organic compounds
[2-(3,4-Dimethoxyphenyl)ethyl](3-{N-[2-(3,4-dimethoxyphenyl)ethyl]carbamoyl}propyl)azanium chloride dihydrate
aS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent 100170, Uzbekistan
*Correspondence e-mail: a-saidov85@mail.ru
The 24H35N2O5+·Cl−·2H2O, contains one organic cation that has its protonation site at the amine function, one chloride anion and two lattice water molecules. In the crystal, one pair of lattice water molecules and two chloride anions form a four-membered centrosymmetric hydrogen-bond cycle. In addition, O—H⋯O, N—H⋯O and N—H⋯Cl hydrogen bonds involving the N—H groups, the water molecules and the C=O group are observed. As a result, a hydrogen-bonded layer parallel to (100) is formed. The thickness of such a layer corresponds to the length of the a axis [21.977 (3) Å].
of the title hydrated salt, CCCDC reference: 983858
Related literature
For standard bond lengths, see: Allen et al. (1987). For the synthesis of related compounds, see: Bentley (2006); Saidov et al. (2013). For the of a related compound, see: Peters et al. (1994).
Experimental
Crystal data
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Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
CCDC reference: 983858
10.1107/S1600536814001998/wm2799sup1.cif
contains datablocks I, GLOBAL. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001998/wm2799Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814001998/wm2799Isup3.cml
To a solution of 2.0 g. (0.004 mol) N,N-(3,4-dimethoxyphenyl ethyl)succindiamide in 30 ml absolute benzene was added 6.7 g (0.04 mol) POCl3. The reaction mixture was boiled for 2 h. Benzene and excess POCl3 were then removed under reduced pressure, and the residue was dissolved in 30 ml methanol. To the received solution was added 3.8 g (0.1 mol) NaBH4 at 273-278 K under ice cooling. Then methanol was removed, the residue dissolved in water and extracted with chloroform. From the chloroformic layer were obtained three componds with Rf 0.9, 0.5 and 0.2 (title compound) (chloroform:methanol=8:1). The compounds were isolated by ν, cm-1): 3434, 3258, 2940, 1651, 1590, 1519. Crystals suitable for X-ray were obtained from a chloroform–methanol (8:1) mixture by slow evaporation.
(silica gel); 0.075 g of the title compound were obtained with a m.p. 406-408 K. IR (KBr,Carbon-bound H atoms were placed geometrically and treated as riding on their parent atoms, with C—H distances of 0.93 Å (aromatic), 0.97 Å (methylen), 0.96 Å (methyl) and were refined with Uiso(H)=1.2Ueq(C) for aromatic and methylen H atoms, Uiso(H)=1.5Ueq(C) for methyl H atoms. N-bound H atoms and water H atoms involved in the intermolecular hydrogen bonding were found by difference Fourier synthesis and refined isotropically [N1–H1=0.86 (2) Å, N2–H2 0.92 (3) Å, N2–H3 0.99 (3) Å, O1W–H1W1= 0.86 (5) Å, O1W–H2W1= 0.91 (5) Å, O2W–H1W2= 0.96 (4) Å, O2W–H2W2= 0.80 (4) Å].
The title compound, C24H35N2O5+.Cl-(H2O)2, was isolated as an intermediate product in the synthesis of isoquinoline alkaloid analogues (Saidov et al., 2013). Similar compounds have been synthesized (Bentley, 2006), or their structures characterized (Peters et al., 1994).
A perspective view of the moleculular entities of the title compound, showing the atomic numbering scheme, is given in Fig. 1. Bond lengths and angles are in normal ranges (Allen et al., 1987). The organic molecule contains two N atoms, amidic and aminic. The N atom on an amide is usually less nucleophilic than the N atom of an amine, due to the resonance stabilization of the N atom lone-pair provided by the amide carbonyl group. Therefore, in the cation the protonization of the amino N atom is observed.
In the ═O···H—O(w) hydrogen bonds (Table 1). As a result, hydrogen-bonded layers parallel to (100) are formed that have a thickness corresponding to the length of the a axis.
two chloride anion and one lattice water molecule form a centrosymmetric four-membered hydrogen-bonding cycle (Fig. 2). The protonated organic molecules are bridged by N—H···Cl and CFor standard bond lengths, see: Allen et al. (1987). For the synthesis of related compounds, see: Bentley (2006); Saidov et al. (2013). For the
of a related compound, see: Peters et al. (1994).Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell
CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. The molecular entities of the title compound with displacement ellipsoids drawn at the 50% probability level. | |
Fig. 2. The crystal packing of the title compound showing hydrogen bonds (dashed lines) |
C24H35N2O5+·Cl−·2H2O | F(000) = 1080 |
Mr = 503.02 | Dx = 1.218 Mg m−3 |
Monoclinic, P21/c | Melting point: 406(2) K |
Hall symbol: -P 2ybc | Cu Kα radiation, λ = 1.54184 Å |
a = 21.977 (3) Å | Cell parameters from 3039 reflections |
b = 12.2295 (10) Å | θ = 3.6–67.2° |
c = 10.2217 (9) Å | µ = 1.59 mm−1 |
β = 93.490 (9)° | T = 295 K |
V = 2742.2 (5) Å3 | Prism, colourless |
Z = 4 | 0.60 × 0.40 × 0.35 mm |
Oxford Diffraction Xcalibur Ruby diffractometer | 4860 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 3012 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
Detector resolution: 10.2576 pixels mm-1 | θmax = 67.3°, θmin = 4.0° |
ω scans | h = −25→26 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | k = −14→12 |
Tmin = 0.599, Tmax = 1.000 | l = −12→12 |
11225 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.131 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0748P)2] where P = (Fo2 + 2Fc2)/3 |
4860 reflections | (Δ/σ)max = 0.001 |
339 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C24H35N2O5+·Cl−·2H2O | V = 2742.2 (5) Å3 |
Mr = 503.02 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 21.977 (3) Å | µ = 1.59 mm−1 |
b = 12.2295 (10) Å | T = 295 K |
c = 10.2217 (9) Å | 0.60 × 0.40 × 0.35 mm |
β = 93.490 (9)° |
Oxford Diffraction Xcalibur Ruby diffractometer | 4860 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | 3012 reflections with I > 2σ(I) |
Tmin = 0.599, Tmax = 1.000 | Rint = 0.035 |
11225 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.131 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | Δρmax = 0.20 e Å−3 |
4860 reflections | Δρmin = −0.24 e Å−3 |
339 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.60316 (3) | 0.54002 (5) | 0.43730 (7) | 0.0681 (2) | |
O1 | 0.04553 (8) | 0.60760 (16) | −0.00797 (18) | 0.0712 (5) | |
O2 | 0.04433 (7) | 0.62103 (15) | 0.24413 (18) | 0.0680 (5) | |
O3 | 0.35306 (8) | 0.87255 (13) | 0.4546 (2) | 0.0689 (5) | |
O4 | 0.83315 (9) | 1.01542 (13) | 0.90785 (19) | 0.0709 (5) | |
O5 | 0.89012 (7) | 0.84794 (15) | 1.01019 (17) | 0.0636 (5) | |
N1 | 0.33989 (9) | 0.69124 (17) | 0.4423 (2) | 0.0553 (5) | |
N2 | 0.59396 (8) | 0.76971 (17) | 0.5691 (2) | 0.0460 (5) | |
C1 | 0.21020 (10) | 0.58872 (18) | 0.2146 (2) | 0.0503 (6) | |
C2 | 0.21035 (11) | 0.5805 (2) | 0.0803 (2) | 0.0584 (6) | |
H2A | 0.2469 | 0.5712 | 0.0405 | 0.070* | |
C3 | 0.15577 (12) | 0.5863 (2) | 0.0040 (2) | 0.0605 (6) | |
H3A | 0.1565 | 0.5803 | −0.0866 | 0.073* | |
C4 | 0.10113 (11) | 0.60055 (19) | 0.0590 (2) | 0.0520 (6) | |
C5 | 0.10050 (10) | 0.60831 (18) | 0.1960 (2) | 0.0498 (6) | |
C6 | 0.15446 (10) | 0.60152 (19) | 0.2707 (2) | 0.0504 (6) | |
H6A | 0.1538 | 0.6056 | 0.3614 | 0.061* | |
C7 | 0.04354 (15) | 0.5862 (3) | −0.1458 (3) | 0.0874 (10) | |
H7A | 0.0020 | 0.5880 | −0.1807 | 0.131* | |
H7B | 0.0606 | 0.5153 | −0.1608 | 0.131* | |
H7C | 0.0667 | 0.6408 | −0.1883 | 0.131* | |
C8 | 0.03998 (14) | 0.6059 (3) | 0.3813 (3) | 0.0794 (9) | |
H8A | −0.0021 | 0.6062 | 0.4014 | 0.119* | |
H8B | 0.0611 | 0.6641 | 0.4279 | 0.119* | |
H8C | 0.0581 | 0.5372 | 0.4072 | 0.119* | |
C9 | 0.26858 (11) | 0.58427 (19) | 0.3007 (3) | 0.0574 (6) | |
H9A | 0.3003 | 0.5506 | 0.2525 | 0.069* | |
H9B | 0.2623 | 0.5393 | 0.3768 | 0.069* | |
C10 | 0.28909 (10) | 0.69740 (19) | 0.3453 (3) | 0.0557 (6) | |
H10A | 0.3011 | 0.7391 | 0.2704 | 0.067* | |
H10B | 0.2554 | 0.7352 | 0.3824 | 0.067* | |
C11 | 0.36817 (10) | 0.77996 (19) | 0.4917 (2) | 0.0503 (6) | |
C12 | 0.42055 (10) | 0.76099 (19) | 0.5905 (3) | 0.0514 (6) | |
H12A | 0.4174 | 0.6882 | 0.6273 | 0.062* | |
H12B | 0.4185 | 0.8134 | 0.6613 | 0.062* | |
C13 | 0.48157 (10) | 0.7724 (2) | 0.5283 (2) | 0.0544 (6) | |
H13A | 0.4860 | 0.7135 | 0.4661 | 0.065* | |
H13B | 0.4824 | 0.8410 | 0.4808 | 0.065* | |
C14 | 0.53415 (10) | 0.7694 (2) | 0.6305 (2) | 0.0519 (6) | |
H14A | 0.5319 | 0.8324 | 0.6876 | 0.062* | |
H14B | 0.5311 | 0.7041 | 0.6836 | 0.062* | |
C15 | 0.64681 (10) | 0.7750 (2) | 0.6672 (2) | 0.0548 (6) | |
H15A | 0.6467 | 0.7105 | 0.7225 | 0.066* | |
H15B | 0.6425 | 0.8385 | 0.7226 | 0.066* | |
C16 | 0.70733 (10) | 0.7816 (2) | 0.6030 (3) | 0.0602 (7) | |
H16A | 0.7139 | 0.7152 | 0.5539 | 0.072* | |
H16B | 0.7068 | 0.8428 | 0.5426 | 0.072* | |
C17 | 0.75800 (10) | 0.7962 (2) | 0.7074 (2) | 0.0518 (6) | |
C18 | 0.77208 (10) | 0.9006 (2) | 0.7562 (2) | 0.0516 (6) | |
H18A | 0.7513 | 0.9609 | 0.7205 | 0.062* | |
C19 | 0.81614 (10) | 0.91564 (18) | 0.8559 (2) | 0.0502 (6) | |
C20 | 0.84737 (10) | 0.82529 (19) | 0.9117 (2) | 0.0491 (6) | |
C21 | 0.83303 (11) | 0.72290 (19) | 0.8639 (3) | 0.0604 (7) | |
H21A | 0.8532 | 0.6621 | 0.8999 | 0.072* | |
C22 | 0.78904 (11) | 0.7091 (2) | 0.7631 (3) | 0.0621 (7) | |
H22A | 0.7803 | 0.6390 | 0.7321 | 0.074* | |
C23 | 0.79880 (15) | 1.1081 (2) | 0.8642 (3) | 0.0781 (9) | |
H23A | 0.8149 | 1.1723 | 0.9079 | 0.117* | |
H23B | 0.7570 | 1.0984 | 0.8838 | 0.117* | |
H23C | 0.8013 | 1.1163 | 0.7713 | 0.117* | |
C24 | 0.91979 (13) | 0.7568 (2) | 1.0737 (3) | 0.0776 (9) | |
H24A | 0.9487 | 0.7826 | 1.1408 | 0.116* | |
H24B | 0.9406 | 0.7150 | 1.0106 | 0.116* | |
H24C | 0.8900 | 0.7116 | 1.1123 | 0.116* | |
O1W | 0.46801 (16) | 0.5117 (2) | 0.3085 (3) | 0.0915 (7) | |
O2W | 0.40073 (12) | 1.04928 (17) | 0.5826 (3) | 0.0892 (8) | |
H1W2 | 0.3843 (19) | 0.987 (4) | 0.537 (4) | 0.159 (17)* | |
H2W2 | 0.4236 (18) | 1.034 (3) | 0.644 (4) | 0.116 (15)* | |
H1W1 | 0.448 (2) | 0.495 (4) | 0.376 (5) | 0.16 (2)* | |
H2W1 | 0.509 (2) | 0.513 (4) | 0.330 (4) | 0.16 (2)* | |
H1 | 0.3518 (11) | 0.629 (2) | 0.476 (2) | 0.058 (7)* | |
H2 | 0.5971 (11) | 0.707 (2) | 0.520 (3) | 0.071 (8)* | |
H3 | 0.5953 (10) | 0.834 (2) | 0.511 (2) | 0.062 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0868 (5) | 0.0462 (3) | 0.0703 (4) | 0.0017 (3) | −0.0030 (3) | 0.0004 (3) |
O1 | 0.0576 (11) | 0.0906 (14) | 0.0628 (11) | −0.0020 (10) | −0.0185 (9) | 0.0016 (10) |
O2 | 0.0452 (10) | 0.0919 (14) | 0.0668 (12) | 0.0045 (9) | 0.0015 (8) | −0.0032 (10) |
O3 | 0.0586 (11) | 0.0429 (10) | 0.1020 (15) | 0.0001 (8) | −0.0209 (10) | 0.0039 (9) |
O4 | 0.0856 (13) | 0.0493 (10) | 0.0745 (12) | 0.0019 (9) | −0.0230 (10) | −0.0066 (9) |
O5 | 0.0515 (10) | 0.0699 (11) | 0.0673 (11) | −0.0008 (8) | −0.0153 (8) | 0.0052 (9) |
N1 | 0.0438 (11) | 0.0415 (11) | 0.0781 (15) | −0.0004 (9) | −0.0155 (10) | 0.0037 (11) |
N2 | 0.0391 (11) | 0.0452 (11) | 0.0529 (12) | −0.0006 (8) | −0.0044 (9) | −0.0062 (10) |
C1 | 0.0465 (13) | 0.0435 (12) | 0.0599 (15) | 0.0000 (10) | −0.0047 (11) | −0.0039 (11) |
C2 | 0.0507 (14) | 0.0662 (16) | 0.0585 (16) | −0.0026 (12) | 0.0052 (12) | −0.0041 (13) |
C3 | 0.0652 (17) | 0.0707 (16) | 0.0451 (14) | −0.0081 (14) | −0.0002 (12) | −0.0010 (12) |
C4 | 0.0505 (14) | 0.0507 (14) | 0.0535 (15) | −0.0061 (11) | −0.0074 (11) | 0.0030 (11) |
C5 | 0.0455 (13) | 0.0496 (13) | 0.0537 (14) | 0.0012 (10) | −0.0018 (11) | −0.0045 (11) |
C6 | 0.0498 (13) | 0.0551 (14) | 0.0456 (13) | −0.0004 (11) | −0.0031 (11) | −0.0037 (11) |
C7 | 0.092 (2) | 0.104 (2) | 0.0616 (19) | −0.0084 (19) | −0.0325 (17) | −0.0010 (17) |
C8 | 0.0722 (19) | 0.095 (2) | 0.072 (2) | 0.0049 (16) | 0.0203 (15) | 0.0011 (17) |
C9 | 0.0493 (14) | 0.0501 (13) | 0.0713 (17) | 0.0025 (11) | −0.0085 (12) | −0.0103 (13) |
C10 | 0.0440 (13) | 0.0493 (14) | 0.0720 (17) | −0.0024 (11) | −0.0109 (12) | 0.0022 (12) |
C11 | 0.0389 (12) | 0.0466 (14) | 0.0648 (16) | −0.0013 (10) | −0.0008 (11) | 0.0000 (11) |
C12 | 0.0421 (13) | 0.0456 (13) | 0.0652 (16) | −0.0010 (10) | −0.0056 (11) | −0.0037 (11) |
C13 | 0.0417 (13) | 0.0599 (15) | 0.0606 (15) | 0.0026 (11) | −0.0051 (11) | −0.0062 (12) |
C14 | 0.0386 (12) | 0.0548 (14) | 0.0615 (15) | 0.0028 (10) | −0.0023 (11) | −0.0094 (11) |
C15 | 0.0411 (13) | 0.0677 (16) | 0.0540 (14) | −0.0034 (11) | −0.0093 (11) | −0.0035 (12) |
C16 | 0.0453 (14) | 0.0749 (18) | 0.0596 (15) | −0.0038 (12) | −0.0036 (12) | −0.0055 (13) |
C17 | 0.0370 (12) | 0.0616 (15) | 0.0564 (15) | −0.0028 (11) | −0.0010 (11) | −0.0014 (12) |
C18 | 0.0451 (13) | 0.0548 (14) | 0.0541 (14) | 0.0052 (11) | −0.0032 (11) | 0.0044 (11) |
C19 | 0.0481 (13) | 0.0471 (13) | 0.0549 (14) | −0.0011 (11) | 0.0006 (11) | 0.0005 (11) |
C20 | 0.0364 (12) | 0.0562 (14) | 0.0544 (14) | −0.0015 (10) | −0.0005 (11) | 0.0044 (11) |
C21 | 0.0458 (14) | 0.0509 (15) | 0.0831 (19) | 0.0057 (11) | −0.0064 (13) | 0.0089 (13) |
C22 | 0.0499 (14) | 0.0490 (14) | 0.086 (2) | −0.0052 (12) | −0.0043 (14) | −0.0047 (13) |
C23 | 0.122 (3) | 0.0499 (16) | 0.0619 (18) | 0.0174 (16) | 0.0018 (17) | −0.0008 (13) |
C24 | 0.0581 (17) | 0.097 (2) | 0.076 (2) | 0.0129 (15) | −0.0156 (15) | 0.0192 (17) |
O1W | 0.104 (2) | 0.0987 (17) | 0.0698 (15) | −0.0214 (15) | −0.0146 (14) | 0.0143 (12) |
O2W | 0.1143 (19) | 0.0535 (12) | 0.0948 (18) | −0.0154 (12) | −0.0341 (15) | 0.0146 (12) |
O1—C4 | 1.366 (3) | C10—H10B | 0.9700 |
O1—C7 | 1.431 (3) | C11—C12 | 1.503 (3) |
O2—C5 | 1.365 (3) | C12—C13 | 1.525 (3) |
O2—C8 | 1.423 (3) | C12—H12A | 0.9700 |
O3—C11 | 1.233 (3) | C12—H12B | 0.9700 |
O4—C19 | 1.374 (3) | C13—C14 | 1.510 (3) |
O4—C23 | 1.419 (3) | C13—H13A | 0.9700 |
O5—C20 | 1.363 (3) | C13—H13B | 0.9700 |
O5—C24 | 1.427 (3) | C14—H14A | 0.9700 |
N1—C11 | 1.334 (3) | C14—H14B | 0.9700 |
N1—C10 | 1.449 (3) | C15—C16 | 1.521 (3) |
N1—H1 | 0.86 (2) | C15—H15A | 0.9700 |
N2—C15 | 1.488 (3) | C15—H15B | 0.9700 |
N2—C14 | 1.490 (3) | C16—C17 | 1.505 (3) |
N2—H2 | 0.92 (3) | C16—H16A | 0.9700 |
N2—H3 | 0.99 (3) | C16—H16B | 0.9700 |
C1—C2 | 1.377 (3) | C17—C22 | 1.369 (3) |
C1—C6 | 1.392 (3) | C17—C18 | 1.398 (3) |
C1—C9 | 1.512 (3) | C18—C19 | 1.375 (3) |
C2—C3 | 1.392 (3) | C18—H18A | 0.9300 |
C2—H2A | 0.9300 | C19—C20 | 1.404 (3) |
C3—C4 | 1.368 (3) | C20—C21 | 1.374 (3) |
C3—H3A | 0.9300 | C21—C22 | 1.380 (3) |
C4—C5 | 1.405 (3) | C21—H21A | 0.9300 |
C5—C6 | 1.373 (3) | C22—H22A | 0.9300 |
C6—H6A | 0.9300 | C23—H23A | 0.9600 |
C7—H7A | 0.9600 | C23—H23B | 0.9600 |
C7—H7B | 0.9600 | C23—H23C | 0.9600 |
C7—H7C | 0.9600 | C24—H24A | 0.9600 |
C8—H8A | 0.9600 | C24—H24B | 0.9600 |
C8—H8B | 0.9600 | C24—H24C | 0.9600 |
C8—H8C | 0.9600 | O1W—H1W1 | 0.86 (5) |
C9—C10 | 1.517 (3) | O1W—H2W1 | 0.91 (5) |
C9—H9A | 0.9700 | O2W—H1W2 | 0.96 (4) |
C9—H9B | 0.9700 | O2W—H2W2 | 0.80 (4) |
C10—H10A | 0.9700 | ||
C4—O1—C7 | 117.0 (2) | C13—C12—H12A | 109.4 |
C5—O2—C8 | 117.19 (19) | C11—C12—H12B | 109.4 |
C19—O4—C23 | 117.45 (19) | C13—C12—H12B | 109.4 |
C20—O5—C24 | 116.9 (2) | H12A—C12—H12B | 108.0 |
C11—N1—C10 | 122.6 (2) | C14—C13—C12 | 111.4 (2) |
C11—N1—H1 | 116.1 (16) | C14—C13—H13A | 109.3 |
C10—N1—H1 | 121.2 (16) | C12—C13—H13A | 109.3 |
C15—N2—C14 | 112.89 (19) | C14—C13—H13B | 109.3 |
C15—N2—H2 | 108.8 (16) | C12—C13—H13B | 109.3 |
C14—N2—H2 | 108.9 (16) | H13A—C13—H13B | 108.0 |
C15—N2—H3 | 108.8 (13) | N2—C14—C13 | 111.5 (2) |
C14—N2—H3 | 108.5 (14) | N2—C14—H14A | 109.3 |
H2—N2—H3 | 109 (2) | C13—C14—H14A | 109.3 |
C2—C1—C6 | 118.3 (2) | N2—C14—H14B | 109.3 |
C2—C1—C9 | 121.6 (2) | C13—C14—H14B | 109.3 |
C6—C1—C9 | 120.1 (2) | H14A—C14—H14B | 108.0 |
C1—C2—C3 | 120.0 (2) | N2—C15—C16 | 112.3 (2) |
C1—C2—H2A | 120.0 | N2—C15—H15A | 109.2 |
C3—C2—H2A | 120.0 | C16—C15—H15A | 109.2 |
C4—C3—C2 | 121.6 (2) | N2—C15—H15B | 109.2 |
C4—C3—H3A | 119.2 | C16—C15—H15B | 109.2 |
C2—C3—H3A | 119.2 | H15A—C15—H15B | 107.9 |
O1—C4—C3 | 125.7 (2) | C17—C16—C15 | 109.2 (2) |
O1—C4—C5 | 115.6 (2) | C17—C16—H16A | 109.8 |
C3—C4—C5 | 118.7 (2) | C15—C16—H16A | 109.8 |
O2—C5—C6 | 125.1 (2) | C17—C16—H16B | 109.8 |
O2—C5—C4 | 115.5 (2) | C15—C16—H16B | 109.8 |
C6—C5—C4 | 119.3 (2) | H16A—C16—H16B | 108.3 |
C5—C6—C1 | 122.0 (2) | C22—C17—C18 | 117.9 (2) |
C5—C6—H6A | 119.0 | C22—C17—C16 | 122.1 (2) |
C1—C6—H6A | 119.0 | C18—C17—C16 | 119.9 (2) |
O1—C7—H7A | 109.5 | C19—C18—C17 | 121.1 (2) |
O1—C7—H7B | 109.5 | C19—C18—H18A | 119.4 |
H7A—C7—H7B | 109.5 | C17—C18—H18A | 119.4 |
O1—C7—H7C | 109.5 | O4—C19—C18 | 124.6 (2) |
H7A—C7—H7C | 109.5 | O4—C19—C20 | 115.3 (2) |
H7B—C7—H7C | 109.5 | C18—C19—C20 | 120.1 (2) |
O2—C8—H8A | 109.5 | O5—C20—C21 | 125.5 (2) |
O2—C8—H8B | 109.5 | O5—C20—C19 | 116.0 (2) |
H8A—C8—H8B | 109.5 | C21—C20—C19 | 118.5 (2) |
O2—C8—H8C | 109.5 | C20—C21—C22 | 120.8 (2) |
H8A—C8—H8C | 109.5 | C20—C21—H21A | 119.6 |
H8B—C8—H8C | 109.5 | C22—C21—H21A | 119.6 |
C1—C9—C10 | 111.61 (19) | C17—C22—C21 | 121.6 (2) |
C1—C9—H9A | 109.3 | C17—C22—H22A | 119.2 |
C10—C9—H9A | 109.3 | C21—C22—H22A | 119.2 |
C1—C9—H9B | 109.3 | O4—C23—H23A | 109.5 |
C10—C9—H9B | 109.3 | O4—C23—H23B | 109.5 |
H9A—C9—H9B | 108.0 | H23A—C23—H23B | 109.5 |
N1—C10—C9 | 111.15 (19) | O4—C23—H23C | 109.5 |
N1—C10—H10A | 109.4 | H23A—C23—H23C | 109.5 |
C9—C10—H10A | 109.4 | H23B—C23—H23C | 109.5 |
N1—C10—H10B | 109.4 | O5—C24—H24A | 109.5 |
C9—C10—H10B | 109.4 | O5—C24—H24B | 109.5 |
H10A—C10—H10B | 108.0 | H24A—C24—H24B | 109.5 |
O3—C11—N1 | 121.3 (2) | O5—C24—H24C | 109.5 |
O3—C11—C12 | 122.0 (2) | H24A—C24—H24C | 109.5 |
N1—C11—C12 | 116.7 (2) | H24B—C24—H24C | 109.5 |
C11—C12—C13 | 111.3 (2) | H1W1—O1W—H2W1 | 111 (4) |
C11—C12—H12A | 109.4 | H1W2—O2W—H2W2 | 113 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl1i | 0.87 (2) | 2.44 (2) | 3.300 (2) | 173 (2) |
O2W—H1W2···O3 | 0.95 (5) | 1.75 (5) | 2.704 (3) | 179 (6) |
N2—H2···Cl1 | 0.92 (3) | 2.22 (3) | 3.127 (2) | 169 (3) |
O2W—H2W2···O1Wii | 0.80 (4) | 1.97 (4) | 2.767 (4) | 171 (4) |
N2—H3···O2Wiii | 0.99 (2) | 1.72 (2) | 2.709 (3) | 177 (2) |
O1W—H1W1···Cl1i | 0.87 (5) | 2.31 (5) | 3.177 (3) | 177 (6) |
O1W—H2W1···Cl1 | 0.91 (4) | 2.31 (4) | 3.194 (4) | 164 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z+1/2; (iii) −x+1, −y+2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl1i | 0.87 (2) | 2.44 (2) | 3.300 (2) | 173 (2) |
O2W—H1W2···O3 | 0.95 (5) | 1.75 (5) | 2.704 (3) | 179 (6) |
N2—H2···Cl1 | 0.92 (3) | 2.22 (3) | 3.127 (2) | 169 (3) |
O2W—H2W2···O1Wii | 0.80 (4) | 1.97 (4) | 2.767 (4) | 171 (4) |
N2—H3···O2Wiii | 0.99 (2) | 1.72 (2) | 2.709 (3) | 177 (2) |
O1W—H1W1···Cl1i | 0.87 (5) | 2.31 (5) | 3.177 (3) | 177 (6) |
O1W—H2W1···Cl1 | 0.91 (4) | 2.31 (4) | 3.194 (4) | 164 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z+1/2; (iii) −x+1, −y+2, −z+1. |
Acknowledgements
We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study (grant FA–F7–T185).
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The title compound, C24H35N2O5+.Cl-(H2O)2, was isolated as an intermediate product in the synthesis of isoquinoline alkaloid analogues (Saidov et al., 2013). Similar compounds have been synthesized (Bentley, 2006), or their structures characterized (Peters et al., 1994).
A perspective view of the moleculular entities of the title compound, showing the atomic numbering scheme, is given in Fig. 1. Bond lengths and angles are in normal ranges (Allen et al., 1987). The organic molecule contains two N atoms, amidic and aminic. The N atom on an amide is usually less nucleophilic than the N atom of an amine, due to the resonance stabilization of the N atom lone-pair provided by the amide carbonyl group. Therefore, in the cation the protonization of the amino N atom is observed.
In the crystal structure, two chloride anion and one lattice water molecule form a centrosymmetric four-membered hydrogen-bonding cycle (Fig. 2). The protonated organic molecules are bridged by N—H···Cl and C═O···H—O(w) hydrogen bonds (Table 1). As a result, hydrogen-bonded layers parallel to (100) are formed that have a thickness corresponding to the length of the a axis.