C–H functionalization enabled stereoselective Ugi-azide reaction to α-tetrazolyl alicyclic amines
Haldar, Surajit; Saha, Subhajit; Mandal, Sumana; Jana, Chandan K.; Green Chemistry 20 (2018) 3463–; doi:10.1039/C8GC01544A

data_7231097
_publ_section_title
;
 C--H functionalization enabled stereoselective Ugi-azide reaction to
 \a-tetrazolyl alicyclic amines
;
_journal_issue                   15
_journal_name_full               'Green Chemistry'
_journal_page_first              3463
_journal_paper_doi               10.1039/C8GC01544A
_journal_volume                  20
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_formula_sum            'C26 H24 Cl N5 O'
_chemical_formula_weight         457.95
_chemical_name_systematic
((2S,5R)-5-(1-(4-chlorobenzyl)-1H-tetrazol-5-yl)-1-(9H-fluoren-9-yl)pyrrolidin-2-yl)methanol
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-03-14 deposited with the CCDC.
2018-07-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.110(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5211(10)
_cell_length_b                   11.9295(7)
_cell_length_c                   20.9205(17)
_cell_measurement_reflns_used    892
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.6780
_cell_measurement_theta_min      3.4080
_cell_volume                     2339.3(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_sigmaI/netI    0.1605
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9851
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58274
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate and Hexane'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.14(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         6254
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.1806
_refine_ls_R_factor_gt           0.0723
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0050P)^2^+1.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.1282
_reflns_number_gt                2769
_reflns_number_total             6254
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8gc01544a3.cif
_cod_data_source_block           CKJ-SH-04-291D
_cod_depositor_comments
'Adding full bibliography for 7231095--7231101.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7231097