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The title compound, C17H12N4O4·2CH4O, crystallizes with the main mol­ecule lying on a twofold axis (through the methyl­ene bridge C atom) and two methanol solvent mol­ecules in general positions. Inter­molecular O—H...O and C—H...O inter­actions are present, with the methanol mol­ecules acting as O—H hydrogen-bond donors and acceptors.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806040748/gg2011sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806040748/gg2011Isup2.hkl
Contains datablock I

CCDC reference: 627665

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.050
  • wR factor = 0.145
  • Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
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 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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: SHELXTL (Sheldrick, 2000).

4-hydroxy-2-((4-hydroxy-1-oxo-phthalazin-2(1H)-yl)methyl)phthalazin-1(2H)-one methanol disolvate top
Crystal data top
C17H12N4O4·2CH4OF(000) = 840
Mr = 400.39Dx = 1.452 Mg m3
Monoclinic, C2/cMelting point: 483 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 22.233 (3) ÅCell parameters from 3146 reflections
b = 4.8390 (5) Åθ = 2.4–28.1°
c = 18.438 (2) ŵ = 0.11 mm1
β = 112.575 (2)°T = 292 K
V = 1831.7 (4) Å3Block, colourless
Z = 40.30 × 0.20 × 0.10 mm
Data collection top
Bruker CCD
diffractometer
1603 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.065
Graphite monochromatorθmax = 28.0°, θmin = 2.0°
φ and ω scansh = 2828
10103 measured reflectionsk = 66
2172 independent reflectionsl = 2424
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0922P)2]
where P = (Fo2 + 2Fc2)/3
2172 reflections(Δ/σ)max = 0.001
139 parametersΔρmax = 0.30 e Å3
2 restraintsΔρmin = 0.17 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*/UeqOcc. (<1)
C10.61156 (7)0.4012 (3)0.16963 (8)0.0367 (3)
C20.67646 (7)0.4076 (3)0.17633 (9)0.0469 (4)
H20.70710.29160.21170.056*
C30.69461 (8)0.5860 (3)0.13044 (10)0.0532 (4)
H30.73780.59100.13510.064*
C40.64895 (8)0.7591 (3)0.07696 (10)0.0515 (4)
H40.66170.87780.04580.062*
C50.58551 (8)0.7556 (3)0.07001 (9)0.0439 (4)
H50.55520.87220.03430.053*
C60.56622 (6)0.5768 (3)0.11647 (7)0.0354 (3)
C70.50018 (7)0.5652 (3)0.11315 (7)0.0363 (3)
C80.59175 (7)0.2148 (3)0.21859 (8)0.0363 (3)
C90.50000.0522 (4)0.25000.0384 (4)
H9A0.53390.06550.28540.046*0.50
H9B0.46610.06550.21460.046*0.50
C100.31193 (9)0.5752 (4)0.09034 (12)0.0656 (5)
H10A0.33940.41530.09910.098*
H10B0.27560.55660.04110.098*
H10C0.29630.59140.13200.098*
N10.48065 (5)0.3982 (2)0.15399 (6)0.0379 (3)
N20.52689 (5)0.2229 (2)0.20508 (7)0.0356 (3)
O10.45781 (5)0.7440 (2)0.06499 (6)0.0461 (3)
H10.4239 (7)0.751 (4)0.0729 (13)0.069*
O20.62978 (5)0.0574 (2)0.26805 (6)0.0482 (3)
O30.34797 (5)0.8140 (2)0.08866 (7)0.0512 (3)
H3A0.3577 (10)0.905 (4)0.1301 (8)0.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0386 (7)0.0365 (7)0.0368 (7)0.0001 (6)0.0163 (6)0.0057 (5)
C20.0385 (8)0.0519 (9)0.0509 (9)0.0029 (6)0.0179 (7)0.0007 (7)
C30.0422 (8)0.0610 (11)0.0635 (10)0.0050 (7)0.0280 (8)0.0030 (8)
C40.0560 (10)0.0495 (9)0.0577 (10)0.0090 (7)0.0315 (8)0.0004 (7)
C50.0475 (8)0.0431 (9)0.0420 (8)0.0016 (6)0.0183 (7)0.0026 (6)
C60.0385 (7)0.0358 (7)0.0318 (7)0.0022 (5)0.0134 (6)0.0063 (5)
C70.0407 (7)0.0360 (8)0.0317 (7)0.0031 (6)0.0134 (6)0.0025 (5)
C80.0368 (7)0.0383 (7)0.0343 (7)0.0030 (6)0.0139 (6)0.0043 (5)
C90.0409 (10)0.0335 (10)0.0437 (10)0.0000.0194 (9)0.000
C100.0659 (11)0.0564 (11)0.0763 (12)0.0055 (9)0.0294 (10)0.0013 (9)
N10.0349 (6)0.0402 (7)0.0379 (6)0.0037 (5)0.0133 (5)0.0015 (5)
N20.0368 (6)0.0369 (6)0.0350 (6)0.0033 (5)0.0160 (5)0.0028 (4)
O10.0409 (6)0.0520 (7)0.0450 (6)0.0087 (5)0.0161 (5)0.0115 (5)
O20.0434 (6)0.0534 (7)0.0492 (6)0.0124 (5)0.0192 (5)0.0124 (5)
O30.0484 (7)0.0530 (7)0.0535 (7)0.0005 (5)0.0210 (5)0.0030 (5)
Geometric parameters (Å, º) top
C1—C61.3929 (19)C8—O21.2387 (16)
C1—C21.4006 (19)C8—N21.3665 (17)
C1—C81.459 (2)C9—N21.4509 (15)
C2—C31.373 (2)C9—N2i1.4510 (15)
C2—H20.9300C9—H9A0.9700
C3—C41.392 (2)C9—H9B0.9700
C3—H30.9300C10—O31.414 (2)
C4—C51.366 (2)C10—H10A0.9600
C4—H40.9300C10—H10B0.9600
C5—C61.396 (2)C10—H10C0.9600
C5—H50.9300N1—N21.3859 (15)
C6—C71.4469 (18)O1—H10.822 (9)
C7—N11.2882 (18)O3—H3A0.834 (9)
C7—O11.3350 (16)
C6—C1—C2119.43 (13)O2—C8—N2121.74 (13)
C6—C1—C8120.26 (12)O2—C8—C1123.57 (13)
C2—C1—C8120.31 (13)N2—C8—C1114.68 (12)
C3—C2—C1119.74 (14)N2—C9—N2i110.64 (15)
C3—C2—H2120.1N2—C9—H9A109.5
C1—C2—H2120.1N2i—C9—H9A109.5
C2—C3—C4120.54 (14)N2—C9—H9B109.5
C2—C3—H3119.7N2i—C9—H9B109.5
C4—C3—H3119.7H9A—C9—H9B108.1
C5—C4—C3120.32 (14)O3—C10—H10A109.5
C5—C4—H4119.8O3—C10—H10B109.5
C3—C4—H4119.8H10A—C10—H10B109.5
C4—C5—C6119.97 (14)O3—C10—H10C109.5
C4—C5—H5120.0H10A—C10—H10C109.5
C6—C5—H5120.0H10B—C10—H10C109.5
C1—C6—C5120.00 (13)C7—N1—N2116.92 (11)
C1—C6—C7117.04 (12)C8—N2—N1126.65 (11)
C5—C6—C7122.96 (13)C8—N2—C9121.13 (10)
N1—C7—O1119.03 (12)N1—N2—C9112.07 (9)
N1—C7—C6124.32 (12)C7—O1—H1111.6 (15)
O1—C7—C6116.64 (12)C10—O3—H3A111.2 (15)
C6—C1—C2—C30.2 (2)C6—C1—C8—O2178.55 (12)
C8—C1—C2—C3179.37 (13)C2—C1—C8—O20.7 (2)
C1—C2—C3—C40.4 (2)C6—C1—C8—N22.40 (18)
C2—C3—C4—C50.6 (3)C2—C1—C8—N2178.39 (12)
C3—C4—C5—C60.3 (2)O1—C7—N1—N2177.89 (11)
C2—C1—C6—C50.5 (2)C6—C7—N1—N21.1 (2)
C8—C1—C6—C5179.73 (12)O2—C8—N2—N1176.96 (12)
C2—C1—C6—C7178.81 (12)C1—C8—N2—N13.96 (19)
C8—C1—C6—C70.41 (18)O2—C8—N2—C91.86 (19)
C4—C5—C6—C10.3 (2)C1—C8—N2—C9179.07 (11)
C4—C5—C6—C7178.98 (13)C7—N1—N2—C82.3 (2)
C1—C6—C7—N12.3 (2)C7—N1—N2—C9177.79 (11)
C5—C6—C7—N1178.37 (13)N2i—C9—N2—C8117.29 (12)
C1—C6—C7—O1176.68 (11)N2i—C9—N2—N158.48 (8)
C5—C6—C7—O12.62 (19)
Symmetry code: (i) x+1, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O30.82 (1)1.85 (1)2.6621 (16)173 (2)
O3—H3A···O2ii0.83 (1)1.94 (1)2.7583 (16)168 (2)
C5—H5···O1iii0.932.553.3387 (18)143
C9—H9A···O20.972.352.7748 (10)106
Symmetry codes: (ii) x+1, y+1, z+1/2; (iii) x+1, y+2, z.
 

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