Oxygenative and Dehydrogenative [3 + 3] Benzannulation Reactions of α,β-Unsaturated Aldehydes and γ-Phosphonyl Crotonates Mediated by Air: Regioselective Synthesis of 4-Hydroxybiaryl-2-carboxylates.
Joshi, Prabhakar Ramchandra; Nanubolu, Jagadeesh Babu; Menon, Rajeev S.; Organic letters 18 (2016) 752–755; doi:10.1021/acs.orglett.6b00016

data_1542410
_publ_section_title
;
 Oxygenative and Dehydrogenative [3 + 3] Benzannulation Reactions of
 \a,\b-Unsaturated Aldehydes and \g-Phosphonyl Crotonates Mediated by Air:
 Regioselective Synthesis of 4-Hydroxybiaryl-2-carboxylates.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              752
_journal_page_last               755
_journal_paper_doi               10.1021/acs.orglett.6b00016
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C21 H15 N O6'
_chemical_formula_sum            'C21 H15 N O6'
_chemical_formula_weight         377.34
_chemical_name_systematic
'Methyl 4-(4-nitrobenzoyloxy)biphenyl-2-carboxylate'
_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-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.980(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0698(9)
_cell_length_b                   6.5112(7)
_cell_length_c                   35.008(4)
_cell_measurement_reflns_used    4918
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.06
_cell_measurement_theta_min      2.33
_cell_volume                     1837.0(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0288
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            17617
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.866
_diffrn_reflns_theta_max         24.866
_diffrn_reflns_theta_min         1.747
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       Needle
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1975 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.237
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         6371
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.236
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0678
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+0.6009P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1427
_reflns_Friedel_coverage         0.822
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                5861
_reflns_number_total             6371
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00016_si_002.cif
_cod_data_source_block           BA96M
_cod_depositor_comments          'Adding full bibliography for 1542410.cif.'
_cod_original_cell_volume        1837.0(3)
_cod_database_code               1542410
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.958
_shelx_estimated_absorpt_t_max   0.992
_exptl_absorpt_special_details
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_shelx_res_checksum              88549
_shelx_hkl_checksum              8782