One-pot Biomimetic Total Synthesis of Yuehchukene via the Organocatalytic Alkylation-cyclization Process of a Sterically Encumbered α-Alkyl Enal
Dange, Nitin S.; HONG, BOR-CHERNG; Lee, Gene-Hsiang; RSC Adv.  (2014) –; doi:10.1039/C4RA10222C

data_7218679
_publ_section_title
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 One-pot Biomimetic Total Synthesis of Yuehchukene via the Organocatalytic
 Alkylation-cyclization Process of a Sterically Encumbered \a-Alkyl Enal
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA10222C
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H25 N O3'
_chemical_formula_weight         327.41
_chemical_name_systematic        ()-trans-NSD-09-184-F1
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6171(3)
_cell_length_b                   11.0858(3)
_cell_length_c                   14.9945(3)
_cell_measurement_reflns_used    11449
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.28
_cell_volume                     1764.84(8)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       'NONIUS COLLECT'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'NONIUS KappaCCD'
_diffrn_measurement_method       '\w 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  0.0566
_diffrn_reflns_av_sigmaI/netI    0.0830
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11449
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_correction_T_min  0.9758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.7(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.882
_refine_ls_hydrogen_treatment    mconstr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         4036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.882
_refine_ls_R_factor_all          0.1141
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0565P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1123
_reflns_number_gt                2140
_reflns_number_total             4036
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra10222c2.cif
_cod_data_source_block           ic16762
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/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 2827 2014-09-09 07:05:25Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7218679