Rh(III)-Catalyzed Dual C-H Functionalization/Cyclization Cascade by a Removable Directing Group: A Method for Synthesis of Polycyclic Fused Pyrano[<i>de</i>]Isochromenes.
Shu, Zhihao; Zhou, Jianhui; Li, Junyou; Cheng, Yilang; Liu, Hong; Wang, Dechuan; Zhou, Yu; The Journal of organic chemistry 85 (2020) 12097–12107; doi:10.1021/acs.joc.0c01228

data_4038789
_publ_section_title
;
 Rh(III)-Catalyzed Dual C-H Functionalization/Cyclization Cascade by a
 Removable Directing Group: A Method for Synthesis of Polycyclic Fused
 Pyrano[<i>de</i>]Isochromenes.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12097
_journal_page_last               12107
_journal_paper_doi               10.1021/acs.joc.0c01228
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C17 H22 O8 P2'
_chemical_formula_sum            'C17 H22 O8 P2'
_chemical_formula_weight         416.28
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.949(8)
_cell_angle_gamma                90
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_cell_length_a                   22.428(5)
_cell_length_b                   8.079(2)
_cell_length_c                   10.933(3)
_cell_measurement_reflns_used    2538
_cell_measurement_temperature    295
_cell_measurement_theta_max      26.232
_cell_measurement_theta_min      3.179
_cell_volume                     1938.1(8)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      295.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_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  0.0611
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10721
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.413
_diffrn_reflns_theta_min         3.180
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1265 before and 0.0542 after correction. The Ratio of minimum to maximum transmission is 0.9353. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         1980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0486
_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^)+(0.0465P)^2^+2.2661P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1253
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1351
_reflns_number_total             1980
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01228_si_003.cif
_cod_data_source_block           22019736szh0702_0m
_cod_depositor_comments
'Adding full bibliography for 4038788--4038790.cif.'
_cod_original_cell_volume        1938.2(9)
_cod_database_code               4038789
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.951
_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. Others
 Fixed Sof: C6(0.5) H6(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10)
3.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C2(H2A,H2B,H2C), C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'