Anion templated crystal engineering of halogen bonding tripodal tris(halopyridinium) compounds
Foyle, Émer M.; White, Nicholas G.; CrystEngComm  (2020) –; doi:10.1039/D0CE00241K

data_7240168
_publ_section_title
;
 Anion templated crystal engineering of halogen bonding tripodal
 tris(halopyridinium) compounds
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00241K
_journal_year                    2020
_chemical_formula_moiety         'C42 H57 Br3 N3 O3, 3(F6 P)'
_chemical_formula_sum            'C42 H57 Br3 F18 N3 O3 P3'
_chemical_formula_weight         1326.54
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-01-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-18 deposited with the CCDC.	2020-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.6230(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.50630(10)
_cell_length_b                   25.6914(4)
_cell_length_c                   24.6665(3)
_cell_measurement_reflns_used    15448
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.7010
_cell_measurement_theta_min      4.9880
_cell_volume                     5354.61(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_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     23.00  90.00   1.00    2.50    --   36.95-125.00-120.00   67
  2  \w     45.00  90.00   1.00    2.50    --   36.95-125.00 150.00   45
  3  \w    -15.00  16.00   1.00    2.50    --   36.95 -19.00-150.00   31
  4  \w     20.00  87.00   1.00    2.50    --   36.95  38.00  90.00   67
  5  \w     24.00 103.00   1.00    2.50    --   36.95  57.00 150.00   79
  6  \w     65.00  97.00   1.00    2.50    --   36.95  57.00-180.00   32
  7  \w     20.00  67.00   1.00    2.50    --   36.95 -99.00   0.00   47
  8  \w     34.00  59.00   1.00    2.50    --   36.95 -19.00-150.00   25
  9  \w     20.00  45.00   1.00    2.50    --   36.95  19.00 120.00   25
 10  \w     24.00  66.00   1.00    2.50    --   36.95 -99.00 -30.00   42
 11  \w     45.00  99.00   1.00    8.00    --  111.00 -77.00 120.00   54
 12  \w     83.00 119.00   1.00    8.00    --  111.00 -50.00 -90.00   36
 13  \w     77.00 107.00   1.00    8.00    --  111.00 -92.00-120.00   30
 14  \w    105.00 132.00   1.00    8.00    --  111.00 -77.00 120.00   27
 15  \w     46.00  71.00   1.00    8.00    --  111.00 -50.00 -90.00   25
 16  \w    122.00 178.00   1.00    8.00    --  111.00 111.00-150.00   56
 17  \w    121.00 172.00   1.00    8.00    --  111.00  77.00 -90.00   51
 18  \w    103.00 129.00   1.00    8.00    --  111.00 -77.00-120.00   26
 19  \w     43.00  69.00   1.00    8.00    --  111.00 -77.00-120.00   26
 20  \w    144.00 170.00   1.00    8.00    --  111.00 111.00  60.00   26
 21  \w     58.00 115.00   1.00    8.00    --  111.00 -50.00  90.00   57
 22  \w     97.00 123.00   1.00    8.00    --  111.00  38.00-180.00   26
 23  \w     59.00 138.00   1.00    8.00    --  111.00 178.00 150.00   79
 24  \w    121.00 146.00   1.00    8.00    --  111.00  38.00 -30.00   25
 25  \w    140.00 170.00   1.00    8.00    --  111.00  64.00   0.00   30
 26  \w     42.00  68.00   1.00    8.00    --  111.00 -92.00-120.00   26
 27  \w     86.00 113.00   1.00    8.00    --  111.00-111.00   0.00   27
 28  \w    135.00 160.00   1.00    8.00    --  111.00  38.00 -60.00   25
 29  \w     72.00 112.00   1.00    8.00    --  111.00-111.00-150.00   40
 30  \w     42.00  80.00   1.00    8.00    --  111.00 -25.00-120.00   38
 31  \w    142.00 168.00   1.00    8.00    --  111.00 111.00 -30.00   26
 32  \w     48.00  73.00   1.00    8.00    --  111.00-111.00   0.00   25
 33  \w    107.00 133.00   1.00    8.00    --  111.00 -25.00-120.00   26
 34  \w    102.00 128.00   1.00    8.00    --  111.00  12.00-180.00   26
 35  \w    139.00 164.00   1.00    8.00    --  111.00  12.00-180.00   25
 36  \w    104.00 138.00   1.00    8.00    --  111.00 111.00 -30.00   34
 37  \w     94.00 120.00   1.00    8.00    --  111.00  64.00   0.00   26
 38  \w     59.00 109.00   1.00    8.00    --  111.00 -92.00 -90.00   50
 39  \w     89.00 115.00   1.00    8.00    --  111.00  77.00 -90.00   26
 40  \w     96.00 125.00   1.00    8.00    --  111.00 -73.00-136.98   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0074461000
_diffrn_orient_matrix_UB_12      0.0250322000
_diffrn_orient_matrix_UB_13      0.0564263000
_diffrn_orient_matrix_UB_21      -0.0830539000
_diffrn_orient_matrix_UB_22      -0.0489492000
_diffrn_orient_matrix_UB_23      0.0188420000
_diffrn_orient_matrix_UB_31      0.1620916000
_diffrn_orient_matrix_UB_32      -0.0239399000
_diffrn_orient_matrix_UB_33      0.0203966000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            36746
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.834
_diffrn_reflns_theta_min         3.885
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.575
_exptl_absorpt_correction_T_max  0.583
_exptl_absorpt_correction_T_min  0.278
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (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    1.646
_exptl_crystal_description       needle
_exptl_crystal_F_000             2664
_exptl_crystal_recrystallization_method
'Slow evaporation of MeOH/EtOH of the receptor with 1.5 equivalents of TBA.Cl.'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.674
_refine_diff_density_min         -1.059
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     717
_refine_ls_number_reflns         10758
_refine_ls_number_restraints     96
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0971
_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^)+(0.1514P)^2^+15.5694P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2696
_refine_ls_wR_factor_ref         0.2784
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9262
_reflns_number_total             10758
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce00241k2.cif
_cod_data_source_block           emf2-34b
_cod_database_code               7240168
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H20 N3 Br3 O3 Cl2'
_reflns_odcompleteness_completeness 98.10
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. 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
2. Restrained distances
 C36-C37
 1.53 with sigma of 0.02
 C37-C38
 1.53 with sigma of 0.02
 C38-C39
 1.53 with sigma of 0.02
 C39-C40
 1.53 with sigma of 0.02
 C40-C41
 1.53 with sigma of 0.02
 C36-C38
 2.55 with sigma of 0.02
 C37-C39
 2.55 with sigma of 0.02
 C38-C40
 2.55 with sigma of 0.02
 C39-C41
 2.55 with sigma of 0.02
 C23-C24
 1.53 with sigma of 0.01
 C24-C25
 1.53 with sigma of 0.01
 C25-C26
 1.53 with sigma of 0.01
 C26-C27
 1.53 with sigma of 0.01
 C27-C28
 1.53 with sigma of 0.01
 C23-C25
 2.55 with sigma of 0.02
 C24-C26
 2.55 with sigma of 0.02
 C25-C27
 2.55 with sigma of 0.02
 C26-C28
 2.55 with sigma of 0.02
3. Rigid bond restraints
 C36, C37, C38, C39, C40, C41
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C23, C24, C25, C26, C27, C28
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
C36 \\sim C37 \\sim C38 \\sim C39 \\sim C40 \\sim C41: within 1.7A with sigma
of 0.02 and sigma for terminal atoms of 0.04
C23 \\sim C24 \\sim C25 \\sim C26 \\sim C27 \\sim C28: within 1.7A with sigma
of 0.02 and sigma for terminal atoms of 0.04
5. Others
 Sof(Br3)=Sof(H18)=1-FVAR(1)
 Sof(Br4)=Sof(H20)=FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F7)=1-FVAR(2)
 Sof(F1A)=Sof(F5A)=Sof(F2A)=Sof(F4A)=Sof(F6A)=Sof(F3A)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C36(H36A,H36B), C40(H40A,H40B), C39(H39A,H39B), C38(H38A,H38B), C37(H37A,
 H37B), C6(H6A,H6B), C13(H13A,H13B), C12(H12A,H12B), C11(H11A,H11B), C10(H10A,
 H10B), C9(H9A,H9B), C16(H16A,H16B), C27(H27A,H27B), C26(H26A,H26B), C25(H25A,
 H25B), C24(H24A,H24B), C23(H23A,H23B), C29(H29A,H29B)
6.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C3(H3), C1(H1), C21(H21), C20(H20), C19(H19), C18(H18),
 C17(H17), C30(H30), C32(H32), C33(H33), C34(H34)
6.c Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C), C14(H14A,H14B,H14C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              95508
_olex2_date_sample_data_collection 2018-09-04
_olex2_submission_original_sample_id EMF-2-34B
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.298
_oxdiff_exptl_absorpt_empirical_full_min 0.530