Bis[6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinato]manganese(II) trihydrate

Feng, Y.; Kai, Z.; Yin, X.-H.; Zhu, J.; Lin, C.-W.

doi:10.1107/S160053680706388X

Bis[6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinato]manganese(II) trihydrate

Y. Feng, Z. Kai, X.-H. Yin, J. Zhu and C.-W. Lin

In the title complex, [Mn(C₁₁H₁₀N₃O₂)₂]·3H₂O, the Mn^II atom is coordinated by four N atoms and two O atoms in a distorted octahedral geometry. The molecules are linked together via hydrogen bonds involving the water molecules. One of these is disordered equally over two positions.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680706388X/sg2211sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680706388X/sg2211Isup2.hkl Contains datablock I

CCDC reference: 665032

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
Disorder in solvent or counterion
R factor = 0.048
wR factor = 0.150
Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H6B    ..  H7D     ..       2.00 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H6B    ..  H7E     ..       2.06 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.99
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.30
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O3
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      25.00 Perc.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          3
            N4  -MN1 -N1  -C6     56.00  2.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          8
            N4  -MN1 -N1  -C2   -116.00  2.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         27
            N1  -MN1 -N4  -C17  -153.00  2.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         32
            N1  -MN1 -N4  -C13    31.00  2.00   1.555   1.555   1.555   1.555

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
   2 ALERT level B = Potentially serious problem
  12 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   7 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Recently we reported the crystal structures of bis(6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinato)zinc(II) trihydrate (Yin et al., 2007) and bis[3-chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinato]cobalt(II) 2.5- hydrate (Zhao et al., 2007). As a continuation of these investigations, we report in this paper the crystal structure of Bis(6-(3,5-dimethyl-1H-pyrazol-1-yl) picolinato)manganese(II)trihydrate.

The structure consists of the manganese(II) complex and three uncoordinated water molecules. The Mn atom is six-coordinated by four N atoms and two O atoms derived from the tridentate ligands, 6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinate (DPP), that define a distorted octahedral environment; the Mn—O bond lengths are 2.143 (3) and 2.154 (3) Å, The Mn—N distances range from 2.199 (3) to 2.277 (3) Å, i.e. normal values, The C1—C2 bond length is 1.522 (5) Å, being in the normal C—C ranges in manganese carboxylate complexes.

In the crystal structure, the oxygen atoms contribute to the formation of intermolecular hydrogen bonds involving the solvate water molecules; three water molecules and two DDP O atoms via intermolecular H—O···H hydrogen bonds. A great number of hydrogen contacts link the complex into a three-dimensional network. (Fig. 2; for symmetry codes see Table 1).

Related literature top

For related literature, see: Zhao et al. (2007); Yin et al. (2007).

Experimental top

6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinic acid, and MnCl₂. 6H₂O were available commercially and were used without further purification. Equimolar 6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinic acid (1 mmol, 217 mg) was dissolved in anhydrous ethyl alcohol (AR,99.9%) (15 ml). The mixture was stirred to give a clear solution, To this solution was added MnCl₂.6H₂O (0.5 mmol, 119 mg) in anhydrous alcohol (10 ml). After keeping the resulting solution in air to evaporate about half of the solvents, yellow blocks of the title compound were formed. The crystals were isolated, washed with alcohol three times(Yield75%). Elemental analysis: found: C, 48.65; H, 5.01; O, 20.87; calc. for C₂₂H₂₆Mn_N6_O7: C, 48.80; H, 4.84; O, 20.69.

Structure description top

For related literature, see: Zhao et al. (2007); Yin et al. (2007).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top

	Fig. 1. The structure of the title compound (I) showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Crystal packing of (I) showing the hydrogen bonded interactions as dashed lines.

Bis[6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinato]manganese(II) trihydrate top

Crystal data top

[Mn(C₁₁H₁₀N₃O₂)₂]·3(H₂O)	Z = 2
M_r = 541.43	F(000) = 562
Triclinic, P1	D_x = 1.448 Mg m⁻³
a = 9.795 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.9030 (12) Å	Cell parameters from 2622 reflections
c = 12.8070 (15) Å	θ = 2.2–24.3°
α = 70.162 (2)°	µ = 0.59 mm⁻¹
β = 74.825 (2)°	T = 293 K
γ = 83.760 (3)°	Block, yellow
V = 1241.4 (2) Å³	0.53 × 0.49 × 0.47 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4308 independent reflections
Radiation source: fine-focus sealed tube	3050 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
phi and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.747, T_max = 0.770	k = −12→12
6455 measured reflections	l = −15→8

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0777P)² + 0.3474P] where P = (F_o² + 2F_c²)/3
4308 reflections	(Δ/σ)_max < 0.001
338 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

[Mn(C₁₁H₁₀N₃O₂)₂]·3(H₂O)	γ = 83.760 (3)°
M_r = 541.43	V = 1241.4 (2) Å³
Triclinic, P1	Z = 2
a = 9.795 (1) Å	Mo Kα radiation
b = 10.9030 (12) Å	µ = 0.59 mm⁻¹
c = 12.8070 (15) Å	T = 293 K
α = 70.162 (2)°	0.53 × 0.49 × 0.47 mm
β = 74.825 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4308 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3050 reflections with I > 2σ(I)
T_min = 0.747, T_max = 0.770	R_int = 0.024
6455 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.07	Δρ_max = 0.57 e Å⁻³
4308 reflections	Δρ_min = −0.25 e Å⁻³
338 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	Occ. (<1)
Mn1	0.71418 (5)	0.77632 (5)	0.27494 (5)	0.0466 (2)
N1	0.8241 (3)	0.9608 (2)	0.2282 (2)	0.0393 (6)
N2	0.7833 (3)	1.0148 (3)	0.0499 (2)	0.0446 (7)
N3	0.7221 (3)	0.8947 (3)	0.0899 (3)	0.0497 (7)
N4	0.6120 (3)	0.5904 (2)	0.3154 (2)	0.0392 (6)
N5	0.3986 (3)	0.6848 (3)	0.3745 (2)	0.0420 (7)
N6	0.4768 (3)	0.7939 (3)	0.3460 (2)	0.0444 (7)
O1	0.7731 (3)	0.7770 (3)	0.4245 (2)	0.0640 (8)
O2	0.8860 (3)	0.8766 (3)	0.5015 (2)	0.0624 (7)
O3	0.8791 (3)	0.6429 (3)	0.2293 (3)	0.0763 (9)
O4	0.9341 (3)	0.4450 (3)	0.2160 (3)	0.0884 (10)
O5	0.1776 (4)	0.3403 (4)	0.2963 (3)	0.1229 (15)
H5A	0.1559	0.2755	0.3571	0.147*
H5B	0.1027	0.3702	0.2738	0.147*
O6	0.4031 (5)	0.4792 (5)	0.1413 (4)	0.1482 (18)
H6A	0.3308	0.4374	0.1866	0.178*
H6B	0.3820	0.5237	0.0787	0.178*
O7	0.6528 (7)	0.3620 (7)	0.0713 (5)	0.091 (2)	0.50
H7D	0.5787	0.4047	0.0917	0.109*	0.50
H7E	0.7237	0.4108	0.0498	0.109*	0.50
O8	0.1259 (9)	0.5103 (8)	−0.0015 (6)	0.126 (3)	0.50
H8A	0.0580	0.4912	0.0579	0.151*	0.50
H8B	0.0936	0.5213	−0.0596	0.151*	0.50
C1	0.8435 (4)	0.8683 (3)	0.4221 (3)	0.0473 (9)
C2	0.8803 (3)	0.9762 (3)	0.3073 (3)	0.0411 (8)
C3	0.9641 (4)	1.0799 (3)	0.2834 (3)	0.0519 (9)
H3	1.0008	1.0911	0.3395	0.062*
C4	0.9924 (4)	1.1670 (3)	0.1738 (4)	0.0594 (11)
H4	1.0502	1.2372	0.1555	0.071*
C5	0.9367 (4)	1.1518 (3)	0.0912 (4)	0.0552 (10)
H5	0.9565	1.2098	0.0169	0.066*
C6	0.8496 (3)	1.0464 (3)	0.1233 (3)	0.0405 (8)
C7	0.8161 (5)	1.2156 (4)	−0.1267 (4)	0.0803 (14)
H7A	0.7824	1.2723	−0.0816	0.120*
H7B	0.7791	1.2456	−0.1937	0.120*
H7C	0.9176	1.2161	−0.1490	0.120*
C8	0.7683 (4)	1.0808 (4)	−0.0581 (3)	0.0549 (10)
C9	0.6970 (5)	1.0015 (4)	−0.0857 (4)	0.0656 (11)
H9	0.6703	1.0198	−0.1541	0.079*
C10	0.6709 (4)	0.8872 (4)	0.0073 (3)	0.0559 (10)
C11	0.6005 (5)	0.7670 (4)	0.0192 (4)	0.0819 (14)
H11A	0.6708	0.7055	−0.0019	0.123*
H11B	0.5363	0.7889	−0.0299	0.123*
H11C	0.5492	0.7291	0.0971	0.123*
C12	0.8506 (4)	0.5290 (4)	0.2427 (4)	0.0606 (10)
C13	0.6970 (4)	0.4915 (3)	0.2970 (3)	0.0460 (8)
C14	0.6473 (5)	0.3689 (3)	0.3275 (4)	0.0582 (10)
H14	0.7075	0.3009	0.3142	0.070*
C15	0.5062 (5)	0.3488 (4)	0.3784 (4)	0.0665 (12)
H15	0.4706	0.2655	0.4016	0.080*
C16	0.4175 (4)	0.4493 (3)	0.3953 (3)	0.0568 (10)
H16	0.3214	0.4366	0.4283	0.068*
C17	0.4754 (3)	0.5708 (3)	0.3617 (3)	0.0402 (8)
C18	0.1427 (4)	0.6136 (4)	0.4516 (4)	0.0638 (11)
H18A	0.0528	0.6560	0.4699	0.096*
H18B	0.1554	0.5423	0.5176	0.096*
H18C	0.1458	0.5812	0.3901	0.096*
C19	0.2586 (4)	0.7093 (4)	0.4162 (3)	0.0477 (9)
C20	0.2486 (4)	0.8342 (4)	0.4157 (3)	0.0524 (9)
H20	0.1664	0.8784	0.4402	0.063*
C21	0.3839 (4)	0.8842 (3)	0.3718 (3)	0.0479 (9)
C22	0.4326 (5)	1.0165 (4)	0.3515 (4)	0.0681 (12)
H22A	0.4185	1.0314	0.4234	0.102*
H22B	0.3794	1.0806	0.3045	0.102*
H22C	0.5313	1.0231	0.3136	0.102*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0390 (3)	0.0378 (3)	0.0600 (4)	−0.0121 (2)	−0.0096 (3)	−0.0103 (2)
N1	0.0341 (15)	0.0344 (14)	0.0472 (17)	−0.0064 (11)	−0.0079 (13)	−0.0103 (13)
N2	0.0423 (16)	0.0408 (15)	0.0466 (18)	−0.0084 (12)	−0.0089 (13)	−0.0081 (13)
N3	0.0523 (18)	0.0414 (16)	0.0567 (19)	−0.0142 (13)	−0.0139 (15)	−0.0131 (14)
N4	0.0398 (16)	0.0349 (14)	0.0423 (16)	−0.0043 (12)	−0.0094 (13)	−0.0111 (12)
N5	0.0324 (15)	0.0432 (15)	0.0502 (17)	−0.0079 (12)	−0.0081 (13)	−0.0142 (13)
N6	0.0424 (16)	0.0361 (14)	0.0558 (18)	−0.0077 (12)	−0.0109 (14)	−0.0149 (13)
O1	0.0644 (18)	0.0632 (16)	0.0582 (17)	−0.0303 (13)	−0.0210 (14)	0.0016 (13)
O2	0.0605 (17)	0.0727 (18)	0.0581 (17)	−0.0093 (13)	−0.0234 (14)	−0.0170 (14)
O3	0.0387 (15)	0.0537 (17)	0.120 (3)	−0.0087 (12)	0.0034 (16)	−0.0222 (17)
O4	0.071 (2)	0.070 (2)	0.108 (3)	0.0221 (17)	−0.0015 (18)	−0.0313 (19)
O5	0.084 (3)	0.144 (3)	0.108 (3)	−0.040 (2)	−0.045 (2)	0.028 (2)
O6	0.126 (4)	0.177 (5)	0.114 (3)	−0.021 (3)	−0.015 (3)	−0.017 (3)
O7	0.081 (4)	0.142 (6)	0.066 (4)	0.037 (4)	−0.023 (3)	−0.062 (4)
O8	0.145 (7)	0.129 (7)	0.061 (4)	0.021 (6)	0.007 (5)	−0.010 (4)
C1	0.0324 (18)	0.054 (2)	0.054 (2)	−0.0042 (15)	−0.0106 (17)	−0.0144 (18)
C2	0.0322 (17)	0.0385 (17)	0.055 (2)	0.0022 (13)	−0.0122 (16)	−0.0177 (16)
C3	0.050 (2)	0.0410 (19)	0.074 (3)	−0.0029 (16)	−0.023 (2)	−0.0244 (19)
C4	0.063 (3)	0.0334 (18)	0.083 (3)	−0.0141 (17)	−0.024 (2)	−0.0111 (19)
C5	0.056 (2)	0.0367 (19)	0.067 (3)	−0.0109 (16)	−0.017 (2)	−0.0050 (18)
C6	0.0348 (18)	0.0354 (17)	0.049 (2)	−0.0029 (13)	−0.0084 (15)	−0.0116 (15)
C7	0.092 (4)	0.076 (3)	0.058 (3)	−0.033 (3)	−0.023 (3)	0.010 (2)
C8	0.052 (2)	0.057 (2)	0.048 (2)	−0.0097 (18)	−0.0058 (18)	−0.0100 (18)
C9	0.071 (3)	0.079 (3)	0.050 (2)	−0.011 (2)	−0.019 (2)	−0.017 (2)
C10	0.055 (2)	0.059 (2)	0.059 (2)	−0.0113 (18)	−0.017 (2)	−0.021 (2)
C11	0.097 (4)	0.075 (3)	0.089 (3)	−0.025 (3)	−0.037 (3)	−0.027 (3)
C12	0.055 (2)	0.053 (2)	0.061 (3)	0.0065 (19)	−0.005 (2)	−0.011 (2)
C13	0.050 (2)	0.0394 (18)	0.045 (2)	0.0019 (16)	−0.0124 (17)	−0.0092 (15)
C14	0.073 (3)	0.0379 (19)	0.070 (3)	0.0035 (18)	−0.023 (2)	−0.0216 (18)
C15	0.080 (3)	0.040 (2)	0.083 (3)	−0.019 (2)	−0.021 (2)	−0.018 (2)
C16	0.054 (2)	0.048 (2)	0.068 (3)	−0.0198 (18)	−0.012 (2)	−0.0146 (19)
C17	0.0403 (19)	0.0407 (18)	0.0412 (19)	−0.0100 (14)	−0.0101 (15)	−0.0123 (15)
C18	0.036 (2)	0.072 (3)	0.071 (3)	−0.0153 (18)	−0.0052 (19)	−0.010 (2)
C19	0.037 (2)	0.059 (2)	0.043 (2)	−0.0054 (16)	−0.0095 (16)	−0.0101 (17)
C20	0.041 (2)	0.059 (2)	0.053 (2)	0.0059 (17)	−0.0089 (17)	−0.0160 (18)
C21	0.047 (2)	0.0443 (19)	0.053 (2)	0.0033 (16)	−0.0162 (17)	−0.0159 (17)
C22	0.067 (3)	0.048 (2)	0.096 (3)	0.0025 (19)	−0.021 (2)	−0.032 (2)

Geometric parameters (Å, º) top

Mn1—O1	2.143 (3)	C4—C5	1.373 (5)
Mn1—O3	2.154 (3)	C4—H4	0.9300
Mn1—N4	2.199 (3)	C5—C6	1.388 (4)
Mn1—N1	2.209 (2)	C5—H5	0.9300
Mn1—N3	2.267 (3)	C7—C8	1.486 (5)
Mn1—N6	2.277 (3)	C7—H7A	0.9600
N1—C6	1.327 (4)	C7—H7B	0.9600
N1—C2	1.336 (4)	C7—H7C	0.9600
N2—C8	1.364 (5)	C8—C9	1.353 (5)
N2—N3	1.375 (4)	C9—C10	1.393 (6)
N2—C6	1.419 (4)	C9—H9	0.9300
N3—C10	1.311 (5)	C10—C11	1.491 (5)
N4—C17	1.322 (4)	C11—H11A	0.9600
N4—C13	1.336 (4)	C11—H11B	0.9600
N5—C19	1.368 (4)	C11—H11C	0.9600
N5—N6	1.375 (3)	C12—C13	1.519 (5)
N5—C17	1.416 (4)	C13—C14	1.365 (5)
N6—C21	1.332 (4)	C14—C15	1.371 (6)
O1—C1	1.259 (4)	C14—H14	0.9300
O2—C1	1.227 (4)	C15—C16	1.364 (5)
O3—C12	1.247 (5)	C15—H15	0.9300
O4—C12	1.235 (5)	C16—C17	1.382 (4)
O5—H5A	0.8500	C16—H16	0.9300
O5—H5B	0.8500	C18—C19	1.500 (5)
O6—H6A	0.8500	C18—H18A	0.9600
O6—H6B	0.8500	C18—H18B	0.9600
O7—H7D	0.8499	C18—H18C	0.9600
O7—H7E	0.8500	C19—C20	1.353 (5)
O8—H8A	0.8500	C20—C21	1.389 (5)
O8—H8B	0.8500	C20—H20	0.9300
C1—C2	1.522 (5)	C21—C22	1.486 (5)
C2—C3	1.372 (5)	C22—H22A	0.9600
C3—C4	1.377 (5)	C22—H22B	0.9600
C3—H3	0.9300	C22—H22C	0.9600

O1—Mn1—O3	96.39 (13)	H7A—C7—H7B	109.5
O1—Mn1—N4	108.16 (10)	C8—C7—H7C	109.5
O3—Mn1—N4	73.44 (10)	H7A—C7—H7C	109.5
O1—Mn1—N1	73.16 (10)	H7B—C7—H7C	109.5
O3—Mn1—N1	104.29 (10)	C9—C8—N2	106.2 (3)
N4—Mn1—N1	177.41 (10)	C9—C8—C7	128.3 (4)
O1—Mn1—N3	143.23 (10)	N2—C8—C7	125.5 (4)
O3—Mn1—N3	92.96 (12)	C8—C9—C10	107.2 (4)
N4—Mn1—N3	108.59 (10)	C8—C9—H9	126.4
N1—Mn1—N3	70.08 (10)	C10—C9—H9	126.4
O1—Mn1—N6	95.74 (11)	N3—C10—C9	110.2 (3)
O3—Mn1—N6	142.92 (10)	N3—C10—C11	121.0 (4)
N4—Mn1—N6	69.49 (10)	C9—C10—C11	128.8 (4)
N1—Mn1—N6	112.76 (9)	C10—C11—H11A	109.5
N3—Mn1—N6	97.89 (11)	C10—C11—H11B	109.5
C6—N1—C2	120.1 (3)	H11A—C11—H11B	109.5
C6—N1—Mn1	122.8 (2)	C10—C11—H11C	109.5
C2—N1—Mn1	116.5 (2)	H11A—C11—H11C	109.5
C8—N2—N3	110.3 (3)	H11B—C11—H11C	109.5
C8—N2—C6	132.4 (3)	O4—C12—O3	126.6 (4)
N3—N2—C6	117.2 (3)	O4—C12—C13	117.5 (4)
C10—N3—N2	106.0 (3)	O3—C12—C13	115.9 (3)
C10—N3—Mn1	137.2 (2)	N4—C13—C14	121.7 (3)
N2—N3—Mn1	116.4 (2)	N4—C13—C12	113.6 (3)
C17—N4—C13	119.7 (3)	C14—C13—C12	124.6 (3)
C17—N4—Mn1	123.7 (2)	C13—C14—C15	118.2 (4)
C13—N4—Mn1	116.5 (2)	C13—C14—H14	120.9
C19—N5—N6	110.6 (3)	C15—C14—H14	120.9
C19—N5—C17	133.0 (3)	C16—C15—C14	120.8 (3)
N6—N5—C17	116.4 (2)	C16—C15—H15	119.6
C21—N6—N5	105.3 (3)	C14—C15—H15	119.6
C21—N6—Mn1	137.7 (2)	C15—C16—C17	117.7 (4)
N5—N6—Mn1	116.96 (19)	C15—C16—H16	121.1
C1—O1—Mn1	121.2 (2)	C17—C16—H16	121.1
C12—O3—Mn1	120.3 (2)	N4—C17—C16	121.9 (3)
H5A—O5—H5B	108.4	N4—C17—N5	113.3 (3)
H6A—O6—H6B	108.5	C16—C17—N5	124.8 (3)
H7D—O7—H7E	108.6	C19—C18—H18A	109.5
H8A—O8—H8B	108.7	C19—C18—H18B	109.5
O2—C1—O1	126.6 (3)	H18A—C18—H18B	109.5
O2—C1—C2	118.3 (3)	C19—C18—H18C	109.5
O1—C1—C2	115.1 (3)	H18A—C18—H18C	109.5
N1—C2—C3	121.5 (3)	H18B—C18—H18C	109.5
N1—C2—C1	113.6 (3)	C20—C19—N5	106.5 (3)
C3—C2—C1	124.9 (3)	C20—C19—C18	128.6 (3)
C2—C3—C4	118.1 (3)	N5—C19—C18	124.9 (3)
C2—C3—H3	121.0	C19—C20—C21	107.2 (3)
C4—C3—H3	121.0	C19—C20—H20	126.4
C5—C4—C3	121.1 (3)	C21—C20—H20	126.4
C5—C4—H4	119.4	N6—C21—C20	110.4 (3)
C3—C4—H4	119.4	N6—C21—C22	119.9 (3)
C4—C5—C6	117.2 (3)	C20—C21—C22	129.6 (3)
C4—C5—H5	121.4	C21—C22—H22A	109.5
C6—C5—H5	121.4	C21—C22—H22B	109.5
N1—C6—C5	121.9 (3)	H22A—C22—H22B	109.5
N1—C6—N2	112.8 (3)	C21—C22—H22C	109.5
C5—C6—N2	125.2 (3)	H22A—C22—H22C	109.5
C8—C7—H7A	109.5	H22B—C22—H22C	109.5
C8—C7—H7B	109.5

O1—Mn1—N1—C6	177.3 (3)	O1—C1—C2—N1	3.9 (4)
O3—Mn1—N1—C6	84.8 (3)	O2—C1—C2—C3	3.5 (5)
N4—Mn1—N1—C6	56 (2)	O1—C1—C2—C3	−175.3 (3)
N3—Mn1—N1—C6	−3.1 (2)	N1—C2—C3—C4	−1.7 (5)
N6—Mn1—N1—C6	−93.5 (3)	C1—C2—C3—C4	177.4 (3)
O1—Mn1—N1—C2	5.3 (2)	C2—C3—C4—C5	1.0 (6)
O3—Mn1—N1—C2	−87.1 (2)	C3—C4—C5—C6	0.8 (6)
N4—Mn1—N1—C2	−116 (2)	C2—N1—C6—C5	1.5 (5)
N3—Mn1—N1—C2	−175.1 (3)	Mn1—N1—C6—C5	−170.2 (3)
N6—Mn1—N1—C2	94.5 (2)	C2—N1—C6—N2	179.3 (3)
C8—N2—N3—C10	0.3 (4)	Mn1—N1—C6—N2	7.6 (4)
C6—N2—N3—C10	−178.9 (3)	C4—C5—C6—N1	−2.1 (5)
C8—N2—N3—Mn1	−173.8 (2)	C4—C5—C6—N2	−179.7 (3)
C6—N2—N3—Mn1	7.0 (4)	C8—N2—C6—N1	171.8 (3)
O1—Mn1—N3—C10	−173.2 (3)	N3—N2—C6—N1	−9.3 (4)
O3—Mn1—N3—C10	82.0 (4)	C8—N2—C6—C5	−10.5 (6)
N4—Mn1—N3—C10	8.5 (4)	N3—N2—C6—C5	168.5 (3)
N1—Mn1—N3—C10	−173.9 (4)	N3—N2—C8—C9	0.1 (4)
N6—Mn1—N3—C10	−62.5 (4)	C6—N2—C8—C9	179.1 (3)
O1—Mn1—N3—N2	−1.6 (3)	N3—N2—C8—C7	177.4 (4)
O3—Mn1—N3—N2	−106.4 (2)	C6—N2—C8—C7	−3.6 (6)
N4—Mn1—N3—N2	−179.9 (2)	N2—C8—C9—C10	−0.4 (5)
N1—Mn1—N3—N2	−2.3 (2)	C7—C8—C9—C10	−177.6 (4)
N6—Mn1—N3—N2	109.2 (2)	N2—N3—C10—C9	−0.5 (4)
O1—Mn1—N4—C17	87.0 (3)	Mn1—N3—C10—C9	171.7 (3)
O3—Mn1—N4—C17	178.4 (3)	N2—N3—C10—C11	177.8 (4)
N1—Mn1—N4—C17	−153 (2)	Mn1—N3—C10—C11	−10.0 (6)
N3—Mn1—N4—C17	−94.1 (3)	C8—C9—C10—N3	0.6 (5)
N6—Mn1—N4—C17	−2.5 (2)	C8—C9—C10—C11	−177.6 (4)
O1—Mn1—N4—C13	−89.2 (2)	Mn1—O3—C12—O4	177.1 (4)
O3—Mn1—N4—C13	2.2 (2)	Mn1—O3—C12—C13	−2.7 (5)
N1—Mn1—N4—C13	31 (2)	C17—N4—C13—C14	−1.8 (5)
N3—Mn1—N4—C13	89.7 (2)	Mn1—N4—C13—C14	174.6 (3)
N6—Mn1—N4—C13	−178.6 (3)	C17—N4—C13—C12	179.6 (3)
C19—N5—N6—C21	0.7 (4)	Mn1—N4—C13—C12	−4.1 (4)
C17—N5—N6—C21	−176.2 (3)	O4—C12—C13—N4	−175.3 (4)
C19—N5—N6—Mn1	179.8 (2)	O3—C12—C13—N4	4.5 (5)
C17—N5—N6—Mn1	2.9 (3)	O4—C12—C13—C14	6.1 (6)
O1—Mn1—N6—C21	71.0 (4)	O3—C12—C13—C14	−174.1 (4)
O3—Mn1—N6—C21	179.6 (3)	N4—C13—C14—C15	0.0 (6)
N4—Mn1—N6—C21	178.2 (4)	C12—C13—C14—C15	178.4 (4)
N1—Mn1—N6—C21	−3.1 (4)	C13—C14—C15—C16	1.6 (6)
N3—Mn1—N6—C21	−74.8 (4)	C14—C15—C16—C17	−1.3 (6)
O1—Mn1—N6—N5	−107.7 (2)	C13—N4—C17—C16	2.1 (5)
O3—Mn1—N6—N5	0.9 (3)	Mn1—N4—C17—C16	−174.0 (3)
N4—Mn1—N6—N5	−0.4 (2)	C13—N4—C17—N5	−179.2 (3)
N1—Mn1—N6—N5	178.2 (2)	Mn1—N4—C17—N5	4.7 (4)
N3—Mn1—N6—N5	106.6 (2)	C15—C16—C17—N4	−0.5 (6)
O3—Mn1—O1—C1	99.9 (3)	C15—C16—C17—N5	−179.1 (3)
N4—Mn1—O1—C1	174.5 (3)	C19—N5—C17—N4	179.2 (3)
N1—Mn1—O1—C1	−3.2 (3)	N6—N5—C17—N4	−4.7 (4)
N3—Mn1—O1—C1	−3.8 (4)	C19—N5—C17—C16	−2.1 (6)
N6—Mn1—O1—C1	−115.3 (3)	N6—N5—C17—C16	173.9 (3)
O1—Mn1—O3—C12	107.5 (3)	N6—N5—C19—C20	−1.0 (4)
N4—Mn1—O3—C12	0.5 (3)	C17—N5—C19—C20	175.2 (3)
N1—Mn1—O3—C12	−178.3 (3)	N6—N5—C19—C18	177.7 (3)
N3—Mn1—O3—C12	−108.1 (3)	C17—N5—C19—C18	−6.1 (6)
N6—Mn1—O3—C12	−0.8 (5)	N5—C19—C20—C21	0.8 (4)
Mn1—O1—C1—O2	−177.9 (3)	C18—C19—C20—C21	−177.8 (4)
Mn1—O1—C1—C2	0.8 (4)	N5—N6—C21—C20	−0.2 (4)
C6—N1—C2—C3	0.5 (5)	Mn1—N6—C21—C20	−179.0 (3)
Mn1—N1—C2—C3	172.7 (2)	N5—N6—C21—C22	−179.9 (3)
C6—N1—C2—C1	−178.8 (3)	Mn1—N6—C21—C22	1.4 (6)
Mn1—N1—C2—C1	−6.6 (3)	C19—C20—C21—N6	−0.4 (4)
O2—C1—C2—N1	−177.3 (3)	C19—C20—C21—C22	179.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2ⁱ	0.85	1.98	2.830 (4)	178
O5—H5B···O4ⁱⁱ	0.85	1.97	2.819 (5)	178
O6—H6A···O5	0.85	1.89	2.740 (6)	176
O6—H6B···O7ⁱⁱⁱ	0.85	2.00	2.843 (8)	175
O7—H7D···O6	0.85	1.87	2.715 (8)	173
O7—H7E···O8ⁱⁱⁱ	0.85	1.65	2.497 (12)	172
O8—H8A···O4ⁱⁱ	0.85	2.00	2.829 (8)	167
O8—H8B···O4ⁱⁱⁱ	0.85	2.00	2.829 (9)	166

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

Experimental details

Crystal data
Chemical formula	[Mn(C₁₁H₁₀N₃O₂)₂]·3(H₂O)
M_r	541.43
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.795 (1), 10.9030 (12), 12.8070 (15)
α, β, γ (°)	70.162 (2), 74.825 (2), 83.760 (3)
V (Å³)	1241.4 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.53 × 0.49 × 0.47

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.747, 0.770
No. of measured, independent and observed [I > 2σ(I)] reflections	6455, 4308, 3050
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.150, 1.07
No. of reflections	4308
No. of parameters	338
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.25

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2ⁱ	0.85	1.98	2.830 (4)	177.6
O5—H5B···O4ⁱⁱ	0.85	1.97	2.819 (5)	177.6
O6—H6A···O5	0.85	1.89	2.740 (6)	175.5
O6—H6B···O7ⁱⁱⁱ	0.85	2.00	2.843 (8)	174.8
O7—H7D···O6	0.85	1.87	2.715 (8)	172.6
O7—H7E···O8ⁱⁱⁱ	0.85	1.65	2.497 (12)	172.0
O8—H8A···O4ⁱⁱ	0.85	2.00	2.829 (8)	166.5
O8—H8B···O4ⁱⁱⁱ	0.85	2.00	2.829 (9)	166.3

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

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page