Rhodium-catalyzed tunable oxidative cyclization toward the selective synthesis of α-pyrones and furans.
Wu, Jiaping; Wang, Dongxu; Wan, Yanjun; Ma, Cheng; Chemical communications (Cambridge, England) 52 (2016) 1661–1664; doi:10.1039/c5cc09137c

data_7118502
_publ_section_title
;
 Rhodium-catalyzed tunable oxidative cyclization toward the selective
 synthesis of \a-pyrones and furans.
;
_journal_issue                   8
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1661
_journal_page_last               1664
_journal_paper_doi               10.1039/c5cc09137c
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C24 H17 Br O3'
_chemical_formula_sum            'C24 H17 Br O3'
_chemical_formula_weight         433.29
_chemical_name_common
'Methyl 2-(4-bromophenyl)-4,5-diphenylfuran-3-carboxylate'
_chemical_name_systematic        wip2014-9-3
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-09-28
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2015-10-07 deposited with the CCDC.
2015-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                68.569(8)
_cell_angle_beta                 80.101(6)
_cell_angle_gamma                67.458(8)
_cell_formula_units_Z            2
_cell_length_a                   9.7030(6)
_cell_length_b                   10.0809(10)
_cell_length_c                   11.7856(9)
_cell_measurement_reflns_used    1943
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5861
_cell_measurement_theta_min      3.4075
_cell_volume                     990.43(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0097406000
_diffrn_orient_matrix_UB_12      0.0674188000
_diffrn_orient_matrix_UB_13      0.0115271000
_diffrn_orient_matrix_UB_21      0.0513665000
_diffrn_orient_matrix_UB_22      0.0167942000
_diffrn_orient_matrix_UB_23      -0.0488260000
_diffrn_orient_matrix_UB_31      -0.0594946000
_diffrn_orient_matrix_UB_32      0.0410060000
_diffrn_orient_matrix_UB_33      -0.0408538000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6231
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.41
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0290P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0879
_reflns_number_gt                2846
_reflns_number_total             3617
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc09137c2.cif
_cod_data_source_block           140926_wjp2014_9_3_cw_2
_cod_original_cell_volume        990.44(14)
_cod_database_code               7118502
_chemical_oxdiff_formula         'c10 h10 n2 o8 Br1'
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;