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In the title compound, [Mn(C20H16N4O2)Cl(H2O)]·C3H7NO, or [Mn(bmpb)Cl(H2O)]·DMF [H2bmpb = 1,2-bis­(4′-methyl­pyridine-2′-carboxamido)benzene and DMF is dimethyl­formamide], the MnIII ion is six-coordinate in the form of a distorted octa­hedron with two pyridine and two deprotonated amide N atoms in the equatorial plane, while the two axial sites are occupied by a chloride ion and an O atom. The structure displays O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054517/bt2573sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054517/bt2573Isup2.hkl
Contains datablock I

CCDC reference: 672687

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.059
  • wR factor = 0.178
  • Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 46 Perc. PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C7 .. 5.11 su PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N5 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C21 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C19 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C3 H7 N O
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Mn1 (3) 3.28
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 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 1 ALERT type 3 Indicator that the structure quality may be low 6 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

Manganese complexes are involved in numerous biological redox reactions performed by metalloenzymes (Larson et al., 1992). The carboxamide [–C(O)NH–] group, ubiquitous throughout nature in the primary structure of proteins, is an important ligand for coordination chemists. On the other hand, pyridine carboxamides, a burgeoning class of multidentate ligands containing this linkage, are available from condensation reactions. Here we describe the coordination chemistry of manganese(III) with a tetradentate pyridine carboxamide ligand prepared from 4-methylpyridine carboxylic acid and 1,2-diaminobenzene.

The crystal structure of the title compound is represented in Figure 1. As shown in Fig. 1, the mononuclear MnIII ion is six-coordinated, forming a distorted octahedron with two pyridine and two deprotonated amide N atoms in the equatorial plane, while the two axial sites are occupied by Cl ion and O atom provided by a water molecule. The Mn—N(amide) distances of ca 1.92 Å are significantly shorter than the Mn—N(pyridine) distances of ca 2.07 Å, both of which are appreciably shorter than the Mn—N distances found in related Mn—N4 complexes such as cis-[MnII(mep)Cl2] and [MnIII(mpp)Cl(OH2)](ClO4) [mep = N,N'-dimethyl-N,N'- bis(2-pyridylmethyl)ethane-1,2-diamino, mpp = N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)propane-1,2-diamino] (Hureau et al., 2005). The Mn—N(amide) and Mn—N(pyridine) distances are also comparable to those of [Mn(bpc)Cl(DMF)] [H2bpc =1,2- bis(2- pyridinecarboxamido)-4,5-dichlorobenzene] (Liang et al., 2007). The Mn—Cl distance at 2.463 Å is very similar to what is observed for [(mpp)MnCl(OH2)](ClO4)(Hureau et al., 2005). However, The Mn—O distance (ca 2.27 Å) in the title compound is longer than the corresponding Mn—O distances (ca 2.19 Å) in [(mpp)MnCl(OH2)](ClO4) (Hureau et al., 2005), due to the distinctive hydrogen-bond effect.

Related literature top

The complex was prepared by the reaction of Mn(CH3COO)3·2H2O and H2bmpb in DMF in the presence of LiCl (Ray et al., 1993). For other related literature, see: Larson et al. (1992); Liang et al. (2007); Hureau et al. (2005).

Experimental top

The title complex was prepared in a manner similar to the literature by the reaction of manganese(III) acetate and H2bmpb in DMF in the presence of triethylamine (Ray et al., 1993). Single crystals suitable for X-ray analysis were obtained by slow diffusion of diethyl ether into a DMF solution of the complex. Selected IR data (KBr, cm-1): 2950 (m), 1630 (amide I band, s), 1600(amide II band, s), 1480 (s), 1350 (s), 1165(s), 1020 (m), 850 (m). Analysis calculated for C23H25ClMnN5O4: C 52.53, H 4.79, Cl 6.74, N 13.32, %; found:C 52.87, H 4.32, Cl 6.78 N 12.58%. MS (FAB): 399 ([Mn(bmpb)]+).

Refinement top

All H atoms were fixed geometrically and treated as riding on their parent atoms with O—H =0.86 Å, Caromatic—H = 0.93 Å and Cmethyl—H = 0.96 Å with Uiso(H)= 1.2Ueq(C,O) or Uiso(H) = 1.5Ueq(Cmethyl).

Computing details top

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

Figures top
[Figure 1] Fig. 1. A view of anion of the title complex with displacement ellipsoids drawn at the 30% propability level. The dashed line depicts an intermolecular hydrogen bond.
Aquachlorido[4,4'-dimethyl-N,N'-(o-phenylene)bis(pyridine-2- carboxamidato)]manganese(III) dimethylformamide solvate top
Crystal data top
[Mn(C20H16N4O2)Cl(H2O)]·C3H7NOF(000) = 1088
Mr = 525.87Dx = 1.392 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.7182 (15) ÅCell parameters from 4879 reflections
b = 15.503 (2) Åθ = 1–27.5°
c = 14.0158 (19) ŵ = 0.67 mm1
β = 99.892 (3)°T = 294 K
V = 2508.4 (6) Å3Prism, black
Z = 40.24 × 0.16 × 0.12 mm
Data collection top
Bruker CCD area-detector
diffractometer
5805 independent reflections
Radiation source: fine-focus sealed tube2687 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.087
phi and ω scansθmax = 27.6°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1215
Tmin = 0.856, Tmax = 0.924k = 2017
16639 measured reflectionsl = 1817
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.075P)2]
where P = (Fo2 + 2Fc2)/3
5805 reflections(Δ/σ)max < 0.001
310 parametersΔρmax = 0.57 e Å3
0 restraintsΔρmin = 0.41 e Å3
Crystal data top
[Mn(C20H16N4O2)Cl(H2O)]·C3H7NOV = 2508.4 (6) Å3
Mr = 525.87Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.7182 (15) ŵ = 0.67 mm1
b = 15.503 (2) ÅT = 294 K
c = 14.0158 (19) Å0.24 × 0.16 × 0.12 mm
β = 99.892 (3)°
Data collection top
Bruker CCD area-detector
diffractometer
5805 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2687 reflections with I > 2σ(I)
Tmin = 0.856, Tmax = 0.924Rint = 0.087
16639 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.178H-atom parameters constrained
S = 1.02Δρmax = 0.57 e Å3
5805 reflectionsΔρmin = 0.41 e Å3
310 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
xyzUiso*/Ueq
Mn10.29430 (4)0.02350 (4)0.62328 (4)0.04348 (16)
Cl10.42626 (8)0.13481 (7)0.57974 (8)0.0620 (3)
O10.0071 (2)0.13130 (16)0.49219 (18)0.0549 (7)
O1W0.2130 (2)0.10901 (18)0.6296 (2)0.0699 (9)
H1WA0.14760.12600.59810.084*
H1WB0.22340.13600.68410.084*
O20.3918 (3)0.0425 (2)0.9130 (2)0.0834 (10)
N10.1508 (2)0.08875 (18)0.6048 (2)0.0427 (7)
N20.2379 (2)0.00161 (18)0.4774 (2)0.0452 (8)
N30.4375 (2)0.04517 (18)0.6902 (2)0.0453 (8)
N40.2958 (2)0.05783 (19)0.7554 (2)0.0463 (8)
C10.1261 (3)0.1318 (2)0.6878 (3)0.0433 (9)
C20.2085 (3)0.1156 (2)0.7712 (3)0.0463 (9)
C30.1998 (3)0.1578 (3)0.8564 (3)0.0620 (12)
H3A0.25560.14930.91130.074*
C40.1080 (4)0.2124 (3)0.8596 (3)0.0701 (13)
H4A0.10170.23990.91740.084*
C50.0266 (4)0.2269 (3)0.7800 (3)0.0668 (13)
H5A0.03460.26410.78410.080*
C60.0334 (3)0.1872 (2)0.6927 (3)0.0533 (11)
H6A0.02280.19730.63830.064*
C70.0855 (3)0.0923 (2)0.5156 (3)0.0440 (9)
C80.1376 (3)0.0425 (2)0.4426 (3)0.0435 (9)
C90.0869 (3)0.0375 (2)0.3471 (3)0.0537 (11)
H9A0.01730.06600.32590.064*
C100.1382 (4)0.0096 (3)0.2818 (3)0.0567 (11)
C110.2401 (4)0.0520 (3)0.3179 (3)0.0646 (12)
H11A0.27690.08530.27690.078*
C120.2873 (3)0.0450 (3)0.4147 (3)0.0582 (11)
H12A0.35630.07370.43760.070*
C130.3800 (3)0.0274 (3)0.8262 (3)0.0517 (10)
C140.4618 (3)0.0318 (2)0.7858 (3)0.0455 (9)
C150.5545 (3)0.0706 (2)0.8444 (3)0.0500 (10)
H15A0.56910.05960.91060.060*
C160.6255 (3)0.1261 (2)0.8037 (3)0.0507 (10)
C170.5988 (3)0.1395 (3)0.7056 (3)0.0585 (11)
H17A0.64400.17670.67570.070*
C180.5048 (3)0.0981 (3)0.6506 (3)0.0573 (11)
H18A0.48870.10770.58410.069*
C190.0836 (4)0.0150 (3)0.1775 (3)0.0816 (15)
H19A0.07640.04190.15000.122*
H19B0.00820.04070.17210.122*
H19C0.13110.04970.14320.122*
C200.7271 (3)0.1707 (3)0.8662 (3)0.0672 (13)
H20A0.78380.18590.82710.101*
H20B0.70050.22200.89390.101*
H20C0.76140.13250.91700.101*
O30.2566 (4)0.2053 (4)0.7859 (4)0.215 (3)
N50.2985 (4)0.1807 (3)0.9457 (5)0.1136 (19)
C210.3201 (5)0.2117 (4)0.8616 (5)0.113 (2)
H21A0.38990.24030.86220.135*
C220.1947 (7)0.1350 (6)0.9424 (6)0.187 (4)
H22A0.16880.11420.87780.281*
H22B0.20720.08710.98640.281*
H22C0.13700.17250.96080.281*
C230.3818 (6)0.1888 (5)1.0310 (5)0.157 (3)
H23A0.44560.22291.01770.236*
H23B0.34720.21651.08030.236*
H23C0.40900.13271.05290.236*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0350 (3)0.0512 (3)0.0443 (3)0.0053 (3)0.0072 (2)0.0028 (3)
Cl10.0529 (5)0.0601 (6)0.0785 (7)0.0063 (5)0.0268 (5)0.0082 (5)
O10.0447 (14)0.0578 (17)0.0600 (17)0.0097 (13)0.0026 (13)0.0087 (13)
O1W0.0550 (16)0.0710 (19)0.075 (2)0.0168 (14)0.0118 (14)0.0187 (16)
O20.0782 (19)0.115 (3)0.0513 (19)0.0413 (18)0.0050 (15)0.0195 (17)
N10.0363 (15)0.0497 (18)0.0422 (17)0.0003 (14)0.0071 (13)0.0009 (14)
N20.0398 (16)0.0475 (18)0.0481 (18)0.0007 (14)0.0066 (14)0.0016 (14)
N30.0397 (16)0.0483 (19)0.0474 (19)0.0026 (14)0.0060 (14)0.0056 (14)
N40.0363 (15)0.0553 (19)0.0471 (18)0.0079 (14)0.0064 (14)0.0022 (15)
C10.0381 (18)0.040 (2)0.053 (2)0.0005 (16)0.0104 (17)0.0022 (17)
C20.0423 (19)0.041 (2)0.058 (2)0.0059 (17)0.0147 (18)0.0037 (18)
C30.063 (2)0.063 (3)0.060 (3)0.011 (2)0.010 (2)0.009 (2)
C40.070 (3)0.067 (3)0.074 (3)0.018 (2)0.015 (2)0.021 (2)
C50.055 (2)0.053 (3)0.095 (3)0.014 (2)0.020 (2)0.009 (2)
C60.042 (2)0.049 (2)0.070 (3)0.0067 (18)0.0124 (19)0.003 (2)
C70.0376 (19)0.037 (2)0.058 (2)0.0066 (16)0.0102 (18)0.0058 (18)
C80.0390 (19)0.041 (2)0.050 (2)0.0031 (16)0.0071 (17)0.0077 (17)
C90.053 (2)0.055 (3)0.052 (2)0.0071 (19)0.0039 (19)0.010 (2)
C100.065 (3)0.057 (2)0.047 (2)0.019 (2)0.007 (2)0.000 (2)
C110.071 (3)0.070 (3)0.056 (3)0.009 (2)0.019 (2)0.009 (2)
C120.054 (2)0.065 (3)0.058 (3)0.007 (2)0.013 (2)0.007 (2)
C130.046 (2)0.063 (3)0.045 (2)0.007 (2)0.0024 (18)0.008 (2)
C140.0376 (18)0.046 (2)0.052 (2)0.0015 (17)0.0057 (17)0.0040 (18)
C150.045 (2)0.055 (2)0.048 (2)0.0004 (19)0.0014 (18)0.0031 (19)
C160.0375 (19)0.047 (2)0.068 (3)0.0014 (18)0.0089 (18)0.006 (2)
C170.048 (2)0.060 (3)0.070 (3)0.011 (2)0.015 (2)0.007 (2)
C180.051 (2)0.066 (3)0.055 (2)0.008 (2)0.0115 (19)0.009 (2)
C190.105 (4)0.090 (3)0.049 (3)0.020 (3)0.010 (3)0.001 (2)
C200.056 (2)0.069 (3)0.076 (3)0.013 (2)0.008 (2)0.008 (2)
O30.173 (4)0.262 (6)0.166 (4)0.105 (4)0.094 (3)0.137 (4)
N50.078 (3)0.081 (3)0.176 (6)0.003 (3)0.006 (3)0.001 (3)
C210.080 (4)0.098 (4)0.154 (6)0.018 (3)0.004 (4)0.052 (4)
C220.166 (7)0.259 (11)0.1340.005 (8)0.017 (6)0.035 (7)
C230.176 (7)0.166 (7)0.111 (6)0.031 (6)0.026 (5)0.007 (5)
Geometric parameters (Å, º) top
Mn1—N41.923 (3)C10—C111.382 (6)
Mn1—N11.941 (3)C10—C191.495 (5)
Mn1—N22.066 (3)C11—C121.380 (5)
Mn1—N32.071 (3)C11—H11A0.9300
Mn1—O1W2.273 (3)C12—H12A0.9300
Mn1—Cl12.4628 (12)C13—C141.506 (5)
O1—C71.237 (4)C14—C151.382 (5)
O1W—H1WA0.8582C15—C161.386 (5)
O1W—H1WB0.8600C15—H15A0.9300
O2—C131.223 (5)C16—C171.373 (6)
N1—C71.351 (4)C16—C201.519 (5)
N1—C11.413 (4)C17—C181.389 (5)
N2—C121.343 (5)C17—H17A0.9300
N2—C81.350 (4)C18—H18A0.9300
N3—C181.324 (5)C19—H19A0.9600
N3—C141.337 (5)C19—H19B0.9600
N4—C131.358 (4)C19—H19C0.9600
N4—C21.405 (4)C20—H20A0.9600
C1—C61.396 (5)C20—H20B0.9600
C1—C21.405 (5)C20—H20C0.9600
C2—C31.380 (5)O3—C211.190 (7)
C3—C41.376 (5)N5—C211.336 (8)
C3—H3A0.9300N5—C221.401 (9)
C4—C51.356 (6)N5—C231.413 (7)
C4—H4A0.9300C21—H21A0.9300
C5—C61.384 (6)C22—H22A0.9600
C5—H5A0.9300C22—H22B0.9600
C6—H6A0.9300C22—H22C0.9600
C7—C81.492 (5)C23—H23A0.9600
C8—C91.371 (5)C23—H23B0.9600
C9—C101.386 (6)C23—H23C0.9600
C9—H9A0.9300
N4—Mn1—N181.29 (12)C11—C10—C9117.1 (4)
N4—Mn1—N2161.16 (12)C11—C10—C19121.9 (4)
N1—Mn1—N280.28 (12)C9—C10—C19121.0 (4)
N4—Mn1—N380.40 (12)C12—C11—C10119.8 (4)
N1—Mn1—N3160.75 (12)C12—C11—H11A120.1
N2—Mn1—N3117.43 (12)C10—C11—H11A120.1
N4—Mn1—O1W98.45 (12)N2—C12—C11122.8 (4)
N1—Mn1—O1W96.71 (11)N2—C12—H12A118.6
N2—Mn1—O1W79.93 (11)C11—C12—H12A118.6
N3—Mn1—O1W80.21 (10)O2—C13—N4127.2 (4)
N4—Mn1—Cl198.18 (9)O2—C13—C14121.3 (3)
N1—Mn1—Cl199.69 (9)N4—C13—C14111.5 (3)
N2—Mn1—Cl188.73 (9)N3—C14—C15122.5 (3)
N3—Mn1—Cl188.75 (9)N3—C14—C13115.6 (3)
O1W—Mn1—Cl1158.17 (9)C15—C14—C13121.9 (3)
Mn1—O1W—H1WA126.9C14—C15—C16119.5 (4)
Mn1—O1W—H1WB118.6C14—C15—H15A120.3
H1WA—O1W—H1WB106.6C16—C15—H15A120.3
C7—N1—C1125.5 (3)C17—C16—C15117.2 (3)
C7—N1—Mn1118.9 (2)C17—C16—C20122.0 (4)
C1—N1—Mn1115.6 (2)C15—C16—C20120.8 (4)
C12—N2—C8117.6 (3)C16—C17—C18120.5 (4)
C12—N2—Mn1129.4 (3)C16—C17—H17A119.7
C8—N2—Mn1113.0 (2)C18—C17—H17A119.7
C18—N3—C14118.5 (3)N3—C18—C17121.8 (4)
C18—N3—Mn1128.5 (3)N3—C18—H18A119.1
C14—N3—Mn1113.0 (2)C17—C18—H18A119.1
C13—N4—C2124.3 (3)C10—C19—H19A109.5
C13—N4—Mn1119.5 (2)C10—C19—H19B109.5
C2—N4—Mn1116.2 (2)H19A—C19—H19B109.5
C6—C1—C2119.9 (3)C10—C19—H19C109.5
C6—C1—N1127.0 (3)H19A—C19—H19C109.5
C2—C1—N1113.0 (3)H19B—C19—H19C109.5
C3—C2—C1119.5 (3)C16—C20—H20A109.5
C3—C2—N4127.0 (3)C16—C20—H20B109.5
C1—C2—N4113.5 (3)H20A—C20—H20B109.5
C4—C3—C2119.6 (4)C16—C20—H20C109.5
C4—C3—H3A120.2H20A—C20—H20C109.5
C2—C3—H3A120.2H20B—C20—H20C109.5
C5—C4—C3121.2 (4)C21—N5—C22116.6 (6)
C5—C4—H4A119.4C21—N5—C23120.4 (6)
C3—C4—H4A119.4C22—N5—C23122.8 (7)
C4—C5—C6120.9 (4)O3—C21—N5124.9 (7)
C4—C5—H5A119.5O3—C21—H21A117.5
C6—C5—H5A119.5N5—C21—H21A117.5
C5—C6—C1118.7 (4)N5—C22—H22A109.5
C5—C6—H6A120.6N5—C22—H22B109.5
C1—C6—H6A120.6H22A—C22—H22B109.5
O1—C7—N1126.6 (3)N5—C22—H22C109.5
O1—C7—C8121.0 (3)H22A—C22—H22C109.5
N1—C7—C8112.4 (3)H22B—C22—H22C109.5
N2—C8—C9122.0 (3)N5—C23—H23A109.5
N2—C8—C7115.3 (3)N5—C23—H23B109.5
C9—C8—C7122.6 (3)H23A—C23—H23B109.5
C8—C9—C10120.7 (4)N5—C23—H23C109.5
C8—C9—H9A119.7H23A—C23—H23C109.5
C10—C9—H9A119.7H23B—C23—H23C109.5
N4—Mn1—N1—C7177.1 (3)C1—C2—C3—C42.6 (6)
N2—Mn1—N1—C71.0 (2)N4—C2—C3—C4179.9 (4)
N3—Mn1—N1—C7159.0 (3)C2—C3—C4—C51.2 (7)
O1W—Mn1—N1—C779.5 (3)C3—C4—C5—C60.1 (7)
Cl1—Mn1—N1—C786.0 (2)C4—C5—C6—C10.2 (6)
N4—Mn1—N1—C15.2 (2)C2—C1—C6—C51.6 (5)
N2—Mn1—N1—C1178.7 (3)N1—C1—C6—C5176.8 (4)
N3—Mn1—N1—C123.3 (5)C1—N1—C7—O12.1 (6)
O1W—Mn1—N1—C1102.7 (2)Mn1—N1—C7—O1179.6 (3)
Cl1—Mn1—N1—C191.7 (2)C1—N1—C7—C8177.7 (3)
N4—Mn1—N2—C12167.7 (4)Mn1—N1—C7—C80.2 (4)
N1—Mn1—N2—C12179.7 (3)C12—N2—C8—C90.0 (5)
N3—Mn1—N2—C127.7 (4)Mn1—N2—C8—C9178.8 (3)
O1W—Mn1—N2—C1281.0 (3)C12—N2—C8—C7179.2 (3)
Cl1—Mn1—N2—C1280.2 (3)Mn1—N2—C8—C72.0 (4)
N4—Mn1—N2—C813.6 (5)O1—C7—C8—N2179.0 (3)
N1—Mn1—N2—C81.6 (2)N1—C7—C8—N21.2 (4)
N3—Mn1—N2—C8173.7 (2)O1—C7—C8—C90.2 (5)
O1W—Mn1—N2—C8100.3 (2)N1—C7—C8—C9179.5 (3)
Cl1—Mn1—N2—C898.4 (2)N2—C8—C9—C100.8 (5)
N4—Mn1—N3—C18178.9 (3)C7—C8—C9—C10179.9 (3)
N1—Mn1—N3—C18160.8 (3)C8—C9—C10—C111.4 (6)
N2—Mn1—N3—C185.3 (4)C8—C9—C10—C19179.7 (4)
O1W—Mn1—N3—C1878.5 (3)C9—C10—C11—C121.2 (6)
Cl1—Mn1—N3—C1882.6 (3)C19—C10—C11—C12179.9 (4)
N4—Mn1—N3—C141.4 (2)C8—N2—C12—C110.2 (6)
N1—Mn1—N3—C1419.6 (5)Mn1—N2—C12—C11178.4 (3)
N2—Mn1—N3—C14175.0 (2)C10—C11—C12—N20.4 (6)
O1W—Mn1—N3—C14101.8 (3)C2—N4—C13—O22.3 (7)
Cl1—Mn1—N3—C1497.1 (2)Mn1—N4—C13—O2179.1 (4)
N1—Mn1—N4—C13175.0 (3)C2—N4—C13—C14178.9 (3)
N2—Mn1—N4—C13163.0 (3)Mn1—N4—C13—C140.3 (4)
N3—Mn1—N4—C130.9 (3)C18—N3—C14—C150.4 (5)
O1W—Mn1—N4—C1379.4 (3)Mn1—N3—C14—C15179.3 (3)
Cl1—Mn1—N4—C1386.4 (3)C18—N3—C14—C13178.6 (3)
N1—Mn1—N4—C26.4 (2)Mn1—N3—C14—C131.7 (4)
N2—Mn1—N4—C218.3 (5)O2—C13—C14—N3177.9 (4)
N3—Mn1—N4—C2179.6 (3)N4—C13—C14—N31.0 (5)
O1W—Mn1—N4—C2101.9 (3)O2—C13—C14—C151.0 (6)
Cl1—Mn1—N4—C292.3 (2)N4—C13—C14—C15180.0 (3)
C7—N1—C1—C62.1 (6)N3—C14—C15—C160.4 (6)
Mn1—N1—C1—C6175.4 (3)C13—C14—C15—C16178.6 (3)
C7—N1—C1—C2179.3 (3)C14—C15—C16—C170.1 (5)
Mn1—N1—C1—C23.1 (4)C14—C15—C16—C20179.2 (3)
C6—C1—C2—C32.9 (5)C15—C16—C17—C180.6 (6)
N1—C1—C2—C3175.8 (3)C20—C16—C17—C18179.6 (4)
C6—C1—C2—N4179.3 (3)C14—N3—C18—C170.1 (6)
N1—C1—C2—N42.0 (4)Mn1—N3—C18—C17179.8 (3)
C13—N4—C2—C37.4 (6)C16—C17—C18—N30.6 (6)
Mn1—N4—C2—C3171.2 (3)C22—N5—C21—O32.2 (10)
C13—N4—C2—C1175.0 (3)C23—N5—C21—O3177.5 (6)
Mn1—N4—C2—C16.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O1i0.861.902.728 (3)162.3
O1W—H1WB···O30.861.782.627 (5)170.2
Symmetry code: (i) x, y, z+1.

Experimental details

Crystal data
Chemical formula[Mn(C20H16N4O2)Cl(H2O)]·C3H7NO
Mr525.87
Crystal system, space groupMonoclinic, P21/c
Temperature (K)294
a, b, c (Å)11.7182 (15), 15.503 (2), 14.0158 (19)
β (°) 99.892 (3)
V3)2508.4 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.67
Crystal size (mm)0.24 × 0.16 × 0.12
Data collection
DiffractometerBruker CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.856, 0.924
No. of measured, independent and
observed [I > 2σ(I)] reflections
16639, 5805, 2687
Rint0.087
(sin θ/λ)max1)0.652
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.178, 1.02
No. of reflections5805
No. of parameters310
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.57, 0.41

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O1i0.861.902.728 (3)162.3
O1W—H1WB···O30.861.782.627 (5)170.2
Symmetry code: (i) x, y, z+1.
 

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