Bis(μ-2-phenyl-quinoline-4-carboxyl-ato)bis-[aqua-(1,10-phenanthroline)(2-phenyl-quinoline-4-carboxyl-ato)manganese(II)] dihydrate.

In the centrosymmetric dinuclear title complex, [Mn(2)(C(16)H(10)NO(2))(4)(C(12)H(8)N(2))(2)(H(2)O)(2)]·2H(2)O, the Mn(II) cation is in a distorted octa-hedral coordination geometry defined by two N atoms from a 1,10-phenanthroline ligand, one water O atom and three O atoms from three 2-phenyl-quinoline-4-carboxyl-ate anions. A pair of 2-phenyl-quinoline-4-carboxyl-ate anions bridge two Mn cations, forming the dinuclear mol-ecule. An intra-moleculr O-H⋯O hydrogen bond occurs. Inter-molecular O-H⋯O and O-H⋯N hydrogen bonds are present in the crystal structure.

Related literature

For applications of coordination polymers, see: Wang et al. (2009 ▶); Xi et al. (2009 ▶); Xu et al. (2008 ▶); Ferey (2008 ▶). For a related structure, see: Shen et al. (2007 ▶).

Experimental

Crystal data

[Mn2(C16H10NO2)4(C12H8N2)2(H2O)2]·2H2O

M = 1535.35

Monoclinic,

a = 14.926 (4) Å

b = 13.847 (4) Å

c = 17.717 (5) Å

β = 96.919 (4)°

V = 3635.1 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.42 mm−1

T = 296 K

0.35 × 0.15 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.927, T max = 0.951

31242 measured reflections

8315 independent reflections

5656 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.113

S = 1.03

8315 reflections

512 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811039341/xu5330sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039341/xu5330Isup2.hkl

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

[Mn2(C16H10NO2)4(C12H8N2)2(H2O)2]·2H2O	F(000) = 1588
Mr = 1535.35	Dx = 1.403 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6315 reflections
a = 14.926 (4) Å	θ = 2.2–25.3°
b = 13.847 (4) Å	µ = 0.42 mm−1
c = 17.717 (5) Å	T = 296 K
β = 96.919 (4)°	Block, light-yellow
V = 3635.1 (18) Å3	0.35 × 0.15 × 0.12 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	8315 independent reflections
Radiation source: fine-focus sealed tube	5656 reflections with I > 2σ(I)
graphite	Rint = 0.044
φ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −17→19
Tmin = 0.927, Tmax = 0.951	k = −17→17
31242 measured reflections	l = −22→22

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0558P)2 + 0.2051P] where P = (Fo2 + 2Fc2)/3
8315 reflections	(Δ/σ)max = 0.001
512 parameters	Δρmax = 0.41 e Å−3
4 restraints	Δρmin = −0.28 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
Mn1	0.077680 (18)	0.13501 (2)	0.951424 (14)	0.03543 (10)
O1	0.22272 (9)	0.12800 (10)	0.98381 (8)	0.0504 (4)
O2	0.24413 (10)	0.27644 (12)	1.03173 (10)	0.0738 (5)
O3	0.06564 (9)	−0.01826 (10)	0.93138 (7)	0.0443 (3)
O4	−0.04776 (10)	−0.12260 (10)	0.93530 (7)	0.0529 (4)
O5	0.07358 (10)	0.29333 (10)	0.97558 (8)	0.0445 (3)
O6	0.26767 (16)	0.5645 (2)	0.39858 (18)	0.1290 (10)
N1	0.53501 (11)	0.09953 (14)	1.12225 (10)	0.0557 (5)
N2	−0.03456 (11)	−0.08570 (11)	0.65569 (8)	0.0402 (4)
N3	−0.06204 (10)	0.15689 (12)	0.88748 (9)	0.0425 (4)
N4	0.09674 (10)	0.16239 (11)	0.82681 (8)	0.0373 (4)
C1	0.27011 (13)	0.19290 (16)	1.01920 (11)	0.0463 (5)
C2	0.36515 (12)	0.16419 (15)	1.05267 (10)	0.0428 (5)
C3	0.38370 (13)	0.06909 (15)	1.06611 (10)	0.0447 (5)
H3	0.3395	0.0234	1.0511	0.054*
C4	0.43546 (13)	0.23362 (16)	1.07405 (11)	0.0488 (5)
C5	0.42841 (15)	0.33411 (18)	1.06345 (15)	0.0666 (7)
H5	0.3738	0.3605	1.0423	0.080*
C6	0.50050 (18)	0.3939 (2)	1.08366 (18)	0.0839 (9)
H6	0.4943	0.4602	1.0766	0.101*
C7	0.58388 (18)	0.3551 (2)	1.11501 (19)	0.0895 (10)
H7	0.6329	0.3958	1.1277	0.107*
C8	0.59324 (16)	0.2594 (2)	1.12680 (16)	0.0788 (8)
H8	0.6487	0.2349	1.1478	0.095*
C9	0.51972 (13)	0.19506 (17)	1.10771 (12)	0.0555 (6)
C10	0.46890 (13)	0.03769 (16)	1.10258 (11)	0.0479 (5)
C11	0.48590 (14)	−0.06496 (17)	1.12264 (13)	0.0535 (5)
C12	0.53980 (19)	−0.0895 (2)	1.18959 (17)	0.0868 (9)
H12	0.5677	−0.0413	1.2206	0.104*
C13	0.5518 (2)	−0.1856 (3)	1.2101 (2)	0.1048 (11)
H13	0.5868	−0.2012	1.2554	0.126*
C14	0.44751 (15)	−0.13894 (17)	1.07692 (15)	0.0610 (6)
H14	0.4117	−0.1242	1.0318	0.073*
C15	0.46197 (18)	−0.2346 (2)	1.09785 (18)	0.0808 (8)
H15	0.4367	−0.2835	1.0662	0.097*
C16	0.5133 (2)	−0.2577 (2)	1.1650 (2)	0.1006 (11)
H16	0.5217	−0.3219	1.1795	0.121*
C17	0.00152 (13)	−0.06932 (13)	0.90100 (10)	0.0393 (4)
C18	−0.01582 (13)	−0.07117 (12)	0.81476 (9)	0.0361 (4)
C19	0.05738 (13)	−0.06910 (12)	0.77495 (10)	0.0369 (4)
H19	0.1150	−0.0627	0.8010	0.044*
C20	−0.10419 (13)	−0.07755 (13)	0.77399 (10)	0.0378 (4)
C21	−0.18619 (14)	−0.07534 (15)	0.80722 (12)	0.0502 (5)
H21	−0.1846	−0.0707	0.8597	0.060*
C22	−0.26733 (15)	−0.07998 (17)	0.76262 (13)	0.0592 (6)
H22	−0.3204	−0.0778	0.7851	0.071*
C23	−0.27174 (15)	−0.08801 (17)	0.68346 (13)	0.0588 (6)
H23	−0.3275	−0.0922	0.6540	0.071*
C24	−0.19513 (14)	−0.08966 (15)	0.64978 (12)	0.0511 (5)
H24	−0.1989	−0.0945	0.5971	0.061*
C25	−0.10912 (13)	−0.08409 (13)	0.69350 (10)	0.0388 (4)
C26	0.04644 (13)	−0.07653 (12)	0.69469 (10)	0.0364 (4)
C27	0.12600 (14)	−0.07413 (13)	0.65102 (11)	0.0427 (5)
C28	0.11378 (16)	−0.06426 (16)	0.57216 (12)	0.0607 (6)
H28	0.0557	−0.0602	0.5466	0.073*
C29	0.1872 (2)	−0.0604 (2)	0.53144 (15)	0.0793 (8)
H29	0.1778	−0.0548	0.4788	0.095*
C30	0.21377 (15)	−0.07807 (16)	0.68732 (13)	0.0579 (6)
H30	0.2236	−0.0844	0.7399	0.069*
C31	0.28697 (18)	−0.0727 (2)	0.64598 (16)	0.0776 (8)
H31	0.3454	−0.0746	0.6711	0.093*
C32	0.2735 (2)	−0.0646 (2)	0.56783 (17)	0.0811 (8)
H32	0.3225	−0.0620	0.5401	0.097*
C33	−0.13864 (14)	0.15679 (16)	0.91749 (14)	0.0568 (6)
H33	−0.1366	0.1491	0.9698	0.068*
C34	−0.22241 (15)	0.16763 (18)	0.87456 (17)	0.0708 (7)
H34	−0.2750	0.1682	0.8979	0.085*
C35	−0.22613 (15)	0.17737 (18)	0.79814 (17)	0.0706 (7)
H35	−0.2818	0.1837	0.7688	0.085*
C36	−0.14736 (14)	0.17799 (15)	0.76307 (13)	0.0533 (6)
C37	−0.06530 (12)	0.16867 (13)	0.81122 (11)	0.0394 (4)
C38	−0.14444 (18)	0.18754 (17)	0.68263 (14)	0.0675 (7)
H38	−0.1983	0.1933	0.6505	0.081*
C39	−0.0665 (2)	0.18842 (16)	0.65274 (12)	0.0643 (7)
H39	−0.0672	0.1953	0.6004	0.077*
C40	0.01816 (15)	0.17908 (14)	0.69947 (10)	0.0460 (5)
C41	0.01878 (13)	0.17047 (12)	0.77883 (10)	0.0364 (4)
C42	0.10130 (18)	0.18032 (16)	0.67071 (12)	0.0590 (6)
H42	0.1036	0.1870	0.6187	0.071*
C43	0.17865 (17)	0.17165 (16)	0.71898 (12)	0.0579 (6)
H43	0.2343	0.1713	0.7004	0.070*
C44	0.17374 (14)	0.16325 (15)	0.79703 (11)	0.0462 (5)
H44	0.2273	0.1580	0.8296	0.055*
H5A	0.1296 (12)	0.3012 (19)	0.9910 (15)	0.092 (10)*
H6A	0.246 (4)	0.511 (3)	0.418 (3)	0.27 (3)*
H5B	0.0596 (16)	0.3279 (16)	0.9376 (11)	0.074 (8)*
H6B	0.3245 (14)	0.556 (3)	0.393 (2)	0.147 (16)*

	U11	U22	U33	U12	U13	U23
Mn1	0.03206 (16)	0.04590 (18)	0.02736 (14)	−0.00132 (13)	−0.00034 (10)	0.00228 (12)
O1	0.0319 (7)	0.0636 (10)	0.0529 (8)	0.0000 (7)	−0.0070 (6)	−0.0057 (7)
O2	0.0458 (9)	0.0658 (11)	0.1038 (13)	0.0064 (8)	−0.0157 (9)	−0.0141 (10)
O3	0.0499 (8)	0.0459 (8)	0.0357 (7)	−0.0008 (6)	−0.0006 (6)	−0.0022 (6)
O4	0.0740 (10)	0.0543 (9)	0.0314 (7)	−0.0159 (7)	0.0106 (7)	0.0016 (6)
O5	0.0489 (9)	0.0483 (9)	0.0351 (7)	0.0036 (7)	0.0004 (6)	0.0055 (6)
O6	0.0584 (15)	0.160 (3)	0.165 (3)	−0.0228 (16)	−0.0017 (15)	0.058 (2)
N1	0.0352 (10)	0.0640 (12)	0.0643 (11)	0.0023 (9)	−0.0086 (8)	−0.0085 (10)
N2	0.0482 (10)	0.0409 (9)	0.0310 (8)	−0.0013 (7)	0.0028 (7)	−0.0004 (7)
N3	0.0327 (9)	0.0501 (10)	0.0436 (9)	0.0020 (7)	−0.0003 (7)	0.0045 (7)
N4	0.0392 (9)	0.0388 (9)	0.0333 (8)	−0.0007 (7)	0.0021 (7)	0.0023 (6)
C1	0.0342 (11)	0.0598 (14)	0.0438 (11)	0.0004 (10)	−0.0007 (9)	−0.0015 (10)
C2	0.0312 (10)	0.0594 (13)	0.0370 (10)	−0.0011 (9)	0.0013 (8)	−0.0040 (9)
C3	0.0324 (10)	0.0601 (14)	0.0411 (10)	−0.0051 (9)	0.0020 (8)	−0.0039 (9)
C4	0.0360 (11)	0.0587 (14)	0.0507 (11)	−0.0005 (10)	0.0005 (9)	−0.0075 (10)
C5	0.0440 (13)	0.0629 (16)	0.0895 (18)	−0.0001 (11)	−0.0059 (12)	−0.0023 (13)
C6	0.0644 (18)	0.0606 (16)	0.123 (2)	−0.0089 (14)	−0.0045 (16)	−0.0095 (16)
C7	0.0492 (16)	0.076 (2)	0.136 (3)	−0.0146 (14)	−0.0169 (16)	−0.0197 (18)
C8	0.0416 (13)	0.0723 (18)	0.115 (2)	−0.0048 (12)	−0.0214 (13)	−0.0172 (16)
C9	0.0342 (11)	0.0675 (16)	0.0622 (13)	−0.0025 (10)	−0.0045 (10)	−0.0117 (11)
C10	0.0325 (11)	0.0664 (15)	0.0438 (11)	0.0006 (10)	0.0002 (8)	−0.0043 (10)
C11	0.0356 (11)	0.0649 (15)	0.0607 (13)	0.0041 (10)	0.0086 (10)	0.0064 (11)
C12	0.0719 (19)	0.091 (2)	0.089 (2)	0.0023 (16)	−0.0221 (15)	0.0191 (17)
C13	0.081 (2)	0.107 (3)	0.120 (3)	0.008 (2)	−0.0144 (19)	0.048 (2)
C14	0.0473 (13)	0.0657 (16)	0.0718 (15)	0.0024 (11)	0.0153 (11)	−0.0016 (13)
C15	0.0659 (17)	0.0637 (18)	0.115 (2)	−0.0006 (14)	0.0207 (16)	0.0011 (16)
C16	0.070 (2)	0.074 (2)	0.158 (3)	0.0129 (17)	0.017 (2)	0.034 (2)
C17	0.0510 (12)	0.0358 (10)	0.0318 (9)	0.0030 (9)	0.0074 (8)	−0.0016 (8)
C18	0.0508 (12)	0.0271 (9)	0.0304 (9)	−0.0017 (8)	0.0050 (8)	−0.0009 (7)
C19	0.0452 (11)	0.0322 (10)	0.0329 (9)	−0.0028 (8)	0.0027 (8)	−0.0007 (7)
C20	0.0457 (11)	0.0300 (10)	0.0383 (10)	0.0012 (8)	0.0079 (8)	0.0007 (8)
C21	0.0544 (13)	0.0543 (13)	0.0432 (11)	0.0020 (10)	0.0108 (10)	−0.0009 (9)
C22	0.0465 (13)	0.0728 (16)	0.0600 (14)	0.0053 (11)	0.0131 (11)	−0.0003 (12)
C23	0.0471 (13)	0.0681 (15)	0.0593 (14)	0.0024 (11)	−0.0012 (11)	0.0014 (12)
C24	0.0522 (13)	0.0577 (13)	0.0416 (11)	0.0026 (11)	−0.0016 (9)	−0.0006 (10)
C25	0.0476 (11)	0.0320 (10)	0.0362 (9)	0.0016 (8)	0.0030 (8)	0.0008 (8)
C26	0.0477 (11)	0.0290 (10)	0.0330 (9)	−0.0036 (8)	0.0065 (8)	−0.0011 (7)
C27	0.0530 (12)	0.0370 (11)	0.0397 (10)	−0.0076 (9)	0.0126 (9)	−0.0050 (8)
C28	0.0676 (16)	0.0712 (16)	0.0458 (12)	−0.0172 (12)	0.0170 (11)	0.0027 (11)
C29	0.096 (2)	0.093 (2)	0.0540 (14)	−0.0284 (17)	0.0323 (15)	−0.0033 (13)
C30	0.0540 (14)	0.0623 (15)	0.0593 (14)	−0.0010 (11)	0.0145 (11)	−0.0077 (11)
C31	0.0559 (16)	0.094 (2)	0.085 (2)	−0.0095 (14)	0.0192 (14)	−0.0171 (16)
C32	0.077 (2)	0.088 (2)	0.087 (2)	−0.0254 (16)	0.0448 (16)	−0.0155 (16)
C33	0.0403 (12)	0.0635 (15)	0.0676 (14)	0.0058 (10)	0.0102 (11)	0.0108 (11)
C34	0.0357 (13)	0.0710 (17)	0.105 (2)	0.0055 (11)	0.0063 (13)	0.0196 (15)
C35	0.0376 (13)	0.0639 (16)	0.103 (2)	0.0013 (11)	−0.0219 (13)	0.0163 (15)
C36	0.0480 (13)	0.0389 (11)	0.0662 (14)	−0.0002 (10)	−0.0210 (11)	0.0051 (10)
C37	0.0385 (11)	0.0320 (10)	0.0442 (10)	0.0014 (8)	−0.0092 (8)	0.0026 (8)
C38	0.0729 (18)	0.0573 (15)	0.0612 (15)	−0.0026 (13)	−0.0377 (13)	0.0075 (12)
C39	0.097 (2)	0.0507 (14)	0.0376 (11)	0.0020 (14)	−0.0225 (12)	0.0039 (10)
C40	0.0725 (15)	0.0303 (10)	0.0329 (10)	0.0008 (10)	−0.0026 (10)	0.0021 (8)
C41	0.0479 (11)	0.0273 (9)	0.0314 (9)	0.0001 (8)	−0.0054 (8)	0.0011 (7)
C42	0.098 (2)	0.0468 (13)	0.0333 (11)	0.0043 (13)	0.0142 (12)	0.0040 (9)
C43	0.0742 (17)	0.0529 (13)	0.0527 (13)	0.0043 (12)	0.0322 (12)	0.0046 (10)
C44	0.0454 (12)	0.0493 (12)	0.0451 (11)	0.0018 (9)	0.0100 (9)	0.0049 (9)

Mn1—O1	2.1740 (14)	C16—H16	0.9300
Mn1—O3	2.1557 (15)	C17—C18	1.519 (2)
Mn1—O4i	2.1148 (14)	C18—C19	1.370 (3)
Mn1—O5	2.2358 (16)	C18—C20	1.428 (3)
Mn1—N3	2.2706 (16)	C19—C26	1.415 (2)
Mn1—N4	2.2914 (15)	C19—H19	0.9300
O1—C1	1.263 (2)	C20—C21	1.421 (3)
O2—C1	1.248 (2)	C20—C25	1.422 (3)
O3—C17	1.258 (2)	C21—C22	1.366 (3)
O4—C17	1.250 (2)	C21—H21	0.9300
O4—Mn1i	2.1148 (14)	C22—C23	1.400 (3)
O5—H5A	0.854 (17)	C22—H22	0.9300
O5—H5B	0.832 (16)	C23—C24	1.352 (3)
O6—H6A	0.89 (5)	C23—H23	0.9300
O6—H6B	0.874 (18)	C24—C25	1.419 (3)
N1—C10	1.321 (3)	C24—H24	0.9300
N1—C9	1.362 (3)	C26—C27	1.494 (3)
N2—C26	1.324 (2)	C27—C30	1.389 (3)
N2—C25	1.367 (2)	C27—C28	1.394 (3)
N3—C33	1.318 (3)	C28—C29	1.383 (3)
N3—C37	1.356 (2)	C28—H28	0.9300
N4—C44	1.321 (2)	C29—C32	1.371 (4)
N4—C41	1.360 (2)	C29—H29	0.9300
C1—C2	1.523 (3)	C30—C31	1.389 (3)
C2—C3	1.361 (3)	C30—H30	0.9300
C2—C4	1.440 (3)	C31—C32	1.379 (4)
C3—C10	1.423 (3)	C31—H31	0.9300
C3—H3	0.9300	C32—H32	0.9300
C4—C5	1.406 (3)	C33—C34	1.391 (3)
C4—C9	1.429 (3)	C33—H33	0.9300
C5—C6	1.370 (3)	C34—C35	1.355 (4)
C5—H5	0.9300	C34—H34	0.9300
C6—C7	1.407 (4)	C35—C36	1.394 (3)
C6—H6	0.9300	C35—H35	0.9300
C7—C8	1.346 (4)	C36—C37	1.412 (2)
C7—H7	0.9300	C36—C38	1.437 (3)
C8—C9	1.422 (3)	C37—C41	1.442 (3)
C8—H8	0.9300	C38—C39	1.336 (3)
C10—C11	1.479 (3)	C38—H38	0.9300
C11—C14	1.386 (3)	C39—C40	1.430 (3)
C11—C12	1.393 (3)	C39—H39	0.9300
C12—C13	1.385 (4)	C40—C42	1.397 (3)
C12—H12	0.9300	C40—C41	1.410 (2)
C13—C16	1.362 (4)	C42—C43	1.357 (3)
C13—H13	0.9300	C42—H42	0.9300
C14—C15	1.385 (3)	C43—C44	1.398 (3)
C14—H14	0.9300	C43—H43	0.9300
C15—C16	1.372 (4)	C44—H44	0.9300
C15—H15	0.9300
O4i—Mn1—O3	93.06 (5)	C19—C18—C20	119.09 (16)
O4i—Mn1—O1	93.63 (6)	C19—C18—C17	117.88 (16)
O3—Mn1—O1	93.45 (5)	C20—C18—C17	123.01 (16)
O4i—Mn1—O5	83.35 (5)	C18—C19—C26	120.86 (17)
O3—Mn1—O5	173.29 (5)	C18—C19—H19	119.6
O1—Mn1—O5	92.44 (5)	C26—C19—H19	119.6
O4i—Mn1—N3	101.43 (6)	C21—C20—C25	118.27 (17)
O3—Mn1—N3	89.76 (5)	C21—C20—C18	125.33 (17)
O1—Mn1—N3	164.42 (6)	C25—C20—C18	116.37 (16)
O5—Mn1—N3	85.41 (6)	C22—C21—C20	120.49 (19)
O4i—Mn1—N4	173.08 (6)	C22—C21—H21	119.8
O3—Mn1—N4	91.24 (5)	C20—C21—H21	119.8
O1—Mn1—N4	91.51 (6)	C21—C22—C23	121.0 (2)
O5—Mn1—N4	91.81 (5)	C21—C22—H22	119.5
N3—Mn1—N4	73.16 (6)	C23—C22—H22	119.5
C1—O1—Mn1	125.43 (13)	C24—C23—C22	120.2 (2)
C17—O3—Mn1	131.91 (12)	C24—C23—H23	119.9
C17—O4—Mn1i	135.50 (12)	C22—C23—H23	119.9
Mn1—O5—H5A	97.9 (18)	C23—C24—C25	121.04 (19)
Mn1—O5—H5B	114.8 (18)	C23—C24—H24	119.5
H5A—O5—H5B	109 (2)	C25—C24—H24	119.5
H6A—O6—H6B	109 (4)	N2—C25—C24	117.91 (16)
C10—N1—C9	118.48 (18)	N2—C25—C20	123.08 (17)
C26—N2—C25	119.27 (15)	C24—C25—C20	119.01 (18)
C33—N3—C37	118.26 (17)	N2—C26—C19	121.24 (17)
C33—N3—Mn1	126.01 (14)	N2—C26—C27	117.69 (16)
C37—N3—Mn1	115.71 (12)	C19—C26—C27	121.07 (17)
C44—N4—C41	118.01 (16)	C30—C27—C28	118.04 (19)
C44—N4—Mn1	126.95 (13)	C30—C27—C26	121.57 (17)
C41—N4—Mn1	114.80 (12)	C28—C27—C26	120.35 (19)
O2—C1—O1	125.48 (19)	C29—C28—C27	120.7 (2)
O2—C1—C2	117.87 (18)	C29—C28—H28	119.7
O1—C1—C2	116.57 (19)	C27—C28—H28	119.7
C3—C2—C4	118.27 (18)	C32—C29—C28	120.8 (2)
C3—C2—C1	118.76 (18)	C32—C29—H29	119.6
C4—C2—C1	122.91 (19)	C28—C29—H29	119.6
C2—C3—C10	121.80 (19)	C27—C30—C31	120.8 (2)
C2—C3—H3	119.1	C27—C30—H30	119.6
C10—C3—H3	119.1	C31—C30—H30	119.6
C5—C4—C9	118.26 (19)	C32—C31—C30	120.3 (3)
C5—C4—C2	125.80 (19)	C32—C31—H31	119.8
C9—C4—C2	115.9 (2)	C30—C31—H31	119.8
C6—C5—C4	121.2 (2)	C29—C32—C31	119.4 (2)
C6—C5—H5	119.4	C29—C32—H32	120.3
C4—C5—H5	119.4	C31—C32—H32	120.3
C5—C6—C7	120.1 (3)	N3—C33—C34	123.1 (2)
C5—C6—H6	119.9	N3—C33—H33	118.5
C7—C6—H6	119.9	C34—C33—H33	118.5
C8—C7—C6	120.5 (2)	C35—C34—C33	118.9 (2)
C8—C7—H7	119.8	C35—C34—H34	120.6
C6—C7—H7	119.8	C33—C34—H34	120.6
C7—C8—C9	121.1 (2)	C34—C35—C36	120.7 (2)
C7—C8—H8	119.4	C34—C35—H35	119.7
C9—C8—H8	119.4	C36—C35—H35	119.7
N1—C9—C8	117.1 (2)	C35—C36—C37	116.6 (2)
N1—C9—C4	124.13 (19)	C35—C36—C38	124.8 (2)
C8—C9—C4	118.7 (2)	C37—C36—C38	118.7 (2)
N1—C10—C3	121.3 (2)	N3—C37—C36	122.51 (19)
N1—C10—C11	117.27 (18)	N3—C37—C41	118.05 (15)
C3—C10—C11	121.37 (19)	C36—C37—C41	119.44 (18)
C14—C11—C12	118.2 (2)	C39—C38—C36	121.7 (2)
C14—C11—C10	121.5 (2)	C39—C38—H38	119.1
C12—C11—C10	120.3 (2)	C36—C38—H38	119.1
C13—C12—C11	120.1 (3)	C38—C39—C40	121.4 (2)
C13—C12—H12	120.0	C38—C39—H39	119.3
C11—C12—H12	120.0	C40—C39—H39	119.3
C16—C13—C12	121.2 (3)	C42—C40—C41	117.73 (18)
C16—C13—H13	119.4	C42—C40—C39	123.3 (2)
C12—C13—H13	119.4	C41—C40—C39	119.0 (2)
C15—C14—C11	120.7 (3)	N4—C41—C40	122.17 (18)
C15—C14—H14	119.7	N4—C41—C37	118.04 (15)
C11—C14—H14	119.7	C40—C41—C37	119.79 (17)
C16—C15—C14	120.5 (3)	C43—C42—C40	119.65 (19)
C16—C15—H15	119.8	C43—C42—H42	120.2
C14—C15—H15	119.8	C40—C42—H42	120.2
C13—C16—C15	119.3 (3)	C42—C43—C44	119.3 (2)
C13—C16—H16	120.3	C42—C43—H43	120.4
C15—C16—H16	120.3	C44—C43—H43	120.4
O4—C17—O3	125.87 (17)	N4—C44—C43	123.18 (19)
O4—C17—C18	116.12 (17)	N4—C44—H44	118.4
O3—C17—C18	117.94 (17)	C43—C44—H44	118.4

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2	0.85 (2)	1.81 (2)	2.630 (2)	161 (3)
O5—H5B···N2ii	0.83 (2)	2.04 (2)	2.868 (2)	176.
O6—H6A···O1iii	0.89 (5)	2.30 (5)	3.175 (3)	167.
O6—H6B···N1iv	0.87 (2)	2.23 (2)	3.051 (3)	157.

Table 1

Selected bond lengths (Å)

Mn1—O1	2.1740 (14)
Mn1—O3	2.1557 (15)
Mn1—O4i	2.1148 (14)
Mn1—O5	2.2358 (16)
Mn1—N3	2.2706 (16)
Mn1—N4	2.2914 (15)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O2	0.85 (2)	1.81 (2)	2.630 (2)	161 (3)
O5—H5B⋯N2ii	0.83 (2)	2.04 (2)	2.868 (2)	176
O6—H6A⋯O1iii	0.89 (5)	2.30 (5)	3.175 (3)	167
O6—H6B⋯N1iv	0.87 (2)	2.23 (2)	3.051 (3)	157

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