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_7704443
_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 H12 Cl4 N2 O2'
_chemical_formula_sum            'C20 H12 Cl4 N2 O2'
_chemical_formula_weight         454.12
_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     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                 104.946(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.0305(13)
_cell_length_b                   4.7498(3)
_cell_length_c                   21.7414(16)
_cell_measurement_reflns_used    5564
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.4150
_cell_measurement_theta_min      1.6880
_cell_volume                     1898.7(2)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170(2)
_diffrn_detector                 'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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    -60.00 120.00   1.00   16.00    --   30.00  54.00   0.00  180
  2  \w    -60.00 120.00   1.00   16.00    --   30.00  54.00 120.00  180
  3  \w    -60.00 120.00   1.00   16.00    --   30.00  54.00 240.00  180
;
_diffrn_measurement_device       'XtaLAB AFC11 (RCD3)'
_diffrn_measurement_device_type
'XtaLAB AFC11 (RCD3) equipped with fine-focus (Mo) sealed X-ray tube, quarter-chi goniometer and CCD detector'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0243162000
_diffrn_orient_matrix_UB_12      -0.0310220000
_diffrn_orient_matrix_UB_13      0.0194461000
_diffrn_orient_matrix_UB_21      0.0300661000
_diffrn_orient_matrix_UB_22      0.0010357000
_diffrn_orient_matrix_UB_23      0.0278204000
_diffrn_orient_matrix_UB_31      -0.0053049000
_diffrn_orient_matrix_UB_32      0.1479375000
_diffrn_orient_matrix_UB_33      0.0039076000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0861
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17918
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.142
_diffrn_reflns_theta_min         1.649
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
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    1.589
_exptl_crystal_description       needle
_exptl_crystal_F_000             920
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of DMF and diethyl ether  by slow diffusion'
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0324P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0972
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2654
_reflns_number_total             4187
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0dt01492c2.cif
_cod_data_source_block           rm46_2_aco
_cod_depositor_comments
'Adding full bibliography for 7704441--7704445.cif.'
_cod_database_code               7704443
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C38 H51 Cl4 N3 O4 '
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.866
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C5(H5), C10(H10), C12(H12), C13(H13), C17(H17),
 C19(H19), C20(H20)
;
_shelx_res_checksum              55265
_olex2_date_sample_data_collection 2015-06-05
_olex2_date_sample_submission    2015-06-05
_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 L4
_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 1.073
_oxdiff_exptl_absorpt_empirical_full_min 0.931