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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o254–o255.
Published online 2010 January 9. doi:  10.1107/S1600536809054683
PMCID: PMC2979838

(E)-1-(4-Chloro­phen­yl)-3-[4-(diethyl­amino)phen­yl]prop-2-en-1-one1

Abstract

The asymmetric unit of the title chalcone derivative, C19H20ClNO, contains two independent mol­ecules, which differ in the conformations of the ethyl groups in the diethyl­amino substituents. In the crystal, weak inter­molecular C—H(...)O hydrogen bonds link mol­ecules into ribbons propogating in [010]. The crystal packing also exhibits weak C—H(...)π inter­actions.

Related literature

For bond-length data, see: Allen et al. (1987 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For related structures, see: Chantrapromma et al. (2009 [triangle]); Fun et al. (2009 [triangle]); Suwunwong et al. (2009 [triangle]). For background to and applications of chalcones, see: Svetlichny et al. (2007 [triangle]); Xu et al. (2005 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o254-scheme1.jpg

Experimental

Crystal data

  • C19H20ClNO
  • M r = 313.81
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o254-efi1.jpg
  • a = 17.2073 (2) Å
  • b = 11.9467 (1) Å
  • c = 15.7996 (2) Å
  • β = 97.268 (1)°
  • V = 3221.84 (6) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 100 K
  • 0.33 × 0.23 × 0.10 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.925, T max = 0.977
  • 47596 measured reflections
  • 9400 independent reflections
  • 6241 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.122
  • S = 1.10
  • 9400 reflections
  • 401 parameters
  • H-atom parameters constrained
  • Δρmax = 0.32 e Å−3
  • Δρmin = −0.35 e Å−3

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
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054683/cv2675sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054683/cv2675Isup2.hkl

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

Acknowledgments

TK thanks the Graduate School, Prince of Songkla University, for partial financial support. The authors thank Prince of Songkla University for financial support through the Crystal Materials Research Unit. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

supplementary crystallographic information

Comment

In continuation of our study of chalcone derivatives (Chantrapromma et al., 2009; Fun et al., 2009; Suwunwong et al., 2009) which can be used for fluorescence probe for sensing of DNA or proteins (Svetlichny et al., 2007; Xu et al., 2005), the title compound (I) was synthesized and its fluorescence with the maximum emission at 437 nm was measured. We report here its crystal structure.

The asymmetric unit of (I) contains two molecules, A and B, respectively, which differ in conformations of the ethyl groups of the diethylamino substituents. In molecule A, two ethyl groups are on the same side of the molecular plane, while they are on opposite sides in molecule B (Fig. 1). The bond lengths and bond angles in the two molecules are also slightly different. The molecules of (I) (Fig. 1) exist in an E configuration with respect to the C8═C9 double bond [1.349 (2) Å in molecule A and 1.341 (2) Å in molecule B] and the torsion angle C7–C8–C9–C10 is -178.39 (14)° in molecule A and 176.11 (4)° in molecule B. Two benzene rings are twisted at 16.27 (7)° in molecule A [16.99 (7) ° in molecule B]. The prop-2-en-1-one unit (C7–C9/O1) is planar with the rms 0.0066 (2) Å for molecule A [0.0116 (2) Å for molecule B]. The mean plane through the pro-2-en-1-one unit makes the dihedral angles of 19.02 (10) and 3.43 (10)° with the C1–C6 and C10–C15 benzene rings, respectively in molecule A [the corresponding values are 9.94 (10) and 7.31 (10)° in molecule B]. Two ethyl groups of the diethylamino substituent in molecule A are on the same side with the torsion angles C13A–N1A–C16A–C17A = -78.38 (18)° and C13A–N1A–C18A–C19A = 81.27 (18)° indicating the (-)-syn-clinal and (+)-syn-clinal conformations, respectively; whereas in molecule B, the two ethyl groups are on the opposite sides with the torsion angles C13B–N1B–C16B–C17B = 99.04 (17)° and C13B–N1B–C18B–C19B = 84.38 (17)° indicating the (+)-anti-clinal and (+)-syn-clinal conformations, respectively. Weak intramolecular C9A—H9AA···O1A, C5B—H5BA···O1B and C9B—H9BA···O1B hydrogen bonds generate S(5) ring motifs (Bernstein et al., 1995). The bond distances in (I) are of normal values (Allen et al., 1987) and are comparable with those in the related structure (Chantrapromma et al., 2009).

In the crystal (Fig. 2), the 4-chlorophenyl and the pro-2-en-1-one units of the molecules are linked by weak intermolecular C—H···O hydrogen bonds (Table 1) resulting in the molecules being connected into ribbons propagating along the [0 1 0] direction. The crystal packing exhibits also weak C—H···π interactions (Table 1); Cg1 is the centroid of the C10B–C15B ring.

Experimental

The title compound was synthesized by the condensation of 4-chloroacetophenone (0.40 g, 3 mmol) with 4-diethylaminobenzaldehyde (0.5 g, 3 mmol) in ethanol (20 ml) in the presence of 20% NaOH (aq) (5 ml). After stirring for 3 hr at 278 K, the resulting yellow solid was obtained and then collected by filtration, washed with distilled diethyl ether, dried and purified by repeated recrystallization from acetone. Yellow block-shaped single crystals of the title compound suitable for x-ray structure determination were recrystalized from methanol by the slow evaporation of the solvent at room temperature after several days, Mp. 374-375 K.

Refinement

All H atoms were positioned geometrically and allowed to ride on their parent atoms, with d(C-H) = 0.93 Å for aromatic and CH, 0.97 Å for CH2 and 0.96 Å for CH3 atoms. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups. The highest residual electron density peak is located at 0.68 Å from C6B and the deepest hole is located at 0.65 Å from Cl1B.

Figures

Fig. 1.
Two independent molecules of the title compound, with 50% probability displacement ellipsoids and the atom-numbering scheme.
Fig. 2.
The crystal packing of the title compound view along the a-axis, showing ribbons running along the b axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C19H20ClNOF(000) = 1328
Mr = 313.81Dx = 1.294 Mg m3
Monoclinic, P21/cMelting point = 374–375 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 17.2073 (2) ÅCell parameters from 9400 reflections
b = 11.9467 (1) Åθ = 1.9–30.0°
c = 15.7996 (2) ŵ = 0.24 mm1
β = 97.268 (1)°T = 100 K
V = 3221.84 (6) Å3Block, yellow
Z = 80.33 × 0.23 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer9400 independent reflections
Radiation source: sealed tube6241 reflections with I > 2σ(I)
graphiteRint = 0.041
[var phi] and ω scansθmax = 30.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −23→24
Tmin = 0.925, Tmax = 0.977k = −12→16
47596 measured reflectionsl = −21→22

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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.0474P)2 + 0.7024P] where P = (Fo2 + 2Fc2)/3
9400 reflections(Δ/σ)max = 0.001
401 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = −0.35 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems 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*/Ueq
Cl1A1.33545 (2)0.22869 (4)0.37652 (3)0.02632 (11)
O1A1.00783 (6)−0.07143 (9)0.29241 (7)0.0250 (3)
N1A0.62274 (7)0.22634 (11)−0.01499 (8)0.0220 (3)
C1A1.11964 (9)0.17759 (13)0.25803 (10)0.0203 (3)
H1AA1.08590.21190.21510.024*
C2A1.19351 (9)0.22284 (13)0.28205 (10)0.0209 (3)
H2AA1.20990.28570.25440.025*
C3A1.24235 (9)0.17306 (13)0.34767 (10)0.0193 (3)
C4A1.21866 (9)0.07958 (13)0.38999 (10)0.0216 (3)
H4AA1.25130.04840.43530.026*
C5A1.14600 (9)0.03364 (13)0.36369 (10)0.0208 (3)
H5AA1.1305−0.03040.39060.025*
C6A1.09523 (9)0.08156 (13)0.29733 (10)0.0186 (3)
C7A1.01754 (9)0.02632 (13)0.27110 (10)0.0185 (3)
C8A0.95504 (9)0.09153 (13)0.22182 (10)0.0197 (3)
H8AA0.96400.16590.20860.024*
C9A0.88478 (9)0.04481 (13)0.19551 (9)0.0193 (3)
H9AA0.8786−0.02910.21180.023*
C10A0.81767 (9)0.09526 (13)0.14509 (10)0.0190 (3)
C11A0.81717 (9)0.20500 (13)0.11330 (10)0.0208 (3)
H11A0.86110.24980.12720.025*
C12A0.75375 (9)0.24823 (13)0.06228 (10)0.0215 (4)
H12A0.75600.32140.04270.026*
C13A0.68503 (9)0.18439 (13)0.03865 (10)0.0194 (3)
C14A0.68454 (9)0.07499 (13)0.07266 (10)0.0220 (4)
H14A0.64000.03080.06060.026*
C15A0.74903 (9)0.03261 (13)0.12349 (10)0.0207 (3)
H15A0.7469−0.04010.14410.025*
C16A0.62152 (9)0.34250 (13)−0.04343 (10)0.0236 (4)
H16A0.58410.3495−0.09450.028*
H16B0.67280.3615−0.05860.028*
C17A0.60016 (10)0.42641 (14)0.02253 (11)0.0268 (4)
H17A0.60490.50110.00130.040*
H17B0.63490.41730.07460.040*
H17C0.54720.41370.03330.040*
C18A0.55139 (9)0.16108 (14)−0.03719 (10)0.0231 (4)
H18A0.56580.0839−0.04620.028*
H18B0.52440.1890−0.09060.028*
C19A0.49514 (10)0.16418 (15)0.02990 (11)0.0290 (4)
H19A0.44990.11940.01120.043*
H19B0.47920.24000.03800.043*
H19C0.52090.13510.08280.043*
Cl1B0.16956 (2)0.81186 (4)0.18284 (3)0.03390 (13)
O1B0.51160 (6)1.07982 (9)0.24066 (8)0.0283 (3)
N1B0.90996 (7)0.73741 (11)0.47926 (8)0.0193 (3)
C1B0.40036 (9)0.82319 (13)0.25395 (10)0.0209 (3)
H1BA0.44010.77290.27260.025*
C2B0.32374 (9)0.78546 (14)0.23590 (10)0.0227 (4)
H2BA0.31210.71020.24250.027*
C3B0.26505 (9)0.86039 (14)0.20805 (10)0.0221 (4)
C4B0.28072 (9)0.97338 (14)0.19930 (10)0.0250 (4)
H4BA0.24051.02340.18160.030*
C5B0.35717 (9)1.01030 (13)0.21739 (10)0.0217 (3)
H5BA0.36821.08590.21150.026*
C6B0.41803 (9)0.93639 (13)0.24428 (9)0.0176 (3)
C7B0.49926 (9)0.98249 (13)0.26100 (10)0.0189 (3)
C8B0.56250 (9)0.91209 (13)0.30276 (10)0.0207 (3)
H8BA0.55120.84040.32060.025*
C9B0.63645 (9)0.94976 (13)0.31555 (9)0.0187 (3)
H9BA0.64471.02010.29320.022*
C10B0.70517 (9)0.89533 (13)0.35960 (10)0.0180 (3)
C11B0.70277 (9)0.79079 (13)0.39960 (10)0.0200 (3)
H11B0.65470.75510.39920.024*
C12B0.76888 (9)0.73904 (13)0.43942 (10)0.0196 (3)
H12B0.76450.66990.46550.023*
C13B0.84368 (9)0.78947 (13)0.44136 (9)0.0173 (3)
C14B0.84647 (9)0.89580 (13)0.40271 (10)0.0186 (3)
H14B0.89430.93220.40340.022*
C15B0.77899 (9)0.94644 (13)0.36396 (10)0.0189 (3)
H15B0.78261.01700.33990.023*
C16B0.98874 (9)0.77527 (13)0.46801 (10)0.0198 (3)
H16C0.98610.81850.41570.024*
H16D1.02150.71040.46190.024*
C17B1.02667 (9)0.84630 (14)0.54171 (11)0.0251 (4)
H17D1.07950.86370.53290.038*
H17E1.02690.80560.59410.038*
H17F0.99750.91440.54460.038*
C18B0.90602 (9)0.63347 (13)0.52717 (10)0.0209 (3)
H18C0.86060.63590.55780.025*
H18D0.95230.62760.56890.025*
C19B0.90064 (10)0.53012 (14)0.47043 (11)0.0259 (4)
H19D0.90300.46410.50530.039*
H19E0.94350.52980.43700.039*
H19F0.85200.53120.43320.039*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl1A0.0194 (2)0.0273 (2)0.0314 (2)−0.00409 (16)−0.00011 (16)0.00009 (18)
O1A0.0213 (6)0.0216 (6)0.0316 (7)−0.0014 (5)0.0018 (5)0.0073 (5)
N1A0.0195 (7)0.0215 (7)0.0240 (7)0.0001 (6)−0.0012 (6)0.0034 (6)
C1A0.0200 (8)0.0212 (9)0.0196 (8)0.0020 (7)0.0013 (6)0.0031 (7)
C2A0.0223 (8)0.0182 (8)0.0228 (8)−0.0009 (7)0.0049 (7)0.0011 (7)
C3A0.0166 (7)0.0190 (9)0.0221 (8)−0.0004 (6)0.0016 (6)−0.0023 (7)
C4A0.0209 (8)0.0204 (9)0.0227 (8)0.0043 (7)−0.0001 (7)0.0013 (7)
C5A0.0219 (8)0.0165 (8)0.0241 (8)0.0017 (6)0.0039 (7)0.0035 (7)
C6A0.0198 (8)0.0173 (8)0.0192 (8)0.0016 (6)0.0040 (6)0.0000 (6)
C7A0.0189 (8)0.0200 (9)0.0173 (8)0.0004 (6)0.0048 (6)0.0003 (6)
C8A0.0205 (8)0.0175 (8)0.0214 (8)0.0006 (6)0.0035 (6)0.0017 (6)
C9A0.0218 (8)0.0185 (8)0.0185 (8)0.0012 (6)0.0053 (6)0.0000 (6)
C10A0.0193 (8)0.0185 (9)0.0193 (8)0.0009 (6)0.0033 (6)−0.0008 (6)
C11A0.0171 (8)0.0203 (9)0.0251 (8)−0.0018 (6)0.0034 (6)−0.0019 (7)
C12A0.0213 (8)0.0166 (9)0.0271 (9)0.0009 (6)0.0054 (7)0.0030 (7)
C13A0.0194 (8)0.0199 (9)0.0191 (8)0.0008 (6)0.0031 (6)−0.0003 (6)
C14A0.0205 (8)0.0188 (9)0.0258 (9)−0.0027 (7)0.0003 (7)−0.0009 (7)
C15A0.0229 (8)0.0154 (8)0.0231 (8)−0.0007 (6)0.0010 (7)0.0007 (6)
C16A0.0236 (8)0.0234 (9)0.0230 (8)0.0002 (7)−0.0007 (7)0.0072 (7)
C17A0.0237 (9)0.0243 (10)0.0328 (10)−0.0003 (7)0.0046 (7)0.0045 (7)
C18A0.0226 (8)0.0231 (9)0.0219 (8)−0.0012 (7)−0.0039 (7)−0.0011 (7)
C19A0.0265 (9)0.0285 (10)0.0317 (10)−0.0065 (8)0.0029 (8)−0.0009 (8)
Cl1B0.0241 (2)0.0341 (3)0.0408 (3)−0.00895 (18)−0.00643 (19)0.0077 (2)
O1B0.0260 (6)0.0199 (7)0.0384 (7)−0.0013 (5)0.0015 (5)0.0073 (5)
N1B0.0173 (7)0.0173 (7)0.0232 (7)−0.0002 (5)0.0016 (5)0.0041 (5)
C1B0.0232 (8)0.0174 (9)0.0222 (8)0.0044 (7)0.0032 (7)0.0003 (7)
C2B0.0281 (9)0.0155 (8)0.0243 (8)−0.0030 (7)0.0022 (7)−0.0006 (7)
C3B0.0204 (8)0.0231 (9)0.0222 (8)−0.0033 (7)0.0002 (7)0.0008 (7)
C4B0.0239 (9)0.0219 (9)0.0281 (9)0.0042 (7)−0.0014 (7)0.0018 (7)
C5B0.0251 (9)0.0147 (8)0.0247 (9)−0.0005 (7)0.0005 (7)0.0000 (7)
C6B0.0207 (8)0.0170 (8)0.0153 (7)0.0013 (6)0.0027 (6)−0.0012 (6)
C7B0.0213 (8)0.0178 (9)0.0178 (8)0.0004 (6)0.0029 (6)0.0002 (6)
C8B0.0226 (8)0.0164 (8)0.0229 (8)0.0008 (6)0.0025 (7)0.0029 (7)
C9B0.0217 (8)0.0160 (8)0.0191 (8)0.0017 (6)0.0049 (6)−0.0015 (6)
C10B0.0189 (8)0.0163 (8)0.0194 (8)0.0014 (6)0.0050 (6)−0.0017 (6)
C11B0.0170 (8)0.0198 (9)0.0242 (8)−0.0012 (6)0.0063 (6)−0.0025 (7)
C12B0.0215 (8)0.0151 (8)0.0225 (8)−0.0005 (6)0.0045 (6)0.0006 (6)
C13B0.0188 (8)0.0166 (8)0.0166 (7)0.0004 (6)0.0028 (6)−0.0021 (6)
C14B0.0176 (8)0.0174 (8)0.0209 (8)−0.0032 (6)0.0030 (6)−0.0024 (6)
C15B0.0229 (8)0.0143 (8)0.0202 (8)0.0008 (6)0.0054 (6)−0.0011 (6)
C16B0.0172 (8)0.0197 (8)0.0229 (8)0.0010 (6)0.0036 (6)0.0013 (7)
C17B0.0201 (8)0.0257 (9)0.0288 (9)−0.0012 (7)0.0002 (7)−0.0004 (7)
C18B0.0199 (8)0.0207 (9)0.0218 (8)0.0003 (7)0.0010 (6)0.0041 (7)
C19B0.0254 (9)0.0198 (9)0.0314 (9)0.0011 (7)−0.0007 (7)0.0020 (7)

Geometric parameters (Å, °)

Cl1A—C3A1.7411 (15)Cl1B—C3B1.7405 (16)
O1A—C7A1.2326 (18)O1B—C7B1.2320 (18)
N1A—C13A1.3741 (19)N1B—C13B1.3687 (19)
N1A—C16A1.458 (2)N1B—C18B1.460 (2)
N1A—C18A1.459 (2)N1B—C16B1.4610 (19)
C1A—C2A1.389 (2)C1B—C2B1.388 (2)
C1A—C6A1.394 (2)C1B—C6B1.399 (2)
C1A—H1AA0.9300C1B—H1BA0.9300
C2A—C3A1.384 (2)C2B—C3B1.379 (2)
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.389 (2)C3B—C4B1.387 (2)
C4A—C5A1.381 (2)C4B—C5B1.383 (2)
C4A—H4AA0.9300C4B—H4BA0.9300
C5A—C6A1.399 (2)C5B—C6B1.394 (2)
C5A—H5AA0.9300C5B—H5BA0.9300
C6A—C7A1.501 (2)C6B—C7B1.495 (2)
C7A—C8A1.469 (2)C7B—C8B1.465 (2)
C8A—C9A1.349 (2)C8B—C9B1.341 (2)
C8A—H8AA0.9300C8B—H8BA0.9300
C9A—C10A1.449 (2)C9B—C10B1.448 (2)
C9A—H9AA0.9300C9B—H9BA0.9300
C10A—C15A1.404 (2)C10B—C11B1.403 (2)
C10A—C11A1.404 (2)C10B—C15B1.403 (2)
C11A—C12A1.373 (2)C11B—C12B1.375 (2)
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.417 (2)C12B—C13B1.418 (2)
C12A—H12A0.9300C12B—H12B0.9300
C13A—C14A1.414 (2)C13B—C14B1.413 (2)
C14A—C15A1.381 (2)C14B—C15B1.382 (2)
C14A—H14A0.9300C14B—H14B0.9300
C15A—H15A0.9300C15B—H15B0.9300
C16A—C17A1.524 (2)C16B—C17B1.520 (2)
C16A—H16A0.9700C16B—H16C0.9700
C16A—H16B0.9700C16B—H16D0.9700
C17A—H17A0.9600C17B—H17D0.9600
C17A—H17B0.9600C17B—H17E0.9600
C17A—H17C0.9600C17B—H17F0.9600
C18A—C19A1.524 (2)C18B—C19B1.522 (2)
C18A—H18A0.9700C18B—H18C0.9700
C18A—H18B0.9700C18B—H18D0.9700
C19A—H19A0.9600C19B—H19D0.9600
C19A—H19B0.9600C19B—H19E0.9600
C19A—H19C0.9600C19B—H19F0.9600
C13A—N1A—C16A121.13 (13)C13B—N1B—C18B121.49 (12)
C13A—N1A—C18A121.34 (13)C13B—N1B—C16B122.73 (13)
C16A—N1A—C18A117.10 (12)C18B—N1B—C16B115.52 (12)
C2A—C1A—C6A121.02 (14)C2B—C1B—C6B120.35 (14)
C2A—C1A—H1AA119.5C2B—C1B—H1BA119.8
C6A—C1A—H1AA119.5C6B—C1B—H1BA119.8
C3A—C2A—C1A119.04 (15)C3B—C2B—C1B119.53 (15)
C3A—C2A—H2AA120.5C3B—C2B—H2BA120.2
C1A—C2A—H2AA120.5C1B—C2B—H2BA120.2
C2A—C3A—C4A121.26 (14)C2B—C3B—C4B121.31 (15)
C2A—C3A—Cl1A118.93 (12)C2B—C3B—Cl1B119.26 (13)
C4A—C3A—Cl1A119.81 (12)C4B—C3B—Cl1B119.42 (12)
C5A—C4A—C3A118.98 (15)C5B—C4B—C3B118.81 (15)
C5A—C4A—H4AA120.5C5B—C4B—H4BA120.6
C3A—C4A—H4AA120.5C3B—C4B—H4BA120.6
C4A—C5A—C6A121.24 (15)C4B—C5B—C6B121.27 (15)
C4A—C5A—H5AA119.4C4B—C5B—H5BA119.4
C6A—C5A—H5AA119.4C6B—C5B—H5BA119.4
C1A—C6A—C5A118.40 (14)C5B—C6B—C1B118.71 (14)
C1A—C6A—C7A123.13 (14)C5B—C6B—C7B118.04 (14)
C5A—C6A—C7A118.47 (14)C1B—C6B—C7B123.26 (14)
O1A—C7A—C8A122.12 (14)O1B—C7B—C8B121.12 (14)
O1A—C7A—C6A119.20 (14)O1B—C7B—C6B119.33 (14)
C8A—C7A—C6A118.68 (14)C8B—C7B—C6B119.54 (14)
C9A—C8A—C7A120.77 (15)C9B—C8B—C7B120.80 (15)
C9A—C8A—H8AA119.6C9B—C8B—H8BA119.6
C7A—C8A—H8AA119.6C7B—C8B—H8BA119.6
C8A—C9A—C10A128.20 (15)C8B—C9B—C10B128.56 (15)
C8A—C9A—H9AA115.9C8B—C9B—H9BA115.7
C10A—C9A—H9AA115.9C10B—C9B—H9BA115.7
C15A—C10A—C11A116.37 (14)C11B—C10B—C15B116.32 (14)
C15A—C10A—C9A119.98 (14)C11B—C10B—C9B123.19 (14)
C11A—C10A—C9A123.63 (14)C15B—C10B—C9B120.48 (14)
C12A—C11A—C10A122.00 (14)C12B—C11B—C10B122.45 (14)
C12A—C11A—H11A119.0C12B—C11B—H11B118.8
C10A—C11A—H11A119.0C10B—C11B—H11B118.8
C11A—C12A—C13A121.81 (15)C11B—C12B—C13B121.00 (14)
C11A—C12A—H12A119.1C11B—C12B—H12B119.5
C13A—C12A—H12A119.1C13B—C12B—H12B119.5
N1A—C13A—C14A122.01 (14)N1B—C13B—C14B121.71 (14)
N1A—C13A—C12A121.73 (14)N1B—C13B—C12B121.35 (14)
C14A—C13A—C12A116.25 (14)C14B—C13B—C12B116.93 (14)
C15A—C14A—C13A121.14 (14)C15B—C14B—C13B120.84 (14)
C15A—C14A—H14A119.4C15B—C14B—H14B119.6
C13A—C14A—H14A119.4C13B—C14B—H14B119.6
C14A—C15A—C10A122.38 (15)C14B—C15B—C10B122.41 (14)
C14A—C15A—H15A118.8C14B—C15B—H15B118.8
C10A—C15A—H15A118.8C10B—C15B—H15B118.8
N1A—C16A—C17A114.24 (13)N1B—C16B—C17B113.25 (13)
N1A—C16A—H16A108.7N1B—C16B—H16C108.9
C17A—C16A—H16A108.7C17B—C16B—H16C108.9
N1A—C16A—H16B108.7N1B—C16B—H16D108.9
C17A—C16A—H16B108.7C17B—C16B—H16D108.9
H16A—C16A—H16B107.6H16C—C16B—H16D107.7
C16A—C17A—H17A109.5C16B—C17B—H17D109.5
C16A—C17A—H17B109.5C16B—C17B—H17E109.5
H17A—C17A—H17B109.5H17D—C17B—H17E109.5
C16A—C17A—H17C109.5C16B—C17B—H17F109.5
H17A—C17A—H17C109.5H17D—C17B—H17F109.5
H17B—C17A—H17C109.5H17E—C17B—H17F109.5
N1A—C18A—C19A114.14 (13)N1B—C18B—C19B112.83 (13)
N1A—C18A—H18A108.7N1B—C18B—H18C109.0
C19A—C18A—H18A108.7C19B—C18B—H18C109.0
N1A—C18A—H18B108.7N1B—C18B—H18D109.0
C19A—C18A—H18B108.7C19B—C18B—H18D109.0
H18A—C18A—H18B107.6H18C—C18B—H18D107.8
C18A—C19A—H19A109.5C18B—C19B—H19D109.5
C18A—C19A—H19B109.5C18B—C19B—H19E109.5
H19A—C19A—H19B109.5H19D—C19B—H19E109.5
C18A—C19A—H19C109.5C18B—C19B—H19F109.5
H19A—C19A—H19C109.5H19D—C19B—H19F109.5
H19B—C19A—H19C109.5H19E—C19B—H19F109.5
C6A—C1A—C2A—C3A−1.8 (2)C6B—C1B—C2B—C3B0.2 (2)
C1A—C2A—C3A—C4A−0.4 (2)C1B—C2B—C3B—C4B−1.3 (2)
C1A—C2A—C3A—Cl1A179.03 (12)C1B—C2B—C3B—Cl1B178.31 (12)
C2A—C3A—C4A—C5A2.3 (2)C2B—C3B—C4B—C5B1.3 (2)
Cl1A—C3A—C4A—C5A−177.11 (12)Cl1B—C3B—C4B—C5B−178.31 (12)
C3A—C4A—C5A—C6A−2.0 (2)C3B—C4B—C5B—C6B−0.2 (2)
C2A—C1A—C6A—C5A2.1 (2)C4B—C5B—C6B—C1B−0.9 (2)
C2A—C1A—C6A—C7A−177.12 (14)C4B—C5B—C6B—C7B178.88 (14)
C4A—C5A—C6A—C1A−0.1 (2)C2B—C1B—C6B—C5B0.9 (2)
C4A—C5A—C6A—C7A179.12 (14)C2B—C1B—C6B—C7B−178.86 (14)
C1A—C6A—C7A—O1A161.56 (15)C5B—C6B—C7B—O1B−9.0 (2)
C5A—C6A—C7A—O1A−17.6 (2)C1B—C6B—C7B—O1B170.70 (15)
C1A—C6A—C7A—C8A−19.4 (2)C5B—C6B—C7B—C8B169.77 (14)
C5A—C6A—C7A—C8A161.42 (14)C1B—C6B—C7B—C8B−10.5 (2)
O1A—C7A—C8A—C9A−2.2 (2)O1B—C7B—C8B—C9B−3.8 (2)
C6A—C7A—C8A—C9A178.77 (14)C6B—C7B—C8B—C9B177.38 (14)
C7A—C8A—C9A—C10A−178.39 (14)C7B—C8B—C9B—C10B176.11 (14)
C8A—C9A—C10A—C15A179.71 (15)C8B—C9B—C10B—C11B−2.2 (3)
C8A—C9A—C10A—C11A1.6 (3)C8B—C9B—C10B—C15B177.64 (15)
C15A—C10A—C11A—C12A−1.4 (2)C15B—C10B—C11B—C12B−1.5 (2)
C9A—C10A—C11A—C12A176.80 (15)C9B—C10B—C11B—C12B178.41 (14)
C10A—C11A—C12A—C13A−0.1 (2)C10B—C11B—C12B—C13B−0.4 (2)
C16A—N1A—C13A—C14A174.59 (14)C18B—N1B—C13B—C14B173.21 (14)
C18A—N1A—C13A—C14A2.3 (2)C16B—N1B—C13B—C14B−12.8 (2)
C16A—N1A—C13A—C12A−6.0 (2)C18B—N1B—C13B—C12B−6.6 (2)
C18A—N1A—C13A—C12A−178.37 (14)C16B—N1B—C13B—C12B167.43 (14)
C11A—C12A—C13A—N1A−177.54 (14)C11B—C12B—C13B—N1B−178.57 (14)
C11A—C12A—C13A—C14A1.9 (2)C11B—C12B—C13B—C14B1.6 (2)
N1A—C13A—C14A—C15A177.16 (15)N1B—C13B—C14B—C15B179.29 (14)
C12A—C13A—C14A—C15A−2.2 (2)C12B—C13B—C14B—C15B−0.9 (2)
C13A—C14A—C15A—C10A0.8 (2)C13B—C14B—C15B—C10B−1.0 (2)
C11A—C10A—C15A—C14A1.0 (2)C11B—C10B—C15B—C14B2.2 (2)
C9A—C10A—C15A—C14A−177.26 (14)C9B—C10B—C15B—C14B−177.68 (14)
C13A—N1A—C16A—C17A−78.38 (18)C13B—N1B—C16B—C17B99.04 (17)
C18A—N1A—C16A—C17A94.27 (16)C18B—N1B—C16B—C17B−86.63 (16)
C13A—N1A—C18A—C19A81.27 (18)C13B—N1B—C18B—C19B84.38 (17)
C16A—N1A—C18A—C19A−91.36 (17)C16B—N1B—C18B—C19B−90.03 (16)

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10B–C15B ring.
D—H···AD—HH···AD···AD—H···A
C1B—H1BA···O1Bi0.932.473.2746 (19)145
C16B—H16C···O1Aii0.972.423.3749 (19)168
C2A—H2AA···Cg1iii0.932.603.3377 (17)137

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

Footnotes

1This paper is dedicated to His Majesty King Bhumibol Adulyadej of Thailand (King Rama IX) on the occasion of his 82th Birthday Anniversary which fell on December 5th, 2009.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2675).

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