Calcium-catalyzed regioselective dehydrative cross-coupling of propargylic alcohols with 1,3-dicarbonyl compounds
Xie, Peizhong; Wo, Xiangyang; Yang, Xiaobo; Cai, Xinying; Li, Shuangshuang; Gao, Cuiqing; Fu, Weishan; Sun, Zuolian; Loh, Teck-Peng; Green Chemistry 21 (2019) 5207–; doi:10.1039/C9GC02635E

data_7233621
_publ_section_title
;
 Calcium-catalyzed regioselective dehydrative cross-coupling of
 propargylic alcohols with 1,3-dicarbonyl compounds
;
_journal_issue                   19
_journal_name_full               'Green Chemistry'
_journal_page_first              5207
_journal_paper_doi               10.1039/C9GC02635E
_journal_volume                  21
_journal_year                    2019
_chemical_formula_sum            'C23 H22 O3'
_chemical_formula_weight         346.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc229b80
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-05-13 deposited with the CCDC.    2019-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.025(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3670(7)
_cell_length_b                   15.8302(10)
_cell_length_c                   11.4198(7)
_cell_measurement_reflns_used    9659
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      53.89
_cell_measurement_theta_min      3.70
_cell_volume                     1876.9(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12903
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        52.983
_diffrn_reflns_theta_max         52.983
_diffrn_reflns_theta_min         4.024
_exptl_absorpt_coefficient_mu    0.406
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3300
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0483P)^2^+0.5020P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1103
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2992
_reflns_number_total             3300
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc02635e2.cif
_cod_data_source_block           20190322ZH_NGD_XXD_0m_a
_cod_depositor_comments
'Adding full bibliography for 7233620--7233621.cif.'
_cod_database_code               7233621
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.927
_shelx_estimated_absorpt_t_max   0.945
_shelx_res_checksum              71841