3—C2—H2A	109.8	C14—C13—H13A	108.2
N1—C2—H2A	109.8	N1—C13—H13B	108.2
C3—C2—H2B	109.8	C14—C13—H13B	108.2
N1—C2—H2B	109.8	H13A—C13—H13B	107.4
H2A—C2—H2B	108.2	C15—C14—C19	118.5 (2)
N4—C3—C2	105.58 (16)	C15—C14—C13	118.8 (2)
N4—C3—H3A	110.6	C19—C14—C13	122.42 (19)
C2—C3—H3A	110.6	C14—C15—C16	121.3 (2)
N4—C3—H3B	110.6	C14—C15—H15A	119.3
C2—C3—H3B	110.6	C16—C15—H15A	119.3
H3A—C3—H3B	108.8	C17—C16—C15	119.7 (2)
C3—N4—C5	115.03 (16)	C17—C16—H16A	120.1
C3—N4—Co	108.64 (12)	C15—C16—H16A	120.1
C5—N4—Co	108.85 (13)	C16—C17—C18	119.7 (2)
C3—N4—H4	106.0 (16)	C16—C17—C20	122.1 (2)
C5—N4—H4	105.1 (16)	C18—C17—C20	118.2 (2)
Co—N4—H4	113.3 (16)	C19—C18—C17	120.3 (2)
N4—C5—C6	105.98 (16)	C19—C18—H18A	119.9
N4—C5—H5A	110.5	C17—C18—H18A	119.9
C6—C5—H5A	110.5	C18—C19—C14	120.5 (2)
N4—C5—H5B	110.5	C18—C19—H19A	119.7
C6—C5—H5B	110.5	C14—C19—H19A	119.7
H5A—C5—H5B	108.7	O21—C20—O22	123.7 (2)
N7—C6—C5	109.69 (16)	O21—C20—C17	124.7 (3)
N7—C6—H6A	109.7	O22—C20—C17	111.5 (2)
C5—C6—H6A	109.7	C20—O22—C23	116.4 (3)
N7—C6—H6B	109.7	O22—C23—H23A	109.5
C5—C6—H6B	109.7	O22—C23—H23B	109.5
H6A—C6—H6B	108.2	H23A—C23—H23B	109.5
C8—N7—C6	110.29 (15)	O22—C23—H23C	109.5
C8—N7—Co	107.62 (12)	H23A—C23—H23C	109.5
C6—N7—Co	110.91 (13)	H23B—C23—H23C	109.5
C8—N7—H7	110.6 (17)	O1—S—O2	116.68 (11)
C6—N7—H7	106.1 (16)	O1—S—O3	112.35 (10)
Co—N7—H7	111.4 (17)	O2—S—O3	113.77 (10)
N7—C8—C9	107.48 (16)	O1—S—O4	106.74 (10)
N7—C8—H8A	110.2	O2—S—O4	100.20 (9)
C9—C8—H8A	110.2	O3—S—O4	105.40 (9)
N7—C8—H8B	110.2	C4A—O4—S	116.14 (13)
C9—C8—H8B	110.2	O4—C4A—H4AA	109.5
H8A—C8—H8B	108.5	O4—C4A—H4AB	109.5
N10—C9—C8	104.77 (15)	H4AA—C4A—H4AB	109.5
N10—C9—H9A	110.8	O4—C4A—H4AC	109.5
C8—C9—H9A	110.8	H4AA—C4A—H4AC	109.5
N10—C9—H9B	110.8	H4AB—C4A—H4AC	109.5
N4—Co—N1—C12	−111.33 (12)	Cl2—Co—N7—C6	168.16 (12)
N10—Co—N1—C12	−14.04 (12)	C6—N7—C8—C9	80.84 (19)
N7—Co—N1—C12	−68.7 (3)	Co—N7—C8—C9	−40.27 (17)
Cl1—Co—N1—C12	158.56 (11)	N7—C8—C9—N10	52.88 (19)
Cl2—Co—N1—C12	70.64 (11)	C8—C9—N10—C11	−172.00 (16)
N4—Co—N1—C13	126.64 (14)	C8—C9—N10—Co	−41.28 (17)
N10—Co—N1—C13	−136.07 (14)	N4—Co—N10—C9	−67.28 (13)
N7—Co—N1—C13	169.3 (2)	N7—Co—N10—C9	16.00 (13)
Cl1—Co—N1—C13	36.52 (13)	N1—Co—N10—C9	−150.88 (13)
Cl2—Co—N1—C13	−51.40 (13)	Cl2—Co—N10—C9	110.85 (12)
N4—Co—N1—C2	4.88 (12)	N4—Co—N10—C11	67.26 (13)
N10—Co—N1—C2	102.18 (12)	N7—Co—N10—C11	150.54 (13)
N7—Co—N1—C2	47.5 (3)	N1—Co—N10—C11	−16.34 (12)
Cl1—Co—N1—C2	−85.23 (11)	C9—N10—C11—C12	172.67 (15)
Cl2—Co—N1—C2	−173.15 (11)	Co—N10—C11—C12	42.28 (16)
C12—N1—C2—C3	136.45 (16)	C13—N1—C12—C11	163.58 (16)
C13—N1—C2—C3	−100.76 (18)	C2—N1—C12—C11	−74.64 (18)
Co—N1—C2—C3	22.33 (18)	Co—N1—C12—C11	41.19 (17)
N1—C2—C3—N4	−47.4 (2)	N10—C11—C12—N1	−54.65 (19)
C2—C3—N4—C5	173.78 (16)	C12—N1—C13—C14	43.5 (2)
C2—C3—N4—Co	51.52 (17)	C2—N1—C13—C14	−77.5 (2)
N10—Co—N4—C3	−116.16 (13)	Co—N1—C13—C14	161.90 (15)
N7—Co—N4—C3	159.17 (13)	N1—C13—C14—C15	−98.0 (2)
N1—Co—N4—C3	−31.72 (12)	N1—C13—C14—C19	87.6 (2)
Cl1—Co—N4—C3	66.29 (12)	C19—C14—C15—C16	1.2 (3)
N10—Co—N4—C5	117.90 (13)	C13—C14—C15—C16	−173.4 (2)
N7—Co—N4—C5	33.23 (13)	C14—C15—C16—C17	−0.9 (4)
N1—Co—N4—C5	−157.66 (14)	C15—C16—C17—C18	−0.3 (4)
Cl1—Co—N4—C5	−59.66 (13)	C15—C16—C17—C20	176.5 (2)
C3—N4—C5—C6	−171.19 (16)	C16—C17—C18—C19	1.1 (4)
Co—N4—C5—C6	−49.04 (18)	C20—C17—C18—C19	−175.8 (2)
N4—C5—C6—N7	40.9 (2)	C17—C18—C19—C14	−0.8 (3)
C5—C6—N7—C8	−134.57 (17)	C15—C14—C19—C18	−0.3 (3)
C5—C6—N7—Co	−15.4 (2)	C13—C14—C19—C18	174.08 (19)
N4—Co—N7—C8	111.19 (13)	C16—C17—C20—O21	173.4 (3)
N10—Co—N7—C8	13.90 (13)	C18—C17—C20—O21	−9.8 (4)
N1—Co—N7—C8	68.5 (3)	C16—C17—C20—O22	−8.0 (4)
Cl1—Co—N7—C8	−158.21 (12)	C18—C17—C20—O22	168.8 (2)
Cl2—Co—N7—C8	−71.12 (12)	O21—C20—O22—C23	−0.5 (5)
N4—Co—N7—C6	−9.53 (13)	C17—C20—O22—C23	−179.1 (3)
N10—Co—N7—C6	−106.82 (13)	O1—S—O4—C4A	48.05 (18)
N1—Co—N7—C6	−52.2 (3)	O2—S—O4—C4A	170.09 (16)
Cl1—Co—N7—C6	81.08 (13)	O3—S—O4—C4A	−71.60 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O3^i	0.88 (3)	1.97 (2)	2.836 (2)	166 (2)
N10—H10···O2	0.81 (2)	2.49 (3)	3.111 (2)	134 (2)
N7—H7···Cl2^ii	0.86 (3)	2.59 (3)	3.3687 (17)	151 (2)

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z.