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In the title compound, [AgCl(C12H8N2)]n, the Ag atom is four-coordinate in a highly distorted tetrahedral environment formed by two N atoms of phenanthroline and two Cl atoms. The Ag atoms are bridged by Cl atoms and the compound forms a one-dimensional polymer. Ag and Cl atoms lie on twofold rotation axes.
Supporting information
CCDC reference: 252950
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.010 Å
- R factor = 0.036
- wR factor = 0.066
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
Alert level B
ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
Tmin and Tmax reported: 0.456 0.810
Tmin' and Tmax expected: 0.805 0.809
RR' = 0.566
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.56
Alert level C
STRVA01_ALERT_4_C Flack test results are ambiguous.
From the CIF: _refine_ls_abs_structure_Flack 0.530
From the CIF: _refine_ls_abs_structure_Flack_su 0.060
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.53
PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 531.70 Ang-3
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. CL1 .. 2.88 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 .. CL1 .. 2.96 Ang.
PLAT731_ALERT_1_C Bond Calc 2.535(3), Rep 2.5350(10) ...... 3.00 su-Rat
AG1 -CL1 1.555 1.556
PLAT731_ALERT_1_C Bond Calc 2.535(3), Rep 2.5350(10) ...... 3.00 su-Rat
CL1 -AG1 1.555 1.554
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.40
From the CIF: _reflns_number_total 1215
Count of symmetry unique reflns 651
Completeness (_total/calc) 186.64%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 564
Fraction of Friedel pairs measured 0.866
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku/MSC, 2004); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004) and CRYSTALS (Watkin et al., 1996); program(s) used to solve structure: SIR97 (Altomare et al., 1999) and DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1996); software used to prepare material for publication: CrystalStructure.
Crystal data top
[AgCl(C12H8N2)] | F(000) = 316.00 |
Mr = 323.52 | Dx = 2.020 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: c_2y | Cell parameters from 2250 reflections |
a = 12.566 (14) Å | θ = 3.4–27.4° |
b = 10.235 (11) Å | µ = 2.11 mm−1 |
c = 4.279 (4) Å | T = 296 K |
β = 104.92 (4)° | Prism, red |
V = 531.7 (8) Å3 | 0.10 × 0.10 × 0.10 mm |
Z = 2 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 686 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.043 |
ω scans | θmax = 27.4° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −16→16 |
Tmin = 0.456, Tmax = 0.810 | k = −13→13 |
2616 measured reflections | l = −5→5 |
1215 independent reflections | |
Refinement top
Refinement on F2 | w = 1/[σ2(Fo2) + (0.0268P)2] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.036 | (Δ/σ)max < 0.001 |
wR(F2) = 0.066 | Δρmax = 0.41 e Å−3 |
S = 0.89 | Δρmin = −0.52 e Å−3 |
1215 reflections | Absolute structure: Flack (1983), 564 Friedel pairs [CHECK?] |
75 parameters | Absolute structure parameter: 0.53 (6) |
All H-atom parameters refined | |
Special details top
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using all reflections. The weighted R-factor (wR),
goodness of fit (S) and R-factor (gt) are based on F,
with F set to zero for negative F. The threshold expression of
F2 > 2.0 σ(F2) is used only for calculating R-factor
(gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Ag1 | 0.5000 | 0.50819 (6) | 0.0000 | 0.0562 (2) | |
Cl1 | 0.5000 | 0.6411 (2) | −0.5000 | 0.0530 (6) | |
N1 | 0.4093 (4) | 0.3159 (4) | 0.120 (1) | 0.041 (1) | |
C1 | 0.3237 (5) | 0.3159 (6) | 0.247 (1) | 0.053 (2) | |
C2 | 0.2735 (6) | 0.2023 (8) | 0.318 (2) | 0.067 (2) | |
C3 | 0.3164 (6) | 0.0841 (7) | 0.260 (1) | 0.061 (2) | |
C4 | 0.4080 (6) | 0.0796 (6) | 0.132 (2) | 0.045 (2) | |
C5 | 0.4531 (4) | 0.1977 (5) | 0.064 (1) | 0.039 (1) | |
C6 | 0.4563 (6) | −0.0409 (6) | 0.067 (2) | 0.063 (3) | |
H1 | 0.2955 | 0.3959 | 0.2907 | 0.064* | |
H2 | 0.2125 | 0.2064 | 0.4036 | 0.081* | |
H3 | 0.2844 | 0.0068 | 0.3049 | 0.074* | |
H6 | 0.4277 | −0.1198 | 0.1161 | 0.075* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ag1 | 0.0726 (5) | 0.0397 (3) | 0.0601 (4) | 0.0000 | 0.0239 (3) | 0.0000 |
Cl1 | 0.084 (2) | 0.037 (1) | 0.047 (1) | 0.0000 | 0.032 (1) | 0.0000 |
N1 | 0.043 (3) | 0.043 (3) | 0.040 (3) | 0.002 (2) | 0.014 (2) | 0.001 (2) |
C1 | 0.053 (4) | 0.064 (4) | 0.043 (3) | 0.010 (3) | 0.014 (3) | 0.002 (3) |
C2 | 0.046 (4) | 0.107 (6) | 0.049 (4) | −0.017 (4) | 0.013 (3) | 0.000 (4) |
C3 | 0.063 (5) | 0.074 (4) | 0.040 (3) | −0.034 (4) | 0.001 (3) | 0.011 (3) |
C4 | 0.053 (5) | 0.041 (4) | 0.035 (3) | −0.014 (3) | 0.000 (3) | 0.009 (3) |
C5 | 0.048 (4) | 0.037 (3) | 0.027 (3) | −0.004 (2) | 0.001 (3) | 0.003 (2) |
C6 | 0.081 (8) | 0.035 (3) | 0.053 (5) | −0.008 (3) | −0.016 (4) | 0.012 (3) |
Geometric parameters (Å, º) top
Ag1—Cl1 | 2.535 (3) | C2—C3 | 1.37 (1) |
Ag1—Cl1i | 2.535 (1) | C2—H2 | 0.9300 |
Ag1—N1 | 2.396 (5) | C3—C4 | 1.40 (1) |
Ag1—N1ii | 2.396 (5) | C3—H3 | 0.9300 |
Cl1—Ag1iii | 2.535 (1) | C4—C5 | 1.397 (9) |
N1—C1 | 1.323 (9) | C4—C6 | 1.43 (1) |
N1—C5 | 1.376 (7) | C5—C5ii | 1.423 (8) |
C1—C2 | 1.39 (1) | C6—C6ii | 1.36 (1) |
C1—H1 | 0.9300 | C6—H6 | 0.9300 |
| | | |
Ag1···C1 | 3.333 (7) | C4···C4ix | 3.394 (8) |
Ag1···C1ii | 3.333 (7) | C4···C5ii | 2.44 (1) |
Ag1···C5 | 3.257 (5) | C4···C6ii | 2.43 (1) |
Ag1···C5ii | 3.257 (5) | C4···H1xi | 3.3110 |
Ag1···H1 | 3.3344 | C4···H2 | 3.2463 |
Ag1···H1ii | 3.3344 | C4···H3iii | 3.5584 |
Ag1···H2iv | 3.4428 | C4···H3 | 2.0261 |
Ag1···H2v | 3.4428 | C4···H6 | 2.0585 |
Ag1···H3iv | 3.4748 | C4···H6ii | 3.2685 |
Ag1···H3v | 3.4748 | C5···N1ii | 2.405 (8) |
Cl1···H1iii | 3.5384 | C5···C2iii | 3.403 (7) |
Cl1···H1ii | 3.5384 | C5···C4ii | 2.44 (1) |
Cl1···H2vi | 2.8834 | C5···C6 | 2.442 (8) |
Cl1···H2v | 2.8834 | C5···C6ii | 2.811 (9) |
Cl1···H6vii | 2.9570 | C5···H1 | 3.1566 |
Cl1···H6viii | 2.9570 | C5···H2iii | 3.5703 |
N1···N1ii | 2.733 (8) | C5···H3 | 3.2395 |
N1···N1ix | 3.455 (6) | C5···H6 | 3.2778 |
N1···C2 | 2.394 (9) | C6···C4ii | 2.43 (1) |
N1···C3 | 2.776 (8) | C6···C5ii | 2.811 (9) |
N1···C4 | 2.420 (8) | C6···C6ix | 3.59 (1) |
N1···C5ii | 2.405 (8) | C6···H1xi | 3.2061 |
N1···H1iii | 3.5644 | C6···H3iii | 3.4506 |
N1···H1 | 1.9446 | C6···H3 | 2.6601 |
N1···H2iii | 3.5883 | C6···H6ii | 1.9945 |
N1···H2 | 3.2225 | C6···H6ix | 3.5184 |
N1···H3v | 3.2821 | H1···Cl1i | 3.5384 |
C1···C3 | 2.375 (9) | H1···N1i | 3.5644 |
C1···C4 | 2.735 (9) | H1···C3v | 3.0867 |
C1···C5 | 2.318 (9) | H1···C3x | 3.2840 |
C1···H2 | 2.0345 | H1···C4v | 3.3110 |
C1···H3 | 3.2206 | H1···C6v | 3.2061 |
C1···H3v | 3.0969 | H2···Ag1xiii | 3.4428 |
C1···H3x | 3.2680 | H2···Cl1xiv | 2.8834 |
C1···H6v | 3.2093 | H2···N1i | 3.5883 |
C2···C4 | 2.40 (1) | H2···C5i | 3.5703 |
C2···C5 | 2.75 (1) | H3···Ag1xiii | 3.4748 |
C2···C5i | 3.403 (7) | H3···N1xi | 3.2821 |
C2···H1 | 2.0087 | H3···C1xi | 3.0969 |
C2···H3 | 2.0068 | H3···C1xii | 3.2680 |
C2···H6v | 3.2777 | H3···C4i | 3.5584 |
C3···C5 | 2.396 (9) | H3···C6i | 3.4506 |
C3···C6 | 2.48 (1) | H6···Cl1xv | 2.9570 |
C3···H1 | 3.2078 | H6···C1xi | 3.2093 |
C3···H1xi | 3.0867 | H6···C2xi | 3.2777 |
C3···H1xii | 3.2840 | H6···C4ii | 3.2685 |
C3···H2 | 2.0165 | H6···C6ii | 1.9945 |
C3···H6 | 2.6698 | H6···C6ix | 3.5184 |
C4···C4ii | 2.82 (1) | | |
| | | |
Cl1—Ag1—Cl1i | 115.10 (5) | C3—C2—H2 | 120.8984 |
Cl1—Ag1—N1 | 136.5 (1) | H2—C2—C1 | 120.8981 |
Cl1—Ag1—N1ii | 99.0 (1) | C4—C3—C2 | 120.2 (7) |
Cl1i—Ag1—N1 | 99.0 (1) | C4—C3—H3 | 119.8908 |
Cl1i—Ag1—N1ii | 136.5 (1) | H3—C3—C2 | 119.8881 |
N1—Ag1—N1ii | 69.6 (2) | C5—C4—C3 | 118.2 (6) |
Ag1iii—Cl1—Ag1 | 115.10 (7) | C5—C4—C6 | 119.3 (7) |
C1—N1—Ag1 | 124.8 (4) | C6—C4—C3 | 122.6 (7) |
C1—N1—C5 | 118.4 (5) | C5ii—C5—N1 | 118.4 (5) |
C5—N1—Ag1 | 116.8 (4) | C5ii—C5—C4 | 120.1 (5) |
C2—C1—N1 | 123.5 (6) | C6ii—C6—C4 | 120.6 (6) |
C2—C1—H1 | 118.2479 | C6ii—C6—H6 | 119.6858 |
H1—C1—N1 | 118.2521 | H6—C6—C4 | 119.6841 |
C3—C2—C1 | 118.2 (7) | | |
| | | |
Cl1—Ag1—N1—C1 | −101.2 (4) | C1—C2—C3—C4 | 0.1 (7) |
Ag1—N1—C1—C2 | −179.1 (4) | C2—C3—C4—C5 | −0.6 (8) |
Ag1—N1—C5—C4 | 178.8 (4) | C3—C4—C5—N1 | −0.1 (6) |
N1—C1—C2—C3 | 1.2 (9) | C3—C4—C6—H6 | −1.9 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, y, −z; (iii) x, y, z−1; (iv) x+1/2, y+1/2, z; (v) −x+1/2, y+1/2, −z; (vi) x+1/2, y+1/2, z−1; (vii) x, y+1, z−1; (viii) −x+1, y+1, −z; (ix) −x+1, y, −z+1; (x) −x+1/2, y+1/2, −z+1; (xi) −x+1/2, y−1/2, −z; (xii) −x+1/2, y−1/2, −z+1; (xiii) x−1/2, y−1/2, z; (xiv) x−1/2, y−1/2, z+1; (xv) x, y−1, z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···Cl1xiv | 0.93 | 2.88 | 3.765 (8) | 159 |
C6—H6···Cl1xv | 0.93 | 2.96 | 3.716 (7) | 140 |
Symmetry codes: (xiv) x−1/2, y−1/2, z+1; (xv) x, y−1, z+1. |
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