Stereoselective preparation of conjugated (Z)-1,3-enynes by dehydration reactions of allenic bromohydrins and the use of the enynes in base-mediated tandem allylation ene-carbocyclization reactions with β-ketoesters.
Lin, Mei-Huey; Chen, Yu-Chun; Chiu, Shih-Hao; Liang, Kung-Yu; Lee, Yi-Lin; Chuang, Tsung-Hsun; Organic & biomolecular chemistry 15 (2017) 605–609; doi:10.1039/c6ob02178f

data_7155411
_publ_section_title
;
 Stereoselective preparation of conjugated (Z)-1,3-enynes by dehydration
 reactions of allenic bromohydrins and the use of the enynes in
 base-mediated tandem allylation ene-carbocyclization reactions with
 \b-ketoesters.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              605
_journal_page_last               609
_journal_paper_doi               10.1039/c6ob02178f
_journal_volume                  15
_journal_year                    2017
_chemical_formula_sum            'C11 H8 Br2'
_chemical_formula_weight         299.99
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-08-22 deposited with the CCDC.
2016-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.674(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.3644(3)
_cell_length_b                   15.4436(10)
_cell_length_c                   7.8210(6)
_cell_measurement_reflns_used    3673
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.321
_cell_measurement_theta_min      2.6375
_cell_volume                     519.66(6)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       /w
_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  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7121
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.64
_exptl_absorpt_coefficient_mu    7.748
_exptl_absorpt_correction_T_max  0.4566
_exptl_absorpt_correction_T_min  0.3361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.917
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.103
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.98(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.671
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2531
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.671
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0419
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1476
_reflns_number_gt                2374
_reflns_number_total             2531
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob02178f2.cif
_cod_data_source_block           lky_iii_22801
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7155409--7155411.cif.
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7155411