An Experimental and Theoretical Study of the Asymmetric Lithiation of 1,2,3,5,6,7-Hexahydro-3a,4a-diazacyclopenta[def]phenanthren-4-one
Costa Metallinos; Travis Dudding; Josh Zaifman; Jennifer L. Chaytor; Nicholas J. Taylor; Journal of Organic Chemistry 72 (2007) 957–963; doi:10.1021/jo062244t

data_4022721
_publ_section_title
;
 An Experimental and Theoretical Study of the Asymmetric Lithiation
 of 1,2,3,5,6,7-Hexahydro-3a,4a-diazacyclopenta[def]phenanthren-4-one
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              957
_journal_page_last               963
_journal_paper_doi               10.1021/jo062244t
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C14 H14 Br2 N2 O'
_chemical_formula_weight         386.09
_space_group_IT_number           1
_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                63.330(1)
_cell_angle_beta                 85.655(1)
_cell_angle_gamma                72.561(1)
_cell_formula_units_Z            2
_cell_length_a                   7.7309(3)
_cell_length_b                   9.8742(4)
_cell_length_c                   10.3592(4)
_cell_measurement_reflns_used    6566
_cell_measurement_temperature    180(1)
_cell_measurement_theta_max      34.97
_cell_measurement_theta_min      2.42
_cell_volume                     672.57(5)
_computing_cell_refinement       SAINT
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      180(1)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       Omega
_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  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7506
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    6.019
_exptl_absorpt_correction_T_max  0.628
_exptl_absorpt_correction_T_min  0.330
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Face-indexed analytical'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.906
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Triangular needle fragment'
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.017(6)
_refine_ls_extinction_coef       0.0165(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.300
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         6709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.300
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0259
_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^)+(0.0100P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0484
_refine_ls_wR_factor_ref         0.0487
_reflns_number_gt                6187
_reflns_number_total             6709
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062244trom20061030_025138.cif
_cod_data_source_block           cm1345am
_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.

'_exptl_absorpt_correction_type' value 'Integration' changed
to 'integration' 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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4022721