A new two-dimensional Co^II coordination polymer based on bis­[4-(2-methyl-1H-imidazol-1-yl)phen­yl] ether and biphenyl-4,4′-diyldi­carb­oxy­lic acid: synthesis, crystal structure and photocatalytic degradation activity

A novel two-dimensional Co^II coordination framework, namely poly[(μ₂-bi­phenyl-4,4′-diyldi­carboxyl­ato-κ²O⁴:O^4′){μ₂-bis­[4-(2-methyl-1H-imidazol-1-yl)phen­yl] ether-κ²N³:N^3′}cobalt(II)], [Co(C₁₄H₈O₄)(C₂₀H₁₈N₄O)]_n, has been pre­pared and characterized by IR, elemental analysis, thermal analysis and single-crystal X-ray diffraction. The crystal structure reveals that the compound has an achiral two-dimensional layered structure based on opposite-handed helical chains. In addition, it exhibits significant photocatalytic degradation activity for the degradation of methyl­ene blue.

Computing details

Data collection: APEX3 (Bruker, 2018); cell refinement: SAINT (Bruker, 2018); data reduction: SAINT (Bruker, 2018); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b).

Poly[(µ₂-biphenyl-4,4'-diyldicarboxylato-κ²O⁴:O^4'){µ₂-bis[4-(2-methyl-1H-imidazol-1-yl)phenyl] ether-κ²N³:N^3'}cobalt(II)]

Crystal data

[Co(C14H8O4)(C20H18N4O)]	F(000) = 1300
Mr = 629.52	Dx = 1.511 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.844 (5) Å	Cell parameters from 9179 reflections
b = 20.558 (13) Å	θ = 2.8–27.4°
c = 17.168 (12) Å	µ = 0.67 mm^−1
β = 90.93 (2)°	T = 293 K
V = 2768 (3) Å^3	Block, red
Z = 4	0.21 × 0.20 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer	4590 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
φ and ω scans	θmax = 26.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→9
Tmin = 0.868, Tmax = 0.880	k = −25→25
62557 measured reflections	l = −21→21
5441 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.0413P)^2 + 2.5455P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
5441 reflections	Δρmax = 0.35 e Å^−3
398 parameters	Δρmin = −0.34 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.2125 (3)	0.54374 (14)	0.13562 (16)	0.0398 (6)
C2	0.0676 (3)	0.49695 (13)	0.12551 (15)	0.0365 (6)
C3	0.1010 (3)	0.43123 (13)	0.13065 (18)	0.0433 (7)
H3	0.213431	0.416954	0.133507	0.052*
C4	−0.0292 (3)	0.38642 (13)	0.13164 (18)	0.0441 (7)
H4	−0.003422	0.342398	0.136006	0.053*
C5	−0.1995 (3)	0.40599 (12)	0.12619 (15)	0.0346 (6)
C6	−0.2321 (3)	0.47184 (13)	0.11803 (18)	0.0437 (7)
H6	−0.344126	0.486120	0.112451	0.052*
C7	−0.1007 (3)	0.51678 (13)	0.11803 (18)	0.0449 (7)
H7	−0.125686	0.560812	0.112945	0.054*
C8	−0.3367 (3)	0.35800 (12)	0.13618 (15)	0.0339 (5)
C9	−0.3283 (3)	0.29693 (12)	0.10134 (16)	0.0379 (6)
H9	−0.240805	0.287721	0.067130	0.046*
C10	−0.4493 (3)	0.24964 (13)	0.11718 (15)	0.0376 (6)
H10	−0.443298	0.209422	0.092587	0.045*
C11	−0.5796 (3)	0.26164 (12)	0.16937 (14)	0.0310 (5)
C12	−0.5899 (3)	0.32294 (12)	0.20226 (15)	0.0362 (6)
H12	−0.677643	0.332334	0.236271	0.043*
C13	−0.4718 (3)	0.37022 (12)	0.18523 (16)	0.0376 (6)
H13	−0.482850	0.411342	0.207152	0.045*
C14	−0.6973 (3)	0.20765 (12)	0.19257 (14)	0.0297 (5)
C15	0.3919 (3)	0.52426 (12)	0.31731 (15)	0.0356 (6)
H15	0.273567	0.523110	0.312879	0.043*
C16	0.4874 (3)	0.48072 (12)	0.35587 (15)	0.0350 (6)
H16	0.449038	0.444493	0.382874	0.042*
C17	0.6535 (3)	0.55580 (11)	0.30482 (13)	0.0258 (5)
C18	0.8057 (3)	0.59543 (13)	0.28862 (17)	0.0391 (6)
H18A	0.905444	0.573782	0.308797	0.059*	0.5
H18B	0.815745	0.601126	0.233386	0.059*	0.5
H18C	0.794877	0.637164	0.313136	0.059*	0.5
H18D	0.771933	0.634266	0.261416	0.059*	0.5
H18E	0.861632	0.606922	0.336826	0.059*	0.5
H18F	0.882501	0.570884	0.257077	0.059*	0.5
C19	0.7959 (3)	0.46777 (11)	0.38447 (14)	0.0277 (5)
C20	0.7880 (3)	0.45446 (12)	0.46325 (14)	0.0317 (5)
H20	0.693444	0.467523	0.491261	0.038*
C21	0.9188 (3)	0.42211 (11)	0.50026 (14)	0.0315 (5)
H21	0.912481	0.412424	0.553050	0.038*
C22	1.0601 (3)	0.40401 (11)	0.45851 (14)	0.0276 (5)
C23	1.0696 (3)	0.41630 (12)	0.37971 (14)	0.0309 (5)
H23	1.164835	0.403525	0.352027	0.037*
C24	0.9348 (3)	0.44805 (12)	0.34211 (14)	0.0312 (5)
H24	0.938285	0.455925	0.288822	0.037*
C25	1.3192 (3)	0.33872 (11)	0.47805 (13)	0.0269 (5)
C26	1.3006 (3)	0.29374 (12)	0.41930 (15)	0.0335 (5)
H26	1.198461	0.290753	0.391232	0.040*
C27	1.4352 (3)	0.25298 (12)	0.40235 (15)	0.0346 (6)
H27	1.424097	0.222507	0.362556	0.042*
C28	1.5858 (3)	0.25753 (11)	0.44441 (13)	0.0281 (5)
C29	1.6027 (3)	0.30194 (12)	0.50412 (14)	0.0327 (5)
H29	1.704021	0.304463	0.532879	0.039*
C30	1.4685 (3)	0.34265 (12)	0.52101 (14)	0.0324 (5)
H30	1.478838	0.372675	0.561324	0.039*
C31	1.7821 (4)	0.16495 (14)	0.47592 (16)	0.0443 (7)
H31	1.738488	0.153352	0.524006	0.053*
C32	1.9117 (3)	0.13672 (13)	0.43940 (15)	0.0388 (6)
H32	1.973652	0.101294	0.458162	0.047*
C33	1.8258 (3)	0.21553 (11)	0.36505 (13)	0.0275 (5)
C34	1.8114 (4)	0.26441 (14)	0.30243 (17)	0.0459 (7)
H34A	1.706577	0.257954	0.273835	0.069*
H34B	1.905744	0.259876	0.267919	0.069*
H34C	1.812539	0.307219	0.324769	0.069*
Co1	0.38825 (4)	0.63716 (2)	0.20989 (2)	0.02535 (10)
N1	0.4949 (2)	0.57120 (9)	0.28504 (11)	0.0283 (4)
N2	0.6541 (2)	0.50020 (9)	0.34763 (11)	0.0279 (4)
N3	1.7257 (2)	0.21484 (10)	0.42804 (11)	0.0302 (4)
N4	1.9398 (2)	0.16780 (9)	0.37013 (11)	0.0277 (4)
O1	0.1786 (2)	0.59997 (9)	0.16236 (12)	0.0455 (5)
O2	0.3594 (3)	0.52567 (11)	0.12400 (15)	0.0620 (6)
O3	−0.8075 (2)	0.22033 (8)	0.24528 (10)	0.0339 (4)
O4	−0.6800 (2)	0.15338 (8)	0.16399 (11)	0.0406 (4)
O5	1.1910 (2)	0.37890 (9)	0.50455 (10)	0.0386 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0343 (14)	0.0425 (16)	0.0426 (15)	−0.0096 (12)	−0.0003 (11)	0.0032 (12)
C2	0.0324 (13)	0.0370 (14)	0.0402 (14)	−0.0078 (11)	0.0023 (11)	−0.0020 (11)
C3	0.0267 (13)	0.0417 (15)	0.0617 (18)	−0.0025 (11)	0.0038 (12)	−0.0071 (13)
C4	0.0354 (14)	0.0299 (13)	0.0673 (19)	−0.0018 (11)	0.0070 (13)	−0.0058 (13)
C5	0.0329 (13)	0.0316 (13)	0.0395 (14)	−0.0032 (10)	0.0033 (11)	−0.0041 (11)
C6	0.0276 (13)	0.0377 (15)	0.0658 (19)	−0.0030 (11)	−0.0024 (12)	0.0033 (13)
C7	0.0392 (15)	0.0313 (14)	0.0642 (19)	−0.0031 (12)	−0.0028 (13)	0.0024 (13)
C8	0.0291 (12)	0.0337 (13)	0.0388 (14)	−0.0032 (10)	−0.0016 (10)	−0.0010 (11)
C9	0.0343 (14)	0.0362 (14)	0.0436 (15)	−0.0046 (11)	0.0097 (11)	−0.0077 (11)
C10	0.0378 (14)	0.0340 (14)	0.0412 (14)	−0.0058 (11)	0.0065 (11)	−0.0093 (11)
C11	0.0279 (12)	0.0315 (13)	0.0334 (13)	−0.0025 (10)	−0.0015 (10)	0.0008 (10)
C12	0.0307 (13)	0.0353 (14)	0.0428 (15)	0.0005 (11)	0.0077 (11)	−0.0021 (11)
C13	0.0354 (14)	0.0294 (13)	0.0481 (15)	0.0010 (11)	0.0042 (11)	−0.0080 (11)
C14	0.0259 (12)	0.0333 (13)	0.0298 (12)	−0.0056 (10)	−0.0038 (10)	0.0032 (10)
C15	0.0215 (12)	0.0386 (14)	0.0467 (15)	0.0006 (10)	0.0022 (10)	0.0106 (12)
C16	0.0262 (12)	0.0332 (13)	0.0456 (15)	−0.0021 (10)	0.0039 (11)	0.0114 (11)
C17	0.0240 (11)	0.0256 (12)	0.0277 (12)	0.0030 (9)	0.0015 (9)	0.0005 (9)
C18	0.0289 (13)	0.0369 (14)	0.0514 (16)	−0.0027 (11)	−0.0007 (11)	0.0114 (12)
C19	0.0240 (11)	0.0248 (12)	0.0344 (13)	0.0038 (9)	−0.0010 (9)	0.0047 (9)
C20	0.0248 (12)	0.0349 (13)	0.0356 (13)	0.0061 (10)	0.0075 (10)	0.0032 (10)
C21	0.0330 (13)	0.0319 (13)	0.0296 (13)	0.0058 (10)	0.0050 (10)	0.0053 (10)
C22	0.0253 (11)	0.0236 (11)	0.0338 (13)	0.0060 (9)	−0.0023 (9)	0.0016 (9)
C23	0.0246 (12)	0.0342 (13)	0.0341 (13)	0.0091 (10)	0.0058 (10)	0.0010 (10)
C24	0.0323 (13)	0.0330 (13)	0.0283 (12)	0.0042 (10)	0.0025 (10)	0.0055 (10)
C25	0.0252 (11)	0.0280 (12)	0.0277 (12)	0.0075 (9)	0.0029 (9)	0.0047 (9)
C26	0.0254 (12)	0.0368 (14)	0.0381 (14)	0.0045 (10)	−0.0060 (10)	−0.0040 (11)
C27	0.0340 (13)	0.0344 (13)	0.0352 (13)	0.0050 (11)	−0.0053 (10)	−0.0116 (11)
C28	0.0252 (11)	0.0300 (12)	0.0290 (12)	0.0067 (9)	0.0024 (9)	−0.0010 (10)
C29	0.0253 (12)	0.0396 (14)	0.0331 (13)	0.0047 (10)	−0.0049 (10)	−0.0053 (11)
C30	0.0330 (13)	0.0328 (13)	0.0313 (13)	0.0046 (10)	−0.0015 (10)	−0.0091 (10)
C31	0.0497 (17)	0.0495 (16)	0.0340 (14)	0.0161 (13)	0.0098 (12)	0.0099 (12)
C32	0.0427 (15)	0.0376 (14)	0.0362 (14)	0.0155 (12)	0.0039 (11)	0.0066 (11)
C33	0.0254 (11)	0.0286 (12)	0.0285 (12)	0.0023 (9)	−0.0020 (9)	−0.0029 (9)
C34	0.0455 (16)	0.0460 (16)	0.0467 (16)	0.0153 (13)	0.0109 (13)	0.0131 (13)
Co1	0.02015 (16)	0.02281 (17)	0.03310 (18)	−0.00055 (12)	0.00090 (12)	0.00363 (13)
N1	0.0229 (10)	0.0266 (10)	0.0353 (11)	0.0032 (8)	0.0017 (8)	0.0050 (8)
N2	0.0224 (9)	0.0273 (10)	0.0341 (11)	0.0024 (8)	0.0017 (8)	0.0061 (8)
N3	0.0282 (10)	0.0325 (11)	0.0300 (11)	0.0098 (8)	0.0018 (8)	−0.0016 (8)
N4	0.0251 (10)	0.0267 (10)	0.0313 (10)	0.0043 (8)	0.0009 (8)	−0.0032 (8)
O1	0.0419 (11)	0.0362 (11)	0.0583 (12)	−0.0104 (8)	−0.0090 (9)	−0.0046 (9)
O2	0.0323 (11)	0.0580 (13)	0.0960 (18)	−0.0087 (10)	0.0064 (11)	0.0024 (12)
O3	0.0320 (9)	0.0309 (9)	0.0391 (10)	−0.0038 (7)	0.0079 (8)	0.0009 (7)
O4	0.0391 (10)	0.0329 (10)	0.0500 (11)	−0.0087 (8)	0.0068 (8)	−0.0061 (8)
O5	0.0367 (10)	0.0485 (11)	0.0307 (9)	0.0233 (8)	−0.0024 (7)	−0.0030 (8)

Geometric parameters (Å, º)

C1—O2	1.231 (3)	C18—H18F	0.9600
C1—O1	1.273 (3)	C19—C24	1.381 (3)
C1—C2	1.496 (4)	C19—C20	1.382 (3)
C2—C3	1.379 (4)	C19—N2	1.435 (3)
C2—C7	1.386 (4)	C20—C21	1.370 (3)
C3—C4	1.376 (4)	C20—H20	0.9300
C3—H3	0.9300	C21—C22	1.381 (3)
C4—C5	1.397 (4)	C21—H21	0.9300
C4—H4	0.9300	C22—C23	1.379 (3)
C5—C6	1.384 (4)	C22—O5	1.385 (3)
C5—C8	1.472 (3)	C23—C24	1.392 (3)
C6—C7	1.384 (4)	C23—H23	0.9300
C6—H6	0.9300	C24—H24	0.9300
C7—H7	0.9300	C25—C26	1.374 (3)
C8—C13	1.387 (4)	C25—C30	1.376 (3)
C8—C9	1.393 (4)	C25—O5	1.384 (3)
C9—C10	1.389 (4)	C26—C27	1.383 (3)
C9—H9	0.9300	C26—H26	0.9300
C10—C11	1.392 (4)	C27—C28	1.378 (3)
C10—H10	0.9300	C27—H27	0.9300
C11—C12	1.384 (4)	C28—C29	1.377 (3)
C11—C14	1.502 (3)	C28—N3	1.436 (3)
C12—C13	1.378 (4)	C29—C30	1.380 (3)
C12—H12	0.9300	C29—H29	0.9300
C13—H13	0.9300	C30—H30	0.9300
C14—O4	1.227 (3)	C31—C32	1.336 (4)
C14—O3	1.288 (3)	C31—N3	1.383 (3)
C15—C16	1.336 (3)	C31—H31	0.9300
C15—N1	1.381 (3)	C32—N4	1.371 (3)
C15—H15	0.9300	C32—H32	0.9300
C16—N2	1.377 (3)	C33—N4	1.330 (3)
C16—H16	0.9300	C33—N3	1.347 (3)
C17—N1	1.323 (3)	C33—C34	1.475 (4)
C17—N2	1.359 (3)	C34—H34A	0.9600
C17—C18	1.476 (3)	C34—H34B	0.9600
C18—H18A	0.9600	C34—H34C	0.9600
C18—H18B	0.9600	Co1—O1	1.977 (2)
C18—H18C	0.9600	Co1—O3^i	1.9831 (19)
C18—H18D	0.9600	Co1—N4^ii	2.040 (2)
C18—H18E	0.9600	Co1—N1	2.042 (2)
O2—C1—O1	122.3 (2)	C20—C21—C22	119.4 (2)
O2—C1—C2	119.9 (3)	C20—C21—H21	120.3
O1—C1—C2	117.6 (2)	C22—C21—H21	120.3
C3—C2—C7	118.3 (2)	C23—C22—C21	121.1 (2)
C3—C2—C1	118.7 (2)	C23—C22—O5	125.2 (2)
C7—C2—C1	122.8 (2)	C21—C22—O5	113.4 (2)
C4—C3—C2	121.1 (3)	C22—C23—C24	119.2 (2)
C4—C3—H3	119.4	C22—C23—H23	120.4
C2—C3—H3	119.4	C24—C23—H23	120.4
C3—C4—C5	121.0 (3)	C19—C24—C23	119.6 (2)
C3—C4—H4	119.5	C19—C24—H24	120.2
C5—C4—H4	119.5	C23—C24—H24	120.2
C6—C5—C4	117.6 (2)	C26—C25—C30	120.8 (2)
C6—C5—C8	122.2 (2)	C26—C25—O5	125.0 (2)
C4—C5—C8	119.9 (2)	C30—C25—O5	113.9 (2)
C7—C6—C5	121.1 (3)	C25—C26—C27	119.3 (2)
C7—C6—H6	119.4	C25—C26—H26	120.3
C5—C6—H6	119.4	C27—C26—H26	120.3
C6—C7—C2	120.8 (3)	C28—C27—C26	120.0 (2)
C6—C7—H7	119.6	C28—C27—H27	120.0
C2—C7—H7	119.6	C26—C27—H27	120.0
C13—C8—C9	117.8 (2)	C29—C28—C27	120.4 (2)
C13—C8—C5	121.1 (2)	C29—C28—N3	119.1 (2)
C9—C8—C5	121.0 (2)	C27—C28—N3	120.5 (2)
C10—C9—C8	120.6 (2)	C28—C29—C30	119.6 (2)
C10—C9—H9	119.7	C28—C29—H29	120.2
C8—C9—H9	119.7	C30—C29—H29	120.2
C9—C10—C11	120.9 (2)	C25—C30—C29	119.8 (2)
C9—C10—H10	119.6	C25—C30—H30	120.1
C11—C10—H10	119.6	C29—C30—H30	120.1
C12—C11—C10	118.2 (2)	C32—C31—N3	106.4 (2)
C12—C11—C14	121.6 (2)	C32—C31—H31	126.8
C10—C11—C14	120.0 (2)	N3—C31—H31	126.8
C13—C12—C11	120.8 (2)	C31—C32—N4	109.8 (2)
C13—C12—H12	119.6	C31—C32—H32	125.1
C11—C12—H12	119.6	N4—C32—H32	125.1
C12—C13—C8	121.6 (2)	N4—C33—N3	109.9 (2)
C12—C13—H13	119.2	N4—C33—C34	126.4 (2)
C8—C13—H13	119.2	N3—C33—C34	123.6 (2)
O4—C14—O3	123.0 (2)	C33—C34—H34A	109.5
O4—C14—C11	119.6 (2)	C33—C34—H34B	109.5
O3—C14—C11	117.3 (2)	H34A—C34—H34B	109.5
C16—C15—N1	109.9 (2)	C33—C34—H34C	109.5
C16—C15—H15	125.1	H34A—C34—H34C	109.5
N1—C15—H15	125.1	H34B—C34—H34C	109.5
C15—C16—N2	106.3 (2)	O1—Co1—O3^i	102.99 (8)
C15—C16—H16	126.9	O1—Co1—N4^ii	113.31 (9)
N2—C16—H16	126.9	O3^i—Co1—N4^ii	102.36 (8)
N1—C17—N2	109.59 (19)	O1—Co1—N1	109.47 (9)
N1—C17—C18	125.4 (2)	O3^i—Co1—N1	117.23 (9)
N2—C17—C18	124.8 (2)	N4^ii—Co1—N1	111.23 (9)
C17—C18—H18A	109.5	C17—N1—C15	106.49 (19)
C17—C18—H18B	109.5	C17—N1—Co1	134.04 (16)
H18A—C18—H18B	109.5	C15—N1—Co1	118.78 (16)
C17—C18—H18C	109.5	C17—N2—C16	107.76 (19)
H18A—C18—H18C	109.5	C17—N2—C19	128.70 (19)
H18B—C18—H18C	109.5	C16—N2—C19	123.38 (19)
H18D—C18—H18E	109.5	C33—N3—C31	107.5 (2)
H18D—C18—H18F	109.5	C33—N3—C28	127.4 (2)
H18E—C18—H18F	109.5	C31—N3—C28	125.1 (2)
C24—C19—C20	120.4 (2)	C33—N4—C32	106.45 (19)
C24—C19—N2	121.1 (2)	C33—N4—Co1^iii	129.43 (16)
C20—C19—N2	118.5 (2)	C32—N4—Co1^iii	123.89 (16)
C21—C20—C19	120.3 (2)	C1—O1—Co1	108.85 (17)
C21—C20—H20	119.8	C14—O3—Co1^iv	108.69 (15)
C19—C20—H20	119.8	C25—O5—C22	124.78 (19)
O2—C1—C2—C3	22.7 (4)	C26—C27—C28—N3	179.1 (2)
O1—C1—C2—C3	−151.7 (3)	C27—C28—C29—C30	−0.9 (4)
O2—C1—C2—C7	−163.2 (3)	N3—C28—C29—C30	−179.2 (2)
O1—C1—C2—C7	22.4 (4)	C26—C25—C30—C29	1.3 (4)
C7—C2—C3—C4	−2.7 (4)	O5—C25—C30—C29	175.6 (2)
C1—C2—C3—C4	171.8 (3)	C28—C29—C30—C25	−0.2 (4)
C2—C3—C4—C5	1.0 (5)	N3—C31—C32—N4	0.6 (3)
C3—C4—C5—C6	1.4 (4)	N2—C17—N1—C15	0.8 (3)
C3—C4—C5—C8	−173.1 (3)	C18—C17—N1—C15	−174.6 (2)
C4—C5—C6—C7	−2.2 (4)	N2—C17—N1—Co1	−169.21 (16)
C8—C5—C6—C7	172.2 (3)	C18—C17—N1—Co1	15.4 (4)
C5—C6—C7—C2	0.6 (5)	C16—C15—N1—C17	−0.3 (3)
C3—C2—C7—C6	1.9 (4)	C16—C15—N1—Co1	171.51 (18)
C1—C2—C7—C6	−172.3 (3)	N1—C17—N2—C16	−1.0 (3)
C6—C5—C8—C13	−42.7 (4)	C18—C17—N2—C16	174.4 (2)
C4—C5—C8—C13	131.6 (3)	N1—C17—N2—C19	−176.5 (2)
C6—C5—C8—C9	142.3 (3)	C18—C17—N2—C19	−1.0 (4)
C4—C5—C8—C9	−43.4 (4)	C15—C16—N2—C17	0.8 (3)
C13—C8—C9—C10	−1.7 (4)	C15—C16—N2—C19	176.5 (2)
C5—C8—C9—C10	173.6 (2)	C24—C19—N2—C17	−56.9 (3)
C8—C9—C10—C11	−1.3 (4)	C20—C19—N2—C17	125.4 (3)
C9—C10—C11—C12	3.0 (4)	C24—C19—N2—C16	128.3 (3)
C9—C10—C11—C14	−173.1 (2)	C20—C19—N2—C16	−49.4 (3)
C10—C11—C12—C13	−1.6 (4)	N4—C33—N3—C31	1.3 (3)
C14—C11—C12—C13	174.4 (2)	C34—C33—N3—C31	−176.5 (3)
C11—C12—C13—C8	−1.4 (4)	N4—C33—N3—C28	−179.0 (2)
C9—C8—C13—C12	3.0 (4)	C34—C33—N3—C28	3.2 (4)
C5—C8—C13—C12	−172.2 (2)	C32—C31—N3—C33	−1.1 (3)
C12—C11—C14—O4	−177.4 (2)	C32—C31—N3—C28	179.2 (2)
C10—C11—C14—O4	−1.5 (4)	C29—C28—N3—C33	−110.7 (3)
C12—C11—C14—O3	−0.9 (3)	C27—C28—N3—C33	71.0 (3)
C10—C11—C14—O3	175.1 (2)	C29—C28—N3—C31	69.0 (3)
N1—C15—C16—N2	−0.3 (3)	C27—C28—N3—C31	−109.3 (3)
C24—C19—C20—C21	0.7 (4)	N3—C33—N4—C32	−0.9 (3)
N2—C19—C20—C21	178.4 (2)	C34—C33—N4—C32	176.8 (3)
C19—C20—C21—C22	1.2 (4)	N3—C33—N4—Co1^iii	173.54 (15)
C20—C21—C22—C23	−1.9 (4)	C34—C33—N4—Co1^iii	−8.7 (4)
C20—C21—C22—O5	172.6 (2)	C31—C32—N4—C33	0.2 (3)
C21—C22—C23—C24	0.6 (4)	C31—C32—N4—Co1^iii	−174.66 (19)
O5—C22—C23—C24	−173.2 (2)	O2—C1—O1—Co1	−17.4 (3)
C20—C19—C24—C23	−1.9 (4)	C2—C1—O1—Co1	156.87 (19)
N2—C19—C24—C23	−179.5 (2)	O4—C14—O3—Co1^iv	15.6 (3)
C22—C23—C24—C19	1.3 (4)	C11—C14—O3—Co1^iv	−160.79 (16)
C30—C25—C26—C27	−1.4 (4)	C26—C25—O5—C22	−33.0 (4)
O5—C25—C26—C27	−175.0 (2)	C30—C25—O5—C22	153.0 (2)
C25—C26—C27—C28	0.3 (4)	C23—C22—O5—C25	−27.9 (4)
C26—C27—C28—C29	0.9 (4)	C21—C22—O5—C25	157.9 (2)

Symmetry codes: (i) −x−1/2, y+1/2, −z+1/2; (ii) −x+5/2, y+1/2, −z+1/2; (iii) −x+5/2, y−1/2, −z+1/2; (iv) −x−1/2, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O4^v	0.93	2.46	3.314 (3)	154
C29—H29···O4^vi	0.93	2.57	3.336 (4)	141
C32—H32···O2^iii	0.93	2.49	3.112 (4)	125
C34—H34B···O3^vii	0.96	2.43	3.289 (4)	149
C21—H21···O4^v	0.93	2.46	3.314 (3)	154
C29—H29···O4^vi	0.93	2.57	3.336 (4)	141
C32—H32···O2^iii	0.93	2.49	3.112 (4)	125
C34—H34B···O3^vii	0.96	2.43	3.289 (4)	149

Symmetry codes: (iii) −x+5/2, y−1/2, −z+1/2; (v) x+3/2, −y+1/2, z+1/2; (vi) x+5/2, −y+1/2, z+1/2; (vii) x+3, y, z.