Transition-Metal-Free Synthesis of 2-Substituted Methyl Benzo[b]furan-3-carboxylates.
Kang, Byungsoo; Lee, Min Hyung; Kim, Mijung; Hwang, Jungwoon; Kim, Hyeong Baik; Chi, Dae Yoon; The Journal of organic chemistry 80 (2015) 8254–8261; doi:10.1021/acs.joc.5b01311

data_4031340
_publ_section_title
;
 Transition-Metal-Free Synthesis of 2-Substituted Methyl
 Benzo[b]furan-3-carboxylates.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8254
_journal_page_last               8261
_journal_paper_doi               10.1021/acs.joc.5b01311
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C19 H12 O3'
_chemical_formula_sum            'C19 H12 O3'
_chemical_formula_weight         288.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-10-10
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.938(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.518(5)
_cell_length_b                   6.2369(11)
_cell_length_c                   21.082(5)
_cell_measurement_reflns_used    8980
_cell_measurement_temperature    267.5
_cell_measurement_theta_max      25.07
_cell_measurement_theta_min      3.26
_cell_volume                     2783.3(10)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      267.5
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0862
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            51948
_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         26.015
_diffrn_reflns_theta_min         2.287
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.7031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0671 before and 0.0634 after correction.
The Ratio of minimum to maximum transmission is 0.9434.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2743
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0459P)^2^+1.2058P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.1038
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1991
_reflns_number_total             2743
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01311_si_001.cif
_cod_data_source_block           BS-14-33
_cod_depositor_comments          'Adding full bibliography for 4031340.cif.'
_cod_database_code               4031340
_shelxl_version_number           2014-3
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H22(0.08) H4(0.066) H5(0.067) H6(0.064) H7(0.055) H12(0.051)
 H13(0.054) H15(0.066) H16(0.079) H17(0.077) H18(0.061) H20(0.047)
 Fixed X: H22(0.4308) H4(0.4858) H5(0.3991) H6(0.3082) H7(0.3011) H12(0.3328)
 H13(0.2406) H15(0.1338) H16(0.0576) H17(0.0694) H18(0.1599) H20(0.2702)
 Fixed Y: H22(-0.4248) H4(0.3434) H5(0.5715) H6(0.5) H7(0.2061) H12(0.1388)
 H13(0.2061) H15(0.0847) H16(-0.1718) H17(-0.4893) H18(-0.5555) H20(-0.4467)
 Fixed Z: H22(-0.0399) H4(0.1638) H5(0.1398) H6(0.0516) H7(-0.0178) H12(-
 0.1247) H13(-0.2108) H15(-0.2869) H16(-0.3176) H17(-0.2567) H18(-0.1679) H20(-
 0.0993)
;
_olex2_submission_special_instructions 'No special instructions were received'