Nucleophilic heterocyclic carbene catalyzed annulation of enals to chalcones in methanol: a stereoselective synthesis of highly functionalized cyclopentanes.
Nair, Vijay; Babu, Beneesh P.; Vellalath, Sreekumar; Varghese, Vimal; Raveendran, Anabha E.; Suresh, Eringathodi; Organic letters 11 (2009) 2507–2510; doi:10.1021/ol900571x

data_1503901
_publ_section_title
;
 Nucleophilic heterocyclic carbene catalyzed annulation of enals to
 chalcones in methanol: a stereoselective synthesis of highly
 functionalized cyclopentanes.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2507
_journal_page_last               2510
_journal_paper_doi               10.1021/ol900571x
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C26 H25 Br O4'
_chemical_formula_weight         481.37
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 111.168(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.672(11)
_cell_length_b                   6.034(3)
_cell_length_c                   18.445(9)
_cell_measurement_temperature    293(2)
_cell_volume                     2249.3(19)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    ORTEP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.498
_diffrn_measured_fraction_theta_max 0.498
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0895
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_diffrn_reflns_limit_l_min       -21
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_exptl_absorpt_correction_T_max  0.9294
_exptl_absorpt_correction_T_min  0.4630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.49
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_exptl_crystal_size_min          0.04
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
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_refine_ls_extinction_method     none
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_refine_ls_number_reflns         2176
_refine_ls_number_restraints     1
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_refine_ls_R_factor_all          0.1355
_refine_ls_R_factor_gt           0.0784
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0747P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1653
_reflns_number_gt                1306
_reflns_number_total             2176
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900571x_si_002.cif
_cod_data_source_block           462pbbm
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' 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 

The following automatic conversions were performed:

data name '_exptl_absorpt_process_detail' was replaced with
'_exptl_absorpt_process_details' as specified in the replacement file
'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_cell_volume        2249(2)
_cod_original_sg_symbol_H-M      C2
_cod_database_code               1503901