Aqua­bis(2-phenyl-1,3,7,8-tetra­azacyclo­penta­[l]phenanthrene)copper(II) dihydrate

In the title compound, [Cu(C₁₉H₁₁N₄)₂(H₂O)]·2H₂O or [Cu(L)₂(H₂O)]·2H₂O, where HL is 2-phenyl-1H-1,3,7,8,-tetra­azacyclo­penta­[l]phenanthrene, the Cu^II atom is five-coord­inated by four N atoms from two L⁻ ligands and one O atom from one water mol­ecule. A three-dimensional supra­molecular structure is formed through π–π and hydrogen-bonding inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.069
• wR factor = 0.152
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       O2W    -   HW22   ...          ?

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.113
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.11
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.18
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.79 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   O1W     ..       9.81 su
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          6
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

aquabis(2-phenyl-1,3,7,8-tetraazacyclopenta[l]phenanthrene)copper(II) dihydrate

Crystal data

[Cu(C19H11N4)2(H2O)]·2H2O	F(000) = 1460
Mr = 708.22	Dx = 1.471 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p2ybc	Cell parameters from total reflections
a = 9.2897 (19) Å	θ = 3.0–27.5°
b = 11.466 (2) Å	µ = 0.74 mm^−1
c = 30.189 (6) Å	T = 292 K
β = 95.85 (3)°	Block, blue
V = 3198.9 (11) Å^3	0.33 × 0.26 × 0.18 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	7231 independent reflections
Radiation source: rotor target	3942 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.113
Detector resolution: 10.0 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
ω scans	h = −12→12
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −14→12
Tmin = 0.777, Tmax = 0.875	l = −39→39
29006 measured reflections

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0471P)^2 + 3.7579P] where P = (Fo^2 + 2Fc^2)/3
7231 reflections	(Δ/σ)max = 0.001
475 parameters	Δρmax = 0.96 e Å^−3
2 restraints	Δρmin = −0.44 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
C1	0.7248 (5)	0.8971 (4)	0.69241 (16)	0.0491 (12)
H1	0.6328	0.8656	0.6861	0.059*
C2	0.8093 (6)	0.8568 (4)	0.72909 (18)	0.0596 (14)
H2	0.7737	0.8004	0.7472	0.072*
C3	0.9475 (5)	0.9001 (4)	0.73900 (17)	0.0508 (12)
H3	1.0060	0.8725	0.7636	0.061*
C4	0.9985 (4)	0.9863 (4)	0.71150 (14)	0.0367 (10)
C5	0.9036 (4)	1.0232 (3)	0.67469 (13)	0.0330 (9)
C6	0.9444 (4)	1.1141 (3)	0.64585 (13)	0.0308 (9)
C7	1.0821 (4)	1.1668 (3)	0.65205 (13)	0.0300 (9)
C8	1.1119 (4)	1.2565 (4)	0.62286 (14)	0.0361 (10)
H8	1.2013	1.2938	0.6262	0.043*
C9	1.0104 (5)	1.2888 (4)	0.58969 (15)	0.0423 (11)
H9	1.0297	1.3482	0.5701	0.051*
C10	0.8771 (5)	1.2327 (4)	0.58514 (15)	0.0423 (11)
H10	0.8078	1.2561	0.5625	0.051*
C11	1.1783 (4)	1.1253 (3)	0.68828 (13)	0.0316 (9)
C12	1.1385 (4)	1.0396 (4)	0.71764 (14)	0.0356 (10)
C13	1.3551 (4)	1.0924 (4)	0.73696 (13)	0.0344 (10)
C14	1.5004 (4)	1.0992 (4)	0.76121 (14)	0.0378 (10)
C15	1.5988 (5)	1.1813 (5)	0.74913 (17)	0.0583 (14)
H15	1.5710	1.2344	0.7266	0.070*
C16	1.7371 (6)	1.1849 (6)	0.7701 (2)	0.0729 (17)
H16	1.8031	1.2383	0.7608	0.087*
C17	1.7785 (6)	1.1105 (5)	0.8045 (2)	0.0698 (16)
H17	1.8721	1.1134	0.8187	0.084*
C18	1.6821 (6)	1.0327 (5)	0.8177 (2)	0.0702 (17)
H18	1.7091	0.9839	0.8417	0.084*
C19	1.5447 (5)	1.0246 (5)	0.79622 (18)	0.0600 (14)
H19	1.4810	0.9689	0.8052	0.072*
C20	0.7850 (5)	0.9992 (4)	0.52006 (16)	0.0467 (12)
H20	0.8524	1.0585	0.5263	0.056*
C21	0.7940 (5)	0.9326 (5)	0.48241 (16)	0.0538 (13)
H21	0.8649	0.9483	0.4636	0.065*
C22	0.6984 (5)	0.8436 (4)	0.47296 (15)	0.0458 (11)
H22	0.7053	0.7968	0.4481	0.055*
C23	0.5893 (4)	0.8232 (4)	0.50106 (14)	0.0349 (9)
C24	0.5869 (4)	0.8966 (3)	0.53835 (14)	0.0327 (9)
C25	0.4797 (4)	0.8820 (4)	0.56909 (14)	0.0351 (10)
C26	0.3891 (5)	0.9466 (4)	0.63305 (16)	0.0527 (13)
H26	0.3921	0.9991	0.6566	0.063*
C27	0.2835 (5)	0.8606 (4)	0.62987 (18)	0.0575 (14)
H27	0.2176	0.8558	0.6510	0.069*
C28	0.2770 (5)	0.7834 (4)	0.59558 (17)	0.0516 (13)
H28	0.2080	0.7243	0.5936	0.062*
C29	0.3753 (4)	0.7931 (4)	0.56301 (14)	0.0374 (10)
C30	0.3792 (4)	0.7202 (3)	0.52528 (14)	0.0351 (10)
C31	0.4815 (4)	0.7346 (4)	0.49543 (14)	0.0354 (10)
C32	0.3483 (5)	0.5896 (4)	0.47534 (15)	0.0397 (10)
C33	0.2857 (5)	0.4883 (4)	0.45006 (16)	0.0445 (11)
C34	0.3454 (6)	0.4476 (5)	0.41263 (18)	0.0602 (14)
H34	0.4277	0.4830	0.4037	0.072*
C35	0.2827 (8)	0.3543 (5)	0.3885 (2)	0.0824 (19)
H35	0.3224	0.3287	0.3632	0.099*
C36	0.1631 (7)	0.2995 (5)	0.4016 (2)	0.083 (2)
H36	0.1221	0.2366	0.3855	0.100*
C37	0.1047 (7)	0.3389 (5)	0.4388 (2)	0.0773 (18)
H37	0.0235	0.3019	0.4478	0.093*
C38	0.1641 (5)	0.4323 (4)	0.46305 (18)	0.0576 (13)
H38	0.1227	0.4578	0.4881	0.069*
N1	0.8451 (4)	1.1468 (3)	0.61198 (11)	0.0347 (8)
N2	0.7675 (4)	0.9791 (3)	0.66526 (12)	0.0379 (8)
N3	0.6842 (4)	0.9830 (3)	0.54798 (12)	0.0386 (9)
N4	0.4866 (4)	0.9573 (3)	0.60373 (12)	0.0404 (9)
N5	1.2512 (4)	1.0181 (3)	0.74866 (12)	0.0391 (9)
N6	1.3182 (3)	1.1586 (3)	0.70067 (11)	0.0317 (8)
N7	0.2930 (4)	0.6268 (3)	0.51256 (12)	0.0402 (9)
N8	0.4619 (4)	0.6514 (3)	0.46291 (12)	0.0393 (9)
O1W	0.5551 (4)	1.2090 (3)	0.62895 (13)	0.0636 (10)
O2W	1.2242 (4)	0.8751 (4)	0.82334 (14)	0.0642 (11)
O3W	0.7077 (5)	0.5618 (4)	0.42491 (13)	0.0658 (11)
Cu1	0.65735 (5)	1.06285 (5)	0.608656 (18)	0.03804 (17)
HW11	0.473 (4)	1.202 (6)	0.6443 (19)	0.11 (2)*
HW12	0.624 (4)	1.255 (4)	0.6459 (16)	0.081 (19)*
HW21	1.239 (7)	0.922 (6)	0.803 (2)	0.10 (2)*
HW22	1.158 (5)	0.923 (4)	0.8393 (15)	0.051 (14)*
HW31	0.627 (7)	0.594 (6)	0.437 (2)	0.11 (2)*
HW32	0.748 (8)	0.505 (7)	0.439 (3)	0.13 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.049 (3)	0.045 (3)	0.053 (3)	−0.013 (2)	0.005 (2)	0.010 (2)
C2	0.063 (3)	0.055 (3)	0.060 (4)	−0.016 (3)	0.003 (3)	0.020 (3)
C3	0.049 (3)	0.054 (3)	0.049 (3)	−0.001 (2)	0.003 (2)	0.018 (2)
C4	0.043 (2)	0.033 (2)	0.034 (2)	−0.0005 (19)	0.004 (2)	0.0033 (19)
C5	0.039 (2)	0.028 (2)	0.032 (2)	−0.0034 (18)	0.0062 (19)	−0.0026 (18)
C6	0.035 (2)	0.028 (2)	0.029 (2)	0.0025 (18)	0.0031 (18)	0.0018 (17)
C7	0.032 (2)	0.031 (2)	0.027 (2)	−0.0011 (18)	0.0054 (17)	−0.0018 (17)
C8	0.035 (2)	0.035 (2)	0.039 (3)	−0.0063 (19)	0.0049 (19)	0.0060 (19)
C9	0.046 (3)	0.038 (3)	0.042 (3)	−0.003 (2)	0.002 (2)	0.011 (2)
C10	0.043 (2)	0.041 (3)	0.042 (3)	0.002 (2)	−0.003 (2)	0.014 (2)
C11	0.032 (2)	0.032 (2)	0.030 (2)	0.0005 (18)	0.0035 (18)	−0.0009 (18)
C12	0.036 (2)	0.039 (2)	0.032 (2)	−0.0011 (19)	0.0045 (19)	0.0044 (19)
C13	0.037 (2)	0.038 (2)	0.028 (2)	0.0025 (19)	0.0028 (18)	−0.0042 (18)
C14	0.038 (2)	0.040 (3)	0.034 (2)	0.004 (2)	−0.0020 (19)	−0.0035 (19)
C15	0.051 (3)	0.070 (4)	0.050 (3)	−0.015 (3)	−0.014 (2)	0.015 (3)
C16	0.056 (3)	0.091 (5)	0.066 (4)	−0.021 (3)	−0.016 (3)	0.019 (3)
C17	0.042 (3)	0.080 (4)	0.083 (5)	0.001 (3)	−0.014 (3)	−0.004 (3)
C18	0.058 (3)	0.080 (4)	0.067 (4)	0.017 (3)	−0.020 (3)	0.013 (3)
C19	0.049 (3)	0.059 (3)	0.069 (4)	0.003 (3)	−0.005 (3)	0.020 (3)
C20	0.040 (2)	0.052 (3)	0.050 (3)	−0.014 (2)	0.008 (2)	−0.008 (2)
C21	0.048 (3)	0.067 (3)	0.049 (3)	−0.010 (3)	0.016 (2)	−0.009 (3)
C22	0.047 (3)	0.053 (3)	0.037 (3)	−0.004 (2)	0.005 (2)	−0.007 (2)
C23	0.033 (2)	0.035 (2)	0.035 (2)	0.0029 (19)	−0.0017 (19)	0.0003 (19)
C24	0.031 (2)	0.029 (2)	0.037 (2)	0.0006 (18)	−0.0013 (18)	−0.0006 (18)
C25	0.034 (2)	0.033 (2)	0.037 (2)	0.0011 (19)	0.0025 (19)	−0.0042 (19)
C26	0.051 (3)	0.059 (3)	0.052 (3)	−0.005 (3)	0.021 (2)	−0.021 (3)
C27	0.052 (3)	0.062 (3)	0.062 (3)	−0.019 (3)	0.026 (3)	−0.019 (3)
C28	0.051 (3)	0.051 (3)	0.056 (3)	−0.016 (2)	0.015 (2)	−0.011 (3)
C29	0.035 (2)	0.037 (2)	0.039 (3)	0.0011 (19)	0.000 (2)	−0.001 (2)
C30	0.041 (2)	0.029 (2)	0.035 (2)	−0.0007 (19)	0.000 (2)	0.0013 (19)
C31	0.038 (2)	0.032 (2)	0.034 (2)	0.0021 (19)	−0.0046 (19)	−0.0037 (19)
C32	0.043 (2)	0.030 (2)	0.043 (3)	0.003 (2)	−0.011 (2)	−0.002 (2)
C33	0.056 (3)	0.027 (2)	0.047 (3)	0.002 (2)	−0.016 (2)	−0.003 (2)
C34	0.070 (3)	0.052 (3)	0.056 (3)	−0.006 (3)	−0.003 (3)	−0.011 (3)
C35	0.105 (5)	0.066 (4)	0.072 (4)	−0.001 (4)	−0.010 (4)	−0.036 (3)
C36	0.092 (5)	0.051 (4)	0.098 (5)	−0.012 (3)	−0.030 (4)	−0.020 (4)
C37	0.072 (4)	0.059 (4)	0.095 (5)	−0.016 (3)	−0.018 (4)	−0.009 (4)
C38	0.059 (3)	0.046 (3)	0.064 (3)	−0.007 (3)	−0.011 (3)	−0.006 (3)
N1	0.0372 (18)	0.0311 (19)	0.035 (2)	0.0008 (16)	0.0005 (16)	0.0039 (16)
N2	0.0371 (19)	0.035 (2)	0.041 (2)	−0.0099 (16)	0.0039 (17)	0.0001 (16)
N3	0.0347 (19)	0.040 (2)	0.040 (2)	−0.0035 (16)	−0.0013 (17)	−0.0030 (17)
N4	0.0368 (19)	0.042 (2)	0.043 (2)	0.0002 (16)	0.0043 (17)	−0.0114 (18)
N5	0.0382 (19)	0.042 (2)	0.036 (2)	0.0015 (17)	0.0024 (17)	0.0079 (17)
N6	0.0351 (18)	0.0328 (19)	0.0269 (18)	0.0021 (15)	0.0010 (15)	−0.0008 (15)
N7	0.046 (2)	0.033 (2)	0.041 (2)	−0.0031 (17)	−0.0016 (18)	−0.0015 (17)
N8	0.041 (2)	0.037 (2)	0.038 (2)	−0.0003 (17)	−0.0043 (17)	−0.0051 (17)
O1W	0.058 (2)	0.067 (3)	0.066 (3)	−0.008 (2)	0.008 (2)	−0.010 (2)
O2W	0.071 (3)	0.064 (3)	0.057 (3)	0.007 (2)	0.005 (2)	0.026 (2)
O3W	0.084 (3)	0.055 (2)	0.063 (3)	−0.012 (2)	0.028 (2)	0.006 (2)
Cu1	0.0344 (3)	0.0368 (3)	0.0428 (3)	−0.0057 (2)	0.0035 (2)	−0.0054 (3)

Geometric parameters (Å, º)

C1—N2	1.334 (5)	C22—H22	0.9300
C1—C2	1.371 (7)	C23—C24	1.407 (6)
C1—H1	0.9300	C23—C31	1.425 (6)
C2—C3	1.380 (7)	C24—N3	1.353 (5)
C2—H2	0.9300	C24—C25	1.439 (5)
C3—C4	1.404 (6)	C25—N4	1.352 (5)
C3—H3	0.9300	C25—C29	1.406 (6)
C4—C5	1.411 (6)	C26—N4	1.335 (5)
C4—C12	1.432 (6)	C26—C27	1.388 (6)
C5—N2	1.364 (5)	C26—H26	0.9300
C5—C6	1.434 (5)	C27—C28	1.359 (6)
C6—N1	1.358 (5)	C27—H27	0.9300
C6—C7	1.410 (5)	C28—C29	1.413 (6)
C7—C8	1.400 (5)	C28—H28	0.9300
C7—C11	1.422 (5)	C29—C30	1.416 (6)
C8—C9	1.356 (6)	C30—N7	1.368 (5)
C8—H8	0.9300	C30—C31	1.385 (5)
C9—C10	1.390 (6)	C31—N8	1.367 (5)
C9—H9	0.9300	C32—N7	1.352 (5)
C10—N1	1.328 (5)	C32—N8	1.356 (5)
C10—H10	0.9300	C32—C33	1.476 (6)
C11—N6	1.369 (5)	C33—C34	1.389 (7)
C11—C12	1.398 (5)	C33—C38	1.391 (6)
C12—N5	1.354 (5)	C34—C35	1.388 (7)
C13—N6	1.348 (5)	C34—H34	0.9300
C13—N5	1.361 (5)	C35—C36	1.368 (8)
C13—C14	1.471 (6)	C35—H35	0.9300
C14—C15	1.386 (6)	C36—C37	1.373 (8)
C14—C19	1.389 (6)	C36—H36	0.9300
C15—C16	1.374 (7)	C37—C38	1.381 (7)
C15—H15	0.9300	C37—H37	0.9300
C16—C17	1.369 (8)	C38—H38	0.9300
C16—H16	0.9300	N1—Cu1	1.986 (3)
C17—C18	1.353 (8)	N2—Cu1	2.129 (4)
C17—H17	0.9300	N3—Cu1	2.086 (4)
C18—C19	1.375 (7)	N4—Cu1	1.989 (3)
C18—H18	0.9300	O1W—Cu1	2.051 (4)
C19—H19	0.9300	O1W—HW11	0.94 (2)
C20—N3	1.335 (5)	O1W—HW12	0.94 (2)
C20—C21	1.379 (6)	O2W—HW21	0.84 (7)
C20—H20	0.9300	O2W—HW22	0.99 (5)
C21—C22	1.364 (6)	O3W—HW31	0.94 (7)
C21—H21	0.9300	O3W—HW32	0.85 (8)
C22—C23	1.406 (6)
N2—C1—C2	123.5 (4)	N4—C25—C24	116.3 (4)
N2—C1—H1	118.2	C29—C25—C24	120.9 (4)
C2—C1—H1	118.2	N4—C26—C27	122.8 (4)
C1—C2—C3	119.8 (5)	N4—C26—H26	118.6
C1—C2—H2	120.1	C27—C26—H26	118.6
C3—C2—H2	120.1	C28—C27—C26	119.5 (4)
C2—C3—C4	119.2 (5)	C28—C27—H27	120.3
C2—C3—H3	120.4	C26—C27—H27	120.3
C4—C3—H3	120.4	C27—C28—C29	119.8 (4)
C3—C4—C5	117.1 (4)	C27—C28—H28	120.1
C3—C4—C12	125.5 (4)	C29—C28—H28	120.1
C5—C4—C12	117.4 (4)	C25—C29—C28	116.9 (4)
N2—C5—C4	123.0 (4)	C25—C29—C30	117.3 (4)
N2—C5—C6	116.1 (4)	C28—C29—C30	125.8 (4)
C4—C5—C6	120.9 (4)	N7—C30—C31	109.3 (4)
N1—C6—C7	121.2 (4)	N7—C30—C29	128.7 (4)
N1—C6—C5	117.2 (4)	C31—C30—C29	121.9 (4)
C7—C6—C5	121.6 (4)	N8—C31—C30	109.5 (4)
C8—C7—C6	117.8 (4)	N8—C31—C23	128.6 (4)
C8—C7—C11	125.5 (4)	C30—C31—C23	121.9 (4)
C6—C7—C11	116.7 (3)	N7—C32—N8	116.0 (4)
C9—C8—C7	119.9 (4)	N7—C32—C33	121.0 (4)
C9—C8—H8	120.0	N8—C32—C33	123.0 (4)
C7—C8—H8	120.0	C34—C33—C38	118.5 (4)
C8—C9—C10	119.5 (4)	C34—C33—C32	121.1 (4)
C8—C9—H9	120.3	C38—C33—C32	120.4 (4)
C10—C9—H9	120.3	C35—C34—C33	120.3 (5)
N1—C10—C9	122.4 (4)	C35—C34—H34	119.8
N1—C10—H10	118.8	C33—C34—H34	119.8
C9—C10—H10	118.8	C36—C35—C34	120.8 (6)
N6—C11—C12	109.1 (4)	C36—C35—H35	119.6
N6—C11—C7	128.4 (4)	C34—C35—H35	119.6
C12—C11—C7	122.4 (4)	C35—C36—C37	119.0 (6)
N5—C12—C11	109.3 (3)	C35—C36—H36	120.5
N5—C12—C4	129.8 (4)	C37—C36—H36	120.5
C11—C12—C4	120.9 (4)	C36—C37—C38	121.3 (6)
N6—C13—N5	115.8 (4)	C36—C37—H37	119.4
N6—C13—C14	121.3 (4)	C38—C37—H37	119.4
N5—C13—C14	122.9 (4)	C37—C38—C33	120.1 (5)
C15—C14—C19	117.8 (4)	C37—C38—H38	120.0
C15—C14—C13	120.1 (4)	C33—C38—H38	120.0
C19—C14—C13	122.1 (4)	C10—N1—C6	119.2 (4)
C16—C15—C14	120.7 (5)	C10—N1—Cu1	125.4 (3)
C16—C15—H15	119.7	C6—N1—Cu1	115.4 (3)
C14—C15—H15	119.7	C1—N2—C5	117.4 (4)
C17—C16—C15	120.6 (5)	C1—N2—Cu1	131.5 (3)
C17—C16—H16	119.7	C5—N2—Cu1	111.1 (3)
C15—C16—H16	119.7	C20—N3—C24	117.6 (4)
C18—C17—C16	119.4 (5)	C20—N3—Cu1	130.3 (3)
C18—C17—H17	120.3	C24—N3—Cu1	111.9 (3)
C16—C17—H17	120.3	C26—N4—C25	118.2 (4)
C17—C18—C19	121.1 (5)	C26—N4—Cu1	126.6 (3)
C17—C18—H18	119.5	C25—N4—Cu1	114.9 (3)
C19—C18—H18	119.5	C12—N5—C13	103.0 (3)
C18—C19—C14	120.5 (5)	C13—N6—C11	102.8 (3)
C18—C19—H19	119.8	C32—N7—C30	102.6 (3)
C14—C19—H19	119.8	C32—N8—C31	102.5 (3)
N3—C20—C21	123.3 (4)	Cu1—O1W—HW11	120 (4)
N3—C20—H20	118.4	Cu1—O1W—HW12	108 (3)
C21—C20—H20	118.4	HW11—O1W—HW12	109 (5)
C22—C21—C20	119.6 (4)	HW21—O2W—HW22	99 (5)
C22—C21—H21	120.2	HW31—O3W—HW32	116 (6)
C20—C21—H21	120.2	N1—Cu1—N4	171.32 (14)
C21—C22—C23	119.5 (4)	N1—Cu1—O1W	91.15 (15)
C21—C22—H22	120.2	N4—Cu1—O1W	97.45 (15)
C23—C22—H22	120.2	N1—Cu1—N3	94.25 (14)
C22—C23—C24	117.0 (4)	N4—Cu1—N3	80.38 (14)
C22—C23—C31	126.0 (4)	O1W—Cu1—N3	136.21 (15)
C24—C23—C31	117.0 (4)	N1—Cu1—N2	80.23 (13)
N3—C24—C23	123.0 (4)	N4—Cu1—N2	95.73 (14)
N3—C24—C25	116.0 (4)	O1W—Cu1—N2	109.16 (15)
C23—C24—C25	121.0 (4)	N3—Cu1—N2	114.58 (14)
N4—C25—C29	122.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—HW11···N6^i	0.94 (2)	2.39 (3)	3.292 (5)	162 (6)
O1W—HW12···O2W^ii	0.94 (2)	2.12 (2)	3.050 (5)	172 (5)
O2W—HW21···N5	0.84 (7)	1.98 (7)	2.819 (5)	171 (7)
O3W—HW31···N8	0.94 (7)	1.91 (7)	2.849 (6)	177 (6)
O3W—HW32···N7^iii	0.85 (8)	2.16 (7)	2.871 (5)	141 (7)

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