Rapid construction of the aza-propellane core of acutumine via a photochemical [2 + 2] cycloaddition reaction.
Navarro, Raul; Reisman, Sarah E.; Organic letters 14 (2012) 4354–4357; doi:10.1021/ol3017963

data_1508593
_publ_section_title
;
 Rapid construction of the aza-propellane core of acutumine via a
 photochemical [2 + 2] cycloaddition reaction.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4354
_journal_page_last               4357
_journal_paper_doi               10.1021/ol3017963
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H20 Br N O4 , H2 O'
_chemical_formula_sum            'C16 H22 Br N O5'
_chemical_formula_weight         388.26
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2279(3)
_cell_length_b                   12.4336(5)
_cell_length_c                   17.6522(7)
_cell_measurement_reflns_used    9272
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.62
_cell_measurement_theta_min      2.31
_cell_volume                     1586.38(11)
_computing_cell_refinement       'SAINT V7.68A (Bruker-AXS, 2007)'
_computing_data_collection       'APEX2 v2010.7-0 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT V7.68A (Bruker-AXS, 2007)'
_computing_molecular_graphics    'Bruker XP v5.1'
_computing_publication_material  'Bruker XCIF 2008'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker KAPPA APEX II'
_diffrn_measurement_method       '\w scans; 10 settings'
_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  0.0867
_diffrn_reflns_av_sigmaI/netI    0.0692
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            40470
_diffrn_reflns_theta_full        32.34
_diffrn_reflns_theta_max         32.34
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    2.617
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.50
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker-AXS, 2001)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.358
_refine_diff_density_min         -1.303
_refine_diff_density_rms         0.112
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.015(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.534
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         5378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.534
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'calc w=1/[\s^2^(Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0744
_refine_ls_wR_factor_ref         0.0768
_reflns_number_gt                4263
_reflns_number_total             5378
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3017963_si_003.cif
_cod_data_source_block           run03
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1508593