Literature DB >> 22589911

rac-18-Meth-oxy-coronaridine hydro-chloride.

Martin E Kuehne1, Rory Waterman.   

Abstract

In the crystal structure of the racemic title compound, C(22)H(29)N(2)O(3) (+)·Cl(-), both NH groups form N-H⋯Cl hydrogen bonds with the chloride counter-ion, forming translational chains along the a axis.

Entities:  

Year:  2012        PMID： 22589911      PMCID： PMC3344002          DOI： 10.1107/S1600536812009981

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


Related literature

The title compound is a prospective anti-addictive and anti­leishmaniasis agent. For the synsthesis of the free base along with some bio-activity studies, see: Bandarage et al. (1995 ▶). For a study of related systems, see: Kuehne et al. (2003 ▶).

Experimental

Crystal data

C22H29N2O3 +·Cl− M = 404.92 Monoclinic, a = 9.3692 (14) Å b = 20.161 (3) Å c = 11.6281 (18) Å β = 110.221 (2)° V = 2061.1 (5) Å3 Z = 4 Mo Kα radiation μ = 0.21 mm−1 T = 125 K 0.21 × 0.17 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.958, T max = 0.983 22802 measured reflections 4374 independent reflections 2620 reflections with I > 2σ(I) R int = 0.100

Refinement

R[F 2 > 2σ(F 2)] = 0.053 wR(F 2) = 0.118 S = 1.01 4374 reflections 261 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.31 e Å−3 Δρmin = −0.32 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812009981/ld2049sup1.cif Supplementary material file. DOI: 10.1107/S1600536812009981/ld2049Isup2.cdx Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009981/ld2049Isup3.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C22H29N2O3+·Cl−F(000) = 864
Mr = 404.92Dx = 1.305 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4279 reflections
a = 9.3692 (14) Åθ = 2.5–26.9°
b = 20.161 (3) ŵ = 0.21 mm−1
c = 11.6281 (18) ÅT = 125 K
β = 110.221 (2)°Plate, colourless
V = 2061.1 (5) Å30.21 × 0.17 × 0.08 mm
Z = 4
Bruker APEXII CCD diffractometer4374 independent reflections
Radiation source: fine-focus sealed tube2620 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.100
φ and ω scansθmax = 26.7°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2007)h = −11→11
Tmin = 0.958, Tmax = 0.983k = −25→25
22802 measured reflectionsl = −14→14
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) = 0.118H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.0445P)2 + 0.8261P] where P = (Fo2 + 2Fc2)/3
4374 reflections(Δ/σ)max < 0.001
261 parametersΔρmax = 0.31 e Å−3
0 restraintsΔρmin = −0.32 e Å−3
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. Suitable crystals were mounted in a nylon loop with Paratone-N cryoprotectant oil and data collected on a Bruker APEX 2 CCD platform diffractometer. The structure was solved using direct methods and standard difference map techniques, and was refined by full-matrix least-squares procedures on F2 with SHELXTL Version 6.14 (Sheldrick, 2008).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
C2−0.6298 (3)−0.03049 (13)0.2437 (2)0.0159 (6)
C3−0.3327 (3)0.04266 (13)0.4114 (2)0.0204 (6)
H11A−0.23180.05090.47450.024*
H11B−0.38740.00990.44410.024*
C5−0.2795 (3)−0.05676 (13)0.2987 (2)0.0195 (6)
H10A−0.1936−0.06320.26870.023*
H10B−0.2456−0.07200.38490.023*
C6−0.4102 (3)−0.10020 (13)0.2237 (2)0.0194 (6)
H12C−0.4299−0.09180.13570.023*
H12D−0.3796−0.14720.24020.023*
C7−0.5551 (3)−0.08957 (13)0.2490 (2)0.0178 (6)
C8−0.6388 (3)−0.13907 (13)0.2870 (2)0.0177 (6)
C9−0.6179 (3)−0.20695 (13)0.3122 (2)0.0224 (6)
H12A−0.5347−0.22980.30150.027*
C10−0.7204 (3)−0.24016 (14)0.3529 (3)0.0268 (7)
H12B−0.7063−0.28610.37140.032*
C11−0.8452 (3)−0.20713 (14)0.3674 (2)0.0249 (7)
H11E−0.9144−0.23130.39490.030*
C12−0.8691 (3)−0.14076 (13)0.3427 (2)0.0204 (6)
H18A−0.9534−0.11860.35280.024*
C13−0.7655 (3)−0.10689 (13)0.3021 (2)0.0179 (6)
C14−0.4234 (3)0.10731 (13)0.3792 (2)0.0180 (6)
H10C−0.41450.13230.45570.022*
C15−0.3613 (3)0.14888 (13)0.2976 (2)0.0198 (6)
H19A−0.24910.15180.33430.024*
H19B−0.40340.19440.28980.024*
C16−0.5960 (3)0.03842 (12)0.2080 (2)0.0152 (6)
C17−0.5909 (3)0.09052 (13)0.3084 (2)0.0178 (6)
H11C−0.64680.13100.26990.021*
H11D−0.63930.07220.36490.021*
C18−0.2695 (3)0.19660 (14)0.0775 (3)0.0237 (6)
H11H−0.23840.22290.15410.028*
H11I−0.18820.20000.04150.028*
C19−0.2917 (3)0.12482 (13)0.1052 (2)0.0212 (6)
H11F−0.19270.10620.15750.025*
H11G−0.32580.09950.02750.025*
C20−0.4076 (3)0.11564 (12)0.1697 (2)0.0170 (6)
H18B−0.50470.13680.11700.020*
C21−0.4422 (3)0.04253 (13)0.1856 (2)0.0172 (6)
H17A−0.44780.01670.11080.021*
C22−0.7202 (3)0.05207 (13)0.0837 (2)0.0165 (6)
C98−0.9699 (3)0.08902 (16)−0.0188 (3)0.0345 (8)
H12E−1.05600.1086−0.00150.052*
H12F−1.00040.0462−0.06000.052*
H12G−0.93810.1189−0.07190.052*
C99−0.3917 (4)0.28863 (14)−0.0384 (3)0.0377 (8)
H11J−0.48890.3044−0.09630.057*
H11K−0.31360.2912−0.07660.057*
H11L−0.36170.31640.03540.057*
N1−0.7580 (2)−0.04105 (11)0.27505 (19)0.0167 (5)
N4−0.3142 (2)0.01673 (11)0.29607 (19)0.0174 (5)
H4−0.214 (4)0.0360 (15)0.299 (3)0.048 (10)*
O1−0.4075 (2)0.22182 (9)−0.00591 (17)0.0262 (5)
O2−0.7097 (2)0.03754 (9)−0.01348 (16)0.0256 (5)
O3−0.84383 (19)0.07907 (9)0.09564 (16)0.0246 (5)
Cl0.02001 (7)0.05216 (3)0.35272 (6)0.02537 (18)
H1−0.824 (3)−0.0090 (14)0.285 (2)0.027 (8)*
U11U22U33U12U13U23
C20.0138 (13)0.0207 (15)0.0116 (12)−0.0009 (11)0.0022 (10)0.0002 (11)
C30.0189 (14)0.0267 (16)0.0138 (13)0.0020 (12)0.0034 (11)−0.0005 (11)
C50.0169 (14)0.0194 (15)0.0208 (14)0.0057 (12)0.0049 (11)0.0016 (12)
C60.0181 (14)0.0185 (15)0.0218 (14)0.0031 (11)0.0070 (11)−0.0004 (12)
C70.0169 (14)0.0206 (15)0.0143 (13)0.0019 (11)0.0032 (11)−0.0017 (11)
C80.0166 (14)0.0199 (15)0.0132 (13)−0.0003 (11)0.0011 (11)−0.0018 (11)
C90.0188 (15)0.0226 (16)0.0223 (15)0.0011 (12)0.0027 (12)−0.0009 (12)
C100.0295 (17)0.0168 (15)0.0300 (17)−0.0018 (12)0.0052 (13)0.0031 (13)
C110.0215 (15)0.0263 (17)0.0246 (16)−0.0081 (12)0.0051 (13)0.0018 (12)
C120.0133 (14)0.0265 (16)0.0192 (14)−0.0028 (11)0.0030 (11)0.0002 (12)
C130.0152 (14)0.0218 (15)0.0135 (13)−0.0018 (11)0.0009 (11)−0.0001 (11)
C140.0174 (13)0.0205 (15)0.0147 (13)0.0023 (11)0.0039 (11)−0.0026 (11)
C150.0162 (14)0.0202 (15)0.0209 (14)−0.0022 (11)0.0038 (11)−0.0034 (12)
C160.0108 (13)0.0189 (15)0.0140 (13)0.0011 (10)0.0018 (10)0.0008 (11)
C170.0170 (14)0.0197 (15)0.0170 (14)0.0015 (11)0.0062 (11)−0.0001 (11)
C180.0190 (15)0.0273 (16)0.0254 (15)−0.0024 (12)0.0085 (12)0.0014 (13)
C190.0179 (14)0.0253 (16)0.0204 (15)0.0014 (12)0.0065 (12)0.0016 (12)
C200.0141 (13)0.0195 (15)0.0159 (13)0.0011 (11)0.0035 (11)0.0024 (11)
C210.0134 (13)0.0230 (16)0.0133 (13)0.0013 (11)0.0021 (10)−0.0004 (11)
C220.0151 (13)0.0151 (14)0.0192 (14)−0.0010 (11)0.0059 (11)0.0007 (11)
C980.0188 (16)0.052 (2)0.0237 (16)0.0125 (14)−0.0035 (13)−0.0020 (15)
C990.051 (2)0.0228 (18)0.044 (2)0.0058 (15)0.0223 (17)0.0096 (15)
N10.0133 (11)0.0181 (13)0.0187 (12)0.0011 (9)0.0052 (9)−0.0012 (9)
N40.0141 (12)0.0219 (13)0.0135 (11)0.0006 (9)0.0013 (9)0.0005 (9)
O10.0247 (11)0.0212 (11)0.0329 (12)0.0015 (8)0.0103 (9)0.0061 (9)
O20.0212 (10)0.0398 (13)0.0148 (10)0.0043 (9)0.0049 (8)−0.0033 (9)
O30.0162 (10)0.0372 (12)0.0175 (10)0.0087 (8)0.0019 (8)−0.0009 (8)
Cl0.0161 (3)0.0283 (4)0.0299 (4)0.0018 (3)0.0056 (3)−0.0024 (3)
C2—C71.372 (4)C15—H19B0.9900
C2—N11.387 (3)C16—C221.535 (3)
C2—C161.514 (3)C16—C211.552 (3)
C3—N41.504 (3)C16—C171.559 (3)
C3—C141.530 (3)C17—H11C0.9900
C3—H11A0.9900C17—H11D0.9900
C3—H11B0.9900C18—O11.416 (3)
C5—C61.513 (3)C18—C191.512 (4)
C5—N41.515 (3)C18—H11H0.9900
C5—H10A0.9900C18—H11I0.9900
C5—H10B0.9900C19—C201.530 (3)
C6—C71.500 (3)C19—H11F0.9900
C6—H12C0.9900C19—H11G0.9900
C6—H12D0.9900C20—C211.534 (4)
C7—C81.430 (4)C20—H18B1.0000
C8—C91.399 (4)C21—N41.515 (3)
C8—C131.416 (4)C21—H17A1.0000
C9—C101.381 (4)C22—O21.204 (3)
C9—H12A0.9500C22—O31.330 (3)
C10—C111.406 (4)C98—O31.456 (3)
C10—H12B0.9500C98—H12E0.9800
C11—C121.371 (4)C98—H12F0.9800
C11—H11E0.9500C98—H12G0.9800
C12—C131.396 (4)C99—O11.420 (3)
C12—H18A0.9500C99—H11J0.9800
C13—N11.372 (3)C99—H11K0.9800
C14—C151.524 (4)C99—H11L0.9800
C14—C171.537 (3)N1—H10.93 (3)
C14—H10C1.0000N4—Cl3.054 (2)
C15—C201.550 (3)N4—H41.01 (3)
C15—H19A0.9900
C7—C2—N1109.2 (2)C14—C17—C16108.1 (2)
C7—C2—C16131.0 (2)C14—C17—H11C110.1
N1—C2—C16119.7 (2)C16—C17—H11C110.1
N4—C3—C14107.7 (2)C14—C17—H11D110.1
N4—C3—H11A110.2C16—C17—H11D110.1
C14—C3—H11A110.2H11C—C17—H11D108.4
N4—C3—H11B110.2O1—C18—C19109.2 (2)
C14—C3—H11B110.2O1—C18—H11H109.8
H11A—C3—H11B108.5C19—C18—H11H109.8
C6—C5—N4115.4 (2)O1—C18—H11I109.8
C6—C5—H10A108.4C19—C18—H11I109.8
N4—C5—H10A108.4H11H—C18—H11I108.3
C6—C5—H10B108.4C18—C19—C20113.2 (2)
N4—C5—H10B108.4C18—C19—H11F108.9
H10A—C5—H10B107.5C20—C19—H11F108.9
C7—C6—C5114.3 (2)C18—C19—H11G108.9
C7—C6—H12C108.7C20—C19—H11G108.9
C5—C6—H12C108.7H11F—C19—H11G107.8
C7—C6—H12D108.7C19—C20—C21113.0 (2)
C5—C6—H12D108.7C19—C20—C15114.1 (2)
H12C—C6—H12D107.6C21—C20—C15107.5 (2)
C2—C7—C8107.1 (2)C19—C20—H18B107.3
C2—C7—C6126.7 (2)C21—C20—H18B107.3
C8—C7—C6126.2 (2)C15—C20—H18B107.3
C9—C8—C13119.0 (2)N4—C21—C20107.1 (2)
C9—C8—C7134.0 (2)N4—C21—C16110.39 (19)
C13—C8—C7106.9 (2)C20—C21—C16108.6 (2)
C10—C9—C8118.8 (3)N4—C21—H17A110.2
C10—C9—H12A120.6C20—C21—H17A110.2
C8—C9—H12A120.6C16—C21—H17A110.2
C9—C10—C11121.1 (3)O2—C22—O3123.7 (2)
C9—C10—H12B119.4O2—C22—C16124.0 (2)
C11—C10—H12B119.4O3—C22—C16112.3 (2)
C12—C11—C10121.3 (3)O3—C98—H12E109.5
C12—C11—H11E119.3O3—C98—H12F109.5
C10—C11—H11E119.3H12E—C98—H12F109.5
C11—C12—C13117.8 (3)O3—C98—H12G109.5
C11—C12—H18A121.1H12E—C98—H12G109.5
C13—C12—H18A121.1H12F—C98—H12G109.5
N1—C13—C12130.4 (2)O1—C99—H11J109.5
N1—C13—C8107.7 (2)O1—C99—H11K109.5
C12—C13—C8121.9 (2)H11J—C99—H11K109.5
C15—C14—C3108.7 (2)O1—C99—H11L109.5
C15—C14—C17109.0 (2)H11J—C99—H11L109.5
C3—C14—C17108.8 (2)H11K—C99—H11L109.5
C15—C14—H10C110.1C13—N1—C2109.0 (2)
C3—C14—H10C110.1C13—N1—H1123.8 (17)
C17—C14—H10C110.1C2—N1—H1126.9 (17)
C14—C15—C20108.6 (2)C3—N4—C21109.59 (19)
C14—C15—H19A110.0C3—N4—C5114.3 (2)
C20—C15—H19A110.0C21—N4—C5117.03 (19)
C14—C15—H19B110.0C3—N4—Cl98.72 (14)
C20—C15—H19B110.0C21—N4—Cl123.72 (15)
H19A—C15—H19B108.3C5—N4—Cl91.58 (13)
C2—C16—C22105.1 (2)C3—N4—H4103.3 (18)
C2—C16—C21112.9 (2)C21—N4—H4110.6 (18)
C22—C16—C21106.13 (19)C5—N4—H4100.7 (18)
C2—C16—C17111.6 (2)Cl—N4—H413.3 (18)
C22—C16—C17113.6 (2)C18—O1—C99111.6 (2)
C21—C16—C17107.45 (19)C22—O3—C98114.9 (2)
N4—C5—C6—C7−51.3 (3)C18—C19—C20—C15−62.8 (3)
N1—C2—C7—C8−0.9 (3)C14—C15—C20—C19−147.6 (2)
C16—C2—C7—C8−179.2 (2)C14—C15—C20—C21−21.4 (3)
N1—C2—C7—C6−179.1 (2)C19—C20—C21—N480.5 (2)
C16—C2—C7—C62.7 (4)C15—C20—C21—N4−46.3 (3)
C5—C6—C7—C254.5 (4)C19—C20—C21—C16−160.3 (2)
C5—C6—C7—C8−123.3 (3)C15—C20—C21—C1672.9 (2)
C2—C7—C8—C9−177.7 (3)C2—C16—C21—N4−54.3 (3)
C6—C7—C8—C90.4 (5)C22—C16—C21—N4−168.9 (2)
C2—C7—C8—C130.7 (3)C17—C16—C21—N469.2 (2)
C6—C7—C8—C13178.9 (2)C2—C16—C21—C20−171.4 (2)
C13—C8—C9—C10−1.0 (4)C22—C16—C21—C2074.0 (2)
C7—C8—C9—C10177.3 (3)C17—C16—C21—C20−47.9 (2)
C8—C9—C10—C110.9 (4)C2—C16—C22—O2−88.7 (3)
C9—C10—C11—C12−0.5 (4)C21—C16—C22—O231.2 (3)
C10—C11—C12—C130.2 (4)C17—C16—C22—O2149.1 (3)
C11—C12—C13—N1−177.4 (2)C2—C16—C22—O388.4 (2)
C11—C12—C13—C8−0.3 (4)C21—C16—C22—O3−151.7 (2)
C9—C8—C13—N1178.4 (2)C17—C16—C22—O3−33.8 (3)
C7—C8—C13—N1−0.3 (3)C12—C13—N1—C2177.2 (3)
C9—C8—C13—C120.8 (4)C8—C13—N1—C2−0.2 (3)
C7—C8—C13—C12−178.0 (2)C7—C2—N1—C130.7 (3)
N4—C3—C14—C15−44.1 (3)C16—C2—N1—C13179.2 (2)
N4—C3—C14—C1774.5 (2)C14—C3—N4—C21−25.3 (3)
C3—C14—C15—C2071.2 (3)C14—C3—N4—C5−158.9 (2)
C17—C14—C15—C20−47.2 (3)C14—C3—N4—Cl105.34 (18)
C7—C2—C16—C22108.9 (3)C20—C21—N4—C375.1 (2)
N1—C2—C16—C22−69.2 (3)C16—C21—N4—C3−42.9 (3)
C7—C2—C16—C21−6.4 (4)C20—C21—N4—C5−152.6 (2)
N1—C2—C16—C21175.5 (2)C16—C21—N4—C589.4 (2)
C7—C2—C16—C17−127.5 (3)C20—C21—N4—Cl−40.4 (2)
N1—C2—C16—C1754.4 (3)C16—C21—N4—Cl−158.41 (15)
C15—C14—C17—C1672.0 (3)C6—C5—N4—C3105.4 (2)
C3—C14—C17—C16−46.4 (3)C6—C5—N4—C21−24.7 (3)
C2—C16—C17—C14103.9 (2)C6—C5—N4—Cl−154.30 (19)
C22—C16—C17—C14−137.5 (2)C19—C18—O1—C99−178.0 (2)
C21—C16—C17—C14−20.4 (3)O2—C22—O3—C981.2 (4)
O1—C18—C19—C20−63.6 (3)C16—C22—O3—C98−175.9 (2)
C18—C19—C20—C21174.0 (2)
D—H···AD—HH···AD···AD—H···A
N4—H4···Cl1.01 (3)2.09 (3)3.054 (2)160 (3)
N1—H1···Cli0.93 (3)2.25 (3)3.157 (2)165 (2)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N4—H4⋯Cl1.01 (3)2.09 (3)3.054 (2)160 (3)
N1—H1⋯Cli0.93 (3)2.25 (3)3.157 (2)165 (2)

Symmetry code: (i) .

  2 in total

1.  Synthesis and biological evaluation of 18-methoxycoronaridine congeners. Potential antiaddiction agents.

Authors:  Martin E Kuehne; Liwen He; Patrick A Jokiel; C J Pace; M W Fleck; I M Maisonneuve; Stanley D Glick; Jean M Bidlack
Journal:  J Med Chem       Date:  2003-06-19       Impact factor: 7.446

2.  A short history of SHELX.

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

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