Double-Mannich annulation of cyclic ketones using N,N-Bis(ethoxymethyl)alkylamine reagents.
Halliday, Jill I.; Chebib, Mary; Turner, Peter; McLeod, Malcolm D.; Organic letters 8 (2006) 3399–3401; doi:10.1021/ol061242s

data_1506111
_publ_section_title
;
 Double-Mannich annulation of cyclic ketones using
 N,N-Bis(ethoxymethyl)alkylamine reagents.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3399
_journal_page_last               3401
_journal_paper_doi               10.1021/ol061242s
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C13 H25 N O'
_chemical_formula_weight         211.34
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                65.224(2)
_cell_angle_beta                 68.024(2)
_cell_angle_gamma                67.455(2)
_cell_formula_units_Z            6
_cell_length_a                   13.1985(15)
_cell_length_b                   13.4944(15)
_cell_length_c                   13.9409(16)
_cell_measurement_reflns_used    971
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.74
_cell_measurement_theta_min      2.75
_cell_volume                     2013.5(4)
_computing_cell_refinement       'SAINT (Bruker,1995)'
_computing_data_collection       'SMART (Bruker,1995)'
_computing_data_reduction        'SAINT and XPREP (Bruker 1995)'
_computing_molecular_graphics
;
  xtal 3.6 (Hall,du Boulay, D.J. & Olthof-Hazekamp, R. 1999)
  ORTEPII  (Johnson,C.K., 1976). 
  WinGX (Farrugia, 1999)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, et. al. 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_crystal_treatment
;
 attached to a thin glass fibre
;
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20119
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.73
_diffrn_standards_decay_%        0.03
_diffrn_standards_number         135
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.046
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.518
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.324
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0175(19)
_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   1.381
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         9373
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.381
_refine_ls_R_factor_all          0.1147
_refine_ls_R_factor_gt           0.0814
_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^)+(0.05P)^2^+0.50P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2031
_refine_ls_wR_factor_ref         0.2188
_reflns_number_gt                5698
_reflns_number_total             9373
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol061242ssi20060521_093044.cif
_cod_data_source_block           mdm2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 
;
_cod_original_sg_symbol_H-M      'P -1       '
_cod_database_code               1506111