Azacalixquinarenes: From Canonical to (Poly-)Zwitterionic Macrocycles.
Pascal, Simon; Lavaud, Lucien; Azarias, Cloé; Varlot, Alexandre; Canard, Gabriel; Giorgi, Michel; Jacquemin, Denis; Siri, Olivier; The Journal of organic chemistry 84 (2019) 1387–1397; doi:10.1021/acs.joc.8b02847

data_4037563
_publ_section_title
;
 Azacalixquinarenes: From Canonical to (Poly-)Zwitterionic Macrocycles.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1387
_journal_page_last               1397
_journal_paper_doi               10.1021/acs.joc.8b02847
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C36 H30 F2 N8 O14'
_chemical_formula_sum            'C36 H30 F2 N8 O14'
_chemical_formula_weight         836.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.086(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5522(7)
_cell_length_b                   13.2766(6)
_cell_length_c                   11.9930(5)
_cell_measurement_reflns_used    4766
_cell_measurement_temperature    203.01(10)
_cell_measurement_theta_max      67.7450
_cell_measurement_theta_min      3.7480
_cell_volume                     1810.99(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_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      203.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_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     44.00 101.00   1.00    1.00    --    0.00  57.00-150.00   57
  2  \w    -37.00  37.00   1.00    1.00    --    0.00  57.00-150.00   74
  3  \w   -103.00 -55.00   1.00    1.00    --    0.00 178.00 -90.00   48
  4  \w   -155.00-122.00   1.00    5.00    --  -53.65 -94.00   0.00   33
  5  \w    -23.00  41.00   1.00    5.00    --  -53.65  61.00 -60.00   64
  6  \w   -149.00 -78.00   1.00    5.00    --  -53.65-125.00 120.00   71
  7  \w   -155.00 -88.00   1.00    5.00    --  -53.65 -94.00  60.00   67
  8  \w   -150.00  -6.00   1.00    5.00    --  -53.65 -77.00 -60.00  144
  9  \w     36.00  63.00   1.00    5.00    --   53.65 -61.00 150.00   27
 10  \w    -41.00  13.00   1.00    5.00    --   53.65 -61.00 150.00   54
 11  \w     26.00 121.00   1.00    5.00    --   53.65-125.00   0.00   95
 12  \w     15.00  41.00   1.00    5.00    --   53.65 -94.00   0.00   26
 13  \w     79.00 104.00   1.00    5.00    --   53.65 -94.00   0.00   25
 14  \w    103.00 171.00   1.00   30.00    --  107.30  38.00 -90.00   68
 15  \w     96.00 123.00   1.00   30.00    --  107.30  77.00 -60.00   27
 16  \w     55.00  87.00   1.00   30.00    --  107.30  38.00 -90.00   32
 17  \w     61.00 142.00   1.00   30.00    --  107.30  77.00-180.00   81
 18  \w     32.00 114.00   1.00   30.00    --  107.30-111.00  60.00   82
 19  \w     59.00 143.00   1.00   30.00    --  107.30  63.00 -60.00   84
 20  \w    127.00 154.00   1.00   30.00    --  107.30 111.00 120.00   27
 21  \w    123.00 178.00   1.00   30.00    --  107.30 111.00 -90.00   55
 22  \w     82.00 107.00   1.00   30.00    --  107.30-111.00-120.00   25
 23  \w     20.00  71.00   1.00   30.00    --  107.30-111.00-120.00   51
 24  \w    100.00 164.00   1.00   30.00    --  107.30 111.00-180.00   64
 25  \w    103.00 171.00   1.00   30.00    --  107.30 111.00-150.00   68
 26  \w    101.00 167.00   1.00   30.00    --  107.30 111.00 -60.00   66
 27  \w    114.00 175.00   1.00   30.00    --  107.30 111.00-120.00   61
 28  \w     60.00 161.00   1.00   30.00    --  107.30  50.00   0.00  101
 29  \w     57.00 151.00   1.00   30.00    --  107.30 178.00  60.00   94
 30  \w     85.00 121.00   1.00   30.00    --  107.30  75.00-133.00   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0348115000
_diffrn_orient_matrix_UB_12      -0.0912323000
_diffrn_orient_matrix_UB_13      0.0663447000
_diffrn_orient_matrix_UB_21      -0.1307137000
_diffrn_orient_matrix_UB_22      0.0279403000
_diffrn_orient_matrix_UB_23      -0.0354126000
_diffrn_orient_matrix_UB_31      -0.0074994000
_diffrn_orient_matrix_UB_32      -0.0659627000
_diffrn_orient_matrix_UB_33      -0.1066760000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0649
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11143
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.967
_diffrn_reflns_theta_min         3.743
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.18b (Rigaku Oxford Diffraction, 2015)
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    1.534
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.6(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     548
_refine_ls_number_reflns         6467
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0523
_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^)+(0.0812P)^2^+0.0061P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1430
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                5670
_reflns_number_total             6467
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02847_si_001.cif
_cod_data_source_block           sp109mecn
_cod_database_code               4037563
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'c36 h30 f2 n8 o14'
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.735
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.4(3)
 0.6(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C2(H2), C5(H5), C9(H9), C12(H12), C15(H15), C18(H18),
 C20(H20), C24(H24), C29(H29), C33(H33)
3.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C34(H34A,H34B,
 H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C)
;
_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 2.018
_oxdiff_exptl_absorpt_empirical_full_min 0.529