Experimental Studies on the Selective β-C-H Halogenation of Enones.
Huber, Tatjana; Kaiser, Daniel; Rickmeier, Jens; Magauer, Thomas; The Journal of organic chemistry 80 (2015) 2281–2294; doi:10.1021/jo502809d

data_4030612
_publ_section_title
;
 Experimental Studies on the Selective \b-C-H Halogenation of Enones.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2281
_journal_page_last               2294
_journal_paper_doi               10.1021/jo502809d
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C11 H17 Br N2 O2'
_chemical_formula_sum            'C11 H17 Br N2 O2'
_chemical_formula_weight         289.169
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_block_code                C11H17BrN2O2_sv004_magauer
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             03-Mar-14
_cell_angle_alpha                97.002(10)
_cell_angle_beta                 92.212(9)
_cell_angle_gamma                103.538(10)
_cell_formula_units_Z            2
_cell_length_a                   5.909(2)
_cell_length_b                   9.420(3)
_cell_length_c                   12.251(4)
_cell_measurement_reflns_used    99
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      21.4697
_cell_measurement_theta_min      5.0416
_cell_volume                     656.4(4)
_computing_cell_refinement       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v3.0.21'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_refinement
;
Sheldrick, G. M. (2008).
<i>Acta Cryst.</i> A<b>64</b>, 112--122.
;
_computing_structure_solution
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8Venture'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_radiation_collimation    0.8_mm
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1845
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2416
_diffrn_reflns_theta_full        25.30
_diffrn_reflns_theta_max         25.13
_diffrn_reflns_theta_min         3.36
_diffrn_source_current           50
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    3.121
_exptl_absorpt_correction_T_max  0.9579
_exptl_absorpt_correction_T_min  0.5932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
TWINABS embedded in Saint
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.4631(9)
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.117
_exptl_crystal_size_mid          0.029
_exptl_crystal_size_min          0.027
_refine_diff_density_max         1.496
_refine_diff_density_min         -0.729
_refine_diff_density_rms         0.221
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2454
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.1943
_refine_ls_R_factor_gt           0.1051
_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^)+(0.1577P)^2^+1.6742P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2586
_refine_ls_wR_factor_ref         0.3029
_reflns_number_gt                1438
_reflns_number_total             2454
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502809d_si_002.cif
_cod_data_source_block           sv004
_cod_depositor_comments          'Adding full bibliography for 4030612.cif.'
_cod_database_code               4030612