catena-Poly[[aqua­(4,4′-bipyridine-κ²N,N′)manganese(II)]-μ-3-(4-carboxyl­atophen­oxy)propionato-κ³O:O′,O′′]

In the crystal structure of the polymeric title compound, [Mn(C₁₀H₈N₂)(C₁₀H₈O₅)(H₂O)]_n, the Mn^II atom is O,O′-chelated by the aromatic carboxyl­ate end of the 3-(4-carboxyl­atophen­oxy)propionate dianion and is covalently bonded (through one O atom) by the aliphatic carboxyl­ate end of another dianion; it is also coordinated by a water mol­ecule. The compound adopts a helical chain structure that propagates along the c axis of the ortho­rhom­bic unit cell. The coordinated water mol­ecule engages in both intra­chain and inter­chain hydrogen bonding; the inter­chain hydrogen bonds result in a honeycomb motif. The compound crystallizes as a 0.36:0.64 inversion twin.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.033
• wR factor = 0.089
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.624     0.880
            Tmin(prime) and Tmax expected:      0.770     0.877
            RR(prime) =      0.808
            Please check that your absorption correction is appropriate.
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.360
           From the CIF: _refine_ls_abs_structure_Flack_su    0.020
PLAT033_ALERT_2_C Flack Parameter Value Deviates 2 * su from zero.       0.36
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.80
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.40 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.46
           From the CIF: _reflns_number_total               4362
           Count of symmetry unique reflns         2510
           Completeness (_total/calc)            173.78%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1852
           Fraction of Friedel pairs measured     0.738
           Are heavy atom types Z>Si present        yes
PLAT794_ALERT_5_G Check Predicted Bond Valency for Mn1         (9)       0.80
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level G
PUBL013_ALERT_1_G The _publ_section_comment (discussion of study) is
            missing. This is required for a full paper submission (but is
            optional for an electronic paper).

   0 ALERT level A = Data missing that is essential or data in wrong format
   1 ALERT level G = General alerts. Data that may be required is missing

---

Related literature

For the structure of 3-(4-carboxyphenoxy)propionic acid, see: Gao & Ng (2006). For the crystal structure of a Co^II complex with the 3-(4-carboxylatophenoxy)propionate dianion, see: Xiao et al. (2006).

S1. Experimental

Manganese dichloride hexahydrate (2 mmol), 3-(4-carboxylatophenoxy)propionic acid (2 mmol) and 2,2'-bipyridine (2 mmol) were dissolved in a 3:1 ethanol–water solution. Aqueous 0.1 M sodium hydroxide was added until the solution registered a pH of 7. The solution was set aside for the growth of crystal over several days. CH&N analysis. Calc. for C₂₀H₁₈N₂O₆Mn: C 54.93, H 4.15, N 6.41%. Found: C 54.94, H 4.13, N 6.42%.

S2. Refinement

The C-bound H atoms were placed in calculated positions [C—H = 0.93–0.97 Å and U_iso(H) = 1.2–1.5U_eq(C)], and were included in the refinement in the riding-model approximation. The water H-atoms were located in a difference Fourier map, and were refined with a distance restraint of O—H = 0.85 (1) Å; their U_iso(H) values were freely refined.

Structure description

For the structure of 3-(4-carboxyphenoxy)propionic acid, see: Gao & Ng (2006). For the crystal structure of a Co^II complex with the 3-(4-carboxylatophenoxy)propionate dianion, see: Xiao et al. (2006).

Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001) and OLEX (Dolomanov et al., 2003); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures

	Fig. 1. Part of the polymeric structure of the title compound, showing 50% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radii. Symmetry code: (i) 5/2 - x, 1 - y, z - 1/2.
	Fig. 2. Layer structure of the hydrogen-bonded network as illustrated by OLEX (Dolomanov et al., 2003).

catena-Poly[[aqua(4,4'-bipyridine-κ²N,N')manganese(II)]- µ-3-(4-carboxylatophenoxy)propionato-κ³O:O',O'']

Crystal data

[Mn(C10H8N2)(C10H8O5)(H2O)]	F(000) = 900
Mr = 437.30	Dx = 1.517 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 13538 reflections
a = 6.7770 (3) Å	θ = 3.0–27.5°
b = 16.2626 (6) Å	µ = 0.73 mm^−1
c = 17.3730 (5) Å	T = 295 K
V = 1914.71 (12) Å^3	Prism, yellow
Z = 4	0.35 × 0.29 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	4362 independent reflections
Radiation source: fine-focus sealed tube	3057 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 10.000 pixels mm^-1	θmax = 27.5°, θmin = 3.2°
ω scans	h = −8→8
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −21→21
Tmin = 0.624, Tmax = 0.880	l = −22→22
18852 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.089	w = 1/[σ^2(Fo^2) + (0.0533P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max = 0.001
4362 reflections	Δρmax = 0.34 e Å^−3
264 parameters	Δρmin = −0.30 e Å^−3
2 restraints	Absolute structure: Flack (1983), with 1860 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.36 (2)

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

	x	y	z	Uiso*/Ueq
Mn1	0.75683 (7)	0.39945 (2)	0.849961 (18)	0.03710 (11)
O1	0.8310 (3)	0.52190 (13)	0.86239 (14)	0.0622 (6)
O2	0.5582 (4)	0.59275 (14)	0.84588 (16)	0.0803 (7)
O3	0.9809 (3)	0.64933 (14)	0.98274 (10)	0.0552 (6)
O4	1.4164 (3)	0.61980 (12)	1.30356 (9)	0.0430 (4)
O5	1.6748 (3)	0.61228 (13)	1.22776 (9)	0.0459 (5)
O1W	0.4470 (3)	0.43660 (15)	0.85866 (13)	0.0520 (5)
H1W1	0.334 (2)	0.4252 (19)	0.8405 (17)	0.063 (10)*
H1W2	0.459 (9)	0.4888 (8)	0.853 (3)	0.16 (2)*
N1	0.7321 (4)	0.26198 (12)	0.86540 (11)	0.0413 (5)
N2	0.7755 (4)	0.37423 (14)	0.97641 (10)	0.0416 (5)
C1	0.7385 (5)	0.58737 (15)	0.85466 (13)	0.0463 (6)
C2	0.8625 (5)	0.66545 (18)	0.85678 (16)	0.0540 (8)
H2A	0.8992	0.6800	0.8046	0.065*
H2B	0.7827	0.7099	0.8773	0.065*
C3	1.0480 (5)	0.65767 (19)	0.90479 (14)	0.0494 (7)
H3A	1.1236	0.6098	0.8893	0.059*
H3B	1.1300	0.7062	0.8992	0.059*
C4	1.1170 (4)	0.64004 (19)	1.04023 (15)	0.0434 (8)
C5	1.3162 (4)	0.6315 (2)	1.02968 (15)	0.0447 (8)
H5	1.3696	0.6316	0.9804	0.054*
C6	1.4373 (4)	0.62257 (17)	1.09374 (14)	0.0391 (6)
H6	1.5725	0.6161	1.0868	0.047*
C7	1.3603 (4)	0.62311 (19)	1.16835 (14)	0.0360 (6)
C8	1.1573 (4)	0.6318 (2)	1.17619 (15)	0.0469 (9)
H8	1.1020	0.6323	1.2252	0.056*
C9	1.0369 (4)	0.6398 (2)	1.11337 (16)	0.0506 (8)
H9	0.9013	0.6450	1.1199	0.061*
C10	1.4908 (4)	0.61775 (16)	1.23693 (13)	0.0363 (6)
C11	0.7252 (5)	0.20784 (18)	0.80691 (16)	0.0535 (7)
H11	0.7117	0.2280	0.7571	0.064*
C12	0.7371 (6)	0.12452 (18)	0.8171 (2)	0.0664 (8)
H12	0.7305	0.0889	0.7753	0.080*
C13	0.7589 (5)	0.09507 (19)	0.8902 (2)	0.0682 (9)
H13	0.7694	0.0388	0.8986	0.082*
C14	0.7654 (5)	0.14913 (17)	0.95166 (18)	0.0583 (7)
H14	0.7786	0.1296	1.0017	0.070*
C15	0.7520 (5)	0.23271 (14)	0.93762 (14)	0.0423 (5)
C16	0.7595 (4)	0.29574 (16)	0.99965 (13)	0.0422 (6)
C17	0.7479 (5)	0.2761 (2)	1.07716 (14)	0.0574 (7)
H17	0.7367	0.2216	1.0928	0.069*
C18	0.7533 (6)	0.3384 (3)	1.13051 (15)	0.0713 (10)
H18	0.7459	0.3262	1.1827	0.086*
C19	0.7696 (5)	0.4191 (2)	1.10699 (16)	0.0672 (9)
H19	0.7728	0.4618	1.1426	0.081*
C20	0.7808 (5)	0.4344 (2)	1.02932 (15)	0.0547 (8)
H20	0.7924	0.4886	1.0128	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.03402 (19)	0.04224 (19)	0.03503 (17)	−0.0002 (2)	0.0009 (2)	0.00125 (15)
O1	0.0507 (13)	0.0422 (11)	0.0939 (16)	−0.0024 (10)	−0.0079 (12)	−0.0035 (11)
O2	0.0593 (15)	0.0597 (14)	0.122 (2)	0.0052 (12)	−0.0319 (15)	−0.0050 (15)
O3	0.0416 (12)	0.0877 (16)	0.0365 (9)	−0.0032 (11)	−0.0105 (8)	0.0006 (9)
O4	0.0323 (10)	0.0623 (12)	0.0345 (9)	−0.0020 (9)	−0.0001 (7)	−0.0047 (9)
O5	0.0272 (9)	0.0720 (13)	0.0384 (8)	−0.0008 (9)	−0.0003 (7)	−0.0006 (9)
O1W	0.0320 (11)	0.0665 (14)	0.0575 (12)	−0.0004 (10)	−0.0075 (10)	−0.0060 (11)
N1	0.0358 (12)	0.0418 (11)	0.0463 (11)	−0.0026 (12)	0.0065 (11)	0.0015 (8)
N2	0.0355 (13)	0.0551 (13)	0.0343 (10)	0.0031 (12)	−0.0014 (10)	0.0001 (9)
C1	0.0552 (16)	0.0467 (15)	0.0372 (11)	0.0002 (18)	−0.0109 (17)	0.0007 (10)
C2	0.067 (2)	0.0483 (17)	0.0465 (15)	−0.0065 (15)	−0.0132 (16)	0.0111 (14)
C3	0.0527 (18)	0.0541 (18)	0.0415 (14)	−0.0061 (15)	−0.0048 (13)	0.0042 (13)
C4	0.0365 (16)	0.053 (2)	0.0410 (15)	−0.0059 (14)	−0.0084 (12)	−0.0012 (13)
C5	0.0441 (18)	0.0559 (19)	0.0340 (13)	−0.0014 (13)	0.0012 (11)	−0.0039 (12)
C6	0.0301 (14)	0.0441 (17)	0.0430 (14)	0.0004 (12)	−0.0002 (11)	−0.0040 (13)
C7	0.0324 (14)	0.0366 (15)	0.0390 (14)	−0.0029 (12)	−0.0028 (10)	−0.0005 (12)
C8	0.0320 (15)	0.072 (2)	0.0369 (14)	−0.0050 (15)	0.0030 (12)	0.0040 (14)
C9	0.0287 (15)	0.078 (2)	0.0450 (15)	−0.0031 (14)	0.0005 (12)	0.0018 (15)
C10	0.0331 (14)	0.0375 (14)	0.0382 (13)	−0.0027 (11)	−0.0006 (11)	−0.0020 (11)
C11	0.052 (2)	0.0538 (16)	0.0549 (15)	−0.0053 (17)	0.0077 (16)	−0.0043 (13)
C12	0.058 (2)	0.0512 (17)	0.090 (2)	−0.008 (2)	0.009 (2)	−0.0167 (16)
C13	0.0519 (18)	0.0401 (15)	0.113 (3)	−0.001 (2)	0.007 (2)	0.0007 (16)
C14	0.0363 (16)	0.0584 (18)	0.0803 (19)	0.0010 (19)	−0.0009 (18)	0.0230 (15)
C15	0.0232 (11)	0.0463 (14)	0.0574 (14)	0.0021 (16)	0.0056 (16)	0.0111 (11)
C16	0.0206 (11)	0.0627 (15)	0.0433 (12)	0.0054 (17)	0.0015 (14)	0.0114 (11)
C17	0.0384 (15)	0.086 (2)	0.0478 (14)	0.004 (2)	0.0042 (16)	0.0209 (14)
C18	0.0448 (17)	0.133 (3)	0.0355 (13)	0.007 (3)	0.0048 (16)	0.0119 (17)
C19	0.049 (2)	0.109 (3)	0.0435 (15)	0.004 (2)	0.0008 (17)	−0.0165 (16)
C20	0.049 (2)	0.0719 (18)	0.0436 (14)	0.0053 (17)	−0.0027 (14)	−0.0088 (13)

Geometric parameters (Å, º)

Mn1—O1	2.065 (2)	C5—C6	1.391 (4)
Mn1—O5^i	2.181 (2)	C5—H5	0.93
Mn1—O1W	2.190 (2)	C6—C7	1.398 (3)
Mn1—N2	2.2384 (18)	C6—H6	0.93
Mn1—N1	2.258 (2)	C7—C8	1.390 (4)
Mn1—O4^i	2.377 (2)	C7—C10	1.487 (3)
Mn1—C10^i	2.619 (2)	C8—C9	1.368 (4)
O1—C1	1.243 (3)	C8—H8	0.93
O2—C1	1.234 (4)	C9—H9	0.93
O3—C4	1.368 (3)	C10—Mn1^ii	2.619 (2)
O3—C3	1.435 (3)	C11—C12	1.369 (4)
O4—C10	1.263 (3)	C11—H11	0.93
O5—C10	1.260 (3)	C12—C13	1.365 (5)
O1W—H1W1	0.85 (1)	C12—H12	0.93
O1W—H1W2	0.86 (1)	C13—C14	1.384 (5)
N1—C11	1.345 (3)	C13—H13	0.93
N1—C15	1.349 (3)	C14—C15	1.384 (4)
N2—C16	1.343 (3)	C14—H14	0.93
N2—C20	1.343 (3)	C15—C16	1.488 (4)
C1—C2	1.523 (4)	C16—C17	1.386 (3)
C2—C3	1.514 (4)	C17—C18	1.375 (5)
C2—H2A	0.97	C17—H17	0.93
C2—H2B	0.97	C18—C19	1.378 (5)
C3—H3A	0.97	C18—H18	0.93
C3—H3B	0.97	C19—C20	1.374 (4)
C4—C5	1.369 (4)	C19—H19	0.93
C4—C9	1.382 (4)	C20—H20	0.93
O1—Mn1—O5^i	97.72 (9)	C4—C5—C6	119.0 (3)
O1—Mn1—O1W	87.71 (9)	C4—C5—H5	120.5
O5^i—Mn1—O1W	107.15 (8)	C6—C5—H5	120.5
O1—Mn1—N2	93.46 (9)	C5—C6—C7	121.4 (3)
O5^i—Mn1—N2	158.00 (8)	C5—C6—H6	119.3
O1W—Mn1—N2	92.12 (9)	C7—C6—H6	119.3
O1—Mn1—N1	163.82 (9)	C8—C7—C6	117.5 (3)
O5^i—Mn1—N1	92.57 (8)	C8—C7—C10	121.1 (3)
O1W—Mn1—N1	101.18 (9)	C6—C7—C10	121.4 (3)
N2—Mn1—N1	72.91 (8)	C9—C8—C7	121.4 (3)
O1—Mn1—O4^i	86.31 (8)	C9—C8—H8	119.3
O5^i—Mn1—O4^i	57.36 (6)	C7—C8—H8	119.3
O1W—Mn1—O4^i	162.32 (7)	C8—C9—C4	120.0 (3)
N2—Mn1—O4^i	104.83 (7)	C8—C9—H9	120.0
N1—Mn1—O4^i	88.80 (8)	C4—C9—H9	120.0
O1—Mn1—C10^i	91.29 (9)	O5—C10—O4	120.8 (2)
O5^i—Mn1—C10^i	28.63 (7)	O5—C10—C7	119.4 (2)
O1W—Mn1—C10^i	135.01 (8)	O4—C10—C7	119.7 (2)
N2—Mn1—C10^i	132.79 (8)	O5—C10—Mn1^ii	56.02 (12)
N1—Mn1—C10^i	91.82 (8)	O4—C10—Mn1^ii	64.93 (12)
O4^i—Mn1—C10^i	28.76 (6)	C7—C10—Mn1^ii	174.76 (19)
C1—O1—Mn1	133.8 (2)	N1—C11—C12	123.3 (3)
C4—O3—C3	119.1 (2)	N1—C11—H11	118.4
C10—O4—Mn1^ii	86.31 (14)	C12—C11—H11	118.4
C10—O5—Mn1^ii	95.35 (15)	C11—C12—C13	118.3 (3)
Mn1—O1W—H1W1	141 (2)	C11—C12—H12	120.9
Mn1—O1W—H1W2	100 (4)	C13—C12—H12	120.9
H1W1—O1W—H1W2	105 (5)	C12—C13—C14	119.9 (3)
C11—N1—C15	118.4 (2)	C12—C13—H13	120.1
C11—N1—Mn1	124.11 (18)	C14—C13—H13	120.1
C15—N1—Mn1	116.90 (16)	C13—C14—C15	119.1 (3)
C16—N2—C20	119.3 (2)	C13—C14—H14	120.5
C16—N2—Mn1	117.68 (15)	C15—C14—H14	120.5
C20—N2—Mn1	122.65 (19)	N1—C15—C14	121.1 (2)
O2—C1—O1	125.0 (3)	N1—C15—C16	115.7 (2)
O2—C1—C2	119.3 (3)	C14—C15—C16	123.1 (2)
O1—C1—C2	115.7 (3)	N2—C16—C17	121.1 (2)
C3—C2—C1	113.7 (2)	N2—C16—C15	116.09 (19)
C3—C2—H2A	108.8	C17—C16—C15	122.8 (2)
C1—C2—H2A	108.8	C18—C17—C16	118.9 (3)
C3—C2—H2B	108.8	C18—C17—H17	120.6
C1—C2—H2B	108.8	C16—C17—H17	120.6
H2A—C2—H2B	107.7	C17—C18—C19	120.3 (3)
O3—C3—C2	105.4 (2)	C17—C18—H18	119.8
O3—C3—H3A	110.7	C19—C18—H18	119.8
C2—C3—H3A	110.7	C20—C19—C18	117.9 (3)
O3—C3—H3B	110.7	C20—C19—H19	121.0
C2—C3—H3B	110.7	C18—C19—H19	121.0
H3A—C3—H3B	108.8	N2—C20—C19	122.5 (3)
C5—C4—O3	125.3 (3)	N2—C20—H20	118.7
C5—C4—C9	120.7 (3)	C19—C20—H20	118.7
O3—C4—C9	114.0 (3)
O5^i—Mn1—O1—C1	88.7 (3)	C5—C6—C7—C8	0.8 (5)
O1W—Mn1—O1—C1	−18.3 (3)	C5—C6—C7—C10	−176.9 (3)
N2—Mn1—O1—C1	−110.3 (3)	C6—C7—C8—C9	−0.1 (6)
N1—Mn1—O1—C1	−142.3 (3)	C10—C7—C8—C9	177.6 (3)
O4^i—Mn1—O1—C1	145.1 (3)	C7—C8—C9—C4	−0.7 (6)
C10^i—Mn1—O1—C1	116.7 (3)	C5—C4—C9—C8	0.7 (5)
O1—Mn1—N1—C11	−141.2 (3)	O3—C4—C9—C8	−179.3 (3)
O5^i—Mn1—N1—C11	−11.6 (3)	Mn1^ii—O5—C10—O4	4.0 (3)
O1W—Mn1—N1—C11	96.4 (3)	Mn1^ii—O5—C10—C7	−176.9 (2)
N2—Mn1—N1—C11	−174.8 (3)	Mn1^ii—O4—C10—O5	−3.7 (3)
O4^i—Mn1—N1—C11	−68.9 (3)	Mn1^ii—O4—C10—C7	177.2 (2)
C10^i—Mn1—N1—C11	−40.3 (3)	C8—C7—C10—O5	−177.9 (3)
O1—Mn1—N1—C15	29.6 (5)	C6—C7—C10—O5	−0.3 (4)
O5^i—Mn1—N1—C15	159.2 (2)	C8—C7—C10—O4	1.2 (5)
O1W—Mn1—N1—C15	−92.7 (2)	C6—C7—C10—O4	178.8 (3)
N2—Mn1—N1—C15	−3.9 (2)	C15—N1—C11—C12	0.1 (5)
O4^i—Mn1—N1—C15	102.0 (2)	Mn1—N1—C11—C12	170.9 (3)
C10^i—Mn1—N1—C15	130.6 (2)	N1—C11—C12—C13	−0.6 (6)
O1—Mn1—N2—C16	−172.6 (2)	C11—C12—C13—C14	1.0 (6)
O5^i—Mn1—N2—C16	−52.0 (4)	C12—C13—C14—C15	−0.8 (6)
O1W—Mn1—N2—C16	99.5 (2)	C11—N1—C15—C14	0.1 (5)
N1—Mn1—N2—C16	−1.5 (2)	Mn1—N1—C15—C14	−171.3 (3)
O4^i—Mn1—N2—C16	−85.5 (2)	C11—N1—C15—C16	179.8 (3)
C10^i—Mn1—N2—C16	−77.7 (2)	Mn1—N1—C15—C16	8.3 (4)
O1—Mn1—N2—C20	14.6 (2)	C13—C14—C15—N1	0.3 (5)
O5^i—Mn1—N2—C20	135.2 (2)	C13—C14—C15—C16	−179.4 (3)
O1W—Mn1—N2—C20	−73.2 (2)	C20—N2—C16—C17	0.1 (5)
N1—Mn1—N2—C20	−174.3 (3)	Mn1—N2—C16—C17	−172.9 (2)
O4^i—Mn1—N2—C20	101.7 (2)	C20—N2—C16—C15	179.2 (3)
C10^i—Mn1—N2—C20	109.6 (2)	Mn1—N2—C16—C15	6.2 (4)
Mn1—O1—C1—O2	10.1 (5)	N1—C15—C16—N2	−9.7 (4)
Mn1—O1—C1—C2	−170.1 (2)	C14—C15—C16—N2	170.0 (3)
O2—C1—C2—C3	151.1 (3)	N1—C15—C16—C17	169.4 (3)
O1—C1—C2—C3	−28.7 (3)	C14—C15—C16—C17	−10.9 (5)
C4—O3—C3—C2	179.2 (2)	N2—C16—C17—C18	−0.1 (5)
C1—C2—C3—O3	−67.6 (3)	C15—C16—C17—C18	−179.1 (3)
C3—O3—C4—C5	−5.4 (5)	C16—C17—C18—C19	0.1 (6)
C3—O3—C4—C9	174.7 (3)	C17—C18—C19—C20	−0.2 (6)
O3—C4—C5—C6	180.0 (3)	C16—N2—C20—C19	−0.3 (5)
C9—C4—C5—C6	−0.1 (5)	Mn1—N2—C20—C19	172.4 (2)
C4—C5—C6—C7	−0.7 (5)	C18—C19—C20—N2	0.3 (5)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W2···O2	0.86 (1)	1.82 (2)	2.658 (3)	164 (6)
O1W—H1W1···O4^iii	0.85 (1)	1.96 (1)	2.797 (3)	170 (3)

Symmetry code: (iii) −x+3/2, −y+1, z−1/2.