Lewis Acid-Catalyzed Annulative Partial Dimerization of 3-Aryloxyacrylates to 4-Arylchroman-2-ones: Synthesis of Analogues of Tolterodine, RORγ Inhibitor and a GPR40 Agonist
Fernandes, Rodney Agustinho; Kunkalkar, Rupesh A.; Chemical Communications  (2019) –; doi:10.1039/C8CC09785B

data_7122905
_publ_section_title
;
 Lewis Acid-Catalyzed Annulative Partial Dimerization of
 3-Aryloxyacrylates to 4-Arylchroman-2-ones: Synthesis of Analogues of
 Tolterodine, ROR\g Inhibitor and a GPR40 Agonist
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC09785B
_journal_year                    2019
_chemical_formula_moiety         'C19 H20 O3'
_chemical_formula_sum            'C19 H20 O3'
_chemical_formula_weight         296.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-08-29
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-10-16 deposited with the CCDC.
2019-01-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.6777(10)
_cell_length_b                   15.169(6)
_cell_length_c                   8.027(3)
_cell_measurement_reflns_used    2167
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.1
_cell_measurement_theta_min      3.1
_cell_volume                     3126.6(17)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
scan:
    Number of images: 223
               Slice: -92.5000 - 19.0000
         Image width: 0.5000
            Exp time: 16.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: 108.0000
                 XTD: 44.8693
              2theta: -19.9963
scan:
    Number of images: 161
               Slice: -42.5000 - 38.0000
         Image width: 0.5000
            Exp time: 16.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 72.0000
                 Phi: 36.0000
                 XTD: 44.8693
              2theta: -19.9963
scan:
    Number of images: 258
               Slice: -59.0000 - 70.0000
         Image width: 0.5000
            Exp time: 16.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 72.0000
                 Phi: 108.0000
                 XTD: 44.8693
              2theta: -19.9963
scan:
    Number of images: 150
               Slice: -61.0000 - 14.0000
         Image width: 0.5000
            Exp time: 16.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: -180.0000
                 XTD: 44.8693
              2theta: -19.9963
scan:
    Number of images: 60
               Slice: -14.5000 - 15.5000
         Image width: 0.5000
            Exp time: 16.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: -108.0000
                 XTD: 44.8693
              2theta: -19.9963
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       XPlain
_diffrn_orient_matrix_UB_11      -0.002659
_diffrn_orient_matrix_UB_12      -0.038753
_diffrn_orient_matrix_UB_13      0.002785
_diffrn_orient_matrix_UB_21      -0.023209
_diffrn_orient_matrix_UB_22      -0.002837
_diffrn_orient_matrix_UB_23      -0.061638
_diffrn_orient_matrix_UB_31      0.116294
_diffrn_orient_matrix_UB_32      -0.011090
_diffrn_orient_matrix_UB_33      -0.043279
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13130
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.119
_diffrn_source                   MicroMax003_Mo
_diffrn_source_current           0.6
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       needle
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2743
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0555
_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^)+(0.0622P)^2^+1.2656P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1316
_refine_ls_wR_factor_ref         0.1395
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2328
_reflns_number_total             2743
_reflns_shell_number_unique_all  4712
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc09785b2.cif
_cod_data_source_block           shelxl
_cod_database_code               7122905
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C1(H1A), C9(H9), C11(H11)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C16(H16A,H16B,H16C), C18(H18A,H18B,
 H18C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              1636
_shelx_hkl_checksum              66790
_olex2_submission_special_instructions 'No special instructions were received'