A highly enantioselective synthetic method towards the α2c-adrenoceptor antagonist ORM-10921
Ma, Qiaoning; Yang, Xiaodi; Lei, Xinsheng; Lin, Guo-Qiang; Organic Chemistry Frontiers 6 (2019) 773–; doi:10.1039/C8QO01166D

data_1554526
_publ_section_title
;
 A highly enantioselective synthetic method towards the \a2c-adrenoceptor
 antagonist ORM-10921
;
_journal_issue                   6
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              773
_journal_paper_doi               10.1039/C8QO01166D
_journal_volume                  6
_journal_year                    2019
_chemical_formula_sum            'C21 H28 N2 O8'
_chemical_formula_weight         436.45
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-12-20 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.533(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.4833(6)
_cell_length_b                   7.3773(5)
_cell_length_c                   13.1160(7)
_cell_measurement_temperature    173(2)
_cell_volume                     1103.92(11)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.916
_diffrn_measured_fraction_theta_max 0.916
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.2527
_diffrn_reflns_av_unetI/netI     0.1527
_diffrn_reflns_Laue_measured_fraction_full 0.916
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5125
_diffrn_reflns_point_group_measured_fraction_full 0.706
_diffrn_reflns_point_group_measured_fraction_max 0.706
_diffrn_reflns_theta_full        67.492
_diffrn_reflns_theta_max         67.492
_diffrn_reflns_theta_min         3.874
_exptl_absorpt_coefficient_mu    0.849
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.777
_refine_diff_density_min         -0.849
_refine_diff_density_rms         0.203
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   1.7(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.408
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         2812
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.405
_refine_ls_R_factor_all          0.1605
_refine_ls_R_factor_gt           0.1491
_refine_ls_shift/su_max          0.156
_refine_ls_shift/su_mean         0.027
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3396
_refine_ls_wR_factor_ref         0.3552
_reflns_Friedel_coverage         0.422
_reflns_Friedel_fraction_full    0.457
_reflns_Friedel_fraction_max     0.457
_reflns_number_gt                2219
_reflns_number_total             2812
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01166d2.cif
_cod_data_source_block           cu_60408aa
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1554526
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.588
_shelx_estimated_absorpt_t_max   0.876
_shelx_res_checksum              73787
_shelx_hkl_checksum              16873