Palladium-catalyzed acetalization/cyclization of enynones with alcohols: rapid access to functionalized dihaloalkenyl dihydrofurans.
Ma, Ruize; Chen, Yang; Fang, Songjia; Jiang, Huanfeng; Yang, Shaorong; Wu, Wanqing; Chemical communications (Cambridge, England)  (2022) –; doi:10.1039/d2cc03949d

data_7131048
_publ_section_title
;
 Palladium-catalyzed acetalization/cyclization of enynones with alcohols:
 rapid access to functionalized dihaloalkenyl dihydrofurans.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d2cc03949d
_journal_year                    2022
_chemical_formula_moiety         'C11 H14 Br2 O4'
_chemical_formula_sum            'C11 H14 Br2 O4'
_chemical_formula_weight         370.04
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-11-03 deposited with the CCDC.	2022-11-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.4480(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5383(2)
_cell_length_b                   18.4779(5)
_cell_length_c                   11.2222(4)
_cell_measurement_reflns_used    6047
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.340
_cell_measurement_theta_min      2.861
_cell_volume                     1349.68(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      170.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14947
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.380
_diffrn_reflns_theta_min         2.204
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.006
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0835 before and 0.0478 after correction. The Ratio of minimum to maximum transmission is 0.6368. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2754
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0259
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0294P)^2^+0.5675P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0553
_refine_ls_wR_factor_ref         0.0608
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2260
_reflns_number_total             2754
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03949d2.cif
_cod_data_source_block           wyd_0m
_cod_original_cell_volume        1349.67(7)
_cod_database_code               7131048
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.558
_shelx_estimated_absorpt_t_min   0.315
_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
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C6(H6A,H6B,H6C), C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'