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_4038788
_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         'C22 H32 N2 O9 P2'
_chemical_formula_sum            'C22 H32 N2 O9 P2'
_chemical_formula_weight         530.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 113.590(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.246(3)
_cell_length_b                   21.331(5)
_cell_length_c                   12.725(2)
_cell_measurement_reflns_used    2739
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.036
_cell_measurement_theta_min      2.376
_cell_volume                     2548.7(10)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 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      150.0
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1002
_diffrn_reflns_av_unetI/netI     0.1095
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18164
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         1.990
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6373
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0964 before and 0.0676 after correction. The Ratio of minimum to maximum transmission is 0.8550. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       needle
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         5096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1398
_refine_ls_R_factor_gt           0.0640
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0557P)^2^+1.1150P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1550
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2847
_reflns_number_total             5096
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01228_si_004.cif
_cod_data_source_block           mo_22020028_0m
_cod_depositor_comments
'Adding full bibliography for 4038788--4038790.cif.'
_cod_original_cell_volume        2548.9(10)
_cod_database_code               4038788
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C8(H8), C9(H9)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C5(H5A,H5B,H5C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C), C1(H1A,H1B,H1C), C22(H22A,H22B,H22C), C4(H4A,H4B,
 H4C)
;
_olex2_submission_special_instructions 'No special instructions were received'