The Ireland-Claisen rearrangement strategy towards the synthesis of the schizophrenia drug, (+)-asenapine.
Anugu, Raghunath Reddy; Mainkar, Prathama S.; Sridhar, Balasubramanian; Chandrasekhar, Srivari; Organic & biomolecular chemistry 14 (2016) 1332–1337; doi:10.1039/c5ob02047f

data_7154814
_publ_section_title
;
 The Ireland-Claisen rearrangement strategy towards the synthesis of the
 schizophrenia drug, (+)-asenapine.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1332
_journal_page_last               1337
_journal_paper_doi               10.1039/c5ob02047f
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C20 H19 Br Cl O3'
_chemical_formula_sum            'C20 H19 Br Cl O3'
_chemical_formula_weight         422.71
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-06-18 deposited with the CCDC.
2015-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.148(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.241(3)
_cell_length_b                   9.598(4)
_cell_length_c                   25.276(10)
_cell_measurement_reflns_used    2533
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      19.98
_cell_measurement_theta_min      2.27
_cell_volume                     1973.8(13)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT Bruker, 2001'
_computing_molecular_graphics    'SHELXL2014 (Sheldrick, 2015)'
_computing_publication_material  'SHELXL2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_unetI/netI     0.0705
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            14919
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.632
_exptl_absorpt_coefficient_mu    2.233
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker,2001'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       needle
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.934
_refine_diff_density_min         -0.846
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3470
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.169
_refine_ls_R_factor_all          0.1841
_refine_ls_R_factor_gt           0.1232
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1164P)^2^+16.5775P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3237
_refine_ls_wR_factor_ref         0.3589
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1919
_reflns_number_total             3470
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob02047f2.cif
_cod_data_source_block           ay01
_cod_depositor_comments          'Adding full bibliography for 7154814.cif.'
_cod_database_code               7154814
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              91716