Azido­{1-[2-(propyl­amino)ethyl­imino­meth­yl]naphthalen-2-olato}copper(II)

Zhu, C.-G.; Wei, Y.-J.; Wang, F.-W.

doi:10.1107/S1600536807062514

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Azido{1-[2-(propylamino)ethyliminomethyl]naphthalen-2-olato}copper(II)

C.-G. Zhu, Y.-J. Wei and F.-W. Wang

The title compound, [Cu(C₁₆H₁₉N₂O)(N₃)], was synthesized by the reaction of equimolar quantities of 2-hydroxy-1-naphthaldehyde, N-propylethane-1,2-diamine, sodium azide and copper(II) acetate in a methanol solution. The Cu^II ion in the compound is four-coordinated by one imine N, one amine N, and one phenolate O atoms of the Schiff base ligand 1-[2-(propylamino)ethyliminomethyl]naphthalen-2-ol and by one terminal N atom of an azide anion, forming a square-planar coordination. The propyl group and attached NH are disordered over two positions; the site occupancy factors are ca 0.6 and 0.4.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807062514/gd2027sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807062514/gd2027Isup2.hkl Contains datablock I

CCDC reference: 672777

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.013 Å
Disorder in main residue
R factor = 0.069
wR factor = 0.214
Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......          4
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.75 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.39 Ratio
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C13
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for       C14'
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for       C15'
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C15

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C8
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N2'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT301_ALERT_3_C Main Residue  Disorder .........................      15.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         13
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         12

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

During the last few years, there has been a great effort to identify the biological role of copper (Collinson & Fenton, 1996; Hossain et al., 1996; Tarafder et al., 2002). It appears that the biological role of copper is primarily in redox reactions and as a biological catalyst, although much remains to be understood (Musie et al., 2003; García-Raso et al., 2003). The peculiarity of copper lies in its ability to form complexes with coordination number four, five, and six (Ray et al., 2003; Arnold et al., 2003; Raptopoulou et al., 1998). Recently, we have reported several Schiff base copper(II) complexes with azide ligand (Zhu et al., 2006; Wei & Wang, 2006). Here the structure of the title complex (I), Fig. 1, is reported.

Complex (I) is a mononuclear copper(II) compound. The Cu^II ion is four-coordinated by one imine N, one amine N, and one phenolate O atoms of a Schiff base ligand, and by one terminal N atom of an azide anion, forming a square planar coordination. All the bond lengths are in normal ranges (Allen et al., 1987). The bond lengths (Table 1) related to the Cu^II ion are comparable to the values of the complexes we reported previously corresponding, and also comparable to the values of other Schiff base copper(II) complexes (Hebbachi & Benali-Cherif, 2005; Butcher et al., 2003). The bond angles around the central metal ion show somewhat deviations from ideal square planar geometry, ranging from 87.2 (2) to 93.8 (2) °. The two trans bond angles are 177.3 (2) and 177.8 (2) °, respectively.

Related literature top

For related literature, see: Allen et al. (1987); Arnold et al. (2003); Collinson & Fenton (1996); García-Raso et al. (2003); Hossain et al. (1996); Musie et al. (2003); Raptopoulou et al. (1998); Ray et al. (2003); Tarafder et al. (2002); Wei & Wang (2006); Zhu et al. (2006); Butcher (2003); Hebbachi & Benali-Cherif (2005).

Experimental top

2-Hydroxy-1-naphthaldehyde (1.0 mmol, 172.3 mg), N-propylethane-1,2-diamine (1.0 mmol, 102.2 mg), sodium azide (1.0 mmol, 65.0 mg), and copper acetate (1.0 mmol, 199.1 mg) were dissolved in a methanol solution (150 ml). The mixture was refluxed at 340 K for about 1 h to give a clear blue solution. After keeping the cooled resulting solution in dark for 12 days, blue block-shaped crystals were formed.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top

Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Only the major orientation of the disordered propyl group is shown.

Azido{1-[2-(propylamino)ethyliminomethyl]naphthalen-2-olato}copper(II) top

Crystal data top

[Cu(C₁₆H₁₉N₂O)(N₃)]	F(000) = 1496
M_r = 360.90	D_x = 1.442 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.465 (4) Å	Cell parameters from 1297 reflections
b = 24.772 (8) Å	θ = 2.4–24.5°
c = 11.047 (4) Å	µ = 1.33 mm⁻¹
β = 103.007 (4)°	T = 298 K
V = 3323.7 (19) Å³	Block, blue
Z = 8	0.20 × 0.20 × 0.18 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3452 independent reflections
Radiation source: fine-focus sealed tube	1816 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
ω scan	θ_max = 26.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.778, T_max = 0.796	k = −31→31
13362 measured reflections	l = −13→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.214	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0886P)² + 3.7952P] where P = (F_o² + 2F_c²)/3
3452 reflections	(Δ/σ)_max < 0.001
201 parameters	Δρ_max = 0.53 e Å⁻³
12 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Cu(C₁₆H₁₉N₂O)(N₃)]	V = 3323.7 (19) Å³
M_r = 360.90	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 12.465 (4) Å	µ = 1.33 mm⁻¹
b = 24.772 (8) Å	T = 298 K
c = 11.047 (4) Å	0.20 × 0.20 × 0.18 mm
β = 103.007 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3452 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1816 reflections with I > 2σ(I)
T_min = 0.778, T_max = 0.796	R_int = 0.069
13362 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	12 restraints
wR(F²) = 0.214	H-atom parameters constrained
S = 1.01	Δρ_max = 0.53 e Å⁻³
3452 reflections	Δρ_min = −0.30 e Å⁻³
201 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cu1	0.12391 (5)	0.23867 (3)	0.35451 (7)	0.0733 (4)
O1	0.1921 (3)	0.19640 (17)	0.2615 (4)	0.0785 (11)
N1	0.0746 (4)	0.1811 (2)	0.4326 (4)	0.0701 (13)
N3	0.1703 (5)	0.2997 (2)	0.2755 (6)	0.0891 (16)
N4	0.2368 (4)	0.2975 (2)	0.2131 (5)	0.0789 (14)
N5	0.2984 (5)	0.2977 (3)	0.1539 (6)	0.120 (2)
C1	0.1459 (5)	0.1089 (3)	0.3270 (6)	0.0715 (16)
C2	0.1936 (5)	0.1440 (3)	0.2545 (6)	0.0739 (16)
C3	0.2508 (6)	0.1221 (3)	0.1681 (7)	0.098 (2)
H3	0.2832	0.1450	0.1200	0.117*
C4	0.2585 (7)	0.0675 (4)	0.1554 (8)	0.114 (3)
H4	0.2952	0.0540	0.0973	0.137*
C5	0.2128 (7)	0.0310 (3)	0.2272 (8)	0.101 (2)
C6	0.2267 (8)	−0.0239 (4)	0.2101 (11)	0.136 (3)
H6	0.2666	−0.0364	0.1540	0.163*
C7	0.1800 (12)	−0.0588 (4)	0.2783 (14)	0.158 (5)
H7	0.1882	−0.0957	0.2675	0.190*
C8	0.1220 (11)	−0.0419 (5)	0.3614 (12)	0.156 (5)
H8	0.0907	−0.0669	0.4060	0.187*
C9	0.1097 (7)	0.0133 (4)	0.3796 (8)	0.118 (3)
H9	0.0705	0.0250	0.4371	0.142*
C10	0.1555 (6)	0.0514 (3)	0.3125 (7)	0.0852 (19)
C11	0.0889 (5)	0.1310 (3)	0.4126 (6)	0.0762 (17)
H11	0.0585	0.1065	0.4593	0.091*
C12	0.0082 (6)	0.1975 (4)	0.5219 (7)	0.105 (2)
H12A	−0.0692	0.1909	0.4866	0.126*
H12B	0.0297	0.1765	0.5977	0.126*
C13	0.0263 (8)	0.2541 (4)	0.5491 (9)	0.128 (3)
H13A	−0.0377	0.2688	0.5738	0.154*
H13B	0.0889	0.2581	0.6188	0.154*
N2	0.0461 (5)	0.2847 (2)	0.4465 (5)	0.0914 (16)*	0.37 (3)
H2A	−0.0223	0.2847	0.3955	0.110*	0.37 (3)
C14	0.0697 (19)	0.3422 (4)	0.455 (3)	0.081 (7)*	0.37 (3)
H14A	0.0946	0.3517	0.3801	0.097*	0.37 (3)
H14B	0.1324	0.3470	0.5238	0.097*	0.37 (3)
C15	−0.012 (2)	0.3832 (10)	0.469 (4)	0.127 (11)*	0.37 (3)
H15A	−0.0178	0.3832	0.5548	0.153*	0.37 (3)
H15B	−0.0826	0.3727	0.4183	0.153*	0.37 (3)
C16	0.012 (4)	0.4387 (13)	0.435 (6)	0.27 (2)*	0.37 (3)
H16A	−0.0458	0.4622	0.4464	0.399*	0.37 (3)
H16B	0.0173	0.4395	0.3496	0.399*	0.37 (3)
H16C	0.0808	0.4503	0.4869	0.399*	0.37 (3)
N2'	0.0461 (5)	0.2847 (2)	0.4465 (5)	0.0914 (16)*	0.63 (3)
H2'A	−0.0210	0.2911	0.3959	0.110*	0.63 (3)
C14'	0.0896 (14)	0.3366 (5)	0.492 (2)	0.138 (8)*	0.63 (3)
H14C	0.1101	0.3559	0.4239	0.166*	0.63 (3)
H14D	0.1562	0.3310	0.5554	0.166*	0.63 (3)
C15'	0.0149 (12)	0.3708 (5)	0.5433 (19)	0.107 (6)*	0.63 (3)
H15C	0.0287	0.3647	0.6322	0.129*	0.63 (3)
H15D	−0.0603	0.3598	0.5076	0.129*	0.63 (3)
C16'	0.0258 (16)	0.4291 (6)	0.520 (2)	0.158 (8)*	0.63 (3)
H16D	−0.0282	0.4487	0.5523	0.236*	0.63 (3)
H16E	0.0146	0.4354	0.4326	0.236*	0.63 (3)
H16F	0.0982	0.4410	0.5612	0.236*	0.63 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0607 (5)	0.0843 (6)	0.0809 (6)	−0.0013 (3)	0.0286 (4)	0.0000 (4)
O1	0.086 (3)	0.072 (3)	0.092 (3)	−0.001 (2)	0.050 (2)	0.001 (2)
N1	0.061 (3)	0.090 (4)	0.063 (3)	−0.012 (3)	0.023 (2)	0.002 (3)
N3	0.092 (4)	0.071 (3)	0.115 (4)	0.001 (3)	0.048 (3)	0.008 (3)
N4	0.071 (3)	0.067 (3)	0.105 (4)	−0.007 (3)	0.034 (3)	0.009 (3)
N5	0.119 (5)	0.110 (5)	0.157 (6)	−0.005 (4)	0.085 (5)	0.026 (4)
C1	0.058 (3)	0.072 (4)	0.079 (4)	−0.011 (3)	0.004 (3)	0.006 (3)
C2	0.067 (4)	0.073 (4)	0.087 (4)	0.001 (3)	0.028 (3)	0.001 (3)
C3	0.099 (5)	0.100 (6)	0.105 (5)	−0.003 (4)	0.046 (4)	−0.007 (4)
C4	0.108 (6)	0.098 (6)	0.142 (7)	0.014 (5)	0.042 (5)	−0.034 (6)
C5	0.098 (5)	0.071 (5)	0.124 (7)	0.002 (4)	0.007 (5)	−0.004 (5)
C6	0.146 (8)	0.085 (7)	0.163 (9)	0.020 (6)	0.005 (7)	−0.004 (6)
C7	0.176 (12)	0.079 (7)	0.189 (13)	0.019 (7)	−0.025 (9)	0.005 (8)
C8	0.189 (13)	0.085 (8)	0.178 (12)	−0.026 (7)	0.006 (9)	0.038 (7)
C9	0.122 (7)	0.106 (7)	0.118 (6)	−0.017 (5)	0.011 (5)	0.029 (5)
C10	0.080 (4)	0.077 (5)	0.090 (5)	−0.008 (4)	0.002 (4)	0.011 (4)
C11	0.069 (4)	0.090 (5)	0.071 (4)	−0.019 (3)	0.017 (3)	0.013 (4)
C12	0.102 (5)	0.144 (7)	0.087 (5)	−0.032 (5)	0.061 (4)	−0.015 (5)
C13	0.160 (7)	0.133 (6)	0.109 (5)	0.024 (5)	0.068 (5)	0.002 (5)

Geometric parameters (Å, º) top

Cu1—O1	1.808 (4)	C11—H11	0.9300
Cu1—N1	1.843 (5)	C12—C13	1.441 (11)
Cu1—N3	1.900 (5)	C12—H12A	0.9700
Cu1—N2	1.928 (6)	C12—H12B	0.9700
O1—C2	1.301 (7)	C13—N2	1.430 (9)
N1—C11	1.278 (8)	C13—H13A	0.9700
N1—C12	1.480 (7)	C13—H13B	0.9700
N3—N4	1.193 (7)	N2—C14	1.454 (9)
N4—N5	1.116 (7)	N2—H2A	0.9100
C1—C2	1.402 (8)	C14—C15	1.468 (10)
C1—C11	1.414 (9)	C14—H14A	0.9700
C1—C10	1.442 (9)	C14—H14B	0.9700
C2—C3	1.421 (9)	C15—C16	1.471 (10)
C3—C4	1.365 (10)	C15—H15A	0.9700
C3—H3	0.9300	C15—H15B	0.9700
C4—C5	1.405 (11)	C16—H16A	0.9600
C4—H4	0.9300	C16—H16B	0.9600
C5—C6	1.390 (11)	C16—H16C	0.9600
C5—C10	1.398 (10)	C14'—C15'	1.465 (9)
C6—C7	1.360 (15)	C14'—H14C	0.9700
C6—H6	0.9300	C14'—H14D	0.9700
C7—C8	1.357 (15)	C15'—C16'	1.478 (9)
C7—H7	0.9300	C15'—H15C	0.9700
C8—C9	1.397 (14)	C15'—H15D	0.9700
C8—H8	0.9300	C16'—H16D	0.9600
C9—C10	1.398 (10)	C16'—H16E	0.9600
C9—H9	0.9300	C16'—H16F	0.9600

O1—Cu1—N1	93.8 (2)	C13—C12—H12B	109.9
O1—Cu1—N3	88.3 (2)	N1—C12—H12B	109.9
N1—Cu1—N3	177.8 (2)	H12A—C12—H12B	108.3
O1—Cu1—N2	177.3 (2)	N2—C13—C12	113.4 (7)
N1—Cu1—N2	87.2 (2)	N2—C13—H13A	108.9
N3—Cu1—N2	90.7 (2)	C12—C13—H13A	108.9
C2—O1—Cu1	128.8 (4)	N2—C13—H13B	108.9
C11—N1—C12	120.2 (5)	C12—C13—H13B	108.9
C11—N1—Cu1	126.6 (4)	H13A—C13—H13B	107.7
C12—N1—Cu1	113.2 (5)	C13—N2—C14	122.7 (12)
N4—N3—Cu1	123.4 (5)	C13—N2—Cu1	107.6 (5)
N5—N4—N3	176.9 (7)	C14—N2—Cu1	119.5 (9)
C2—C1—C11	118.9 (6)	C13—N2—H2A	100.7
C2—C1—C10	119.5 (6)	C14—N2—H2A	100.7
C11—C1—C10	121.6 (6)	Cu1—N2—H2A	100.7
O1—C2—C1	124.9 (6)	N2—C14—C15	123.3 (17)
O1—C2—C3	115.9 (6)	N2—C14—H14A	106.5
C1—C2—C3	119.2 (6)	C15—C14—H14A	106.5
C4—C3—C2	120.3 (7)	N2—C14—H14B	106.5
C4—C3—H3	119.8	C15—C14—H14B	106.5
C2—C3—H3	119.8	H14A—C14—H14B	106.5
C3—C4—C5	122.2 (7)	C14—C15—C16	116 (3)
C3—C4—H4	118.9	C14—C15—H15A	108.3
C5—C4—H4	118.9	C16—C15—H15A	108.3
C6—C5—C10	122.9 (9)	C14—C15—H15B	108.3
C6—C5—C4	118.3 (10)	C16—C15—H15B	108.3
C10—C5—C4	118.8 (7)	H15A—C15—H15B	107.4
C7—C6—C5	117.7 (11)	C15—C16—H16A	109.5
C7—C6—H6	121.1	C15—C16—H16B	109.5
C5—C6—H6	121.1	H16A—C16—H16B	109.5
C8—C7—C6	122.6 (11)	C15—C16—H16C	109.5
C8—C7—H7	118.7	H16A—C16—H16C	109.5
C6—C7—H7	118.7	H16B—C16—H16C	109.5
C7—C8—C9	119.5 (11)	C15'—C14'—H14C	108.4
C7—C8—H8	120.3	C15'—C14'—H14D	108.4
C9—C8—H8	120.3	H14C—C14'—H14D	107.5
C8—C9—C10	120.9 (10)	C14'—C15'—C16'	114.0 (12)
C8—C9—H9	119.6	C14'—C15'—H15C	108.8
C10—C9—H9	119.6	C16'—C15'—H15C	108.8
C9—C10—C5	116.5 (8)	C14'—C15'—H15D	108.8
C9—C10—C1	123.6 (8)	C16'—C15'—H15D	108.8
C5—C10—C1	120.0 (6)	H15C—C15'—H15D	107.6
N1—C11—C1	127.0 (5)	C15'—C16'—H16D	109.5
N1—C11—H11	116.5	C15'—C16'—H16E	109.5
C1—C11—H11	116.5	H16D—C16'—H16E	109.5
C13—C12—N1	108.8 (6)	C15'—C16'—H16F	109.5
C13—C12—H12A	109.9	H16D—C16'—H16F	109.5
N1—C12—H12A	109.9	H16E—C16'—H16F	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2′—H2′A···N3ⁱ	0.91	2.35	3.233 (8)	165
N2—H2A···N3ⁱ	0.91	2.35	3.233 (8)	162

Symmetry code: (i) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₆H₁₉N₂O)(N₃)]
M_r	360.90
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	12.465 (4), 24.772 (8), 11.047 (4)
β (°)	103.007 (4)
V (Å³)	3323.7 (19)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.33
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.778, 0.796
No. of measured, independent and observed [I > 2σ(I)] reflections	13362, 3452, 1816
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.214, 1.01
No. of reflections	3452
No. of parameters	201
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.30

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Selected geometric parameters (Å, º) top

Cu1—O1	1.808 (4)	Cu1—N3	1.900 (5)
Cu1—N1	1.843 (5)	Cu1—N2	1.928 (6)

O1—Cu1—N1	93.8 (2)	O1—Cu1—N2	177.3 (2)
O1—Cu1—N3	88.3 (2)	N1—Cu1—N2	87.2 (2)
N1—Cu1—N3	177.8 (2)	N3—Cu1—N2	90.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2'—H2'A···N3ⁱ	0.91	2.35	3.233 (8)	165
N2—H2A···N3ⁱ	0.91	2.35	3.233 (8)	162

Symmetry code: (i) −x, y, −z+1/2.

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