A gold-catalyzed 1,2-acyloxy migration/intramolecular cyclopropanation/ring enlargement cascade: syntheses of medium-sized heterocycles
Yin-Wei Sun; Xiang-Ying Tang; Min Shi; Chem.Commun. 51 (2015) 13937–; doi:10.1039/C5cc05808B

data_7117727
_publ_section_title
;
 A gold-catalyzed 1,2-acyloxy migration/intramolecular
 cyclopropanation/ring enlargement cascade: syntheses of medium-sized
 heterocycles
;
_journal_name_full               Chem.Commun.
_journal_page_first              13937
_journal_paper_doi               10.1039/C5cc05808B
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C25 H26 N2 O4 S'
_chemical_formula_sum            'C25 H26 N2 O4 S'
_chemical_formula_weight         450.54
_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_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-05-15
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-05-18 deposited with the CCDC.
2015-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.772(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.5847(12)
_cell_length_b                   17.5982(16)
_cell_length_c                   20.1268(18)
_cell_measurement_reflns_used    3643
_cell_measurement_temperature    130
_cell_measurement_theta_max      25.54
_cell_measurement_theta_min      2.20
_cell_volume                     4452.2(7)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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  0.0733
_diffrn_reflns_av_unetI/netI     0.0851
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            44683
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.645
_diffrn_reflns_theta_min         1.538
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0806 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.8850.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     583
_refine_ls_number_reflns         13643
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0565
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0581P)^2^+0.1075P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1473
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7555
_reflns_number_total             13643
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc05808b2.cif
_cod_data_source_block           mo_dm15389_0m
_cod_database_code               7117727
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.956
_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 Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7A,H7B), C26(H26A,H26B), C32(H32A,H32B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20),
 C21(H21), C23(H23), C24(H24), C28(H28), C29(H29), C39(H39), C40(H40), C41(H41),
  C42(H42), C43(H43), C45(H45), C46(H46), C48(H48), C49(H49)
2.c X=CH2 refined with riding coordinates:
 C10(H10A,H10B), C35(H35A,H35B)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C12(H12A,H12B,H12C), C25(H25A,H25B,H25C), C33(H33A,H33B,
 H33C), C37(H37A,H37B,H37C), C50(H50A,H50B,H50C)
;
_shelx_res_checksum              58988
_olex2_submission_special_instructions 'No special instructions were received'