Aqua­di­chloro(2,9-di­methyl-1,10-phenanthroline-κ²N,N′)copper(II)

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.

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


 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

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Computing details

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)

Crystal data

[CuCl2(C14H12N2)(H2O)]	F(000) = 366
Mr = 360.71	Dx = 1.652 Mg m^−3 Dm = 1.63 (2) Mg m^−3 Dm measured by flotation in CCl4/C2H4Br2
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5681 reflections
a = 9.462 (1) Å	θ = 2.2–26.1°
b = 8.093 (1) Å	µ = 1.87 mm^−1
c = 9.823 (1) Å	T = 180 K
β = 105.38 (1)°	Parallelepiped, green
V = 725.3 (1) Å^3	0.30 × 0.25 × 0.20 mm
Z = 2

Data collection

Stoe IPDS diffractometer	2499 independent reflections
Radiation source: fine-focus sealed tube	2425 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ scans	θmax = 26.1°, θmin = 2.2°
Absorption correction: empirical (using intensity measurements) multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995)	h = −10→10
Tmin = 0.511, Tmax = 0.569	k = −9→9
5663 measured reflections	l = −12→12

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.017	All H-atom parameters refined
wR(F^2) = 0.046	w = 1/[σ^2(Fo^2) + (0.0354P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2499 reflections	Δρmax = 0.27 e Å^−3
225 parameters	Δρmin = −0.21 e Å^−3
1 restraint	Absolute structure: Flack (1983), 0000 Friedel pairs [Please provide]
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.538 (8)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.15881 (2)	0.220674 (18)	0.19145 (2)	0.01179 (7)
Cl1	0.05817 (6)	−0.02625 (6)	0.23519 (5)	0.01767 (12)
Cl2	0.18241 (6)	0.50374 (6)	0.19125 (5)	0.01946 (12)
OW1	−0.00771 (18)	0.2446 (2)	0.02469 (15)	0.0195 (3)
N1	0.31411 (17)	0.2231 (2)	0.37350 (15)	0.0128 (3)
C2	0.2898 (3)	0.2593 (2)	0.4977 (2)	0.0158 (4)
C3	0.4097 (3)	0.2829 (3)	0.6175 (2)	0.0189 (5)
C4	0.5498 (3)	0.2745 (3)	0.6073 (2)	0.0195 (5)
C5	0.7203 (2)	0.2218 (3)	0.4567 (2)	0.0235 (4)
C6	0.7400 (3)	0.1813 (3)	0.3303 (3)	0.0234 (5)
C7	0.6322 (3)	0.1035 (3)	0.0778 (3)	0.0237 (5)
C8	0.5093 (3)	0.0765 (3)	−0.0298 (3)	0.0220 (5)
C9	0.3682 (3)	0.0996 (3)	−0.0091 (2)	0.0174 (4)
N10	0.3519 (2)	0.1454 (2)	0.11619 (18)	0.0138 (4)
C11	0.4741 (3)	0.1697 (2)	0.2252 (2)	0.0145 (4)
C12	0.6164 (3)	0.1528 (3)	0.2105 (2)	0.0181 (5)
C13	0.5768 (2)	0.2363 (3)	0.47618 (19)	0.0176 (4)
C14	0.4533 (2)	0.2103 (3)	0.36087 (18)	0.0136 (4)
C15	0.1362 (3)	0.2746 (3)	0.5066 (2)	0.0222 (5)
C16	0.2336 (3)	0.0715 (3)	−0.1262 (2)	0.0244 (5)
HW1	−0.013 (4)	0.320 (4)	−0.024 (4)	0.037 (2)*
HW2	−0.037 (4)	0.171 (4)	−0.020 (4)	0.037 (2)*
H3	0.388 (4)	0.311 (4)	0.709 (3)	0.037 (2)*
H4	0.629 (4)	0.291 (4)	0.686 (3)	0.037 (2)*
H5	0.784 (4)	0.249 (4)	0.522 (3)	0.037 (2)*
H6	0.824 (4)	0.173 (4)	0.318 (3)	0.037 (2)*
H7	0.730 (5)	0.094 (4)	0.068 (4)	0.037 (2)*
H8	0.514 (4)	0.037 (4)	−0.117 (4)	0.037 (2)*
H151	0.132 (4)	0.314 (4)	0.592 (3)	0.037 (2)*
H152	0.095 (4)	0.180 (5)	0.497 (3)	0.037 (2)*
H153	0.091 (4)	0.344 (4)	0.433 (3)	0.037 (2)*
H161	0.163 (4)	−0.012 (4)	−0.105 (3)	0.037 (2)*
H162	0.253 (4)	0.027 (4)	−0.212 (3)	0.037 (2)*
H163	0.185 (4)	0.175 (4)	−0.148 (3)	0.037 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.01057 (13)	0.01366 (12)	0.00996 (11)	0.00022 (10)	0.00064 (7)	0.00025 (9)
Cl1	0.0217 (3)	0.0154 (2)	0.0154 (2)	−0.00353 (19)	0.00407 (18)	0.00025 (18)
Cl2	0.0223 (3)	0.0131 (2)	0.0182 (2)	−0.00076 (19)	−0.00300 (19)	0.00130 (17)
OW1	0.0217 (9)	0.0156 (8)	0.0159 (7)	−0.0035 (7)	−0.0041 (6)	0.0015 (6)
N1	0.0128 (9)	0.0128 (7)	0.0124 (7)	−0.0003 (8)	0.0025 (5)	0.0011 (7)
C2	0.0192 (13)	0.0136 (10)	0.0145 (9)	0.0006 (7)	0.0046 (8)	−0.0014 (7)
C3	0.0221 (15)	0.0192 (10)	0.0143 (10)	0.0018 (9)	0.0031 (9)	−0.0006 (8)
C4	0.0189 (14)	0.0192 (10)	0.0156 (10)	0.0021 (8)	−0.0037 (8)	−0.0013 (7)
C5	0.0110 (11)	0.0289 (11)	0.0255 (10)	−0.0010 (11)	−0.0041 (7)	−0.0015 (11)
C6	0.0110 (13)	0.0279 (13)	0.0308 (12)	0.0031 (8)	0.0046 (9)	0.0026 (9)
C7	0.0197 (15)	0.0286 (11)	0.0267 (12)	0.0040 (9)	0.0131 (10)	0.0013 (9)
C8	0.0234 (15)	0.0258 (13)	0.0208 (12)	0.0028 (9)	0.0128 (9)	−0.0007 (8)
C9	0.0192 (13)	0.0183 (9)	0.0156 (10)	−0.0007 (8)	0.0064 (8)	0.0005 (8)
N10	0.0113 (11)	0.0158 (8)	0.0151 (8)	0.0006 (6)	0.0047 (7)	0.0010 (6)
C11	0.0136 (12)	0.0124 (9)	0.0168 (9)	−0.0005 (7)	0.0028 (8)	0.0009 (7)
C12	0.0134 (13)	0.0208 (10)	0.0210 (11)	0.0011 (8)	0.0062 (8)	0.0021 (8)
C13	0.0172 (12)	0.0147 (9)	0.0188 (9)	0.0015 (9)	0.0010 (7)	0.0025 (9)
C14	0.0125 (10)	0.0113 (8)	0.0162 (8)	0.0009 (9)	0.0024 (7)	0.0018 (8)
C15	0.0168 (14)	0.0328 (13)	0.0173 (10)	0.0003 (9)	0.0051 (9)	−0.0048 (9)
C16	0.0236 (16)	0.0352 (14)	0.0147 (11)	−0.0021 (10)	0.0055 (9)	−0.0055 (8)

Geometric parameters (Å, º)

Cu1—OW1	1.9582 (15)	C5—C13	1.425 (3)
Cu1—N1	1.9911 (15)	C6—C12	1.441 (3)
Cu1—N10	2.230 (2)	C7—C8	1.365 (4)
Cu1—Cl2	2.3017 (5)	C7—C12	1.409 (3)
Cu1—Cl1	2.3026 (6)	C8—C9	1.415 (4)
N1—C2	1.333 (3)	C9—N10	1.332 (3)
N1—C14	1.359 (3)	C9—C16	1.490 (4)
C2—C3	1.415 (3)	N10—C11	1.366 (3)
C2—C15	1.484 (4)	C11—C12	1.398 (4)
C3—C4	1.357 (4)	C11—C14	1.436 (3)
C4—C13	1.412 (3)	C13—C14	1.411 (3)
C5—C6	1.344 (3)
OW1—Cu1—N1	171.44 (7)	C8—C7—C12	118.9 (2)
OW1—Cu1—N10	107.34 (7)	C7—C8—C9	120.7 (2)
N1—Cu1—N10	79.98 (7)	N10—C9—C8	120.9 (2)
OW1—Cu1—Cl2	87.57 (5)	N10—C9—C16	118.1 (2)
N1—Cu1—Cl2	86.68 (6)	C8—C9—C16	121.0 (2)
N10—Cu1—Cl2	100.57 (5)	C9—N10—C11	118.9 (2)
OW1—Cu1—Cl1	87.77 (6)	C9—N10—Cu1	133.46 (16)
N1—Cu1—Cl1	94.84 (5)	C11—N10—Cu1	107.36 (14)
N10—Cu1—Cl1	103.92 (5)	N10—C11—C12	122.9 (2)
Cl2—Cu1—Cl1	155.36 (2)	N10—C11—C14	117.7 (2)
C2—N1—C14	120.47 (17)	C12—C11—C14	119.40 (19)
C2—N1—Cu1	123.98 (15)	C11—C12—C7	117.7 (2)
C14—N1—Cu1	114.81 (11)	C11—C12—C6	119.7 (2)
N1—C2—C3	119.7 (2)	C7—C12—C6	122.6 (3)
N1—C2—C15	118.81 (19)	C14—C13—C4	117.0 (2)
C3—C2—C15	121.45 (19)	C14—C13—C5	119.70 (18)
C4—C3—C2	121.0 (2)	C4—C13—C5	123.34 (19)
C3—C4—C13	119.7 (2)	N1—C14—C13	122.11 (17)
C6—C5—C13	121.0 (2)	N1—C14—C11	118.49 (17)
C5—C6—C12	120.8 (3)	C13—C14—C11	119.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
OW1—HW1···Cl1^i	0.77 (4)	2.36 (4)	3.0882 (17)	159 (3)
OW1—HW2···Cl2^ii	0.75 (4)	2.31 (4)	3.0286 (17)	162 (3)

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