The ability of 4-[(benzylamino)carbonyl]-1-methylpyridinium to form iodide salts with cation:iodine ratio different from equimolar was studied and a Hirshfeld surface analysis was performed to investigate the intermolecular interactions.
Supporting information
CCDC references: 2118096; 2118095
Key indicators
Structure: I
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.015 Å
- R factor = 0.053
- wR factor = 0.157
- Data-to-parameter ratio = 21.4
Structure: II
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.025 Å
- Disorder in solvent or counterion
- R factor = 0.065
- wR factor = 0.187
- Data-to-parameter ratio = 17.5
Structure: II
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.025 Å
- Disorder in solvent or counterion
- R factor = 0.065
- wR factor = 0.187
- Data-to-parameter ratio = 17.5
checkCIF/PLATON results
No syntax errors found
Datablock: I
Alert level B
PLAT434_ALERT_2_B Short Inter HL..HL Contact I1 ..I2 3.31 Ang.
x,y,z = 1_555 Check
Alert level C
PLAT234_ALERT_4_C Large Hirshfeld Difference C4 --C7 . 0.18 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C8 --C9 . 0.18 Ang.
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.01542 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A ..I2 . 3.18 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1B ..I2 . 3.11 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8B ..C11 . 2.80 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 6.523 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min). 5 Note
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C14 H15 I2 N2 O1
Atom count from _chemical_formula_moiety:C14 H15 I1 N2 O1
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 1 Report
PLAT012_ALERT_1_G N.O.K. _shelx_res_checksum Found in CIF ...... Please Check
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check
PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters 1 Info
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary . Please Do !
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 2 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ........... 3.1 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
1 ALERT level B = A potentially serious problem, consider carefully
8 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
5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
7 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
Datablock: II
Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections (too) Low .. 39% Check
PLAT234_ALERT_4_B Large Hirshfeld Difference C4B --C5B . 0.28 Ang.
PLAT342_ALERT_3_B Low Bond Precision on C-C Bonds ............... 0.025 Ang.
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.12
Rint given 0.124
PLAT041_ALERT_1_C Calc. and Reported SumFormula Strings Differ Please Check
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... Please Check
PLAT234_ALERT_4_C Large Hirshfeld Difference C4A --C5A . 0.19 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C8A --C9A . 0.23 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C9A --C10A . 0.24 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference N1B --C6B . 0.20 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference N2B --C7B . 0.21 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C2B --C3B . 0.23 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C9B --C14B . 0.21 Ang.
PLAT241_ALERT_2_C High 'MainMol' Ueq as Compared to Neighbors of C8A Check
PLAT241_ALERT_2_C High 'MainMol' Ueq as Compared to Neighbors of C14A Check
PLAT241_ALERT_2_C High 'MainMol' Ueq as Compared to Neighbors of C2B Check
PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of N1A Check
PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of C9A Check
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors of I1 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including I4 0.118 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including I6 0.130 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including I7 0.150 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including I7A 0.150 Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2AA ..I3 . 3.08 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1AA ..I7 . 3.09 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2BA ..C12A . 2.85 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1BB ..I7 . 3.07 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6B ..I4 . 3.12 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 13.062 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 2.105 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min). 10 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.595 8 Report
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C14 H15 I3.01 N2 O1
Atom count from _chemical_formula_moiety:C28 H30 I2 N4 O2
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: check formula stoichiometry or atom site occupancies.
From the CIF: _cell_formula_units_Z 8
From the CIF: _chemical_formula_sum C14 H15 I3.01 N2 O
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 112.00 112.00 0.00
H 120.00 120.00 0.00
I 24.08 24.00 0.08
N 16.00 16.00 0.00
O 8.00 8.00 0.00
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 2 Report
PLAT020_ALERT_3_G The Value of Rint is Greater Than 0.12 ......... 0.124 Report
PLAT042_ALERT_1_G Calc. and Reported Moiety Formula Strings Differ Please Check
PLAT045_ALERT_1_G Calculated and Reported Z Differ by a Factor ... 0.50 Check
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records 1 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check
PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check
PLAT300_ALERT_4_G Atom Site Occupancy of I6 Constrained at 0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of I7 Constrained at 0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of I7A Constrained at 0.5 Check
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd 5 ) 100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd 6 ) 100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd 7 ) 100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd 5 ) 0.50 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd 6 ) 0.50 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd 7 ) 0.50 Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety ..... C1A Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety ..... C1B Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 12 Note
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) . 1.12 Ratio
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle(s) in CIF ... 6.90 Deg.
I7A -I6 -I7 1_555 1_555 1_555 ...... # 5 Check
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle(s) in CIF ... 8.00 Deg.
I6 -I6 -I7A 3_466 1_555 3_466 ...... # 6 Check
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle(s) in CIF ... 14.40 Deg.
I7A -I7 -I6 1_555 1_555 1_555 ...... # 9 Check
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle(s) in CIF ... 3.90 Deg.
I6 -I7A -I6 1_555 1_555 3_466 ...... # 12 Check
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 5 Note
I
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 6 Note
I
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 7 Note
I
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters 1 Info
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary . Please Do !
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ........... 3.2 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
3 ALERT level B = A potentially serious problem, consider carefully
29 ALERT level C = Check. Ensure it is not caused by an omission or oversight
34 ALERT level G = General information/check it is not something unexpected
10 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
10 ALERT type 2 Indicator that the structure model may be wrong or deficient
9 ALERT type 3 Indicator that the structure quality may be low
36 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
For both structures, data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
4-[(Benzylamino)carbonyl]-1-methylpyridinium iodide–iodine (2/1) (I)
top
Crystal data top
C14H15N2O+·I−·0.5I2 | F(000) = 908 |
Mr = 481.08 | Dx = 1.981 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 14.407 (3) Å | Cell parameters from 928 reflections |
b = 8.8491 (10) Å | θ = 3.6–21.8° |
c = 14.555 (4) Å | µ = 3.89 mm−1 |
β = 119.63 (3)° | T = 293 K |
V = 1613.0 (7) Å3 | Stick, red |
Z = 4 | 0.60 × 0.10 × 0.05 mm |
Data collection top
Xcalibur, Sapphire3 diffractometer | 3698 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1941 reflections with I > 2σ(I) |
Detector resolution: 16.1827 pixels mm-1 | Rint = 0.083 |
ω scans | θmax = 27.5°, θmin = 3.2° |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2018) | h = −18→18 |
Tmin = 0.159, Tmax = 1.000 | k = −11→11 |
11491 measured reflections | l = −18→18 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H-atom parameters constrained |
wR(F2) = 0.157 | w = 1/[σ2(Fo2) + (0.0416P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
3698 reflections | Δρmax = 0.90 e Å−3 |
173 parameters | Δρmin = −0.89 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.51630 (5) | 0.11900 (6) | 0.57075 (6) | 0.0696 (2) | |
I2 | 0.55433 (5) | 0.39112 (7) | 0.74152 (6) | 0.0738 (3) | |
O1 | 0.1044 (5) | 0.3003 (8) | 0.5772 (6) | 0.090 (2) | |
N1 | 0.1782 (6) | 0.6060 (7) | 0.3371 (6) | 0.0614 (18) | |
N2 | 0.2820 (6) | 0.2698 (8) | 0.6521 (6) | 0.0652 (19) | |
H2 | 0.338519 | 0.295372 | 0.650010 | 0.078* | |
C1 | 0.1732 (8) | 0.7074 (10) | 0.2544 (8) | 0.075 (3) | |
H1A | 0.127757 | 0.663816 | 0.186085 | 0.113* | |
H1B | 0.243679 | 0.720760 | 0.264125 | 0.113* | |
H1C | 0.145051 | 0.803613 | 0.259012 | 0.113* | |
C2 | 0.2636 (7) | 0.5182 (10) | 0.3929 (8) | 0.069 (3) | |
H2A | 0.320082 | 0.521097 | 0.379074 | 0.083* | |
C3 | 0.2692 (7) | 0.4235 (10) | 0.4707 (8) | 0.067 (2) | |
H3 | 0.327838 | 0.360259 | 0.506976 | 0.081* | |
C4 | 0.1885 (6) | 0.4224 (9) | 0.4944 (8) | 0.062 (2) | |
C5 | 0.1012 (7) | 0.5127 (12) | 0.4336 (8) | 0.078 (3) | |
H5 | 0.043510 | 0.511632 | 0.445534 | 0.093* | |
C6 | 0.0979 (7) | 0.6028 (10) | 0.3569 (8) | 0.070 (3) | |
H6 | 0.038316 | 0.663303 | 0.317556 | 0.084* | |
C7 | 0.1885 (6) | 0.3260 (10) | 0.5791 (7) | 0.057 (2) | |
C8 | 0.2932 (8) | 0.1666 (10) | 0.7357 (8) | 0.073 (3) | |
H8A | 0.362531 | 0.117925 | 0.766315 | 0.087* | |
H8B | 0.239142 | 0.088488 | 0.704706 | 0.087* | |
C9 | 0.2828 (7) | 0.2439 (8) | 0.8213 (7) | 0.057 (2) | |
C10 | 0.3668 (7) | 0.3281 (10) | 0.8984 (8) | 0.068 (2) | |
H10 | 0.431231 | 0.333813 | 0.898376 | 0.082* | |
C11 | 0.3548 (9) | 0.4014 (10) | 0.9732 (9) | 0.081 (3) | |
H11 | 0.410137 | 0.461576 | 1.022065 | 0.097* | |
C12 | 0.2622 (9) | 0.3890 (10) | 0.9788 (9) | 0.078 (3) | |
H12 | 0.255082 | 0.439378 | 1.031040 | 0.094* | |
C13 | 0.1810 (9) | 0.3010 (13) | 0.9058 (9) | 0.083 (3) | |
H13 | 0.118664 | 0.289920 | 0.909431 | 0.099* | |
C14 | 0.1904 (7) | 0.2294 (10) | 0.8280 (9) | 0.071 (3) | |
H14 | 0.134482 | 0.170291 | 0.778882 | 0.085* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.0651 (4) | 0.0655 (4) | 0.0790 (5) | 0.0033 (3) | 0.0364 (4) | −0.0008 (3) |
I2 | 0.0669 (4) | 0.0799 (4) | 0.0809 (5) | −0.0121 (3) | 0.0413 (4) | −0.0181 (3) |
O1 | 0.050 (3) | 0.118 (5) | 0.100 (6) | −0.008 (3) | 0.036 (4) | 0.012 (5) |
N1 | 0.060 (4) | 0.060 (4) | 0.056 (5) | 0.006 (3) | 0.023 (4) | −0.002 (3) |
N2 | 0.058 (4) | 0.068 (4) | 0.074 (6) | −0.007 (3) | 0.036 (4) | 0.003 (4) |
C1 | 0.081 (6) | 0.070 (6) | 0.062 (7) | 0.008 (5) | 0.025 (5) | 0.008 (5) |
C2 | 0.066 (6) | 0.070 (6) | 0.080 (8) | 0.013 (4) | 0.042 (6) | −0.002 (5) |
C3 | 0.057 (5) | 0.083 (6) | 0.073 (7) | 0.018 (4) | 0.040 (5) | 0.006 (5) |
C4 | 0.051 (5) | 0.066 (5) | 0.060 (6) | 0.003 (4) | 0.021 (4) | −0.019 (4) |
C5 | 0.048 (5) | 0.121 (8) | 0.067 (7) | 0.008 (5) | 0.030 (5) | 0.004 (6) |
C6 | 0.059 (5) | 0.075 (6) | 0.073 (7) | 0.017 (4) | 0.031 (5) | 0.005 (5) |
C7 | 0.050 (4) | 0.063 (5) | 0.060 (6) | −0.006 (4) | 0.029 (4) | −0.002 (4) |
C8 | 0.075 (6) | 0.066 (5) | 0.077 (7) | 0.001 (5) | 0.037 (6) | 0.013 (5) |
C9 | 0.067 (5) | 0.048 (4) | 0.060 (6) | 0.005 (4) | 0.035 (5) | 0.006 (4) |
C10 | 0.059 (5) | 0.072 (6) | 0.072 (7) | −0.004 (4) | 0.033 (5) | 0.010 (5) |
C11 | 0.086 (7) | 0.068 (6) | 0.074 (8) | −0.012 (5) | 0.028 (6) | −0.002 (5) |
C12 | 0.092 (8) | 0.072 (6) | 0.073 (8) | 0.027 (5) | 0.043 (7) | 0.017 (5) |
C13 | 0.075 (6) | 0.106 (8) | 0.070 (7) | 0.014 (6) | 0.039 (6) | 0.019 (6) |
C14 | 0.053 (5) | 0.075 (6) | 0.083 (8) | −0.003 (4) | 0.032 (5) | 0.016 (5) |
Geometric parameters (Å, º) top
I1—I1i | 2.8182 (13) | C5—C6 | 1.353 (13) |
O1—C7 | 1.221 (9) | C5—H5 | 0.9300 |
N1—C6 | 1.324 (11) | C6—H6 | 0.9300 |
N1—C2 | 1.338 (10) | C8—C9 | 1.494 (12) |
N1—C1 | 1.475 (11) | C8—H8A | 0.9700 |
N2—C7 | 1.332 (11) | C8—H8B | 0.9700 |
N2—C8 | 1.465 (11) | C9—C14 | 1.387 (11) |
N2—H2 | 0.8600 | C9—C10 | 1.391 (12) |
C1—H1A | 0.9600 | C10—C11 | 1.350 (14) |
C1—H1B | 0.9600 | C10—H10 | 0.9300 |
C1—H1C | 0.9600 | C11—C12 | 1.381 (14) |
C2—C3 | 1.378 (12) | C11—H11 | 0.9300 |
C2—H2A | 0.9300 | C12—C13 | 1.369 (15) |
C3—C4 | 1.366 (11) | C12—H12 | 0.9300 |
C3—H3 | 0.9300 | C13—C14 | 1.362 (14) |
C4—C5 | 1.380 (12) | C13—H13 | 0.9300 |
C4—C7 | 1.499 (13) | C14—H14 | 0.9300 |
| | | |
C6—N1—C2 | 119.8 (8) | O1—C7—N2 | 123.3 (8) |
C6—N1—C1 | 119.7 (7) | O1—C7—C4 | 119.4 (8) |
C2—N1—C1 | 120.5 (8) | N2—C7—C4 | 117.2 (7) |
C7—N2—C8 | 123.3 (7) | N2—C8—C9 | 113.1 (7) |
C7—N2—H2 | 118.4 | N2—C8—H8A | 109.0 |
C8—N2—H2 | 118.4 | C9—C8—H8A | 109.0 |
N1—C1—H1A | 109.5 | N2—C8—H8B | 109.0 |
N1—C1—H1B | 109.5 | C9—C8—H8B | 109.0 |
H1A—C1—H1B | 109.5 | H8A—C8—H8B | 107.8 |
N1—C1—H1C | 109.5 | C14—C9—C10 | 118.4 (9) |
H1A—C1—H1C | 109.5 | C14—C9—C8 | 120.8 (9) |
H1B—C1—H1C | 109.5 | C10—C9—C8 | 120.8 (8) |
N1—C2—C3 | 120.9 (8) | C11—C10—C9 | 120.0 (9) |
N1—C2—H2A | 119.5 | C11—C10—H10 | 120.0 |
C3—C2—H2A | 119.5 | C9—C10—H10 | 120.0 |
C4—C3—C2 | 120.0 (8) | C10—C11—C12 | 121.5 (10) |
C4—C3—H3 | 120.0 | C10—C11—H11 | 119.3 |
C2—C3—H3 | 120.0 | C12—C11—H11 | 119.3 |
C3—C4—C5 | 116.9 (9) | C13—C12—C11 | 118.7 (10) |
C3—C4—C7 | 123.9 (8) | C13—C12—H12 | 120.7 |
C5—C4—C7 | 119.1 (8) | C11—C12—H12 | 120.7 |
C6—C5—C4 | 121.4 (8) | C14—C13—C12 | 120.7 (10) |
C6—C5—H5 | 119.3 | C14—C13—H13 | 119.6 |
C4—C5—H5 | 119.3 | C12—C13—H13 | 119.6 |
N1—C6—C5 | 120.9 (8) | C13—C14—C9 | 120.6 (10) |
N1—C6—H6 | 119.6 | C13—C14—H14 | 119.7 |
C5—C6—H6 | 119.6 | C9—C14—H14 | 119.7 |
| | | |
C6—N1—C2—C3 | 0.4 (14) | C3—C4—C7—N2 | 18.1 (13) |
C1—N1—C2—C3 | 179.7 (9) | C5—C4—C7—N2 | −164.0 (9) |
N1—C2—C3—C4 | −2.5 (14) | C7—N2—C8—C9 | −75.0 (11) |
C2—C3—C4—C5 | 3.5 (13) | N2—C8—C9—C14 | 104.6 (9) |
C2—C3—C4—C7 | −178.6 (9) | N2—C8—C9—C10 | −77.6 (11) |
C3—C4—C5—C6 | −2.7 (14) | C14—C9—C10—C11 | −4.3 (13) |
C7—C4—C5—C6 | 179.3 (9) | C8—C9—C10—C11 | 177.8 (9) |
C2—N1—C6—C5 | 0.5 (14) | C9—C10—C11—C12 | 3.4 (15) |
C1—N1—C6—C5 | −178.9 (9) | C10—C11—C12—C13 | −0.5 (15) |
C4—C5—C6—N1 | 0.7 (16) | C11—C12—C13—C14 | −1.3 (15) |
C8—N2—C7—O1 | 2.3 (14) | C12—C13—C14—C9 | 0.2 (15) |
C8—N2—C7—C4 | −176.2 (8) | C10—C9—C14—C13 | 2.6 (13) |
C3—C4—C7—O1 | −160.5 (9) | C8—C9—C14—C13 | −179.5 (9) |
C5—C4—C7—O1 | 17.4 (13) | | |
Symmetry code: (i) −x+1, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···I2 | 0.86 | 2.84 | 3.632 (7) | 154 |
C2—H2A···I2ii | 0.93 | 3.18 | 4.053 (9) | 158 |
C1—H1B···I2ii | 0.96 | 3.11 | 3.992 (9) | 153 |
C1—H1C···I2iii | 0.96 | 2.96 | 3.908 (9) | 171 |
C1—H1A···I1iv | 0.96 | 3.00 | 3.824 (10) | 145 |
C5—H5···O1v | 0.93 | 2.59 | 3.328 (11) | 136 |
C8—H8B···C11vi | 0.97 | 2.80 | 3.590 (15) | 140 |
C8—H8B···C10vi | 0.97 | 2.76 | 3.694 (14) | 162 |
Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) x−1/2, −y+3/2, z−1/2; (iv) x−1/2, −y+1/2, z−1/2; (v) −x, −y+1, −z+1; (vi) −x+1/2, y−1/2, −z+3/2. |
4-[(Benzylamino)carbonyl]-1-methylpyridinium triiodide (II)
top
Crystal data top
C14H15N2O+·I3− | F(000) = 2242 |
Mr = 608.61 | Dx = 2.183 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.914 (2) Å | Cell parameters from 1078 reflections |
b = 27.805 (4) Å | θ = 3.1–18.1° |
c = 14.113 (3) Å | µ = 5.07 mm−1 |
β = 107.83 (2)° | T = 293 K |
V = 3703.4 (12) Å3 | Block, yellow |
Z = 8 | 0.03 × 0.03 × 0.02 mm |
Data collection top
Xcalibur, Sapphire3 diffractometer | 6496 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2548 reflections with I > 2σ(I) |
Detector resolution: 16.1827 pixels mm-1 | Rint = 0.124 |
ω scans | θmax = 25.0°, θmin = 3.0° |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2018) | h = −8→11 |
Tmin = 0.347, Tmax = 1.000 | k = −33→33 |
21040 measured reflections | l = −16→16 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.065 | H-atom parameters constrained |
wR(F2) = 0.187 | w = 1/[σ2(Fo2) + (0.0424P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max < 0.001 |
6496 reflections | Δρmax = 0.70 e Å−3 |
371 parameters | Δρmin = −0.77 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
I1 | 0.45921 (12) | 0.79328 (4) | 0.65364 (9) | 0.0868 (4) | |
I2 | 0.46503 (14) | 0.71598 (5) | 0.78702 (11) | 0.1072 (4) | |
I3 | 0.45434 (15) | 0.87375 (4) | 0.50883 (10) | 0.1061 (5) | |
I4 | 0.000000 | 1.000000 | 0.500000 | 0.1048 (6) | |
I5 | −0.09620 (18) | 0.93095 (5) | 0.62111 (13) | 0.1313 (6) | |
I6 | −0.4785 (8) | 0.5112 (2) | 0.5262 (5) | 0.130 (2) | 0.5 |
I7 | −0.3252 (7) | 0.5746 (2) | 0.6849 (5) | 0.1504 (17) | 0.5 |
I7A | −0.3531 (7) | 0.5527 (2) | 0.6302 (5) | 0.1504 (17) | 0.5 |
O1A | −0.1281 (11) | 0.6399 (4) | 0.3910 (8) | 0.092 (3) | |
N1A | 0.0042 (18) | 0.8083 (4) | 0.3781 (10) | 0.081 (4) | |
N2A | 0.0997 (12) | 0.6306 (4) | 0.4111 (9) | 0.078 (4) | |
H2A | 0.175586 | 0.643198 | 0.404694 | 0.094* | |
C1A | 0.004 (2) | 0.8621 (5) | 0.3785 (13) | 0.110 (6) | |
H1AA | −0.091508 | 0.873532 | 0.349446 | 0.165* | |
H1AB | 0.039744 | 0.873527 | 0.445762 | 0.165* | |
H1AC | 0.062284 | 0.873811 | 0.340557 | 0.165* | |
C2A | 0.1245 (19) | 0.7843 (6) | 0.4148 (13) | 0.096 (5) | |
H2AA | 0.209343 | 0.801051 | 0.438759 | 0.115* | |
C3A | 0.1251 (16) | 0.7345 (6) | 0.4178 (12) | 0.088 (5) | |
H3A | 0.210205 | 0.717786 | 0.440984 | 0.106* | |
C4A | 0.0012 (16) | 0.7105 (6) | 0.3867 (12) | 0.079 (4) | |
C5A | −0.1202 (19) | 0.7349 (6) | 0.3482 (12) | 0.089 (5) | |
H5A | −0.205655 | 0.718459 | 0.324995 | 0.107* | |
C6A | −0.1183 (19) | 0.7837 (7) | 0.3431 (13) | 0.095 (5) | |
H6A | −0.202505 | 0.800379 | 0.315060 | 0.114* | |
C7A | −0.0134 (16) | 0.6579 (6) | 0.3940 (11) | 0.079 (4) | |
C8A | 0.1044 (17) | 0.5796 (5) | 0.4403 (13) | 0.092 (5) | |
H8AA | 0.181584 | 0.564057 | 0.423495 | 0.110* | |
H8AB | 0.016959 | 0.564255 | 0.401688 | 0.110* | |
C9A | 0.1238 (18) | 0.5715 (5) | 0.5504 (12) | 0.074 (4) | |
C10A | 0.252 (2) | 0.5902 (6) | 0.6130 (16) | 0.097 (6) | |
H10A | 0.316106 | 0.605499 | 0.587126 | 0.117* | |
C11A | 0.279 (2) | 0.5848 (6) | 0.7157 (17) | 0.106 (6) | |
H11A | 0.360108 | 0.597669 | 0.760162 | 0.128* | |
C12A | 0.184 (2) | 0.5606 (7) | 0.7493 (16) | 0.106 (6) | |
H12A | 0.203600 | 0.554933 | 0.817130 | 0.127* | |
C13A | 0.060 (2) | 0.5444 (6) | 0.685 (2) | 0.107 (7) | |
H13A | −0.005324 | 0.529527 | 0.710907 | 0.128* | |
C14A | 0.027 (2) | 0.5491 (7) | 0.5838 (17) | 0.121 (7) | |
H14A | −0.057924 | 0.537576 | 0.540700 | 0.145* | |
O1B | 0.3841 (10) | 0.6543 (4) | 0.4242 (8) | 0.086 (3) | |
N1B | 0.4543 (16) | 0.5322 (5) | 0.1922 (12) | 0.088 (4) | |
N2B | 0.6125 (12) | 0.6628 (4) | 0.4475 (8) | 0.076 (4) | |
H2B | 0.684595 | 0.655003 | 0.429131 | 0.091* | |
C1B | 0.4388 (19) | 0.4928 (6) | 0.1164 (14) | 0.108 (6) | |
H1BA | 0.530747 | 0.480708 | 0.119642 | 0.162* | |
H1BB | 0.382401 | 0.467282 | 0.130134 | 0.162* | |
H1BC | 0.393375 | 0.505462 | 0.051088 | 0.162* | |
C2B | 0.581 (2) | 0.5433 (6) | 0.2527 (16) | 0.102 (6) | |
H2BA | 0.658994 | 0.525293 | 0.250589 | 0.123* | |
C3B | 0.5997 (15) | 0.5805 (5) | 0.3180 (12) | 0.074 (4) | |
H3B | 0.690985 | 0.589253 | 0.355599 | 0.088* | |
C4B | 0.4836 (14) | 0.6059 (5) | 0.3296 (11) | 0.069 (4) | |
C5B | 0.356 (2) | 0.5904 (6) | 0.2686 (12) | 0.089 (5) | |
H5B | 0.273994 | 0.605203 | 0.272963 | 0.107* | |
C6B | 0.3436 (18) | 0.5548 (6) | 0.2030 (12) | 0.090 (5) | |
H6B | 0.253572 | 0.545749 | 0.163528 | 0.107* | |
C7B | 0.4904 (17) | 0.6428 (5) | 0.4034 (11) | 0.071 (4) | |
C8B | 0.6312 (18) | 0.6988 (5) | 0.5285 (12) | 0.085 (5) | |
H8BA | 0.569928 | 0.726128 | 0.502782 | 0.102* | |
H8BB | 0.601106 | 0.684595 | 0.581491 | 0.102* | |
C9B | 0.7765 (16) | 0.7161 (6) | 0.5702 (11) | 0.072 (4) | |
C10B | 0.8890 (17) | 0.6853 (6) | 0.6049 (12) | 0.084 (4) | |
H10B | 0.872179 | 0.652312 | 0.601274 | 0.100* | |
C11B | 1.024 (2) | 0.7013 (7) | 0.6443 (13) | 0.097 (5) | |
H11B | 1.097443 | 0.679375 | 0.668821 | 0.116* | |
C12B | 1.0525 (19) | 0.7495 (8) | 0.6480 (11) | 0.094 (5) | |
H12B | 1.144660 | 0.760430 | 0.676679 | 0.112* | |
C13B | 0.946 (2) | 0.7812 (7) | 0.6098 (13) | 0.096 (5) | |
H13B | 0.966127 | 0.813824 | 0.608168 | 0.115* | |
C14B | 0.8040 (16) | 0.7646 (6) | 0.5720 (11) | 0.081 (5) | |
H14B | 0.730116 | 0.786363 | 0.548735 | 0.097* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.0752 (7) | 0.0882 (8) | 0.0963 (8) | −0.0041 (6) | 0.0254 (6) | −0.0169 (6) |
I2 | 0.0868 (9) | 0.0985 (9) | 0.1316 (11) | −0.0025 (7) | 0.0264 (8) | 0.0075 (8) |
I3 | 0.1210 (11) | 0.0961 (9) | 0.0995 (9) | −0.0168 (8) | 0.0312 (8) | −0.0034 (7) |
I4 | 0.0852 (12) | 0.0960 (13) | 0.1177 (14) | 0.0118 (10) | 0.0082 (10) | −0.0004 (10) |
I5 | 0.1384 (14) | 0.1108 (11) | 0.1504 (14) | 0.0019 (10) | 0.0526 (12) | 0.0023 (9) |
I6 | 0.099 (4) | 0.131 (5) | 0.180 (7) | 0.027 (3) | 0.072 (5) | 0.077 (4) |
I7 | 0.117 (3) | 0.148 (4) | 0.200 (6) | −0.001 (3) | 0.069 (4) | 0.048 (3) |
I7A | 0.117 (3) | 0.148 (4) | 0.200 (6) | −0.001 (3) | 0.069 (4) | 0.048 (3) |
O1A | 0.068 (7) | 0.091 (8) | 0.123 (10) | −0.009 (6) | 0.039 (7) | −0.023 (6) |
N1A | 0.106 (11) | 0.062 (8) | 0.085 (9) | 0.004 (8) | 0.043 (9) | 0.012 (7) |
N2A | 0.048 (7) | 0.080 (9) | 0.105 (10) | −0.015 (7) | 0.022 (7) | −0.018 (7) |
C1A | 0.137 (18) | 0.073 (11) | 0.116 (15) | −0.004 (11) | 0.031 (13) | 0.013 (10) |
C2A | 0.071 (12) | 0.091 (13) | 0.124 (15) | −0.013 (10) | 0.029 (11) | 0.002 (11) |
C3A | 0.058 (10) | 0.079 (11) | 0.115 (14) | −0.002 (9) | 0.008 (9) | 0.013 (9) |
C4A | 0.048 (9) | 0.093 (12) | 0.086 (11) | −0.011 (9) | 0.005 (8) | −0.001 (9) |
C5A | 0.085 (13) | 0.089 (13) | 0.087 (12) | −0.024 (11) | 0.018 (10) | −0.002 (9) |
C6A | 0.069 (11) | 0.121 (16) | 0.098 (13) | 0.017 (12) | 0.031 (10) | 0.017 (11) |
C7A | 0.050 (9) | 0.110 (14) | 0.076 (11) | −0.004 (10) | 0.021 (8) | −0.010 (9) |
C8A | 0.078 (12) | 0.075 (11) | 0.125 (16) | −0.011 (9) | 0.035 (11) | −0.017 (10) |
C9A | 0.080 (11) | 0.064 (10) | 0.067 (11) | −0.006 (8) | 0.009 (9) | −0.018 (8) |
C10A | 0.108 (15) | 0.081 (12) | 0.122 (16) | −0.001 (11) | 0.063 (14) | −0.017 (11) |
C11A | 0.087 (14) | 0.105 (15) | 0.125 (18) | −0.001 (11) | 0.029 (13) | −0.021 (12) |
C12A | 0.094 (15) | 0.113 (16) | 0.112 (16) | 0.024 (13) | 0.034 (14) | 0.002 (12) |
C13A | 0.114 (17) | 0.074 (12) | 0.16 (2) | 0.003 (12) | 0.084 (17) | 0.024 (13) |
C14A | 0.125 (18) | 0.140 (18) | 0.120 (19) | −0.011 (15) | 0.072 (16) | −0.011 (14) |
O1B | 0.058 (7) | 0.107 (8) | 0.098 (8) | −0.007 (6) | 0.029 (6) | −0.016 (6) |
N1B | 0.087 (10) | 0.073 (9) | 0.120 (12) | 0.009 (8) | 0.058 (10) | −0.002 (8) |
N2B | 0.042 (7) | 0.105 (10) | 0.078 (9) | −0.011 (7) | 0.014 (6) | −0.018 (7) |
C1B | 0.105 (15) | 0.101 (13) | 0.120 (15) | −0.017 (11) | 0.036 (13) | −0.017 (12) |
C2B | 0.075 (13) | 0.060 (11) | 0.18 (2) | −0.006 (10) | 0.048 (14) | 0.007 (12) |
C3B | 0.056 (9) | 0.054 (9) | 0.109 (13) | −0.012 (7) | 0.021 (9) | −0.012 (8) |
C4B | 0.043 (8) | 0.073 (10) | 0.086 (11) | −0.010 (7) | 0.011 (7) | −0.005 (8) |
C5B | 0.113 (15) | 0.084 (12) | 0.085 (12) | 0.011 (11) | 0.054 (12) | −0.009 (9) |
C6B | 0.072 (11) | 0.116 (15) | 0.081 (12) | −0.019 (11) | 0.023 (10) | −0.007 (10) |
C7B | 0.073 (10) | 0.075 (10) | 0.077 (11) | 0.015 (9) | 0.038 (9) | 0.005 (8) |
C8B | 0.094 (13) | 0.075 (10) | 0.086 (11) | −0.011 (9) | 0.028 (10) | −0.014 (9) |
C9B | 0.068 (10) | 0.077 (11) | 0.075 (10) | −0.012 (9) | 0.030 (8) | −0.018 (8) |
C10B | 0.066 (11) | 0.089 (12) | 0.089 (12) | 0.011 (10) | 0.014 (9) | 0.003 (9) |
C11B | 0.077 (13) | 0.125 (16) | 0.092 (13) | 0.005 (12) | 0.030 (11) | 0.003 (11) |
C12B | 0.072 (12) | 0.140 (17) | 0.064 (11) | −0.021 (13) | 0.014 (9) | −0.016 (11) |
C13B | 0.090 (13) | 0.104 (13) | 0.097 (13) | −0.006 (12) | 0.034 (11) | 0.002 (11) |
C14B | 0.052 (9) | 0.112 (14) | 0.069 (10) | 0.014 (9) | 0.005 (8) | −0.014 (9) |
Geometric parameters (Å, º) top
I1—I2 | 2.8459 (18) | C12A—H12A | 0.9300 |
I1—I3 | 3.0206 (17) | C13A—C14A | 1.37 (3) |
I4—I5 | 2.9181 (15) | C13A—H13A | 0.9300 |
I4—I5i | 2.9181 (15) | C14A—H14A | 0.9300 |
I6—I6ii | 0.962 (9) | O1B—C7B | 1.220 (15) |
I6—I7A | 1.977 (7) | N1B—C6B | 1.313 (18) |
I6—I7 | 2.890 (7) | N1B—C2B | 1.32 (2) |
I6—I7Aii | 2.925 (7) | N1B—C1B | 1.504 (19) |
I7—I7A | 0.957 (7) | N2B—C7B | 1.305 (17) |
O1A—C7A | 1.231 (16) | N2B—C8B | 1.488 (17) |
N1A—C2A | 1.327 (19) | N2B—H2B | 0.8600 |
N1A—C6A | 1.35 (2) | C1B—H1BA | 0.9600 |
N1A—C1A | 1.495 (17) | C1B—H1BB | 0.9600 |
N2A—C7A | 1.315 (17) | C1B—H1BC | 0.9600 |
N2A—C8A | 1.472 (17) | C2B—C3B | 1.36 (2) |
N2A—H2A | 0.8600 | C2B—H2BA | 0.9300 |
C1A—H1AA | 0.9600 | C3B—C4B | 1.403 (18) |
C1A—H1AB | 0.9600 | C3B—H3B | 0.9300 |
C1A—H1AC | 0.9600 | C4B—C5B | 1.36 (2) |
C2A—C3A | 1.39 (2) | C4B—C7B | 1.447 (19) |
C2A—H2AA | 0.9300 | C5B—C6B | 1.335 (19) |
C3A—C4A | 1.348 (19) | C5B—H5B | 0.9300 |
C3A—H3A | 0.9300 | C6B—H6B | 0.9300 |
C4A—C5A | 1.34 (2) | C8B—C9B | 1.46 (2) |
C4A—C7A | 1.48 (2) | C8B—H8BA | 0.9700 |
C5A—C6A | 1.36 (2) | C8B—H8BB | 0.9700 |
C5A—H5A | 0.9300 | C9B—C10B | 1.372 (19) |
C6A—H6A | 0.9300 | C9B—C14B | 1.374 (19) |
C8A—C9A | 1.52 (2) | C10B—C11B | 1.36 (2) |
C8A—H8AA | 0.9700 | C10B—H10B | 0.9300 |
C8A—H8AB | 0.9700 | C11B—C12B | 1.37 (2) |
C9A—C14A | 1.35 (2) | C11B—H11B | 0.9300 |
C9A—C10A | 1.40 (2) | C12B—C13B | 1.35 (2) |
C10A—C11A | 1.40 (2) | C12B—H12B | 0.9300 |
C10A—H10A | 0.9300 | C13B—C14B | 1.42 (2) |
C11A—C12A | 1.35 (2) | C13B—H13B | 0.9300 |
C11A—H11A | 0.9300 | C14B—H14B | 0.9300 |
C12A—C13A | 1.36 (3) | | |
| | | |
I2—I1—I3 | 178.72 (5) | C12A—C13A—C14A | 122.8 (18) |
I5—I4—I5i | 180.0 | C12A—C13A—H13A | 118.6 |
I6ii—I6—I7A | 168.1 (11) | C14A—C13A—H13A | 118.6 |
I6ii—I6—I7 | 174.9 (11) | C9A—C14A—C13A | 116 (2) |
I7A—I6—I7 | 6.9 (3) | C9A—C14A—H14A | 121.9 |
I6ii—I6—I7Aii | 8.0 (8) | C13A—C14A—H14A | 121.9 |
I7A—I6—I7Aii | 176.1 (4) | C6B—N1B—C2B | 118.4 (15) |
I7—I6—I7Aii | 176.9 (4) | C6B—N1B—C1B | 121.6 (16) |
I7A—I7—I6 | 14.4 (7) | C2B—N1B—C1B | 120.0 (15) |
I7—I7A—I6 | 158.7 (10) | C7B—N2B—C8B | 122.2 (12) |
I7—I7A—I6ii | 162.5 (9) | C7B—N2B—H2B | 118.9 |
I6—I7A—I6ii | 3.9 (4) | C8B—N2B—H2B | 118.9 |
C2A—N1A—C6A | 119.2 (14) | N1B—C1B—H1BA | 109.5 |
C2A—N1A—C1A | 120.4 (16) | N1B—C1B—H1BB | 109.5 |
C6A—N1A—C1A | 120.3 (16) | H1BA—C1B—H1BB | 109.5 |
C7A—N2A—C8A | 124.0 (13) | N1B—C1B—H1BC | 109.5 |
C7A—N2A—H2A | 118.0 | H1BA—C1B—H1BC | 109.5 |
C8A—N2A—H2A | 118.0 | H1BB—C1B—H1BC | 109.5 |
N1A—C1A—H1AA | 109.5 | N1B—C2B—C3B | 121.5 (16) |
N1A—C1A—H1AB | 109.5 | N1B—C2B—H2BA | 119.3 |
H1AA—C1A—H1AB | 109.5 | C3B—C2B—H2BA | 119.3 |
N1A—C1A—H1AC | 109.5 | C2B—C3B—C4B | 121.0 (15) |
H1AA—C1A—H1AC | 109.5 | C2B—C3B—H3B | 119.5 |
H1AB—C1A—H1AC | 109.5 | C4B—C3B—H3B | 119.5 |
N1A—C2A—C3A | 120.7 (16) | C5B—C4B—C3B | 113.7 (14) |
N1A—C2A—H2AA | 119.6 | C5B—C4B—C7B | 120.6 (14) |
C3A—C2A—H2AA | 119.6 | C3B—C4B—C7B | 125.5 (14) |
C4A—C3A—C2A | 119.3 (16) | C6B—C5B—C4B | 122.9 (16) |
C4A—C3A—H3A | 120.3 | C6B—C5B—H5B | 118.5 |
C2A—C3A—H3A | 120.3 | C4B—C5B—H5B | 118.5 |
C5A—C4A—C3A | 119.7 (16) | N1B—C6B—C5B | 122.2 (17) |
C5A—C4A—C7A | 115.8 (14) | N1B—C6B—H6B | 118.9 |
C3A—C4A—C7A | 124.5 (15) | C5B—C6B—H6B | 118.9 |
C4A—C5A—C6A | 120.1 (17) | O1B—C7B—N2B | 121.1 (14) |
C4A—C5A—H5A | 120.0 | O1B—C7B—C4B | 120.4 (15) |
C6A—C5A—H5A | 120.0 | N2B—C7B—C4B | 118.6 (13) |
N1A—C6A—C5A | 120.8 (17) | C9B—C8B—N2B | 113.9 (13) |
N1A—C6A—H6A | 119.6 | C9B—C8B—H8BA | 108.8 |
C5A—C6A—H6A | 119.6 | N2B—C8B—H8BA | 108.8 |
O1A—C7A—N2A | 119.8 (16) | C9B—C8B—H8BB | 108.8 |
O1A—C7A—C4A | 120.7 (14) | N2B—C8B—H8BB | 108.8 |
N2A—C7A—C4A | 119.3 (14) | H8BA—C8B—H8BB | 107.7 |
N2A—C8A—C9A | 114.4 (12) | C10B—C9B—C14B | 118.1 (15) |
N2A—C8A—H8AA | 108.7 | C10B—C9B—C8B | 122.2 (15) |
C9A—C8A—H8AA | 108.7 | C14B—C9B—C8B | 119.6 (15) |
N2A—C8A—H8AB | 108.7 | C11B—C10B—C9B | 122.2 (17) |
C9A—C8A—H8AB | 108.7 | C11B—C10B—H10B | 118.9 |
H8AA—C8A—H8AB | 107.6 | C9B—C10B—H10B | 118.9 |
C14A—C9A—C10A | 123.7 (18) | C10B—C11B—C12B | 120.2 (18) |
C14A—C9A—C8A | 123.0 (17) | C10B—C11B—H11B | 119.9 |
C10A—C9A—C8A | 113.2 (16) | C12B—C11B—H11B | 119.9 |
C11A—C10A—C9A | 117.4 (17) | C13B—C12B—C11B | 119.9 (18) |
C11A—C10A—H10A | 121.3 | C13B—C12B—H12B | 120.1 |
C9A—C10A—H10A | 121.3 | C11B—C12B—H12B | 120.1 |
C12A—C11A—C10A | 119 (2) | C12B—C13B—C14B | 119.9 (17) |
C12A—C11A—H11A | 120.5 | C12B—C13B—H13B | 120.1 |
C10A—C11A—H11A | 120.5 | C14B—C13B—H13B | 120.1 |
C11A—C12A—C13A | 121 (2) | C9B—C14B—C13B | 119.6 (16) |
C11A—C12A—H12A | 119.6 | C9B—C14B—H14B | 120.2 |
C13A—C12A—H12A | 119.6 | C13B—C14B—H14B | 120.2 |
| | | |
I6—I7—I7A—I6ii | −2.0 (11) | C6B—N1B—C2B—C3B | −7 (3) |
C6A—N1A—C2A—C3A | 0 (2) | C1B—N1B—C2B—C3B | 176.0 (14) |
C1A—N1A—C2A—C3A | 177.8 (15) | N1B—C2B—C3B—C4B | 6 (3) |
N1A—C2A—C3A—C4A | −3 (3) | C2B—C3B—C4B—C5B | −2 (2) |
C2A—C3A—C4A—C5A | 4 (3) | C2B—C3B—C4B—C7B | 173.6 (15) |
C2A—C3A—C4A—C7A | −174.6 (15) | C3B—C4B—C5B—C6B | −1 (2) |
C3A—C4A—C5A—C6A | −2 (3) | C7B—C4B—C5B—C6B | −176.4 (14) |
C7A—C4A—C5A—C6A | 176.7 (14) | C2B—N1B—C6B—C5B | 4 (3) |
C2A—N1A—C6A—C5A | 2 (2) | C1B—N1B—C6B—C5B | −178.7 (15) |
C1A—N1A—C6A—C5A | −175.8 (14) | C4B—C5B—C6B—N1B | 0 (3) |
C4A—C5A—C6A—N1A | −1 (2) | C8B—N2B—C7B—O1B | 3 (2) |
C8A—N2A—C7A—O1A | −8 (2) | C8B—N2B—C7B—C4B | −176.2 (13) |
C8A—N2A—C7A—C4A | 166.8 (14) | C5B—C4B—C7B—O1B | 13 (2) |
C5A—C4A—C7A—O1A | −19 (2) | C3B—C4B—C7B—O1B | −161.8 (15) |
C3A—C4A—C7A—O1A | 159.5 (17) | C5B—C4B—C7B—N2B | −167.7 (14) |
C5A—C4A—C7A—N2A | 166.0 (15) | C3B—C4B—C7B—N2B | 18 (2) |
C3A—C4A—C7A—N2A | −16 (2) | C7B—N2B—C8B—C9B | 178.3 (14) |
C7A—N2A—C8A—C9A | −81 (2) | N2B—C8B—C9B—C10B | −53 (2) |
N2A—C8A—C9A—C14A | 117.5 (17) | N2B—C8B—C9B—C14B | 124.6 (15) |
N2A—C8A—C9A—C10A | −61.6 (18) | C14B—C9B—C10B—C11B | 3 (2) |
C14A—C9A—C10A—C11A | 0 (3) | C8B—C9B—C10B—C11B | −179.5 (15) |
C8A—C9A—C10A—C11A | 179.4 (14) | C9B—C10B—C11B—C12B | −2 (3) |
C9A—C10A—C11A—C12A | 2 (3) | C10B—C11B—C12B—C13B | −2 (3) |
C10A—C11A—C12A—C13A | −4 (3) | C11B—C12B—C13B—C14B | 4 (2) |
C11A—C12A—C13A—C14A | 4 (3) | C10B—C9B—C14B—C13B | 0 (2) |
C10A—C9A—C14A—C13A | −1 (3) | C8B—C9B—C14B—C13B | −178.0 (14) |
C8A—C9A—C14A—C13A | 179.8 (15) | C12B—C13B—C14B—C9B | −3 (2) |
C12A—C13A—C14A—C9A | −1 (3) | | |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x−1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2A···O1B | 0.86 | 2.02 | 2.846 (14) | 160 |
C3A—H3A···O1B | 0.93 | 2.53 | 3.381 (18) | 152 |
C2A—H2AA···I3 | 0.93 | 3.08 | 3.998 (17) | 169 |
C1A—H1AC···C12Aiii | 0.96 | 2.72 | 3.62 (2) | 158 |
C1A—H1AA···I7iii | 0.96 | 3.09 | 3.966 (19) | 153 |
N2B—H2B···O1Aiv | 0.86 | 2.13 | 2.986 (14) | 176 |
C3B—H3B···O1Aiv | 0.93 | 2.21 | 3.060 (17) | 151 |
C2B—H2BA···C12Av | 0.93 | 2.85 | 3.72 (2) | 156 |
C1B—H1BB···I7vi | 0.96 | 3.07 | 3.819 (18) | 136 |
C6B—H6B···I4vii | 0.93 | 3.12 | 4.019 (17) | 164 |
Symmetry codes: (iii) x, −y+3/2, z−1/2; (iv) x+1, y, z; (v) −x+1, −y+1, −z+1; (vi) −x, −y+1, −z+1; (vii) −x, y−1/2, −z+1/2. |
Selected geometrical parameters (Å, °) for the cations in salts I and
II topParameter | I | IIA | IIB |
N1—C2 | 1.338 (10) | 1.327 (19) | 1.32 (2) |
N1—C6 | 1.324 (11) | 1.35 (2) | 1.313 (18) |
N2—C7—C4—C3 | 18.1 (13) | -16 (2) | 18 (2) |
C7—N2—C8—C9 | -75.0 (11) | -81 (2) | 178.3 (14) |
N2—C8—C9—C10 | -77.6 (11) | -61.6 (18) | -53 (2) |
H2···H3 | 2.09 | 2.14 | 2.11 |
C3···H2 | 2.55 | 2.61 | 2.57 |