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The crystal structure of the title compound, [CuCl2(C14H12N2)(H2O)], previously reported by Preston & Kennard [J. Chem. Soc. A (1969). pp. 2955–2958], has been redetermined. The recognition of an inversion twin allowed a much better refinement.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802022249/su6007sup1.cif
Contains datablocks pl205, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802022249/su6007Isup2.hkl
Contains datablock I

CCDC reference: 202971

Key indicators

  • Single-crystal X-ray study
  • T = 180 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.017
  • wR factor = 0.046
  • Data-to-parameter ratio = 11.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
STRVAL_01 From the CIF: _refine_ls_abs_structure_Flack 0.538 From the CIF: _refine_ls_abs_structure_Flack_su 0.008 Alert C Flack test results are ambiguous. General Notes
ABSTM_02 When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 1.210 Tmax scaled 0.688 Tmin scaled 0.618 REFLT_03 From the CIF: _diffrn_reflns_theta_max 26.07 From the CIF: _reflns_number_total 2499 Count of symmetry unique reflns 1548 Completeness (_total/calc) 161.43% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 951 Fraction of Friedel pairs measured 0.614 Are heavy atom types Z>Si present yes Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: IPDS Manual (Stoe & Cie, 1996); cell refinement: IPDS Manual; data reduction: X-RED (Stoe & Cie, 1996); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Version 1.63.02; Farrugia, 1999).

Aquadichloro(2,9-dimethyl-1,10-phenanthroline-κ2N,N')copper(II) top
Crystal data top
[CuCl2(C14H12N2)(H2O)]F(000) = 366
Mr = 360.71Dx = 1.652 Mg m3
Dm = 1.63 (2) Mg m3
Dm measured by flotation in CCl4/C2H4Br2
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 5681 reflections
a = 9.462 (1) Åθ = 2.2–26.1°
b = 8.093 (1) ŵ = 1.87 mm1
c = 9.823 (1) ÅT = 180 K
β = 105.38 (1)°Parallelepiped, green
V = 725.3 (1) Å30.30 × 0.25 × 0.20 mm
Z = 2
Data collection top
Stoe IPDS
diffractometer
2499 independent reflections
Radiation source: fine-focus sealed tube2425 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
φ scansθmax = 26.1°, θmin = 2.2°
Absorption correction: empirical (using intensity measurements)
multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995)
h = 1010
Tmin = 0.511, Tmax = 0.569k = 99
5663 measured reflectionsl = 1212
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.017All H-atom parameters refined
wR(F2) = 0.046 w = 1/[σ2(Fo2) + (0.0354P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2499 reflectionsΔρmax = 0.27 e Å3
225 parametersΔρmin = 0.21 e Å3
1 restraintAbsolute structure: Flack (1983), 0000 Friedel pairs [Please provide]
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.538 (8)
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
Cu10.15881 (2)0.220674 (18)0.19145 (2)0.01179 (7)
Cl10.05817 (6)0.02625 (6)0.23519 (5)0.01767 (12)
Cl20.18241 (6)0.50374 (6)0.19125 (5)0.01946 (12)
OW10.00771 (18)0.2446 (2)0.02469 (15)0.0195 (3)
N10.31411 (17)0.2231 (2)0.37350 (15)0.0128 (3)
C20.2898 (3)0.2593 (2)0.4977 (2)0.0158 (4)
C30.4097 (3)0.2829 (3)0.6175 (2)0.0189 (5)
C40.5498 (3)0.2745 (3)0.6073 (2)0.0195 (5)
C50.7203 (2)0.2218 (3)0.4567 (2)0.0235 (4)
C60.7400 (3)0.1813 (3)0.3303 (3)0.0234 (5)
C70.6322 (3)0.1035 (3)0.0778 (3)0.0237 (5)
C80.5093 (3)0.0765 (3)0.0298 (3)0.0220 (5)
C90.3682 (3)0.0996 (3)0.0091 (2)0.0174 (4)
N100.3519 (2)0.1454 (2)0.11619 (18)0.0138 (4)
C110.4741 (3)0.1697 (2)0.2252 (2)0.0145 (4)
C120.6164 (3)0.1528 (3)0.2105 (2)0.0181 (5)
C130.5768 (2)0.2363 (3)0.47618 (19)0.0176 (4)
C140.4533 (2)0.2103 (3)0.36087 (18)0.0136 (4)
C150.1362 (3)0.2746 (3)0.5066 (2)0.0222 (5)
C160.2336 (3)0.0715 (3)0.1262 (2)0.0244 (5)
HW10.013 (4)0.320 (4)0.024 (4)0.037 (2)*
HW20.037 (4)0.171 (4)0.020 (4)0.037 (2)*
H30.388 (4)0.311 (4)0.709 (3)0.037 (2)*
H40.629 (4)0.291 (4)0.686 (3)0.037 (2)*
H50.784 (4)0.249 (4)0.522 (3)0.037 (2)*
H60.824 (4)0.173 (4)0.318 (3)0.037 (2)*
H70.730 (5)0.094 (4)0.068 (4)0.037 (2)*
H80.514 (4)0.037 (4)0.117 (4)0.037 (2)*
H1510.132 (4)0.314 (4)0.592 (3)0.037 (2)*
H1520.095 (4)0.180 (5)0.497 (3)0.037 (2)*
H1530.091 (4)0.344 (4)0.433 (3)0.037 (2)*
H1610.163 (4)0.012 (4)0.105 (3)0.037 (2)*
H1620.253 (4)0.027 (4)0.212 (3)0.037 (2)*
H1630.185 (4)0.175 (4)0.148 (3)0.037 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.01057 (13)0.01366 (12)0.00996 (11)0.00022 (10)0.00064 (7)0.00025 (9)
Cl10.0217 (3)0.0154 (2)0.0154 (2)0.00353 (19)0.00407 (18)0.00025 (18)
Cl20.0223 (3)0.0131 (2)0.0182 (2)0.00076 (19)0.00300 (19)0.00130 (17)
OW10.0217 (9)0.0156 (8)0.0159 (7)0.0035 (7)0.0041 (6)0.0015 (6)
N10.0128 (9)0.0128 (7)0.0124 (7)0.0003 (8)0.0025 (5)0.0011 (7)
C20.0192 (13)0.0136 (10)0.0145 (9)0.0006 (7)0.0046 (8)0.0014 (7)
C30.0221 (15)0.0192 (10)0.0143 (10)0.0018 (9)0.0031 (9)0.0006 (8)
C40.0189 (14)0.0192 (10)0.0156 (10)0.0021 (8)0.0037 (8)0.0013 (7)
C50.0110 (11)0.0289 (11)0.0255 (10)0.0010 (11)0.0041 (7)0.0015 (11)
C60.0110 (13)0.0279 (13)0.0308 (12)0.0031 (8)0.0046 (9)0.0026 (9)
C70.0197 (15)0.0286 (11)0.0267 (12)0.0040 (9)0.0131 (10)0.0013 (9)
C80.0234 (15)0.0258 (13)0.0208 (12)0.0028 (9)0.0128 (9)0.0007 (8)
C90.0192 (13)0.0183 (9)0.0156 (10)0.0007 (8)0.0064 (8)0.0005 (8)
N100.0113 (11)0.0158 (8)0.0151 (8)0.0006 (6)0.0047 (7)0.0010 (6)
C110.0136 (12)0.0124 (9)0.0168 (9)0.0005 (7)0.0028 (8)0.0009 (7)
C120.0134 (13)0.0208 (10)0.0210 (11)0.0011 (8)0.0062 (8)0.0021 (8)
C130.0172 (12)0.0147 (9)0.0188 (9)0.0015 (9)0.0010 (7)0.0025 (9)
C140.0125 (10)0.0113 (8)0.0162 (8)0.0009 (9)0.0024 (7)0.0018 (8)
C150.0168 (14)0.0328 (13)0.0173 (10)0.0003 (9)0.0051 (9)0.0048 (9)
C160.0236 (16)0.0352 (14)0.0147 (11)0.0021 (10)0.0055 (9)0.0055 (8)
Geometric parameters (Å, º) top
Cu1—OW11.9582 (15)C5—C131.425 (3)
Cu1—N11.9911 (15)C6—C121.441 (3)
Cu1—N102.230 (2)C7—C81.365 (4)
Cu1—Cl22.3017 (5)C7—C121.409 (3)
Cu1—Cl12.3026 (6)C8—C91.415 (4)
N1—C21.333 (3)C9—N101.332 (3)
N1—C141.359 (3)C9—C161.490 (4)
C2—C31.415 (3)N10—C111.366 (3)
C2—C151.484 (4)C11—C121.398 (4)
C3—C41.357 (4)C11—C141.436 (3)
C4—C131.412 (3)C13—C141.411 (3)
C5—C61.344 (3)
OW1—Cu1—N1171.44 (7)C8—C7—C12118.9 (2)
OW1—Cu1—N10107.34 (7)C7—C8—C9120.7 (2)
N1—Cu1—N1079.98 (7)N10—C9—C8120.9 (2)
OW1—Cu1—Cl287.57 (5)N10—C9—C16118.1 (2)
N1—Cu1—Cl286.68 (6)C8—C9—C16121.0 (2)
N10—Cu1—Cl2100.57 (5)C9—N10—C11118.9 (2)
OW1—Cu1—Cl187.77 (6)C9—N10—Cu1133.46 (16)
N1—Cu1—Cl194.84 (5)C11—N10—Cu1107.36 (14)
N10—Cu1—Cl1103.92 (5)N10—C11—C12122.9 (2)
Cl2—Cu1—Cl1155.36 (2)N10—C11—C14117.7 (2)
C2—N1—C14120.47 (17)C12—C11—C14119.40 (19)
C2—N1—Cu1123.98 (15)C11—C12—C7117.7 (2)
C14—N1—Cu1114.81 (11)C11—C12—C6119.7 (2)
N1—C2—C3119.7 (2)C7—C12—C6122.6 (3)
N1—C2—C15118.81 (19)C14—C13—C4117.0 (2)
C3—C2—C15121.45 (19)C14—C13—C5119.70 (18)
C4—C3—C2121.0 (2)C4—C13—C5123.34 (19)
C3—C4—C13119.7 (2)N1—C14—C13122.11 (17)
C6—C5—C13121.0 (2)N1—C14—C11118.49 (17)
C5—C6—C12120.8 (3)C13—C14—C11119.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
OW1—HW1···Cl1i0.77 (4)2.36 (4)3.0882 (17)159 (3)
OW1—HW2···Cl2ii0.75 (4)2.31 (4)3.0286 (17)162 (3)
Symmetry codes: (i) x, y+1/2, z; (ii) x, y1/2, z.
 

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