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In the title compound, 2C2H8N+·C10H4O82−·2C12H8N2, dimethyl­ammonium cations, 2,5-dicarboxy­benzene-1,4-dicarboxyl­ate anions and 1,10-phenanthroline mol­ecules are linked by N—H...N and N—H...O hydrogen bonds into a network structure. The 2,5-dicarboxy­benzene-1,4-dicarboxyl­ate anion lies on an inversion center.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807004783/fj2001sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807004783/fj2001Isup2.hkl
Contains datablock I

CCDC reference: 614277

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.047
  • wR factor = 0.120
  • Data-to-parameter ratio = 12.3

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: AINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Bis(dimethylammonium) 2,5-dicarboxybenzene-1,4-dicarboxylate bis(1,10-phenanthroline) top
Crystal data top
2C12H8N2+·C10H4O82·2C2H8NZ = 1
Mr = 704.73F(000) = 370
Triclinic, P1Dx = 1.393 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1333 (10) ÅCell parameters from 4483 reflections
b = 9.3392 (14) Åθ = 2.3–25.1°
c = 13.1127 (19) ŵ = 0.10 mm1
α = 74.543 (2)°T = 298 K
β = 88.942 (3)°Prism, colourless
γ = 86.179 (3)°0.32 × 0.15 × 0.08 mm
V = 840.1 (2) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
2962 independent reflections
Radiation source: fine-focus sealed tube2346 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
ω scansθmax = 25.1°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 88
Tmin = 0.980, Tmax = 0.990k = 1111
4483 measured reflectionsl = 1512
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.063P)2 + 0.0799P]
where P = (Fo2 + 2Fc2)/3
2962 reflections(Δ/σ)max < 0.001
240 parametersΔρmax = 0.16 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
C50.2854 (3)0.0028 (3)1.15541 (16)0.0626 (6)
H50.28990.04171.22850.075*
C60.3214 (3)0.1388 (3)1.11381 (17)0.0616 (6)
H60.35040.19701.15820.074*
C170.8377 (3)0.3058 (2)0.57458 (13)0.0449 (4)
N10.19096 (19)0.12123 (17)0.91349 (12)0.0449 (4)
C120.2339 (2)0.0386 (2)0.97916 (13)0.0409 (4)
N20.2663 (2)0.16961 (16)0.82680 (12)0.0454 (4)
C110.2741 (2)0.1151 (2)0.93369 (13)0.0413 (4)
O10.8255 (2)0.17515 (14)0.57223 (11)0.0609 (4)
C140.6669 (2)0.41345 (17)0.53936 (12)0.0354 (4)
C130.5482 (2)0.37538 (17)0.46960 (12)0.0386 (4)
H130.58120.28950.44860.046*
C70.3163 (2)0.2031 (2)1.00132 (16)0.0503 (5)
C150.6169 (2)0.54343 (17)0.57116 (12)0.0366 (4)
O20.98412 (18)0.35243 (17)0.60385 (12)0.0637 (4)
O30.8962 (2)0.56751 (16)0.66754 (12)0.0664 (4)
H30.950 (3)0.468 (3)0.631 (2)0.100*
C40.2397 (2)0.0967 (2)1.09053 (14)0.0502 (5)
C10.1532 (3)0.2607 (2)0.95730 (17)0.0544 (5)
H10.12330.31830.91270.065*
C160.7198 (3)0.6079 (2)0.64786 (15)0.0512 (5)
O40.6367 (2)0.69657 (19)0.68733 (14)0.0828 (5)
C30.1978 (3)0.2453 (3)1.13124 (17)0.0624 (6)
H3A0.19960.28761.20400.075*
C80.3502 (3)0.3519 (3)0.9542 (2)0.0650 (6)
H80.37780.41390.99600.078*
C100.3005 (3)0.3105 (2)0.78643 (18)0.0559 (5)
H100.29610.34820.71330.067*
C20.1549 (3)0.3274 (2)1.06579 (19)0.0630 (6)
H20.12710.42631.09240.076*
C90.3429 (3)0.4061 (2)0.8467 (2)0.0669 (6)
H90.36560.50480.81450.080*
N30.15141 (19)1.00663 (15)0.67303 (11)0.0440 (4)
H3B0.17281.01120.73950.053*
H3C0.05831.07530.64570.053*
C190.0911 (3)0.8588 (2)0.67628 (17)0.0634 (6)
H19A0.06730.85340.60560.095*
H19B0.02170.84130.71760.095*
H19C0.18800.78480.70780.095*
C180.3229 (3)1.0427 (3)0.60939 (19)0.0718 (6)
H18A0.42370.97140.63920.108*
H18B0.35631.14060.60950.108*
H18C0.30041.03970.53810.108*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C50.0457 (11)0.1032 (19)0.0414 (11)0.0146 (11)0.0039 (9)0.0277 (12)
C60.0406 (10)0.1016 (18)0.0577 (13)0.0075 (11)0.0060 (9)0.0500 (13)
C170.0516 (11)0.0494 (11)0.0293 (9)0.0062 (8)0.0002 (8)0.0052 (8)
N10.0404 (8)0.0504 (9)0.0444 (9)0.0005 (7)0.0016 (7)0.0142 (7)
C120.0291 (8)0.0561 (11)0.0379 (10)0.0070 (7)0.0010 (7)0.0158 (8)
N20.0420 (8)0.0491 (9)0.0445 (9)0.0008 (7)0.0045 (7)0.0119 (7)
C110.0282 (8)0.0561 (11)0.0433 (10)0.0051 (7)0.0028 (7)0.0215 (8)
O10.0778 (10)0.0468 (8)0.0570 (9)0.0190 (7)0.0124 (7)0.0165 (6)
C140.0411 (9)0.0346 (9)0.0285 (8)0.0022 (7)0.0019 (7)0.0051 (7)
C130.0512 (10)0.0307 (9)0.0342 (9)0.0010 (7)0.0028 (8)0.0099 (7)
C70.0313 (9)0.0684 (13)0.0621 (13)0.0037 (8)0.0034 (8)0.0374 (10)
C150.0450 (9)0.0332 (9)0.0310 (9)0.0058 (7)0.0005 (7)0.0065 (7)
O20.0496 (8)0.0690 (9)0.0689 (10)0.0078 (7)0.0154 (7)0.0140 (8)
O30.0652 (9)0.0636 (9)0.0738 (10)0.0085 (7)0.0275 (8)0.0210 (8)
C40.0337 (9)0.0744 (14)0.0396 (10)0.0123 (9)0.0004 (8)0.0136 (10)
C10.0474 (11)0.0521 (12)0.0620 (13)0.0010 (9)0.0007 (9)0.0134 (10)
C160.0656 (13)0.0438 (10)0.0458 (11)0.0071 (9)0.0110 (9)0.0130 (9)
O40.0939 (12)0.0891 (12)0.0878 (12)0.0047 (9)0.0217 (9)0.0633 (10)
C30.0489 (11)0.0792 (16)0.0461 (12)0.0125 (10)0.0060 (9)0.0018 (11)
C80.0430 (11)0.0736 (15)0.0948 (18)0.0022 (10)0.0044 (11)0.0510 (14)
C100.0476 (11)0.0526 (12)0.0647 (13)0.0021 (9)0.0016 (10)0.0106 (10)
C20.0503 (12)0.0571 (13)0.0698 (15)0.0040 (9)0.0071 (10)0.0014 (11)
C90.0493 (12)0.0511 (12)0.103 (2)0.0038 (9)0.0002 (12)0.0250 (13)
N30.0510 (9)0.0440 (8)0.0377 (8)0.0077 (7)0.0059 (7)0.0143 (6)
C190.0793 (15)0.0557 (12)0.0628 (14)0.0120 (11)0.0091 (11)0.0277 (10)
C180.0725 (15)0.0779 (16)0.0682 (15)0.0156 (12)0.0179 (12)0.0238 (12)
Geometric parameters (Å, º) top
C5—C61.330 (3)O3—H31.19 (3)
C5—C41.430 (3)C4—C31.398 (3)
C5—H50.9300C1—C21.393 (3)
C6—C71.437 (3)C1—H10.9300
C6—H60.9300C16—O41.207 (2)
C17—O11.238 (2)C3—C21.345 (3)
C17—O21.262 (2)C3—H3A0.9300
C17—C141.523 (2)C8—C91.365 (3)
N1—C11.320 (2)C8—H80.9300
N1—C121.351 (2)C10—C91.391 (3)
C12—C41.416 (2)C10—H100.9300
C12—C111.446 (3)C2—H20.9300
N2—C101.318 (2)C9—H90.9300
N2—C111.359 (2)N3—C191.463 (2)
C11—C71.409 (2)N3—C181.474 (2)
C14—C131.386 (2)N3—H3B0.9000
C14—C151.408 (2)N3—H3C0.9000
C13—C15i1.391 (2)C19—H19A0.9600
C13—H130.9300C19—H19B0.9600
C7—C81.397 (3)C19—H19C0.9600
C15—C13i1.391 (2)C18—H18A0.9600
C15—C161.523 (2)C18—H18B0.9600
O2—H31.23 (3)C18—H18C0.9600
O3—C161.300 (2)
C6—C5—C4121.6 (2)O4—C16—O3121.77 (18)
C6—C5—H5119.2O4—C16—C15119.38 (18)
C4—C5—H5119.2O3—C16—C15118.83 (17)
C5—C6—C7120.95 (19)C2—C3—C4120.4 (2)
C5—C6—H6119.5C2—C3—H3A119.8
C7—C6—H6119.5C4—C3—H3A119.8
O1—C17—O2123.01 (17)C9—C8—C7120.02 (19)
O1—C17—C14117.48 (16)C9—C8—H8120.0
O2—C17—C14119.51 (17)C7—C8—H8120.0
C1—N1—C12117.18 (16)N2—C10—C9123.9 (2)
N1—C12—C4122.51 (17)N2—C10—H10118.0
N1—C12—C11118.55 (15)C9—C10—H10118.0
C4—C12—C11118.94 (16)C3—C2—C1118.4 (2)
C10—N2—C11117.69 (16)C3—C2—H2120.8
N2—C11—C7122.55 (17)C1—C2—H2120.8
N2—C11—C12118.28 (15)C8—C9—C10118.6 (2)
C7—C11—C12119.16 (17)C8—C9—H9120.7
C13—C14—C15117.71 (14)C10—C9—H9120.7
C13—C14—C17115.11 (15)C19—N3—C18112.67 (15)
C15—C14—C17127.17 (15)C19—N3—H3B109.1
C14—C13—C15i124.62 (15)C18—N3—H3B109.1
C14—C13—H13117.7C19—N3—H3C109.1
C15i—C13—H13117.7C18—N3—H3C109.1
C8—C7—C11117.25 (19)H3B—N3—H3C107.8
C8—C7—C6122.97 (19)N3—C19—H19A109.5
C11—C7—C6119.78 (19)N3—C19—H19B109.5
C13i—C15—C14117.67 (15)H19A—C19—H19B109.5
C13i—C15—C16114.14 (15)N3—C19—H19C109.5
C14—C15—C16128.17 (15)H19A—C19—H19C109.5
C17—O2—H3111.8 (11)H19B—C19—H19C109.5
C16—O3—H3112.7 (12)N3—C18—H18A109.5
C3—C4—C12117.07 (18)N3—C18—H18B109.5
C3—C4—C5123.4 (2)H18A—C18—H18B109.5
C12—C4—C5119.58 (19)N3—C18—H18C109.5
N1—C1—C2124.4 (2)H18A—C18—H18C109.5
N1—C1—H1117.8H18B—C18—H18C109.5
C2—C1—H1117.8
C4—C5—C6—C70.2 (3)C13—C14—C15—C16178.76 (16)
C1—N1—C12—C40.2 (2)C17—C14—C15—C160.1 (3)
C1—N1—C12—C11179.35 (15)N1—C12—C4—C30.3 (2)
C10—N2—C11—C70.2 (2)C11—C12—C4—C3179.27 (15)
C10—N2—C11—C12179.04 (14)N1—C12—C4—C5179.72 (15)
N1—C12—C11—N20.2 (2)C11—C12—C4—C50.2 (2)
C4—C12—C11—N2179.39 (14)C6—C5—C4—C3178.89 (18)
N1—C12—C11—C7179.06 (14)C6—C5—C4—C120.5 (3)
C4—C12—C11—C70.5 (2)C12—N1—C1—C20.1 (3)
O1—C17—C14—C1325.4 (2)C13i—C15—C16—O417.6 (3)
O2—C17—C14—C13154.09 (16)C14—C15—C16—O4161.12 (19)
O1—C17—C14—C15153.45 (16)C13i—C15—C16—O3161.16 (16)
O2—C17—C14—C1527.0 (3)C14—C15—C16—O320.1 (3)
C15—C14—C13—C15i0.0 (3)C12—C4—C3—C20.2 (3)
C17—C14—C13—C15i178.97 (15)C5—C4—C3—C2179.63 (18)
N2—C11—C7—C80.2 (2)C11—C7—C8—C90.4 (3)
C12—C11—C7—C8178.65 (15)C6—C7—C8—C9179.89 (18)
N2—C11—C7—C6179.69 (15)C11—N2—C10—C90.4 (3)
C12—C11—C7—C60.9 (2)C4—C3—C2—C10.1 (3)
C5—C6—C7—C8178.94 (17)N1—C1—C2—C30.0 (3)
C5—C6—C7—C110.5 (3)C7—C8—C9—C100.2 (3)
C13—C14—C15—C13i0.0 (2)N2—C10—C9—C80.2 (3)
C17—C14—C15—C13i178.84 (15)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3C···O2ii0.902.523.262 (2)140
N3—H3C···O1ii0.901.982.8541 (19)163
N3—H3B···N1iii0.902.293.071 (2)145
N3—H3B···N2iii0.902.242.986 (2)140
O3—H3···O21.19 (3)1.23 (3)2.415 (2)170 (2)
Symmetry codes: (ii) x1, y+1, z; (iii) x, y+1, z.
 

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