A torquoselective 6π electrocyclization approach to reserpine alkaloids.
Barcan, Gregg A.; Patel, Ashay; Houk, K. N.; Kwon, Ohyun; Organic letters 14 (2012) 5388–5391; doi:10.1021/ol302265z

data_1508664
_publ_section_title
;
 A torquoselective 6\p electrocyclization approach to reserpine alkaloids.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5388
_journal_page_last               5391
_journal_paper_doi               10.1021/ol302265z
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C25 H29 Br N2 O5'
_chemical_formula_sum            'C25 H29 Br N2 O5'
_chemical_formula_weight         517.41
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 96.813(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.842(5)
_cell_length_b                   6.0050(19)
_cell_length_c                   24.945(8)
_cell_measurement_reflns_used    3331
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.79
_cell_measurement_theta_min      3.69
_cell_volume                     2356.3(13)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.979
_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  0.0749
_diffrn_reflns_av_sigmaI/netI    0.0621
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            30828
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         29.50
_diffrn_reflns_theta_min         3.63
_exptl_absorpt_coefficient_mu    1.784
_exptl_absorpt_correction_T_max  0.9161
_exptl_absorpt_correction_T_min  0.5687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Bruker)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.418
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         6434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0335P)^2^+0.5791P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                4635
_reflns_number_total             6434
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302265z_si_002.cif
_cod_data_source_block           kw112s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        2356.2(13)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1508664