An efficient synthesis of gem-diiodoolefins and (E)-iodoalkenes from propargylic amides with a Cu(i)/Cu(iii) cycle
Zhang, Shuo; Chen, Ying; Wang, Jianwu; Pan, Yue; Xu, Zhenghu; Tung, Chen-Ho; Organic Chemistry Frontiers 2 (2015) 578–; doi:10.1039/C5QO00043B

data_1553108
_publ_section_title
;
 An efficient synthesis of gem-diiodoolefins and (E)-iodoalkenes from
 propargylic amides with a Cu(i)/Cu(iii) cycle
;
_journal_issue                   5
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              578
_journal_paper_doi               10.1039/C5QO00043B
_journal_volume                  2
_journal_year                    2015
_chemical_formula_moiety         'C23 H25 N O5'
_chemical_formula_sum            'C23 H25 N O5'
_chemical_formula_weight         395.44
_chemical_name_systematic        zhangshuotrienes
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-20
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_audit_update_record
;
2015-01-31 deposited with the CCDC.
2015-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                87.764(2)
_cell_angle_beta                 69.092(3)
_cell_angle_gamma                73.409(3)
_cell_formula_units_Z            2
_cell_length_a                   9.2215(6)
_cell_length_b                   10.9612(7)
_cell_length_c                   11.6484(7)
_cell_measurement_reflns_used    7009
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      63.77
_cell_measurement_theta_min      4.07
_cell_volume                     1051.48(12)
_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-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.933
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8884
_diffrn_reflns_theta_full        63.77
_diffrn_reflns_theta_max         63.77
_diffrn_reflns_theta_min         4.07
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_refine_diff_density_max         0.735
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0095(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3233
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0539
_refine_ls_shift/su_max          1.430
_refine_ls_shift/su_mean         0.026
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0765P)^2^+0.4630P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1496
_refine_ls_wR_factor_ref         0.1513
_reflns_number_gt                3074
_reflns_number_total             3233
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5qo00043b2.cif
_cod_data_source_block           p
_cod_original_cell_volume        1051.48(11)
_cod_database_code               1553108
_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:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C16(H16), C17(H17), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'