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The title compound, [Mn(C7H5O3)(C12H8N2)2(H2O)](C7H5O3)·H2O, consists of MnII complex cations, 4-hydroxy­benzoate anions and uncoordinated water mol­ecules. The MnII complex cation assumes a distorted octa­hedral coordination geometry formed by two 1,10-phenanthroline (phen) ligands, one 4-hydroxy­benzoate anion and a water mol­ecule. The face-to-face distances of 3.39 (2) and 3.364 (12) Å between partially overlapped parallel phen ligands suggest the existence of π–π stacking between neighboring complex cations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805011694/hb6182sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805011694/hb6182Isup2.hkl
Contains datablock I

CCDC reference: 271885

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.046
  • wR factor = 0.088
  • Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT230_ALERT_2_C Hirshfeld Test Diff for O41 - C41 .. 5.94 su PLAT417_ALERT_2_C Short Inter D-H..H-D H1 .. H1B .. 2.13 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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

(I) top
Crystal data top
[Mn(C7H5O3)(C12H8N2)2(H2O)](C7H5O3)·H2OF(000) = 1500
Mr = 725.60Dx = 1.421 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ynCell parameters from 10848 reflections
a = 8.4429 (2) Åθ = 2.6–24.6°
b = 24.1805 (6) ŵ = 0.45 mm1
c = 17.0825 (4) ÅT = 295 K
β = 103.495 (7)°Platelet, yellow
V = 3391.17 (17) Å30.20 × 0.20 × 0.05 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
5716 independent reflections
Radiation source: fine-focus sealed tube3936 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
Detector resolution: 10.0 pixels mm-1θmax = 25.0°, θmin = 1.5°
ω scansh = 910
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 2728
Tmin = 0.916, Tmax = 0.979l = 2020
22265 measured reflections
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0343P)2 + 2.0463P]
where P = (Fo2 + 2Fc2)/3
5716 reflections(Δ/σ)max = 0.001
460 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.28 e Å3
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
Mn0.56565 (5)0.515174 (17)0.26354 (2)0.03630 (12)
O10.3644 (2)0.57001 (8)0.21977 (12)0.0551 (6)
H20.26150.55210.20150.080*
H10.36020.60440.19600.080*
O1W0.3859 (3)0.66856 (9)0.15367 (16)0.0849 (8)
H1A0.35440.68860.10600.080*
H1B0.44130.68820.20250.080*
O310.3935 (2)0.45113 (7)0.25506 (11)0.0432 (5)
O320.1597 (2)0.48725 (8)0.18525 (13)0.0555 (5)
O330.0393 (2)0.23500 (8)0.19446 (13)0.0623 (6)
H330.13890.24010.16010.080*
O410.3231 (2)0.77098 (10)0.09951 (15)0.0730 (7)
O420.2927 (2)0.73574 (10)0.01651 (14)0.0670 (7)
O431.0606 (2)0.76340 (9)0.08896 (14)0.0644 (6)
H431.10280.75710.04190.080*
N10.6285 (3)0.48399 (10)0.14823 (13)0.0435 (6)
N20.7448 (3)0.57659 (9)0.23314 (13)0.0400 (6)
N30.7569 (2)0.46291 (8)0.34584 (13)0.0364 (5)
N40.5930 (2)0.54837 (9)0.39067 (13)0.0365 (5)
C10.5707 (3)0.43923 (13)0.10690 (19)0.0543 (8)
H40.50550.41520.12810.065*
C20.6040 (4)0.42659 (15)0.0321 (2)0.0623 (10)
H70.56230.39460.00460.075*
C30.6981 (4)0.46178 (16)0.0004 (2)0.0650 (10)
H30.71900.45420.04960.078*
C40.7635 (3)0.50901 (14)0.04206 (17)0.0513 (8)
C50.8648 (4)0.54778 (16)0.0132 (2)0.0668 (10)
H50.88690.54230.03700.080*
C60.9280 (4)0.59158 (16)0.0567 (2)0.0695 (11)
H60.99390.61580.03620.083*
C70.8974 (3)0.60247 (13)0.13419 (19)0.0509 (8)
C80.9627 (4)0.64704 (14)0.1834 (2)0.0628 (10)
H81.03720.67050.16800.075*
C90.9177 (4)0.65629 (13)0.2537 (2)0.0609 (9)
H90.96070.68590.28660.073*
C100.8065 (3)0.62072 (12)0.27535 (19)0.0486 (7)
H100.77320.62830.32240.058*
C110.7901 (3)0.56704 (12)0.16310 (17)0.0423 (7)
C120.7257 (3)0.51875 (13)0.11729 (16)0.0431 (7)
C130.8438 (3)0.42251 (12)0.32378 (19)0.0476 (8)
H130.83290.41630.26910.057*
C140.9496 (4)0.38925 (12)0.3778 (2)0.0541 (8)
H141.01030.36210.35960.065*
C150.9635 (3)0.39682 (12)0.4580 (2)0.0532 (8)
H151.03160.37390.49490.064*
C160.8756 (3)0.43899 (11)0.48532 (18)0.0411 (7)
C170.8833 (3)0.45068 (13)0.56804 (18)0.0513 (8)
H170.94720.42850.60750.062*
C180.8005 (3)0.49297 (13)0.59015 (17)0.0507 (8)
H180.80840.49960.64460.061*
C190.7009 (3)0.52787 (11)0.53175 (16)0.0380 (7)
C200.6162 (3)0.57362 (13)0.55223 (19)0.0502 (8)
H200.62210.58210.60590.060*
C210.5253 (4)0.60530 (13)0.49247 (19)0.0513 (8)
H210.47010.63610.50500.062*
C220.5156 (3)0.59133 (12)0.41277 (18)0.0455 (7)
H220.45160.61320.37280.055*
C230.6870 (3)0.51709 (11)0.45030 (15)0.0326 (6)
C240.7743 (3)0.47154 (10)0.42582 (16)0.0329 (6)
C310.2453 (3)0.44722 (11)0.21614 (16)0.0383 (6)
C320.1717 (3)0.39085 (10)0.20897 (15)0.0337 (6)
C330.2557 (3)0.34556 (11)0.24790 (16)0.0405 (7)
H320.36200.35010.27780.049*
C340.1843 (3)0.29402 (11)0.24305 (17)0.0464 (7)
H340.24220.26420.26980.056*
C350.0261 (3)0.28676 (11)0.19825 (18)0.0434 (7)
C360.0589 (3)0.33150 (11)0.15809 (17)0.0429 (7)
H360.16450.32690.12740.052*
C370.0138 (3)0.38254 (11)0.16391 (16)0.0387 (7)
H370.04400.41240.13700.046*
C410.3772 (3)0.75315 (12)0.0302 (2)0.0517 (8)
C420.5599 (3)0.75291 (11)0.00125 (19)0.0429 (7)
C430.6629 (3)0.74894 (13)0.0511 (2)0.0540 (8)
H420.61870.74460.10600.065*
C440.8307 (3)0.75138 (13)0.0229 (2)0.0549 (8)
H440.89810.74750.05850.066*
C450.8969 (3)0.75948 (12)0.0570 (2)0.0459 (7)
C460.7965 (3)0.76391 (11)0.11065 (19)0.0482 (7)
H460.84110.76960.16520.058*
C470.6300 (3)0.75980 (11)0.08211 (19)0.0452 (7)
H470.56330.76170.11830.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn0.0392 (2)0.0411 (2)0.0282 (2)0.0026 (2)0.00700 (17)0.0014 (2)
O10.0494 (11)0.0422 (12)0.0649 (16)0.0025 (9)0.0047 (10)0.0131 (10)
O1W0.0990 (18)0.0554 (14)0.085 (2)0.0169 (13)0.0095 (15)0.0235 (14)
O310.0382 (11)0.0467 (11)0.0403 (12)0.0061 (9)0.0002 (9)0.0004 (9)
O320.0525 (11)0.0425 (11)0.0616 (14)0.0013 (10)0.0066 (10)0.0059 (11)
O330.0522 (12)0.0437 (12)0.0747 (17)0.0083 (10)0.0180 (11)0.0124 (11)
O410.0460 (12)0.0908 (18)0.0679 (18)0.0175 (12)0.0155 (11)0.0315 (14)
O420.0389 (12)0.0879 (17)0.0714 (18)0.0036 (11)0.0072 (12)0.0169 (14)
O430.0348 (11)0.0904 (17)0.0613 (16)0.0014 (11)0.0027 (10)0.0099 (13)
N10.0446 (13)0.0508 (14)0.0335 (14)0.0016 (12)0.0058 (11)0.0033 (13)
N20.0435 (13)0.0450 (14)0.0313 (14)0.0025 (11)0.0082 (11)0.0042 (11)
N30.0368 (12)0.0386 (13)0.0342 (14)0.0001 (10)0.0092 (10)0.0057 (11)
N40.0386 (12)0.0379 (13)0.0339 (13)0.0008 (11)0.0105 (10)0.0039 (11)
C10.0484 (18)0.062 (2)0.049 (2)0.0085 (16)0.0033 (15)0.0112 (17)
C20.060 (2)0.075 (2)0.042 (2)0.0212 (19)0.0089 (16)0.0229 (18)
C30.063 (2)0.096 (3)0.0322 (18)0.031 (2)0.0038 (16)0.009 (2)
C40.0492 (17)0.076 (2)0.0264 (15)0.0276 (17)0.0040 (13)0.0093 (17)
C50.075 (2)0.089 (3)0.046 (2)0.031 (2)0.0347 (19)0.023 (2)
C60.073 (2)0.078 (3)0.070 (3)0.027 (2)0.041 (2)0.030 (2)
C70.0490 (18)0.056 (2)0.053 (2)0.0156 (16)0.0218 (16)0.0209 (17)
C80.055 (2)0.053 (2)0.084 (3)0.0004 (17)0.024 (2)0.020 (2)
C90.058 (2)0.0469 (19)0.077 (3)0.0079 (16)0.0154 (19)0.0035 (18)
C100.0521 (18)0.0460 (18)0.0475 (19)0.0005 (15)0.0115 (15)0.0019 (15)
C110.0420 (15)0.0488 (17)0.0355 (17)0.0125 (14)0.0081 (13)0.0115 (14)
C120.0421 (15)0.0615 (19)0.0250 (14)0.0201 (15)0.0063 (12)0.0094 (15)
C130.0513 (17)0.0475 (18)0.046 (2)0.0004 (15)0.0155 (15)0.0097 (15)
C140.0551 (19)0.0441 (18)0.065 (2)0.0077 (15)0.0171 (18)0.0031 (17)
C150.0447 (17)0.0416 (18)0.069 (3)0.0034 (14)0.0053 (17)0.0142 (17)
C160.0358 (14)0.0394 (16)0.0470 (19)0.0047 (13)0.0074 (13)0.0073 (14)
C170.0490 (17)0.065 (2)0.0349 (19)0.0063 (16)0.0001 (14)0.0146 (16)
C180.0519 (17)0.071 (2)0.0277 (16)0.0114 (16)0.0066 (14)0.0005 (15)
C190.0370 (14)0.0520 (18)0.0245 (15)0.0100 (13)0.0059 (12)0.0038 (13)
C200.0567 (19)0.060 (2)0.0372 (19)0.0132 (16)0.0179 (15)0.0163 (16)
C210.062 (2)0.0478 (19)0.047 (2)0.0002 (15)0.0200 (17)0.0150 (16)
C220.0506 (17)0.0421 (17)0.0436 (19)0.0056 (14)0.0103 (15)0.0010 (14)
C230.0336 (13)0.0366 (14)0.0279 (14)0.0091 (13)0.0074 (11)0.0010 (13)
C240.0312 (13)0.0349 (15)0.0330 (15)0.0074 (11)0.0082 (12)0.0015 (12)
C310.0443 (16)0.0468 (17)0.0242 (15)0.0006 (14)0.0088 (12)0.0016 (13)
C320.0349 (14)0.0391 (15)0.0269 (15)0.0016 (12)0.0066 (12)0.0023 (12)
C330.0340 (14)0.0465 (17)0.0352 (16)0.0008 (13)0.0035 (12)0.0027 (13)
C340.0437 (16)0.0393 (17)0.0473 (19)0.0016 (14)0.0073 (14)0.0044 (14)
C350.0405 (16)0.0389 (16)0.0463 (19)0.0024 (13)0.0010 (14)0.0020 (14)
C360.0346 (14)0.0499 (18)0.0381 (17)0.0020 (13)0.0044 (12)0.0012 (14)
C370.0391 (15)0.0380 (16)0.0373 (17)0.0058 (13)0.0056 (13)0.0053 (13)
C410.0399 (17)0.0415 (17)0.069 (3)0.0069 (14)0.0026 (17)0.0032 (17)
C420.0396 (15)0.0383 (16)0.0476 (19)0.0029 (13)0.0038 (14)0.0021 (14)
C430.0458 (17)0.070 (2)0.0406 (19)0.0053 (16)0.0022 (15)0.0007 (16)
C440.0413 (17)0.076 (2)0.047 (2)0.0021 (16)0.0098 (15)0.0022 (17)
C450.0351 (16)0.0448 (17)0.052 (2)0.0012 (13)0.0009 (14)0.0095 (15)
C460.0486 (18)0.0500 (18)0.0409 (19)0.0012 (14)0.0003 (15)0.0009 (15)
C470.0423 (16)0.0409 (17)0.053 (2)0.0009 (13)0.0119 (15)0.0019 (15)
Geometric parameters (Å, º) top
Mn—O12.1471 (19)C10—H100.93
Mn—O312.1054 (17)C11—C121.440 (4)
Mn—N12.284 (2)C13—C141.383 (4)
Mn—N22.265 (2)C13—H130.93
Mn—N32.263 (2)C14—C151.359 (4)
Mn—N42.276 (2)C14—H140.93
O1—H20.9562C15—C161.404 (4)
O1—H10.9224C15—H150.93
O1W—H1A0.9318C16—C241.407 (4)
O1W—H1B0.9779C16—C171.428 (4)
C31—O311.276 (3)C17—C181.342 (4)
C31—O321.249 (3)C17—H170.93
O33—C351.363 (3)C18—C191.422 (4)
O33—H330.9149C18—H180.93
C41—O411.243 (4)C19—C231.393 (3)
C41—O421.260 (4)C19—C201.405 (4)
O43—C451.366 (3)C20—C211.361 (4)
O43—H430.9650C20—H200.93
N1—C11.322 (4)C21—C221.386 (4)
N1—C121.365 (3)C21—H210.93
N2—C101.325 (3)C22—H220.93
N2—C111.359 (3)C23—C241.441 (3)
N3—C131.328 (3)C31—C321.491 (4)
N3—C241.356 (3)C32—C331.387 (3)
N4—C221.328 (3)C32—C371.390 (3)
N4—C231.365 (3)C33—C341.378 (4)
C1—C21.404 (4)C33—H320.93
C1—H40.93C34—C351.388 (4)
C2—C31.360 (5)C34—H340.93
C2—H70.93C35—C361.388 (4)
C3—C41.390 (5)C36—C371.372 (3)
C3—H30.93C36—H360.93
C4—C121.414 (4)C37—H370.93
C4—C51.431 (4)C41—C421.510 (4)
C5—C61.332 (5)C42—C471.380 (4)
C5—H50.93C42—C431.389 (4)
C6—C71.430 (4)C43—C441.387 (4)
C6—H60.93C43—H420.93
C7—C81.398 (4)C44—C451.362 (4)
C7—C111.417 (4)C44—H440.93
C8—C91.360 (5)C45—C461.390 (4)
C8—H80.93C46—C471.380 (4)
C9—C101.385 (4)C46—H460.93
C9—H90.93C47—H470.93
O1—Mn—O3187.31 (7)C15—C14—H14120.5
O1—Mn—N1103.17 (8)C13—C14—H14120.5
O1—Mn—N291.81 (8)C14—C15—C16120.3 (3)
O1—Mn—N3162.37 (8)C14—C15—H15119.8
O1—Mn—N490.58 (8)C16—C15—H15119.8
O31—Mn—N189.62 (8)C15—C16—C24116.5 (3)
O31—Mn—N2162.49 (8)C15—C16—C17124.6 (3)
O31—Mn—N390.73 (7)C24—C16—C17118.9 (3)
O31—Mn—N4103.87 (7)C18—C17—C16121.6 (3)
N1—Mn—N273.54 (8)C18—C17—H17119.2
N1—Mn—N394.34 (8)C16—C17—H17119.2
N1—Mn—N4161.26 (8)C17—C18—C19121.1 (3)
N2—Mn—N395.22 (7)C17—C18—H18119.5
N2—Mn—N493.62 (8)C19—C18—H18119.5
N3—Mn—N472.87 (8)C23—C19—C20117.8 (3)
Mn—O1—H2114.8C23—C19—C18119.2 (3)
Mn—O1—H1131.0C20—C19—C18123.0 (3)
H2—O1—H1109.0C21—C20—C19119.1 (3)
H1A—O1W—H1B118.4C21—C20—H20120.4
C31—O31—Mn131.87 (18)C19—C20—H20120.4
C35—O33—H33102.0C20—C21—C22119.6 (3)
C45—O43—H43101.1C20—C21—H21120.2
C1—N1—C12118.6 (3)C22—C21—H21120.2
C1—N1—Mn126.8 (2)N4—C22—C21123.3 (3)
C12—N1—Mn114.37 (18)N4—C22—H22118.3
C10—N2—C11117.4 (2)C21—C22—H22118.3
C10—N2—Mn127.05 (19)N4—C23—C19122.7 (2)
C11—N2—Mn115.53 (19)N4—C23—C24117.1 (2)
C13—N3—C24117.5 (2)C19—C23—C24120.2 (2)
C13—N3—Mn126.57 (19)N3—C24—C16123.1 (2)
C24—N3—Mn115.72 (16)N3—C24—C23117.9 (2)
C22—N4—C23117.4 (2)C16—C24—C23119.0 (2)
C22—N4—Mn126.88 (19)O32—C31—O31124.3 (3)
C23—N4—Mn115.37 (16)O32—C31—C32119.0 (2)
N1—C1—C2122.5 (3)O31—C31—C32116.7 (2)
N1—C1—H4118.8C33—C32—C37117.9 (2)
C2—C1—H4118.8C33—C32—C31121.7 (2)
C3—C2—C1119.0 (3)C37—C32—C31120.3 (2)
C3—C2—H7120.5C34—C33—C32121.2 (2)
C1—C2—H7120.5C34—C33—H32119.4
C2—C3—C4120.6 (3)C32—C33—H32119.4
C2—C3—H3119.7C33—C34—C35119.9 (3)
C4—C3—H3119.7C33—C34—H34120.0
C3—C4—C12117.1 (3)C35—C34—H34120.0
C3—C4—C5124.0 (3)O33—C35—C34118.0 (2)
C12—C4—C5118.9 (3)O33—C35—C36122.4 (2)
C6—C5—C4121.5 (3)C34—C35—C36119.6 (3)
C6—C5—H5119.2C37—C36—C35119.7 (2)
C4—C5—H5119.2C37—C36—H36120.2
C5—C6—C7121.8 (3)C35—C36—H36120.2
C5—C6—H6119.1C36—C37—C32121.7 (2)
C7—C6—H6119.1C36—C37—H37119.2
C8—C7—C11116.8 (3)C32—C37—H37119.2
C8—C7—C6124.5 (3)O41—C41—O42125.6 (3)
C11—C7—C6118.6 (3)O41—C41—C42117.2 (3)
C9—C8—C7120.4 (3)O42—C41—C42117.2 (3)
C9—C8—H8119.8C47—C42—C43117.8 (3)
C7—C8—H8119.8C47—C42—C41121.3 (3)
C8—C9—C10118.7 (3)C43—C42—C41120.8 (3)
C8—C9—H9120.7C44—C43—C42121.0 (3)
C10—C9—H9120.7C44—C43—H42119.5
N2—C10—C9124.1 (3)C42—C43—H42119.5
N2—C10—H10118.0C45—C44—C43120.1 (3)
C9—C10—H10118.0C45—C44—H44120.0
N2—C11—C7122.6 (3)C43—C44—H44120.0
N2—C11—C12117.9 (3)C44—C45—O43123.4 (3)
C7—C11—C12119.5 (3)C44—C45—C46120.1 (3)
N1—C12—C4122.2 (3)O43—C45—C46116.5 (3)
N1—C12—C11118.3 (2)C47—C46—C45119.3 (3)
C4—C12—C11119.5 (3)C47—C46—H46120.4
N3—C13—C14123.5 (3)C45—C46—H46120.4
N3—C13—H13118.3C46—C47—C42121.7 (3)
C14—C13—H13118.3C46—C47—H47119.1
C15—C14—C13119.0 (3)C42—C47—H47119.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1W0.921.752.661 (3)171
O1W—H1A···O420.931.882.808 (3)174
O1W—H1B···O33i0.982.093.069 (3)174
O33—H33···O41ii0.911.682.565 (3)163
O43—H43···O42iii0.961.832.636 (3)139
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x, y+1, z; (iii) x+1, y, z.
 

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