A second polymorph of {tris­[2-(5-methylimidazol-4-yl­methyl­imino)eth­yl]amino}copper(II) diperchlorate

The crystal structure of the title compound, [Cu(C₂₁H₃₀N₁₀)](ClO₄)₂, has recently been reported to crystallize in P2₁/c [Brewer, Brewer, Butcher & Carpenter (2006). Inorg. Chim. Acta, 359, 1263–1268]. The structure of a second polymorph crystallizes in P2₁ with different cell dimensions. In the crystal structure, the Cu^II complex cations are bridged by perchlorate anions through N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.014 Å
• R factor = 0.082
• wR factor = 0.243
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.30
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl2
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         14
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          3

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.00
           From the CIF: _reflns_number_total               5771
           Count of symmetry unique reflns         3319
           Completeness (_total/calc)            173.88%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2452
           Fraction of Friedel pairs measured     0.739
           Are heavy atom types Z>Si present        yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

{tris[2-(5-methylimidazol-4-ylmethylimino)ethyl]amino}copper(II) bis(perchlorate)

Crystal data

[Cu(C21H30N10)](ClO4)2	F(000) = 706
Mr = 684.99	Dx = 1.560 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3045 reflections
a = 10.7278 (6) Å	θ = 1.0–27.5°
b = 13.8859 (6) Å	µ = 1.00 mm^−1
c = 11.1108 (7) Å	T = 293 K
β = 118.220 (2)°	Thin plate, green
V = 1458.39 (14) Å^3	0.23 × 0.11 × 0.04 mm
Z = 2

Data collection

Nonius KappaCCD diffractometer	5771 independent reflections
Radiation source: fine-focus sealed tube	4982 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
φ and ω scans	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (DENZO; Otwinowski & Minor, 1997)	h = −13→12
Tmin = 0.804, Tmax = 0.961	k = −15→17
5771 measured reflections	l = 0→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.082	H-atom parameters constrained
wR(F^2) = 0.244	w = 1/[σ^2(Fo^2) + (0.1344P)^2 + 6.0122P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
5771 reflections	Δρmax = 2.16 e Å^−3
382 parameters	Δρmin = −0.94 e Å^−3
1 restraint	Absolute structure: Flack (1983), 2461 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.06 (3)

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

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
Cu	0.35175 (10)	0.16513 (7)	0.16139 (10)	0.0348 (3)
Cl1	0.3518 (2)	0.75204 (17)	0.1958 (2)	0.0393 (5)
O1	0.2727 (8)	0.8092 (7)	0.0764 (7)	0.060 (2)
O2	0.5000 (8)	0.7789 (8)	0.2568 (8)	0.071 (3)
O3	0.3341 (10)	0.6544 (8)	0.1575 (9)	0.072 (2)
O4	0.2977 (8)	0.7666 (6)	0.2902 (7)	0.0501 (16)
Cl2	0.9861 (2)	0.31374 (16)	0.4828 (2)	0.0417 (5)
O5	0.9879 (11)	0.2126 (6)	0.4997 (10)	0.065 (2)
O6	0.8530 (10)	0.3421 (7)	0.3644 (10)	0.072 (2)
O7	1.1014 (11)	0.3401 (9)	0.4621 (11)	0.081 (3)
O8	0.9971 (10)	0.3561 (7)	0.6057 (9)	0.066 (2)
N1	0.3244 (7)	0.3992 (6)	0.1518 (7)	0.0348 (15)
N2	0.1311 (8)	0.2471 (5)	0.0551 (8)	0.0348 (15)
N3	0.2336 (7)	0.0902 (6)	−0.0143 (7)	0.0347 (15)
N4	0.1334 (9)	−0.0061 (6)	−0.1878 (8)	0.0452 (19)
NH4	0.1218	−0.0538	−0.2416	0.054*
N5	0.4279 (8)	0.2419 (6)	0.3413 (7)	0.0371 (16)
N6	0.2884 (9)	0.0781 (6)	0.2682 (8)	0.0415 (17)
N7	0.2104 (8)	−0.0162 (5)	0.3739 (8)	0.0392 (17)
NH7	0.1694	−0.0646	0.3886	0.047*
N8	0.4532 (7)	0.2428 (5)	0.0779 (7)	0.0331 (14)
N9	0.5639 (9)	0.0705 (7)	0.2250 (9)	0.0468 (19)
N10	0.7760 (9)	0.0064 (6)	0.2869 (9)	0.049 (2)
NH10	0.8462	−0.0328	0.3238	0.058*
C1	0.1762 (9)	0.4209 (6)	0.0785 (10)	0.039 (2)
H1A	0.1483	0.4306	−0.0173	0.047*
H1B	0.1572	0.4799	0.1138	0.047*
C2	0.0905 (10)	0.3384 (6)	0.0938 (10)	0.0389 (19)
H2A	0.1079	0.3349	0.1876	0.047*
H2B	−0.0096	0.3500	0.0358	0.047*
C3	0.0493 (10)	0.2091 (7)	−0.0594 (10)	0.042 (2)
H3	−0.0394	0.2350	−0.1163	0.050*
C4	0.0999 (10)	0.1230 (6)	−0.0981 (9)	0.0358 (18)
C5	0.2504 (12)	0.0109 (8)	−0.0703 (11)	0.047 (2)
H5	0.3311	−0.0273	−0.0335	0.057*
C6	0.0337 (11)	0.0648 (7)	−0.2100 (10)	0.044 (2)
C7	−0.1038 (12)	0.0664 (8)	−0.3311 (10)	0.048 (2)
H7A	−0.1555	0.1221	−0.3286	0.073*
H7B	−0.1555	0.0093	−0.3336	0.073*
H7C	−0.0913	0.0689	−0.4111	0.073*
C8	0.3981 (11)	0.4161 (6)	0.2982 (10)	0.042 (2)
H8A	0.3296	0.4215	0.3316	0.050*
H8B	0.4493	0.4765	0.3166	0.050*
C9	0.5028 (10)	0.3341 (7)	0.3750 (10)	0.0388 (19)
H9A	0.5775	0.3328	0.3493	0.047*
H9B	0.5456	0.3452	0.4727	0.047*
C10	0.3916 (9)	0.2074 (7)	0.4277 (10)	0.0391 (19)
H10	0.4124	0.2390	0.5089	0.047*
C11	0.3167 (9)	0.1168 (7)	0.3915 (9)	0.0357 (18)
C12	0.2249 (11)	−0.0043 (7)	0.2598 (11)	0.045 (2)
H12	0.1947	−0.0476	0.1874	0.054*
C13	0.2671 (10)	0.0558 (7)	0.4587 (10)	0.042 (2)
C14	0.2707 (11)	0.0662 (9)	0.5940 (10)	0.050 (2)
H14A	0.1890	0.1015	0.5829	0.075*
H14B	0.3548	0.1002	0.6556	0.075*
H14C	0.2705	0.0035	0.6304	0.075*
C15	0.4061 (10)	0.4159 (6)	0.0797 (9)	0.0377 (19)
H15A	0.5042	0.4280	0.1452	0.045*
H15B	0.3697	0.4722	0.0216	0.045*
C16	0.3967 (9)	0.3279 (6)	−0.0075 (9)	0.0361 (18)
H16A	0.2988	0.3166	−0.0742	0.043*
H16B	0.4497	0.3401	−0.0565	0.043*
C17	0.5776 (9)	0.2120 (6)	0.1023 (9)	0.0345 (17)
H17	0.6270	0.2464	0.0666	0.041*
C18	0.6407 (10)	0.1292 (7)	0.1802 (9)	0.0383 (19)
C19	0.6519 (11)	−0.0046 (7)	0.2894 (11)	0.047 (2)
H19	0.6299	−0.0562	0.3295	0.057*
C20	0.7748 (9)	0.0885 (7)	0.2175 (9)	0.0371 (18)
C21	0.8930 (11)	0.1212 (9)	0.1942 (11)	0.050 (2)
H21A	0.9802	0.1169	0.2780	0.075*
H21B	0.8772	0.1868	0.1631	0.075*
H21C	0.8983	0.0812	0.1263	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu	0.0387 (5)	0.0269 (5)	0.0374 (5)	−0.0012 (4)	0.0169 (4)	0.0011 (5)
Cl1	0.0420 (11)	0.0331 (12)	0.0406 (10)	0.0007 (8)	0.0176 (9)	0.0029 (9)
O1	0.060 (4)	0.082 (6)	0.040 (3)	0.018 (4)	0.027 (3)	0.008 (4)
O2	0.037 (4)	0.114 (8)	0.053 (4)	−0.010 (4)	0.014 (3)	0.016 (5)
O3	0.098 (6)	0.040 (5)	0.082 (5)	0.013 (5)	0.045 (5)	0.001 (4)
O4	0.055 (4)	0.048 (4)	0.047 (3)	−0.006 (3)	0.025 (3)	0.000 (3)
Cl2	0.0505 (12)	0.0200 (10)	0.0524 (12)	0.0009 (8)	0.0225 (10)	0.0008 (9)
O5	0.087 (6)	0.023 (4)	0.080 (6)	0.000 (3)	0.035 (5)	−0.004 (3)
O6	0.065 (5)	0.064 (6)	0.073 (5)	0.006 (4)	0.020 (4)	0.021 (5)
O7	0.091 (7)	0.086 (7)	0.094 (7)	−0.015 (6)	0.065 (6)	−0.003 (6)
O8	0.077 (6)	0.057 (6)	0.074 (5)	0.002 (4)	0.043 (5)	−0.013 (4)
N1	0.034 (4)	0.023 (4)	0.040 (4)	0.004 (3)	0.012 (3)	0.005 (3)
N2	0.040 (4)	0.014 (3)	0.050 (4)	−0.002 (3)	0.022 (3)	−0.006 (3)
N3	0.034 (4)	0.030 (4)	0.038 (4)	0.002 (3)	0.015 (3)	0.000 (3)
N4	0.062 (5)	0.036 (5)	0.046 (4)	−0.008 (4)	0.033 (4)	−0.006 (3)
N5	0.040 (4)	0.027 (4)	0.038 (4)	0.001 (3)	0.013 (3)	0.006 (3)
N6	0.042 (4)	0.036 (5)	0.046 (4)	0.000 (3)	0.020 (3)	0.003 (3)
N7	0.039 (4)	0.020 (4)	0.052 (4)	−0.008 (3)	0.015 (3)	0.001 (3)
N8	0.036 (3)	0.021 (4)	0.042 (4)	−0.005 (3)	0.019 (3)	−0.005 (3)
N9	0.051 (5)	0.044 (5)	0.045 (4)	−0.004 (4)	0.023 (4)	0.000 (4)
N10	0.049 (5)	0.031 (5)	0.049 (4)	0.010 (4)	0.009 (4)	−0.001 (4)
C1	0.041 (5)	0.020 (4)	0.051 (5)	0.002 (3)	0.017 (4)	−0.004 (4)
C2	0.041 (5)	0.014 (4)	0.057 (5)	0.006 (3)	0.020 (4)	0.001 (4)
C3	0.044 (5)	0.036 (5)	0.047 (5)	−0.005 (4)	0.023 (4)	−0.002 (4)
C4	0.047 (5)	0.018 (4)	0.044 (5)	−0.002 (3)	0.023 (4)	0.001 (3)
C5	0.056 (6)	0.041 (6)	0.053 (5)	−0.003 (4)	0.032 (5)	−0.002 (4)
C6	0.060 (6)	0.031 (5)	0.052 (5)	−0.013 (4)	0.035 (5)	−0.002 (4)
C7	0.060 (6)	0.038 (6)	0.037 (5)	−0.018 (5)	0.015 (4)	−0.011 (4)
C8	0.056 (6)	0.014 (4)	0.052 (5)	−0.007 (4)	0.022 (4)	−0.006 (4)
C9	0.043 (5)	0.030 (5)	0.044 (5)	−0.007 (4)	0.021 (4)	−0.001 (4)
C10	0.035 (4)	0.040 (5)	0.044 (5)	0.005 (4)	0.020 (4)	0.002 (4)
C11	0.034 (4)	0.030 (5)	0.041 (4)	0.010 (3)	0.016 (4)	0.012 (4)
C12	0.060 (6)	0.020 (5)	0.063 (6)	−0.003 (4)	0.037 (5)	0.001 (4)
C13	0.041 (5)	0.040 (5)	0.050 (5)	0.011 (4)	0.024 (4)	0.008 (4)
C14	0.049 (6)	0.057 (7)	0.046 (5)	0.010 (5)	0.025 (5)	0.015 (5)
C15	0.044 (5)	0.022 (4)	0.044 (4)	0.014 (3)	0.018 (4)	0.011 (4)
C16	0.036 (4)	0.021 (4)	0.046 (5)	0.004 (3)	0.015 (4)	0.002 (3)
C17	0.040 (4)	0.026 (4)	0.039 (4)	−0.002 (3)	0.020 (4)	0.000 (3)
C18	0.040 (5)	0.033 (5)	0.041 (4)	0.001 (3)	0.018 (4)	−0.001 (3)
C19	0.062 (6)	0.021 (5)	0.054 (5)	−0.001 (4)	0.024 (5)	0.000 (4)
C20	0.041 (5)	0.025 (5)	0.038 (4)	0.006 (3)	0.014 (4)	−0.005 (3)
C21	0.043 (5)	0.052 (6)	0.055 (6)	0.006 (4)	0.023 (4)	−0.003 (5)

Geometric parameters (Å, º)

Cu—N2	2.377 (7)	C1—H1A	0.9700
Cu—N3	2.040 (7)	C1—H1B	0.9700
Cu—N5	2.062 (8)	C2—H2A	0.9700
Cu—N6	2.022 (8)	C2—H2B	0.9700
Cu—N8	2.041 (7)	C3—C4	1.459 (13)
Cu—N9	2.426 (9)	C3—H3	0.9300
Cl1—O3	1.406 (12)	C4—C6	1.368 (13)
Cl1—O1	1.430 (8)	C5—H5	0.9300
Cl1—O4	1.433 (7)	C6—C7	1.452 (15)
Cl1—O2	1.451 (8)	C7—H7A	0.9600
Cl2—O7	1.409 (9)	C7—H7B	0.9600
Cl2—O5	1.416 (9)	C7—H7C	0.9600
Cl2—O8	1.440 (9)	C8—C9	1.542 (13)
Cl2—O6	1.465 (9)	C8—H8A	0.9700
N1—C1	1.434 (11)	C8—H8B	0.9700
N1—C8	1.452 (12)	C9—H9A	0.9700
N1—C15	1.459 (12)	C9—H9B	0.9700
N2—C3	1.269 (12)	C10—C11	1.444 (13)
N2—C2	1.469 (10)	C10—H10	0.9300
N3—C5	1.318 (13)	C11—C13	1.390 (13)
N3—C4	1.368 (12)	C12—H12	0.9300
N4—C5	1.337 (14)	C13—C14	1.493 (14)
N4—C6	1.388 (14)	C14—H14A	0.9600
N4—NH4	0.8600	C14—H14B	0.9600
N5—C10	1.287 (12)	C14—H14C	0.9600
N5—C9	1.463 (12)	C15—C16	1.534 (13)
N6—C12	1.313 (13)	C15—H15A	0.9700
N6—C11	1.366 (12)	C15—H15B	0.9700
N7—C13	1.309 (13)	C16—H16A	0.9700
N7—C12	1.359 (12)	C16—H16B	0.9700
N7—NH7	0.8600	C17—C18	1.406 (13)
N8—C17	1.302 (11)	C17—H17	0.9300
N8—C16	1.455 (11)	C18—C20	1.413 (12)
N9—C19	1.361 (14)	C19—H19	0.9300
N9—C18	1.407 (13)	C20—C21	1.481 (14)
N10—C19	1.353 (15)	C21—H21A	0.9600
N10—C20	1.373 (14)	C21—H21B	0.9600
N10—NH10	0.8600	C21—H21C	0.9600
C1—C2	1.528 (13)
N2—Cu—N3	75.3 (3)	C6—C4—C3	130.3 (9)
N2—Cu—N5	94.5 (3)	N3—C5—N4	109.6 (9)
N2—Cu—N6	92.6 (3)	N3—C5—H5	125.2
N2—Cu—N8	98.1 (3)	N4—C5—H5	125.2
N2—Cu—N9	168.8 (3)	C4—C6—N4	103.5 (9)
N3—Cu—N5	166.7 (3)	C4—C6—C7	134.1 (10)
N3—Cu—N6	91.6 (3)	N4—C6—C7	122.4 (9)
N3—Cu—N8	93.3 (3)	C6—C7—H7A	109.5
N3—Cu—N9	94.3 (3)	C6—C7—H7B	109.5
N5—Cu—N6	80.2 (3)	H7A—C7—H7B	109.5
N5—Cu—N8	96.6 (3)	C6—C7—H7C	109.5
N5—Cu—N9	96.3 (3)	H7A—C7—H7C	109.5
N6—Cu—N8	169.0 (3)	H7B—C7—H7C	109.5
N6—Cu—N9	92.0 (3)	N1—C8—C9	111.7 (8)
N8—Cu—N9	77.9 (3)	N1—C8—H8A	109.3
O3—Cl1—O1	108.6 (6)	C9—C8—H8A	109.3
O3—Cl1—O4	108.3 (5)	N1—C8—H8B	109.3
O1—Cl1—O4	109.4 (4)	C9—C8—H8B	109.3
O3—Cl1—O2	110.6 (6)	H8A—C8—H8B	107.9
O1—Cl1—O2	109.2 (5)	N5—C9—C8	109.6 (7)
O4—Cl1—O2	110.8 (5)	N5—C9—H9A	109.7
O7—Cl2—O5	108.7 (7)	C8—C9—H9A	109.7
O7—Cl2—O8	111.4 (6)	N5—C9—H9B	109.7
O5—Cl2—O8	106.8 (6)	C8—C9—H9B	109.7
O7—Cl2—O6	110.0 (6)	H9A—C9—H9B	108.2
O5—Cl2—O6	109.4 (6)	N5—C10—C11	116.2 (9)
O8—Cl2—O6	110.5 (6)	N5—C10—H10	121.9
C1—N1—C8	118.2 (8)	C11—C10—H10	121.9
C1—N1—C15	116.6 (7)	N6—C11—C13	109.8 (9)
C8—N1—C15	116.0 (7)	N6—C11—C10	116.9 (8)
C3—N2—C2	119.5 (8)	C13—C11—C10	133.2 (9)
C3—N2—Cu	110.7 (6)	N6—C12—N7	108.9 (9)
C2—N2—Cu	129.1 (6)	N6—C12—H12	125.6
C5—N3—C4	106.9 (8)	N7—C12—H12	125.6
C5—N3—Cu	135.7 (7)	N7—C13—C11	104.2 (9)
C4—N3—Cu	117.3 (6)	N7—C13—C14	125.4 (9)
C5—N4—C6	109.6 (8)	C11—C13—C14	130.4 (10)
C5—N4—NH4	125.2	C13—C14—H14A	109.5
C6—N4—NH4	125.2	C13—C14—H14B	109.5
C10—N5—C9	117.2 (8)	H14A—C14—H14B	109.5
C10—N5—Cu	114.2 (7)	C13—C14—H14C	109.5
C9—N5—Cu	128.2 (6)	H14A—C14—H14C	109.5
C12—N6—C11	106.0 (8)	H14B—C14—H14C	109.5
C12—N6—Cu	141.8 (7)	N1—C15—C16	110.1 (8)
C11—N6—Cu	112.2 (6)	N1—C15—H15A	109.6
C13—N7—C12	111.1 (8)	C16—C15—H15A	109.6
C13—N7—NH7	124.5	N1—C15—H15B	109.6
C12—N7—NH7	124.5	C16—C15—H15B	109.6
C17—N8—C16	118.2 (7)	H15A—C15—H15B	108.2
C17—N8—Cu	116.5 (6)	N8—C16—C15	110.6 (7)
C16—N8—Cu	125.3 (5)	N8—C16—H16A	109.5
C19—N9—C18	104.7 (8)	C15—C16—H16A	109.5
C19—N9—Cu	152.9 (7)	N8—C16—H16B	109.5
C18—N9—Cu	102.0 (6)	C15—C16—H16B	109.5
C19—N10—C20	111.0 (8)	H16A—C16—H16B	108.1
C19—N10—NH10	124.5	N8—C17—C18	123.0 (8)
C20—N10—NH10	124.5	N8—C17—H17	118.5
N1—C1—C2	110.0 (7)	C18—C17—H17	118.5
N1—C1—H1A	109.7	C17—C18—N9	120.0 (8)
C2—C1—H1A	109.7	C17—C18—C20	129.4 (9)
N1—C1—H1B	109.7	N9—C18—C20	110.5 (8)
C2—C1—H1B	109.7	N10—C19—N9	110.3 (9)
H1A—C1—H1B	108.2	N10—C19—H19	124.8
N2—C2—C1	109.8 (7)	N9—C19—H19	124.8
N2—C2—H2A	109.7	N10—C20—C18	103.6 (8)
C1—C2—H2A	109.7	N10—C20—C21	124.9 (9)
N2—C2—H2B	109.7	C18—C20—C21	131.5 (9)
C1—C2—H2B	109.7	C20—C21—H21A	109.5
H2A—C2—H2B	108.2	C20—C21—H21B	109.5
N2—C3—C4	117.3 (9)	H21A—C21—H21B	109.5
N2—C3—H3	121.3	C20—C21—H21C	109.5
C4—C3—H3	121.3	H21A—C21—H21C	109.5
N3—C4—C6	110.4 (8)	H21B—C21—H21C	109.5
N3—C4—C3	119.3 (8)
N6—Cu—N2—C3	−93.6 (7)	Cu—N2—C2—C1	64.9 (10)
N3—Cu—N2—C3	−2.6 (6)	N1—C1—C2—N2	−52.9 (10)
N8—Cu—N2—C3	88.7 (6)	C2—N2—C3—C4	174.8 (8)
N5—Cu—N2—C3	−173.9 (6)	Cu—N2—C3—C4	3.7 (10)
N9—Cu—N2—C3	20.5 (18)	C5—N3—C4—C6	−1.8 (10)
N6—Cu—N2—C2	96.5 (7)	Cu—N3—C4—C6	−179.1 (6)
N3—Cu—N2—C2	−172.6 (8)	C5—N3—C4—C3	178.0 (8)
N8—Cu—N2—C2	−81.2 (7)	Cu—N3—C4—C3	0.6 (10)
N5—Cu—N2—C2	16.1 (7)	N2—C3—C4—N3	−3.2 (12)
N9—Cu—N2—C2	−149.5 (13)	N2—C3—C4—C6	176.4 (9)
N6—Cu—N3—C5	−83.1 (10)	C4—N3—C5—N4	1.5 (11)
N8—Cu—N3—C5	87.1 (10)	Cu—N3—C5—N4	178.1 (6)
N5—Cu—N3—C5	−134.3 (13)	C6—N4—C5—N3	−0.8 (11)
N2—Cu—N3—C5	−175.4 (10)	N3—C4—C6—N4	1.3 (10)
N9—Cu—N3—C5	9.0 (10)	C3—C4—C6—N4	−178.4 (9)
N6—Cu—N3—C4	93.2 (7)	N3—C4—C6—C7	−177.9 (10)
N8—Cu—N3—C4	−96.6 (6)	C3—C4—C6—C7	2.4 (18)
N5—Cu—N3—C4	42.0 (17)	C5—N4—C6—C4	−0.3 (10)
N2—Cu—N3—C4	1.0 (6)	C5—N4—C6—C7	179.0 (9)
N9—Cu—N3—C4	−174.7 (6)	C1—N1—C8—C9	138.9 (8)
N6—Cu—N5—C10	−6.0 (6)	C15—N1—C8—C9	−75.5 (9)
N3—Cu—N5—C10	46.3 (17)	C10—N5—C9—C8	−99.4 (9)
N8—Cu—N5—C10	−175.4 (6)	Cu—N5—C9—C8	73.2 (9)
N2—Cu—N5—C10	85.9 (6)	N1—C8—C9—N5	−55.6 (10)
N9—Cu—N5—C10	−96.9 (7)	C9—N5—C10—C11	179.5 (7)
N6—Cu—N5—C9	−178.7 (8)	Cu—N5—C10—C11	5.9 (10)
N3—Cu—N5—C9	−126.4 (13)	C12—N6—C11—C13	−0.6 (10)
N8—Cu—N5—C9	11.9 (7)	Cu—N6—C11—C13	178.1 (6)
N2—Cu—N5—C9	−86.8 (7)	C12—N6—C11—C10	178.0 (8)
N9—Cu—N5—C9	90.4 (7)	Cu—N6—C11—C10	−3.3 (9)
N3—Cu—N6—C12	13.2 (12)	N5—C10—C11—N6	−1.8 (11)
N8—Cu—N6—C12	−103.4 (19)	N5—C10—C11—C13	176.5 (9)
N5—Cu—N6—C12	−177.3 (12)	C11—N6—C12—N7	1.5 (11)
N2—Cu—N6—C12	88.6 (12)	Cu—N6—C12—N7	−176.6 (8)
N9—Cu—N6—C12	−81.2 (12)	C13—N7—C12—N6	−1.9 (12)
N3—Cu—N6—C11	−164.7 (6)	C12—N7—C13—C11	1.4 (10)
N8—Cu—N6—C11	78.6 (19)	C12—N7—C13—C14	−179.9 (9)
N5—Cu—N6—C11	4.8 (6)	N6—C11—C13—N7	−0.5 (10)
N2—Cu—N6—C11	−89.4 (6)	C10—C11—C13—N7	−178.8 (9)
N9—Cu—N6—C11	100.9 (6)	N6—C11—C13—C14	−179.1 (9)
N6—Cu—N8—C17	19 (2)	C10—C11—C13—C14	2.6 (17)
N3—Cu—N8—C17	−97.6 (6)	C1—N1—C15—C16	−85.4 (9)
N5—Cu—N8—C17	91.2 (6)	C8—N1—C15—C16	128.4 (8)
N2—Cu—N8—C17	−173.3 (6)	C17—N8—C16—C15	−104.7 (9)
N9—Cu—N8—C17	−3.9 (6)	Cu—N8—C16—C15	76.4 (8)
N6—Cu—N8—C16	−162.2 (15)	N1—C15—C16—N8	−60.3 (9)
N3—Cu—N8—C16	81.4 (7)	C16—N8—C17—C18	−178.2 (8)
N5—Cu—N8—C16	−89.8 (7)	Cu—N8—C17—C18	0.8 (11)
N2—Cu—N8—C16	5.7 (7)	N8—C17—C18—N9	5.9 (14)
N9—Cu—N8—C16	175.1 (7)	N8—C17—C18—C20	−178.5 (9)
N6—Cu—N9—C19	0.8 (16)	C19—N9—C18—C17	176.7 (8)
N3—Cu—N9—C19	−91.0 (16)	Cu—N9—C18—C17	−7.8 (10)
N8—Cu—N9—C19	176.6 (16)	C19—N9—C18—C20	0.3 (11)
N5—Cu—N9—C19	81.1 (16)	Cu—N9—C18—C20	175.9 (6)
N2—Cu—N9—C19	−113.3 (18)	C20—N10—C19—N9	−1.4 (12)
N6—Cu—N9—C18	−169.8 (6)	C18—N9—C19—N10	0.6 (11)
N3—Cu—N9—C18	98.5 (6)	Cu—N9—C19—N10	−169.8 (11)
N8—Cu—N9—C18	6.0 (6)	C19—N10—C20—C18	1.6 (10)
N5—Cu—N9—C18	−89.4 (6)	C19—N10—C20—C21	−179.1 (9)
N2—Cu—N9—C18	76.2 (16)	C17—C18—C20—N10	−177.0 (9)
C8—N1—C1—C2	−81.2 (9)	N9—C18—C20—N10	−1.1 (10)
C15—N1—C1—C2	133.3 (8)	C17—C18—C20—C21	3.7 (17)
C3—N2—C2—C1	−104.3 (9)	N9—C18—C20—C21	179.6 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—NH4···O6^i	0.86	2.09	2.930 (13)	165
N7—NH7···O8^ii	0.86	2.12	2.937 (14)	157
N10—NH10···O8^iii	0.86	2.14	2.993 (14)	172

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