Buy article online - an online subscription or single-article purchase is required to access this article.
share
share
Issue contentsclose
Statistics
close
Download citation
closeDownload citation
Format BIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Text
Plain Text
Download PDF of article
Download PDF of articleclose
Acta Cryst. (2004). B60, 481-489
https://doi.org/10.1107/S0108768104013564
Download PDF of article
Download PDF of articleclose
Download citation
closeDownload citation
Format BIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Text
Plain Text
Statistics
close
Issue contentsclose
share
link to html

Structural features controlling the binding of β-carbolines to the benzodiazepine receptor

V. Ferretti, P. Gilli and P. A. Borea
β-Carbolines are a class of drug which can interact with a high affinity with the benzodiazepine (BDZ) binding site of the GABAA receptor. The present paper, aimed at obtaining a deeper insight into the structure–properties relationships of this class of molecules, reports the crystal structures of four β-carbolines: ZK93423 (3-carboethoxy-4-methoxymethyl-6-benzyloxy-β-carboline), ZK91296 (3-carboethoxy-4-methoxymethyl-5-benzyloxy-β-carboline), FG7142 (N-methyl-3-carbamoyl-β-carboline) and the low-affinity ligand harmine hydrochloride (1-methyl-7-methoxy-β-carboline). This set of structural data is completed by the X-ray structures of other carbolines of known biological activity retrieved from the Cambridge Crystallographic Database and by the structures of β-CCE (3-carboethoxy-β-carboline), 6-PBC (3-carboethoxy-4-methoxymethyl-6-isopropoxy-β-carboline), PRCC (3-isopropoxy-β-carboline) and ZK93426 (3-carboethoxy-4-methyl-5-isopropoxy-β-carboline), which have been obtained by molecular-mechanics simulations. The structural features of all these molecules have been compared according to the stereochemical model we proposed in 1987. The structural comparison is integrated by the Free–Wilson analysis on 32 β-carbolines of known binding affinity data.
Keywords: benzodiazepine; receptor agonists and antagonists; β-carbolines; binding affinity data.
Read articleSimilar articles

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768104013564/na5019sup1.cif
Contains datablocks ZK93423, ZK91296, FG7142, Harmine

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768104013564/na5019ZK93423sup2.hkl
Contains datablock shelxl

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768104013564/na5019ZK91296sup3.hkl
Contains datablock shelxl

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768104013564/na5019FG7142sup4.hkl
Contains datablock shelxl

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768104013564/na5019Harminesup5.hkl
Contains datablock shelxl

CCDC references: 224354; 224355; 224356; 224357

Computing details top

For all compounds, data collection: Kappa CCD server software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ORTEP (Burnett & Johnson, 1996) for ZK93423, ZK91296; ORTEP(Burnett & Johnson, 1996) for FG7142, Harmine. For all compounds, software used to prepare material for publication: SHELXL97 (Sheldrick, 1997); PARST (Nardelli, 1983, 1995); PLATON (Spek, 1998).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
(ZK93423) 3-carboethoxy-6-benzyloxy-4-methoxymethyl-beta carboline top
Crystal data top
C23H22N2O4F(000) = 412
Mr = 390.43Dx = 1.346 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71070 Å
a = 5.0472 (2) ÅCell parameters from 4907 reflections
b = 11.3381 (5) Åθ = 1.0–29.0°
c = 16.8796 (7) ŵ = 0.09 mm−1
β = 94.331 (3)°T = 100 K
V = 963.19 (7) Å3Prism, colourless
Z = 20.5 × 0.24 × 0.07 mm
Data collection top
Nonius Kappa CCD
diffractometer		2316 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.034
Graphite monochromatorθmax = 29.0°, θmin = 2.2°
ϕ scans and ω scansh = −6→6
4907 measured reflectionsk = −15→15
2664 independent reflectionsl = −22→22
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043All H-atom parameters refined
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0457P)2 + 0.304P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.004
2664 reflectionsΔρmax = 0.38 e Å−3
349 parametersΔρmin = −0.28 e Å−3
0 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 1.4 (13)
Crystal data top
C23H22N2O4V = 963.19 (7) Å3
Mr = 390.43Z = 2
Monoclinic, P21Mo Kα radiation
a = 5.0472 (2) ŵ = 0.09 mm−1
b = 11.3381 (5) ÅT = 100 K
c = 16.8796 (7) Å0.5 × 0.24 × 0.07 mm
β = 94.331 (3)°
Data collection top
Nonius Kappa CCD
diffractometer		2316 reflections with I > 2σ(I)
4907 measured reflectionsRint = 0.034
2664 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.043All H-atom parameters refined
wR(F2) = 0.103Δρmax = 0.38 e Å−3
S = 1.08Δρmin = −0.28 e Å−3
2664 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
349 parametersAbsolute structure parameter: 1.4 (13)
0 restraints
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*/Ueq
O1−0.1031 (3)0.7409 (2)0.26122 (10)0.0210 (4)
O20.4828 (4)1.11500.19851 (10)0.0235 (4)
O30.9394 (4)1.4086 (2)0.38119 (11)0.0319 (5)
O40.8350 (4)1.3334 (2)0.25931 (10)0.0254 (4)
N11.0054 (4)1.1769 (3)0.43059 (12)0.0180 (4)
N20.7541 (4)0.8767 (3)0.46196 (13)0.0188 (4)
C10.8281 (5)1.2047 (3)0.36871 (14)0.0181 (5)
C20.6306 (5)1.1291 (3)0.33641 (14)0.0162 (5)
C30.6206 (4)1.0167 (3)0.37067 (13)0.0158 (5)
C40.4513 (5)0.9146 (3)0.35761 (14)0.0164 (5)
C50.2362 (5)0.8874 (3)0.30209 (15)0.0178 (5)
C60.1159 (5)0.7789 (3)0.30878 (14)0.0185 (5)
C70.2048 (5)0.6973 (3)0.36779 (15)0.0202 (5)
C80.4170 (5)0.7217 (3)0.42133 (15)0.0203 (5)
C90.5412 (5)0.8313 (3)0.41544 (13)0.0181 (5)
C100.8052 (5)0.9883 (3)0.43548 (14)0.0176 (5)
C110.9959 (5)1.0703 (3)0.46258 (15)0.0190 (5)
C12−0.2122 (5)0.8193 (3)0.20094 (15)0.0203 (5)
C13−0.0647 (5)0.8172 (3)0.12630 (14)0.0196 (5)
C14−0.1115 (6)0.9058 (3)0.07056 (16)0.0291 (6)
C150.0151 (7)0.9041 (4)−0.00010 (19)0.0362 (7)
C160.1887 (6)0.8128 (4)−0.01486 (16)0.0302 (6)
C170.2357 (5)0.7243 (3)0.04060 (16)0.0272 (6)
C180.1080 (5)0.7260 (3)0.11098 (16)0.0227 (5)
C190.4212 (5)1.1645 (3)0.27290 (15)0.0180 (5)
C200.2876 (6)1.1509 (4)0.13794 (18)0.0318 (7)
C210.8699 (5)1.3273 (3)0.33899 (14)0.0190 (5)
C220.8614 (6)1.4488 (3)0.22317 (17)0.0271 (6)
C230.5934 (7)1.5017 (3)0.2027 (3)0.0398 (8)
H1N0.848 (6)0.846 (3)0.5006 (19)0.026 (8)*
H10.170 (5)0.944 (3)0.2598 (17)0.016 (7)*
H20.115 (6)0.627 (3)0.3710 (19)0.030 (9)*
H30.472 (6)0.670 (4)0.4597 (19)0.030 (9)*
H41.123 (7)1.056 (3)0.507 (2)0.032 (9)*
H5−0.395 (5)0.795 (3)0.1921 (15)0.010 (6)*
H6−0.226 (6)0.896 (3)0.2221 (18)0.024 (8)*
H70.281 (6)0.811 (3)−0.0642 (18)0.027 (8)*
H80.355 (6)0.664 (3)0.0290 (18)0.026 (8)*
H90.142 (6)0.665 (4)0.1498 (19)0.027 (8)*
H100.245 (5)1.133 (3)0.2845 (14)0.008 (6)*
H110.110 (7)1.134 (3)0.1535 (18)0.023 (8)*
H120.329 (7)1.104 (4)0.090 (2)0.037 (9)*
H130.288 (7)1.244 (4)0.132 (2)0.033 (9)*
H140.993 (7)1.499 (3)0.2609 (19)0.031 (9)*
H150.964 (7)1.434 (4)0.169 (2)0.041 (10)*
H160.603 (8)1.584 (5)0.169 (3)0.056 (12)*
H170.486 (9)1.448 (5)0.166 (3)0.060 (13)*
H180.517 (9)1.520 (5)0.251 (3)0.056 (12)*
H190.401 (6)1.256 (3)0.2692 (18)0.022 (8)*
H20−0.235 (7)0.969 (4)0.082 (2)0.038 (10)*
H21−0.017 (7)0.964 (4)−0.042 (2)0.046 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0221 (8)0.0189 (9)0.0216 (9)−0.0057 (7)−0.0008 (7)0.0004 (7)
O20.0253 (9)0.0279 (10)0.0169 (8)0.0016 (8)−0.0013 (7)0.0000 (7)
O30.0524 (13)0.0169 (9)0.0255 (10)−0.0085 (9)−0.0033 (9)−0.0017 (8)
O40.0363 (10)0.0167 (9)0.0223 (9)−0.0056 (8)−0.0027 (7)0.0016 (8)
N10.0192 (9)0.0174 (10)0.0175 (10)−0.0006 (8)0.0007 (7)−0.0012 (8)
N20.0224 (10)0.0139 (10)0.0195 (10)0.0009 (8)−0.0018 (8)0.0016 (8)
C10.0190 (11)0.0157 (12)0.0197 (12)0.0007 (9)0.0021 (9)−0.0017 (9)
C20.0183 (11)0.0136 (11)0.0169 (11)0.0025 (9)0.0015 (8)0.0004 (9)
C30.0163 (10)0.0149 (11)0.0164 (11)0.0004 (9)0.0026 (8)−0.0019 (9)
C40.0179 (11)0.0127 (10)0.0189 (11)−0.0003 (9)0.0040 (8)−0.0024 (9)
C50.0189 (11)0.0155 (12)0.0190 (11)0.0000 (9)0.0023 (9)−0.0007 (9)
C60.0202 (11)0.0174 (12)0.0180 (11)−0.0018 (9)0.0029 (9)−0.0008 (9)
C70.0239 (12)0.0143 (12)0.0228 (12)−0.0030 (10)0.0052 (10)0.0002 (9)
C80.0246 (12)0.0146 (11)0.0219 (12)−0.0021 (10)0.0038 (9)0.0024 (10)
C90.0210 (11)0.0151 (11)0.0187 (11)0.0025 (10)0.0036 (9)−0.0009 (9)
C100.0208 (11)0.0146 (12)0.0174 (11)0.0015 (9)0.0017 (9)0.0001 (9)
C110.0189 (11)0.0201 (12)0.0179 (11)0.0017 (10)0.0004 (9)−0.0019 (9)
C120.0168 (11)0.0196 (12)0.0244 (12)−0.0024 (10)0.0013 (9)−0.0009 (10)
C130.0175 (11)0.0192 (12)0.0218 (11)−0.0041 (10)−0.0008 (9)−0.0023 (10)
C140.0338 (14)0.0264 (14)0.0273 (14)0.0072 (13)0.0024 (11)0.0028 (12)
C150.0488 (17)0.0367 (17)0.0231 (13)0.0069 (15)0.0027 (11)0.0053 (13)
C160.0321 (14)0.0363 (17)0.0228 (13)0.0004 (13)0.0058 (11)−0.0004 (12)
C170.0243 (12)0.0284 (14)0.0291 (13)0.0045 (12)0.0034 (10)−0.0037 (12)
C180.0225 (12)0.0200 (12)0.0254 (13)−0.0003 (11)0.0006 (9)−0.0006 (10)
C190.0170 (11)0.0161 (12)0.0205 (11)0.0017 (9)−0.0004 (9)−0.0003 (9)
C200.0319 (15)0.0389 (18)0.0233 (14)−0.0004 (13)−0.0056 (11)0.0026 (13)
C210.0172 (11)0.0165 (12)0.0228 (11)−0.0006 (10)−0.0013 (9)0.0008 (10)
C220.0326 (14)0.0202 (13)0.0280 (14)−0.0063 (11)−0.0017 (11)0.0043 (11)
C230.0306 (15)0.0212 (15)0.066 (2)0.0005 (13)−0.0073 (16)0.0016 (16)
Geometric parameters (Å, º) top
O1—C61.385 (3)C10—C111.390 (4)
O1—C121.430 (3)C11—H40.96 (3)
O2—C201.425 (3)C12—C131.511 (3)
O2—C191.431 (3)C12—H50.96 (3)
O3—C211.201 (3)C12—H60.94 (4)
O4—C211.345 (3)C13—C141.385 (4)
O4—C221.454 (3)C13—C181.389 (4)
N1—C111.326 (3)C14—C151.395 (4)
N1—C11.360 (3)C14—H200.98 (4)
N2—C101.373 (3)C15—C161.391 (5)
N2—C91.382 (3)C15—H210.99 (4)
N2—H1N0.85 (3)C16—C171.380 (4)
C1—C21.395 (3)C16—H70.99 (3)
C1—C211.498 (4)C17—C181.394 (4)
C2—C31.402 (3)C17—H80.94 (4)
C2—C191.502 (3)C18—H90.96 (4)
C3—C101.419 (3)C19—H100.99 (3)
C3—C41.446 (3)C19—H191.04 (4)
C4—C91.409 (3)C20—H110.97 (3)
C4—C51.413 (3)C20—H121.00 (4)
C5—C61.380 (3)C20—H131.06 (4)
C5—H11.00 (3)C22—C231.496 (4)
C6—C71.408 (4)C22—H141.05 (3)
C7—C81.376 (4)C22—H151.10 (4)
C7—H20.92 (4)C23—H161.10 (5)
C8—C91.399 (4)C23—H171.00 (5)
C8—H30.90 (4)C23—H180.95 (4)
C6—O1—C12117.82 (19)C14—C13—C18119.4 (2)
C20—O2—C19109.5 (2)C14—C13—C12119.0 (2)
C21—O4—C22117.2 (2)C18—C13—C12121.5 (2)
C11—N1—C1118.8 (2)C13—C14—C15120.3 (3)
C10—N2—C9108.4 (2)C13—C14—H20118 (2)
C10—N2—H1N122 (2)C15—C14—H20122 (2)
C9—N2—H1N130 (2)C16—C15—C14119.9 (3)
N1—C1—C2124.6 (2)C16—C15—H21117 (2)
N1—C1—C21111.8 (2)C14—C15—H21123 (2)
C2—C1—C21123.7 (2)C17—C16—C15119.9 (3)
C1—C2—C3116.4 (2)C17—C16—H7119 (2)
C1—C2—C19123.9 (2)C15—C16—H7121 (2)
C3—C2—C19119.5 (2)C16—C17—C18120.1 (3)
C2—C3—C10118.8 (2)C16—C17—H8118 (2)
C2—C3—C4134.7 (2)C18—C17—H8122 (2)
C10—C3—C4106.4 (2)C13—C18—C17120.4 (3)
C9—C4—C5120.3 (2)C13—C18—H9119 (2)
C9—C4—C3106.0 (2)C17—C18—H9120 (2)
C5—C4—C3133.7 (2)O2—C19—C2109.50 (19)
C6—C5—C4117.4 (2)O2—C19—H10106.9 (15)
C6—C5—H1120.5 (17)C2—C19—H10111.0 (15)
C4—C5—H1122.0 (17)O2—C19—H19111.3 (17)
C5—C6—O1124.5 (2)C2—C19—H19111.7 (17)
C5—C6—C7121.7 (2)H10—C19—H19106 (2)
O1—C6—C7113.8 (2)O2—C20—H11110.7 (18)
C8—C7—C6121.5 (2)O2—C20—H12104 (2)
C8—C7—H2120 (2)H11—C20—H12112 (3)
C6—C7—H2119 (2)O2—C20—H13110.3 (19)
C7—C8—C9117.6 (2)H11—C20—H13103 (3)
C7—C8—H3122 (2)H12—C20—H13117 (3)
C9—C8—H3121 (2)O3—C21—O4124.3 (2)
N2—C9—C8128.6 (2)O3—C21—C1123.8 (2)
N2—C9—C4109.9 (2)O4—C21—C1111.8 (2)
C8—C9—C4121.5 (2)O4—C22—C23110.4 (2)
N2—C10—C11130.7 (2)O4—C22—H14108 (2)
N2—C10—C3109.3 (2)C23—C22—H14116 (2)
C11—C10—C3120.0 (2)O4—C22—H15106 (2)
N1—C11—C10121.4 (2)C23—C22—H15109.9 (19)
N1—C11—H4115 (2)H14—C22—H15106 (3)
C10—C11—H4123 (2)C22—C23—H16113 (2)
O1—C12—C13113.3 (2)C22—C23—H17110 (3)
O1—C12—H5104.2 (17)H16—C23—H17104 (3)
C13—C12—H5113.1 (15)C22—C23—H18108 (3)
O1—C12—H6109.8 (19)H16—C23—H18108 (4)
C13—C12—H6112.7 (19)H17—C23—H18115 (4)
H5—C12—H6103 (3)
(ZK91296) '3-carboxyethoxy-5-benzyloxy-4-methoxymethyl-beta-carboline' top
Crystal data top
C23H22N2O4Dx = 1.317 Mg m−3
Mr = 390.43Mo Kα radiation, λ = 0.71070 Å
Orthorhombic, P212121Cell parameters from 5595 reflections
a = 9.9033 (5) Åθ = 3.1–30.0°
b = 11.5758 (4) ŵ = 0.09 mm−1
c = 17.1805 (9) ÅT = 293 K
V = 1969.58 (16) Å3Plate, colourless
Z = 40.45 × 0.30 × 0.09 mm
F(000) = 824
Data collection top
Nonius Kappa CCD
diffractometer		2330 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
Graphite monochromatorθmax = 30.0°, θmin = 3.1°
ϕ scans and ω scansh = −13→13
5595 measured reflectionsk = −16→16
3201 independent reflectionsl = −23→23
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048All H-atom parameters refined
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.0406P)2 + 0.4347P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.073
3201 reflectionsΔρmax = 0.18 e Å−3
350 parametersΔρmin = −0.18 e Å−3
0 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: −1.7 (15)
Crystal data top
C23H22N2O4V = 1969.58 (16) Å3
Mr = 390.43Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 9.9033 (5) ŵ = 0.09 mm−1
b = 11.5758 (4) ÅT = 293 K
c = 17.1805 (9) Å0.45 × 0.30 × 0.09 mm
Data collection top
Nonius Kappa CCD
diffractometer		2330 reflections with I > 2σ(I)
5595 measured reflectionsRint = 0.033
3201 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.048All H-atom parameters refined
wR(F2) = 0.111Δρmax = 0.18 e Å−3
S = 1.04Δρmin = −0.18 e Å−3
3201 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
350 parametersAbsolute structure parameter: −1.7 (15)
0 restraints
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*/Ueq
O10.47842 (16)0.75732 (14)0.35101 (11)0.0408 (4)
O20.70324 (19)0.49689 (16)0.47152 (10)0.0483 (5)
O30.8647 (2)0.26958 (17)0.37739 (13)0.0602 (6)
O40.64550 (19)0.31526 (16)0.36932 (12)0.0503 (5)
N10.9046 (2)0.44967 (19)0.27257 (13)0.0428 (5)
N20.8746 (2)0.7498 (2)0.20710 (13)0.0450 (5)
C10.7994 (2)0.4525 (2)0.32280 (14)0.0364 (5)
C20.7210 (2)0.54982 (19)0.33888 (13)0.0340 (5)
C30.7449 (2)0.64796 (19)0.29271 (13)0.0331 (5)
C40.6883 (2)0.76357 (19)0.28454 (13)0.0346 (5)
C50.5691 (2)0.8198 (2)0.30828 (15)0.0376 (5)
C60.5469 (3)0.9340 (2)0.28550 (16)0.0443 (6)
C70.6394 (3)0.9903 (2)0.23692 (18)0.0516 (7)
C80.7518 (3)0.9373 (2)0.20880 (18)0.0509 (7)
C90.7746 (3)0.8229 (2)0.23228 (14)0.0413 (6)
C100.8583 (3)0.6442 (2)0.24248 (14)0.0380 (5)
C110.9358 (3)0.5458 (2)0.23444 (15)0.0442 (6)
C120.3528 (3)0.8122 (2)0.36990 (18)0.0449 (6)
C130.2656 (2)0.7270 (2)0.41178 (15)0.0400 (5)
C140.3126 (3)0.6728 (3)0.47812 (17)0.0528 (7)
C150.2316 (4)0.5952 (3)0.5184 (2)0.0672 (9)
C160.1020 (3)0.5743 (3)0.4921 (2)0.0636 (9)
C170.0536 (3)0.6292 (3)0.4271 (2)0.0573 (8)
C180.1353 (3)0.7051 (2)0.38679 (18)0.0472 (6)
C190.6321 (3)0.5536 (2)0.41037 (15)0.0399 (5)
C200.6209 (4)0.4791 (3)0.53777 (18)0.0577 (8)
C210.7761 (3)0.3374 (2)0.36055 (15)0.0413 (6)
C220.6087 (3)0.2114 (3)0.4120 (2)0.0569 (8)
C230.4587 (4)0.2088 (3)0.4161 (3)0.0695 (10)
H160.047 (4)0.517 (3)0.524 (2)0.080 (11)*
H140.408 (3)0.691 (3)0.4987 (19)0.069 (9)*
H150.273 (4)0.555 (3)0.568 (2)0.087 (12)*
H180.106 (3)0.739 (3)0.344 (2)0.064 (10)*
H60.461 (3)0.974 (3)0.3024 (18)0.059 (9)*
H70.620 (3)1.069 (3)0.2209 (18)0.063 (9)*
H20A0.538 (4)0.431 (3)0.520 (2)0.073 (10)*
H20.951 (3)0.765 (3)0.1802 (19)0.065 (9)*
H111.020 (3)0.540 (3)0.2030 (17)0.053 (8)*
H190.610 (3)0.639 (2)0.4284 (15)0.038 (7)*
H19A0.539 (3)0.513 (2)0.3997 (15)0.044 (7)*
H200.682 (4)0.437 (4)0.582 (3)0.105 (14)*
H20B0.586 (4)0.560 (4)0.557 (2)0.080 (11)*
H220.648 (4)0.144 (3)0.385 (2)0.075 (11)*
H22A0.657 (4)0.217 (3)0.464 (2)0.084 (12)*
H230.424 (4)0.276 (3)0.4368 (19)0.067 (11)*
H120.371 (3)0.885 (3)0.4037 (18)0.056 (8)*
H12A0.312 (3)0.836 (3)0.3212 (19)0.058 (9)*
H17−0.040 (4)0.616 (3)0.409 (2)0.069 (10)*
H23A0.431 (5)0.147 (4)0.451 (3)0.118 (16)*
H23B0.422 (5)0.187 (5)0.366 (3)0.13 (2)*
H80.814 (3)0.978 (3)0.1727 (18)0.063 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0350 (8)0.0320 (8)0.0554 (10)0.0015 (7)0.0068 (8)0.0077 (7)
O20.0478 (10)0.0550 (10)0.0421 (10)0.0087 (9)0.0058 (9)0.0113 (8)
O30.0506 (11)0.0506 (11)0.0794 (14)0.0169 (10)0.0128 (11)0.0168 (11)
O40.0421 (9)0.0369 (9)0.0720 (13)−0.0019 (9)−0.0010 (10)0.0135 (9)
N10.0383 (11)0.0440 (11)0.0461 (12)0.0026 (10)0.0055 (9)−0.0022 (9)
N20.0371 (11)0.0505 (12)0.0472 (12)−0.0093 (10)0.0080 (10)0.0113 (10)
C10.0332 (11)0.0369 (11)0.0391 (12)−0.0003 (10)−0.0002 (10)−0.0023 (10)
C20.0292 (10)0.0341 (10)0.0387 (12)−0.0024 (10)0.0003 (9)0.0008 (9)
C30.0279 (10)0.0360 (11)0.0355 (11)−0.0053 (9)−0.0017 (9)0.0023 (9)
C40.0329 (11)0.0321 (10)0.0389 (12)−0.0066 (9)−0.0046 (9)0.0040 (9)
C50.0362 (11)0.0318 (11)0.0450 (13)−0.0065 (10)−0.0041 (10)0.0039 (10)
C60.0421 (13)0.0340 (12)0.0568 (16)−0.0008 (11)−0.0051 (12)0.0095 (11)
C70.0545 (15)0.0359 (12)0.0643 (18)−0.0083 (13)−0.0085 (15)0.0165 (12)
C80.0496 (15)0.0446 (14)0.0585 (16)−0.0148 (13)−0.0025 (14)0.0183 (12)
C90.0384 (12)0.0419 (12)0.0435 (13)−0.0100 (11)−0.0018 (11)0.0085 (10)
C100.0343 (11)0.0453 (12)0.0343 (12)−0.0069 (11)0.0021 (10)0.0019 (10)
C110.0346 (12)0.0558 (15)0.0422 (14)0.0001 (12)0.0061 (11)−0.0010 (12)
C120.0351 (12)0.0383 (12)0.0614 (17)0.0041 (12)0.0017 (13)0.0055 (12)
C130.0356 (12)0.0358 (11)0.0484 (13)0.0036 (11)0.0057 (11)−0.0047 (10)
C140.0421 (14)0.0622 (17)0.0541 (16)0.0026 (14)0.0024 (13)0.0080 (14)
C150.0627 (19)0.070 (2)0.069 (2)0.0074 (18)0.0183 (18)0.0152 (17)
C160.0587 (19)0.0533 (17)0.079 (2)−0.0052 (16)0.0271 (18)0.0014 (16)
C170.0409 (15)0.0560 (16)0.075 (2)−0.0096 (14)0.0102 (15)−0.0176 (16)
C180.0393 (13)0.0485 (14)0.0537 (16)0.0006 (13)−0.0008 (12)−0.0098 (13)
C190.0379 (12)0.0392 (12)0.0424 (13)0.0074 (12)0.0065 (11)0.0095 (11)
C200.067 (2)0.0644 (19)0.0416 (16)0.0009 (18)0.0109 (15)0.0086 (14)
C210.0412 (13)0.0368 (11)0.0459 (14)0.0030 (11)0.0030 (11)−0.0015 (10)
C220.0560 (17)0.0377 (14)0.077 (2)−0.0051 (13)0.0028 (17)0.0161 (14)
C230.0543 (18)0.0556 (19)0.099 (3)−0.0072 (17)0.005 (2)0.023 (2)
Geometric parameters (Å, º) top
O1—C51.366 (3)C10—C111.381 (4)
O1—C121.434 (3)C11—H111.00 (3)
O2—C201.415 (3)C12—C131.495 (4)
O2—C191.425 (3)C12—H121.04 (3)
O3—C211.213 (3)C12—H12A0.97 (3)
O4—C211.327 (3)C13—C181.383 (4)
O4—C221.455 (3)C13—C141.381 (4)
N1—C111.328 (3)C14—C151.390 (4)
N1—C11.353 (3)C14—H141.03 (3)
N2—C101.374 (3)C15—C161.382 (5)
N2—C91.372 (3)C15—H151.05 (4)
N2—H20.91 (4)C16—C171.371 (5)
C1—C21.396 (3)C16—H161.03 (4)
C1—C211.499 (3)C17—C181.381 (4)
C2—C31.406 (3)C17—H170.99 (4)
C2—C191.512 (3)C18—H180.88 (3)
C3—C101.417 (3)C19—H191.06 (3)
C3—C41.458 (3)C19—H19A1.06 (3)
C4—C51.409 (3)C20—H20A1.04 (4)
C4—C91.417 (3)C20—H201.09 (5)
C5—C61.397 (3)C20—H20B1.05 (4)
C6—C71.400 (4)C22—C231.488 (5)
C6—H61.01 (3)C22—H220.99 (4)
C7—C81.360 (4)C22—H22A1.01 (4)
C7—H70.97 (3)C23—H230.92 (4)
C8—C91.403 (4)C23—H23A0.98 (5)
C8—H80.99 (3)C23—H23B0.97 (6)
C5—O1—C12117.22 (18)C18—C13—C14119.1 (3)
C20—O2—C19112.0 (2)C18—C13—C12120.7 (3)
C21—O4—C22117.5 (2)C14—C13—C12120.1 (2)
C11—N1—C1118.3 (2)C13—C14—C15120.7 (3)
C10—N2—C9108.9 (2)C13—C14—H14120.0 (19)
C10—N2—H2120 (2)C15—C14—H14119.3 (19)
C9—N2—H2130 (2)C16—C15—C14119.1 (3)
N1—C1—C2125.0 (2)C16—C15—H15123 (2)
N1—C1—C21111.9 (2)C14—C15—H15118 (2)
C2—C1—C21123.1 (2)C17—C16—C15120.7 (3)
C1—C2—C3116.6 (2)C17—C16—H16124 (2)
C1—C2—C19120.5 (2)C15—C16—H16116 (2)
C3—C2—C19122.2 (2)C16—C17—C18119.9 (3)
C2—C3—C10116.9 (2)C16—C17—H17121 (2)
C2—C3—C4137.0 (2)C18—C17—H17119 (2)
C10—C3—C4105.90 (19)C17—C18—C13120.5 (3)
C5—C4—C9117.7 (2)C17—C18—H18121 (2)
C5—C4—C3135.9 (2)C13—C18—H18119 (2)
C9—C4—C3105.9 (2)O2—C19—C2107.31 (19)
O1—C5—C6123.2 (2)O2—C19—H19108.4 (14)
O1—C5—C4117.52 (19)C2—C19—H19112.5 (14)
C6—C5—C4119.2 (2)O2—C19—H19A110.7 (15)
C5—C6—C7120.3 (3)C2—C19—H19A110.9 (15)
C5—C6—H6119.2 (18)H19—C19—H19A107 (2)
C7—C6—H6120.5 (17)O2—C20—H20A108 (2)
C8—C7—C6122.5 (2)O2—C20—H20108 (2)
C8—C7—H7119.2 (19)H20A—C20—H20113 (3)
C6—C7—H7118.3 (19)O2—C20—H20B108 (2)
C7—C8—C9117.1 (3)H20A—C20—H20B108 (3)
C7—C8—H8121.3 (18)H20—C20—H20B111 (3)
C9—C8—H8121.6 (18)O3—C21—O4123.6 (2)
N2—C9—C8127.4 (2)O3—C21—C1124.5 (2)
N2—C9—C4109.6 (2)O4—C21—C1111.8 (2)
C8—C9—C4122.9 (3)O4—C22—C23106.9 (3)
N2—C10—C11128.6 (2)O4—C22—H22108 (2)
N2—C10—C3109.6 (2)C23—C22—H22113 (2)
C11—C10—C3121.8 (2)O4—C22—H22A106 (2)
N1—C11—C10120.8 (2)C23—C22—H22A116 (2)
N1—C11—H11113.8 (17)H22—C22—H22A106 (3)
C10—C11—H11125.3 (17)C22—C23—H23112 (2)
O1—C12—C13108.5 (2)C22—C23—H23A109 (3)
O1—C12—H12109.5 (17)H23—C23—H23A106 (3)
C13—C12—H12111.4 (17)C22—C23—H23B110 (3)
O1—C12—H12A106.9 (18)H23—C23—H23B115 (4)
C13—C12—H12A111.2 (18)H23A—C23—H23B105 (4)
H12—C12—H12A109 (2)
(FG7142) '3-carbomethylamide-beta-carboline' top
Crystal data top
C13H11N3OF(000) = 944
Mr = 225.25Dx = 1.379 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71070 Å
a = 14.3632 (5) ÅCell parameters from 5605 reflections
b = 7.6804 (2) Åθ = 2.8–28.0°
c = 19.6712 (7) ŵ = 0.09 mm−1
β = 90.9340 (12)°T = 293 K
V = 2169.74 (12) Å3Prism, colourless
Z = 80.4 × 0.31 × 0.17 mm
Data collection top
Nonius KappaCCD
diffractometer		1943 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 28.0°, θmin = 2.8°
ϕ scans and ω scansh = −18→18
5605 measured reflectionsk = −10→10
2595 independent reflectionsl = −25→25
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)] = 0.048Hydrogen site location: difference Fourier map
wR(F2) = 0.148H atoms treated by a mixture of independent and constrained refinement
S = 1.13 w = 1/[σ2(Fo2) + (0.0753P)2 + 0.5664P]
where P = (Fo2 + 2Fc2)/3
2595 reflections(Δ/σ)max = 0.054
190 parametersΔρmax = 0.18 e Å−3
0 restraintsΔρmin = −0.19 e Å−3
Crystal data top
C13H11N3OV = 2169.74 (12) Å3
Mr = 225.25Z = 8
Monoclinic, C2/cMo Kα radiation
a = 14.3632 (5) ŵ = 0.09 mm−1
b = 7.6804 (2) ÅT = 293 K
c = 19.6712 (7) Å0.4 × 0.31 × 0.17 mm
β = 90.9340 (12)°
Data collection top
Nonius KappaCCD
diffractometer		1943 reflections with I > 2σ(I)
5605 measured reflectionsRint = 0.026
2595 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.148H atoms treated by a mixture of independent and constrained refinement
S = 1.13Δρmax = 0.18 e Å−3
2595 reflectionsΔρmin = −0.19 e Å−3
190 parameters
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*/Ueq
O10.58381 (8)−0.36399 (17)0.46815 (6)0.0570 (4)
N10.36748 (9)−0.16612 (19)0.42480 (7)0.0498 (4)
N20.23372 (10)0.06983 (19)0.55375 (7)0.0518 (4)
N30.49408 (11)−0.3831 (2)0.37370 (8)0.0558 (4)
C10.43745 (10)−0.2174 (2)0.46727 (8)0.0428 (4)
C20.44311 (10)−0.1742 (2)0.53534 (8)0.0423 (4)
C30.37158 (10)−0.0755 (2)0.56223 (8)0.0415 (4)
C40.34920 (11)−0.0076 (2)0.62828 (8)0.0438 (4)
C50.39386 (13)−0.0108 (2)0.69155 (8)0.0496 (4)
C60.35221 (14)0.0692 (3)0.74602 (10)0.0577 (5)
C70.26660 (14)0.1533 (3)0.73774 (10)0.0611 (5)
C80.22109 (14)0.1601 (3)0.67569 (10)0.0592 (5)
C90.26317 (11)0.0796 (2)0.62058 (9)0.0490 (4)
C100.29810 (11)−0.0242 (2)0.51805 (8)0.0451 (4)
C110.29930 (12)−0.0701 (2)0.44976 (9)0.0519 (4)
C120.51162 (11)−0.3272 (2)0.43680 (8)0.0444 (4)
C130.56143 (16)−0.4803 (3)0.33525 (10)0.0688 (6)
H1310.5295−0.55910.30500.155 (13)*
H1320.6009−0.54510.36590.129 (11)*
H1330.5986−0.40130.30930.141 (13)*
H1N0.1739 (16)0.113 (3)0.5357 (11)0.075 (6)*
H110.2477 (14)−0.030 (3)0.4186 (10)0.062 (5)*
H3N0.4406 (16)−0.340 (3)0.3545 (11)0.067 (6)*
H20.4976 (12)−0.214 (2)0.5624 (8)0.043 (4)*
H50.4538 (14)−0.070 (3)0.6965 (9)0.056 (5)*
H60.3828 (13)0.068 (3)0.7909 (11)0.060 (5)*
H70.2373 (15)0.215 (3)0.7774 (11)0.074 (6)*
H80.1618 (13)0.219 (2)0.6688 (9)0.056 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0472 (6)0.0704 (8)0.0531 (7)0.0083 (6)−0.0097 (5)0.0013 (6)
N10.0491 (7)0.0590 (8)0.0409 (7)0.0037 (6)−0.0098 (6)0.0041 (6)
N20.0437 (7)0.0605 (9)0.0510 (8)0.0072 (6)−0.0066 (6)0.0030 (7)
N30.0553 (8)0.0685 (10)0.0434 (8)0.0089 (7)−0.0058 (7)−0.0019 (7)
C10.0421 (8)0.0455 (8)0.0405 (8)−0.0031 (6)−0.0062 (6)0.0063 (6)
C20.0393 (7)0.0472 (8)0.0403 (8)−0.0015 (6)−0.0070 (6)0.0075 (6)
C30.0408 (8)0.0431 (8)0.0403 (8)−0.0052 (6)−0.0055 (6)0.0060 (6)
C40.0446 (8)0.0453 (8)0.0415 (8)−0.0040 (6)−0.0018 (6)0.0043 (6)
C50.0534 (9)0.0513 (9)0.0440 (9)−0.0013 (7)−0.0052 (7)0.0005 (7)
C60.0706 (12)0.0577 (10)0.0448 (10)−0.0046 (8)−0.0026 (8)−0.0004 (8)
C70.0698 (12)0.0610 (11)0.0527 (11)−0.0011 (9)0.0113 (9)−0.0042 (9)
C80.0545 (10)0.0623 (11)0.0612 (11)0.0051 (8)0.0071 (8)0.0001 (9)
C90.0460 (8)0.0512 (9)0.0496 (9)−0.0031 (7)−0.0013 (7)0.0041 (7)
C100.0431 (8)0.0470 (9)0.0450 (9)−0.0010 (6)−0.0058 (6)0.0058 (7)
C110.0475 (9)0.0622 (10)0.0457 (9)0.0058 (8)−0.0129 (7)0.0075 (8)
C120.0450 (8)0.0465 (9)0.0416 (8)−0.0039 (6)−0.0034 (6)0.0072 (7)
C130.0772 (13)0.0785 (14)0.0509 (11)0.0150 (11)0.0041 (10)−0.0035 (10)
Geometric parameters (Å, º) top
O1—C121.2305 (18)C4—C51.391 (2)
N1—C111.326 (2)C4—C91.412 (2)
N1—C11.3548 (19)C5—C61.380 (3)
N2—C101.375 (2)C5—H50.97 (2)
N2—C91.376 (2)C6—C71.396 (3)
N2—H1N0.98 (2)C6—H60.98 (2)
N3—C121.333 (2)C7—C81.376 (3)
N3—C131.446 (2)C7—H71.01 (2)
N3—H3N0.91 (2)C8—C91.394 (3)
C1—C21.381 (2)C8—H80.971 (19)
C1—C121.492 (2)C10—C111.389 (2)
C2—C31.388 (2)C11—H111.00 (2)
C2—H20.988 (16)C13—H1310.9600
C3—C101.412 (2)C13—H1320.9600
C3—C41.441 (2)C13—H1330.9600
C11—N1—C1118.56 (14)C8—C7—C6121.71 (18)
C10—N2—C9108.51 (13)C8—C7—H7118.0 (12)
C10—N2—H1N125.8 (13)C6—C7—H7120.2 (12)
C9—N2—H1N125.5 (13)C7—C8—C9117.86 (18)
C12—N3—C13122.38 (16)C7—C8—H8123.0 (11)
C12—N3—H3N114.6 (13)C9—C8—H8119.1 (11)
C13—N3—H3N122.4 (13)N2—C9—C8129.53 (16)
N1—C1—C2124.01 (15)N2—C9—C4109.36 (15)
N1—C1—C12116.36 (13)C8—C9—C4121.11 (16)
C2—C1—C12119.63 (13)N2—C10—C11130.25 (14)
C1—C2—C3117.95 (13)N2—C10—C3109.53 (14)
C1—C2—H2118.8 (10)C11—C10—C3120.23 (15)
C3—C2—H2123.2 (10)N1—C11—C10121.32 (14)
C2—C3—C10117.91 (14)N1—C11—H11119.1 (11)
C2—C3—C4135.91 (14)C10—C11—H11119.5 (11)
C10—C3—C4106.17 (14)O1—C12—N3122.51 (16)
C5—C4—C9119.64 (16)O1—C12—C1121.99 (14)
C5—C4—C3133.94 (16)N3—C12—C1115.49 (14)
C9—C4—C3106.41 (14)N3—C13—H131109.5
C6—C5—C4119.17 (17)N3—C13—H132109.5
C6—C5—H5121.5 (11)H131—C13—H132109.5
C4—C5—H5119.4 (11)N3—C13—H133109.5
C5—C6—C7120.50 (18)H131—C13—H133109.5
C5—C6—H6120.0 (12)H132—C13—H133109.5
C7—C6—H6119.5 (12)
(Harmine) '1-methyl-7-methoxy-beta-carboline hydrochloride hemihydrate' top
Crystal data top
[C13H13N2O]+Cl−.1/2H2OF(000) = 1080
Mr = 257.71Dx = 1.372 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71070 Å
a = 16.9891 (4) ÅCell parameters from 6879 reflections
b = 12.5409 (3) Åθ = 2.2–29.0°
c = 13.7967 (4) ŵ = 0.30 mm−1
β = 121.8960 (11)°T = 150 K
V = 2495.66 (11) Å3Prism, colourless
Z = 80.28 × 0.17 × 0.14 mm
Data collection top
Nonius Kappa CCD
diffractometer		2448 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 29.0°, θmin = 2.2°
ϕ scans and ω scansh = −23→23
6879 measured reflectionsk = −17→17
3317 independent reflectionsl = −18→18
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)] = 0.047Hydrogen site location: difference Fourier map
wR(F2) = 0.129All H-atom parameters refined
S = 1.14 w = 1/[σ2(Fo2) + (0.0504P)2 + 2.3654P]
where P = (Fo2 + 2Fc2)/3
3317 reflections(Δ/σ)max = 0.002
223 parametersΔρmax = 0.28 e Å−3
0 restraintsΔρmin = −0.37 e Å−3
Crystal data top
[C13H13N2O]+Cl−.1/2H2OV = 2495.66 (11) Å3
Mr = 257.71Z = 8
Monoclinic, C2/cMo Kα radiation
a = 16.9891 (4) ŵ = 0.30 mm−1
b = 12.5409 (3) ÅT = 150 K
c = 13.7967 (4) Å0.28 × 0.17 × 0.14 mm
β = 121.8960 (11)°
Data collection top
Nonius Kappa CCD
diffractometer		2448 reflections with I > 2σ(I)
6879 measured reflectionsRint = 0.023
3317 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.129All H-atom parameters refined
S = 1.14Δρmax = 0.28 e Å−3
3317 reflectionsΔρmin = −0.37 e Å−3
223 parameters
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)
Cl10.38994 (4)−0.32444 (4)0.49179 (5)0.0465 (2)
N10.70678 (11)−0.07274 (13)0.81154 (13)0.0259 (3)
N20.46159 (10)−0.09512 (13)0.59262 (12)0.0228 (3)
O10.18797 (9)0.12404 (11)0.34200 (12)0.0345 (3)
O20.5625 (2)−0.4350 (3)0.5011 (3)0.0439 (8)0.50
C10.71514 (13)0.03540 (16)0.81693 (16)0.0276 (4)
C20.64032 (13)0.09922 (15)0.74890 (15)0.0256 (4)
C30.55588 (12)0.04919 (14)0.67395 (14)0.0224 (4)
C40.46465 (12)0.08646 (14)0.59233 (14)0.0222 (4)
C50.42501 (13)0.18820 (15)0.55673 (16)0.0260 (4)
C60.33281 (14)0.19498 (15)0.47417 (16)0.0282 (4)
C70.27774 (13)0.10251 (15)0.42477 (15)0.0263 (4)
C80.31402 (13)0.00113 (15)0.45854 (15)0.0240 (4)
C90.40882 (12)−0.00486 (13)0.54333 (14)0.0218 (4)
C100.55110 (12)−0.06383 (14)0.67111 (14)0.0215 (4)
C110.62780 (12)−0.12611 (14)0.74170 (14)0.0233 (4)
C120.12682 (15)0.03556 (19)0.2891 (2)0.0379 (5)
C130.62893 (15)−0.24479 (16)0.74852 (18)0.0303 (4)
H1N0.7611 (17)−0.1114 (19)0.862 (2)0.043 (6)*
H20.6489 (15)0.1767 (18)0.7546 (18)0.034 (6)*
H10.7782 (15)0.0607 (16)0.8719 (18)0.031 (5)*
H60.3047 (14)0.2613 (18)0.4507 (17)0.030 (5)*
H1210.1514 (18)−0.013 (2)0.252 (2)0.050 (7)*
H1310.6870 (19)−0.270 (2)0.768 (2)0.053 (7)*
H1220.0679 (16)0.0655 (18)0.2316 (19)0.036 (6)*
H50.4615 (14)0.2537 (18)0.5878 (17)0.028 (5)*
H1230.1216 (16)−0.0071 (19)0.348 (2)0.042 (6)*
H80.2753 (15)−0.0634 (17)0.4272 (19)0.034 (6)*
H2N0.4456 (16)−0.158 (2)0.5710 (19)0.034 (6)*
H1320.583 (2)−0.275 (2)0.678 (3)0.060 (8)*
H1330.6195 (18)−0.269 (2)0.809 (2)0.059 (8)*
H1O0.562 (4)−0.503 (6)0.502 (5)0.066 (18)*0.50
H2O0.508 (6)−0.414 (6)0.501 (6)0.09 (2)*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0302 (3)0.0376 (3)0.0521 (4)−0.0047 (2)0.0084 (2)−0.0188 (2)
N10.0228 (8)0.0293 (8)0.0210 (7)0.0028 (6)0.0086 (6)0.0004 (6)
N20.0233 (8)0.0203 (8)0.0224 (7)−0.0002 (6)0.0104 (6)−0.0008 (6)
O10.0260 (7)0.0364 (8)0.0309 (7)0.0085 (6)0.0080 (6)0.0029 (6)
O20.0334 (17)0.0308 (17)0.057 (2)−0.0014 (13)0.0165 (15)0.0009 (14)
C10.0253 (10)0.0314 (10)0.0240 (9)−0.0026 (8)0.0115 (8)−0.0048 (7)
C20.0278 (10)0.0260 (9)0.0245 (9)−0.0023 (7)0.0148 (8)−0.0030 (7)
C30.0260 (9)0.0241 (9)0.0201 (8)0.0007 (7)0.0142 (7)−0.0004 (6)
C40.0248 (9)0.0240 (9)0.0194 (8)0.0012 (7)0.0127 (7)0.0008 (6)
C50.0297 (10)0.0229 (9)0.0270 (9)0.0021 (7)0.0161 (8)0.0020 (7)
C60.0320 (10)0.0242 (9)0.0286 (9)0.0078 (7)0.0162 (9)0.0051 (7)
C70.0242 (9)0.0337 (10)0.0218 (8)0.0065 (7)0.0129 (8)0.0028 (7)
C80.0233 (9)0.0281 (9)0.0210 (8)0.0011 (7)0.0119 (8)−0.0003 (7)
C90.0246 (9)0.0244 (9)0.0197 (8)0.0021 (7)0.0138 (7)0.0016 (6)
C100.0230 (9)0.0239 (8)0.0187 (8)0.0001 (7)0.0118 (7)−0.0005 (6)
C110.0247 (9)0.0267 (9)0.0198 (8)0.0013 (7)0.0126 (8)0.0002 (7)
C120.0254 (10)0.0449 (12)0.0346 (11)0.0030 (9)0.0099 (9)0.0032 (10)
C130.0310 (11)0.0263 (10)0.0302 (10)0.0037 (8)0.0138 (9)0.0027 (8)
Geometric parameters (Å, º) top
N1—C111.346 (2)C4—C91.411 (2)
N1—C11.362 (2)C5—C61.369 (3)
N1—H1N0.94 (2)C5—H50.98 (2)
N2—C101.378 (2)C6—C71.418 (3)
N2—C91.380 (2)C6—H60.93 (2)
N2—H2N0.84 (2)C7—C81.382 (3)
O1—C71.365 (2)C8—C91.406 (3)
O1—C121.429 (3)C8—H80.99 (2)
O2—H1O0.86 (7)C10—C111.384 (2)
O2—H2O0.96 (8)C11—C131.491 (3)
C1—C21.370 (3)C12—H1211.02 (3)
C1—H10.98 (2)C12—H1220.97 (2)
C2—C31.398 (3)C12—H1231.01 (2)
C2—H20.98 (2)C13—H1310.93 (3)
C3—C101.419 (2)C13—H1320.94 (3)
C3—C41.430 (2)C13—H1330.97 (3)
C4—C51.405 (2)
C11—N1—C1124.77 (16)O1—C7—C6113.71 (16)
C11—N1—H1N119.2 (15)C8—C7—C6121.80 (17)
C1—N1—H1N116.0 (15)C7—C8—C9116.12 (17)
C10—N2—C9108.28 (15)C7—C8—H8122.1 (13)
C10—N2—H2N124.3 (16)C9—C8—H8121.8 (13)
C9—N2—H2N126.5 (16)N2—C9—C8127.90 (16)
C7—O1—C12117.59 (16)N2—C9—C4109.42 (15)
H1O—O2—H2O104 (5)C8—C9—C4122.68 (16)
N1—C1—C2120.82 (17)N2—C10—C11129.06 (16)
N1—C1—H1113.8 (12)N2—C10—C3109.23 (15)
C2—C1—H1125.4 (12)C11—C10—C3121.69 (16)
C1—C2—C3117.57 (17)N1—C11—C10115.80 (16)
C1—C2—H2118.7 (13)N1—C11—C13118.46 (16)
C3—C2—H2123.8 (13)C10—C11—C13125.72 (17)
C2—C3—C10119.35 (16)O1—C12—H121110.1 (14)
C2—C3—C4134.25 (17)O1—C12—H122106.0 (13)
C10—C3—C4106.40 (15)H121—C12—H122110.2 (19)
C5—C4—C9119.54 (16)O1—C12—H123110.4 (13)
C5—C4—C3133.81 (17)H121—C12—H123108.3 (19)
C9—C4—C3106.66 (15)H122—C12—H123111.8 (18)
C6—C5—C4118.29 (17)C11—C13—H131109.8 (16)
C6—C5—H5119.5 (12)C11—C13—H132110.9 (17)
C4—C5—H5122.2 (12)H131—C13—H132109 (2)
C5—C6—C7121.57 (17)C11—C13—H133111.0 (16)
C5—C6—H6119.8 (13)H131—C13—H133106 (2)
C7—C6—H6118.6 (13)H132—C13—H133110 (2)
O1—C7—C8124.49 (17)

Experimental details

(ZK93423)(ZK91296)(FG7142)(Harmine)
Crystal data
Chemical formulaC23H22N2O4C23H22N2O4C13H11N3O[C13H13N2O]+Cl−.1/2H2O
Mr390.43390.43225.25257.71
Crystal system, space groupMonoclinic, P21Orthorhombic, P212121Monoclinic, C2/cMonoclinic, C2/c
Temperature (K)100293293150
a, b, c (Å)5.0472 (2), 11.3381 (5), 16.8796 (7)9.9033 (5), 11.5758 (4), 17.1805 (9)14.3632 (5), 7.6804 (2), 19.6712 (7)16.9891 (4), 12.5409 (3), 13.7967 (4)
α, β, γ (°)90, 94.331 (3), 9090, 90, 9090, 90.9340 (12), 9090, 121.8960 (11), 90
V (Å3)963.19 (7)1969.58 (16)2169.74 (12)2495.66 (11)
Z2488
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm−1)0.090.090.090.30
Crystal size (mm)0.5 × 0.24 × 0.070.45 × 0.30 × 0.090.4 × 0.31 × 0.170.28 × 0.17 × 0.14
Data collection
DiffractometerNonius Kappa CCD
diffractometer		Nonius Kappa CCD
diffractometer		Nonius KappaCCD
diffractometer		Nonius Kappa CCD
diffractometer
Absorption correction––––
No. of measured, independent and
observed [I > 2σ(I)] reflections		4907, 2664, 2316 5595, 3201, 2330 5605, 2595, 1943 6879, 3317, 2448
Rint0.0340.0330.0260.023
(sin θ/λ)max (Å−1)0.6820.7040.6600.682
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.103, 1.08 0.048, 0.111, 1.04 0.048, 0.148, 1.13 0.047, 0.129, 1.14
No. of reflections2664320125953317
No. of parameters349350190223
H-atom treatmentAll H-atom parameters refinedAll H-atom parameters refinedH atoms treated by a mixture of independent and constrained refinementAll H-atom parameters refined
Δρmax, Δρmin (e Å−3)0.38, −0.280.18, −0.180.18, −0.190.28, −0.37
Absolute structureFlack H D (1983), Acta Cryst. A39, 876-881Flack H D (1983), Acta Cryst. A39, 876-881??
Absolute structure parameter1.4 (13)−1.7 (15)??

Computer programs: Kappa CCD server software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), ORTEP (Burnett & Johnson, 1996), ORTEP(Burnett & Johnson, 1996), SHELXL97 (Sheldrick, 1997); PARST (Nardelli, 1983, 1995); PLATON (Spek, 1998).

 

Subscribe to Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. B
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS