Bis{μ(3)-cis-N-(2-carboxyl-ato-5-chloro-phen-yl)-N'-[3-(dimethyl-amino)-prop-yl]oxamidato(3-)}bis-(perchlorato-κO)bis-(N,N,N',N'-tetra-methyl-ethylene-diamine)-tetra-copper(II).

The title complex, [Cu(4)(C(14)H(15)ClN(3)O(4))(2)(ClO(4))(2)(C(6)H(16)N(2))(2)], is a tetra-nuclear copper(II) complex lying about an inversion center wherein a cis-oxamide group is coordinated to both Cu atoms with bite angles of 84.45 (6) and 84.08 (10)°. Both Cu atoms adopt distorted square-pyramidal coordination geometries. The apical position of one Cu atom is occupied by an O atom from a perchlorate group, with a Cu-O bond length of 2.519 (7) Å, while the apical site of the other Cu atom is occupied by a carboxyl-ate O atom with a Cu-O distance of 2.281 (3) Å. The Cu atoms bridged by oxamide and carboxyl-ate-group bridges are separated by 5.204 (6) and 5.603 (2) Å, respectively. The crystal structure is consolidated by weak inter-molecular C-H⋯O inter-actions. Two perchlorate O atoms are disordered with unequal site-occupancy factors.

Related literature

For the preparation of the Na[Cu(oxbm)] ligand, see: Tao et al. (2003 ▶). For a related crystal structure, see: Zang et al. (2003 ▶).

Experimental

Crystal data

[Cu4(C14H15ClN3O4)2(ClO4)2(C6H16N2)2]

M = 1334.96

Monoclinic,

a = 12.5750 (13) Å

b = 16.4137 (19) Å

c = 14.1080 (15) Å

β = 113.988 (2)°

V = 2660.4 (5) Å3

Z = 2

Mo Kα radiation

μ = 1.85 mm−1

T = 298 K

0.49 × 0.48 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.464, T max = 0.708

12993 measured reflections

4682 independent reflections

3287 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.133

S = 1.00

4682 reflections

359 parameters

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −0.76 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; 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: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811014978/pv2408sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014978/pv2408Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu4(C14H15ClN3O4)2(ClO4)2(C6H16N2)2]	F(000) = 1368
Mr = 1334.96	Dx = 1.666 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4604 reflections
a = 12.5750 (13) Å	θ = 2.2–27.7°
b = 16.4137 (19) Å	µ = 1.85 mm−1
c = 14.1080 (15) Å	T = 298 K
β = 113.988 (2)°	Block, green
V = 2660.4 (5) Å3	0.49 × 0.48 × 0.20 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	4682 independent reflections
Radiation source: fine-focus sealed tube	3287 reflections with I > 2σ(I)
graphite	Rint = 0.052
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→14
Tmin = 0.464, Tmax = 0.708	k = −19→19
12993 measured reflections	l = −16→14

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: inferred from neighbouring sites
wR(F2) = 0.133	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.072P)2 + 1.0008P] where P = (Fo2 + 2Fc2)/3
4682 reflections	(Δ/σ)max = 0.001
359 parameters	Δρmax = 0.65 e Å−3
0 restraints	Δρmin = −0.76 e Å−3

Experimental. Yield, 58%; analysis, calculated for C40H62Cl4N10O16Cu4: C 35.99, H, 4.68; N 10.49%; found: C 35.96, H 4.69, N, 10.51%.

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.28269 (4)	0.45069 (3)	0.33563 (4)	0.03039 (18)
Cu2	0.62990 (4)	0.24708 (3)	0.46234 (4)	0.03051 (18)
Cl1	0.79310 (12)	0.57100 (8)	0.29681 (13)	0.0599 (4)
Cl2	0.21665 (12)	0.38831 (7)	0.07826 (11)	0.0475 (3)
N1	0.4498 (3)	0.45347 (19)	0.3604 (3)	0.0243 (8)
N2	0.3096 (3)	0.3342 (2)	0.3638 (3)	0.0317 (9)
N3	0.1119 (3)	0.4486 (2)	0.3195 (3)	0.0315 (9)
N4	0.7940 (3)	0.2373 (2)	0.4680 (3)	0.0369 (10)
N5	0.6464 (3)	0.1307 (2)	0.5127 (3)	0.0324 (9)
O1	0.2790 (3)	0.56694 (18)	0.3491 (3)	0.0464 (9)
O2	0.3375 (3)	0.69384 (17)	0.3819 (3)	0.0403 (8)
O3	0.6008 (2)	0.35845 (17)	0.4019 (3)	0.0357 (8)
O4	0.4616 (3)	0.24340 (16)	0.4152 (3)	0.0345 (8)
O5	0.2228 (3)	0.4578 (2)	0.1424 (3)	0.0554 (10)
O6	0.1517 (4)	0.3248 (2)	0.0975 (4)	0.0762 (13)
O7	0.338 (3)	0.357 (2)	0.123 (4)	0.068 (5)	0.57
O8	0.190 (7)	0.4086 (18)	−0.022 (3)	0.082 (12)	0.57
O7'	0.322 (5)	0.363 (3)	0.081 (9)	0.076 (13)	0.43
O8'	0.143 (7)	0.415 (3)	−0.028 (4)	0.101 (13)	0.43
C1	0.3547 (4)	0.6219 (3)	0.3635 (3)	0.0316 (10)
C2	0.4679 (4)	0.6027 (2)	0.3540 (3)	0.0281 (10)
C3	0.5099 (3)	0.5233 (2)	0.3491 (3)	0.0253 (9)
C4	0.6111 (4)	0.5162 (3)	0.3307 (4)	0.0329 (11)
H4	0.6391	0.4649	0.3245	0.039*
C5	0.6689 (4)	0.5847 (3)	0.3218 (4)	0.0373 (11)
C6	0.6330 (4)	0.6620 (3)	0.3304 (4)	0.0405 (12)
H6	0.6746	0.7074	0.3256	0.049*
C7	0.5320 (4)	0.6699 (3)	0.3468 (4)	0.0348 (11)
H7	0.5061	0.7218	0.3531	0.042*
C8	0.4971 (4)	0.3808 (2)	0.3830 (3)	0.0274 (10)
C9	0.4166 (4)	0.3140 (2)	0.3888 (3)	0.0283 (10)
C10	0.2293 (4)	0.2683 (3)	0.3600 (5)	0.0467 (14)
H10A	0.2696	0.2291	0.4144	0.056*
H10B	0.2047	0.2404	0.2939	0.056*
C11	0.1226 (4)	0.2997 (3)	0.3737 (5)	0.0480 (13)
H11A	0.0699	0.2546	0.3659	0.058*
H11B	0.1466	0.3208	0.4435	0.058*
C12	0.0582 (4)	0.3660 (3)	0.2967 (4)	0.0430 (12)
H12A	0.0517	0.3496	0.2286	0.052*
H12B	−0.0201	0.3698	0.2937	0.052*
C13	0.0402 (4)	0.5036 (3)	0.2348 (4)	0.0489 (14)
H13A	0.0374	0.4834	0.1700	0.073*
H13B	0.0738	0.5572	0.2472	0.073*
H13C	−0.0373	0.5061	0.2322	0.073*
C14	0.1120 (5)	0.4791 (4)	0.4192 (5)	0.0569 (15)
H14A	0.1497	0.5313	0.4353	0.085*
H14B	0.1530	0.4413	0.4738	0.085*
H14C	0.0332	0.4844	0.4126	0.085*
C15	0.8213 (5)	0.1484 (3)	0.4798 (5)	0.0523 (14)
H15A	0.9049	0.1404	0.5088	0.063*
H15B	0.7881	0.1220	0.4125	0.063*
C16	0.7717 (4)	0.1115 (3)	0.5501 (5)	0.0500 (14)
H16A	0.7823	0.0528	0.5524	0.060*
H16B	0.8127	0.1326	0.6199	0.060*
C17	0.7999 (6)	0.2666 (4)	0.3708 (6)	0.077 (2)
H17A	0.7737	0.3221	0.3585	0.115*
H17B	0.7510	0.2332	0.3139	0.115*
H17C	0.8787	0.2634	0.3772	0.115*
C18	0.8777 (4)	0.2825 (4)	0.5567 (5)	0.0631 (17)
H18A	0.9546	0.2755	0.5593	0.095*
H18B	0.8753	0.2622	0.6197	0.095*
H18C	0.8577	0.3393	0.5493	0.095*
C19	0.5771 (4)	0.0761 (3)	0.4248 (4)	0.0449 (13)
H19A	0.6019	0.0830	0.3694	0.067*
H19B	0.4961	0.0897	0.4007	0.067*
H19C	0.5887	0.0205	0.4478	0.067*
C20	0.6059 (5)	0.1191 (3)	0.5964 (4)	0.0523 (14)
H20A	0.6208	0.0640	0.6212	0.078*
H20B	0.5239	0.1298	0.5700	0.078*
H20C	0.6467	0.1559	0.6523	0.078*

	U11	U22	U33	U12	U13	U23
Cu1	0.0262 (3)	0.0263 (3)	0.0462 (4)	0.0015 (2)	0.0225 (3)	−0.0014 (2)
Cu2	0.0285 (3)	0.0249 (3)	0.0457 (4)	0.0043 (2)	0.0227 (3)	0.0056 (2)
Cl1	0.0542 (9)	0.0542 (8)	0.1007 (12)	0.0039 (7)	0.0617 (8)	0.0139 (8)
Cl2	0.0699 (9)	0.0377 (7)	0.0526 (8)	−0.0002 (6)	0.0430 (7)	0.0007 (6)
N1	0.0249 (19)	0.0217 (18)	0.031 (2)	0.0019 (15)	0.0163 (16)	0.0022 (15)
N2	0.027 (2)	0.0250 (18)	0.050 (2)	−0.0018 (16)	0.0230 (18)	0.0045 (17)
N3	0.0229 (19)	0.038 (2)	0.041 (2)	0.0017 (16)	0.0203 (17)	−0.0030 (17)
N4	0.032 (2)	0.034 (2)	0.054 (3)	0.0090 (17)	0.026 (2)	0.0059 (19)
N5	0.039 (2)	0.0243 (18)	0.036 (2)	0.0013 (17)	0.0172 (18)	0.0004 (16)
O1	0.0350 (19)	0.0281 (17)	0.087 (3)	0.0014 (15)	0.0353 (18)	−0.0093 (17)
O2	0.056 (2)	0.0250 (16)	0.057 (2)	0.0041 (15)	0.0403 (18)	−0.0023 (15)
O3	0.0270 (17)	0.0291 (16)	0.059 (2)	0.0048 (13)	0.0256 (15)	0.0134 (15)
O4	0.0277 (17)	0.0231 (16)	0.055 (2)	0.0021 (13)	0.0191 (15)	0.0086 (14)
O5	0.081 (3)	0.046 (2)	0.051 (2)	0.0051 (19)	0.039 (2)	−0.0035 (17)
O6	0.088 (3)	0.060 (3)	0.100 (4)	−0.019 (2)	0.058 (3)	−0.002 (2)
O7	0.081 (9)	0.068 (7)	0.082 (15)	0.019 (7)	0.061 (11)	0.005 (10)
O8	0.16 (3)	0.049 (8)	0.048 (14)	−0.002 (12)	0.056 (16)	0.000 (7)
O7'	0.074 (16)	0.071 (12)	0.11 (4)	−0.003 (10)	0.07 (2)	−0.012 (19)
O8'	0.13 (3)	0.082 (14)	0.055 (13)	0.019 (15)	−0.002 (14)	0.016 (9)
C1	0.042 (3)	0.030 (2)	0.032 (3)	0.001 (2)	0.025 (2)	0.000 (2)
C2	0.036 (3)	0.030 (2)	0.026 (2)	0.000 (2)	0.020 (2)	−0.0025 (18)
C3	0.029 (2)	0.026 (2)	0.027 (2)	−0.0018 (18)	0.0173 (19)	0.0029 (18)
C4	0.036 (3)	0.030 (2)	0.042 (3)	0.005 (2)	0.025 (2)	0.009 (2)
C5	0.036 (3)	0.043 (3)	0.046 (3)	0.002 (2)	0.030 (2)	0.009 (2)
C6	0.048 (3)	0.035 (3)	0.050 (3)	−0.005 (2)	0.033 (3)	0.006 (2)
C7	0.044 (3)	0.025 (2)	0.046 (3)	−0.001 (2)	0.028 (2)	0.000 (2)
C8	0.029 (2)	0.028 (2)	0.031 (2)	0.0000 (19)	0.019 (2)	0.0015 (18)
C9	0.030 (2)	0.028 (2)	0.036 (3)	0.0021 (19)	0.022 (2)	0.0031 (19)
C10	0.035 (3)	0.037 (3)	0.077 (4)	−0.007 (2)	0.031 (3)	0.006 (3)
C11	0.036 (3)	0.047 (3)	0.072 (4)	−0.006 (2)	0.032 (3)	0.007 (3)
C12	0.024 (2)	0.050 (3)	0.057 (3)	−0.004 (2)	0.019 (2)	−0.003 (3)
C13	0.033 (3)	0.056 (3)	0.065 (4)	0.012 (2)	0.027 (3)	0.015 (3)
C14	0.056 (4)	0.070 (4)	0.058 (4)	0.004 (3)	0.038 (3)	−0.012 (3)
C15	0.043 (3)	0.042 (3)	0.081 (4)	0.009 (2)	0.035 (3)	−0.006 (3)
C16	0.039 (3)	0.035 (3)	0.069 (4)	0.009 (2)	0.015 (3)	0.010 (3)
C17	0.066 (4)	0.095 (5)	0.094 (5)	0.017 (4)	0.059 (4)	0.027 (4)
C18	0.036 (3)	0.055 (3)	0.102 (5)	−0.003 (3)	0.032 (3)	−0.015 (3)
C19	0.049 (3)	0.033 (3)	0.052 (3)	−0.008 (2)	0.020 (3)	−0.004 (2)
C20	0.080 (4)	0.034 (3)	0.058 (4)	0.001 (3)	0.043 (3)	0.007 (2)

Cu1—O1	1.920 (3)	C4—C5	1.373 (6)
Cu1—N2	1.953 (3)	C4—H4	0.9300
Cu1—N1	1.986 (3)	C5—C6	1.368 (6)
Cu1—N3	2.066 (3)	C6—C7	1.385 (7)
Cu1—O5	2.518 (4)	C6—H6	0.9300
Cu2—O4	1.944 (3)	C7—H7	0.9300
Cu2—O3	1.987 (3)	C8—C9	1.516 (6)
Cu2—N5	2.020 (3)	C10—C11	1.521 (7)
Cu2—N4	2.039 (4)	C10—H10A	0.9700
Cu2—O2i	2.281 (3)	C10—H10B	0.9700
Cl1—C5	1.750 (5)	C11—C12	1.519 (7)
Cl2—O8	1.36 (4)	C11—H11A	0.9700
Cl2—O7'	1.37 (4)	C11—H11B	0.9700
Cl2—O6	1.417 (4)	C12—H12A	0.9700
Cl2—O5	1.439 (4)	C12—H12B	0.9700
Cl2—O8'	1.47 (4)	C13—H13A	0.9600
Cl2—O7	1.48 (3)	C13—H13B	0.9600
N1—C8	1.313 (5)	C13—H13C	0.9600
N1—C3	1.416 (5)	C14—H14A	0.9600
N2—C9	1.288 (5)	C14—H14B	0.9600
N2—C10	1.467 (5)	C14—H14C	0.9600
N3—C13	1.476 (6)	C15—C16	1.497 (8)
N3—C12	1.490 (6)	C15—H15A	0.9700
N3—C14	1.492 (6)	C15—H15B	0.9700
N4—C18	1.468 (7)	C16—H16A	0.9700
N4—C17	1.482 (7)	C16—H16B	0.9700
N4—C15	1.493 (6)	C17—H17A	0.9600
N5—C20	1.475 (6)	C17—H17B	0.9600
N5—C16	1.478 (6)	C17—H17C	0.9600
N5—C19	1.490 (6)	C18—H18A	0.9600
O1—C1	1.266 (5)	C18—H18B	0.9600
O2—C1	1.247 (5)	C18—H18C	0.9600
O2—Cu2i	2.281 (3)	C19—H19A	0.9600
O3—C8	1.275 (5)	C19—H19B	0.9600
O4—C9	1.278 (5)	C19—H19C	0.9600
C1—C2	1.517 (6)	C20—H20A	0.9600
C2—C7	1.394 (6)	C20—H20B	0.9600
C2—C3	1.418 (6)	C20—H20C	0.9600
C3—C4	1.404 (6)
O1—Cu1—N2	164.01 (16)	C5—C6—H6	121.3
O1—Cu1—N1	91.51 (13)	C7—C6—H6	121.3
N2—Cu1—N1	84.45 (13)	C6—C7—C2	122.3 (4)
O1—Cu1—N3	87.77 (13)	C6—C7—H7	118.8
N2—Cu1—N3	95.33 (14)	C2—C7—H7	118.8
N1—Cu1—N3	176.48 (14)	O3—C8—N1	129.5 (4)
O1—Cu1—O5	93.01 (14)	O3—C8—C9	115.4 (4)
N2—Cu1—O5	102.50 (14)	N1—C8—C9	115.1 (4)
N1—Cu1—O5	91.09 (14)	O4—C9—N2	127.1 (4)
N3—Cu1—O5	92.39 (14)	O4—C9—C8	116.4 (4)
O4—Cu2—O3	84.08 (11)	N2—C9—C8	116.4 (4)
O4—Cu2—N5	91.89 (13)	N2—C10—C11	112.0 (4)
O3—Cu2—N5	174.85 (13)	N2—C10—H10A	109.2
O4—Cu2—N4	162.63 (15)	C11—C10—H10A	109.2
O3—Cu2—N4	95.52 (13)	N2—C10—H10B	109.2
N5—Cu2—N4	87.36 (15)	C11—C10—H10B	109.2
O4—Cu2—O2i	95.00 (13)	H10A—C10—H10B	107.9
O3—Cu2—O2i	87.23 (12)	C12—C11—C10	113.2 (4)
N5—Cu2—O2i	96.35 (13)	C12—C11—H11A	108.9
N4—Cu2—O2i	102.33 (14)	C10—C11—H11A	108.9
O8—Cl2—O7'	86 (2)	C12—C11—H11B	108.9
O8—Cl2—O6	118 (2)	C10—C11—H11B	108.9
O7'—Cl2—O6	113 (3)	H11A—C11—H11B	107.7
O8—Cl2—O5	112.9 (13)	N3—C12—C11	115.8 (4)
O7'—Cl2—O5	114 (3)	N3—C12—H12A	108.3
O6—Cl2—O5	110.6 (3)	C11—C12—H12A	108.3
O7'—Cl2—O8'	109.0 (19)	N3—C12—H12B	108.3
O6—Cl2—O8'	104 (3)	C11—C12—H12B	108.3
O5—Cl2—O8'	105 (3)	H12A—C12—H12B	107.4
O8—Cl2—O7	107.8 (17)	N3—C13—H13A	109.5
O6—Cl2—O7	103.5 (14)	N3—C13—H13B	109.5
O5—Cl2—O7	102.8 (17)	H13A—C13—H13B	109.5
O8'—Cl2—O7	131 (3)	N3—C13—H13C	109.5
C8—N1—C3	123.6 (4)	H13A—C13—H13C	109.5
C8—N1—Cu1	111.3 (3)	H13B—C13—H13C	109.5
C3—N1—Cu1	125.0 (3)	N3—C14—H14A	109.5
C9—N2—C10	116.6 (4)	N3—C14—H14B	109.5
C9—N2—Cu1	112.5 (3)	H14A—C14—H14B	109.5
C10—N2—Cu1	130.9 (3)	N3—C14—H14C	109.5
C13—N3—C12	107.9 (4)	H14A—C14—H14C	109.5
C13—N3—C14	108.9 (4)	H14B—C14—H14C	109.5
C12—N3—C14	109.6 (4)	N4—C15—C16	109.4 (4)
C13—N3—Cu1	110.2 (3)	N4—C15—H15A	109.8
C12—N3—Cu1	113.5 (3)	C16—C15—H15A	109.8
C14—N3—Cu1	106.8 (3)	N4—C15—H15B	109.8
C18—N4—C17	109.7 (5)	C16—C15—H15B	109.8
C18—N4—C15	110.3 (4)	H15A—C15—H15B	108.3
C17—N4—C15	109.0 (4)	N5—C16—C15	110.3 (4)
C18—N4—Cu2	110.8 (3)	N5—C16—H16A	109.6
C17—N4—Cu2	111.6 (3)	C15—C16—H16A	109.6
C15—N4—Cu2	105.3 (3)	N5—C16—H16B	109.6
C20—N5—C16	110.6 (4)	C15—C16—H16B	109.6
C20—N5—C19	108.2 (4)	H16A—C16—H16B	108.1
C16—N5—C19	110.3 (4)	N4—C17—H17A	109.5
C20—N5—Cu2	112.6 (3)	N4—C17—H17B	109.5
C16—N5—Cu2	105.6 (3)	H17A—C17—H17B	109.5
C19—N5—Cu2	109.5 (3)	N4—C17—H17C	109.5
C1—O1—Cu1	132.6 (3)	H17A—C17—H17C	109.5
C1—O2—Cu2i	128.7 (3)	H17B—C17—H17C	109.5
C8—O3—Cu2	110.4 (3)	N4—C18—H18A	109.5
C9—O4—Cu2	111.3 (3)	N4—C18—H18B	109.5
Cl2—O5—Cu1	124.0 (2)	H18A—C18—H18B	109.5
O2—C1—O1	121.7 (4)	N4—C18—H18C	109.5
O2—C1—C2	117.6 (4)	H18A—C18—H18C	109.5
O1—C1—C2	120.6 (4)	H18B—C18—H18C	109.5
C7—C2—C3	119.1 (4)	N5—C19—H19A	109.5
C7—C2—C1	115.7 (4)	N5—C19—H19B	109.5
C3—C2—C1	125.2 (4)	H19A—C19—H19B	109.5
C4—C3—N1	121.3 (4)	N5—C19—H19C	109.5
C4—C3—C2	117.9 (4)	H19A—C19—H19C	109.5
N1—C3—C2	120.8 (4)	H19B—C19—H19C	109.5
C5—C4—C3	120.2 (4)	N5—C20—H20A	109.5
C5—C4—H4	119.9	N5—C20—H20B	109.5
C3—C4—H4	119.9	H20A—C20—H20B	109.5
C6—C5—C4	123.0 (4)	N5—C20—H20C	109.5
C6—C5—Cl1	119.5 (4)	H20A—C20—H20C	109.5
C4—C5—Cl1	117.5 (4)	H20B—C20—H20C	109.5
C5—C6—C7	117.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O7ii	0.93	2.58	3.26 (3)	129
C16—H16A···O8iii	0.97	2.46	3.41 (3)	168
C20—H20C···O2i	0.96	2.54	3.139 (6)	121
C4—H4···O3	0.93	2.21	2.799 (5)	120
C7—H7···O2	0.93	2.36	2.714 (6)	102
C13—H13A···O5	0.96	2.55	3.158 (7)	121
C13—H13B···O1	0.96	2.39	2.960 (6)	118
C14—H14A···O1	0.96	2.46	3.026 (7)	117
C17—H17A···O3	0.96	2.56	3.103 (7)	116
C19—H19B···O4	0.96	2.58	3.084 (6)	113

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O7i	0.93	2.58	3.26 (3)	129
C16—H16A⋯O8ii	0.97	2.46	3.41 (3)	168
C20—H20C⋯O2iii	0.96	2.54	3.139 (6)	121

Symmetry codes: (i) ; (ii) ; (iii) .