Bis(tetra-n-propyl­ammonium) bis­(2-thioxo-1,3-dithiole-4,5-dithiol­ato-κ²S⁴,S⁵)copper(II)

The title compound, (C₁₂H₂₈N)₂[Cu(C₃S₅)₂], crystallizes with the Cu atom on an inversion centre. Each Cu atom is four-coordinated by four 2-thioxo-1,3-dithiole-4,5-dithiol­ate S atoms, forming a nearly square-planar arrangement.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.012 Å
• Disorder in main residue
• R factor = 0.079
• wR factor = 0.235
• Data-to-parameter ratio = 26.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......         10
PLAT301_ALERT_3_B Main Residue  Disorder .........................      29.00 Perc.

Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S4
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S5
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Cu1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         12
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          3
            S4  -CU1 -S4  -C2      7.00  0.00   3.666   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          4
            S5  -CU1 -S5  -C3     11.00  0.00   3.666   1.555   1.555   1.555
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         14
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      36.20 Deg.
              C13' -N1   -C13     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      36.10 Deg.
              C7   -N1   -C7'     1.555   1.555   1.555

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Bis(tetra-n-propylammonium) bis(2-thioxo-1,3-dithiole-4,5-dithiolato-κ²S⁴,S⁵)copper(II)

Crystal data

(C12H28N)2[Cu(C3S5)2]	F(000) = 878
Mr = 828.91	Dx = 1.312 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 4209 reflections
a = 8.106 (2) Å	θ = 2.6–27.1°
b = 20.401 (6) Å	µ = 1.04 mm^−1
c = 14.195 (4) Å	T = 298 K
β = 116.641 (4)°	Prism, red
V = 2098.2 (10) Å^3	0.48 × 0.30 × 0.26 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	4789 independent reflections
Radiation source: fine-focus sealed tube	3137 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
φ and ω scans	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −10→10
Tmin = 0.629, Tmax = 0.766	k = −26→26
12266 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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.235	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.1024P)^2 + 2.7561P] where P = (Fo^2 + 2Fc^2)/3
4789 reflections	(Δ/σ)max < 0.001
184 parameters	Δρmax = 0.97 e Å^−3
18 restraints	Δρmin = −0.75 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.5000	0.5000	0.5000	0.0612 (4)
S1	0.7167 (4)	0.68486 (14)	0.9722 (2)	0.0898 (8)
S2	0.7770 (3)	0.56983 (12)	0.86174 (17)	0.0777 (7)
S3	0.5009 (3)	0.66220 (13)	0.74366 (19)	0.0823 (7)
S4	0.7033 (4)	0.48458 (12)	0.67301 (18)	0.0835 (7)
S5	0.3917 (3)	0.59358 (14)	0.53715 (19)	0.0899 (7)
N1	0.7575 (7)	0.8758 (3)	0.7821 (4)	0.0553 (14)
C1	0.6688 (10)	0.6410 (4)	0.8652 (7)	0.0659 (19)
C2	0.6558 (10)	0.5536 (4)	0.7268 (6)	0.0606 (17)
C3	0.5282 (10)	0.5973 (4)	0.6715 (6)	0.0627 (18)
C4	0.740 (2)	0.8618 (7)	0.8838 (11)	0.064 (4)*	0.537 (9)
H4A	0.6210	0.8778	0.8750	0.077*	0.537 (9)
H4B	0.7418	0.8147	0.8940	0.077*	0.537 (9)
C5	0.887 (3)	0.8919 (11)	0.9798 (15)	0.085 (5)*	0.537 (9)
H5A	0.8638	0.9386	0.9798	0.102*	0.537 (9)
H5B	1.0051	0.8863	0.9789	0.102*	0.537 (9)
C6	0.896 (3)	0.8611 (11)	1.0805 (15)	0.089 (5)*	0.537 (9)
H6A	0.9927	0.8815	1.1410	0.134*	0.537 (9)
H6B	0.9204	0.8150	1.0811	0.134*	0.537 (9)
H6C	0.7802	0.8675	1.0825	0.134*	0.537 (9)
C4'	0.847 (2)	0.9072 (8)	0.8914 (13)	0.060 (4)*	0.463 (9)
H4'A	0.7811	0.9472	0.8899	0.072*	0.463 (9)
H4'B	0.9731	0.9188	0.9088	0.072*	0.463 (9)
C5'	0.846 (3)	0.8617 (10)	0.9779 (13)	0.071 (5)*	0.463 (9)
H5'A	0.7197	0.8518	0.9640	0.085*	0.463 (9)
H5'B	0.9081	0.8209	0.9793	0.085*	0.463 (9)
C6'	0.943 (3)	0.8964 (10)	1.0809 (13)	0.075 (5)*	0.463 (9)
H6'A	0.9428	0.8694	1.1362	0.112*	0.463 (9)
H6'B	0.8813	0.9370	1.0783	0.112*	0.463 (9)
H6'C	1.0683	0.9052	1.0945	0.112*	0.463 (9)
C7	0.752 (2)	0.9466 (5)	0.7603 (12)	0.065 (4)*	0.537 (9)
H7A	0.8586	0.9670	0.8165	0.078*	0.537 (9)
H7B	0.6428	0.9649	0.7621	0.078*	0.537 (9)
C8	0.749 (2)	0.9644 (8)	0.6580 (14)	0.076 (4)*	0.537 (9)
H8A	0.6423	0.9436	0.6020	0.091*	0.537 (9)
H8B	0.8579	0.9459	0.6565	0.091*	0.537 (9)
C9	0.7422 (16)	1.0383 (5)	0.6330 (9)	0.104 (3)	0.537 (9)
H9A	0.7424	1.0442	0.5659	0.157*	0.537 (9)
H9B	0.8482	1.0597	0.6868	0.157*	0.537 (9)
H9C	0.6320	1.0571	0.6308	0.157*	0.537 (9)
C7'	0.792 (2)	0.9292 (7)	0.7116 (12)	0.053 (3)*	0.463 (9)
H7'A	0.9232	0.9385	0.7430	0.063*	0.463 (9)
H7'B	0.7579	0.9103	0.6427	0.063*	0.463 (9)
C8'	0.692 (3)	0.9922 (9)	0.6970 (15)	0.078 (5)*	0.463 (9)
H8'A	0.7225	1.0115	0.7652	0.094*	0.463 (9)
H8'B	0.5600	0.9842	0.6619	0.094*	0.463 (9)
C9'	0.7422 (16)	1.0383 (5)	0.6330 (9)	0.104 (3)	0.463 (9)
H9'A	0.6766	1.0788	0.6245	0.157*	0.463 (9)
H9'B	0.7100	1.0194	0.5650	0.157*	0.463 (9)
H9'C	0.8726	1.0466	0.6682	0.157*	0.463 (9)
C10	0.6020 (19)	0.8355 (7)	0.6943 (11)	0.061 (3)*	0.537 (9)
H10A	0.6215	0.8366	0.6317	0.073*	0.537 (9)
H10B	0.6132	0.7902	0.7172	0.073*	0.537 (9)
C11	0.412 (3)	0.8578 (9)	0.6652 (17)	0.082 (5)*	0.537 (9)
H11A	0.3996	0.9037	0.6453	0.099*	0.537 (9)
H11B	0.3863	0.8536	0.7256	0.099*	0.537 (9)
C12	0.272 (3)	0.8176 (10)	0.5740 (15)	0.089 (5)*	0.537 (9)
H12A	0.1548	0.8393	0.5447	0.133*	0.537 (9)
H12B	0.2603	0.7750	0.5991	0.133*	0.537 (9)
H12C	0.3139	0.8130	0.5208	0.133*	0.537 (9)
C10'	0.553 (2)	0.8715 (8)	0.7449 (13)	0.062 (4)*	0.463 (9)
H10C	0.5086	0.9138	0.7554	0.075*	0.463 (9)
H10D	0.5287	0.8398	0.7882	0.075*	0.463 (9)
C11'	0.443 (3)	0.8520 (10)	0.6299 (17)	0.073 (5)*	0.463 (9)
H11C	0.4845	0.8095	0.6184	0.087*	0.463 (9)
H11D	0.4644	0.8836	0.5855	0.087*	0.463 (9)
C12'	0.2362 (17)	0.8490 (6)	0.5997 (10)	0.086 (6)*	0.463 (9)
H12D	0.1681	0.8400	0.5257	0.129*	0.463 (9)
H12E	0.1971	0.8903	0.6153	0.129*	0.463 (9)
H12F	0.2139	0.8149	0.6391	0.129*	0.463 (9)
C13	0.9373 (17)	0.8446 (6)	0.7915 (10)	0.062 (4)*	0.537 (9)
H13A	0.9347	0.8469	0.7226	0.075*	0.537 (9)
H13B	1.0389	0.8719	0.8384	0.075*	0.537 (9)
C14	0.981 (2)	0.7766 (9)	0.8287 (15)	0.084 (5)*	0.537 (9)
H14A	0.8735	0.7494	0.7908	0.101*	0.537 (9)
H14B	1.0115	0.7749	0.9029	0.101*	0.537 (9)
C15	1.1377 (18)	0.7497 (6)	0.8140 (11)	0.120 (4)	0.537 (9)
H15A	1.1597	0.7052	0.8383	0.180*	0.537 (9)
H15B	1.2462	0.7754	0.8536	0.180*	0.537 (9)
H15C	1.1086	0.7511	0.7406	0.180*	0.537 (9)
C13'	0.8432 (17)	0.8134 (6)	0.7753 (12)	0.056 (4)*	0.463 (9)
H13C	0.7891	0.8004	0.7018	0.068*	0.463 (9)
H13D	0.8099	0.7804	0.8128	0.068*	0.463 (9)
C14'	1.0481 (19)	0.8127 (10)	0.8169 (15)	0.074 (5)*	0.463 (9)
H14C	1.0806	0.8448	0.7777	0.089*	0.463 (9)
H14D	1.1016	0.8274	0.8896	0.089*	0.463 (9)
C15'	1.1377 (18)	0.7497 (6)	0.8140 (11)	0.120 (4)	0.463 (9)
H15D	1.2686	0.7561	0.8423	0.180*	0.463 (9)
H15E	1.0897	0.7348	0.7425	0.180*	0.463 (9)
H15F	1.1127	0.7176	0.8554	0.180*	0.463 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0445 (6)	0.0663 (7)	0.0623 (7)	0.0000 (5)	0.0146 (5)	0.0074 (5)
S1	0.1025 (19)	0.0955 (17)	0.0735 (15)	−0.0087 (14)	0.0412 (14)	−0.0078 (13)
S2	0.0773 (14)	0.0799 (14)	0.0583 (12)	0.0104 (11)	0.0149 (10)	0.0083 (10)
S3	0.0706 (13)	0.0874 (16)	0.0755 (14)	0.0200 (11)	0.0209 (11)	−0.0015 (12)
S4	0.0913 (12)	0.0677 (10)	0.0650 (11)	0.0207 (9)	0.0113 (9)	0.0078 (8)
S5	0.0660 (10)	0.1036 (12)	0.0688 (11)	0.0340 (9)	0.0021 (8)	−0.0010 (10)
N1	0.040 (3)	0.072 (4)	0.048 (3)	−0.007 (3)	0.014 (2)	−0.011 (3)
C1	0.053 (4)	0.070 (5)	0.075 (5)	−0.011 (3)	0.029 (4)	0.002 (4)
C2	0.055 (4)	0.064 (4)	0.055 (4)	0.000 (3)	0.018 (3)	0.009 (3)
C3	0.047 (4)	0.071 (5)	0.065 (4)	0.002 (3)	0.020 (3)	0.001 (4)
C9	0.099 (7)	0.078 (6)	0.122 (9)	0.018 (6)	0.037 (7)	0.018 (6)
C9'	0.099 (7)	0.078 (6)	0.122 (9)	0.018 (6)	0.037 (7)	0.018 (6)
C15	0.137 (10)	0.090 (7)	0.154 (12)	0.036 (7)	0.085 (10)	0.015 (8)
C15'	0.137 (10)	0.090 (7)	0.154 (12)	0.036 (7)	0.085 (10)	0.015 (8)

Geometric parameters (Å, º)

Cu1—S5	2.260 (2)	C8—H8A	0.9700
Cu1—S5^i	2.260 (2)	C8—H8B	0.9700
Cu1—S4	2.284 (2)	C9—H9A	0.9600
Cu1—S4^i	2.284 (2)	C9—H9B	0.9600
S1—C1	1.652 (9)	C9—H9C	0.9600
S2—C1	1.708 (9)	C7'—C8'	1.48 (2)
S2—C2	1.748 (8)	C7'—H7'A	0.9700
S3—C1	1.706 (9)	C7'—H7'B	0.9700
S3—C3	1.748 (8)	C8'—H8'A	0.9700
S4—C2	1.725 (8)	C8'—H8'B	0.9700
S5—C3	1.725 (8)	C10—C11	1.48 (2)
N1—C7	1.472 (10)	C10—H10A	0.9700
N1—C13'	1.474 (10)	C10—H10B	0.9700
N1—C10'	1.502 (17)	C11—C12	1.52 (3)
N1—C4'	1.528 (17)	C11—H11A	0.9700
N1—C13	1.541 (13)	C11—H11B	0.9700
N1—C4	1.541 (15)	C12—H12A	0.9600
N1—C10	1.552 (15)	C12—H12B	0.9600
N1—C7'	1.586 (16)	C12—H12C	0.9600
C2—C3	1.324 (10)	C10'—C11'	1.52 (3)
C4—C5	1.48 (3)	C10'—H10C	0.9700
C4—H4A	0.9700	C10'—H10D	0.9700
C4—H4B	0.9700	C11'—C12'	1.54 (2)
C5—C6	1.53 (3)	C11'—H11C	0.9700
C5—H5A	0.9700	C11'—H11D	0.9700
C5—H5B	0.9700	C12'—H12D	0.9600
C6—H6A	0.9600	C12'—H12E	0.9600
C6—H6B	0.9600	C12'—H12F	0.9600
C6—H6C	0.9600	C13—C14	1.47 (2)
C4'—C5'	1.54 (3)	C13—H13A	0.9700
C4'—H4'A	0.9700	C13—H13B	0.9700
C4'—H4'B	0.9700	C14—C15	1.478 (11)
C5'—C6'	1.493 (11)	C14—H14A	0.9700
C5'—H5'A	0.9700	C14—H14B	0.9700
C5'—H5'B	0.9700	C15—H15A	0.9600
C6'—H6'A	0.9600	C15—H15B	0.9600
C6'—H6'B	0.9600	C15—H15C	0.9600
C6'—H6'C	0.9600	C13'—C14'	1.493 (11)
C7—C8	1.49 (2)	C13'—H13C	0.9700
C7—H7A	0.9700	C13'—H13D	0.9700
C7—H7B	0.9700	C14'—H14C	0.9700
C8—C9	1.55 (2)	C14'—H14D	0.9700
S5—Cu1—S5^i	180.000 (1)	C8—C7—H7B	108.4
S5—Cu1—S4	91.95 (8)	H7A—C7—H7B	107.5
S5^i—Cu1—S4	88.05 (8)	C7—C8—C9	116.5 (13)
S5—Cu1—S4^i	88.05 (8)	C7—C8—H8A	108.2
S5^i—Cu1—S4^i	91.95 (8)	C9—C8—H8A	108.2
S4—Cu1—S4^i	180.0	C7—C8—H8B	108.2
C1—S2—C2	98.6 (4)	C9—C8—H8B	108.2
C1—S3—C3	98.4 (4)	H8A—C8—H8B	107.3
C2—S4—Cu1	99.6 (3)	C8—C9—H9A	109.5
C3—S5—Cu1	99.8 (3)	C8—C9—H9B	109.5
C7—N1—C13'	143.5 (10)	H9A—C9—H9B	109.5
C7—N1—C10'	93.3 (9)	C8—C9—H9C	109.5
C13'—N1—C10'	113.9 (9)	H9A—C9—H9C	109.5
C7—N1—C4'	76.1 (9)	H9B—C9—H9C	109.5
C13'—N1—C4'	114.0 (9)	C8'—C7'—N1	116.3 (11)
C10'—N1—C4'	109.0 (9)	C8'—C7'—H7'A	108.2
C7—N1—C13	111.3 (8)	N1—C7'—H7'A	108.2
C13'—N1—C13	36.2 (6)	C8'—C7'—H7'B	108.2
C10'—N1—C13	149.3 (9)	N1—C7'—H7'B	108.2
C4'—N1—C13	95.0 (8)	H7'A—C7'—H7'B	107.4
C7—N1—C4	111.8 (9)	C7'—C8'—H8'A	109.5
C13'—N1—C4	98.4 (9)	C7'—C8'—H8'B	109.5
C10'—N1—C4	76.4 (9)	H8'A—C8'—H8'B	108.1
C4'—N1—C4	47.7 (8)	C11—C10—N1	115.5 (12)
C13—N1—C4	108.9 (8)	C11—C10—H10A	108.4
C7—N1—C10	114.4 (9)	N1—C10—H10A	108.4
C13'—N1—C10	74.1 (8)	C11—C10—H10B	108.4
C10'—N1—C10	46.8 (8)	N1—C10—H10B	108.4
C4'—N1—C10	151.8 (9)	H10A—C10—H10B	107.5
C13—N1—C10	104.3 (8)	C10—C11—C12	110.8 (16)
C4—N1—C10	105.7 (8)	C10—C11—H11A	109.5
C7—N1—C7'	36.1 (7)	C12—C11—H11A	109.5
C13'—N1—C7'	109.3 (9)	C10—C11—H11B	109.5
C10'—N1—C7'	107.3 (9)	C12—C11—H11B	109.5
C4'—N1—C7'	102.5 (9)	H11A—C11—H11B	108.1
C13—N1—C7'	84.9 (8)	C11—C12—H12A	109.5
C4—N1—C7'	146.7 (9)	C11—C12—H12B	109.5
C10—N1—C7'	99.6 (8)	H12A—C12—H12B	109.5
S1—C1—S3	123.0 (5)	C11—C12—H12C	109.5
S1—C1—S2	125.1 (5)	H12A—C12—H12C	109.5
S3—C1—S2	111.9 (5)	H12B—C12—H12C	109.5
C3—C2—S4	123.9 (6)	N1—C10'—C11'	114.4 (14)
C3—C2—S2	115.3 (6)	N1—C10'—H10C	108.7
S4—C2—S2	120.8 (4)	C11'—C10'—H10C	108.7
C2—C3—S5	124.7 (6)	N1—C10'—H10D	108.7
C2—C3—S3	115.7 (6)	C11'—C10'—H10D	108.7
S5—C3—S3	119.6 (4)	H10C—C10'—H10D	107.6
C5—C4—N1	114.1 (12)	C10'—C11'—C12'	110.4 (16)
C5—C4—H4A	108.7	C10'—C11'—H11C	109.6
N1—C4—H4A	108.7	C12'—C11'—H11C	109.6
C5—C4—H4B	108.7	C10'—C11'—H11D	109.6
N1—C4—H4B	108.7	C12'—C11'—H11D	109.6
H4A—C4—H4B	107.6	H11C—C11'—H11D	108.1
C4—C5—C6	111.6 (18)	C11'—C12'—H12D	109.5
C4—C5—H5A	109.3	C11'—C12'—H12E	109.5
C6—C5—H5A	109.3	H12D—C12'—H12E	109.5
C4—C5—H5B	109.3	C11'—C12'—H12F	109.5
C6—C5—H5B	109.3	H12D—C12'—H12F	109.5
H5A—C5—H5B	108.0	H12E—C12'—H12F	109.5
C5—C6—H6A	109.5	C14—C13—N1	119.3 (10)
C5—C6—H6B	109.5	C14—C13—H13A	107.5
H6A—C6—H6B	109.5	N1—C13—H13A	107.5
C5—C6—H6C	109.5	C14—C13—H13B	107.5
H6A—C6—H6C	109.5	N1—C13—H13B	107.5
H6B—C6—H6C	109.5	H13A—C13—H13B	107.0
N1—C4'—C5'	112.8 (12)	C13—C14—C15	112.7 (13)
N1—C4'—H4'A	109.0	C13—C14—H14A	109.1
C5'—C4'—H4'A	109.0	C15—C14—H14A	109.1
N1—C4'—H4'B	109.0	C13—C14—H14B	109.1
C5'—C4'—H4'B	109.0	C15—C14—H14B	109.1
H4'A—C4'—H4'B	107.8	H14A—C14—H14B	107.8
C6'—C5'—C4'	107.7 (17)	C14—C15—H15A	109.5
C6'—C5'—H5'A	110.2	C14—C15—H15B	109.5
C4'—C5'—H5'A	110.2	H15A—C15—H15B	109.5
C6'—C5'—H5'B	110.2	C14—C15—H15C	109.5
C4'—C5'—H5'B	110.2	H15A—C15—H15C	109.5
H5'A—C5'—H5'B	108.5	H15B—C15—H15C	109.5
C5'—C6'—H6'A	109.5	N1—C13'—C14'	117.1 (12)
C5'—C6'—H6'B	109.5	N1—C13'—H13C	108.0
H6'A—C6'—H6'B	109.5	C14'—C13'—H13C	108.0
C5'—C6'—H6'C	109.5	N1—C13'—H13D	108.0
H6'A—C6'—H6'C	109.5	C14'—C13'—H13D	108.0
H6'B—C6'—H6'C	109.5	H13C—C13'—H13D	107.3
N1—C7—C8	115.5 (12)	C13'—C14'—H14C	107.8
N1—C7—H7A	108.4	C13'—C14'—H14D	107.8
C8—C7—H7A	108.4	H14C—C14'—H14D	107.2
N1—C7—H7B	108.4
S5—Cu1—S4—C2	−1.1 (3)	C4—N1—C7—C8	−174.1 (12)
S5^i—Cu1—S4—C2	178.9 (3)	C10—N1—C7—C8	−54.0 (16)
S4^i—Cu1—S4—C2	71 (100)	C7'—N1—C7—C8	17.9 (13)
S5^i—Cu1—S5—C3	−114 (100)	N1—C7—C8—C9	179.8 (11)
S4—Cu1—S5—C3	0.7 (3)	C7—N1—C7'—C8'	−23.6 (15)
S4^i—Cu1—S5—C3	−179.3 (3)	C13'—N1—C7'—C8'	171.4 (14)
C3—S3—C1—S1	179.3 (5)	C10'—N1—C7'—C8'	47.4 (16)
C3—S3—C1—S2	−1.1 (5)	C4'—N1—C7'—C8'	−67.4 (16)
C2—S2—C1—S1	−179.9 (5)	C13—N1—C7'—C8'	−161.4 (15)
C2—S2—C1—S3	0.6 (5)	C4—N1—C7'—C8'	−44 (2)
Cu1—S4—C2—C3	1.6 (7)	C10—N1—C7'—C8'	95.0 (15)
Cu1—S4—C2—S2	−178.7 (4)	C7—N1—C10—C11	−55.2 (16)
C1—S2—C2—C3	0.4 (7)	C13'—N1—C10—C11	162.7 (15)
C1—S2—C2—S4	−179.3 (5)	C10'—N1—C10—C11	15.0 (14)
S4—C2—C3—S5	−1.2 (11)	C4'—N1—C10—C11	51 (3)
S2—C2—C3—S5	179.0 (4)	C13—N1—C10—C11	−177.0 (13)
S4—C2—C3—S3	178.5 (4)	C4—N1—C10—C11	68.2 (15)
S2—C2—C3—S3	−1.3 (8)	C7'—N1—C10—C11	−89.9 (14)
Cu1—S5—C3—C2	0.0 (7)	N1—C10—C11—C12	176.3 (13)
Cu1—S5—C3—S3	−179.7 (4)	C7—N1—C10'—C11'	93.7 (15)
C1—S3—C3—C2	1.5 (7)	C13'—N1—C10'—C11'	−61.3 (16)
C1—S3—C3—S5	−178.8 (5)	C4'—N1—C10'—C11'	170.1 (14)
C7—N1—C4—C5	−59.6 (16)	C13—N1—C10'—C11'	−50 (2)
C13'—N1—C4—C5	99.6 (14)	C4—N1—C10'—C11'	−154.6 (15)
C10'—N1—C4—C5	−147.7 (15)	C10—N1—C10'—C11'	−27.2 (13)
C4'—N1—C4—C5	−15.3 (13)	C7'—N1—C10'—C11'	59.8 (16)
C13—N1—C4—C5	63.9 (15)	N1—C10'—C11'—C12'	−180.0 (12)
C10—N1—C4—C5	175.4 (13)	C7—N1—C13—C14	170.9 (13)
C7'—N1—C4—C5	−47 (2)	C13'—N1—C13—C14	−30.9 (14)
N1—C4—C5—C6	−163.6 (13)	C10'—N1—C13—C14	−48 (2)
C7—N1—C4'—C5'	159.8 (15)	C4'—N1—C13—C14	93.9 (14)
C13'—N1—C4'—C5'	−57.4 (16)	C4—N1—C13—C14	47.1 (14)
C10'—N1—C4'—C5'	71.2 (15)	C10—N1—C13—C14	−65.3 (14)
C13—N1—C4'—C5'	−89.4 (13)	C7'—N1—C13—C14	−164.0 (13)
C4—N1—C4'—C5'	21.7 (12)	N1—C13—C14—C15	169.0 (12)
C10—N1—C4'—C5'	44 (3)	C7—N1—C13'—C14'	49 (2)
C7'—N1—C4'—C5'	−175.3 (13)	C10'—N1—C13'—C14'	−176.3 (14)
N1—C4'—C5'—C6'	177.5 (14)	C4'—N1—C13'—C14'	−50.3 (17)
C13'—N1—C7—C8	42 (2)	C13—N1—C13'—C14'	13.2 (12)
C10'—N1—C7—C8	−97.4 (14)	C4—N1—C13'—C14'	−97.5 (15)
C4'—N1—C7—C8	153.8 (15)	C10—N1—C13'—C14'	158.5 (16)
C13—N1—C7—C8	63.9 (15)	C7'—N1—C13'—C14'	63.6 (16)

Symmetry code: (i) −x+1, −y+1, −z+1.