Crystal structure of a helical silver(I) coordination polymer based on an unsymmetrical dipyridyl ligand: catena-poly[[silver(I)-μ-N-(pyridin-4-ylmeth­yl)pyridine-3-amine-κ2N:N′] tetra­fluorido­borate methanol hemisolvate]

Moon, S.-H.; Kang, Y.; Park, K.-M.

doi:10.1107/S205698901501837X

Crystal structure of a helical silver(I) coordination polymer based on an unsymmetrical dipyridyl ligand: catena-poly[[silver(I)-μ-N-(pyridin-4-ylmethyl)pyridine-3-amine-κ²N:N′] tetrafluoridoborate methanol hemisolvate]

The reaction of AgBF₄ with the unsymmetrical ligand N-(pyridin-4-ylmethyl)pyridine-3-amine afforded a helical coordination polymer. The Ag^I atom adopts a slightly distorted linear coordination geometry. The symmetry-related right- and left-handed helical chains are arranged alternately via Ag

Ag and Ag

F interactions and π–π stacking interactions, resulting in the formation of a two-dimensional supramolecular network.

Keywords: crystal structure; silver(I) tetrafluoridoborate; unsymmetrical dipyridyl ligand; helical coordination polymer.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S205698901501837X/cv5498sup1.cif Contains datablocks I, New_Global_Publ_Block
	Structure factor file (CIF format) https://doi.org/10.1107/S205698901501837X/cv5498Isup2.hkl Contains datablock I

CCDC reference: 1428966

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.011 Å
Disorder in solvent or counterion
R factor = 0.053
wR factor = 0.167
Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       *O12    -  *H12    ..     Please Check

Alert level C
PLAT234_ALERT_4_C Large Hirshfeld Difference F3B    --  B1      ..       0.25 Ang.
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors of          B1 Check
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0107 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2     ..  F2B     ..       2.58 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C11 H11 Ag N3
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -2.874 Report
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          4 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          8 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          4 Report
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          2 Info
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT045_ALERT_1_G Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT Unusually Large.       0.10 Report
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          1 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT231_ALERT_4_G Hirshfeld Test (Solvent)   F1A    --  B1      ..        5.7 su
PLAT231_ALERT_4_G Hirshfeld Test (Solvent)   F1B    --  B1      ..        5.2 su
PLAT300_ALERT_4_G Atom Site Occupancy of *O12    is Constrained at      0.500 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H12    is Constrained at      0.500 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *C12    is Constrained at      0.500 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H12A   is Constrained at      0.500 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H12B   is Constrained at      0.500 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H12C   is Constrained at      0.500 Check
PLAT302_ALERT_4_G Anion/Solvent Disorder ............ Percentage =         83 Note
PLAT432_ALERT_2_G Short Inter X...Y Contact  F3B    ..  C4      ..       2.94 Ang.
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1 Do !
            N3  -AG1 -N1  -C1    -87.00  2.00   2.646   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          3 Do !
            N3  -AG1 -N1  -C5     86.00  2.00   2.646   1.555   1.555   1.555
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #         18 Check
              F1A  -B1   -F1B     1.555   1.555   1.555              8.00 Deg.
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         31 Note
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...          1 Check

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

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

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

catena-Poly[[silver(I)-µ-N-(pyridine-4-ylmethyl)pyridine-3-amine-κ²N:N'] tetrafluoridoborate methanol hemisolvate] top

Crystal data top

[Ag(C₁₁H₁₁N₃)](BF₄)·0.5CH₄O	F(000) = 780
M_r = 395.93	D_x = 1.834 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2696 reflections
a = 9.2597 (8) Å	θ = 2.4–24.7°
b = 15.6485 (14) Å	µ = 1.45 mm⁻¹
c = 10.3574 (10) Å	T = 173 K
β = 107.185 (2)°	Block, colorless
V = 1433.8 (2) Å³	0.50 × 0.40 × 0.40 mm
Z = 4

Data collection top

Bruker SMART CCD area detector diffractometer	2821 independent reflections
Radiation source: fine-focus sealed tube	1883 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
φ and ω scans	θ_max = 26.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→11
T_min = 0.531, T_max = 0.595	k = −17→19
8014 measured reflections	l = −10→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.1027P)²] where P = (F_o² + 2F_c²)/3
2821 reflections	(Δ/σ)_max = 0.001
227 parameters	Δρ_max = 1.18 e Å⁻³
31 restraints	Δρ_min = −0.70 e Å⁻³

Special details top

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.

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 > 2sigma(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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ag1	0.67175 (6)	−0.04405 (3)	0.54637 (6)	0.0593 (3)
B1	0.6447 (9)	0.1230 (5)	0.8147 (8)	0.077 (3)
F1A	0.733 (3)	0.0831 (17)	0.751 (3)	0.217 (10)	0.669 (13)
F2A	0.7295 (8)	0.1786 (5)	0.9050 (9)	0.094 (3)	0.669 (13)
F3A	0.6034 (13)	0.0671 (7)	0.9030 (10)	0.127 (4)	0.669 (13)
F4A	0.5186 (12)	0.1597 (13)	0.7407 (16)	0.197 (8)	0.669 (13)
F1B	0.735 (2)	0.0733 (11)	0.762 (2)	0.072 (5)	0.331 (13)
F2B	0.6706 (19)	0.2035 (7)	0.7697 (18)	0.095 (6)	0.331 (13)
F3B	0.680 (3)	0.1190 (19)	0.9487 (12)	0.143 (9)	0.331 (13)
F4B	0.533 (2)	0.0941 (12)	0.7100 (13)	0.103 (8)	0.331 (13)
N1	0.7799 (6)	0.0402 (3)	0.4442 (6)	0.0510 (13)
N2	1.1086 (8)	0.1806 (4)	0.5210 (8)	0.0774 (19)
H2	1.1636	0.2066	0.4765	0.093*
N3	0.9214 (6)	0.3630 (3)	0.8522 (6)	0.0556 (13)
C1	0.8958 (7)	0.0881 (4)	0.5113 (7)	0.0515 (15)
H1	0.9210	0.0901	0.6071	0.062*
C2	0.9820 (7)	0.1356 (4)	0.4482 (7)	0.0554 (16)
C3	0.9445 (10)	0.1342 (5)	0.3107 (8)	0.070 (2)
H3	1.0018	0.1660	0.2650	0.083*
C4	0.8219 (11)	0.0860 (5)	0.2380 (8)	0.077 (2)
H4	0.7934	0.0851	0.1420	0.092*
C5	0.7414 (9)	0.0390 (4)	0.3067 (8)	0.0639 (19)
H5	0.6580	0.0053	0.2572	0.077*
C6	1.1541 (8)	0.1869 (4)	0.6647 (10)	0.071 (2)
H6A	1.2613	0.2049	0.6947	0.085*
H6B	1.1491	0.1290	0.7015	0.085*
C7	1.0659 (7)	0.2468 (4)	0.7280 (8)	0.0576 (17)
C8	0.9678 (8)	0.3085 (4)	0.6527 (8)	0.0617 (18)
H8	0.9486	0.3119	0.5576	0.074*
C9	0.8995 (7)	0.3642 (4)	0.7187 (8)	0.0585 (17)
H9	0.8329	0.4059	0.6666	0.070*
C10	1.0124 (8)	0.3026 (4)	0.9239 (8)	0.0656 (19)
H10	1.0274	0.2992	1.0186	0.079*
C11	1.0858 (8)	0.2446 (4)	0.8627 (8)	0.0621 (18)
H11	1.1509	0.2028	0.9165	0.074*
C12	1.022 (2)	0.0409 (10)	0.980 (3)	0.256 (12)	0.50
H12A	1.0264	0.0829	1.0514	0.385*	0.50
H12B	0.9477	0.0594	0.8961	0.385*	0.50
H12C	1.1217	0.0362	0.9658	0.385*	0.50
O12	1.022 (2)	0.0409 (10)	0.980 (3)	0.256 (12)	0.50
H12	1.1101	0.0377	0.9735	0.385*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0566 (4)	0.0409 (3)	0.0845 (5)	0.0059 (2)	0.0271 (3)	0.0069 (2)
B1	0.081 (6)	0.077 (6)	0.064 (6)	−0.011 (5)	0.010 (5)	−0.004 (5)
F1A	0.237 (13)	0.226 (13)	0.203 (13)	0.004 (9)	0.088 (9)	−0.034 (9)
F2A	0.090 (5)	0.079 (5)	0.120 (8)	−0.025 (4)	0.043 (5)	−0.053 (5)
F3A	0.138 (9)	0.147 (9)	0.090 (7)	−0.053 (7)	0.026 (6)	−0.008 (6)
F4A	0.102 (9)	0.28 (2)	0.173 (12)	0.070 (12)	−0.014 (8)	0.009 (14)
F1B	0.112 (9)	0.053 (7)	0.066 (7)	−0.005 (6)	0.050 (6)	−0.034 (5)
F2B	0.108 (10)	0.057 (7)	0.113 (10)	−0.006 (6)	0.022 (7)	−0.013 (6)
F3B	0.148 (12)	0.155 (13)	0.125 (11)	0.010 (9)	0.037 (9)	−0.024 (9)
F4B	0.154 (19)	0.090 (12)	0.057 (9)	−0.039 (12)	0.015 (10)	−0.029 (8)
N1	0.049 (3)	0.035 (3)	0.069 (4)	0.007 (2)	0.018 (3)	0.001 (2)
N2	0.074 (4)	0.048 (3)	0.127 (6)	0.000 (3)	0.054 (4)	−0.002 (4)
N3	0.051 (3)	0.038 (3)	0.078 (4)	−0.004 (2)	0.018 (3)	−0.004 (3)
C1	0.057 (4)	0.038 (3)	0.062 (4)	0.013 (3)	0.022 (3)	−0.001 (3)
C2	0.058 (4)	0.035 (3)	0.081 (5)	0.011 (3)	0.032 (4)	0.003 (3)
C3	0.092 (6)	0.049 (4)	0.079 (5)	0.025 (4)	0.042 (4)	0.021 (4)
C4	0.115 (7)	0.061 (5)	0.060 (5)	0.025 (5)	0.034 (5)	0.013 (4)
C5	0.073 (5)	0.047 (4)	0.067 (5)	0.015 (3)	0.014 (4)	−0.003 (3)
C6	0.051 (4)	0.045 (4)	0.111 (7)	0.006 (3)	0.014 (4)	−0.019 (4)
C7	0.046 (3)	0.036 (3)	0.085 (5)	−0.004 (3)	0.011 (3)	−0.001 (3)
C8	0.056 (4)	0.048 (4)	0.074 (5)	0.013 (3)	0.009 (3)	−0.008 (3)
C9	0.047 (3)	0.044 (3)	0.078 (5)	0.006 (3)	0.011 (3)	0.001 (3)
C10	0.072 (4)	0.042 (4)	0.074 (5)	−0.008 (3)	0.008 (4)	0.010 (3)
C11	0.054 (4)	0.035 (3)	0.092 (6)	0.002 (3)	0.013 (4)	0.008 (3)
C12	0.145 (14)	0.29 (3)	0.36 (3)	−0.016 (16)	0.106 (15)	−0.01 (2)
O12	0.145 (14)	0.29 (3)	0.36 (3)	−0.016 (16)	0.106 (15)	−0.01 (2)

Geometric parameters (Å, º) top

Ag1—N1	2.118 (5)	C2—C3	1.362 (11)
Ag1—N3ⁱ	2.121 (5)	C3—C4	1.386 (12)
Ag1—Ag1ⁱⁱ	3.3369 (10)	C3—H3	0.9500
B1—F4A	1.324 (8)	C4—C5	1.384 (11)
B1—F3B	1.330 (10)	C4—H4	0.9500
B1—F4B	1.336 (9)	C5—H5	0.9500
B1—F2A	1.348 (11)	C6—C7	1.514 (9)
B1—F1A	1.349 (10)	C6—H6A	0.9900
B1—F1B	1.367 (9)	C6—H6B	0.9900
B1—F2B	1.388 (9)	C7—C11	1.352 (10)
B1—F3A	1.398 (8)	C7—C8	1.396 (9)
N1—C1	1.325 (9)	C8—C9	1.371 (10)
N1—C5	1.363 (10)	C8—H8	0.9500
N2—C2	1.385 (9)	C9—H9	0.9500
N2—C6	1.425 (11)	C10—C11	1.394 (10)
N2—H2	0.8800	C10—H10	0.9500
N3—C10	1.336 (8)	C11—H11	0.9500
N3—C9	1.337 (9)	C12—C12^iv	1.44 (3)
N3—Ag1ⁱⁱⁱ	2.121 (5)	C12—H12A	0.9800
C1—C2	1.388 (9)	C12—H12B	0.9800
C1—H1	0.9500	C12—H12C	0.9800

N1—Ag1—N3ⁱ	174.70 (19)	N1—C1—H1	118.5
N1—Ag1—Ag1ⁱⁱ	98.63 (14)	C2—C1—H1	118.5
N3ⁱ—Ag1—Ag1ⁱⁱ	86.18 (14)	C3—C2—N2	119.4 (7)
F4A—B1—F3B	121.9 (14)	C3—C2—C1	118.6 (7)
F4A—B1—F4B	48.5 (9)	N2—C2—C1	121.9 (7)
F3B—B1—F4B	136.5 (18)	C2—C3—C4	119.5 (7)
F4A—B1—F2A	110.8 (11)	C2—C3—H3	120.3
F3B—B1—F2A	52.5 (14)	C4—C3—H3	120.3
F4B—B1—F2A	159.0 (12)	C5—C4—C3	119.3 (7)
F4A—B1—F1A	118.5 (16)	C5—C4—H4	120.4
F3B—B1—F1A	119.4 (17)	C3—C4—H4	120.4
F4B—B1—F1A	83.3 (16)	N1—C5—C4	121.0 (7)
F2A—B1—F1A	109.0 (14)	N1—C5—H5	119.5
F4A—B1—F1B	123.6 (14)	C4—C5—H5	119.5
F3B—B1—F1B	113.5 (15)	N2—C6—C7	117.7 (6)
F4B—B1—F1B	84.3 (15)	N2—C6—H6A	107.9
F2A—B1—F1B	110.2 (10)	C7—C6—H6A	107.9
F1A—B1—F1B	8 (2)	N2—C6—H6B	107.9
F4A—B1—F2B	67.8 (10)	C7—C6—H6B	107.9
F3B—B1—F2B	112.2 (17)	H6A—C6—H6B	107.2
F4B—B1—F2B	101.7 (11)	C11—C7—C8	117.5 (7)
F2A—B1—F2B	61.5 (9)	C11—C7—C6	120.3 (6)
F1A—B1—F2B	93.7 (15)	C8—C7—C6	122.1 (8)
F1B—B1—F2B	101.3 (12)	C9—C8—C7	118.7 (7)
F4A—B1—F3A	106.6 (11)	C9—C8—H8	120.6
F3B—B1—F3A	47.1 (14)	C7—C8—H8	120.6
F4B—B1—F3A	91.4 (10)	N3—C9—C8	123.8 (6)
F2A—B1—F3A	99.5 (7)	N3—C9—H9	118.1
F1A—B1—F3A	110.8 (14)	C8—C9—H9	118.1
F1B—B1—F3A	102.9 (12)	N3—C10—C11	121.3 (7)
F2B—B1—F3A	153.5 (11)	N3—C10—H10	119.3
C1—N1—C5	118.6 (6)	C11—C10—H10	119.3
C1—N1—Ag1	121.3 (5)	C7—C11—C10	121.1 (6)
C5—N1—Ag1	119.8 (5)	C7—C11—H11	119.5
C2—N2—C6	123.0 (6)	C10—C11—H11	119.5
C2—N2—H2	118.5	C12^iv—C12—H12A	109.5
C6—N2—H2	118.5	C12^iv—C12—H12B	109.5
C10—N3—C9	117.5 (6)	H12A—C12—H12B	109.5
C10—N3—Ag1ⁱⁱⁱ	119.4 (5)	C12^iv—C12—H12C	109.5
C9—N3—Ag1ⁱⁱⁱ	122.9 (4)	H12A—C12—H12C	109.5
N1—C1—C2	123.0 (7)	H12B—C12—H12C	109.5

N3ⁱ—Ag1—N1—C1	−87 (2)	C3—C4—C5—N1	0.7 (10)
Ag1ⁱⁱ—Ag1—N1—C1	117.9 (4)	C2—N2—C6—C7	−75.9 (9)
N3ⁱ—Ag1—N1—C5	86 (2)	N2—C6—C7—C11	168.5 (6)
Ag1ⁱⁱ—Ag1—N1—C5	−69.4 (5)	N2—C6—C7—C8	−14.7 (10)
C5—N1—C1—C2	−1.5 (9)	C11—C7—C8—C9	1.2 (10)
Ag1—N1—C1—C2	171.4 (4)	C6—C7—C8—C9	−175.7 (6)
C6—N2—C2—C3	178.6 (6)	C10—N3—C9—C8	−1.6 (10)
C6—N2—C2—C1	−4.6 (10)	Ag1ⁱⁱⁱ—N3—C9—C8	175.0 (5)
N1—C1—C2—C3	1.2 (9)	C7—C8—C9—N3	0.0 (10)
N1—C1—C2—N2	−175.6 (6)	C9—N3—C10—C11	2.0 (9)
N2—C2—C3—C4	177.0 (6)	Ag1ⁱⁱⁱ—N3—C10—C11	−174.7 (5)
C1—C2—C3—C4	0.2 (10)	C8—C7—C11—C10	−0.8 (10)
C2—C3—C4—C5	−1.0 (11)	C6—C7—C11—C10	176.1 (6)
C1—N1—C5—C4	0.6 (9)	N3—C10—C11—C7	−0.8 (10)
Ag1—N1—C5—C4	−172.4 (5)

Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) −x+1, −y, −z+1; (iii) −x+3/2, y+1/2, −z+3/2; (iv) −x+2, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···F2A^v	0.88	2.10	2.887 (9)	148
N2—H2···F2B^v	0.88	2.58	3.357 (17)	148
C6—H6A···F4A^vi	0.99	2.39	3.259 (12)	146
C10—H10···F4A^vii	0.95	2.41	3.318 (19)	159
C12—H12B···F1A	0.98	2.14	3.08 (4)	160

Symmetry codes: (v) x+1/2, −y+1/2, z−1/2; (vi) x+1, y, z; (vii) x+1/2, −y+1/2, z+1/2.

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Crystal structure of a helical silver(I) coordination polymer based on an unsymmetrical dipyridyl ligand: catena-poly[[silver(I)-μ-N-(pyridin-4-ylmeth­yl)pyridine-3-amine-κ2N:N′] tetra­fluorido­borate methanol hemisolvate]

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Crystal structure of a helical silver(I) coordination polymer based on an unsymmetrical dipyridyl ligand: catena-poly[[silver(I)-μ-N-(pyridin-4-ylmethyl)pyridine-3-amine-κ²N:N′] tetrafluoridoborate methanol hemisolvate]