[N,N-Bis(2-hy­droxy­eth­yl)di­thio­carbamato-κ²S,S′]bis­(tri­phenyl­phosphane-κP)copper(I) chloro­form monosolvate: crystal structure, Hirshfeld surface analysis and solution NMR measurements

A tetra­hedral CuP₂S₂ coordination geometry is found for the Cu^I ion in the title compound. The di­thio­cabamate ligand forms symmetric Cu—S bonds. In the crystal, supra­molecular dimers of complex mol­ecules are connected via eight-membered {...H—O...H—O}₂ synthons. In addition, the chloro­form mol­ecule participates in Cl...π(arene) and S...Cl inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.117
• Data-to-parameter ratio = 23.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of         C6 Check
PLAT431_ALERT_2_C Short Inter HL..A  Contact Cl3    ..  S1      ..       3.35 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min)           6 Note
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          4 Report
PLAT971_ALERT_2_C Check Calcd Residual Density  0.74A From     Cl1       1.99 eA-3
PLAT971_ALERT_2_C Check Calcd Residual Density  0.74A From      O1       1.62 eA-3
PLAT972_ALERT_2_C Check Calcd Residual Density  0.65A From     Cl1      -1.91 eA-3
PLAT972_ALERT_2_C Check Calcd Residual Density  0.75A From     Cl2      -1.79 eA-3
PLAT972_ALERT_2_C Check Calcd Residual Density  0.63A From     Cl1      -1.67 eA-3
PLAT972_ALERT_2_C Check Calcd Residual Density  0.39A From     Cl1      -1.64 eA-3
PLAT975_ALERT_2_C Check Calcd Residual Density  0.80A From      O2       0.63 eA-3
PLAT976_ALERT_2_C Check Calcd Residual Density  0.60A From      O1      -0.54 eA-3

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        774 Note
PLAT933_ALERT_2_G Number of OMIT records in Embedded RES .........          4 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density          10 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
  12 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.
PUBL022_ALERT_1_A There is a mismatched ~ on line 517
              (I).CHCl~3~ with a pair of symmetrical tips at <i>d</i>~e~ + <i>d</i>~i~ \~
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~

   2 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); cell refinement: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); data reduction: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

[N,N-Bis(2-hydroxyethyl)dithiocarbamato-κ²S,S']bis(triphenylphosphane-κP)copper(I) chloroform monosolvate

Crystal data

[Cu(C5H5NO2S2)(C18H15P)2]·CHCl3	Z = 2
Mr = 887.71	F(000) = 916
Triclinic, P1	Dx = 1.444 Mg m^−3
a = 10.7271 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.5412 (2) Å	Cell parameters from 38605 reflections
c = 15.9361 (3) Å	θ = 3.1–30.1°
α = 67.747 (2)°	µ = 0.95 mm^−1
β = 87.126 (2)°	T = 100 K
γ = 72.826 (2)°	Prism, colourless
V = 2041.92 (7) Å^3	0.44 × 0.24 × 0.19 mm

Data collection

Rigaku SuperNova, Dual Mo at zero, AtlasS2 diffractometer	11363 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	10195 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.029
Detector resolution: 5.2303 pixels mm^-1	θmax = 30.2°, θmin = 2.4°
ω scans	h = −14→14
Absorption correction: multi-scan (CrysAlis PRO; Rigaku Oxford Diffraction, 2015)	k = −19→18
Tmin = 0.928, Tmax = 1.000	l = −22→21
78295 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0542P)^2 + 3.7972P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.002
11363 reflections	Δρmax = 1.97 e Å^−3
478 parameters	Δρmin = −1.93 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu	0.36192 (2)	0.77121 (2)	0.71076 (2)	0.01300 (7)
S1	0.19989 (5)	0.72501 (4)	0.81318 (3)	0.01687 (10)
S2	0.18227 (5)	0.94266 (4)	0.66887 (3)	0.01434 (10)
P1	0.51698 (5)	0.80568 (4)	0.77705 (3)	0.01311 (10)
P2	0.40667 (5)	0.66266 (4)	0.62988 (3)	0.01279 (10)
O1	−0.0657 (2)	1.09492 (18)	0.86819 (14)	0.0388 (5)
H1O	−0.0221	1.1248	0.8899	0.058*
O2	−0.0552 (2)	0.89051 (18)	0.99446 (14)	0.0379 (5)
H2O	−0.0317	0.9473	0.9646	0.057*
N1	0.00449 (17)	0.90924 (16)	0.79337 (12)	0.0179 (3)
C1	0.11675 (19)	0.86434 (16)	0.76152 (13)	0.0138 (3)
C2	−0.0662 (2)	1.02862 (19)	0.74859 (15)	0.0222 (4)
H2A	−0.1600	1.0404	0.7600	0.027*
H2B	−0.0588	1.0517	0.6822	0.027*
C3	−0.0154 (3)	1.1018 (2)	0.78121 (17)	0.0274 (5)
H3A	0.0814	1.0761	0.7870	0.033*
H3B	−0.0444	1.1802	0.7370	0.033*
C4	−0.0538 (2)	0.8356 (2)	0.86728 (15)	0.0244 (5)
H4A	−0.0415	0.7655	0.8574	0.029*
H4B	−0.1491	0.8725	0.8635	0.029*
C5	0.0018 (2)	0.8061 (2)	0.96199 (16)	0.0276 (5)
H5A	−0.0136	0.7356	1.0035	0.033*
H5B	0.0974	0.7937	0.9613	0.033*
C11	0.4522 (2)	0.90455 (17)	0.83239 (13)	0.0155 (4)
C12	0.3587 (2)	0.88068 (19)	0.89530 (15)	0.0193 (4)
H12	0.3316	0.8164	0.9064	0.023*
C13	0.3054 (2)	0.9506 (2)	0.94159 (15)	0.0223 (4)
H13	0.2421	0.9338	0.9842	0.027*
C14	0.3446 (2)	1.0450 (2)	0.92569 (16)	0.0239 (4)
H14	0.3080	1.0928	0.9572	0.029*
C15	0.4374 (3)	1.0687 (2)	0.86363 (16)	0.0264 (5)
H15	0.4645	1.1330	0.8528	0.032*
C16	0.4912 (2)	0.99887 (18)	0.81703 (15)	0.0214 (4)
H16	0.5547	1.0158	0.7746	0.026*
C21	0.6312 (2)	0.86383 (16)	0.69950 (13)	0.0140 (3)
C22	0.5816 (2)	0.96097 (17)	0.62185 (14)	0.0186 (4)
H22	0.4900	0.9973	0.6120	0.022*
C23	0.6653 (2)	1.00436 (18)	0.55932 (15)	0.0221 (4)
H23	0.6308	1.0706	0.5072	0.027*
C24	0.7997 (2)	0.95133 (19)	0.57246 (15)	0.0212 (4)
H24	0.8568	0.9818	0.5298	0.025*
C25	0.8497 (2)	0.85403 (19)	0.64806 (14)	0.0196 (4)
H25	0.9411	0.8171	0.6568	0.024*
C26	0.7660 (2)	0.81042 (18)	0.71115 (14)	0.0169 (4)
H26	0.8009	0.7436	0.7627	0.020*
C31	0.6275 (2)	0.68849 (17)	0.86749 (13)	0.0162 (4)
C32	0.6884 (2)	0.70275 (19)	0.93539 (15)	0.0218 (4)
H32	0.6666	0.7743	0.9389	0.026*
C33	0.7811 (2)	0.6126 (2)	0.99804 (16)	0.0268 (5)
H33	0.8220	0.6228	1.0444	0.032*
C34	0.8138 (3)	0.5084 (2)	0.99318 (17)	0.0300 (5)
H34	0.8781	0.4474	1.0356	0.036*
C35	0.7531 (3)	0.4929 (2)	0.9266 (2)	0.0347 (6)
H35	0.7752	0.4211	0.9236	0.042*
C36	0.6593 (2)	0.58267 (19)	0.86396 (18)	0.0267 (5)
H36	0.6170	0.5716	0.8187	0.032*
C41	0.48854 (19)	0.51623 (16)	0.69995 (14)	0.0156 (4)
C42	0.5952 (2)	0.45035 (19)	0.67222 (16)	0.0220 (4)
H42	0.6255	0.4805	0.6136	0.026*
C43	0.6577 (2)	0.3406 (2)	0.73001 (18)	0.0272 (5)
H43	0.7300	0.2961	0.7105	0.033*
C44	0.6151 (2)	0.29608 (19)	0.81547 (18)	0.0273 (5)
H44	0.6593	0.2219	0.8552	0.033*
C45	0.5079 (3)	0.3600 (2)	0.84291 (17)	0.0273 (5)
H45	0.4773	0.3288	0.9012	0.033*
C46	0.4446 (2)	0.46945 (18)	0.78592 (16)	0.0223 (4)
H46	0.3711	0.5127	0.8055	0.027*
C51	0.26885 (19)	0.65508 (16)	0.57220 (13)	0.0135 (3)
C52	0.2709 (2)	0.55962 (17)	0.55691 (14)	0.0169 (4)
H52	0.3427	0.4937	0.5812	0.020*
C53	0.1684 (2)	0.56083 (18)	0.50627 (15)	0.0196 (4)
H53	0.1702	0.4958	0.4960	0.024*
C54	0.0630 (2)	0.65717 (19)	0.47064 (15)	0.0207 (4)
H54	−0.0067	0.6581	0.4355	0.025*
C55	0.0595 (2)	0.75232 (18)	0.48645 (15)	0.0192 (4)
H55	−0.0125	0.8181	0.4622	0.023*
C56	0.16193 (19)	0.75072 (17)	0.53791 (14)	0.0158 (4)
H56	0.1588	0.8151	0.5496	0.019*
C61	0.51483 (19)	0.69669 (16)	0.53792 (14)	0.0150 (4)
C62	0.4884 (2)	0.70661 (17)	0.44993 (14)	0.0179 (4)
H62	0.4136	0.6900	0.4363	0.021*
C63	0.5711 (2)	0.74078 (18)	0.38150 (16)	0.0225 (4)
H63	0.5526	0.7468	0.3218	0.027*
C64	0.6801 (2)	0.7659 (2)	0.40050 (18)	0.0266 (5)
H64	0.7356	0.7901	0.3538	0.032*
C65	0.7076 (2)	0.7553 (2)	0.4883 (2)	0.0295 (5)
H65	0.7827	0.7716	0.5018	0.035*
C66	0.6258 (2)	0.7211 (2)	0.55654 (17)	0.0237 (5)
H66	0.6454	0.7141	0.6164	0.028*
C6	0.0552 (3)	0.4509 (2)	0.7262 (2)	0.0354 (6)
H6	0.0901	0.4682	0.6646	0.042*
Cl1	0.14649 (11)	0.31507 (7)	0.79474 (7)	0.0593 (3)
Cl2	−0.10822 (9)	0.46142 (12)	0.71310 (9)	0.0740 (4)
Cl3	0.07466 (6)	0.55046 (5)	0.76719 (4)	0.03169 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu	0.01265 (12)	0.01232 (11)	0.01406 (12)	−0.00179 (8)	0.00184 (8)	−0.00664 (9)
S1	0.0200 (2)	0.0124 (2)	0.0169 (2)	−0.00543 (18)	0.00520 (18)	−0.00421 (17)
S2	0.0153 (2)	0.0118 (2)	0.0124 (2)	−0.00113 (16)	0.00266 (16)	−0.00311 (16)
P1	0.0136 (2)	0.0124 (2)	0.0123 (2)	−0.00270 (17)	0.00066 (17)	−0.00431 (17)
P2	0.0117 (2)	0.0117 (2)	0.0150 (2)	−0.00122 (17)	0.00111 (17)	−0.00678 (18)
O1	0.0411 (11)	0.0450 (12)	0.0303 (10)	0.0017 (9)	0.0000 (8)	−0.0252 (9)
O2	0.0432 (11)	0.0421 (11)	0.0300 (10)	−0.0052 (9)	0.0066 (8)	−0.0216 (9)
N1	0.0131 (8)	0.0227 (9)	0.0159 (8)	−0.0025 (7)	0.0033 (6)	−0.0078 (7)
C1	0.0134 (8)	0.0163 (9)	0.0125 (8)	−0.0043 (7)	0.0015 (7)	−0.0065 (7)
C2	0.0161 (9)	0.0255 (11)	0.0198 (10)	0.0043 (8)	−0.0011 (8)	−0.0107 (8)
C3	0.0300 (12)	0.0218 (11)	0.0257 (11)	0.0060 (9)	−0.0041 (9)	−0.0136 (9)
C4	0.0171 (10)	0.0363 (13)	0.0199 (10)	−0.0105 (9)	0.0076 (8)	−0.0097 (9)
C5	0.0244 (11)	0.0366 (13)	0.0182 (10)	−0.0062 (10)	0.0046 (8)	−0.0090 (9)
C11	0.0166 (9)	0.0161 (9)	0.0135 (9)	−0.0027 (7)	−0.0002 (7)	−0.0069 (7)
C12	0.0188 (10)	0.0219 (10)	0.0200 (10)	−0.0076 (8)	0.0039 (8)	−0.0103 (8)
C13	0.0220 (10)	0.0269 (11)	0.0194 (10)	−0.0055 (9)	0.0044 (8)	−0.0119 (9)
C14	0.0300 (12)	0.0234 (11)	0.0194 (10)	−0.0039 (9)	0.0027 (9)	−0.0126 (9)
C15	0.0400 (13)	0.0209 (10)	0.0233 (11)	−0.0130 (10)	0.0068 (10)	−0.0117 (9)
C16	0.0284 (11)	0.0194 (10)	0.0190 (10)	−0.0094 (8)	0.0055 (8)	−0.0090 (8)
C21	0.0178 (9)	0.0127 (8)	0.0120 (8)	−0.0049 (7)	0.0004 (7)	−0.0050 (7)
C22	0.0230 (10)	0.0134 (9)	0.0152 (9)	−0.0008 (7)	0.0012 (8)	−0.0046 (7)
C23	0.0335 (12)	0.0135 (9)	0.0153 (9)	−0.0054 (8)	0.0040 (8)	−0.0025 (7)
C24	0.0311 (11)	0.0200 (10)	0.0169 (10)	−0.0132 (9)	0.0084 (8)	−0.0083 (8)
C25	0.0191 (10)	0.0245 (10)	0.0171 (9)	−0.0087 (8)	0.0029 (8)	−0.0085 (8)
C26	0.0167 (9)	0.0187 (9)	0.0137 (9)	−0.0050 (7)	0.0002 (7)	−0.0047 (7)
C31	0.0153 (9)	0.0159 (9)	0.0132 (9)	−0.0052 (7)	0.0003 (7)	−0.0006 (7)
C32	0.0241 (11)	0.0226 (10)	0.0153 (9)	−0.0067 (8)	−0.0009 (8)	−0.0035 (8)
C33	0.0274 (12)	0.0311 (12)	0.0164 (10)	−0.0105 (10)	−0.0048 (8)	−0.0009 (9)
C34	0.0268 (12)	0.0241 (11)	0.0247 (12)	−0.0076 (9)	−0.0063 (9)	0.0073 (9)
C35	0.0373 (14)	0.0151 (10)	0.0410 (15)	−0.0023 (10)	−0.0130 (12)	−0.0012 (10)
C36	0.0292 (12)	0.0164 (10)	0.0299 (12)	−0.0050 (9)	−0.0087 (9)	−0.0038 (9)
C41	0.0146 (9)	0.0137 (8)	0.0183 (9)	−0.0020 (7)	−0.0018 (7)	−0.0072 (7)
C42	0.0199 (10)	0.0190 (10)	0.0232 (11)	0.0006 (8)	0.0000 (8)	−0.0085 (8)
C43	0.0213 (11)	0.0186 (10)	0.0339 (13)	0.0049 (8)	−0.0025 (9)	−0.0093 (9)
C44	0.0259 (11)	0.0158 (10)	0.0322 (12)	−0.0018 (8)	−0.0085 (9)	−0.0027 (9)
C45	0.0308 (12)	0.0188 (10)	0.0263 (12)	−0.0079 (9)	0.0009 (9)	−0.0017 (9)
C46	0.0218 (10)	0.0170 (10)	0.0249 (11)	−0.0042 (8)	0.0041 (8)	−0.0062 (8)
C51	0.0126 (8)	0.0146 (8)	0.0125 (8)	−0.0039 (7)	0.0032 (6)	−0.0049 (7)
C52	0.0156 (9)	0.0154 (9)	0.0198 (9)	−0.0023 (7)	0.0013 (7)	−0.0083 (7)
C53	0.0198 (10)	0.0201 (10)	0.0227 (10)	−0.0072 (8)	0.0031 (8)	−0.0116 (8)
C54	0.0156 (9)	0.0260 (11)	0.0214 (10)	−0.0068 (8)	0.0002 (8)	−0.0096 (8)
C55	0.0138 (9)	0.0177 (9)	0.0219 (10)	−0.0013 (7)	−0.0002 (7)	−0.0054 (8)
C56	0.0143 (9)	0.0137 (9)	0.0186 (9)	−0.0030 (7)	0.0035 (7)	−0.0064 (7)
C61	0.0131 (8)	0.0117 (8)	0.0209 (9)	−0.0018 (7)	0.0043 (7)	−0.0087 (7)
C62	0.0174 (9)	0.0152 (9)	0.0195 (10)	−0.0038 (7)	0.0037 (7)	−0.0060 (7)
C63	0.0245 (11)	0.0178 (10)	0.0205 (10)	−0.0044 (8)	0.0066 (8)	−0.0043 (8)
C64	0.0239 (11)	0.0217 (11)	0.0373 (13)	−0.0098 (9)	0.0165 (10)	−0.0142 (10)
C65	0.0198 (11)	0.0349 (13)	0.0484 (15)	−0.0146 (10)	0.0147 (10)	−0.0284 (12)
C66	0.0177 (10)	0.0309 (12)	0.0332 (12)	−0.0088 (9)	0.0075 (9)	−0.0231 (10)
C6	0.0351 (14)	0.0380 (14)	0.0356 (14)	−0.0135 (12)	−0.0031 (11)	−0.0143 (12)
Cl1	0.0739 (6)	0.0376 (4)	0.0688 (6)	−0.0043 (4)	−0.0159 (5)	−0.0297 (4)
Cl2	0.0320 (4)	0.1170 (9)	0.1089 (9)	−0.0168 (5)	−0.0041 (5)	−0.0847 (8)
Cl3	0.0340 (3)	0.0258 (3)	0.0323 (3)	−0.0095 (2)	−0.0041 (2)	−0.0067 (2)

Geometric parameters (Å, º)

Cu—P2	2.2380 (5)	C26—H26	0.9500
Cu—P1	2.2602 (6)	C31—C32	1.392 (3)
Cu—S1	2.3791 (6)	C31—C36	1.394 (3)
Cu—S2	2.4213 (5)	C32—C33	1.391 (3)
S1—C1	1.714 (2)	C32—H32	0.9500
S2—C1	1.717 (2)	C33—C34	1.381 (4)
P1—C31	1.824 (2)	C33—H33	0.9500
P1—C21	1.825 (2)	C34—C35	1.383 (4)
P1—C11	1.827 (2)	C34—H34	0.9500
P2—C51	1.827 (2)	C35—C36	1.395 (3)
P2—C61	1.828 (2)	C35—H35	0.9500
P2—C41	1.828 (2)	C36—H36	0.9500
O1—C3	1.442 (3)	C41—C42	1.395 (3)
O1—H1O	0.8576	C41—C46	1.398 (3)
O2—C5	1.397 (3)	C42—C43	1.394 (3)
O2—H2O	0.8400	C42—H42	0.9500
N1—C1	1.348 (3)	C43—C44	1.380 (4)
N1—C2	1.468 (3)	C43—H43	0.9500
N1—C4	1.476 (3)	C44—C45	1.382 (4)
C2—C3	1.513 (3)	C44—H44	0.9500
C2—H2A	0.9900	C45—C46	1.390 (3)
C2—H2B	0.9900	C45—H45	0.9500
C3—H3A	0.9900	C46—H46	0.9500
C3—H3B	0.9900	C51—C56	1.393 (3)
C4—C5	1.512 (3)	C51—C52	1.397 (3)
C4—H4A	0.9900	C52—C53	1.389 (3)
C4—H4B	0.9900	C52—H52	0.9500
C5—H5A	0.9900	C53—C54	1.391 (3)
C5—H5B	0.9900	C53—H53	0.9500
C11—C16	1.391 (3)	C54—C55	1.393 (3)
C11—C12	1.400 (3)	C54—H54	0.9500
C12—C13	1.391 (3)	C55—C56	1.394 (3)
C12—H12	0.9500	C55—H55	0.9500
C13—C14	1.391 (3)	C56—H56	0.9500
C13—H13	0.9500	C61—C62	1.393 (3)
C14—C15	1.386 (3)	C61—C66	1.398 (3)
C14—H14	0.9500	C62—C63	1.397 (3)
C15—C16	1.395 (3)	C62—H62	0.9500
C15—H15	0.9500	C63—C64	1.387 (3)
C16—H16	0.9500	C63—H63	0.9500
C21—C26	1.399 (3)	C64—C65	1.390 (4)
C21—C22	1.402 (3)	C64—H64	0.9500
C22—C23	1.386 (3)	C65—C66	1.389 (3)
C22—H22	0.9500	C65—H65	0.9500
C23—C24	1.394 (3)	C66—H66	0.9500
C23—H23	0.9500	C6—Cl2	1.733 (3)
C24—C25	1.386 (3)	C6—Cl1	1.748 (3)
C24—H24	0.9500	C6—Cl3	1.771 (3)
C25—C26	1.392 (3)	C6—H6	1.0000
C25—H25	0.9500
P2—Cu—P1	123.65 (2)	C24—C25—H25	120.0
P2—Cu—S1	109.81 (2)	C26—C25—H25	120.0
P1—Cu—S1	110.96 (2)	C25—C26—C21	120.80 (19)
P2—Cu—S2	123.17 (2)	C25—C26—H26	119.6
P1—Cu—S2	103.74 (2)	C21—C26—H26	119.6
S1—Cu—S2	75.264 (18)	C32—C31—C36	119.2 (2)
C1—S1—Cu	84.12 (7)	C32—C31—P1	122.25 (16)
C1—S2—Cu	82.75 (7)	C36—C31—P1	118.39 (16)
C31—P1—C21	101.95 (9)	C33—C32—C31	120.2 (2)
C31—P1—C11	101.78 (9)	C33—C32—H32	119.9
C21—P1—C11	104.44 (9)	C31—C32—H32	119.9
C31—P1—Cu	118.06 (7)	C34—C33—C32	120.3 (2)
C21—P1—Cu	114.57 (7)	C34—C33—H33	119.9
C11—P1—Cu	114.16 (7)	C32—C33—H33	119.9
C51—P2—C61	102.10 (9)	C33—C34—C35	120.0 (2)
C51—P2—C41	103.13 (9)	C33—C34—H34	120.0
C61—P2—C41	103.77 (9)	C35—C34—H34	120.0
C51—P2—Cu	117.50 (6)	C34—C35—C36	120.0 (2)
C61—P2—Cu	116.28 (7)	C34—C35—H35	120.0
C41—P2—Cu	112.27 (7)	C36—C35—H35	120.0
C3—O1—H1O	105.7	C31—C36—C35	120.2 (2)
C5—O2—H2O	109.4	C31—C36—H36	119.9
C1—N1—C2	120.12 (18)	C35—C36—H36	119.9
C1—N1—C4	119.48 (18)	C42—C41—C46	118.73 (19)
C2—N1—C4	120.09 (18)	C42—C41—P2	122.71 (17)
N1—C1—S1	120.50 (15)	C46—C41—P2	118.53 (16)
N1—C1—S2	122.12 (15)	C41—C42—C43	120.4 (2)
S1—C1—S2	117.38 (11)	C41—C42—H42	119.8
N1—C2—C3	113.01 (18)	C43—C42—H42	119.8
N1—C2—H2A	109.0	C44—C43—C42	120.3 (2)
C3—C2—H2A	109.0	C44—C43—H43	119.8
N1—C2—H2B	109.0	C42—C43—H43	119.8
C3—C2—H2B	109.0	C43—C44—C45	119.7 (2)
H2A—C2—H2B	107.8	C43—C44—H44	120.1
O1—C3—C2	108.3 (2)	C45—C44—H44	120.1
O1—C3—H3A	110.0	C44—C45—C46	120.5 (2)
C2—C3—H3A	110.0	C44—C45—H45	119.7
O1—C3—H3B	110.0	C46—C45—H45	119.7
C2—C3—H3B	110.0	C45—C46—C41	120.3 (2)
H3A—C3—H3B	108.4	C45—C46—H46	119.8
N1—C4—C5	114.9 (2)	C41—C46—H46	119.8
N1—C4—H4A	108.5	C56—C51—C52	119.51 (18)
C5—C4—H4A	108.5	C56—C51—P2	118.08 (15)
N1—C4—H4B	108.5	C52—C51—P2	122.29 (15)
C5—C4—H4B	108.5	C53—C52—C51	120.22 (19)
H4A—C4—H4B	107.5	C53—C52—H52	119.9
O2—C5—C4	111.6 (2)	C51—C52—H52	119.9
O2—C5—H5A	109.3	C52—C53—C54	120.1 (2)
C4—C5—H5A	109.3	C52—C53—H53	119.9
O2—C5—H5B	109.3	C54—C53—H53	119.9
C4—C5—H5B	109.3	C53—C54—C55	120.0 (2)
H5A—C5—H5B	108.0	C53—C54—H54	120.0
C16—C11—C12	119.11 (19)	C55—C54—H54	120.0
C16—C11—P1	124.41 (16)	C54—C55—C56	119.85 (19)
C12—C11—P1	116.47 (16)	C54—C55—H55	120.1
C13—C12—C11	120.4 (2)	C56—C55—H55	120.1
C13—C12—H12	119.8	C51—C56—C55	120.29 (19)
C11—C12—H12	119.8	C51—C56—H56	119.9
C14—C13—C12	120.2 (2)	C55—C56—H56	119.9
C14—C13—H13	119.9	C62—C61—C66	118.8 (2)
C12—C13—H13	119.9	C62—C61—P2	123.81 (16)
C15—C14—C13	119.6 (2)	C66—C61—P2	117.29 (16)
C15—C14—H14	120.2	C61—C62—C63	120.5 (2)
C13—C14—H14	120.2	C61—C62—H62	119.7
C14—C15—C16	120.4 (2)	C63—C62—H62	119.7
C14—C15—H15	119.8	C64—C63—C62	120.2 (2)
C16—C15—H15	119.8	C64—C63—H63	119.9
C11—C16—C15	120.3 (2)	C62—C63—H63	119.9
C11—C16—H16	119.9	C63—C64—C65	119.6 (2)
C15—C16—H16	119.9	C63—C64—H64	120.2
C26—C21—C22	118.63 (19)	C65—C64—H64	120.2
C26—C21—P1	122.28 (15)	C66—C65—C64	120.3 (2)
C22—C21—P1	118.91 (16)	C66—C65—H65	119.8
C23—C22—C21	120.4 (2)	C64—C65—H65	119.8
C23—C22—H22	119.8	C65—C66—C61	120.6 (2)
C21—C22—H22	119.8	C65—C66—H66	119.7
C22—C23—C24	120.4 (2)	C61—C66—H66	119.7
C22—C23—H23	119.8	Cl2—C6—Cl1	111.63 (17)
C24—C23—H23	119.8	Cl2—C6—Cl3	111.63 (17)
C25—C24—C23	119.7 (2)	Cl1—C6—Cl3	111.60 (15)
C25—C24—H24	120.1	Cl2—C6—H6	107.2
C23—C24—H24	120.1	Cl1—C6—H6	107.2
C24—C25—C26	120.0 (2)	Cl3—C6—H6	107.2
C2—N1—C1—S1	−179.88 (15)	P1—C31—C32—C33	−174.02 (18)
C4—N1—C1—S1	−6.2 (3)	C31—C32—C33—C34	0.3 (4)
C2—N1—C1—S2	0.1 (3)	C32—C33—C34—C35	−0.9 (4)
C4—N1—C1—S2	173.79 (16)	C33—C34—C35—C36	0.4 (4)
Cu—S1—C1—N1	−173.40 (17)	C32—C31—C36—C35	−1.3 (4)
Cu—S1—C1—S2	6.57 (10)	P1—C31—C36—C35	173.7 (2)
Cu—S2—C1—N1	173.49 (17)	C34—C35—C36—C31	0.7 (4)
Cu—S2—C1—S1	−6.48 (10)	C51—P2—C41—C42	96.01 (19)
C1—N1—C2—C3	−84.6 (2)	C61—P2—C41—C42	−10.2 (2)
C4—N1—C2—C3	101.8 (2)	Cu—P2—C41—C42	−136.55 (17)
N1—C2—C3—O1	−77.9 (2)	C51—P2—C41—C46	−85.86 (18)
C1—N1—C4—C5	83.8 (3)	C61—P2—C41—C46	167.95 (17)
C2—N1—C4—C5	−102.5 (2)	Cu—P2—C41—C46	41.58 (19)
N1—C4—C5—O2	82.1 (3)	C46—C41—C42—C43	−1.0 (3)
C31—P1—C11—C16	103.55 (19)	P2—C41—C42—C43	177.13 (18)
C21—P1—C11—C16	−2.2 (2)	C41—C42—C43—C44	−0.3 (4)
Cu—P1—C11—C16	−128.12 (17)	C42—C43—C44—C45	1.6 (4)
C31—P1—C11—C12	−75.31 (18)	C43—C44—C45—C46	−1.4 (4)
C21—P1—C11—C12	178.89 (16)	C44—C45—C46—C41	0.1 (4)
Cu—P1—C11—C12	53.01 (17)	C42—C41—C46—C45	1.1 (3)
C16—C11—C12—C13	0.2 (3)	P2—C41—C46—C45	−177.09 (19)
P1—C11—C12—C13	179.10 (17)	C61—P2—C51—C56	−94.07 (16)
C11—C12—C13—C14	0.0 (3)	C41—P2—C51—C56	158.48 (16)
C12—C13—C14—C15	−0.2 (4)	Cu—P2—C51—C56	34.40 (18)
C13—C14—C15—C16	0.2 (4)	C61—P2—C51—C52	82.03 (18)
C12—C11—C16—C15	−0.2 (3)	C41—P2—C51—C52	−25.42 (19)
P1—C11—C16—C15	−179.03 (18)	Cu—P2—C51—C52	−149.50 (15)
C14—C15—C16—C11	0.0 (4)	C56—C51—C52—C53	1.3 (3)
C31—P1—C21—C26	8.01 (19)	P2—C51—C52—C53	−174.71 (16)
C11—P1—C21—C26	113.67 (18)	C51—C52—C53—C54	−0.1 (3)
Cu—P1—C21—C26	−120.71 (16)	C52—C53—C54—C55	−0.6 (3)
C31—P1—C21—C22	−176.85 (16)	C53—C54—C55—C56	0.1 (3)
C11—P1—C21—C22	−71.19 (18)	C52—C51—C56—C55	−1.9 (3)
Cu—P1—C21—C22	54.43 (17)	P2—C51—C56—C55	174.34 (16)
C26—C21—C22—C23	−1.6 (3)	C54—C55—C56—C51	1.2 (3)
P1—C21—C22—C23	−176.94 (17)	C51—P2—C61—C62	−2.56 (19)
C21—C22—C23—C24	0.6 (3)	C41—P2—C61—C62	104.40 (18)
C22—C23—C24—C25	0.6 (3)	Cu—P2—C61—C62	−131.80 (16)
C23—C24—C25—C26	−0.9 (3)	C51—P2—C61—C66	173.12 (17)
C24—C25—C26—C21	−0.2 (3)	C41—P2—C61—C66	−79.91 (18)
C22—C21—C26—C25	1.4 (3)	Cu—P2—C61—C66	43.89 (18)
P1—C21—C26—C25	176.57 (16)	C66—C61—C62—C63	−0.3 (3)
C21—P1—C31—C32	79.67 (19)	P2—C61—C62—C63	175.35 (16)
C11—P1—C31—C32	−28.1 (2)	C61—C62—C63—C64	−0.4 (3)
Cu—P1—C31—C32	−153.85 (16)	C62—C63—C64—C65	0.9 (3)
C21—P1—C31—C36	−95.22 (19)	C63—C64—C65—C66	−0.7 (4)
C11—P1—C31—C36	157.05 (19)	C64—C65—C66—C61	0.0 (4)
Cu—P1—C31—C36	31.3 (2)	C62—C61—C66—C65	0.5 (3)
C36—C31—C32—C33	0.8 (3)	P2—C61—C66—C65	−175.44 (18)

Hydrogen-bond geometry (Å, º)

Cg1 is the ring centroid of (C51–C56).

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1	0.84	1.95	2.710 (3)	150
O1—H1O···O2^i	0.86	1.97	2.697 (3)	142
C6—Cl3···Cg1	1.77 (1)	3.81 (1)	3.798 (3)	76 (1)

Symmetry code: (i) −x, −y+2, −z+2.