μ-Aqua-bis­(μ-4-chloro­benzoato)bis­[(4-chloro­benzoato)(1,10-phenanthroline)manganese(II)]

The title complex mol­ecule, [Mn₂(C₇H₄ClO₂)₄(C₁₂H₈N₂)₂(H₂O)], possesses crystallographically imposed C₂ symmetry. Each Mn^II atom is coordinated by three carboxyl O atoms from three 4-chloro­benzoate ligands, two N atoms from one 1,10-phenanthroline ligand and one bridging water mol­ecule in a distorted octa­hedral coordination geometry. The Mn...Mn separation is 3.512 (3) Å. Symmetrically related dinuclear mol­ecules form chains parallel to the c axis via π–π stacking inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.045
• wR factor = 0.122
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C4      ..       6.75 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C24

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

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

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

µ-Aqua-bis(µ-4-chlorobenzoato)bis[(4-chlorobenzoato)(1,10- phenanthroline)manganese(II)]

Crystal data

[Mn2(C7H4ClO2)4(C12H8N2)2(H2O)]	F(000) = 2256
Mr = 1110.51	Dx = 1.513 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2567 reflections
a = 23.4037 (4) Å	θ = 2.1–27.0°
b = 15.5866 (3) Å	µ = 0.80 mm^−1
c = 15.5960 (3) Å	T = 293 K
β = 121.012 (1)°	Block, yellow
V = 4875.96 (16) Å^3	0.30 × 0.25 × 0.18 mm
Z = 4

Data collection

Bruker APEXII area-detector diffractometer	4789 independent reflections
Radiation source: fine-focus sealed tube	3220 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
φ and ω scans	θmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −28→28
Tmin = 0.796, Tmax = 0.870	k = −18→19
16907 measured reflections	l = −18→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.049P)^2 + 3.6113P] where P = (Fo^2 + 2Fc^2)/3
4789 reflections	(Δ/σ)max = 0.001
321 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.44 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Mn1	0.95729 (2)	0.14240 (3)	0.61870 (3)	0.04110 (15)
Cl1	1.09812 (10)	0.46735 (12)	0.30516 (12)	0.1513 (7)
Cl2	1.23754 (9)	−0.29182 (9)	0.85550 (12)	0.1410 (7)
O1	1.01247 (11)	0.20592 (14)	0.56182 (17)	0.0590 (6)
O1W	1.0000	0.23392 (18)	0.7500	0.0459 (7)
H1W	1.0169	0.2680	0.7269	0.069*
O2	1.03880 (12)	0.32596 (15)	0.65308 (17)	0.0658 (6)
O3	1.02047 (10)	0.03192 (13)	0.66629 (15)	0.0522 (5)
N1	0.88572 (12)	0.06835 (16)	0.47941 (17)	0.0472 (6)
N2	0.86796 (12)	0.23075 (17)	0.52395 (18)	0.0493 (6)
C1	0.89484 (17)	−0.0113 (2)	0.4579 (2)	0.0569 (8)
H1	0.9358	−0.0375	0.4994	0.068*
C2	0.8458 (2)	−0.0575 (3)	0.3758 (3)	0.0725 (11)
H2	0.8538	−0.1131	0.3630	0.087*
C3	0.7862 (2)	−0.0189 (3)	0.3155 (3)	0.0807 (13)
H3	0.7530	−0.0485	0.2607	0.097*
C4	0.77390 (17)	0.0654 (3)	0.3347 (2)	0.0649 (10)
C5	0.71301 (19)	0.1104 (4)	0.2739 (3)	0.0842 (13)
H5	0.6782	0.0829	0.2187	0.101*
C6	0.70494 (18)	0.1905 (4)	0.2942 (3)	0.0831 (13)
H6	0.6645	0.2178	0.2528	0.100*
C7	0.75674 (16)	0.2363 (3)	0.3783 (2)	0.0637 (10)
C8	0.75078 (18)	0.3214 (3)	0.4032 (3)	0.0732 (11)
H8	0.7116	0.3519	0.3636	0.088*
C9	0.80229 (18)	0.3585 (3)	0.4850 (3)	0.0705 (10)
H9	0.7989	0.4149	0.5013	0.085*
C10	0.86019 (17)	0.3121 (2)	0.5445 (3)	0.0585 (9)
H10	0.8950	0.3384	0.6008	0.070*
C11	0.81723 (14)	0.1926 (2)	0.4411 (2)	0.0497 (8)
C12	0.82598 (15)	0.1063 (2)	0.4187 (2)	0.0501 (8)
C13	1.03232 (14)	0.2832 (2)	0.5810 (2)	0.0492 (8)
C14	1.04923 (15)	0.3275 (2)	0.5114 (2)	0.0519 (8)
C15	1.0576 (2)	0.2830 (3)	0.4425 (3)	0.0745 (11)
H15	1.0527	0.2237	0.4381	0.089*
C16	1.0735 (2)	0.3265 (3)	0.3790 (3)	0.0977 (15)
H16	1.0795	0.2963	0.3328	0.117*
C17	1.0799 (2)	0.4125 (3)	0.3853 (3)	0.0873 (13)
C18	1.0718 (2)	0.4579 (3)	0.4534 (3)	0.0842 (12)
H18	1.0760	0.5173	0.4568	0.101*
C19	1.05719 (17)	0.4147 (2)	0.5169 (3)	0.0654 (10)
H19	1.0527	0.4453	0.5642	0.079*
C20	1.07326 (14)	0.0284 (2)	0.7503 (2)	0.0445 (7)
C21	1.11302 (15)	−0.05360 (19)	0.7768 (2)	0.0460 (7)
C22	1.09239 (18)	−0.1213 (2)	0.7109 (3)	0.0574 (9)
H22	1.0527	−0.1174	0.6496	0.069*
C23	1.1304 (2)	−0.1947 (2)	0.7354 (3)	0.0768 (12)
H23	1.1163	−0.2409	0.6915	0.092*
C24	1.1897 (2)	−0.1988 (3)	0.8260 (4)	0.0839 (13)
C25	1.2111 (2)	−0.1322 (3)	0.8921 (3)	0.0850 (13)
H25	1.2512	−0.1356	0.9527	0.102*
C26	1.17241 (17)	−0.0603 (2)	0.8678 (3)	0.0644 (9)
H26	1.1861	−0.0150	0.9130	0.077*
O4	1.09546 (10)	0.08829 (13)	0.81304 (16)	0.0529 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.0380 (3)	0.0427 (3)	0.0369 (2)	0.0001 (2)	0.01527 (19)	0.00160 (19)
Cl1	0.2027 (17)	0.1730 (15)	0.1288 (12)	−0.0577 (13)	0.1214 (12)	0.0151 (11)
Cl2	0.1960 (15)	0.1122 (11)	0.1676 (14)	0.1030 (11)	0.1313 (13)	0.0775 (10)
O1	0.0685 (15)	0.0512 (15)	0.0705 (15)	−0.0041 (12)	0.0453 (13)	0.0008 (11)
O1W	0.0498 (16)	0.0467 (17)	0.0422 (15)	0.000	0.0243 (13)	0.000
O2	0.0798 (16)	0.0672 (16)	0.0596 (15)	−0.0174 (13)	0.0423 (13)	−0.0067 (12)
O3	0.0462 (12)	0.0527 (14)	0.0488 (12)	0.0076 (10)	0.0181 (10)	0.0013 (10)
N1	0.0465 (15)	0.0512 (17)	0.0388 (13)	−0.0073 (12)	0.0184 (12)	0.0019 (11)
N2	0.0420 (14)	0.0559 (17)	0.0465 (14)	0.0017 (12)	0.0204 (12)	0.0108 (12)
C1	0.063 (2)	0.056 (2)	0.0496 (18)	−0.0121 (17)	0.0272 (16)	−0.0015 (16)
C2	0.089 (3)	0.069 (3)	0.060 (2)	−0.033 (2)	0.039 (2)	−0.0176 (19)
C3	0.080 (3)	0.103 (3)	0.048 (2)	−0.049 (3)	0.025 (2)	−0.014 (2)
C4	0.056 (2)	0.085 (3)	0.0445 (18)	−0.024 (2)	0.0192 (17)	0.0022 (18)
C5	0.051 (2)	0.119 (4)	0.048 (2)	−0.026 (3)	0.0019 (18)	0.011 (2)
C6	0.040 (2)	0.126 (4)	0.058 (2)	0.000 (2)	0.0071 (18)	0.029 (3)
C7	0.0412 (18)	0.093 (3)	0.051 (2)	0.0031 (19)	0.0193 (16)	0.0251 (19)
C8	0.053 (2)	0.091 (3)	0.077 (3)	0.027 (2)	0.035 (2)	0.040 (2)
C9	0.063 (2)	0.066 (2)	0.085 (3)	0.024 (2)	0.040 (2)	0.028 (2)
C10	0.054 (2)	0.054 (2)	0.065 (2)	0.0082 (17)	0.0288 (17)	0.0103 (17)
C11	0.0376 (16)	0.065 (2)	0.0423 (17)	−0.0010 (15)	0.0180 (14)	0.0158 (15)
C12	0.0430 (18)	0.064 (2)	0.0374 (15)	−0.0121 (16)	0.0165 (14)	0.0051 (15)
C13	0.0367 (16)	0.057 (2)	0.0507 (18)	0.0031 (15)	0.0205 (14)	0.0089 (16)
C14	0.0438 (18)	0.061 (2)	0.0526 (19)	−0.0051 (15)	0.0257 (15)	0.0046 (15)
C15	0.094 (3)	0.070 (3)	0.081 (3)	−0.016 (2)	0.061 (2)	−0.007 (2)
C16	0.124 (4)	0.111 (4)	0.096 (3)	−0.030 (3)	0.084 (3)	−0.018 (3)
C17	0.103 (3)	0.097 (4)	0.076 (3)	−0.023 (3)	0.057 (3)	0.013 (2)
C18	0.102 (3)	0.074 (3)	0.087 (3)	−0.017 (2)	0.056 (3)	0.011 (2)
C19	0.071 (2)	0.062 (2)	0.066 (2)	−0.0072 (19)	0.0373 (19)	0.0039 (18)
C20	0.0398 (16)	0.0492 (19)	0.0480 (17)	−0.0013 (14)	0.0251 (15)	0.0014 (14)
C21	0.0495 (18)	0.0455 (18)	0.0476 (17)	0.0076 (14)	0.0283 (15)	0.0067 (14)
C22	0.072 (2)	0.048 (2)	0.060 (2)	0.0078 (17)	0.0387 (18)	0.0075 (16)
C23	0.119 (4)	0.048 (2)	0.092 (3)	0.012 (2)	0.075 (3)	0.007 (2)
C24	0.107 (3)	0.075 (3)	0.098 (3)	0.049 (3)	0.073 (3)	0.043 (3)
C25	0.079 (3)	0.097 (3)	0.075 (3)	0.041 (3)	0.037 (2)	0.035 (3)
C26	0.063 (2)	0.069 (2)	0.056 (2)	0.0129 (19)	0.0269 (18)	0.0080 (18)
O4	0.0471 (12)	0.0506 (13)	0.0605 (13)	−0.0037 (10)	0.0274 (11)	−0.0111 (11)

Geometric parameters (Å, º)

Mn1—O3	2.138 (2)	C8—C9	1.353 (5)
Mn1—O1	2.148 (2)	C8—H8	0.9300
Mn1—O4^i	2.173 (2)	C9—C10	1.387 (5)
Mn1—N1	2.260 (2)	C9—H9	0.9300
Mn1—O1W	2.2624 (18)	C10—H10	0.9300
Mn1—N2	2.295 (2)	C11—C12	1.431 (5)
Cl1—C17	1.739 (4)	C13—C14	1.502 (4)
Cl2—C24	1.742 (4)	C14—C19	1.369 (5)
O1—C13	1.270 (4)	C14—C15	1.375 (5)
O1W—Mn1^i	2.2623 (18)	C15—C16	1.400 (5)
O1W—H1W	0.8456	C15—H15	0.9300
O2—C13	1.247 (4)	C16—C17	1.346 (6)
O3—C20	1.256 (3)	C16—H16	0.9300
N1—C1	1.331 (4)	C17—C18	1.369 (6)
N1—C12	1.355 (4)	C18—C19	1.377 (5)
N2—C10	1.343 (4)	C18—H18	0.9300
N2—C11	1.360 (4)	C19—H19	0.9300
C1—C2	1.400 (5)	C20—O4	1.256 (3)
C1—H1	0.9300	C20—C21	1.507 (4)
C2—C3	1.356 (6)	C21—C22	1.375 (4)
C2—H2	0.9300	C21—C26	1.387 (4)
C3—C4	1.410 (6)	C22—C23	1.378 (5)
C3—H3	0.9300	C22—H22	0.9300
C4—C12	1.401 (4)	C23—C24	1.381 (6)
C4—C5	1.424 (6)	C23—H23	0.9300
C5—C6	1.326 (6)	C24—C25	1.364 (6)
C5—H5	0.9300	C25—C26	1.365 (5)
C6—C7	1.435 (5)	C25—H25	0.9300
C6—H6	0.9300	C26—H26	0.9300
C7—C8	1.409 (5)	O4—Mn1^i	2.173 (2)
C7—C11	1.413 (4)
O3—Mn1—O1	93.40 (8)	N2—C10—C9	122.6 (3)
O3—Mn1—O4^i	89.04 (8)	N2—C10—H10	118.7
O1—Mn1—O4^i	174.36 (9)	C9—C10—H10	118.7
O3—Mn1—N1	87.70 (9)	N2—C11—C7	121.4 (3)
O1—Mn1—N1	98.28 (9)	N2—C11—C12	118.5 (3)
O4^i—Mn1—N1	86.90 (8)	C7—C11—C12	120.1 (3)
O3—Mn1—O1W	106.84 (7)	N1—C12—C4	122.8 (3)
O1—Mn1—O1W	90.22 (7)	N1—C12—C11	117.8 (3)
O4^i—Mn1—O1W	84.19 (7)	C4—C12—C11	119.4 (3)
N1—Mn1—O1W	162.76 (7)	O2—C13—O1	125.4 (3)
O3—Mn1—N2	160.80 (9)	O2—C13—C14	116.8 (3)
O1—Mn1—N2	89.97 (9)	O1—C13—C14	117.8 (3)
O4^i—Mn1—N2	89.38 (8)	C19—C14—C15	118.7 (3)
N1—Mn1—N2	73.11 (9)	C19—C14—C13	119.3 (3)
O1W—Mn1—N2	92.03 (8)	C15—C14—C13	122.0 (3)
C13—O1—Mn1	124.4 (2)	C14—C15—C16	120.3 (4)
Mn1—O1W—Mn1^i	101.82 (11)	C14—C15—H15	119.8
Mn1—O1W—H1W	95.5	C16—C15—H15	119.8
Mn1^i—O1W—H1W	134.1	C17—C16—C15	119.5 (4)
C20—O3—Mn1	122.0 (2)	C17—C16—H16	120.3
C1—N1—C12	118.2 (3)	C15—C16—H16	120.3
C1—N1—Mn1	125.6 (2)	C16—C17—C18	121.0 (4)
C12—N1—Mn1	115.8 (2)	C16—C17—Cl1	119.8 (4)
C10—N2—C11	118.7 (3)	C18—C17—Cl1	119.1 (4)
C10—N2—Mn1	127.1 (2)	C17—C18—C19	119.3 (4)
C11—N2—Mn1	114.1 (2)	C17—C18—H18	120.3
N1—C1—C2	123.2 (3)	C19—C18—H18	120.3
N1—C1—H1	118.4	C14—C19—C18	121.1 (4)
C2—C1—H1	118.4	C14—C19—H19	119.4
C3—C2—C1	118.2 (4)	C18—C19—H19	119.4
C3—C2—H2	120.9	O4—C20—O3	124.7 (3)
C1—C2—H2	120.9	O4—C20—C21	117.9 (3)
C2—C3—C4	121.0 (3)	O3—C20—C21	117.4 (3)
C2—C3—H3	119.5	C22—C21—C26	119.2 (3)
C4—C3—H3	119.5	C22—C21—C20	121.0 (3)
C12—C4—C3	116.6 (3)	C26—C21—C20	119.7 (3)
C12—C4—C5	119.3 (4)	C21—C22—C23	120.1 (3)
C3—C4—C5	124.1 (4)	C21—C22—H22	119.9
C6—C5—C4	121.4 (4)	C23—C22—H22	119.9
C6—C5—H5	119.3	C22—C23—C24	119.2 (4)
C4—C5—H5	119.3	C22—C23—H23	120.4
C5—C6—C7	122.0 (4)	C24—C23—H23	120.4
C5—C6—H6	119.0	C25—C24—C23	121.5 (4)
C7—C6—H6	119.0	C25—C24—Cl2	120.0 (4)
C8—C7—C11	117.9 (3)	C23—C24—Cl2	118.6 (4)
C8—C7—C6	124.3 (4)	C24—C25—C26	118.9 (4)
C11—C7—C6	117.8 (4)	C24—C25—H25	120.6
C9—C8—C7	119.7 (3)	C26—C25—H25	120.6
C9—C8—H8	120.1	C25—C26—C21	121.1 (4)
C7—C8—H8	120.1	C25—C26—H26	119.5
C8—C9—C10	119.8 (4)	C21—C26—H26	119.5
C8—C9—H9	120.1	C20—O4—Mn1^i	124.00 (18)
C10—C9—H9	120.1

Symmetry code: (i) −x+2, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O2	0.85	1.74	2.565 (3)	167
C1—H1···O3	0.93	2.56	3.133 (3)	120
C8—H8···O4^ii	0.93	2.58	3.450 (5)	156

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