Synthesis and crystal structure of bis(1-{[(quinolin-8-yl)imino]methyl}pyrene-κ²N,N′)silver(I) tri­fluoro­methane­sulfonate

In the title salt, [Ag(qPyr)₂]CF₃SO₃ where qPyr = 1-(quinoline-2-yl­methyl­ene)amino­pyrene, the Ag^I atom exhibits a distorted tetra­hedral coordination by two chelating 1-(quinoline-2-yl­methyl­ene)amino­pyrene ligands.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.058
• wR factor = 0.181
• Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of         S1 Check
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00888 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      4.295 Check
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         83 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density           0 Note

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         65 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          2 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        273 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        273 Check
PLAT244_ALERT_4_G Low    'Solvent' Ueq as Compared to Neighbors of        C53 Check
PLAT728_ALERT_1_G D-H..A  Calc      169.00, Rep      139.90 Dev...      29.10 Degree
              C3   -H3   -O3        1.555   1.555   4.475 ....     #  186 Check
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        598 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         50 Note

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

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

---

Computing details

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and CrystalMaker (Palmer, 2014); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Bis(1-{[(quinolin-8-yl)imino]methyl}pyrene-κ²N,N')silver(I) trifluoromethanesulfonate

Crystal data

[Ag(C26H16N2)2]CF3SO3	F(000) = 1968
Mr = 969.75	Dx = 1.558 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.132 (1) Å	Cell parameters from 3637 reflections
b = 13.6108 (8) Å	θ = 2.5–18.3°
c = 18.9712 (11) Å	µ = 0.61 mm^−1
β = 110.887 (1)°	T = 273 K
V = 4133.0 (4) Å^3	Block, yellow
Z = 4	0.15 × 0.07 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer	4227 reflections with I > 2σ(I)
ω scans	Rint = 0.084
Absorption correction: multi-scan (SADABS; Bruker, 2012)	θmax = 25.3°, θmin = 2.5°
Tmin = 0.627, Tmax = 0.745	h = −20→20
35302 measured reflections	k = −16→16
7406 independent reflections	l = −22→22

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.058	w = 1/[σ^2(Fo^2) + (0.0931P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.181	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.60 e Å^−3
7406 reflections	Δρmin = −0.54 e Å^−3
587 parameters	Extinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
598 restraints	Extinction coefficient: 0.0017 (3)
Primary atom site location: structure-invariant direct methods

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
Ag1	0.16881 (3)	0.57600 (3)	0.42954 (2)	0.0629 (2)
N3	0.2384 (3)	0.6205 (3)	0.5499 (2)	0.0534 (11)
N1	0.0647 (3)	0.5949 (3)	0.3193 (2)	0.0501 (10)
N4	0.1663 (3)	0.4387 (3)	0.5090 (2)	0.0542 (11)
N2	0.2312 (3)	0.5968 (3)	0.3356 (2)	0.0507 (10)
C24	0.3877 (3)	0.5755 (4)	0.4763 (3)	0.0488 (12)
C25	0.4482 (3)	0.5944 (4)	0.5490 (3)	0.0558 (13)
C51	0.0012 (3)	0.3458 (3)	0.2843 (3)	0.0518 (12)
C4	0.0211 (4)	0.5902 (3)	0.1821 (3)	0.0583 (14)
C9	0.0843 (3)	0.5942 (3)	0.2556 (3)	0.0499 (12)
C50	0.0659 (3)	0.3530 (3)	0.3558 (3)	0.0501 (12)
C23	0.3550 (3)	0.4777 (4)	0.4605 (3)	0.0525 (13)
H23	0.3178	0.4627	0.4124	0.063*
C11	0.3654 (3)	0.6531 (4)	0.4234 (3)	0.0523 (12)
C3	−0.0622 (4)	0.5898 (4)	0.1778 (4)	0.0682 (16)
H3	−0.1050	0.5872	0.1309	0.082*
C35	0.2569 (3)	0.5489 (4)	0.6040 (3)	0.0514 (12)
C52	0.0219 (3)	0.3404 (3)	0.2178 (3)	0.0553 (13)
C2	−0.0806 (4)	0.5930 (4)	0.2405 (4)	0.0716 (17)
H2	−0.1359	0.5941	0.2376	0.086*
C49	0.1512 (3)	0.3484 (4)	0.3605 (3)	0.0545 (13)
H49	0.1938	0.3495	0.4076	0.065*
C27	0.2729 (3)	0.7083 (4)	0.5691 (3)	0.0618 (15)
H27	0.2599	0.7572	0.5324	0.074*
C47	0.1073 (4)	0.3406 (4)	0.2239 (3)	0.0594 (13)
C1	−0.0154 (4)	0.5946 (4)	0.3103 (4)	0.0623 (15)
H1	−0.0293	0.5956	0.3534	0.075*
C21	0.4332 (3)	0.4254 (4)	0.5877 (3)	0.0593 (14)
C8	0.1705 (3)	0.5955 (3)	0.2629 (3)	0.0512 (12)
C26	0.4708 (3)	0.5186 (4)	0.6047 (3)	0.0568 (13)
C22	0.3767 (3)	0.4072 (4)	0.5136 (3)	0.0593 (14)
H22	0.3540	0.3447	0.5013	0.071*
C38	−0.0409 (3)	0.3561 (4)	0.4127 (3)	0.0665 (16)
H38	−0.0553	0.3579	0.4555	0.080*
C37	0.0425 (3)	0.3630 (4)	0.4205 (3)	0.0551 (13)
C48	0.1704 (3)	0.3424 (4)	0.2978 (3)	0.0612 (14)
H48	0.2263	0.3393	0.3025	0.073*
C34	0.2188 (3)	0.4562 (4)	0.5850 (3)	0.0568 (13)
C14	0.4859 (3)	0.6873 (5)	0.5674 (3)	0.0659 (15)
C40	−0.0837 (3)	0.3446 (4)	0.2778 (3)	0.0592 (14)
C28	0.3280 (3)	0.7312 (5)	0.6420 (3)	0.0701 (16)
H28	0.3504	0.7940	0.6533	0.084*
C10	0.2978 (3)	0.6468 (4)	0.3491 (3)	0.0571 (14)
H10	0.3042	0.6817	0.3094	0.069*
C5	0.0460 (5)	0.5865 (4)	0.1188 (3)	0.0726 (17)
H5	0.0057	0.5855	0.0706	0.087*
C12	0.4057 (4)	0.7427 (4)	0.4422 (4)	0.0702 (16)
H12	0.3930	0.7923	0.4061	0.084*
C36	0.1001 (3)	0.3865 (4)	0.4959 (3)	0.0617 (14)
H36	0.0884	0.3624	0.5369	0.074*
C6	0.1272 (5)	0.5843 (4)	0.1275 (3)	0.0796 (18)
H6	0.1419	0.5796	0.0849	0.096*
C43	−0.0416 (4)	0.3368 (4)	0.1457 (3)	0.0679 (15)
C39	−0.1028 (4)	0.3465 (4)	0.3430 (4)	0.0701 (16)
H39	−0.1582	0.3413	0.3394	0.084*
C7	0.1901 (4)	0.5889 (4)	0.1982 (3)	0.0649 (15)
H7	0.2458	0.5877	0.2022	0.078*
C46	0.1265 (4)	0.3377 (4)	0.1576 (3)	0.0738 (16)
H46	0.1818	0.3394	0.1604	0.089*
C20	0.4531 (4)	0.3517 (5)	0.6449 (4)	0.0767 (17)
H20	0.4287	0.2898	0.6345	0.092*
C29	0.3478 (3)	0.6613 (5)	0.6949 (3)	0.0708 (16)
H29	0.3854	0.6753	0.7430	0.085*
C30	0.3127 (3)	0.5674 (5)	0.6789 (3)	0.0616 (14)
C41	−0.1471 (4)	0.3425 (4)	0.2036 (4)	0.0736 (16)
H41	−0.2031	0.3437	0.1986	0.088*
C42	−0.1271 (4)	0.3387 (4)	0.1413 (4)	0.0787 (17)
H42	−0.1696	0.3374	0.0942	0.094*
C13	0.4634 (4)	0.7603 (5)	0.5121 (4)	0.0780 (17)
H13	0.4882	0.8220	0.5231	0.094*
C31	0.3279 (4)	0.4912 (5)	0.7325 (3)	0.0789 (18)
H31	0.3634	0.5023	0.7819	0.095*
C17	0.5302 (3)	0.5385 (5)	0.6787 (3)	0.0716 (16)
C44	−0.0196 (5)	0.3334 (4)	0.0827 (4)	0.0834 (18)
H44	−0.0614	0.3318	0.0352	0.100*
C18	0.5467 (4)	0.4642 (6)	0.7317 (4)	0.0867 (19)
H18	0.5848	0.4760	0.7800	0.104*
C19	0.5093 (4)	0.3742 (6)	0.7158 (4)	0.092 (2)
H19	0.5219	0.3269	0.7537	0.110*
C45	0.0616 (5)	0.3323 (5)	0.0877 (4)	0.089 (2)
H45	0.0741	0.3279	0.0440	0.107*
C16	0.5670 (4)	0.6338 (6)	0.6939 (4)	0.0846 (18)
H16	0.6064	0.6475	0.7413	0.102*
C33	0.2366 (4)	0.3821 (5)	0.6390 (3)	0.0767 (18)
H33	0.2126	0.3202	0.6267	0.092*
C15	0.5460 (4)	0.7034 (6)	0.6414 (4)	0.0836 (19)
H15	0.5713	0.7647	0.6531	0.100*
C32	0.2919 (4)	0.4028 (6)	0.7128 (4)	0.091 (2)
H32	0.3037	0.3535	0.7491	0.109*
O3	0.8030 (4)	0.9279 (7)	0.4993 (4)	0.201 (4)
O2	0.6998 (7)	1.0435 (7)	0.4268 (5)	0.227 (4)
O1	0.6838 (6)	0.8797 (8)	0.3980 (5)	0.226 (4)
S1	0.72380 (15)	0.9402 (2)	0.45628 (13)	0.1150 (8)
C53	0.6710 (9)	0.9393 (10)	0.5169 (9)	0.159 (4)
F2	0.6754 (6)	0.8555 (6)	0.5521 (5)	0.248 (4)
F1	0.6960 (7)	0.9994 (8)	0.5715 (5)	0.265 (4)
F3	0.5898 (6)	0.9540 (8)	0.4846 (7)	0.282 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.0616 (3)	0.0814 (4)	0.0401 (3)	−0.0132 (2)	0.0113 (2)	0.0016 (2)
N3	0.050 (3)	0.065 (3)	0.043 (2)	−0.006 (2)	0.0139 (19)	−0.008 (2)
N1	0.051 (2)	0.042 (2)	0.054 (2)	0.0020 (18)	0.0144 (19)	−0.0029 (19)
N4	0.048 (2)	0.060 (3)	0.052 (2)	−0.0033 (19)	0.0148 (19)	0.000 (2)
N2	0.052 (2)	0.052 (3)	0.045 (2)	0.0022 (19)	0.0137 (19)	0.0049 (19)
C24	0.037 (3)	0.056 (3)	0.054 (3)	0.002 (2)	0.016 (2)	−0.002 (2)
C25	0.038 (3)	0.069 (3)	0.059 (3)	0.002 (2)	0.014 (2)	−0.007 (2)
C51	0.054 (3)	0.034 (3)	0.058 (3)	0.002 (2)	0.008 (2)	−0.005 (2)
C4	0.072 (3)	0.038 (3)	0.048 (3)	0.005 (2)	−0.001 (2)	−0.001 (2)
C9	0.055 (3)	0.044 (3)	0.040 (3)	0.003 (2)	0.004 (2)	0.004 (2)
C50	0.048 (3)	0.038 (3)	0.060 (3)	−0.003 (2)	0.015 (2)	−0.001 (2)
C23	0.043 (3)	0.054 (3)	0.057 (3)	0.004 (2)	0.014 (2)	−0.002 (2)
C11	0.043 (3)	0.055 (3)	0.061 (3)	0.001 (2)	0.021 (2)	0.001 (2)
C3	0.059 (3)	0.051 (3)	0.066 (4)	0.007 (3)	−0.012 (3)	0.002 (3)
C35	0.041 (3)	0.072 (3)	0.041 (3)	0.004 (2)	0.015 (2)	−0.006 (2)
C52	0.069 (3)	0.035 (3)	0.054 (3)	−0.006 (2)	0.013 (2)	−0.002 (2)
C2	0.058 (3)	0.053 (4)	0.085 (4)	0.002 (3)	0.003 (3)	−0.003 (3)
C49	0.046 (3)	0.056 (3)	0.057 (3)	−0.001 (2)	0.013 (2)	−0.008 (3)
C27	0.059 (3)	0.064 (3)	0.057 (3)	−0.006 (3)	0.014 (3)	−0.015 (3)
C47	0.073 (3)	0.039 (3)	0.064 (3)	−0.002 (2)	0.023 (3)	−0.005 (2)
C1	0.053 (3)	0.058 (4)	0.071 (4)	0.000 (2)	0.016 (3)	−0.007 (3)
C21	0.039 (3)	0.072 (3)	0.061 (3)	0.011 (2)	0.010 (2)	0.008 (2)
C8	0.061 (3)	0.046 (3)	0.040 (3)	0.007 (2)	0.010 (2)	0.010 (2)
C26	0.035 (3)	0.079 (3)	0.054 (3)	0.010 (2)	0.012 (2)	−0.002 (2)
C22	0.042 (3)	0.064 (3)	0.066 (3)	0.004 (2)	0.012 (2)	0.003 (3)
C38	0.055 (3)	0.069 (4)	0.078 (4)	−0.016 (3)	0.026 (3)	−0.011 (3)
C37	0.049 (3)	0.050 (3)	0.063 (3)	−0.008 (2)	0.016 (2)	−0.005 (2)
C48	0.057 (3)	0.053 (3)	0.073 (3)	0.000 (3)	0.023 (3)	−0.008 (3)
C34	0.050 (3)	0.073 (3)	0.043 (3)	0.002 (2)	0.011 (2)	0.002 (2)
C14	0.047 (3)	0.079 (4)	0.070 (3)	−0.010 (3)	0.019 (3)	−0.015 (3)
C40	0.049 (3)	0.039 (3)	0.077 (3)	−0.005 (2)	0.008 (2)	−0.005 (3)
C28	0.053 (3)	0.080 (4)	0.069 (4)	−0.007 (3)	0.011 (3)	−0.028 (3)
C10	0.060 (3)	0.054 (3)	0.058 (3)	0.003 (2)	0.022 (2)	0.009 (2)
C5	0.099 (4)	0.060 (4)	0.041 (3)	0.009 (3)	0.004 (3)	0.003 (3)
C12	0.060 (3)	0.064 (3)	0.083 (4)	−0.009 (3)	0.022 (3)	0.000 (3)
C36	0.060 (3)	0.065 (3)	0.059 (3)	−0.009 (3)	0.020 (3)	0.001 (3)
C6	0.107 (4)	0.080 (4)	0.044 (3)	0.016 (4)	0.018 (3)	0.008 (3)
C43	0.085 (4)	0.046 (3)	0.057 (3)	0.001 (3)	0.006 (3)	−0.005 (3)
C39	0.052 (3)	0.062 (4)	0.092 (4)	−0.006 (3)	0.020 (3)	−0.013 (3)
C7	0.081 (4)	0.066 (4)	0.048 (3)	0.010 (3)	0.022 (3)	0.010 (3)
C46	0.101 (4)	0.056 (4)	0.069 (4)	0.008 (3)	0.037 (3)	−0.003 (3)
C20	0.057 (4)	0.091 (4)	0.080 (4)	0.021 (3)	0.020 (3)	0.025 (3)
C29	0.051 (3)	0.097 (4)	0.055 (3)	0.002 (3)	0.007 (3)	−0.021 (3)
C30	0.045 (3)	0.091 (4)	0.043 (3)	0.007 (3)	0.009 (2)	−0.008 (2)
C41	0.053 (3)	0.057 (4)	0.089 (4)	−0.004 (3)	−0.001 (3)	−0.008 (3)
C42	0.080 (4)	0.055 (4)	0.076 (4)	0.000 (3)	−0.003 (3)	−0.007 (3)
C13	0.061 (4)	0.074 (4)	0.094 (4)	−0.019 (3)	0.021 (3)	−0.017 (3)
C31	0.064 (4)	0.111 (4)	0.048 (3)	0.007 (3)	0.002 (3)	0.005 (3)
C17	0.044 (3)	0.107 (4)	0.058 (3)	0.011 (3)	0.011 (3)	−0.011 (3)
C44	0.112 (5)	0.061 (4)	0.065 (4)	0.008 (4)	0.016 (3)	−0.002 (3)
C18	0.057 (4)	0.131 (5)	0.062 (4)	0.018 (3)	0.009 (3)	0.007 (4)
C19	0.067 (4)	0.124 (5)	0.071 (4)	0.027 (4)	0.008 (3)	0.024 (4)
C45	0.129 (5)	0.069 (4)	0.066 (4)	0.012 (4)	0.030 (4)	−0.005 (3)
C16	0.054 (4)	0.122 (5)	0.069 (4)	−0.002 (3)	0.012 (3)	−0.023 (3)
C33	0.066 (4)	0.088 (4)	0.065 (3)	−0.005 (3)	0.009 (3)	0.015 (3)
C15	0.056 (4)	0.105 (5)	0.081 (4)	−0.018 (3)	0.014 (3)	−0.030 (3)
C32	0.086 (5)	0.113 (5)	0.053 (4)	0.005 (4)	0.000 (3)	0.023 (3)
O3	0.100 (4)	0.401 (13)	0.090 (4)	0.045 (5)	0.021 (4)	0.048 (5)
O2	0.256 (10)	0.187 (6)	0.246 (10)	0.016 (6)	0.099 (8)	0.088 (6)
O1	0.201 (8)	0.253 (8)	0.170 (7)	−0.016 (6)	0.000 (6)	−0.078 (7)
S1	0.0939 (16)	0.157 (2)	0.0820 (15)	−0.0174 (15)	0.0165 (12)	−0.0017 (14)
C53	0.173 (8)	0.130 (7)	0.210 (9)	−0.030 (6)	0.112 (7)	−0.010 (6)
F2	0.316 (10)	0.199 (7)	0.310 (9)	−0.005 (6)	0.210 (8)	0.070 (6)
F1	0.336 (10)	0.268 (9)	0.281 (9)	−0.081 (7)	0.221 (8)	−0.093 (7)
F3	0.160 (6)	0.309 (10)	0.416 (12)	0.006 (6)	0.151 (7)	0.077 (8)

Geometric parameters (Å, º)

Ag1—N3	2.249 (4)	C48—H48	0.9300
Ag1—N1	2.228 (4)	C34—C33	1.392 (8)
Ag1—N4	2.411 (4)	C14—C13	1.396 (8)
Ag1—N2	2.399 (4)	C14—C15	1.431 (8)
N3—C35	1.368 (7)	C40—C39	1.387 (8)
N3—C27	1.326 (6)	C40—C41	1.440 (7)
N1—C9	1.364 (7)	C28—H28	0.9300
N1—C1	1.321 (7)	C28—C29	1.336 (8)
N4—C34	1.420 (7)	C10—H10	0.9300
N4—C36	1.286 (6)	C5—H5	0.9300
N2—C8	1.400 (6)	C5—C6	1.342 (9)
N2—C10	1.274 (6)	C12—H12	0.9300
C24—C25	1.424 (7)	C12—C13	1.364 (8)
C24—C23	1.434 (7)	C36—H36	0.9300
C24—C11	1.413 (7)	C6—H6	0.9300
C25—C26	1.427 (7)	C6—C7	1.391 (8)
C25—C14	1.406 (7)	C43—C42	1.437 (9)
C51—C50	1.416 (7)	C43—C44	1.377 (9)
C51—C52	1.428 (8)	C39—H39	0.9300
C51—C40	1.417 (7)	C7—H7	0.9300
C4—C9	1.430 (7)	C46—H46	0.9300
C4—C3	1.400 (8)	C46—C45	1.395 (8)
C4—C5	1.412 (9)	C20—H20	0.9300
C9—C8	1.434 (7)	C20—C19	1.382 (9)
C50—C49	1.434 (7)	C29—H29	0.9300
C50—C37	1.426 (7)	C29—C30	1.400 (8)
C23—H23	0.9300	C30—C31	1.410 (8)
C23—C22	1.344 (7)	C41—H41	0.9300
C11—C10	1.473 (7)	C41—C42	1.344 (9)
C11—C12	1.384 (7)	C42—H42	0.9300
C3—H3	0.9300	C13—H13	0.9300
C3—C2	1.336 (9)	C31—H31	0.9300
C35—C34	1.407 (7)	C31—C32	1.343 (9)
C35—C30	1.424 (7)	C17—C18	1.382 (9)
C52—C47	1.426 (8)	C17—C16	1.427 (9)
C52—C43	1.413 (7)	C44—H44	0.9300
C2—H2	0.9300	C44—C45	1.359 (9)
C2—C1	1.396 (8)	C18—H18	0.9300
C49—H49	0.9300	C18—C19	1.366 (10)
C49—C48	1.346 (7)	C19—H19	0.9300
C27—H27	0.9300	C45—H45	0.9300
C27—C28	1.404 (7)	C16—H16	0.9300
C47—C48	1.433 (7)	C16—C15	1.327 (9)
C47—C46	1.410 (8)	C33—H33	0.9300
C1—H1	0.9300	C33—C32	1.411 (8)
C21—C26	1.406 (8)	C15—H15	0.9300
C21—C22	1.417 (8)	C32—H32	0.9300
C21—C20	1.426 (8)	O3—S1	1.321 (7)
C8—C7	1.386 (7)	O2—S1	1.515 (9)
C26—C17	1.436 (7)	O1—S1	1.352 (8)
C22—H22	0.9300	S1—C53	1.698 (11)
C38—H38	0.9300	C53—F2	1.309 (13)
C38—C37	1.387 (7)	C53—F1	1.268 (13)
C38—C39	1.375 (7)	C53—F3	1.320 (15)
C37—C36	1.454 (7)
N3—Ag1—N4	72.24 (15)	C51—C40—C41	118.5 (6)
N3—Ag1—N2	120.45 (15)	C39—C40—C51	119.0 (5)
N1—Ag1—N3	151.52 (16)	C39—C40—C41	122.5 (6)
N1—Ag1—N4	119.33 (15)	C27—C28—H28	120.5
N1—Ag1—N2	73.09 (15)	C29—C28—C27	118.9 (6)
N2—Ag1—N4	131.88 (14)	C29—C28—H28	120.5
C35—N3—Ag1	117.9 (3)	N2—C10—C11	124.4 (5)
C27—N3—Ag1	123.0 (4)	N2—C10—H10	117.8
C27—N3—C35	118.3 (5)	C11—C10—H10	117.8
C9—N1—Ag1	117.5 (3)	C4—C5—H5	119.6
C1—N1—Ag1	124.6 (4)	C6—C5—C4	120.8 (6)
C1—N1—C9	117.3 (5)	C6—C5—H5	119.6
C34—N4—Ag1	111.0 (3)	C11—C12—H12	119.1
C36—N4—Ag1	121.2 (4)	C13—C12—C11	121.8 (6)
C36—N4—C34	119.0 (5)	C13—C12—H12	119.1
C8—N2—Ag1	111.0 (3)	N4—C36—C37	123.7 (5)
C10—N2—Ag1	121.2 (4)	N4—C36—H36	118.2
C10—N2—C8	120.1 (5)	C37—C36—H36	118.2
C25—C24—C23	117.8 (5)	C5—C6—H6	119.0
C11—C24—C25	118.2 (5)	C5—C6—C7	121.9 (6)
C11—C24—C23	124.0 (5)	C7—C6—H6	119.0
C24—C25—C26	119.8 (5)	C52—C43—C42	118.2 (6)
C14—C25—C24	121.0 (5)	C44—C43—C52	119.2 (6)
C14—C25—C26	119.2 (5)	C44—C43—C42	122.6 (6)
C50—C51—C52	119.6 (5)	C38—C39—C40	120.9 (6)
C50—C51—C40	120.8 (5)	C38—C39—H39	119.6
C40—C51—C52	119.6 (5)	C40—C39—H39	119.6
C3—C4—C9	117.4 (6)	C8—C7—C6	120.6 (6)
C3—C4—C5	124.1 (6)	C8—C7—H7	119.7
C5—C4—C9	118.5 (6)	C6—C7—H7	119.7
N1—C9—C4	121.6 (5)	C47—C46—H46	120.4
N1—C9—C8	119.0 (4)	C45—C46—C47	119.3 (7)
C4—C9—C8	119.4 (5)	C45—C46—H46	120.4
C51—C50—C49	119.2 (5)	C21—C20—H20	120.7
C51—C50—C37	117.9 (5)	C19—C20—C21	118.6 (7)
C37—C50—C49	122.9 (5)	C19—C20—H20	120.7
C24—C23—H23	119.2	C28—C29—H29	119.5
C22—C23—C24	121.5 (5)	C28—C29—C30	120.9 (5)
C22—C23—H23	119.2	C30—C29—H29	119.5
C24—C11—C10	123.9 (5)	C29—C30—C35	117.5 (5)
C12—C11—C24	119.5 (5)	C29—C30—C31	124.1 (6)
C12—C11—C10	116.5 (5)	C31—C30—C35	118.4 (6)
C4—C3—H3	119.8	C40—C41—H41	119.3
C2—C3—C4	120.4 (6)	C42—C41—C40	121.4 (6)
C2—C3—H3	119.8	C42—C41—H41	119.3
N3—C35—C34	118.9 (5)	C43—C42—H42	119.2
N3—C35—C30	121.1 (5)	C41—C42—C43	121.6 (6)
C34—C35—C30	120.0 (5)	C41—C42—H42	119.2
C47—C52—C51	119.9 (5)	C14—C13—H13	119.5
C43—C52—C51	120.6 (6)	C12—C13—C14	121.1 (6)
C43—C52—C47	119.5 (5)	C12—C13—H13	119.5
C3—C2—H2	120.5	C30—C31—H31	119.7
C3—C2—C1	118.9 (6)	C32—C31—C30	120.6 (6)
C1—C2—H2	120.5	C32—C31—H31	119.7
C50—C49—H49	119.6	C18—C17—C26	117.6 (6)
C48—C49—C50	120.9 (5)	C18—C17—C16	123.9 (6)
C48—C49—H49	119.6	C16—C17—C26	118.5 (6)
N3—C27—H27	118.4	C43—C44—H44	119.0
N3—C27—C28	123.2 (6)	C45—C44—C43	121.9 (7)
C28—C27—H27	118.4	C45—C44—H44	119.0
C52—C47—C48	118.3 (5)	C17—C18—H18	118.8
C46—C47—C52	119.1 (5)	C19—C18—C17	122.5 (7)
C46—C47—C48	122.6 (6)	C19—C18—H18	118.8
N1—C1—C2	124.4 (6)	C20—C19—H19	119.2
N1—C1—H1	117.8	C18—C19—C20	121.5 (7)
C2—C1—H1	117.8	C18—C19—H19	119.2
C26—C21—C22	118.7 (5)	C46—C45—H45	119.5
C26—C21—C20	119.7 (5)	C44—C45—C46	121.0 (7)
C22—C21—C20	121.6 (6)	C44—C45—H45	119.5
N2—C8—C9	118.2 (5)	C17—C16—H16	119.5
C7—C8—N2	123.0 (5)	C15—C16—C17	121.0 (6)
C7—C8—C9	118.7 (5)	C15—C16—H16	119.5
C25—C26—C17	119.8 (6)	C34—C33—H33	120.7
C21—C26—C25	120.1 (5)	C34—C33—C32	118.7 (6)
C21—C26—C17	120.0 (6)	C32—C33—H33	120.7
C23—C22—C21	121.8 (5)	C14—C15—H15	118.8
C23—C22—H22	119.1	C16—C15—C14	122.3 (7)
C21—C22—H22	119.1	C16—C15—H15	118.8
C37—C38—H38	119.3	C31—C32—C33	122.2 (6)
C39—C38—H38	119.3	C31—C32—H32	118.9
C39—C38—C37	121.4 (6)	C33—C32—H32	118.9
C50—C37—C36	124.6 (5)	O3—S1—O2	115.4 (6)
C38—C37—C50	119.7 (5)	O3—S1—O1	122.5 (6)
C38—C37—C36	115.6 (5)	O3—S1—C53	105.0 (6)
C49—C48—C47	121.9 (5)	O2—S1—C53	96.7 (6)
C49—C48—H48	119.0	O1—S1—O2	105.8 (6)
C47—C48—H48	119.0	O1—S1—C53	108.2 (7)
C35—C34—N4	118.6 (5)	F2—C53—S1	113.8 (10)
C33—C34—N4	121.2 (5)	F2—C53—F3	103.2 (10)
C33—C34—C35	120.0 (5)	F1—C53—S1	116.2 (9)
C25—C14—C15	119.1 (6)	F1—C53—F2	101.8 (13)
C13—C14—C25	118.3 (5)	F1—C53—F3	105.9 (12)
C13—C14—C15	122.6 (6)	F3—C53—S1	114.4 (12)
Ag1—N3—C35—C34	−11.9 (6)	C49—C50—C37—C36	11.2 (8)
Ag1—N3—C35—C30	169.1 (4)	C27—N3—C35—C34	178.1 (5)
Ag1—N3—C27—C28	−168.9 (4)	C27—N3—C35—C30	−0.9 (7)
Ag1—N1—C9—C4	170.0 (3)	C27—C28—C29—C30	−1.7 (9)
Ag1—N1—C9—C8	−8.7 (6)	C47—C52—C43—C42	−178.7 (5)
Ag1—N1—C1—C2	−170.8 (4)	C47—C52—C43—C44	0.1 (8)
Ag1—N4—C34—C35	5.4 (6)	C47—C46—C45—C44	2.4 (9)
Ag1—N4—C34—C33	−170.8 (4)	C1—N1—C9—C4	−1.9 (7)
Ag1—N4—C36—C37	36.1 (7)	C1—N1—C9—C8	179.4 (4)
Ag1—N2—C8—C9	7.1 (5)	C21—C26—C17—C18	−1.5 (8)
Ag1—N2—C8—C7	−168.5 (4)	C21—C26—C17—C16	180.0 (5)
Ag1—N2—C10—C11	33.2 (7)	C21—C20—C19—C18	−1.1 (10)
N3—C35—C34—N4	3.7 (7)	C8—N2—C10—C11	−179.9 (5)
N3—C35—C34—C33	179.9 (5)	C26—C25—C14—C13	179.6 (5)
N3—C35—C30—C29	0.0 (8)	C26—C25—C14—C15	0.2 (8)
N3—C35—C30—C31	178.8 (5)	C26—C21—C22—C23	−3.5 (8)
N3—C27—C28—C29	0.7 (9)	C26—C21—C20—C19	−0.1 (9)
N1—C9—C8—N2	0.4 (7)	C26—C17—C18—C19	0.3 (10)
N1—C9—C8—C7	176.3 (4)	C26—C17—C16—C15	1.2 (9)
N4—C34—C33—C32	177.4 (6)	C22—C21—C26—C25	3.6 (8)
N2—C8—C7—C6	177.6 (5)	C22—C21—C26—C17	−178.2 (5)
C24—C25—C26—C21	−0.2 (8)	C22—C21—C20—C19	179.4 (6)
C24—C25—C26—C17	−178.4 (5)	C38—C37—C36—N4	−146.2 (6)
C24—C25—C14—C13	−0.9 (8)	C37—C50—C49—C48	−177.7 (5)
C24—C25—C14—C15	179.7 (5)	C37—C38—C39—C40	−0.8 (9)
C24—C23—C22—C21	−0.2 (8)	C48—C47—C46—C45	177.5 (5)
C24—C11—C10—N2	32.7 (8)	C34—N4—C36—C37	−179.3 (5)
C24—C11—C12—C13	−3.6 (9)	C34—C35—C30—C29	−179.1 (5)
C25—C24—C23—C22	3.6 (7)	C34—C35—C30—C31	−0.2 (8)
C25—C24—C11—C10	−173.5 (5)	C34—C33—C32—C31	−0.3 (11)
C25—C24—C11—C12	3.3 (7)	C14—C25—C26—C21	179.3 (5)
C25—C26—C17—C18	176.7 (5)	C14—C25—C26—C17	1.1 (8)
C25—C26—C17—C16	−1.8 (8)	C40—C51—C50—C49	176.5 (4)
C25—C14—C13—C12	0.8 (9)	C40—C51—C50—C37	−2.4 (7)
C25—C14—C15—C16	−0.8 (9)	C40—C51—C52—C47	−179.4 (4)
C51—C50—C49—C48	3.5 (7)	C40—C51—C52—C43	1.8 (7)
C51—C50—C37—C38	6.0 (7)	C40—C41—C42—C43	0.0 (9)
C51—C50—C37—C36	−169.9 (5)	C28—C29—C30—C35	1.4 (8)
C51—C52—C47—C48	2.4 (7)	C28—C29—C30—C31	−177.4 (6)
C51—C52—C47—C46	−178.5 (5)	C10—N2—C8—C9	−142.8 (5)
C51—C52—C43—C42	0.1 (8)	C10—N2—C8—C7	41.5 (7)
C51—C52—C43—C44	178.9 (5)	C10—C11—C12—C13	173.4 (6)
C51—C40—C39—C38	4.4 (8)	C5—C4—C9—N1	−178.0 (5)
C51—C40—C41—C42	1.9 (8)	C5—C4—C9—C8	0.7 (7)
C4—C9—C8—N2	−178.3 (4)	C5—C4—C3—C2	179.7 (5)
C4—C9—C8—C7	−2.5 (7)	C5—C6—C7—C8	0.4 (9)
C4—C3—C2—C1	−1.4 (8)	C12—C11—C10—N2	−144.2 (6)
C4—C5—C6—C7	−2.2 (9)	C36—N4—C34—C35	−142.6 (6)
C9—N1—C1—C2	0.5 (7)	C36—N4—C34—C33	41.3 (8)
C9—C4—C3—C2	0.0 (7)	C43—C52—C47—C48	−178.8 (5)
C9—C4—C5—C6	1.6 (8)	C43—C52—C47—C46	0.3 (7)
C9—C8—C7—C6	2.0 (8)	C43—C44—C45—C46	−2.0 (10)
C50—C51—C52—C47	1.1 (7)	C39—C38—C37—C50	−4.5 (8)
C50—C51—C52—C43	−177.7 (4)	C39—C38—C37—C36	171.7 (5)
C50—C51—C40—C39	−2.7 (7)	C39—C40—C41—C42	−178.7 (6)
C50—C51—C40—C41	176.7 (5)	C46—C47—C48—C49	177.8 (5)
C50—C49—C48—C47	0.2 (8)	C20—C21—C26—C25	−176.9 (5)
C50—C37—C36—N4	29.9 (9)	C20—C21—C26—C17	1.3 (8)
C23—C24—C25—C26	−3.4 (7)	C20—C21—C22—C23	177.0 (5)
C23—C24—C25—C14	177.1 (5)	C29—C30—C31—C32	180.0 (6)
C23—C24—C11—C10	8.4 (8)	C30—C35—C34—N4	−177.2 (5)
C23—C24—C11—C12	−174.8 (5)	C30—C35—C34—C33	−1.0 (8)
C11—C24—C25—C26	178.4 (5)	C30—C31—C32—C33	−1.0 (11)
C11—C24—C25—C14	−1.1 (8)	C41—C40—C39—C38	−175.0 (5)
C11—C24—C23—C22	−178.3 (5)	C42—C43—C44—C45	179.5 (6)
C11—C12—C13—C14	1.5 (10)	C13—C14—C15—C16	179.8 (6)
C3—C4—C9—N1	1.7 (7)	C17—C18—C19—C20	0.9 (11)
C3—C4—C9—C8	−179.6 (4)	C17—C16—C15—C14	0.1 (10)
C3—C4—C5—C6	−178.1 (5)	C44—C43—C42—C41	−179.7 (6)
C3—C2—C1—N1	1.2 (8)	C18—C17—C16—C15	−177.3 (6)
C35—N3—C27—C28	0.6 (8)	C16—C17—C18—C19	178.8 (6)
C35—C34—C33—C32	1.3 (9)	C15—C14—C13—C12	−179.9 (6)
C35—C30—C31—C32	1.2 (9)	O3—S1—C53—F2	−63.8 (13)
C52—C51—C50—C49	−4.0 (7)	O3—S1—C53—F1	53.9 (14)
C52—C51—C50—C37	177.1 (4)	O3—S1—C53—F3	177.8 (10)
C52—C51—C40—C39	177.8 (5)	O2—S1—C53—F2	177.6 (12)
C52—C51—C40—C41	−2.7 (7)	O2—S1—C53—F1	−64.7 (14)
C52—C47—C48—C49	−3.1 (8)	O2—S1—C53—F3	59.3 (11)
C52—C47—C46—C45	−1.5 (8)	O1—S1—C53—F2	68.5 (14)
C52—C43—C42—C41	−1.0 (8)	O1—S1—C53—F1	−173.7 (12)
C52—C43—C44—C45	0.8 (9)	O1—S1—C53—F3	−49.8 (12)
C49—C50—C37—C38	−172.9 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3^i	0.93	2.44	3.359 (10)	140

Symmetry code: (i) x−1, −y+3/2, z−1/2.