Highly regio- and diastereoselective (3+3)-cycloannulation of carbonyl ylides and 2-(1-alkynyl)-2-alken-1-ones enabled by silver catalysis
Barman, Jyotish; Pan, Subhas Chandra; Chemical Communications 61 (2025) 9119–9122; doi:10.1039/D5CC02003D

data_7134552
_publ_section_title
;
 Highly regio- and diastereoselective (3+3)-cycloannulation of carbonyl
 ylides and 2-(1-alkynyl)-2-alken-1-ones enabled by silver catalysis
;
_journal_issue                   50
_journal_name_full               'Chemical Communications'
_journal_page_first              9119
_journal_page_last               9122
_journal_paper_doi               10.1039/D5CC02003D
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C35 H27 Br O4'
_chemical_formula_sum            'C35 H27 Br O4'
_chemical_formula_weight         591.505
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-03-01
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb2 for OlexSys, GUI svn.r6869)
;
_audit_update_record
;
2025-03-02 deposited with the CCDC.	2025-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.237(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.213(5)
_cell_length_b                   7.777(2)
_cell_length_c                   25.463(7)
_cell_measurement_reflns_used    9801
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      24.64
_cell_measurement_theta_min      2.45
_cell_volume                     3288.8(16)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_diffrn_ambient_temperature      295.00
_diffrn_measured_fraction_theta_full 0.9961
_diffrn_measured_fraction_theta_max 0.9903
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.9961
_diffrn_reflns_Laue_measured_fraction_max 0.9903
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            77508
_diffrn_reflns_point_group_measured_fraction_full 0.9961
_diffrn_reflns_point_group_measured_fraction_max 0.9903
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         2.47
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.283
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4709
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1432 before and 0.0580 after correction.
The Ratio of minimum to maximum transmission is 0.6319.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_description       block
_exptl_crystal_F_000             1215.911
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.7074
_refine_diff_density_min         -0.7336
_refine_diff_density_rms         0.0591
_refine_ls_d_res_high            0.8286
_refine_ls_d_res_low             8.2557
_refine_ls_goodness_of_fit_ref   1.0244
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    49
_refine_ls_number_parameters     363
_refine_ls_number_reflns         6001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0244
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          -0.0010
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0661P)^2^+1.9262P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1310
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -20
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              30
_reflns_limit_l_min              -14
_reflns_number_gt                4779
_reflns_number_total             6001
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5cc02003d2.cif
_cod_data_source_block           JB_DY_0m_a
_cod_depositor_comments          'Adding full bibliography for 7134552.cif.'
_cod_original_cell_volume        3288.9(16)
_cod_original_formula_sum        'C35 H27 Br1 O4'
_cod_database_code               7134552
_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:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15a,H15b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C19(H19), C20(H20), C21(H21),
 C22(H22), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C31(H31), C32(H32),
  C34(H34), C35(H35)
2.d Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c), C16(H16a,H16b,H16c)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'