Rhodium-catalyzed highly diastereoselective intramolecular [4 + 2] cycloaddition of 1,3-disubstituted allene-1,3-dienes
Han, Yulin; Ma, Shengming; Organic Chemistry Frontiers 5 (2018) 2680–; doi:10.1039/C8QO00650D

data_1554376
_publ_section_title
;
 Rhodium-catalyzed highly diastereoselective intramolecular [4 + 2]
 cycloaddition of 1,3-disubstituted allene-1,3-dienes
;
_journal_issue                   18
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2680
_journal_paper_doi               10.1039/C8QO00650D
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C24 H30 O4'
_chemical_formula_sum            'C24 H30 O4'
_chemical_formula_weight         382.48
_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     direct
_audit_creation_date             2016-07-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-09-18 deposited with the CCDC.
2018-07-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.151(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9632(10)
_cell_length_b                   26.894(3)
_cell_length_c                   9.2793(10)
_cell_measurement_reflns_used    5442
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.64
_cell_measurement_theta_min      2.27
_cell_volume                     2099.9(4)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21185
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.925
_diffrn_reflns_theta_min         2.420
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0626 before and 0.0454 after correction.
The Ratio of minimum to maximum transmission is 0.8325.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         6552
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0506P)^2^+0.4595P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1227
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4462
_reflns_number_total             6552
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00650d2.cif
_cod_data_source_block           mo_dm16454_0m
_cod_database_code               1554376
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C8(H8A,H8B), C9(H9A,H9B), C14(H14A,H14B), C15(H15A,H15B),
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C17(H17A,H17B,H17C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              35263
_shelx_hkl_checksum              70096
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'