Halogenated isophthalamides and dipicolineamides: the role of the halogen substituents in the anion binding properties.
Picci, Giacomo; Bazzicalupi, Carla; Coles, Simon J.; Gratteri, Paola; Isaia, Francesco; Lippolis, Vito; Montis, Riccardo; Murgia, Sergio; Nocentini, Alessio; Orton, James B.; Caltagirone, Claudia; Dalton transactions (Cambridge, England : 2003) 49 (2020) 9231–9238; doi:10.1039/d0dt01492c

data_7704441
_publ_section_title
;
 Halogenated isophthalamides and dipicolineamides: the role of the halogen
 substituents in the anion binding properties.
;
_journal_issue                   27
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              9231
_journal_page_last               9238
_journal_paper_doi               10.1039/d0dt01492c
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C20 H14 I2 N2 O2'
_chemical_formula_sum            'C20 H14 I2 N2 O2'
_chemical_formula_weight         568.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-04-07 deposited with the CCDC.	2020-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.372(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.3177(9)
_cell_length_b                   4.76320(10)
_cell_length_c                   22.0266(9)
_cell_measurement_reflns_used    10836
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5630
_cell_measurement_theta_min      2.3280
_cell_volume                     1831.27(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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    -66.00  68.00   1.00    7.00    --  -22.00  72.00 -90.00  134
  2  \w    -99.00  36.00   1.00    7.00    --  -22.00 -18.00 -60.00  135
  3  \w    -63.00  15.00   1.00    7.00    --  -22.00 -72.00  90.00   78
  4  \w    -35.00  22.00   1.00    7.00    --  -22.00 -72.00 -60.00   57
  5  \w    -60.00  -2.00   1.00    7.00    --  -22.00 -72.00-180.00   58
  6  \w    -62.00 -37.00   1.00    7.00    --  -22.00 -54.00  30.00   25
  7  \w   -112.00 -13.00   1.00    7.00    --  -22.00 -72.00 120.00   99
  8  \w    -66.00  30.00   1.00    7.00    --  -22.00  72.00-120.00   96
  9  \w    -87.00 -61.00   1.00    7.00    --  -22.00  18.00  90.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC12 \k goniometer'
_diffrn_measurement_device_type
'Rigaku FRE+ equipped with VHF Varimax confocal mirrors, an AFC12 goniometer and Rigaku HG Saturn724+ detector'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0393294000
_diffrn_orient_matrix_UB_12      -0.0122955000
_diffrn_orient_matrix_UB_13      0.0225276000
_diffrn_orient_matrix_UB_21      -0.0021890000
_diffrn_orient_matrix_UB_22      -0.1477129000
_diffrn_orient_matrix_UB_23      -0.0043978000
_diffrn_orient_matrix_UB_31      0.0100406000
_diffrn_orient_matrix_UB_32      0.0139477000
_diffrn_orient_matrix_UB_33      -0.0272754000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            6273
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.638
_diffrn_reflns_theta_min         2.334
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    3.452
_exptl_absorpt_correction_T_max  0.17156
_exptl_absorpt_correction_T_min  0.14930
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Spherical absorption correction
 using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light brown'
_exptl_crystal_colour_primary    'light brown'
_exptl_crystal_density_diffrn    2.061
_exptl_crystal_description       needle
_exptl_crystal_F_000             1080
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of methanol and chloroform  by slow diffusion'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.001
_exptl_crystal_size_rad          0.400
_refine_diff_density_max         1.543
_refine_diff_density_min         -1.090
_refine_diff_density_rms         0.201
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         6273
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0342P)^2^+19.7951P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1081
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5708
_reflns_number_total             6273
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 179.7806\% 
 around [1.00 -0.00 0.00] (reciprocal) or [0.94 -0.01 0.35] (direct)
;
_cod_data_source_file            d0dt01492c2.cif
_cod_data_source_block           2015cag0003_t3a_twin1_hklf4
_cod_depositor_comments
'Adding full bibliography for 7704441--7704445.cif.'
_cod_database_code               7704441
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H14 I2 N2 O2'
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.517
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.8127(8)
 0.1873(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
3. Restrained distances
 N1-H1A = N2-H2
 0.88 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C17(H17), C18(H18), C19(H19), C20(H20)
;
_shelx_res_checksum              19375
_olex2_date_sample_data_collection 2015-01-31
_olex2_date_sample_submission    2015-01-31
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id L1
_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 2.203
_oxdiff_exptl_absorpt_empirical_full_min 0.424
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2