A catalyst-free intermolecular trans-iodoalkylation of alkynes.
Liu, Jie-Jie; Huang, Hong-Yan; Cheng, Liang; Liu, Qi; Wang, Dong; Liu, Li; Organic & biomolecular chemistry 16 (2018) 899–903; doi:10.1039/c7ob03159a

data_7156057
_publ_section_title
;
 A catalyst-free intermolecular trans-iodoalkylation of alkynes.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              899
_journal_page_last               903
_journal_paper_doi               10.1039/c7ob03159a
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C24 H20 I N O'
_chemical_formula_sum            'C24 H20 I N O'
_chemical_formula_weight         465.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-12-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2017-07-23 deposited with the CCDC.
2018-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.565(3)
_cell_length_b                   11.480(2)
_cell_length_c                   24.047(5)
_cell_measurement_reflns_used    9625
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4852
_cell_measurement_theta_min      2.1965
_cell_volume                     4020.8(14)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
scan:
    Number of images: 330
               Slice: -110.0000 - 55.0000
         Image width: 0.5000
            Exp time: 7.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 45.0655
              2theta: -20.0331
scan:
    Number of images: 120
               Slice: -5.0000 - 55.0000
         Image width: 0.5000
            Exp time: 7.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 45.0655
              2theta: -20.0331
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0535
_diffrn_orient_matrix_UB_12      0.0558
_diffrn_orient_matrix_UB_13      0.0402
_diffrn_orient_matrix_UB_21      -0.0534
_diffrn_orient_matrix_UB_22      0.0270
_diffrn_orient_matrix_UB_23      0.0336
_diffrn_orient_matrix_UB_31      0.0055
_diffrn_orient_matrix_UB_32      -0.0274
_diffrn_orient_matrix_UB_33      0.0308
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18287
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.412
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    1.606
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_description       block
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4590
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.192
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0230P)^2^+4.1850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0766
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4363
_reflns_number_total             4590
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob03159a2.cif
_cod_data_source_block           sa4505a
_cod_depositor_comments
'Adding full bibliography for 7156057--7156060.cif.'
_cod_original_cell_volume        4020.9(14)
_cod_database_code               7156057
_shelxl_version_number           2013-4
_diffrn_number_total             5114
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 I1A-C17 = I1-C17
 2.13 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
I1: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
I1 \\sim I1A: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.04
Uanis(I1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(I1A) \\sim Ueq, Uanis(I1) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(I1A)=1-FVAR(1)
 Sof(I1)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
5.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              74522
_olex2_submission_special_instructions 'No special instructions were received'