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_7122904
_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         '0.67(C18 H18 O3)'
_chemical_formula_sum            'C12 H12 O2'
_chemical_formula_weight         188.22
_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
_atom_sites_solution_primary     dual
_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                 93.360(9)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   5.2851(6)
_cell_length_b                   11.5101(10)
_cell_length_c                   23.475(2)
_cell_measurement_reflns_used    2167
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.2360
_cell_measurement_theta_min      2.4620
_cell_volume                     1425.6(2)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_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      293(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -110.00  70.00   0.50    8.00    --  -20.00   0.00-180.00  360
  2  \w    -76.50 -53.50   0.50    8.00    --  -20.00 -72.00 108.00   46
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0662869000
_diffrn_orient_matrix_UB_12      0.0366789000
_diffrn_orient_matrix_UB_13      -0.0183175000
_diffrn_orient_matrix_UB_21      -0.0210906000
_diffrn_orient_matrix_UB_22      -0.0404751000
_diffrn_orient_matrix_UB_23      -0.0225688000
_diffrn_orient_matrix_UB_31      -0.1149740000
_diffrn_orient_matrix_UB_32      0.0285389000
_diffrn_orient_matrix_UB_33      -0.0084734000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_unetI/netI     0.0855
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            5338
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         1.738
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.037
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0566
_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^)+(0.0541P)^2^+0.4292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1507
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1711
_reflns_number_total             2453
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc09785b2.cif
_cod_data_source_block           raf-rkv-26-pc-mix_mo
_cod_database_code               7122904
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 84.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.94
_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:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C16(H16), C7(H7), C13(H13), C15(H15)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C), C1(H1A,H1B,H1C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              56688
_shelx_hkl_checksum              49681
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.561
_oxdiff_exptl_absorpt_empirical_full_min 0.738