(1-Cyclo­pentano-4-ethyl-3-thio­semi­carbazone)­iodobis­(triphenyl­phosphino)copper(I) acetonitrile disolvate

Reaction of cyclo­penta­none N⁴-ethyl­thio­semicarbazone with copper (I) iodide in the presence of triphenyl phosphine as a coligand resulted in the formation of the title compound, which crystallized as the acetonitrile solvate, C₄₄H₄₅CuIN₃P₂S·2CH₃CN or [CuI(C₈H₁₅N₃S)(C₁₈H₁₅P)₂]·2C₂H₃N. The monomeric form of the complex has a slightly distorted tetra­hedral Cu coordinated by the S atom of the thio­semicarbazone ligand, with a Cu-S distance 2.3516 (7) Å. The Cu-P distances are 2.2876 (7) and 2.2959 (7) Å, and the Cu-I distance is 2.6547 (4) Å. One of the NH groups of the thio­semicarbazone forms an intra­molecular hydrogen bond with the I atom, while the other NH group forms a hydrogen bond to a solvent mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 115 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.030
• wR factor = 0.068
• Data-to-parameter ratio = 25.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  I1     -   Cu1     ..       9.58 su

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           30.50
           From the CIF: _reflns_number_total              13660
           Count of symmetry unique reflns         7718
           Completeness (_total/calc)            176.99%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      5942
           Fraction of Friedel pairs measured     0.770
           Are heavy atom types Z>Si present        yes

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

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: COLLECT (Nonius, 2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

[CuI(C8H15N3S)(C18H15P)2]·2C2H3N	F(000) = 2008
Mr = 982.38	Dx = 1.425 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7217 reflections
a = 9.9386 (10) Å	θ = 2.5–30.5°
b = 13.2986 (15) Å	µ = 1.31 mm^−1
c = 34.655 (4) Å	T = 115 K
V = 4580.3 (9) Å^3	Fragment, colorless
Z = 4	0.30 × 0.27 × 0.25 mm

Data collection

KappaCCD (with Oxford Cryostream) diffractometer	13660 independent reflections
Radiation source: fine-focus sealed tube	12568 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
ω scans with κ offsets	θmax = 30.5°, θmin = 2.6°
Absorption correction: multi-scan (HKL Scalepack; Otwinowski & Minor 1997)	h = −13→13
Tmin = 0.696, Tmax = 0.736	k = −18→19
33871 measured reflections	l = −48→48

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.030	w = 1/[σ^2(Fo^2) + (0.0227P)^2 + 3.9323P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.068	(Δ/σ)max = 0.002
S = 1.03	Δρmax = 0.55 e Å^−3
13660 reflections	Δρmin = −0.59 e Å^−3
533 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00061 (10)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 5940 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.015 (8)

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
I1	0.131038 (14)	0.523718 (12)	0.394175 (4)	0.02299 (4)
Cu1	0.38538 (3)	0.56997 (2)	0.378920 (8)	0.01806 (6)
S1	0.53118 (6)	0.50410 (4)	0.426005 (18)	0.02225 (12)
P1	0.44800 (6)	0.49368 (4)	0.322548 (17)	0.01827 (11)
P2	0.41481 (6)	0.73950 (4)	0.388189 (17)	0.01752 (11)
N1	0.3753 (2)	0.23801 (15)	0.44765 (6)	0.0252 (4)
N2	0.3844 (2)	0.34059 (15)	0.44033 (6)	0.0231 (4)
H2N	0.314 (3)	0.375 (2)	0.4329 (9)	0.028*
N3	0.6115 (2)	0.32017 (16)	0.44643 (7)	0.0251 (4)
H3N	0.593 (3)	0.258 (2)	0.4497 (9)	0.030*
C1	0.2428 (3)	0.0863 (2)	0.45356 (9)	0.0304 (6)
H1A	0.2490	0.0691	0.4813	0.036*
H1B	0.3118	0.0479	0.4391	0.036*
C2	0.1016 (3)	0.0656 (2)	0.43780 (10)	0.0356 (6)
H2A	0.1043	0.0541	0.4096	0.043*
H2B	0.0616	0.0059	0.4504	0.043*
C3	0.0222 (3)	0.1594 (2)	0.44729 (10)	0.0345 (6)
H3A	−0.0083	0.1587	0.4745	0.041*
H3B	−0.0571	0.1660	0.4302	0.041*
C4	0.1230 (3)	0.24545 (17)	0.44026 (8)	0.0266 (5)
H4A	0.1159	0.2709	0.4135	0.032*
H4B	0.1069	0.3018	0.4584	0.032*
C5	0.2591 (3)	0.1986 (2)	0.44727 (8)	0.0247 (5)
C6	0.5091 (2)	0.38010 (19)	0.43771 (7)	0.0218 (5)
C7	0.7533 (3)	0.3473 (2)	0.44193 (8)	0.0266 (5)
H7A	0.8083	0.3074	0.4602	0.032*
H7B	0.7654	0.4193	0.4483	0.032*
C8	0.8015 (3)	0.3283 (2)	0.40118 (9)	0.0355 (6)
H8A	0.7929	0.2566	0.3952	0.053*
H8B	0.8960	0.3485	0.3989	0.053*
H8C	0.7468	0.3675	0.3831	0.053*
C9	0.6010 (2)	0.54939 (17)	0.30239 (6)	0.0188 (4)
C10	0.5984 (3)	0.60618 (19)	0.26847 (7)	0.0237 (5)
H10	0.5194	0.6073	0.2531	0.028*
C11	0.7112 (3)	0.6614 (2)	0.25702 (8)	0.0291 (5)
H11	0.7082	0.7001	0.2340	0.035*
C12	0.8269 (3)	0.6598 (2)	0.27909 (8)	0.0292 (6)
H12	0.9026	0.6986	0.2716	0.035*
C13	0.8328 (3)	0.6012 (2)	0.31238 (8)	0.0290 (6)
H13	0.9135	0.5979	0.3270	0.035*
C14	0.7195 (2)	0.54764 (19)	0.32406 (8)	0.0252 (5)
H14	0.7229	0.5092	0.3472	0.030*
C15	0.3371 (2)	0.48823 (18)	0.28023 (6)	0.0206 (4)
C16	0.3690 (3)	0.42599 (19)	0.24898 (7)	0.0267 (5)
H16	0.4471	0.3849	0.2501	0.032*
C17	0.2875 (3)	0.4236 (2)	0.21641 (8)	0.0288 (5)
H17	0.3096	0.3809	0.1954	0.035*
C18	0.1741 (3)	0.4838 (2)	0.21474 (8)	0.0302 (5)
H18	0.1191	0.4831	0.1923	0.036*
C19	0.1406 (3)	0.5448 (2)	0.24549 (7)	0.0325 (6)
H19	0.0619	0.5853	0.2443	0.039*
C20	0.2220 (3)	0.5473 (2)	0.27846 (8)	0.0268 (5)
H20	0.1986	0.5894	0.2996	0.032*
C21	0.4841 (2)	0.35956 (18)	0.32848 (7)	0.0211 (5)
C22	0.3825 (3)	0.30163 (18)	0.34539 (7)	0.0268 (5)
H22	0.3033	0.3333	0.3548	0.032*
C23	0.3970 (3)	0.1974 (2)	0.34852 (8)	0.0340 (6)
H23	0.3277	0.1584	0.3600	0.041*
C24	0.5123 (3)	0.1512 (2)	0.33490 (8)	0.0343 (6)
H24	0.5212	0.0801	0.3364	0.041*
C25	0.6150 (3)	0.2082 (2)	0.31903 (8)	0.0337 (6)
H25	0.6951	0.1766	0.3103	0.040*
C26	0.6006 (3)	0.3122 (2)	0.31585 (8)	0.0271 (5)
H26	0.6713	0.3510	0.3049	0.033*
C27	0.3308 (2)	0.81491 (18)	0.35109 (7)	0.0210 (5)
C28	0.3384 (3)	0.7797 (2)	0.31352 (8)	0.0333 (6)
H28	0.3864	0.7195	0.3082	0.040*
C29	0.2769 (4)	0.8311 (3)	0.28358 (9)	0.0409 (7)
H29	0.2823	0.8056	0.2580	0.049*
C30	0.2074 (3)	0.9195 (2)	0.29068 (9)	0.0333 (6)
H30	0.1660	0.9550	0.2701	0.040*
C31	0.1990 (3)	0.9555 (2)	0.32805 (9)	0.0337 (6)
H31	0.1516	1.0160	0.3332	0.040*
C32	0.2598 (3)	0.9033 (2)	0.35810 (8)	0.0294 (6)
H32	0.2528	0.9282	0.3837	0.035*
C33	0.5840 (2)	0.79416 (18)	0.38887 (7)	0.0204 (4)
C34	0.6952 (2)	0.7308 (2)	0.39128 (8)	0.0266 (5)
H34	0.6825	0.6600	0.3924	0.032*
C35	0.8256 (3)	0.7705 (2)	0.39206 (9)	0.0345 (6)
H35	0.9009	0.7268	0.3940	0.041*
C36	0.8448 (3)	0.8733 (2)	0.39008 (8)	0.0337 (6)
H36	0.9334	0.9002	0.3900	0.040*
C37	0.7346 (3)	0.9374 (2)	0.38818 (8)	0.0303 (6)
H37	0.7480	1.0081	0.3873	0.036*
C38	0.6052 (3)	0.89845 (18)	0.38761 (7)	0.0259 (5)
H38	0.5303	0.9427	0.3864	0.031*
C39	0.3435 (3)	0.78572 (17)	0.43348 (7)	0.0223 (5)
C40	0.2040 (3)	0.7821 (2)	0.43847 (8)	0.0279 (5)
H40	0.1484	0.7588	0.4180	0.033*
C41	0.1461 (3)	0.8121 (2)	0.47299 (9)	0.0379 (7)
H41	0.0511	0.8102	0.4760	0.046*
C42	0.2264 (4)	0.8449 (2)	0.50314 (9)	0.0407 (8)
H42	0.1867	0.8654	0.5268	0.049*
C43	0.3648 (4)	0.8479 (2)	0.49860 (8)	0.0373 (7)
H43	0.4201	0.8702	0.5193	0.045*
C44	0.4235 (3)	0.8183 (2)	0.46385 (7)	0.0277 (5)
H44	0.5185	0.8205	0.4609	0.033*
N4	0.6736 (3)	0.1065 (2)	0.47134 (9)	0.0432 (7)
C45	0.7155 (3)	0.0326 (2)	0.48230 (8)	0.0293 (5)
C46	0.7698 (3)	−0.0620 (2)	0.49641 (9)	0.0339 (6)
H46A	0.7785	−0.1094	0.4749	0.051*
H46B	0.7091	−0.0902	0.5159	0.051*
H46C	0.8584	−0.0503	0.5079	0.051*
N5	−0.0053 (3)	0.6705 (2)	0.16212 (10)	0.0532 (8)
C47	−0.0110 (3)	0.7467 (2)	0.17706 (9)	0.0361 (6)
C48	−0.0177 (4)	0.8437 (3)	0.19581 (10)	0.0454 (8)
H48A	−0.0981	0.8467	0.2122	0.068*
H48B	−0.0223	0.8968	0.1762	0.068*
H48C	0.0627	0.8534	0.2118	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01624 (6)	0.02426 (7)	0.02846 (7)	−0.00035 (6)	−0.00024 (6)	0.00141 (6)
Cu1	0.01731 (13)	0.01671 (12)	0.02018 (12)	0.00132 (11)	0.00015 (10)	−0.00003 (10)
S1	0.0213 (3)	0.0184 (3)	0.0271 (3)	−0.00054 (19)	−0.0061 (2)	0.0025 (2)
P1	0.0176 (3)	0.0185 (3)	0.0187 (3)	0.0011 (2)	−0.0003 (2)	−0.0007 (2)
P2	0.0166 (2)	0.0164 (3)	0.0195 (3)	0.00173 (19)	0.0006 (2)	0.0009 (2)
N1	0.0241 (10)	0.0193 (9)	0.0322 (10)	0.0002 (9)	−0.0015 (9)	0.0045 (8)
N2	0.0207 (10)	0.0180 (9)	0.0306 (10)	0.0028 (8)	−0.0029 (9)	0.0034 (8)
N3	0.0204 (10)	0.0185 (9)	0.0363 (11)	0.0008 (8)	−0.0024 (9)	0.0053 (8)
C1	0.0306 (13)	0.0185 (12)	0.0421 (16)	−0.0005 (10)	−0.0053 (11)	0.0034 (11)
C2	0.0309 (14)	0.0204 (12)	0.0554 (18)	−0.0022 (11)	−0.0023 (12)	−0.0005 (12)
C3	0.0275 (14)	0.0263 (14)	0.0497 (18)	−0.0016 (11)	−0.0022 (12)	0.0034 (13)
C4	0.0240 (11)	0.0169 (10)	0.0388 (13)	0.0006 (10)	−0.0023 (11)	0.0014 (9)
C5	0.0260 (12)	0.0211 (12)	0.0272 (13)	0.0020 (9)	−0.0035 (10)	0.0013 (9)
C6	0.0211 (11)	0.0237 (12)	0.0205 (11)	0.0023 (9)	−0.0016 (9)	0.0016 (9)
C7	0.0185 (11)	0.0277 (13)	0.0337 (14)	0.0024 (9)	−0.0031 (10)	0.0011 (11)
C8	0.0274 (13)	0.0422 (17)	0.0369 (16)	0.0059 (12)	−0.0020 (11)	0.0089 (13)
C9	0.0173 (10)	0.0183 (10)	0.0209 (10)	0.0017 (7)	0.0011 (8)	−0.0016 (8)
C10	0.0256 (12)	0.0223 (11)	0.0231 (11)	0.0010 (9)	0.0008 (9)	0.0018 (9)
C11	0.0315 (14)	0.0255 (13)	0.0304 (13)	−0.0011 (11)	0.0061 (11)	0.0047 (11)
C12	0.0253 (12)	0.0260 (13)	0.0361 (14)	−0.0027 (10)	0.0101 (11)	−0.0008 (11)
C13	0.0224 (12)	0.0319 (14)	0.0327 (14)	0.0003 (10)	0.0000 (10)	−0.0025 (11)
C14	0.0222 (11)	0.0252 (13)	0.0281 (12)	0.0016 (9)	−0.0021 (10)	0.0024 (10)
C15	0.0218 (10)	0.0198 (11)	0.0202 (10)	−0.0010 (8)	−0.0020 (8)	0.0012 (9)
C16	0.0288 (12)	0.0263 (12)	0.0250 (11)	0.0037 (12)	−0.0030 (11)	−0.0017 (9)
C17	0.0354 (14)	0.0289 (13)	0.0222 (12)	−0.0020 (11)	−0.0052 (10)	−0.0020 (10)
C18	0.0266 (12)	0.0375 (15)	0.0264 (12)	−0.0033 (11)	−0.0065 (9)	0.0038 (12)
C19	0.0221 (12)	0.0458 (16)	0.0297 (12)	0.0077 (11)	−0.0028 (10)	0.0055 (11)
C20	0.0231 (11)	0.0329 (15)	0.0245 (12)	0.0055 (10)	0.0015 (9)	0.0006 (10)
C21	0.0259 (11)	0.0187 (11)	0.0188 (11)	0.0022 (9)	−0.0033 (9)	−0.0004 (9)
C22	0.0323 (13)	0.0211 (11)	0.0271 (12)	0.0007 (11)	0.0031 (11)	−0.0017 (9)
C23	0.0492 (18)	0.0232 (12)	0.0295 (13)	−0.0062 (12)	0.0059 (12)	−0.0005 (10)
C24	0.0543 (18)	0.0184 (12)	0.0303 (14)	0.0051 (12)	−0.0085 (13)	−0.0001 (11)
C25	0.0362 (15)	0.0267 (12)	0.0384 (14)	0.0118 (12)	−0.0019 (13)	−0.0019 (11)
C26	0.0243 (13)	0.0243 (12)	0.0327 (13)	0.0043 (9)	−0.0005 (10)	−0.0018 (10)
C27	0.0209 (11)	0.0187 (11)	0.0235 (11)	0.0007 (8)	−0.0010 (9)	0.0030 (9)
C28	0.0437 (17)	0.0328 (14)	0.0235 (12)	0.0139 (12)	0.0018 (11)	0.0035 (11)
C29	0.058 (2)	0.0414 (18)	0.0230 (14)	0.0147 (15)	−0.0038 (13)	0.0042 (12)
C30	0.0343 (14)	0.0320 (15)	0.0337 (14)	0.0031 (12)	−0.0067 (11)	0.0105 (12)
C31	0.0366 (14)	0.0244 (14)	0.0402 (15)	0.0069 (11)	−0.0090 (12)	0.0020 (11)
C32	0.0345 (14)	0.0241 (13)	0.0296 (14)	0.0071 (11)	−0.0060 (11)	−0.0009 (10)
C33	0.0196 (10)	0.0239 (11)	0.0177 (11)	−0.0019 (8)	−0.0008 (8)	−0.0011 (9)
C34	0.0201 (11)	0.0271 (12)	0.0326 (13)	0.0000 (9)	0.0005 (10)	−0.0043 (11)
C35	0.0200 (11)	0.0429 (16)	0.0407 (15)	−0.0018 (10)	−0.0016 (11)	−0.0047 (14)
C36	0.0268 (13)	0.0444 (16)	0.0299 (13)	−0.0141 (11)	−0.0006 (11)	−0.0028 (12)
C37	0.0346 (13)	0.0300 (13)	0.0263 (13)	−0.0114 (11)	0.0000 (10)	0.0005 (10)
C38	0.0285 (12)	0.0216 (11)	0.0275 (12)	−0.0025 (9)	−0.0004 (10)	0.0015 (9)
C39	0.0297 (13)	0.0150 (10)	0.0222 (11)	0.0032 (9)	0.0050 (9)	0.0013 (8)
C40	0.0273 (13)	0.0219 (12)	0.0343 (14)	0.0020 (10)	0.0092 (11)	0.0020 (11)
C41	0.0406 (17)	0.0245 (13)	0.0487 (17)	0.0105 (12)	0.0232 (14)	0.0074 (12)
C42	0.065 (2)	0.0262 (14)	0.0312 (15)	0.0164 (14)	0.0239 (15)	0.0057 (12)
C43	0.0615 (19)	0.0292 (13)	0.0213 (12)	0.0100 (15)	0.0052 (14)	−0.0008 (10)
C44	0.0361 (14)	0.0267 (13)	0.0203 (12)	0.0049 (10)	0.0020 (10)	0.0017 (10)
N4	0.0451 (15)	0.0313 (13)	0.0531 (17)	0.0056 (11)	−0.0010 (13)	0.0069 (12)
C45	0.0281 (12)	0.0278 (13)	0.0319 (13)	−0.0017 (11)	−0.0004 (10)	0.0004 (11)
C46	0.0412 (16)	0.0297 (14)	0.0309 (14)	0.0042 (12)	−0.0019 (12)	0.0017 (12)
N5	0.0551 (19)	0.0405 (17)	0.064 (2)	−0.0139 (14)	−0.0063 (16)	0.0047 (16)
C47	0.0277 (14)	0.0391 (16)	0.0414 (16)	−0.0065 (12)	−0.0023 (12)	0.0128 (14)
C48	0.0458 (19)	0.0454 (19)	0.0451 (18)	0.0041 (15)	−0.0038 (15)	0.0024 (16)

Geometric parameters (Å, º)

I1—Cu1	2.6547 (4)	C19—H19	0.9500
Cu1—P1	2.2876 (7)	C20—H20	0.9500
Cu1—P2	2.2959 (7)	C21—C26	1.389 (3)
Cu1—S1	2.3516 (7)	C21—C22	1.399 (4)
S1—C6	1.712 (3)	C22—C23	1.397 (4)
P1—C9	1.830 (2)	C22—H22	0.9500
P1—C21	1.831 (2)	C23—C24	1.384 (4)
P1—C15	1.836 (2)	C23—H23	0.9500
P2—C39	1.829 (2)	C24—C25	1.385 (4)
P2—C27	1.832 (2)	C24—H24	0.9500
P2—C33	1.832 (2)	C25—C26	1.394 (4)
N1—C5	1.268 (3)	C25—H25	0.9500
N1—N2	1.390 (3)	C26—H26	0.9500
N2—C6	1.349 (3)	C27—C28	1.386 (4)
N2—H2N	0.87 (3)	C27—C32	1.392 (4)
N3—C6	1.328 (3)	C28—C29	1.385 (4)
N3—C7	1.463 (3)	C28—H28	0.9500
N3—H3N	0.86 (3)	C29—C30	1.385 (4)
C1—C5	1.517 (4)	C29—H29	0.9500
C1—C2	1.531 (4)	C30—C31	1.383 (4)
C1—H1A	0.9900	C30—H30	0.9500
C1—H1B	0.9900	C31—C32	1.390 (4)
C2—C3	1.513 (4)	C31—H31	0.9500
C2—H2A	0.9900	C32—H32	0.9500
C2—H2B	0.9900	C33—C34	1.392 (3)
C3—C4	1.540 (4)	C33—C38	1.404 (3)
C3—H3A	0.9900	C34—C35	1.400 (3)
C3—H3B	0.9900	C34—H34	0.9500
C4—C5	1.509 (4)	C35—C36	1.382 (4)
C4—H4A	0.9900	C35—H35	0.9500
C4—H4B	0.9900	C36—C37	1.389 (4)
C7—C8	1.512 (4)	C36—H36	0.9500
C7—H7A	0.9900	C37—C38	1.387 (4)
C7—H7B	0.9900	C37—H37	0.9500
C8—H8A	0.9800	C38—H38	0.9500
C8—H8B	0.9800	C39—C44	1.388 (4)
C8—H8C	0.9800	C39—C40	1.398 (4)
C9—C10	1.397 (3)	C40—C41	1.387 (4)
C9—C14	1.398 (3)	C40—H40	0.9500
C10—C11	1.397 (4)	C41—C42	1.385 (5)
C10—H10	0.9500	C41—H41	0.9500
C11—C12	1.382 (4)	C42—C43	1.386 (5)
C11—H11	0.9500	C42—H42	0.9500
C12—C13	1.393 (4)	C43—C44	1.394 (4)
C12—H12	0.9500	C43—H43	0.9500
C13—C14	1.393 (4)	C44—H44	0.9500
C13—H13	0.9500	N4—C45	1.133 (4)
C14—H14	0.9500	C45—C46	1.454 (4)
C15—C20	1.389 (3)	C46—H46A	0.9800
C15—C16	1.399 (3)	C46—H46B	0.9800
C16—C17	1.389 (4)	C46—H46C	0.9800
C16—H16	0.9500	N5—C47	1.139 (4)
C17—C18	1.383 (4)	C47—C48	1.446 (5)
C17—H17	0.9500	C48—H48A	0.9800
C18—C19	1.381 (4)	C48—H48B	0.9800
C18—H18	0.9500	C48—H48C	0.9800
C19—C20	1.401 (4)
P1—Cu1—P2	121.35 (2)	C19—C18—C17	120.3 (2)
P1—Cu1—S1	105.05 (2)	C19—C18—H18	119.8
P2—Cu1—S1	100.97 (2)	C17—C18—H18	119.8
P1—Cu1—I1	109.046 (18)	C18—C19—C20	120.3 (2)
P2—Cu1—I1	108.722 (18)	C18—C19—H19	119.9
S1—Cu1—I1	111.239 (19)	C20—C19—H19	119.9
C6—S1—Cu1	116.37 (9)	C15—C20—C19	119.9 (2)
C9—P1—C21	105.92 (11)	C15—C20—H20	120.1
C9—P1—C15	102.11 (10)	C19—C20—H20	120.1
C21—P1—C15	99.73 (11)	C26—C21—C22	119.0 (2)
C9—P1—Cu1	111.87 (8)	C26—C21—P1	124.8 (2)
C21—P1—Cu1	112.93 (8)	C22—C21—P1	116.21 (19)
C15—P1—Cu1	122.43 (8)	C23—C22—C21	120.3 (3)
C39—P2—C27	103.99 (11)	C23—C22—H22	119.9
C39—P2—C33	102.20 (11)	C21—C22—H22	119.9
C27—P2—C33	102.13 (11)	C24—C23—C22	120.0 (3)
C39—P2—Cu1	113.63 (8)	C24—C23—H23	120.0
C27—P2—Cu1	112.42 (8)	C22—C23—H23	120.0
C33—P2—Cu1	120.55 (8)	C23—C24—C25	120.1 (3)
C5—N1—N2	117.6 (2)	C23—C24—H24	119.9
C6—N2—N1	117.0 (2)	C25—C24—H24	119.9
C6—N2—H2N	121 (2)	C24—C25—C26	120.0 (3)
N1—N2—H2N	121 (2)	C24—C25—H25	120.0
C6—N3—C7	124.5 (2)	C26—C25—H25	120.0
C6—N3—H3N	116 (2)	C21—C26—C25	120.7 (3)
C7—N3—H3N	118 (2)	C21—C26—H26	119.7
C5—C1—C2	102.9 (2)	C25—C26—H26	119.7
C5—C1—H1A	111.2	C28—C27—C32	118.5 (2)
C2—C1—H1A	111.2	C28—C27—P2	116.73 (19)
C5—C1—H1B	111.2	C32—C27—P2	124.8 (2)
C2—C1—H1B	111.2	C29—C28—C27	120.9 (3)
H1A—C1—H1B	109.1	C29—C28—H28	119.6
C3—C2—C1	104.6 (2)	C27—C28—H28	119.6
C3—C2—H2A	110.8	C28—C29—C30	120.4 (3)
C1—C2—H2A	110.8	C28—C29—H29	119.8
C3—C2—H2B	110.8	C30—C29—H29	119.8
C1—C2—H2B	110.8	C31—C30—C29	119.3 (3)
H2A—C2—H2B	108.9	C31—C30—H30	120.3
C2—C3—C4	103.8 (2)	C29—C30—H30	120.3
C2—C3—H3A	111.0	C30—C31—C32	120.2 (3)
C4—C3—H3A	111.0	C30—C31—H31	119.9
C2—C3—H3B	111.0	C32—C31—H31	119.9
C4—C3—H3B	111.0	C31—C32—C27	120.8 (3)
H3A—C3—H3B	109.0	C31—C32—H32	119.6
C5—C4—C3	104.5 (2)	C27—C32—H32	119.6
C5—C4—H4A	110.8	C34—C33—C38	118.8 (2)
C3—C4—H4A	110.8	C34—C33—P2	119.28 (19)
C5—C4—H4B	110.8	C38—C33—P2	121.95 (18)
C3—C4—H4B	110.8	C33—C34—C35	120.5 (2)
H4A—C4—H4B	108.9	C33—C34—H34	119.8
N1—C5—C4	130.3 (2)	C35—C34—H34	119.8
N1—C5—C1	120.2 (2)	C36—C35—C34	120.1 (3)
C4—C5—C1	109.5 (2)	C36—C35—H35	120.0
N3—C6—N2	117.1 (2)	C34—C35—H35	120.0
N3—C6—S1	122.25 (19)	C35—C36—C37	120.0 (2)
N2—C6—S1	120.58 (18)	C35—C36—H36	120.0
N3—C7—C8	111.3 (2)	C37—C36—H36	120.0
N3—C7—H7A	109.4	C38—C37—C36	120.2 (3)
C8—C7—H7A	109.4	C38—C37—H37	119.9
N3—C7—H7B	109.4	C36—C37—H37	119.9
C8—C7—H7B	109.4	C37—C38—C33	120.5 (2)
H7A—C7—H7B	108.0	C37—C38—H38	119.8
C7—C8—H8A	109.5	C33—C38—H38	119.8
C7—C8—H8B	109.5	C44—C39—C40	119.0 (2)
H8A—C8—H8B	109.5	C44—C39—P2	122.3 (2)
C7—C8—H8C	109.5	C40—C39—P2	118.6 (2)
H8A—C8—H8C	109.5	C41—C40—C39	120.6 (3)
H8B—C8—H8C	109.5	C41—C40—H40	119.7
C10—C9—C14	118.5 (2)	C39—C40—H40	119.7
C10—C9—P1	121.66 (18)	C42—C41—C40	120.1 (3)
C14—C9—P1	119.25 (18)	C42—C41—H41	119.9
C11—C10—C9	120.6 (2)	C40—C41—H41	119.9
C11—C10—H10	119.7	C41—C42—C43	119.7 (3)
C9—C10—H10	119.7	C41—C42—H42	120.1
C12—C11—C10	120.1 (3)	C43—C42—H42	120.1
C12—C11—H11	119.9	C42—C43—C44	120.3 (3)
C10—C11—H11	119.9	C42—C43—H43	119.8
C11—C12—C13	120.2 (2)	C44—C43—H43	119.8
C11—C12—H12	119.9	C39—C44—C43	120.2 (3)
C13—C12—H12	119.9	C39—C44—H44	119.9
C14—C13—C12	119.5 (2)	C43—C44—H44	119.9
C14—C13—H13	120.2	N4—C45—C46	179.7 (4)
C12—C13—H13	120.2	C45—C46—H46A	109.5
C13—C14—C9	121.1 (2)	C45—C46—H46B	109.5
C13—C14—H14	119.4	H46A—C46—H46B	109.5
C9—C14—H14	119.4	C45—C46—H46C	109.5
C20—C15—C16	119.2 (2)	H46A—C46—H46C	109.5
C20—C15—P1	120.48 (18)	H46B—C46—H46C	109.5
C16—C15—P1	120.36 (18)	N5—C47—C48	179.6 (4)
C17—C16—C15	120.7 (2)	C47—C48—H48A	109.5
C17—C16—H16	119.7	C47—C48—H48B	109.5
C15—C16—H16	119.7	H48A—C48—H48B	109.5
C18—C17—C16	119.7 (3)	C47—C48—H48C	109.5
C18—C17—H17	120.1	H48A—C48—H48C	109.5
C16—C17—H17	120.1	H48B—C48—H48C	109.5
P1—Cu1—S1—C6	−69.34 (10)	C16—C17—C18—C19	−1.0 (4)
P2—Cu1—S1—C6	163.72 (10)	C17—C18—C19—C20	0.8 (4)
I1—Cu1—S1—C6	48.50 (10)	C16—C15—C20—C19	−0.7 (4)
P2—Cu1—P1—C9	35.67 (9)	P1—C15—C20—C19	178.0 (2)
S1—Cu1—P1—C9	−77.56 (8)	C18—C19—C20—C15	0.0 (4)
I1—Cu1—P1—C9	163.12 (8)	C9—P1—C21—C26	−6.1 (2)
P2—Cu1—P1—C21	155.05 (9)	C15—P1—C21—C26	99.6 (2)
S1—Cu1—P1—C21	41.82 (9)	Cu1—P1—C21—C26	−128.9 (2)
I1—Cu1—P1—C21	−77.50 (9)	C9—P1—C21—C22	177.09 (19)
P2—Cu1—P1—C15	−85.86 (10)	C15—P1—C21—C22	−77.2 (2)
S1—Cu1—P1—C15	160.91 (9)	Cu1—P1—C21—C22	54.3 (2)
I1—Cu1—P1—C15	41.59 (9)	C26—C21—C22—C23	−1.7 (4)
P1—Cu1—P2—C39	174.68 (9)	P1—C21—C22—C23	175.3 (2)
S1—Cu1—P2—C39	−69.99 (9)	C21—C22—C23—C24	0.1 (4)
I1—Cu1—P2—C39	47.09 (9)	C22—C23—C24—C25	1.6 (4)
P1—Cu1—P2—C27	56.91 (9)	C23—C24—C25—C26	−1.7 (4)
S1—Cu1—P2—C27	172.24 (9)	C22—C21—C26—C25	1.6 (4)
I1—Cu1—P2—C27	−70.67 (9)	P1—C21—C26—C25	−175.1 (2)
P1—Cu1—P2—C33	−63.58 (9)	C24—C25—C26—C21	0.0 (4)
S1—Cu1—P2—C33	51.75 (9)	C39—P2—C27—C28	−163.8 (2)
I1—Cu1—P2—C33	168.83 (9)	C33—P2—C27—C28	90.1 (2)
C5—N1—N2—C6	−174.8 (2)	Cu1—P2—C27—C28	−40.5 (2)
C5—C1—C2—C3	−34.1 (3)	C39—P2—C27—C32	15.4 (3)
C1—C2—C3—C4	38.6 (3)	C33—P2—C27—C32	−90.6 (2)
C2—C3—C4—C5	−27.6 (3)	Cu1—P2—C27—C32	138.8 (2)
N2—N1—C5—C4	−0.5 (4)	C32—C27—C28—C29	0.0 (4)
N2—N1—C5—C1	177.7 (2)	P2—C27—C28—C29	179.4 (3)
C3—C4—C5—N1	−175.1 (3)	C27—C28—C29—C30	0.6 (5)
C3—C4—C5—C1	6.4 (3)	C28—C29—C30—C31	−0.6 (5)
C2—C1—C5—N1	−161.8 (3)	C29—C30—C31—C32	0.0 (5)
C2—C1—C5—C4	16.8 (3)	C30—C31—C32—C27	0.6 (5)
C7—N3—C6—N2	174.3 (2)	C28—C27—C32—C31	−0.6 (4)
C7—N3—C6—S1	−9.0 (4)	P2—C27—C32—C31	−179.9 (2)
N1—N2—C6—N3	−7.1 (3)	C39—P2—C33—C34	114.7 (2)
N1—N2—C6—S1	176.19 (17)	C27—P2—C33—C34	−137.9 (2)
Cu1—S1—C6—N3	144.53 (19)	Cu1—P2—C33—C34	−12.4 (2)
Cu1—S1—C6—N2	−38.9 (2)	C39—P2—C33—C38	−64.3 (2)
C6—N3—C7—C8	−84.4 (3)	C27—P2—C33—C38	43.1 (2)
C21—P1—C9—C10	125.9 (2)	Cu1—P2—C33—C38	168.53 (17)
C15—P1—C9—C10	22.0 (2)	C38—C33—C34—C35	−0.6 (4)
Cu1—P1—C9—C10	−110.62 (19)	P2—C33—C34—C35	−179.7 (2)
C21—P1—C9—C14	−63.4 (2)	C33—C34—C35—C36	−0.6 (4)
C15—P1—C9—C14	−167.32 (19)	C34—C35—C36—C37	1.5 (5)
Cu1—P1—C9—C14	60.1 (2)	C35—C36—C37—C38	−1.1 (4)
C14—C9—C10—C11	−1.3 (4)	C36—C37—C38—C33	−0.1 (4)
P1—C9—C10—C11	169.5 (2)	C34—C33—C38—C37	1.0 (4)
C9—C10—C11—C12	0.4 (4)	P2—C33—C38—C37	179.98 (19)
C10—C11—C12—C13	1.5 (4)	C27—P2—C39—C44	−126.9 (2)
C11—C12—C13—C14	−2.6 (4)	C33—P2—C39—C44	−20.9 (2)
C12—C13—C14—C9	1.7 (4)	Cu1—P2—C39—C44	110.5 (2)
C10—C9—C14—C13	0.2 (4)	C27—P2—C39—C40	57.2 (2)
P1—C9—C14—C13	−170.8 (2)	C33—P2—C39—C40	163.2 (2)
C9—P1—C15—C20	−113.2 (2)	Cu1—P2—C39—C40	−65.4 (2)
C21—P1—C15—C20	138.1 (2)	C44—C39—C40—C41	1.1 (4)
Cu1—P1—C15—C20	12.8 (2)	P2—C39—C40—C41	177.1 (2)
C9—P1—C15—C16	65.5 (2)	C39—C40—C41—C42	−0.8 (4)
C21—P1—C15—C16	−43.3 (2)	C40—C41—C42—C43	0.2 (4)
Cu1—P1—C15—C16	−168.53 (17)	C41—C42—C43—C44	0.2 (4)
C20—C15—C16—C17	0.5 (4)	C40—C39—C44—C43	−0.7 (4)
P1—C15—C16—C17	−178.2 (2)	P2—C39—C44—C43	−176.6 (2)
C15—C16—C17—C18	0.3 (4)	C42—C43—C44—C39	0.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···I1	0.87 (3)	3.00 (3)	3.851 (2)	164 (3)
N3—H3N···N4	0.86 (3)	2.29 (3)	3.033 (3)	145 (3)