Substitution Effect on the Cylization/Fluorination Reaction of N-Dienes in Superacid
Emilie Vardelle; Agnès Martin-Mingot; Marie-Paule Jouannetaud; Christian Bachmann; Jérôme Marrot; Sébastien Thibaudeau; Journal of Organic Chemistry 74 (2009) 6025–6034; doi:10.1021/jo900881f

data_4024753
_publ_contact_author
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      Dr S. Thibaudeau
      Laboratoire Synth\`ese et r\'eactivit\'e des Substances naturelles
      UMR 6514, Universit\'e de Poitiers
      40,Avenue du Recteur Pineau, F-86022 Poitiers Cedex
      France
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_publ_contact_author_email       sebastien.thibaudeau@univ-poitiers.fr
_publ_contact_author_fax         '(33) 05 49 45 35 01'
_publ_contact_author_phone       '(33) 05 49 45 45 88'
_publ_section_title
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Substitution Effect on the Cylization/Fluorination Reaction of N-Dienes in
Superacid
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6025
_journal_page_last               6034
_journal_paper_doi               10.1021/jo900881f
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C13 H16 Cl F N2 O2'
_chemical_formula_weight         286.73
_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                 95.475(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.867(5)
_cell_length_b                   9.840(3)
_cell_length_c                   9.475(3)
_cell_measurement_reflns_used    5594
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.35
_cell_measurement_theta_min      2.99
_cell_volume                     1379.7(8)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 512x512
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16961
_diffrn_reflns_theta_full        23.99
_diffrn_reflns_theta_max         23.99
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_correction_T_min  0.9608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2.10)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.670
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.10(3)
_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   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2124
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0689
_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^)+(0.0935P)^2^+1.7239P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1783
_refine_ls_wR_factor_ref         0.1802
_reflns_number_gt                1751
_reflns_number_total             2124
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900881f_si_001_2.cif
_cod_data_source_block           7e
_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 
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_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4024753