Synthesis, Structural Analysis, and Chiral Investigations of Some Atropisomers with EE-Tetrahalogeno-1,3-butadiene Core
Piron, Flavia; Vanthuyne, Nicolas; Joulin, Bérangère; Naubron, Jean-Valère; Cismaş, Crina; Terec, Anamaria; Varga, Richard Attila; Roussel, Christian; Roncali, Jean; Grosu, Ion; Journal of Organic Chemistry 74 (2009) 9062–9070; doi:10.1021/jo901762j

data_4025077
_publ_section_title
;
 Synthesis, Structural Analysis, and Chiral Investigations of Some
 Atropisomers with EE-Tetrahalogeno-1,3-butadiene Core
;
_journal_coden_ASTM              JOCEAH
_journal_issue                   23
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9062
_journal_page_last               9070
_journal_paper_doi               10.1021/jo901762j
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C12 H12 Br4 N2 O4 '
_chemical_formula_sum            'C12 H12 Br4 N2 O4'
_chemical_formula_weight         567.84
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 113.885(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.162(4)
_cell_length_b                   6.3307(10)
_cell_length_c                   12.776(2)
_cell_measurement_reflns_used    2298
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      27.77
_cell_measurement_theta_min      3.24
_cell_volume                     1639.0(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0976
_diffrn_reflns_av_sigmaI/netI    0.1041
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5636
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    9.839
_exptl_absorpt_correction_T_max  0.229
_exptl_absorpt_correction_T_min  0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker, 2000.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.139
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1448
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0585
_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^)+(0.0000P)^2^+12.0293P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1486
_reflns_number_gt                1158
_reflns_number_total             1448
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901762j_si_003.cif
_cod_data_source_block           495r
_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      'C2/c  '
_cod_original_formula_sum        'C12 H12 Br4 N2 O4 '
_cod_database_code               4025077