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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1196–o1197.
Published online 2009 May 7. doi:  10.1107/S1600536809015906
PMCID: PMC2969596

N′-[(E)-4-Chloro­benzyl­idene]-2-(4-isobutyl­phen­yl)propanohydrazide

Abstract

The asymmetric unit of title compound, C20H23ClN2O, consists of two crystallographically independent mol­ecules (A and B) in which the orientations of the 4-isobutyl­phenyl units are different. The isobutyl group of mol­ecule B is disordered over two positions with occupancies of 0.850 (5) and 0.150 (5). The dihedral angle between the two benzene rings is 88.70 (9)° in mol­ecule A and 89.38 (9)° in mol­ecule B. The independent mol­ecules are linked together into chains along [100] by N—H(...)O and C—H(...)O hydrogen bonds, and by C—H(...)π inter­actions. In the chain, N—H(...)O and C—H(...)O hydrogen bonds generate R 2 1(6) ring motifs. In addition, C—H(...)N hydrogen bonds are observed. The presence of pseudosymmetry in the structure suggests the higher symmetry space group Pbca but attempts to refine the structure in this space group resulted in high R (0.119) and wR (0.296) values.

Related literature

For general background and biological applications of hydrazone compounds, see: Kawail et al. (2005 [triangle]); Klasser & Epstein, (2005 [triangle]); Sridhar & Perumal (2003 [triangle]); Bedia et al. (2006 [triangle]); Rollas et al. (2002 [triangle]); Terzioglu & Gürsoy, (2003 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For the crystal structure of the bromo analogue, see: Fun et al. (2009 [triangle]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1196-scheme1.jpg

Experimental

Crystal data

  • C20H23ClN2O
  • M r = 342.85
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1196-efi1.jpg
  • a = 9.1405 (1) Å
  • b = 11.9260 (2) Å
  • c = 33.3487 (5) Å
  • V = 3635.33 (9) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.22 mm−1
  • T = 100 K
  • 0.56 × 0.18 × 0.15 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.887, T max = 0.967
  • 26510 measured reflections
  • 10652 independent reflections
  • 8888 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.118
  • S = 1.02
  • 10652 reflections
  • 453 parameters
  • H-atom parameters constrained
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.26 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 4712 Friedel pairs
  • Flack parameter: 0.10 (5)

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Selected torsion angles (°)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015906/ci2793sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015906/ci2793Isup2.hkl

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

Acknowledgments

HKF thanks Universiti Sains Malaysia for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). CSY thanks the Malaysian Government and Universiti Sains Malaysia for the award of a post of research officer under the Science Fund (grant No. 305/PFIZIK/613312).

supplementary crystallographic information

Comment

Non-steroidal anti-inflammatory drugs (NSAIDs) such as ibuprofen are widely used in the treatment of pain and inflammation (Kawail et al., 2005; Klasser & Epstein, 2005). Aryl hydrazones are important building blocks for the synthesis of a variety of heterocyclic compounds such as pyrazolines and pyrazoles (Sridhar & Perumal, 2003). Aryl hydrazones have been most conveniently synthesized by the reaction of aryl hydrazines with carbonyl compounds. Hydrazones possessing an azometine -NHN=CH- proton constitute an important class of compounds for new drug development. Hydrazones have been demonstrated to possess antimicrobial, anticonvulsant, analgesic, antiinflammatory, antiplatelet, antitubercular, anticancer and antitumoral activities (Bedia et al., 2006; Rollas et al., 2002; Terzioglu & Gürsoy, 2003). These observations have been the guide for the development of new hydrazones that possess varied biological activities. Prompted by these observations, the title compoud was synthesized and its crystal structure is reported here.

The asymmetric unit of title compound (Fig. 1), consists of two crystallographically independent molecules, A and B, in which the orientations of the 4-isobutylphenyl units are different (Table 1). Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable with those in the bromo analogue (Fun et al., 2009). The dihedral angle between the two benzene rings is 88.70 (9)° in molecule A and 89.38 (9)° in molecule B. The molecule A is linked to the molecule B by intermolecular C7A—H7AA···O1B and N2A—H1NA···O1B hydrogen bonds, generating an R21(6) ring motif (Bernstein et al., 1995) and by an C—H···π interaction.

In the crystal structure, the independent molecules are linked together into chains along the [100] (Fig. 2) by N—H···O and C—H···O hydrogen bonds, and C—H···π interactions (Table 2). In addition, C—H···N hydrogen bonds are observed.

Experimental

A mixture of 2-[4-(2-methylpropyl)phenyl]propanehydrazide (0.01 mol) and 4-chlorobenzaldehyde (0.01 mol) in ethanol (30 ml) along with 3 drops of concentrated sulphuric acid was refluxed for 1 h. Excess ethanol was removed from the reaction mixture under reduced pressure. The solid product obtained was filtered, washed with ethanol and dried. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution (yield 87%; m.p.430-433 K).

Refinement

The isopropyl group of molecule B is disordered over two positions with occupancies of 0.850 (5) and 0.150 (5). H atoms were positioned geometrically and refined using a riding model, with N-H = 0.86 Å, C-H = 0.93–0.98 Å and Uiso(H) = 1.2-1.5 Ueq(N, C). A rotating-group model was applied for the methyl groups. The presence of pseudo-symmetry in the structure suggests a higher symmetry space group Pbca. But attempts to refine the structure in the space group Pbca resulted in a more disordered model with high R (0.119) and wR (0.296) values.

Figures

Fig. 1.
The asymmetric unit of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms. Hydrogen bonds are shown as dashed lines. Both disorder components are shown.
Fig. 2.
The crystal packing of of the title compound, viewed down the b axis, showing chains along the [100]. Hydrogen bonds are shown as dashed lines. Only the major disorder component is shown.

Crystal data

C20H23ClN2OF(000) = 1456
Mr = 342.85Dx = 1.253 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 7618 reflections
a = 9.1405 (1) Åθ = 2.4–30.0°
b = 11.9260 (2) ŵ = 0.22 mm1
c = 33.3487 (5) ÅT = 100 K
V = 3635.33 (9) Å3Block, colourless
Z = 80.56 × 0.18 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer10652 independent reflections
Radiation source: fine-focus sealed tube8888 reflections with I > 2σ(I)
graphiteRint = 0.033
[var phi] and ω scansθmax = 30.1°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −12→12
Tmin = 0.887, Tmax = 0.967k = −13→16
26510 measured reflectionsl = −46→46

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.118w = 1/[σ2(Fo2) + (0.0575P)2 + 0.6608P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
10652 reflectionsΔρmax = 0.28 e Å3
453 parametersΔρmin = −0.25 e Å3
0 restraintsAbsolute structure: Flack (1983), 4712 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.10 (5)

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)

xyzUiso*/UeqOcc. (<1)
Cl1A0.85958 (7)−0.01289 (4)0.079925 (15)0.03026 (12)
O1A0.87919 (14)0.49658 (12)0.27831 (4)0.0223 (3)
N1A0.72753 (18)0.36296 (13)0.22621 (5)0.0175 (3)
N2A0.66284 (18)0.44256 (13)0.25054 (4)0.0172 (3)
H1NA0.56990.45340.24930.021*
C1A0.8193 (2)0.16989 (16)0.17979 (5)0.0191 (4)
H1AA0.86880.17890.20390.023*
C2A0.8699 (2)0.09272 (16)0.15182 (6)0.0215 (4)
H2AA0.95260.04970.15710.026*
C3A0.7946 (2)0.08102 (16)0.11585 (6)0.0215 (4)
C4A0.6700 (2)0.14204 (16)0.10760 (6)0.0227 (4)
H4AA0.62060.13240.08350.027*
C5A0.6195 (2)0.21807 (16)0.13586 (6)0.0207 (4)
H5AA0.53460.25870.13070.025*
C6A0.6943 (2)0.23433 (16)0.17187 (5)0.0181 (4)
C7A0.6421 (2)0.32052 (15)0.19980 (5)0.0184 (4)
H7AA0.54560.34470.19830.022*
C8A0.7450 (2)0.50325 (15)0.27615 (5)0.0164 (4)
C9A0.6584 (2)0.58104 (15)0.30371 (5)0.0161 (3)
H9AA0.56180.59330.29170.019*
C10A0.6374 (2)0.51916 (15)0.34336 (5)0.0173 (3)
C11A0.5317 (2)0.43554 (16)0.34657 (6)0.0186 (4)
H11A0.47300.41880.32460.022*
C12A0.5130 (2)0.37699 (16)0.38200 (6)0.0207 (4)
H12A0.44110.32190.38340.025*
C13A0.5986 (2)0.39827 (16)0.41551 (5)0.0204 (4)
C14A0.7039 (2)0.48227 (17)0.41241 (6)0.0233 (4)
H14A0.76240.49870.43450.028*
C15A0.7232 (2)0.54207 (16)0.37695 (5)0.0212 (4)
H15A0.79410.59790.37560.025*
C16A0.5822 (2)0.32870 (16)0.45308 (6)0.0247 (4)
H16A0.47920.32260.45970.030*
H16B0.63050.36680.47510.030*
C17A0.6470 (2)0.21025 (16)0.44874 (6)0.0235 (4)
H17A0.59960.17380.42580.028*
C18A0.8110 (2)0.21425 (19)0.44058 (7)0.0314 (5)
H18A0.84700.13950.43640.047*
H18B0.86020.24720.46310.047*
H18C0.82920.25860.41710.047*
C19A0.6155 (3)0.14012 (19)0.48615 (6)0.0357 (5)
H19A0.65710.06680.48300.053*
H19B0.51160.13370.48980.053*
H19C0.65790.17590.50920.053*
C20A0.7355 (2)0.69465 (16)0.30705 (6)0.0203 (4)
H20A0.68580.74030.32650.030*
H20B0.73380.73150.28150.030*
H20C0.83500.68340.31530.030*
Cl1B0.35621 (6)−0.01924 (4)0.418134 (16)0.03065 (12)
O1B0.38166 (14)0.50246 (12)0.22302 (4)0.0224 (3)
N1B0.23212 (17)0.37147 (13)0.27639 (5)0.0183 (3)
N2B0.16586 (18)0.44848 (14)0.25107 (4)0.0189 (3)
H1NB0.07290.45900.25230.023*
C1B0.3149 (2)0.17172 (17)0.32054 (6)0.0210 (4)
H1BA0.36050.17920.29580.025*
C2B0.3619 (2)0.09038 (16)0.34692 (6)0.0214 (4)
H2BA0.43720.04190.33980.026*
C3B0.2958 (2)0.08155 (16)0.38423 (6)0.0217 (4)
C4B0.1802 (2)0.15040 (17)0.39501 (6)0.0235 (4)
H4BA0.13610.14330.42000.028*
C5B0.1313 (2)0.22994 (16)0.36785 (6)0.0207 (4)
H5BA0.05220.27530.37450.025*
C6B0.1994 (2)0.24292 (15)0.33062 (5)0.0178 (4)
C7B0.1467 (2)0.33044 (16)0.30332 (5)0.0192 (4)
H7BA0.05110.35640.30550.023*
C8B0.2472 (2)0.50689 (16)0.22453 (5)0.0177 (4)
C9B0.1567 (2)0.57335 (16)0.19427 (5)0.0184 (4)
H9BA0.05960.58750.20570.022*
C10B0.1401 (2)0.49807 (15)0.15762 (5)0.0166 (3)
C11B0.0116 (2)0.43596 (16)0.15239 (6)0.0204 (4)
H11B−0.06520.44420.17040.025*
C12B−0.0020 (2)0.36179 (16)0.12028 (6)0.0201 (4)
H12B−0.08890.32230.11700.024*
C13B0.1114 (2)0.34555 (15)0.09307 (5)0.0189 (4)
C14B0.2380 (2)0.40909 (17)0.09833 (6)0.0221 (4)
H14B0.31500.40090.08030.027*
C15B0.2516 (2)0.48440 (17)0.12987 (5)0.0221 (4)
H15B0.33690.52630.13240.026*
C16B0.0976 (2)0.26297 (16)0.05913 (5)0.0225 (4)
H16C0.06080.19380.06980.027*0.850 (5)
H16D0.19350.24850.04860.027*0.850 (5)
H16E0.01560.21520.06470.027*0.150 (5)
H16F0.18350.21670.05930.027*0.150 (5)
C17B−0.0010 (3)0.2988 (2)0.02462 (7)0.0242 (6)0.850 (5)
H17B−0.10120.30440.03480.029*0.850 (5)
C18B0.0013 (3)0.2096 (3)−0.00823 (9)0.0302 (7)0.850 (5)
H18D−0.06310.2315−0.02960.045*0.850 (5)
H18E−0.03070.13920.00270.045*0.850 (5)
H18F0.09900.2018−0.01840.045*0.850 (5)
C19B0.0411 (5)0.4117 (2)0.00756 (8)0.0498 (10)0.850 (5)
H19D0.03120.46810.02790.075*0.850 (5)
H19E−0.02190.4295−0.01460.075*0.850 (5)
H19F0.14070.4093−0.00150.075*0.850 (5)
C17C0.0720 (16)0.3086 (10)0.0176 (4)0.014 (2)*0.150 (5)
H17C0.16010.34970.00950.017*0.150 (5)
C18C0.0557 (15)0.2076 (14)−0.0106 (5)0.014 (2)*0.15
H18G0.13790.1583−0.00730.021*0.150 (5)
H18H0.05180.2332−0.03790.021*0.150 (5)
H18I−0.03280.1680−0.00430.021*0.150 (5)
C19C−0.0562 (16)0.3885 (12)0.0151 (4)0.023 (3)*0.150 (5)
H19G−0.03600.45390.03090.035*0.150 (5)
H19H−0.14250.35220.02510.035*0.150 (5)
H19I−0.07140.4101−0.01230.035*0.150 (5)
C20B0.2306 (2)0.68628 (17)0.18538 (6)0.0234 (4)
H20D0.22720.73270.20890.035*
H20E0.18020.72300.16380.035*
H20F0.33070.67380.17790.035*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl1A0.0455 (3)0.0200 (2)0.0253 (2)−0.0009 (2)0.0077 (2)−0.0070 (2)
O1A0.0167 (6)0.0280 (7)0.0221 (7)0.0015 (6)−0.0005 (5)−0.0034 (6)
N1A0.0202 (7)0.0167 (7)0.0157 (7)0.0004 (6)0.0024 (6)−0.0009 (6)
N2A0.0159 (8)0.0183 (8)0.0173 (7)0.0035 (6)−0.0023 (6)−0.0022 (6)
C1A0.0247 (10)0.0162 (9)0.0163 (9)−0.0019 (8)−0.0005 (8)0.0012 (7)
C2A0.0259 (10)0.0167 (9)0.0219 (9)0.0005 (8)0.0050 (8)0.0019 (7)
C3A0.0316 (10)0.0146 (9)0.0183 (9)−0.0041 (8)0.0048 (8)−0.0033 (8)
C4A0.0300 (10)0.0201 (10)0.0179 (9)−0.0050 (8)−0.0008 (8)−0.0021 (8)
C5A0.0222 (10)0.0190 (9)0.0211 (9)−0.0042 (8)−0.0002 (8)0.0009 (7)
C6A0.0209 (10)0.0168 (9)0.0167 (8)−0.0033 (7)0.0015 (7)0.0017 (7)
C7A0.0190 (8)0.0182 (9)0.0181 (8)−0.0018 (8)0.0001 (7)0.0011 (7)
C8A0.0188 (9)0.0162 (9)0.0143 (8)0.0017 (7)−0.0011 (7)0.0016 (7)
C9A0.0171 (8)0.0167 (8)0.0146 (8)0.0022 (7)−0.0001 (7)0.0007 (7)
C10A0.0193 (8)0.0153 (8)0.0171 (8)0.0028 (7)−0.0001 (7)−0.0008 (7)
C11A0.0188 (9)0.0174 (9)0.0197 (9)0.0013 (7)−0.0020 (7)−0.0021 (7)
C12A0.0201 (9)0.0160 (9)0.0259 (10)−0.0024 (7)0.0032 (8)−0.0016 (8)
C13A0.0272 (9)0.0166 (9)0.0175 (8)0.0009 (7)0.0051 (7)0.0006 (7)
C14A0.0286 (10)0.0252 (10)0.0161 (8)−0.0054 (8)−0.0029 (7)−0.0001 (7)
C15A0.0235 (9)0.0208 (9)0.0193 (9)−0.0073 (8)−0.0002 (7)−0.0004 (7)
C16A0.0336 (10)0.0217 (9)0.0189 (9)0.0003 (8)0.0056 (8)0.0010 (8)
C17A0.0304 (10)0.0198 (9)0.0203 (9)0.0000 (8)0.0009 (8)0.0018 (7)
C18A0.0295 (11)0.0303 (11)0.0344 (11)0.0014 (9)−0.0031 (9)0.0033 (9)
C19A0.0532 (14)0.0260 (11)0.0278 (11)0.0021 (10)0.0060 (10)0.0099 (9)
C20A0.0242 (9)0.0162 (9)0.0205 (9)0.0001 (7)0.0007 (7)0.0021 (7)
Cl1B0.0338 (3)0.0233 (2)0.0348 (3)0.0022 (2)−0.0057 (2)0.0096 (2)
O1B0.0165 (6)0.0305 (8)0.0202 (6)0.0027 (6)−0.0005 (5)0.0010 (6)
N1B0.0198 (8)0.0185 (8)0.0164 (7)0.0032 (6)−0.0025 (6)−0.0019 (6)
N2B0.0157 (8)0.0225 (9)0.0186 (8)0.0040 (7)−0.0030 (6)0.0008 (6)
C1B0.0202 (9)0.0222 (10)0.0207 (9)0.0012 (8)−0.0011 (8)−0.0035 (8)
C2B0.0200 (9)0.0164 (9)0.0279 (10)0.0009 (8)−0.0007 (8)−0.0032 (8)
C3B0.0226 (9)0.0162 (9)0.0262 (10)−0.0016 (8)−0.0058 (8)0.0020 (8)
C4B0.0255 (10)0.0238 (10)0.0213 (9)−0.0026 (8)0.0000 (8)0.0005 (8)
C5B0.0188 (9)0.0187 (9)0.0245 (9)0.0019 (8)0.0019 (8)−0.0006 (7)
C6B0.0173 (9)0.0167 (9)0.0194 (9)0.0003 (7)−0.0032 (7)0.0000 (7)
C7B0.0176 (8)0.0195 (9)0.0206 (9)0.0036 (8)−0.0024 (8)−0.0019 (7)
C8B0.0193 (9)0.0188 (9)0.0150 (8)0.0004 (8)−0.0013 (7)−0.0045 (7)
C9B0.0169 (8)0.0196 (9)0.0187 (8)0.0016 (8)−0.0021 (7)−0.0001 (7)
C10B0.0189 (8)0.0173 (9)0.0138 (7)0.0013 (7)−0.0022 (7)0.0021 (7)
C11B0.0182 (9)0.0234 (10)0.0196 (9)−0.0026 (8)−0.0001 (7)0.0011 (8)
C12B0.0208 (9)0.0185 (9)0.0210 (9)−0.0063 (7)−0.0015 (7)0.0018 (7)
C13B0.0232 (9)0.0166 (8)0.0171 (8)0.0013 (7)−0.0040 (7)0.0012 (7)
C14B0.0202 (8)0.0282 (10)0.0181 (9)0.0001 (8)0.0010 (7)−0.0026 (8)
C15B0.0177 (8)0.0285 (10)0.0201 (9)−0.0043 (8)−0.0012 (7)−0.0011 (8)
C16B0.0272 (9)0.0192 (9)0.0211 (9)0.0010 (8)−0.0054 (7)−0.0023 (7)
C17B0.0253 (14)0.0268 (13)0.0203 (11)0.0026 (10)−0.0055 (10)−0.0049 (9)
C18B0.0330 (15)0.0326 (15)0.0251 (13)−0.0039 (14)−0.0069 (13)−0.0105 (11)
C19B0.101 (3)0.0250 (14)0.0231 (13)0.0006 (17)−0.0188 (17)−0.0003 (11)
C20B0.0252 (10)0.0195 (9)0.0255 (10)−0.0006 (8)−0.0045 (8)−0.0016 (8)

Geometric parameters (Å, °)

Cl1A—C3A1.744 (2)C1B—C2B1.378 (3)
O1A—C8A1.231 (2)C1B—C6B1.395 (3)
N1A—C7A1.281 (2)C1B—H1BA0.93
N1A—N2A1.382 (2)C2B—C3B1.387 (3)
N2A—C8A1.348 (2)C2B—H2BA0.93
N2A—H1NA0.86C3B—C4B1.386 (3)
C1A—C2A1.390 (3)C4B—C5B1.386 (3)
C1A—C6A1.402 (3)C4B—H4BA0.93
C1A—H1AA0.93C5B—C6B1.397 (3)
C2A—C3A1.390 (3)C5B—H5BA0.93
C2A—H2AA0.93C6B—C7B1.467 (3)
C3A—C4A1.379 (3)C7B—H7BA0.93
C4A—C5A1.387 (3)C8B—C9B1.527 (3)
C4A—H4AA0.93C9B—C10B1.524 (2)
C5A—C6A1.396 (3)C9B—C20B1.536 (3)
C5A—H5AA0.93C9B—H9BA0.98
C6A—C7A1.467 (3)C10B—C15B1.386 (3)
C7A—H7AA0.93C10B—C11B1.400 (3)
C8A—C9A1.527 (2)C11B—C12B1.394 (3)
C9A—C10A1.526 (2)C11B—H11B0.93
C9A—C20A1.531 (3)C12B—C13B1.392 (3)
C9A—H9AA0.98C12B—H12B0.93
C10A—C11A1.393 (3)C13B—C14B1.394 (3)
C10A—C15A1.394 (2)C13B—C16B1.506 (2)
C11A—C12A1.383 (3)C14B—C15B1.389 (3)
C11A—H11A0.93C14B—H14B0.93
C12A—C13A1.387 (3)C15B—H15B0.93
C12A—H12A0.93C16B—C17C1.507 (12)
C13A—C14A1.393 (3)C16B—C17B1.523 (3)
C13A—C16A1.510 (2)C16B—H16C0.96
C14A—C15A1.392 (3)C16B—H16D0.96
C14A—H14A0.93C16B—H16E0.96
C15A—H15A0.93C16B—H16F0.96
C16A—C17A1.539 (3)C17B—C19B1.511 (4)
C16A—H16A0.97C17B—C18B1.528 (3)
C16A—H16B0.97C17B—H17B0.98
C17A—C18A1.524 (3)C18B—H18D0.96
C17A—C19A1.529 (3)C18B—H18E0.96
C17A—H17A0.98C18B—H18F0.96
C18A—H18A0.96C19B—H19D0.96
C18A—H18B0.96C19B—H19E0.96
C18A—H18C0.96C19B—H19F0.96
C19A—H19A0.96C17C—C19C1.513 (19)
C19A—H19B0.96C17C—C18C1.535 (19)
C19A—H19C0.96C17C—H17C0.98
C20A—H20A0.96C18C—H18G0.96
C20A—H20B0.96C18C—H18H0.96
C20A—H20C0.96C18C—H18I0.96
Cl1B—C3B1.740 (2)C19C—H19G0.96
O1B—C8B1.231 (2)C19C—H19H0.96
N1B—C7B1.287 (2)C19C—H19I0.96
N1B—N2B1.387 (2)C20B—H20D0.96
N2B—C8B1.350 (2)C20B—H20E0.96
N2B—H1NB0.86C20B—H20F0.96
C7A—N1A—N2A114.48 (16)C1B—C2B—H2BA120.3
C8A—N2A—N1A120.17 (15)C3B—C2B—H2BA120.3
C8A—N2A—H1NA119.9C4B—C3B—C2B121.32 (18)
N1A—N2A—H1NA119.9C4B—C3B—Cl1B118.85 (16)
C2A—C1A—C6A120.52 (18)C2B—C3B—Cl1B119.82 (15)
C2A—C1A—H1AA119.7C5B—C4B—C3B118.79 (18)
C6A—C1A—H1AA119.7C5B—C4B—H4BA120.6
C1A—C2A—C3A118.74 (19)C3B—C4B—H4BA120.6
C1A—C2A—H2AA120.6C4B—C5B—C6B120.88 (18)
C3A—C2A—H2AA120.6C4B—C5B—H5BA119.6
C4A—C3A—C2A121.88 (18)C6B—C5B—H5BA119.6
C4A—C3A—Cl1A118.90 (15)C1B—C6B—C5B118.92 (17)
C2A—C3A—Cl1A119.22 (16)C1B—C6B—C7B122.13 (17)
C3A—C4A—C5A118.98 (18)C5B—C6B—C7B118.95 (17)
C3A—C4A—H4AA120.5N1B—C7B—C6B120.31 (18)
C5A—C4A—H4AA120.5N1B—C7B—H7BA119.8
C4A—C5A—C6A120.82 (19)C6B—C7B—H7BA119.8
C4A—C5A—H5AA119.6O1B—C8B—N2B123.68 (18)
C6A—C5A—H5AA119.6O1B—C8B—C9B122.43 (17)
C5A—C6A—C1A119.03 (18)N2B—C8B—C9B113.76 (16)
C5A—C6A—C7A118.98 (18)C10B—C9B—C8B106.14 (15)
C1A—C6A—C7A121.98 (17)C10B—C9B—C20B113.93 (15)
N1A—C7A—C6A121.01 (18)C8B—C9B—C20B110.15 (15)
N1A—C7A—H7AA119.5C10B—C9B—H9BA108.8
C6A—C7A—H7AA119.5C8B—C9B—H9BA108.8
O1A—C8A—N2A123.87 (17)C20B—C9B—H9BA108.8
O1A—C8A—C9A121.34 (17)C15B—C10B—C11B118.13 (17)
N2A—C8A—C9A114.77 (15)C15B—C10B—C9B122.11 (17)
C10A—C9A—C8A107.03 (14)C11B—C10B—C9B119.69 (17)
C10A—C9A—C20A115.01 (15)C12B—C11B—C10B120.44 (18)
C8A—C9A—C20A110.07 (15)C12B—C11B—H11B119.8
C10A—C9A—H9AA108.2C10B—C11B—H11B119.8
C8A—C9A—H9AA108.2C13B—C12B—C11B121.48 (18)
C20A—C9A—H9AA108.2C13B—C12B—H12B119.3
C11A—C10A—C15A117.96 (17)C11B—C12B—H12B119.3
C11A—C10A—C9A119.99 (16)C12B—C13B—C14B117.44 (17)
C15A—C10A—C9A122.04 (17)C12B—C13B—C16B121.24 (17)
C12A—C11A—C10A120.86 (18)C14B—C13B—C16B121.32 (17)
C12A—C11A—H11A119.6C15B—C14B—C13B121.42 (17)
C10A—C11A—H11A119.6C15B—C14B—H14B119.3
C11A—C12A—C13A121.73 (18)C13B—C14B—H14B119.3
C11A—C12A—H12A119.1C10B—C15B—C14B121.04 (17)
C13A—C12A—H12A119.1C10B—C15B—H15B119.5
C12A—C13A—C14A117.48 (17)C14B—C15B—H15B119.5
C12A—C13A—C16A120.79 (17)C13B—C16B—C17C117.9 (5)
C14A—C13A—C16A121.67 (17)C13B—C16B—C17B115.73 (16)
C15A—C14A—C13A121.26 (17)C13B—C16B—H16C108.2
C15A—C14A—H14A119.4C17C—C16B—H16C126.7
C13A—C14A—H14A119.4C17B—C16B—H16C108.4
C14A—C15A—C10A120.71 (17)C13B—C16B—H16D108.4
C14A—C15A—H15A119.6C17B—C16B—H16D108.3
C10A—C15A—H15A119.6H16C—C16B—H16D107.5
C13A—C16A—C17A112.86 (15)C13B—C16B—H16E107.9
C13A—C16A—H16A109.0C17C—C16B—H16E105.8
C17A—C16A—H16A109.0H16D—C16B—H16E132.7
C13A—C16A—H16B109.0C13B—C16B—H16F107.7
C17A—C16A—H16B109.0C17C—C16B—H16F109.8
H16A—C16A—H16B107.8C17B—C16B—H16F130.5
C18A—C17A—C19A110.38 (18)H16E—C16B—H16F107.3
C18A—C17A—C16A111.51 (17)C19B—C17B—C16B112.6 (2)
C19A—C17A—C16A110.67 (16)C19B—C17B—C18B110.3 (2)
C18A—C17A—H17A108.1C16B—C17B—C18B109.8 (2)
C19A—C17A—H17A108.1C19B—C17B—H17B108.0
C16A—C17A—H17A108.1C16B—C17B—H17B108.0
C17A—C18A—H18A109.5C18B—C17B—H17B108.0
C17A—C18A—H18B109.5C16B—C17C—C19C113.4 (10)
H18A—C18A—H18B109.5C16B—C17C—C18C107.2 (10)
C17A—C18A—H18C109.5C19C—C17C—C18C112.7 (11)
H18A—C18A—H18C109.5C16B—C17C—H17C107.8
H18B—C18A—H18C109.5C19C—C17C—H17C107.8
C17A—C19A—H19A109.5C18C—C17C—H17C107.8
C17A—C19A—H19B109.5C17C—C18C—H18G109.5
H19A—C19A—H19B109.5C17C—C18C—H18H109.5
C17A—C19A—H19C109.5H18G—C18C—H18H109.5
H19A—C19A—H19C109.5C17C—C18C—H18I109.5
H19B—C19A—H19C109.5H18G—C18C—H18I109.5
C9A—C20A—H20A109.5H18H—C18C—H18I109.5
C9A—C20A—H20B109.5C17C—C19C—H19G109.5
H20A—C20A—H20B109.5C17C—C19C—H19H109.5
C9A—C20A—H20C109.5H19G—C19C—H19H109.5
H20A—C20A—H20C109.5C17C—C19C—H19I109.5
H20B—C20A—H20C109.5H19G—C19C—H19I109.5
C7B—N1B—N2B114.31 (16)H19H—C19C—H19I109.5
C8B—N2B—N1B120.03 (16)C9B—C20B—H20D109.5
C8B—N2B—H1NB120.0C9B—C20B—H20E109.5
N1B—N2B—H1NB120.0H20D—C20B—H20E109.5
C2B—C1B—C6B120.68 (18)C9B—C20B—H20F109.5
C2B—C1B—H1BA119.7H20D—C20B—H20F109.5
C6B—C1B—H1BA119.7H20E—C20B—H20F109.5
C1B—C2B—C3B119.36 (18)
C7A—N1A—N2A—C8A−171.84 (16)C2B—C3B—C4B—C5B−0.6 (3)
C6A—C1A—C2A—C3A0.2 (3)Cl1B—C3B—C4B—C5B−179.42 (16)
C1A—C2A—C3A—C4A−1.3 (3)C3B—C4B—C5B—C6B−1.7 (3)
C1A—C2A—C3A—Cl1A178.34 (15)C2B—C1B—C6B—C5B−0.5 (3)
C2A—C3A—C4A—C5A0.7 (3)C2B—C1B—C6B—C7B179.92 (18)
Cl1A—C3A—C4A—C5A−178.97 (15)C4B—C5B—C6B—C1B2.2 (3)
C3A—C4A—C5A—C6A1.0 (3)C4B—C5B—C6B—C7B−178.22 (18)
C4A—C5A—C6A—C1A−2.1 (3)N2B—N1B—C7B—C6B176.26 (16)
C4A—C5A—C6A—C7A176.25 (17)C1B—C6B—C7B—N1B−24.7 (3)
C2A—C1A—C6A—C5A1.4 (3)C5B—C6B—C7B—N1B155.66 (18)
C2A—C1A—C6A—C7A−176.85 (18)N1B—N2B—C8B—O1B−5.5 (3)
N2A—N1A—C7A—C6A−179.59 (16)N1B—N2B—C8B—C9B170.38 (15)
C5A—C6A—C7A—N1A−158.07 (18)O1B—C8B—C9B—C10B82.4 (2)
C1A—C6A—C7A—N1A20.2 (3)N2B—C8B—C9B—C10B−93.60 (18)
N1A—N2A—C8A—O1A3.6 (3)O1B—C8B—C9B—C20B−41.4 (2)
N1A—N2A—C8A—C9A−175.07 (15)N2B—C8B—C9B—C20B142.63 (17)
O1A—C8A—C9A—C10A−82.3 (2)C8B—C9B—C10B—C15B−78.2 (2)
N2A—C8A—C9A—C10A96.38 (18)C20B—C9B—C10B—C11B−140.01 (18)
O1A—C8A—C9A—C20A43.3 (2)C20B—C9B—C10B—C15B43.2 (2)
N2A—C8A—C9A—C20A−137.99 (16)C8B—C9B—C10B—C11B98.61 (19)
C8A—C9A—C10A—C11A−77.7 (2)C15B—C10B—C11B—C12B0.7 (3)
C20A—C9A—C10A—C11A159.65 (17)C9B—C10B—C11B—C12B−176.29 (17)
C8A—C9A—C10A—C15A101.1 (2)C10B—C11B—C12B—C13B1.2 (3)
C20A—C9A—C10A—C15A−21.5 (3)C11B—C12B—C13B—C14B−2.1 (3)
C15A—C10A—C11A—C12A−0.2 (3)C11B—C12B—C13B—C16B178.27 (17)
C9A—C10A—C11A—C12A178.72 (17)C12B—C13B—C14B—C15B1.1 (3)
C10A—C11A—C12A—C13A−0.5 (3)C16B—C13B—C14B—C15B−179.27 (18)
C11A—C12A—C13A—C14A0.8 (3)C11B—C10B—C15B—C14B−1.7 (3)
C11A—C12A—C13A—C16A−176.36 (18)C9B—C10B—C15B—C14B175.23 (17)
C12A—C13A—C14A—C15A−0.5 (3)C13B—C14B—C15B—C10B0.8 (3)
C16A—C13A—C14A—C15A176.63 (18)C12B—C13B—C16B—C17C104.7 (7)
C13A—C14A—C15A—C10A−0.1 (3)C14B—C13B—C16B—C17C−75.0 (7)
C11A—C10A—C15A—C14A0.5 (3)C12B—C13B—C16B—C17B74.0 (3)
C9A—C10A—C15A—C14A−178.40 (18)C14B—C13B—C16B—C17B−105.7 (2)
C12A—C13A—C16A—C17A73.5 (2)C13B—C16B—C17B—C19B54.1 (3)
C14A—C13A—C16A—C17A−103.5 (2)C17C—C16B—C17B—C19B−47.5 (10)
C13A—C16A—C17A—C18A61.8 (2)C13B—C16B—C17B—C18B177.4 (2)
C13A—C16A—C17A—C19A−174.92 (18)C17C—C16B—C17B—C18B75.9 (10)
C7B—N1B—N2B—C8B172.53 (17)C13B—C16B—C17C—C19C−52.6 (12)
C6B—C1B—C2B—C3B−1.7 (3)C17B—C16B—C17C—C19C39.9 (10)
C1B—C2B—C3B—C4B2.2 (3)C13B—C16B—C17C—C18C−177.6 (7)
C1B—C2B—C3B—Cl1B−178.93 (15)C17B—C16B—C17C—C18C−85.1 (13)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2A—H1NA···O1B0.862.022.821 (2)155
C7A—H7AA···O1B0.932.543.313 (2)140
C12A—H12A···Cg10.932.753.632 (2)159
N2B—H1NB···O1Ai0.862.022.832 (2)157
C7B—H7BA···O1Ai0.932.473.256 (2)143
C12B—H12B···Cg2i0.932.653.462 (2)146
C20A—H20B···N1Bii0.962.573.504 (3)164

Symmetry codes: (i) x−1, y, z; (ii) −x+1, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2793).

References

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