catena-Poly[[[aqua-chlorido-manganese(II)]-bis-[μ-1,1'-(oxydi-p-phenyl-ene)di-1H-imidazole-κN:N]] chloride dimethyl-formamide mono-solvate monohydrate].

The title coordination polymer, {[MnCl(C(18)H(14)N(4)O)(2)(H(2)O)]Cl·C(3)H(7)NO·H(2)O}(n), obtained by the solvothermal reaction of BIDPE and manganese(II) salt in H(2)O/DMF (DMF is dimethyl-formamide), is composed of a chain of [Mn(2)(BIDPE)(2)] [BIDPE is 1,1'-(oxydi-p-phenyl-ene)di-1H-imidazole] metallocyclic rings that exhibit inversion symmetry. The coordination about the Mn(II) ions is distorted octahedral with a MnClN(4)O coordination set. In the crystal, the polymeric chains are linked by O-H⋯Cl hydrogen bonds, forming a two-dimensional network parallel to (100). A number of C-H⋯Cl and C-H⋯O inter-actions are also present.

Related literature

For potential applications of metal-organic frameworks, see: Feng et al. (2009 ▶); Bauer et al. (2007 ▶); Kumagai et al. (2002 ▶); Bi et al. (2009 ▶); Reddy et al. (2010 ▶); Cho et al. (2006 ▶); Maji et al. (2005 ▶); Zhang et al. (2009 ▶). For the synthesis of the 4,4′-bis­(imidazol-1-yl) diphenyl ether (BIDPE) ligand, see: Hu et al. (2010 ▶).

Experimental

Crystal data

[MnCl(C18H14N4O)2(H2O)]Cl·C3H7NO·H2O

M = 839.63

Triclinic,

a = 12.6167 (14) Å

b = 12.6183 (14) Å

c = 13.5274 (15) Å

α = 74.801 (2)°

β = 69.388 (2)°

γ = 85.582 (2)°

V = 1944.9 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.53 mm−1

T = 273 K

0.32 × 0.30 × 0.29 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.843, T max = 0.857

10456 measured reflections

7427 independent reflections

5475 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.133

S = 1.08

7427 reflections

517 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.55 e Å−3

Δρmin = −0.42 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 global, I. DOI: 10.1107/S1600536810054383/su2233sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810054383/su2233Isup2.hkl

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

[MnCl(C18H14N4O)2(H2O)]Cl·C3H7NO·H2O	Z = 2
Mr = 839.63	F(000) = 870
Triclinic, P1	Dx = 1.434 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.6167 (14) Å	Cell parameters from 4541 reflections
b = 12.6183 (14) Å	θ = 2.3–27.4°
c = 13.5274 (15) Å	µ = 0.53 mm−1
α = 74.801 (2)°	T = 273 K
β = 69.388 (2)°	Block, colourless
γ = 85.582 (2)°	0.32 × 0.30 × 0.29 mm
V = 1944.9 (4) Å3

Bruker SMART CCD area-detector diffractometer	7427 independent reflections
Radiation source: fine-focus sealed tube	5475 reflections with I > 2σ(I)
graphite	Rint = 0.047
phi and ω scans	θmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −15→14
Tmin = 0.843, Tmax = 0.857	k = −12→15
10456 measured reflections	l = −16→16

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0723P)2] where P = (Fo2 + 2Fc2)/3
7427 reflections	(Δ/σ)max < 0.001
517 parameters	Δρmax = 0.55 e Å−3
6 restraints	Δρmin = −0.42 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
Mn1	0.77799 (3)	0.67916 (3)	0.73266 (3)	0.0441 (1)
Cl1	0.96491 (6)	0.77037 (6)	0.59685 (5)	0.0610 (2)
O1	0.8288 (2)	−0.10963 (14)	0.97544 (16)	0.0760 (8)
O2	0.67208 (19)	1.45186 (14)	0.49834 (14)	0.0688 (7)
O3	0.60727 (16)	0.60189 (14)	0.84342 (14)	0.0557 (6)
N1	0.83399 (18)	1.64559 (16)	−0.12340 (16)	0.0505 (7)
N2	0.83490 (17)	1.59740 (15)	0.04514 (15)	0.0465 (7)
N3	0.65781 (17)	1.01475 (15)	0.72708 (16)	0.0456 (6)
N4	0.69914 (18)	0.83954 (15)	0.76500 (16)	0.0519 (7)
N5	0.83206 (16)	0.50934 (15)	0.71176 (15)	0.0465 (7)
N6	0.85574 (16)	0.33001 (15)	0.74462 (15)	0.0416 (6)
N7	0.71164 (18)	−0.29343 (16)	1.59221 (16)	0.0496 (7)
N8	0.69930 (17)	−0.24606 (16)	1.42776 (16)	0.0467 (7)
C1	0.9383 (2)	1.6657 (2)	−0.1235 (2)	0.0624 (10)
C2	0.7740 (2)	1.6045 (2)	−0.0203 (2)	0.0544 (9)
C3	0.9399 (2)	1.6361 (3)	−0.0219 (2)	0.0669 (11)
C4	0.6801 (2)	1.5476 (2)	0.2179 (2)	0.0559 (9)
C5	0.7940 (2)	1.55776 (18)	0.16115 (19)	0.0465 (8)
C6	0.8683 (3)	1.5293 (3)	0.2169 (2)	0.0676 (11)
C7	0.8280 (3)	1.4919 (3)	0.3293 (2)	0.0731 (11)
C8	0.7149 (3)	1.48293 (19)	0.3842 (2)	0.0549 (9)
C9	0.6396 (3)	1.5097 (2)	0.3302 (2)	0.0589 (9)
C10	0.6700 (2)	1.34167 (18)	0.54990 (19)	0.0469 (8)
C11	0.6346 (2)	1.31692 (19)	0.66134 (19)	0.0445 (8)
C12	0.6999 (2)	1.2599 (2)	0.4957 (2)	0.0577 (9)
C13	0.6945 (2)	1.1517 (2)	0.5548 (2)	0.0571 (9)
C14	0.63090 (19)	1.20996 (18)	0.72022 (19)	0.0425 (7)
C15	0.66031 (19)	1.12626 (18)	0.66690 (19)	0.0423 (7)
C16	0.5957 (2)	0.9700 (2)	0.8342 (2)	0.0620 (9)
C17	0.6216 (3)	0.8632 (2)	0.8561 (2)	0.0636 (10)
C18	0.7187 (2)	0.93270 (19)	0.6901 (2)	0.0509 (8)
C19	0.8186 (2)	0.41719 (19)	0.78742 (19)	0.0456 (8)
C20	0.8798 (2)	0.4799 (2)	0.6154 (2)	0.0519 (8)
C21	0.8948 (2)	0.3713 (2)	0.6331 (2)	0.0536 (9)
C22	0.84856 (19)	0.21715 (18)	0.80412 (19)	0.0432 (8)
C23	0.7961 (3)	0.1899 (2)	0.9157 (2)	0.0779 (12)
C24	0.7895 (3)	0.0817 (2)	0.9744 (2)	0.0825 (12)
C25	0.8900 (2)	0.13555 (19)	0.7517 (2)	0.0462 (8)
C26	0.8822 (2)	0.0267 (2)	0.8120 (2)	0.0497 (8)
C27	0.8334 (2)	0.0012 (2)	0.9223 (2)	0.0541 (9)
C28	0.7946 (3)	−0.1378 (2)	1.0886 (2)	0.0593 (10)
C29	0.8731 (3)	−0.1478 (4)	1.1373 (3)	0.1008 (16)
C30	0.6857 (3)	−0.1647 (3)	1.1507 (3)	0.0754 (12)
C31	0.6537 (3)	−0.1984 (3)	1.2625 (3)	0.0693 (11)
C32	0.8403 (3)	−0.1825 (4)	1.2488 (3)	0.1027 (16)
C33	0.7314 (2)	−0.20775 (19)	1.3121 (2)	0.0476 (8)
C34	0.5980 (2)	−0.2919 (3)	1.5001 (3)	0.0744 (13)
C35	0.7643 (2)	−0.2506 (2)	1.4885 (2)	0.0555 (9)
C36	0.6072 (2)	−0.3191 (3)	1.5991 (2)	0.0682 (10)
O4	0.7709 (4)	0.3324 (4)	0.0926 (4)	0.168 (2)
N9	0.6951 (4)	0.1770 (4)	0.2291 (4)	0.1182 (19)
C37	0.8015 (5)	0.1377 (5)	0.2378 (5)	0.170 (4)
C38	0.5998 (6)	0.1098 (5)	0.3003 (5)	0.170 (3)
C39	0.6847 (6)	0.2690 (5)	0.1628 (5)	0.142 (3)
O5	0.0859 (3)	1.0060 (3)	0.5680 (3)	0.1261 (14)
Cl2	0.53260 (6)	0.35717 (5)	0.92795 (5)	0.0602 (2)
H1	0.99960	1.69570	−0.18530	0.0750*
H2	0.69830	1.58280	0.00450	0.0650*
H3	1.00170	1.64100	−0.00090	0.0800*
H3A	0.563 (2)	0.622 (2)	0.8997 (19)	0.0840*
H3B	0.598 (3)	0.5332 (15)	0.853 (2)	0.0840*
H4	0.62940	1.56650	0.18050	0.0670*
H6	0.94590	1.53510	0.17900	0.0810*
H7	0.87840	1.47300	0.36710	0.0880*
H9	0.56210	1.50250	0.36840	0.0710*
H11	0.61310	1.37280	0.69730	0.0530*
H12	0.72360	1.27710	0.42000	0.0690*
H13	0.71400	1.09580	0.51870	0.0690*
H14	0.60870	1.19350	0.79590	0.0510*
H16	0.54520	1.00650	0.88260	0.0740*
H17	0.59120	0.81280	0.92320	0.0760*
H18	0.76920	0.94090	0.61910	0.0610*
H19	0.78720	0.41230	0.86190	0.0550*
H20	0.89910	0.52870	0.54670	0.0620*
H21	0.92550	0.33170	0.58070	0.0640*
H23	0.76510	0.24460	0.95170	0.0940*
H24	0.75490	0.06380	1.04990	0.0990*
H25	0.92330	0.15280	0.67610	0.0550*
H26	0.91060	−0.02870	0.77650	0.0600*
H29	0.94890	−0.13140	1.09540	0.1210*
H30	0.63170	−0.16050	1.11760	0.0910*
H31	0.57800	−0.21480	1.30440	0.0830*
H32	0.89470	−0.18870	1.28170	0.1240*
H34	0.53450	−0.30220	1.48370	0.0890*
H35	0.83920	−0.22590	1.45970	0.0670*
H36	0.54970	−0.35110	1.66360	0.0820*
H37A	0.85450	0.13770	0.16660	0.2550*
H37B	0.79180	0.06440	0.28380	0.2550*
H37C	0.82970	0.18470	0.26880	0.2550*
H38A	0.53170	0.14790	0.29720	0.2550*
H38B	0.60040	0.09310	0.37350	0.2550*
H38C	0.60270	0.04280	0.27840	0.2550*
H39	0.61220	0.29140	0.16490	0.1710*
H5A	0.020 (3)	1.036 (4)	0.569 (5)	0.1890*
H5B	0.075 (4)	0.9290 (15)	0.588 (5)	0.1890*

	U11	U22	U33	U12	U13	U23
Mn1	0.0548 (2)	0.0355 (2)	0.0343 (2)	0.0009 (2)	−0.0104 (2)	−0.0032 (2)
Cl1	0.0563 (4)	0.0623 (4)	0.0507 (4)	−0.0080 (3)	−0.0080 (3)	−0.0035 (3)
O1	0.1391 (19)	0.0409 (10)	0.0501 (12)	0.0153 (11)	−0.0398 (12)	−0.0088 (8)
O2	0.1201 (17)	0.0417 (10)	0.0388 (10)	0.0261 (10)	−0.0261 (10)	−0.0092 (8)
O3	0.0631 (12)	0.0446 (10)	0.0442 (10)	−0.0052 (9)	0.0009 (8)	−0.0111 (8)
N1	0.0627 (14)	0.0466 (11)	0.0370 (11)	0.0064 (10)	−0.0129 (10)	−0.0093 (9)
N2	0.0541 (12)	0.0433 (11)	0.0392 (11)	0.0091 (9)	−0.0153 (10)	−0.0088 (9)
N3	0.0521 (12)	0.0367 (10)	0.0414 (11)	0.0039 (9)	−0.0115 (9)	−0.0061 (8)
N4	0.0667 (14)	0.0382 (11)	0.0427 (12)	0.0023 (10)	−0.0131 (10)	−0.0051 (9)
N5	0.0520 (12)	0.0410 (11)	0.0377 (11)	0.0012 (9)	−0.0075 (9)	−0.0065 (9)
N6	0.0436 (11)	0.0415 (10)	0.0360 (10)	0.0045 (8)	−0.0110 (8)	−0.0083 (8)
N7	0.0559 (13)	0.0480 (11)	0.0424 (12)	0.0009 (10)	−0.0155 (10)	−0.0093 (9)
N8	0.0494 (12)	0.0455 (11)	0.0468 (12)	0.0013 (9)	−0.0207 (10)	−0.0086 (9)
C1	0.0549 (17)	0.0725 (18)	0.0451 (16)	0.0057 (14)	−0.0078 (12)	−0.0047 (13)
C2	0.0600 (16)	0.0605 (16)	0.0391 (14)	−0.0027 (13)	−0.0164 (12)	−0.0065 (12)
C3	0.0534 (17)	0.085 (2)	0.0570 (18)	0.0036 (15)	−0.0198 (14)	−0.0089 (15)
C4	0.0616 (17)	0.0607 (16)	0.0427 (14)	0.0002 (13)	−0.0217 (13)	−0.0030 (12)
C5	0.0632 (16)	0.0364 (12)	0.0405 (13)	0.0110 (11)	−0.0204 (12)	−0.0101 (10)
C6	0.0632 (18)	0.087 (2)	0.0526 (17)	0.0195 (15)	−0.0246 (14)	−0.0165 (15)
C7	0.083 (2)	0.089 (2)	0.0544 (18)	0.0326 (18)	−0.0382 (17)	−0.0187 (16)
C8	0.088 (2)	0.0369 (13)	0.0369 (13)	0.0153 (13)	−0.0230 (14)	−0.0065 (10)
C9	0.0710 (18)	0.0526 (16)	0.0446 (15)	−0.0004 (13)	−0.0158 (13)	−0.0033 (12)
C10	0.0602 (15)	0.0402 (13)	0.0404 (13)	0.0145 (11)	−0.0220 (12)	−0.0080 (10)
C11	0.0502 (14)	0.0429 (13)	0.0418 (13)	0.0116 (10)	−0.0166 (11)	−0.0152 (10)
C12	0.089 (2)	0.0469 (14)	0.0353 (13)	0.0180 (13)	−0.0226 (13)	−0.0103 (11)
C13	0.086 (2)	0.0427 (13)	0.0432 (14)	0.0161 (13)	−0.0233 (14)	−0.0146 (11)
C14	0.0446 (13)	0.0451 (13)	0.0344 (12)	0.0049 (10)	−0.0116 (10)	−0.0081 (10)
C15	0.0454 (13)	0.0397 (12)	0.0399 (13)	0.0055 (10)	−0.0155 (10)	−0.0072 (10)
C16	0.0716 (18)	0.0495 (15)	0.0473 (15)	0.0047 (13)	−0.0013 (13)	−0.0103 (12)
C17	0.083 (2)	0.0442 (15)	0.0436 (15)	−0.0056 (13)	−0.0059 (14)	0.0021 (12)
C18	0.0585 (15)	0.0408 (13)	0.0435 (14)	0.0051 (11)	−0.0099 (11)	−0.0062 (11)
C19	0.0492 (14)	0.0438 (13)	0.0376 (13)	0.0026 (11)	−0.0074 (10)	−0.0107 (10)
C20	0.0611 (16)	0.0463 (14)	0.0350 (13)	0.0012 (12)	−0.0054 (11)	−0.0036 (11)
C21	0.0671 (17)	0.0480 (14)	0.0368 (13)	0.0043 (12)	−0.0074 (12)	−0.0116 (11)
C22	0.0477 (14)	0.0391 (12)	0.0423 (13)	0.0064 (10)	−0.0176 (11)	−0.0080 (10)
C23	0.134 (3)	0.0428 (15)	0.0407 (15)	0.0193 (17)	−0.0119 (17)	−0.0138 (12)
C24	0.148 (3)	0.0470 (16)	0.0349 (15)	0.0156 (18)	−0.0157 (17)	−0.0068 (12)
C25	0.0493 (14)	0.0463 (13)	0.0414 (13)	0.0062 (11)	−0.0132 (11)	−0.0133 (11)
C26	0.0583 (15)	0.0448 (13)	0.0491 (15)	0.0110 (11)	−0.0198 (12)	−0.0183 (11)
C27	0.0780 (18)	0.0400 (13)	0.0465 (15)	0.0105 (12)	−0.0286 (13)	−0.0076 (11)
C28	0.096 (2)	0.0367 (13)	0.0478 (16)	0.0071 (14)	−0.0328 (16)	−0.0058 (11)
C29	0.082 (2)	0.160 (4)	0.0516 (19)	−0.047 (2)	−0.0217 (18)	0.000 (2)
C30	0.082 (2)	0.089 (2)	0.066 (2)	0.0223 (19)	−0.0447 (19)	−0.0168 (17)
C31	0.0574 (17)	0.090 (2)	0.0640 (19)	0.0093 (15)	−0.0315 (15)	−0.0129 (16)
C32	0.065 (2)	0.185 (4)	0.0519 (19)	−0.045 (2)	−0.0275 (16)	0.004 (2)
C33	0.0572 (15)	0.0385 (12)	0.0489 (15)	0.0020 (11)	−0.0242 (12)	−0.0061 (11)
C34	0.0487 (16)	0.112 (3)	0.0601 (19)	−0.0149 (16)	−0.0154 (14)	−0.0175 (18)
C35	0.0522 (15)	0.0619 (16)	0.0492 (16)	−0.0068 (12)	−0.0206 (13)	−0.0024 (12)
C36	0.0571 (17)	0.093 (2)	0.0488 (17)	−0.0147 (15)	−0.0073 (13)	−0.0191 (15)
O4	0.222 (5)	0.140 (3)	0.162 (4)	−0.001 (3)	−0.062 (3)	−0.076 (3)
N9	0.127 (3)	0.115 (3)	0.144 (4)	0.022 (3)	−0.058 (3)	−0.075 (3)
C37	0.167 (6)	0.189 (6)	0.227 (7)	0.055 (5)	−0.119 (5)	−0.118 (6)
C38	0.183 (6)	0.162 (6)	0.181 (6)	−0.023 (5)	−0.039 (5)	−0.095 (5)
C39	0.174 (6)	0.112 (4)	0.152 (6)	0.013 (4)	−0.042 (5)	−0.076 (4)
O5	0.132 (3)	0.106 (2)	0.111 (2)	−0.0022 (18)	−0.011 (2)	−0.020 (2)
Cl2	0.0623 (4)	0.0513 (4)	0.0494 (4)	−0.0023 (3)	0.0038 (3)	−0.0143 (3)

Mn1—Cl1	2.5535 (9)	C16—C17	1.342 (4)
Mn1—O3	2.263 (2)	C20—C21	1.338 (4)
Mn1—N4	2.264 (2)	C22—C25	1.369 (3)
Mn1—N5	2.257 (2)	C22—C23	1.376 (3)
Mn1—N1i	2.227 (2)	C23—C24	1.380 (4)
Mn1—N7ii	2.272 (2)	C24—C27	1.360 (4)
O1—C27	1.390 (3)	C25—C26	1.392 (4)
O1—C28	1.389 (3)	C26—C27	1.357 (3)
O2—C8	1.399 (3)	C28—C30	1.349 (5)
O2—C10	1.380 (3)	C28—C29	1.352 (5)
O3—H3B	0.85 (2)	C29—C32	1.371 (5)
O3—H3A	0.86 (2)	C30—C31	1.375 (5)
O4—C39	1.317 (9)	C31—C33	1.352 (5)
O5—H5A	0.88 (5)	C32—C33	1.349 (5)
O5—H5B	0.95 (3)	C34—C36	1.337 (4)
N1—C2	1.313 (3)	C1—H1	0.9300
N1—C1	1.359 (4)	C2—H2	0.9300
N2—C3	1.356 (3)	C3—H3	0.9300
N2—C2	1.345 (3)	C4—H4	0.9300
N2—C5	1.427 (3)	C6—H6	0.9300
N3—C16	1.368 (3)	C7—H7	0.9300
N3—C18	1.338 (3)	C9—H9	0.9300
N3—C15	1.425 (3)	C11—H11	0.9300
N4—C18	1.309 (3)	C12—H12	0.9300
N4—C17	1.365 (3)	C13—H13	0.9300
N5—C20	1.366 (3)	C14—H14	0.9300
N5—C19	1.309 (3)	C16—H16	0.9300
N6—C21	1.376 (3)	C17—H17	0.9300
N6—C22	1.432 (3)	C18—H18	0.9300
N6—C19	1.352 (3)	C19—H19	0.9300
N7—C36	1.347 (4)	C20—H20	0.9300
N7—C35	1.305 (3)	C21—H21	0.9300
N8—C34	1.365 (4)	C23—H23	0.9300
N8—C35	1.339 (3)	C24—H24	0.9300
N8—C33	1.426 (3)	C25—H25	0.9300
N9—C37	1.428 (9)	C26—H26	0.9300
N9—C38	1.416 (9)	C29—H29	0.9300
N9—C39	1.297 (8)	C30—H30	0.9300
C1—C3	1.333 (4)	C31—H31	0.9300
C4—C9	1.381 (3)	C32—H32	0.9300
C4—C5	1.368 (4)	C34—H34	0.9300
C5—C6	1.371 (4)	C35—H35	0.9300
C6—C7	1.382 (3)	C36—H36	0.9300
C7—C8	1.355 (5)	C37—H37C	0.9600
C8—C9	1.364 (5)	C37—H37A	0.9600
C10—C12	1.374 (3)	C37—H37B	0.9600
C10—C11	1.368 (3)	C38—H38A	0.9600
C11—C14	1.370 (3)	C38—H38B	0.9600
C12—C13	1.383 (4)	C38—H38C	0.9600
C13—C15	1.376 (3)	C39—H39	0.9300
C14—C15	1.387 (3)
Cl1—Mn1—O3	175.97 (5)	O1—C27—C26	116.2 (2)
Cl1—Mn1—N4	93.74 (6)	O1—C28—C30	121.0 (3)
Cl1—Mn1—N5	93.94 (6)	O1—C28—C29	119.5 (3)
Cl1—Mn1—N1i	94.66 (6)	C29—C28—C30	119.2 (3)
Cl1—Mn1—N7ii	88.74 (6)	C28—C29—C32	119.6 (4)
O3—Mn1—N4	85.63 (7)	C28—C30—C31	120.7 (4)
O3—Mn1—N5	86.57 (7)	C30—C31—C33	120.6 (4)
O3—Mn1—N1i	89.34 (8)	C29—C32—C33	121.9 (4)
O3—Mn1—N7ii	87.27 (7)	N8—C33—C31	120.8 (3)
N4—Mn1—N5	172.07 (8)	N8—C33—C32	121.1 (3)
N1i—Mn1—N4	91.75 (8)	C31—C33—C32	118.1 (3)
N4—Mn1—N7ii	88.75 (8)	N8—C34—C36	107.1 (3)
N1i—Mn1—N5	89.60 (7)	N7—C35—N8	113.0 (2)
N5—Mn1—N7ii	89.44 (7)	N7—C36—C34	110.3 (2)
N1i—Mn1—N7ii	176.52 (8)	C3—C1—H1	125.00
C27—O1—C28	117.9 (2)	N1—C1—H1	125.00
C8—O2—C10	118.23 (19)	N1—C2—H2	124.00
H3A—O3—H3B	109 (2)	N2—C2—H2	124.00
Mn1—O3—H3B	118 (2)	N2—C3—H3	126.00
Mn1—O3—H3A	125.6 (18)	C1—C3—H3	126.00
H5A—O5—H5B	107 (5)	C5—C4—H4	120.00
Mn1ii—N1—C2	128.12 (19)	C9—C4—H4	120.00
C1—N1—C2	104.9 (2)	C5—C6—H6	120.00
Mn1ii—N1—C1	127.02 (16)	C7—C6—H6	120.00
C2—N2—C3	105.7 (2)	C6—C7—H7	120.00
C3—N2—C5	128.5 (2)	C8—C7—H7	120.00
C2—N2—C5	125.8 (2)	C4—C9—H9	120.00
C16—N3—C18	105.9 (2)	C8—C9—H9	121.00
C15—N3—C16	127.6 (2)	C14—C11—H11	120.00
C15—N3—C18	126.5 (2)	C10—C11—H11	120.00
Mn1—N4—C17	131.48 (16)	C10—C12—H12	120.00
Mn1—N4—C18	123.34 (17)	C13—C12—H12	120.00
C17—N4—C18	105.1 (2)	C12—C13—H13	120.00
C19—N5—C20	104.9 (2)	C15—C13—H13	120.00
Mn1—N5—C20	126.71 (16)	C11—C14—H14	120.00
Mn1—N5—C19	128.22 (16)	C15—C14—H14	120.00
C19—N6—C21	106.1 (2)	C17—C16—H16	127.00
C21—N6—C22	127.4 (2)	N3—C16—H16	127.00
C19—N6—C22	126.41 (19)	N4—C17—H17	125.00
C35—N7—C36	104.8 (2)	C16—C17—H17	125.00
Mn1i—N7—C36	126.59 (16)	N4—C18—H18	124.00
Mn1i—N7—C35	128.65 (19)	N3—C18—H18	124.00
C33—N8—C34	127.7 (2)	N5—C19—H19	124.00
C33—N8—C35	127.4 (2)	N6—C19—H19	124.00
C34—N8—C35	104.9 (2)	C21—C20—H20	125.00
C38—N9—C39	121.6 (6)	N5—C20—H20	125.00
C37—N9—C39	123.0 (6)	N6—C21—H21	127.00
C37—N9—C38	115.4 (5)	C20—C21—H21	127.00
N1—C1—C3	110.0 (2)	C22—C23—H23	120.00
N1—C2—N2	112.0 (2)	C24—C23—H23	120.00
N2—C3—C1	107.4 (2)	C23—C24—H24	120.00
C5—C4—C9	120.8 (3)	C27—C24—H24	120.00
N2—C5—C6	120.5 (2)	C26—C25—H25	120.00
N2—C5—C4	120.3 (2)	C22—C25—H25	120.00
C4—C5—C6	119.3 (2)	C25—C26—H26	120.00
C5—C6—C7	120.1 (3)	C27—C26—H26	120.00
C6—C7—C8	119.8 (3)	C32—C29—H29	120.00
O2—C8—C7	120.8 (3)	C28—C29—H29	120.00
O2—C8—C9	118.1 (3)	C31—C30—H30	120.00
C7—C8—C9	121.0 (2)	C28—C30—H30	120.00
C4—C9—C8	119.1 (3)	C33—C31—H31	120.00
O2—C10—C11	115.6 (2)	C30—C31—H31	120.00
O2—C10—C12	123.8 (2)	C29—C32—H32	119.00
C11—C10—C12	120.6 (2)	C33—C32—H32	119.00
C10—C11—C14	120.2 (2)	N8—C34—H34	127.00
C10—C12—C13	119.4 (2)	C36—C34—H34	126.00
C12—C13—C15	120.3 (2)	N8—C35—H35	123.00
C11—C14—C15	120.0 (2)	N7—C35—H35	124.00
C13—C15—C14	119.5 (2)	N7—C36—H36	125.00
N3—C15—C13	119.9 (2)	C34—C36—H36	125.00
N3—C15—C14	120.5 (2)	O4—C39—N9	123.8 (7)
N3—C16—C17	106.8 (2)	N9—C37—H37B	109.00
N4—C17—C16	109.8 (2)	N9—C37—H37C	109.00
N3—C18—N4	112.4 (2)	H37A—C37—H37B	110.00
N5—C19—N6	112.1 (2)	H37A—C37—H37C	109.00
N5—C20—C21	110.9 (2)	H37B—C37—H37C	109.00
N6—C21—C20	106.1 (2)	N9—C37—H37A	109.00
N6—C22—C23	119.4 (2)	N9—C38—H38A	109.00
N6—C22—C25	121.2 (2)	N9—C38—H38C	109.00
C23—C22—C25	119.4 (2)	H38A—C38—H38B	110.00
C22—C23—C24	120.2 (2)	H38A—C38—H38C	109.00
C23—C24—C27	120.3 (2)	H38B—C38—H38C	109.00
C22—C25—C26	119.8 (2)	N9—C38—H38B	109.00
C25—C26—C27	120.3 (2)	O4—C39—H39	118.00
C24—C27—C26	120.1 (2)	N9—C39—H39	118.00
O1—C27—C24	123.7 (2)
Cl1—Mn1—N4—C17	−148.6 (3)	C19—N5—C20—C21	0.0 (3)
Cl1—Mn1—N4—C18	35.1 (2)	C21—N6—C19—N5	−0.4 (3)
O3—Mn1—N4—C17	35.4 (3)	C22—N6—C19—N5	−176.8 (2)
O3—Mn1—N4—C18	−140.9 (2)	C19—N6—C21—C20	0.4 (3)
N1i—Mn1—N4—C17	−53.9 (3)	C22—N6—C21—C20	176.7 (2)
N1i—Mn1—N4—C18	129.9 (2)	C19—N6—C22—C23	2.4 (4)
N7ii—Mn1—N4—C17	122.7 (3)	C19—N6—C22—C25	−179.6 (3)
N7ii—Mn1—N4—C18	−53.5 (2)	C21—N6—C22—C23	−173.2 (3)
Cl1—Mn1—N5—C19	135.7 (2)	C21—N6—C22—C25	4.9 (4)
Cl1—Mn1—N5—C20	−49.0 (2)	C36—N7—C35—N8	0.6 (3)
O3—Mn1—N5—C19	−48.3 (2)	Mn1i—N7—C35—N8	−179.58 (16)
O3—Mn1—N5—C20	127.0 (2)	C35—N7—C36—C34	0.1 (4)
N1i—Mn1—N5—C19	41.1 (2)	Mn1i—N7—C36—C34	−179.7 (2)
N1i—Mn1—N5—C20	−143.6 (2)	C34—N8—C33—C31	10.3 (4)
N7ii—Mn1—N5—C19	−135.6 (2)	C34—N8—C33—C32	−168.0 (4)
N7ii—Mn1—N5—C20	39.7 (2)	C35—N8—C33—C31	−173.8 (3)
Cl1—Mn1—N1i—C1i	−3.7 (2)	C35—N8—C33—C32	7.9 (4)
Cl1—Mn1—N1i—C2i	174.9 (2)	C33—N8—C34—C36	177.7 (3)
O3—Mn1—N1i—C1i	176.9 (2)	C35—N8—C34—C36	1.1 (4)
O3—Mn1—N1i—C2i	−4.6 (2)	C33—N8—C35—N7	−177.7 (2)
N4—Mn1—N1i—C1i	−97.6 (2)	C34—N8—C35—N7	−1.1 (3)
N4—Mn1—N1i—C2i	81.0 (2)	C38—N9—C39—O4	−177.6 (6)
N5—Mn1—N1i—C1i	90.3 (2)	C37—N9—C39—O4	4.0 (10)
N5—Mn1—N1i—C2i	−91.2 (2)	N1—C1—C3—N2	−0.7 (4)
Cl1—Mn1—N7ii—C35ii	2.4 (2)	C9—C4—C5—C6	0.3 (4)
Cl1—Mn1—N7ii—C36ii	−177.9 (3)	C9—C4—C5—N2	−179.8 (2)
O3—Mn1—N7ii—C35ii	−178.2 (2)	C5—C4—C9—C8	0.4 (4)
O3—Mn1—N7ii—C36ii	1.6 (3)	C4—C5—C6—C7	−0.7 (5)
N4—Mn1—N7ii—C35ii	96.2 (2)	N2—C5—C6—C7	179.4 (3)
N4—Mn1—N7ii—C36ii	−84.1 (3)	C5—C6—C7—C8	0.3 (5)
N5—Mn1—N7ii—C35ii	−91.6 (2)	C6—C7—C8—C9	0.4 (5)
N5—Mn1—N7ii—C36ii	88.2 (3)	C6—C7—C8—O2	−176.0 (3)
C28—O1—C27—C24	−11.0 (5)	O2—C8—C9—C4	175.7 (2)
C28—O1—C27—C26	170.9 (3)	C7—C8—C9—C4	−0.7 (4)
C27—O1—C28—C29	−91.0 (4)	C12—C10—C11—C14	1.4 (4)
C27—O1—C28—C30	94.8 (4)	O2—C10—C11—C14	−179.1 (2)
C10—O2—C8—C7	−80.4 (4)	C11—C10—C12—C13	−0.3 (4)
C10—O2—C8—C9	103.1 (3)	O2—C10—C12—C13	−179.7 (3)
C8—O2—C10—C11	175.7 (3)	C10—C11—C14—C15	−1.7 (4)
C8—O2—C10—C12	−4.9 (4)	C10—C12—C13—C15	−0.5 (4)
C2—N1—C1—C3	0.4 (3)	C12—C13—C15—C14	0.2 (4)
Mn1ii—N1—C1—C3	179.2 (2)	C12—C13—C15—N3	−178.4 (2)
C1—N1—C2—N2	0.0 (3)	C11—C14—C15—N3	179.4 (2)
Mn1ii—N1—C2—N2	−178.81 (16)	C11—C14—C15—C13	0.9 (4)
C3—N2—C2—N1	−0.4 (3)	N3—C16—C17—N4	0.2 (4)
C5—N2—C2—N1	179.1 (2)	N5—C20—C21—N6	−0.3 (3)
C2—N2—C3—C1	0.6 (3)	C25—C22—C23—C24	2.6 (5)
C5—N2—C3—C1	−178.8 (2)	N6—C22—C25—C26	179.7 (2)
C2—N2—C5—C4	−15.7 (4)	N6—C22—C23—C24	−179.3 (3)
C2—N2—C5—C6	164.2 (3)	C23—C22—C25—C26	−2.3 (4)
C3—N2—C5—C4	163.6 (3)	C22—C23—C24—C27	−0.9 (6)
C3—N2—C5—C6	−16.5 (4)	C23—C24—C27—O1	−179.1 (3)
C16—N3—C15—C13	−157.7 (3)	C23—C24—C27—C26	−1.2 (5)
C16—N3—C15—C14	23.7 (4)	C22—C25—C26—C27	0.2 (4)
C18—N3—C15—C13	24.1 (4)	C25—C26—C27—C24	1.5 (4)
C18—N3—C15—C14	−154.5 (3)	C25—C26—C27—O1	179.6 (3)
C15—N3—C16—C17	−179.0 (3)	O1—C28—C29—C32	−175.8 (4)
C18—N3—C16—C17	−0.5 (3)	C29—C28—C30—C31	2.2 (6)
C15—N3—C18—N4	179.2 (2)	C30—C28—C29—C32	−1.5 (6)
C16—N3—C18—N4	0.6 (3)	O1—C28—C30—C31	176.4 (3)
Mn1—N4—C17—C16	−176.5 (2)	C28—C29—C32—C33	0.3 (7)
C18—N4—C17—C16	0.2 (4)	C28—C30—C31—C33	−1.6 (6)
Mn1—N4—C18—N3	176.56 (17)	C30—C31—C33—C32	0.4 (5)
C17—N4—C18—N3	−0.5 (3)	C30—C31—C33—N8	−178.0 (3)
Mn1—N5—C19—N6	176.38 (16)	C29—C32—C33—N8	178.6 (4)
C20—N5—C19—N6	0.3 (3)	C29—C32—C33—C31	0.3 (6)
Mn1—N5—C20—C21	−176.18 (18)	N8—C34—C36—N7	−0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···Cl2iii	0.86 (2)	2.29 (2)	3.1306 (19)	166 (2)
O3—H3B···Cl2	0.85 (2)	2.27 (2)	3.093 (2)	162 (3)
O5—H5A···Cl1iv	0.89 (2)	2.81 (5)	3.282 (3)	114 (4)
O5—H5B···Cl1v	0.95 (3)	2.48 (4)	3.316 (4)	148 (5)
C17—H17···Cl2iii	0.93	2.67	3.553 (3)	159
C18—H18···O5iv	0.93	2.50	3.418 (5)	170
C23—H23···O4vi	0.93	2.47	3.270 (6)	145
C35—H35···Cl1i	0.93	2.82	3.398 (3)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯Cl2i	0.86 (2)	2.29 (2)	3.1306 (19)	166 (2)
O3—H3B⋯Cl2	0.85 (2)	2.27 (2)	3.093 (2)	162 (3)
O5—H5A⋯Cl1ii	0.89 (2)	2.81 (5)	3.282 (3)	114 (4)
O5—H5B⋯Cl1iii	0.95 (3)	2.48 (4)	3.316 (4)	148 (5)
C17—H17⋯Cl2i	0.93	2.67	3.553 (3)	159
C18—H18⋯O5ii	0.93	2.50	3.418 (5)	170
C23—H23⋯O4iv	0.93	2.47	3.270 (6)	145
C35—H35⋯Cl1v	0.93	2.82	3.398 (3)	121

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .