Silver-Catalyzed Domino Hydroarylation/Cycloisomerization Reactions of ortho-Alkynylbenzaldehydes: An Entry to Functionalized Isochromene Derivatives.
Mariaule, Gaëlle; Newsome, Gregory; Toullec, Patrick Y.; Belmont, Philippe; Michelet, Véronique; Organic letters 16 (2014) 4570–; doi:10.1021/ol5021256

data_1517402
_publ_section_title
;
 Silver-Catalyzed Domino Hydroarylation/Cycloisomerization Reactions of
 ortho-Alkynylbenzaldehydes: An Entry to Functionalized Isochromene
 Derivatives.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4570
_journal_paper_doi               10.1021/ol5021256
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C24 H21 Br O4,0.25 (C H2 Cl2)'
_chemical_formula_sum            'C24.25 H21.5 Br Cl0.5 O4'
_chemical_formula_weight         474.55
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                115.0760(10)
_cell_angle_beta                 103.3320(10)
_cell_angle_gamma                92.5870(10)
_cell_formula_units_Z            4
_cell_length_a                   11.2333(3)
_cell_length_b                   13.7701(3)
_cell_length_c                   15.8106(4)
_cell_measurement_reflns_used    9783
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      3.21
_cell_volume                     2126.93(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multi layer miror'
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33923
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.381
_diffrn_reflns_theta_min         3.211
_exptl_absorpt_coefficient_mu    3.447
_exptl_absorpt_correction_T_max  0.585
_exptl_absorpt_correction_T_min  0.488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS, Bruker AXS Inc., Madison, 
Wisconsin, USA. 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blcok
_exptl_crystal_F_000             970
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.00035(3)
_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   1.221
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     593
_refine_ls_number_reflns         7699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.221
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0509
_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^)+(0.0047P)^2^+4.0085P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1050
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7483
_reflns_number_total             7699
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5021256_si_001.cif
_cod_data_source_block           gm521_0m
_cod_depositor_comments          'Adding full bibliography for 1517402.cif.'
_cod_original_cell_volume        2126.92(9)
_cod_original_formula_sum        'C24.25 H21.50 Br Cl0.50 O4'
_cod_database_code               1517402
_shelxl_version_number           2013-4
_shelx_res_checksum              79741
_shelx_hkl_checksum              90842