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_7156059
_publ_section_title
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 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 H19 Cl I N O'
_chemical_formula_sum            'C24 H19 Cl I N O'
_chemical_formula_weight         499.75
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-07-20
_audit_creation_method
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
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_audit_update_record
;
2017-07-23 deposited with the CCDC.
2018-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                82.895(3)
_cell_angle_beta                 86.591(3)
_cell_angle_gamma                79.419(3)
_cell_formula_units_Z            2
_cell_length_a                   9.2532(19)
_cell_length_b                   9.542(3)
_cell_length_c                   12.045(3)
_cell_measurement_reflns_used    4621
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4855
_cell_measurement_theta_min      1.4611
_cell_volume                     1036.7(5)
_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, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14417
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         2.613
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    1.688
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.64589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0339
_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^)+(0.0229P)^2^+0.4738P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0805
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4614
_reflns_number_total             4738
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob03159a2.cif
_cod_data_source_block           a_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7156057--7156060.cif.'
_cod_database_code               7156059
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.836
_shelx_estimated_absorpt_t_min   0.504
_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.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C13(H13), C14(H14), C16(H16),
 C17(H17), C19(H19), C20(H20), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              9490
_olex2_submission_special_instructions 'No special instructions were received'