Aqua­[tris(1H-benzimidazol-2-yl­methyl)­amine]copper(II) diperchlorate 4-picoline N-oxide monohydrate

In the title compound, [Cu(C₂₄H₂₁N₇)(H₂O)](ClO₄)₂·C₆H₇NO·H₂O, the copper ion is bonded to a tris(1H-benzimidazol-2-yl­methyl)­amine (ntb) and a water mol­ecule, resulting in it being five-coordinate with an N₄O ligand set. The coordination geometry of the copper ion may best be described as distorted trigonal bipyramidal, with C3 molecular symmetry.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in solvent or counterion
• R factor = 0.054
• wR factor = 0.171
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................       5.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              Cl O4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          6
              H4 O2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 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
   2 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 1996); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2004) and SHELXTL; software used to prepare material for publication: SHELXTL.

Aqua[tris(1H-benzimidazol-2-ylmethyl)amine]copper(II) diperchlorate 4-picoline N-oxide monohydrate

Crystal data

[Cu(C24H21N7)(H2O)](ClO4)2·C6H7NO·H2O	Z = 2
Mr = 815.08	F(000) = 838
Triclinic, P1	Dx = 1.485 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.6048 (13) Å	Cell parameters from 2688 reflections
b = 13.8916 (15) Å	θ = 2.3–23.1°
c = 14.3273 (16) Å	µ = 0.81 mm^−1
α = 62.430 (2)°	T = 293 K
β = 89.898 (2)°	Cuboid, blue-green
γ = 66.140 (2)°	0.3 × 0.2 × 0.2 mm
V = 1822.8 (4) Å^3

Data collection

Bruker SMART CCD diffractometer	6971 independent reflections
Radiation source: fine-focus sealed tube	4936 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −14→13
Tmin = 0.82, Tmax = 0.85	k = −17→11
9837 measured reflections	l = −17→12

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.171	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.1057P)^2 + 0.3685P] where P = (Fo^2 + 2Fc^2)/3
6971 reflections	(Δ/σ)max < 0.001
485 parameters	Δρmax = 0.31 e Å^−3
1 restraint	Δρmin = −0.33 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	0.50078 (4)	0.34966 (4)	0.34048 (4)	0.04824 (17)
C1	0.7636 (4)	0.2685 (3)	0.3031 (3)	0.0510 (9)
H1A	0.7781	0.2049	0.2865	0.061*
H1B	0.8463	0.2660	0.3192	0.061*
C2	0.6735 (4)	0.3903 (3)	0.2095 (3)	0.0495 (8)
C3	0.5965 (4)	0.5610 (4)	0.0552 (3)	0.0514 (9)
C4	0.5718 (4)	0.6631 (4)	−0.0423 (3)	0.0524 (9)
H4	0.6385	0.6738	−0.0749	0.063*
C5	0.4449 (4)	0.7489 (4)	−0.0898 (3)	0.0545 (9)
H5	0.4253	0.8184	−0.1565	0.065*
C6	0.3493 (4)	0.7350 (4)	−0.0427 (3)	0.0493 (8)
H6	0.2649	0.7963	−0.0769	0.059*
C7	0.3704 (4)	0.6328 (3)	0.0552 (3)	0.0495 (8)
H7	0.3021	0.6238	0.0857	0.059*
C8	0.4964 (4)	0.5453 (3)	0.1053 (3)	0.0492 (8)
C9	0.7385 (4)	0.2975 (4)	0.4601 (3)	0.0486 (8)
H9A	0.8219	0.2379	0.5100	0.058*
H9B	0.7437	0.3721	0.4123	0.058*
C10	0.6371 (4)	0.3211 (3)	0.5199 (3)	0.0487 (8)
C11	0.5289 (4)	0.3407 (3)	0.6404 (3)	0.0491 (8)
C12	0.4912 (4)	0.3410 (3)	0.7314 (3)	0.0485 (8)
H12	0.5489	0.3230	0.7889	0.058*
C13	0.3643 (4)	0.3692 (3)	0.7325 (3)	0.0506 (9)
H13	0.3357	0.3669	0.7938	0.061*
C14	0.2765 (4)	0.4011 (3)	0.6454 (3)	0.0517 (9)
H14	0.1900	0.4227	0.6478	0.062*
C15	0.3177 (4)	0.4009 (3)	0.5541 (3)	0.0481 (8)
H15	0.2592	0.4224	0.4953	0.058*
C16	0.4456 (4)	0.3685 (3)	0.5524 (3)	0.0508 (9)
C17	0.7363 (4)	0.1203 (3)	0.4671 (3)	0.0497 (9)
H17A	0.7289	0.1028	0.5401	0.060*
H17B	0.8245	0.0693	0.4695	0.060*
C18	0.6443 (4)	0.0969 (3)	0.4202 (3)	0.0484 (8)
C19	0.5604 (4)	0.0028 (3)	0.3768 (3)	0.0520 (9)
C20	0.5327 (4)	−0.0745 (4)	0.3580 (3)	0.0532 (9)
H20	0.5942	−0.1547	0.3838	0.064*
C21	0.4122 (4)	−0.0298 (4)	0.3005 (3)	0.0531 (9)
H21	0.3917	−0.0804	0.2858	0.064*
C22	0.3192 (4)	0.0894 (4)	0.2630 (3)	0.0504 (9)
H22	0.2375	0.1163	0.2246	0.060*
C23	0.3444 (4)	0.1683 (3)	0.2809 (3)	0.0489 (8)
H23	0.2821	0.2481	0.2558	0.059*
C24	0.4676 (4)	0.1232 (3)	0.3385 (3)	0.0480 (8)
N1	0.7024 (3)	0.2504 (3)	0.3965 (3)	0.0476 (7)
N2	0.7076 (3)	0.4596 (3)	0.1247 (3)	0.0485 (7)
H2A	0.7851	0.4435	0.1155	0.058*
N3	0.5506 (3)	0.4380 (3)	0.2032 (3)	0.0497 (7)
N4	0.6504 (3)	0.3132 (3)	0.6147 (3)	0.0488 (7)
H4A	0.7205	0.2947	0.6536	0.059*
N5	0.5154 (3)	0.3546 (3)	0.4786 (3)	0.0490 (7)
N6	0.6696 (3)	−0.0113 (3)	0.4293 (3)	0.0498 (7)
H6A	0.7415	−0.0772	0.4621	0.060*
N7	0.5253 (3)	0.1800 (3)	0.3674 (3)	0.0493 (7)
O1	0.3126 (3)	0.4458 (2)	0.2873 (2)	0.0487 (6)
H1C	0.279 (4)	0.513 (3)	0.280 (4)	0.058*
H1D	0.266 (4)	0.418 (4)	0.320 (3)	0.058*
C25	0.9607 (4)	0.1920 (4)	0.8957 (3)	0.0532 (9)
H25A	0.8965	0.1920	0.9346	0.064*
C26	1.0882 (4)	0.1155 (4)	0.9495 (3)	0.0543 (9)
H26A	1.1082	0.0629	1.0238	0.065*
C27	1.1840 (4)	0.1149 (4)	0.8981 (3)	0.0526 (9)
C28	1.1477 (4)	0.1899 (4)	0.7901 (3)	0.0533 (9)
H28A	1.2114	0.1925	0.7508	0.064*
C29	1.0202 (4)	0.2625 (4)	0.7358 (3)	0.0534 (9)
H29A	0.9981	0.3103	0.6607	0.064*
C30	1.3312 (4)	0.0401 (4)	0.9505 (3)	0.0528 (9)
H30A	1.3510	−0.0429	1.0015	0.079*
H30B	1.3548	0.0746	0.9871	0.079*
H30C	1.3788	0.0422	0.8953	0.079*
N8	0.9282 (3)	0.2639 (3)	0.7918 (3)	0.0507 (7)
O2	0.8054 (3)	0.3350 (2)	0.7388 (2)	0.0507 (6)
Cl1	0.93211 (9)	−0.33414 (9)	0.58944 (8)	0.0520 (2)
O11	0.9749 (3)	−0.3961 (3)	0.5335 (2)	0.0565 (7)
O12	0.7999 (3)	−0.2967 (2)	0.5804 (2)	0.0545 (6)
O13	0.9352 (3)	−0.2232 (2)	0.5465 (2)	0.0565 (7)
O14	0.9982 (3)	−0.4192 (2)	0.6935 (2)	0.0558 (7)
Cl2	1.00301 (9)	0.01759 (8)	0.25849 (8)	0.0516 (2)
O21	0.9869 (3)	0.1253 (2)	0.1735 (2)	0.0568 (7)
O22	0.8882 (3)	0.0115 (2)	0.2578 (2)	0.0558 (7)
O23	1.1131 (3)	−0.0801 (2)	0.2731 (2)	0.0572 (7)
O24	1.0190 (3)	0.0226 (3)	0.3470 (2)	0.0576 (7)
O1W	0.9644 (5)	0.3613 (5)	0.0978 (4)	0.0526 (12)	0.50
H1WB	0.9707	0.2906	0.1206	0.063*	0.50
H1WA	0.9527	0.3981	0.0293	0.063*	0.50
O2W	0.9988 (6)	−0.4987 (5)	0.8495 (5)	0.0586 (14)	0.50
H2WC	0.9400	−0.5168	0.8761	0.070*	0.50
H2WD	1.0716	−0.5620	0.8782	0.070*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0465 (3)	0.0480 (3)	0.0494 (3)	−0.0213 (2)	0.0101 (2)	−0.0241 (2)
C1	0.048 (2)	0.049 (2)	0.058 (2)	−0.0229 (16)	0.0080 (17)	−0.0272 (19)
C2	0.053 (2)	0.0471 (19)	0.046 (2)	−0.0234 (17)	0.0112 (17)	−0.0210 (17)
C3	0.056 (2)	0.052 (2)	0.052 (2)	−0.0270 (18)	0.0150 (18)	−0.0291 (19)
C4	0.052 (2)	0.054 (2)	0.050 (2)	−0.0250 (17)	0.0110 (17)	−0.0243 (19)
C5	0.058 (2)	0.047 (2)	0.051 (2)	−0.0213 (17)	0.0116 (18)	−0.0203 (18)
C6	0.049 (2)	0.052 (2)	0.046 (2)	−0.0213 (17)	0.0076 (16)	−0.0251 (18)
C7	0.052 (2)	0.049 (2)	0.047 (2)	−0.0225 (17)	0.0092 (16)	−0.0246 (17)
C8	0.048 (2)	0.051 (2)	0.051 (2)	−0.0234 (16)	0.0119 (16)	−0.0261 (18)
C9	0.0464 (19)	0.0476 (19)	0.050 (2)	−0.0202 (16)	0.0109 (16)	−0.0241 (17)
C10	0.048 (2)	0.050 (2)	0.050 (2)	−0.0241 (16)	0.0107 (16)	−0.0245 (18)
C11	0.051 (2)	0.048 (2)	0.048 (2)	−0.0205 (17)	0.0107 (17)	−0.0262 (18)
C12	0.052 (2)	0.050 (2)	0.046 (2)	−0.0236 (17)	0.0093 (16)	−0.0262 (18)
C13	0.052 (2)	0.051 (2)	0.054 (2)	−0.0242 (17)	0.0115 (17)	−0.0296 (19)
C14	0.051 (2)	0.046 (2)	0.055 (2)	−0.0190 (17)	0.0136 (18)	−0.0251 (18)
C15	0.050 (2)	0.0456 (19)	0.047 (2)	−0.0215 (16)	0.0102 (16)	−0.0229 (17)
C16	0.054 (2)	0.0452 (19)	0.050 (2)	−0.0213 (17)	0.0107 (18)	−0.0227 (17)
C17	0.048 (2)	0.0444 (19)	0.051 (2)	−0.0190 (16)	0.0121 (17)	−0.0219 (17)
C18	0.048 (2)	0.0434 (19)	0.049 (2)	−0.0189 (16)	0.0098 (16)	−0.0209 (17)
C19	0.056 (2)	0.048 (2)	0.053 (2)	−0.0232 (17)	0.0140 (18)	−0.0270 (19)
C20	0.058 (2)	0.047 (2)	0.053 (2)	−0.0249 (18)	0.0145 (18)	−0.0234 (19)
C21	0.055 (2)	0.052 (2)	0.054 (2)	−0.0239 (18)	0.0141 (18)	−0.0288 (19)
C22	0.049 (2)	0.055 (2)	0.051 (2)	−0.0258 (17)	0.0141 (17)	−0.0282 (18)
C23	0.054 (2)	0.0454 (19)	0.050 (2)	−0.0228 (16)	0.0132 (17)	−0.0252 (17)
C24	0.048 (2)	0.0465 (19)	0.051 (2)	−0.0206 (16)	0.0141 (17)	−0.0262 (18)
N1	0.0454 (16)	0.0447 (16)	0.0486 (17)	−0.0189 (13)	0.0103 (13)	−0.0221 (14)
N2	0.0463 (17)	0.0521 (17)	0.0520 (18)	−0.0233 (14)	0.0127 (14)	−0.0292 (15)
N3	0.0520 (18)	0.0479 (17)	0.0489 (17)	−0.0240 (14)	0.0127 (14)	−0.0233 (15)
N4	0.0468 (17)	0.0491 (17)	0.0542 (19)	−0.0223 (14)	0.0090 (14)	−0.0284 (16)
N5	0.0484 (17)	0.0518 (17)	0.0484 (17)	−0.0232 (14)	0.0097 (14)	−0.0260 (15)
N6	0.0511 (18)	0.0463 (16)	0.0544 (19)	−0.0229 (14)	0.0119 (15)	−0.0265 (15)
N7	0.0496 (17)	0.0492 (17)	0.0492 (17)	−0.0231 (14)	0.0101 (14)	−0.0244 (15)
O1	0.0497 (15)	0.0485 (14)	0.0486 (15)	−0.0223 (12)	0.0124 (12)	−0.0251 (13)
C25	0.053 (2)	0.056 (2)	0.052 (2)	−0.0234 (18)	0.0105 (18)	−0.028 (2)
C26	0.053 (2)	0.054 (2)	0.049 (2)	−0.0198 (18)	0.0103 (17)	−0.0246 (19)
C27	0.048 (2)	0.052 (2)	0.053 (2)	−0.0218 (17)	0.0089 (17)	−0.0240 (19)
C28	0.054 (2)	0.051 (2)	0.059 (2)	−0.0260 (18)	0.0152 (18)	−0.029 (2)
C29	0.055 (2)	0.056 (2)	0.051 (2)	−0.0273 (18)	0.0137 (18)	−0.0257 (19)
C30	0.052 (2)	0.052 (2)	0.051 (2)	−0.0220 (17)	0.0105 (17)	−0.0244 (18)
N8	0.0478 (18)	0.0479 (17)	0.0490 (18)	−0.0170 (14)	0.0080 (15)	−0.0232 (15)
O2	0.0510 (15)	0.0479 (14)	0.0501 (14)	−0.0211 (12)	0.0059 (12)	−0.0236 (12)
Cl1	0.0501 (5)	0.0527 (5)	0.0541 (5)	−0.0238 (4)	0.0124 (4)	−0.0273 (5)
O11	0.0577 (16)	0.0565 (16)	0.0567 (16)	−0.0264 (13)	0.0144 (13)	−0.0293 (14)
O12	0.0516 (15)	0.0542 (15)	0.0548 (16)	−0.0236 (12)	0.0118 (12)	−0.0259 (13)
O13	0.0574 (16)	0.0521 (15)	0.0574 (17)	−0.0228 (13)	0.0135 (13)	−0.0277 (14)
O14	0.0541 (15)	0.0539 (15)	0.0532 (16)	−0.0217 (13)	0.0099 (13)	−0.0250 (14)
Cl2	0.0502 (5)	0.0504 (5)	0.0528 (5)	−0.0208 (4)	0.0107 (4)	−0.0267 (4)
O21	0.0580 (16)	0.0551 (15)	0.0555 (16)	−0.0271 (13)	0.0148 (13)	−0.0254 (14)
O22	0.0553 (16)	0.0536 (15)	0.0559 (16)	−0.0248 (13)	0.0109 (13)	−0.0257 (13)
O23	0.0571 (16)	0.0496 (15)	0.0587 (17)	−0.0203 (13)	0.0132 (13)	−0.0263 (14)
O24	0.0578 (16)	0.0576 (16)	0.0533 (16)	−0.0241 (13)	0.0135 (13)	−0.0267 (14)
O1W	0.056 (3)	0.050 (3)	0.049 (3)	−0.025 (2)	0.015 (2)	−0.023 (3)
O2W	0.059 (3)	0.055 (3)	0.057 (3)	−0.023 (3)	0.017 (3)	−0.028 (3)

Geometric parameters (Å, º)

Cu1—O1	1.959 (3)	C18—N6	1.350 (5)
Cu1—N3	2.011 (3)	C19—C20	1.369 (5)
Cu1—N5	2.021 (3)	C19—N6	1.370 (5)
Cu1—N1	2.096 (3)	C19—C24	1.397 (5)
Cu1—N7	2.098 (3)	C20—C21	1.360 (6)
C1—N1	1.480 (5)	C20—H20	0.9300
C1—C2	1.493 (5)	C21—C22	1.389 (5)
C1—H1A	0.9700	C21—H21	0.9300
C1—H1B	0.9700	C22—C23	1.370 (5)
C2—N3	1.289 (5)	C22—H22	0.9300
C2—N2	1.335 (5)	C23—C24	1.384 (5)
C3—N2	1.370 (5)	C23—H23	0.9300
C3—C4	1.373 (5)	C24—N7	1.405 (5)
C3—C8	1.404 (5)	N2—H2A	0.8600
C4—C5	1.373 (6)	N4—H4A	0.8600
C4—H4	0.9300	N6—H6A	0.8600
C5—C6	1.333 (6)	O1—H1C	0.81 (3)
C5—H5	0.9300	O1—H1D	0.81 (3)
C6—C7	1.385 (5)	C25—N8	1.295 (5)
C6—H6	0.9300	C25—C26	1.373 (6)
C7—C8	1.374 (5)	C25—H25A	0.9300
C7—H7	0.9300	C26—C27	1.332 (6)
C8—N3	1.376 (5)	C26—H26A	0.9300
C9—C10	1.473 (5)	C27—C28	1.347 (6)
C9—N1	1.486 (5)	C27—C30	1.552 (5)
C9—H9A	0.9700	C28—C29	1.372 (6)
C9—H9B	0.9700	C28—H28A	0.9300
C10—N4	1.314 (5)	C29—N8	1.334 (5)
C10—N5	1.334 (5)	C29—H29A	0.9300
C11—C12	1.376 (5)	C30—H30A	0.9600
C11—C16	1.388 (5)	C30—H30B	0.9600
C11—N4	1.400 (5)	C30—H30C	0.9600
C12—C13	1.365 (5)	N8—O2	1.324 (4)
C12—H12	0.9300	Cl1—O14	1.360 (3)
C13—C14	1.385 (6)	Cl1—O11	1.386 (3)
C13—H13	0.9300	Cl1—O13	1.386 (3)
C14—C15	1.392 (6)	Cl1—O12	1.391 (3)
C14—H14	0.9300	Cl2—O24	1.320 (3)
C15—C16	1.370 (5)	Cl2—O21	1.358 (3)
C15—H15	0.9300	Cl2—O23	1.361 (3)
C16—N5	1.368 (5)	Cl2—O22	1.370 (3)
C17—N1	1.476 (5)	O1W—H1WB	0.8498
C17—C18	1.478 (5)	O1W—H1WA	0.8500
C17—H17A	0.9700	O2W—H2WC	0.8502
C17—H17B	0.9700	O2W—H2WD	0.8500
C18—N7	1.311 (5)
O1—Cu1—N3	97.85 (12)	C19—C20—H20	121.1
O1—Cu1—N5	98.21 (12)	C20—C21—C22	121.6 (4)
N3—Cu1—N5	128.80 (13)	C20—C21—H21	119.2
O1—Cu1—N1	178.71 (11)	C22—C21—H21	119.2
N3—Cu1—N1	81.49 (13)	C23—C22—C21	121.8 (4)
N5—Cu1—N1	81.40 (13)	C23—C22—H22	119.1
O1—Cu1—N7	100.65 (12)	C21—C22—H22	119.1
N3—Cu1—N7	111.30 (13)	C22—C23—C24	116.6 (4)
N5—Cu1—N7	112.87 (13)	C22—C23—H23	121.7
N1—Cu1—N7	80.62 (12)	C24—C23—H23	121.7
N1—C1—C2	107.2 (3)	C23—C24—C19	121.4 (4)
N1—C1—H1A	110.3	C23—C24—N7	130.9 (3)
C2—C1—H1A	110.3	C19—C24—N7	107.8 (3)
N1—C1—H1B	110.3	C17—N1—C1	110.7 (3)
C2—C1—H1B	110.3	C17—N1—C9	110.1 (3)
H1A—C1—H1B	108.5	C1—N1—C9	112.1 (3)
N3—C2—N2	113.2 (3)	C17—N1—Cu1	108.5 (2)
N3—C2—C1	121.2 (3)	C1—N1—Cu1	109.3 (2)
N2—C2—C1	125.6 (3)	C9—N1—Cu1	106.0 (2)
N2—C3—C4	133.5 (4)	C2—N2—C3	107.3 (3)
N2—C3—C8	105.0 (3)	C2—N2—H2A	126.3
C4—C3—C8	121.5 (4)	C3—N2—H2A	126.3
C3—C4—C5	117.4 (4)	C2—N3—C8	106.1 (3)
C3—C4—H4	121.3	C2—N3—Cu1	113.6 (3)
C5—C4—H4	121.3	C8—N3—Cu1	139.6 (3)
C6—C5—C4	121.6 (4)	C10—N4—C11	107.2 (3)
C6—C5—H5	119.2	C10—N4—H4A	126.4
C4—C5—H5	119.2	C11—N4—H4A	126.4
C5—C6—C7	122.7 (4)	C10—N5—C16	106.5 (3)
C5—C6—H6	118.7	C10—N5—Cu1	111.4 (3)
C7—C6—H6	118.7	C16—N5—Cu1	141.6 (3)
C8—C7—C6	117.3 (4)	C18—N6—C19	107.7 (3)
C8—C7—H7	121.3	C18—N6—H6A	126.1
C6—C7—H7	121.3	C19—N6—H6A	126.1
C7—C8—N3	132.1 (4)	C18—N7—C24	106.1 (3)
C7—C8—C3	119.5 (4)	C18—N7—Cu1	109.7 (2)
N3—C8—C3	108.3 (3)	C24—N7—Cu1	143.4 (3)
C10—C9—N1	107.1 (3)	Cu1—O1—H1C	118 (3)
C10—C9—H9A	110.3	Cu1—O1—H1D	119 (3)
N1—C9—H9A	110.3	H1C—O1—H1D	100 (5)
C10—C9—H9B	110.3	N8—C25—C26	121.3 (4)
N1—C9—H9B	110.3	N8—C25—H25A	119.4
H9A—C9—H9B	108.5	C26—C25—H25A	119.4
N4—C10—N5	112.2 (3)	C27—C26—C25	121.7 (4)
N4—C10—C9	127.5 (3)	C27—C26—H26A	119.2
N5—C10—C9	120.3 (4)	C25—C26—H26A	119.2
C12—C11—C16	123.7 (4)	C26—C27—C28	115.9 (4)
C12—C11—N4	130.7 (4)	C26—C27—C30	126.6 (4)
C16—C11—N4	105.6 (3)	C28—C27—C30	117.5 (4)
C13—C12—C11	116.2 (4)	C27—C28—C29	122.4 (4)
C13—C12—H12	121.9	C27—C28—H28A	118.8
C11—C12—H12	121.9	C29—C28—H28A	118.8
C12—C13—C14	122.3 (4)	N8—C29—C28	119.3 (4)
C12—C13—H13	118.9	N8—C29—H29A	120.4
C14—C13—H13	118.9	C28—C29—H29A	120.4
C13—C14—C15	120.1 (4)	C27—C30—H30A	109.5
C13—C14—H14	120.0	C27—C30—H30B	109.5
C15—C14—H14	120.0	H30A—C30—H30B	109.5
C16—C15—C14	118.9 (4)	C27—C30—H30C	109.5
C16—C15—H15	120.5	H30A—C30—H30C	109.5
C14—C15—H15	120.5	H30B—C30—H30C	109.5
N5—C16—C15	132.8 (4)	C25—N8—O2	121.7 (3)
N5—C16—C11	108.4 (3)	C25—N8—C29	119.4 (3)
C15—C16—C11	118.8 (4)	O2—N8—C29	118.8 (3)
N1—C17—C18	106.6 (3)	O14—Cl1—O11	104.05 (18)
N1—C17—H17A	110.4	O14—Cl1—O13	116.85 (18)
C18—C17—H17A	110.4	O11—Cl1—O13	116.09 (18)
N1—C17—H17B	110.4	O14—Cl1—O12	110.56 (17)
C18—C17—H17B	110.4	O11—Cl1—O12	108.32 (18)
H17A—C17—H17B	108.6	O13—Cl1—O12	100.81 (17)
N7—C18—N6	112.2 (3)	O24—Cl2—O21	107.14 (18)
N7—C18—C17	122.8 (3)	O24—Cl2—O23	104.35 (19)
N6—C18—C17	125.0 (3)	O21—Cl2—O23	113.65 (18)
C20—C19—N6	132.8 (4)	O24—Cl2—O22	101.63 (19)
C20—C19—C24	121.0 (4)	O21—Cl2—O22	109.53 (18)
N6—C19—C24	106.2 (3)	O23—Cl2—O22	119.01 (18)
C21—C20—C19	117.7 (4)	H1WB—O1W—H1WA	109.5
C21—C20—H20	121.1	H2WC—O2W—H2WD	109.8

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1W	0.86	2.01	2.844 (6)	163
N4—H4A···O2	0.86	1.96	2.728 (4)	147
N4—H4A···O23^i	0.86	2.48	2.935 (4)	114
N6—H6A···O13	0.86	2.16	3.015 (4)	170
N6—H6A···O12	0.86	2.49	3.148 (4)	134
O1—H1C···O2^ii	0.81 (3)	1.81 (3)	2.620 (4)	177 (5)
O1—H1D···O12^iii	0.81 (3)	2.07 (3)	2.852 (4)	162 (4)
O1W—H1WB···O21	0.85	1.98	2.830 (6)	180
O1W—H1WA···O2W^iv	0.85	2.48	3.288 (8)	158
C14—H14···O11^v	0.93	2.52	3.259 (5)	136

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