{2-[(5-Bromo-2-oxidobenzyl­idene)amino-κ2N,O]-3-methyl­penta­noato-κO}(1,10-phenanthroline-κ2N,N′)copper(II) dihydrate

Liu, Z.; Wang, Y.-L.; Wang, Y.

doi:10.1107/S1600536808009495

{2-[(5-Bromo-2-oxidobenzylidene)amino-κ²N,O]-3-methylpentanoato-κO}(1,10-phenanthroline-κ²N,N′)copper(II) dihydrate

In the title compound, [Cu(C₁₃H₁₄BrNO₃)(C₁₂H₈N₂)]·2H₂O, the Cu^II atom is pentacoordinated in a square-pyramidal geometry. The crystal packing is stabilized by O—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808009495/bt2691sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808009495/bt2691Isup2.hkl Contains datablock I

CCDC reference: 690811

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.012 Å
R factor = 0.055
wR factor = 0.075
Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H27    ..  H29     ..       2.08 Ang.

Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.65 mm
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.02 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.31 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C15
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C25
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         12
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          3
            N2  -CU1 -N1  -C7    139.00  5.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          7
            N2  -CU1 -N1  -C2    -26.00  5.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         10
            N1  -CU1 -N2  -C14    91.00  5.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         14
            N1  -CU1 -N2  -C18   -94.00  5.00   1.555   1.555   1.555   1.555

Alert level G
REFLT03_ALERT_4_G 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.
           From the CIF: _diffrn_reflns_theta_max           25.01
           From the CIF: _reflns_number_total               4255
           Count of symmetry unique reflns         2470
           Completeness (_total/calc)            172.27%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1785
           Fraction of Friedel pairs measured     0.723
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2     ...          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     ...          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Schiff base complexes play an important role in antibacterial and catalytic performance, and have attracted widespread interest by researchers (Jiang et al., 2003; Kettmann et al., 1993; Zhang, 2006). Meanwhile, Schiff base complexes containing isoleucine have been studied because they are of great significance in the biological and medical field (Royles et al., 2000; Feng et al., 2007; Li et al., 2006).

The central Cu^II atom is penta-coordinated (Fig.1). The quadratic planar is composed by O1, N2, O3and N1. The Schiff base forms two chelating rings(O1—C1—C2—N1—Cu1 and N1—C7—C8—C9—O3- Cu1) to the Cu^IIatom, with a diheral angle of 19.6 (4)° which is in the range observed for many copper Schiff base complexes. The N3 atom occupies the axial position with a N—Cu length of 2.229 (6) Å, comparing with the equatorial Cu—N bond lengths [Cu1—N1 1.924 (6)Å and N2—Cu1 1.975 (6)Å]. The crystal packing is stabilized by O—H···O hydrogen bonds (Fig. 2).

Related literature top

For related literature, see: Feng et al. (2007); Li et al. (2006); Royles & Sherrington (2000); Jiang et al. (2003); Kettmann et al. (1993); Zhang (2006); Zhang et al. (2003).

Experimental top

5-Bromo-2-hydroxy-benzaldehyde(0.5 mmol, 100.5 mg) was dissolved in hot ethanol(5 ml), then a mixture of D,L-isoleucine (0.5 mmol, 65.6 mg) and sodium hydroxide (1.0 mmol, 40 mg) was added. After stirring for 1 h, the copper dinitrate trihydrate(0.5 mmol, 120.8 mg) was added and refluxed for another 2 h. At last, an ethanol solution of Phen(0.5 mmol, 99.1 mg) was dropped gradually into to the reaction mixture and refluxed for further 3 h (Zhang et al., 2003; Zhang et al., 2006). The obtained green solution was filtered and held at room temperature for ten days, whereupon green crystals suitable for X-ray diffraction were obtained (yield: 45.2%, based on Cu).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SMART (Bruker, 2004); data reduction: SAINT (Bruker, 2004) and SHELXTL (Sheldrick, 2008); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound.

{2-[(5-Bromo-2-oxidobenzylidene)amino-κ²N,O]-3-methylpentanoato-κO}(1,10- phenanthroline-κ²N,N')copper(II) top

Crystal data top

[Cu(C₁₃H₁₄BrNO₃)(C₁₂H₈N₂)]·2H₂O	F(000) = 602
M_r = 591.94	D_x = 1.550 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 10.6184 (18) Å	Cell parameters from 1263 reflections
b = 6.0520 (16) Å	θ = 2.2–18.0°
c = 19.777 (3) Å	µ = 2.48 mm⁻¹
β = 93.481 (2)°	T = 298 K
V = 1268.5 (4) Å³	Block, green
Z = 2	0.65 × 0.10 × 0.07 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4255 independent reflections
Radiation source: fine-focus sealed tube	2269 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→10
T_min = 0.296, T_max = 0.846	k = −7→7
6692 measured reflections	l = −23→21

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.074	w = 1/[σ²(F_o²) + (0.0003P)²] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max = 0.001
4255 reflections	Δρ_max = 0.52 e Å⁻³
318 parameters	Δρ_min = −0.26 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1785 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.054 (14)

Crystal data top

[Cu(C₁₃H₁₄BrNO₃)(C₁₂H₈N₂)]·2H₂O	V = 1268.5 (4) Å³
M_r = 591.94	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.6184 (18) Å	µ = 2.48 mm⁻¹
b = 6.0520 (16) Å	T = 298 K
c = 19.777 (3) Å	0.65 × 0.10 × 0.07 mm
β = 93.481 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4255 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2269 reflections with I > 2σ(I)
T_min = 0.296, T_max = 0.846	R_int = 0.053
6692 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.074	Δρ_max = 0.52 e Å⁻³
S = 0.96	Δρ_min = −0.26 e Å⁻³
4255 reflections	Absolute structure: Flack (1983), 1785 Friedel pairs
318 parameters	Absolute structure parameter: 0.054 (14)
1 restraint

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
Cu1	0.13990 (7)	0.36558 (17)	0.76571 (4)	0.0503 (3)
Br1	−0.25268 (7)	0.10824 (17)	0.46920 (4)	0.0793 (3)
N1	0.2064 (5)	0.1850 (11)	0.6962 (3)	0.0440 (18)
N2	0.0762 (6)	0.5406 (11)	0.8407 (3)	0.052 (2)
N3	−0.0327 (5)	0.1749 (11)	0.7873 (3)	0.0451 (18)
O1	0.2695 (4)	0.2179 (10)	0.8245 (2)	0.0594 (17)
O2	0.4200 (4)	−0.0388 (10)	0.8229 (2)	0.077 (2)
O3	0.0499 (4)	0.5429 (9)	0.6982 (2)	0.0540 (17)
O4	0.4374 (5)	0.7917 (11)	0.9519 (3)	0.115 (3)
H26	0.5106	0.7840	0.9717	0.172*
H27	0.4480	0.7869	0.9097	0.172*
O5	0.3458 (5)	0.3755 (14)	0.9595 (3)	0.124 (2)
H28	0.3213	0.3217	0.9213	0.186*
H29	0.3693	0.5068	0.9516	0.186*
C1	0.3385 (7)	0.0792 (17)	0.7944 (4)	0.057 (2)
C2	0.3235 (5)	0.0722 (14)	0.7175 (3)	0.050 (2)
H2	0.3166	−0.0826	0.7032	0.060*
C3	0.4394 (6)	0.1737 (12)	0.6871 (3)	0.056 (2)
H3	0.5136	0.1047	0.7101	0.067*
C4	0.4473 (6)	0.4206 (12)	0.7027 (4)	0.068 (3)
H4A	0.3766	0.4937	0.6787	0.082*
H4B	0.4380	0.4410	0.7508	0.082*
C5	0.5670 (7)	0.5334 (16)	0.6844 (5)	0.130 (5)
H5A	0.6384	0.4473	0.7009	0.195*
H5B	0.5715	0.6776	0.7046	0.195*
H5C	0.5674	0.5471	0.6361	0.195*
C6	0.4453 (6)	0.1239 (17)	0.6124 (3)	0.080 (3)
H6A	0.3874	0.2180	0.5868	0.121*
H6B	0.4229	−0.0278	0.6041	0.121*
H6C	0.5294	0.1498	0.5989	0.121*
C7	0.1408 (6)	0.1318 (15)	0.6429 (3)	0.050 (2)
H7	0.1678	0.0130	0.6178	0.060*
C8	0.0288 (7)	0.2422 (14)	0.6194 (3)	0.043 (2)
C9	−0.0084 (7)	0.4464 (14)	0.6466 (4)	0.043 (2)
C10	−0.1150 (6)	0.5530 (14)	0.6133 (3)	0.055 (3)
H10	−0.1375	0.6935	0.6273	0.066*
C11	−0.1843 (7)	0.4556 (15)	0.5618 (4)	0.054 (2)
H11	−0.2544	0.5280	0.5418	0.065*
C12	−0.1509 (7)	0.2463 (16)	0.5385 (4)	0.049 (3)
C13	−0.0444 (6)	0.1447 (15)	0.5654 (3)	0.049 (2)
H13	−0.0199	0.0097	0.5480	0.059*
C14	0.1304 (8)	0.7140 (15)	0.8709 (4)	0.065 (3)
H14	0.2111	0.7518	0.8592	0.078*
C15	0.0755 (11)	0.843 (2)	0.9188 (4)	0.090 (3)
H15	0.1181	0.9647	0.9378	0.108*
C16	−0.0422 (10)	0.7901 (18)	0.9377 (4)	0.084 (4)
H16	−0.0805	0.8744	0.9700	0.101*
C17	−0.1043 (9)	0.610 (2)	0.9084 (4)	0.069 (3)
C18	−0.0414 (8)	0.4876 (14)	0.8610 (4)	0.048 (2)
C19	−0.1002 (7)	0.2918 (15)	0.8301 (4)	0.050 (2)
C20	−0.2215 (8)	0.2353 (18)	0.8491 (4)	0.062 (3)
C21	−0.2734 (8)	0.042 (2)	0.8195 (5)	0.083 (4)
H21	−0.3541	−0.0035	0.8289	0.100*
C22	−0.2037 (8)	−0.0789 (18)	0.7768 (4)	0.082 (4)
H22	−0.2362	−0.2084	0.7573	0.098*
C23	−0.0860 (8)	−0.0077 (15)	0.7629 (4)	0.063 (3)
H23	−0.0402	−0.0941	0.7343	0.075*
C24	−0.2293 (10)	0.536 (2)	0.9246 (5)	0.090 (4)
H24	−0.2725	0.6154	0.9562	0.108*
C25	−0.2840 (9)	0.359 (3)	0.8958 (5)	0.094 (4)
H25	−0.3645	0.3182	0.9069	0.113*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0480 (5)	0.0569 (7)	0.0457 (6)	−0.0033 (6)	0.0014 (4)	−0.0045 (6)
Br1	0.0785 (6)	0.0890 (9)	0.0672 (6)	−0.0008 (6)	−0.0220 (5)	−0.0151 (7)
N1	0.034 (4)	0.058 (5)	0.040 (4)	−0.009 (3)	0.003 (3)	0.012 (3)
N2	0.056 (5)	0.051 (6)	0.047 (4)	−0.002 (4)	−0.006 (3)	−0.006 (4)
N3	0.053 (4)	0.044 (5)	0.038 (4)	0.008 (4)	0.003 (3)	0.001 (3)
O1	0.053 (3)	0.082 (5)	0.044 (3)	0.005 (3)	0.004 (3)	0.000 (3)
O2	0.058 (3)	0.112 (6)	0.061 (4)	0.019 (3)	0.002 (3)	0.028 (4)
O3	0.062 (3)	0.057 (5)	0.041 (3)	0.000 (3)	−0.010 (2)	−0.010 (3)
O4	0.124 (5)	0.134 (8)	0.083 (5)	−0.028 (5)	−0.019 (4)	0.026 (5)
O5	0.188 (6)	0.110 (6)	0.070 (4)	−0.040 (6)	−0.032 (4)	0.021 (5)
C1	0.050 (6)	0.064 (7)	0.056 (6)	−0.006 (5)	−0.001 (4)	0.013 (6)
C2	0.038 (4)	0.050 (6)	0.061 (5)	−0.006 (4)	−0.005 (4)	0.005 (5)
C3	0.052 (5)	0.063 (8)	0.053 (5)	0.011 (5)	0.007 (4)	0.001 (5)
C4	0.053 (5)	0.064 (9)	0.088 (7)	−0.019 (5)	0.004 (4)	0.011 (6)
C5	0.089 (7)	0.105 (12)	0.195 (12)	−0.034 (8)	0.005 (7)	0.011 (9)
C6	0.077 (5)	0.101 (9)	0.064 (6)	−0.001 (7)	0.003 (4)	−0.004 (7)
C7	0.050 (5)	0.056 (6)	0.046 (5)	0.000 (5)	0.006 (4)	−0.005 (5)
C8	0.046 (5)	0.055 (7)	0.027 (5)	0.000 (4)	0.005 (4)	0.000 (4)
C9	0.052 (5)	0.045 (7)	0.033 (5)	0.006 (4)	0.008 (4)	−0.002 (4)
C10	0.076 (6)	0.047 (7)	0.042 (5)	0.016 (5)	0.000 (4)	−0.009 (5)
C11	0.063 (6)	0.049 (7)	0.047 (6)	0.018 (5)	−0.009 (4)	0.000 (5)
C12	0.044 (5)	0.069 (8)	0.035 (5)	0.000 (5)	0.001 (4)	0.004 (5)
C13	0.065 (5)	0.043 (6)	0.040 (5)	0.001 (5)	0.008 (4)	−0.003 (5)
C14	0.084 (7)	0.051 (7)	0.057 (6)	−0.004 (6)	−0.011 (5)	0.006 (5)
C15	0.177 (10)	0.058 (7)	0.033 (5)	0.006 (10)	−0.008 (6)	−0.009 (6)
C16	0.132 (9)	0.074 (10)	0.046 (6)	0.041 (8)	0.014 (6)	−0.004 (6)
C17	0.095 (7)	0.079 (8)	0.032 (5)	0.018 (8)	0.000 (5)	−0.005 (6)
C18	0.059 (6)	0.056 (6)	0.030 (5)	0.014 (5)	−0.002 (4)	0.002 (4)
C19	0.047 (5)	0.062 (8)	0.040 (5)	−0.004 (5)	−0.004 (4)	0.017 (5)
C20	0.052 (6)	0.079 (8)	0.055 (7)	−0.003 (6)	0.001 (5)	0.014 (6)
C21	0.048 (6)	0.120 (13)	0.081 (8)	−0.009 (7)	−0.010 (5)	0.041 (8)
C22	0.060 (6)	0.105 (11)	0.076 (7)	−0.040 (7)	−0.030 (5)	0.024 (7)
C23	0.073 (7)	0.046 (7)	0.067 (6)	−0.015 (5)	−0.018 (5)	−0.007 (5)
C24	0.089 (9)	0.131 (14)	0.052 (7)	0.048 (8)	0.030 (6)	0.027 (7)
C25	0.070 (7)	0.143 (12)	0.072 (8)	0.027 (10)	0.020 (6)	0.026 (9)

Geometric parameters (Å, º) top

Cu1—O3	1.922 (5)	C6—H6C	0.9600
Cu1—N1	1.924 (6)	C7—C8	1.417 (9)
Cu1—O1	1.963 (5)	C7—H7	0.9300
Cu1—N2	1.975 (6)	C8—C13	1.411 (9)
Cu1—N3	2.229 (6)	C8—C9	1.413 (9)
Br1—C12	1.888 (8)	C9—C10	1.429 (9)
N1—C7	1.269 (7)	C10—C11	1.355 (9)
N1—C2	1.458 (7)	C10—H10	0.9300
N2—C14	1.322 (9)	C11—C12	1.401 (10)
N2—C18	1.373 (8)	C11—H11	0.9300
N3—C23	1.320 (9)	C12—C13	1.367 (9)
N3—C19	1.343 (9)	C13—H13	0.9300
O1—C1	1.284 (9)	C14—C15	1.385 (11)
O2—C1	1.232 (8)	C14—H14	0.9300
O3—C9	1.300 (8)	C15—C16	1.365 (11)
O4—H26	0.8500	C15—H15	0.9300
O4—H27	0.8500	C16—C17	1.384 (13)
O5—H28	0.8501	C16—H16	0.9300
O5—H29	0.8500	C17—C18	1.396 (11)
C1—C2	1.520 (6)	C17—C24	1.454 (12)
C2—C3	1.531 (6)	C18—C19	1.456 (10)
C2—H2	0.9800	C19—C20	1.405 (10)
C3—C6	1.512 (6)	C20—C25	1.389 (12)
C3—C4	1.528 (6)	C20—C21	1.406 (12)
C3—H3	0.9800	C21—C22	1.368 (11)
C4—C5	1.506 (6)	C21—H21	0.9300
C4—H4A	0.9700	C22—C23	1.365 (9)
C4—H4B	0.9700	C22—H22	0.9300
C5—H5A	0.9600	C23—H23	0.9300
C5—H5B	0.9600	C24—C25	1.330 (14)
C5—H5C	0.9600	C24—H24	0.9300
C6—H6A	0.9600	C25—H25	0.9300
C6—H6B	0.9600

O3—Cu1—N1	90.5 (2)	N1—C7—H7	118.0
O3—Cu1—O1	165.3 (2)	C8—C7—H7	118.0
N1—Cu1—O1	83.7 (2)	C13—C8—C9	120.0 (7)
O3—Cu1—N2	92.5 (2)	C13—C8—C7	117.6 (8)
N1—Cu1—N2	177.0 (3)	C9—C8—C7	122.4 (7)
O1—Cu1—N2	93.4 (2)	O3—C9—C8	124.1 (7)
O3—Cu1—N3	92.42 (19)	O3—C9—C10	119.0 (8)
N1—Cu1—N3	100.6 (2)	C8—C9—C10	116.9 (7)
O1—Cu1—N3	101.9 (2)	C11—C10—C9	121.9 (8)
N2—Cu1—N3	79.1 (3)	C11—C10—H10	119.0
C7—N1—C2	122.5 (7)	C9—C10—H10	119.0
C7—N1—Cu1	122.0 (5)	C10—C11—C12	120.2 (8)
C2—N1—Cu1	113.8 (4)	C10—C11—H11	119.9
C14—N2—C18	115.6 (7)	C12—C11—H11	119.9
C14—N2—Cu1	127.3 (7)	C13—C12—C11	120.0 (8)
C18—N2—Cu1	116.9 (6)	C13—C12—Br1	120.5 (7)
C23—N3—C19	115.9 (7)	C11—C12—Br1	119.5 (7)
C23—N3—Cu1	134.7 (6)	C12—C13—C8	120.8 (8)
C19—N3—Cu1	109.0 (5)	C12—C13—H13	119.6
C1—O1—Cu1	115.0 (5)	C8—C13—H13	119.6
C9—O3—Cu1	119.2 (5)	N2—C14—C15	124.6 (9)
H26—O4—H27	106.2	N2—C14—H14	117.7
H28—O5—H29	105.7	C15—C14—H14	117.7
O2—C1—O1	124.8 (7)	C16—C15—C14	119.0 (11)
O2—C1—C2	118.0 (8)	C16—C15—H15	120.5
O1—C1—C2	117.0 (7)	C14—C15—H15	120.5
N1—C2—C1	108.2 (6)	C15—C16—C17	119.6 (10)
N1—C2—C3	112.9 (6)	C15—C16—H16	120.2
C1—C2—C3	110.1 (6)	C17—C16—H16	120.2
N1—C2—H2	108.5	C16—C17—C18	117.6 (10)
C1—C2—H2	108.5	C16—C17—C24	124.6 (11)
C3—C2—H2	108.5	C18—C17—C24	117.8 (11)
C6—C3—C4	112.8 (7)	N2—C18—C17	123.7 (9)
C6—C3—C2	112.7 (6)	N2—C18—C19	116.3 (8)
C4—C3—C2	110.4 (6)	C17—C18—C19	120.1 (9)
C6—C3—H3	106.8	N3—C19—C20	125.0 (9)
C4—C3—H3	106.8	N3—C19—C18	117.4 (7)
C2—C3—H3	106.8	C20—C19—C18	117.6 (9)
C5—C4—C3	115.6 (7)	C25—C20—C19	121.9 (10)
C5—C4—H4A	108.4	C25—C20—C21	122.3 (11)
C3—C4—H4A	108.4	C19—C20—C21	115.7 (9)
C5—C4—H4B	108.4	C22—C21—C20	119.2 (10)
C3—C4—H4B	108.4	C22—C21—H21	120.4
H4A—C4—H4B	107.4	C20—C21—H21	120.4
C4—C5—H5A	109.5	C23—C22—C21	119.4 (10)
C4—C5—H5B	109.5	C23—C22—H22	120.3
H5A—C5—H5B	109.5	C21—C22—H22	120.3
C4—C5—H5C	109.5	N3—C23—C22	124.7 (9)
H5A—C5—H5C	109.5	N3—C23—H23	117.7
H5B—C5—H5C	109.5	C22—C23—H23	117.7
C3—C6—H6A	109.5	C25—C24—C17	122.2 (11)
C3—C6—H6B	109.5	C25—C24—H24	118.9
H6A—C6—H6B	109.5	C17—C24—H24	118.9
C3—C6—H6C	109.5	C24—C25—C20	120.4 (11)
H6A—C6—H6C	109.5	C24—C25—H25	119.8
H6B—C6—H6C	109.5	C20—C25—H25	119.8
N1—C7—C8	124.1 (8)

O3—Cu1—N1—C7	−38.3 (6)	Cu1—O3—C9—C8	−28.3 (9)
O1—Cu1—N1—C7	155.2 (6)	Cu1—O3—C9—C10	153.4 (5)
N2—Cu1—N1—C7	139 (5)	C13—C8—C9—O3	176.7 (7)
N3—Cu1—N1—C7	54.2 (7)	C7—C8—C9—O3	−5.4 (11)
O3—Cu1—N1—C2	156.3 (5)	C13—C8—C9—C10	−5.0 (10)
O1—Cu1—N1—C2	−10.2 (5)	C7—C8—C9—C10	172.9 (7)
N2—Cu1—N1—C2	−26 (5)	O3—C9—C10—C11	−176.1 (7)
N3—Cu1—N1—C2	−111.1 (5)	C8—C9—C10—C11	5.6 (11)
O3—Cu1—N2—C14	−92.1 (6)	C9—C10—C11—C12	−1.4 (12)
N1—Cu1—N2—C14	91 (5)	C10—C11—C12—C13	−3.4 (11)
O1—Cu1—N2—C14	74.5 (6)	C10—C11—C12—Br1	177.4 (6)
N3—Cu1—N2—C14	175.9 (6)	C11—C12—C13—C8	3.8 (11)
O3—Cu1—N2—C18	83.0 (5)	Br1—C12—C13—C8	−177.0 (5)
N1—Cu1—N2—C18	−94 (5)	C9—C8—C13—C12	0.5 (10)
O1—Cu1—N2—C18	−110.5 (5)	C7—C8—C13—C12	−177.5 (6)
N3—Cu1—N2—C18	−9.0 (5)	C18—N2—C14—C15	−1.7 (11)
O3—Cu1—N3—C23	90.0 (7)	Cu1—N2—C14—C15	173.4 (7)
N1—Cu1—N3—C23	−1.0 (7)	N2—C14—C15—C16	0.9 (14)
O1—Cu1—N3—C23	−86.7 (7)	C14—C15—C16—C17	−0.4 (14)
N2—Cu1—N3—C23	−177.9 (7)	C15—C16—C17—C18	0.9 (14)
O3—Cu1—N3—C19	−82.0 (5)	C15—C16—C17—C24	179.7 (9)
N1—Cu1—N3—C19	−173.0 (5)	C14—N2—C18—C17	2.3 (11)
O1—Cu1—N3—C19	101.3 (5)	Cu1—N2—C18—C17	−173.4 (6)
N2—Cu1—N3—C19	10.1 (5)	C14—N2—C18—C19	−177.6 (6)
O3—Cu1—O1—C1	−66.4 (12)	Cu1—N2—C18—C19	6.7 (8)
N1—Cu1—O1—C1	1.0 (6)	C16—C17—C18—N2	−1.9 (13)
N2—Cu1—O1—C1	−179.9 (6)	C24—C17—C18—N2	179.3 (8)
N3—Cu1—O1—C1	100.6 (6)	C16—C17—C18—C19	178.0 (7)
N1—Cu1—O3—C9	42.5 (5)	C24—C17—C18—C19	−0.8 (12)
O1—Cu1—O3—C9	109.1 (10)	C23—N3—C19—C20	−1.1 (11)
N2—Cu1—O3—C9	−137.3 (5)	Cu1—N3—C19—C20	172.5 (6)
N3—Cu1—O3—C9	−58.1 (5)	C23—N3—C19—C18	176.6 (6)
Cu1—O1—C1—O2	−175.7 (7)	Cu1—N3—C19—C18	−9.7 (7)
Cu1—O1—C1—C2	8.3 (9)	N2—C18—C19—N3	3.1 (9)
C7—N1—C2—C1	−149.3 (7)	C17—C18—C19—N3	−176.8 (7)
Cu1—N1—C2—C1	16.0 (7)	N2—C18—C19—C20	−179.0 (7)
C7—N1—C2—C3	88.5 (8)	C17—C18—C19—C20	1.1 (11)
Cu1—N1—C2—C3	−106.2 (5)	N3—C19—C20—C25	177.4 (8)
O2—C1—C2—N1	167.9 (7)	C18—C19—C20—C25	−0.3 (12)
O1—C1—C2—N1	−15.8 (10)	N3—C19—C20—C21	−0.6 (11)
O2—C1—C2—C3	−68.2 (10)	C18—C19—C20—C21	−178.3 (7)
O1—C1—C2—C3	108.0 (8)	C25—C20—C21—C22	−176.4 (9)
N1—C2—C3—C6	−72.6 (8)	C19—C20—C21—C22	1.6 (12)
C1—C2—C3—C6	166.3 (8)	C20—C21—C22—C23	−0.9 (14)
N1—C2—C3—C4	54.6 (8)	C19—N3—C23—C22	2.0 (11)
C1—C2—C3—C4	−66.5 (9)	Cu1—N3—C23—C22	−169.6 (6)
C6—C3—C4—C5	−61.5 (9)	C21—C22—C23—N3	−1.0 (13)
C2—C3—C4—C5	171.4 (6)	C16—C17—C24—C25	−178.9 (11)
C2—N1—C7—C8	−177.8 (6)	C18—C17—C24—C25	−0.1 (15)
Cu1—N1—C7—C8	18.1 (10)	C17—C24—C25—C20	0.9 (18)
N1—C7—C8—C13	−170.6 (7)	C19—C20—C25—C24	−0.6 (17)
N1—C7—C8—C9	11.5 (11)	C21—C20—C25—C24	177.2 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H28···O1	0.85	2.06	2.904 (8)	174
O5—H29···O4	0.85	1.87	2.708 (10)	168
O4—H26···O5ⁱ	0.85	2.06	2.853 (8)	156
O4—H27···O2ⁱⁱ	0.85	2.02	2.746 (7)	143

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

Experimental details

Crystal data
Chemical formula	[Cu(C₁₃H₁₄BrNO₃)(C₁₂H₈N₂)]·2H₂O
M_r	591.94
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	10.6184 (18), 6.0520 (16), 19.777 (3)
β (°)	93.481 (2)
V (Å³)	1268.5 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.48
Crystal size (mm)	0.65 × 0.10 × 0.07

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.296, 0.846
No. of measured, independent and observed [I > 2σ(I)] reflections	6692, 4255, 2269
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.074, 0.96
No. of reflections	4255
No. of parameters	318
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.26
Absolute structure	Flack (1983), 1785 Friedel pairs
Absolute structure parameter	0.054 (14)

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004) and SHELXTL (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).