The title compound, C
7H
7I
2NO
2+·I
−·C
7H
6I
2NO
2, crystallizes with
Z′ =
; the iodide anion lies on a twofold axis, and in the cation/zwitterion adduct the acidic H atom is disordered over an inversion centre. The residues are linked to form zigzag chains in the overall direction [103] by I
I interactions between anion and cation, and by classical O—H
O hydrogen bonds. Weak hydrogen bonds C—H
O link the chains to form layers parallel to (30
).
Supporting information
CCDC reference: 270234
Key indicators
- Single-crystal X-ray study
- T = 133 K
- Mean (C-C) = 0.005 Å
- R factor = 0.029
- wR factor = 0.052
- Data-to-parameter ratio = 24.3
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT431_ALERT_2_A Short Inter HL..A Contact I1 .. I2 .. 3.44 Ang.
| Author Response: We know about this contact and it is discussed in the
Comment section!!
|
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT128_ALERT_4_C Non-standard setting of Space group P2/c .... P2/n
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. I2 .. 3.26 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 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
0 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.
(3-Iodo-1-pyridinio)acetate–iodide–1-carboxymethyl-3-iodo-1-pyridinium–
(1:1:1)
top
Crystal data top
C7H7INO2+·I−·C7H6INO2 | F(000) = 604 |
Mr = 653.96 | Dx = 2.383 Mg m−3 |
Monoclinic, P2/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.9984 (8) Å | Cell parameters from 4228 reflections |
b = 6.3486 (4) Å | θ = 2–30.5° |
c = 13.2439 (12) Å | µ = 5.16 mm−1 |
β = 99.768 (4)° | T = 133 K |
V = 911.34 (12) Å3 | Prism, colourless |
Z = 2 | 0.11 × 0.05 × 0.05 mm |
Data collection top
Bruker SMART 1000 CCD diffractometer | 2648 independent reflections |
Radiation source: fine-focus sealed tube | 2049 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
Detector resolution: 8.192 pixels mm-1 | θmax = 30.0°, θmin = 2.2° |
ω and φ scans | h = −15→15 |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | k = −8→8 |
Tmin = 0.622, Tmax = 0.772 | l = −18→18 |
11241 measured reflections | |
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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0229P)2] where P = (Fo2 + 2Fc2)/3 |
2648 reflections | (Δ/σ)max = 0.001 |
109 parameters | Δρmax = 0.92 e Å−3 |
9 restraints | Δρmin = −1.03 e Å−3 |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C2 | 0.4370 (3) | 0.3943 (5) | 0.6707 (2) | 0.0210 (7) | |
H2 | 0.4709 | 0.2563 | 0.6747 | 0.025* | |
C3 | 0.3677 (3) | 0.4643 (5) | 0.5800 (2) | 0.0205 (7) | |
C4 | 0.3202 (3) | 0.6687 (5) | 0.5741 (3) | 0.0235 (7) | |
H4 | 0.2721 | 0.7189 | 0.5124 | 0.028* | |
C5 | 0.3444 (3) | 0.7981 (5) | 0.6602 (3) | 0.0259 (8) | |
H5 | 0.3146 | 0.9388 | 0.6572 | 0.031* | |
C6 | 0.4123 (3) | 0.7205 (5) | 0.7504 (3) | 0.0236 (8) | |
H6 | 0.4276 | 0.8072 | 0.8096 | 0.028* | |
N | 0.4567 (2) | 0.5220 (4) | 0.7540 (2) | 0.0200 (6) | |
I1 | 0.33110 (2) | 0.25643 (3) | 0.453928 (16) | 0.02159 (7) | |
C7 | 0.5269 (3) | 0.4397 (5) | 0.8513 (2) | 0.0229 (7) | |
H7A | 0.5320 | 0.5508 | 0.9043 | 0.027* | |
H7B | 0.6121 | 0.4066 | 0.8414 | 0.027* | |
C8 | 0.4686 (3) | 0.2401 (5) | 0.8901 (3) | 0.0218 (7) | |
O1 | 0.5290 (2) | 0.1794 (4) | 0.97633 (19) | 0.0262 (5) | |
H01 | 0.486 (6) | 0.082 (8) | 0.993 (7) | 0.05 (3)* | 0.50 |
O2 | 0.3781 (2) | 0.1579 (4) | 0.83885 (18) | 0.0268 (5) | |
I2 | 0.2500 | −0.08106 (5) | 0.2500 | 0.02636 (9) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.0189 (16) | 0.0187 (16) | 0.0248 (17) | −0.0012 (14) | 0.0019 (13) | −0.0027 (14) |
C3 | 0.0184 (16) | 0.0230 (18) | 0.0201 (17) | −0.0022 (13) | 0.0031 (13) | −0.0028 (14) |
C4 | 0.0219 (18) | 0.0241 (17) | 0.0240 (18) | −0.0021 (14) | 0.0027 (14) | 0.0051 (15) |
C5 | 0.030 (2) | 0.0158 (17) | 0.032 (2) | 0.0063 (14) | 0.0053 (16) | 0.0024 (14) |
C6 | 0.0273 (19) | 0.0140 (17) | 0.0301 (19) | 0.0010 (14) | 0.0068 (15) | −0.0028 (14) |
N | 0.0226 (14) | 0.0146 (14) | 0.0220 (15) | −0.0018 (11) | 0.0014 (12) | −0.0029 (11) |
I1 | 0.02342 (11) | 0.02121 (11) | 0.01901 (11) | 0.00053 (10) | 0.00033 (8) | −0.00001 (9) |
C7 | 0.0244 (17) | 0.0215 (17) | 0.0205 (17) | −0.0021 (15) | −0.0027 (13) | −0.0024 (14) |
C8 | 0.0243 (17) | 0.0164 (16) | 0.0241 (17) | 0.0035 (15) | 0.0020 (14) | −0.0110 (15) |
O1 | 0.0316 (15) | 0.0234 (12) | 0.0217 (13) | −0.0024 (12) | −0.0009 (11) | −0.0002 (11) |
O2 | 0.0278 (13) | 0.0254 (13) | 0.0253 (13) | −0.0050 (11) | −0.0013 (11) | −0.0012 (11) |
I2 | 0.03151 (18) | 0.02557 (17) | 0.02090 (16) | 0.000 | 0.00129 (13) | 0.000 |
Geometric parameters (Å, º) top
I2—I1i | 3.4443 (4) | C6—N | 1.349 (4) |
C2—N | 1.356 (4) | C6—H6 | 0.9500 |
C2—C3 | 1.382 (4) | N—C7 | 1.481 (4) |
C2—H2 | 0.9500 | C7—C8 | 1.547 (5) |
C3—C4 | 1.396 (4) | C7—H7A | 0.9900 |
C3—I1 | 2.112 (3) | C7—H7B | 0.9900 |
C4—C5 | 1.394 (5) | C8—O2 | 1.222 (4) |
C4—H4 | 0.9500 | C8—O1 | 1.280 (4) |
C5—C6 | 1.387 (5) | O1—H01 | 0.83 (2) |
C5—H5 | 0.9500 | | |
| | | |
I1—I2—I1i | 103.066 (13) | C5—C6—H6 | 120.0 |
N—C2—C3 | 120.2 (3) | C6—N—C2 | 121.5 (3) |
N—C2—H2 | 119.9 | C6—N—C7 | 119.5 (3) |
C3—C2—H2 | 119.9 | C2—N—C7 | 119.0 (3) |
C2—C3—C4 | 119.5 (3) | N—C7—C8 | 113.1 (3) |
C2—C3—I1 | 119.3 (2) | N—C7—H7A | 108.9 |
C4—C3—I1 | 121.2 (2) | C8—C7—H7A | 108.9 |
C5—C4—C3 | 119.0 (3) | N—C7—H7B | 108.9 |
C5—C4—H4 | 120.5 | C8—C7—H7B | 108.9 |
C3—C4—H4 | 120.5 | H7A—C7—H7B | 107.8 |
C6—C5—C4 | 119.7 (3) | O2—C8—O1 | 128.1 (3) |
C6—C5—H5 | 120.2 | O2—C8—C7 | 120.7 (3) |
C4—C5—H5 | 120.2 | O1—C8—C7 | 111.2 (3) |
N—C6—C5 | 120.1 (3) | C8—O1—H01 | 103 (7) |
N—C6—H6 | 120.0 | | |
| | | |
N—C2—C3—C4 | 1.3 (5) | C5—C6—N—C7 | −178.8 (3) |
N—C2—C3—I1 | −176.9 (2) | C3—C2—N—C6 | −1.5 (5) |
C2—C3—C4—C5 | 0.3 (5) | C3—C2—N—C7 | 177.5 (3) |
I1—C3—C4—C5 | 178.4 (2) | C6—N—C7—C8 | 121.3 (3) |
C3—C4—C5—C6 | −1.5 (5) | C2—N—C7—C8 | −57.8 (4) |
C4—C5—C6—N | 1.3 (5) | N—C7—C8—O2 | 4.4 (4) |
C5—C6—N—C2 | 0.2 (5) | N—C7—C8—O1 | −177.3 (3) |
Symmetry code: (i) −x+1/2, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H01···O1ii | 0.83 (2) | 1.73 (4) | 2.474 (5) | 150 (8) |
C7—H7A···O1iii | 0.99 | 2.50 | 3.451 (4) | 162 |
C5—H5···O2iv | 0.95 | 2.54 | 3.349 (4) | 143 |
C6—H6···O2v | 0.95 | 2.34 | 3.062 (4) | 132 |
C2—H2···I2vi | 0.95 | 3.26 | 3.960 (3) | 132 |
C7—H7B···I2vi | 0.99 | 2.94 | 3.758 (3) | 140 |
Symmetry codes: (ii) −x+1, −y, −z+2; (iii) −x+1, −y+1, −z+2; (iv) −x+1/2, y+1, −z+3/2; (v) x, y+1, z; (vi) −x+1, −y, −z+1. |