Indium-catalyzed [1 + n] annulation reaction between beta-ketoester and alpha,omega-diyne.
Tsuji, Hayato; Tanaka, Iku; Endo, Kohei; Yamagata, Ken-Ichi; Nakamura, Masaharu; Nakamura, Eiichi; Organic letters 11 (2009) 1845–1847; doi:10.1021/ol9003542

data_1503844
_publ_section_title
;
 Indium-catalyzed [1 + n] annulation reaction between beta-ketoester and
 alpha,omega-diyne.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1845
_journal_page_last               1847
_journal_paper_doi               10.1021/ol9003542
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C25 H22 Br2 O3'
_chemical_formula_sum            'C25 H22 Br2 O3'
_chemical_formula_weight         530.25
_chemical_melting_point          434.5(5)
_chemical_name_common            spirofluorene
_chemical_name_systematic
; 
ethyl 4-acetyl-2',7'-dibromo-3,5-dimethylenespiro[cyclohexane-1,9'-fluorene]-
4-carboxylate 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.155(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.926(3)
_cell_length_b                   26.359(9)
_cell_length_c                   12.135(5)
_cell_measurement_reflns_used    7271
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.4835
_cell_measurement_theta_min      3.1879
_cell_volume                     2187.2(15)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2000)'
_computing_molecular_graphics    'ORTEP III (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXL-97 and Yadokari-XG (Wakita, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 14.5666
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device
;
Mercury CCD (2x2 bin mode)
;
_diffrn_measurement_method       dtintegrate.ref
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
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_diffrn_reflns_limit_k_min       -31
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_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.28
_exptl_absorpt_coefficient_mu    3.731
_exptl_absorpt_correction_T_max  0.6045
_exptl_absorpt_correction_T_min  0.2570
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.15
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_refine_ls_extinction_method     none
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_refine_ls_number_reflns         4062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0246
_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^)+(0.0234P)^2^+1.9252P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0564
_refine_ls_wR_factor_ref         0.0565
_reflns_number_gt                4039
_reflns_number_total             4062
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol9003542_si_002.cif
_cod_data_source_block           it1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '434-435' was changed to '434.5(5)' -
the average value was taken and precision was
estimated.

'_exptl_absorpt_correction_type' value 'Numerical'
changed to 'numerical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2187.1(14)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1503844