Dimethyl sulfide induced [3+2] annulation strategy: an efficient synthesis of functionalized dihydropyrazole derivatives using the Baylis-Hillman bromides.
Basavaiah, Deevi; Roy, Suparna; Organic letters 10 (2008) 1819–1821; doi:10.1021/ol800424v

data_1504631
_publ_section_title
;
 Dimethyl sulfide induced [3+2] annulation strategy: an efficient
 synthesis of functionalized dihydropyrazole derivatives using the
 Baylis-Hillman bromides.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              1819
_journal_page_last               1821
_journal_paper_doi               10.1021/ol800424v
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C18 H21 Br N2 O6'
_chemical_formula_sum            'C18 H21 Br N2 O6'
_chemical_formula_weight         441.28
_chemical_melting_point          130(2)
_chemical_name_systematic
; 
 3-(4-Bromophenyl)-1,2-bis(isopropoxycarbonyl)-
2,3-dihydro-1H-pyrazole-4-carboxylic acid    
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.4070(10)
_cell_angle_beta                 91.4570(10)
_cell_angle_gamma                116.6200(10)
_cell_formula_units_Z            2
_cell_length_a                   9.9179(8)
_cell_length_b                   9.9305(8)
_cell_length_c                   12.1617(10)
_cell_measurement_temperature    298
_cell_volume                     1024.11(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows/Platon'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10443
_diffrn_reflns_theta_full        25.80
_diffrn_reflns_theta_max         25.80
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    2.042
_exptl_absorpt_correction_T_max  0.7493
_exptl_absorpt_correction_T_min  0.6293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABAS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0460P)^2^+0.3138P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1110
_reflns_number_gt                2403
_reflns_number_total             3900
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol800424v-file005.cif
_cod_data_source_block           7
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               1504631