trans-Bis(N-{2-[2-(3-methyl-1H-pyrazol-5-yl-κN2)acetamido-κO]­phen­yl}benzamide)bis(per­chlor­ato-κO)copper(II)

Chkirate, K.; Sebbar, N.K.; Ouzidan, Y.; Essassi, E.M.; Mague, J.T.

doi:10.1107/S2414314617002851

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 2| February 2017| x170285

https://doi.org/10.1107/S2414314617002851

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trans-Bis(N-{2-[2-(3-methyl-1H-pyrazol-5-yl-κN²)acetamido-κO]phenyl}benzamide)bis(perchlorato-κO)copper(II)

Karim Chkirate,^a ^* Nada Kheira Sebbar,^a Younes Ouzidan,^b El Mokhtar Essassi ^a and Joel T. Mague ^c

^aLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, ^bLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Imouzzer, BP 2202, Fez, Morocco, and ^cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: chkiratekarim@gmail.com

Edited by O. Blacque, University of Zürich, Switzerland (Received 12 February 2017; accepted 20 February 2017; online 28 February 2017)

In the centrosymmetric title compound, [Cu(C₁₉H₁₈N₄O₂)₂(ClO₄)₂], the copper ion sits at the center of an axially elongated octahedron with monodentate perchlorate ions weakly coordinated in the axial positions. In the crystal, chains running parallel to (001) are formed by N—H⋯O hydrogen bonds; these chains are linked into sheets parallel to (101) by C—H⋯O interactions.

Keywords: crystal structure; hydrogen bonding; copper complex.

CCDC reference: 1533763

Structure description

Pyrazolylacetamide derivatives have been evaluated for their in vitro activity as antimycobacterial agents against Mycobacterium smegmatis and also as anti-tuberculosis agents with low cytotoxicity (Emmadi et al., 2015 ). They also have therapeutic properties for the treatment of Cryptosporidium parasites (Sun et al., 2014 ). Their metal complexes have proven antimicrobial activities (Dholakiya et al., 2004 ) and may also have applications in catalysis (Jia et al., 2004 ). Continuing our research in this field (Chkirate et al., 2001 ), we have synthesized a copper perchlorate complex having as a ligand trans-bis-N-{2-[2-(5-methyl-1H-pyrazol-3-yl)acetamido]phenyl}benzamide obtained by reacting benzoyl chloride with N-2-aminophenyl-5-methyl-pyrazol-3-yl acetamide, the latter being obtained by the action of hydrazine on 4-(oxopropylidene)-1,5-benzodiazepin-2-one (El Abbassi et al., 1989 ).

The title compound (Fig. 1) has crystallographically imposed inversion symmetry with the organic ligands chelating through the tertiary nitrogen of the imidazole moiety (N1) and the oxygen (O1) of the proximate carbonyl group. Weak coordination of the perchlorate anions completes an axially elongated octahedral environment about the copper. The axial Cu1—O4 distance of 2.505 (3) Å is considerably longer than the equatorial Cu1—O1 distance of 1.9653 (17) Å, which is consistent with the action of the Jahn–Teller effect and is within the range 2.483 (13)–2.621 (6) Å previously cited for copper-bound perchlorate ions (Hueso-Ureña et al., 1999 ; Hong et al., 1987 ; Lu et al., 1987 ; Holló et al., 2013 ).

Figure 1
The title molecule with labeling scheme and 50% probability ellipsoids [symmetry code (i): −x + 1, −y + 1, −z + 1]. Intramolecular hydrogen bonds are shown as dashed lines.

In the crystal, pairwise N3—H3A⋯O2ⁱ hydrogen bonds form chains of complexes running parallel to the c axis, which are then associated via weak, pairwise C5—H5A⋯O2ⁱⁱ hydrogen bonds, forming layers parallel to (101) (Table 1 and Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O2ⁱ	0.91	1.97	2.870 (3)	171
N4—H4A⋯O3	0.91	2.08	2.971 (3)	166
C5—H5A⋯O5ⁱⁱ	0.99	2.48	3.358 (4)	148
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x+1, y, z.

Figure 2
Packing diagram showing the pairwise N—H⋯O and C—H⋯O hydrogen bonds as, respectively, blue and black dashed lines.

Synthesis and crystallization

0.125 mmol of Cu(ClO₄)₂·6H₂O dissolved in 2.5 ml of ethanol were added to a solution of 5 ml of methanol containing 0.25 mmol of trans-bis-N-{2-[2-(5-methyl-1H-pyrazol-3-yl)acetamido]phenyl}benzamide. The mixture was heated slightly and then left at room temperature. After filtration, blue–green single crystals were obtained.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[Cu(C₁₉H₁₈N₄O₂)₂(ClO₄)₂]
M_r	931.19
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	298
a, b, c (Å)	8.6572 (2), 8.8108 (2), 14.2054 (3)
α, β, γ (°)	79.406 (1), 86.240 (1), 67.895 (1)
V (Å³)	986.78 (4)
Z	1
Radiation type	Cu Kα
μ (mm⁻¹)	2.68
Crystal size (mm)	0.24 × 0.06 × 0.02

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.77, 0.95
No. of measured, independent and observed [I > 2σ(I)] reflections	7804, 3702, 2999
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.118, 1.04
No. of reflections	3702
No. of parameters	278
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.51
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL 2014/7 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1533763

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617002851/zq4016sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617002851/zq4016Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617002851/zq4016Isup3.cdx

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL 2014/7 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

trans-Bis(N-{2-[2-(3-methyl-1H-pyrazol-5-yl-κN²)acetamido-κO]phenyl}benzamide)bis(perchlorato-κO)copper(II) top

Crystal data top

[Cu(C₁₉H₁₈N₄O₂)₂(ClO₄)₂]	Z = 1
M_r = 931.19	F(000) = 479
Triclinic, P1	D_x = 1.567 Mg m⁻³
a = 8.6572 (2) Å	Cu Kα radiation, λ = 1.54178 Å
b = 8.8108 (2) Å	Cell parameters from 5387 reflections
c = 14.2054 (3) Å	θ = 5.5–71.9°
α = 79.406 (1)°	µ = 2.68 mm⁻¹
β = 86.240 (1)°	T = 298 K
γ = 67.895 (1)°	Plate, pale green-blue
V = 986.78 (4) Å³	0.24 × 0.06 × 0.02 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3702 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2999 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.033
Detector resolution: 10.4167 pixels mm^-1	θ_max = 71.9°, θ_min = 3.2°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −10→10
T_min = 0.77, T_max = 0.95	l = −17→17
7804 measured reflections

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)] = 0.044	Hydrogen site location: mixed
wR(F²) = 0.118	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0604P)² + 0.5402P] where P = (F_o² + 2F_c²)/3
3702 reflections	(Δ/σ)_max < 0.001
278 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Special details top

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. 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 > 2sigma(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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.98 Å) while those attached to nitrogen were placed in locations derived from a difference map and their parameters adjusted to give N—H = 0.91 Å. All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.5000	0.5000	0.0000	0.03299 (17)
O1	0.5561 (2)	0.5620 (2)	0.11555 (12)	0.0359 (4)
O2	0.2816 (3)	0.6621 (3)	0.54249 (14)	0.0454 (5)
N1	0.6439 (3)	0.2722 (3)	0.04252 (15)	0.0348 (5)
N2	0.6726 (3)	0.1487 (3)	−0.00892 (16)	0.0393 (5)
H2	0.6280	0.1756	−0.0688	0.047*
N3	0.5944 (3)	0.5296 (3)	0.27323 (14)	0.0312 (5)
H3A	0.6406	0.4602	0.3283	0.037*
N4	0.3221 (3)	0.5880 (3)	0.39480 (15)	0.0331 (5)
H4A	0.3106	0.5185	0.3580	0.040*
C1	0.8316 (5)	−0.1514 (4)	−0.0073 (3)	0.0580 (9)
H1A	0.8567	−0.1261	−0.0753	0.087*
H1B	0.7407	−0.1934	−0.0007	0.087*
H1C	0.9310	−0.2360	0.0259	0.087*
C2	0.7805 (4)	0.0020 (3)	0.0353 (2)	0.0388 (6)
C3	0.8220 (4)	0.0325 (3)	0.1198 (2)	0.0386 (6)
H3	0.8957	−0.0464	0.1676	0.046*
C4	0.7359 (3)	0.2003 (3)	0.12200 (18)	0.0308 (5)
C5	0.7426 (4)	0.2942 (4)	0.1983 (2)	0.0439 (7)
H5A	0.8567	0.2945	0.1991	0.053*
H5B	0.7253	0.2313	0.2607	0.053*
C6	0.6223 (3)	0.4703 (3)	0.19184 (17)	0.0295 (5)
C7	0.4904 (3)	0.6970 (3)	0.28058 (17)	0.0306 (5)
C8	0.5246 (4)	0.8292 (4)	0.2270 (2)	0.0403 (6)
H8	0.6167	0.8088	0.1844	0.048*
C9	0.4245 (4)	0.9903 (4)	0.2358 (2)	0.0466 (7)
H9	0.4472	1.0810	0.1990	0.056*
C10	0.2916 (4)	1.0194 (4)	0.2981 (2)	0.0473 (7)
H10	0.2222	1.1304	0.3035	0.057*
C11	0.2587 (4)	0.8881 (4)	0.3527 (2)	0.0414 (6)
H11	0.1683	0.9093	0.3964	0.050*
C12	0.3569 (3)	0.7258 (3)	0.34409 (18)	0.0317 (5)
C13	0.2845 (3)	0.5649 (3)	0.48871 (18)	0.0326 (6)
C14	0.2482 (3)	0.4123 (3)	0.52507 (18)	0.0332 (6)
C15	0.1334 (4)	0.4169 (4)	0.5994 (2)	0.0414 (7)
H15	0.0806	0.5160	0.6252	0.050*
C16	0.0962 (4)	0.2784 (4)	0.6353 (2)	0.0508 (8)
H16	0.0173	0.2825	0.6854	0.061*
C17	0.1736 (4)	0.1337 (4)	0.5985 (3)	0.0534 (8)
H17	0.1473	0.0385	0.6229	0.064*
C18	0.2895 (4)	0.1271 (4)	0.5261 (2)	0.0501 (8)
H18	0.3442	0.0266	0.5019	0.060*
C19	0.3261 (4)	0.2659 (4)	0.4889 (2)	0.0427 (7)
H19	0.4048	0.2611	0.4386	0.051*
Cl1	0.18597 (9)	0.49021 (9)	0.17026 (5)	0.04040 (19)
O3	0.3013 (4)	0.3972 (3)	0.24714 (19)	0.0717 (8)
O4	0.2600 (3)	0.4391 (3)	0.08272 (17)	0.0620 (7)
O5	0.0374 (4)	0.4586 (4)	0.1863 (2)	0.0851 (10)
O6	0.1550 (3)	0.6626 (3)	0.16559 (18)	0.0596 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0478 (3)	0.0250 (3)	0.0209 (3)	−0.0060 (2)	−0.0055 (2)	−0.0057 (2)
O1	0.0507 (11)	0.0292 (10)	0.0232 (9)	−0.0084 (9)	−0.0034 (8)	−0.0060 (7)
O2	0.0662 (14)	0.0425 (12)	0.0283 (10)	−0.0184 (10)	−0.0031 (9)	−0.0111 (8)
N1	0.0480 (13)	0.0280 (11)	0.0256 (11)	−0.0087 (10)	−0.0030 (9)	−0.0087 (9)
N2	0.0564 (15)	0.0291 (12)	0.0289 (12)	−0.0089 (11)	−0.0070 (10)	−0.0092 (9)
N3	0.0427 (12)	0.0303 (11)	0.0198 (10)	−0.0117 (10)	−0.0036 (8)	−0.0051 (8)
N4	0.0434 (13)	0.0344 (12)	0.0246 (11)	−0.0173 (10)	0.0019 (9)	−0.0074 (9)
C1	0.081 (3)	0.0332 (17)	0.054 (2)	−0.0087 (16)	−0.0120 (17)	−0.0168 (14)
C2	0.0506 (17)	0.0272 (14)	0.0359 (15)	−0.0106 (13)	0.0000 (12)	−0.0071 (11)
C3	0.0479 (17)	0.0264 (14)	0.0352 (14)	−0.0066 (12)	−0.0067 (12)	−0.0032 (11)
C4	0.0361 (14)	0.0270 (13)	0.0256 (12)	−0.0083 (11)	0.0002 (10)	−0.0032 (10)
C5	0.0532 (18)	0.0367 (16)	0.0332 (15)	−0.0029 (14)	−0.0118 (12)	−0.0110 (12)
C6	0.0359 (14)	0.0306 (13)	0.0233 (12)	−0.0132 (11)	−0.0021 (10)	−0.0049 (10)
C7	0.0417 (14)	0.0328 (13)	0.0209 (12)	−0.0160 (12)	−0.0037 (10)	−0.0073 (10)
C8	0.0558 (18)	0.0401 (16)	0.0303 (14)	−0.0235 (14)	0.0018 (12)	−0.0071 (11)
C9	0.070 (2)	0.0330 (15)	0.0412 (16)	−0.0250 (15)	−0.0026 (14)	−0.0038 (12)
C10	0.063 (2)	0.0284 (15)	0.0489 (18)	−0.0125 (14)	−0.0039 (14)	−0.0105 (12)
C11	0.0467 (17)	0.0371 (16)	0.0394 (16)	−0.0128 (13)	0.0009 (12)	−0.0103 (12)
C12	0.0410 (14)	0.0321 (13)	0.0250 (12)	−0.0157 (12)	−0.0045 (10)	−0.0059 (10)
C13	0.0336 (14)	0.0356 (14)	0.0251 (13)	−0.0086 (11)	−0.0033 (10)	−0.0048 (10)
C14	0.0349 (14)	0.0389 (15)	0.0246 (13)	−0.0126 (12)	−0.0043 (10)	−0.0029 (10)
C15	0.0366 (15)	0.0518 (18)	0.0303 (14)	−0.0113 (14)	−0.0006 (11)	−0.0046 (12)
C16	0.0439 (17)	0.063 (2)	0.0400 (17)	−0.0213 (16)	0.0019 (13)	0.0063 (15)
C17	0.0522 (19)	0.052 (2)	0.055 (2)	−0.0258 (17)	−0.0059 (15)	0.0094 (15)
C18	0.059 (2)	0.0389 (17)	0.0511 (19)	−0.0185 (15)	−0.0025 (15)	−0.0044 (14)
C19	0.0499 (17)	0.0412 (16)	0.0358 (15)	−0.0161 (14)	0.0061 (12)	−0.0071 (12)
Cl1	0.0501 (4)	0.0418 (4)	0.0345 (4)	−0.0215 (3)	0.0020 (3)	−0.0100 (3)
O3	0.112 (2)	0.0494 (15)	0.0563 (15)	−0.0322 (15)	−0.0350 (15)	0.0010 (11)
O4	0.0802 (17)	0.0741 (17)	0.0506 (14)	−0.0426 (14)	0.0204 (12)	−0.0341 (12)
O5	0.0719 (18)	0.116 (3)	0.098 (2)	−0.0652 (19)	0.0271 (16)	−0.0364 (19)
O6	0.0726 (16)	0.0368 (12)	0.0646 (15)	−0.0147 (12)	0.0087 (12)	−0.0122 (11)

Geometric parameters (Å, º) top

Cu1—N1ⁱ	1.928 (2)	C5—H5B	0.9900
Cu1—N1	1.928 (2)	C7—C8	1.388 (4)
Cu1—O1	1.9652 (17)	C7—C12	1.393 (4)
Cu1—O1ⁱ	1.9653 (17)	C8—C9	1.381 (4)
Cu1—O4	2.505 (3)	C8—H8	0.9500
O1—C6	1.252 (3)	C9—C10	1.378 (5)
O2—C13	1.241 (3)	C9—H9	0.9500
N1—C4	1.336 (3)	C10—C11	1.382 (4)
N1—N2	1.358 (3)	C10—H10	0.9500
N2—C2	1.345 (4)	C11—C12	1.385 (4)
N2—H2	0.9099	C11—H11	0.9500
N3—C6	1.326 (3)	C13—C14	1.488 (4)
N3—C7	1.429 (3)	C14—C19	1.388 (4)
N3—H3A	0.9099	C14—C15	1.397 (4)
N4—C13	1.349 (3)	C15—C16	1.378 (4)
N4—C12	1.418 (3)	C15—H15	0.9500
N4—H4A	0.9099	C16—C17	1.379 (5)
C1—C2	1.486 (4)	C16—H16	0.9500
C1—H1A	0.9800	C17—C18	1.382 (5)
C1—H1B	0.9800	C17—H17	0.9500
C1—H1C	0.9800	C18—C19	1.381 (4)
C2—C3	1.374 (4)	C18—H18	0.9500
C3—C4	1.389 (4)	C19—H19	0.9500
C3—H3	0.9500	Cl1—O5	1.411 (3)
C4—C5	1.495 (4)	Cl1—O6	1.429 (2)
C5—C6	1.498 (4)	Cl1—O4	1.430 (2)
C5—H5A	0.9900	Cl1—O3	1.435 (3)

N1ⁱ—Cu1—N1	180.0	C8—C7—N3	120.4 (2)
N1ⁱ—Cu1—O1	89.97 (8)	C12—C7—N3	119.1 (2)
N1—Cu1—O1	90.03 (8)	C9—C8—C7	119.8 (3)
N1ⁱ—Cu1—O1ⁱ	90.03 (8)	C9—C8—H8	120.1
N1—Cu1—O1ⁱ	89.97 (8)	C7—C8—H8	120.1
O1—Cu1—O1ⁱ	180.0	C10—C9—C8	120.0 (3)
C6—O1—Cu1	129.02 (17)	C10—C9—H9	120.0
C4—N1—N2	105.5 (2)	C8—C9—H9	120.0
C4—N1—Cu1	130.81 (17)	C9—C10—C11	120.4 (3)
N2—N1—Cu1	123.71 (17)	C9—C10—H10	119.8
C2—N2—N1	112.2 (2)	C11—C10—H10	119.8
C2—N2—H2	128.9	C10—C11—C12	120.4 (3)
N1—N2—H2	118.5	C10—C11—H11	119.8
C6—N3—C7	123.7 (2)	C12—C11—H11	119.8
C6—N3—H3A	119.1	C11—C12—C7	119.0 (3)
C7—N3—H3A	117.2	C11—C12—N4	122.2 (3)
C13—N4—C12	125.5 (2)	C7—C12—N4	118.8 (2)
C13—N4—H4A	118.6	O2—C13—N4	123.1 (3)
C12—N4—H4A	115.3	O2—C13—C14	121.4 (2)
C2—C1—H1A	109.5	N4—C13—C14	115.5 (2)
C2—C1—H1B	109.5	C19—C14—C15	119.2 (3)
H1A—C1—H1B	109.5	C19—C14—C13	122.4 (3)
C2—C1—H1C	109.5	C15—C14—C13	118.4 (3)
H1A—C1—H1C	109.5	C16—C15—C14	120.3 (3)
H1B—C1—H1C	109.5	C16—C15—H15	119.8
N2—C2—C3	105.6 (2)	C14—C15—H15	119.8
N2—C2—C1	122.0 (3)	C15—C16—C17	120.0 (3)
C3—C2—C1	132.4 (3)	C15—C16—H16	120.0
C2—C3—C4	107.1 (2)	C17—C16—H16	120.0
C2—C3—H3	126.4	C16—C17—C18	120.1 (3)
C4—C3—H3	126.4	C16—C17—H17	120.0
N1—C4—C3	109.6 (2)	C18—C17—H17	120.0
N1—C4—C5	122.9 (2)	C19—C18—C17	120.3 (3)
C3—C4—C5	127.4 (2)	C19—C18—H18	119.8
C4—C5—C6	118.1 (2)	C17—C18—H18	119.8
C4—C5—H5A	107.8	C18—C19—C14	120.0 (3)
C6—C5—H5A	107.8	C18—C19—H19	120.0
C4—C5—H5B	107.8	C14—C19—H19	120.0
C6—C5—H5B	107.8	O5—Cl1—O6	111.27 (18)
H5A—C5—H5B	107.1	O5—Cl1—O4	109.48 (17)
O1—C6—N3	120.3 (2)	O6—Cl1—O4	109.57 (15)
O1—C6—C5	124.1 (2)	O5—Cl1—O3	109.7 (2)
N3—C6—C5	115.5 (2)	O6—Cl1—O3	108.17 (15)
C8—C7—C12	120.4 (2)	O4—Cl1—O3	108.60 (18)

C4—N1—N2—C2	−0.5 (3)	C8—C9—C10—C11	0.7 (5)
Cu1—N1—N2—C2	178.5 (2)	C9—C10—C11—C12	−1.3 (5)
N1—N2—C2—C3	0.6 (3)	C10—C11—C12—C7	0.9 (4)
N1—N2—C2—C1	−179.8 (3)	C10—C11—C12—N4	−176.5 (3)
N2—C2—C3—C4	−0.5 (3)	C8—C7—C12—C11	0.2 (4)
C1—C2—C3—C4	−180.0 (3)	N3—C7—C12—C11	178.5 (2)
N2—N1—C4—C3	0.2 (3)	C8—C7—C12—N4	177.6 (2)
Cu1—N1—C4—C3	−178.8 (2)	N3—C7—C12—N4	−4.1 (3)
N2—N1—C4—C5	179.0 (3)	C13—N4—C12—C11	−46.5 (4)
Cu1—N1—C4—C5	0.1 (4)	C13—N4—C12—C7	136.2 (3)
C2—C3—C4—N1	0.2 (3)	C12—N4—C13—O2	−2.4 (4)
C2—C3—C4—C5	−178.6 (3)	C12—N4—C13—C14	178.4 (2)
N1—C4—C5—C6	9.1 (4)	O2—C13—C14—C19	−146.2 (3)
C3—C4—C5—C6	−172.3 (3)	N4—C13—C14—C19	33.1 (4)
Cu1—O1—C6—N3	−153.74 (19)	O2—C13—C14—C15	32.7 (4)
Cu1—O1—C6—C5	29.7 (4)	N4—C13—C14—C15	−148.0 (3)
C7—N3—C6—O1	−0.1 (4)	C19—C14—C15—C16	−1.0 (4)
C7—N3—C6—C5	176.8 (2)	C13—C14—C15—C16	−179.9 (2)
C4—C5—C6—O1	−24.4 (4)	C14—C15—C16—C17	0.6 (4)
C4—C5—C6—N3	158.8 (3)	C15—C16—C17—C18	0.5 (5)
C6—N3—C7—C8	−58.0 (3)	C16—C17—C18—C19	−1.3 (5)
C6—N3—C7—C12	123.7 (3)	C17—C18—C19—C14	0.9 (5)
C12—C7—C8—C9	−0.8 (4)	C15—C14—C19—C18	0.2 (4)
N3—C7—C8—C9	−179.1 (2)	C13—C14—C19—C18	179.1 (3)
C7—C8—C9—C10	0.4 (4)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2ⁱⁱ	0.91	1.97	2.870 (3)	171
N4—H4A···O3	0.91	2.08	2.971 (3)	166
C5—H5A···O5ⁱⁱⁱ	0.99	2.48	3.358 (4)	148

Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) x+1, y, z.

Acknowledgements

The support of NSF-MRI Grant #1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

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