Aqua­chloridobis(2-{[3-(morpholin-4-yl)prop­yl]imino­meth­yl}phenolato)manganese(III) monohydrate

Ikmal Hisham, N.A.; Khaledi, H.; Mohd Ali, H.

doi:10.1107/S1600536811026493

Aquachloridobis(2-{[3-(morpholin-4-yl)propyl]iminomethyl}phenolato)manganese(III) monohydrate

N. A. Ikmal Hisham, H. Khaledi and H. Mohd Ali

In the title compound, [Mn(C₁₄H₁₉N₂O₂)₂Cl(H₂O)]·H₂O, the Mn^III atom is N,O-chelated by two monoanionic Schiff bases, forming two six-membered chelate rings. One Cl atom and one water molecule in trans positions complete a distorted octahedral geometry around the metal atom. In the crystal, the complex molecules and the uncoordinated water molecules are connected via O—H

N, O—H

O and O—H

Cl hydrogen bonds into layers parallel to the ac plane and these are consolidated by C—H

π interactions. The layers are further linked into a three-dimensional network through C—H

O interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811026493/is2745sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536811026493/is2745Isup2.hkl Contains datablock I

CCDC reference: 841007

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.039
wR factor = 0.093
Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          2
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         10
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         10

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          6
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          4

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

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

Comment top

The title Mn^III complex was obtained through the reaction of the Schiff base, prepared in situ, and Mn(II) chloride. Under the reaction conditions, Mn^II ion was oxidized to Mn^III and N,O-chelated by two deprotonated Schiff base ligands. Similar to what was observed in a Zn(II) complex of the same Schiff base (Ikmal Hisham et al., 2011), the ligand applies only its phenolate oxygen and imine nitrogen atoms in the coordination, while its morpholine nitrogen atom stays away from coordination. One chlorine atom and one molecule of water complete the distorted octahedral coordination environment. The Mn—N, Mn—O and Mn—Cl interatomic distances are comparable to the values reported for a similar structure (Huang et al., 2004). In the crystal, the Mn^III complexes and the hydration water molecules are hydrogen bonded together through O—H···N, O—H···O and O—H···Cl interactions, forming two-dimensional arrays parallel to the ac plane. The structure of the layers is supplemented by C—H···π interactions (Table 1). The layers are further linked into a three-dimensional network via C—H···O interactions.

Related literature top

For the structure of a Zn^II complex of the same Schiff base, see: Ikmal Hisham et al. (2011). For the structure of a similar Mn^III complex, see: Huang et al. (2004).

Experimental top

A mixture of salicylaldehyde (0.20 g, 1.64 mmol) and N-(3-aminopropyl)morpholine (0.24 g, 1.64 mmol) in ethanol (20 ml) was refluxed for 2 hr followed by addition of a solution of manganese(II) chloride (0.21 g, 1.64 mmol) in a minimum amount of water. The resulting solution was stirred for 2 hr at room temperature and then set aside. The crystals of the title complex were obtained after one week

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at 50° probability level. The C-bound Hydrogen atoms have been omitted for clarity.

Aquachloridobis(2-{[3-(morpholin-4- yl)propyl]iminomethyl}phenolato)manganese(III) monohydrate top

Crystal data top

[Mn(C₁₄H₁₉N₂O₂)₂Cl(H₂O)]·H₂O	Z = 2
M_r = 621.05	F(000) = 656
Triclinic, P1	D_x = 1.402 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4831 (2) Å	Cell parameters from 3220 reflections
b = 12.4169 (3) Å	θ = 2.2–28.9°
c = 12.9518 (3) Å	µ = 0.59 mm⁻¹
α = 95.540 (1)°	T = 100 K
β = 90.306 (2)°	Plate, blue
γ = 104.229 (1)°	0.20 × 0.16 × 0.04 mm
V = 1470.72 (6) Å³

Data collection top

Bruker APEXII CCD diffractometer	6393 independent reflections
Radiation source: fine-focus sealed tube	4740 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 27.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.892, T_max = 0.977	k = −15→15
13272 measured reflections	l = −16→16

Refinement top

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) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0463P)²] where P = (F_o² + 2F_c²)/3
6393 reflections	(Δ/σ)_max = 0.001
373 parameters	Δρ_max = 0.43 e Å⁻³
4 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Mn(C₁₄H₁₉N₂O₂)₂Cl(H₂O)]·H₂O	γ = 104.229 (1)°
M_r = 621.05	V = 1470.72 (6) Å³
Triclinic, P1	Z = 2
a = 9.4831 (2) Å	Mo Kα radiation
b = 12.4169 (3) Å	µ = 0.59 mm⁻¹
c = 12.9518 (3) Å	T = 100 K
α = 95.540 (1)°	0.20 × 0.16 × 0.04 mm
β = 90.306 (2)°

Data collection top

Bruker APEXII CCD diffractometer	6393 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4740 reflections with I > 2σ(I)
T_min = 0.892, T_max = 0.977	R_int = 0.034
13272 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	4 restraints
wR(F²) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.43 e Å⁻³
6393 reflections	Δρ_min = −0.32 e Å⁻³
373 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Mn1	0.80758 (3)	0.51790 (3)	0.25109 (2)	0.00991 (9)
Cl1	1.07112 (5)	0.49604 (5)	0.24934 (4)	0.01422 (12)
O1	0.88326 (15)	0.67047 (12)	0.29100 (11)	0.0120 (3)
O2	0.37546 (17)	0.08392 (13)	0.79286 (12)	0.0206 (4)
O3	0.73429 (16)	0.36491 (12)	0.21182 (11)	0.0132 (3)
O4	0.71302 (17)	0.94441 (14)	−0.31588 (12)	0.0229 (4)
O5	0.58953 (16)	0.55756 (13)	0.24999 (12)	0.0136 (3)
H5A	0.511 (2)	0.5122 (18)	0.2587 (19)	0.020*
H5B	0.585 (3)	0.6146 (16)	0.2859 (17)	0.020*
N1	0.77786 (18)	0.49029 (14)	0.40365 (13)	0.0107 (4)
N2	0.45557 (18)	0.24065 (15)	0.64027 (13)	0.0118 (4)
N3	0.81100 (18)	0.54400 (15)	0.09684 (13)	0.0118 (4)
N4	0.71767 (19)	0.80497 (15)	−0.15371 (14)	0.0136 (4)
C1	0.9646 (2)	0.71444 (18)	0.37568 (16)	0.0112 (4)
C2	1.0615 (2)	0.81922 (18)	0.37504 (16)	0.0139 (5)
H2	1.0708	0.8558	0.3134	0.017*
C3	1.1439 (2)	0.87054 (19)	0.46231 (17)	0.0153 (5)
H3	1.2097	0.9415	0.4597	0.018*
C4	1.1319 (2)	0.81970 (19)	0.55433 (17)	0.0155 (5)
H4	1.1888	0.8555	0.6142	0.019*
C5	1.0359 (2)	0.71650 (18)	0.55720 (16)	0.0134 (4)
H5	1.0261	0.6819	0.6199	0.016*
C6	0.9528 (2)	0.66207 (18)	0.46865 (16)	0.0113 (4)
C7	0.8498 (2)	0.55633 (18)	0.47924 (16)	0.0121 (4)
H7	0.8341	0.5340	0.5472	0.015*
C8	0.6650 (2)	0.39039 (18)	0.42446 (16)	0.0130 (4)
H8A	0.6932	0.3242	0.3906	0.016*
H8B	0.5731	0.3941	0.3900	0.016*
C9	0.6333 (2)	0.37064 (18)	0.53695 (16)	0.0137 (5)
H9A	0.6052	0.4355	0.5737	0.016*
H9B	0.7209	0.3601	0.5726	0.016*
C10	0.5093 (2)	0.26629 (18)	0.53680 (16)	0.0138 (5)
H10A	0.4274	0.2753	0.4935	0.017*
H10B	0.5425	0.2018	0.5039	0.017*
C11	0.5658 (2)	0.20893 (19)	0.70355 (17)	0.0155 (5)
H11A	0.6521	0.2728	0.7163	0.019*
H11B	0.5971	0.1460	0.6659	0.019*
C12	0.5019 (2)	0.1749 (2)	0.80625 (17)	0.0192 (5)
H12A	0.5764	0.1534	0.8481	0.023*
H12B	0.4762	0.2397	0.8451	0.023*
C13	0.2678 (2)	0.11214 (19)	0.73002 (17)	0.0164 (5)
H13A	0.2352	0.1750	0.7668	0.020*
H13B	0.1824	0.0474	0.7187	0.020*
C14	0.3271 (2)	0.14476 (19)	0.62656 (17)	0.0152 (5)
H14A	0.3544	0.0805	0.5879	0.018*
H14B	0.2507	0.1645	0.5852	0.018*
C15	0.7750 (2)	0.30723 (18)	0.13036 (16)	0.0114 (4)
C16	0.7705 (2)	0.19455 (18)	0.13548 (16)	0.0133 (5)
H16	0.7444	0.1618	0.1982	0.016*
C17	0.8037 (2)	0.13013 (19)	0.05026 (17)	0.0169 (5)
H17	0.8005	0.0538	0.0553	0.020*
C18	0.8416 (2)	0.17592 (19)	−0.04295 (17)	0.0169 (5)
H18	0.8638	0.1311	−0.1013	0.020*
C19	0.8466 (2)	0.28655 (19)	−0.04938 (16)	0.0149 (5)
H19	0.8713	0.3177	−0.1130	0.018*
C20	0.8160 (2)	0.35454 (18)	0.03621 (16)	0.0119 (4)
C21	0.8181 (2)	0.46903 (18)	0.02342 (16)	0.0127 (4)
H21	0.8255	0.4905	−0.0452	0.015*
C22	0.7958 (2)	0.65460 (18)	0.07310 (16)	0.0146 (5)
H22A	0.8813	0.7115	0.1043	0.018*
H22B	0.7088	0.6688	0.1084	0.018*
C23	0.7820 (2)	0.67320 (18)	−0.03982 (16)	0.0152 (5)
H23A	0.7043	0.6123	−0.0753	0.018*
H23B	0.8747	0.6728	−0.0746	0.018*
C24	0.7455 (3)	0.78488 (19)	−0.04681 (17)	0.0189 (5)
H24A	0.6583	0.7872	−0.0057	0.023*
H24B	0.8273	0.8455	−0.0159	0.023*
C25	0.8518 (2)	0.85933 (19)	−0.20428 (17)	0.0179 (5)
H25A	0.9215	0.8115	−0.2056	0.022*
H25B	0.8980	0.9317	−0.1644	0.022*
C26	0.8160 (2)	0.8783 (2)	−0.31383 (18)	0.0206 (5)
H26A	0.9063	0.9162	−0.3467	0.025*
H26B	0.7762	0.8053	−0.3546	0.025*
C27	0.5831 (2)	0.8915 (2)	−0.26777 (17)	0.0184 (5)
H27A	0.5393	0.8184	−0.3071	0.022*
H27B	0.5122	0.9382	−0.2693	0.022*
C28	0.6134 (2)	0.87446 (18)	−0.15698 (17)	0.0149 (5)
H28A	0.6536	0.9477	−0.1167	0.018*
H28B	0.5216	0.8377	−0.1252	0.018*
O6	0.34610 (17)	0.39900 (13)	0.28380 (12)	0.0158 (3)
H6A	0.274 (2)	0.426 (2)	0.2761 (19)	0.024*
H6B	0.339 (3)	0.3387 (16)	0.2441 (17)	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.01027 (17)	0.01079 (18)	0.00858 (17)	0.00230 (13)	0.00173 (12)	0.00125 (12)
Cl1	0.0121 (2)	0.0199 (3)	0.0121 (3)	0.0063 (2)	0.00197 (19)	0.0027 (2)
O1	0.0125 (7)	0.0103 (8)	0.0118 (8)	0.0000 (6)	−0.0014 (6)	0.0014 (6)
O2	0.0196 (8)	0.0183 (9)	0.0260 (9)	0.0054 (7)	0.0063 (7)	0.0107 (7)
O3	0.0172 (8)	0.0118 (8)	0.0102 (8)	0.0025 (7)	0.0046 (6)	0.0014 (6)
O4	0.0211 (9)	0.0252 (10)	0.0267 (10)	0.0090 (8)	0.0071 (7)	0.0144 (7)
O5	0.0113 (7)	0.0135 (9)	0.0149 (8)	0.0017 (7)	0.0026 (6)	−0.0005 (6)
N1	0.0104 (9)	0.0103 (9)	0.0123 (9)	0.0034 (7)	0.0025 (7)	0.0028 (7)
N2	0.0099 (9)	0.0129 (9)	0.0114 (9)	−0.0004 (7)	0.0034 (7)	0.0026 (7)
N3	0.0104 (9)	0.0125 (9)	0.0130 (9)	0.0039 (8)	0.0022 (7)	0.0015 (7)
N4	0.0144 (9)	0.0146 (10)	0.0132 (9)	0.0055 (8)	0.0018 (7)	0.0034 (7)
C1	0.0093 (10)	0.0147 (11)	0.0112 (11)	0.0065 (9)	0.0019 (8)	−0.0009 (8)
C2	0.0146 (11)	0.0143 (12)	0.0127 (11)	0.0029 (9)	0.0035 (9)	0.0038 (9)
C3	0.0116 (10)	0.0130 (11)	0.0195 (12)	0.0004 (9)	0.0017 (9)	−0.0006 (9)
C4	0.0154 (11)	0.0171 (12)	0.0126 (11)	0.0030 (10)	−0.0021 (9)	−0.0029 (9)
C5	0.0145 (11)	0.0143 (11)	0.0114 (11)	0.0038 (9)	0.0017 (8)	0.0018 (9)
C6	0.0092 (10)	0.0144 (11)	0.0112 (11)	0.0051 (9)	0.0026 (8)	0.0008 (8)
C7	0.0122 (10)	0.0150 (11)	0.0108 (11)	0.0060 (9)	0.0022 (8)	0.0029 (9)
C8	0.0116 (10)	0.0145 (11)	0.0120 (11)	0.0009 (9)	0.0003 (8)	0.0028 (9)
C9	0.0141 (11)	0.0149 (12)	0.0118 (11)	0.0024 (9)	0.0033 (8)	0.0029 (9)
C10	0.0140 (11)	0.0149 (12)	0.0110 (11)	0.0004 (9)	0.0031 (8)	0.0026 (9)
C11	0.0106 (10)	0.0199 (12)	0.0165 (12)	0.0033 (9)	0.0031 (8)	0.0062 (9)
C12	0.0150 (11)	0.0259 (13)	0.0183 (12)	0.0054 (10)	0.0016 (9)	0.0081 (10)
C13	0.0141 (11)	0.0149 (12)	0.0204 (12)	0.0038 (9)	0.0050 (9)	0.0023 (9)
C14	0.0131 (11)	0.0142 (11)	0.0161 (12)	0.0001 (9)	0.0023 (9)	−0.0013 (9)
C15	0.0073 (10)	0.0134 (11)	0.0116 (11)	0.0005 (9)	−0.0015 (8)	−0.0026 (8)
C16	0.0119 (10)	0.0154 (12)	0.0121 (11)	0.0017 (9)	0.0006 (8)	0.0031 (9)
C17	0.0159 (11)	0.0145 (12)	0.0198 (12)	0.0036 (9)	−0.0007 (9)	−0.0005 (9)
C18	0.0185 (11)	0.0166 (12)	0.0149 (12)	0.0048 (10)	0.0021 (9)	−0.0027 (9)
C19	0.0156 (11)	0.0177 (12)	0.0108 (11)	0.0034 (10)	0.0009 (8)	0.0001 (9)
C20	0.0107 (10)	0.0127 (11)	0.0117 (11)	0.0018 (9)	0.0002 (8)	0.0014 (8)
C21	0.0107 (10)	0.0164 (12)	0.0105 (11)	0.0021 (9)	0.0018 (8)	0.0026 (9)
C22	0.0178 (11)	0.0146 (12)	0.0129 (11)	0.0061 (10)	0.0031 (9)	0.0031 (9)
C23	0.0180 (11)	0.0165 (12)	0.0117 (11)	0.0054 (10)	−0.0017 (9)	0.0007 (9)
C24	0.0258 (13)	0.0193 (13)	0.0137 (12)	0.0093 (11)	−0.0006 (9)	0.0026 (9)
C25	0.0153 (11)	0.0167 (12)	0.0221 (13)	0.0049 (10)	0.0012 (9)	0.0013 (10)
C26	0.0180 (12)	0.0233 (13)	0.0230 (13)	0.0062 (10)	0.0062 (10)	0.0106 (10)
C27	0.0168 (11)	0.0202 (13)	0.0191 (12)	0.0051 (10)	0.0010 (9)	0.0051 (10)
C28	0.0131 (11)	0.0127 (11)	0.0186 (12)	0.0031 (9)	0.0001 (9)	0.0008 (9)
O6	0.0141 (8)	0.0135 (9)	0.0199 (9)	0.0046 (7)	−0.0012 (7)	−0.0014 (7)

Geometric parameters (Å, º) top

Mn1—O1	1.8735 (15)	C10—H10B	0.9900
Mn1—O3	1.8738 (15)	C11—C12	1.519 (3)
Mn1—N1	2.0471 (17)	C11—H11A	0.9900
Mn1—N3	2.0537 (17)	C11—H11B	0.9900
Mn1—O5	2.2406 (15)	C12—H12A	0.9900
Mn1—Cl1	2.5793 (6)	C12—H12B	0.9900
O1—C1	1.328 (2)	C13—C14	1.509 (3)
O2—C12	1.428 (3)	C13—H13A	0.9900
O2—C13	1.431 (3)	C13—H13B	0.9900
O3—C15	1.330 (2)	C14—H14A	0.9900
O4—C26	1.423 (3)	C14—H14B	0.9900
O4—C27	1.424 (3)	C15—C16	1.397 (3)
O5—H5A	0.829 (16)	C15—C20	1.419 (3)
O5—H5B	0.819 (16)	C16—C17	1.383 (3)
N1—C7	1.288 (3)	C16—H16	0.9500
N1—C8	1.474 (3)	C17—C18	1.395 (3)
N2—C10	1.472 (2)	C17—H17	0.9500
N2—C11	1.475 (3)	C18—C19	1.373 (3)
N2—C14	1.476 (3)	C18—H18	0.9500
N3—C21	1.279 (3)	C19—C20	1.403 (3)
N3—C22	1.476 (3)	C19—H19	0.9500
N4—C24	1.464 (3)	C20—C21	1.442 (3)
N4—C28	1.466 (3)	C21—H21	0.9500
N4—C25	1.475 (3)	C22—C23	1.512 (3)
C1—C2	1.397 (3)	C22—H22A	0.9900
C1—C6	1.415 (3)	C22—H22B	0.9900
C2—C3	1.379 (3)	C23—C24	1.520 (3)
C2—H2	0.9500	C23—H23A	0.9900
C3—C4	1.394 (3)	C23—H23B	0.9900
C3—H3	0.9500	C24—H24A	0.9900
C4—C5	1.381 (3)	C24—H24B	0.9900
C4—H4	0.9500	C25—C26	1.511 (3)
C5—C6	1.404 (3)	C25—H25A	0.9900
C5—H5	0.9500	C25—H25B	0.9900
C6—C7	1.450 (3)	C26—H26A	0.9900
C7—H7	0.9500	C26—H26B	0.9900
C8—C9	1.520 (3)	C27—C28	1.507 (3)
C8—H8A	0.9900	C27—H27A	0.9900
C8—H8B	0.9900	C27—H27B	0.9900
C9—C10	1.521 (3)	C28—H28A	0.9900
C9—H9A	0.9900	C28—H28B	0.9900
C9—H9B	0.9900	O6—H6A	0.840 (16)
C10—H10A	0.9900	O6—H6B	0.855 (16)

O1—Mn1—O3	179.21 (7)	C11—C12—H12A	109.1
O1—Mn1—N1	89.85 (7)	O2—C12—H12B	109.1
O3—Mn1—N1	89.94 (7)	C11—C12—H12B	109.1
O1—Mn1—N3	91.65 (7)	H12A—C12—H12B	107.9
O3—Mn1—N3	88.65 (7)	O2—C13—C14	111.31 (17)
N1—Mn1—N3	173.12 (7)	O2—C13—H13A	109.4
O1—Mn1—O5	85.88 (6)	C14—C13—H13A	109.4
O3—Mn1—O5	94.87 (6)	O2—C13—H13B	109.4
N1—Mn1—O5	87.84 (6)	C14—C13—H13B	109.4
N3—Mn1—O5	85.57 (6)	H13A—C13—H13B	108.0
O1—Mn1—Cl1	88.07 (5)	N2—C14—C13	111.01 (18)
O3—Mn1—Cl1	91.19 (5)	N2—C14—H14A	109.4
N1—Mn1—Cl1	94.78 (5)	C13—C14—H14A	109.4
N3—Mn1—Cl1	91.99 (5)	N2—C14—H14B	109.4
O5—Mn1—Cl1	173.41 (4)	C13—C14—H14B	109.4
C1—O1—Mn1	126.07 (13)	H14A—C14—H14B	108.0
C12—O2—C13	110.02 (16)	O3—C15—C16	119.06 (18)
C15—O3—Mn1	125.73 (13)	O3—C15—C20	122.30 (19)
C26—O4—C27	109.95 (17)	C16—C15—C20	118.56 (18)
Mn1—O5—H5A	124.5 (17)	C17—C16—C15	120.7 (2)
Mn1—O5—H5B	115.0 (18)	C17—C16—H16	119.6
H5A—O5—H5B	105 (2)	C15—C16—H16	119.6
C7—N1—C8	120.36 (18)	C16—C17—C18	120.8 (2)
C7—N1—Mn1	123.24 (15)	C16—C17—H17	119.6
C8—N1—Mn1	116.38 (13)	C18—C17—H17	119.6
C10—N2—C11	111.46 (16)	C19—C18—C17	119.2 (2)
C10—N2—C14	108.09 (16)	C19—C18—H18	120.4
C11—N2—C14	107.89 (17)	C17—C18—H18	120.4
C21—N3—C22	120.34 (18)	C18—C19—C20	121.3 (2)
C21—N3—Mn1	123.59 (15)	C18—C19—H19	119.4
C22—N3—Mn1	115.98 (13)	C20—C19—H19	119.4
C24—N4—C28	110.73 (16)	C19—C20—C15	119.3 (2)
C24—N4—C25	112.32 (17)	C19—C20—C21	118.59 (19)
C28—N4—C25	108.87 (17)	C15—C20—C21	121.96 (18)
O1—C1—C2	118.93 (19)	N3—C21—C20	125.36 (19)
O1—C1—C6	122.81 (19)	N3—C21—H21	117.3
C2—C1—C6	118.19 (19)	C20—C21—H21	117.3
C3—C2—C1	121.2 (2)	N3—C22—C23	117.68 (17)
C3—C2—H2	119.4	N3—C22—H22A	107.9
C1—C2—H2	119.4	C23—C22—H22A	107.9
C2—C3—C4	120.9 (2)	N3—C22—H22B	107.9
C2—C3—H3	119.6	C23—C22—H22B	107.9
C4—C3—H3	119.6	H22A—C22—H22B	107.2
C5—C4—C3	119.1 (2)	C22—C23—C24	109.22 (17)
C5—C4—H4	120.5	C22—C23—H23A	109.8
C3—C4—H4	120.5	C24—C23—H23A	109.8
C4—C5—C6	120.9 (2)	C22—C23—H23B	109.8
C4—C5—H5	119.5	C24—C23—H23B	109.8
C6—C5—H5	119.5	H23A—C23—H23B	108.3
C5—C6—C1	119.8 (2)	N4—C24—C23	112.68 (17)
C5—C6—C7	117.55 (19)	N4—C24—H24A	109.1
C1—C6—C7	122.54 (19)	C23—C24—H24A	109.1
N1—C7—C6	125.10 (19)	N4—C24—H24B	109.1
N1—C7—H7	117.5	C23—C24—H24B	109.1
C6—C7—H7	117.5	H24A—C24—H24B	107.8
N1—C8—C9	117.99 (18)	N4—C25—C26	109.81 (18)
N1—C8—H8A	107.8	N4—C25—H25A	109.7
C9—C8—H8A	107.8	C26—C25—H25A	109.7
N1—C8—H8B	107.8	N4—C25—H25B	109.7
C9—C8—H8B	107.8	C26—C25—H25B	109.7
H8A—C8—H8B	107.1	H25A—C25—H25B	108.2
C8—C9—C10	107.43 (17)	O4—C26—C25	111.65 (18)
C8—C9—H9A	110.2	O4—C26—H26A	109.3
C10—C9—H9A	110.2	C25—C26—H26A	109.3
C8—C9—H9B	110.2	O4—C26—H26B	109.3
C10—C9—H9B	110.2	C25—C26—H26B	109.3
H9A—C9—H9B	108.5	H26A—C26—H26B	108.0
N2—C10—C9	114.57 (17)	O4—C27—C28	111.13 (18)
N2—C10—H10A	108.6	O4—C27—H27A	109.4
C9—C10—H10A	108.6	C28—C27—H27A	109.4
N2—C10—H10B	108.6	O4—C27—H27B	109.4
C9—C10—H10B	108.6	C28—C27—H27B	109.4
H10A—C10—H10B	107.6	H27A—C27—H27B	108.0
N2—C11—C12	109.64 (17)	N4—C28—C27	109.93 (17)
N2—C11—H11A	109.7	N4—C28—H28A	109.7
C12—C11—H11A	109.7	C27—C28—H28A	109.7
N2—C11—H11B	109.7	N4—C28—H28B	109.7
C12—C11—H11B	109.7	C27—C28—H28B	109.7
H11A—C11—H11B	108.2	H28A—C28—H28B	108.2
O2—C12—C11	112.40 (19)	H6A—O6—H6B	111 (2)
O2—C12—H12A	109.1

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O6	0.83 (2)	1.88 (2)	2.709 (2)	174 (3)
O5—H5B···N2ⁱ	0.82 (2)	2.08 (2)	2.886 (2)	170 (2)
O6—H6A···Cl1ⁱⁱ	0.84 (2)	2.34 (2)	3.1761 (16)	178 (2)
O6—H6B···N4ⁱⁱⁱ	0.86 (2)	1.99 (2)	2.834 (2)	169 (2)
C8—H8B···O6	0.99	2.56	3.551 (3)	174
C22—H22B···O5	0.99	2.51	3.154 (3)	123
C3—H3···O4^iv	0.95	2.46	3.171 (3)	132
C9—H9A···O6ⁱ	0.99	2.58	3.471 (3)	150
C27—H27B···O2^v	0.99	2.55	3.488 (3)	159
C23—H23B···Cg1^vi	0.99	2.94	3.764	141

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

Experimental details

Crystal data
Chemical formula	[Mn(C₁₄H₁₉N₂O₂)₂Cl(H₂O)]·H₂O
M_r	621.05
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.4831 (2), 12.4169 (3), 12.9518 (3)
α, β, γ (°)	95.540 (1), 90.306 (2), 104.229 (1)
V (Å³)	1470.72 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.20 × 0.16 × 0.04

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.892, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	13272, 6393, 4740
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.093, 0.99
No. of reflections	6393
No. of parameters	373
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.32

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), X-SEED (Barbour, 2001), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).