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In the title compound, C12H8N2·C4H6O6·3H2O, the mol­ecules are linked by strong O—H...O hydrogen bonds and π–π inter­actions, generating an infinite three-dimensional framework.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806018824/bh2009sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806018824/bh2009Isup2.hkl
Contains datablock I

CCDC reference: 610691

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.053
  • wR factor = 0.140
  • Data-to-parameter ratio = 7.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H6 .. H71 .. 1.60 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.34 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.52 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.36 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT731_ALERT_1_C Bond Calc 0.82(5), Rep 0.82(2) ...... 2.50 su-Rat O3 -H3 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.87(4), Rep 0.870(19) ...... 2.11 su-Rat O9 -H92 1.555 1.555
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 26.00 From the CIF: _reflns_number_total 2011 Count of symmetry unique reflns 2018 Completeness (_total/calc) 99.65% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

1,10-phenanthroline–(L)-(+)-tartaric acid–water (1/1/3) top
Crystal data top
C12H8N2·C4H6O6·3H2OF(000) = 808
Mr = 384.34Dx = 1.436 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1518 reflections
a = 7.1625 (11) Åθ = 2.6–22.2°
b = 12.680 (2) ŵ = 0.12 mm1
c = 19.573 (5) ÅT = 293 K
V = 1777.6 (6) Å3Block, colourless
Z = 40.30 × 0.30 × 0.20 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2011 independent reflections
Radiation source: fine-focus sealed tube1607 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 88
Tmin = 0.965, Tmax = 0.977k = 1415
7952 measured reflectionsl = 1124
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0766P)2 + 0.2889P]
where P = (Fo2 + 2Fc2)/3
2011 reflections(Δ/σ)max < 0.001
274 parametersΔρmax = 0.35 e Å3
13 restraintsΔρmin = 0.23 e Å3
Special details top

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
C10.9452 (8)0.4536 (4)0.4662 (2)0.0661 (13)
H1A0.94790.50780.43410.079*
C20.9442 (9)0.4779 (5)0.5354 (3)0.0759 (16)
H2A0.94170.54780.54990.091*
C30.9468 (8)0.3989 (5)0.5812 (2)0.0711 (15)
H3A0.94890.41460.62760.085*
C40.9464 (7)0.2919 (4)0.55991 (19)0.0573 (12)
C50.9474 (9)0.2019 (5)0.6053 (2)0.0748 (16)
H5A0.95120.21320.65230.090*
C60.9432 (9)0.1049 (5)0.5824 (2)0.0729 (15)
H6A0.94400.04940.61340.088*
C70.9371 (7)0.0819 (4)0.51048 (19)0.0534 (11)
C80.9305 (7)0.0203 (4)0.4835 (2)0.0609 (12)
H8A0.92930.07830.51260.073*
C90.9260 (7)0.0344 (4)0.4151 (2)0.0585 (12)
H9A0.91900.10190.39660.070*
C100.9320 (7)0.0541 (3)0.3726 (2)0.0538 (11)
H10A0.93010.04340.32560.065*
C110.9403 (6)0.1668 (3)0.46375 (17)0.0431 (9)
C120.9435 (6)0.2724 (3)0.48962 (18)0.0448 (10)
N10.9402 (6)0.1519 (3)0.39513 (15)0.0489 (9)
N20.9423 (6)0.3549 (3)0.44526 (16)0.0482 (9)
C130.4354 (5)0.7462 (3)0.34306 (17)0.0407 (9)
C140.2251 (5)0.7480 (3)0.34342 (17)0.0341 (8)
H14A0.18350.81910.33120.041*
C150.1454 (5)0.6705 (3)0.29162 (17)0.0321 (8)
H15A0.18750.69110.24590.039*
C160.0690 (5)0.6725 (3)0.29308 (15)0.0298 (7)
O10.5233 (5)0.7205 (5)0.39333 (15)0.1003 (17)
O20.5130 (3)0.7725 (2)0.28563 (13)0.0417 (7)
H20.623 (3)0.758 (4)0.291 (2)0.062*
O30.1543 (4)0.7233 (3)0.40861 (12)0.0522 (8)
H30.221 (7)0.749 (4)0.438 (2)0.078*
O40.2043 (4)0.5661 (2)0.30431 (15)0.0478 (7)
H40.306 (4)0.553 (4)0.285 (2)0.072*
O50.1543 (4)0.5913 (2)0.30408 (17)0.0550 (8)
O60.1415 (3)0.7618 (2)0.28281 (14)0.0398 (6)
H60.105 (6)0.794 (3)0.2501 (16)0.060*
O70.9307 (5)0.3803 (2)0.31070 (15)0.0519 (8)
H711.046 (3)0.369 (4)0.312 (2)0.078*
H720.917 (7)0.4470 (18)0.316 (3)0.078*
O80.8169 (5)0.7045 (3)0.47615 (13)0.0639 (9)
H810.908 (5)0.710 (6)0.450 (2)0.096*
H820.722 (5)0.711 (5)0.449 (2)0.096*
O90.5312 (4)0.5047 (2)0.24350 (16)0.0562 (8)
H910.574 (7)0.442 (2)0.240 (3)0.084*
H920.612 (6)0.533 (3)0.271 (2)0.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.084 (4)0.051 (3)0.063 (3)0.008 (3)0.001 (3)0.008 (2)
C20.088 (4)0.070 (4)0.070 (3)0.016 (4)0.012 (3)0.027 (3)
C30.062 (3)0.105 (4)0.047 (2)0.000 (4)0.002 (3)0.023 (3)
C40.050 (3)0.085 (3)0.0362 (19)0.002 (3)0.003 (2)0.014 (2)
C50.085 (4)0.111 (5)0.0279 (19)0.004 (4)0.001 (2)0.005 (2)
C60.099 (4)0.080 (4)0.040 (2)0.005 (4)0.002 (3)0.020 (2)
C70.052 (3)0.066 (3)0.042 (2)0.002 (3)0.001 (2)0.014 (2)
C80.064 (3)0.053 (3)0.066 (3)0.002 (3)0.002 (3)0.020 (2)
C90.066 (3)0.046 (3)0.064 (3)0.006 (2)0.002 (3)0.004 (2)
C100.068 (3)0.047 (3)0.046 (2)0.012 (3)0.000 (2)0.0003 (18)
C110.042 (2)0.051 (2)0.0359 (18)0.003 (2)0.0012 (17)0.0043 (17)
C120.037 (2)0.060 (3)0.0373 (18)0.000 (2)0.0011 (17)0.0002 (18)
N10.063 (2)0.049 (2)0.0348 (15)0.010 (2)0.0032 (17)0.0029 (14)
N20.056 (2)0.042 (2)0.0469 (18)0.0049 (19)0.0022 (18)0.0032 (15)
C130.0248 (17)0.061 (3)0.0366 (17)0.001 (2)0.0006 (15)0.0048 (18)
C140.0265 (17)0.044 (2)0.0323 (16)0.0002 (16)0.0013 (13)0.0032 (16)
C150.0230 (16)0.037 (2)0.0368 (17)0.0021 (16)0.0023 (14)0.0030 (16)
C160.0223 (16)0.039 (2)0.0280 (15)0.0008 (17)0.0008 (13)0.0002 (15)
O10.0378 (18)0.225 (6)0.0378 (15)0.010 (3)0.0049 (13)0.016 (2)
O20.0245 (12)0.0544 (17)0.0460 (13)0.0017 (12)0.0001 (11)0.0124 (13)
O30.0312 (14)0.092 (2)0.0328 (12)0.0056 (17)0.0042 (11)0.0104 (14)
O40.0398 (16)0.0391 (16)0.0644 (18)0.0113 (14)0.0029 (13)0.0039 (13)
O50.0329 (14)0.0385 (16)0.094 (2)0.0082 (13)0.0017 (16)0.0106 (15)
O60.0244 (12)0.0404 (16)0.0544 (15)0.0008 (12)0.0028 (11)0.0118 (12)
O70.0624 (19)0.0378 (16)0.0555 (15)0.0011 (16)0.0064 (16)0.0011 (13)
O80.0426 (18)0.112 (3)0.0373 (14)0.001 (2)0.0030 (13)0.0044 (17)
O90.0494 (18)0.0523 (19)0.0668 (19)0.0030 (16)0.0055 (16)0.0052 (15)
Geometric parameters (Å, º) top
C1—N21.317 (6)C12—N21.359 (5)
C1—C21.391 (7)C13—O11.212 (5)
C1—H1A0.9300C13—O21.298 (4)
C2—C31.344 (8)C13—C141.507 (5)
C2—H2A0.9300C14—O31.408 (4)
C3—C41.419 (8)C14—C151.523 (5)
C3—H3A0.9300C14—H14A0.9800
C4—C121.398 (5)C15—O41.411 (5)
C4—C51.447 (8)C15—C161.536 (5)
C5—C61.310 (8)C15—H15A0.9800
C5—H5A0.9300C16—O51.217 (4)
C6—C71.438 (6)C16—O61.263 (4)
C6—H6A0.9300O2—H20.82 (2)
C7—C81.400 (7)O3—H30.82 (2)
C7—C111.413 (6)O4—H40.84 (2)
C8—C91.350 (6)O6—H60.80 (2)
C8—H8A0.9300O7—H710.84 (2)
C9—C101.398 (6)O7—H720.858 (19)
C9—H9A0.9300O8—H810.83 (2)
C10—N11.317 (6)O8—H820.87 (2)
C10—H10A0.9300O9—H910.86 (2)
C11—N11.356 (5)O9—H920.870 (19)
C11—C121.432 (6)
N2—C1—C2120.9 (5)C7—C11—C12119.0 (3)
N2—C1—H1A119.6N2—C12—C4119.5 (4)
C2—C1—H1A119.6N2—C12—C11119.6 (3)
C3—C2—C1119.0 (5)C4—C12—C11120.9 (4)
C3—C2—H2A120.5C10—N1—C11117.5 (4)
C1—C2—H2A120.5C1—N2—C12122.2 (4)
C2—C3—C4121.1 (4)O1—C13—O2123.4 (3)
C2—C3—H3A119.4O1—C13—C14121.3 (3)
C4—C3—H3A119.4O2—C13—C14115.3 (3)
C12—C4—C3117.3 (4)O3—C14—C13111.1 (3)
C12—C4—C5117.7 (4)O3—C14—C15108.9 (3)
C3—C4—C5125.0 (4)C13—C14—C15111.2 (3)
C6—C5—C4122.0 (4)O3—C14—H14A108.5
C6—C5—H5A119.0C13—C14—H14A108.5
C4—C5—H5A119.0C15—C14—H14A108.5
C5—C6—C7121.8 (4)O4—C15—C14112.1 (3)
C5—C6—H6A119.1O4—C15—C16108.1 (3)
C7—C6—H6A119.1C14—C15—C16110.6 (3)
C8—C7—C11117.5 (4)O4—C15—H15A108.7
C8—C7—C6123.9 (4)C14—C15—H15A108.7
C11—C7—C6118.6 (4)C16—C15—H15A108.7
C9—C8—C7119.8 (4)O5—C16—O6125.5 (3)
C9—C8—H8A120.1O5—C16—C15119.5 (3)
C7—C8—H8A120.1O6—C16—C15115.0 (3)
C8—C9—C10118.8 (4)C13—O2—H2104 (3)
C8—C9—H9A120.6C14—O3—H3110 (4)
C10—C9—H9A120.6C15—O4—H4111 (4)
N1—C10—C9123.9 (4)C16—O6—H6117 (3)
N1—C10—H10A118.0H71—O7—H72106 (3)
C9—C10—H10A118.0H81—O8—H82104 (3)
N1—C11—C7122.3 (4)H91—O9—H92101 (3)
N1—C11—C12118.7 (3)
N2—C1—C2—C32.3 (10)C7—C11—C12—N2178.5 (4)
C1—C2—C3—C41.4 (10)N1—C11—C12—C4179.1 (4)
C2—C3—C4—C120.1 (8)C7—C11—C12—C41.0 (6)
C2—C3—C4—C5179.4 (6)C9—C10—N1—C110.9 (8)
C12—C4—C5—C60.9 (9)C7—C11—N1—C101.8 (7)
C3—C4—C5—C6178.6 (6)C12—C11—N1—C10178.2 (4)
C4—C5—C6—C70.0 (11)C2—C1—N2—C121.9 (9)
C5—C6—C7—C8179.3 (6)C4—C12—N2—C10.5 (7)
C5—C6—C7—C111.5 (9)C11—C12—N2—C1180.0 (5)
C11—C7—C8—C90.5 (8)O1—C13—C14—O33.6 (7)
C6—C7—C8—C9179.7 (5)O2—C13—C14—O3177.2 (3)
C7—C8—C9—C101.3 (9)O1—C13—C14—C15118.0 (5)
C8—C9—C10—N10.7 (9)O2—C13—C14—C1561.3 (5)
C8—C7—C11—N11.1 (7)O3—C14—C15—O464.1 (4)
C6—C7—C11—N1178.2 (5)C13—C14—C15—O458.7 (4)
C8—C7—C11—C12178.8 (4)O3—C14—C15—C1656.6 (4)
C6—C7—C11—C121.9 (7)C13—C14—C15—C16179.4 (3)
C3—C4—C12—N20.4 (7)O4—C15—C16—O50.1 (5)
C5—C4—C12—N2179.9 (5)C14—C15—C16—O5123.0 (4)
C3—C4—C12—C11179.1 (5)O4—C15—C16—O6179.6 (3)
C5—C4—C12—C110.4 (7)C14—C15—C16—O656.5 (4)
N1—C11—C12—N21.4 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O90.84 (3)1.91 (3)2.740 (4)173 (5)
O8—H82···O10.87 (4)1.80 (4)2.663 (5)178 (6)
O2—H2···O6i0.82 (2)1.70 (2)2.479 (3)161 (4)
O3—H3···O8ii0.82 (4)1.91 (4)2.699 (4)163 (5)
O6—H6···O7iii0.80 (3)2.04 (4)2.808 (4)159 (4)
O7—H72···O4i0.86 (2)2.56 (4)3.067 (4)119 (4)
O7—H72···O5i0.86 (2)1.91 (3)2.747 (4)163 (6)
O7—H71···O6iv0.84 (2)2.41 (4)2.808 (4)110 (3)
O8—H81···O3i0.83 (4)1.95 (4)2.765 (4)167 (4)
O9—H91···O2iv0.86 (3)2.29 (3)3.016 (5)142 (4)
O9—H92···O5i0.88 (4)1.94 (4)2.772 (4)159 (4)
Symmetry codes: (i) x+1, y, z; (ii) x1/2, y+3/2, z+1; (iii) x+1, y+1/2, z+1/2; (iv) x+1, y1/2, z+1/2.
 

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