Di-μ-chloro-bis{chloro­[2-(4-methyl­phenyl­amino)-1,2-di­phenyl­ethano­ximato]copper(II)}

The title compound, [Cu₂Cl₄(C₄₂H₄₀N₄O₂)], is a binuclear mol­ecule bridged by two Cl atoms. The bridging unit Cu₂Cl₂ is almost planar and the Cu^II ions are coordinated by two N and three Cl atoms forming a square pyramid. There are two bifurcated hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.042
• wR factor = 0.098
• Data-to-parameter ratio = 21.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_213  Alert C Atom  C27    has ADP max/min Ratio ...........       3.10

PLAT_420  Alert C D-H Without Acceptor       N(4)   -   H(4)              ?


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

---

Computing details

Data collection: SMART-NT (Bruker, 1998); cell refinement: SMART-NT; data reduction: SAINT-NT (Bruker, 1998); program(s) used to solve structure: SHELXL97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

[Cu2Cl4(C42H40N4O2)]	Dx = 1.459 Mg m^−3
Mr = 901.66	Melting point = 446–448 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.8811 (5) Å	Cell parameters from 4690 reflections
b = 12.9287 (4) Å	θ = 2.4–28.1°
c = 21.7718 (6) Å	µ = 1.34 mm^−1
β = 101.569 (1)°	T = 100 K
V = 4103.6 (2) Å^3	Irregular, dark green
Z = 4	0.18 × 0.10 × 0.08 mm
F(000) = 1848

Data collection

Bruker SMART 1K diffractometer	10377 independent reflections
Radiation source: fine-focus sealed tube	6753 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.083
Detector resolution: 8 pixels mm^-1	θmax = 28.5°, θmin = 1.4°
ω scans	h = −19→19
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −17→17
Tmin = 0.709, Tmax = 0.898	l = −28→29
48138 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0342P)^2 + 2.4175P] where P = (Fo^2 + 2Fc^2)/3
10377 reflections	(Δ/σ)max = 0.001
489 parameters	Δρmax = 0.50 e Å^−3
0 restraints	Δρmin = −0.39 e Å^−3

Special details

Experimental. The data collection nominally covered full sphere of reciprocal Space, by a combination of 5 sets of ω scans each set at different φ and/or 2θ angles and each scan (25 s exposure) covering 0.3° in ω. Crystal to detector distance 4.51 cm.

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

	x	y	z	Uiso*/Ueq
Cu1	0.63458 (2)	0.61225 (3)	0.237906 (16)	0.01714 (9)
Cu2	0.85880 (2)	0.63519 (3)	0.249479 (16)	0.01648 (9)
Cl1	0.59608 (5)	0.77957 (6)	0.21876 (4)	0.02405 (17)
Cl2	0.88980 (5)	0.46601 (6)	0.27592 (3)	0.02175 (16)
Cl3	0.73930 (5)	0.64809 (5)	0.32504 (3)	0.01838 (15)
Cl4	0.75643 (5)	0.60077 (5)	0.16197 (3)	0.01840 (15)
O1	0.48024 (15)	0.63301 (17)	0.12977 (10)	0.0299 (5)
H1	0.4943	0.6937	0.1418	0.045*
O2	0.99928 (14)	0.62043 (17)	0.36662 (9)	0.0280 (5)
H2	0.9895	0.5589	0.3548	0.042*
N1	0.53513 (16)	0.56336 (19)	0.16906 (11)	0.0207 (5)
N2	0.64062 (16)	0.45796 (18)	0.25691 (10)	0.0163 (5)
H2A	0.7004	0.4368	0.2572	0.020*
N3	0.95182 (16)	0.68666 (19)	0.32129 (11)	0.0195 (5)
N4	0.84896 (16)	0.79199 (18)	0.23064 (11)	0.0174 (5)
H4	0.7910	0.8095	0.2371	0.021*
C1	0.52259 (19)	0.4664 (2)	0.15719 (13)	0.0180 (6)
C2	0.57792 (19)	0.3951 (2)	0.20629 (13)	0.0186 (6)
H2B	0.5330	0.3586	0.2273	0.022*
C3	0.9601 (2)	0.7841 (2)	0.33279 (13)	0.0199 (6)
C4	0.91349 (19)	0.8543 (2)	0.27977 (13)	0.0182 (6)
H4A	0.9626	0.8827	0.2592	0.022*
C5	0.5496 (3)	0.3491 (3)	0.49399 (17)	0.0482 (10)
H5A	0.4943	0.3865	0.4991	0.072*
H5B	0.5995	0.3638	0.5297	0.072*
H5C	0.5370	0.2746	0.4920	0.072*
C6	0.8571 (3)	0.9588 (3)	−0.01427 (16)	0.0426 (9)
H6A	0.8579	1.0343	−0.0100	0.064*
H6B	0.8030	0.9379	−0.0454	0.064*
H6C	0.9127	0.9360	−0.0280	0.064*
C7	0.45597 (19)	0.4202 (2)	0.10409 (13)	0.0199 (6)
C8	0.4305 (2)	0.4713 (3)	0.04643 (14)	0.0269 (7)
H8	0.4552	0.5375	0.0407	0.032*
C9	0.3694 (2)	0.4250 (3)	−0.00206 (15)	0.0326 (8)
H9	0.3533	0.4597	−0.0412	0.039*
C10	0.3313 (2)	0.3296 (3)	0.00514 (15)	0.0309 (8)
H10	0.2884	0.2996	−0.0283	0.037*
C11	0.3564 (2)	0.2782 (3)	0.06182 (14)	0.0263 (7)
H11	0.3310	0.2121	0.0670	0.032*
C12	0.4183 (2)	0.3221 (2)	0.11106 (14)	0.0228 (7)
H12	0.4352	0.2858	0.1496	0.027*
C13	0.6322 (2)	0.3119 (2)	0.18038 (14)	0.0202 (6)
C14	0.6895 (2)	0.3345 (3)	0.13911 (15)	0.0286 (7)
H14	0.6923	0.4031	0.1240	0.034*
C15	0.7428 (2)	0.2579 (3)	0.11967 (17)	0.0360 (9)
H15	0.7819	0.2744	0.0916	0.043*
C16	0.7391 (2)	0.1571 (3)	0.14113 (17)	0.0343 (8)
H16	0.7760	0.1048	0.1280	0.041*
C17	0.6815 (2)	0.1331 (3)	0.18165 (17)	0.0337 (8)
H17	0.6785	0.0642	0.1963	0.040*
C18	0.6280 (2)	0.2101 (2)	0.20090 (15)	0.0261 (7)
H18	0.5881	0.1931	0.2284	0.031*
C19	0.6224 (2)	0.4360 (2)	0.31895 (13)	0.0180 (6)
C20	0.6824 (2)	0.3768 (2)	0.36168 (14)	0.0267 (7)
H20	0.7388	0.3541	0.3521	0.032*
C21	0.6596 (3)	0.3507 (3)	0.41878 (15)	0.0349 (8)
H21	0.7009	0.3099	0.4480	0.042*
C22	0.5773 (2)	0.3836 (3)	0.43376 (15)	0.0312 (8)
C23	0.5203 (2)	0.4475 (3)	0.39143 (15)	0.0281 (7)
H23	0.4657	0.4741	0.4017	0.034*
C24	0.5425 (2)	0.4727 (2)	0.33446 (14)	0.0243 (7)
H24	0.5025	0.5156	0.3058	0.029*
C25	1.0125 (2)	0.8323 (2)	0.39076 (14)	0.0235 (7)
C26	1.0015 (3)	0.7972 (3)	0.44984 (16)	0.0491 (12)
H26	0.9630	0.7396	0.4530	0.059*
C27	1.0466 (4)	0.8467 (4)	0.50311 (18)	0.0738 (17)
H27	1.0396	0.8226	0.5431	0.089*
C28	1.1021 (4)	0.9314 (3)	0.49898 (18)	0.0650 (15)
H28	1.1321	0.9657	0.5360	0.078*
C29	1.1138 (3)	0.9662 (3)	0.44111 (16)	0.0376 (9)
H29	1.1528	1.0235	0.4384	0.045*
C30	1.0685 (2)	0.9174 (2)	0.38710 (14)	0.0236 (7)
H30	1.0757	0.9421	0.3473	0.028*
C31	0.86416 (19)	0.9463 (2)	0.30173 (14)	0.0203 (6)
C32	0.7933 (2)	0.9301 (2)	0.33354 (15)	0.0270 (7)
H32	0.7760	0.8618	0.3424	0.032*
C33	0.7477 (2)	1.0148 (3)	0.35241 (16)	0.0321 (8)
H33	0.6989	1.0040	0.3739	0.039*
C34	0.7729 (2)	1.1142 (3)	0.34012 (16)	0.0316 (8)
H34	0.7415	1.1714	0.3534	0.038*
C35	0.8434 (2)	1.1311 (3)	0.30852 (16)	0.0322 (8)
H35	0.8605	1.1996	0.3002	0.039*
C36	0.8894 (2)	1.0468 (2)	0.28894 (15)	0.0246 (7)
H36	0.9376	1.0579	0.2670	0.030*
C37	0.8488 (2)	0.8288 (2)	0.16733 (14)	0.0198 (6)
C38	0.9287 (2)	0.8232 (2)	0.14369 (14)	0.0230 (7)
H38	0.9820	0.7915	0.1676	0.028*
C39	0.9302 (2)	0.8642 (3)	0.08478 (14)	0.0277 (7)
H39	0.9853	0.8608	0.0692	0.033*
C40	0.8534 (2)	0.9097 (2)	0.04829 (14)	0.0272 (7)
C41	0.7731 (2)	0.9104 (2)	0.07168 (14)	0.0265 (7)
H41	0.7189	0.9386	0.0467	0.032*
C42	0.7697 (2)	0.8708 (2)	0.13090 (14)	0.0226 (6)
H42	0.7142	0.8726	0.1461	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.01716 (18)	0.01540 (18)	0.01864 (18)	0.00064 (14)	0.00304 (14)	−0.00126 (14)
Cu2	0.01664 (17)	0.01545 (18)	0.01659 (18)	0.00049 (14)	0.00150 (14)	−0.00168 (14)
Cl1	0.0288 (4)	0.0183 (4)	0.0260 (4)	0.0064 (3)	0.0080 (3)	−0.0003 (3)
Cl2	0.0246 (4)	0.0183 (4)	0.0229 (4)	0.0050 (3)	0.0059 (3)	0.0003 (3)
Cl3	0.0194 (3)	0.0187 (4)	0.0174 (3)	−0.0017 (3)	0.0046 (3)	−0.0039 (3)
Cl4	0.0200 (3)	0.0182 (3)	0.0165 (3)	−0.0016 (3)	0.0023 (3)	−0.0034 (3)
O1	0.0288 (12)	0.0236 (12)	0.0320 (12)	0.0048 (10)	−0.0063 (10)	0.0031 (10)
O2	0.0302 (12)	0.0254 (12)	0.0236 (11)	0.0031 (10)	−0.0059 (9)	0.0040 (10)
N1	0.0184 (12)	0.0213 (13)	0.0217 (13)	0.0022 (10)	0.0021 (10)	0.0020 (10)
N2	0.0142 (11)	0.0170 (12)	0.0164 (12)	−0.0003 (10)	0.0002 (9)	−0.0044 (10)
N3	0.0181 (13)	0.0213 (13)	0.0188 (13)	0.0014 (10)	0.0031 (10)	0.0022 (10)
N4	0.0172 (12)	0.0197 (13)	0.0155 (12)	−0.0029 (10)	0.0034 (10)	−0.0025 (10)
C1	0.0149 (14)	0.0232 (16)	0.0164 (14)	−0.0034 (12)	0.0040 (11)	−0.0009 (12)
C2	0.0185 (14)	0.0193 (15)	0.0174 (14)	−0.0025 (12)	0.0025 (11)	0.0001 (12)
C3	0.0174 (14)	0.0260 (16)	0.0168 (14)	−0.0042 (12)	0.0045 (12)	−0.0015 (12)
C4	0.0183 (14)	0.0187 (15)	0.0178 (14)	−0.0029 (12)	0.0037 (11)	−0.0037 (12)
C5	0.069 (3)	0.050 (3)	0.029 (2)	−0.006 (2)	0.017 (2)	0.0032 (18)
C6	0.062 (3)	0.039 (2)	0.0275 (19)	−0.0005 (19)	0.0119 (18)	0.0042 (16)
C7	0.0161 (14)	0.0279 (17)	0.0165 (14)	−0.0029 (12)	0.0050 (12)	−0.0012 (12)
C8	0.0256 (16)	0.0325 (18)	0.0224 (16)	−0.0093 (14)	0.0041 (13)	0.0017 (14)
C9	0.0349 (19)	0.044 (2)	0.0166 (16)	−0.0096 (16)	−0.0008 (14)	0.0061 (15)
C10	0.0265 (17)	0.042 (2)	0.0220 (17)	−0.0096 (15)	−0.0012 (14)	−0.0019 (15)
C11	0.0269 (17)	0.0314 (18)	0.0217 (16)	−0.0111 (14)	0.0075 (13)	−0.0029 (14)
C12	0.0219 (16)	0.0274 (17)	0.0188 (15)	−0.0033 (13)	0.0037 (12)	0.0018 (13)
C13	0.0190 (15)	0.0199 (15)	0.0203 (15)	−0.0023 (12)	0.0007 (12)	−0.0049 (12)
C14	0.0333 (18)	0.0222 (17)	0.0330 (18)	−0.0036 (14)	0.0131 (15)	−0.0095 (14)
C15	0.0329 (19)	0.036 (2)	0.044 (2)	−0.0065 (16)	0.0191 (17)	−0.0179 (17)
C16	0.0270 (18)	0.0238 (18)	0.050 (2)	0.0026 (14)	0.0038 (16)	−0.0185 (16)
C17	0.0343 (19)	0.0204 (17)	0.043 (2)	0.0040 (15)	0.0006 (16)	−0.0039 (15)
C18	0.0253 (17)	0.0233 (17)	0.0292 (17)	−0.0026 (13)	0.0044 (14)	−0.0004 (13)
C19	0.0246 (15)	0.0114 (13)	0.0171 (14)	−0.0039 (12)	0.0020 (12)	−0.0016 (11)
C20	0.0307 (17)	0.0209 (16)	0.0277 (17)	0.0035 (14)	0.0036 (14)	−0.0005 (13)
C21	0.048 (2)	0.0289 (19)	0.0248 (17)	0.0016 (16)	−0.0011 (16)	0.0063 (14)
C22	0.043 (2)	0.0285 (18)	0.0229 (16)	−0.0113 (16)	0.0090 (15)	−0.0057 (14)
C23	0.0278 (17)	0.0323 (19)	0.0259 (17)	−0.0073 (14)	0.0094 (14)	−0.0080 (14)
C24	0.0250 (16)	0.0237 (16)	0.0244 (16)	0.0006 (13)	0.0050 (13)	−0.0007 (13)
C25	0.0291 (17)	0.0239 (16)	0.0164 (15)	−0.0068 (14)	0.0023 (13)	−0.0027 (12)
C26	0.084 (3)	0.043 (2)	0.0198 (18)	−0.037 (2)	0.0080 (19)	−0.0031 (16)
C27	0.138 (5)	0.063 (3)	0.0186 (19)	−0.057 (3)	0.009 (2)	0.0001 (19)
C28	0.108 (4)	0.055 (3)	0.023 (2)	−0.040 (3)	−0.011 (2)	−0.0027 (19)
C29	0.042 (2)	0.039 (2)	0.0268 (18)	−0.0179 (17)	−0.0060 (16)	−0.0014 (16)
C30	0.0237 (16)	0.0268 (17)	0.0198 (15)	−0.0052 (13)	0.0027 (13)	0.0016 (13)
C31	0.0168 (14)	0.0215 (16)	0.0226 (16)	−0.0030 (12)	0.0040 (12)	−0.0095 (12)
C32	0.0295 (17)	0.0215 (16)	0.0316 (18)	−0.0074 (14)	0.0098 (14)	−0.0080 (14)
C33	0.0288 (18)	0.0328 (19)	0.037 (2)	−0.0057 (15)	0.0120 (15)	−0.0139 (16)
C34	0.0295 (18)	0.0258 (18)	0.0389 (19)	0.0045 (15)	0.0052 (15)	−0.0135 (15)
C35	0.0290 (18)	0.0237 (17)	0.042 (2)	−0.0040 (14)	0.0028 (15)	−0.0048 (15)
C36	0.0188 (15)	0.0260 (17)	0.0291 (17)	−0.0014 (13)	0.0049 (13)	−0.0010 (13)
C37	0.0243 (16)	0.0134 (14)	0.0204 (15)	−0.0037 (12)	0.0010 (12)	−0.0028 (12)
C38	0.0208 (15)	0.0250 (16)	0.0228 (16)	0.0025 (13)	0.0031 (13)	−0.0029 (13)
C39	0.0331 (18)	0.0291 (18)	0.0234 (16)	−0.0032 (15)	0.0115 (14)	−0.0047 (14)
C40	0.043 (2)	0.0194 (16)	0.0201 (16)	−0.0028 (14)	0.0073 (14)	−0.0037 (12)
C41	0.0313 (18)	0.0204 (16)	0.0246 (16)	0.0054 (13)	−0.0019 (14)	0.0001 (13)
C42	0.0274 (16)	0.0173 (15)	0.0211 (15)	0.0012 (13)	0.0002 (13)	−0.0025 (12)

Geometric parameters (Å, º)

Cu1—N1	1.987 (2)	C14—C15	1.386 (4)
Cu1—N2	2.036 (2)	C14—H14	0.9500
Cu1—Cl3	2.2485 (7)	C15—C16	1.390 (5)
Cu1—Cl1	2.2552 (8)	C15—H15	0.9500
Cu1—Cl4	2.6919 (8)	C16—C17	1.383 (5)
Cu1—Cu2	3.3087 (5)	C16—H16	0.9500
Cu2—N3	1.984 (2)	C17—C18	1.391 (4)
Cu2—N4	2.068 (2)	C17—H17	0.9500
Cu2—Cl4	2.2326 (7)	C18—H18	0.9500
Cu2—Cl2	2.2852 (8)	C19—C24	1.383 (4)
Cu2—Cl3	2.6589 (8)	C19—C20	1.384 (4)
O1—N1	1.389 (3)	C20—C21	1.394 (5)
O1—H1	0.8400	C20—H20	0.9500
O2—N3	1.388 (3)	C21—C22	1.395 (5)
O2—H2	0.8400	C21—H21	0.9500
N1—C1	1.286 (4)	C22—C23	1.393 (5)
N2—C19	1.458 (4)	C23—C24	1.385 (4)
N2—C2	1.527 (3)	C23—H23	0.9500
N2—H2A	0.9300	C24—H24	0.9500
N3—C3	1.285 (4)	C25—C30	1.391 (4)
N4—C37	1.458 (4)	C25—C26	1.404 (4)
N4—C4	1.518 (3)	C26—C27	1.376 (5)
N4—H4	0.9300	C26—H26	0.9500
C1—C7	1.489 (4)	C27—C28	1.386 (6)
C1—C2	1.522 (4)	C27—H27	0.9500
C2—C13	1.520 (4)	C28—C29	1.381 (5)
C2—H2B	1.0000	C28—H28	0.9500
C3—C25	1.482 (4)	C29—C30	1.385 (4)
C3—C4	1.522 (4)	C29—H29	0.9500
C4—C31	1.524 (4)	C30—H30	0.9500
C4—H4A	1.0000	C31—C32	1.389 (4)
C5—C22	1.519 (5)	C31—C36	1.396 (4)
C5—H5A	0.9800	C32—C33	1.392 (4)
C5—H5B	0.9800	C32—H32	0.9500
C5—H5C	0.9800	C33—C34	1.380 (5)
C6—C40	1.514 (4)	C33—H33	0.9500
C6—H6A	0.9800	C34—C35	1.383 (5)
C6—H6B	0.9800	C34—H34	0.9500
C6—H6C	0.9800	C35—C36	1.397 (4)
C7—C8	1.402 (4)	C35—H35	0.9500
C7—C12	1.408 (4)	C36—H36	0.9500
C8—C9	1.384 (4)	C37—C38	1.389 (4)
C8—H8	0.9500	C37—C42	1.391 (4)
C9—C10	1.379 (5)	C38—C39	1.392 (4)
C9—H9	0.9500	C38—H38	0.9500
C10—C11	1.386 (4)	C39—C40	1.385 (5)
C10—H10	0.9500	C39—H39	0.9500
C11—C12	1.386 (4)	C40—C41	1.389 (5)
C11—H11	0.9500	C41—C42	1.397 (4)
C12—H12	0.9500	C41—H41	0.9500
C13—C14	1.389 (4)	C42—H42	0.9500
C13—C18	1.396 (4)
N1—Cu1—N2	80.65 (10)	C12—C11—H11	119.6
N1—Cu1—Cl3	170.92 (8)	C11—C12—C7	120.2 (3)
N2—Cu1—Cl3	92.04 (7)	C11—C12—H12	119.9
N1—Cu1—Cl1	92.44 (8)	C7—C12—H12	119.9
N2—Cu1—Cl1	167.64 (7)	C14—C13—C18	118.5 (3)
Cl3—Cu1—Cl1	93.76 (3)	C14—C13—C2	122.2 (3)
N1—Cu1—Cl4	90.61 (7)	C18—C13—C2	119.2 (3)
N2—Cu1—Cl4	93.62 (7)	C15—C14—C13	120.7 (3)
Cl3—Cu1—Cl4	95.24 (3)	C15—C14—H14	119.7
Cl1—Cu1—Cl4	96.71 (3)	C13—C14—H14	119.7
N1—Cu1—Cu2	132.32 (7)	C14—C15—C16	120.3 (3)
N2—Cu1—Cu2	93.99 (7)	C14—C15—H15	119.9
Cl3—Cu1—Cu2	53.10 (2)	C16—C15—H15	119.9
Cl1—Cu1—Cu2	98.22 (2)	C17—C16—C15	119.7 (3)
N3—Cu2—N4	80.68 (9)	C17—C16—H16	120.1
N3—Cu2—Cl4	171.22 (7)	C15—C16—H16	120.1
N4—Cu2—Cl4	90.98 (7)	C16—C17—C18	119.8 (3)
N3—Cu2—Cl2	92.80 (7)	C16—C17—H17	120.1
N4—Cu2—Cl2	172.36 (7)	C18—C17—H17	120.1
Cl4—Cu2—Cl2	95.33 (3)	C17—C18—C13	120.9 (3)
N3—Cu2—Cl3	86.50 (7)	C17—C18—H18	119.5
N4—Cu2—Cl3	91.82 (7)	C13—C18—H18	119.5
Cl4—Cu2—Cl3	96.54 (3)	C24—C19—C20	119.8 (3)
Cl2—Cu2—Cl3	91.75 (3)	C24—C19—N2	119.2 (3)
N3—Cu2—Cu1	128.59 (7)	C20—C19—N2	121.0 (3)
N4—Cu2—Cu1	92.44 (7)	C19—C20—C21	119.6 (3)
Cl4—Cu2—Cu1	53.99 (2)	C19—C20—H20	120.2
Cl2—Cu2—Cu1	94.76 (2)	C21—C20—H20	120.2
Cu1—Cl3—Cu2	84.34 (2)	C20—C21—C22	121.1 (3)
Cu2—Cl4—Cu1	83.87 (2)	C20—C21—H21	119.4
N1—O1—H1	109.5	C22—C21—H21	119.4
N3—O2—H2	109.5	C23—C22—C21	118.2 (3)
C1—N1—O1	117.7 (2)	C23—C22—C5	120.7 (3)
C1—N1—Cu1	121.2 (2)	C21—C22—C5	121.1 (3)
O1—N1—Cu1	121.03 (18)	C24—C23—C22	120.6 (3)
C19—N2—C2	111.4 (2)	C24—C23—H23	119.7
C19—N2—Cu1	111.73 (17)	C22—C23—H23	119.7
C2—N2—Cu1	112.26 (17)	C19—C24—C23	120.6 (3)
C19—N2—H2A	107.0	C19—C24—H24	119.7
C2—N2—H2A	107.0	C23—C24—H24	119.7
Cu1—N2—H2A	107.0	C30—C25—C26	119.3 (3)
C3—N3—O2	116.8 (2)	C30—C25—C3	120.2 (3)
C3—N3—Cu2	120.5 (2)	C26—C25—C3	120.4 (3)
O2—N3—Cu2	121.92 (18)	C27—C26—C25	119.7 (3)
C37—N4—C4	112.0 (2)	C27—C26—H26	120.2
C37—N4—Cu2	119.62 (18)	C25—C26—H26	120.2
C4—N4—Cu2	111.78 (17)	C26—C27—C28	120.6 (4)
C37—N4—H4	103.8	C26—C27—H27	119.7
C4—N4—H4	103.8	C28—C27—H27	119.7
Cu2—N4—H4	103.8	C29—C28—C27	120.2 (4)
N1—C1—C7	126.5 (3)	C29—C28—H28	119.9
N1—C1—C2	114.4 (2)	C27—C28—H28	119.9
C7—C1—C2	119.0 (3)	C28—C29—C30	119.8 (3)
C13—C2—C1	114.9 (2)	C28—C29—H29	120.1
C13—C2—N2	110.6 (2)	C30—C29—H29	120.1
C1—C2—N2	110.5 (2)	C29—C30—C25	120.5 (3)
C13—C2—H2B	106.8	C29—C30—H30	119.8
C1—C2—H2B	106.8	C25—C30—H30	119.8
N2—C2—H2B	106.8	C32—C31—C36	120.1 (3)
N3—C3—C25	126.3 (3)	C32—C31—C4	120.0 (3)
N3—C3—C4	115.2 (2)	C36—C31—C4	119.9 (3)
C25—C3—C4	118.5 (3)	C31—C32—C33	119.5 (3)
N4—C4—C3	110.2 (2)	C31—C32—H32	120.2
N4—C4—C31	111.0 (2)	C33—C32—H32	120.2
C3—C4—C31	113.7 (2)	C34—C33—C32	120.5 (3)
N4—C4—H4A	107.2	C34—C33—H33	119.7
C3—C4—H4A	107.2	C32—C33—H33	119.7
C31—C4—H4A	107.2	C33—C34—C35	120.4 (3)
C22—C5—H5A	109.5	C33—C34—H34	119.8
C22—C5—H5B	109.5	C35—C34—H34	119.8
H5A—C5—H5B	109.5	C34—C35—C36	119.8 (3)
C22—C5—H5C	109.5	C34—C35—H35	120.1
H5A—C5—H5C	109.5	C36—C35—H35	120.1
H5B—C5—H5C	109.5	C31—C36—C35	119.8 (3)
C40—C6—H6A	109.5	C31—C36—H36	120.1
C40—C6—H6B	109.5	C35—C36—H36	120.1
H6A—C6—H6B	109.5	C38—C37—C42	119.9 (3)
C40—C6—H6C	109.5	C38—C37—N4	119.6 (3)
H6A—C6—H6C	109.5	C42—C37—N4	120.5 (3)
H6B—C6—H6C	109.5	C37—C38—C39	119.6 (3)
C8—C7—C12	118.6 (3)	C37—C38—H38	120.2
C8—C7—C1	121.7 (3)	C39—C38—H38	120.2
C12—C7—C1	119.7 (3)	C40—C39—C38	121.8 (3)
C9—C8—C7	119.8 (3)	C40—C39—H39	119.1
C9—C8—H8	120.1	C38—C39—H39	119.1
C7—C8—H8	120.1	C39—C40—C41	117.6 (3)
C10—C9—C8	121.5 (3)	C39—C40—C6	121.3 (3)
C10—C9—H9	119.3	C41—C40—C6	121.1 (3)
C8—C9—H9	119.3	C40—C41—C42	121.9 (3)
C9—C10—C11	119.1 (3)	C40—C41—H41	119.1
C9—C10—H10	120.4	C42—C41—H41	119.1
C11—C10—H10	120.4	C37—C42—C41	119.1 (3)
C10—C11—C12	120.7 (3)	C37—C42—H42	120.4
C10—C11—H11	119.6	C41—C42—H42	120.4

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl1	0.84	2.31	2.996 (2)	140
O2—H2···Cl2	0.84	2.36	3.041 (2)	139
N2—H2A···Cl2	0.93	2.79	3.649 (2)	154
N4—H4···Cl1	0.93	2.87	3.723 (3)	153