Tris(ethylenediamine)cobalt(II) bis(tetra-hydroxypentaborate) dihydrate.

The novel pentaborate with a transition-metal complex as counter-cation and with water of crystallization, tris(ethylenediamine)cobalt(II) bis[4,4',6,6'-tetrahydroxy-2,2'-spirobi(cyclotriboroxane)(1-)] dihydrate, [Co(C(2)H(8)N(2))(3)][B(5)O(6)(OH)(4)](2)·2H(2)O, forms a three-dimensional supra-molecular framework through O-H⋯O hydrogen bonding among the [B(5)O(6)(OH)(4)](-) anions with large channels along the a axis in which the templating [Co(en)(3)](2+) cations (en = ethylenediamine) and water mol-ecules are located. The crystal packing is consolidated by additional O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For related structures, see: Liu et al. (2006 ▶); Sung et al. (2000 ▶); Touboul et al. (2003 ▶); Wang et al. (2005 ▶, 2006 ▶); Zhang et al. (2004 ▶). For background to the applications of borate compounds, see: Becker (1998 ▶). For related literature, see: Li et al. (1995 ▶, 2007 ▶).

Experimental

Crystal data

[Co(C2H8N2)3][B5O6(OH)4]2·2H2O

M = 711.44

Monoclinic,

a = 8.504 (4) Å

b = 23.127 (10) Å

c = 15.306 (7) Å

β = 93.549 (7)°

V = 3004 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.67 mm−1

T = 293 K

0.50 × 0.47 × 0.29 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan SADABS (Bruker, 2001 ▶) T min = 0.732, T max = 0.830

15470 measured reflections

5252 independent reflections

2809 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.232

S = 1.02

5252 reflections

406 parameters

9 restraints

H-atom parameters constrained

Δρmax = 1.68 e Å−3

Δρmin = −0.70 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809007296/pv2140sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007296/pv2140Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Co(C2H8N2)3][B5O6(OH)4]2·2H2O	F(000) = 1468
Mr = 711.44	Dx = 1.573 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2705 reflections
a = 8.504 (4) Å	θ = 2.2–23.6°
b = 23.127 (10) Å	µ = 0.67 mm−1
c = 15.306 (7) Å	T = 293 K
β = 93.549 (7)°	Columnar, orange
V = 3004 (2) Å3	0.50 × 0.47 × 0.29 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	5252 independent reflections
Radiation source: fine-focus sealed tube	2809 reflections with I > 2σ(I)
graphite	Rint = 0.054
phi and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan SADABS (Bruker, 2001)	h = −8→10
Tmin = 0.732, Tmax = 0.830	k = −27→27
15470 measured reflections	l = −18→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.232	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.1233P)2 + 1.7881P] where P = (Fo2 + 2Fc2)/3
5252 reflections	(Δ/σ)max < 0.001
406 parameters	Δρmax = 1.68 e Å−3
9 restraints	Δρmin = −0.70 e Å−3

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.

	x	y	z	Uiso*/Ueq
Co1	0.43617 (9)	0.63869 (4)	0.77983 (5)	0.0537 (3)
B1	0.1368 (7)	0.3764 (3)	0.5439 (4)	0.0351 (15)
B2	−0.0462 (7)	0.3228 (3)	0.4381 (4)	0.0362 (14)
B3	−0.0621 (8)	0.4253 (3)	0.4431 (4)	0.0454 (17)
B4	0.4227 (8)	0.3736 (3)	0.5801 (4)	0.0438 (17)
B5	0.2513 (7)	0.3623 (3)	0.6949 (4)	0.0417 (16)
B6	0.9279 (7)	0.3764 (2)	0.9264 (4)	0.0354 (15)
B7	0.6432 (8)	0.3663 (3)	0.8895 (4)	0.0427 (16)
B8	0.8133 (8)	0.3742 (3)	0.7739 (4)	0.0456 (17)
B9	1.1260 (8)	0.4291 (3)	1.0232 (4)	0.0440 (17)
B10	1.1424 (8)	0.3266 (3)	1.0171 (4)	0.0386 (15)
N1	0.4478 (7)	0.5823 (3)	0.8935 (3)	0.0678 (16)
H1A	0.5470	0.5814	0.9176	0.081*
H1B	0.3846	0.5960	0.9337	0.081*
N2	0.4191 (7)	0.5563 (3)	0.7164 (4)	0.0756 (18)
H2A	0.3213	0.5514	0.6915	0.091*
H2B	0.4878	0.5545	0.6741	0.091*
N3	0.1854 (6)	0.6528 (3)	0.7892 (4)	0.0673 (16)
H3A	0.1359	0.6498	0.7357	0.081*
H3B	0.1462	0.6255	0.8237	0.081*
N4	0.4324 (7)	0.7182 (3)	0.8632 (4)	0.084 (2)
H4A	0.4961	0.7131	0.9118	0.100*
H4B	0.4689	0.7485	0.8336	0.100*
N5	0.4420 (6)	0.6870 (3)	0.6575 (4)	0.0741 (18)
H5A	0.4242	0.6628	0.6119	0.089*
H5B	0.3657	0.7140	0.6550	0.089*
N6	0.6878 (6)	0.6488 (3)	0.7685 (4)	0.0733 (18)
H6A	0.7290	0.6692	0.8145	0.088*
H6B	0.7339	0.6137	0.7697	0.088*
O1	0.0701 (4)	0.32294 (14)	0.5030 (2)	0.0375 (9)
O2	−0.1085 (5)	0.37366 (15)	0.4055 (3)	0.0552 (12)
O3	0.0455 (4)	0.42693 (14)	0.5118 (2)	0.0400 (9)
O4	0.3000 (4)	0.38294 (16)	0.5216 (2)	0.0426 (10)
O5	0.4009 (4)	0.3580 (2)	0.6644 (2)	0.0558 (12)
O6	0.1250 (4)	0.37288 (15)	0.6392 (2)	0.0373 (9)
O7	−0.1035 (5)	0.27447 (15)	0.3988 (3)	0.0503 (11)
H7	−0.0574	0.2462	0.4202	0.075*
O8	−0.1303 (6)	0.47363 (17)	0.4077 (3)	0.0774 (17)
H8	−0.0942	0.5022	0.4336	0.116*
O9	0.5727 (5)	0.3794 (2)	0.5539 (3)	0.0638 (13)
H9	0.6359	0.3723	0.5951	0.096*
O10	0.2410 (5)	0.3565 (2)	0.7824 (2)	0.0609 (13)
H10	0.1489	0.3600	0.7944	0.091*
O11	0.7650 (4)	0.37226 (15)	0.9490 (2)	0.0409 (9)
O12	0.6659 (5)	0.3664 (2)	0.8021 (3)	0.0683 (15)
O13	0.9406 (4)	0.37903 (14)	0.8307 (2)	0.0377 (9)
O14	0.9985 (4)	0.42903 (14)	0.9664 (2)	0.0399 (9)
O15	1.2021 (5)	0.37858 (15)	1.0477 (3)	0.0507 (11)
O16	1.0164 (4)	0.32445 (15)	0.9591 (2)	0.0407 (10)
O17	0.4946 (4)	0.36107 (19)	0.9168 (3)	0.0580 (12)
H17	0.4319	0.3579	0.8742	0.087*
O18	0.8250 (5)	0.3745 (2)	0.6850 (2)	0.0691 (15)
H18	0.9178	0.3779	0.6740	0.104*
O19	1.1888 (5)	0.47805 (17)	1.0601 (3)	0.0717 (15)
H19	1.1376	0.5061	1.0422	0.108*
O20	1.2153 (4)	0.27831 (15)	1.0506 (2)	0.0466 (10)
H20	1.1709	0.2495	1.0300	0.070*
O21	0.3273 (11)	0.4825 (3)	0.4013 (6)	0.177 (4)
H1	0.3714	0.4538	0.4274	0.213*
H2	0.2390	0.4810	0.4243	0.213*
O22	0.0595 (11)	0.4556 (4)	0.2344 (6)	0.202 (4)
H3	0.1211	0.4802	0.2134	0.243*
H4	−0.0011	0.4738	0.2670	0.243*
C1	0.3987 (12)	0.5242 (4)	0.8680 (5)	0.097 (3)
H1C	0.2847	0.5215	0.8662	0.117*
H1D	0.4418	0.4966	0.9107	0.117*
C2	0.4543 (13)	0.5106 (4)	0.7813 (6)	0.109 (3)
H2C	0.5673	0.5043	0.7869	0.131*
H2D	0.4054	0.4749	0.7604	0.131*
C3	0.1559 (10)	0.7101 (4)	0.8256 (6)	0.103 (3)
H3C	0.1426	0.7377	0.7780	0.124*
H3D	0.0583	0.7090	0.8552	0.124*
C4	0.2810 (9)	0.7299 (3)	0.8866 (6)	0.083 (2)
H4C	0.2704	0.7713	0.8937	0.100*
H4D	0.2670	0.7122	0.9430	0.100*
C5	0.5921 (9)	0.7141 (4)	0.6522 (5)	0.078 (2)
H5C	0.5925	0.7504	0.6839	0.094*
H5D	0.6086	0.7227	0.5914	0.094*
C6	0.7205 (9)	0.6782 (5)	0.6879 (5)	0.105 (3)
H6C	0.7448	0.6495	0.6445	0.126*
H6D	0.8132	0.7022	0.6986	0.126*

	U11	U22	U33	U12	U13	U23
Co1	0.0375 (5)	0.0835 (7)	0.0385 (5)	−0.0089 (4)	−0.0091 (3)	0.0043 (4)
B1	0.035 (3)	0.035 (4)	0.034 (3)	−0.001 (3)	−0.013 (3)	0.000 (3)
B2	0.039 (3)	0.035 (4)	0.034 (3)	0.001 (3)	−0.008 (3)	0.001 (3)
B3	0.051 (4)	0.035 (4)	0.048 (4)	0.005 (3)	−0.024 (3)	−0.006 (3)
B4	0.035 (4)	0.057 (5)	0.038 (4)	0.000 (3)	−0.005 (3)	−0.004 (3)
B5	0.033 (3)	0.060 (4)	0.031 (3)	0.004 (3)	−0.009 (3)	−0.003 (3)
B6	0.040 (4)	0.031 (4)	0.032 (3)	0.002 (3)	−0.018 (3)	−0.002 (2)
B7	0.043 (4)	0.048 (4)	0.036 (4)	0.002 (3)	−0.008 (3)	0.000 (3)
B8	0.035 (4)	0.063 (5)	0.036 (4)	0.006 (3)	−0.011 (3)	−0.002 (3)
B9	0.043 (4)	0.034 (4)	0.051 (4)	0.003 (3)	−0.023 (3)	−0.006 (3)
B10	0.044 (4)	0.032 (4)	0.038 (3)	0.004 (3)	−0.007 (3)	−0.003 (3)
N1	0.060 (4)	0.088 (5)	0.055 (3)	0.001 (3)	−0.009 (3)	−0.003 (3)
N2	0.079 (4)	0.095 (5)	0.051 (3)	0.008 (4)	−0.007 (3)	−0.015 (3)
N3	0.053 (3)	0.086 (4)	0.062 (4)	−0.006 (3)	0.001 (3)	0.000 (3)
N4	0.069 (4)	0.108 (5)	0.074 (4)	−0.009 (4)	0.005 (3)	−0.029 (4)
N5	0.052 (4)	0.108 (5)	0.061 (4)	0.001 (3)	−0.002 (3)	0.016 (3)
N6	0.046 (3)	0.125 (5)	0.048 (3)	0.002 (3)	−0.007 (3)	−0.002 (3)
O1	0.041 (2)	0.031 (2)	0.039 (2)	0.0017 (16)	−0.0158 (17)	−0.0017 (16)
O2	0.065 (3)	0.036 (2)	0.059 (3)	0.0065 (19)	−0.043 (2)	−0.0046 (19)
O3	0.044 (2)	0.032 (2)	0.041 (2)	0.0039 (17)	−0.0202 (17)	−0.0004 (16)
O4	0.035 (2)	0.057 (3)	0.034 (2)	−0.0018 (18)	−0.0074 (17)	0.0067 (17)
O5	0.031 (2)	0.103 (3)	0.033 (2)	0.011 (2)	−0.0068 (17)	0.008 (2)
O6	0.0293 (19)	0.048 (2)	0.033 (2)	0.0043 (16)	−0.0077 (15)	−0.0029 (16)
O7	0.058 (2)	0.027 (2)	0.061 (3)	0.0002 (18)	−0.033 (2)	−0.0043 (18)
O8	0.103 (4)	0.031 (2)	0.088 (3)	0.012 (2)	−0.072 (3)	−0.006 (2)
O9	0.035 (2)	0.111 (4)	0.045 (3)	0.001 (2)	−0.0018 (19)	0.007 (2)
O10	0.033 (2)	0.121 (4)	0.027 (2)	0.007 (2)	−0.0088 (16)	0.004 (2)
O11	0.041 (2)	0.051 (2)	0.030 (2)	−0.0008 (17)	−0.0092 (17)	0.0005 (16)
O12	0.033 (2)	0.142 (5)	0.029 (2)	−0.002 (2)	−0.0065 (18)	−0.008 (2)
O13	0.035 (2)	0.044 (2)	0.033 (2)	−0.0007 (16)	−0.0104 (16)	−0.0009 (16)
O14	0.045 (2)	0.029 (2)	0.043 (2)	0.0052 (17)	−0.0198 (17)	−0.0065 (16)
O15	0.050 (2)	0.033 (2)	0.064 (3)	0.0054 (18)	−0.034 (2)	−0.0065 (18)
O16	0.044 (2)	0.029 (2)	0.046 (2)	0.0010 (16)	−0.0230 (18)	−0.0024 (16)
O17	0.034 (2)	0.102 (4)	0.038 (2)	−0.013 (2)	−0.0004 (18)	−0.003 (2)
O18	0.031 (2)	0.146 (5)	0.029 (2)	−0.001 (2)	−0.0071 (17)	−0.002 (2)
O19	0.075 (3)	0.033 (2)	0.099 (4)	0.006 (2)	−0.056 (3)	−0.013 (2)
O20	0.046 (2)	0.034 (2)	0.055 (2)	0.0063 (17)	−0.0273 (19)	−0.0023 (18)
O21	0.229 (10)	0.141 (7)	0.173 (8)	0.035 (6)	0.103 (7)	0.032 (6)
O22	0.230 (8)	0.187 (7)	0.200 (7)	−0.038 (6)	0.088 (6)	−0.015 (6)
C1	0.136 (8)	0.084 (7)	0.071 (6)	−0.001 (6)	0.006 (5)	0.011 (5)
C2	0.161 (10)	0.066 (6)	0.099 (7)	0.003 (6)	−0.012 (7)	−0.001 (5)
C3	0.080 (6)	0.143 (9)	0.087 (6)	0.024 (6)	0.007 (5)	−0.025 (6)
C4	0.079 (6)	0.068 (5)	0.103 (6)	0.000 (4)	0.005 (5)	−0.003 (5)
C5	0.077 (5)	0.097 (6)	0.061 (5)	−0.022 (5)	0.003 (4)	0.009 (4)
C6	0.058 (5)	0.184 (11)	0.072 (6)	−0.014 (6)	0.005 (4)	0.011 (6)

Co1—N2	2.139 (6)	N2—H2A	0.9000
Co1—N6	2.170 (6)	N2—H2B	0.9000
Co1—N3	2.171 (6)	N3—C3	1.465 (10)
Co1—N1	2.172 (6)	N3—H3A	0.9000
Co1—N5	2.183 (5)	N3—H3B	0.9000
Co1—N4	2.241 (6)	N4—C4	1.384 (9)
B1—O4	1.457 (7)	N4—H4A	0.9000
B1—O6	1.470 (7)	N4—H4B	0.9000
B1—O3	1.471 (7)	N5—C5	1.429 (9)
B1—O1	1.483 (7)	N5—H5A	0.9000
B2—O7	1.347 (7)	N5—H5B	0.9000
B2—O1	1.357 (6)	N6—C6	1.451 (10)
B2—O2	1.370 (7)	N6—H6A	0.9000
B3—O3	1.351 (6)	N6—H6B	0.9000
B3—O8	1.356 (7)	O7—H7	0.8200
B3—O2	1.373 (7)	O8—H8	0.8200
B4—O4	1.350 (7)	O9—H9	0.8200
B4—O5	1.363 (8)	O10—H10	0.8200
B4—O9	1.367 (8)	O17—H17	0.8200
B5—O6	1.352 (7)	O18—H18	0.8200
B5—O10	1.355 (7)	O19—H19	0.8200
B5—O5	1.385 (8)	O20—H20	0.8200
B6—O11	1.451 (8)	O21—H1	0.8502
B6—O14	1.473 (6)	O21—H2	0.8503
B6—O13	1.478 (7)	O22—H3	0.8499
B6—O16	1.488 (7)	O22—H4	0.8501
B7—O11	1.344 (7)	C1—C2	1.470 (10)
B7—O17	1.361 (8)	C1—H1C	0.9700
B7—O12	1.364 (8)	C1—H1D	0.9700
B8—O13	1.350 (7)	C2—H2C	0.9700
B8—O12	1.363 (8)	C2—H2D	0.9700
B8—O18	1.371 (8)	C3—C4	1.445 (10)
B9—O14	1.347 (6)	C3—H3C	0.9700
B9—O19	1.359 (7)	C3—H3D	0.9700
B9—O15	1.377 (7)	C4—H4C	0.9700
B10—O16	1.349 (7)	C4—H4D	0.9700
B10—O20	1.362 (7)	C5—C6	1.452 (10)
B10—O15	1.376 (7)	C5—H5C	0.9700
N1—C1	1.452 (10)	C5—H5D	0.9700
N1—H1A	0.9000	C6—H6C	0.9700
N1—H1B	0.9000	C6—H6D	0.9700
N2—C2	1.470 (10)
N2—Co1—N6	95.7 (3)	Co1—N4—H4B	109.5
N2—Co1—N3	97.2 (2)	H4A—N4—H4B	108.1
N6—Co1—N3	165.1 (3)	C5—N5—Co1	110.0 (4)
N2—Co1—N1	80.0 (2)	C5—N5—H5A	109.7
N6—Co1—N1	97.6 (2)	Co1—N5—H5A	109.7
N3—Co1—N1	91.9 (2)	C5—N5—H5B	109.7
N2—Co1—N5	94.0 (2)	Co1—N5—H5B	109.7
N6—Co1—N5	78.6 (2)	H5A—N5—H5B	108.2
N3—Co1—N5	93.1 (2)	C6—N6—Co1	111.1 (4)
N1—Co1—N5	172.7 (2)	C6—N6—H6A	109.4
N2—Co1—N4	170.7 (2)	Co1—N6—H6A	109.4
N6—Co1—N4	90.3 (2)	C6—N6—H6B	109.4
N3—Co1—N4	77.9 (2)	Co1—N6—H6B	109.4
N1—Co1—N4	92.2 (2)	H6A—N6—H6B	108.0
N5—Co1—N4	94.1 (3)	B2—O1—B1	123.6 (4)
O4—B1—O6	111.3 (4)	B2—O2—B3	120.0 (4)
O4—B1—O3	109.2 (4)	B3—O3—B1	123.8 (4)
O6—B1—O3	108.0 (4)	B4—O4—B1	122.4 (5)
O4—B1—O1	109.4 (5)	B4—O5—B5	118.7 (5)
O6—B1—O1	109.0 (4)	B5—O6—B1	122.3 (5)
O3—B1—O1	109.9 (4)	B2—O7—H7	109.5
O7—B2—O1	123.7 (5)	B3—O8—H8	109.5
O7—B2—O2	115.4 (4)	B4—O9—H9	109.5
O1—B2—O2	120.8 (5)	B5—O10—H10	109.5
O3—B3—O8	122.7 (5)	B7—O11—B6	123.5 (5)
O3—B3—O2	120.9 (5)	B8—O12—B7	120.0 (5)
O8—B3—O2	116.4 (4)	B8—O13—B6	122.0 (5)
O4—B4—O5	121.7 (6)	B9—O14—B6	124.1 (4)
O4—B4—O9	119.1 (6)	B10—O15—B9	119.4 (4)
O5—B4—O9	119.2 (5)	B10—O16—B6	123.8 (4)
O6—B5—O10	122.9 (5)	B7—O17—H17	109.5
O6—B5—O5	120.8 (5)	B8—O18—H18	109.5
O10—B5—O5	116.3 (5)	B9—O19—H19	109.5
O11—B6—O14	109.0 (5)	B10—O20—H20	109.5
O11—B6—O13	111.6 (4)	H2—O21—H1	98.5
O14—B6—O13	109.0 (4)	H3—O22—H4	107.6
O11—B6—O16	109.7 (5)	N1—C1—C2	109.7 (7)
O14—B6—O16	110.0 (4)	N1—C1—H1C	109.7
O13—B6—O16	107.5 (4)	C2—C1—H1C	109.7
O11—B7—O17	119.5 (5)	N1—C1—H1D	109.7
O11—B7—O12	121.0 (6)	C2—C1—H1D	109.7
O17—B7—O12	119.5 (5)	H1C—C1—H1D	108.2
O13—B8—O12	121.6 (6)	N2—C2—C1	113.1 (7)
O13—B8—O18	122.3 (6)	N2—C2—H2C	109.0
O12—B8—O18	116.1 (5)	C1—C2—H2C	109.0
O14—B9—O19	123.4 (5)	N2—C2—H2D	109.0
O14—B9—O15	121.4 (5)	C1—C2—H2D	109.0
O19—B9—O15	115.3 (4)	H2C—C2—H2D	107.8
O16—B10—O20	122.8 (5)	C4—C3—N3	113.3 (7)
O16—B10—O15	121.1 (5)	C4—C3—H3C	108.9
O20—B10—O15	116.0 (5)	N3—C3—H3C	108.9
C1—N1—Co1	110.0 (4)	C4—C3—H3D	108.9
C1—N1—H1A	109.7	N3—C3—H3D	108.9
Co1—N1—H1A	109.7	H3C—C3—H3D	107.7
C1—N1—H1B	109.7	N4—C4—C3	115.5 (7)
Co1—N1—H1B	109.7	N4—C4—H4C	108.4
H1A—N1—H1B	108.2	C3—C4—H4C	108.4
C2—N2—Co1	109.2 (4)	N4—C4—H4D	108.4
C2—N2—H2A	109.8	C3—C4—H4D	108.4
Co1—N2—H2A	109.8	H4C—C4—H4D	107.5
C2—N2—H2B	109.8	N5—C5—C6	112.4 (7)
Co1—N2—H2B	109.8	N5—C5—H5C	109.1
H2A—N2—H2B	108.3	C6—C5—H5C	109.1
C3—N3—Co1	110.7 (5)	N5—C5—H5D	109.1
C3—N3—H3A	109.5	C6—C5—H5D	109.1
Co1—N3—H3A	109.5	H5C—C5—H5D	107.9
C3—N3—H3B	109.5	N6—C6—C5	114.1 (7)
Co1—N3—H3B	109.5	N6—C6—H6C	108.7
H3A—N3—H3B	108.1	C5—C6—H6C	108.7
C4—N4—Co1	110.7 (5)	N6—C6—H6D	108.7
C4—N4—H4A	109.5	C5—C6—H6D	108.7
Co1—N4—H4A	109.5	H6C—C6—H6D	107.6
C4—N4—H4B	109.5
N2—Co1—N1—C1	−14.4 (5)	O9—B4—O5—B5	168.5 (6)
N6—Co1—N1—C1	−108.9 (5)	O6—B5—O5—B4	10.5 (9)
N3—Co1—N1—C1	82.5 (5)	O10—B5—O5—B4	−168.4 (6)
N4—Co1—N1—C1	160.5 (5)	O10—B5—O6—B1	−177.1 (5)
N6—Co1—N2—C2	86.2 (6)	O5—B5—O6—B1	4.2 (8)
N3—Co1—N2—C2	−101.2 (6)	O4—B1—O6—B5	−15.5 (7)
N1—Co1—N2—C2	−10.5 (6)	O3—B1—O6—B5	−135.4 (5)
N5—Co1—N2—C2	165.1 (6)	O1—B1—O6—B5	105.3 (6)
N2—Co1—N3—C3	−175.7 (5)	O17—B7—O11—B6	178.1 (5)
N6—Co1—N3—C3	−25.9 (11)	O12—B7—O11—B6	−3.0 (9)
N1—Co1—N3—C3	104.1 (5)	O14—B6—O11—B7	126.0 (5)
N5—Co1—N3—C3	−81.2 (5)	O13—B6—O11—B7	5.6 (7)
N4—Co1—N3—C3	12.2 (5)	O16—B6—O11—B7	−113.4 (5)
N6—Co1—N4—C4	178.9 (6)	O13—B8—O12—B7	3.4 (9)
N3—Co1—N4—C4	8.1 (6)	O18—B8—O12—B7	−179.2 (6)
N1—Co1—N4—C4	−83.4 (6)	O11—B7—O12—B8	−1.8 (9)
N5—Co1—N4—C4	100.4 (6)	O17—B7—O12—B8	177.1 (6)
N2—Co1—N5—C5	−113.7 (5)	O12—B8—O13—B6	−0.3 (9)
N6—Co1—N5—C5	−18.7 (5)	O18—B8—O13—B6	−177.6 (5)
N3—Co1—N5—C5	148.9 (5)	O11—B6—O13—B8	−3.9 (7)
N4—Co1—N5—C5	70.8 (5)	O14—B6—O13—B8	−124.4 (5)
N2—Co1—N6—C6	90.4 (6)	O16—B6—O13—B8	116.4 (5)
N3—Co1—N6—C6	−59.5 (11)	O19—B9—O14—B6	−179.4 (6)
N1—Co1—N6—C6	171.1 (6)	O15—B9—O14—B6	0.6 (10)
N5—Co1—N6—C6	−2.6 (6)	O11—B6—O14—B9	121.2 (6)
N4—Co1—N6—C6	−96.6 (6)	O13—B6—O14—B9	−116.7 (6)
O7—B2—O1—B1	177.7 (5)	O16—B6—O14—B9	0.9 (8)
O2—B2—O1—B1	0.8 (9)	O16—B10—O15—B9	4.1 (9)
O4—B1—O1—B2	−112.9 (5)	O20—B10—O15—B9	−174.0 (6)
O6—B1—O1—B2	125.2 (5)	O14—B9—O15—B10	−3.2 (10)
O3—B1—O1—B2	7.0 (7)	O19—B9—O15—B10	176.8 (6)
O7—B2—O2—B3	177.7 (6)	O20—B10—O16—B6	175.5 (5)
O1—B2—O2—B3	−5.1 (9)	O15—B10—O16—B6	−2.6 (9)
O3—B3—O2—B2	0.5 (10)	O11—B6—O16—B10	−119.9 (6)
O8—B3—O2—B2	−179.3 (6)	O14—B6—O16—B10	0.1 (8)
O8—B3—O3—B1	−171.5 (6)	O13—B6—O16—B10	118.6 (5)
O2—B3—O3—B1	8.8 (10)	Co1—N1—C1—C2	36.8 (9)
O4—B1—O3—B3	108.3 (6)	Co1—N2—C2—C1	34.8 (9)
O6—B1—O3—B3	−130.6 (6)	N1—C1—C2—N2	−48.5 (11)
O1—B1—O3—B3	−11.8 (8)	Co1—N3—C3—C4	−31.1 (9)
O5—B4—O4—B1	−0.7 (9)	Co1—N4—C4—C3	−28.2 (10)
O9—B4—O4—B1	178.5 (5)	N3—C3—C4—N4	40.7 (11)
O6—B1—O4—B4	13.8 (7)	Co1—N5—C5—C6	37.6 (8)
O3—B1—O4—B4	132.9 (5)	Co1—N6—C6—C5	23.9 (9)
O1—B1—O4—B4	−106.7 (6)	N5—C5—C6—N6	−41.8 (10)
O4—B4—O5—B5	−12.3 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O15i	0.90	2.36	3.188 (7)	154
N1—H1A···O19i	0.90	2.64	3.425 (7)	147
N1—H1B···O11ii	0.90	2.38	3.276 (7)	174
N2—H2A···O8iii	0.90	2.23	3.089 (7)	159
N2—H2B···O21iv	0.90	2.18	3.030 (10)	157
N3—H3A···O2iii	0.90	2.23	3.074 (7)	157
N4—H4A···O20i	0.90	2.49	3.199 (7)	136
N5—H5B···O7iii	0.90	2.34	3.085 (7)	140
N6—H6A···O20i	0.90	2.42	3.302 (7)	168
N6—H6B···O22iv	0.90	2.38	3.235 (12)	158
O7—H7···O16v	0.82	1.84	2.647 (5)	170
O8—H8···O3iii	0.82	1.87	2.687 (5)	170
O10—H10···O13vi	0.82	1.94	2.753 (6)	172
O18—H18···O6vii	0.82	1.88	2.687 (6)	170
O19—H19···O14i	0.82	1.89	2.691 (5)	164
O20—H20···O1viii	0.82	1.91	2.725 (5)	170
O22—H3···O19ix	0.85	2.45	2.993 (11)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O15i	0.90	2.36	3.188 (7)	154
N1—H1A⋯O19i	0.90	2.64	3.425 (7)	147
N1—H1B⋯O11ii	0.90	2.38	3.276 (7)	174
N2—H2A⋯O8iii	0.90	2.23	3.089 (7)	159
N2—H2B⋯O21iv	0.90	2.18	3.030 (10)	157
N3—H3A⋯O2iii	0.90	2.23	3.074 (7)	157
N4—H4A⋯O20i	0.90	2.49	3.199 (7)	136
N5—H5B⋯O7iii	0.90	2.34	3.085 (7)	140
N6—H6A⋯O20i	0.90	2.42	3.302 (7)	168
N6—H6B⋯O22iv	0.90	2.38	3.235 (12)	158
O7—H7⋯O16v	0.82	1.84	2.647 (5)	170
O8—H8⋯O3iii	0.82	1.87	2.687 (5)	170
O10—H10⋯O13vi	0.82	1.94	2.753 (6)	172
O18—H18⋯O6vii	0.82	1.88	2.687 (6)	170
O19—H19⋯O14i	0.82	1.89	2.691 (5)	164
O20—H20⋯O1viii	0.82	1.91	2.725 (5)	170
O22—H3⋯O19ix	0.85	2.45	2.993 (11)	122

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) .