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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989021011300/ex2050sup1.cif
Contains datablocks I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989021011300/ex2050Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989021011300/ex2050IIsup3.hkl
Contains datablock II

CCDC references: 2118096; 2118095

Key indicators

Structure: I
  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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 [sigma](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 [sigma](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

Computing details top

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·0.5I2F(000) = 908
Mr = 481.08Dx = 1.981 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 14.407 (3) ÅCell parameters from 928 reflections
b = 8.8491 (10) Åθ = 3.6–21.8°
c = 14.555 (4) ŵ = 3.89 mm1
β = 119.63 (3)°T = 293 K
V = 1613.0 (7) Å3Stick, red
Z = 40.60 × 0.10 × 0.05 mm
Data collection top
Xcalibur, Sapphire3
diffractometer
3698 independent reflections
Radiation source: Enhance (Mo) X-ray Source1941 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm-1Rint = 0.083
ω scansθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2018)
h = 1818
Tmin = 0.159, Tmax = 1.000k = 1111
11491 measured reflectionsl = 1818
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H-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 reflectionsΔρmax = 0.90 e Å3
173 parametersΔρmin = 0.89 e Å3
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
xyzUiso*/Ueq
I10.51630 (5)0.11900 (6)0.57075 (6)0.0696 (2)
I20.55433 (5)0.39112 (7)0.74152 (6)0.0738 (3)
O10.1044 (5)0.3003 (8)0.5772 (6)0.090 (2)
N10.1782 (6)0.6060 (7)0.3371 (6)0.0614 (18)
N20.2820 (6)0.2698 (8)0.6521 (6)0.0652 (19)
H20.3385190.2953720.6500100.078*
C10.1732 (8)0.7074 (10)0.2544 (8)0.075 (3)
H1A0.1277570.6638160.1860850.113*
H1B0.2436790.7207600.2641250.113*
H1C0.1450510.8036130.2590120.113*
C20.2636 (7)0.5182 (10)0.3929 (8)0.069 (3)
H2A0.3200820.5210970.3790740.083*
C30.2692 (7)0.4235 (10)0.4707 (8)0.067 (2)
H30.3278380.3602590.5069760.081*
C40.1885 (6)0.4224 (9)0.4944 (8)0.062 (2)
C50.1012 (7)0.5127 (12)0.4336 (8)0.078 (3)
H50.0435100.5116320.4455340.093*
C60.0979 (7)0.6028 (10)0.3569 (8)0.070 (3)
H60.0383160.6633030.3175560.084*
C70.1885 (6)0.3260 (10)0.5791 (7)0.057 (2)
C80.2932 (8)0.1666 (10)0.7357 (8)0.073 (3)
H8A0.3625310.1179250.7663150.087*
H8B0.2391420.0884880.7047060.087*
C90.2828 (7)0.2439 (8)0.8213 (7)0.057 (2)
C100.3668 (7)0.3281 (10)0.8984 (8)0.068 (2)
H100.4312310.3338130.8983760.082*
C110.3548 (9)0.4014 (10)0.9732 (9)0.081 (3)
H110.4101370.4615761.0220650.097*
C120.2622 (9)0.3890 (10)0.9788 (9)0.078 (3)
H120.2550820.4393781.0310400.094*
C130.1810 (9)0.3010 (13)0.9058 (9)0.083 (3)
H130.1186640.2899200.9094310.099*
C140.1904 (7)0.2294 (10)0.8280 (9)0.071 (3)
H140.1344820.1702910.7788820.085*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0651 (4)0.0655 (4)0.0790 (5)0.0033 (3)0.0364 (4)0.0008 (3)
I20.0669 (4)0.0799 (4)0.0809 (5)0.0121 (3)0.0413 (4)0.0181 (3)
O10.050 (3)0.118 (5)0.100 (6)0.008 (3)0.036 (4)0.012 (5)
N10.060 (4)0.060 (4)0.056 (5)0.006 (3)0.023 (4)0.002 (3)
N20.058 (4)0.068 (4)0.074 (6)0.007 (3)0.036 (4)0.003 (4)
C10.081 (6)0.070 (6)0.062 (7)0.008 (5)0.025 (5)0.008 (5)
C20.066 (6)0.070 (6)0.080 (8)0.013 (4)0.042 (6)0.002 (5)
C30.057 (5)0.083 (6)0.073 (7)0.018 (4)0.040 (5)0.006 (5)
C40.051 (5)0.066 (5)0.060 (6)0.003 (4)0.021 (4)0.019 (4)
C50.048 (5)0.121 (8)0.067 (7)0.008 (5)0.030 (5)0.004 (6)
C60.059 (5)0.075 (6)0.073 (7)0.017 (4)0.031 (5)0.005 (5)
C70.050 (4)0.063 (5)0.060 (6)0.006 (4)0.029 (4)0.002 (4)
C80.075 (6)0.066 (5)0.077 (7)0.001 (5)0.037 (6)0.013 (5)
C90.067 (5)0.048 (4)0.060 (6)0.005 (4)0.035 (5)0.006 (4)
C100.059 (5)0.072 (6)0.072 (7)0.004 (4)0.033 (5)0.010 (5)
C110.086 (7)0.068 (6)0.074 (8)0.012 (5)0.028 (6)0.002 (5)
C120.092 (8)0.072 (6)0.073 (8)0.027 (5)0.043 (7)0.017 (5)
C130.075 (6)0.106 (8)0.070 (7)0.014 (6)0.039 (6)0.019 (6)
C140.053 (5)0.075 (6)0.083 (8)0.003 (4)0.032 (5)0.016 (5)
Geometric parameters (Å, º) top
I1—I1i2.8182 (13)C5—C61.353 (13)
O1—C71.221 (9)C5—H50.9300
N1—C61.324 (11)C6—H60.9300
N1—C21.338 (10)C8—C91.494 (12)
N1—C11.475 (11)C8—H8A0.9700
N2—C71.332 (11)C8—H8B0.9700
N2—C81.465 (11)C9—C141.387 (11)
N2—H20.8600C9—C101.391 (12)
C1—H1A0.9600C10—C111.350 (14)
C1—H1B0.9600C10—H100.9300
C1—H1C0.9600C11—C121.381 (14)
C2—C31.378 (12)C11—H110.9300
C2—H2A0.9300C12—C131.369 (15)
C3—C41.366 (11)C12—H120.9300
C3—H30.9300C13—C141.362 (14)
C4—C51.380 (12)C13—H130.9300
C4—C71.499 (13)C14—H140.9300
C6—N1—C2119.8 (8)O1—C7—N2123.3 (8)
C6—N1—C1119.7 (7)O1—C7—C4119.4 (8)
C2—N1—C1120.5 (8)N2—C7—C4117.2 (7)
C7—N2—C8123.3 (7)N2—C8—C9113.1 (7)
C7—N2—H2118.4N2—C8—H8A109.0
C8—N2—H2118.4C9—C8—H8A109.0
N1—C1—H1A109.5N2—C8—H8B109.0
N1—C1—H1B109.5C9—C8—H8B109.0
H1A—C1—H1B109.5H8A—C8—H8B107.8
N1—C1—H1C109.5C14—C9—C10118.4 (9)
H1A—C1—H1C109.5C14—C9—C8120.8 (9)
H1B—C1—H1C109.5C10—C9—C8120.8 (8)
N1—C2—C3120.9 (8)C11—C10—C9120.0 (9)
N1—C2—H2A119.5C11—C10—H10120.0
C3—C2—H2A119.5C9—C10—H10120.0
C4—C3—C2120.0 (8)C10—C11—C12121.5 (10)
C4—C3—H3120.0C10—C11—H11119.3
C2—C3—H3120.0C12—C11—H11119.3
C3—C4—C5116.9 (9)C13—C12—C11118.7 (10)
C3—C4—C7123.9 (8)C13—C12—H12120.7
C5—C4—C7119.1 (8)C11—C12—H12120.7
C6—C5—C4121.4 (8)C14—C13—C12120.7 (10)
C6—C5—H5119.3C14—C13—H13119.6
C4—C5—H5119.3C12—C13—H13119.6
N1—C6—C5120.9 (8)C13—C14—C9120.6 (10)
N1—C6—H6119.6C13—C14—H14119.7
C5—C6—H6119.6C9—C14—H14119.7
C6—N1—C2—C30.4 (14)C3—C4—C7—N218.1 (13)
C1—N1—C2—C3179.7 (9)C5—C4—C7—N2164.0 (9)
N1—C2—C3—C42.5 (14)C7—N2—C8—C975.0 (11)
C2—C3—C4—C53.5 (13)N2—C8—C9—C14104.6 (9)
C2—C3—C4—C7178.6 (9)N2—C8—C9—C1077.6 (11)
C3—C4—C5—C62.7 (14)C14—C9—C10—C114.3 (13)
C7—C4—C5—C6179.3 (9)C8—C9—C10—C11177.8 (9)
C2—N1—C6—C50.5 (14)C9—C10—C11—C123.4 (15)
C1—N1—C6—C5178.9 (9)C10—C11—C12—C130.5 (15)
C4—C5—C6—N10.7 (16)C11—C12—C13—C141.3 (15)
C8—N2—C7—O12.3 (14)C12—C13—C14—C90.2 (15)
C8—N2—C7—C4176.2 (8)C10—C9—C14—C132.6 (13)
C3—C4—C7—O1160.5 (9)C8—C9—C14—C13179.5 (9)
C5—C4—C7—O117.4 (13)
Symmetry code: (i) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···I20.862.843.632 (7)154
C2—H2A···I2ii0.933.184.053 (9)158
C1—H1B···I2ii0.963.113.992 (9)153
C1—H1C···I2iii0.962.963.908 (9)171
C1—H1A···I1iv0.963.003.824 (10)145
C5—H5···O1v0.932.593.328 (11)136
C8—H8B···C11vi0.972.803.590 (15)140
C8—H8B···C10vi0.972.763.694 (14)162
Symmetry codes: (ii) x+1, y+1, z+1; (iii) x1/2, y+3/2, z1/2; (iv) x1/2, y+1/2, z1/2; (v) x, y+1, z+1; (vi) x+1/2, y1/2, z+3/2.
4-[(Benzylamino)carbonyl]-1-methylpyridinium triiodide (II) top
Crystal data top
C14H15N2O+·I3F(000) = 2242
Mr = 608.61Dx = 2.183 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.914 (2) ÅCell parameters from 1078 reflections
b = 27.805 (4) Åθ = 3.1–18.1°
c = 14.113 (3) ŵ = 5.07 mm1
β = 107.83 (2)°T = 293 K
V = 3703.4 (12) Å3Block, yellow
Z = 80.03 × 0.03 × 0.02 mm
Data collection top
Xcalibur, Sapphire3
diffractometer
6496 independent reflections
Radiation source: Enhance (Mo) X-ray Source2548 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm-1Rint = 0.124
ω scansθmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2018)
h = 811
Tmin = 0.347, Tmax = 1.000k = 3333
21040 measured reflectionsl = 1616
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.065H-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 reflectionsΔρmax = 0.70 e Å3
371 parametersΔρmin = 0.77 e Å3
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
xyzUiso*/UeqOcc. (<1)
I10.45921 (12)0.79328 (4)0.65364 (9)0.0868 (4)
I20.46503 (14)0.71598 (5)0.78702 (11)0.1072 (4)
I30.45434 (15)0.87375 (4)0.50883 (10)0.1061 (5)
I40.0000001.0000000.5000000.1048 (6)
I50.09620 (18)0.93095 (5)0.62111 (13)0.1313 (6)
I60.4785 (8)0.5112 (2)0.5262 (5)0.130 (2)0.5
I70.3252 (7)0.5746 (2)0.6849 (5)0.1504 (17)0.5
I7A0.3531 (7)0.5527 (2)0.6302 (5)0.1504 (17)0.5
O1A0.1281 (11)0.6399 (4)0.3910 (8)0.092 (3)
N1A0.0042 (18)0.8083 (4)0.3781 (10)0.081 (4)
N2A0.0997 (12)0.6306 (4)0.4111 (9)0.078 (4)
H2A0.1755860.6431980.4046940.094*
C1A0.004 (2)0.8621 (5)0.3785 (13)0.110 (6)
H1AA0.0915080.8735320.3494460.165*
H1AB0.0397440.8735270.4457620.165*
H1AC0.0622840.8738110.3405570.165*
C2A0.1245 (19)0.7843 (6)0.4148 (13)0.096 (5)
H2AA0.2093430.8010510.4387590.115*
C3A0.1251 (16)0.7345 (6)0.4178 (12)0.088 (5)
H3A0.2102050.7177860.4409840.106*
C4A0.0012 (16)0.7105 (6)0.3867 (12)0.079 (4)
C5A0.1202 (19)0.7349 (6)0.3482 (12)0.089 (5)
H5A0.2056550.7184590.3249950.107*
C6A0.1183 (19)0.7837 (7)0.3431 (13)0.095 (5)
H6A0.2025050.8003790.3150600.114*
C7A0.0134 (16)0.6579 (6)0.3940 (11)0.079 (4)
C8A0.1044 (17)0.5796 (5)0.4403 (13)0.092 (5)
H8AA0.1815840.5640570.4234950.110*
H8AB0.0169590.5642550.4016880.110*
C9A0.1238 (18)0.5715 (5)0.5504 (12)0.074 (4)
C10A0.252 (2)0.5902 (6)0.6130 (16)0.097 (6)
H10A0.3161060.6054990.5871260.117*
C11A0.279 (2)0.5848 (6)0.7157 (17)0.106 (6)
H11A0.3601080.5976690.7601620.128*
C12A0.184 (2)0.5606 (7)0.7493 (16)0.106 (6)
H12A0.2036000.5549330.8171300.127*
C13A0.060 (2)0.5444 (6)0.685 (2)0.107 (7)
H13A0.0053240.5295270.7109070.128*
C14A0.027 (2)0.5491 (7)0.5838 (17)0.121 (7)
H14A0.0579240.5375760.5407000.145*
O1B0.3841 (10)0.6543 (4)0.4242 (8)0.086 (3)
N1B0.4543 (16)0.5322 (5)0.1922 (12)0.088 (4)
N2B0.6125 (12)0.6628 (4)0.4475 (8)0.076 (4)
H2B0.6845950.6550030.4291310.091*
C1B0.4388 (19)0.4928 (6)0.1164 (14)0.108 (6)
H1BA0.5307470.4807080.1196420.162*
H1BB0.3824010.4672820.1301340.162*
H1BC0.3933750.5054620.0510880.162*
C2B0.581 (2)0.5433 (6)0.2527 (16)0.102 (6)
H2BA0.6589940.5252930.2505890.123*
C3B0.5997 (15)0.5805 (5)0.3180 (12)0.074 (4)
H3B0.6909850.5892530.3555990.088*
C4B0.4836 (14)0.6059 (5)0.3296 (11)0.069 (4)
C5B0.356 (2)0.5904 (6)0.2686 (12)0.089 (5)
H5B0.2739940.6052030.2729630.107*
C6B0.3436 (18)0.5548 (6)0.2030 (12)0.090 (5)
H6B0.2535720.5457490.1635280.107*
C7B0.4904 (17)0.6428 (5)0.4034 (11)0.071 (4)
C8B0.6312 (18)0.6988 (5)0.5285 (12)0.085 (5)
H8BA0.5699280.7261280.5027820.102*
H8BB0.6011060.6845950.5814910.102*
C9B0.7765 (16)0.7161 (6)0.5702 (11)0.072 (4)
C10B0.8890 (17)0.6853 (6)0.6049 (12)0.084 (4)
H10B0.8721790.6523120.6012740.100*
C11B1.024 (2)0.7013 (7)0.6443 (13)0.097 (5)
H11B1.0974430.6793750.6688210.116*
C12B1.0525 (19)0.7495 (8)0.6480 (11)0.094 (5)
H12B1.1446600.7604300.6766790.112*
C13B0.946 (2)0.7812 (7)0.6098 (13)0.096 (5)
H13B0.9661270.8138240.6081680.115*
C14B0.8040 (16)0.7646 (6)0.5720 (11)0.081 (5)
H14B0.7301160.7863630.5487350.097*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0752 (7)0.0882 (8)0.0963 (8)0.0041 (6)0.0254 (6)0.0169 (6)
I20.0868 (9)0.0985 (9)0.1316 (11)0.0025 (7)0.0264 (8)0.0075 (8)
I30.1210 (11)0.0961 (9)0.0995 (9)0.0168 (8)0.0312 (8)0.0034 (7)
I40.0852 (12)0.0960 (13)0.1177 (14)0.0118 (10)0.0082 (10)0.0004 (10)
I50.1384 (14)0.1108 (11)0.1504 (14)0.0019 (10)0.0526 (12)0.0023 (9)
I60.099 (4)0.131 (5)0.180 (7)0.027 (3)0.072 (5)0.077 (4)
I70.117 (3)0.148 (4)0.200 (6)0.001 (3)0.069 (4)0.048 (3)
I7A0.117 (3)0.148 (4)0.200 (6)0.001 (3)0.069 (4)0.048 (3)
O1A0.068 (7)0.091 (8)0.123 (10)0.009 (6)0.039 (7)0.023 (6)
N1A0.106 (11)0.062 (8)0.085 (9)0.004 (8)0.043 (9)0.012 (7)
N2A0.048 (7)0.080 (9)0.105 (10)0.015 (7)0.022 (7)0.018 (7)
C1A0.137 (18)0.073 (11)0.116 (15)0.004 (11)0.031 (13)0.013 (10)
C2A0.071 (12)0.091 (13)0.124 (15)0.013 (10)0.029 (11)0.002 (11)
C3A0.058 (10)0.079 (11)0.115 (14)0.002 (9)0.008 (9)0.013 (9)
C4A0.048 (9)0.093 (12)0.086 (11)0.011 (9)0.005 (8)0.001 (9)
C5A0.085 (13)0.089 (13)0.087 (12)0.024 (11)0.018 (10)0.002 (9)
C6A0.069 (11)0.121 (16)0.098 (13)0.017 (12)0.031 (10)0.017 (11)
C7A0.050 (9)0.110 (14)0.076 (11)0.004 (10)0.021 (8)0.010 (9)
C8A0.078 (12)0.075 (11)0.125 (16)0.011 (9)0.035 (11)0.017 (10)
C9A0.080 (11)0.064 (10)0.067 (11)0.006 (8)0.009 (9)0.018 (8)
C10A0.108 (15)0.081 (12)0.122 (16)0.001 (11)0.063 (14)0.017 (11)
C11A0.087 (14)0.105 (15)0.125 (18)0.001 (11)0.029 (13)0.021 (12)
C12A0.094 (15)0.113 (16)0.112 (16)0.024 (13)0.034 (14)0.002 (12)
C13A0.114 (17)0.074 (12)0.16 (2)0.003 (12)0.084 (17)0.024 (13)
C14A0.125 (18)0.140 (18)0.120 (19)0.011 (15)0.072 (16)0.011 (14)
O1B0.058 (7)0.107 (8)0.098 (8)0.007 (6)0.029 (6)0.016 (6)
N1B0.087 (10)0.073 (9)0.120 (12)0.009 (8)0.058 (10)0.002 (8)
N2B0.042 (7)0.105 (10)0.078 (9)0.011 (7)0.014 (6)0.018 (7)
C1B0.105 (15)0.101 (13)0.120 (15)0.017 (11)0.036 (13)0.017 (12)
C2B0.075 (13)0.060 (11)0.18 (2)0.006 (10)0.048 (14)0.007 (12)
C3B0.056 (9)0.054 (9)0.109 (13)0.012 (7)0.021 (9)0.012 (8)
C4B0.043 (8)0.073 (10)0.086 (11)0.010 (7)0.011 (7)0.005 (8)
C5B0.113 (15)0.084 (12)0.085 (12)0.011 (11)0.054 (12)0.009 (9)
C6B0.072 (11)0.116 (15)0.081 (12)0.019 (11)0.023 (10)0.007 (10)
C7B0.073 (10)0.075 (10)0.077 (11)0.015 (9)0.038 (9)0.005 (8)
C8B0.094 (13)0.075 (10)0.086 (11)0.011 (9)0.028 (10)0.014 (9)
C9B0.068 (10)0.077 (11)0.075 (10)0.012 (9)0.030 (8)0.018 (8)
C10B0.066 (11)0.089 (12)0.089 (12)0.011 (10)0.014 (9)0.003 (9)
C11B0.077 (13)0.125 (16)0.092 (13)0.005 (12)0.030 (11)0.003 (11)
C12B0.072 (12)0.140 (17)0.064 (11)0.021 (13)0.014 (9)0.016 (11)
C13B0.090 (13)0.104 (13)0.097 (13)0.006 (12)0.034 (11)0.002 (11)
C14B0.052 (9)0.112 (14)0.069 (10)0.014 (9)0.005 (8)0.014 (9)
Geometric parameters (Å, º) top
I1—I22.8459 (18)C12A—H12A0.9300
I1—I33.0206 (17)C13A—C14A1.37 (3)
I4—I52.9181 (15)C13A—H13A0.9300
I4—I5i2.9181 (15)C14A—H14A0.9300
I6—I6ii0.962 (9)O1B—C7B1.220 (15)
I6—I7A1.977 (7)N1B—C6B1.313 (18)
I6—I72.890 (7)N1B—C2B1.32 (2)
I6—I7Aii2.925 (7)N1B—C1B1.504 (19)
I7—I7A0.957 (7)N2B—C7B1.305 (17)
O1A—C7A1.231 (16)N2B—C8B1.488 (17)
N1A—C2A1.327 (19)N2B—H2B0.8600
N1A—C6A1.35 (2)C1B—H1BA0.9600
N1A—C1A1.495 (17)C1B—H1BB0.9600
N2A—C7A1.315 (17)C1B—H1BC0.9600
N2A—C8A1.472 (17)C2B—C3B1.36 (2)
N2A—H2A0.8600C2B—H2BA0.9300
C1A—H1AA0.9600C3B—C4B1.403 (18)
C1A—H1AB0.9600C3B—H3B0.9300
C1A—H1AC0.9600C4B—C5B1.36 (2)
C2A—C3A1.39 (2)C4B—C7B1.447 (19)
C2A—H2AA0.9300C5B—C6B1.335 (19)
C3A—C4A1.348 (19)C5B—H5B0.9300
C3A—H3A0.9300C6B—H6B0.9300
C4A—C5A1.34 (2)C8B—C9B1.46 (2)
C4A—C7A1.48 (2)C8B—H8BA0.9700
C5A—C6A1.36 (2)C8B—H8BB0.9700
C5A—H5A0.9300C9B—C10B1.372 (19)
C6A—H6A0.9300C9B—C14B1.374 (19)
C8A—C9A1.52 (2)C10B—C11B1.36 (2)
C8A—H8AA0.9700C10B—H10B0.9300
C8A—H8AB0.9700C11B—C12B1.37 (2)
C9A—C14A1.35 (2)C11B—H11B0.9300
C9A—C10A1.40 (2)C12B—C13B1.35 (2)
C10A—C11A1.40 (2)C12B—H12B0.9300
C10A—H10A0.9300C13B—C14B1.42 (2)
C11A—C12A1.35 (2)C13B—H13B0.9300
C11A—H11A0.9300C14B—H14B0.9300
C12A—C13A1.36 (3)
I2—I1—I3178.72 (5)C12A—C13A—C14A122.8 (18)
I5—I4—I5i180.0C12A—C13A—H13A118.6
I6ii—I6—I7A168.1 (11)C14A—C13A—H13A118.6
I6ii—I6—I7174.9 (11)C9A—C14A—C13A116 (2)
I7A—I6—I76.9 (3)C9A—C14A—H14A121.9
I6ii—I6—I7Aii8.0 (8)C13A—C14A—H14A121.9
I7A—I6—I7Aii176.1 (4)C6B—N1B—C2B118.4 (15)
I7—I6—I7Aii176.9 (4)C6B—N1B—C1B121.6 (16)
I7A—I7—I614.4 (7)C2B—N1B—C1B120.0 (15)
I7—I7A—I6158.7 (10)C7B—N2B—C8B122.2 (12)
I7—I7A—I6ii162.5 (9)C7B—N2B—H2B118.9
I6—I7A—I6ii3.9 (4)C8B—N2B—H2B118.9
C2A—N1A—C6A119.2 (14)N1B—C1B—H1BA109.5
C2A—N1A—C1A120.4 (16)N1B—C1B—H1BB109.5
C6A—N1A—C1A120.3 (16)H1BA—C1B—H1BB109.5
C7A—N2A—C8A124.0 (13)N1B—C1B—H1BC109.5
C7A—N2A—H2A118.0H1BA—C1B—H1BC109.5
C8A—N2A—H2A118.0H1BB—C1B—H1BC109.5
N1A—C1A—H1AA109.5N1B—C2B—C3B121.5 (16)
N1A—C1A—H1AB109.5N1B—C2B—H2BA119.3
H1AA—C1A—H1AB109.5C3B—C2B—H2BA119.3
N1A—C1A—H1AC109.5C2B—C3B—C4B121.0 (15)
H1AA—C1A—H1AC109.5C2B—C3B—H3B119.5
H1AB—C1A—H1AC109.5C4B—C3B—H3B119.5
N1A—C2A—C3A120.7 (16)C5B—C4B—C3B113.7 (14)
N1A—C2A—H2AA119.6C5B—C4B—C7B120.6 (14)
C3A—C2A—H2AA119.6C3B—C4B—C7B125.5 (14)
C4A—C3A—C2A119.3 (16)C6B—C5B—C4B122.9 (16)
C4A—C3A—H3A120.3C6B—C5B—H5B118.5
C2A—C3A—H3A120.3C4B—C5B—H5B118.5
C5A—C4A—C3A119.7 (16)N1B—C6B—C5B122.2 (17)
C5A—C4A—C7A115.8 (14)N1B—C6B—H6B118.9
C3A—C4A—C7A124.5 (15)C5B—C6B—H6B118.9
C4A—C5A—C6A120.1 (17)O1B—C7B—N2B121.1 (14)
C4A—C5A—H5A120.0O1B—C7B—C4B120.4 (15)
C6A—C5A—H5A120.0N2B—C7B—C4B118.6 (13)
N1A—C6A—C5A120.8 (17)C9B—C8B—N2B113.9 (13)
N1A—C6A—H6A119.6C9B—C8B—H8BA108.8
C5A—C6A—H6A119.6N2B—C8B—H8BA108.8
O1A—C7A—N2A119.8 (16)C9B—C8B—H8BB108.8
O1A—C7A—C4A120.7 (14)N2B—C8B—H8BB108.8
N2A—C7A—C4A119.3 (14)H8BA—C8B—H8BB107.7
N2A—C8A—C9A114.4 (12)C10B—C9B—C14B118.1 (15)
N2A—C8A—H8AA108.7C10B—C9B—C8B122.2 (15)
C9A—C8A—H8AA108.7C14B—C9B—C8B119.6 (15)
N2A—C8A—H8AB108.7C11B—C10B—C9B122.2 (17)
C9A—C8A—H8AB108.7C11B—C10B—H10B118.9
H8AA—C8A—H8AB107.6C9B—C10B—H10B118.9
C14A—C9A—C10A123.7 (18)C10B—C11B—C12B120.2 (18)
C14A—C9A—C8A123.0 (17)C10B—C11B—H11B119.9
C10A—C9A—C8A113.2 (16)C12B—C11B—H11B119.9
C11A—C10A—C9A117.4 (17)C13B—C12B—C11B119.9 (18)
C11A—C10A—H10A121.3C13B—C12B—H12B120.1
C9A—C10A—H10A121.3C11B—C12B—H12B120.1
C12A—C11A—C10A119 (2)C12B—C13B—C14B119.9 (17)
C12A—C11A—H11A120.5C12B—C13B—H13B120.1
C10A—C11A—H11A120.5C14B—C13B—H13B120.1
C11A—C12A—C13A121 (2)C9B—C14B—C13B119.6 (16)
C11A—C12A—H12A119.6C9B—C14B—H14B120.2
C13A—C12A—H12A119.6C13B—C14B—H14B120.2
I6—I7—I7A—I6ii2.0 (11)C6B—N1B—C2B—C3B7 (3)
C6A—N1A—C2A—C3A0 (2)C1B—N1B—C2B—C3B176.0 (14)
C1A—N1A—C2A—C3A177.8 (15)N1B—C2B—C3B—C4B6 (3)
N1A—C2A—C3A—C4A3 (3)C2B—C3B—C4B—C5B2 (2)
C2A—C3A—C4A—C5A4 (3)C2B—C3B—C4B—C7B173.6 (15)
C2A—C3A—C4A—C7A174.6 (15)C3B—C4B—C5B—C6B1 (2)
C3A—C4A—C5A—C6A2 (3)C7B—C4B—C5B—C6B176.4 (14)
C7A—C4A—C5A—C6A176.7 (14)C2B—N1B—C6B—C5B4 (3)
C2A—N1A—C6A—C5A2 (2)C1B—N1B—C6B—C5B178.7 (15)
C1A—N1A—C6A—C5A175.8 (14)C4B—C5B—C6B—N1B0 (3)
C4A—C5A—C6A—N1A1 (2)C8B—N2B—C7B—O1B3 (2)
C8A—N2A—C7A—O1A8 (2)C8B—N2B—C7B—C4B176.2 (13)
C8A—N2A—C7A—C4A166.8 (14)C5B—C4B—C7B—O1B13 (2)
C5A—C4A—C7A—O1A19 (2)C3B—C4B—C7B—O1B161.8 (15)
C3A—C4A—C7A—O1A159.5 (17)C5B—C4B—C7B—N2B167.7 (14)
C5A—C4A—C7A—N2A166.0 (15)C3B—C4B—C7B—N2B18 (2)
C3A—C4A—C7A—N2A16 (2)C7B—N2B—C8B—C9B178.3 (14)
C7A—N2A—C8A—C9A81 (2)N2B—C8B—C9B—C10B53 (2)
N2A—C8A—C9A—C14A117.5 (17)N2B—C8B—C9B—C14B124.6 (15)
N2A—C8A—C9A—C10A61.6 (18)C14B—C9B—C10B—C11B3 (2)
C14A—C9A—C10A—C11A0 (3)C8B—C9B—C10B—C11B179.5 (15)
C8A—C9A—C10A—C11A179.4 (14)C9B—C10B—C11B—C12B2 (3)
C9A—C10A—C11A—C12A2 (3)C10B—C11B—C12B—C13B2 (3)
C10A—C11A—C12A—C13A4 (3)C11B—C12B—C13B—C14B4 (2)
C11A—C12A—C13A—C14A4 (3)C10B—C9B—C14B—C13B0 (2)
C10A—C9A—C14A—C13A1 (3)C8B—C9B—C14B—C13B178.0 (14)
C8A—C9A—C14A—C13A179.8 (15)C12B—C13B—C14B—C9B3 (2)
C12A—C13A—C14A—C9A1 (3)
Symmetry codes: (i) x, y+2, z+1; (ii) x1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2A···O1B0.862.022.846 (14)160
C3A—H3A···O1B0.932.533.381 (18)152
C2A—H2AA···I30.933.083.998 (17)169
C1A—H1AC···C12Aiii0.962.723.62 (2)158
C1A—H1AA···I7iii0.963.093.966 (19)153
N2B—H2B···O1Aiv0.862.132.986 (14)176
C3B—H3B···O1Aiv0.932.213.060 (17)151
C2B—H2BA···C12Av0.932.853.72 (2)156
C1B—H1BB···I7vi0.963.073.819 (18)136
C6B—H6B···I4vii0.933.124.019 (17)164
Symmetry codes: (iii) x, y+3/2, z1/2; (iv) x+1, y, z; (v) x+1, y+1, z+1; (vi) x, y+1, z+1; (vii) x, y1/2, z+1/2.
Selected geometrical parameters (Å, °) for the cations in salts I and II top
ParameterIIIAIIB
N1—C21.338 (10)1.327 (19)1.32 (2)
N1—C61.324 (11)1.35 (2)1.313 (18)
N2—C7—C4—C318.1 (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···H32.092.142.11
C3···H22.552.612.57
 

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