Dihypoiodites Stabilised by 4-ethylpyridine through O-I-N Halogen Bonds
Kramer, Eric; Yu, Shilin; Ward, Jas S.; Rissanen, Kari; Dalton Transactions  (2021) –; doi:10.1039/D1DT03324G

data_7708567
_publ_section_title
;
 Dihypoiodites Stabilised by 4-ethylpyridine through O-I-N Halogen Bonds
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D1DT03324G
_journal_year                    2021
_chemical_formula_moiety         'C22 H22 I2 N2 O4'
_chemical_formula_sum            'C22 H22 I2 N2 O4'
_chemical_formula_weight         632.21
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-24 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                84.321(8)
_cell_angle_beta                 87.332(8)
_cell_angle_gamma                71.188(6)
_cell_formula_units_Z            2
_cell_length_a                   8.0109(5)
_cell_length_b                   9.0287(6)
_cell_length_c                   16.548(2)
_cell_measurement_reflns_used    3812
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      75.0000
_cell_measurement_theta_min      2.6210
_cell_volume                     1127.25(18)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -115.00 -13.00   1.00    5.00    --  -41.40 -57.00  30.00  102
  2  \w   -115.00 -13.00   1.00    5.00    --  -41.40 -57.00 120.00  102
  3  \w    -70.00  32.00   1.00    5.00    --  -41.40  57.00 -90.00  102
  4  \w      6.00  82.00   1.00    5.00    --   41.40 -99.00 -30.00   76
  5  \w     84.00 178.00   1.00   25.00    --  112.00  30.00 -30.00   94
  6  \w     36.00 109.00   1.00   25.00    --  112.00-111.00   0.00   73
  7  \w     40.00 141.00   1.00   25.00    --  112.00 -61.00-180.00  101
  8  \w     36.00 140.00   1.00   25.00    --  112.00 -30.00   0.00  104
  9  \w     29.00 107.00   1.00   25.00    --  112.00 -94.00 150.00   78
 10  \w    103.00 178.00   1.00   25.00    --  112.00  77.00 -60.00   75
 11  \w     36.00 109.00   1.00   25.00    --  112.00-111.00  60.00   73
 12  \w     39.00 138.00   1.00   25.00    --  112.00 -45.00 -90.00   99
 13  \w     36.00 109.00   1.00   25.00    --  112.00-111.00 -60.00   73
 14  \w     59.00 178.00   1.00   25.00    --  112.00  15.00 -90.00  119
 15  \w     61.00 146.00   1.00   25.00    --  112.00 178.00-180.00   85
 16  \w   -115.00 -13.00   1.00    5.00    --  -41.40 -57.00 -90.00  102
 17  \w    -86.00  -6.00   1.00    5.00    --  -41.40 125.00  60.00   80
 18  \w   -116.00 -17.00   1.00    5.00    --  -41.40 -37.00-180.00   99
 19  \w      6.00  32.00   1.00    5.00    --   41.40  85.00 -95.89   26
 20  \w     84.00 178.00   1.00   25.00    --  112.00  30.00 150.00   94
 21  \w     80.00 121.00   1.00   25.00    --  112.00  73.00  -7.68   41
 22  \w     84.00 178.00   1.00   25.00    --  112.00  30.00  60.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1895537000
_diffrn_orient_matrix_UB_12      0.0072678000
_diffrn_orient_matrix_UB_13      -0.0004446000
_diffrn_orient_matrix_UB_21      -0.0067453000
_diffrn_orient_matrix_UB_22      0.0380415000
_diffrn_orient_matrix_UB_23      -0.0928587000
_diffrn_orient_matrix_UB_31      -0.0728556000
_diffrn_orient_matrix_UB_32      0.1767808000
_diffrn_orient_matrix_UB_33      0.0114966000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1200
_diffrn_reflns_av_unetI/netI     0.1121
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12079
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.117
_diffrn_reflns_theta_min         2.684
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    22.170
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.863
_exptl_crystal_description       plate
_exptl_crystal_F_000             612
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.059
_exptl_crystal_size_min          0.013
_refine_diff_density_max         2.110
_refine_diff_density_min         -1.524
_refine_diff_density_rms         0.276
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4411
_refine_ls_number_restraints     222
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0818
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1441P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2177
_refine_ls_wR_factor_ref         0.2436
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3134
_reflns_number_total             4411
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt03324g2.cif
_cod_data_source_block           2
_cod_original_cell_volume        1127.23(18)
_cod_database_code               7708567
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.24
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
N11 \\sim N41 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim
C18 \\sim C42 \\sim C43 \\sim C44 \\sim C45 \\sim C46 \\sim C47 \\sim C48:
within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
3. Others
 Sof(C44)=Sof(C45)=Sof(H45)=Sof(C46)=Sof(H46)=Sof(N41)=Sof(C42)=Sof(H42)=
 Sof(C43)=Sof(H43)=Sof(C47)=Sof(H47A)=Sof(H47B)=Sof(C48)=Sof(H48A)=Sof(H48B)=
 Sof(H48C)=1-FVAR(1)
 Sof(C14)=Sof(C13)=Sof(H13)=Sof(C12)=Sof(H12)=Sof(N11)=Sof(C16)=Sof(H16)=
 Sof(C15)=Sof(H15)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(C18)=Sof(H18A)=Sof(H18B)=
 Sof(H18C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C17(H17A,H17B), C47(H47A,H47B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C12(H12), C16(H16), C15(H15),
 C22(H22), C24(H24), C25(H25), C26(H26), C45(H45), C46(H46), C42(H42), C43(H43)
4.c Fitted hexagon refined as free rotating group:
 C14(C13,C12,N11,C16,C15), C44(C45,C46,N41,C42,C43)
4.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C18(H18A,H18B,H18C), C48(H48A,H48B,H48C)
;
_shelx_res_checksum              19885
_shelx_hkl_checksum              73241
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.637
_oxdiff_exptl_absorpt_empirical_full_min 0.337