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_7704442
_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         '2(C10 H3 F5 N O)'
_chemical_formula_sum            'C20 H6 F10 N2 O2'
_chemical_formula_weight         496.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-07 deposited with the CCDC.	2020-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.837(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9136(2)
_cell_length_b                   35.5239(12)
_cell_length_c                   7.4234(2)
_cell_measurement_reflns_used    9595
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.1010
_cell_measurement_theta_min      2.2460
_cell_volume                     1810.21(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.18b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.18b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.18b (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.950
_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    -84.00  52.00   0.50    3.00    --    5.00 -38.00   0.00  272
  2  \w    -98.00  39.00   0.50    3.00    --   -8.80 -38.00-180.00  274
  3  \w    -84.00  -5.00   0.50    3.00    --    5.00 -57.00 -90.00  158
;
_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 and an AFC12 goniometer and HyPix 6000 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      0.0057441000
_diffrn_orient_matrix_UB_12      -0.0192508000
_diffrn_orient_matrix_UB_13      -0.0244297000
_diffrn_orient_matrix_UB_21      -0.1024828000
_diffrn_orient_matrix_UB_22      -0.0004597000
_diffrn_orient_matrix_UB_23      -0.0233100000
_diffrn_orient_matrix_UB_31      0.0118495000
_diffrn_orient_matrix_UB_32      0.0053136000
_diffrn_orient_matrix_UB_33      -0.0900695000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17034
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         2.293
_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    0.188
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.537
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.18b (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.821
_exptl_crystal_description       rod
_exptl_crystal_F_000             984
_exptl_crystal_recrystallization_method
'The material was recrystallised from acetonitrile'
_exptl_crystal_size_max          0.771
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4003
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0338
_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^)+(0.0541P)^2^+0.5934P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1058
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3441
_reflns_number_total             4003
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0dt01492c2.cif
_cod_data_source_block           2018ncs0910r1
_cod_depositor_comments
'Adding full bibliography for 7704441--7704445.cif.'
_cod_database_code               7704442
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H12 F20 N4 O4 '
_chemical_oxdiff_usercomment     MF054_CN
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.868
_reflns_odcompleteness_completeness 95.04
_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 N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C12(H12), C13(H13), C15(H15)
;
_shelx_res_checksum              91329
_olex2_date_sample_data_collection 2018-12-21
_olex2_date_sample_submission    2018-11-19
_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 MF054-CN
_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 2.264
_oxdiff_exptl_absorpt_empirical_full_min 0.311