catena-Poly­[[[di­chloro­copper(II)]-μ-1,3,5-tris(2-pyridyl­oxy­methyl)­benzene] methanol solvate]

In the title compound, {[CuCl₂(tpomb)]·CH₃OH}_n [where tpomb = 1,3,5-tris(2-pyridyl­oxy­methyl)­benzene, C₂₄H₂₁N₃O₃], two pyridyl­oxy­methyl pendant arms of the tpomb ligand bridge Cu^II centres via Cu—N bonds to form one-dimensional coordination polymer chains.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.028
• wR factor = 0.075
• Data-to-parameter ratio = 19.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT731_ALERT_1_C Bond    Calc     0.79(2), Rep    0.793(9) ......       2.22 su-Rat
              O1M  -H1M     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.79(2), Rep    0.793(9) ......       2.22 su-Rat
              O1M  -H1M     1.555   1.555

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

   2 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and XPREP (Siemens, 1995); program(s) used to solve structure: SIR97 (Altomare et al. 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and WinGX32 (Farrugia, 1999); software used to prepare material for publication: enCIFer (Version 1.0; Allen at al., 2004).

catena-Poly[[[dichlorocopper(II)]-µ-1,3,5-tris(2-pyridyloxymethyl)benzene] methanol solvate]

Crystal data

[CuCl2(C24H21N3O3)]·CH4O	F(000) = 2328
Mr = 565.92	Dx = 1.510 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 16661 reflections
a = 12.7397 (8) Å	θ = 2.2–28.2°
b = 15.6191 (10) Å	µ = 1.13 mm^−1
c = 25.0173 (15) Å	T = 150 K
V = 4978.0 (5) Å^3	Plate, pale-green
Z = 8	0.35 × 0.34 × 0.15 mm

Data collection

Siemens SMART 1000 CCD diffractometer	6076 independent reflections
Radiation source: fine-focus sealed tube	5070 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω scans	θmax = 28.4°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	h = −16→17
Tmin = 0.717, Tmax = 0.844	k = −20→20
46409 measured reflections	l = −33→33

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0401P)^2 + 2.1134P] where P = (Fo^2 + 2Fc^2)/3
6076 reflections	(Δ/σ)max = 0.003
320 parameters	Δρmax = 0.39 e Å^−3
2 restraints	Δρmin = −0.25 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	0.258106 (14)	0.246556 (11)	0.888115 (7)	0.01744 (6)
Cl1	0.12214 (3)	0.23207 (2)	0.946571 (16)	0.02559 (9)
Cl2	0.41284 (3)	0.17983 (2)	0.881891 (16)	0.02369 (9)
N1	0.31159 (10)	0.35134 (8)	0.92320 (5)	0.0189 (2)
N2	0.13333 (11)	0.58478 (10)	0.62402 (6)	0.0275 (3)
N3	−0.31121 (9)	0.19506 (8)	0.67544 (5)	0.0178 (2)
O1	0.20341 (9)	0.40468 (7)	0.86257 (4)	0.0226 (2)
O2	0.21694 (10)	0.45370 (8)	0.63090 (5)	0.0320 (3)
O3	−0.19873 (9)	0.27730 (7)	0.72054 (4)	0.0226 (2)
C1	0.09479 (12)	0.43670 (9)	0.78885 (6)	0.0213 (3)
C2	0.13373 (12)	0.44433 (9)	0.73707 (6)	0.0216 (3)
H2	0.1968	0.4751	0.7308	0.026*
C3	0.08046 (12)	0.40698 (9)	0.69456 (6)	0.0208 (3)
C4	−0.01071 (12)	0.36012 (10)	0.70435 (6)	0.0217 (3)
H4	−0.0465	0.3335	0.6754	0.026*
C5	−0.04974 (12)	0.35195 (9)	0.75585 (6)	0.0207 (3)
C6	0.00265 (12)	0.39152 (10)	0.79810 (6)	0.0218 (3)
H6	−0.0248	0.3876	0.8333	0.026*
C7	0.15194 (13)	0.47514 (10)	0.83562 (6)	0.0240 (3)
H7A	0.2043	0.5176	0.8232	0.029*
H7B	0.1020	0.5040	0.8600	0.029*
C8	0.26378 (11)	0.42215 (9)	0.90547 (6)	0.0182 (3)
C9	0.27648 (13)	0.50153 (9)	0.92970 (6)	0.0220 (3)
H9	0.2407	0.5508	0.9170	0.026*
C10	0.34357 (13)	0.50577 (10)	0.97320 (6)	0.0244 (3)
H10	0.3542	0.5588	0.9910	0.029*
C11	0.39517 (12)	0.43303 (10)	0.99084 (6)	0.0237 (3)
H11	0.4422	0.4358	1.0202	0.028*
C12	0.37699 (12)	0.35674 (10)	0.96502 (6)	0.0215 (3)
H12	0.4117	0.3065	0.9772	0.026*
C13	0.11640 (14)	0.41382 (12)	0.63708 (7)	0.0296 (4)
H13A	0.1194	0.3556	0.6214	0.035*
H13B	0.0637	0.4471	0.6167	0.035*
C14	0.21925 (13)	0.53869 (11)	0.61827 (6)	0.0260 (3)
C15	0.31503 (13)	0.57044 (12)	0.59954 (7)	0.0296 (4)
H15	0.3755	0.5350	0.5976	0.036*
C16	0.31850 (14)	0.65475 (13)	0.58406 (7)	0.0341 (4)
H16	0.3816	0.6785	0.5702	0.041*
C17	0.22878 (14)	0.70507 (12)	0.58879 (7)	0.0338 (4)
H17	0.2293	0.7635	0.5783	0.041*
C18	0.13935 (14)	0.66797 (12)	0.60902 (7)	0.0300 (4)
H18	0.0784	0.7026	0.6127	0.036*
C19	−0.14401 (12)	0.29807 (10)	0.76901 (6)	0.0232 (3)
H19A	−0.1215	0.2449	0.7872	0.028*
H19B	−0.1912	0.3299	0.7934	0.028*
C20	−0.27689 (11)	0.21950 (10)	0.72358 (6)	0.0193 (3)
C21	−0.31981 (13)	0.18844 (11)	0.77089 (6)	0.0254 (3)
H21	−0.2933	0.2062	0.8046	0.030*
C22	−0.40191 (13)	0.13107 (11)	0.76751 (7)	0.0294 (4)
H22	−0.4335	0.1093	0.7991	0.035*
C23	−0.43812 (13)	0.10525 (11)	0.71784 (7)	0.0284 (4)
H23	−0.4941	0.0653	0.7149	0.034*
C24	−0.39131 (12)	0.13861 (10)	0.67289 (6)	0.0225 (3)
H24	−0.4163	0.1213	0.6388	0.027*
C1M	−0.0728 (2)	0.39986 (15)	0.98157 (9)	0.0540 (6)
H2M	−0.0230	0.3973	1.0114	0.081*
H3M	−0.1179	0.3491	0.9823	0.081*
H4M	−0.1161	0.4514	0.9849	0.081*
O1M	−0.01724 (15)	0.40236 (12)	0.93297 (6)	0.0640 (5)
H1M	0.0232 (18)	0.3645 (13)	0.9286 (9)	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.01679 (10)	0.01611 (10)	0.01941 (10)	−0.00153 (6)	−0.00134 (7)	−0.00226 (6)
Cl1	0.02476 (19)	0.02565 (19)	0.02637 (19)	−0.00255 (14)	0.00583 (15)	−0.00279 (15)
Cl2	0.01938 (17)	0.02088 (17)	0.0308 (2)	0.00215 (13)	−0.00099 (14)	−0.00026 (14)
N1	0.0192 (6)	0.0172 (6)	0.0203 (6)	−0.0017 (5)	−0.0018 (5)	−0.0005 (5)
N2	0.0215 (7)	0.0372 (8)	0.0239 (7)	−0.0010 (6)	0.0012 (5)	−0.0022 (6)
N3	0.0159 (6)	0.0180 (6)	0.0196 (6)	−0.0006 (5)	0.0005 (5)	0.0011 (5)
O1	0.0274 (6)	0.0158 (5)	0.0246 (6)	0.0015 (4)	−0.0106 (5)	−0.0018 (4)
O2	0.0257 (6)	0.0346 (7)	0.0357 (7)	−0.0012 (5)	0.0072 (5)	0.0025 (5)
O3	0.0230 (5)	0.0254 (5)	0.0196 (5)	−0.0097 (4)	−0.0020 (4)	0.0019 (4)
C1	0.0224 (7)	0.0150 (6)	0.0264 (8)	0.0018 (6)	−0.0087 (6)	0.0010 (6)
C2	0.0183 (7)	0.0176 (7)	0.0289 (8)	−0.0008 (6)	−0.0038 (6)	0.0024 (6)
C3	0.0204 (7)	0.0178 (7)	0.0241 (8)	0.0021 (6)	−0.0001 (6)	0.0001 (6)
C4	0.0218 (7)	0.0208 (7)	0.0225 (7)	−0.0008 (6)	−0.0046 (6)	−0.0024 (6)
C5	0.0203 (7)	0.0189 (7)	0.0229 (7)	−0.0001 (6)	−0.0030 (6)	0.0004 (6)
C6	0.0242 (7)	0.0205 (7)	0.0205 (7)	0.0003 (6)	−0.0041 (6)	0.0004 (6)
C7	0.0277 (8)	0.0163 (7)	0.0280 (8)	−0.0001 (6)	−0.0105 (7)	0.0014 (6)
C8	0.0183 (7)	0.0184 (7)	0.0180 (7)	−0.0018 (5)	−0.0011 (6)	−0.0003 (5)
C9	0.0246 (8)	0.0175 (7)	0.0239 (8)	−0.0017 (6)	−0.0024 (6)	−0.0006 (6)
C10	0.0266 (8)	0.0227 (8)	0.0239 (8)	−0.0063 (6)	−0.0008 (6)	−0.0049 (6)
C11	0.0236 (7)	0.0286 (8)	0.0190 (7)	−0.0077 (6)	−0.0037 (6)	0.0004 (6)
C12	0.0206 (7)	0.0224 (7)	0.0213 (7)	−0.0025 (6)	−0.0034 (6)	0.0033 (6)
C13	0.0289 (9)	0.0324 (9)	0.0274 (9)	−0.0082 (7)	0.0036 (7)	−0.0019 (7)
C14	0.0246 (8)	0.0337 (9)	0.0198 (7)	−0.0030 (7)	0.0007 (6)	−0.0018 (6)
C15	0.0198 (8)	0.0438 (10)	0.0252 (8)	−0.0019 (7)	0.0017 (6)	−0.0020 (7)
C16	0.0257 (8)	0.0502 (11)	0.0265 (9)	−0.0116 (8)	−0.0006 (7)	0.0022 (8)
C17	0.0357 (9)	0.0349 (10)	0.0308 (9)	−0.0081 (8)	−0.0091 (8)	0.0022 (7)
C18	0.0275 (8)	0.0359 (9)	0.0265 (8)	0.0011 (7)	−0.0046 (7)	−0.0032 (7)
C19	0.0228 (7)	0.0280 (8)	0.0186 (7)	−0.0050 (6)	−0.0030 (6)	−0.0002 (6)
C20	0.0165 (7)	0.0195 (7)	0.0218 (7)	−0.0013 (6)	−0.0011 (6)	0.0014 (6)
C21	0.0240 (8)	0.0326 (8)	0.0197 (7)	−0.0055 (6)	0.0008 (6)	0.0028 (6)
C22	0.0261 (8)	0.0367 (9)	0.0254 (8)	−0.0072 (7)	0.0039 (7)	0.0075 (7)
C23	0.0236 (8)	0.0305 (8)	0.0312 (9)	−0.0108 (7)	0.0002 (7)	0.0039 (7)
C24	0.0201 (7)	0.0222 (7)	0.0251 (8)	−0.0039 (6)	−0.0015 (6)	0.0001 (6)
C1M	0.0719 (16)	0.0500 (13)	0.0400 (12)	0.0121 (11)	0.0145 (11)	0.0072 (10)
O1M	0.0809 (13)	0.0729 (12)	0.0380 (8)	0.0446 (10)	0.0207 (8)	0.0176 (8)

Geometric parameters (Å, º)

Cu1—N1	1.9782 (12)	C8—C9	1.390 (2)
Cu1—N3^i	1.9888 (12)	C9—C10	1.385 (2)
Cu1—Cl2	2.2352 (4)	C9—H9	0.9500
Cu1—Cl1	2.2782 (4)	C10—C11	1.385 (2)
Cu1—O1	2.6445 (11)	C10—H10	0.9500
Cu1—O3^i	2.8146 (11)	C11—C12	1.375 (2)
N1—C8	1.3383 (19)	C11—H11	0.9500
N1—C12	1.3401 (19)	C12—H12	0.9500
N2—C14	1.318 (2)	C13—H13A	0.9900
N2—C18	1.355 (2)	C13—H13B	0.9900
N3—C20	1.3367 (19)	C14—C15	1.398 (2)
N3—C24	1.3501 (19)	C15—C16	1.373 (3)
N3—Cu1^ii	1.9888 (12)	C15—H15	0.9500
O1—C8	1.3481 (18)	C16—C17	1.392 (3)
O1—C7	1.4477 (18)	C16—H16	0.9500
O2—C14	1.365 (2)	C17—C18	1.375 (3)
O2—C13	1.433 (2)	C17—H17	0.9500
O3—C20	1.3463 (19)	C18—H18	0.9500
O3—C19	1.4359 (18)	C19—H19A	0.9900
C1—C6	1.389 (2)	C19—H19B	0.9900
C1—C2	1.392 (2)	C20—C21	1.391 (2)
C1—C7	1.503 (2)	C21—C22	1.380 (2)
C2—C3	1.390 (2)	C21—H21	0.9500
C2—H2	0.9500	C22—C23	1.385 (2)
C3—C4	1.395 (2)	C22—H22	0.9500
C3—C13	1.513 (2)	C23—C24	1.375 (2)
C4—C5	1.387 (2)	C23—H23	0.9500
C4—H4	0.9500	C24—H24	0.9500
C5—C6	1.395 (2)	C1M—O1M	1.407 (3)
C5—C19	1.503 (2)	C1M—H2M	0.9800
C6—H6	0.9500	C1M—H3M	0.9800
C7—H7A	0.9900	C1M—H4M	0.9800
C7—H7B	0.9900	O1M—H1M	0.793 (9)
N1—Cu1—N3^i	147.39 (5)	C11—C10—H10	119.9
N1—Cu1—Cl2	96.48 (4)	C9—C10—H10	119.9
N3^i—Cu1—Cl2	98.47 (4)	C12—C11—C10	118.76 (14)
N1—Cu1—Cl1	93.40 (4)	C12—C11—H11	120.6
N3^i—Cu1—Cl1	97.78 (4)	C10—C11—H11	120.6
Cl2—Cu1—Cl1	131.983 (17)	N1—C12—C11	121.74 (14)
N1—Cu1—O1	54.92 (4)	N1—C12—H12	119.1
N3^i—Cu1—O1	93.87 (4)	C11—C12—H12	119.1
Cl2—Cu1—O1	130.62 (3)	O2—C13—C3	113.81 (14)
Cl1—Cu1—O1	92.73 (3)	O2—C13—H13A	108.8
N1—Cu1—O3^i	102.71 (4)	C3—C13—H13A	108.8
N3^i—Cu1—O3^i	51.95 (4)	O2—C13—H13B	108.8
Cl2—Cu1—O3^i	80.79 (3)	C3—C13—H13B	108.8
Cl1—Cu1—O3^i	141.76 (3)	H13A—C13—H13B	107.7
O1—Cu1—O3^i	70.05 (3)	N2—C14—O2	119.21 (15)
C8—N1—C12	119.32 (13)	N2—C14—C15	124.59 (17)
C8—N1—Cu1	112.33 (10)	O2—C14—C15	116.20 (15)
C12—N1—Cu1	127.78 (10)	C16—C15—C14	117.57 (16)
C14—N2—C18	116.53 (15)	C16—C15—H15	121.2
C20—N3—C24	118.44 (13)	C14—C15—H15	121.2
C20—N3—Cu1^ii	117.36 (10)	C15—C16—C17	119.40 (16)
C24—N3—Cu1^ii	124.19 (10)	C15—C16—H16	120.3
C8—O1—C7	118.38 (11)	C17—C16—H16	120.3
C8—O1—Cu1	81.17 (8)	C18—C17—C16	118.27 (18)
C7—O1—Cu1	160.36 (9)	C18—C17—H17	120.9
C14—O2—C13	117.85 (13)	C16—C17—H17	120.9
C20—O3—C19	117.58 (11)	N2—C18—C17	123.59 (17)
C6—C1—C2	119.98 (14)	N2—C18—H18	118.2
C6—C1—C7	118.85 (14)	C17—C18—H18	118.2
C2—C1—C7	121.16 (14)	O3—C19—C5	109.23 (12)
C3—C2—C1	120.14 (14)	O3—C19—H19A	109.8
C3—C2—H2	119.9	C5—C19—H19A	109.8
C1—C2—H2	119.9	O3—C19—H19B	109.8
C2—C3—C4	119.51 (14)	C5—C19—H19B	109.8
C2—C3—C13	123.36 (14)	H19A—C19—H19B	108.3
C4—C3—C13	117.13 (14)	N3—C20—O3	112.49 (13)
C5—C4—C3	120.66 (14)	N3—C20—C21	122.57 (14)
C5—C4—H4	119.7	O3—C20—C21	124.93 (14)
C3—C4—H4	119.7	C22—C21—C20	118.17 (15)
C4—C5—C6	119.46 (14)	C22—C21—H21	120.9
C4—C5—C19	122.79 (13)	C20—C21—H21	120.9
C6—C5—C19	117.68 (14)	C21—C22—C23	119.76 (15)
C1—C6—C5	120.21 (15)	C21—C22—H22	120.1
C1—C6—H6	119.9	C23—C22—H22	120.1
C5—C6—H6	119.9	C24—C23—C22	118.60 (15)
O1—C7—C1	106.16 (12)	C24—C23—H23	120.7
O1—C7—H7A	110.5	C22—C23—H23	120.7
C1—C7—H7A	110.5	N3—C24—C23	122.45 (15)
O1—C7—H7B	110.5	N3—C24—H24	118.8
C1—C7—H7B	110.5	C23—C24—H24	118.8
H7A—C7—H7B	108.7	O1M—C1M—H2M	109.5
N1—C8—O1	110.87 (12)	O1M—C1M—H3M	109.5
N1—C8—C9	122.67 (14)	H2M—C1M—H3M	109.5
O1—C8—C9	126.46 (13)	O1M—C1M—H4M	109.5
C10—C9—C8	117.20 (14)	H2M—C1M—H4M	109.5
C10—C9—H9	121.4	H3M—C1M—H4M	109.5
C8—C9—H9	121.4	C1M—O1M—H1M	115.2 (16)
C11—C10—C9	120.27 (14)
N3^i—Cu1—N1—C8	24.73 (16)	C7—O1—C8—N1	−175.40 (13)
Cl2—Cu1—N1—C8	141.64 (10)	Cu1—O1—C8—N1	6.65 (11)
Cl1—Cu1—N1—C8	−85.42 (10)	C7—O1—C8—C9	5.1 (2)
O1—Cu1—N1—C8	5.52 (9)	Cu1—O1—C8—C9	−172.82 (16)
O3^i—Cu1—N1—C8	59.66 (11)	N1—C8—C9—C10	1.4 (2)
N3^i—Cu1—N1—C12	−164.11 (12)	O1—C8—C9—C10	−179.21 (15)
Cl2—Cu1—N1—C12	−47.19 (13)	C8—C9—C10—C11	0.2 (2)
Cl1—Cu1—N1—C12	85.74 (13)	C9—C10—C11—C12	−1.2 (2)
O1—Cu1—N1—C12	176.69 (15)	C8—N1—C12—C11	1.0 (2)
O3^i—Cu1—N1—C12	−129.17 (13)	Cu1—N1—C12—C11	−169.60 (12)
N1—Cu1—O1—C8	−5.13 (8)	C10—C11—C12—N1	0.5 (2)
N3^i—Cu1—O1—C8	−174.89 (9)	C14—O2—C13—C3	−97.58 (17)
Cl2—Cu1—O1—C8	−70.26 (9)	C2—C3—C13—O2	7.0 (2)
Cl1—Cu1—O1—C8	87.11 (8)	C4—C3—C13—O2	−172.73 (14)
O3^i—Cu1—O1—C8	−127.88 (9)	C18—N2—C14—O2	−177.68 (14)
N1—Cu1—O1—C7	−179.8 (3)	C18—N2—C14—C15	2.0 (2)
N3^i—Cu1—O1—C7	10.5 (3)	C13—O2—C14—N2	15.2 (2)
Cl2—Cu1—O1—C7	115.1 (3)	C13—O2—C14—C15	−164.50 (15)
Cl1—Cu1—O1—C7	−87.5 (3)	N2—C14—C15—C16	−2.7 (3)
O3^i—Cu1—O1—C7	57.5 (3)	O2—C14—C15—C16	176.93 (15)
C6—C1—C2—C3	0.1 (2)	C14—C15—C16—C17	1.6 (3)
C7—C1—C2—C3	178.89 (13)	C15—C16—C17—C18	0.0 (3)
C1—C2—C3—C4	−1.6 (2)	C14—N2—C18—C17	−0.1 (2)
C1—C2—C3—C13	178.75 (15)	C16—C17—C18—N2	−0.8 (3)
C2—C3—C4—C5	1.3 (2)	C20—O3—C19—C5	170.90 (13)
C13—C3—C4—C5	−178.99 (14)	C4—C5—C19—O3	−14.6 (2)
C3—C4—C5—C6	0.4 (2)	C6—C5—C19—O3	168.60 (13)
C3—C4—C5—C19	−176.37 (14)	C24—N3—C20—O3	−178.50 (13)
C2—C1—C6—C5	1.6 (2)	Cu1^ii—N3—C20—O3	0.34 (17)
C7—C1—C6—C5	−177.21 (13)	C24—N3—C20—C21	0.6 (2)
C4—C5—C6—C1	−1.8 (2)	Cu1^ii—N3—C20—C21	179.47 (12)
C19—C5—C6—C1	175.10 (14)	C19—O3—C20—N3	−170.19 (12)
C8—O1—C7—C1	177.81 (13)	C19—O3—C20—C21	10.7 (2)
Cu1—O1—C7—C1	−8.2 (4)	N3—C20—C21—C22	−0.9 (2)
C6—C1—C7—O1	75.17 (17)	O3—C20—C21—C22	178.13 (16)
C2—C1—C7—O1	−103.60 (16)	C20—C21—C22—C23	0.9 (3)
C12—N1—C8—O1	178.49 (13)	C21—C22—C23—C24	−0.6 (3)
Cu1—N1—C8—O1	−9.51 (15)	C20—N3—C24—C23	−0.4 (2)
C12—N1—C8—C9	−2.0 (2)	Cu1^ii—N3—C24—C23	−179.13 (12)
Cu1—N1—C8—C9	169.97 (12)	C22—C23—C24—N3	0.4 (3)

Symmetry codes: (i) x+1/2, y, −z+3/2; (ii) x−1/2, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1M—H1M···Cl1	0.79 (1)	2.46 (1)	3.2161 (16)	159 (2)