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Binuclear and tetra­nuclear copper(II) complexes are of inter­est because of their structural, magnetic and photoluminescence properties. Of the several important configurations of tetra­nuclear copper(II) complexes, there are limited reports on the crystal structures and solid-state photoluminescence properties of `stepped' tetra­nuclear copper(II) complexes. A new CuII complex, namely bis­{μ3-3-[(4-meth­oxy-2-oxido­benzyl­idene)amino]­propano­lato}bis­{μ2-3-[(4-meth­oxy-2-oxido­benzyl­idene)amino]­propano­lato}tetra­copper(II), [Cu4(C11H13NO3)4], has been synthesized and characterized using elemental analysis, FT–IR, solid-state UV–Vis spectroscopy and single-crystal X-ray diffraction. The crystal structure determination shows that the complex is a stepped tetra­nuclear structure con­sisting of two dinuclear [Cu2(L)2] units {L is 3-[(4-meth­oxy-2-oxido­benzyl­idene)amino]­propano­late}. The two terminal CuII atoms are four-coordinated in square-planar environments, while the two central CuII atoms are five-coordinated in square-pyramidal environments. The solid-state photoluminescence properties of both the complex and 3-[(2-hy­droxy-4-meth­oxy­benzyl­idene)amino]­propanol (H2L) have been investigated at room temperature in the visible region. When the complex and H2L are excited under UV light at 349 nm, the complex displays a strong blue emission at 469 nm and H2L displays a green emission at 515 nm.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617004946/lf3047sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617004946/lf3047Isup2.hkl
Contains datablock I

CCDC reference: 1521958

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2006).

Bis{µ3-3-[(4-methoxy-2-oxidobenzylidene)amino]propanolato}bis{µ2-3-[(4-methoxy-2-oxidobenzylidene)amino]propanolato}tetracopper(II) top
Crystal data top
[Cu4(C11H13NO3)4]F(000) = 1112
Mr = 1083.05Dx = 1.684 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 16.2592 (3) ÅCell parameters from 846 reflections
b = 14.2078 (3) Åθ = 2.6–25.5°
c = 9.2560 (2) ŵ = 2.03 mm1
β = 92.527 (1)°T = 100 K
V = 2136.13 (8) Å3Plate, violet
Z = 20.17 × 0.16 × 0.06 mm
Data collection top
Bruker APEXII with a CCD area detector
diffractometer
5655 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
phi and ω scansθmax = 33.4°, θmin = 1.3°
Absorption correction: multi-scan
(TWINABS; Sheldrick, 2008b)
h = 024
Tmin = 0.767, Tmax = 0.885k = 210
8050 measured reflectionsl = 1414
8050 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.123 w = 1/[σ2(Fo2) + (0.0276P)2 + 3.965P]
where P = (Fo2 + 2Fc2)/3
S = 1.21(Δ/σ)max = 0.001
8050 reflectionsΔρmax = 0.74 e Å3
348 parametersΔρmin = 0.58 e Å3
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. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cu10.28607 (2)0.38313 (3)0.07394 (4)0.02378 (9)
Cu20.47193 (2)0.39545 (3)0.07983 (4)0.02041 (9)
O10.37587 (12)0.39379 (16)0.0522 (2)0.0234 (4)
O20.21254 (12)0.36940 (17)0.2266 (2)0.0259 (5)
O30.04308 (14)0.3618 (2)0.4600 (3)0.0395 (6)
O40.38181 (12)0.36959 (15)0.2028 (2)0.0212 (4)
O50.54848 (12)0.42022 (15)0.0683 (2)0.0209 (4)
O60.80182 (13)0.38723 (17)0.3068 (2)0.0281 (5)
C1A0.37454 (19)0.4003 (3)0.2044 (3)0.0276 (6)0.498 (10)
H1AA0.4168110.3577160.2419900.033*0.498 (10)
H1AB0.3883720.4653870.2326200.033*0.498 (10)
C2A0.2896 (4)0.3737 (6)0.2724 (6)0.0269 (16)0.498 (10)
H2AA0.2911950.3779030.3789580.032*0.498 (10)
H2AB0.2766810.3078560.2469510.032*0.498 (10)
C3A0.2224 (4)0.4381 (6)0.2204 (6)0.0272 (18)0.498 (10)
H3AA0.2415440.5041460.2238510.033*0.498 (10)
H3AB0.1730680.4322180.2863850.033*0.498 (10)
N1A0.1998 (5)0.4155 (6)0.0720 (9)0.0237 (15)0.498 (10)
C4A0.1229 (2)0.3951 (4)0.0512 (4)0.0562 (14)0.498 (10)
H4A0.0881190.3855970.1351810.067*0.498 (10)
C1B0.37454 (19)0.4003 (3)0.2044 (3)0.0276 (6)0.502 (10)
H1BA0.3872890.3378420.2453170.033*0.502 (10)
H1BB0.4176980.4448380.2330350.033*0.502 (10)
C2B0.2933 (4)0.4326 (7)0.2652 (7)0.032 (2)0.502 (10)
H2BA0.2964110.4395360.3712490.039*0.502 (10)
H2BB0.2812320.4953650.2248270.039*0.502 (10)
C3B0.2240 (4)0.3672 (8)0.2342 (7)0.039 (3)0.502 (10)
H3BA0.1755490.3829370.2981510.047*0.502 (10)
H3BB0.2405520.3017750.2555130.047*0.502 (10)
N1B0.2012 (5)0.3740 (7)0.0797 (9)0.0277 (17)0.502 (10)
C4B0.1229 (2)0.3951 (4)0.0512 (4)0.0562 (14)0.502 (10)
H4B0.0889580.4185640.1292980.067*0.502 (10)
C50.0860 (2)0.3856 (3)0.0843 (3)0.0350 (8)
C60.13247 (18)0.3733 (2)0.2178 (3)0.0262 (6)
C70.08859 (18)0.3640 (2)0.3459 (3)0.0266 (6)
H70.1179800.3548490.4357510.032*
C80.0033 (2)0.3682 (3)0.3419 (4)0.0314 (7)
C90.0422 (2)0.3796 (3)0.2103 (4)0.0387 (9)
H90.1006370.3811710.2082140.046*
C100.0011 (2)0.3882 (3)0.0860 (4)0.0419 (9)
H100.0319360.3963850.0027560.050*
C110.0017 (2)0.3665 (3)0.5997 (4)0.0381 (9)
H11A0.0346930.3119660.6130420.057*
H11B0.0424860.3664160.6746180.057*
H11C0.0309150.4244600.6070710.057*
C12A0.38366 (19)0.3635 (2)0.3554 (3)0.0243 (6)0.685 (9)
H12A0.3356670.3267340.3856290.029*0.685 (9)
H12B0.3796710.4275210.3968160.029*0.685 (9)
C13A0.4644 (3)0.3157 (3)0.4149 (4)0.0220 (11)0.685 (9)
H13A0.4615640.3077970.5207890.026*0.685 (9)
H13B0.4684420.2522370.3715640.026*0.685 (9)
C14A0.5412 (3)0.3707 (5)0.3836 (5)0.0247 (11)0.685 (9)
H14A0.5343210.4364250.4164700.030*0.685 (9)
H14B0.5884570.3432500.4399010.030*0.685 (9)
N2A0.5596 (5)0.3712 (5)0.2307 (9)0.0200 (12)0.685 (9)
C15A0.62992 (19)0.3384 (3)0.1943 (3)0.0295 (7)0.685 (9)
H15A0.6614710.3057340.2671870.035*0.685 (9)
C12B0.38366 (19)0.3635 (2)0.3554 (3)0.0243 (6)0.315 (9)
H12C0.3700980.2984460.3841720.029*0.315 (9)
H12D0.3413920.4060340.3930910.029*0.315 (9)
C13B0.4644 (6)0.3892 (7)0.4192 (9)0.024 (2)0.315 (9)
H13C0.4632520.3869900.5259970.028*0.315 (9)
H13D0.4786560.4540410.3903330.028*0.315 (9)
C14B0.5283 (7)0.3209 (11)0.3675 (10)0.028 (3)0.315 (9)
H14C0.5783660.3242930.4320460.033*0.315 (9)
H14D0.5064790.2559010.3711960.033*0.315 (9)
N2B0.5494 (11)0.3433 (11)0.2190 (19)0.017 (3)0.315 (9)
C15B0.62992 (19)0.3384 (3)0.1943 (3)0.0295 (7)0.315 (9)
H15B0.6666800.3289940.2756800.035*0.315 (9)
C160.66532 (17)0.3459 (2)0.0556 (3)0.0220 (5)
C170.62523 (17)0.3916 (2)0.0659 (3)0.0200 (5)
C180.67166 (17)0.4068 (2)0.1896 (3)0.0211 (5)
H180.6473350.4387720.2708450.025*
C190.75224 (17)0.3755 (2)0.1934 (3)0.0215 (5)
C200.79026 (19)0.3267 (2)0.0757 (3)0.0268 (6)
H200.8446860.3029900.0810510.032*
C210.74726 (18)0.3143 (2)0.0454 (3)0.0245 (6)
H210.7732150.2833500.1261470.029*
C220.7697 (2)0.4359 (3)0.4321 (3)0.0306 (7)
H22A0.7196920.4042200.4696950.046*
H22B0.8108520.4361090.5062820.046*
H22C0.7564970.5009180.4060970.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.01875 (17)0.0373 (2)0.01511 (15)0.00328 (15)0.00174 (12)0.00247 (14)
Cu20.01825 (16)0.02807 (19)0.01484 (14)0.00302 (14)0.00010 (11)0.00193 (13)
O10.0210 (9)0.0340 (12)0.0150 (8)0.0007 (9)0.0003 (7)0.0001 (8)
O20.0151 (9)0.0426 (13)0.0198 (9)0.0014 (9)0.0014 (7)0.0038 (9)
O30.0197 (11)0.0725 (19)0.0263 (11)0.0028 (11)0.0006 (9)0.0019 (12)
O40.0196 (9)0.0286 (11)0.0153 (8)0.0004 (8)0.0003 (7)0.0039 (8)
O50.0165 (9)0.0272 (11)0.0191 (9)0.0030 (7)0.0015 (7)0.0019 (8)
O60.0213 (10)0.0393 (13)0.0239 (10)0.0025 (9)0.0034 (8)0.0025 (9)
C1A0.0273 (15)0.0387 (18)0.0167 (12)0.0018 (13)0.0003 (10)0.0051 (12)
C2A0.037 (4)0.028 (4)0.016 (2)0.002 (3)0.005 (2)0.001 (2)
C3A0.031 (3)0.036 (5)0.014 (2)0.010 (3)0.004 (2)0.007 (2)
N1A0.026 (3)0.029 (4)0.016 (2)0.001 (3)0.000 (2)0.002 (3)
C4A0.0244 (16)0.123 (5)0.0200 (15)0.010 (2)0.0071 (13)0.008 (2)
C1B0.0273 (15)0.0387 (18)0.0167 (12)0.0018 (13)0.0003 (10)0.0051 (12)
C2B0.033 (4)0.049 (6)0.015 (3)0.007 (3)0.003 (2)0.006 (3)
C3B0.024 (3)0.075 (7)0.019 (3)0.022 (4)0.007 (2)0.007 (3)
N1B0.026 (3)0.041 (5)0.015 (2)0.005 (4)0.004 (2)0.000 (4)
C4B0.0244 (16)0.123 (5)0.0200 (15)0.010 (2)0.0071 (13)0.008 (2)
C50.0222 (14)0.061 (2)0.0211 (13)0.0102 (15)0.0040 (11)0.0069 (15)
C60.0180 (12)0.0384 (18)0.0218 (12)0.0037 (12)0.0029 (10)0.0003 (12)
C70.0190 (13)0.0402 (18)0.0205 (12)0.0015 (12)0.0017 (10)0.0017 (12)
C80.0213 (14)0.046 (2)0.0265 (14)0.0058 (13)0.0023 (11)0.0015 (14)
C90.0196 (14)0.067 (3)0.0295 (16)0.0015 (16)0.0045 (12)0.0004 (16)
C100.0246 (15)0.071 (3)0.0291 (16)0.0043 (17)0.0092 (13)0.0050 (17)
C110.0206 (14)0.069 (3)0.0252 (14)0.0034 (15)0.0018 (12)0.0017 (16)
C12A0.0237 (14)0.0331 (16)0.0161 (11)0.0001 (12)0.0010 (10)0.0045 (11)
C13A0.025 (2)0.027 (3)0.0135 (16)0.0014 (17)0.0015 (14)0.0048 (15)
C14A0.022 (2)0.037 (3)0.0148 (18)0.008 (2)0.0009 (15)0.0012 (19)
N2A0.018 (3)0.025 (4)0.017 (2)0.006 (2)0.0037 (17)0.002 (2)
C15A0.0240 (14)0.0435 (19)0.0205 (13)0.0037 (13)0.0043 (11)0.0085 (13)
C12B0.0237 (14)0.0331 (16)0.0161 (11)0.0001 (12)0.0010 (10)0.0045 (11)
C13B0.029 (5)0.026 (6)0.015 (4)0.006 (4)0.001 (3)0.002 (3)
C14B0.034 (6)0.041 (7)0.008 (3)0.001 (5)0.004 (3)0.004 (4)
N2B0.012 (5)0.025 (8)0.013 (4)0.007 (5)0.002 (3)0.006 (5)
C15B0.0240 (14)0.0435 (19)0.0205 (13)0.0037 (13)0.0043 (11)0.0085 (13)
C160.0200 (13)0.0252 (14)0.0205 (12)0.0022 (11)0.0002 (10)0.0027 (11)
C170.0206 (12)0.0205 (13)0.0186 (11)0.0004 (11)0.0015 (9)0.0024 (10)
C180.0201 (12)0.0241 (14)0.0189 (11)0.0024 (10)0.0008 (10)0.0006 (10)
C190.0183 (12)0.0247 (14)0.0220 (12)0.0009 (10)0.0052 (10)0.0008 (10)
C200.0187 (13)0.0317 (17)0.0299 (14)0.0046 (12)0.0012 (11)0.0002 (12)
C210.0177 (12)0.0297 (16)0.0257 (13)0.0039 (11)0.0028 (10)0.0035 (12)
C220.0261 (15)0.0434 (19)0.0226 (13)0.0030 (14)0.0056 (11)0.0028 (13)
Geometric parameters (Å, º) top
Cu1—O11.916 (2)C5—C101.418 (5)
Cu1—O21.900 (2)C6—C71.416 (4)
Cu1—O41.928 (2)C7—H70.9500
Cu1—N1A1.959 (8)C7—C81.387 (4)
Cu1—N1B1.942 (8)C8—C91.406 (5)
Cu2—O11.941 (2)C9—H90.9500
Cu2—O41.930 (2)C9—C101.361 (5)
Cu2—O51.9242 (19)C10—H100.9500
Cu2—O5i2.641 (2)C11—H11A0.9800
Cu2—N2A1.982 (9)C11—H11B0.9800
Cu2—N2B1.91 (2)C11—H11C0.9800
Cu1—Cu23.0251 (5)C12A—H12A0.9900
Cu2—Cu2i3.459 (5)C12A—H12B0.9900
O1—C1A1.410 (3)C12A—C13A1.558 (5)
O1—C1B1.410 (3)C13A—H13A0.9900
O2—C61.302 (4)C13A—H13B0.9900
O3—C81.359 (4)C13A—C14A1.511 (7)
O3—C111.433 (4)C14A—H14A0.9900
O4—C12A1.414 (3)C14A—H14B0.9900
O4—C12B1.414 (3)C14A—N2A1.459 (10)
O5—C171.312 (3)N2A—C15A1.293 (10)
O6—C191.362 (3)C15A—H15A0.9500
O6—C221.429 (4)C15A—C161.434 (4)
C1A—H1AA0.9900C12B—H12C0.9900
C1A—H1AB0.9900C12B—H12D0.9900
C1A—C2A1.539 (7)C12B—C13B1.462 (10)
C2A—H2AA0.9900C13B—H13C0.9900
C2A—H2AB0.9900C13B—H13D0.9900
C2A—C3A1.519 (11)C13B—C14B1.514 (16)
C3A—H3AA0.9900C14B—H14C0.9900
C3A—H3AB0.9900C14B—H14D0.9900
C3A—N1A1.473 (10)C14B—N2B1.47 (2)
N1A—C4A1.306 (9)N2B—C15B1.341 (18)
C4A—H4A0.9500C15B—H15B0.9500
C4A—C51.420 (5)C15B—C161.434 (4)
C1B—H1BA0.9900C16—C171.430 (4)
C1B—H1BB0.9900C16—C211.413 (4)
C1B—C2B1.486 (8)C17—C181.416 (4)
C2B—H2BA0.9900C18—H180.9500
C2B—H2BB0.9900C18—C191.385 (4)
C2B—C3B1.497 (12)C19—C201.410 (4)
C3B—H3BA0.9900C20—H200.9500
C3B—H3BB0.9900C20—C211.359 (4)
C3B—N1B1.497 (10)C21—H210.9500
N1B—C4B1.345 (10)C22—H22A0.9800
C4B—H4B0.9500C22—H22B0.9800
C4B—C51.420 (5)C22—H22C0.9800
C5—C61.430 (4)
O1—Cu1—Cu238.62 (6)O2—C6—C5123.2 (3)
O1—Cu1—N1A95.9 (2)O2—C6—C7118.9 (3)
O2—Cu1—Cu2130.78 (6)C7—C6—C5117.9 (3)
O2—Cu1—N1A94.7 (3)C6—C7—H7119.5
O4—Cu1—Cu238.38 (6)C8—C7—C6120.9 (3)
O4—Cu1—N1A169.7 (3)C8—C7—H7119.5
O1—Cu1—N1B95.5 (3)O3—C8—C7124.4 (3)
O2—Cu1—N1B95.0 (3)O3—C8—C9114.5 (3)
O4—Cu1—N1B167.0 (3)C7—C8—C9121.0 (3)
O2—Cu1—O1169.33 (9)C8—C9—H9120.5
O2—Cu1—O492.70 (8)C10—C9—C8118.9 (3)
O1—Cu1—O476.63 (8)C10—C9—H9120.5
N1A—Cu1—Cu2133.1 (2)C5—C10—H10118.9
N1B—Cu1—Cu2134.0 (3)C9—C10—C5122.3 (3)
O1—Cu2—Cu138.03 (6)C9—C10—H10118.9
O1—Cu2—N2A167.4 (2)O3—C11—H11A109.5
O4—Cu2—Cu138.35 (6)O3—C11—H11B109.5
O4—Cu2—N2A95.3 (3)O3—C11—H11C109.5
O5—Cu2—Cu1132.43 (6)H11A—C11—H11B109.5
O5—Cu2—N2A93.8 (3)H11A—C11—H11C109.5
N2B—Cu2—O1155.3 (4)H11B—C11—H11C109.5
N2B—Cu2—O491.4 (5)O4—C12A—H12A109.4
N2B—Cu2—O597.1 (5)O4—C12A—H12B109.4
O4—Cu2—O176.01 (8)O4—C12A—C13A111.1 (3)
O5—Cu2—O194.66 (8)H12A—C12A—H12B108.0
O5—Cu2—O4170.65 (8)C13A—C12A—H12A109.4
N2A—Cu2—Cu1133.6 (3)C13A—C12A—H12B109.4
N2B—Cu2—Cu1128.2 (5)C12A—C13A—H13A108.9
Cu1—O1—Cu2103.34 (9)C12A—C13A—H13B108.9
C1A—O1—Cu1129.45 (18)H13A—C13A—H13B107.7
C1A—O1—Cu2127.20 (18)C14A—C13A—C12A113.4 (4)
C1B—O1—Cu1129.45 (18)C14A—C13A—H13A108.9
C1B—O1—Cu2127.20 (18)C14A—C13A—H13B108.9
C6—O2—Cu1127.56 (19)C13A—C14A—H14A108.9
C8—O3—C11117.9 (3)C13A—C14A—H14B108.9
Cu1—O4—Cu2103.27 (9)H14A—C14A—H14B107.7
C12A—O4—Cu1127.22 (18)N2A—C14A—C13A113.3 (4)
C12A—O4—Cu2128.12 (18)N2A—C14A—H14A108.9
C12B—O4—Cu1127.22 (18)N2A—C14A—H14B108.9
C12B—O4—Cu2128.12 (18)C14A—N2A—Cu2120.8 (6)
C17—O5—Cu2125.17 (18)C15A—N2A—Cu2119.7 (6)
C19—O6—C22118.5 (2)C15A—N2A—C14A118.2 (7)
O1—C1A—H1AA109.3N2A—C15A—H15A116.5
O1—C1A—H1AB109.3N2A—C15A—C16126.9 (5)
O1—C1A—C2A111.5 (3)C16—C15A—H15A116.5
H1AA—C1A—H1AB108.0O4—C12B—H12C109.3
C2A—C1A—H1AA109.3O4—C12B—H12D109.3
C2A—C1A—H1AB109.3O4—C12B—C13B111.6 (4)
C1A—C2A—H2AA109.3H12C—C12B—H12D108.0
C1A—C2A—H2AB109.3C13B—C12B—H12C109.3
H2AA—C2A—H2AB108.0C13B—C12B—H12D109.3
C3A—C2A—C1A111.6 (6)C12B—C13B—H13C109.8
C3A—C2A—H2AA109.3C12B—C13B—H13D109.8
C3A—C2A—H2AB109.3C12B—C13B—C14B109.2 (8)
C2A—C3A—H3AA109.2H13C—C13B—H13D108.3
C2A—C3A—H3AB109.2C14B—C13B—H13C109.8
H3AA—C3A—H3AB107.9C14B—C13B—H13D109.8
N1A—C3A—C2A112.2 (6)C13B—C14B—H14C109.6
N1A—C3A—H3AA109.2C13B—C14B—H14D109.6
N1A—C3A—H3AB109.2H14C—C14B—H14D108.1
C3A—N1A—Cu1119.6 (6)N2B—C14B—C13B110.4 (11)
C4A—N1A—Cu1120.5 (5)N2B—C14B—H14C109.6
C4A—N1A—C3A117.8 (7)N2B—C14B—H14D109.6
N1A—C4A—H4A116.7C14B—N2B—Cu2122.8 (12)
N1A—C4A—C5126.5 (5)C15B—N2B—Cu2121.7 (12)
C5—C4A—H4A116.7C15B—N2B—C14B114.8 (14)
O1—C1B—H1BA109.2N2B—C15B—H15B117.2
O1—C1B—H1BB109.2N2B—C15B—C16125.6 (8)
O1—C1B—C2B111.9 (3)C16—C15B—H15B117.2
H1BA—C1B—H1BB107.9C17—C16—C15A123.4 (3)
C2B—C1B—H1BA109.2C17—C16—C15B123.4 (3)
C2B—C1B—H1BB109.2C21—C16—C15A116.9 (3)
C1B—C2B—H2BA108.9C21—C16—C15B116.9 (3)
C1B—C2B—H2BB108.9C21—C16—C17119.3 (3)
C1B—C2B—C3B113.5 (7)O5—C17—C16123.6 (3)
H2BA—C2B—H2BB107.7O5—C17—C18118.7 (2)
C3B—C2B—H2BA108.9C18—C17—C16117.7 (3)
C3B—C2B—H2BB108.9C17—C18—H18119.7
C2B—C3B—H3BA109.4C19—C18—C17120.7 (3)
C2B—C3B—H3BB109.4C19—C18—H18119.7
H3BA—C3B—H3BB108.0O6—C19—C18124.9 (3)
N1B—C3B—C2B111.3 (6)O6—C19—C20113.7 (3)
N1B—C3B—H3BA109.4C18—C19—C20121.4 (3)
N1B—C3B—H3BB109.4C19—C20—H20120.8
C3B—N1B—Cu1120.4 (6)C21—C20—C19118.5 (3)
C4B—N1B—Cu1119.4 (5)C21—C20—H20120.8
C4B—N1B—C3B118.6 (6)C16—C21—H21118.8
N1B—C4B—H4B116.9C20—C21—C16122.4 (3)
N1B—C4B—C5126.3 (5)C20—C21—H21118.8
C5—C4B—H4B116.9O6—C22—H22A109.5
C4A—C5—C6123.2 (3)O6—C22—H22B109.5
C4B—C5—C6123.2 (3)O6—C22—H22C109.5
C10—C5—C4A117.9 (3)H22A—C22—H22B109.5
C10—C5—C4B117.9 (3)H22A—C22—H22C109.5
C10—C5—C6118.9 (3)H22B—C22—H22C109.5
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3B—H3BB···O2ii0.992.483.385 (12)152
C11—H11B···O6iii0.982.563.359 (4)138
C12A—H12A···O20.992.512.979 (4)109
C21—H21···O6iv0.952.543.279 (4)135
C22—H22C···O2i0.982.523.362 (4)144
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1/2, z1/2; (iii) x1, y, z+1; (iv) x, y+1/2, z+1/2.
 

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