Synthesis and structural analysis of a novel iodinated cyclopentadienone via ring-contraction iodination and its application in synthesis of alkyne-functionalized cyclopentadienones.
Chen, Xue-Yi; Barnes, Charles; Bai, Xinyan; Sandreczki, T. C.; Peng, Zhonghua; Kadnikova, Ekaterina N.; Dias, J. R.; Chemical communications (Cambridge, England) 46 (2010) 8171–8173; doi:10.1039/c0cc02543g

data_7112967
_publ_section_title
;
 Synthesis and structural analysis of a novel iodinated cyclopentadienone
 via ring-contraction iodination and its application in synthesis of
 alkyne-functionalized cyclopentadienones.
;
_journal_issue                   43
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8171
_journal_page_last               8173
_journal_paper_doi               10.1039/c0cc02543g
_journal_volume                  46
_journal_year                    2010
_chemical_formula_sum            'C18 H25 I O4'
_chemical_formula_weight         432.28
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 125.523(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.726(5)
_cell_length_b                   9.7110(17)
_cell_length_c                   18.526(3)
_cell_measurement_reflns_used    9863
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.5
_cell_measurement_theta_min      2.2
_cell_volume                     3766.9(12)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2008)'
_computing_data_collection       'APEX2 (Bruker AXS, 2008)'
_computing_data_reduction        'APEX2 (Bruker AXS, 2008)'
_computing_molecular_graphics    'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            21540
_diffrn_reflns_theta_full        28.69
_diffrn_reflns_theta_max         28.69
_diffrn_reflns_theta_min         2.23
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    1.717
_exptl_absorpt_correction_T_max  0.63
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Data were corrected for decay and absorption using the program SADABS
(Sheldrick, G. M. (2003). SADABS. Version 2.10. University of
G\"ottingen, Germany).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.763
_refine_diff_density_min         -0.899
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         4586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0211
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0270P)^2^+4.4593P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0560
_refine_ls_wR_factor_ref         0.0574
_reflns_number_gt                4228
_reflns_number_total             4586
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0cc02543g.txt
_cod_data_source_block           tB2AcPhI-m
_cod_original_cell_volume        3766.9(11)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7112967