Construction of the Azocane (Azacyclooctane) Moiety of the Lycopodium Alkaloid Lycopladine H via an Intramolecular Hydroaminomethylation Strategy.
Sacher, Joshua R.; Weinreb, Steven M.; Organic letters 14 (2012) 2172–2175; doi:10.1021/ol3007277

data_1507635
_publ_section_title
;
 Construction of the Azocane (Azacyclooctane) Moiety of the Lycopodium
 Alkaloid Lycopladine H via an Intramolecular Hydroaminomethylation
 Strategy.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              2172
_journal_page_last               2175
_journal_paper_doi               10.1021/ol3007277
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C11 H13 Br N O5'
_chemical_formula_sum            'C11 H13 Br N O5'
_chemical_formula_weight         319.13
_chemical_name_systematic
; 
 ? 
;
_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                 96.024(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.818(3)
_cell_length_b                   12.852(4)
_cell_length_c                   23.452(7)
_cell_measurement_reflns_used    5356
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.384
_cell_measurement_theta_min      2.322
_cell_volume                     2643.1(15)
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            21104
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    3.122
_exptl_absorpt_correction_T_max  0.5740
_exptl_absorpt_correction_T_min  0.4751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.759
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         6535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0768P)^2^+1.0928P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1356
_reflns_number_gt                4670
_reflns_number_total             6535
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3007277_si_002.cif
_cod_data_source_block           jrs5s
_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        2643.3(14)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1507635