Synthesis of Isocoumarins from Cyclic 2-Diazo-1,3-diketones and Benzoic Acids via Rh(III)-Catalyzed C-H Activation and Esterification.
Yang, Cheng; He, Xinwei; Zhang, Lanlan; Han, Guang; Zuo, Youpeng; Shang, Yongjia; The Journal of organic chemistry 82 (2017) 2081–2088; doi:10.1021/acs.joc.6b02906

data_4032159
_publ_section_title
;
 Synthesis of Isocoumarins from Cyclic 2-Diazo-1,3-diketones and Benzoic
 Acids via Rh(III)-Catalyzed C-H Activation and Esterification.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2081
_journal_page_last               2088
_journal_paper_doi               10.1021/acs.joc.6b02906
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C12 H9 Br O3'
_chemical_formula_weight         281.10
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.476(2)
_cell_length_b                   12.9994(17)
_cell_length_c                   5.4283(7)
_cell_measurement_reflns_used    4781
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.17
_cell_measurement_theta_min      2.63
_cell_volume                     1092.1(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            8816
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    3.751
_exptl_absorpt_correction_T_max  0.5064
_exptl_absorpt_correction_T_min  0.4540
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.93(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2413
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0699P)^2^+2.0609P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1435
_reflns_number_gt                2090
_reflns_number_total             2413
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02906_si_003.cif
_cod_data_source_block           op
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 4032159--4032161.cif.
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_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               4032159