[2-(3,4-Di­meth­oxy­phen­yl)eth­yl](3-{N-[2-(3,4-di­meth­oxy­phen­yl)eth­yl]carbamo­yl}prop­yl)aza­nium chloride dihydrate

Saidov, A.S.; Turgunov, K.K.

doi:10.1107/S1600536814001998

organic compounds

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ISSN: 2056-9890

Volume 70| Part 2| February 2014| Page o232

doi:10.1107/S1600536814001998

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[2-(3,4-Dimethoxyphenyl)ethyl](3-{N-[2-(3,4-dimethoxyphenyl)ethyl]carbamoyl}propyl)azanium chloride dihydrate

Abdusalom Sh. Saidov ^a ^* and Kambarali K. Turgunov ^a

^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

(Received 23 January 2014; accepted 28 January 2014; online 31 January 2014)

The asymmetric unit of the title hydrated salt, C₂₄H₃₅N₂O₅⁺·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].

CCDC 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 crystal structure of a related compound, see: Peters et al. (1994 ).

Experimental

Crystal data

C₂₄H₃₅N₂O₅⁺·Cl⁻·2H₂O
M_r = 503.02
Monoclinic, P 2₁ /c
a = 21.977 (3) Å
b = 12.2295 (10) Å
c = 10.2217 (9) Å
β = 93.490 (9)°
V = 2742.2 (5) Å³
Z = 4
Cu Kα radiation
μ = 1.59 mm⁻¹
T = 295 K
0.60 × 0.40 × 0.35 mm

Data collection

Oxford Diffraction Xcalibur Ruby diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.599, T_max = 1.000
11225 measured reflections
4860 independent reflections
3012 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.131
S = 0.97
4860 reflections
339 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+2, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: 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

Crystal structure: contains datablocks I, GLOBAL. DOI: 10.1107/S1600536814001998/wm2799sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814001998/wm2799Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814001998/wm2799Isup3.cml

checkCIF report

Comment top

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.

Related literature top

For standard bond lengths, see: Allen et al. (1987). For the synthesis of related compounds, see: Bentley (2006); Saidov et al. (2013). For the crystal structure of a related compound, see: Peters et al. (1994).

Experimental top

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 R_f 0.9, 0.5 and 0.2 (title compound) (chloroform:methanol=8:1). The compounds were isolated by column chromatography (silica gel); 0.075 g of the title compound were obtained with a m.p. 406-408 K. IR (KBr, ν, cm^-1): 3434, 3258, 2940, 1651, 1590, 1519. Crystals suitable for X-ray diffraction analysis were obtained from a chloroform–methanol (8:1) mixture by slow evaporation.

Structure description top

For standard bond lengths, see: Allen et al. (1987). For the synthesis of related compounds, see: Bentley (2006); Saidov et al. (2013). For the crystal structure of a related compound, see: Peters et al. (1994).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: 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).

Figures top

	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)

[2-(3,4-Dimethoxyphenyl)ethyl](3-{N-[2-(3,4-dimethoxyphenyl)ethyl]carbamoyl}propyl)azanium chloride dihydrate top

Crystal data top

C₂₄H₃₅N₂O₅⁺·Cl⁻·2H₂O	F(000) = 1080
M_r = 503.02	D_x = 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

Data collection top

Oxford Diffraction Xcalibur Ruby diffractometer	4860 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3012 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 10.2576 pixels mm^-1	θ_max = 67.3°, θ_min = 4.0°
ω scans	h = −25→26
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −14→12
T_min = 0.599, T_max = 1.000	l = −12→12
11225 measured reflections

Refinement top

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(F_o²) + (0.0748P)²] where P = (F_o² + 2F_c²)/3
4860 reflections	(Δ/σ)_max = 0.001
339 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₄H₃₅N₂O₅⁺·Cl⁻·2H₂O	V = 2742.2 (5) Å³
M_r = 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)°

Data collection top

Oxford Diffraction Xcalibur Ruby diffractometer	4860 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	3012 reflections with I > 2σ(I)
T_min = 0.599, T_max = 1.000	R_int = 0.035
11225 measured reflections

Refinement top

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	Δρ_max = 0.20 e Å⁻³
4860 reflections	Δρ_min = −0.24 e Å⁻³
339 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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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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Volume 70| Part 2| February 2014| Page o232

doi:10.1107/S1600536814001998

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

[2-(3,4-Di­meth­­oxy­phen­yl)eth­yl](3-{N-[2-(3,4-di­meth­­oxy­phen­yl)eth­yl]carbamo­yl}prop­yl)aza­nium chloride dihydrate

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Experimental

Crystal data

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organic compounds

[2-(3,4-Dimethoxyphenyl)ethyl](3-{N-[2-(3,4-dimethoxyphenyl)ethyl]carbamoyl}propyl)azanium chloride dihydrate