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_7704445
_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_absolute_configuration ad
_chemical_formula_moiety
'C19 H3 F10 N3 O2, 2(C16 H36 N), H2 O, 0.25[(OH2)], 0.5[(OH2)]'
_chemical_formula_sum            'C51 H78.5 F10 N5 O3.75'
_chemical_formula_weight         1011.68
_space_group_crystal_system      trigonal
_space_group_IT_number           159
_space_group_name_Hall           'P 3 -2c'
_space_group_name_H-M_alt        'P 3 1 c'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-04-21 deposited with the CCDC.	2020-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   40.29774(8)
_cell_length_b                   40.29774(8)
_cell_length_c                   17.08786(4)
_cell_measurement_reflns_used    250068
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.1690
_cell_measurement_theta_min      2.8400
_cell_volume                     24031.43(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_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_environment      N~2~
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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     14.00  94.00   0.50    0.70    --    5.00  59.00  90.00  160
  2  \w    -13.00  38.00   0.50    0.70    --    5.00   5.00-116.00  102
  3  \w    -83.00 -58.00   0.50    0.70    --    5.00  59.00  90.00   50
  4  \w    -77.00 -52.00   0.50    0.70    --  -52.30   5.00-116.00   50
  5  \w     -3.00  37.00   0.50    0.70    --  -52.30  59.00  90.00   80
  6  \w   -133.00-107.00   0.50    0.70    --  -52.30  49.00 150.00   52
  7  \w    -11.00  36.00   0.50    0.70    --  -52.30  49.00-180.00   94
  8  \w    -34.00  37.00   0.50    0.70    --  -52.30  59.00 150.00  142
  9  \w   -142.00-112.00   0.50    0.70    --  -52.30  59.00 150.00   60
 10  \w     11.00  37.00   0.50    0.70    --  -52.30  49.00 150.00   52
 11  \w   -124.00 -80.00   0.50    1.00    --  -90.00   5.00-116.00   88
 12  \w   -173.00-146.00   0.50    1.00    --  -90.00   5.00-116.00   54
 13  \w   -121.00 -37.00   0.50    1.00    --  -90.00  56.00 105.63  168
 14  \w   -167.00-142.00   0.50    1.00    --  -90.00  58.00-161.36   50
 15  \w    -27.00  -1.00   0.50    1.00    --  -90.00  59.00-177.76   52
 16  \w    -31.00  -1.00   0.50    1.00    --  -90.00  56.00 105.63   60
 17  \w    -50.00  -1.00   0.50    1.00    --  -90.00  58.00 151.15   98
 18  \w    -28.00  -1.00   0.50    1.00    --  -90.00  59.00 165.54   54
 19  \w   -123.00 -97.00   0.50    1.00    --  -90.00  59.00 119.86   52
 20  \w    -98.00 -55.00   0.50    1.00    --  -90.00  59.00 165.54   86
 21  \w    -85.00 -59.00   0.50    1.00    --  -90.00  59.00 145.85   52
 22  \w    -27.00  -1.00   0.50    1.00    --  -90.00  59.00 127.14   52
 23  \w   -142.00  -2.00   0.50    1.00    --  -90.00  59.00 178.62  280
 24  \w    -27.00  -1.00   0.50    1.00    --  -90.00  59.00 145.85   52
 25  \w    -90.00 -32.00   0.50    1.00    --  -90.00  59.00 127.14  116
 26  \w   -179.00-131.00   0.50    1.00    --  -90.00  59.00  40.35   96
 27  \w   -153.00  -2.00   0.50    1.00    --  -90.00  58.00 136.24  302
 28  \w    -26.00  -1.00   0.50    1.00    --  -90.00  59.00-169.42   50
 29  \w    -27.00  -1.00   0.50    1.00    --  -90.00  58.00-161.36   52
 30  \w    -35.00  -1.00   0.50    1.00    --  -90.00  59.00 105.97   68
 31  \w   -135.00  -3.00   0.50    1.00    --  -90.00  57.00 157.73  264
 32  \w    -29.00  -3.00   0.50    1.00    --  -90.00  59.00 133.49   52
 33  \w   -147.00  -1.00   0.50    1.00    --  -90.00  57.00-165.93  292
 34  \w    -89.00 -50.00   0.50    1.00    --  -90.00  59.00-169.42   78
 35  \w   -179.00 -34.00   0.50    1.00    --  -90.00  59.00  93.58  290
 36  \w    -26.00  -1.00   0.50    1.00    --  -90.00  59.00 121.81   50
 37  \w    -27.00  -2.00   0.50    1.00    --  -90.00  57.00 166.76   50
 38  \w    -70.00  -1.00   0.50    1.00    --  -90.00  59.00 119.86  138
 39  \w   -165.00-128.00   0.50    1.00    --  -90.00  59.00 119.86   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC11 quarter \c goniometer'
_diffrn_measurement_device_type
'Rigaku 007HF equipped with Varimax confocal mirrors and an AFC11 goniometer and HyPix 6000 detector'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen loops'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0368378000
_diffrn_orient_matrix_UB_12      -0.0024441000
_diffrn_orient_matrix_UB_13      -0.0070775000
_diffrn_orient_matrix_UB_21      -0.0240162000
_diffrn_orient_matrix_UB_22      -0.0440474000
_diffrn_orient_matrix_UB_23      0.0037625000
_diffrn_orient_matrix_UB_31      -0.0039286000
_diffrn_orient_matrix_UB_32      -0.0016736000
_diffrn_orient_matrix_UB_33      -0.0897749000
_diffrn_radiation_collimation    'Varimax focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            396162
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.245
_diffrn_reflns_theta_min         2.532
_diffrn_source                   'Rotating anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rigaku 007 HF'
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    0.870
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.788
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
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    1.258
_exptl_crystal_description       'cut block'
_exptl_crystal_F_000             9711
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of DCM and diethyl ether  by solvent layering'
_exptl_crystal_size_max          0.368
_exptl_crystal_size_mid          0.219
_exptl_crystal_size_min          0.175
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.50(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2013
_refine_ls_number_reflns         28906
_refine_ls_number_restraints     190
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0285
_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^+2.9405P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0801
_reflns_Friedel_coverage         0.975
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                28518
_reflns_number_total             28906
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0dt01492c2.cif
_cod_data_source_block           2019ncs0117
_cod_depositor_comments
'Adding full bibliography for 7704441--7704445.cif.'
_cod_original_cell_volume        24031.42(11)
_cod_original_formula_sum        'C51 H78.50 F10 N5 O3.75'
_cod_database_code               7704445
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C51 H78.5 F10 N5 O3.75'
_chemical_oxdiff_usercomment     MF058_F
_shelx_estimated_absorpt_t_max   0.863
_shelx_estimated_absorpt_t_min   0.740
_reflns_odcompleteness_completeness 99.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.50(5)
 0.50(5)
2. 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, All O(H,H) groups
3. Rigid body (RIGU) restrains
 C27A, C28A, C29A, C30A, C31A, C32A, F21A, F22A, F24A, F25A
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C23, C27A, C27B, C28B, C29B, C30B, C31B, C32B, F21A, F21B, F22A, F22B, F23A,
 F23B, F24A, F24B, F25A, F25B, N5A, N5B, O3A, O3B
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
4. Others
 Sof(C27B)=Sof(C28B)=Sof(C29B)=Sof(C30B)=Sof(C31B)=Sof(C32B)=Sof(F21B)=
 Sof(F22B)=Sof(F23B)=Sof(F24B)=Sof(F25B)=Sof(N5B)=Sof(O3B)=1-FVAR(1)
 Sof(C27A)=Sof(C28A)=Sof(C29A)=Sof(C30A)=Sof(C31A)=Sof(C32A)=Sof(F21A)=
 Sof(F22A)=Sof(F23A)=Sof(F24A)=Sof(F25A)=Sof(N5A)=Sof(O3A)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C58(H58A,H58B), C59(H59A,H59B), C60(H60A,H60B), C62(H62A,H62B), C63(H63A,
 H63B), C64(H64A,H64B), C66(H66A,H66B), C67(H67A,H67B), C68(H68A,H68B),
 C70(H70A,H70B), C71(H71A,H71B), C72(H72A,H72B), C74(H74A,H74B), C75(H75A,H75B),
  C76(H76A,H76B), C78(H78A,H78B), C79(H79A,H79B), C80(H80A,H80B), C82(H82A,
 H82B), C83(H83A,H83B), C84(H84A,H84B), C86(H86A,H86B), C87(H87A,H87B),
 C88(H88A,H88B), C90(H90A,H90B), C91(H91A,H91B), C92(H92A,H92B), C94(H94A,H94B),
  C95(H95A,H95B), C96(H96A,H96B), C98(H98A,H98B), C99(H99A,H99B), C100(H10A,
 H10B), C102(H10F,H10G), C103(H10H,H10I), C104(H10J,H10K), C106(H10O,H10P),
 C107(H10Q,H10R), C108(H10S,H10T), C110(H11A,H11B), C111(H11C,H11D), C112(H11E,
 H11F), C114(H11J,H11K), C115(H11L,H11M), C116(H11N,H11O), C118(H11S,H11T),
 C119(H11U,H11V), C120(H12A,H12B), C122(H12F,H12G), C123(H12H,H12I), C124(H12J,
 H12K), C126(H12O,H12P), C127(H12Q,H12R), C128(H12S,H12T), C130(H13A,H13B),
 C131(H13C,H13D), C132(H13E,H13F), C134(H13J,H13K), C135(H13L,H13M), C136(H13N,
 H13O), C138(H13S,H13T), C139(H13U,H13V), C140(H14A,H14B), C142(H14F,H14G),
 C143(H14H,H14I), C144(H14J,H14K), C146(H14O,H14P), C147(H14Q,H14R), C148(H14S,
 H14T), C150(H15A,H15B), C151(H15C,H15D), C152(H15E,H15F)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C20(H20), C21(H21), C24(H24), C39(H39), C40(H40),
 C43(H43)
5.c Fitted hexagon refined as free rotating group:
 C27B(C28B,C29B,C30B,C31B,C32B)
5.d Idealised Me refined as rotating group:
 C61(H61A,H61B,H61C), C65(H65A,H65B,H65C), C69(H69A,H69B,H69C), C73(H73A,H73B,
 H73C), C77(H77A,H77B,H77C), C81(H81A,H81B,H81C), C85(H85A,H85B,H85C), C89(H89A,
 H89B,H89C), C93(H93A,H93B,H93C), C97(H97A,H97B,H97C), C101(H10C,H10D,H10E),
 C105(H10L,H10M,H10N), C109(H10U,H10V,H10W), C113(H11G,H11H,H11I), C117(H11P,
 H11Q,H11R), C121(H12C,H12D,H12E), C125(H12L,H12M,H12N), C129(H12U,H12V,H12W),
 C133(H13G,H13H,H13I), C137(H13P,H13Q,H13R), C141(H14C,H14D,H14E), C145(H14L,
 H14M,H14N), C149(H14U,H14V,H14W), C153(H15G,H15H,H15I)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 42 electrons were found in a volume of 1092\%A^3 in 2 voids per unit cell.
This is consistent with the presence of 0.25[H2O] and 0.75[H2O] per Asymmetric Unit which account for 40 electrons per unit cell.
;
_smtbx_masks_void_probe_radius   1.24
_smtbx_masks_void_truncation_radius 1.1
_shelx_res_checksum              19334
_shelx_fab_checksum              10457
_olex2_date_sample_data_collection 2019-04-13
_olex2_date_sample_submission    2019-02-15
_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 MF058_F
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.753
_oxdiff_exptl_absorpt_empirical_full_min 0.714