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_1553107
_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         'C10 H7 I2 N O'
_chemical_formula_sum            'C17 H0 I2 N3 O6'
_chemical_formula_weight         596.00
_chemical_name_systematic        diiodide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-01-05
_audit_creation_method
;
Olex2 1.2
(compiled 2014.12.26 svn.r3119 for OlexSys, GUI svn.r4975)
;
_audit_update_record
;
2015-01-31 deposited with the CCDC.
2015-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.113(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5881(2)
_cell_length_b                   18.9850(6)
_cell_length_c                   10.6706(4)
_cell_measurement_reflns_used    2923
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      63.733
_cell_measurement_theta_min      4.659
_cell_volume                     1129.13(7)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.884
_diffrn_measured_fraction_theta_max 0.963
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1088
_diffrn_reflns_av_unetI/netI     0.1102
_diffrn_reflns_Laue_measured_fraction_full 0.884
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5016
_diffrn_reflns_point_group_measured_fraction_full 0.884
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         63.733
_diffrn_reflns_theta_min         4.658
_exptl_absorpt_coefficient_mu    44.378
_exptl_crystal_density_diffrn    3.506
_exptl_crystal_F_000             1108
_refine_diff_density_max         6.024
_refine_diff_density_min         -2.001
_refine_diff_density_rms         0.579
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.212
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.212
_refine_ls_R_factor_all          0.1236
_refine_ls_R_factor_gt           0.1113
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2803
_refine_ls_wR_factor_ref         0.2931
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1481
_reflns_number_total             1807
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5qo00043b2.cif
_cod_data_source_block           test
_cod_database_code               1553107
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7), C10(H10)
;
_olex2_submission_special_instructions 'No special instructions were received'