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_4038487
_publ_section_title
;
 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         'C18 H20 O4'
_chemical_formula_sum            'C18 H20 O4'
_chemical_formula_weight         300.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-05-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.8967(9)
_cell_length_b                   11.4613(10)
_cell_length_c                   30.389(3)
_cell_measurement_reflns_used    5092
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      26.416
_cell_measurement_theta_min      2.683
_cell_volume                     3098.7(5)
_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)'
_diffrn_ambient_temperature      190.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_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  0.0650
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            20167
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         2.684
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1166 before and 0.0605 after correction. The Ratio of minimum to maximum transmission is 0.7971. 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    1.288
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1509 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.2(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         6705
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.911
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.0525
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1581
_reflns_Friedel_coverage         0.861
_reflns_Friedel_fraction_full    0.946
_reflns_Friedel_fraction_max     0.890
_reflns_number_gt                4131
_reflns_number_total             6705
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00146_si_002.cif
_cod_data_source_block           mo_wyj20190524041_0m
_cod_depositor_comments
;

2025-07-29
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C18 H20 O4)'
_cod_original_formula_sum        'C36 H40 O8'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     600.68
_cod_database_code               4038487
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.985
_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:
 C2(H2), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C13(H13A,H13B), C16(H16A,H16B), C19(H19A,H19B), C33(H33A,H33B),
 C34(H34A,H34B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C8(H8), C14(H14), C15(H15), C17(H17), C18(H18), C22(H22),
 C25(H25), C26(H26), C31(H31), C32(H32), C35(H35), C36(H36)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C28(H28A,H28B,H28C), C30(H30A,H30B,
 H30C)
;
_shelx_res_checksum              32261
_shelx_hkl_checksum              78388
_olex2_submission_special_instructions 'No special instructions were received'