Bis[4-fluoro-N-(quinolin-8-yl)benzene­sulfonamidato-κ²N,N′]copper(II) dichloro­methane hemisolvate

In the title compound, [Cu(C₃₀H₂₀F₂N₄O₄S₂)]·0.5CH₂Cl₂, the Cu^II atom is four-coordinated by the N atoms of quinoline and sulfonamide groups in a distorted tetra­hedral geometry. The solvent mol­ecule lies on a twofold axis. Inter­molecular C—H...O hydrogen bonds link the mol­ecules into a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.009 Å
• Disorder in main residue
• R factor = 0.065
• wR factor = 0.201
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for       C27B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for       C28B
PLAT432_ALERT_2_B Short Inter X...Y Contact  C23    ..  F2B     ..       2.75 Ang.

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct...          1
PLAT213_ALERT_2_C Atom C29B    has ADP max/min Ratio .............       3.80 prolat
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.22 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C27A
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C29A
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C29B
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C30B
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         S2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C25
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C28A
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.20
PLAT301_ALERT_3_C Main Residue  Disorder .........................      12.00 Perc.
PLAT334_ALERT_2_C Small Average Benzene C-C Dist.  C10    -C15           1.36 Ang.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT431_ALERT_2_C Short Inter HL..A Contact  F2A    ..  N4      ..       2.91 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  F2A    ..  C23     ..       2.93 Ang.
PLAT731_ALERT_1_C Bond    Calc     1.34(2), Rep    1.339(8) ......       2.50 su-Rat
              F1   -C13     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc   1.392(17), Rep    1.394(8) ......       2.12 su-Rat
              C14  -C15     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.96(4), Rep   0.961(18) ......       2.22 su-Rat
              C31  -H31     1.555   1.555
PLAT732_ALERT_1_C Angle   Calc   122.0(15), Rep    122.1(7) ......       2.14 su-Rat
              C14  -C13  -C12     1.555   1.555   1.555

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

   7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  18 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Bis[4-fluoro-N-(quinolin-8-yl)benzenesulfonamidato-κ²N,N']copper(II) dichloromethane hemisolvate

Crystal data

[Cu(C30H20F2N4O4S2)]·0.5CH2Cl2	F(000) = 2880
Mr = 708.62	Dx = 1.555 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5953 reflections
a = 32.228 (3) Å	θ = 2.2–23.4°
b = 10.405 (1) Å	µ = 1.00 mm^−1
c = 23.817 (2) Å	T = 299 K
β = 130.70 (1)°	Prism, black
V = 6054.9 (13) Å^3	0.40 × 0.30 × 0.30 mm
Z = 8

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	6074 independent reflections
Radiation source: fine-focus sealed tube	4591 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
ω and φ scans	θmax = 26.4°, θmin = 4.1°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2004)	h = −30→40
Tmin = 0.690, Tmax = 0.753	k = −12→12
20303 measured reflections	l = −29→23

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.201	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.1168P)^2 + 6.3418P] where P = (Fo^2 + 2Fc^2)/3
6074 reflections	(Δ/σ)max = 0.028
460 parameters	Δρmax = 1.16 e Å^−3
19 restraints	Δρmin = −0.73 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	Occ. (<1)
Cu1	0.130653 (18)	0.36706 (4)	0.01543 (3)	0.0524 (2)
S1	0.21553 (4)	0.37014 (12)	0.18383 (6)	0.0672 (3)
S2	0.05294 (4)	0.14269 (9)	−0.07874 (6)	0.0580 (3)
F1	0.1132 (3)	0.1651 (6)	0.2961 (4)	0.210 (3)
F2A	0.1450 (8)	−0.3606 (6)	−0.0342 (15)	0.185 (8)	0.69 (3)
F2B	0.1884 (17)	−0.328 (2)	0.038 (2)	0.168 (12)	0.31 (3)
O1	0.22781 (14)	0.2609 (3)	0.1596 (2)	0.0856 (10)
O2	0.25962 (12)	0.4501 (5)	0.2410 (2)	0.1038 (13)
O3	0.04843 (14)	0.1678 (3)	−0.0239 (2)	0.0772 (9)
O4	0.00326 (14)	0.1436 (4)	−0.1535 (2)	0.0999 (13)
N1	0.16965 (12)	0.4477 (3)	0.11050 (17)	0.0599 (8)
N2	0.06931 (11)	0.4779 (3)	−0.01070 (16)	0.0490 (7)
N3	0.09527 (14)	0.2462 (3)	−0.0649 (2)	0.0589 (8)
N4	0.18474 (12)	0.3753 (3)	−0.00018 (18)	0.0514 (7)
C1	0.14316 (14)	0.5550 (4)	0.1096 (2)	0.0526 (8)
C2	0.16416 (18)	0.6462 (4)	0.1643 (2)	0.0675 (11)
H2	0.2000	0.6388	0.2087	0.081*
C3	0.13143 (18)	0.7505 (5)	0.1528 (3)	0.0711 (12)
H3	0.1461	0.8112	0.1901	0.085*
C4	0.07870 (17)	0.7644 (4)	0.0882 (2)	0.0632 (10)
H4	0.0580	0.8341	0.0821	0.076*
C5	0.05557 (15)	0.6736 (4)	0.0309 (2)	0.0520 (8)
C6	0.00169 (16)	0.6780 (4)	−0.0366 (2)	0.0597 (9)
H6	−0.0212	0.7451	−0.0463	0.072*
C7	−0.01719 (16)	0.5841 (4)	−0.0881 (2)	0.0650 (10)
H7	−0.0531	0.5862	−0.1326	0.078*
C8	0.01780 (15)	0.4845 (4)	−0.0737 (2)	0.0593 (9)
H8	0.0046	0.4211	−0.1093	0.071*
C9	0.08832 (14)	0.5698 (3)	0.04189 (19)	0.0465 (7)
C10	0.18406 (19)	0.3096 (5)	0.2180 (2)	0.0692 (11)
C11	0.1911 (3)	0.3691 (7)	0.2746 (4)	0.111 (2)
H11	0.2124	0.4429	0.2961	0.134*
C12	0.1659 (4)	0.3181 (11)	0.2999 (5)	0.140 (3)
H12	0.1700	0.3581	0.3382	0.167*
C13	0.1357 (5)	0.2114 (8)	0.2689 (6)	0.137 (3)
C14	0.1272 (4)	0.1536 (6)	0.2124 (5)	0.116 (2)
H14	0.1047	0.0816	0.1902	0.140*
C15	0.1526 (3)	0.2032 (6)	0.1872 (4)	0.0980 (18)
H15	0.1478	0.1625	0.1485	0.118*
C16	0.11625 (16)	0.2449 (3)	−0.1013 (2)	0.0548 (9)
C17	0.09495 (19)	0.1832 (5)	−0.1662 (3)	0.0683 (11)
H17	0.0634	0.1337	−0.1908	0.082*
C18	0.1214 (2)	0.1956 (5)	−0.1954 (3)	0.0779 (13)
H18	0.1067	0.1530	−0.2391	0.094*
C19	0.16690 (19)	0.2666 (5)	−0.1623 (3)	0.0754 (13)
H19	0.1825	0.2745	−0.1841	0.090*
C20	0.19109 (17)	0.3294 (4)	−0.0944 (2)	0.0620 (10)
C21	0.23915 (17)	0.4034 (5)	−0.0537 (3)	0.0679 (11)
H21	0.2575	0.4144	−0.0713	0.081*
C22	0.25869 (18)	0.4584 (5)	0.0104 (3)	0.0720 (12)
H22	0.2907	0.5065	0.0374	0.086*
C23	0.23070 (16)	0.4432 (4)	0.0369 (2)	0.0610 (9)
H23	0.2447	0.4815	0.0815	0.073*
C24	0.16464 (15)	0.3179 (4)	−0.0649 (2)	0.0528 (8)
C25	0.0840 (2)	−0.0086 (4)	−0.0597 (3)	0.0651 (11)
C26A	0.1321 (4)	−0.0399 (16)	0.0086 (6)	0.085 (5)	0.69 (3)
H26A	0.1500	0.0187	0.0475	0.102*	0.69 (3)
C27A	0.1533 (6)	−0.1600 (17)	0.0182 (13)	0.120 (8)	0.69 (3)
H27A	0.1861	−0.1845	0.0639	0.144*	0.69 (3)
C28A	0.1255 (10)	−0.2433 (12)	−0.0404 (15)	0.116 (9)	0.69 (3)
C29A	0.0768 (9)	−0.2137 (10)	−0.1105 (13)	0.120 (6)	0.69 (3)
H29A	0.0601	−0.2716	−0.1496	0.144*	0.69 (3)
C30A	0.0538 (6)	−0.0912 (11)	−0.1198 (7)	0.083 (3)	0.69 (3)
H30A	0.0200	−0.0673	−0.1643	0.099*	0.69 (3)
C26B	0.1262 (8)	−0.018 (4)	0.0144 (11)	0.096 (12)	0.31 (3)
H26B	0.1307	0.0503	0.0429	0.116*	0.31 (3)
C27B	0.1632 (16)	−0.117 (3)	0.053 (2)	0.144 (18)	0.31 (3)
H27B	0.1888	−0.1172	0.1042	0.173*	0.31 (3)
C28B	0.1610 (16)	−0.215 (2)	0.012 (2)	0.107 (10)	0.31 (3)
C29B	0.116 (2)	−0.214 (3)	−0.062 (2)	0.126 (17)	0.31 (3)
H29B	0.1095	−0.2856	−0.0901	0.151*	0.31 (3)
C30B	0.0781 (16)	−0.111 (2)	−0.1001 (19)	0.114 (12)	0.31 (3)
H30B	0.0499	−0.1140	−0.1512	0.137*	0.31 (3)
Cl1	0.05397 (9)	0.4840 (2)	0.27079 (12)	0.1410 (7)
C31	0.0000	0.5756 (9)	0.2500	0.112 (3)
H31	0.012 (3)	0.626 (3)	0.2921 (15)	0.135*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0538 (3)	0.0558 (3)	0.0619 (3)	0.01222 (18)	0.0441 (3)	0.00342 (18)
S1	0.0471 (5)	0.0933 (8)	0.0583 (6)	0.0228 (5)	0.0331 (5)	0.0159 (5)
S2	0.0522 (5)	0.0605 (6)	0.0737 (7)	0.0042 (4)	0.0465 (5)	−0.0008 (4)
F1	0.346 (9)	0.189 (5)	0.295 (8)	0.023 (5)	0.298 (8)	0.042 (5)
F2A	0.273 (16)	0.063 (4)	0.36 (2)	0.064 (6)	0.268 (19)	0.054 (6)
F2B	0.24 (3)	0.100 (11)	0.24 (3)	0.099 (15)	0.19 (3)	0.066 (15)
O1	0.084 (2)	0.108 (2)	0.093 (2)	0.0515 (19)	0.070 (2)	0.0375 (19)
O2	0.0445 (16)	0.139 (3)	0.081 (2)	0.0086 (18)	0.0199 (17)	0.014 (2)
O3	0.091 (2)	0.0737 (18)	0.117 (3)	0.0033 (16)	0.090 (2)	−0.0042 (18)
O4	0.0558 (19)	0.128 (3)	0.088 (3)	−0.0003 (18)	0.0348 (19)	0.010 (2)
N1	0.0503 (17)	0.077 (2)	0.0563 (18)	0.0217 (15)	0.0362 (15)	0.0086 (15)
N2	0.0488 (15)	0.0560 (16)	0.0471 (15)	0.0089 (13)	0.0335 (13)	−0.0009 (12)
N3	0.070 (2)	0.0567 (17)	0.079 (2)	−0.0010 (15)	0.0618 (19)	−0.0063 (15)
N4	0.0520 (17)	0.0507 (16)	0.0628 (19)	0.0134 (13)	0.0423 (16)	0.0106 (13)
C1	0.0431 (17)	0.070 (2)	0.051 (2)	0.0053 (16)	0.0333 (16)	−0.0003 (16)
C2	0.054 (2)	0.086 (3)	0.056 (2)	−0.0020 (19)	0.033 (2)	−0.012 (2)
C3	0.065 (2)	0.084 (3)	0.072 (3)	−0.009 (2)	0.048 (2)	−0.027 (2)
C4	0.063 (2)	0.064 (2)	0.078 (3)	0.0031 (18)	0.052 (2)	−0.0134 (19)
C5	0.0535 (19)	0.0562 (19)	0.064 (2)	0.0063 (16)	0.0460 (19)	−0.0012 (16)
C6	0.056 (2)	0.065 (2)	0.066 (2)	0.0210 (18)	0.043 (2)	0.0067 (18)
C7	0.046 (2)	0.087 (3)	0.057 (2)	0.0176 (19)	0.0313 (18)	0.006 (2)
C8	0.057 (2)	0.068 (2)	0.055 (2)	0.0051 (17)	0.0372 (19)	−0.0089 (17)
C9	0.0468 (17)	0.0554 (19)	0.0503 (18)	0.0051 (14)	0.0373 (16)	0.0017 (15)
C10	0.068 (3)	0.086 (3)	0.059 (2)	0.026 (2)	0.044 (2)	0.015 (2)
C11	0.132 (5)	0.137 (6)	0.082 (4)	−0.006 (4)	0.078 (4)	−0.010 (3)
C12	0.185 (8)	0.181 (8)	0.111 (5)	0.011 (7)	0.123 (6)	0.003 (6)
C13	0.225 (10)	0.115 (6)	0.188 (8)	0.042 (6)	0.186 (9)	0.043 (6)
C14	0.165 (7)	0.088 (4)	0.159 (7)	0.011 (4)	0.134 (6)	0.013 (4)
C15	0.144 (5)	0.090 (4)	0.117 (4)	0.024 (4)	0.111 (5)	0.007 (3)
C16	0.061 (2)	0.0516 (19)	0.072 (2)	0.0133 (16)	0.053 (2)	0.0055 (17)
C17	0.070 (3)	0.080 (3)	0.070 (3)	0.005 (2)	0.052 (2)	−0.003 (2)
C18	0.083 (3)	0.100 (4)	0.073 (3)	0.008 (3)	0.060 (3)	−0.005 (3)
C19	0.070 (3)	0.111 (4)	0.069 (3)	0.019 (3)	0.056 (2)	0.014 (2)
C20	0.062 (2)	0.073 (2)	0.072 (3)	0.0193 (19)	0.053 (2)	0.017 (2)
C21	0.059 (2)	0.087 (3)	0.078 (3)	0.011 (2)	0.053 (2)	0.014 (2)
C22	0.056 (2)	0.079 (3)	0.088 (3)	0.007 (2)	0.050 (2)	0.012 (2)
C23	0.057 (2)	0.059 (2)	0.070 (2)	0.0069 (17)	0.043 (2)	0.0031 (18)
C24	0.056 (2)	0.0542 (19)	0.061 (2)	0.0171 (16)	0.0435 (18)	0.0126 (16)
C25	0.080 (3)	0.057 (2)	0.093 (3)	0.004 (2)	0.071 (3)	0.003 (2)
C26A	0.058 (5)	0.094 (11)	0.119 (8)	0.031 (5)	0.064 (6)	0.030 (6)
C27A	0.126 (10)	0.084 (11)	0.22 (2)	0.060 (9)	0.146 (14)	0.072 (13)
C28A	0.162 (16)	0.061 (6)	0.22 (2)	0.060 (9)	0.169 (19)	0.073 (10)
C29A	0.225 (18)	0.054 (5)	0.172 (15)	−0.007 (7)	0.170 (16)	−0.018 (7)
C30A	0.129 (9)	0.047 (5)	0.118 (7)	0.006 (5)	0.101 (7)	−0.011 (5)
C26B	0.095 (19)	0.068 (12)	0.19 (3)	0.041 (11)	0.12 (2)	0.050 (14)
C27B	0.24 (4)	0.09 (2)	0.26 (4)	0.05 (2)	0.23 (4)	0.05 (2)
C28B	0.12 (2)	0.078 (18)	0.17 (3)	0.021 (15)	0.12 (2)	0.005 (18)
C29B	0.25 (4)	0.069 (16)	0.11 (2)	0.08 (2)	0.14 (3)	0.024 (16)
C30B	0.18 (3)	0.063 (14)	0.18 (3)	0.042 (16)	0.15 (3)	0.009 (15)
Cl1	0.1446 (16)	0.1107 (13)	0.1295 (15)	0.0296 (11)	0.0724 (14)	0.0136 (11)
C31	0.139 (8)	0.096 (6)	0.113 (7)	0.000	0.087 (7)	0.000

Geometric parameters (Å, º)

Cu1—N3	1.923 (3)	C13—C14	1.327 (11)
Cu1—N1	1.923 (3)	C14—C15	1.394 (8)
Cu1—N2	2.005 (3)	C14—H14	0.93
Cu1—N4	2.007 (3)	C15—H15	0.93
S1—O2	1.429 (4)	C16—C17	1.376 (6)
S1—O1	1.442 (3)	C16—C24	1.413 (6)
S1—N1	1.587 (3)	C17—C18	1.412 (6)
S1—C10	1.779 (5)	C17—H17	0.93
S2—O4	1.419 (4)	C18—C19	1.346 (7)
S2—O3	1.429 (3)	C18—H18	0.93
S2—N3	1.595 (3)	C19—C20	1.417 (7)
S2—C25	1.759 (4)	C19—H19	0.93
F1—C13	1.339 (8)	C20—C21	1.405 (6)
F2A—C28A	1.337 (12)	C20—C24	1.419 (5)
F2B—C28B	1.353 (17)	C21—C22	1.342 (7)
N1—C1	1.397 (5)	C21—H21	0.93
N2—C8	1.328 (5)	C22—C23	1.407 (6)
N2—C9	1.363 (5)	C22—H22	0.93
N3—C16	1.403 (5)	C23—H23	0.93
N4—C23	1.329 (5)	C25—C26B	1.359 (18)
N4—C24	1.360 (5)	C25—C30B	1.367 (17)
C1—C2	1.379 (6)	C25—C26A	1.367 (10)
C1—C9	1.425 (5)	C25—C30A	1.385 (10)
C2—C3	1.411 (6)	C26A—C27A	1.370 (16)
C2—H2	0.93	C26A—H26A	0.93
C3—C4	1.366 (6)	C27A—C28A	1.369 (16)
C3—H3	0.93	C27A—H27A	0.93
C4—C5	1.409 (5)	C28A—C29A	1.388 (16)
C4—H4	0.93	C29A—C30A	1.418 (14)
C5—C6	1.400 (5)	C29A—H29A	0.93
C5—C9	1.410 (5)	C30A—H30A	0.93
C6—C7	1.363 (6)	C26B—C27B	1.37 (2)
C6—H6	0.93	C26B—H26B	0.93
C7—C8	1.399 (5)	C27B—C28B	1.37 (2)
C7—H7	0.93	C27B—H27B	0.93
C8—H8	0.93	C28B—C29B	1.39 (2)
C10—C15	1.349 (8)	C29B—C30B	1.41 (2)
C10—C11	1.361 (7)	C29B—H29B	0.93
C11—C12	1.394 (10)	C30B—H30B	0.93
C11—H11	0.93	Cl1—C31	1.748 (6)
C12—C13	1.336 (12)	C31—Cl1^i	1.748 (6)
C12—H12	0.93	C31—H31	0.961 (18)
N3—Cu1—N1	164.82 (15)	C15—C14—H14	120.7
N3—Cu1—N2	104.04 (13)	C10—C15—C14	120.9 (6)
N1—Cu1—N2	82.50 (12)	C10—C15—H15	119.6
N3—Cu1—N4	82.33 (13)	C14—C15—H15	119.6
N1—Cu1—N4	102.70 (13)	C17—C16—N3	127.6 (4)
N2—Cu1—N4	135.84 (12)	C17—C16—C24	118.8 (3)
O2—S1—O1	118.6 (2)	N3—C16—C24	113.6 (3)
O2—S1—N1	112.7 (2)	C16—C17—C18	119.4 (4)
O1—S1—N1	105.19 (19)	C16—C17—H17	120.3
O2—S1—C10	106.3 (2)	C18—C17—H17	120.3
O1—S1—C10	106.9 (2)	C19—C18—C17	122.7 (4)
N1—S1—C10	106.48 (18)	C19—C18—H18	118.7
O4—S2—O3	116.2 (2)	C17—C18—H18	118.7
O4—S2—N3	111.6 (2)	C18—C19—C20	119.9 (4)
O3—S2—N3	105.74 (18)	C18—C19—H19	120.0
O4—S2—C25	108.4 (3)	C20—C19—H19	120.0
O3—S2—C25	107.9 (2)	C21—C20—C19	125.3 (4)
N3—S2—C25	106.53 (18)	C21—C20—C24	117.0 (4)
C1—N1—S1	123.0 (3)	C19—C20—C24	117.7 (4)
C1—N1—Cu1	114.0 (2)	C22—C21—C20	120.4 (4)
S1—N1—Cu1	119.9 (2)	C22—C21—H21	119.8
C8—N2—C9	118.9 (3)	C20—C21—H21	119.8
C8—N2—Cu1	129.3 (2)	C21—C22—C23	120.0 (4)
C9—N2—Cu1	110.9 (2)	C21—C22—H22	120.0
C16—N3—S2	123.9 (3)	C23—C22—H22	120.0
C16—N3—Cu1	114.1 (3)	N4—C23—C22	121.6 (4)
S2—N3—Cu1	121.28 (18)	N4—C23—H23	119.2
C23—N4—C24	119.2 (3)	C22—C23—H23	119.2
C23—N4—Cu1	128.7 (3)	N4—C24—C16	116.7 (3)
C24—N4—Cu1	111.2 (2)	N4—C24—C20	121.9 (4)
C2—C1—N1	128.0 (3)	C16—C24—C20	121.4 (4)
C2—C1—C9	118.5 (3)	C26B—C25—C30B	115 (2)
N1—C1—C9	113.4 (3)	C26A—C25—C30A	124.7 (9)
C1—C2—C3	120.1 (4)	C26B—C25—S2	108.8 (18)
C1—C2—H2	119.9	C30B—C25—S2	136.5 (16)
C3—C2—H2	119.9	C26A—C25—S2	122.3 (8)
C4—C3—C2	121.6 (4)	C30A—C25—S2	113.0 (7)
C4—C3—H3	119.2	C27A—C26A—C25	118.1 (14)
C2—C3—H3	119.2	C27A—C26A—H26A	120.9
C3—C4—C5	120.2 (4)	C25—C26A—H26A	120.9
C3—C4—H4	119.9	C26A—C27A—C28A	118.9 (14)
C5—C4—H4	119.9	C26A—C27A—H27A	120.5
C6—C5—C4	124.5 (3)	C28A—C27A—H27A	120.5
C6—C5—C9	117.1 (3)	F2A—C28A—C27A	121.2 (17)
C4—C5—C9	118.3 (3)	F2A—C28A—C29A	114.6 (16)
C7—C6—C5	120.1 (3)	C27A—C28A—C29A	124.2 (11)
C7—C6—H6	119.9	C28A—C29A—C30A	116.9 (11)
C5—C6—H6	119.9	C28A—C29A—H29A	121.5
C6—C7—C8	119.6 (4)	C30A—C29A—H29A	121.5
C6—C7—H7	120.2	C25—C30A—C29A	117.0 (11)
C8—C7—H7	120.2	C25—C30A—H30A	121.5
N2—C8—C7	121.9 (4)	C29A—C30A—H30A	121.5
N2—C8—H8	119.0	C25—C26B—C27B	128 (4)
C7—C8—H8	119.0	C25—C26B—H26B	115.8
N2—C9—C5	122.2 (3)	C27B—C26B—H26B	115.9
N2—C9—C1	116.6 (3)	C28B—C27B—C26B	118 (4)
C5—C9—C1	121.2 (3)	C28B—C27B—H27B	121.2
C15—C10—C11	119.5 (5)	C26B—C27B—H27B	121.2
C15—C10—S1	119.4 (4)	F2B—C28B—C27B	127 (3)
C11—C10—S1	121.0 (5)	F2B—C28B—C29B	115 (2)
C10—C11—C12	119.1 (7)	C27B—C28B—C29B	115 (2)
C10—C11—H11	120.4	C28B—C29B—C30B	125 (2)
C12—C11—H11	120.4	C28B—C29B—H29B	117.4
C13—C12—C11	119.7 (7)	C30B—C29B—H29B	117.4
C13—C12—H12	120.1	C25—C30B—C29B	118 (2)
C11—C12—H12	120.1	C25—C30B—H30B	120.8
C14—C13—C12	122.1 (7)	C29B—C30B—H30B	120.8
C14—C13—F1	120.5 (10)	Cl1^i—C31—Cl1	114.0 (6)
C12—C13—F1	117.3 (8)	Cl1^i—C31—H31	105 (4)
C13—C14—C15	118.5 (8)	Cl1—C31—H31	110 (4)
C13—C14—H14	120.7
O2—S1—N1—C1	−55.1 (4)	C11—C12—C13—F1	178.8 (8)
O1—S1—N1—C1	174.3 (3)	C12—C13—C14—C15	2.9 (14)
C10—S1—N1—C1	61.0 (4)	F1—C13—C14—C15	−178.3 (8)
O2—S1—N1—Cu1	146.1 (2)	C11—C10—C15—C14	0.0 (9)
O1—S1—N1—Cu1	15.5 (3)	S1—C10—C15—C14	−179.7 (5)
C10—S1—N1—Cu1	−97.8 (3)	C13—C14—C15—C10	−1.7 (11)
N3—Cu1—N1—C1	−130.3 (5)	S2—N3—C16—C17	19.5 (6)
N2—Cu1—N1—C1	−13.6 (3)	Cu1—N3—C16—C17	−170.2 (4)
N4—Cu1—N1—C1	121.8 (3)	S2—N3—C16—C24	−161.1 (3)
N3—Cu1—N1—S1	30.4 (6)	Cu1—N3—C16—C24	9.2 (4)
N2—Cu1—N1—S1	147.1 (2)	N3—C16—C17—C18	178.5 (4)
N4—Cu1—N1—S1	−77.5 (2)	C24—C16—C17—C18	−0.9 (6)
N3—Cu1—N2—C8	−10.8 (4)	C16—C17—C18—C19	−0.4 (8)
N1—Cu1—N2—C8	−176.8 (4)	C17—C18—C19—C20	1.9 (8)
N4—Cu1—N2—C8	82.6 (4)	C18—C19—C20—C21	178.4 (5)
N3—Cu1—N2—C9	−179.9 (2)	C18—C19—C20—C24	−2.1 (7)
N1—Cu1—N2—C9	14.0 (2)	C19—C20—C21—C22	−179.7 (4)
N4—Cu1—N2—C9	−86.5 (3)	C24—C20—C21—C22	0.8 (6)
O4—S2—N3—C16	−60.9 (4)	C20—C21—C22—C23	−0.7 (7)
O3—S2—N3—C16	171.9 (3)	C24—N4—C23—C22	0.8 (5)
C25—S2—N3—C16	57.2 (4)	Cu1—N4—C23—C22	−167.3 (3)
O4—S2—N3—Cu1	129.4 (3)	C21—C22—C23—N4	−0.1 (6)
O3—S2—N3—Cu1	2.3 (3)	C23—N4—C24—C16	178.8 (3)
C25—S2—N3—Cu1	−112.4 (2)	Cu1—N4—C24—C16	−11.2 (4)
N1—Cu1—N3—C16	−122.4 (5)	C23—N4—C24—C20	−0.6 (5)
N2—Cu1—N3—C16	123.5 (3)	Cu1—N4—C24—C20	169.5 (3)
N4—Cu1—N3—C16	−11.9 (3)	C17—C16—C24—N4	−178.8 (4)
N1—Cu1—N3—S2	48.2 (6)	N3—C16—C24—N4	1.7 (5)
N2—Cu1—N3—S2	−65.9 (2)	C17—C16—C24—C20	0.6 (6)
N4—Cu1—N3—S2	158.7 (2)	N3—C16—C24—C20	−178.9 (3)
N3—Cu1—N4—C23	−178.6 (3)	C21—C20—C24—N4	−0.2 (5)
N1—Cu1—N4—C23	−13.1 (3)	C19—C20—C24—N4	−179.7 (4)
N2—Cu1—N4—C23	79.1 (4)	C21—C20—C24—C16	−179.6 (4)
N3—Cu1—N4—C24	12.6 (2)	C19—C20—C24—C16	0.9 (6)
N1—Cu1—N4—C24	178.0 (2)	O4—S2—C25—C26B	−169.4 (11)
N2—Cu1—N4—C24	−89.7 (3)	O3—S2—C25—C26B	−42.8 (11)
S1—N1—C1—C2	32.7 (6)	N3—S2—C25—C26B	70.3 (11)
Cu1—N1—C1—C2	−167.3 (4)	O4—S2—C25—C30B	15 (2)
S1—N1—C1—C9	−149.3 (3)	O3—S2—C25—C30B	141 (2)
Cu1—N1—C1—C9	10.7 (4)	N3—S2—C25—C30B	−105 (2)
N1—C1—C2—C3	178.5 (4)	O4—S2—C25—C26A	−178.6 (7)
C9—C1—C2—C3	0.6 (6)	O3—S2—C25—C26A	−52.0 (7)
C1—C2—C3—C4	0.0 (7)	N3—S2—C25—C26A	61.2 (7)
C2—C3—C4—C5	0.0 (7)	O4—S2—C25—C30A	−0.5 (7)
C3—C4—C5—C6	178.6 (4)	O3—S2—C25—C30A	126.1 (6)
C3—C4—C5—C9	−0.5 (6)	N3—S2—C25—C30A	−120.7 (6)
C4—C5—C6—C7	−178.8 (4)	C26B—C25—C26A—C27A	146 (7)
C9—C5—C6—C7	0.4 (6)	C30B—C25—C26A—C27A	−9.2 (18)
C5—C6—C7—C8	−1.0 (6)	C30A—C25—C26A—C27A	2.2 (11)
C9—N2—C8—C7	1.1 (6)	S2—C25—C26A—C27A	−179.9 (6)
Cu1—N2—C8—C7	−167.3 (3)	C25—C26A—C27A—C28A	−0.4 (12)
C6—C7—C8—N2	0.3 (7)	C26A—C27A—C28A—F2A	178.5 (9)
C8—N2—C9—C5	−1.7 (5)	C26A—C27A—C28A—C29A	1.0 (18)
Cu1—N2—C9—C5	168.6 (3)	F2A—C28A—C29A—C30A	179.1 (10)
C8—N2—C9—C1	177.4 (3)	C27A—C28A—C29A—C30A	−3 (2)
Cu1—N2—C9—C1	−12.2 (4)	C26B—C25—C30A—C29A	−18 (2)
C6—C5—C9—N2	1.0 (5)	C30B—C25—C30A—C29A	21 (4)
C4—C5—C9—N2	−179.8 (3)	C26A—C25—C30A—C29A	−4.5 (15)
C6—C5—C9—C1	−178.1 (3)	S2—C25—C30A—C29A	177.5 (9)
C4—C5—C9—C1	1.1 (5)	C28A—C29A—C30A—C25	4.7 (17)
C2—C1—C9—N2	179.7 (4)	C30B—C25—C26B—C27B	0.7 (19)
N1—C1—C9—N2	1.5 (5)	C26A—C25—C26B—C27B	−26 (6)
C2—C1—C9—C5	−1.1 (5)	C30A—C25—C26B—C27B	19 (2)
N1—C1—C9—C5	−179.3 (3)	S2—C25—C26B—C27B	−176.2 (10)
O2—S1—C10—C15	−160.1 (4)	C25—C26B—C27B—C28B	5 (2)
O1—S1—C10—C15	−32.5 (5)	C26B—C27B—C28B—F2B	−171 (2)
N1—S1—C10—C15	79.6 (4)	C26B—C27B—C28B—C29B	−10 (4)
O2—S1—C10—C11	20.2 (5)	F2B—C28B—C29B—C30B	174 (3)
O1—S1—C10—C11	147.7 (5)	C27B—C28B—C29B—C30B	10 (5)
N1—S1—C10—C11	−100.2 (5)	C26B—C25—C30B—C29B	−1 (4)
C15—C10—C11—C12	0.5 (10)	C26A—C25—C30B—C29B	6 (3)
S1—C10—C11—C12	−179.7 (6)	C30A—C25—C30B—C29B	−153 (6)
C10—C11—C12—C13	0.6 (13)	S2—C25—C30B—C29B	175 (2)
C11—C12—C13—C14	−2.4 (16)	C28B—C29B—C30B—C25	−5 (5)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O1^ii	0.93	2.58	3.363 (5)	143
C6—H6···O3^iii	0.93	2.51	3.209 (4)	132

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