Synthesis of (+)-CP-99,994 via Pd(0)-Catalyzed Asymmetric Allylic and Homoallylic C-H Diamination of Terminal Olefin
Renzhong Fu; Baoguo Zhao; Yian Shi; Journal of Organic Chemistry 74 (2009) 7577–7580; doi:10.1021/jo9015584

data_4024888
_publ_section_title
;
Synthesis of (+)-CP-99,994 via Pd(0)-Catalyzed Asymmetric Allylic and
Homoallylic C-H Diamination of Terminal Olefin
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7577
_journal_page_last               7580
_journal_paper_doi               10.1021/jo9015584
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration rm
_chemical_formula_sum            'C19 H26 Cl2 N2 O'
_chemical_formula_weight         369.32
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'Bruker SHELXTL'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.7519(8)
_cell_length_b                   11.0762(14)
_cell_length_c                   24.916(4)
_cell_measurement_reflns_used    1341
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.45
_cell_measurement_theta_min      2.46
_cell_volume                     1863.4(4)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_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  0.0993
_diffrn_reflns_av_sigmaI/netI    0.2467
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            19163
_diffrn_reflns_theta_full        36.32
_diffrn_reflns_theta_max         36.32
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.357
_exptl_absorpt_correction_T_max  0.9724
_exptl_absorpt_correction_T_min  0.9154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sheldrick, 1997'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       RECTANGLE
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.103
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.15(9)
_refine_ls_extinction_coef       0.0091(19)
_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   0.888
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         8849
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.888
_refine_ls_R_factor_all          0.2057
_refine_ls_R_factor_gt           0.0764
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0776P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1980
_reflns_number_gt                3750
_reflns_number_total             8849
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9015584_si_001.cif
_cod_data_source_block           ys189b_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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)2(1)2(1)
_cod_database_code               4024888