Copper-catalyzed intermolecular asymmetric propargylic dearomatization of phenol derivatives
Shao, Long; Hu, Xiang-Ping; Chem. Commun.  (2017) –; doi:10.1039/C7CC03034G

data_7120353
_publ_section_title
;
 Copper-catalyzed intermolecular asymmetric propargylic dearomatization of
 phenol derivatives
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC03034G
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_compound_source        3,4,5-trimethoxyphenol
_chemical_formula_moiety         C18H17BrO4
_chemical_formula_sum            'C18 H17 Br O4'
_chemical_formula_weight         377.23
_chemical_melting_point          163.0(10)
_chemical_name_common            (S)-3fa
_chemical_name_systematic
(S)-4-(1-(4-bromophenyl)prop-2-yn-1-yl)-3,4,5-trimethoxycyclohexa-2,5-dienone
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-03-13 deposited with the CCDC.
2017-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.474(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.6645(15)
_cell_length_b                   13.511(3)
_cell_length_c                   8.2107(16)
_cell_measurement_reflns_used    1648
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      44.533
_cell_measurement_theta_min      5.016
_cell_volume                     841.0(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0660
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5027
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.508
_exptl_absorpt_coefficient_mu    2.461
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
; 
 Flack x determined using 997 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.007(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3090
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0143P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0799
_reflns_Friedel_coverage         0.789
_reflns_Friedel_fraction_full    0.876
_reflns_Friedel_fraction_max     0.862
_reflns_number_gt                2629
_reflns_number_total             3090
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc03034g2.cif
_cod_data_source_block           cd16282
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '162-164' was changed to '163.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7120353
_shelx_estimated_absorpt_t_min   0.626
_shelx_estimated_absorpt_t_max   0.757
_shelxl_version_number           2013-4
_shelx_res_checksum              8612
_shelx_hkl_checksum              5572