Aqua­[tris­(1H-benzimidazol-2-ylmeth­yl)amine]copper(II) bis­(perchlorate) 4-nitro­pyridine N-oxide monohydrate

In the title structure, [Cu(C₂₄H₂₁N₇)(H₂O)](ClO₄)₂·C₅H₄N₂O₃·H₂O, the Cu^II atom is bonded to a tris­(1H-benzimidazol-2-ylmeth­yl)amine (ntb) ligand and a water mol­ecule through four N atoms and one O atom, giving a distorted trigonal–bipyramidal coordination geometry with approximate C₃ mol­ecular symmetry.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in solvent or counterion
• R factor = 0.045
• wR factor = 0.131
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................       8.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Aqua[tris(1H-benzimidazol-2-ylmethyl)amine]copper(II) bis(perchlorate) 4-nitropyridine N-oxide monohydrate

Crystal data

[Cu(C24H21N7)(H2O)](ClO4)2·C5H4N2O3·H2O	F(000) = 1732
Mr = 846.05	Dx = 1.506 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2202 reflections
a = 11.986 (3) Å	θ = 2.3–18.3°
b = 24.134 (6) Å	µ = 0.80 mm^−1
c = 14.226 (3) Å	T = 298 K
β = 114.913 (1)°	Tetragonal, blue–green
V = 3732.2 (15) Å^3	0.3 × 0.2 × 0.2 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	7345 independent reflections
Radiation source: sealed tube	5401 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.012
φ and ω scans	θmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −14→13
Tmin = 0.83, Tmax = 0.85	k = −29→29
19956 measured reflections	l = −10→17

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.07P)^2 + 1.99P] where P = (Fo^2 + 2Fc^2)/3
7345 reflections	(Δ/σ)max = 0.001
496 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.34 e Å^−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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.83019 (4)	0.094445 (16)	0.22742 (3)	0.04919 (13)
C1	1.0004 (3)	0.10272 (13)	0.1308 (3)	0.0492 (7)
H1A	0.9444	0.1151	0.0621	0.059*
H1B	1.0763	0.0907	0.1284	0.059*
C2	1.0250 (3)	0.14840 (13)	0.2069 (3)	0.0502 (7)
C3	1.0995 (3)	0.22140 (13)	0.2990 (3)	0.0496 (7)
C4	1.1653 (3)	0.26896 (13)	0.3482 (3)	0.0524 (8)
H4	1.2283	0.2836	0.3338	0.063*
C5	1.1287 (3)	0.29296 (14)	0.4211 (3)	0.0531 (8)
H5	1.1699	0.3245	0.4563	0.064*
C6	1.0365 (3)	0.27249 (13)	0.4426 (3)	0.0505 (7)
H6	1.0175	0.2905	0.4918	0.061*
C7	0.9686 (3)	0.22508 (13)	0.3935 (2)	0.0497 (7)
H7	0.9060	0.2109	0.4087	0.060*
C8	1.0031 (3)	0.20073 (13)	0.3192 (3)	0.0500 (7)
C9	1.0350 (3)	0.02368 (14)	0.2476 (2)	0.0496 (7)
H9A	1.1034	0.0467	0.2918	0.060*
H9B	1.0666	−0.0054	0.2185	0.060*
C10	0.9721 (3)	−0.00100 (13)	0.3092 (3)	0.0498 (7)
C11	0.9208 (3)	−0.05591 (13)	0.4090 (3)	0.0503 (7)
C12	0.9092 (3)	−0.09852 (13)	0.4715 (3)	0.0500 (7)
H12	0.9609	−0.1292	0.4907	0.060*
C13	0.8167 (3)	−0.09151 (13)	0.5015 (3)	0.0500 (7)
H13	0.8063	−0.1181	0.5445	0.060*
C14	0.7371 (3)	−0.04691 (13)	0.4717 (3)	0.0499 (7)
H14	0.6736	−0.0448	0.4928	0.060*
C15	0.7509 (3)	−0.00581 (13)	0.4113 (2)	0.0494 (7)
H15	0.6985	0.0246	0.3919	0.059*
C16	0.8447 (3)	−0.01069 (13)	0.3797 (2)	0.0487 (7)
C17	0.8665 (3)	0.02224 (14)	0.0746 (2)	0.0502 (7)
H17A	0.8979	0.0237	0.0220	0.060*
H17B	0.8683	−0.0160	0.0961	0.060*
C18	0.7414 (3)	0.04272 (13)	0.0322 (3)	0.0502 (7)
C19	0.5445 (3)	0.05339 (13)	−0.0687 (3)	0.0504 (8)
C20	0.4297 (3)	0.05198 (13)	−0.1446 (3)	0.0513 (8)
H20	0.4117	0.0343	−0.2074	0.062*
C21	0.3428 (3)	0.07755 (13)	−0.1246 (3)	0.0512 (8)
H21	0.2635	0.0789	−0.1772	0.061*
C22	0.3640 (3)	0.10256 (13)	−0.0290 (3)	0.0526 (8)
H22	0.2994	0.1178	−0.0178	0.063*
C23	0.4822 (3)	0.10389 (13)	0.0473 (3)	0.0493 (7)
H23	0.5003	0.1209	0.1107	0.059*
C24	0.5732 (3)	0.07897 (13)	0.0264 (3)	0.0495 (7)
C25	0.1180 (3)	0.31296 (14)	−0.0127 (3)	0.0534 (8)
H25	0.1348	0.2893	−0.0567	0.064*
C26	0.0274 (3)	0.29844 (14)	0.0260 (3)	0.0525 (8)
H26	−0.0142	0.2649	0.0061	0.063*
C27	0.0028 (3)	0.33096 (14)	0.0874 (3)	0.0504 (7)
C28	0.0620 (3)	0.38066 (14)	0.1136 (3)	0.0517 (8)
H28	0.0457	0.4043	0.1579	0.062*
C29	0.1454 (3)	0.39653 (14)	0.0757 (3)	0.0516 (8)
H29	0.1799	0.4317	0.0908	0.062*
Cl1	0.44589 (7)	0.36690 (3)	0.34986 (6)	0.0511 (2)
Cl2	0.37923 (7)	0.06048 (3)	0.28900 (6)	0.0510 (2)
N1	0.9449 (2)	0.05686 (11)	0.1651 (2)	0.0495 (6)
N2	1.1105 (3)	0.18768 (11)	0.2300 (2)	0.0510 (6)
H2A	1.1637	0.1907	0.2044	0.061*
N3	0.9567 (3)	0.15369 (11)	0.2598 (2)	0.0496 (6)
N4	1.0030 (3)	−0.04871 (11)	0.3636 (2)	0.0505 (6)
H4A	1.0622	−0.0706	0.3694	0.061*
N5	0.8792 (2)	0.02263 (11)	0.3171 (2)	0.0494 (6)
N6	0.6525 (2)	0.03097 (11)	−0.0619 (2)	0.0500 (6)
H6A	0.6620	0.0125	−0.1097	0.060*
N7	0.6983 (2)	0.07284 (11)	0.0873 (2)	0.0480 (6)
N8	0.1777 (3)	0.36253 (11)	0.0176 (2)	0.0519 (7)
N9	−0.0860 (3)	0.31258 (12)	0.1274 (2)	0.0518 (6)
O1	0.7263 (2)	0.13333 (9)	0.28148 (17)	0.0506 (5)
H1C	0.6686	0.1120	0.2789	0.061*
H1E	0.7680	0.1427	0.3416	0.076*
O2	0.2629 (2)	0.37474 (9)	−0.01072 (17)	0.0529 (5)
O3	−0.1010 (2)	0.34446 (9)	0.18782 (18)	0.0533 (5)
O4	−0.1364 (2)	0.26834 (9)	0.10153 (17)	0.0531 (5)
O11	0.5515 (2)	0.39237 (9)	0.38205 (18)	0.0543 (6)
O12	0.3627 (2)	0.39921 (9)	0.37103 (18)	0.0546 (6)
O13	0.4557 (2)	0.31990 (9)	0.40061 (18)	0.0544 (6)
O14	0.4008 (2)	0.35953 (9)	0.24250 (17)	0.0522 (5)
O21	0.4749 (2)	0.08843 (9)	0.28632 (18)	0.0540 (5)
O22	0.3181 (2)	0.09427 (9)	0.33445 (18)	0.0534 (5)
O23	0.4000 (2)	0.01233 (9)	0.33904 (18)	0.0563 (6)
O24	0.2940 (2)	0.05351 (9)	0.18847 (18)	0.0554 (6)
O1W	0.6902 (4)	0.23966 (17)	0.2085 (3)	0.0492 (10)	0.50
H1WD	0.6167	0.2295	0.1933	0.059*	0.50
H1WC	0.7360	0.2300	0.2703	0.059*	0.50
O2W	0.3066 (4)	0.20177 (18)	0.1613 (4)	0.0552 (11)	0.50
H2WD	0.3343	0.2239	0.2125	0.066*	0.50
H2WC	0.3505	0.2040	0.1276	0.066*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0495 (2)	0.0501 (2)	0.0489 (2)	−0.00018 (17)	0.02158 (18)	−0.00109 (17)
C1	0.0527 (18)	0.0499 (17)	0.0483 (18)	0.0014 (14)	0.0244 (14)	−0.0023 (14)
C2	0.0521 (19)	0.0494 (17)	0.0484 (18)	−0.0014 (14)	0.0205 (15)	−0.0014 (14)
C3	0.0485 (18)	0.0504 (18)	0.0487 (18)	−0.0004 (14)	0.0193 (14)	−0.0003 (14)
C4	0.0508 (19)	0.0493 (17)	0.055 (2)	−0.0036 (14)	0.0203 (15)	−0.0011 (15)
C5	0.0541 (19)	0.0500 (18)	0.0517 (19)	−0.0012 (15)	0.0188 (15)	−0.0005 (14)
C6	0.0495 (18)	0.0490 (17)	0.0521 (18)	−0.0004 (14)	0.0205 (15)	−0.0037 (14)
C7	0.0502 (18)	0.0502 (18)	0.0491 (18)	−0.0015 (14)	0.0213 (15)	0.0009 (14)
C8	0.0492 (18)	0.0486 (17)	0.0526 (18)	0.0025 (14)	0.0218 (15)	0.0012 (14)
C9	0.0489 (18)	0.0517 (18)	0.0491 (17)	0.0015 (14)	0.0215 (14)	−0.0029 (14)
C10	0.0496 (18)	0.0497 (17)	0.0504 (18)	−0.0016 (14)	0.0214 (15)	0.0003 (14)
C11	0.0504 (18)	0.0522 (18)	0.0486 (18)	0.0014 (14)	0.0212 (15)	−0.0018 (14)
C12	0.0512 (18)	0.0482 (17)	0.0488 (18)	0.0006 (14)	0.0192 (15)	−0.0009 (14)
C13	0.0490 (18)	0.0509 (18)	0.0503 (18)	−0.0020 (14)	0.0210 (14)	−0.0024 (14)
C14	0.0500 (18)	0.0510 (18)	0.0503 (18)	−0.0028 (14)	0.0228 (15)	−0.0008 (14)
C15	0.0503 (18)	0.0479 (17)	0.0488 (18)	0.0008 (14)	0.0197 (14)	0.0002 (14)
C16	0.0501 (18)	0.0496 (17)	0.0451 (17)	0.0003 (14)	0.0190 (14)	−0.0012 (14)
C17	0.0508 (18)	0.0520 (18)	0.0494 (18)	0.0003 (14)	0.0226 (14)	−0.0022 (14)
C18	0.0527 (19)	0.0474 (17)	0.0492 (18)	0.0013 (14)	0.0202 (15)	0.0004 (14)
C19	0.0512 (19)	0.0495 (17)	0.0468 (18)	0.0005 (14)	0.0171 (14)	−0.0018 (14)
C20	0.0530 (19)	0.0487 (17)	0.0506 (19)	−0.0011 (14)	0.0204 (15)	0.0011 (14)
C21	0.0475 (18)	0.0514 (17)	0.0544 (19)	−0.0011 (14)	0.0211 (15)	0.0005 (14)
C22	0.0516 (19)	0.0518 (18)	0.0528 (19)	0.0009 (14)	0.0203 (15)	0.0027 (15)
C23	0.0468 (18)	0.0511 (18)	0.0504 (18)	−0.0023 (14)	0.0208 (14)	0.0018 (14)
C24	0.0517 (19)	0.0468 (17)	0.0521 (19)	−0.0011 (14)	0.0239 (15)	0.0018 (14)
C25	0.0535 (19)	0.0519 (18)	0.0548 (19)	0.0010 (15)	0.0229 (16)	−0.0024 (15)
C26	0.0556 (19)	0.0525 (18)	0.0491 (18)	−0.0020 (15)	0.0218 (15)	−0.0020 (15)
C27	0.0526 (19)	0.0510 (18)	0.0472 (18)	−0.0012 (14)	0.0205 (15)	−0.0018 (14)
C28	0.0520 (19)	0.0492 (18)	0.0520 (19)	0.0011 (14)	0.0200 (15)	0.0006 (15)
C29	0.0524 (19)	0.0513 (18)	0.0499 (18)	−0.0034 (15)	0.0204 (15)	−0.0013 (14)
Cl1	0.0519 (5)	0.0502 (4)	0.0518 (4)	−0.0020 (3)	0.0223 (4)	0.0000 (3)
Cl2	0.0510 (4)	0.0521 (4)	0.0512 (5)	0.0003 (3)	0.0226 (4)	−0.0002 (3)
N1	0.0493 (15)	0.0505 (15)	0.0501 (15)	−0.0015 (12)	0.0224 (12)	−0.0027 (12)
N2	0.0528 (16)	0.0518 (15)	0.0487 (15)	−0.0008 (12)	0.0215 (13)	−0.0006 (12)
N3	0.0524 (15)	0.0500 (15)	0.0467 (15)	−0.0010 (12)	0.0212 (12)	−0.0012 (12)
N4	0.0492 (15)	0.0504 (15)	0.0512 (15)	−0.0007 (12)	0.0203 (12)	−0.0016 (12)
N5	0.0500 (15)	0.0503 (14)	0.0480 (15)	−0.0011 (12)	0.0206 (12)	−0.0005 (12)
N6	0.0501 (15)	0.0512 (15)	0.0480 (15)	−0.0037 (12)	0.0199 (12)	−0.0017 (12)
N7	0.0482 (15)	0.0469 (14)	0.0500 (15)	−0.0008 (12)	0.0217 (12)	−0.0015 (12)
N8	0.0547 (16)	0.0512 (15)	0.0514 (16)	−0.0009 (12)	0.0238 (13)	0.0006 (12)
N9	0.0507 (16)	0.0554 (16)	0.0486 (15)	0.0016 (13)	0.0204 (13)	0.0028 (13)
O1	0.0496 (13)	0.0529 (12)	0.0508 (13)	−0.0017 (10)	0.0226 (10)	−0.0023 (10)
O2	0.0521 (13)	0.0542 (13)	0.0531 (13)	0.0000 (10)	0.0228 (11)	0.0004 (10)
O3	0.0557 (14)	0.0517 (13)	0.0522 (13)	0.0009 (10)	0.0224 (11)	0.0007 (10)
O4	0.0554 (13)	0.0525 (13)	0.0500 (13)	−0.0010 (11)	0.0208 (11)	0.0006 (10)
O11	0.0521 (13)	0.0538 (13)	0.0548 (13)	0.0000 (10)	0.0203 (11)	0.0026 (10)
O12	0.0555 (14)	0.0536 (13)	0.0535 (13)	0.0018 (10)	0.0217 (11)	−0.0002 (10)
O13	0.0555 (14)	0.0524 (13)	0.0533 (13)	0.0008 (10)	0.0211 (11)	0.0013 (10)
O14	0.0520 (13)	0.0528 (12)	0.0500 (13)	0.0021 (10)	0.0198 (10)	0.0010 (10)
O21	0.0533 (13)	0.0544 (13)	0.0538 (13)	−0.0022 (10)	0.0222 (11)	0.0020 (10)
O22	0.0551 (13)	0.0513 (12)	0.0554 (13)	0.0003 (10)	0.0249 (11)	−0.0035 (10)
O23	0.0576 (14)	0.0531 (13)	0.0600 (14)	0.0015 (11)	0.0264 (11)	0.0002 (11)
O24	0.0543 (14)	0.0555 (13)	0.0557 (14)	−0.0007 (10)	0.0226 (11)	−0.0019 (11)
O1W	0.045 (2)	0.050 (2)	0.053 (3)	−0.0003 (19)	0.021 (2)	0.003 (2)
O2W	0.055 (3)	0.055 (3)	0.057 (3)	0.002 (2)	0.025 (2)	0.005 (2)

Geometric parameters (Å, º)

Cu1—O1	1.957 (2)	C18—N7	1.323 (4)
Cu1—N3	1.992 (3)	C18—N6	1.344 (4)
Cu1—N7	2.023 (3)	C19—C20	1.345 (5)
Cu1—N5	2.085 (3)	C19—N6	1.369 (4)
Cu1—N1	2.127 (3)	C19—C24	1.392 (5)
C1—N1	1.476 (4)	C20—C21	1.340 (5)
C1—C2	1.485 (4)	C20—H20	0.9300
C1—H1A	0.9700	C21—C22	1.410 (5)
C1—H1B	0.9700	C21—H21	0.9300
C2—N2	1.332 (4)	C22—C23	1.376 (5)
C2—N3	1.332 (4)	C22—H22	0.9300
C3—N2	1.325 (4)	C23—C24	1.383 (5)
C3—C8	1.396 (5)	C23—H23	0.9300
C3—C4	1.401 (4)	C24—N7	1.387 (4)
C4—C5	1.410 (5)	C25—N8	1.367 (4)
C4—H4	0.9300	C25—C26	1.452 (5)
C5—C6	1.358 (5)	C25—H25	0.9300
C5—H5	0.9300	C26—C27	1.298 (4)
C6—C7	1.407 (4)	C26—H26	0.9300
C6—H6	0.9300	C27—C28	1.363 (5)
C7—C8	1.415 (5)	C27—N9	1.470 (4)
C7—H7	0.9300	C28—C29	1.375 (5)
C8—N3	1.385 (4)	C28—H28	0.9300
C9—N1	1.455 (4)	C29—N8	1.332 (4)
C9—C10	1.499 (5)	C29—H29	0.9300
C9—H9A	0.9700	Cl1—O11	1.305 (2)
C9—H9B	0.9700	Cl1—O13	1.323 (2)
C10—N5	1.297 (4)	Cl1—O12	1.395 (2)
C10—N4	1.350 (4)	Cl1—O14	1.400 (2)
C11—C16	1.370 (4)	Cl2—O23	1.330 (2)
C11—N4	1.398 (4)	Cl2—O21	1.345 (2)
C11—C12	1.403 (5)	Cl2—O24	1.373 (2)
C12—C13	1.357 (5)	Cl2—O22	1.421 (2)
C12—H12	0.9300	N2—H2A	0.8600
C13—C14	1.381 (5)	N4—H4A	0.8600
C13—H13	0.9300	N6—H6A	0.8600
C14—C15	1.368 (4)	N8—O2	1.281 (3)
C14—H14	0.9300	N9—O4	1.206 (3)
C15—C16	1.380 (5)	N9—O3	1.221 (3)
C15—H15	0.9300	O1—H1C	0.8500
C16—N5	1.386 (4)	O1—H1E	0.8200
C17—C18	1.447 (5)	O1W—H1WD	0.8500
C17—N1	1.491 (4)	O1W—H1WC	0.8501
C17—H17A	0.9700	O2W—H2WD	0.8501
C17—H17B	0.9700	O2W—H2WC	0.8500
O1—Cu1—N3	96.50 (10)	C21—C20—H20	121.9
O1—Cu1—N7	98.53 (10)	C19—C20—H20	121.9
N3—Cu1—N7	128.01 (11)	C20—C21—C22	124.2 (3)
O1—Cu1—N5	102.72 (10)	C20—C21—H21	117.9
N3—Cu1—N5	117.68 (11)	C22—C21—H21	117.9
N7—Cu1—N5	106.90 (11)	C23—C22—C21	118.6 (3)
O1—Cu1—N1	176.53 (10)	C23—C22—H22	120.7
N3—Cu1—N1	80.78 (11)	C21—C22—H22	120.7
N7—Cu1—N1	81.59 (11)	C22—C23—C24	117.6 (3)
N5—Cu1—N1	80.52 (11)	C22—C23—H23	121.2
N1—C1—C2	107.1 (3)	C24—C23—H23	121.2
N1—C1—H1A	110.3	C23—C24—N7	130.9 (3)
C2—C1—H1A	110.3	C23—C24—C19	120.5 (3)
N1—C1—H1B	110.3	N7—C24—C19	108.6 (3)
C2—C1—H1B	110.3	N8—C25—C26	117.9 (3)
H1A—C1—H1B	108.5	N8—C25—H25	121.1
N2—C2—N3	112.6 (3)	C26—C25—H25	121.1
N2—C2—C1	127.2 (3)	C27—C26—C25	121.9 (3)
N3—C2—C1	120.2 (3)	C27—C26—H26	119.1
N2—C3—C8	106.4 (3)	C25—C26—H26	119.1
N2—C3—C4	131.5 (3)	C26—C27—C28	118.4 (3)
C8—C3—C4	122.1 (3)	C26—C27—N9	119.0 (3)
C3—C4—C5	114.8 (3)	C28—C27—N9	122.6 (3)
C3—C4—H4	122.6	C27—C28—C29	121.3 (3)
C5—C4—H4	122.6	C27—C28—H28	119.4
C6—C5—C4	123.5 (3)	C29—C28—H28	119.4
C6—C5—H5	118.3	N8—C29—C28	121.4 (3)
C4—C5—H5	118.3	N8—C29—H29	119.3
C5—C6—C7	122.6 (3)	C28—C29—H29	119.3
C5—C6—H6	118.7	O11—Cl1—O13	111.25 (15)
C7—C6—H6	118.7	O11—Cl1—O12	109.69 (15)
C6—C7—C8	114.8 (3)	O13—Cl1—O12	105.59 (15)
C6—C7—H7	122.6	O11—Cl1—O14	108.31 (15)
C8—C7—H7	122.6	O13—Cl1—O14	113.03 (14)
N3—C8—C3	108.8 (3)	O12—Cl1—O14	108.91 (14)
N3—C8—C7	128.9 (3)	O23—Cl2—O21	118.95 (15)
C3—C8—C7	122.2 (3)	O23—Cl2—O24	109.86 (15)
N1—C9—C10	107.7 (3)	O21—Cl2—O24	107.51 (15)
N1—C9—H9A	110.2	O23—Cl2—O22	105.89 (15)
C10—C9—H9A	110.2	O21—Cl2—O22	109.55 (15)
N1—C9—H9B	110.2	O24—Cl2—O22	104.12 (15)
C10—C9—H9B	110.2	C9—N1—C1	113.3 (3)
H9A—C9—H9B	108.5	C9—N1—C17	111.9 (2)
N5—C10—N4	111.3 (3)	C1—N1—C17	110.0 (3)
N5—C10—C9	122.5 (3)	C9—N1—Cu1	106.8 (2)
N4—C10—C9	126.2 (3)	C1—N1—Cu1	106.16 (19)
C16—C11—N4	105.6 (3)	C17—N1—Cu1	108.41 (19)
C16—C11—C12	123.1 (3)	C3—N2—C2	108.3 (3)
N4—C11—C12	131.3 (3)	C3—N2—H2A	125.9
C13—C12—C11	114.9 (3)	C2—N2—H2A	125.9
C13—C12—H12	122.6	C2—N3—C8	103.9 (3)
C11—C12—H12	122.6	C2—N3—Cu1	113.0 (2)
C12—C13—C14	123.4 (3)	C8—N3—Cu1	143.2 (2)
C12—C13—H13	118.3	C10—N4—C11	107.2 (3)
C14—C13—H13	118.3	C10—N4—H4A	126.4
C15—C14—C13	120.5 (3)	C11—N4—H4A	126.4
C15—C14—H14	119.8	C10—N5—C16	107.5 (3)
C13—C14—H14	119.8	C10—N5—Cu1	110.1 (2)
C14—C15—C16	118.3 (3)	C16—N5—Cu1	142.4 (2)
C14—C15—H15	120.9	C18—N6—C19	108.4 (3)
C16—C15—H15	120.9	C18—N6—H6A	125.8
C11—C16—C15	119.9 (3)	C19—N6—H6A	125.8
C11—C16—N5	108.5 (3)	C18—N7—C24	106.1 (3)
C15—C16—N5	131.6 (3)	C18—N7—Cu1	112.8 (2)
C18—C17—N1	109.5 (3)	C24—N7—Cu1	141.1 (2)
C18—C17—H17A	109.8	O2—N8—C29	122.2 (3)
N1—C17—H17A	109.8	O2—N8—C25	118.9 (3)
C18—C17—H17B	109.8	C29—N8—C25	119.0 (3)
N1—C17—H17B	109.8	O4—N9—O3	124.7 (3)
H17A—C17—H17B	108.2	O4—N9—C27	120.0 (3)
N7—C18—N6	111.2 (3)	O3—N9—C27	115.3 (3)
N7—C18—C17	122.4 (3)	Cu1—O1—H1C	109.5
N6—C18—C17	126.2 (3)	Cu1—O1—H1E	109.5
C20—C19—N6	131.6 (3)	H1C—O1—H1E	109.8
C20—C19—C24	122.9 (3)	H1WD—O1W—H1WC	109.5
N6—C19—C24	105.5 (3)	H2WD—O2W—H2WC	109.5
C21—C20—C19	116.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···O21	0.85	2.44	3.230 (4)	156
O1—H1E···O2^i	0.82	2.17	2.807 (3)	135
O1W—H1WC···O1	0.85	2.34	2.733 (5)	108
N4—H4A···O2^ii	0.86	2.57	3.274 (4)	139
N4—H4A···O14^ii	0.86	2.48	3.159 (4)	136
N6—H6A···O24^iii	0.86	2.14	2.964 (4)	161
C1—H1A···O12^iv	0.97	2.49	3.353 (5)	147
C1—H1B···O24^v	0.97	2.54	3.469 (5)	160
C17—H17B···O11^ii	0.97	2.38	3.265 (4)	152
C26—H26···O4	0.93	2.38	2.704 (5)	100
C26—H26···O13^vi	0.93	2.47	3.284 (4)	146
C29—H29···O23^vii	0.93	2.55	3.183 (4)	126

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