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_7704444
_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         'C19 H13 I2 N3 O2'
_chemical_formula_sum            'C19 H13 I2 N3 O2'
_chemical_formula_weight         569.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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                 93.3100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.2221(2)
_cell_length_b                   16.2083(10)
_cell_length_c                   26.3584(17)
_cell_measurement_reflns_used    5653
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.0
_cell_volume                     1800.78(18)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
scan:
	Number of images: 151
	           Slice: -77.0000 - 74.0000
	     Image width: 1.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 18.0000
	             Phi: -120.0000
	             XTD: 44.8843
	          2theta: -15.7904
scan:
	Number of images: 95
	           Slice: -82.0000 - 13.0000
	     Image width: 1.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 60.0000
	             XTD: 44.8843
	          2theta: -15.7904
scan:
	Number of images: 66
	           Slice: -44.0000 - 22.0000
	     Image width: 1.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: -60.0000
	             XTD: 44.8843
	          2theta: -15.7904
scan:
	Number of images: 52
	           Slice: -41.0000 - 11.0000
	     Image width: 1.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: -180.0000
	             XTD: 44.8843
	          2theta: -15.7904
scan:
	Number of images: 42
	           Slice: -58.0000 - -16.0000
	     Image width: 1.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 0.0000
	             XTD: 44.8843
	          2theta: -15.7904
scan:
	Number of images: 25
	           Slice: -84.0000 - -59.0000
	     Image width: 1.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -54.0000
	             Phi: 60.0000
	             XTD: 44.8843
	          2theta: -15.7904
scan:
	Number of images: 105
	           Slice: -97.0000 - 8.0000
	     Image width: 1.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -36.0000
	             Phi: 60.0000
	             XTD: 44.8843
	          2theta: -15.7904
scan:
	Number of images: 26
	           Slice: -79.0000 - -53.0000
	     Image width: 1.0000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: -150.0000
	             XTD: 44.8843
	          2theta: -15.7904
;
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku FRE-HF'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.236223
_diffrn_orient_matrix_UB_12      0.015004
_diffrn_orient_matrix_UB_13      0.016085
_diffrn_orient_matrix_UB_21      0.005644
_diffrn_orient_matrix_UB_22      -0.048696
_diffrn_orient_matrix_UB_23      -0.037461
_diffrn_orient_matrix_UB_31      0.002758
_diffrn_orient_matrix_UB_32      0.023310
_diffrn_orient_matrix_UB_33      -0.029886
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, HF 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_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            23996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.451
_diffrn_reflns_theta_min         1.994
_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    3.512
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.099
_exptl_crystal_description       needle
_exptl_crystal_F_000             1080
_exptl_crystal_recrystallization_method
'The material was recrystallised from chloroform'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4122
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0204
_refine_ls_R_factor_gt           0.0188
_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^)+(0.0216P)^2^+1.7746P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0448
_refine_ls_wR_factor_ref         0.0458
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3916
_reflns_number_total             4122
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0dt01492c2.cif
_cod_data_source_block           2015cag0008
_cod_depositor_comments
'Adding full bibliography for 7704441--7704445.cif.'
_cod_database_code               7704444
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 N3-H3A = N2-H2A
 0.88 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C15(H15),
 C16(H16), C17(H17), C18(H18)
;
_shelx_res_checksum              88173
_olex2_date_sample_data_collection 2015-03-05
_olex2_date_sample_submission    2015-02-05
_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 L2
_olex2_submission_special_instructions 'No special instructions were received'