catena-Poly[[aqua­(2,2′-bipyridine)manganese(II)]-μ₂-5-nitro­benzene-1,3-dicarboxyl­ato-κ³O:O′,O′′]

In the title compound, [Mn(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)]_n, the coordination polyhedron of the Mn^II ion is an octa­hedron defined by an N₂O₄ donor set. Each pair of adjacent Mn^II ions is bridged by a 5-nitro­benzene-1,3-dicarboxyl­ate dianion to form a chiral helical chain running along a crystallographic 2₁ axis in the c direction with a long pitch of 19.04 Å. These chains are linked by O_water—H...O hydrogen bonds into a layer structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.045
• wR factor = 0.113
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.60
           From the CIF: _reflns_number_total               3923
           Count of symmetry unique reflns         2383
           Completeness (_total/calc)            164.62%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1540
           Fraction of Friedel pairs measured     0.646
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 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

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Computing details

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: SHELXTL (Bruker, 2005); software used to prepare material for publication: SHELXTL.

catena-Poly[[aqua(2,2'-bipyridine)manganese(II)]-µ₂-5-nitrobenzene- 1,3-dicarboxylato-κ³O:O',O'']

Crystal data

[Mn(C8H3NO6)(C10H8N2)(H2O)]	F(000) = 892
Mr = 438.25	Dx = 1.649 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 976 reflections
a = 5.2027 (2) Å	θ = 2.4–23.5°
b = 17.8203 (7) Å	µ = 0.80 mm^−1
c = 19.0427 (7) Å	T = 293 K
V = 1765.52 (12) Å^3	Lath, colorless
Z = 4	0.33 × 0.13 × 0.07 mm

Data collection

Bruker APEX area-detector diffractometer	3923 independent reflections
Radiation source: fine-focus sealed tube	2866 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
φ and ω scans	θmax = 27.6°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.779, Tmax = 0.950	k = −21→23
9400 measured reflections	l = −24→21

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2)]
S = 1.00	(Δ/σ)max = 0.001
3923 reflections	Δρmax = 0.27 e Å^−3
268 parameters	Δρmin = −0.34 e Å^−3
4 restraints	Absolute structure: Flack (1983), 1540 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Mn1	0.65315 (11)	0.87839 (3)	0.79999 (3)	0.02759 (16)
C1	1.0842 (8)	0.8060 (2)	0.9000 (2)	0.0367 (9)
H1	1.1224	0.8562	0.9087	0.044*
C2	1.2291 (8)	0.7523 (2)	0.9332 (2)	0.0419 (10)
H2	1.3609	0.7657	0.9637	0.050*
C3	1.1749 (10)	0.6784 (2)	0.9204 (2)	0.0496 (11)
H3	1.2714	0.6406	0.9414	0.060*
C4	0.9719 (10)	0.6605 (2)	0.8752 (2)	0.0474 (11)
H4	0.9272	0.6107	0.8670	0.057*
C5	0.8392 (9)	0.71798 (19)	0.84274 (18)	0.0334 (8)
C6	0.6216 (8)	0.70463 (19)	0.79152 (19)	0.0348 (9)
C7	0.5628 (10)	0.6341 (2)	0.7658 (3)	0.0517 (12)
H7	0.6536	0.5925	0.7816	0.062*
C8	0.3771 (11)	0.6255 (3)	0.7185 (3)	0.0603 (13)
H8	0.3414	0.5784	0.7000	0.072*
C9	0.2364 (10)	0.6879 (2)	0.6969 (2)	0.0515 (12)
H9	0.1005	0.6833	0.6654	0.062*
C10	0.3067 (9)	0.7567 (2)	0.7240 (2)	0.0397 (10)
H10	0.2185	0.7992	0.7089	0.048*
C11	0.7500 (8)	0.92867 (19)	0.58250 (18)	0.0275 (8)
C12	0.8184 (8)	0.97779 (19)	0.52924 (17)	0.0282 (8)
H12	0.9541	1.0109	0.5363	0.034*
C13	0.6899 (8)	0.97862 (19)	0.46629 (17)	0.0274 (8)
C14	0.4857 (8)	0.92859 (19)	0.4546 (2)	0.0305 (8)
H14	0.3951	0.9290	0.4126	0.037*
C15	0.4235 (7)	0.8787 (2)	0.50758 (18)	0.0305 (8)
C16	0.5519 (7)	0.8786 (2)	0.57181 (18)	0.0325 (8)
H16	0.5045	0.8452	0.6070	0.039*
C17	0.8895 (8)	0.9299 (2)	0.65231 (18)	0.0329 (9)
C18	0.7597 (8)	1.03297 (19)	0.40949 (18)	0.0280 (8)
N1	0.4946 (6)	0.76523 (16)	0.77056 (16)	0.0295 (7)
N2	0.8917 (7)	0.79046 (16)	0.85613 (15)	0.0315 (8)
N3	0.2188 (7)	0.82460 (18)	0.49580 (19)	0.0388 (8)
O1	0.8012 (5)	0.88749 (14)	0.69924 (13)	0.0422 (7)
O2	1.0807 (6)	0.97100 (16)	0.65854 (14)	0.0461 (8)
O3	0.9422 (6)	1.07735 (15)	0.41780 (14)	0.0415 (7)
O4	0.6265 (6)	1.03312 (13)	0.35298 (11)	0.0327 (6)
O5	0.1395 (8)	0.81766 (19)	0.43551 (19)	0.0703 (10)
O6	0.1388 (7)	0.78916 (16)	0.54521 (17)	0.0554 (8)
O7	0.3290 (6)	0.94529 (16)	0.77798 (13)	0.0403 (7)
H7A	0.208 (6)	0.953 (2)	0.8085 (14)	0.061*
H7B	0.270 (7)	0.953 (2)	0.7375 (11)	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.0330 (3)	0.0264 (3)	0.0234 (2)	−0.0021 (3)	−0.0022 (3)	0.0005 (2)
C1	0.036 (2)	0.043 (2)	0.0315 (19)	−0.0019 (18)	0.0025 (18)	0.0039 (17)
C2	0.037 (2)	0.055 (3)	0.034 (2)	0.004 (2)	0.0011 (19)	0.0085 (19)
C3	0.047 (3)	0.050 (2)	0.052 (2)	0.010 (2)	−0.002 (2)	0.017 (2)
C4	0.058 (3)	0.029 (2)	0.056 (3)	0.006 (2)	0.002 (3)	0.007 (2)
C5	0.039 (2)	0.0323 (19)	0.0292 (17)	0.001 (2)	0.006 (2)	0.0012 (15)
C6	0.046 (2)	0.0237 (16)	0.0345 (19)	−0.0025 (17)	0.012 (2)	−0.0026 (15)
C7	0.060 (3)	0.033 (2)	0.062 (3)	−0.002 (2)	−0.003 (2)	−0.010 (2)
C8	0.076 (3)	0.039 (2)	0.066 (3)	−0.010 (3)	−0.002 (3)	−0.024 (2)
C9	0.063 (3)	0.054 (3)	0.038 (2)	−0.017 (2)	−0.001 (2)	−0.013 (2)
C10	0.046 (3)	0.043 (2)	0.0303 (18)	−0.006 (2)	0.004 (2)	−0.0033 (16)
C11	0.0327 (19)	0.0254 (17)	0.0244 (17)	0.0018 (15)	−0.0008 (16)	0.0019 (14)
C12	0.028 (2)	0.0284 (17)	0.0278 (17)	−0.0009 (17)	0.0049 (18)	−0.0006 (14)
C13	0.031 (2)	0.0292 (17)	0.0221 (15)	0.0007 (16)	0.0015 (17)	0.0010 (14)
C14	0.035 (2)	0.0292 (18)	0.0279 (19)	−0.0002 (17)	0.0001 (17)	0.0021 (15)
C15	0.034 (2)	0.0260 (17)	0.0316 (17)	−0.0071 (18)	−0.0002 (15)	0.0022 (16)
C16	0.038 (2)	0.0291 (18)	0.0302 (17)	−0.0012 (19)	0.0053 (16)	0.0054 (17)
C17	0.044 (3)	0.0327 (19)	0.0220 (17)	0.0014 (19)	0.0041 (18)	0.0036 (14)
C18	0.032 (2)	0.0277 (18)	0.0240 (17)	0.0006 (16)	0.0017 (16)	−0.0023 (15)
N1	0.0285 (17)	0.0302 (17)	0.0299 (16)	−0.0032 (14)	0.0007 (14)	−0.0023 (13)
N2	0.039 (2)	0.0275 (15)	0.0280 (15)	0.0007 (15)	0.0003 (15)	0.0006 (12)
N3	0.033 (2)	0.0352 (17)	0.048 (2)	−0.0046 (15)	−0.0046 (17)	0.0044 (16)
O1	0.0576 (19)	0.0460 (14)	0.0230 (10)	−0.0053 (14)	0.0017 (13)	0.0067 (12)
O2	0.055 (2)	0.0506 (17)	0.0330 (14)	−0.0166 (16)	−0.0152 (14)	0.0102 (13)
O3	0.0468 (18)	0.0461 (16)	0.0317 (15)	−0.0126 (15)	−0.0016 (14)	0.0054 (12)
O4	0.0430 (16)	0.0320 (13)	0.0232 (12)	0.0027 (14)	−0.0013 (13)	0.0044 (10)
O5	0.071 (2)	0.074 (2)	0.065 (2)	−0.033 (2)	−0.028 (2)	0.0109 (17)
O6	0.0497 (19)	0.0505 (17)	0.066 (2)	−0.0139 (18)	0.0029 (18)	0.0110 (16)
O7	0.0437 (17)	0.0507 (16)	0.0266 (12)	0.0078 (15)	−0.0028 (14)	0.0012 (12)

Geometric parameters (Å, º)

Mn1—O1	2.074 (3)	C10—N1	1.329 (5)
Mn1—O3^i	2.429 (3)	C10—H10	0.9300
Mn1—O4^i	2.195 (3)	C11—C16	1.378 (5)
Mn1—O7	2.108 (3)	C11—C12	1.386 (5)
Mn1—N1	2.250 (3)	C11—C17	1.515 (5)
Mn1—N2	2.267 (3)	C12—C13	1.373 (5)
C1—N2	1.334 (5)	C12—H12	0.9300
C1—C2	1.373 (6)	C13—C14	1.404 (5)
C1—H1	0.9300	C13—C18	1.497 (5)
C2—C3	1.369 (6)	C14—C15	1.383 (5)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.399 (7)	C15—C16	1.394 (5)
C3—H3	0.9300	C15—N3	1.454 (5)
C4—C5	1.381 (6)	C16—H16	0.9300
C4—H4	0.9300	C17—O2	1.241 (5)
C5—N2	1.345 (5)	C17—O1	1.258 (4)
C5—C6	1.513 (6)	C18—O3	1.246 (4)
C6—N1	1.327 (5)	C18—O4	1.280 (4)
C6—C7	1.384 (5)	N3—O6	1.207 (4)
C7—C8	1.329 (7)	N3—O5	1.226 (5)
C7—H7	0.9300	O3—Mn1^ii	2.429 (3)
C8—C9	1.393 (7)	O4—Mn1^ii	2.195 (3)
C8—H8	0.9300	O7—H7A	0.866 (18)
C9—C10	1.381 (5)	O7—H7B	0.841 (18)
C9—H9	0.9300
O1—Mn1—O3^i	154.81 (10)	N1—C10—C9	123.1 (4)
O1—Mn1—O4^i	100.09 (10)	N1—C10—H10	118.5
O1—Mn1—O7	93.96 (11)	C9—C10—H10	118.5
O1—Mn1—N1	88.61 (11)	C16—C11—C12	119.5 (3)
O1—Mn1—N2	106.68 (11)	C16—C11—C17	119.8 (3)
O4^i—Mn1—O3^i	56.56 (10)	C12—C11—C17	120.7 (3)
O4^i—Mn1—N1	161.78 (11)	C13—C12—C11	121.4 (3)
O4^i—Mn1—N2	89.65 (10)	C13—C12—H12	119.3
O7—Mn1—O3^i	80.59 (10)	C11—C12—H12	119.3
O7—Mn1—O4^i	95.90 (11)	C12—C13—C14	120.0 (3)
O7—Mn1—N1	99.45 (12)	C12—C13—C18	121.3 (3)
O7—Mn1—N2	157.37 (12)	C14—C13—C18	118.7 (3)
N1—Mn1—O3^i	116.50 (10)	C15—C14—C13	118.1 (3)
N1—Mn1—N2	72.46 (12)	C15—C14—H14	121.0
N2—Mn1—O3^i	84.30 (10)	C13—C14—H14	121.0
N2—C1—C2	123.7 (4)	C14—C15—C16	121.9 (4)
N2—C1—H1	118.1	C14—C15—N3	119.0 (3)
C2—C1—H1	118.1	C16—C15—N3	119.1 (3)
C3—C2—C1	118.4 (4)	C11—C16—C15	119.2 (3)
C3—C2—H2	120.8	C11—C16—H16	120.4
C1—C2—H2	120.8	C15—C16—H16	120.4
C2—C3—C4	119.0 (4)	O2—C17—O1	125.4 (4)
C2—C3—H3	120.5	O2—C17—C11	118.5 (3)
C4—C3—H3	120.5	O1—C17—C11	116.1 (4)
C5—C4—C3	118.9 (4)	O3—C18—O4	121.2 (3)
C5—C4—H4	120.5	O3—C18—C13	120.3 (3)
C3—C4—H4	120.5	O4—C18—C13	118.5 (3)
N2—C5—C4	121.7 (4)	C6—N1—C10	118.3 (3)
N2—C5—C6	115.2 (3)	C6—N1—Mn1	118.2 (3)
C4—C5—C6	123.1 (4)	C10—N1—Mn1	122.6 (3)
N1—C6—C7	121.5 (4)	C1—N2—C5	118.1 (3)
N1—C6—C5	116.0 (3)	C1—N2—Mn1	124.2 (3)
C7—C6—C5	122.5 (4)	C5—N2—Mn1	117.6 (3)
C8—C7—C6	120.3 (5)	O6—N3—O5	124.1 (4)
C8—C7—H7	119.8	O6—N3—C15	118.6 (3)
C6—C7—H7	119.8	O5—N3—C15	117.2 (3)
C7—C8—C9	119.4 (4)	C17—O1—Mn1	147.2 (2)
C7—C8—H8	120.3	C18—O3—Mn1^ii	86.2 (2)
C9—C8—H8	120.3	C18—O4—Mn1^ii	96.0 (2)
C10—C9—C8	117.3 (4)	Mn1—O7—H7A	122 (2)
C10—C9—H9	121.3	Mn1—O7—H7B	124 (2)
C8—C9—H9	121.3	H7A—O7—H7B	109 (3)
N2—C1—C2—C3	0.4 (6)	O7—Mn1—N1—C6	−165.2 (3)
C1—C2—C3—C4	−1.1 (7)	O4^i—Mn1—N1—C6	−18.1 (5)
C2—C3—C4—C5	2.5 (7)	N2—Mn1—N1—C6	−7.0 (2)
C3—C4—C5—N2	−3.3 (7)	O3^i—Mn1—N1—C6	−81.1 (3)
C3—C4—C5—C6	178.3 (4)	O1—Mn1—N1—C10	−67.5 (3)
N2—C5—C6—N1	−5.5 (5)	O7—Mn1—N1—C10	26.3 (3)
C4—C5—C6—N1	173.0 (4)	O4^i—Mn1—N1—C10	173.4 (3)
N2—C5—C6—C7	172.2 (4)	N2—Mn1—N1—C10	−175.5 (3)
C4—C5—C6—C7	−9.3 (6)	O3^i—Mn1—N1—C10	110.4 (3)
N1—C6—C7—C8	0.6 (7)	C2—C1—N2—C5	−1.1 (6)
C5—C6—C7—C8	−177.0 (4)	C2—C1—N2—Mn1	−179.3 (3)
C6—C7—C8—C9	−2.2 (7)	C4—C5—N2—C1	2.5 (6)
C7—C8—C9—C10	2.8 (7)	C6—C5—N2—C1	−179.0 (3)
C8—C9—C10—N1	−2.0 (7)	C4—C5—N2—Mn1	−179.1 (3)
C16—C11—C12—C13	1.1 (5)	C6—C5—N2—Mn1	−0.6 (4)
C17—C11—C12—C13	−178.4 (3)	O1—Mn1—N2—C1	99.0 (3)
C11—C12—C13—C14	−0.5 (5)	O7—Mn1—N2—C1	−106.1 (4)
C11—C12—C13—C18	178.5 (3)	O4^i—Mn1—N2—C1	−1.4 (3)
C12—C13—C14—C15	−1.0 (5)	N1—Mn1—N2—C1	−178.0 (3)
C18—C13—C14—C15	180.0 (3)	O3^i—Mn1—N2—C1	−57.9 (3)
C13—C14—C15—C16	1.9 (6)	O1—Mn1—N2—C5	−79.3 (3)
C13—C14—C15—N3	−177.8 (3)	O7—Mn1—N2—C5	75.6 (4)
C12—C11—C16—C15	−0.2 (5)	O4^i—Mn1—N2—C5	−179.7 (3)
C17—C11—C16—C15	179.3 (4)	N1—Mn1—N2—C5	3.7 (3)
C14—C15—C16—C11	−1.3 (6)	O3^i—Mn1—N2—C5	123.9 (3)
N3—C15—C16—C11	178.5 (3)	C14—C15—N3—O6	−168.8 (4)
C16—C11—C17—O2	174.0 (3)	C16—C15—N3—O6	11.4 (5)
C12—C11—C17—O2	−6.4 (5)	C14—C15—N3—O5	11.6 (5)
C16—C11—C17—O1	−4.9 (5)	C16—C15—N3—O5	−168.1 (4)
C12—C11—C17—O1	174.6 (3)	O2—C17—O1—Mn1	58.4 (7)
C12—C13—C18—O3	2.0 (5)	C11—C17—O1—Mn1	−122.7 (4)
C14—C13—C18—O3	−179.0 (3)	O7—Mn1—O1—C17	62.8 (5)
C12—C13—C18—O4	−177.3 (3)	O4^i—Mn1—O1—C17	−33.9 (5)
C14—C13—C18—O4	1.7 (5)	N1—Mn1—O1—C17	162.2 (5)
C7—C6—N1—C10	0.3 (6)	N2—Mn1—O1—C17	−126.6 (5)
C5—C6—N1—C10	178.0 (3)	O3^i—Mn1—O1—C17	−13.4 (7)
C7—C6—N1—Mn1	−168.7 (3)	O4—C18—O3—Mn1^ii	−1.6 (3)
C5—C6—N1—Mn1	9.0 (4)	C13—C18—O3—Mn1^ii	179.1 (3)
C9—C10—N1—C6	0.5 (6)	O3—C18—O4—Mn1^ii	1.8 (4)
C9—C10—N1—Mn1	169.0 (3)	C13—C18—O4—Mn1^ii	−178.9 (3)
O1—Mn1—N1—C6	101.0 (3)

Symmetry codes: (i) −x+3/2, −y+2, z+1/2; (ii) −x+3/2, −y+2, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O4^iii	0.85 (2)	1.95 (2)	2.794 (4)	163 (3)
O7—H7B···O2^iv	0.85 (2)	1.83 (2)	2.655 (4)	169 (3)

Symmetry codes: (iii) −x+1/2, −y+2, z+1/2; (iv) x−1, y, z.