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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o2131.
Published online 2010 July 31. doi:  10.1107/S1600536810029260
PMCID: PMC3007568

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

Abstract

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 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2131-scheme1.jpg

Experimental

Crystal data

  • C19H27ClN4O·0.5C2H6O·1.5H2O
  • M r = 412.95
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2131-efi1.jpg
  • 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 [triangle]) T min = 0.924, T max = 0.980
  • 21291 measured reflections
  • 10050 independent reflections
  • 7547 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 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

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810029260/bt5304sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029260/bt5304Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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–N═CH– 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).

Experimental

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

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.

Figures

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.
Fig. 2.
Hydrogen-bonded layer structure.

Crystal data

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

Bruker SMART APEX diffractometer10050 independent reflections
Radiation source: fine-focus sealed tube7547 reflections with I > 2σ(I)
graphiteRint = 0.036
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.924, Tmax = 0.980k = −22→21
21291 measured reflectionsl = −21→21

Refinement

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 = 1.02w = 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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)
H240.99921.3218−0.00640.028*
C250.9281 (2)1.21643 (10)0.04083 (11)0.0201 (4)
H25A0.86451.24290.07900.024*
H25B0.84391.1900−0.00880.024*
C261.1560 (2)1.23945 (11)−0.04119 (11)0.0259 (4)
H26A1.07301.2130−0.09110.031*
H26B1.24021.2805−0.05620.031*
C271.2497 (2)1.17624 (10)−0.00257 (10)0.0206 (4)
H271.31251.1496−0.04190.025*
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*
H29B1.03551.0849−0.03060.022*
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)

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, °)

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—C12−172.14 (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—C22−59.15 (17)
C10—C1—C2—C358.29 (17)C29—C20—C21—C2258.94 (17)
C9—C1—C2—C3−60.33 (16)C20—C21—C22—C2360.07 (17)
C1—C2—C3—C8−59.13 (17)C20—C21—C22—C28−60.09 (17)
C1—C2—C3—C461.03 (17)C28—C22—C23—C2459.73 (17)
C8—C3—C4—C559.27 (17)C21—C22—C23—C24−60.19 (17)
C2—C3—C4—C5−60.79 (17)C22—C23—C24—C26−60.06 (17)
C3—C4—C5—C960.18 (17)C22—C23—C24—C2560.10 (18)
C3—C4—C5—C6−59.74 (17)C30—C20—C25—C24−177.94 (13)
C4—C5—C6—C760.22 (18)C21—C20—C25—C2458.94 (17)
C9—C5—C6—C7−59.97 (18)C29—C20—C25—C24−59.30 (17)
C5—C6—C7—C1059.72 (18)C23—C24—C25—C20−60.05 (18)
C5—C6—C7—C8−59.99 (18)C26—C24—C25—C2060.30 (18)
C4—C3—C8—C7−58.87 (18)C23—C24—C26—C2760.04 (17)
C2—C3—C8—C760.61 (18)C25—C24—C26—C27−60.28 (18)
C6—C7—C8—C359.44 (17)C24—C26—C27—C28−59.71 (17)
C10—C7—C8—C3−60.78 (17)C24—C26—C27—C2960.39 (17)
C4—C5—C9—C1−59.58 (17)C26—C27—C28—C2259.40 (17)
C6—C5—C9—C160.39 (17)C29—C27—C28—C22−60.76 (17)
C11—C1—C9—C5−178.64 (13)C23—C22—C28—C27−59.40 (17)
C10—C1—C9—C5−59.78 (17)C21—C22—C28—C2760.66 (17)
C2—C1—C9—C559.34 (16)C26—C27—C29—C20−60.15 (17)
C6—C7—C10—C1−59.86 (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—C27−58.88 (17)
C2—C1—C10—C7−59.24 (17)N7—N8—C30—O20.1 (2)
N2—N1—C11—O1−7.1 (2)N7—N8—C30—C20−179.67 (12)
N2—N1—C11—C1170.95 (13)C25—C20—C30—O217.2 (2)
C10—C1—C11—O1−5.6 (2)C21—C20—C30—O2138.20 (15)
C9—C1—C11—O1113.00 (17)C29—C20—C30—O2−101.38 (17)
C2—C1—C11—O1−126.86 (16)C25—C20—C30—N8−163.04 (13)
C10—C1—C11—N1176.36 (14)C21—C20—C30—N8−42.05 (18)
C9—C1—C11—N1−65.00 (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—C14−0.20 (18)C34—N6—C32—C31−176.12 (14)
C15—N3—C13—C12−179.78 (15)N7—C31—C32—C33−173.00 (17)
N2—C12—C13—C14174.59 (17)N7—C31—C32—N62.4 (2)
N2—C12—C13—N3−6.0 (2)N6—C32—C33—N5−0.36 (18)
C15—N4—C14—C13−0.44 (19)C31—C32—C33—N5175.66 (16)
C15—N4—C14—Cl1178.68 (12)N6—C32—C33—Cl2−178.57 (12)
N3—C13—C14—N40.40 (18)C31—C32—C33—Cl2−2.6 (3)
C12—C13—C14—N4179.91 (17)C34—N5—C33—C320.08 (18)
N3—C13—C14—Cl1−178.66 (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—C35−179.45 (15)
C14—N4—C15—C16−178.97 (16)C32—N6—C34—N5−0.47 (18)
C13—N3—C15—N4−0.06 (19)C32—N6—C34—C35179.23 (15)
C13—N3—C15—C16179.20 (15)N5—C34—C35—C36−63.0 (2)
N4—C15—C16—C1784.5 (2)N6—C34—C35—C36117.35 (17)
N3—C15—C16—C17−94.6 (2)C34—C35—C36—C37−56.7 (2)
C15—C16—C17—C1876.1 (2)C35—C36—C37—C38−176.31 (15)

Hydrogen-bond geometry (Å, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5304).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • 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. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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