Bis{5-methyl-4-[(Z)-(1-naphthyl­amino)­phenyl­methyl­ene]-2-phenyl-3H-pyrazol-3-one-κ²N,N′}silver(I) hexa­fluoro­phosphate

In the title complex, [Ag(C₂₇H₂₁N₃O)₂]PF₆, the Ag atom occupies a centre of symmetry, resulting in linear N—Ag—N coordination [Ag—N = 2.124 (2) Å]. The P atom of the counter-anion has site symmetry.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.037
• wR factor = 0.097
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.693     0.837
            Tmin' and Tmax expected:      0.789     0.851
            RR' =      0.893
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.89
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.02
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.57 Ratio
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C15
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....         P1
PLAT414_ALERT_2_C Short Intra D-H..H-X       H3N    ..  H26     ..       1.97 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 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
   3 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

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97; molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Bis{5-methyl-4-[(Z)-(1-naphthylamino)phenylmethylene]-2-phenyl-3H-pyrazol- 3-one-κ²N,N'}silver(I) hexafluorophosphate

Crystal data

[Ag(C27H21N3O)2]PF6	Z = 1
Mr = 1059.78	F(000) = 540
Triclinic, P1	Dx = 1.500 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.655 (1) Å	Cell parameters from 974 reflections
b = 10.859 (1) Å	θ = 2.6–26.8°
c = 11.384 (1) Å	µ = 0.54 mm^−1
α = 88.695 (2)°	T = 298 K
β = 79.453 (2)°	Block, yellow
γ = 88.840 (2)°	0.43 × 0.36 × 0.30 mm
V = 1172.9 (2) Å^3

Data collection

Bruker SMART area-detector diffractometer	5042 independent reflections
Radiation source: fine-focus sealed tube	3499 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.693, Tmax = 0.837	k = −13→13
10053 measured reflections	l = −14→14

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	H-atom parameters constrained
S = 0.91	w = 1/[σ^2(Fo^2) + (0.0582P)^2] where P = (Fo^2 + 2Fc^2)/3
5042 reflections	(Δ/σ)max = 0.001
320 parameters	Δρmax = 0.55 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

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

	x	y	z	Uiso*/Ueq
Ag1	0.5000	0.5000	0.5000	0.0607 (1)
P1	0.0000	0.0000	0.5000	0.0483 (2)
F1	0.0368 (3)	0.1211 (2)	0.4284 (3)	0.151 (1)
F2	0.1292 (2)	−0.0669 (3)	0.4274 (2)	0.143 (1)
F3	0.0935 (2)	0.0342 (2)	0.5935 (2)	0.107 (1)
O1	0.3165 (2)	0.3379 (2)	0.1110 (2)	0.058 (1)
N1	0.4156 (2)	0.5020 (2)	0.3403 (2)	0.046 (1)
N2	0.4006 (2)	0.3933 (2)	0.2798 (2)	0.045 (1)
N3	0.2094 (2)	0.5354 (2)	0.0134 (2)	0.052 (1)
C1	0.4626 (2)	0.2799 (2)	0.3110 (2)	0.040 (1)
C2	0.3867 (3)	0.1745 (2)	0.3171 (2)	0.052 (1)
C3	0.4489 (3)	0.0648 (2)	0.3435 (3)	0.066 (1)
C4	0.5849 (3)	0.0609 (3)	0.3635 (2)	0.064 (1)
C5	0.6591 (3)	0.1656 (3)	0.3583 (2)	0.059 (1)
C6	0.6000 (3)	0.2768 (2)	0.3298 (2)	0.048 (1)
C7	0.3372 (3)	0.4163 (2)	0.1837 (2)	0.045 (1)
C8	0.3093 (2)	0.5472 (2)	0.1837 (2)	0.043 (1)
C9	0.3611 (3)	0.5923 (2)	0.2837 (2)	0.045 (1)
C10	0.3570 (4)	0.7197 (2)	0.3299 (3)	0.069 (1)
C11	0.2498 (2)	0.6069 (2)	0.0938 (2)	0.042 (1)
C12	0.2410 (3)	0.7428 (2)	0.0823 (2)	0.042 (1)
C13	0.3410 (3)	0.8026 (3)	0.0002 (2)	0.061 (1)
C14	0.3319 (4)	0.9293 (3)	−0.0140 (3)	0.088 (1)
C15	0.2251 (5)	0.9943 (3)	0.0528 (3)	0.101 (1)
C16	0.1256 (4)	0.9354 (3)	0.1348 (3)	0.084 (1)
C17	0.1337 (3)	0.8097 (2)	0.1506 (2)	0.058 (1)
C18	0.1503 (3)	0.5627 (2)	−0.0901 (2)	0.049 (1)
C19	0.0724 (3)	0.6661 (3)	−0.1031 (2)	0.059 (1)
C20	0.0192 (3)	0.6886 (3)	−0.2085 (3)	0.069 (1)
C21	0.0433 (3)	0.6070 (3)	−0.2977 (3)	0.073 (1)
C22	0.1183 (3)	0.4979 (3)	−0.2865 (2)	0.061 (1)
C23	0.1453 (4)	0.4087 (4)	−0.3791 (3)	0.083 (1)
C24	0.2149 (4)	0.3042 (4)	−0.3675 (3)	0.089 (1)
C25	0.2658 (4)	0.2778 (3)	−0.2624 (3)	0.082 (1)
C26	0.2481 (3)	0.3605 (3)	−0.1723 (3)	0.064 (1)
C27	0.1744 (3)	0.4722 (2)	−0.1809 (2)	0.050 (1)
H3n	0.2213	0.4579	0.0264	0.063*
H2	0.2946	0.1768	0.3036	0.062*
H3	0.3982	−0.0076	0.3480	0.080*
H4	0.6261	−0.0140	0.3807	0.077*
H5	0.7503	0.1629	0.3740	0.070*
H6	0.6520	0.3486	0.3234	0.058*
H10a	0.4133	0.7229	0.3910	0.103*
H10b	0.2614	0.7427	0.3627	0.103*
H10c	0.3935	0.7757	0.2658	0.103*
H13	0.4142	0.7582	−0.0454	0.073*
H14	0.3992	0.9700	−0.0694	0.106*
H15	0.2196	1.0794	0.0427	0.122*
H16	0.0525	0.9804	0.1799	0.100*
H17	0.0670	0.7699	0.2072	0.070*
H19	0.0542	0.7224	−0.0417	0.070*
H20	−0.0330	0.7601	−0.2168	0.083*
H21	0.0093	0.6238	−0.3678	0.088*
H23	0.1127	0.4248	−0.4500	0.100*
H24	0.2299	0.2483	−0.4294	0.107*
H25	0.3122	0.2032	−0.2537	0.098*
H26	0.2855	0.3427	−0.1041	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.0914 (3)	0.0491 (2)	0.0542 (2)	0.0093 (2)	−0.0474 (2)	−0.0071 (1)
P1	0.0453 (5)	0.0486 (5)	0.0531 (5)	0.0120 (4)	−0.0158 (4)	−0.0010 (4)
F1	0.152 (2)	0.113 (2)	0.204 (3)	−0.037 (2)	−0.080 (2)	0.091 (2)
F2	0.103 (2)	0.216 (3)	0.109 (2)	0.089 (2)	−0.024 (1)	−0.058 (2)
F3	0.108 (2)	0.112 (2)	0.122 (2)	0.021 (1)	−0.076 (1)	−0.028 (1)
O1	0.085 (1)	0.041 (1)	0.060 (1)	0.015 (1)	−0.043 (1)	−0.015 (1)
N1	0.064 (1)	0.036 (1)	0.045 (1)	0.007 (1)	−0.029 (1)	−0.008 (1)
N2	0.063 (1)	0.033 (1)	0.048 (1)	0.006 (1)	−0.031 (1)	−0.005 (1)
N3	0.077 (2)	0.039 (1)	0.050 (1)	0.010 (1)	−0.037 (1)	−0.005 (1)
C1	0.050 (1)	0.037 (1)	0.034 (1)	0.005 (1)	−0.014 (1)	−0.001 (1)
C2	0.053 (2)	0.045 (1)	0.060 (2)	−0.002 (1)	−0.018 (1)	−0.002 (1)
C3	0.091 (2)	0.036 (1)	0.073 (2)	−0.007 (1)	−0.018 (2)	0.005 (1)
C4	0.086 (2)	0.046 (2)	0.061 (2)	0.023 (2)	−0.019 (2)	0.005 (1)
C5	0.058 (2)	0.061 (2)	0.060 (2)	0.016 (1)	−0.022 (1)	0.003 (1)
C6	0.051 (2)	0.047 (1)	0.050 (1)	−0.001 (1)	−0.019 (1)	0.004 (1)
C7	0.054 (2)	0.040 (1)	0.046 (1)	0.009 (1)	−0.025 (1)	−0.005 (1)
C8	0.056 (2)	0.035 (1)	0.043 (1)	0.008 (1)	−0.024 (1)	−0.006 (1)
C9	0.059 (2)	0.038 (1)	0.042 (1)	0.007 (1)	−0.023 (1)	−0.005 (1)
C10	0.112 (2)	0.041 (1)	0.066 (2)	0.016 (2)	−0.052 (2)	−0.016 (1)
C11	0.049 (1)	0.043 (1)	0.037 (1)	0.009 (1)	−0.016 (1)	−0.006 (1)
C12	0.053 (1)	0.040 (1)	0.036 (1)	0.007 (1)	−0.019 (1)	−0.002 (1)
C13	0.067 (2)	0.064 (2)	0.051 (2)	0.000 (2)	−0.008 (1)	−0.006 (1)
C14	0.125 (3)	0.065 (2)	0.072 (2)	−0.026 (2)	−0.009 (2)	0.014 (2)
C15	0.186 (4)	0.043 (2)	0.078 (2)	0.013 (2)	−0.031 (3)	0.002 (2)
C16	0.129 (3)	0.057 (2)	0.061 (2)	0.039 (2)	−0.012 (2)	−0.008 (2)
C17	0.073 (2)	0.055 (2)	0.045 (1)	0.017 (1)	−0.006 (1)	0.000 (1)
C18	0.058 (2)	0.050 (1)	0.044 (1)	−0.002 (1)	−0.025 (1)	0.000 (1)
C19	0.067 (2)	0.057 (2)	0.059 (2)	0.006 (1)	−0.034 (1)	−0.001 (1)
C20	0.077 (2)	0.068 (2)	0.072 (2)	0.001 (2)	−0.045 (2)	0.011 (2)
C21	0.085 (2)	0.089 (2)	0.057 (2)	−0.017 (2)	−0.043 (2)	0.018 (2)
C22	0.070 (2)	0.075 (2)	0.045 (1)	−0.025 (2)	−0.024 (1)	0.002 (1)
C23	0.106 (3)	0.101 (3)	0.050 (2)	−0.028 (2)	−0.029 (2)	−0.010 (2)
C24	0.115 (3)	0.094 (3)	0.062 (2)	−0.019 (2)	−0.019 (2)	−0.030 (2)
C25	0.102 (3)	0.070 (2)	0.076 (2)	0.002 (2)	−0.021 (2)	−0.026 (2)
C26	0.079 (2)	0.061 (2)	0.057 (2)	0.002 (2)	−0.026 (2)	−0.013 (1)
C27	0.057 (2)	0.055 (2)	0.044 (1)	−0.012 (1)	−0.017 (1)	−0.002 (1)

Geometric parameters (Å, º)

Ag1—N1	2.124 (2)	C18—C19	1.359 (4)
Ag1—N1^i	2.124 (2)	C18—C27	1.427 (3)
P1—F1	1.544 (2)	C19—C20	1.403 (3)
P1—F1^ii	1.544 (2)	C20—C21	1.348 (4)
P1—F2	1.543 (2)	C21—C22	1.391 (4)
P1—F2^ii	1.543 (2)	C22—C27	1.426 (3)
P1—F3	1.571 (2)	C22—C23	1.433 (4)
P1—F3^ii	1.571 (2)	C23—C24	1.323 (5)
O1—C7	1.244 (3)	C24—C25	1.396 (5)
N1—C9	1.314 (3)	C25—C26	1.363 (4)
N1—N2	1.403 (2)	C26—C27	1.404 (4)
N2—C7	1.365 (3)	N3—H3n	0.86
N2—C1	1.423 (3)	C2—H2	0.93
N3—C11	1.330 (3)	C3—H3	0.93
N3—C18	1.423 (3)	C4—H4	0.93
C1—C2	1.365 (3)	C5—H5	0.93
C1—C6	1.382 (3)	C6—H6	0.93
C2—C3	1.375 (4)	C10—H10a	0.96
C3—C4	1.373 (4)	C10—H10b	0.96
C4—C5	1.351 (4)	C10—H10c	0.96
C5—C6	1.383 (3)	C13—H13	0.93
C7—C8	1.442 (3)	C14—H14	0.93
C8—C11	1.402 (3)	C15—H15	0.93
C8—C9	1.425 (3)	C16—H16	0.93
C9—C10	1.489 (3)	C17—H17	0.93
C11—C12	1.481 (3)	C19—H19	0.93
C12—C13	1.376 (4)	C20—H20	0.93
C12—C17	1.381 (3)	C21—H21	0.93
C13—C14	1.384 (4)	C23—H23	0.93
C14—C15	1.360 (5)	C24—H24	0.93
C15—C16	1.368 (5)	C25—H25	0.93
C16—C17	1.375 (4)	C26—H26	0.93
N1—Ag1—N1^i	180	C21—C20—C19	120.3 (3)
F2^ii—P1—F2	180.0 (2)	C20—C21—C22	121.0 (2)
F2^ii—P1—F1^ii	91.5 (2)	C21—C22—C27	120.2 (3)
F2—P1—F1^ii	88.5 (2)	C21—C22—C23	122.6 (3)
F2^ii—P1—F1	88.5 (2)	C27—C22—C23	117.2 (3)
F2—P1—F1	91.5 (2)	C24—C23—C22	122.4 (3)
F1^ii—P1—F1	180.0 (2)	C23—C24—C25	120.1 (3)
F2^ii—P1—F3	91.2 (1)	C26—C25—C24	120.5 (3)
F2—P1—F3	88.7 (1)	C25—C26—C27	121.2 (3)
F1^ii—P1—F3	88.3 (1)	C26—C27—C22	118.5 (2)
F1—P1—F3	91.7 (1)	C26—C27—C18	124.4 (2)
F2^ii—P1—F3^ii	88.7 (1)	C22—C27—C18	117.0 (2)
F2—P1—F3^ii	91.3 (1)	C11—N3—H3n	113.9
F1^ii—P1—F3^ii	91.7 (1)	C18—N3—H3n	113.9
F1—P1—F3^ii	88.3 (1)	C1—C2—H2	120.6
F3—P1—F3^ii	180	C3—C2—H2	120.6
C9—N1—N2	107.1 (2)	C4—C3—H3	119.6
C9—N1—Ag1	131.2 (2)	C2—C3—H3	119.6
N2—N1—Ag1	121.6 (1)	C5—C4—H4	120.0
C7—N2—N1	111.2 (2)	C3—C4—H4	120.0
C7—N2—C1	127.0 (2)	C4—C5—H5	119.8
N1—N2—C1	121.3 (2)	C6—C5—H5	119.8
C11—N3—C18	132.2 (2)	C1—C6—H6	120.4
C2—C1—C6	120.8 (2)	C5—C6—H6	120.4
C2—C1—N2	119.2 (2)	C9—C10—H10a	109.5
C6—C1—N2	119.9 (2)	C9—C10—H10b	109.5
C1—C2—C3	118.9 (2)	H10a—C10—H10b	109.5
C4—C3—C2	120.8 (3)	C9—C10—H10c	109.5
C5—C4—C3	120.1 (2)	H10a—C10—H10c	109.5
C4—C5—C6	120.3 (3)	H10b—C10—H10c	109.5
C1—C6—C5	119.1 (2)	C12—C13—H13	120.2
O1—C7—N2	125.0 (2)	C14—C13—H13	120.2
O1—C7—C8	129.6 (2)	C15—C14—H14	119.9
N2—C7—C8	105.3 (2)	C13—C14—H14	119.9
C11—C8—C9	132.2 (2)	C14—C15—H15	119.8
C11—C8—C7	122.1 (2)	C16—C15—H15	119.8
C9—C8—C7	105.6 (2)	C15—C16—H16	120.0
N1—C9—C8	110.8 (2)	C17—C16—H16	120.0
N1—C9—C10	119.7 (2)	C16—C17—H17	120.0
C8—C9—C10	129.6 (2)	C12—C17—H17	120.0
N3—C11—C8	116.6 (2)	C18—C19—H19	119.7
N3—C11—C12	120.8 (2)	C20—C19—H19	119.7
C8—C11—C12	122.5 (2)	C21—C20—H20	119.8
C13—C12—C17	119.7 (2)	C19—C20—H20	119.8
C13—C12—C11	118.9 (2)	C20—C21—H21	119.5
C17—C12—C11	121.3 (2)	C22—C21—H21	119.5
C12—C13—C14	119.6 (3)	C24—C23—H23	118.8
C15—C14—C13	120.2 (3)	C22—C23—H23	118.8
C14—C15—C16	120.5 (3)	C23—C24—H24	119.9
C15—C16—C17	120.0 (3)	C25—C24—H24	119.9
C16—C17—C12	120.0 (3)	C26—C25—H25	119.7
C19—C18—N3	123.5 (2)	C24—C25—H25	119.7
C19—C18—C27	120.7 (2)	C25—C26—H26	119.4
N3—C18—C27	115.8 (2)	C27—C26—H26	119.4
C18—C19—C20	120.6 (3)
C9—N1—N2—C7	0.5 (3)	C7—C8—C11—C12	−170.3 (2)
Ag1—N1—N2—C7	176.6 (2)	N3—C11—C12—C13	−76.8 (3)
C9—N1—N2—C1	173.2 (2)	C8—C11—C12—C13	98.6 (3)
Ag1—N1—N2—C1	−10.7 (3)	N3—C11—C12—C17	102.2 (3)
C7—N2—C1—C2	−51.2 (3)	C8—C11—C12—C17	−82.4 (3)
N1—N2—C1—C2	137.4 (2)	C17—C12—C13—C14	−0.8 (4)
C7—N2—C1—C6	126.2 (3)	C11—C12—C13—C14	178.2 (3)
N1—N2—C1—C6	−45.2 (3)	C12—C13—C14—C15	0.1 (5)
C6—C1—C2—C3	0.6 (4)	C13—C14—C15—C16	0.1 (6)
N2—C1—C2—C3	178.0 (2)	C14—C15—C16—C17	0.4 (6)
C1—C2—C3—C4	0.0 (4)	C15—C16—C17—C12	−1.0 (5)
C2—C3—C4—C5	0.6 (4)	C13—C12—C17—C16	1.3 (4)
C3—C4—C5—C6	−1.7 (4)	C11—C12—C17—C16	−177.7 (3)
C2—C1—C6—C5	−1.7 (4)	C11—N3—C18—C19	−27.2 (5)
N2—C1—C6—C5	−179.1 (2)	C11—N3—C18—C27	154.5 (3)
C4—C5—C6—C1	2.3 (4)	N3—C18—C19—C20	178.9 (3)
N1—N2—C7—O1	176.5 (2)	C27—C18—C19—C20	−2.8 (4)
C1—N2—C7—O1	4.4 (4)	C18—C19—C20—C21	0.8 (5)
N1—N2—C7—C8	−0.4 (3)	C19—C20—C21—C22	1.5 (5)
C1—N2—C7—C8	−172.6 (2)	C20—C21—C22—C27	−1.6 (5)
O1—C7—C8—C11	0.3 (4)	C20—C21—C22—C23	179.6 (3)
N2—C7—C8—C11	177.0 (2)	C21—C22—C23—C24	−179.0 (3)
O1—C7—C8—C9	−176.6 (3)	C27—C22—C23—C24	2.3 (5)
N2—C7—C8—C9	0.2 (3)	C22—C23—C24—C25	−0.4 (6)
N2—N1—C9—C8	−0.4 (3)	C23—C24—C25—C26	−1.9 (6)
Ag1—N1—C9—C8	−176.0 (2)	C24—C25—C26—C27	2.2 (5)
N2—N1—C9—C10	177.9 (2)	C25—C26—C27—C22	−0.2 (4)
Ag1—N1—C9—C10	2.3 (4)	C25—C26—C27—C18	179.4 (3)
C11—C8—C9—N1	−176.2 (3)	C21—C22—C27—C26	179.3 (3)
C7—C8—C9—N1	0.1 (3)	C23—C22—C27—C26	−1.9 (4)
C11—C8—C9—C10	5.7 (5)	C21—C22—C27—C18	−0.3 (4)
C7—C8—C9—C10	−177.9 (3)	C23—C22—C27—C18	178.5 (2)
C18—N3—C11—C8	−177.8 (3)	C19—C18—C27—C26	−177.0 (3)
C18—N3—C11—C12	−2.1 (4)	N3—C18—C27—C26	1.4 (4)
C9—C8—C11—N3	−178.8 (3)	C19—C18—C27—C22	2.6 (4)
C7—C8—C11—N3	5.3 (4)	N3—C18—C27—C22	−179.0 (2)
C9—C8—C11—C12	5.6 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3n···O1	0.86	1.92	2.669 (2)	145