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_7112966
_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            'C13 H19 I O'
_chemical_formula_weight         318.18
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      62
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.0985(17)
_cell_length_b                   8.0587(7)
_cell_length_c                   9.1236(8)
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.6
_cell_measurement_theta_min      2.3
_cell_volume                     1330.7(2)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0136
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14653
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.25
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    2.382
_exptl_absorpt_correction_T_max  0.54
_exptl_absorpt_correction_T_min  0.48
_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            red
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       0.0232(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     86
_refine_ls_number_reflns         1633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0156
_refine_ls_R_factor_gt           0.0151
_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^)+(0.0181P)^2^+0.6842P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0378
_refine_ls_wR_factor_ref         0.0381
_reflns_number_gt                1594
_reflns_number_total             1633
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0cc02543g.txt
_cod_data_source_block           tB2OHPhI2-m
_cod_database_code               7112966