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

data_7240170
_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, C2 H3 N, 3(Br)'
_chemical_formula_sum            'C44 H60 Br6 N4 O3'
_chemical_formula_weight         1172.36
_space_group_crystal_system      trigonal
_space_group_IT_number           147
_space_group_name_Hall           '-P 3'
_space_group_name_H-M_alt        'P -3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-13
_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                 90
_cell_angle_gamma                120
_cell_formula_units_Z            2
_cell_length_a                   16.57730(10)
_cell_length_b                   16.57730(10)
_cell_length_c                   10.49130(10)
_cell_measurement_reflns_used    17486
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.6810
_cell_measurement_theta_min      4.1920
_cell_volume                     2496.82(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.36a (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_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 1.000
_diffrn_measured_fraction_theta_max 0.998
_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      9.00  49.00   1.00    3.00    --   36.95  19.00  60.00   40
  2  \w    -30.00  35.00   1.00    3.00    --   36.95 -38.00 -90.00   65
  3  \w    -32.00  31.00   1.00    3.00    --   36.95 -19.00-150.00   63
  4  \w     30.00  76.00   1.00    3.00    --   36.95 -99.00-120.00   46
  5  \w      9.00  36.00   1.00    3.00    --   36.95 -99.00 120.00   27
  6  \w     22.00  51.00   1.00    3.00    --   36.95 -57.00   0.00   29
  7  \w    -21.00  18.00   1.00    3.00    --   36.95 -77.00 -90.00   39
  8  \w     -6.00  19.00   1.00    3.00    --   36.95 -57.00   0.00   25
  9  \w     29.00  64.00   1.00    3.00    --   36.95  57.00 120.00   35
 10  \w     21.00  47.00   1.00    3.00    --   36.95  57.00   0.00   26
 11  \w     32.00  96.00   1.00    3.00    --   36.95  38.00-120.00   64
 12  \w     54.00  80.00   1.00    3.00    --   36.95-125.00-180.00   26
 13  \w     57.00  85.00   1.00    3.00    --   36.95  19.00  60.00   28
 14  \w    -26.00  45.00   1.00    3.00    --   36.95 -57.00 120.00   71
 15  \w    -18.00  64.00   1.00    3.00    --   36.95 -77.00   0.00   82
 16  \w     42.00  88.00   1.00    3.00    --   36.95-125.00  90.00   46
 17  \w     44.00  73.00   1.00   15.00    --  111.00 -50.00-150.00   29
 18  \w    129.00 172.00   1.00   15.00    --  111.00  25.00 -90.00   43
 19  \w     42.00 135.00   1.00   15.00    --  111.00 -25.00-180.00   93
 20  \w     74.00 121.00   1.00   15.00    --  111.00 -50.00 -90.00   47
 21  \w     95.00 128.00   1.00   15.00    --  111.00  50.00 120.00   33
 22  \w     42.00 109.00   1.00   15.00    --  111.00-111.00-150.00   67
 23  \w     67.00  93.00   1.00   15.00    --  111.00 -38.00  90.00   26
 24  \w    145.00 170.00   1.00   15.00    --  111.00  38.00  90.00   25
 25  \w     62.00  90.00   1.00   15.00    --  111.00-172.00 118.00   28
 26  \w    101.00 137.00   1.00   15.00    --  111.00-172.00 118.00   36
 27  \w     43.00  91.00   1.00   15.00    --  111.00 -92.00  60.00   48
 28  \w     44.00 137.00   1.00   15.00    --  111.00 -77.00-150.00   93
 29  \w     97.00 134.00   1.00   15.00    --  111.00 -72.00 -13.23   37
 30  \w     56.00  97.00   1.00   15.00    --  111.00-111.00 -60.00   41
 31  \w     98.00 170.00   1.00   15.00    --  111.00  12.00 150.00   72
 32  \w     75.00 109.00   1.00   15.00    --  111.00-111.00  90.00   34
 33  \w    132.00 161.00   1.00   15.00    --  111.00 111.00  60.00   29
 34  \w     70.00 122.00   1.00   15.00    --  111.00 -64.00  30.00   52
 35  \w     44.00  91.00   1.00   15.00    --  111.00 -50.00  90.00   47
 36  \w    151.00 178.00   1.00   15.00    --  111.00  38.00   0.00   27
 37  \w     87.00 157.00   1.00   15.00    --  111.00 -12.00 -90.00   70
 38  \w     43.00  69.00   1.00   15.00    --  111.00 -12.00 -90.00   26
 39  \w     63.00 109.00   1.00   15.00    --  111.00-111.00 150.00   46
 40  \w     85.00 110.00   1.00   15.00    --  111.00-115.00-100.00   25
 41  \w     42.00  67.00   1.00   15.00    --  111.00-115.00-100.00   25
 42  \w     58.00  84.00   1.00   15.00    --  111.00 -92.00-150.00   26
 43  \w     92.00 125.00   1.00   15.00    --  111.00  38.00   0.00   33
 44  \w    150.00 176.00   1.00   15.00    --  111.00  50.00 150.00   26
 45  \w    102.00 128.00   1.00   15.00    --  111.00  50.00 150.00   26
 46  \w     95.00 124.00   1.00   15.00    --  111.00  50.00-150.00   29
 47  \w     84.00 109.00   1.00   15.00    --  111.00-111.00  60.00   25
 48  \w     96.00 134.00   1.00   15.00    --  111.00  38.00  90.00   38
 49  \w     62.00 120.00   1.00   15.00    --  111.00 178.00-180.00   58
 50  \w     68.00 125.00   1.00   15.00    --  111.00 -38.00-120.00   57
 51  \w     58.00  94.00   1.00   15.00    --  111.00 -92.00 -90.00   36
 52  \w     84.00 109.00   1.00   15.00    --  111.00-111.00 -30.00   25
 53  \w     53.00 144.00   1.00   15.00    --  111.00 -12.00  90.00   91
 54  \w     69.00  95.00   1.00   15.00    --  111.00 -64.00 -60.00   26
 55  \w     75.00 100.00   1.00   15.00    --  111.00 -77.00   0.00   25
 56  \w     75.00 104.00   1.00   15.00    --  111.00 -92.00 -30.00   29
 57  \w     84.00 109.00   1.00   15.00    --  111.00-111.00 120.00   25
 58  \w    115.00 141.00   1.00   15.00    --  111.00  77.00 120.00   26
 59  \w     58.00  83.00   1.00   15.00    --  111.00 -64.00 150.00   25
 60  \w     41.00  67.00   1.00   15.00    --  111.00-111.00  60.00   26
 61  \w     96.00 122.00   1.00   15.00    --  111.00 -64.00-150.00   26
 62  \w     72.00  97.00   1.00   15.00    --  111.00 -64.00  90.00   25
 63  \w     77.00 102.00   1.00   15.00    --  111.00 -92.00 150.00   25
 64  \w     58.00  97.00   1.00   15.00    --  111.00 -32.00 -17.98   39
 65  \w     78.00 103.00   1.00   15.00    --  111.00 -80.00 -98.55   25
;
_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      0.0365277000
_diffrn_orient_matrix_UB_12      -0.0608125000
_diffrn_orient_matrix_UB_13      0.0588503000
_diffrn_orient_matrix_UB_21      0.0976813000
_diffrn_orient_matrix_UB_22      0.0864755000
_diffrn_orient_matrix_UB_23      0.0125946000
_diffrn_orient_matrix_UB_31      -0.0252307000
_diffrn_orient_matrix_UB_32      0.0185688000
_diffrn_orient_matrix_UB_33      0.1339105000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            31656
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.695
_diffrn_reflns_theta_min         4.214
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.36a (Rigaku Oxford Diffraction, 2018)
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    1.559
_exptl_crystal_description       needle
_exptl_crystal_F_000             1172
_exptl_crystal_recrystallization_method
'diffusion of diethyl into acetonirtile'
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.021
_refine_diff_density_min         -0.867
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3363
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.192
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1390
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3110
_reflns_number_total             3363
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce00241k2.cif
_cod_data_source_block           emf-4-58g
_cod_original_cell_volume        2496.82(4)
_cod_database_code               7240170
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C42H57N3O3Br6
_shelx_estimated_absorpt_t_max   0.580
_shelx_estimated_absorpt_t_min   0.169
_reflns_odcompleteness_completeness 98.05
_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. Others
 Fixed Sof: H16A(0.33333) H16B(0.33333) H16C(0.33333)
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B),
 C12(H12A,H12B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C3(H3), C2(H2)
3.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              6533
_ins_header
;
TITL EMF-4-58g in P-3 
REM P-3 (#147 in standard setting)
CELL 1.54184  16.577268  16.577268  10.491264  90.0000  90.0000 120.0000
ZERR    3.00   0.000148   0.000148   0.000085   0.0000   0.0000   0.0000
LATT  1
SYMM -y, x-y, z 
SYMM -x+y,-x, z 
SFAC C H N O Br
UNIT 126.00 171.00 9.00 9.00 18.00
TREF
HKLF 4
END
;
_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 3.190
_oxdiff_exptl_absorpt_empirical_full_min 0.455