Literature DB >> 21202378

Quinoxaline-3-amino-phenol-water (2/1/2).

Agnieszka Czapik1, Maria Gdaniec.   

Abstract

The asymmetric unit of the title compound, 2C(8)H(6)N(2)·C(6)H(7)NO·2H(2)O, contains two quinoxaline mol-ecules, one mol-ecule of 3-amino-phenol and two water mol-ecules which are hydrogen bonded to form a two-dimensional polymeric structure. Each of the symmetry-independent quinoxaline mol-ecules forms separate stacks of different symmetry. In one set of stacks, the mol-ecules are related by a screw axis and are slightly tilted [dihedral angle = 7.12 (1)°]. In the second set of stacks, adjacent mol-ecules are parallel and related by an inversion center [inter-planar distances = 3.376 (4) and 3.473 (4) Å].

Entities:  

Year:  2008        PMID： 21202378      PMCID： PMC2961097          DOI： 10.1107/S1600536808010568

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For supra­molecular ladders, see: Sokolov & MacGillivray (2006 ▶); Sokolov et al. (2006 ▶). For complexes of aromatic diaza­heterocycles with phenols, see: Thalladi et al. (2000 ▶); Kadzewski & Gdaniec (2006 ▶).

Experimental

Crystal data

2C8H6N2·C6H7NO·2H2O M = 405.45 Monoclinic, a = 15.2951 (10) Å b = 7.1383 (4) Å c = 20.1614 (14) Å β = 110.775 (8)° V = 2058.1 (3) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 130.0 (2) K 0.40 × 0.40 × 0.07 mm

Data collection

Kuma KM-4-CCD κ-geometry diffractometer Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.966, T max = 1.000 (expected range = 0.960–0.994) 16706 measured reflections 3620 independent reflections 2285 reflections with I > 2σ(I) R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.031 wR(F 2) = 0.070 S = 0.91 3620 reflections 300 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.20 e Å−3 Δρmin = −0.14 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808010568/fl2194sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010568/fl2194Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
2C8H6N2·C6H7NO·2H2OF000 = 856
Mr = 405.45Dx = 1.309 Mg m−3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5665 reflections
a = 15.2951 (10) Åθ = 2.1–27.9º
b = 7.1383 (4) ŵ = 0.09 mm−1
c = 20.1614 (14) ÅT = 130.0 (2) K
β = 110.775 (8)ºPlate, colourless
V = 2058.1 (3) Å30.40 × 0.40 × 0.07 mm
Z = 4
Kuma KM-4-CCD κ-geometry diffractometer3620 independent reflections
Radiation source: fine-focus sealed tube2285 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.037
T = 130(2) Kθmax = 25.0º
ω scansθmin = 4.1º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)h = −18→17
Tmin = 0.966, Tmax = 1.000k = −8→8
16706 measured reflectionsl = −23→23
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.031  w = 1/[σ2(Fo2) + (0.0362P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.070(Δ/σ)max = 0.001
S = 0.91Δρmax = 0.20 e Å−3
3620 reflectionsΔρmin = −0.14 e Å−3
300 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0029 (5)
Secondary atom site location: difference Fourier map
Experimental. Absorption correction: SCALE3 ABSPACK scaling algorithm of the Crysalis RED program (Oxford Diffraction, 2007)
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.
xyzUiso*/Ueq
N1A0.40385 (8)0.19751 (16)0.55810 (6)0.0257 (3)
C2A0.33478 (10)0.1595 (2)0.49872 (7)0.0268 (4)
H2A0.27670.12840.50080.032*
C3A0.34523 (10)0.1639 (2)0.43241 (8)0.0272 (4)
H3A0.29370.13540.39230.033*
N4A0.42444 (8)0.20642 (17)0.42434 (6)0.0257 (3)
C5A0.58438 (10)0.3015 (2)0.48061 (8)0.0295 (4)
H5A0.59170.30430.43680.035*
C6A0.65726 (10)0.3465 (2)0.54049 (9)0.0346 (4)
H6A0.71440.37990.53730.042*
C7A0.64723 (10)0.3431 (2)0.60726 (8)0.0346 (4)
H7A0.69770.37440.64770.042*
C8A0.56397 (10)0.2943 (2)0.61310 (8)0.0295 (4)
H8A0.55780.29250.65740.035*
C9A0.48741 (9)0.24661 (19)0.55196 (7)0.0223 (3)
C10A0.49775 (9)0.25055 (19)0.48513 (7)0.0215 (3)
N1B−0.01606 (8)0.88628 (16)0.35287 (6)0.0237 (3)
C2B−0.10425 (10)0.88544 (19)0.34628 (7)0.0257 (4)
H2B−0.11940.89230.38700.031*
C3B−0.17739 (10)0.8745 (2)0.27975 (8)0.0294 (4)
H3B−0.23880.87490.27850.035*
N4B−0.16252 (8)0.86390 (17)0.21969 (6)0.0297 (3)
C5B−0.04863 (11)0.8530 (2)0.16312 (7)0.0312 (4)
H5B−0.09640.84530.11910.037*
C6B0.04198 (11)0.8538 (2)0.16717 (8)0.0333 (4)
H6B0.05580.84870.12590.040*
C7B0.11481 (11)0.8625 (2)0.23343 (8)0.0331 (4)
H7B0.17660.86170.23570.040*
C8B0.09583 (10)0.8720 (2)0.29450 (8)0.0294 (4)
H8B0.14450.87750.33810.035*
C9B0.00272 (9)0.87338 (19)0.29139 (7)0.0210 (3)
C10B−0.07063 (10)0.86356 (19)0.22497 (7)0.0229 (3)
C1C0.15035 (9)0.7993 (2)0.52107 (7)0.0208 (3)
O1C0.11852 (7)0.96292 (14)0.48513 (5)0.0286 (3)
H1C0.0737 (11)0.936 (2)0.4413 (9)0.061 (6)*
C2C0.22485 (9)0.8116 (2)0.58454 (7)0.0217 (3)
H2C0.25110.92800.60070.026*
C3C0.26114 (9)0.6520 (2)0.62471 (7)0.0240 (4)
N1C0.33268 (10)0.6689 (2)0.68974 (8)0.0443 (4)
H2NC0.3584 (10)0.561 (2)0.7146 (8)0.044 (5)*
H1NC0.3613 (10)0.780 (2)0.6997 (8)0.037 (5)*
C4C0.22258 (9)0.4776 (2)0.59862 (7)0.0274 (4)
H4C0.24720.36900.62380.033*
C5C0.14761 (10)0.4673 (2)0.53511 (7)0.0268 (4)
H5C0.12180.35090.51830.032*
C6C0.11020 (9)0.6262 (2)0.49608 (7)0.0249 (4)
H6C0.05920.61760.45390.030*
O1D0.40947 (7)0.06594 (16)0.69381 (7)0.0325 (3)
H1D0.4028 (12)0.121 (3)0.6539 (11)0.071 (7)*
H2D0.4209 (13)0.161 (3)0.7281 (11)0.089 (8)*
O1E0.43284 (8)0.14985 (16)0.28706 (6)0.0320 (3)
H1E0.4870 (14)0.078 (3)0.2927 (10)0.086 (7)*
H2E0.4315 (12)0.175 (3)0.3316 (11)0.077 (7)*
U11U22U33U12U13U23
N1A0.0264 (7)0.0255 (8)0.0254 (7)−0.0008 (5)0.0097 (6)0.0018 (5)
C2A0.0243 (8)0.0269 (10)0.0292 (9)−0.0017 (7)0.0095 (7)0.0011 (7)
C3A0.0255 (9)0.0251 (10)0.0263 (9)−0.0008 (7)0.0036 (7)−0.0005 (7)
N4A0.0280 (7)0.0239 (7)0.0249 (7)0.0011 (5)0.0090 (6)0.0006 (5)
C5A0.0293 (9)0.0268 (10)0.0378 (10)0.0035 (7)0.0185 (8)0.0019 (7)
C6A0.0228 (9)0.0256 (10)0.0568 (12)−0.0007 (7)0.0158 (8)−0.0005 (8)
C7A0.0274 (9)0.0274 (10)0.0396 (10)0.0002 (7)0.0001 (8)−0.0030 (8)
C8A0.0312 (9)0.0283 (9)0.0253 (9)−0.0006 (7)0.0054 (7)−0.0015 (7)
C9A0.0239 (8)0.0169 (9)0.0256 (9)0.0009 (6)0.0083 (7)0.0018 (6)
C10A0.0247 (8)0.0155 (9)0.0248 (9)0.0030 (6)0.0094 (7)0.0005 (6)
N1B0.0234 (7)0.0231 (8)0.0242 (7)0.0012 (5)0.0078 (6)0.0024 (5)
C2B0.0298 (9)0.0242 (9)0.0269 (9)0.0032 (7)0.0146 (7)0.0049 (7)
C3B0.0218 (8)0.0331 (10)0.0348 (10)0.0012 (7)0.0120 (7)0.0063 (7)
N4B0.0254 (7)0.0345 (9)0.0283 (7)0.0002 (6)0.0083 (6)0.0050 (6)
C5B0.0410 (10)0.0298 (10)0.0233 (9)0.0000 (7)0.0120 (8)0.0015 (7)
C6B0.0486 (11)0.0281 (10)0.0331 (10)0.0024 (8)0.0266 (8)0.0046 (7)
C7B0.0314 (9)0.0270 (10)0.0492 (11)0.0029 (7)0.0246 (8)0.0043 (8)
C8B0.0233 (9)0.0296 (10)0.0339 (9)0.0026 (7)0.0084 (7)0.0029 (7)
C9B0.0241 (8)0.0164 (8)0.0235 (8)0.0019 (6)0.0099 (7)0.0027 (6)
C10B0.0261 (8)0.0183 (9)0.0247 (8)0.0013 (6)0.0093 (7)0.0038 (6)
C1C0.0210 (8)0.0218 (9)0.0215 (8)0.0031 (7)0.0100 (7)0.0026 (7)
O1C0.0286 (6)0.0246 (7)0.0255 (6)−0.0010 (5)0.0009 (5)0.0019 (5)
C2C0.0192 (8)0.0232 (9)0.0239 (8)−0.0042 (6)0.0088 (6)−0.0024 (6)
C3C0.0173 (8)0.0311 (10)0.0243 (8)−0.0010 (7)0.0082 (7)0.0038 (7)
N1C0.0365 (9)0.0366 (10)0.0408 (9)−0.0100 (8)−0.0099 (7)0.0144 (8)
C4C0.0256 (9)0.0270 (10)0.0314 (9)0.0025 (7)0.0124 (7)0.0085 (7)
C5C0.0298 (9)0.0236 (9)0.0294 (9)−0.0049 (7)0.0136 (7)−0.0030 (7)
C6C0.0244 (8)0.0272 (10)0.0221 (8)−0.0031 (7)0.0069 (7)−0.0014 (7)
O1D0.0400 (7)0.0326 (7)0.0252 (7)−0.0059 (5)0.0119 (5)−0.0024 (6)
O1E0.0382 (7)0.0348 (7)0.0229 (6)0.0000 (5)0.0106 (5)0.0005 (5)
N1A—C2A1.3136 (16)C6B—C7B1.405 (2)
N1A—C9A1.3725 (17)C6B—H6B0.9300
C2A—C3A1.402 (2)C7B—C8B1.363 (2)
C2A—H2A0.9300C7B—H7B0.9300
C3A—N4A1.3138 (17)C8B—C9B1.4031 (18)
C3A—H3A0.9300C8B—H8B0.9300
N4A—C10A1.3726 (16)C9B—C10B1.4111 (18)
C5A—C6A1.3597 (19)C1C—O1C1.3697 (16)
C5A—C10A1.4078 (18)C1C—C2C1.3818 (17)
C5A—H5A0.9300C1C—C6C1.3919 (19)
C6A—C7A1.408 (2)O1C—H1C0.927 (17)
C6A—H6A0.9300C2C—C3C1.3940 (19)
C7A—C8A1.365 (2)C2C—H2C0.9300
C7A—H7A0.9300C3C—N1C1.3832 (18)
C8A—C9A1.4080 (18)C3C—C4C1.398 (2)
C8A—H8A0.9300N1C—H2NC0.927 (16)
C9A—C10A1.4116 (19)N1C—H1NC0.891 (16)
N1B—C2B1.3077 (16)C4C—C5C1.3850 (18)
N1B—C9B1.3711 (17)C4C—H4C0.9300
C2B—C3B1.4114 (19)C5C—C6C1.3839 (19)
C2B—H2B0.9300C5C—H5C0.9300
C3B—N4B1.3112 (18)C6C—H6C0.9300
C3B—H3B0.9300O1D—H1D0.87 (2)
N4B—C10B1.3714 (16)O1D—H2D0.94 (2)
C5B—C6B1.3591 (19)O1E—H1E0.95 (2)
C5B—C10B1.404 (2)O1E—H2E0.92 (2)
C5B—H5B0.9300
C2A—N1A—C9A116.37 (12)C5B—C6B—H6B119.8
N1A—C2A—C3A122.51 (14)C7B—C6B—H6B119.8
N1A—C2A—H2A118.7C8B—C7B—C6B120.66 (14)
C3A—C2A—H2A118.7C8B—C7B—H7B119.7
N4A—C3A—C2A123.05 (13)C6B—C7B—H7B119.7
N4A—C3A—H3A118.5C7B—C8B—C9B119.86 (14)
C2A—C3A—H3A118.5C7B—C8B—H8B120.1
C3A—N4A—C10A116.07 (12)C9B—C8B—H8B120.1
C6A—C5A—C10A119.83 (15)N1B—C9B—C8B119.66 (12)
C6A—C5A—H5A120.1N1B—C9B—C10B120.68 (12)
C10A—C5A—H5A120.1C8B—C9B—C10B119.65 (13)
C5A—C6A—C7A120.79 (15)N4B—C10B—C5B119.54 (13)
C5A—C6A—H6A119.6N4B—C10B—C9B121.44 (13)
C7A—C6A—H6A119.6C5B—C10B—C9B119.02 (13)
C8A—C7A—C6A120.54 (14)O1C—C1C—C2C117.20 (13)
C8A—C7A—H7A119.7O1C—C1C—C6C122.48 (12)
C6A—C7A—H7A119.7C2C—C1C—C6C120.32 (13)
C7A—C8A—C9A119.86 (14)C1C—O1C—H1C109.2 (11)
C7A—C8A—H8A120.1C1C—C2C—C3C120.90 (13)
C9A—C8A—H8A120.1C1C—C2C—H2C119.6
N1A—C9A—C8A119.65 (13)C3C—C2C—H2C119.6
N1A—C9A—C10A120.96 (12)N1C—C3C—C2C119.84 (14)
C8A—C9A—C10A119.40 (13)N1C—C3C—C4C121.36 (14)
N4A—C10A—C5A119.40 (13)C2C—C3C—C4C118.78 (13)
N4A—C10A—C9A121.01 (13)C3C—N1C—H2NC118.7 (10)
C5A—C10A—C9A119.59 (13)C3C—N1C—H1NC116.8 (10)
C2B—N1B—C9B116.56 (11)H2NC—N1C—H1NC122.4 (14)
N1B—C2B—C3B122.56 (14)C5C—C4C—C3C119.71 (13)
N1B—C2B—H2B118.7C5C—C4C—H4C120.1
C3B—C2B—H2B118.7C3C—C4C—H4C120.1
N4B—C3B—C2B122.83 (14)C6C—C5C—C4C121.45 (14)
N4B—C3B—H3B118.6C6C—C5C—H5C119.3
C2B—C3B—H3B118.6C4C—C5C—H5C119.3
C3B—N4B—C10B115.92 (12)C5C—C6C—C1C118.79 (13)
C6B—C5B—C10B120.46 (14)C5C—C6C—H6C120.6
C6B—C5B—H5B119.8C1C—C6C—H6C120.6
C10B—C5B—H5B119.8H1D—O1D—H2D106.6 (18)
C5B—C6B—C7B120.34 (14)H1E—O1E—H2E107.9 (16)
D—H···AD—HH···AD···AD—H···A
O1C—H1C···N1B0.927 (17)1.857 (17)2.7844 (14)178.7 (16)
N1C—H2NC···O1Ei0.927 (16)2.125 (17)3.0400 (19)168.8 (14)
N1C—H1NC···O1Dii0.891 (16)2.191 (17)3.058 (2)164.4 (13)
O1D—H1D···N1A0.87 (2)2.01 (2)2.8651 (17)166.8 (17)
O1D—H2D···O1Ei0.94 (2)1.77 (2)2.7022 (16)174.5 (19)
O1E—H1E···O1Diii0.95 (2)1.82 (2)2.7711 (17)177.8 (19)
O1E—H2E···N4A0.92 (2)1.92 (2)2.8446 (16)175.4 (18)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1C—H1C⋯N1B0.927 (17)1.857 (17)2.7844 (14)178.7 (16)
N1C—H2NC⋯O1Ei0.927 (16)2.125 (17)3.0400 (19)168.8 (14)
N1C—H1NC⋯O1Dii0.891 (16)2.191 (17)3.058 (2)164.4 (13)
O1D—H1D⋯N1A0.87 (2)2.01 (2)2.8651 (17)166.8 (17)
O1D—H2D⋯O1Ei0.94 (2)1.77 (2)2.7022 (16)174.5 (19)
O1E—H1E⋯O1Diii0.95 (2)1.82 (2)2.7711 (17)177.8 (19)
O1E—H2E⋯N4A0.92 (2)1.92 (2)2.8446 (16)175.4 (18)

Symmetry codes: (i) ; (ii) ; (iii) .

  1 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290
  1 in total
  1 in total

1.  Phenazine-naphthalene-1,5-diamine-water (1/1/2).

Authors:  Agnieszka Czapik; Maria Gdaniec
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-11-21
  1 in total

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