Bis(1,10-phenanthroline-κ²N,N′)(sulfato-κ²O,O′)cobalt(II) propane-1,2-diol monosolvate

In the title compound, [Co(SO₄)(C₁₂H₈N₂)₂]·C₃H₈O₂, the Co^II atom (site symmetry 2) has a distorted octa­hedral coordination composed of four N atoms from two chelating 1,10-phenanthroline ligands and two O atoms from an O,O′-bidentate sulfate ligand, in which the S atom has site symmetry 2. The dihedral angle between the two chelating N₂C₂ groups is 84.46 (15)°. The complex and solvent mol­ecules are connected through O—H...O hydrogen bonds. The solvent mol­ecule is equally disordered over two positions and is also located on a twofold axis.

Key indicators

• Single-crystal X-ray study
• T = 223 K
• Mean [sigma](C-C) = 0.008 Å
• Disorder in solvent or counterion
• R factor = 0.052
• wR factor = 0.129
• Data-to-parameter ratio = 11.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW .gt. 10 Outliers .          1

Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         S1
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0077 Ang
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.831
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          3
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595          4
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          5
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained Atom Sites ....          4
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF          ?
PLAT007_ALERT_5_G Note: Number of Unrefined D-H Atoms ............          2
PLAT302_ALERT_4_G Note: Anion/Solvent Disorder ...................        100 Perc.
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         38

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   7 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

---

S1. Comment

In the past few decades, the supramolecular assembly and crystal engineering of metal-organic coordination frameworks have attracted much attention because of their potential applications in the areas of material chemistry (Batten & Robson, 1998; Robin & Fromm, 2006). Recently, we have unexpectedly obtained some cobalt-phen complexes with interesting four-membered chelating rings during attempts to synthesize mixed-ligand coordination polymers with phen as auxiliary ligand via a alcohol-solvothermal reaction, e.g. [CoSO₄(C₁₂H₈N₂)₂]. C₂H₆O₂ (Zhong et al., 2006), (II), [CoSO₄(C₁₂H₈N₂)₂].HOCH₂ CH₂CH₂OH (Zhong, 2010), (III) and [CoSO₄(C₁₂H₈N₂)₂]. C₄H₁₀O₂ (Wang & Zhong, 2011), (IV). The crystal structure of the title compound [CuSO₄(C₁₂H₈N₂)₂].C₃H₈O₂, (I) has hitherto not been reported.

Single-crystal X-ray diffraction revealed that the asymmetric unit of (I) contains one neutral monomeric complex [CuSO₄(C₁₂H₈N₂)₂] and one solvent propane-1,2-diol molecule, which are connected by an intermolecular O—H···O hydrogen bond with the uncoordinated O atoms of the sulfate group (Fig. 1 & Table 2). In the complex, a twofold rotation axis (symmetry code: 0, y, 1/4) passes through the Co^II atom and the S atom. The Co^II atom has a distorted CoN₄O₂ octahedral geometry, with four N atoms from two chelating phenanthroline ligands and two O atoms from an O,O'-bidentate sulfate anion (Fig. 1). The Co—O bond distance [2.124 (3) Å], the Co—N bond distance [2.123 (3) Å], the N—Co—N bite angles [77.50 (13)°] and O—Co—O bite angle [66.91 (16)°] are within normal ranges and are comparable to the closely related structure (II) - (IV). The two chelating N₂C₂ groups are oriented at 84.46 (15)°, which is much larger than reported in (II), (III) and (IV) [70.16 (6)°, 80.06 (8)° and 83.48 (1)°, respectively]. The solvent molecule is disordered over two sets of sites with occupancies of 0.50 and 0.50.

Related literature

The title complex has been reported with other solvant molecules. In the case of ethane-1,2-diol, see: Zhong et al. (2006); for propane-1,3-diol, see: Zhong (2010); for butane-2,3-diol, see: Wang & Zhong (2011). For crystal engineering aspects of coordination framework structures, see: Batten & Robson (1998); Robin & Fromm (2006).

S2. Experimental

0.2 mmol phen, 0.1 mmol melamine, 0.1 mmol CoSO₄.7H₂O, 2.0 ml propane-1,2-diol and 1.0 ml water were mixed and placed in a thick Pyrex tube, which was sealed and heated to 453 K for 96 h, whereupon red block-shaped crystals of the title compound were obtained.

S3. Refinement

All non-hydrogen atoms were refined anisotropically. The H atoms of phen were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C). The H atoms of propane-1,2-diol were placed in geometrically idealized positions and refined as riding atoms, with C—H(CH₃) = 0.96 Å, C—H(CH₂) = 0.97 Å, C—H(CH) = 0.98 Å and O—H = 0.82 Å; U_iso(H) = 1.2U_eq(C) and 1.5U_eq(O). The propane-1,2-diol molecule was found to be disordered over two positions with site occupancy factors of 0.50:0.50. The site occupancy factors were not refined. In order to keep a reasonable geometry distance restraints were used, apart from atomic displacement parameter restraints (ISOR and EADP).

Computing details

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

Fig. 1. The molecular structure showing the atom-numbering scheme and with displacement ellipsoids drawn at the 30% probability level. Hydrogen bonds O—H···O are shown as dashed lines.

Bis(1,10-phenanthroline-κ²N,N')(sulfato- κ²O,O')cobalt(II) propane-1,2-diol monosolvate

Crystal data

[Co(SO4)(C12H8N2)2]·C3H8O2	F(000) = 1220
Mr = 591.49	Dx = 1.520 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5104 reflections
a = 18.117 (4) Å	θ = 3.1–25.4°
b = 12.987 (3) Å	µ = 0.80 mm^−1
c = 12.881 (3) Å	T = 223 K
β = 121.46 (3)°	Block, red
V = 2585.2 (13) Å^3	0.35 × 0.34 × 0.25 mm
Z = 4

Data collection

Rigaku Mercury CCD diffractometer	2284 independent reflections
Radiation source: fine-focus sealed tube	1465 reflections with I > 2/s(I)
Graphite Monochromator monochromator	Rint = 0.100
Detector resolution: 28.5714 pixels mm^-1	θmax = 25.0°, θmin = 3.1°
ω scans	h = −20→21
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −14→15
Tmin = 0.373, Tmax = 1.000	l = −15→15
11477 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.129	w = 1/[σ^2(Fo^2) + (0.0385P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max = 0.001
2284 reflections	Δρmax = 0.37 e Å^−3
193 parameters	Δρmin = −0.39 e Å^−3
38 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0060 (5)

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	Occ. (<1)
Co1	0.0000	0.32137 (6)	0.2500	0.0348 (3)
S1	0.0000	0.52899 (11)	0.2500	0.0344 (4)
O1	0.0533 (2)	0.4578 (2)	0.3537 (3)	0.0495 (9)
O2	−0.0552 (2)	0.5929 (2)	0.2742 (3)	0.0604 (10)
O3	−0.0492 (7)	0.7963 (6)	0.3204 (8)	0.071 (3)	0.50
H3	−0.0428	0.7424	0.2931	0.106*	0.50
O3'	−0.0869 (6)	0.7996 (6)	0.2438 (10)	0.097 (4)	0.50
H3'	−0.0613	0.7472	0.2804	0.145*	0.50
N1	0.0830 (2)	0.3000 (3)	0.1814 (3)	0.0379 (9)
N2	0.0959 (2)	0.2178 (2)	0.3803 (3)	0.0363 (9)
C1	0.0774 (3)	0.3442 (4)	0.0841 (4)	0.0459 (12)
H1A	0.0340	0.3924	0.0406	0.055*
C2	0.1339 (3)	0.3208 (4)	0.0454 (5)	0.0537 (14)
H2A	0.1284	0.3535	−0.0225	0.064*
C3	0.1977 (3)	0.2495 (4)	0.1074 (5)	0.0555 (14)
H3A	0.2354	0.2331	0.0814	0.067*
C4	0.2061 (3)	0.2012 (3)	0.2104 (4)	0.0419 (12)
C5	0.2732 (3)	0.1286 (4)	0.2841 (5)	0.0538 (14)
H5A	0.3117	0.1082	0.2608	0.065*
C6	0.2814 (3)	0.0902 (4)	0.3853 (5)	0.0493 (13)
H6A	0.3258	0.0440	0.4320	0.059*
C7	0.2225 (3)	0.1189 (3)	0.4240 (4)	0.0402 (11)
C8	0.2298 (3)	0.0829 (3)	0.5312 (4)	0.0506 (13)
H8A	0.2738	0.0375	0.5816	0.061*
C9	0.1723 (3)	0.1150 (4)	0.5605 (4)	0.0546 (14)
H9A	0.1767	0.0924	0.6320	0.065*
C10	0.1062 (3)	0.1819 (3)	0.4833 (4)	0.0468 (13)
H10A	0.0671	0.2026	0.5053	0.056*
C11	0.1546 (3)	0.1866 (3)	0.3517 (4)	0.0320 (10)
C12	0.1473 (3)	0.2300 (3)	0.2447 (4)	0.0341 (11)
C13	−0.0288 (6)	0.8772 (5)	0.2729 (9)	0.139 (3)	0.50
H13	−0.0837	0.8822	0.1948	0.167*	0.50
C13'	−0.0288 (6)	0.8772 (5)	0.2729 (9)	0.139 (3)	0.50
H13A	0.0069	0.8799	0.3610	0.167*	0.50
H13B	−0.0613	0.9411	0.2467	0.167*	0.50
C14	−0.0305 (12)	0.9804 (8)	0.3222 (18)	0.168 (9)	0.50
H14A	0.0001	1.0290	0.3021	0.252*	0.50
H14B	−0.0032	0.9762	0.4091	0.252*	0.50
H14C	−0.0894	1.0025	0.2872	0.252*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0323 (5)	0.0367 (5)	0.0407 (6)	0.000	0.0228 (5)	0.000
S1	0.0282 (9)	0.0352 (9)	0.0424 (10)	0.000	0.0203 (8)	0.000
O1	0.048 (2)	0.0428 (18)	0.038 (2)	−0.0012 (15)	0.0091 (17)	0.0020 (15)
O2	0.060 (2)	0.049 (2)	0.095 (3)	0.0103 (17)	0.056 (2)	−0.0082 (19)
O3	0.111 (7)	0.050 (5)	0.077 (6)	0.005 (4)	0.068 (5)	−0.001 (4)
O3'	0.110 (7)	0.067 (6)	0.126 (8)	0.026 (5)	0.070 (6)	0.023 (6)
N1	0.038 (2)	0.042 (2)	0.041 (2)	0.0010 (17)	0.026 (2)	0.0036 (18)
N2	0.041 (2)	0.036 (2)	0.042 (2)	−0.0010 (17)	0.029 (2)	0.0011 (17)
C1	0.041 (3)	0.056 (3)	0.044 (3)	0.003 (2)	0.024 (3)	0.007 (2)
C2	0.054 (3)	0.070 (4)	0.046 (3)	0.003 (3)	0.033 (3)	0.008 (3)
C3	0.050 (3)	0.080 (4)	0.052 (3)	0.004 (3)	0.038 (3)	−0.003 (3)
C4	0.036 (3)	0.057 (3)	0.036 (3)	0.004 (2)	0.021 (2)	−0.002 (2)
C5	0.044 (3)	0.073 (4)	0.050 (3)	0.018 (3)	0.028 (3)	−0.001 (3)
C6	0.037 (3)	0.059 (3)	0.047 (3)	0.015 (2)	0.018 (3)	0.001 (3)
C7	0.036 (3)	0.042 (3)	0.038 (3)	0.005 (2)	0.017 (2)	0.002 (2)
C8	0.046 (3)	0.049 (3)	0.047 (3)	0.007 (2)	0.018 (3)	0.006 (2)
C9	0.063 (4)	0.059 (3)	0.046 (3)	0.005 (3)	0.031 (3)	0.015 (3)
C10	0.056 (3)	0.050 (3)	0.049 (3)	0.003 (2)	0.038 (3)	0.005 (2)
C11	0.033 (3)	0.031 (2)	0.034 (3)	−0.0038 (19)	0.019 (2)	−0.0020 (19)
C12	0.027 (3)	0.041 (3)	0.034 (3)	−0.001 (2)	0.015 (2)	−0.002 (2)
C13	0.195 (9)	0.076 (5)	0.215 (9)	0.002 (5)	0.155 (7)	−0.006 (6)
C13'	0.195 (9)	0.076 (5)	0.215 (9)	0.002 (5)	0.155 (7)	−0.006 (6)
C14	0.20 (2)	0.069 (10)	0.32 (3)	−0.029 (11)	0.19 (2)	−0.032 (14)

Geometric parameters (Å, º)

Co1—O1	2.124 (3)	C3—C4	1.402 (6)
Co1—O1^i	2.124 (3)	C3—H3A	0.9300
Co1—N1	2.123 (3)	C4—C12	1.400 (6)
Co1—N1^i	2.123 (3)	C4—C5	1.437 (6)
Co1—N2^i	2.145 (4)	C5—C6	1.330 (6)
Co1—N2	2.145 (4)	C5—H5A	0.9300
Co1—S1	2.6964 (18)	C6—C7	1.442 (6)
S1—O2^i	1.453 (3)	C6—H6A	0.9300
S1—O2	1.453 (3)	C7—C11	1.399 (6)
S1—O1^i	1.492 (3)	C7—C8	1.397 (6)
S1—O1	1.492 (3)	C8—C9	1.346 (6)
O3—C13	1.361 (4)	C8—H8A	0.9300
O3—H3	0.8200	C9—C10	1.391 (6)
O3'—H3'	0.8200	C9—H9A	0.9300
N1—C1	1.333 (5)	C10—H10A	0.9300
N1—C12	1.363 (5)	C11—C12	1.430 (6)
N2—C10	1.324 (5)	C13—C13^i	1.443 (7)
N2—C11	1.356 (5)	C13—C14	1.489 (9)
C1—C2	1.386 (6)	C13—H13	0.9800
C1—H1A	0.9300	C14—H14A	0.9600
C2—C3	1.366 (6)	C14—H14B	0.9600
C2—H2A	0.9300	C14—H14C	0.9600
O1—Co1—O1^i	66.91 (16)	C1—C2—H2A	120.2
O1—Co1—N1	100.51 (13)	C2—C3—C4	119.9 (4)
O1^i—Co1—N1	92.02 (13)	C2—C3—H3A	120.1
O1—Co1—N1^i	92.02 (13)	C4—C3—H3A	120.1
O1^i—Co1—N1^i	100.51 (13)	C12—C4—C3	117.0 (4)
N1—Co1—N1^i	165.01 (18)	C12—C4—C5	119.2 (4)
O1—Co1—N2^i	158.77 (12)	C3—C4—C5	123.8 (4)
O1^i—Co1—N2^i	96.57 (12)	C6—C5—C4	121.1 (4)
N1—Co1—N2^i	93.03 (13)	C6—C5—H5A	119.5
N1^i—Co1—N2^i	77.50 (13)	C4—C5—H5A	119.5
O1—Co1—N2	96.57 (12)	C5—C6—C7	121.2 (4)
O1^i—Co1—N2	158.77 (12)	C5—C6—H6A	119.4
N1—Co1—N2	77.50 (13)	C7—C6—H6A	119.4
N1^i—Co1—N2	93.03 (13)	C11—C7—C8	117.7 (4)
N2^i—Co1—N2	102.31 (18)	C11—C7—C6	119.0 (4)
O1—Co1—S1	33.45 (8)	C8—C7—C6	123.3 (4)
O1^i—Co1—S1	33.45 (8)	C9—C8—C7	119.0 (4)
N1—Co1—S1	97.50 (9)	C9—C8—H8A	120.5
N1^i—Co1—S1	97.50 (9)	C7—C8—H8A	120.5
N2^i—Co1—S1	128.85 (9)	C8—C9—C10	119.7 (5)
N2—Co1—S1	128.85 (9)	C8—C9—H9A	120.1
O2^i—S1—O2	110.3 (3)	C10—C9—H9A	120.1
O2^i—S1—O1^i	111.01 (19)	N2—C10—C9	123.8 (4)
O2—S1—O1^i	110.46 (19)	N2—C10—H10A	118.1
O2^i—S1—O1	110.46 (19)	C9—C10—H10A	118.1
O2—S1—O1	111.01 (19)	N2—C11—C7	123.3 (4)
O1^i—S1—O1	103.4 (2)	N2—C11—C12	116.9 (4)
O2^i—S1—Co1	124.83 (13)	C7—C11—C12	119.7 (4)
O2—S1—Co1	124.83 (13)	N1—C12—C4	122.9 (4)
O1^i—S1—Co1	51.70 (12)	N1—C12—C11	117.4 (4)
O1—S1—Co1	51.70 (12)	C4—C12—C11	119.8 (4)
S1—O1—Co1	94.85 (16)	O3—C13—C13^i	127.5 (5)
C13—O3—H3	109.5	O3—C13—C14	115.6 (8)
C1—N1—C12	118.1 (4)	C13^i—C13—C14	110.8 (7)
C1—N1—Co1	127.8 (3)	O3—C13—H13	98.3
C12—N1—Co1	114.1 (3)	C13^i—C13—H13	98.3
C10—N2—C11	116.5 (4)	C14—C13—H13	98.3
C10—N2—Co1	129.7 (3)	C13—C14—H14A	109.5
C11—N2—Co1	113.9 (3)	C13—C14—H14B	109.5
N1—C1—C2	122.4 (4)	H14A—C14—H14B	109.5
N1—C1—H1A	118.8	C13—C14—H14C	109.5
C2—C1—H1A	118.8	H14A—C14—H14C	109.5
C3—C2—C1	119.7 (5)	H14B—C14—H14C	109.5
C3—C2—H2A	120.2
O1—Co1—S1—O2^i	89.6 (2)	N2^i—Co1—N2—C10	−94.6 (4)
O1^i—Co1—S1—O2^i	−90.4 (2)	S1—Co1—N2—C10	85.4 (4)
N1—Co1—S1—O2^i	−8.1 (2)	O1—Co1—N2—C11	−103.3 (3)
N1^i—Co1—S1—O2^i	171.9 (2)	O1^i—Co1—N2—C11	−65.9 (5)
N2^i—Co1—S1—O2^i	−108.2 (2)	N1—Co1—N2—C11	−4.0 (3)
N2—Co1—S1—O2^i	71.8 (2)	N1^i—Co1—N2—C11	164.3 (3)
O1—Co1—S1—O2	−90.4 (2)	N2^i—Co1—N2—C11	86.4 (3)
O1^i—Co1—S1—O2	89.6 (2)	S1—Co1—N2—C11	−93.6 (3)
N1—Co1—S1—O2	171.9 (2)	C12—N1—C1—C2	0.4 (7)
N1^i—Co1—S1—O2	−8.1 (2)	Co1—N1—C1—C2	−177.4 (3)
N2^i—Co1—S1—O2	71.8 (2)	N1—C1—C2—C3	0.5 (8)
N2—Co1—S1—O2	−108.2 (2)	C1—C2—C3—C4	−0.6 (8)
O1—Co1—S1—O1^i	180.0	C2—C3—C4—C12	−0.3 (7)
N1—Co1—S1—O1^i	82.27 (19)	C2—C3—C4—C5	−177.3 (5)
N1^i—Co1—S1—O1^i	−97.73 (19)	C12—C4—C5—C6	−1.3 (7)
N2^i—Co1—S1—O1^i	−17.8 (2)	C3—C4—C5—C6	175.6 (5)
N2—Co1—S1—O1^i	162.2 (2)	C4—C5—C6—C7	0.8 (8)
O1^i—Co1—S1—O1	180.0	C5—C6—C7—C11	1.5 (7)
N1—Co1—S1—O1	−97.73 (19)	C5—C6—C7—C8	−178.2 (5)
N1^i—Co1—S1—O1	82.27 (19)	C11—C7—C8—C9	−0.4 (7)
N2^i—Co1—S1—O1	162.2 (2)	C6—C7—C8—C9	179.2 (4)
N2—Co1—S1—O1	−17.8 (2)	C7—C8—C9—C10	0.8 (7)
O2^i—S1—O1—Co1	−118.82 (17)	C11—N2—C10—C9	−0.6 (7)
O2—S1—O1—Co1	118.44 (18)	Co1—N2—C10—C9	−179.5 (3)
O1^i—S1—O1—Co1	0.0	C8—C9—C10—N2	−0.4 (8)
O1^i—Co1—O1—S1	0.0	C10—N2—C11—C7	1.0 (6)
N1—Co1—O1—S1	87.70 (17)	Co1—N2—C11—C7	−179.9 (3)
N1^i—Co1—O1—S1	−100.56 (16)	C10—N2—C11—C12	−176.1 (4)
N2^i—Co1—O1—S1	−41.1 (4)	Co1—N2—C11—C12	3.0 (5)
N2—Co1—O1—S1	166.15 (15)	C8—C7—C11—N2	−0.6 (7)
O1—Co1—N1—C1	−83.2 (4)	C6—C7—C11—N2	179.8 (4)
O1^i—Co1—N1—C1	−16.3 (4)	C8—C7—C11—C12	176.5 (4)
N1^i—Co1—N1—C1	130.6 (4)	C6—C7—C11—C12	−3.1 (6)
N2^i—Co1—N1—C1	80.4 (4)	C1—N1—C12—C4	−1.4 (6)
N2—Co1—N1—C1	−177.6 (4)	Co1—N1—C12—C4	176.7 (3)
S1—Co1—N1—C1	−49.4 (4)	C1—N1—C12—C11	177.4 (4)
O1—Co1—N1—C12	99.0 (3)	Co1—N1—C12—C11	−4.5 (5)
O1^i—Co1—N1—C12	165.9 (3)	C3—C4—C12—N1	1.3 (7)
N1^i—Co1—N1—C12	−47.3 (3)	C5—C4—C12—N1	178.4 (4)
N2^i—Co1—N1—C12	−97.5 (3)	C3—C4—C12—C11	−177.5 (4)
N2—Co1—N1—C12	4.5 (3)	C5—C4—C12—C11	−0.4 (6)
S1—Co1—N1—C12	132.7 (3)	N2—C11—C12—N1	1.0 (6)
O1—Co1—N2—C10	75.6 (4)	C7—C11—C12—N1	−176.3 (4)
O1^i—Co1—N2—C10	113.1 (5)	N2—C11—C12—C4	179.9 (4)
N1—Co1—N2—C10	175.0 (4)	C7—C11—C12—C4	2.6 (6)
N1^i—Co1—N2—C10	−16.8 (4)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.95	2.698 (9)	150
O3′—H3′···O2	0.82	2.01	2.730 (10)	146