(Dimethyl­dithio­carbamato-κ²S,S′)­iodido(1,10-phenanthroline-κ²N,N′)copper(II)

In the title complex, [Cu(C₃H₆NS₂)I(C₁₂H₈N₂)], each Cu^II atom is coordinated by one iodide ion, two N atoms from a phenanthroline ligand and two S atoms from a dimethyl­dithio­carbamate ligand in a distorted square-pyramidal environment. There are two molecules in the asymmetric unit.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.050
• wR factor = 0.144
• Data-to-parameter ratio = 20.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  I1     -   Cu1     ..      26.13 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  I2     -   Cu2     ..      20.17 su

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.77
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   S2      ..       5.22 su
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C3
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C17
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C18
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C15 H14 Cu I N3 S2

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.770
            Tmax scaled      0.770 Tmin scaled      0.421
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1         (2)       2.06
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu2         (2)       2.07

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   5 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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S1. Comment

Research into transition metal complexes has been rapidly expanding because of their fascinating structural diversity, as well as their potential applications as functional materials and enzymes (Noro et al., 2000; Yaghi et al., 1998). Dialkyldithiocarbamates anions, which are typical sulfur ligands, acting as monodentate, bidentate or bridging ligands, are often chosen for the preparation of a considerable structural variety of complexes (Engelhardt et al., 1998; Fernández et al., 2000; Koh, et al., 2003). We report here the crystal structure of the title copper(II) complex, (I), contanining a dimethyldithiocarbamate ligand.

The molecular structure of (I) is shown in Fig. 1. In (1), there are two crystallographically independent Cu^II atoms in the asymmetric unit. Both are five-coordinated in a distorted square-pyramidal environment by one I atom in the apical position, two N atoms from a phenanthroline ligand and two S atoms from a dimethyldithiocarbamate ligand in the basal plane (Table 1).

Related literature

For related literature, see: Engelhardt et al. (1998); Fernández et al. (2000); Koh et al. (2003); Noro et al. (2000); Yaghi et al. (1998).

S2. Experimental

A mixture of Cu(Ac)₂.H₂O (0.16 g, 0.8 mmol), NaS₂CNMe₂.2H₂O (0.09 g, 0.4 mmol), 1,10-phenanthroline (0.08 g 0.4 mmol) and NaI.2H₂O (0.07 g, 0.4 mmol) was stirred in DMF (15 ml). 2-PrOH was diffused into the resulting solution, yielding single crystals of (I).

S3. Refinement

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (aromatic) or 0.96 Å (methyl), U_iso(H) = 1.2U_eq(C) (aromatic) or 1.5U_eq(C) (methyl).

Computing details

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures

Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids.

(Dimethyldithiocarbamato-κ²S,S')iodido(1,10-phenanthroline- κ²N,N')copper(II)

Crystal data

[Cu(C3H6NS2)I(C12H8N2)]	F(000) = 1912
Mr = 490.85	Dx = 1.871 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8049 reflections
a = 14.2931 (13) Å	θ = 3.1–27.5°
b = 17.4948 (13) Å	µ = 3.26 mm^−1
c = 14.6359 (16) Å	T = 293 K
β = 107.790 (4)°	Prism, black
V = 3484.8 (6) Å^3	0.30 × 0.20 × 0.08 mm
Z = 8

Data collection

Rigaku Mercury CCD diffractometer	7942 independent reflections
Radiation source: Sealed Tube	6762 reflections with I > 2σ(I)
Graphite Monochromator monochromator	Rint = 0.034
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	h = −18→18
Tmin = 0.547, Tmax = 1.000	k = −22→21
25019 measured reflections	l = −17→18

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.144	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0836P)^2 + 1.0573P] where P = (Fo^2 + 2Fc^2)/3
7942 reflections	(Δ/σ)max = 0.002
397 parameters	Δρmax = 0.82 e Å^−3
0 restraints	Δρmin = −0.60 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	0.54618 (5)	0.55197 (3)	0.86587 (5)	0.04700 (17)
Cu2	1.00225 (5)	0.61593 (4)	1.33013 (5)	0.04827 (17)
S1	0.42686 (10)	0.63047 (8)	0.89036 (11)	0.0543 (3)
S2	0.62636 (10)	0.66705 (8)	0.90659 (12)	0.0591 (4)
S3	0.93575 (10)	0.73224 (8)	1.35167 (11)	0.0558 (3)
S4	1.13164 (10)	0.69918 (8)	1.34873 (12)	0.0579 (4)
I1	0.51765 (3)	0.54788 (2)	0.65876 (2)	0.05071 (12)
I2	0.90939 (2)	0.60430 (2)	1.12905 (2)	0.05199 (12)
N1	0.5001 (3)	0.7725 (2)	0.9289 (3)	0.0521 (10)
N2	0.4799 (3)	0.4479 (2)	0.8607 (3)	0.0465 (10)
N3	0.6662 (3)	0.4841 (2)	0.8832 (3)	0.0416 (9)
N4	1.0712 (3)	0.8404 (3)	1.3710 (3)	0.0510 (10)
N5	0.9043 (3)	0.5482 (2)	1.3688 (3)	0.0473 (10)
N6	1.0793 (3)	0.5152 (2)	1.3508 (3)	0.0469 (9)
C1	0.5151 (4)	0.7001 (3)	0.9117 (3)	0.0472 (11)
C2	0.4034 (5)	0.7993 (4)	0.9317 (5)	0.0711 (17)
H2A	0.3583	0.7571	0.9198	0.107*
H2B	0.3791	0.8377	0.8834	0.107*
H2C	0.4096	0.8207	0.9937	0.107*
C3	0.5778 (5)	0.8294 (3)	0.9439 (5)	0.0749 (18)
H3A	0.6370	0.8052	0.9405	0.112*
H3B	0.5895	0.8525	1.0058	0.112*
H3C	0.5583	0.8680	0.8951	0.112*
C4	0.3883 (4)	0.4299 (4)	0.8548 (4)	0.0570 (13)
H4A	0.3467	0.4686	0.8623	0.068*
C5	0.3513 (4)	0.3560 (4)	0.8379 (5)	0.0671 (16)
H5A	0.2869	0.3457	0.8359	0.081*
C6	0.4106 (4)	0.2989 (4)	0.8242 (4)	0.0610 (14)
H6A	0.3860	0.2497	0.8099	0.073*
C7	0.5091 (4)	0.3148 (3)	0.8317 (3)	0.0462 (11)
C8	0.5770 (4)	0.2601 (3)	0.8185 (4)	0.0554 (13)
H8A	0.5562	0.2099	0.8038	0.066*
C9	0.6703 (4)	0.2786 (3)	0.8267 (4)	0.0535 (13)
H9A	0.7125	0.2412	0.8169	0.064*
C10	0.7056 (3)	0.3541 (3)	0.8500 (3)	0.0418 (10)
C11	0.8032 (4)	0.3790 (3)	0.8621 (4)	0.0535 (13)
H11A	0.8498	0.3448	0.8537	0.064*
C12	0.8281 (4)	0.4522 (3)	0.8859 (4)	0.0541 (13)
H12A	0.8926	0.4681	0.8961	0.065*
C13	0.7583 (4)	0.5039 (3)	0.8952 (4)	0.0493 (12)
H13A	0.7770	0.5544	0.9104	0.059*
C14	0.6403 (3)	0.4106 (3)	0.8620 (3)	0.0403 (10)
C15	0.5401 (3)	0.3899 (3)	0.8508 (3)	0.0399 (10)
C16	1.0494 (4)	0.7674 (3)	1.3596 (4)	0.0472 (11)
C17	0.9991 (4)	0.8958 (3)	1.3836 (5)	0.0611 (15)
H17A	0.9393	0.8697	1.3812	0.092*
H17B	0.9861	0.9332	1.3332	0.092*
H17C	1.0248	0.9207	1.4446	0.092*
C18	1.1674 (5)	0.8703 (4)	1.3727 (4)	0.0644 (15)
H18A	1.2080	0.8291	1.3636	0.097*
H18B	1.1981	0.8944	1.4334	0.097*
H18C	1.1592	0.9070	1.3221	0.097*
C19	0.8178 (4)	0.5667 (3)	1.3776 (4)	0.0552 (13)
H19A	0.7989	0.6177	1.3718	0.066*
C20	0.7540 (4)	0.5129 (4)	1.3954 (4)	0.0632 (15)
H20A	0.6930	0.5276	1.3997	0.076*
C21	0.7825 (4)	0.4377 (4)	1.4065 (4)	0.0639 (15)
H21A	0.7407	0.4012	1.4189	0.077*
C22	0.8737 (4)	0.4156 (3)	1.3991 (4)	0.0526 (12)
C23	0.9109 (5)	0.3398 (3)	1.4089 (4)	0.0621 (15)
H23A	0.8731	0.3008	1.4230	0.075*
C24	0.9981 (5)	0.3224 (3)	1.3988 (4)	0.0632 (15)
H24A	1.0189	0.2718	1.4045	0.076*
C25	1.0607 (4)	0.3806 (3)	1.3791 (4)	0.0545 (13)
C26	1.1541 (5)	0.3669 (4)	1.3700 (4)	0.0632 (15)
H26A	1.1796	0.3176	1.3762	0.076*
C27	1.2073 (4)	0.4269 (4)	1.3520 (5)	0.0658 (16)
H27A	1.2692	0.4188	1.3452	0.079*
C28	1.1676 (4)	0.5006 (4)	1.3439 (4)	0.0566 (13)
H28A	1.2050	0.5411	1.3331	0.068*
C29	1.0272 (4)	0.4564 (3)	1.3691 (3)	0.0428 (10)
C30	0.9323 (4)	0.4743 (3)	1.3794 (3)	0.0445 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0428 (3)	0.0411 (3)	0.0588 (4)	0.0056 (3)	0.0181 (3)	0.0003 (2)
Cu2	0.0419 (3)	0.0429 (3)	0.0619 (4)	0.0020 (3)	0.0187 (3)	−0.0001 (3)
S1	0.0478 (7)	0.0519 (8)	0.0675 (9)	0.0064 (6)	0.0240 (7)	−0.0016 (6)
S2	0.0477 (7)	0.0509 (8)	0.0796 (10)	0.0029 (6)	0.0205 (7)	−0.0107 (7)
S3	0.0461 (7)	0.0467 (7)	0.0772 (10)	0.0027 (6)	0.0227 (7)	−0.0037 (6)
S4	0.0466 (7)	0.0477 (8)	0.0833 (10)	−0.0005 (6)	0.0256 (7)	−0.0080 (6)
I1	0.0524 (2)	0.0530 (2)	0.0486 (2)	−0.00187 (15)	0.01823 (16)	0.00498 (13)
I2	0.0470 (2)	0.0554 (2)	0.0538 (2)	0.00504 (15)	0.01572 (16)	−0.00251 (14)
N1	0.057 (3)	0.048 (2)	0.050 (2)	0.009 (2)	0.015 (2)	−0.0111 (18)
N2	0.040 (2)	0.054 (3)	0.047 (2)	0.0056 (18)	0.0154 (18)	0.0077 (17)
N3	0.037 (2)	0.041 (2)	0.046 (2)	0.0029 (17)	0.0121 (17)	0.0036 (16)
N4	0.054 (3)	0.046 (2)	0.054 (3)	0.000 (2)	0.018 (2)	−0.0049 (18)
N5	0.040 (2)	0.051 (2)	0.051 (2)	0.0074 (18)	0.0141 (18)	0.0005 (18)
N6	0.042 (2)	0.047 (2)	0.051 (2)	0.0045 (19)	0.0133 (19)	−0.0004 (18)
C1	0.048 (3)	0.051 (3)	0.042 (3)	0.009 (2)	0.012 (2)	−0.003 (2)
C2	0.070 (4)	0.071 (4)	0.073 (4)	0.022 (3)	0.024 (3)	−0.017 (3)
C3	0.081 (4)	0.051 (4)	0.087 (5)	−0.003 (3)	0.016 (4)	−0.017 (3)
C4	0.047 (3)	0.064 (4)	0.065 (4)	0.003 (3)	0.024 (3)	0.008 (3)
C5	0.049 (3)	0.074 (4)	0.083 (4)	−0.010 (3)	0.026 (3)	0.011 (3)
C6	0.056 (3)	0.057 (3)	0.070 (4)	−0.015 (3)	0.021 (3)	0.007 (3)
C7	0.052 (3)	0.043 (3)	0.043 (3)	−0.004 (2)	0.015 (2)	0.0082 (19)
C8	0.067 (4)	0.045 (3)	0.055 (3)	−0.006 (3)	0.019 (3)	0.002 (2)
C9	0.063 (3)	0.042 (3)	0.053 (3)	0.010 (2)	0.015 (3)	0.000 (2)
C10	0.042 (3)	0.044 (3)	0.038 (2)	0.006 (2)	0.010 (2)	0.0034 (18)
C11	0.049 (3)	0.060 (3)	0.054 (3)	0.013 (3)	0.019 (2)	0.008 (2)
C12	0.037 (3)	0.057 (3)	0.068 (4)	0.002 (2)	0.016 (2)	0.003 (2)
C13	0.041 (3)	0.047 (3)	0.056 (3)	−0.004 (2)	0.010 (2)	0.002 (2)
C14	0.041 (2)	0.041 (2)	0.039 (2)	0.005 (2)	0.011 (2)	0.0055 (17)
C15	0.040 (2)	0.045 (3)	0.035 (2)	0.002 (2)	0.0122 (19)	0.0066 (17)
C16	0.050 (3)	0.048 (3)	0.043 (3)	0.005 (2)	0.013 (2)	−0.002 (2)
C17	0.061 (4)	0.049 (3)	0.075 (4)	0.005 (3)	0.023 (3)	−0.007 (3)
C18	0.065 (4)	0.061 (4)	0.072 (4)	−0.015 (3)	0.028 (3)	−0.011 (3)
C19	0.047 (3)	0.056 (3)	0.065 (3)	0.001 (2)	0.019 (3)	−0.003 (2)
C20	0.043 (3)	0.075 (4)	0.075 (4)	−0.004 (3)	0.023 (3)	−0.010 (3)
C21	0.053 (3)	0.069 (4)	0.073 (4)	−0.018 (3)	0.023 (3)	−0.006 (3)
C22	0.057 (3)	0.052 (3)	0.047 (3)	−0.006 (3)	0.013 (2)	−0.001 (2)
C23	0.072 (4)	0.049 (3)	0.064 (4)	−0.007 (3)	0.019 (3)	0.002 (2)
C24	0.078 (4)	0.045 (3)	0.062 (4)	0.004 (3)	0.015 (3)	−0.001 (2)
C25	0.057 (3)	0.050 (3)	0.052 (3)	0.010 (3)	0.011 (3)	−0.004 (2)
C26	0.061 (4)	0.067 (4)	0.056 (3)	0.021 (3)	0.010 (3)	−0.002 (3)
C27	0.051 (3)	0.075 (4)	0.073 (4)	0.018 (3)	0.022 (3)	−0.003 (3)
C28	0.048 (3)	0.066 (4)	0.059 (3)	0.006 (3)	0.021 (3)	0.004 (3)
C29	0.045 (3)	0.046 (3)	0.035 (2)	0.003 (2)	0.010 (2)	−0.0011 (18)
C30	0.041 (3)	0.047 (3)	0.044 (3)	0.002 (2)	0.009 (2)	−0.004 (2)

Geometric parameters (Å, º)

Cu1—N3	2.037 (4)	C7—C15	1.388 (7)
Cu1—N2	2.043 (4)	C7—C8	1.417 (8)
Cu1—S1	2.3015 (14)	C8—C9	1.342 (8)
Cu1—S2	2.3032 (16)	C8—H8A	0.9300
Cu1—I1	2.9334 (8)	C9—C10	1.419 (7)
Cu2—N5	2.042 (4)	C9—H9A	0.9300
Cu2—N6	2.051 (4)	C10—C14	1.405 (6)
Cu2—S4	2.3040 (15)	C10—C11	1.420 (7)
Cu2—S3	2.3078 (15)	C11—C12	1.346 (8)
Cu2—I2	2.8421 (8)	C11—H11A	0.9300
S1—C1	1.712 (6)	C12—C13	1.384 (7)
S2—C1	1.714 (5)	C12—H12A	0.9300
S3—C16	1.708 (6)	C13—H13A	0.9300
S4—C16	1.716 (5)	C14—C15	1.437 (7)
N1—C1	1.323 (6)	C17—H17A	0.9600
N1—C3	1.458 (8)	C17—H17B	0.9600
N1—C2	1.472 (7)	C17—H17C	0.9600
N2—C4	1.322 (6)	C18—H18A	0.9600
N2—C15	1.368 (6)	C18—H18B	0.9600
N3—C13	1.321 (6)	C18—H18C	0.9600
N3—C14	1.349 (6)	C19—C20	1.388 (8)
N4—C16	1.312 (7)	C19—H19A	0.9300
N4—C18	1.464 (7)	C20—C21	1.372 (9)
N4—C17	1.467 (7)	C20—H20A	0.9300
N5—C19	1.322 (7)	C21—C22	1.395 (8)
N5—C30	1.348 (6)	C21—H21A	0.9300
N6—C28	1.322 (6)	C22—C30	1.411 (7)
N6—C29	1.344 (6)	C22—C23	1.419 (8)
C2—H2A	0.9600	C23—C24	1.335 (8)
C2—H2B	0.9600	C23—H23A	0.9300
C2—H2C	0.9600	C24—C25	1.441 (9)
C3—H3A	0.9600	C24—H24A	0.9300
C3—H3B	0.9600	C25—C26	1.402 (8)
C3—H3C	0.9600	C25—C29	1.403 (7)
C4—C5	1.391 (9)	C26—C27	1.368 (9)
C4—H4A	0.9300	C26—H26A	0.9300
C5—C6	1.364 (9)	C27—C28	1.399 (8)
C5—H5A	0.9300	C27—H27A	0.9300
C6—C7	1.406 (7)	C28—H28A	0.9300
C6—H6A	0.9300	C29—C30	1.443 (7)
N3—Cu1—N2	81.32 (16)	C8—C9—C10	121.1 (5)
N3—Cu1—S1	164.60 (12)	C8—C9—H9A	119.4
N2—Cu1—S1	100.36 (12)	C10—C9—H9A	119.4
N3—Cu1—S2	98.25 (12)	C14—C10—C9	118.9 (5)
N2—Cu1—S2	167.68 (13)	C14—C10—C11	115.7 (5)
S1—Cu1—S2	76.82 (5)	C9—C10—C11	125.4 (5)
N3—Cu1—I1	87.74 (11)	C12—C11—C10	119.7 (5)
N2—Cu1—I1	91.36 (12)	C12—C11—H11A	120.2
S1—Cu1—I1	107.45 (4)	C10—C11—H11A	120.2
S2—Cu1—I1	100.94 (5)	C11—C12—C13	120.4 (5)
N5—Cu2—N6	81.00 (17)	C11—C12—H12A	119.8
N5—Cu2—S4	158.11 (13)	C13—C12—H12A	119.8
N6—Cu2—S4	98.62 (13)	N3—C13—C12	122.3 (5)
N5—Cu2—S3	97.36 (12)	N3—C13—H13A	118.9
N6—Cu2—S3	164.24 (13)	C12—C13—H13A	118.9
S4—Cu2—S3	77.04 (5)	N3—C14—C10	123.6 (4)
N5—Cu2—I2	95.88 (12)	N3—C14—C15	117.4 (4)
N6—Cu2—I2	98.70 (12)	C10—C14—C15	119.0 (4)
S4—Cu2—I2	105.76 (5)	N2—C15—C7	123.5 (4)
S3—Cu2—I2	97.07 (5)	N2—C15—C14	116.0 (4)
C1—S1—Cu1	85.00 (17)	C7—C15—C14	120.5 (4)
C1—S2—Cu1	84.90 (19)	N4—C16—S3	122.9 (4)
C16—S3—Cu2	84.50 (18)	N4—C16—S4	123.1 (4)
C16—S4—Cu2	84.44 (19)	S3—C16—S4	114.0 (3)
C1—N1—C3	121.5 (5)	N4—C17—H17A	109.5
C1—N1—C2	121.3 (5)	N4—C17—H17B	109.5
C3—N1—C2	117.2 (5)	H17A—C17—H17B	109.5
C4—N2—C15	117.3 (5)	N4—C17—H17C	109.5
C4—N2—Cu1	130.8 (4)	H17A—C17—H17C	109.5
C15—N2—Cu1	111.4 (3)	H17B—C17—H17C	109.5
C13—N3—C14	118.2 (4)	N4—C18—H18A	109.5
C13—N3—Cu1	129.1 (4)	N4—C18—H18B	109.5
C14—N3—Cu1	111.5 (3)	H18A—C18—H18B	109.5
C16—N4—C18	122.4 (5)	N4—C18—H18C	109.5
C16—N4—C17	120.7 (5)	H18A—C18—H18C	109.5
C18—N4—C17	117.0 (5)	H18B—C18—H18C	109.5
C19—N5—C30	118.5 (5)	N5—C19—C20	122.7 (5)
C19—N5—Cu2	128.8 (4)	N5—C19—H19A	118.7
C30—N5—Cu2	112.5 (3)	C20—C19—H19A	118.7
C28—N6—C29	117.9 (5)	C21—C20—C19	118.9 (5)
C28—N6—Cu2	129.6 (4)	C21—C20—H20A	120.5
C29—N6—Cu2	112.4 (3)	C19—C20—H20A	120.5
N1—C1—S1	124.2 (4)	C20—C21—C22	120.5 (5)
N1—C1—S2	122.6 (4)	C20—C21—H21A	119.8
S1—C1—S2	113.2 (3)	C22—C21—H21A	119.8
N1—C2—H2A	109.5	C21—C22—C30	116.2 (5)
N1—C2—H2B	109.5	C21—C22—C23	125.5 (5)
H2A—C2—H2B	109.5	C30—C22—C23	118.3 (5)
N1—C2—H2C	109.5	C24—C23—C22	122.3 (6)
H2A—C2—H2C	109.5	C24—C23—H23A	118.8
H2B—C2—H2C	109.5	C22—C23—H23A	118.8
N1—C3—H3A	109.5	C23—C24—C25	121.3 (6)
N1—C3—H3B	109.5	C23—C24—H24A	119.4
H3A—C3—H3B	109.5	C25—C24—H24A	119.4
N1—C3—H3C	109.5	C26—C25—C29	117.1 (6)
H3A—C3—H3C	109.5	C26—C25—C24	124.5 (5)
H3B—C3—H3C	109.5	C29—C25—C24	118.4 (5)
N2—C4—C5	123.3 (6)	C27—C26—C25	119.3 (6)
N2—C4—H4A	118.4	C27—C26—H26A	120.4
C5—C4—H4A	118.4	C25—C26—H26A	120.4
C6—C5—C4	119.1 (5)	C26—C27—C28	119.2 (6)
C6—C5—H5A	120.4	C26—C27—H27A	120.4
C4—C5—H5A	120.4	C28—C27—H27A	120.4
C5—C6—C7	119.8 (5)	N6—C28—C27	123.0 (6)
C5—C6—H6A	120.1	N6—C28—H28A	118.5
C7—C6—H6A	120.1	C27—C28—H28A	118.5
C15—C7—C6	116.9 (5)	N6—C29—C25	123.5 (5)
C15—C7—C8	118.5 (5)	N6—C29—C30	116.8 (4)
C6—C7—C8	124.5 (5)	C25—C29—C30	119.7 (5)
C9—C8—C7	121.9 (5)	N5—C30—C22	123.2 (5)
C9—C8—H8A	119.1	N5—C30—C29	116.9 (4)
C7—C8—H8A	119.1	C22—C30—C29	119.9 (5)