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The title compound, [Mn(C8H7O3)2(C12H8N2)(H2O)]·C8H8O3, has been synthesized by the reaction of MnCl2·6H2O with p-anisic acid and 1,10-phenanthroline in an alcohol-water solution. The Mn atom is six-coordinated by two N atoms and four O atoms, forming a distorted octahedral geometry. The Mn-O and Mn-N distances range from 2.113 (3) to 2.410 (3) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804003332/hb6012sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804003332/hb6012Isup2.hkl
Contains datablock I

CCDC reference: 239073

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.051
  • wR factor = 0.127
  • Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) ..... 10 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Bruker, 1997); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(I) top
Crystal data top
[Mn(C8H7O3)2(C12H8N2)(H2O)]·C8H8O3Z = 2
Mr = 707.58F(000) = 734
Triclinic, P1Dx = 1.431 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.7353 (6) ÅCell parameters from 5737 reflections
b = 11.3832 (2) Åθ = 2.0–25.0°
c = 16.0107 (1) ŵ = 0.47 mm1
α = 76.41 (3)°T = 293 K
β = 71.56 (2)°Block, yellow
γ = 62.855 (18)°0.55 × 0.40 × 0.30 mm
V = 1642.1 (3) Å3
Data collection top
Bruker P4
diffractometer
5737 independent reflections
Radiation source: fine-focus sealed tube4803 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 1212
Tmin = 0.784, Tmax = 0.873k = 1313
10120 measured reflectionsl = 1917
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)] = 0.051Hydrogen site location: difmap (O-H) and geom (C-H)
wR(F2) = 0.127H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.062P)2 + 0.3137P]
where P = (Fo2 + 2Fc2)/3
5737 reflections(Δ/σ)max = 0.001
454 parametersΔρmax = 0.26 e Å3
3 restraintsΔρmin = 0.24 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
Mn10.71785 (4)0.70129 (4)0.04640 (3)0.03842 (15)
O40.8607 (2)0.63663 (19)0.09218 (12)0.0437 (5)
O10.63402 (19)0.83245 (19)0.14444 (12)0.0445 (5)
O50.7590 (2)0.8435 (2)0.06416 (13)0.0530 (5)
N10.4967 (2)0.7554 (2)0.02952 (14)0.0372 (5)
N20.6662 (2)0.5248 (2)0.10672 (14)0.0376 (5)
O20.8265 (2)0.8081 (2)0.18201 (15)0.0565 (6)
O80.0347 (2)0.7649 (2)0.25235 (16)0.0596 (6)
O100.9168 (3)0.6086 (3)0.08843 (19)0.0686 (7)
O30.3358 (2)1.1922 (2)0.46013 (14)0.0604 (6)
C150.8412 (3)0.7564 (3)0.11611 (18)0.0395 (6)
C100.9197 (3)0.9200 (3)0.22488 (18)0.0435 (7)
H10A0.86990.97970.18240.052*
O61.1421 (2)0.9133 (2)0.44633 (13)0.0608 (6)
C270.5345 (3)0.5384 (3)0.10566 (16)0.0344 (6)
C10.5968 (3)0.9541 (3)0.25725 (17)0.0383 (6)
C230.4837 (3)0.4388 (3)0.14346 (17)0.0398 (6)
C70.6927 (3)0.8594 (3)0.19007 (18)0.0386 (6)
O90.6035 (2)0.5201 (2)0.38519 (15)0.0629 (6)
C90.9174 (3)0.7956 (3)0.20565 (17)0.0365 (6)
C200.3081 (3)0.6791 (3)0.06150 (17)0.0392 (6)
C280.4447 (3)0.6607 (3)0.06415 (16)0.0338 (6)
C110.9946 (3)0.9565 (3)0.30603 (19)0.0482 (7)
H11A0.99551.04010.31800.058*
C131.0651 (3)0.7453 (3)0.35232 (18)0.0455 (7)
H13A1.11310.68670.39540.055*
C121.0684 (3)0.8687 (3)0.36949 (18)0.0441 (7)
C290.2203 (3)0.6216 (3)0.32161 (18)0.0439 (7)
C140.9896 (3)0.7097 (3)0.27023 (18)0.0423 (6)
H14A0.98770.62640.25850.051*
C20.6527 (3)0.9853 (3)0.3126 (2)0.0478 (7)
H2A0.75210.95130.30450.057*
C30.5632 (3)1.0654 (3)0.3786 (2)0.0516 (8)
H3A0.60241.08500.41480.062*
C60.4493 (3)1.0103 (3)0.26903 (19)0.0463 (7)
H6A0.41010.99370.23140.056*
O70.0246 (3)0.5748 (3)0.32377 (18)0.0762 (7)
C190.2226 (3)0.8018 (3)0.0236 (2)0.0527 (8)
H19A0.13040.81840.02120.063*
C220.3455 (3)0.4604 (3)0.13778 (18)0.0464 (7)
H22A0.31220.39430.16170.056*
C210.2622 (3)0.5744 (3)0.09850 (19)0.0478 (7)
H21A0.17240.58560.09530.057*
C260.7479 (3)0.4127 (3)0.1462 (2)0.0510 (8)
H26A0.83880.40180.14710.061*
C300.2958 (3)0.7003 (3)0.28445 (18)0.0412 (6)
H30A0.25860.77560.24620.049*
C40.4155 (3)1.1169 (3)0.39148 (18)0.0462 (7)
C240.5734 (4)0.3233 (3)0.1852 (2)0.0529 (8)
H24A0.54340.25560.21190.064*
C310.4252 (3)0.6691 (3)0.30308 (18)0.0412 (6)
H31A0.47540.72210.27690.049*
C180.2738 (3)0.8971 (3)0.0099 (2)0.0559 (8)
H18A0.21710.97950.03470.067*
C50.3581 (3)1.0909 (3)0.33537 (19)0.0482 (7)
H5A0.25871.12750.34230.058*
C350.0846 (3)0.6497 (3)0.3003 (2)0.0523 (8)
C340.2783 (4)0.5102 (3)0.3779 (2)0.0587 (9)
H34A0.22960.45570.40280.070*
C170.4129 (3)0.8688 (3)0.00630 (19)0.0479 (7)
H17A0.44810.93360.03050.057*
C320.4790 (3)0.5589 (3)0.36087 (19)0.0461 (7)
C250.7051 (4)0.3102 (3)0.1867 (2)0.0596 (9)
H25A0.76590.23370.21440.071*
C360.6792 (4)0.6032 (4)0.3526 (3)0.0677 (10)
H36A0.76440.56530.37480.102*
H36B0.61820.68980.37200.102*
H36C0.70620.61060.28910.102*
C330.4055 (4)0.4781 (3)0.3977 (2)0.0599 (9)
H33A0.44270.40250.43570.072*
C161.2215 (4)0.8271 (4)0.5141 (2)0.0788 (11)
H16A1.26800.87040.56430.118*
H16B1.15710.80560.53140.118*
H16C1.29300.74710.49240.118*
C80.1847 (4)1.2280 (4)0.4854 (3)0.0795 (12)
H8A0.14151.28000.53450.119*
H8B0.16731.14910.50240.119*
H8C0.14321.27890.43640.119*
H8D0.037 (3)0.776 (4)0.235 (3)0.110 (16)*
H10B0.906 (5)0.659 (4)0.123 (2)0.104 (16)*
H10C0.981 (3)0.533 (2)0.099 (2)0.078 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0295 (2)0.0396 (3)0.0488 (3)0.01670 (19)0.00679 (17)0.00818 (18)
O40.0401 (11)0.0364 (12)0.0556 (12)0.0190 (9)0.0061 (9)0.0073 (9)
O10.0361 (10)0.0480 (12)0.0536 (12)0.0134 (9)0.0162 (9)0.0141 (9)
O50.0501 (12)0.0399 (12)0.0560 (12)0.0163 (10)0.0069 (10)0.0143 (10)
N10.0314 (12)0.0383 (13)0.0434 (12)0.0147 (11)0.0083 (9)0.0072 (10)
N20.0322 (12)0.0387 (13)0.0442 (13)0.0149 (11)0.0108 (10)0.0062 (10)
O20.0351 (11)0.0628 (15)0.0764 (15)0.0111 (11)0.0186 (10)0.0288 (11)
O80.0432 (13)0.0551 (15)0.0885 (17)0.0136 (11)0.0244 (12)0.0241 (13)
O100.0401 (13)0.0592 (17)0.112 (2)0.0002 (12)0.0346 (13)0.0406 (16)
O30.0665 (15)0.0528 (14)0.0516 (13)0.0179 (12)0.0027 (11)0.0174 (10)
C150.0286 (14)0.0387 (17)0.0525 (17)0.0138 (13)0.0091 (12)0.0085 (13)
C100.0428 (16)0.0348 (16)0.0493 (16)0.0136 (13)0.0028 (13)0.0147 (13)
O60.0745 (16)0.0532 (14)0.0468 (12)0.0308 (12)0.0049 (11)0.0089 (10)
C270.0326 (14)0.0410 (16)0.0326 (13)0.0168 (12)0.0040 (10)0.0113 (11)
C10.0403 (15)0.0328 (15)0.0428 (15)0.0154 (13)0.0128 (12)0.0013 (11)
C230.0422 (16)0.0456 (17)0.0374 (14)0.0240 (14)0.0032 (12)0.0110 (12)
C70.0379 (16)0.0351 (16)0.0453 (15)0.0165 (13)0.0149 (12)0.0010 (12)
O90.0555 (14)0.0592 (15)0.0805 (16)0.0277 (12)0.0339 (12)0.0133 (12)
C90.0286 (14)0.0341 (15)0.0439 (15)0.0095 (12)0.0079 (11)0.0078 (12)
C200.0308 (14)0.0496 (18)0.0412 (15)0.0163 (13)0.0063 (11)0.0158 (12)
C280.0286 (13)0.0414 (16)0.0337 (13)0.0155 (12)0.0026 (10)0.0129 (11)
C110.0561 (19)0.0367 (17)0.0506 (17)0.0216 (15)0.0064 (14)0.0068 (13)
C130.0482 (17)0.0383 (17)0.0450 (16)0.0123 (14)0.0077 (13)0.0121 (13)
C120.0417 (16)0.0408 (17)0.0424 (15)0.0137 (14)0.0054 (12)0.0048 (13)
C290.0387 (15)0.0465 (18)0.0486 (17)0.0184 (14)0.0042 (12)0.0160 (14)
C140.0411 (16)0.0346 (16)0.0515 (17)0.0148 (13)0.0118 (13)0.0059 (13)
C20.0423 (16)0.0453 (18)0.0583 (18)0.0150 (14)0.0189 (14)0.0076 (14)
C30.058 (2)0.0500 (19)0.0513 (18)0.0182 (16)0.0238 (15)0.0080 (15)
C60.0423 (17)0.0495 (19)0.0520 (17)0.0188 (15)0.0149 (13)0.0099 (14)
O70.0611 (16)0.0847 (19)0.1025 (19)0.0478 (15)0.0169 (14)0.0117 (15)
C190.0329 (16)0.061 (2)0.064 (2)0.0129 (16)0.0175 (14)0.0142 (16)
C220.0471 (17)0.057 (2)0.0464 (16)0.0349 (16)0.0007 (13)0.0130 (14)
C210.0353 (15)0.065 (2)0.0535 (17)0.0285 (16)0.0020 (13)0.0214 (15)
C260.0429 (17)0.0473 (19)0.0651 (19)0.0177 (15)0.0232 (15)0.0021 (15)
C300.0394 (15)0.0383 (16)0.0436 (15)0.0130 (13)0.0074 (12)0.0104 (12)
C40.0586 (19)0.0347 (17)0.0412 (16)0.0181 (15)0.0084 (14)0.0045 (12)
C240.064 (2)0.0471 (19)0.0520 (18)0.0312 (17)0.0115 (15)0.0006 (14)
C310.0398 (15)0.0414 (17)0.0432 (15)0.0194 (13)0.0068 (12)0.0049 (12)
C180.0421 (17)0.049 (2)0.071 (2)0.0087 (15)0.0246 (15)0.0021 (16)
C50.0376 (16)0.0462 (18)0.0559 (18)0.0126 (14)0.0075 (13)0.0120 (14)
C350.0423 (17)0.056 (2)0.0618 (19)0.0198 (16)0.0031 (14)0.0274 (16)
C340.058 (2)0.059 (2)0.069 (2)0.0368 (18)0.0150 (17)0.0023 (17)
C170.0452 (17)0.0398 (18)0.0573 (18)0.0160 (15)0.0141 (14)0.0039 (14)
C320.0413 (16)0.0464 (18)0.0516 (17)0.0177 (14)0.0121 (13)0.0070 (14)
C250.060 (2)0.046 (2)0.070 (2)0.0201 (17)0.0276 (17)0.0116 (16)
C360.051 (2)0.066 (2)0.095 (3)0.0296 (19)0.0319 (19)0.006 (2)
C330.063 (2)0.057 (2)0.065 (2)0.0328 (18)0.0251 (17)0.0132 (16)
C160.100 (3)0.075 (3)0.047 (2)0.040 (2)0.0128 (19)0.0158 (18)
C80.077 (3)0.073 (3)0.075 (2)0.037 (2)0.024 (2)0.030 (2)
Geometric parameters (Å, º) top
Mn1—O12.118 (2)C13—H13A0.9300
Mn1—O102.156 (2)C29—C341.380 (4)
Mn1—O52.181 (2)C29—C301.385 (4)
Mn1—N22.246 (2)C29—C351.476 (4)
Mn1—N12.254 (2)C14—H14A0.9300
Mn1—O42.324 (2)C2—C31.372 (4)
Mn1—C152.594 (3)C2—H2A0.9300
O4—C151.262 (3)C3—C41.379 (4)
O1—C71.263 (3)C3—H3A0.9300
O5—C151.256 (3)C6—C51.382 (4)
N1—C171.313 (4)C6—H6A0.9300
N1—C281.362 (3)O7—C351.217 (4)
N2—C261.322 (4)C19—C181.360 (4)
N2—C271.356 (3)C19—H19A0.9300
O2—C71.254 (3)C22—C211.339 (4)
O8—C351.320 (4)C22—H22A0.9300
O8—H8D0.85 (4)C21—H21A0.9300
O10—H10B0.84 (4)C26—C251.392 (4)
O10—H10C0.84 (4)C26—H26A0.9300
O3—C41.361 (3)C30—C311.381 (4)
O3—C81.422 (4)C30—H30A0.9300
C15—C91.488 (4)C4—C51.384 (4)
C10—C111.378 (4)C24—C251.359 (4)
C10—C91.387 (4)C24—H24A0.9300
C10—H10A0.9300C31—C321.377 (4)
O6—C121.362 (3)C31—H31A0.9300
O6—C161.421 (4)C18—C171.394 (4)
C27—C231.407 (4)C18—H18A0.9300
C27—C281.433 (4)C5—H5A0.9300
C1—C61.377 (4)C34—C331.365 (4)
C1—C21.396 (4)C34—H34A0.9300
C1—C71.487 (4)C17—H17A0.9300
C23—C241.394 (4)C32—C331.390 (4)
C23—C221.419 (4)C25—H25A0.9300
O9—C321.357 (3)C36—H36A0.9600
O9—C361.425 (4)C36—H36B0.9600
C9—C141.380 (4)C36—H36C0.9600
C20—C191.395 (4)C33—H33A0.9300
C20—C281.396 (3)C16—H16A0.9600
C20—C211.427 (4)C16—H16B0.9600
C11—C121.380 (4)C16—H16C0.9600
C11—H11A0.9300C8—H8A0.9600
C13—C121.381 (4)C8—H8B0.9600
C13—C141.387 (4)C8—H8C0.9600
O1—Mn1—O1087.97 (9)C9—C14—C13121.1 (3)
O1—Mn1—O595.28 (8)C9—C14—H14A119.5
O10—Mn1—O5102.27 (10)C13—C14—H14A119.5
O1—Mn1—N2108.26 (8)C3—C2—C1121.0 (3)
O10—Mn1—N291.51 (10)C3—C2—H2A119.5
O5—Mn1—N2153.17 (8)C1—C2—H2A119.5
O1—Mn1—N192.49 (8)C2—C3—C4120.4 (3)
O10—Mn1—N1164.48 (10)C2—C3—H3A119.8
O5—Mn1—N193.14 (8)C4—C3—H3A119.8
N2—Mn1—N173.61 (8)C1—C6—C5121.7 (3)
O1—Mn1—O4150.23 (7)C1—C6—H6A119.1
O10—Mn1—O485.83 (9)C5—C6—H6A119.1
O5—Mn1—O457.94 (7)C18—C19—C20120.1 (3)
N2—Mn1—O4100.99 (8)C18—C19—H19A120.0
N1—Mn1—O4101.06 (7)C20—C19—H19A120.0
O1—Mn1—C15122.85 (8)C21—C22—C23121.1 (3)
O10—Mn1—C1593.52 (10)C21—C22—H22A119.5
O5—Mn1—C1528.89 (8)C23—C22—H22A119.5
N2—Mn1—C15128.77 (8)C22—C21—C20121.4 (3)
N1—Mn1—C1599.22 (8)C22—C21—H21A119.3
O4—Mn1—C1529.09 (7)C20—C21—H21A119.3
C15—O4—Mn187.39 (16)N2—C26—C25123.5 (3)
C7—O1—Mn1132.70 (18)N2—C26—H26A118.3
C15—O5—Mn194.10 (17)C25—C26—H26A118.3
C17—N1—C28117.9 (2)C31—C30—C29121.3 (3)
C17—N1—Mn1126.94 (19)C31—C30—H30A119.3
C28—N1—Mn1115.11 (17)C29—C30—H30A119.3
C26—N2—C27117.4 (2)O3—C4—C3116.0 (3)
C26—N2—Mn1126.71 (18)O3—C4—C5124.5 (3)
C27—N2—Mn1115.86 (17)C3—C4—C5119.5 (3)
C35—O8—H8D112 (3)C25—C24—C23119.5 (3)
Mn1—O10—H10B104 (3)C25—C24—H24A120.2
Mn1—O10—H10C141 (3)C23—C24—H24A120.2
H10B—O10—H10C108 (4)C32—C31—C30119.3 (3)
C4—O3—C8117.7 (3)C32—C31—H31A120.3
O5—C15—O4120.4 (3)C30—C31—H31A120.3
O5—C15—C9119.2 (2)C19—C18—C17118.7 (3)
O4—C15—C9120.4 (2)C19—C18—H18A120.7
O5—C15—Mn157.01 (14)C17—C18—H18A120.7
O4—C15—Mn163.52 (15)C6—C5—C4119.6 (3)
C9—C15—Mn1174.06 (18)C6—C5—H5A120.2
C11—C10—C9120.9 (3)C4—C5—H5A120.2
C11—C10—H10A119.6O7—C35—O8123.1 (3)
C9—C10—H10A119.6O7—C35—C29124.0 (3)
C12—O6—C16117.9 (2)O8—C35—C29113.0 (3)
N2—C27—C23122.9 (2)C33—C34—C29121.5 (3)
N2—C27—C28117.5 (2)C33—C34—H34A119.2
C23—C27—C28119.7 (2)C29—C34—H34A119.2
C6—C1—C2117.8 (3)N1—C17—C18123.4 (3)
C6—C1—C7120.9 (2)N1—C17—H17A118.3
C2—C1—C7121.3 (3)C18—C17—H17A118.3
C24—C23—C27117.5 (2)O9—C32—C31124.4 (3)
C24—C23—C22123.4 (3)O9—C32—C33115.6 (3)
C27—C23—C22119.1 (3)C31—C32—C33120.0 (3)
O2—C7—O1122.9 (3)C24—C25—C26119.3 (3)
O2—C7—C1119.4 (2)C24—C25—H25A120.4
O1—C7—C1117.7 (2)C26—C25—H25A120.4
C32—O9—C36117.7 (2)O9—C36—H36A109.5
C14—C9—C10118.6 (2)O9—C36—H36B109.5
C14—C9—C15121.6 (2)H36A—C36—H36B109.5
C10—C9—C15119.9 (2)O9—C36—H36C109.5
C19—C20—C28117.3 (3)H36A—C36—H36C109.5
C19—C20—C21123.5 (3)H36B—C36—H36C109.5
C28—C20—C21119.2 (3)C34—C33—C32119.7 (3)
N1—C28—C20122.6 (2)C34—C33—H33A120.1
N1—C28—C27117.9 (2)C32—C33—H33A120.1
C20—C28—C27119.5 (2)O6—C16—H16A109.5
C10—C11—C12119.9 (3)O6—C16—H16B109.5
C10—C11—H11A120.1H16A—C16—H16B109.5
C12—C11—H11A120.1O6—C16—H16C109.5
C12—C13—C14119.4 (3)H16A—C16—H16C109.5
C12—C13—H13A120.3H16B—C16—H16C109.5
C14—C13—H13A120.3O3—C8—H8A109.5
O6—C12—C11115.1 (3)O3—C8—H8B109.5
O6—C12—C13124.8 (3)H8A—C8—H8B109.5
C11—C12—C13120.1 (3)O3—C8—H8C109.5
C34—C29—C30118.2 (3)H8A—C8—H8C109.5
C34—C29—C35119.3 (3)H8B—C8—H8C109.5
C30—C29—C35122.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O10—H10B···O20.84 (4)1.85 (2)2.649 (3)159 (4)
O10—H10C···O4i0.84 (4)1.91 (2)2.726 (3)165 (4)
O8—H8D···O2ii0.85 (4)1.77 (2)2.615 (3)171 (4)
Symmetry codes: (i) x+2, y+1, z; (ii) x1, y, z.
 

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