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_7118504
_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_absolute_configuration unk
_chemical_formula_moiety         'C20 H20 O3 S'
_chemical_formula_sum            'C20 H20 O3 S'
_chemical_formula_weight         340.42
_chemical_name_common            wjp2014_10_9
_chemical_name_systematic
'tert-butyl 2-methyl-5-phenyl-4-(thiophen-2-yl)furan-3-carboxylate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-10-12
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2015-10-21 deposited with the CCDC.
2015-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2716(5)
_cell_length_b                   11.6329(6)
_cell_length_c                   17.2262(9)
_cell_measurement_reflns_used    2706
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5492
_cell_measurement_theta_min      3.0421
_cell_volume                     1857.94(17)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0058238000
_diffrn_orient_matrix_UB_12      -0.0114713000
_diffrn_orient_matrix_UB_13      0.0403187000
_diffrn_orient_matrix_UB_21      -0.0752525000
_diffrn_orient_matrix_UB_22      0.0105332000
_diffrn_orient_matrix_UB_23      -0.0017728000
_diffrn_orient_matrix_UB_31      -0.0123171000
_diffrn_orient_matrix_UB_32      -0.0589713000
_diffrn_orient_matrix_UB_33      -0.0081713000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12260
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.05
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98285
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         1947
_refine_ls_number_restraints     131
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0608P)^2^+0.3290P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1175
_reflns_number_gt                1461
_reflns_number_total             1947
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc09137c2.cif
_cod_data_source_block           151012_wjp2014_10_9_cw
_cod_original_cell_volume        1857.95(17)
_cod_database_code               7118504
_chemical_oxdiff_formula         'c10 h10 n2 o8'
_reflns_odcompleteness_completeness 99.55
_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. Restrained distances
 C11A-C12A
 1.4 with sigma of 0.02
 C13A-C12A
 1.4 with sigma of 0.02
 C14A-C13A
 1.5 with sigma of 0.02
 C11-C8
 1.5 with sigma of 0.02
 C11A-C8
 1.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
S1 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim S1A \\sim C12A \\sim C13A
\\sim C14A \\sim C11A: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.02
4. Others
 Sof(S1A)=Sof(C11A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=
 Sof(H14A)=1-FVAR(1)
 Sof(S1)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14),
 C12A(H12A), C13A(H13A), C14A(H14A)
5.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
;