Di-μ-chloro-bis{[N,N-bis(3,5-di­methyl­pyrazol-1-yl­methyl)-1-hydroxy­ethan­amine]copper(II)} dichloride dihydrate

The title compound, [Cu₂Cl₂(C₁₄H₂₃N₅O)₂]Cl₂·2H₂O, crystallizes with the dinuclear mol­ecule located on a centre of symmetry. The coordination geometry around the Cu atom is distorted octahedral, with three N atoms and one Cl atom in the equatorial plane, whereas the axial positions are occupied by the other Cl atom and the hydroxy group. There are two additional Cl⁻ anions and two water mol­ecules in the asymmetric unit. Infinite hydrogen-bonded chains involving O—H...Cl interactions are formed.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.109
• Data-to-parameter ratio = 19.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N1     -   C9      ..       7.08 su

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     -   C6      ..       5.10 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu     -   Cl1     ..       5.23 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu     -   O1      ..       5.82 su
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          3
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED, Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Di-µ-chloro-bis{[N,N-bis(3,5-dimethylpyrazol-1-ylmethyl)-1- hydroxyethanamine]copper(II)} dichloride dihydrate

Crystal data

[Cu2Cl2(C14H23N5O)2]Cl2·2H2O	Z = 1
Mr = 859.67	F(000) = 446
Triclinic, P1	Dx = 1.518 Mg m^−3
Hall symbol: -P 1	Melting point: 431 K
a = 8.5418 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.1878 (8) Å	Cell parameters from 5565 reflections
c = 11.6189 (7) Å	θ = 3.0–30.3°
α = 66.625 (6)°	µ = 1.46 mm^−1
β = 69.332 (6)°	T = 293 K
γ = 73.642 (6)°	Parallelepiped, blue
V = 940.57 (11) Å^3	0.32 × 0.15 × 0.13 mm

Data collection

Xcalibur CCD diffractometer	3849 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.062
Graphite monochromator	θmax = 28.0°, θmin = 3.0°
Detector resolution: 0 pixels mm^-1	h = −11→11
ω scans	k = −14→14
15083 measured reflections	l = −15→15
4526 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0617P)^2 + 0.1229P] where P = (Fo^2 + 2Fc^2)/3
4526 reflections	(Δ/σ)max = 0.001
231 parameters	Δρmax = 0.72 e Å^−3
0 restraints	Δρmin = −0.67 e Å^−3

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	Occ. (<1)
Cu	0.48998 (3)	0.32765 (2)	0.60920 (2)	0.02758 (10)
Cl1	0.72985 (7)	0.41176 (6)	0.49055 (5)	0.03942 (14)
Cl2	0.89277 (8)	0.02805 (7)	0.82939 (7)	0.05261 (18)
N2	0.2951 (2)	0.23915 (17)	0.51765 (16)	0.0304 (4)
O1	0.5928 (2)	0.10932 (17)	0.71825 (16)	0.0392 (4)
HO1	0.675 (4)	0.097 (3)	0.732 (3)	0.054 (9)*
N5	0.4498 (2)	0.37661 (17)	0.76851 (17)	0.0301 (4)
N3	0.4518 (2)	0.27424 (18)	0.47693 (16)	0.0308 (4)
N4	0.2943 (2)	0.35245 (18)	0.85382 (16)	0.0316 (4)
O2	1.1573 (3)	−0.1835 (2)	0.9781 (2)	0.0651 (6)
HO21	1.092 (4)	−0.122 (3)	0.926 (3)	0.050*
HO22	1.150 (4)	−0.147 (3)	1.037 (3)	0.050*
N1	0.26180 (19)	0.25376 (16)	0.72059 (15)	0.0236 (3)
C1	0.1236 (4)	0.1330 (3)	0.4618 (3)	0.0565 (7)
H1A	0.0863	0.0802	0.5516	0.085*
H1B	0.1470	0.0805	0.4074	0.085*
H1C	0.0364	0.2068	0.4403	0.085*
C2	0.2809 (3)	0.1817 (2)	0.4400 (2)	0.0377 (5)
C3	0.4331 (3)	0.1806 (3)	0.3461 (3)	0.0455 (6)
H3	0.4616	0.1481	0.2778	0.055*
C4	0.5372 (3)	0.2376 (2)	0.3723 (2)	0.0395 (5)
C5	0.7152 (3)	0.2578 (4)	0.2989 (3)	0.0597 (8)
H5A	0.7525	0.3042	0.3359	0.090*	0.50
H5B	0.7208	0.3086	0.2092	0.090*	0.50
H5C	0.7871	0.1737	0.3044	0.090*	0.50
H5D	0.7544	0.2201	0.2305	0.090*	0.50
H5E	0.7861	0.2157	0.3571	0.090*	0.50
H5F	0.7198	0.3506	0.2620	0.090*	0.50
C6	0.1706 (2)	0.2758 (2)	0.62535 (19)	0.0292 (4)
H6A	0.0819	0.2219	0.6644	0.035*
H6B	0.1193	0.3678	0.5957	0.035*
C7	0.2974 (3)	0.1108 (2)	0.7941 (2)	0.0344 (4)
H7A	0.3041	0.0605	0.7405	0.041*
H7B	0.2037	0.0882	0.8716	0.041*
C8	0.4596 (3)	0.0712 (2)	0.8339 (2)	0.0370 (5)
H8A	0.4521	0.1153	0.8931	0.044*
H8B	0.4805	−0.0234	0.8774	0.044*
C9	0.1709 (3)	0.3352 (2)	0.8048 (2)	0.0324 (4)
H9A	0.1187	0.4202	0.7554	0.039*
H9B	0.0827	0.2917	0.8765	0.039*
C10	0.1282 (4)	0.3277 (3)	1.0852 (2)	0.0531 (7)
H10A	0.0306	0.3852	1.0590	0.080*
H10B	0.1403	0.3447	1.1561	0.080*
H10C	0.1140	0.2375	1.1126	0.080*
C11	0.2831 (3)	0.3524 (2)	0.9729 (2)	0.0369 (5)
C12	0.4357 (3)	0.3771 (2)	0.9638 (2)	0.0421 (5)
H12	0.4665	0.3832	1.0302	0.051*
C13	0.5366 (3)	0.3916 (2)	0.8363 (2)	0.0340 (4)
C14	0.7126 (3)	0.4198 (3)	0.7795 (3)	0.0454 (6)
H14A	0.7840	0.3530	0.7431	0.068*
H14B	0.7536	0.4201	0.8464	0.068*
H14C	0.7142	0.5045	0.7123	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu	0.02434 (15)	0.03356 (16)	0.02579 (15)	−0.01258 (10)	−0.00170 (10)	−0.01000 (11)
Cl1	0.0297 (3)	0.0426 (3)	0.0407 (3)	−0.0175 (2)	0.0021 (2)	−0.0110 (2)
Cl2	0.0427 (3)	0.0604 (4)	0.0564 (4)	−0.0156 (3)	−0.0231 (3)	−0.0080 (3)
N2	0.0280 (8)	0.0366 (9)	0.0299 (8)	−0.0107 (7)	−0.0059 (7)	−0.0123 (7)
O1	0.0297 (8)	0.0455 (9)	0.0413 (9)	−0.0065 (7)	−0.0121 (7)	−0.0110 (7)
N5	0.0280 (8)	0.0342 (9)	0.0308 (9)	−0.0111 (7)	−0.0052 (7)	−0.0118 (7)
N3	0.0273 (8)	0.0364 (9)	0.0288 (8)	−0.0091 (7)	−0.0028 (7)	−0.0127 (7)
N4	0.0290 (8)	0.0402 (9)	0.0278 (8)	−0.0143 (7)	−0.0006 (7)	−0.0136 (7)
O2	0.0809 (16)	0.0545 (12)	0.0597 (13)	−0.0067 (11)	−0.0299 (12)	−0.0124 (10)
N1	0.0225 (7)	0.0273 (8)	0.0211 (7)	−0.0083 (6)	−0.0037 (6)	−0.0072 (6)
C1	0.0575 (16)	0.0748 (19)	0.0597 (17)	−0.0276 (14)	−0.0174 (13)	−0.0324 (15)
C2	0.0428 (12)	0.0385 (11)	0.0388 (11)	−0.0072 (9)	−0.0163 (10)	−0.0151 (9)
C3	0.0498 (14)	0.0532 (14)	0.0454 (13)	−0.0037 (11)	−0.0141 (11)	−0.0304 (12)
C4	0.0377 (12)	0.0465 (13)	0.0360 (11)	−0.0009 (10)	−0.0076 (9)	−0.0218 (10)
C5	0.0377 (13)	0.093 (2)	0.0554 (16)	−0.0134 (14)	0.0076 (11)	−0.0471 (17)
C6	0.0233 (9)	0.0356 (10)	0.0300 (10)	−0.0098 (7)	−0.0040 (7)	−0.0115 (8)
C7	0.0344 (11)	0.0312 (10)	0.0351 (11)	−0.0130 (8)	−0.0100 (9)	−0.0030 (8)
C8	0.0422 (12)	0.0340 (11)	0.0346 (11)	−0.0087 (9)	−0.0166 (9)	−0.0042 (9)
C9	0.0262 (9)	0.0419 (11)	0.0285 (10)	−0.0116 (8)	−0.0015 (8)	−0.0120 (9)
C10	0.0633 (17)	0.0644 (17)	0.0324 (12)	−0.0273 (13)	0.0057 (11)	−0.0218 (12)
C11	0.0478 (13)	0.0364 (11)	0.0281 (10)	−0.0145 (9)	−0.0042 (9)	−0.0126 (9)
C12	0.0565 (14)	0.0457 (13)	0.0349 (11)	−0.0189 (11)	−0.0157 (10)	−0.0142 (10)
C13	0.0360 (11)	0.0329 (10)	0.0391 (11)	−0.0104 (8)	−0.0141 (9)	−0.0114 (9)
C14	0.0376 (12)	0.0576 (15)	0.0499 (14)	−0.0161 (11)	−0.0163 (10)	−0.0172 (12)

Geometric parameters (Å, º)

Cu—N3	2.0045 (17)	C4—C5	1.488 (4)
Cu—N5	2.0233 (17)	C5—H5A	0.9600
Cu—N1	2.1060 (15)	C5—H5B	0.9600
Cu—Cl1	2.2465 (5)	C5—H5C	0.9600
Cu—O1	2.3375 (18)	C5—H5D	0.9600
Cu—Cl1^i	3.0233 (7)	C5—H5E	0.9600
N2—C2	1.350 (3)	C5—H5F	0.9600
N2—N3	1.368 (2)	C6—H6A	0.9700
N2—C6	1.445 (2)	C6—H6B	0.9700
O1—C8	1.421 (3)	C7—C8	1.508 (3)
O1—HO1	0.74 (3)	C7—H7A	0.9700
N5—C13	1.337 (3)	C7—H7B	0.9700
N5—N4	1.371 (2)	C8—H8A	0.9700
N3—C4	1.334 (3)	C8—H8B	0.9700
N4—C11	1.353 (3)	C9—H9A	0.9700
N4—C9	1.448 (3)	C9—H9B	0.9700
O2—HO21	0.92 (3)	C10—C11	1.493 (3)
O2—HO22	0.90 (3)	C10—H10A	0.9600
N1—C9	1.471 (3)	C10—H10B	0.9600
N1—C6	1.475 (2)	C10—H10C	0.9600
N1—C7	1.485 (3)	C11—C12	1.367 (3)
C1—C2	1.493 (3)	C12—C13	1.397 (3)
C1—H1A	0.9600	C12—H12	0.9300
C1—H1B	0.9600	C13—C14	1.482 (3)
C1—H1C	0.9600	C14—H14A	0.9600
C2—C3	1.371 (3)	C14—H14B	0.9600
C3—C4	1.397 (3)	C14—H14C	0.9600
C3—H3	0.9300
N3—Cu—N5	161.77 (7)	H5A—C5—H5D	141.1
N3—Cu—N1	81.14 (6)	H5B—C5—H5D	56.3
N5—Cu—N1	81.42 (6)	H5C—C5—H5D	56.3
N3—Cu—Cl1	99.50 (5)	C4—C5—H5E	109.5
N5—Cu—Cl1	97.81 (5)	H5A—C5—H5E	56.3
N1—Cu—Cl1	178.50 (4)	H5B—C5—H5E	141.1
N3—Cu—O1	91.59 (7)	H5C—C5—H5E	56.3
N5—Cu—O1	90.26 (7)	H5D—C5—H5E	109.5
N1—Cu—O1	78.94 (6)	C4—C5—H5F	109.5
Cl1—Cu—O1	102.37 (5)	H5A—C5—H5F	56.3
N3—Cu—Cl1^i	86.70 (5)	H5B—C5—H5F	56.3
N5—Cu—Cl1^i	86.93 (5)	H5C—C5—H5F	141.1
N1—Cu—Cl1^i	86.37 (4)	H5D—C5—H5F	109.5
Cl1—Cu—Cl1^i	92.30 (2)	H5E—C5—H5F	109.5
O1—Cu—Cl1^i	165.30 (4)	N2—C6—N1	106.50 (15)
C2—N2—N3	111.24 (17)	N2—C6—H6A	110.4
C2—N2—C6	130.47 (17)	N1—C6—H6A	110.4
N3—N2—C6	118.10 (15)	N2—C6—H6B	110.4
C8—O1—Cu	104.17 (12)	N1—C6—H6B	110.4
C8—O1—HO1	112 (3)	H6A—C6—H6B	108.6
Cu—O1—HO1	117 (3)	N1—C7—C8	113.28 (16)
C13—N5—N4	105.74 (17)	N1—C7—H7A	108.9
C13—N5—Cu	140.16 (15)	C8—C7—H7A	108.9
N4—N5—Cu	110.99 (12)	N1—C7—H7B	108.9
C4—N3—N2	106.16 (17)	C8—C7—H7B	108.9
C4—N3—Cu	140.84 (16)	H7A—C7—H7B	107.7
N2—N3—Cu	111.49 (12)	O1—C8—C7	107.19 (17)
C11—N4—N5	111.39 (17)	O1—C8—H8A	110.3
C11—N4—C9	130.88 (17)	C7—C8—H8A	110.3
N5—N4—C9	117.70 (16)	O1—C8—H8B	110.3
HO21—O2—HO22	105 (3)	C7—C8—H8B	110.3
C9—N1—C6	110.99 (15)	H8A—C8—H8B	108.5
C9—N1—C7	113.52 (16)	N4—C9—N1	107.24 (16)
C6—N1—C7	110.62 (15)	N4—C9—H9A	110.3
C9—N1—Cu	105.47 (11)	N1—C9—H9A	110.3
C6—N1—Cu	105.37 (11)	N4—C9—H9B	110.3
C7—N1—Cu	110.44 (12)	N1—C9—H9B	110.3
C2—C1—H1A	109.5	H9A—C9—H9B	108.5
C2—C1—H1B	109.5	C11—C10—H10A	109.5
H1A—C1—H1B	109.5	C11—C10—H10B	109.5
C2—C1—H1C	109.5	H10A—C10—H10B	109.5
H1A—C1—H1C	109.5	C11—C10—H10C	109.5
H1B—C1—H1C	109.5	H10A—C10—H10C	109.5
N2—C2—C3	106.2 (2)	H10B—C10—H10C	109.5
N2—C2—C1	122.9 (2)	N4—C11—C12	106.07 (19)
C3—C2—C1	131.0 (2)	N4—C11—C10	122.9 (2)
C2—C3—C4	107.2 (2)	C12—C11—C10	131.0 (2)
C2—C3—H3	126.4	C11—C12—C13	107.36 (19)
C4—C3—H3	126.4	C11—C12—H12	126.3
N3—C4—C3	109.2 (2)	C13—C12—H12	126.3
N3—C4—C5	123.0 (2)	N5—C13—C12	109.44 (19)
C3—C4—C5	127.8 (2)	N5—C13—C14	123.2 (2)
C4—C5—H5A	109.5	C12—C13—C14	127.3 (2)
C4—C5—H5B	109.5	C13—C14—H14A	109.5
H5A—C5—H5B	109.5	C13—C14—H14B	109.5
C4—C5—H5C	109.5	H14A—C14—H14B	109.5
H5A—C5—H5C	109.5	C13—C14—H14C	109.5
H5B—C5—H5C	109.5	H14A—C14—H14C	109.5
C4—C5—H5D	109.5	H14B—C14—H14C	109.5
N3—Cu—O1—C8	−106.53 (13)	O1—Cu—N1—C7	−3.18 (12)
N5—Cu—O1—C8	55.33 (13)	N3—N2—C2—C3	−0.4 (3)
N1—Cu—O1—C8	−25.88 (13)	C6—N2—C2—C3	174.5 (2)
Cl1—Cu—O1—C8	153.39 (12)	N3—N2—C2—C1	179.8 (2)
Cl1^i—Cu—O1—C8	−23.5 (3)	C6—N2—C2—C1	−5.4 (4)
N3—Cu—N5—C13	166.1 (2)	N2—C2—C3—C4	0.8 (3)
N1—Cu—N5—C13	148.9 (2)	C1—C2—C3—C4	−179.3 (3)
Cl1—Cu—N5—C13	−32.4 (2)	N2—N3—C4—C3	0.7 (3)
O1—Cu—N5—C13	70.2 (2)	Cu—N3—C4—C3	164.39 (19)
Cl1^i—Cu—N5—C13	−124.3 (2)	N2—N3—C4—C5	−179.6 (2)
N3—Cu—N5—N4	10.1 (3)	Cu—N3—C4—C5	−15.9 (4)
N1—Cu—N5—N4	−7.02 (13)	C2—C3—C4—N3	−1.0 (3)
Cl1—Cu—N5—N4	171.67 (13)	C2—C3—C4—C5	179.4 (3)
O1—Cu—N5—N4	−85.80 (14)	C2—N2—C6—N1	144.9 (2)
Cl1^i—Cu—N5—N4	79.76 (13)	N3—N2—C6—N1	−40.5 (2)
C2—N2—N3—C4	−0.2 (2)	C9—N1—C6—N2	156.65 (15)
C6—N2—N3—C4	−175.77 (18)	C7—N1—C6—N2	−76.41 (19)
C2—N2—N3—Cu	−169.23 (15)	Cu—N1—C6—N2	42.96 (16)
C6—N2—N3—Cu	15.2 (2)	C9—N1—C7—C8	−86.2 (2)
N5—Cu—N3—C4	−171.3 (2)	C6—N1—C7—C8	148.23 (18)
N1—Cu—N3—C4	−154.2 (3)	Cu—N1—C7—C8	32.0 (2)
Cl1—Cu—N3—C4	27.2 (3)	Cu—O1—C8—C7	48.40 (18)
O1—Cu—N3—C4	−75.7 (3)	N1—C7—C8—O1	−57.0 (2)
Cl1^i—Cu—N3—C4	118.9 (3)	C11—N4—C9—N1	−140.3 (2)
N5—Cu—N3—N2	−8.2 (3)	N5—N4—C9—N1	41.7 (2)
N1—Cu—N3—N2	8.91 (13)	C6—N1—C9—N4	−156.21 (16)
Cl1—Cu—N3—N2	−169.71 (12)	C7—N1—C9—N4	78.46 (19)
O1—Cu—N3—N2	87.46 (14)	Cu—N1—C9—N4	−42.58 (17)
Cl1^i—Cu—N3—N2	−77.93 (13)	N5—N4—C11—C12	0.0 (3)
C13—N5—N4—C11	0.1 (2)	C9—N4—C11—C12	−178.2 (2)
Cu—N5—N4—C11	164.38 (15)	N5—N4—C11—C10	−179.6 (2)
C13—N5—N4—C9	178.53 (18)	C9—N4—C11—C10	2.3 (4)
Cu—N5—N4—C9	−17.2 (2)	N4—C11—C12—C13	−0.1 (3)
N3—Cu—N1—C9	−146.76 (13)	C10—C11—C12—C13	179.4 (3)
N5—Cu—N1—C9	27.89 (13)	N4—N5—C13—C12	−0.1 (2)
O1—Cu—N1—C9	119.85 (13)	Cu—N5—C13—C12	−156.87 (19)
N3—Cu—N1—C6	−29.27 (12)	N4—N5—C13—C14	−179.8 (2)
N5—Cu—N1—C6	145.38 (13)	Cu—N5—C13—C14	23.4 (4)
O1—Cu—N1—C6	−122.67 (12)	C11—C12—C13—N5	0.1 (3)
N3—Cu—N1—C7	90.21 (13)	C11—C12—C13—C14	179.8 (2)
N5—Cu—N1—C7	−95.14 (13)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—HO1···Cl2	0.74 (3)	2.30 (3)	3.0255 (18)	165 (3)
O2—HO21···Cl2	0.92 (3)	2.29 (3)	3.192 (2)	170 (3)
O2—HO22···Cl2^ii	0.90 (3)	2.30 (3)	3.194 (3)	172 (3)

Symmetry code: (ii) −x+2, −y, −z+2.