Synthesis of 2,3-Dihydro-10bH-oxazolo[2,3-a]isoquinolines from ortho-Lithiated Phenyloxazolinyloxiranes
Vito Capriati; Saverio Florio; Renzo Luisi; Filippo Maria Perna; Journal of Organic Chemistry 72 (2007) 6316–6319; doi:10.1021/jo070708x

data_4024090
_publ_contact_author
;Prof. Saverio Florio

;
_publ_contact_author_address
;Dipartimento Farmaco-Chimico
Universit\`a degli Studi di Bari
via E. Orabona 4
70125 Bari Ba
Italy
;
_publ_contact_author_email       florio@farmchim.uniba.it
_publ_contact_author_fax         '39 080 5442231'
_publ_contact_author_phone       '39 080 5442749'
_publ_section_title
;
 Synthesis of 2,3-Dihydro-10bH-oxazolo[2,3-a]isoquinolines
 from ortho-Lithiated Phenyloxazolinyloxiranes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6316
_journal_page_last               6319
_journal_paper_doi               10.1021/jo070708x
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C14 H17 N O2'
_chemical_formula_weight         231.29
_chemical_melting_point          115
_chemical_name_systematic
;
  2,4',4'-Trimethyl-2,3-dihydrospiro(2,3-epoxy-indene-1,2'-[1,3]-oxazolidine)
;
_space_group_IT_number           45
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'I 2 -2c'
_symmetry_space_group_name_H-M   'I b a 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.3485(5)
_cell_length_b                   16.3317(4)
_cell_length_c                   8.5750(2)
_cell_measurement_reflns_used    9008
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.18
_cell_measurement_theta_min      1.67
_cell_volume                     2569.60(11)
_computing_cell_refinement
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD (Bruker-Nonius, 1998)'
_computing_data_reduction
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Phi scan'
_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  0.031
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9008
_diffrn_reflns_theta_full        26.18
_diffrn_reflns_theta_max         26.18
_diffrn_reflns_theta_min         2.49
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          .5
_exptl_crystal_size_mid          .5
_exptl_crystal_size_min          .15
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.105
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.3(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1320
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0301
_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^)+(0.0516P)^2^+0.4011P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0837
_reflns_number_gt                1267
_reflns_number_total             1320
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070708xsi20070419_055027.cif
_cod_data_source_block           shelxl
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4024090