Gold-Catalyzed Diastereoselective Formal Intermolecular [4 + 2 + 1] Cycloaddition of 1,3-Dien-8-yne with Diazo Ester.
Wang, Yu-Jiang; Li, Xiao-Xiao; Chen, Zili; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00146

data_4038488
_publ_section_title
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 Gold-Catalyzed Diastereoselective Formal Intermolecular [4 + 2 + 1]
 Cycloaddition of 1,3-Dien-8-yne with Diazo Ester.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00146
_journal_year                    2020
_chemical_formula_moiety         'C24 H26 N O4 S'
_chemical_formula_sum            'C24 H26 N O4 S'
_chemical_formula_weight         424.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-12-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.11
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6268(11)
_cell_length_b                   13.5454(14)
_cell_length_c                   12.6269(11)
_cell_measurement_reflns_used    9308
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.934
_cell_measurement_theta_min      2.220
_cell_volume                     2132.4(3)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      199.98
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29074
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.298
_diffrn_reflns_theta_min         2.220
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1401 before and 0.0629 after correction. The Ratio of minimum to maximum transmission is 0.7668. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             900
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5089
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0532
_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^)+(0.0614P)^2^+1.1454P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1473
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3476
_reflns_number_total             5089
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00146_si_002.cif
_cod_data_source_block           mo_wyj2019052301_0ma_a
_cod_database_code               4038488
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.968
_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:
 N005(H005), C00F(H00F)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00B,H00C), C00C(H00D,H00E), C00K(H00J,H00K)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00A), C00G(H00G), C00H(H00H), C00I(H00I), C00L(H00L),
 C00M(H00M), C00N(H00N), C00P(H00P), C00R(H00S), C00S(H00T), C00T(H00U)
2.d Idealised Me refined as rotating group:
 C00Q(H00O,H00Q,H00R), C00U(H00V,H00W,H00X)
;
_shelx_res_checksum              65001
_shelx_hkl_checksum              67294
_olex2_submission_special_instructions 'No special instructions were received'