Diaqua­bis[N-benzoyl-N'-(isonicotino­yl)hydrazine]dichloro­cobalt(II) dihydrate

In the title complex, [CoCl₂(C₁₃H₁₁N₃O₂)₂(H₂O)₂]·2H₂O, each Co^II atom occupies an inversion center and is coordinated by two water mol­ecules, two Cl^- anions and two N-benzoyl-N'-(isonicotino­yl)hydrazine ligands in a distorted octa­hedral geometry. The asymmetric unit contains two half-complexes. The three-dimensional supra­molecular architecture is stabilized by inter­molecular hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.077
• wR factor = 0.157
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10

   0 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

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

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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, 1997); software used to prepare material for publication: SHELXTL.

Diaquabis[N-benzoyl-N'-(isonicotinoyl)hydrazine]dichlorocobalt dihydrate

Crystal data

[CoCl2(C13H11N3O2)2(H2O)2]·2H2O	F(000) = 1412
Mr = 684.39	Dx = 1.464 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 927 reflections
a = 22.06 (4) Å	θ = 3.4–23.3°
b = 6.251 (11) Å	µ = 0.78 mm^−1
c = 22.73 (4) Å	T = 293 K
β = 97.89 (3)°	Block, dark red
V = 3105 (10) Å^3	0.24 × 0.20 × 0.16 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	5366 independent reflections
Radiation source: fine-focus sealed tube	3328 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.070
φ and ω scans	θmax = 25.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −26→20
Tmin = 0.835, Tmax = 0.885	k = −7→6
12298 measured reflections	l = −24→27

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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.157	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0407P)^2 + 6.4187P] where P = (Fo^2 + 2Fc^2)/3
5366 reflections	(Δ/σ)max < 0.001
391 parameters	Δρmax = 0.74 e Å^−3
0 restraints	Δρmin = −0.44 e Å^−3

Special details

Experimental. IR (KBr): 3405 (s), 3259 (s), 1676 (vs), 1649 (s), 1613 (s), 1560 (ms), 1516 (s), 1487 (ms), 1417 (m), 1305 (ms), 1292 (s), 1069 (m), 889 (m), 693 (m).

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	1.0000	0.5000	0.0000	0.0276 (3)
Co2	0.0000	0.5000	0.5000	0.0295 (3)
Cl1	1.05869 (8)	0.2020 (2)	0.05476 (7)	0.0412 (4)
Cl2	−0.06589 (7)	0.2430 (3)	0.43840 (7)	0.0424 (4)
O1	0.8183 (2)	0.8349 (8)	0.22143 (19)	0.0516 (13)
O2	0.87669 (19)	0.7211 (8)	0.34735 (17)	0.0440 (12)
O3	1.06707 (17)	0.7156 (6)	0.03444 (16)	0.0347 (10)
H3A	1.0919	0.6748	0.0643	0.042*
H3B	1.0508	0.8382	0.0370	0.042*
O4	0.34526 (18)	0.1715 (7)	0.37044 (17)	0.0369 (11)
O5	0.2125 (2)	0.1171 (8)	0.3124 (2)	0.0556 (14)
O6	−0.02991 (18)	0.7448 (6)	0.43901 (16)	0.0375 (11)
H6A	−0.0559	0.7060	0.4096	0.045*
H6B	−0.0325	0.8746	0.4499	0.045*
O7	0.2966 (2)	0.7834 (8)	0.4066 (2)	0.0626 (14)
H7A	0.3289	0.7070	0.4164	0.075*
H7B	0.2973	0.8639	0.3763	0.075*
O8	0.9072 (2)	0.1474 (8)	0.2948 (2)	0.0634 (15)
H8A	0.9173	0.1899	0.3301	0.076*
H8B	0.8944	0.0165	0.2936	0.076*
N1	0.9506 (2)	0.5466 (8)	0.0764 (2)	0.0319 (12)
N2	0.8312 (2)	0.4900 (9)	0.2519 (2)	0.0419 (14)
H2	0.8448	0.3650	0.2449	0.050*
N3	0.7996 (2)	0.5224 (9)	0.3005 (2)	0.0446 (15)
H3	0.7638	0.4678	0.3008	0.054*
N4	0.0743 (2)	0.4340 (8)	0.4482 (2)	0.0314 (12)
N5	0.2554 (2)	0.4470 (9)	0.3291 (2)	0.0411 (14)
H5C	0.2530	0.5725	0.3441	0.049*
N6	0.3032 (2)	0.3939 (9)	0.2970 (2)	0.0367 (13)
H6	0.3048	0.4506	0.2628	0.044*
C1	0.9186 (3)	0.3867 (10)	0.0960 (3)	0.0406 (17)
H1	0.9201	0.2527	0.0785	0.049*
C2	0.8827 (3)	0.4127 (11)	0.1421 (3)	0.0382 (16)
H2A	0.8612	0.2973	0.1547	0.046*
C3	0.8796 (3)	0.6088 (10)	0.1683 (2)	0.0311 (15)
C4	0.9141 (3)	0.7717 (11)	0.1491 (3)	0.0436 (17)
H4	0.9145	0.9056	0.1670	0.052*
C5	0.9480 (3)	0.7364 (10)	0.1034 (3)	0.0430 (17)
H5	0.9700	0.8500	0.0906	0.052*
C6	0.8402 (3)	0.6556 (11)	0.2160 (3)	0.0348 (16)
C7	0.8256 (3)	0.6397 (11)	0.3466 (3)	0.0366 (16)
C8	0.7889 (3)	0.6650 (11)	0.3973 (2)	0.0383 (17)
C9	0.7942 (3)	0.8555 (12)	0.4293 (3)	0.052 (2)
H9	0.8208	0.9605	0.4193	0.062*
C10	0.7605 (4)	0.8930 (15)	0.4762 (3)	0.068 (2)
H10	0.7629	1.0238	0.4959	0.082*
C11	0.7230 (4)	0.7270 (18)	0.4927 (3)	0.071 (3)
H11	0.7014	0.7461	0.5247	0.086*
C12	0.7182 (3)	0.5419 (15)	0.4627 (3)	0.064 (2)
H12	0.6926	0.4356	0.4739	0.077*
C13	0.7510 (3)	0.5034 (12)	0.4145 (3)	0.0501 (19)
H13	0.7474	0.3732	0.3945	0.060*
C14	0.1114 (3)	0.5879 (11)	0.4335 (3)	0.0465 (18)
H14	0.1062	0.7250	0.4479	0.056*
C15	0.1577 (3)	0.5566 (11)	0.3980 (3)	0.0447 (18)
H15	0.1825	0.6698	0.3895	0.054*
C16	0.1659 (3)	0.3547 (10)	0.3758 (2)	0.0288 (14)
C17	0.1276 (3)	0.1950 (10)	0.3909 (3)	0.0428 (17)
H17	0.1313	0.0570	0.3766	0.051*
C18	0.0841 (3)	0.2393 (10)	0.4272 (3)	0.0468 (18)
H18	0.0601	0.1270	0.4376	0.056*
C19	0.2132 (3)	0.2951 (11)	0.3357 (3)	0.0367 (16)
C20	0.3471 (3)	0.2519 (10)	0.3203 (3)	0.0332 (15)
C21	0.3962 (3)	0.2004 (10)	0.2838 (2)	0.0332 (15)
C22	0.4169 (3)	0.3450 (11)	0.2446 (3)	0.0449 (18)
H22	0.4000	0.4812	0.2403	0.054*
C23	0.4632 (3)	0.2862 (14)	0.2115 (3)	0.059 (2)
H23	0.4770	0.3848	0.1857	0.070*
C24	0.4882 (3)	0.0892 (14)	0.2164 (3)	0.057 (2)
H24	0.5186	0.0516	0.1937	0.069*
C25	0.4680 (3)	−0.0591 (12)	0.2559 (3)	0.0505 (19)
H25	0.4851	−0.1953	0.2597	0.061*
C26	0.4227 (3)	−0.0019 (11)	0.2891 (3)	0.0437 (17)
H26	0.4096	−0.1002	0.3154	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0343 (7)	0.0196 (6)	0.0291 (6)	0.0002 (6)	0.0052 (5)	−0.0027 (5)
Co2	0.0314 (7)	0.0271 (7)	0.0316 (6)	−0.0006 (6)	0.0100 (5)	−0.0046 (6)
Cl1	0.0503 (11)	0.0186 (8)	0.0508 (10)	0.0049 (8)	−0.0069 (8)	0.0002 (7)
Cl2	0.0450 (10)	0.0351 (9)	0.0465 (9)	−0.0038 (8)	0.0039 (8)	−0.0103 (8)
O1	0.049 (3)	0.059 (4)	0.048 (3)	0.023 (3)	0.012 (2)	−0.003 (2)
O2	0.033 (3)	0.063 (3)	0.034 (2)	−0.013 (3)	−0.001 (2)	0.002 (2)
O3	0.037 (2)	0.027 (2)	0.038 (2)	0.004 (2)	−0.0008 (19)	−0.002 (2)
O4	0.037 (3)	0.049 (3)	0.025 (2)	−0.004 (2)	0.0053 (19)	0.012 (2)
O5	0.045 (3)	0.065 (3)	0.061 (3)	−0.008 (3)	0.022 (2)	−0.037 (3)
O6	0.047 (3)	0.024 (2)	0.039 (2)	0.006 (2)	−0.005 (2)	−0.004 (2)
O7	0.055 (3)	0.050 (3)	0.084 (4)	−0.009 (3)	0.015 (3)	0.021 (3)
O8	0.094 (4)	0.041 (3)	0.056 (3)	−0.008 (3)	0.017 (3)	0.000 (3)
N1	0.045 (3)	0.024 (3)	0.028 (3)	0.000 (2)	0.010 (2)	−0.002 (2)
N2	0.040 (3)	0.051 (4)	0.038 (3)	−0.003 (3)	0.017 (3)	−0.015 (3)
N3	0.034 (3)	0.070 (4)	0.032 (3)	−0.018 (3)	0.012 (2)	−0.010 (3)
N4	0.037 (3)	0.026 (3)	0.033 (3)	−0.001 (2)	0.012 (2)	−0.001 (2)
N5	0.042 (3)	0.043 (4)	0.042 (3)	0.011 (3)	0.022 (3)	0.007 (3)
N6	0.037 (3)	0.051 (4)	0.025 (3)	0.012 (3)	0.017 (2)	0.017 (2)
C1	0.064 (5)	0.027 (4)	0.033 (4)	0.001 (3)	0.014 (3)	−0.009 (3)
C2	0.045 (4)	0.037 (4)	0.036 (4)	−0.007 (3)	0.016 (3)	0.000 (3)
C3	0.027 (4)	0.038 (4)	0.028 (3)	0.004 (3)	0.002 (3)	−0.004 (3)
C4	0.056 (5)	0.030 (4)	0.046 (4)	0.009 (4)	0.013 (3)	−0.009 (3)
C5	0.058 (5)	0.024 (4)	0.051 (4)	−0.002 (3)	0.025 (4)	0.003 (3)
C6	0.026 (4)	0.049 (5)	0.028 (3)	0.002 (3)	−0.002 (3)	−0.005 (3)
C7	0.035 (4)	0.045 (4)	0.029 (4)	−0.006 (3)	0.000 (3)	0.003 (3)
C8	0.036 (4)	0.059 (5)	0.018 (3)	0.003 (3)	0.001 (3)	−0.001 (3)
C9	0.063 (5)	0.059 (5)	0.035 (4)	−0.001 (4)	0.009 (4)	−0.011 (4)
C10	0.067 (6)	0.081 (6)	0.056 (5)	0.015 (5)	0.008 (4)	−0.023 (5)
C11	0.060 (6)	0.120 (9)	0.036 (4)	0.006 (6)	0.013 (4)	−0.014 (5)
C12	0.061 (5)	0.096 (7)	0.036 (4)	−0.013 (5)	0.014 (4)	0.011 (5)
C13	0.064 (5)	0.057 (5)	0.031 (3)	−0.015 (4)	0.012 (3)	0.002 (4)
C14	0.057 (5)	0.031 (4)	0.057 (4)	0.001 (4)	0.028 (4)	−0.007 (3)
C15	0.044 (4)	0.037 (4)	0.058 (4)	−0.006 (3)	0.026 (4)	−0.008 (3)
C16	0.019 (3)	0.037 (4)	0.029 (3)	0.001 (3)	0.002 (3)	0.001 (3)
C17	0.051 (4)	0.022 (3)	0.060 (4)	0.004 (3)	0.026 (4)	−0.009 (3)
C18	0.055 (5)	0.026 (4)	0.065 (5)	−0.004 (3)	0.028 (4)	0.001 (3)
C19	0.033 (4)	0.049 (4)	0.028 (3)	0.005 (3)	0.004 (3)	−0.005 (3)
C20	0.035 (4)	0.034 (4)	0.031 (3)	−0.001 (3)	0.003 (3)	−0.003 (3)
C21	0.033 (4)	0.038 (4)	0.031 (3)	0.006 (3)	0.011 (3)	−0.002 (3)
C22	0.037 (4)	0.048 (5)	0.052 (4)	0.010 (3)	0.014 (3)	0.011 (4)
C23	0.040 (5)	0.078 (6)	0.062 (5)	0.011 (4)	0.021 (4)	0.025 (5)
C24	0.033 (4)	0.083 (6)	0.059 (5)	0.009 (4)	0.015 (4)	−0.014 (5)
C25	0.041 (4)	0.042 (4)	0.069 (5)	0.014 (4)	0.010 (4)	−0.005 (4)
C26	0.041 (4)	0.037 (4)	0.054 (4)	0.002 (4)	0.010 (3)	0.008 (4)

Geometric parameters (Å, º)

Co1—O3	2.074 (4)	C2—C3	1.369 (9)
Co1—O3^i	2.074 (4)	C2—H2A	0.9300
Co1—N1^i	2.193 (5)	C3—C4	1.377 (9)
Co1—N1	2.193 (5)	C3—C6	1.508 (8)
Co1—Cl1	2.501 (3)	C4—C5	1.379 (8)
Co1—Cl1^i	2.501 (3)	C4—H4	0.9300
Co2—O6^ii	2.109 (5)	C5—H5	0.9300
Co2—O6	2.109 (5)	C7—C8	1.507 (8)
Co2—N4^ii	2.185 (5)	C8—C9	1.391 (9)
Co2—N4	2.185 (5)	C8—C13	1.401 (9)
Co2—Cl2	2.469 (3)	C9—C10	1.399 (10)
Co2—Cl2^ii	2.469 (3)	C9—H9	0.9300
O1—C6	1.233 (8)	C10—C11	1.411 (12)
O2—C7	1.234 (7)	C10—H10	0.9300
O3—H3A	0.8518	C11—C12	1.340 (12)
O3—H3B	0.8514	C11—H11	0.9300
O4—C20	1.251 (7)	C12—C13	1.414 (9)
O5—C19	1.232 (8)	C12—H12	0.9300
O6—H6A	0.8542	C13—H13	0.9300
O6—H6B	0.8525	C14—C15	1.400 (8)
O7—H7A	0.8612	C14—H14	0.9300
O7—H7B	0.8548	C15—C16	1.380 (9)
O8—H8A	0.8465	C15—H15	0.9300
O8—H8B	0.8650	C16—C17	1.382 (8)
N1—C1	1.336 (8)	C16—C19	1.522 (8)
N1—C5	1.340 (8)	C17—C18	1.376 (8)
N2—C6	1.350 (8)	C17—H17	0.9300
N2—N3	1.399 (6)	C18—H18	0.9300
N2—H2	0.8600	C20—C21	1.487 (8)
N3—C7	1.342 (8)	C21—C22	1.391 (8)
N3—H3	0.8600	C21—C26	1.391 (9)
N4—C14	1.336 (8)	C22—C23	1.398 (9)
N4—C18	1.336 (8)	C22—H22	0.9300
N5—C19	1.353 (8)	C23—C24	1.347 (10)
N5—N6	1.401 (6)	C23—H23	0.9300
N5—H5C	0.8600	C24—C25	1.407 (10)
N6—C20	1.367 (8)	C24—H24	0.9300
N6—H6	0.8600	C25—C26	1.379 (9)
C1—C2	1.406 (8)	C25—H25	0.9300
C1—H1	0.9300	C26—H26	0.9300
O3—Co1—O3^i	179.998 (1)	C5—C4—H4	120.0
O3—Co1—N1^i	88.81 (19)	N1—C5—C4	123.3 (6)
O3^i—Co1—N1^i	91.19 (19)	N1—C5—H5	118.4
O3—Co1—N1	91.19 (19)	C4—C5—H5	118.4
O3^i—Co1—N1	88.81 (19)	O1—C6—N2	122.9 (6)
N1^i—Co1—N1	179.999 (1)	O1—C6—C3	121.4 (6)
O3—Co1—Cl1	90.14 (17)	N2—C6—C3	115.7 (6)
O3^i—Co1—Cl1	89.86 (17)	O2—C7—N3	121.9 (6)
N1^i—Co1—Cl1	90.91 (16)	O2—C7—C8	122.1 (6)
N1—Co1—Cl1	89.09 (16)	N3—C7—C8	116.0 (6)
O3—Co1—Cl1^i	89.86 (17)	C9—C8—C13	118.9 (6)
O3^i—Co1—Cl1^i	90.14 (17)	C9—C8—C7	118.3 (6)
N1^i—Co1—Cl1^i	89.09 (16)	C13—C8—C7	122.8 (6)
N1—Co1—Cl1^i	90.91 (16)	C8—C9—C10	121.7 (7)
Cl1—Co1—Cl1^i	180.0	C8—C9—H9	119.1
O6^ii—Co2—O6	179.998 (1)	C10—C9—H9	119.1
O6^ii—Co2—N4^ii	88.45 (19)	C9—C10—C11	118.1 (8)
O6—Co2—N4^ii	91.55 (19)	C9—C10—H10	120.9
O6^ii—Co2—N4	91.55 (19)	C11—C10—H10	120.9
O6—Co2—N4	88.44 (19)	C12—C11—C10	120.5 (7)
N4^ii—Co2—N4	179.998 (1)	C12—C11—H11	119.7
O6^ii—Co2—Cl2	90.41 (17)	C10—C11—H11	119.7
O6—Co2—Cl2	89.59 (17)	C11—C12—C13	121.9 (8)
N4^ii—Co2—Cl2	90.10 (17)	C11—C12—H12	119.0
N4—Co2—Cl2	89.90 (17)	C13—C12—H12	119.0
O6^ii—Co2—Cl2^ii	89.59 (17)	C8—C13—C12	118.8 (7)
O6—Co2—Cl2^ii	90.41 (17)	C8—C13—H13	120.6
N4^ii—Co2—Cl2^ii	89.90 (17)	C12—C13—H13	120.6
N4—Co2—Cl2^ii	90.10 (17)	N4—C14—C15	124.4 (6)
Cl2—Co2—Cl2^ii	180.0	N4—C14—H14	117.8
Co1—O3—H3A	117.0	C15—C14—H14	117.8
Co1—O3—H3B	109.0	C16—C15—C14	118.8 (6)
H3A—O3—H3B	116.5	C16—C15—H15	120.6
Co2—O6—H6A	115.1	C14—C15—H15	120.6
Co2—O6—H6B	121.8	C15—C16—C17	117.0 (5)
H6A—O6—H6B	115.7	C15—C16—C19	125.3 (6)
H7A—O7—H7B	115.5	C17—C16—C19	117.7 (6)
H8A—O8—H8B	111.6	C18—C17—C16	120.3 (6)
C1—N1—C5	116.8 (5)	C18—C17—H17	119.9
C1—N1—Co1	120.5 (4)	C16—C17—H17	119.9
C5—N1—Co1	122.5 (4)	N4—C18—C17	123.9 (6)
C6—N2—N3	119.8 (5)	N4—C18—H18	118.0
C6—N2—H2	120.1	C17—C18—H18	118.0
N3—N2—H2	120.1	O5—C19—N5	123.6 (6)
C7—N3—N2	119.3 (5)	O5—C19—C16	120.6 (6)
C7—N3—H3	120.4	N5—C19—C16	115.7 (6)
N2—N3—H3	120.4	O4—C20—N6	120.3 (5)
C14—N4—C18	115.6 (5)	O4—C20—C21	122.5 (6)
C14—N4—Co2	122.0 (4)	N6—C20—C21	117.2 (5)
C18—N4—Co2	122.4 (4)	C22—C21—C26	118.4 (6)
C19—N5—N6	118.1 (5)	C22—C21—C20	123.1 (6)
C19—N5—H5C	121.0	C26—C21—C20	118.6 (6)
N6—N5—H5C	121.0	C21—C22—C23	120.2 (6)
C20—N6—N5	119.8 (5)	C21—C22—H22	119.9
C20—N6—H6	120.1	C23—C22—H22	119.9
N5—N6—H6	120.1	C24—C23—C22	121.1 (7)
N1—C1—C2	122.7 (6)	C24—C23—H23	119.4
N1—C1—H1	118.7	C22—C23—H23	119.4
C2—C1—H1	118.7	C23—C24—C25	119.5 (7)
C3—C2—C1	119.6 (6)	C23—C24—H24	120.2
C3—C2—H2A	120.2	C25—C24—H24	120.2
C1—C2—H2A	120.2	C26—C25—C24	119.7 (7)
C2—C3—C4	117.5 (5)	C26—C25—H25	120.1
C2—C3—C6	123.7 (6)	C24—C25—H25	120.1
C4—C3—C6	118.8 (6)	C25—C26—C21	121.0 (6)
C3—C4—C5	120.0 (6)	C25—C26—H26	119.5
C3—C4—H4	120.0	C21—C26—H26	119.5
O3—Co1—N1—C1	−148.3 (5)	N3—C7—C8—C13	34.5 (9)
O3^i—Co1—N1—C1	31.7 (5)	C13—C8—C9—C10	−3.0 (10)
Cl1—Co1—N1—C1	−58.2 (5)	C7—C8—C9—C10	178.5 (6)
Cl1^i—Co1—N1—C1	121.8 (5)	C8—C9—C10—C11	3.4 (11)
O3—Co1—N1—C5	35.6 (5)	C9—C10—C11—C12	−2.4 (12)
O3^i—Co1—N1—C5	−144.3 (5)	C10—C11—C12—C13	1.2 (13)
Cl1—Co1—N1—C5	125.8 (5)	C9—C8—C13—C12	1.6 (10)
Cl1^i—Co1—N1—C5	−54.2 (5)	C7—C8—C13—C12	−180.0 (6)
C6—N2—N3—C7	−68.8 (8)	C11—C12—C13—C8	−0.7 (11)
O6^ii—Co2—N4—C14	−128.3 (5)	C18—N4—C14—C15	0.9 (10)
O6—Co2—N4—C14	51.7 (5)	Co2—N4—C14—C15	−176.7 (5)
Cl2—Co2—N4—C14	141.3 (5)	N4—C14—C15—C16	0.5 (10)
Cl2^ii—Co2—N4—C14	−38.7 (5)	C14—C15—C16—C17	−0.5 (9)
O6^ii—Co2—N4—C18	54.4 (5)	C14—C15—C16—C19	178.8 (6)
O6—Co2—N4—C18	−125.6 (5)	C15—C16—C17—C18	−0.8 (9)
Cl2—Co2—N4—C18	−36.0 (5)	C19—C16—C17—C18	179.9 (6)
Cl2^ii—Co2—N4—C18	144.0 (5)	C14—N4—C18—C17	−2.3 (10)
C19—N5—N6—C20	−69.3 (7)	Co2—N4—C18—C17	175.3 (5)
C5—N1—C1—C2	0.9 (9)	C16—C17—C18—N4	2.3 (11)
Co1—N1—C1—C2	−175.4 (5)	N6—N5—C19—O5	−4.2 (9)
N1—C1—C2—C3	0.3 (10)	N6—N5—C19—C16	174.4 (5)
C1—C2—C3—C4	−2.1 (9)	C15—C16—C19—O5	−171.3 (6)
C1—C2—C3—C6	177.0 (6)	C17—C16—C19—O5	7.9 (9)
C2—C3—C4—C5	2.7 (9)	C15—C16—C19—N5	10.0 (9)
C6—C3—C4—C5	−176.5 (6)	C17—C16—C19—N5	−170.7 (6)
C1—N1—C5—C4	−0.3 (10)	N5—N6—C20—O4	−1.0 (9)
Co1—N1—C5—C4	175.9 (5)	N5—N6—C20—C21	179.4 (5)
C3—C4—C5—N1	−1.6 (10)	O4—C20—C21—C22	−149.1 (6)
N3—N2—C6—O1	−4.9 (9)	N6—C20—C21—C22	30.5 (9)
N3—N2—C6—C3	174.6 (5)	O4—C20—C21—C26	31.0 (9)
C2—C3—C6—O1	−149.5 (6)	N6—C20—C21—C26	−149.4 (6)
C4—C3—C6—O1	29.6 (9)	C26—C21—C22—C23	0.0 (10)
C2—C3—C6—N2	30.9 (9)	C20—C21—C22—C23	−179.9 (6)
C4—C3—C6—N2	−150.0 (6)	C21—C22—C23—C24	0.7 (11)
N2—N3—C7—O2	0.3 (10)	C22—C23—C24—C25	−0.9 (11)
N2—N3—C7—C8	−179.4 (5)	C23—C24—C25—C26	0.3 (11)
O2—C7—C8—C9	33.3 (9)	C24—C25—C26—C21	0.4 (10)
N3—C7—C8—C9	−147.0 (6)	C22—C21—C26—C25	−0.6 (10)
O2—C7—C8—C13	−145.2 (7)	C20—C21—C26—C25	179.3 (6)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O8	0.86	2.15	2.811 (9)	134
N3—H3···O1^iii	0.86	1.99	2.834 (8)	165
N5—H5C···O7	0.86	2.08	2.813 (9)	143
N6—H6···O5^iv	0.86	1.99	2.831 (8)	165
O3—H3A···O4^v	0.85	1.89	2.710 (7)	163
O3—H3B···Cl1^vi	0.85	2.31	3.085 (7)	151
O6—H6A···O2^vii	0.85	1.91	2.726 (7)	160
O6—H6B···Cl2^vi	0.85	2.42	3.212 (7)	155
O7—H7A···Cl1^v	0.86	2.48	3.233 (8)	147
O7—H7B···O4^vi	0.85	2.21	2.821 (8)	129
O8—H8A···Cl2^viii	0.85	2.46	3.291 (8)	167
O8—H8B···O1^ix	0.86	2.46	3.090 (9)	130
O8—H8B···O2^ix	0.86	2.28	3.033 (9)	146

Symmetry codes: (iii) −x+3/2, y−1/2, −z+1/2; (iv) −x+1/2, y+1/2, −z+1/2; (v) −x+3/2, y+1/2, −z+1/2; (vi) x, y+1, z; (vii) x−1, y, z; (viii) x+1, y, z; (ix) x, y−1, z.