Scandium-catalyzed tandem selective oxirane ring-opening/Friedel-Crafts alkylation: a facile access to [1,4]oxazino[4,3-a]indoles and 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazines.
Wei, Lai; Liu, Lu; Zhang, Junliang; Organic & biomolecular chemistry 12 (2014) 6869–6877; doi:10.1039/c4ob01057d

data_7153950
_publ_section_title
;
 Scandium-catalyzed tandem selective oxirane ring-opening/Friedel-Crafts
 alkylation: a facile access to [1,4]oxazino[4,3-a]indoles and
 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazines.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6869
_journal_page_last               6877
_journal_paper_doi               10.1039/c4ob01057d
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C18 H14 Br N O2'
_chemical_formula_weight         356.21
_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                 93.670(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9849(8)
_cell_length_b                   8.8043(6)
_cell_length_c                   14.3967(10)
_cell_measurement_temperature    296(2)
_cell_volume                     1516.01(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16981
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    2.718
_exptl_absorpt_correction_T_max  0.5616
_exptl_absorpt_correction_T_min  0.4412
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2675
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0454P)^2^+1.2011P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.1024
_reflns_number_gt                2068
_reflns_number_total             2675
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01057d2.cif
_cod_data_source_block           z
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 7153950.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7153950