Supramolecular chirality and symmetry breaking of fluoride complexes of achiral foldamers
Helttunen, Kaisa; Annala, Riia; Suhonen, Aku; Nauha, Elisa; Linnanto, Juha; Nissinen, Maija; CrystEngComm  (2017) –; doi:10.1039/C7CE01109A

data_7228922
_publ_section_title
;
 Supramolecular chirality and symmetry breaking of fluoride complexes of
 achiral foldamers
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE01109A
_journal_year                    2017
_chemical_formula_moiety         'C33 H25 N5 O4, C16 H36 N, F'
_chemical_formula_sum            'C49 H61 F N6 O4'
_chemical_formula_weight         817.03
_chemical_name_common
'N2,N6-bis(2-benzamidophenyl)pyridine-2,6-dicarboxamide tetra-butyl ammonium fluoride complex'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2017-08-04 deposited with the CCDC.
2017-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.16653(6)
_cell_length_b                   16.03601(10)
_cell_length_c                   24.54325(15)
_cell_measurement_reflns_used    23030
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      76.5980
_cell_measurement_theta_min      4.3190
_cell_volume                     4394.88(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_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    -57.00  33.00   1.00    7.50    --  -41.65  37.00-180.00   90
  2  \w     30.00  95.00   1.00    7.50    --   41.65-125.00 150.00   65
  3  \w     31.00  86.00   1.00    7.50    --   41.65-125.00  30.00   55
  4  \w     27.00  59.00   1.00    7.50    --   41.65-125.00 -30.00   32
  5  \w    130.00 156.00   1.00   35.00    --  112.00  77.00 -30.00   26
  6  \w     89.00 119.00   1.00   35.00    --  112.00  61.00 120.00   30
  7  \w     99.00 128.00   1.00   35.00    --  112.00 -77.00-180.00   29
  8  \w     54.00 127.00   1.00   35.00    --  112.00 -45.00-180.00   73
  9  \w     43.00  82.00   1.00   35.00    --  112.00 -77.00-180.00   39
 10  \w     79.00 107.00   1.00   35.00    --  112.00  77.00 -30.00   28
 11  \w     79.00 110.00   1.00   35.00    --  112.00-111.00  30.00   31
 12  \w     55.00  96.00   1.00   35.00    --  112.00 -61.00 -90.00   41
 13  \w    108.00 137.00   1.00   35.00    --  112.00 -61.00 -90.00   29
 14  \w    112.00 170.00   1.00   35.00    --  112.00  45.00 -90.00   58
 15  \w     41.00  67.00   1.00   35.00    --  112.00 -30.00-180.00   26
 16  \w    133.00 160.00   1.00   35.00    --  112.00  45.00-120.00   27
 17  \w     95.00 128.00   1.00   35.00    --  112.00  45.00-120.00   33
 18  \w     86.00 112.00   1.00   35.00    --  112.00 -30.00-180.00   26
 19  \w     43.00  80.00   1.00   35.00    --  112.00 -32.00 -30.44   37
 20  \w     82.00 130.00   1.00   35.00    --  112.00 -32.00 -30.44   48
 21  \w    104.00 142.00   1.00   35.00    --  112.00 111.00 -30.00   38
 22  \w     39.00  65.00   1.00   35.00    --  112.00-111.00  30.00   26
 23  \w    136.00 168.00   1.00   35.00    --  112.00  61.00 120.00   32
 24  \w     60.00 134.00   1.00   35.00    --  112.00 -45.00   0.00   74
 25  \w     59.00 178.00   1.00   35.00    --  112.00  15.00-150.00  119
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            30278
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.804
_diffrn_reflns_theta_min         3.602
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       block
_exptl_crystal_F_000             1752
_exptl_crystal_size_max          0.227
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 3952 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     557
_refine_ls_number_reflns         9228
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0320
_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^)+(0.0513P)^2^+0.7610P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0850
_reflns_Friedel_coverage         0.796
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                9005
_reflns_number_total             9228
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce01109a2.cif
_cod_data_source_block           1-TBAF
_cod_database_code               7228922
_shelx_estimated_absorpt_t_min   0.866
_shelx_estimated_absorpt_t_max   0.946
_shelxl_version_number           2014/6
_shelx_res_checksum              29383