cis-Dichloridobis(1,10-phenanthroline-κN,N')manganese(II)-2,6-dihydroxy-benzoic acid-water (2/1/4).

In the crystal structure of the title compound, [MnCl(2)(C(12)H(8)N(2))(2)]·0.5C(7)H(6)O(4)·2H(2)O, the Mn(II) complex assumes a distorted octa-hedral geometry formed by two chloride anions and two phenanthroline (phen) ligands. The 2,6-dihydroxy-benzoic acid mol-ecule is disordered about an inversion center. The face-to-face separations of 3.540 (11) and 3.429 (8) Å between parallel phen ligands indicate the existence of π-π stacking between adjacent Mn(II) complexes. Uncoordinated water mol-ecules are linked with complex and dihydroxy-benzoic acid mol-ecules via O-H⋯Cl and O-H⋯O hydrogen bonds.

Related literature

For general background, see: Su & Xu (2004 ▶). For related structures, see: McCann et al. (1998 ▶); Pan & Xu (2005 ▶).

Experimental

Crystal data

[MnCl2(C12H8N2)2]·0.5C7H6O4·2H2O

M = 599.34

Triclinic,

a = 9.757 (2) Å

b = 11.985 (3) Å

c = 13.261 (3) Å

α = 63.465 (17)°

β = 83.931 (18)°

γ = 76.819 (18)°

V = 1350.8 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.73 mm−1

T = 295 (2) K

0.42 × 0.36 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.735, T max = 0.860

14401 measured reflections

4680 independent reflections

3662 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.191

S = 1.08

4680 reflections

355 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −1.16 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808012427/ng2452sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012427/ng2452Isup2.hkl

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

[MnCl2(C12H8N2)2]·0.5C7H6O4·2H2O	Z = 2
Mr = 599.34	F000 = 614
Triclinic, P1	Dx = 1.474 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.757 (2) Å	Cell parameters from 6825 reflections
b = 11.985 (3) Å	θ = 1.8–25.0º
c = 13.261 (3) Å	µ = 0.73 mm−1
α = 63.465 (17)º	T = 295 (2) K
β = 83.931 (18)º	Prism, yellow
γ = 76.819 (18)º	0.42 × 0.36 × 0.20 mm
V = 1350.8 (6) Å3

Rigaku R-AXIS RAPID IP diffractometer	4680 independent reflections
Radiation source: fine-focus sealed tube	3662 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.029
Detector resolution: 10.00 pixels mm-1	θmax = 25.0º
T = 295(2) K	θmin = 1.7º
ω scans	h = −10→11
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	k = −12→13
Tmin = 0.735, Tmax = 0.860	l = −15→15
14401 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059	H-atom parameters constrained
wR(F2) = 0.191	w = 1/[σ2(Fo2) + (0.115P)2 + 0.6925P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
4680 reflections	Δρmax = 0.55 e Å−3
355 parameters	Δρmin = −1.16 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	Occ. (<1)
Mn	0.81692 (6)	0.12805 (5)	0.21903 (4)	0.0452 (2)
Cl1	0.9994 (2)	0.09801 (17)	0.08753 (14)	0.1086 (6)
Cl2	0.93733 (10)	−0.05166 (9)	0.38297 (8)	0.0543 (3)
N1	0.8875 (3)	0.2844 (3)	0.2384 (3)	0.0512 (8)
N2	0.7264 (4)	0.3198 (3)	0.0676 (3)	0.0558 (8)
N3	0.6117 (3)	0.1579 (3)	0.3159 (2)	0.0467 (7)
N4	0.6685 (3)	0.0238 (3)	0.1901 (3)	0.0531 (8)
O1	0.4543 (14)	0.3988 (12)	0.7173 (9)	0.132 (4)	0.50
H1C	0.3709	0.3781	0.7149	0.197*	0.50
O2	0.4410 (16)	0.5884 (14)	0.3174 (9)	0.146 (4)	0.50
H2C	0.3551	0.5690	0.3274	0.220*	0.50
O3	0.2390 (11)	0.4282 (12)	0.6173 (11)	0.135 (4)	0.50
O4	0.2332 (11)	0.5254 (11)	0.4305 (10)	0.127 (3)	0.50
H4A	0.1410	0.5328	0.4354	0.191*	0.50
O1W	0.0193 (5)	0.2911 (4)	0.6726 (4)	0.1147 (15)
H1A	0.0606	0.3531	0.6449	0.172*
H1B	−0.0422	0.3081	0.7116	0.172*
O2W	0.8797 (5)	0.1644 (5)	−0.1317 (3)	0.1292 (19)
H2A	0.9009	0.0907	−0.1291	0.194*
H2B	0.9163	0.1605	−0.0767	0.194*
C1	0.9627 (5)	0.2673 (5)	0.3244 (4)	0.0654 (12)
H1	0.9819	0.1864	0.3842	0.078*
C2	1.0141 (6)	0.3642 (6)	0.3295 (6)	0.0855 (16)
H2	1.0653	0.3483	0.3915	0.103*
C3	0.9875 (6)	0.4838 (6)	0.2409 (6)	0.0879 (17)
H3	1.0224	0.5495	0.2416	0.105*
C4	0.9086 (5)	0.5059 (4)	0.1508 (5)	0.0719 (13)
C5	0.8757 (7)	0.6265 (5)	0.0563 (6)	0.099 (2)
H5	0.9101	0.6943	0.0530	0.119*
C6	0.7955 (8)	0.6450 (5)	−0.0291 (6)	0.101 (2)
H6	0.7754	0.7256	−0.0891	0.121*
C7	0.7401 (5)	0.5436 (5)	−0.0299 (4)	0.0750 (15)
C8	0.6572 (7)	0.5591 (6)	−0.1146 (4)	0.096 (2)
H8	0.6344	0.6384	−0.1758	0.115*
C9	0.6079 (6)	0.4583 (7)	−0.1093 (4)	0.095 (2)
H9	0.5503	0.4694	−0.1661	0.115*
C10	0.6453 (5)	0.3365 (5)	−0.0163 (4)	0.0746 (14)
H10	0.6135	0.2676	−0.0135	0.089*
C11	0.7730 (4)	0.4222 (4)	0.0615 (3)	0.0560 (10)
C12	0.8574 (4)	0.4022 (4)	0.1523 (3)	0.0529 (9)
C13	0.5854 (4)	0.2205 (4)	0.3785 (3)	0.0559 (10)
H13	0.6523	0.2638	0.3805	0.067*
C14	0.4616 (5)	0.2253 (4)	0.4424 (4)	0.0623 (11)
H14	0.4472	0.2706	0.4855	0.075*
C15	0.3644 (5)	0.1629 (4)	0.4398 (3)	0.0615 (11)
H15	0.2821	0.1644	0.4820	0.074*
C16	0.3863 (4)	0.0947 (4)	0.3733 (3)	0.0530 (10)
C17	0.2874 (4)	0.0270 (4)	0.3665 (4)	0.0643 (12)
H17	0.2036	0.0266	0.4071	0.077*
C18	0.3139 (5)	−0.0362 (5)	0.3023 (4)	0.0709 (13)
H18	0.2469	−0.0780	0.2980	0.085*
C19	0.4431 (4)	−0.0408 (4)	0.2403 (4)	0.0608 (11)
C20	0.4783 (5)	−0.1079 (5)	0.1742 (4)	0.0751 (13)
H20	0.4143	−0.1507	0.1669	0.090*
C21	0.6039 (6)	−0.1109 (6)	0.1212 (5)	0.0800 (15)
H21	0.6277	−0.1575	0.0794	0.096*
C22	0.6973 (5)	−0.0441 (5)	0.1296 (4)	0.0664 (12)
H22	0.7833	−0.0462	0.0921	0.080*
C23	0.5434 (4)	0.0246 (4)	0.2452 (3)	0.0491 (9)
C24	0.5137 (4)	0.0953 (3)	0.3123 (3)	0.0453 (8)
C30	0.2957 (16)	0.4791 (16)	0.5273 (14)	0.098 (4)	0.50
C31	0.4417 (8)	0.4897 (11)	0.5167 (7)	0.0936 (16)	0.50
C32	0.5181 (10)	0.4401 (9)	0.6154 (6)	0.0936 (16)	0.50
C33	0.6607 (9)	0.4420 (9)	0.6100 (7)	0.0936 (16)	0.50
H33	0.7119	0.4088	0.6761	0.112*	0.50
C34	0.7267 (8)	0.4935 (10)	0.5060 (9)	0.0936 (16)	0.50
H34	0.8221	0.4948	0.5024	0.112*	0.50
C35	0.6503 (10)	0.5431 (9)	0.4073 (7)	0.0936 (16)	0.50
H35	0.6945	0.5775	0.3377	0.112*	0.50
C36	0.5077 (10)	0.5412 (9)	0.4127 (6)	0.0936 (16)	0.50

	U11	U22	U33	U12	U13	U23
Mn	0.0442 (4)	0.0484 (4)	0.0457 (3)	−0.0130 (3)	0.0024 (2)	−0.0218 (3)
Cl1	0.1378 (15)	0.1000 (12)	0.0928 (10)	−0.0370 (10)	0.0080 (9)	−0.0421 (9)
Cl2	0.0508 (6)	0.0569 (6)	0.0510 (5)	−0.0092 (4)	−0.0020 (4)	−0.0203 (4)
N1	0.0456 (18)	0.0515 (19)	0.0585 (19)	−0.0100 (14)	0.0004 (14)	−0.0260 (16)
N2	0.0507 (19)	0.061 (2)	0.0484 (17)	−0.0017 (16)	−0.0026 (14)	−0.0216 (16)
N3	0.0403 (17)	0.0464 (17)	0.0496 (16)	−0.0062 (13)	0.0019 (13)	−0.0194 (14)
N4	0.0447 (18)	0.065 (2)	0.0572 (18)	−0.0139 (15)	0.0030 (14)	−0.0323 (17)
O1	0.140 (10)	0.152 (9)	0.093 (7)	−0.070 (8)	0.013 (6)	−0.030 (6)
O2	0.171 (12)	0.210 (13)	0.086 (7)	−0.077 (10)	0.002 (7)	−0.071 (8)
O3	0.103 (7)	0.172 (10)	0.165 (10)	−0.063 (7)	0.031 (7)	−0.095 (9)
O4	0.095 (7)	0.158 (9)	0.146 (9)	−0.001 (6)	−0.006 (7)	−0.091 (8)
O1W	0.141 (4)	0.098 (3)	0.126 (4)	−0.037 (3)	0.024 (3)	−0.068 (3)
O2W	0.099 (3)	0.146 (4)	0.077 (2)	0.022 (3)	0.002 (2)	−0.014 (3)
C1	0.062 (3)	0.068 (3)	0.078 (3)	−0.010 (2)	−0.013 (2)	−0.041 (2)
C2	0.070 (3)	0.097 (4)	0.122 (5)	−0.007 (3)	−0.015 (3)	−0.078 (4)
C3	0.067 (3)	0.089 (4)	0.144 (5)	−0.026 (3)	0.008 (3)	−0.079 (4)
C4	0.064 (3)	0.049 (3)	0.105 (4)	−0.015 (2)	0.026 (3)	−0.040 (3)
C5	0.099 (5)	0.055 (3)	0.127 (5)	−0.027 (3)	0.038 (4)	−0.028 (3)
C6	0.112 (5)	0.047 (3)	0.101 (4)	−0.009 (3)	0.040 (4)	−0.008 (3)
C7	0.070 (3)	0.059 (3)	0.061 (3)	0.005 (2)	0.018 (2)	−0.007 (2)
C8	0.098 (4)	0.085 (4)	0.057 (3)	0.019 (3)	0.004 (3)	−0.009 (3)
C9	0.083 (4)	0.128 (5)	0.050 (3)	0.025 (4)	−0.018 (2)	−0.035 (3)
C10	0.071 (3)	0.093 (4)	0.052 (2)	0.005 (3)	−0.011 (2)	−0.032 (2)
C11	0.053 (2)	0.049 (2)	0.052 (2)	−0.0009 (18)	0.0151 (18)	−0.0174 (18)
C12	0.045 (2)	0.047 (2)	0.064 (2)	−0.0090 (17)	0.0112 (18)	−0.0249 (19)
C13	0.055 (2)	0.056 (2)	0.058 (2)	−0.0078 (19)	0.0042 (18)	−0.028 (2)
C14	0.066 (3)	0.059 (3)	0.058 (2)	−0.001 (2)	0.007 (2)	−0.028 (2)
C15	0.049 (2)	0.060 (3)	0.056 (2)	0.003 (2)	0.0095 (18)	−0.017 (2)
C16	0.039 (2)	0.056 (2)	0.047 (2)	−0.0011 (17)	−0.0008 (16)	−0.0113 (18)
C17	0.042 (2)	0.073 (3)	0.067 (3)	−0.013 (2)	0.0020 (19)	−0.021 (2)
C18	0.047 (2)	0.089 (3)	0.074 (3)	−0.025 (2)	−0.005 (2)	−0.027 (3)
C19	0.051 (2)	0.070 (3)	0.063 (2)	−0.019 (2)	−0.0091 (19)	−0.026 (2)
C20	0.066 (3)	0.093 (4)	0.088 (3)	−0.033 (3)	−0.004 (2)	−0.050 (3)
C21	0.079 (3)	0.103 (4)	0.091 (3)	−0.030 (3)	0.003 (3)	−0.066 (3)
C22	0.065 (3)	0.086 (3)	0.071 (3)	−0.025 (2)	0.009 (2)	−0.052 (3)
C23	0.043 (2)	0.055 (2)	0.0457 (19)	−0.0085 (16)	−0.0057 (15)	−0.0180 (17)
C24	0.0361 (19)	0.049 (2)	0.0396 (17)	−0.0025 (15)	−0.0032 (14)	−0.0116 (16)
C30	0.076 (8)	0.114 (11)	0.116 (12)	−0.018 (8)	0.007 (8)	−0.062 (10)
C31	0.097 (4)	0.090 (3)	0.101 (4)	−0.021 (3)	0.013 (3)	−0.050 (4)
C32	0.097 (4)	0.090 (3)	0.101 (4)	−0.021 (3)	0.013 (3)	−0.050 (4)
C33	0.097 (4)	0.090 (3)	0.101 (4)	−0.021 (3)	0.013 (3)	−0.050 (4)
C34	0.097 (4)	0.090 (3)	0.101 (4)	−0.021 (3)	0.013 (3)	−0.050 (4)
C35	0.097 (4)	0.090 (3)	0.101 (4)	−0.021 (3)	0.013 (3)	−0.050 (4)
C36	0.097 (4)	0.090 (3)	0.101 (4)	−0.021 (3)	0.013 (3)	−0.050 (4)

Mn—N1	2.260 (3)	C7—C11	1.408 (6)
Mn—N2	2.328 (3)	C8—C9	1.370 (9)
Mn—N3	2.308 (3)	C8—H8	0.9300
Mn—N4	2.275 (3)	C9—C10	1.425 (8)
Mn—Cl1	2.440 (2)	C9—H9	0.9300
Mn—Cl2	2.4387 (13)	C10—H10	0.9300
N1—C1	1.334 (5)	C11—C12	1.430 (6)
N1—C12	1.351 (5)	C13—C14	1.405 (6)
N2—C10	1.350 (6)	C13—H13	0.9300
N2—C11	1.370 (6)	C14—C15	1.348 (7)
N3—C13	1.319 (5)	C14—H14	0.9300
N3—C24	1.360 (5)	C15—C16	1.419 (6)
N4—C22	1.347 (5)	C15—H15	0.9300
N4—C23	1.355 (5)	C16—C24	1.410 (5)
O1—C32	1.351 (12)	C16—C17	1.428 (6)
O1—H1C	0.9109	C17—C18	1.344 (7)
O2—C36	1.307 (13)	C17—H17	0.9300
O2—H2C	0.9016	C18—C19	1.434 (7)
O3—C30	1.211 (17)	C18—H18	0.9300
O4—C30	1.305 (17)	C19—C20	1.405 (7)
O4—H4A	0.8817	C19—C23	1.409 (6)
O1W—H1A	0.8434	C20—C21	1.348 (7)
O1W—H1B	0.8012	C20—H20	0.9300
O2W—H2A	0.8461	C21—C22	1.385 (7)
O2W—H2B	0.8246	C21—H21	0.9300
C1—C2	1.396 (7)	C22—H22	0.9300
C1—H1	0.9300	C23—C24	1.449 (5)
C2—C3	1.376 (8)	C30—C31	1.445 (15)
C2—H2	0.9300	C31—C32	1.3900
C3—C4	1.381 (8)	C31—C36	1.3900
C3—H3	0.9300	C32—C33	1.3900
C4—C5	1.421 (8)	C33—C34	1.3900
C4—C12	1.432 (6)	C33—H33	0.9300
C5—C6	1.351 (10)	C34—C35	1.3900
C5—H5	0.9300	C34—H34	0.9300
C6—C7	1.443 (9)	C35—C36	1.3900
C6—H6	0.9300	C35—H35	0.9300
C7—C8	1.373 (8)
N1—Mn—N4	158.51 (12)	N2—C11—C12	117.6 (3)
N1—Mn—N3	90.22 (12)	C7—C11—C12	120.3 (5)
N4—Mn—N3	73.23 (12)	N1—C12—C11	118.7 (4)
N1—Mn—N2	72.54 (12)	N1—C12—C4	121.2 (4)
N4—Mn—N2	92.82 (13)	C11—C12—C4	120.1 (4)
N3—Mn—N2	87.93 (11)	N3—C13—C14	123.4 (4)
N1—Mn—Cl2	97.72 (9)	N3—C13—H13	118.3
N4—Mn—Cl2	97.17 (9)	C14—C13—H13	118.3
N3—Mn—Cl2	94.48 (8)	C15—C14—C13	118.5 (4)
N2—Mn—Cl2	170.00 (10)	C15—C14—H14	120.7
N1—Mn—Cl1	98.05 (9)	C13—C14—H14	120.7
N4—Mn—Cl1	96.38 (9)	C14—C15—C16	120.6 (4)
N3—Mn—Cl1	167.55 (9)	C14—C15—H15	119.7
N2—Mn—Cl1	85.73 (9)	C16—C15—H15	119.7
Cl2—Mn—Cl1	93.61 (6)	C24—C16—C15	116.8 (4)
C1—N1—C12	118.4 (4)	C24—C16—C17	119.8 (4)
C1—N1—Mn	125.0 (3)	C15—C16—C17	123.4 (4)
C12—N1—Mn	116.5 (3)	C18—C17—C16	120.9 (4)
C10—N2—C11	118.8 (4)	C18—C17—H17	119.6
C10—N2—Mn	126.9 (3)	C16—C17—H17	119.6
C11—N2—Mn	114.0 (3)	C17—C18—C19	121.6 (4)
C13—N3—C24	118.4 (3)	C17—C18—H18	119.2
C13—N3—Mn	127.1 (3)	C19—C18—H18	119.2
C24—N3—Mn	114.3 (2)	C20—C19—C23	116.7 (4)
C22—N4—C23	117.9 (4)	C20—C19—C18	124.2 (4)
C22—N4—Mn	126.1 (3)	C23—C19—C18	119.1 (4)
C23—N4—Mn	115.9 (3)	C21—C20—C19	120.6 (4)
C32—O1—H1C	111.8	C21—C20—H20	119.7
C36—O2—H2C	111.9	C19—C20—H20	119.7
C30—O4—H4A	114.1	C20—C21—C22	119.5 (5)
H1A—O1W—H1B	105.4	C20—C21—H21	120.2
H2A—O2W—H2B	107.1	C22—C21—H21	120.2
N1—C1—C2	123.5 (5)	N4—C22—C21	122.5 (4)
N1—C1—H1	118.2	N4—C22—H22	118.7
C2—C1—H1	118.2	C21—C22—H22	118.7
C3—C2—C1	118.6 (5)	N4—C23—C19	122.7 (4)
C3—C2—H2	120.7	N4—C23—C24	117.9 (3)
C1—C2—H2	120.7	C19—C23—C24	119.4 (4)
C2—C3—C4	119.7 (5)	N3—C24—C16	122.3 (4)
C2—C3—H3	120.2	N3—C24—C23	118.6 (3)
C4—C3—H3	120.2	C16—C24—C23	119.2 (4)
C3—C4—C5	123.3 (5)	O3—C30—O4	123.6 (16)
C3—C4—C12	118.6 (5)	O3—C30—C31	123.0 (14)
C5—C4—C12	118.1 (6)	O4—C30—C31	113.3 (14)
C6—C5—C4	121.5 (6)	C32—C31—C36	120.0
C6—C5—H5	119.3	C32—C31—C30	117.6 (8)
C4—C5—H5	119.3	C36—C31—C30	122.4 (8)
C5—C6—C7	122.1 (5)	O1—C32—C31	121.1 (8)
C5—C6—H6	119.0	O1—C32—C33	118.7 (8)
C7—C6—H6	119.0	C31—C32—C33	120.0
C8—C7—C11	118.4 (6)	C32—C33—C34	120.0
C8—C7—C6	123.7 (5)	C32—C33—H33	120.0
C11—C7—C6	117.9 (5)	C34—C33—H33	120.0
C9—C8—C7	120.4 (5)	C35—C34—C33	120.0
C9—C8—H8	119.8	C35—C34—H34	120.0
C7—C8—H8	119.8	C33—C34—H34	120.0
C8—C9—C10	119.5 (5)	C36—C35—C34	120.0
C8—C9—H9	120.2	C36—C35—H35	120.0
C10—C9—H9	120.2	C34—C35—H35	120.0
N2—C10—C9	120.8 (6)	O2—C36—C35	117.5 (9)
N2—C10—H10	119.6	O2—C36—C31	122.5 (9)
C9—C10—H10	119.6	C35—C36—C31	120.0
N2—C11—C7	122.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O3	0.84	2.06	2.834 (13)	152
O1W—H1B···O2Wi	0.80	2.22	2.752 (6)	124
O2W—H2A···Cl1ii	0.85	2.09	2.904 (6)	162
O2W—H2B···Cl1	0.82	2.14	2.946 (4)	164
O1—H1C···O3	0.91	1.73	2.476 (18)	137
O2—H2C···O4	0.90	1.69	2.444 (19)	139
O4—H4A···O1Wiii	0.88	2.28	2.886 (13)	125
C3—H3···O1Wiv	0.93	2.57	3.356 (9)	143
C5—H5···Cl1v	0.93	2.64	3.427 (7)	143
C9—H9···O1vi	0.93	2.41	3.275 (15)	154
C9—H9···O2vii	0.93	2.39	3.152 (15)	140
C15—H15···Cl2viii	0.93	2.82	3.674 (5)	153

Table 1

Selected bond lengths (Å)

Mn—N1	2.260 (3)
Mn—N2	2.328 (3)
Mn—N3	2.308 (3)
Mn—N4	2.275 (3)
Mn—Cl1	2.440 (2)
Mn—Cl2	2.4387 (13)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯O3	0.84	2.06	2.834 (13)	152
O1W—H1B⋯O2Wi	0.80	2.22	2.752 (6)	124
O2W—H2A⋯Cl1ii	0.85	2.09	2.904 (6)	162
O2W—H2B⋯Cl1	0.82	2.14	2.946 (4)	164
O1—H1C⋯O3	0.91	1.73	2.476 (18)	137
O2—H2C⋯O4	0.90	1.69	2.444 (19)	139
O4—H4A⋯O1Wiii	0.88	2.28	2.886 (13)	125

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