Aqua­(pyridine-κN)(N-salicylideneglycinato-κ3N,O,O′)copper(II)

Li, Y.-G.; Zhu, H.-L.; Chen, X.-Z.; Ng, S.W.

doi:10.1107/S1600536805033647

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Aqua(pyridine-κN)(N-salicylideneglycinato-κ³N,O,O′)copper(II)

Y.-G. Li, H.-L. Zhu, X.-Z. Chen and S. W. Ng

In both of the two independent molecules of the title compound, [Cu(C₉H₇NO₃)(C₅H₅N)(H₂O)], the copper atom is in a square-pyramidal coordination with the apical site occupied by water. The two molecules are related by a non-crystallographic center of inversion. Hydrogen bonds link symmetry-equivalent molecules into zigzag chains that run along the a axis of the orthorhombic unit cell.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805033647/cf6465sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805033647/cf6465Isup2.hkl Contains datablock I

CCDC reference: 289688

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.011 Å
R factor = 0.041
wR factor = 0.137
Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
            identifier.
            Deep
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.480
           From the CIF: _refine_ls_abs_structure_Flack_su    0.020
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero .......       0.48
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         11
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4
PLAT731_ALERT_1_C Bond    Calc     0.86(3), Rep   0.850(10) ......       3.00 su-Rat
              O1W  -H1W1    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.84(4), Rep   0.850(10) ......       4.00 su-Rat
              O1W  -H1W2    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(4), Rep   0.850(10) ......       4.00 su-Rat
              O2W  -H2W1    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(4), Rep   0.850(10) ......       4.00 su-Rat
              O2W  -H2W2    1.555   1.555
PLAT732_ALERT_1_C Angle   Calc      109(5), Rep      109(2) ......       2.50 su-Rat
              H2W1 -O2W  -H2W2    1.555   1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(3), Rep   0.850(10) ......       3.00 su-Rat
              O1W  -H1#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(4), Rep   0.850(10) ......       4.00 su-Rat
              O1W  -H2#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(4), Rep   0.850(10) ......       4.00 su-Rat
              O1W  -H2#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(4), Rep   0.850(10) ......       4.00 su-Rat
              O2W  -H4#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(4), Rep   0.850(10) ......       4.00 su-Rat
              O2W  -H4#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(4), Rep   0.850(10) ......       4.00 su-Rat
              O2W  -H3#     1.555   1.555

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           27.50
           From the CIF: _reflns_number_total               6066
           Count of symmetry unique reflns         3331
           Completeness (_total/calc)            182.11%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2735
           Fraction of Friedel pairs measured     0.821
           Are heavy atom types Z>Si present        yes

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

  12 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Aqua(pyridine-κN)(N-salicylideneglycinato-κ³N,O,O')copper(II) top

Crystal data top

[Cu(C₉H₇NO₃)(C₅H₅N)(H₂O)]	F(000) = 1384
M_r = 337.81	D_x = 1.584 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 4366 reflections
a = 9.6232 (5) Å	θ = 2.8–24.9°
b = 10.8138 (6) Å	µ = 1.56 mm⁻¹
c = 27.219 (2) Å	T = 295 K
V = 2832.4 (3) Å³	Prism, deep blue
Z = 8	0.30 × 0.20 × 0.08 mm

Data collection top

Bruker APEX area-detector diffractometer	6066 independent reflections
Radiation source: fine-focus sealed tube	4788 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
φ and ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
T_min = 0.660, T_max = 0.885	k = −13→12
16774 measured reflections	l = −30→35

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.137	w = 1/[σ²(F_o²) + (0.0839P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
6066 reflections	Δρ_max = 0.48 e Å⁻³
396 parameters	Δρ_min = −0.40 e Å⁻³
7 restraints	Absolute structure: Flack (1983), 3294 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.48 (2)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.96362 (6)	0.33174 (5)	0.50000 (2)	0.03827 (16)
Cu2	0.78831 (6)	0.16624 (5)	0.69831 (2)	0.03743 (16)
O1	1.1050 (5)	0.3177 (3)	0.4503 (2)	0.047 (1)
O2	0.8113 (4)	0.3606 (4)	0.5474 (2)	0.049 (1)
O3	0.7052 (6)	0.5056 (4)	0.5916 (3)	0.053 (2)
O4	0.6466 (4)	0.1788 (3)	0.7471 (2)	0.048 (1)
O5	0.9419 (4)	0.1388 (4)	0.6508 (2)	0.045 (1)
O6	1.0504 (6)	−0.0049 (4)	0.6079 (3)	0.053 (2)
O1w	1.1087 (4)	0.2638 (4)	0.5662 (2)	0.050 (1)
O2w	0.6441 (4)	0.2365 (4)	0.6323 (2)	0.050 (1)
N1	0.9832 (7)	0.5108 (4)	0.5031 (4)	0.042 (2)
N2	0.9008 (5)	0.1562 (4)	0.4884 (2)	0.038 (1)
N3	0.7749 (6)	−0.0121 (4)	0.6960 (4)	0.037 (1)
N4	0.8516 (5)	0.3414 (4)	0.7100 (2)	0.038 (1)
C1	1.0573 (6)	0.5775 (5)	0.4751 (2)	0.046 (1)
C2	1.1508 (6)	0.5333 (7)	0.4382 (2)	0.043 (1)
C3	1.2279 (9)	0.6205 (7)	0.4117 (3)	0.056 (2)
C4	1.3260 (9)	0.586 (1)	0.3781 (3)	0.071 (3)
C5	1.3443 (8)	0.464 (1)	0.3690 (3)	0.061 (2)
C6	1.2699 (8)	0.3740 (7)	0.3923 (3)	0.050 (2)
C7	1.1713 (6)	0.4054 (6)	0.4281 (2)	0.040 (1)
C8	0.8907 (6)	0.5682 (5)	0.5401 (2)	0.049 (1)
C9	0.7954 (6)	0.4741 (6)	0.5607 (3)	0.039 (1)
C10	0.9336 (7)	0.0942 (6)	0.4482 (3)	0.057 (2)
C11	0.887 (1)	−0.0236 (8)	0.4389 (4)	0.074 (3)
C12	0.8052 (7)	−0.0817 (7)	0.4733 (3)	0.066 (2)
C13	0.772 (1)	−0.0191 (7)	0.5152 (4)	0.059 (2)
C14	0.8205 (7)	0.0978 (5)	0.5211 (2)	0.056 (2)
C15	0.5794 (6)	0.0866 (6)	0.7699 (2)	0.040 (1)
C16	0.4810 (8)	0.1167 (7)	0.8055 (3)	0.050 (2)
C17	0.4067 (9)	0.0272 (9)	0.8304 (3)	0.062 (2)
C18	0.4318 (9)	−0.0973 (7)	0.8204 (3)	0.061 (2)
C19	0.5283 (8)	−0.1283 (7)	0.7862 (3)	0.053 (2)
C20	0.6011 (6)	−0.0373 (6)	0.7601 (2)	0.039 (1)
C21	0.7001 (5)	−0.0823 (5)	0.7232 (2)	0.041 (1)
C22	0.8619 (6)	−0.0682 (5)	0.6589 (2)	0.047 (1)
C23	0.9621 (6)	0.0275 (6)	0.6363 (3)	0.044 (2)
C24	0.8190 (7)	0.4023 (6)	0.7515 (3)	0.056 (2)
C25	0.870 (1)	0.5183 (7)	0.7612 (4)	0.064 (2)
C26	0.9474 (7)	0.5788 (6)	0.7270 (3)	0.062 (2)
C27	0.979 (1)	0.5189 (7)	0.6855 (5)	0.070 (3)
C28	0.9286 (7)	0.4000 (6)	0.6773 (2)	0.054 (2)
H1w1	1.120 (6)	0.333 (2)	0.581 (2)	0.04 (2)*
H1w2	1.108 (8)	0.206 (3)	0.587 (2)	0.07 (2)*
H2w1	0.635 (7)	0.169 (3)	0.617 (2)	0.05 (2)*
H2w2	0.661 (6)	0.294 (3)	0.612 (2)	0.05 (2)*
H1	1.0502	0.6627	0.4789	0.056*
H3	1.2119	0.7042	0.4171	0.067*
H4	1.3791	0.6451	0.3618	0.086*
H5	1.4104	0.4402	0.3459	0.074*
H6	1.2845	0.2913	0.3844	0.060*
H8a	0.9461	0.6040	0.5663	0.058*
H8b	0.8372	0.6340	0.5250	0.058*
H10	0.9907	0.1321	0.4251	0.069*
H11	0.9112	−0.0636	0.4099	0.089*
H12	0.7733	−0.1618	0.4680	0.080*
H13	0.7163	−0.0557	0.5392	0.071*
H14	0.7966	0.1399	0.5497	0.067*
H16	0.4649	0.1996	0.8127	0.060*
H17	0.3406	0.0498	0.8537	0.074*
H18	0.3828	−0.1586	0.8370	0.073*
H19	0.5465	−0.2113	0.7800	0.063*
H21	0.7093	−0.1674	0.7194	0.049*
H22a	0.8039	−0.1030	0.6333	0.056*
H22b	0.9151	−0.1350	0.6735	0.056*
H24	0.7603	0.3648	0.7742	0.067*
H25	0.8512	0.5556	0.7913	0.077*
H26	0.9777	0.6594	0.7324	0.074*
H27	1.0342	0.5570	0.6619	0.084*
H28	0.9500	0.3605	0.6479	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0397 (3)	0.0305 (3)	0.0447 (3)	−0.0010 (2)	0.0079 (3)	0.0044 (3)
Cu2	0.0381 (3)	0.0296 (3)	0.0445 (3)	−0.0010 (2)	0.0069 (2)	0.0026 (3)
O1	0.048 (2)	0.039 (2)	0.054 (3)	0.005 (2)	0.018 (2)	0.009 (2)
O2	0.051 (2)	0.037 (2)	0.058 (3)	0.004 (2)	0.014 (2)	0.006 (2)
O3	0.049 (4)	0.047 (3)	0.064 (5)	0.008 (2)	0.004 (3)	0.000 (2)
O4	0.050 (2)	0.036 (2)	0.057 (3)	0.000 (2)	0.013 (2)	0.008 (2)
O5	0.049 (2)	0.032 (2)	0.055 (3)	−0.002 (2)	0.017 (2)	0.001 (2)
O6	0.065 (5)	0.052 (3)	0.041 (4)	0.007 (2)	0.021 (3)	0.002 (2)
O1w	0.050 (2)	0.043 (2)	0.056 (2)	−0.005 (2)	0.004 (2)	0.009 (2)
O2w	0.050 (2)	0.044 (2)	0.057 (3)	−0.007 (2)	0.004 (2)	0.005 (2)
N1	0.045 (3)	0.036 (2)	0.045 (4)	−0.004 (2)	0.004 (3)	0.000 (2)
N2	0.038 (2)	0.038 (2)	0.038 (3)	−0.003 (2)	0.005 (2)	0.003 (2)
N3	0.036 (3)	0.030 (2)	0.044 (4)	0.000 (2)	0.000 (3)	0.008 (2)
N4	0.040 (2)	0.035 (2)	0.039 (2)	−0.003 (2)	0.004 (2)	0.002 (2)
C1	0.050 (3)	0.035 (3)	0.054 (3)	−0.006 (2)	−0.012 (3)	0.012 (2)
C2	0.035 (3)	0.054 (3)	0.040 (4)	−0.011 (3)	−0.003 (2)	0.016 (4)
C3	0.055 (5)	0.059 (4)	0.054 (5)	−0.024 (3)	−0.014 (3)	0.017 (3)
C4	0.058 (5)	0.106 (7)	0.050 (5)	−0.046 (5)	0.002 (4)	0.024 (5)
C5	0.048 (4)	0.097 (6)	0.039 (4)	−0.010 (5)	0.003 (3)	0.013 (5)
C6	0.050 (4)	0.065 (4)	0.033 (4)	−0.003 (3)	0.005 (3)	0.007 (3)
C7	0.034 (3)	0.047 (4)	0.041 (4)	−0.008 (3)	−0.006 (2)	0.008 (3)
C8	0.046 (3)	0.039 (3)	0.061 (4)	−0.003 (2)	0.013 (3)	−0.006 (3)
C9	0.036 (3)	0.046 (3)	0.034 (3)	0.014 (3)	−0.001 (2)	−0.002 (3)
C10	0.066 (4)	0.055 (4)	0.051 (4)	−0.012 (3)	0.020 (3)	−0.012 (3)
C11	0.092 (7)	0.060 (4)	0.070 (7)	−0.019 (5)	0.030 (6)	−0.029 (5)
C12	0.079 (5)	0.051 (4)	0.069 (5)	−0.028 (3)	0.009 (4)	−0.013 (3)
C13	0.076 (6)	0.055 (4)	0.048 (5)	−0.024 (4)	0.014 (4)	0.007 (4)
C14	0.088 (5)	0.037 (3)	0.042 (3)	−0.009 (3)	0.024 (3)	−0.004 (3)
C15	0.024 (3)	0.056 (4)	0.040 (4)	0.000 (3)	0.000 (2)	0.011 (3)
C16	0.049 (4)	0.058 (4)	0.042 (4)	−0.001 (3)	0.002 (3)	−0.001 (3)
C17	0.047 (4)	0.098 (6)	0.041 (4)	−0.027 (5)	0.006 (3)	−0.001 (5)
C18	0.071 (5)	0.062 (5)	0.050 (5)	−0.031 (4)	0.009 (4)	0.012 (4)
C19	0.065 (5)	0.049 (3)	0.044 (4)	−0.019 (3)	0.001 (3)	0.005 (3)
C20	0.037 (3)	0.042 (3)	0.039 (3)	−0.009 (3)	−0.003 (2)	0.004 (3)
C21	0.037 (3)	0.036 (2)	0.050 (3)	−0.004 (2)	−0.001 (2)	0.004 (2)
C22	0.047 (3)	0.035 (3)	0.057 (4)	0.000 (2)	0.003 (3)	−0.005 (3)
C23	0.038 (4)	0.041 (3)	0.052 (4)	−0.001 (3)	−0.001 (3)	0.017 (4)
C24	0.071 (4)	0.046 (4)	0.052 (4)	−0.016 (3)	0.011 (3)	−0.006 (3)
C25	0.072 (5)	0.064 (4)	0.057 (5)	−0.016 (4)	0.015 (4)	−0.023 (4)
C26	0.071 (5)	0.045 (4)	0.070 (5)	−0.020 (3)	0.008 (3)	−0.015 (3)
C27	0.085 (6)	0.044 (4)	0.082 (8)	−0.025 (4)	0.032 (5)	−0.006 (4)
C28	0.070 (4)	0.046 (4)	0.047 (4)	−0.014 (3)	0.010 (3)	−0.001 (3)

Geometric parameters (Å, º) top

Cu1—O1	1.924 (4)	C16—C17	1.382 (10)
Cu1—O2	1.977 (4)	C17—C18	1.395 (12)
Cu1—O1w	2.396 (4)	C18—C19	1.357 (11)
Cu1—N1	1.948 (4)	C19—C20	1.402 (9)
Cu1—N2	2.017 (4)	C20—C21	1.466 (8)
Cu2—O4	1.908 (4)	C22—C23	1.544 (9)
Cu2—O5	1.987 (4)	C24—C25	1.372 (9)
Cu2—O2w	2.393 (4)	C25—C26	1.360 (12)
Cu2—N3	1.934 (4)	C26—C27	1.338 (13)
Cu2—N4	2.015 (4)	C27—C28	1.392 (9)
O1—C7	1.293 (7)	O1w—H1w1	0.85 (1)
O2—C9	1.289 (8)	O1w—H1w2	0.85 (1)
O3—C9	1.255 (9)	O2w—H2w1	0.85 (1)
O4—C15	1.340 (7)	O2w—H2w2	0.85 (1)
O5—C23	1.281 (9)	C1—H1	0.93
O6—C23	1.200 (9)	C3—H3	0.93
N1—C1	1.27 (1)	C4—H4	0.93
N1—C8	1.48 (1)	C5—H5	0.93
N2—C10	1.324 (8)	C6—H6	0.93
N2—C14	1.336 (7)	C8—H8a	0.97
N3—C21	1.282 (9)	C8—H8b	0.97
N3—C22	1.45 (1)	C10—H10	0.93
N4—C28	1.321 (7)	C11—H11	0.93
N4—C24	1.343 (8)	C12—H12	0.93
C1—C2	1.43 (1)	C13—H13	0.93
C2—C3	1.400 (9)	C14—H14	0.93
C2—C7	1.424 (9)	C16—H16	0.93
C3—C4	1.37 (1)	C17—H17	0.93
C4—C5	1.36 (1)	C18—H18	0.93
C5—C6	1.36 (1)	C19—H19	0.93
C6—C7	1.402 (9)	C21—H21	0.93
C8—C9	1.480 (9)	C22—H22a	0.97
C10—C11	1.372 (9)	C22—H22b	0.97
C11—C12	1.38 (1)	C24—H24	0.93
C12—C13	1.37 (1)	C25—H25	0.93
C13—C14	1.359 (9)	C26—H26	0.93
C15—C20	1.382 (9)	C27—H27	0.93
C15—C16	1.393 (9)	C28—H28	0.93

O1—Cu1—O1w	95.3 (2)	N3—C21—C20	124.3 (6)
O1—Cu1—O2	174.3 (2)	N3—C22—C23	111.0 (5)
O1—Cu1—N2	91.6 (2)	O6—C23—O5	125.4 (6)
O1—Cu1—N1	92.3 (3)	O6—C23—C22	120.2 (6)
O2—Cu1—O1w	89.4 (2)	O5—C23—C22	114.4 (6)
O2—Cu1—N2	91.6 (2)	N4—C24—C25	121.8 (7)
O2—Cu1—N1	83.5 (3)	C26—C25—C24	120.3 (9)
O1w—Cu1—N1	102.5 (3)	C27—C26—C25	117.9 (7)
O1w—Cu1—N2	90.2 (2)	C26—C27—C28	120.3 (8)
N1—Cu1—N2	166.3 (3)	N4—C28—C27	121.9 (7)
O4—Cu2—O5	174.6 (2)	Cu1—O1w—H1w1	99 (4)
O4—Cu2—N3	92.6 (3)	Cu1—O1w—H1w2	137 (5)
O4—Cu2—N4	92.2 (2)	H1w1—O1w—H1w2	109 (2)
O4—Cu2—O2w	94.9 (2)	Cu2—O2w—H2w1	99 (4)
O5—Cu2—O2w	89.5 (2)	Cu2—O2w—H2w2	128 (4)
O5—Cu2—N3	83.1 (3)	H2w1—O2w—H2w2	109 (2)
O5—Cu2—N4	91.1 (2)	N1—C1—H1	117.1
O2w—Cu2—N3	104.7 (3)	C2—C1—H1	117.1
O2w—Cu2—N4	89.7 (2)	C4—C3—H3	119.1
N3—Cu2—N4	164.3 (2)	C2—C3—H3	119.1
C7—O1—Cu1	128.3 (4)	C5—C4—H4	120.7
C9—O2—Cu1	115.0 (4)	C3—C4—H4	120.7
C15—O4—Cu2	127.9 (4)	C4—C5—H5	118.6
C23—O5—Cu2	117.0 (4)	C6—C5—H5	118.6
C1—N1—C8	120.6 (5)	C5—C6—H6	119.8
C1—N1—Cu1	126.4 (6)	C7—C6—H6	119.8
C8—N1—Cu1	112.8 (5)	C9—C8—H8a	109.7
C10—N2—C14	116.7 (5)	N1—C8—H8a	109.7
C10—N2—Cu1	122.3 (4)	C9—C8—H8b	109.7
C14—N2—Cu1	121.0 (4)	N1—C8—H8b	109.7
C21—N3—C22	118.7 (4)	H8a—C8—H8b	108.2
C21—N3—Cu2	127.6 (6)	N2—C10—H10	118.5
C22—N3—Cu2	113.8 (5)	C11—C10—H10	118.5
C28—N4—C24	117.6 (5)	C10—C11—H11	120.5
C28—N4—Cu2	120.8 (4)	C12—C11—H11	120.5
C24—N4—Cu2	121.5 (4)	C13—C12—H12	120.7
N1—C1—C2	125.9 (6)	C11—C12—H12	120.7
C3—C2—C7	118.8 (7)	C14—C13—H13	120.7
C3—C2—C1	118.1 (7)	C12—C13—H13	120.7
C7—C2—C1	123.2 (6)	N2—C14—H14	117.9
C4—C3—C2	121.9 (8)	C13—C14—H14	117.9
C5—C4—C3	118.5 (7)	C17—C16—H16	119.0
C4—C5—C6	122.8 (8)	C15—C16—H16	119.0
C5—C6—C7	120.4 (7)	C16—C17—H17	120.3
O1—C7—C6	118.8 (6)	C18—C17—H17	120.3
O1—C7—C2	123.6 (6)	C19—C18—H18	120.3
C6—C7—C2	117.6 (6)	C17—C18—H18	120.3
C9—C8—N1	110.0 (5)	C18—C19—H19	119.4
O3—C9—O2	122.0 (6)	C20—C19—H19	119.4
O3—C9—C8	119.7 (6)	N3—C21—H21	117.9
O2—C9—C8	118.3 (6)	C20—C21—H21	117.9
N2—C10—C11	123.0 (7)	N3—C22—H22a	109.4
C10—C11—C12	119.1 (8)	C23—C22—H22a	109.4
C13—C12—C11	118.5 (6)	N3—C22—H22b	109.4
C14—C13—C12	118.5 (7)	C23—C22—H22b	109.4
N2—C14—C13	124.2 (6)	H22a—C22—H22b	108.0
O4—C15—C20	124.0 (6)	N4—C24—H24	119.1
O4—C15—C16	118.4 (6)	C25—C24—H24	119.1
C20—C15—C16	117.6 (6)	C26—C25—H25	119.9
C17—C16—C15	122.0 (7)	C24—C25—H25	119.9
C16—C17—C18	119.4 (8)	C27—C26—H26	121.0
C19—C18—C17	119.4 (7)	C25—C26—H26	121.0
C18—C19—C20	121.1 (7)	C26—C27—H27	119.8
C15—C20—C19	120.5 (6)	C28—C27—H27	119.8
C15—C20—C21	123.5 (6)	N4—C28—H28	119.0
C19—C20—C21	116.0 (6)	C27—C28—H28	119.0

N1—Cu1—O1—C7	−4.5 (6)	Cu1—O1—C7—C6	−179.2 (5)
N2—Cu1—O1—C7	162.4 (5)	Cu1—O1—C7—C2	1.3 (9)
O1w—Cu1—O1—C7	−107.3 (5)	C5—C6—C7—O1	−178.3 (7)
N1—Cu1—O2—C9	−2.9 (5)	C5—C6—C7—C2	1 (1)
N2—Cu1—O2—C9	−170.1 (5)	C3—C2—C7—O1	−179.7 (6)
O1w—Cu1—O2—C9	99.7 (4)	C1—C2—C7—O1	1.9 (9)
N3—Cu2—O4—C15	3.6 (6)	C3—C2—C7—C6	0.8 (9)
N4—Cu2—O4—C15	−161.4 (5)	C1—C2—C7—C6	−177.6 (6)
O2w—Cu2—O4—C15	108.6 (5)	C1—N1—C8—C9	168.4 (7)
N3—Cu2—O5—C23	4.6 (5)	Cu1—N1—C8—C9	−6.9 (8)
N4—Cu2—O5—C23	170.0 (5)	Cu1—O2—C9—O3	−178.2 (6)
O2w—Cu2—O5—C23	−100.3 (5)	Cu1—O2—C9—C8	−0.4 (8)
O1—Cu1—N1—C1	6.6 (8)	N1—C8—C9—O3	−177.4 (7)
O2—Cu1—N1—C1	−169.5 (8)	N1—C8—C9—O2	4.8 (9)
N2—Cu1—N1—C1	−100 (1)	C14—N2—C10—C11	1 (1)
O1w—Cu1—N1—C1	102.5 (7)	Cu1—N2—C10—C11	−177.5 (7)
O1—Cu1—N1—C8	−178.5 (6)	N2—C10—C11—C12	−1 (2)
O2—Cu1—N1—C8	5.5 (6)	C10—C11—C12—C13	1 (2)
N2—Cu1—N1—C8	75 (2)	C11—C12—C13—C14	0 (1)
O1w—Cu1—N1—C8	−82.5 (6)	C10—N2—C14—C13	0 (1)
O1—Cu1—N2—C10	−17.4 (5)	Cu1—N2—C14—C13	178.3 (6)
N1—Cu1—N2—C10	89 (2)	C12—C13—C14—N2	0 (1)
O2—Cu1—N2—C10	157.8 (5)	Cu2—O4—C15—C20	−1.9 (8)
O1w—Cu1—N2—C10	−112.7 (5)	Cu2—O4—C15—C16	178.5 (5)
O1—Cu1—N2—C14	164.1 (5)	O4—C15—C16—C17	179.6 (7)
N1—Cu1—N2—C14	−89 (1)	C20—C15—C16—C17	0 (1)
O2—Cu1—N2—C14	−20.6 (5)	C15—C16—C17—C18	1 (1)
O1w—Cu1—N2—C14	68.8 (5)	C16—C17—C18—C19	0 (1)
O4—Cu2—N3—C21	−4.9 (7)	C17—C18—C19—C20	−1 (1)
O5—Cu2—N3—C21	171.8 (8)	O4—C15—C20—C19	178.8 (6)
N4—Cu2—N3—C21	103.0 (9)	C16—C15—C20—C19	−1.5 (9)
O2w—Cu2—N3—C21	−100.6 (7)	O4—C15—C20—C21	−0.4 (9)
O4—Cu2—N3—C22	175.5 (5)	C16—C15—C20—C21	179.3 (6)
O5—Cu2—N3—C22	−7.8 (5)	C18—C19—C20—C15	2 (1)
N4—Cu2—N3—C22	−77 (2)	C18—C19—C20—C21	−178.5 (7)
O2w—Cu2—N3—C22	79.8 (5)	C22—N3—C21—C20	−176.1 (6)
O4—Cu2—N4—C28	−162.2 (5)	Cu2—N3—C21—C20	4 (1)
N3—Cu2—N4—C28	89.9 (13)	C15—C20—C21—N3	−1 (1)
O5—Cu2—N4—C28	22.1 (5)	C19—C20—C21—N3	179.8 (7)
O2w—Cu2—N4—C28	−67.3 (5)	C21—N3—C22—C23	−170.1 (6)
O4—Cu2—N4—C24	18.7 (5)	Cu2—N3—C22—C23	9.5 (8)
N3—Cu2—N4—C24	−89 (1)	Cu2—O5—C23—O6	−179.7 (7)
O5—Cu2—N4—C24	−156.9 (5)	Cu2—O5—C23—C22	−0.3 (7)
O2w—Cu2—N4—C24	113.6 (5)	N3—C22—C23—O6	173.5 (8)
C8—N1—C1—C2	179.7 (6)	N3—C22—C23—O5	−6.0 (9)
Cu1—N1—C1—C2	−6 (1)	C28—N4—C24—C25	−4 (1)
N1—C1—C2—C3	−177.9 (7)	Cu2—N4—C24—C25	175.3 (7)
N1—C1—C2—C7	1 (1)	N4—C24—C25—C26	5 (1)
C7—C2—C3—C4	−3 (1)	C24—C25—C26—C27	−4 (1)
C1—C2—C3—C4	175.7 (7)	C25—C26—C27—C28	2 (2)
C2—C3—C4—C5	3 (1)	C24—N4—C28—C27	2 (1)
C3—C4—C5—C6	−1 (1)	Cu2—N4—C28—C27	−177.1 (7)
C4—C5—C6—C7	−1 (1)	C26—C27—C28—N4	−1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w1···O3ⁱ	0.85 (1)	1.95 (3)	2.749 (6)	155 (5)
O1w—H1w2···O5	0.85 (1)	2.46 (5)	3.114 (6)	134 (6)
O1w—H1w2···O6	0.85 (1)	2.41 (3)	3.169 (6)	149 (5)
O2w—H2w2···O2	0.85 (1)	2.39 (3)	3.121 (6)	145 (5)
O2w—H2w2···O3	0.85 (1)	2.39 (2)	3.169 (7)	153 (4)
O2w—H2w1···O6ⁱⁱ	0.85 (1)	1.97 (3)	2.744 (6)	151 (5)

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

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