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_4037762
_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 syn
_chemical_formula_moiety         'C23 H34 N4 O2'
_chemical_formula_sum            'C23 H34 N4 O2'
_chemical_formula_weight         398.54
_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
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9079(3)
_cell_length_b                   14.3041(5)
_cell_length_c                   16.0300(6)
_cell_measurement_reflns_used    5926
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.492
_cell_measurement_theta_min      4.08
_cell_volume                     2271.83(14)
_computing_cell_refinement       CrysAlisPro
_computing_data_collection       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4051
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0340
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20119
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.593
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_min         4.142
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.612
_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_density_diffrn    1.165
_exptl_crystal_description       Fiber
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1217 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.15(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         4007
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0553
_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^)+(0.1013P)^2^+0.3769P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1537
_refine_ls_wR_factor_ref         0.1674
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3269
_reflns_number_total             4007
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03048_si_003.cif
_cod_data_source_block           str2059_a
_cod_database_code               4037762
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.826
_shelx_estimated_absorpt_t_max   0.962
_shelx_res_checksum              85361
_shelx_hkl_checksum              77221