Bis(2-aminona­phthalene-1-sulfonato-κO)bis­(1,10-phenanthroline-κ²N,N′)cobalt(II)

The title mol­ecule, [Co(C₁₀H₈NO₃S)₂(C₁₂H₁₀N₂)₂], lies on a crystallographic twofold axis with the Co^II atom coordinated by four N atoms from two chelating 1,10-phenanthroline ligands and two sulfonate O atoms from two 2-aminonaph­thalene-1-sulfonate ligands in a distorted octa­hedral geometry. In the crystal structure, inter­molecular C—H...O and N—H...O hydrogen bonds link the mononuclear units into a three-dimensional network. There is also a single N—H...O hydrogen bond and an intra­molecular π–π stacking inter­action.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.024
• wR factor = 0.063
• Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.65 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C15    -   C16     ..       6.12 su
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.11 Ratio

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.03
           From the CIF: _reflns_number_total               3363
           Count of symmetry unique reflns         1999
           Completeness (_total/calc)            168.23%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1364
           Fraction of Friedel pairs measured     0.682
           Are heavy atom types Z>Si present        yes

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

   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX-II (Bruker, 2003); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001) and DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: SHELXTL.

Bis(2-aminonaphthalene-1-sulfonato-κO)bis(1,10-phenanthroline- κ²N,N')cobalt(II)

Crystal data

[Co(C10H8NO3S)2(C12H8N2)2]	Dx = 1.506 Mg m^−3
Mr = 863.81	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41212	Cell parameters from 7533 reflections
Hall symbol: P 4abw 2nw	θ = 2.3–24.6°
a = 12.468 (3) Å	µ = 0.62 mm^−1
c = 24.510 (9) Å	T = 294 K
V = 3810.3 (19) Å^3	Block, red
Z = 4	0.44 × 0.28 × 0.20 mm
F(000) = 1780

Data collection

Bruker APEX-II CCD diffractometer	3363 independent reflections
Radiation source: fine-focus sealed tube	3105 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.812, Tmax = 0.883	k = −14→14
20658 measured reflections	l = −26→29

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)] = 0.024	H-atom parameters constrained
wR(F^2) = 0.063	w = 1/[σ^2(Fo^2) + (0.0406P)^2 + 0.043P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
3363 reflections	Δρmax = 0.13 e Å^−3
267 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Absolute structure: Flack (1983), 1364 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.034 (12)

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
Co1	0.469261 (19)	0.469261 (19)	0.0000	0.03017 (10)
S1	0.46833 (4)	0.21052 (4)	0.035261 (19)	0.03342 (12)
O1	0.44719 (11)	0.32546 (10)	0.04082 (6)	0.0400 (3)
O2	0.42869 (14)	0.16862 (15)	−0.01570 (6)	0.0597 (5)
O3	0.42893 (12)	0.15333 (12)	0.08210 (6)	0.0492 (4)
N2	0.63697 (12)	0.47845 (13)	0.02026 (7)	0.0342 (4)
N3	0.6207 (2)	0.11378 (18)	−0.05275 (8)	0.0716 (7)
H3A	0.5523	0.1168	−0.0569	0.086*
H3B	0.6602	0.0862	−0.0779	0.086*
C1	0.65446 (15)	0.40381 (14)	−0.06907 (8)	0.0325 (4)
C2	0.70287 (15)	0.44332 (14)	−0.02023 (8)	0.0337 (4)
C3	0.68130 (18)	0.51514 (17)	0.06520 (9)	0.0459 (5)
H3	0.6368	0.5392	0.0931	0.055*
C4	0.7929 (2)	0.51965 (19)	0.07296 (11)	0.0587 (7)
H4	0.8212	0.5464	0.1053	0.070*
C5	0.85873 (18)	0.48465 (19)	0.03278 (11)	0.0566 (6)
H5	0.9327	0.4870	0.0375	0.068*
C6	0.81532 (16)	0.44512 (16)	−0.01555 (10)	0.0454 (6)
C7	0.87890 (19)	0.4069 (2)	−0.06113 (12)	0.0571 (7)
H7	0.9533	0.4081	−0.0586	0.068*
C8	0.8326 (2)	0.3702 (2)	−0.10664 (12)	0.0566 (6)
H8	0.8756	0.3462	−0.1351	0.068*
C9	0.71912 (18)	0.36688 (16)	−0.11252 (9)	0.0429 (5)
C13	0.61074 (16)	0.19855 (15)	0.03654 (8)	0.0353 (5)
C14	0.66643 (19)	0.15251 (16)	−0.00648 (10)	0.0478 (6)
C15	0.7798 (2)	0.1446 (2)	−0.00186 (13)	0.0669 (7)
H15	0.8186	0.1131	−0.0300	0.080*
C16	0.8326 (2)	0.1817 (2)	0.04230 (14)	0.0710 (8)
H16	0.9067	0.1742	0.0439	0.085*
C17	0.77856 (19)	0.2317 (2)	0.08652 (10)	0.0540 (6)
C18	0.8331 (2)	0.2728 (3)	0.13259 (15)	0.0760 (9)
H18	0.9075	0.2682	0.1338	0.091*
C19	0.7812 (3)	0.3180 (3)	0.17437 (13)	0.0865 (10)
H19	0.8190	0.3443	0.2042	0.104*
C20	0.6697 (3)	0.3252 (3)	0.17275 (10)	0.0732 (8)
H20	0.6331	0.3561	0.2018	0.088*
C21	0.61329 (19)	0.28723 (19)	0.12878 (8)	0.0486 (6)
H21	0.5390	0.2937	0.1286	0.058*
C22	0.66493 (17)	0.23856 (16)	0.08372 (9)	0.0376 (5)
N1	0.54554 (13)	0.40490 (12)	−0.07163 (6)	0.0343 (4)
C10	0.6663 (2)	0.32863 (18)	−0.15931 (9)	0.0547 (6)
H10	0.7056	0.3030	−0.1888	0.066*
C11	0.5574 (2)	0.32935 (19)	−0.16109 (10)	0.0551 (6)
H11	0.5215	0.3046	−0.1919	0.066*
C12	0.49986 (18)	0.36743 (17)	−0.11641 (9)	0.0453 (6)
H12	0.4254	0.3665	−0.1182	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.02651 (12)	0.02651 (12)	0.0375 (2)	0.00119 (14)	0.00369 (11)	−0.00369 (11)
S1	0.0393 (3)	0.0296 (2)	0.0313 (3)	−0.0023 (2)	−0.0010 (2)	0.0003 (2)
O1	0.0405 (8)	0.0321 (7)	0.0473 (8)	0.0058 (6)	−0.0019 (7)	0.0033 (6)
O2	0.0668 (11)	0.0641 (11)	0.0483 (10)	−0.0055 (8)	−0.0151 (8)	−0.0153 (8)
O3	0.0519 (9)	0.0453 (9)	0.0504 (9)	−0.0057 (7)	0.0104 (7)	0.0130 (7)
N2	0.0305 (8)	0.0279 (8)	0.0441 (10)	−0.0010 (7)	−0.0009 (7)	−0.0022 (8)
N3	0.0925 (18)	0.0678 (15)	0.0544 (13)	−0.0074 (12)	0.0309 (13)	−0.0241 (12)
C1	0.0353 (11)	0.0233 (9)	0.0390 (11)	0.0023 (7)	0.0098 (9)	0.0023 (9)
C2	0.0286 (9)	0.0238 (9)	0.0488 (12)	0.0016 (7)	0.0067 (9)	0.0034 (8)
C3	0.0493 (12)	0.0394 (12)	0.0492 (13)	0.0003 (10)	−0.0046 (11)	−0.0121 (11)
C4	0.0545 (14)	0.0477 (13)	0.0740 (17)	−0.0062 (12)	−0.0252 (13)	−0.0072 (13)
C5	0.0323 (11)	0.0483 (14)	0.0891 (19)	−0.0017 (10)	−0.0137 (13)	0.0009 (14)
C6	0.0291 (10)	0.0352 (11)	0.0720 (16)	−0.0012 (8)	0.0041 (11)	0.0123 (11)
C7	0.0289 (12)	0.0537 (15)	0.089 (2)	0.0065 (10)	0.0184 (13)	0.0119 (15)
C8	0.0482 (14)	0.0540 (15)	0.0677 (16)	0.0101 (12)	0.0324 (13)	0.0067 (13)
C9	0.0467 (13)	0.0317 (11)	0.0502 (13)	0.0058 (9)	0.0182 (11)	0.0056 (10)
C13	0.0404 (11)	0.0280 (10)	0.0374 (12)	0.0056 (8)	0.0085 (9)	0.0065 (9)
C14	0.0601 (14)	0.0318 (10)	0.0516 (14)	0.0018 (10)	0.0215 (12)	−0.0002 (11)
C15	0.0607 (16)	0.0565 (15)	0.083 (2)	0.0115 (12)	0.0354 (17)	0.0000 (16)
C16	0.0382 (13)	0.0643 (17)	0.111 (2)	0.0140 (12)	0.0197 (15)	0.0228 (17)
C17	0.0420 (13)	0.0545 (14)	0.0655 (15)	0.0044 (10)	−0.0040 (13)	0.0244 (13)
C18	0.0460 (15)	0.087 (2)	0.096 (2)	−0.0049 (14)	−0.0296 (16)	0.033 (2)
C19	0.084 (2)	0.110 (3)	0.065 (2)	−0.013 (2)	−0.0405 (19)	0.0074 (19)
C20	0.080 (2)	0.098 (2)	0.0413 (14)	−0.0068 (16)	−0.0180 (14)	−0.0042 (15)
C21	0.0491 (13)	0.0605 (15)	0.0363 (13)	0.0010 (11)	−0.0068 (10)	0.0046 (11)
C22	0.0369 (11)	0.0370 (11)	0.0390 (12)	0.0035 (9)	−0.0016 (9)	0.0136 (9)
N1	0.0335 (9)	0.0308 (8)	0.0386 (9)	0.0008 (7)	0.0056 (8)	−0.0044 (7)
C10	0.082 (2)	0.0405 (13)	0.0417 (13)	0.0094 (12)	0.0197 (13)	−0.0052 (11)
C11	0.0734 (19)	0.0483 (13)	0.0436 (13)	0.0019 (12)	0.0002 (13)	−0.0111 (11)
C12	0.0478 (14)	0.0425 (12)	0.0455 (13)	−0.0011 (10)	−0.0037 (10)	−0.0077 (10)

Geometric parameters (Å, º)

Co1—O1^i	2.0716 (14)	C6—C7	1.450 (3)
Co1—O1	2.0716 (14)	C7—C8	1.337 (4)
Co1—O1	2.0716 (14)	C7—H7	0.9300
Co1—N1^i	2.1520 (16)	C8—C9	1.423 (3)
Co1—N1	2.1520 (16)	C8—H8	0.9300
Co1—N2	2.1523 (16)	C9—C10	1.406 (3)
Co1—N2^i	2.1523 (16)	C13—C14	1.387 (3)
S1—O3	1.4380 (15)	C13—C22	1.429 (3)
S1—O3	1.4380 (15)	C14—C15	1.422 (4)
S1—O2	1.4414 (16)	C15—C16	1.348 (4)
S1—O2	1.4414 (16)	C15—H15	0.9300
S1—O1	1.4635 (14)	C16—C17	1.421 (4)
S1—O1	1.4635 (14)	C16—H16	0.9300
S1—C13	1.782 (2)	C17—C18	1.414 (4)
N2—C3	1.314 (3)	C17—C22	1.421 (3)
N2—C2	1.361 (2)	C18—C19	1.336 (4)
N3—C14	1.358 (3)	C18—H18	0.9300
N3—H3A	0.8600	C19—C20	1.394 (4)
N3—H3B	0.8600	C19—H19	0.9300
C1—N1	1.360 (2)	C20—C21	1.371 (3)
C1—C9	1.413 (3)	C20—H20	0.9300
C1—C2	1.428 (3)	C21—C22	1.415 (3)
C2—C6	1.407 (3)	C21—H21	0.9300
C3—C4	1.405 (3)	N1—C12	1.322 (3)
C3—H3	0.9300	C10—C11	1.359 (4)
C4—C5	1.354 (3)	C10—H10	0.9300
C4—H4	0.9300	C11—C12	1.393 (3)
C5—C6	1.393 (3)	C11—H11	0.9300
C5—H5	0.9300	C12—H12	0.9300
O1^i—Co1—O1	90.19 (8)	C4—C5—C6	119.8 (2)
O1^i—Co1—O1	90.19 (8)	C4—C5—H5	120.1
O1^i—Co1—N1^i	97.47 (6)	C6—C5—H5	120.1
O1—Co1—N1^i	86.50 (6)	C5—C6—C2	117.5 (2)
O1—Co1—N1^i	86.50 (6)	C5—C6—C7	124.0 (2)
O1^i—Co1—N1	86.50 (6)	C2—C6—C7	118.5 (2)
O1—Co1—N1	97.47 (6)	C8—C7—C6	121.3 (2)
O1—Co1—N1	97.47 (6)	C8—C7—H7	119.4
N1^i—Co1—N1	174.40 (9)	C6—C7—H7	119.4
O1^i—Co1—N2	163.61 (6)	C7—C8—C9	121.6 (2)
O1—Co1—N2	93.65 (6)	C7—C8—H8	119.2
O1—Co1—N2	93.65 (6)	C9—C8—H8	119.2
N1^i—Co1—N2	98.66 (6)	C10—C9—C1	117.3 (2)
N1—Co1—N2	77.21 (6)	C10—C9—C8	123.9 (2)
O1^i—Co1—N2^i	93.65 (6)	C1—C9—C8	118.8 (2)
O1—Co1—N2^i	163.61 (6)	C14—C13—C22	121.5 (2)
O1—Co1—N2^i	163.61 (6)	C14—C13—S1	121.34 (18)
N1^i—Co1—N2^i	77.21 (6)	C22—C13—S1	117.13 (15)
N1—Co1—N2^i	98.66 (6)	N3—C14—C13	124.9 (2)
N2—Co1—N2^i	87.12 (8)	N3—C14—C15	117.3 (2)
O3—S1—O2	113.27 (10)	C13—C14—C15	117.8 (3)
O3—S1—O2	113.27 (10)	C16—C15—C14	121.7 (2)
O3—S1—O2	113.27 (10)	C16—C15—H15	119.2
O3—S1—O2	113.27 (10)	C14—C15—H15	119.2
O3—S1—O1	110.47 (9)	C15—C16—C17	122.1 (2)
O3—S1—O1	110.47 (9)	C15—C16—H16	118.9
O2—S1—O1	111.96 (10)	C17—C16—H16	118.9
O2—S1—O1	111.96 (10)	C18—C17—C16	122.7 (3)
O3—S1—O1	110.47 (9)	C18—C17—C22	119.8 (2)
O3—S1—O1	110.47 (9)	C16—C17—C22	117.5 (2)
O2—S1—O1	111.96 (10)	C19—C18—C17	122.1 (3)
O2—S1—O1	111.96 (10)	C19—C18—H18	118.9
O3—S1—C13	106.55 (10)	C17—C18—H18	118.9
O3—S1—C13	106.55 (10)	C18—C19—C20	119.2 (3)
O2—S1—C13	109.06 (10)	C18—C19—H19	120.4
O2—S1—C13	109.06 (10)	C20—C19—H19	120.4
O1—S1—C13	105.06 (9)	C21—C20—C19	120.8 (3)
O1—S1—C13	105.06 (9)	C21—C20—H20	119.6
S1—O1—Co1	141.13 (9)	C19—C20—H20	119.6
C3—N2—C2	117.98 (18)	C20—C21—C22	121.9 (2)
C3—N2—Co1	128.35 (14)	C20—C21—H21	119.1
C2—N2—Co1	113.65 (12)	C22—C21—H21	119.1
C14—N3—H3A	120.0	C21—C22—C17	116.2 (2)
C14—N3—H3B	120.0	C21—C22—C13	124.48 (19)
H3A—N3—H3B	120.0	C17—C22—C13	119.3 (2)
N1—C1—C9	122.58 (19)	C12—N1—C1	117.73 (17)
N1—C1—C2	117.22 (16)	C12—N1—Co1	128.22 (14)
C9—C1—C2	120.19 (18)	C1—N1—Co1	114.05 (13)
N2—C2—C6	122.49 (19)	C11—C10—C9	119.5 (2)
N2—C2—C1	117.84 (17)	C11—C10—H10	120.3
C6—C2—C1	119.67 (18)	C9—C10—H10	120.3
N2—C3—C4	122.9 (2)	C10—C11—C12	119.5 (2)
N2—C3—H3	118.5	C10—C11—H11	120.3
C4—C3—H3	118.5	C12—C11—H11	120.3
C5—C4—C3	119.3 (2)	N1—C12—C11	123.5 (2)
C5—C4—H4	120.4	N1—C12—H12	118.3
C3—C4—H4	120.4	C11—C12—H12	118.3
O3—S1—O1—Co1	179.79 (13)	O1—S1—C13—C14	−121.52 (17)
O3—S1—O1—Co1	179.79 (13)	O1—S1—C13—C14	−121.52 (17)
O2—S1—O1—Co1	−52.98 (17)	O3—S1—C13—C22	−58.85 (17)
O2—S1—O1—Co1	−52.98 (17)	O3—S1—C13—C22	−58.85 (17)
C13—S1—O1—Co1	65.25 (15)	O2—S1—C13—C22	178.56 (15)
O1^i—Co1—O1—S1	88.01 (14)	O2—S1—C13—C22	178.56 (15)
N1^i—Co1—O1—S1	−174.52 (15)	O1—S1—C13—C22	58.39 (17)
N1—Co1—O1—S1	1.52 (15)	O1—S1—C13—C22	58.39 (17)
N2—Co1—O1—S1	−76.05 (15)	C22—C13—C14—N3	−179.3 (2)
N2^i—Co1—O1—S1	−168.28 (16)	S1—C13—C14—N3	0.6 (3)
O1^i—Co1—N2—C3	173.16 (19)	C22—C13—C14—C15	1.0 (3)
O1—Co1—N2—C3	−83.61 (18)	S1—C13—C14—C15	−179.10 (17)
O1—Co1—N2—C3	−83.61 (18)	N3—C14—C15—C16	179.4 (2)
N1^i—Co1—N2—C3	3.40 (18)	C13—C14—C15—C16	−0.9 (4)
N1—Co1—N2—C3	179.55 (18)	C14—C15—C16—C17	−0.7 (4)
N2^i—Co1—N2—C3	80.00 (17)	C15—C16—C17—C18	−178.7 (3)
O1^i—Co1—N2—C2	−5.2 (3)	C15—C16—C17—C22	2.1 (4)
O1—Co1—N2—C2	98.07 (13)	C16—C17—C18—C19	−178.8 (3)
O1—Co1—N2—C2	98.07 (13)	C22—C17—C18—C19	0.4 (4)
N1^i—Co1—N2—C2	−174.92 (13)	C17—C18—C19—C20	0.0 (5)
N1—Co1—N2—C2	1.23 (12)	C18—C19—C20—C21	−0.5 (5)
N2^i—Co1—N2—C2	−98.32 (13)	C19—C20—C21—C22	0.6 (4)
Co1—N2—C2—C6	178.46 (14)	C20—C21—C22—C17	−0.3 (3)
C3—N2—C2—C1	−179.81 (17)	C20—C21—C22—C13	−179.3 (2)
Co1—N2—C2—C1	−1.3 (2)	C18—C17—C22—C21	−0.2 (3)
N1—C1—C2—N2	0.4 (2)	C16—C17—C22—C21	179.0 (2)
C9—C1—C2—N2	179.66 (17)	C18—C17—C22—C13	178.9 (2)
N1—C1—C2—C6	−179.35 (16)	C16—C17—C22—C13	−1.9 (3)
C9—C1—C2—C6	−0.1 (3)	C14—C13—C22—C21	179.4 (2)
C2—N2—C3—C4	0.1 (3)	S1—C13—C22—C21	−0.5 (3)
Co1—N2—C3—C4	−178.14 (17)	C14—C13—C22—C17	0.4 (3)
N2—C3—C4—C5	−0.2 (4)	S1—C13—C22—C17	−179.49 (15)
C3—C4—C5—C6	0.2 (4)	C9—C1—N1—C12	1.5 (3)
C4—C5—C6—C2	−0.1 (3)	C2—C1—N1—C12	−179.28 (17)
C4—C5—C6—C7	179.3 (2)	C9—C1—N1—Co1	−178.54 (14)
N2—C2—C6—C5	0.1 (3)	C2—C1—N1—Co1	0.7 (2)
C1—C2—C6—C5	179.82 (18)	O1^i—Co1—N1—C12	−2.86 (17)
N2—C2—C6—C7	−179.40 (18)	O1—Co1—N1—C12	86.87 (17)
C1—C2—C6—C7	0.4 (3)	O1—Co1—N1—C12	86.87 (17)
C5—C6—C7—C8	−179.8 (2)	N2—Co1—N1—C12	178.94 (18)
C2—C6—C7—C8	−0.3 (3)	N2^i—Co1—N1—C12	−96.03 (17)
C6—C7—C8—C9	0.1 (4)	O1^i—Co1—N1—C1	177.18 (13)
N1—C1—C9—C10	−1.1 (3)	O1—Co1—N1—C1	−93.09 (13)
C2—C1—C9—C10	179.73 (18)	O1—Co1—N1—C1	−93.09 (13)
N1—C1—C9—C8	179.03 (18)	N2—Co1—N1—C1	−1.02 (12)
C2—C1—C9—C8	−0.2 (3)	N2^i—Co1—N1—C1	84.01 (13)
C7—C8—C9—C10	−179.7 (2)	C1—C9—C10—C11	0.5 (3)
C7—C8—C9—C1	0.2 (3)	C8—C9—C10—C11	−179.6 (2)
O3—S1—C13—C14	121.25 (17)	C9—C10—C11—C12	−0.4 (4)
O3—S1—C13—C14	121.25 (17)	C1—N1—C12—C11	−1.4 (3)
O2—S1—C13—C14	−1.3 (2)	Co1—N1—C12—C11	178.67 (16)
O2—S1—C13—C14	−1.3 (2)	C10—C11—C12—N1	0.8 (4)

Symmetry code: (i) y, x, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O3^ii	0.86	2.22	2.901 (3)	137
N3—H3A···O2	0.86	1.95	2.650 (3)	137
C21—H21···O1	0.93	2.47	3.027 (3)	119
C21—H21···O3	0.93	2.50	3.063 (3)	119
C7—H7···O3^iii	0.93	2.57	3.471 (3)	163
C8—H8···O2^iv	0.93	2.53	3.385 (3)	154
C12—H12···O1^i	0.93	2.48	3.025 (3)	117

Symmetry codes: (i) y, x, −z; (ii) y+1/2, −x+1/2, z−1/4; (iii) y+1, x, −z; (iv) x+1/2, −y+1/2, −z−1/4.