Formal [4 + 1]- and [5 + 1]-annulation by an s(n)2-conjugate addition sequence: stereoselective synthesis of highly substituted carbocycles.
Tong, Benny Meng Kiat; Chen, Hui; Chong, Sin Yee; Heng, Yi Li; Chiba, Shunsuke; Organic letters 14 (2012) 2826–2829; doi:10.1021/ol301044e

data_1507737
_publ_contact_author
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Dr Shunsuke Chiba
Division of Chemistry and Biological Chemistry
School of Physical and Mathematical Sciences
Nanyang Technological University
21 Nanyang Link
Singapore 637371
Singapore
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_publ_section_title
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 Formal [4 + 1]- and [5 + 1]-annulation by an s(n)2-conjugate addition
 sequence: stereoselective synthesis of highly substituted carbocycles.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2826
_journal_page_last               2829
_journal_paper_doi               10.1021/ol301044e
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C17 H21 N O4 S'
_chemical_formula_sum            'C17 H21 N O4 S'
_chemical_formula_weight         335.41
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                102.820(2)
_cell_angle_beta                 98.634(2)
_cell_angle_gamma                97.615(2)
_cell_formula_units_Z            2
_cell_length_a                   7.5986(6)
_cell_length_b                   10.3898(7)
_cell_length_c                   11.2916(9)
_cell_measurement_reflns_used    6679
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      30.99
_cell_measurement_theta_min      2.75
_cell_volume                     846.57(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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      103(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \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  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13000
_diffrn_reflns_theta_full        31.13
_diffrn_reflns_theta_max         31.13
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  0.9396
_exptl_absorpt_correction_T_min  0.9206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         5389
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.173
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0675P)^2^+0.1579P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1245
_reflns_number_gt                4593
_reflns_number_total             5389
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301044e_si_003.cif
_cod_data_source_block           3cd
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1507737