Highly selective anion template effect in the synthesis of constrained pseudopeptidic macrocyclic cyclophanes.
Esteve, Ferran; Altava, Belen; Bolte, Michael; Burguete, Maria Isabel; Garcia-Verdugo, Eduardo; Luis, Santiago V.; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b03048

data_4037760
_publ_section_title
;
 Highly selective anion template effect in the synthesis of constrained
 pseudopeptidic macrocyclic cyclophanes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03048
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H32 N4 O2'
_chemical_formula_sum            'C22 H32 N4 O2'
_chemical_formula_weight         384.51
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5748(2)
_cell_length_b                   14.0946(3)
_cell_length_c                   15.6037(3)
_cell_measurement_reflns_used    10365
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      73.271
_cell_measurement_theta_min      4.167
_cell_volume                     2105.77(7)
_computing_cell_refinement       CrysAlisPro
_computing_data_collection       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 10.4051
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  SuperNova
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19919
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         73.372
_diffrn_reflns_theta_min         4.227
_diffrn_source                   micro-focus
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.5241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       Fiber
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.752
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1634 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(8)
_refine_ls_extinction_coef       0.0041(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4187
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0473
_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^)+(0.0469P)^2^+0.8603P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1179
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                3984
_reflns_number_total             4187
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03048_si_002.cif
_cod_data_source_block           3a
_cod_database_code               4037760
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.650
_shelx_estimated_absorpt_t_max   0.952
_shelx_res_checksum              38882
_shelx_hkl_checksum              63183