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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

N′-[(2-n-Butyl-4-chloro-1H-imidazol-5-yl)­methyl­­idene]adamantane-1-carbo­hydrazide sesquihydrate ethanol hemi­solvate

aDepartment of Pharmaceutical Chemistry, College of Chemistry, King Saud University, Riyadh 11451, Saudi Arabia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 20 July 2010; accepted 22 July 2010; online 31 July 2010)

In the asymmetric unit of the title compound, C19H27ClN4O·0.5C2H6O·1.5H2O, there are two mol­ecules of the Schiff base, which has a rigid adamantyl cage at one end of the C(= O)NH–N=CH– chain and an almost planar [torsion angles = 1.3 (1) and 7.9 (2)° imidazolyl ring at the other end, three mol­ecules of water and one mol­ecule of ethanol. In both independent mol­ecules of the Schiff base, this chain displays an extended zigzag configuration. All their amino groups function as hydrogen-bond donors to water mol­ecules; these are linked to other acceptor atoms, generating a layer structure. O—H⋯O and O—H⋯N inter­actions involving the water mol­ecules also occur.

Related literature

For the cyclization of this class of Schiff bases to pharmaceutically useful chemicals, see: Kadi et al. (2007[Kadi, A. A., El-Brollosy, N. R., Al-Deeb, O. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2007). Eur. J. Med. Chem. 42, 235-242.]).

[Scheme 1]

Experimental

Crystal data
  • C19H27ClN4O·0.5C2H6O·1.5H2O

  • Mr = 412.95

  • Triclinic, [P \overline 1]

  • a = 7.9867 (6) Å

  • b = 16.8478 (13) Å

  • c = 16.9656 (13) Å

  • α = 97.341 (1)°

  • β = 100.376 (1)°

  • γ = 97.505 (1)°

  • V = 2199.3 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.20 mm−1

  • T = 100 K

  • 0.40 × 0.10 × 0.10 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.924, Tmax = 0.980

  • 21291 measured reflections

  • 10050 independent reflections

  • 7547 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.113

  • S = 1.02

  • 10050 reflections

  • 552 parameters

  • 11 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.43 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O3i 0.86 (1) 2.00 (1) 2.841 (2) 166 (2)
N3—H3⋯O1wii 0.86 (1) 1.95 (1) 2.806 (2) 170 (2)
N6—H6⋯O2w 0.88 (1) 1.95 (1) 2.829 (2) 174 (2)
N8—H8⋯O3wiii 0.86 (1) 1.94 (1) 2.778 (2) 164 (2)
O3—H3o⋯O1w 0.84 (1) 1.84 (1) 2.673 (2) 177 (2)
O1w—H11⋯O1ii 0.84 (1) 2.00 (1) 2.821 (2) 166 (2)
O1w—H12⋯N5 0.84 (1) 1.91 (1) 2.751 (2) 175 (3)
O2w—H21⋯O2 0.85 (1) 2.07 (1) 2.905 (2) 172 (2)
O2w—H22⋯O2iv 0.84 (1) 1.93 (1) 2.764 (2) 176 (2)
O3w—H31⋯N4 0.84 (1) 1.94 (1) 2.773 (2) 169 (2)
O3w—H32⋯O2w 0.85 (1) 1.92 (1) 2.766 (2) 174 (2)
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) -x+1, -y+2, -z+1; (iii) x+1, y, z; (iv) -x+1, -y+2, -z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Adamantane-1-carbohydrazide is a commercially available compound that condenses with primary amines to form Schiff bases; some of these Schiff bases can be cyclized to yield pharmaceutically useful compounds (Kadi et al., 2007). However, unlike other aryolhydrazides, there have been no reports of the crystal structures of these Schiff bases. The condensation product with 2-n-butyl-5-chloro-1H-imidazole-4-carboxaldehyde crystallizes from aqueous ethanol as a sesquihydrate hemiethanol solvate (Scheme 1). There are two independent Schiff base molecules in the asymmetric unit (Fig. 1). The molecule of C20H27ClN4O has a rigid adamantyl cage at one end of the C( O)NH–NCH– chain and a planar imidazolyl ring at the other end; the chain displays an extended zigzag configuration.

The amino groups all function as hydrogen-bond donors to water molecules; these are linked to other acceptor atoms to generate a layer structure (Fig. 2).

Related literature top

For the cyclization of this class of Schiff bases to pharmaceutically useful chemicals, see: Kadi et al. (2007).

Experimental top

Adamantane-1-carbohydrazide (1.94 g, 1 mmol) and 2-n-butyl-5-chloro-1H-imidazole-4-carboxaldehyde (1.87 g, 1 mmol) were heated in ethanol (50 ml) for 1 h. The solvent was removed and the product recrystallized from aqueous ethanol to afford colorless primatic crystals in 90% yield.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C).

The amino and water H-atoms were located in a difference Fourier map, and were refined isotropically with distance restraints of N–H 0.86±0.01 Å and O–H 0.84±0.01 Å.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Anisotropic ellipsoid plot (Barbour, 2001) of C19H27ClN4O.0.5C2H5OH.1.5H2O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
[Figure 2] Fig. 2. Hydrogen-bonded layer structure.
N'-[(2-n-Butyl-4-chloro-1H-imidazol-5- yl)methylidene]adamantane-1-carbohydrazide sesquihydrate ethanol hemisolvate top
Crystal data top
C19H27ClN4O·0.5C2H6O·1.5H2OZ = 4
Mr = 412.95F(000) = 888
Triclinic, P1Dx = 1.247 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.9867 (6) ÅCell parameters from 4692 reflections
b = 16.8478 (13) Åθ = 2.5–28.2°
c = 16.9656 (13) ŵ = 0.20 mm1
α = 97.341 (1)°T = 100 K
β = 100.376 (1)°Prism, colorless
γ = 97.505 (1)°0.40 × 0.10 × 0.10 mm
V = 2199.3 (3) Å3
Data collection top
Bruker SMART APEX
diffractometer
10050 independent reflections
Radiation source: fine-focus sealed tube7547 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.924, Tmax = 0.980k = 2221
21291 measured reflectionsl = 2121
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0579P)2]
where P = (Fo2 + 2Fc2)/3
10050 reflections(Δ/σ)max = 0.001
552 parametersΔρmax = 0.37 e Å3
11 restraintsΔρmin = 0.43 e Å3
Crystal data top
C19H27ClN4O·0.5C2H6O·1.5H2Oγ = 97.505 (1)°
Mr = 412.95V = 2199.3 (3) Å3
Triclinic, P1Z = 4
a = 7.9867 (6) ÅMo Kα radiation
b = 16.8478 (13) ŵ = 0.20 mm1
c = 16.9656 (13) ÅT = 100 K
α = 97.341 (1)°0.40 × 0.10 × 0.10 mm
β = 100.376 (1)°
Data collection top
Bruker SMART APEX
diffractometer
10050 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
7547 reflections with I > 2σ(I)
Tmin = 0.924, Tmax = 0.980Rint = 0.036
21291 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04311 restraints
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.37 e Å3
10050 reflectionsΔρmin = 0.43 e Å3
552 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.76837 (6)1.16482 (3)0.27186 (3)0.02855 (12)
Cl20.96970 (5)0.80656 (2)0.35728 (3)0.02268 (10)
O10.75877 (14)1.40939 (7)0.65640 (7)0.0201 (3)
O20.73265 (14)1.07788 (7)0.06758 (7)0.0188 (2)
O30.78300 (16)0.63333 (8)0.50491 (8)0.0284 (3)
O1W0.54116 (15)0.70102 (7)0.41892 (7)0.0196 (3)
O2W0.46191 (15)0.95403 (7)0.08834 (7)0.0201 (3)
O3W0.27823 (15)1.00424 (7)0.20395 (7)0.0216 (3)
N10.92004 (18)1.38006 (8)0.56315 (8)0.0180 (3)
N20.78186 (17)1.32710 (8)0.51751 (8)0.0178 (3)
N30.50609 (18)1.21097 (8)0.43693 (8)0.0173 (3)
N40.46659 (18)1.13115 (8)0.31913 (8)0.0204 (3)
N50.62851 (18)0.77835 (8)0.29533 (8)0.0195 (3)
N60.60000 (18)0.86304 (8)0.20631 (8)0.0176 (3)
N70.83450 (17)0.98033 (8)0.16998 (8)0.0158 (3)
N80.95038 (17)1.04002 (8)0.15190 (8)0.0151 (3)
C11.0617 (2)1.46542 (9)0.69156 (9)0.0157 (3)
C21.1519 (2)1.52998 (9)0.64919 (10)0.0182 (3)
H2A1.18531.50320.60020.022*
H2B1.07161.56750.63210.022*
C31.3131 (2)1.57772 (10)0.70820 (10)0.0214 (4)
H3A1.37061.61980.68110.026*
C41.4376 (2)1.51865 (11)0.73189 (11)0.0238 (4)
H4A1.47081.49210.68280.029*
H4B1.54351.54870.76880.029*
C51.3512 (2)1.45452 (10)0.77393 (10)0.0218 (4)
H51.43301.41640.78950.026*
C61.3012 (2)1.49608 (11)0.85039 (10)0.0250 (4)
H6A1.24651.45480.87830.030*
H6B1.40571.52640.88810.030*
C71.1755 (2)1.55423 (10)0.82642 (10)0.0218 (4)
H71.14281.58130.87620.026*
C81.2614 (2)1.61865 (10)0.78384 (11)0.0249 (4)
H8A1.18031.65630.76840.030*
H8B1.36481.65040.82130.030*
C91.1886 (2)1.40708 (10)0.71633 (10)0.0184 (3)
H9A1.13291.36540.74350.022*
H9B1.22031.37930.66740.022*
C101.0134 (2)1.50723 (10)0.76836 (10)0.0183 (3)
H10A0.93191.54490.75340.022*
H10B0.95591.46610.79560.022*
C110.8996 (2)1.41698 (9)0.63612 (9)0.0153 (3)
C120.8028 (2)1.28451 (9)0.45310 (9)0.0173 (3)
H12A0.90931.29090.43540.021*
C130.6573 (2)1.22641 (9)0.40851 (10)0.0165 (3)
C140.6272 (2)1.17570 (10)0.33610 (10)0.0185 (3)
C150.3969 (2)1.15408 (10)0.38198 (10)0.0198 (4)
C160.2199 (2)1.11990 (11)0.39062 (11)0.0251 (4)
H16A0.14251.10940.33660.030*
H16B0.17591.16050.42560.030*
C170.2146 (2)1.04091 (11)0.42715 (12)0.0308 (4)
H17A0.09401.01270.41580.037*
H17B0.28331.00510.40030.037*
C180.2832 (3)1.05454 (13)0.51753 (13)0.0377 (5)
H18A0.21491.09070.54430.045*
H18B0.40391.08250.52870.045*
C190.2776 (3)0.97727 (16)0.55442 (17)0.0588 (8)
H19A0.31890.99060.61330.088*
H19B0.35150.94260.53110.088*
H19C0.15890.94860.54280.088*
C201.0200 (2)1.15241 (9)0.07997 (9)0.0143 (3)
C211.1515 (2)1.19510 (10)0.15687 (9)0.0173 (3)
H21A1.09031.22150.19620.021*
H21B1.21211.15460.18270.021*
C221.2828 (2)1.25884 (10)0.13452 (10)0.0191 (4)
H22A1.36721.28600.18460.023*
C231.1891 (2)1.32202 (10)0.09564 (11)0.0239 (4)
H23A1.12751.34910.13440.029*
H23B1.27361.36370.08180.029*
C241.0604 (2)1.28048 (10)0.01893 (11)0.0233 (4)
H240.99921.32180.00640.028*
C250.9281 (2)1.21643 (10)0.04083 (11)0.0201 (4)
H25A0.86451.24290.07900.024*
H25B0.84391.19000.00880.024*
C261.1560 (2)1.23945 (11)0.04119 (11)0.0259 (4)
H26A1.07301.21300.09110.031*
H26B1.24021.28050.05620.031*
C271.2497 (2)1.17624 (10)0.00257 (10)0.0206 (4)
H271.31251.14960.04190.025*
C281.3788 (2)1.21725 (10)0.07450 (10)0.0216 (4)
H28A1.46571.25790.06070.026*
H28B1.43951.17630.09960.026*
C291.1182 (2)1.11208 (9)0.01915 (10)0.0181 (3)
H29A1.17841.07060.04350.022*
H29B1.03551.08490.03060.022*
C300.8874 (2)1.08749 (9)0.09866 (9)0.0147 (3)
C310.8957 (2)0.93466 (9)0.21920 (9)0.0170 (3)
H31A1.01570.94050.24100.020*
C320.7734 (2)0.87396 (9)0.23988 (9)0.0168 (3)
C330.7857 (2)0.82064 (10)0.29406 (10)0.0182 (3)
C340.5179 (2)0.80624 (10)0.24081 (10)0.0188 (3)
C350.3269 (2)0.77994 (10)0.21929 (11)0.0235 (4)
H35A0.27610.81350.18040.028*
H35B0.27860.78980.26880.028*
C360.2740 (2)0.69046 (10)0.18198 (10)0.0223 (4)
H36A0.31370.65690.22330.027*
H36B0.14660.67820.16800.027*
C370.3442 (2)0.66585 (11)0.10660 (11)0.0273 (4)
H37A0.47170.67400.12090.033*
H37B0.31060.70110.06600.033*
C380.2775 (3)0.57763 (13)0.06950 (12)0.0390 (5)
H38A0.32920.56360.02240.058*
H38B0.15180.57000.05230.058*
H38C0.30850.54260.10990.058*
C390.7041 (2)0.59637 (11)0.56315 (11)0.0292 (4)
H39A0.74160.54310.56760.035*
H39B0.57730.58710.54460.035*
C400.7512 (3)0.64869 (12)0.64503 (11)0.0317 (4)
H40A0.70630.61930.68500.048*
H40B0.70110.69860.64230.048*
H40C0.87690.66230.66110.048*
H3o0.709 (2)0.6547 (12)0.4769 (11)0.040 (6)*
H110.4462 (17)0.6699 (11)0.4039 (12)0.039 (6)*
H120.561 (3)0.7241 (15)0.3798 (11)0.068 (9)*
H210.547 (2)0.9885 (11)0.0863 (14)0.047 (7)*
H220.402 (2)0.9418 (11)0.0416 (7)0.028 (5)*
H310.348 (2)1.0401 (11)0.2379 (11)0.050 (7)*
H320.328 (3)0.9889 (13)0.1658 (10)0.047 (7)*
H11.0165 (16)1.3843 (11)0.5468 (11)0.022 (5)*
H30.491 (2)1.2324 (11)0.4835 (7)0.030 (5)*
H60.553 (2)0.8878 (11)0.1671 (9)0.032 (6)*
H81.0584 (13)1.0385 (11)0.1682 (11)0.029 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0305 (3)0.0324 (2)0.0219 (2)0.00006 (19)0.01191 (19)0.00352 (18)
Cl20.0199 (2)0.0231 (2)0.0234 (2)0.00125 (16)0.00039 (17)0.00668 (16)
O10.0146 (6)0.0253 (6)0.0187 (6)0.0019 (5)0.0044 (5)0.0003 (5)
O20.0139 (6)0.0229 (6)0.0171 (6)0.0021 (5)0.0006 (5)0.0038 (5)
O30.0208 (7)0.0456 (8)0.0228 (7)0.0111 (6)0.0065 (6)0.0107 (6)
O1W0.0161 (6)0.0242 (6)0.0177 (6)0.0031 (5)0.0048 (5)0.0044 (5)
O2W0.0151 (6)0.0263 (7)0.0163 (6)0.0022 (5)0.0003 (5)0.0045 (5)
O3W0.0147 (6)0.0240 (6)0.0226 (7)0.0009 (5)0.0018 (5)0.0030 (5)
N10.0125 (7)0.0218 (7)0.0166 (7)0.0038 (6)0.0030 (6)0.0012 (6)
N20.0152 (7)0.0191 (7)0.0162 (7)0.0024 (5)0.0006 (6)0.0007 (5)
N30.0159 (7)0.0194 (7)0.0155 (7)0.0012 (6)0.0029 (6)0.0009 (6)
N40.0193 (8)0.0203 (7)0.0191 (7)0.0003 (6)0.0003 (6)0.0012 (6)
N50.0180 (7)0.0199 (7)0.0211 (7)0.0002 (6)0.0058 (6)0.0052 (6)
N60.0143 (7)0.0188 (7)0.0197 (7)0.0002 (6)0.0036 (6)0.0053 (6)
N70.0151 (7)0.0164 (7)0.0146 (7)0.0035 (5)0.0047 (5)0.0010 (5)
N80.0111 (7)0.0167 (7)0.0159 (7)0.0026 (5)0.0021 (5)0.0029 (5)
C10.0137 (8)0.0160 (8)0.0161 (8)0.0000 (6)0.0015 (6)0.0015 (6)
C20.0155 (8)0.0178 (8)0.0210 (8)0.0000 (6)0.0035 (7)0.0047 (7)
C30.0157 (8)0.0199 (8)0.0259 (9)0.0040 (7)0.0034 (7)0.0018 (7)
C40.0138 (8)0.0291 (9)0.0248 (9)0.0008 (7)0.0008 (7)0.0030 (7)
C50.0185 (9)0.0260 (9)0.0191 (9)0.0073 (7)0.0019 (7)0.0011 (7)
C60.0248 (10)0.0287 (9)0.0175 (9)0.0023 (8)0.0011 (7)0.0017 (7)
C70.0182 (9)0.0241 (9)0.0202 (9)0.0012 (7)0.0033 (7)0.0049 (7)
C80.0185 (9)0.0193 (8)0.0313 (10)0.0011 (7)0.0010 (8)0.0042 (7)
C90.0188 (9)0.0167 (8)0.0182 (8)0.0019 (6)0.0012 (7)0.0010 (6)
C100.0169 (8)0.0191 (8)0.0175 (8)0.0008 (7)0.0037 (7)0.0011 (6)
C110.0165 (8)0.0144 (7)0.0156 (8)0.0017 (6)0.0038 (6)0.0042 (6)
C120.0154 (8)0.0193 (8)0.0169 (8)0.0000 (6)0.0045 (7)0.0034 (6)
C130.0147 (8)0.0184 (8)0.0171 (8)0.0027 (6)0.0038 (6)0.0040 (6)
C140.0198 (9)0.0208 (8)0.0150 (8)0.0022 (7)0.0039 (7)0.0032 (6)
C150.0170 (9)0.0197 (8)0.0207 (9)0.0015 (7)0.0001 (7)0.0030 (7)
C160.0147 (9)0.0299 (10)0.0275 (10)0.0006 (7)0.0004 (7)0.0021 (8)
C170.0235 (10)0.0261 (10)0.0420 (12)0.0028 (8)0.0130 (9)0.0003 (8)
C180.0370 (12)0.0422 (12)0.0415 (12)0.0121 (10)0.0177 (10)0.0152 (10)
C190.0459 (15)0.0676 (17)0.088 (2)0.0273 (13)0.0378 (14)0.0514 (16)
C200.0138 (8)0.0145 (7)0.0128 (7)0.0010 (6)0.0009 (6)0.0010 (6)
C210.0155 (8)0.0184 (8)0.0151 (8)0.0037 (6)0.0021 (6)0.0004 (6)
C220.0159 (8)0.0181 (8)0.0192 (8)0.0048 (6)0.0016 (7)0.0015 (6)
C230.0231 (9)0.0150 (8)0.0320 (10)0.0036 (7)0.0092 (8)0.0007 (7)
C240.0201 (9)0.0187 (8)0.0302 (10)0.0001 (7)0.0007 (8)0.0098 (7)
C250.0159 (8)0.0188 (8)0.0255 (9)0.0022 (7)0.0027 (7)0.0057 (7)
C260.0273 (10)0.0272 (9)0.0201 (9)0.0100 (8)0.0039 (8)0.0077 (7)
C270.0206 (9)0.0203 (8)0.0203 (9)0.0026 (7)0.0104 (7)0.0014 (7)
C280.0162 (8)0.0215 (8)0.0267 (9)0.0025 (7)0.0074 (7)0.0031 (7)
C290.0191 (9)0.0168 (8)0.0168 (8)0.0000 (6)0.0048 (7)0.0020 (6)
C300.0155 (8)0.0148 (7)0.0120 (7)0.0001 (6)0.0025 (6)0.0013 (6)
C310.0157 (8)0.0186 (8)0.0150 (8)0.0015 (6)0.0028 (6)0.0008 (6)
C320.0162 (8)0.0182 (8)0.0142 (8)0.0006 (6)0.0017 (6)0.0007 (6)
C330.0177 (8)0.0190 (8)0.0175 (8)0.0016 (7)0.0032 (7)0.0026 (6)
C340.0188 (9)0.0177 (8)0.0207 (8)0.0005 (7)0.0074 (7)0.0035 (7)
C350.0183 (9)0.0240 (9)0.0292 (10)0.0001 (7)0.0077 (7)0.0080 (7)
C360.0183 (9)0.0238 (9)0.0248 (9)0.0013 (7)0.0040 (7)0.0085 (7)
C370.0262 (10)0.0362 (10)0.0208 (9)0.0086 (8)0.0015 (8)0.0095 (8)
C380.0404 (13)0.0435 (12)0.0278 (11)0.0141 (10)0.0064 (9)0.0027 (9)
C390.0210 (10)0.0311 (10)0.0358 (11)0.0006 (8)0.0022 (8)0.0149 (8)
C400.0294 (11)0.0440 (12)0.0294 (10)0.0146 (9)0.0119 (8)0.0166 (9)
Geometric parameters (Å, º) top
Cl1—C141.7142 (17)C16—C171.537 (3)
Cl2—C331.7186 (17)C16—H16A0.9900
O1—C111.2300 (19)C16—H16B0.9900
O2—C301.2344 (19)C17—C181.510 (3)
O3—C391.428 (2)C17—H17A0.9900
O3—H3o0.84 (1)C17—H17B0.9900
O1W—H110.84 (1)C18—C191.514 (3)
O1W—H120.84 (1)C18—H18A0.9900
O2W—H210.85 (1)C18—H18B0.9900
O2W—H220.84 (1)C19—H19A0.9800
O3W—H310.84 (1)C19—H19B0.9800
O3W—H320.85 (1)C19—H19C0.9800
N1—C111.360 (2)C20—C301.525 (2)
N1—N21.3682 (18)C20—C251.535 (2)
N1—H10.86 (1)C20—C211.547 (2)
N2—C121.278 (2)C20—C291.547 (2)
N3—C151.345 (2)C21—C221.533 (2)
N3—C131.385 (2)C21—H21A0.9900
N3—H30.86 (1)C21—H21B0.9900
N4—C151.327 (2)C22—C231.529 (2)
N4—C141.361 (2)C22—C281.535 (2)
N5—C341.335 (2)C22—H22A1.0000
N5—C331.366 (2)C23—C241.529 (2)
N6—C341.344 (2)C23—H23A0.9900
N6—C321.378 (2)C23—H23B0.9900
N6—H60.88 (1)C24—C261.529 (3)
N7—C311.282 (2)C24—C251.538 (2)
N7—N81.3784 (18)C24—H241.0000
N8—C301.354 (2)C25—H25A0.9900
N8—H80.86 (1)C25—H25B0.9900
C1—C111.522 (2)C26—C271.527 (2)
C1—C101.536 (2)C26—H26A0.9900
C1—C91.544 (2)C26—H26B0.9900
C1—C21.549 (2)C27—C281.532 (2)
C2—C31.538 (2)C27—C291.533 (2)
C2—H2A0.9900C27—H271.0000
C2—H2B0.9900C28—H28A0.9900
C3—C81.527 (2)C28—H28B0.9900
C3—C41.536 (2)C29—H29A0.9900
C3—H3A1.0000C29—H29B0.9900
C4—C51.527 (2)C31—C321.441 (2)
C4—H4A0.9900C31—H31A0.9500
C4—H4B0.9900C32—C331.365 (2)
C5—C91.534 (2)C34—C351.496 (2)
C5—C61.536 (2)C35—C361.531 (2)
C5—H51.0000C35—H35A0.9900
C6—C71.531 (2)C35—H35B0.9900
C6—H6A0.9900C36—C371.519 (2)
C6—H6B0.9900C36—H36A0.9900
C7—C101.532 (2)C36—H36B0.9900
C7—C81.535 (2)C37—C381.524 (3)
C7—H71.0000C37—H37A0.9900
C8—H8A0.9900C37—H37B0.9900
C8—H8B0.9900C38—H38A0.9800
C9—H9A0.9900C38—H38B0.9800
C9—H9B0.9900C38—H38C0.9800
C10—H10A0.9900C39—C401.503 (3)
C10—H10B0.9900C39—H39A0.9900
C12—C131.441 (2)C39—H39B0.9900
C12—H12A0.9500C40—H40A0.9800
C13—C141.367 (2)C40—H40B0.9800
C15—C161.494 (2)C40—H40C0.9800
C39—O3—H3o108.2 (15)H19A—C19—H19B109.5
H11—O1W—H12108 (2)C18—C19—H19C109.5
H21—O2W—H22107 (2)H19A—C19—H19C109.5
H31—O3W—H32109 (2)H19B—C19—H19C109.5
C11—N1—N2116.73 (13)C30—C20—C25109.75 (13)
C11—N1—H1124.0 (13)C30—C20—C21112.26 (12)
N2—N1—H1119.0 (12)C25—C20—C21108.69 (13)
C12—N2—N1118.29 (14)C30—C20—C29108.65 (12)
C15—N3—C13107.94 (14)C25—C20—C29108.58 (13)
C15—N3—H3127.7 (13)C21—C20—C29108.83 (13)
C13—N3—H3124.2 (13)C22—C21—C20110.09 (13)
C15—N4—C14104.80 (13)C22—C21—H21A109.6
C34—N5—C33104.56 (13)C20—C21—H21A109.6
C34—N6—C32108.41 (14)C22—C21—H21B109.6
C34—N6—H6126.6 (13)C20—C21—H21B109.6
C32—N6—H6125.0 (13)H21A—C21—H21B108.2
C31—N7—N8116.86 (14)C23—C22—C28109.68 (14)
C30—N8—N7117.28 (13)C23—C22—C21109.51 (14)
C30—N8—H8124.6 (13)C28—C22—C21109.28 (13)
N7—N8—H8117.2 (13)C23—C22—H22A109.5
C11—C1—C10109.09 (13)C28—C22—H22A109.5
C11—C1—C9109.09 (12)C21—C22—H22A109.5
C10—C1—C9108.73 (13)C24—C23—C22109.42 (13)
C11—C1—C2111.73 (13)C24—C23—H23A109.8
C10—C1—C2109.51 (13)C22—C23—H23A109.8
C9—C1—C2108.64 (13)C24—C23—H23B109.8
C3—C2—C1109.50 (13)C22—C23—H23B109.8
C3—C2—H2A109.8H23A—C23—H23B108.2
C1—C2—H2A109.8C23—C24—C26109.71 (14)
C3—C2—H2B109.8C23—C24—C25109.66 (14)
C1—C2—H2B109.8C26—C24—C25109.38 (14)
H2A—C2—H2B108.2C23—C24—H24109.4
C8—C3—C4109.85 (14)C26—C24—H24109.4
C8—C3—C2109.70 (14)C25—C24—H24109.4
C4—C3—C2108.74 (13)C20—C25—C24110.06 (13)
C8—C3—H3A109.5C20—C25—H25A109.6
C4—C3—H3A109.5C24—C25—H25A109.6
C2—C3—H3A109.5C20—C25—H25B109.6
C5—C4—C3109.80 (14)C24—C25—H25B109.6
C5—C4—H4A109.7H25A—C25—H25B108.2
C3—C4—H4A109.7C27—C26—C24109.48 (14)
C5—C4—H4B109.7C27—C26—H26A109.8
C3—C4—H4B109.7C24—C26—H26A109.8
H4A—C4—H4B108.2C27—C26—H26B109.8
C4—C5—C9109.74 (13)C24—C26—H26B109.8
C4—C5—C6109.39 (14)H26A—C26—H26B108.2
C9—C5—C6109.32 (14)C26—C27—C28109.75 (14)
C4—C5—H5109.5C26—C27—C29109.49 (14)
C9—C5—H5109.5C28—C27—C29109.40 (13)
C6—C5—H5109.5C26—C27—H27109.4
C7—C6—C5109.40 (14)C28—C27—H27109.4
C7—C6—H6A109.8C29—C27—H27109.4
C5—C6—H6A109.8C27—C28—C22109.47 (13)
C7—C6—H6B109.8C27—C28—H28A109.8
C5—C6—H6B109.8C22—C28—H28A109.8
H6A—C6—H6B108.2C27—C28—H28B109.8
C6—C7—C10109.82 (14)C22—C28—H28B109.8
C6—C7—C8109.62 (14)H28A—C28—H28B108.2
C10—C7—C8108.98 (14)C27—C29—C20109.95 (12)
C6—C7—H7109.5C27—C29—H29A109.7
C10—C7—H7109.5C20—C29—H29A109.7
C8—C7—H7109.5C27—C29—H29B109.7
C3—C8—C7109.75 (13)C20—C29—H29B109.7
C3—C8—H8A109.7H29A—C29—H29B108.2
C7—C8—H8A109.7O2—C30—N8121.49 (14)
C3—C8—H8B109.7O2—C30—C20122.90 (14)
C7—C8—H8B109.7N8—C30—C20115.61 (13)
H8A—C8—H8B108.2N7—C31—C32116.67 (15)
C5—C9—C1109.88 (13)N7—C31—H31A121.7
C5—C9—H9A109.7C32—C31—H31A121.7
C1—C9—H9A109.7C33—C32—N6104.13 (14)
C5—C9—H9B109.7C33—C32—C31133.72 (16)
C1—C9—H9B109.7N6—C32—C31122.04 (15)
H9A—C9—H9B108.2C32—C33—N5111.78 (15)
C7—C10—C1110.06 (13)C32—C33—Cl2126.87 (13)
C7—C10—H10A109.6N5—C33—Cl2121.32 (12)
C1—C10—H10A109.6N5—C34—N6111.12 (15)
C7—C10—H10B109.6N5—C34—C35126.11 (15)
C1—C10—H10B109.6N6—C34—C35122.77 (15)
H10A—C10—H10B108.2C34—C35—C36113.43 (14)
O1—C11—N1121.44 (15)C34—C35—H35A108.9
O1—C11—C1122.50 (14)C36—C35—H35A108.9
N1—C11—C1116.03 (14)C34—C35—H35B108.9
N2—C12—C13116.98 (15)C36—C35—H35B108.9
N2—C12—H12A121.5H35A—C35—H35B107.7
C13—C12—H12A121.5C37—C36—C35114.70 (14)
C14—C13—N3103.96 (14)C37—C36—H36A108.6
C14—C13—C12133.60 (15)C35—C36—H36A108.6
N3—C13—C12122.43 (14)C37—C36—H36B108.6
N4—C14—C13111.82 (14)C35—C36—H36B108.6
N4—C14—Cl1121.52 (12)H36A—C36—H36B107.6
C13—C14—Cl1126.65 (13)C36—C37—C38111.99 (16)
N4—C15—N3111.47 (14)C36—C37—H37A109.2
N4—C15—C16123.95 (15)C38—C37—H37A109.2
N3—C15—C16124.58 (15)C36—C37—H37B109.2
C15—C16—C17113.03 (15)C38—C37—H37B109.2
C15—C16—H16A109.0H37A—C37—H37B107.9
C17—C16—H16A109.0C37—C38—H38A109.5
C15—C16—H16B109.0C37—C38—H38B109.5
C17—C16—H16B109.0H38A—C38—H38B109.5
H16A—C16—H16B107.8C37—C38—H38C109.5
C18—C17—C16113.12 (16)H38A—C38—H38C109.5
C18—C17—H17A109.0H38B—C38—H38C109.5
C16—C17—H17A109.0O3—C39—C40111.29 (15)
C18—C17—H17B109.0O3—C39—H39A109.4
C16—C17—H17B109.0C40—C39—H39A109.4
H17A—C17—H17B107.8O3—C39—H39B109.4
C17—C18—C19113.7 (2)C40—C39—H39B109.4
C17—C18—H18A108.8H39A—C39—H39B108.0
C19—C18—H18A108.8C39—C40—H40A109.5
C17—C18—H18B108.8C39—C40—H40B109.5
C19—C18—H18B108.8H40A—C40—H40B109.5
H18A—C18—H18B107.7C39—C40—H40C109.5
C18—C19—H19A109.5H40A—C40—H40C109.5
C18—C19—H19B109.5H40B—C40—H40C109.5
C11—N1—N2—C12172.14 (15)C16—C17—C18—C19179.65 (17)
C31—N7—N8—C30178.67 (14)C30—C20—C21—C22179.26 (13)
C11—C1—C2—C3179.27 (13)C25—C20—C21—C2259.15 (17)
C10—C1—C2—C358.29 (17)C29—C20—C21—C2258.94 (17)
C9—C1—C2—C360.33 (16)C20—C21—C22—C2360.07 (17)
C1—C2—C3—C859.13 (17)C20—C21—C22—C2860.09 (17)
C1—C2—C3—C461.03 (17)C28—C22—C23—C2459.73 (17)
C8—C3—C4—C559.27 (17)C21—C22—C23—C2460.19 (17)
C2—C3—C4—C560.79 (17)C22—C23—C24—C2660.06 (17)
C3—C4—C5—C960.18 (17)C22—C23—C24—C2560.10 (18)
C3—C4—C5—C659.74 (17)C30—C20—C25—C24177.94 (13)
C4—C5—C6—C760.22 (18)C21—C20—C25—C2458.94 (17)
C9—C5—C6—C759.97 (18)C29—C20—C25—C2459.30 (17)
C5—C6—C7—C1059.72 (18)C23—C24—C25—C2060.05 (18)
C5—C6—C7—C859.99 (18)C26—C24—C25—C2060.30 (18)
C4—C3—C8—C758.87 (18)C23—C24—C26—C2760.04 (17)
C2—C3—C8—C760.61 (18)C25—C24—C26—C2760.28 (18)
C6—C7—C8—C359.44 (17)C24—C26—C27—C2859.71 (17)
C10—C7—C8—C360.78 (17)C24—C26—C27—C2960.39 (17)
C4—C5—C9—C159.58 (17)C26—C27—C28—C2259.40 (17)
C6—C5—C9—C160.39 (17)C29—C27—C28—C2260.76 (17)
C11—C1—C9—C5178.64 (13)C23—C22—C28—C2759.40 (17)
C10—C1—C9—C559.78 (17)C21—C22—C28—C2760.66 (17)
C2—C1—C9—C559.34 (16)C26—C27—C29—C2060.15 (17)
C6—C7—C10—C159.86 (18)C28—C27—C29—C2060.16 (17)
C8—C7—C10—C160.24 (17)C30—C20—C29—C27178.60 (13)
C11—C1—C10—C7178.20 (13)C25—C20—C29—C2759.28 (17)
C9—C1—C10—C759.33 (17)C21—C20—C29—C2758.88 (17)
C2—C1—C10—C759.24 (17)N7—N8—C30—O20.1 (2)
N2—N1—C11—O17.1 (2)N7—N8—C30—C20179.67 (12)
N2—N1—C11—C1170.95 (13)C25—C20—C30—O217.2 (2)
C10—C1—C11—O15.6 (2)C21—C20—C30—O2138.20 (15)
C9—C1—C11—O1113.00 (17)C29—C20—C30—O2101.38 (17)
C2—C1—C11—O1126.86 (16)C25—C20—C30—N8163.04 (13)
C10—C1—C11—N1176.36 (14)C21—C20—C30—N842.05 (18)
C9—C1—C11—N165.00 (17)C29—C20—C30—N878.37 (16)
C2—C1—C11—N155.14 (18)N8—N7—C31—C32178.15 (13)
N1—N2—C12—C13176.98 (14)C34—N6—C32—C330.49 (17)
C15—N3—C13—C140.20 (18)C34—N6—C32—C31176.12 (14)
C15—N3—C13—C12179.78 (15)N7—C31—C32—C33173.00 (17)
N2—C12—C13—C14174.59 (17)N7—C31—C32—N62.4 (2)
N2—C12—C13—N36.0 (2)N6—C32—C33—N50.36 (18)
C15—N4—C14—C130.44 (19)C31—C32—C33—N5175.66 (16)
C15—N4—C14—Cl1178.68 (12)N6—C32—C33—Cl2178.57 (12)
N3—C13—C14—N40.40 (18)C31—C32—C33—Cl22.6 (3)
C12—C13—C14—N4179.91 (17)C34—N5—C33—C320.08 (18)
N3—C13—C14—Cl1178.66 (12)C34—N5—C33—Cl2178.41 (12)
C12—C13—C14—Cl10.8 (3)C33—N5—C34—N60.24 (17)
C14—N4—C15—N30.30 (19)C33—N5—C34—C35179.45 (15)
C14—N4—C15—C16178.97 (16)C32—N6—C34—N50.47 (18)
C13—N3—C15—N40.06 (19)C32—N6—C34—C35179.23 (15)
C13—N3—C15—C16179.20 (15)N5—C34—C35—C3663.0 (2)
N4—C15—C16—C1784.5 (2)N6—C34—C35—C36117.35 (17)
N3—C15—C16—C1794.6 (2)C34—C35—C36—C3756.7 (2)
C15—C16—C17—C1876.1 (2)C35—C36—C37—C38176.31 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.86 (1)2.00 (1)2.841 (2)166 (2)
N3—H3···O1wii0.86 (1)1.95 (1)2.806 (2)170 (2)
N6—H6···O2w0.88 (1)1.95 (1)2.829 (2)174 (2)
N8—H8···O3wiii0.86 (1)1.94 (1)2.778 (2)164 (2)
O3—H3o···O1w0.84 (1)1.84 (1)2.673 (2)177 (2)
O1w—H11···O1ii0.84 (1)2.00 (1)2.821 (2)166 (2)
O1w—H12···N50.84 (1)1.91 (1)2.751 (2)175 (3)
O2w—H21···O20.85 (1)2.07 (1)2.905 (2)172 (2)
O2w—H22···O2iv0.84 (1)1.93 (1)2.764 (2)176 (2)
O3w—H31···N40.84 (1)1.94 (1)2.773 (2)169 (2)
O3w—H32···O2w0.85 (1)1.92 (1)2.766 (2)174 (2)
Symmetry codes: (i) x+2, y+2, z+1; (ii) x+1, y+2, z+1; (iii) x+1, y, z; (iv) x+1, y+2, z.

Experimental details

Crystal data
Chemical formulaC19H27ClN4O·0.5C2H6O·1.5H2O
Mr412.95
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)7.9867 (6), 16.8478 (13), 16.9656 (13)
α, β, γ (°)97.341 (1), 100.376 (1), 97.505 (1)
V3)2199.3 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.40 × 0.10 × 0.10
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.924, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
21291, 10050, 7547
Rint0.036
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.113, 1.02
No. of reflections10050
No. of parameters552
No. of restraints11
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.37, 0.43

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.86 (1)2.00 (1)2.841 (2)166 (2)
N3—H3···O1wii0.86 (1)1.95 (1)2.806 (2)170 (2)
N6—H6···O2w0.88 (1)1.95 (1)2.829 (2)174 (2)
N8—H8···O3wiii0.86 (1)1.94 (1)2.778 (2)164 (2)
O3—H3o···O1w0.84 (1)1.84 (1)2.673 (2)177 (2)
O1w—H11···O1ii0.84 (1)2.00 (1)2.821 (2)166 (2)
O1w—H12···N50.84 (1)1.91 (1)2.751 (2)175 (3)
O2w—H21···O20.85 (1)2.07 (1)2.905 (2)172 (2)
O2w—H22···O2iv0.84 (1)1.93 (1)2.764 (2)176 (2)
O3w—H31···N40.84 (1)1.94 (1)2.773 (2)169 (2)
O3w—H32···O2w0.85 (1)1.92 (1)2.766 (2)174 (2)
Symmetry codes: (i) x+2, y+2, z+1; (ii) x+1, y+2, z+1; (iii) x+1, y, z; (iv) x+1, y+2, z.
 

Acknowledgements

We thank King Saud University and the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS
First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationKadi, A. A., El-Brollosy, N. R., Al-Deeb, O. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2007). Eur. J. Med. Chem. 42, 235–242.  Web of Science CrossRef PubMed CAS
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals

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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds