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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

3-(3,4-Di­chloro­phen­yl)-1-(2-naphth­yl)prop-2-en-1-one

aForestry College, Guangxi University, Nanning 530005, People's Republic of China, and bChemistry Department, Guangxi Industrial Vocational Technical College, Nanning 530001, People's Republic of China
*Correspondence e-mail: lukz1886@yahoo.com.cn

(Received 13 August 2009; accepted 25 August 2009; online 29 August 2009)

The asymmetric unit of the title compound, C19H12Cl2O, contains four independent mol­ecules, which can be divided into two pairs of mol­ecules with close values of the C—C(=O)—C=C torsion angles in each pair, viz. 165.12 (16) and 165.68 (15)° in one pair, and −164.66 (15) and −164.81 (15)° in the other pair. The crystal packing exhibits short inter­molecular Cl⋯Cl contacts of 3.362 (1) Å.

Related literature

For a related structure, see Lu et al. (2006[Lu, Z.-K., Huang, P.-M. & Yu, J.-F. (2006). Acta Cryst. E62, o5753-o5754.]).

[Scheme 1]

Experimental

Crystal data
  • C19H12Cl2O

  • Mr = 327.19

  • Triclinic, [P \overline 1]

  • a = 7.5273 (10) Å

  • b = 11.5212 (14) Å

  • c = 33.301 (4) Å

  • α = 92.338 (7)°

  • β = 96.469 (7)°

  • γ = 90.125 (6)°

  • V = 2867.1 (6) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.45 mm−1

  • T = 113 K

  • 0.36 × 0.34 × 0.28 mm

Data collection
  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.855, Tmax = 0.884

  • 26590 measured reflections

  • 13067 independent reflections

  • 10135 reflections with I > 2σ(I)

  • Rint = 0.023

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.106

  • S = 1.07

  • 13067 reflections

  • 793 parameters

  • H-atom parameters constrained

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.44 e Å−3

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004[Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]).

Supporting information


Comment top

The title compound, (I), (Fig. 1) was prepared and structurally characterized as a part of our ongoing studies of pyrazoline derivatives (Lu et al., 2006).

Related literature top

For a related structure, see Lu et al. (2006).

Experimental top

A mixture of 3,4-dichlorobenzaldehyde(5 mmol) and 2-(prop-1-en-2-yl) naphthalene benzaldehyde (10 mmol) was dissolved in aqueous ethanol (100 ml, 60% v/v). The solution of KOH (4.0 ml, 7.1 mmol) was slowly added and stirred at 323 K for 5 h. The resulting mixture was neutralized with 2 N HCl. The precipitate filtered off, washed with water, and crystallized from dichloromethane-methanol (1/4 v/v) to obtain (I) (m.p.426–427k). Crystals suitable for X-ray analysis were grown by slow evaporation of a methanol-dichloromethane (4/1 v/v) solution at room temperature over a period of 16 d.

Refinement top

All H atoms were placed geometrically (C—H = 0.95 Å), and refined as riding with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004).

Figures top
[Figure 1] Fig. 1. Four independent molecules of (I), shown with 30% probability displacement ellipsoids (arbitrary spheres for H atoms).
3-(3,4-Dichlorophenyl)-1-(2-naphthyl)prop-2-en-1-one top
Crystal data top
C19H12Cl2OZ = 8
Mr = 327.19F(000) = 1344
Triclinic, P1Dx = 1.516 Mg m3
Hall symbol: -P 1Melting point: 426-427 K K
a = 7.5273 (10) ÅMo Kα radiation, λ = 0.71070 Å
b = 11.5212 (14) ÅCell parameters from 4591 reflections
c = 33.301 (4) Åθ = 1.2–27.2°
α = 92.338 (7)°µ = 0.45 mm1
β = 96.469 (7)°T = 113 K
γ = 90.125 (6)°Block, yellow
V = 2867.1 (6) Å30.36 × 0.34 × 0.28 mm
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
13067 independent reflections
Radiation source: Rotating anode10135 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.023
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 1.9°
ω and ϕ scansh = 99
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 1514
Tmin = 0.855, Tmax = 0.884l = 4343
26590 measured reflections
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0577P)2 + 0.5613P]
where P = (Fo2 + 2Fc2)/3
13067 reflections(Δ/σ)max = 0.001
793 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.44 e Å3
Crystal data top
C19H12Cl2Oγ = 90.125 (6)°
Mr = 327.19V = 2867.1 (6) Å3
Triclinic, P1Z = 8
a = 7.5273 (10) ÅMo Kα radiation
b = 11.5212 (14) ŵ = 0.45 mm1
c = 33.301 (4) ÅT = 113 K
α = 92.338 (7)°0.36 × 0.34 × 0.28 mm
β = 96.469 (7)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
13067 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
10135 reflections with I > 2σ(I)
Tmin = 0.855, Tmax = 0.884Rint = 0.023
26590 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.106H-atom parameters constrained
S = 1.07Δρmax = 0.37 e Å3
13067 reflectionsΔρmin = 0.44 e Å3
793 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.00530 (6)0.47380 (4)0.209773 (11)0.02137 (10)
Cl20.18280 (6)0.22714 (4)0.206473 (12)0.02169 (10)
Cl30.48364 (6)0.02522 (3)0.207594 (11)0.02037 (9)
Cl40.32062 (6)0.22617 (3)0.204037 (11)0.02038 (9)
Cl50.80421 (6)0.47713 (3)0.292686 (11)0.02060 (9)
Cl60.97202 (6)0.22757 (4)0.295246 (12)0.02159 (10)
Cl70.29865 (6)0.02818 (3)0.291430 (11)0.02085 (9)
Cl80.47357 (6)0.22092 (3)0.293851 (12)0.02095 (9)
O10.27954 (17)0.60599 (10)0.01527 (3)0.0239 (3)
O20.78508 (17)0.10351 (10)0.01670 (3)0.0233 (3)
O30.73173 (17)0.60659 (10)0.51678 (3)0.0235 (3)
O40.23484 (17)0.10235 (10)0.51615 (3)0.0234 (3)
C10.2845 (2)0.50007 (14)0.01544 (5)0.0163 (3)
C20.2051 (2)0.42617 (14)0.01949 (5)0.0189 (3)
H20.18290.34610.01610.023*
C30.1646 (2)0.47136 (14)0.05569 (5)0.0165 (3)
H30.19380.55090.05800.020*
C40.0788 (2)0.40906 (13)0.09209 (4)0.0152 (3)
C50.0749 (2)0.46242 (14)0.12922 (5)0.0159 (3)
H50.12670.53740.13030.019*
C60.0041 (2)0.40647 (13)0.16443 (4)0.0153 (3)
C70.0807 (2)0.29715 (13)0.16304 (4)0.0156 (3)
C80.0789 (2)0.24368 (14)0.12628 (5)0.0168 (3)
H80.13280.16940.12530.020*
C90.0016 (2)0.29893 (13)0.09119 (5)0.0165 (3)
H90.00450.26160.06620.020*
C100.3765 (2)0.49862 (13)0.08884 (5)0.0147 (3)
H100.32810.57450.09070.018*
C110.3692 (2)0.44034 (13)0.05170 (4)0.0153 (3)
C120.4422 (2)0.32751 (14)0.04866 (5)0.0181 (3)
H120.43370.28650.02320.022*
C130.5251 (2)0.27731 (14)0.08231 (5)0.0177 (3)
H130.57810.20300.07970.021*
C140.5329 (2)0.33478 (13)0.12094 (5)0.0150 (3)
C150.4553 (2)0.44688 (13)0.12426 (5)0.0148 (3)
C160.4588 (2)0.50344 (14)0.16303 (5)0.0174 (3)
H160.40640.57790.16560.021*
C170.5371 (2)0.45125 (15)0.19667 (5)0.0204 (3)
H170.53880.48980.22250.024*
C180.6154 (2)0.34067 (15)0.19333 (5)0.0214 (4)
H180.66940.30540.21690.026*
C190.6144 (2)0.28379 (14)0.15648 (5)0.0187 (3)
H190.66850.20960.15460.022*
C200.7887 (2)0.00248 (14)0.01717 (5)0.0171 (3)
C210.7086 (2)0.06819 (14)0.01763 (5)0.0189 (3)
H210.68680.14900.01420.023*
C220.6668 (2)0.01464 (14)0.05379 (5)0.0165 (3)
H220.69530.06540.05620.020*
C230.5808 (2)0.06863 (13)0.09011 (4)0.0149 (3)
C240.5721 (2)0.00596 (13)0.12721 (5)0.0151 (3)
H240.62110.06990.12840.018*
C250.4922 (2)0.05398 (13)0.16234 (4)0.0153 (3)
C260.4207 (2)0.16467 (13)0.16086 (4)0.0154 (3)
C270.4271 (2)0.22752 (14)0.12403 (5)0.0167 (3)
H270.37650.30290.12300.020*
C280.5071 (2)0.18000 (14)0.08905 (5)0.0167 (3)
H280.51200.22340.06410.020*
C290.8808 (2)0.02162 (13)0.09061 (5)0.0149 (3)
H290.83270.05400.09250.018*
C300.8731 (2)0.07115 (13)0.05331 (4)0.0154 (3)
C310.9453 (2)0.18380 (14)0.05041 (5)0.0180 (3)
H310.93650.21880.02490.022*
C321.0276 (2)0.24257 (14)0.08396 (5)0.0172 (3)
H321.07990.31660.08140.021*
C331.0355 (2)0.19405 (13)0.12265 (5)0.0155 (3)
C340.9595 (2)0.08219 (13)0.12592 (4)0.0149 (3)
C350.9641 (2)0.03472 (14)0.16475 (5)0.0174 (3)
H350.91300.03970.16740.021*
C361.0415 (2)0.09555 (15)0.19838 (5)0.0215 (3)
H361.04330.06320.22420.026*
C371.1188 (2)0.20578 (15)0.19500 (5)0.0221 (4)
H371.17270.24700.21860.027*
C381.1168 (2)0.25401 (14)0.15806 (5)0.0190 (3)
H381.17020.32810.15610.023*
C390.7281 (2)0.50044 (14)0.51735 (5)0.0170 (3)
C400.7726 (2)0.42625 (14)0.48243 (5)0.0189 (3)
H400.79650.34610.48580.023*
C410.7792 (2)0.47129 (14)0.44642 (5)0.0164 (3)
H410.74980.55110.44410.020*
C420.8279 (2)0.40890 (13)0.40996 (4)0.0147 (3)
C430.7975 (2)0.46376 (13)0.37293 (5)0.0154 (3)
H430.74720.53930.37200.019*
C440.8410 (2)0.40780 (14)0.33775 (4)0.0154 (3)
C450.9157 (2)0.29754 (14)0.33880 (5)0.0157 (3)
C460.9474 (2)0.24305 (14)0.37545 (5)0.0168 (3)
H460.99950.16800.37630.020*
C470.9029 (2)0.29816 (14)0.41062 (5)0.0168 (3)
H470.92380.26020.43550.020*
C480.7104 (2)0.49980 (13)0.59074 (5)0.0149 (3)
H480.76080.57580.59240.018*
C490.6802 (2)0.44107 (13)0.55364 (4)0.0153 (3)
C500.6039 (2)0.32813 (14)0.55080 (5)0.0175 (3)
H500.58600.28690.52540.021*
C510.5557 (2)0.27817 (14)0.58458 (5)0.0177 (3)
H510.50060.20360.58220.021*
C520.5868 (2)0.33593 (13)0.62308 (5)0.0155 (3)
C530.6675 (2)0.44834 (13)0.62628 (5)0.0146 (3)
C540.7031 (2)0.50529 (14)0.66494 (5)0.0183 (3)
H540.75710.58020.66740.022*
C550.6602 (2)0.45286 (15)0.69874 (5)0.0213 (3)
H550.68560.49140.72450.026*
C560.5787 (2)0.34214 (15)0.69557 (5)0.0227 (4)
H560.54890.30680.71920.027*
C570.5420 (2)0.28511 (14)0.65881 (5)0.0192 (3)
H570.48610.21080.65710.023*
C580.2305 (2)0.00346 (14)0.51642 (5)0.0172 (3)
C590.2745 (2)0.06893 (14)0.48147 (5)0.0188 (3)
H590.29940.14980.48480.023*
C600.2794 (2)0.01502 (14)0.44534 (5)0.0168 (3)
H600.24900.06530.44310.020*
C610.3273 (2)0.06839 (13)0.40872 (4)0.0154 (3)
C620.2955 (2)0.00500 (14)0.37185 (5)0.0158 (3)
H620.24410.07060.37110.019*
C630.3385 (2)0.05196 (14)0.33638 (4)0.0158 (3)
C640.4154 (2)0.16158 (14)0.33743 (4)0.0158 (3)
C650.4487 (2)0.22523 (14)0.37399 (5)0.0169 (3)
H650.50180.30030.37470.020*
C660.4045 (2)0.17903 (13)0.40931 (5)0.0166 (3)
H660.42680.22290.43420.020*
C670.2121 (2)0.02260 (13)0.58983 (5)0.0149 (3)
H670.26230.05280.59170.018*
C680.1818 (2)0.07219 (13)0.55265 (4)0.0155 (3)
C690.1058 (2)0.18394 (14)0.54959 (5)0.0177 (3)
H690.08850.21870.52410.021*
C700.0567 (2)0.24240 (14)0.58322 (5)0.0172 (3)
H700.00120.31610.58060.021*
C710.0880 (2)0.19411 (13)0.62188 (5)0.0154 (3)
C720.1689 (2)0.08319 (13)0.62524 (4)0.0142 (3)
C730.2038 (2)0.03555 (14)0.66403 (5)0.0176 (3)
H730.25790.03860.66660.021*
C740.1598 (2)0.09629 (15)0.69779 (5)0.0208 (3)
H740.18460.06420.72360.025*
C750.0781 (2)0.20611 (15)0.69434 (5)0.0212 (3)
H750.04810.24730.71790.025*
C760.0416 (2)0.25385 (14)0.65738 (5)0.0185 (3)
H760.01510.32730.65540.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0263 (2)0.0234 (2)0.01441 (18)0.00252 (17)0.00050 (15)0.00574 (14)
Cl20.0233 (2)0.0231 (2)0.01752 (18)0.00437 (16)0.00162 (15)0.00247 (14)
Cl30.0270 (2)0.0200 (2)0.01394 (17)0.00279 (16)0.00222 (15)0.00196 (14)
Cl40.0227 (2)0.0206 (2)0.01712 (18)0.00368 (16)0.00198 (15)0.00331 (14)
Cl50.0267 (2)0.0216 (2)0.01365 (17)0.00192 (16)0.00179 (15)0.00411 (14)
Cl60.0249 (2)0.0224 (2)0.01806 (18)0.00308 (16)0.00624 (15)0.00309 (14)
Cl70.0281 (2)0.0203 (2)0.01389 (17)0.00261 (16)0.00228 (15)0.00151 (14)
Cl80.0238 (2)0.0222 (2)0.01798 (18)0.00305 (16)0.00538 (15)0.00522 (14)
O10.0347 (7)0.0173 (6)0.0191 (6)0.0015 (5)0.0002 (5)0.0021 (4)
O20.0332 (7)0.0174 (6)0.0184 (6)0.0001 (5)0.0009 (5)0.0001 (4)
O30.0353 (7)0.0173 (6)0.0183 (6)0.0016 (5)0.0048 (5)0.0015 (4)
O40.0342 (7)0.0177 (6)0.0183 (6)0.0009 (5)0.0041 (5)0.0002 (4)
C10.0172 (8)0.0176 (8)0.0142 (7)0.0026 (6)0.0023 (6)0.0018 (6)
C20.0214 (9)0.0175 (8)0.0176 (8)0.0031 (7)0.0007 (6)0.0010 (6)
C30.0161 (8)0.0168 (8)0.0165 (7)0.0007 (6)0.0013 (6)0.0000 (6)
C40.0131 (8)0.0165 (8)0.0160 (7)0.0014 (6)0.0017 (6)0.0011 (6)
C50.0140 (8)0.0157 (7)0.0180 (7)0.0008 (6)0.0018 (6)0.0015 (6)
C60.0146 (8)0.0180 (8)0.0136 (7)0.0017 (6)0.0022 (6)0.0036 (6)
C70.0137 (8)0.0176 (8)0.0151 (7)0.0013 (6)0.0008 (6)0.0015 (6)
C80.0170 (8)0.0142 (7)0.0198 (7)0.0015 (6)0.0041 (6)0.0017 (6)
C90.0181 (8)0.0167 (8)0.0152 (7)0.0005 (6)0.0030 (6)0.0030 (6)
C100.0132 (8)0.0133 (7)0.0174 (7)0.0008 (6)0.0014 (6)0.0005 (6)
C110.0155 (8)0.0164 (8)0.0143 (7)0.0026 (6)0.0018 (6)0.0027 (6)
C120.0189 (9)0.0188 (8)0.0167 (7)0.0021 (7)0.0042 (6)0.0029 (6)
C130.0175 (8)0.0151 (8)0.0211 (8)0.0008 (6)0.0050 (6)0.0002 (6)
C140.0110 (8)0.0150 (7)0.0194 (7)0.0019 (6)0.0029 (6)0.0011 (6)
C150.0125 (8)0.0159 (7)0.0160 (7)0.0015 (6)0.0017 (6)0.0015 (6)
C160.0161 (8)0.0184 (8)0.0174 (7)0.0002 (6)0.0016 (6)0.0020 (6)
C170.0201 (9)0.0249 (9)0.0159 (7)0.0007 (7)0.0006 (6)0.0002 (6)
C180.0189 (9)0.0251 (9)0.0196 (8)0.0016 (7)0.0025 (6)0.0061 (6)
C190.0162 (8)0.0167 (8)0.0234 (8)0.0006 (6)0.0015 (6)0.0042 (6)
C200.0173 (8)0.0193 (8)0.0147 (7)0.0020 (6)0.0021 (6)0.0014 (6)
C210.0214 (9)0.0174 (8)0.0177 (8)0.0024 (7)0.0008 (6)0.0014 (6)
C220.0157 (8)0.0165 (8)0.0175 (7)0.0002 (6)0.0015 (6)0.0030 (6)
C230.0136 (8)0.0162 (7)0.0150 (7)0.0014 (6)0.0013 (6)0.0018 (6)
C240.0145 (8)0.0145 (7)0.0164 (7)0.0005 (6)0.0022 (6)0.0011 (6)
C250.0148 (8)0.0171 (8)0.0142 (7)0.0027 (6)0.0030 (6)0.0013 (6)
C260.0131 (8)0.0175 (8)0.0155 (7)0.0007 (6)0.0003 (6)0.0030 (6)
C270.0152 (8)0.0144 (7)0.0207 (8)0.0012 (6)0.0028 (6)0.0002 (6)
C280.0175 (8)0.0171 (8)0.0155 (7)0.0003 (6)0.0022 (6)0.0012 (6)
C290.0137 (8)0.0139 (7)0.0174 (7)0.0007 (6)0.0022 (6)0.0013 (6)
C300.0142 (8)0.0166 (8)0.0154 (7)0.0022 (6)0.0020 (6)0.0006 (6)
C310.0204 (9)0.0193 (8)0.0152 (7)0.0017 (7)0.0046 (6)0.0046 (6)
C320.0167 (8)0.0155 (8)0.0205 (8)0.0009 (6)0.0061 (6)0.0021 (6)
C330.0127 (8)0.0161 (7)0.0178 (7)0.0011 (6)0.0026 (6)0.0013 (6)
C340.0132 (8)0.0162 (7)0.0156 (7)0.0021 (6)0.0023 (6)0.0009 (6)
C350.0157 (8)0.0182 (8)0.0186 (8)0.0020 (6)0.0021 (6)0.0028 (6)
C360.0236 (9)0.0249 (9)0.0158 (7)0.0036 (7)0.0012 (6)0.0018 (6)
C370.0209 (9)0.0256 (9)0.0187 (8)0.0019 (7)0.0013 (6)0.0034 (6)
C380.0163 (8)0.0183 (8)0.0220 (8)0.0007 (6)0.0014 (6)0.0021 (6)
C390.0186 (8)0.0180 (8)0.0142 (7)0.0018 (6)0.0000 (6)0.0017 (6)
C400.0210 (9)0.0182 (8)0.0179 (8)0.0035 (7)0.0033 (6)0.0015 (6)
C410.0156 (8)0.0165 (8)0.0169 (7)0.0001 (6)0.0020 (6)0.0001 (6)
C420.0140 (8)0.0156 (7)0.0144 (7)0.0027 (6)0.0014 (6)0.0008 (6)
C430.0140 (8)0.0152 (7)0.0173 (7)0.0003 (6)0.0018 (6)0.0022 (6)
C440.0144 (8)0.0178 (8)0.0140 (7)0.0015 (6)0.0008 (6)0.0038 (6)
C450.0141 (8)0.0175 (8)0.0155 (7)0.0010 (6)0.0031 (6)0.0024 (6)
C460.0155 (8)0.0147 (7)0.0200 (8)0.0004 (6)0.0006 (6)0.0012 (6)
C470.0180 (8)0.0172 (8)0.0150 (7)0.0006 (6)0.0000 (6)0.0032 (6)
C480.0144 (8)0.0135 (7)0.0167 (7)0.0007 (6)0.0008 (6)0.0014 (6)
C490.0136 (8)0.0173 (8)0.0151 (7)0.0024 (6)0.0010 (6)0.0019 (6)
C500.0175 (8)0.0175 (8)0.0166 (7)0.0021 (6)0.0013 (6)0.0023 (6)
C510.0142 (8)0.0152 (8)0.0230 (8)0.0015 (6)0.0008 (6)0.0008 (6)
C520.0117 (8)0.0163 (8)0.0185 (7)0.0019 (6)0.0008 (6)0.0028 (6)
C530.0107 (8)0.0172 (8)0.0161 (7)0.0014 (6)0.0013 (6)0.0014 (6)
C540.0165 (8)0.0198 (8)0.0182 (8)0.0005 (6)0.0006 (6)0.0002 (6)
C550.0203 (9)0.0295 (9)0.0140 (7)0.0033 (7)0.0015 (6)0.0007 (6)
C560.0220 (9)0.0278 (9)0.0195 (8)0.0033 (7)0.0050 (7)0.0087 (7)
C570.0158 (8)0.0185 (8)0.0241 (8)0.0009 (6)0.0032 (6)0.0069 (6)
C580.0179 (8)0.0193 (8)0.0139 (7)0.0020 (6)0.0005 (6)0.0010 (6)
C590.0212 (9)0.0182 (8)0.0171 (7)0.0031 (7)0.0024 (6)0.0017 (6)
C600.0162 (8)0.0174 (8)0.0170 (7)0.0002 (6)0.0014 (6)0.0024 (6)
C610.0130 (8)0.0172 (8)0.0160 (7)0.0014 (6)0.0016 (6)0.0022 (6)
C620.0140 (8)0.0152 (7)0.0182 (7)0.0006 (6)0.0012 (6)0.0016 (6)
C630.0146 (8)0.0183 (8)0.0142 (7)0.0019 (6)0.0010 (6)0.0011 (6)
C640.0141 (8)0.0188 (8)0.0151 (7)0.0013 (6)0.0031 (6)0.0054 (6)
C650.0159 (8)0.0145 (7)0.0200 (8)0.0015 (6)0.0007 (6)0.0018 (6)
C660.0175 (8)0.0164 (8)0.0153 (7)0.0003 (6)0.0001 (6)0.0006 (6)
C670.0141 (8)0.0139 (7)0.0167 (7)0.0012 (6)0.0006 (6)0.0017 (6)
C680.0154 (8)0.0165 (8)0.0146 (7)0.0034 (6)0.0011 (6)0.0008 (6)
C690.0182 (8)0.0185 (8)0.0159 (7)0.0021 (6)0.0016 (6)0.0042 (6)
C700.0152 (8)0.0152 (8)0.0208 (8)0.0016 (6)0.0006 (6)0.0029 (6)
C710.0115 (8)0.0165 (8)0.0182 (7)0.0020 (6)0.0005 (6)0.0018 (6)
C720.0109 (8)0.0160 (7)0.0157 (7)0.0022 (6)0.0007 (6)0.0021 (6)
C730.0170 (8)0.0183 (8)0.0173 (7)0.0001 (6)0.0007 (6)0.0030 (6)
C740.0240 (9)0.0232 (8)0.0150 (7)0.0023 (7)0.0012 (6)0.0025 (6)
C750.0207 (9)0.0238 (9)0.0194 (8)0.0020 (7)0.0052 (6)0.0036 (6)
C760.0161 (8)0.0165 (8)0.0226 (8)0.0003 (6)0.0024 (6)0.0013 (6)
Geometric parameters (Å, º) top
Cl1—C61.7246 (15)C35—H350.9500
Cl2—C71.7275 (16)C36—C371.409 (2)
Cl3—C251.7244 (15)C36—H360.9500
Cl4—C261.7258 (15)C37—C381.369 (2)
Cl5—C441.7239 (15)C37—H370.9500
Cl6—C451.7255 (16)C38—H380.9500
Cl7—C631.7229 (16)C39—C401.484 (2)
Cl8—C641.7286 (15)C39—C491.491 (2)
O1—C11.2212 (19)C40—C411.332 (2)
O2—C201.2209 (19)C40—H400.9500
O3—C391.2241 (19)C41—C421.468 (2)
O4—C581.2193 (19)C41—H410.9500
C1—C21.482 (2)C42—C471.396 (2)
C1—C111.495 (2)C42—C431.405 (2)
C2—C31.337 (2)C43—C441.386 (2)
C2—H20.9500C43—H430.9500
C3—C41.467 (2)C44—C451.390 (2)
C3—H30.9500C45—C461.392 (2)
C4—C91.397 (2)C46—C471.384 (2)
C4—C51.400 (2)C46—H460.9500
C5—C61.387 (2)C47—H470.9500
C5—H50.9500C48—C491.380 (2)
C6—C71.389 (2)C48—C531.414 (2)
C7—C81.391 (2)C48—H480.9500
C8—C91.384 (2)C49—C501.417 (2)
C8—H80.9500C50—C511.368 (2)
C9—H90.9500C50—H500.9500
C10—C111.379 (2)C51—C521.415 (2)
C10—C151.414 (2)C51—H510.9500
C10—H100.9500C52—C571.421 (2)
C11—C121.417 (2)C52—C531.424 (2)
C12—C131.370 (2)C53—C541.419 (2)
C12—H120.9500C54—C551.369 (2)
C13—C141.418 (2)C54—H540.9500
C13—H130.9500C55—C561.409 (2)
C14—C191.420 (2)C55—H550.9500
C14—C151.424 (2)C56—C571.365 (2)
C15—C161.420 (2)C56—H560.9500
C16—C171.368 (2)C57—H570.9500
C16—H160.9500C58—C591.480 (2)
C17—C181.411 (2)C58—C681.497 (2)
C17—H170.9500C59—C601.336 (2)
C18—C191.366 (2)C59—H590.9500
C18—H180.9500C60—C611.468 (2)
C19—H190.9500C60—H600.9500
C20—C211.482 (2)C61—C661.398 (2)
C20—C301.492 (2)C61—C621.399 (2)
C21—C221.335 (2)C62—C631.389 (2)
C21—H210.9500C62—H620.9500
C22—C231.468 (2)C63—C641.386 (2)
C22—H220.9500C64—C651.393 (2)
C23—C281.400 (2)C65—C661.384 (2)
C23—C241.400 (2)C65—H650.9500
C24—C251.390 (2)C66—H660.9500
C24—H240.9500C67—C681.381 (2)
C25—C261.386 (2)C67—C721.415 (2)
C26—C271.395 (2)C67—H670.9500
C27—C281.384 (2)C68—C691.413 (2)
C27—H270.9500C69—C701.370 (2)
C28—H280.9500C69—H690.9500
C29—C301.383 (2)C70—C711.419 (2)
C29—C341.413 (2)C70—H700.9500
C29—H290.9500C71—C721.420 (2)
C30—C311.417 (2)C71—C761.421 (2)
C31—C321.368 (2)C72—C731.422 (2)
C31—H310.9500C73—C741.373 (2)
C32—C331.420 (2)C73—H730.9500
C32—H320.9500C74—C751.411 (2)
C33—C381.418 (2)C74—H740.9500
C33—C341.422 (2)C75—C761.368 (2)
C34—C351.421 (2)C75—H750.9500
C35—C361.369 (2)C76—H760.9500
O1—C1—C2121.90 (14)O3—C39—C40121.64 (14)
O1—C1—C11120.52 (14)O3—C39—C49120.78 (14)
C2—C1—C11117.57 (13)C40—C39—C49117.58 (13)
C3—C2—C1120.43 (15)C41—C40—C39120.45 (15)
C3—C2—H2119.8C41—C40—H40119.8
C1—C2—H2119.8C39—C40—H40119.8
C2—C3—C4125.77 (15)C40—C41—C42125.94 (15)
C2—C3—H3117.1C40—C41—H41117.0
C4—C3—H3117.1C42—C41—H41117.0
C9—C4—C5118.88 (14)C47—C42—C43118.94 (14)
C9—C4—C3122.70 (14)C47—C42—C41122.89 (13)
C5—C4—C3118.42 (14)C43—C42—C41118.16 (14)
C6—C5—C4120.36 (14)C44—C43—C42120.05 (14)
C6—C5—H5119.8C44—C43—H43120.0
C4—C5—H5119.8C42—C43—H43120.0
C5—C6—C7120.10 (14)C43—C44—C45120.46 (13)
C5—C6—Cl1119.34 (12)C43—C44—Cl5119.29 (12)
C7—C6—Cl1120.56 (12)C45—C44—Cl5120.24 (12)
C6—C7—C8120.04 (14)C44—C45—C46119.78 (14)
C6—C7—Cl2120.74 (12)C44—C45—Cl6120.85 (12)
C8—C7—Cl2119.21 (12)C46—C45—Cl6119.37 (12)
C9—C8—C7119.89 (15)C47—C46—C45119.99 (15)
C9—C8—H8120.1C47—C46—H46120.0
C7—C8—H8120.1C45—C46—H46120.0
C8—C9—C4120.72 (14)C46—C47—C42120.77 (14)
C8—C9—H9119.6C46—C47—H47119.6
C4—C9—H9119.6C42—C47—H47119.6
C11—C10—C15120.81 (14)C49—C48—C53120.84 (14)
C11—C10—H10119.6C49—C48—H48119.6
C15—C10—H10119.6C53—C48—H48119.6
C10—C11—C12119.97 (14)C48—C49—C50119.95 (14)
C10—C11—C1118.11 (14)C48—C49—C39118.11 (14)
C12—C11—C1121.91 (14)C50—C49—C39121.93 (14)
C13—C12—C11120.29 (14)C51—C50—C49120.23 (14)
C13—C12—H12119.9C51—C50—H50119.9
C11—C12—H12119.9C49—C50—H50119.9
C12—C13—C14120.88 (15)C50—C51—C52121.00 (15)
C12—C13—H13119.6C50—C51—H51119.5
C14—C13—H13119.6C52—C51—H51119.5
C13—C14—C19122.14 (14)C51—C52—C57122.25 (15)
C13—C14—C15118.93 (14)C51—C52—C53119.02 (14)
C19—C14—C15118.93 (14)C57—C52—C53118.72 (14)
C10—C15—C16121.85 (14)C48—C53—C54121.89 (14)
C10—C15—C14119.05 (14)C48—C53—C52118.90 (14)
C16—C15—C14119.10 (14)C54—C53—C52119.21 (14)
C17—C16—C15120.36 (15)C55—C54—C53120.37 (15)
C17—C16—H16119.8C55—C54—H54119.8
C15—C16—H16119.8C53—C54—H54119.8
C16—C17—C18120.52 (15)C54—C55—C56120.47 (15)
C16—C17—H17119.7C54—C55—H55119.8
C18—C17—H17119.7C56—C55—H55119.8
C19—C18—C17120.64 (14)C57—C56—C55120.64 (15)
C19—C18—H18119.7C57—C56—H56119.7
C17—C18—H18119.7C55—C56—H56119.7
C18—C19—C14120.44 (15)C56—C57—C52120.57 (15)
C18—C19—H19119.8C56—C57—H57119.7
C14—C19—H19119.8C52—C57—H57119.7
O2—C20—C21121.80 (14)O4—C58—C59121.78 (15)
O2—C20—C30120.90 (14)O4—C58—C68120.78 (14)
C21—C20—C30117.30 (14)C59—C58—C68117.44 (14)
C22—C21—C20120.46 (15)C60—C59—C58120.44 (15)
C22—C21—H21119.8C60—C59—H59119.8
C20—C21—H21119.8C58—C59—H59119.8
C21—C22—C23125.74 (15)C59—C60—C61126.00 (15)
C21—C22—H22117.1C59—C60—H60117.0
C23—C22—H22117.1C61—C60—H60117.0
C28—C23—C24118.84 (13)C66—C61—C62118.95 (14)
C28—C23—C22122.59 (14)C66—C61—C60122.73 (14)
C24—C23—C22118.57 (14)C62—C61—C60118.31 (14)
C25—C24—C23120.42 (14)C63—C62—C61120.37 (14)
C25—C24—H24119.8C63—C62—H62119.8
C23—C24—H24119.8C61—C62—H62119.8
C26—C25—C24120.08 (14)C64—C63—C62120.05 (14)
C26—C25—Cl3120.54 (12)C64—C63—Cl7120.53 (12)
C24—C25—Cl3119.38 (12)C62—C63—Cl7119.41 (12)
C25—C26—C27120.03 (14)C63—C64—C65120.10 (14)
C25—C26—Cl4120.98 (12)C63—C64—Cl8120.92 (12)
C27—C26—Cl4118.99 (12)C65—C64—Cl8118.98 (12)
C28—C27—C26119.96 (14)C66—C65—C64119.95 (15)
C28—C27—H27120.0C66—C65—H65120.0
C26—C27—H27120.0C64—C65—H65120.0
C27—C28—C23120.66 (14)C65—C66—C61120.57 (14)
C27—C28—H28119.7C65—C66—H66119.7
C23—C28—H28119.7C61—C66—H66119.7
C30—C29—C34120.75 (14)C68—C67—C72120.57 (14)
C30—C29—H29119.6C68—C67—H67119.7
C34—C29—H29119.6C72—C67—H67119.7
C29—C30—C31119.72 (14)C67—C68—C69120.09 (14)
C29—C30—C20118.11 (14)C67—C68—C58117.86 (14)
C31—C30—C20122.17 (13)C69—C68—C58122.05 (13)
C32—C31—C30120.61 (14)C70—C69—C68120.37 (14)
C32—C31—H31119.7C70—C69—H69119.8
C30—C31—H31119.7C68—C69—H69119.8
C31—C32—C33120.68 (14)C69—C70—C71120.73 (15)
C31—C32—H32119.7C69—C70—H70119.6
C33—C32—H32119.7C71—C70—H70119.6
C38—C33—C32121.89 (15)C70—C71—C72119.03 (14)
C38—C33—C34119.14 (14)C70—C71—C76121.91 (14)
C32—C33—C34118.96 (14)C72—C71—C76119.06 (14)
C29—C34—C35121.81 (14)C67—C72—C71119.14 (13)
C29—C34—C33119.22 (14)C67—C72—C73121.65 (14)
C35—C34—C33118.97 (14)C71—C72—C73119.21 (14)
C36—C35—C34120.39 (15)C74—C73—C72120.26 (15)
C36—C35—H35119.8C74—C73—H73119.9
C34—C35—H35119.8C72—C73—H73119.9
C35—C36—C37120.54 (15)C73—C74—C75120.41 (15)
C35—C36—H36119.7C73—C74—H74119.8
C37—C36—H36119.7C75—C74—H74119.8
C38—C37—C36120.57 (15)C76—C75—C74120.67 (15)
C38—C37—H37119.7C76—C75—H75119.7
C36—C37—H37119.7C74—C75—H75119.7
C37—C38—C33120.38 (15)C75—C76—C71120.37 (15)
C37—C38—H38119.8C75—C76—H76119.8
C33—C38—H38119.8C71—C76—H76119.8
O1—C1—C2—C316.4 (3)O3—C39—C40—C4114.9 (3)
C11—C1—C2—C3164.66 (15)C49—C39—C40—C41165.71 (15)
C1—C2—C3—C4177.23 (15)C39—C40—C41—C42177.56 (15)
C2—C3—C4—C911.3 (3)C40—C41—C42—C4711.3 (3)
C2—C3—C4—C5168.55 (16)C40—C41—C42—C43168.90 (16)
C9—C4—C5—C60.1 (2)C47—C42—C43—C440.4 (2)
C3—C4—C5—C6179.73 (14)C41—C42—C43—C44179.80 (14)
C4—C5—C6—C70.3 (2)C42—C43—C44—C450.3 (2)
C4—C5—C6—Cl1179.48 (12)C42—C43—C44—Cl5179.52 (12)
C5—C6—C7—C80.2 (2)C43—C44—C45—C460.1 (2)
Cl1—C6—C7—C8179.99 (12)Cl5—C44—C45—C46179.02 (12)
C5—C6—C7—Cl2178.97 (12)C43—C44—C45—Cl6179.46 (12)
Cl1—C6—C7—Cl21.26 (19)Cl5—C44—C45—Cl60.3 (2)
C6—C7—C8—C90.9 (2)C44—C45—C46—C470.6 (2)
Cl2—C7—C8—C9179.68 (12)Cl6—C45—C46—C47179.97 (12)
C7—C8—C9—C41.1 (2)C45—C46—C47—C420.6 (2)
C5—C4—C9—C80.6 (2)C43—C42—C47—C460.1 (2)
C3—C4—C9—C8179.58 (15)C41—C42—C47—C46179.70 (15)
C15—C10—C11—C120.5 (2)C53—C48—C49—C500.5 (2)
C15—C10—C11—C1179.89 (14)C53—C48—C49—C39179.83 (14)
O1—C1—C11—C1025.3 (2)O3—C39—C49—C4825.8 (2)
C2—C1—C11—C10153.71 (15)C40—C39—C49—C48153.58 (15)
O1—C1—C11—C12154.15 (16)O3—C39—C49—C50153.49 (16)
C2—C1—C11—C1226.9 (2)C40—C39—C49—C5027.1 (2)
C10—C11—C12—C132.0 (2)C48—C49—C50—C511.7 (2)
C1—C11—C12—C13177.42 (15)C39—C49—C50—C51177.61 (15)
C11—C12—C13—C142.7 (2)C49—C50—C51—C522.3 (2)
C12—C13—C14—C19178.56 (15)C50—C51—C52—C57178.52 (15)
C12—C13—C14—C150.9 (2)C50—C51—C52—C530.8 (2)
C11—C10—C15—C16177.72 (15)C49—C48—C53—C54177.73 (14)
C11—C10—C15—C142.2 (2)C49—C48—C53—C522.0 (2)
C13—C14—C15—C101.5 (2)C51—C52—C53—C481.4 (2)
C19—C14—C15—C10179.02 (14)C57—C52—C53—C48179.30 (14)
C13—C14—C15—C16178.41 (14)C51—C52—C53—C54178.39 (14)
C19—C14—C15—C161.1 (2)C57—C52—C53—C540.9 (2)
C10—C15—C16—C17179.55 (15)C48—C53—C54—C55179.85 (15)
C14—C15—C16—C170.6 (2)C52—C53—C54—C550.1 (2)
C15—C16—C17—C180.0 (3)C53—C54—C55—C560.6 (2)
C16—C17—C18—C190.0 (3)C54—C55—C56—C570.4 (3)
C17—C18—C19—C140.6 (3)C55—C56—C57—C520.5 (3)
C13—C14—C19—C18178.40 (15)C51—C52—C57—C56178.14 (15)
C15—C14—C19—C181.1 (2)C53—C52—C57—C561.2 (2)
O2—C20—C21—C2215.5 (3)O4—C58—C59—C6015.8 (3)
C30—C20—C21—C22165.11 (15)C68—C58—C59—C60164.81 (15)
C20—C21—C22—C23177.45 (15)C58—C59—C60—C61177.62 (15)
C21—C22—C23—C2810.3 (3)C59—C60—C61—C6611.6 (3)
C21—C22—C23—C24169.81 (16)C59—C60—C61—C62168.95 (16)
C28—C23—C24—C250.3 (2)C66—C61—C62—C630.6 (2)
C22—C23—C24—C25179.82 (14)C60—C61—C62—C63179.96 (14)
C23—C24—C25—C260.1 (2)C61—C62—C63—C640.8 (2)
C23—C24—C25—Cl3179.94 (12)C61—C62—C63—Cl7179.76 (12)
C24—C25—C26—C270.7 (2)C62—C63—C64—C650.4 (2)
Cl3—C25—C26—C27179.46 (12)Cl7—C63—C64—C65179.36 (12)
C24—C25—C26—Cl4179.92 (12)C62—C63—C64—Cl8178.92 (12)
Cl3—C25—C26—Cl40.3 (2)Cl7—C63—C64—Cl80.02 (19)
C25—C26—C27—C280.9 (2)C63—C64—C65—C660.2 (2)
Cl4—C26—C27—C28179.85 (12)Cl8—C64—C65—C66179.51 (12)
C26—C27—C28—C230.5 (2)C64—C65—C66—C610.4 (2)
C24—C23—C28—C270.0 (2)C62—C61—C66—C650.0 (2)
C22—C23—C28—C27179.97 (15)C60—C61—C66—C65179.44 (15)
C34—C29—C30—C310.2 (2)C72—C67—C68—C690.5 (2)
C34—C29—C30—C20179.82 (14)C72—C67—C68—C58179.99 (14)
O2—C20—C30—C2925.9 (2)O4—C58—C68—C6725.6 (2)
C21—C20—C30—C29153.50 (15)C59—C58—C68—C67153.76 (15)
O2—C20—C30—C31153.74 (16)O4—C58—C68—C69153.83 (16)
C21—C20—C30—C3126.9 (2)C59—C58—C68—C6926.8 (2)
C29—C30—C31—C322.0 (2)C67—C68—C69—C701.9 (2)
C20—C30—C31—C32177.58 (15)C58—C68—C69—C70177.53 (15)
C30—C31—C32—C332.7 (2)C68—C69—C70—C712.6 (2)
C31—C32—C33—C38178.73 (15)C69—C70—C71—C720.9 (2)
C31—C32—C33—C341.2 (2)C69—C70—C71—C76178.78 (15)
C30—C29—C34—C35177.97 (15)C68—C67—C72—C712.3 (2)
C30—C29—C34—C331.7 (2)C68—C67—C72—C73178.02 (15)
C38—C33—C34—C29179.09 (14)C70—C71—C72—C671.6 (2)
C32—C33—C34—C291.0 (2)C76—C71—C72—C67178.80 (14)
C38—C33—C34—C351.3 (2)C70—C71—C72—C73178.71 (14)
C32—C33—C34—C35178.64 (14)C76—C71—C72—C730.9 (2)
C29—C34—C35—C36179.91 (15)C67—C72—C73—C74179.76 (15)
C33—C34—C35—C360.4 (2)C71—C72—C73—C740.0 (2)
C34—C35—C36—C370.3 (3)C72—C73—C74—C750.6 (3)
C35—C36—C37—C380.3 (3)C73—C74—C75—C760.1 (3)
C36—C37—C38—C330.5 (3)C74—C75—C76—C710.9 (3)
C32—C33—C38—C37178.59 (16)C70—C71—C76—C75178.21 (15)
C34—C33—C38—C371.3 (2)C72—C71—C76—C751.4 (2)

Experimental details

Crystal data
Chemical formulaC19H12Cl2O
Mr327.19
Crystal system, space groupTriclinic, P1
Temperature (K)113
a, b, c (Å)7.5273 (10), 11.5212 (14), 33.301 (4)
α, β, γ (°)92.338 (7), 96.469 (7), 90.125 (6)
V3)2867.1 (6)
Z8
Radiation typeMo Kα
µ (mm1)0.45
Crystal size (mm)0.36 × 0.34 × 0.28
Data collection
DiffractometerRigaku Saturn CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.855, 0.884
No. of measured, independent and
observed [I > 2σ(I)] reflections
26590, 13067, 10135
Rint0.023
(sin θ/λ)max1)0.659
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.106, 1.07
No. of reflections13067
No. of parameters793
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.44

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2004).

 

Acknowledgements

The authors thank Dr Haibin Song of Nankai University for helpful discussions and the Science Foundation of Guangxi University for financial support.

References

First citationLu, Z.-K., Huang, P.-M. & Yu, J.-F. (2006). Acta Cryst. E62, o5753–o5754.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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