A mild and efficient method for the synthesis of a new optically active diallyl selenide and its catalytic activity in the allylic chlorination of natural terpenes
Boualy, Brahim; El Houssame, Soufiane; Sancineto, Luca; Santi, Claudio; Ait Ali, Mustapha; Stoeckli-Evans, Helen; El Firdoussi, Larbi; New J. Chem. 40 (2016) 3395–; doi:10.1039/C5NJ02797G

data_7055352
_publ_section_title
;
 A mild and efficient method for the synthesis of a new optically active
 diallyl selenide and its catalytic activity in the allylic chlorination
 of natural terpenes
;
_journal_issue                   4
_journal_name_full               'New J. Chem.'
_journal_page_first              3395
_journal_paper_doi               10.1039/C5NJ02797G
_journal_volume                  40
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C20 H30 Se'
_chemical_formula_sum            'C20 H30 Se'
_chemical_formula_weight         349.40
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-10-10 deposited with the CCDC.
2016-02-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.314(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.4153(8)
_cell_length_b                   6.8490(7)
_cell_length_c                   12.4992(12)
_cell_measurement_reflns_used    6934
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.03
_cell_measurement_theta_min      1.74
_cell_volume                     916.45(15)
_computing_cell_refinement       'X-Area V1.52'
_computing_data_collection       'X-Area V1.52 (Stoe & Cie, 2009)'
_computing_data_reduction        'X-RED32 V1.48 (Stoe & Cie, 2009)'
_computing_molecular_graphics
'PLATON  (Spek, 2009) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXL-97, PLATON and Publcif (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       '\f + \w scans'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4842
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.59
_diffrn_reflns_theta_min         1.74
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.042
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'MULscanABS in PLATON (Spek, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.012(9)
_refine_ls_extinction_coef       0.0067(10)
_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   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     99
_refine_ls_number_reflns         1710
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0200
_refine_ls_R_factor_gt           0.0195
_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^)+(0.0259P)^2^+0.3056P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0457
_refine_ls_wR_factor_ref         0.0458
_reflns_number_gt                1695
_reflns_number_total             1710
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c5nj02797g1.cif
_cod_data_source_block           BB-6
_cod_depositor_comments          'Adding full bibliography for 7055352.cif.'
_cod_original_cell_volume        916.45(14)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7055352