Crystal structures of μ-oxalato-bis­[azido­(hista­mine)­copper(II)] and μ-oxalato-bis­[(dicyan­amido)(hista­mine)­copper(II)]

The title compounds are two closely related oxalate-bridged dinuclear copper complexes. The histamine ligand is in a gauche conformation and coordinates to copper ions in a bidentate chelating fashion. The dinuclear complexes are linked to form three-dimensional networks via different types of hydrogen-bond and weak inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.026
• wR factor = 0.070
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT048_ALERT_1_C MoietyFormula Not Given ........................     Please Do !
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.04 Report
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5     ..  N3      ..       2.69 Ang.
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........         H3
                    C3     H3
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........         H3
                    C3     H3
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........         H3
                    H3     N3
PLAT718_ALERT_1_C D-H..A  Unknown or Inconsistent Label ..........         H3
                    C3     H3     N3
PLAT737_ALERT_1_C D...A   Calc    3.477(3), Rep    3.476(8) ......        2.7 su-Rat
              C3   -N3      1.555   3.646 ............. Bond #         28 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.087 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          2 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT794_ALERT_5_G Tentative Bond Valency for Cu1     (II)    .....       2.18 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          5 Note
PLAT955_ALERT_1_G Reported (CIF) and Actual (FCF) Lmax Differ by .          1 Units

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
  10 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

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




Datablock: II


Alert level B
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          2 Check

Alert level C
PLAT041_ALERT_1_C Calc. and Reported SumFormula    Strings  Differ     Please Check
PLAT241_ALERT_2_C High      Ueq as Compared to Neighbors for .....         N4 Check
PLAT411_ALERT_2_C Short Inter H...H Contact  H6A    ..  H2"A    ..       2.10 Ang.
PLAT707_ALERT_1_C D...A   Calc    3.267(9), Rep  3.2770(10), Dev..       1.11 Sigma
              C2     -O2        1.555   1.556 ............. Bond #         48
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          4 Report

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C16 H18 Cu2 N12 O4
            Atom count from the _atom_site data:  C16. H17.98799 Cu2 N12 O4
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          8 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          8 Report
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          2 Info
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          6 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT045_ALERT_1_G Calculated and Reported Z Differ by ............       2.00 Ratio
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          3 Report
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Cu1    --  N4      ..        7.4 su
PLAT301_ALERT_3_G Main Residue  Disorder ............ Percentage =         12 Note
PLAT432_ALERT_2_G Short Inter X...Y Contact  N4     ..  C2'     ..       2.91 Ang.
PLAT432_ALERT_2_G Short Inter X...Y Contact  C6     ..  C6      ..       3.17 Ang.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          8 Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         55 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         55 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  15 ALERT level G = General information/check it is not something unexpected

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

---

Computing details

For both compounds, data collection: SMART (Bruker, 1998); cell refinement: SMART and SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (I); SHELXS97 (Sheldrick, 2015) for (II). For both compounds, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

(I) µ-Oxalato-κ⁴O¹,O²:O^1',O^2'-bis[[4-(2-aminoethyl)-1H-imidazole-κ²N³,N⁴](azido-κN¹)copper(II)]

Crystal data

[Cu2(C2O4)(N3)2(C5H9N3)2]	Dx = 1.945 Mg m^−3
Mr = 521.46	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 88 reflections
a = 13.4419 (7) Å	θ = 2.0–28.0°
b = 7.4576 (4) Å	µ = 2.44 mm^−1
c = 17.7662 (9) Å	T = 173 K
V = 1780.96 (16) Å^3	Prism, green
Z = 4	0.17 × 0.11 × 0.11 mm
F(000) = 1056

Data collection

Bruker SMART CCD area-detector diffractometer	2027 independent reflections
Radiation source: fine-focus sealed tube	1768 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: integration (SADABS; Bruker, 1998)	h = −13→17
Tmin = 0.682, Tmax = 0.835	k = −9→9
10138 measured reflections	l = −20→23

Refinement

Refinement on F^2	Secondary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.070	w = 1/[σ^2(Fo^2) + (0.0279P)^2 + 1.2918P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.002
2027 reflections	Δρmax = 0.78 e Å^−3
145 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0022 (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.

All H atoms were positioned geometrically (C—H = 0.93/1.00 Å) and allowed to ride with U_iso(H)= 1.2/1.5U_eq(C). Methyl ones were allowed to rotate around the corresponding C—C.

The amino protons were obtained from a Difference Fourier map and refined freely.

A small peak (0.78) was found at 0.3411 0.4069 0.9096, which had the following geometry around it: We believe it is a small trace of a Cu center but was not included in the final refinement model for its small size.

ENVIRONMENT OF Q1

Ligand Symcode Dist. Angles symm operation

O1 6566 2.581 x. 5 - y. 5 + z N1 5656 2.039 107.5 1 - x. 5 + y 1.5 - z N2 5656 2.580 119.2 26.6 1 - x. 5 + y 1.5 - z N3 4557 1.902 108.9 127.6 101.4 -.5 + x y. 5 - z N5 1555 1.928 97.9 94.0 113.7 116.5

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.44296 (2)	0.24198 (3)	0.59064 (2)	0.01472 (11)
O1	0.47496 (11)	0.27517 (17)	0.48108 (7)	0.0173 (3)
O2	0.46843 (11)	0.50801 (17)	0.59516 (7)	0.0181 (3)
N1	0.60261 (13)	0.1548 (2)	0.60977 (10)	0.0221 (4)
N2	0.65931 (13)	0.2515 (2)	0.57879 (9)	0.0182 (3)
N3	0.71372 (14)	0.3492 (3)	0.54767 (10)	0.0301 (4)
N4	0.39863 (12)	0.23846 (19)	0.69487 (9)	0.0159 (3)
N5	0.36694 (12)	0.3189 (2)	0.81078 (9)	0.0199 (3)
H5	0.3614	0.3858	0.8514	0.024*
N6	0.37467 (14)	0.0143 (2)	0.56327 (9)	0.0182 (3)
H6A	0.3427 (19)	0.035 (3)	0.5215 (14)	0.025 (6)*
H6B	0.420 (2)	−0.065 (4)	0.5489 (14)	0.027 (6)*
C1	0.49805 (13)	0.5671 (2)	0.53301 (10)	0.0156 (4)
C2	0.39970 (14)	0.3740 (3)	0.74353 (10)	0.0187 (4)
H2A	0.4207	0.4926	0.7322	0.022*
C3	0.34345 (15)	0.1401 (3)	0.80562 (11)	0.0203 (4)
H3A	0.3182	0.0661	0.8447	0.024*
C4	0.36342 (14)	0.0895 (2)	0.73347 (10)	0.0164 (4)
C5	0.35239 (15)	−0.0881 (2)	0.69514 (11)	0.0187 (4)
H5A	0.3107	−0.1673	0.7268	0.022*
H5B	0.4188	−0.1445	0.6903	0.022*
C6	0.30567 (14)	−0.0729 (3)	0.61751 (11)	0.0188 (4)
H6C	0.2882	−0.1941	0.5990	0.023*
H6D	0.2436	−0.0019	0.6210	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.01840 (16)	0.01299 (14)	0.01277 (15)	−0.00233 (8)	0.00262 (8)	0.00036 (8)
O1	0.0229 (7)	0.0142 (6)	0.0148 (6)	−0.0025 (5)	0.0022 (5)	0.0010 (5)
O2	0.0246 (7)	0.0158 (6)	0.0140 (6)	−0.0019 (5)	0.0021 (5)	0.0016 (5)
N1	0.0205 (9)	0.0218 (8)	0.0240 (8)	0.0025 (7)	0.0006 (7)	0.0050 (7)
N2	0.0192 (8)	0.0197 (8)	0.0156 (7)	0.0012 (6)	−0.0015 (7)	−0.0017 (6)
N3	0.032 (1)	0.0341 (10)	0.0243 (9)	−0.0096 (8)	0.0050 (8)	−0.0009 (8)
N4	0.0156 (8)	0.0166 (8)	0.0155 (8)	−0.0024 (6)	0.0020 (6)	0.0001 (6)
N5	0.0212 (8)	0.0242 (8)	0.0143 (8)	0.0004 (7)	0.0006 (7)	−0.0039 (6)
N6	0.0220 (8)	0.0173 (8)	0.0152 (8)	−0.0018 (7)	0.0017 (7)	−0.0013 (6)
C1	0.0149 (8)	0.0159 (9)	0.0158 (9)	0.0004 (7)	−0.0012 (7)	0.0006 (7)
C2	0.0198 (9)	0.0190 (9)	0.0172 (9)	−0.0007 (7)	−0.0003 (7)	−0.0016 (7)
C3	0.0199 (9)	0.0235 (10)	0.0174 (9)	0.0007 (7)	0.0014 (7)	0.0041 (7)
C4	0.0155 (9)	0.0173 (8)	0.0163 (9)	0.0002 (7)	0.0007 (7)	0.0030 (7)
C5	0.0213 (10)	0.0144 (8)	0.0204 (9)	0.0000 (7)	0.0028 (7)	0.0031 (7)
C6	0.0194 (9)	0.0159 (9)	0.0210 (9)	−0.0037 (7)	0.0022 (8)	−0.0002 (7)

Geometric parameters (Å, º)

Cu1—N4	1.9454 (16)	N6—C6	1.487 (2)
Cu1—N6	1.9904 (17)	N6—H6A	0.87 (3)
Cu1—O1	2.0088 (13)	N6—H6B	0.89 (3)
Cu1—O2	2.0148 (13)	C1—O1^i	1.257 (2)
Cu1—N1	2.2679 (17)	C1—C1^i	1.542 (4)
O1—C1^i	1.257 (2)	C2—H2A	0.9500
O2—C1	1.254 (2)	C3—C4	1.363 (3)
N1—N2	1.185 (2)	C3—H3	0.9500
N2—N3	1.171 (2)	C4—C5	1.497 (3)
N4—C2	1.330 (2)	C5—C6	1.520 (3)
N4—C4	1.388 (2)	C5—H5A	0.9900
N5—C2	1.338 (2)	C5—H5B	0.9900
N5—C3	1.374 (3)	C6—H6C	0.9900
N5—H5	0.8800	C6—H6D	0.9900
N4—Cu1—N6	94.58 (7)	H6A—N6—H6B	102 (2)
N4—Cu1—O1	171.72 (6)	O2—C1—O1^i	126.59 (17)
N6—Cu1—O1	88.11 (6)	O2—C1—C1^i	116.9 (2)
N4—Cu1—O2	91.58 (6)	O1^i—C1—C1^i	116.48 (19)
N6—Cu1—O2	158.12 (7)	N4—C2—N5	110.11 (17)
O1—Cu1—O2	83.16 (5)	N4—C2—H2A	124.9
N4—Cu1—N1	98.24 (6)	N5—C2—H2A	124.9
N6—Cu1—N1	103.21 (7)	C4—C3—N5	106.62 (16)
O1—Cu1—N1	88.73 (6)	C4—C3—H3A	126.7
O2—Cu1—N1	96.63 (6)	N5—C3—H3A	126.7
C1^i—O1—Cu1	111.73 (11)	C3—C4—N4	108.08 (16)
C1—O2—Cu1	111.40 (11)	C3—C4—C5	130.79 (17)
N2—N1—Cu1	111.39 (13)	N4—C4—C5	121.13 (16)
N3—N2—N1	178.6 (2)	C4—C5—C6	112.82 (16)
C2—N4—C4	106.89 (16)	C4—C5—H5A	109.0
C2—N4—Cu1	127.24 (13)	C6—C5—H5A	109.0
C4—N4—Cu1	125.82 (12)	C4—C5—H5B	109.0
C2—N5—C3	108.30 (16)	C6—C5—H5B	109.0
C2—N5—H5	125.8	H5A—C5—H5B	107.8
C3—N5—H5	125.8	N6—C6—C5	111.28 (16)
C6—N6—Cu1	120.15 (12)	N6—C6—H6C	109.4
C6—N6—H6A	108.7 (16)	C5—C6—H6C	109.4
Cu1—N6—H6A	106.6 (16)	N6—C6—H6D	109.4
C6—N6—H6B	108.9 (16)	C5—C6—H6D	109.4
Cu1—N6—H6B	108.7 (17)	H6C—C6—H6D	108.0

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
N5—H5···N1^ii	0.88	2.18	2.904 (2)	140
N5—H5···N3^iii	0.88	2.69	3.258 (2)	124
N6—H6A···N3^iv	0.87 (3)	2.29 (3)	3.099 (3)	154 (2)
N6—H6B···O1^v	0.89 (3)	2.17 (3)	3.061 (2)	175 (2)
C3—H3···N3^vi	0.95	2.54	3.476 (8)	169

Symmetry codes: (ii) −x+1, y+1/2, −z+3/2; (iii) x−1/2, y, −z+3/2; (iv) x−1/2, −y+1/2, −z+1; (v) −x+1, −y, −z+1; (vi) −x+1, y−1/2, −z+3/2.

(II) µ-Oxalato-κ⁴O¹,O²:O^1',O^2'-bis[[4-(2-aminoethyl)-1H-imidazole-κ²N³,N⁴](dicyanamido-κN¹)copper(II)]

Crystal data

[Cu2(C2O4)(C2N3)2(C5H9N3)2]	F(000) = 576
Mr = 569.50	Dx = 1.778 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.6816 (7) Å	Cell parameters from 87 reflections
b = 14.7236 (11) Å	θ = 2.0–28.0°
c = 7.4604 (6) Å	µ = 2.05 mm^−1
β = 90.112 (1)°	T = 173 K
V = 1063.46 (14) Å^3	Plate, blue
Z = 2	0.32 × 0.27 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2374 independent reflections
Radiation source: fine-focus sealed tube	2172 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: analytical (SADABS; Bruker, 1998)	h = −12→10
Tmin = 0.340, Tmax = 0.503	k = −18→18
6331 measured reflections	l = −8→9

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.096	w = 1/[σ^2(Fo^2) + (0.0382P)^2 + 1.0333P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max = 0.001
2374 reflections	Δρmax = 0.34 e Å^−3
198 parameters	Δρmin = −0.42 e Å^−3
55 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.022 (2)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. All H atoms were positioned geometrically (C—H = 0.93/1.00 Å) and allowed to ride with U_iso(H)= 1.2/1.5U_eq(C). Methyl ones were allowed to rotate around the corresponding C—C.

A C2H4 is disordered and was refined in three parts with their site occupation factors adding up to one. As a consequence of this disorder, the two protons on the adjacent N atom are disordered and also were calculated is three idealized positioned and were treated riding on their parent atom. SADI and RIGU were applied to the disorder geometry to maintain equivalent bond lengths of corresponding bonds.

Proton H3 were obtained from a Difference Fourier map and refined freely.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.31334 (3)	0.56430 (2)	0.21722 (4)	0.02660 (15)
O1	0.50672 (18)	0.51395 (14)	0.2322 (2)	0.0288 (4)
O2	0.32980 (18)	0.53232 (14)	−0.0421 (2)	0.0294 (4)
N1	0.3199 (2)	0.58973 (16)	0.4781 (3)	0.0274 (4)
H1A	0.3702	0.5447	0.5303	0.033*	0.516 (3)
H1B	0.3682	0.6422	0.4933	0.033*	0.516 (3)
H1C	0.3102	0.5359	0.5368	0.033*	0.243 (3)
H1D	0.4057	0.6112	0.5044	0.033*	0.243 (3)
H1E	0.3862	0.5547	0.5302	0.033*	0.240 (3)
H1F	0.3426	0.6490	0.4961	0.033*	0.240 (3)
N2	0.1213 (2)	0.60545 (14)	0.1895 (3)	0.0235 (4)
N3	−0.0839 (2)	0.62944 (17)	0.0764 (3)	0.0322 (5)
H3	−0.145 (5)	0.634 (3)	−0.015 (7)	0.073 (14)*
N4	0.4224 (3)	0.7083 (2)	0.1465 (4)	0.0516 (7)
N5	0.6458 (3)	0.7761 (2)	0.0675 (4)	0.0409 (6)
N6	0.7630 (3)	0.89650 (17)	0.2373 (3)	0.0360 (5)
C1	0.5513 (2)	0.49455 (17)	0.0797 (3)	0.0236 (5)
C2	0.1885 (7)	0.5987 (6)	0.5821 (12)	0.0267 (19)	0.516 (3)
H2A	0.2099	0.6155	0.7077	0.032*	0.516 (3)
H2B	0.1392	0.5399	0.5830	0.032*	0.516 (3)
C3	0.0970 (10)	0.6712 (6)	0.4982 (8)	0.0285 (19)	0.516 (3)
H3A	0.0213	0.6867	0.5818	0.034*	0.516 (3)
H3B	0.1520	0.7268	0.4765	0.034*	0.516 (3)
C2'	0.2169 (9)	0.6548 (8)	0.5547 (15)	0.031 (2)	0.243 (3)
H2'A	0.2272	0.7153	0.4985	0.037*	0.243 (3)
H2'B	0.2311	0.6613	0.6856	0.037*	0.243 (3)
C3'	0.0738 (14)	0.6165 (13)	0.5163 (10)	0.033 (4)	0.243 (3)
H3'A	0.0053	0.6442	0.5981	0.039*	0.243 (3)
H3'B	0.0736	0.5500	0.5358	0.039*	0.243 (3)
C2"	0.1832 (11)	0.5704 (13)	0.564 (3)	0.029 (4)	0.240 (3)
H2"A	0.1949	0.5669	0.6956	0.035*	0.240 (3)
H2"B	0.1480	0.5110	0.5214	0.035*	0.240 (3)
C3"	0.079 (3)	0.6445 (17)	0.5181 (13)	0.033 (6)	0.240 (3)
H3"A	0.1213	0.7048	0.5408	0.040*	0.240 (3)
H3"B	−0.0028	0.6384	0.5956	0.040*	0.240 (3)
C4	0.0362 (3)	0.6377 (2)	0.3221 (4)	0.0328 (6)
C5	−0.0920 (3)	0.6523 (2)	0.2523 (4)	0.0332 (6)
H5A	−0.1711	0.6739	0.3143	0.040*
C6	0.0449 (3)	0.6013 (2)	0.0430 (4)	0.0345 (6)
H6A	0.0770	0.5810	−0.0705	0.041*
C7	0.5280 (3)	0.74143 (19)	0.1173 (4)	0.0320 (6)
C8	0.7025 (3)	0.84044 (18)	0.1632 (3)	0.0283 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.01728 (19)	0.0447 (2)	0.01783 (19)	0.00787 (12)	0.00023 (11)	−0.00297 (12)
O1	0.0178 (8)	0.0499 (11)	0.0187 (8)	0.0068 (7)	0.0004 (6)	−0.0011 (8)
O2	0.0172 (8)	0.0505 (11)	0.0204 (8)	0.0075 (7)	0.0008 (6)	−0.0015 (8)
N1	0.0223 (10)	0.0381 (12)	0.0218 (10)	0.0056 (9)	−0.0013 (8)	−0.0024 (9)
N2	0.0189 (9)	0.0293 (11)	0.0222 (10)	0.0040 (8)	0.0009 (7)	−0.0011 (8)
N3	0.0219 (10)	0.0457 (13)	0.0289 (11)	0.0071 (9)	−0.0016 (9)	0.0006 (10)
N4	0.0501 (16)	0.0543 (17)	0.0504 (16)	−0.0225 (14)	0.0002 (13)	0.0072 (14)
N5	0.0345 (12)	0.0526 (15)	0.0356 (13)	−0.0118 (11)	0.0026 (10)	−0.0124 (11)
N6	0.0357 (12)	0.0359 (13)	0.0365 (13)	−0.0036 (10)	−0.0028 (10)	0.0009 (11)
C1	0.0183 (10)	0.0333 (12)	0.0193 (11)	0.0009 (9)	−0.0004 (9)	0.0010 (9)
C2	0.029 (3)	0.030 (5)	0.021 (3)	0.005 (2)	0.007 (2)	−0.002 (3)
C3	0.031 (3)	0.028 (4)	0.027 (3)	0.010 (3)	0.001 (2)	−0.004 (2)
C2'	0.028 (4)	0.039 (6)	0.025 (5)	0.006 (4)	−0.001 (4)	−0.008 (4)
C3'	0.025 (5)	0.052 (10)	0.022 (5)	0.005 (5)	0.005 (4)	−0.013 (5)
C2"	0.031 (5)	0.044 (10)	0.012 (5)	0.011 (5)	0.000 (4)	−0.007 (6)
C3"	0.033 (8)	0.041 (14)	0.027 (6)	0.008 (7)	−0.004 (5)	−0.018 (5)
C4	0.0243 (12)	0.0475 (16)	0.0265 (12)	0.0116 (11)	0.0012 (10)	−0.0070 (11)
C5	0.0218 (12)	0.0462 (16)	0.0315 (13)	0.0110 (11)	0.0019 (10)	−0.0003 (12)
C6	0.0244 (12)	0.0556 (17)	0.0236 (12)	0.0098 (12)	−0.0021 (10)	−0.0032 (12)
C7	0.0346 (14)	0.0300 (13)	0.0315 (13)	0.0002 (11)	−0.0052 (11)	0.0028 (11)
C8	0.0248 (12)	0.0339 (13)	0.0261 (12)	0.0035 (10)	0.0008 (10)	0.0038 (10)

Geometric parameters (Å, º)

Cu1—N2	1.966 (2)	N6—C8	1.153 (4)
Cu1—N1	1.983 (2)	C1—O2^i	1.249 (3)
Cu1—O2	1.9978 (18)	C1—C1^i	1.557 (4)
Cu1—O1	2.0165 (17)	C2—C3	1.521 (7)
Cu1—N4	2.426 (3)	C2—H2A	0.9900
O1—C1	1.251 (3)	C2—H2B	0.9900
O2—C1^i	1.249 (3)	C3—C4	1.521 (5)
N1—C2	1.497 (5)	C3—H3A	0.9900
N1—C2'	1.497 (6)	C3—H3B	0.9900
N1—C2"	1.498 (6)	C2'—C3'	1.522 (8)
N1—H1A	0.9100	C2'—H2'A	0.9900
N1—H1B	0.9100	C2'—H2'B	0.9900
N1—H1C	0.9100	C3'—C4	1.526 (6)
N1—H1D	0.9100	C3'—H3'A	0.9900
N1—H1E	0.9100	C3'—H3'B	0.9900
N1—H1F	0.9100	C2"—C3"	1.521 (8)
N2—C6	1.320 (3)	C2"—H2"A	0.9900
N2—C4	1.373 (3)	C2"—H2"B	0.9900
N3—C6	1.338 (3)	C3"—C4	1.524 (6)
N3—C5	1.357 (4)	C3"—H3"A	0.9900
N3—H3	0.91 (5)	C3"—H3"B	0.9900
N4—C7	1.154 (4)	C4—C5	1.362 (4)
N5—C7	1.304 (4)	C5—H5A	0.9500
N5—C8	1.306 (4)	C6—H6A	0.9500
N2—Cu1—N1	94.21 (9)	H2A—C2—H2B	108.2
N2—Cu1—O2	92.75 (8)	C4—C3—C2	110.7 (7)
N1—Cu1—O2	173.01 (8)	C4—C3—H3A	109.5
N2—Cu1—O1	175.44 (8)	C2—C3—H3A	109.5
N1—Cu1—O1	89.27 (8)	C4—C3—H3B	109.5
O2—Cu1—O1	83.74 (7)	C2—C3—H3B	109.5
N2—Cu1—N4	96.87 (10)	H3A—C3—H3B	108.1
N1—Cu1—N4	92.03 (10)	N1—C2'—C3'	107.3 (9)
O2—Cu1—N4	87.70 (10)	N1—C2'—H2'A	110.3
O1—Cu1—N4	85.92 (10)	C3'—C2'—H2'A	110.3
C1—O1—Cu1	110.86 (15)	N1—C2'—H2'B	110.3
C1^i—O2—Cu1	111.54 (15)	C3'—C2'—H2'B	110.3
C2—N1—Cu1	120.0 (4)	H2'A—C2'—H2'B	108.5
C2'—N1—Cu1	118.4 (4)	C2'—C3'—C4	108.6 (8)
C2"—N1—Cu1	110.9 (8)	C2'—C3'—H3'A	110.0
C2—N1—H1A	107.3	C4—C3'—H3'A	110.0
Cu1—N1—H1A	107.3	C2'—C3'—H3'B	110.0
C2—N1—H1B	107.3	C4—C3'—H3'B	110.0
Cu1—N1—H1B	107.3	H3'A—C3'—H3'B	108.4
H1A—N1—H1B	106.9	N1—C2"—C3"	110.5 (17)
C2'—N1—H1C	107.7	N1—C2"—H2"A	109.5
Cu1—N1—H1C	107.7	C3"—C2"—H2"A	109.5
C2'—N1—H1D	107.7	N1—C2"—H2"B	109.5
Cu1—N1—H1D	107.7	C3"—C2"—H2"B	109.5
H1C—N1—H1D	107.1	H2"A—C2"—H2"B	108.1
C2"—N1—H1E	109.5	C2"—C3"—C4	110.4 (15)
Cu1—N1—H1E	109.5	C2"—C3"—H3"A	109.6
C2"—N1—H1F	109.5	C4—C3"—H3"A	109.6
Cu1—N1—H1F	109.5	C2"—C3"—H3"B	109.6
H1E—N1—H1F	108.0	C4—C3"—H3"B	109.6
C6—N2—C4	106.1 (2)	H3"A—C3"—H3"B	108.1
C6—N2—Cu1	126.94 (18)	C5—C4—N2	109.1 (2)
C4—N2—Cu1	126.83 (17)	C5—C4—C3	129.0 (4)
C6—N3—C5	108.2 (2)	N2—C4—C3	120.2 (4)
C6—N3—H3	120 (3)	C5—C4—C3"	127.2 (10)
C5—N3—H3	132 (3)	N2—C4—C3"	123.3 (10)
C7—N4—Cu1	142.8 (3)	C5—C4—C3'	127.6 (6)
C7—N5—C8	119.7 (3)	N2—C4—C3'	118.1 (7)
O2^i—C1—O1	126.6 (2)	N3—C5—C4	106.0 (2)
O2^i—C1—C1^i	116.7 (3)	N3—C5—H5A	127.0
O1—C1—C1^i	116.7 (3)	C4—C5—H5A	127.0
N1—C2—C3	110.1 (7)	N2—C6—N3	110.6 (2)
N1—C2—H2A	109.6	N2—C6—H6A	124.7
C3—C2—H2A	109.6	N3—C6—H6A	124.7
N1—C2—H2B	109.6	N4—C7—N5	174.2 (3)
C3—C2—H2B	109.6	N6—C8—N5	173.6 (3)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1E···O1^ii	0.91	2.29	3.131 (3)	154
N1—H1F···N4^iii	0.91	2.50	3.377 (4)	161
N3—H3···N6^iv	0.91 (5)	2.10 (5)	2.954 (3)	157 (4)
C2—H2A···O2^v	0.99	2.52	3.277 (1)	133

Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) x, −y+3/2, z+1/2; (iv) x−1, −y+3/2, z−1/2; (v) x, y, z+1.