Substituent effects on stereoselectivity of dihalocarbene reactions with cyclohexadiene and on the reactivity of bis-dihalocyclopropanes in electrophilic nitrations on route to pyrimidine N-oxides
Sedenkova, Kseniya N.; Averina, Elena B.; Grishin, Y K.; Kolodjashnaja, Julia V.; Rybakov, Victor B.; Kuznetsova, Tamara S.; Hughes, Audrey; Gomes, Gabriel dos Passos; Alabugin, Igor; Zefirov, Nikolay S.; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB02463K

data_7155929
_publ_section_title
;
 Substituent effects on stereoselectivity of dihalocarbene reactions with
 cyclohexadiene and on the reactivity of bis-dihalocyclopropanes in
 electrophilic nitrations on route to pyrimidine N-oxides
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB02463K
_journal_year                    2017
_chemical_formula_moiety         'C8 H8 Br2 F2'
_chemical_formula_sum            'C8 H8 Br2 F2'
_chemical_formula_weight         301.94
_chemical_melting_point_gt       409
_chemical_melting_point_lt       411
_chemical_name_systematic
; 
 4,8--Dibromo--4,8--difluorotricyclo[5.1.0.0^3,5^]octane 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_audit_update_record
;
2014-01-30 deposited with the CCDC.
2017-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.172(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.2656(6)
_cell_length_b                   6.3728(4)
_cell_length_c                   11.8196(12)
_cell_measurement_reflns_used    8270
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.60
_cell_measurement_theta_min      3.19
_cell_volume                     464.53(7)
_computing_cell_refinement       '<i>X--AREA</i>  (STOE & CIE, 2012)'
_computing_data_collection       '<i>X--AREA</i>  (STOE & CIE, 2012)'
_computing_data_reduction        '<i>X--RED</i>   (STOE & CIE, 2012)'
_computing_molecular_graphics    '<i>Ortep--3</i> (Farrugia,   1997)'
_computing_publication_material  '<i>WinGX</i>    (Farrugia,   1999)'
_computing_structure_refinement  '<i>SHELXL97</i> (Sheldrick,  2008)'
_computing_structure_solution    '<i>SHELXS97</i> (Sheldrick,  2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'Hybride pixel array detector'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS Pilatus--100K'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Four cyrcle diffractometer'
_diffrn_measurement_device_type  STADI--VARY
_diffrn_measurement_method       'Rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'Plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_source         'LFF Sealed Tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0934
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            969
_diffrn_reflns_theta_full        26.70
_diffrn_reflns_theta_max         26.70
_diffrn_reflns_theta_min         3.45
_diffrn_source                   'SEIFERT Iso--Debyeflex 3003'
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    8.697
_exptl_absorpt_correction_T_max  0.1706
_exptl_absorpt_correction_T_min  0.0640
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
 Parkin, Moezzi & Hope. (1995). J. Appl. Cryst. 28, 53-56
 Cubic fit to sin(theta)/lambda - 24 parameters
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    2.159
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             288
_exptl_crystal_preparation       'petroleum ether'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.936
_refine_diff_density_min         -1.089
_refine_diff_density_rms         0.210
_refine_ls_extinction_coef       0.029(6)
_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   0.938
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     56
_refine_ls_number_reflns         969
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0615
_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^)+(0.0799P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1463
_reflns_number_gt                671
_reflns_number_total             969
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c7ob02463k2.cif
_cod_data_source_block           aver92
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7155929
_exptl_absorpt_factor_mur        2.174
_exptl_absorpt_correction_t_ave  0.1178
_exptl_absorpt_rmerge_before     0.1047
_exptl_absorpt_rmerge_after      0.0798