Chloro­bis(1,10-phenanthroline)copper(II) chloride methanol solvate 4.5-hydrate

In the title compound, [CuCl(C₁₂H₈N₂)₂]Cl·CH₃OH·4.5H₂O, the coordination geometry around the Cu atom is that of a trigonal bipyramid, with the central Cu atom bound to one Cl atom and four N atoms of the two phenanthroline ligands. The dihedral angle between the two phenanthroline planes is 49.6 (1)°; the dihedral angles between these planes and the equatorial plane of the trigonal bipyramid are 79.2 (1) and 88.4 (1)°.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.011 Å
• R factor = 0.097
• wR factor = 0.279
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT413_ALERT_2_A Short Inter XH3 .. XHn     H20    ..  H25B    ..       1.65 Ang.
PLAT432_ALERT_2_A Short Inter X...Y Contact  O3W    ..  C25     ..       2.44 Ang.

Alert level B
PLAT214_ALERT_2_B Atom O2W     (Anion/Solvent) ADP max/min Ratio         5.60 prolat
PLAT413_ALERT_2_B Short Inter XH3 .. XHn     H11    ..  H25A    ..       2.05 Ang.
PLAT413_ALERT_2_B Short Inter XH3 .. XHn     H12    ..  H25B    ..       2.09 Ang.
PLAT415_ALERT_2_B Short Inter D-H..H-X       H3WB   ..  H25C    ..       2.07 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H1A    ..  H1A     ..       1.30 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H2WB   ..  H2WB    ..       1.33 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H4WA   ..  H5WA    ..       1.98 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H4WA   ..  H5WB    ..       1.68 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H5WA   ..  H6WA    ..       2.00 Ang.
PLAT420_ALERT_2_B D-H Without Acceptor       O5W    -   H5WA   ...          ?
PLAT431_ALERT_2_B Short Inter HL..A Contact  Cl1    ..  Cl2     ..       3.16 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  O4W    ..  C25     ..       2.75 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  O4W    ..  C25     ..       2.75 Ang.

Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.279
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT084_ALERT_2_C High R2 Value ..................................       0.28
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   N2      ..       5.69 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   N4      ..       5.25 su
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         11
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          9
            N4  -CU1 -N2  -C6     99.00  4.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         13
            N4  -CU1 -N2  -C12   -82.00  4.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         25
            N2  -CU1 -N4  -C24  -156.00  3.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         29
            N2  -CU1 -N4  -C18    35.00  4.00   1.555   1.555   1.555   1.555
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          9

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  18 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
   5 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: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1999); software used to prepare material for publication: SHELXTL/PC.

Chlorobis(1,10-phenanthroline)copper(II) chloride methanol 4.5-hydrate

Crystal data

[CuCl(C12H8N2)2]Cl·CH4O·4.5H2O	F(000) = 2512
Mr = 607.96	Dx = 1.552 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4822 reflections
a = 23.387 (5) Å	θ = 2.2–25.2°
b = 30.418 (7) Å	µ = 1.09 mm^−1
c = 7.3816 (16) Å	T = 173 K
β = 97.714 (3)°	Block, green
V = 5204 (2) Å^3	0.38 × 0.30 × 0.20 mm
Z = 8

Data collection

Bruker SMART 1K CCD area-detector diffractometer	4524 independent reflections
Radiation source: fine-focus sealed tube	3292 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
φ and ω scans	θmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −24→27
Tmin = 0.682, Tmax = 0.811	k = −36→36
12342 measured reflections	l = −8→5

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)] = 0.097	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.279	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.1394P)^2 + 34.1552P] where P = (Fo^2 + 2Fc^2)/3
4524 reflections	(Δ/σ)max = 0.001
343 parameters	Δρmax = 1.04 e Å^−3
0 restraints	Δρmin = −0.80 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
Cu1	0.77549 (4)	0.88115 (3)	0.34383 (12)	0.0464 (3)
N1	0.8107 (2)	0.9440 (2)	0.4049 (7)	0.0446 (13)
N2	0.7099 (3)	0.9169 (2)	0.2277 (8)	0.0487 (14)
N3	0.7271 (2)	0.84575 (19)	0.5120 (7)	0.0436 (12)
N4	0.8384 (3)	0.8448 (2)	0.4747 (8)	0.0516 (14)
Cl1	0.79099 (8)	0.85266 (6)	0.0583 (2)	0.0538 (5)
C1	0.8602 (3)	0.9574 (3)	0.4932 (10)	0.0536 (17)
H1	0.8871	0.9360	0.5456	0.064*
C2	0.8752 (3)	1.0024 (3)	0.5135 (11)	0.059 (2)
H2	0.9124	1.0105	0.5719	0.071*
C3	0.8371 (4)	1.0338 (3)	0.4505 (10)	0.0564 (19)
H3	0.8466	1.0640	0.4686	0.068*
C4	0.7825 (3)	1.0213 (2)	0.3567 (9)	0.0464 (16)
C5	0.7717 (3)	0.9757 (2)	0.3382 (8)	0.0414 (14)
C6	0.7179 (3)	0.9605 (2)	0.2432 (8)	0.0422 (14)
C7	0.7385 (4)	1.0514 (3)	0.2815 (11)	0.059 (2)
H7	0.7452	1.0821	0.2962	0.071*
C8	0.6876 (4)	1.0374 (3)	0.1900 (11)	0.063 (2)
H8	0.6598	1.0584	0.1401	0.075*
C9	0.6753 (3)	0.9917 (2)	0.1674 (10)	0.0488 (16)
C10	0.6235 (3)	0.9741 (3)	0.0731 (10)	0.060 (2)
H10	0.5937	0.9933	0.0204	0.072*
C11	0.6166 (3)	0.9292 (3)	0.0579 (12)	0.061 (2)
H11	0.5820	0.9173	−0.0054	0.073*
C12	0.6599 (3)	0.9018 (3)	0.1348 (11)	0.0564 (18)
H12	0.6545	0.8709	0.1223	0.068*
C13	0.6712 (3)	0.8469 (2)	0.5308 (10)	0.0514 (17)
H13	0.6478	0.8695	0.4710	0.062*
C14	0.6455 (3)	0.8156 (3)	0.6372 (10)	0.0564 (19)
H14	0.6056	0.8173	0.6493	0.068*
C15	0.6794 (3)	0.7827 (3)	0.7223 (10)	0.0565 (19)
H15	0.6630	0.7617	0.7951	0.068*
C16	0.7375 (3)	0.7801 (2)	0.7025 (9)	0.0492 (16)
C17	0.7604 (3)	0.8127 (2)	0.5978 (8)	0.0410 (14)
C18	0.8200 (3)	0.8120 (2)	0.5771 (9)	0.0448 (15)
C19	0.7757 (4)	0.7464 (2)	0.7852 (9)	0.0544 (18)
H19	0.7610	0.7239	0.8555	0.065*
C20	0.8327 (4)	0.7463 (2)	0.7637 (10)	0.0553 (18)
H20	0.8571	0.7237	0.8187	0.066*
C21	0.8562 (3)	0.7793 (2)	0.6612 (9)	0.0508 (16)
C22	0.9153 (3)	0.7809 (3)	0.6330 (11)	0.0589 (19)
H22	0.9419	0.7594	0.6865	0.071*
C23	0.9329 (3)	0.8134 (3)	0.5289 (11)	0.063 (2)
H23	0.9722	0.8145	0.5093	0.076*
C24	0.8948 (3)	0.8455 (3)	0.4490 (11)	0.0573 (18)
H24	0.9084	0.8679	0.3763	0.069*
C25	0.4385 (6)	0.1759 (5)	0.968 (2)	0.116 (4)
H25A	0.4375	0.1483	1.0354	0.174*
H25B	0.3992	0.1843	0.9168	0.174*
H25C	0.4555	0.1990	1.0503	0.174*
O1	0.4703 (4)	0.1706 (3)	0.8321 (13)	0.106 (3)
H1A	0.4762	0.1952	0.7862	0.159*
Cl2	0.0774 (3)	0.8361 (3)	0.4757 (10)	0.235 (3)
O1W	0.0000	0.0774 (5)	0.7500	0.117 (4)
H1WA	0.0098	0.0601	0.6691	0.048*
O2W	0.9883 (13)	0.0716 (16)	0.394 (8)	0.87 (7)
H2WA	0.9603	0.0894	0.3658	0.048*
H2WB	0.9866	0.0524	0.3238	0.048*
O3W	0.4512 (4)	0.2473 (5)	0.1189 (14)	0.170 (6)
H3WB	0.4514	0.2517	0.2265	0.048*
H3WA	0.4521	0.2702	0.0627	0.048*
O4W	0.5000	0.1300 (5)	0.2500	0.120 (4)
H4WA	0.4785	0.1145	0.3012	0.048*
O5W	0.0546 (4)	0.5847 (4)	−0.0333 (15)	0.133 (4)
H5WA	0.0459	0.5669	0.0425	0.048*
H5WB	0.0461	0.6094	−0.0033	0.048*
O6W	1.0000	0.5129 (9)	0.7500	0.200 (10)
H6WA	0.9808	0.5294	0.6742	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0447 (5)	0.0478 (6)	0.0478 (5)	−0.0010 (3)	0.0101 (4)	0.0028 (3)
N1	0.036 (3)	0.056 (3)	0.043 (3)	−0.002 (2)	0.010 (2)	0.002 (2)
N2	0.054 (3)	0.052 (3)	0.041 (3)	−0.014 (3)	0.010 (3)	−0.001 (2)
N3	0.040 (3)	0.052 (3)	0.040 (3)	−0.003 (2)	0.008 (2)	−0.005 (2)
N4	0.056 (4)	0.057 (4)	0.044 (3)	−0.010 (3)	0.014 (3)	−0.004 (3)
Cl1	0.0660 (11)	0.0501 (10)	0.0474 (9)	−0.0001 (8)	0.0152 (8)	−0.0026 (7)
C1	0.047 (4)	0.062 (5)	0.055 (4)	−0.009 (3)	0.020 (3)	0.001 (3)
C2	0.051 (4)	0.069 (5)	0.061 (4)	−0.023 (4)	0.023 (4)	−0.014 (4)
C3	0.070 (5)	0.052 (4)	0.051 (4)	−0.008 (4)	0.024 (4)	−0.007 (3)
C4	0.055 (4)	0.046 (4)	0.043 (3)	−0.004 (3)	0.025 (3)	0.002 (3)
C5	0.044 (3)	0.049 (4)	0.034 (3)	−0.003 (3)	0.013 (3)	−0.005 (3)
C6	0.031 (3)	0.062 (4)	0.036 (3)	0.000 (3)	0.013 (2)	0.004 (3)
C7	0.085 (6)	0.044 (4)	0.055 (4)	0.007 (4)	0.029 (4)	0.000 (3)
C8	0.071 (5)	0.071 (5)	0.050 (4)	0.008 (4)	0.020 (4)	0.008 (4)
C9	0.051 (4)	0.053 (4)	0.046 (4)	0.010 (3)	0.023 (3)	0.008 (3)
C10	0.046 (4)	0.088 (6)	0.049 (4)	0.004 (4)	0.015 (3)	0.010 (4)
C11	0.042 (4)	0.076 (6)	0.064 (5)	−0.002 (4)	0.002 (3)	0.009 (4)
C12	0.044 (4)	0.072 (5)	0.056 (4)	−0.005 (4)	0.014 (3)	0.010 (4)
C13	0.045 (4)	0.055 (4)	0.055 (4)	−0.005 (3)	0.013 (3)	−0.005 (3)
C14	0.052 (4)	0.068 (5)	0.053 (4)	−0.011 (4)	0.022 (3)	−0.008 (4)
C15	0.060 (5)	0.068 (5)	0.042 (4)	−0.019 (4)	0.008 (3)	0.004 (3)
C16	0.060 (4)	0.048 (4)	0.040 (3)	−0.010 (3)	0.009 (3)	−0.004 (3)
C17	0.049 (4)	0.039 (3)	0.037 (3)	−0.004 (3)	0.012 (3)	−0.007 (3)
C18	0.047 (4)	0.047 (4)	0.041 (3)	0.000 (3)	0.007 (3)	−0.004 (3)
C19	0.071 (5)	0.054 (4)	0.035 (3)	−0.013 (4)	−0.004 (3)	0.000 (3)
C20	0.067 (5)	0.047 (4)	0.050 (4)	−0.001 (3)	−0.002 (3)	0.001 (3)
C21	0.058 (4)	0.051 (4)	0.042 (4)	0.008 (3)	0.003 (3)	−0.002 (3)
C22	0.051 (4)	0.061 (5)	0.062 (4)	0.009 (4)	−0.004 (4)	−0.002 (4)
C23	0.041 (4)	0.087 (6)	0.062 (5)	0.010 (4)	0.012 (3)	−0.007 (4)
C24	0.047 (4)	0.062 (5)	0.066 (5)	0.003 (3)	0.018 (3)	0.003 (4)
C25	0.081 (8)	0.127 (11)	0.137 (12)	0.008 (8)	0.005 (8)	0.007 (9)
O1	0.107 (6)	0.090 (5)	0.113 (6)	−0.012 (5)	−0.016 (5)	0.037 (5)
Cl2	0.182 (6)	0.328 (10)	0.198 (6)	−0.017 (6)	0.034 (5)	0.060 (6)
O1W	0.053 (6)	0.194 (13)	0.108 (9)	0.000	0.020 (6)	0.000
O2W	0.22 (3)	0.99 (9)	1.32 (17)	−0.34 (5)	−0.19 (5)	0.84 (11)
O3W	0.078 (6)	0.303 (15)	0.118 (7)	−0.067 (7)	−0.023 (5)	0.112 (8)
O4W	0.086 (8)	0.138 (11)	0.141 (12)	0.000	0.027 (8)	0.000
O5W	0.089 (6)	0.152 (8)	0.154 (9)	0.047 (6)	0.001 (6)	−0.037 (7)
O6W	0.031 (5)	0.42 (3)	0.143 (13)	0.000	−0.001 (6)	0.000

Geometric parameters (Å, º)

Cu1—N2	1.979 (6)	C13—H13	0.9500
Cu1—N4	1.986 (7)	C14—C15	1.374 (12)
Cu1—N3	2.087 (5)	C14—H14	0.9500
Cu1—N1	2.105 (6)	C15—C16	1.388 (11)
Cu1—Cl1	2.351 (2)	C15—H15	0.9500
N1—C1	1.316 (9)	C16—C17	1.408 (9)
N1—C5	1.374 (9)	C16—C19	1.442 (11)
N2—C6	1.344 (9)	C17—C18	1.423 (9)
N2—C12	1.355 (9)	C18—C21	1.396 (10)
N3—C13	1.334 (9)	C19—C20	1.364 (11)
N3—C17	1.372 (9)	C19—H19	0.9500
N4—C24	1.357 (9)	C20—C21	1.411 (11)
N4—C18	1.355 (9)	C20—H20	0.9500
C1—C2	1.418 (11)	C21—C22	1.427 (11)
C1—H1	0.9500	C22—C23	1.350 (12)
C2—C3	1.345 (12)	C22—H22	0.9500
C2—H2	0.9500	C23—C24	1.398 (11)
C3—C4	1.421 (11)	C23—H23	0.9500
C3—H3	0.9500	C24—H24	0.9500
C4—C5	1.412 (9)	C25—O1	1.334 (15)
C4—C7	1.431 (11)	C25—H25A	0.9800
C5—C6	1.431 (9)	C25—H25B	0.9800
C6—C9	1.434 (9)	C25—H25C	0.9800
C7—C8	1.355 (12)	O1—H1A	0.8400
C7—H7	0.9500	O1W—H1WA	0.8497
C8—C9	1.423 (11)	O2W—H2WA	0.8535
C8—H8	0.9500	O2W—H2WB	0.7761
C9—C10	1.418 (11)	O3W—H3WB	0.8048
C10—C11	1.379 (12)	O3W—H3WA	0.8110
C10—H10	0.9500	O4W—H4WA	0.8188
C11—C12	1.375 (11)	O5W—H5WA	0.8226
C11—H11	0.9500	O5W—H5WB	0.8159
C12—H12	0.9500	O6W—H6WA	0.8356
C13—C14	1.419 (10)
N2—Cu1—N4	176.1 (2)	C10—C11—C12	119.7 (8)
N2—Cu1—N3	95.2 (2)	C10—C11—H11	120.2
N4—Cu1—N3	81.3 (2)	C12—C11—H11	120.2
N2—Cu1—N1	81.5 (2)	N2—C12—C11	122.8 (8)
N4—Cu1—N1	99.2 (2)	N2—C12—H12	118.6
N3—Cu1—N1	124.6 (2)	C11—C12—H12	118.6
N2—Cu1—Cl1	91.03 (17)	N3—C13—C14	122.3 (7)
N4—Cu1—Cl1	92.15 (18)	N3—C13—H13	118.9
N3—Cu1—Cl1	120.27 (16)	C14—C13—H13	118.9
N1—Cu1—Cl1	115.06 (16)	C15—C14—C13	118.7 (7)
C1—N1—C5	117.3 (6)	C15—C14—H14	120.7
C1—N1—Cu1	132.8 (5)	C13—C14—H14	120.7
C5—N1—Cu1	109.9 (4)	C14—C15—C16	120.4 (7)
C6—N2—C12	118.6 (7)	C14—C15—H15	119.8
C6—N2—Cu1	114.5 (4)	C16—C15—H15	119.8
C12—N2—Cu1	126.8 (5)	C15—C16—C17	117.9 (7)
C13—N3—C17	118.3 (6)	C15—C16—C19	123.8 (7)
C13—N3—Cu1	131.7 (5)	C17—C16—C19	118.3 (7)
C17—N3—Cu1	109.4 (4)	N3—C17—C16	122.3 (6)
C24—N4—C18	118.5 (7)	N3—C17—C18	117.7 (6)
C24—N4—Cu1	126.4 (5)	C16—C17—C18	119.9 (6)
C18—N4—Cu1	114.3 (5)	N4—C18—C21	123.6 (7)
N1—C1—C2	122.7 (8)	N4—C18—C17	115.9 (6)
N1—C1—H1	118.7	C21—C18—C17	120.5 (7)
C2—C1—H1	118.7	C20—C19—C16	120.8 (7)
C3—C2—C1	120.4 (8)	C20—C19—H19	119.6
C3—C2—H2	119.8	C16—C19—H19	119.6
C1—C2—H2	119.8	C19—C20—C21	121.2 (7)
C2—C3—C4	119.3 (7)	C19—C20—H20	119.4
C2—C3—H3	120.3	C21—C20—H20	119.4
C4—C3—H3	120.3	C18—C21—C20	119.3 (7)
C5—C4—C3	116.5 (7)	C18—C21—C22	116.9 (7)
C5—C4—C7	118.7 (7)	C20—C21—C22	123.7 (7)
C3—C4—C7	124.8 (7)	C23—C22—C21	118.8 (7)
N1—C5—C4	123.7 (6)	C23—C22—H22	120.6
N1—C5—C6	116.4 (6)	C21—C22—H22	120.6
C4—C5—C6	119.9 (6)	C22—C23—C24	121.8 (7)
N2—C6—C5	117.6 (6)	C22—C23—H23	119.1
N2—C6—C9	122.6 (6)	C24—C23—H23	119.1
C5—C6—C9	119.7 (7)	N4—C24—C23	120.4 (7)
C8—C7—C4	121.9 (8)	N4—C24—H24	119.8
C8—C7—H7	119.0	C23—C24—H24	119.8
C4—C7—H7	119.0	O1—C25—H25A	109.5
C7—C8—C9	121.1 (8)	O1—C25—H25B	109.5
C7—C8—H8	119.5	H25A—C25—H25B	109.5
C9—C8—H8	119.5	O1—C25—H25C	109.5
C8—C9—C10	124.9 (7)	H25A—C25—H25C	109.5
C8—C9—C6	118.7 (7)	H25B—C25—H25C	109.5
C10—C9—C6	116.4 (7)	C25—O1—H1A	109.5
C11—C10—C9	119.9 (7)	H2WA—O2W—H2WB	110.3
C11—C10—H10	120.1	H3WB—O3W—H3WA	111.5
C9—C10—H10	120.1	H5WA—O5W—H5WB	109.3
N2—Cu1—N1—C1	179.5 (6)	C4—C5—C6—C9	0.0 (8)
N4—Cu1—N1—C1	3.4 (6)	C5—C4—C7—C8	−1.5 (10)
N3—Cu1—N1—C1	89.1 (6)	C3—C4—C7—C8	178.6 (7)
Cl1—Cu1—N1—C1	−93.3 (6)	C4—C7—C8—C9	1.2 (11)
N2—Cu1—N1—C5	0.8 (4)	C7—C8—C9—C10	−179.6 (7)
N4—Cu1—N1—C5	−175.4 (4)	C7—C8—C9—C6	−0.2 (10)
N3—Cu1—N1—C5	−89.7 (4)	N2—C6—C9—C8	−179.7 (6)
Cl1—Cu1—N1—C5	87.9 (4)	C5—C6—C9—C8	−0.4 (9)
N4—Cu1—N2—C6	99 (4)	N2—C6—C9—C10	−0.2 (9)
N3—Cu1—N2—C6	123.6 (5)	C5—C6—C9—C10	179.1 (6)
N1—Cu1—N2—C6	−0.7 (4)	C8—C9—C10—C11	179.2 (7)
Cl1—Cu1—N2—C6	−115.9 (4)	C6—C9—C10—C11	−0.2 (10)
N4—Cu1—N2—C12	−82 (4)	C9—C10—C11—C12	0.1 (12)
N3—Cu1—N2—C12	−57.5 (6)	C6—N2—C12—C11	−0.9 (10)
N1—Cu1—N2—C12	178.3 (6)	Cu1—N2—C12—C11	−179.8 (6)
Cl1—Cu1—N2—C12	63.1 (6)	C10—C11—C12—N2	0.4 (12)
N2—Cu1—N3—C13	0.8 (6)	C17—N3—C13—C14	0.5 (10)
N4—Cu1—N3—C13	179.1 (7)	Cu1—N3—C13—C14	171.4 (5)
N1—Cu1—N3—C13	84.0 (7)	N3—C13—C14—C15	−0.5 (11)
Cl1—Cu1—N3—C13	−93.5 (6)	C13—C14—C15—C16	−0.7 (11)
N2—Cu1—N3—C17	172.2 (4)	C14—C15—C16—C17	1.8 (11)
N4—Cu1—N3—C17	−9.4 (4)	C14—C15—C16—C19	−179.1 (7)
N1—Cu1—N3—C17	−104.6 (4)	C13—N3—C17—C16	0.7 (9)
Cl1—Cu1—N3—C17	78.0 (4)	Cu1—N3—C17—C16	−172.1 (5)
N2—Cu1—N4—C24	−156 (3)	C13—N3—C17—C18	−179.8 (6)
N3—Cu1—N4—C24	179.6 (7)	Cu1—N3—C17—C18	7.5 (7)
N1—Cu1—N4—C24	−56.6 (6)	C15—C16—C17—N3	−1.8 (10)
Cl1—Cu1—N4—C24	59.3 (6)	C19—C16—C17—N3	179.1 (6)
N2—Cu1—N4—C18	35 (4)	C15—C16—C17—C18	178.6 (6)
N3—Cu1—N4—C18	10.3 (5)	C19—C16—C17—C18	−0.5 (9)
N1—Cu1—N4—C18	134.2 (5)	C24—N4—C18—C21	1.4 (10)
Cl1—Cu1—N4—C18	−110.0 (5)	Cu1—N4—C18—C21	171.6 (5)
C5—N1—C1—C2	−3.0 (9)	C24—N4—C18—C17	−179.4 (6)
Cu1—N1—C1—C2	178.3 (5)	Cu1—N4—C18—C17	−9.2 (7)
N1—C1—C2—C3	3.8 (11)	N3—C17—C18—N4	0.7 (9)
C1—C2—C3—C4	−2.6 (11)	C16—C17—C18—N4	−179.7 (6)
C2—C3—C4—C5	0.9 (9)	N3—C17—C18—C21	179.9 (6)
C2—C3—C4—C7	−179.3 (7)	C16—C17—C18—C21	−0.5 (10)
C1—N1—C5—C4	1.2 (9)	C15—C16—C19—C20	−178.5 (7)
Cu1—N1—C5—C4	−179.8 (5)	C17—C16—C19—C20	0.6 (10)
C1—N1—C5—C6	−179.7 (5)	C16—C19—C20—C21	0.4 (11)
Cu1—N1—C5—C6	−0.7 (6)	N4—C18—C21—C20	−179.4 (6)
C3—C4—C5—N1	−0.1 (9)	C17—C18—C21—C20	1.5 (10)
C7—C4—C5—N1	−180.0 (6)	N4—C18—C21—C22	−1.1 (10)
C3—C4—C5—C6	−179.2 (6)	C17—C18—C21—C22	179.8 (6)
C7—C4—C5—C6	0.9 (8)	C19—C20—C21—C18	−1.4 (11)
C12—N2—C6—C5	−178.5 (6)	C19—C20—C21—C22	−179.6 (7)
Cu1—N2—C6—C5	0.5 (7)	C18—C21—C22—C23	0.3 (11)
C12—N2—C6—C9	0.8 (9)	C20—C21—C22—C23	178.5 (7)
Cu1—N2—C6—C9	179.8 (5)	C21—C22—C23—C24	0.2 (12)
N1—C5—C6—N2	0.2 (8)	C18—N4—C24—C23	−0.9 (11)
C4—C5—C6—N2	179.3 (5)	Cu1—N4—C24—C23	−169.7 (6)
N1—C5—C6—C9	−179.1 (5)	C22—C23—C24—N4	0.1 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6W—H6WA···O5W^i	0.84	2.09	2.90 (2)	163
O5W—H5WB···O4W^ii	0.82	2.36	2.936 (12)	128
O4W—H4WA···O5W^iii	0.82	2.17	2.936 (12)	156
O3W—H3WA···Cl2^iii	0.81	2.13	2.847 (17)	148
O3W—H3WB···O3W^i	0.80	2.41	2.786 (17)	110
O2W—H2WA···Cl2^iv	0.85	2.75	3.40 (6)	134
O1W—H1WA···O2W^v	0.85	2.06	2.61 (6)	122

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