Crystal structure of a mononuclear copper(II) complex with 2-methoxy-N,N-bis­(quinolin-2-yl­meth­yl)­ethyl­amine (DQMEA)

The crystal structure of [Cu(DQMEA)(CH₃CN)](ClO₄)₂ (DQMEA = N,N-bis­(2-quinolylmeth­yl)meth­oxy­ethyl­amine) has been determined. The structure reveals a five-coordinate Cu^II center with a distorted square-pyramidal geometry.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.050
• wR factor = 0.141
• Data-to-parameter ratio = 23.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min).         11 Note

Alert level C
PLAT220_ALERT_2_C Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        3.2 Ratio
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        Cl1 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C24 Check
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of        Cl2 Check
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.1 Note
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A      ..O3               2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5       ..O5               2.87 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6       ..O5               2.70 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9       ..O5A              2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10      ..O2               2.77 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10      ..O8A              2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11      ..O8               2.85 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13A     ..O8               2.70 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15      ..O2               2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H20      ..O6               2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21      ..O6               2.64 Ang.
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........          . Check
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........          . Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         14 Report

Alert level G
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          5 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT230_ALERT_2_G Hirshfeld Test Diff for   Cl1      --O2A       .       40.0 s.u.
PLAT231_ALERT_4_G Hirshfeld Test (Solvent)  Cl2      --O9        .        5.8 s.u.
PLAT231_ALERT_4_G Hirshfeld Test (Solvent)  Cl2      --O6A       .       26.5 s.u.
PLAT231_ALERT_4_G Hirshfeld Test (Solvent)  Cl2      --O7A       .       17.9 s.u.
PLAT231_ALERT_4_G Hirshfeld Test (Solvent)  Cl2      --O8A       .       17.0 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Cu1      --N4        .        7.1 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )         6% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )        60% Note
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #        137 Check
              O8A  -CL2  -O7A     1.555   1.555   1.555             39.60 Deg.
PLAT794_ALERT_5_G Tentative Bond Valency for Cu1       (II)      .       2.17 Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600       1017 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...         12 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
  19 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  17 ALERT level G = General information/check it is not something unexpected

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

---

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: ShelXT (Sheldrick, 2015b); program(s) used to refine structure: SHELXL (Sheldrick, 2015a); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(Acetonitrile)[2-methoxy-N,N-bis(quinolin-2-ylmethyl)ethylamine]copper(II) bis(perchlorate)

Crystal data

[Cu(C2H3N)(C23H23N3O)](ClO4)2	F(000) = 1356
Mr = 660.94	Dx = 1.573 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.3597 (3) Å	Cell parameters from 4574 reflections
b = 16.9611 (4) Å	θ = 3.4–30.8°
c = 14.5514 (3) Å	µ = 1.03 mm^−1
β = 95.622 (2)°	T = 293 K
V = 2790.18 (11) Å^3	Prism, blue
Z = 4	0.26 × 0.16 × 0.12 mm

Data collection

Rigaku Oxford Diffraction Gemini Eos diffractometer	9280 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	6238 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 16.0416 pixels mm^-1	θmax = 32.8°, θmin = 3.2°
ω scans	h = −17→17
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2015)	k = −25→16
Tmin = 0.883, Tmax = 1.000	l = −22→20
21447 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.141	w = 1/[σ^2(Fo^2) + (0.0599P)^2 + 1.6959P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.002
9280 reflections	Δρmax = 0.63 e Å^−3
392 parameters	Δρmin = −0.62 e Å^−3
0 restraints

Special details

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.55099 (2)	0.71839 (2)	0.33686 (2)	0.03253 (9)
O1	0.75176 (16)	0.75392 (12)	0.33841 (14)	0.0470 (4)
N1	0.55979 (18)	0.79512 (12)	0.44173 (14)	0.0367 (4)
N2	0.51058 (16)	0.81527 (11)	0.25797 (13)	0.0336 (4)
N3	0.59144 (16)	0.64254 (11)	0.44274 (13)	0.0322 (4)
N4	0.49754 (19)	0.63548 (13)	0.24774 (14)	0.0415 (5)
C1	0.6863 (2)	0.81542 (16)	0.4695 (2)	0.0463 (6)
H1A	0.721959	0.773908	0.508802	0.056*
H1B	0.689753	0.863821	0.505207	0.056*
C2	0.7563 (2)	0.82575 (17)	0.3879 (2)	0.0507 (7)
H2A	0.722827	0.867986	0.348680	0.061*
H2B	0.837625	0.839065	0.408536	0.061*
C3	0.4872 (3)	0.86476 (15)	0.41151 (19)	0.0466 (6)
H3A	0.521876	0.911629	0.441284	0.056*
H3B	0.408261	0.858502	0.430467	0.056*
C4	0.4795 (2)	0.87510 (14)	0.30860 (18)	0.0389 (5)
C5	0.4372 (2)	0.94704 (16)	0.2706 (2)	0.0483 (6)
H5	0.419262	0.988444	0.308724	0.058*
C6	0.4228 (2)	0.95522 (16)	0.1773 (2)	0.0488 (6)
H6	0.392258	1.001824	0.151054	0.059*
C7	0.4541 (2)	0.89326 (15)	0.12037 (19)	0.0397 (5)
C8	0.4441 (2)	0.89886 (18)	0.0231 (2)	0.0497 (7)
H8	0.411205	0.943900	−0.005389	0.060*
C9	0.4815 (3)	0.83981 (18)	−0.0292 (2)	0.0512 (7)
H9	0.472685	0.843926	−0.093188	0.061*
C10	0.5335 (2)	0.77235 (17)	0.01305 (19)	0.0458 (6)
H10	0.561192	0.732642	−0.023301	0.055*
C11	0.5441 (2)	0.76417 (15)	0.10707 (18)	0.0390 (5)
H11	0.579267	0.719209	0.134112	0.047*
C12	0.50211 (19)	0.82345 (13)	0.16290 (16)	0.0332 (4)
C13	0.5108 (2)	0.75237 (16)	0.51870 (17)	0.0426 (5)
H13A	0.425154	0.751374	0.508990	0.051*
H13B	0.533815	0.778812	0.576811	0.051*
C14	0.5585 (2)	0.67007 (15)	0.52143 (16)	0.0366 (5)
C15	0.5679 (2)	0.62524 (17)	0.60341 (17)	0.0451 (6)
H15	0.545784	0.646621	0.658017	0.054*
C16	0.6095 (2)	0.55061 (17)	0.60134 (18)	0.0461 (6)
H16	0.612713	0.519495	0.654150	0.055*
C17	0.6478 (2)	0.52007 (14)	0.52018 (17)	0.0385 (5)
C18	0.6968 (2)	0.44325 (16)	0.5147 (2)	0.0486 (7)
H18	0.699525	0.409785	0.565488	0.058*
C19	0.7394 (3)	0.41860 (17)	0.4359 (2)	0.0539 (7)
H19	0.769698	0.367859	0.432606	0.065*
C20	0.7383 (2)	0.46862 (16)	0.3597 (2)	0.0478 (6)
H20	0.770800	0.451518	0.306934	0.057*
C21	0.6902 (2)	0.54223 (15)	0.36142 (17)	0.0386 (5)
H21	0.689727	0.574828	0.309996	0.046*
C22	0.64130 (19)	0.56881 (13)	0.44086 (16)	0.0332 (4)
C23	0.8218 (3)	0.7556 (3)	0.2623 (2)	0.0666 (9)
H23A	0.824998	0.703717	0.236289	0.100*
H23B	0.900357	0.772868	0.283065	0.100*
H23C	0.787033	0.791379	0.216179	0.100*
C24	0.4563 (3)	0.58873 (19)	0.2001 (2)	0.0513 (7)
C25	0.4030 (5)	0.5283 (3)	0.1392 (3)	0.1066 (17)
H25A	0.403103	0.545212	0.076221	0.160*
H25B	0.323120	0.519299	0.152765	0.160*
H25C	0.447537	0.480328	0.148139	0.160*
Cl1	0.21788 (6)	0.71417 (6)	0.27686 (5)	0.0607 (2)
O2	0.1175 (4)	0.7570 (4)	0.2958 (3)	0.131 (2)	0.900 (10)
O2A	0.176 (4)	0.804 (4)	0.301 (3)	0.131 (2)	0.100 (10)
O3	0.2582 (2)	0.73903 (19)	0.19302 (15)	0.0759 (8)
O4	0.31026 (19)	0.72130 (14)	0.35046 (14)	0.0593 (6)
O5	0.1964 (8)	0.6280 (5)	0.2656 (5)	0.120 (3)	0.779 (16)
O5A	0.144 (3)	0.6625 (17)	0.2953 (18)	0.120 (3)	0.221 (16)
Cl2	0.23843 (8)	0.43937 (5)	0.92382 (6)	0.0615 (2)
O6	0.2005 (11)	0.4593 (6)	0.8369 (4)	0.199 (4)	0.681 (7)
O6A	0.132 (2)	0.4040 (13)	0.8829 (9)	0.199 (4)	0.319 (7)
O7	0.3251 (8)	0.4841 (5)	0.8889 (7)	0.164 (3)	0.652 (7)
O7A	0.3697 (14)	0.4290 (10)	0.9530 (13)	0.164 (3)	0.348 (7)
O8	0.2279 (7)	0.3596 (3)	0.9373 (5)	0.130 (3)	0.700 (7)
O8A	0.3117 (19)	0.3946 (7)	0.9791 (12)	0.130 (3)	0.300 (7)
O9	0.1885 (3)	0.48505 (17)	0.9896 (2)	0.0946 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.04023 (16)	0.02837 (14)	0.02880 (14)	0.00429 (11)	0.00239 (10)	0.00066 (11)
O1	0.0397 (9)	0.0505 (10)	0.0513 (11)	0.0031 (8)	0.0075 (8)	0.0029 (9)
N1	0.0433 (11)	0.0329 (10)	0.0334 (10)	0.0046 (8)	0.0011 (8)	−0.0026 (8)
N2	0.0336 (9)	0.0309 (9)	0.0360 (10)	0.0039 (7)	0.0019 (7)	0.0020 (8)
N3	0.0352 (9)	0.0329 (9)	0.0279 (8)	−0.0001 (7)	0.0009 (7)	0.0015 (7)
N4	0.0485 (12)	0.0384 (10)	0.0363 (10)	0.0044 (9)	−0.0021 (9)	0.0012 (9)
C1	0.0501 (14)	0.0392 (13)	0.0479 (14)	−0.0032 (11)	−0.0042 (11)	−0.0070 (12)
C2	0.0440 (14)	0.0449 (14)	0.0618 (18)	−0.0057 (12)	−0.0021 (12)	0.0057 (13)
C3	0.0605 (16)	0.0357 (12)	0.0436 (14)	0.0153 (12)	0.0050 (12)	−0.0049 (11)
C4	0.0360 (11)	0.0347 (11)	0.0456 (13)	0.0077 (9)	0.0018 (10)	0.0000 (10)
C5	0.0489 (14)	0.0372 (12)	0.0583 (17)	0.0158 (11)	0.0036 (12)	−0.0011 (12)
C6	0.0442 (14)	0.0376 (13)	0.0631 (17)	0.0127 (11)	−0.0026 (12)	0.0099 (12)
C7	0.0285 (10)	0.0396 (12)	0.0497 (14)	0.0015 (9)	−0.0033 (9)	0.0095 (11)
C8	0.0444 (14)	0.0549 (16)	0.0470 (14)	0.0005 (12)	−0.0094 (11)	0.0176 (13)
C9	0.0503 (15)	0.0609 (17)	0.0404 (14)	−0.0093 (13)	−0.0053 (11)	0.0104 (13)
C10	0.0488 (14)	0.0499 (15)	0.0387 (13)	−0.0065 (12)	0.0046 (11)	−0.0004 (12)
C11	0.0426 (12)	0.0356 (11)	0.0388 (12)	−0.0006 (10)	0.0047 (10)	0.0040 (10)
C12	0.0281 (10)	0.0339 (11)	0.0373 (11)	−0.0016 (8)	0.0017 (8)	0.0034 (9)
C13	0.0505 (14)	0.0468 (13)	0.0310 (11)	0.0038 (12)	0.0063 (10)	−0.0066 (11)
C14	0.0361 (11)	0.0415 (12)	0.0317 (11)	−0.0038 (9)	0.0011 (9)	−0.0006 (10)
C15	0.0513 (14)	0.0561 (15)	0.0273 (11)	−0.0071 (12)	0.0015 (10)	0.0016 (11)
C16	0.0504 (14)	0.0526 (15)	0.0333 (12)	−0.0120 (12)	−0.0055 (10)	0.0145 (11)
C17	0.0362 (11)	0.0364 (11)	0.0404 (12)	−0.0066 (9)	−0.0090 (9)	0.0075 (10)
C18	0.0454 (14)	0.0374 (12)	0.0590 (17)	−0.0055 (11)	−0.0156 (12)	0.0149 (12)
C19	0.0480 (15)	0.0367 (13)	0.073 (2)	0.0064 (11)	−0.0151 (14)	0.0009 (14)
C20	0.0427 (13)	0.0437 (14)	0.0554 (16)	0.0095 (11)	−0.0040 (11)	−0.0063 (12)
C21	0.0363 (11)	0.0381 (12)	0.0403 (12)	0.0030 (10)	−0.0020 (9)	0.0007 (10)
C22	0.0313 (10)	0.0317 (10)	0.0352 (11)	−0.0021 (8)	−0.0038 (8)	0.0031 (9)
C23	0.0497 (17)	0.090 (2)	0.062 (2)	0.0048 (17)	0.0169 (14)	0.0101 (19)
C24	0.0553 (16)	0.0592 (17)	0.0383 (13)	−0.0059 (14)	−0.0014 (11)	−0.0038 (13)
C25	0.121 (4)	0.123 (4)	0.073 (3)	−0.044 (3)	0.001 (3)	−0.048 (3)
Cl1	0.0402 (3)	0.0946 (6)	0.0459 (4)	−0.0098 (4)	−0.0030 (3)	0.0243 (4)
O2	0.053 (2)	0.254 (6)	0.091 (2)	0.053 (3)	0.0304 (18)	0.067 (3)
O2A	0.053 (2)	0.254 (6)	0.091 (2)	0.053 (3)	0.0304 (18)	0.067 (3)
O3	0.0582 (13)	0.126 (2)	0.0432 (12)	0.0025 (14)	0.0045 (10)	0.0245 (14)
O4	0.0571 (12)	0.0754 (15)	0.0433 (11)	−0.0029 (10)	−0.0054 (9)	0.0094 (10)
O5	0.154 (6)	0.092 (4)	0.105 (4)	−0.068 (4)	−0.031 (4)	0.007 (3)
O5A	0.154 (6)	0.092 (4)	0.105 (4)	−0.068 (4)	−0.031 (4)	0.007 (3)
Cl2	0.0803 (5)	0.0500 (4)	0.0570 (4)	−0.0022 (4)	0.0211 (4)	−0.0034 (4)
O6	0.324 (12)	0.213 (8)	0.058 (3)	0.033 (8)	0.004 (4)	0.030 (4)
O6A	0.324 (12)	0.213 (8)	0.058 (3)	0.033 (8)	0.004 (4)	0.030 (4)
O7	0.162 (6)	0.138 (6)	0.213 (9)	−0.031 (5)	0.126 (7)	−0.003 (5)
O7A	0.162 (6)	0.138 (6)	0.213 (9)	−0.031 (5)	0.126 (7)	−0.003 (5)
O8	0.202 (7)	0.047 (2)	0.154 (5)	0.018 (3)	0.078 (5)	0.004 (3)
O8A	0.202 (7)	0.047 (2)	0.154 (5)	0.018 (3)	0.078 (5)	0.004 (3)
O9	0.109 (2)	0.0719 (17)	0.110 (2)	−0.0034 (16)	0.0437 (18)	−0.0223 (17)

Geometric parameters (Å, º)

Cu1—O1	2.3570 (19)	C13—H13B	0.9700
Cu1—N1	2.001 (2)	C13—C14	1.496 (4)
Cu1—N2	2.0311 (19)	C14—C15	1.410 (3)
Cu1—N3	2.0251 (18)	C15—H15	0.9300
Cu1—N4	1.968 (2)	C15—C16	1.353 (4)
O1—C2	1.414 (4)	C16—H16	0.9300
O1—C23	1.426 (4)	C16—C17	1.397 (4)
N1—C1	1.494 (3)	C17—C18	1.422 (4)
N1—C3	1.482 (3)	C17—C22	1.416 (3)
N1—C13	1.487 (3)	C18—H18	0.9300
N2—C4	1.322 (3)	C18—C19	1.353 (5)
N2—C12	1.384 (3)	C19—H19	0.9300
N3—C14	1.324 (3)	C19—C20	1.396 (4)
N3—C22	1.374 (3)	C20—H20	0.9300
N4—C24	1.124 (3)	C20—C21	1.364 (4)
C1—H1A	0.9700	C21—H21	0.9300
C1—H1B	0.9700	C21—C22	1.405 (3)
C1—C2	1.503 (4)	C23—H23A	0.9600
C2—H2A	0.9700	C23—H23B	0.9600
C2—H2B	0.9700	C23—H23C	0.9600
C3—H3A	0.9700	C24—C25	1.449 (5)
C3—H3B	0.9700	C25—H25A	0.9600
C3—C4	1.502 (4)	C25—H25B	0.9600
C4—C5	1.405 (3)	C25—H25C	0.9600
C5—H5	0.9300	Cl1—O2	1.402 (4)
C5—C6	1.359 (4)	Cl1—O2A	1.65 (6)
C6—H6	0.9300	Cl1—O3	1.409 (2)
C6—C7	1.405 (4)	Cl1—O4	1.429 (2)
C7—C8	1.412 (4)	Cl1—O5	1.489 (8)
C7—C12	1.420 (3)	Cl1—O5A	1.26 (2)
C8—H8	0.9300	Cl2—O6	1.339 (6)
C8—C9	1.351 (4)	Cl2—O6A	1.43 (2)
C9—H9	0.9300	Cl2—O7	1.379 (6)
C9—C10	1.402 (4)	Cl2—O7A	1.520 (18)
C10—H10	0.9300	Cl2—O8	1.375 (5)
C10—C11	1.369 (4)	Cl2—O8A	1.336 (17)
C11—H11	0.9300	Cl2—O9	1.394 (3)
C11—C12	1.405 (3)	O6—O7	1.595 (12)
C13—H13A	0.9700	O7A—O8A	0.984 (17)
N1—Cu1—O1	81.40 (8)	N1—C13—H13B	110.0
N1—Cu1—N2	84.06 (8)	N1—C13—C14	108.3 (2)
N1—Cu1—N3	80.92 (8)	H13A—C13—H13B	108.4
N2—Cu1—O1	87.91 (7)	C14—C13—H13A	110.0
N3—Cu1—O1	90.45 (7)	C14—C13—H13B	110.0
N3—Cu1—N2	164.97 (8)	N3—C14—C13	116.0 (2)
N4—Cu1—O1	115.14 (8)	N3—C14—C15	122.5 (2)
N4—Cu1—N1	163.04 (9)	C15—C14—C13	121.5 (2)
N4—Cu1—N2	99.65 (8)	C14—C15—H15	120.5
N4—Cu1—N3	94.57 (8)	C16—C15—C14	118.9 (2)
C2—O1—Cu1	102.24 (15)	C16—C15—H15	120.5
C2—O1—C23	112.5 (3)	C15—C16—H16	119.9
C23—O1—Cu1	127.62 (19)	C15—C16—C17	120.3 (2)
C1—N1—Cu1	109.34 (15)	C17—C16—H16	119.9
C3—N1—Cu1	107.90 (15)	C16—C17—C18	122.9 (2)
C3—N1—C1	112.9 (2)	C16—C17—C22	118.5 (2)
C3—N1—C13	112.0 (2)	C22—C17—C18	118.6 (3)
C13—N1—Cu1	105.24 (15)	C17—C18—H18	119.8
C13—N1—C1	109.2 (2)	C19—C18—C17	120.3 (3)
C4—N2—Cu1	111.34 (16)	C19—C18—H18	119.8
C4—N2—C12	118.9 (2)	C18—C19—H19	119.7
C12—N2—Cu1	129.47 (16)	C18—C19—C20	120.6 (3)
C14—N3—Cu1	111.82 (16)	C20—C19—H19	119.7
C14—N3—C22	119.3 (2)	C19—C20—H20	119.5
C22—N3—Cu1	128.77 (15)	C21—C20—C19	120.9 (3)
C24—N4—Cu1	173.1 (2)	C21—C20—H20	119.5
N1—C1—H1A	109.1	C20—C21—H21	120.0
N1—C1—H1B	109.1	C20—C21—C22	120.0 (2)
N1—C1—C2	112.5 (2)	C22—C21—H21	120.0
H1A—C1—H1B	107.8	N3—C22—C17	120.2 (2)
C2—C1—H1A	109.1	N3—C22—C21	120.4 (2)
C2—C1—H1B	109.1	C21—C22—C17	119.4 (2)
O1—C2—C1	107.9 (2)	O1—C23—H23A	109.5
O1—C2—H2A	110.1	O1—C23—H23B	109.5
O1—C2—H2B	110.1	O1—C23—H23C	109.5
C1—C2—H2A	110.1	H23A—C23—H23B	109.5
C1—C2—H2B	110.1	H23A—C23—H23C	109.5
H2A—C2—H2B	108.4	H23B—C23—H23C	109.5
N1—C3—H3A	109.3	N4—C24—C25	179.7 (4)
N1—C3—H3B	109.3	C24—C25—H25A	109.5
N1—C3—C4	111.4 (2)	C24—C25—H25B	109.5
H3A—C3—H3B	108.0	C24—C25—H25C	109.5
C4—C3—H3A	109.3	H25A—C25—H25B	109.5
C4—C3—H3B	109.3	H25A—C25—H25C	109.5
N2—C4—C3	118.3 (2)	H25B—C25—H25C	109.5
N2—C4—C5	123.2 (2)	O2—Cl1—O3	110.8 (2)
C5—C4—C3	118.6 (2)	O2—Cl1—O4	111.1 (2)
C4—C5—H5	120.5	O2—Cl1—O5	113.7 (5)
C6—C5—C4	119.0 (3)	O3—Cl1—O2A	91.7 (14)
C6—C5—H5	120.5	O3—Cl1—O4	110.24 (14)
C5—C6—H6	120.0	O3—Cl1—O5	105.2 (4)
C5—C6—C7	120.0 (2)	O4—Cl1—O2A	88.1 (16)
C7—C6—H6	120.0	O4—Cl1—O5	105.4 (3)
C6—C7—C8	122.7 (2)	O5A—Cl1—O2A	113 (3)
C6—C7—C12	118.4 (2)	O5A—Cl1—O3	132.2 (12)
C8—C7—C12	118.9 (2)	O5A—Cl1—O4	110.9 (11)
C7—C8—H8	119.5	O6—Cl2—O7	71.9 (6)
C9—C8—C7	121.0 (3)	O6—Cl2—O8	111.1 (6)
C9—C8—H8	119.5	O6—Cl2—O9	113.1 (4)
C8—C9—H9	120.0	O6A—Cl2—O7A	146.7 (10)
C8—C9—C10	120.0 (3)	O7—Cl2—O9	107.5 (4)
C10—C9—H9	120.0	O8—Cl2—O7	132.0 (4)
C9—C10—H10	119.6	O8—Cl2—O9	113.7 (3)
C11—C10—C9	120.9 (3)	O8A—Cl2—O6A	117.7 (11)
C11—C10—H10	119.6	O8A—Cl2—O7A	39.6 (8)
C10—C11—H11	119.9	O8A—Cl2—O9	100.0 (6)
C10—C11—C12	120.2 (2)	O9—Cl2—O6A	97.7 (8)
C12—C11—H11	119.9	O9—Cl2—O7A	109.1 (6)
N2—C12—C7	120.4 (2)	Cl2—O6—O7	55.2 (4)
N2—C12—C11	120.8 (2)	Cl2—O7—O6	52.9 (4)
C11—C12—C7	118.8 (2)	O8A—O7A—Cl2	60.1 (15)
N1—C13—H13A	110.0	O7A—O8A—Cl2	80.3 (16)
Cu1—O1—C2—C1	43.6 (2)	C9—C10—C11—C12	0.4 (4)
Cu1—N1—C1—C2	40.5 (3)	C10—C11—C12—N2	178.9 (2)
Cu1—N1—C3—C4	−26.8 (3)	C10—C11—C12—C7	−3.1 (3)
Cu1—N1—C13—C14	42.2 (2)	C12—N2—C4—C3	179.0 (2)
Cu1—N2—C4—C3	4.3 (3)	C12—N2—C4—C5	0.5 (4)
Cu1—N2—C4—C5	−174.2 (2)	C12—C7—C8—C9	−1.3 (4)
Cu1—N2—C12—C7	169.80 (16)	C13—N1—C1—C2	155.2 (2)
Cu1—N2—C12—C11	−12.2 (3)	C13—N1—C3—C4	−142.2 (2)
Cu1—N3—C14—C13	−5.9 (3)	C13—C14—C15—C16	178.8 (2)
Cu1—N3—C14—C15	174.49 (19)	C14—N3—C22—C17	5.5 (3)
Cu1—N3—C22—C17	−171.17 (16)	C14—N3—C22—C21	−172.1 (2)
Cu1—N3—C22—C21	11.2 (3)	C14—C15—C16—C17	3.0 (4)
N1—C1—C2—O1	−60.0 (3)	C15—C16—C17—C18	177.4 (2)
N1—C3—C4—N2	15.5 (3)	C15—C16—C17—C22	−0.3 (4)
N1—C3—C4—C5	−166.0 (2)	C16—C17—C18—C19	−175.7 (2)
N1—C13—C14—N3	−24.7 (3)	C16—C17—C22—N3	−4.0 (3)
N1—C13—C14—C15	154.9 (2)	C16—C17—C22—C21	173.6 (2)
N2—C4—C5—C6	2.6 (4)	C17—C18—C19—C20	1.4 (4)
N3—C14—C15—C16	−1.6 (4)	C18—C17—C22—N3	178.1 (2)
C1—N1—C3—C4	94.1 (3)	C18—C17—C22—C21	−4.2 (3)
C1—N1—C13—C14	−75.1 (2)	C18—C19—C20—C21	−2.6 (4)
C3—N1—C1—C2	−79.6 (3)	C19—C20—C21—C22	0.3 (4)
C3—N1—C13—C14	159.2 (2)	C20—C21—C22—N3	−179.2 (2)
C3—C4—C5—C6	−175.9 (3)	C20—C21—C22—C17	3.1 (3)
C4—N2—C12—C7	−3.8 (3)	C22—N3—C14—C13	176.9 (2)
C4—N2—C12—C11	174.2 (2)	C22—N3—C14—C15	−2.7 (3)
C4—C5—C6—C7	−2.2 (4)	C22—C17—C18—C19	2.0 (4)
C5—C6—C7—C8	−178.4 (3)	C23—O1—C2—C1	−176.4 (2)
C5—C6—C7—C12	−0.9 (4)	O6A—Cl2—O7A—O8A	−59 (2)
C6—C7—C8—C9	176.1 (3)	O6A—Cl2—O8A—O7A	147.8 (14)
C6—C7—C12—N2	4.0 (3)	O8—Cl2—O6—O7	−129.0 (5)
C6—C7—C12—C11	−174.0 (2)	O8—Cl2—O7—O6	102.4 (7)
C7—C8—C9—C10	−1.4 (4)	O9—Cl2—O6—O7	101.7 (5)
C8—C7—C12—N2	−178.4 (2)	O9—Cl2—O7—O6	−109.3 (5)
C8—C7—C12—C11	3.5 (3)	O9—Cl2—O7A—O8A	82.6 (13)
C8—C9—C10—C11	1.9 (4)	O9—Cl2—O8A—O7A	−107.9 (12)

Hydrogen-bond geometry (Å, º)

Cg4, Cg5, Cg6 and Cg7 are the centroids of the N2/C4–C7/C12, N3/C14–C17/C22, C7–C12 and C17–C22 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O3^i	0.97	2.68	3.402 (4)	132
C1—H1B···O9^ii	0.97	2.57	3.397 (4)	143
C3—H3B···O8^iii	0.97	2.58	3.446 (6)	148
C5—H5···O5^iv	0.93	2.87	3.441 (6)	121
C6—H6···O5^iv	0.93	2.70	3.366 (6)	129
C9—H9···O5A^ii	0.93	2.65	3.29 (4)	127
C10—H10···O2^ii	0.93	2.77	3.427 (5)	128
C10—H10···O8A^v	0.93	2.64	3.329 (13)	131
C11—H11···N4	0.93	2.43	3.074 (3)	126
C11—H11···O8^v	0.93	2.85	3.443 (6)	123
C13—H13A···O4	0.97	2.59	3.220 (3)	123
C13—H13A···O8^iii	0.97	2.70	3.378 (7)	128
C15—H15···O2^i	0.93	2.65	3.440 (5)	143
C15—H15···O2A^i	0.93	2.57	3.24 (3)	129
C18—H18···O4^v	0.93	2.55	3.417 (3)	156
C20—H20···O6^v	0.93	2.63	3.248 (8)	125
C21—H21···O6^v	0.93	2.64	3.252 (8)	124
C23—H23B···O2^vi	0.96	2.47	3.347 (6)	152
C8—H8···Cg7^vii	0.93	2.75	3.511 (3)	139
C19—H19···Cg6^viii	0.93	2.76	3.377 (3)	125
Cl1—O3···Cg4		3.43 (1)	4.2079 (13)	114 (1)
Cl1—O2A···Cg4		3.90 (5)	4.2079 (13)	89 (2)
Cg5···Cg5^v			4.0264 (14)
Cg5···Cg7^v			3.7767 (14)

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