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In the title compound, C6H4N2.C7H4ClNO4, the two components are connected by an O—H...N hydrogen bond. In the crystal structure, the mol­ecules are stacked in columns held together by three different π–π stacking interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804021087/wn6275sup1.cif
Contains datablocks General, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804021087/wn6275Isup2.hkl
Contains datablock I

CCDC reference: 252959

Key indicators

  • Single-crystal X-ray study
  • T = 300 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.051
  • wR factor = 0.119
  • Data-to-parameter ratio = 16.0

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.18 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C9 - C13 ... 1.44 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 2 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

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1990); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997-1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

(I) top
Crystal data top
C6H4N2·C7H4ClNO4F(000) = 624.0
Mr = 305.67Dx = 1.504 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 10.012 (3) Åθ = 11.5–12.1°
b = 10.318 (3) ŵ = 0.30 mm1
c = 13.974 (2) ÅT = 300 K
β = 110.767 (15)°Prism, colorless
V = 1349.7 (6) Å30.40 × 0.30 × 0.30 mm
Z = 4
Data collection top
Rigaku AFC-5R
diffractometer
1692 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anodeRint = 0.021
Graphite monochromatorθmax = 27.5°, θmin = 2.2°
ω–2θ scansh = 113
Absorption correction: ψ scan
(North et al., 1968)
k = 013
Tmin = 0.898, Tmax = 0.915l = 1817
3633 measured reflections3 standard reflections every 97 reflections
3103 independent reflections intensity decay: 4.8%
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.04P)2 + 0.45P]
where P = (Fo2 + 2Fc2)/3
3103 reflections(Δ/σ)max = 0.001
194 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.25 e Å3
0 constraints
Special details top

Experimental. The scan width was (1.68 + 0.30tanθ)° with an ω scan speed of 6° per minute (up to 3 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

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
Cl0.24621 (11)0.60956 (8)0.08116 (6)0.0770 (3)
O10.4477 (2)0.29136 (19)0.24162 (13)0.0619 (6)
O20.5200 (2)0.4925 (2)0.23403 (14)0.0597 (6)
O30.1397 (2)0.4539 (2)0.29062 (14)0.0637 (6)
O40.2499 (2)0.2733 (2)0.28571 (13)0.0625 (6)
N10.2182 (3)0.3664 (2)0.24438 (16)0.0472 (6)
N20.6406 (2)0.4696 (2)0.43469 (15)0.0452 (6)
N30.5637 (3)0.1709 (3)0.6690 (2)0.0819 (10)
C10.3913 (3)0.3872 (2)0.07832 (17)0.0380 (6)
C20.2977 (3)0.4822 (2)0.02162 (18)0.0434 (7)
C30.2399 (3)0.4758 (3)0.08426 (18)0.0454 (7)
C40.2784 (3)0.3730 (3)0.13161 (16)0.0389 (6)
C50.3696 (3)0.2777 (3)0.07910 (18)0.0444 (7)
C60.4245 (3)0.2853 (3)0.02654 (18)0.0442 (7)
C70.4549 (3)0.3859 (3)0.19374 (17)0.0411 (6)
C80.6006 (3)0.3731 (3)0.48122 (18)0.0432 (7)
C90.6538 (3)0.3595 (3)0.58716 (19)0.0420 (6)
C100.7534 (3)0.4475 (3)0.64607 (19)0.0475 (7)
C110.7945 (3)0.5465 (3)0.59704 (19)0.0504 (7)
C120.7353 (3)0.5546 (3)0.4918 (2)0.0499 (7)
C130.6048 (3)0.2544 (3)0.6336 (2)0.0545 (8)
H10.564 (4)0.480 (4)0.307 (3)0.127 (15)*
H20.17700.53890.12210.055*
H30.39420.20970.11340.053*
H40.48530.22030.06360.053*
H50.53510.31270.44190.052*
H60.79130.43980.71700.057*
H70.86150.60720.63420.060*
H80.76290.62270.45930.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.1210 (8)0.0572 (5)0.0425 (4)0.0305 (5)0.0164 (4)0.0053 (4)
O10.0881 (16)0.0538 (13)0.0338 (10)0.0154 (12)0.0093 (10)0.0049 (9)
O20.0802 (15)0.0563 (13)0.0299 (9)0.0255 (12)0.0039 (10)0.0005 (9)
O30.0755 (15)0.0686 (14)0.0329 (10)0.0061 (13)0.0018 (10)0.0079 (10)
O40.0776 (16)0.0683 (14)0.0360 (10)0.0002 (12)0.0134 (10)0.0150 (10)
N10.0515 (16)0.0566 (15)0.0287 (10)0.0131 (13)0.0082 (10)0.0025 (11)
N20.0504 (15)0.0527 (14)0.0288 (10)0.0004 (12)0.0095 (10)0.0005 (10)
N30.084 (2)0.090 (2)0.0625 (18)0.0195 (18)0.0151 (16)0.0241 (16)
C10.0415 (15)0.0423 (14)0.0269 (11)0.0074 (13)0.0081 (11)0.0031 (11)
C20.0588 (18)0.0379 (14)0.0318 (12)0.0008 (14)0.0140 (12)0.0024 (11)
C30.0549 (18)0.0440 (15)0.0314 (12)0.0048 (14)0.0079 (12)0.0039 (12)
C40.0411 (15)0.0470 (16)0.0244 (11)0.0105 (13)0.0066 (11)0.0008 (11)
C50.0448 (17)0.0503 (16)0.0365 (13)0.0024 (14)0.0123 (12)0.0063 (12)
C60.0407 (16)0.0522 (17)0.0343 (13)0.0056 (14)0.0066 (12)0.0043 (12)
C70.0434 (16)0.0488 (16)0.0288 (12)0.0031 (14)0.0099 (11)0.0008 (12)
C80.0443 (17)0.0468 (16)0.0341 (12)0.0037 (13)0.0083 (12)0.0009 (12)
C90.0430 (16)0.0472 (16)0.0365 (13)0.0067 (13)0.0151 (12)0.0054 (12)
C100.0535 (19)0.0556 (18)0.0285 (12)0.0066 (15)0.0086 (13)0.0003 (12)
C110.0542 (18)0.0552 (17)0.0354 (14)0.0070 (15)0.0080 (13)0.0051 (13)
C120.060 (2)0.0495 (17)0.0396 (14)0.0048 (15)0.0166 (14)0.0028 (13)
C130.057 (2)0.060 (2)0.0409 (15)0.0006 (16)0.0108 (14)0.0069 (14)
Geometric parameters (Å, º) top
Cl—C21.729 (3)N2—C121.330 (3)
O1—C71.200 (3)N3—C131.140 (4)
O2—C71.300 (3)C8—C91.391 (3)
O2—H10.96 (4)C9—C101.383 (4)
O3—N11.221 (3)C9—C131.437 (4)
O4—N11.220 (3)C10—C111.372 (4)
N1—C41.476 (3)C11—C121.379 (3)
C1—C61.381 (4)C3—H20.93
C1—C21.394 (3)C5—H30.93
C1—C71.509 (3)C6—H40.93
C2—C31.386 (3)C8—H50.93
C3—C41.375 (4)C10—H60.93
C4—C51.366 (4)C11—H70.93
C5—C61.383 (3)C12—H80.93
N2—C81.326 (3)
O1···N1i3.106 (4)O2···C4ii3.178 (4)
O2···N22.641 (3)O2···O4ii3.239 (3)
O2···N1ii2.957 (4)
C7—O2—H1108 (3)C1—C6—H4119.2
O4—N1—O3124.0 (2)C5—C6—H4119.2
O4—N1—C4117.8 (2)O1—C7—O2124.5 (2)
O3—N1—C4118.3 (2)O1—C7—C1121.1 (2)
C8—N2—C12118.4 (2)O2—C7—C1114.3 (2)
C6—C1—C2118.4 (2)N2—C8—C9121.9 (3)
C6—C1—C7117.7 (2)N2—C8—H5119.0
C2—C1—C7123.8 (2)C9—C8—H5119.0
C3—C2—C1121.0 (2)C10—C9—C8119.4 (3)
C3—C2—Cl117.9 (2)C10—C9—C13121.1 (2)
C1—C2—Cl121.10 (19)C8—C9—C13119.6 (3)
C4—C3—C2117.9 (2)C11—C10—C9118.2 (2)
C4—C3—H2121.0C11—C10—H6120.9
C2—C3—H2121.0C9—C10—H6120.9
C5—C4—C3123.0 (2)C10—C11—C12119.1 (3)
C5—C4—N1118.9 (2)C10—C11—H7120.5
C3—C4—N1118.1 (2)C12—C11—H7120.5
C4—C5—C6118.0 (2)N2—C12—C11123.0 (3)
C4—C5—H3121.0N2—C12—H8118.5
C6—C5—H3121.0C11—C12—H8118.5
C1—C6—C5121.6 (3)N3—C13—C9178.8 (3)
C6—C1—C2—C30.5 (4)C7—C1—C6—C5179.1 (3)
C7—C1—C2—C3178.1 (3)C4—C5—C6—C11.4 (4)
C6—C1—C2—Cl177.7 (2)C6—C1—C7—O149.3 (4)
C7—C1—C2—Cl0.1 (4)C2—C1—C7—O1128.3 (3)
C1—C2—C3—C40.3 (4)C6—C1—C7—O2128.5 (3)
Cl—C2—C3—C4178.6 (2)C2—C1—C7—O253.9 (4)
C2—C3—C4—C50.4 (4)C12—N2—C8—C90.6 (4)
C2—C3—C4—N1179.4 (2)N2—C8—C9—C101.2 (4)
O4—N1—C4—C52.1 (4)N2—C8—C9—C13178.9 (3)
O3—N1—C4—C5178.1 (3)C8—C9—C10—C110.8 (4)
O4—N1—C4—C3178.2 (2)C13—C9—C10—C11179.3 (3)
O3—N1—C4—C31.7 (4)C9—C10—C11—C120.2 (4)
C3—C4—C5—C60.4 (4)C8—N2—C12—C110.5 (4)
N1—C4—C5—C6179.8 (2)C10—C11—C12—N20.9 (5)
C2—C1—C6—C51.4 (4)
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1···N20.97 (4)1.68 (4)2.641 (3)176 (4)
 

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