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In the title polymeric structure, {[Mn(C8H3NO6)(C12H8N2)]·H2O}n, the Mn atom adopts an octahedral geometry. The 2-nitro­benzene-1,4-di­carboxyl­ate ligand is in a chelating–bridging mode and its two carboxyl­ate groups are approximately perpendicular to each other. The crystal structure can be described as layers formed by a two-dimensional network of hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805009086/ac6166sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805009086/ac6166Isup2.hkl
Contains datablock I

CCDC reference: 270224

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.063
  • wR factor = 0.142
  • Data-to-parameter ratio = 11.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _diffrn_reflns_theta_full 0.00 From the CIF: _reflns_number_total 3197 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3379 Completeness (_total/calc) 94.61% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.95 PLAT128_ALERT_4_C Non-standard setting of Space group C2/c .... I2/a PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C6 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Poly[[[(1,10-phenanthroline)manganese(II)]-µ3-2-nitrobenzene-1,4- dicarboxylato] monohydrate] top
Crystal data top
[Mn(C8H3NO6)(C12H8N2)]·H2OF(000) = 1880
Mr = 462.27Dx = 1.600 Mg m3
Monoclinic, I2/aMo Kα radiation, λ = 0.71073 Å
Hall symbol: -I 2yaCell parameters from 3483 reflections
a = 18.515 (3) Åθ = 2.2–26.6°
b = 9.927 (2) ŵ = 0.74 mm1
c = 20.948 (3) ÅT = 295 K
β = 94.659 (3)°Block, pale yellow
V = 3837 (1) Å30.28 × 0.18 × 0.16 mm
Z = 8
Data collection top
Bruker APEX area-detector
diffractometer
3197 independent reflections
Radiation source: fine-focus sealed tube2021 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 2122
Tmin = 0.820, Tmax = 0.891k = 118
7693 measured reflectionsl = 2422
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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0503P)2]
where P = (Fo2 + 2Fc2)/3
3197 reflections(Δ/σ)max < 0.001
286 parametersΔρmax = 0.35 e Å3
2 restraintsΔρmin = 0.37 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
Mn10.06507 (4)0.03268 (7)0.17918 (3)0.0344 (3)
N10.0256 (2)0.0470 (4)0.10043 (18)0.0382 (10)
N20.1010 (2)0.1839 (4)0.10756 (19)0.0398 (10)
N30.3879 (2)0.3721 (4)0.1436 (2)0.0472 (11)
O10.15756 (16)0.1022 (3)0.14920 (16)0.0443 (9)
O20.17238 (17)0.0249 (3)0.23499 (16)0.0444 (9)
O30.54032 (16)0.1955 (3)0.24027 (16)0.0452 (9)
O40.49302 (16)0.3728 (3)0.28361 (16)0.0462 (9)
O50.4510 (2)0.4035 (4)0.14722 (18)0.0625 (11)
O60.3417 (2)0.4252 (4)0.1072 (2)0.0882 (16)
OW10.1740 (3)0.2421 (5)0.3238 (4)0.136 (3)
C10.0877 (3)0.0207 (5)0.0964 (3)0.0466 (13)
C20.1421 (3)0.0012 (5)0.0481 (3)0.0542 (16)
C30.1337 (3)0.0926 (5)0.0027 (3)0.0496 (14)
C40.0699 (3)0.1687 (5)0.0042 (2)0.0412 (13)
C50.0545 (3)0.2688 (6)0.0421 (3)0.0586 (16)
C60.0091 (4)0.3360 (6)0.0390 (3)0.0700 (19)
C70.0643 (3)0.3109 (5)0.0116 (3)0.0511 (14)
C80.1301 (3)0.3774 (6)0.0179 (3)0.0692 (18)
C90.1794 (3)0.3480 (6)0.0670 (3)0.076 (2)
C100.1635 (3)0.2497 (6)0.1103 (3)0.0593 (16)
C110.0163 (3)0.1403 (4)0.0547 (2)0.0365 (12)
C120.0515 (3)0.2131 (5)0.0581 (2)0.0399 (12)
C130.1957 (2)0.0585 (5)0.1962 (3)0.0354 (12)
C140.2729 (2)0.1069 (4)0.2071 (2)0.0327 (11)
C150.2971 (2)0.2118 (4)0.1718 (2)0.0319 (11)
C160.3653 (2)0.2618 (4)0.1848 (2)0.0305 (11)
C170.4128 (2)0.2116 (4)0.2338 (2)0.0314 (11)
C180.3888 (2)0.1036 (5)0.2675 (2)0.0394 (12)
C190.3206 (2)0.0524 (4)0.2550 (2)0.0372 (12)
C200.4876 (2)0.2665 (5)0.2524 (2)0.0360 (12)
H10.09490.08460.12770.056*
H20.18420.05250.04690.065*
H30.17040.10680.02970.060*
H50.08940.28810.07530.070*
H60.01720.39960.07030.084*
H80.14050.44260.01190.083*
H90.22340.39340.07150.092*
H100.19840.22850.14310.071*
H150.26680.24890.13880.038*
H180.41970.06460.29960.047*
H190.30590.02020.27880.045*
H2W10.167 (4)0.163 (3)0.337 (3)0.080*
H1W10.1348 (18)0.255 (6)0.300 (2)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0261 (4)0.0347 (4)0.0413 (5)0.0035 (3)0.0046 (3)0.0036 (3)
N10.037 (2)0.041 (3)0.035 (2)0.0000 (19)0.005 (2)0.0049 (19)
N20.030 (2)0.042 (2)0.047 (3)0.0007 (19)0.002 (2)0.009 (2)
N30.044 (3)0.044 (3)0.053 (3)0.001 (2)0.004 (2)0.001 (2)
O10.0282 (19)0.057 (2)0.046 (2)0.0020 (16)0.0097 (17)0.0025 (18)
O20.033 (2)0.048 (2)0.051 (2)0.0090 (16)0.0011 (18)0.0046 (18)
O30.0242 (18)0.044 (2)0.065 (2)0.0047 (16)0.0077 (18)0.0132 (18)
O40.035 (2)0.037 (2)0.065 (2)0.0031 (15)0.0071 (18)0.0265 (18)
O50.045 (2)0.069 (3)0.074 (3)0.021 (2)0.006 (2)0.020 (2)
O60.071 (3)0.096 (4)0.092 (3)0.012 (3)0.025 (3)0.053 (3)
OW10.081 (4)0.106 (4)0.209 (7)0.027 (4)0.065 (4)0.072 (5)
C10.043 (3)0.051 (3)0.045 (3)0.005 (3)0.001 (3)0.002 (3)
C20.046 (4)0.059 (4)0.056 (4)0.000 (3)0.007 (3)0.010 (3)
C30.042 (3)0.059 (4)0.046 (3)0.009 (3)0.012 (3)0.009 (3)
C40.038 (3)0.043 (3)0.041 (3)0.004 (2)0.002 (3)0.002 (2)
C50.072 (4)0.055 (4)0.046 (4)0.013 (3)0.009 (3)0.006 (3)
C60.095 (5)0.054 (4)0.058 (4)0.004 (4)0.012 (4)0.019 (3)
C70.058 (4)0.049 (3)0.046 (3)0.002 (3)0.004 (3)0.006 (3)
C80.075 (5)0.063 (4)0.070 (5)0.005 (3)0.008 (4)0.020 (3)
C90.060 (4)0.083 (5)0.084 (5)0.019 (4)0.005 (4)0.024 (4)
C100.042 (3)0.068 (4)0.067 (4)0.007 (3)0.002 (3)0.020 (3)
C110.040 (3)0.031 (3)0.039 (3)0.001 (2)0.001 (2)0.001 (2)
C120.046 (3)0.035 (3)0.039 (3)0.004 (2)0.007 (3)0.004 (2)
C130.025 (3)0.033 (3)0.049 (3)0.006 (2)0.004 (2)0.008 (2)
C140.028 (3)0.032 (3)0.037 (3)0.004 (2)0.002 (2)0.000 (2)
C150.026 (3)0.036 (3)0.032 (3)0.001 (2)0.009 (2)0.000 (2)
C160.027 (3)0.030 (3)0.035 (3)0.002 (2)0.004 (2)0.002 (2)
C170.027 (2)0.026 (3)0.041 (3)0.008 (2)0.002 (2)0.005 (2)
C180.027 (3)0.038 (3)0.050 (3)0.004 (2)0.014 (2)0.002 (2)
C190.031 (3)0.032 (3)0.049 (3)0.002 (2)0.001 (2)0.007 (2)
C200.021 (3)0.042 (3)0.044 (3)0.006 (2)0.007 (2)0.007 (3)
Geometric parameters (Å, º) top
Mn1—O12.301 (3)C7—C81.381 (7)
Mn1—O22.223 (3)C7—C121.408 (7)
Mn1—O3i2.134 (3)C8—C91.350 (7)
Mn1—O4ii2.102 (3)C9—C101.380 (7)
Mn1—N12.260 (4)C11—C121.444 (6)
Mn1—N22.260 (4)C13—C141.507 (6)
N1—C11.328 (6)C14—C151.373 (6)
N1—C111.354 (6)C14—C191.391 (6)
N2—C101.325 (6)C15—C161.365 (6)
N2—C121.359 (5)C16—C171.389 (6)
N3—O51.205 (5)C17—C181.378 (6)
N3—O61.218 (5)C17—C201.509 (6)
N3—C161.476 (6)C18—C191.367 (6)
O1—C131.243 (5)C1—H10.9300
O2—C131.260 (5)C2—H20.9300
O3—C201.246 (5)C3—H30.9300
O3—Mn1iii2.134 (3)C5—H50.9300
O4—C201.241 (5)C6—H60.9300
O4—Mn1ii2.102 (3)C8—H80.9300
C1—C21.383 (6)C9—H90.9300
C2—C31.350 (7)C10—H100.9300
C3—C41.401 (7)C15—H150.9300
C4—C111.419 (6)C18—H180.9300
C4—C51.433 (7)C19—H190.9300
C5—C61.350 (8)OW1—H2W10.85 (4)
C6—C71.435 (7)OW1—H1W10.86 (4)
O4ii—Mn1—O3i102.0 (1)N2—C12—C11117.4 (4)
O4ii—Mn1—O2104.0 (1)C7—C12—C11120.4 (5)
O3i—Mn1—O286.4 (1)O1—C13—O2122.5 (4)
O4ii—Mn1—N2159.2 (1)O1—C13—C14118.7 (4)
O3i—Mn1—N289.1 (1)O2—C13—C14118.9 (4)
O2—Mn1—N294.2 (1)O1—C13—Mn163.0 (2)
O4ii—Mn1—N186.9 (1)O2—C13—Mn159.5 (2)
O3i—Mn1—N1102.0 (1)C14—C13—Mn1178.0 (4)
O2—Mn1—N1164.8 (1)C15—C14—C19117.9 (4)
N2—Mn1—N173.4 (1)C15—C14—C13120.4 (4)
O4ii—Mn1—O194.4 (1)C19—C14—C13121.6 (4)
O3i—Mn1—O1143.6 (1)C16—C15—C14120.4 (4)
O2—Mn1—O158.0 (1)C15—C16—C17122.5 (4)
N2—Mn1—O186.5 (1)C15—C16—N3117.0 (4)
N1—Mn1—O1111.3 (1)C17—C16—N3120.4 (4)
C1—N1—C11117.4 (4)C18—C17—C16116.6 (4)
C1—N1—Mn1127.0 (3)C18—C17—C20118.4 (4)
C11—N1—Mn1115.5 (3)C16—C17—C20125.0 (4)
C10—N2—C12117.4 (4)C19—C18—C17121.5 (4)
C10—N2—Mn1127.0 (3)C18—C19—C14121.1 (4)
C12—N2—Mn1115.6 (3)O4—C20—O3123.9 (4)
O5—N3—O6123.7 (5)O4—C20—C17118.4 (4)
O5—N3—C16118.3 (4)O3—C20—C17117.4 (4)
O6—N3—C16118.0 (4)H2W1—OW1—H1W1100 (6)
C13—O1—Mn188.2 (3)N1—C1—H1118.3
C13—O2—Mn191.3 (3)C2—C1—H1118.3
C20—O3—Mn1iii139.5 (3)C3—C2—H2120.2
C20—O4—Mn1ii144.6 (3)C1—C2—H2120.2
N1—C1—C2123.5 (5)C2—C3—H3120.0
C3—C2—C1119.6 (5)C4—C3—H3120.0
C2—C3—C4120.1 (5)C6—C5—H5119.0
C3—C4—C11116.6 (5)C4—C5—H5119.0
C3—C4—C5124.9 (5)C5—C6—H6119.5
C11—C4—C5118.4 (5)C7—C6—H6119.5
C6—C5—C4122.1 (5)C9—C8—H8119.8
C5—C6—C7121.1 (6)C7—C8—H8119.8
C8—C7—C12117.5 (5)C8—C9—H9120.4
C8—C7—C6123.9 (5)C10—C9—H9120.4
C12—C7—C6118.7 (5)N2—C10—H10118.2
C9—C8—C7120.3 (6)C9—C10—H10118.2
C8—C9—C10119.1 (6)C16—C15—H15119.8
N2—C10—C9123.5 (5)C14—C15—H15119.8
N1—C11—C4122.8 (4)C19—C18—H18119.3
N1—C11—C12117.9 (4)C17—C18—H18119.3
C4—C11—C12119.3 (4)C18—C19—H19119.4
N2—C12—C7122.2 (5)C14—C19—H19119.4
O4ii—Mn1—N1—C16.5 (4)C3—C4—C11—C12178.6 (4)
O3i—Mn1—N1—C195.1 (4)C5—C4—C11—C120.4 (7)
O2—Mn1—N1—C1142.6 (5)C10—N2—C12—C71.2 (7)
N2—Mn1—N1—C1179.4 (4)Mn1—N2—C12—C7176.4 (4)
O1—Mn1—N1—C1100.0 (4)C10—N2—C12—C11179.3 (5)
C13—Mn1—N1—C1109.3 (4)Mn1—N2—C12—C113.2 (5)
O4ii—Mn1—N1—C11177.3 (3)C8—C7—C12—N20.1 (8)
O3i—Mn1—N1—C1181.1 (3)C6—C7—C12—N2179.8 (5)
O2—Mn1—N1—C1141.1 (7)C8—C7—C12—C11179.7 (5)
N2—Mn1—N1—C114.3 (3)C6—C7—C12—C110.3 (8)
O1—Mn1—N1—C1183.8 (3)N1—C11—C12—N20.7 (7)
C13—Mn1—N1—C1174.4 (4)C4—C11—C12—N2179.3 (4)
O4ii—Mn1—N2—C10158.6 (4)N1—C11—C12—C7179.7 (4)
O3i—Mn1—N2—C1078.4 (5)C4—C11—C12—C70.3 (7)
O2—Mn1—N2—C107.9 (5)Mn1—O1—C13—O21.1 (5)
N1—Mn1—N2—C10178.8 (5)Mn1—O1—C13—C14178.7 (4)
O1—Mn1—N2—C1065.4 (5)Mn1—O2—C13—O11.1 (5)
C13—Mn1—N2—C1036.8 (5)Mn1—O2—C13—C14178.7 (4)
O4ii—Mn1—N2—C1224.1 (6)O4ii—Mn1—C13—O179.5 (3)
O3i—Mn1—N2—C1298.8 (3)O3i—Mn1—C13—O1171.6 (2)
O2—Mn1—N2—C12174.9 (3)O2—Mn1—C13—O1178.9 (5)
N1—Mn1—N2—C123.9 (3)N2—Mn1—C13—O182.6 (3)
O1—Mn1—N2—C12117.3 (3)N1—Mn1—C13—O118.3 (4)
C13—Mn1—N2—C12145.9 (3)O4ii—Mn1—C13—O299.5 (3)
O4ii—Mn1—O1—C13104.3 (3)O3i—Mn1—C13—O29.4 (3)
O3i—Mn1—O1—C1312.8 (4)N2—Mn1—C13—O298.5 (3)
O2—Mn1—O1—C130.6 (3)N1—Mn1—C13—O2162.8 (3)
N2—Mn1—O1—C1396.5 (3)O1—Mn1—C13—O2178.9 (5)
N1—Mn1—O1—C13167.3 (3)O1—C13—C14—C159.8 (7)
O4ii—Mn1—O2—C1387.0 (3)O2—C13—C14—C15170.4 (4)
O3i—Mn1—O2—C13171.5 (3)O1—C13—C14—C19173.5 (4)
N2—Mn1—O2—C1382.6 (3)O2—C13—C14—C196.3 (7)
N1—Mn1—O2—C1347.5 (6)C19—C14—C15—C161.5 (7)
O1—Mn1—O2—C130.6 (3)C13—C14—C15—C16175.3 (4)
C11—N1—C1—C20.5 (7)C14—C15—C16—C170.7 (7)
Mn1—N1—C1—C2176.7 (4)C14—C15—C16—N3178.4 (4)
N1—C1—C2—C31.3 (8)O5—N3—C16—C15168.4 (4)
C1—C2—C3—C40.7 (8)O6—N3—C16—C1510.7 (7)
C2—C3—C4—C110.6 (8)O5—N3—C16—C1710.7 (7)
C2—C3—C4—C5178.7 (5)O6—N3—C16—C17170.2 (5)
C3—C4—C5—C6178.0 (6)C15—C16—C17—C182.7 (7)
C11—C4—C5—C60.1 (8)N3—C16—C17—C18176.3 (4)
C4—C5—C6—C70.7 (10)C15—C16—C17—C20177.2 (4)
C5—C6—C7—C8179.2 (6)N3—C16—C17—C203.8 (7)
C5—C6—C7—C120.7 (9)C16—C17—C18—C192.6 (7)
C12—C7—C8—C90.0 (9)C20—C17—C18—C19177.3 (4)
C6—C7—C8—C9180.0 (6)C17—C18—C19—C140.5 (8)
C7—C8—C9—C100.8 (10)C15—C14—C19—C181.6 (7)
C12—N2—C10—C92.1 (9)C13—C14—C19—C18175.2 (4)
Mn1—N2—C10—C9175.1 (5)Mn1ii—O4—C20—O3179.6 (3)
C8—C9—C10—N22.0 (10)Mn1ii—O4—C20—C176.3 (8)
C1—N1—C11—C40.9 (7)Mn1iii—O3—C20—O4166.3 (3)
Mn1—N1—C11—C4175.7 (3)Mn1iii—O3—C20—C1720.4 (7)
C1—N1—C11—C12179.1 (4)C18—C17—C20—O4103.5 (5)
Mn1—N1—C11—C124.3 (6)C16—C17—C20—O476.4 (6)
C3—C4—C11—N11.4 (7)C18—C17—C20—O370.2 (6)
C5—C4—C11—N1179.6 (5)C16—C17—C20—O3109.9 (5)
Symmetry codes: (i) x1/2, y, z; (ii) x+1/2, y1/2, z+1/2; (iii) x+1/2, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
OW1—H1W1···O3i0.86 (4)2.15 (3)2.949 (6)156 (5)
Symmetry code: (i) x1/2, y, z.
 

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