Selective oxygenation of alkynes: a direct approach to diketones and vinyl acetate.
Xia, Xiao-Feng; Gu, Zhen; Liu, Wentao; Wang, Ningning; Wang, Haijun; Xia, Yongmei; Gao, Haiyan; Liu, Xiang; Organic & biomolecular chemistry 12 (2014) 9909–9913; doi:10.1039/c4ob01404a

data_7154140
_publ_section_title
;
 Selective oxygenation of alkynes: a direct approach to diketones and
 vinyl acetate.
;
_journal_issue                   48
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9909
_journal_page_last               9913
_journal_paper_doi               10.1039/c4ob01404a
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C17 H14 I N O5'
_chemical_formula_sum            'C17 H14 I N O5'
_chemical_formula_weight         439.19
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-05-12
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.523(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7835(4)
_cell_length_b                   8.1115(3)
_cell_length_c                   19.3202(7)
_cell_measurement_reflns_used    2971
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7840
_cell_measurement_theta_min      3.6600
_cell_volume                     1689.87(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0206970000
_diffrn_orient_matrix_UB_12      0.0740671000
_diffrn_orient_matrix_UB_13      -0.0155721000
_diffrn_orient_matrix_UB_21      0.0486511000
_diffrn_orient_matrix_UB_22      -0.0439007000
_diffrn_orient_matrix_UB_23      -0.0162395000
_diffrn_orient_matrix_UB_31      -0.0391559000
_diffrn_orient_matrix_UB_32      -0.0153025000
_diffrn_orient_matrix_UB_33      -0.0290017000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71000
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6557
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.28
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.921
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.863
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0324P)^2^+0.4716P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0793
_reflns_number_gt                2870
_reflns_number_total             3318
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01404a3.cif
_cod_data_source_block           zhoupx0512
_cod_depositor_comments          'Adding full bibliography for 7154140.cif.'
_cod_database_code               7154140
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C1(H1), C2(H2), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
;