Bis{2-[2-(hydroxy­meth­yl)­phenyl­imino­meth­yl]­phenolato}cobalt(III) nitrate monohydrate

The title compound, [Co(C₁₄H₁₂NO₂)₂]NO₃·H₂O, is the first structurally characterized mononuclear complex of the mono­anionic tridentate N-(2-hydroxy­methyl­phen­yl)­salycylidene­iminate ligand. The Co atom has an octa­hedral environment formed by two ligands with meridional coordination.

Key indicators

• Single-crystal X-ray study
• T = 303 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.036
• wR factor = 0.096
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

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Alert level C
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: CrystalStructure (Rigaku/MSC, 2006); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Version 1.076; Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

Bis{2-[2-(hydroxymethyl)phenyliminomethyl]phenolato}cobalt(III) nitrate monohydrate

Crystal data

[Co(C14H12NO2)2]NO3·H2O	Z = 2
Mr = 591.46	F(000) = 612.00
Triclinic, P1	Dx = 1.503 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 9.5409 (18) Å	Cell parameters from 25 reflections
b = 12.257 (3) Å	θ = 10.2–11.4°
c = 13.477 (4) Å	µ = 0.71 mm^−1
α = 115.68 (2)°	T = 303 K
β = 97.30 (2)°	Prism, dark brown
γ = 106.18 (2)°	0.50 × 0.50 × 0.40 mm
V = 1307.0 (7) Å^3

Data collection

Rigaku AFC-5S diffractometer	Rint = 0.023
ω–2θ scans	θmax = 27.5°
Absorption correction: ψ scan (North et al., 1968)	h = −12→11
Tmin = 0.716, Tmax = 0.751	k = 0→15
6286 measured reflections	l = −17→15
6009 independent reflections	3 standard reflections every 150 reflections
4269 reflections with I > 2σ(I)	intensity decay: 18.8%

Refinement

Refinement on F^2	w = 1/[σ^2(Fo^2) + (0.04P)^2 + 0.3547P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.036	(Δ/σ)max < 0.001
wR(F^2) = 0.096	Δρmax = 0.37 e Å^−3
S = 1.03	Δρmin = −0.31 e Å^−3
6009 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
379 parameters	Extinction coefficient: 0.0079 (9)
H atoms treated by a mixture of independent and constrained refinement

Special details

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Co1	0.41501 (3)	0.15369 (3)	0.27058 (3)	0.02662 (10)
O1	0.40968 (19)	0.10718 (16)	0.39179 (14)	0.0322 (3)
O2	0.40832 (18)	0.18381 (15)	0.14637 (13)	0.0338 (3)
O3	0.51980 (18)	0.03631 (16)	0.20190 (15)	0.0333 (3)
O4	0.33306 (18)	0.27768 (15)	0.34317 (13)	0.0333 (3)
O5	0.1573 (2)	0.1050 (2)	0.65630 (18)	0.0602 (5)
O6	0.3631 (2)	0.0686 (2)	0.68382 (18)	0.0552 (5)
O7	0.2176 (3)	0.0622 (3)	0.7906 (2)	0.0893 (8)
O8	0.1562 (2)	0.0697 (2)	0.4406 (2)	0.0575 (5)
N1	0.6149 (2)	0.28906 (18)	0.35487 (16)	0.0314 (4)
N2	0.2136 (2)	0.01637 (17)	0.18451 (15)	0.0283 (3)
N3	0.2463 (2)	0.0784 (2)	0.71073 (19)	0.0429 (5)
C1	0.5072 (2)	0.2071 (2)	0.5064 (2)	0.0393 (5)
C2	0.6685 (2)	0.2314 (2)	0.50317 (19)	0.0335 (5)
C3	0.7690 (2)	0.2131 (2)	0.5723 (2)	0.0420 (5)
C4	0.9176 (3)	0.2344 (2)	0.5667 (2)	0.0469 (6)
C5	0.9661 (2)	0.2734 (2)	0.4913 (2)	0.0456 (6)
C6	0.8678 (2)	0.2930 (2)	0.4218 (2)	0.0408 (5)
C7	0.7200 (2)	0.2734 (2)	0.42873 (19)	0.0316 (4)
C8	0.6599 (2)	0.3900 (2)	0.3413 (2)	0.0390 (5)
C9	0.5776 (2)	0.4091 (2)	0.2574 (2)	0.0387 (5)
C10	0.6226 (3)	0.5332 (2)	0.2664 (2)	0.0563 (7)
C11	0.5486 (3)	0.5545 (3)	0.1869 (3)	0.0627 (8)
C12	0.4300 (3)	0.4511 (2)	0.0943 (2)	0.0523 (7)
C13	0.3839 (3)	0.3283 (2)	0.0811 (2)	0.0408 (5)
C14	0.4556 (2)	0.3034 (2)	0.1629 (2)	0.0338 (5)
C15	0.4326 (2)	−0.0799 (2)	0.0933 (2)	0.0366 (5)
C16	0.3011 (2)	−0.1649 (2)	0.10882 (19)	0.0323 (4)
C17	0.2845 (3)	−0.2906 (2)	0.0839 (2)	0.0432 (6)
C18	0.1625 (3)	−0.3684 (2)	0.0979 (2)	0.0484 (6)
C19	0.0541 (3)	−0.3211 (2)	0.1376 (2)	0.0455 (6)
C20	0.0682 (2)	−0.1951 (2)	0.1654 (2)	0.0374 (5)
C21	0.1921 (2)	−0.1168 (2)	0.15179 (18)	0.0294 (4)
C22	0.0967 (2)	0.0427 (2)	0.15892 (19)	0.0321 (4)
C23	0.0959 (2)	0.1713 (2)	0.1952 (2)	0.0329 (4)
C24	−0.0291 (3)	0.1852 (2)	0.1413 (2)	0.0445 (6)
C25	−0.0335 (3)	0.3064 (3)	0.1720 (2)	0.0534 (7)
C26	0.0851 (3)	0.4156 (2)	0.2601 (2)	0.0503 (6)
C27	0.2059 (3)	0.4053 (2)	0.3167 (2)	0.0422 (5)
C28	0.2152 (2)	0.2830 (2)	0.28543 (19)	0.0318 (4)
H1	0.324 (4)	0.090 (3)	0.400 (3)	0.075 (11)*
H2	0.4880	0.1780	0.5615	0.047*
H3	0.4872	0.2867	0.5290	0.047*
H4	0.7366	0.1863	0.6232	0.050*
H5	0.9845	0.2224	0.6140	0.056*
H6	1.0654	0.2866	0.4870	0.055*
H7	0.9007	0.3192	0.3708	0.049*
H8	0.7533	0.4555	0.3898	0.047*
H9	0.7041	0.6020	0.3275	0.068*
H10	0.5778	0.6375	0.1949	0.075*
H11	0.3805	0.4655	0.0398	0.063*
H12	0.3045	0.2605	0.0176	0.049*
H13	0.546 (4)	0.007 (3)	0.242 (3)	0.096 (14)*
H14	0.4971	−0.1273	0.0632	0.044*
H15	0.3954	−0.0557	0.0384	0.044*
H16	0.3573	−0.3232	0.0572	0.052*
H17	0.1531	−0.4528	0.0806	0.058*
H18	−0.0292	−0.3743	0.1458	0.055*
H19	−0.0046	−0.1632	0.1930	0.045*
H20	0.0053	−0.0274	0.1132	0.038*
H21	−0.1100	0.1113	0.0841	0.053*
H22	−0.1148	0.3151	0.1342	0.064*
H23	0.0823	0.4979	0.2812	0.060*
H24	0.2828	0.4802	0.3766	0.051*
H25	0.063 (2)	0.014 (3)	0.395 (2)	0.091 (12)*
H26	0.170 (4)	0.085 (3)	0.5147 (18)	0.088 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.02532 (16)	0.02468 (15)	0.02824 (16)	0.00886 (11)	0.00571 (11)	0.01248 (12)
O1	0.0280 (8)	0.0354 (8)	0.0317 (8)	0.0086 (7)	0.0072 (6)	0.0176 (7)
O2	0.0394 (9)	0.0321 (8)	0.0308 (8)	0.0134 (7)	0.0092 (6)	0.0165 (7)
O3	0.0301 (8)	0.0322 (8)	0.0367 (9)	0.0133 (6)	0.0090 (6)	0.0151 (7)
O4	0.0335 (8)	0.0289 (8)	0.0314 (8)	0.0130 (6)	0.0046 (6)	0.0102 (6)
O5	0.0499 (11)	0.0875 (15)	0.0570 (12)	0.0414 (11)	0.0122 (9)	0.0383 (11)
O6	0.0420 (10)	0.0770 (14)	0.0705 (13)	0.0344 (10)	0.0261 (10)	0.0463 (12)
O7	0.0920 (19)	0.156 (2)	0.0923 (18)	0.0857 (19)	0.0591 (16)	0.089 (2)
O8	0.0371 (11)	0.0808 (15)	0.0560 (13)	0.0164 (10)	0.0180 (10)	0.0369 (12)
N1	0.0292 (9)	0.0301 (9)	0.0320 (10)	0.0091 (7)	0.0045 (7)	0.0153 (8)
N2	0.0280 (9)	0.0260 (9)	0.0273 (9)	0.0105 (7)	0.0063 (7)	0.0104 (7)
N3	0.0361 (11)	0.0467 (12)	0.0421 (12)	0.0184 (9)	0.0087 (9)	0.0174 (10)
C1	0.0382 (13)	0.0434 (14)	0.0275 (11)	0.0100 (11)	0.0066 (10)	0.0140 (10)
C2	0.0320 (12)	0.0309 (11)	0.0299 (11)	0.0080 (9)	0.0013 (9)	0.0129 (9)
C3	0.0441 (14)	0.0412 (13)	0.0357 (13)	0.0125 (11)	0.0021 (11)	0.0193 (11)
C4	0.0412 (14)	0.0469 (15)	0.0452 (15)	0.0177 (12)	−0.0035 (11)	0.0199 (12)
C5	0.0304 (12)	0.0473 (15)	0.0498 (15)	0.0135 (11)	0.0033 (11)	0.0187 (12)
C6	0.0343 (12)	0.0410 (13)	0.0426 (14)	0.0104 (10)	0.0073 (10)	0.0200 (11)
C7	0.0294 (11)	0.0276 (11)	0.0300 (11)	0.0082 (9)	0.0013 (9)	0.0110 (9)
C8	0.0332 (12)	0.0344 (12)	0.0440 (14)	0.0070 (10)	0.0042 (10)	0.0201 (11)
C9	0.0407 (13)	0.0315 (12)	0.0444 (14)	0.0092 (10)	0.0107 (11)	0.0221 (11)
C10	0.0566 (17)	0.0417 (15)	0.0645 (19)	0.0064 (13)	0.0040 (14)	0.0318 (14)
C11	0.074 (2)	0.0447 (16)	0.076 (2)	0.0190 (15)	0.0112 (17)	0.0405 (16)
C12	0.0635 (18)	0.0565 (17)	0.0590 (18)	0.0301 (15)	0.0182 (15)	0.0420 (15)
C13	0.0454 (14)	0.0474 (14)	0.0409 (13)	0.0230 (12)	0.0152 (11)	0.0269 (12)
C14	0.0386 (12)	0.0361 (12)	0.0347 (12)	0.0174 (10)	0.0165 (10)	0.0204 (10)
C15	0.0355 (12)	0.0364 (12)	0.0340 (12)	0.0170 (10)	0.0110 (10)	0.0114 (10)
C16	0.0340 (12)	0.0285 (11)	0.0296 (11)	0.0143 (9)	0.0042 (9)	0.0101 (9)
C17	0.0449 (14)	0.0337 (13)	0.0434 (14)	0.0185 (11)	0.0054 (11)	0.0121 (11)
C18	0.0564 (17)	0.0246 (12)	0.0511 (16)	0.0122 (11)	0.0023 (13)	0.0129 (11)
C19	0.0465 (15)	0.0324 (13)	0.0444 (14)	0.0031 (11)	0.0082 (12)	0.0162 (11)
C20	0.0334 (12)	0.0315 (12)	0.0378 (13)	0.0088 (9)	0.0071 (10)	0.0120 (10)
C21	0.0312 (11)	0.0252 (10)	0.0250 (10)	0.0097 (8)	0.0028 (8)	0.0085 (8)
C22	0.0286 (11)	0.0305 (11)	0.0302 (11)	0.0116 (9)	0.0047 (9)	0.0098 (9)
C23	0.0345 (12)	0.0347 (12)	0.0322 (11)	0.0181 (10)	0.0085 (9)	0.0158 (10)
C24	0.0458 (15)	0.0474 (15)	0.0356 (13)	0.0250 (12)	0.0054 (11)	0.0136 (11)
C25	0.0670 (19)	0.0647 (19)	0.0465 (16)	0.0458 (16)	0.0137 (14)	0.0301 (15)
C26	0.0687 (19)	0.0444 (15)	0.0556 (17)	0.0374 (14)	0.0228 (15)	0.0280 (14)
C27	0.0499 (15)	0.0323 (12)	0.0464 (14)	0.0198 (11)	0.0166 (12)	0.0177 (11)
C28	0.0365 (12)	0.0334 (11)	0.0314 (11)	0.0175 (10)	0.0153 (9)	0.0167 (9)

Geometric parameters (Å, º)

Co1—O1	1.951 (2)	C19—C20	1.383 (4)
Co1—O2	1.861 (2)	C20—C21	1.389 (3)
Co1—O3	1.9516 (19)	C22—C23	1.436 (3)
Co1—O4	1.8564 (18)	C23—C24	1.408 (4)
Co1—N1	1.9322 (15)	C23—C28	1.409 (2)
Co1—N2	1.9519 (14)	C24—C25	1.373 (5)
O1—C1	1.453 (2)	C25—C26	1.385 (3)
O2—C14	1.314 (3)	C26—C27	1.367 (4)
O3—C15	1.445 (2)	C27—C28	1.403 (4)
O4—C28	1.318 (3)	O1—H1	0.82 (3)
O5—N3	1.252 (4)	O3—H13	0.81 (5)
O6—N3	1.235 (3)	O8—H25	0.90 (2)
O7—N3	1.226 (4)	O8—H26	0.92 (2)
N1—C7	1.433 (3)	C1—H2	0.970
N1—C8	1.292 (4)	C1—H3	0.970
N2—C21	1.438 (3)	C3—H4	0.930
N2—C22	1.291 (3)	C4—H5	0.930
C1—C2	1.495 (3)	C5—H6	0.930
C2—C3	1.382 (4)	C6—H7	0.930
C2—C7	1.395 (4)	C8—H8	0.930
C3—C4	1.386 (4)	C10—H9	0.930
C4—C5	1.376 (5)	C11—H10	0.930
C5—C6	1.383 (4)	C12—H11	0.930
C6—C7	1.385 (3)	C13—H12	0.930
C8—C9	1.433 (4)	C15—H14	0.970
C9—C10	1.406 (4)	C15—H15	0.970
C9—C14	1.417 (2)	C17—H16	0.930
C10—C11	1.366 (6)	C18—H17	0.930
C11—C12	1.384 (3)	C19—H18	0.930
C12—C13	1.367 (4)	C20—H19	0.930
C13—C14	1.411 (4)	C22—H20	0.930
C15—C16	1.494 (3)	C24—H21	0.930
C16—C17	1.384 (4)	C25—H22	0.930
C16—C21	1.401 (3)	C26—H23	0.930
C17—C18	1.376 (4)	C27—H24	0.930
C18—C19	1.377 (4)
O1—Co1—O2	175.15 (5)	C22—C23—C24	119.00 (18)
O1—Co1—O3	90.42 (9)	C22—C23—C28	121.5 (2)
O1—Co1—O4	89.95 (8)	C24—C23—C28	119.4 (2)
O1—Co1—N1	92.18 (8)	C23—C24—C25	121.0 (2)
O1—Co1—N2	88.05 (8)	C24—C25—C26	119.0 (3)
O2—Co1—O3	87.86 (9)	C25—C26—C27	121.5 (3)
O2—Co1—O4	92.18 (8)	C26—C27—C28	120.7 (2)
O2—Co1—N1	92.24 (8)	O4—C28—C23	123.1 (2)
O2—Co1—N2	87.52 (8)	O4—C28—C27	118.62 (17)
O3—Co1—O4	174.67 (5)	C23—C28—C27	118.3 (2)
O3—Co1—N1	86.60 (7)	Co1—O1—H1	110 (3)
O3—Co1—N2	93.06 (7)	C1—O1—H1	104 (2)
O4—Co1—N1	88.07 (7)	Co1—O3—H13	113 (3)
O4—Co1—N2	92.26 (7)	C15—O3—H13	103 (2)
N1—Co1—N2	179.60 (8)	H25—O8—H26	113 (3)
Co1—O1—C1	116.69 (17)	O1—C1—H2	110.2
Co1—O2—C14	120.60 (14)	O1—C1—H3	110.2
Co1—O3—C15	116.07 (15)	C2—C1—H2	110.2
Co1—O4—C28	120.86 (12)	C2—C1—H3	110.2
Co1—N1—C7	119.35 (16)	H2—C1—H3	108.5
Co1—N1—C8	121.75 (18)	C2—C3—H4	119.7
C7—N1—C8	118.77 (18)	C4—C3—H4	119.7
Co1—N2—C21	120.01 (15)	C3—C4—H5	120.0
Co1—N2—C22	121.38 (15)	C5—C4—H5	120.0
C21—N2—C22	118.57 (16)	C4—C5—H6	119.8
O5—N3—O6	119.9 (2)	C6—C5—H6	119.8
O5—N3—O7	120.0 (2)	C5—C6—H7	120.2
O6—N3—O7	120.1 (3)	C7—C6—H7	120.2
O1—C1—C2	107.52 (19)	N1—C8—H8	117.4
C1—C2—C3	121.6 (2)	C9—C8—H8	117.4
C1—C2—C7	119.6 (2)	C9—C10—H9	119.4
C3—C2—C7	118.8 (2)	C11—C10—H9	119.4
C2—C3—C4	120.7 (3)	C10—C11—H10	120.3
C3—C4—C5	120.0 (3)	C12—C11—H10	120.4
C4—C5—C6	120.3 (2)	C11—C12—H11	119.2
C5—C6—C7	119.5 (3)	C13—C12—H11	119.2
N1—C7—C2	118.8 (2)	C12—C13—H12	119.7
N1—C7—C6	120.5 (2)	C14—C13—H12	119.7
C2—C7—C6	120.7 (2)	O3—C15—H14	109.7
N1—C8—C9	125.28 (19)	O3—C15—H15	109.7
C8—C9—C10	119.5 (2)	C16—C15—H14	109.7
C8—C9—C14	120.9 (2)	C16—C15—H15	109.7
C10—C9—C14	119.5 (2)	H14—C15—H15	108.2
C9—C10—C11	121.2 (2)	C16—C17—H16	119.3
C10—C11—C12	119.3 (3)	C18—C17—H16	119.3
C11—C12—C13	121.6 (3)	C17—C18—H17	120.1
C12—C13—C14	120.7 (2)	C19—C18—H17	120.1
O2—C14—C9	123.5 (2)	C18—C19—H18	119.7
O2—C14—C13	118.61 (17)	C20—C19—H18	119.7
C9—C14—C13	117.8 (2)	C19—C20—H19	120.3
O3—C15—C16	110.0 (2)	C21—C20—H19	120.3
C15—C16—C17	121.8 (2)	N2—C22—H20	117.3
C15—C16—C21	119.9 (2)	C23—C22—H20	117.3
C17—C16—C21	118.3 (2)	C23—C24—H21	119.5
C16—C17—C18	121.3 (2)	C25—C24—H21	119.5
C17—C18—C19	119.8 (2)	C24—C25—H22	120.5
C18—C19—C20	120.6 (2)	C26—C25—H22	120.5
C19—C20—C21	119.3 (2)	C25—C26—H23	119.3
N2—C21—C16	118.6 (2)	C27—C26—H23	119.2
N2—C21—C20	120.8 (2)	C26—C27—H24	119.6
C16—C21—C20	120.6 (2)	C28—C27—H24	119.6
N2—C22—C23	125.40 (17)
O1—Co1—O3—C15	110.13 (19)	O1—C1—C2—C7	59.5 (3)
O3—Co1—O1—C1	109.69 (17)	C1—C2—C3—C4	179.1 (2)
O1—Co1—O4—C28	−130.71 (19)	C1—C2—C7—N1	−1.6 (2)
O4—Co1—O1—C1	−64.99 (18)	C1—C2—C7—C6	−178.17 (19)
O1—Co1—N1—C7	31.68 (18)	C3—C2—C7—N1	178.39 (18)
O1—Co1—N1—C8	−152.6 (2)	C3—C2—C7—C6	1.8 (3)
N1—Co1—O1—C1	23.08 (18)	C7—C2—C3—C4	−0.9 (3)
O1—Co1—N2—C21	−60.29 (18)	C2—C3—C4—C5	−0.4 (3)
O1—Co1—N2—C22	117.5 (2)	C3—C4—C5—C6	0.8 (3)
N2—Co1—O1—C1	−157.25 (18)	C4—C5—C6—C7	0.1 (2)
O2—Co1—O3—C15	−65.34 (19)	C5—C6—C7—N1	−177.9 (2)
O3—Co1—O2—C14	−129.07 (19)	C5—C6—C7—C2	−1.4 (3)
O2—Co1—O4—C28	44.94 (19)	N1—C8—C9—C10	166.9 (2)
O4—Co1—O2—C14	45.60 (19)	N1—C8—C9—C14	−15.8 (4)
O2—Co1—N1—C7	−146.34 (17)	C8—C9—C10—C11	178.7 (3)
O2—Co1—N1—C8	29.4 (2)	C8—C9—C14—O2	1.1 (4)
N1—Co1—O2—C14	−42.55 (19)	C8—C9—C14—C13	−177.4 (2)
O2—Co1—N2—C21	117.75 (18)	C10—C9—C14—O2	178.4 (2)
O2—Co1—N2—C22	−64.5 (2)	C10—C9—C14—C13	−0.1 (3)
N2—Co1—O2—C14	137.77 (19)	C14—C9—C10—C11	1.4 (5)
O3—Co1—N1—C7	−58.62 (18)	C9—C10—C11—C12	−1.7 (5)
O3—Co1—N1—C8	117.1 (2)	C10—C11—C12—C13	0.7 (5)
N1—Co1—O3—C15	−157.7 (2)	C11—C12—C13—C14	0.7 (5)
O3—Co1—N2—C21	30.03 (19)	C12—C13—C14—O2	−179.5 (2)
O3—Co1—N2—C22	−152.2 (2)	C12—C13—C14—C9	−0.9 (4)
N2—Co1—O3—C15	22.1 (2)	O3—C15—C16—C17	−119.5 (2)
O4—Co1—N1—C7	121.55 (18)	O3—C15—C16—C21	59.2 (3)
O4—Co1—N1—C8	−62.7 (2)	C15—C16—C17—C18	−179.6 (2)
N1—Co1—O4—C28	137.1 (2)	C15—C16—C21—N2	−2.6 (3)
O4—Co1—N2—C21	−150.16 (18)	C15—C16—C21—C20	179.2 (2)
O4—Co1—N2—C22	27.6 (2)	C17—C16—C21—N2	176.2 (2)
N2—Co1—O4—C28	−42.7 (2)	C17—C16—C21—C20	−2.0 (3)
Co1—O1—C1—C2	−66.1 (2)	C21—C16—C17—C18	1.6 (3)
Co1—O2—C14—C9	33.7 (3)	C16—C17—C18—C19	−0.1 (3)
Co1—O2—C14—C13	−147.8 (2)	C17—C18—C19—C20	−1.1 (4)
Co1—O3—C15—C16	−64.5 (2)	C18—C19—C20—C21	0.7 (4)
Co1—O4—C28—C23	35.7 (3)	C19—C20—C21—N2	−177.3 (2)
Co1—O4—C28—C27	−145.8 (2)	C19—C20—C21—C16	0.9 (3)
Co1—N1—C7—C2	−46.1 (2)	N2—C22—C23—C24	166.2 (2)
Co1—N1—C7—C6	130.47 (19)	N2—C22—C23—C28	−15.5 (4)
Co1—N1—C8—C9	−6.2 (3)	C22—C23—C24—C25	−178.9 (2)
C7—N1—C8—C9	169.6 (2)	C22—C23—C28—O4	−1.0 (4)
C8—N1—C7—C2	138.0 (2)	C22—C23—C28—C27	−179.5 (2)
C8—N1—C7—C6	−45.4 (3)	C24—C23—C28—O4	177.3 (2)
Co1—N2—C21—C16	−42.9 (2)	C24—C23—C28—C27	−1.3 (4)
Co1—N2—C21—C20	135.3 (2)	C28—C23—C24—C25	2.8 (4)
Co1—N2—C22—C23	−4.4 (3)	C23—C24—C25—C26	−2.2 (5)
C21—N2—C22—C23	173.4 (2)	C24—C25—C26—C27	0.2 (4)
C22—N2—C21—C16	139.3 (2)	C25—C26—C27—C28	1.3 (5)
C22—N2—C21—C20	−42.5 (3)	C26—C27—C28—O4	−179.3 (2)
O1—C1—C2—C3	−120.5 (2)	C26—C27—C28—C23	−0.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O8	0.82 (3)	1.75 (4)	2.557 (3)	171 (2)
O3—H13···O6^i	0.81 (5)	1.91 (5)	2.712 (3)	168 (4)
O8—H25···O5^ii	0.90 (2)	2.01 (2)	2.873 (2)	160 (3)
O8—H26···O5	0.92 (2)	1.84 (3)	2.745 (3)	169 (3)

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