Halo Substituent Effects on Intramolecular Cycloadditions Involving Furanyl Amides
Albert Padwa; Kenneth R. Crawford; Christopher S. Straub; Susan N. Pieniazek; K. N. Houk; Journal of Organic Chemistry 71 (2006) 5432–5439; doi:10.1021/jo0602322

data_4021809
_publ_section_title
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 Halo Substituent Effects on Intramolecular Cycloadditions
 Involving Furanyl Amides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5432
_journal_page_last               5439
_journal_paper_doi               10.1021/jo0602322
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C16 H17 N O2 Cl Br'
_chemical_formula_sum            'C16 H17 Br Cl N O2'
_chemical_formula_weight         370.67
_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                 92.532(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.6959(10)
_cell_length_b                   9.2239(6)
_cell_length_c                   36.216(3)
_cell_measurement_reflns_used    29
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      10.65
_cell_volume                     3235.8(5)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            5873
_diffrn_reflns_theta_full        56.75
_diffrn_reflns_theta_max         56.75
_diffrn_reflns_theta_min         2.44
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.012
_exptl_absorpt_correction_T_max  0.1606
_exptl_absorpt_correction_T_min  0.0516
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       triangular_block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.00059(8)
_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   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         4270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0460
_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^)+(0.0615P)^2^+0.8030P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1266
_reflns_number_gt                3195
_reflns_number_total             4270
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0602322si20060205_013943.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4021809