Literature DB >> 23476464

6-Eth-oxy-carbonyl-5,7-dihy-droxy-2,3-dihydro-1H-pyrido[3,2,1-ij]quinolinium tribromide.

Victor B Rybakov1, Svitlana V Shishkina, Igor V Ukrainets, Nikolai Yu Golik, Igor N Chernenok.   

Abstract

In the title salt, C15H16NO4(+.)Br3(-), classical intra-molecular O-H⋯O hydrogen bonds are found, which results in the co-planarity of the ester substituents with the quinolinium residue [C-C-C-O torsion angle = 1.0 (10)°]. The bromine anions are placed on both sides of heterocyclic cation and form Br⋯N contacts of 3.674 (9) and 3.860 (9) Å, which confirms the location of positive charge on the N atom. Non-classical inter-molecular C-H⋯Br inter-actions stabilize the three-dimensional crystal structure. Moreover, anion⋯π inter-actions are noted [Br⋯ring centroid range = 3.367 (9)-3.697 (9) Å]. The partly saturated heterocycle is disordered over two sofa conformations with occupancies in the ratio 0.56 (2):0.44 (2).

Entities:  

Year:  2012        PMID： 23476464      PMCID： PMC3588293          DOI： 10.1107/S1600536812049276

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


Related literature

For general background, see: Ukrainets et al. (2004 ▶, 2007 ▶). For chemical bond lengths, see: Bürgi & Dunitz (1994 ▶).

Experimental

Crystal data

C15H16NO4 +·Br3 − M = 513.99 Triclinic, a = 7.6491 (8) Å b = 9.1729 (10) Å c = 13.3722 (14) Å α = 102.355 (9)° β = 98.777 (9)° γ = 98.093 (9)° V = 891.06 (17) Å3 Z = 2 Mo Kα radiation μ = 6.81 mm−1 T = 295 K 0.20 × 0.05 × 0.05 mm

Data collection

Agilent Xcalibur-3 CCD diffractometer Absorption correction: multi-scan (CrysAlis RED; Agilent, 2011 ▶) T min = 0.343, T max = 0.727 10147 measured reflections 5106 independent reflections 1855 reflections with I > 2σ(I) R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.068 wR(F 2) = 0.217 S = 0.90 5106 reflections 224 parameters 5 restraints H-atom parameters constrained Δρmax = 1.02 e Å−3 Δρmin = −0.74 e Å−3 Data collection: CrysAlis CCD (Agilent, 2011 ▶); cell refinement: CrysAlis RED (Agilent, 2011 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL. Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812049276/aa2080sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049276/aa2080Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812049276/aa2080Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H16NO4+·Br3−Z = 2
Mr = 513.99F(000) = 500
Triclinic, P1Dx = 1.916 Mg m−3
Hall symbol: -P 1Melting point = 360–362 K
a = 7.6491 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.1729 (10) ÅCell parameters from 1363 reflections
c = 13.3722 (14) Åθ = 3.1–32.0°
α = 102.355 (9)°µ = 6.81 mm−1
β = 98.777 (9)°T = 295 K
γ = 98.093 (9)°Rod, light yellow
V = 891.06 (17) Å30.20 × 0.05 × 0.05 mm
Agilent Xcalibur-3 CCD diffractometer5106 independent reflections
Radiation source: Enhance (Mo) X-Ray Source1855 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
Detector resolution: 16.1827 pixels mm-1θmax = 30.0°, θmin = 3.1°
ω scansh = −10→10
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2011)k = −12→12
Tmin = 0.343, Tmax = 0.727l = −18→18
10147 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.068Hydrogen site location: difference Fourier map
wR(F2) = 0.217H-atom parameters constrained
S = 0.90w = 1/[σ2(Fo2) + (0.108P)2] where P = (Fo2 + 2Fc2)/3
5106 reflections(Δ/σ)max < 0.001
224 parametersΔρmax = 1.02 e Å−3
5 restraintsΔρmin = −0.74 e Å−3
Experimental. Absorption correction: CrysAlis RED (Agilent Technologies, 2011). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wRand 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 > 2σ(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*/UeqOcc. (<1)
Br10.50000.50000.50000.0803 (3)
Br20.56781 (11)0.74499 (9)0.44305 (6)0.1062 (4)
Br30.00000.00000.00000.1391 (6)
Br40.06301 (17)−0.24813 (17)0.03287 (9)0.1666 (6)
N10.1821 (7)0.3314 (6)0.2533 (4)0.0753 (14)
O10.4153 (7)0.3418 (7)0.1698 (5)0.1109 (17)
H10.49950.29860.15800.166*
O20.2437 (8)−0.0849 (6)0.3048 (4)0.0989 (14)
H20.3201−0.12170.27600.148*
O30.5774 (8)0.1288 (8)0.1341 (4)0.131 (2)
O40.5025 (7)−0.0768 (7)0.1961 (4)0.1052 (16)
C10.0665 (9)0.2577 (8)0.3053 (4)0.0726 (17)
C2−0.0723 (9)0.3279 (8)0.3413 (6)0.0848 (19)
C3−0.1792 (11)0.2510 (11)0.3935 (6)0.108 (2)
H3−0.26790.29720.42090.129*
C4−0.1624 (11)0.1110 (10)0.4074 (6)0.095 (2)
H4−0.24380.06100.43940.114*
C5−0.0296 (10)0.0449 (8)0.3754 (5)0.0853 (19)
H5−0.0136−0.04830.38880.102*
C60.0867 (9)0.1169 (8)0.3211 (4)0.0747 (17)
C70.2325 (9)0.0461 (8)0.2845 (5)0.0774 (17)
C80.3425 (9)0.1203 (8)0.2317 (5)0.0772 (17)
C90.3130 (10)0.2649 (9)0.2176 (5)0.085 (2)
C100.1679 (10)0.4818 (9)0.2325 (7)0.110 (3)
H10A0.19980.48490.16540.132*0.56 (2)
H10B0.25200.55970.28550.132*0.56 (2)
H10C0.10170.46910.16240.132*0.44 (2)
H10D0.28710.53890.23780.132*0.44 (2)
C11A−0.0241 (14)0.515 (2)0.2325 (11)0.113 (7)0.56 (2)
H11A−0.02230.62140.23530.136*0.56 (2)
H11B−0.10110.45690.16750.136*0.56 (2)
C11B0.0704 (18)0.5691 (14)0.3120 (14)0.117 (9)0.44 (2)
H11C0.15060.60190.37930.141*0.44 (2)
H11D0.04310.65910.29040.141*0.44 (2)
C12−0.1052 (12)0.4752 (10)0.3240 (7)0.126 (3)
H12A−0.05350.55360.38690.151*0.56 (2)
H12B−0.23380.47340.30990.151*0.56 (2)
H12C−0.14990.52960.38250.151*0.44 (2)
H12D−0.19560.45970.26150.151*0.44 (2)
C130.4866 (11)0.0567 (11)0.1831 (5)0.092 (2)
C140.6366 (11)−0.1428 (11)0.1409 (8)0.140 (4)
H14A0.7564−0.10790.18290.167*
H14B0.6352−0.11370.07520.167*
C150.5833 (15)−0.3161 (11)0.1218 (10)0.173 (5)
H15A0.6558−0.36490.07720.260*
H15B0.4588−0.34700.08930.260*
H15C0.6020−0.34440.18720.260*
U11U22U33U12U13U23
Br10.0730 (5)0.0913 (7)0.0716 (5)0.0189 (5)0.0020 (4)0.0143 (5)
Br20.1086 (6)0.0994 (7)0.1052 (6)0.0040 (5)0.0010 (4)0.0359 (5)
Br30.0870 (7)0.2340 (17)0.0652 (6)−0.0272 (9)−0.0029 (5)0.0175 (7)
Br40.1423 (10)0.2122 (13)0.1221 (8)−0.0008 (9)0.0014 (6)0.0283 (8)
N10.071 (3)0.071 (4)0.077 (3)−0.003 (3)0.004 (3)0.019 (3)
O10.098 (4)0.133 (5)0.108 (4)−0.009 (3)0.022 (3)0.061 (4)
O20.112 (4)0.082 (3)0.116 (4)0.034 (3)0.040 (3)0.028 (3)
O30.107 (4)0.179 (6)0.104 (4)−0.004 (4)0.050 (3)0.027 (4)
O40.083 (3)0.110 (4)0.114 (4)0.011 (3)0.031 (3)0.002 (3)
C10.076 (4)0.076 (4)0.055 (3)−0.003 (3)−0.006 (3)0.017 (3)
C20.084 (4)0.082 (5)0.099 (5)0.026 (4)0.020 (4)0.034 (4)
C30.095 (5)0.125 (7)0.103 (5)0.021 (5)0.035 (4)0.016 (5)
C40.096 (5)0.104 (6)0.095 (5)0.029 (5)0.040 (4)0.024 (4)
C50.097 (5)0.083 (5)0.081 (4)0.009 (4)0.023 (4)0.030 (4)
C60.086 (4)0.080 (5)0.052 (3)0.007 (4)−0.002 (3)0.019 (3)
C70.080 (4)0.076 (5)0.069 (4)0.007 (4)0.008 (3)0.012 (3)
C80.076 (4)0.084 (5)0.062 (3)0.002 (4)0.006 (3)0.010 (3)
C90.085 (5)0.096 (6)0.059 (3)−0.017 (4)−0.002 (3)0.019 (4)
C100.113 (6)0.086 (6)0.113 (6)−0.014 (5)−0.012 (5)0.027 (5)
C11A0.115 (13)0.103 (12)0.127 (14)0.022 (10)0.004 (10)0.052 (11)
C11B0.111 (16)0.081 (14)0.17 (2)0.015 (11)0.018 (16)0.060 (14)
C120.141 (8)0.099 (6)0.146 (8)0.029 (6)0.034 (6)0.038 (6)
C130.092 (5)0.102 (6)0.072 (4)0.014 (5)0.008 (4)0.009 (4)
C140.097 (6)0.154 (10)0.151 (8)0.033 (6)0.043 (6)−0.019 (7)
C150.176 (11)0.169 (12)0.232 (13)0.074 (10)0.106 (10)0.096 (11)
Br1—Br2i2.5346 (8)C7—C81.376 (9)
Br1—Br22.5346 (8)C8—C91.423 (10)
Br3—Br4ii2.5057 (16)C8—C131.489 (11)
Br3—Br42.5057 (16)C10—C11A1.5398 (10)
N1—C91.340 (9)C10—C11B1.5398 (10)
N1—C11.394 (8)C10—H10A0.9700
N1—C101.479 (9)C10—H10B0.9700
O1—C91.307 (8)C10—H10C0.9700
O1—H10.8200C10—H10D0.9700
O2—C71.299 (8)C11A—C121.5396 (10)
O2—H20.8200C11A—H11A0.9700
O3—C131.243 (10)C11A—H11B0.9700
O4—C131.292 (9)C11B—C121.5397 (10)
O4—C141.476 (9)C11B—H11C0.9700
C1—C61.378 (9)C11B—H11D0.9700
C1—C21.411 (10)C12—H12A0.9700
C2—C31.370 (10)C12—H12B0.9700
C2—C121.467 (11)C12—H12C0.9700
C3—C41.358 (10)C12—H12D0.9700
C3—H30.9300C14—C151.5395 (10)
C4—C51.334 (10)C14—H14A0.9700
C4—H40.9300C14—H14B0.9700
C5—C61.411 (9)C15—H15A0.9600
C5—H50.9300C15—H15B0.9600
C6—C71.462 (10)C15—H15C0.9600
Br2i—Br1—Br2180.0C11B—C10—H10D109.7
Br4ii—Br3—Br4180.00 (8)H10A—C10—H10D66.6
C9—N1—C1120.0 (6)H10C—C10—H10D108.2
C9—N1—C10116.4 (6)C12—C11A—C10113.6 (7)
C1—N1—C10123.6 (6)C12—C11A—H11A108.9
C9—O1—H1109.5C10—C11A—H11A108.9
C7—O2—H2109.5C12—C11A—H11B108.9
C13—O4—C14112.8 (7)C10—C11A—H11B108.9
C6—C1—N1120.4 (6)H11A—C11A—H11B107.7
C6—C1—C2120.1 (6)C12—C11B—C10113.6 (7)
N1—C1—C2119.5 (6)C12—C11B—H11C108.9
C3—C2—C1116.7 (7)C10—C11B—H11C108.9
C3—C2—C12120.4 (8)C12—C11B—H11D108.9
C1—C2—C12122.9 (6)C10—C11B—H11D108.9
C4—C3—C2123.5 (8)H11C—C11B—H11D107.7
C4—C3—H3118.3C2—C12—C11A112.3 (9)
C2—C3—H3118.3C2—C12—C11B109.9 (10)
C5—C4—C3120.2 (7)C2—C12—H12A109.1
C5—C4—H4119.9C11A—C12—H12A109.1
C3—C4—H4119.9C11B—C12—H12A68.9
C4—C5—C6119.7 (7)C2—C12—H12B109.1
C4—C5—H5120.1C11A—C12—H12B109.1
C6—C5—H5120.1C11B—C12—H12B139.4
C1—C6—C5119.7 (7)H12A—C12—H12B107.9
C1—C6—C7119.5 (6)C2—C12—H12C109.7
C5—C6—C7120.7 (7)C11A—C12—H12C136.4
O2—C7—C8126.0 (7)C11B—C12—H12C109.7
O2—C7—C6115.3 (6)H12B—C12—H12C66.2
C8—C7—C6118.7 (7)C2—C12—H12D109.7
C7—C8—C9118.7 (7)C11A—C12—H12D67.7
C7—C8—C13124.5 (7)C11B—C12—H12D109.7
C9—C8—C13116.7 (7)H12A—C12—H12D138.7
O1—C9—N1116.0 (7)H12B—C12—H12D45.0
O1—C9—C8121.3 (8)H12C—C12—H12D108.2
N1—C9—C8122.6 (6)O3—C13—O4125.5 (8)
N1—C10—C11A111.1 (8)O3—C13—C8120.9 (9)
N1—C10—C11B109.7 (9)O4—C13—C8113.6 (7)
N1—C10—H10A109.4O4—C14—C15106.3 (8)
C11A—C10—H10A109.4O4—C14—H14A110.5
C11B—C10—H10A139.2C15—C14—H14A110.5
N1—C10—H10B109.4O4—C14—H14B110.5
C11A—C10—H10B109.4C15—C14—H14B110.5
C11B—C10—H10B68.8H14A—C14—H14B108.7
H10A—C10—H10B108.0C14—C15—H15A109.5
N1—C10—H10C109.7C14—C15—H15B109.5
C11A—C10—H10C68.1H15A—C15—H15B109.5
C11B—C10—H10C109.7C14—C15—H15C109.5
H10B—C10—H10C138.4H15A—C15—H15C109.5
N1—C10—H10D109.7H15B—C15—H15C109.5
C11A—C10—H10D137.5
C9—N1—C1—C60.6 (8)C10—N1—C9—C8−179.9 (6)
C10—N1—C1—C6179.4 (5)C7—C8—C9—O1178.7 (6)
C9—N1—C1—C2−179.1 (6)C13—C8—C9—O1−4.2 (9)
C10—N1—C1—C2−0.3 (9)C7—C8—C9—N1−0.2 (9)
C6—C1—C2—C31.5 (9)C13—C8—C9—N1176.9 (6)
N1—C1—C2—C3−178.8 (6)C9—N1—C10—C11A155.4 (8)
C6—C1—C2—C12−177.9 (7)C1—N1—C10—C11A−23.5 (10)
N1—C1—C2—C121.8 (10)C9—N1—C10—C11B−157.4 (8)
C1—C2—C3—C4−3.0 (12)C1—N1—C10—C11B23.7 (10)
C12—C2—C3—C4176.4 (7)N1—C10—C11A—C1245.2 (15)
C2—C3—C4—C54.4 (13)C11B—C10—C11A—C12−51.8 (8)
C3—C4—C5—C6−4.0 (11)N1—C10—C11B—C12−48.6 (16)
N1—C1—C6—C5178.9 (5)C11A—C10—C11B—C1251.8 (8)
C2—C1—C6—C5−1.4 (9)C3—C2—C12—C11A−158.5 (10)
N1—C1—C6—C71.0 (8)C1—C2—C12—C11A20.9 (12)
C2—C1—C6—C7−179.3 (6)C3—C2—C12—C11B154.1 (9)
C4—C5—C6—C12.6 (10)C1—C2—C12—C11B−26.5 (11)
C4—C5—C6—C7−179.5 (7)C10—C11A—C12—C2−44.3 (16)
C1—C6—C7—O2178.5 (5)C10—C11A—C12—C11B51.8 (8)
C5—C6—C7—O20.6 (9)C10—C11B—C12—C250.2 (17)
C1—C6—C7—C8−2.2 (8)C10—C11B—C12—C11A−51.8 (8)
C5—C6—C7—C8179.9 (6)C14—O4—C13—O3−3.2 (11)
O2—C7—C8—C9−179.0 (6)C14—O4—C13—C8175.7 (6)
C6—C7—C8—C91.8 (9)C7—C8—C13—O3178.0 (7)
O2—C7—C8—C134.1 (11)C9—C8—C13—O31.0 (10)
C6—C7—C8—C13−175.1 (6)C7—C8—C13—O4−1.0 (10)
C1—N1—C9—O1180.0 (5)C9—C8—C13—O4−177.9 (6)
C10—N1—C9—O11.1 (8)C13—O4—C14—C15−155.4 (8)
C1—N1—C9—C8−1.0 (8)
D—H···AD—HH···AD···AD—H···A
O2—H2···O40.821.932.631 (7)142
O1—H1···O30.821.732.459 (10)147
C3—H3···Br1iii0.932.903.810 (9)168
C4—H4···Br2iv0.933.063.846 (9)143
C10—H10B···Br20.972.993.936 (8)166
C10—H10C···Br4ii0.972.923.752 (8)144
C11A—H11B···Br4ii0.973.023.797 (17)138
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
O2—H2⋯O40.821.932.631 (7)142
O1—H1⋯O30.821.732.459 (10)147
C3—H3⋯Br1i 0.932.903.810 (9)168
C4—H4⋯Br2ii 0.933.063.846 (9)143
C10—H10B⋯Br20.972.993.936 (8)166
C10—H10C⋯Br4iii 0.972.923.752 (8)144
C11A—H11B⋯Br4iii 0.973.023.797 (17)138

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

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1.  A short history of SHELX.

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Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290
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