Use of a tandem Prins/Friedel-Crafts reaction in the construction of the indeno-tetrahydropyridine core of the haouamine alkaloids: formal synthesis of (-)-haouamine A.
Fenster, Erik; Fehl, Charlie; Aubé, Jeffrey; Organic letters 13 (2011) 2614–2617; doi:10.1021/ol200725m

data_1502161
_publ_section_title
;
 Use of a tandem Prins/Friedel-Crafts reaction in the construction of the
 indeno-tetrahydropyridine core of the haouamine alkaloids: formal
 synthesis of (-)-haouamine A.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2614
_journal_page_last               2617
_journal_paper_doi               10.1021/ol200725m
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C20 H22 O2'
_chemical_formula_weight         294.38
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 95.312(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   30.462(2)
_cell_length_b                   13.2317(8)
_cell_length_c                   7.6817(5)
_cell_measurement_reflns_used    5247
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.52
_cell_measurement_theta_min      3.64
_cell_volume                     3082.9(3)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Helios high-brilliance multilayer optics'
_diffrn_radiation_source         'Bruker MicroSTAR microfocus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            17267
_diffrn_reflns_theta_full        69.41
_diffrn_reflns_theta_max         69.41
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.6419
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.678
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         5563
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0971
_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^)+(0.0956P)^2^+25.8402P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2769
_refine_ls_wR_factor_ref         0.2837
_reflns_number_gt                4658
_reflns_number_total             5563
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol200725m_si_004.cif
_cod_data_source_block           q78a
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3083.0(3)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1502161