2-Arylcyclopropylmethanol as a substitute for homoallyl aryl alcohol in the construction of cis-2,6-disubstituted tetrahydropyran: synthesis of (+/-)-centrolobine
Veejendra K. Yadav; Ashish K. Verma; Piyush Kumar; Vijaykumar Hulikal; Chem.Commun. 50 (2014) 15457–; doi:10.1039/C4cc07796B

data_7116050
_publ_section_title
;
 2-Arylcyclopropylmethanol as a substitute for homoallyl aryl alcohol in
 the construction of cis-2,6-disubstituted tetrahydropyran: synthesis of
 (+/-)-centrolobine
;
_journal_name_full               Chem.Commun.
_journal_page_first              15457
_journal_paper_doi               10.1039/C4cc07796B
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C27 H29 Cl O3'
_chemical_formula_weight         436.95
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.310(6)
_cell_length_b                   8.664(6)
_cell_length_c                   65.12(4)
_cell_measurement_temperature    283(2)
_cell_volume                     4688(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      283(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.908
_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  0.0681
_diffrn_reflns_av_sigmaI/netI    0.0659
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       70
_diffrn_reflns_limit_l_min       -86
_diffrn_reflns_number            19076
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.16
_diffrn_reflns_theta_min         0.63
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.9741
_exptl_absorpt_correction_T_min  0.9705
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       0.0036(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         5205
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.1715
_refine_ls_R_factor_gt           0.0776
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1805
_refine_ls_wR_factor_ref         0.2468
_reflns_number_gt                2137
_reflns_number_total             5205
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc07796b2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7116050